#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/93/4079396.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_4079396
loop_
_publ_author_name
'Chen, Chaohuang'
'Weng, Zhiqiang'
'Hartwig, John F.'
_publ_contact_author
; 
Scott R. Wilson 
University of Illinois 
School of Chemical Sciences, Box 59-1 
505 South Mathews Avenue 
Urbana, Illinois  61801 
USA 
;
_publ_section_title
;
 Synthesis of Copper(I) Thiolate Complexes in the Thioetherification of
 Aryl Halides.
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              8031
_journal_page_last               8037
_journal_paper_doi               10.1021/om300711c
_journal_volume                  31
_journal_year                    2012
_chemical_formula_moiety         'C36 H26 Cu2 N4 S2'
_chemical_formula_sum            'C36 H26 Cu2 N4 S2'
_chemical_formula_weight         705.81
_chemical_name_systematic
; 
? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
; 
2007-07-31   text and data added, srw 
;
_cell_angle_alpha                90.00
_cell_angle_beta                 115.0020(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6762(2)
_cell_length_b                   17.4964(4)
_cell_length_c                   9.9031(2)
_cell_measurement_reflns_used    9688
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      28.54
_cell_measurement_theta_min      2.32
_cell_volume                     1519.47(6)
_computing_cell_refinement       'SAINT V7.23A (Bruker, 2001)'
_computing_data_collection       'APEX2 V2.0-1 (Bruker, 2004)'
_computing_data_reduction        'SAINT V7.23A(Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'XCIF (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'Bruker Kappa/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_wavelength_id  ga44uas
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            27224
_diffrn_reflns_theta_full        29.02
_diffrn_reflns_theta_max         29.02
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_T_max  0.8825
_exptl_absorpt_correction_T_min  0.6996
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SHELXTL/XPREP (Bruker, 2001)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_id                ga44uas
_exptl_crystal_preparation
; 
The data crystal was mounted using oil (Parantone-N, Exxon) to a 
0.3 mm cryo-loop (Hampton Research) with the (1 2 -2) scattering 
planes roughly normal to the spindle axis. 
;
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0365P)²+0.7738P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0720
_refine_ls_wR_factor_ref         0.0761
_reflns_number_gt                3458
_reflns_number_total             4113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om300711c_si_001.cif
_cod_data_source_block           ga44uas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_Hall     '-P 2yb '
_cod_original_sg_symbol_H-M      'P 21/m  '
_cod_database_code               4079396
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
C1 C 0.45039(17) 0.01176(9) 0.26304(17) 0.0215(3) Uani 1 1 d .
C2 C 0.56804(17) 0.01612(9) 0.20931(16) 0.0217(3) Uani 1 1 d .
C3 C 0.7048(2) 0.08984(11) 0.1166(2) 0.0303(4) Uani 1 1 d .
H3 H 0.724(2) 0.1392(13) 0.088(2) 0.036 Uiso 1 1 d .
C4 C 0.7854(2) 0.02611(12) 0.1036(2) 0.0349(4) Uani 1 1 d .
H4 H 0.860(3) 0.0326(12) 0.065(2) 0.042 Uiso 1 1 d .
C5 C 0.7556(2) -0.04425(11) 0.1450(2) 0.0334(4) Uani 1 1 d .
H5 H 0.809(2) -0.0865(13) 0.142(2) 0.040 Uiso 1 1 d .
C6 C 0.64416(19) -0.05090(9) 0.20085(18) 0.0261(3) Uani 1 1 d .
C7 C 0.6050(2) -0.12235(10) 0.2466(2) 0.0316(4) Uani 1 1 d .
H7 H 0.653(3) -0.1658(12) 0.237(2) 0.038 Uiso 1 1 d .
C8 C 0.4974(2) -0.12605(10) 0.3000(2) 0.0320(4) Uani 1 1 d .
H8 H 0.473(3) -0.1748(12) 0.334(2) 0.038 Uiso 1 1 d .
C9 C 0.4160(2) -0.05912(9) 0.30829(18) 0.0265(3) Uani 1 1 d .
C10 C 0.2988(2) -0.06096(11) 0.3568(2) 0.0354(4) Uani 1 1 d .
H10 H 0.277(2) -0.1039(13) 0.386(2) 0.043 Uiso 1 1 d .
C11 C 0.2244(2) 0.00512(11) 0.3579(2) 0.0384(4) Uani 1 1 d .
H11 H 0.138(3) 0.0051(13) 0.381(2) 0.046 Uiso 1 1 d .
C12 C 0.2668(2) 0.07332(10) 0.3122(2) 0.0322(4) Uani 1 1 d .
H12 H 0.215(2) 0.1204(13) 0.311(2) 0.039 Uiso 1 1 d .
C13 C 0.1404(3) 0.2500 -0.0104(2) 0.0226(4) Uani 1 2 d S
C14 C 0.0215(3) 0.2500 -0.1535(3) 0.0302(5) Uani 1 2 d S
H14 H 0.048(3) 0.2500 -0.235(3) 0.036 Uiso 1 2 d S
C15 C -0.1294(3) 0.2500 -0.1746(3) 0.0336(5) Uani 1 2 d S
H15 H -0.205(4) 0.2500 -0.272(4) 0.040 Uiso 1 2 d S
C16 C -0.1658(3) 0.2500 -0.0529(3) 0.0325(5) Uani 1 2 d S
H16 H -0.267(4) 0.2500 -0.067(3) 0.039 Uiso 1 2 d S
C17 C -0.0488(3) 0.2500 0.0899(3) 0.0301(5) Uani 1 2 d S
H17 H -0.073(3) 0.2500 0.174(3) 0.036 Uiso 1 2 d S
C18 C 0.1022(3) 0.2500 0.1112(3) 0.0263(5) Uani 1 2 d S
H18 H 0.174(3) 0.2500 0.201(3) 0.032 Uiso 1 2 d S
C19 C 0.8048(3) 0.2500 0.4360(2) 0.0235(4) Uani 1 2 d S
C20 C 0.8845(2) 0.18160(10) 0.45037(18) 0.0271(3) Uani 1 1 d .
H20 H 0.834(2) 0.1342(12) 0.440(2) 0.033 Uiso 1 1 d .
C21 C 1.0384(2) 0.18181(11) 0.4795(2) 0.0313(4) Uani 1 1 d .
H21 H 1.089(2) 0.1335(13) 0.492(2) 0.038 Uiso 1 1 d .
C22 C 1.1163(3) 0.2500 0.4944(3) 0.0336(6) Uani 1 2 d S
H22 H 1.213(4) 0.2500 0.514(3) 0.040 Uiso 1 2 d S
N1 N 0.37745(15) 0.07785(8) 0.26617(15) 0.0248(3) Uani 1 1 d .
N2 N 0.59791(15) 0.08604(8) 0.16813(15) 0.0240(3) Uani 1 1 d .
S1 S 0.33104(7) 0.2500 0.00989(6) 0.02469(12) Uani 1 2 d S
S2 S 0.61203(6) 0.2500 0.41099(6) 0.02433(12) Uani 1 2 d S
Cu1 Cu 0.47205(2) 0.172250(11) 0.20622(2) 0.02717(7) 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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 -1.00 1.00 0.1000
-1.00 -1.00 -2.00 0.0300
1.00 1.00 2.00 0.0600
0.00 -1.00 -1.00 0.0500
2.00 -1.00 -1.00 0.0900
-1.00 -1.00 2.00 0.0900
0.00 1.00 0.00 0.1000
0.00 2.00 -1.00 0.0900
2.00 5.00 -1.00 0.0900
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
N1 C1 C9 123.18(14) . .
N1 C1 C2 117.33(13) . .
C9 C1 C2 119.48(14) . .
N2 C2 C6 123.36(14) . .
N2 C2 C1 117.24(13) . .
C6 C2 C1 119.40(14) . .
N2 C3 C4 123.26(17) . .
N2 C3 H3 116.0(13) . .
C4 C3 H3 120.8(13) . .
C5 C4 C3 119.65(16) . .
C5 C4 H4 121.1(13) . .
C3 C4 H4 119.2(13) . .
C4 C5 C6 119.04(16) . .
C4 C5 H5 122.2(14) . .
C6 C5 H5 118.7(14) . .
C5 C6 C2 117.48(15) . .
C5 C6 C7 122.98(16) . .
C2 C6 C7 119.53(15) . .
C8 C7 C6 120.99(16) . .
C8 C7 H7 120.5(13) . .
C6 C7 H7 118.5(13) . .
C7 C8 C9 121.01(16) . .
C7 C8 H8 121.0(13) . .
C9 C8 H8 118.0(13) . .
C10 C9 C1 117.55(15) . .
C10 C9 C8 122.88(16) . .
C1 C9 C8 119.55(15) . .
C11 C10 C9 119.18(16) . .
C11 C10 H10 122.3(15) . .
C9 C10 H10 118.6(15) . .
C10 C11 C12 119.55(16) . .
C10 C11 H11 121.2(14) . .
C12 C11 H11 119.0(14) . .
N1 C12 C11 123.36(16) . .
N1 C12 H12 116.0(13) . .
C11 C12 H12 120.6(13) . .
C14 C13 C18 117.9(2) . .
C14 C13 S1 119.13(17) . .
C18 C13 S1 122.95(18) . .
C15 C14 C13 121.1(2) . .
C15 C14 H14 121.3(18) . .
C13 C14 H14 117.7(18) . .
C14 C15 C16 120.4(2) . .
C14 C15 H15 118.1(19) . .
C16 C15 H15 121.5(19) . .
C15 C16 C17 119.1(2) . .
C15 C16 H16 120.5(19) . .
C17 C16 H16 120.4(19) . .
C18 C17 C16 120.6(2) . .
C18 C17 H17 119.7(18) . .
C16 C17 H17 119.7(18) . .
C17 C18 C13 120.9(2) . .
C17 C18 H18 119.4(19) . .
C13 C18 H18 119.7(19) . .
C20 C19 C20 117.8(2) . 4_565
C20 C19 S2 121.07(11) . .
C20 C19 S2 121.07(11) 4_565 .
C21 C20 C19 120.96(17) . .
C21 C20 H20 118.8(12) . .
C19 C20 H20 120.3(12) . .
C22 C21 C20 120.70(18) . .
C22 C21 H21 121.2(12) . .
C20 C21 H21 118.0(12) . .
C21 C22 C21 118.9(2) 4_565 .
C21 C22 H22 120.55(12) 4_565 .
C21 C22 H22 120.55(12) . .
C12 N1 C1 117.17(14) . .
C12 N1 Cu1 130.97(11) . .
C1 N1 Cu1 111.76(10) . .
C3 N2 C2 117.21(14) . .
C3 N2 Cu1 130.08(12) . .
C2 N2 Cu1 112.65(10) . .
C13 S1 Cu1 108.34(6) . .
C13 S1 Cu1 108.34(6) . 4_565
Cu1 S1 Cu1 72.84(2) . 4_565
C19 S2 Cu1 108.07(6) . .
C19 S2 Cu1 108.06(6) . 4_565
Cu1 S2 Cu1 71.090(19) . 4_565
N2 Cu1 N1 80.69(5) . .
N2 Cu1 S1 117.58(4) . .
N1 Cu1 S1 122.30(4) . .
N2 Cu1 S2 114.31(4) . .
N1 Cu1 S2 112.05(4) . .
S1 Cu1 S2 108.011(14) . .
N2 Cu1 Cu1 136.75(4) . 4_565
N1 Cu1 Cu1 142.13(4) . 4_565
S1 Cu1 Cu1 53.579(10) . 4_565
S2 Cu1 Cu1 54.455(9) . 4_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.362(2) .
C1 C9 1.405(2) .
C1 C2 1.448(2) .
C2 N2 1.359(2) .
C2 C6 1.406(2) .
C3 N2 1.334(2) .
C3 C4 1.398(3) .
C3 H3 0.95(2) .
C4 C5 1.366(3) .
C4 H4 0.96(2) .
C5 C6 1.410(2) .
C5 H5 0.91(2) .
C6 C7 1.434(2) .
C7 C8 1.353(3) .
C7 H7 0.92(2) .
C8 C9 1.433(2) .
C8 H8 0.98(2) .
C9 C10 1.407(2) .
C10 C11 1.365(3) .
C10 H10 0.86(2) .
C11 C12 1.397(3) .
C11 H11 0.96(2) .
C12 N1 1.332(2) .
C12 H12 0.96(2) .
C13 C14 1.398(3) .
C13 C18 1.401(3) .
C13 S1 1.769(2) .
C14 C15 1.385(4) .
C14 H14 0.94(3) .
C15 C16 1.391(4) .
C15 H15 0.93(3) .
C16 C17 1.388(4) .
C16 H16 0.93(3) .
C17 C18 1.385(3) .
C17 H17 0.96(3) .
C18 H18 0.87(3) .
C19 C20 1.398(2) .
C19 C20 1.398(2) 4_565
C19 S2 1.775(2) .
C20 C21 1.392(2) .
C20 H20 0.94(2) .
C21 C22 1.385(2) .
C21 H21 0.96(2) .
C22 C21 1.385(2) 4_565
C22 H22 0.87(3) .
N1 Cu1 2.0923(13) .
N2 Cu1 2.0710(14) .
S1 Cu1 2.2913(5) .
S1 Cu1 2.2913(5) 4_565
S2 Cu1 2.3400(5) .
S2 Cu1 2.3400(5) 4_565
Cu1 Cu1 2.7207(4) 4_565
