#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/39/7053993.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_7053993
loop_
_publ_author_name
'Benkhellat, Zakia'
'Allali, Mustapha'
'Beley, Marc'
'Wenger, Emmanuel'
'Bernard, Maxime'
'Parizel, Nathalie'
'Selmeczi, Katalin'
'Joly, Jean-Pierre'
_publ_section_title
;
 Click synthesis of symmetric bis-triazol ligands and full
 characterisation of their copper(ii)-complexes
;
_journal_issue                   1
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              419
_journal_paper_doi               10.1039/c3nj00570d
_journal_volume                  38
_journal_year                    2014
_chemical_formula_moiety         'C30 H40 Cu N8 O4, 2(Cl O4)'
_chemical_formula_sum            'C30 H40 Cl2 Cu N8 O12'
_chemical_formula_weight         839.15
_chemical_name_common            '[CuL2](ClO4)2'
_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
_audit_update_record
;
2013-09-02 # Formatted by publCIF

;
_cell_angle_alpha                101.979(4)
_cell_angle_beta                 108.296(5)
_cell_angle_gamma                106.798(5)
_cell_formula_units_Z            1
_cell_length_a                   9.390(5)
_cell_length_b                   10.293(5)
_cell_length_c                   10.426(5)
_cell_measurement_reflns_used    21737
_cell_measurement_temperature    110.0(1)
_cell_measurement_theta_max      33.0227
_cell_measurement_theta_min      3.2106
_cell_volume                     865.2(8)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      110.0(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            41373
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         3.2106
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             435
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         4169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0249
_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)+(0.0336P)²+0.5393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0678
_reflns_number_gt                3866
_reflns_number_total             4169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00570d.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        865.2(7)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7053993
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
H1A H 0.232(2) -0.1918(18) 0.2243(18) 0.011(4) Uiso 1 1 d .
H1B H 0.260(2) -0.1591(17) 0.0942(18) 0.012(4) Uiso 1 1 d .
Cu1 Cu 0.0000 0.0000 0.0000 0.00922(7) Uani 1 2 d S
O3 O -0.07440(12) -0.35319(10) 0.10291(10) 0.01497(19) Uani 1 1 d .
O1 O -0.25873(11) -0.21782(10) -0.08204(10) 0.01426(19) Uani 1 1 d .
N1 N 0.06139(13) -0.08882(11) -0.15508(11) 0.0112(2) Uani 1 1 d .
N2 N -0.15101(13) 0.03922(11) -0.17093(11) 0.0102(2) Uani 1 1 d .
N5 N 0.13484(13) -0.17954(12) -0.17033(12) 0.0122(2) Uani 1 1 d .
N6 N 0.11783(13) -0.21246(12) -0.30654(11) 0.0110(2) Uani 1 1 d .
C1 C 0.18182(16) -0.17434(14) 0.13557(14) 0.0124(2) Uani 1 1 d .
C2 C 0.03317(16) -0.30634(14) 0.03559(14) 0.0140(2) Uani 1 1 d .
H2A H -0.0241 -0.2852 -0.0475 0.017 Uiso 1 1 calc R
H2B H 0.0667 -0.3833 0.0031 0.017 Uiso 1 1 calc R
C3 C -0.24076(17) -0.41612(15) 0.00496(16) 0.0181(3) Uani 1 1 d .
H3A H -0.3003 -0.4881 0.0361 0.022 Uiso 1 1 calc R
H3B H -0.2478 -0.4644 -0.0885 0.022 Uiso 1 1 calc R
C4 C -0.31999(17) -0.30863(16) -0.00826(16) 0.0191(3) Uani 1 1 d .
H4A H -0.4364 -0.3591 -0.0600 0.023 Uiso 1 1 calc R
H4B H -0.2995 -0.2500 0.0864 0.023 Uiso 1 1 calc R
C5 C -0.36508(15) -0.14805(15) -0.13636(15) 0.0146(3) Uani 1 1 d .
H5A H -0.3578 -0.0721 -0.0588 0.018 Uiso 1 1 calc R
H5B H -0.4765 -0.2166 -0.1842 0.018 Uiso 1 1 calc R
C6 C -0.31187(15) -0.08661(14) -0.24023(14) 0.0130(2) Uani 1 1 d .
H6A H -0.3942 -0.0563 -0.2930 0.016 Uiso 1 1 calc R
H6B H -0.3045 -0.1617 -0.3084 0.016 Uiso 1 1 calc R
C7 C -0.07916(16) 0.04111(14) -0.28048(13) 0.0117(2) Uani 1 1 d .
H7A H -0.1635 0.0156 -0.3744 0.014 Uiso 1 1 calc R
H7B H -0.0003 0.1365 -0.2577 0.014 Uiso 1 1 calc R
C8 C 0.00039(15) -0.06411(13) -0.27983(13) 0.0108(2) Uani 1 1 d .
C9 C 0.03536(15) -0.14415(14) -0.37868(14) 0.0118(2) Uani 1 1 d .
H9 H 0.0085 -0.1503 -0.4741 0.014 Uiso 1 1 calc R
C10 C 0.18292(15) -0.31125(14) -0.36021(14) 0.0117(2) Uani 1 1 d .
C11 C 0.17524(16) -0.42869(14) -0.31240(15) 0.0152(3) Uani 1 1 d .
H11 H 0.1281 -0.4434 -0.2477 0.018 Uiso 1 1 calc R
C12 C 0.23949(18) -0.52322(15) -0.36345(16) 0.0193(3) Uani 1 1 d .
H12 H 0.2378 -0.6012 -0.3313 0.023 Uiso 1 1 calc R
C13 C 0.30642(18) -0.50197(16) -0.46258(17) 0.0218(3) Uani 1 1 d .
H13 H 0.3480 -0.5666 -0.4973 0.026 Uiso 1 1 calc R
C15 C 0.25100(16) -0.28709(15) -0.45742(15) 0.0157(3) Uani 1 1 d .
H15 H 0.2561 -0.2071 -0.4868 0.019 Uiso 1 1 calc R
C14 C 0.31164(18) -0.38465(16) -0.51020(16) 0.0200(3) Uani 1 1 d .
H14 H 0.3556 -0.3715 -0.5772 0.024 Uiso 1 1 calc R
Cl1 Cl 0.40218(4) 0.15437(3) 0.69192(3) 0.01240(8) Uani 1 1 d .
O21 O 0.40901(13) 0.07327(12) 0.78925(12) 0.0217(2) Uani 1 1 d .
O22 O 0.44256(14) 0.09080(13) 0.57860(11) 0.0253(2) Uani 1 1 d .
O23 O 0.51392(13) 0.30053(11) 0.76665(13) 0.0258(2) Uani 1 1 d .
O24 O 0.23934(12) 0.15174(11) 0.63127(11) 0.0187(2) 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'
Cl Cl 0.1484 0.1585 '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
N1 Cu1 N1 180.00(5) . 2
N1 Cu1 N2 81.10(6) . .
N1 Cu1 N2 98.90(6) 2 .
N1 Cu1 N2 98.90(6) . 2
N1 Cu1 N2 81.10(6) 2 2
N2 Cu1 N2 180.00(6) . 2
C3 O3 C2 112.39(11) . .
C4 O1 C5 111.89(11) . .
N5 N1 C8 110.26(11) . .
N5 N1 Cu1 134.87(9) . .
C8 N1 Cu1 114.43(9) . .
C1 N2 C7 108.52(10) 2 .
C1 N2 C6 108.46(10) 2 .
C7 N2 C6 106.72(10) . .
C1 N2 Cu1 116.59(8) 2 .
C7 N2 Cu1 108.33(8) . .
C6 N2 Cu1 107.81(8) . .
N1 N5 N6 105.40(10) . .
N5 N6 C9 112.18(11) . .
N5 N6 C10 120.06(11) . .
C9 N6 C10 127.76(11) . .
N2 C1 C2 114.86(11) 2 .
N2 C1 H1A 108.8(10) 2 .
C2 C1 H1A 109.1(10) . .
N2 C1 H1B 108.2(10) 2 .
C2 C1 H1B 109.1(10) . .
H1A C1 H1B 106.5(14) . .
O3 C2 C1 112.07(11) . .
O3 C2 H2A 109.2 . .
C1 C2 H2A 109.2 . .
O3 C2 H2B 109.2 . .
C1 C2 H2B 109.2 . .
H2A C2 H2B 107.9 . .
O3 C3 C4 113.43(12) . .
O3 C3 H3A 108.9 . .
C4 C3 H3A 108.9 . .
O3 C3 H3B 108.9 . .
C4 C3 H3B 108.9 . .
H3A C3 H3B 107.7 . .
O1 C4 C3 111.07(12) . .
O1 C4 H4A 109.4 . .
C3 C4 H4A 109.4 . .
O1 C4 H4B 109.4 . .
C3 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
O1 C5 C6 107.02(11) . .
O1 C5 H5A 110.3 . .
C6 C5 H5A 110.3 . .
O1 C5 H5B 110.3 . .
C6 C5 H5B 110.3 . .
H5A C5 H5B 108.6 . .
C5 C6 N2 114.03(11) . .
C5 C6 H6A 108.7 . .
N2 C6 H6A 108.7 . .
C5 C6 H6B 108.7 . .
N2 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C8 C7 N2 108.14(10) . .
C8 C7 H7A 110.1 . .
N2 C7 H7A 110.1 . .
C8 C7 H7B 110.1 . .
N2 C7 H7B 110.1 . .
H7A C7 H7B 108.4 . .
N1 C8 C9 107.70(12) . .
N1 C8 C7 117.65(11) . .
C9 C8 C7 134.59(12) . .
N6 C9 C8 104.45(12) . .
N6 C9 H9 127.8 . .
C8 C9 H9 127.8 . .
C15 C10 C11 122.18(12) . .
C15 C10 N6 119.25(12) . .
C11 C10 N6 118.56(12) . .
C12 C11 C10 118.44(13) . .
C12 C11 H11 120.8 . .
C10 C11 H11 120.8 . .
C11 C12 C13 120.28(14) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C13 C14 120.46(13) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C10 C15 C14 118.73(13) . .
C10 C15 H15 120.6 . .
C14 C15 H15 120.6 . .
C15 C14 C13 119.88(14) . .
C15 C14 H14 120.1 . .
C13 C14 H14 120.1 . .
O23 Cl1 O22 109.88(8) . .
O23 Cl1 O21 109.94(8) . .
O22 Cl1 O21 109.41(7) . .
O23 Cl1 O24 109.11(7) . .
O22 Cl1 O24 109.18(7) . .
O21 Cl1 O24 109.30(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 2.0145(13) .
Cu1 N1 2.0145(13) 2
Cu1 N2 2.0958(13) .
Cu1 N2 2.0958(13) 2
O3 C3 1.4289(18) .
O3 C2 1.4316(17) .
O1 C4 1.4358(17) .
O1 C5 1.4360(16) .
N1 N5 1.3239(16) .
N1 C8 1.3558(17) .
N2 C1 1.4968(17) 2
N2 C7 1.4986(17) .
N2 C6 1.5088(17) .
N5 N6 1.3355(16) .
N6 C9 1.3521(17) .
N6 C10 1.4347(16) .
C1 N2 1.4968(17) 2
C1 C2 1.5111(19) .
C1 H1A 0.977(17) .
C1 H1B 0.950(17) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C4 1.507(2) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.5046(19) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.4827(18) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 C9 1.3657(18) .
C9 H9 0.9300 .
C10 C15 1.385(2) .
C10 C11 1.3918(19) .
C11 C12 1.3857(19) .
C11 H11 0.9300 .
C12 C13 1.390(2) .
C12 H12 0.9300 .
C13 C14 1.392(2) .
C13 H13 0.9300 .
C15 C14 1.390(2) .
C15 H15 0.9300 .
C14 H14 0.9300 .
Cl1 O23 1.4349(12) .
Cl1 O22 1.4393(12) .
Cl1 O21 1.4396(12) .
Cl1 O24 1.4493(12) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 Cu1 N1 N5 -28.81(12) 2 .
N2 Cu1 N1 N5 -162.68(13) . .
N2 Cu1 N1 N5 17.32(13) 2 .
N1 Cu1 N1 C8 142.70(14) 2 .
N2 Cu1 N1 C8 8.83(9) . .
N2 Cu1 N1 C8 -171.17(9) 2 .
N1 Cu1 N2 C1 -146.76(9) . 2
N1 Cu1 N2 C1 33.24(9) 2 2
N2 Cu1 N2 C1 109(45) 2 2
N1 Cu1 N2 C7 -24.08(8) . .
N1 Cu1 N2 C7 155.92(8) 2 .
N2 Cu1 N2 C7 -128(45) 2 .
N1 Cu1 N2 C6 91.06(9) . .
N1 Cu1 N2 C6 -88.94(9) 2 .
N2 Cu1 N2 C6 -13(45) 2 .
C8 N1 N5 N6 -0.57(14) . .
Cu1 N1 N5 N6 171.20(9) . .
N1 N5 N6 C9 0.22(14) . .
N1 N5 N6 C10 -179.30(11) . .
C3 O3 C2 C1 147.17(11) . .
N2 C1 C2 O3 -70.56(14) 2 .
C2 O3 C3 C4 -88.72(14) . .
C5 O1 C4 C3 161.24(11) . .
O3 C3 C4 O1 70.72(16) . .
C4 O1 C5 C6 -166.38(11) . .
O1 C5 C6 N2 -70.04(14) . .
C1 N2 C6 C5 -90.16(13) 2 .
C7 N2 C6 C5 153.11(11) . .
Cu1 N2 C6 C5 36.91(12) . .
C1 N2 C7 C8 161.46(10) 2 .
C6 N2 C7 C8 -81.84(12) . .
Cu1 N2 C7 C8 34.00(11) . .
N5 N1 C8 C9 0.71(14) . .
Cu1 N1 C8 C9 -172.89(8) . .
N5 N1 C8 C7 -176.99(11) . .
Cu1 N1 C8 C7 9.41(14) . .
N2 C7 C8 N1 -29.62(15) . .
N2 C7 C8 C9 153.46(14) . .
N5 N6 C9 C8 0.20(14) . .
C10 N6 C9 C8 179.68(12) . .
N1 C8 C9 N6 -0.54(14) . .
C7 C8 C9 N6 176.60(14) . .
N5 N6 C10 C15 -142.68(13) . .
C9 N6 C10 C15 37.88(19) . .
N5 N6 C10 C11 37.34(17) . .
C9 N6 C10 C11 -142.10(13) . .
C15 C10 C11 C12 0.6(2) . .
N6 C10 C11 C12 -179.44(12) . .
C10 C11 C12 C13 -1.4(2) . .
C11 C12 C13 C14 0.9(2) . .
C11 C10 C15 C14 0.9(2) . .
N6 C10 C15 C14 -179.11(12) . .
C10 C15 C14 C13 -1.5(2) . .
C12 C13 C14 C15 0.6(2) . .
