#------------------------------------------------------------------------------
#$Date: 2023-10-11 00:57:05 +0300 (Wed, 11 Oct 2023) $
#$Revision: 286878 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132199.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_7132199
loop_
_publ_author_name
'Woelk, Kyla'
'Dhake, Kushal'
'Schley, Nathan D.'
'Leitch, David'
_publ_section_title
;
 Enolate addition to bicyclobutanes enables expedient access to
 2-oxo-bicyclohexane scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC04234K
_journal_year                    2023
_chemical_formula_moiety         'C18 H24 N2 O3'
_chemical_formula_sum            'C18 H24 N2 O3'
_chemical_formula_weight         316.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-09-29 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9398(2)
_cell_length_b                   12.0803(2)
_cell_length_c                   16.6377(3)
_cell_measurement_reflns_used    11115
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.6720
_cell_measurement_theta_min      5.2750
_cell_volume                     3203.72(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.71a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.71a (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      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_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 -39.00   1.00    1.00    --  -35.84-178.00  30.00   69
  2  ω   -107.00  -6.00   1.00    1.00    --  -35.84 -19.00 -60.00  101
  3  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00 150.00   88
  4  ω   -108.00 -39.00   1.00    1.00    --  -35.84-178.00 120.00   69
  5  ω     61.00 108.00   1.00    1.00    --   35.84 178.00 150.00   47
  6  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  60.00   84
  7  ω      6.00  74.00   1.00    1.00    --   35.84 -99.00 -30.00   68
  8  ω     58.00 108.00   1.00    1.00    --   35.84-178.00-150.00   50
  9  ω     40.00 126.00   1.00    2.00    --  108.40 -45.00  60.00   86
 10  ω    103.00 176.00   1.00    2.00    --  108.40  77.00  90.00   73
 11  ω    103.00 176.00   1.00    2.00    --  108.40  77.00  30.00   73
 12  ω     40.00 124.00   1.00    2.00    --  108.40-140.00 -70.00   84
 13  ω    104.00 175.00   1.00    2.00    --  108.40 111.00  60.00   71
 14  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00   0.00   68
 15  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00 150.00   68
 16  ω     42.00 126.00   1.00    2.00    --  108.40 -61.00   0.00   84
 17  ω     39.00 107.00   1.00    2.00    --  108.40 -94.00 -90.00   68
 18  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00-120.00   88
 19  ω    -55.00  -1.00   1.00    1.00    --  -35.84  38.00 -30.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0276042000
_diffrn_orient_matrix_UB_12      -0.0743363000
_diffrn_orient_matrix_UB_13      0.0703169000
_diffrn_orient_matrix_UB_21      0.0370496000
_diffrn_orient_matrix_UB_22      -0.0839609000
_diffrn_orient_matrix_UB_23      -0.0601170000
_diffrn_orient_matrix_UB_31      0.0849046000
_diffrn_orient_matrix_UB_32      0.0607507000
_diffrn_orient_matrix_UB_33      0.0033883000
_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  0.0478
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18157
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.618
_diffrn_reflns_theta_min         5.308
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.722
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.598
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.71a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0388
_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)+(0.0405P)²+1.3355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0952
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2857
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04234k2.cif
_cod_data_source_block           kjw-2023-423
_cod_database_code               7132199
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H25N2O3
_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   0.938
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_olex2_date_sample_data_collection 2023-09-27
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.154
_oxdiff_exptl_absorpt_empirical_full_min 0.900
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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 0.69090(6) 0.86168(8) 0.56815(6) 0.0230(2) Uani 1 1 d . . . . .
O2 O 0.60042(6) 0.56184(7) 0.49362(5) 0.0182(2) Uani 1 1 d . . . . .
H2 H 0.5497(14) 0.5608(17) 0.4589(14) 0.059(6) Uiso 1 1 d . . . . .
O3 O 0.82692(6) 0.69362(8) 0.34537(6) 0.0266(2) Uani 1 1 d . . . . .
N1 N 0.76756(7) 0.73262(9) 0.50334(7) 0.0186(2) Uani 1 1 d . . . . .
N2 N 0.53357(7) 0.44241(9) 0.61243(6) 0.0180(2) Uani 1 1 d . . . . .
H2A H 0.5832(11) 0.4205(14) 0.5884(10) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.70706(8) 0.76305(10) 0.55596(7) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.65792(8) 0.67700(10) 0.60193(7) 0.0163(3) Uani 1 1 d . . . . .
C3 C 0.57936(8) 0.62772(10) 0.56092(8) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.5389(9) 0.6842(12) 0.5440(9) 0.014(3) Uiso 1 1 d . . . . .
C4 C 0.54360(8) 0.55919(10) 0.63421(8) 0.0173(3) Uani 1 1 d . . . . .
H4 H 0.4867(10) 0.5865(12) 0.6524(9) 0.018(4) Uiso 1 1 d . . . . .
C5 C 0.61042(8) 0.58880(11) 0.69735(8) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.6043(10) 0.5588(13) 0.7504(11) 0.026(4) Uiso 1 1 d . . . . .
C6 C 0.69365(8) 0.57637(11) 0.65013(8) 0.0180(3) Uani 1 1 d . . . . .
H6A H 0.7405(10) 0.5978(13) 0.6822(9) 0.018(4) Uiso 1 1 d . . . . .
H6B H 0.7044(9) 0.5085(13) 0.6226(10) 0.020(4) Uiso 1 1 d . . . . .
C7 C 0.61829(8) 0.71485(11) 0.68255(8) 0.0200(3) Uani 1 1 d . . . . .
H7A H 0.5641(10) 0.7599(14) 0.6791(10) 0.027(4) Uiso 1 1 d . . . . .
H7B H 0.6619(10) 0.7512(13) 0.7180(10) 0.023(4) Uiso 1 1 d . . . . .
C8 C 0.81543(9) 0.81675(11) 0.46006(9) 0.0231(3) Uani 1 1 d . . . . .
H8A H 0.875770 0.809688 0.473197 0.028 Uiso 1 1 calc R U . . .
H8B H 0.796526 0.891443 0.476535 0.028 Uiso 1 1 calc R U . . .
C9 C 0.80254(9) 0.80193(11) 0.37051(9) 0.0251(3) Uani 1 1 d . . . . .
H9A H 0.742693 0.814046 0.357242 0.030 Uiso 1 1 calc R U . . .
H9B H 0.836078 0.857753 0.341091 0.030 Uiso 1 1 calc R U . . .
C10 C 0.77954(9) 0.61118(11) 0.38730(8) 0.0227(3) Uani 1 1 d . . . . .
H10A H 0.798051 0.536825 0.369660 0.027 Uiso 1 1 calc R U . . .
H10B H 0.719436 0.619153 0.373458 0.027 Uiso 1 1 calc R U . . .
C11 C 0.79003(8) 0.62069(10) 0.47808(8) 0.0198(3) Uani 1 1 d . . . . .
H11A H 0.753441 0.566162 0.505360 0.024 Uiso 1 1 calc R U . . .
H11B H 0.848909 0.604778 0.493097 0.024 Uiso 1 1 calc R U . . .
C12 C 0.51581(9) 0.36987(11) 0.68165(8) 0.0217(3) Uani 1 1 d . . . . .
H12A H 0.461108 0.390349 0.705592 0.026 Uiso 1 1 calc R U . . .
H12B H 0.559685 0.380043 0.723112 0.026 Uiso 1 1 calc R U . . .
C13 C 0.51367(8) 0.25029(11) 0.65563(7) 0.0184(3) Uani 1 1 d . . . . .
C14 C 0.44854(8) 0.20985(11) 0.60781(8) 0.0190(3) Uani 1 1 d . . . . .
H14 H 0.404368 0.257982 0.592055 0.023 Uiso 1 1 calc R U . . .
C15 C 0.44755(8) 0.10030(11) 0.58304(8) 0.0212(3) Uani 1 1 d . . . . .
H15 H 0.403363 0.074226 0.549729 0.025 Uiso 1 1 calc R U . . .
C16 C 0.51093(9) 0.02858(11) 0.60674(8) 0.0224(3) Uani 1 1 d . . . . .
H16 H 0.509689 -0.046844 0.590632 0.027 Uiso 1 1 calc R U . . .
C17 C 0.57592(9) 0.06769(12) 0.65401(8) 0.0241(3) Uani 1 1 d . . . . .
H17 H 0.619500 0.018959 0.670305 0.029 Uiso 1 1 calc R U . . .
C18 C 0.57770(8) 0.17787(12) 0.67770(8) 0.0222(3) Uani 1 1 d . . . . .
H18 H 0.623119 0.204206 0.709339 0.027 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
3 -7 -3 0.0638
-2 7 3 0.1015
-8 -4 5 0.1048
4 4 -8 0.0746
6 -1 9 0.0343
-4 3 -9 0.0319
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
C3 O2 H2 106.0(13) . . ?
C9 O3 C10 110.57(10) . . ?
C1 N1 C8 120.14(11) . . ?
C1 N1 C11 127.76(11) . . ?
C11 N1 C8 111.97(10) . . ?
C4 N2 H2A 106.8(11) . . ?
C4 N2 C12 113.57(10) . . ?
C12 N2 H2A 109.4(11) . . ?
O1 C1 N1 121.11(12) . . ?
O1 C1 C2 118.20(11) . . ?
N1 C1 C2 120.69(11) . . ?
C1 C2 C3 117.51(10) . . ?
C1 C2 C6 127.31(11) . . ?
C1 C2 C7 116.50(10) . . ?
C3 C2 C6 102.83(10) . . ?
C3 C2 C7 99.52(10) . . ?
C7 C2 C6 86.22(9) . . ?
O2 C3 C2 111.97(10) . . ?
O2 C3 H3 108.7(9) . . ?
O2 C3 C4 113.69(10) . . ?
C2 C3 H3 113.1(8) . . ?
C2 C3 C4 98.82(10) . . ?
C4 C3 H3 110.4(9) . . ?
N2 C4 C3 110.66(10) . . ?
N2 C4 H4 106.9(9) . . ?
N2 C4 C5 117.93(11) . . ?
C3 C4 H4 112.6(8) . . ?
C5 C4 C3 98.94(10) . . ?
C5 C4 H4 109.9(8) . . ?
C4 C5 H5 118.0(10) . . ?
C4 C5 C6 102.95(10) . . ?
C4 C5 C7 100.15(10) . . ?
C6 C5 H5 121.2(10) . . ?
C7 C5 H5 121.8(9) . . ?
C7 C5 C6 86.86(10) . . ?
C2 C6 H6A 111.2(9) . . ?
C2 C6 H6B 119.1(9) . . ?
C5 C6 C2 82.69(9) . . ?
C5 C6 H6A 111.1(9) . . ?
C5 C6 H6B 118.7(9) . . ?
H6A C6 H6B 111.2(13) . . ?
C2 C7 H7A 116.9(9) . . ?
C2 C7 H7B 110.6(9) . . ?
C5 C7 C2 83.14(9) . . ?
C5 C7 H7A 117.7(9) . . ?
C5 C7 H7B 113.0(9) . . ?
H7A C7 H7B 112.5(13) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.38(11) . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
O3 C9 C8 111.07(11) . . ?
O3 C9 H9A 109.4 . . ?
O3 C9 H9B 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.2 . . ?
O3 C10 C11 111.88(11) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
N1 C11 C10 109.15(11) . . ?
N1 C11 H11A 109.9 . . ?
N1 C11 H11B 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
N2 C12 H12A 109.6 . . ?
N2 C12 H12B 109.6 . . ?
N2 C12 C13 110.45(10) . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C14 C13 C12 121.03(12) . . ?
C18 C13 C12 120.60(12) . . ?
C18 C13 C14 118.36(12) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.79(12) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.21(12) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.56(13) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.25(13) . . ?
C18 C17 H17 119.9 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.81(13) . . ?
C17 C18 H18 119.6 . . ?
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 1.2357(16) . ?
O2 H2 0.99(2) . ?
O2 C3 1.4141(15) . ?
O3 C9 1.4275(17) . ?
O3 C10 1.4314(16) . ?
N1 C1 1.3534(16) . ?
N1 C8 1.4606(16) . ?
N1 C11 1.4606(16) . ?
N2 H2A 0.925(18) . ?
N2 C4 1.4653(16) . ?
N2 C12 1.4746(16) . ?
C1 C2 1.5098(17) . ?
C2 C3 1.5452(17) . ?
C2 C6 1.5636(17) . ?
C2 C7 1.5515(17) . ?
C3 H3 0.980(15) . ?
C3 C4 1.5803(17) . ?
C4 H4 1.011(15) . ?
C4 C5 1.5381(18) . ?
C5 H5 0.960(17) . ?
C5 C6 1.5491(18) . ?
C5 C7 1.5477(18) . ?
C6 H6A 0.953(16) . ?
C6 H6B 0.955(16) . ?
C7 H7A 1.023(16) . ?
C7 H7B 1.012(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.515(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5239(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5084(18) . ?
C13 C14 1.3963(18) . ?
C13 C18 1.3936(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.3861(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.384(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.388(2) . ?
C18 H18 0.9500 . ?
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 C1 C2 C3 94.16(14) . . . . ?
O1 C1 C2 C6 -130.46(13) . . . . ?
O1 C1 C2 C7 -23.76(17) . . . . ?
O2 C3 C4 N2 -5.02(14) . . . . ?
O2 C3 C4 C5 119.45(11) . . . . ?
O3 C10 C11 N1 55.48(14) . . . . ?
N1 C1 C2 C3 -86.34(15) . . . . ?
N1 C1 C2 C6 49.04(18) . . . . ?
N1 C1 C2 C7 155.74(12) . . . . ?
N1 C8 C9 O3 -57.69(15) . . . . ?
N2 C4 C5 C6 74.49(13) . . . . ?
N2 C4 C5 C7 163.58(11) . . . . ?
N2 C12 C13 C14 -70.01(16) . . . . ?
N2 C12 C13 C18 108.84(14) . . . . ?
C1 N1 C8 C9 -119.77(13) . . . . ?
C1 N1 C11 C10 120.80(14) . . . . ?
C1 C2 C3 O2 67.89(14) . . . . ?
C1 C2 C3 C4 -172.04(10) . . . . ?
C1 C2 C6 C5 154.43(12) . . . . ?
C1 C2 C7 C5 -163.86(11) . . . . ?
C2 C3 C4 N2 -123.81(11) . . . . ?
C2 C3 C4 C5 0.66(11) . . . . ?
C3 C2 C6 C5 -65.28(10) . . . . ?
C3 C2 C7 C5 68.76(10) . . . . ?
C3 C4 C5 C6 -44.69(11) . . . . ?
C3 C4 C5 C7 44.40(11) . . . . ?
C4 N2 C12 C13 -175.17(11) . . . . ?
C4 C5 C6 C2 66.00(10) . . . . ?
C4 C5 C7 C2 -68.64(10) . . . . ?
C6 C2 C3 O2 -77.15(12) . . . . ?
C6 C2 C3 C4 42.92(11) . . . . ?
C6 C2 C7 C5 -33.63(9) . . . . ?
C6 C5 C7 C2 33.97(9) . . . . ?
C7 C2 C3 O2 -165.42(10) . . . . ?
C7 C2 C3 C4 -45.34(11) . . . . ?
C7 C2 C6 C5 33.63(9) . . . . ?
C7 C5 C6 C2 -33.70(9) . . . . ?
C8 N1 C1 O1 0.32(19) . . . . ?
C8 N1 C1 C2 -179.16(11) . . . . ?
C8 N1 C11 C10 -55.07(14) . . . . ?
C9 O3 C10 C11 -58.00(15) . . . . ?
C10 O3 C9 C8 58.85(15) . . . . ?
C11 N1 C1 O1 -175.26(12) . . . . ?
C11 N1 C1 C2 5.3(2) . . . . ?
C11 N1 C8 C9 56.46(15) . . . . ?
C12 N2 C4 C3 169.10(10) . . . . ?
C12 N2 C4 C5 56.28(15) . . . . ?
C12 C13 C14 C15 178.99(12) . . . . ?
C12 C13 C18 C17 179.89(12) . . . . ?
C13 C14 C15 C16 1.10(19) . . . . ?
C14 C13 C18 C17 -1.23(19) . . . . ?
C14 C15 C16 C17 -1.22(19) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 1.1(2) . . . . ?
C18 C13 C14 C15 0.12(19) . . . . ?
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
2.5470 -7.3187 -2.7940 0.4179 0.8768 -0.2378
-2.4955 7.3292 2.7924 -0.4174 -0.8757 0.2428
-8.0085 -3.5119 4.8478 0.3809 -0.2933 -0.8769
4.0856 4.2956 -7.9815 -0.7678 0.2705 0.5808
5.6959 -1.3097 8.8377 0.8760 -0.2103 0.4340
-4.3548 2.9582 -8.9183 -0.9672 0.1264 -0.2202
