#------------------------------------------------------------------------------
#$Date: 2019-09-19 11:42:06 +0300 (Thu, 19 Sep 2019) $
#$Revision: 218530 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/39/7233947.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_7233947
loop_
_publ_author_name
'Mikkel A. Christensen'
'Christian R. Parker'
'Thomas Just Sorensen'
'Sebastian de Graaf'
'Thorbjorn J. Morsing'
'Theis Brock-Nannestad'
'Jesper Bendix'
'Michael M. Haley'
'Peter Rapta'
'Andrey Danilov'
'Sergey Kubatkin'
'Ole Hammerich'
'Mogens Brondsted Nielsen'
_publ_section_title
;
 Mixed valence radical cations and intermolecular complexes derived from
 indenofluorene-extended tetrathiafulvalenes
;
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              10428
_journal_page_last               10438
_journal_paper_doi               10.1039/C4TC02178A
_journal_volume                  2
_journal_year                    2014
_chemical_formula_sum            'C42 H46 S8'
_chemical_formula_weight         807.35
_chemical_name_systematic
;
 2-{11-[4,5-bis(butylsulfanyl)-1,3-dithiolan-2-
ylidene]-5H,11H-indeno[1,2-b]fluoren-5-ylidene}-
4,5-bis(butylsulfanyl)-1,3-dithiolane
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                103.453(9)
_cell_angle_beta                 106.211(12)
_cell_angle_gamma                94.229(10)
_cell_formula_units_Z            1
_cell_length_a                   8.4030(6)
_cell_length_b                   9.0350(11)
_cell_length_c                   14.0030(13)
_cell_measurement_reflns_used    30687
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      1.00
_cell_volume                     981.83(19)
_computing_cell_refinement       'COLLECT (Nonius, 1999)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'EvalCCD (Duisenberg et al.,  2003)'
_computing_molecular_graphics    'Mercury 3.0 (2011)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius KappaCCD area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0508
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30687
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.482
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
Gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.449
_exptl_crystal_size_mid          0.315
_exptl_crystal_size_min          0.082
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0300
_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)+(0.0000P)²+0.4732P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0749
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                4968
_reflns_number_total             5715
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1000001.cif
_cod_data_source_block           PCOD1000001
_cod_original_cell_volume        981.83(17)
_cod_database_code               7233947
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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.16619(4) 0.24480(4) 0.22885(2) 0.02044(7) Uani 1 1 d . . .
S2 S 0.26501(4) -0.01186(3) 0.09989(2) 0.02085(7) Uani 1 1 d . . .
S3 S 0.37465(5) -0.16494(4) 0.27429(3) 0.02737(8) Uani 1 1 d . . .
S4 S 0.26617(4) 0.12868(4) 0.41749(2) 0.02506(8) Uani 1 1 d . . .
C5 C 0.06763(14) 0.37042(13) 0.02518(9) 0.0163(2) Uani 1 1 d . . .
C6 C 0.29337(15) -0.01463(14) 0.22763(9) 0.0195(2) Uani 1 1 d . . .
C7 C 0.18418(14) 0.16304(13) 0.10725(9) 0.0175(2) Uani 1 1 d . . .
C8 C 0.24877(15) 0.10460(14) 0.28743(9) 0.0201(2) Uani 1 1 d . . .
C9 C 0.09024(14) 0.26661(13) -0.13873(9) 0.0173(2) Uani 1 1 d . . .
C10 C 0.03900(14) 0.39484(13) -0.07485(9) 0.0165(2) Uani 1 1 d . . .
C11 C 0.20781(17) 0.00795(15) -0.22554(10) 0.0251(3) Uani 1 1 d . . .
H11 H 0.2515 -0.0740 -0.2527 0.030 Uiso 1 1 d R . .
C12 C 0.14395(17) 0.10592(15) -0.28489(10) 0.0238(3) Uani 1 1 d . . .
H12 H 0.1527 0.0793 -0.3543 0.029 Uiso 1 1 d R . .
C13 C 0.02663(15) 0.47818(14) 0.10039(9) 0.0182(2) Uani 1 1 d . . .
H13 H 0.0458 0.4722 0.1658 0.022 Uiso 1 1 d R . .
C14 C 0.15270(15) 0.16642(14) -0.07817(9) 0.0176(2) Uani 1 1 d . . .
C15 C 0.21292(17) 0.03605(15) -0.12270(10) 0.0231(2) Uani 1 1 d . . .
H15 H 0.2501 -0.0319 -0.0861 0.028 Uiso 1 1 d R . .
C16 C 0.13942(14) 0.22715(13) 0.02577(9) 0.0171(2) Uani 1 1 d . . .
C17 C 0.08537(16) 0.23704(15) -0.24135(9) 0.0212(2) Uani 1 1 d . . .
H17 H 0.0396 0.3027 -0.2782 0.025 Uiso 1 1 d R . .
C18 C 0.42321(16) -0.28895(15) 0.16754(10) 0.0225(2) Uani 1 1 d . . .
H18A H 0.5072 -0.2252 0.1447 0.027 Uiso 1 1 d R . .
H18B H 0.3279 -0.3241 0.1125 0.027 Uiso 1 1 d R . .
C19 C 0.49724(17) -0.41909(15) 0.20823(11) 0.0258(3) Uani 1 1 d . . .
H19A H 0.4188 -0.4774 0.2293 0.031 Uiso 1 1 d R . .
H19B H 0.5870 -0.3783 0.2671 0.031 Uiso 1 1 d R . .
C20 C 0.61073(18) 0.22441(17) 0.46109(11) 0.0276(3) Uani 1 1 d . . .
H20A H 0.6356 0.1356 0.4846 0.033 Uiso 1 1 d R . .
H20B H 0.6063 0.1979 0.3945 0.033 Uiso 1 1 d R . .
C21 C 0.45060(17) 0.27593(16) 0.47628(10) 0.0268(3) Uani 1 1 d . . .
H21A H 0.4479 0.2953 0.5473 0.032 Uiso 1 1 d R . .
H21B H 0.4196 0.3617 0.4482 0.032 Uiso 1 1 d R . .
C22 C 0.9219(2) 0.2979(2) 0.49836(14) 0.0387(4) Uani 1 1 d . . .
C23 C 0.76154(19) 0.34888(19) 0.51546(12) 0.0345(3) Uani 1 1 d . . .
H23A H 0.7430 0.4380 0.4979 0.041 Uiso 1 1 d R . .
H23B H 0.7652 0.3770 0.5870 0.041 Uiso 1 1 d R . .
C24 C 0.54892(19) -0.53416(17) 0.12912(13) 0.0335(3) Uani 1 1 d . . .
H24A H 0.6212 -0.4771 0.1031 0.040 Uiso 1 1 d R . .
H24B H 0.4465 -0.5850 0.0756 0.040 Uiso 1 1 d R . .
C25 C 0.6355(3) -0.6552(2) 0.1742(2) 0.0573(6) Uani 1 1 d . . .
H25A H 0.666(3) -0.721(3) 0.1245(19) 0.070(7) Uiso 1 1 d . . .
H25B H 0.562(3) -0.714(3) 0.1942(19) 0.068(7) Uiso 1 1 d . . .
H25C H 0.736(3) -0.607(3) 0.2322(18) 0.063(7) Uiso 1 1 d . . .
H22A H 1.019(3) 0.376(3) 0.5379(17) 0.054(6) Uiso 1 1 d . . .
H22B H 0.920(3) 0.283(2) 0.4269(16) 0.049(6) Uiso 1 1 d . . .
H22C H 0.936(3) 0.202(3) 0.5171(16) 0.050(6) Uiso 1 1 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'
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
C7 S1 C8 96.96(6) . .
C6 S2 C7 96.95(6) . .
C6 S3 C18 105.22(6) . .
C8 S4 C21 99.94(6) . .
C13 C5 C10 118.68(10) . .
C13 C5 C16 132.92(11) . .
C10 C5 C16 108.40(10) . .
C8 C6 S3 122.26(10) . .
C8 C6 S2 116.53(9) . .
S3 C6 S2 121.21(7) . .
C16 C7 S1 123.91(9) . .
C16 C7 S2 123.39(9) . .
S1 C7 S2 112.71(7) . .
C6 C8 S4 125.20(10) . .
C6 C8 S1 116.83(10) . .
S4 C8 S1 117.97(7) . .
C17 C9 C14 121.40(11) . .
C17 C9 C10 129.97(11) . .
C14 C9 C10 108.64(10) . .
C13 C10 C5 122.73(10) 2_565 .
C13 C10 C9 129.28(11) 2_565 .
C5 C10 C9 107.98(10) . .
C12 C11 C15 121.55(12) . .
C12 C11 H11 120.0 . .
C15 C11 H11 118.4 . .
C11 C12 C17 120.03(12) . .
C11 C12 H12 114.8 . .
C17 C12 H12 125.0 . .
C10 C13 C5 118.59(10) 2_565 .
C10 C13 H13 118.0 2_565 .
C5 C13 H13 123.3 . .
C15 C14 C9 118.95(11) . .
C15 C14 C16 132.46(11) . .
C9 C14 C16 108.60(10) . .
C11 C15 C14 119.09(12) . .
C11 C15 H15 120.2 . .
C14 C15 H15 120.6 . .
C7 C16 C5 126.57(11) . .
C7 C16 C14 127.06(10) . .
C5 C16 C14 106.37(10) . .
C9 C17 C12 118.98(12) . .
C9 C17 H17 118.2 . .
C12 C17 H17 122.7 . .
C19 C18 S3 105.57(9) . .
C19 C18 H18A 112.5 . .
S3 C18 H18A 108.8 . .
C19 C18 H18B 112.2 . .
S3 C18 H18B 109.9 . .
H18A C18 H18B 107.8 . .
C24 C19 C18 113.10(12) . .
C24 C19 H19A 106.0 . .
C18 C19 H19A 111.9 . .
C24 C19 H19B 110.7 . .
C18 C19 H19B 109.4 . .
H19A C19 H19B 105.4 . .
C21 C20 C23 112.57(12) . .
C21 C20 H20A 112.8 . .
C23 C20 H20A 107.5 . .
C21 C20 H20B 112.5 . .
C23 C20 H20B 106.1 . .
H20A C20 H20B 104.9 . .
C20 C21 S4 114.70(10) . .
C20 C21 H21A 114.0 . .
S4 C21 H21A 97.5 . .
C20 C21 H21B 113.6 . .
S4 C21 H21B 104.6 . .
H21A C21 H21B 111.0 . .
C23 C22 H22A 111.5(13) . .
C23 C22 H22B 112.0(12) . .
H22A C22 H22B 104.8(17) . .
C23 C22 H22C 109.1(12) . .
H22A C22 H22C 110.5(17) . .
H22B C22 H22C 108.9(17) . .
C20 C23 C22 112.48(13) . .
C20 C23 H23A 111.3 . .
C22 C23 H23A 111.5 . .
C20 C23 H23B 105.6 . .
C22 C23 H23B 113.8 . .
H23A C23 H23B 101.4 . .
C19 C24 C25 112.04(16) . .
C19 C24 H24A 107.4 . .
C25 C24 H24A 111.3 . .
C19 C24 H24B 106.1 . .
C25 C24 H24B 108.3 . .
H24A C24 H24B 111.6 . .
C24 C25 H25A 109.2(16) . .
C24 C25 H25B 110.5(15) . .
H25A C25 H25B 106(2) . .
C24 C25 H25C 110.5(14) . .
H25A C25 H25C 109(2) . .
H25B C25 H25C 111(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C7 1.7444(12) .
S1 C8 1.7476(12) .
S2 C6 1.7438(13) .
S2 C7 1.7580(12) .
S3 C6 1.7431(12) .
S3 C18 1.8125(13) .
S4 C8 1.7458(13) .
S4 C21 1.8230(15) .
C5 C13 1.3967(16) .
C5 C10 1.4255(16) .
C5 C16 1.4686(16) .
C6 C8 1.3480(17) .
C7 C16 1.3708(16) .
C9 C17 1.3874(16) .
C9 C14 1.4117(16) .
C9 C10 1.4609(15) .
C10 C13 1.3865(16) 2_565
C11 C12 1.3876(19) .
C11 C15 1.3907(18) .
C11 H11 0.9025 .
C12 C17 1.3911(17) .
C12 H12 0.9707 .
C13 C10 1.3865(16) 2_565
C13 H13 0.9000 .
C14 C15 1.3981(16) .
C14 C16 1.4697(16) .
C15 H15 0.9066 .
C17 H17 0.9118 .
C18 C19 1.5218(18) .
C18 H18A 1.0408 .
C18 H18B 0.9164 .
C19 C24 1.5153(19) .
C19 H19A 0.9634 .
C19 H19B 0.9240 .
C20 C21 1.5095(18) .
C20 C23 1.518(2) .
C20 H20A 0.9512 .
C20 H20B 0.8959 .
C21 H21A 0.9761 .
C21 H21B 0.9681 .
C22 C23 1.518(2) .
C22 H22A 0.97(2) .
C22 H22B 0.97(2) .
C22 H22C 0.96(2) .
C23 H23A 0.9074 .
C23 H23B 0.9649 .
C24 C25 1.518(3) .
C24 H24A 0.9651 .
C24 H24B 0.9667 .
C25 H25A 0.91(3) .
C25 H25B 0.93(3) .
C25 H25C 0.98(2) .
