#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:42:19 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246069 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/16/2311649.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2311649
loop_
_publ_author_name
'Xu, Yun'
'Jiang, Linglei'
'Mei, Xuefeng'
_publ_section_title
;
 Supramolecular structures and physicochemical properties of norfloxacin
 salts.
;
_journal_issue                   'Pt 4'
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_page_first              750
_journal_page_last               760
_journal_paper_doi               10.1107/S2052520614011718
_journal_volume                  70
_journal_year                    2014
_chemical_formula_sum            'C23 H26 F N3 O7'
_chemical_formula_weight         475.47
_chemical_name_common            'NF o-OH-benzoate'
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_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                91.100(3)
_cell_angle_beta                 97.543(3)
_cell_angle_gamma                109.906(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0237(4)
_cell_length_b                   9.9645(5)
_cell_length_c                   17.4655(9)
_cell_measurement_temperature    296(2)
_cell_volume                     1136.71(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'CCD area detector'
_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  0.0291
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17531
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.18
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9967
_exptl_absorpt_correction_T_min  0.9839
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             500.0
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.203
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                2989
_reflns_number_total             5221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            og5069sup1.cif
_cod_data_source_block           2013329_0m
_cod_original_cell_volume        1136.71(10)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2311649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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_symmetry_multiplicity
F F1 0.82208(17) -0.33285(9) 0.61457(6) 0.0581(3) Uani d . 1 1
O O2 0.54571(18) 0.03225(15) 0.27079(7) 0.0529(3) Uani d . 1 1
H H2 0.553(3) -0.051(2) 0.2947(12) 0.079 Uiso d . 1 1
O O1S 0.2611(3) 0.0897(2) 0.04954(10) 0.0715(4) Uani d . 1 1
O O1 0.6433(2) 0.26226(14) 0.30653(7) 0.0662(4) Uani d . 1 1
O O3 0.61812(17) -0.13846(12) 0.36964(6) 0.0482(3) Uani d . 1 1
O O3' 0.7482(3) 0.28716(17) 0.78613(8) 0.0790(5) Uani d . 1 1
H H1' 0.812(4) 0.249(3) 0.8283(16) 0.118 Uiso d . 1 1
O O2' 0.8187(2) 0.19293(15) 0.91645(8) 0.0699(4) Uani d . 1 1
O O1' 0.65917(19) 0.21929(14) 1.01326(7) 0.0595(4) Uani d . 1 1
N N1 0.78967(19) 0.19248(12) 0.53606(7) 0.0349(3) Uani d . 1 1
N N2 0.93994(19) -0.11350(13) 0.73272(7) 0.0383(3) Uani d . 1 1
N N3 1.0486(2) -0.15138(14) 0.89301(7) 0.0438(4) Uani d . 1 1
H H15 1.1361 -0.1707 0.9298 0.053 Uiso calc R 1 1
H H14 0.9486 -0.1374 0.9159 0.053 Uiso calc R 1 1
C C3 0.6252(2) 0.1420(2) 0.32344(10) 0.0450(4) Uani d . 1 1
C C2 0.6840(2) 0.10546(17) 0.40286(9) 0.0360(4) Uani d . 1 1
C C1 0.7373(2) 0.20978(16) 0.46120(9) 0.0373(4) Uani d . 1 1
H H1 0.7374 0.2999 0.4482 0.045 Uiso calc R 1 1
C C10 0.7977(2) 0.05996(15) 0.55761(8) 0.0312(3) Uani d . 1 1
C C9 0.8576(2) 0.03828(16) 0.63500(9) 0.0339(4) Uani d . 1 1
H H8 0.8927 0.1139 0.6723 0.041 Uiso calc R 1 1
C C8 0.8660(2) -0.09337(16) 0.65762(9) 0.0343(4) Uani d . 1 1
C C11 1.0267(3) 0.01119(17) 0.78827(9) 0.0446(4) Uani d . 1 1
H H11 0.9169 0.0355 0.8063 0.054 Uiso calc R 1 1
H H10 1.1085 0.0923 0.7631 0.054 Uiso calc R 1 1
C C12 1.1588(3) -0.01935(18) 0.85661(9) 0.0467(4) Uani d . 1 1
H H13 1.2795 -0.0292 0.8394 0.056 Uiso calc R 1 1
H H12 1.2037 0.0611 0.8949 0.056 Uiso calc R 1 1
C C4 0.6764(2) -0.03538(17) 0.42026(9) 0.0353(4) Uani d . 1 1
C C5 0.7397(2) -0.05309(16) 0.50056(9) 0.0328(4) Uani d . 1 1
C C6 0.7441(2) -0.18632(16) 0.52364(9) 0.0368(4) Uani d . 1 1
H H9 0.7029 -0.2638 0.4872 0.044 Uiso calc R 1 1
C C7 0.8070(2) -0.20340(16) 0.59774(9) 0.0377(4) Uani d . 1 1
C C14 0.8209(3) -0.23983(18) 0.77048(10) 0.0500(5) Uani d . 1 1
H H18 0.7614 -0.3211 0.7328 0.060 Uiso calc R 1 1
H H19 0.7104 -0.2208 0.7912 0.060 Uiso calc R 1 1
C C13 0.9586(3) -0.27426(18) 0.83510(10) 0.0525(5) Uani d . 1 1
H H16 0.8803 -0.3577 0.8596 0.063 Uiso calc R 1 1
H H17 1.0669 -0.2959 0.8142 0.063 Uiso calc R 1 1
C C15 0.8401(3) 0.31597(16) 0.59305(10) 0.0441(4) Uani d . 1 1
H H4 0.7944 0.2819 0.6414 0.053 Uiso calc R 1 1
H H3 0.7675 0.3787 0.5740 0.053 Uiso calc R 1 1
C C16 1.0657(3) 0.3989(2) 0.60746(12) 0.0631(6) Uani d . 1 1
H H7 1.1373 0.3387 0.6291 0.095 Uiso calc R 1 1
H H6 1.0920 0.4800 0.6430 0.095 Uiso calc R 1 1
H H5 1.1119 0.4312 0.5595 0.095 Uiso calc R 1 1
C C5' 0.3426(4) 0.4400(2) 0.87721(14) 0.0801(7) Uani d . 1 1
H H4' 0.2519 0.4762 0.8970 0.096 Uiso calc R 1 1
C C6' 0.4481(3) 0.3696(2) 0.92331(12) 0.0623(5) Uani d . 1 1
H H5' 0.4267 0.3576 0.9745 0.075 Uiso calc R 1 1
C C1' 0.5853(3) 0.31638(17) 0.89481(10) 0.0444(4) Uani d . 1 1
C C2' 0.6148(3) 0.33448(17) 0.81754(11) 0.0512(5) Uani d . 1 1
C C7' 0.6953(3) 0.23853(18) 0.94519(11) 0.0477(4) Uani d . 1 1
C C4' 0.3748(4) 0.4556(2) 0.80116(14) 0.0788(7) Uani d . 1 1
H H3' 0.3054 0.5035 0.7697 0.095 Uiso calc R 1 1
C C3' 0.5051(4) 0.4027(2) 0.77122(12) 0.0679(6) Uani d . 1 1
H H2' 0.5212 0.4121 0.7194 0.081 Uiso calc R 1 1
H H1A 0.376(4) 0.137(3) 0.0435(16) 0.108(11) Uiso d . 1 1
H H1B 0.243(4) -0.001(3) 0.0584(15) 0.114(10) Uiso d . 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O2 H2 108.0(13)
H1A O1S H1B 114(3)
C2' O3' H1' 104.9(16)
C1 N1 C10 119.23(13)
C1 N1 C15 118.55(12)
C10 N1 C15 122.21(12)
C8 N2 C11 118.27(12)
C8 N2 C14 118.60(12)
C11 N2 C14 110.54(13)
C13 N3 C12 111.16(13)
C13 N3 H15 109.4
C12 N3 H15 109.4
C13 N3 H14 109.4
C12 N3 H14 109.4
H15 N3 H14 108.0
O1 C3 O2 120.98(16)
O1 C3 C2 123.45(16)
O2 C3 C2 115.55(15)
C1 C2 C4 119.56(14)
C1 C2 C3 117.94(15)
C4 C2 C3 122.41(14)
N1 C1 C2 124.95(14)
N1 C1 H1 117.5
C2 C1 H1 117.5
N1 C10 C5 118.62(13)
N1 C10 C9 121.15(13)
C5 C10 C9 120.20(13)
C8 C9 C10 121.96(14)
C8 C9 H8 119.0
C10 C9 H8 119.0
N2 C8 C9 122.61(14)
N2 C8 C7 121.77(13)
C9 C8 C7 115.49(14)
N2 C11 C12 110.59(13)
N2 C11 H11 109.5
C12 C11 H11 109.5
N2 C11 H10 109.5
C12 C11 H10 109.5
H11 C11 H10 108.1
N3 C12 C11 112.33(13)
N3 C12 H13 109.1
C11 C12 H13 109.1
N3 C12 H12 109.1
C11 C12 H12 109.1
H13 C12 H12 107.9
O3 C4 C2 122.77(14)
O3 C4 C5 121.69(14)
C2 C4 C5 115.54(13)
C10 C5 C6 117.79(14)
C10 C5 C4 121.94(13)
C6 C5 C4 120.26(14)
C7 C6 C5 120.87(14)
C7 C6 H9 119.6
C5 C6 H9 119.6
C6 C7 F1 117.43(14)
C6 C7 C8 123.65(14)
F1 C7 C8 118.87(14)
N2 C14 C13 109.84(14)
N2 C14 H18 109.7
C13 C14 H18 109.7
N2 C14 H19 109.7
C13 C14 H19 109.7
H18 C14 H19 108.2
N3 C13 C14 109.97(14)
N3 C13 H16 109.7
C14 C13 H16 109.7
N3 C13 H17 109.7
C14 C13 H17 109.7
H16 C13 H17 108.2
N1 C15 C16 111.80(14)
N1 C15 H4 109.3
C16 C15 H4 109.3
N1 C15 H3 109.3
C16 C15 H3 109.3
H4 C15 H3 107.9
C15 C16 H7 109.5
C15 C16 H6 109.5
H7 C16 H6 109.5
C15 C16 H5 109.5
H7 C16 H5 109.5
H6 C16 H5 109.5
C4' C5' C6' 118.6(2)
C4' C5' H4' 120.7
C6' C5' H4' 120.7
C5' C6' C1' 121.4(2)
C5' C6' H5' 119.3
C1' C6' H5' 119.3
C6' C1' C2' 118.57(17)
C6' C1' C7' 120.57(17)
C2' C1' C7' 120.84(18)
O3' C2' C3' 118.51(19)
O3' C2' C1' 121.81(16)
C3' C2' C1' 119.7(2)
O1' C7' O2' 122.89(16)
O1' C7' C1' 119.16(17)
O2' C7' C1' 117.94(17)
C3' C4' C5' 121.5(2)
C3' C4' H3' 119.3
C5' C4' H3' 119.3
C4' C3' C2' 120.3(2)
C4' C3' H2' 119.8
C2' C3' H2' 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C7 1.3640(17)
O2 C3 1.328(2)
O2 H2 0.95(2)
O1S H1A 0.80(3)
O1S H1B 0.89(3)
O1 C3 1.208(2)
O3 C4 1.2601(17)
O3' C2' 1.352(2)
O3' H1' 0.97(3)
O2' C7' 1.258(2)
O1' C7' 1.253(2)
N1 C1 1.3418(18)
N1 C10 1.3974(18)
N1 C15 1.4812(19)
N2 C8 1.3903(18)
N2 C11 1.463(2)
N2 C14 1.476(2)
N3 C13 1.476(2)
N3 C12 1.484(2)
N3 H15 0.9000
N3 H14 0.9000
C3 C2 1.483(2)
C2 C1 1.361(2)
C2 C4 1.426(2)
C1 H1 0.9300
C10 C5 1.402(2)
C10 C9 1.405(2)
C9 C8 1.395(2)
C9 H8 0.9300
C8 C7 1.414(2)
C11 C12 1.515(2)
C11 H11 0.9700
C11 H10 0.9700
C12 H13 0.9700
C12 H12 0.9700
C4 C5 1.447(2)
C5 C6 1.404(2)
C6 C7 1.345(2)
C6 H9 0.9300
C14 C13 1.510(2)
C14 H18 0.9700
C14 H19 0.9700
C13 H16 0.9700
C13 H17 0.9700
C15 C16 1.500(3)
C15 H4 0.9700
C15 H3 0.9700
C16 H7 0.9600
C16 H6 0.9600
C16 H5 0.9600
C5' C4' 1.379(3)
C5' C6' 1.382(3)
C5' H4' 0.9300
C6' C1' 1.386(3)
C6' H5' 0.9300
C1' C2' 1.398(2)
C1' C7' 1.493(2)
C2' C3' 1.387(3)
C4' C3' 1.354(3)
C4' H3' 0.9300
C3' H2' 0.9300
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
O1 C3 C2 C1 8.3(2)
O2 C3 C2 C1 -170.36(14)
O1 C3 C2 C4 -174.96(16)
O2 C3 C2 C4 6.4(2)
C10 N1 C1 C2 2.0(2)
C15 N1 C1 C2 -178.85(15)
C4 C2 C1 N1 1.6(2)
C3 C2 C1 N1 178.50(14)
C1 N1 C10 C5 -3.4(2)
C15 N1 C10 C5 177.49(14)
C1 N1 C10 C9 178.11(13)
C15 N1 C10 C9 -1.0(2)
N1 C10 C9 C8 179.83(14)
C5 C10 C9 C8 1.4(2)
C11 N2 C8 C9 -4.9(2)
C14 N2 C8 C9 133.47(16)
C11 N2 C8 C7 170.78(15)
C14 N2 C8 C7 -50.9(2)
C10 C9 C8 N2 174.89(13)
C10 C9 C8 C7 -1.0(2)
C8 N2 C11 C12 -161.49(14)
C14 N2 C11 C12 57.07(18)
C13 N3 C12 C11 52.96(19)
N2 C11 C12 N3 -53.34(19)
C1 C2 C4 O3 176.24(14)
C3 C2 C4 O3 -0.5(2)
C1 C2 C4 C5 -3.6(2)
C3 C2 C4 C5 179.71(13)
N1 C10 C5 C6 -178.50(13)
C9 C10 C5 C6 0.0(2)
N1 C10 C5 C4 1.3(2)
C9 C10 C5 C4 179.79(13)
O3 C4 C5 C10 -177.68(14)
C2 C4 C5 C10 2.1(2)
O3 C4 C5 C6 2.1(2)
C2 C4 C5 C6 -178.06(14)
C10 C5 C6 C7 -1.7(2)
C4 C5 C6 C7 178.48(14)
C5 C6 C7 F1 -175.05(14)
C5 C6 C7 C8 2.2(2)
N2 C8 C7 C6 -176.70(15)
C9 C8 C7 C6 -0.8(2)
N2 C8 C7 F1 0.5(2)
C9 C8 C7 F1 176.40(14)
C8 N2 C14 C13 157.90(14)
C11 N2 C14 C13 -60.81(19)
C12 N3 C13 C14 -55.73(19)
N2 C14 C13 N3 59.7(2)
C1 N1 C15 C16 -93.40(17)
C10 N1 C15 C16 85.68(18)
C4' C5' C6' C1' 0.6(3)
C5' C6' C1' C2' -0.4(3)
C5' C6' C1' C7' -179.03(18)
C6' C1' C2' O3' 179.05(17)
C7' C1' C2' O3' -2.3(3)
C6' C1' C2' C3' -1.0(3)
C7' C1' C2' C3' 177.68(16)
C6' C1' C7' O1' 1.4(3)
C2' C1' C7' O1' -177.18(15)
C6' C1' C7' O2' -179.73(17)
C2' C1' C7' O2' 1.7(2)
C6' C5' C4' C3' 0.5(3)
C5' C4' C3' C2' -1.9(3)
O3' C2' C3' C4' -177.92(19)
C1' C2' C3' C4' 2.1(3)
