#------------------------------------------------------------------------------
#$Date: 2023-01-05 14:18:08 +0200 (Thu, 05 Jan 2023) $
#$Revision: 280124 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062194.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_7062194
loop_
_publ_author_name
'Hulushe, Siya T.'
'Malan, Frederick P.'
'Hosten, Eric C.'
'Lobb, Kevin A.'
'Khanye, Setshaba D.'
'Watkins, Gareth M.'
_publ_section_title
;
 Photo-and thermoresponsive N-salicylideneaniline derivatives: solid-state
 studies and structural aspects
;
_journal_issue                   43
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20940
_journal_page_last               20950
_journal_paper_doi               10.1039/D1NJ03056F
_journal_volume                  46
_journal_year                    2022
_chemical_compound_source        Synthsized
_chemical_formula_moiety         'C13 H9 Br N2 O3'
_chemical_formula_sum            'C13 H9 Br N2 O3'
_chemical_formula_weight         321.13
_chemical_melting_point          471
_chemical_name_common
2-((E)-(2-bromophenylimino)methyl)-4-nitrophenol
_chemical_name_systematic
2-((E)-(2-bromophenylimino)methyl)-4-nitrophenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_audit_creation_date             2021-02-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2021-03-25 deposited with the CCDC.	2022-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.651(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.4282(9)
_cell_length_b                   11.5053(14)
_cell_length_c                   14.0071(16)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.69
_cell_volume                     1194.7(2)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.9887
_diffrn_measured_fraction_theta_max 0.9887
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37547
_diffrn_reflns_theta_full        28.3791
_diffrn_reflns_theta_max         28.38
_diffrn_reflns_theta_min         2.29
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.446
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.7853
_exptl_crystal_description       block
_exptl_crystal_F_000             639.2017
_exptl_crystal_preparation       'Mechanochemical synthesis'
_exptl_crystal_recrystallization_method
'Recrystallization by slow evaporation in solution of ethyl acetate/methanol'
_exptl_crystal_size_max          0.716
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.5153
_refine_diff_density_min         -0.2885
_refine_diff_density_rms         0.0625
_refine_ls_d_res_high            0.7477
_refine_ls_d_res_low             8.8833
_refine_ls_goodness_of_fit_ref   1.0598
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2964
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0598
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0236P)²+0.6243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0518
_reflns_Friedel_coverage         0.000
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2700
_reflns_number_total             2964
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj03056f2.cif
_cod_data_source_block           ka076c_c_a
_cod_original_cell_volume        1194.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7062194
_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.
;
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_refinement_flags_posn
Br1 Br 0.91077(2) 0.396017(13) 0.760327(10) 0.02804(6) Uani 1.000000 .
O1 O 0.88969(15) 0.64451(10) 0.59478(7) 0.0266(2) Uani 1.000000 .
O2 O 0.57969(16) 0.88580(10) 0.22193(9) 0.0348(3) Uani 1.000000 .
O3 O 0.54822(18) 0.70560(12) 0.18054(8) 0.0401(3) Uani 1.000000 .
N1 N 0.78469(15) 0.43371(10) 0.55232(8) 0.0205(2) Uani 1.000000 .
N2 N 0.59358(16) 0.78122(12) 0.23852(9) 0.0267(3) Uani 1.000000 .
C11 C 0.72717(18) 0.59349(11) 0.44710(10) 0.0193(3) Uani 1.000000 .
C16 C 0.65455(19) 0.63020(12) 0.35783(10) 0.0217(3) Uani 1.000000 .
H16 H 0.59777(19) 0.57730(12) 0.31571(10) 0.0260(3) Uiso 1.000000 R
C22 C 0.82530(18) 0.28253(12) 0.67133(10) 0.0207(3) Uani 1.000000 .
C15 C 0.66764(18) 0.74522(12) 0.33269(10) 0.0219(3) Uani 1.000000 .
C21 C 0.77228(18) 0.31551(12) 0.57740(10) 0.0203(3) Uani 1.000000 .
C12 C 0.81333(18) 0.67549(12) 0.50973(10) 0.0208(3) Uani 1.000000 .
C13 C 0.8205(2) 0.79269(13) 0.48295(10) 0.0248(3) Uani 1.000000 .
H13 H 0.8741(2) 0.84705(13) 0.52488(10) 0.0298(3) Uiso 1.000000 R
C14 C 0.74810(19) 0.82734(13) 0.39452(10) 0.0244(3) Uani 1.000000 .
H14 H 0.75300(19) 0.90495(13) 0.37632(10) 0.0293(3) Uiso 1.000000 R
C1 C 0.71249(18) 0.47216(12) 0.47298(9) 0.0209(3) Uani 1.000000 .
H1a H 0.64966(18) 0.42133(12) 0.43137(9) 0.0251(3) Uiso 1.000000 R
C23 C 0.8173(2) 0.16797(13) 0.70112(10) 0.0254(3) Uani 1.000000 .
H23 H 0.8544(2) 0.14781(13) 0.76360(10) 0.0304(3) Uiso 1.000000 R
C26 C 0.7133(2) 0.22803(13) 0.51356(11) 0.0259(3) Uani 1.000000 .
H26 H 0.6809(2) 0.24700(13) 0.45025(11) 0.0310(3) Uiso 1.000000 R
C25 C 0.7024(2) 0.11380(13) 0.54314(12) 0.0286(3) Uani 1.000000 .
H25 H 0.6607(2) 0.05698(13) 0.49998(12) 0.0344(4) Uiso 1.000000 R
C24 C 0.7532(2) 0.08344(13) 0.63672(12) 0.0282(3) Uani 1.000000 .
H24 H 0.7445(2) 0.00656(13) 0.65642(12) 0.0338(4) Uiso 1.000000 R
H1 H 0.877(3) 0.577(2) 0.6009(19) 0.059(8) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
H1 O1 C12 108.2(19) . . ?
C1 N1 C21 121.26(12) . . ?
O3 N2 O2 123.71(13) . . ?
C15 N2 O2 118.17(13) . . ?
C15 N2 O3 118.12(13) . . ?
C12 C11 C16 119.21(13) . . ?
C1 C11 C16 119.02(12) . . ?
C1 C11 C12 121.76(12) . . ?
H16 C16 C11 120.28(8) . . ?
C15 C16 C11 119.44(13) . . ?
C15 C16 H16 120.28(8) . . ?
C21 C22 Br1 119.70(10) . . ?
C23 C22 Br1 118.59(10) . . ?
C23 C22 C21 121.71(13) . . ?
C16 C15 N2 118.49(13) . . ?
C14 C15 N2 119.56(13) . . ?
C14 C15 C16 121.95(13) . . ?
C22 C21 N1 118.45(12) . . ?
C26 C21 N1 123.93(12) . . ?
C26 C21 C22 117.61(13) . . ?
C11 C12 O1 121.71(13) . . ?
C13 C12 O1 118.33(13) . . ?
C13 C12 C11 119.96(13) . . ?
H13 C13 C12 120.00(8) . . ?
C14 C13 C12 119.99(13) . . ?
C14 C13 H13 120.00(9) . . ?
C13 C14 C15 119.40(13) . . ?
H14 C14 C15 120.30(8) . . ?
H14 C14 C13 120.30(9) . . ?
C11 C1 N1 121.05(13) . . ?
H1a C1 N1 119.47(8) . . ?
H1a C1 C11 119.47(8) . . ?
H23 C23 C22 120.33(8) . . ?
C24 C23 C22 119.34(13) . . ?
C24 C23 H23 120.33(9) . . ?
H26 C26 C21 119.50(8) . . ?
C25 C26 C21 120.99(14) . . ?
C25 C26 H26 119.50(9) . . ?
H25 C25 C26 119.81(9) . . ?
C24 C25 C26 120.38(14) . . ?
C24 C25 H25 119.81(9) . . ?
C25 C24 C23 119.94(14) . . ?
H24 C24 C23 120.03(9) . . ?
H24 C24 C25 120.03(9) . . ?
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 C22 1.8871(14) . ?
O1 C12 1.3349(16) . ?
O1 H1 0.79(3) . ?
O2 N2 1.2286(18) . ?
O3 N2 1.2228(18) . ?
N1 C21 1.4090(18) . ?
N1 C1 1.2816(17) . ?
N2 C15 1.4566(17) . ?
C11 C16 1.3954(18) . ?
C11 C12 1.4134(19) . ?
C11 C1 1.4481(19) . ?
C16 H16 0.9300 . ?
C16 C15 1.374(2) . ?
C22 C21 1.4016(18) . ?
C22 C23 1.385(2) . ?
C15 C14 1.391(2) . ?
C21 C26 1.398(2) . ?
C12 C13 1.402(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(2) . ?
C14 H14 0.9300 . ?
C1 H1a 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.390(2) . ?
C26 H26 0.9300 . ?
C26 C25 1.382(2) . ?
C25 H25 0.9300 . ?
C25 C24 1.386(2) . ?
C24 H24 0.9300 . ?
