#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:05:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179612 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507625.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_4507625
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 H3 O2, C2 H2 O2'
_chemical_formula_sum            'C23 H28 F N3 O7'
_chemical_formula_weight         477.48
_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             2012-10-29T23:09:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                119.633(8)
_cell_angle_beta                 90.036(9)
_cell_angle_gamma                101.663(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0383(19)
_cell_length_b                   13.397(4)
_cell_length_c                   13.513(4)
_cell_measurement_reflns_used    1907
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.63
_cell_measurement_theta_min      2.98
_cell_volume                     1077.1(5)
_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_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10667
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         1.75
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.5758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0933 before and 0.0674 after correction.
        The Ratio of minimum to maximum transmission is 0.7716.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATE
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.037(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.948
_refine_ls_R_factor_all          0.1525
_refine_ls_R_factor_gt           0.0776
_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)+(0.1258P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.2226
_reflns_number_gt                1970
_reflns_number_total             3787
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301831s_si_007.cif
_cod_data_source_block           a22f20_100k_0m
_cod_original_cell_volume        1077.0(5)
_cod_database_code               4507625
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 0.6699(7) 0.0298(5) 0.2219(4) 0.0417(13) Uani 1 1 d .
H19A H 0.7219 -0.0396 0.1739 0.063 Uiso 1 1 calc R
H19B H 0.7782 0.0978 0.269 0.063 Uiso 1 1 calc R
H19C H 0.5963 0.0472 0.1729 0.063 Uiso 1 1 calc R
C18 C 0.5365(7) 0.0054(4) 0.2988(4) 0.0405(13) Uani 1 1 d .
H18A H 0.4383 -0.0695 0.2509 0.049 Uiso 1 1 calc R
H18B H 0.6147 -0.0056 0.352 0.049 Uiso 1 1 calc R
C15 C 0.2677(7) 0.0550(4) 0.4139(4) 0.0326(11) Uani 1 1 d .
H15A H 0.318 0.0262 0.4612 0.039 Uiso 1 1 calc R
H15B H 0.1745 -0.0123 0.3498 0.039 Uiso 1 1 calc R
C14 C 0.1646(7) 0.1501(4) 0.4854(4) 0.0329(12) Uani 1 1 d .
H14A H 0.1012 0.1725 0.4363 0.04 Uiso 1 1 calc R
H14B H 0.0617 0.1204 0.5206 0.04 Uiso 1 1 calc R
C5 C 0.2777(6) 0.3097(4) 0.6905(3) 0.0277(11) Uani 1 1 d .
C4 C 0.1973(6) 0.2427(4) 0.7421(4) 0.0301(11) Uani 1 1 d .
C3 C 0.1707(6) 0.2930(4) 0.8542(3) 0.0295(11) Uani 1 1 d .
H3 H 0.1148 0.2449 0.8848 0.035 Uiso 1 1 calc R
C8 C 0.2253(6) 0.4157(4) 0.9253(3) 0.0278(11) Uani 1 1 d .
C2 C 0.1987(6) 0.4714(4) 1.0458(4) 0.0278(11) Uani 1 1 d .
C1 C 0.2591(6) 0.5961(4) 1.1109(3) 0.0287(11) Uani 1 1 d .
C10 C 0.2366(7) 0.6632(5) 1.2343(4) 0.0302(11) Uani 1 1 d .
C16 C 0.5645(6) 0.2110(4) 0.4574(3) 0.0316(11) Uani 1 1 d .
H16A H 0.6615 0.2427 0.4208 0.038 Uiso 1 1 calc R
H16B H 0.6364 0.1934 0.5077 0.038 Uiso 1 1 calc R
C17 C 0.4546(7) 0.3024(4) 0.5285(4) 0.0342(12) Uani 1 1 d .
H17A H 0.5449 0.3723 0.5918 0.041 Uiso 1 1 calc R
H17B H 0.3957 0.3279 0.4807 0.041 Uiso 1 1 calc R
C6 C 0.3359(6) 0.4307(4) 0.7610(4) 0.0318(11) Uani 1 1 d .
H6 H 0.3955 0.4778 0.7301 0.038 Uiso 1 1 calc R
C7 C 0.3087(6) 0.4850(4) 0.8768(3) 0.0280(11) Uani 1 1 d .
C9 C 0.3353(6) 0.6589(4) 1.0586(4) 0.0297(11) Uani 1 1 d .
H9 H 0.3712 0.7427 1.1036 0.036 Uiso 1 1 calc R
C11 C 0.4443(7) 0.6811(4) 0.8985(3) 0.0301(11) Uani 1 1 d .
H11 H 0.5821 0.6809 0.8804 0.036 Uiso 1 1 calc R
C12 C 0.3830(7) 0.7942(4) 0.9365(4) 0.0349(12) Uani 1 1 d .
H12A H 0.289 0.8154 0.9939 0.042 Uiso 1 1 calc R
H12B H 0.4818 0.862 0.9431 0.042 Uiso 1 1 calc R
C13 C 0.3100(7) 0.6912(4) 0.8189(4) 0.0347(12) Uani 1 1 d .
H13A H 0.364 0.6954 0.753 0.042 Uiso 1 1 calc R
H13B H 0.1712 0.6488 0.8039 0.042 Uiso 1 1 calc R
C20 C 1.0966(7) 0.3768(5) 0.3819(4) 0.0368(12) Uani 1 1 d .
C21 C 1.0882(7) 0.4977(4) 0.4670(4) 0.0439(13) Uani 1 1 d .
H21A H 1.0833 0.5431 0.4277 0.053 Uiso 1 1 calc R
H21B H 1.2089 0.5359 0.5218 0.053 Uiso 1 1 calc R
N3 N 0.4324(6) 0.1003(4) 0.3673(3) 0.0322(11) Uani 1 1 d .
N2 N 0.3026(5) 0.2529(3) 0.5748(3) 0.0356(10) Uani 1 1 d .
N1 N 0.3612(5) 0.6074(3) 0.9470(3) 0.0270(9) Uani 1 1 d .
O1 O 0.1598(5) 0.5964(3) 1.2783(3) 0.0360(9) Uani 1 1 d .
O2 O 0.2860(5) 0.7702(3) 1.2936(2) 0.0380(9) Uani 1 1 d .
O3 O 0.1247(4) 0.4087(3) 1.0895(2) 0.0352(8) Uani 1 1 d .
O4 O 0.9739(5) 0.2874(3) 0.3674(3) 0.0524(10) Uani 1 1 d .
O5 O 1.2471(5) 0.3672(3) 0.3206(3) 0.0442(9) Uani 1 1 d .
H5 H 1.2666 0.2991 0.293 0.066 Uiso 1 1 calc R
F1 F 0.1525(4) 0.1233(2) 0.6769(2) 0.0355(7) Uani 1 1 d .
C22 C -0.1620(6) -0.0531(4) 0.8569(4) 0.0274(11) Uani 1 1 d .
C23 C -0.0524(6) -0.0605(4) 0.9504(3) 0.0321(12) Uani 1 1 d .
H23A H -0.1465 -0.1013 0.9807 0.039 Uiso 1 1 calc R
H23B H 0.0447 -0.1085 0.9159 0.039 Uiso 1 1 calc R
O6 O -0.2777(4) -0.1517(3) 0.7806(2) 0.0328(8) Uani 1 1 d .
O7 O -0.1390(5) 0.0401(3) 0.8566(2) 0.0379(9) Uani 1 1 d .
H1 H 0.134(8) 0.516(5) 1.217(5) 0.066(18) Uiso 1 1 d .
H3A H 0.406(6) 0.119(4) 0.329(4) 0.016(13) 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
_geom_angle_site_symmetry_3
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 108.7 . .
C19 C18 H18B 108.7 . .
H18A C18 H18B 107.6 . .
N3 C18 C19 114.2(4) . .
N3 C18 H18A 108.7 . .
N3 C18 H18B 108.7 . .
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 110.5(4) . .
C15 C14 H14A 109.6 . .
C15 C14 H14B 109.6 . .
H14A C14 H14B 108.1 . .
N2 C14 C15 110.2(4) . .
N2 C14 H14A 109.6 . .
N2 C14 H14B 109.6 . .
C6 C5 C4 117.2(4) . .
C6 C5 N2 122.6(4) . .
N2 C5 C4 120.2(4) . .
C3 C4 C5 122.8(4) . .
C3 C4 F1 118.6(4) . .
F1 C4 C5 118.5(4) . .
C4 C3 H3 119.9 . .
C4 C3 C8 120.1(4) . .
C8 C3 H3 119.9 . .
C3 C8 C2 121.0(4) . .
C3 C8 C7 118.5(4) . .
C7 C8 C2 120.5(4) . .
C1 C2 C8 116.9(4) . .
O3 C2 C8 120.4(4) . .
O3 C2 C1 122.8(4) . .
C2 C1 C10 121.9(4) . .
C9 C1 C2 120.1(4) . .
C9 C1 C10 118.0(4) . .
O1 C10 C1 114.5(4) . .
O2 C10 C1 124.3(4) . .
O2 C10 O1 121.2(4) . .
H16A C16 H16B 107.9 . .
C17 C16 H16A 109.3 . .
C17 C16 H16B 109.3 . .
N3 C16 H16A 109.3 . .
N3 C16 H16B 109.3 . .
N3 C16 C17 111.8(3) . .
C16 C17 H17A 109.8 . .
C16 C17 H17B 109.8 . .
H17A C17 H17B 108.3 . .
N2 C17 C16 109.2(4) . .
N2 C17 H17A 109.8 . .
N2 C17 H17B 109.8 . .
C5 C6 H6 119.4 . .
C5 C6 C7 121.2(4) . .
C7 C6 H6 119.4 . .
C6 C7 C8 120.2(4) . .
N1 C7 C8 118.7(4) . .
N1 C7 C6 121.1(4) . .
C1 C9 H9 118.4 . .
N1 C9 C1 123.1(4) . .
N1 C9 H9 118.4 . .
C12 C11 H11 116.3 . .
C12 C11 C13 59.8(3) . .
C13 C11 H11 116.3 . .
N1 C11 H11 116.3 . .
N1 C11 C12 118.6(4) . .
N1 C11 C13 117.7(4) . .
C11 C12 H12A 117.7 . .
C11 C12 H12B 117.7 . .
H12A C12 H12B 114.9 . .
C13 C12 C11 60.4(3) . .
C13 C12 H12A 117.7 . .
C13 C12 H12B 117.7 . .
C11 C13 H13A 117.8 . .
C11 C13 H13B 117.8 . .
C12 C13 C11 59.8(3) . .
C12 C13 H13A 117.8 . .
C12 C13 H13B 117.8 . .
H13A C13 H13B 114.9 . .
O4 C20 C21 123.3(5) . .
O4 C20 O5 121.4(5) . .
O5 C20 C21 115.3(5) . .
C20 C21 C21 112.6(6) . 2_766
C20 C21 H21A 109.1 . .
C20 C21 H21B 109.1 . .
C21 C21 H21A 109.1 2_766 .
C21 C21 H21B 109.1 2_766 .
H21A C21 H21B 107.8 . .
C18 N3 H3A 105(3) . .
C15 N3 C18 109.8(4) . .
C15 N3 H3A 116(4) . .
C16 N3 C18 113.1(4) . .
C16 N3 C15 112.6(3) . .
C16 N3 H3A 101(4) . .
C5 N2 C14 124.5(4) . .
C5 N2 C17 122.4(4) . .
C17 N2 C14 112.3(3) . .
C7 N1 C11 119.8(3) . .
C9 N1 C7 120.7(4) . .
C9 N1 C11 119.5(4) . .
C10 O1 H1 107(3) . .
C20 O5 H5 109.5 . .
O6 C22 C23 114.7(4) . .
O7 C22 C23 121.2(4) . .
O7 C22 O6 124.1(4) . .
C22 C23 H23A 109 . .
C22 C23 H23B 109 . .
C23 C23 C22 113.0(4) 2_557 .
C23 C23 H23A 109 2_557 .
C23 C23 H23B 109 2_557 .
H23A C23 H23B 107.8 . .
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 1.511(6) .
C18 H18A 0.99 .
C18 H18B 0.99 .
C18 N3 1.491(6) .
C15 H15A 0.99 .
C15 H15B 0.99 .
C15 C14 1.497(6) .
C15 N3 1.484(6) .
C14 H14A 0.99 .
C14 H14B 0.99 .
C14 N2 1.453(6) .
C5 C4 1.422(6) .
C5 C6 1.381(6) .
C5 N2 1.390(5) .
C4 C3 1.352(6) .
C4 F1 1.355(5) .
C3 H3 0.95 .
C3 C8 1.398(6) .
C8 C2 1.450(6) .
C8 C7 1.419(6) .
C2 C1 1.416(6) .
C2 O3 1.279(5) .
C1 C10 1.479(6) .
C1 C9 1.380(6) .
C10 O1 1.333(5) .
C10 O2 1.217(5) .
C16 H16A 0.99 .
C16 H16B 0.99 .
C16 C17 1.497(6) .
C16 N3 1.484(6) .
C17 H17A 0.99 .
C17 H17B 0.99 .
C17 N2 1.449(5) .
C6 H6 0.95 .
C6 C7 1.395(6) .
C7 N1 1.394(5) .
C9 H9 0.95 .
C9 N1 1.344(5) .
C11 H11 1 .
C11 C12 1.496(6) .
C11 C13 1.504(6) .
C11 N1 1.467(5) .
C12 H12A 0.99 .
C12 H12B 0.99 .
C12 C13 1.495(6) .
C13 H13A 0.99 .
C13 H13B 0.99 .
C20 C21 1.465(7) .
C20 O4 1.252(6) .
C20 O5 1.332(5) .
C21 C21 1.523(9) 2_766
C21 H21A 0.99 .
C21 H21B 0.99 .
N3 H3A 0.71(4) .
O1 H1 0.96(6) .
O5 H5 0.84 .
C22 C23 1.535(6) .
C22 O6 1.299(5) .
C22 O7 1.228(5) .
C23 C23 1.528(9) 2_557
C23 H23A 0.99 .
C23 H23B 0.99 .
