#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220860.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220860
loop_
_publ_author_name
'Hu, Fei-long'
'Yin, Xian-hong'
'Feng, Yu'
'Mi, Yan'
'Zhang, Shan-shan'
_publ_section_title
;
 Diaqua(5-methyl-1H-pyrazole-3-carboxylato)(4-nitrobenzoato)copper(II)
;
_journal_coeditor_code           LH2751
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m210
_journal_paper_doi               10.1107/S160053680900169X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C7 H4 N O4) (C5 H5 N2 O2) (H2 O)2]'
_chemical_formula_moiety         'C12 H13 Cu N3 O8'
_chemical_formula_sum            'C12 H13 Cu N3 O8'
_chemical_formula_weight         390.79
_chemical_name_systematic
;
Diaqua(5-methyl-1H-pyrazole-3-carboxylato)(4-nitrobenzoato)copper(II)
;
_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                96.6330(10)
_cell_angle_beta                 105.116(2)
_cell_angle_gamma                103.978(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9650(10)
_cell_length_b                   9.1860(13)
_cell_length_c                   12.4220(16)
_cell_measurement_reflns_used    2564
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.623
_cell_volume                     730.91(18)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1996)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0126
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3783
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  0.7476
_exptl_absorpt_correction_T_min  0.5770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             398
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.324
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0276
_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)+(0.0335P)²+0.6897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0683
_refine_ls_wR_factor_ref         0.0726
_reflns_number_gt                2249
_reflns_number_total             2526
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2751.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        730.91(17)
_cod_database_code               2220860
_cod_database_fobs_code          2220860
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.29638(4) 0.19451(3) 0.99760(3) 0.02357(11) Uani d . 1 . .
O O1 0.5665(3) 0.2069(2) 0.96944(15) 0.0277(4) Uani d . 1 . .
O O2 0.7980(3) 0.3422(2) 0.89863(17) 0.0381(5) Uani d . 1 . .
O O3 0.1131(3) -0.0129(2) 0.85168(15) 0.0304(4) Uani d . 1 . .
O O4 -0.1882(3) -0.0059(3) 0.73675(17) 0.0436(5) Uani d . 1 . .
O O5 0.3529(4) 0.3559(3) 0.4025(2) 0.0652(7) Uani d . 1 . .
O O6 0.6072(4) 0.2702(4) 0.4743(3) 0.0742(9) Uani d . 1 . .
O O7 0.0648(3) 0.2226(2) 1.04985(15) 0.0300(4) Uani d . 1 . .
H H7A -0.0183 0.2515 0.9997 0.045 Uiso d R 1 . .
H H7B 0.0013 0.1397 1.0639 0.045 Uiso d R 1 . .
O O8 0.3635(3) 0.0686(2) 1.10838(15) 0.0307(4) Uani d . 1 . .
H H8A 0.3628 -0.0188 1.0768 0.046 Uiso d R 1 . .
H H8B 0.2798 0.0576 1.1478 0.046 Uiso d R 1 . .
N N1 0.2972(3) 0.3507(2) 0.90140(17) 0.0220(4) Uani d . 1 . .
N N2 0.1750(3) 0.4334(2) 0.85329(17) 0.0240(4) Uani d . 1 . .
H H2 0.0547 0.4290 0.8609 0.029 Uiso d R 1 . .
N N3 0.4354(4) 0.2843(3) 0.4672(2) 0.0445(6) Uani d . 1 . .
C C1 0.6256(4) 0.3104(3) 0.9141(2) 0.0240(5) Uani d . 1 . .
C C2 0.4692(3) 0.3913(3) 0.8697(2) 0.0212(5) Uani d . 1 . .
C C3 0.4564(4) 0.5001(3) 0.8016(2) 0.0265(5) Uani d . 1 . .
H H3 0.5558 0.5468 0.7693 0.032 Uiso calc R 1 . .
C C4 0.2652(4) 0.5246(3) 0.7917(2) 0.0265(5) Uani d . 1 . .
C C5 0.1576(5) 0.6251(4) 0.7292(3) 0.0449(8) Uani d . 1 . .
H H5A 0.0132 0.5718 0.6957 0.067 Uiso calc R 1 . .
H H5B 0.2181 0.6526 0.6707 0.067 Uiso calc R 1 . .
H H5C 0.1721 0.7159 0.7811 0.067 Uiso calc R 1 . .
C C6 0.0028(4) 0.0150(3) 0.7621(2) 0.0272(6) Uani d . 1 . .
C C7 0.1138(4) 0.0802(3) 0.6810(2) 0.0252(5) Uani d . 1 . .
C C8 0.3027(4) 0.0557(3) 0.6794(2) 0.0293(6) Uani d . 1 . .
H H8 0.3590 -0.0045 0.7267 0.035 Uiso calc R 1 . .
C C9 0.4072(4) 0.1196(3) 0.6083(2) 0.0321(6) Uani d . 1 . .
H H9 0.5324 0.1022 0.6064 0.038 Uiso calc R 1 . .
C C10 0.3217(4) 0.2099(3) 0.5403(2) 0.0311(6) Uani d . 1 . .
C C11 0.1344(4) 0.2360(3) 0.5388(2) 0.0344(6) Uani d . 1 . .
H H11 0.0796 0.2969 0.4916 0.041 Uiso calc R 1 . .
C C12 0.0298(4) 0.1692(3) 0.6095(2) 0.0318(6) Uani d . 1 . .
H H12 -0.0978 0.1841 0.6090 0.038 Uiso calc R 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O8 Cu1 O7 . . 91.42(7) ?
O8 Cu1 N1 . . 166.43(8) ?
O7 Cu1 N1 . . 96.45(7) ?
O8 Cu1 O1 . . 88.78(7) ?
O7 Cu1 O1 . . 167.50(8) ?
N1 Cu1 O1 . . 81.15(7) ?
O8 Cu1 O3 . . 93.71(7) ?
O7 Cu1 O3 . . 97.90(7) ?
N1 Cu1 O3 . . 96.12(7) ?
O1 Cu1 O3 . . 94.56(7) ?
C1 O1 Cu1 . . 115.62(15) ?
C6 O3 Cu1 . . 116.46(16) ?
Cu1 O7 H7A . . 110.3 ?
Cu1 O7 H7B . . 109.9 ?
H7A O7 H7B . . 109.5 ?
Cu1 O8 H8A . . 111.4 ?
Cu1 O8 H8B . . 111.3 ?
H8A O8 H8B . . 109.4 ?
C2 N1 N2 . . 105.59(19) ?
C2 N1 Cu1 . . 114.33(15) ?
N2 N1 Cu1 . . 140.08(16) ?
N1 N2 C4 . . 111.61(19) ?
N1 N2 H2 . . 124.2 ?
C4 N2 H2 . . 124.2 ?
O5 N3 O6 . . 123.2(3) ?
O5 N3 C10 . . 118.5(2) ?
O6 N3 C10 . . 118.3(2) ?
O2 C1 O1 . . 123.6(2) ?
O2 C1 C2 . . 121.8(2) ?
O1 C1 C2 . . 114.6(2) ?
N1 C2 C3 . . 110.7(2) ?
N1 C2 C1 . . 114.0(2) ?
C3 C2 C1 . . 135.4(2) ?
C4 C3 C2 . . 105.6(2) ?
C4 C3 H3 . . 127.2 ?
C2 C3 H3 . . 127.2 ?
N2 C4 C3 . . 106.6(2) ?
N2 C4 C5 . . 121.2(2) ?
C3 C4 C5 . . 132.2(2) ?
C4 C5 H5A . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C4 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
O4 C6 O3 . . 125.0(2) ?
O4 C6 C7 . . 118.0(2) ?
O3 C6 C7 . . 117.0(2) ?
C12 C7 C8 . . 119.3(2) ?
C12 C7 C6 . . 119.8(2) ?
C8 C7 C6 . . 120.8(2) ?
C9 C8 C7 . . 120.7(2) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C10 C9 C8 . . 118.4(2) ?
C10 C9 H9 . . 120.8 ?
C8 C9 H9 . . 120.8 ?
C9 C10 C11 . . 122.6(2) ?
C9 C10 N3 . . 119.2(2) ?
C11 C10 N3 . . 118.2(2) ?
C10 C11 C12 . . 118.3(2) ?
C10 C11 H11 . . 120.9 ?
C12 C11 H11 . . 120.9 ?
C11 C12 C7 . . 120.6(2) ?
C11 C12 H12 . . 119.7 ?
C7 C12 H12 . . 119.7 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O8 . 1.9344(17) y
Cu1 O7 . 1.9489(17) y
Cu1 N1 . 1.970(2) y
Cu1 O1 . 1.9811(16) y
Cu1 O3 . 2.3164(19) y
O1 C1 . 1.286(3) ?
O2 C1 . 1.236(3) ?
O3 C6 . 1.269(3) ?
O4 C6 . 1.244(3) ?
O5 N3 . 1.213(3) ?
O6 N3 . 1.216(3) ?
O7 H7A . 0.8468 ?
O7 H7B . 0.8446 ?
O8 H8A . 0.8503 ?
O8 H8B . 0.8496 ?
N1 C2 . 1.339(3) ?
N1 N2 . 1.345(3) ?
N2 C4 . 1.352(3) ?
N2 H2 . 0.8599 ?
N3 C10 . 1.475(3) ?
C1 C2 . 1.488(3) ?
C2 C3 . 1.387(3) ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.488(4) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.515(3) ?
C7 C12 . 1.388(4) ?
C7 C8 . 1.392(4) ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.376(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.378(4) ?
C11 C12 . 1.386(4) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O7 H7A O2 1_455 0.85 1.96 2.799(2) 172.6
O7 H7B O3 2_557 0.84 1.83 2.631(2) 156.8
O8 H8A O1 2_657 0.85 1.97 2.803(3) 165.3
O8 H8B O4 2_557 0.85 1.78 2.582(2) 155.9
N2 H2 O2 1_455 0.86 1.97 2.781(3) 156.5
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O8 Cu1 O1 C1 . . . . -165.77(18) ?
O7 Cu1 O1 C1 . . . . -74.7(4) ?
N1 Cu1 O1 C1 . . . . 5.10(18) ?
O3 Cu1 O1 C1 . . . . 100.61(18) ?
O8 Cu1 O3 C6 . . . . 167.18(17) ?
O7 Cu1 O3 C6 . . . . 75.23(18) ?
N1 Cu1 O3 C6 . . . . -22.18(18) ?
O1 Cu1 O3 C6 . . . . -103.75(17) ?
O8 Cu1 N1 C2 . . . . 40.1(4) ?
O7 Cu1 N1 C2 . . . . 165.23(17) ?
O1 Cu1 N1 C2 . . . . -2.40(17) ?
O3 Cu1 N1 C2 . . . . -96.07(17) ?
O8 Cu1 N1 N2 . . . . -140.9(3) ?
O7 Cu1 N1 N2 . . . . -15.8(3) ?
O1 Cu1 N1 N2 . . . . 176.6(3) ?
O3 Cu1 N1 N2 . . . . 82.9(3) ?
C2 N1 N2 C4 . . . . 0.3(3) ?
Cu1 N1 N2 C4 . . . . -178.7(2) ?
Cu1 O1 C1 O2 . . . . 173.2(2) ?
Cu1 O1 C1 C2 . . . . -6.5(3) ?
N2 N1 C2 C3 . . . . 0.1(3) ?
Cu1 N1 C2 C3 . . . . 179.42(17) ?
N2 N1 C2 C1 . . . . -179.5(2) ?
Cu1 N1 C2 C1 . . . . -0.2(3) ?
O2 C1 C2 N1 . . . . -175.2(2) ?
O1 C1 C2 N1 . . . . 4.5(3) ?
O2 C1 C2 C3 . . . . 5.2(5) ?
O1 C1 C2 C3 . . . . -175.1(3) ?
N1 C2 C3 C4 . . . . -0.4(3) ?
C1 C2 C3 C4 . . . . 179.1(3) ?
N1 N2 C4 C3 . . . . -0.5(3) ?
N1 N2 C4 C5 . . . . 179.1(2) ?
C2 C3 C4 N2 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . -179.1(3) ?
Cu1 O3 C6 O4 . . . . -100.5(3) ?
Cu1 O3 C6 C7 . . . . 78.9(2) ?
O4 C6 C7 C12 . . . . 25.6(4) ?
O3 C6 C7 C12 . . . . -153.8(2) ?
O4 C6 C7 C8 . . . . -156.2(3) ?
O3 C6 C7 C8 . . . . 24.3(4) ?
C12 C7 C8 C9 . . . . 0.5(4) ?
C6 C7 C8 C9 . . . . -177.7(2) ?
C7 C8 C9 C10 . . . . 0.9(4) ?
C8 C9 C10 C11 . . . . -1.4(4) ?
C8 C9 C10 N3 . . . . 177.5(3) ?
O5 N3 C10 C9 . . . . 175.5(3) ?
O6 N3 C10 C9 . . . . -4.0(4) ?
O5 N3 C10 C11 . . . . -5.5(4) ?
O6 N3 C10 C11 . . . . 174.9(3) ?
C9 C10 C11 C12 . . . . 0.4(4) ?
N3 C10 C11 C12 . . . . -178.4(3) ?
C10 C11 C12 C7 . . . . 1.0(4) ?
C8 C7 C12 C11 . . . . -1.4(4) ?
C6 C7 C12 C11 . . . . 176.7(3) ?
