#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:05:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179612 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507627.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_4507627
loop_
_publ_author_name
'Karanam, Maheswararao'
'Choudhury, Angshuman Roy'
_publ_section_title
;
 Structural Landscape of Pure Enrofloxacin and Its Novel Salts: Enhanced
 Solubility for Better Pharmaceutical Applicability
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1626
_journal_paper_doi               10.1021/cg301831s
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C19 H23 F N3 O3, C2 H2 O2, C2 H O2'
_chemical_formula_sum            'C23 H26 F N3 O7'
_chemical_formula_weight         475.47
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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_date             2012-10-29T20:08:21-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                119.469(4)
_cell_angle_beta                 100.139(5)
_cell_angle_gamma                92.049(6)
_cell_formula_units_Z            2
_cell_length_a                   6.9067(7)
_cell_length_b                   13.4563(14)
_cell_length_c                   13.6479(13)
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      3.03
_cell_volume                     1075.93(19)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_computing_structure_solution
;
        SHELXS, G.M. Sheldrick, Acta Cryst.
        (2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11458
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.03
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.6934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0507 before and 0.0367 after correction.
        The Ratio of minimum to maximum transmission is 0.9295.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     320
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.4250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                3345
_reflns_number_total             4233
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301831s_si_010.cif
_cod_data_source_block           a22f0511100k_0m
_cod_database_code               4507627
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'
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_calc_flag
_atom_site_refinement_flags
C19 C 1.1609(3) 0.81668(15) 0.53659(14) 0.0266(4) Uani 1 1 d .
H19A H 1.2231 0.7985 0.4716 0.04 Uiso 1 1 calc R
H19B H 1.2643 0.8426 0.6067 0.04 Uiso 1 1 calc R
H19C H 1.0792 0.878 0.5479 0.04 Uiso 1 1 calc R
C18 C 1.0320(3) 0.71070(14) 0.51133(14) 0.0246(4) Uani 1 1 d .
H18A H 0.9366 0.6807 0.4364 0.029 Uiso 1 1 calc R
H18B H 1.1167 0.6506 0.5039 0.029 Uiso 1 1 calc R
C7 C 0.8096(2) 0.60367(13) 0.99063(13) 0.0169(3) Uani 1 1 d .
C16 C 1.0538(2) 0.76025(14) 0.71423(13) 0.0200(3) Uani 1 1 d .
H16A H 1.1432 0.8331 0.7447 0.024 Uiso 1 1 calc R
H16B H 1.1371 0.6982 0.7002 0.024 Uiso 1 1 calc R
C8 C 0.7298(2) 0.48601(13) 0.92835(13) 0.0172(3) Uani 1 1 d .
C17 C 0.9368(2) 0.77264(14) 0.80365(13) 0.0219(4) Uani 1 1 d .
H17A H 1.0286 0.7853 0.8745 0.026 Uiso 1 1 calc R
H17B H 0.8637 0.8397 0.8244 0.026 Uiso 1 1 calc R
C5 C 0.7756(2) 0.61063(14) 0.81394(13) 0.0186(3) Uani 1 1 d .
C6 C 0.8326(2) 0.66483(13) 0.93371(13) 0.0181(3) Uani 1 1 d .
H6 H 0.8876 0.7441 0.9774 0.022 Uiso 1 1 calc R
C9 C 0.8380(2) 0.60189(13) 1.16603(13) 0.0173(3) Uani 1 1 d .
H9 H 0.8764 0.6424 1.2479 0.021 Uiso 1 1 calc R
C1 C 0.7607(2) 0.48718(13) 1.11033(13) 0.0178(3) Uani 1 1 d .
C10 C 0.7378(2) 0.43231(13) 1.18027(13) 0.0190(3) Uani 1 1 d .
C2 C 0.7019(2) 0.42254(13) 0.98657(13) 0.0180(3) Uani 1 1 d .
C3 C 0.6777(2) 0.43015(14) 0.80699(13) 0.0188(3) Uani 1 1 d .
H3 H 0.6254 0.3505 0.7626 0.023 Uiso 1 1 calc R
C4 C 0.7028(2) 0.49120(14) 0.75390(13) 0.0190(3) Uani 1 1 d .
C15 C 0.7626(2) 0.63147(14) 0.55932(13) 0.0215(4) Uani 1 1 d .
H15A H 0.8253 0.5604 0.5351 0.026 Uiso 1 1 calc R
H15B H 0.6666 0.622 0.4913 0.026 Uiso 1 1 calc R
C14 C 0.6537(2) 0.64894(14) 0.65314(13) 0.0213(4) Uani 1 1 d .
H14A H 0.582 0.7164 0.6734 0.026 Uiso 1 1 calc R
H14B H 0.5552 0.5801 0.6249 0.026 Uiso 1 1 calc R
C11 C 0.9543(2) 0.78106(13) 1.17694(13) 0.0193(3) Uani 1 1 d .
H11 H 1.0913 0.7961 1.1682 0.023 Uiso 1 1 calc R
C13 C 0.9119(3) 0.85964(14) 1.29263(14) 0.0246(4) Uani 1 1 d .
H13A H 1.0209 0.9195 1.353 0.03 Uiso 1 1 calc R
H13B H 0.8209 0.8269 1.3214 0.03 Uiso 1 1 calc R
C12 C 0.8248(3) 0.87215(14) 1.19047(14) 0.0245(4) Uani 1 1 d .
H12A H 0.6806 0.847 1.1567 0.029 Uiso 1 1 calc R
H12B H 0.8807 0.9396 1.1883 0.029 Uiso 1 1 calc R
N3 N 0.9186(2) 0.73237(12) 0.60254(11) 0.0183(3) Uani 1 1 d .
N2 N 0.7977(2) 0.66755(12) 0.75460(11) 0.0230(3) Uani 1 1 d .
N1 N 0.86249(19) 0.66011(11) 1.11156(10) 0.0172(3) Uani 1 1 d .
O1 O 0.66372(17) 0.32085(9) 1.11921(10) 0.0227(3) Uani 1 1 d .
O2 O 0.78272(17) 0.48311(10) 1.28517(9) 0.0250(3) Uani 1 1 d .
O3 O 0.62982(16) 0.31665(9) 0.93080(9) 0.0222(3) Uani 1 1 d .
F1 F 0.66309(14) 0.43354(8) 0.63629(7) 0.0238(2) Uani 1 1 d .
C20 C 0.3523(3) 0.96836(14) 0.09231(14) 0.0242(4) Uani 1 1 d .
C21 C 0.4386(2) 0.95878(14) -0.00432(14) 0.0232(4) Uani 1 1 d .
H21 H 0.4027 0.8889 -0.0765 0.028 Uiso 1 1 calc R
O4 O 0.45641(18) 1.04625(10) 0.19576(10) 0.0267(3) Uani 1 1 d .
O5 O 0.1981(2) 0.91073(11) 0.07522(10) 0.0365(3) Uani 1 1 d .
C22 C 0.3646(2) 1.10365(14) 0.46031(13) 0.0191(3) Uani 1 1 d .
C23 C 0.4625(2) 1.00328(14) 0.45372(14) 0.0213(4) Uani 1 1 d .
H23 H 0.4711 0.942 0.3801 0.026 Uiso 1 1 calc R
O6 O 0.28343(17) 1.09191(10) 0.36120(9) 0.0229(3) Uani 1 1 d .
O7 O 0.36083(17) 1.18855(10) 0.55361(9) 0.0255(3) Uani 1 1 d .
H1 H 0.639(4) 0.302(2) 1.043(2) 0.063(7) Uiso 1 1 d .
H4 H 0.377(4) 1.050(2) 0.259(2) 0.083(9) Uiso 1 1 d .
H3A H 0.856(3) 0.7976(19) 0.6184(18) 0.046(6) Uiso 1 1 d .
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 0 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
H19A C19 H19B 109.5 .
H19A C19 H19C 109.5 .
H19B C19 H19C 109.5 .
C18 C19 H19A 109.5 .
C18 C19 H19B 109.5 .
C18 C19 H19C 109.5 .
C19 C18 H18A 108.9 .
C19 C18 H18B 108.9 .
H18A C18 H18B 107.7 .
N3 C18 C19 113.28(13) .
N3 C18 H18A 108.9 .
N3 C18 H18B 108.9 .
C6 C7 C8 121.00(14) .
N1 C7 C8 118.85(13) .
N1 C7 C6 120.13(14) .
H16A C16 H16B 108 .
C17 C16 H16A 109.3 .
C17 C16 H16B 109.3 .
N3 C16 H16A 109.3 .
N3 C16 H16B 109.3 .
N3 C16 C17 111.54(13) .
C7 C8 C2 121.42(14) .
C7 C8 C3 118.37(14) .
C3 C8 C2 120.21(14) .
C16 C17 H17A 110 .
C16 C17 H17B 110 .
H17A C17 H17B 108.4 .
N2 C17 C16 108.49(13) .
N2 C17 H17A 110 .
N2 C17 H17B 110 .
C6 C5 C4 116.67(14) .
N2 C5 C6 122.45(14) .
N2 C5 C4 120.78(13) .
C7 C6 H6 119.6 .
C5 C6 C7 120.71(14) .
C5 C6 H6 119.6 .
C1 C9 H9 118.1 .
N1 C9 H9 118.1 .
N1 C9 C1 123.89(14) .
C9 C1 C10 119.01(13) .
C9 C1 C2 119.89(14) .
C2 C1 C10 121.10(14) .
O1 C10 C1 114.91(13) .
O2 C10 C1 123.94(14) .
O2 C10 O1 121.14(14) .
C1 C2 C8 115.86(14) .
O3 C2 C8 121.60(14) .
O3 C2 C1 122.54(14) .
C8 C3 H3 120.3 .
C4 C3 C8 119.44(15) .
C4 C3 H3 120.3 .
C3 C4 C5 123.71(14) .
C3 C4 F1 118.24(14) .
F1 C4 C5 117.99(13) .
H15A C15 H15B 108.1 .
C14 C15 H15A 109.5 .
C14 C15 H15B 109.5 .
N3 C15 H15A 109.5 .
N3 C15 H15B 109.5 .
N3 C15 C14 110.50(12) .
C15 C14 H14A 109.9 .
C15 C14 H14B 109.9 .
H14A C14 H14B 108.3 .
N2 C14 C15 109.02(13) .
N2 C14 H14A 109.9 .
N2 C14 H14B 109.9 .
C13 C11 H11 115.7 .
C13 C11 C12 60.48(11) .
C12 C11 H11 115.7 .
N1 C11 H11 115.7 .
N1 C11 C13 119.48(13) .
N1 C11 C12 118.58(14) .
C11 C13 H13A 117.8 .
C11 C13 H13B 117.8 .
C11 C13 C12 59.88(10) .
H13A C13 H13B 114.9 .
C12 C13 H13A 117.8 .
C12 C13 H13B 117.8 .
C11 C12 C13 59.64(10) .
C11 C12 H12A 117.8 .
C11 C12 H12B 117.8 .
C13 C12 H12A 117.8 .
C13 C12 H12B 117.8 .
H12A C12 H12B 114.9 .
C18 N3 H3A 108.7(13) .
C16 N3 C18 111.75(12) .
C16 N3 H3A 105.9(13) .
C15 N3 C18 109.75(12) .
C15 N3 C16 112.05(12) .
C15 N3 H3A 108.5(13) .
C17 N2 C14 111.60(12) .
C5 N2 C17 122.61(13) .
C5 N2 C14 123.89(13) .
C7 N1 C11 119.29(12) .
C9 N1 C7 120.09(13) .
C9 N1 C11 120.53(12) .
C10 O1 H1 105.9(15) .
O4 C20 C21 113.94(15) .
O5 C20 C21 121.97(15) .
O5 C20 O4 124.07(15) .
C20 C21 H21 118 .
C21 C21 C20 124.03(19) 2_675
C21 C21 H21 118 2_675
C20 O4 H4 108.2(14) .
O6 C22 C23 114.89(13) .
O7 C22 C23 121.31(14) .
O7 C22 O6 123.79(14) .
C22 C23 H23 118.6 .
C23 C23 C22 122.73(19) 2_676
C23 C23 H23 118.6 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C19 H19A 0.98 .
C19 H19B 0.98 .
C19 H19C 0.98 .
C19 C18 1.504(2) .
C18 H18A 0.99 .
C18 H18B 0.99 .
C18 N3 1.500(2) .
C7 C8 1.408(2) .
C7 C6 1.403(2) .
C7 N1 1.4031(19) .
C16 H16A 0.99 .
C16 H16B 0.99 .
C16 C17 1.525(2) .
C16 N3 1.4991(19) .
C8 C2 1.452(2) .
C8 C3 1.409(2) .
C17 H17A 0.99 .
C17 H17B 0.99 .
C17 N2 1.455(2) .
C5 C6 1.392(2) .
C5 C4 1.417(2) .
C5 N2 1.3825(19) .
C6 H6 0.95 .
C9 H9 0.95 .
C9 C1 1.375(2) .
C9 N1 1.3425(19) .
C1 C10 1.490(2) .
C1 C2 1.436(2) .
C10 O1 1.3308(19) .
C10 O2 1.2159(18) .
C2 O3 1.2674(18) .
C3 H3 0.95 .
C3 C4 1.360(2) .
C4 F1 1.3632(17) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C15 C14 1.522(2) .
C15 N3 1.495(2) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C14 N2 1.4580(19) .
C11 H11 1 .
C11 C13 1.496(2) .
C11 C12 1.500(2) .
C11 N1 1.4647(19) .
C13 H13A 0.99 .
C13 H13B 0.99 .
C13 C12 1.509(2) .
C12 H12A 0.99 .
C12 H12B 0.99 .
N3 H3A 0.94(2) .
O1 H1 0.92(2) .
C20 C21 1.492(2) .
C20 O4 1.320(2) .
C20 O5 1.211(2) .
C21 C21 1.316(3) 2_675
C21 H21 0.95 .
O4 H4 1.08(3) .
C22 C23 1.503(2) .
C22 O6 1.2982(18) .
C22 O7 1.2287(19) .
C23 C23 1.324(3) 2_676
C23 H23 0.95 .
