#------------------------------------------------------------------------------
#$Date: 2021-03-27 08:13:50 +0200 (Sat, 27 Mar 2021) $
#$Revision: 263391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243790.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_2243790
loop_
_publ_author_name
'Zeller, Matthias'
'Bogdanowich-Knipp, Susan'
'Smith, Pamela'
'Purcell, Dale K.'
'Okezue, Mercy'
'Smith, Daniel T.'
'Byrn, Stephen R.'
'Clase, Kari L.'
_publ_section_title
;
 Maleate salts of bedaquiline
;
_journal_coeditor_code           TX2038
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              433
_journal_page_last               445
_journal_paper_doi               10.1107/S2056989021002991
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_iupac          '2C32 H32 Br N2 O2 +, 2C4 H3 O4 -, 3C4 H8 O'
_chemical_formula_moiety
'2(C32 H32 Br N2 O2), 2(C4 H3 O4), 3(C4 H8 O)'
_chemical_formula_sum            'C84 H94 Br2 N4 O15'
_chemical_formula_weight         1559.45
_chemical_name_common
;
Bedaquilinium maleate tetetrahydrofuran sesquihydrate
;
_chemical_name_systematic
;[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate tetrahydrofuran
sesquihydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.318(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.4119(6)
_cell_length_b                   13.5643(6)
_cell_length_c                   17.8475(8)
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      78.5760
_cell_measurement_theta_min      2.5929
_cell_volume                     3793.0(3)
_computing_cell_refinement
;
SAINT (Bruker, 2020)
;
_computing_data_collection
;
APEX3 (Bruker, 2020)
;
_computing_data_reduction
;
SAINT (Bruker, 2020)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b),
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 0.995
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest with PhotonIII_C14 CPAD
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18660
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.901
_diffrn_reflns_theta_min         2.593
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  0.3905
_exptl_absorpt_correction_T_min  0.2538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.521
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       0.00079(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7473
_refine_ls_number_restraints     223
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0538
_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)+6.5774P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1270
_reflns_number_gt                6615
_reflns_number_total             7473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           THF
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243790
_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   0.569
_shelx_estimated_absorpt_t_max   0.748
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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 0.26058(6) 0.03336(7) 0.44125(5) 0.0900(4) Uani d 1 . .
O O1 0.4801(2) 0.2596(2) 0.1676(2) 0.0393(8) Uani d 1 . .
H H1O 0.435393 0.274903 0.178628 0.047 Uiso calc 1 . .
O O2 0.5566(2) 0.4767(3) 0.3637(2) 0.0431(8) Uani d 1 . .
O O3 0.5052(2) 0.6774(3) 0.2100(2) 0.0474(9) Uani d 1 . .
O O4 0.5714(3) 0.6982(4) 0.1204(2) 0.0562(11) Uani d 1 . .
O O5 0.7069(3) 0.7612(4) 0.1131(2) 0.0580(11) Uani d 1 . .
H H5 0.636(5) 0.732(6) 0.121(4) 0.087 Uiso d 1 . .
O O6 0.8266(2) 0.8159(3) 0.1967(3) 0.0542(10) Uani d 1 . .
N N1 0.4013(2) 0.5583(3) 0.1018(2) 0.0354(9) Uani d 1 . .
H H1 0.438273 0.605699 0.139973 0.042 Uiso calc 1 . .
N N2 0.4546(3) 0.4009(3) 0.4074(2) 0.0393(9) Uani d 1 . .
C C1 0.5937(3) 0.3139(4) 0.2833(3) 0.0346(10) Uani d 1 . .
H H1A 0.629984 0.373327 0.302215 0.042 Uiso calc 1 . .
C C2 0.5429(3) 0.3346(3) 0.1955(3) 0.0347(10) Uani d 1 . .
C C3 0.4961(3) 0.4347(4) 0.1881(3) 0.0347(10) Uani d 1 . .
H H3A 0.452873 0.430504 0.216628 0.042 Uiso calc 1 . .
H H3B 0.537920 0.485963 0.214137 0.042 Uiso calc 1 . .
C C4 0.4524(3) 0.4665(4) 0.1047(3) 0.0375(11) Uani d 1 . .
H H4A 0.495996 0.478198 0.077433 0.045 Uiso calc 1 . .
H H4B 0.414420 0.413029 0.076740 0.045 Uiso calc 1 . .
C C5 0.3232(3) 0.5425(5) 0.1264(4) 0.0515(14) Uani d 1 . .
H H5A 0.288180 0.490667 0.093991 0.077 Uiso calc 1 . .
H H5B 0.290307 0.603851 0.119812 0.077 Uiso calc 1 . .
H H5C 0.339613 0.522452 0.181676 0.077 Uiso calc 1 . .
C C6 0.3793(4) 0.6057(4) 0.0235(3) 0.0452(12) Uani d 1 . .
H H6A 0.348841 0.558375 -0.016607 0.068 Uiso calc 1 . .
H H6B 0.431630 0.626946 0.012547 0.068 Uiso calc 1 . .
H H6C 0.342718 0.663002 0.022805 0.068 Uiso calc 1 . .
C C7 0.6027(3) 0.3295(4) 0.1431(3) 0.0356(10) Uani d 1 . .
C C8 0.5881(4) 0.2595(4) 0.0854(3) 0.0423(12) Uani d 1 . .
H H8 0.540722 0.216667 0.078641 0.051 Uiso calc 1 . .
C C9 0.6398(4) 0.2478(5) 0.0356(3) 0.0514(15) Uani d 1 . .
H H9 0.627396 0.197259 -0.002969 0.062 Uiso calc 1 . .
C C10 0.7074(4) 0.3088(5) 0.0429(3) 0.0525(15) Uani d 1 . .
H H10 0.741843 0.301365 0.008919 0.063 Uiso calc 1 . .
C C11 0.7262(3) 0.3826(5) 0.1004(3) 0.0454(13) Uani d 1 . .
C C12 0.7952(4) 0.4487(5) 0.1066(4) 0.0577(16) Uani d 1 . .
H H12 0.828900 0.440670 0.071970 0.069 Uiso calc 1 . .
C C13 0.8147(4) 0.5224(6) 0.1599(4) 0.0598(16) Uani d 1 . .
H H13 0.861375 0.565156 0.162841 0.072 Uiso calc 1 . .
C C14 0.7653(3) 0.5345(5) 0.2101(3) 0.0498(13) Uani d 1 . .
H H14 0.778767 0.586314 0.247614 0.060 Uiso calc 1 . .
C C15 0.6974(3) 0.4737(4) 0.2071(3) 0.0411(11) Uani d 1 . .
H H15 0.665097 0.484357 0.242605 0.049 Uiso calc 1 . .
C C16 0.6744(3) 0.3949(4) 0.1517(3) 0.0384(11) Uani d 1 . .
C C17 0.6542(3) 0.2269(4) 0.2958(3) 0.0376(11) Uani d 1 . .
C C18 0.6305(4) 0.1353(4) 0.2593(4) 0.0459(13) Uani d 1 . .
H H18 0.574583 0.126223 0.224728 0.055 Uiso calc 1 . .
C C19 0.6887(4) 0.0576(4) 0.2735(4) 0.0574(16) Uani d 1 . .
H H19 0.672835 -0.004031 0.248112 0.069 Uiso calc 1 . .
C C20 0.7703(4) 0.0711(5) 0.3255(4) 0.0644(19) Uani d 1 . .
H H20 0.809873 0.018029 0.335597 0.077 Uiso calc 1 . .
C C21 0.7936(4) 0.1583(6) 0.3613(4) 0.0618(17) Uani d 1 . .
H H21 0.849179 0.166675 0.396798 0.074 Uiso calc 1 . .
C C22 0.7358(3) 0.2363(5) 0.3460(3) 0.0488(14) Uani d 1 . .
H H22 0.753161 0.297922 0.371014 0.059 Uiso calc 1 . .
C C23 0.5332(3) 0.3070(4) 0.3332(3) 0.0341(10) Uani d 1 . .
C C24 0.4933(3) 0.2239(4) 0.3446(3) 0.0383(11) Uani d 1 . .
H H24 0.506052 0.163620 0.323478 0.046 Uiso calc 1 . .
C C25 0.4326(3) 0.2237(4) 0.3873(3) 0.0403(12) Uani d 1 . .
C C26 0.3881(4) 0.1378(5) 0.3977(3) 0.0494(14) Uani d 1 . .
H H26 0.400808 0.075482 0.379555 0.059 Uiso calc 1 . .
C C27 0.3263(4) 0.1467(6) 0.4344(4) 0.0595(17) Uani d 1 . .
C C28 0.3074(4) 0.2364(6) 0.4640(3) 0.0587(17) Uani d 1 . .
H H28 0.264857 0.239537 0.490240 0.070 Uiso calc 1 . .
C C29 0.3505(3) 0.3197(5) 0.4551(3) 0.0513(14) Uani d 1 . .
H H29 0.337974 0.380839 0.475108 0.062 Uiso calc 1 . .
C C30 0.4137(3) 0.3149(4) 0.4161(3) 0.0415(12) Uani d 1 . .
C C31 0.5119(3) 0.3938(4) 0.3702(3) 0.0369(11) Uani d 1 . .
C C32 0.5344(5) 0.5659(4) 0.3965(4) 0.0616(17) Uani d 1 . .
H H32A 0.475980 0.584984 0.367499 0.092 Uiso calc 1 . .
H H32B 0.573882 0.618559 0.392727 0.092 Uiso calc 1 . .
H H32C 0.538402 0.554867 0.451767 0.092 Uiso calc 1 . .
C C33 0.5672(3) 0.7063(4) 0.1903(3) 0.0399(11) Uani d 1 . .
C C34 0.6399(3) 0.7506(4) 0.2525(3) 0.0438(12) Uani d 1 . .
H H34 0.631293 0.755572 0.302730 0.053 Uiso calc 1 . .
C C35 0.7151(3) 0.7844(4) 0.2489(3) 0.0419(12) Uani d 1 . .
H H35 0.750474 0.811123 0.296725 0.050 Uiso calc 1 . .
C C36 0.7533(3) 0.7875(4) 0.1829(3) 0.0423(12) Uani d 1 . .
O O7 0.4370(6) 0.0263(8) 0.0209(6) 0.075(3) Uani d 0.5 A -1
C C37 0.5084(18) -0.034(3) 0.0604(14) 0.100(10) Uani d 0.5 A -1
H H37A 0.552048 0.006461 0.097766 0.120 Uiso calc 0.5 A -1
H H37B 0.489509 -0.086055 0.090748 0.120 Uiso calc 0.5 A -1
C C38 0.5450(14) -0.080(2) 0.0055(13) 0.128(8) Uani d 0.5 A -1
H H38A 0.537402 -0.152082 0.004958 0.154 Uiso calc 0.5 A -1
H H38B 0.606666 -0.064579 0.018760 0.154 Uiso calc 0.5 A -1
C C39 0.4956(13) -0.034(2) -0.0747(14) 0.073(6) Uani d 0.5 A -1
H H39A 0.525268 0.023994 -0.087447 0.087 Uiso calc 0.5 A -1
H H39B 0.485523 -0.083061 -0.117722 0.087 Uiso calc 0.5 A -1
C C40 0.4133(8) -0.0059(9) -0.0577(8) 0.059(3) Uani d 0.5 A -1
H H40A 0.383893 0.047510 -0.093328 0.071 Uiso calc 0.5 A -1
H H40B 0.374534 -0.063351 -0.064957 0.071 Uiso calc 0.5 A -1
O O8 1.0606(9) 0.3358(13) 0.4220(9) 0.126(5) Uani d 0.587(16) B 1
C C41 0.9722(12) 0.3162(15) 0.3956(11) 0.094(5) Uani d 0.587(16) B 1
H H41A 0.944248 0.347343 0.431763 0.113 Uiso calc 0.587(16) B 1
H H41B 0.962618 0.244206 0.396135 0.113 Uiso calc 0.587(16) B 1
C C42 0.9349(11) 0.3530(12) 0.3185(9) 0.082(4) Uani d 0.587(16) B 1
H H42A 0.881218 0.388515 0.315266 0.099 Uiso calc 0.587(16) B 1
H H42B 0.921747 0.298130 0.280234 0.099 Uiso calc 0.587(16) B 1
C C43 0.9983(11) 0.4216(12) 0.3012(10) 0.078(4) Uani d 0.587(16) B 1
H H43A 0.971975 0.486075 0.282200 0.093 Uiso calc 0.587(16) B 1
H H43B 1.022812 0.393146 0.261618 0.093 Uiso calc 0.587(16) B 1
C C44 1.0658(12) 0.4317(14) 0.3806(11) 0.090(5) Uani d 0.587(16) B 1
H H44A 1.123155 0.440687 0.374167 0.108 Uiso calc 0.587(16) B 1
H H44B 1.053089 0.488380 0.410245 0.108 Uiso calc 0.587(16) B 1
O O8B 0.9965(13) 0.4595(16) 0.3290(13) 0.108(6) Uani d 0.413(16) B 2
C C41B 1.0619(16) 0.4729(15) 0.4031(15) 0.082(6) Uani d 0.413(16) B 2
H H41C 1.108737 0.513132 0.394742 0.098 Uiso calc 0.413(16) B 2
H H41D 1.037590 0.509340 0.439597 0.098 Uiso calc 0.413(16) B 2
C C42B 1.0957(17) 0.3804(15) 0.4381(15) 0.094(6) Uani d 0.413(16) B 2
H H42C 1.108883 0.382041 0.495929 0.112 Uiso calc 0.413(16) B 2
H H42D 1.147525 0.361285 0.424051 0.112 Uiso calc 0.413(16) B 2
C C43B 1.018(2) 0.3092(17) 0.3993(18) 0.098(6) Uani d 0.413(16) B 2
H H43C 1.035681 0.256696 0.368663 0.117 Uiso calc 0.413(16) B 2
H H43D 0.996716 0.278165 0.439884 0.117 Uiso calc 0.413(16) B 2
C C44B 0.9520(17) 0.374(2) 0.347(2) 0.115(6) Uani d 0.413(16) B 2
H H44C 0.921533 0.338300 0.298283 0.138 Uiso calc 0.413(16) B 2
H H44D 0.909914 0.394339 0.373839 0.138 Uiso calc 0.413(16) B 2
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'
Br Br -0.6763 1.2805 '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 H1O . . 109.5 ?
C31 O2 C32 . . 116.8(4) ?
C33 O4 H5 . . 106(4) ?
C36 O5 H5 . . 106(3) ?
C6 N1 C5 . . 110.5(4) ?
C6 N1 C4 . . 111.8(4) ?
C5 N1 C4 . . 113.2(4) ?
C6 N1 H1 . . 107.0 ?
C5 N1 H1 . . 107.0 ?
C4 N1 H1 . . 107.0 ?
C31 N2 C30 . . 116.4(5) ?
C17 C1 C23 . . 112.3(4) ?
C17 C1 C2 . . 114.7(4) ?
C23 C1 C2 . . 110.6(4) ?
C17 C1 H1A . . 106.2 ?
C23 C1 H1A . . 106.2 ?
C2 C1 H1A . . 106.2 ?
O1 C2 C7 . . 106.3(4) ?
O1 C2 C3 . . 107.9(4) ?
C7 C2 C3 . . 112.1(4) ?
O1 C2 C1 . . 109.5(4) ?
C7 C2 C1 . . 110.6(4) ?
C3 C2 C1 . . 110.2(4) ?
C4 C3 C2 . . 114.4(4) ?
C4 C3 H3A . . 108.7 ?
C2 C3 H3A . . 108.7 ?
C4 C3 H3B . . 108.7 ?
C2 C3 H3B . . 108.7 ?
H3A C3 H3B . . 107.6 ?
N1 C4 C3 . . 111.7(4) ?
N1 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
N1 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 107.9 ?
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 . . 117.5(5) ?
C8 C7 C2 . . 119.1(5) ?
C16 C7 C2 . . 123.5(4) ?
C7 C8 C9 . . 123.4(6) ?
C7 C8 H8 . . 118.3 ?
C9 C8 H8 . . 118.3 ?
C10 C9 C8 . . 119.9(6) ?
C10 C9 H9 . . 120.0 ?
C8 C9 H9 . . 120.0 ?
C9 C10 C11 . . 120.1(5) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C10 C11 C12 . . 120.3(5) ?
C10 C11 C16 . . 120.5(5) ?
C12 C11 C16 . . 119.1(5) ?
C13 C12 C11 . . 122.5(6) ?
C13 C12 H12 . . 118.7 ?
C11 C12 H12 . . 118.7 ?
C12 C13 C14 . . 118.8(6) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.8(6) ?
C15 C14 H14 . . 119.1 ?
C13 C14 H14 . . 119.1 ?
C14 C15 C16 . . 121.3(5) ?
C14 C15 H15 . . 119.3 ?
C16 C15 H15 . . 119.3 ?
C15 C16 C11 . . 116.4(5) ?
C15 C16 C7 . . 125.0(5) ?
C11 C16 C7 . . 118.6(5) ?
C22 C17 C18 . . 117.7(5) ?
C22 C17 C1 . . 119.4(5) ?
C18 C17 C1 . . 122.8(5) ?
C19 C18 C17 . . 120.4(5) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C18 C19 C20 . . 119.5(6) ?
C18 C19 H19 . . 120.3 ?
C20 C19 H19 . . 120.3 ?
C21 C20 C19 . . 120.8(6) ?
C21 C20 H20 . . 119.6 ?
C19 C20 H20 . . 119.6 ?
C20 C21 C22 . . 119.6(6) ?
C20 C21 H21 . . 120.2 ?
C22 C21 H21 . . 120.2 ?
C17 C22 C21 . . 122.0(6) ?
C17 C22 H22 . . 119.0 ?
C21 C22 H22 . . 119.0 ?
C24 C23 C31 . . 114.7(4) ?
C24 C23 C1 . . 124.8(5) ?
C31 C23 C1 . . 120.5(4) ?
C23 C24 C25 . . 122.1(5) ?
C23 C24 H24 . . 119.0 ?
C25 C24 H24 . . 119.0 ?
C30 C25 C26 . . 119.7(5) ?
C30 C25 C24 . . 117.4(5) ?
C26 C25 C24 . . 122.8(5) ?
C27 C26 C25 . . 118.4(6) ?
C27 C26 H26 . . 120.8 ?
C25 C26 H26 . . 120.8 ?
C26 C27 C28 . . 122.6(6) ?
C26 C27 Br1 . . 118.4(6) ?
C28 C27 Br1 . . 119.0(5) ?
C29 C28 C27 . . 119.6(6) ?
C29 C28 H28 . . 120.2 ?
C27 C28 H28 . . 120.2 ?
C28 C29 C30 . . 120.1(6) ?
C28 C29 H29 . . 119.9 ?
C30 C29 H29 . . 119.9 ?
N2 C30 C25 . . 122.2(5) ?
N2 C30 C29 . . 118.2(5) ?
C25 C30 C29 . . 119.6(5) ?
N2 C31 O2 . . 117.9(5) ?
N2 C31 C23 . . 127.0(5) ?
O2 C31 C23 . . 115.0(4) ?
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 . . 122.7(5) ?
O3 C33 C34 . . 117.4(5) ?
O4 C33 C34 . . 119.9(5) ?
C35 C34 C33 . . 130.3(5) ?
C35 C34 H34 . . 114.8 ?
C33 C34 H34 . . 114.8 ?
C34 C35 C36 . . 131.3(5) ?
C34 C35 H35 . . 114.4 ?
C36 C35 H35 . . 114.4 ?
O6 C36 O5 . . 122.8(5) ?
O6 C36 C35 . . 118.1(5) ?
O5 C36 C35 . . 119.1(4) ?
C40 O7 C37 . . 104.8(14) ?
C38 C37 O7 . . 110.9(16) ?
C38 C37 H37A . . 109.5 ?
O7 C37 H37A . . 109.5 ?
C38 C37 H37B . . 109.5 ?
O7 C37 H37B . . 109.5 ?
H37A C37 H37B . . 108.0 ?
C37 C38 C39 . . 104.5(13) ?
C37 C38 H38A . . 110.8 ?
C39 C38 H38A . . 110.8 ?
C37 C38 H38B . . 110.8 ?
C39 C38 H38B . . 110.8 ?
H38A C38 H38B . . 108.9 ?
C40 C39 C38 . . 99.7(15) ?
C40 C39 H39A . . 111.8 ?
C38 C39 H39A . . 111.8 ?
C40 C39 H39B . . 111.8 ?
C38 C39 H39B . . 111.8 ?
H39A C39 H39B . . 109.6 ?
O7 C40 C39 . . 106.2(13) ?
O7 C40 H40A . . 110.5 ?
C39 C40 H40A . . 110.5 ?
O7 C40 H40B . . 110.5 ?
C39 C40 H40B . . 110.5 ?
H40A C40 H40B . . 108.7 ?
C41 O8 C44 . . 101.6(13) ?
O8 C41 C42 . . 111.1(14) ?
O8 C41 H41A . . 109.4 ?
C42 C41 H41A . . 109.4 ?
O8 C41 H41B . . 109.4 ?
C42 C41 H41B . . 109.4 ?
H41A C41 H41B . . 108.0 ?
C41 C42 C43 . . 107.0(12) ?
C41 C42 H42A . . 110.3 ?
C43 C42 H42A . . 110.3 ?
C41 C42 H42B . . 110.3 ?
C43 C42 H42B . . 110.3 ?
H42A C42 H42B . . 108.6 ?
C42 C43 C44 . . 102.8(13) ?
C42 C43 H43A . . 111.2 ?
C44 C43 H43A . . 111.2 ?
C42 C43 H43B . . 111.2 ?
C44 C43 H43B . . 111.2 ?
H43A C43 H43B . . 109.1 ?
O8 C44 C43 . . 104.2(13) ?
O8 C44 H44A . . 110.9 ?
C43 C44 H44A . . 110.9 ?
O8 C44 H44B . . 110.9 ?
C43 C44 H44B . . 110.9 ?
H44A C44 H44B . . 108.9 ?
C41B O8B C44B . . 100.5(16) ?
C42B C41B O8B . . 111.9(16) ?
C42B C41B H41C . . 109.2 ?
O8B C41B H41C . . 109.2 ?
C42B C41B H41D . . 109.2 ?
O8B C41B H41D . . 109.2 ?
H41C C41B H41D . . 107.9 ?
C41B C42B C43B . . 100.8(16) ?
C41B C42B H42C . . 111.6 ?
C43B C42B H42C . . 111.6 ?
C41B C42B H42D . . 111.6 ?
C43B C42B H42D . . 111.6 ?
H42C C42B H42D . . 109.4 ?
C44B C43B C42B . . 104.9(17) ?
C44B C43B H43C . . 110.8 ?
C42B C43B H43C . . 110.8 ?
C44B C43B H43D . . 110.8 ?
C42B C43B H43D . . 110.8 ?
H43C C43B H43D . . 108.8 ?
O8B C44B C43B . . 106.7(18) ?
O8B C44B H44C . . 110.4 ?
C43B C44B H44C . . 110.4 ?
O8B C44B H44D . . 110.4 ?
C43B C44B H44D . . 110.4 ?
H44C C44B H44D . . 108.6 ?
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 . 1.903(6) ?
O1 C2 . 1.427(5) ?
O1 H1O . 0.8400 ?
O2 C31 . 1.367(6) ?
O2 C32 . 1.437(7) ?
O3 C33 . 1.234(6) ?
O4 C33 . 1.275(7) ?
O4 H5 . 1.15(8) ?
O5 C36 . 1.301(6) ?
O5 H5 . 1.28(8) ?
O6 C36 . 1.217(6) ?
N1 C6 . 1.482(7) ?
N1 C5 . 1.490(6) ?
N1 C4 . 1.493(6) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.305(6) ?
N2 C30 . 1.378(7) ?
C1 C17 . 1.516(7) ?
C1 C23 . 1.521(7) ?
C1 C2 . 1.566(7) ?
C1 H1A . 1.0000 ?
C2 C7 . 1.545(7) ?
C2 C3 . 1.546(6) ?
C3 C4 . 1.511(7) ?
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 . 1.368(7) ?
C7 C16 . 1.444(7) ?
C8 C9 . 1.408(8) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.359(9) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.400(9) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.423(9) ?
C11 C16 . 1.435(7) ?
C12 C13 . 1.351(10) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.385(8) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.375(8) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.428(8) ?
C15 H15 . 0.9500 ?
C17 C22 . 1.378(7) ?
C17 C18 . 1.402(8) ?
C18 C19 . 1.393(8) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.396(9) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.345(10) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.393(8) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.349(7) ?
C23 C31 . 1.443(7) ?
C24 C25 . 1.422(7) ?
C24 H24 . 0.9500 ?
C25 C30 . 1.409(8) ?
C25 C26 . 1.418(8) ?
C26 C27 . 1.365(9) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.399(10) ?
C28 C29 . 1.367(9) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.411(8) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.493(7) ?
C34 C35 . 1.337(8) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.490(8) ?
C35 H35 . 0.9500 ?
O7 C40 . 1.408(15) ?
O7 C37 . 1.43(2) ?
C37 C38 . 1.43(2) ?
C37 H37A . 0.9900 ?
C37 H37B . 0.9900 ?
C38 C39 . 1.55(2) ?
C38 H38A . 0.9900 ?
C38 H38B . 0.9900 ?
C39 C40 . 1.52(2) ?
C39 H39A . 0.9900 ?
C39 H39B . 0.9900 ?
C40 H40A . 0.9900 ?
C40 H40B . 0.9900 ?
O8 C41 . 1.411(17) ?
O8 C44 . 1.510(18) ?
C41 C42 . 1.42(2) ?
C41 H41A . 0.9900 ?
C41 H41B . 0.9900 ?
C42 C43 . 1.494(19) ?
C42 H42A . 0.9900 ?
C42 H42B . 0.9900 ?
C43 C44 . 1.523(19) ?
C43 H43A . 0.9900 ?
C43 H43B . 0.9900 ?
C44 H44A . 0.9900 ?
C44 H44B . 0.9900 ?
O8B C41B . 1.45(2) ?
O8B C44B . 1.46(2) ?
C41B C42B . 1.44(2) ?
C41B H41C . 0.9900 ?
C41B H41D . 0.9900 ?
C42B C43B . 1.58(2) ?
C42B H42C . 0.9900 ?
C42B H42D . 0.9900 ?
C43B C44B . 1.49(2) ?
C43B H43C . 0.9900 ?
C43B H43D . 0.9900 ?
C44B H44C . 0.9900 ?
C44B H44D . 0.9900 ?
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 H1O O6 3_445 0.84 1.99 2.824(5) 175.7 yes
O4 H5 O5 . 1.15(8) 1.28(8) 2.422(5) 171(7) yes
N1 H1 O3 . 1.00 1.70 2.699(5) 174.8 yes
N1 H1 O4 . 1.00 2.63 3.310(6) 125.1 yes
C3 H3A O6 3_445 0.99 2.53 3.258(6) 130.2 yes
C3 H3B O3 . 0.99 2.65 3.314(6) 124.7 yes
C6 H6B O4 2_655 0.98 2.55 3.173(7) 121.5 yes
C26 H26 O8B 3_445 0.95 2.57 3.44(3) 152.1 yes
C42 H42B O3 3_545 0.99 2.67 3.478(17) 138.4 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_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 . . . . 71.7(5) ?
C23 C1 C2 O1 . . . . -56.5(5) ?
C17 C1 C2 C7 . . . . -45.2(5) ?
C23 C1 C2 C7 . . . . -173.4(4) ?
C17 C1 C2 C3 . . . . -169.8(4) ?
C23 C1 C2 C3 . . . . 62.0(5) ?
O1 C2 C3 C4 . . . . -66.4(5) ?
C7 C2 C3 C4 . . . . 50.4(5) ?
C1 C2 C3 C4 . . . . 174.1(4) ?
C6 N1 C4 C3 . . . . 163.5(4) ?
C5 N1 C4 C3 . . . . -70.9(5) ?
C2 C3 C4 N1 . . . . 174.3(4) ?
O1 C2 C7 C8 . . . . -1.2(6) ?
C3 C2 C7 C8 . . . . -118.9(5) ?
C1 C2 C7 C8 . . . . 117.6(5) ?
O1 C2 C7 C16 . . . . 179.0(4) ?
C3 C2 C7 C16 . . . . 61.3(6) ?
C1 C2 C7 C16 . . . . -62.1(6) ?
C16 C7 C8 C9 . . . . 0.9(8) ?
C2 C7 C8 C9 . . . . -178.9(5) ?
C7 C8 C9 C10 . . . . -1.0(8) ?
C8 C9 C10 C11 . . . . 0.7(8) ?
C9 C10 C11 C12 . . . . -178.0(5) ?
C9 C10 C11 C16 . . . . -0.4(8) ?
C10 C11 C12 C13 . . . . 178.4(6) ?
C16 C11 C12 C13 . . . . 0.8(9) ?
C11 C12 C13 C14 . . . . -0.4(10) ?
C12 C13 C14 C15 . . . . 0.0(9) ?
C13 C14 C15 C16 . . . . -0.1(8) ?
C14 C15 C16 C11 . . . . 0.5(7) ?
C14 C15 C16 C7 . . . . -178.1(5) ?
C10 C11 C16 C15 . . . . -178.5(5) ?
C12 C11 C16 C15 . . . . -0.8(7) ?
C10 C11 C16 C7 . . . . 0.3(8) ?
C12 C11 C16 C7 . . . . 177.9(5) ?
C8 C7 C16 C15 . . . . 178.1(5) ?
C2 C7 C16 C15 . . . . -2.2(8) ?
C8 C7 C16 C11 . . . . -0.5(7) ?
C2 C7 C16 C11 . . . . 179.2(5) ?
C23 C1 C17 C22 . . . . -98.2(5) ?
C2 C1 C17 C22 . . . . 134.4(5) ?
C23 C1 C17 C18 . . . . 80.6(6) ?
C2 C1 C17 C18 . . . . -46.7(7) ?
C22 C17 C18 C19 . . . . -0.6(8) ?
C1 C17 C18 C19 . . . . -179.4(5) ?
C17 C18 C19 C20 . . . . 1.1(9) ?
C18 C19 C20 C21 . . . . -0.6(10) ?
C19 C20 C21 C22 . . . . -0.4(11) ?
C18 C17 C22 C21 . . . . -0.4(9) ?
C1 C17 C22 C21 . . . . 178.5(5) ?
C20 C21 C22 C17 . . . . 0.9(10) ?
C17 C1 C23 C24 . . . . -42.3(6) ?
C2 C1 C23 C24 . . . . 87.2(6) ?
C17 C1 C23 C31 . . . . 140.2(5) ?
C2 C1 C23 C31 . . . . -90.3(5) ?
C31 C23 C24 C25 . . . . 2.3(7) ?
C1 C23 C24 C25 . . . . -175.3(4) ?
C23 C24 C25 C30 . . . . 1.6(7) ?
C23 C24 C25 C26 . . . . 177.9(5) ?
C30 C25 C26 C27 . . . . 1.3(8) ?
C24 C25 C26 C27 . . . . -175.0(5) ?
C25 C26 C27 C28 . . . . -2.0(9) ?
C25 C26 C27 Br1 . . . . 175.3(4) ?
C26 C27 C28 C29 . . . . 1.4(10) ?
Br1 C27 C28 C29 . . . . -175.9(4) ?
C27 C28 C29 C30 . . . . 0.0(9) ?
C31 N2 C30 C25 . . . . 0.4(7) ?
C31 N2 C30 C29 . . . . -179.2(5) ?
C26 C25 C30 N2 . . . . -179.6(5) ?
C24 C25 C30 N2 . . . . -3.2(7) ?
C26 C25 C30 C29 . . . . 0.0(7) ?
C24 C25 C30 C29 . . . . 176.5(5) ?
C28 C29 C30 N2 . . . . 179.0(5) ?
C28 C29 C30 C25 . . . . -0.7(8) ?
C30 N2 C31 O2 . . . . -177.0(4) ?
C30 N2 C31 C23 . . . . 4.2(7) ?
C32 O2 C31 N2 . . . . -1.8(7) ?
C32 O2 C31 C23 . . . . 177.2(5) ?
C24 C23 C31 N2 . . . . -5.6(7) ?
C1 C23 C31 N2 . . . . 172.1(5) ?
C24 C23 C31 O2 . . . . 175.6(4) ?
C1 C23 C31 O2 . . . . -6.7(6) ?
O3 C33 C34 C35 . . . . 177.4(6) ?
O4 C33 C34 C35 . . . . -1.5(9) ?
C33 C34 C35 C36 . . . . -1.7(10) ?
C34 C35 C36 O6 . . . . -174.5(6) ?
C34 C35 C36 O5 . . . . 6.4(9) ?
C40 O7 C37 C38 . . . . 18(3) ?
O7 C37 C38 C39 . . . . 5(3) ?
C37 C38 C39 C40 . . . . -25(3) ?
C37 O7 C40 C39 . . . . -35(2) ?
C38 C39 C40 O7 . . . . 37(2) ?
C44 O8 C41 C42 . . . . 32(2) ?
O8 C41 C42 C43 . . . . -14(2) ?
C41 C42 C43 C44 . . . . -9.4(19) ?
C41 O8 C44 C43 . . . . -36(2) ?
C42 C43 C44 O8 . . . . 27.9(18) ?
C44B O8B C41B C42B . . . . 39(3) ?
O8B C41B C42B C43B . . . . -25(3) ?
C41B C42B C43B C44B . . . . 0(4) ?
C41B O8B C44B C43B . . . . -37(3) ?
C42B C43B C44B O8B . . . . 23(4) ?

_cod_database_fobs_code 2243790
