#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:45:31 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281600 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/91/7159173.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_7159173
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         'C10 H10 Cl N O2'
_chemical_formula_sum            'C10 H10 Cl N O2'
_chemical_formula_weight         211.64
_chemical_name_systematic        (S)-3-(4-chlorophenyl)-4-methyloxazolidin-2-one
_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   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dgqqb
_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                 93.371(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.53040(10)
_cell_length_b                   8.5314(2)
_cell_length_c                   10.1412(2)
_cell_measurement_reflns_used    3147
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7840
_cell_measurement_theta_min      4.3660
_cell_volume                     477.655(17)
_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 0.999
_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    -57.00 -32.00   0.50    3.20    --  -35.49  73.00  -9.00   50
  2  ω      5.00  31.00   0.50    3.20    --  -35.49  73.00  -9.00   52
  3  ω    120.00 153.00   0.50    9.43    --  100.00  73.00  -9.00   66
  4  ω     40.00 123.00   0.50    9.43    --  100.00 -73.00-138.00  166
  5  ω    -95.00 -49.00   0.50    3.20    --  -35.49 138.00 -30.00   92
  6  ω    -45.00 -16.00   0.50    3.20    --  -35.49 138.00 -30.00   58
  7  ω    -32.00   2.00   0.50    3.20    --   35.49 -65.00 120.00   68
  8  ω     24.00  53.00   0.50    3.20    --   35.49 -43.00 -60.00   58
  9  ω    -21.00  21.00   0.50    3.20    --   35.49 -43.00 -60.00   84
 10  ω     26.00  59.00   0.50    3.20    --   35.49 -89.00-150.00   66
 11  ω    -28.00  -1.00   0.50    3.20    --   35.49 -73.00-138.00   54
 12  ω    -25.00  17.00   0.50    3.20    --   35.49 -89.00-150.00   84
 13  ω      6.00  55.00   0.50    3.20    --   35.49 -65.00 120.00   98
 14  ω      3.00  28.00   0.50    3.20    --   35.49-104.00 150.00   50
 15  ω     39.00  64.00   0.50    3.20    --   35.49 -73.00-138.00   50
 16  ω     39.00  89.00   0.50    3.20    --   35.49-138.00 -90.00  100
 17  ω    118.00 144.00   0.50    9.43    --  100.00  37.00 120.00   52
 18  ω     81.00 115.00   0.50    9.43    --  100.00  37.00 120.00   68
 19  ω     36.00  80.00   0.50    9.43    --  100.00 -45.00  60.00   88
 20  ω     96.00 123.00   0.50    9.43    --  100.00  77.00 120.00   54
 21  ω     43.00  69.00   0.50    9.43    --  100.00-125.00-120.00   52
 22  ω     81.00 125.00   0.50    9.43    --  100.00-149.00  90.00   88
 23  ω    110.00 135.00   0.50    9.43    --  100.00  61.00 -90.00   50
 24  ω    124.00 157.00   0.50    9.43    --  100.00 149.00-180.00   66
 25  ω     33.00 117.00   0.50    9.43    --  100.00 -45.00-150.00  168
 26  ω     87.00 120.00   0.50    9.43    --  100.00 149.00-180.00   66
 27  ω     78.00 156.00   0.50    9.43    --  100.00  53.00-120.00  156
 28  ω     75.00 112.00   0.50    9.43    --  100.00-125.00-120.00   74
 29  ω     83.00 147.00   0.50    9.43    --  100.00  77.00 -30.00  128
 30  ω     74.00 116.00   0.50    9.43    --  100.00  69.00   0.00   84
 31  ω    131.00 156.00   0.50    9.43    --  100.00  69.00   0.00   50
 32  ω     88.00 126.00   0.50    9.43    --  100.00 107.00-120.00   76
 33  ω     88.00 118.00   0.50    9.43    --  100.00 -45.00  60.00   60
 34  ω     87.00 147.00   0.50    9.43    --  100.00  91.00 -60.00  120
 35  ω    -27.00  -1.00   0.50    3.20    --  -35.49  73.00  -9.00   52
 36  ω     -7.00  31.00   0.50    3.20    --  -35.49  54.00 -90.00   76
 37  ω     41.00 103.00   0.50    3.20    --   35.49  43.00  60.00  124
 38  ω    -35.00  -9.00   0.50    3.20    --   35.49 -21.00-150.00   52
 39  ω     69.00 101.00   0.50    3.20    --   35.49  32.00 150.00   64
 40  ω     29.00  55.00   0.50    3.20    --   35.49-138.00  60.00   52
 41  ω     23.00  50.00   0.50    3.20    --   35.49 -21.00-150.00   54
 42  ω     47.00 102.00   0.50    3.20    --   35.49  65.00  90.00  110
 43  ω     28.00  61.00   0.50    3.20    --   35.49  32.00 150.00   66
 44  ω     79.00 157.00   0.50    9.43    --  100.00  53.00  30.00  156
 45  ω     74.00 102.00   0.50    9.43    --  100.00  69.00  60.00   56
 46  ω    119.00 145.00   0.50    9.43    --  100.00  69.00 120.00   52
 47  ω    117.00 143.00   0.50    9.43    --  100.00  69.00  60.00   52
 48  ω     39.00  65.00   0.50    9.43    --  100.00-125.00   0.00   52
 49  ω     82.00 108.00   0.50    9.43    --  100.00-125.00   0.00   52
 50  ω    111.00 147.00   0.50    9.43    --  100.00  45.00  90.00   72
 51  ω     30.00  55.00   0.50    9.43    --  100.00 -30.00-180.00   50
 52  ω     79.00 105.00   0.50    9.43    --  100.00  69.00 120.00   52
 53  ω    116.00 141.00   0.50    9.43    --  100.00 107.00 120.00   50
 54  ω    130.00 155.00   0.50    9.43    --  100.00  -7.00 150.00   50
 55  ω     69.00 120.00   0.50    9.43    --  100.00 -30.00-180.00  102
 56  ω     75.00 107.00   0.50    9.43    --  100.00-107.00-120.00   64
 57  ω     81.00 111.00   0.50    9.43    --  100.00 -77.00  30.00   60
 58  ω     87.00 113.00   0.50    9.43    --  100.00  45.00 150.00   52
 59  ω    116.00 144.00   0.50    9.43    --  100.00  45.00 150.00   56
 60  ω    113.00 152.00   0.50    9.43    --  100.00  53.00  60.00   78
 61  ω     73.00  99.00   0.50    9.43    --  100.00  69.00  90.00   52
 62  ω     29.00  67.00   0.50    9.43    --  100.00 -91.00  30.00   76
 63  ω     81.00 106.00   0.50    9.43    --  100.00 -91.00  30.00   50
 64  ω     27.00  73.00   0.50    9.43    --  100.00-107.00   0.00   92
 65  ω     35.00  61.00   0.50    9.43    --  100.00-125.00 -60.00   52
 66  ω     67.00  93.00   0.50    9.43    --  100.00-125.00 -60.00   52
 67  ω     49.00  75.00   0.50    9.43    --  100.00 -77.00  30.00   52
 68  ω     66.00 116.00   0.50    9.43    --  100.00 -61.00  30.00  100
 69  ω     20.00  46.00   0.50    9.43    --  100.00  -7.00 150.00   52
 70  ω     26.00  68.00   0.50    9.43    --  100.00-107.00-120.00   84
 71  ω     81.00 107.00   0.50    9.43    --  100.00  53.00 120.00   52
 72  ω     80.00 105.00   0.50    9.43    --  100.00  45.00  90.00   50
 73  ω     98.00 145.00   0.50    9.43    --  100.00  37.00  60.00   94
;
_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      0.0749331000
_diffrn_orient_matrix_UB_12      -0.0395502000
_diffrn_orient_matrix_UB_13      -0.1400594000
_diffrn_orient_matrix_UB_21      -0.1462552000
_diffrn_orient_matrix_UB_22      0.1415174000
_diffrn_orient_matrix_UB_23      -0.0552728000
_diffrn_orient_matrix_UB_31      0.2256245000
_diffrn_orient_matrix_UB_32      0.1049519000
_diffrn_orient_matrix_UB_33      0.0217378000
_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  0.0112
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3560
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        64.867
_diffrn_reflns_theta_max         64.867
_diffrn_reflns_theta_min         4.367
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.319
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84962
_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    1.472
_exptl_crystal_description       prism
_exptl_crystal_F_000             220
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOAc'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.014(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1613
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0199
_refine_ls_R_factor_gt           0.0197
_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)+(0.0312P)²+0.0971P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0523
_reflns_Friedel_coverage         0.854
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1591
_reflns_number_total             1613
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02122f2.cif
_cod_data_source_block           evk-557_auto
_cod_depositor_comments
'Adding full bibliography for 7159171--7159173.cif.'
_cod_database_code               7159173
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C10 H10 Cl 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   0.754
_shelx_estimated_absorpt_t_min   0.619
_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:
 C2(H2), C5(H5), C6(H6), C3(H3)
1.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.789
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
Cl14 Cl 1.06794(8) 0.45962(6) 0.67580(4) 0.02749(16) Uani 1 1 d . . . . .
O9 O 0.1381(3) 0.40392(17) 0.03865(15) 0.0236(4) Uani 1 1 d . . . . .
O12 O 0.3573(3) 0.22414(19) 0.15566(15) 0.0250(4) Uani 1 1 d . . . . .
N7 N 0.3826(3) 0.4899(2) 0.20436(16) 0.0205(4) Uani 1 1 d . . . . .
C8 C 0.3011(4) 0.3602(3) 0.1367(2) 0.0217(5) Uani 1 1 d . . . . .
C1 C 0.5449(3) 0.4815(3) 0.31851(18) 0.0190(4) Uani 1 1 d . . . . .
C2 C 0.4956(4) 0.5643(3) 0.4322(2) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.3527 0.6259 0.4338 0.025 Uiso 1 1 calc R U . . .
C5 C 0.9140(4) 0.3835(3) 0.4261(2) 0.0234(4) Uani 1 1 d . . . . .
H5 H 1.0567 0.3217 0.4247 0.028 Uiso 1 1 calc R U . . .
C6 C 0.7535(4) 0.3914(3) 0.3155(2) 0.0218(4) Uani 1 1 d . . . . .
H6 H 0.7866 0.3351 0.2378 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6549(4) 0.5570(3) 0.5432(2) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.6217 0.6126 0.6213 0.026 Uiso 1 1 calc R U . . .
C4 C 0.8630(3) 0.4671(3) 0.53822(18) 0.0212(4) Uani 1 1 d . . . . .
C13 C 0.3975(4) 0.7761(3) 0.1558(2) 0.0252(5) Uani 1 1 d . . . . .
H13A H 0.4520 0.8096 0.2451 0.038 Uiso 1 1 calc R U . . .
H13B H 0.3021 0.8600 0.1121 0.038 Uiso 1 1 calc R U . . .
H13C H 0.5386 0.7531 0.1050 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2432(4) 0.6307(3) 0.1639(2) 0.0222(5) Uani 1 1 d . . . . .
H11 H 0.1102 0.6487 0.2248 0.027 Uiso 1 1 calc R U . . .
C10 C 0.1384(4) 0.5739(3) 0.0292(2) 0.0275(5) Uani 1 1 d . . . . .
H10A H -0.0282 0.6142 0.0111 0.033 Uiso 1 1 calc R U . . .
H10B H 0.2403 0.6092 -0.0422 0.033 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'
Cl Cl 0.3639 0.7018 '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 108.66(18) . . ?
C8 N7 C1 122.80(18) . . ?
C8 N7 C11 111.68(17) . . ?
C1 N7 C11 124.18(17) . . ?
O9 C8 N7 109.38(19) . . ?
O12 C8 O9 122.2(2) . . ?
O12 C8 N7 128.4(2) . . ?
C2 C1 N7 120.18(18) . . ?
C6 C1 N7 119.64(17) . . ?
C6 C1 C2 120.17(18) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.16(19) . . ?
C3 C2 H2 119.9 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.09(19) . . ?
C1 C6 C5 120.06(19) . . ?
C1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.90(19) . . ?
C4 C3 H3 120.5 . . ?
C5 C4 Cl14 118.90(16) . . ?
C5 C4 C3 121.61(18) . . ?
C3 C4 Cl14 119.49(16) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
N7 C11 C13 113.40(18) . . ?
N7 C11 H11 110.2 . . ?
N7 C11 C10 98.92(17) . . ?
C13 C11 H11 110.2 . . ?
C13 C11 C10 113.38(19) . . ?
C10 C11 H11 110.2 . . ?
O9 C10 C11 104.98(18) . . ?
O9 C10 H10A 110.8 . . ?
O9 C10 H10B 110.8 . . ?
C11 C10 H10A 110.8 . . ?
C11 C10 H10B 110.8 . . ?
H10A C10 H10B 108.8 . . ?
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
Cl14 C4 1.7462(18) . ?
O9 C8 1.354(3) . ?
O9 C10 1.454(3) . ?
O12 C8 1.214(3) . ?
N7 C8 1.364(3) . ?
N7 C1 1.424(2) . ?
N7 C11 1.472(3) . ?
C1 C2 1.392(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C5 C4 1.386(3) . ?
C6 H6 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C11 1.511(3) . ?
C11 H11 1.0000 . ?
C11 C10 1.531(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
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 C2 C3 -179.53(19) . . . . ?
N7 C1 C6 C5 179.47(19) . . . . ?
N7 C11 C10 O9 24.3(2) . . . . ?
C8 O9 C10 C11 -21.5(2) . . . . ?
C8 N7 C1 C2 -131.4(2) . . . . ?
C8 N7 C1 C6 49.2(3) . . . . ?
C8 N7 C11 C13 -141.01(18) . . . . ?
C8 N7 C11 C10 -20.6(2) . . . . ?
C1 N7 C8 O9 176.05(16) . . . . ?
C1 N7 C8 O12 -4.0(3) . . . . ?
C1 N7 C11 C13 51.9(3) . . . . ?
C1 N7 C11 C10 172.25(17) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
C2 C3 C4 Cl14 178.79(17) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C5 C4 Cl14 -178.85(17) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C13 C11 C10 O9 144.6(2) . . . . ?
C11 N7 C8 O9 8.7(2) . . . . ?
C11 N7 C8 O12 -171.3(2) . . . . ?
C11 N7 C1 C2 34.3(3) . . . . ?
C11 N7 C1 C6 -145.1(2) . . . . ?
C10 O9 C8 O12 -171.4(2) . . . . ?
C10 O9 C8 N7 8.6(2) . . . . ?
