#------------------------------------------------------------------------------
#$Date: 2019-03-05 09:52:05 +0100 (mar 05 de mar de 2019) $
#$Revision: 213973 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/11/7051183.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_7051183
loop_
_publ_author_name
'Thomas Devic'
'Josep N. Bertran'
'Benoît Domercq'
'Enric Canadell'
'Narcis Avarvari'
'Pascale Auban-Senzier'
'Marc Fourmigué'
_publ_section_title
;
 Cation radical salts of cyano(ethylenedithio)tetrathiafulvalene with
 halogenated anions: annihilation of the CN···Hal
 interaction and stabilisation of conducting, antiferromagnetic square
 or chain-type salts
;
_journal_issue                   11
_journal_name_full               'New J. Chem.'
_journal_page_first              1418
_journal_page_last               1424
_journal_paper_doi               10.1039/b104640n
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C9 H5 N S6'
_chemical_formula_weight         319.50
_chemical_name_common            (CN)EDT-TTF
_chemical_name_systematic
; 
4-cyano-4',5'-ethylendithio-tetrathiafulvalene 
;
_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           SHELXL-97
_cell_angle_alpha                104.45(3)
_cell_angle_beta                 93.03(3)
_cell_angle_gamma                95.46(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9395(14)
_cell_length_b                   7.6083(15)
_cell_length_c                   12.502(3)
_cell_measurement_reflns_used    3585
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.85
_cell_measurement_theta_min      2.8
_cell_volume                     634.3(3)
_computing_cell_refinement       'SELECT, Stoe-IPDS'
_computing_data_collection       'EXPOSE, Stoe-IPDS'
_computing_data_reduction        'INTEGRATE, Stoe IPDS'
_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 0.873
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_device_type  'Stoe IPDS'
_diffrn_measurement_method       'rotation, phi incr. 1.9 deg'
_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  0.0582
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5854
_diffrn_reflns_theta_full        25.95
_diffrn_reflns_theta_max         25.95
_diffrn_reflns_theta_min         2.78
_exptl_absorpt_coefficient_mu    1.046
_exptl_absorpt_correction_T_max  0.9533
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'FACEIT, Stoe-IPDS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.038
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.274
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2170
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.274
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0559
_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)+(0.0000P)²+2.3951P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1283
_refine_ls_wR_factor_ref         0.1340
_reflns_number_gt                1501
_reflns_number_total             2170
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b104640n.txt
_cod_data_source_block           edtcn
_cod_original_cell_volume        634.3(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7051183
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 0.1048(2) 0.7079(2) -0.03905(13) 0.0362(4) Uani 1 1 d . . .
S2 S -0.3474(2) 0.6482(3) -0.09296(14) 0.0399(5) Uani 1 1 d . . .
S3 S 0.0384(2) 0.9589(2) 0.20370(14) 0.0380(5) Uani 1 1 d . . .
S4 S -0.4117(2) 0.9063(3) 0.14824(14) 0.0418(5) Uani 1 1 d . . .
S5 S 0.0147(3) 1.2241(3) 0.42181(15) 0.0473(5) Uani 1 1 d . . .
S6 S -0.5103(3) 1.1600(3) 0.35123(16) 0.0572(6) Uani 1 1 d . . .
N1 N 0.2701(10) 0.4175(9) -0.2977(5) 0.0578(18) Uani 1 1 d . . .
C1 C 0.1517(10) 0.4819(10) -0.2405(6) 0.0426(17) Uani 1 1 d . . .
C2 C 0.0069(10) 0.5631(8) -0.1670(5) 0.0343(15) Uani 1 1 d . . .
C3 C -0.1960(10) 0.5380(10) -0.1896(5) 0.0410(17) Uani 1 1 d . . .
H3 H -0.2504 0.4619 -0.2568 0.049 Uiso 1 1 calc R . .
C4 C -0.1408(9) 0.7527(8) 0.0042(5) 0.0315(15) Uani 1 1 d . . .
C5 C -0.1681(9) 0.8593(9) 0.1047(5) 0.0337(15) Uani 1 1 d . . .
C6 C -0.1144(9) 1.0866(9) 0.2995(5) 0.0330(15) Uani 1 1 d . . .
C7 C -0.3176(9) 1.0625(9) 0.2744(5) 0.0339(15) Uani 1 1 d . . .
C8 C -0.1875(12) 1.2145(15) 0.5125(6) 0.073(3) Uani 1 1 d . . .
H8A H -0.2135 1.0892 0.5172 0.087 Uiso 1 1 calc R . .
H8B H -0.1420 1.2878 0.5863 0.087 Uiso 1 1 calc R . .
C9 C -0.3775(12) 1.2762(15) 0.4810(7) 0.075(3) Uani 1 1 d . . .
H9A H -0.3524 1.4041 0.4816 0.090 Uiso 1 1 calc R . .
H9B H -0.4626 1.2696 0.5393 0.090 Uiso 1 1 calc R . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0302(9) 0.0418(10) 0.0302(9) -0.0036(7) 0.0025(7) 0.0059(8)
S2 0.0299(9) 0.0515(11) 0.0293(9) -0.0068(8) -0.0013(7) 0.0069(8)
S3 0.0271(9) 0.0456(10) 0.0314(9) -0.0095(8) 0.0011(7) 0.0076(8)
S4 0.0276(9) 0.0525(11) 0.0332(9) -0.0112(8) -0.0003(8) 0.0058(8)
S5 0.0318(10) 0.0638(12) 0.0309(9) -0.0139(9) 0.0033(8) -0.0015(9)
S6 0.0290(10) 0.0937(16) 0.0341(10) -0.0147(10) 0.0037(8) 0.0162(10)
N1 0.058(4) 0.069(4) 0.042(4) -0.001(3) 0.019(3) 0.020(4)
C1 0.038(4) 0.050(4) 0.035(4) 0.002(3) 0.003(3) 0.008(4)
C2 0.044(4) 0.027(3) 0.028(3) 0.000(3) 0.003(3) 0.007(3)
C3 0.045(4) 0.046(4) 0.023(3) -0.007(3) -0.002(3) 0.008(4)
C4 0.032(4) 0.029(3) 0.030(3) -0.001(3) 0.003(3) 0.004(3)
C5 0.032(4) 0.037(4) 0.029(3) 0.001(3) -0.001(3) 0.007(3)
C6 0.032(4) 0.035(3) 0.026(3) -0.004(3) 0.007(3) 0.002(3)
C7 0.036(4) 0.036(4) 0.026(3) -0.001(3) 0.006(3) 0.005(3)
C8 0.054(5) 0.128(8) 0.026(4) 0.000(5) 0.006(4) 0.012(6)
C9 0.046(5) 0.125(8) 0.038(4) -0.012(5) 0.009(4) 0.017(5)
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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C4 91.4(3) . . ?
C3 S2 C4 91.4(3) . . ?
C6 S3 C5 91.7(3) . . ?
C7 S4 C5 93.0(3) . . ?
C6 S5 C8 95.9(4) . . ?
C7 S6 C9 100.4(3) . . ?
N1 C1 C2 178.8(8) . . ?
C3 C2 C1 126.9(6) . . ?
C3 C2 S1 118.4(5) . . ?
C1 C2 S1 114.8(5) . . ?
C2 C3 S2 120.8(5) . . ?
C5 C4 S2 120.1(5) . . ?
C5 C4 S1 121.9(5) . . ?
S2 C4 S1 118.0(3) . . ?
C4 C5 S3 120.2(5) . . ?
C4 C5 S4 122.3(5) . . ?
S3 C5 S4 117.5(3) . . ?
C7 C6 S5 126.9(4) . . ?
C7 C6 S3 119.5(5) . . ?
S5 C6 S3 113.4(4) . . ?
C6 C7 S4 117.9(4) . . ?
C6 C7 S6 131.3(5) . . ?
S4 C7 S6 110.8(4) . . ?
C9 C8 S5 118.5(7) . . ?
C8 C9 S6 119.6(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.760(7) . ?
S1 C4 1.852(6) . ?
S2 C3 1.751(6) . ?
S2 C4 1.811(7) . ?
S3 C6 1.803(6) . ?
S3 C5 1.816(7) . ?
S4 C7 1.771(7) . ?
S4 C5 1.843(6) . ?
S5 C6 1.765(7) . ?
S5 C8 1.857(8) . ?
S6 C7 1.797(6) . ?
S6 C9 1.799(9) . ?
N1 C1 1.179(8) . ?
C1 C2 1.473(9) . ?
C2 C3 1.407(9) . ?
C4 C5 1.348(8) . ?
C6 C7 1.412(9) . ?
C8 C9 1.506(12) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21142327
