#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:35:40 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178906 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/35/4113536.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_4113536
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         'C28 H22 N2 S6 , C2 H3 N'
_chemical_formula_structural     '(C28H22N2S6) (CH3CN)'
_chemical_formula_sum            'C30 H25 N3 S6'
_chemical_formula_weight         619.89
_chemical_name_common            (C28H22N2S6).(MeCN)
_chemical_name_systematic
; 
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.699(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8332(10)
_cell_length_b                   10.1122(11)
_cell_length_c                   24.0994(18)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.65
_cell_volume                     3073.1(5)
_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      298(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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  0.0437
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            25839
_diffrn_reflns_theta_full        25.93
_diffrn_reflns_theta_max         25.93
_diffrn_reflns_theta_min         2.19
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.470
_exptl_absorpt_correction_T_max  0.7953
_exptl_absorpt_correction_T_min  0.6655
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'FACEIT (Stoe IPDS)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       polyhedral
_exptl_crystal_F_000             1288
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5669
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0379
_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)+(0.0759P)²+0.1137P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1108
_reflns_number_gt                4658
_reflns_number_total             5669
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0289090si20021220_104545_2.cif
_cod_data_source_block           2b(4)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4113536
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30630(4) 0.09369(5) 0.23169(2) 0.05041(14) Uani 1 1 d . . .
S2 S 0.15643(4) 0.26325(5) 0.15829(2) 0.04811(14) Uani 1 1 d . . .
S3 S 0.17699(5) 0.08727(6) 0.32376(2) 0.05856(16) Uani 1 1 d . . .
S4 S 0.65753(5) 0.12055(7) 0.22618(2) 0.06708(18) Uani 1 1 d . . .
S5 S 0.51144(5) 0.33571(6) 0.23877(2) 0.05971(16) Uani 1 1 d . . .
S6 S 0.63337(5) 0.42186(7) 0.35134(3) 0.0737(2) Uani 1 1 d . . .
N1 N 0.1447(2) 0.0445(2) 0.03480(10) 0.0807(6) Uani 1 1 d . . .
N2 N 0.6782(2) 0.2685(3) 0.08692(13) 0.0980(8) Uani 1 1 d . . .
C1 C 0.28341(15) 0.19191(17) 0.17055(7) 0.0400(4) Uani 1 1 d . . .
C2 C 0.35751(14) 0.21000(16) 0.13830(7) 0.0388(4) Uani 1 1 d . . .
C3 C 0.46563(15) 0.15205(17) 0.15444(7) 0.0414(4) Uani 1 1 d . . .
C4 C 0.53523(15) 0.19607(19) 0.19960(8) 0.0475(4) Uani 1 1 d . . .
C5 C 0.19290(16) 0.14547(18) 0.25716(8) 0.0454(4) Uani 1 1 d . . .
C6 C 0.12366(16) 0.22203(18) 0.22375(8) 0.0470(4) Uani 1 1 d . . .
C7 C 0.68742(18) 0.2142(3) 0.28861(9) 0.0644(6) Uani 1 1 d . . .
C8 C 0.62005(18) 0.3118(2) 0.29397(9) 0.0590(5) Uani 1 1 d . . .
C9 C 0.02034(19) 0.2750(3) 0.23491(11) 0.0683(6) Uani 1 1 d . . .
H9A H -0.0131 0.3271 0.2033 0.102 Uiso 1 1 calc R . .
H9B H 0.0332 0.3291 0.2682 0.102 Uiso 1 1 calc R . .
H9C H -0.0252 0.2027 0.2404 0.102 Uiso 1 1 calc R . .
C10 C 0.7846(2) 0.1717(4) 0.32944(12) 0.0991(11) Uani 1 1 d . . .
H10A H 0.8167 0.0978 0.3141 0.149 Uiso 1 1 calc R . .
H10B H 0.7651 0.1464 0.3645 0.149 Uiso 1 1 calc R . .
H10C H 0.8342 0.2437 0.3358 0.149 Uiso 1 1 calc R . .
C11 C 0.3064(2) 0.1222(2) 0.36564(9) 0.0596(5) Uani 1 1 d . . .
H11A H 0.3060 0.0970 0.4044 0.072 Uiso 1 1 calc R . .
H11B H 0.3583 0.0670 0.3521 0.072 Uiso 1 1 calc R . .
C12 C 0.34228(18) 0.2656(2) 0.36492(10) 0.0569(5) Uani 1 1 d . . .
H12A H 0.3122 0.3155 0.3925 0.068 Uiso 1 1 calc R . .
H12B H 0.3156 0.3033 0.3280 0.068 Uiso 1 1 calc R . .
C13 C 0.46216(19) 0.2786(2) 0.37805(10) 0.0602(5) Uani 1 1 d . . .
H13A H 0.4874 0.2564 0.4174 0.072 Uiso 1 1 calc R . .
H13B H 0.4927 0.2156 0.3552 0.072 Uiso 1 1 calc R . .
C14 C 0.4999(2) 0.4157(2) 0.36695(11) 0.0646(6) Uani 1 1 d . . .
H14A H 0.4977 0.4704 0.3998 0.078 Uiso 1 1 calc R . .
H14B H 0.4511 0.4536 0.3354 0.078 Uiso 1 1 calc R . .
C15 C 0.33614(14) 0.28775(16) 0.08488(7) 0.0400(4) Uani 1 1 d . . .
C16 C 0.40200(18) 0.39522(17) 0.07858(9) 0.0502(5) Uani 1 1 d . . .
H16 H 0.4595 0.4145 0.1070 0.060 Uiso 1 1 calc R . .
C17 C 0.3822(2) 0.47296(19) 0.03046(10) 0.0622(6) Uani 1 1 d . . .
H17 H 0.4263 0.5444 0.0272 0.075 Uiso 1 1 calc R . .
C18 C 0.2990(2) 0.4464(2) -0.01221(10) 0.0666(7) Uani 1 1 d . . .
H18 H 0.2855 0.5012 -0.0437 0.080 Uiso 1 1 calc R . .
C19 C 0.2357(2) 0.3394(2) -0.00875(9) 0.0601(5) Uani 1 1 d . . .
H19 H 0.1802 0.3200 -0.0383 0.072 Uiso 1 1 calc R . .
C20 C 0.25491(16) 0.25862(18) 0.03970(8) 0.0452(4) Uani 1 1 d . . .
C21 C 0.19302(18) 0.1406(2) 0.03872(9) 0.0559(5) Uani 1 1 d . . .
C22 C 0.49215(15) 0.04297(17) 0.11851(7) 0.0422(4) Uani 1 1 d . . .
C23 C 0.43073(19) -0.0708(2) 0.11177(10) 0.0567(5) Uani 1 1 d . . .
H23 H 0.3741 -0.0786 0.1307 0.068 Uiso 1 1 calc R . .
C24 C 0.4521(2) -0.1728(2) 0.07745(11) 0.0695(6) Uani 1 1 d . . .
H24 H 0.4096 -0.2479 0.0733 0.083 Uiso 1 1 calc R . .
C25 C 0.5355(2) -0.1642(2) 0.04943(10) 0.0651(6) Uani 1 1 d . . .
H25 H 0.5500 -0.2340 0.0269 0.078 Uiso 1 1 calc R . .
C26 C 0.59752(18) -0.0530(2) 0.05444(8) 0.0578(5) Uani 1 1 d . . .
H26 H 0.6539 -0.0471 0.0353 0.069 Uiso 1 1 calc R . .
C27 C 0.57565(16) 0.05151(19) 0.08851(8) 0.0470(4) Uani 1 1 d . . .
C28 C 0.63438(19) 0.1724(2) 0.08899(10) 0.0621(6) Uani 1 1 d . . .
C1AS C 0.9051(3) 0.2569(5) 0.03789(18) 0.1175(13) Uani 0.50 1 d P A 1
HAS1 H 0.9314 0.1777 0.0576 0.176 Uiso 0.50 1 calc PR A 1
HAS2 H 0.9441 0.2738 0.0083 0.176 Uiso 0.50 1 calc PR A 1
HAS3 H 0.8313 0.2460 0.0219 0.176 Uiso 0.50 1 calc PR A 1
C2AS C 0.9189(5) 0.3763(7) 0.0801(4) 0.0884(18) Uani 0.50 1 d P A 1
N1AS N 0.9273(6) 0.4580(6) 0.1143(3) 0.120(2) Uani 0.50 1 d P A 1
C1BS C 0.9051(3) 0.2569(5) 0.03789(18) 0.1175(13) Uani 0.50 1 d PD B 2
HBS1 H 0.9101 0.2322 0.0768 0.176 Uiso 0.50 1 calc PR B 2
HBS2 H 0.9358 0.1887 0.0183 0.176 Uiso 0.50 1 calc PR B 2
HBS3 H 0.8319 0.2682 0.0208 0.176 Uiso 0.50 1 calc PR B 2
C2BS C 0.9558(6) 0.3672(8) 0.0349(3) 0.0927(18) Uani 0.50 1 d PD B 2
N1BS N 0.9940(8) 0.4664(8) 0.0353(5) 0.172(4) Uani 0.50 1 d PD . 2
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
_geom_angle_site_symmetry_3
C1 S1 C5 95.97(9) .
C6 S2 C1 96.95(9) .
C5 S3 C11 101.17(10) .
C4 S4 C7 96.68(10) .
C4 S5 C8 95.95(10) .
C8 S6 C14 100.53(10) .
C2 C1 S1 122.33(14) .
C2 C1 S2 125.40(14) .
S1 C1 S2 112.26(9) .
C1 C2 C3 121.25(16) .
C1 C2 C15 122.25(16) .
C3 C2 C15 116.51(14) .
C4 C3 C22 121.88(17) .
C4 C3 C2 121.74(15) .
C22 C3 C2 116.38(15) .
C3 C4 S5 122.94(15) .
C3 C4 S4 124.33(14) .
S5 C4 S4 112.72(11) .
C6 C5 S3 124.73(14) .
C6 C5 S1 117.67(13) .
S3 C5 S1 117.55(12) .
C5 C6 C9 127.76(18) .
C5 C6 S2 115.91(14) .
C9 C6 S2 116.32(17) .
C8 C7 C10 128.5(2) .
C8 C7 S4 116.02(19) .
C10 C7 S4 115.4(2) .
C7 C8 S6 125.0(2) .
C7 C8 S5 117.80(17) .
S6 C8 S5 117.13(14) .
C6 C9 H9A 109.5 .
C6 C9 H9B 109.5 .
H9A C9 H9B 109.5 .
C6 C9 H9C 109.5 .
H9A C9 H9C 109.5 .
H9B C9 H9C 109.5 .
C7 C10 H10A 109.5 .
C7 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
C7 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
C12 C11 S3 115.28(17) .
C12 C11 H11A 108.5 .
S3 C11 H11A 108.5 .
C12 C11 H11B 108.5 .
S3 C11 H11B 108.5 .
H11A C11 H11B 107.5 .
C11 C12 C13 112.14(19) .
C11 C12 H12A 109.2 .
C13 C12 H12A 109.2 .
C11 C12 H12B 109.2 .
C13 C12 H12B 109.2 .
H12A C12 H12B 107.9 .
C14 C13 C12 112.9(2) .
C14 C13 H13A 109.0 .
C12 C13 H13A 109.0 .
C14 C13 H13B 109.0 .
C12 C13 H13B 109.0 .
H13A C13 H13B 107.8 .
C13 C14 S6 114.40(16) .
C13 C14 H14A 108.7 .
S6 C14 H14A 108.7 .
C13 C14 H14B 108.7 .
S6 C14 H14B 108.7 .
H14A C14 H14B 107.6 .
C20 C15 C16 117.28(17) .
C20 C15 C2 123.72(16) .
C16 C15 C2 118.98(18) .
C15 C16 C17 120.7(2) .
C15 C16 H16 119.7 .
C17 C16 H16 119.7 .
C18 C17 C16 121.0(2) .
C18 C17 H17 119.5 .
C16 C17 H17 119.5 .
C19 C18 C17 120.1(2) .
C19 C18 H18 120.0 .
C17 C18 H18 120.0 .
C18 C19 C20 119.8(2) .
C18 C19 H19 120.1 .
C20 C19 H19 120.1 .
C15 C20 C19 121.03(19) .
C15 C20 C21 121.48(17) .
C19 C20 C21 117.3(2) .
N1 C21 C20 175.9(2) .
C27 C22 C23 117.57(17) .
C27 C22 C3 122.43(17) .
C23 C22 C3 119.95(16) .
C24 C23 C22 121.2(2) .
C24 C23 H23 119.4 .
C22 C23 H23 119.4 .
C23 C24 C25 120.5(2) .
C23 C24 H24 119.7 .
C25 C24 H24 119.7 .
C26 C25 C24 120.20(19) .
C26 C25 H25 119.9 .
C24 C25 H25 119.9 .
C25 C26 C27 119.68(19) .
C25 C26 H26 120.2 .
C27 C26 H26 120.2 .
C26 C27 C22 120.80(19) .
C26 C27 C28 119.09(17) .
C22 C27 C28 119.92(17) .
N2 C28 C27 176.9(3) .
C2AS C1AS HAS1 109.5 .
C2AS C1AS HAS2 109.5 .
HAS1 C1AS HAS2 109.5 .
C2AS C1AS HAS3 109.5 .
HAS1 C1AS HAS3 109.5 .
HAS2 C1AS HAS3 109.5 .
N1AS C2AS C1AS 174.9(7) .
C2BS N1BS N1BS 115.4(11) 3_765
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7560(18) .
S1 C5 1.7607(19) .
S2 C6 1.7565(18) .
S2 C1 1.7563(18) .
S3 C5 1.7567(18) .
S3 C11 1.811(3) .
S4 C4 1.756(2) .
S4 C7 1.759(2) .
S5 C4 1.7566(19) .
S5 C8 1.756(2) .
S6 C8 1.759(2) .
S6 C14 1.822(2) .
N1 C21 1.147(3) .
N2 C28 1.128(3) .
C1 C2 1.348(2) .
C2 C3 1.490(3) .
C2 C15 1.490(2) .
C3 C4 1.349(3) .
C3 C22 1.480(2) .
C5 C6 1.331(3) .
C6 C9 1.500(3) .
C7 C8 1.334(3) .
C7 C10 1.501(4) .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.522(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C13 1.518(3) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 C14 1.509(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C20 1.392(3) .
C15 C16 1.402(3) .
C16 C17 1.385(3) .
C16 H16 0.9300 .
C17 C18 1.364(4) .
C17 H17 0.9300 .
C18 C19 1.364(4) .
C18 H18 0.9300 .
C19 C20 1.409(3) .
C19 H19 0.9300 .
C20 C21 1.431(3) .
C22 C27 1.402(2) .
C22 C23 1.387(3) .
C23 C24 1.381(3) .
C23 H23 0.9300 .
C24 C25 1.369(4) .
C24 H24 0.9300 .
C25 C26 1.370(3) .
C25 H25 0.9300 .
C26 C27 1.398(3) .
C26 H26 0.9300 .
C27 C28 1.435(3) .
C1AS C2AS 1.568(10) .
C1AS HAS1 0.9600 .
C1AS HAS2 0.9600 .
C1AS HAS3 0.9600 .
C2AS N1AS 1.157(9) .
C2BS N1BS 1.116(9) .
N1BS N1BS 1.86(2) 3_765
