#------------------------------------------------------------------------------
#$Date: 2020-11-21 00:28:57 +0200 (Sat, 21 Nov 2020) $
#$Revision: 259205 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/82/4518256.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_4518256
loop_
_publ_author_name
'Chen, Yahui'
'Fang, Yu'
'Gu, Hao'
'Qiang, Jian'
'Li, Haidong'
'Fan, Jiangli'
'Cao, Jianfang'
'Wang, Fang'
'Lu, Sheng'
'Chen, Xiaoqiang'
_publ_section_title
;
 Color-Tunable and ESIPT-Inspired Solid Fluorophores Based on
 Benzothiazole Derivatives: Aggregation-Induced Emission, Strong
 Solvatochromic Effect, and White Light Emission
;
_journal_name_full               'ACS Applied Materials & Interfaces'
_journal_paper_doi               10.1021/acsami.0c16585
_journal_year                    2020
_chemical_formula_moiety         'C16 H13 N O2 S'
_chemical_formula_sum            'C16 H13 N O2 S'
_chemical_formula_weight         283.33
_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                 102.852(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.2703(14)
_cell_length_b                   23.841(5)
_cell_length_c                   7.9637(15)
_cell_measurement_reflns_used    4489
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.76
_cell_volume                     1345.8(5)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       'ω scans'
_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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9446
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.71
_exptl_absorpt_coefficient_mu    0.240
_exptl_absorpt_correction_T_max  0.9535
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rodlike
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.059
_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     183
_refine_ls_number_reflns         2373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0407
_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)+(0.0635P)²+0.5742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2116
_reflns_number_total             2373
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            am0c16585_si_006.cif
_cod_data_source_block           a1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4518256
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 0.14513(7) 0.56310(2) 0.33159(6) 0.04202(19) Uani 1 1 d . . .
C1 C 0.2675(3) 0.59049(7) 0.6476(2) 0.0374(4) Uani 1 1 d . . .
C9 C 0.2025(2) 0.42990(8) 0.2878(2) 0.0356(4) Uani 1 1 d . . .
C8 C 0.2589(2) 0.45317(8) 0.4520(2) 0.0331(4) Uani 1 1 d . . .
C13 C 0.3327(3) 0.41711(8) 0.5892(2) 0.0373(4) Uani 1 1 d . . .
H4 H 0.3717 0.4322 0.6991 0.045 Uiso 1 1 calc R . .
C7 C 0.2425(2) 0.51341(7) 0.4888(2) 0.0333(4) Uani 1 1 d . . .
C10 C 0.2128(3) 0.37209(8) 0.2641(2) 0.0416(4) Uani 1 1 d . . .
C12 C 0.3499(3) 0.35993(8) 0.5681(2) 0.0413(4) Uani 1 1 d . . .
C6 C 0.1846(3) 0.61460(8) 0.4884(3) 0.0409(4) Uani 1 1 d . . .
C11 C 0.2870(3) 0.33784(8) 0.4044(3) 0.0445(5) Uani 1 1 d . . .
H9 H 0.2946 0.2994 0.3879 0.053 Uiso 1 1 calc R . .
C2 C 0.3127(3) 0.62445(9) 0.7945(3) 0.0473(5) Uani 1 1 d . . .
H10 H 0.3673 0.6091 0.9013 0.057 Uiso 1 1 calc R . .
C5 C 0.1436(3) 0.67174(9) 0.4740(3) 0.0506(5) Uani 1 1 d . . .
H11 H 0.0862 0.6874 0.3684 0.061 Uiso 1 1 calc R . .
C3 C 0.2747(3) 0.68095(9) 0.7781(3) 0.0530(5) Uani 1 1 d . . .
H12 H 0.3060 0.7039 0.8746 0.064 Uiso 1 1 calc R . .
C15 C 0.2629(3) 0.47726(10) 0.0447(3) 0.0530(5) Uani 1 1 d . . .
H13A H 0.3776 0.4914 0.1162 0.080 Uiso 1 1 calc R . .
H13B H 0.2094 0.5051 -0.0390 0.080 Uiso 1 1 calc R . .
H13C H 0.2895 0.4439 -0.0133 0.080 Uiso 1 1 calc R . .
C14 C 0.4327(4) 0.32289(9) 0.7203(3) 0.0597(6) Uani 1 1 d . . .
H14A H 0.5620 0.3332 0.7654 0.090 Uiso 1 1 calc R . .
H14B H 0.4264 0.2844 0.6841 0.090 Uiso 1 1 calc R . .
H14C H 0.3624 0.3276 0.8080 0.090 Uiso 1 1 calc R . .
C4 C 0.1902(3) 0.70423(9) 0.6195(3) 0.0564(6) Uani 1 1 d . . .
H15 H 0.1648 0.7425 0.6120 0.068 Uiso 1 1 calc R . .
C16 C 0.1376(3) 0.34684(10) 0.0920(3) 0.0596(6) Uani 1 1 d . . .
H16 H 0.0712 0.3704 0.0067 0.072 Uiso 1 1 calc R . .
N1 N 0.2983(2) 0.53322(6) 0.64412(19) 0.0378(4) Uani 1 1 d . . .
O1 O 0.13110(18) 0.46427(6) 0.14984(16) 0.0424(3) Uani 1 1 d . . .
O2 O 0.1543(3) 0.29982(9) 0.0539(3) 0.0912(6) 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'
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'
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
_geom_angle_publ_flag
C6 S1 C7 89.34(9) . . ?
N1 C1 C2 125.30(17) . . ?
N1 C1 C6 115.19(16) . . ?
C2 C1 C6 119.51(17) . . ?
O1 C9 C8 119.43(16) . . ?
O1 C9 C10 120.12(16) . . ?
C8 C9 C10 120.42(17) . . ?
C9 C8 C13 117.97(17) . . ?
C9 C8 C7 123.58(16) . . ?
C13 C8 C7 118.45(16) . . ?
C12 C13 C8 122.66(17) . . ?
C12 C13 H4 118.7 . . ?
C8 C13 H4 118.7 . . ?
N1 C7 C8 121.32(16) . . ?
N1 C7 S1 115.09(13) . . ?
C8 C7 S1 123.58(13) . . ?
C11 C10 C9 119.56(17) . . ?
C11 C10 C16 120.01(19) . . ?
C9 C10 C16 120.38(19) . . ?
C13 C12 C11 117.99(18) . . ?
C13 C12 C14 120.58(18) . . ?
C11 C12 C14 121.42(18) . . ?
C5 C6 C1 121.13(19) . . ?
C5 C6 S1 129.54(16) . . ?
C1 C6 S1 109.33(14) . . ?
C12 C11 C10 121.33(18) . . ?
C12 C11 H9 119.3 . . ?
C10 C11 H9 119.3 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H10 120.6 . . ?
C1 C2 H10 120.6 . . ?
C4 C5 C6 118.3(2) . . ?
C4 C5 H11 120.9 . . ?
C6 C5 H11 120.9 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H12 119.5 . . ?
C4 C3 H12 119.5 . . ?
O1 C15 H13A 109.5 . . ?
O1 C15 H13B 109.5 . . ?
H13A C15 H13B 109.5 . . ?
O1 C15 H13C 109.5 . . ?
H13A C15 H13C 109.5 . . ?
H13B C15 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H15 119.4 . . ?
C3 C4 H15 119.4 . . ?
O2 C16 C10 126.0(3) . . ?
O2 C16 H16 117.0 . . ?
C10 C16 H16 117.0 . . ?
C7 N1 C1 111.05(15) . . ?
C9 O1 C15 114.26(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.729(2) . ?
S1 C7 1.7542(18) . ?
C1 N1 1.385(2) . ?
C1 C2 1.400(3) . ?
C1 C6 1.401(3) . ?
C9 O1 1.376(2) . ?
C9 C8 1.395(2) . ?
C9 C10 1.396(3) . ?
C8 C13 1.400(3) . ?
C8 C7 1.476(3) . ?
C13 C12 1.383(3) . ?
C13 H4 0.9300 . ?
C7 N1 1.302(2) . ?
C10 C11 1.392(3) . ?
C10 C16 1.485(3) . ?
C12 C11 1.386(3) . ?
C12 C14 1.512(3) . ?
C6 C5 1.394(3) . ?
C11 H9 0.9300 . ?
C2 C3 1.375(3) . ?
C2 H10 0.9300 . ?
C5 C4 1.373(3) . ?
C5 H11 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H12 0.9300 . ?
C15 O1 1.439(2) . ?
C15 H13A 0.9600 . ?
C15 H13B 0.9600 . ?
C15 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C4 H15 0.9300 . ?
C16 O2 1.175(3) . ?
C16 H16 0.9300 . ?
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
_geom_torsion_publ_flag
O1 C9 C8 C13 -179.35(15) . . . . ?
C10 C9 C8 C13 2.6(3) . . . . ?
O1 C9 C8 C7 1.5(3) . . . . ?
C10 C9 C8 C7 -176.54(16) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C7 C8 C13 C12 178.66(17) . . . . ?
C9 C8 C7 N1 -179.52(16) . . . . ?
C13 C8 C7 N1 1.3(3) . . . . ?
C9 C8 C7 S1 1.5(2) . . . . ?
C13 C8 C7 S1 -177.63(13) . . . . ?
C6 S1 C7 N1 0.37(15) . . . . ?
C6 S1 C7 C8 179.37(15) . . . . ?
O1 C9 C10 C11 179.36(16) . . . . ?
C8 C9 C10 C11 -2.6(3) . . . . ?
O1 C9 C10 C16 -3.3(3) . . . . ?
C8 C9 C10 C16 174.75(17) . . . . ?
C8 C13 C12 C11 -1.5(3) . . . . ?
C8 C13 C12 C14 179.29(18) . . . . ?
N1 C1 C6 C5 179.18(18) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
N1 C1 C6 S1 0.1(2) . . . . ?
C2 C1 C6 S1 179.95(14) . . . . ?
C7 S1 C6 C5 -179.3(2) . . . . ?
C7 S1 C6 C1 -0.22(14) . . . . ?
C13 C12 C11 C10 1.5(3) . . . . ?
C14 C12 C11 C10 -179.28(19) . . . . ?
C9 C10 C11 C12 0.5(3) . . . . ?
C16 C10 C11 C12 -176.88(19) . . . . ?
N1 C1 C2 C3 179.63(18) . . . . ?
C6 C1 C2 C3 -0.3(3) . . . . ?
C1 C6 C5 C4 1.3(3) . . . . ?
S1 C6 C5 C4 -179.76(17) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C11 C10 C16 O2 -10.1(4) . . . . ?
C9 C10 C16 O2 172.5(2) . . . . ?
C8 C7 N1 C1 -179.43(15) . . . . ?
S1 C7 N1 C1 -0.4(2) . . . . ?
C2 C1 N1 C7 -179.67(17) . . . . ?
C6 C1 N1 C7 0.2(2) . . . . ?
C8 C9 O1 C15 101.8(2) . . . . ?
C10 C9 O1 C15 -80.1(2) . . . . ?
