#------------------------------------------------------------------------------
#$Date: 2019-09-18 13:40:29 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200256.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_7200256
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Salmon, Debra J.'
'Smith, Michelle M.'
'Desper, John'
_publ_section_title
;
 Cyanooximes as effective and selective co-crystallizing agents
;
_journal_coden_ASTM              CRECF4
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              439
_journal_page_last               443
_journal_paper_doi               10.1039/b811322j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety
;
(C8 H5 Br N2 O) (C14 H11 Br N2)
;
_chemical_formula_sum            'C22 H16 Br2 N4 O'
_chemical_formula_weight         512.21
_chemical_name_common
'(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole'
_chemical_name_systematic
;
(4-bromo-PhC(CN)(=NOH)), 1-(4-bromobenzyl)benzimidazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.536(2)
_cell_angle_beta                 99.505(2)
_cell_angle_gamma                94.752(2)
_cell_formula_units_Z            2
_cell_length_a                   5.3033(6)
_cell_length_b                   13.2294(15)
_cell_length_c                   15.0601(17)
_cell_measurement_reflns_used    6500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.35
_cell_volume                     1009.5(2)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0270
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11582
_diffrn_reflns_theta_full        30.05
_diffrn_reflns_theta_max         30.05
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    4.036
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.519
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.685
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             508
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         5763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0271
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.0800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0736
_reflns_number_gt                4972
_reflns_number_total             5763
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B811322J.txt
_cod_data_source_block           A3
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200256
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Br1 Br 0.23446(3) 0.130843(14) -0.100585(11) 0.02864(6) Uani 1 1 d . . .
Br2 Br -0.26182(3) 0.594556(12) 0.943098(11) 0.02674(6) Uani 1 1 d . . .
N11 N 0.7222(2) 0.20505(10) 0.36245(9) 0.0205(2) Uani 1 1 d . . .
C12 C 0.6814(3) 0.15263(13) 0.42790(10) 0.0227(3) Uani 1 1 d . . .
H12 H 0.7577 0.0916 0.4349 0.027 Uiso 1 1 calc R . .
N13 N 0.5251(3) 0.19506(11) 0.48079(9) 0.0231(3) Uani 1 1 d . . .
C14 C 0.4559(3) 0.28111(12) 0.44730(10) 0.0200(3) Uani 1 1 d . . .
C15 C 0.2866(3) 0.35243(13) 0.47458(11) 0.0229(3) Uani 1 1 d . . .
H15 H 0.1998 0.3481 0.5242 0.028 Uiso 1 1 calc R . .
C16 C 0.2509(3) 0.42954(13) 0.42628(11) 0.0247(3) Uani 1 1 d . . .
H16 H 0.1358 0.4786 0.4429 0.030 Uiso 1 1 calc R . .
C17 C 0.3800(3) 0.43723(13) 0.35342(11) 0.0240(3) Uani 1 1 d . . .
H17 H 0.3528 0.4921 0.3228 0.029 Uiso 1 1 calc R . .
C18 C 0.5459(3) 0.36667(13) 0.32523(11) 0.0224(3) Uani 1 1 d . . .
H18 H 0.6328 0.3714 0.2756 0.027 Uiso 1 1 calc R . .
C19 C 0.5790(3) 0.28848(12) 0.37322(10) 0.0193(3) Uani 1 1 d . . .
C21 C 0.4374(3) 0.14174(12) 0.01856(10) 0.0212(3) Uani 1 1 d . . .
C22 C 0.6791(3) 0.19932(12) 0.04224(11) 0.0224(3) Uani 1 1 d . . .
H22 H 0.7472 0.2308 -0.0012 0.027 Uiso 1 1 calc R . .
C23 C 0.8194(3) 0.20998(12) 0.13078(11) 0.0210(3) Uani 1 1 d . . .
H23 H 0.9853 0.2494 0.1481 0.025 Uiso 1 1 calc R . .
C24 C 0.7209(3) 0.16379(12) 0.19472(10) 0.0193(3) Uani 1 1 d . . .
C25 C 0.4796(3) 0.10480(12) 0.16856(11) 0.0218(3) Uani 1 1 d . . .
H25 H 0.4125 0.0719 0.2113 0.026 Uiso 1 1 calc R . .
C26 C 0.3359(3) 0.09369(12) 0.08019(11) 0.0222(3) Uani 1 1 d . . .
H26 H 0.1707 0.0538 0.0624 0.027 Uiso 1 1 calc R . .
C27 C 0.8775(3) 0.17743(13) 0.29080(11) 0.0230(3) Uani 1 1 d . . .
H27A H 0.9492 0.1117 0.2959 0.028 Uiso 1 1 calc R . .
H27B H 1.0235 0.2329 0.3010 0.028 Uiso 1 1 calc R . .
C31 C -0.0552(3) 0.30103(12) 0.74697(10) 0.0204(3) Uani 1 1 d . . .
C32 C 0.0847(3) 0.39889(13) 0.75905(11) 0.0229(3) Uani 1 1 d . . .
H32 H 0.2204 0.4060 0.7260 0.027 Uiso 1 1 calc R . .
C33 C 0.0273(3) 0.48555(13) 0.81884(11) 0.0232(3) Uani 1 1 d . . .
H33 H 0.1239 0.5519 0.8275 0.028 Uiso 1 1 calc R . .
C34 C -0.1741(3) 0.47412(12) 0.86604(10) 0.0214(3) Uani 1 1 d . . .
C35 C -0.3143(3) 0.37825(13) 0.85578(11) 0.0230(3) Uani 1 1 d . . .
H35 H -0.4499 0.3715 0.8890 0.028 Uiso 1 1 calc R . .
C36 C -0.2540(3) 0.29203(13) 0.79621(11) 0.0226(3) Uani 1 1 d . . .
H36 H -0.3493 0.2257 0.7887 0.027 Uiso 1 1 calc R . .
C37 C 0.0083(3) 0.20877(12) 0.68401(10) 0.0209(3) Uani 1 1 d . . .
N37 N 0.1827(3) 0.21829(11) 0.63470(9) 0.0234(3) Uani 1 1 d . . .
O37 O 0.2217(2) 0.12539(9) 0.58132(8) 0.0265(2) Uani 1 1 d . . .
H37 H 0.343(4) 0.1444(17) 0.5500(15) 0.032 Uiso 1 1 d . . .
C38 C -0.1244(3) 0.10712(13) 0.67962(11) 0.0244(3) Uani 1 1 d . . .
N38 N -0.2271(3) 0.02743(12) 0.67896(11) 0.0321(3) 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 0.0000 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N11 C19 106.91(12) . . ?
C12 N11 C27 127.27(13) . . ?
C19 N11 C27 125.76(13) . . ?
N13 C12 N11 113.06(14) . . ?
N13 C12 H12 123.5 . . ?
N11 C12 H12 123.5 . . ?
C12 N13 C14 105.17(13) . . ?
N13 C14 C19 109.42(13) . . ?
N13 C14 C15 130.30(14) . . ?
C19 C14 C15 120.25(14) . . ?
C16 C15 C14 117.28(14) . . ?
C16 C15 H15 121.4 . . ?
C14 C15 H15 121.4 . . ?
C15 C16 C17 121.80(14) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 121.49(15) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 116.56(14) . . ?
C17 C18 H18 121.7 . . ?
C19 C18 H18 121.7 . . ?
N11 C19 C18 131.95(14) . . ?
N11 C19 C14 105.44(13) . . ?
C18 C19 C14 122.61(14) . . ?
C22 C21 C26 121.78(14) . . ?
C22 C21 Br1 119.42(12) . . ?
C26 C21 Br1 118.79(12) . . ?
C21 C22 C23 118.50(14) . . ?
C21 C22 H22 120.7 . . ?
C23 C22 H22 120.7 . . ?
C22 C23 C24 121.04(14) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 H23 119.5 . . ?
C25 C24 C23 119.26(14) . . ?
C25 C24 C27 120.93(14) . . ?
C23 C24 C27 119.81(14) . . ?
C26 C25 C24 120.43(14) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C21 C26 C25 118.97(14) . . ?
C21 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
N11 C27 C24 111.82(12) . . ?
N11 C27 H27A 109.3 . . ?
C24 C27 H27A 109.3 . . ?
N11 C27 H27B 109.3 . . ?
C24 C27 H27B 109.3 . . ?
H27A C27 H27B 107.9 . . ?
C36 C31 C32 118.92(14) . . ?
C36 C31 C37 120.68(14) . . ?
C32 C31 C37 120.39(13) . . ?
C33 C32 C31 120.56(14) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.06(15) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C35 C34 C33 121.53(14) . . ?
C35 C34 Br2 119.78(11) . . ?
C33 C34 Br2 118.66(12) . . ?
C34 C35 C36 118.86(14) . . ?
C34 C35 H35 120.6 . . ?
C36 C35 H35 120.6 . . ?
C35 C36 C31 121.06(15) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
N37 C37 C38 120.57(14) . . ?
N37 C37 C31 120.51(14) . . ?
C38 C37 C31 118.91(13) . . ?
C37 N37 O37 113.26(13) . . ?
N37 O37 H37 103.2(14) . . ?
N38 C38 C37 177.96(18) . . ?
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
Br1 C21 1.9035(15) . ?
Br2 C34 1.8973(15) . ?
N11 C12 1.357(2) . ?
N11 C19 1.3867(19) . ?
N11 C27 1.4656(18) . ?
C12 N13 1.318(2) . ?
C12 H12 0.9500 . ?
N13 C14 1.394(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.400(2) . ?
C15 C16 1.384(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(2) . ?
C18 H18 0.9500 . ?
C21 C22 1.386(2) . ?
C21 C26 1.386(2) . ?
C22 C23 1.387(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.394(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.392(2) . ?
C24 C27 1.510(2) . ?
C25 C26 1.391(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C31 C36 1.397(2) . ?
C31 C32 1.398(2) . ?
C31 C37 1.474(2) . ?
C32 C33 1.385(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.393(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(2) . ?
C35 C36 1.385(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 N37 1.2923(19) . ?
C37 C38 1.448(2) . ?
N37 O37 1.3666(18) . ?
O37 H37 0.91(2) . ?
C38 N38 1.143(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O37 H37 N13 0.91(2) 1.73(2) 2.6260(18) 168(2) .
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
C19 N11 C12 N13 -0.37(18) . . . . ?
C27 N11 C12 N13 -177.81(14) . . . . ?
N11 C12 N13 C14 0.57(18) . . . . ?
C12 N13 C14 C19 -0.55(16) . . . . ?
C12 N13 C14 C15 177.26(16) . . . . ?
N13 C14 C15 C16 -178.37(15) . . . . ?
C19 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C18 1.2(2) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C12 N11 C19 C18 -179.23(16) . . . . ?
C27 N11 C19 C18 -1.7(3) . . . . ?
C12 N11 C19 C14 0.00(16) . . . . ?
C27 N11 C19 C14 177.49(14) . . . . ?
C17 C18 C19 N11 178.16(15) . . . . ?
C17 C18 C19 C14 -1.0(2) . . . . ?
N13 C14 C19 N11 0.34(16) . . . . ?
C15 C14 C19 N11 -177.73(13) . . . . ?
N13 C14 C19 C18 179.66(14) . . . . ?
C15 C14 C19 C18 1.6(2) . . . . ?
C26 C21 C22 C23 -1.1(2) . . . . ?
Br1 C21 C22 C23 177.29(11) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 1.0(2) . . . . ?
C22 C23 C24 C27 -179.57(14) . . . . ?
C23 C24 C25 C26 -1.3(2) . . . . ?
C27 C24 C25 C26 179.31(14) . . . . ?
C22 C21 C26 C25 0.8(2) . . . . ?
Br1 C21 C26 C25 -177.56(11) . . . . ?
C24 C25 C26 C21 0.4(2) . . . . ?
C12 N11 C27 C24 122.20(16) . . . . ?
C19 N11 C27 C24 -54.8(2) . . . . ?
C25 C24 C27 N11 -47.02(19) . . . . ?
C23 C24 C27 N11 133.55(14) . . . . ?
C36 C31 C32 C33 0.0(2) . . . . ?
C37 C31 C32 C33 -179.35(14) . . . . ?
C31 C32 C33 C34 -0.7(2) . . . . ?
C32 C33 C34 C35 1.2(2) . . . . ?
C32 C33 C34 Br2 -176.98(12) . . . . ?
C33 C34 C35 C36 -0.8(2) . . . . ?
Br2 C34 C35 C36 177.35(12) . . . . ?
C34 C35 C36 C31 0.0(2) . . . . ?
C32 C31 C36 C35 0.4(2) . . . . ?
C37 C31 C36 C35 179.75(14) . . . . ?
C36 C31 C37 N37 176.15(14) . . . . ?
C32 C31 C37 N37 -4.5(2) . . . . ?
C36 C31 C37 C38 -5.0(2) . . . . ?
C32 C31 C37 C38 174.35(14) . . . . ?
C38 C37 N37 O37 0.1(2) . . . . ?
C31 C37 N37 O37 178.92(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653535
