#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:03:56 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179229 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/49/4314908.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_4314908
loop_
_publ_author_name
'Fabrice Pointillart'
'Thomas Cauchy'
'Yann Le Gal'
'Stéphane Golhen'
'Olivier Cador'
'Lahcène Ouahab'
_publ_contact_author_address
;Organométalliques et Matériaux Moléculaires
UMR 6226 CNRS-UR1 Sciences Chimiques de Rennes
Université de Rennes 1
35042, Rennes Cedex
France
;
_publ_contact_author_email       lacene.ouahab@univ-rennes1.fr
_publ_contact_author_fax         '+33(0)2 23 23 68 40'
_publ_contact_author_name        Ouahab
_publ_contact_author_phone       '+33(0)2 23 23 56 59'
_publ_section_title
;
 Experimental and Theoretical Studies on Photophysical Properties: Tuning
 Redox-Active Amido-Tetrathiafulvalene Derivatives in Paramagnetic
 Coordination Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1947
_journal_page_last               1960
_journal_paper_doi               10.1021/ic9023426
_journal_volume                  49
_journal_year                    2010
_chemical_formula_sum            'C32 H16 Cu F12 N6 O6 S8'
_chemical_formula_weight         1128.53
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.436(5)
_cell_angle_beta                 111.043(8)
_cell_angle_gamma                99.410(8)
_cell_formula_units_Z            1
_cell_length_a                   9.0330(10)
_cell_length_b                   9.7994(17)
_cell_length_c                   12.562(2)
_cell_measurement_reflns_used    3203
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.373
_cell_measurement_theta_min      0.998
_cell_volume                     1021.2(3)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare al, 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.921
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_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  0.0676
_diffrn_reflns_av_sigmaI/netI    0.1040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6258
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             563
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0594
_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)+(0.0536P)²+0.0092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1462
_reflns_number_gt                2110
_reflns_number_total             3867
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9023426_si_002_5.cif
_cod_data_source_block           8
_cod_database_code               4314908
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
C1 C 0.7889(7) 0.3239(8) 0.0024(6) 0.071(2) Uani 1 1 d . . .
H1 H 0.8488 0.3808 -0.0322 0.085 Uiso 1 1 calc R . .
C2 C 0.8213(8) 0.1994(8) 0.0325(6) 0.071(2) Uani 1 1 d . . .
H2 H 0.9048 0.1663 0.0198 0.086 Uiso 1 1 calc R . .
C3 C 0.5933(6) 0.2309(6) 0.1010(5) 0.0488(14) Uani 1 1 d . . .
C4 C 0.4857(7) 0.2170(6) 0.1538(5) 0.0476(14) Uani 1 1 d . . .
C5 C 0.3182(6) 0.1351(6) 0.2735(5) 0.0525(15) Uani 1 1 d . . .
H5 H 0.2741 0.0845 0.3207 0.063 Uiso 1 1 calc R . .
C6 C 0.2840(6) 0.2594(6) 0.2461(5) 0.0455(13) Uani 1 1 d . . .
C7 C 0.1733(6) 0.3378(6) 0.2754(5) 0.0471(14) Uani 1 1 d . . .
C8 C -0.0313(6) 0.3078(6) 0.3661(4) 0.0440(13) Uani 1 1 d . . .
C9 C -0.0841(6) 0.4342(7) 0.3417(5) 0.0577(16) Uani 1 1 d . . .
H9 H -0.0409 0.4946 0.2994 0.069 Uiso 1 1 calc R . .
C10 C -0.2530(7) 0.3790(7) 0.4383(6) 0.0626(17) Uani 1 1 d . . .
H10 H -0.3302 0.4007 0.4653 0.075 Uiso 1 1 calc R . .
C11 C -0.2022(7) 0.2555(6) 0.4612(5) 0.0552(16) Uani 1 1 d . . .
H11 H -0.2474 0.1945 0.5022 0.066 Uiso 1 1 calc R . .
C12 C 0.0528(7) 0.1924(7) 0.8159(5) 0.0567(16) Uani 1 1 d . . .
C13 C 0.1009(6) 0.1473(5) 0.7176(4) 0.0392(12) Uani 1 1 d . . .
C14 C 0.2472(6) 0.2076(6) 0.7135(5) 0.0492(14) Uani 1 1 d . . .
H14 H 0.3155 0.2723 0.7722 0.059 Uiso 1 1 calc R . .
C15 C 0.2966(6) 0.1759(6) 0.6261(5) 0.0405(13) Uani 1 1 d . . .
C16 C 0.4616(7) 0.2512(7) 0.6296(5) 0.0530(15) Uani 1 1 d . . .
N1 N 0.0843(5) 0.2639(5) 0.3308(4) 0.0502(12) Uani 1 1 d . . .
H1N H 0.1016 0.1811 0.3456 0.060 Uiso 1 1 calc R . .
N2 N -0.0886(5) 0.2187(5) 0.4266(4) 0.0462(11) Uani 1 1 d . . .
N3 N -0.1951(6) 0.4701(5) 0.3778(5) 0.0669(15) Uani 1 1 d . . .
O1 O 0.1636(5) 0.4535(5) 0.2478(4) 0.0770(14) Uani 1 1 d . . .
O2 O -0.0069(4) 0.0578(4) 0.6463(3) 0.0428(9) Uani 1 1 d . . .
O3 O 0.2219(4) 0.0948(4) 0.5386(3) 0.0439(9) Uani 1 1 d . . .
F1 F 0.0291(6) 0.0862(5) 0.8751(4) 0.1001(15) Uani 1 1 d . . .
F2 F 0.1507(7) 0.2899(7) 0.8826(4) 0.151(3) Uani 1 1 d . . .
F3 F -0.0869(6) 0.2324(6) 0.7761(4) 0.1140(18) Uani 1 1 d . . .
F4 F 0.5583(4) 0.3039(5) 0.7304(4) 0.0985(15) Uani 1 1 d . . .
F5 F 0.4431(4) 0.3523(4) 0.5588(4) 0.0811(12) Uani 1 1 d . . .
F6 F 0.5373(4) 0.1661(4) 0.5940(3) 0.0771(11) Uani 1 1 d . . .
S1 S 0.6322(2) 0.37702(19) 0.02960(16) 0.0697(5) Uani 1 1 d . . .
S2 S 0.70380(19) 0.10109(18) 0.09563(15) 0.0622(5) Uani 1 1 d . . .
S3 S 0.4448(2) 0.06827(17) 0.22124(15) 0.0608(5) Uani 1 1 d . . .
S4 S 0.37885(19) 0.34957(17) 0.16134(15) 0.0603(5) Uani 1 1 d . . .
Cu1 Cu 0.0000 0.0000 0.5000 0.0422(3) Uani 1 2 d S . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Cu Cu 0.3201 1.2651 '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 C1 S1 117.8(5) . . ?
C1 C2 S2 117.9(5) . . ?
C4 C3 S1 123.4(4) . . ?
C4 C3 S2 122.6(4) . . ?
S1 C3 S2 114.0(3) . . ?
C3 C4 S3 122.6(4) . . ?
C3 C4 S4 122.1(4) . . ?
S3 C4 S4 115.2(3) . . ?
C6 C5 S3 119.3(4) . . ?
C5 C6 C7 130.0(5) . . ?
C5 C6 S4 117.0(4) . . ?
C7 C6 S4 113.1(4) . . ?
O1 C7 N1 125.1(5) . . ?
O1 C7 C6 120.6(5) . . ?
N1 C7 C6 114.3(5) . . ?
N2 C8 N1 114.2(5) . . ?
N2 C8 C9 121.5(5) . . ?
N1 C8 C9 124.4(5) . . ?
N3 C9 C8 121.5(5) . . ?
N3 C10 C11 121.9(5) . . ?
N2 C11 C10 122.2(5) . . ?
F2 C12 F3 107.0(6) . . ?
F2 C12 F1 109.3(6) . . ?
F3 C12 F1 104.1(5) . . ?
F2 C12 C13 114.7(5) . . ?
F3 C12 C13 110.6(5) . . ?
F1 C12 C13 110.6(5) . . ?
O2 C13 C14 127.7(5) . . ?
O2 C13 C12 113.0(4) . . ?
C14 C13 C12 119.3(5) . . ?
C13 C14 C15 122.7(5) . . ?
O3 C15 C14 128.6(4) . . ?
O3 C15 C16 113.2(4) . . ?
C14 C15 C16 118.2(5) . . ?
F4 C16 F5 108.2(5) . . ?
F4 C16 F6 106.8(5) . . ?
F5 C16 F6 106.1(5) . . ?
F4 C16 C15 113.9(5) . . ?
F5 C16 C15 110.2(5) . . ?
F6 C16 C15 111.2(5) . . ?
C7 N1 C8 127.3(5) . . ?
C8 N2 C11 116.4(5) . . ?
C8 N2 Cu1 128.9(3) . . ?
C11 N2 Cu1 114.5(4) . . ?
C9 N3 C10 116.6(5) . . ?
C13 O2 Cu1 123.6(3) . . ?
C15 O3 Cu1 123.3(3) . . ?
C1 S1 C3 94.9(3) . . ?
C2 S2 C3 94.8(3) . . ?
C5 S3 C4 94.4(3) . . ?
C6 S4 C4 93.9(3) . . ?
O2 Cu1 O2 180.000(1) 2_556 . ?
O2 Cu1 O3 93.17(14) 2_556 2_556 ?
O2 Cu1 O3 86.83(14) . 2_556 ?
O2 Cu1 O3 86.83(14) 2_556 . ?
O2 Cu1 O3 93.17(14) . . ?
O3 Cu1 O3 180.0 2_556 . ?
O2 Cu1 N2 91.76(14) 2_556 . ?
O2 Cu1 N2 88.24(14) . . ?
O3 Cu1 N2 91.89(14) 2_556 . ?
O3 Cu1 N2 88.11(14) . . ?
O2 Cu1 N2 88.24(14) 2_556 2_556 ?
O2 Cu1 N2 91.76(14) . 2_556 ?
O3 Cu1 N2 88.11(14) 2_556 2_556 ?
O3 Cu1 N2 91.89(14) . 2_556 ?
N2 Cu1 N2 180.000(1) . 2_556 ?
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
C1 C2 1.328(9) . ?
C1 S1 1.726(6) . ?
C2 S2 1.722(7) . ?
C3 C4 1.351(7) . ?
C3 S1 1.749(6) . ?
C3 S2 1.755(6) . ?
C4 S3 1.745(6) . ?
C4 S4 1.761(6) . ?
C5 C6 1.324(8) . ?
C5 S3 1.717(5) . ?
C6 C7 1.496(7) . ?
C6 S4 1.752(5) . ?
C7 O1 1.196(6) . ?
C7 N1 1.368(6) . ?
C8 N2 1.325(6) . ?
C8 N1 1.395(6) . ?
C8 C9 1.396(8) . ?
C9 N3 1.332(7) . ?
C10 N3 1.338(8) . ?
C10 C11 1.360(8) . ?
C11 N2 1.346(6) . ?
C12 F2 1.256(7) . ?
C12 F3 1.306(7) . ?
C12 F1 1.317(7) . ?
C12 C13 1.532(7) . ?
C13 O2 1.266(6) . ?
C13 C14 1.375(6) . ?
C14 C15 1.376(7) . ?
C15 O3 1.255(6) . ?
C15 C16 1.536(7) . ?
C16 F4 1.297(6) . ?
C16 F5 1.327(7) . ?
C16 F6 1.327(7) . ?
N2 Cu1 2.479(4) . ?
O2 Cu1 1.945(3) . ?
O3 Cu1 1.950(3) . ?
Cu1 O2 1.945(3) 2_556 ?
Cu1 O3 1.950(3) 2_556 ?
Cu1 N2 2.479(4) 2_556 ?
