#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:03:56 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179229 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/49/4314909.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_4314909
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            'C34 H18 Cu F12 N4 O6 S8'
_chemical_formula_weight         1126.54
_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                89.624(10)
_cell_angle_beta                 110.193(10)
_cell_angle_gamma                101.977(10)
_cell_formula_units_Z            1
_cell_length_a                   9.1870(10)
_cell_length_b                   9.9100(10)
_cell_length_c                   12.6040(10)
_cell_measurement_reflns_used    4289
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1050.9(2)
_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 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0558
_diffrn_reflns_av_sigmaI/netI    0.0838
_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       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8246
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         6.80
_exptl_absorpt_coefficient_mu    1.021
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.780
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             563
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     21
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0565
_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)+(0.0830P)²+0.3320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1724
_reflns_number_gt                2647
_reflns_number_total             4723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic9023426_si_002_6.cif
_cod_data_source_block           9
_cod_original_cell_volume        1050.88(18)
_cod_database_code               4314909
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 0.2155(8) -0.3318(7) -0.4948(5) 0.0858(18) Uani 1 1 d . . .
H1 H 0.1591 -0.3894 -0.4571 0.103 Uiso 1 1 calc R . .
C2 C 0.1801(7) -0.2117(8) -0.5263(5) 0.0828(17) Uani 1 1 d . . .
H2 H 0.0971 -0.1831 -0.5132 0.099 Uiso 1 1 calc R . .
C3 C 0.4052(6) -0.2335(5) -0.5972(4) 0.0601(12) Uani 1 1 d . . .
C4 C 0.5081(6) -0.2198(5) -0.6525(4) 0.0587(12) Uani 1 1 d . . .
C5 C 0.6762(6) -0.1345(5) -0.7751(4) 0.0587(12) Uani 1 1 d . . .
H5 H 0.7217 -0.0834 -0.8223 0.070 Uiso 1 1 calc R . .
C6 C 0.7068(5) -0.2587(5) -0.7461(4) 0.0526(10) Uani 1 1 d . . .
C7 C 0.8160(6) -0.3324(5) -0.7729(4) 0.0557(11) Uani 1 1 d . . .
C8 C 1.0172(5) -0.3028(5) -0.8674(4) 0.0523(10) Uani 1 1 d . . .
C9 C 1.0730(6) -0.4220(5) -0.8324(5) 0.0674(13) Uani 1 1 d . . .
H9 H 1.0333 -0.4805 -0.7861 0.081 Uiso 1 1 calc R . .
C10 C 1.1893(7) -0.4499(6) -0.8690(5) 0.0809(17) Uani 1 1 d . . .
H10 H 1.2298 -0.5284 -0.8473 0.097 Uiso 1 1 calc R . .
C11 C 1.2460(7) -0.3616(6) -0.9379(5) 0.0735(15) Uani 1 1 d . . .
H11 H 1.3240 -0.3791 -0.9639 0.088 Uiso 1 1 calc R . .
C12 C 1.1831(6) -0.2471(5) -0.9667(4) 0.0628(12) Uani 1 1 d . . .
H12 H 1.2209 -0.1872 -1.0130 0.075 Uiso 1 1 calc R . .
C17 C 0.5302(6) -0.2413(5) -1.1286(4) 0.0616(12) Uani 1 1 d . . .
C16 C 0.6947(5) -0.1669(5) -1.1277(4) 0.0496(10) Uani 1 1 d . A .
C15 C 0.7403(6) -0.1945(5) -1.2177(4) 0.0564(11) Uani 1 1 d . . .
H15 H 0.6680 -0.2536 -1.2785 0.068 Uiso 1 1 calc R . .
C14 C 0.8893(5) -0.1375(5) -1.2205(4) 0.0498(10) Uani 1 1 d . A .
C13 C 0.9329(6) -0.1814(6) -1.3208(5) 0.0722(16) Uani 1 1 d D . .
F3A F 1.045(2) -0.2471(17) -1.2897(14) 0.131(6) Uani 0.72(3) 1 d PD A 1
F2A F 0.8141(16) -0.255(2) -1.4010(13) 0.181(7) Uani 0.72(3) 1 d PD A 1
F1A F 0.9830(16) -0.0722(10) -1.3673(9) 0.096(3) Uani 0.72(3) 1 d PD A 1
F3B F 1.0839(18) -0.190(3) -1.281(3) 0.090(8) Uani 0.28(3) 1 d PD A 2
F1B F 0.912(5) -0.100(3) -1.402(2) 0.134(17) Uani 0.28(3) 1 d PD A 2
F2B F 0.852(4) -0.3071(17) -1.360(3) 0.109(10) Uani 0.28(3) 1 d PD A 2
N1 N 0.9016(5) -0.2622(4) -0.8339(3) 0.0606(10) Uani 1 1 d . . .
H1A H 0.8817 -0.1830 -0.8542 0.073 Uiso 1 1 calc R . .
N2 N 1.0717(5) -0.2161(4) -0.9328(3) 0.0578(10) Uani 1 1 d . . .
O1 O 0.8278(5) -0.4457(4) -0.7386(4) 0.0831(12) Uani 1 1 d . . .
O2 O 1.0022(4) -0.0558(3) -1.1480(2) 0.0506(7) Uani 1 1 d . . .
O3 O 0.7763(3) -0.0903(3) -1.0384(3) 0.0519(7) Uani 1 1 d . . .
S1 S 0.3665(2) -0.37954(17) -0.52428(14) 0.0794(4) Uani 1 1 d . . .
S2 S 0.29555(19) -0.10953(16) -0.59328(13) 0.0752(4) Uani 1 1 d . . .
S4 S 0.61119(17) -0.34839(14) -0.66061(12) 0.0686(4) Uani 1 1 d . . .
S3 S 0.55115(19) -0.07153(14) -0.72310(13) 0.0722(4) Uani 1 1 d . . .
Cu1 Cu 1.0000 0.0000 -1.0000 0.0496(2) Uani 1 2 d S . .
F5 F 0.5445(4) -0.3506(4) -1.0683(4) 0.1020(12) Uani 1 1 d . . .
F4 F 0.4287(4) -0.2827(5) -1.2309(3) 0.1033(12) Uani 1 1 d . . .
F6 F 0.4663(4) -0.1616(4) -1.0833(3) 0.0929(11) Uani 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'
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'
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'
F F 0.0171 0.0103 '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 119.0(4) . . ?
C1 C2 S2 117.0(4) . . ?
C4 C3 S1 122.5(4) . . ?
C4 C3 S2 123.5(4) . . ?
S1 C3 S2 114.1(3) . . ?
C3 C4 S3 122.7(4) . . ?
C3 C4 S4 122.9(4) . . ?
S3 C4 S4 114.4(2) . . ?
C6 C5 S3 118.6(3) . . ?
C5 C6 C7 129.6(4) . . ?
C5 C6 S4 117.1(3) . . ?
C7 C6 S4 113.3(3) . . ?
O1 C7 N1 124.5(4) . . ?
O1 C7 C6 119.9(4) . . ?
N1 C7 C6 115.5(4) . . ?
N2 C8 C9 123.1(4) . . ?
N2 C8 N1 114.2(4) . . ?
C9 C8 N1 122.6(4) . . ?
C10 C9 C8 117.4(5) . . ?
C9 C10 C11 120.1(5) . . ?
C12 C11 C10 117.5(5) . . ?
N2 C12 C11 124.3(5) . . ?
F4 C17 F6 106.8(5) . . ?
F4 C17 F5 108.4(5) . . ?
F6 C17 F5 107.6(4) . . ?
F4 C17 C16 113.0(4) . . ?
F6 C17 C16 111.8(4) . . ?
F5 C17 C16 109.1(4) . . ?
O3 C16 C15 127.7(4) . . ?
O3 C16 C17 113.4(4) . . ?
C15 C16 C17 118.9(4) . . ?
C16 C15 C14 122.4(4) . . ?
O2 C14 C15 128.5(4) . . ?
O2 C14 C13 112.7(4) . . ?
C15 C14 C13 118.7(4) . . ?
F1B C13 F3A 124.2(15) . . ?
F1B C13 F2A 77.8(14) . . ?
F3A C13 F2A 108.5(9) . . ?
F1B C13 F2B 110.0(13) . . ?
F3A C13 F2B 80.0(13) . . ?
F2A C13 F2B 34.6(12) . . ?
F1B C13 F1A 29.0(17) . . ?
F3A C13 F1A 106.6(8) . . ?
F2A C13 F1A 105.6(9) . . ?
F2B C13 F1A 134.1(13) . . ?
F1B C13 F3B 109.0(13) . . ?
F3A C13 F3B 26.2(12) . . ?
F2A C13 F3B 129.9(15) . . ?
F2B C13 F3B 105.6(12) . . ?
F1A C13 F3B 84.8(16) . . ?
F1B C13 C14 114.8(12) . . ?
F3A C13 C14 112.4(8) . . ?
F2A C13 C14 113.5(7) . . ?
F2B C13 C14 109.0(11) . . ?
F1A C13 C14 109.8(6) . . ?
F3B C13 C14 108.0(14) . . ?
C7 N1 C8 128.3(4) . . ?
C12 N2 C8 117.5(4) . . ?
C12 N2 Cu1 113.2(3) . . ?
C8 N2 Cu1 129.3(3) . . ?
C14 O2 Cu1 123.8(3) . . ?
C16 O3 Cu1 124.2(3) . . ?
C1 S1 C3 94.9(3) . . ?
C2 S2 C3 94.6(3) . . ?
C6 S4 C4 94.8(2) . . ?
C5 S3 C4 94.9(2) . . ?
O3 Cu1 O3 180.0 . 2_753 ?
O3 Cu1 O2 87.25(12) . 2_753 ?
O3 Cu1 O2 92.75(12) 2_753 2_753 ?
O3 Cu1 O2 92.75(12) . . ?
O3 Cu1 O2 87.25(12) 2_753 . ?
O2 Cu1 O2 180.000(1) 2_753 . ?
O3 Cu1 N2 89.11(13) . . ?
O3 Cu1 N2 90.89(13) 2_753 . ?
O2 Cu1 N2 91.72(12) 2_753 . ?
O2 Cu1 N2 88.28(12) . . ?
O3 Cu1 N2 90.89(13) . 2_753 ?
O3 Cu1 N2 89.11(13) 2_753 2_753 ?
O2 Cu1 N2 88.28(12) 2_753 2_753 ?
O2 Cu1 N2 91.72(12) . 2_753 ?
N2 Cu1 N2 180.000(1) . 2_753 ?
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 1.321(9) . ?
C1 S1 1.708(6) . ?
C2 S2 1.739(6) . ?
C3 C4 1.340(6) . ?
C3 S1 1.750(5) . ?
C3 S2 1.754(5) . ?
C4 S3 1.758(5) . ?
C4 S4 1.761(5) . ?
C5 C6 1.339(7) . ?
C5 S3 1.721(5) . ?
C6 C7 1.481(6) . ?
C6 S4 1.744(4) . ?
C7 O1 1.212(6) . ?
C7 N1 1.370(6) . ?
C8 N2 1.329(6) . ?
C8 C9 1.393(7) . ?
C8 N1 1.399(5) . ?
C9 C10 1.377(7) . ?
C10 C11 1.380(8) . ?
C11 C12 1.369(7) . ?
C12 N2 1.325(5) . ?
C17 F4 1.311(6) . ?
C17 F6 1.313(6) . ?
C17 F5 1.321(6) . ?
C17 C16 1.534(6) . ?
C16 O3 1.263(5) . ?
C16 C15 1.386(6) . ?
C15 C14 1.380(6) . ?
C14 O2 1.255(5) . ?
C14 C13 1.542(6) . ?
C13 F1B 1.281(13) . ?
C13 F3A 1.281(10) . ?
C13 F2A 1.291(9) . ?
C13 F2B 1.310(13) . ?
C13 F1A 1.303(9) . ?
C13 F3B 1.322(13) . ?
N2 Cu1 2.432(4) . ?
O2 Cu1 1.957(3) . ?
O3 Cu1 1.953(3) . ?
Cu1 O3 1.953(3) 2_753 ?
Cu1 O2 1.957(3) 2_753 ?
Cu1 N2 2.432(4) 2_753 ?
