#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:13:32 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179051 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/13/4301307.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_4301307
loop_
_publ_author_name
'Shi-Qiang Bai'
'Lip Lin Koh'
'T. S. Andy Hor'
_publ_contact_author_address
;
Department of Chemistry, National University of Singapore,
Kent Ridge, Singapore 117543
;
_publ_contact_author_email       andyhor@nus.edu.sg
_publ_contact_author_fax         65-6873-1324
_publ_contact_author_name        'Prof. T. S. Andy Hor'
_publ_contact_author_phone       65-6516-2663
_publ_section_title
;
Structures of Copper Complexes of the Hybrid [SNS] Ligand of
Bis(2-(benzylthio)ethyl)amine and Facile Catalytic Formation of
1-Benzyl-4-phenyl-1H-1,2,3-triazole through Click Reaction
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1207
_journal_page_last               1213
_journal_paper_doi               10.1021/ic801690v
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C18 H23 Cu2 I2 N S2'
_chemical_formula_weight         698.37
_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                93.3430(10)
_cell_angle_beta                 100.8220(10)
_cell_angle_gamma                105.4800(10)
_cell_formula_units_Z            2
_cell_length_a                   9.1552(6)
_cell_length_b                   10.7244(7)
_cell_length_c                   12.2586(8)
_cell_measurement_reflns_used    4815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.98
_cell_measurement_theta_min      2.36
_cell_volume                     1131.81(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14980
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    4.793
_exptl_absorpt_correction_T_max  0.8314
_exptl_absorpt_correction_T_min  0.2773
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Plate
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.411
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constructed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5182
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+1.4750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1182
_reflns_number_gt                4419
_reflns_number_total             5182
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801690v_si_001_1.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4301307
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 0.64164(9) 0.05829(7) 0.53769(6) 0.0537(2) Uani 1 1 d . . .
I1 I 0.58783(4) -0.16041(3) 0.41586(3) 0.04869(13) Uani 1 1 d . . .
Cu2 Cu 0.49553(9) 0.36792(7) 0.47394(6) 0.05205(19) Uani 1 1 d . . .
I2 I 0.74205(4) 0.53924(3) 0.59711(4) 0.05216(13) Uani 1 1 d . . .
S1 S 0.7984(2) 0.06859(19) 0.71081(14) 0.0629(4) Uani 1 1 d . . .
N1 N 0.7958(5) 0.2245(4) 0.5016(4) 0.0450(10) Uani 1 1 d D . .
H1N H 0.763(7) 0.285(5) 0.535(5) 0.060 Uiso 1 1 d D . .
C1 C 0.9451(8) 0.2444(7) 0.5800(7) 0.0686(19) Uani 1 1 d . . .
H1A H 1.0105 0.3316 0.5787 0.082 Uiso 1 1 calc R . .
H1B H 0.9971 0.1831 0.5561 0.082 Uiso 1 1 calc R . .
C2 C 0.9249(9) 0.2265(7) 0.6963(6) 0.075(2) Uani 1 1 d . . .
H2A H 0.8828 0.2939 0.7224 0.090 Uiso 1 1 calc R . .
H2B H 1.0258 0.2380 0.7441 0.090 Uiso 1 1 calc R . .
C3 C 0.9162(9) -0.0406(7) 0.6920(5) 0.0637(17) Uani 1 1 d . . .
H3A H 0.8482 -0.1262 0.6611 0.076 Uiso 1 1 calc R . .
H3B H 0.9790 -0.0089 0.6385 0.076 Uiso 1 1 calc R . .
C4 C 1.0204(7) -0.0525(6) 0.7984(5) 0.0521(14) Uani 1 1 d . . .
C5 C 1.1708(9) 0.0228(7) 0.8267(6) 0.0670(18) Uani 1 1 d . . .
H5 H 1.2079 0.0850 0.7812 0.080 Uiso 1 1 calc R . .
C6 C 1.2702(10) 0.0069(10) 0.9240(7) 0.084(2) Uani 1 1 d . . .
H6 H 1.3731 0.0573 0.9423 0.101 Uiso 1 1 calc R . .
C7 C 1.2158(13) -0.0810(11) 0.9900(7) 0.093(3) Uani 1 1 d . . .
H7 H 1.2816 -0.0911 1.0544 0.112 Uiso 1 1 calc R . .
C8 C 1.0656(14) -0.1560(11) 0.9647(8) 0.104(3) Uani 1 1 d . . .
H8 H 1.0294 -0.2161 1.0121 0.124 Uiso 1 1 calc R . .
C9 C 0.9660(10) -0.1428(8) 0.8675(7) 0.083(2) Uani 1 1 d . . .
H9 H 0.8637 -0.1946 0.8496 0.099 Uiso 1 1 calc R . .
S2 S 0.5324(2) 0.29283(16) 0.30161(13) 0.0531(4) Uani 1 1 d . . .
C11 C 0.6669(8) 0.1964(6) 0.3009(5) 0.0598(17) Uani 1 1 d . . .
H11A H 0.6139 0.1079 0.3106 0.072 Uiso 1 1 calc R . .
H11B H 0.6919 0.1943 0.2275 0.072 Uiso 1 1 calc R . .
C12 C 0.6271(11) 0.4364(7) 0.2463(6) 0.074(2) Uani 1 1 d . . .
H12A H 0.5710 0.5006 0.2523 0.089 Uiso 1 1 calc R . .
H12B H 0.7309 0.4725 0.2917 0.089 Uiso 1 1 calc R . .
C10 C 0.8151(8) 0.2386(7) 0.3855(6) 0.0662(18) Uani 1 1 d . . .
H10A H 0.8826 0.1879 0.3680 0.079 Uiso 1 1 calc R . .
H10B H 0.8658 0.3293 0.3804 0.079 Uiso 1 1 calc R . .
C13 C 0.6386(10) 0.4129(7) 0.1251(6) 0.0674(18) Uani 1 1 d . . .
C14 C 0.5098(11) 0.3454(8) 0.0424(7) 0.082(2) Uani 1 1 d . . .
H14 H 0.4151 0.3093 0.0616 0.099 Uiso 1 1 calc R . .
C15 C 0.5227(13) 0.3322(9) -0.0685(7) 0.093(3) Uani 1 1 d . . .
H15 H 0.4370 0.2873 -0.1235 0.111 Uiso 1 1 calc R . .
C16 C 0.6615(16) 0.3852(12) -0.0961(9) 0.109(4) Uani 1 1 d . . .
H16 H 0.6713 0.3752 -0.1701 0.130 Uiso 1 1 calc R . .
C17 C 0.7813(13) 0.4501(14) -0.0188(10) 0.125(4) Uani 1 1 d . . .
H17 H 0.8739 0.4907 -0.0391 0.150 Uiso 1 1 calc R . .
C18 C 0.7726(11) 0.4594(11) 0.0925(8) 0.103(3) Uani 1 1 d . . .
H18 H 0.8621 0.4990 0.1462 0.124 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'
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'
I I -0.4742 1.8119 '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
N1 Cu1 S1 91.20(15) . . ?
N1 Cu1 Cu1 134.38(14) . 2_656 ?
S1 Cu1 Cu1 131.02(7) . 2_656 ?
N1 Cu1 I1 119.44(13) . . ?
S1 Cu1 I1 112.96(5) . . ?
Cu1 Cu1 I1 65.03(3) 2_656 . ?
N1 Cu1 I1 100.41(12) . 2_656 ?
S1 Cu1 I1 103.68(5) . 2_656 ?
Cu1 Cu1 I1 58.50(3) 2_656 2_656 ?
I1 Cu1 I1 123.53(3) . 2_656 ?
Cu1 I1 Cu2 113.02(3) . 2_656 ?
Cu1 I1 Cu1 56.47(3) . 2_656 ?
Cu2 I1 Cu1 93.79(2) 2_656 2_656 ?
S2 Cu2 I2 113.94(5) . . ?
S2 Cu2 I2 99.10(5) . 2_666 ?
I2 Cu2 I2 114.88(3) . 2_666 ?
S2 Cu2 I1 107.51(5) . 2_656 ?
I2 Cu2 I1 109.54(3) . 2_656 ?
I2 Cu2 I1 111.33(3) 2_666 2_656 ?
S2 Cu2 Cu2 121.55(6) . 2_666 ?
I2 Cu2 Cu2 57.75(3) . 2_666 ?
I2 Cu2 Cu2 57.14(3) 2_666 2_666 ?
I1 Cu2 Cu2 130.45(4) 2_656 2_666 ?
Cu2 I2 Cu2 65.12(3) . 2_666 ?
C2 S1 C3 102.6(4) . . ?
C2 S1 Cu1 92.3(2) . . ?
C3 S1 Cu1 105.5(2) . . ?
C1 N1 C10 112.1(5) . . ?
C1 N1 Cu1 107.4(4) . . ?
C10 N1 Cu1 120.2(4) . . ?
N1 C1 C2 111.9(6) . . ?
C1 C2 S1 114.2(5) . . ?
C4 C3 S1 113.2(4) . . ?
C5 C4 C9 119.2(7) . . ?
C5 C4 C3 120.8(6) . . ?
C9 C4 C3 120.0(7) . . ?
C4 C5 C6 120.5(7) . . ?
C7 C6 C5 119.5(9) . . ?
C6 C7 C8 121.2(8) . . ?
C7 C8 C9 120.0(8) . . ?
C4 C9 C8 119.5(8) . . ?
C12 S2 C11 101.8(3) . . ?
C12 S2 Cu2 104.9(2) . . ?
C11 S2 Cu2 118.1(2) . . ?
C10 C11 S2 117.6(5) . . ?
C13 C12 S2 113.9(5) . . ?
N1 C10 C11 113.8(5) . . ?
C18 C13 C14 117.0(8) . . ?
C18 C13 C12 121.1(8) . . ?
C14 C13 C12 121.8(8) . . ?
C15 C14 C13 120.2(9) . . ?
C16 C15 C14 119.7(10) . . ?
C17 C16 C15 120.0(10) . . ?
C16 C17 C18 121.1(11) . . ?
C13 C18 C17 121.8(10) . . ?
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 N1 2.085(5) . ?
Cu1 S1 2.3065(18) . ?
Cu1 Cu1 2.5254(15) 2_656 ?
Cu1 I1 2.5831(9) . ?
Cu1 I1 2.7463(9) 2_656 ?
I1 Cu2 2.6817(8) 2_656 ?
I1 Cu1 2.7463(9) 2_656 ?
Cu2 S2 2.3322(17) . ?
Cu2 I2 2.6329(9) . ?
Cu2 I2 2.6509(8) 2_666 ?
Cu2 I1 2.6816(8) 2_656 ?
Cu2 Cu2 2.8436(15) 2_666 ?
I2 Cu2 2.6509(8) 2_666 ?
S1 C2 1.818(8) . ?
S1 C3 1.823(6) . ?
N1 C1 1.471(8) . ?
N1 C10 1.478(8) . ?
C1 C2 1.488(11) . ?
C3 C4 1.498(9) . ?
C4 C5 1.364(10) . ?
C4 C9 1.379(10) . ?
C5 C6 1.407(11) . ?
C6 C7 1.334(13) . ?
C7 C8 1.361(15) . ?
C8 C9 1.397(12) . ?
S2 C12 1.792(7) . ?
S2 C11 1.808(6) . ?
C11 C10 1.487(10) . ?
C12 C13 1.520(10) . ?
C13 C18 1.339(12) . ?
C13 C14 1.398(12) . ?
C14 C15 1.388(11) . ?
C15 C16 1.361(15) . ?
C16 C17 1.308(15) . ?
C17 C18 1.381(14) . ?
