#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/21/8102102.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8102102
loop_
_publ_author_name
'An, Z.'
'Cui, R.-H.'
'Wang, R.-S.'
_publ_section_title
;
Crystal structure of poly(bis(1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-
(1-piperazinyl)-1,8-naphtyridine-3-carboxylato)-zinc(II)) dihydrate, 
Zn(C₁₅H₁₆FN₄O₃)₂ · 2H₂O
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              135
_journal_page_last               136
_journal_volume                  222
_journal_year                    2007
_chemical_formula_moiety         'C30 H32 F2 N8 O6 Zn, 2(H2 O)'
_chemical_formula_structural     'Zn(C15H16FN4O3)2 &#x00B7; 2H2O'
_chemical_formula_sum            'C30 H32 F2 N8 O8 Zn'
_chemical_formula_weight         736.01
_chemical_name_systematic
; 
poly(bis(1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-
(1-piperazinyl)-1,8-naphtyridine-3-carboxylato)zinc(II))
;
_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                90.000(5)
_cell_angle_beta                 100.379(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   5.939(5)
_cell_length_b                   21.462(5)
_cell_length_c                   13.195(5)
_cell_measurement_reflns_used    7899
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.09
_cell_measurement_theta_min      1.84
_cell_volume                     1654.4(16)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1998)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       omega
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8267
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  0.8944
_exptl_absorpt_correction_T_min  0.7920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0428
_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)+(0.0717P)²+0.8778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1247
_refine_ls_wR_factor_ref         0.1332
_reflns_number_gt                2342
_reflns_number_total             2933
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-1980.cff
_cod_data_source_block           Zn-enox
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102102
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.0000 0.0000 0.0000 0.02565(19) Uani 1 2 a d S . .
F1 F 0.7028(4) -0.25309(10) 0.1511(2) 0.0619(7) Uani 1 4 e d . . .
O1W O -0.202(3) 0.0035(6) 0.4625(8) 0.221(7) Uani 0.563(8) 4 e d P A 1
O2W O -0.506(4) -0.0505(8) 0.4265(9) 0.221(7) Uani 0.437(8) 4 e d P A 2
O1 O -0.2163(4) 0.00200(9) 0.10564(17) 0.0289(5) Uani 1 4 e d . . .
O2 O -0.3559(5) -0.01418(13) 0.2467(2) 0.0561(8) Uani 1 4 e d . . .
O3 O 0.1554(4) -0.07728(9) 0.07895(16) 0.0317(5) Uani 1 4 e d . . .
N1 N 0.0097(5) -0.17002(12) 0.3316(2) 0.0357(7) Uani 1 4 e d . . .
N2 N 0.2788(5) -0.24618(12) 0.3150(2) 0.0326(6) Uani 1 4 e d . . .
N3 N 0.5399(5) -0.32489(12) 0.3052(2) 0.0329(6) Uani 1 4 e d . . .
N4 N 0.7437(4) -0.43997(12) 0.3958(2) 0.0277(6) Uani 1 4 e d D . .
H4 H 0.643(4) -0.4663(13) 0.368(2) 0.038(10) Uiso 1 4 e d D . .
C1 C -0.2234(5) -0.02747(15) 0.1872(2) 0.0293(7) Uani 1 4 e d . . .
C2 C -0.0685(5) -0.08300(14) 0.2142(2) 0.0290(7) Uani 1 4 e d . . .
C3 C 0.1067(5) -0.10269(13) 0.1585(2) 0.0269(7) Uani 1 4 e d . . .
C4 C 0.2312(5) -0.15796(14) 0.1985(2) 0.0278(7) Uani 1 4 e d . . .
C5 C 0.4137(6) -0.18112(15) 0.1555(3) 0.0338(7) Uani 1 4 e d . . .
H5 H 0.4628 -0.1594 0.1024 0.041 Uiso 1 4 e calc R . .
C6 C 0.5176(5) -0.23413(15) 0.1903(3) 0.0345(8) Uani 1 4 e d . . .
C7 C 0.4442(5) -0.26994(14) 0.2697(2) 0.0302(7) Uani 1 4 e d . . .
C8 C 0.1791(5) -0.19215(14) 0.2814(2) 0.0305(7) Uani 1 4 e d . . .
C9 C -0.1021(6) -0.11752(15) 0.2975(2) 0.0348(8) Uani 1 4 e d . . .
H9 H -0.2125 -0.1033 0.3338 0.042 Uiso 1 4 e calc R . .
C10 C -0.0425(7) -0.20155(18) 0.4252(3) 0.0492(10) Uani 1 4 e d . . .
H10A H -0.2013 -0.1941 0.4301 0.059 Uiso 1 4 e calc R . .
H10B H -0.0217 -0.2461 0.4191 0.059 Uiso 1 4 e calc R . .
C11 C 0.1054(10) -0.1790(3) 0.5195(4) 0.0907(18) Uani 1 4 e d . . .
H11A H 0.2629 -0.1838 0.5131 0.136 Uiso 1 4 e calc R . .
H11B H 0.0761 -0.2027 0.5775 0.136 Uiso 1 4 e calc R . .
H11C H 0.0737 -0.1358 0.5296 0.136 Uiso 1 4 e calc R . .
C12 C 0.6307(7) -0.37106(16) 0.2414(3) 0.0437(9) Uani 1 4 e d . . .
H12A H 0.6937 -0.3501 0.1876 0.052 Uiso 1 4 e calc R . .
H12B H 0.5084 -0.3983 0.2089 0.052 Uiso 1 4 e calc R . .
C13 C 0.8164(6) -0.40928(16) 0.3081(3) 0.0411(8) Uani 1 4 e d . . .
H13A H 0.8701 -0.4408 0.2655 0.049 Uiso 1 4 e calc R . .
H13B H 0.9446 -0.3821 0.3338 0.049 Uiso 1 4 e calc R . .
C14 C 0.4505(6) -0.35619(17) 0.3882(3) 0.0488(10) Uani 1 4 e d . . .
H14A H 0.3251 -0.3834 0.3590 0.059 Uiso 1 4 e calc R . .
H14B H 0.3922 -0.3254 0.4307 0.059 Uiso 1 4 e calc R . .
C15 C 0.6372(6) -0.39388(16) 0.4535(3) 0.0411(9) Uani 1 4 e d . . .
H15A H 0.7545 -0.3656 0.4874 0.049 Uiso 1 4 e calc R . .
H15B H 0.5731 -0.4152 0.5066 0.049 Uiso 1 4 e calc R . .
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'
F F 0.0171 0.0103 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.00(10) 3 . ?
O1 Zn1 O3 87.27(8) 3 3 ?
O1 Zn1 O3 92.73(8) . 3 ?
O1 Zn1 O3 92.73(8) 3 . ?
O1 Zn1 O3 87.27(8) . . ?
O3 Zn1 O3 180.00(12) 3 . ?
O1 Zn1 N4 89.43(10) 3 2_655 ?
O1 Zn1 N4 90.57(10) . 2_655 ?
O3 Zn1 N4 92.26(9) 3 2_655 ?
O3 Zn1 N4 87.74(9) . 2_655 ?
O1 Zn1 N4 90.57(10) 3 4_455 ?
O1 Zn1 N4 89.43(10) . 4_455 ?
O3 Zn1 N4 87.74(9) 3 4_455 ?
O3 Zn1 N4 92.26(9) . 4_455 ?
N4 Zn1 N4 180.00(15) 2_655 4_455 ?
C1 O1 Zn1 133.7(2) . . ?
C3 O3 Zn1 127.79(19) . . ?
C9 N1 C8 119.0(3) . . ?
C9 N1 C10 119.7(3) . . ?
C8 N1 C10 121.3(3) . . ?
C7 N2 C8 119.9(3) . . ?
C7 N3 C14 118.2(3) . . ?
C7 N3 C12 124.4(3) . . ?
C14 N3 C12 109.9(3) . . ?
C15 N4 C13 109.0(2) . . ?
C15 N4 Zn1 112.10(19) . 2_645 ?
C13 N4 Zn1 118.4(2) . 2_645 ?
C15 N4 H4 110(2) . . ?
C13 N4 H4 104(2) . . ?
Zn1 N4 H4 103(2) 2_645 . ?
O2 C1 O1 123.4(3) . . ?
O2 C1 C2 117.5(3) . . ?
O1 C1 C2 119.2(3) . . ?
C9 C2 C3 118.3(3) . . ?
C9 C2 C1 116.5(3) . . ?
C3 C2 C1 125.2(3) . . ?
O3 C3 C2 126.3(3) . . ?
O3 C3 C4 118.6(3) . . ?
C2 C3 C4 115.1(3) . . ?
C8 C4 C5 115.3(3) . . ?
C8 C4 C3 123.1(3) . . ?
C5 C4 C3 121.7(3) . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 F1 118.6(3) . . ?
C5 C6 C7 121.8(3) . . ?
F1 C6 C7 119.5(3) . . ?
N2 C7 N3 118.2(3) . . ?
N2 C7 C6 117.8(3) . . ?
N3 C7 C6 123.9(3) . . ?
N2 C8 N1 117.0(3) . . ?
N2 C8 C4 124.5(3) . . ?
N1 C8 C4 118.5(3) . . ?
N1 C9 C2 126.0(3) . . ?
N1 C9 H9 117.0 . . ?
C2 C9 H9 117.0 . . ?
C11 C10 N1 111.8(4) . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
N1 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 C13 109.6(3) . . ?
N3 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
N3 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N4 C13 C12 114.4(3) . . ?
N4 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
N4 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
N3 C14 C15 110.2(3) . . ?
N3 C14 H14A 109.6 . . ?
C15 C14 H14A 109.6 . . ?
N3 C14 H14B 109.6 . . ?
C15 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C14 114.1(3) . . ?
N4 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
N4 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.059(2) 3 ?
Zn1 O1 2.059(2) . ?
Zn1 O3 2.084(2) 3 ?
Zn1 O3 2.084(2) . ?
Zn1 N4 2.262(3) 2_655 ?
Zn1 N4 2.262(3) 4_455 ?
F1 C6 1.359(4) . ?
O1 C1 1.255(4) . ?
O2 C1 1.242(4) . ?
O3 C3 1.262(3) . ?
N1 C9 1.344(4) . ?
N1 C8 1.385(4) . ?
N1 C10 1.489(4) . ?
N2 C7 1.339(4) . ?
N2 C8 1.341(4) . ?
N3 C7 1.355(4) . ?
N3 C14 1.463(4) . ?
N3 C12 1.465(4) . ?
N4 C15 1.460(4) . ?
N4 C13 1.462(4) . ?
N4 Zn1 2.262(3) 2_645 ?
N4 H4 0.86(3) . ?
C1 C2 1.509(4) . ?
C2 C9 1.370(4) . ?
C2 C3 1.441(4) . ?
C3 C4 1.446(4) . ?
C4 C8 1.398(4) . ?
C4 C5 1.402(4) . ?
C5 C6 1.336(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.470(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.522(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.511(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 Zn1 O1 C1 -172.9(3) 3 . . . ?
O3 Zn1 O1 C1 7.1(3) . . . . ?
N4 Zn1 O1 C1 -80.6(3) 2_655 . . . ?
N4 Zn1 O1 C1 99.4(3) 4_455 . . . ?
O1 Zn1 O3 C3 178.9(2) 3 . . . ?
O1 Zn1 O3 C3 -1.1(2) . . . . ?
N4 Zn1 O3 C3 89.6(2) 2_655 . . . ?
N4 Zn1 O3 C3 -90.4(2) 4_455 . . . ?
Zn1 O1 C1 O2 171.6(2) . . . . ?
Zn1 O1 C1 C2 -10.0(4) . . . . ?
O2 C1 C2 C9 5.8(5) . . . . ?
O1 C1 C2 C9 -172.7(3) . . . . ?
O2 C1 C2 C3 -175.4(3) . . . . ?
O1 C1 C2 C3 6.1(5) . . . . ?
Zn1 O3 C3 C2 -0.9(4) . . . . ?
Zn1 O3 C3 C4 177.4(2) . . . . ?
C9 C2 C3 O3 178.0(3) . . . . ?
C1 C2 C3 O3 -0.8(5) . . . . ?
C9 C2 C3 C4 -0.3(4) . . . . ?
C1 C2 C3 C4 -179.2(3) . . . . ?
O3 C3 C4 C8 -175.1(3) . . . . ?
C2 C3 C4 C8 3.3(4) . . . . ?
O3 C3 C4 C5 4.6(5) . . . . ?
C2 C3 C4 C5 -177.0(3) . . . . ?
C8 C4 C5 C6 3.4(5) . . . . ?
C3 C4 C5 C6 -176.4(3) . . . . ?
C4 C5 C6 F1 -176.0(3) . . . . ?
C4 C5 C6 C7 1.7(5) . . . . ?
C8 N2 C7 N3 -179.5(3) . . . . ?
C8 N2 C7 C6 3.7(5) . . . . ?
C14 N3 C7 N2 2.4(5) . . . . ?
C12 N3 C7 N2 148.9(3) . . . . ?
C14 N3 C7 C6 179.0(3) . . . . ?
C12 N3 C7 C6 -34.5(5) . . . . ?
C5 C6 C7 N2 -5.5(5) . . . . ?
F1 C6 C7 N2 172.2(3) . . . . ?
C5 C6 C7 N3 177.9(3) . . . . ?
F1 C6 C7 N3 -4.3(5) . . . . ?
C7 N2 C8 N1 -179.8(3) . . . . ?
C7 N2 C8 C4 1.7(5) . . . . ?
C9 N1 C8 N2 -177.0(3) . . . . ?
C10 N1 C8 N2 6.0(5) . . . . ?
C9 N1 C8 C4 1.6(5) . . . . ?
C10 N1 C8 C4 -175.4(3) . . . . ?
C5 C4 C8 N2 -5.3(5) . . . . ?
C3 C4 C8 N2 174.4(3) . . . . ?
C5 C4 C8 N1 176.3(3) . . . . ?
C3 C4 C8 N1 -4.0(5) . . . . ?
C8 N1 C9 C2 1.5(5) . . . . ?
C10 N1 C9 C2 178.5(3) . . . . ?
C3 C2 C9 N1 -2.1(5) . . . . ?
C1 C2 C9 N1 176.9(3) . . . . ?
C9 N1 C10 C11 -90.6(4) . . . . ?
C8 N1 C10 C11 86.5(4) . . . . ?
C7 N3 C12 C13 153.3(3) . . . . ?
C14 N3 C12 C13 -57.8(4) . . . . ?
C15 N4 C13 C12 -51.6(4) . . . . ?
Zn1 N4 C13 C12 178.8(2) 2_645 . . . ?
N3 C12 C13 N4 55.9(4) . . . . ?
C7 N3 C14 C15 -150.4(3) . . . . ?
C12 N3 C14 C15 58.6(4) . . . . ?
C13 N4 C15 C14 51.8(4) . . . . ?
Zn1 N4 C15 C14 -175.2(2) 2_645 . . . ?
N3 C14 C15 N4 -56.8(4) . . . . ?
