#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023480.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_4023480
loop_
_publ_author_name
'Yu-Chang Chang'
'Yu-Da Chen'
'Chih-Hsin Chen'
'Yuh-Sheng Wen'
'Jiann T. Lin'
'Hsing-Yin Chen'
'Ming-Yu Kuo'
'Ito Chao'
_publ_section_title
;
 Crystal Engineering for π-π Stacking via Interaction between
 Electron-Rich and Electron-Deficient Heteroaromatics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4608
_journal_page_last               4614
_journal_paper_doi               10.1021/jo800546j
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C13 H7 N S3'
_chemical_formula_sum            'C13 H7 N S3'
_chemical_formula_weight         273.38
_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                 104.255(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6857(5)
_cell_length_b                   6.0341(2)
_cell_length_c                   14.1529(5)
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      31.39
_cell_measurement_theta_min      2.38
_cell_volume                     1132.77(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.0(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0440
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8690
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  0.9996
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.945
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0307
_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)+(0.0427P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                1464
_reflns_number_total             2001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800546j-File004.cif
_cod_data_source_block           i7254
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4023480
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.06628(4) -0.16127(10) 0.33024(4) 0.02577(18) Uani 1 1 d . . .
S2 S 0.21417(4) 0.18084(10) 0.31873(4) 0.02212(17) Uani 1 1 d . . .
S3 S 0.17249(4) 0.64078(11) 0.52411(4) 0.03063(19) Uani 1 1 d . . .
N7 N 0.07349(12) -0.1916(3) 0.23445(12) 0.0218(4) Uani 1 1 d . . .
C1 C -0.07586(15) -0.3749(4) 0.24636(15) 0.0232(5) Uani 1 1 d . . .
C2 C -0.14965(16) -0.5392(4) 0.22042(16) 0.0282(6) Uani 1 1 d . . .
H2 H -0.2043 -0.5449 0.2484 0.034 Uiso 1 1 calc R . .
C3 C -0.13818(16) -0.6922(4) 0.15177(16) 0.0294(6) Uani 1 1 d . . .
H3 H -0.1858 -0.8040 0.1332 0.035 Uiso 1 1 calc R . .
C4 C -0.05653(16) -0.6824(4) 0.10970(16) 0.0267(6) Uani 1 1 d . . .
H4 H -0.0507 -0.7889 0.0639 0.032 Uiso 1 1 calc R . .
C5 C 0.01489(16) -0.5222(4) 0.13352(16) 0.0271(6) Uani 1 1 d . . .
H5 H 0.0689 -0.5178 0.1045 0.033 Uiso 1 1 calc R . .
C6 C 0.00540(15) -0.3650(4) 0.20231(15) 0.0227(5) Uani 1 1 d . . .
C8 C 0.04526(15) -0.0755(4) 0.30036(15) 0.0206(5) Uani 1 1 d . . .
C9 C 0.10120(15) 0.1141(4) 0.34789(15) 0.0207(5) Uani 1 1 d . . .
C10 C 0.07785(16) 0.2533(4) 0.41536(15) 0.0235(5) Uani 1 1 d . . .
H10 H 0.0204 0.2415 0.4390 0.028 Uiso 1 1 calc R . .
C11 C 0.15279(15) 0.4176(4) 0.44429(15) 0.0216(5) Uani 1 1 d . . .
C12 C 0.23121(15) 0.4014(4) 0.39890(14) 0.0210(5) Uani 1 1 d . . .
C13 C 0.30700(15) 0.5656(4) 0.42770(15) 0.0219(5) Uani 1 1 d . . .
H13 H 0.3643 0.5766 0.4038 0.026 Uiso 1 1 calc R . .
C14 C 0.28472(16) 0.7038(4) 0.49459(15) 0.0248(5) Uani 1 1 d . . .
H14 H 0.3258 0.8216 0.5221 0.030 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
S S 0.1246 0.1234 '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'
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'
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
_geom_angle_publ_flag
C1 S1 C8 88.73(10) . . ?
C12 S2 C9 90.38(10) . . ?
C14 S3 C11 91.05(10) . . ?
C8 N7 C6 110.14(18) . . ?
C2 C1 C6 120.9(2) . . ?
C2 C1 S1 129.38(18) . . ?
C6 C1 S1 109.73(16) . . ?
C3 C2 C1 117.4(2) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 118.4(2) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 N7 124.66(19) . . ?
C5 C6 C1 120.2(2) . . ?
N7 C6 C1 115.09(19) . . ?
N7 C8 C9 122.90(19) . . ?
N7 C8 S1 116.31(17) . . ?
C9 C8 S1 120.78(17) . . ?
C10 C9 C8 128.5(2) . . ?
C10 C9 S2 113.39(17) . . ?
C8 C9 S2 118.11(16) . . ?
C9 C10 C11 110.83(19) . . ?
C9 C10 H10 124.6 . . ?
C11 C10 H10 124.6 . . ?
C12 C11 C10 114.00(19) . . ?
C12 C11 S3 110.07(16) . . ?
C10 C11 S3 135.93(17) . . ?
C11 C12 C13 114.38(19) . . ?
C11 C12 S2 111.40(16) . . ?
C13 C12 S2 134.22(17) . . ?
C14 C13 C12 110.9(2) . . ?
C14 C13 H13 124.5 . . ?
C12 C13 H13 124.5 . . ?
C13 C14 S3 113.59(18) . . ?
C13 C14 H14 123.2 . . ?
S3 C14 H14 123.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.735(2) . ?
S1 C8 1.759(2) . ?
S2 C12 1.727(2) . ?
S2 C9 1.743(2) . ?
S3 C14 1.730(2) . ?
S3 C11 1.736(2) . ?
N7 C8 1.299(3) . ?
N7 C6 1.400(3) . ?
C1 C2 1.398(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.377(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.357(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C8 C9 1.447(3) . ?
C9 C10 1.367(3) . ?
C10 C11 1.412(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C12 C13 1.420(3) . ?
C13 C14 1.352(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658684
