#------------------------------------------------------------------------------
#$Date: 2015-05-29 10:45:52 +0300 (Fri, 29 May 2015) $
#$Revision: 137528 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/05/7220584.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_7220584
loop_
_publ_author_name
'Christensen, Mikkel A.'
'Rudebusch, Gabriel E.'
'Parker, Christian Richard'
'Andersen, Cecilie Lindholm'
'Kadziola, Anders'
'Haley, Michael M.'
'Hammerich, Ole'
'Nielsen, Mogens Brondsted'
_publ_section_title
;
 Diindenothienoacene--tetrathiafulvalene redox systems
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA09581F
_journal_year                    2015
_chemical_formula_sum            'C21 H22 S5'
_chemical_formula_weight         434.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-03-26 deposited with the CCDC.
2015-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                106.867(3)
_cell_angle_beta                 104.772(3)
_cell_angle_gamma                97.842(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4813(6)
_cell_length_b                   9.5976(7)
_cell_length_c                   14.0855(10)
_cell_measurement_reflns_used    18356
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      30.55
_cell_measurement_theta_min      2.28
_cell_volume                     1033.18(13)
_computing_cell_refinement       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_collection       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_reduction        'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'APEX2 v.2013.6-2, Bruker/Nonius'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.665
_diffrn_measured_fraction_theta_max 0.665
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.0486
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18356
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.680
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_refine_diff_density_max         0.466
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     408
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0463
_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)+(0.1013P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1539
_reflns_number_gt                3347
_reflns_number_total             4204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra09581f2.cif
_cod_data_source_block           mo_d8v831_0m
_cod_database_code               7220584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
S1 S -0.13824(9) 0.69962(8) 0.07506(6) 0.02307(17) Uani 1 1 d U
S2 S -0.03470(8) 0.98029(8) 0.26181(5) 0.01911(16) Uani 1 1 d U
S3 S -0.08040(7) 1.31028(7) 0.36404(5) 0.01615(16) Uani 1 1 d U
S4 S 0.18392(8) 0.85709(8) 0.39625(5) 0.01822(16) Uani 1 1 d U
S5 S 0.10612(9) 0.55665(8) 0.22388(6) 0.02473(18) Uani 1 1 d U
C1 C 0.4196(5) 0.7934(5) -0.0303(3) 0.0433(8) Uani 1 1 d U
H1A H 0.4886 0.8441 0.0426 0.065 Uiso 1 1 calc R
H1B H 0.4697 0.8323 -0.0756 0.065 Uiso 1 1 calc R
H1C H 0.4134 0.6857 -0.0490 0.065 Uiso 1 1 calc R
C2 C 0.2435(4) 0.8215(4) -0.0442(3) 0.0349(6) Uani 1 1 d U
H2A H 0.2508 0.9306 -0.0231 0.042 Uiso 1 1 calc R
H2B H 0.1768 0.7763 -0.1189 0.042 Uiso 1 1 calc R
C3 C 0.1543(4) 0.7565(4) 0.0202(2) 0.0271(5) Uani 1 1 d U
H3A H 0.1454 0.6472 -0.0017 0.032 Uiso 1 1 calc R
H3B H 0.2221 0.8004 0.0948 0.032 Uiso 1 1 calc R
C4 C -0.0192(4) 0.7865(4) 0.0081(2) 0.0253(5) Uani 1 1 d U
H4A H -0.0831 0.7500 -0.0672 0.030 Uiso 1 1 calc R
H4B H -0.0087 0.8959 0.0348 0.030 Uiso 1 1 calc R
C5 C -0.0174(3) 0.7981(3) 0.2051(2) 0.0192(4) Uani 1 1 d U
C6 C 0.1002(3) 1.0108(3) 0.3853(2) 0.0167(4) Uani 1 1 d U
C7 C 0.1342(3) 1.1430(3) 0.4649(2) 0.0165(4) Uani 1 1 d U
C8 C 0.0630(3) 1.2711(3) 0.4595(2) 0.0162(4) Uani 1 1 d U
C9 C 0.1243(3) 1.3867(3) 0.5535(2) 0.0162(4) Uani 1 1 d U
C10 C 0.0574(3) 1.5126(3) 0.5494(2) 0.0161(4) Uani 1 1 d U
C11 C 0.0825(3) 0.7397(3) 0.2672(2) 0.0183(4) Uani 1 1 d U
C12 C 0.2403(3) 1.3390(3) 0.6273(2) 0.0167(4) Uani 1 1 d U
C13 C 0.3325(3) 1.4114(3) 0.7317(2) 0.0192(4) Uani 1 1 d U
H13 H 0.3263 1.5099 0.7676 0.023 Uiso 1 1 calc R
C14 C 0.4349(3) 1.3351(3) 0.7825(2) 0.0211(4) Uani 1 1 d U
H14 H 0.4979 1.3818 0.8541 0.025 Uiso 1 1 calc R
C15 C 0.4454(3) 1.1916(3) 0.7291(2) 0.0214(5) Uani 1 1 d U
H15 H 0.5176 1.1428 0.7646 0.026 Uiso 1 1 calc R
C16 C 0.3521(3) 1.1181(3) 0.6245(2) 0.0205(4) Uani 1 1 d U
H16 H 0.3596 1.0199 0.5889 0.025 Uiso 1 1 calc R
C17 C 0.2477(3) 1.1914(3) 0.5732(2) 0.0169(4) Uani 1 1 d U
C18 C 0.2688(3) 0.5410(3) 0.3307(2) 0.0196(4) Uani 1 1 d U
H18A H 0.3713 0.6200 0.3509 0.024 Uiso 1 1 calc R
H18B H 0.2300 0.5502 0.3924 0.024 Uiso 1 1 calc R
C19 C 0.3029(3) 0.3866(3) 0.2889(2) 0.0214(5) Uani 1 1 d U
H19A H 0.3466 0.3820 0.2295 0.026 Uiso 1 1 calc R
H19B H 0.1962 0.3106 0.2624 0.026 Uiso 1 1 calc R
C20 C 0.4286(4) 0.3487(4) 0.3716(2) 0.0248(5) Uani 1 1 d U
H20A H 0.5357 0.4242 0.3981 0.030 Uiso 1 1 calc R
H20B H 0.3851 0.3524 0.4310 0.030 Uiso 1 1 calc R
C21 C 0.4598(4) 0.1936(4) 0.3270(3) 0.0380(8) Uani 1 1 d U
H21A H 0.3538 0.1188 0.3004 0.057 Uiso 1 1 calc R
H21B H 0.5387 0.1717 0.3819 0.057 Uiso 1 1 calc R
H21C H 0.5069 0.1909 0.2699 0.057 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C5 S1 C4 100.15(14) . .
C6 S2 C5 96.60(12) . .
C10 S3 C8 90.20(12) 2_586 .
C11 S4 C6 96.43(12) . .
C11 S5 C18 105.25(13) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C1 112.3(3) . .
C3 C2 H2A 109.1 . .
C1 C2 H2A 109.1 . .
C3 C2 H2B 109.1 . .
C1 C2 H2B 109.1 . .
H2A C2 H2B 107.9 . .
C4 C3 C2 112.4(2) . .
C4 C3 H3A 109.1 . .
C2 C3 H3A 109.1 . .
C4 C3 H3B 109.1 . .
C2 C3 H3B 109.1 . .
H3A C3 H3B 107.8 . .
C3 C4 S1 114.55(18) . .
C3 C4 H4A 108.6 . .
S1 C4 H4A 108.6 . .
C3 C4 H4B 108.6 . .
S1 C4 H4B 108.6 . .
H4A C4 H4B 107.6 . .
C11 C5 S2 117.0(2) . .
C11 C5 S1 124.5(2) . .
S2 C5 S1 118.38(13) . .
C7 C6 S2 121.88(17) . .
C7 C6 S4 124.43(18) . .
S2 C6 S4 113.69(16) . .
C6 C7 C8 125.9(2) . .
C6 C7 C17 129.9(2) . .
C8 C7 C17 104.3(2) . .
C9 C8 C7 111.0(2) . .
C9 C8 S3 113.70(18) . .
C7 C8 S3 135.2(2) . .
C8 C9 C10 111.9(2) . .
C8 C9 C12 108.4(2) . .
C10 C9 C12 139.8(3) . .
C10 C10 C9 112.1(3) 2_586 .
C10 C10 S3 112.2(2) 2_586 2_586
C9 C10 S3 135.8(2) . 2_586
C5 C11 S5 122.6(2) . .
C5 C11 S4 116.2(2) . .
S5 C11 S4 121.10(13) . .
C13 C12 C17 121.3(2) . .
C13 C12 C9 131.5(2) . .
C17 C12 C9 107.2(2) . .
C12 C13 C14 118.1(3) . .
C12 C13 H13 120.9 . .
C14 C13 H13 120.9 . .
C15 C14 C13 120.7(3) . .
C15 C14 H14 119.6 . .
C13 C14 H14 119.6 . .
C14 C15 C16 121.3(2) . .
C14 C15 H15 119.4 . .
C16 C15 H15 119.4 . .
C17 C16 C15 118.8(3) . .
C17 C16 H16 120.6 . .
C15 C16 H16 120.6 . .
C16 C17 C12 119.7(2) . .
C16 C17 C7 131.2(3) . .
C12 C17 C7 109.1(2) . .
C19 C18 S5 105.42(19) . .
C19 C18 H18A 110.7 . .
S5 C18 H18A 110.7 . .
C19 C18 H18B 110.7 . .
S5 C18 H18B 110.7 . .
H18A C18 H18B 108.8 . .
C18 C19 C20 112.8(3) . .
C18 C19 H19A 109.0 . .
C20 C19 H19A 109.0 . .
C18 C19 H19B 109.0 . .
C20 C19 H19B 109.0 . .
H19A C19 H19B 107.8 . .
C21 C20 C19 111.3(3) . .
C21 C20 H20A 109.4 . .
C19 C20 H20A 109.4 . .
C21 C20 H20B 109.4 . .
C19 C20 H20B 109.4 . .
H20A C20 H20B 108.0 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C5 1.753(3) .
S1 C4 1.821(3) .
S2 C6 1.738(3) .
S2 C5 1.742(3) .
S3 C10 1.732(3) 2_586
S3 C8 1.736(2) .
S4 C11 1.750(3) .
S4 C6 1.751(2) .
S5 C11 1.742(3) .
S5 C18 1.822(2) .
C1 C2 1.527(5) .
C1 H1A 0.9800 .
C1 H1B 0.9800 .
C1 H1C 0.9800 .
C2 C3 1.529(4) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.514(4) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C11 1.355(3) .
C6 C7 1.364(4) .
C7 C8 1.455(3) .
C7 C17 1.478(4) .
C8 C9 1.376(4) .
C9 C10 1.413(3) .
C9 C12 1.461(3) .
C10 C10 1.412(5) 2_586
C10 S3 1.732(3) 2_586
C12 C13 1.389(4) .
C12 C17 1.419(4) .
C13 C14 1.401(3) .
C13 H13 0.9500 .
C14 C15 1.392(4) .
C14 H14 0.9500 .
C15 C16 1.394(4) .
C15 H15 0.9500 .
C16 C17 1.393(3) .
C16 H16 0.9500 .
C18 C19 1.524(4) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C19 C20 1.531(3) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 C21 1.526(4) .
C20 H20A 0.9900 .
C20 H20B 0.9900 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
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
C1 C2 C3 C4 179.0(3) . .
C2 C3 C4 S1 175.6(2) . .
C5 S1 C4 C3 65.9(3) . .
C6 S2 C5 C11 0.9(2) . .
C6 S2 C5 S1 177.34(17) . .
C4 S1 C5 C11 -107.4(3) . .
C4 S1 C5 S2 76.50(18) . .
C5 S2 C6 C7 180.0(2) . .
C5 S2 C6 S4 -0.49(17) . .
C11 S4 C6 C7 179.6(2) . .
C11 S4 C6 S2 0.07(17) . .
S2 C6 C7 C8 1.5(4) . .
S4 C6 C7 C8 -178.0(2) . .
S2 C6 C7 C17 -178.0(2) . .
S4 C6 C7 C17 2.5(4) . .
C6 C7 C8 C9 -179.7(3) . .
C17 C7 C8 C9 -0.1(3) . .
C6 C7 C8 S3 1.2(4) . .
C17 C7 C8 S3 -179.2(2) . .
C10 S3 C8 C9 0.8(2) 2_586 .
C10 S3 C8 C7 179.8(3) 2_586 .
C7 C8 C9 C10 179.6(2) . .
S3 C8 C9 C10 -1.1(3) . .
C7 C8 C9 C12 -0.5(3) . .
S3 C8 C9 C12 178.84(16) . .
C8 C9 C10 C10 0.9(4) . 2_586
C12 C9 C10 C10 -179.0(3) . 2_586
C8 C9 C10 S3 -179.5(2) . 2_586
C12 C9 C10 S3 0.5(5) . 2_586
S2 C5 C11 S5 177.25(15) . .
S1 C5 C11 S5 1.1(4) . .
S2 C5 C11 S4 -1.0(3) . .
S1 C5 C11 S4 -177.20(16) . .
C18 S5 C11 C5 173.8(2) . .
C18 S5 C11 S4 -8.0(2) . .
C6 S4 C11 C5 0.6(2) . .
C6 S4 C11 S5 -177.73(17) . .
C8 C9 C12 C13 -178.7(3) . .
C10 C9 C12 C13 1.2(5) . .
C8 C9 C12 C17 0.9(3) . .
C10 C9 C12 C17 -179.2(3) . .
C17 C12 C13 C14 0.5(4) . .
C9 C12 C13 C14 -179.9(3) . .
C12 C13 C14 C15 0.9(4) . .
C13 C14 C15 C16 -1.4(4) . .
C14 C15 C16 C17 0.5(4) . .
C15 C16 C17 C12 1.0(4) . .
C15 C16 C17 C7 -179.3(3) . .
C13 C12 C17 C16 -1.5(4) . .
C9 C12 C17 C16 178.8(2) . .
C13 C12 C17 C7 178.7(2) . .
C9 C12 C17 C7 -1.0(3) . .
C6 C7 C17 C16 0.5(5) . .
C8 C7 C17 C16 -179.1(3) . .
C6 C7 C17 C12 -179.7(3) . .
C8 C7 C17 C12 0.7(3) . .
C11 S5 C18 C19 -174.18(18) . .
S5 C18 C19 C20 -175.71(19) . .
C18 C19 C20 C21 -179.9(3) . .
