#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/74/2217455.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_2217455
loop_
_publ_author_name
'Yuan-Hui Wu'
'Tian-Mo Liu'
'Su-Xing Luo'
_publ_section_title
;
 Diaquabis(5-phenyl-1H-pyrazole-3-carboxylato)copper(II)
;
_journal_coeditor_code           CI2551
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m355
_journal_page_last               m355
_journal_paper_doi               10.1107/S1600536808000810
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C10 H7 N2 O2)2 (H2 O)2]'
_chemical_formula_moiety         'C20 H18 Cu N4 O6'
_chemical_formula_sum            'C20 H18 Cu N4 O6'
_chemical_formula_weight         473.92
_chemical_name_systematic
;
Diaquabis(5-phenyl-1H-pyrazole-3-carboxylato)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 106.2930(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.0443(6)
_cell_length_b                   32.161(4)
_cell_length_c                   6.3234(8)
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      26.60
_cell_measurement_theta_min      2.53
_cell_volume                     984.6(2)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8611
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.53
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.157
_exptl_absorpt_correction_T_max  0.8285
_exptl_absorpt_correction_T_min  0.6897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.318
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2254
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0302P)²+0.72P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0838
_reflns_number_gt                1907
_reflns_number_total             2254
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci2551.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2217455
_cod_database_fobs_code          2217455
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
Cu Cu1 0.5000 0.0000 0.0000 0.03166(13) Uani d S 1
O O1 0.3462(3) 0.01796(5) 0.2440(2) 0.0325(3) Uani d . 1
O O2 0.3301(4) 0.07235(5) 0.4604(3) 0.0404(4) Uani d . 1
O O3 0.0850(4) 0.03336(6) -0.2706(3) 0.0380(4) Uani d D 1
N N1 0.6670(4) 0.05536(5) 0.0513(3) 0.0294(4) Uani d . 1
N N2 0.8212(4) 0.08034(5) -0.0348(3) 0.0301(4) Uani d . 1
H H2 0.8956 0.0730 -0.1359 0.036 Uiso calc R 1
C C1 0.4084(4) 0.05525(7) 0.3144(3) 0.0288(5) Uani d . 1
C C2 0.5895(4) 0.07783(7) 0.2015(3) 0.0277(4) Uani d . 1
C C3 0.6964(4) 0.11779(7) 0.2111(4) 0.0302(5) Uani d . 1
H H3 0.6732 0.1395 0.3017 0.036 Uiso calc R 1
C C4 0.8454(4) 0.11852(6) 0.0569(4) 0.0282(4) Uani d . 1
C C5 1.0091(5) 0.15138(7) -0.0085(4) 0.0328(5) Uani d . 1
C C6 1.0740(6) 0.18727(8) 0.1155(5) 0.0473(6) Uani d . 1
H H6 1.0067 0.1911 0.2368 0.057 Uiso calc R 1
C C7 1.2389(7) 0.21770(9) 0.0605(6) 0.0641(9) Uani d . 1
H H7 1.2821 0.2417 0.1454 0.077 Uiso calc R 1
C C8 1.3376(6) 0.21240(9) -0.1183(6) 0.0642(9) Uani d . 1
H H8 1.4482 0.2328 -0.1543 0.077 Uiso calc R 1
C C9 1.2744(6) 0.17720(10) -0.2448(5) 0.0565(8) Uani d . 1
H H9 1.3419 0.1738 -0.3663 0.068 Uiso calc R 1
C C10 1.1097(5) 0.14664(8) -0.1918(4) 0.0438(6) Uani d . 1
H H10 1.0662 0.1229 -0.2786 0.053 Uiso calc R 1
H H1W 0.138(6) 0.0417(9) -0.376(4) 0.069(10) Uiso d D 1
H H2W -0.041(5) 0.0163(8) -0.312(5) 0.075(11) Uiso d D 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
N1 Cu1 N1 . 3_655 180 y
N1 Cu1 O1 . 3_655 98.56(6) y
N1 Cu1 O1 3_655 3_655 81.44(6) ?
N1 Cu1 O1 . . 81.44(6) y
N1 Cu1 O1 3_655 . 98.56(6) ?
O1 Cu1 O1 3_655 . 180 y
N1 Cu1 O3 . . 87.85(7) y
N1 Cu1 O3 3_655 . 92.15(7) y
O1 Cu1 O3 3_655 . 91.56(6) y
O1 Cu1 O3 . . 88.44(6) y
C1 O1 Cu1 . . 115.29(13) ?
Cu1 O3 H1W . . 107(2) ?
Cu1 O3 H2W . . 110(2) ?
H1W O3 H2W . . 111(2) ?
C2 N1 N2 . . 106.51(17) ?
C2 N1 Cu1 . . 114.33(14) ?
N2 N1 Cu1 . . 138.77(14) ?
N1 N2 C4 . . 111.41(17) ?
N1 N2 H2 . . 124.3 ?
C4 N2 H2 . . 124.3 ?
O2 C1 O1 . . 125.27(19) ?
O2 C1 C2 . . 120.58(19) ?
O1 C1 C2 . . 114.14(18) ?
N1 C2 C3 . . 110.16(18) ?
N1 C2 C1 . . 114.60(18) ?
C3 C2 C1 . . 135.23(19) ?
C4 C3 C2 . . 105.36(19) ?
C4 C3 H3 . . 127.3 ?
C2 C3 H3 . . 127.3 ?
N2 C4 C3 . . 106.56(18) ?
N2 C4 C5 . . 121.60(19) ?
C3 C4 C5 . . 131.8(2) ?
C6 C5 C10 . . 118.6(2) ?
C6 C5 C4 . . 120.2(2) ?
C10 C5 C4 . . 121.2(2) ?
C5 C6 C7 . . 120.6(3) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C8 C7 C6 . . 120.1(3) ?
C8 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C7 C8 C9 . . 120.4(3) ?
C7 C8 H8 . . 119.8 ?
C9 C8 H8 . . 119.8 ?
C8 C9 C10 . . 120.1(3) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C9 C10 C5 . . 120.3(3) ?
C9 C10 H10 . . 119.9 ?
C5 C10 H10 . . 119.9 ?
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 N1 . 1.9572(17) y
Cu1 N1 3_655 1.9573(17) ?
Cu1 O1 3_655 1.9968(14) ?
Cu1 O1 . 1.9968(14) y
Cu1 O3 . 2.5400(19) y
O1 C1 . 1.287(3) ?
O2 C1 . 1.231(3) ?
O3 H1W . 0.827(10) ?
O3 H2W . 0.825(10) ?
N1 C2 . 1.336(3) ?
N1 N2 . 1.336(2) ?
N2 C4 . 1.349(3) ?
N2 H2 . 0.86 ?
C1 C2 . 1.496(3) ?
C2 C3 . 1.388(3) ?
C3 C4 . 1.388(3) ?
C3 H3 . 0.93 ?
C4 C5 . 1.470(3) ?
C5 C6 . 1.382(3) ?
C5 C10 . 1.398(3) ?
C6 C7 . 1.390(4) ?
C6 H6 . 0.93 ?
C7 C8 . 1.368(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.371(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.387(3) ?
C9 H9 . 0.93 ?
C10 H10 . 0.93 ?
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
O3 H1W O2 1_554 0.83(3) 1.88(3) 2.679(3) 161(3)
N2 H2 O3 1_655 0.86 1.93 2.719(3) 152
O3 H2W O1 3_555 0.83(3) 2.04(3) 2.773(3) 149(3)
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
N1 Cu1 O1 C1 . 2.75(15)
N1 Cu1 O1 C1 3_655 -177.25(15)
O3 Cu1 O1 C1 . -85.31(15)
O1 Cu1 N1 C2 3_655 175.94(15)
O1 Cu1 N1 C2 . -4.06(15)
O3 Cu1 N1 C2 . 84.69(16)
O1 Cu1 N1 N2 3_655 4.4(2)
O1 Cu1 N1 N2 . -175.6(2)
O3 Cu1 N1 N2 . -86.8(2)
C2 N1 N2 C4 . 0.1(2)
Cu1 N1 N2 C4 . 172.02(17)
Cu1 O1 C1 O2 . 178.61(18)
Cu1 O1 C1 C2 . -1.0(2)
N2 N1 C2 C3 . 0.0(2)
Cu1 N1 C2 C3 . -174.22(15)
N2 N1 C2 C1 . 178.84(17)
Cu1 N1 C2 C1 . 4.7(2)
O2 C1 C2 N1 . 178.0(2)
O1 C1 C2 N1 . -2.4(3)
O2 C1 C2 C3 . -3.5(4)
O1 C1 C2 C3 . 176.1(2)
N1 C2 C3 C4 . 0.0(2)
C1 C2 C3 C4 . -178.6(2)
N1 N2 C4 C3 . -0.1(2)
N1 N2 C4 C5 . 179.06(19)
C2 C3 C4 N2 . 0.1(2)
C2 C3 C4 C5 . -179.0(2)
N2 C4 C5 C6 . -167.6(2)
C3 C4 C5 C6 . 11.3(4)
N2 C4 C5 C10 . 10.3(3)
C3 C4 C5 C10 . -170.8(2)
C10 C5 C6 C7 . -0.8(4)
C4 C5 C6 C7 . 177.2(3)
C5 C6 C7 C8 . 0.3(5)
C6 C7 C8 C9 . 0.2(5)
C7 C8 C9 C10 . -0.1(5)
C8 C9 C10 C5 . -0.5(4)
C6 C5 C10 C9 . 0.9(4)
C4 C5 C10 C9 . -177.1(2)
