#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:35:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178906 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113537.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_4113537
loop_
_publ_author_name
'Michel Guerro'
'Roger Carlier'
'Kamal Boubekeur'
'Dominique Lorcy'
'Philippe Hapiot'
_publ_section_title
;
 Cyclic Vinylogous TTF: a Potential Molecular Clip Triggered by Electron
 Transfer
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3159
_journal_page_last               3167
_journal_paper_doi               10.1021/ja0289090
_journal_volume                  125
_journal_year                    2003
_chemical_formula_moiety         'C27 H20 N2 S6 , 0.5(C H2 CL2)'
_chemical_formula_sum            'C55 H42 Cl2 N4 S12'
_chemical_formula_weight         1214.55
_chemical_name_common            (C27H20N2S6).(CH2CL2)0.5
_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                 90.790(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.3213(10)
_cell_length_b                   12.8455(9)
_cell_length_c                   20.754(2)
_cell_measurement_reflns_used    2000
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      1.86
_cell_volume                     3017.9(4)
_computing_cell_refinement       'SELECT (Stoe IPDS)'
_computing_data_collection       'EXPOSE (Stoe IPDS)'
_computing_data_reduction        'INTEGRATE (Stoe IPDS)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'Rotation, Δφ=1.%'
_diffrn_radiation_detector       'area detector'
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            21226
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       plate
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_refine_diff_density_max         1.260
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6572
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0719
_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)+(0.1579P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2029
_refine_ls_wR_factor_ref         0.2188
_reflns_number_gt                3998
_reflns_number_total             6572
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0289090si20021220_104545_3.cif
_cod_data_source_block           2a(3)
_cod_original_cell_volume        3018.0(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4113537
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 0.62265(12) 0.14421(12) 0.24889(7) 0.0600(4) Uani 1 1 d .
S2 S 0.53790(14) 0.13451(13) 0.38068(7) 0.0659(5) Uani 1 1 d .
S3 S 0.51806(13) -0.07585(13) 0.10104(7) 0.0636(5) Uani 1 1 d .
S4 S 0.60963(12) -0.10998(12) 0.23062(7) 0.0583(4) Uani 1 1 d .
S5 S 0.86983(14) 0.20113(15) 0.28717(10) 0.0832(6) Uani 1 1 d .
S6 S 0.85387(14) -0.16651(15) 0.18697(10) 0.0787(6) Uani 1 1 d .
C1 C 0.5103(4) 0.1004(4) 0.2998(3) 0.0520(13) Uani 1 1 d .
C2 C 0.7244(5) 0.1742(5) 0.3106(3) 0.0643(16) Uani 1 1 d .
C3 C 0.6858(5) 0.1705(5) 0.3717(3) 0.0683(17) Uani 1 1 d .
C4 C 0.9445(6) 0.0807(6) 0.3115(4) 0.088(2) Uani 1 1 d .
H4A H 1.0254 0.0847 0.2969 0.106 Uiso 1 1 calc R
H4B H 0.9475 0.0791 0.3582 0.106 Uiso 1 1 calc R
C5 C 0.8933(6) -0.0239(6) 0.2883(4) 0.087(2) Uani 1 1 d .
H5A H 0.9296 -0.0798 0.3130 0.104 Uiso 1 1 calc R
H5B H 0.8092 -0.0251 0.2965 0.104 Uiso 1 1 calc R
C6 C 0.9131(6) -0.0427(7) 0.2178(4) 0.098(2) Uani 1 1 d .
H6A H 0.9974 -0.0409 0.2100 0.117 Uiso 1 1 calc R
H6B H 0.8772 0.0138 0.1935 0.117 Uiso 1 1 calc R
C7 C 0.7087(5) -0.1288(5) 0.1667(3) 0.0628(15) Uani 1 1 d .
C8 C 0.6665(5) -0.1141(5) 0.1082(3) 0.0633(15) Uani 1 1 d .
C9 C 0.4989(4) -0.0531(4) 0.1838(2) 0.0517(13) Uani 1 1 d .
C10 C 0.4106(4) 0.0068(4) 0.2093(2) 0.0488(12) Uani 1 1 d .
C11 C 0.4186(4) 0.0408(4) 0.2786(2) 0.0469(12) Uani 1 1 d .
C12 C 0.3220(4) 0.0068(4) 0.3213(2) 0.0469(12) Uani 1 1 d .
C13 C 0.2782(5) 0.0689(5) 0.3697(3) 0.0582(14) Uani 1 1 d .
H13 H 0.3081 0.1357 0.3756 0.070 Uiso 1 1 calc R
C14 C 0.1904(5) 0.0328(5) 0.4097(3) 0.0650(15) Uani 1 1 d .
H14 H 0.1619 0.0754 0.4422 0.078 Uiso 1 1 calc R
C15 C 0.1451(5) -0.0655(5) 0.4016(3) 0.0555(13) Uani 1 1 d .
C16 C 0.1868(5) -0.1283(5) 0.3526(3) 0.0607(14) Uani 1 1 d .
H16 H 0.1563 -0.1949 0.3467 0.073 Uiso 1 1 calc R
C17 C 0.2736(5) -0.0919(4) 0.3124(3) 0.0556(13) Uani 1 1 d .
H17 H 0.3001 -0.1337 0.2790 0.067 Uiso 1 1 calc R
C18 C 0.0504(6) -0.1024(6) 0.4405(3) 0.0722(17) Uani 1 1 d .
C19 C 0.3049(4) 0.0370(4) 0.1725(2) 0.0478(12) Uani 1 1 d .
C20 C 0.2511(5) -0.0313(5) 0.1295(3) 0.0583(14) Uani 1 1 d .
H20 H 0.2849 -0.0963 0.1226 0.070 Uiso 1 1 calc R
C21 C 0.1481(5) -0.0050(5) 0.0965(3) 0.0615(15) Uani 1 1 d .
H21 H 0.1136 -0.0518 0.0678 0.074 Uiso 1 1 calc R
C22 C 0.0975(5) 0.0905(5) 0.1066(3) 0.0590(14) Uani 1 1 d .
C23 C 0.1493(6) 0.1596(5) 0.1500(3) 0.0694(17) Uani 1 1 d .
H23 H 0.1150 0.2244 0.1567 0.083 Uiso 1 1 calc R
C24 C 0.2498(5) 0.1332(5) 0.1827(3) 0.0639(15) Uani 1 1 d .
H24 H 0.2824 0.1797 0.2123 0.077 Uiso 1 1 calc R
C25 C -0.0138(6) 0.1160(5) 0.0745(3) 0.0735(17) Uani 1 1 d .
C26 C 0.7571(7) 0.1910(6) 0.4317(4) 0.094(2) Uani 1 1 d .
H26A H 0.7735 0.1263 0.4532 0.141 Uiso 1 1 calc R
H26B H 0.7133 0.2356 0.4598 0.141 Uiso 1 1 calc R
H26C H 0.8300 0.2241 0.4206 0.141 Uiso 1 1 calc R
C27 C 0.7314(7) -0.1245(7) 0.0449(4) 0.093(2) Uani 1 1 d .
H27A H 0.7215 -0.0618 0.0202 0.139 Uiso 1 1 calc R
H27B H 0.6998 -0.1823 0.0210 0.139 Uiso 1 1 calc R
H27C H 0.8139 -0.1359 0.0535 0.139 Uiso 1 1 calc R
N1 N -0.0286(6) -0.1304(6) 0.4698(3) 0.102(2) Uani 1 1 d .
N2 N -0.1024(6) 0.1328(6) 0.0496(4) 0.105(2) Uani 1 1 d .
Cl1 Cl 0.5241(4) 0.2243(3) 0.0716(2) 0.0965(12) Uani 0.50 1 d P
Cl2 Cl 0.3274(4) 0.3704(3) 0.0653(2) 0.0980(13) Uani 0.50 1 d P
C28 C 0.4697(12) 0.3458(13) 0.0837(8) 0.093(5) Uani 0.50 1 d P
H28A H 0.5175 0.3939 0.0591 0.111 Uiso 0.50 1 calc PR
H28B H 0.4820 0.3627 0.1289 0.111 Uiso 0.50 1 calc PR
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
C2 S1 C1 96.0(3)
C3 S2 C1 97.0(3)
C8 S3 C9 95.4(3)
C9 S4 C7 95.6(3)
C2 S5 C4 100.8(3)
C7 S6 C6 100.4(3)
C11 C1 S2 125.1(4)
C11 C1 S1 122.8(4)
S2 C1 S1 111.9(3)
C3 C2 S1 117.4(4)
C3 C2 S5 125.8(5)
S1 C2 S5 116.7(4)
C2 C3 C26 126.7(6)
C2 C3 S2 115.7(4)
C26 C3 S2 117.5(6)
C5 C4 S5 118.8(5)
C6 C5 C4 112.6(7)
C5 C6 S6 114.8(5)
C8 C7 S6 126.0(5)
C8 C7 S4 116.7(5)
S6 C7 S4 117.3(4)
C7 C8 C27 127.8(6)
C7 C8 S3 117.0(5)
C27 C8 S3 115.2(5)
C10 C9 S4 122.9(4)
C10 C9 S3 124.7(4)
S4 C9 S3 112.3(3)
C9 C10 C19 122.8(5)
C9 C10 C11 119.8(4)
C19 C10 C11 117.4(4)
C1 C11 C12 122.6(5)
C1 C11 C10 120.6(4)
C12 C11 C10 116.8(4)
C13 C12 C17 118.5(5)
C13 C12 C11 122.7(5)
C17 C12 C11 118.8(5)
C12 C13 C14 120.8(6)
C15 C14 C13 120.3(5)
C14 C15 C16 119.6(5)
C14 C15 C18 121.1(5)
C16 C15 C18 119.2(6)
C17 C16 C15 120.0(5)
C16 C17 C12 120.7(5)
N1 C18 C15 177.1(8)
C20 C19 C24 117.6(5)
C20 C19 C10 121.1(5)
C24 C19 C10 121.2(5)
C19 C20 C21 121.5(5)
C22 C21 C20 119.6(5)
C21 C22 C23 119.8(5)
C21 C22 C25 119.5(5)
C23 C22 C25 120.6(6)
C24 C23 C22 120.5(6)
C23 C24 C19 121.0(5)
N2 C25 C22 177.8(8)
Cl1 C28 Cl2 119.2(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.754(6)
S1 C1 1.758(6)
S2 C3 1.749(6)
S2 C1 1.758(5)
S3 C8 1.756(6)
S3 C9 1.758(5)
S4 C9 1.737(5)
S4 C7 1.766(6)
S5 C2 1.758(6)
S5 C4 1.831(8)
S6 C7 1.759(6)
S6 C6 1.837(9)
C1 C11 1.358(7)
C2 C3 1.347(9)
C3 C26 1.499(9)
C4 C5 1.537(10)
C5 C6 1.504(11)
C7 C8 1.311(9)
C8 C27 1.520(9)
C9 C10 1.373(7)
C10 C19 1.464(7)
C10 C11 1.505(7)
C11 C12 1.483(7)
C12 C13 1.380(7)
C12 C17 1.392(7)
C13 C14 1.383(8)
C14 C15 1.373(9)
C15 C16 1.386(8)
C15 C18 1.432(8)
C16 C17 1.378(8)
C18 N1 1.146(8)
C19 C20 1.386(7)
C19 C24 1.401(8)
C20 C21 1.385(8)
C21 C22 1.371(8)
C22 C23 1.388(8)
C22 C25 1.455(8)
C23 C24 1.360(8)
C25 N2 1.142(8)
Cl1 C28 1.698(16)
Cl2 C28 1.681(14)
