#------------------------------------------------------------------------------
#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/26/2102684.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_2102684
loop_
_publ_author_name
'Nielsen, Kim T.'
'Harris, Pernille'
'Bechgaard, Klaus'
'Krebs, Frederik C.'
_publ_section_title
;
 Structural study of four complexes of the M-N₂S₂ type
 derived from diethylphenylazothioformamide and the metals palladium,
 platinum, copper and nickel
;
_journal_coeditor_code           BK5045
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              151
_journal_page_last               156
_journal_paper_doi               10.1107/S0108768106047306
_journal_volume                  63
_journal_year                    2007
_chemical_formula_sum            'C22 H30 Cu N6 S2'
_chemical_formula_weight         506.18
_chemical_name_systematic
;
Trans-(di(N,N-diethyl-(2-phenyldiazenyl)thioformamide-\kS,\kN²))copper
;
_space_group_IT_number           92
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4abw 2nw'
_symmetry_space_group_name_H-M   'P 41 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2643(4)
_cell_length_b                   10.2643(4)
_cell_length_c                   22.3519(13)
_cell_measurement_reflns_used    10241
_cell_measurement_temperature    118
_cell_measurement_theta_max      27.956
_cell_measurement_theta_min      2.695
_cell_volume                     2354.90(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material
;
WinGX publication routines (Farrugia, 1999)
;
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      118
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Omega 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  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            16807
_diffrn_reflns_theta_full        28.01
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         2.18
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  0.8492
_exptl_absorpt_correction_T_min  0.6614
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS,ver2.03 (Sheldrick,2001)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Quadratic bi-pyramidal shaped'
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.175
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881, 1132 Fridel pairs'
_refine_ls_abs_structure_Flack   0.012(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0237
_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+0.1079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0702
_reflns_number_gt                2788
_reflns_number_total             2832
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            bk5045.cif
_cod_data_source_block           CuL20
_cod_database_code               2102684
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
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
Cu Cu 0.151860(16) 0.151860(16) 0.0000 0.01397(9) Uani d S 1
S S -0.01348(3) 0.16903(4) 0.067367(18) 0.01868(10) Uani d . 1
C C1 -0.08987(14) 0.29169(14) 0.02823(7) 0.0139(3) Uani d . 1
C C2 -0.27499(14) 0.44307(15) 0.01431(7) 0.0193(3) Uani d . 1
H H2A -0.2115 0.4959 -0.0086 0.023 Uiso calc R 1
H H2B -0.3180 0.5009 0.0437 0.023 Uiso calc R 1
C C3 -0.37665(16) 0.38819(17) -0.02821(8) 0.0244(3) Uani d . 1
H H3A -0.4209 0.4599 -0.0488 0.037 Uiso calc R 1
H H3B -0.4405 0.3373 -0.0055 0.037 Uiso calc R 1
H H3C -0.3341 0.3320 -0.0578 0.037 Uiso calc R 1
C C4 -0.27172(15) 0.28546(16) 0.09915(7) 0.0199(3) Uani d . 1
H H4A -0.2523 0.1912 0.1024 0.024 Uiso calc R 1
H H4B -0.3670 0.2953 0.0941 0.024 Uiso calc R 1
C C5 -0.23001(17) 0.35315(19) 0.15659(8) 0.0293(4) Uani d . 1
H H5A -0.2765 0.3147 0.1906 0.044 Uiso calc R 1
H H5B -0.2507 0.4462 0.1540 0.044 Uiso calc R 1
H H5C -0.1360 0.3421 0.1622 0.044 Uiso calc R 1
C C6 0.12967(13) 0.35602(13) -0.08980(7) 0.0140(3) Uani d . 1
C C7 0.05412(15) 0.41548(14) -0.13431(7) 0.0179(3) Uani d . 1
H H7 -0.0371 0.4257 -0.1290 0.022 Uiso calc R 1
C C8 0.11421(15) 0.45922(15) -0.18616(7) 0.0215(3) Uani d . 1
H H8 0.0631 0.4980 -0.2168 0.026 Uiso calc R 1
C C9 0.24836(16) 0.44715(14) -0.19406(7) 0.0206(3) Uani d . 1
H H9 0.2882 0.4780 -0.2297 0.025 Uiso calc R 1
C C10 0.32348(15) 0.38972(14) -0.14959(7) 0.0180(3) Uani d . 1
H H10 0.4150 0.3818 -0.1546 0.022 Uiso calc R 1
C C11 0.26463(14) 0.34395(14) -0.09783(7) 0.0157(3) Uani d . 1
H H11 0.3161 0.3041 -0.0676 0.019 Uiso calc R 1
N N1 0.07845(11) 0.30528(11) -0.03596(6) 0.0128(2) Uani d . 1
N N2 -0.04083(11) 0.34544(12) -0.02319(5) 0.0142(2) Uani d . 1
N N3 -0.20557(12) 0.33844(12) 0.04624(6) 0.0162(3) Uani d . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu N1 7 . 144.83(7) yes
N1 Cu S 7 7 85.46(4) yes
N1 Cu S . 7 111.39(4) ?
N1 Cu S 7 . 111.39(4) ?
N1 Cu S . . 85.46(4) ?
S Cu S 7 . 123.60(2) yes
C1 S Cu . . 93.44(5) ?
N3 C1 N2 . . 115.62(12) ?
N3 C1 S . . 120.77(11) ?
N2 C1 S . . 123.58(10) ?
N3 C2 C3 . . 111.40(13) ?
N3 C2 H2A . . 109.3 ?
C3 C2 H2A . . 109.3 ?
N3 C2 H2B . . 109.3 ?
C3 C2 H2B . . 109.3 ?
H2A C2 H2B . . 108.0 ?
C2 C3 H3A . . 109.5 ?
C2 C3 H3B . . 109.5 ?
H3A C3 H3B . . 109.5 ?
C2 C3 H3C . . 109.5 ?
H3A C3 H3C . . 109.5 ?
H3B C3 H3C . . 109.5 ?
N3 C4 C5 . . 112.36(13) ?
N3 C4 H4A . . 109.1 ?
C5 C4 H4A . . 109.1 ?
N3 C4 H4B . . 109.1 ?
C5 C4 H4B . . 109.1 ?
H4A C4 H4B . . 107.9 ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C11 . . 119.62(14) ?
C7 C6 N1 . . 124.01(12) ?
C11 C6 N1 . . 116.36(13) ?
C8 C7 C6 . . 119.20(13) ?
C8 C7 H7 . . 120.4 ?
C6 C7 H7 . . 120.4 ?
C7 C8 C9 . . 121.08(14) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C10 C9 C8 . . 119.70(15) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C11 C10 C9 . . 119.92(14) ?
C11 C10 H10 . . 120.0 ?
C9 C10 H10 . . 120.0 ?
C10 C11 C6 . . 120.46(14) ?
C10 C11 H11 . . 119.8 ?
C6 C11 H11 . . 119.8 ?
N2 N1 C6 . . 114.41(11) ?
N2 N1 Cu . . 121.86(9) ?
C6 N1 Cu . . 120.82(9) ?
N1 N2 C1 . . 113.29(12) ?
C1 N3 C4 . . 121.22(12) ?
C1 N3 C2 . . 122.89(12) ?
C4 N3 C2 . . 115.88(11) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu N1 7 1.9219(12) yes
Cu N1 . 1.9219(12) ?
Cu S 7 2.2756(4) yes
Cu S . 2.2756(4) ?
S C1 . 1.7220(15) yes
C1 N3 . 1.3427(18) ?
C1 N2 . 1.3706(18) yes
C2 N3 . 1.4733(18) ?
C2 C3 . 1.520(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 H3A . 0.9800 ?
C3 H3B . 0.9800 ?
C3 H3C . 0.9800 ?
C4 N3 . 1.4682(19) ?
C4 C5 . 1.521(2) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 C7 . 1.401(2) ?
C6 C11 . 1.4024(19) ?
C6 N1 . 1.4128(19) ?
C7 C8 . 1.387(2) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.394(2) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.389(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.387(2) ?
C10 H10 . 0.9500 ?
C11 H11 . 0.9500 ?
N1 N2 . 1.3230(16) yes
