#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/43/2234367.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2234367
loop_
_publ_author_name
'Salmerón-Valverde, Amparo'
'Bernès, Sylvain'
_publ_section_title
;
 9-(Dicyanomethylidene)fluorene--tetrathiafulvalene (1/1)
;
_journal_coeditor_code           QM2055
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o932
_journal_paper_doi               10.1107/S1600536812008124
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C16 H8 N2, C6 H4 S4'
_chemical_formula_moiety         'C16 H8 N2, C6 H4 S4'
_chemical_formula_sum            'C22 H12 N2 S4'
_chemical_formula_weight         432.58
_chemical_melting_point          403
_chemical_name_common
;
9-(Dicyanomethylidene)fluorene; tetrathiafulvalene
;
_chemical_name_systematic
;
9-(Dicyanomethylidene)fluorene--2-(2H-1,3-dithiol-2-ylidene)-2H-1,3-dithiole
(1/1)
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                94.525(12)
_cell_angle_beta                 103.687(12)
_cell_angle_gamma                103.252(12)
_cell_formula_units_Z            2
_cell_length_a                   7.9919(11)
_cell_length_b                   9.3696(14)
_cell_length_c                   14.195(2)
_cell_measurement_pressure       101(2)
_cell_measurement_reflns_used    57
_cell_measurement_temperature    296.0(10)
_cell_measurement_theta_max      12.15
_cell_measurement_theta_min      3.98
_cell_volume                     995.2(3)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics
;
SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL-Plus (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.0(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5766
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        14
_diffrn_standards_interval_count 48
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_T_max  0.68822
_exptl_absorpt_correction_T_min  0.64976
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(XSCANS; Siemens, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.211
_refine_ls_extinction_coef       0.0125(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL-Plus (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.951
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0481
_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)+(0.0414P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                1541
_reflns_number_total             3493
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            qm2055.cif
_cod_data_source_block           I
_cod_original_cell_volume        995.3(2)
_cod_database_code               2234367
_cod_database_fobs_code          2234367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.0179(5) 0.9147(5) 0.3451(3) 0.0587(11) Uani d . 1 1
H H1A -0.0058 0.9988 0.3201 0.070 Uiso calc R 1 1
C C2 -0.0704(6) 0.7737(5) 0.2941(3) 0.0718(14) Uani d . 1 1
H H2A -0.1543 0.7635 0.2345 0.086 Uiso calc R 1 1
C C3 -0.0341(7) 0.6488(5) 0.3318(4) 0.0767(14) Uani d . 1 1
H H3A -0.0935 0.5557 0.2967 0.092 Uiso calc R 1 1
C C4 0.0888(6) 0.6601(5) 0.4206(4) 0.0694(13) Uani d . 1 1
H H4A 0.1116 0.5755 0.4452 0.083 Uiso calc R 1 1
C C4A 0.1776(5) 0.7992(5) 0.4723(3) 0.0538(11) Uani d . 1 1
C C4B 0.3151(5) 0.8434(5) 0.5651(3) 0.0521(11) Uani d . 1 1
C C5 0.3937(6) 0.7596(5) 0.6298(4) 0.0643(12) Uani d . 1 1
H H5A 0.3570 0.6567 0.6188 0.077 Uiso calc R 1 1
C C6 0.5283(6) 0.8334(6) 0.7112(4) 0.0721(14) Uani d . 1 1
H H6A 0.5844 0.7783 0.7541 0.087 Uiso calc R 1 1
C C7 0.5818(6) 0.9857(6) 0.7309(3) 0.0676(13) Uani d . 1 1
H H7A 0.6712 1.0319 0.7869 0.081 Uiso calc R 1 1
C C8 0.5017(5) 1.0703(5) 0.6668(3) 0.0589(11) Uani d . 1 1
H H8A 0.5372 1.1732 0.6799 0.071 Uiso calc R 1 1
C C8A 0.3686(5) 1.0006(5) 0.5833(3) 0.0495(10) Uani d . 1 1
C C9 0.2619(5) 1.0585(5) 0.5019(3) 0.0448(10) Uani d . 1 1
C C9A 0.1426(5) 0.9265(4) 0.4344(3) 0.0485(10) Uani d . 1 1
C C10 0.2732(5) 1.2023(5) 0.4915(3) 0.0489(10) Uani d . 1 1
C C11 0.1603(6) 1.2507(4) 0.4121(3) 0.0545(11) Uani d . 1 1
N N12 0.0739(5) 1.2952(4) 0.3509(3) 0.0719(11) Uani d . 1 1
C C13 0.3997(6) 1.3228(5) 0.5590(3) 0.0577(12) Uani d . 1 1
N N14 0.5000(5) 1.4216(4) 0.6109(3) 0.0782(12) Uani d . 1 1
S S15 0.28023(18) 0.60731(16) -0.03391(10) 0.0884(5) Uani d . 1 1
C C16 0.1970(7) 0.6242(6) 0.0666(4) 0.0943(17) Uani d . 1 1
H H16A 0.0993 0.6633 0.0638 0.113 Uiso calc R 1 1
C C17 0.2751(7) 0.5805(6) 0.1473(4) 0.0866(16) Uani d . 1 1
H H17A 0.2330 0.5867 0.2028 0.104 Uiso calc R 1 1
S S18 0.45887(18) 0.51072(15) 0.14801(9) 0.0832(5) Uani d . 1 1
C C19 0.4457(5) 0.5248(5) 0.0235(3) 0.0636(13) Uani d . 1 1
S S20 0.26100(15) 1.13111(14) 0.99343(9) 0.0784(4) Uani d . 1 1
C C21 0.3288(6) 1.0451(6) 0.9025(3) 0.0742(14) Uani d . 1 1
H H21A 0.4389 1.0845 0.8909 0.089 Uiso calc R 1 1
C C22 0.2207(6) 0.9222(5) 0.8498(3) 0.0693(13) Uani d . 1 1
H H22A 0.2525 0.8725 0.8001 0.083 Uiso calc R 1 1
S S23 0.01752(15) 0.85519(14) 0.87520(8) 0.0661(4) Uani d . 1 1
C C24 0.0573(5) 0.9972(4) 0.9734(3) 0.0517(11) Uani d . 1 1
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 -2
-2 0 2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle
C9A C1 C2 . 118.5(4)
C9A C1 H1A . 120.8
C2 C1 H1A . 120.8
C3 C2 C1 . 120.4(4)
C3 C2 H2A . 119.8
C1 C2 H2A . 119.8
C4 C3 C2 . 121.2(4)
C4 C3 H3A . 119.4
C2 C3 H3A . 119.4
C3 C4 C4A . 119.1(4)
C3 C4 H4A . 120.4
C4A C4 H4A . 120.4
C4 C4A C9A . 120.1(4)
C4 C4A C4B . 130.7(4)
C9A C4A C4B . 109.2(4)
C5 C4B C8A . 120.8(4)
C5 C4B C4A . 131.0(4)
C8A C4B C4A . 108.2(4)
C6 C5 C4B . 118.1(4)
C6 C5 H5A . 120.9
C4B C5 H5A . 120.9
C7 C6 C5 . 122.2(4)
C7 C6 H6A . 118.9
C5 C6 H6A . 118.9
C6 C7 C8 . 119.9(4)
C6 C7 H7A . 120.1
C8 C7 H7A . 120.1
C8A C8 C7 . 119.7(4)
C8A C8 H8A . 120.1
C7 C8 H8A . 120.1
C8 C8A C4B . 119.3(4)
C8 C8A C9 . 132.4(4)
C4B C8A C9 . 108.3(4)
C10 C9 C9A . 127.4(4)
C10 C9 C8A . 126.8(4)
C9A C9 C8A . 105.8(3)
C1 C9A C4A . 120.6(4)
C1 C9A C9 . 130.8(4)
C4A C9A C9 . 108.5(4)
C9 C10 C13 . 123.1(4)
C9 C10 C11 . 123.8(4)
C13 C10 C11 . 113.1(4)
N12 C11 C10 . 177.1(5)
N14 C13 C10 . 178.0(5)
C16 S15 C19 . 94.7(2)
C17 C16 S15 . 118.3(5)
C17 C16 H16A . 120.9
S15 C16 H16A . 120.9
C16 C17 S18 . 118.5(5)
C16 C17 H17A . 120.8
S18 C17 H17A . 120.8
C17 S18 C19 . 93.8(2)
C19 C19 S15 2_665 123.0(5)
C19 C19 S18 2_665 122.5(5)
S15 C19 S18 . 114.6(2)
C21 S20 C24 . 94.8(2)
C22 C21 S20 . 118.2(4)
C22 C21 H21A . 120.9
S20 C21 H21A . 120.9
C21 C22 S23 . 118.4(4)
C21 C22 H22A . 120.8
S23 C22 H22A . 120.8
C22 S23 C24 . 94.4(2)
C24 C24 S20 2_577 123.1(4)
C24 C24 S23 2_577 122.8(4)
S20 C24 S23 . 114.1(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C9A . 1.394(5)
C1 C2 . 1.395(5)
C1 H1A . 0.9300
C2 C3 . 1.386(6)
C2 H2A . 0.9300
C3 C4 . 1.382(6)
C3 H3A . 0.9300
C4 C4A . 1.386(5)
C4 H4A . 0.9300
C4A C9A . 1.404(5)
C4A C4B . 1.460(6)
C4B C5 . 1.386(5)
C4B C8A . 1.421(5)
C5 C6 . 1.384(6)
C5 H5A . 0.9300
C6 C7 . 1.378(6)
C6 H6A . 0.9300
C7 C8 . 1.392(5)
C7 H7A . 0.9300
C8 C8A . 1.388(5)
C8 H8A . 0.9300
C8A C9 . 1.483(5)
C9 C10 . 1.352(5)
C9 C9A . 1.482(5)
C10 C13 . 1.436(6)
C10 C11 . 1.442(6)
C11 N12 . 1.144(5)
C13 N14 . 1.147(5)
S15 C16 . 1.722(6)
S15 C19 . 1.752(4)
C16 C17 . 1.312(6)
C16 H16A . 0.9300
C17 S18 . 1.737(5)
C17 H17A . 0.9300
S18 C19 . 1.762(4)
C19 C19 2_665 1.351(8)
S20 C21 . 1.726(5)
S20 C24 . 1.759(4)
C21 C22 . 1.317(6)
C21 H21A . 0.9300
C22 S23 . 1.734(4)
C22 H22A . 0.9300
S23 C24 . 1.766(4)
C24 C24 2_577 1.324(7)
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_site_symmetry_4
_geom_torsion
C9A C1 C2 C3 . -0.1(6)
C1 C2 C3 C4 . 0.5(7)
C2 C3 C4 C4A . -0.3(7)
C3 C4 C4A C9A . -0.1(6)
C3 C4 C4A C4B . -178.2(4)
C4 C4A C4B C5 . -2.0(7)
C9A C4A C4B C5 . 179.7(4)
C4 C4A C4B C8A . 176.8(4)
C9A C4A C4B C8A . -1.4(4)
C8A C4B C5 C6 . -1.5(6)
C4A C4B C5 C6 . 177.3(4)
C4B C5 C6 C7 . 1.9(6)
C5 C6 C7 C8 . -1.1(6)
C6 C7 C8 C8A . -0.2(6)
C7 C8 C8A C4B . 0.6(5)
C7 C8 C8A C9 . -179.0(4)
C5 C4B C8A C8 . 0.3(5)
C4A C4B C8A C8 . -178.7(3)
C5 C4B C8A C9 . 179.9(3)
C4A C4B C8A C9 . 0.9(4)
C8 C8A C9 C10 . 0.1(6)
C4B C8A C9 C10 . -179.5(4)
C8 C8A C9 C9A . 179.4(4)
C4B C8A C9 C9A . -0.2(4)
C2 C1 C9A C4A . -0.3(6)
C2 C1 C9A C9 . 176.7(4)
C4 C4A C9A C1 . 0.4(6)
C4B C4A C9A C1 . 178.9(3)
C4 C4A C9A C9 . -177.2(4)
C4B C4A C9A C9 . 1.3(4)
C10 C9 C9A C1 . 1.4(6)
C8A C9 C9A C1 . -178.0(4)
C10 C9 C9A C4A . 178.7(4)
C8A C9 C9A C4A . -0.7(4)
C9A C9 C10 C13 . -176.9(4)
C8A C9 C10 C13 . 2.3(6)
C9A C9 C10 C11 . 3.1(6)
C8A C9 C10 C11 . -177.6(3)
C19 S15 C16 C17 . 1.9(5)
S15 C16 C17 S18 . 0.8(6)
C16 C17 S18 C19 . -3.0(5)
C16 S15 C19 C19 2_665 175.8(5)
C16 S15 C19 S18 . -3.9(3)
C17 S18 C19 C19 2_665 -175.6(5)
C17 S18 C19 S15 . 4.2(3)
C24 S20 C21 C22 . 1.5(4)
S20 C21 C22 S23 . 0.1(6)
C21 C22 S23 C24 . -1.5(4)
C21 S20 C24 C24 2_577 178.3(5)
C21 S20 C24 S23 . -2.4(3)
C22 S23 C24 C24 2_577 -178.3(5)
C22 S23 C24 S20 . 2.4(3)
