#------------------------------------------------------------------------------
#$Date: 2019-11-17 09:26:29 +0200 (Sun, 17 Nov 2019) $
#$Revision: 229094 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/03/7230325.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_7230325
loop_
_publ_author_name
'Sugiyama, Haruki'
'Uekusa, Hidehiro'
_publ_section_title
;
 Relationship between crystal structures and photochromic properties of
 N-salicylideneaminopyridine derivatives
;
_journal_issue                   15
_journal_name_full               CrystEngComm
_journal_page_first              2144
_journal_paper_doi               10.1039/C8CE00003D
_journal_volume                  20
_journal_year                    2018
_chemical_compound_source        non-photochromic
_chemical_formula_moiety         'C12 H8 Br2 N2 O'
_chemical_formula_sum            'C12 H8 Br2 N2 O'
_chemical_formula_weight         356.02
_chemical_name_common            35Br-3SAP
_chemical_name_systematic        2,4-dibromo-6-[(E)-3-pyridyliminomethyl]phenol
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2017-12-30 deposited with the CCDC.
2018-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.499(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.6532(3)
_cell_length_b                   4.52630(10)
_cell_length_c                   18.6301(4)
_cell_measurement_reflns_used    11311
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.21
_cell_measurement_theta_min      3.76
_cell_volume                     1234.46(5)
_computing_cell_refinement       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        'PROCESS-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2008)'
_computing_publication_material  'SHELXL-2014/07 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12010
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.215
_diffrn_reflns_theta_min         3.759
_diffrn_source                   'rotating anode X-ray tube'
_exptl_absorpt_coefficient_mu    8.209
_exptl_absorpt_correction_T_max  0.532
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Absorption was corrected by ABSCOR'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate'
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0384
_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)+(0.0549P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1027
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1916
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce00003d2.cif
_cod_data_source_block           shelx_CCDC10
_cod_depositor_comments
'Adding full bibliography for 7230315--7230335.cif.'
_cod_database_code               7230325
_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   0.397
_shelx_estimated_absorpt_t_max   0.532
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br1 Br 0.70827(2) -0.41954(9) 0.36329(2) 0.05849(17) Uani 1 1 d . .
O1 O 0.55240(15) -0.0065(6) 0.39292(11) 0.0516(6) Uani 1 1 d . .
H1 H 0.518490 0.134705 0.398899 0.077 Uiso 1 1 calc R U
N1 N 0.41729(16) 0.3509(6) 0.35884(13) 0.0425(6) Uani 1 1 d . .
C1 C 0.55344(19) -0.0703(7) 0.32280(15) 0.0415(7) Uani 1 1 d . .
Br2 Br 0.55876(3) -0.33084(13) 0.07958(2) 0.0851(2) Uani 1 1 d . .
C2 C 0.6188(2) -0.2630(7) 0.29749(17) 0.0441(7) Uani 1 1 d . .
N3 N 0.22033(19) 0.8695(7) 0.35313(16) 0.0608(8) Uani 1 1 d . .
C3 C 0.6202(2) -0.3418(8) 0.22609(16) 0.0512(8) Uani 1 1 d . .
H3 H 0.663819 -0.474059 0.210635 0.061 Uiso 1 1 calc R U
C4 C 0.5563(2) -0.2222(8) 0.17765(17) 0.0528(8) Uani 1 1 d . .
C5 C 0.4923(2) -0.0239(8) 0.19945(16) 0.0500(8) Uani 1 1 d . .
H5 H 0.450437 0.057980 0.166136 0.060 Uiso 1 1 calc R U
C6 C 0.49017(19) 0.0552(7) 0.27247(15) 0.0417(7) Uani 1 1 d . .
C7 C 0.42379(19) 0.2729(7) 0.29346(16) 0.0437(7) Uani 1 1 d . .
H7 H 0.385001 0.357736 0.258399 0.052 Uiso 1 1 calc R U
C9 C 0.2824(2) 0.6724(8) 0.33349(18) 0.0546(8) Uani 1 1 d . .
H9 H 0.278794 0.604870 0.286301 0.066 Uiso 1 1 calc R U
C8 C 0.35200(18) 0.5616(7) 0.37880(15) 0.0399(6) Uani 1 1 d . .
C10 C 0.2259(2) 0.9608(8) 0.42125(18) 0.0526(8) Uani 1 1 d . .
H10 H 0.182795 1.095677 0.436203 0.063 Uiso 1 1 calc R U
C11 C 0.2919(2) 0.8663(8) 0.47034(17) 0.0543(8) Uani 1 1 d . .
H11 H 0.293510 0.937053 0.517243 0.065 Uiso 1 1 calc R U
C12 C 0.3559(2) 0.6649(7) 0.44918(16) 0.0490(8) Uani 1 1 d . .
H12 H 0.401370 0.598542 0.481676 0.059 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 109.5
C7 N1 C8 121.2(3)
O1 C1 C2 120.2(3)
O1 C1 C6 121.8(3)
C2 C1 C6 118.0(3)
C3 C2 C1 121.9(3)
C3 C2 Br1 119.2(2)
C1 C2 Br1 118.8(2)
C10 N3 C9 116.9(3)
C2 C3 C4 119.3(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C5 C4 C3 121.0(3)
C5 C4 Br2 119.8(3)
C3 C4 Br2 119.1(3)
C4 C5 C6 119.7(3)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 119.9(3)
C5 C6 C7 118.4(3)
C1 C6 C7 121.6(3)
N1 C7 C6 121.6(3)
N1 C7 H7 119.2
C6 C7 H7 119.2
N3 C9 C8 124.4(3)
N3 C9 H9 117.8
C8 C9 H9 117.8
C9 C8 C12 116.8(3)
C9 C8 N1 124.9(3)
C12 C8 N1 118.3(3)
N3 C10 C11 123.4(3)
N3 C10 H10 118.3
C11 C10 H10 118.3
C10 C11 C12 119.0(3)
C10 C11 H11 120.5
C12 C11 H11 120.5
C11 C12 C8 119.4(3)
C11 C12 H12 120.3
C8 C12 H12 120.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.893(3)
O1 C1 1.339(3)
O1 H1 0.8200
N1 C7 1.276(4)
N1 C8 1.412(4)
C1 C2 1.393(4)
C1 C6 1.409(4)
Br2 C4 1.894(3)
C2 C3 1.378(4)
N3 C10 1.334(4)
N3 C9 1.337(4)
C3 C4 1.383(5)
C3 H3 0.9300
C4 C5 1.372(5)
C5 C6 1.408(4)
C5 H5 0.9300
C6 C7 1.450(4)
C7 H7 0.9300
C9 C8 1.389(4)
C9 H9 0.9300
C8 C12 1.391(4)
C10 C11 1.370(4)
C10 H10 0.9300
C11 C12 1.378(4)
C11 H11 0.9300
C12 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
_geom_hbond_site_symmetry_A
O1 H1 N1 0.82 1.90 2.613(3) 144.5 .
C3 H3 Br1 0.93 3.11 4.036(3) 171.1 2_645
C7 H7 N3 0.93 2.53 3.407(4) 156.4 2_545
C11 H11 Br1 0.93 3.12 3.985(3) 155.6 3_666
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 177.8(3)
C6 C1 C2 C3 -2.8(4)
O1 C1 C2 Br1 -2.4(4)
C6 C1 C2 Br1 177.0(2)
C1 C2 C3 C4 1.3(5)
Br1 C2 C3 C4 -178.5(2)
C2 C3 C4 C5 0.8(5)
C2 C3 C4 Br2 179.9(2)
C3 C4 C5 C6 -1.3(5)
Br2 C4 C5 C6 179.6(2)
C4 C5 C6 C1 -0.2(5)
C4 C5 C6 C7 177.9(3)
O1 C1 C6 C5 -178.4(3)
C2 C1 C6 C5 2.3(4)
O1 C1 C6 C7 3.5(4)
C2 C1 C6 C7 -175.8(3)
C8 N1 C7 C6 -179.6(3)
C5 C6 C7 N1 178.9(3)
C1 C6 C7 N1 -3.0(4)
C10 N3 C9 C8 -0.8(6)
N3 C9 C8 C12 0.2(5)
N3 C9 C8 N1 179.2(3)
C7 N1 C8 C9 9.0(5)
C7 N1 C8 C12 -172.0(3)
C9 N3 C10 C11 1.0(5)
N3 C10 C11 C12 -0.5(5)
C10 C11 C12 C8 -0.2(5)
C9 C8 C12 C11 0.3(5)
N1 C8 C12 C11 -178.8(3)
