#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/26/2222673.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_2222673
loop_
_publ_author_name
'Li, Tao'
'Tang, Li-Rong'
'Zeng, Qiao-Ling'
'Chen, Wei-Jin'
'Huang, Biao'
_publ_section_title
;1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic
 acid
;
_journal_coeditor_code           FB2160
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2053
_journal_paper_doi               10.1107/S1600536809029729
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H17 F N4 O4'
_chemical_formula_moiety         'C17 H17 F N4 O4'
_chemical_formula_sum            'C17 H17 F N4 O4'
_chemical_formula_weight         360.35
_chemical_name_systematic
;
1-Cyclopropyl-6-fluoro-7-(4-nitrosopiperazin-1-yl)-4-oxo-
1,4-dihydroquinoline-3-carboxylic acid
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                102.99(2)
_cell_angle_beta                 96.089(14)
_cell_angle_gamma                97.392(16)
_cell_formula_units_Z            2
_cell_length_a                   8.378(3)
_cell_length_b                   9.625(4)
_cell_length_c                   10.328(4)
_cell_measurement_reflns_used    771
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      27.4256
_cell_measurement_theta_min      2.0435
_cell_volume                     796.9(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2007)'
_computing_data_collection       'CrystalClear (Rigaku, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku, 2007)'
_computing_molecular_graphics
;
SHELXL97 (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Mercury CCD/AFC'
_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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6267
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.349
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    67
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0666
_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)+(0.1165P)²+0.047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2074
_reflns_number_gt                2568
_reflns_number_total             3631
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            fb2160.cif
_cod_data_source_block           I
_cod_original_cell_volume        797.0(6)
_cod_database_code               2222673
_cod_database_fobs_code          2222673
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
N N1 0.14474(19) 0.38921(17) 0.16119(15) 0.0330(4) Uani d . 1 . .
O O2 -0.1340(2) 0.09746(18) -0.25939(15) 0.0561(5) Uani d . 1 . .
H H18 -0.0827 0.1674 -0.2814 0.084 Uiso calc R 1 . .
O O3 0.0676(2) 0.32428(17) -0.25086(13) 0.0472(4) Uani d . 1 . .
C C8 0.2117(2) 0.4611(2) -0.03990(18) 0.0331(4) Uani d . 1 . .
F F1 0.51960(16) 0.74426(14) -0.07933(12) 0.0505(4) Uani d . 1 . .
C C13 0.2335(2) 0.48548(19) 0.10118(18) 0.0318(4) Uani d . 1 . .
C C11 0.4372(2) 0.6987(2) 0.1245(2) 0.0342(4) Uani d . 1 . .
C C5 0.0120(2) 0.2477(2) -0.05450(19) 0.0356(5) Uani d . 1 . .
O O1 -0.1742(2) 0.03235(18) -0.07173(17) 0.0580(5) Uani d . 1 . .
C C12 0.3415(2) 0.6063(2) 0.18211(19) 0.0344(4) Uani d . 1 . .
H H12A 0.3488 0.6247 0.2770 0.041 Uiso calc R 1 . .
C C9 0.3081(3) 0.5551(2) -0.0978(2) 0.0372(5) Uani d . 1 . .
H H9A 0.2962 0.5415 -0.1925 0.045 Uiso calc R 1 . .
N N2 0.5528(2) 0.81427(18) 0.20147(16) 0.0380(4) Uani d . 1 . .
C C7 0.0944(2) 0.3414(2) -0.1242(2) 0.0361(5) Uani d . 1 . .
C C10 0.4184(3) 0.6654(2) -0.0179(2) 0.0361(5) Uani d . 1 . .
C C4 0.0408(2) 0.2758(2) 0.0830(2) 0.0359(5) Uani d . 1 . .
H H4A -0.0163 0.2111 0.1257 0.043 Uiso calc R 1 . .
C C6 -0.1066(3) 0.1168(2) -0.1269(2) 0.0428(5) Uani d . 1 . .
N N3 0.7368(3) 1.0685(2) 0.37104(18) 0.0492(5) Uani d . 1 . .
C C3 0.1612(3) 0.4155(2) 0.30774(19) 0.0373(5) Uani d . 1 . .
H H3A 0.1132 0.4997 0.3544 0.045 Uiso calc R 1 . .
C C14 0.5794(3) 0.8301(2) 0.3473(2) 0.0473(6) Uani d . 1 . .
H H14A 0.5869 0.7346 0.3663 0.057 Uiso calc R 1 . .
H H14B 0.4859 0.8666 0.3870 0.057 Uiso calc R 1 . .
C C2 0.3112(3) 0.3878(3) 0.3816(2) 0.0512(6) Uani d . 1 . .
H H2A 0.3549 0.4545 0.4696 0.061 Uiso calc R 1 . .
H H2B 0.3943 0.3493 0.3283 0.061 Uiso calc R 1 . .
C C15 0.7354(3) 0.9344(2) 0.4114(2) 0.0487(6) Uani d . 1 . .
H H15A 0.7434 0.9535 0.5103 0.058 Uiso calc R 1 . .
H H15B 0.8306 0.8901 0.3840 0.058 Uiso calc R 1 . .
C C16 0.5548(3) 0.9558(3) 0.1687(2) 0.0570(7) Uani d . 1 . .
H H16A 0.4633 1.0008 0.2039 0.068 Uiso calc R 1 . .
H H16B 0.5390 0.9417 0.0700 0.068 Uiso calc R 1 . .
C C17 0.7110(3) 1.0550(3) 0.2268(2) 0.0574(7) Uani d . 1 . .
H H17A 0.8022 1.0156 0.1856 0.069 Uiso calc R 1 . .
H H17B 0.7058 1.1509 0.2082 0.069 Uiso calc R 1 . .
C C1 0.1525(3) 0.2910(3) 0.3709(2) 0.0551(7) Uani d . 1 . .
H H1A 0.1379 0.1929 0.3111 0.066 Uiso calc R 1 . .
H H1B 0.0986 0.2981 0.4524 0.066 Uiso calc R 1 . .
N N4 0.7544(3) 1.1903(2) 0.4635(2) 0.0654(7) Uani d . 1 . .
O O4 0.7463(3) 1.3001(2) 0.4211(2) 0.0895(7) Uani d . 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'
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
C4 N1 C13 . . 119.38(16) ?
C4 N1 C3 . . 120.52(15) ?
C13 N1 C3 . . 120.07(15) ?
C6 O2 H18 . . 109.5 ?
C9 C8 C13 . . 118.03(17) ?
C9 C8 C7 . . 120.60(17) ?
C13 C8 C7 . . 121.36(18) ?
N1 C13 C8 . . 119.20(16) ?
N1 C13 C12 . . 120.02(17) ?
C8 C13 C12 . . 120.77(17) ?
C12 C11 N2 . . 122.48(18) ?
C12 C11 C10 . . 116.46(17) ?
N2 C11 C10 . . 120.98(17) ?
C4 C5 C7 . . 120.37(17) ?
C4 C5 C6 . . 117.68(18) ?
C7 C5 C6 . . 121.95(18) ?
C11 C12 C13 . . 120.90(18) ?
C11 C12 H12A . . 119.6 ?
C13 C12 H12A . . 119.6 ?
C10 C9 C8 . . 119.97(18) ?
C10 C9 H9A . . 120.0 ?
C8 C9 H9A . . 120.0 ?
C11 N2 C14 . . 117.59(15) ?
C11 N2 C16 . . 117.81(17) ?
C14 N2 C16 . . 111.17(17) ?
O3 C7 C5 . . 123.16(18) ?
O3 C7 C8 . . 121.43(18) ?
C5 C7 C8 . . 115.41(17) ?
C9 C10 F1 . . 117.51(17) ?
C9 C10 C11 . . 123.63(18) ?
F1 C10 C11 . . 118.81(17) ?
N1 C4 C5 . . 124.20(18) ?
N1 C4 H4A . . 117.9 ?
C5 C4 H4A . . 117.9 ?
O1 C6 O2 . . 121.06(19) ?
O1 C6 C5 . . 123.8(2) ?
O2 C6 C5 . . 115.15(19) ?
N4 N3 C15 . . 119.31(19) ?
N4 N3 C17 . . 125.3(2) ?
C15 N3 C17 . . 115.35(18) ?
N1 C3 C1 . . 119.44(18) ?
N1 C3 C2 . . 119.07(18) ?
C1 C3 C2 . . 60.70(16) ?
N1 C3 H3A . . 115.5 ?
C1 C3 H3A . . 115.5 ?
C2 C3 H3A . . 115.5 ?
N2 C14 C15 . . 110.91(17) ?
N2 C14 H14A . . 109.5 ?
C15 C14 H14A . . 109.5 ?
N2 C14 H14B . . 109.5 ?
C15 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.0 ?
C3 C2 C1 . . 59.64(15) ?
C3 C2 H2A . . 117.8 ?
C1 C2 H2A . . 117.8 ?
C3 C2 H2B . . 117.8 ?
C1 C2 H2B . . 117.8 ?
H2A C2 H2B . . 114.9 ?
N3 C15 C14 . . 110.6(2) ?
N3 C15 H15A . . 109.5 ?
C14 C15 H15A . . 109.5 ?
N3 C15 H15B . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
N2 C16 C17 . . 111.9(2) ?
N2 C16 H16A . . 109.2 ?
C17 C16 H16A . . 109.2 ?
N2 C16 H16B . . 109.2 ?
C17 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
N3 C17 C16 . . 108.62(19) ?
N3 C17 H17A . . 110.0 ?
C16 C17 H17A . . 110.0 ?
N3 C17 H17B . . 110.0 ?
C16 C17 H17B . . 110.0 ?
H17A C17 H17B . . 108.3 ?
C3 C1 C2 . . 59.66(15) ?
C3 C1 H1A . . 117.8 ?
C2 C1 H1A . . 117.8 ?
C3 C1 H1B . . 117.8 ?
C2 C1 H1B . . 117.8 ?
H1A C1 H1B . . 114.9 ?
O4 N4 N3 . . 115.6(2) ?
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
N1 C4 . 1.346(2) ?
N1 C13 . 1.405(2) ?
N1 C3 . 1.466(2) ?
O2 C6 . 1.330(3) ?
O2 H18 . 0.8400 ?
O3 C7 . 1.273(2) ?
C8 C9 . 1.410(3) ?
C8 C13 . 1.411(3) ?
C8 C7 . 1.458(3) ?
F1 C10 . 1.365(2) ?
C13 C12 . 1.414(3) ?
C11 C12 . 1.394(3) ?
C11 N2 . 1.404(2) ?
C11 C10 . 1.420(3) ?
C5 C4 . 1.373(3) ?
C5 C7 . 1.431(3) ?
C5 C6 . 1.493(3) ?
O1 C6 . 1.210(3) ?
C12 H12A . 0.9500 ?
C9 C10 . 1.361(3) ?
C9 H9A . 0.9500 ?
N2 C14 . 1.469(3) ?
N2 C16 . 1.474(3) ?
C4 H4A . 0.9500 ?
N3 N4 . 1.315(3) ?
N3 C15 . 1.442(3) ?
N3 C17 . 1.456(3) ?
C3 C1 . 1.485(3) ?
C3 C2 . 1.485(3) ?
C3 H3A . 1.0000 ?
C14 C15 . 1.528(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C2 C1 . 1.501(3) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
C16 C17 . 1.496(3) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
C17 H17A . 0.9900 ?
C17 H17B . 0.9900 ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
N4 O4 . 1.238(3) ?
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
O2 H18 O3 . 0.84 1.78 2.562(2) 153.4
C4 H4A O1 . 0.95 2.48 2.812(3) 100.7
C15 H15A O2 1_666 0.99 2.50 3.405(3) 151.3
C15 H15B O3 2_665 0.99 2.51 3.385(3) 147.1
C16 H16A O1 2_565 0.99 2.60 3.264(3) 124.8
C16 H16B F1 . 0.99 2.14 2.852(3) 127.7
C17 H17B O4 . 0.99 2.30 2.692(3) 102.1
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24742969
