#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:18:41 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257596 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/99/7239986.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7239986
loop_
_publ_author_name
'Pham, Thuy Trang'
'Chen, Xi'
'Söhnel, Tilo'
'Yan, Ning'
'Sperry, Jonathan'
_publ_section_title
;
 Haber-independent, diversity-oriented synthesis of nitrogen compounds
 from biorenewable chitin
;
_journal_issue                   6
_journal_name_full               'Green Chemistry'
_journal_page_first              1978
_journal_page_last               1984
_journal_paper_doi               10.1039/D0GC00208A
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         '4(C15 H21 N O6)'
_chemical_formula_sum            'C60 H84 N4 O24'
_chemical_formula_weight         1245.31
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-01-07 deposited with the CCDC.	2020-02-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.7230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.7484(3)
_cell_length_b                   10.70600(10)
_cell_length_c                   26.2577(3)
_cell_measurement_reflns_used    38480
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      74.1160
_cell_measurement_theta_min      3.2790
_cell_volume                     6267.71(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     23.00  51.00   0.50    2.00    --   47.48  75.00  -8.00   56
  2  ω     55.00  99.00   0.50    2.00    --   47.48  75.00  -8.00   88
  3  ω     76.00 177.00   0.50   15.00    --  101.53  75.00  -8.00  202
  4  ω    143.00 176.00   0.50   15.00    --  101.53  30.00  90.00   66
  5  ω    138.00 173.00   0.50   15.00    --  101.53  61.00  90.00   70
  6  ω    110.00 155.00   0.50   15.00    --  101.53  77.00 -30.00   90
  7  ω    114.00 175.00   0.50   15.00    --  101.53 111.00  30.00  122
  8  ω     94.00 165.00   0.50   15.00    --  101.53  45.00 150.00  142
  9  ω     95.00 174.00   0.50   15.00    --  101.53  45.00 120.00  158
 10  ω     85.00 131.00   0.50   15.00    --  101.53  61.00  90.00   92
 11  ω     80.00 177.00   0.50   15.00    --  101.53  77.00  30.00  194
 12  ω     83.00 175.00   0.50   15.00    --  101.53  61.00-120.00  184
 13  ω     81.00 133.00   0.50   15.00    --  101.53  61.00 -90.00  104
 14  ω     75.00 178.00   0.50   15.00    --  101.53  77.00 -60.00  206
 15  ω     82.00 137.00   0.50   15.00    --  101.53  30.00  90.00  110
 16  ω     73.00 128.00   0.50   15.00    --  101.53 -77.00 120.00  110
 17  ω     75.00 110.00   0.50   15.00    --  101.53 -94.00  60.00   70
 18  ω     52.00  89.00   0.50   15.00    --  101.53 -94.00 -60.00   74
 19  ω     48.00  74.00   0.50   15.00    --  101.53 -75.00-136.00   52
 20  ω     92.00 121.00   0.50   15.00    --  101.53 -75.00-136.00   58
 21  ω     31.00  73.00   0.50    2.00    --   47.48 -75.00-136.00   84
 22  ω     27.00  87.00   0.50    2.00    --   47.48  57.00  90.00  120
 23  ω     65.00 149.00   0.50   15.00    --  101.53 178.00 150.00  168
 24  ω    -23.00   3.00   0.50    2.00    --  -47.48  75.00  -8.00   52
 25  ω    -62.00 -35.00   0.50    2.00    --  -47.48  75.00  -8.00   54
 26  ω    -89.00 -64.00   0.50   15.00    --  -90.25  75.00  -8.00   50
 27  ω    -87.00 -24.00   0.50   15.00    --  -90.25 111.00-120.00  126
 28  ω   -122.00 -27.00   0.50    2.00    --  -47.48 -57.00-180.00  190
 29  ω    -96.00 -71.00   0.50    2.00    --  -47.48 -75.00-136.00   50
 30  ω   -123.00 -71.00   0.50    2.00    --  -47.48-125.00 -90.00  104
 31  ω   -123.00 -78.00   0.50    2.00    --  -47.48-125.00-180.00   90
 32  ω   -139.00-114.00   0.50   15.00    --  -90.25 -75.00-136.00   50
 33  ω    -28.00  25.00   0.50    2.00    --   47.48 -75.00-136.00  106
 34  ω     31.00  96.00   0.50    2.00    --   47.48-125.00-150.00  130
 35  ω     36.00  96.00   0.50   15.00    --  101.53 -94.00 -30.00  120
 36  ω     44.00  93.00   0.50    2.00    --   47.48-125.00  60.00   98
 37  ω     32.00 102.00   0.50   15.00    --  101.53 -94.00 150.00  140
 38  ω     26.00  52.00   0.50   15.00    --  101.53 -77.00 120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0493459000
_diffrn_orient_matrix_UB_12      -0.0357538000
_diffrn_orient_matrix_UB_13      0.0585710000
_diffrn_orient_matrix_UB_21      0.0374603000
_diffrn_orient_matrix_UB_22      0.1132969000
_diffrn_orient_matrix_UB_23      -0.0018790000
_diffrn_orient_matrix_UB_31      -0.0305351000
_diffrn_orient_matrix_UB_32      0.0812181000
_diffrn_orient_matrix_UB_33      0.0284324000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            80297
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.738
_diffrn_reflns_theta_min         5.574
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       needle
_exptl_crystal_F_000             2656
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     821
_refine_ls_number_reflns         11351
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0428
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0658P)²+2.8171P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1162
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10012
_reflns_number_total             11351
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc00208a2.cif
_cod_data_source_block           tr235_0
_cod_depositor_comments
;Adding full bibliography for 7239983--7239986.cif.

 Adding full bibliography for 7239983--7239986.cif.
;
_cod_database_code               7239986
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C15H21NO6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.904
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C53A-O21A \\sim C53-O21
 with sigma of 0.005
 C52-O21A \\sim C52-O21
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(C53A) = Uanis(C53)
Uanis(O21A) = Uanis(O21)
4. Others
 Sof(O21)=Sof(C53)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-FVAR(1)
 Sof(O21A)=Sof(C53A)=Sof(H53A)=Sof(H53B)=Sof(H53C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C3(H3), C18(H18), C33(H33), C48(H48)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C49(H49A,H49B),
  C50(H50A,H50B), C51(H51A,H51B)
5.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C25(H25), C45(H45), C60(H60)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C), C42(H42A,H42B,H42C), C43(H43A,
 H43B,H43C), C46(H46A,H46B,H46C), C57(H57A,H57B,H57C), C58(H58A,H58B,H58C),
 C53A(H53A,H53B,H53C), C53(H53D,H53E,H53F)
5.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O12(H12), O18(H18A), O23(H23)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.496
_oxdiff_exptl_absorpt_empirical_full_min 0.796
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44141(5) 0.28192(11) 0.83755(5) 0.0293(3) Uani 1 1 d . . . . .
O2 O 0.37448(5) 0.17960(11) 0.85835(5) 0.0304(3) Uani 1 1 d . . . . .
O3 O 0.04772(5) 0.43600(13) 0.69430(5) 0.0357(3) Uani 1 1 d . . . . .
O4 O 0.05244(5) 0.33356(12) 0.62158(5) 0.0327(3) Uani 1 1 d . . . . .
O5 O 0.34166(4) 0.48528(10) 0.80596(4) 0.0197(2) Uani 1 1 d . . . . .
H5 H 0.309049 0.477956 0.806750 0.030 Uiso 1 1 calc GR . . . .
O6 O 0.35116(5) 0.67165(12) 0.67268(5) 0.0342(3) Uani 1 1 d . . . . .
N1 N 0.24360(5) 0.34248(13) 0.70995(5) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.48717(8) 0.2542(2) 0.89351(8) 0.0419(5) Uani 1 1 d . . . . .
H1A H 0.477502 0.294615 0.921134 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.525235 0.283891 0.897041 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.489191 0.165505 0.899557 0.063 Uiso 1 1 calc GR . . . .
C2 C 0.38661(7) 0.24098(14) 0.82613(6) 0.0217(3) Uani 1 1 d . . . . .
C3 C 0.34235(6) 0.27994(14) 0.76783(6) 0.0198(3) Uani 1 1 d . . . . .
H3 H 0.352228 0.237660 0.739843 0.024 Uiso 1 1 calc R . . . .
C4 C 0.27664(7) 0.25150(15) 0.75493(6) 0.0229(3) Uani 1 1 d . . . . .
H4A H 0.265891 0.166390 0.741740 0.028 Uiso 1 1 calc R . . . .
H4B H 0.269281 0.264895 0.787918 0.028 Uiso 1 1 calc R . . . .
C5 C 0.17934(7) 0.33219(17) 0.67427(7) 0.0272(3) Uani 1 1 d . . . . .
H5A H 0.168934 0.245249 0.664554 0.033 Uiso 1 1 calc R . . . .
H5B H 0.169122 0.378287 0.639497 0.033 Uiso 1 1 calc R . . . .
C6 C 0.14343(7) 0.38324(16) 0.70431(7) 0.0260(3) Uani 1 1 d . . . . .
H6A H 0.152447 0.334307 0.738131 0.031 Uiso 1 1 calc R . . . .
H6B H 0.155744 0.468647 0.715898 0.031 Uiso 1 1 calc R . . . .
C7 C 0.07683(7) 0.38051(15) 0.66777(7) 0.0252(3) Uani 1 1 d . . . . .
C8 C -0.01720(8) 0.4302(2) 0.66576(9) 0.0435(5) Uani 1 1 d . . . . .
H8A H -0.031200 0.473624 0.630327 0.065 Uiso 1 1 calc GR . . . .
H8B H -0.033629 0.468753 0.688968 0.065 Uiso 1 1 calc GR . . . .
H8C H -0.029759 0.344562 0.659092 0.065 Uiso 1 1 calc GR . . . .
C9 C 0.27876(6) 0.43502(14) 0.70838(6) 0.0193(3) Uani 1 1 d . . . . .
C10 C 0.34024(6) 0.42228(14) 0.75765(6) 0.0168(3) Uani 1 1 d . . . . .
C11 C 0.38131(6) 0.49343(14) 0.73697(6) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.43145(7) 0.56874(15) 0.78219(7) 0.0246(3) Uani 1 1 d . . . . .
H12A H 0.461782 0.512962 0.807096 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.415465 0.616549 0.803442 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.448712 0.624166 0.764527 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.40756(7) 0.40813(16) 0.70631(7) 0.0272(3) Uani 1 1 d . . . . .
H13A H 0.428486 0.457880 0.690178 0.041 Uiso 1 1 calc GR . . . .
H13B H 0.375684 0.363324 0.676824 0.041 Uiso 1 1 calc GR . . . .
H13C H 0.434920 0.349865 0.732748 0.041 Uiso 1 1 calc GR . . . .
C14 C 0.33487(7) 0.58061(15) 0.69162(6) 0.0226(3) Uani 1 1 d . . . . .
C15 C 0.27515(7) 0.53444(15) 0.67444(6) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.240393 0.566256 0.645557 0.027 Uiso 1 1 calc R . . . .
O7 O 0.11359(5) 0.35123(12) 0.45675(5) 0.0344(3) Uani 1 1 d . . . . .
O8 O 0.15284(5) 0.47846(11) 0.53147(4) 0.0251(2) Uani 1 1 d . . . . .
O9 O 0.43330(5) 0.39779(12) 0.48861(5) 0.0335(3) Uani 1 1 d . . . . .
O10 O 0.39267(10) 0.25912(15) 0.52465(9) 0.0682(5) Uani 1 1 d . . . . .
O11 O 0.24823(5) 0.34252(10) 0.31982(4) 0.0239(2) Uani 1 1 d . . . . .
O12 O 0.17354(4) 0.54489(9) 0.41520(4) 0.0189(2) Uani 1 1 d . . . . .
H12 H 0.171254 0.571373 0.385030 0.028 Uiso 1 1 calc GR . . . .
N2 N 0.30236(5) 0.52211(12) 0.50041(5) 0.0208(3) Uani 1 1 d . . . . .
C16 C 0.09370(7) 0.48290(17) 0.53079(7) 0.0297(4) Uani 1 1 d . . . . .
H16A H 0.064916 0.512398 0.494628 0.045 Uiso 1 1 calc GR . . . .
H16B H 0.094621 0.538502 0.559836 0.045 Uiso 1 1 calc GR . . . .
H16C H 0.082602 0.400738 0.537447 0.045 Uiso 1 1 calc GR . . . .
C17 C 0.15573(7) 0.40777(14) 0.49056(6) 0.0221(3) Uani 1 1 d . . . . .
C18 C 0.21714(7) 0.40632(14) 0.49118(6) 0.0203(3) Uani 1 1 d . . . . .
H18 H 0.233769 0.321900 0.500949 0.024 Uiso 1 1 calc R . . . .
C19 C 0.26420(7) 0.50035(15) 0.52998(6) 0.0221(3) Uani 1 1 d . . . . .
H19A H 0.245365 0.577191 0.533553 0.027 Uiso 1 1 calc R . . . .
H19B H 0.287311 0.465391 0.567300 0.027 Uiso 1 1 calc R . . . .
C20 C 0.36390(7) 0.56853(16) 0.52834(7) 0.0268(3) Uani 1 1 d . . . . .
H20A H 0.366018 0.634916 0.554282 0.032 Uiso 1 1 calc R . . . .
H20B H 0.375080 0.603419 0.500168 0.032 Uiso 1 1 calc R . . . .
C21 C 0.40840(8) 0.46591(19) 0.56086(7) 0.0343(4) Uani 1 1 d . . . . .
H21A H 0.448137 0.502121 0.579979 0.041 Uiso 1 1 calc R . . . .
H21B H 0.397596 0.432449 0.589526 0.041 Uiso 1 1 calc R . . . .
C22 C 0.41025(8) 0.36166(18) 0.52390(7) 0.0332(4) Uani 1 1 d . . . . .
C23 C 0.43428(10) 0.3043(2) 0.44926(8) 0.0476(5) Uani 1 1 d . . . . .
H23A H 0.461352 0.238485 0.469675 0.071 Uiso 1 1 calc GR . . . .
H23B H 0.447427 0.341793 0.423354 0.071 Uiso 1 1 calc GR . . . .
H23C H 0.394710 0.270704 0.428633 0.071 Uiso 1 1 calc GR . . . .
C24 C 0.27602(6) 0.48236(13) 0.44739(6) 0.0183(3) Uani 1 1 d . . . . .
C25 C 0.29180(6) 0.46593(14) 0.40386(6) 0.0202(3) Uani 1 1 d . . . . .
H25 H 0.324754 0.500847 0.400955 0.024 Uiso 1 1 calc R . . . .
C26 C 0.24824(6) 0.38535(14) 0.36396(6) 0.0188(3) Uani 1 1 d . . . . .
C27 C 0.20130(6) 0.34322(14) 0.38490(6) 0.0184(3) Uani 1 1 d . . . . .
C28 C 0.13761(7) 0.34272(15) 0.33770(6) 0.0230(3) Uani 1 1 d . . . . .
H28A H 0.135115 0.284765 0.308858 0.034 Uiso 1 1 calc GR . . . .
H28B H 0.127482 0.424929 0.321753 0.034 Uiso 1 1 calc GR . . . .
H28C H 0.110127 0.318150 0.352757 0.034 Uiso 1 1 calc GR . . . .
C29 C 0.21906(7) 0.21016(14) 0.40825(7) 0.0239(3) Uani 1 1 d . . . . .
H29A H 0.191273 0.180046 0.421964 0.036 Uiso 1 1 calc GR . . . .
H29B H 0.258762 0.211157 0.438635 0.036 Uiso 1 1 calc GR . . . .
H29C H 0.218236 0.156200 0.378719 0.036 Uiso 1 1 calc GR . . . .
C30 C 0.21261(6) 0.44004(13) 0.43246(6) 0.0170(3) Uani 1 1 d . . . . .
O13 O 0.36398(5) -0.01592(11) 0.51895(5) 0.0280(3) Uani 1 1 d . . . . .
O14 O 0.32488(5) -0.16458(11) 0.45320(5) 0.0276(3) Uani 1 1 d . . . . .
O15 O 0.06708(5) -0.02437(13) 0.51334(5) 0.0368(3) Uani 1 1 d . . . . .
O16 O 0.11857(7) 0.06770(14) 0.47135(7) 0.0504(4) Uani 1 1 d . . . . .
O17 O 0.25795(5) -0.00165(11) 0.67894(4) 0.0250(2) Uani 1 1 d . . . . .
O18 O 0.31545(4) -0.20961(10) 0.57388(4) 0.0193(2) Uani 1 1 d . . . . .
H18A H 0.320904 -0.232933 0.605495 0.029 Uiso 1 1 calc GR . . . .
N3 N 0.18424(5) -0.19252(12) 0.49781(5) 0.0197(3) Uani 1 1 d . . . . .
C31 C 0.41975(7) -0.02705(18) 0.51394(8) 0.0326(4) Uani 1 1 d . . . . .
H31A H 0.436112 -0.109096 0.525589 0.049 Uiso 1 1 calc GR . . . .
H31B H 0.447710 0.034235 0.537565 0.049 Uiso 1 1 calc GR . . . .
H31C H 0.412422 -0.013672 0.475326 0.049 Uiso 1 1 calc GR . . . .
C32 C 0.32059(7) -0.09261(14) 0.48664(6) 0.0195(3) Uani 1 1 d . . . . .
C33 C 0.26509(6) -0.07668(14) 0.49637(6) 0.0187(3) Uani 1 1 d . . . . .
H33 H 0.249951 0.008792 0.486556 0.022 Uiso 1 1 calc R . . . .
C34 C 0.21545(7) -0.16949(15) 0.46179(6) 0.0215(3) Uani 1 1 d . . . . .
H34A H 0.188377 -0.133765 0.425734 0.026 Uiso 1 1 calc R . . . .
H34B H 0.232264 -0.246145 0.455107 0.026 Uiso 1 1 calc R . . . .
C35 C 0.12285(7) -0.23782(15) 0.47541(7) 0.0243(3) Uani 1 1 d . . . . .
H35A H 0.114388 -0.265013 0.506444 0.029 Uiso 1 1 calc R . . . .
H35B H 0.118457 -0.309420 0.451287 0.029 Uiso 1 1 calc R . . . .
C36 C 0.07731(7) -0.13692(17) 0.44132(7) 0.0296(4) Uani 1 1 d . . . . .
H36A H 0.080361 -0.120907 0.406300 0.036 Uiso 1 1 calc R . . . .
H36B H 0.036956 -0.165835 0.431988 0.036 Uiso 1 1 calc R . . . .
C37 C 0.08943(7) -0.01878(17) 0.47532(7) 0.0324(4) Uani 1 1 d . . . . .
C38 C 0.08083(9) 0.0807(2) 0.55192(9) 0.0476(5) Uani 1 1 d . . . . .
H38A H 0.123193 0.096649 0.568516 0.071 Uiso 1 1 calc GR . . . .
H38B H 0.068711 0.061656 0.581168 0.071 Uiso 1 1 calc GR . . . .
H38C H 0.059669 0.153366 0.531564 0.071 Uiso 1 1 calc GR . . . .
C39 C 0.21473(6) -0.14655(13) 0.54940(6) 0.0178(3) Uani 1 1 d . . . . .
C40 C 0.27641(6) -0.10483(13) 0.55781(6) 0.0166(3) Uani 1 1 d . . . . .
C41 C 0.29272(6) -0.00497(14) 0.60497(6) 0.0182(3) Uani 1 1 d . . . . .
C42 C 0.35840(7) -0.00271(16) 0.64730(7) 0.0256(3) Uani 1 1 d . . . . .
H42A H 0.382467 0.021474 0.628472 0.038 Uiso 1 1 calc GR . . . .
H42B H 0.370268 -0.084351 0.663425 0.038 Uiso 1 1 calc GR . . . .
H42C H 0.363966 0.056185 0.676737 0.038 Uiso 1 1 calc GR . . . .
C43 C 0.27263(7) 0.12681(15) 0.58083(7) 0.0251(3) Uani 1 1 d . . . . .
H43A H 0.275877 0.182324 0.610734 0.038 Uiso 1 1 calc GR . . . .
H43B H 0.231730 0.124100 0.552728 0.038 Uiso 1 1 calc GR . . . .
H43C H 0.297756 0.156266 0.563948 0.038 Uiso 1 1 calc GR . . . .
C44 C 0.25135(6) -0.04530(14) 0.63258(6) 0.0191(3) Uani 1 1 d . . . . .
C45 C 0.20492(6) -0.12604(14) 0.59614(6) 0.0192(3) Uani 1 1 d . . . . .
H45 H 0.173787 -0.158677 0.602851 0.023 Uiso 1 1 calc R . . . .
O19 O 0.38085(4) 0.66342(10) 0.36084(4) 0.0234(2) Uani 1 1 d . . . . .
O20 O 0.45488(5) 0.57708(12) 0.34526(5) 0.0328(3) Uani 1 1 d . . . . .
O22 O 0.06485(5) 0.50379(13) 0.12176(5) 0.0344(3) Uani 1 1 d . . . . .
O23 O 0.35296(4) 0.35981(10) 0.31163(4) 0.0208(2) Uani 1 1 d . . . . .
H23 H 0.319562 0.363372 0.310953 0.031 Uiso 1 1 calc GR . . . .
O24 O 0.36369(5) 0.16400(12) 0.18303(5) 0.0328(3) Uani 1 1 d . . . . .
N4 N 0.25643(5) 0.50371(12) 0.21268(5) 0.0201(3) Uani 1 1 d . . . . .
C46 C 0.42521(7) 0.69782(17) 0.41692(7) 0.0281(3) Uani 1 1 d . . . . .
H46A H 0.441640 0.623647 0.438729 0.042 Uiso 1 1 calc GR . . . .
H46B H 0.406594 0.747778 0.435227 0.042 Uiso 1 1 calc GR . . . .
H46C H 0.456747 0.744783 0.413916 0.042 Uiso 1 1 calc GR . . . .
C47 C 0.40248(7) 0.60051(14) 0.32968(6) 0.0213(3) Uani 1 1 d . . . . .
C48 C 0.35476(6) 0.56392(14) 0.27242(6) 0.0189(3) Uani 1 1 d . . . . .
H48 H 0.364239 0.603258 0.243570 0.023 Uiso 1 1 calc R . . . .
C49 C 0.28885(6) 0.59377(14) 0.25863(6) 0.0212(3) Uani 1 1 d . . . . .
H49A H 0.280561 0.579433 0.291027 0.025 Uiso 1 1 calc R . . . .
H49B H 0.278683 0.679298 0.245864 0.025 Uiso 1 1 calc R . . . .
C50 C 0.19258(6) 0.51456(16) 0.17580(6) 0.0240(3) Uani 1 1 d . . . . .
H50A H 0.182583 0.464290 0.142168 0.029 Uiso 1 1 calc R . . . .
H50B H 0.182810 0.600834 0.164160 0.029 Uiso 1 1 calc R . . . .
C51 C 0.15616(7) 0.47087(18) 0.20645(7) 0.0294(4) Uani 1 1 d . . . . .
H51A H 0.170217 0.388893 0.222450 0.035 Uiso 1 1 calc R . . . .
H51B H 0.162980 0.527652 0.237439 0.035 Uiso 1 1 calc R . . . .
C52 C 0.09039(7) 0.46409(18) 0.16914(7) 0.0300(4) Uani 1 1 d D . . . .
C54 C 0.29098(6) 0.40796(14) 0.21348(6) 0.0180(3) Uani 1 1 d . . . . .
C55 C 0.35197(6) 0.42115(14) 0.26316(6) 0.0172(3) Uani 1 1 d . . . . .
C56 C 0.39320(6) 0.34937(15) 0.24315(6) 0.0205(3) Uani 1 1 d . . . . .
C57 C 0.44596(7) 0.28166(16) 0.28953(7) 0.0280(4) Uani 1 1 d . . . . .
H57A H 0.473694 0.341888 0.314261 0.042 Uiso 1 1 calc GR . . . .
H57B H 0.465829 0.230841 0.272704 0.042 Uiso 1 1 calc GR . . . .
H57C H 0.431517 0.229700 0.310778 0.042 Uiso 1 1 calc GR . . . .
C58 C 0.41599(7) 0.43336(17) 0.20913(7) 0.0278(4) Uani 1 1 d . . . . .
H58A H 0.443193 0.494435 0.233783 0.042 Uiso 1 1 calc GR . . . .
H58B H 0.382622 0.474889 0.179752 0.042 Uiso 1 1 calc GR . . . .
H58C H 0.436383 0.383224 0.192592 0.042 Uiso 1 1 calc GR . . . .
C59 C 0.34714(7) 0.25795(15) 0.19990(6) 0.0229(3) Uani 1 1 d . . . . .
C60 C 0.28745(6) 0.30476(15) 0.18143(6) 0.0214(3) Uani 1 1 d . . . . .
H60 H 0.252788 0.271363 0.153003 0.026 Uiso 1 1 calc R . . . .
O21A O 0.06283(12) 0.4010(9) 0.19575(16) 0.0441(12) Uani 0.86(3) 1 d D . P A 1
C53A C -0.0022(2) 0.4045(12) 0.1666(3) 0.0630(13) Uani 0.86(3) 1 d D . P A 1
H53A H -0.015836 0.350622 0.134230 0.094 Uiso 0.86(3) 1 calc GR . P A 1
H53B H -0.015187 0.488420 0.154683 0.094 Uiso 0.86(3) 1 calc GR . P A 1
H53C H -0.018635 0.376754 0.191782 0.094 Uiso 0.86(3) 1 calc GR . P A 1
O21 O 0.0604(7) 0.447(4) 0.2008(7) 0.0441(12) Uani 0.14(3) 1 d D . P A 2
C53 C -0.0013(14) 0.402(8) 0.177(2) 0.0630(13) Uani 0.14(3) 1 d D . P A 2
H53D H -0.013245 0.378027 0.138096 0.094 Uiso 0.14(3) 1 calc GR . P A 2
H53E H -0.027004 0.467871 0.178142 0.094 Uiso 0.14(3) 1 calc GR . P A 2
H53F H -0.004217 0.331734 0.197909 0.094 Uiso 0.14(3) 1 calc GR . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.74(13) . . ?
C7 O3 C8 115.98(14) . . ?
C10 O5 H5 109.5 . . ?
C5 N1 C4 122.41(13) . . ?
C9 N1 C4 111.95(12) . . ?
C9 N1 C5 125.57(13) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 111.04(13) . . ?
O2 C2 O1 124.11(14) . . ?
O2 C2 C3 124.85(14) . . ?
C2 C3 H3 109.1 . . ?
C2 C3 C4 113.69(12) . . ?
C2 C3 C10 113.88(12) . . ?
C4 C3 H3 109.1 . . ?
C4 C3 C10 101.76(11) . . ?
C10 C3 H3 109.1 . . ?
N1 C4 C3 102.18(12) . . ?
N1 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
N1 C5 C6 111.04(13) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.74(13) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
O3 C7 C6 110.32(14) . . ?
O4 C7 O3 124.11(14) . . ?
O4 C7 C6 125.55(15) . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C10 109.51(13) . . ?
N1 C9 C15 137.88(14) . . ?
C15 C9 C10 112.58(13) . . ?
O5 C10 C3 109.12(11) . . ?
O5 C10 C9 110.20(11) . . ?
O5 C10 C11 108.30(11) . . ?
C3 C10 C11 124.71(12) . . ?
C9 C10 C3 100.52(11) . . ?
C9 C10 C11 103.02(11) . . ?
C10 C11 C14 100.64(11) . . ?
C12 C11 C10 115.13(12) . . ?
C12 C11 C13 109.66(12) . . ?
C12 C11 C14 111.12(13) . . ?
C13 C11 C10 112.55(13) . . ?
C13 C11 C14 107.18(12) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O6 C14 C11 121.21(14) . . ?
O6 C14 C15 128.04(14) . . ?
C15 C14 C11 110.62(13) . . ?
C9 C15 C14 107.28(13) . . ?
C9 C15 H15 126.4 . . ?
C14 C15 H15 126.4 . . ?
C17 O8 C16 114.28(12) . . ?
C22 O9 C23 116.04(16) . . ?
C30 O12 H12 109.5 . . ?
C20 N2 C19 123.66(12) . . ?
C24 N2 C19 111.48(12) . . ?
C24 N2 C20 124.51(13) . . ?
O8 C16 H16A 109.5 . . ?
O8 C16 H16B 109.5 . . ?
O8 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O7 C17 O8 123.10(14) . . ?
O7 C17 C18 123.33(14) . . ?
O8 C17 C18 113.57(13) . . ?
C17 C18 H18 108.6 . . ?
C17 C18 C19 117.88(12) . . ?
C17 C18 C30 110.53(12) . . ?
C19 C18 H18 108.6 . . ?
C30 C18 H18 108.6 . . ?
C30 C18 C19 102.38(11) . . ?
N2 C19 C18 103.14(11) . . ?
N2 C19 H19A 111.1 . . ?
N2 C19 H19B 111.1 . . ?
C18 C19 H19A 111.1 . . ?
C18 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
N2 C20 H20A 109.2 . . ?
N2 C20 H20B 109.2 . . ?
N2 C20 C21 112.18(14) . . ?
H20A C20 H20B 107.9 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C20 C21 H21A 109.0 . . ?
C20 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 113.11(14) . . ?
C22 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
O9 C22 C21 112.12(17) . . ?
O10 C22 O9 123.33(18) . . ?
O10 C22 C21 124.54(18) . . ?
O9 C23 H23A 109.5 . . ?
O9 C23 H23B 109.5 . . ?
O9 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 C25 136.83(14) . . ?
N2 C24 C30 110.50(12) . . ?
C25 C24 C30 112.63(12) . . ?
C24 C25 H25 126.5 . . ?
C24 C25 C26 107.04(13) . . ?
C26 C25 H25 126.5 . . ?
O11 C26 C25 127.03(13) . . ?
O11 C26 C27 121.64(13) . . ?
C25 C26 C27 111.07(12) . . ?
C28 C27 C26 112.43(12) . . ?
C28 C27 C29 109.66(12) . . ?
C28 C27 C30 114.72(12) . . ?
C29 C27 C26 106.38(12) . . ?
C29 C27 C30 112.18(12) . . ?
C30 C27 C26 100.94(11) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O12 C30 C18 104.38(11) . . ?
O12 C30 C24 109.38(11) . . ?
O12 C30 C27 114.26(11) . . ?
C18 C30 C27 123.96(12) . . ?
C24 C30 C18 101.21(11) . . ?
C24 C30 C27 102.29(11) . . ?
C32 O13 C31 115.51(12) . . ?
C37 O15 C38 116.03(16) . . ?
C40 O18 H18A 109.5 . . ?
C35 N3 C34 122.76(12) . . ?
C39 N3 C34 111.59(12) . . ?
C39 N3 C35 124.63(12) . . ?
O13 C31 H31A 109.5 . . ?
O13 C31 H31B 109.5 . . ?
O13 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O13 C32 C33 111.42(12) . . ?
O14 C32 O13 123.94(13) . . ?
O14 C32 C33 124.63(14) . . ?
C32 C33 H33 109.4 . . ?
C32 C33 C34 112.33(12) . . ?
C32 C33 C40 112.88(12) . . ?
C34 C33 H33 109.4 . . ?
C34 C33 C40 103.16(11) . . ?
C40 C33 H33 109.4 . . ?
N3 C34 C33 103.65(11) . . ?
N3 C34 H34A 111.0 . . ?
N3 C34 H34B 111.0 . . ?
C33 C34 H34A 111.0 . . ?
C33 C34 H34B 111.0 . . ?
H34A C34 H34B 109.0 . . ?
N3 C35 H35A 109.2 . . ?
N3 C35 H35B 109.2 . . ?
N3 C35 C36 112.00(13) . . ?
H35A C35 H35B 107.9 . . ?
C36 C35 H35A 109.2 . . ?
C36 C35 H35B 109.2 . . ?
C35 C36 H36A 109.7 . . ?
C35 C36 H36B 109.7 . . ?
H36A C36 H36B 108.2 . . ?
C37 C36 C35 109.81(13) . . ?
C37 C36 H36A 109.7 . . ?
C37 C36 H36B 109.7 . . ?
O15 C37 C36 111.46(15) . . ?
O16 C37 O15 123.79(18) . . ?
O16 C37 C36 124.62(17) . . ?
O15 C38 H38A 109.5 . . ?
O15 C38 H38B 109.5 . . ?
O15 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
N3 C39 C40 110.45(12) . . ?
N3 C39 C45 137.06(14) . . ?
C45 C39 C40 112.49(13) . . ?
O18 C40 C33 104.86(11) . . ?
O18 C40 C39 108.88(11) . . ?
O18 C40 C41 113.55(11) . . ?
C33 C40 C41 124.51(12) . . ?
C39 C40 C33 101.04(11) . . ?
C39 C40 C41 102.51(11) . . ?
C42 C41 C40 114.83(12) . . ?
C42 C41 C43 109.79(13) . . ?
C42 C41 C44 112.09(12) . . ?
C43 C41 C40 112.19(12) . . ?
C43 C41 C44 106.70(12) . . ?
C44 C41 C40 100.69(11) . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
O17 C44 C41 121.25(13) . . ?
O17 C44 C45 127.53(13) . . ?
C45 C44 C41 111.02(12) . . ?
C39 C45 C44 107.14(12) . . ?
C39 C45 H45 126.4 . . ?
C44 C45 H45 126.4 . . ?
C47 O19 C46 114.90(11) . . ?
C55 O23 H23 109.5 . . ?
C50 N4 C49 122.57(12) . . ?
C54 N4 C49 111.85(12) . . ?
C54 N4 C50 125.24(13) . . ?
O19 C46 H46A 109.5 . . ?
O19 C46 H46B 109.5 . . ?
O19 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
O19 C47 C48 113.14(12) . . ?
O20 C47 O19 123.69(14) . . ?
O20 C47 C48 123.16(13) . . ?
C47 C48 H48 108.2 . . ?
C47 C48 C49 118.13(12) . . ?
C47 C48 C55 112.13(12) . . ?
C49 C48 H48 108.2 . . ?
C49 C48 C55 101.39(11) . . ?
C55 C48 H48 108.2 . . ?
N4 C49 C48 101.56(11) . . ?
N4 C49 H49A 111.5 . . ?
N4 C49 H49B 111.5 . . ?
C48 C49 H49A 111.5 . . ?
C48 C49 H49B 111.5 . . ?
H49A C49 H49B 109.3 . . ?
N4 C50 H50A 109.6 . . ?
N4 C50 H50B 109.6 . . ?
N4 C50 C51 110.19(12) . . ?
H50A C50 H50B 108.1 . . ?
C51 C50 H50A 109.6 . . ?
C51 C50 H50B 109.6 . . ?
C50 C51 H51A 108.9 . . ?
C50 C51 H51B 108.9 . . ?
H51A C51 H51B 107.7 . . ?
C52 C51 C50 113.31(14) . . ?
C52 C51 H51A 108.9 . . ?
C52 C51 H51B 108.9 . . ?
O22 C52 C51 126.54(16) . . ?
O22 C52 O21A 123.75(18) . . ?
O22 C52 O21 120.3(9) . . ?
O21A C52 C51 109.66(17) . . ?
O21 C52 C51 109.7(8) . . ?
N4 C54 C55 109.61(12) . . ?
N4 C54 C60 138.06(14) . . ?
C60 C54 C55 112.28(12) . . ?
O23 C55 C48 109.49(11) . . ?
O23 C55 C54 110.58(11) . . ?
O23 C55 C56 108.54(11) . . ?
C54 C55 C48 100.83(11) . . ?
C54 C55 C56 102.70(11) . . ?
C56 C55 C48 123.80(12) . . ?
C55 C56 C59 100.29(11) . . ?
C57 C56 C55 115.37(12) . . ?
C57 C56 C58 109.81(13) . . ?
C57 C56 C59 112.66(13) . . ?
C58 C56 C55 111.77(13) . . ?
C58 C56 C59 106.33(12) . . ?
C56 C57 H57A 109.5 . . ?
C56 C57 H57B 109.5 . . ?
C56 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C56 C58 H58A 109.5 . . ?
C56 C58 H58B 109.5 . . ?
C56 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
O24 C59 C56 121.36(13) . . ?
O24 C59 C60 128.06(14) . . ?
C60 C59 C56 110.41(13) . . ?
C54 C60 C59 107.05(13) . . ?
C54 C60 H60 126.5 . . ?
C59 C60 H60 126.5 . . ?
C52 O21A C53A 114.1(5) . . ?
O21A C53A H53A 109.5 . . ?
O21A C53A H53B 109.5 . . ?
O21A C53A H53C 109.5 . . ?
H53A C53A H53B 109.5 . . ?
H53A C53A H53C 109.5 . . ?
H53B C53A H53C 109.5 . . ?
C52 O21 C53 122(2) . . ?
O21 C53 H53D 109.5 . . ?
O21 C53 H53E 109.5 . . ?
O21 C53 H53F 109.5 . . ?
H53D C53 H53E 109.5 . . ?
H53D C53 H53F 109.5 . . ?
H53E C53 H53F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.444(2) . ?
O1 C2 1.3298(19) . ?
O2 C2 1.2075(19) . ?
O3 C7 1.339(2) . ?
O3 C8 1.450(2) . ?
O4 C7 1.205(2) . ?
O5 H5 0.8200 . ?
O5 C10 1.4236(17) . ?
O6 C14 1.239(2) . ?
N1 C4 1.474(2) . ?
N1 C5 1.4578(19) . ?
N1 C9 1.331(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.504(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.541(2) . ?
C3 C10 1.544(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.523(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.505(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.5161(19) . ?
C9 C15 1.366(2) . ?
C10 C11 1.5450(19) . ?
C11 C12 1.523(2) . ?
C11 C13 1.536(2) . ?
C11 C14 1.556(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.433(2) . ?
C15 H15 0.9300 . ?
O7 C17 1.199(2) . ?
O8 C16 1.4566(19) . ?
O8 C17 1.3410(18) . ?
O9 C22 1.339(2) . ?
O9 C23 1.446(2) . ?
O10 C22 1.184(3) . ?
O11 C26 1.2463(18) . ?
O12 H12 0.8200 . ?
O12 C30 1.4212(17) . ?
N2 C19 1.4781(19) . ?
N2 C20 1.461(2) . ?
N2 C24 1.3254(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.513(2) . ?
C18 H18 0.9800 . ?
C18 C19 1.542(2) . ?
C18 C30 1.5395(19) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.527(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.493(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.370(2) . ?
C24 C30 1.513(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.423(2) . ?
C26 C27 1.5523(19) . ?
C27 C28 1.525(2) . ?
C27 C29 1.538(2) . ?
C27 C30 1.552(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O13 C31 1.4472(19) . ?
O13 C32 1.3252(19) . ?
O14 C32 1.2072(19) . ?
O15 C37 1.336(2) . ?
O15 C38 1.452(2) . ?
O16 C37 1.206(2) . ?
O17 C44 1.2467(18) . ?
O18 H18A 0.8200 . ?
O18 C40 1.4199(17) . ?
N3 C34 1.4784(18) . ?
N3 C35 1.4539(19) . ?
N3 C39 1.3264(19) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 C33 1.5116(19) . ?
C33 H33 0.9800 . ?
C33 C34 1.534(2) . ?
C33 C40 1.5425(19) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.537(2) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.501(3) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.5119(19) . ?
C39 C45 1.368(2) . ?
C40 C41 1.551(2) . ?
C41 C42 1.520(2) . ?
C41 C43 1.538(2) . ?
C41 C44 1.5507(19) . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 0.9600 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.424(2) . ?
C45 H45 0.9300 . ?
O19 C46 1.4513(18) . ?
O19 C47 1.3377(18) . ?
O20 C47 1.2047(19) . ?
O22 C52 1.202(2) . ?
O23 H23 0.8200 . ?
O23 C55 1.4228(17) . ?
O24 C59 1.238(2) . ?
N4 C49 1.4794(19) . ?
N4 C50 1.4559(18) . ?
N4 C54 1.3293(19) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C48 1.506(2) . ?
C48 H48 0.9800 . ?
C48 C49 1.5431(19) . ?
C48 C55 1.545(2) . ?
C49 H49A 0.9700 . ?
C49 H49B 0.9700 . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
C50 C51 1.520(2) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
C51 C52 1.493(2) . ?
C52 O21A 1.351(3) . ?
C52 O21 1.347(5) . ?
C54 C55 1.5134(19) . ?
C54 C60 1.368(2) . ?
C55 C56 1.5406(19) . ?
C56 C57 1.527(2) . ?
C56 C58 1.537(2) . ?
C56 C59 1.557(2) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C59 C60 1.431(2) . ?
C60 H60 0.9300 . ?
O21A C53A 1.452(4) . ?
C53A H53A 0.9600 . ?
C53A H53B 0.9600 . ?
C53A H53C 0.9600 . ?
O21 C53 1.454(7) . ?
C53 H53D 0.9600 . ?
C53 H53E 0.9600 . ?
C53 H53F 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -171.97(13) . . . . ?
O1 C2 C3 C10 -56.02(17) . . . . ?
O2 C2 C3 C4 8.7(2) . . . . ?
O2 C2 C3 C10 124.68(16) . . . . ?
O5 C10 C11 C12 25.60(16) . . . . ?
O5 C10 C11 C13 152.26(12) . . . . ?
O5 C10 C11 C14 -93.94(12) . . . . ?
O6 C14 C15 C9 -178.05(16) . . . . ?
N1 C5 C6 C7 177.02(14) . . . . ?
N1 C9 C10 O5 -88.27(14) . . . . ?
N1 C9 C10 C3 26.77(15) . . . . ?
N1 C9 C10 C11 156.36(12) . . . . ?
N1 C9 C15 C14 -167.63(18) . . . . ?
C1 O1 C2 O2 -3.1(2) . . . . ?
C1 O1 C2 C3 177.55(14) . . . . ?
C2 C3 C4 N1 156.28(12) . . . . ?
C2 C3 C10 O5 -42.82(16) . . . . ?
C2 C3 C10 C9 -158.67(12) . . . . ?
C2 C3 C10 C11 87.29(17) . . . . ?
C3 C10 C11 C12 -104.84(16) . . . . ?
C3 C10 C11 C13 21.82(19) . . . . ?
C3 C10 C11 C14 135.62(14) . . . . ?
C4 N1 C5 C6 80.89(18) . . . . ?
C4 N1 C9 C10 -5.59(17) . . . . ?
C4 N1 C9 C15 172.35(18) . . . . ?
C4 C3 C10 O5 79.93(13) . . . . ?
C4 C3 C10 C9 -35.92(13) . . . . ?
C4 C3 C10 C11 -149.96(13) . . . . ?
C5 N1 C4 C3 164.67(13) . . . . ?
C5 N1 C9 C10 171.39(13) . . . . ?
C5 N1 C9 C15 -10.7(3) . . . . ?
C5 C6 C7 O3 -174.71(14) . . . . ?
C5 C6 C7 O4 6.5(2) . . . . ?
C8 O3 C7 O4 4.0(2) . . . . ?
C8 O3 C7 C6 -174.82(15) . . . . ?
C9 N1 C4 C3 -18.24(16) . . . . ?
C9 N1 C5 C6 -95.78(18) . . . . ?
C9 C10 C11 C12 142.32(13) . . . . ?
C9 C10 C11 C13 -91.02(14) . . . . ?
C9 C10 C11 C14 22.78(14) . . . . ?
C10 C3 C4 N1 33.39(14) . . . . ?
C10 C9 C15 C14 10.27(17) . . . . ?
C10 C11 C14 O6 165.00(15) . . . . ?
C10 C11 C14 C15 -18.86(15) . . . . ?
C11 C14 C15 C9 6.14(17) . . . . ?
C12 C11 C14 O6 42.61(19) . . . . ?
C12 C11 C14 C15 -141.26(13) . . . . ?
C13 C11 C14 O6 -77.19(18) . . . . ?
C13 C11 C14 C15 98.95(14) . . . . ?
C15 C9 C10 O5 93.23(14) . . . . ?
C15 C9 C10 C3 -151.73(13) . . . . ?
C15 C9 C10 C11 -22.14(16) . . . . ?
O7 C17 C18 C19 169.58(15) . . . . ?
O7 C17 C18 C30 52.4(2) . . . . ?
O8 C17 C18 C19 -10.39(19) . . . . ?
O8 C17 C18 C30 -127.59(13) . . . . ?
O11 C26 C27 C28 -46.67(19) . . . . ?
O11 C26 C27 C29 73.39(17) . . . . ?
O11 C26 C27 C30 -169.38(13) . . . . ?
N2 C20 C21 C22 61.28(19) . . . . ?
N2 C24 C25 C26 162.73(17) . . . . ?
N2 C24 C30 O12 84.90(14) . . . . ?
N2 C24 C30 C18 -24.86(15) . . . . ?
N2 C24 C30 C27 -153.61(12) . . . . ?
C16 O8 C17 O7 -1.1(2) . . . . ?
C16 O8 C17 C18 178.83(13) . . . . ?
C17 C18 C19 N2 -151.17(13) . . . . ?
C17 C18 C30 O12 45.15(15) . . . . ?
C17 C18 C30 C24 158.72(12) . . . . ?
C17 C18 C30 C27 -88.01(16) . . . . ?
C19 N2 C20 C21 79.05(18) . . . . ?
C19 N2 C24 C25 -171.20(17) . . . . ?
C19 N2 C24 C30 6.02(17) . . . . ?
C19 C18 C30 O12 -81.25(13) . . . . ?
C19 C18 C30 C24 32.33(14) . . . . ?
C19 C18 C30 C27 145.60(13) . . . . ?
C20 N2 C19 C18 -158.00(14) . . . . ?
C20 N2 C24 C25 2.3(3) . . . . ?
C20 N2 C24 C30 179.52(13) . . . . ?
C20 C21 C22 O9 67.78(19) . . . . ?
C20 C21 C22 O10 -111.1(2) . . . . ?
C23 O9 C22 O10 1.7(3) . . . . ?
C23 O9 C22 C21 -177.20(14) . . . . ?
C24 N2 C19 C18 15.56(16) . . . . ?
C24 N2 C20 C21 -93.68(18) . . . . ?
C24 C25 C26 O11 -176.03(14) . . . . ?
C24 C25 C26 C27 -1.89(17) . . . . ?
C25 C24 C30 O12 -97.16(14) . . . . ?
C25 C24 C30 C18 153.08(13) . . . . ?
C25 C24 C30 C27 24.33(16) . . . . ?
C25 C26 C27 C28 138.83(13) . . . . ?
C25 C26 C27 C29 -101.12(14) . . . . ?
C25 C26 C27 C30 16.11(15) . . . . ?
C26 C27 C30 O12 95.75(13) . . . . ?
C26 C27 C30 C18 -135.07(13) . . . . ?
C26 C27 C30 C24 -22.33(13) . . . . ?
C28 C27 C30 O12 -25.37(17) . . . . ?
C28 C27 C30 C18 103.82(16) . . . . ?
C28 C27 C30 C24 -143.44(12) . . . . ?
C29 C27 C30 O12 -151.36(12) . . . . ?
C29 C27 C30 C18 -22.17(19) . . . . ?
C29 C27 C30 C24 90.57(13) . . . . ?
C30 C18 C19 N2 -29.69(14) . . . . ?
C30 C24 C25 C26 -14.45(17) . . . . ?
O13 C32 C33 C34 -176.87(12) . . . . ?
O13 C32 C33 C40 -60.73(16) . . . . ?
O14 C32 C33 C34 4.1(2) . . . . ?
O14 C32 C33 C40 120.24(16) . . . . ?
O17 C44 C45 C39 178.15(15) . . . . ?
O18 C40 C41 C42 26.21(17) . . . . ?
O18 C40 C41 C43 152.48(12) . . . . ?
O18 C40 C41 C44 -94.40(13) . . . . ?
N3 C35 C36 C37 -50.70(18) . . . . ?
N3 C39 C40 O18 -84.13(14) . . . . ?
N3 C39 C40 C33 25.92(15) . . . . ?
N3 C39 C40 C41 155.31(12) . . . . ?
N3 C39 C45 C44 -165.76(17) . . . . ?
C31 O13 C32 O14 -2.8(2) . . . . ?
C31 O13 C32 C33 178.12(13) . . . . ?
C32 C33 C34 N3 148.31(12) . . . . ?
C32 C33 C40 O18 -39.26(15) . . . . ?
C32 C33 C40 C39 -152.39(12) . . . . ?
C32 C33 C40 C41 93.90(16) . . . . ?
C33 C40 C41 C42 -103.52(16) . . . . ?
C33 C40 C41 C43 22.75(18) . . . . ?
C33 C40 C41 C44 135.88(13) . . . . ?
C34 N3 C35 C36 -72.24(18) . . . . ?
C34 N3 C39 C40 -9.58(16) . . . . ?
C34 N3 C39 C45 169.54(17) . . . . ?
C34 C33 C40 O18 82.23(13) . . . . ?
C34 C33 C40 C39 -30.91(13) . . . . ?
C34 C33 C40 C41 -144.62(13) . . . . ?
C35 N3 C34 C33 157.64(13) . . . . ?
C35 N3 C39 C40 -178.26(13) . . . . ?
C35 N3 C39 C45 0.9(3) . . . . ?
C35 C36 C37 O15 -79.88(17) . . . . ?
C35 C36 C37 O16 96.1(2) . . . . ?
C38 O15 C37 O16 -1.3(2) . . . . ?
C38 O15 C37 C36 174.79(14) . . . . ?
C39 N3 C34 C33 -11.28(16) . . . . ?
C39 N3 C35 C36 95.22(17) . . . . ?
C39 C40 C41 C42 143.49(13) . . . . ?
C39 C40 C41 C43 -90.24(13) . . . . ?
C39 C40 C41 C44 22.88(13) . . . . ?
C40 C33 C34 N3 26.45(14) . . . . ?
C40 C39 C45 C44 13.35(17) . . . . ?
C40 C41 C44 O17 167.51(13) . . . . ?
C40 C41 C44 C45 -17.30(15) . . . . ?
C41 C44 C45 C39 3.33(17) . . . . ?
C42 C41 C44 O17 44.97(19) . . . . ?
C42 C41 C44 C45 -139.84(13) . . . . ?
C43 C41 C44 O17 -75.24(17) . . . . ?
C43 C41 C44 C45 99.95(14) . . . . ?
C45 C39 C40 O18 96.51(14) . . . . ?
C45 C39 C40 C33 -153.43(12) . . . . ?
C45 C39 C40 C41 -24.05(15) . . . . ?
O19 C47 C48 C49 -4.09(19) . . . . ?
O19 C47 C48 C55 -121.42(13) . . . . ?
O20 C47 C48 C49 177.09(15) . . . . ?
O20 C47 C48 C55 59.8(2) . . . . ?
O22 C52 O21A C53A -10.9(10) . . . . ?
O22 C52 O21 C53 37(6) . . . . ?
O23 C55 C56 C57 -29.54(17) . . . . ?
O23 C55 C56 C58 -155.91(12) . . . . ?
O23 C55 C56 C59 91.75(13) . . . . ?
O24 C59 C60 C54 177.93(16) . . . . ?
N4 C50 C51 C52 -172.78(14) . . . . ?
N4 C54 C55 O23 90.87(14) . . . . ?
N4 C54 C55 C48 -24.90(14) . . . . ?
N4 C54 C55 C56 -153.49(12) . . . . ?
N4 C54 C60 C59 165.98(17) . . . . ?
C46 O19 C47 O20 -2.6(2) . . . . ?
C46 O19 C47 C48 178.56(13) . . . . ?
C47 C48 C49 N4 -158.18(13) . . . . ?
C47 C48 C55 O23 46.56(15) . . . . ?
C47 C48 C55 C54 163.13(11) . . . . ?
C47 C48 C55 C56 -83.45(16) . . . . ?
C48 C55 C56 C57 100.86(17) . . . . ?
C48 C55 C56 C58 -25.52(19) . . . . ?
C48 C55 C56 C59 -137.86(13) . . . . ?
C49 N4 C50 C51 -76.79(18) . . . . ?
C49 N4 C54 C55 2.14(16) . . . . ?
C49 N4 C54 C60 -175.21(17) . . . . ?
C49 C48 C55 O23 -80.39(13) . . . . ?
C49 C48 C55 C54 36.18(13) . . . . ?
C49 C48 C55 C56 149.60(13) . . . . ?
C50 N4 C49 C48 -164.67(13) . . . . ?
C50 N4 C54 C55 -171.34(13) . . . . ?
C50 N4 C54 C60 11.3(3) . . . . ?
C50 C51 C52 O22 -10.1(3) . . . . ?
C50 C51 C52 O21A 167.4(5) . . . . ?
C50 C51 C52 O21 -169.2(19) . . . . ?
C51 C52 O21A C53A 171.5(6) . . . . ?
C51 C52 O21 C53 -163(5) . . . . ?
C54 N4 C49 C48 21.65(15) . . . . ?
C54 N4 C50 C51 96.03(17) . . . . ?
C54 C55 C56 C57 -146.64(13) . . . . ?
C54 C55 C56 C58 86.98(14) . . . . ?
C54 C55 C56 C59 -25.36(14) . . . . ?
C55 C48 C49 N4 -35.26(13) . . . . ?
C55 C54 C60 C59 -11.32(17) . . . . ?
C55 C56 C59 O24 -163.41(15) . . . . ?
C55 C56 C59 C60 21.04(15) . . . . ?
C56 C59 C60 C54 -6.89(17) . . . . ?
C57 C56 C59 O24 -40.2(2) . . . . ?
C57 C56 C59 C60 144.24(13) . . . . ?
C58 C56 C59 O24 80.11(18) . . . . ?
C58 C56 C59 C60 -95.44(14) . . . . ?
C60 C54 C55 O23 -91.05(14) . . . . ?
C60 C54 C55 C48 153.18(12) . . . . ?
C60 C54 C55 C56 24.59(16) . . . . ?
