#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/65/2216506.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_2216506
loop_
_publ_author_name
'Wen Xu'
'Zhe An'
_publ_section_title
;Poly[[bis[μ-1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylato]nickel(II)]
 dihydrate]
;
_journal_coeditor_code           HB2657
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m3157
_journal_page_last               m3157
_journal_paper_doi               10.1107/S1600536807060813
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Ni (C16 H17 F N3 O3)2], 2H2 O'
_chemical_formula_moiety         'C32 H34 F2 N6 Ni O6, 2(H2 O)'
_chemical_formula_sum            'C32 H38 F2 N6 Ni O8'
_chemical_formula_weight         727.36
_chemical_name_systematic
;
Poly[[bis[μ-1-ethyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-
3-carboxylato]nickel(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                 100.7630(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.8389(2)
_cell_length_b                   21.5704(8)
_cell_length_c                   13.2408(4)
_cell_measurement_reflns_used    8072
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.49
_cell_measurement_theta_min      1.83
_cell_volume                     1638.31(10)
_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  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD'
_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  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8473
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  0.890
_exptl_absorpt_correction_T_min  0.816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.356
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0346
_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)+(0.0692P)²+1.1691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                2766
_reflns_number_total             3037
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2657.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2216506
_cod_database_fobs_code          2216506
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 -0.212(3) 0.5083(3) 0.9619(4) 0.269(7) Uani d P 0.771(7) A 1
O O2W -0.530(7) 0.4676(10) 0.9199(13) 0.269(7) Uani d P 0.229(7) A 2
Ni Ni1 0.0000 0.5000 0.5000 0.02183(14) Uani d S 1 . .
F F1 0.6987(2) 0.25278(6) 0.66313(11) 0.0456(4) Uani d . 1 . .
O O1 -0.2244(3) 0.50862(6) 0.60039(12) 0.0278(3) Uani d . 1 . .
O O2 -0.3489(4) 0.50317(7) 0.74766(15) 0.0507(5) Uani d . 1 . .
O O3 0.1702(2) 0.43116(6) 0.59199(10) 0.0270(3) Uani d . 1 . .
N N1 -0.0082(3) 0.34446(8) 0.84271(12) 0.0288(4) Uani d . 1 . .
N N2 0.5781(3) 0.18573(8) 0.82650(13) 0.0282(4) Uani d . 1 . .
N N3 0.7581(3) 0.06548(7) 0.90923(13) 0.0260(4) Uani d D 1 . .
H H3N 0.633(3) 0.0444(11) 0.893(2) 0.046(7) Uiso d D 1 . .
C C1 -0.2232(4) 0.48474(9) 0.68784(16) 0.0276(4) Uani d . 1 . .
C C2 -0.0695(3) 0.42936(8) 0.72119(14) 0.0259(4) Uani d . 1 . .
C C3 0.1112(3) 0.40744(8) 0.67023(14) 0.0236(4) Uani d . 1 . .
C C4 0.2286(3) 0.35113(8) 0.71319(14) 0.0244(4) Uani d . 1 . .
C C5 0.4086(3) 0.32589(9) 0.66939(15) 0.0279(4) Uani d . 1 . .
H H5 0.4551 0.3462 0.6146 0.034 Uiso calc R 1 . .
C C6 0.5158(3) 0.27262(9) 0.70514(16) 0.0281(4) Uani d . 1 . .
C C7 0.4534(3) 0.23790(9) 0.78697(15) 0.0260(4) Uani d . 1 . .
C C8 0.2748(3) 0.26310(9) 0.83045(15) 0.0285(4) Uani d . 1 . .
H H8 0.2258 0.2419 0.8838 0.034 Uiso calc R 1 . .
C C9 0.1661(3) 0.31940(9) 0.79669(15) 0.0257(4) Uani d . 1 . .
C C10 -0.1149(3) 0.39704(9) 0.80463(15) 0.0285(4) Uani d . 1 . .
H H10 -0.2294 0.4129 0.8377 0.034 Uiso calc R 1 . .
C C11 -0.0729(4) 0.31627(11) 0.93573(17) 0.0370(5) Uani d . 1 . .
H H11A -0.0875 0.2718 0.9260 0.044 Uiso calc R 1 . .
H H11B -0.2239 0.3321 0.9438 0.044 Uiso calc R 1 . .
C C12 0.1007(6) 0.32911(15) 1.0321(2) 0.0613(8) Uani d . 1 . .
H H12A 0.2522 0.3153 1.0236 0.092 Uiso calc R 1 . .
H H12B 0.0557 0.3074 1.0886 0.092 Uiso calc R 1 . .
H H12C 0.1054 0.3728 1.0459 0.092 Uiso calc R 1 . .
C C13 0.5224(5) 0.16096(11) 0.92160(18) 0.0445(6) Uani d . 1 . .
H H13A 0.3755 0.1387 0.9065 0.053 Uiso calc R 1 . .
H H13B 0.5053 0.1948 0.9678 0.053 Uiso calc R 1 . .
C C14 0.7127(5) 0.11770(11) 0.97288(17) 0.0428(6) Uani d . 1 . .
H H14A 0.8555 0.1413 0.9925 0.051 Uiso calc R 1 . .
H H14B 0.6702 0.1017 1.0353 0.051 Uiso calc R 1 . .
C C15 0.6156(4) 0.13449(10) 0.75747(16) 0.0351(5) Uani d . 1 . .
H H15A 0.6624 0.1512 0.6964 0.042 Uiso calc R 1 . .
H H15B 0.4710 0.1119 0.7362 0.042 Uiso calc R 1 . .
C C16 0.8036(4) 0.09047(10) 0.81179(16) 0.0353(5) Uani d . 1 . .
H H16A 0.8185 0.0562 0.7661 0.042 Uiso calc R 1 . .
H H16B 0.9515 0.1123 0.8250 0.042 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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
O1 Ni1 O1 3_566 . 180.0
O1 Ni1 O3 3_566 . 91.26(5)
O1 Ni1 O3 . . 88.74(5)
O1 Ni1 O3 3_566 3_566 88.74(5)
O1 Ni1 O3 . 3_566 91.26(5)
O3 Ni1 O3 . 3_566 180.0
O1 Ni1 N3 3_566 4_465 90.60(6)
O1 Ni1 N3 . 4_465 89.40(6)
O3 Ni1 N3 . 4_465 92.88(6)
O3 Ni1 N3 3_566 4_465 87.12(6)
O1 Ni1 N3 3_566 2_656 89.40(6)
O1 Ni1 N3 . 2_656 90.60(6)
O3 Ni1 N3 . 2_656 87.12(6)
O3 Ni1 N3 3_566 2_656 92.88(6)
N3 Ni1 N3 4_465 2_656 180.0
C1 O1 Ni1 . . 131.60(13)
C3 O3 Ni1 . . 127.19(12)
C10 N1 C9 . . 119.29(16)
C10 N1 C11 . . 118.96(16)
C9 N1 C11 . . 121.70(16)
C7 N2 C13 . . 115.85(16)
C7 N2 C15 . . 120.08(16)
C13 N2 C15 . . 110.05(17)
C14 N3 C16 . . 107.83(16)
C14 N3 Ni1 . 2_646 110.40(12)
C16 N3 Ni1 . 2_646 121.00(13)
C14 N3 H3N . . 108.2(18)
C16 N3 H3N . . 105.5(18)
Ni1 N3 H3N 2_646 . 103.1(18)
O2 C1 O1 . . 123.41(18)
O2 C1 C2 . . 117.17(18)
O1 C1 C2 . . 119.38(18)
C10 C2 C3 . . 118.71(17)
C10 C2 C1 . . 116.33(17)
C3 C2 C1 . . 124.92(17)
O3 C3 C2 . . 126.23(17)
O3 C3 C4 . . 118.58(17)
C2 C3 C4 . . 115.15(16)
C5 C4 C9 . . 117.48(17)
C5 C4 C3 . . 119.79(17)
C9 C4 C3 . . 122.71(17)
C6 C5 C4 . . 121.30(18)
C6 C5 H5 . . 119.4
C4 C5 H5 . . 119.4
C5 C6 F1 . . 118.13(17)
C5 C6 C7 . . 123.23(19)
F1 C6 C7 . . 118.58(17)
N2 C7 C8 . . 122.76(18)
N2 C7 C6 . . 121.60(18)
C8 C7 C6 . . 115.36(18)
C7 C8 C9 . . 122.36(18)
C7 C8 H8 . . 118.8
C9 C8 H8 . . 118.8
N1 C9 C8 . . 121.44(17)
N1 C9 C4 . . 118.35(17)
C8 C9 C4 . . 120.20(18)
N1 C10 C2 . . 125.71(18)
N1 C10 H10 . . 117.1
C2 C10 H10 . . 117.1
N1 C11 C12 . . 113.2(2)
N1 C11 H11A . . 108.9
C12 C11 H11A . . 108.9
N1 C11 H11B . . 108.9
C12 C11 H11B . . 108.9
H11A C11 H11B . . 107.8
C11 C12 H12A . . 109.5
C11 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C11 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
N2 C13 C14 . . 110.48(18)
N2 C13 H13A . . 109.6
C14 C13 H13A . . 109.6
N2 C13 H13B . . 109.6
C14 C13 H13B . . 109.6
H13A C13 H13B . . 108.1
N3 C14 C13 . . 114.48(19)
N3 C14 H14A . . 108.6
C13 C14 H14A . . 108.6
N3 C14 H14B . . 108.6
C13 C14 H14B . . 108.6
H14A C14 H14B . . 107.6
N2 C15 C16 . . 110.53(16)
N2 C15 H15A . . 109.5
C16 C15 H15A . . 109.5
N2 C15 H15B . . 109.5
C16 C15 H15B . . 109.5
H15A C15 H15B . . 108.1
N3 C16 C15 . . 114.23(17)
N3 C16 H16A . . 108.7
C15 C16 H16A . . 108.7
N3 C16 H16B . . 108.7
C15 C16 H16B . . 108.7
H16A C16 H16B . . 107.6
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
Ni1 O1 3_566 2.0415(15) ?
Ni1 O1 . 2.0415(15) y
Ni1 O3 . 2.0552(13) y
Ni1 O3 3_566 2.0552(13) ?
Ni1 N3 4_465 2.1908(16) ?
Ni1 N3 2_656 2.1908(16) y
F1 C6 . 1.362(2) ?
O1 C1 . 1.266(3) ?
O2 C1 . 1.241(3) ?
O3 C3 . 1.260(2) ?
N1 C10 . 1.346(2) ?
N1 C9 . 1.389(2) ?
N1 C11 . 1.484(2) ?
N2 C7 . 1.389(2) ?
N2 C13 . 1.460(3) ?
N2 C15 . 1.476(3) ?
N3 C14 . 1.461(3) ?
N3 C16 . 1.468(3) ?
N3 Ni1 2_646 2.1908(16) ?
N3 H3N . 0.852(10) ?
C1 C2 . 1.510(3) ?
C2 C10 . 1.373(3) ?
C2 C3 . 1.435(3) ?
C3 C4 . 1.457(3) ?
C4 C5 . 1.401(3) ?
C4 C9 . 1.405(3) ?
C5 C6 . 1.351(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.419(3) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.404(3) ?
C8 H8 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 C12 . 1.500(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.512(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.526(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 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
N3 H3N O2 2_546 0.852(10) 2.425(17) 3.159(2) 145(2)
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
O3 Ni1 O1 C1 . 7.83(18)
N3 Ni1 O1 C1 4_465 100.72(18)
N3 Ni1 O1 C1 2_656 -79.28(18)
O1 Ni1 O3 C3 3_566 -174.28(15)
O1 Ni1 O3 C3 . 5.72(15)
N3 Ni1 O3 C3 4_465 -83.62(15)
N3 Ni1 O3 C3 2_656 96.38(15)
Ni1 O1 C1 O2 . 166.39(17)
Ni1 O1 C1 C2 . -16.1(3)
O2 C1 C2 C10 . 12.3(3)
O1 C1 C2 C10 . -165.38(19)
O2 C1 C2 C3 . -170.1(2)
O1 C1 C2 C3 . 12.2(3)
Ni1 O3 C3 C2 . -9.7(3)
Ni1 O3 C3 C4 . 168.14(12)
C10 C2 C3 O3 . 178.57(18)
C1 C2 C3 O3 . 1.0(3)
C10 C2 C3 C4 . 0.7(3)
C1 C2 C3 C4 . -176.88(17)
O3 C3 C4 C5 . 2.2(3)
C2 C3 C4 C5 . -179.76(17)
O3 C3 C4 C9 . -176.37(17)
C2 C3 C4 C9 . 1.7(3)
C9 C4 C5 C6 . 0.9(3)
C3 C4 C5 C6 . -177.74(19)
C4 C5 C6 F1 . -176.03(18)
C4 C5 C6 C7 . 1.2(3)
C13 N2 C7 C8 . -4.2(3)
C15 N2 C7 C8 . 131.9(2)
C13 N2 C7 C6 . 169.5(2)
C15 N2 C7 C6 . -54.4(3)
C5 C6 C7 N2 . -175.37(18)
F1 C6 C7 N2 . 1.9(3)
C5 C6 C7 C8 . -1.2(3)
F1 C6 C7 C8 . 176.00(17)
N2 C7 C8 C9 . 173.20(18)
C6 C7 C8 C9 . -0.8(3)
C10 N1 C9 C8 . -176.91(19)
C11 N1 C9 C8 . 5.8(3)
C10 N1 C9 C4 . 1.7(3)
C11 N1 C9 C4 . -175.62(18)
C7 C8 C9 N1 . -178.50(19)
C7 C8 C9 C4 . 2.9(3)
C5 C4 C9 N1 . 178.51(17)
C3 C4 C9 N1 . -2.9(3)
C5 C4 C9 C8 . -2.9(3)
C3 C4 C9 C8 . 175.70(18)
C9 N1 C10 C2 . 0.8(3)
C11 N1 C10 C2 . 178.1(2)
C3 C2 C10 N1 . -2.0(3)
C1 C2 C10 N1 . 175.80(19)
C10 N1 C11 C12 . -101.8(2)
C9 N1 C11 C12 . 75.5(3)
C7 N2 C13 C14 . -163.1(2)
C15 N2 C13 C14 . 56.5(3)
C16 N3 C14 C13 . 53.9(3)
Ni1 N3 C14 C13 2_646 -171.88(17)
N2 C13 C14 N3 . -57.8(3)
C7 N2 C15 C16 . 166.05(18)
C13 N2 C15 C16 . -55.5(2)
C14 N3 C16 C15 . -52.7(2)
Ni1 N3 C16 C15 2_646 178.92(14)
N2 C15 C16 N3 . 55.4(2)
