#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:45:31 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281600 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/91/7159172.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_7159172
loop_
_publ_author_name
'Podrezova, Ekaterina V.'
'Okhina, Alina A.'
'Rogachev, Artem D.'
'Baykov, Sergey V.'
'Kirschning, Andreas'
'Yusubov, Mekhman S.'
'Soldatova, Natalia S.'
'Postnikov, Pavel S.'
_publ_section_title
;
 Ligand-free Ullmann-type arylation of oxazolidinones by diaryliodonium
 salts.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1952
_journal_page_last               1957
_journal_paper_doi               10.1039/d2ob02122f
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H17 N O2'
_chemical_formula_sum            'C13 H17 N O2'
_chemical_formula_weight         219.27
_chemical_name_systematic        (S)-4-(tert-butyl)-3-phenyloxazolidin-2-one
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqp9
_audit_creation_date             2022-11-07
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-11-10 deposited with the CCDC.	2023-02-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2495(2)
_cell_length_b                   12.5730(3)
_cell_length_c                   15.1106(5)
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.9380
_cell_measurement_theta_min      4.5540
_cell_volume                     1187.31(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -106.00 -56.00   0.50    0.84    --  -35.49-163.00  -8.00  100
  2  ω    -58.00   9.00   0.50    0.84    --  -35.49  52.00  -1.00  134
  3  ω    -72.00 -47.00   0.50    0.84    --  -35.49 116.00-130.00   50
  4  ω     32.00  57.00   0.50    0.84    --   35.49-163.00  -8.00   50
  5  ω     60.00  94.00   0.50    0.84    --   35.49  52.00  -1.00   68
  6  ω     81.00 106.00   0.50    0.84    --   35.49-163.00  -8.00   50
  7  ω     23.00  54.00   0.50    0.84    --   35.49  52.00  -1.00   62
  8  ω      8.00  45.00   0.50    0.84    --   35.49  69.00 154.00   74
  9  ω     89.00 115.00   0.50    3.36    --  100.00 163.00  18.00   52
 10  ω     73.00 140.00   0.50    3.36    --  100.00  69.00 154.00  134
 11  ω     77.00 128.00   0.50    3.36    --  100.00  52.00  -1.00  102
 12  ω     60.00  86.00   0.50    3.36    --  100.00 -69.00  22.00   52
 13  ω     77.00 112.00   0.50    3.36    --  100.00 -52.00-146.00   70
 14  ω     65.00  91.00   0.50    3.36    --  100.00-116.00 141.00   52
 15  ω    -73.00  -6.00   0.50    0.84    --  -35.49 104.00   0.00  134
 16  ω    -38.00  -8.00   0.50    0.84    --  -35.49 116.00-130.00   60
 17  ω    -79.00 -54.00   0.50    0.84    --  -35.49 -69.00  22.00   50
 18  ω     23.00  48.00   0.50    0.84    --   35.49-138.00-120.00   50
 19  ω      4.00  42.00   0.50    0.84    --   35.49-116.00 141.00   76
 20  ω     83.00 121.00   0.50    3.36    --  100.00  77.00 120.00   76
 21  ω    110.00 156.00   0.50    3.36    --  100.00 107.00-180.00   92
 22  ω     90.00 149.00   0.50    3.36    --  100.00  91.00  90.00  118
 23  ω     55.00 107.00   0.50    3.36    --  100.00 -45.00-180.00  104
 24  ω     88.00 156.00   0.50    3.36    --  100.00 107.00-120.00  136
 25  ω     85.00 143.00   0.50    3.36    --  100.00  91.00 -90.00  116
 26  ω    127.00 154.00   0.50    3.36    --  100.00  77.00 120.00   54
 27  ω     86.00 157.00   0.50    3.36    --  100.00  37.00  60.00  142
 28  ω    -33.00  -7.00   0.50    0.84    --   35.49 -69.00  22.00   52
 29  ω      0.00  26.00   0.50    0.84    --  -35.49  32.00-150.00   52
 30  ω   -107.00 -81.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 31  ω    -43.00 -17.00   0.50    0.84    --  -35.49 -32.00 120.00   52
 32  ω    -49.00  -9.00   0.50    0.84    --  -35.49  32.00-150.00   80
 33  ω     61.00 105.00   0.50    0.84    --   35.49  43.00 150.00   88
 34  ω     53.00 103.00   0.50    0.84    --   35.49  65.00 -90.00  100
 35  ω     -9.00  27.00   0.50    0.84    --   35.49 -32.00   0.00   72
 36  ω     17.00  49.00   0.50    0.84    --   35.49  43.00 150.00   64
 37  ω     18.00  44.00   0.50    0.84    --   35.49  43.00 -90.00   52
 38  ω     75.00 105.00   0.50    0.84    --   35.49  43.00 -90.00   60
 39  ω    -40.00  10.00   0.50    0.84    --   35.49 -21.00  30.00  100
 40  ω     24.00  50.00   0.50    0.84    --   35.49 -69.00  22.00   52
 41  ω     12.00  37.00   0.50    0.84    --   35.49  65.00 -90.00   50
 42  ω     37.00  63.00   0.50    0.84    --   35.49 -21.00  30.00   52
 43  ω     13.00  43.00   0.50    0.84    --   35.49  54.00 -60.00   60
 44  ω     40.00  78.00   0.50    3.36    --  100.00 -30.00-120.00   76
 45  ω     31.00  57.00   0.50    3.36    --  100.00-107.00  90.00   52
 46  ω     77.00 103.00   0.50    3.36    --  100.00 -91.00-150.00   52
 47  ω    132.00 157.00   0.50    3.36    --  100.00  69.00 -90.00   50
 48  ω     26.00  83.00   0.50    3.36    --  100.00-107.00  60.00  114
 49  ω     75.00 101.00   0.50    3.36    --  100.00  61.00 -90.00   52
 50  ω     25.00  99.00   0.50    3.36    --  100.00 -22.00 150.00  148
 51  ω    125.00 151.00   0.50    3.36    --  100.00 107.00-150.00   52
 52  ω     90.00 116.00   0.50    3.36    --  100.00 107.00 -60.00   52
 53  ω     74.00 100.00   0.50    3.36    --  100.00  69.00 -90.00   52
 54  ω     56.00  82.00   0.50    3.36    --  100.00 -53.00  30.00   52
 55  ω    122.00 149.00   0.50    3.36    --  100.00  30.00 150.00   54
 56  ω     86.00 112.00   0.50    3.36    --  100.00-125.00-180.00   52
 57  ω     75.00 107.00   0.50    3.36    --  100.00-107.00  90.00   64
 58  ω     77.00 102.00   0.50    3.36    --  100.00  53.00 -90.00   50
 59  ω     79.00 104.00   0.50    3.36    --  100.00  45.00  90.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0430028000
_diffrn_orient_matrix_UB_12      -0.0035783000
_diffrn_orient_matrix_UB_13      0.1004175000
_diffrn_orient_matrix_UB_21      0.1506175000
_diffrn_orient_matrix_UB_22      -0.0963471000
_diffrn_orient_matrix_UB_23      0.0086642000
_diffrn_orient_matrix_UB_31      0.1903278000
_diffrn_orient_matrix_UB_32      0.0755195000
_diffrn_orient_matrix_UB_33      0.0157136000
_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  0.0553
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6810
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        64.985
_diffrn_reflns_theta_max         64.985
_diffrn_reflns_theta_min         4.575
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       prism
_exptl_crystal_F_000             472
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 653 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1980
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0405
_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)+(0.0499P)²+0.0574P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0969
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.942
_reflns_number_gt                1792
_reflns_number_total             1980
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02122f2.cif
_cod_data_source_block           evk-548_auto
_cod_depositor_comments
'Adding full bibliography for 7159171--7159173.cif.'
_cod_database_code               7159172
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C13 H17 N O2 '
_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   0.955
_shelx_estimated_absorpt_t_min   0.931
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C11(H11)
1.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
1.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2), C3(H3), C4(H4)
1.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 1.561
_oxdiff_exptl_absorpt_empirical_full_min 0.257
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'
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
O9 O 0.9018(3) 0.36077(13) 0.53808(12) 0.0281(4) Uani 1 1 d . . . . .
O12 O 1.0899(3) 0.45228(14) 0.63876(12) 0.0286(4) Uani 1 1 d . . . . .
N7 N 0.7385(3) 0.49542(16) 0.60510(12) 0.0197(4) Uani 1 1 d . . . . .
C1 C 0.7085(4) 0.57931(18) 0.66735(14) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.8724(4) 0.65097(19) 0.68456(16) 0.0224(5) Uani 1 1 d . . . . .
H6 H 1.0075 0.6428 0.6566 0.027 Uiso 1 1 calc R U . . .
C8 C 0.9241(4) 0.43930(19) 0.59872(16) 0.0229(5) Uani 1 1 d . . . . .
C5 C 0.8381(4) 0.7345(2) 0.74275(16) 0.0245(6) Uani 1 1 d . . . . .
H5 H 0.9507 0.7831 0.7550 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5791(4) 0.46097(18) 0.53834(15) 0.0212(5) Uani 1 1 d . . . . .
H11 H 0.4392 0.4472 0.5683 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5109(4) 0.59023(19) 0.70952(15) 0.0215(5) Uani 1 1 d . . . . .
H2 H 0.3998 0.5402 0.6992 0.026 Uiso 1 1 calc R U . . .
C3 C 0.4792(5) 0.6751(2) 0.76667(16) 0.0272(6) Uani 1 1 d . . . . .
H3 H 0.3444 0.6836 0.7949 0.033 Uiso 1 1 calc R U . . .
C13 C 0.5447(4) 0.5409(2) 0.46176(15) 0.0247(5) Uani 1 1 d . . . . .
C4 C 0.6408(4) 0.7476(2) 0.78308(16) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.6167 0.8060 0.8217 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6799(4) 0.3547(2) 0.51108(18) 0.0272(6) Uani 1 1 d . . . . .
H10A H 0.6071 0.2948 0.5411 0.033 Uiso 1 1 calc R U . . .
H10B H 0.6690 0.3444 0.4463 0.033 Uiso 1 1 calc R U . . .
C15 C 0.4419(4) 0.6434(2) 0.49648(16) 0.0283(6) Uani 1 1 d . . . . .
H15A H 0.3124 0.6258 0.5300 0.042 Uiso 1 1 calc R U . . .
H15B H 0.4043 0.6894 0.4465 0.042 Uiso 1 1 calc R U . . .
H15C H 0.5432 0.6805 0.5352 0.042 Uiso 1 1 calc R U . . .
C14 C 0.3869(5) 0.4892(2) 0.39675(18) 0.0336(6) Uani 1 1 d . . . . .
H14A H 0.4549 0.4276 0.3687 0.050 Uiso 1 1 calc R U . . .
H14B H 0.3464 0.5410 0.3512 0.050 Uiso 1 1 calc R U . . .
H14C H 0.2589 0.4661 0.4288 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7549(4) 0.5672(2) 0.41487(18) 0.0318(6) Uani 1 1 d . . . . .
H16A H 0.8537 0.6005 0.4569 0.048 Uiso 1 1 calc R U . . .
H16B H 0.7269 0.6163 0.3659 0.048 Uiso 1 1 calc R U . . .
H16C H 0.8188 0.5017 0.3918 0.048 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_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv-2022-xnmf7 2022
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
C8 O9 C10 109.13(19) . . ?
C1 N7 C11 125.3(2) . . ?
C8 N7 C1 122.8(2) . . ?
C8 N7 C11 111.89(19) . . ?
C6 C1 N7 120.5(2) . . ?
C6 C1 C2 120.2(2) . . ?
C2 C1 N7 119.3(2) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
O9 C8 N7 109.8(2) . . ?
O12 C8 O9 121.6(2) . . ?
O12 C8 N7 128.6(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
N7 C11 H11 109.3 . . ?
N7 C11 C13 114.35(19) . . ?
N7 C11 C10 99.29(19) . . ?
C13 C11 H11 109.3 . . ?
C10 C11 H11 109.3 . . ?
C10 C11 C13 115.0(2) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C15 C13 C11 110.39(19) . . ?
C15 C13 C14 107.8(2) . . ?
C14 C13 C11 107.0(2) . . ?
C16 C13 C11 111.6(2) . . ?
C16 C13 C15 109.7(2) . . ?
C16 C13 C14 110.3(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.5(2) . . ?
C3 C4 H4 120.2 . . ?
O9 C10 C11 105.77(19) . . ?
O9 C10 H10A 110.6 . . ?
O9 C10 H10B 110.6 . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
H10A C10 H10B 108.7 . . ?
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 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 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 . . ?
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
O9 C8 1.354(3) . ?
O9 C10 1.447(3) . ?
O12 C8 1.211(3) . ?
N7 C1 1.425(3) . ?
N7 C8 1.361(3) . ?
N7 C11 1.482(3) . ?
C1 C6 1.389(4) . ?
C1 C2 1.396(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(4) . ?
C11 H11 1.0000 . ?
C11 C13 1.548(3) . ?
C11 C10 1.534(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(4) . ?
C13 C15 1.533(3) . ?
C13 C14 1.536(4) . ?
C13 C16 1.528(4) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
N7 C1 C6 C5 177.5(2) . . . . ?
N7 C1 C2 C3 -176.8(2) . . . . ?
N7 C11 C13 C15 -66.5(3) . . . . ?
N7 C11 C13 C14 176.5(2) . . . . ?
N7 C11 C13 C16 55.7(3) . . . . ?
N7 C11 C10 O9 -19.6(2) . . . . ?
C1 N7 C8 O9 176.2(2) . . . . ?
C1 N7 C8 O12 -3.6(4) . . . . ?
C1 N7 C11 C13 70.9(3) . . . . ?
C1 N7 C11 C10 -166.2(2) . . . . ?
C1 C6 C5 C4 -0.7(4) . . . . ?
C1 C2 C3 C4 -0.9(4) . . . . ?
C6 C1 C2 C3 1.8(3) . . . . ?
C6 C5 C4 C3 1.6(4) . . . . ?
C8 O9 C10 C11 18.2(3) . . . . ?
C8 N7 C1 C6 40.2(3) . . . . ?
C8 N7 C1 C2 -141.3(2) . . . . ?
C8 N7 C11 C13 -107.1(2) . . . . ?
C8 N7 C11 C10 15.8(2) . . . . ?
C11 N7 C1 C6 -137.6(2) . . . . ?
C11 N7 C1 C2 41.0(3) . . . . ?
C11 N7 C8 O9 -5.8(3) . . . . ?
C11 N7 C8 O12 174.4(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C13 C11 C10 O9 102.9(2) . . . . ?
C10 O9 C8 O12 171.6(2) . . . . ?
C10 O9 C8 N7 -8.2(3) . . . . ?
C10 C11 C13 C15 179.5(2) . . . . ?
C10 C11 C13 C14 62.5(3) . . . . ?
C10 C11 C13 C16 -58.2(3) . . . . ?
