Mutual prodrug of cephazolin and benzydamin: 3-[(1-benzyl-1<i>H</i>-indazol-3-yl)oxy]-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1<i>H</i>-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate (benzydaminium cephazolinate)
Asghar, Amina; Iqbal, Mohammad S.; Tahir, M. Nawaz; Acta Crystallographica Section E 65 (2009) o3132–o3133; doi:10.1107/S1600536809047941

data_2224253
_publ_section_title
;Mutual prodrug of cephazolin and benzydamin:
 3-[(1-benzyl-1<i>H</i>-indazol-3-yl)oxy]-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium
 3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-[(1<i>H</i>-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylate
 (benzydaminium cephazolinate)
;
_journal_coeditor_code           HB5219
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3132
_journal_page_last               o3133
_journal_paper_doi               10.1107/S1600536809047941
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H24 N3 O +, C14 H13 N8 O4 S3 -'
_chemical_formula_moiety         'C19 H24 N3 O +, C14 H13 N8 O4 S3 -'
_chemical_formula_sum            'C33 H37 N11 O5 S3'
_chemical_formula_weight         763.92
_chemical_name_common
;
benzydaminium cephazolinate
;
_chemical_name_systematic
;
3-[(1-Benzyl-1<i>H</i>-indazol-3-yl)oxy]-<i>N</i>,<i>N</i>-\
dimethylpropan-1-aminium
3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-7-\
[(1<i>H</i>-tetrazol-1-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]octane-2-\
carboxylate
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90.587(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   44.409(3)
_cell_length_b                   7.1777(5)
_cell_length_c                   11.2683(8)
_cell_measurement_reflns_used    3824
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.59
_cell_volume                     3591.6(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 7.60
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       \w
_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  0.0882
_diffrn_reflns_av_sigmaI/netI    0.1081
_diffrn_reflns_limit_h_max       54
_diffrn_reflns_limit_h_min       -54
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.265
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'cut needle'
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.229
_refine_ls_abs_structure_details 'Flack (1983), 2918 Friedal Pairs'
_refine_ls_abs_structure_Flack   -0.07(7)
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         6750
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0504
_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/[\s^2^(Fo^2^)+(0.0342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                4092
_reflns_number_total             6750
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            hb5219.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2224253
_cod_database_fobs_code          2224253