#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:12:28 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179050 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/12/4301246.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_4301246
loop_
_publ_author_name
'Stanislav Groysman'
'R. H. Holm'
_publ_section_title
;
A Series of Mononuclear Quasi-Two-Coordinate Copper(I) Complexes Employing
a Sterically Demanding Thiolate Ligand
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              621
_journal_page_last               627
_journal_paper_doi               10.1021/ic801836k
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C43 H57 Cu N'
_chemical_formula_weight         651.44
_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                112.348(5)
_cell_angle_beta                 102.337(5)
_cell_angle_gamma                90.850(5)
_cell_formula_units_Z            2
_cell_length_a                   12.249(5)
_cell_length_b                   12.703(5)
_cell_length_c                   13.849(5)
_cell_measurement_reflns_used    5762
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.811
_cell_measurement_theta_min      2.391
_cell_volume                     1936.0(13)
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Smart APEX 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  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10934
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  0.8661
_exptl_absorpt_correction_T_min  0.7562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             702
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.040
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     419
_refine_ls_number_reflns         6789
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0820P)²+0.9032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1405
_reflns_number_gt                5860
_reflns_number_total             6789
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801836k_si_002_6.cif
_cod_data_source_block           6
_cod_database_code               4301246
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
Cu1 Cu 0.73505(2) 0.30919(2) 0.36255(2) 0.03686(13) Uani 1 1 d . . .
C1 C 0.77950(19) 0.17065(19) 0.26938(18) 0.0318(5) Uani 1 1 d . . .
N1 N 0.68683(17) 0.44777(17) 0.45801(17) 0.0374(5) Uani 1 1 d . . .
C8 C 0.9016(2) 0.1520(2) 0.50065(19) 0.0379(5) Uani 1 1 d . . .
C6 C 0.7856(2) 0.1510(2) 0.16332(19) 0.0349(5) Uani 1 1 d . . .
C13 C 0.7697(2) 0.2471(2) 0.12494(19) 0.0378(6) Uani 1 1 d . . .
C2 C 0.80756(19) 0.0804(2) 0.30320(18) 0.0325(5) Uani 1 1 d . . .
C3 C 0.8361(2) -0.0230(2) 0.2345(2) 0.0396(6) Uani 1 1 d . . .
H3 H 0.8550 -0.0817 0.2599 0.048 Uiso 1 1 calc R . .
C7 C 0.8077(2) 0.09408(19) 0.41571(19) 0.0345(5) Uani 1 1 d . . .
C9 C 0.8991(2) 0.1616(2) 0.6045(2) 0.0476(7) Uani 1 1 d . . .
H9 H 0.9624 0.2003 0.6618 0.057 Uiso 1 1 calc R . .
C12 C 0.7153(2) 0.0477(2) 0.4366(2) 0.0387(5) Uani 1 1 d . . .
C37 C 0.6676(2) 0.4550(2) 0.5526(2) 0.0410(6) Uani 1 1 d . . .
C28 C 1.0032(2) 0.2041(2) 0.4821(2) 0.0453(6) Uani 1 1 d . . .
H28 H 0.9954 0.1768 0.4028 0.054 Uiso 1 1 calc R . .
C18 C 0.6625(2) 0.2653(2) 0.0780(2) 0.0442(6) Uani 1 1 d . . .
C11 C 0.7173(2) 0.0607(3) 0.5415(2) 0.0488(7) Uani 1 1 d . . .
H11 H 0.6539 0.0298 0.5551 0.059 Uiso 1 1 calc R . .
C10 C 0.8082(3) 0.1171(3) 0.6266(2) 0.0538(7) Uani 1 1 d . . .
C38 C 0.6322(2) 0.5528(2) 0.6214(2) 0.0489(7) Uani 1 1 d . . .
H38 H 0.6187 0.5560 0.6875 0.059 Uiso 1 1 calc R . .
C31 C 0.6123(2) -0.0141(2) 0.3462(2) 0.0431(6) Uani 1 1 d . . .
H31 H 0.6357 -0.0340 0.2770 0.052 Uiso 1 1 calc R . .
C39 C 0.6168(3) 0.6449(2) 0.5925(3) 0.0542(7) Uani 1 1 d . . .
H39 H 0.5929 0.7126 0.6386 0.065 Uiso 1 1 calc R . .
C41 C 0.6709(2) 0.5387(2) 0.4298(2) 0.0417(6) Uani 1 1 d . . .
C40 C 0.6366(2) 0.6380(2) 0.4964(3) 0.0506(7) Uani 1 1 d . . .
H40 H 0.6267 0.7012 0.4757 0.061 Uiso 1 1 calc R . .
C5 C 0.8119(2) 0.0467(2) 0.0945(2) 0.0424(6) Uani 1 1 d . . .
H5 H 0.8127 0.0353 0.0228 0.051 Uiso 1 1 calc R . .
C17 C 0.6514(3) 0.3566(2) 0.0445(2) 0.0565(8) Uani 1 1 d . . .
H17 H 0.5788 0.3689 0.0121 0.068 Uiso 1 1 calc R . .
C14 C 0.8647(3) 0.3185(2) 0.1375(2) 0.0481(7) Uani 1 1 d . . .
C43 C 0.6859(3) 0.3535(3) 0.5821(2) 0.0572(8) Uani 1 1 d . . .
H43A H 0.6478 0.2840 0.5214 0.086 Uiso 1 1 calc R . .
H43B H 0.6553 0.3637 0.6446 0.086 Uiso 1 1 calc R . .
H43C H 0.7666 0.3465 0.5997 0.086 Uiso 1 1 calc R . .
C4 C 0.8369(2) -0.0402(2) 0.1300(2) 0.0440(6) Uani 1 1 d . . .
H4 H 0.8545 -0.1111 0.0829 0.053 Uiso 1 1 calc R . .
C25 C 0.9820(3) 0.2969(3) 0.1844(3) 0.0611(8) Uani 1 1 d . . .
H25 H 0.9708 0.2384 0.2144 0.073 Uiso 1 1 calc R . .
C42 C 0.6913(3) 0.5278(3) 0.3237(2) 0.0552(7) Uani 1 1 d . . .
H42A H 0.7567 0.4856 0.3109 0.083 Uiso 1 1 calc R . .
H42B H 0.7056 0.6043 0.3244 0.083 Uiso 1 1 calc R . .
H42C H 0.6251 0.4865 0.2663 0.083 Uiso 1 1 calc R . .
C15 C 0.8485(3) 0.4093(3) 0.1034(2) 0.0612(9) Uani 1 1 d . . .
H15 H 0.9121 0.4588 0.1123 0.073 Uiso 1 1 calc R . .
C32 C 0.5210(2) 0.0669(3) 0.3466(3) 0.0556(7) Uani 1 1 d . . .
H32A H 0.4551 0.0265 0.2884 0.083 Uiso 1 1 calc R . .
H32B H 0.5497 0.1331 0.3360 0.083 Uiso 1 1 calc R . .
H32C H 0.4997 0.0929 0.4156 0.083 Uiso 1 1 calc R . .
C19 C 0.5588(2) 0.1881(2) 0.0619(2) 0.0511(7) Uani 1 1 d . . .
H19 H 0.5845 0.1276 0.0886 0.061 Uiso 1 1 calc R . .
C33 C 0.5681(3) -0.1256(3) 0.3482(3) 0.0581(8) Uani 1 1 d . . .
H33A H 0.6287 -0.1752 0.3477 0.087 Uiso 1 1 calc R . .
H33B H 0.5064 -0.1643 0.2849 0.087 Uiso 1 1 calc R . .
H33C H 0.5407 -0.1092 0.4135 0.087 Uiso 1 1 calc R . .
C29 C 1.1130(2) 0.1680(3) 0.5305(3) 0.0556(7) Uani 1 1 d . . .
H29A H 1.1277 0.2029 0.6091 0.083 Uiso 1 1 calc R . .
H29B H 1.1750 0.1935 0.5073 0.083 Uiso 1 1 calc R . .
H29C H 1.1068 0.0844 0.5063 0.083 Uiso 1 1 calc R . .
C21 C 0.4995(4) 0.1276(3) -0.0563(3) 0.0843(12) Uani 1 1 d . . .
H21A H 0.4711 0.1844 -0.0847 0.126 Uiso 1 1 calc R . .
H21B H 0.4367 0.0743 -0.0638 0.126 Uiso 1 1 calc R . .
H21C H 0.5527 0.0853 -0.0964 0.126 Uiso 1 1 calc R . .
C24 C 0.7223(8) 0.5069(5) -0.0820(5) 0.204(5) Uani 1 1 d . . .
H24A H 0.7255 0.5677 -0.1057 0.245 Uiso 1 1 calc R . .
H24B H 0.7134 0.4297 -0.1322 0.245 Uiso 1 1 calc R . .
C30 C 1.0097(3) 0.3346(3) 0.5281(4) 0.0773(11) Uani 1 1 d . . .
H30A H 0.9394 0.3582 0.4974 0.116 Uiso 1 1 calc R . .
H30B H 1.0726 0.3657 0.5101 0.116 Uiso 1 1 calc R . .
H30C H 1.0212 0.3636 0.6064 0.116 Uiso 1 1 calc R . .
C20 C 0.4768(3) 0.2523(4) 0.1274(3) 0.0811(11) Uani 1 1 d . . .
H20A H 0.5162 0.2898 0.2034 0.122 Uiso 1 1 calc R . .
H20B H 0.4147 0.1980 0.1198 0.122 Uiso 1 1 calc R . .
H20C H 0.4470 0.3101 0.1011 0.122 Uiso 1 1 calc R . .
C16 C 0.7437(4) 0.4293(3) 0.0574(2) 0.0663(10) Uani 1 1 d . . .
C34 C 0.8063(4) 0.1251(4) 0.7389(3) 0.0814(12) Uani 1 1 d . . .
H34 H 0.7273 0.1378 0.7451 0.098 Uiso 1 1 calc R . .
C22 C 0.7304(5) 0.5299(3) 0.0216(3) 0.1045(17) Uani 1 1 d . . .
H22 H 0.6470 0.5225 0.0116 0.125 Uiso 1 1 calc R . .
C36 C 0.8240(4) 0.0096(4) 0.7477(3) 0.0856(12) Uani 1 1 d . . .
H36A H 0.8987 -0.0109 0.7373 0.128 Uiso 1 1 calc R . .
H36B H 0.7666 -0.0493 0.6923 0.128 Uiso 1 1 calc R . .
H36C H 0.8181 0.0152 0.8189 0.128 Uiso 1 1 calc R . .
C26 C 1.0477(4) 0.4006(4) 0.2785(4) 0.1079(17) Uani 1 1 d . . .
H26A H 1.1210 0.3804 0.3071 0.162 Uiso 1 1 calc R . .
H26B H 1.0058 0.4262 0.3349 0.162 Uiso 1 1 calc R . .
H26C H 1.0587 0.4625 0.2545 0.162 Uiso 1 1 calc R . .
C27 C 1.0471(4) 0.2439(5) 0.1013(5) 0.128(2) Uani 1 1 d . . .
H27A H 1.0046 0.1729 0.0461 0.192 Uiso 1 1 calc R . .
H27B H 1.1196 0.2268 0.1352 0.192 Uiso 1 1 calc R . .
H27C H 1.0598 0.2972 0.0680 0.192 Uiso 1 1 calc R . .
C23 C 0.7439(6) 0.6390(4) 0.1070(4) 0.139(3) Uani 1 1 d . . .
H23A H 0.8237 0.6605 0.1436 0.209 Uiso 1 1 calc R . .
H23B H 0.7008 0.6362 0.1582 0.209 Uiso 1 1 calc R . .
H23C H 0.7166 0.6959 0.0782 0.209 Uiso 1 1 calc R . .
C35 C 0.8744(6) 0.2215(5) 0.8257(4) 0.142(3) Uani 1 1 d . . .
H35A H 0.9540 0.2102 0.8299 0.213 Uiso 1 1 calc R . .
H35B H 0.8563 0.2287 0.8934 0.213 Uiso 1 1 calc R . .
H35C H 0.8594 0.2913 0.8131 0.213 Uiso 1 1 calc R . .
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'
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
C1 Cu1 N1 178.48(9) . . ?
C6 C1 C2 115.8(2) . . ?
C6 C1 Cu1 122.83(17) . . ?
C2 C1 Cu1 121.37(17) . . ?
C37 N1 C41 118.8(2) . . ?
C37 N1 Cu1 120.90(17) . . ?
C41 N1 Cu1 120.32(17) . . ?
C7 C8 C9 118.5(2) . . ?
C7 C8 C28 121.5(2) . . ?
C9 C8 C28 120.0(2) . . ?
C5 C6 C1 121.9(2) . . ?
C5 C6 C13 118.8(2) . . ?
C1 C6 C13 119.3(2) . . ?
C18 C13 C14 120.5(2) . . ?
C18 C13 C6 120.9(2) . . ?
C14 C13 C6 118.6(2) . . ?
C3 C2 C1 121.9(2) . . ?
C3 C2 C7 118.0(2) . . ?
C1 C2 C7 120.1(2) . . ?
C4 C3 C2 120.3(2) . . ?
C12 C7 C8 119.6(2) . . ?
C12 C7 C2 120.2(2) . . ?
C8 C7 C2 120.2(2) . . ?
C10 C9 C8 122.7(3) . . ?
C11 C12 C7 119.4(2) . . ?
C11 C12 C31 120.1(2) . . ?
C7 C12 C31 120.6(2) . . ?
N1 C37 C38 121.8(2) . . ?
N1 C37 C43 117.8(2) . . ?
C38 C37 C43 120.4(2) . . ?
C8 C28 C30 111.2(3) . . ?
C8 C28 C29 112.2(2) . . ?
C30 C28 C29 109.1(2) . . ?
C13 C18 C17 119.0(3) . . ?
C13 C18 C19 121.5(2) . . ?
C17 C18 C19 119.5(3) . . ?
C10 C11 C12 122.4(3) . . ?
C9 C10 C11 117.5(3) . . ?
C9 C10 C34 122.8(3) . . ?
C11 C10 C34 119.7(3) . . ?
C39 C38 C37 119.1(3) . . ?
C33 C31 C12 113.5(2) . . ?
C33 C31 C32 111.9(2) . . ?
C12 C31 C32 110.0(2) . . ?
C40 C39 C38 119.3(3) . . ?
N1 C41 C40 121.3(3) . . ?
N1 C41 C42 117.7(2) . . ?
C40 C41 C42 121.0(3) . . ?
C39 C40 C41 119.7(3) . . ?
C4 C5 C6 120.5(2) . . ?
C16 C17 C18 121.6(3) . . ?
C13 C14 C15 118.0(3) . . ?
C13 C14 C25 121.1(3) . . ?
C15 C14 C25 120.9(3) . . ?
C5 C4 C3 119.4(2) . . ?
C27 C25 C26 112.5(4) . . ?
C27 C25 C14 113.0(3) . . ?
C26 C25 C14 113.4(3) . . ?
C16 C15 C14 122.4(3) . . ?
C18 C19 C21 111.9(3) . . ?
C18 C19 C20 112.3(3) . . ?
C21 C19 C20 110.7(3) . . ?
C15 C16 C17 118.4(3) . . ?
C15 C16 C22 120.4(4) . . ?
C17 C16 C22 121.2(4) . . ?
C35 C34 C10 115.2(4) . . ?
C35 C34 C36 114.7(4) . . ?
C10 C34 C36 110.6(3) . . ?
C24 C22 C23 127.6(4) . . ?
C24 C22 C16 117.3(4) . . ?
C23 C22 C16 114.5(3) . . ?
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
Cu1 C1 1.913(2) . ?
Cu1 N1 1.947(2) . ?
C1 C6 1.412(3) . ?
C1 C2 1.416(3) . ?
N1 C37 1.349(3) . ?
N1 C41 1.357(3) . ?
C8 C7 1.409(4) . ?
C8 C9 1.403(4) . ?
C8 C28 1.516(4) . ?
C6 C5 1.398(3) . ?
C6 C13 1.505(4) . ?
C13 C18 1.399(4) . ?
C13 C14 1.404(4) . ?
C2 C3 1.399(3) . ?
C2 C7 1.500(3) . ?
C3 C4 1.383(4) . ?
C7 C12 1.400(4) . ?
C9 C10 1.383(4) . ?
C12 C11 1.393(4) . ?
C12 C31 1.524(4) . ?
C37 C38 1.390(4) . ?
C37 C43 1.500(4) . ?
C28 C30 1.527(4) . ?
C28 C29 1.529(4) . ?
C18 C17 1.403(4) . ?
C18 C19 1.516(4) . ?
C11 C10 1.384(4) . ?
C10 C34 1.525(4) . ?
C38 C39 1.376(4) . ?
C31 C33 1.521(4) . ?
C31 C32 1.531(4) . ?
C39 C40 1.375(4) . ?
C41 C40 1.384(4) . ?
C41 C42 1.498(4) . ?
C5 C4 1.382(4) . ?
C17 C16 1.386(5) . ?
C14 C15 1.406(4) . ?
C14 C25 1.520(5) . ?
C25 C27 1.494(5) . ?
C25 C26 1.516(5) . ?
C15 C16 1.379(5) . ?
C19 C21 1.521(4) . ?
C19 C20 1.533(5) . ?
C24 C22 1.332(6) . ?
C16 C22 1.536(4) . ?
C34 C35 1.436(7) . ?
C34 C36 1.532(6) . ?
C22 C23 1.418(6) . ?
