Hydrogen-bonded structures and interaction energies in two forms of the SGLT-2 inhibitor sotagliflozin
Gelbrich, Thomas; Adamer, Verena; Stefinovic, Marijan; Thaler, Andrea; Griesser, Ulrich J.; Acta Crystallographica Section C 73 (2017) –; doi:10.1107/S2053229617011603

data_2020854
_publ_section_title
;
 Hydrogen-bonded structures and interaction energies in two forms of the
 SGLT-2 inhibitor sotagliflozin
;
_journal_coeditor_code           FM3052
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229617011603
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C21 H25 Cl O5 S, H2 O'
_chemical_formula_moiety         'C21 H25 Cl O5 S, H2 O'
_chemical_formula_sum            'C21 H27 Cl O6 S'
_chemical_formula_weight         442.93
_chemical_name_systematic
;(2<i>S</i>,3<i>R</i>,4<i>R</i>,5<i>S</i>,6<i>R</i>)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2<i>H</i>-pyran-3,4,5-triol
monohydrate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.4659(3)
_cell_length_b                   9.8994(8)
_cell_length_c                   48.073(5)
_cell_measurement_reflns_used    2038
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      67.2100
_cell_measurement_theta_min      4.5480
_cell_volume                     2125.3(3)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
XP (Bruker, 1998), Mercury (Macrae <i>et al.</i>,
2006) and
TOPOS (Blatov, 2006)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku Xcalibur Ruby (Gemini ultra)'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            11848
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.586
_diffrn_reflns_theta_min         3.678
_exptl_absorpt_coefficient_mu    2.812
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56003
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       prism
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.707
_refine_diff_density_min         -0.394
_refine_ls_abs_structure_details
;
 Flack x determined using 1099 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.350
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         3737
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.349
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0730
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0183P)^2^+2.0927P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1490
_reflns_number_gt                3253
_reflns_number_total             3737
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fm3052sup1.cif
_cod_data_source_block           II
_cod_database_code               2020854
_cod_database_fobs_code          2020854
_shelx_estimated_absorpt_t_min   0.806
_shelx_estimated_absorpt_t_max   0.872
_shelx_hkl_checksum              71441
_shelx_res_checksum              99544
_shelxl_version_number           2014/6