#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/10/2221076.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_2221076
loop_
_publ_author_name
'Qi, Wei'
'Gao, Jing'
'Liang, Di'
'An, Zhe'
_publ_section_title
Bis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato-κ²O³,O⁴]copper(II)
_journal_coeditor_code           HB2904
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m248
_journal_paper_doi               10.1107/S1600536809003584
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu (C17 H19 F N3 O3)2]'
_chemical_formula_moiety         'C34 H38 Cu F2 N6 O6'
_chemical_formula_sum            'C34 H38 Cu F2 N6 O6'
_chemical_formula_weight         728.24
_chemical_name_systematic
;
Bis[1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-
3-carboxylato-κ²O³,O⁴]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           SHELXL-97
_cell_angle_alpha                95.22(3)
_cell_angle_beta                 109.63(3)
_cell_angle_gamma                108.01(3)
_cell_formula_units_Z            1
_cell_length_a                   8.5548(17)
_cell_length_b                   10.253(2)
_cell_length_c                   10.467(2)
_cell_measurement_reflns_used    7808
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.13
_cell_volume                     802.7(4)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7880
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.13
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  0.871
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             379
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.367
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.137
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0334
_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)+(0.06P)²+0.1742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1030
_reflns_number_gt                3274
_reflns_number_total             3633
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2904.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2221076
_cod_database_fobs_code          2221076
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.5000 0.5000 0.02371(11) Uani d S 1 . .
F F1 0.82563(18) 0.16415(13) 0.12581(17) 0.0524(4) Uani d . 1 . .
O O1 0.59169(18) 0.69304(14) 0.50180(16) 0.0337(3) Uani d . 1 . .
O O2 0.7906(2) 0.89436(16) 0.5126(2) 0.0579(5) Uani d . 1 . .
O O3 0.63511(17) 0.45479(13) 0.39993(15) 0.0302(3) Uani d . 1 . .
N N1 1.09849(19) 0.72064(15) 0.39047(16) 0.0239(3) Uani d . 1 . .
N N2 1.1346(2) 0.33064(16) 0.10980(17) 0.0291(3) Uani d . 1 . .
N N3 1.3578(2) 0.24538(19) -0.00270(19) 0.0353(4) Uani d . 1 . .
C C1 0.7358(3) 0.76677(19) 0.4892(2) 0.0294(4) Uani d . 1 . .
C C2 0.8370(2) 0.69045(18) 0.44045(19) 0.0244(4) Uani d . 1 . .
C C3 0.7735(2) 0.54329(18) 0.39289(18) 0.0231(3) Uani d . 1 . .
C C4 0.8738(2) 0.49016(18) 0.32802(19) 0.0233(3) Uani d . 1 . .
C C5 0.8070(2) 0.34754(19) 0.2611(2) 0.0297(4) Uani d . 1 . .
H H5A 0.7014 0.2864 0.2617 0.036 Uiso calc R 1 . .
C C6 0.8976(3) 0.30001(19) 0.1959(2) 0.0315(4) Uani d . 1 . .
C C7 1.0598(2) 0.38636(19) 0.1906(2) 0.0267(4) Uani d . 1 . .
C C8 1.1264(2) 0.52630(19) 0.2581(2) 0.0258(4) Uani d . 1 . .
H H8A 1.2336 0.5861 0.2587 0.031 Uiso calc R 1 . .
C C9 1.0346(2) 0.57967(18) 0.32596(18) 0.0227(3) Uani d . 1 . .
C C10 0.9982(2) 0.77176(18) 0.43938(19) 0.0254(4) Uani d . 1 . .
H H10A 1.0400 0.8680 0.4748 0.031 Uiso calc R 1 . .
C C11 1.2746(2) 0.81963(19) 0.4025(2) 0.0307(4) Uani d . 1 . .
H H11A 1.3593 0.7721 0.4229 0.037 Uiso calc R 1 . .
H H11B 1.3171 0.8985 0.4797 0.037 Uiso calc R 1 . .
C C12 1.2671(3) 0.8743(2) 0.2716(3) 0.0470(6) Uani d . 1 . .
H H12A 1.2253 0.7967 0.1948 0.071 Uiso calc R 1 . .
H H12B 1.3839 0.9358 0.2840 0.071 Uiso calc R 1 . .
H H12C 1.1873 0.9249 0.2530 0.071 Uiso calc R 1 . .
C C13 1.2615(3) 0.4313(2) 0.0678(2) 0.0326(4) Uani d . 1 . .
H H13A 1.3746 0.4760 0.1459 0.039 Uiso calc R 1 . .
H H13B 1.2165 0.5036 0.0366 0.039 Uiso calc R 1 . .
C C14 1.2866(3) 0.3524(2) -0.0493(2) 0.0333(4) Uani d . 1 . .
H H14A 1.1732 0.3084 -0.1272 0.040 Uiso calc R 1 . .
H H14B 1.3677 0.4179 -0.0803 0.040 Uiso calc R 1 . .
C C15 1.2292(3) 0.1448(2) 0.0361(2) 0.0352(4) Uani d . 1 . .
H H15A 1.2732 0.0716 0.0657 0.042 Uiso calc R 1 . .
H H15B 1.1178 0.1013 -0.0439 0.042 Uiso calc R 1 . .
C C16 1.1970(3) 0.2168(2) 0.1528(2) 0.0332(4) Uani d . 1 . .
H H16A 1.1085 0.1490 0.1757 0.040 Uiso calc R 1 . .
H H16B 1.3065 0.2551 0.2349 0.040 Uiso calc R 1 . .
C C17 1.3936(4) 0.1748(3) -0.1120(3) 0.0563(7) Uani d . 1 . .
H H17A 1.4481 0.1096 -0.0768 0.084 Uiso calc R 1 . .
H H17B 1.4724 0.2435 -0.1407 0.084 Uiso calc R 1 . .
H H17C 1.2838 0.1252 -0.1900 0.084 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 2_666 . 180.0 ?
O1 Cu1 O3 2_666 . 87.35(6) ?
O1 Cu1 O3 . . 92.65(6) ?
O1 Cu1 O3 2_666 2_666 92.65(6) ?
O1 Cu1 O3 . 2_666 87.35(6) ?
O3 Cu1 O3 . 2_666 180.0 ?
C1 O1 Cu1 . . 130.33(12) ?
C3 O3 Cu1 . . 124.62(12) ?
C10 N1 C9 . . 119.95(15) ?
C10 N1 C11 . . 118.31(15) ?
C9 N1 C11 . . 121.70(14) ?
C7 N2 C13 . . 116.83(15) ?
C7 N2 C16 . . 117.25(15) ?
C13 N2 C16 . . 111.04(15) ?
C15 N3 C14 . . 108.25(16) ?
C15 N3 C17 . . 110.58(18) ?
C14 N3 C17 . . 110.99(18) ?
O2 C1 O1 . . 122.66(17) ?
O2 C1 C2 . . 119.20(17) ?
O1 C1 C2 . . 118.13(16) ?
C10 C2 C3 . . 119.32(16) ?
C10 C2 C1 . . 116.81(15) ?
C3 C2 C1 . . 123.84(16) ?
O3 C3 C2 . . 125.72(16) ?
O3 C3 C4 . . 118.07(15) ?
C2 C3 C4 . . 116.19(15) ?
C9 C4 C5 . . 118.77(16) ?
C9 C4 C3 . . 121.23(16) ?
C5 C4 C3 . . 119.96(16) ?
C6 C5 C4 . . 119.63(17) ?
C6 C5 H5A . . 120.2 ?
C4 C5 H5A . . 120.2 ?
C5 C6 F1 . . 118.45(17) ?
C5 C6 C7 . . 123.62(17) ?
F1 C6 C7 . . 117.85(16) ?
C8 C7 N2 . . 123.85(16) ?
C8 C7 C6 . . 116.62(16) ?
N2 C7 C6 . . 119.30(16) ?
C7 C8 C9 . . 121.24(16) ?
C7 C8 H8A . . 119.4 ?
C9 C8 H8A . . 119.4 ?
N1 C9 C4 . . 118.52(15) ?
N1 C9 C8 . . 121.36(15) ?
C4 C9 C8 . . 120.11(16) ?
N1 C10 C2 . . 124.01(16) ?
N1 C10 H10A . . 118.0 ?
C2 C10 H10A . . 118.0 ?
N1 C11 C12 . . 112.76(17) ?
N1 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
N1 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
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 . . 108.39(16) ?
N2 C13 H13A . . 110.0 ?
C14 C13 H13A . . 110.0 ?
N2 C13 H13B . . 110.0 ?
C14 C13 H13B . . 110.0 ?
H13A C13 H13B . . 108.4 ?
N3 C14 C13 . . 110.51(17) ?
N3 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
N3 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
N3 C15 C16 . . 110.62(17) ?
N3 C15 H15A . . 109.5 ?
C16 C15 H15A . . 109.5 ?
N3 C15 H15B . . 109.5 ?
C16 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
N2 C16 C15 . . 109.86(16) ?
N2 C16 H16A . . 109.7 ?
C15 C16 H16A . . 109.7 ?
N2 C16 H16B . . 109.7 ?
C15 C16 H16B . . 109.7 ?
H16A C16 H16B . . 108.2 ?
N3 C17 H17A . . 109.5 ?
N3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
N3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
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
Cu1 O1 2_666 1.8858(15) ?
Cu1 O1 . 1.8858(15) y
Cu1 O3 . 1.9247(13) y
Cu1 O3 2_666 1.9247(13) ?
F1 C6 . 1.356(2) ?
O1 C1 . 1.288(2) ?
O2 C1 . 1.215(2) ?
O3 C3 . 1.279(2) ?
N1 C10 . 1.341(2) ?
N1 C9 . 1.389(2) ?
N1 C11 . 1.490(2) ?
N2 C7 . 1.397(2) ?
N2 C13 . 1.465(2) ?
N2 C16 . 1.473(2) ?
N3 C15 . 1.454(3) ?
N3 C14 . 1.458(3) ?
N3 C17 . 1.465(3) ?
C1 C2 . 1.505(2) ?
C2 C10 . 1.378(2) ?
C2 C3 . 1.412(2) ?
C3 C4 . 1.451(2) ?
C4 C9 . 1.406(2) ?
C4 C5 . 1.408(3) ?
C5 C6 . 1.354(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.419(3) ?
C7 C8 . 1.387(3) ?
C8 C9 . 1.411(2) ?
C8 H8A . 0.9300 ?
C10 H10A . 0.9300 ?
C11 C12 . 1.517(3) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 C14 . 1.517(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 C16 . 1.516(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
O3 Cu1 O1 C1 . . . . -22.51(19) ?
O3 Cu1 O1 C1 2_666 . . . 157.49(19) ?
O1 Cu1 O3 C3 2_666 . . . -160.14(16) ?
O1 Cu1 O3 C3 . . . . 19.86(16) ?
Cu1 O1 C1 O2 . . . . -168.97(18) ?
Cu1 O1 C1 C2 . . . . 12.5(3) ?
O2 C1 C2 C10 . . . . 6.8(3) ?
O1 C1 C2 C10 . . . . -174.60(18) ?
O2 C1 C2 C3 . . . . -171.3(2) ?
O1 C1 C2 C3 . . . . 7.3(3) ?
Cu1 O3 C3 C2 . . . . -8.9(3) ?
Cu1 O3 C3 C4 . . . . 172.47(12) ?
C10 C2 C3 O3 . . . . 173.24(17) ?
C1 C2 C3 O3 . . . . -8.7(3) ?
C10 C2 C3 C4 . . . . -8.1(3) ?
C1 C2 C3 C4 . . . . 169.88(17) ?
O3 C3 C4 C9 . . . . -175.10(16) ?
C2 C3 C4 C9 . . . . 6.2(3) ?
O3 C3 C4 C5 . . . . 7.3(3) ?
C2 C3 C4 C5 . . . . -171.48(17) ?
C9 C4 C5 C6 . . . . -0.4(3) ?
C3 C4 C5 C6 . . . . 177.27(18) ?
C4 C5 C6 F1 . . . . -176.44(19) ?
C4 C5 C6 C7 . . . . 0.2(3) ?
C13 N2 C7 C8 . . . . -15.2(3) ?
C16 N2 C7 C8 . . . . 120.3(2) ?
C13 N2 C7 C6 . . . . 159.03(19) ?
C16 N2 C7 C6 . . . . -65.5(2) ?
C5 C6 C7 C8 . . . . 0.6(3) ?
F1 C6 C7 C8 . . . . 177.28(18) ?
C5 C6 C7 N2 . . . . -174.06(19) ?
F1 C6 C7 N2 . . . . 2.6(3) ?
N2 C7 C8 C9 . . . . 173.18(17) ?
C6 C7 C8 C9 . . . . -1.2(3) ?
C10 N1 C9 C4 . . . . -7.3(3) ?
C11 N1 C9 C4 . . . . 175.07(17) ?
C10 N1 C9 C8 . . . . 171.97(17) ?
C11 N1 C9 C8 . . . . -5.6(3) ?
C5 C4 C9 N1 . . . . 179.12(17) ?
C3 C4 C9 N1 . . . . 1.4(3) ?
C5 C4 C9 C8 . . . . -0.2(3) ?
C3 C4 C9 C8 . . . . -177.85(16) ?
C7 C8 C9 N1 . . . . -178.24(17) ?
C7 C8 C9 C4 . . . . 1.0(3) ?
C9 N1 C10 C2 . . . . 5.5(3) ?
C11 N1 C10 C2 . . . . -176.84(18) ?
C3 C2 C10 N1 . . . . 2.7(3) ?
C1 C2 C10 N1 . . . . -175.49(17) ?
C10 N1 C11 C12 . . . . -95.8(2) ?
C9 N1 C11 C12 . . . . 81.9(2) ?
C7 N2 C13 C14 . . . . -164.32(17) ?
C16 N2 C13 C14 . . . . 57.6(2) ?
C15 N3 C14 C13 . . . . 62.2(2) ?
C17 N3 C14 C13 . . . . -176.26(18) ?
N2 C13 C14 N3 . . . . -60.8(2) ?
C14 N3 C15 C16 . . . . -60.3(2) ?
C17 N3 C15 C16 . . . . 178.0(2) ?
C7 N2 C16 C15 . . . . 165.57(17) ?
C13 N2 C16 C15 . . . . -56.5(2) ?
N3 C15 C16 N2 . . . . 57.7(2) ?
