#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/97/2229767.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_2229767
loop_
_publ_author_name
'Rivera, Augusto'
'Quiroga, Diego'
'Ríos-Motta, Jaime'
'Dušek, Michal'
'Fejfarová, Karla'
_publ_section_title
;
 4,4'-Dibromo-2,2'-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylidene)}diphenol
;
_journal_coeditor_code           NG5118
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o753
_journal_paper_doi               10.1107/S1600536811006489
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C21 H24 Br2 N2 O2'
_chemical_formula_moiety         'C21 H24 Br2 N2 O2'
_chemical_formula_sum            'C21 H24 Br2 N2 O2'
_chemical_formula_weight         496.2
_chemical_name_systematic
;
4,4'-Dibromo-2,2'-{[(3aS,7aS)-2,3,3a,4,5,6,7,7a-octahydro-
1H-1,3-benzimidazole-1,3-diyl]bis(methylidene)}diphenol
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9645(2)
_cell_length_b                   18.5497(4)
_cell_length_c                   9.0494(2)
_cell_measurement_reflns_used    16248
_cell_measurement_temperature    120
_cell_measurement_theta_max      66.5363
_cell_measurement_theta_min      4.7602
_cell_volume                     1001.22(5)
_computing_cell_refinement       'Crysalis RED (Oxford Diffraction, 2009)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2009)'
_computing_data_reduction        'Crysalis RED (Oxford Diffraction, 2009)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006 (Petříček et al., 2006)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur diffractometer with an Atlas detector
;
_diffrn_measurement_method       'Rotation method data acquisition using ω'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0038
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17493
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program Crysalis RED
(Oxford diffraction, 2008). The same program was used for indexing of the
crystal shape and absorption correction.
;
_diffrn_reflns_theta_full        66.78
_diffrn_reflns_theta_max         66.78
_diffrn_reflns_theta_min         4.77
_exptl_absorpt_coefficient_mu    5.323
_exptl_absorpt_correction_T_max  0.678
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(CrysAlisPro; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.6455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.1935
_exptl_crystal_size_mid          0.1321
_exptl_crystal_size_min          0.0952
_refine_diff_density_max         0.11
_refine_diff_density_min         -0.12
_refine_ls_abs_structure_details 'Flack (1983), 670 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    45
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1749
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0146
_refine_ls_R_factor_gt           0.0145
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/[σ²(I)+0.0016I²]
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0493
_reflns_number_gt                1739
_reflns_number_total             1749
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            ng5118.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     'P 2 2ab '
_cod_database_code               2229767
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,z
3 -x+1/2,y+1/2,-z
4 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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.55638(3) 0.229059(8) 0.146172(18) 0.02610(7) Uani d . 1 . .
O O1 0.99958(19) 0.42005(6) 0.59844(13) 0.0226(3) Uani d . 1 . .
N N1 0.59652(10) 0.44416(5) 0.71146(11) 0.0163(4) Uani d . 1 . .
C C1 0.5 0.5 0.61175(12) 0.0154(6) Uani d . 1 . .
C C2 0.5511(3) 0.36959(8) 0.66196(17) 0.0165(4) Uani d . 1 . .
C C3 0.6757(3) 0.35153(7) 0.52184(17) 0.0156(4) Uani d . 1 . .
C C4 0.8947(3) 0.37777(8) 0.49815(18) 0.0174(4) Uani d . 1 . .
C C5 1.0085(3) 0.35992(9) 0.36866(19) 0.0204(4) Uani d . 1 . .
C C6 0.9120(3) 0.31499(8) 0.26478(18) 0.0205(5) Uani d . 1 . .
C C7 0.6975(3) 0.28860(8) 0.29074(18) 0.0180(4) Uani d . 1 . .
C C8 0.5810(2) 0.30615(8) 0.41680(17) 0.0160(4) Uani d . 1 . .
C C9 0.5029(3) 0.45921(8) 0.85825(17) 0.0179(4) Uani d . 1 . .
C C10 0.6319(3) 0.43125(9) 0.99165(18) 0.0268(5) Uani d . 1 . .
C C11 0.5129(4) 0.45880(10) 1.13117(19) 0.0322(6) Uani d . 1 . .
H H1a 0.382527 0.479008 0.553376 0.0185 Uiso d . 1 . .
H H2a 0.39302 0.363598 0.646178 0.0198 Uiso d . 1 . .
H H2b 0.593539 0.336399 0.738387 0.0198 Uiso d . 1 . .
H H5 1.155662 0.379087 0.351434 0.0245 Uiso d . 1 . .
H H6 0.991627 0.302257 0.176355 0.0245 Uiso d . 1 . .
H H8 0.433442 0.286947 0.43234 0.0192 Uiso d . 1 . .
H H9 0.362416 0.434666 0.870296 0.0214 Uiso d . 1 . .
H H10a 0.782412 0.449589 0.989185 0.0322 Uiso d . 1 . .
H H10b 0.63082 0.3795 0.991145 0.0322 Uiso d . 1 . .
H H11a 0.5957 0.444143 1.217041 0.0386 Uiso d . 1 . .
H H11b 0.367722 0.43676 1.138666 0.0386 Uiso d . 1 . .
H H1o 0.904(3) 0.4361(12) 0.657(2) 0.0272 Uiso d . 1 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
Br -0.6763 1.2805 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
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_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O1 H1o . . . 108.6(14) no
C1 N1 C2 . . . 113.34(9) no
C1 N1 C9 . . . 105.60(9) no
C2 N1 C9 . . . 112.48(10) no
N1 C1 N1 . . 2_665 105.43(9) no
N1 C1 H1a . . . 109.4713 no
N1 C1 H1a . . 2_665 109.4712 no
N1 C1 H1a 2_665 . . 109.4712 no
N1 C1 H1a 2_665 . 2_665 109.4713 no
H1a C1 H1a . . 2_665 113.2317 no
N1 C2 C3 . . . 111.86(12) no
N1 C2 H2a . . . 109.4713 no
N1 C2 H2b . . . 109.4715 no
C3 C2 H2a . . . 109.471 no
C3 C2 H2b . . . 109.4709 no
H2a C2 H2b . . . 106.9725 no
C2 C3 C4 . . . 120.52(13) no
C2 C3 C8 . . . 120.64(14) no
C4 C3 C8 . . . 118.78(14) no
O1 C4 C3 . . . 121.76(14) no
O1 C4 C5 . . . 118.47(13) no
C3 C4 C5 . . . 119.78(14) no
C4 C5 C6 . . . 120.83(14) no
C4 C5 H5 . . . 119.5819 no
C6 C5 H5 . . . 119.5833 no
C5 C6 C7 . . . 118.73(15) no
C5 C6 H6 . . . 120.6356 no
C7 C6 H6 . . . 120.636 no
Br1 C7 C6 . . . 119.62(12) no
Br1 C7 C8 . . . 118.88(12) no
C6 C7 C8 . . . 121.48(15) no
C3 C8 C7 . . . 120.37(14) no
C3 C8 H8 . . . 119.8142 no
C7 C8 H8 . . . 119.8142 no
N1 C9 C9 . . 2_665 101.48(12) no
N1 C9 C10 . . . 117.42(13) no
N1 C9 H9 . . . 110.1556 no
C9 C9 C10 2_665 . . 110.62(13) no
C9 C9 H9 2_665 . . 117.0073 no
C10 C9 H9 . . . 100.9265 no
C9 C10 C11 . . . 107.74(15) no
C9 C10 H10a . . . 109.471 no
C9 C10 H10b . . . 109.4714 no
C11 C10 H10a . . . 109.4709 no
C11 C10 H10b . . . 109.4716 no
H10a C10 H10b . . . 111.1472 no
C10 C11 C11 . . 2_665 112.17(15) no
C10 C11 H11a . . . 109.4713 no
C10 C11 H11b . . . 109.4711 no
C11 C11 H11a 2_665 . . 109.4712 no
C11 C11 H11b 2_665 . . 109.4713 no
H11a C11 H11b . . . 106.632 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C7 . . 1.9080(16) no
O1 C4 . . 1.353(2) no
O1 H1o . . 0.84(2) no
N1 C1 . . 1.4895(12) no
N1 C2 . . 1.4789(18) no
N1 C9 . . 1.4677(18) no
C1 H1a . . 0.96 no
C1 H1a . 2_665 0.96 no
C2 C3 . . 1.507(2) no
C2 H2a . . 0.96 no
C2 H2b . . 0.96 no
C3 C4 . . 1.410(2) no
C3 C8 . . 1.390(2) no
C4 C5 . . 1.394(2) no
C5 C6 . . 1.382(2) no
C5 H5 . . 0.96 no
C6 C7 . . 1.390(2) no
C6 H6 . . 0.96 no
C7 C8 . . 1.375(2) no
C8 H8 . . 0.96 no
C9 C9 . 2_665 1.514(2) no
C9 C10 . . 1.523(2) no
C9 H9 . . 0.96 no
C10 C11 . . 1.536(3) no
C10 H10a . . 0.96 no
C10 H10b . . 0.96 no
C11 C11 . 2_665 1.536(3) no
C11 H11a . . 0.96 no
C11 H11b . . 0.96 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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 N1 . . . 0.833(19) 1.905(18) 2.6506(13) 148.3(19) yes
C1 H1a O1 . . 1_455 0.96 2.57 3.3351(11) 137 yes
C8 H8 Cg2 . . 4_465 0.96 2.85 3.5407(16) 130 yes
C11 H11b Cg2 . . 1_565 0.96 2.86 3.728(2) 150 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
C2 N1 C1 N1 . . . 2_665 138.00(9) ?
C9 N1 C1 N1 . . . 2_665 14.44(9) ?
C1 N1 C2 C3 . . . . 68.53(14) ?
C9 N1 C2 C3 . . . . -171.77(12) ?
C1 N1 C9 C10 . . . . -157.29(11) ?
C1 N1 C9 C9 . . . 2_665 -36.62(13) ?
C2 N1 C9 C10 . . . . 78.61(16) ?
C2 N1 C9 C9 . . . 2_665 -160.72(12) ?
N1 C2 C3 C4 . . . . 37.37(19) ?
N1 C2 C3 C8 . . . . -145.54(13) ?
C2 C3 C4 O1 . . . . -0.5(2) ?
C2 C3 C4 C5 . . . . 179.31(14) ?
C8 C3 C4 O1 . . . . -177.62(14) ?
C8 C3 C4 C5 . . . . 2.2(2) ?
C2 C3 C8 C7 . . . . -178.55(14) ?
C4 C3 C8 C7 . . . . -1.4(2) ?
O1 C4 C5 C6 . . . . 177.87(15) ?
C3 C4 C5 C6 . . . . -1.9(2) ?
C4 C5 C6 C7 . . . . 0.9(2) ?
C5 C6 C7 Br1 . . . . 177.93(12) ?
C5 C6 C7 C8 . . . . -0.1(2) ?
Br1 C7 C8 C3 . . . . -177.66(11) ?
C6 C7 C8 C3 . . . . 0.4(2) ?
N1 C9 C10 C11 . . . . 175.39(13) ?
C9 C9 C10 C11 2_665 . . . 59.64(18) ?
N1 C9 C9 N1 . . 2_665 2_665 45.12(14) ?
N1 C9 C9 C10 . . 2_665 2_665 170.46(12) ?
C10 C9 C9 N1 . . 2_665 2_665 170.46(12) ?
C10 C9 C9 C10 . . 2_665 2_665 -64.21(18) ?
C9 C10 C11 C11 . . . 2_665 -55.1(2) ?
C10 C11 C11 C10 . . 2_665 2_665 54.8(2) ?
