#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/24/7222455.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_7222455
loop_
_publ_author_name
'Alizadeh, Abdolali'
'Vahabi, Amir Hossein'
'Bazgir, Ayoob'
'Khavasi, Hamid Reza'
'Zhu, Zhe'
'Ng, Seik Weng'
_publ_section_title
;
 Highly mild approach towards synthesis of tetrasubstituted thiophenes by
 an organic salt afforded by cyclic thioureas and ketene dithioacetals
;
_journal_issue                   103
_journal_name_full               'RSC Adv.'
_journal_page_first              85028
_journal_paper_doi               10.1039/C5RA15544D
_journal_volume                  5
_journal_year                    2015
_chemical_formula_sum            'C13 H9 N3 O3 S2'
_chemical_formula_weight         319.35
_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
_audit_update_record
;
2015-09-14 deposited with the CCDC.
2015-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.813(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.882(2)
_cell_length_b                   3.9209(5)
_cell_length_c                   20.007(2)
_cell_measurement_reflns_used    2513
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.10
_cell_measurement_theta_min      3.56
_cell_volume                     1410.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω 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  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0433
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5032
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         3.56
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.390
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_correction_T_min  0.8853
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.854
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2513
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.854
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0406
_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)+(0.1129P)²+0.4012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                2013
_reflns_number_total             2513
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra15544d1.cif
_cod_data_source_block           amv228
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7222455
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
N2 N 1.08597(16) 0.2838(9) 0.40724(12) 0.0685(9) Uani 1 1 d .
H2A H 1.1280 0.3677 0.4071 0.082 Uiso 1 1 calc R
H2B H 1.0787 0.2305 0.4463 0.082 Uiso 1 1 calc R
C13 C 0.79275(17) -0.0364(8) 0.15822(15) 0.0524(8) Uani 1 1 d .
H13A H 0.7934 0.2010 0.1467 0.079 Uiso 1 1 calc R
H13B H 0.7429 -0.1221 0.1403 0.079 Uiso 1 1 calc R
H13C H 0.8246 -0.1609 0.1376 0.079 Uiso 1 1 calc R
N3 N 0.9168(2) -0.0912(11) 0.44477(16) 0.0913(13) Uani 1 1 d .
S1 S 0.95606(3) 0.21961(16) 0.21465(3) 0.0326(2) Uani 1 1 d .
S2 S 0.82502(4) -0.08688(17) 0.25148(4) 0.0395(2) Uani 1 1 d .
C3 C 1.17819(14) 0.3762(7) 0.18384(14) 0.0373(6) Uani 1 1 d .
H3 H 1.2153 0.2709 0.2196 0.045 Uiso 1 1 calc R
O3 O 1.16362(12) 0.4685(7) 0.31855(10) 0.0595(6) Uani 1 1 d .
C10 C 0.96015(15) 0.1031(7) 0.34158(14) 0.0403(6) Uani 1 1 d .
C11 C 0.91391(14) 0.0762(6) 0.27371(13) 0.0330(6) Uani 1 1 d .
C4 C 1.11214(13) 0.4713(6) 0.19595(13) 0.0319(6) Uani 1 1 d .
C5 C 1.05629(14) 0.6214(6) 0.14176(13) 0.0341(6) Uani 1 1 d .
H5 H 1.0113 0.6791 0.1487 0.041 Uiso 1 1 calc R
C1 C 1.13387(15) 0.5910(7) 0.06869(13) 0.0371(6) Uani 1 1 d .
C7 C 1.10645(14) 0.4210(7) 0.26860(13) 0.0381(6) Uani 1 1 d .
C6 C 1.06721(15) 0.6854(7) 0.07772(14) 0.0391(6) Uani 1 1 d .
H6 H 1.0304 0.7897 0.0416 0.047 Uiso 1 1 calc R
N1 N 1.14639(16) 0.6701(8) 0.00110(14) 0.0598(7) Uani 1 1 d .
O1 O 1.2028(2) 0.5676(9) -0.00852(16) 0.1043(11) Uani 1 1 d .
C2 C 1.18983(15) 0.4342(7) 0.12042(14) 0.0400(6) Uani 1 1 d .
H2 H 1.2340 0.3698 0.1126 0.048 Uiso 1 1 calc R
C9 C 1.03200(16) 0.2362(7) 0.34679(14) 0.0414(7) Uani 1 1 d .
C12 C 0.93710(18) -0.0033(9) 0.39961(15) 0.0566(9) Uani 1 1 d .
C8 C 1.03877(14) 0.3152(7) 0.28081(12) 0.0360(6) Uani 1 1 d .
O2 O 1.09935(15) 0.8391(9) -0.04145(12) 0.0880(9) 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'
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
C9 N2 H2A 120.0
C9 N2 H2B 120.0
H2A N2 H2B 120.0
S2 C13 H13A 109.5
S2 C13 H13B 109.5
H13A C13 H13B 109.5
S2 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 S1 C8 92.52(12)
C11 S2 C13 102.86(13)
C2 C3 C4 121.5(2)
C2 C3 H3 119.3
C4 C3 H3 119.3
C11 C10 C12 121.6(3)
C11 C10 C9 113.7(2)
C12 C10 C9 124.7(3)
C10 C11 S1 111.59(19)
C10 C11 S2 123.9(2)
S1 C11 S2 124.52(16)
C5 C4 C3 118.9(2)
C5 C4 C7 123.2(2)
C3 C4 C7 117.8(2)
C6 C5 C4 120.5(2)
C6 C5 H5 119.8
C4 C5 H5 119.8
C6 C1 C2 122.9(2)
C6 C1 N1 118.3(2)
C2 C1 N1 118.8(2)
O3 C7 C8 120.5(2)
O3 C7 C4 117.2(2)
C8 C7 C4 122.3(2)
C1 C6 C5 118.4(2)
C1 C6 H6 120.8
C5 C6 H6 120.8
O1 N1 O2 124.0(3)
O1 N1 C1 118.2(3)
O2 N1 C1 117.8(3)
C3 C2 C1 117.8(2)
C3 C2 H2 121.1
C1 C2 H2 121.1
N2 C9 C8 124.0(2)
N2 C9 C10 124.2(2)
C8 C9 C10 111.8(2)
N3 C12 C10 178.1(3)
C9 C8 C7 124.6(2)
C9 C8 S1 110.37(19)
C7 C8 S1 124.63(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C9 1.335(4)
N2 H2A 0.8600
N2 H2B 0.8600
C13 S2 1.788(3)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
N3 C12 1.138(4)
S1 C11 1.709(2)
S1 C8 1.751(3)
S2 C11 1.723(3)
C3 C2 1.371(4)
C3 C4 1.392(4)
C3 H3 0.9300
O3 C7 1.240(3)
C10 C11 1.375(4)
C10 C12 1.422(4)
C10 C9 1.427(4)
C4 C5 1.391(4)
C4 C7 1.503(3)
C5 C6 1.382(3)
C5 H5 0.9300
C1 C6 1.376(4)
C1 C2 1.377(4)
C1 N1 1.475(3)
C7 C8 1.434(4)
C6 H6 0.9300
N1 O1 1.207(4)
N1 O2 1.221(4)
C2 H2 0.9300
C9 C8 1.399(3)
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
C12 C10 C11 S1 -179.5(2)
C9 C10 C11 S1 -1.2(3)
C12 C10 C11 S2 -0.3(4)
C9 C10 C11 S2 178.13(19)
C8 S1 C11 C10 0.8(2)
C8 S1 C11 S2 -178.48(17)
C13 S2 C11 C10 177.4(2)
C13 S2 C11 S1 -3.4(2)
C2 C3 C4 C5 1.5(4)
C2 C3 C4 C7 -175.6(2)
C3 C4 C5 C6 -2.2(4)
C7 C4 C5 C6 174.8(2)
C5 C4 C7 O3 -141.1(3)
C3 C4 C7 O3 35.8(4)
C5 C4 C7 C8 40.2(4)
C3 C4 C7 C8 -142.8(3)
C2 C1 C6 C5 0.4(4)
N1 C1 C6 C5 -178.0(2)
C4 C5 C6 C1 1.3(4)
C6 C1 N1 O1 -175.2(3)
C2 C1 N1 O1 6.3(4)
C6 C1 N1 O2 5.6(4)
C2 C1 N1 O2 -172.8(3)
C4 C3 C2 C1 0.1(4)
C6 C1 C2 C3 -1.1(4)
N1 C1 C2 C3 177.3(3)
C11 C10 C9 N2 -179.8(3)
C12 C10 C9 N2 -1.5(5)
C11 C10 C9 C8 1.0(4)
C12 C10 C9 C8 179.3(3)
C11 C10 C12 N3 1(13)
C9 C10 C12 N3 -177(100)
N2 C9 C8 C7 7.3(5)
C10 C9 C8 C7 -173.5(3)
N2 C9 C8 S1 -179.6(3)
C10 C9 C8 S1 -0.3(3)
O3 C7 C8 C9 -4.4(5)
C4 C7 C8 C9 174.2(2)
O3 C7 C8 S1 -176.6(2)
C4 C7 C8 S1 2.0(4)
C11 S1 C8 C9 -0.3(2)
C11 S1 C8 C7 172.9(3)
