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#$Date: 2020-07-04 04:34:08 +0300 (Sat, 04 Jul 2020) $
#$Revision: 253704 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/08/7240816.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_7240816
loop_
_publ_author_name
'Zhang, Zaixiang'
'SUZUKI, Masahiro'
'YANG, Yu'
'Yoshikawa, Isao'
'Yin, Qiuxiang'
'Houjou, Hirohiko'
_publ_section_title
;
 Seed-triggered solid-to-solid transformation between color polymorphs:
 Striking differences between quasi-isomorphous crystals of
 dichloro-substituted salicylideneaniline regioisomers
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00679C
_journal_year                    2020
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11
_chemical_melting_point          '417 (or phase transiiton to orange form)'
_chemical_name_common
N-(2-Hydroxy-4-chlorobenzylidene)-4-chloroaniline
_chemical_name_systematic        N-(4?-chlorosalicylidene)-4-chloroaniline
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2yc'
_space_group_name_H-M_alt        'I 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2020-05-05 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.26(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.140(5)
_cell_length_b                   6.848(6)
_cell_length_c                   27.39(2)
_cell_measurement_reflns_used    1729
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.00
_cell_volume                     1146.8(16)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            6509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_min         2.987
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_description       plate
_exptl_crystal_F_000             544
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         1298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0447
_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)+(0.0272P)²+2.8523P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1002
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1176
_reflns_number_total             1298
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00679c3.cif
_cod_data_source_block           4CC-y
_cod_original_sg_symbol_H-M      I2/c
_cod_database_code               7240816
_shelx_shelxl_version_number     2018/1
_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   0.854
_shelx_estimated_absorpt_t_max   0.984
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, 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
Cl1 Cl 0.30936(10) -0.05592(9) 0.03841(2) 0.02466(19) Uani 1 1 d . . . . .
C1 C 0.2019(4) -0.0232(3) 0.09436(7) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.3292(3) -0.0777(3) 0.13652(8) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.470391 -0.132277 0.134587 0.018 Uiso 1 1 calc R U . . .
C3 C 0.2474(3) -0.0514(3) 0.18155(8) 0.0156(4) Uani 1 1 d . . . . .
H2 H 0.333741 -0.086337 0.210814 0.023 Uiso 0.5 1 calc R U P A 2
O1 O 0.3856(5) -0.0804(4) 0.22299(11) 0.0169(6) Uani 0.5 1 d . . P B -1
H3 H 0.318053 -0.060319 0.247825 0.025 Uiso 0.5 1 calc R U P B -1
C4 C 0.0369(3) 0.0268(3) 0.18406(7) 0.0136(4) Uani 1 1 d . . . . .
C5 C -0.0875(3) 0.0788(3) 0.14070(8) 0.0136(4) Uani 1 1 d . . . . .
H4 H -0.230028 0.131071 0.142192 0.016 Uiso 1 1 calc R U . . .
C6 C -0.0060(4) 0.0551(3) 0.09570(8) 0.0163(4) Uani 1 1 d . . . . .
H5 H -0.090376 0.091614 0.066313 0.020 Uiso 1 1 calc R U . . .
C7 C -0.0504(14) 0.0534(12) 0.2310(3) 0.015(2) Uiso 0.5 1 d . . P C -1
H6 H -0.199129 0.090880 0.231605 0.018 Uiso 0.5 1 calc R U P C -1
N1 N 0.0656(11) 0.0282(9) 0.2716(2) 0.0121(18) Uiso 0.5 1 d . . P C -1
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C6 122.1(2) . . ?
C2 C1 Cl1 118.01(17) . . ?
C6 C1 Cl1 119.84(17) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H1 120.5 . . ?
C3 C2 H1 120.5 . . ?
O1 C3 C2 118.2(2) . . ?
O1 C3 C4 121.2(2) . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H2 119.9 . . ?
C4 C3 H2 119.9 . . ?
C3 O1 H3 109.5 . . ?
C5 C4 C3 119.24(19) . . ?
C5 C4 C7 120.3(4) . . ?
C3 C4 C7 120.5(4) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H4 119.6 . . ?
C4 C5 H4 119.6 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 H5 120.7 . . ?
C1 C6 H5 120.7 . . ?
N1 C7 C4 122.2(5) . . ?
N1 C7 H6 118.9 . . ?
C4 C7 H6 118.9 . . ?
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
Cl1 C1 1.738(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.385(3) . ?
C2 H1 0.9500 . ?
C3 O1 1.368(4) . ?
C3 C4 1.406(3) . ?
C3 H2 0.9500 . ?
O1 H3 0.8400 . ?
C4 C5 1.398(3) . ?
C4 C7 1.450(9) . ?
C5 C6 1.382(3) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 N1 1.275(6) . ?
C7 H6 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^a H3^a N1^a 0.84 1.84 2.582(7) 146.7 . 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
C6 C1 C2 C3 -0.7(3) . . . . ?
Cl1 C1 C2 C3 179.50(16) . . . . ?
C1 C2 C3 O1 -171.1(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
O1 C3 C4 C5 171.3(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
O1 C3 C4 C7 -8.6(5) . . . . ?
C2 C3 C4 C7 179.6(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C7 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
Cl1 C1 C6 C5 179.75(16) . . . . ?
C5 C4 C7 N1 -172.2(7) . . . . ?
C3 C4 C7 N1 7.8(10) . . . . ?
