#------------------------------------------------------------------------------
#$Date: 2022-03-21 11:16:05 +0200 (Mon, 21 Mar 2022) $
#$Revision: 273867 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/48/8104819.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_8104819
loop_
_publ_author_name
'Xu, Xindi'
'Ma, Xun'
'Huang, Meifen'
'Li, Tianyu'
'Wu, Qiong'
_publ_section_title
;
 Crystal structure of
 4-bromo-N′-[(3-bromo-2-hydroxyphenyl)methylidene]benzohydrazide
 methanol solvate, C15H14Br2N2O3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              323
_journal_page_last               324
_journal_paper_doi               10.1515/ncrs-2020-0540
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C14 H10 Br2 N2 O2, C H4 O'
_chemical_formula_sum            'C15 H14 Br2 N2 O3'
_chemical_formula_weight         430.10
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                99.458(2)
_cell_angle_beta                 100.401(2)
_cell_angle_gamma                99.499(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2748(3)
_cell_length_b                   9.0786(4)
_cell_length_c                   12.8613(5)
_cell_measurement_reflns_used    5335
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.15
_cell_measurement_theta_min      2.56
_cell_volume                     807.35(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0360
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.447
_diffrn_reflns_theta_min         2.321
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.033
_exptl_absorpt_correction_T_max  0.0276
_exptl_absorpt_correction_T_min  0.0085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0988 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.3080.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_F_000             424
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0334P)²+0.1877P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0673
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2746
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2020-0540_suppl.cif
_cod_data_source_block           X3
_cod_database_code               8104819
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), N2(H2A), C8(H8), C2(H2B), C5(H5), C14(H14), C3(H3), C6(H6), C12(H12)
2.b Idealised Me refined as rotating group:
 C3AA(H3AA,H3AB,H3AC)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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 0.10184(4) 0.49086(3) 0.77333(2) 0.04662(10) Uani 1 1 d . . . . .
Br2 Br 0.34294(4) 1.34147(3) 0.03626(2) 0.05154(10) Uani 1 1 d . . . . .
C1 C 0.1306(3) 0.7890(3) 0.51219(19) 0.0344(5) Uani 1 1 d . . . . .
C2 C 0.2973(4) 0.7758(3) 0.5805(2) 0.0381(5) Uani 1 1 d . . . . .
H2B H 0.4176 0.8273 0.5733 0.046 Uiso 1 1 calc R . . . .
C3AA C 0.4688(5) 0.6853(4) 0.2888(3) 0.0709(10) Uani 1 1 d . . . . .
H3AA H 0.5272 0.6428 0.2307 0.106 Uiso 1 1 calc GR . . . .
H3AB H 0.3538 0.7194 0.2576 0.106 Uiso 1 1 calc GR . . . .
H3AC H 0.4345 0.6070 0.3299 0.106 Uiso 1 1 calc GR . . . .
C3 C 0.2883(4) 0.6879(3) 0.6589(2) 0.0397(6) Uani 1 1 d . . . . .
H3 H 0.4016 0.6791 0.7055 0.048 Uiso 1 1 calc R . . . .
C4 C 0.1129(4) 0.6138(3) 0.66817(19) 0.0365(5) Uani 1 1 d . . . . .
C5 C -0.0543(4) 0.6275(3) 0.6030(2) 0.0385(5) Uani 1 1 d . . . . .
H5 H -0.1742 0.5770 0.6116 0.046 Uiso 1 1 calc R . . . .
C6 C -0.0449(4) 0.7156(3) 0.52495(19) 0.0354(5) Uani 1 1 d . . . . .
H6 H -0.1590 0.7259 0.4800 0.043 Uiso 1 1 calc R . . . .
C7 C 0.1553(4) 0.8851(3) 0.42971(19) 0.0342(5) Uani 1 1 d . . . . .
C8 C -0.1239(3) 1.0016(3) 0.22009(18) 0.0340(5) Uani 1 1 d . . . . .
H8 H -0.2486 0.9570 0.2254 0.041 Uiso 1 1 calc R . . . .
C9 C -0.0972(4) 1.0896(3) 0.13783(19) 0.0343(5) Uani 1 1 d . . . . .
C10 C 0.0854(3) 1.1611(3) 0.12888(19) 0.0355(5) Uani 1 1 d . . . . .
C11 C 0.0982(4) 1.2425(3) 0.0477(2) 0.0377(5) Uani 1 1 d . . . . .
C12 C -0.0614(4) 1.2551(3) -0.0248(2) 0.0434(6) Uani 1 1 d . . . . .
H12 H -0.0481 1.3104 -0.0805 0.052 Uiso 1 1 calc R . . . .
C13 C -0.2398(4) 1.1867(3) -0.0154(2) 0.0446(6) Uani 1 1 d . . . . .
H13 H -0.3503 1.1949 -0.0644 0.054 Uiso 1 1 calc R . . . .
C14 C -0.2570(4) 1.1065(3) 0.0655(2) 0.0393(6) Uani 1 1 d . . . . .
H14 H -0.3806 1.0614 0.0723 0.047 Uiso 1 1 calc R . . . .
N1 N 0.0224(3) 0.9845(2) 0.28554(15) 0.0335(4) Uani 1 1 d . . . . .
N2 N -0.0056(3) 0.9018(2) 0.36357(15) 0.0332(4) Uani 1 1 d . . . . .
H2A H -0.1204 0.8620 0.3705 0.040 Uiso 1 1 calc R . . . .
O1 O 0.3128(3) 0.9463(2) 0.42131(15) 0.0433(4) Uani 1 1 d . . . . .
O2 O 0.2476(2) 1.1526(2) 0.19744(14) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.2191 1.1033 0.2441 0.061 Uiso 1 1 calc GR . . . .
O3 O 0.5985(3) 0.8092(2) 0.35738(16) 0.0491(5) Uani 1 1 d . . . . .
H3A H 0.5388 0.8665 0.3902 0.074 Uiso 1 1 calc GR . . . .
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
C14 C13 C12 119.7(2) . .
C7 N2 N1 116.0(2) . .
O1 C7 N2 120.9(2) . .
O1 C7 C1 121.7(2) . .
N2 C7 C1 117.5(2) . .
C10 C9 C8 122.1(2) . .
C14 C9 C8 119.3(2) . .
C14 C9 C10 118.6(2) . .
N1 C8 C9 119.3(2) . .
C8 N1 N2 118.5(2) . .
O2 C10 C9 122.2(2) . .
O2 C10 C11 119.4(2) . .
C11 C10 C9 118.4(2) . .
C3 C2 C1 120.5(2) . .
C4 C5 C6 119.2(2) . .
C2 C1 C7 116.5(2) . .
C6 C1 C7 124.2(2) . .
C6 C1 C2 119.2(2) . .
C10 C11 Br2 118.72(19) . .
C10 C11 C12 122.1(2) . .
C12 C11 Br2 119.15(19) . .
C13 C14 C9 121.7(2) . .
C5 C4 Br1 119.57(19) . .
C3 C4 Br1 118.77(19) . .
C3 C4 C5 121.7(2) . .
C4 C3 C2 118.9(2) . .
C5 C6 C1 120.4(2) . .
C13 C12 C11 119.5(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C4 1.894(2) .
Br2 C11 1.899(3) .
O1 C7 1.220(3) .
O2 C10 1.361(3) .
O3 C3AA 1.399(4) .
C13 C14 1.376(4) .
C13 C12 1.378(4) .
N2 C7 1.363(3) .
N2 N1 1.372(3) .
C7 C1 1.496(3) .
C9 C8 1.448(3) .
C9 C10 1.412(3) .
C9 C14 1.399(4) .
C8 N1 1.280(3) .
C10 C11 1.383(3) .
C2 C1 1.398(3) .
C2 C3 1.389(3) .
C5 C4 1.383(4) .
C5 C6 1.387(3) .
C1 C6 1.390(3) .
C11 C12 1.385(4) .
C4 C3 1.376(4) .
