#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017085.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_2017085
loop_
_publ_author_name
'Beck, Tobias'
'Herbst-Irmer, Regine'
'Sheldrick, George M.'
_publ_section_title
;
 5-Amino-2,4,6-tribromoisophthalic acid: the MAD triangle for
 experimental phasing
;
_journal_coeditor_code           EG3012
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o237
_journal_page_last               o239
_journal_paper_doi               10.1107/S0108270109013195
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C8 H4 Br3 N O4'
_chemical_formula_moiety         'C8 H4 Br3 N O4'
_chemical_formula_sum            'C8 H4 Br3 N O4'
_chemical_formula_weight         417.85
_chemical_name_systematic
;
5-Amino-2,4,6-tribromoisophthalic acid
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.69(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   16.728(2)
_cell_length_b                   11.449(2)
_cell_length_c                   23.649(3)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.361
_cell_measurement_theta_min      2.65
_cell_volume                     4464.6(12)
_computing_cell_refinement       'SAINT (Bruker 2007)'
_computing_data_collection       'APEX2 (Bruker 2007)'
_computing_data_reduction        'SAINT (Bruker 2007)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and PyMOL (DeLano, 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.602
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker SMART 6000'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'INCOATEC multilayer optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            97602
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         73.98
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    13.443
_exptl_absorpt_correction_T_max  0.5529
_exptl_absorpt_correction_T_min  0.3466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(TWINABS; Sheldrick 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.487
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.640
_refine_diff_density_min         -0.546
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         8717
_refine_ls_number_restraints     106
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0258
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0207P)²+12.7819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                8413
_reflns_number_total             8717
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            eg3012.cif
_cod_data_source_block           B3C
_cod_original_cell_volume        4464.6(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017085
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.76858(3) 1.05153(4) 0.838008(17) 0.01823(9) Uani d D 1 . .
Br Br2 0.90200(3) 0.77141(4) 1.029830(19) 0.02257(10) Uani d D 1 . .
Br Br3 0.56589(3) 0.86912(4) 0.98543(2) 0.02519(10) Uani d D 1 . .
Br Br4 0.64571(3) 0.60368(4) 0.904198(19) 0.02267(10) Uani d D 1 . .
Br Br5 0.56822(3) 0.22804(4) 0.749209(18) 0.01939(9) Uani d D 1 . .
Br Br6 0.89510(3) 0.37978(4) 0.809858(19) 0.02070(9) Uani d D 1 . .
Br Br7 0.30715(3) 0.88711(4) 0.893986(19) 0.02120(10) Uani d D 1 . .
Br Br8 0.31319(3) 1.28060(4) 0.749327(18) 0.02129(10) Uani d D 1 . .
Br Br9 0.01216(3) 1.10091(4) 0.79249(2) 0.02637(10) Uani d D 1 . .
Br Br10 0.15775(3) 0.44910(4) 0.841601(17) 0.01817(9) Uani d D 1 . .
Br Br11 0.11675(3) 0.75056(4) 1.026098(19) 0.02112(10) Uani d D 1 . .
Br Br12 0.43125(3) 0.63902(4) 0.98528(2) 0.02353(10) Uani d D 1 . .
C C1 0.6798(3) 0.9498(3) 0.91806(17) 0.0167(8) Uani d D 1 . .
C C2 0.7560(3) 0.9621(3) 0.90358(17) 0.0160(8) Uani d D 1 . .
C C3 0.8230(3) 0.9105(3) 0.93721(17) 0.0166(8) Uani d D 1 . .
C C4 0.8123(2) 0.8504(3) 0.98608(17) 0.0155(8) Uani d D 1 . .
C C5 0.7365(3) 0.8375(3) 1.00379(17) 0.0179(8) Uani d D 1 . .
C C6 0.6713(2) 0.8890(3) 0.96729(17) 0.0178(8) Uani d D 1 . .
C C7 0.6050(2) 1.0021(4) 0.88183(18) 0.0183(8) Uani d D 1 . .
O O8 0.57574(19) 0.9368(3) 0.83757(13) 0.0238(7) Uani d D 1 . .
H H8 0.536(2) 0.963(5) 0.824(2) 0.036 Uiso d D 1 . .
O O9 0.57613(18) 1.0938(3) 0.89427(13) 0.0223(6) Uani d D 1 . .
C C10 0.9040(2) 0.9133(3) 0.91817(17) 0.0162(8) Uani d D 1 . .
O O11 0.92055(19) 0.8445(3) 0.88246(14) 0.0238(7) Uani d D 1 . .
O O12 0.95320(19) 0.9935(3) 0.94279(14) 0.0232(7) Uani d D 1 . .
H H12 0.994(2) 0.979(5) 0.935(2) 0.035 Uiso d D 1 . .
N N13 0.7277(2) 0.7801(4) 1.05272(17) 0.0241(8) Uani d D 1 . .
H H13 0.6770(16) 0.757(4) 1.051(2) 0.036 Uiso d D 1 . .
H H13A 0.769(2) 0.745(4) 1.073(2) 0.036 Uiso d D 1 . .
C C21 0.7600(3) 0.4797(3) 0.85018(16) 0.0162(8) Uani d D 1 . .
C C22 0.6789(3) 0.4883(3) 0.85471(16) 0.0160(8) Uani d D 1 . .
C C23 0.6225(2) 0.4136(3) 0.82545(16) 0.0153(8) Uani d D 1 . .
C C24 0.6476(2) 0.3303(3) 0.78926(16) 0.0153(8) Uani d D 1 . .
C C25 0.7280(3) 0.3201(3) 0.78067(16) 0.0159(8) Uani d D 1 . .
C C26 0.7833(2) 0.3956(3) 0.81371(17) 0.0157(8) Uani d D 1 . .
C C27 0.8232(2) 0.5593(4) 0.88267(17) 0.0166(8) Uani d D 1 . .
O O28 0.86495(18) 0.5320(3) 0.92774(12) 0.0219(6) Uani d D 1 . .
O O29 0.8266(2) 0.6583(3) 0.85552(14) 0.0260(7) Uani d D 1 . .
H H29 0.861(3) 0.693(5) 0.873(2) 0.039 Uiso d D 1 . .
C C30 0.5351(2) 0.4202(3) 0.83260(16) 0.0149(8) Uani d D 1 . .
O O31 0.51670(18) 0.3518(3) 0.87166(13) 0.0203(6) Uani d D 1 . .
H H31 0.4737(19) 0.355(5) 0.878(2) 0.031 Uiso d D 1 . .
O O32 0.48697(19) 0.4879(3) 0.80339(13) 0.0247(7) Uani d D 1 . .
N N33 0.7523(2) 0.2377(3) 0.74472(16) 0.0195(7) Uani d D 1 . .
H H33 0.8012(18) 0.253(5) 0.738(2) 0.029 Uiso d D 1 . .
H H33A 0.716(2) 0.200(4) 0.7204(18) 0.029 Uiso d D 1 . .
C C41 0.1668(3) 1.0069(4) 0.83694(17) 0.0184(8) Uani d D 1 . .
C C42 0.2508(3) 1.0023(4) 0.84464(17) 0.0177(8) Uani d D 1 . .
C C43 0.2945(2) 1.0834(3) 0.81878(16) 0.0149(8) Uani d D 1 . .
C C44 0.2523(3) 1.1710(3) 0.78541(16) 0.0178(8) Uani d D 1 . .
C C45 0.1678(3) 1.1811(3) 0.77678(16) 0.0173(8) Uani d D 1 . .
C C46 0.1274(2) 1.0955(4) 0.80361(16) 0.0166(8) Uani d D 1 . .
C C47 0.1197(2) 0.9208(4) 0.86638(18) 0.0186(8) Uani d D 1 . .
O O48 0.09844(19) 0.9431(3) 0.91146(13) 0.0256(7) Uani d D 1 . .
O O49 0.1056(2) 0.8220(3) 0.83753(14) 0.0252(7) Uani d D 1 . .
H H49 0.085(4) 0.780(4) 0.855(2) 0.038 Uiso d D 1 . .
C C50 0.3855(3) 1.0774(3) 0.82770(17) 0.0167(8) Uani d D 1 . .
O O51 0.42168(18) 1.0111(3) 0.80107(13) 0.0225(6) Uani d D 1 . .
O O52 0.41920(18) 1.1482(3) 0.86847(13) 0.0202(6) Uani d D 1 . .
H H52 0.4648(16) 1.141(5) 0.876(2) 0.030 Uiso d D 1 . .
N N53 0.1271(2) 1.2725(3) 0.74634(15) 0.0191(7) Uani d D 1 . .
H H53 0.0747(16) 1.258(4) 0.736(2) 0.029 Uiso d D 1 . .
H H53A 0.153(2) 1.314(4) 0.7235(18) 0.029 Uiso d D 1 . .
C C61 0.2851(3) 0.5531(3) 0.92061(17) 0.0154(8) Uani d D 1 . .
C C62 0.2014(3) 0.5432(3) 0.90586(16) 0.0159(8) Uani d D 1 . .
C C63 0.1511(2) 0.5998(3) 0.93785(16) 0.0147(8) Uani d D 1 . .
C C64 0.1848(2) 0.6649(3) 0.98473(17) 0.0162(8) Uani d D 1 . .
C C65 0.2690(3) 0.6774(3) 1.00245(17) 0.0168(8) Uani d D 1 . .
C C66 0.3172(2) 0.6195(3) 0.96801(17) 0.0164(8) Uani d D 1 . .
C C67 0.3418(2) 0.4961(3) 0.88611(18) 0.0164(8) Uani d D 1 . .
O O68 0.35356(19) 0.5548(3) 0.84175(13) 0.0227(6) Uani d D 1 . .
H H68 0.388(3) 0.531(5) 0.829(2) 0.034 Uiso d D 1 . .
O O69 0.37485(18) 0.4021(3) 0.90131(14) 0.0230(7) Uani d D 1 . .
C C70 0.0602(2) 0.5937(4) 0.91988(17) 0.0167(8) Uani d D 1 . .
O O71 0.02428(18) 0.6549(3) 0.88189(13) 0.0208(6) Uani d D 1 . .
O O72 0.02670(18) 0.5167(3) 0.94889(14) 0.0234(7) Uani d D 1 . .
H H72 -0.0190(16) 0.519(5) 0.939(2) 0.035 Uiso d D 1 . .
N N73 0.3012(2) 0.7405(3) 1.04913(16) 0.0225(8) Uani d D 1 . .
H H73 0.3514(17) 0.753(4) 1.047(2) 0.034 Uiso d D 1 . .
H H73A 0.270(3) 0.782(4) 1.067(2) 0.034 Uiso d D 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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 C1 C6 . . 119.2(4) ?
C2 C1 C7 . . 121.9(4) ?
C6 C1 C7 . . 118.9(4) ?
C1 C2 C3 . . 120.2(4) ?
C1 C2 Br1 . . 119.4(3) ?
C3 C2 Br1 . . 120.4(3) ?
C4 C3 C2 . . 118.9(4) ?
C4 C3 C10 . . 120.9(4) ?
C2 C3 C10 . . 120.1(4) ?
C3 C4 C5 . . 123.4(4) ?
C3 C4 Br2 . . 119.3(3) ?
C5 C4 Br2 . . 117.1(3) ?
N13 C5 C6 . . 122.9(4) ?
N13 C5 C4 . . 122.3(4) ?
C6 C5 C4 . . 114.7(4) ?
C1 C6 C5 . . 123.4(4) ?
C1 C6 Br3 . . 118.7(3) ?
C5 C6 Br3 . . 117.8(3) ?
O9 C7 O8 . . 125.3(4) ?
O9 C7 C1 . . 122.0(4) ?
O8 C7 C1 . . 112.8(4) ?
C7 O8 H8 . . 107(5) ?
O11 C10 O12 . . 124.4(4) ?
O11 C10 C3 . . 121.1(4) ?
O12 C10 C3 . . 114.5(3) ?
C10 O12 H12 . . 105(5) ?
C5 N13 H13 . . 111(3) ?
C5 N13 H13A . . 121(4) ?
H13 N13 H13A . . 123(4) ?
C22 C21 C26 . . 118.6(4) ?
C22 C21 C27 . . 122.1(4) ?
C26 C21 C27 . . 119.3(4) ?
C23 C22 C21 . . 121.1(4) ?
C23 C22 Br4 . . 119.7(3) ?
C21 C22 Br4 . . 119.2(3) ?
C22 C23 C24 . . 119.0(4) ?
C22 C23 C30 . . 120.8(4) ?
C24 C23 C30 . . 120.2(4) ?
C23 C24 C25 . . 122.9(4) ?
C23 C24 Br5 . . 118.1(3) ?
C25 C24 Br5 . . 119.0(3) ?
N33 C25 C24 . . 122.6(4) ?
N33 C25 C26 . . 122.0(4) ?
C24 C25 C26 . . 115.3(4) ?
C21 C26 C25 . . 123.0(4) ?
C21 C26 Br6 . . 118.5(3) ?
C25 C26 Br6 . . 118.5(3) ?
O28 C27 O29 . . 126.0(4) ?
O28 C27 C21 . . 123.0(4) ?
O29 C27 C21 . . 111.0(3) ?
C27 O29 H29 . . 107(5) ?
O32 C30 O31 . . 124.6(4) ?
O32 C30 C23 . . 121.5(4) ?
O31 C30 C23 . . 113.9(3) ?
C30 O31 H31 . . 117(4) ?
C25 N33 H33 . . 111(3) ?
C25 N33 H33A . . 120(3) ?
H33 N33 H33A . . 122(3) ?
C46 C41 C42 . . 118.5(4) ?
C46 C41 C47 . . 120.6(4) ?
C42 C41 C47 . . 120.8(4) ?
C43 C42 C41 . . 121.0(4) ?
C43 C42 Br7 . . 119.4(3) ?
C41 C42 Br7 . . 119.5(3) ?
C42 C43 C44 . . 118.5(4) ?
C42 C43 C50 . . 120.3(4) ?
C44 C43 C50 . . 121.2(4) ?
C43 C44 C45 . . 123.1(4) ?
C43 C44 Br8 . . 118.0(3) ?
C45 C44 Br8 . . 118.9(3) ?
N53 C45 C44 . . 122.4(4) ?
N53 C45 C46 . . 122.2(4) ?
C44 C45 C46 . . 115.4(4) ?
C41 C46 C45 . . 123.5(4) ?
C41 C46 Br9 . . 118.5(3) ?
C45 C46 Br9 . . 118.0(3) ?
O48 C47 O49 . . 125.7(4) ?
O48 C47 C41 . . 121.7(4) ?
O49 C47 C41 . . 112.6(4) ?
C47 O49 H49 . . 108(5) ?
O51 C50 O52 . . 125.3(4) ?
O51 C50 C43 . . 122.6(4) ?
O52 C50 C43 . . 112.0(4) ?
C50 O52 H52 . . 113(4) ?
C45 N53 H53 . . 112(3) ?
C45 N53 H53A . . 118(3) ?
H53 N53 H53A . . 120(3) ?
C66 C61 C62 . . 119.0(4) ?
C66 C61 C67 . . 119.0(4) ?
C62 C61 C67 . . 122.0(4) ?
C63 C62 C61 . . 120.2(4) ?
C63 C62 Br10 . . 121.0(3) ?
C61 C62 Br10 . . 118.8(3) ?
C64 C63 C62 . . 119.4(4) ?
C64 C63 C70 . . 120.5(4) ?
C62 C63 C70 . . 120.0(4) ?
C63 C64 C65 . . 123.3(4) ?
C63 C64 Br11 . . 119.8(3) ?
C65 C64 Br11 . . 116.9(3) ?
N73 C65 C66 . . 122.4(4) ?
N73 C65 C64 . . 122.5(4) ?
C66 C65 C64 . . 115.0(4) ?
C61 C66 C65 . . 123.0(4) ?
C61 C66 Br12 . . 118.5(3) ?
C65 C66 Br12 . . 118.4(3) ?
O69 C67 O68 . . 124.7(4) ?
O69 C67 C61 . . 120.9(4) ?
O68 C67 C61 . . 114.4(3) ?
C67 O68 H68 . . 112(5) ?
O71 C70 O72 . . 125.3(4) ?
O71 C70 C63 . . 122.0(4) ?
O72 C70 C63 . . 112.7(3) ?
C70 O72 H72 . . 109(5) ?
C65 N73 H73 . . 107(4) ?
C65 N73 H73A . . 120(4) ?
H73 N73 H73A . . 128(4) ?
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 C2 . 1.899(4) ?
Br2 C4 . 1.902(4) ?
Br3 C6 . 1.898(4) ?
Br4 C22 . 1.908(4) ?
Br5 C24 . 1.899(4) ?
Br6 C26 . 1.897(4) ?
Br7 C42 . 1.903(4) ?
Br8 C44 . 1.906(4) ?
Br9 C46 . 1.903(4) ?
Br10 C62 . 1.905(4) ?
Br11 C64 . 1.895(4) ?
Br12 C66 . 1.895(4) ?
C1 C2 . 1.383(6) ?
C1 C6 . 1.384(6) ?
C1 C7 . 1.516(6) ?
C2 C3 . 1.392(6) ?
C3 C4 . 1.382(6) ?
C3 C10 . 1.499(6) ?
C4 C5 . 1.408(6) ?
C5 N13 . 1.360(6) ?
C5 C6 . 1.401(6) ?
C7 O9 . 1.212(5) yes
C7 O8 . 1.312(5) yes
O8 H8 . 0.75(3) ?
C10 O11 . 1.219(5) yes
C10 O12 . 1.303(5) yes
O12 H12 . 0.76(3) ?
N13 H13 . 0.88(2) ?
N13 H13A . 0.87(2) ?
C21 C22 . 1.382(6) ?
C21 C26 . 1.391(6) ?
C21 C27 . 1.505(6) ?
C22 C23 . 1.371(6) ?
C23 C24 . 1.393(6) ?
C23 C30 . 1.502(5) ?
C24 C25 . 1.399(6) ?
C25 N33 . 1.377(5) ?
C25 C26 . 1.403(6) ?
C27 O28 . 1.213(5) yes
C27 O29 . 1.309(5) yes
O29 H29 . 0.76(3) ?
C30 O32 . 1.240(5) yes
C30 O31 . 1.288(5) yes
O31 H31 . 0.76(3) ?
N33 H33 . 0.88(2) ?
N33 H33A . 0.88(2) ?
C41 C46 . 1.382(6) ?
C41 C42 . 1.387(6) ?
C41 C47 . 1.504(6) ?
C42 C43 . 1.387(6) ?
C43 C44 . 1.393(6) ?
C43 C50 . 1.502(6) ?
C44 C45 . 1.399(6) ?
C45 N53 . 1.383(5) ?
C45 C46 . 1.401(6) ?
C47 O48 . 1.207(5) yes
C47 O49 . 1.321(5) yes
O49 H49 . 0.75(3) ?
C50 O51 . 1.212(5) yes
C50 O52 . 1.312(5) yes
O52 H52 . 0.76(3) ?
N53 H53 . 0.88(2) ?
N53 H53A . 0.88(2) ?
C61 C66 . 1.386(6) ?
C61 C62 . 1.390(6) ?
C61 C67 . 1.500(6) ?
C62 C63 . 1.383(6) ?
C63 C64 . 1.375(6) ?
C63 C70 . 1.511(5) ?
C64 C65 . 1.407(6) ?
C65 N73 . 1.353(5) ?
C65 C66 . 1.405(6) ?
C67 O69 . 1.236(5) yes
C67 O68 . 1.289(5) yes
O68 H68 . 0.75(3) ?
C70 O71 . 1.215(5) yes
C70 O72 . 1.300(5) yes
O72 H72 . 0.76(3) ?
N73 H73 . 0.86(2) ?
N73 H73A . 0.86(2) ?
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
O8 H8 O51 . 0.75(3) 1.97(3) 2.713(4) 167(6)
O12 H12 O48 1_655 0.76(3) 1.96(3) 2.719(4) 177(6)
O52 H52 O9 . 0.76(3) 1.92(3) 2.667(4) 170(6)
O49 H49 O71 . 0.75(3) 1.93(3) 2.664(4) 165(7)
O31 H31 O69 . 0.76(3) 1.91(3) 2.649(4) 165(6)
O68 H68 O32 . 0.75(3) 1.91(3) 2.659(4) 171(6)
O72 H72 O28 1_455 0.76(3) 1.92(3) 2.673(4) 171(6)
O29 H29 O11 . 0.76(3) 1.99(4) 2.662(4) 147(6)
N33 H33A O68 2_646 0.88(2) 2.39(3) 3.237(5) 164(5)
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
C6 C1 C2 C3 . . . . 2.1(6) ?
C7 C1 C2 C3 . . . . -178.5(4) ?
C6 C1 C2 Br1 . . . . -177.1(3) ?
C7 C1 C2 Br1 . . . . 2.3(5) ?
C1 C2 C3 C4 . . . . -2.1(5) ?
Br1 C2 C3 C4 . . . . 177.1(3) ?
C1 C2 C3 C10 . . . . 173.6(4) ?
Br1 C2 C3 C10 . . . . -7.2(5) ?
C2 C3 C4 C5 . . . . 0.5(6) ?
C10 C3 C4 C5 . . . . -175.2(4) ?
C2 C3 C4 Br2 . . . . 176.2(3) ?
C10 C3 C4 Br2 . . . . 0.5(5) ?
C3 C4 C5 N13 . . . . -178.6(4) ?
Br2 C4 C5 N13 . . . . 5.6(5) ?
C3 C4 C5 C6 . . . . 1.0(5) ?
Br2 C4 C5 C6 . . . . -174.7(3) ?
C2 C1 C6 C5 . . . . -0.4(6) ?
C7 C1 C6 C5 . . . . -179.9(4) ?
C2 C1 C6 Br3 . . . . -178.2(3) ?
C7 C1 C6 Br3 . . . . 2.3(5) ?
N13 C5 C6 C1 . . . . 178.6(4) ?
C4 C5 C6 C1 . . . . -1.1(5) ?
N13 C5 C6 Br3 . . . . -3.6(5) ?
C4 C5 C6 Br3 . . . . 176.7(3) ?
C2 C1 C7 O9 . . . . -99.1(5) ?
C6 C1 C7 O9 . . . . 80.3(5) ?
C2 C1 C7 O8 . . . . 82.0(5) ?
C6 C1 C7 O8 . . . . -98.6(4) ?
C4 C3 C10 O11 . . . . 95.5(5) ?
C2 C3 C10 O11 . . . . -80.2(5) ?
C4 C3 C10 O12 . . . . -84.5(5) ?
C2 C3 C10 O12 . . . . 99.8(4) ?
C26 C21 C22 C23 . . . . 2.0(6) ?
C27 C21 C22 C23 . . . . -178.9(4) ?
C26 C21 C22 Br4 . . . . -179.7(3) ?
C27 C21 C22 Br4 . . . . -0.6(5) ?
C21 C22 C23 C24 . . . . -2.0(5) ?
Br4 C22 C23 C24 . . . . 179.7(3) ?
C21 C22 C23 C30 . . . . 177.3(4) ?
Br4 C22 C23 C30 . . . . -1.0(5) ?
C22 C23 C24 C25 . . . . -0.9(5) ?
C30 C23 C24 C25 . . . . 179.8(4) ?
C22 C23 C24 Br5 . . . . -180.0(3) ?
C30 C23 C24 Br5 . . . . 0.7(5) ?
C23 C24 C25 N33 . . . . -179.9(4) ?
Br5 C24 C25 N33 . . . . -0.8(5) ?
C23 C24 C25 C26 . . . . 3.5(5) ?
Br5 C24 C25 C26 . . . . -177.4(3) ?
C22 C21 C26 C25 . . . . 0.9(6) ?
C27 C21 C26 C25 . . . . -178.2(4) ?
C22 C21 C26 Br6 . . . . -177.6(3) ?
C27 C21 C26 Br6 . . . . 3.4(5) ?
N33 C25 C26 C21 . . . . 179.8(4) ?
C24 C25 C26 C21 . . . . -3.5(5) ?
N33 C25 C26 Br6 . . . . -1.7(5) ?
C24 C25 C26 Br6 . . . . 174.9(3) ?
C22 C21 C27 O28 . . . . 97.1(5) ?
C26 C21 C27 O28 . . . . -83.8(5) ?
C22 C21 C27 O29 . . . . -83.4(5) ?
C26 C21 C27 O29 . . . . 95.7(4) ?
C22 C23 C30 O32 . . . . 86.2(5) ?
C24 C23 C30 O32 . . . . -94.5(5) ?
C22 C23 C30 O31 . . . . -92.7(4) ?
C24 C23 C30 O31 . . . . 86.6(4) ?
C46 C41 C42 C43 . . . . -1.1(6) ?
C47 C41 C42 C43 . . . . -178.3(4) ?
C46 C41 C42 Br7 . . . . 176.2(3) ?
C47 C41 C42 Br7 . . . . -1.0(5) ?
C41 C42 C43 C44 . . . . 0.9(5) ?
Br7 C42 C43 C44 . . . . -176.4(3) ?
C41 C42 C43 C50 . . . . 179.8(4) ?
Br7 C42 C43 C50 . . . . 2.5(5) ?
C42 C43 C44 C45 . . . . 0.1(5) ?
C50 C43 C44 C45 . . . . -178.9(4) ?
C42 C43 C44 Br8 . . . . -179.2(3) ?
C50 C43 C44 Br8 . . . . 1.9(5) ?
C43 C44 C45 N53 . . . . 176.1(4) ?
Br8 C44 C45 N53 . . . . -4.7(5) ?
C43 C44 C45 C46 . . . . -0.7(5) ?
Br8 C44 C45 C46 . . . . 178.5(3) ?
C42 C41 C46 C45 . . . . 0.3(6) ?
C47 C41 C46 C45 . . . . 177.5(4) ?
C42 C41 C46 Br9 . . . . 179.4(3) ?
C47 C41 C46 Br9 . . . . -3.4(5) ?
N53 C45 C46 C41 . . . . -176.3(4) ?
C44 C45 C46 C41 . . . . 0.5(5) ?
N53 C45 C46 Br9 . . . . 4.6(5) ?
C44 C45 C46 Br9 . . . . -178.6(3) ?
C46 C41 C47 O48 . . . . -82.0(5) ?
C42 C41 C47 O48 . . . . 95.1(5) ?
C46 C41 C47 O49 . . . . 98.1(4) ?
C42 C41 C47 O49 . . . . -84.7(5) ?
C42 C43 C50 O51 . . . . 80.9(5) ?
C44 C43 C50 O51 . . . . -100.2(5) ?
C42 C43 C50 O52 . . . . -96.8(4) ?
C44 C43 C50 O52 . . . . 82.2(4) ?
C66 C61 C62 C63 . . . . 0.6(5) ?
C67 C61 C62 C63 . . . . -178.1(4) ?
C66 C61 C62 Br10 . . . . -178.7(3) ?
C67 C61 C62 Br10 . . . . 2.5(5) ?
C61 C62 C63 C64 . . . . -0.8(5) ?
Br10 C62 C63 C64 . . . . 178.6(3) ?
C61 C62 C63 C70 . . . . 176.9(4) ?
Br10 C62 C63 C70 . . . . -3.8(5) ?
C62 C63 C64 C65 . . . . -0.1(6) ?
C70 C63 C64 C65 . . . . -177.7(4) ?
C62 C63 C64 Br11 . . . . 176.2(3) ?
C70 C63 C64 Br11 . . . . -1.5(5) ?
C63 C64 C65 N73 . . . . -179.2(4) ?
Br11 C64 C65 N73 . . . . 4.5(5) ?
C63 C64 C65 C66 . . . . 1.0(5) ?
Br11 C64 C65 C66 . . . . -175.4(3) ?
C62 C61 C66 C65 . . . . 0.4(5) ?
C67 C61 C66 C65 . . . . 179.2(4) ?
C62 C61 C66 Br12 . . . . -176.8(3) ?
C67 C61 C66 Br12 . . . . 2.0(5) ?
N73 C65 C66 C61 . . . . 179.0(4) ?
C64 C65 C66 C61 . . . . -1.1(5) ?
N73 C65 C66 Br12 . . . . -3.9(5) ?
C64 C65 C66 Br12 . . . . 176.0(3) ?
C66 C61 C67 O69 . . . . 82.4(5) ?
C62 C61 C67 O69 . . . . -98.9(5) ?
C66 C61 C67 O68 . . . . -95.8(4) ?
C62 C61 C67 O68 . . . . 83.0(5) ?
C64 C63 C70 O71 . . . . 97.8(5) ?
C62 C63 C70 O71 . . . . -79.8(5) ?
C64 C63 C70 O72 . . . . -82.8(5) ?
C62 C63 C70 O72 . . . . 99.6(4) ?
