#------------------------------------------------------------------------------
#$Date: 2017-08-09 05:02:29 +0300 (Wed, 09 Aug 2017) $
#$Revision: 199654 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228871.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_7228871
loop_
_publ_author_name
'Niu , Yahui'
'Xu, Longfei'
'Wang, Qin'
'Wu, Haoran'
'Zhang, Yanrong'
_publ_section_title
;
 Planar 2-(2-hydroxyphenyl)benzothiazole-based dyes functionalized via
 triple bonds as exceedingly efficient solid-state fluorophores
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01108C
_journal_year                    2017
_chemical_formula_sum            'C21 H13 N O S'
_chemical_formula_weight         327.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-07-26 deposited with the CCDC.
2017-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.5363(4)
_cell_length_b                   10.1250(8)
_cell_length_c                   34.375(3)
_cell_measurement_reflns_used    1677
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      21.307
_cell_measurement_theta_min      2.336
_cell_volume                     1578.8(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0621
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8041
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.211
_exptl_absorpt_correction_T_max  0.9690
_exptl_absorpt_correction_T_min  0.9147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.10(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0446
_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)+(0.0131P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                2007
_reflns_number_total             2782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7ce01108c2.cif
_cod_data_source_block           160507b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7228871
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
N1 N 0.6274(5) 0.4016(2) 0.05772(5) 0.0430(6) Uani 1 1 d .
O1 O 0.2692(5) 0.54461(17) 0.01592(4) 0.0613(6) Uani 1 1 d .
H1 H 0.3864 0.4851 0.0207 0.092 Uiso 1 1 calc R
S1 S 0.67885(18) 0.41454(7) 0.132004(17) 0.0533(2) Uani 1 1 d .
C1 C 0.5353(6) 0.4679(2) 0.08764(7) 0.0417(7) Uani 1 1 d .
C2 C 0.8209(7) 0.3037(3) 0.06813(7) 0.0450(7) Uani 1 1 d .
C3 C 0.8773(7) 0.2945(3) 0.10778(7) 0.0451(8) Uani 1 1 d .
C4 C 1.0651(7) 0.2000(3) 0.12248(8) 0.0590(9) Uani 1 1 d .
H4 H 1.0997 0.1939 0.1491 0.071 Uiso 1 1 calc R
C5 C 1.1995(7) 0.1152(3) 0.09707(8) 0.0615(8) Uani 1 1 d .
H5 H 1.3267 0.0507 0.1065 0.074 Uiso 1 1 calc R
C6 C 1.1485(7) 0.1239(3) 0.05737(8) 0.0611(8) Uani 1 1 d .
H6 H 1.2428 0.0658 0.0405 0.073 Uiso 1 1 calc R
C7 C 0.9609(7) 0.2173(3) 0.04273(8) 0.0526(8) Uani 1 1 d .
H7 H 0.9275 0.2229 0.0161 0.063 Uiso 1 1 calc R
C8 C 0.3295(6) 0.5765(2) 0.08481(6) 0.0396(6) Uani 1 1 d .
C9 C 0.2048(7) 0.6096(2) 0.04879(7) 0.0447(7) Uani 1 1 d .
C10 C 0.0070(7) 0.7127(3) 0.04616(8) 0.0536(8) Uani 1 1 d .
H10 H -0.0756 0.7344 0.0222 0.064 Uiso 1 1 calc R
C11 C -0.0678(7) 0.7829(3) 0.07860(8) 0.0522(8) Uani 1 1 d .
H11 H -0.2013 0.8523 0.0764 0.063 Uiso 1 1 calc R
C12 C 0.0506(7) 0.7532(3) 0.11468(8) 0.0471(8) Uani 1 1 d .
C13 C 0.2513(7) 0.6510(3) 0.11703(7) 0.0479(8) Uani 1 1 d .
H13 H 0.3366 0.6315 0.1410 0.058 Uiso 1 1 calc R
C14 C -0.0312(7) 0.8269(3) 0.14833(8) 0.0564(9) Uani 1 1 d .
C15 C -0.1052(7) 0.8903(3) 0.17573(8) 0.0575(9) Uani 1 1 d .
C16 C -0.1957(8) 0.9732(3) 0.20701(7) 0.0502(8) Uani 1 1 d .
C17 C -0.0874(8) 0.9577(3) 0.24402(8) 0.0724(12) Uani 1 1 d .
H17 H 0.0471 0.8908 0.2493 0.087 Uiso 1 1 calc R
C18 C -0.1775(9) 1.0411(3) 0.27320(8) 0.0805(11) Uani 1 1 d .
H18 H -0.1049 1.0289 0.2982 0.097 Uiso 1 1 calc R
C19 C -0.3675(8) 1.1394(3) 0.26638(9) 0.0708(10) Uani 1 1 d .
H19 H -0.4275 1.1948 0.2865 0.085 Uiso 1 1 calc R
C20 C -0.4712(8) 1.1573(3) 0.22994(10) 0.0874(12) Uani 1 1 d .
H20 H -0.5993 1.2268 0.2248 0.105 Uiso 1 1 calc R
C21 C -0.3887(8) 1.0735(3) 0.20040(8) 0.0751(11) Uani 1 1 d .
H21 H -0.4659 1.0856 0.1756 0.090 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'
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
C1 N1 C2 111.9(2)
C9 O1 H1 109.5
C3 S1 C1 89.48(13)
N1 C1 C8 123.3(2)
N1 C1 S1 114.4(2)
C8 C1 S1 122.37(19)
N1 C2 C7 125.7(2)
N1 C2 C3 114.9(2)
C7 C2 C3 119.4(3)
C4 C3 C2 121.3(3)
C4 C3 S1 129.4(2)
C2 C3 S1 109.3(2)
C5 C4 C3 118.5(3)
C5 C4 H4 120.7
C3 C4 H4 120.7
C4 C5 C6 120.9(3)
C4 C5 H5 119.5
C6 C5 H5 119.5
C7 C6 C5 120.7(3)
C7 C6 H6 119.7
C5 C6 H6 119.7
C6 C7 C2 119.2(3)
C6 C7 H7 120.4
C2 C7 H7 120.4
C13 C8 C9 118.2(3)
C13 C8 C1 121.7(2)
C9 C8 C1 120.1(2)
O1 C9 C10 117.3(2)
O1 C9 C8 122.7(3)
C10 C9 C8 120.1(2)
C11 C10 C9 120.1(3)
C11 C10 H10 119.9
C9 C10 H10 119.9
C10 C11 C12 121.5(3)
C10 C11 H11 119.3
C12 C11 H11 119.3
C13 C12 C11 118.1(2)
C13 C12 C14 121.1(3)
C11 C12 C14 120.8(3)
C12 C13 C8 122.0(2)
C12 C13 H13 119.0
C8 C13 H13 119.0
C15 C14 C12 178.0(3)
C14 C15 C16 176.5(3)
C21 C16 C17 118.0(3)
C21 C16 C15 119.9(3)
C17 C16 C15 122.0(3)
C16 C17 C18 120.0(3)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 121.4(3)
C19 C18 H18 119.3
C17 C18 H18 119.3
C18 C19 C20 119.1(3)
C18 C19 H19 120.4
C20 C19 H19 120.4
C19 C20 C21 120.5(3)
C19 C20 H20 119.7
C21 C20 H20 119.7
C16 C21 C20 120.8(3)
C16 C21 H21 119.6
C20 C21 H21 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.297(3)
N1 C2 1.372(3)
O1 C9 1.340(2)
O1 H1 0.8200
S1 C3 1.726(3)
S1 C1 1.744(3)
C1 C8 1.446(3)
C2 C7 1.389(3)
C2 C3 1.390(3)
C3 C4 1.377(3)
C4 C5 1.368(3)
C4 H4 0.9300
C5 C6 1.387(3)
C5 H5 0.9300
C6 C7 1.368(4)
C6 H6 0.9300
C7 H7 0.9300
C8 C13 1.386(3)
C8 C9 1.402(3)
C9 C10 1.379(4)
C10 C11 1.365(3)
C10 H10 0.9300
C11 C12 1.384(3)
C11 H11 0.9300
C12 C13 1.381(3)
C12 C14 1.426(3)
C13 H13 0.9300
C14 C15 1.188(3)
C15 C16 1.424(3)
C16 C21 1.361(4)
C16 C17 1.373(3)
C17 C18 1.373(4)
C17 H17 0.9300
C18 C19 1.338(4)
C18 H18 0.9300
C19 C20 1.350(4)
C19 H19 0.9300
C20 C21 1.375(3)
C20 H20 0.9300
C21 H21 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
C2 N1 C1 C8 -180.0(2)
C2 N1 C1 S1 -0.3(3)
C3 S1 C1 N1 0.1(2)
C3 S1 C1 C8 179.8(2)
C1 N1 C2 C7 -179.0(3)
C1 N1 C2 C3 0.4(3)
N1 C2 C3 C4 179.4(2)
C7 C2 C3 C4 -1.2(4)
N1 C2 C3 S1 -0.3(3)
C7 C2 C3 S1 179.1(2)
C1 S1 C3 C4 -179.5(3)
C1 S1 C3 C2 0.1(2)
C2 C3 C4 C5 0.7(4)
S1 C3 C4 C5 -179.7(2)
C3 C4 C5 C6 0.1(4)
C4 C5 C6 C7 -0.4(5)
C5 C6 C7 C2 -0.1(4)
N1 C2 C7 C6 -179.8(3)
C3 C2 C7 C6 0.8(4)
N1 C1 C8 C13 -175.5(3)
S1 C1 C8 C13 4.9(4)
N1 C1 C8 C9 4.1(4)
S1 C1 C8 C9 -175.6(2)
C13 C8 C9 O1 179.2(2)
C1 C8 C9 O1 -0.4(4)
C13 C8 C9 C10 -0.9(4)
C1 C8 C9 C10 179.5(3)
O1 C9 C10 C11 -180.0(2)
C8 C9 C10 C11 0.1(4)
C9 C10 C11 C12 -0.1(4)
C10 C11 C12 C13 0.9(4)
C10 C11 C12 C14 -179.6(3)
C11 C12 C13 C8 -1.7(4)
C14 C12 C13 C8 178.7(3)
C9 C8 C13 C12 1.7(4)
C1 C8 C13 C12 -178.7(2)
C13 C12 C14 C15 -176(100)
C11 C12 C14 C15 4(10)
C12 C14 C15 C16 -37(14)
C14 C15 C16 C21 32(6)
C14 C15 C16 C17 -146(6)
C21 C16 C17 C18 0.9(5)
C15 C16 C17 C18 179.1(3)
C16 C17 C18 C19 -0.9(6)
C17 C18 C19 C20 -0.4(6)
C18 C19 C20 C21 1.7(6)
C17 C16 C21 C20 0.4(5)
C15 C16 C21 C20 -177.8(3)
C19 C20 C21 C16 -1.7(6)
