#------------------------------------------------------------------------------
#$Date: 2021-02-05 00:55:44 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261589 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/15/7241592.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_7241592
loop_
_publ_author_name
'Craddock, Drew E.'
'Parks, McKenzie J.'
'Taylor, Lauren A.'
'Wagner, Benjamin L.'
'Ruf, Michael'
'Wheeler, Kraig A.'
_publ_section_title
;
 Increasing the structural boundary of quasiracemate formation:
 4-substituted naphthylamides
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              210
_journal_page_last               215
_journal_paper_doi               10.1039/D0CE01331E
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C19 H16 Br N O'
_chemical_formula_sum            'C19 H16 Br N O'
_chemical_formula_weight         354.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-10-19 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                104.665(2)
_cell_angle_beta                 94.546(2)
_cell_angle_gamma                106.011(2)
_cell_formula_units_Z            4
_cell_length_a                   9.8905(5)
_cell_length_b                   10.1651(4)
_cell_length_c                   16.7066(7)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.33
_cell_volume                     1541.69(12)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51087
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.049
_diffrn_reflns_theta_min         2.170
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_exptl_absorpt_coefficient_mu    2.667
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   0.7453
_exptl_transmission_factor_min   0.6996
_refine_diff_density_max         1.782
_refine_diff_density_min         -0.785
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6090
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0379
_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)+(0.0440P)²+2.4786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0986
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4920
_reflns_number_total             6090
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01331e2.cif
_cod_data_source_block           mo_20kaw51b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7241590--7241596.cif.
;
_cod_database_code               7241592
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Br1A Br 0.88091(4) 0.88736(4) 0.03869(2) 0.03329(11) Uani 1 1 d . . . . .
O1A O 0.3178(2) 0.5534(2) 0.20324(14) 0.0227(5) Uani 1 1 d . . . . .
N1A N 0.2588(3) 0.7542(3) 0.20748(16) 0.0184(5) Uani 1 1 d . . . . .
H1A H 0.277(4) 0.822(4) 0.199(2) 0.022 Uiso 1 1 d . U . . .
C1A C 0.3435(3) 0.6718(3) 0.19037(17) 0.0182(6) Uani 1 1 d . . . . .
C2A C 0.4736(3) 0.7291(3) 0.15447(18) 0.0175(6) Uani 1 1 d . . . . .
C3A C 0.5310(3) 0.6320(3) 0.10526(19) 0.0219(6) Uani 1 1 d . . . . .
H3A H 0.485853 0.532429 0.094587 0.026 Uiso 1 1 calc R U . . .
C4A C 0.6527(4) 0.6788(3) 0.0717(2) 0.0248(7) Uani 1 1 d . . . . .
H4A H 0.690897 0.612042 0.037927 0.030 Uiso 1 1 calc R U . . .
C5A C 0.7179(3) 0.8239(3) 0.08812(19) 0.0221(6) Uani 1 1 d . . . . .
C6A C 0.6658(3) 0.9224(3) 0.13826(19) 0.0221(6) Uani 1 1 d . . . . .
H6A H 0.713648 1.021708 0.150226 0.027 Uiso 1 1 calc R U . . .
C7A C 0.5433(3) 0.8754(3) 0.17105(18) 0.0207(6) Uani 1 1 d . . . . .
H7A H 0.506182 0.942915 0.205024 0.025 Uiso 1 1 calc R U . . .
C8A C 0.1368(3) 0.7152(3) 0.25062(18) 0.0182(6) Uani 1 1 d . . . . .
H8A H 0.091348 0.609394 0.229594 0.022 Uiso 1 1 calc R U . . .
C9A C 0.0284(3) 0.7871(3) 0.22814(19) 0.0215(6) Uani 1 1 d . . . . .
H9A1 H 0.070082 0.891101 0.250017 0.032 Uiso 1 1 calc R U . . .
H9A2 H -0.057043 0.755951 0.252918 0.032 Uiso 1 1 calc R U . . .
H9A3 H 0.002648 0.760527 0.167060 0.032 Uiso 1 1 calc R U . . .
C10A C 0.1868(3) 0.7550(3) 0.34444(18) 0.0162(6) Uani 1 1 d . . . . .
C11A C 0.1593(3) 0.6555(3) 0.38768(18) 0.0167(6) Uani 1 1 d . . . . .
H11A H 0.104037 0.559976 0.358743 0.020 Uiso 1 1 calc R U . . .
C12A C 0.2110(3) 0.6906(3) 0.47434(18) 0.0152(6) Uani 1 1 d . . . . .
C13A C 0.1853(3) 0.5877(3) 0.51931(19) 0.0180(6) Uani 1 1 d . . . . .
H13A H 0.130856 0.491559 0.491272 0.022 Uiso 1 1 calc R U . . .
C14A C 0.2383(3) 0.6257(3) 0.60281(19) 0.0211(6) Uani 1 1 d . . . . .
H14A H 0.220478 0.555784 0.632344 0.025 Uiso 1 1 calc R U . . .
C15A C 0.3195(3) 0.7687(3) 0.64560(19) 0.0210(6) Uani 1 1 d . . . . .
H15A H 0.355591 0.794024 0.703667 0.025 Uiso 1 1 calc R U . . .
C16A C 0.3464(3) 0.8703(3) 0.60382(19) 0.0193(6) Uani 1 1 d . . . . .
H16A H 0.400942 0.965851 0.633051 0.023 Uiso 1 1 calc R U . . .
C17A C 0.2936(3) 0.8342(3) 0.51750(18) 0.0154(6) Uani 1 1 d . . . . .
C18A C 0.3192(3) 0.9366(3) 0.47165(19) 0.0175(6) Uani 1 1 d . . . . .
H18A H 0.373011 1.032946 0.499614 0.021 Uiso 1 1 calc R U . . .
C19A C 0.2676(3) 0.8984(3) 0.38797(19) 0.0184(6) Uani 1 1 d . . . . .
H19A H 0.285857 0.968566 0.358569 0.022 Uiso 1 1 calc R U . . .
Br1B Br 0.89222(4) 0.42390(4) 0.05663(2) 0.03076(10) Uani 1 1 d . . . . .
O1B O 0.3003(2) 0.0391(2) 0.17464(15) 0.0266(5) Uani 1 1 d . . . . .
N1B N 0.2601(3) 0.2537(3) 0.21138(16) 0.0183(5) Uani 1 1 d . . . . .
H1B H 0.283(4) 0.327(4) 0.208(2) 0.022 Uiso 1 1 d . U . . .
C1B C 0.3359(3) 0.1680(3) 0.17992(18) 0.0184(6) Uani 1 1 d . . . . .
C2B C 0.4699(3) 0.2362(3) 0.15067(18) 0.0169(6) Uani 1 1 d . . . . .
C3B C 0.5004(4) 0.1639(3) 0.07516(19) 0.0230(6) Uani 1 1 d . . . . .
H3B H 0.435126 0.074894 0.042804 0.028 Uiso 1 1 calc R U . . .
C4B C 0.6250(4) 0.2204(3) 0.04677(19) 0.0239(7) Uani 1 1 d . . . . .
H4B H 0.644289 0.172407 -0.005641 0.029 Uiso 1 1 calc R U . . .
C5B C 0.7212(3) 0.3480(3) 0.09591(19) 0.0207(6) Uani 1 1 d . . . . .
C6B C 0.6945(3) 0.4207(3) 0.17148(19) 0.0220(6) Uani 1 1 d . . . . .
H6B H 0.762564 0.507130 0.204898 0.026 Uiso 1 1 calc R U . . .
C7B C 0.5667(3) 0.3660(3) 0.19825(19) 0.0210(6) Uani 1 1 d . . . . .
H7B H 0.545391 0.417243 0.249101 0.025 Uiso 1 1 calc R U . . .
C8B C 0.1282(3) 0.1997(3) 0.24239(19) 0.0192(6) Uani 1 1 d . . . . .
H8B H 0.087371 0.095645 0.211930 0.023 Uiso 1 1 calc R U . . .
C9B C 0.0215(3) 0.2736(3) 0.2191(2) 0.0225(6) Uani 1 1 d . . . . .
H9B1 H 0.065576 0.377419 0.239231 0.034 Uiso 1 1 calc R U . . .
H9B2 H -0.063285 0.246246 0.245137 0.034 Uiso 1 1 calc R U . . .
H9B3 H -0.005946 0.244319 0.158055 0.034 Uiso 1 1 calc R U . . .
C10B C 0.1532(3) 0.2130(3) 0.33578(18) 0.0174(6) Uani 1 1 d . . . . .
C11B C 0.2837(3) 0.2745(3) 0.38562(18) 0.0167(6) Uani 1 1 d . . . . .
H11B H 0.363760 0.315456 0.362228 0.020 Uiso 1 1 calc R U . . .
C12B C 0.3024(3) 0.2785(3) 0.47128(18) 0.0154(6) Uani 1 1 d . . . . .
C13B C 0.4381(3) 0.3370(3) 0.52284(19) 0.0186(6) Uani 1 1 d . . . . .
H13B H 0.519389 0.377037 0.500112 0.022 Uiso 1 1 calc R U . . .
C14B C 0.4534(3) 0.3366(3) 0.60529(19) 0.0215(6) Uani 1 1 d . . . . .
H14B H 0.544944 0.375912 0.639021 0.026 Uiso 1 1 calc R U . . .
C15B C 0.3338(3) 0.2780(3) 0.63980(19) 0.0210(6) Uani 1 1 d . . . . .
H15B H 0.345071 0.278573 0.696899 0.025 Uiso 1 1 calc R U . . .
C16B C 0.2012(3) 0.2202(3) 0.59178(19) 0.0205(6) Uani 1 1 d . . . . .
H16B H 0.121353 0.181094 0.615881 0.025 Uiso 1 1 calc R U . . .
C17B C 0.1823(3) 0.2181(3) 0.50618(18) 0.0162(6) Uani 1 1 d . . . . .
C18B C 0.0479(3) 0.1561(3) 0.45420(19) 0.0186(6) Uani 1 1 d . . . . .
H18B H -0.033428 0.116237 0.477004 0.022 Uiso 1 1 calc R U . . .
C19B C 0.0332(3) 0.1525(3) 0.37168(19) 0.0189(6) Uani 1 1 d . . . . .
H19B H -0.057997 0.109325 0.337673 0.023 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 0.0033 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C8A 121.5(2) . . ?
C1A N1A H1A 119(3) . . ?
C8A N1A H1A 119(3) . . ?
O1A C1A N1A 122.6(3) . . ?
O1A C1A C2A 120.4(3) . . ?
N1A C1A C2A 117.0(2) . . ?
C3A C2A C7A 118.7(3) . . ?
C3A C2A C1A 118.3(3) . . ?
C7A C2A C1A 122.9(3) . . ?
C4A C3A C2A 120.9(3) . . ?
C4A C3A H3A 119.5 . . ?
C2A C3A H3A 119.5 . . ?
C5A C4A C3A 119.0(3) . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A H4A 120.5 . . ?
C6A C5A C4A 121.4(3) . . ?
C6A C5A Br1A 119.7(2) . . ?
C4A C5A Br1A 118.9(2) . . ?
C5A C6A C7A 119.4(3) . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A H6A 120.3 . . ?
C6A C7A C2A 120.4(3) . . ?
C6A C7A H7A 119.8 . . ?
C2A C7A H7A 119.8 . . ?
N1A C8A C10A 110.1(2) . . ?
N1A C8A C9A 108.6(2) . . ?
C10A C8A C9A 113.0(2) . . ?
N1A C8A H8A 108.3 . . ?
C10A C8A H8A 108.3 . . ?
C9A C8A H8A 108.3 . . ?
C8A C9A H9A1 109.5 . . ?
C8A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C8A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C11A C10A C19A 119.1(3) . . ?
C11A C10A C8A 121.6(2) . . ?
C19A C10A C8A 119.2(2) . . ?
C10A C11A C12A 121.9(3) . . ?
C10A C11A H11A 119.1 . . ?
C12A C11A H11A 119.1 . . ?
C13A C12A C11A 122.3(3) . . ?
C13A C12A C17A 118.9(3) . . ?
C11A C12A C17A 118.8(2) . . ?
C14A C13A C12A 120.5(3) . . ?
C14A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C13A C14A C15A 120.5(3) . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A H14A 119.8 . . ?
C16A C15A C14A 120.4(3) . . ?
C16A C15A H15A 119.8 . . ?
C14A C15A H15A 119.8 . . ?
C15A C16A C17A 120.5(3) . . ?
C15A C16A H16A 119.8 . . ?
C17A C16A H16A 119.8 . . ?
C16A C17A C18A 122.3(3) . . ?
C16A C17A C12A 119.3(2) . . ?
C18A C17A C12A 118.4(3) . . ?
C19A C18A C17A 121.0(3) . . ?
C19A C18A H18A 119.5 . . ?
C17A C18A H18A 119.5 . . ?
C18A C19A C10A 120.8(3) . . ?
C18A C19A H19A 119.6 . . ?
C10A C19A H19A 119.6 . . ?
C1B N1B C8B 121.4(2) . . ?
C1B N1B H1B 117(3) . . ?
C8B N1B H1B 121(3) . . ?
O1B C1B N1B 123.2(3) . . ?
O1B C1B C2B 120.3(3) . . ?
N1B C1B C2B 116.4(2) . . ?
C3B C2B C7B 119.4(3) . . ?
C3B C2B C1B 118.5(3) . . ?
C7B C2B C1B 122.1(3) . . ?
C4B C3B C2B 120.6(3) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C5B 119.0(3) . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B H4B 120.5 . . ?
C6B C5B C4B 121.6(3) . . ?
C6B C5B Br1B 119.8(2) . . ?
C4B C5B Br1B 118.6(2) . . ?
C5B C6B C7B 119.2(3) . . ?
C5B C6B H6B 120.4 . . ?
C7B C6B H6B 120.4 . . ?
C6B C7B C2B 120.2(3) . . ?
C6B C7B H7B 119.9 . . ?
C2B C7B H7B 119.9 . . ?
N1B C8B C10B 112.4(2) . . ?
N1B C8B C9B 108.9(2) . . ?
C10B C8B C9B 113.2(2) . . ?
N1B C8B H8B 107.3 . . ?
C10B C8B H8B 107.3 . . ?
C9B C8B H8B 107.3 . . ?
C8B C9B H9B1 109.5 . . ?
C8B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C8B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C11B C10B C19B 118.8(3) . . ?
C11B C10B C8B 123.8(3) . . ?
C19B C10B C8B 117.4(3) . . ?
C10B C11B C12B 121.6(3) . . ?
C10B C11B H11B 119.2 . . ?
C12B C11B H11B 119.2 . . ?
C11B C12B C13B 122.2(3) . . ?
C11B C12B C17B 119.0(3) . . ?
C13B C12B C17B 118.8(3) . . ?
C14B C13B C12B 120.9(3) . . ?
C14B C13B H13B 119.6 . . ?
C12B C13B H13B 119.6 . . ?
C13B C14B C15B 120.1(3) . . ?
C13B C14B H14B 119.9 . . ?
C15B C14B H14B 119.9 . . ?
C16B C15B C14B 120.6(3) . . ?
C16B C15B H15B 119.7 . . ?
C14B C15B H15B 119.7 . . ?
C15B C16B C17B 120.5(3) . . ?
C15B C16B H16B 119.7 . . ?
C17B C16B H16B 119.7 . . ?
C18B C17B C12B 118.8(3) . . ?
C18B C17B C16B 122.1(3) . . ?
C12B C17B C16B 119.1(3) . . ?
C19B C18B C17B 120.9(3) . . ?
C19B C18B H18B 119.5 . . ?
C17B C18B H18B 119.5 . . ?
C18B C19B C10B 120.8(3) . . ?
C18B C19B H19B 119.6 . . ?
C10B C19B H19B 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
Br1A C5A 1.899(3) . ?
O1A C1A 1.238(3) . ?
N1A C1A 1.337(4) . ?
N1A C8A 1.466(4) . ?
N1A H1A 0.72(4) . ?
C1A C2A 1.497(4) . ?
C2A C3A 1.394(4) . ?
C2A C7A 1.400(4) . ?
C3A C4A 1.384(4) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(4) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.378(4) . ?
C6A C7A 1.384(4) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C8A C10A 1.520(4) . ?
C8A C9A 1.527(4) . ?
C8A H8A 1.0000 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C10A C11A 1.367(4) . ?
C10A C19A 1.422(4) . ?
C11A C12A 1.416(4) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.415(4) . ?
C12A C17A 1.426(4) . ?
C13A C14A 1.367(4) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.417(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.367(4) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.412(4) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.422(4) . ?
C18A C19A 1.367(4) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?
Br1B C5B 1.898(3) . ?
O1B C1B 1.237(3) . ?
N1B C1B 1.337(4) . ?
N1B C8B 1.458(4) . ?
N1B H1B 0.73(4) . ?
C1B C2B 1.498(4) . ?
C2B C3B 1.392(4) . ?
C2B C7B 1.393(4) . ?
C3B C4B 1.383(4) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.385(4) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.378(4) . ?
C6B C7B 1.391(4) . ?
C6B H6B 0.9500 . ?
C7B H7B 0.9500 . ?
C8B C10B 1.526(4) . ?
C8B C9B 1.533(4) . ?
C8B H8B 1.0000 . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C10B C11B 1.368(4) . ?
C10B C19B 1.430(4) . ?
C11B C12B 1.417(4) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.419(4) . ?
C12B C17B 1.420(4) . ?
C13B C14B 1.375(4) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.407(4) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.370(4) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.422(4) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.413(4) . ?
C18B C19B 1.365(4) . ?
C18B H18B 0.9500 . ?
C19B H19B 0.9500 . ?
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
N1A H1A O1B 0.72(4) 2.29(4) 3.007(3) 171(4) 1_565 yes
N1B H1B O1A 0.73(4) 2.25(4) 2.981(3) 170(4) . 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
C8A N1A C1A O1A 6.2(4) . . . . ?
C8A N1A C1A C2A -173.7(2) . . . . ?
O1A C1A C2A C3A 26.0(4) . . . . ?
N1A C1A C2A C3A -154.1(3) . . . . ?
O1A C1A C2A C7A -151.3(3) . . . . ?
N1A C1A C2A C7A 28.6(4) . . . . ?
C7A C2A C3A C4A -1.4(4) . . . . ?
C1A C2A C3A C4A -178.8(3) . . . . ?
C2A C3A C4A C5A 0.4(5) . . . . ?
C3A C4A C5A C6A 1.2(5) . . . . ?
C3A C4A C5A Br1A -177.8(2) . . . . ?
C4A C5A C6A C7A -1.9(5) . . . . ?
Br1A C5A C6A C7A 177.1(2) . . . . ?
C5A C6A C7A C2A 0.9(4) . . . . ?
C3A C2A C7A C6A 0.7(4) . . . . ?
C1A C2A C7A C6A 178.0(3) . . . . ?
C1A N1A C8A C10A 80.0(3) . . . . ?
C1A N1A C8A C9A -155.8(3) . . . . ?
N1A C8A C10A C11A -122.6(3) . . . . ?
C9A C8A C10A C11A 115.8(3) . . . . ?
N1A C8A C10A C19A 55.6(3) . . . . ?
C9A C8A C10A C19A -66.0(3) . . . . ?
C19A C10A C11A C12A -1.0(4) . . . . ?
C8A C10A C11A C12A 177.2(3) . . . . ?
C10A C11A C12A C13A -178.8(3) . . . . ?
C10A C11A C12A C17A 0.2(4) . . . . ?
C11A C12A C13A C14A 179.3(3) . . . . ?
C17A C12A C13A C14A 0.3(4) . . . . ?
C12A C13A C14A C15A 0.1(4) . . . . ?
C13A C14A C15A C16A -0.2(5) . . . . ?
C14A C15A C16A C17A 0.0(4) . . . . ?
C15A C16A C17A C18A -179.9(3) . . . . ?
C15A C16A C17A C12A 0.4(4) . . . . ?
C13A C12A C17A C16A -0.6(4) . . . . ?
C11A C12A C17A C16A -179.6(3) . . . . ?
C13A C12A C17A C18A 179.8(3) . . . . ?
C11A C12A C17A C18A 0.7(4) . . . . ?
C16A C17A C18A C19A 179.6(3) . . . . ?
C12A C17A C18A C19A -0.8(4) . . . . ?
C17A C18A C19A C10A -0.1(4) . . . . ?
C11A C10A C19A C18A 1.0(4) . . . . ?
C8A C10A C19A C18A -177.3(3) . . . . ?
C8B N1B C1B O1B 0.2(5) . . . . ?
C8B N1B C1B C2B -179.6(2) . . . . ?
O1B C1B C2B C3B 43.2(4) . . . . ?
N1B C1B C2B C3B -137.0(3) . . . . ?
O1B C1B C2B C7B -134.1(3) . . . . ?
N1B C1B C2B C7B 45.7(4) . . . . ?
C7B C2B C3B C4B -0.6(4) . . . . ?
C1B C2B C3B C4B -178.0(3) . . . . ?
C2B C3B C4B C5B 2.0(5) . . . . ?
C3B C4B C5B C6B -1.1(5) . . . . ?
C3B C4B C5B Br1B 179.6(2) . . . . ?
C4B C5B C6B C7B -1.3(4) . . . . ?
Br1B C5B C6B C7B 178.0(2) . . . . ?
C5B C6B C7B C2B 2.7(4) . . . . ?
C3B C2B C7B C6B -1.7(4) . . . . ?
C1B C2B C7B C6B 175.5(3) . . . . ?
C1B N1B C8B C10B 91.3(3) . . . . ?
C1B N1B C8B C9B -142.4(3) . . . . ?
N1B C8B C10B C11B 2.7(4) . . . . ?
C9B C8B C10B C11B -121.2(3) . . . . ?
N1B C8B C10B C19B -174.9(2) . . . . ?
C9B C8B C10B C19B 61.2(3) . . . . ?
C19B C10B C11B C12B 0.5(4) . . . . ?
C8B C10B C11B C12B -177.1(2) . . . . ?
C10B C11B C12B C13B 177.6(3) . . . . ?
C10B C11B C12B C17B -0.5(4) . . . . ?
C11B C12B C13B C14B -178.6(3) . . . . ?
C17B C12B C13B C14B -0.5(4) . . . . ?
C12B C13B C14B C15B -0.2(4) . . . . ?
C13B C14B C15B C16B 0.4(4) . . . . ?
C14B C15B C16B C17B 0.1(4) . . . . ?
C11B C12B C17B C18B 0.0(4) . . . . ?
C13B C12B C17B C18B -178.2(2) . . . . ?
C11B C12B C17B C16B 179.1(2) . . . . ?
C13B C12B C17B C16B 0.9(4) . . . . ?
C15B C16B C17B C18B 178.3(3) . . . . ?
C15B C16B C17B C12B -0.8(4) . . . . ?
C12B C17B C18B C19B 0.6(4) . . . . ?
C16B C17B C18B C19B -178.4(3) . . . . ?
C17B C18B C19B C10B -0.7(4) . . . . ?
C11B C10B C19B C18B 0.2(4) . . . . ?
C8B C10B C19B C18B 177.9(3) . . . . ?
