#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:13:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180030 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/24/7032452.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_7032452
loop_
_publ_author_name
'Tan, Da-Wei'
'Xie, Jing-Bo'
'Li, Qi'
'Li, Hong-Xi'
'Li, Jun-Chi'
'Li, Hai-Yan'
'Lang, Jian-Ping'
_publ_section_title
;
 Syntheses and structures of copper complexes of
 3-(6-(1H-pyrazol-1-yl)pyridin-2-yl)pyrazol-1-ide and their excellent
 performance in the syntheses of nitriles and aldehydes.
;
_journal_issue                   37
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14061
_journal_page_last               14071
_journal_paper_doi               10.1039/c4dt01765j
_journal_volume                  43
_journal_year                    2014
_chemical_formula_moiety         'C22 H16 Cl2 Cu2 N10 O8'
_chemical_formula_sum            'C22 H16 Cl2 Cu2 N10 O8'
_chemical_formula_weight         746.43
_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                97.366(4)
_cell_angle_beta                 91.381(5)
_cell_angle_gamma                102.354(6)
_cell_formula_units_Z            1
_cell_length_a                   7.9591(6)
_cell_length_b                   8.4441(5)
_cell_length_c                   9.9410(5)
_cell_measurement_reflns_used    1762
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      29.6420
_cell_measurement_theta_min      3.9260
_cell_volume                     646.34(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4866
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    1.924
_exptl_absorpt_correction_T_max  0.8613
_exptl_absorpt_correction_T_min  0.5133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             374
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         2.900
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.132
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0693
_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)+(0.1000P)²+1.8934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1807
_refine_ls_wR_factor_ref         0.1924
_reflns_number_gt                1983
_reflns_number_total             2412
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7031838
_cod_data_source_file            c4dt01765j2.cif
_cod_data_source_block           g140320a
_cod_database_code               7032452
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 0.17604(9) 0.47878(8) 0.37022(7) 0.0326(3) Uani 1 1 d . . .
Cl3 Cl 0.16307(19) 0.80130(18) 0.17891(15) 0.0367(4) Uani 1 1 d . . .
O1 O 0.0965(15) 0.6324(14) 0.1911(11) 0.0454(17) Uiso 0.50 1 d P A 1
O2 O 0.0780(15) 0.9183(13) 0.2507(13) 0.051(2) Uiso 0.50 1 d P A 1
O3 O 0.1546(17) 0.8229(14) 0.0393(12) 0.058(2) Uiso 0.50 1 d P A 1
O4 O 0.3410(17) 0.8581(15) 0.2370(11) 0.056(2) Uiso 0.50 1 d P A 1
O1A O 0.0808(15) 0.6522(14) 0.2293(11) 0.0454(17) Uiso 0.50 1 d P A 2
O2A O 0.127(3) 0.903(2) 0.312(2) 0.051(2) Uiso 0.25 1 d P A 2
O2B O 0.039(3) 0.897(3) 0.176(3) 0.051(2) Uiso 0.25 1 d P A 2
O3A O 0.067(3) 0.856(3) 0.084(2) 0.058(2) Uiso 0.25 1 d P A 2
O3B O 0.159(3) 0.755(3) 0.029(2) 0.058(2) Uiso 0.25 1 d P A 2
O4A O 0.3450(17) 0.8372(16) 0.1913(12) 0.056(2) Uiso 0.50 1 d P A 2
N1 N 0.0495(7) 0.6593(6) 0.6318(5) 0.0383(6) Uani 1 1 d . . .
N2 N 0.1677(7) 0.6312(6) 0.5420(5) 0.0383(6) Uani 1 1 d . A .
N3 N 0.4157(7) 0.6016(7) 0.3906(5) 0.0367(9) Uani 1 1 d . A .
N4 N 0.4568(8) 0.4358(7) 0.2033(6) 0.0502(8) Uani 1 1 d . . .
N5 N 0.2849(8) 0.3625(7) 0.2088(6) 0.0502(8) Uani 1 1 d . A .
C1 C 0.1283(8) 0.7930(8) 0.7215(6) 0.0383(6) Uani 1 1 d . A .
H1 H 0.0749 0.8412 0.7943 0.046 Uiso 1 1 calc R . .
C2 C 0.2938(8) 0.8459(8) 0.6906(6) 0.0383(6) Uani 1 1 d . . .
H2 H 0.3761 0.9341 0.7369 0.046 Uiso 1 1 calc R A .
C3 C 0.3156(8) 0.7422(8) 0.5765(6) 0.0383(6) Uani 1 1 d . A .
C4 C 0.4598(8) 0.7261(8) 0.4915(6) 0.0383(14) Uani 1 1 d . . .
C5 C 0.6243(9) 0.8182(9) 0.5068(7) 0.0479(17) Uani 1 1 d . A .
H5 H 0.6470 0.9012 0.5816 0.057 Uiso 1 1 calc R B 1
C6 C 0.746(2) 0.807(2) 0.4359(18) 0.043(5) Uiso 0.50 1 d P A 1
H6 H 0.8561 0.8762 0.4529 0.052 Uiso 0.50 1 calc PR A 1
C7 C 0.7042(18) 0.676(2) 0.3241(17) 0.031(4) Uiso 0.50 1 d P A 1
H7 H 0.7894 0.6593 0.2635 0.037 Uiso 0.50 1 calc PR A 1
C6A C 0.7418(18) 0.766(2) 0.4023(17) 0.031(4) Uiso 0.50 1 d P A 2
H6A H 0.8573 0.8234 0.4081 0.038 Uiso 0.50 1 calc PR A 2
C7A C 0.688(2) 0.633(2) 0.2943(16) 0.039(4) Uiso 0.50 1 d P A 2
H7A H 0.7596 0.5992 0.2276 0.047 Uiso 0.50 1 calc PR A 2
C8 C 0.5291(8) 0.5680(8) 0.3021(6) 0.0367(9) Uani 1 1 d . A .
C9 C 0.5280(10) 0.3592(9) 0.0974(7) 0.0502(8) Uani 1 1 d . A 1
H9 H 0.6435 0.3853 0.0741 0.060 Uiso 1 1 calc R A 1
C10 C 0.4046(10) 0.2413(9) 0.0336(7) 0.0502(8) Uani 1 1 d . A 1
H10 H 0.4162 0.1694 -0.0442 0.060 Uiso 1 1 calc R A 1
C11 C 0.2534(10) 0.2427(9) 0.1025(7) 0.0502(8) Uani 1 1 d . A 1
H11 H 0.1464 0.1709 0.0782 0.060 Uiso 1 1 calc R A 1
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'
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'
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'
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 172.1(2) 2_566 .
N1 Cu1 N2 99.0(2) 2_566 .
N3 Cu1 N2 79.7(2) . .
N1 Cu1 N5 102.3(2) 2_566 .
N3 Cu1 N5 78.3(2) . .
N2 Cu1 N5 157.8(3) . .
N1 Cu1 O1A 92.7(3) 2_566 .
N3 Cu1 O1A 95.2(3) . .
N2 Cu1 O1A 93.4(3) . .
N5 Cu1 O1A 91.8(3) . .
O3A Cl3 O2B 41.1(11) . .
O3A Cl3 O4A 124.7(11) . .
O2B Cl3 O4A 134.0(10) . .
O3A Cl3 O3 38.0(10) . .
O2B Cl3 O3 78.0(11) . .
O4A Cl3 O3 94.7(7) . .
O3A Cl3 O1 111.9(10) . .
O2B Cl3 O1 115.3(10) . .
O4A Cl3 O1 110.0(7) . .
O3 Cl3 O1 109.0(6) . .
O3A Cl3 O2 72.1(10) . .
O2B Cl3 O2 31.8(9) . .
O4A Cl3 O2 116.9(7) . .
O3 Cl3 O2 106.6(7) . .
O1 Cl3 O2 116.9(6) . .
O3A Cl3 O1A 116.2(11) . .
O2B Cl3 O1A 106.8(10) . .
O4A Cl3 O1A 114.6(7) . .
O3 Cl3 O1A 123.3(6) . .
O1 Cl3 O1A 17.1(6) . .
O2 Cl3 O1A 101.5(6) . .
O3A Cl3 O4 133.4(11) . .
O2B Cl3 O4 125.8(11) . .
O4A Cl3 O4 18.6(7) . .
O3 Cl3 O4 110.6(7) . .
O1 Cl3 O4 111.6(7) . .
O2 Cl3 O4 101.8(7) . .
O1A Cl3 O4 110.3(7) . .
O3A Cl3 O3B 54.6(14) . .
O2B Cl3 O3B 95.6(14) . .
O4A Cl3 O3B 93.0(11) . .
O3 Cl3 O3B 22.9(9) . .
O1 Cl3 O3B 88.4(10) . .
O2 Cl3 O3B 126.6(11) . .
O1A Cl3 O3B 104.2(10) . .
O4 Cl3 O3B 111.5(11) . .
O3A Cl3 O2A 101.1(13) . .
O2B Cl3 O2A 60.6(11) . .
O4A Cl3 O2A 99.2(10) . .
O3 Cl3 O2A 133.6(9) . .
O1 Cl3 O2A 107.2(9) . .
O2 Cl3 O2A 29.0(7) . .
O1A Cl3 O2A 90.1(9) . .
O4 Cl3 O2A 81.1(9) . .
O3B Cl3 O2A 155.3(12) . .
Cl3 O1A Cu1 134.0(7) . .
N2 N1 C1 106.4(5) . .
N2 N1 Cu1 123.4(4) . 2_566
C1 N1 Cu1 130.2(4) . 2_566
C3 N2 N1 108.8(5) . .
C3 N2 Cu1 113.8(4) . .
N1 N2 Cu1 137.3(4) . .
C8 N3 C4 120.7(6) . .
C8 N3 Cu1 120.7(5) . .
C4 N3 Cu1 118.5(4) . .
C9 N4 N5 110.6(6) . .
C9 N4 C8 131.1(6) . .
N5 N4 C8 118.4(5) . .
C11 N5 N4 104.7(5) . .
C11 N5 Cu1 144.6(6) . .
N4 N5 Cu1 110.7(4) . .
C2 C1 N1 110.5(6) . .
C2 C1 H1 124.8 . .
N1 C1 H1 124.8 . .
C1 C2 C3 105.0(6) . .
C1 C2 H2 127.5 . .
C3 C2 H2 127.5 . .
N2 C3 C2 109.3(6) . .
N2 C3 C4 116.0(5) . .
C2 C3 C4 134.7(6) . .
N3 C4 C5 120.3(6) . .
N3 C4 C3 111.7(5) . .
C5 C4 C3 127.9(6) . .
C6 C5 C4 128.7(11) . .
C6 C5 C6A 14.8(10) . .
C4 C5 C6A 114.0(9) . .
C6 C5 H5 115.7 . .
C4 C5 H5 115.7 . .
C6A C5 H5 130.3 . .
C5 C6 C7 113.1(14) . .
C5 C6 H6 123.5 . .
C7 C6 H6 123.5 . .
C6 C7 C8 121.7(12) . .
C6 C7 H7 119.2 . .
C8 C7 H7 119.2 . .
C7A C6A C5 123.8(12) . .
C7A C6A H6A 118.1 . .
C5 C6A H6A 118.1 . .
C8 C7A C6A 109.9(13) . .
C8 C7A H7A 125.1 . .
C6A C7A H7A 125.1 . .
C7A C8 N3 131.2(10) . .
C7A C8 N4 116.9(10) . .
N3 C8 N4 111.9(6) . .
C7A C8 C7 15.8(9) . .
N3 C8 C7 115.5(8) . .
N4 C8 C7 132.6(8) . .
C10 C9 N4 107.3(7) . .
C10 C9 H9 126.4 . .
N4 C9 H9 126.4 . .
C9 C10 C11 107.9(7) . .
C9 C10 H10 126.0 . .
C11 C10 H10 126.0 . .
N5 C11 C10 109.6(7) . .
N5 C11 H11 125.2 . .
C10 C11 H11 125.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.918(5) 2_566
Cu1 N3 1.959(5) .
Cu1 N2 2.014(5) .
Cu1 N5 2.078(5) .
Cu1 O1A 2.373(12) .
Cl3 O3A 1.38(2) .
Cl3 O2B 1.41(2) .
Cl3 O4A 1.414(13) .
Cl3 O3 1.424(12) .
Cl3 O1 1.433(12) .
Cl3 O2 1.439(10) .
Cl3 O1A 1.445(12) .
Cl3 O4 1.473(13) .
Cl3 O3B 1.49(2) .
Cl3 O2A 1.55(2) .
N1 N2 1.349(7) .
N1 C1 1.369(8) .
N1 Cu1 1.918(5) 2_566
N2 C3 1.345(8) .
N3 C8 1.324(8) .
N3 C4 1.338(8) .
N4 C9 1.363(8) .
N4 N5 1.382(9) .
N4 C8 1.400(9) .
N5 C11 1.344(9) .
C1 C2 1.354(9) .
C1 H1 0.9400 .
C2 C3 1.380(8) .
C2 H2 0.9400 .
C3 C4 1.460(9) .
C4 C5 1.366(9) .
C5 C6 1.227(18) .
C5 C6A 1.502(17) .
C5 H5 0.9400 .
C6 C7 1.44(2) .
C6 H6 0.9400 .
C7 C8 1.489(16) .
C7 H7 0.9400 .
C6A C7A 1.43(2) .
C6A H6A 0.9400 .
C7A C8 1.277(17) .
C7A H7A 0.9400 .
C9 C10 1.322(11) .
C9 H9 0.9400 .
C10 C11 1.400(9) .
C10 H10 0.9400 .
C11 H11 0.9400 .
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
O3A Cl3 O1A Cu1 172.6(13) .
O2B Cl3 O1A Cu1 -144.1(13) .
O4A Cl3 O1A Cu1 15.3(11) .
O3 Cl3 O1A Cu1 129.4(9) .
O1 Cl3 O1A Cu1 93(3) .
O2 Cl3 O1A Cu1 -111.7(9) .
O4 Cl3 O1A Cu1 -4.4(10) .
O3B Cl3 O1A Cu1 115.4(12) .
O2A Cl3 O1A Cu1 -84.9(11) .
N1 Cu1 O1A Cl3 176.5(8) 2_566
N3 Cu1 O1A Cl3 -2.7(8) .
N2 Cu1 O1A Cl3 77.3(8) .
N5 Cu1 O1A Cl3 -81.1(8) .
C1 N1 N2 C3 1.0(7) .
Cu1 N1 N2 C3 -175.5(4) 2_566
C1 N1 N2 Cu1 -175.1(5) .
Cu1 N1 N2 Cu1 8.3(9) 2_566
N1 Cu1 N2 C3 176.9(4) 2_566
N3 Cu1 N2 C3 4.9(4) .
N5 Cu1 N2 C3 13.4(9) .
O1A Cu1 N2 C3 -89.8(5) .
N1 Cu1 N2 N1 -7.0(7) 2_566
N3 Cu1 N2 N1 -179.1(7) .
N5 Cu1 N2 N1 -170.5(6) .
O1A Cu1 N2 N1 86.2(7) .
N1 Cu1 N3 C8 97.8(15) 2_566
N2 Cu1 N3 C8 179.1(5) .
N5 Cu1 N3 C8 2.4(4) .
O1A Cu1 N3 C8 -88.3(5) .
N1 Cu1 N3 C4 -85.9(15) 2_566
N2 Cu1 N3 C4 -4.6(4) .
N5 Cu1 N3 C4 178.7(5) .
O1A Cu1 N3 C4 88.0(5) .
C9 N4 N5 C11 -1.3(7) .
C8 N4 N5 C11 179.6(6) .
C9 N4 N5 Cu1 179.9(4) .
C8 N4 N5 Cu1 0.9(7) .
N1 Cu1 N5 C11 8.5(9) 2_566
N3 Cu1 N5 C11 -179.6(9) .
N2 Cu1 N5 C11 171.8(7) .
O1A Cu1 N5 C11 -84.6(9) .
N1 Cu1 N5 N4 -173.5(4) 2_566
N3 Cu1 N5 N4 -1.6(4) .
N2 Cu1 N5 N4 -10.2(8) .
O1A Cu1 N5 N4 93.4(5) .
N2 N1 C1 C2 -1.3(7) .
Cu1 N1 C1 C2 174.9(4) 2_566
N1 C1 C2 C3 1.0(7) .
N1 N2 C3 C2 -0.4(7) .
Cu1 N2 C3 C2 176.7(4) .
N1 N2 C3 C4 178.2(5) .
Cu1 N2 C3 C4 -4.7(7) .
C1 C2 C3 N2 -0.4(7) .
C1 C2 C3 C4 -178.6(7) .
C8 N3 C4 C5 -1.7(9) .
Cu1 N3 C4 C5 -178.0(4) .
C8 N3 C4 C3 179.6(5) .
Cu1 N3 C4 C3 3.3(7) .
N2 C3 C4 N3 1.1(8) .
C2 C3 C4 N3 179.2(7) .
N2 C3 C4 C5 -177.5(6) .
C2 C3 C4 C5 0.6(12) .
N3 C4 C5 C6 2.0(14) .
C3 C4 C5 C6 -179.5(11) .
N3 C4 C5 C6A 0.3(10) .
C3 C4 C5 C6A 178.7(8) .
C4 C5 C6 C7 -0.7(19) .
C6A C5 C6 C7 6(3) .
C5 C6 C7 C8 -0.8(19) .
C6 C5 C6A C7A -174(5) .
C4 C5 C6A C7A 0.9(15) .
C5 C6A C7A C8 -0.5(18) .
C6A C7A C8 N3 -1.1(18) .
C6A C7A C8 N4 -179.9(9) .
C6A C7A C8 C7 6(3) .
C4 N3 C8 C7A 2.3(13) .
Cu1 N3 C8 C7A 178.6(10) .
C4 N3 C8 N4 -178.8(5) .
Cu1 N3 C8 N4 -2.6(7) .
C4 N3 C8 C7 0.3(9) .
Cu1 N3 C8 C7 176.5(6) .
C9 N4 C8 C7A 1.1(13) .
N5 N4 C8 C7A 180.0(9) .
C9 N4 C8 N3 -177.9(6) .
N5 N4 C8 N3 1.0(8) .
C9 N4 C8 C7 3.2(13) .
N5 N4 C8 C7 -177.9(9) .
C6 C7 C8 C7A -173(5) .
C6 C7 C8 N3 1.0(15) .
C6 C7 C8 N4 179.9(10) .
N5 N4 C9 C10 1.4(8) .
C8 N4 C9 C10 -179.7(7) .
N4 C9 C10 C11 -0.9(8) .
N4 N5 C11 C10 0.7(8) .
Cu1 N5 C11 C10 178.7(6) .
C9 C10 C11 N5 0.2(9) .
