#------------------------------------------------------------------------------
#$Date: 2022-10-29 13:56:09 +0300 (Sat, 29 Oct 2022) $
#$Revision: 278870 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158956.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_7158956
loop_
_publ_author_name
'Li, Min'
'Chen, Yihua'
'Yan, Yinkun'
'Liu, Min'
'Huang, Min'
'Li, Wenzhe'
'Cao, Lianyi'
'Zhang, Xiao-Mei'
_publ_section_title
;
 Organocatalytic asymmetric synthesis of quaternary
 α-isoxazole-α-alkynylamino acid derivatives
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01746F
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H31 N3 O5'
_chemical_formula_sum            'C28 H31 N3 O5'
_chemical_formula_weight         489.56
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2020-12-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-28 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5012(5)
_cell_length_b                   17.0320(7)
_cell_length_c                   18.9074(10)
_cell_measurement_reflns_used    2869
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.6570
_cell_measurement_theta_min      5.1770
_cell_volume                     2737.6(2)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -26.00   1.00    2.00    --  -33.50 -77.00  90.00   76
  2  ω    -62.00   1.00   1.00    2.00    --  -33.50  77.00-180.00   63
  3  ω    -82.00 -32.00   1.00    2.00    --  -33.50 178.00 120.00   50
  4  ω     70.00 105.00   1.00    2.00    --   36.47 178.00  30.00   35
  5  ω     58.00 110.00   1.00    2.00    --   36.47 178.00-180.00   52
  6  ω     42.00  67.00   1.00    2.00    --   36.47 -99.00  90.00   25
  7  ω     32.00  58.00   1.00    2.00    --   36.47  57.00-150.00   26
  8  ω     74.00 101.00   1.00    2.00    --   36.47  57.00-150.00   27
  9  ω     12.00  38.00   1.00    2.00    --   36.47 -99.00  90.00   26
 10  ω     81.00 107.00   1.00    2.00    --   36.47 178.00 -60.00   26
 11  ω     42.00  68.00   1.00   13.00    --  108.00 -94.00  90.00   26
 12  ω    112.00 177.00   1.00   13.00    --  108.00 111.00 -60.00   65
 13  ω     38.00 110.00   1.00   13.00    --  108.00 -94.00   0.00   72
 14  ω     49.00 102.00   1.00   13.00    --  108.00 -61.00  60.00   53
 15  ω    122.00 178.00   1.00   13.00    --  108.00 111.00  60.00   56
 16  ω     50.00 132.00   1.00   13.00    --  108.00 -30.00 120.00   82
 17  ω     72.00 100.00   1.00   13.00    --  108.00 -94.00 150.00   28
 18  ω     63.00  89.00   1.00   13.00    --  108.00 -95.00 -85.00   26
 19  ω     51.00 128.00   1.00   13.00    --  108.00 -30.00 -30.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1448656000
_diffrn_orient_matrix_UB_12      -0.0189623000
_diffrn_orient_matrix_UB_13      -0.0458578000
_diffrn_orient_matrix_UB_21      0.0860251000
_diffrn_orient_matrix_UB_22      0.0319446000
_diffrn_orient_matrix_UB_23      -0.0656952000
_diffrn_orient_matrix_UB_31      0.0666950000
_diffrn_orient_matrix_UB_32      -0.0824656000
_diffrn_orient_matrix_UB_33      -0.0148900000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10617
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.777
_diffrn_reflns_theta_min         3.493
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77583
_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_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(17)
_refine_ls_extinction_coef       0.0028(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0604P)²+0.1837P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1393
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3979
_reflns_number_total             5157
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01746f2.cif
_cod_data_source_block           202012316
_cod_original_cell_volume        2737.7(2)
_cod_database_code               7158956
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N4
_chemical_oxdiff_usercomment     r
_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   0.936
_shelx_estimated_absorpt_t_min   0.895
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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
2. Restrained distances
 C19A-C20A
 1.55 with sigma of 0.02
 H2A-N2
 0.87 with sigma of 0.02
 N3-H3A
 0.87 with sigma of 0.02
 C22-C23
 1.65 with sigma of 0.02
 C22A-C23A
 1.65 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
4. Others
 Sof(C22A)=Sof(H22C)=Sof(H22D)=Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=FVAR(1)
 Sof(C19A)=Sof(H19C)=Sof(H19D)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(2)
 Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C19A(H19C,H19D), C22(H22A,H22B), C22A(H22C,H22D)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
5.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C20A(H20D,H20E,H20F), C23(H23A,H23B,H23C), C23A(H23D,
 H23E,H23F), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.841
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
C1 C 0.6033(6) 0.4838(2) 0.0584(2) 0.0718(10) Uani 1 1 d . . . . .
H1 H 0.5526 0.5041 0.0980 0.086 Uiso 1 1 calc R . . . .
C2 C 0.6763(7) 0.5338(3) 0.0108(2) 0.0876(14) Uani 1 1 d . . . . .
H2 H 0.6752 0.5877 0.0189 0.105 Uiso 1 1 calc R . . . .
C3 C 0.7506(7) 0.5042(3) -0.0483(2) 0.0908(14) Uani 1 1 d . . . . .
H3 H 0.7991 0.5381 -0.0802 0.109 Uiso 1 1 calc R . . . .
C4 C 0.7527(6) 0.4251(3) -0.0600(2) 0.0816(12) Uani 1 1 d . . . . .
H4 H 0.8030 0.4052 -0.0998 0.098 Uiso 1 1 calc R . . . .
C5 C 0.6805(5) 0.3746(2) -0.0130(2) 0.0708(10) Uani 1 1 d . . . . .
H5 H 0.6819 0.3208 -0.0215 0.085 Uiso 1 1 calc R . . . .
C6 C 0.6059(4) 0.4035(2) 0.04698(18) 0.0594(8) Uani 1 1 d . . . . .
C7 C 0.5281(4) 0.3500(2) 0.09713(19) 0.0580(8) Uani 1 1 d . . . . .
C8 C 0.5297(4) 0.34944(19) 0.17256(18) 0.0548(7) Uani 1 1 d . . . . .
C9 C 0.4330(4) 0.28831(19) 0.1894(2) 0.0620(8) Uani 1 1 d . . . . .
C10 C 0.6290(4) 0.39780(18) 0.22317(17) 0.0539(7) Uani 1 1 d . . . . .
C11 C 0.6803(5) 0.3483(2) 0.28383(19) 0.0631(9) Uani 1 1 d . . . . .
C12 C 0.7326(5) 0.3060(2) 0.32739(19) 0.0679(9) Uani 1 1 d . . . . .
C13 C 0.7923(6) 0.2524(3) 0.3800(2) 0.0771(11) Uani 1 1 d . . . . .
C14 C 0.9063(7) 0.2766(4) 0.4271(3) 0.0993(16) Uani 1 1 d . . . . .
H14 H 0.9463 0.3274 0.4246 0.119 Uiso 1 1 calc R . . . .
C15 C 0.9614(10) 0.2243(5) 0.4785(4) 0.132(3) Uani 1 1 d . . . . .
H15 H 1.0380 0.2401 0.5106 0.158 Uiso 1 1 calc R . . . .
C16 C 0.9031(10) 0.1510(6) 0.4813(5) 0.158(4) Uani 1 1 d . . . . .
H16 H 0.9389 0.1167 0.5160 0.190 Uiso 1 1 calc R . . . .
C17 C 0.7941(10) 0.1263(5) 0.4350(5) 0.150(3) Uani 1 1 d . . . . .
H17 H 0.7560 0.0752 0.4377 0.180 Uiso 1 1 calc R . . . .
C18 C 0.7381(8) 0.1765(3) 0.3833(4) 0.1125(19) Uani 1 1 d . . . . .
H18 H 0.6640 0.1589 0.3507 0.135 Uiso 1 1 calc R . . . .
C19 C 0.2672(12) 0.1965(7) 0.2562(7) 0.092(3) Uani 0.807(12) 1 d . . P A 1
H19A H 0.3037 0.1499 0.2317 0.110 Uiso 0.807(12) 1 calc R . P A 1
H19B H 0.1707 0.2139 0.2337 0.110 Uiso 0.807(12) 1 calc R . P A 1
C19A C 0.316(5) 0.186(3) 0.267(4) 0.092(3) Uani 0.193(12) 1 d D . P A 2
H19C H 0.3699 0.1610 0.3063 0.110 Uiso 0.193(12) 1 calc R . P A 2
H19D H 0.3173 0.1518 0.2267 0.110 Uiso 0.193(12) 1 calc R . P A 2
C20 C 0.2362(14) 0.1775(5) 0.3315(5) 0.133(4) Uani 0.807(12) 1 d . . P A 1
H20A H 0.2034 0.2241 0.3559 0.200 Uiso 0.807(12) 1 calc GR . P A 1
H20B H 0.3304 0.1574 0.3529 0.200 Uiso 0.807(12) 1 calc GR . P A 1
H20C H 0.1546 0.1386 0.3344 0.200 Uiso 0.807(12) 1 calc GR . P A 1
C20A C 0.146(5) 0.208(2) 0.288(2) 0.133(4) Uani 0.193(12) 1 d D . P A 2
H20D H 0.1468 0.2382 0.3310 0.200 Uiso 0.193(12) 1 calc GR . P A 2
H20E H 0.0856 0.1612 0.2949 0.200 Uiso 0.193(12) 1 calc GR . P A 2
H20F H 0.0991 0.2389 0.2510 0.200 Uiso 0.193(12) 1 calc GR . P A 2
C21 C 0.7866(4) 0.4249(2) 0.1894(2) 0.0627(9) Uani 1 1 d . . . . .
C22 C 1.0016(11) 0.3949(6) 0.1195(6) 0.087(2) Uani 0.571(7) 1 d D . P B 1
H22A H 0.9738 0.4379 0.0883 0.105 Uiso 0.571(7) 1 calc R . P B 1
H22B H 1.0834 0.4122 0.1516 0.105 Uiso 0.571(7) 1 calc R . P B 1
C22A C 1.0331(15) 0.3637(8) 0.1488(7) 0.087(2) Uani 0.429(7) 1 d D . P B 2
H22C H 1.0735 0.3108 0.1539 0.105 Uiso 0.429(7) 1 calc R . P B 2
H22D H 1.0866 0.3979 0.1821 0.105 Uiso 0.429(7) 1 calc R . P B 2
C23 C 1.0532(15) 0.3254(7) 0.0785(6) 0.123(3) Uani 0.571(7) 1 d D . P B 1
H23A H 1.0529 0.2800 0.1086 0.184 Uiso 0.571(7) 1 calc GR . P B 1
H23B H 1.1576 0.3341 0.0608 0.184 Uiso 0.571(7) 1 calc GR . P B 1
H23C H 0.9826 0.3171 0.0396 0.184 Uiso 0.571(7) 1 calc GR . P B 1
C23A C 1.052(2) 0.3928(11) 0.0742(8) 0.123(3) Uani 0.429(7) 1 d D . P B 2
H23D H 1.1578 0.4105 0.0672 0.184 Uiso 0.429(7) 1 calc GR . P B 2
H23E H 0.9804 0.4355 0.0661 0.184 Uiso 0.429(7) 1 calc GR . P B 2
H23F H 1.0291 0.3509 0.0418 0.184 Uiso 0.429(7) 1 calc GR . P B 2
C24 C 0.4260(5) 0.4716(2) 0.28937(19) 0.0611(8) Uani 1 1 d . . . . .
C25 C 0.2479(5) 0.5653(2) 0.3468(2) 0.0684(9) Uani 1 1 d . . . . .
C26 C 0.2526(8) 0.5281(3) 0.4187(3) 0.1028(16) Uani 1 1 d . . . . .
H26A H 0.2394 0.4724 0.4142 0.154 Uiso 1 1 calc GR . . . .
H26B H 0.1694 0.5491 0.4473 0.154 Uiso 1 1 calc GR . . . .
H26C H 0.3521 0.5390 0.4407 0.154 Uiso 1 1 calc GR . . . .
C27 C 0.1052(6) 0.5398(4) 0.3051(4) 0.1157(19) Uani 1 1 d . . . . .
H27A H 0.1086 0.5629 0.2588 0.174 Uiso 1 1 calc GR . . . .
H27B H 0.0115 0.5566 0.3290 0.174 Uiso 1 1 calc GR . . . .
H27C H 0.1047 0.4836 0.3009 0.174 Uiso 1 1 calc GR . . . .
C28 C 0.2591(8) 0.6542(3) 0.3527(4) 0.117(2) Uani 1 1 d . . . . .
H28A H 0.3497 0.6680 0.3803 0.176 Uiso 1 1 calc GR . . . .
H28B H 0.1661 0.6741 0.3752 0.176 Uiso 1 1 calc GR . . . .
H28C H 0.2685 0.6765 0.3062 0.176 Uiso 1 1 calc GR . . . .
N1 N 0.4409(4) 0.2935(2) 0.07079(18) 0.0754(9) Uani 1 1 d . . . . .
N2 N 0.3853(5) 0.2578(2) 0.2514(2) 0.0818(10) Uani 1 1 d D . . . .
H2A H 0.396(5) 0.289(2) 0.2861(16) 0.062(11) Uiso 1 1 d D . . . .
N3 N 0.5535(4) 0.47010(17) 0.24687(17) 0.0622(7) Uani 1 1 d D . . . .
H3A H 0.606(5) 0.5129(18) 0.241(2) 0.077(13) Uiso 1 1 d D . . . .
O1 O 0.3786(3) 0.25319(15) 0.13083(16) 0.0762(8) Uani 1 1 d . . . . .
O2 O 0.8327(4) 0.49092(18) 0.19390(19) 0.0882(9) Uani 1 1 d . . . . .
O3 O 0.8599(3) 0.36596(18) 0.15953(16) 0.0792(8) Uani 1 1 d . . . . .
O4 O 0.3553(4) 0.41389(14) 0.30881(19) 0.0884(10) Uani 1 1 d . . . . .
O5 O 0.3913(3) 0.54609(13) 0.30597(15) 0.0694(7) Uani 1 1 d . . . . .
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 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 119.9(4) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.3(4) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.5(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 C7 120.3(3) . . ?
C5 C6 C7 120.7(3) . . ?
C8 C7 C6 130.1(3) . . ?
N1 C7 C6 117.6(3) . . ?
N1 C7 C8 112.3(3) . . ?
C7 C8 C10 129.2(3) . . ?
C9 C8 C7 103.5(3) . . ?
C9 C8 C10 127.0(3) . . ?
N2 C9 C8 132.9(4) . . ?
O1 C9 C8 110.8(3) . . ?
O1 C9 N2 116.3(3) . . ?
C8 C10 C21 112.4(3) . . ?
C11 C10 C8 109.9(3) . . ?
C11 C10 C21 103.4(3) . . ?
N3 C10 C8 114.0(3) . . ?
N3 C10 C11 111.8(3) . . ?
N3 C10 C21 104.8(3) . . ?
C12 C11 C10 173.2(4) . . ?
C11 C12 C13 178.1(5) . . ?
C14 C13 C12 120.2(5) . . ?
C18 C13 C12 120.5(5) . . ?
C18 C13 C14 119.3(5) . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.5(6) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.7(7) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(7) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.4(8) . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.8(7) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
H19A C19 H19B 108.2 . . ?
C20 C19 H19A 109.7 . . ?
C20 C19 H19B 109.7 . . ?
N2 C19 H19A 109.7 . . ?
N2 C19 H19B 109.7 . . ?
N2 C19 C20 109.8(9) . . ?
H19C C19A H19D 109.0 . . ?
C20A C19A H19C 110.9 . . ?
C20A C19A H19D 110.9 . . ?
N2 C19A H19C 110.9 . . ?
N2 C19A H19D 110.9 . . ?
N2 C19A C20A 104(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O2 C21 C10 122.2(3) . . ?
O2 C21 O3 126.6(4) . . ?
O3 C21 C10 111.1(3) . . ?
H22A C22 H22B 109.0 . . ?
C23 C22 H22A 111.0 . . ?
C23 C22 H22B 111.0 . . ?
C23 C22 O3 103.8(8) . . ?
O3 C22 H22A 111.0 . . ?
O3 C22 H22B 111.0 . . ?
H22C C22A H22D 109.1 . . ?
C23A C22A H22C 111.2 . . ?
C23A C22A H22D 111.2 . . ?
O3 C22A H22C 111.2 . . ?
O3 C22A H22D 111.2 . . ?
O3 C22A C23A 103.0(11) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22A C23A H23D 109.5 . . ?
C22A C23A H23E 109.5 . . ?
C22A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
O4 C24 N3 124.4(3) . . ?
O4 C24 O5 126.1(3) . . ?
O5 C24 N3 109.5(3) . . ?
C26 C25 C27 111.9(5) . . ?
C26 C25 C28 110.6(4) . . ?
C27 C25 C28 112.0(5) . . ?
O5 C25 C26 110.9(4) . . ?
O5 C25 C27 109.0(3) . . ?
O5 C25 C28 102.0(4) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C7 N1 O1 105.1(3) . . ?
C9 N2 C19 122.8(6) . . ?
C9 N2 C19A 131(3) . . ?
C9 N2 H2A 114(3) . . ?
C19 N2 H2A 118(3) . . ?
C19A N2 H2A 115(4) . . ?
C10 N3 H3A 116(3) . . ?
C24 N3 C10 123.5(3) . . ?
C24 N3 H3A 118(3) . . ?
C9 O1 N1 108.3(3) . . ?
C21 O3 C22 110.3(5) . . ?
C21 O3 C22A 123.4(6) . . ?
C24 O5 C25 120.9(3) . . ?
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
C1 H1 0.9300 . ?
C1 C2 1.386(6) . ?
C1 C6 1.383(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.365(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(5) . ?
C6 C7 1.473(5) . ?
C7 C8 1.426(5) . ?
C7 N1 1.312(5) . ?
C8 C9 1.364(5) . ?
C8 C10 1.518(5) . ?
C9 N2 1.344(5) . ?
C9 O1 1.341(5) . ?
C10 C11 1.489(5) . ?
C10 C21 1.555(5) . ?
C10 N3 1.459(4) . ?
C11 C12 1.181(5) . ?
C12 C13 1.443(5) . ?
C13 C14 1.378(7) . ?
C13 C18 1.374(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.400(9) . ?
C15 H15 0.9300 . ?
C15 C16 1.344(11) . ?
C16 H16 0.9300 . ?
C16 C17 1.342(12) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(8) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.484(15) . ?
C19 N2 1.452(12) . ?
C19A H19C 0.9700 . ?
C19A H19D 0.9700 . ?
C19A C20A 1.54(3) . ?
C19A N2 1.38(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20A H20D 0.9600 . ?
C20A H20E 0.9600 . ?
C20A H20F 0.9600 . ?
C21 O2 1.195(5) . ?
C21 O3 1.309(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.480(14) . ?
C22 O3 1.506(10) . ?
C22A H22C 0.9700 . ?
C22A H22D 0.9700 . ?
C22A C23A 1.503(17) . ?
C22A O3 1.486(12) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24 N3 1.350(5) . ?
C24 O4 1.209(4) . ?
C24 O5 1.340(4) . ?
C25 C26 1.501(6) . ?
C25 C27 1.511(7) . ?
C25 C28 1.520(6) . ?
C25 O5 1.479(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N1 O1 1.429(4) . ?
N2 H2A 0.85(2) . ?
N3 H3A 0.86(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1 N3 0.93 2.87 3.596(5) 135.4 .
C4 H4 O1 0.93 2.83 3.488(5) 128.3 3
C5 H5 O1 0.93 2.94 3.541(5) 123.4 3
C20 H20C O2 0.96 2.57 3.267(8) 129.2 4_645
C22A H22C O1 0.97 2.81 3.506(12) 129.6 1_655
C23 H23B N1 0.96 2.51 3.343(12) 144.8 1_655
C28 H28A O1 0.96 2.74 3.525(7) 140.0 4_655
N2 H2A O4 0.85(2) 2.20(3) 2.882(4) 138(3) .
N3 H3A O2 0.86(2) 2.15(4) 2.601(4) 112(3) .
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
C1 C2 C3 C4 -0.2(8) . . . . ?
C1 C6 C7 C8 -44.2(6) . . . . ?
C1 C6 C7 N1 134.9(4) . . . . ?
C2 C1 C6 C5 -0.9(6) . . . . ?
C2 C1 C6 C7 -179.8(4) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C3 C4 C5 C6 -0.5(7) . . . . ?
C4 C5 C6 C1 0.8(6) . . . . ?
C4 C5 C6 C7 179.7(4) . . . . ?
C5 C6 C7 C8 136.9(4) . . . . ?
C5 C6 C7 N1 -44.0(5) . . . . ?
C6 C1 C2 C3 0.6(8) . . . . ?
C6 C7 C8 C9 178.1(4) . . . . ?
C6 C7 C8 C10 -8.6(6) . . . . ?
C6 C7 N1 O1 -178.6(3) . . . . ?
C7 C8 C9 N2 -179.5(4) . . . . ?
C7 C8 C9 O1 1.0(4) . . . . ?
C7 C8 C10 C11 -140.4(4) . . . . ?
C7 C8 C10 C21 -25.8(5) . . . . ?
C7 C8 C10 N3 93.2(4) . . . . ?
C7 N1 O1 C9 0.0(4) . . . . ?
C8 C7 N1 O1 0.7(4) . . . . ?
C8 C9 N2 C19 173.4(6) . . . . ?
C8 C9 N2 C19A -164(2) . . . . ?
C8 C9 O1 N1 -0.7(4) . . . . ?
C8 C10 C21 O2 133.2(4) . . . . ?
C8 C10 C21 O3 -49.5(4) . . . . ?
C8 C10 N3 C24 68.0(5) . . . . ?
C9 C8 C10 C11 31.5(5) . . . . ?
C9 C8 C10 C21 146.0(4) . . . . ?
C9 C8 C10 N3 -94.9(4) . . . . ?
C10 C8 C9 N2 7.0(7) . . . . ?
C10 C8 C9 O1 -172.5(3) . . . . ?
C10 C21 O3 C22 173.0(5) . . . . ?
C10 C21 O3 C22A -154.6(7) . . . . ?
C11 C10 C21 O2 -108.3(4) . . . . ?
C11 C10 C21 O3 69.0(4) . . . . ?
C11 C10 N3 C24 -57.5(5) . . . . ?
C12 C13 C14 C15 179.1(5) . . . . ?
C12 C13 C18 C17 -178.6(6) . . . . ?
C13 C14 C15 C16 0.2(11) . . . . ?
C14 C13 C18 C17 2.3(10) . . . . ?
C14 C15 C16 C17 1.0(14) . . . . ?
C15 C16 C17 C18 -0.5(15) . . . . ?
C16 C17 C18 C13 -1.2(13) . . . . ?
C18 C13 C14 C15 -1.9(8) . . . . ?
C20 C19 N2 C9 -178.0(7) . . . . ?
C20A C19A N2 C9 -110(4) . . . . ?
C21 C10 N3 C24 -168.8(3) . . . . ?
C23 C22 O3 C21 -169.8(7) . . . . ?
C23A C22A O3 C21 -95.6(12) . . . . ?
C26 C25 O5 C24 62.0(5) . . . . ?
C27 C25 O5 C24 -61.7(5) . . . . ?
C28 C25 O5 C24 179.8(4) . . . . ?
N1 C7 C8 C9 -1.1(4) . . . . ?
N1 C7 C8 C10 172.2(3) . . . . ?
N2 C9 O1 N1 179.8(4) . . . . ?
N3 C10 C21 O2 8.8(5) . . . . ?
N3 C10 C21 O3 -173.8(3) . . . . ?
N3 C24 O5 C25 174.4(3) . . . . ?
O1 C9 N2 C19 -7.1(8) . . . . ?
O1 C9 N2 C19A 16(2) . . . . ?
O2 C21 O3 C22 -9.8(7) . . . . ?
O2 C21 O3 C22A 22.5(9) . . . . ?
O4 C24 N3 C10 -4.6(6) . . . . ?
O4 C24 O5 C25 -5.5(6) . . . . ?
O5 C24 N3 C10 175.5(3) . . . . ?
