#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/31/7103198.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_7103198
loop_
_publ_author_name
'Bertelsen, Søren'
'Johansen, Rasmus L'
'Jørgensen, Karl Anker'
_publ_section_title
;
 Controlling the formation of 1 out of 64 stereoisomers using
 organocatalysis.
;
_journal_issue                   26
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3016
_journal_page_last               3018
_journal_paper_doi               10.1039/b806418k
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H25 Br1 O10'
_chemical_formula_sum            'C23 H25 Br O10'
_chemical_formula_weight         541.34
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      18
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2008-05-08T14:00:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9402(7)
_cell_length_b                   15.9657(7)
_cell_length_c                   18.6847(7)
_cell_measurement_reflns_used    6022
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      2.5
_cell_measurement_wavelength     0.71073
_cell_volume                     4755.2(3)
_computing_cell_refinement       'Saint+ (Bruker-Nonius, 2007)'
_computing_data_collection       'Apex2 (Bruker-Nonius, 2007)'
_computing_data_reduction        'Saint+ (Bruker-Nonius, 2007)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 12.00
_diffrn_detector_type            'APEX2 charged-coupled device'
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker X8 APEX-II diffractometer'
_diffrn_measurement_method
;
Narrow slices collected using φ- and ω-scans
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.035
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16293
_diffrn_reflns_theta_full        21.73
_diffrn_reflns_theta_max         21.73
_diffrn_reflns_theta_min         3.06
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.784
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Sheldrick, 2004)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.421
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.010(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     617
_refine_ls_number_reflns         5237
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.0329
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0427P)²+1.4756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                4524
_reflns_number_total             5237
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b806418k.txt
_cod_data_source_block           08jo0010_0m
_cod_database_code               7103198
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6465(4) 1.0505(3) -0.1205(3) 0.0844(17) Uani 1 1 d . . .
H1A H 0.6801 1.0787 -0.1556 0.127 Uiso 1 1 calc R . .
H1B H 0.6411 1.0852 -0.0788 0.127 Uiso 1 1 calc R . .
H1C H 0.5919 1.0394 -0.14 0.127 Uiso 1 1 calc R . .
C2 C 0.5488(4) 1.1155(4) 0.3199(3) 0.117(2) Uani 1 1 d . . .
H2A H 0.523 1.1646 0.3 0.176 Uiso 1 1 calc R . .
H2B H 0.5066 1.0742 0.3296 0.176 Uiso 1 1 calc R . .
H2C H 0.5887 1.0933 0.2864 0.176 Uiso 1 1 calc R . .
C3 C 1.0518(3) 1.1474(6) 0.6318(5) 0.183(5) Uani 1 1 d . . .
H3A H 1.0835 1.1706 0.6708 0.274 Uiso 1 1 calc R . .
H3B H 1.0842 1.1508 0.5886 0.274 Uiso 1 1 calc R . .
H3C H 1.0389 1.0898 0.6418 0.274 Uiso 1 1 calc R . .
C2A C 0.5480(2) 0.7652(2) -0.0652(2) 0.0365(10) Uani 1 1 d . . .
H001 H 0.5251 0.8214 -0.0574 0.044 Uiso 1 1 calc R . .
C009 C 0.5892(2) 0.6685(2) 0.0333(2) 0.0384(10) Uani 1 1 d . . .
C012 C 0.5313(2) 0.7135(2) 0.0000(2) 0.0378(10) Uani 1 1 d . . .
C013 C 0.7290(2) 0.7364(2) 0.0519(2) 0.0375(10) Uani 1 1 d . . .
H01A H 0.7873 0.736 0.0371 0.045 Uiso 1 1 calc R . .
H01B H 0.727 0.7229 0.1025 0.045 Uiso 1 1 calc R . .
C6A C 0.6921(2) 0.8244(2) 0.0399(2) 0.0364(10) Uani 1 1 d . . .
H015 H 0.6344 0.8238 0.058 0.044 Uiso 1 1 calc R . .
C016 C 0.7305(3) 1.0152(3) 0.6449(3) 0.0491(12) Uani 1 1 d . . .
C018 C 0.7365(2) 1.2428(2) 0.4662(2) 0.0365(10) Uani 1 1 d . . .
H01C H 0.7334 1.3007 0.4817 0.044 Uiso 1 1 calc R . .
H01D H 0.724 1.2411 0.4154 0.044 Uiso 1 1 calc R . .
C6B C 0.8254(2) 1.2093(2) 0.4790(2) 0.0356(10) Uani 1 1 d . . .
H019 H 0.8273 1.152 0.4602 0.043 Uiso 1 1 calc R . .
C4A C 0.6849(2) 0.6895(2) -0.0699(2) 0.0357(10) Uani 1 1 d . . .
H021 H 0.6507 0.647 -0.094 0.043 Uiso 1 1 calc R . .
C1A C 0.6423(2) 0.7736(2) -0.08399(19) 0.0343(10) Uani 1 1 d . . .
C023 C 0.7719(3) 0.6829(3) -0.1017(2) 0.0444(11) Uani 1 1 d . . .
C5A C 0.6879(2) 0.8430(2) -0.0400(2) 0.0363(10) Uani 1 1 d . . .
H024 H 0.7456 0.8467 -0.0578 0.044 Uiso 1 1 calc R . .
C027 C 0.5004(3) 0.7246(3) -0.1269(2) 0.0407(10) Uani 1 1 d . . .
C028 C 0.6464(3) 0.9273(3) -0.0527(2) 0.0447(11) Uani 1 1 d . . .
C031 C 0.9280(2) 1.3288(3) 0.4640(3) 0.0539(12) Uani 1 1 d . . .
H031 H 0.9231 1.3404 0.5126 0.065 Uiso 1 1 calc R . .
C032 C 0.8865(2) 1.2609(3) 0.4355(2) 0.0428(11) Uani 1 1 d . . .
C3B C 0.6717(2) 1.1912(2) 0.5067(2) 0.0363(10) Uani 1 1 d . . .
H034 H 0.6159 1.2144 0.4972 0.044 Uiso 1 1 calc R . .
C035 C 0.6129(4) 0.5466(3) 0.1985(3) 0.0846(17) Uani 1 1 d . . .
H03A H 0.6638 0.5223 0.2165 0.127 Uiso 1 1 calc R . .
H03B H 0.5721 0.5032 0.1911 0.127 Uiso 1 1 calc R . .
H03C H 0.5916 0.5863 0.2326 0.127 Uiso 1 1 calc R . .
C036 C 0.7402(2) 0.8875(2) 0.0833(2) 0.0376(10) Uani 1 1 d . . .
C038 C 0.8376(4) 0.9929(3) 0.1690(3) 0.0674(15) Uani 1 1 d . . .
H038 H 0.8702 1.0283 0.197 0.081 Uiso 1 1 calc R . .
C2B C 0.7696(2) 1.0643(2) 0.5841(2) 0.0411(10) Uani 1 1 d . . .
H039 H 0.8268 1.0434 0.577 0.049 Uiso 1 1 calc R . .
C040 C 0.6309(3) 1.0752(3) 0.4184(3) 0.0595(13) Uani 1 1 d . . .
C042 C 0.6730(2) 1.1017(3) 0.4834(2) 0.0426(11) Uani 1 1 d . . .
C4B C 0.6895(2) 1.1978(3) 0.5867(2) 0.0423(11) Uani 1 1 d . . .
H043 H 0.6473 1.164 0.6117 0.051 Uiso 1 1 calc R . .
C044 C 0.7207(3) 1.0460(3) 0.5180(2) 0.0453(11) Uani 1 1 d . . .
C045 C 0.9297(3) 1.1629(4) 0.5702(3) 0.0710(17) Uani 1 1 d . . .
C046 C 0.9434(3) 1.2961(4) 0.3196(3) 0.0729(15) Uani 1 1 d . . .
H046 H 0.9477 1.285 0.2708 0.088 Uiso 1 1 calc R . .
C047 C 0.8124(3) 0.9248(2) 0.0579(2) 0.0455(11) Uani 1 1 d . . .
H047 H 0.8288 0.9151 0.0108 0.055 Uiso 1 1 calc R . .
C048 C 0.3893(3) 0.7429(3) -0.2077(2) 0.0581(13) Uani 1 1 d . . .
H04A H 0.3504 0.7851 -0.2232 0.087 Uiso 1 1 calc R . .
H04B H 0.3589 0.696 -0.1887 0.087 Uiso 1 1 calc R . .
H04C H 0.4225 0.7248 -0.2477 0.087 Uiso 1 1 calc R . .
C049 C 0.7663(3) 0.9579(3) 0.1967(3) 0.0624(13) Uani 1 1 d . . .
H049 H 0.7502 0.9691 0.2436 0.075 Uiso 1 1 calc R . .
C050 C 0.7486(3) 0.8984(3) 0.7207(3) 0.0728(15) Uani 1 1 d . . .
H05A H 0.7905 0.8579 0.7334 0.109 Uiso 1 1 calc R . .
H05B H 0.7004 0.8702 0.7014 0.109 Uiso 1 1 calc R . .
H05C H 0.7325 0.9295 0.7624 0.109 Uiso 1 1 calc R . .
C1B C 0.7752(2) 1.1591(3) 0.6022(2) 0.0403(10) Uani 1 1 d . . .
C053 C 0.8965(3) 0.6037(3) -0.1025(3) 0.0679(14) Uani 1 1 d . . .
H05D H 0.9215 0.5581 -0.0768 0.102 Uiso 1 1 calc R . .
H05E H 0.9318 0.6522 -0.0988 0.102 Uiso 1 1 calc R . .
H05F H 0.8904 0.5885 -0.152 0.102 Uiso 1 1 calc R . .
C3A C 0.6805(2) 0.6701(2) 0.0097(2) 0.0373(10) Uani 1 1 d . . .
H054 H 0.7056 0.615 0.0184 0.045 Uiso 1 1 calc R . .
C055 C 0.5659(3) 0.6238(3) 0.0984(2) 0.0500(12) Uani 1 1 d . . .
C056 C 0.5934(4) 1.4057(3) 0.6141(3) 0.0931(19) Uani 1 1 d . . .
H05G H 0.5405 1.4232 0.5946 0.14 Uiso 1 1 calc R . .
H05H H 0.6369 1.4426 0.5977 0.14 Uiso 1 1 calc R . .
H05I H 0.5909 1.4073 0.6654 0.14 Uiso 1 1 calc R . .
C057 C 0.7187(3) 0.9055(3) 0.1538(3) 0.0510(12) Uani 1 1 d . . .
C5B C 0.8443(2) 1.2046(3) 0.5589(2) 0.0423(10) Uani 1 1 d . . .
H058 H 0.8482 1.262 0.577 0.051 Uiso 1 1 calc R . .
C059 C 0.9831(3) 1.3638(4) 0.3488(4) 0.0788(18) Uani 1 1 d . . .
H059 H 1.0142 1.3992 0.3196 0.095 Uiso 1 1 calc R . .
C060 C 0.8607(3) 0.9761(3) 0.1004(3) 0.0557(13) Uani 1 1 d . . .
H060 H 0.9096 0.9995 0.082 0.067 Uiso 1 1 calc R . .
C061 C 0.8977(3) 1.2452(3) 0.3630(3) 0.0587(13) Uani 1 1 d . . .
C062 C 0.6816(3) 1.2864(3) 0.6137(2) 0.0451(11) Uani 1 1 d . . .
C063 C 0.9774(3) 1.3803(3) 0.4208(4) 0.0705(16) Uani 1 1 d . . .
H063 H 1.0063 1.4253 0.4406 0.085 Uiso 1 1 calc R . .
O1A O 0.64283(17) 0.79670(17) -0.15700(14) 0.0452(7) Uani 1 1 d . . .
H1A1 H 0.6897 0.7888 -0.1737 0.068 Uiso 1 1 calc R . .
O1B O 0.79497(18) 1.16094(19) 0.67574(14) 0.0542(8) Uani 1 1 d . . .
H1B1 H 0.8012 1.2096 0.6886 0.081 Uiso 1 1 calc R . .
O2A O 0.7983(2) 0.7264(2) -0.1491(2) 0.0750(10) Uani 1 1 d . . .
O2B O 0.6626(2) 1.0252(2) 0.6679(2) 0.0799(11) Uani 1 1 d . . .
O3A O 0.81538(17) 0.62208(17) -0.07266(16) 0.0532(8) Uani 1 1 d . . .
O3B O 0.78233(17) 0.95517(18) 0.66746(16) 0.0531(8) Uani 1 1 d . . .
O4A O 0.4944(2) 0.6203(2) 0.12151(18) 0.0741(10) Uani 1 1 d . . .
O4B O 0.6313(3) 1.0044(2) 0.3955(2) 0.0922(12) Uani 1 1 d . . .
O5A O 0.6297(2) 0.58856(19) 0.13140(16) 0.0620(9) Uani 1 1 d . . .
O5B O 0.5912(2) 1.1373(2) 0.38554(17) 0.0716(9) Uani 1 1 d . . .
O6A O 0.45047(16) 0.7171(2) 0.01983(17) 0.0577(8) Uani 1 1 d . . .
H6A H 0.4424 0.6847 0.0532 0.087 Uiso 1 1 calc R . .
O6B O 0.9540(2) 1.1047(3) 0.5353(3) 0.0977(14) Uani 1 1 d . . .
O7A O 0.5847(2) 0.95001(19) -0.02249(19) 0.0648(9) Uani 1 1 d . . .
O7B O 0.9713(2) 1.1961(3) 0.6227(2) 0.0976(13) Uani 1 1 d . . .
O8A O 0.6862(2) 0.97213(17) -0.10096(17) 0.0590(8) Uani 1 1 d . . .
O8B O 0.7297(2) 1.3210(2) 0.6532(2) 0.0772(11) Uani 1 1 d . . .
O9A O 0.51147(17) 0.6547(2) -0.14720(16) 0.0586(8) Uani 1 1 d . . .
O9B O 0.6114(2) 1.32172(18) 0.59099(18) 0.0665(9) Uani 1 1 d . . .
O10A O 0.44313(16) 0.77676(17) -0.15332(15) 0.0487(7) Uani 1 1 d . . .
O10B O 0.7300(2) 0.96550(18) 0.4978(2) 0.0681(9) Uani 1 1 d . . .
H10B H 0.7006 0.9563 0.4626 0.102 Uiso 1 1 calc R . .
Br1A Br 0.62311(3) 0.85573(4) 0.19647(3) 0.0867(2) Uani 1 1 d . . .
Br1B Br 0.84442(4) 1.15441(4) 0.31741(3) 0.0904(2) Uani 1 1 d . . .
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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
O8A C1 H1A 109.5 . . ?
O8A C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O8A C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O5B C2 H2A 109.5 . . ?
O5B C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
O5B C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O7B C3 H3A 109.5 . . ?
O7B C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
O7B C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C012 C2A C027 107.0(3) . . ?
C012 C2A C1A 113.9(3) . . ?
C027 C2A C1A 110.4(3) . . ?
C012 C2A H001 108.4 . . ?
C027 C2A H001 108.4 . . ?
C1A C2A H001 108.4 . . ?
C012 C009 C055 118.7(4) . . ?
C012 C009 C3A 121.4(4) . . ?
C055 C009 C3A 119.6(4) . . ?
C009 C012 O6A 124.2(4) . . ?
C009 C012 C2A 123.9(3) . . ?
O6A C012 C2A 111.9(3) . . ?
C3A C013 C6A 111.3(3) . . ?
C3A C013 H01A 109.4 . . ?
C6A C013 H01A 109.4 . . ?
C3A C013 H01B 109.4 . . ?
C6A C013 H01B 109.4 . . ?
H01A C013 H01B 108 . . ?
C036 C6A C5A 114.9(3) . . ?
C036 C6A C013 109.7(3) . . ?
C5A C6A C013 109.7(3) . . ?
C036 C6A H015 107.4 . . ?
C5A C6A H015 107.4 . . ?
C013 C6A H015 107.4 . . ?
O2B C016 O3B 123.5(4) . . ?
O2B C016 C2B 125.7(4) . . ?
O3B C016 C2B 110.8(4) . . ?
C3B C018 C6B 111.2(3) . . ?
C3B C018 H01C 109.4 . . ?
C6B C018 H01C 109.4 . . ?
C3B C018 H01D 109.4 . . ?
C6B C018 H01D 109.4 . . ?
H01C C018 H01D 108 . . ?
C032 C6B C5B 115.2(3) . . ?
C032 C6B C018 108.8(3) . . ?
C5B C6B C018 110.6(3) . . ?
C032 C6B H019 107.3 . . ?
C5B C6B H019 107.3 . . ?
C018 C6B H019 107.3 . . ?
C023 C4A C3A 114.4(3) . . ?
C023 C4A C1A 113.6(3) . . ?
C3A C4A C1A 109.1(3) . . ?
C023 C4A H021 106.4 . . ?
C3A C4A H021 106.4 . . ?
C1A C4A H021 106.4 . . ?
O1A C1A C4A 113.1(3) . . ?
O1A C1A C2A 104.3(3) . . ?
C4A C1A C2A 108.4(3) . . ?
O1A C1A C5A 108.7(3) . . ?
C4A C1A C5A 109.0(3) . . ?
C2A C1A C5A 113.3(3) . . ?
O2A C023 O3A 123.3(4) . . ?
O2A C023 C4A 124.8(4) . . ?
O3A C023 C4A 111.9(4) . . ?
C028 C5A C6A 110.1(3) . . ?
C028 C5A C1A 110.1(3) . . ?
C6A C5A C1A 113.5(3) . . ?
C028 C5A H024 107.6 . . ?
C6A C5A H024 107.6 . . ?
C1A C5A H024 107.6 . . ?
O9A C027 O10A 124.8(4) . . ?
O9A C027 C2A 124.4(4) . . ?
O10A C027 C2A 110.8(4) . . ?
O7A C028 O8A 123.9(4) . . ?
O7A C028 C5A 123.8(4) . . ?
O8A C028 C5A 112.3(4) . . ?
C032 C031 C063 120.7(5) . . ?
C032 C031 H031 119.6 . . ?
C063 C031 H031 119.6 . . ?
C031 C032 C061 117.2(4) . . ?
C031 C032 C6B 122.0(4) . . ?
C061 C032 C6B 120.6(4) . . ?
C042 C3B C4B 110.5(3) . . ?
C042 C3B C018 111.3(3) . . ?
C4B C3B C018 108.9(3) . . ?
C042 C3B H034 108.7 . . ?
C4B C3B H034 108.7 . . ?
C018 C3B H034 108.7 . . ?
O5A C035 H03A 109.5 . . ?
O5A C035 H03B 109.5 . . ?
H03A C035 H03B 109.5 . . ?
O5A C035 H03C 109.5 . . ?
H03A C035 H03C 109.5 . . ?
H03B C035 H03C 109.5 . . ?
C047 C036 C057 116.2(4) . . ?
C047 C036 C6A 121.9(4) . . ?
C057 C036 C6A 121.6(4) . . ?
C049 C038 C060 120.1(5) . . ?
C049 C038 H038 120 . . ?
C060 C038 H038 120 . . ?
C044 C2B C016 107.8(3) . . ?
C044 C2B C1B 113.7(3) . . ?
C016 C2B C1B 111.4(3) . . ?
C044 C2B H039 107.9 . . ?
C016 C2B H039 107.9 . . ?
C1B C2B H039 107.9 . . ?
O4B C040 O5B 122.5(4) . . ?
O4B C040 C042 124.5(5) . . ?
O5B C040 C042 113.0(4) . . ?
C044 C042 C040 118.3(4) . . ?
C044 C042 C3B 120.2(4) . . ?
C040 C042 C3B 121.1(4) . . ?
C062 C4B C3B 112.1(3) . . ?
C062 C4B C1B 113.1(3) . . ?
C3B C4B C1B 108.9(3) . . ?
C062 C4B H043 107.5 . . ?
C3B C4B H043 107.5 . . ?
C1B C4B H043 107.5 . . ?
C042 C044 O10B 124.2(4) . . ?
C042 C044 C2B 124.6(4) . . ?
O10B C044 C2B 111.3(4) . . ?
O6B C045 O7B 124.2(6) . . ?
O6B C045 C5B 123.3(5) . . ?
O7B C045 C5B 112.5(6) . . ?
C061 C046 C059 118.8(5) . . ?
C061 C046 H046 120.6 . . ?
C059 C046 H046 120.6 . . ?
C060 C047 C036 121.6(4) . . ?
C060 C047 H047 119.2 . . ?
C036 C047 H047 119.2 . . ?
O10A C048 H04A 109.5 . . ?
O10A C048 H04B 109.5 . . ?
H04A C048 H04B 109.5 . . ?
O10A C048 H04C 109.5 . . ?
H04A C048 H04C 109.5 . . ?
H04B C048 H04C 109.5 . . ?
C038 C049 C057 118.9(5) . . ?
C038 C049 H049 120.6 . . ?
C057 C049 H049 120.6 . . ?
O3B C050 H05A 109.5 . . ?
O3B C050 H05B 109.5 . . ?
H05A C050 H05B 109.5 . . ?
O3B C050 H05C 109.5 . . ?
H05A C050 H05C 109.5 . . ?
H05B C050 H05C 109.5 . . ?
O1B C1B C4B 112.1(3) . . ?
O1B C1B C2B 104.2(3) . . ?
C4B C1B C2B 107.6(3) . . ?
O1B C1B C5B 109.9(3) . . ?
C4B C1B C5B 110.4(3) . . ?
C2B C1B C5B 112.6(3) . . ?
O3A C053 H05D 109.5 . . ?
O3A C053 H05E 109.5 . . ?
H05D C053 H05E 109.5 . . ?
O3A C053 H05F 109.5 . . ?
H05D C053 H05F 109.5 . . ?
H05E C053 H05F 109.5 . . ?
C4A C3A C009 109.4(3) . . ?
C4A C3A C013 109.8(3) . . ?
C009 C3A C013 110.2(3) . . ?
C4A C3A H054 109.1 . . ?
C009 C3A H054 109.1 . . ?
C013 C3A H054 109.1 . . ?
O4A C055 O5A 122.4(4) . . ?
O4A C055 C009 123.8(4) . . ?
O5A C055 C009 113.8(4) . . ?
O9B C056 H05G 109.5 . . ?
O9B C056 H05H 109.5 . . ?
H05G C056 H05H 109.5 . . ?
O9B C056 H05I 109.5 . . ?
H05G C056 H05I 109.5 . . ?
H05H C056 H05I 109.5 . . ?
C049 C057 C036 122.5(4) . . ?
C049 C057 Br1A 116.8(4) . . ?
C036 C057 Br1A 120.6(3) . . ?
C6B C5B C045 109.4(4) . . ?
C6B C5B C1B 113.3(3) . . ?
C045 C5B C1B 110.9(3) . . ?
C6B C5B H058 107.7 . . ?
C045 C5B H058 107.7 . . ?
C1B C5B H058 107.7 . . ?
C046 C059 C063 120.9(5) . . ?
C046 C059 H059 119.6 . . ?
C063 C059 H059 119.6 . . ?
C038 C060 C047 120.6(5) . . ?
C038 C060 H060 119.7 . . ?
C047 C060 H060 119.7 . . ?
C046 C061 C032 122.9(5) . . ?
C046 C061 Br1B 115.6(4) . . ?
C032 C061 Br1B 121.5(3) . . ?
O8B C062 O9B 122.8(4) . . ?
O8B C062 C4B 125.8(4) . . ?
O9B C062 C4B 111.3(4) . . ?
C059 C063 C031 119.4(5) . . ?
C059 C063 H063 120.3 . . ?
C031 C063 H063 120.3 . . ?
C1A O1A H1A1 109.5 . . ?
C1B O1B H1B1 109.5 . . ?
C023 O3A C053 117.7(4) . . ?
C016 O3B C050 115.9(3) . . ?
C055 O5A C035 117.4(4) . . ?
C040 O5B C2 116.0(4) . . ?
C012 O6A H6A 109.5 . . ?
C045 O7B C3 108.0(6) . . ?
C028 O8A C1 115.6(4) . . ?
C062 O9B C056 118.0(4) . . ?
C027 O10A C048 115.9(3) . . ?
C044 O10B H10B 109.5 . . ?
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
C1 O8A 1.449(5) . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C2 O5B 1.443(6) . ?
C2 H2A 0.96 . ?
C2 H2B 0.96 . ?
C2 H2C 0.96 . ?
C3 O7B 1.510(7) . ?
C3 H3A 0.96 . ?
C3 H3B 0.96 . ?
C3 H3C 0.96 . ?
C2A C012 1.495(5) . ?
C2A C027 1.526(6) . ?
C2A C1A 1.548(5) . ?
C2A H001 0.98 . ?
C009 C012 1.325(5) . ?
C009 C055 1.458(6) . ?
C009 C3A 1.520(5) . ?
C012 O6A 1.342(4) . ?
C013 C3A 1.531(5) . ?
C013 C6A 1.540(5) . ?
C013 H01A 0.97 . ?
C013 H01B 0.97 . ?
C6A C036 1.503(5) . ?
C6A C5A 1.524(5) . ?
C6A H015 0.98 . ?
C016 O2B 1.176(5) . ?
C016 O3B 1.334(5) . ?
C016 C2B 1.514(6) . ?
C018 C3B 1.523(5) . ?
C018 C6B 1.533(5) . ?
C018 H01C 0.97 . ?
C018 H01D 0.97 . ?
C6B C032 1.511(5) . ?
C6B C5B 1.525(5) . ?
C6B H019 0.98 . ?
C4A C023 1.513(6) . ?
C4A C3A 1.520(5) . ?
C4A C1A 1.529(5) . ?
C4A H021 0.98 . ?
C1A O1A 1.413(4) . ?
C1A C5A 1.558(5) . ?
C023 O2A 1.202(5) . ?
C023 O3A 1.310(5) . ?
C5A C028 1.518(6) . ?
C5A H024 0.98 . ?
C027 O9A 1.191(5) . ?
C027 O10A 1.331(5) . ?
C028 O7A 1.191(5) . ?
C028 O8A 1.315(5) . ?
C031 C032 1.377(6) . ?
C031 C063 1.396(7) . ?
C031 H031 0.93 . ?
C032 C061 1.390(6) . ?
C3B C042 1.494(5) . ?
C3B C4B 1.525(5) . ?
C3B H034 0.98 . ?
C035 O5A 1.448(5) . ?
C035 H03A 0.96 . ?
C035 H03B 0.96 . ?
C035 H03C 0.96 . ?
C036 C047 1.381(5) . ?
C036 C057 1.392(6) . ?
C038 C049 1.367(7) . ?
C038 C060 1.361(7) . ?
C038 H038 0.93 . ?
C2B C044 1.490(6) . ?
C2B C1B 1.552(6) . ?
C2B H039 0.98 . ?
C040 O4B 1.209(5) . ?
C040 O5B 1.326(5) . ?
C040 C042 1.450(6) . ?
C042 C044 1.337(6) . ?
C4B C062 1.507(6) . ?
C4B C1B 1.527(5) . ?
C4B H043 0.98 . ?
C044 O10B 1.347(5) . ?
C045 O6B 1.200(7) . ?
C045 O7B 1.298(7) . ?
C045 C5B 1.529(7) . ?
C046 C061 1.360(7) . ?
C046 C059 1.366(8) . ?
C046 H046 0.93 . ?
C047 C060 1.376(6) . ?
C047 H047 0.93 . ?
C048 O10A 1.437(5) . ?
C048 H04A 0.96 . ?
C048 H04B 0.96 . ?
C048 H04C 0.96 . ?
C049 C057 1.385(6) . ?
C049 H049 0.93 . ?
C050 O3B 1.449(5) . ?
C050 H05A 0.96 . ?
C050 H05B 0.96 . ?
C050 H05C 0.96 . ?
C1B O1B 1.410(5) . ?
C1B C5B 1.548(5) . ?
C053 O3A 1.439(5) . ?
C053 H05D 0.96 . ?
C053 H05E 0.96 . ?
C053 H05F 0.96 . ?
C3A H054 0.98 . ?
C055 O4A 1.220(5) . ?
C055 O5A 1.316(5) . ?
C056 O9B 1.437(5) . ?
C056 H05G 0.96 . ?
C056 H05H 0.96 . ?
C056 H05I 0.96 . ?
C057 Br1A 1.895(5) . ?
C5B H058 0.98 . ?
C059 C063 1.374(7) . ?
C059 H059 0.93 . ?
C060 H060 0.93 . ?
C061 Br1B 1.884(5) . ?
C062 O8B 1.199(5) . ?
C062 O9B 1.323(5) . ?
C063 H063 0.93 . ?
O1A H1A1 0.82 . ?
O1B H1B1 0.82 . ?
O6A H6A 0.82 . ?
O10B H10B 0.82 . ?
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
C055 C009 C012 O6A -4.1(6) . . . . ?
C3A C009 C012 O6A -177.6(3) . . . . ?
C055 C009 C012 C2A 177.2(4) . . . . ?
C3A C009 C012 C2A 3.7(6) . . . . ?
C027 C2A C012 C009 112.8(4) . . . . ?
C1A C2A C012 C009 -9.5(5) . . . . ?
C027 C2A C012 O6A -66.0(4) . . . . ?
C1A C2A C012 O6A 171.6(3) . . . . ?
C3A C013 C6A C036 178.9(3) . . . . ?
C3A C013 C6A C5A -54.0(4) . . . . ?
C3B C018 C6B C032 178.1(3) . . . . ?
C3B C018 C6B C5B -54.4(4) . . . . ?
C023 C4A C1A O1A 51.5(4) . . . . ?
C3A C4A C1A O1A -179.6(3) . . . . ?
C023 C4A C1A C2A 166.7(3) . . . . ?
C3A C4A C1A C2A -64.4(4) . . . . ?
C023 C4A C1A C5A -69.6(4) . . . . ?
C3A C4A C1A C5A 59.3(4) . . . . ?
C012 C2A C1A O1A 159.8(3) . . . . ?
C027 C2A C1A O1A 39.3(4) . . . . ?
C012 C2A C1A C4A 39.0(4) . . . . ?
C027 C2A C1A C4A -81.5(4) . . . . ?
C012 C2A C1A C5A -82.1(4) . . . . ?
C027 C2A C1A C5A 157.4(3) . . . . ?
C3A C4A C023 O2A -145.9(4) . . . . ?
C1A C4A C023 O2A -19.7(6) . . . . ?
C3A C4A C023 O3A 35.7(5) . . . . ?
C1A C4A C023 O3A 161.9(3) . . . . ?
C036 C6A C5A C028 -59.5(4) . . . . ?
C013 C6A C5A C028 176.4(3) . . . . ?
C036 C6A C5A C1A 176.5(3) . . . . ?
C013 C6A C5A C1A 52.3(4) . . . . ?
O1A C1A C5A C028 56.6(4) . . . . ?
C4A C1A C5A C028 -179.7(3) . . . . ?
C2A C1A C5A C028 -58.9(4) . . . . ?
O1A C1A C5A C6A -179.4(3) . . . . ?
C4A C1A C5A C6A -55.6(4) . . . . ?
C2A C1A C5A C6A 65.2(4) . . . . ?
C012 C2A C027 O9A -59.9(5) . . . . ?
C1A C2A C027 O9A 64.7(5) . . . . ?
C012 C2A C027 O10A 118.1(4) . . . . ?
C1A C2A C027 O10A -117.4(4) . . . . ?
C6A C5A C028 O7A -44.1(5) . . . . ?
C1A C5A C028 O7A 81.9(5) . . . . ?
C6A C5A C028 O8A 136.1(3) . . . . ?
C1A C5A C028 O8A -97.9(4) . . . . ?
C063 C031 C032 C061 1.6(6) . . . . ?
C063 C031 C032 C6B -173.4(4) . . . . ?
C5B C6B C032 C031 -30.6(5) . . . . ?
C018 C6B C032 C031 94.3(4) . . . . ?
C5B C6B C032 C061 154.6(4) . . . . ?
C018 C6B C032 C061 -80.6(4) . . . . ?
C6B C018 C3B C042 -60.2(4) . . . . ?
C6B C018 C3B C4B 61.7(4) . . . . ?
C5A C6A C036 C047 -37.9(5) . . . . ?
C013 C6A C036 C047 86.2(4) . . . . ?
C5A C6A C036 C057 148.2(4) . . . . ?
C013 C6A C036 C057 -87.7(4) . . . . ?
O2B C016 C2B C044 -64.8(6) . . . . ?
O3B C016 C2B C044 112.2(4) . . . . ?
O2B C016 C2B C1B 60.6(6) . . . . ?
O3B C016 C2B C1B -122.4(4) . . . . ?
O4B C040 C042 C044 5.1(7) . . . . ?
O5B C040 C042 C044 -174.7(4) . . . . ?
O4B C040 C042 C3B 178.0(5) . . . . ?
O5B C040 C042 C3B -1.7(6) . . . . ?
C4B C3B C042 C044 -28.8(5) . . . . ?
C018 C3B C042 C044 92.3(4) . . . . ?
C4B C3B C042 C040 158.4(4) . . . . ?
C018 C3B C042 C040 -80.5(5) . . . . ?
C042 C3B C4B C062 -175.2(3) . . . . ?
C018 C3B C4B C062 62.3(4) . . . . ?
C042 C3B C4B C1B 58.9(4) . . . . ?
C018 C3B C4B C1B -63.6(4) . . . . ?
C040 C042 C044 O10B -2.5(7) . . . . ?
C3B C042 C044 O10B -175.5(4) . . . . ?
C040 C042 C044 C2B 178.3(4) . . . . ?
C3B C042 C044 C2B 5.4(6) . . . . ?
C016 C2B C044 C042 112.5(5) . . . . ?
C1B C2B C044 C042 -11.5(6) . . . . ?
C016 C2B C044 O10B -66.8(4) . . . . ?
C1B C2B C044 O10B 169.2(3) . . . . ?
C057 C036 C047 C060 0.8(6) . . . . ?
C6A C036 C047 C060 -173.5(3) . . . . ?
C060 C038 C049 C057 0.0(7) . . . . ?
C062 C4B C1B O1B 56.2(4) . . . . ?
C3B C4B C1B O1B -178.4(3) . . . . ?
C062 C4B C1B C2B 170.2(3) . . . . ?
C3B C4B C1B C2B -64.4(4) . . . . ?
C062 C4B C1B C5B -66.6(4) . . . . ?
C3B C4B C1B C5B 58.7(4) . . . . ?
C044 C2B C1B O1B 159.4(3) . . . . ?
C016 C2B C1B O1B 37.3(4) . . . . ?
C044 C2B C1B C4B 40.2(4) . . . . ?
C016 C2B C1B C4B -81.8(4) . . . . ?
C044 C2B C1B C5B -81.6(4) . . . . ?
C016 C2B C1B C5B 156.4(3) . . . . ?
C023 C4A C3A C009 -173.2(3) . . . . ?
C1A C4A C3A C009 58.2(4) . . . . ?
C023 C4A C3A C013 65.7(4) . . . . ?
C1A C4A C3A C013 -62.8(4) . . . . ?
C012 C009 C3A C4A -28.1(5) . . . . ?
C055 C009 C3A C4A 158.6(3) . . . . ?
C012 C009 C3A C013 92.8(4) . . . . ?
C055 C009 C3A C013 -80.6(4) . . . . ?
C6A C013 C3A C4A 60.3(4) . . . . ?
C6A C013 C3A C009 -60.3(4) . . . . ?
C012 C009 C055 O4A 5.6(6) . . . . ?
C3A C009 C055 O4A 179.1(4) . . . . ?
C012 C009 C055 O5A -173.1(4) . . . . ?
C3A C009 C055 O5A 0.5(5) . . . . ?
C038 C049 C057 C036 -0.5(7) . . . . ?
C038 C049 C057 Br1A 177.7(3) . . . . ?
C047 C036 C057 C049 0.1(6) . . . . ?
C6A C036 C057 C049 174.4(4) . . . . ?
C047 C036 C057 Br1A -178.0(3) . . . . ?
C6A C036 C057 Br1A -3.8(5) . . . . ?
C032 C6B C5B C045 -61.8(5) . . . . ?
C018 C6B C5B C045 174.4(3) . . . . ?
C032 C6B C5B C1B 173.9(3) . . . . ?
C018 C6B C5B C1B 50.0(4) . . . . ?
O6B C045 C5B C6B -39.0(6) . . . . ?
O7B C045 C5B C6B 142.7(4) . . . . ?
O6B C045 C5B C1B 86.6(6) . . . . ?
O7B C045 C5B C1B -91.7(5) . . . . ?
O1B C1B C5B C6B -177.0(3) . . . . ?
C4B C1B C5B C6B -52.9(4) . . . . ?
C2B C1B C5B C6B 67.3(4) . . . . ?
O1B C1B C5B C045 59.5(5) . . . . ?
C4B C1B C5B C045 -176.4(4) . . . . ?
C2B C1B C5B C045 -56.2(5) . . . . ?
C061 C046 C059 C063 0.3(7) . . . . ?
C049 C038 C060 C047 0.9(7) . . . . ?
C036 C047 C060 C038 -1.3(6) . . . . ?
C059 C046 C061 C032 2.8(7) . . . . ?
C059 C046 C061 Br1B 179.2(4) . . . . ?
C031 C032 C061 C046 -3.8(6) . . . . ?
C6B C032 C061 C046 171.3(4) . . . . ?
C031 C032 C061 Br1B -179.9(3) . . . . ?
C6B C032 C061 Br1B -4.8(5) . . . . ?
C3B C4B C062 O8B -135.3(5) . . . . ?
C1B C4B C062 O8B -11.7(6) . . . . ?
C3B C4B C062 O9B 47.9(5) . . . . ?
C1B C4B C062 O9B 171.4(3) . . . . ?
C046 C059 C063 C031 -2.4(7) . . . . ?
C032 C031 C063 C059 1.4(6) . . . . ?
O2A C023 O3A C053 -4.1(6) . . . . ?
C4A C023 O3A C053 174.3(4) . . . . ?
O2B C016 O3B C050 3.1(7) . . . . ?
C2B C016 O3B C050 -174.0(4) . . . . ?
O4A C055 O5A C035 -1.8(6) . . . . ?
C009 C055 O5A C035 176.9(4) . . . . ?
O4B C040 O5B C2 -0.6(7) . . . . ?
C042 C040 O5B C2 179.1(5) . . . . ?
O6B C045 O7B C3 -1.5(7) . . . . ?
C5B C045 O7B C3 176.8(4) . . . . ?
O7A C028 O8A C1 -4.8(6) . . . . ?
C5A C028 O8A C1 175.0(4) . . . . ?
O8B C062 O9B C056 1.1(7) . . . . ?
C4B C062 O9B C056 178.1(4) . . . . ?
O9A C027 O10A C048 3.1(6) . . . . ?
C2A C027 O10A C048 -174.8(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 29330431
2 PubChem 139180486
