#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/09/2220972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220972
loop_
_publ_author_name
'Palamarchuk, G. V.'
'Borisov, O. V.'
'Kovalenko, S. S.'
'Chernykh, V. P.'
'Kovalenko, S. M.'
'Baumer, V. N.'
'Shishkin, O. V.'
_publ_section_title
1-(8-Bromo-2-methyl-4-thioxo-3,4,5,6-tetrahydro-2H-2,6-methano-1,3-benzoxazocin-11-yl)ethanone
_journal_coeditor_code           BG2221
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o461
_journal_paper_doi               10.1107/S160053680900347X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H14 Br N O2 S'
_chemical_formula_moiety         'C14 H14 Br N O2 S'
_chemical_formula_sum            'C14 H14 Br N O2 S'
_chemical_formula_weight         340.23
_chemical_name_systematic
;
1-(8-Bromo-2-methyl-4-thioxo-3,4,5,6-tetrahydro-2H-2,6-methano-1,3-
benzoxazocin-11-yl)ethanone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                98.67(5)
_cell_angle_beta                 99.09(5)
_cell_angle_gamma                101.81(5)
_cell_formula_units_Z            4
_cell_length_a                   8.213(5)
_cell_length_b                   11.625(7)
_cell_length_c                   15.156(10)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      10
_cell_volume                     1373.3(16)
_computing_cell_refinement       'P3 (Siemens, 1991)'
_computing_data_collection       'P3 (Siemens, 1991)'
_computing_data_reduction        'XDISK and XPREP (Siemens, 1991)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Siemens P3/PC'
_diffrn_measurement_method       2θ/θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7869
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.07
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    3.142
_exptl_absorpt_correction_T_max  0.8550
_exptl_absorpt_correction_T_min  0.6112
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(XPREP; Siemens, 1991)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.427
_refine_ls_extinction_coef       0.0026(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4773
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0521
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0597P)²+0.9457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1180
_reflns_number_gt                3383
_reflns_number_total             4773
_reflns_threshold_expression     I>2/s(I)
_cod_data_source_file            bg2221.cif
_cod_data_source_block           I
_cod_original_cell_volume        1373.1(15)
_cod_database_code               2220972
_cod_database_fobs_code          2220972
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.62044(6) 0.83270(4) 0.58068(4) 0.05907(14) Uani d . 1 . .
S S1A 0.17210(13) 0.30146(10) 0.67922(7) 0.0413(3) Uani d . 1 . .
C C1A 0.6441(5) 0.5017(3) 0.7900(2) 0.0269(8) Uani d . 1 . .
H H1A 0.6925 0.5695 0.8406 0.032 Uiso calc R 1 . .
C C2A 0.6686(4) 0.5407(3) 0.7023(2) 0.0273(8) Uani d . 1 . .
C C3A 0.6433(5) 0.6509(3) 0.6851(2) 0.0295(9) Uani d . 1 . .
H H3A 0.6122 0.7024 0.7291 0.035 Uiso calc R 1 . .
C C4A 0.6641(5) 0.6833(3) 0.6045(3) 0.0346(9) Uani d . 1 . .
C C5A 0.7090(5) 0.6098(4) 0.5373(3) 0.0421(11) Uani d . 1 . .
H H5A 0.7218 0.6340 0.4825 0.050 Uiso calc R 1 . .
C C6A 0.7350(5) 0.4992(4) 0.5518(2) 0.0373(10) Uani d . 1 . .
H H6A 0.7678 0.4488 0.5077 0.045 Uiso calc R 1 . .
C C7A 0.7109(4) 0.4659(3) 0.6333(2) 0.0271(8) Uani d . 1 . .
O O8A 0.7374(3) 0.3533(2) 0.64432(16) 0.0299(6) Uani d . 1 . .
C C9A 0.6713(4) 0.3045(3) 0.7161(2) 0.0259(8) Uani d . 1 . .
N N10A 0.4847(4) 0.2771(2) 0.69181(19) 0.0284(7) Uani d . 1 . .
H H10A 0.4371 0.2105 0.6551 0.034 Uiso calc R 1 . .
C C11A 0.3799(5) 0.3432(3) 0.7199(2) 0.0302(9) Uani d . 1 . .
C C12A 0.4574(5) 0.4563(3) 0.7894(2) 0.0315(9) Uani d . 1 . .
H H12A 0.4436 0.4411 0.8493 0.038 Uiso calc R 1 . .
H H12B 0.3979 0.5175 0.7762 0.038 Uiso calc R 1 . .
C C13A 0.7290(4) 0.3964(3) 0.8053(2) 0.0264(8) Uani d . 1 . .
H H13A 0.6831 0.3599 0.8531 0.032 Uiso calc R 1 . .
C C14A 0.9203(5) 0.4390(3) 0.8362(2) 0.0307(9) Uani d . 1 . .
O O14A 1.0003(3) 0.5252(2) 0.8167(2) 0.0447(8) Uani d . 1 . .
C C15A 1.0060(6) 0.3680(4) 0.8959(3) 0.0531(13) Uani d . 1 . .
H H15A 1.1254 0.4039 0.9121 0.080 Uiso calc R 1 . .
H H15B 0.9881 0.2874 0.8637 0.080 Uiso calc R 1 . .
H H15C 0.9592 0.3675 0.9501 0.080 Uiso calc R 1 . .
C C16A 0.7249(5) 0.1878(3) 0.7156(3) 0.0370(10) Uani d . 1 . .
H H16A 0.6847 0.1382 0.6564 0.056 Uiso calc R 1 . .
H H16B 0.6777 0.1476 0.7599 0.056 Uiso calc R 1 . .
H H16C 0.8464 0.2035 0.7304 0.056 Uiso calc R 1 . .
Br Br1B 0.59308(7) 1.32613(4) 1.02809(3) 0.05332(14) Uani d . 1 . .
S S1B -0.10276(13) 0.80780(9) 0.93052(6) 0.0360(2) Uani d . 1 . .
C C1B 0.1321(4) 1.0087(3) 0.7679(2) 0.0230(8) Uani d . 1 . .
H H1AA 0.1125 1.0779 0.7416 0.028 Uiso calc R 1 . .
C C2B 0.3048(4) 1.0401(3) 0.8293(2) 0.0252(8) Uani d . 1 . .
C C3B 0.3636(5) 1.1495(3) 0.8877(2) 0.0278(9) Uani d . 1 . .
H H3AA 0.2963 1.2048 0.8891 0.033 Uiso calc R 1 . .
C C4B 0.5208(5) 1.1774(3) 0.9439(2) 0.0356(10) Uani d . 1 . .
C C5B 0.6249(4) 1.0974(3) 0.9440(2) 0.0320(9) Uani d . 1 . .
H H5AA 0.7312 1.1168 0.9820 0.038 Uiso calc R 1 . .
C C6B 0.5661(5) 0.9884(3) 0.8862(2) 0.0319(9) Uani d . 1 . .
H H6AA 0.6343 0.9337 0.8845 0.038 Uiso calc R 1 . .
C C7B 0.4067(4) 0.9585(3) 0.8304(2) 0.0224(8) Uani d . 1 . .
O O8B 0.3583(3) 0.84740(19) 0.77593(16) 0.0274(6) Uani d . 1 . .
C C9B 0.1825(4) 0.8068(3) 0.7368(2) 0.0271(8) Uani d . 1 . .
N N10B 0.0844(4) 0.7827(2) 0.8077(2) 0.0293(7) Uani d . 1 . .
H H10B 0.0821 0.7148 0.8240 0.035 Uiso calc R 1 . .
C C11B -0.0017(4) 0.8516(3) 0.8502(2) 0.0266(8) Uani d . 1 . .
C C12B -0.0047(4) 0.9703(3) 0.8219(2) 0.0271(8) Uani d . 1 . .
H H12C 0.0108 1.0312 0.8759 0.032 Uiso calc R 1 . .
H H12D -0.1150 0.9649 0.7852 0.032 Uiso calc R 1 . .
C C13B 0.1177(4) 0.9023(3) 0.6920(2) 0.0235(8) Uani d . 1 . .
H H13B -0.0029 0.8700 0.6653 0.028 Uiso calc R 1 . .
C C14B 0.2102(4) 0.9365(3) 0.6148(2) 0.0291(9) Uani d . 1 . .
O O14B 0.3348(4) 1.0153(2) 0.63118(17) 0.0438(8) Uani d . 1 . .
C C15B 0.1367(7) 0.8714(5) 0.5217(3) 0.0717(17) Uani d . 1 . .
H H15D 0.1654 0.9222 0.4793 0.108 Uiso calc R 1 . .
H H15F 0.0156 0.8478 0.5145 0.108 Uiso calc R 1 . .
H H15G 0.1811 0.8015 0.5102 0.108 Uiso calc R 1 . .
C C16B 0.1689(5) 0.6886(3) 0.6746(3) 0.0413(11) Uani d . 1 . .
H H16F 0.2055 0.6334 0.7100 0.062 Uiso calc R 1 . .
H H16G 0.2394 0.7013 0.6304 0.062 Uiso calc R 1 . .
H H16D 0.0532 0.6563 0.6439 0.062 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2A C1A C12A . . 110.6(3) ?
C2A C1A C13A . . 111.7(3) ?
C12A C1A C13A . . 106.3(3) ?
C2A C1A H1A . . 109.4 ?
C12A C1A H1A . . 109.4 ?
C13A C1A H1A . . 109.4 ?
C7A C2A C3A . . 117.5(3) ?
C7A C2A C1A . . 121.0(3) ?
C3A C2A C1A . . 121.5(3) ?
C4A C3A C2A . . 120.2(3) ?
C4A C3A H3A . . 119.9 ?
C2A C3A H3A . . 119.9 ?
C3A C4A C5A . . 121.9(4) ?
C3A C4A Br1A . . 119.5(3) ?
C5A C4A Br1A . . 118.5(3) ?
C4A C5A C6A . . 119.5(4) ?
C4A C5A H5A . . 120.2 ?
C6A C5A H5A . . 120.2 ?
C7A C6A C5A . . 118.2(4) ?
C7A C6A H6A . . 120.9 ?
C5A C6A H6A . . 120.9 ?
C6A C7A C2A . . 122.6(4) ?
C6A C7A O8A . . 116.1(3) ?
C2A C7A O8A . . 121.3(3) ?
C7A O8A C9A . . 116.4(3) ?
O8A C9A N10A . . 108.0(3) ?
O8A C9A C16A . . 105.3(3) ?
N10A C9A C16A . . 108.0(3) ?
O8A C9A C13A . . 110.2(3) ?
N10A C9A C13A . . 108.6(3) ?
C16A C9A C13A . . 116.5(3) ?
C11A N10A C9A . . 128.0(3) ?
C11A N10A H10A . . 116.0 ?
C9A N10A H10A . . 116.0 ?
N10A C11A C12A . . 117.6(3) ?
N10A C11A S1A . . 121.0(3) ?
C12A C11A S1A . . 121.4(3) ?
C11A C12A C1A . . 112.1(3) ?
C11A C12A H12A . . 109.2 ?
C1A C12A H12A . . 109.2 ?
C11A C12A H12B . . 109.2 ?
C1A C12A H12B . . 109.2 ?
H12A C12A H12B . . 107.9 ?
C14A C13A C9A . . 114.5(3) ?
C14A C13A C1A . . 111.9(3) ?
C9A C13A C1A . . 105.8(3) ?
C14A C13A H13A . . 108.1 ?
C9A C13A H13A . . 108.1 ?
C1A C13A H13A . . 108.1 ?
O14A C14A C15A . . 120.4(4) ?
O14A C14A C13A . . 122.8(3) ?
C15A C14A C13A . . 116.8(3) ?
C14A C15A H15A . . 109.5 ?
C14A C15A H15B . . 109.5 ?
H15A C15A H15B . . 109.5 ?
C14A C15A H15C . . 109.5 ?
H15A C15A H15C . . 109.5 ?
H15B C15A H15C . . 109.5 ?
C9A C16A H16A . . 109.5 ?
C9A C16A H16B . . 109.5 ?
H16A C16A H16B . . 109.5 ?
C9A C16A H16C . . 109.5 ?
H16A C16A H16C . . 109.5 ?
H16B C16A H16C . . 109.5 ?
C2B C1B C12B . . 109.8(3) ?
C2B C1B C13B . . 110.6(3) ?
C12B C1B C13B . . 106.6(3) ?
C2B C1B H1AA . . 109.9 ?
C12B C1B H1AA . . 109.9 ?
C13B C1B H1AA . . 109.9 ?
C3B C2B C7B . . 118.2(3) ?
C3B C2B C1B . . 120.9(3) ?
C7B C2B C1B . . 120.9(3) ?
C4B C3B C2B . . 120.7(4) ?
C4B C3B H3AA . . 119.7 ?
C2B C3B H3AA . . 119.7 ?
C3B C4B C5B . . 121.5(3) ?
C3B C4B Br1B . . 119.5(3) ?
C5B C4B Br1B . . 119.0(3) ?
C6B C5B C4B . . 117.8(3) ?
C6B C5B H5AA . . 121.1 ?
C4B C5B H5AA . . 121.1 ?
C5B C6B C7B . . 121.2(4) ?
C5B C6B H6AA . . 119.4 ?
C7B C6B H6AA . . 119.4 ?
O8B C7B C6B . . 117.0(3) ?
O8B C7B C2B . . 122.4(3) ?
C6B C7B C2B . . 120.6(3) ?
C7B O8B C9B . . 116.0(3) ?
O8B C9B N10B . . 110.1(3) ?
O8B C9B C16B . . 104.4(3) ?
N10B C9B C16B . . 108.0(3) ?
O8B C9B C13B . . 110.8(3) ?
N10B C9B C13B . . 107.2(3) ?
C16B C9B C13B . . 116.2(3) ?
C11B N10B C9B . . 129.0(3) ?
C11B N10B H10B . . 115.5 ?
C9B N10B H10B . . 115.5 ?
N10B C11B C12B . . 117.2(3) ?
N10B C11B S1B . . 121.3(3) ?
C12B C11B S1B . . 121.5(3) ?
C11B C12B C1B . . 112.9(3) ?
C11B C12B H12C . . 109.0 ?
C1B C12B H12C . . 109.0 ?
C11B C12B H12D . . 109.0 ?
C1B C12B H12D . . 109.0 ?
H12C C12B H12D . . 107.8 ?
C9B C13B C1B . . 107.0(3) ?
C9B C13B C14B . . 112.9(3) ?
C1B C13B C14B . . 113.2(3) ?
C9B C13B H13B . . 107.9 ?
C1B C13B H13B . . 107.9 ?
C14B C13B H13B . . 107.9 ?
O14B C14B C15B . . 121.6(4) ?
O14B C14B C13B . . 120.4(3) ?
C15B C14B C13B . . 118.0(3) ?
C14B C15B H15D . . 109.5 ?
C14B C15B H15F . . 109.5 ?
H15D C15B H15F . . 109.5 ?
C14B C15B H15G . . 109.5 ?
H15D C15B H15G . . 109.5 ?
H15F C15B H15G . . 109.5 ?
C9B C16B H16F . . 109.5 ?
C9B C16B H16G . . 109.5 ?
H16F C16B H16G . . 109.5 ?
C9B C16B H16D . . 109.5 ?
H16F C16B H16D . . 109.5 ?
H16G C16B H16D . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C4A . 1.918(4) ?
S1A C11A . 1.663(4) ?
C1A C2A . 1.497(5) ?
C1A C12A . 1.514(5) ?
C1A C13A . 1.556(5) ?
C1A H1A . 0.9800 ?
C2A C7A . 1.390(5) ?
C2A C3A . 1.394(5) ?
C3A C4A . 1.357(5) ?
C3A H3A . 0.9300 ?
C4A C5A . 1.374(6) ?
C5A C6A . 1.390(6) ?
C5A H5A . 0.9300 ?
C6A C7A . 1.380(5) ?
C6A H6A . 0.9300 ?
C7A O8A . 1.400(4) ?
O8A C9A . 1.431(4) ?
C9A N10A . 1.474(4) ?
C9A C16A . 1.509(5) ?
C9A C13A . 1.532(5) ?
N10A C11A . 1.342(5) ?
N10A H10A . 0.8600 ?
C11A C12A . 1.507(5) ?
C12A H12A . 0.9700 ?
C12A H12B . 0.9700 ?
C13A C14A . 1.521(5) ?
C13A H13A . 0.9800 ?
C14A O14A . 1.186(4) ?
C14A C15A . 1.501(6) ?
C15A H15A . 0.9600 ?
C15A H15B . 0.9600 ?
C15A H15C . 0.9600 ?
C16A H16A . 0.9600 ?
C16A H16B . 0.9600 ?
C16A H16C . 0.9600 ?
Br1B C4B . 1.909(4) ?
S1B C11B . 1.662(4) ?
C1B C2B . 1.509(5) ?
C1B C12B . 1.525(5) ?
C1B C13B . 1.528(5) ?
C1B H1AA . 0.9800 ?
C2B C3B . 1.381(5) ?
C2B C7B . 1.388(5) ?
C3B C4B . 1.377(5) ?
C3B H3AA . 0.9300 ?
C4B C5B . 1.387(6) ?
C5B C6B . 1.373(5) ?
C5B H5AA . 0.9300 ?
C6B C7B . 1.387(5) ?
C6B H6AA . 0.9300 ?
C7B O8B . 1.368(4) ?
O8B C9B . 1.423(4) ?
C9B N10B . 1.468(5) ?
C9B C16B . 1.518(5) ?
C9B C13B . 1.526(5) ?
N10B C11B . 1.332(5) ?
N10B H10B . 0.8600 ?
C11B C12B . 1.510(5) ?
C12B H12C . 0.9700 ?
C12B H12D . 0.9700 ?
C13B C14B . 1.549(5) ?
C13B H13B . 0.9800 ?
C14B O14B . 1.190(4) ?
C14B C15B . 1.467(6) ?
C15B H15D . 0.9600 ?
C15B H15F . 0.9600 ?
C15B H15G . 0.9600 ?
C16B H16F . 0.9600 ?
C16B H16G . 0.9600 ?
C16B H16D . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N10A H10A O14B 1_545 0.86 2.20 2.981(4) 150.1 yes
N10B H10B O14A 1_455 0.86 2.15 2.960(4) 157.2 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12A C1A C2A C7A . . . . -98.7(4) ?
C13A C1A C2A C7A . . . . 19.4(4) ?
C12A C1A C2A C3A . . . . 78.7(4) ?
C13A C1A C2A C3A . . . . -163.2(3) ?
C7A C2A C3A C4A . . . . -1.6(5) ?
C1A C2A C3A C4A . . . . -179.1(3) ?
C2A C3A C4A C5A . . . . 0.4(6) ?
C2A C3A C4A Br1A . . . . 177.7(3) ?
C3A C4A C5A C6A . . . . -0.3(6) ?
Br1A C4A C5A C6A . . . . -177.6(3) ?
C4A C5A C6A C7A . . . . 1.4(6) ?
C5A C6A C7A C2A . . . . -2.7(6) ?
C5A C6A C7A O8A . . . . 179.5(3) ?
C3A C2A C7A C6A . . . . 2.7(5) ?
C1A C2A C7A C6A . . . . -179.7(3) ?
C3A C2A C7A O8A . . . . -179.6(3) ?
C1A C2A C7A O8A . . . . -2.1(5) ?
C6A C7A O8A C9A . . . . -164.1(3) ?
C2A C7A O8A C9A . . . . 18.1(4) ?
C7A O8A C9A N10A . . . . 67.6(3) ?
C7A O8A C9A C16A . . . . -177.2(3) ?
C7A O8A C9A C13A . . . . -50.9(4) ?
O8A C9A N10A C11A . . . . -98.4(4) ?
C16A C9A N10A C11A . . . . 148.2(3) ?
C13A C9A N10A C11A . . . . 21.1(4) ?
C9A N10A C11A C12A . . . . -4.2(5) ?
C9A N10A C11A S1A . . . . 175.8(3) ?
N10A C11A C12A C1A . . . . 21.9(4) ?
S1A C11A C12A C1A . . . . -158.0(3) ?
C2A C1A C12A C11A . . . . 66.0(4) ?
C13A C1A C12A C11A . . . . -55.4(4) ?
O8A C9A C13A C14A . . . . -58.5(4) ?
N10A C9A C13A C14A . . . . -176.6(3) ?
C16A C9A C13A C14A . . . . 61.2(4) ?
O8A C9A C13A C1A . . . . 65.2(3) ?
N10A C9A C13A C1A . . . . -52.9(3) ?
C16A C9A C13A C1A . . . . -175.1(3) ?
C2A C1A C13A C14A . . . . 76.9(3) ?
C12A C1A C13A C14A . . . . -162.5(3) ?
C2A C1A C13A C9A . . . . -48.5(4) ?
C12A C1A C13A C9A . . . . 72.2(3) ?
C9A C13A C14A O14A . . . . 92.4(4) ?
C1A C13A C14A O14A . . . . -28.0(5) ?
C9A C13A C14A C15A . . . . -89.3(4) ?
C1A C13A C14A C15A . . . . 150.3(3) ?
C12B C1B C2B C3B . . . . -79.3(4) ?
C13B C1B C2B C3B . . . . 163.4(3) ?
C12B C1B C2B C7B . . . . 98.9(4) ?
C13B C1B C2B C7B . . . . -18.5(4) ?
C7B C2B C3B C4B . . . . 1.5(5) ?
C1B C2B C3B C4B . . . . 179.7(3) ?
C2B C3B C4B C5B . . . . -0.1(5) ?
C2B C3B C4B Br1B . . . . -176.8(3) ?
C3B C4B C5B C6B . . . . -0.2(5) ?
Br1B C4B C5B C6B . . . . 176.5(3) ?
C4B C5B C6B C7B . . . . -0.9(5) ?
C5B C6B C7B O8B . . . . -179.2(3) ?
C5B C6B C7B C2B . . . . 2.3(5) ?
C3B C2B C7B O8B . . . . 179.1(3) ?
C1B C2B C7B O8B . . . . 0.9(5) ?
C3B C2B C7B C6B . . . . -2.5(5) ?
C1B C2B C7B C6B . . . . 179.3(3) ?
C6B C7B O8B C9B . . . . 164.9(3) ?
C2B C7B O8B C9B . . . . -16.6(4) ?
C7B O8B C9B N10B . . . . -69.1(3) ?
C7B O8B C9B C16B . . . . 175.2(3) ?
C7B O8B C9B C13B . . . . 49.4(4) ?
O8B C9B N10B C11B . . . . 99.0(4) ?
C16B C9B N10B C11B . . . . -147.6(3) ?
C13B C9B N10B C11B . . . . -21.6(4) ?
C9B N10B C11B C12B . . . . 1.5(5) ?
C9B N10B C11B S1B . . . . -179.0(3) ?
N10B C11B C12B C1B . . . . -16.3(4) ?
S1B C11B C12B C1B . . . . 164.1(2) ?
C2B C1B C12B C11B . . . . -69.2(4) ?
C13B C1B C12B C11B . . . . 50.6(4) ?
O8B C9B C13B C1B . . . . -65.1(4) ?
N10B C9B C13B C1B . . . . 55.1(3) ?
C16B C9B C13B C1B . . . . 176.0(3) ?
O8B C9B C13B C14B . . . . 60.1(4) ?
N10B C9B C13B C14B . . . . -179.8(3) ?
C16B C9B C13B C14B . . . . -58.9(4) ?
C2B C1B C13B C9B . . . . 47.7(4) ?
C12B C1B C13B C9B . . . . -71.6(3) ?
C2B C1B C13B C14B . . . . -77.2(4) ?
C12B C1B C13B C14B . . . . 163.4(3) ?
C9B C13B C14B O14B . . . . -89.8(4) ?
C1B C13B C14B O14B . . . . 31.9(5) ?
C9B C13B C14B C15B . . . . 91.9(4) ?
C1B C13B C14B C15B . . . . -146.4(4) ?
