#------------------------------------------------------------------------------
#$Date: 2023-06-29 10:59:56 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284543 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/17/7131746.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_7131746
loop_
_publ_author_name
'Chen, Yun-Xuan'
'Han, Tian-Jiao'
'Xiao, Xiao'
'Wang, Min-Can'
'Mei, Guang-Jian'
_publ_section_title
;
 Catalytic asymmetric interrupted Attanasi reaction: access to fused
 2,3-dihydropyrroles with vicinal quaternary carbons.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8103
_journal_page_last               8106
_journal_paper_doi               10.1039/d3cc02172f
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C32 H48 N4 O14'
_chemical_formula_sum            'C32 H48 N4 O14'
_chemical_formula_weight         712.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-01 deposited with the CCDC.	2023-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                102.528(7)
_cell_angle_beta                 110.036(8)
_cell_angle_gamma                102.007(8)
_cell_formula_units_Z            1
_cell_length_a                   9.4928(9)
_cell_length_b                   9.8026(9)
_cell_length_c                   11.3802(8)
_cell_measurement_reflns_used    2550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1960
_cell_measurement_theta_min      4.3290
_cell_volume                     924.02(16)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  90.00   73
  2  ω   -108.00 -35.00   1.00    1.00    --  -33.50 178.00  30.00   73
  3  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00 -30.00   93
  4  ω   -104.00 -11.00   1.00    1.00    --  -33.50 -37.00-120.00   93
  5  ω    -52.00  35.00   1.00    1.00    --  -33.50  57.00 120.00   87
  6  ω    -62.00  36.00   1.00    1.00    --  -33.50  77.00-150.00   98
  7  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00-150.00   75
  8  ω     61.00 110.00   1.00    1.00    --   36.47 178.00  60.00   49
  9  ω      1.00  76.00   1.00    1.00    --   36.47 -99.00  60.00   75
 10  ω     40.00 109.00   1.00    1.00    --  108.00-111.00 -90.00   69
 11  ω     66.00 104.00   1.00    1.00    --  108.00 178.00  30.00   38
 12  ω     88.00 178.00   1.00    1.00    --  108.00  45.00 150.00   90
 13  ω     49.00 128.00   1.00    1.00    --  108.00 -45.00  60.00   79
 14  ω     88.00 176.00   1.00    1.00    --  108.00  45.00  90.00   88
 15  ω     42.00 103.00   1.00    1.00    --  108.00 -94.00  30.00   61
 16  ω     95.00 136.00   1.00    1.00    --  108.00 -77.00  90.00   41
 17  ω    128.00 169.00   1.00    1.00    --  108.00  45.00   0.00   41
 18  ω     39.00  99.00   1.00    1.00    --  108.00 -94.00  90.00   60
 19  ω    110.00 176.00   1.00    1.00    --  108.00 111.00  30.00   66
 20  ω    133.00 175.00   1.00    1.00    --  108.00  74.00 123.00   42
 21  ω    126.00 177.00   1.00    1.00    --  108.00  77.00-180.00   51
 22  ω     80.00 106.00   1.00    1.00    --  108.00 -94.00 120.00   26
 23  ω     38.00 100.00   1.00    1.00    --  108.00 -94.00 -30.00   62
 24  ω    153.00 178.00   1.00    1.00    --  108.00  45.00-120.00   25
 25  ω     88.00 133.00   1.00    1.00    --  108.00  45.00-120.00   45
;
_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      -0.0054249000
_diffrn_orient_matrix_UB_12      0.1529011000
_diffrn_orient_matrix_UB_13      0.0649778000
_diffrn_orient_matrix_UB_21      0.1679945000
_diffrn_orient_matrix_UB_22      0.0353919000
_diffrn_orient_matrix_UB_23      0.1048260000
_diffrn_orient_matrix_UB_31      0.0686483000
_diffrn_orient_matrix_UB_32      0.0632519000
_diffrn_orient_matrix_UB_33      -0.0884148000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6573
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.583
_diffrn_reflns_theta_min         4.355
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
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    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0076(11)
_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   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3435
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0544
_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)+(0.0664P)²+0.2851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1674
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2472
_reflns_number_total             3435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc02172f2.cif
_cod_data_source_block           20230339
_cod_original_cell_volume        924.02(15)
_cod_database_code               7131746
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H20N3O4
_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   0.920
_shelx_estimated_absorpt_t_min   0.883
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9-C10
 1.56 with sigma of 0.02
 C10A-C9A
 1.56 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
4. Others
 Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(C10A)=Sof(H10D)=Sof(H10E)=Sof(H10F)=1-FVAR(1)
 Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(C10)=Sof(H10A)=Sof(H10B)=Sof(H10C)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C9A(H9AA,H9AB), C11(H11A,H11B)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C10A(H10D,H10E,H10F),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
5.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 1.848
_oxdiff_exptl_absorpt_empirical_full_min 0.890
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.8542(3) 0.8786(3) 0.8989(2) 0.0452(6) Uani 1 1 d . . . . .
C2 C 0.9268(3) 1.0036(3) 0.8538(2) 0.0443(6) Uani 1 1 d . . . . .
C3 C 0.7828(3) 1.0443(3) 0.7799(2) 0.0467(6) Uani 1 1 d . . . . .
C4 C 0.6687(3) 0.9982(3) 0.8204(2) 0.0488(6) Uani 1 1 d . . . . .
C5 C 0.5142(3) 1.0282(4) 0.7937(3) 0.0645(8) Uani 1 1 d . . . . .
H5A H 0.4453 0.9550 0.8101 0.097 Uiso 1 1 calc GR . . . .
H5B H 0.4670 1.0251 0.7035 0.097 Uiso 1 1 calc GR . . . .
H5C H 0.5312 1.1235 0.8505 0.097 Uiso 1 1 calc GR . . . .
C6 C 1.0110(3) 0.9536(3) 0.7673(2) 0.0486(6) Uani 1 1 d . . . . .
C7 C 0.9757(4) 0.8235(4) 0.5543(3) 0.0823(10) Uani 1 1 d . . . . .
H7A H 0.8958 0.7892 0.4661 0.123 Uiso 1 1 calc GR . . . .
H7B H 1.0145 0.7446 0.5739 0.123 Uiso 1 1 calc GR . . . .
H7C H 1.0608 0.9025 0.5620 0.123 Uiso 1 1 calc GR . . . .
C8 C 0.7933(3) 1.1415(3) 0.7016(3) 0.0544(6) Uani 1 1 d . . . . .
C9 C 0.6717(10) 1.2823(9) 0.5786(9) 0.078(2) Uani 0.632(6) 1 d D U P A 1
H9A H 0.6868 1.2459 0.4989 0.093 Uiso 0.632(6) 1 calc R . P A 1
H9B H 0.7598 1.3689 0.6370 0.093 Uiso 0.632(6) 1 calc R . P A 1
C9A C 0.632(2) 1.2349(16) 0.5410(18) 0.078(2) Uani 0.368(6) 1 d D U P A 2
H9AA H 0.5273 1.1891 0.4717 0.093 Uiso 0.368(6) 1 calc R . P A 2
H9AB H 0.7095 1.2309 0.5032 0.093 Uiso 0.368(6) 1 calc R . P A 2
C10 C 0.5194(8) 1.3169(8) 0.5472(7) 0.0981(19) Uani 0.632(6) 1 d D . P A 1
H10A H 0.5151 1.3822 0.4952 0.147 Uiso 0.632(6) 1 calc GR . P A 1
H10B H 0.5122 1.3629 0.6276 0.147 Uiso 0.632(6) 1 calc GR . P A 1
H10C H 0.4332 1.2278 0.4988 0.147 Uiso 0.632(6) 1 calc GR . P A 1
C10A C 0.6543(15) 1.3906(14) 0.6156(12) 0.0981(19) Uani 0.368(6) 1 d D . P A 2
H10D H 0.6563 1.4513 0.5600 0.147 Uiso 0.368(6) 1 calc GR . P A 2
H10E H 0.7520 1.4271 0.6924 0.147 Uiso 0.368(6) 1 calc GR . P A 2
H10F H 0.5687 1.3925 0.6419 0.147 Uiso 0.368(6) 1 calc GR . P A 2
C11 C 1.0377(3) 1.1392(3) 0.9749(2) 0.0464(6) Uani 1 1 d . . . . .
H11A H 1.1041 1.2008 0.9460 0.056 Uiso 1 1 calc R . . . .
H11B H 0.9720 1.1941 0.9983 0.056 Uiso 1 1 calc R . . . .
C12 C 0.4935(3) 0.7205(3) 0.8597(3) 0.0539(6) Uani 1 1 d . . . . .
C13 C 0.2655(3) 0.5451(3) 0.8583(3) 0.0603(7) Uani 1 1 d . . . . .
C14 C 0.3035(4) 0.4079(3) 0.8088(3) 0.0722(9) Uani 1 1 d . . . . .
H14A H 0.3362 0.4151 0.7388 0.108 Uiso 1 1 calc GR . . . .
H14B H 0.2115 0.3243 0.7767 0.108 Uiso 1 1 calc GR . . . .
H14C H 0.3869 0.3969 0.8794 0.108 Uiso 1 1 calc GR . . . .
C15 C 0.2136(4) 0.5377(4) 0.9692(4) 0.0854(11) Uani 1 1 d . . . . .
H15A H 0.2902 0.5140 1.0355 0.128 Uiso 1 1 calc GR . . . .
H15B H 0.1135 0.4633 0.9353 0.128 Uiso 1 1 calc GR . . . .
H15C H 0.2040 0.6310 1.0072 0.128 Uiso 1 1 calc GR . . . .
C16 C 0.1463(4) 0.5777(4) 0.7501(4) 0.0996(13) Uani 1 1 d . . . . .
H16A H 0.1320 0.6696 0.7852 0.149 Uiso 1 1 calc GR . . . .
H16B H 0.0477 0.5008 0.7140 0.149 Uiso 1 1 calc GR . . . .
H16C H 0.1832 0.5835 0.6821 0.149 Uiso 1 1 calc GR . . . .
N1 N 0.7183(2) 0.9216(2) 0.9074(2) 0.0482(5) Uani 1 1 d . . . . .
N2 N 0.6173(3) 0.8402(3) 0.9465(2) 0.0545(6) Uani 1 1 d . . . . .
H2 H 0.638(3) 0.862(3) 1.029(3) 0.060(8) Uiso 1 1 d . . . . .
O1 O 0.8035(2) 0.73633(19) 0.80638(17) 0.0582(5) Uani 1 1 d . . . . .
H1 H 0.7231 0.7269 0.7434 0.087 Uiso 1 1 calc GR . . . .
O2 O 1.1500(2) 0.9806(3) 0.80299(19) 0.0705(6) Uani 1 1 d . . . . .
O3 O 0.9095(2) 0.8750(2) 0.64568(17) 0.0633(5) Uani 1 1 d . . . . .
O4 O 0.9124(2) 1.1940(2) 0.6891(2) 0.0710(6) Uani 1 1 d . . . . .
O5 O 0.6574(2) 1.1675(3) 0.6439(2) 0.0812(7) Uani 1 1 d . . . . .
O6 O 0.4639(2) 0.6732(2) 0.74425(19) 0.0708(6) Uani 1 1 d . . . . .
O7 O 0.4123(2) 0.6712(2) 0.92575(18) 0.0609(5) 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
C11 C1 C2 116.2(2) 2_777 . ?
N1 C1 C2 99.69(19) . . ?
N1 C1 C11 114.45(19) . 2_777 ?
O1 C1 C2 113.76(19) . . ?
O1 C1 C11 102.8(2) . 2_777 ?
O1 C1 N1 110.33(19) . . ?
C3 C2 C1 102.11(19) . . ?
C3 C2 C6 112.77(19) . . ?
C3 C2 C11 107.4(2) . . ?
C6 C2 C1 112.3(2) . . ?
C6 C2 C11 111.59(19) . . ?
C11 C2 C1 110.15(19) . . ?
C4 C3 C2 108.6(2) . . ?
C4 C3 C8 129.9(2) . . ?
C8 C3 C2 120.4(2) . . ?
C3 C4 C5 130.2(2) . . ?
C3 C4 N1 109.6(2) . . ?
N1 C4 C5 120.0(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O2 C6 C2 125.2(2) . . ?
O2 C6 O3 123.3(2) . . ?
O3 C6 C2 111.5(2) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
O4 C8 C3 123.7(3) . . ?
O4 C8 O5 123.1(2) . . ?
O5 C8 C3 113.2(2) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.8 . . ?
C10 C9 H9B 110.8 . . ?
O5 C9 H9A 110.8 . . ?
O5 C9 H9B 110.8 . . ?
O5 C9 C10 104.9(7) . . ?
H9AA C9A H9AB 109.3 . . ?
C10A C9A H9AA 111.5 . . ?
C10A C9A H9AB 111.5 . . ?
O5 C9A H9AA 111.5 . . ?
O5 C9A H9AB 111.5 . . ?
O5 C9A C10A 101.4(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9A C10A H10D 109.5 . . ?
C9A C10A H10E 109.5 . . ?
C9A C10A H10F 109.5 . . ?
H10D C10A H10E 109.5 . . ?
H10D C10A H10F 109.5 . . ?
H10E C10A H10F 109.5 . . ?
C1 C11 C2 121.1(2) 2_777 . ?
C1 C11 H11A 107.1 2_777 . ?
C1 C11 H11B 107.1 2_777 . ?
C2 C11 H11A 107.1 . . ?
C2 C11 H11B 107.1 . . ?
H11A C11 H11B 106.8 . . ?
O6 C12 N2 124.6(2) . . ?
O6 C12 O7 127.7(2) . . ?
O7 C12 N2 107.7(2) . . ?
C14 C13 C15 110.9(3) . . ?
C16 C13 C14 112.6(3) . . ?
C16 C13 C15 111.3(3) . . ?
O7 C13 C14 109.5(2) . . ?
O7 C13 C15 101.8(2) . . ?
O7 C13 C16 110.1(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 N1 C1 110.93(19) . . ?
N2 N1 C1 120.4(2) . . ?
N2 N1 C4 122.3(2) . . ?
C12 N2 N1 122.0(2) . . ?
C12 N2 H2 120.1(19) . . ?
N1 N2 H2 117.8(19) . . ?
C1 O1 H1 109.5 . . ?
C6 O3 C7 116.5(2) . . ?
C8 O5 C9 113.7(4) . . ?
C8 O5 C9A 122.0(8) . . ?
C12 O7 C13 121.4(2) . . ?
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 C2 1.551(3) . ?
C1 C11 1.522(3) 2_777 ?
C1 N1 1.464(3) . ?
C1 O1 1.422(3) . ?
C2 C3 1.522(3) . ?
C2 C6 1.530(3) . ?
C2 C11 1.550(3) . ?
C3 C4 1.348(3) . ?
C3 C8 1.450(3) . ?
C4 C5 1.498(4) . ?
C4 N1 1.384(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 O2 1.190(3) . ?
C6 O3 1.324(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 O3 1.443(3) . ?
C8 O4 1.210(3) . ?
C8 O5 1.337(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.495(10) . ?
C9 O5 1.486(10) . ?
C9A H9AA 0.9700 . ?
C9A H9AB 0.9700 . ?
C9A C10A 1.509(15) . ?
C9A O5 1.44(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C10A H10D 0.9600 . ?
C10A H10E 0.9600 . ?
C10A H10F 0.9600 . ?
C11 C1 1.522(3) 2_777 ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.364(3) . ?
C12 O6 1.204(3) . ?
C12 O7 1.338(3) . ?
C13 C14 1.506(4) . ?
C13 C15 1.515(4) . ?
C13 C16 1.505(4) . ?
C13 O7 1.482(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.372(3) . ?
N2 H2 0.85(3) . ?
O1 H1 0.8200 . ?
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
N2 H2 O2 0.85(3) 2.21(3) 2.826(3) 129(2) 2_777
O1 H1 O6 0.82 2.41 2.949(3) 124.0 .
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 21.0(3) . . . . ?
C1 C2 C3 C8 -169.6(2) . . . . ?
C1 C2 C6 O2 -102.6(3) . . . . ?
C1 C2 C6 O3 77.4(3) . . . . ?
C1 C2 C11 C1 39.7(3) . . . 2_777 ?
C1 N1 N2 C12 -86.0(3) . . . . ?
C2 C1 N1 C4 28.1(2) . . . . ?
C2 C1 N1 N2 -179.3(2) . . . . ?
C2 C3 C4 C5 170.5(3) . . . . ?
C2 C3 C4 N1 -4.1(3) . . . . ?
C2 C3 C8 O4 0.7(4) . . . . ?
C2 C3 C8 O5 -179.5(2) . . . . ?
C2 C6 O3 C7 179.1(2) . . . . ?
C3 C2 C6 O2 142.7(3) . . . . ?
C3 C2 C6 O3 -37.4(3) . . . . ?
C3 C2 C11 C1 150.2(2) . . . 2_777 ?
C3 C4 N1 C1 -16.3(3) . . . . ?
C3 C4 N1 N2 -168.3(2) . . . . ?
C3 C8 O5 C9 172.1(4) . . . . ?
C3 C8 O5 C9A -166.8(7) . . . . ?
C4 C3 C8 O4 167.5(3) . . . . ?
C4 C3 C8 O5 -12.6(4) . . . . ?
C4 N1 N2 C12 63.5(4) . . . . ?
C5 C4 N1 C1 168.5(2) . . . . ?
C5 C4 N1 N2 16.4(4) . . . . ?
C6 C2 C3 C4 141.8(2) . . . . ?
C6 C2 C3 C8 -48.8(3) . . . . ?
C6 C2 C11 C1 -85.8(3) . . . 2_777 ?
C8 C3 C4 C5 2.4(5) . . . . ?
C8 C3 C4 N1 -172.2(3) . . . . ?
C10 C9 O5 C8 -168.1(5) . . . . ?
C10A C9A O5 C8 -101.8(12) . . . . ?
C11 C1 C2 C3 -151.4(2) 2_777 . . . ?
C11 C1 C2 C6 87.5(3) 2_777 . . . ?
C11 C1 C2 C11 -37.6(3) 2_777 . . . ?
C11 C1 N1 C4 152.7(2) 2_777 . . . ?
C11 C1 N1 N2 -54.6(3) 2_777 . . . ?
C11 C2 C3 C4 -94.9(2) . . . . ?
C11 C2 C3 C8 74.5(3) . . . . ?
C11 C2 C6 O2 21.7(4) . . . . ?
C11 C2 C6 O3 -158.4(2) . . . . ?
C14 C13 O7 C12 65.9(3) . . . . ?
C15 C13 O7 C12 -176.6(3) . . . . ?
C16 C13 O7 C12 -58.4(4) . . . . ?
N1 C1 C2 C3 -28.0(2) . . . . ?
N1 C1 C2 C6 -149.03(19) . . . . ?
N1 C1 C2 C11 85.9(2) . . . . ?
N2 C12 O7 C13 177.3(2) . . . . ?
O1 C1 C2 C3 89.4(2) . . . . ?
O1 C1 C2 C6 -31.6(3) . . . . ?
O1 C1 C2 C11 -156.7(2) . . . . ?
O1 C1 N1 C4 -91.9(2) . . . . ?
O1 C1 N1 N2 60.8(3) . . . . ?
O2 C6 O3 C7 -1.0(4) . . . . ?
O4 C8 O5 C9 -8.0(6) . . . . ?
O4 C8 O5 C9A 13.1(8) . . . . ?
O6 C12 N2 N1 2.1(5) . . . . ?
O6 C12 O7 C13 -0.9(5) . . . . ?
O7 C12 N2 N1 -176.1(2) . . . . ?
