#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:58:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178453 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/74/4027466.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_4027466
loop_
_publ_author_name
'Shin-ichiro Kato'
'Takayuki Furuya'
'Atsushi Kobayashi'
'Masashi Nitani'
'Yutaka Ie'
'Yoshio Aso'
'Toshitada Yoshihara'
'Seiji Tobita'
'Yosuke Nakamura'
_publ_section_title
;
 π-Extended Thiadiazoles Fused with Thienopyrrole or Indole Moieties:
 Synthesis, Structures, and Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7595
_journal_page_last               7606
_journal_paper_doi               10.1021/jo301458m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C18 H14 N4 S3'
_chemical_formula_weight         382.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.0000(16)
_cell_angle_beta                 122.982(2)
_cell_angle_gamma                90.0000(16)
_cell_formula_units_Z            4
_cell_length_a                   13.891(3)
_cell_length_b                   11.994(3)
_cell_length_c                   12.028(3)
_cell_measurement_temperature    150(2)
_cell_volume                     1681.0(7)
_computing_cell_refinement       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_collection       'CrystalClear (Rigaku Corp., 2000)'
_computing_data_reduction        'CrystalClear (Rigaku Corp., 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_method       dtprofit.ref
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0443
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3684
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         5.41
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_T_max  0.8232
_exptl_absorpt_correction_T_min  0.8064
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0386
_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)+(0.0479P)²+0.8475P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1017
_reflns_number_gt                1359
_reflns_number_total             1415
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301458m_si_002.cif
_cod_data_source_block           crystalclear
_cod_original_cell_volume        1680.9(7)
_cod_database_code               4027466
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.5000 -0.31254(6) -0.2500 0.0299(2) Uani 1 2 d S
N1 N 0.57241(12) -0.22557(14) -0.12707(15) 0.0265(4) Uani 1 1 d .
C1 C 0.54117(14) -0.12342(15) -0.17965(17) 0.0210(4) Uani 1 1 d .
C2 C 0.57701(13) -0.01985(16) -0.10988(17) 0.0205(4) Uani 1 1 d .
C3 C 0.53460(13) 0.08124(16) -0.17892(17) 0.0191(4) Uani 1 1 d .
N2 N 0.57065(11) 0.16958(13) -0.08911(13) 0.0196(4) Uani 1 1 d .
C4 C 0.63682(14) 0.12258(16) 0.03723(17) 0.0205(4) Uani 1 1 d .
C5 C 0.69223(14) 0.16232(18) 0.16920(17) 0.0257(4) Uani 1 1 d .
H1 H 0.6943 0.2381 0.1933 0.031 Uiso 1 1 calc R
C6 C 0.74197(15) 0.07653(18) 0.25638(19) 0.0272(5) Uani 1 1 d .
H2 H 0.7837 0.0861 0.3498 0.033 Uiso 1 1 calc R
S2 S 0.72183(4) -0.05212(4) 0.18062(4) 0.0268(2) Uani 1 1 d .
C7 C 0.64371(14) 0.00868(16) 0.02702(17) 0.0211(4) Uani 1 1 d .
C8 C 0.50822(14) 0.27435(15) -0.11012(17) 0.0224(4) Uani 1 1 d .
H3 H 0.4712 0.2717 -0.0594 0.027 Uiso 1 1 calc R
H4 H 0.4468 0.2808 -0.2052 0.027 Uiso 1 1 calc R
C9 C 0.58393(17) 0.37711(17) -0.0687(2) 0.0315(5) Uani 1 1 d .
H5 H 0.6466 0.3703 0.0246 0.047 Uiso 1 1 calc R
H6 H 0.5382 0.4435 -0.0803 0.047 Uiso 1 1 calc R
H7 H 0.6159 0.3839 -0.1237 0.047 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'
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 S1 N1 100.60(12) 2_654 .
C1 N1 S1 105.99(12) . .
N1 C1 C2 126.80(16) . .
N1 C1 C1 113.71(10) . 2_654
C2 C1 C1 119.43(10) . 2_654
C3 C2 C7 106.00(16) . .
C3 C2 C1 120.22(16) . .
C7 C2 C1 133.47(16) . .
N2 C3 C2 109.82(15) . .
N2 C3 C3 130.33(10) . 2_654
C2 C3 C3 119.85(10) . 2_654
C4 N2 C3 106.36(14) . .
C4 N2 C8 120.65(14) . .
C3 N2 C8 125.91(14) . .
C7 C4 N2 109.83(15) . .
C7 C4 C5 114.27(16) . .
N2 C4 C5 135.82(17) . .
C6 C5 C4 110.34(18) . .
C6 C5 H1 124.8 . .
C4 C5 H1 124.8 . .
C5 C6 S2 113.52(15) . .
C5 C6 H2 123.2 . .
S2 C6 H2 123.2 . .
C7 S2 C6 90.81(9) . .
C4 C7 C2 107.95(16) . .
C4 C7 S2 111.04(14) . .
C2 C7 S2 140.88(15) . .
N2 C8 C9 113.56(14) . .
N2 C8 H3 108.9 . .
C9 C8 H3 108.9 . .
N2 C8 H4 108.9 . .
C9 C8 H4 108.9 . .
H3 C8 H4 107.7 . .
C8 C9 H5 109.5 . .
C8 C9 H6 109.5 . .
H5 C9 H6 109.5 . .
C8 C9 H7 109.5 . .
H5 C9 H7 109.5 . .
H6 C9 H7 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 N1 1.6329(16) 2_654
S1 N1 1.6330(16) .
N1 C1 1.338(2) .
C1 C2 1.428(3) .
C1 C1 1.437(4) 2_654
C2 C3 1.405(3) .
C2 C7 1.423(2) .
C3 N2 1.397(2) .
C3 C3 1.435(3) 2_654
N2 C4 1.397(2) .
N2 C8 1.468(2) .
C4 C7 1.380(3) .
C4 C5 1.417(3) .
C5 C6 1.359(3) .
C5 H1 0.9500 .
C6 S2 1.735(2) .
C6 H2 0.9500 .
S2 C7 1.7146(18) .
C8 C9 1.517(3) .
C8 H3 0.9900 .
C8 H4 0.9900 .
C9 H5 0.9800 .
C9 H6 0.9800 .
C9 H7 0.9800 .
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_4
N1 S1 N1 C1 0.16(8) 2_654 .
S1 N1 C1 C2 176.46(13) . .
S1 N1 C1 C1 -0.4(2) . 2_654
N1 C1 C2 C3 -178.59(16) . .
C1 C1 C2 C3 -1.9(3) 2_654 .
N1 C1 C2 C7 -5.9(3) . .
C1 C1 C2 C7 170.81(18) 2_654 .
C7 C2 C3 N2 -1.46(17) . .
C1 C2 C3 N2 173.01(14) . .
C7 C2 C3 C3 178.53(18) . 2_654
C1 C2 C3 C3 -7.0(3) . 2_654
C2 C3 N2 C4 0.33(17) . .
C3 C3 N2 C4 -179.7(2) 2_654 .
C2 C3 N2 C8 -149.96(16) . .
C3 C3 N2 C8 30.1(3) 2_654 .
C3 N2 C4 C7 0.98(17) . .
C8 N2 C4 C7 153.17(15) . .
C3 N2 C4 C5 -175.44(19) . .
C8 N2 C4 C5 -23.2(3) . .
C7 C4 C5 C6 1.1(2) . .
N2 C4 C5 C6 177.44(18) . .
C4 C5 C6 S2 -0.36(19) . .
C5 C6 S2 C7 -0.35(15) . .
N2 C4 C7 C2 -1.90(19) . .
C5 C4 C7 C2 175.36(13) . .
N2 C4 C7 S2 -178.67(10) . .
C5 C4 C7 S2 -1.40(19) . .
C3 C2 C7 C4 2.04(18) . .
C1 C2 C7 C4 -171.37(17) . .
C3 C2 C7 S2 177.25(16) . .
C1 C2 C7 S2 3.8(3) . .
C6 S2 C7 C4 0.98(14) . .
C6 S2 C7 C2 -174.14(19) . .
C4 N2 C8 C9 78.2(2) . .
C3 N2 C8 C9 -135.34(17) . .
