#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/50/7235044.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_7235044
loop_
_publ_author_name
'Xiao-Lin Lu'
'Min Xia'
_publ_section_title
;
 Multi-stimuli response of a novel half-cut cruciform and its application
 as a security ink
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              9350
_journal_page_last               9358
_journal_paper_doi               10.1039/C6TC02618D
_journal_volume                  4
_journal_year                    2016
_chemical_formula_moiety         'C23 H20 N2 S'
_chemical_formula_sum            'C23 H20 N2 S'
_chemical_formula_weight         356.47
_chemical_melting_point          388.8(7)
_chemical_name_systematic
'(E)-2'-[2-(benzo[d]thiazol-2-yl)vinyl]-N, N-dimethyl-(1,1'-biphenyl)-4-amine'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 99.738(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5537(8)
_cell_length_b                   6.3103(4)
_cell_length_c                   23.6534(17)
_cell_measurement_reflns_used    1938
_cell_measurement_temperature    170.
_cell_measurement_theta_max      29.6016
_cell_measurement_theta_min      3.2218
_cell_volume                     1846.8(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424385000
_diffrn_orient_matrix_UB_12      -0.0142350000
_diffrn_orient_matrix_UB_13      0.0159793000
_diffrn_orient_matrix_UB_21      -0.0371176000
_diffrn_orient_matrix_UB_22      -0.0145711000
_diffrn_orient_matrix_UB_23      -0.0258398000
_diffrn_orient_matrix_UB_31      0.0103876000
_diffrn_orient_matrix_UB_32      -0.1105918000
_diffrn_orient_matrix_UB_33      0.0013639000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            7064
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.34
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0437
_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)+(0.0432P)²+0.6367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1125
_reflns_number_gt                2598
_reflns_number_total             3377
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2016-4-9350.cif
_cod_data_source_block           150702_xiamin_0630
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '388.05-389.45' was changed
to '388.8(7)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               7235044
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.14051(4) 0.19230(9) 0.07992(2) 0.03735(18) Uani 1 d . . .
N1 N 0.12174(13) 0.1842(3) 0.18831(7) 0.0307(4) Uani 1 d . . .
N2 N 0.27346(13) 0.5828(3) -0.14839(7) 0.0332(4) Uani 1 d . . .
C1 C 0.06474(16) -0.0079(3) 0.10266(10) 0.0353(5) Uani 1 d . . .
C2 C 0.01166(19) -0.1753(4) 0.07123(12) 0.0519(7) Uani 1 d . . .
H2 H 0.0136 -0.1919 0.0315 0.062 Uiso 1 calc . . R
C3 C -0.04454(19) -0.3178(4) 0.10061(15) 0.0616(9) Uani 1 d . . .
H3 H -0.0820 -0.4335 0.0806 0.074 Uiso 1 calc . . R
C4 C -0.04600(19) -0.2920(4) 0.15814(15) 0.0615(8) Uani 1 d . . .
H4 H -0.0848 -0.3913 0.1770 0.074 Uiso 1 calc . . R
C5 C 0.00593(17) -0.1298(4) 0.18915(12) 0.0496(7) Uani 1 d . . .
H5 H 0.0030 -0.1151 0.2288 0.060 Uiso 1 calc . . R
C6 C 0.06361(16) 0.0146(4) 0.16128(10) 0.0366(5) Uani 1 d . . .
C7 C 0.16694(15) 0.2905(3) 0.14969(9) 0.0293(5) Uani 1 d . . .
C8 C 0.23670(16) 0.4726(3) 0.16261(9) 0.0324(5) Uani 1 d . . .
H8 H 0.2584 0.5107 0.2017 0.039 Uiso 1 calc . . R
C9 C 0.27214(15) 0.5893(3) 0.12313(9) 0.0291(5) Uani 1 d . . .
H9 H 0.2466 0.5491 0.0845 0.035 Uiso 1 calc . . R
C10 C 0.34535(15) 0.7719(3) 0.13074(9) 0.0285(5) Uani 1 d . . .
C11 C 0.38028(16) 0.8578(3) 0.18552(9) 0.0353(5) Uani 1 d . . .
H11 H 0.3583 0.7933 0.2180 0.042 Uiso 1 calc . . R
C12 C 0.44587(17) 1.0340(4) 0.19302(10) 0.0412(6) Uani 1 d . . .
H12 H 0.4684 1.0907 0.2303 0.049 Uiso 1 calc . . R
C13 C 0.47890(17) 1.1280(4) 0.14618(11) 0.0414(6) Uani 1 d . . .
H13 H 0.5239 1.2500 0.1512 0.050 Uiso 1 calc . . R
C14 C 0.44662(16) 1.0451(3) 0.09215(10) 0.0354(5) Uani 1 d . . .
H14 H 0.4703 1.1103 0.0602 0.043 Uiso 1 calc . . R
C15 C 0.37972(15) 0.8669(3) 0.08336(9) 0.0290(5) Uani 1 d . . .
C16 C 0.34715(15) 0.7874(3) 0.02353(9) 0.0284(5) Uani 1 d . . .
C17 C 0.37296(15) 0.5838(3) 0.00728(9) 0.0315(5) Uani 1 d . . .
H17 H 0.4080 0.4893 0.0357 0.038 Uiso 1 calc . . R
C18 C 0.34912(15) 0.5157(3) -0.04876(9) 0.0318(5) Uani 1 d . . .
H18 H 0.3695 0.3769 -0.0582 0.038 Uiso 1 calc . . R
C19 C 0.29534(14) 0.6474(3) -0.09198(9) 0.0282(5) Uani 1 d . . .
C20 C 0.26595(16) 0.8501(3) -0.07528(9) 0.0325(5) Uani 1 d . . .
H20 H 0.2271 0.9427 -0.1031 0.039 Uiso 1 calc . . R
C21 C 0.29258(16) 0.9160(3) -0.01942(9) 0.0319(5) Uani 1 d . . .
H21 H 0.2729 1.0551 -0.0098 0.038 Uiso 1 calc . . R
C22 C 0.22346(18) 0.7282(4) -0.19197(9) 0.0405(5) Uani 1 d . . .
H22A H 0.1546 0.7776 -0.1825 0.061 Uiso 1 calc . . GR
H22B H 0.2104 0.6562 -0.2292 0.061 Uiso 1 calc . . GR
H22C H 0.2714 0.8497 -0.1938 0.061 Uiso 1 calc . . GR
C23 C 0.31755(18) 0.3857(4) -0.16612(10) 0.0415(6) Uani 1 d . . .
H23A H 0.3967 0.3924 -0.1584 0.062 Uiso 1 calc . . GR
H23B H 0.2927 0.3640 -0.2073 0.062 Uiso 1 calc . . GR
H23C H 0.2931 0.2676 -0.1447 0.062 Uiso 1 calc . . GR
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'
S S 0.1246 0.1234 '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
C1 S1 C7 89.53(10) . .
C7 N1 C6 108.86(18) . .
C19 N2 C22 119.66(17) . .
C19 N2 C23 120.68(17) . .
C22 N2 C23 118.68(18) . .
C2 C1 S1 129.0(2) . .
C2 C1 C6 121.5(2) . .
C6 C1 S1 109.55(16) . .
C1 C2 H2 121.4 . .
C1 C2 C3 117.3(3) . .
C3 C2 H2 121.4 . .
C2 C3 H3 119.7 . .
C4 C3 C2 120.6(2) . .
C4 C3 H3 119.7 . .
C3 C4 H4 118.7 . .
C5 C4 C3 122.6(3) . .
C5 C4 H4 118.7 . .
C4 C5 H5 120.8 . .
C4 C5 C6 118.4(3) . .
C6 C5 H5 120.8 . .
N1 C6 C1 116.27(19) . .
N1 C6 C5 124.0(2) . .
C1 C6 C5 119.7(2) . .
N1 C7 S1 115.77(15) . .
N1 C7 C8 124.55(19) . .
C8 C7 S1 119.65(15) . .
C7 C8 H8 118.1 . .
C9 C8 C7 123.8(2) . .
C9 C8 H8 118.1 . .
C8 C9 H9 115.5 . .
C8 C9 C10 129.0(2) . .
C10 C9 H9 115.5 . .
C11 C10 C9 120.53(19) . .
C15 C10 C9 120.62(18) . .
C15 C10 C11 118.84(18) . .
C10 C11 H11 119.4 . .
C12 C11 C10 121.1(2) . .
C12 C11 H11 119.4 . .
C11 C12 H12 120.1 . .
C11 C12 C13 119.9(2) . .
C13 C12 H12 120.1 . .
C12 C13 H13 120.0 . .
C14 C13 C12 120.0(2) . .
C14 C13 H13 120.0 . .
C13 C14 H14 119.4 . .
C13 C14 C15 121.2(2) . .
C15 C14 H14 119.4 . .
C10 C15 C16 122.87(18) . .
C14 C15 C10 118.91(19) . .
C14 C15 C16 118.22(19) . .
C17 C16 C15 122.12(18) . .
C21 C16 C15 121.35(18) . .
C21 C16 C17 116.49(19) . .
C16 C17 H17 119.0 . .
C18 C17 C16 122.00(19) . .
C18 C17 H17 119.0 . .
C17 C18 H18 119.4 . .
C17 C18 C19 121.12(19) . .
C19 C18 H18 119.4 . .
N2 C19 C18 121.59(18) . .
N2 C19 C20 121.50(18) . .
C18 C19 C20 116.90(19) . .
C19 C20 H20 119.6 . .
C21 C20 C19 120.90(19) . .
C21 C20 H20 119.6 . .
C16 C21 H21 118.7 . .
C20 C21 C16 122.54(19) . .
C20 C21 H21 118.7 . .
N2 C22 H22A 109.5 . .
N2 C22 H22B 109.5 . .
N2 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
N2 C23 H23A 109.5 . .
N2 C23 H23B 109.5 . .
N2 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.721(2) .
S1 C7 1.741(2) .
N1 C6 1.389(3) .
N1 C7 1.335(3) .
N2 C19 1.378(3) .
N2 C22 1.442(3) .
N2 C23 1.452(3) .
C1 C2 1.395(3) .
C1 C6 1.396(3) .
C2 H2 0.9500 .
C2 C3 1.398(4) .
C3 H3 0.9500 .
C3 C4 1.374(4) .
C4 H4 0.9500 .
C4 C5 1.360(4) .
C5 H5 0.9500 .
C5 C6 1.397(3) .
C7 C8 1.446(3) .
C8 H8 0.9500 .
C8 C9 1.324(3) .
C9 H9 0.9500 .
C9 C10 1.466(3) .
C10 C11 1.405(3) .
C10 C15 1.402(3) .
C11 H11 0.9500 .
C11 C12 1.377(3) .
C12 H12 0.9500 .
C12 C13 1.381(3) .
C13 H13 0.9500 .
C13 C14 1.377(3) .
C14 H14 0.9500 .
C14 C15 1.398(3) .
C15 C16 1.492(3) .
C16 C17 1.395(3) .
C16 C21 1.387(3) .
C17 H17 0.9500 .
C17 C18 1.378(3) .
C18 H18 0.9500 .
C18 C19 1.400(3) .
C19 C20 1.406(3) .
C20 H20 0.9500 .
C20 C21 1.372(3) .
C21 H21 0.9500 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
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
S1 C1 C2 C3 179.80(17) . . . .
S1 C1 C6 N1 -0.6(2) . . . .
S1 C1 C6 C5 179.43(16) . . . .
S1 C7 C8 C9 9.0(3) . . . .
N1 C7 C8 C9 -172.9(2) . . . .
N2 C19 C20 C21 -177.00(18) . . . .
C1 S1 C7 N1 -0.68(16) . . . .
C1 S1 C7 C8 177.58(17) . . . .
C1 C2 C3 C4 -0.3(3) . . . .
C2 C1 C6 N1 178.30(18) . . . .
C2 C1 C6 C5 -1.7(3) . . . .
C2 C3 C4 C5 0.0(4) . . . .
C3 C4 C5 C6 -0.6(4) . . . .
C4 C5 C6 N1 -178.7(2) . . . .
C4 C5 C6 C1 1.4(3) . . . .
C6 N1 C7 S1 0.5(2) . . . .
C6 N1 C7 C8 -177.69(18) . . . .
C6 C1 C2 C3 1.2(3) . . . .
C7 S1 C1 C2 -178.1(2) . . . .
C7 S1 C1 C6 0.65(16) . . . .
C7 N1 C6 C1 0.1(2) . . . .
C7 N1 C6 C5 -179.9(2) . . . .
C7 C8 C9 C10 -177.84(19) . . . .
C8 C9 C10 C11 -5.9(3) . . . .
C8 C9 C10 C15 175.6(2) . . . .
C9 C10 C11 C12 -177.63(19) . . . .
C9 C10 C15 C14 177.88(17) . . . .
C9 C10 C15 C16 -1.5(3) . . . .
C10 C11 C12 C13 -0.4(3) . . . .
C10 C15 C16 C17 -61.0(3) . . . .
C10 C15 C16 C21 121.3(2) . . . .
C11 C10 C15 C14 -0.7(3) . . . .
C11 C10 C15 C16 179.95(17) . . . .
C11 C12 C13 C14 -0.3(3) . . . .
C12 C13 C14 C15 0.5(3) . . . .
C13 C14 C15 C10 0.0(3) . . . .
C13 C14 C15 C16 179.37(18) . . . .
C14 C15 C16 C17 119.6(2) . . . .
C14 C15 C16 C21 -58.1(2) . . . .
C15 C10 C11 C12 0.9(3) . . . .
C15 C16 C17 C18 -175.59(18) . . . .
C15 C16 C21 C20 177.02(18) . . . .
C16 C17 C18 C19 -1.5(3) . . . .
C17 C16 C21 C20 -0.8(3) . . . .
C17 C18 C19 N2 178.38(18) . . . .
C17 C18 C19 C20 -0.8(3) . . . .
C18 C19 C20 C21 2.2(3) . . . .
C19 C20 C21 C16 -1.4(3) . . . .
C21 C16 C17 C18 2.2(3) . . . .
C22 N2 C19 C18 -176.42(18) . . . .
C22 N2 C19 C20 2.7(3) . . . .
C23 N2 C19 C18 -7.9(3) . . . .
C23 N2 C19 C20 171.24(18) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132496617
