#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/33/2223381.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_2223381
loop_
_publ_author_name
'Xu, Wen'
'Zhu, Da-Sheng'
'Song, Xiao-Dan'
'An, Zhe'
_publ_section_title
;Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]zinc(II)]
 dihydrate]
;
_journal_coeditor_code           HB5062
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1223
_journal_paper_doi               10.1107/S1600536809036939
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Zn (C14 H16 N5 O3)2], 2H2 O'
_chemical_formula_moiety         '(C28 H32 N10 O6 Zn), 2(H2 O)'
_chemical_formula_sum            'C28 H36 N10 O8 Zn'
_chemical_formula_weight         704.05
_chemical_name_systematic
;Poly[[bis[μ₂-8-ethyl-5-oxo-2-(piperazin-1-yl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylato]zinc(II)]
 dihydrate]
;
_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                 101.10(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.1146(12)
_cell_length_b                   21.424(4)
_cell_length_c                   12.577(3)
_cell_measurement_temperature    295(2)
_cell_volume                     1616.8(6)
_computing_cell_refinement       'RAPID-AUTO (Rigaku , 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15697
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.824
_exptl_absorpt_correction_T_max  0.866
_exptl_absorpt_correction_T_min  0.756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalStructure; Rigaku/MSC, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.831
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1254P)²+1.7801P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1577
_refine_ls_wR_factor_ref         0.2095
_reflns_number_gt                2570
_reflns_number_total             3684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            hb5062.cif
_cod_data_source_block           I
_cod_original_cell_volume        1616.9(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2223381
_cod_database_fobs_code          2223381
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_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
O O1W -0.045(3) -0.0632(10) -0.0746(11) 0.187(8) Uani d P 0.50 . .
O O2W 0.340(5) 0.0205(10) -0.0364(12) 0.251(14) Uani d P 0.50 . .
Zn Zn1 0.5000 0.0000 0.5000 0.0265(2) Uani d S 1 . .
O O1 0.6981(4) -0.00325(10) 0.3877(2) 0.0271(6) Uani d . 1 . .
O O2 0.8573(7) 0.01818(18) 0.2500(3) 0.0616(11) Uani d . 1 . .
O O3 0.3495(5) 0.07935(11) 0.4179(2) 0.0317(6) Uani d . 1 . .
N N1 0.4916(7) 0.17173(17) 0.1532(3) 0.0481(10) Uani d . 1 . .
N N2 0.2252(6) 0.24690(15) 0.1677(3) 0.0386(8) Uani d . 1 . .
N N3 -0.0127(6) 0.23572(16) 0.2988(3) 0.0436(9) Uani d . 1 . .
N N4 -0.0227(6) 0.32384(15) 0.1907(3) 0.0349(8) Uani d . 1 . .
N N5 -0.2450(5) 0.43908(14) 0.1084(2) 0.0273(7) Uani d D 1 . .
H H5N -0.154(8) 0.466(2) 0.152(4) 0.065(16) Uiso d D 1 . .
C C1 0.7147(7) 0.02891(17) 0.3064(3) 0.0316(8) Uani d . 1 . .
C C2 0.5658(7) 0.08450(17) 0.2772(3) 0.0317(8) Uani d . 1 . .
C C3 0.3947(6) 0.10453(16) 0.3346(3) 0.0271(7) Uani d . 1 . .
C C4 0.2744(7) 0.15974(16) 0.2910(3) 0.0303(8) Uani d . 1 . .
C C5 0.0937(8) 0.18359(19) 0.3318(3) 0.0398(10) Uani d . 1 . .
H H5 0.0454 0.1610 0.3861 0.048 Uiso calc R 1 . .
C C6 0.0671(7) 0.26762(18) 0.2197(3) 0.0327(8) Uani d . 1 . .
C C7 0.3246(7) 0.19340(18) 0.2034(3) 0.0360(9) Uani d . 1 . .
C C8 0.6010(8) 0.1189(2) 0.1902(4) 0.0457(11) Uani d . 1 . .
H H8 0.7096 0.1047 0.1535 0.055 Uiso calc R 1 . .
C C9 0.5540(11) 0.2051(3) 0.0585(5) 0.0665(16) Uani d . 1 . .
H H9B 0.5306 0.2496 0.0653 0.080 Uiso calc R 1 . .
H H9A 0.7107 0.1983 0.0582 0.080 Uiso calc R 1 . .
C C10 0.4247(16) 0.1834(5) -0.0401(7) 0.116(3) Uani d . 1 . .
H H10C 0.4566 0.1401 -0.0496 0.174 Uiso calc R 1 . .
H H10B 0.4605 0.2071 -0.0993 0.174 Uiso calc R 1 . .
H H10A 0.2693 0.1883 -0.0385 0.174 Uiso calc R 1 . .
C C11 -0.1608(8) 0.3572(2) 0.2553(4) 0.0475(11) Uani d . 1 . .
H H11B -0.0673 0.3839 0.3077 0.057 Uiso calc R 1 . .
H H11A -0.2346 0.3275 0.2947 0.057 Uiso calc R 1 . .
C C12 -0.3356(7) 0.3970(2) 0.1813(4) 0.0398(10) Uani d . 1 . .
H H12B -0.4429 0.3694 0.1379 0.048 Uiso calc R 1 . .
H H12A -0.4150 0.4218 0.2262 0.048 Uiso calc R 1 . .
C C13 -0.1090(6) 0.40176(17) 0.0469(3) 0.0317(8) Uani d . 1 . .
H H13A -0.0405 0.4295 0.0018 0.038 Uiso calc R 1 . .
H H13B -0.2057 0.3734 -0.0006 0.038 Uiso calc R 1 . .
C C14 0.0708(7) 0.36460(18) 0.1185(4) 0.0369(9) Uani d . 1 . .
H H14B 0.1500 0.3397 0.0737 0.044 Uiso calc R 1 . .
H H14A 0.1768 0.3929 0.1610 0.044 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Zn1 O1 . 3_656 180.0 ?
O1 Zn1 O3 . 3_656 92.90(10) ?
O1 Zn1 O3 3_656 3_656 87.10(10) ?
O1 Zn1 O3 . . 87.10(10) ?
O1 Zn1 O3 3_656 . 92.90(10) ?
O3 Zn1 O3 3_656 . 180.0 ?
O1 Zn1 N5 . 2_545 89.74(11) ?
O1 Zn1 N5 3_656 2_545 90.26(11) ?
O3 Zn1 N5 3_656 2_545 90.86(11) ?
O3 Zn1 N5 . 2_545 89.14(11) ?
O1 Zn1 N5 . 4_666 90.26(11) ?
O1 Zn1 N5 3_656 4_666 89.74(11) ?
O3 Zn1 N5 3_656 4_666 89.14(11) ?
O3 Zn1 N5 . 4_666 90.86(11) ?
N5 Zn1 N5 2_545 4_666 180.0 ?
C1 O1 Zn1 . . 134.5(2) ?
C3 O3 Zn1 . . 127.6(2) ?
C8 N1 C7 . . 119.0(3) ?
C8 N1 C9 . . 119.2(4) ?
C7 N1 C9 . . 121.8(4) ?
C7 N2 C6 . . 116.3(3) ?
C5 N3 C6 . . 115.3(4) ?
C6 N4 C14 . . 121.2(3) ?
C6 N4 C11 . . 122.4(3) ?
C14 N4 C11 . . 113.0(3) ?
C12 N5 C13 . . 108.3(3) ?
C12 N5 Zn1 . 2 115.4(2) ?
C13 N5 Zn1 . 2 112.8(2) ?
C12 N5 H5N . . 106(4) ?
C13 N5 H5N . . 108(4) ?
Zn1 N5 H5N 2 . 106(4) ?
O2 C1 O1 . . 122.6(4) ?
O2 C1 C2 . . 117.7(3) ?
O1 C1 C2 . . 119.7(3) ?
C8 C2 C3 . . 118.6(3) ?
C8 C2 C1 . . 116.2(3) ?
C3 C2 C1 . . 125.2(3) ?
O3 C3 C4 . . 119.4(3) ?
O3 C3 C2 . . 125.8(3) ?
C4 C3 C2 . . 114.7(3) ?
C7 C4 C5 . . 114.1(3) ?
C7 C4 C3 . . 123.2(4) ?
C5 C4 C3 . . 122.6(3) ?
N3 C5 C4 . . 124.7(4) ?
N3 C5 H5 . . 117.6 ?
C4 C5 H5 . . 117.6 ?
N2 C6 N4 . . 117.3(3) ?
N2 C6 N3 . . 125.3(4) ?
N4 C6 N3 . . 117.3(4) ?
N2 C7 N1 . . 117.6(3) ?
N2 C7 C4 . . 123.6(4) ?
N1 C7 C4 . . 118.7(3) ?
N1 C8 C2 . . 125.6(4) ?
N1 C8 H8 . . 117.2 ?
C2 C8 H8 . . 117.2 ?
C10 C9 N1 . . 110.8(7) ?
C10 C9 H9B . . 109.5 ?
N1 C9 H9B . . 109.5 ?
C10 C9 H9A . . 109.5 ?
N1 C9 H9A . . 109.5 ?
H9B C9 H9A . . 108.1 ?
C9 C10 H10C . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10C C10 H10B . . 109.5 ?
C9 C10 H10A . . 109.5 ?
H10C C10 H10A . . 109.5 ?
H10B C10 H10A . . 109.5 ?
N4 C11 C12 . . 110.0(3) ?
N4 C11 H11B . . 109.7 ?
C12 C11 H11B . . 109.7 ?
N4 C11 H11A . . 109.7 ?
C12 C11 H11A . . 109.7 ?
H11B C11 H11A . . 108.2 ?
N5 C12 C11 . . 114.7(3) ?
N5 C12 H12B . . 108.6 ?
C11 C12 H12B . . 108.6 ?
N5 C12 H12A . . 108.6 ?
C11 C12 H12A . . 108.6 ?
H12B C12 H12A . . 107.6 ?
N5 C13 C14 . . 113.1(3) ?
N5 C13 H13A . . 109.0 ?
C14 C13 H13A . . 109.0 ?
N5 C13 H13B . . 109.0 ?
C14 C13 H13B . . 109.0 ?
H13A C13 H13B . . 107.8 ?
N4 C14 C13 . . 111.2(3) ?
N4 C14 H14B . . 109.4 ?
C13 C14 H14B . . 109.4 ?
N4 C14 H14A . . 109.4 ?
C13 C14 H14A . . 109.4 ?
H14B C14 H14A . . 108.0 ?
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
Zn1 O1 . 2.031(3) y
Zn1 O1 3_656 2.031(3) ?
Zn1 O3 3_656 2.107(2) ?
Zn1 O3 . 2.107(2) y
Zn1 N5 2_545 2.275(3) ?
Zn1 N5 4_666 2.275(3) y
O1 C1 . 1.253(5) ?
O2 C1 . 1.247(5) ?
O3 C3 . 1.256(4) ?
N1 C8 . 1.351(5) ?
N1 C7 . 1.381(5) ?
N1 C9 . 1.500(6) ?
N2 C7 . 1.334(5) ?
N2 C6 . 1.343(5) ?
N3 C5 . 1.319(5) ?
N3 C6 . 1.373(5) ?
N4 C6 . 1.345(5) ?
N4 C14 . 1.454(5) ?
N4 C11 . 1.466(5) ?
N5 C12 . 1.468(5) ?
N5 C13 . 1.475(5) ?
N5 Zn1 2 2.275(3) ?
N5 H5N . 0.900(10) ?
C1 C2 . 1.501(5) ?
C2 C8 . 1.370(6) ?
C2 C3 . 1.446(5) ?
C3 C4 . 1.444(5) ?
C4 C7 . 1.399(5) ?
C4 C5 . 1.401(6) ?
C5 H5 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 C10 . 1.415(11) ?
C9 H9B . 0.9700 ?
C9 H9A . 0.9700 ?
C10 H10C . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10A . 0.9600 ?
C11 C12 . 1.534(5) ?
C11 H11B . 0.9700 ?
C11 H11A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 H12A . 0.9700 ?
C13 C14 . 1.508(5) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14B . 0.9700 ?
C14 H14A . 0.9700 ?
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
N5 H5N O2 2_655 0.91(5) 2.28(5) 3.168(5) 166(4)
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
O1 Zn1 O1 C1 3_656 . . . -50(2) ?
O3 Zn1 O1 C1 3_656 . . . 179.5(4) ?
O3 Zn1 O1 C1 . . . . -0.5(4) ?
N5 Zn1 O1 C1 2_545 . . . 88.7(4) ?
N5 Zn1 O1 C1 4_666 . . . -91.3(4) ?
O1 Zn1 O3 C3 . . . . 0.4(3) ?
O1 Zn1 O3 C3 3_656 . . . -179.6(3) ?
O3 Zn1 O3 C3 3_656 . . . 7E1(10) ?
N5 Zn1 O3 C3 2_545 . . . -89.4(3) ?
N5 Zn1 O3 C3 4_666 . . . 90.6(3) ?
Zn1 O1 C1 O2 . . . . 178.2(3) ?
Zn1 O1 C1 C2 . . . . 1.0(6) ?
O2 C1 C2 C8 . . . . -0.1(6) ?
O1 C1 C2 C8 . . . . 177.1(4) ?
O2 C1 C2 C3 . . . . -178.8(4) ?
O1 C1 C2 C3 . . . . -1.6(6) ?
Zn1 O3 C3 C4 . . . . -179.0(2) ?
Zn1 O3 C3 C2 . . . . -1.1(5) ?
C8 C2 C3 O3 . . . . -177.0(4) ?
C1 C2 C3 O3 . . . . 1.7(6) ?
C8 C2 C3 C4 . . . . 1.0(6) ?
C1 C2 C3 C4 . . . . 179.7(4) ?
O3 C3 C4 C7 . . . . 175.2(4) ?
C2 C3 C4 C7 . . . . -2.9(6) ?
O3 C3 C4 C5 . . . . -6.0(6) ?
C2 C3 C4 C5 . . . . 175.9(4) ?
C6 N3 C5 C4 . . . . -0.8(7) ?
C7 C4 C5 N3 . . . . -5.2(7) ?
C3 C4 C5 N3 . . . . 175.9(4) ?
C7 N2 C6 N4 . . . . 174.8(4) ?
C7 N2 C6 N3 . . . . -6.2(7) ?
C14 N4 C6 N2 . . . . -9.3(6) ?
C11 N4 C6 N2 . . . . -167.0(4) ?
C14 N4 C6 N3 . . . . 171.7(4) ?
C11 N4 C6 N3 . . . . 14.0(6) ?
C5 N3 C6 N2 . . . . 7.0(7) ?
C5 N3 C6 N4 . . . . -174.0(4) ?
C6 N2 C7 N1 . . . . -178.5(4) ?
C6 N2 C7 C4 . . . . -1.0(6) ?
C8 N1 C7 N2 . . . . 177.5(4) ?
C9 N1 C7 N2 . . . . -2.7(7) ?
C8 N1 C7 C4 . . . . -0.1(7) ?
C9 N1 C7 C4 . . . . 179.7(5) ?
C5 C4 C7 N2 . . . . 6.2(6) ?
C3 C4 C7 N2 . . . . -174.9(4) ?
C5 C4 C7 N1 . . . . -176.3(4) ?
C3 C4 C7 N1 . . . . 2.5(6) ?
C7 N1 C8 C2 . . . . -1.9(8) ?
C9 N1 C8 C2 . . . . 178.3(5) ?
C3 C2 C8 N1 . . . . 1.4(7) ?
C1 C2 C8 N1 . . . . -177.4(4) ?
C8 N1 C9 C10 . . . . 90.7(7) ?
C7 N1 C9 C10 . . . . -89.1(7) ?
C6 N4 C11 C12 . . . . -148.9(4) ?
C14 N4 C11 C12 . . . . 51.8(5) ?
C13 N5 C12 C11 . . . . 53.7(5) ?
Zn1 N5 C12 C11 2 . . . -178.8(3) ?
N4 C11 C12 N5 . . . . -52.7(5) ?
C12 N5 C13 C14 . . . . -55.0(4) ?
Zn1 N5 C13 C14 2 . . . 176.0(2) ?
C6 N4 C14 C13 . . . . 145.9(4) ?
C11 N4 C14 C13 . . . . -54.5(5) ?
N5 C13 C14 N4 . . . . 56.5(5) ?
