#------------------------------------------------------------------------------
#$Date: 2025-11-29 23:05:33 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303922 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/03/7160314.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_7160314
loop_
_publ_author_name
'Shang, Minghao'
'He, Junming'
'Gardiner, Michael G.'
'Nitsche, Christoph'
_publ_section_title
;
 Biocompatible synthesis of macrocyclic thiazole peptides from chiral
 α-amino nitriles.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9815
_journal_page_last               9818
_journal_paper_doi               10.1039/d4ob01989j
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C11 H20 N2 O2'
_chemical_formula_sum            'C11 H20 N2 O2'
_chemical_formula_weight         212.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-12-03 deposited with the CCDC.	2024-12-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.138(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.12630(10)
_cell_length_b                   10.4781(3)
_cell_length_c                   12.0133(3)
_cell_measurement_reflns_used    5065
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      77.7060
_cell_measurement_theta_min      5.6020
_cell_volume                     638.78(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -71.00   0.50    1.00    --  -46.45-129.00  51.00   82
  2  ω   -113.00 -62.00   0.50    1.00    --  -46.45-141.00-121.00  102
  3  ω    -87.00 -62.00   0.50    1.00    --  -46.45 141.00 -63.00   50
  4  ω    -76.00 -51.00   0.50    1.00    --  -46.45 129.00 124.00   50
  5  ω     45.00  91.00   0.50    1.00    --   46.45-129.00  51.00   92
  6  ω     43.00  99.00   0.50    1.00    --   46.45-141.00-121.00  112
  7  ω     85.00 115.00   0.50    2.00    --  107.75 141.00 -63.00   60
  8  ω     72.00 110.00   0.50    2.00    --  107.75-129.00  51.00   76
  9  ω    105.00 135.00   0.50    2.00    --  107.75 129.00 124.00   60
 10  ω     78.00 118.00   0.50    2.00    --  107.75-141.00-121.00   80
 11  ω     -5.00  28.00   0.50    1.00    --  -46.45  19.00 -90.00   66
 12  ω     -8.00  30.00   0.50    1.00    --  -46.45  19.00 120.00   76
 13  ω      1.00  27.00   0.50    1.00    --  -46.45  19.00 -30.00   52
 14  ω     -8.00  17.00   0.50    1.00    --  -46.45  19.00 150.00   50
 15  ω     -1.00  30.00   0.50    1.00    --  -46.45  19.00 -60.00   62
 16  ω    -18.00  14.00   0.50    1.00    --  -46.45  38.00  60.00   64
 17  ω     -2.00  23.00   0.50    1.00    --  -46.45  19.00-180.00   50
 18  ω     -5.00  21.00   0.50    1.00    --  -46.45  19.00  30.00   52
 19  ω     -8.00  17.00   0.50    1.00    --  -46.45  19.00-150.00   50
 20  ω     32.00  57.00   0.50    2.00    --  107.75 -30.00 -90.00   50
 21  ω     84.00 110.00   0.50    2.00    --  107.75-125.00   0.00   52
 22  ω     38.00  79.00   0.50    2.00    --  107.75-125.00   0.00   82
 23  ω     38.00  80.00   0.50    2.00    --  107.75-125.00 -30.00   84
 24  ω     32.00  58.00   0.50    2.00    --  107.75 -30.00 120.00   52
 25  ω     32.00  57.00   0.50    2.00    --  107.75 -30.00 150.00   50
 26  ω     32.00  57.00   0.50    2.00    --  107.75 -30.00-150.00   50
 27  ω     94.00 136.00   0.50    2.00    --  107.75  30.00-120.00   84
 28  ω    136.00 166.00   0.50    2.00    --  107.75  15.00 150.00   60
 29  ω     94.00 133.00   0.50    2.00    --  107.75  15.00 150.00   78
 30  ω     40.00  73.00   0.50    2.00    --  107.75 -45.00  90.00   66
 31  ω     32.00  57.00   0.50    2.00    --  107.75 -30.00  60.00   50
 32  ω    153.00 178.00   0.50    2.00    --  107.75 125.00 150.00   50
 33  ω    144.00 173.00   0.50    2.00    --  107.75  30.00-120.00   58
 34  ω     37.00  70.00   0.50    2.00    --  107.75 -95.00-150.00   66
 35  ω     76.00 103.00   0.50    2.00    --  107.75 -95.00-150.00   54
 36  ω     35.00  60.00   0.50    2.00    --  107.75 -45.00 -60.00   50
 37  ω    105.00 148.00   0.50    2.00    --  107.75 125.00 150.00   86
 38  ω     46.00  71.00   0.50    2.00    --  107.75 -45.00  30.00   50
 39  ω     87.00 112.00   0.50    2.00    --  107.75-125.00 -30.00   50
 40  ω     37.00  87.00   0.50    2.00    --  107.75 -95.00  60.00  100
 41  ω     55.00 104.00   0.50    2.00    --  107.75 -95.00-120.00   98
 42  ω     40.00 100.00   0.50    2.00    --  107.75 -95.00 150.00  120
 43  ω     41.00 110.00   0.50    2.00    --  107.75-125.00 150.00  138
 44  ω     42.00  86.00   0.50    2.00    --  107.75 -61.00-150.00   88
 45  ω     32.00  57.00   0.50    2.00    --  107.75 -30.00-120.00   50
 46  ω     41.00  89.00   0.50    2.00    --  107.75-125.00  30.00   96
 47  ω    103.00 129.00   0.50    2.00    --  107.75 125.00  60.00   52
 48  ω    150.00 175.00   0.50    2.00    --  107.75 125.00  60.00   50
 49  ω     95.00 101.00   0.50    2.00    --  107.75  45.00-150.00   12
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3032652000
_diffrn_orient_matrix_UB_12      0.0057016000
_diffrn_orient_matrix_UB_13      0.0223746000
_diffrn_orient_matrix_UB_21      -0.0119298000
_diffrn_orient_matrix_UB_22      0.1467252000
_diffrn_orient_matrix_UB_23      0.0046321000
_diffrn_orient_matrix_UB_31      -0.0091350000
_diffrn_orient_matrix_UB_32      -0.0063351000
_diffrn_orient_matrix_UB_33      0.1275329000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6805
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.907
_diffrn_reflns_theta_min         3.717
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
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    1.104
_exptl_crystal_description       prism
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1036 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2578
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0464
_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)+(0.0936P)²+0.0107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1284
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.897
_reflns_number_gt                2421
_reflns_number_total             2578
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01989j2.cif
_cod_data_source_block           ms-boc-ile-cnascaled010filtnon
_cod_depositor_comments          'Adding full bibliography for 7160314.cif.'
_cod_database_code               7160314
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H20N2O2
_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   0.884
_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.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C6(H6A,H6B,H6C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C),
 C11(H11A,H11B,H11C)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MiTeGen holder in oil'
_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 1.562
_oxdiff_exptl_absorpt_empirical_full_min 0.643
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
O1 O 0.7352(3) 0.46835(18) 0.66123(12) 0.0444(4) Uani 1 1 d . . . . .
O2 O 0.4038(3) 0.4990(2) 0.51703(12) 0.0489(5) Uani 1 1 d . . . . .
N1 N 0.3055(3) 0.4605(2) 0.68621(14) 0.0393(4) Uani 1 1 d . . . . .
H1 H 0.142(5) 0.465(3) 0.656(2) 0.032(6) Uiso 1 1 d . . . . .
N2 N 0.1799(6) 0.2147(2) 0.8536(2) 0.0592(6) Uani 1 1 d . . . . .
C1 C 0.2587(5) 0.3135(2) 0.83340(19) 0.0439(5) Uani 1 1 d . . . . .
C2 C 0.3558(4) 0.4415(2) 0.80669(17) 0.0376(5) Uani 1 1 d . . . . .
H2 H 0.550660 0.443860 0.830580 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2286(4) 0.5453(2) 0.87258(18) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.033700 0.542534 0.848886 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2827(6) 0.5189(3) 0.99866(19) 0.0510(6) Uani 1 1 d . . . . .
H4A H 0.470831 0.530787 1.025313 0.076 Uiso 1 1 calc R U . . .
H4B H 0.232293 0.430923 1.013306 0.076 Uiso 1 1 calc R U . . .
H4C H 0.179809 0.578014 1.038333 0.076 Uiso 1 1 calc R U . . .
C5 C 0.3268(6) 0.6775(3) 0.8447(2) 0.0503(6) Uani 1 1 d . . . . .
H5A H 0.513578 0.686354 0.878460 0.060 Uiso 1 1 calc R U . . .
H5B H 0.318251 0.685272 0.762173 0.060 Uiso 1 1 calc R U . . .
C6 C 0.1692(7) 0.7847(3) 0.8869(3) 0.0603(7) Uani 1 1 d . . . . .
H6A H -0.016997 0.775201 0.855645 0.091 Uiso 1 1 calc R U . . .
H6B H 0.234740 0.866787 0.863313 0.091 Uiso 1 1 calc R U . . .
H6C H 0.187634 0.781572 0.969213 0.091 Uiso 1 1 calc R U . . .
C7 C 0.5030(4) 0.4755(2) 0.62409(16) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.5793(4) 0.5201(3) 0.43038(18) 0.0491(6) Uani 1 1 d . . . . .
C9 C 0.7508(6) 0.6370(3) 0.4599(2) 0.0534(6) Uani 1 1 d . . . . .
H9A H 0.640432 0.708403 0.477859 0.080 Uiso 1 1 calc R U . . .
H9B H 0.840038 0.660020 0.395813 0.080 Uiso 1 1 calc R U . . .
H9C H 0.882567 0.618023 0.525194 0.080 Uiso 1 1 calc R U . . .
C10 C 0.3838(6) 0.5440(7) 0.3251(3) 0.112(2) Uani 1 1 d . . . . .
H10A H 0.272141 0.468578 0.308579 0.168 Uiso 1 1 calc R U . . .
H10B H 0.479698 0.561235 0.261725 0.168 Uiso 1 1 calc R U . . .
H10C H 0.273588 0.617756 0.337225 0.168 Uiso 1 1 calc R U . . .
C11 C 0.7397(6) 0.4006(3) 0.4183(2) 0.0601(8) Uani 1 1 d . . . . .
H11A H 0.874173 0.391327 0.484369 0.090 Uiso 1 1 calc R U . . .
H11B H 0.825273 0.407310 0.350553 0.090 Uiso 1 1 calc R U . . .
H11C H 0.623259 0.326002 0.412070 0.090 Uiso 1 1 calc R U . . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0352
1 0 0 0.0352
0 -1 0 0.0837
0 1 0 0.0837
0 0 1 0.0975
0 0 -1 0.0975
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
C7 O2 C8 121.04(16) . . ?
C2 N1 H1 117.0(16) . . ?
C7 N1 H1 121.1(16) . . ?
C7 N1 C2 121.85(17) . . ?
N2 C1 C2 179.1(3) . . ?
N1 C2 C1 108.85(19) . . ?
N1 C2 H2 108.2 . . ?
N1 C2 C3 112.82(18) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C3 110.36(17) . . ?
C3 C2 H2 108.2 . . ?
C2 C3 H3 108.1 . . ?
C4 C3 C2 110.53(19) . . ?
C4 C3 H3 108.1 . . ?
C4 C3 C5 111.3(2) . . ?
C5 C3 C2 110.55(18) . . ?
C5 C3 H3 108.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.0 . . ?
C3 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 C3 113.1(2) . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O1 C7 O2 125.80(18) . . ?
O1 C7 N1 124.30(19) . . ?
O2 C7 N1 109.90(17) . . ?
O2 C8 C9 110.1(2) . . ?
O2 C8 C10 102.38(19) . . ?
O2 C8 C11 109.6(2) . . ?
C10 C8 C9 110.7(3) . . ?
C11 C8 C9 112.6(2) . . ?
C11 C8 C10 111.1(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C7 1.213(3) . ?
O2 C7 1.337(2) . ?
O2 C8 1.486(2) . ?
N1 H1 0.87(3) . ?
N1 C2 1.447(3) . ?
N1 C7 1.349(3) . ?
N2 C1 1.150(4) . ?
C1 C2 1.481(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.543(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.526(3) . ?
C3 C5 1.527(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.512(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 C9 1.521(4) . ?
C8 C10 1.519(4) . ?
C8 C11 1.516(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
_geom_hbond_publ_flag
N1 H1 O1 0.87(3) 2.10(3) 2.897(2) 153(2) 1_455 yes
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
N1 C2 C3 C4 178.73(19) . . . . ?
N1 C2 C3 C5 -57.6(2) . . . . ?
C1 C2 C3 C4 56.7(2) . . . . ?
C1 C2 C3 C5 -179.6(2) . . . . ?
C2 N1 C7 O1 3.8(4) . . . . ?
C2 N1 C7 O2 -176.2(2) . . . . ?
C2 C3 C5 C6 168.0(2) . . . . ?
C4 C3 C5 C6 -68.8(3) . . . . ?
C7 O2 C8 C9 -61.6(3) . . . . ?
C7 O2 C8 C10 -179.3(4) . . . . ?
C7 O2 C8 C11 62.7(3) . . . . ?
C7 N1 C2 C1 -116.3(2) . . . . ?
C7 N1 C2 C3 120.8(2) . . . . ?
C8 O2 C7 O1 -0.4(4) . . . . ?
C8 O2 C7 N1 179.7(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9996 -0.0003 0.0001 -0.3032 0.0119 0.0091
0.9996 0.0003 -0.0001 0.3032 -0.0119 -0.0091
-0.0002 -1.0002 -0.0004 -0.0058 -0.1467 0.0063
0.0002 1.0002 0.0004 0.0058 0.1467 -0.0063
-0.0001 -0.0003 1.0002 0.0223 0.0046 0.1276
0.0001 0.0003 -1.0002 -0.0223 -0.0046 -0.1276
