#------------------------------------------------------------------------------
#$Date: 2019-10-08 12:40:47 +0300 (Tue, 08 Oct 2019) $
#$Revision: 219163 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234477.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_7234477
loop_
_publ_author_name
'Karattu Chali Naeem'
'Akhila Subhakumari'
'Sunil Varughese'
'Vijayakumar C. Nair'
_publ_section_title
;
 Heteroatom induced contrasting effects on the stimuli responsive
 properties of anthracene based donor-pi-acceptor fluorophores
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10225
_journal_page_last               10231
_journal_paper_doi               10.1039/C5TC02062J
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C23 H15 N S'
_chemical_formula_sum            'C23 H15 N S'
_chemical_formula_weight         337.42
_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
_cell_angle_alpha                90
_cell_angle_beta                 107.08(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.853(14)
_cell_length_b                   14.006(19)
_cell_length_c                   12.99(2)
_cell_measurement_reflns_used    2975
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.1
_cell_volume                     1714(4)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12541
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.241
_diffrn_reflns_theta_min         3.340
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.733
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       Block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.120
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0811
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1333P)²+0.3371P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2107
_refine_ls_wR_factor_ref         0.2467
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2651
_reflns_number_total             3390
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            J-Mater-Chem-C-2015-3-10225.cif
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7234477
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.962
_shelx_estimated_absorpt_t_max   0.962
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.5481(3) 0.0550(2) 0.2237(3) 0.0420(7) Uani 1 1 d . . . . .
C4 C 0.4155(3) -0.0570(2) 0.0838(3) 0.0425(7) Uani 1 1 d . . . . .
C5 C 0.3474(3) 0.0300(2) 0.0932(3) 0.0428(7) Uani 1 1 d . . . . .
C6 C 0.2105(3) 0.0479(3) 0.0242(3) 0.0534(9) Uani 1 1 d . . . . .
H6 H 0.1643 0.1049 0.0287 0.064 Uiso 1 1 calc R U . . .
C7 C 0.1457(3) -0.0209(3) -0.0507(3) 0.0557(9) Uani 1 1 d . . . . .
H7 H 0.0544 -0.0102 -0.0958 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2148(4) -0.1060(3) -0.0597(3) 0.0556(9) Uani 1 1 d . . . . .
H8 H 0.1695 -0.1505 -0.1116 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3490(4) -0.1257(2) 0.0068(3) 0.0512(9) Uani 1 1 d . . . . .
H9 H 0.3942 -0.1828 0.0008 0.061 Uiso 1 1 calc R U . . .
C10 C 0.6522(3) 0.1026(2) 0.3117(3) 0.0466(8) Uani 1 1 d . . . . .
H10 H 0.6278 0.1613 0.3348 0.056 Uiso 1 1 calc R U . . .
C11 C 0.7800(3) 0.0677(2) 0.3613(3) 0.0468(8) Uani 1 1 d . . . . .
H11 H 0.8037 0.0101 0.3352 0.056 Uiso 1 1 calc R U . . .
C12 C 0.8888(3) 0.1105(2) 0.4537(3) 0.0414(7) Uani 1 1 d . . . . .
C13 C 1.0633(4) 0.1024(3) 0.3469(3) 0.0539(9) Uani 1 1 d . . . . .
H13 H 0.9952 0.0753 0.2889 0.065 Uiso 1 1 calc R U . . .
C14 C 1.1958(4) 0.1193(3) 0.3390(4) 0.0680(12) Uani 1 1 d . . . . .
H14 H 1.2174 0.1024 0.2763 0.082 Uiso 1 1 calc R U . . .
C15 C 1.2998(4) 0.1618(3) 0.4236(4) 0.0737(13) Uani 1 1 d . . . . .
H15 H 1.3889 0.1745 0.4158 0.088 Uiso 1 1 calc R U . . .
C16 C 1.2725(4) 0.1848(3) 0.5170(4) 0.0649(11) Uani 1 1 d . . . . .
H16 H 1.3432 0.2129 0.5724 0.078 Uiso 1 1 calc R U . . .
C17 C 1.1064(3) 0.1845(2) 0.6284(3) 0.0513(9) Uani 1 1 d . . . . .
H17 H 1.1773 0.2106 0.6853 0.062 Uiso 1 1 calc R U . . .
C18 C 0.9488(5) 0.1766(3) 0.7445(3) 0.0613(10) Uani 1 1 d . . . . .
H18 H 1.0223 0.1975 0.8030 0.074 Uiso 1 1 calc R U . . .
C19 C 0.8200(5) 0.1582(3) 0.7578(4) 0.0713(12) Uani 1 1 d . . . . .
H19 H 0.8062 0.1663 0.8250 0.086 Uiso 1 1 calc R U . . .
C20 C 0.7069(5) 0.1268(3) 0.6701(4) 0.0703(12) Uani 1 1 d . . . . .
H20 H 0.6179 0.1168 0.6794 0.084 Uiso 1 1 calc R U . . .
C21 C 0.7263(4) 0.1108(3) 0.5716(3) 0.0562(9) Uani 1 1 d . . . . .
H21 H 0.6517 0.0870 0.5157 0.067 Uiso 1 1 calc R U . . .
C22 C 0.8607(3) 0.1302(2) 0.5531(3) 0.0432(7) Uani 1 1 d . . . . .
C23 C 0.9739(4) 0.1647(2) 0.6424(3) 0.0471(8) Uani 1 1 d . . . . .
C24 C 1.0263(3) 0.1255(2) 0.4433(3) 0.0417(7) Uani 1 1 d . . . . .
C25 C 1.1349(3) 0.1661(2) 0.5318(3) 0.0467(8) Uani 1 1 d . . . . .
N1 N 0.4248(3) 0.0921(2) 0.1727(2) 0.0457(7) Uani 1 1 d . . . . .
S3 S 0.58066(8) -0.05986(6) 0.17917(7) 0.0477(3) 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'
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
N1 C2 C10 123.5(3) . .
N1 C2 S3 115.2(2) . .
C10 C2 S3 121.3(2) . .
C9 C4 C5 121.2(3) . .
C9 C4 S3 129.6(3) . .
C5 C4 S3 109.2(2) . .
N1 C5 C6 125.1(3) . .
N1 C5 C4 115.6(3) . .
C6 C5 C4 119.3(3) . .
C7 C6 C5 118.8(3) . .
C7 C6 H6 120.6 . .
C5 C6 H6 120.6 . .
C6 C7 C8 121.2(3) . .
C6 C7 H7 119.4 . .
C8 C7 H7 119.4 . .
C9 C8 C7 121.4(3) . .
C9 C8 H8 119.3 . .
C7 C8 H8 119.3 . .
C8 C9 C4 118.1(3) . .
C8 C9 H9 120.9 . .
C4 C9 H9 120.9 . .
C11 C10 C2 124.2(3) . .
C11 C10 H10 117.9 . .
C2 C10 H10 117.9 . .
C10 C11 C12 127.0(3) . .
C10 C11 H11 116.5 . .
C12 C11 H11 116.5 . .
C24 C12 C22 120.3(3) . .
C24 C12 C11 117.9(3) . .
C22 C12 C11 121.7(3) . .
C14 C13 C24 121.3(4) . .
C14 C13 H13 119.3 . .
C24 C13 H13 119.3 . .
C13 C14 C15 120.9(4) . .
C13 C14 H14 119.6 . .
C15 C14 H14 119.6 . .
C16 C15 C14 120.8(4) . .
C16 C15 H15 119.6 . .
C14 C15 H15 119.6 . .
C15 C16 C25 121.0(4) . .
C15 C16 H16 119.5 . .
C25 C16 H16 119.5 . .
C25 C17 C23 121.7(3) . .
C25 C17 H17 119.2 . .
C23 C17 H17 119.2 . .
C19 C18 C23 121.3(4) . .
C19 C18 H18 119.3 . .
C23 C18 H18 119.3 . .
C18 C19 C20 120.3(4) . .
C18 C19 H19 119.8 . .
C20 C19 H19 119.8 . .
C21 C20 C19 120.8(4) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C20 C21 C22 121.0(4) . .
C20 C21 H21 119.5 . .
C22 C21 H21 119.5 . .
C12 C22 C23 119.1(3) . .
C12 C22 C21 123.2(3) . .
C23 C22 C21 117.6(3) . .
C17 C23 C18 121.4(3) . .
C17 C23 C22 119.7(3) . .
C18 C23 C22 119.0(3) . .
C12 C24 C25 119.3(3) . .
C12 C24 C13 122.9(3) . .
C25 C24 C13 117.8(3) . .
C17 C25 C24 119.7(3) . .
C17 C25 C16 122.2(3) . .
C24 C25 C16 118.1(4) . .
C2 N1 C5 110.6(3) . .
C4 S3 C2 89.45(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.309(4) .
C2 C10 1.454(5) .
C2 S3 1.770(4) .
C4 C9 1.404(5) .
C4 C5 1.413(5) .
C4 S3 1.732(4) .
C5 N1 1.393(4) .
C5 C6 1.406(5) .
C6 C7 1.385(5) .
C6 H6 0.9300 .
C7 C8 1.395(6) .
C7 H7 0.9300 .
C8 C9 1.378(5) .
C8 H8 0.9300 .
C9 H9 0.9300 .
C10 C11 1.328(5) .
C10 H10 0.9300 .
C11 C12 1.481(5) .
C11 H11 0.9300 .
C12 C24 1.417(5) .
C12 C22 1.424(5) .
C13 C14 1.360(5) .
C13 C24 1.440(5) .
C13 H13 0.9300 .
C14 C15 1.396(6) .
C14 H14 0.9300 .
C15 C16 1.356(7) .
C15 H15 0.9300 .
C16 C25 1.448(5) .
C16 H16 0.9300 .
C17 C25 1.388(5) .
C17 C23 1.398(5) .
C17 H17 0.9300 .
C18 C19 1.354(6) .
C18 C23 1.429(6) .
C18 H18 0.9300 .
C19 C20 1.410(7) .
C19 H19 0.9300 .
C20 C21 1.367(6) .
C20 H20 0.9300 .
C21 C22 1.439(5) .
C21 H21 0.9300 .
C22 C23 1.436(5) .
C24 C25 1.437(5) .
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
C9 C4 C5 N1 -179.9(3) . . . .
S3 C4 C5 N1 0.6(3) . . . .
C9 C4 C5 C6 0.0(5) . . . .
S3 C4 C5 C6 -179.4(2) . . . .
N1 C5 C6 C7 -179.5(3) . . . .
C4 C5 C6 C7 0.6(5) . . . .
C5 C6 C7 C8 -1.2(5) . . . .
C6 C7 C8 C9 1.2(5) . . . .
C7 C8 C9 C4 -0.6(5) . . . .
C5 C4 C9 C8 -0.1(5) . . . .
S3 C4 C9 C8 179.3(3) . . . .
N1 C2 C10 C11 -177.1(3) . . . .
S3 C2 C10 C11 3.6(5) . . . .
C2 C10 C11 C12 -177.6(3) . . . .
C10 C11 C12 C24 -125.9(4) . . . .
C10 C11 C12 C22 58.3(5) . . . .
C24 C13 C14 C15 -1.4(6) . . . .
C13 C14 C15 C16 1.9(7) . . . .
C14 C15 C16 C25 -0.1(7) . . . .
C23 C18 C19 C20 -0.2(6) . . . .
C18 C19 C20 C21 2.6(6) . . . .
C19 C20 C21 C22 -3.2(6) . . . .
C24 C12 C22 C23 -0.5(4) . . . .
C11 C12 C22 C23 175.1(3) . . . .
C24 C12 C22 C21 -175.9(3) . . . .
C11 C12 C22 C21 -0.2(5) . . . .
C20 C21 C22 C12 176.8(3) . . . .
C20 C21 C22 C23 1.4(5) . . . .
C25 C17 C23 C18 175.0(3) . . . .
C25 C17 C23 C22 -4.1(5) . . . .
C19 C18 C23 C17 179.4(3) . . . .
C19 C18 C23 C22 -1.5(5) . . . .
C12 C22 C23 C17 4.3(4) . . . .
C21 C22 C23 C17 180.0(3) . . . .
C12 C22 C23 C18 -174.7(3) . . . .
C21 C22 C23 C18 0.9(4) . . . .
C22 C12 C24 C25 -3.6(4) . . . .
C11 C12 C24 C25 -179.4(3) . . . .
C22 C12 C24 C13 176.7(3) . . . .
C11 C12 C24 C13 0.9(4) . . . .
C14 C13 C24 C12 178.9(3) . . . .
C14 C13 C24 C25 -0.8(5) . . . .
C23 C17 C25 C24 -0.1(5) . . . .
C23 C17 C25 C16 -178.9(3) . . . .
C12 C24 C25 C17 3.9(4) . . . .
C13 C24 C25 C17 -176.3(3) . . . .
C12 C24 C25 C16 -177.2(3) . . . .
C13 C24 C25 C16 2.5(5) . . . .
C15 C16 C25 C17 176.7(4) . . . .
C15 C16 C25 C24 -2.1(6) . . . .
C10 C2 N1 C5 -179.4(3) . . . .
S3 C2 N1 C5 -0.1(3) . . . .
C6 C5 N1 C2 179.7(3) . . . .
C4 C5 N1 C2 -0.3(4) . . . .
C9 C4 S3 C2 -179.9(3) . . . .
C5 C4 S3 C2 -0.6(2) . . . .
N1 C2 S3 C4 0.4(3) . . . .
C10 C2 S3 C4 179.8(3) . . . .
