#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/70/2227041.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_2227041
loop_
_publ_author_name
'Yang, Yu-Hua'
'Wu, Jian-Chao'
'Gong, Shang-Sheng'
'Wang, Jiu-Si'
_publ_section_title
;
 4-Bromo-2-({4-[(hydroxyimino)methyl]phenyl}iminomethyl)phenol
;
_journal_coeditor_code           PV2295
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2014
_journal_paper_doi               10.1107/S160053681002698X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H11 Br N2 O2'
_chemical_formula_moiety         'C14 H11 Br N2 O2'
_chemical_formula_sum            'C14 H11 Br N2 O2'
_chemical_formula_weight         319.16
_chemical_melting_point_gt       490
_chemical_melting_point_lt       491
_chemical_name_common
;
4-[1-(hydroxyimino)methyl]-N-(2-hydroxy-5-bromobenzylidene)aniline
;
_chemical_name_systematic
;
4-Bromo-2-({4-[(hydroxyimino)methyl]phenyl}iminomethyl)phenol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.4279(5)
_cell_length_b                   12.1790(16)
_cell_length_c                   23.196(2)
_cell_measurement_reflns_used    4929
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      32.90
_cell_measurement_theta_min      1.90
_cell_volume                     1250.9(2)
_computing_cell_refinement       'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_collection       'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku/MSC, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            15336
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.92
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.285
_exptl_absorpt_correction_T_max  0.5319
_exptl_absorpt_correction_T_min  0.4822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2009)'
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.442
_refine_ls_abs_structure_details 'Flack (1983), 1615 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.022(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.851
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         4346
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.851
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0171P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0520
_refine_ls_wR_factor_ref         0.0540
_reflns_number_gt                2818
_reflns_number_total             4346
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2295.cif
_cod_data_source_block           I
_cod_original_cell_volume        1250.9(3)
_cod_database_code               2227041
_cod_database_fobs_code          2227041
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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 0.93894(6) 0.310770(17) 0.055477(9) 0.02449(6) Uani d . 1 . .
O O1 0.5216(4) 0.65997(11) 0.22190(6) 0.0219(4) Uani d . 1 . .
O O2 -0.9560(4) 0.35901(13) 0.51519(6) 0.0228(4) Uani d . 1 . .
N N1 0.1808(4) 0.51372(14) 0.27053(7) 0.0158(4) Uani d . 1 . .
N N2 -0.7439(4) 0.34661(14) 0.47039(7) 0.0165(4) Uani d . 1 . .
C C1 0.6150(5) 0.57912(16) 0.18617(8) 0.0156(5) Uani d . 1 . .
C C2 0.5081(5) 0.46983(15) 0.19213(8) 0.0150(5) Uani d . 1 . .
C C3 0.6111(5) 0.38957(16) 0.15310(8) 0.0174(5) Uani d . 1 . .
H H3 0.5429 0.3159 0.1565 0.021 Uiso calc R 1 . .
C C4 0.8098(5) 0.41758(17) 0.11007(9) 0.0181(5) Uani d . 1 . .
C C5 0.9174(5) 0.52501(16) 0.10466(8) 0.0174(4) Uani d . 1 . .
H H5 1.0571 0.5431 0.0751 0.021 Uiso calc R 1 . .
C C6 0.8195(5) 0.60434(17) 0.14244(9) 0.0189(5) Uani d . 1 . .
H H6 0.8922 0.6774 0.1387 0.023 Uiso calc R 1 . .
C C7 0.2943(5) 0.44092(17) 0.23670(9) 0.0172(5) Uani d . 1 . .
H H7 0.2362 0.3663 0.2411 0.021 Uiso calc R 1 . .
C C8 -0.0289(5) 0.48808(15) 0.31419(8) 0.0142(4) Uani d . 1 . .
C C9 -0.1308(5) 0.57570(17) 0.34784(9) 0.0181(5) Uani d . 1 . .
H H9 -0.0580 0.6477 0.3405 0.022 Uiso calc R 1 . .
C C10 -0.3373(5) 0.55866(17) 0.39193(9) 0.0185(5) Uani d . 1 . .
H H10 -0.4072 0.6195 0.4138 0.022 Uiso calc R 1 . .
C C11 -0.4435(5) 0.45385(15) 0.40458(8) 0.0154(4) Uani d . 1 . .
C C12 -0.3426(5) 0.36586(16) 0.37064(9) 0.0175(5) Uani d . 1 . .
H H12 -0.4139 0.2938 0.3783 0.021 Uiso calc R 1 . .
C C13 -0.1407(5) 0.38292(16) 0.32620(8) 0.0170(5) Uani d . 1 . .
H H13 -0.0766 0.3225 0.3034 0.020 Uiso calc R 1 . .
C C14 -0.6628(5) 0.44081(17) 0.45110(9) 0.0171(5) Uani d . 1 . .
H H14 -0.7489 0.5048 0.4678 0.021 Uiso calc R 1 . .
H H1 0.384(5) 0.6368(17) 0.2459(9) 0.022(7) Uiso d . 1 . .
H H2 -1.018(7) 0.302(2) 0.5186(12) 0.070(12) Uiso 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O1 H1 . . 111.7(14) ?
N2 O2 H2 . . 103(2) ?
C7 N1 C8 . . 122.91(18) ?
C14 N2 O2 . . 110.38(17) ?
O1 C1 C6 . . 118.97(18) ?
O1 C1 C2 . . 121.43(19) ?
C6 C1 C2 . . 119.60(18) ?
C3 C2 C1 . . 118.72(19) ?
C3 C2 C7 . . 120.18(18) ?
C1 C2 C7 . . 121.09(18) ?
C4 C3 C2 . . 120.14(19) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C3 C4 C5 . . 121.05(19) ?
C3 C4 Br1 . . 120.41(16) ?
C5 C4 Br1 . . 118.53(16) ?
C6 C5 C4 . . 119.5(2) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 120.93(19) ?
C5 C6 H6 . . 119.5 ?
C1 C6 H6 . . 119.5 ?
N1 C7 C2 . . 121.63(19) ?
N1 C7 H7 . . 119.2 ?
C2 C7 H7 . . 119.2 ?
C9 C8 C13 . . 118.23(19) ?
C9 C8 N1 . . 116.44(18) ?
C13 C8 N1 . . 125.33(18) ?
C10 C9 C8 . . 120.70(19) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 121.0(2) ?
C9 C10 H10 . . 119.5 ?
C11 C10 H10 . . 119.5 ?
C10 C11 C12 . . 118.3(2) ?
C10 C11 C14 . . 118.71(18) ?
C12 C11 C14 . . 122.92(18) ?
C13 C12 C11 . . 120.70(19) ?
C13 C12 H12 . . 119.7 ?
C11 C12 H12 . . 119.7 ?
C12 C13 C8 . . 120.99(19) ?
C12 C13 H13 . . 119.5 ?
C8 C13 H13 . . 119.5 ?
N2 C14 C11 . . 122.78(18) ?
N2 C14 H14 . . 118.6 ?
C11 C14 H14 . . 118.6 ?
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 C4 . 1.903(2) ?
O1 C1 . 1.352(2) ?
O1 H1 . 0.87(2) ?
O2 N2 . 1.409(2) ?
O2 H2 . 0.75(3) ?
N1 C7 . 1.286(2) ?
N1 C8 . 1.409(3) ?
N2 C14 . 1.283(2) ?
C1 C6 . 1.394(3) ?
C1 C2 . 1.419(3) ?
C2 C3 . 1.408(3) ?
C2 C7 . 1.445(3) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.398(3) ?
C5 C6 . 1.375(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
C8 C9 . 1.397(3) ?
C8 C13 . 1.401(3) ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.392(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.403(3) ?
C11 C14 . 1.460(3) ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
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
_geom_hbond_publ_flag
O1 H1 N1 . 0.87(2) 1.84(2) 2.593(2) 143(2) y
O2 H2 N2 2_456 0.75(3) 2.08(3) 2.830(2) 173(2) y
C5 H5 O2 4_564 0.95 2.54 3.463(3) 163 y
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
O1 C1 C2 C3 . . . . 179.22(19) ?
C6 C1 C2 C3 . . . . -0.5(3) ?
O1 C1 C2 C7 . . . . 0.1(3) ?
C6 C1 C2 C7 . . . . -179.5(2) ?
C1 C2 C3 C4 . . . . -0.3(3) ?
C7 C2 C3 C4 . . . . 178.75(19) ?
C2 C3 C4 C5 . . . . 1.0(3) ?
C2 C3 C4 Br1 . . . . -177.75(16) ?
C3 C4 C5 C6 . . . . -1.0(3) ?
Br1 C4 C5 C6 . . . . 177.87(17) ?
C4 C5 C6 C1 . . . . 0.1(3) ?
O1 C1 C6 C5 . . . . -179.1(2) ?
C2 C1 C6 C5 . . . . 0.5(3) ?
C8 N1 C7 C2 . . . . 179.75(19) ?
C3 C2 C7 N1 . . . . -175.3(2) ?
C1 C2 C7 N1 . . . . 3.8(3) ?
C7 N1 C8 C9 . . . . 179.5(2) ?
C7 N1 C8 C13 . . . . -0.4(3) ?
C13 C8 C9 C10 . . . . 0.0(3) ?
N1 C8 C9 C10 . . . . -179.95(19) ?
C8 C9 C10 C11 . . . . 1.3(3) ?
C9 C10 C11 C12 . . . . -1.6(3) ?
C9 C10 C11 C14 . . . . -179.44(19) ?
C10 C11 C12 C13 . . . . 0.6(3) ?
C14 C11 C12 C13 . . . . 178.34(19) ?
C11 C12 C13 C8 . . . . 0.7(3) ?
C9 C8 C13 C12 . . . . -1.0(3) ?
N1 C8 C13 C12 . . . . 178.95(19) ?
O2 N2 C14 C11 . . . . 179.74(18) ?
C10 C11 C14 N2 . . . . -171.1(2) ?
C12 C11 C14 N2 . . . . 11.2(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745520
