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#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/49/1514932.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_1514932
loop_
_publ_author_name
'Das, Sudipta'
'Sahana, Animesh'
'Banerjee, Arnab'
'Lohar, Sisir'
'Guha, Subarna'
'Matalobos, Jesús Sanmartín'
'Das, Debasis'
_publ_section_title
;
 Thiophene anchored naphthalene derivative: Cr3+ selective turn-on
 fluorescent probe for living cell imaging
;
_journal_issue                   8
_journal_name_full               'Analytical Methods'
_journal_page_first              2254
_journal_paper_doi               10.1039/c2ay25384d
_journal_volume                  4
_journal_year                    2012
_chemical_formula_sum            'C15 H11 N S'
_chemical_formula_weight         237.31
_space_group_IT_number           41
_symmetry_space_group_name_Hall  'A 2 -2ab'
_symmetry_space_group_name_H-M   'A b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.7541(18)
_cell_length_b                   20.966(4)
_cell_length_c                   10.5543(16)
_cell_measurement_temperature    100(2)
_cell_volume                     2379.7(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2392
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9146
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.8275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0717
_reflns_number_gt                2227
_reflns_number_total             2392
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ay25384d.txt
_cod_data_source_block           be47jea1n
_cod_database_code               1514932
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/2, y+1, z+1/2'
'x+1/2, -y+1, 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
C1 C 0.95964(16) 0.83014(8) 0.97874(16) 0.0180(4) Uani 1 1 d .
C2 C 0.98177(18) 0.77330(9) 0.91739(18) 0.0218(4) Uani 1 1 d .
H2 H 1.0545 0.7495 0.9369 0.026 Uiso 1 1 calc R
C3 C 0.89801(19) 0.75016(9) 0.8264(2) 0.0262(4) Uani 1 1 d .
H3 H 0.9156 0.7113 0.7836 0.031 Uiso 1 1 calc R
C4 C 0.79145(17) 0.78282(9) 0.79855(19) 0.0238(4) Uani 1 1 d .
H4 H 0.7368 0.7671 0.7351 0.029 Uiso 1 1 calc R
C5 C 0.76176(17) 0.83995(9) 0.86359(18) 0.0197(4) Uani 1 1 d .
C6 C 0.65008(17) 0.87346(9) 0.84037(18) 0.0220(4) Uani 1 1 d .
H6 H 0.5940 0.8582 0.7778 0.026 Uiso 1 1 calc R
C7 C 0.62168(18) 0.92727(8) 0.90644(19) 0.0232(4) Uani 1 1 d .
H7 H 0.5457 0.9489 0.8903 0.028 Uiso 1 1 calc R
C8 C 0.70447(17) 0.95119(10) 0.99884(19) 0.0221(4) Uani 1 1 d .
H8 H 0.6834 0.9885 1.0451 0.027 Uiso 1 1 calc R
C9 C 0.81500(19) 0.92084(9) 1.0222(2) 0.0200(4) Uani 1 1 d .
H9 H 0.8711 0.9380 1.0828 0.024 Uiso 1 1 calc R
C10 C 0.84625(16) 0.86390(8) 0.95646(17) 0.0168(4) Uani 1 1 d .
C11 C 1.16051(16) 0.85138(9) 1.04536(17) 0.0190(4) Uani 1 1 d .
H11 H 1.1869 0.8280 0.9731 0.023 Uiso 1 1 calc R
C12 C 1.25344(18) 0.87896(8) 1.12763(17) 0.0188(4) Uani 1 1 d .
C13 C 1.38038(17) 0.87373(9) 1.11697(19) 0.0220(4) Uani 1 1 d .
H13 H 1.4208 0.8488 1.0541 0.026 Uiso 1 1 calc R
C14 C 1.44395(17) 0.90947(9) 1.20953(19) 0.0239(4) Uani 1 1 d .
H14 H 1.5320 0.9110 1.2163 0.029 Uiso 1 1 calc R
C15 C 1.36590(18) 0.94141(10) 1.28795(18) 0.0252(5) Uani 1 1 d .
H15 H 1.3931 0.9680 1.3554 0.030 Uiso 1 1 calc R
N1 N 1.04382(14) 0.85737(7) 1.06643(14) 0.0183(3) Uani 1 1 d .
S1 S 1.21213(4) 0.92842(2) 1.25150(5) 0.02205(12) 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
C2 C1 N1 123.11(16)
C2 C1 C10 119.91(16)
N1 C1 C10 116.98(15)
C1 C2 C3 120.67(17)
C1 C2 H2 119.7
C3 C2 H2 119.7
C4 C3 C2 120.81(17)
C4 C3 H3 119.6
C2 C3 H3 119.6
C3 C4 C5 120.54(18)
C3 C4 H4 119.7
C5 C4 H4 119.7
C6 C5 C4 121.86(17)
C6 C5 C10 119.02(16)
C4 C5 C10 119.11(17)
C7 C6 C5 120.94(18)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 120.43(18)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 120.41(18)
C9 C8 H8 119.8
C7 C8 H8 119.8
C8 C9 C10 120.47(19)
C8 C9 H9 119.8
C10 C9 H9 119.8
C9 C10 C5 118.70(16)
C9 C10 C1 122.50(17)
C5 C10 C1 118.80(16)
N1 C11 C12 122.30(17)
N1 C11 H11 118.8
C12 C11 H11 118.8
C13 C12 C11 127.31(17)
C13 C12 S1 111.43(14)
C11 C12 S1 121.16(14)
C12 C13 C14 112.53(18)
C12 C13 H13 123.7
C14 C13 H13 123.7
C15 C14 C13 112.69(17)
C15 C14 H14 123.7
C13 C14 H14 123.7
C14 C15 S1 112.38(15)
C14 C15 H15 123.8
S1 C15 H15 123.8
C11 N1 C1 118.28(15)
C15 S1 C12 90.98(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.377(3)
C1 N1 1.415(2)
C1 C10 1.429(2)
C2 C3 1.403(3)
C2 H2 0.9500
C3 C4 1.367(3)
C3 H3 0.9500
C4 C5 1.417(3)
C4 H4 0.9500
C5 C6 1.413(3)
C5 C10 1.428(3)
C6 C7 1.361(3)
C6 H6 0.9500
C7 C8 1.413(3)
C7 H7 0.9500
C8 C9 1.371(3)
C8 H8 0.9500
C9 C10 1.421(3)
C9 H9 0.9500
C11 N1 1.281(2)
C11 C12 1.445(3)
C11 H11 0.9500
C12 C13 1.374(3)
C12 S1 1.7268(19)
C13 C14 1.408(3)
C13 H13 0.9500
C14 C15 1.356(3)
C14 H14 0.9500
C15 S1 1.7194(19)
C15 H15 0.9500
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
N1 C1 C2 C3 -176.66(17)
C10 C1 C2 C3 4.4(3)
C1 C2 C3 C4 -1.4(3)
C2 C3 C4 C5 -1.7(3)
C3 C4 C5 C6 -177.54(19)
C3 C4 C5 C10 1.6(3)
C4 C5 C6 C7 178.12(18)
C10 C5 C6 C7 -1.0(3)
C5 C6 C7 C8 0.8(3)
C6 C7 C8 C9 0.6(3)
C7 C8 C9 C10 -1.8(3)
C8 C9 C10 C5 1.5(3)
C8 C9 C10 C1 -179.21(17)
C6 C5 C10 C9 -0.1(3)
C4 C5 C10 C9 -179.29(16)
C6 C5 C10 C1 -179.42(16)
C4 C5 C10 C1 1.4(3)
C2 C1 C10 C9 176.34(17)
N1 C1 C10 C9 -2.7(2)
C2 C1 C10 C5 -4.4(3)
N1 C1 C10 C5 176.61(15)
N1 C11 C12 C13 177.49(18)
N1 C11 C12 S1 -6.4(3)
C11 C12 C13 C14 176.79(17)
S1 C12 C13 C14 0.3(2)
C12 C13 C14 C15 -0.4(2)
C13 C14 C15 S1 0.3(2)
C12 C11 N1 C1 178.34(15)
C2 C1 N1 C11 36.3(2)
C10 C1 N1 C11 -144.76(17)
C14 C15 S1 C12 -0.10(15)
C13 C12 S1 C15 -0.14(14)
C11 C12 S1 C15 -176.84(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 224136
