#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/88/4508827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_4508827
loop_
_publ_author_name
'Basavoju, Srinivas'
'Boström, Dan'
'Velaga, Sitaram P.'
_publ_section_title
;
 Pharmaceutical Cocrystal and Salts of Norfloxacin
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2699
_journal_paper_doi               10.1021/cg060327x
_journal_volume                  6
_journal_year                    2006
_chemical_formula_moiety         'C16 H19 F N3 O3, 0.5(C4 H4 O4), H2 O'
_chemical_formula_sum            'C18 H23 F N3 O6'
_chemical_formula_weight         396.39
_chemical_name_common            'norfloxacin (succinate)0.5 hydrate'
_chemical_name_systematic        'norfloxacin (succinate)0.5 hydrate'
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.690(2)
_cell_angle_beta                 93.262(2)
_cell_angle_gamma                110.885(2)
_cell_formula_units_Z            2
_cell_length_a                   6.8086(2)
_cell_length_b                   9.3743(3)
_cell_length_c                   15.5127(4)
_cell_measurement_reflns_used    5448
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.317
_cell_measurement_theta_min      3.134
_cell_volume                     919.75(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi and omega scans'
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5555
_diffrn_reflns_theta_full        30.36
_diffrn_reflns_theta_max         30.36
_diffrn_reflns_theta_min         3.21
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular needles'
_exptl_crystal_F_000             418.0
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5529
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0823
_refine_ls_R_factor_gt           0.0596
_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)+(0.0477P)²+0.3821P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1391
_reflns_number_gt                4268
_reflns_number_total             5555
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg060327xsup1.cif
_cod_data_source_block           norfloxacin(succinate)0.5hydrate
_cod_original_formula_sum        'C18 H23 F N3 O6 '
_cod_database_code               4508827
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
O6 O -0.0510(2) -0.17974(17) 0.12452(9) 0.0457(4) Uani 1 1 d .
C18 C 0.5861(3) 0.21168(18) -0.02968(10) 0.0262(3) Uani 1 1 d .
C17 C 0.5682(4) 0.0452(2) -0.03043(16) 0.0505(6) Uani 1 1 d .
H20 H 0.5169 -0.0041 -0.0884 0.061 Uiso 1 1 calc R
H21 H 0.7085 0.0432 -0.0184 0.061 Uiso 1 1 calc R
O4 O 0.42797(18) 0.24521(13) -0.01398(7) 0.0296(3) Uani 1 1 d .
O5 O 0.75921(18) 0.30698(13) -0.04738(7) 0.0303(3) Uani 1 1 d .
H19 H 0.364(3) 0.386(2) 0.0537(12) 0.036(5) Uiso 1 1 d .
H17 H 0.286(3) 0.520(2) 0.0691(13) 0.043(5) Uiso 1 1 d .
H18 H 0.323(4) -0.040(3) 0.6933(17) 0.082(9) Uiso 1 1 d .
H22 H -0.185(6) -0.188(4) 0.076(2) 0.130(13) Uiso 1 1 d .
H23 H 0.035(5) -0.239(4) 0.092(2) 0.102(10) Uiso 1 1 d .
F1 F 0.48440(15) 0.45075(9) 0.39839(6) 0.0287(2) Uani 1 1 d .
C5 C 0.2847(2) 0.07622(16) 0.47984(9) 0.0177(3) Uani 1 1 d .
O3 O 0.36984(17) 0.09095(13) 0.63133(7) 0.0270(3) Uani 1 1 d .
N1 N 0.07888(19) -0.17160(13) 0.40609(8) 0.0195(3) Uani 1 1 d .
C10 C 0.1827(2) -0.01413(16) 0.40286(9) 0.0176(3) Uani 1 1 d .
O1 O 0.0937(2) -0.37607(14) 0.63507(8) 0.0382(3) Uani 1 1 d .
C2 C 0.1785(2) -0.15324(17) 0.55773(10) 0.0220(3) Uani 1 1 d .
C4 C 0.2828(2) 0.00870(17) 0.56158(9) 0.0206(3) Uani 1 1 d .
C8 C 0.2937(2) 0.20887(16) 0.32094(9) 0.0188(3) Uani 1 1 d .
O2 O 0.26677(19) -0.14943(15) 0.70848(7) 0.0325(3) Uani 1 1 d .
C9 C 0.1887(2) 0.05309(16) 0.32410(9) 0.0189(3) Uani 1 1 d .
H3 H 0.1213 -0.0078 0.2736 0.023 Uiso 1 1 calc R
C6 C 0.3887(2) 0.23476(16) 0.47666(9) 0.0201(3) Uani 1 1 d .
H2 H 0.4559 0.2967 0.5269 0.024 Uiso 1 1 calc R
N3 N 0.3125(2) 0.43974(15) 0.09493(8) 0.0230(3) Uani 1 1 d .
C7 C 0.3905(2) 0.29669(16) 0.40022(9) 0.0203(3) Uani 1 1 d .
N2 N 0.29914(19) 0.28382(14) 0.24601(8) 0.0212(3) Uani 1 1 d .
C1 C 0.0827(2) -0.23525(17) 0.48082(10) 0.0222(3) Uani 1 1 d .
H1 H 0.0168 -0.3409 0.4804 0.027 Uiso 1 1 calc R
C11 C 0.5033(2) 0.37643(17) 0.21718(9) 0.0215(3) Uani 1 1 d .
H5 H 0.5540 0.3127 0.1796 0.026 Uiso 1 1 calc R
H4 H 0.6058 0.4188 0.2669 0.026 Uiso 1 1 calc R
C14 C 0.1457(2) 0.20843(16) 0.17212(9) 0.0216(3) Uani 1 1 d .
H11 H 0.0141 0.1428 0.1921 0.026 Uiso 1 1 calc R
H10 H 0.1991 0.1458 0.1350 0.026 Uiso 1 1 calc R
C15 C -0.0247(2) -0.27282(17) 0.32688(10) 0.0245(3) Uani 1 1 d .
H12 H -0.0936 -0.2211 0.2905 0.029 Uiso 1 1 calc R
H13 H -0.1319 -0.3653 0.3427 0.029 Uiso 1 1 calc R
C13 C 0.1101(2) 0.33215(17) 0.12259(10) 0.0232(3) Uani 1 1 d .
H8 H 0.0127 0.2851 0.0719 0.028 Uiso 1 1 calc R
H9 H 0.0469 0.3891 0.1590 0.028 Uiso 1 1 calc R
C3 C 0.1737(2) -0.2378(2) 0.63581(10) 0.0279(3) Uani 1 1 d .
C12 C 0.4786(2) 0.50469(17) 0.16886(9) 0.0232(3) Uani 1 1 d .
H6 H 0.4392 0.5731 0.2079 0.028 Uiso 1 1 calc R
H7 H 0.6117 0.5633 0.1471 0.028 Uiso 1 1 calc R
C16 C 0.1343(3) -0.31539(19) 0.27647(11) 0.0327(4) Uani 1 1 d .
H15 H 0.0632 -0.3810 0.2254 0.049 Uiso 1 1 calc R
H16 H 0.2009 -0.3680 0.3121 0.049 Uiso 1 1 calc R
H14 H 0.2392 -0.2240 0.2600 0.049 Uiso 1 1 calc R
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'
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 0.0060 '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
H22 O6 H23 105(2) .
O4 C18 O5 124.11(14) .
O4 C18 C17 118.84(15) .
O5 C18 C17 117.02(15) .
C17 C17 C18 116.1(2) 2_655
C17 C17 H20 108.3 2_655
C18 C17 H20 108.3 .
C17 C17 H21 108.3 2_655
C18 C17 H21 108.3 .
H20 C17 H21 107.4 .
C6 C5 C10 118.77(12) .
C6 C5 C4 119.99(13) .
C10 C5 C4 121.25(13) .
C1 N1 C10 120.22(12) .
C1 N1 C15 118.53(12) .
C10 N1 C15 121.12(11) .
N1 C10 C9 120.86(12) .
N1 C10 C5 118.74(12) .
C9 C10 C5 120.39(13) .
C1 C2 C4 120.30(13) .
C1 C2 C3 118.36(14) .
C4 C2 C3 121.33(14) .
O3 C4 C2 123.07(13) .
O3 C4 C5 121.14(13) .
C2 C4 C5 115.79(13) .
C9 C8 N2 123.74(13) .
C9 C8 C7 117.24(12) .
N2 C8 C7 118.92(12) .
C3 O2 H18 107.5(15) .
C8 C9 C10 120.71(13) .
C8 C9 H3 119.6 .
C10 C9 H3 119.6 .
C7 C6 C5 119.64(13) .
C7 C6 H2 120.2 .
C5 C6 H2 120.2 .
C13 N3 C12 112.49(11) .
C13 N3 H19 108.8(12) .
C12 N3 H19 108.1(11) .
C13 N3 H17 108.8(13) .
C12 N3 H17 109.5(12) .
H19 N3 H17 109.0(16) .
C6 C7 F1 119.20(13) .
C6 C7 C8 123.22(13) .
F1 C7 C8 117.56(12) .
C8 N2 C14 119.45(12) .
C8 N2 C11 119.34(12) .
C14 N2 C11 111.12(11) .
N1 C1 C2 123.62(13) .
N1 C1 H1 118.2 .
C2 C1 H1 118.2 .
N2 C11 C12 109.33(12) .
N2 C11 H5 109.8 .
C12 C11 H5 109.8 .
N2 C11 H4 109.8 .
C12 C11 H4 109.8 .
H5 C11 H4 108.3 .
N2 C14 C13 107.75(12) .
N2 C14 H11 110.2 .
C13 C14 H11 110.2 .
N2 C14 H10 110.2 .
C13 C14 H10 110.2 .
H11 C14 H10 108.5 .
N1 C15 C16 111.09(13) .
N1 C15 H12 109.4 .
C16 C15 H12 109.4 .
N1 C15 H13 109.4 .
C16 C15 H13 109.4 .
H12 C15 H13 108.0 .
N3 C13 C14 111.24(12) .
N3 C13 H8 109.4 .
C14 C13 H8 109.4 .
N3 C13 H9 109.4 .
C14 C13 H9 109.4 .
H8 C13 H9 108.0 .
O1 C3 O2 121.57(14) .
O1 C3 C2 123.73(16) .
O2 C3 C2 114.70(14) .
N3 C12 C11 109.83(12) .
N3 C12 H6 109.7 .
C11 C12 H6 109.7 .
N3 C12 H7 109.7 .
C11 C12 H7 109.7 .
H6 C12 H7 108.2 .
C15 C16 H15 109.5 .
C15 C16 H16 109.5 .
H15 C16 H16 109.5 .
C15 C16 H14 109.5 .
H15 C16 H14 109.5 .
H16 C16 H14 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O6 H22 1.13(4) .
O6 H23 1.07(3) .
C18 O4 1.2566(19) .
C18 O5 1.2570(19) .
C18 C17 1.521(2) .
C17 C17 1.454(4) 2_655
C17 H20 0.9700 .
C17 H21 0.9700 .
F1 C7 1.3581(16) .
C5 C6 1.406(2) .
C5 C10 1.4077(19) .
C5 C4 1.4520(19) .
O3 C4 1.2689(18) .
N1 C1 1.3407(18) .
N1 C10 1.3967(18) .
N1 C15 1.4771(19) .
C10 C9 1.406(2) .
O1 C3 1.213(2) .
C2 C1 1.369(2) .
C2 C4 1.424(2) .
C2 C3 1.485(2) .
C8 C9 1.384(2) .
C8 N2 1.3920(18) .
C8 C7 1.420(2) .
O2 C3 1.335(2) .
O2 H18 1.01(3) .
C9 H3 0.9300 .
C6 C7 1.352(2) .
C6 H2 0.9300 .
N3 C13 1.494(2) .
N3 C12 1.4956(19) .
N3 H19 0.94(2) .
N3 H17 0.94(2) .
N2 C14 1.4621(18) .
N2 C11 1.4652(18) .
C1 H1 0.9300 .
C11 C12 1.511(2) .
C11 H5 0.9700 .
C11 H4 0.9700 .
C14 C13 1.513(2) .
C14 H11 0.9700 .
C14 H10 0.9700 .
C15 C16 1.519(2) .
C15 H12 0.9700 .
C15 H13 0.9700 .
C13 H8 0.9700 .
C13 H9 0.9700 .
C12 H6 0.9700 .
C12 H7 0.9700 .
C16 H15 0.9600 .
C16 H16 0.9600 .
C16 H14 0.9600 .
