#------------------------------------------------------------------------------
#$Date: 2019-11-28 18:41:39 +0200 (Thu, 28 Nov 2019) $
#$Revision: 244319 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/87/7238729.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_7238729
loop_
_publ_author_name
'Safin, Damir A.'
'Robeyns, Koen'
'Garcia, Yann'
_publ_section_title
;
 Solid-state thermo- and photochromism in
 N,N′-bis(5-X-salicylidene)diamines (X = H, Br)
;
_journal_issue                   30
_journal_name_full               'RSC Advances'
_journal_page_first              11379
_journal_paper_doi               10.1039/c2ra21631k
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.732(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3048(4)
_cell_length_b                   6.2025(3)
_cell_length_c                   35.783(2)
_cell_measurement_reflns_used    3684
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      25.3978
_cell_measurement_theta_min      2.2835
_cell_volume                     1613.15(15)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
;
_computing_molecular_graphics    PLATON
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '250 images, ΔΦ 0.75°'
_diffrn_radiation_monochromator  'Zr filter'
_diffrn_radiation_source         'RU200 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0552
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2997
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2989
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.0696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1314
_reflns_number_gt                2258
_reflns_number_total             2989
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ra21631k.txt
_cod_data_source_block           safin21
_cod_original_cell_volume        1613.17(16)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7238729
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7767(3) 0.7869(4) 0.08898(6) 0.0451(5) Uani 1 1 d .
H1 H 0.7283 0.9253 0.0897 0.054 Uiso 1 1 calc R
C2 C 0.8250(3) 0.6758(4) 0.12240(6) 0.0462(6) Uani 1 1 d .
C3 C 0.9032(4) 0.4690(4) 0.12101(7) 0.0525(6) Uani 1 1 d .
H3 H 0.9365 0.3933 0.1431 0.063 Uiso 1 1 calc R
C4 C 0.9303(4) 0.3788(4) 0.08666(7) 0.0523(6) Uani 1 1 d .
H4 H 0.9826 0.2424 0.0859 0.063 Uiso 1 1 calc R
C5 C 0.8813(4) 0.4872(4) 0.05355(7) 0.0482(6) Uani 1 1 d .
H5 H 0.9017 0.4247 0.0307 0.058 Uiso 1 1 calc R
C6 C 0.8004(3) 0.6923(4) 0.05443(6) 0.0450(6) Uani 1 1 d .
N7 N 0.7527(3) 0.8129(3) 0.02103(5) 0.0475(5) Uani 1 1 d .
C8 C 0.6865(3) 0.7162(4) -0.00920(7) 0.0477(6) Uani 1 1 d .
H8 H 0.6537 0.5718 -0.0077 0.057 Uiso 1 1 calc R
C9 C 0.6607(3) 0.8216(4) -0.04548(7) 0.0443(6) Uani 1 1 d .
C10 C 0.5872(4) 0.7076(4) -0.07747(7) 0.0507(6) Uani 1 1 d .
H10 H 0.5425 0.5688 -0.0746 0.061 Uiso 1 1 calc R
C11 C 0.5796(4) 0.7956(4) -0.11285(7) 0.0570(7) Uani 1 1 d .
H11 H 0.5300 0.7180 -0.1337 0.068 Uiso 1 1 calc R
C12 C 0.6479(4) 1.0038(4) -0.11696(7) 0.0583(7) Uani 1 1 d .
H12 H 0.6451 1.0637 -0.1408 0.070 Uiso 1 1 calc R
C13 C 0.7193(4) 1.1221(4) -0.08624(7) 0.0543(6) Uani 1 1 d .
H13 H 0.7651 1.2600 -0.0895 0.065 Uiso 1 1 calc R
C14 C 0.7228(3) 1.0350(4) -0.05039(7) 0.0463(6) Uani 1 1 d .
O15 O 0.7893(3) 1.1564(3) -0.02052(5) 0.0645(6) Uani 1 1 d .
H15 H 0.7981 1.0819 -0.0015 0.097 Uiso 1 1 calc R
N16 N 0.7962(3) 0.7863(3) 0.15659(5) 0.0500(5) Uani 1 1 d .
C17 C 0.8171(3) 0.6912(4) 0.18846(7) 0.0480(6) Uani 1 1 d .
H17 H 0.8543 0.5478 0.1894 0.058 Uiso 1 1 calc R
C18 C 0.7850(3) 0.7992(4) 0.22315(6) 0.0442(6) Uani 1 1 d .
C19 C 0.8152(4) 0.6897(4) 0.25738(7) 0.0545(7) Uani 1 1 d .
H19 H 0.8611 0.5498 0.2576 0.065 Uiso 1 1 calc R
C20 C 0.7785(4) 0.7841(5) 0.29085(7) 0.0633(8) Uani 1 1 d .
H20 H 0.8007 0.7094 0.3134 0.076 Uiso 1 1 calc R
C21 C 0.7077(4) 0.9927(5) 0.29028(8) 0.0650(8) Uani 1 1 d .
H21 H 0.6803 1.0564 0.3126 0.078 Uiso 1 1 calc R
C22 C 0.6777(4) 1.1063(4) 0.25704(7) 0.0560(7) Uani 1 1 d .
H22 H 0.6308 1.2457 0.2571 0.067 Uiso 1 1 calc R
C23 C 0.7172(4) 1.0131(4) 0.22347(7) 0.0477(6) Uani 1 1 d .
O24 O 0.6904(3) 1.1309(3) 0.19144(5) 0.0652(6) Uani 1 1 d .
H24 H 0.7169 1.0580 0.1736 0.098 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.6(2)
C6 C1 H1 119.7
C2 C1 H1 119.7
C1 C2 C3 119.3(2)
C1 C2 N16 116.7(2)
C3 C2 N16 124.0(2)
C4 C3 C2 119.6(2)
C4 C3 H3 120.2
C2 C3 H3 120.2
C5 C4 C3 121.3(2)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 119.8(2)
C4 C5 H5 120.1
C6 C5 H5 120.1
C1 C6 C5 119.4(2)
C1 C6 N7 118.8(2)
C5 C6 N7 121.7(2)
C8 N7 C6 120.0(2)
N7 C8 C9 123.1(2)
N7 C8 H8 118.4
C9 C8 H8 118.4
C10 C9 C14 118.1(2)
C10 C9 C8 120.5(2)
C14 C9 C8 121.2(2)
C11 C10 C9 121.8(2)
C11 C10 H10 119.1
C9 C10 H10 119.1
C10 C11 C12 118.8(2)
C10 C11 H11 120.6
C12 C11 H11 120.6
C13 C12 C11 121.2(2)
C13 C12 H12 119.4
C11 C12 H12 119.4
C12 C13 C14 119.9(2)
C12 C13 H13 120.0
C14 C13 H13 120.0
O15 C14 C13 118.9(2)
O15 C14 C9 121.0(2)
C13 C14 C9 120.1(2)
C14 O15 H15 109.5
C17 N16 C2 121.64(19)
N16 C17 C18 122.3(2)
N16 C17 H17 118.8
C18 C17 H17 118.8
C19 C18 C23 118.2(2)
C19 C18 C17 120.0(2)
C23 C18 C17 121.7(2)
C20 C19 C18 121.7(2)
C20 C19 H19 119.2
C18 C19 H19 119.2
C19 C20 C21 119.0(2)
C19 C20 H20 120.5
C21 C20 H20 120.5
C22 C21 C20 120.9(3)
C22 C21 H21 119.6
C20 C21 H21 119.6
C21 C22 C23 120.2(3)
C21 C22 H22 119.9
C23 C22 H22 119.9
O24 C23 C22 118.7(2)
O24 C23 C18 121.3(2)
C22 C23 C18 120.0(2)
C23 O24 H24 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.395(3)
C1 C2 1.395(3)
C1 H1 0.9300
C2 C3 1.407(3)
C2 N16 1.436(3)
C3 C4 1.383(3)
C3 H3 0.9300
C4 C5 1.378(3)
C4 H4 0.9300
C5 C6 1.404(3)
C5 H5 0.9300
C6 N7 1.423(3)
N7 C8 1.288(3)
C8 C9 1.449(3)
C8 H8 0.9300
C9 C10 1.406(3)
C9 C14 1.416(3)
C10 C11 1.375(3)
C10 H10 0.9300
C11 C12 1.397(4)
C11 H11 0.9300
C12 C13 1.380(4)
C12 H12 0.9300
C13 C14 1.390(3)
C13 H13 0.9300
C14 O15 1.357(3)
O15 H15 0.8200
N16 C17 1.280(3)
C17 C18 1.450(3)
C17 H17 0.9300
C18 C19 1.399(3)
C18 C23 1.416(3)
C19 C20 1.383(3)
C19 H19 0.9300
C20 C21 1.393(4)
C20 H20 0.9300
C21 C22 1.381(4)
C21 H21 0.9300
C22 C23 1.389(3)
C22 H22 0.9300
C23 O24 1.357(3)
O24 H24 0.8200
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
C6 C1 C2 C3 1.8(4)
C6 C1 C2 N16 179.8(2)
C1 C2 C3 C4 -0.2(4)
N16 C2 C3 C4 -178.1(2)
C2 C3 C4 C5 -0.3(4)
C3 C4 C5 C6 -0.7(4)
C2 C1 C6 C5 -2.8(4)
C2 C1 C6 N7 -178.8(2)
C4 C5 C6 C1 2.3(4)
C4 C5 C6 N7 178.1(2)
C1 C6 N7 C8 -146.1(2)
C5 C6 N7 C8 38.0(4)
C6 N7 C8 C9 -170.4(2)
N7 C8 C9 C10 -179.8(2)
N7 C8 C9 C14 5.7(4)
C14 C9 C10 C11 1.9(4)
C8 C9 C10 C11 -172.8(2)
C9 C10 C11 C12 0.3(4)
C10 C11 C12 C13 -1.0(4)
C11 C12 C13 C14 -0.5(4)
C12 C13 C14 O15 -178.3(2)
C12 C13 C14 C9 2.8(4)
C10 C9 C14 O15 177.7(2)
C8 C9 C14 O15 -7.6(3)
C10 C9 C14 C13 -3.5(3)
C8 C9 C14 C13 171.2(2)
C1 C2 N16 C17 172.4(2)
C3 C2 N16 C17 -9.7(4)
C2 N16 C17 C18 -178.7(2)
N16 C17 C18 C19 -178.1(2)
N16 C17 C18 C23 4.1(4)
C23 C18 C19 C20 0.8(4)
C17 C18 C19 C20 -177.1(2)
C18 C19 C20 C21 0.7(4)
C19 C20 C21 C22 -1.3(4)
C20 C21 C22 C23 0.3(4)
C21 C22 C23 O24 -178.4(3)
C21 C22 C23 C18 1.3(4)
C19 C18 C23 O24 177.9(3)
C17 C18 C23 O24 -4.3(4)
C19 C18 C23 C22 -1.8(4)
C17 C18 C23 C22 176.1(2)
