#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/27/2202772.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_2202772
loop_
_publ_author_name
'Li, Xing'
'Bi, Wenhua'
'Yuan, Daqiang'
'Cao, Rong'
_publ_section_title
;Diaqua(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylato-κN³)(1,10-phenanthroline)zinc(II)
 dihydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m470
_journal_page_last               m472
_journal_paper_doi               10.1107/S1600536803012819
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac
'[Zn (C5 H2 N2 O4) (C12 H8 N2) (H2 O)2], 2H2 O'
_chemical_formula_moiety         'C17 H14 N4 O6 Zn, 2H2 O'
_chemical_formula_sum            'C17 H18 N4 O8 Zn'
_chemical_formula_weight         471.72
_chemical_name_systematic
;
Diaqua(2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylato-\kN³)(1,10-
phenanthroline)zinc(II) dihydrate
;
_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                91.834(2)
_cell_angle_beta                 94.264(2)
_cell_angle_gamma                111.9150(10)
_cell_formula_units_Z            2
_cell_length_a                   7.9351(6)
_cell_length_b                   10.1874(8)
_cell_length_c                   12.6841(10)
_cell_measurement_reflns_used    2440
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.06
_cell_measurement_theta_min      1.61
_cell_volume                     946.65(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        'SAINT (Siemens, 1994)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Siemens, 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Siemens 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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0570
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4875
_diffrn_reflns_theta_full        25.06
_diffrn_reflns_theta_max         25.06
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    1.353
_exptl_absorpt_correction_T_max  0.850
_exptl_absorpt_correction_T_min  0.593
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             484
_exptl_crystal_size_max          .26
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .12
_refine_diff_density_max         0.727
_refine_diff_density_min         -0.802
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     303
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.055
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0626P)²+4.4071P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1658
_reflns_number_gt                2680
_reflns_number_total             3303
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6249.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2202772
_cod_database_fobs_code          2202772
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Zn -0.32324(9) -0.21650(7) 0.26949(6) 0.0317(2) Uani d . 1 . . Zn
O1 -0.5194(5) -0.1362(4) 0.3062(3) 0.0357(10) Uani d . 1 . . O
O2 -0.8075(6) -0.1972(4) 0.3424(4) 0.0399(11) Uani d . 1 . . O
O3 -0.9297(6) -0.6982(5) 0.4624(4) 0.0464(12) Uani d . 1 . . O
O4 -0.3755(6) -0.5488(5) 0.3340(4) 0.0427(11) Uani d . 1 . . O
O5 -0.1475(7) -0.3258(5) 0.2432(4) 0.0386(11) Uani d . 1 . . O
O6 -0.1640(7) -0.1179(5) 0.4107(4) 0.0373(11) Uani d . 1 . . O
O7 -0.3003(9) -0.7889(7) 0.3779(6) 0.0682(18) Uani d . 1 . . O
O8 -0.3453(9) -0.0914(6) 0.5807(4) 0.0489(13) Uani d . 1 . . O
N1 -0.5197(6) -0.3929(5) 0.3323(4) 0.0291(11) Uani d . 1 . . N
N2 -0.6549(6) -0.6195(5) 0.3959(4) 0.0325(11) Uani d . 1 . . N
H2A -0.6466 -0.7015 0.4081 0.039 Uiso calc R 1 . . H
N3 -0.4592(7) -0.2757(5) 0.1055(4) 0.0352(12) Uani d . 1 . . N
N4 -0.1784(7) -0.0371(5) 0.1839(4) 0.0342(12) Uani d . 1 . . N
C1 -0.6680(8) -0.2238(6) 0.3328(5) 0.0311(13) Uani d . 1 . . C
C2 -0.6728(8) -0.3719(6) 0.3556(4) 0.0279(12) Uani d . 1 . . C
C3 -0.8166(8) -0.4666(6) 0.3974(5) 0.0339(14) Uani d . 1 . . C
H3A -0.9193 -0.4442 0.4109 0.041 Uiso calc R 1 . . H
C4 -0.8119(8) -0.6014(7) 0.4210(5) 0.0338(14) Uani d . 1 . . C
C5 -0.5108(8) -0.5197(6) 0.3533(5) 0.0310(13) Uani d . 1 . . C
C6 -0.5972(10) -0.3906(8) 0.0691(6) 0.0497(18) Uani d . 1 . . C
H6A -0.6419 -0.4653 0.1151 0.060 Uiso calc R 1 . . H
C7 -0.6820(12) -0.4092(9) -0.0336(6) 0.060(2) Uani d . 1 . . C
H7A -0.7821 -0.4943 -0.0564 0.072 Uiso calc R 1 . . H
C8 -0.6193(11) -0.3041(9) -0.1000(6) 0.058(2) Uani d . 1 . . C
H8A -0.6764 -0.3148 -0.1700 0.070 Uiso calc R 1 . . H
C9 -0.4694(10) -0.1788(8) -0.0658(5) 0.0437(16) Uani d . 1 . . C
C10 -0.3950(12) -0.0629(9) -0.1293(6) 0.057(2) Uani d . 1 . . C
H10A -0.4479 -0.0683 -0.1998 0.069 Uiso calc R 1 . . H
C11 -0.2522(12) 0.0544(9) -0.0932(6) 0.056(2) Uani d . 1 . . C
H11A -0.2040 0.1291 -0.1386 0.067 Uiso calc R 1 . . H
C12 -0.1707(10) 0.0679(8) 0.0148(5) 0.0436(16) Uani d . 1 . . C
C13 -0.0229(11) 0.1875(8) 0.0577(6) 0.055(2) Uani d . 1 . . C
H13A 0.0334 0.2639 0.0150 0.066 Uiso calc R 1 . . H
C14 0.0388(10) 0.1932(8) 0.1598(7) 0.055(2) Uani d . 1 . . C
H14A 0.1376 0.2750 0.1899 0.066 Uiso calc R 1 . . H
C15 -0.0415(9) 0.0795(7) 0.2225(6) 0.0462(17) Uani d . 1 . . C
H15A 0.0036 0.0864 0.2948 0.055 Uiso calc R 1 . . H
C16 -0.2434(8) -0.0420(7) 0.0802(5) 0.0335(14) Uani d . 1 . . C
C17 -0.3939(9) -0.1699(7) 0.0401(5) 0.0363(14) Uani d . 1 . . C
H5A -0.046(10) -0.282(7) 0.284(6) 0.04(2) Uiso d . 1 . . H
H5B -0.205(10) -0.400(8) 0.273(6) 0.05(2) Uiso d . 1 . . H
H6B -0.120(12) -0.160(9) 0.438(7) 0.07(3) Uiso d . 1 . . H
H6C -0.228(13) -0.096(10) 0.461(8) 0.09(3) Uiso d . 1 . . H
H7B -0.309(13) -0.705(11) 0.379(7) 0.08(3) Uiso d . 1 . . H
H7C -0.210(13) -0.771(10) 0.409(7) 0.08(3) Uiso d . 1 . . H
H8B -0.477(15) -0.099(10) 0.593(8) 0.10(3) Uiso d . 1 . . H
H8C -0.300(10) -0.022(7) 0.603(5) 0.03(2) Uiso d . 1 . . H
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'
Zn Zn 0.2839 1.4301 '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_publ_flag
O1 Zn O6 90.1(2) y
O1 Zn N1 78.07(16) y
O6 Zn N1 99.13(19) y
O1 Zn O5 171.39(18) y
O6 Zn O5 90.4(2) y
N1 Zn O5 93.37(19) y
O1 Zn N4 93.25(17) y
O6 Zn N4 90.89(19) y
N1 Zn N4 166.67(18) y
O5 Zn N4 95.33(19) y
O1 Zn N3 89.30(18) y
O6 Zn N3 167.46(19) y
N1 Zn N3 93.00(18) y
O5 Zn N3 92.01(19) y
N4 Zn N3 76.64(19) y
C1 O1 Zn 116.9(4) ?
Zn O5 H5B 97(5) ?
Zn O5 H5A 107(5) ?
H5B O5 H5A 106(7) ?
Zn O6 H6C 114(6) ?
Zn O6 H6B 115(7) ?
H6C O6 H6B 104(9) ?
H7C O7 H7B 101(9) ?
H8C O8 H8B 97(8) ?
C5 N1 C2 117.2(5) ?
C5 N1 Zn 128.8(4) ?
C2 N1 Zn 114.1(4) ?
C5 N2 C4 125.4(5) ?
C5 N2 H2A 117.3 ?
C4 N2 H2A 117.3 ?
C6 N3 C17 118.5(6) ?
C6 N3 Zn 129.1(5) ?
C17 N3 Zn 112.2(4) ?
C15 N4 C16 117.5(5) ?
C15 N4 Zn 126.8(4) ?
C16 N4 Zn 115.5(4) ?
O2 C1 O1 124.6(5) ?
O2 C1 C2 118.9(5) ?
O1 C1 C2 116.5(5) ?
C3 C2 N1 125.7(5) ?
C3 C2 C1 120.8(5) ?
N1 C2 C1 113.5(5) ?
C2 C3 C4 118.7(6) ?
C2 C3 H3A 120.6 ?
C4 C3 H3A 120.6 ?
O3 C4 N2 119.1(6) ?
O3 C4 C3 126.8(6) ?
N2 C4 C3 114.1(5) ?
O4 C5 N1 121.7(5) ?
O4 C5 N2 119.4(5) ?
N1 C5 N2 118.9(5) ?
N3 C6 C7 123.5(7) ?
N3 C6 H6A 118.2 ?
C7 C6 H6A 118.2 ?
C8 C7 C6 118.9(7) ?
C8 C7 H7A 120.6 ?
C6 C7 H7A 120.6 ?
C7 C8 C9 120.2(7) ?
C7 C8 H8A 119.9 ?
C9 C8 H8A 119.9 ?
C8 C9 C17 116.5(6) ?
C8 C9 C10 124.3(7) ?
C17 C9 C10 119.2(7) ?
C11 C10 C9 122.1(7) ?
C11 C10 H10A 119.0 ?
C9 C10 H10A 119.0 ?
C10 C11 C12 120.5(6) ?
C10 C11 H11A 119.7 ?
C12 C11 H11A 119.7 ?
C16 C12 C13 117.6(6) ?
C16 C12 C11 118.9(7) ?
C13 C12 C11 123.4(6) ?
C14 C13 C12 119.3(6) ?
C14 C13 H13A 120.3 ?
C12 C13 H13A 120.3 ?
C13 C14 C15 120.5(7) ?
C13 C14 H14A 119.7 ?
C15 C14 H14A 119.7 ?
N4 C15 C14 121.9(7) ?
N4 C15 H15A 119.0 ?
C14 C15 H15A 119.0 ?
N4 C16 C12 123.0(6) ?
N4 C16 C17 116.5(5) ?
C12 C16 C17 120.4(6) ?
N3 C17 C9 122.4(6) ?
N3 C17 C16 118.8(5) ?
C9 C17 C16 118.8(6) ?
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
Zn O1 . 2.084(4) y
Zn O6 . 2.101(5) y
Zn N1 . 2.116(5) y
Zn O5 . 2.122(5) y
Zn N4 . 2.140(5) y
Zn N3 . 2.226(5) y
O1 C1 . 1.263(7) ?
O2 C1 . 1.247(7) ?
O3 C4 . 1.241(7) ?
O4 C5 . 1.253(7) ?
O5 H5B . 0.84(8) ?
O5 H5A . 0.88(8) ?
O6 H6C . 0.92(10) ?
O6 H6B . 0.73(9) ?
O7 H7C . 0.75(10) ?
O7 H7B . 0.89(10) ?
O8 H8C . 0.70(7) ?
O8 H8B . 1.04(11) ?
N1 C5 . 1.354(7) ?
N1 C2 . 1.361(7) ?
N2 C5 . 1.375(7) ?
N2 C4 . 1.382(8) ?
N2 H2A . 0.8800 ?
N3 C6 . 1.310(8) ?
N3 C17 . 1.350(8) ?
N4 C15 . 1.324(8) ?
N4 C16 . 1.370(8) ?
C1 C2 . 1.533(8) ?
C2 C3 . 1.347(8) ?
C3 C4 . 1.428(8) ?
C3 H3A . 0.9500 ?
C6 C7 . 1.393(10) ?
C6 H6A . 0.9500 ?
C7 C8 . 1.352(11) ?
C7 H7A . 0.9500 ?
C8 C9 . 1.410(11) ?
C8 H8A . 0.9500 ?
C9 C17 . 1.416(9) ?
C9 C10 . 1.416(10) ?
C10 C11 . 1.341(11) ?
C10 H10A . 0.9500 ?
C11 C12 . 1.450(10) ?
C11 H11A . 0.9500 ?
C12 C16 . 1.387(9) ?
C12 C13 . 1.397(11) ?
C13 C14 . 1.342(11) ?
C13 H13A . 0.9500 ?
C14 C15 . 1.401(10) ?
C14 H14A . 0.9500 ?
C15 H15A . 0.9500 ?
C16 C17 . 1.445(9) ?
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
N2 H2A O8 2_446 0.88 2.10 2.971(5) 172
O5 H5A O2 1_655 0.88(8) 1.85(8) 2.708(7) 166(7)
O5 H5B O4 1_555 0.84(8) 1.85(8) 2.678(7) 167(9)
O6 H6B O3 2_446 0.73(10) 2.08(9) 2.776(7) 162(10)
O6 H6C O8 1_555 0.92(11) 1.85(11) 2.741(9) 164(9)
O7 H7B O4 1_555 0.89(10) 1.94(11) 2.789(9) 160(10)
O7 H7C O3 1_655 0.75(10) 2.11(10) 2.844(9) 166(8)
O8 H8B O7 2_446 1.04(13) 1.79(12) 2.715(10) 146(8)
O8 H8C O2 2_456 0.70(7) 2.14(7) 2.836(7) 171(9)
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
O6 Zn O1 C1 -108.5(4)
N1 Zn O1 C1 -9.2(4)
O5 Zn O1 C1 -14.9(14)
N4 Zn O1 C1 160.6(4)
N3 Zn O1 C1 84.0(4)
O1 Zn N1 C5 -173.8(5)
O6 Zn N1 C5 -85.7(5)
O5 Zn N1 C5 5.3(5)
N4 Zn N1 C5 136.0(8)
N3 Zn N1 C5 97.5(5)
O1 Zn N1 C2 4.9(4)
O6 Zn N1 C2 93.1(4)
O5 Zn N1 C2 -176.0(4)
N4 Zn N1 C2 -45.3(10)
N3 Zn N1 C2 -83.8(4)
O1 Zn N3 C6 -85.2(6)
O6 Zn N3 C6 -172.7(9)
N1 Zn N3 C6 -7.2(6)
O5 Zn N3 C6 86.3(6)
N4 Zn N3 C6 -178.7(6)
O1 Zn N3 C17 89.3(4)
O6 Zn N3 C17 1.8(12)
N1 Zn N3 C17 167.3(4)
O5 Zn N3 C17 -99.2(4)
N4 Zn N3 C17 -4.2(4)
O1 Zn N4 C15 91.3(6)
O6 Zn N4 C15 1.1(6)
N1 Zn N4 C15 140.1(8)
O5 Zn N4 C15 -89.4(6)
N3 Zn N4 C15 179.8(6)
O1 Zn N4 C16 -84.5(4)
O6 Zn N4 C16 -174.7(4)
N1 Zn N4 C16 -35.7(11)
O5 Zn N4 C16 94.8(4)
N3 Zn N4 C16 4.0(4)
Zn O1 C1 O2 -169.3(5)
Zn O1 C1 C2 11.5(7)
C5 N1 C2 C3 -0.3(9)
Zn N1 C2 C3 -179.2(5)
C5 N1 C2 C1 178.0(5)
Zn N1 C2 C1 -0.9(6)
O2 C1 C2 C3 -7.8(9)
O1 C1 C2 C3 171.5(6)
O2 C1 C2 N1 173.8(5)
O1 C1 C2 N1 -7.0(8)
N1 C2 C3 C4 0.5(9)
C1 C2 C3 C4 -177.7(5)
C5 N2 C4 O3 -177.6(6)
C5 N2 C4 C3 0.9(9)
C2 C3 C4 O3 177.6(6)
C2 C3 C4 N2 -0.8(8)
C2 N1 C5 O4 179.7(5)
Zn N1 C5 O4 -1.6(9)
C2 N1 C5 N2 0.4(8)
Zn N1 C5 N2 179.1(4)
C4 N2 C5 O4 179.9(6)
C4 N2 C5 N1 -0.8(9)
C17 N3 C6 C7 -0.7(11)
Zn N3 C6 C7 173.4(6)
N3 C6 C7 C8 0.3(13)
C6 C7 C8 C9 0.7(12)
C7 C8 C9 C17 -1.1(11)
C7 C8 C9 C10 -179.6(8)
C8 C9 C10 C11 179.9(7)
C17 C9 C10 C11 1.5(11)
C9 C10 C11 C12 -1.6(12)
C10 C11 C12 C16 -0.3(11)
C10 C11 C12 C13 -179.5(7)
C16 C12 C13 C14 -2.0(11)
C11 C12 C13 C14 177.2(7)
C12 C13 C14 C15 1.3(12)
C16 N4 C15 C14 -1.7(10)
Zn N4 C15 C14 -177.4(5)
C13 C14 C15 N4 0.6(12)
C15 N4 C16 C12 0.9(9)
Zn N4 C16 C12 177.1(5)
C15 N4 C16 C17 -179.5(6)
Zn N4 C16 C17 -3.3(7)
C13 C12 C16 N4 1.0(10)
C11 C12 C16 N4 -178.3(6)
C13 C12 C16 C17 -178.7(6)
C11 C12 C16 C17 2.1(9)
C6 N3 C17 C9 0.3(10)
Zn N3 C17 C9 -174.8(5)
C6 N3 C17 C16 179.1(6)
Zn N3 C17 C16 4.0(7)
C8 C9 C17 N3 0.6(10)
C10 C9 C17 N3 179.2(6)
C8 C9 C17 C16 -178.2(6)
C10 C9 C17 C16 0.3(9)
N4 C16 C17 N3 -0.7(8)
C12 C16 C17 N3 179.0(6)
N4 C16 C17 C9 178.2(5)
C12 C16 C17 C9 -2.1(9)
