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#$Date: 2022-03-22 11:16:26 +0200 (Tue, 22 Mar 2022) $
#$Revision: 273890 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104827.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_8104827
loop_
_publ_author_name
'Xu, Xindi'
'Tian, Hui'
'Wang, Xia'
'Wang, Man'
'Wu, Qiong'
_publ_section_title
;
 Crystal structure of
 4-bromo-N′-[(3-chloro-2-hydroxyphenyl)methylidene]benzohydrazide,
 C14H7Br2N2O2
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              347
_journal_page_last               348
_journal_paper_doi               10.1515/ncrs-2020-0586
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H7 Br2 N2 O2'
_chemical_formula_sum            'C14 H10 Br2 N2 O2'
_chemical_formula_weight         398.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 91.0784(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8308(2)
_cell_length_b                   6.1438(2)
_cell_length_c                   23.0836(9)
_cell_measurement_reflns_used    3064
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      3.53
_cell_volume                     684.99(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7475
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.432
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.919
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0087
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0929 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.3152.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_description       needle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.105
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+4.5954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1256
_reflns_number_total             1392
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0586_suppl.cif
_cod_data_source_block           mo_1022_2_0m
_cod_database_code               8104827
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.416
_shelx_estimated_absorpt_t_min   0.384
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: O1(0.5) H1(0.5) O2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C3(H3)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.19186(15) 0.44226(11) 0.29563(3) 0.0497(2) Uani 1 1 d . . . . .
O1 O 0.3352(16) -0.0676(15) 0.4698(3) 0.0398(19) Uani 0.5 1 d . . P . .
H1 H 0.259304 -0.160050 0.491143 0.060 Uiso 0.5 1 calc R U P . .
O2 O -0.3915(17) -0.3968(13) 0.4479(4) 0.042(2) Uani 0.5 1 d . . P . .
N1 N 0.0380(10) -0.4121(8) 0.4838(2) 0.0395(12) Uani 1 1 d . . . . .
C2 C 0.1643(12) -0.0134(10) 0.4274(3) 0.0401(14) Uani 1 1 d . . . . .
C6 C -0.2070(12) -0.1013(10) 0.3593(3) 0.0428(15) Uani 1 1 d . . . . .
H6 H -0.357737 -0.191717 0.347766 0.051 Uiso 1 1 calc R U . . .
C1 C -0.0621(12) -0.1478(10) 0.4104(3) 0.0369(13) Uani 1 1 d . . . . .
C4 C 0.0867(12) 0.2048(10) 0.3430(3) 0.0378(13) Uani 1 1 d . . . . .
C7 C -0.1447(13) -0.3393(11) 0.4451(3) 0.0439(15) Uani 1 1 d . . . . .
C5 C -0.1371(12) 0.0729(11) 0.3250(3) 0.0418(14) Uani 1 1 d . . . . .
H5 H -0.237255 0.103173 0.290092 0.050 Uiso 1 1 calc R U . . .
C3 C 0.2328(12) 0.1653(10) 0.3933(3) 0.0390(13) Uani 1 1 d . . . . .
H3 H 0.379983 0.259160 0.404846 0.047 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
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
C2 O1 H1 109.5 . .
C7 N1 N1 117.0(6) . 3_546
O1 C2 C1 122.0(6) . .
O1 C2 C3 118.0(6) . .
C3 C2 C1 119.4(6) . .
C1 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C5 C6 C1 121.5(6) . .
C2 C1 C7 121.7(5) . .
C6 C1 C2 119.2(6) . .
C6 C1 C7 119.0(5) . .
C5 C4 Br1 119.0(5) . .
C3 C4 Br1 119.0(5) . .
C3 C4 C5 122.0(6) . .
O2 C7 N1 119.7(7) . .
O2 C7 C1 121.4(7) . .
N1 C7 C1 116.8(5) . .
C6 C5 C4 118.2(6) . .
C6 C5 H5 120.9 . .
C4 C5 H5 120.9 . .
C2 C3 H3 120.2 . .
C4 C3 C2 119.7(6) . .
C4 C3 H3 120.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.898(6) .
O1 H1 0.8400 .
O1 C2 1.312(9) .
O2 C7 1.246(10) .
N1 N1 1.368(10) 3_546
N1 C7 1.322(8) .
C2 C1 1.420(8) .
C2 C3 1.395(8) .
C6 H6 0.9500 .
C6 C1 1.390(8) .
C6 C5 1.377(9) .
C1 C7 1.482(8) .
C4 C5 1.408(8) .
C4 C3 1.368(8) .
C5 H5 0.9500 .
C3 H3 0.9500 .
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
Br1 C4 C5 C6 178.7(4) . . . .
Br1 C4 C3 C2 -177.6(4) . . . .
O1 C2 C1 C6 -169.1(7) . . . .
O1 C2 C1 C7 9.6(10) . . . .
O1 C2 C3 C4 168.9(7) . . . .
N1 N1 C7 O2 15.9(11) 3_546 . . .
N1 N1 C7 C1 179.6(6) 3_546 . . .
C2 C1 C7 O2 147.0(7) . . . .
C2 C1 C7 N1 -16.4(9) . . . .
C6 C1 C7 O2 -34.3(10) . . . .
C6 C1 C7 N1 162.3(6) . . . .
C1 C2 C3 C4 -2.1(9) . . . .
C1 C6 C5 C4 -0.1(9) . . . .
C5 C6 C1 C2 -0.4(9) . . . .
C5 C6 C1 C7 -179.1(6) . . . .
C5 C4 C3 C2 1.6(9) . . . .
C3 C2 C1 C6 1.5(9) . . . .
C3 C2 C1 C7 -179.8(6) . . . .
C3 C4 C5 C6 -0.5(9) . . . .
