#------------------------------------------------------------------------------
#$Date: 2016-03-25 23:13:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180030 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/24/7032451.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_7032451
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         'C11 H8 Cu N6 O3'
_chemical_formula_sum            'C11 H8 Cu N6 O3'
_chemical_formula_weight         335.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5160(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.6607(3)
_cell_length_b                   7.4928(3)
_cell_length_c                   20.2477(7)
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.66
_cell_volume                     1161.10(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0184
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21901
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.66
_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_T_max  0.9277
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.765
_refine_diff_density_min         -0.604
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0411
_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)+(0.0585P)²+3.5266P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1096
_reflns_number_gt                2117
_reflns_number_total             2376
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7031837
_cod_data_source_file            c4dt01765j2.cif
_cod_data_source_block           b131023b_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7032451
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 1.18394(5) 1.06703(5) 0.441779(18) 0.01707(15) Uani 1 1 d U
O1 O 1.0829(3) 1.3399(3) 0.40509(11) 0.0251(5) Uani 1 1 d U
O2 O 0.9608(3) 1.3109(4) 0.30769(13) 0.0383(7) Uani 1 1 d U
O3 O 1.1956(4) 1.4653(5) 0.32086(15) 0.0452(8) Uani 1 1 d U
N1 N 0.9887(4) 0.9114(4) 0.42053(13) 0.0190(6) Uani 1 1 d U
N2 N 0.8597(3) 0.8846(4) 0.46264(13) 0.0170(5) Uani 1 1 d U
N3 N 0.5948(3) 0.8162(4) 0.52997(13) 0.0191(5) Uani 1 1 d U
N4 N 0.5092(3) 0.8795(4) 0.63280(14) 0.0210(6) Uani 1 1 d U
N5 N 0.6718(4) 0.9550(4) 0.64269(14) 0.0229(6) Uani 1 1 d U
N6 N 1.0801(3) 1.3723(4) 0.34340(14) 0.0218(6) Uani 1 1 d U
C1 C 0.9444(5) 0.8234(5) 0.36370(17) 0.0280(8) Uani 1 1 d U
H1 H 1.0121 0.8189 0.3267 0.034 Uiso 1 1 calc R
C2 C 0.7847(5) 0.7415(5) 0.36883(17) 0.0277(8) Uani 1 1 d U
H2 H 0.7241 0.6729 0.3371 0.033 Uiso 1 1 calc R
C3 C 0.7345(4) 0.7843(4) 0.43164(15) 0.0183(6) Uani 1 1 d U
C4 C 0.5783(4) 0.7508(4) 0.46839(16) 0.0195(6) Uani 1 1 d U
C5 C 0.4252(4) 0.6675(4) 0.44727(17) 0.0227(7) Uani 1 1 d U
H5 H 0.4119 0.6234 0.4044 0.027 Uiso 1 1 calc R
C6 C 0.2912(4) 0.6505(4) 0.49076(19) 0.0258(7) Uani 1 1 d U
H6 H 0.1880 0.5937 0.4770 0.031 Uiso 1 1 calc R
C7 C 0.3095(4) 0.7171(5) 0.55451(18) 0.0240(7) Uani 1 1 d U
H7 H 0.2212 0.7064 0.5844 0.029 Uiso 1 1 calc R
C8 C 0.4668(4) 0.8004(4) 0.57124(16) 0.0200(6) Uani 1 1 d U
C9 C 0.4132(5) 0.8991(5) 0.68705(18) 0.0274(7) Uani 1 1 d U
H9 H 0.2993 0.8598 0.6918 0.033 Uiso 1 1 calc R
C10 C 0.5140(5) 0.9865(5) 0.73302(18) 0.0302(8) Uani 1 1 d U
H10 H 0.4832 1.0192 0.7753 0.036 Uiso 1 1 calc R
C11 C 0.6740(5) 1.0178(5) 0.70423(17) 0.0281(8) Uani 1 1 d U
H11 H 0.7690 1.0747 0.7253 0.034 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'
O O 0.0106 0.0060 '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 N3 168.97(11) . 3_776
N1 Cu1 N2 99.40(11) . 3_776
N3 Cu1 N2 79.50(11) 3_776 3_776
N1 Cu1 N5 101.72(11) . 3_776
N3 Cu1 N5 78.05(11) 3_776 3_776
N2 Cu1 N5 157.04(11) 3_776 3_776
N1 Cu1 O1 102.63(10) . .
N3 Cu1 O1 88.40(10) 3_776 .
N2 Cu1 O1 94.76(10) 3_776 .
N5 Cu1 O1 89.34(10) 3_776 .
N6 O1 Cu1 118.6(2) . .
N2 N1 C1 107.5(3) . .
N2 N1 Cu1 122.1(2) . .
C1 N1 Cu1 130.2(2) . .
N1 N2 C3 108.3(3) . .
N1 N2 Cu1 137.6(2) . 3_776
C3 N2 Cu1 113.8(2) . 3_776
C8 N3 C4 120.9(3) . .
C8 N3 Cu1 120.6(2) . 3_776
C4 N3 Cu1 118.5(2) . 3_776
C9 N4 N5 110.9(3) . .
C9 N4 C8 130.7(3) . .
N5 N4 C8 118.4(3) . .
C11 N5 N4 104.8(3) . .
C11 N5 Cu1 144.2(2) . 3_776
N4 N5 Cu1 111.0(2) . 3_776
O2 N6 O3 121.5(3) . .
O2 N6 O1 119.1(3) . .
O3 N6 O1 119.4(3) . .
N1 C1 C2 110.0(3) . .
C1 C2 C3 104.5(3) . .
N2 C3 C2 109.6(3) . .
N2 C3 C4 116.1(3) . .
C2 C3 C4 134.2(3) . .
N3 C4 C5 119.8(3) . .
N3 C4 C3 111.4(3) . .
C5 C4 C3 128.7(3) . .
C4 C5 C6 119.2(3) . .
C7 C6 C5 120.7(3) . .
C6 C7 C8 116.2(3) . .
N3 C8 C7 123.2(3) . .
N3 C8 N4 112.0(3) . .
C7 C8 N4 124.8(3) . .
C10 C9 N4 107.3(3) . .
C9 C10 C11 106.2(3) . .
N5 C11 C10 110.8(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.930(3) .
Cu1 N3 1.970(3) 3_776
Cu1 N2 2.011(3) 3_776
Cu1 N5 2.083(3) 3_776
Cu1 O1 2.298(2) .
O1 N6 1.272(4) .
O2 N6 1.229(4) .
O3 N6 1.229(4) .
N1 N2 1.348(4) .
N1 C1 1.357(4) .
N2 C3 1.351(4) .
N2 Cu1 2.011(3) 3_776
N3 C8 1.322(4) .
N3 C4 1.341(4) .
N3 Cu1 1.970(3) 3_776
N4 C9 1.356(4) .
N4 N5 1.375(4) .
N4 C8 1.405(4) .
N5 C11 1.331(5) .
N5 Cu1 2.083(3) 3_776
C1 C2 1.377(5) .
C2 C3 1.382(5) .
C3 C4 1.458(5) .
C4 C5 1.380(4) .
C5 C6 1.387(5) .
C6 C7 1.385(5) .
C7 C8 1.386(5) .
C9 C10 1.352(6) .
C10 C11 1.400(5) .
