#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:13:32 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179051 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/13/4301310.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_4301310
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            'C20 H25 Cu F6 N O7 S4'
_chemical_formula_weight         697.19
_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                104.804(2)
_cell_angle_beta                 91.809(2)
_cell_angle_gamma                105.428(2)
_cell_formula_units_Z            2
_cell_length_a                   8.3046(8)
_cell_length_b                   11.4671(11)
_cell_length_c                   16.2159(15)
_cell_measurement_reflns_used    4876
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.56
_cell_volume                     1430.9(2)
_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      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18481
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    1.133
_exptl_absorpt_correction_T_max  0.8951
_exptl_absorpt_correction_T_min  0.5495
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sababs, (Sheldrick 2001)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             710
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         6559
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0477
_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)+(0.0829P)²+0.0276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1263
_refine_ls_wR_factor_ref         0.1378
_reflns_number_gt                4684
_reflns_number_total             6559
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic801690v_si_001_4.cif
_cod_data_source_block           3
_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               4301310
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 0.26344(4) 0.24517(3) 0.18633(2) 0.03972(13) Uani 1 1 d . . .
S1 S 0.12306(9) 0.05977(7) 0.22176(5) 0.04588(19) Uani 1 1 d . . .
S2 S 0.34307(10) 0.43535(7) 0.14537(5) 0.0475(2) Uani 1 1 d . . .
N1 N 0.1476(3) 0.3311(2) 0.27683(15) 0.0377(5) Uani 1 1 d D . .
H1N H 0.049(3) 0.318(3) 0.2522(18) 0.050 Uiso 1 1 d D . .
O1 O 0.3700(3) 0.1585(2) 0.09573(16) 0.0606(6) Uani 1 1 d D . .
H1A H 0.318(4) 0.082(2) 0.066(2) 0.080 Uiso 1 1 d D . .
H1B H 0.451(4) 0.138(4) 0.118(2) 0.080 Uiso 1 1 d D . .
C1 C 0.1369(4) 0.2752(3) 0.3496(2) 0.0495(7) Uani 1 1 d . . .
H1C H 0.0771 0.3166 0.3928 0.059 Uiso 1 1 calc R . .
H1D H 0.2489 0.2864 0.3754 0.059 Uiso 1 1 calc R . .
C2 C 0.0458(4) 0.1375(3) 0.3176(2) 0.0556(8) Uani 1 1 d . . .
H2A H -0.0730 0.1275 0.3055 0.067 Uiso 1 1 calc R . .
H2B H 0.0582 0.0973 0.3623 0.067 Uiso 1 1 calc R . .
C3 C 0.2187(4) 0.4685(3) 0.3016(2) 0.0471(7) Uani 1 1 d . . .
H3A H 0.3308 0.4916 0.3311 0.057 Uiso 1 1 calc R . .
H3B H 0.1494 0.5077 0.3402 0.057 Uiso 1 1 calc R . .
C4 C 0.2256(4) 0.5131(3) 0.2218(2) 0.0505(7) Uani 1 1 d . . .
H4A H 0.2777 0.6032 0.2372 0.061 Uiso 1 1 calc R . .
H4B H 0.1122 0.4966 0.1957 0.061 Uiso 1 1 calc R . .
C5 C 0.2847(4) 0.0033(3) 0.2637(3) 0.0604(9) Uani 1 1 d . . .
H5A H 0.3288 -0.0451 0.2163 0.072 Uiso 1 1 calc R . .
H5B H 0.3763 0.0746 0.2953 0.072 Uiso 1 1 calc R . .
C6 C 0.2167(4) -0.0772(3) 0.3215(2) 0.0572(8) Uani 1 1 d . . .
C7 C 0.0870(5) -0.1853(3) 0.2927(3) 0.0674(10) Uani 1 1 d . . .
H7 H 0.0412 -0.2089 0.2358 0.081 Uiso 1 1 calc R . .
C8 C 0.0223(6) -0.2596(4) 0.3439(4) 0.0891(14) Uani 1 1 d . . .
H8 H -0.0661 -0.3323 0.3223 0.107 Uiso 1 1 calc R . .
C9 C 0.0866(9) -0.2274(7) 0.4245(5) 0.121(2) Uani 1 1 d . . .
H9 H 0.0418 -0.2783 0.4594 0.145 Uiso 1 1 calc R . .
C10 C 0.2194(10) -0.1197(8) 0.4592(4) 0.134(2) Uani 1 1 d . . .
H10 H 0.2645 -0.0989 0.5160 0.161 Uiso 1 1 calc R . .
C11 C 0.2834(6) -0.0431(5) 0.4051(3) 0.0999(15) Uani 1 1 d . . .
H11 H 0.3706 0.0304 0.4265 0.120 Uiso 1 1 calc R . .
C12 C 0.5596(4) 0.5190(3) 0.1932(2) 0.0548(8) Uani 1 1 d . . .
H12A H 0.5711 0.5167 0.2524 0.066 Uiso 1 1 calc R . .
H12B H 0.6360 0.4771 0.1625 0.066 Uiso 1 1 calc R . .
C13 C 0.6052(3) 0.6525(3) 0.1897(2) 0.0468(7) Uani 1 1 d . . .
C14 C 0.5998(4) 0.7484(3) 0.2605(3) 0.0666(10) Uani 1 1 d . . .
H14 H 0.5718 0.7299 0.3117 0.080 Uiso 1 1 calc R . .
C15 C 0.6357(5) 0.8719(4) 0.2561(4) 0.0828(13) Uani 1 1 d . . .
H15 H 0.6300 0.9355 0.3038 0.099 Uiso 1 1 calc R . .
C16 C 0.6787(5) 0.8987(4) 0.1825(4) 0.0956(17) Uani 1 1 d . . .
H16 H 0.7011 0.9812 0.1792 0.115 Uiso 1 1 calc R . .
C17 C 0.6897(6) 0.8071(5) 0.1131(4) 0.1009(17) Uani 1 1 d . . .
H17 H 0.7230 0.8276 0.0631 0.121 Uiso 1 1 calc R . .
C18 C 0.6519(5) 0.6834(4) 0.1157(3) 0.0742(11) Uani 1 1 d . . .
H18 H 0.6581 0.6209 0.0674 0.089 Uiso 1 1 calc R . .
S3 S 0.67561(8) 0.31441(7) 0.32419(5) 0.04233(19) Uani 1 1 d . . .
O2 O 0.5108(2) 0.3049(2) 0.28723(14) 0.0518(5) Uani 1 1 d . . .
O3 O 0.6939(3) 0.2003(2) 0.33802(18) 0.0712(7) Uani 1 1 d . . .
O4 O 0.8119(3) 0.3852(3) 0.28956(16) 0.0668(7) Uani 1 1 d . . .
C19 C 0.6838(4) 0.4144(4) 0.4309(2) 0.0653(10) Uani 1 1 d . . .
F1 F 0.5703(4) 0.3613(3) 0.47525(17) 0.1112(10) Uani 1 1 d . . .
F2 F 0.6597(4) 0.5234(2) 0.42871(18) 0.1046(9) Uani 1 1 d . . .
F3 F 0.8328(3) 0.4394(3) 0.47438(16) 0.1056(9) Uani 1 1 d . . .
S4 S -0.16774(10) 0.18174(8) 0.04753(5) 0.0529(2) Uani 1 1 d . . .
O5 O -0.1959(5) 0.0759(3) -0.0243(2) 0.1190(13) Uani 1 1 d . . .
O6 O -0.3014(4) 0.1819(5) 0.0977(3) 0.1336(15) Uani 1 1 d . . .
O7 O -0.0130(4) 0.2177(3) 0.0974(2) 0.0964(10) Uani 1 1 d . . .
C20 C -0.1553(7) 0.3081(5) -0.0013(4) 0.0914(14) Uani 1 1 d . . .
F4 F -0.2859(6) 0.2911(5) -0.0484(4) 0.237(3) Uani 1 1 d . . .
F5 F -0.1272(6) 0.4156(3) 0.0588(3) 0.1603(16) Uani 1 1 d . . .
F6 F -0.0332(6) 0.3217(4) -0.0463(3) 0.1755(18) 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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N1 178.21(10) . . ?
O1 Cu1 S1 93.67(8) . . ?
N1 Cu1 S1 85.64(7) . . ?
O1 Cu1 S2 93.09(8) . . ?
N1 Cu1 S2 87.28(7) . . ?
S1 Cu1 S2 167.16(3) . . ?
O1 Cu1 O2 92.01(9) . . ?
N1 Cu1 O2 89.72(8) . . ?
S1 Cu1 O2 97.33(5) . . ?
S2 Cu1 O2 93.33(5) . . ?
C2 S1 C5 103.34(17) . . ?
C2 S1 Cu1 95.94(11) . . ?
C5 S1 Cu1 106.60(11) . . ?
C4 S2 C12 101.18(15) . . ?
C4 S2 Cu1 94.00(11) . . ?
C12 S2 Cu1 107.45(11) . . ?
C3 N1 C1 114.0(2) . . ?
C3 N1 Cu1 112.60(17) . . ?
C1 N1 Cu1 110.65(17) . . ?
N1 C1 C2 109.0(3) . . ?
C1 C2 S1 112.6(2) . . ?
N1 C3 C4 108.6(2) . . ?
C3 C4 S2 111.4(2) . . ?
C6 C5 S1 111.5(2) . . ?
C11 C6 C7 118.4(4) . . ?
C11 C6 C5 120.1(4) . . ?
C7 C6 C5 121.5(3) . . ?
C8 C7 C6 122.7(4) . . ?
C9 C8 C7 119.1(5) . . ?
C8 C9 C10 122.2(5) . . ?
C9 C10 C11 117.7(5) . . ?
C6 C11 C10 119.8(5) . . ?
C13 C12 S2 111.0(2) . . ?
C18 C13 C14 118.2(3) . . ?
C18 C13 C12 120.8(3) . . ?
C14 C13 C12 121.0(3) . . ?
C13 C14 C15 120.9(4) . . ?
C16 C15 C14 119.5(4) . . ?
C15 C16 C17 120.8(4) . . ?
C16 C17 C18 120.7(4) . . ?
C13 C18 C17 120.0(4) . . ?
O3 S3 O4 116.03(15) . . ?
O3 S3 O2 114.48(14) . . ?
O4 S3 O2 114.89(14) . . ?
O3 S3 C19 103.93(18) . . ?
O4 S3 C19 102.99(17) . . ?
O2 S3 C19 101.90(14) . . ?
S3 O2 Cu1 161.23(14) . . ?
F1 C19 F2 108.2(3) . . ?
F1 C19 F3 107.0(3) . . ?
F2 C19 F3 107.4(3) . . ?
F1 C19 S3 112.0(3) . . ?
F2 C19 S3 111.2(3) . . ?
F3 C19 S3 110.8(2) . . ?
O6 S4 O7 112.2(2) . . ?
O6 S4 O5 114.9(3) . . ?
O7 S4 O5 116.3(2) . . ?
O6 S4 C20 105.2(3) . . ?
O7 S4 C20 103.8(2) . . ?
O5 S4 C20 102.6(2) . . ?
F4 C20 F6 107.7(6) . . ?
F4 C20 F5 109.2(5) . . ?
F6 C20 F5 105.9(5) . . ?
F4 C20 S4 112.3(4) . . ?
F6 C20 S4 111.7(4) . . ?
F5 C20 S4 109.9(4) . . ?
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 O1 1.932(2) . ?
Cu1 N1 1.976(2) . ?
Cu1 S1 2.3573(8) . ?
Cu1 S2 2.3738(8) . ?
Cu1 O2 2.415(2) . ?
S1 C2 1.812(3) . ?
S1 C5 1.820(3) . ?
S2 C4 1.805(3) . ?
S2 C12 1.835(3) . ?
N1 C3 1.469(4) . ?
N1 C1 1.474(4) . ?
C1 C2 1.502(5) . ?
C3 C4 1.505(5) . ?
C5 C6 1.500(5) . ?
C6 C11 1.365(6) . ?
C6 C7 1.370(5) . ?
C7 C8 1.360(5) . ?
C8 C9 1.316(8) . ?
C9 C10 1.393(9) . ?
C10 C11 1.413(8) . ?
C12 C13 1.492(4) . ?
C13 C18 1.375(5) . ?
C13 C14 1.383(5) . ?
C14 C15 1.389(6) . ?
C15 C16 1.343(7) . ?
C16 C17 1.354(7) . ?
C17 C18 1.381(6) . ?
S3 O3 1.427(2) . ?
S3 O4 1.428(2) . ?
S3 O2 1.4422(19) . ?
S3 C19 1.803(4) . ?
C19 F1 1.318(5) . ?
C19 F2 1.326(5) . ?
C19 F3 1.328(4) . ?
S4 O6 1.397(3) . ?
S4 O7 1.399(3) . ?
S4 O5 1.411(3) . ?
S4 C20 1.802(5) . ?
C20 F4 1.248(6) . ?
C20 F6 1.268(6) . ?
C20 F5 1.320(6) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O7 0.856(17) 2.45(3) 2.972(4) 120(2) .
O1 H1A O5 0.873(19) 1.76(2) 2.625(4) 168(4) 2
O1 H1B O6 0.870(18) 2.04(4) 2.668(4) 128(4) 1_655
