#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:01:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178456 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/77/4027763.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_4027763
loop_
_publ_author_name
'Raúl García'
'M Ángeles Herranz'
'M Rosario Torres'
'Pierre-Antoine Bouit'
'Juan Luis Delgado'
'Joaquín Calbo'
'Pedro M. Viruela'
'Enrique Ortí'
'Nazario Martín'
_publ_section_title
;
 Tuning the Electronic Properties of Nonplanar exTTF-Based Push-Pull
 Chromophores by Aryl Substitution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10707
_journal_page_last               10717
_journal_paper_doi               10.1021/jo302047m
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C48 H20 N8 S4 . 2(C1 H2 Cl2)'
_chemical_formula_sum            'C50 H24 Cl4 N8 S4'
_chemical_formula_weight         1006.81
_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                90.00
_cell_angle_beta                 104.835(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   33.413(3)
_cell_length_b                   9.4529(8)
_cell_length_c                   15.7550(13)
_cell_measurement_reflns_used    2056
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.61
_cell_measurement_theta_min      2.24
_cell_volume                     4810.3(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0873
_diffrn_reflns_av_sigmaI/netI    0.1360
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21014
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.258
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5223
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1995
_refine_ls_R_factor_gt           0.0844
_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)+(0.1700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2614
_refine_ls_wR_factor_ref         0.3264
_reflns_number_gt                1906
_reflns_number_total             5223
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo302047m_si_001.cif
_cod_data_source_block           rg282
_cod_original_cell_volume        4810.4(7)
_cod_database_code               4027763
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
C1 C 0.4426(3) 0.3392(8) -0.0399(5) 0.072(2) Uani 1 1 d .
H1 H 0.4235 0.3994 -0.0756 0.087 Uiso 1 1 calc R
C2 C 0.4809(3) 0.3373(9) -0.0431(5) 0.073(2) Uani 1 1 d .
H2 H 0.4902 0.3965 -0.0812 0.088 Uiso 1 1 calc R
C3 C 0.47835(17) 0.1625(7) 0.0824(4) 0.0431(15) Uani 1 1 d .
C4 C 0.48857(16) 0.0850(6) 0.1576(3) 0.0378(14) Uani 1 1 d .
C5 C 0.45734(16) 0.0421(6) 0.2048(4) 0.0356(13) Uani 1 1 d .
C6 C 0.46928(15) 0.0409(6) 0.2986(3) 0.0352(13) Uani 1 1 d .
C7 C 0.44064(16) -0.0010(7) 0.3425(4) 0.0409(15) Uani 1 1 d .
H7 H 0.4483 -0.0030 0.4035 0.049 Uiso 1 1 calc R
C8 C 0.40060(18) -0.0405(7) 0.2983(4) 0.0464(16) Uani 1 1 d .
H8 H 0.3818 -0.0667 0.3301 0.056 Uiso 1 1 calc R
C9 C 0.38845(16) -0.0411(6) 0.2068(3) 0.0350(13) Uani 1 1 d .
C10 C 0.41762(16) 0.0003(6) 0.1615(4) 0.0374(14) Uani 1 1 d .
H10 H 0.4100 -0.0004 0.1005 0.045 Uiso 1 1 calc R
C11 C 0.34686(17) -0.0810(6) 0.1577(4) 0.0379(14) Uani 1 1 d .
C12 C 0.33044(15) -0.0077(6) 0.0703(3) 0.0341(13) Uani 1 1 d .
C13 C 0.31679(17) 0.1367(6) 0.0733(4) 0.0396(14) Uani 1 1 d .
C14 C 0.3032(2) 0.1847(8) 0.1444(4) 0.0554(18) Uani 1 1 d .
H14 H 0.3032 0.1237 0.1907 0.066 Uiso 1 1 calc R
C15 C 0.2898(2) 0.3222(9) 0.1471(5) 0.074(2) Uani 1 1 d .
H15 H 0.2804 0.3521 0.1948 0.089 Uiso 1 1 calc R
C16 C 0.2901(2) 0.4153(8) 0.0809(6) 0.074(2) Uani 1 1 d .
H16 H 0.2804 0.5072 0.0828 0.089 Uiso 1 1 calc R
C17 C 0.3049(2) 0.3708(8) 0.0114(5) 0.0613(19) Uani 1 1 d .
H17 H 0.3062 0.4344 -0.0328 0.074 Uiso 1 1 calc R
C18 C 0.31761(19) 0.2348(7) 0.0067(4) 0.0485(16) Uani 1 1 d .
H18 H 0.3270 0.2063 -0.0413 0.058 Uiso 1 1 calc R
C19 C 0.32120(17) -0.1734(6) 0.1843(4) 0.0406(14) Uani 1 1 d .
C20 C 0.33297(19) -0.2616(7) 0.2604(4) 0.0464(16) Uani 1 1 d D
C21 C 0.2789(2) -0.1883(7) 0.1357(4) 0.0461(16) Uani 1 1 d D
C22 C 0.33008(17) -0.0854(7) -0.0024(4) 0.0385(14) Uani 1 1 d .
C23 C 0.31314(18) -0.0392(7) -0.0904(4) 0.0447(15) Uani 1 1 d D
C24 C 0.3487(2) -0.2241(8) 0.0036(4) 0.0511(17) Uani 1 1 d D
N1 N 0.3415(2) -0.3360(7) 0.3184(4) 0.0700(18) Uani 1 1 d D
N2 N 0.24510(19) -0.1981(7) 0.0984(4) 0.0705(18) Uani 1 1 d D
N3 N 0.29901(18) -0.0074(6) -0.1623(4) 0.0606(16) Uani 1 1 d D
N4 N 0.3657(2) -0.3296(8) 0.0091(5) 0.081(2) Uani 1 1 d D
S1 S 0.42818(5) 0.2255(2) 0.03361(11) 0.0580(6) Uani 1 1 d .
S2 S 0.51431(6) 0.2210(2) 0.02572(11) 0.0643(6) Uani 1 1 d .
C25 C 0.4068 0.4908 0.1873 0.233 Uani 1 1 d D
H25A H 0.3795 0.5332 0.1754 0.279 Uiso 1 1 calc R
H25B H 0.4085 0.4379 0.1356 0.279 Uiso 1 1 calc R
Cl1 Cl 0.4440 0.6263 0.2054 0.258 Uani 1 1 d D
Cl2 Cl 0.4125 0.3735 0.2753 0.251 Uani 1 1 d 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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C2 C1 S1 117.6(6) . .
C2 C1 H1 121.2 . .
S1 C1 H1 121.2 . .
C1 C2 S2 118.0(6) . .
C1 C2 H2 121.0 . .
S2 C2 H2 121.0 . .
C4 C3 S2 124.0(5) . .
C4 C3 S1 124.2(5) . .
S2 C3 S1 111.7(3) . .
C3 C4 C6 124.2(5) . 2_655
C3 C4 C5 122.1(5) . .
C6 C4 C5 113.7(5) 2_655 .
C10 C5 C6 119.0(5) . .
C10 C5 C4 122.7(5) . .
C6 C5 C4 118.3(5) . .
C7 C6 C5 118.4(5) . .
C7 C6 C4 123.7(5) . 2_655
C5 C6 C4 117.8(5) . 2_655
C6 C7 C8 122.0(5) . .
C6 C7 H7 119.0 . .
C8 C7 H7 119.0 . .
C7 C8 C9 120.4(5) . .
C7 C8 H8 119.8 . .
C9 C8 H8 119.8 . .
C8 C9 C10 117.9(5) . .
C8 C9 C11 122.4(5) . .
C10 C9 C11 119.7(5) . .
C5 C10 C9 122.2(5) . .
C5 C10 H10 118.9 . .
C9 C10 H10 118.9 . .
C19 C11 C9 126.3(5) . .
C19 C11 C12 117.6(5) . .
C9 C11 C12 116.0(5) . .
C22 C12 C13 127.2(5) . .
C22 C12 C11 116.3(5) . .
C13 C12 C11 116.5(5) . .
C14 C13 C18 117.4(6) . .
C14 C13 C12 120.5(6) . .
C18 C13 C12 122.1(5) . .
C15 C14 C13 120.5(7) . .
C15 C14 H14 119.7 . .
C13 C14 H14 119.7 . .
C16 C15 C14 121.3(7) . .
C16 C15 H15 119.4 . .
C14 C15 H15 119.4 . .
C15 C16 C17 118.9(7) . .
C15 C16 H16 120.5 . .
C17 C16 H16 120.5 . .
C18 C17 C16 120.8(7) . .
C18 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C17 C18 C13 121.0(6) . .
C17 C18 H18 119.5 . .
C13 C18 H18 119.5 . .
C11 C19 C21 120.7(5) . .
C11 C19 C20 124.9(5) . .
C21 C19 C20 114.5(5) . .
N1 C20 C19 177.0(7) . .
N2 C21 C19 178.4(8) . .
C12 C22 C23 124.7(6) . .
C12 C22 C24 121.6(5) . .
C23 C22 C24 113.6(5) . .
N3 C23 C22 177.2(7) . .
N4 C24 C22 175.7(7) . .
C1 S1 C3 96.0(4) . .
C2 S2 C3 95.8(3) . .
Cl2 C25 Cl1 114.0 . .
Cl2 C25 H25A 108.8 . .
Cl1 C25 H25A 108.8 . .
Cl2 C25 H25B 108.8 . .
Cl1 C25 H25B 108.8 . .
H25A C25 H25B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.293(10) .
C1 S1 1.736(8) .
C1 H1 0.9300 .
C2 S2 1.736(8) .
C2 H2 0.9300 .
C3 C4 1.360(8) .
C3 S2 1.760(6) .
C3 S1 1.759(6) .
C4 C6 1.462(7) 2_655
C4 C5 1.484(7) .
C5 C10 1.385(7) .
C5 C6 1.429(8) .
C6 C7 1.375(7) .
C6 C4 1.462(7) 2_655
C7 C8 1.392(7) .
C7 H7 0.9300 .
C8 C9 1.395(8) .
C8 H8 0.9300 .
C9 C10 1.402(7) .
C9 C11 1.456(7) .
C10 H10 0.9300 .
C11 C19 1.363(8) .
C11 C12 1.513(7) .
C12 C22 1.359(8) .
C12 C13 1.444(8) .
C13 C14 1.387(8) .
C13 C18 1.406(8) .
C14 C15 1.379(10) .
C14 H14 0.9300 .
C15 C16 1.365(11) .
C15 H15 0.9300 .
C16 C17 1.377(10) .
C16 H16 0.9300 .
C17 C18 1.363(10) .
C17 H17 0.9300 .
C18 H18 0.9300 .
C19 C21 1.430(9) .
C19 C20 1.430(9) .
C20 N1 1.130(7) .
C21 N2 1.137(7) .
C22 C23 1.425(9) .
C22 C24 1.443(10) .
C23 N3 1.150(7) .
C24 N4 1.141(8) .
C25 Cl2 1.7469 .
C25 Cl1 1.7566 .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
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
S1 C1 C2 S2 0.3(10) . .
S2 C3 C4 C6 0.4(9) . 2_655
S1 C3 C4 C6 -175.6(5) . 2_655
S2 C3 C4 C5 177.9(4) . .
S1 C3 C4 C5 1.9(9) . .
C3 C4 C5 C10 38.7(9) . .
C6 C4 C5 C10 -143.6(6) 2_655 .
C3 C4 C5 C6 -142.8(6) . .
C6 C4 C5 C6 34.9(7) 2_655 .
C10 C5 C6 C7 -0.4(8) . .
C4 C5 C6 C7 -179.0(5) . .
C10 C5 C6 C4 179.8(5) . 2_655
C4 C5 C6 C4 1.2(7) . 2_655
C5 C6 C7 C8 -0.7(9) . .
C4 C6 C7 C8 179.2(6) 2_655 .
C6 C7 C8 C9 1.2(10) . .
C7 C8 C9 C10 -0.5(9) . .
C7 C8 C9 C11 -179.7(6) . .
C6 C5 C10 C9 1.0(8) . .
C4 C5 C10 C9 179.5(5) . .
C8 C9 C10 C5 -0.6(9) . .
C11 C9 C10 C5 178.6(5) . .
C8 C9 C11 C19 -29.3(9) . .
C10 C9 C11 C19 151.6(6) . .
C8 C9 C11 C12 148.3(6) . .
C10 C9 C11 C12 -30.8(8) . .
C19 C11 C12 C22 -78.2(7) . .
C9 C11 C12 C22 104.0(6) . .
C19 C11 C12 C13 101.6(6) . .
C9 C11 C12 C13 -76.2(6) . .
C22 C12 C13 C14 154.0(6) . .
C11 C12 C13 C14 -25.8(8) . .
C22 C12 C13 C18 -27.8(9) . .
C11 C12 C13 C18 152.5(5) . .
C18 C13 C14 C15 2.2(10) . .
C12 C13 C14 C15 -179.4(6) . .
C13 C14 C15 C16 -1.0(12) . .
C14 C15 C16 C17 -1.4(12) . .
C15 C16 C17 C18 2.5(11) . .
C16 C17 C18 C13 -1.3(10) . .
C14 C13 C18 C17 -1.1(9) . .
C12 C13 C18 C17 -179.4(6) . .
C9 C11 C19 C21 171.0(6) . .
C12 C11 C19 C21 -6.6(8) . .
C9 C11 C19 C20 -8.9(10) . .
C12 C11 C19 C20 173.6(6) . .
C11 C19 C20 N1 -131(14) . .
C21 C19 C20 N1 49(15) . .
C11 C19 C21 N2 -99(27) . .
C20 C19 C21 N2 80(27) . .
C13 C12 C22 C23 -4.5(9) . .
C11 C12 C22 C23 175.3(5) . .
C13 C12 C22 C24 173.4(5) . .
C11 C12 C22 C24 -6.9(8) . .
C12 C22 C23 N3 -147(14) . .
C24 C22 C23 N3 35(14) . .
C12 C22 C24 N4 -80(10) . .
C23 C22 C24 N4 98(10) . .
C2 C1 S1 C3 5.2(7) . .
C4 C3 S1 C1 168.0(6) . .
S2 C3 S1 C1 -8.4(4) . .
C1 C2 S2 C3 -5.6(7) . .
C4 C3 S2 C2 -167.9(6) . .
S1 C3 S2 C2 8.5(4) . .
