#------------------------------------------------------------------------------
#$Date: 2019-09-06 09:52:50 +0200 (vie 06 de sep de 2019) $
#$Revision: 218045 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/36/7233694.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_7233694
loop_
_publ_author_name
'Pengchong Xue'
'Boqi Yao'
'Jiabao Sun'
'Qiuxia Xu'
'Peng Chen'
'Zhenqi Zhang'
'Ran Lu'
_publ_section_title
;
 Phenothiazine-based benzoxazole derivates exhibiting mechanochromic
 luminescence: the effect of a bromine atom
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              3942
_journal_page_last               3950
_journal_paper_doi               10.1039/C4TC00061G
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C23 H16 Br N2 O S'
_chemical_formula_weight         448.35
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                93.04(3)
_cell_angle_beta                 91.76(3)
_cell_angle_gamma                99.00(3)
_cell_formula_units_Z            2
_cell_length_a                   4.1159(8)
_cell_length_b                   11.407(2)
_cell_length_c                   20.162(4)
_cell_measurement_reflns_used    7949
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      57.28
_cell_measurement_theta_min      6.08
_cell_volume                     932.9(3)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku Corporation, 1998)'
_computing_data_reduction
'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8887
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.04
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.332
_exptl_absorpt_correction_T_max  0.792
_exptl_absorpt_correction_T_min  0.763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            yellow-green
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             454
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.835
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4103
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0627P)²+1.8885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1368
_refine_ls_wR_factor_ref         0.1606
_reflns_number_gt                3185
_reflns_number_total             4103
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            J-Mater-Chem-C-2014-2-3942-2.cif
_cod_data_source_block           d
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7233694
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.24000(12) 0.86891(4) 0.09043(2) 0.02889(18) Uani 1 1 d . . .
S1 S 0.0101(3) 0.88267(10) -0.18018(6) 0.0255(3) Uani 1 1 d . . .
N2 N -0.3436(9) 0.6264(3) -0.17519(18) 0.0214(8) Uani 1 1 d . . .
O1 O 0.6608(9) 0.8298(3) -0.52125(16) 0.0268(7) Uani 1 1 d . . .
C23 C -0.1231(11) 0.6791(4) 0.0061(2) 0.0248(10) Uani 1 1 d . . .
H23A H -0.1597 0.6394 0.0449 0.030 Uiso 1 1 calc R . .
C11 C 0.1595(11) 0.7908(4) -0.3001(2) 0.0223(9) Uani 1 1 d . . .
H11A H 0.2920 0.8642 -0.3027 0.027 Uiso 1 1 calc R . .
C22 C 0.0599(11) 0.7930(4) 0.0086(2) 0.0237(9) Uani 1 1 d . . .
C10 C 0.1302(11) 0.7091(4) -0.3548(2) 0.0223(9) Uani 1 1 d . . .
C19 C -0.2055(10) 0.6817(4) -0.1138(2) 0.0188(8) Uani 1 1 d . . .
C20 C -0.0229(11) 0.7977(4) -0.1097(2) 0.0212(9) Uani 1 1 d . . .
C12 C -0.0025(11) 0.7660(4) -0.2421(2) 0.0211(9) Uani 1 1 d . . .
N1 N 0.6195(10) 0.6465(3) -0.57329(19) 0.0256(8) Uani 1 1 d . . .
C15 C -0.0752(12) 0.5988(4) -0.3496(2) 0.0250(10) Uani 1 1 d . . .
H15A H -0.1045 0.5435 -0.3857 0.030 Uiso 1 1 calc R . .
C24 C -0.2502(11) 0.6252(4) -0.0542(2) 0.0231(9) Uani 1 1 d . . .
H24A H -0.3694 0.5488 -0.0552 0.028 Uiso 1 1 calc R . .
C5 C 0.7922(11) 0.7295(4) -0.6122(2) 0.0232(9) Uani 1 1 d . . .
C17 C -0.5830(11) 0.5191(4) -0.1741(2) 0.0235(9) Uani 1 1 d . . .
H17A H -0.8080 0.5212 -0.1768 0.028 Uiso 1 1 calc R . .
C9 C 0.3102(11) 0.7397(4) -0.4143(2) 0.0252(10) Uani 1 1 d . . .
H9A H 0.4002 0.8194 -0.4165 0.030 Uiso 1 1 calc R . .
C21 C 0.1136(11) 0.8513(4) -0.0497(2) 0.0216(9) Uani 1 1 d . . .
H21A H 0.2411 0.9263 -0.0485 0.026 Uiso 1 1 calc R . .
C14 C -0.2328(11) 0.5721(4) -0.2916(2) 0.0233(9) Uani 1 1 d . . .
H14A H -0.3678 0.4991 -0.2892 0.028 Uiso 1 1 calc R . .
C18 C -0.4484(12) 0.4013(4) -0.1683(2) 0.0247(10) Uani 1 1 d . . .
H18A H -0.6287 0.3368 -0.1682 0.037 Uiso 1 1 calc R . .
H18B H -0.3179 0.4047 -0.1278 0.037 Uiso 1 1 calc R . .
H18C H -0.3146 0.3891 -0.2055 0.037 Uiso 1 1 calc R . .
C6 C 0.9284(12) 0.7161(4) -0.6742(2) 0.0286(10) Uani 1 1 d . . .
H6A H 0.9155 0.6420 -0.6966 0.034 Uiso 1 1 calc R . .
C13 C -0.1921(11) 0.6547(4) -0.2352(2) 0.0208(9) Uani 1 1 d . . .
C8 C 0.3614(12) 0.6686(4) -0.4655(2) 0.0249(10) Uani 1 1 d . . .
H8A H 0.2737 0.5884 -0.4651 0.030 Uiso 1 1 calc R . .
C4 C 0.8231(12) 0.8428(4) -0.5797(2) 0.0258(10) Uani 1 1 d . . .
C7 C 0.5456(12) 0.7087(4) -0.5216(2) 0.0237(9) Uani 1 1 d . . .
C3 C 0.9761(13) 0.9457(4) -0.6051(3) 0.0327(11) Uani 1 1 d . . .
H3A H 0.9906 1.0194 -0.5822 0.039 Uiso 1 1 calc R . .
C2 C 1.1072(13) 0.9325(4) -0.6668(3) 0.0312(11) Uani 1 1 d . . .
H2A H 1.2124 0.9993 -0.6865 0.037 Uiso 1 1 calc R . .
C1 C 1.0848(12) 0.8195(5) -0.7009(2) 0.0316(11) Uani 1 1 d . . .
H1A H 1.1771 0.8140 -0.7422 0.038 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'
Br Br -0.2901 2.4595 '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
C20 S1 C12 98.9(2) . .
C13 N2 C19 120.4(4) . .
C13 N2 C17 118.8(4) . .
C19 N2 C17 118.6(4) . .
C4 O1 C7 104.0(3) . .
C24 C23 C22 120.0(4) . .
C12 C11 C10 122.0(4) . .
C21 C22 C23 119.5(4) . .
C21 C22 Br1 119.5(3) . .
C23 C22 Br1 121.0(3) . .
C11 C10 C15 117.7(4) . .
C11 C10 C9 119.5(4) . .
C15 C10 C9 122.7(4) . .
C24 C19 C20 116.7(4) . .
C24 C19 N2 121.6(4) . .
C20 C19 N2 121.7(4) . .
C21 C20 C19 121.5(4) . .
C21 C20 S1 118.0(3) . .
C19 C20 S1 120.3(3) . .
C11 C12 C13 120.6(4) . .
C11 C12 S1 118.0(3) . .
C13 C12 S1 121.2(3) . .
C7 N1 C5 104.4(4) . .
C14 C15 C10 120.8(4) . .
C23 C24 C19 122.2(4) . .
N1 C5 C6 130.8(4) . .
N1 C5 C4 109.5(4) . .
C6 C5 C4 119.7(4) . .
N2 C17 C18 117.0(4) . .
C8 C9 C10 128.2(5) . .
C22 C21 C20 120.1(4) . .
C15 C14 C13 121.0(4) . .
C1 C6 C5 116.6(4) . .
C12 C13 N2 121.1(4) . .
C12 C13 C14 117.6(4) . .
N2 C13 C14 121.3(4) . .
C9 C8 C7 123.4(4) . .
C3 C4 O1 128.2(4) . .
C3 C4 C5 124.7(4) . .
O1 C4 C5 107.1(4) . .
N1 C7 O1 115.0(4) . .
N1 C7 C8 128.5(4) . .
O1 C7 C8 116.4(4) . .
C4 C3 C2 115.6(5) . .
C3 C2 C1 121.5(4) . .
C6 C1 C2 122.0(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C22 1.896(5) .
S1 C20 1.758(4) .
S1 C12 1.769(5) .
N2 C13 1.408(5) .
N2 C19 1.420(6) .
N2 C17 1.448(6) .
O1 C4 1.377(5) .
O1 C7 1.388(5) .
C23 C24 1.382(7) .
C23 C22 1.394(7) .
C11 C12 1.384(6) .
C11 C10 1.395(6) .
C22 C21 1.386(6) .
C10 C15 1.412(7) .
C10 C9 1.459(6) .
C19 C24 1.396(6) .
C19 C20 1.413(6) .
C20 C21 1.389(6) .
C12 C13 1.399(6) .
N1 C7 1.301(6) .
N1 C5 1.386(6) .
C15 C14 1.380(6) .
C5 C6 1.397(6) .
C5 C4 1.403(6) .
C17 C18 1.539(6) .
C9 C8 1.321(7) .
C14 C13 1.426(6) .
C6 C1 1.394(7) .
C8 C7 1.436(6) .
C4 C3 1.374(7) .
C3 C2 1.383(7) .
C2 C1 1.417(7) .
