#------------------------------------------------------------------------------
#$Date: 2016-03-25 15:45:19 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179934 $
#$URL: svn://www.crystallography.net/cod/cif/7/02/29/7022911.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_7022911
loop_
_publ_author_name
'Bai, Shi-Qiang'
'Jiang, Lu'
'Zuo, Jing-Lin'
'Hor, T. S. Andy'
_publ_section_title
;
 Hybrid NS ligands supported Cu(I)/(II) complexes for azide-alkyne
 cycloaddition reactions.
;
_journal_issue                   31
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11319
_journal_page_last               11326
_journal_paper_doi               10.1039/c3dt50247c
_journal_volume                  42
_journal_year                    2013
_chemical_formula_sum            'C30 H27 Cu2 I2 N9'
_chemical_formula_weight         894.49
_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                95.6190(10)
_cell_angle_beta                 90.2230(10)
_cell_angle_gamma                94.1080(10)
_cell_formula_units_Z            2
_cell_length_a                   10.1742(4)
_cell_length_b                   11.7158(5)
_cell_length_c                   13.8012(5)
_cell_measurement_reflns_used    7876
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.40
_cell_volume                     1632.88(11)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21424
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.48
_exptl_absorpt_coefficient_mu    3.228
_exptl_absorpt_correction_T_max  0.7384
_exptl_absorpt_correction_T_min  0.3064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.855
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7492
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0322
_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)+(0.0395P)²+0.9102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0819
_reflns_number_gt                6585
_reflns_number_total             7492
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3dt50247c.txt
_cod_data_source_block           P1
_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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7022911
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
Cu1 Cu 0.12246(4) 0.53378(4) 0.53922(3) 0.03016(10) Uani 1 1 d .
Cu2 Cu 0.62517(4) 0.53831(4) -0.03150(3) 0.02908(10) Uani 1 1 d .
I1 I -0.02105(2) 0.675867(18) 0.452402(15) 0.02940(7) Uani 1 1 d .
I2 I 0.47489(2) 0.672162(18) 0.076921(15) 0.02868(7) Uani 1 1 d .
N1 N 0.2901(2) 0.5223(2) 0.45590(18) 0.0246(5) Uani 1 1 d .
N2 N 0.7053(2) 0.4083(3) 0.27495(19) 0.0284(6) Uani 1 1 d .
N3 N 0.8084(3) 0.3816(2) 0.32830(19) 0.0282(6) Uani 1 1 d .
N4 N 0.8409(3) 0.2791(2) 0.29350(19) 0.0290(6) Uani 1 1 d .
N5 N 0.7916(2) 0.5275(2) 0.05388(18) 0.0248(6) Uani 1 1 d .
N6 N 1.2077(2) 0.4082(2) 0.21139(18) 0.0222(5) Uani 1 1 d .
N7 N 1.3044(3) 0.3763(2) 0.14949(18) 0.0242(5) Uani 1 1 d .
N8 N 1.3261(3) 0.2689(2) 0.16189(19) 0.0271(6) Uani 1 1 d .
C1 C 0.3463(3) 0.6173(3) 0.4211(2) 0.0277(7) Uani 1 1 d .
H1 H 0.3068 0.6863 0.4341 0.033 Uiso 1 1 calc R
C2 C 0.4594(3) 0.6169(3) 0.3671(2) 0.0291(7) Uani 1 1 d .
H2 H 0.4942 0.6844 0.3437 0.035 Uiso 1 1 calc R
C3 C 0.5218(3) 0.5157(3) 0.3476(2) 0.0260(7) Uani 1 1 d .
C4 C 0.4650(3) 0.4172(3) 0.3834(2) 0.0257(6) Uani 1 1 d .
H4 H 0.5034 0.3475 0.3719 0.031 Uiso 1 1 calc R
C5 C 0.3503(3) 0.4245(3) 0.4364(2) 0.0261(7) Uani 1 1 d .
H5 H 0.3128 0.3580 0.4599 0.031 Uiso 1 1 calc R
C6 C 0.6490(3) 0.5185(3) 0.2920(2) 0.0317(8) Uani 1 1 d .
H6A H 0.6335 0.5472 0.2297 0.038 Uiso 1 1 calc R
H6B H 0.7128 0.5724 0.3278 0.038 Uiso 1 1 calc R
C7 C 0.6704(3) 0.3217(3) 0.2067(2) 0.0334(8) Uani 1 1 d .
H7 H 0.6024 0.3183 0.1611 0.040 Uiso 1 1 calc R
C8 C 0.7566(3) 0.2396(3) 0.2189(2) 0.0296(7) Uani 1 1 d .
C9 C 0.7708(4) 0.1286(3) 0.1605(3) 0.0368(8) Uani 1 1 d .
C10 C 0.6683(5) 0.0763(4) 0.1027(4) 0.0696(15) Uani 1 1 d .
H10 H 0.5887 0.1105 0.1007 0.083 Uiso 1 1 calc R
C11 C 0.6839(8) -0.0259(5) 0.0483(5) 0.093(2) Uani 1 1 d .
H11 H 0.6144 -0.0596 0.0090 0.112 Uiso 1 1 calc R
C12 C 0.7971(7) -0.0791(4) 0.0499(4) 0.0812(19) Uani 1 1 d .
H12 H 0.8054 -0.1487 0.0127 0.097 Uiso 1 1 calc R
C13 C 0.8981(7) -0.0292(5) 0.1068(5) 0.0869(19) Uani 1 1 d .
H13 H 0.9769 -0.0648 0.1086 0.104 Uiso 1 1 calc R
C14 C 0.8850(5) 0.0742(4) 0.1622(4) 0.0701(15) Uani 1 1 d .
H14 H 0.9551 0.1072 0.2012 0.084 Uiso 1 1 calc R
C15 C 0.8542(3) 0.4301(3) 0.0529(2) 0.0259(7) Uani 1 1 d .
H15 H 0.8175 0.3644 0.0166 0.031 Uiso 1 1 calc R
C16 C 0.9706(3) 0.4232(3) 0.1035(2) 0.0228(6) Uani 1 1 d .
H16 H 1.0105 0.3540 0.1009 0.027 Uiso 1 1 calc R
C17 C 1.0270(3) 0.5193(3) 0.1579(2) 0.0218(6) Uani 1 1 d .
C18 C 0.9616(3) 0.6198(3) 0.1603(2) 0.0265(7) Uani 1 1 d .
H18 H 0.9958 0.6862 0.1970 0.032 Uiso 1 1 calc R
C19 C 0.8464(3) 0.6203(3) 0.1082(2) 0.0271(7) Uani 1 1 d .
H19 H 0.8041 0.6883 0.1107 0.032 Uiso 1 1 calc R
C20 C 1.1551(3) 0.5205(3) 0.2134(2) 0.0257(7) Uani 1 1 d .
H20A H 1.2197 0.5730 0.1861 0.031 Uiso 1 1 calc R
H20B H 1.1415 0.5495 0.2806 0.031 Uiso 1 1 calc R
C21 C 1.1671(3) 0.3213(3) 0.2629(2) 0.0259(7) Uani 1 1 d .
H21 H 1.1013 0.3210 0.3095 0.031 Uiso 1 1 calc R
C22 C 1.2430(3) 0.2328(3) 0.2322(2) 0.0257(7) Uani 1 1 d .
C23 C 1.2403(4) 0.1159(3) 0.2620(3) 0.0335(8) Uani 1 1 d .
C24 C 1.1570(5) 0.0836(4) 0.3355(3) 0.0529(11) Uani 1 1 d .
H24 H 1.1067 0.1376 0.3688 0.064 Uiso 1 1 calc R
C25 C 1.1488(6) -0.0286(4) 0.3594(4) 0.0718(15) Uani 1 1 d .
H25 H 1.0919 -0.0497 0.4082 0.086 Uiso 1 1 calc R
C26 C 1.2219(6) -0.1075(4) 0.3129(4) 0.0709(15) Uani 1 1 d .
H26 H 1.2144 -0.1831 0.3286 0.085 Uiso 1 1 calc R
C27 C 1.3049(7) -0.0772(5) 0.2442(5) 0.105(3) Uani 1 1 d .
H27 H 1.3568 -0.1315 0.2131 0.127 Uiso 1 1 calc R
C28 C 1.3153(6) 0.0355(4) 0.2182(4) 0.083(2) Uani 1 1 d .
H28 H 1.3743 0.0553 0.1703 0.100 Uiso 1 1 calc R
N1S N 0.5354(10) 0.1377(9) 0.4400(8) 0.181(4) Uani 1 1 d DU
C1S C 0.6072(13) 0.0756(11) 0.4117(9) 0.194(4) Uani 1 1 d D
C2S C 0.6763(13) -0.0274(9) 0.3836(8) 0.194(4) Uani 1 1 d D
H2S1 H 0.6555 -0.0836 0.4285 0.291 Uiso 1 1 calc R
H2S2 H 0.7696 -0.0079 0.3849 0.291 Uiso 1 1 calc R
H2S3 H 0.6492 -0.0584 0.3191 0.291 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'
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
N1 Cu1 N3 103.74(10) . 2_666
N1 Cu1 I1 106.73(8) . 2_566
N3 Cu1 I1 115.18(8) 2_666 2_566
N1 Cu1 I1 104.58(7) . .
N3 Cu1 I1 108.02(8) 2_666 .
I1 Cu1 I1 117.171(16) 2_566 .
N1 Cu1 Cu1 121.15(7) . 2_566
N3 Cu1 Cu1 134.73(8) 2_666 2_566
I1 Cu1 Cu1 59.464(16) 2_566 2_566
I1 Cu1 Cu1 57.707(16) . 2_566
N5 Cu2 N7 104.31(10) . 2_765
N5 Cu2 I2 106.84(8) . 2_665
N7 Cu2 I2 114.96(7) 2_765 2_665
N5 Cu2 I2 104.76(7) . .
N7 Cu2 I2 109.51(7) 2_765 .
I2 Cu2 I2 115.297(16) 2_665 .
N5 Cu2 Cu2 120.57(7) . 2_665
N7 Cu2 Cu2 134.92(7) 2_765 2_665
I2 Cu2 Cu2 57.961(15) 2_665 2_665
I2 Cu2 Cu2 57.336(15) . 2_665
Cu1 I1 Cu1 62.829(16) 2_566 .
Cu2 I2 Cu2 64.703(16) 2_665 .
C5 N1 C1 117.0(3) . .
C5 N1 Cu1 123.4(2) . .
C1 N1 Cu1 119.5(2) . .
C7 N2 N3 110.4(3) . .
C7 N2 C6 128.0(3) . .
N3 N2 C6 121.6(3) . .
N4 N3 N2 107.6(2) . .
N4 N3 Cu1 124.1(2) . 2_666
N2 N3 Cu1 126.8(2) . 2_666
N3 N4 C8 108.3(3) . .
C19 N5 C15 116.9(3) . .
C19 N5 Cu2 121.0(2) . .
C15 N5 Cu2 122.0(2) . .
C21 N6 N7 110.5(2) . .
C21 N6 C20 127.5(3) . .
N7 N6 C20 121.9(2) . .
N8 N7 N6 107.5(2) . .
N8 N7 Cu2 124.0(2) . 2_765
N6 N7 Cu2 126.87(19) . 2_765
N7 N8 C22 108.3(3) . .
N1 C1 C2 122.9(3) . .
C1 C2 C3 119.9(3) . .
C2 C3 C4 117.7(3) . .
C2 C3 C6 119.0(3) . .
C4 C3 C6 123.3(3) . .
C5 C4 C3 118.8(3) . .
N1 C5 C4 123.6(3) . .
N2 C6 C3 114.5(3) . .
N2 C7 C8 105.0(3) . .
N4 C8 C7 108.6(3) . .
N4 C8 C9 121.9(3) . .
C7 C8 C9 129.3(3) . .
C14 C9 C10 117.9(4) . .
C14 C9 C8 121.3(3) . .
C10 C9 C8 120.8(4) . .
C11 C10 C9 119.9(5) . .
C12 C11 C10 122.0(5) . .
C11 C12 C13 118.8(5) . .
C12 C13 C14 120.4(6) . .
C9 C14 C13 121.1(5) . .
N5 C15 C16 123.0(3) . .
C17 C16 C15 119.7(3) . .
C16 C17 C18 117.5(3) . .
C16 C17 C20 123.4(3) . .
C18 C17 C20 119.1(3) . .
C19 C18 C17 119.6(3) . .
N5 C19 C18 123.3(3) . .
N6 C20 C17 113.6(3) . .
N6 C21 C22 105.4(3) . .
N8 C22 C21 108.3(3) . .
N8 C22 C23 122.1(3) . .
C21 C22 C23 129.6(3) . .
C28 C23 C24 117.8(4) . .
C28 C23 C22 122.0(4) . .
C24 C23 C22 120.2(3) . .
C25 C24 C23 120.1(4) . .
C26 C25 C24 120.8(5) . .
C27 C26 C25 119.7(5) . .
C26 C27 C28 120.8(5) . .
C23 C28 C27 120.7(5) . .
N1S C1S C2S 165.2(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.066(3) .
Cu1 N3 2.087(3) 2_666
Cu1 I1 2.6085(5) 2_566
Cu1 I1 2.6578(5) .
Cu1 Cu1 2.7452(8) 2_566
Cu2 N5 2.078(3) .
Cu2 N7 2.096(3) 2_765
Cu2 I2 2.6158(5) 2_665
Cu2 I2 2.6340(5) .
Cu2 Cu2 2.8093(8) 2_665
I1 Cu1 2.6085(5) 2_566
I2 Cu2 2.6158(5) 2_665
N1 C5 1.341(4) .
N1 C1 1.347(4) .
N2 C7 1.341(4) .
N2 N3 1.351(4) .
N2 C6 1.449(4) .
N3 N4 1.315(4) .
N3 Cu1 2.087(3) 2_666
N4 C8 1.361(4) .
N5 C19 1.344(4) .
N5 C15 1.344(4) .
N6 C21 1.340(4) .
N6 N7 1.354(3) .
N6 C20 1.453(4) .
N7 N8 1.320(4) .
N7 Cu2 2.096(3) 2_765
N8 C22 1.368(4) .
C1 C2 1.373(4) .
C2 C3 1.388(5) .
C3 C4 1.389(5) .
C3 C6 1.507(4) .
C4 C5 1.383(4) .
C7 C8 1.369(5) .
C8 C9 1.478(5) .
C9 C14 1.366(6) .
C9 C10 1.380(6) .
C10 C11 1.369(8) .
C11 C12 1.349(9) .
C12 C13 1.354(8) .
C13 C14 1.383(7) .
C15 C16 1.384(4) .
C16 C17 1.378(4) .
C17 C18 1.391(4) .
C17 C20 1.508(4) .
C18 C19 1.374(4) .
C21 C22 1.372(4) .
C22 C23 1.467(5) .
C23 C28 1.352(6) .
C23 C24 1.388(5) .
C24 C25 1.383(6) .
C25 C26 1.345(7) .
C26 C27 1.329(7) .
C27 C28 1.398(7) .
N1S C1S 1.113(5) .
C1S C2S 1.460(5) .
