#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:47:46 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179394 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/91/4329189.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_4329189
loop_
_publ_author_name
'Arnab Banerjee'
'Animesh Sahana'
'Subarna Guha'
'Sisir Lohar'
'Ipsit Hauli'
'Subhra Kanti Mukhopadhyay'
'Jesús Sanmartín Matalobos'
'Debasis Das'
_publ_section_title
;
 Nickel(II)-Induced Excimer Formation of a Naphthalene-Based Fluorescent
 Probe for Living Cell Imaging
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5699
_journal_page_last               5704
_journal_paper_doi               10.1021/ic300130y
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C12 H11 S'
_chemical_formula_weight         187.27
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_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                90.000(5)
_cell_angle_beta                 97.512(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   17.962(5)
_cell_length_b                   5.784(5)
_cell_length_c                   9.076(5)
_cell_measurement_temperature    293(2)
_cell_volume                     934.8(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0408
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            1923
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.290
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_F_000             396
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1923
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.220
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0492
_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)+(0.0286P)²+1.1593P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1144
_reflns_number_gt                1500
_reflns_number_total             1923
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            ic300130y_si_002.cif
_cod_data_source_block           twin4n
_cod_database_code               4329189
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
C1 C 0.19855(15) 0.1038(5) 0.3969(3) 0.0188(6) Uani 1 1 d .
C2 C 0.26542(15) 0.2055(5) 0.3761(3) 0.0183(6) Uani 1 1 d .
H2 H 0.2780 0.3478 0.4202 0.022 Uiso 1 1 calc R
C3 C 0.31589(15) 0.0993(5) 0.2889(3) 0.0174(6) Uani 1 1 d .
C4 C 0.38492(16) 0.2002(5) 0.2657(3) 0.0234(6) Uani 1 1 d .
H4 H 0.3992 0.3403 0.3112 0.028 Uiso 1 1 calc R
C5 C 0.43103(17) 0.0960(6) 0.1780(3) 0.0300(7) Uani 1 1 d .
H5 H 0.4759 0.1666 0.1630 0.036 Uiso 1 1 calc R
C6 C 0.41102(16) -0.1179(5) 0.1101(3) 0.0283(7) Uani 1 1 d .
H6 H 0.4427 -0.1881 0.0502 0.034 Uiso 1 1 calc R
C7 C 0.34541(16) -0.2222(5) 0.1318(3) 0.0238(7) Uani 1 1 d .
H7 H 0.3328 -0.3636 0.0865 0.029 Uiso 1 1 calc R
C8 C 0.29610(15) -0.1193(5) 0.2222(3) 0.0188(6) Uani 1 1 d .
C9 C 0.22758(16) -0.2231(5) 0.2478(3) 0.0209(6) Uani 1 1 d .
H9 H 0.2141 -0.3658 0.2051 0.025 Uiso 1 1 calc R
C10 C 0.18105(15) -0.1173(5) 0.3340(3) 0.0206(6) Uani 1 1 d .
H10 H 0.1371 -0.1912 0.3519 0.025 Uiso 1 1 calc R
C11 C 0.14271(15) 0.2227(5) 0.4794(3) 0.0233(6) Uani 1 1 d .
H11A H 0.1658 0.3541 0.5338 0.028 Uiso 1 1 calc R
H11B H 0.1245 0.1171 0.5496 0.028 Uiso 1 1 calc R
S12 S 0.06507(4) 0.31892(13) 0.34296(7) 0.0206(2) Uani 1 1 d .
C13 C -0.00675(15) 0.3859(5) 0.4591(3) 0.0192(6) Uani 1 1 d .
H13A H -0.0551 0.3917 0.3976 0.023 Uiso 1 1 calc R
H13B H -0.0086 0.2629 0.5311 0.023 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'
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
C2 C1 C10 118.8(3) .
C2 C1 C11 121.9(3) .
C10 C1 C11 119.2(3) .
C1 C2 C3 121.7(3) .
C1 C2 H2 119.1 .
C3 C2 H2 119.1 .
C4 C3 C2 122.8(3) .
C4 C3 C8 118.6(3) .
C2 C3 C8 118.6(2) .
C5 C4 C3 121.2(3) .
C5 C4 H4 119.4 .
C3 C4 H4 119.4 .
C4 C5 C6 120.3(3) .
C4 C5 H5 119.8 .
C6 C5 H5 119.8 .
C7 C6 C5 120.2(3) .
C7 C6 H6 119.9 .
C5 C6 H6 119.9 .
C6 C7 C8 121.1(3) .
C6 C7 H7 119.4 .
C8 C7 H7 119.4 .
C7 C8 C9 122.7(3) .
C7 C8 C3 118.6(3) .
C9 C8 C3 118.7(2) .
C10 C9 C8 121.0(3) .
C10 C9 H9 119.5 .
C8 C9 H9 119.5 .
C9 C10 C1 121.0(3) .
C9 C10 H10 119.5 .
C1 C10 H10 119.5 .
C1 C11 S12 107.68(18) .
C1 C11 H11A 110.2 .
S12 C11 H11A 110.2 .
C1 C11 H11B 110.2 .
S12 C11 H11B 110.2 .
H11A C11 H11B 108.5 .
C13 S12 C11 102.10(13) .
C13 C13 S12 113.0(2) 3_566
C13 C13 H13A 109.0 3_566
S12 C13 H13A 109.0 .
C13 C13 H13B 109.0 3_566
S12 C13 H13B 109.0 .
H13A C13 H13B 107.8 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.372(4) .
C1 C10 1.419(4) .
C1 C11 1.495(4) .
C2 C3 1.419(4) .
C2 H2 0.9300 .
C3 C4 1.411(4) .
C3 C8 1.426(4) .
C4 C5 1.362(4) .
C4 H4 0.9300 .
C5 C6 1.408(4) .
C5 H5 0.9300 .
C6 C7 1.361(4) .
C6 H6 0.9300 .
C7 C8 1.415(4) .
C7 H7 0.9300 .
C8 C9 1.416(4) .
C9 C10 1.362(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 S12 1.826(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
S12 C13 1.811(3) .
C13 C13 1.518(5) 3_566
C13 H13A 0.9700 .
C13 H13B 0.9700 .
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_4
C10 C1 C2 C3 2.4(4) .
C11 C1 C2 C3 -175.5(2) .
C1 C2 C3 C4 180.0(2) .
C1 C2 C3 C8 -0.2(4) .
C2 C3 C4 C5 -178.2(3) .
C8 C3 C4 C5 2.0(4) .
C3 C4 C5 C6 -1.0(4) .
C4 C5 C6 C7 -0.1(4) .
C5 C6 C7 C8 0.1(4) .
C6 C7 C8 C9 -179.7(3) .
C6 C7 C8 C3 0.9(4) .
C4 C3 C8 C7 -1.9(4) .
C2 C3 C8 C7 178.2(2) .
C4 C3 C8 C9 178.7(2) .
C2 C3 C8 C9 -1.1(4) .
C7 C8 C9 C10 -179.1(3) .
C3 C8 C9 C10 0.2(4) .
C8 C9 C10 C1 2.1(4) .
C2 C1 C10 C9 -3.4(4) .
C11 C1 C10 C9 174.6(2) .
C2 C1 C11 S12 105.8(3) .
C10 C1 C11 S12 -72.1(3) .
C1 C11 S12 C13 165.4(2) .
C11 S12 C13 C13 76.7(3) 3_566
