##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
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# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2004-01-05
_journal_date_accepted     2004-02-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2004
_journal_volume     60
_journal_issue      4
_journal_page_first     o503
_journal_page_last     o504
_journal_paper_category     EO
_publ_contact_author_name     'graduate Ke-Xia Lou'
_publ_contact_author_address
;
College of Pharmaceuticals and Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
_publ_contact_author_email     loukexia@126.com
_publ_contact_author_fax     '8622 2740 7558'
_publ_contact_author_phone     '8622 2740 1450'
_publ_section_title
;
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
;
loop_
    _publ_author_name
    _publ_author_address
    'Song, Jian'
;
College of Pharmaceuticals and Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Zhang, Shun-Xia'
;
College of Pharmaceuticals and Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
    'Lou, Ke-Xia'
;
College of Pharmaceuticals and Biotechnology
Tianjin University
Tianjin 300072
People's Republic of China
;
_publ_section_synopsis     ?
data_I
_chemical_name_systematic
;
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H9 Cl F N O3'
_chemical_formula_sum     'C13 H9 Cl F N O3'
_chemical_formula_iupac     'C13 H9 Cl F N O3'
_chemical_formula_weight     281.66
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 2 1 /n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     9.194(4)
_cell_length_b     7.515(4)
_cell_length_c     16.635(8)
_cell_angle_alpha     90.00
_cell_angle_beta     93.784(7)
_cell_angle_gamma     90.00
_cell_volume     1146.9(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     821
_cell_measurement_theta_min     2.61
_cell_measurement_theta_max     25.89
_cell_measurement_temperature     293(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.631
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     576
_exptl_absorpt_coefficient_mu     0.349
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     'SADABS (Bruker, 1997)'
_exptl_absorpt_correction_T_min     0.791
_exptl_absorpt_correction_T_max     0.939
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6311
_diffrn_reflns_av_R_equivalents     0.0274
_diffrn_reflns_av_sigmaI/netI     0.0320
_diffrn_reflns_theta_min     2.45
_diffrn_reflns_theta_max     26.44
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.992
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -20
_diffrn_reflns_limit_l_max     20
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
  Refinement of F² against ALL reflections.  The weighted R-factor wR and
  goodness of fit S are based on F², conventional R-factors R are based
  on F, with F set to zero for negative F². The threshold expression of
  F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
  not relevant to the choice of reflections for refinement.  R-factors based
  on F² are statistically about twice as large as those based on F, and R-
  factors based on ALL data will be even larger.
;
_reflns_number_total     2345
_reflns_number_gt     1753
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0608
_refine_ls_R_factor_gt     0.0398
_refine_ls_wR_factor_all     ?
_refine_ls_wR_factor_ref     0.0939
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     1.043
_refine_ls_restrained_S_all     1.043
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     2345
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.0523P)²+0.214P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.191
_refine_diff_density_min     -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1997)'
_computing_publication_material     'SHELXTL'
loop_
    _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
    _atom_site_type_symbol
    Cl1 -0.36322(5) 0.04973(9) 0.34750(3) 0.0538(2) Uani d . 1 . . Cl
    F1 -0.39000(13) 0.1174(2) 0.51629(8) 0.0611(4) Uani d . 1 . . F
    N1 0.16020(15) 0.2551(2) 0.42142(8) 0.0290(3) Uani d . 1 . . N
    O1 0.06637(16) 0.3536(2) 0.65430(8) 0.0501(4) Uani d . 1 . . O
    O2 0.33404(17) 0.4370(3) 0.68548(9) 0.0564(5) Uani d . 1 . . O
    H2 0.2473 0.4183 0.6906 0.085 Uiso calc R 1 . . H
    O3 0.48451(17) 0.4271(2) 0.58869(9) 0.0584(5) Uani d . 1 . . O
    C1 0.26346(19) 0.3120(2) 0.47639(10) 0.0304(4) Uani d . 1 . . C
    H1 0.3574 0.3278 0.4601 0.037 Uiso calc R 1 . . H
    C2 0.23837(19) 0.3480(3) 0.55496(10) 0.0319(4) Uani d . 1 . . C
    C3 0.0969(2) 0.3240(3) 0.58335(11) 0.0322(4) Uani d . 1 . . C
    C4 -0.01446(18) 0.2586(2) 0.52393(10) 0.0290(4) Uani d . 1 . . C
    C5 0.01861(18) 0.2253(2) 0.44408(10) 0.0277(4) Uani d . 1 . . C
    C6 -0.09057(19) 0.1603(3) 0.38843(11) 0.0326(4) Uani d . 1 . . C
    H6 -0.0703 0.1393 0.3352 0.039 Uiso calc R 1 . . H
    C7 -0.2268(2) 0.1286(3) 0.41347(12) 0.0356(5) Uani d . 1 . . C
    C8 -0.2578(2) 0.1585(3) 0.49335(12) 0.0381(5) Uani d . 1 . . C
    C9 -0.1548(2) 0.2244(3) 0.54756(11) 0.0358(5) Uani d . 1 . . C
    H9 -0.1775 0.2468 0.6003 0.043 Uiso calc R 1 . . H
    C10 0.3636(2) 0.4079(3) 0.60968(12) 0.0391(5) Uani d . 1 . . C
    C11 0.1978(2) 0.2062(3) 0.34043(10) 0.0320(4) Uani d . 1 . . C
    H11 0.2029 0.0782 0.3297 0.038 Uiso calc R 1 . . H
    C12 0.1426(2) 0.3186(3) 0.27074(11) 0.0390(5) Uani d . 1 . . C
    H12A 0.0858 0.4234 0.2821 0.047 Uiso calc R 1 . . H
    H12B 0.1135 0.2590 0.2205 0.047 Uiso calc R 1 . . H
    C13 0.3014(2) 0.3187(3) 0.29786(11) 0.0410(5) Uani d . 1 . . C
    H13A 0.3682 0.2593 0.2639 0.049 Uiso calc R 1 . . H
    H13B 0.3405 0.4237 0.3255 0.049 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    Cl1 0.0344(3) 0.0759(4) 0.0491(3) -0.0174(3) -0.0127(2) 0.0052(3)
    F1 0.0310(6) 0.0849(10) 0.0688(9) -0.0160(7) 0.0150(6) -0.0076(8)
    N1 0.0266(7) 0.0368(9) 0.0235(7) -0.0044(7) 0.0001(6) -0.0002(6)
    O1 0.0446(8) 0.0766(11) 0.0291(7) 0.0002(8) 0.0032(6) -0.0113(7)
    O2 0.0483(9) 0.0865(13) 0.0331(8) -0.0102(9) -0.0070(7) -0.0146(8)
    O3 0.0442(9) 0.0870(13) 0.0429(9) -0.0278(9) -0.0058(7) -0.0046(8)
    C1 0.0253(9) 0.0364(11) 0.0293(9) -0.0056(8) -0.0010(7) 0.0033(8)
    C2 0.0325(10) 0.0336(10) 0.0286(9) -0.0034(8) -0.0051(7) 0.0014(8)
    C3 0.0357(10) 0.0333(10) 0.0272(9) 0.0017(8) -0.0010(7) 0.0019(8)
    C4 0.0291(9) 0.0284(9) 0.0293(9) 0.0021(8) 0.0005(7) 0.0036(8)
    C5 0.0258(9) 0.0285(9) 0.0285(9) -0.0015(7) -0.0008(7) 0.0032(7)
    C6 0.0308(9) 0.0384(11) 0.0280(9) -0.0056(8) -0.0020(7) 0.0038(8)
    C7 0.0303(10) 0.0358(11) 0.0393(11) -0.0042(8) -0.0081(8) 0.0051(8)
    C8 0.0255(9) 0.0419(12) 0.0473(12) -0.0032(9) 0.0055(8) 0.0034(9)
    C9 0.0350(10) 0.0404(12) 0.0327(10) 0.0008(9) 0.0072(8) 0.0018(8)
    C10 0.0391(11) 0.0438(12) 0.0330(11) -0.0092(10) -0.0065(8) -0.0002(9)
    C11 0.0328(9) 0.0377(11) 0.0255(9) -0.0015(8) 0.0026(7) -0.0018(8)
    C12 0.0382(10) 0.0511(13) 0.0274(9) 0.0004(9) 0.0002(8) 0.0014(9)
    C13 0.0337(10) 0.0605(14) 0.0288(10) -0.0078(10) 0.0035(8) -0.0004(9)
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate (isotropic)
  treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
    Cl1 C7 . 1.7170(19) ?
    F1 C8 . 1.334(2) ?
    N1 C1 . 1.344(2) ?
    N1 C5 . 1.397(2) ?
    N1 C11 . 1.460(2) ?
    O1 C3 . 1.251(2) ?
    O2 C10 . 1.325(3) ?
    O2 H2 . 0.8200 ?
    O3 C10 . 1.196(2) ?
    C1 C2 . 1.369(3) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.424(3) ?
    C2 C10 . 1.490(3) ?
    C3 C4 . 1.461(2) ?
    C4 C9 . 1.397(3) ?
    C4 C5 . 1.404(2) ?
    C5 C6 . 1.407(2) ?
    C6 C7 . 1.366(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.396(3) ?
    C8 C9 . 1.358(3) ?
    C9 H9 . 0.9300 ?
    C11 C13 . 1.487(3) ?
    C11 C12 . 1.496(3) ?
    C11 H11 . 0.9800 ?
    C12 C13 . 1.500(3) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
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
    C1 N1 C5 . . 119.76(15) ?
    C1 N1 C11 . . 120.56(15) ?
    C5 N1 C11 . . 119.36(14) ?
    C10 O2 H2 . . 109.5 ?
    N1 C1 C2 . . 123.82(17) ?
    N1 C1 H1 . . 118.1 ?
    C2 C1 H1 . . 118.1 ?
    C1 C2 C3 . . 120.44(16) ?
    C1 C2 C10 . . 118.09(17) ?
    C3 C2 C10 . . 121.45(17) ?
    O1 C3 C2 . . 123.86(17) ?
    O1 C3 C4 . . 120.46(17) ?
    C2 C3 C4 . . 115.67(16) ?
    C9 C4 C5 . . 119.67(16) ?
    C9 C4 C3 . . 119.39(16) ?
    C5 C4 C3 . . 120.92(16) ?
    N1 C5 C4 . . 119.37(15) ?
    N1 C5 C6 . . 121.00(16) ?
    C4 C5 C6 . . 119.63(16) ?
    C7 C6 C5 . . 119.23(17) ?
    C7 C6 H6 . . 120.4 ?
    C5 C6 H6 . . 120.4 ?
    C6 C7 C8 . . 120.74(17) ?
    C6 C7 Cl1 . . 120.74(15) ?
    C8 C7 Cl1 . . 118.51(15) ?
    F1 C8 C9 . . 120.24(18) ?
    F1 C8 C7 . . 118.85(17) ?
    C9 C8 C7 . . 120.90(18) ?
    C8 C9 C4 . . 119.80(18) ?
    C8 C9 H9 . . 120.1 ?
    C4 C9 H9 . . 120.1 ?
    O3 C10 O2 . . 120.73(18) ?
    O3 C10 C2 . . 123.66(19) ?
    O2 C10 C2 . . 115.61(18) ?
    N1 C11 C13 . . 119.62(16) ?
    N1 C11 C12 . . 118.95(17) ?
    C13 C11 C12 . . 60.35(13) ?
    N1 C11 H11 . . 115.6 ?
    C13 C11 H11 . . 115.6 ?
    C12 C11 H11 . . 115.6 ?
    C11 C12 C13 . . 59.54(12) ?
    C11 C12 H12A . . 117.8 ?
    C13 C12 H12A . . 117.8 ?
    C11 C12 H12B . . 117.8 ?
    C13 C12 H12B . . 117.8 ?
    H12A C12 H12B . . 115.0 ?
    C11 C13 C12 . . 60.11(12) ?
    C11 C13 H13A . . 117.8 ?
    C12 C13 H13A . . 117.8 ?
    C11 C13 H13B . . 117.8 ?
    C12 C13 H13B . . 117.8 ?
    H13A C13 H13B . . 114.9 ?
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
    C5 N1 C1 C2 . . . . -1.6(3) ?
    C11 N1 C1 C2 . . . . -175.17(18) ?
    N1 C1 C2 C3 . . . . 0.8(3) ?
    N1 C1 C2 C10 . . . . 179.19(18) ?
    C1 C2 C3 O1 . . . . 179.74(19) ?
    C10 C2 C3 O1 . . . . 1.4(3) ?
    C1 C2 C3 C4 . . . . 0.5(3) ?
    C10 C2 C3 C4 . . . . -177.85(17) ?
    O1 C3 C4 C9 . . . . -1.8(3) ?
    C2 C3 C4 C9 . . . . 177.42(17) ?
    O1 C3 C4 C5 . . . . 179.83(18) ?
    C2 C3 C4 C5 . . . . -0.9(3) ?
    C1 N1 C5 C4 . . . . 1.2(3) ?
    C11 N1 C5 C4 . . . . 174.77(16) ?
    C1 N1 C5 C6 . . . . -177.97(18) ?
    C11 N1 C5 C6 . . . . -4.4(3) ?
    C9 C4 C5 N1 . . . . -178.24(16) ?
    C3 C4 C5 N1 . . . . 0.1(3) ?
    C9 C4 C5 C6 . . . . 0.9(3) ?
    C3 C4 C5 C6 . . . . 179.26(17) ?
    N1 C5 C6 C7 . . . . 178.31(17) ?
    C4 C5 C6 C7 . . . . -0.8(3) ?
    C5 C6 C7 C8 . . . . -0.5(3) ?
    C5 C6 C7 Cl1 . . . . 179.88(15) ?
    C6 C7 C8 F1 . . . . -176.66(18) ?
    Cl1 C7 C8 F1 . . . . 3.0(3) ?
    C6 C7 C8 C9 . . . . 1.8(3) ?
    Cl1 C7 C8 C9 . . . . -178.58(16) ?
    F1 C8 C9 C4 . . . . 176.74(18) ?
    C7 C8 C9 C4 . . . . -1.7(3) ?
    C5 C4 C9 C8 . . . . 0.3(3) ?
    C3 C4 C9 C8 . . . . -178.03(18) ?
    C1 C2 C10 O3 . . . . 0.4(3) ?
    C3 C2 C10 O3 . . . . 178.8(2) ?
    C1 C2 C10 O2 . . . . -178.50(19) ?
    C3 C2 C10 O2 . . . . -0.1(3) ?
    C1 N1 C11 C13 . . . . -42.2(3) ?
    C5 N1 C11 C13 . . . . 144.20(17) ?
    C1 N1 C11 C12 . . . . -112.6(2) ?
    C5 N1 C11 C12 . . . . 73.8(2) ?
    N1 C11 C12 C13 . . . . 109.58(19) ?
    N1 C11 C13 C12 . . . . -108.5(2) ?
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
    _geom_hbond_publ_flag
    O2 H2 O1 . 0.82 1.80 2.559(2) 154 Y
    O2 H2 Cl1 4_666 0.82 2.87 3.348(2) 119 Y
