#------------------------------------------------------------------------------
#$Date: 2019-09-25 11:01:39 +0300 (Wed, 25 Sep 2019) $
#$Revision: 218813 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/41/7234129.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_7234129
loop_
_publ_author_name
'Qingsong Liu'
'Xiaoqing Wang'
'Hui Yan'
'Yanping Wu'
'Zhenyu Li'
'Shuwen Gong'
'Peng Liu'
'Zhipeng Liu'
_publ_section_title
;
 Benzothiazole-enamide-based BF2 complexes: luminophores exhibiting
 aggregation-induced emission, tunable emission and highly efficient
 solid-state emission
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              2953
_journal_page_last               2959
_journal_paper_doi               10.1039/C4TC02876G
_journal_volume                  3
_journal_year                    2015
_chemical_formula_sum            'C23 H19 B F2 N2 S'
_chemical_formula_weight         404.27
_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_H-M   '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                 117.220(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.3993(10)
_cell_length_b                   12.7664(9)
_cell_length_c                   15.0074(17)
_cell_measurement_reflns_used    1629
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.4810
_cell_measurement_theta_min      3.2010
_cell_volume                     1942.1(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12800
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3424
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1042
_refine_ls_R_factor_gt           0.0520
_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)+(0.0407P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2009
_reflns_number_total             3424
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000002.cif
_cod_data_source_block           PCOD1000002
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7234129
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.82592(9) 0.60961(7) 0.10596(6) 0.0528(3) Uani 1 1 d . . .
F1 F 0.75496(19) 0.72248(14) 0.39387(13) 0.0638(6) Uani 1 1 d . . .
F2 F 0.94283(17) 0.78864(14) 0.40286(12) 0.0627(6) Uani 1 1 d . . .
N1 N 0.8134(2) 0.67947(18) 0.26253(17) 0.0396(6) Uani 1 1 d . . .
N2 N 0.7363(2) 0.85895(18) 0.27650(17) 0.0375(6) Uani 1 1 d . . .
C1 C 0.8521(3) 0.5220(2) 0.2017(2) 0.0455(8) Uani 1 1 d . . .
C2 C 0.8802(3) 0.4161(3) 0.2064(3) 0.0553(9) Uani 1 1 d . . .
H2 H 0.8874 0.3830 0.1539 0.066 Uiso 1 1 calc R . .
C3 C 0.8971(3) 0.3607(3) 0.2899(3) 0.0639(10) Uani 1 1 d . . .
H3 H 0.9154 0.2894 0.2937 0.077 Uiso 1 1 calc R . .
C4 C 0.8874(3) 0.4098(3) 0.3688(3) 0.0643(10) Uani 1 1 d . . .
H4 H 0.8998 0.3710 0.4248 0.077 Uiso 1 1 calc R . .
C5 C 0.8594(3) 0.5157(3) 0.3654(2) 0.0532(9) Uani 1 1 d . . .
H5 H 0.8527 0.5483 0.4183 0.064 Uiso 1 1 calc R . .
C6 C 0.8417(3) 0.5718(2) 0.2811(2) 0.0416(8) Uani 1 1 d . . .
C7 C 0.8034(3) 0.7103(2) 0.1739(2) 0.0392(7) Uani 1 1 d . . .
C8 C 0.7736(3) 0.8123(2) 0.1387(2) 0.0430(8) Uani 1 1 d . . .
H8 H 0.7799 0.8323 0.0815 0.052 Uiso 1 1 calc R . .
C9 C 0.7346(3) 0.8846(2) 0.1890(2) 0.0373(7) Uani 1 1 d . . .
C10 C 0.6924(3) 0.9904(2) 0.1428(2) 0.0399(7) Uani 1 1 d . . .
C11 C 0.7783(3) 1.0445(3) 0.1176(2) 0.0533(9) Uani 1 1 d . . .
H11 H 0.8570 1.0133 0.1276 0.064 Uiso 1 1 calc R . .
C12 C 0.7484(4) 1.1447(3) 0.0778(3) 0.0704(11) Uani 1 1 d . . .
H12 H 0.8075 1.1810 0.0624 0.084 Uiso 1 1 calc R . .
C13 C 0.6303(4) 1.1900(3) 0.0612(3) 0.0712(11) Uani 1 1 d . . .
H13 H 0.6100 1.2574 0.0349 0.085 Uiso 1 1 calc R . .
C14 C 0.5435(4) 1.1365(3) 0.0832(2) 0.0579(10) Uani 1 1 d . . .
H14 H 0.4634 1.1673 0.0705 0.069 Uiso 1 1 calc R . .
C15 C 0.5729(3) 1.0369(3) 0.1243(2) 0.0483(8) Uani 1 1 d . . .
H15 H 0.5131 1.0012 0.1395 0.058 Uiso 1 1 calc R . .
C16 C 0.6712(3) 0.9251(2) 0.3195(2) 0.0376(7) Uani 1 1 d . . .
C17 C 0.5461(3) 0.8948(2) 0.3047(2) 0.0444(8) Uani 1 1 d . . .
C18 C 0.4849(3) 0.9552(3) 0.3475(2) 0.0569(9) Uani 1 1 d . . .
H18 H 0.4026 0.9353 0.3404 0.068 Uiso 1 1 calc R . .
C19 C 0.5436(4) 1.0440(3) 0.4004(3) 0.0610(10) Uani 1 1 d . . .
H19 H 0.5006 1.0842 0.4282 0.073 Uiso 1 1 calc R . .
C20 C 0.6656(4) 1.0739(3) 0.4126(2) 0.0531(9) Uani 1 1 d . . .
H20 H 0.7039 1.1347 0.4483 0.064 Uiso 1 1 calc R . .
C21 C 0.7333(3) 1.0154(2) 0.3728(2) 0.0420(8) Uani 1 1 d . . .
C22 C 0.8635(3) 1.0512(3) 0.3841(2) 0.0616(10) Uani 1 1 d . . .
H22A H 0.8518 1.0858 0.3238 0.092 Uiso 1 1 calc R . .
H22B H 0.9206 0.9919 0.3964 0.092 Uiso 1 1 calc R . .
H22C H 0.9021 1.0991 0.4394 0.092 Uiso 1 1 calc R . .
C23 C 0.4746(3) 0.8033(3) 0.2368(3) 0.0662(10) Uani 1 1 d . . .
H23A H 0.5313 0.7431 0.2561 0.099 Uiso 1 1 calc R . .
H23B H 0.4511 0.8213 0.1686 0.099 Uiso 1 1 calc R . .
H23C H 0.3962 0.7877 0.2429 0.099 Uiso 1 1 calc R . .
B1 B 0.8124(4) 0.7632(3) 0.3382(3) 0.0440(9) Uani 1 1 d . . .
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
B B 0.0013 0.0007 '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
C7 S1 C1 90.39(15) . .
C7 N1 C6 113.0(2) . .
C7 N1 B1 119.6(3) . .
C6 N1 B1 126.9(3) . .
C9 N2 C16 120.6(2) . .
C9 N2 B1 122.2(2) . .
C16 N2 B1 117.1(2) . .
C2 C1 C6 120.5(3) . .
C2 C1 S1 128.3(3) . .
C6 C1 S1 111.2(2) . .
C3 C2 C1 118.8(3) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 120.8(3) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C5 C4 C3 121.2(4) . .
C5 C4 H4 119.4 . .
C3 C4 H4 119.4 . .
C4 C5 C6 118.2(3) . .
C4 C5 H5 120.9 . .
C6 C5 H5 120.9 . .
C5 C6 C1 120.5(3) . .
C5 C6 N1 127.5(3) . .
C1 C6 N1 112.0(3) . .
N1 C7 C8 123.2(3) . .
N1 C7 S1 113.4(2) . .
C8 C7 S1 123.4(2) . .
C9 C8 C7 120.1(3) . .
C9 C8 H8 120.0 . .
C7 C8 H8 120.0 . .
N2 C9 C8 120.3(3) . .
N2 C9 C10 122.1(3) . .
C8 C9 C10 117.7(3) . .
C11 C10 C15 118.9(3) . .
C11 C10 C9 117.4(3) . .
C15 C10 C9 123.7(3) . .
C10 C11 C12 120.9(3) . .
C10 C11 H11 119.6 . .
C12 C11 H11 119.6 . .
C13 C12 C11 119.5(4) . .
C13 C12 H12 120.3 . .
C11 C12 H12 120.3 . .
C14 C13 C12 120.2(3) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C14 C15 120.9(3) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C14 C15 C10 119.6(3) . .
C14 C15 H15 120.2 . .
C10 C15 H15 120.2 . .
C17 C16 C21 122.3(3) . .
C17 C16 N2 117.4(3) . .
C21 C16 N2 120.3(3) . .
C18 C17 C16 118.0(3) . .
C18 C17 C23 120.7(3) . .
C16 C17 C23 121.1(3) . .
C19 C18 C17 121.0(3) . .
C19 C18 H18 119.5 . .
C17 C18 H18 119.5 . .
C18 C19 C20 120.3(3) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C19 C20 C21 121.5(3) . .
C19 C20 H20 119.3 . .
C21 C20 H20 119.3 . .
C20 C21 C16 117.0(3) . .
C20 C21 C22 120.5(3) . .
C16 C21 C22 122.5(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C17 C23 H23A 109.5 . .
C17 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C17 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
F1 B1 F2 108.5(3) . .
F1 B1 N2 111.8(3) . .
F2 B1 N2 111.3(3) . .
F1 B1 N1 110.2(3) . .
F2 B1 N1 107.8(3) . .
N2 B1 N1 107.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.731(3) .
S1 C1 1.736(3) .
F1 B1 1.378(4) .
F2 B1 1.392(4) .
N1 C7 1.342(3) .
N1 C6 1.410(3) .
N1 B1 1.563(4) .
N2 C9 1.345(3) .
N2 C16 1.456(3) .
N2 B1 1.539(4) .
C1 C2 1.384(4) .
C1 C6 1.403(4) .
C2 C3 1.374(5) .
C2 H2 0.9300 .
C3 C4 1.388(5) .
C3 H3 0.9300 .
C4 C5 1.384(4) .
C4 H4 0.9300 .
C5 C6 1.386(4) .
C5 H5 0.9300 .
C7 C8 1.387(4) .
C8 C9 1.387(4) .
C8 H8 0.9300 .
C9 C10 1.495(4) .
C10 C11 1.384(4) .
C10 C15 1.393(4) .
C11 C12 1.386(4) .
C11 H11 0.9300 .
C12 C13 1.379(5) .
C12 H12 0.9300 .
C13 C14 1.362(5) .
C13 H13 0.9300 .
C14 C15 1.387(4) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.394(4) .
C16 C21 1.397(4) .
C17 C18 1.380(4) .
C17 C23 1.519(4) .
C18 C19 1.371(4) .
C18 H18 0.9300 .
C19 C20 1.371(4) .
C19 H19 0.9300 .
C20 C21 1.390(4) .
C20 H20 0.9300 .
C21 C22 1.486(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
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
C7 S1 C1 C2 -179.4(3) . . . .
C7 S1 C1 C6 0.6(2) . . . .
C6 C1 C2 C3 0.2(5) . . . .
S1 C1 C2 C3 -179.8(2) . . . .
C1 C2 C3 C4 -0.4(5) . . . .
C2 C3 C4 C5 0.4(5) . . . .
C3 C4 C5 C6 -0.2(5) . . . .
C4 C5 C6 C1 -0.1(5) . . . .
C4 C5 C6 N1 -179.6(3) . . . .
C2 C1 C6 C5 0.1(5) . . . .
S1 C1 C6 C5 -179.9(2) . . . .
C2 C1 C6 N1 179.7(3) . . . .
S1 C1 C6 N1 -0.3(3) . . . .
C7 N1 C6 C5 179.3(3) . . . .
B1 N1 C6 C5 8.0(5) . . . .
C7 N1 C6 C1 -0.2(3) . . . .
B1 N1 C6 C1 -171.6(3) . . . .
C6 N1 C7 C8 178.7(3) . . . .
B1 N1 C7 C8 -9.3(4) . . . .
C6 N1 C7 S1 0.7(3) . . . .
B1 N1 C7 S1 172.7(2) . . . .
C1 S1 C7 N1 -0.8(2) . . . .
C1 S1 C7 C8 -178.7(3) . . . .
N1 C7 C8 C9 -9.0(4) . . . .
S1 C7 C8 C9 168.8(2) . . . .
C16 N2 C9 C8 -167.4(3) . . . .
B1 N2 C9 C8 16.0(4) . . . .
C16 N2 C9 C10 13.1(4) . . . .
B1 N2 C9 C10 -163.5(3) . . . .
C7 C8 C9 N2 5.8(4) . . . .
C7 C8 C9 C10 -174.7(3) . . . .
N2 C9 C10 C11 126.4(3) . . . .
C8 C9 C10 C11 -53.0(4) . . . .
N2 C9 C10 C15 -53.3(4) . . . .
C8 C9 C10 C15 127.2(3) . . . .
C15 C10 C11 C12 2.1(5) . . . .
C9 C10 C11 C12 -177.6(3) . . . .
C10 C11 C12 C13 -1.3(5) . . . .
C11 C12 C13 C14 -0.4(6) . . . .
C12 C13 C14 C15 1.3(6) . . . .
C13 C14 C15 C10 -0.5(5) . . . .
C11 C10 C15 C14 -1.2(4) . . . .
C9 C10 C15 C14 178.5(3) . . . .
C9 N2 C16 C17 99.1(3) . . . .
B1 N2 C16 C17 -84.2(3) . . . .
C9 N2 C16 C21 -80.6(3) . . . .
B1 N2 C16 C21 96.2(3) . . . .
C21 C16 C17 C18 -2.2(4) . . . .
N2 C16 C17 C18 178.2(3) . . . .
C21 C16 C17 C23 173.1(3) . . . .
N2 C16 C17 C23 -6.6(4) . . . .
C16 C17 C18 C19 2.0(5) . . . .
C23 C17 C18 C19 -173.3(3) . . . .
C17 C18 C19 C20 -0.7(5) . . . .
C18 C19 C20 C21 -0.4(5) . . . .
C19 C20 C21 C16 0.2(4) . . . .
C19 C20 C21 C22 178.0(3) . . . .
C17 C16 C21 C20 1.1(4) . . . .
N2 C16 C21 C20 -179.3(2) . . . .
C17 C16 C21 C22 -176.6(3) . . . .
N2 C16 C21 C22 3.0(4) . . . .
C9 N2 B1 F1 -151.1(3) . . . .
C16 N2 B1 F1 32.2(4) . . . .
C9 N2 B1 F2 87.5(3) . . . .
C16 N2 B1 F2 -89.2(3) . . . .
C9 N2 B1 N1 -30.1(4) . . . .
C16 N2 B1 N1 153.2(2) . . . .
C7 N1 B1 F1 148.2(3) . . . .
C6 N1 B1 F1 -41.0(4) . . . .
C7 N1 B1 F2 -93.6(3) . . . .
C6 N1 B1 F2 77.2(4) . . . .
C7 N1 B1 N2 26.3(4) . . . .
C6 N1 B1 N2 -162.9(2) . . . .
