#------------------------------------------------------------------------------
#$Date: 2020-10-23 07:36:19 +0300 (Fri, 23 Oct 2020) $
#$Revision: 258573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022268.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_2022268
loop_
_publ_author_name
'Okezue, Mercy'
'Smith, Daniel'
'Zeller, Matthias'
'Byrn, Stephen R.'
'Smith, Pamela'
'Bogandowich-Knipp, Susan'
'Purcell, Dale K.'
'Clase, Kari L.'
_publ_section_title
;
 Crystal structures of salts of bedaquiline
;
_journal_coeditor_code           OV3143
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620013455
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C32 H32 Br N2 O2 +, C7 H5 O2 -, 1.166H2 O'
_chemical_formula_moiety         'C32 H32 Br N2 O2 +, C7 H5 O2 -, 1.166(H2 O)'
_chemical_formula_sum            'C39 H39.34 Br N2 O5.17'
_chemical_formula_weight         698.70
_chemical_name_common
;
Bedaqulinium benzoate 1.166-hydrate
;
_chemical_name_systematic
'[4-(6-Bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium benzoate hydrate'
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 99.8450(17)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.6384(5)
_cell_length_b                   7.9259(3)
_cell_length_c                   17.5249(8)
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.9868
_cell_measurement_theta_min      2.3592
_cell_volume                     1729.63(12)
_computing_cell_refinement
;
SAINT (Bruker, 2019)
;
_computing_data_collection
;
APEX3 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT (Bruker, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and
shelXle (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker D8 Quest diffractometer with PhotonII charge-integrating pixel
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            80228
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.168
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.235
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2016; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_description       rod
_exptl_crystal_F_000             727
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.484
_refine_ls_abs_structure_details
;
Flack x determined using 4051 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         13080
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0318
_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)+(0.0275P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0725
_reflns_number_gt                10456
_reflns_number_total             13080
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3143sup1.cif
_cod_data_source_block           4a
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022268
_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_min   0.550
_shelx_estimated_absorpt_t_max   0.856
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 1.08589(2) 0.23491(3) -0.10932(2) 0.03179(6) Uani d 1 . .
O O1 0.75158(11) 0.32496(17) 0.21175(8) 0.0226(3) Uani d 1 . .
H H1B 0.726(2) 0.2891(12) 0.1673(15) 0.034 Uiso calc 1 . .
O O2 1.09216(11) 0.03313(19) 0.34490(8) 0.0250(3) Uani d 1 . .
O O3 0.45306(14) 0.2726(2) 0.05187(10) 0.0416(4) Uani d 1 . .
O O4 0.33269(13) 0.4451(2) -0.01531(8) 0.0313(3) Uani d 1 . .
O O5 0.67059(14) 0.2732(2) 0.06194(9) 0.0333(4) Uani d 1 . .
H H5D 0.678(3) 0.173(5) 0.0399(18) 0.050 Uiso d 1 . .
H H5E 0.609(3) 0.282(4) 0.0580(18) 0.050 Uiso d 1 . .
O O6 1.3652(11) -0.1662(18) 0.2755(8) 0.061(5) Uani d 0.166(7) . .
H H6D 1.381796 -0.060138 0.281851 0.091 Uiso d 0.166(7) . .
H H6E 1.295716 -0.160377 0.260652 0.091 Uiso d 0.166(7) . .
N N1 0.59081(12) -0.1394(2) 0.14129(9) 0.0209(3) Uani d 1 . .
H H1 0.621515 -0.107941 0.094301 0.025 Uiso calc 1 . .
N N2 1.14361(13) 0.0185(2) 0.22591(10) 0.0245(3) Uani d 1 . .
C C1 0.89931(14) 0.1917(2) 0.29663(10) 0.0177(3) Uani d 1 . .
H H1A 0.912833 0.105727 0.338929 0.021 Uiso calc 1 . .
C C2 0.77558(14) 0.1863(2) 0.26328(10) 0.0183(3) Uani d 1 . .
C C3 0.74525(14) 0.0197(2) 0.21876(10) 0.0189(3) Uani d 1 . .
H H3A 0.773132 0.022355 0.169312 0.023 Uiso calc 1 . .
H H3B 0.779760 -0.075971 0.249780 0.023 Uiso calc 1 . .
C C4 0.62435(14) -0.0081(3) 0.20190(10) 0.0211(3) Uani d 1 . .
H H4A 0.599796 -0.042486 0.250303 0.025 Uiso calc 1 . .
H H4B 0.588573 0.099757 0.184672 0.025 Uiso calc 1 . .
C C5 0.62902(18) -0.3115(3) 0.16528(14) 0.0318(5) Uani d 1 . .
H H5A 0.607261 -0.390295 0.122359 0.048 Uiso calc 1 . .
H H5B 0.597537 -0.346948 0.210080 0.048 Uiso calc 1 . .
H H5C 0.707487 -0.311025 0.179237 0.048 Uiso calc 1 . .
C C6 0.47158(16) -0.1387(3) 0.11978(13) 0.0306(4) Uani d 1 . .
H H6A 0.447484 -0.027521 0.099337 0.046 Uiso calc 1 . .
H H6B 0.439568 -0.163370 0.165684 0.046 Uiso calc 1 . .
H H6C 0.449243 -0.224808 0.080161 0.046 Uiso calc 1 . .
C C7 0.71486(13) 0.2170(3) 0.33194(9) 0.0202(3) Uani d 1 . .
C C8 0.66495(17) 0.3697(3) 0.33479(12) 0.0292(4) Uani d 1 . .
H H8 0.666506 0.447440 0.293730 0.035 Uiso calc 1 . .
C C9 0.6113(2) 0.4171(3) 0.39581(13) 0.0376(5) Uani d 1 . .
H H9 0.578160 0.524760 0.395368 0.045 Uiso calc 1 . .
C C10 0.6071(2) 0.3088(3) 0.45499(13) 0.0365(5) Uani d 1 . .
H H10 0.571006 0.340816 0.496032 0.044 Uiso calc 1 . .
C C11 0.65593(18) 0.1492(3) 0.45603(12) 0.0315(5) Uani d 1 . .
C C12 0.6518(2) 0.0367(4) 0.51821(15) 0.0478(7) Uani d 1 . .
H H12 0.615365 0.070222 0.558867 0.057 Uiso calc 1 . .
C C13 0.6981(3) -0.1164(4) 0.52119(18) 0.0583(8) Uani d 1 . .
H H13 0.693912 -0.189679 0.563465 0.070 Uiso calc 1 . .
C C14 0.7528(2) -0.1682(4) 0.46177(16) 0.0469(7) Uani d 1 . .
H H14 0.785004 -0.276756 0.463796 0.056 Uiso calc 1 . .
C C15 0.75993(18) -0.0622(3) 0.40071(12) 0.0304(4) Uani d 1 . .
H H15 0.798548 -0.098306 0.361670 0.036 Uiso calc 1 . .
C C16 0.71136(16) 0.0992(3) 0.39441(11) 0.0239(4) Uani d 1 . .
C C17 0.93134(14) 0.3615(2) 0.33346(10) 0.0187(3) Uani d 1 . .
C C18 0.93961(18) 0.3834(3) 0.41341(11) 0.0268(4) Uani d 1 . .
H H18 0.925381 0.291144 0.444733 0.032 Uiso calc 1 . .
C C19 0.9683(2) 0.5381(3) 0.44745(11) 0.0327(5) Uani d 1 . .
H H19 0.973412 0.551193 0.501838 0.039 Uiso calc 1 . .
C C20 0.98963(19) 0.6738(3) 0.40278(11) 0.0314(5) Uani d 1 . .
H H20 1.010481 0.779369 0.426327 0.038 Uiso calc 1 . .
C C21 0.98022(19) 0.6541(3) 0.32309(11) 0.0292(4) Uani d 1 . .
H H21 0.993225 0.747126 0.291782 0.035 Uiso calc 1 . .
C C22 0.95196(17) 0.4994(3) 0.28939(11) 0.0254(4) Uani d 1 . .
H H22 0.946527 0.487081 0.234939 0.031 Uiso calc 1 . .
C C23 0.97303(14) 0.1486(2) 0.23939(10) 0.0188(3) Uani d 1 . .
C C24 0.95734(14) 0.1960(2) 0.16317(10) 0.0199(4) Uani d 1 . .
H H24 0.894360 0.256618 0.141861 0.024 Uiso calc 1 . .
C C25 1.03406(14) 0.1555(3) 0.11563(11) 0.0209(3) Uani d 1 . .
C C26 1.02197(14) 0.2073(3) 0.03709(10) 0.0230(4) Uani d 1 . .
H H26 0.961896 0.272839 0.014304 0.028 Uiso calc 1 . .
C C27 1.09881(16) 0.1605(3) -0.00506(11) 0.0239(4) Uani d 1 . .
C C28 1.18724(16) 0.0604(3) 0.02554(12) 0.0282(4) Uani d 1 . .
H H28 1.237701 0.026726 -0.005945 0.034 Uiso calc 1 . .
C C29 1.19988(17) 0.0116(3) 0.10170(13) 0.0289(4) Uani d 1 . .
H H29 1.259621 -0.056265 0.123021 0.035 Uiso calc 1 . .
C C30 1.12503(15) 0.0612(3) 0.14873(11) 0.0226(4) Uani d 1 . .
C C31 1.07295(15) 0.0640(2) 0.26745(11) 0.0207(3) Uani d 1 . .
C C32 1.19411(18) -0.0419(3) 0.37533(14) 0.0364(5) Uani d 1 . .
H H32A 1.197179 -0.156057 0.354303 0.055 Uiso calc 1 . .
H H32B 1.202846 -0.047604 0.431923 0.055 Uiso calc 1 . .
H H32C 1.251863 0.026661 0.360523 0.055 Uiso calc 1 . .
C C33 0.37747(16) 0.3748(3) 0.04720(12) 0.0258(4) Uani d 1 . .
C C34 0.33351(16) 0.4182(3) 0.11951(11) 0.0244(4) Uani d 1 . .
C C35 0.23897(19) 0.5090(3) 0.11598(13) 0.0331(5) Uani d 1 . .
H H35 0.202051 0.548308 0.067447 0.040 Uiso calc 1 . .
C C36 0.1981(2) 0.5426(4) 0.18289(15) 0.0487(7) Uani d 1 . .
H H36 0.133006 0.603990 0.179969 0.058 Uiso calc 1 . .
C C37 0.2515(2) 0.4876(5) 0.25356(15) 0.0531(8) Uani d 1 . .
H H37 0.223153 0.510905 0.299262 0.064 Uiso calc 1 . .
C C38 0.3462(2) 0.3986(4) 0.25814(14) 0.0523(8) Uani d 1 . .
H H38 0.383205 0.360736 0.306920 0.063 Uiso calc 1 . .
C C39 0.3871(2) 0.3647(4) 0.19136(13) 0.0394(6) Uani d 1 . .
H H39 0.452599 0.304104 0.194674 0.047 Uiso calc 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'
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
C2 O1 H1B . . 109.5 ?
C31 O2 C32 . . 116.16(16) ?
H5D O5 H5E . . 103(3) ?
H6D O6 H6E . . 101.2 ?
C5 N1 C6 . . 109.94(17) ?
C5 N1 C4 . . 113.54(15) ?
C6 N1 C4 . . 109.21(16) ?
C5 N1 H1 . . 108.0 ?
C6 N1 H1 . . 108.0 ?
C4 N1 H1 . . 108.0 ?
C31 N2 C30 . . 117.76(16) ?
C17 C1 C23 . . 109.33(14) ?
C17 C1 C2 . . 110.99(14) ?
C23 C1 C2 . . 115.54(14) ?
C17 C1 H1A . . 106.8 ?
C23 C1 H1A . . 106.8 ?
C2 C1 H1A . . 106.8 ?
O1 C2 C3 . . 109.36(14) ?
O1 C2 C7 . . 106.90(15) ?
C3 C2 C7 . . 114.32(15) ?
O1 C2 C1 . . 107.77(14) ?
C3 C2 C1 . . 110.81(14) ?
C7 C2 C1 . . 107.42(13) ?
C4 C3 C2 . . 112.06(15) ?
C4 C3 H3A . . 109.2 ?
C2 C3 H3A . . 109.2 ?
C4 C3 H3B . . 109.2 ?
C2 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
N1 C4 C3 . . 113.09(15) ?
N1 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
N1 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
N1 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N1 C6 H6A . . 109.5 ?
N1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
N1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C16 . . 118.01(16) ?
C8 C7 C2 . . 117.30(17) ?
C16 C7 C2 . . 124.64(18) ?
C7 C8 C9 . . 123.1(2) ?
C7 C8 H8 . . 118.4 ?
C9 C8 H8 . . 118.4 ?
C10 C9 C8 . . 119.9(2) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C9 C10 C11 . . 120.4(2) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.2(2) ?
C10 C11 C16 . . 120.5(2) ?
C12 C11 C16 . . 119.3(2) ?
C13 C12 C11 . . 121.7(2) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C12 C13 C14 . . 120.0(2) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
C15 C14 C13 . . 120.3(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 121.9(2) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
C15 C16 C11 . . 116.81(19) ?
C15 C16 C7 . . 125.05(18) ?
C11 C16 C7 . . 118.14(19) ?
C22 C17 C18 . . 118.08(17) ?
C22 C17 C1 . . 121.56(15) ?
C18 C17 C1 . . 120.36(16) ?
C19 C18 C17 . . 120.74(18) ?
C19 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C20 C19 C18 . . 120.44(18) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C19 C20 C21 . . 119.3(2) ?
C19 C20 H20 . . 120.3 ?
C21 C20 H20 . . 120.3 ?
C22 C21 C20 . . 120.05(19) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C17 . . 121.36(17) ?
C21 C22 H22 . . 119.3 ?
C17 C22 H22 . . 119.3 ?
C24 C23 C31 . . 115.67(16) ?
C24 C23 C1 . . 125.41(16) ?
C31 C23 C1 . . 118.68(16) ?
C23 C24 C25 . . 120.77(16) ?
C23 C24 H24 . . 119.6 ?
C25 C24 H24 . . 119.6 ?
C30 C25 C24 . . 117.98(17) ?
C30 C25 C26 . . 119.80(16) ?
C24 C25 C26 . . 122.23(17) ?
C27 C26 C25 . . 118.48(18) ?
C27 C26 H26 . . 120.8 ?
C25 C26 H26 . . 120.8 ?
C26 C27 C28 . . 122.72(19) ?
C26 C27 Br1 . . 118.87(16) ?
C28 C27 Br1 . . 118.41(14) ?
C29 C28 C27 . . 118.98(18) ?
C29 C28 H28 . . 120.5 ?
C27 C28 H28 . . 120.5 ?
C28 C29 C30 . . 120.7(2) ?
C28 C29 H29 . . 119.6 ?
C30 C29 H29 . . 119.6 ?
N2 C30 C25 . . 121.68(17) ?
N2 C30 C29 . . 119.12(18) ?
C25 C30 C29 . . 119.19(18) ?
N2 C31 O2 . . 119.21(17) ?
N2 C31 C23 . . 125.87(17) ?
O2 C31 C23 . . 114.92(16) ?
O2 C32 H32A . . 109.5 ?
O2 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
O2 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
O3 C33 O4 . . 124.42(19) ?
O3 C33 C34 . . 118.83(19) ?
O4 C33 C34 . . 116.74(18) ?
C35 C34 C39 . . 118.76(19) ?
C35 C34 C33 . . 121.28(18) ?
C39 C34 C33 . . 119.95(19) ?
C36 C35 C34 . . 120.3(2) ?
C36 C35 H35 . . 119.8 ?
C34 C35 H35 . . 119.8 ?
C37 C36 C35 . . 120.3(2) ?
C37 C36 H36 . . 119.9 ?
C35 C36 H36 . . 119.9 ?
C36 C37 C38 . . 120.1(2) ?
C36 C37 H37 . . 120.0 ?
C38 C37 H37 . . 120.0 ?
C37 C38 C39 . . 119.7(2) ?
C37 C38 H38 . . 120.1 ?
C39 C38 H38 . . 120.1 ?
C38 C39 C34 . . 120.8(2) ?
C38 C39 H39 . . 119.6 ?
C34 C39 H39 . . 119.6 ?
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
Br1 C27 . 1.900(2) ?
O1 C2 . 1.422(2) ?
O1 H1B . 0.84(3) ?
O2 C31 . 1.360(2) ?
O2 C32 . 1.437(2) ?
O3 C33 . 1.244(3) ?
O4 C33 . 1.273(3) ?
O5 H5D . 0.90(4) ?
O5 H5E . 0.77(3) ?
O6 H6D . 0.8692 ?
O6 H6E . 0.8735 ?
N1 C5 . 1.484(3) ?
N1 C6 . 1.489(2) ?
N1 C4 . 1.495(2) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.296(2) ?
N2 C30 . 1.375(3) ?
C1 C17 . 1.517(2) ?
C1 C23 . 1.520(2) ?
C1 C2 . 1.574(2) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.548(3) ?
C2 C7 . 1.553(2) ?
C3 C4 . 1.522(2) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C8 . 1.369(3) ?
C7 C16 . 1.446(3) ?
C8 C9 . 1.412(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.354(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.406(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.416(3) ?
C11 C16 . 1.440(3) ?
C12 C13 . 1.345(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.406(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.375(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.414(3) ?
C15 H15 . 0.9500 ?
C17 C22 . 1.388(3) ?
C17 C18 . 1.398(3) ?
C18 C19 . 1.385(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.383(3) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.390(3) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.381(3) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.369(2) ?
C23 C31 . 1.440(3) ?
C24 C25 . 1.419(2) ?
C24 H24 . 0.9500 ?
C25 C30 . 1.410(3) ?
C25 C26 . 1.419(3) ?
C26 C27 . 1.368(3) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.401(3) ?
C28 C29 . 1.372(3) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.413(3) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.508(3) ?
C34 C35 . 1.387(3) ?
C34 C39 . 1.390(3) ?
C35 C36 . 1.385(3) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.376(4) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.380(4) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.384(3) ?
C38 H38 . 0.9500 ?
C39 H39 . 0.9500 ?
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
O1 H1B O5 . 0.84 1.87 2.681(2) 164.0 yes
O5 H5D O4 2_645 0.90(4) 1.85(4) 2.724(2) 163(3) yes
O5 H5E O3 . 0.77(3) 1.96(3) 2.724(2) 172(4) yes
O6 H6E N2 . 0.87 2.38 3.148(13) 146.5 yes
N1 H1 O4 2_645 1.00 1.64 2.643(2) 177.8 yes
C5 H5C Br1 2_745 0.98 3.09 3.910(2) 142.1 yes
C6 H6A O3 . 0.98 2.53 3.465(3) 160.6 yes
C6 H6B O6 1_455 0.98 2.28 3.249(13) 169.1 yes
C28 H28 O5 2_745 0.95 2.59 3.421(3) 145.5 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
C17 C1 C2 O1 . . . . 54.82(17) ?
C23 C1 C2 O1 . . . . -70.37(18) ?
C17 C1 C2 C3 . . . . 174.44(14) ?
C23 C1 C2 C3 . . . . 49.3(2) ?
C17 C1 C2 C7 . . . . -60.05(19) ?
C23 C1 C2 C7 . . . . 174.77(16) ?
O1 C2 C3 C4 . . . . -74.49(18) ?
C7 C2 C3 C4 . . . . 45.3(2) ?
C1 C2 C3 C4 . . . . 166.84(14) ?
C5 N1 C4 C3 . . . . 65.8(2) ?
C6 N1 C4 C3 . . . . -171.11(16) ?
C2 C3 C4 N1 . . . . 164.04(15) ?
O1 C2 C7 C8 . . . . -7.6(2) ?
C3 C2 C7 C8 . . . . -128.77(19) ?
C1 C2 C7 C8 . . . . 107.84(18) ?
O1 C2 C7 C16 . . . . 175.18(17) ?
C3 C2 C7 C16 . . . . 54.0(2) ?
C1 C2 C7 C16 . . . . -69.4(2) ?
C16 C7 C8 C9 . . . . 0.4(3) ?
C2 C7 C8 C9 . . . . -177.0(2) ?
C7 C8 C9 C10 . . . . -0.4(4) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
C9 C10 C11 C12 . . . . 179.7(3) ?
C9 C10 C11 C16 . . . . 0.3(3) ?
C10 C11 C12 C13 . . . . -179.6(3) ?
C16 C11 C12 C13 . . . . -0.2(4) ?
C11 C12 C13 C14 . . . . 0.3(5) ?
C12 C13 C14 C15 . . . . 0.5(5) ?
C13 C14 C15 C16 . . . . -1.4(4) ?
C14 C15 C16 C11 . . . . 1.4(3) ?
C14 C15 C16 C7 . . . . -179.7(2) ?
C10 C11 C16 C15 . . . . 178.8(2) ?
C12 C11 C16 C15 . . . . -0.6(3) ?
C10 C11 C16 C7 . . . . -0.2(3) ?
C12 C11 C16 C7 . . . . -179.6(2) ?
C8 C7 C16 C15 . . . . -179.1(2) ?
C2 C7 C16 C15 . . . . -1.9(3) ?
C8 C7 C16 C11 . . . . -0.2(3) ?
C2 C7 C16 C11 . . . . 177.02(17) ?
C23 C1 C17 C22 . . . . 46.1(2) ?
C2 C1 C17 C22 . . . . -82.5(2) ?
C23 C1 C17 C18 . . . . -134.71(18) ?
C2 C1 C17 C18 . . . . 96.7(2) ?
C22 C17 C18 C19 . . . . -0.5(3) ?
C1 C17 C18 C19 . . . . -179.7(2) ?
C17 C18 C19 C20 . . . . -0.2(4) ?
C18 C19 C20 C21 . . . . 1.1(4) ?
C19 C20 C21 C22 . . . . -1.3(4) ?
C20 C21 C22 C17 . . . . 0.7(3) ?
C18 C17 C22 C21 . . . . 0.2(3) ?
C1 C17 C22 C21 . . . . 179.44(19) ?
C17 C1 C23 C24 . . . . -87.3(2) ?
C2 C1 C23 C24 . . . . 38.7(2) ?
C17 C1 C23 C31 . . . . 86.83(19) ?
C2 C1 C23 C31 . . . . -147.14(16) ?
C31 C23 C24 C25 . . . . 2.7(3) ?
C1 C23 C24 C25 . . . . 177.00(17) ?
C23 C24 C25 C30 . . . . 1.8(3) ?
C23 C24 C25 C26 . . . . -177.98(18) ?
C30 C25 C26 C27 . . . . 1.3(3) ?
C24 C25 C26 C27 . . . . -178.92(18) ?
C25 C26 C27 C28 . . . . 1.7(3) ?
C25 C26 C27 Br1 . . . . -178.04(14) ?
C26 C27 C28 C29 . . . . -2.4(3) ?
Br1 C27 C28 C29 . . . . 177.34(17) ?
C27 C28 C29 C30 . . . . 0.0(3) ?
C31 N2 C30 C25 . . . . 1.8(3) ?
C31 N2 C30 C29 . . . . -179.23(19) ?
C24 C25 C30 N2 . . . . -4.3(3) ?
C26 C25 C30 N2 . . . . 175.47(18) ?
C24 C25 C30 C29 . . . . 176.72(18) ?
C26 C25 C30 C29 . . . . -3.5(3) ?
C28 C29 C30 N2 . . . . -176.2(2) ?
C28 C29 C30 C25 . . . . 2.8(3) ?
C30 N2 C31 O2 . . . . -175.89(17) ?
C30 N2 C31 C23 . . . . 3.4(3) ?
C32 O2 C31 N2 . . . . 3.0(3) ?
C32 O2 C31 C23 . . . . -176.38(18) ?
C24 C23 C31 N2 . . . . -5.7(3) ?
C1 C23 C31 N2 . . . . 179.65(18) ?
C24 C23 C31 O2 . . . . 173.63(16) ?
C1 C23 C31 O2 . . . . -1.1(2) ?
O3 C33 C34 C35 . . . . -169.4(2) ?
O4 C33 C34 C35 . . . . 9.7(3) ?
O3 C33 C34 C39 . . . . 9.6(3) ?
O4 C33 C34 C39 . . . . -171.3(2) ?
C39 C34 C35 C36 . . . . -1.2(4) ?
C33 C34 C35 C36 . . . . 177.8(3) ?
C34 C35 C36 C37 . . . . 0.6(5) ?
C35 C36 C37 C38 . . . . 0.1(5) ?
C36 C37 C38 C39 . . . . -0.1(5) ?
C37 C38 C39 C34 . . . . -0.5(5) ?
C35 C34 C39 C38 . . . . 1.1(4) ?
C33 C34 C39 C38 . . . . -177.9(3) ?

_cod_database_fobs_code 2022268
