Crystal structure of canagliflozin hemihydrate
Liu, Kai-Hang; Gu, Jian-Ming; Hu, Xiu-Rong; Tang, Gu-Ping; Acta Crystallographica Section E 72 (2016) 734–736; doi:10.1107/S2056989016006769

data_2241659
_publ_section_title
;
 Crystal structure of canagliflozin hemihydrate
;
_journal_coeditor_code           XU5886
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              734
_journal_page_last               736
_journal_paper_doi               10.1107/S2056989016006769
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          '2C24 H25 F O5 S, H2 O'
_chemical_formula_moiety         '2(C24 H25 F O5 S), H2 O'
_chemical_formula_sum            'C24 H26 F O5.5 S'
_chemical_formula_weight         453.51
_chemical_name_common            canagliflozin
_chemical_name_systematic
'(2<i>S</i>,3<i>R</i>,4<i>R</i>,5<i>S</i>,6<i>R</i>)-2-(3-{[5-(4-Fluorophenyl)thiophen-2-yl]methyl}-4-methylphenyl)-6-(hydroxymethyl)-3,4,5,6-tetrahydro-2<i>H</i>-pyran-3,4,5-triol hemihydrate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.4259(4)
_cell_length_b                   11.4264(7)
_cell_length_c                   45.706(2)
_cell_measurement_reflns_used    23292
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      3.0
_cell_volume                     4400.5(4)
_computing_cell_refinement
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_collection
;
PROCESS-AUTO (Rigaku, 2006)
;
_computing_data_reduction
;
CrystalStructure (Rigaku, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Putz,
2005)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1447
_diffrn_reflns_av_sigmaI/netI    0.1274
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       59
_diffrn_reflns_limit_l_min       -59
_diffrn_reflns_number            43211
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.00
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.9518
_exptl_absorpt_correction_T_min  0.9136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(ABSCOR; Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1912
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.291
_refine_ls_abs_structure_details
;
Flack (1983), 3246 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.13(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         9958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0800
_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^)+(0.0408P)^2^+2.8647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                5079
_reflns_number_total             9958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            xu5886sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        4400.4(4)
_cod_database_code               2241659
_cod_database_fobs_code          2241659