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#$Date: 2023-10-06 03:05:04 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247235.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_7247235
loop_
_publ_author_name
'Yoshikawa, Isao'
'Zhang, Zaixiang'
'Suzuki, Masahiro'
'Ikedo, Hana'
'Yin, Qiuxiang'
'Houjou, Hirohiko'
_publ_section_title
;
 Active control of molecular stacking types in a congeneric library of
 dihalogenated salicylideneaniline crystals and their solid solutions
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5109
_journal_page_last               5117
_journal_paper_doi               10.1039/D3CE00601H
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C13 H9 Br2 N O'
_chemical_formula_sum            'C13 H9 Br2 N O'
_chemical_formula_weight         355.03
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2023-08-02 deposited with the CCDC.	2023-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   56.4542(12)
_cell_length_b                   6.9020(2)
_cell_length_c                   6.10530(10)
_cell_measurement_reflns_used    19223
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      29.2300
_cell_measurement_theta_min      2.8710
_cell_volume                     2378.91(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.107a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_publication_material  'Yadokari-XG (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 5.811
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       74
_diffrn_reflns_limit_h_min       -74
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            25290
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.152
_diffrn_reflns_theta_min         2.887
_diffrn_source                   'rotating anode X-ray generator'
_exptl_absorpt_coefficient_mu    6.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.983
_exptl_crystal_description       prism
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane and dichloromethane'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.837
_refine_diff_density_rms         0.174
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0391
_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)+(0.0407P)²+7.1408P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2882
_reflns_number_total             3138
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00601h2.cif
_cod_data_source_block           5BB
_cod_depositor_comments
'Adding full bibliography for 7247230--7247235.cif.'
_cod_database_code               7247235
_shelx_shelxl_version_number     2019/3
_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   0.281
_shelx_estimated_absorpt_t_max   0.391
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10902(4) 0.5709(3) 1.2312(4) 0.0153(5) Uani 1 1 d . . . . .
H1 H 0.121204 0.552860 1.154945 0.023 Uiso 1 1 calc R U . . .
C1 C 0.08947(5) 0.5363(4) 1.1081(5) 0.0108(6) Uani 1 1 d . . . . .
C2 C 0.06724(5) 0.5745(4) 1.1965(5) 0.0120(6) Uani 1 1 d . . . . .
H2 H 0.065997 0.624258 1.341104 0.014 Uiso 1 1 calc R U . . .
C3 C 0.04686(5) 0.5407(4) 1.0752(5) 0.0128(6) Uani 1 1 d . . . . .
H3 H 0.031711 0.566922 1.136138 0.015 Uiso 1 1 calc R U . . .
C4 C 0.04886(5) 0.4681(4) 0.8641(5) 0.0108(5) Uani 1 1 d . . . . .
C5 C 0.07066(5) 0.4287(4) 0.7717(5) 0.0106(6) Uani 1 1 d . . . . .
H4 H 0.071613 0.377437 0.627556 0.013 Uiso 1 1 calc R U . . .
C6 C 0.09145(5) 0.4650(4) 0.8919(5) 0.0101(5) Uani 1 1 d . . . . .
Br1 Br 0.02103(2) 0.42922(5) 0.69376(5) 0.01552(10) Uani 1 1 d . . . . .
C7 C 0.11432(5) 0.4431(4) 0.7851(5) 0.0104(6) Uani 1 1 d . . . . .
H5 H 0.114971 0.405627 0.635461 0.012 Uiso 1 1 calc R U . . .
N1 N 0.13378(4) 0.4740(4) 0.8911(4) 0.0114(5) Uani 1 1 d . . . . .
C8 C 0.15557(5) 0.4823(4) 0.7764(5) 0.0101(5) Uani 1 1 d . . . . .
C9 C 0.15725(5) 0.5631(4) 0.5665(5) 0.0118(6) Uani 1 1 d . . . . .
H6 H 0.143359 0.606769 0.493861 0.014 Uiso 1 1 calc R U . . .
C10 C 0.17924(5) 0.5798(4) 0.4637(5) 0.0126(6) Uani 1 1 d . . . . .
H7 H 0.180436 0.634052 0.321103 0.015 Uiso 1 1 calc R U . . .
C11 C 0.19934(5) 0.5157(5) 0.5732(5) 0.0130(6) Uani 1 1 d . . . . .
C12 C 0.19816(5) 0.4383(4) 0.7824(5) 0.0132(6) Uani 1 1 d . . . . .
H8 H 0.212150 0.397084 0.855212 0.016 Uiso 1 1 calc R U . . .
C13 C 0.17620(5) 0.4216(4) 0.8844(5) 0.0111(5) Uani 1 1 d . . . . .
H9 H 0.175182 0.368908 1.027797 0.013 Uiso 1 1 calc R U . . .
Br2 Br 0.22902(2) 0.53870(5) 0.42882(6) 0.01911(11) Uani 1 1 d . . . . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 121.0(3) . . ?
C2 C1 C6 120.0(3) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 Br1 119.0(2) . . ?
C3 C4 Br1 119.4(2) . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H4 120.1 . . ?
C6 C5 H4 120.1 . . ?
C5 C6 C1 118.9(3) . . ?
C5 C6 C7 119.2(3) . . ?
C1 C6 C7 121.7(3) . . ?
N1 C7 C6 120.8(3) . . ?
N1 C7 H5 119.6 . . ?
C6 C7 H5 119.6 . . ?
C7 N1 C8 119.8(3) . . ?
C9 C8 C13 119.5(3) . . ?
C9 C8 N1 121.8(3) . . ?
C13 C8 N1 118.5(3) . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H6 119.8 . . ?
C8 C9 H6 119.8 . . ?
C11 C10 C9 118.9(3) . . ?
C11 C10 H7 120.5 . . ?
C9 C10 H7 120.5 . . ?
C12 C11 C10 121.8(3) . . ?
C12 C11 Br2 120.1(2) . . ?
C10 C11 Br2 118.1(2) . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H8 120.4 . . ?
C13 C12 H8 120.4 . . ?
C12 C13 C8 120.3(3) . . ?
C12 C13 H9 119.8 . . ?
C8 C13 H9 119.8 . . ?
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
O1 C1 1.356(4) . ?
O1 H1 0.8400 . ?
C1 C2 1.392(4) . ?
C1 C6 1.413(4) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(4) . ?
C4 Br1 1.903(3) . ?
C5 C6 1.407(4) . ?
C5 H4 0.9500 . ?
C6 C7 1.455(4) . ?
C7 N1 1.293(4) . ?
C7 H5 0.9500 . ?
N1 C8 1.416(4) . ?
C8 C9 1.400(4) . ?
C8 C13 1.402(4) . ?
C9 C10 1.396(4) . ?
C9 H6 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H7 0.9500 . ?
C11 C12 1.386(5) . ?
C11 Br2 1.900(3) . ?
C12 C13 1.392(4) . ?
C12 H8 0.9500 . ?
C13 H9 0.9500 . ?
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
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.84 1.84 2.591(4) 147.5 . yes
C9 H6 O1 0.95 2.53 3.407(4) 153.9 1_554 yes
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
_geom_torsion_publ_flag
O1 C1 C2 C3 -180.0(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C1 C2 C3 C4 0.0(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 Br1 -178.0(2) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
Br1 C4 C5 C6 177.1(2) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 C7 -173.4(3) . . . . ?
O1 C1 C6 C5 179.1(3) . . . . ?
C2 C1 C6 C5 -1.8(4) . . . . ?
O1 C1 C6 C7 -5.9(4) . . . . ?
C2 C1 C6 C7 173.2(3) . . . . ?
C5 C6 C7 N1 -179.5(3) . . . . ?
C1 C6 C7 N1 5.5(4) . . . . ?
C6 C7 N1 C8 -169.9(3) . . . . ?
C7 N1 C8 C9 36.0(4) . . . . ?
C7 N1 C8 C13 -149.2(3) . . . . ?
C13 C8 C9 C10 1.2(5) . . . . ?
N1 C8 C9 C10 176.1(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C9 C10 C11 Br2 179.6(2) . . . . ?
C10 C11 C12 C13 0.9(5) . . . . ?
Br2 C11 C12 C13 -179.6(2) . . . . ?
C11 C12 C13 C8 0.1(5) . . . . ?
C9 C8 C13 C12 -1.1(5) . . . . ?
N1 C8 C13 C12 -176.1(3) . . . . ?
