#------------------------------------------------------------------------------
#$Date: 2015-05-13 22:36:00 +0300 (Wed, 13 May 2015) $
#$Revision: 136357 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/99/2019933.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_2019933
loop_
_publ_author_name
'Yousefi, Zakieh'
'Eshtiagh-Hosseini, Hossein'
'Salimi, Alireza'
'Soleimannejad, Janet'
_publ_section_title
;
 (2-Aminopyrimidine-κN¹)aqua(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)copper(II):
 X-ray and DFT calculated structure
;
_journal_coeditor_code           FA3361
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              386
_journal_page_last               393
_journal_paper_doi               10.1107/S2053229615005331
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          '[Cu (C7 H3 N2 O4) (C4 H5 N2) (H2 O)]'
_chemical_formula_moiety         'C11 H10 Cu N4 O5'
_chemical_formula_sum            'C11 H10 Cu N4 O5'
_chemical_formula_weight         341.77
_chemical_name_systematic
(2-Aminopyrimidine-κN¹)aqua(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)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           SHELXL97
_cell_angle_alpha                80.980(4)
_cell_angle_beta                 87.261(4)
_cell_angle_gamma                64.488(5)
_cell_formula_units_Z            2
_cell_length_a                   7.4376(4)
_cell_length_b                   8.0321(4)
_cell_length_c                   11.4220(6)
_cell_measurement_reflns_used    4000
_cell_measurement_temperature    294.0(10)
_cell_measurement_theta_max      28.84
_cell_measurement_theta_min      2.84
_cell_volume                     608.05(6)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294.0(10)
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_device_type  'Agilent Xcalibur Eos'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8678
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.84
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.867
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             346
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.299
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0310
_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)+(0.0336P)²+0.2457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0744
_reflns_number_gt                2377
_reflns_number_total             2797
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3361sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        608.05(5)
_cod_database_code               2019933
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_symmetry_multiplicity
Cu Cu1 0.58382(4) 0.63364(4) 0.27226(2) 0.02800(10) Uani d . 1 1
N N1 0.4559(3) 0.4729(2) 0.26850(16) 0.0240(4) Uani d . 1 1
O O1 0.7374(2) 0.4895(2) 0.14170(15) 0.0368(4) Uani d . 1 1
O O2 0.7335(3) 0.2913(2) 0.02734(15) 0.0379(4) Uani d . 1 1
C C1 0.6719(3) 0.3808(3) 0.1090(2) 0.0274(5) Uani d . 1 1
C C2 0.5024(3) 0.3669(3) 0.18306(19) 0.0241(4) Uani d . 1 1
C C3 0.4001(4) 0.2635(3) 0.1699(2) 0.0328(5) Uani d . 1 1
H H3A 0.4314 0.1891 0.1104 0.039 Uiso calc R 1 1
C C4 0.2490(4) 0.2737(3) 0.2479(2) 0.0368(6) Uani d . 1 1
H H4A 0.1762 0.2065 0.2401 0.044 Uiso calc R 1 1
C C5 0.2041(3) 0.3827(3) 0.3377(2) 0.0319(5) Uani d . 1 1
H H5A 0.1036 0.3882 0.3908 0.038 Uiso calc R 1 1
C C6 0.3134(3) 0.4824(3) 0.34576(19) 0.0235(4) Uani d . 1 1
C C7 0.2921(3) 0.6128(3) 0.4336(2) 0.0266(5) Uani d . 1 1
O O3 0.3991(2) 0.7031(2) 0.40966(14) 0.0308(4) Uani d . 1 1
O O4 0.1818(2) 0.6234(2) 0.51765(15) 0.0377(4) Uani d . 1 1
N N11 0.7311(3) 0.7845(3) 0.29023(16) 0.0255(4) Uani d . 1 1
N N12 0.9146(3) 0.7348(3) 0.1188(2) 0.0397(5) Uani d . 1 1
H H12A 1.000(4) 0.751(4) 0.077(3) 0.040(8) Uiso d . 1 1
H H12B 0.868(4) 0.659(4) 0.105(3) 0.050(8) Uiso d . 1 1
C C12 0.8681(3) 0.8129(3) 0.2162(2) 0.0262(5) Uani d . 1 1
N N13 0.9603(3) 0.9186(3) 0.23718(18) 0.0321(4) Uani d . 1 1
C C14 0.9059(3) 1.0040(3) 0.3312(2) 0.0327(5) Uani d . 1 1
H H14A 0.9664 1.0790 0.3459 0.039 Uiso calc R 1 1
C C15 0.7651(3) 0.9885(3) 0.4086(2) 0.0337(5) Uani d . 1 1
H H15A 0.7270 1.0527 0.4733 0.040 Uiso calc R 1 1
C C16 0.6844(3) 0.8733(3) 0.3851(2) 0.0312(5) Uani d . 1 1
H H16A 0.5923 0.8555 0.4374 0.037 Uiso calc R 1 1
O O1W 0.3478(2) 0.8782(2) 0.14239(15) 0.0374(4) Uani d . 1 1
H H1W 0.2332 0.9035 0.1683 0.049 Uiso d R 1 1
H H2W 0.3575 0.8362 0.0818 0.049 Uiso d R 1 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
N1 Cu1 N11 174.43(8)
N1 Cu1 O3 80.07(7)
N11 Cu1 O3 98.26(7)
N1 Cu1 O1 79.79(7)
N11 Cu1 O1 101.38(7)
O3 Cu1 O1 159.40(6)
N1 Cu1 O1W 93.49(7)
N11 Cu1 O1W 91.85(7)
O3 Cu1 O1W 91.03(6)
O1 Cu1 O1W 94.48(7)
C6 N1 C2 122.75(18)
C6 N1 Cu1 118.48(14)
C2 N1 Cu1 118.55(14)
C1 O1 Cu1 115.47(14)
O2 C1 O1 126.1(2)
O2 C1 C2 119.90(19)
O1 C1 C2 113.96(18)
N1 C2 C3 120.5(2)
N1 C2 C1 111.58(17)
C3 C2 C1 127.9(2)
C2 C3 C4 117.8(2)
C2 C3 H3A 121.1
C4 C3 H3A 121.1
C3 C4 C5 121.1(2)
C3 C4 H4A 119.4
C5 C4 H4A 119.4
C6 C5 C4 117.9(2)
C6 C5 H5A 121.1
C4 C5 H5A 121.1
N1 C6 C5 120.0(2)
N1 C6 C7 111.80(17)
C5 C6 C7 128.22(19)
O4 C7 O3 126.3(2)
O4 C7 C6 120.16(19)
O3 C7 C6 113.59(18)
C7 O3 Cu1 115.69(14)
C16 N11 C12 116.53(18)
C16 N11 Cu1 115.40(14)
C12 N11 Cu1 128.03(15)
C12 N12 H12A 117.5(19)
C12 N12 H12B 121(2)
H12A N12 H12B 121(3)
N12 C12 N13 117.5(2)
N12 C12 N11 119.3(2)
N13 C12 N11 123.2(2)
C14 N13 C12 117.3(2)
N13 C14 C15 123.6(2)
N13 C14 H14A 118.2
C15 C14 H14A 118.2
C16 C15 C14 116.0(2)
C16 C15 H15A 122.0
C14 C15 H15A 122.0
N11 C16 C15 123.3(2)
N11 C16 H16A 118.4
C15 C16 H16A 118.4
Cu1 O1W H1W 109.7
Cu1 O1W H2W 104.5
H1W O1W H2W 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 N1 1.9112(17)
Cu1 N11 1.9880(17)
Cu1 O3 2.0175(15)
Cu1 O1 2.0267(16)
Cu1 O1W 2.3465(17)
N1 C6 1.331(3)
N1 C2 1.331(3)
O1 C1 1.275(3)
O2 C1 1.218(3)
C1 C2 1.519(3)
C2 C3 1.374(3)
C3 C4 1.383(3)
C3 H3A 0.9300
C4 C5 1.388(3)
C4 H4A 0.9300
C5 C6 1.379(3)
C5 H5A 0.9300
C6 C7 1.516(3)
C7 O4 1.222(3)
C7 O3 1.284(3)
N11 C16 1.340(3)
N11 C12 1.365(3)
N12 C12 1.321(3)
N12 H12A 0.82(3)
N12 H12B 0.85(3)
C12 N13 1.352(3)
N13 C14 1.319(3)
C14 C15 1.372(3)
C14 H14A 0.9300
C15 C16 1.364(3)
C15 H15A 0.9300
C16 H16A 0.9300
O1W H1W 0.8368
O1W H2W 0.8029
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
N12 H12A O2 2_765 0.82(3) 2.19(3) 2.984(3) 164(3)
N12 H12B O1 . 0.85(3) 1.98(3) 2.780(3) 157(3)
O1W H1W N13 1_455 0.84 2.10 2.931(2) 170.4
O1W H2W O2 2_665 0.80 2.03 2.761(2) 150.4

_cod_database_fobs_code 2019933
