Multidrug salt forms of norfloxacin with non-steroidal anti-inflammatory drugs: solubility and membrane permeability studies
Bhattacharya, Biswajit; Mondal, Amit; Soni, Saundray Raj; Das, Susobhan; Bhunia, Surojit; Bal Raju, K.; Ghosh, Animesh; Malla Reddy, C.; CrystEngComm 20 (2018) 6420–; doi:10.1039/C8CE00900G

data_7231538
_publ_section_title
;
 Multidrug salt forms of norfloxacin with non-steroidal anti-inflammatory
 drugs: solubility and membrane permeability studies
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              6420
_journal_paper_doi               10.1039/C8CE00900G
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         'C16 H19 F N3 O3, C13 H6 F2 O3'
_chemical_formula_sum            'C29 H25 F3 N3 O6'
_chemical_formula_weight         568.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2018-02-14 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.316(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.9178(4)
_cell_length_b                   18.4663(10)
_cell_length_c                   20.0399(10)
_cell_measurement_reflns_used    6164
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      26.3170
_cell_measurement_theta_min      2.1850
_cell_volume                     2557.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -65.00 119.00   1.00   12.91    --   27.17   0.00-180.00  184
  2  \w     35.00 124.00   1.00   12.91    --   27.17 178.00 150.00   89
  3  \w    -20.00  83.00   1.00   12.91    --   27.17 -99.00 -60.00  103
  4  \w    -11.00  42.00   1.00   12.91    --   27.17  57.00 -60.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158414000
_diffrn_orient_matrix_UB_12      0.0372334000
_diffrn_orient_matrix_UB_13      0.0063836000
_diffrn_orient_matrix_UB_21      -0.0096556000
_diffrn_orient_matrix_UB_22      -0.0077981000
_diffrn_orient_matrix_UB_23      0.0343780000
_diffrn_orient_matrix_UB_31      0.1009929000
_diffrn_orient_matrix_UB_32      0.0051194000
_diffrn_orient_matrix_UB_33      0.0056641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15195
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.03
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1180
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+3.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1222
_reflns_number_gt                4481
_reflns_number_total             5143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce00900g2.cif
_cod_data_source_block           NOR_DIF
_cod_depositor_comments
'Adding full bibliography for 7231537--7231540.cif.'
_cod_database_code               7231538
_chemical_oxdiff_formula         'C H N O F'
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: F2B(0.75) F2A(0.25)
3.a Secondary CH2 refined with riding coordinates:
 N3(H3A,H3B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B),
 C15(H15A,H15B)
3.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C21(H21), C23(H23), C1(H1), C7(H7), C20(H20), C26(H26), C28(H28)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
3.d Idealised tetrahedral OH refined as rotating group:
 O6(H6), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.631