#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:52:34 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180320 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/34/7153499.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_7153499
loop_
_publ_author_name
'Cantillo, David'
'Avalos, Martín'
'Babiano, Reyes'
'Cintas, Pedro'
'Jiménez, José L'
'Light, Mark E.'
'Palacios, Juan C.'
'Rodríguez, Valentín'
_publ_section_title
;
 Push-pull 1,3-thiazolium-5-thiolates. Formation via concerted and
 stepwise pathways, and theoretical evaluation of NLO properties.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5367
_journal_page_last               5374
_journal_paper_doi               10.1039/c0ob00416b
_journal_volume                  8
_journal_year                    2010
_chemical_formula_sum            'C17 H14 N2 O3 S2'
_chemical_formula_weight         358.42
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 118.6420(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.1380(3)
_cell_length_b                   13.8360(2)
_cell_length_c                   11.5630(3)
_cell_measurement_reflns_used    10753
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1563.87(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular
structures program for Mac and Windows. CrystalMaker Software Ltd,
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20458
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  0.9650
_exptl_absorpt_correction_T_min  0.9316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Dark Red'
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3565
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0412P)²+0.9538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0960
_reflns_number_gt                3017
_reflns_number_total             3565
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c0ob00416b.txt
_cod_data_source_block           Compound16
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7153499
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
S1 S 0.43386(4) 0.38961(3) 0.39606(4) 0.01752(12) Uani 1 1 d .
S2 S 0.15456(5) 0.47339(3) 0.28722(4) 0.02004(12) Uani 1 1 d .
O1 O 1.04249(16) 0.08832(12) 0.55676(16) 0.0438(4) Uani 1 1 d .
O2 O 1.09598(14) 0.15771(12) 0.74304(15) 0.0375(4) Uani 1 1 d .
O3 O -0.29176(13) 0.13169(9) 0.20072(13) 0.0247(3) Uani 1 1 d .
N1 N 1.01416(16) 0.13624(11) 0.62888(16) 0.0235(3) Uani 1 1 d .
N2 N 0.35881(14) 0.22566(10) 0.42857(14) 0.0155(3) Uani 1 1 d .
C1 C 0.87292(18) 0.16991(13) 0.57862(17) 0.0198(4) Uani 1 1 d .
C2 C 0.76598(19) 0.10848(12) 0.50220(18) 0.0208(4) Uani 1 1 d .
H2 H 0.7830 0.0464 0.4781 0.025 Uiso 1 1 calc R
C3 C 0.63364(18) 0.13967(12) 0.46160(17) 0.0196(4) Uani 1 1 d .
H3 H 0.5588 0.0979 0.4112 0.023 Uiso 1 1 calc R
C4 C 0.60950(17) 0.23281(12) 0.49458(16) 0.0165(3) Uani 1 1 d .
C5 C 0.72109(18) 0.29392(12) 0.56788(17) 0.0185(4) Uani 1 1 d .
H5 H 0.7053 0.3580 0.5870 0.022 Uiso 1 1 calc R
C6 C 0.85341(18) 0.26228(13) 0.61259(17) 0.0201(4) Uani 1 1 d .
H6 H 0.9291 0.3027 0.6653 0.024 Uiso 1 1 calc R
C7 C 0.47153(17) 0.27219(12) 0.44489(16) 0.0165(3) Uani 1 1 d .
C8 C 0.23836(17) 0.28042(12) 0.37050(16) 0.0157(3) Uani 1 1 d .
C9 C 0.26157(18) 0.37596(12) 0.34937(16) 0.0168(3) Uani 1 1 d .
C10 C 0.36484(19) 0.12991(12) 0.48823(18) 0.0206(4) Uani 1 1 d .
H10A H 0.3464 0.0792 0.4226 0.031 Uiso 1 1 calc R
H10B H 0.2961 0.1269 0.5180 0.031 Uiso 1 1 calc R
H10C H 0.4560 0.1202 0.5636 0.031 Uiso 1 1 calc R
C11 C 0.10398(17) 0.23625(12) 0.33081(16) 0.0164(3) Uani 1 1 d .
C12 C 0.06537(18) 0.14777(12) 0.26429(17) 0.0185(4) Uani 1 1 d .
H12 H 0.1299 0.1126 0.2494 0.022 Uiso 1 1 calc R
C13 C -0.06550(18) 0.11003(12) 0.21933(17) 0.0184(4) Uani 1 1 d .
H13 H -0.0896 0.0498 0.1745 0.022 Uiso 1 1 calc R
C14 C -0.16070(17) 0.16122(13) 0.24061(17) 0.0183(4) Uani 1 1 d .
C15 C -0.12328(18) 0.24927(13) 0.30768(18) 0.0216(4) Uani 1 1 d .
H15 H -0.1879 0.2842 0.3227 0.026 Uiso 1 1 calc R
C16 C 0.00645(18) 0.28599(12) 0.35221(17) 0.0193(4) Uani 1 1 d .
H16 H 0.0303 0.3458 0.3981 0.023 Uiso 1 1 calc R
C17 C -0.3276(2) 0.03549(14) 0.1505(2) 0.0272(4) Uani 1 1 d .
H17A H -0.3222 0.0297 0.0686 0.041 Uiso 1 1 calc R
H17B H -0.4211 0.0213 0.1329 0.041 Uiso 1 1 calc R
H17C H -0.2641 -0.0104 0.2156 0.041 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
C7 S1 C9 93.39(8)
C14 O3 C17 117.43(14)
O1 N1 O2 124.38(17)
O1 N1 C1 118.78(16)
O2 N1 C1 116.83(15)
C7 N2 C8 115.13(14)
C7 N2 C10 122.25(14)
C8 N2 C10 121.78(14)
C2 C1 C6 122.97(17)
C2 C1 N1 119.30(16)
C6 C1 N1 117.71(16)
C3 C2 C1 118.43(16)
C2 C3 C4 120.31(16)
C5 C4 C3 119.15(16)
C5 C4 C7 118.18(15)
C3 C4 C7 122.41(15)
C6 C5 C4 120.89(16)
C5 C6 C1 118.15(16)
N2 C7 C4 127.76(15)
N2 C7 S1 110.22(12)
C4 C7 S1 122.01(12)
C9 C8 N2 112.48(15)
C9 C8 C11 125.93(15)
N2 C8 C11 121.48(14)
C8 C9 S2 132.16(14)
C8 C9 S1 108.64(13)
S2 C9 S1 119.20(10)
C12 C11 C16 117.75(16)
C12 C11 C8 122.23(15)
C16 C11 C8 119.90(15)
C13 C12 C11 121.59(16)
C14 C13 C12 119.53(16)
O3 C14 C13 124.73(16)
O3 C14 C15 115.77(15)
C13 C14 C15 119.49(16)
C16 C15 C14 120.65(16)
C15 C16 C11 120.98(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C7 1.7050(17)
S1 C9 1.7368(18)
S2 C9 1.7127(17)
O1 N1 1.219(2)
O2 N1 1.228(2)
O3 C14 1.366(2)
O3 C17 1.430(2)
N1 C1 1.467(2)
N2 C7 1.341(2)
N2 C8 1.400(2)
N2 C10 1.480(2)
C1 C2 1.383(3)
C1 C6 1.384(3)
C2 C3 1.384(3)
C3 C4 1.406(2)
C4 C5 1.403(2)
C4 C7 1.464(2)
C5 C6 1.379(3)
C8 C9 1.391(2)
C8 C11 1.472(2)
C11 C12 1.399(2)
C11 C16 1.404(2)
C12 C13 1.393(2)
C13 C14 1.392(2)
C14 C15 1.396(3)
C15 C16 1.378(2)
