#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/68/4026848.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_4026848
loop_
_publ_author_name
'Vasily A. Migulin'
'Michael M. Krayushkin'
'Valery A. Barachevsky'
'Olga I. Kobeleva'
'Tatyana M. Valova'
'Konstantin A. Lyssenko'
_publ_section_title
;
 Synthesis and Characterization of Nonsymmetric Cyclopentene-Based
 Dithienylethenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              332
_journal_page_last               340
_journal_paper_doi               10.1021/jo201966g
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C20 H20 S2'
_chemical_formula_sum            'C20 H20 S2'
_chemical_formula_weight         324.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                90.00
_cell_angle_beta                 97.4242(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3268(8)
_cell_length_b                   13.2672(11)
_cell_length_c                   15.4463(13)
_cell_measurement_reflns_used    497
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29
_cell_measurement_theta_min      3
_cell_volume                     1692.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector''
_diffrn_measurement_method       '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  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13205
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.309
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0407
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0774P)²+0.7388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1254
_reflns_number_gt                3669
_reflns_number_total             4476
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo201966g_si_003.cif
_cod_data_source_block           a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.35089(5) 0.03201(3) 0.17443(3) 0.03442(12) Uani 1 1 d .
S1" S 0.36296(6) 0.33362(3) 0.46478(3) 0.04277(13) Uani 1 1 d .
C2' C 0.19456(17) 0.09679(11) 0.21583(10) 0.0298(3) Uani 1 1 d .
C3' C 0.13669(17) 0.04532(11) 0.28166(9) 0.0279(3) Uani 1 1 d .
C3A' C 0.21993(17) -0.04916(11) 0.30078(9) 0.0278(3) Uani 1 1 d .
C2 C -0.01555(19) 0.16505(13) 0.36909(10) 0.0339(3) Uani 1 1 d .
C7A' C 0.34303(18) -0.06562(11) 0.24797(10) 0.0289(3) Uani 1 1 d .
C1 C -0.00154(18) 0.07937(13) 0.32476(10) 0.0325(3) Uani 1 1 d .
C4' C 0.1975(2) -0.12130(13) 0.36441(10) 0.0357(3) Uani 1 1 d .
H4'A H 0.1155 -0.1122 0.4011 0.043 Uiso 1 1 calc R
C6' C 0.4165(2) -0.22012(13) 0.32048(11) 0.0403(4) Uani 1 1 d .
H6'A H 0.4824 -0.2787 0.3280 0.048 Uiso 1 1 calc R
C7' C 0.4423(2) -0.15082(12) 0.25743(11) 0.0358(3) Uani 1 1 d .
H7'A H 0.5252 -0.1606 0.2214 0.043 Uiso 1 1 calc R
C8' C 0.1400(2) 0.19579(13) 0.17674(12) 0.0397(4) Uani 1 1 d .
H8'A H 0.0334 0.2126 0.1932 0.060 Uiso 1 1 calc R
H8'B H 0.1328 0.1916 0.1130 0.060 Uiso 1 1 calc R
H8'C H 0.2180 0.2482 0.1983 0.060 Uiso 1 1 calc R
C2" C 0.2610(2) 0.22293(13) 0.43668(10) 0.0358(3) Uani 1 1 d .
C5' C 0.2953(2) -0.20553(13) 0.37329(11) 0.0398(4) Uani 1 1 d .
H5'A H 0.2795 -0.2545 0.4163 0.048 Uiso 1 1 calc R
C3" C 0.1074(2) 0.24190(12) 0.39643(10) 0.0348(3) Uani 1 1 d .
C8"H C 0.3385(2) 0.12347(15) 0.46251(14) 0.0485(5) Uani 1 1 d .
H8"A H 0.2542 0.0738 0.4700 0.073 Uiso 1 1 calc R
H8"B H 0.4104 0.1311 0.5175 0.073 Uiso 1 1 calc R
H8"C H 0.4013 0.1005 0.4168 0.073 Uiso 1 1 calc R
C5 C -0.1558(2) 0.01714(19) 0.31714(14) 0.0555(5) Uani 1 1 d .
H5A H -0.1947 0.0013 0.2553 0.067 Uiso 1 1 calc R
H5B H -0.1383 -0.0466 0.3503 0.067 Uiso 1 1 calc R
C3A" C 0.0749(2) 0.34846(14) 0.39069(11) 0.0438(4) Uani 1 1 d .
H3AA H -0.0262 0.3751 0.3653 0.053 Uiso 1 1 calc R
C7"H C 0.2094(4) 0.52039(15) 0.42974(15) 0.0654(7) Uani 1 1 d .
H7"A H 0.1090 0.5497 0.4002 0.098 Uiso 1 1 calc R
H7"B H 0.3012 0.5440 0.4014 0.098 Uiso 1 1 calc R
H7"C H 0.2244 0.5411 0.4911 0.098 Uiso 1 1 calc R
C7A" C 0.1998(3) 0.40739(14) 0.42432(11) 0.0467(4) Uani 1 1 d .
C3 C -0.1854(2) 0.17610(18) 0.39306(12) 0.0521(5) Uani 1 1 d .
H3A H -0.1836 0.1788 0.4572 0.063 Uiso 1 1 calc R
H3C H -0.2372 0.2382 0.3672 0.063 Uiso 1 1 calc R
C4 C -0.2747(3) 0.0843(2) 0.3560(2) 0.0710(8) Uani 1 1 d .
H4C H -0.3637 0.1042 0.3105 0.085 Uiso 1 1 calc R
H4A H -0.3219 0.0479 0.4027 0.085 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'
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
C7A' S1' C2' 91.99(7)
C2" S1" C7A" 93.03(9)
C3' C2' C8' 128.64(14)
C3' C2' S1' 112.22(11)
C8' C2' S1' 119.13(12)
C2' C3' C3A' 112.37(13)
C2' C3' C1 123.75(14)
C3A' C3' C1 123.78(13)
C4' C3A' C7A' 118.28(14)
C4' C3A' C3' 129.20(14)
C7A' C3A' C3' 112.49(13)
C1 C2 C3" 129.26(14)
C1 C2 C3 110.65(16)
C3" C2 C3 120.07(15)
C7' C7A' C3A' 122.04(14)
C7' C7A' S1' 127.06(12)
C3A' C7A' S1' 110.90(11)
C2 C1 C3' 128.01(15)
C2 C1 C5 111.85(15)
C3' C1 C5 120.04(15)
C5' C4' C3A' 119.50(16)
C5' C4' H4'A 120.2
C3A' C4' H4'A 120.2
C7' C6' C5' 120.89(16)
C7' C6' H6'A 119.6
C5' C6' H6'A 119.6
C6' C7' C7A' 118.07(16)
C6' C7' H7'A 121.0
C7A' C7' H7'A 121.0
C2' C8' H8'A 109.5
C2' C8' H8'B 109.5
H8'A C8' H8'B 109.5
C2' C8' H8'C 109.5
H8'A C8' H8'C 109.5
H8'B C8' H8'C 109.5
C3" C2" C8"H 128.73(16)
C3" C2" S1" 110.98(13)
C8"H C2" S1" 120.13(13)
C4' C5' C6' 121.22(16)
C4' C5' H5'A 119.4
C6' C5' H5'A 119.4
C2" C3" C3A" 111.40(16)
C2" C3" C2 125.31(15)
C3A" C3" C2 123.09(15)
C2" C8"H H8"A 109.5
C2" C8"H H8"B 109.5
H8"A C8"H H8"B 109.5
C2" C8"H H8"C 109.5
H8"A C8"H H8"C 109.5
H8"B C8"H H8"C 109.5
C4 C5 C1 103.84(18)
C4 C5 H5A 111.0
C1 C5 H5A 111.0
C4 C5 H5B 111.0
C1 C5 H5B 111.0
H5A C5 H5B 109.0
C7A" C3A" C3" 114.57(16)
C7A" C3A" H3AA 122.7
C3" C3A" H3AA 122.7
C7A" C7"H H7"A 109.5
C7A" C7"H H7"B 109.5
H7"A C7"H H7"B 109.5
C7A" C7"H H7"C 109.5
H7"A C7"H H7"C 109.5
H7"B C7"H H7"C 109.5
C3A" C7A" C7"H 129.21(19)
C3A" C7A" S1" 110.02(14)
C7"H C7A" S1" 120.78(17)
C4 C3 C2 105.09(16)
C4 C3 H3A 110.7
C2 C3 H3A 110.7
C4 C3 H3C 110.7
C2 C3 H3C 110.7
H3A C3 H3C 108.8
C3 C4 C5 108.20(16)
C3 C4 H4C 110.1
C5 C4 H4C 110.1
C3 C4 H4A 110.1
C5 C4 H4A 110.1
H4C C4 H4A 108.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1' C7A' 1.7297(16)
S1' C2' 1.7485(15)
S1" C2" 1.7234(18)
S1" C7A" 1.725(2)
C2' C3' 1.363(2)
C2' C8' 1.492(2)
C3' C3A' 1.444(2)
C3' C1 1.473(2)
C3A' C4' 1.402(2)
C3A' C7A' 1.407(2)
C2 C1 1.340(2)
C2 C3" 1.468(2)
C2 C3 1.515(2)
C7A' C7' 1.397(2)
C1 C5 1.519(2)
C4' C5' 1.379(2)
C4' H4'A 0.9500
C6' C7' 1.376(2)
C6' C5' 1.391(3)
C6' H6'A 0.9500
C7' H7'A 0.9500
C8' H8'A 0.9800
C8' H8'B 0.9800
C8' H8'C 0.9800
C2" C3" 1.372(2)
C2" C8"H 1.500(2)
C5' H5'A 0.9500
C3" C3A" 1.440(2)
C8"H H8"A 0.9800
C8"H H8"B 0.9800
C8"H H8"C 0.9800
C5 C4 1.513(3)
C5 H5A 0.9900
C5 H5B 0.9900
C3A" C7A" 1.350(3)
C3A" H3AA 0.9500
C7"H C7A" 1.503(3)
C7"H H7"A 0.9800
C7"H H7"B 0.9800
C7"H H7"C 0.9800
C3 C4 1.501(4)
C3 H3A 0.9900
C3 H3C 0.9900
C4 H4C 0.9900
C4 H4A 0.9900
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
C7A' S1' C2' C3' -1.18(12)
C7A' S1' C2' C8' 179.78(13)
C8' C2' C3' C3A' 179.33(15)
S1' C2' C3' C3A' 0.40(16)
C8' C2' C3' C1 2.8(3)
S1' C2' C3' C1 -176.16(11)
C2' C3' C3A' C4' 178.64(15)
C1 C3' C3A' C4' -4.8(2)
C2' C3' C3A' C7A' 0.86(18)
C1 C3' C3A' C7A' 177.42(13)
C4' C3A' C7A' C7' -0.2(2)
C3' C3A' C7A' C7' 177.89(13)
C4' C3A' C7A' S1' -179.77(11)
C3' C3A' C7A' S1' -1.72(15)
C2' S1' C7A' C7' -177.94(14)
C2' S1' C7A' C3A' 1.64(11)
C3" C2 C1 C3' -8.5(3)
C3 C2 C1 C3' 172.96(15)
C3" C2 C1 C5 175.01(16)
C3 C2 C1 C5 -3.5(2)
C2' C3' C1 C2 -60.4(2)
C3A' C3' C1 C2 123.41(18)
C2' C3' C1 C5 115.80(19)
C3A' C3' C1 C5 -60.4(2)
C7A' C3A' C4' C5' -0.1(2)
C3' C3A' C4' C5' -177.79(15)
C5' C6' C7' C7A' -0.1(2)
C3A' C7A' C7' C6' 0.3(2)
S1' C7A' C7' C6' 179.82(12)
C7A" S1" C2" C3" 0.81(14)
C7A" S1" C2" C8"H -174.97(15)
C3A' C4' C5' C6' 0.3(2)
C7' C6' C5' C4' -0.2(3)
C8"H C2" C3" C3A" 174.33(17)
S1" C2" C3" C3A" -0.99(18)
C8"H C2" C3" C2 -0.6(3)
S1" C2" C3" C2 -175.89(12)
C1 C2 C3" C2" -47.4(3)
C3 C2 C3" C2" 130.99(18)
C1 C2 C3" C3A" 138.26(18)
C3 C2 C3" C3A" -43.3(2)
C2 C1 C5 C4 5.9(2)
C3' C1 C5 C4 -170.89(17)
C2" C3" C3A" C7A" 0.7(2)
C2 C3" C3A" C7A" 175.76(15)
C3" C3A" C7A" C7"H -179.9(2)
C3" C3A" C7A" S1" -0.1(2)
C2" S1" C7A" C3A" -0.40(15)
C2" S1" C7A" C7"H 179.42(18)
C1 C2 C3 C4 -0.4(2)
C3" C2 C3 C4 -179.10(16)
C2 C3 C4 C5 4.1(2)
C1 C5 C4 C3 -5.9(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659443
