#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:05:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179612 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/76/4507624.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_4507624
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, 3(H2 O), C O2'
_chemical_formula_sum            'C20 H29 F N3 O8'
_chemical_formula_weight         458.46
_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             2012-10-29T19:54:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                85.137(3)
_cell_angle_beta                 83.594(3)
_cell_angle_gamma                73.497(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0198(10)
_cell_length_b                   9.3767(19)
_cell_length_c                   17.249(4)
_cell_measurement_reflns_used    572
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.75
_cell_measurement_theta_min      2.62
_cell_volume                     1080.1(4)
_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 0.929
_diffrn_measured_fraction_theta_max 0.929
_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  0.0166
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4527
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.27
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        wR2(int) was 0.0377 before and 0.0275 after correction.
        The Ratio of minimum to maximum transmission is 0.8701.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.41
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.05
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.5456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1223
_reflns_number_gt                2493
_reflns_number_total             3409
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg301831s_si_006.cif
_cod_data_source_block           a22f2211_100k_0m
_cod_database_code               4507624
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
F1 F 0.1630(2) 0.49376(15) 0.06919(8) 0.0260(4) Uani 1 1 d .
O2 O 0.3333(3) -0.3434(2) -0.11193(11) 0.0327(5) Uani 1 1 d .
O8 O -0.1668(4) -0.1303(2) 0.33514(12) 0.0476(6) Uani 1 1 d G
H8A H -0.1428 -0.1344 0.2847 0.071 Uiso 1 1 d G
H8B H -0.1386 -0.2203 0.3567 0.071 Uiso 1 1 d G
O7 O 0.1083(4) -0.0792(2) 0.43625(16) 0.0599(7) Uani 1 1 d G
H7A H 0.0433 -0.0649 0.3949 0.09 Uiso 1 1 d G
H7B H 0.1103 -0.1663 0.4586 0.09 Uiso 1 1 d G
O1 O 0.2995(3) -0.1376(2) -0.18946(10) 0.0286(5) Uani 1 1 d .
O6 O 0.4615(4) 0.0048(3) 0.42063(16) 0.0643(7) Uani 1 1 d G
H6A H 0.3686 -0.0408 0.4246 0.096 Uiso 1 1 d G
H6B H 0.5693 -0.0497 0.3962 0.096 Uiso 1 1 d G
N1 N 0.2600(3) -0.1120(2) 0.08806(11) 0.0194(5) Uani 1 1 d .
N3 N -0.1664(3) 0.3629(2) 0.34031(12) 0.0205(5) Uani 1 1 d .
O3 O 0.2355(3) 0.11264(19) -0.12746(9) 0.0243(4) Uani 1 1 d .
C10 C 0.3066(4) -0.2091(3) -0.11905(15) 0.0244(6) Uani 1 1 d .
C1 C 0.2796(4) -0.1150(3) -0.05164(14) 0.0210(6) Uani 1 1 d .
C9 C 0.2811(4) -0.1831(3) 0.02201(14) 0.0205(6) Uani 1 1 d .
H9 H 0.2983 -0.2876 0.0265 0.025 Uiso 1 1 calc R
C7 C 0.2319(3) 0.0427(3) 0.08358(14) 0.0178(5) Uani 1 1 d .
C6 C 0.2036(4) 0.1193(3) 0.15184(14) 0.0191(5) Uani 1 1 d .
H6 H 0.2045 0.0653 0.201 0.023 Uiso 1 1 calc R
C5 C 0.1740(4) 0.2730(3) 0.14960(14) 0.0193(6) Uani 1 1 d .
N2 N 0.1553(3) 0.3514(2) 0.21656(11) 0.0200(5) Uani 1 1 d .
C14 C -0.0087(4) 0.4884(3) 0.22843(15) 0.0220(6) Uani 1 1 d .
H14A H -0.0344 0.5434 0.1774 0.026 Uiso 1 1 calc R
H14B H 0.0321 0.5528 0.2621 0.026 Uiso 1 1 calc R
C15 C -0.1999(4) 0.4565(3) 0.26582(14) 0.0214(6) Uani 1 1 d .
H15A H -0.3018 0.5518 0.2766 0.026 Uiso 1 1 calc R
H15B H -0.2514 0.4042 0.2289 0.026 Uiso 1 1 calc R
C18 C -0.3494(4) 0.3214(3) 0.37515(15) 0.0265(6) Uani 1 1 d .
H18A H -0.3168 0.2535 0.4219 0.032 Uiso 1 1 calc R
H18B H -0.3932 0.2671 0.3369 0.032 Uiso 1 1 calc R
C19 C -0.5183(4) 0.4558(3) 0.39807(17) 0.0366(7) Uani 1 1 d .
H19A H -0.5774 0.508 0.3511 0.055 Uiso 1 1 calc R
H19B H -0.4669 0.5231 0.425 0.055 Uiso 1 1 calc R
H19C H -0.6201 0.4237 0.433 0.055 Uiso 1 1 calc R
C2 C 0.2475(3) 0.0433(3) -0.06142(14) 0.0199(6) Uani 1 1 d .
C8 C 0.2284(3) 0.1192(3) 0.01004(14) 0.0184(5) Uani 1 1 d .
C3 C 0.2021(4) 0.2746(3) 0.00739(14) 0.0195(6) Uani 1 1 d .
H3A H 0.2012 0.3292 -0.0416 0.023 Uiso 1 1 calc R
C4 C 0.1781(4) 0.3458(3) 0.07425(14) 0.0194(6) Uani 1 1 d .
C11 C 0.2388(4) -0.1925(3) 0.16315(14) 0.0207(6) Uani 1 1 d .
H11 H 0.0987 -0.184 0.1857 0.025 Uiso 1 1 calc R
C12 C 0.3867(4) -0.3411(3) 0.17701(15) 0.0239(6) Uani 1 1 d .
H12A H 0.4961 -0.3755 0.1356 0.029 Uiso 1 1 calc R
H12B H 0.3369 -0.4211 0.206 0.029 Uiso 1 1 calc R
C17 C 0.1871(4) 0.2664(3) 0.29140(14) 0.0216(6) Uani 1 1 d .
H17A H 0.2276 0.3262 0.3278 0.026 Uiso 1 1 calc R
H17B H 0.2975 0.1744 0.2833 0.026 Uiso 1 1 calc R
C16 C 0.0024(4) 0.2250(3) 0.32784(14) 0.0211(6) Uani 1 1 d .
H16A H -0.0347 0.1603 0.2931 0.025 Uiso 1 1 calc R
H16B H 0.03 0.1688 0.3785 0.025 Uiso 1 1 calc R
C20 C -0.0014(4) 0.5727(3) 0.47468(14) 0.0214(6) Uani 1 1 d .
C13 C 0.3891(4) -0.2104(3) 0.22129(15) 0.0232(6) Uani 1 1 d .
H13A H 0.3407 -0.2101 0.2775 0.028 Uiso 1 1 calc R
H13B H 0.4999 -0.1646 0.2071 0.028 Uiso 1 1 calc R
O5 O 0.0638(3) 0.66546(19) 0.50279(10) 0.0286(5) Uani 1 1 d .
O4 O -0.0693(3) 0.58444(19) 0.40891(10) 0.0257(4) Uani 1 1 d .
H3 H -0.137(4) 0.420(3) 0.3751(15) 0.024(7) Uiso 1 1 d .
H1 H 0.273(6) -0.036(4) -0.180(2) 0.073(12) 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_3
C9 N1 C7 119.3(2) .
C9 N1 C11 119.3(2) .
C7 N1 C11 120.80(19) .
C15 N3 C18 112.39(19) .
C15 N3 C16 110.78(18) .
C18 N3 C16 109.72(19) .
O2 C10 O1 121.1(2) .
O2 C10 C1 123.0(2) .
O1 C10 C1 115.9(2) .
C9 C1 C10 118.0(2) .
C9 C1 C2 119.9(2) .
C2 C1 C10 122.0(2) .
N1 C9 C1 124.4(2) .
C6 C7 N1 120.1(2) .
C6 C7 C8 120.7(2) .
C8 C7 N1 119.2(2) .
C5 C6 C7 121.6(2) .
C6 C5 N2 122.9(2) .
C6 C5 C4 116.1(2) .
N2 C5 C4 120.9(2) .
C5 N2 C14 120.1(2) .
C5 N2 C17 118.20(19) .
C17 N2 C14 109.19(18) .
N2 C14 C15 112.4(2) .
N3 C15 C14 111.6(2) .
N3 C18 C19 112.2(2) .
O3 C2 C1 122.7(2) .
O3 C2 C8 121.9(2) .
C1 C2 C8 115.4(2) .
C7 C8 C2 121.7(2) .
C7 C8 C3 117.9(2) .
C3 C8 C2 120.4(2) .
C4 C3 C8 120.3(2) .
F1 C4 C5 118.1(2) .
C3 C4 F1 118.5(2) .
C3 C4 C5 123.4(2) .
N1 C11 C12 117.8(2) .
N1 C11 C13 120.3(2) .
C12 C11 C13 60.07(16) .
C11 C12 C13 59.96(16) .
N2 C17 C16 112.4(2) .
N3 C16 C17 109.9(2) .
O5 C20 C20 116.8(3) 2_566
O5 C20 O4 126.6(2) .
O4 C20 C20 116.6(3) 2_566
C11 C13 C12 59.97(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C4 1.357(3) .
O2 C10 1.216(3) .
O1 C10 1.336(3) .
N1 C9 1.341(3) .
N1 C7 1.405(3) .
N1 C11 1.457(3) .
N3 C15 1.495(3) .
N3 C18 1.495(3) .
N3 C16 1.498(3) .
O3 C2 1.262(3) .
C10 C1 1.482(3) .
C1 C9 1.372(3) .
C1 C2 1.435(3) .
C7 C6 1.397(3) .
C7 C8 1.402(3) .
C6 C5 1.394(3) .
C5 N2 1.395(3) .
C5 C4 1.417(3) .
N2 C14 1.473(3) .
N2 C17 1.463(3) .
C14 C15 1.519(4) .
C18 C19 1.511(4) .
C2 C8 1.450(3) .
C8 C3 1.413(3) .
C3 C4 1.352(3) .
C11 C12 1.501(3) .
C11 C13 1.501(3) .
C12 C13 1.503(3) .
C17 C16 1.514(4) .
C20 C20 1.551(5) 2_566
C20 O5 1.245(3) .
C20 O4 1.263(3) .
