#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/40/7054000.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_7054000
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         'C32 H44 Cu N8 O4, 2(Cl O4)'
_chemical_formula_sum            'C32 H44 Cl2 Cu N8 O12'
_chemical_formula_weight         867.19
_chemical_name_common            '[CuL1](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                98.876(4)
_cell_angle_beta                 108.784(5)
_cell_angle_gamma                105.480(6)
_cell_formula_units_Z            1
_cell_length_a                   9.1849(15)
_cell_length_b                   9.2931(8)
_cell_length_c                   11.8913(12)
_cell_measurement_reflns_used    8835
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.49
_cell_volume                     893.4(2)
_computing_cell_refinement       HKL2000
_computing_data_collection       'Collect Bruker-Nonius'
_computing_data_reduction        HKL2000
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR92
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius KappaApex'
_diffrn_measurement_method       'ω 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  0.0145
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8835
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.920
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(see. N.W. Alcock (1970). Cryst. Computing, p271)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             451
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0322P)²+0.6072P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0696
_reflns_number_gt                4153
_reflns_number_total             4418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3nj00570d.txt
_cod_data_source_block           shelxl
_cod_original_cell_volume        893.40(19)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7054000
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 0.5000 0.5000 0.5000 0.01153(6) Uani 1 2 d S
O3 O 0.73134(12) 0.28922(12) 0.34770(10) 0.0190(2) Uani 1 1 d .
O1 O 0.43089(12) 0.74096(11) 0.47239(9) 0.01679(19) Uani 1 1 d .
N1 N 0.70919(13) 0.60968(13) 0.64366(10) 0.0134(2) Uani 1 1 d .
N2 N 0.65100(13) 0.58497(13) 0.40634(10) 0.0126(2) Uani 1 1 d .
N3 N 0.75044(13) 0.64538(13) 0.76477(10) 0.0142(2) Uani 1 1 d .
N4 N 0.91240(13) 0.70847(13) 0.81270(10) 0.0130(2) Uani 1 1 d .
C1 C 0.61446(16) 0.48356(15) 0.28263(12) 0.0148(2) Uani 1 1 d .
H1A H 0.7072 0.5223 0.2574 0.018 Uiso 1 1 calc R
H1B H 0.5167 0.4931 0.2220 0.018 Uiso 1 1 calc R
C2 C 0.58462(17) 0.31384(16) 0.27749(12) 0.0165(3) Uani 1 1 d .
H2A H 0.4994 0.2763 0.3103 0.020 Uiso 1 1 calc R
H2B H 0.5442 0.2535 0.1907 0.020 Uiso 1 1 calc R
C3 C 0.70526(18) 0.16554(17) 0.40460(14) 0.0199(3) Uani 1 1 d .
H3A H 0.7900 0.1172 0.4082 0.024 Uiso 1 1 calc R
H3B H 0.5976 0.0859 0.3529 0.024 Uiso 1 1 calc R
C4 C 0.28982(18) 0.78375(18) 0.46685(14) 0.0203(3) Uani 1 1 d .
H4A H 0.1891 0.6944 0.4173 0.024 Uiso 1 1 calc R
H4B H 0.2882 0.8692 0.4266 0.024 Uiso 1 1 calc R
C5 C 0.46432(17) 0.74368(16) 0.36287(12) 0.0166(3) Uani 1 1 d .
H5A H 0.4564 0.8390 0.3379 0.020 Uiso 1 1 calc R
H5B H 0.3849 0.6530 0.2946 0.020 Uiso 1 1 calc R
C6 C 0.63536(16) 0.73928(15) 0.39259(12) 0.0160(2) Uani 1 1 d .
H6A H 0.6719 0.7660 0.3264 0.019 Uiso 1 1 calc R
H6B H 0.7093 0.8193 0.4701 0.019 Uiso 1 1 calc R
C7 C 0.82617(15) 0.61662(16) 0.48553(12) 0.0154(2) Uani 1 1 d .
H7A H 0.8582 0.5253 0.4652 0.018 Uiso 1 1 calc R
H7B H 0.8977 0.7059 0.4707 0.018 Uiso 1 1 calc R
C8 C 0.84471(15) 0.65093(15) 0.61660(12) 0.0132(2) Uani 1 1 d .
C9 C 0.97685(16) 0.71478(15) 0.72562(12) 0.0142(2) Uani 1 1 d .
H9 H 1.0888 0.7546 0.7374 0.017 Uiso 1 1 calc R
C10 C 0.99903(16) 0.77312(16) 0.94702(12) 0.0154(2) Uani 1 1 d .
H10A H 0.9332 0.7199 0.9896 0.018 Uiso 1 1 calc R
H10B H 1.0130 0.8845 0.9690 0.018 Uiso 1 1 calc R
C11 C 1.16421(16) 0.75318(15) 0.98904(11) 0.0138(2) Uani 1 1 d .
C12 C 1.17698(17) 0.60609(16) 0.96791(12) 0.0171(3) Uani 1 1 d .
H12 H 1.0810 0.5176 0.9274 0.021 Uiso 1 1 calc R
C13 C 1.32955(18) 0.58834(17) 1.00592(13) 0.0189(3) Uani 1 1 d .
H13 H 1.3377 0.4878 0.9923 0.023 Uiso 1 1 calc R
C14 C 1.47021(17) 0.71786(17) 1.06396(12) 0.0183(3) Uani 1 1 d .
H14 H 1.5746 0.7060 1.0892 0.022 Uiso 1 1 calc R
C15 C 1.45801(17) 0.86461(17) 1.08493(12) 0.0181(3) Uani 1 1 d .
H15 H 1.5541 0.9530 1.1249 0.022 Uiso 1 1 calc R
C16 C 1.30543(16) 0.88250(16) 1.04749(12) 0.0164(2) Uani 1 1 d .
H16 H 1.2976 0.9831 1.0618 0.020 Uiso 1 1 calc R
Cl1 Cl 0.01921(4) 0.09988(4) 0.75179(3) 0.01646(8) Uani 1 1 d .
O32 O 0.05806(16) 0.26561(13) 0.78098(11) 0.0318(3) Uani 1 1 d .
O31 O 0.14905(14) 0.06346(14) 0.83508(12) 0.0336(3) Uani 1 1 d .
O33 O -0.13104(14) 0.02694(14) 0.76534(11) 0.0271(2) Uani 1 1 d .
O34 O 0.00221(15) 0.04457(14) 0.62685(10) 0.0300(3) 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 180.0 2_666 .
N1 Cu1 N2 99.28(4) 2_666 .
N1 Cu1 N2 80.72(4) . .
N1 Cu1 N2 80.72(4) 2_666 2_666
N1 Cu1 N2 99.28(4) . 2_666
N2 Cu1 N2 180.0 . 2_666
C3 O3 C2 114.41(11) . .
C5 O1 C4 112.30(10) . .
N3 N1 C8 110.15(10) . .
N3 N1 Cu1 134.21(9) . .
C8 N1 Cu1 115.50(9) . .
C7 N2 C1 108.24(10) . .
C7 N2 C6 106.47(10) . .
C1 N2 C6 109.49(10) . .
C7 N2 Cu1 109.52(8) . .
C1 N2 Cu1 116.24(8) . .
C6 N2 Cu1 106.46(8) . .
N1 N3 N4 105.42(10) . .
N3 N4 C9 112.45(11) . .
N3 N4 C10 119.81(11) . .
C9 N4 C10 127.54(11) . .
N2 C1 C2 114.84(10) . .
N2 C1 H1A 108.6 . .
C2 C1 H1A 108.6 . .
N2 C1 H1B 108.6 . .
C2 C1 H1B 108.6 . .
H1A C1 H1B 107.5 . .
O3 C2 C1 111.35(11) . .
O3 C2 H2A 109.4 . .
C1 C2 H2A 109.4 . .
O3 C2 H2B 109.4 . .
C1 C2 H2B 109.4 . .
H2A C2 H2B 108.0 . .
O3 C3 C4 113.40(12) . 2_666
O3 C3 H3A 108.9 . .
C4 C3 H3A 108.9 2_666 .
O3 C3 H3B 108.9 . .
C4 C3 H3B 108.9 2_666 .
H3A C3 H3B 107.7 . .
O1 C4 C3 109.80(11) . 2_666
O1 C4 H4A 109.7 . .
C3 C4 H4A 109.7 2_666 .
O1 C4 H4B 109.7 . .
C3 C4 H4B 109.7 2_666 .
H4A C4 H4B 108.2 . .
O1 C5 C6 106.89(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 . .
N2 C6 C5 114.01(11) . .
N2 C6 H6A 108.7 . .
C5 C6 H6A 108.7 . .
N2 C6 H6B 108.7 . .
C5 C6 H6B 108.7 . .
H6A C6 H6B 107.6 . .
C8 C7 N2 108.56(10) . .
C8 C7 H7A 110.0 . .
N2 C7 H7A 110.0 . .
C8 C7 H7B 110.0 . .
N2 C7 H7B 110.0 . .
H7A C7 H7B 108.4 . .
N1 C8 C9 107.51(11) . .
N1 C8 C7 118.90(11) . .
C9 C8 C7 133.54(12) . .
N4 C9 C8 104.47(11) . .
N4 C9 H9 127.8 . .
C8 C9 H9 127.8 . .
N4 C10 C11 110.55(10) . .
N4 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
N4 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
C16 C11 C12 119.56(12) . .
C16 C11 C10 119.95(12) . .
C12 C11 C10 120.48(12) . .
C13 C12 C11 120.29(13) . .
C13 C12 H12 119.9 . .
C11 C12 H12 119.9 . .
C14 C13 C12 119.93(13) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C15 C14 C13 119.95(13) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 120.19(13) . .
C14 C15 H15 119.9 . .
C16 C15 H15 119.9 . .
C15 C16 C11 120.08(13) . .
C15 C16 H16 120.0 . .
C11 C16 H16 120.0 . .
O33 Cl1 O34 109.43(7) . .
O33 Cl1 O31 109.03(8) . .
O34 Cl1 O31 110.13(8) . .
O33 Cl1 O32 110.15(8) . .
O34 Cl1 O32 109.17(7) . .
O31 Cl1 O32 108.93(7) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.9881(11) 2_666
Cu1 N1 1.9881(11) .
Cu1 N2 2.1140(11) .
Cu1 N2 2.1140(11) 2_666
O3 C3 1.4260(17) .
O3 C2 1.4369(16) .
O1 C5 1.4334(16) .
O1 C4 1.4386(16) .
N1 N3 1.3272(15) .
N1 C8 1.3570(16) .
N2 C7 1.4993(16) .
N2 C1 1.5001(16) .
N2 C6 1.5070(17) .
N3 N4 1.3292(15) .
N4 C9 1.3494(17) .
N4 C10 1.4750(16) .
C1 C2 1.5150(18) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.511(2) 2_666
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C3 1.511(2) 2_666
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.5085(19) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.4854(18) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.3678(18) .
C9 H9 0.9500 .
C10 C11 1.5087(18) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C16 1.3927(19) .
C11 C12 1.3942(18) .
C12 C13 1.391(2) .
C12 H12 0.9500 .
C13 C14 1.391(2) .
C13 H13 0.9500 .
C14 C15 1.389(2) .
C14 H14 0.9500 .
C15 C16 1.3911(19) .
C15 H15 0.9500 .
C16 H16 0.9500 .
Cl1 O33 1.4379(11) .
Cl1 O34 1.4380(11) .
Cl1 O31 1.4409(12) .
Cl1 O32 1.4428(11) .
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 N3 17(100) 2_666 .
N2 Cu1 N1 N3 170.97(13) . .
N2 Cu1 N1 N3 -9.03(13) 2_666 .
N1 Cu1 N1 C8 -168(100) 2_666 .
N2 Cu1 N1 C8 -14.01(9) . .
N2 Cu1 N1 C8 165.99(9) 2_666 .
N1 Cu1 N2 C7 -157.27(8) 2_666 .
N1 Cu1 N2 C7 22.73(8) . .
N2 Cu1 N2 C7 77(100) 2_666 .
N1 Cu1 N2 C1 -34.25(9) 2_666 .
N1 Cu1 N2 C1 145.75(9) . .
N2 Cu1 N2 C1 -160(100) 2_666 .
N1 Cu1 N2 C6 88.00(8) 2_666 .
N1 Cu1 N2 C6 -92.00(8) . .
N2 Cu1 N2 C6 -38(100) 2_666 .
C8 N1 N3 N4 -0.24(14) . .
Cu1 N1 N3 N4 174.98(9) . .
N1 N3 N4 C9 0.15(14) . .
N1 N3 N4 C10 175.30(11) . .
C7 N2 C1 C2 78.76(13) . .
C6 N2 C1 C2 -165.57(11) . .
Cu1 N2 C1 C2 -44.93(13) . .
C3 O3 C2 C1 146.96(11) . .
N2 C1 C2 O3 -68.15(14) . .
C2 O3 C3 C4 -90.76(14) . 2_666
C5 O1 C4 C3 -159.78(11) . 2_666
C4 O1 C5 C6 165.26(11) . .
C7 N2 C6 C5 -156.14(11) . .
C1 N2 C6 C5 87.06(13) . .
Cu1 N2 C6 C5 -39.35(12) . .
O1 C5 C6 N2 71.83(14) . .
C1 N2 C7 C8 -154.38(10) . .
C6 N2 C7 C8 87.99(12) . .
Cu1 N2 C7 C8 -26.73(12) . .
N3 N1 C8 C9 0.25(15) . .
Cu1 N1 C8 C9 -175.96(9) . .
N3 N1 C8 C7 178.14(11) . .
Cu1 N1 C8 C7 1.94(15) . .
N2 C7 C8 N1 17.40(16) . .
N2 C7 C8 C9 -165.37(14) . .
N3 N4 C9 C8 0.00(15) . .
C10 N4 C9 C8 -174.70(12) . .
N1 C8 C9 N4 -0.14(14) . .
C7 C8 C9 N4 -177.60(14) . .
N3 N4 C10 C11 147.40(12) . .
C9 N4 C10 C11 -38.25(18) . .
N4 C10 C11 C16 120.08(13) . .
N4 C10 C11 C12 -58.79(16) . .
C16 C11 C12 C13 0.6(2) . .
C10 C11 C12 C13 179.49(12) . .
C11 C12 C13 C14 -0.8(2) . .
C12 C13 C14 C15 0.6(2) . .
C13 C14 C15 C16 -0.3(2) . .
C14 C15 C16 C11 0.1(2) . .
C12 C11 C16 C15 -0.3(2) . .
C10 C11 C16 C15 -179.18(12) . .
