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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/48/4504814.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_4504814
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Salmon, Debra J.'
'Smith, Michelle M.'
'Desper, John'
_publ_section_title
;
 Cyanophenyloximes:  Reliable and Versatile Tools for Hydrogen-Bond
 Directed Supramolecular Synthesis of Cocrystals
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1033
_journal_paper_doi               10.1021/cg0600492
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety
;
(C8 H5 Br N2 O)2 (C14 H14 N4)
;
_chemical_formula_sum            'C30 H24 Br2 N8 O2'
_chemical_formula_weight         688.39
_chemical_name_systematic
;
(4-bromo-phenylacetonitrile oxime)2, 1,4-di[(1-imidazolyl)methyl]benzene
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.4500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9436(5)
_cell_length_b                   5.1863(2)
_cell_length_c                   21.6419(9)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.05
_cell_measurement_theta_min      2.48
_cell_volume                     1450.17(10)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω 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  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15907
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    2.839
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4257
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0245
_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)+(0.0450P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0688
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                3913
_reflns_number_total             4257
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0600492si20060201_122733.cif
_cod_data_source_block           1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4504814
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_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
Br1 Br 0.619848(9) 1.21027(3) 0.148475(6) 0.02163(6) Uani 1 1 d .
N11 N 0.11690(8) -0.1405(2) 0.34981(5) 0.01617(18) Uani 1 1 d .
C12 C 0.09453(10) -0.1885(2) 0.28923(6) 0.0185(2) Uani 1 1 d .
H12 H 0.0526 -0.3276 0.2740 0.022 Uiso 1 1 calc R
N13 N 0.13828(8) -0.0174(2) 0.25369(5) 0.0199(2) Uani 1 1 d .
C14 C 0.19234(10) 0.1481(3) 0.29409(6) 0.0191(2) Uani 1 1 d .
H14 H 0.2321 0.2917 0.2822 0.023 Uiso 1 1 calc R
C15 C 0.17970(9) 0.0736(2) 0.35371(6) 0.0184(2) Uani 1 1 d .
H15 H 0.2084 0.1533 0.3904 0.022 Uiso 1 1 calc R
C21 C 0.04238(9) -0.1403(2) 0.45237(5) 0.0166(2) Uani 1 1 d .
C22 C 0.06942(10) -0.1986(2) 0.51411(6) 0.0181(2) Uani 1 1 d .
H22 H 0.1168 -0.3344 0.5240 0.042 Uiso 1 1 calc R
C26 C -0.02728(9) 0.0584(2) 0.43861(5) 0.0184(2) Uani 1 1 d .
H26 H -0.0463 0.0990 0.3967 0.042 Uiso 1 1 calc R
C27 C 0.08693(11) -0.2995(2) 0.40187(6) 0.0192(2) Uani 1 1 d .
H27A H 0.1484 -0.3943 0.4193 0.023 Uiso 1 1 calc R
H27B H 0.0349 -0.4281 0.3866 0.023 Uiso 1 1 calc R
C31 C 0.36449(9) 0.5807(2) 0.11557(5) 0.0173(2) Uani 1 1 d .
C32 C 0.37926(11) 0.7005(3) 0.17325(6) 0.0210(2) Uani 1 1 d .
H32 H 0.3372 0.6528 0.2059 0.025 Uiso 1 1 calc R
C33 C 0.45460(10) 0.8882(3) 0.18338(6) 0.0222(2) Uani 1 1 d .
H33 H 0.4642 0.9697 0.2226 0.027 Uiso 1 1 calc R
C34 C 0.51602(9) 0.9555(3) 0.13521(6) 0.0189(2) Uani 1 1 d .
C35 C 0.50223(10) 0.8412(3) 0.07750(6) 0.0213(2) Uani 1 1 d .
H35 H 0.5445 0.8894 0.0450 0.026 Uiso 1 1 calc R
C36 C 0.42585(10) 0.6550(3) 0.06766(6) 0.0204(2) Uani 1 1 d .
H36 H 0.4152 0.5776 0.0280 0.024 Uiso 1 1 calc R
C37 C 0.28767(9) 0.3726(3) 0.10617(5) 0.0176(2) Uani 1 1 d .
N37 N 0.24024(9) 0.2847(2) 0.15253(5) 0.0197(2) Uani 1 1 d .
O37 O 0.17310(7) 0.0871(2) 0.13718(4) 0.02228(19) Uani 1 1 d .
H37 H 0.1531(14) 0.049(4) 0.1726(9) 0.027 Uiso 1 1 d .
C38 C 0.27093(10) 0.2622(3) 0.04494(6) 0.0198(2) Uani 1 1 d .
N38 N 0.26141(10) 0.1785(3) -0.00401(6) 0.0259(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 0.0000 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
C12 N11 C15 107.46(10) . .
C12 N11 C27 126.26(11) . .
C15 N11 C27 126.10(10) . .
N13 C12 N11 111.53(11) . .
N13 C12 H12 124.2 . .
N11 C12 H12 124.2 . .
C12 N13 C14 105.44(10) . .
C15 C14 N13 109.65(11) . .
C15 C14 H14 125.2 . .
N13 C14 H14 125.2 . .
C14 C15 N11 105.92(11) . .
C14 C15 H15 127.0 . .
N11 C15 H15 127.0 . .
C26 C21 C22 119.23(11) . .
C26 C21 C27 121.40(11) . .
C22 C21 C27 119.35(11) . .
C26 C22 C21 120.29(11) 3_556 .
C26 C22 H22 119.9 3_556 .
C21 C22 H22 119.9 . .
C21 C26 C22 120.48(11) . 3_556
C21 C26 H26 119.8 . .
C22 C26 H26 119.8 3_556 .
N11 C27 C21 112.22(10) . .
N11 C27 H27A 109.2 . .
C21 C27 H27A 109.2 . .
N11 C27 H27B 109.2 . .
C21 C27 H27B 109.2 . .
H27A C27 H27B 107.9 . .
C32 C31 C36 119.13(12) . .
C32 C31 C37 120.27(11) . .
C36 C31 C37 120.57(11) . .
C33 C32 C31 120.72(12) . .
C33 C32 H32 119.6 . .
C31 C32 H32 119.6 . .
C32 C33 C34 119.05(12) . .
C32 C33 H33 120.5 . .
C34 C33 H33 120.5 . .
C35 C34 C33 121.29(12) . .
C35 C34 Br1 119.16(9) . .
C33 C34 Br1 119.55(10) . .
C34 C35 C36 119.20(12) . .
C34 C35 H35 120.4 . .
C36 C35 H35 120.4 . .
C35 C36 C31 120.59(12) . .
C35 C36 H36 119.7 . .
C31 C36 H36 119.7 . .
N37 C37 C38 121.33(12) . .
N37 C37 C31 120.01(11) . .
C38 C37 C31 118.59(10) . .
C37 N37 O37 113.56(10) . .
N37 O37 H37 100.4(13) . .
N38 C38 C37 177.32(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C34 1.8942(12) .
N11 C12 1.3487(15) .
N11 C15 1.3757(16) .
N11 C27 1.4672(15) .
C12 N13 1.3236(16) .
C12 H12 0.9500 .
N13 C14 1.3848(17) .
C14 C15 1.3662(17) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C21 C26 1.3899(17) .
C21 C22 1.3938(17) .
C21 C27 1.5115(17) .
C22 C26 1.3929(17) 3_556
C22 H22 0.9500 .
C26 C22 1.3929(17) 3_556
C26 H26 0.9500 .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C31 C32 1.3971(18) .
C31 C36 1.3978(16) .
C31 C37 1.4734(17) .
C32 C33 1.3859(18) .
C32 H32 0.9500 .
C33 C34 1.3929(17) .
C33 H33 0.9500 .
C34 C35 1.3844(18) .
C35 C36 1.3890(18) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C37 N37 1.2905(16) .
C37 C38 1.4479(17) .
N37 O37 1.3717(14) .
O37 H37 0.848(19) .
C38 N38 1.1447(19) .
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
O37 H37 N13 0.848(19) 1.810(19) 2.6441(14) 167.8(18)
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_4
C15 N11 C12 N13 -0.51(14) .
C27 N11 C12 N13 -175.92(11) .
N11 C12 N13 C14 0.45(14) .
C12 N13 C14 C15 -0.23(14) .
N13 C14 C15 N11 -0.07(14) .
C12 N11 C15 C14 0.34(14) .
C27 N11 C15 C14 175.76(11) .
C26 C21 C22 C26 -0.2(2) 3_556
C27 C21 C22 C26 -178.41(12) 3_556
C22 C21 C26 C22 0.2(2) 3_556
C27 C21 C26 C22 178.37(12) 3_556
C12 N11 C27 C21 -133.21(13) .
C15 N11 C27 C21 52.20(16) .
C26 C21 C27 N11 42.75(17) .
C22 C21 C27 N11 -139.09(12) .
C36 C31 C32 C33 -0.9(2) .
C37 C31 C32 C33 177.01(12) .
C31 C32 C33 C34 -0.3(2) .
C32 C33 C34 C35 0.9(2) .
C32 C33 C34 Br1 -179.64(10) .
C33 C34 C35 C36 -0.3(2) .
Br1 C34 C35 C36 -179.75(10) .
C34 C35 C36 C31 -0.9(2) .
C32 C31 C36 C35 1.5(2) .
C37 C31 C36 C35 -176.38(12) .
C32 C31 C37 N37 -6.08(19) .
C36 C31 C37 N37 171.79(13) .
C32 C31 C37 C38 176.92(12) .
C36 C31 C37 C38 -5.21(18) .
C38 C37 N37 O37 -1.45(18) .
C31 C37 N37 O37 -178.37(11) .
N37 C37 C38 N38 -156(3) .
C31 C37 C38 N38 21(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139145633
