#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:00:38 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179648 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/01/4510188.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_4510188
loop_
_publ_author_name
'Pham, Phuong-Truc T.'
'Bader, Mamoun M.'
_publ_section_title
;
 Inter- and Intramolecular Interactions in Some Bromo- and
 Tricyanovinyl-Substituted Thiophenes and Ethylenedioxythiophenes
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              916
_journal_paper_doi               10.1021/cg401513n
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C13 H5 N3 S2'
_chemical_formula_weight         267.32
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8613(10)
_cell_length_b                   24.495(3)
_cell_length_c                   6.1207(8)
_cell_measurement_temperature    173(2)
_cell_volume                     1178.6(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7326
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    0.433
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.8493
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2372
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0355P)²+0.3066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0691
_reflns_number_gt                2214
_reflns_number_total             2372
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg401513n_si_008.cif
_cod_data_source_block           2ttcv
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'multiscan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_symmetry_cell_setting' tag value 'Orthorombic' was replaced with
'orthorhombic' value as specified in the replacement file
'/home/robertas/cod-tools/perl-scripts/inputs/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               4510188
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
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
S2 S 0.59766(6) 0.730917(18) 0.97676(11) 0.02460(12) Uani 1 1 d
S1 S 0.53667(7) 0.85805(2) 0.82591(10) 0.02874(13) Uani 1 1 d
C13 C 0.5107(3) 0.62009(8) 0.7955(4) 0.0249(5) Uani 1 1 d
C12 C 0.6046(3) 0.53655(8) 0.9763(5) 0.0277(4) Uani 1 1 d
N2 N 0.6131(3) 0.49001(7) 0.9707(5) 0.0400(5) Uani 1 1 d
C10 C 0.5939(3) 0.59516(7) 0.9777(5) 0.0246(4) Uani 1 1 d
N3 N 0.4469(3) 0.64021(7) 0.6479(4) 0.0326(4) Uani 1 1 d
N1 N 0.8088(3) 0.57169(7) 1.4570(4) 0.0378(5) Uani 1 1 d
C7 C 0.7325(3) 0.71026(9) 1.3505(4) 0.0275(5) Uani 1 1 d
C6 C 0.7250(3) 0.76692(8) 1.3357(4) 0.0270(4) Uani 1 1 d
C8 C 0.6669(3) 0.68370(8) 1.1691(4) 0.0236(4) Uani 1 1 d
C1 C 0.5739(3) 0.92615(9) 0.8680(5) 0.0306(5) Uani 1 1 d
C5 C 0.6553(3) 0.78514(8) 1.1414(4) 0.0221(4) Uani 1 1 d
C3 C 0.6927(3) 0.88728(8) 1.1785(4) 0.0270(5) Uani 1 1 d
C9 C 0.6626(3) 0.62542(8) 1.1442(4) 0.0239(4) Uani 1 1 d
C11 C 0.7436(3) 0.59457(8) 1.3187(4) 0.0262(4) Uani 1 1 d
C4 C 0.6347(3) 0.84092(8) 1.0699(4) 0.0229(4) Uani 1 1 d
C2 C 0.6563(3) 0.93543(9) 1.0588(4) 0.0292(5) Uani 1 1 d
H3 H 0.741(3) 0.8860(8) 1.293(4) 0.018(6) Uiso 1 1 d
H7 H 0.774(3) 0.6902(10) 1.477(5) 0.034(6) Uiso 1 1 d
H1 H 0.540(3) 0.9518(10) 0.763(5) 0.033(7) Uiso 1 1 d
H2 H 0.689(3) 0.9677(11) 1.105(5) 0.030(7) Uiso 1 1 d
H6 H 0.756(3) 0.7900(10) 1.429(5) 0.034(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S2 0.0299(3) 0.0202(2) 0.0236(2) -0.0013(2) -0.0032(2) -0.00066(18)
S1 0.0300(3) 0.0266(2) 0.0296(3) 0.0016(3) -0.0057(3) -0.0022(2)
C13 0.0275(11) 0.0199(8) 0.0275(13) -0.0036(9) 0.0019(10) -0.0026(7)
C12 0.0304(10) 0.0285(10) 0.0242(10) -0.0012(12) 0.0021(11) -0.0006(8)
N2 0.0561(13) 0.0257(9) 0.0381(11) -0.0017(11) 0.0029(12) 0.0020(8)
C10 0.0262(9) 0.0234(8) 0.0243(10) 0.0007(11) 0.0015(10) -0.0007(7)
N3 0.0385(11) 0.0290(9) 0.0303(11) 0.0006(9) -0.0049(9) -0.0011(8)
N1 0.0449(11) 0.0300(9) 0.0384(13) 0.0041(10) -0.0097(11) 0.0016(8)
C7 0.0321(11) 0.0272(10) 0.0231(13) 0.0021(10) -0.0013(10) -0.0006(8)
C6 0.0331(11) 0.0243(10) 0.0237(11) -0.0042(11) -0.0035(10) -0.0031(8)
C8 0.0253(10) 0.0209(9) 0.0246(11) 0.0045(8) 0.0022(9) -0.0003(8)
C1 0.0294(11) 0.0233(10) 0.0391(15) 0.0062(10) -0.0023(10) -0.0005(8)
C5 0.0221(10) 0.0209(9) 0.0232(11) -0.0038(8) 0.0015(9) -0.0016(7)
C3 0.0269(11) 0.0239(10) 0.0302(13) 0.0001(10) -0.0002(11) -0.0001(8)
C9 0.0234(10) 0.0244(9) 0.0239(11) 0.0027(9) 0.0027(9) 0.0008(8)
C11 0.0282(10) 0.0238(9) 0.0267(11) -0.0029(10) -0.0011(11) -0.0004(7)
C4 0.0214(10) 0.0234(10) 0.0239(11) 0.0005(8) 0.0014(9) 0.0006(8)
C2 0.0322(12) 0.0196(10) 0.0358(13) -0.0004(9) -0.0008(10) -0.0020(9)
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
C5 S2 C8 91.97(11)
C1 S1 C4 91.74(12)
N3 C13 C10 178.8(3)
N2 C12 C10 178.6(3)
C9 C10 C13 121.95(17)
C9 C10 C12 121.4(2)
C13 C10 C12 116.6(2)
C8 C7 C6 113.6(2)
C5 C6 C7 113.2(2)
C7 C8 C9 124.1(2)
C7 C8 S2 110.28(15)
C9 C8 S2 125.63(18)
C2 C1 S1 112.00(19)
C6 C5 C4 127.60(19)
C6 C5 S2 110.94(15)
C4 C5 S2 121.43(17)
C4 C3 C2 111.5(2)
C10 C9 C8 128.7(2)
C10 C9 C11 115.92(19)
C8 C9 C11 115.4(2)
N1 C11 C9 178.2(2)
C3 C4 C5 126.2(2)
C3 C4 S1 111.07(17)
C5 C4 S1 122.70(16)
C1 C2 C3 113.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S2 C5 1.728(2)
S2 C8 1.738(2)
S1 C1 1.713(2)
S1 C4 1.732(2)
C13 N3 1.144(3)
C13 C10 1.430(4)
C12 N2 1.142(3)
C12 C10 1.438(3)
C10 C9 1.371(3)
N1 C11 1.137(3)
C7 C8 1.386(3)
C7 C6 1.392(3)
C6 C5 1.383(3)
C8 C9 1.436(3)
C1 C2 1.355(3)
C5 C4 1.444(3)
C3 C4 1.392(3)
C3 C2 1.417(3)
C9 C11 1.455(3)
