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#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/06/7120660.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.
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data_7120660
loop_
_publ_author_name
'Houjou, Hirohiko'
'Ikedo, Hana'
'Yoshikawa, Isao'
_publ_section_title
;
 Single-crystal UV-Vis spectroscopic examination of a striking odd-even
 effect on structure and chromic behaviour of salicylidene alkylamines
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06268K
_journal_year                    2017
_chemical_formula_moiety         'C14 H12 Br N O'
_chemical_formula_sum            'C14 H12 Br N O'
_chemical_formula_weight         290.16
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-08-03 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.290(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.730(6)
_cell_length_b                   6.093(2)
_cell_length_c                   14.524(7)
_cell_measurement_reflns_used    2223
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.90
_cell_volume                     1273.7(9)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8727
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.317
_diffrn_reflns_theta_min         2.871
_exptl_absorpt_coefficient_mu    3.210
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_description       plate
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol'
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0513
_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)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1380
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1189
_reflns_number_total             2299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7cc06268k2.cif
_cod_data_source_block           shelxl_CCDC5
_cod_database_code               7120660
_shelx_shelxl_version_number     2016/6
_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_min   0.436
_shelx_estimated_absorpt_t_max   0.910
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.1031(3) 0.7924(5) 0.1222(3) 0.0757(9) Uani 1 1 d . .
H1 H 0.146(4) 0.709(8) 0.152(4) 0.10(2) Uiso 1 1 d . .
C1 C 0.0219(3) 0.6806(7) 0.1117(3) 0.0569(11) Uani 1 1 d . .
C2 C -0.0592(4) 0.7796(7) 0.0646(3) 0.0629(12) Uani 1 1 d . .
H2 H -0.057050 0.920786 0.040823 0.075 Uiso 1 1 calc R U
C3 C -0.1431(4) 0.6716(8) 0.0524(3) 0.0674(13) Uani 1 1 d . .
H3 H -0.197207 0.739476 0.020302 0.081 Uiso 1 1 calc R U
C4 C -0.1465(3) 0.4621(8) 0.0879(3) 0.0668(12) Uani 1 1 d . .
C5 C -0.0668(3) 0.3604(7) 0.1358(3) 0.0611(12) Uani 1 1 d . .
H4 H -0.070220 0.220133 0.160187 0.073 Uiso 1 1 calc R U
C6 C 0.0192(3) 0.4666(6) 0.1482(2) 0.0523(11) Uani 1 1 d . .
Br1 Br -0.26124(4) 0.31218(11) 0.07020(5) 0.1142(4) Uani 1 1 d . .
C7 C 0.1036(4) 0.3523(8) 0.1949(3) 0.0674(13) Uani 1 1 d . .
H5 H 0.099338 0.209353 0.216032 0.081 Uiso 1 1 calc R U
N1 N 0.1828(3) 0.4438(7) 0.2075(2) 0.0753(11) Uani 1 1 d . .
C8 C 0.2638(4) 0.3127(9) 0.2544(4) 0.0977(18) Uani 1 1 d . .
H6 H 0.244289 0.163670 0.263527 0.117 Uiso 1 1 calc R U
H7 H 0.289769 0.374899 0.315890 0.117 Uiso 1 1 calc R U
C9 C 0.3365(3) 0.3100(8) 0.1962(3) 0.0652(12) Uani 1 1 d . .
C10 C 0.3986(4) 0.4787(9) 0.1969(4) 0.0858(16) Uani 1 1 d . .
H8 H 0.395534 0.600711 0.234599 0.103 Uiso 1 1 calc R U
C11 C 0.4652(4) 0.4718(11) 0.1432(5) 0.1023(19) Uani 1 1 d . .
H9 H 0.506281 0.588236 0.144743 0.123 Uiso 1 1 calc R U
C12 C 0.4706(4) 0.2960(12) 0.0883(5) 0.0983(17) Uani 1 1 d . .
H10 H 0.515789 0.290643 0.052337 0.118 Uiso 1 1 calc R U
C13 C 0.4105(4) 0.1276(10) 0.0857(4) 0.0936(16) Uani 1 1 d . .
H11 H 0.414008 0.007298 0.047176 0.112 Uiso 1 1 calc R U
C14 C 0.3439(4) 0.1325(8) 0.1396(4) 0.0777(14) Uani 1 1 d . .
H12 H 0.303549 0.014456 0.137633 0.093 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
C1 O1 H1 108(4)
O1 C1 C2 119.0(4)
O1 C1 C6 121.1(4)
C2 C1 C6 119.9(4)
C3 C2 C1 120.8(4)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 119.7(4)
C2 C3 H3 120.1
C4 C3 H3 120.1
C5 C4 C3 120.6(4)
C5 C4 Br1 119.5(4)
C3 C4 Br1 119.9(4)
C4 C5 C6 120.5(4)
C4 C5 H4 119.8
C6 C5 H4 119.8
C5 C6 C1 118.5(4)
C5 C6 C7 119.8(4)
C1 C6 C7 121.7(4)
N1 C7 C6 121.5(4)
N1 C7 H5 119.2
C6 C7 H5 119.2
C7 N1 C8 117.1(5)
N1 C8 C9 110.4(4)
N1 C8 H6 109.6
C9 C8 H6 109.6
N1 C8 H7 109.6
C9 C8 H7 109.6
H6 C8 H7 108.1
C10 C9 C14 117.0(5)
C10 C9 C8 122.8(5)
C14 C9 C8 120.2(5)
C9 C10 C11 121.7(5)
C9 C10 H8 119.2
C11 C10 H8 119.2
C12 C11 C10 119.9(5)
C12 C11 H9 120.1
C10 C11 H9 120.1
C11 C12 C13 120.0(6)
C11 C12 H10 120.0
C13 C12 H10 120.0
C12 C13 C14 120.6(5)
C12 C13 H11 119.7
C14 C13 H11 119.7
C9 C14 C13 120.8(5)
C9 C14 H12 119.6
C13 C14 H12 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.357(5)
O1 H1 0.86(5)
C1 C2 1.382(6)
C1 C6 1.411(5)
C2 C3 1.378(6)
C2 H2 0.9300
C3 C4 1.382(6)
C3 H3 0.9300
C4 C5 1.378(6)
C4 Br1 1.889(5)
C5 C6 1.400(6)
C5 H4 0.9300
C6 C7 1.461(6)
C7 N1 1.270(6)
C7 H5 0.9300
N1 C8 1.477(6)
C8 C9 1.499(7)
C8 H6 0.9700
C8 H7 0.9700
C9 C10 1.374(7)
C9 C14 1.377(7)
C10 C11 1.378(7)
C10 H8 0.9300
C11 C12 1.347(8)
C11 H9 0.9300
C12 C13 1.351(8)
C12 H10 0.9300
C13 C14 1.379(7)
C13 H11 0.9300
C14 H12 0.9300
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
O1 H1 N1 0.86(5) 1.84(5) 2.609(5) 149(5)
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
O1 C1 C2 C3 179.9(4)
C6 C1 C2 C3 -0.1(6)
C1 C2 C3 C4 0.2(6)
C2 C3 C4 C5 0.3(6)
C2 C3 C4 Br1 -179.4(3)
C3 C4 C5 C6 -0.9(6)
Br1 C4 C5 C6 178.7(3)
C4 C5 C6 C1 1.0(6)
C4 C5 C6 C7 -176.9(4)
O1 C1 C6 C5 179.5(3)
C2 C1 C6 C5 -0.5(5)
O1 C1 C6 C7 -2.7(6)
C2 C1 C6 C7 177.4(4)
C5 C6 C7 N1 -179.9(4)
C1 C6 C7 N1 2.3(6)
C6 C7 N1 C8 -179.2(4)
C7 N1 C8 C9 126.8(5)
N1 C8 C9 C10 81.3(6)
N1 C8 C9 C14 -99.4(5)
C14 C9 C10 C11 0.2(7)
C8 C9 C10 C11 179.6(5)
C9 C10 C11 C12 -0.2(8)
C10 C11 C12 C13 0.4(8)
C11 C12 C13 C14 -0.8(8)
C10 C9 C14 C13 -0.6(7)
C8 C9 C14 C13 -179.9(5)
C12 C13 C14 C9 0.9(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 681192
