#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:47:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180316 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/30/7153075.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_7153075
loop_
_publ_author_name
'Marco, A Belén'
'Andreu, Raquel'
'Franco, Santiago'
'Garín, Javier'
'Orduna, Jesús'
'Villacampa, Belén'
'Diosdado, Beatriz E.'
'López Navarrete, Juan T'
'Casado, Juan'
_publ_section_title
;
 Push-pull systems bearing a quinoid/aromatic thieno[3,2-b]thiophene
 moiety: synthesis, ground state polarization and second-order nonlinear
 properties.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6338
_journal_page_last               6349
_journal_paper_doi               10.1039/c3ob41278d
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C24 H24 N2 O S2'
_chemical_formula_sum            'C24 H24 N2 O S2'
_chemical_formula_weight         420.57
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-12-16 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.064(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.0980(5)
_cell_length_b                   6.7887(4)
_cell_length_c                   15.8764(10)
_cell_measurement_reflns_used    1122
_cell_measurement_temperature    296(1)
_cell_measurement_theta_max      28.7938
_cell_measurement_theta_min      2.9614
_cell_volume                     1184.32(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_molecular_graphics    'Diamond 3.2g'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    SIR-92
_diffrn_ambient_temperature      296(1)
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7220
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.97
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Multi-scan absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                1556
_reflns_number_total             2275
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c3ob41278d.txt
_cod_data_source_block           8
_cod_original_sg_symbol_H-M      P21/m
_cod_database_code               7153075
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
_atom_site_refinement_flags
O1 O 0.8372(3) 0.2500 0.83040(17) 0.0663(8) Uani 1 2 d S
C1 C 0.8773(4) 0.2500 0.7529(3) 0.0550(10) Uani 1 2 d S
C2 C 0.7968(3) 0.2500 0.6812(2) 0.0483(9) Uani 1 2 d S
H2 H 0.8253 0.2500 0.6289 0.058 Uiso 1 2 calc SR
C3 C 0.6689(3) 0.2500 0.6833(2) 0.0413(8) Uani 1 2 d S
C4 C 0.6340(4) 0.2500 0.7661(2) 0.0503(9) Uani 1 2 d S
H4 H 0.5516 0.2500 0.7713 0.060 Uiso 1 2 calc SR
C5 C 0.7148(4) 0.2500 0.8364(3) 0.0569(10) Uani 1 2 d S
C6 C 1.0141(4) 0.2500 0.7626(3) 0.0768(13) Uani 1 2 d S
C7 C 1.0603(4) 0.4358(7) 0.8113(3) 0.1297(17) Uani 1 1 d .
H7A H 1.1476 0.4385 0.8180 0.195 Uiso 1 1 calc R
H7B H 1.0338 0.4354 0.8663 0.195 Uiso 1 1 calc R
H7C H 1.0286 0.5501 0.7802 0.195 Uiso 1 1 calc R
C8 C 1.0579(4) 0.2500 0.6762(4) 0.1067(19) Uani 1 2 d S
H8A H 1.1453 0.2500 0.6837 0.160 Uiso 1 2 d SR
H8B H 1.0281 0.3655 0.6451 0.160 Uiso 1 1 d R
C9 C 0.6919(5) 0.2500 0.9282(3) 0.0825(15) Uani 1 2 d S
C10 C 0.5572(6) 0.2500 0.9333(3) 0.118(2) Uani 1 2 d S
H10A H 0.5414 0.2500 0.9941 0.176 Uiso 1 2 d SR
H10B H 0.5261 0.3846 0.9140 0.176 Uiso 1 1 d R
C11 C 0.7457(5) 0.4362(9) 0.9700(3) 0.190(3) Uani 1 1 d .
H11A H 0.7066 0.5487 0.9414 0.284 Uiso 1 1 calc R
H11B H 0.8313 0.4405 0.9665 0.284 Uiso 1 1 calc R
H11C H 0.7333 0.4376 1.0286 0.284 Uiso 1 1 calc R
C12 C 0.5804(3) 0.2500 0.6121(2) 0.0418(8) Uani 1 2 d S
H12 H 0.4996 0.2500 0.6215 0.050 Uiso 1 2 calc SR
C13 C 0.6023(3) 0.2500 0.5282(2) 0.0384(8) Uani 1 2 d S
H13 H 0.6832 0.2500 0.5190 0.046 Uiso 1 2 calc SR
C14 C 0.5148(3) 0.2500 0.4570(2) 0.0350(8) Uani 1 2 d S
C15 C 0.5398(3) 0.2500 0.3707(2) 0.0409(9) Uani 1 2 d S
S1 S 0.40717(9) 0.2500 0.29744(6) 0.0534(3) Uani 1 2 d S
C16 C 0.3167(3) 0.2500 0.3779(3) 0.0482(9) Uani 1 2 d S
C17 C 0.1896(4) 0.2500 0.3788(3) 0.0686(13) Uani 1 2 d S
H17 H 0.1315 0.2500 0.3305 0.082 Uiso 1 2 calc SR
C18 C 0.1639(4) 0.2500 0.4589(4) 0.0766(14) Uani 1 2 d S
H18 H 0.0849 0.2500 0.4723 0.092 Uiso 1 2 calc SR
S2 S 0.29054(9) 0.2500 0.53429(7) 0.0614(4) Uani 1 2 d S
C19 C 0.3840(3) 0.2500 0.4566(2) 0.0416(9) Uani 1 2 d S
C20 C 0.6502(4) 0.2500 0.3378(2) 0.0521(10) Uani 1 2 d S
C21 C 0.7668(4) 0.2500 0.3876(3) 0.0601(11) Uani 1 2 d S
N1 N 0.8614(3) 0.2500 0.4261(3) 0.0899(13) Uani 1 2 d S
C22 C 0.6492(5) 0.2500 0.2483(3) 0.0851(15) Uani 1 2 d S
N2 N 0.6434(5) 0.2500 0.1762(3) 0.144(2) Uani 1 2 d S
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 O1 C5 120.8(3) . .
C2 C1 O1 120.0(4) . .
C2 C1 C6 128.9(4) . .
O1 C1 C6 111.1(4) . .
C1 C2 C3 121.7(4) . .
C1 C2 H2 119.1 . .
C3 C2 H2 119.1 . .
C12 C3 C4 120.0(3) . .
C12 C3 C2 125.0(3) . .
C4 C3 C2 115.1(3) . .
C5 C4 C3 122.5(4) . .
C5 C4 H4 118.8 . .
C3 C4 H4 118.8 . .
C4 C5 O1 119.9(4) . .
C4 C5 C9 128.6(4) . .
O1 C5 C9 111.5(4) . .
C1 C6 C8 110.7(4) . .
C1 C6 C7 108.3(3) . .
C8 C6 C7 109.2(3) . .
C1 C6 C7 108.3(3) . 4_565
C8 C6 C7 109.2(3) . 4_565
C7 C6 C7 111.1(5) . 4_565
C6 C7 H7A 109.5 . .
C6 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C6 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C10 C9 C11 108.0(3) . .
C10 C9 C11 108.0(3) . 4_565
C11 C9 C11 113.5(6) . 4_565
C10 C9 C5 110.7(4) . .
C11 C9 C5 108.3(3) . .
C11 C9 C5 108.3(3) 4_565 .
C9 C10 H10A 111.0 . .
C9 C10 H10B 106.5 . .
H10A C10 H10B 101.1 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C13 C12 C3 125.7(3) . .
C13 C12 H12 117.2 . .
C3 C12 H12 117.2 . .
C14 C13 C12 126.0(3) . .
C14 C13 H13 117.0 . .
C12 C13 H13 117.0 . .
C13 C14 C15 124.9(3) . .
C13 C14 C19 126.2(3) . .
C15 C14 C19 108.9(3) . .
C20 C15 C14 130.8(3) . .
C20 C15 S1 117.0(3) . .
C14 C15 S1 112.2(2) . .
C16 S1 C15 91.79(17) . .
C19 C16 C17 114.2(4) . .
C19 C16 S1 112.1(3) . .
C17 C16 S1 133.7(4) . .
C18 C17 C16 110.8(4) . .
C18 C17 H17 124.6 . .
C16 C17 H17 124.6 . .
C17 C18 S2 113.6(3) . .
C17 C18 H18 123.2 . .
S2 C18 H18 123.2 . .
C18 S2 C19 91.0(2) . .
C16 C19 C14 115.0(3) . .
C16 C19 S2 110.4(3) . .
C14 C19 S2 134.5(3) . .
C15 C20 C21 124.8(3) . .
C15 C20 C22 119.4(4) . .
C21 C20 C22 115.8(4) . .
N1 C21 C20 178.6(5) . .
N2 C22 C20 177.2(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.366(5) .
O1 C5 1.375(5) .
C1 C2 1.345(5) .
C1 C6 1.504(6) .
C2 C3 1.425(5) .
C2 H2 0.9300 .
C3 C12 1.390(5) .
C3 C4 1.421(5) .
C4 C5 1.330(5) .
C4 H4 0.9300 .
C5 C9 1.514(6) .
C6 C8 1.519(7) .
C6 C7 1.530(4) .
C6 C7 1.530(4) 4_565
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C9 C10 1.509(7) .
C9 C11 1.511(5) .
C9 C11 1.511(5) 4_565
C10 H10A 1.0060 .
C10 H10B 1.0088 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C13 1.386(5) .
C12 H12 0.9300 .
C13 C14 1.383(4) .
C13 H13 0.9300 .
C14 C15 1.436(5) .
C14 C19 1.451(5) .
C15 C20 1.397(5) .
C15 S1 1.743(3) .
S1 C16 1.732(4) .
C16 C19 1.364(5) .
C16 C17 1.413(5) .
C17 C18 1.342(6) .
C17 H17 0.9300 .
C18 S2 1.713(5) .
C18 H18 0.9300 .
S2 C19 1.719(4) .
C20 C21 1.419(6) .
C20 C22 1.421(6) .
C21 N1 1.139(5) .
C22 N2 1.137(6) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11B O1 0.96 2.53 2.859(5) 100.3 .
C12 H12 S2 0.93 2.53 3.280(4) 138.1 .
C18 H18 N1 0.93 2.49 3.324(6) 150.0 4_465
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_4
C5 O1 C1 C2 0.000(2) .
C5 O1 C1 C6 180.000(1) .
O1 C1 C2 C3 0.000(2) .
C6 C1 C2 C3 180.000(1) .
C1 C2 C3 C12 180.000(1) .
C1 C2 C3 C4 0.000(1) .
C12 C3 C4 C5 180.000(2) .
C2 C3 C4 C5 0.000(2) .
C3 C4 C5 O1 0.000(2) .
C3 C4 C5 C9 180.000(2) .
C1 O1 C5 C4 0.000(2) .
C1 O1 C5 C9 180.000(2) .
C2 C1 C6 C8 0.000(2) .
O1 C1 C6 C8 180.000(1) .
C2 C1 C6 C7 119.7(3) .
O1 C1 C6 C7 -60.3(3) .
C2 C1 C6 C7 -119.7(3) 4_565
O1 C1 C6 C7 60.3(3) 4_565
C4 C5 C9 C10 0.000(2) .
O1 C5 C9 C10 180.000(2) .
C4 C5 C9 C11 -118.2(4) .
O1 C5 C9 C11 61.8(4) .
C4 C5 C9 C11 118.2(4) 4_565
O1 C5 C9 C11 -61.8(4) 4_565
C4 C3 C12 C13 180.000(1) .
C2 C3 C12 C13 0.000(1) .
C3 C12 C13 C14 180.000(1) .
C12 C13 C14 C15 180.0 .
C12 C13 C14 C19 0.000(1) .
C13 C14 C15 C20 0.000(1) .
C19 C14 C15 C20 180.0 .
C13 C14 C15 S1 180.0 .
C19 C14 C15 S1 0.0 .
C20 C15 S1 C16 180.0 .
C14 C15 S1 C16 0.0 .
C15 S1 C16 C19 0.0 .
C15 S1 C16 C17 180.0 .
C19 C16 C17 C18 0.0 .
S1 C16 C17 C18 180.0 .
C16 C17 C18 S2 0.0 .
C17 C18 S2 C19 0.0 .
C17 C16 C19 C14 180.0 .
S1 C16 C19 C14 0.0 .
C17 C16 C19 S2 0.0 .
S1 C16 C19 S2 180.0 .
C13 C14 C19 C16 180.0 .
C15 C14 C19 C16 0.0 .
C13 C14 C19 S2 0.0 .
C15 C14 C19 S2 180.0 .
C18 S2 C19 C16 0.0 .
C18 S2 C19 C14 180.0 .
C14 C15 C20 C21 0.000(1) .
S1 C15 C20 C21 180.0 .
C14 C15 C20 C22 180.0 .
S1 C15 C20 C22 0.0 .
