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_2020853
_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'
_chemical_formula_moiety         'C21 H25 Cl O5 S'
_chemical_formula_sum            'C21 H25 Cl O5 S'
_chemical_formula_weight         424.92
_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
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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                   5.3945(4)
_cell_length_b                   9.1577(5)
_cell_length_c                   43.475(4)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    253(2)
_cell_measurement_theta_max      67.3610
_cell_measurement_theta_min      4.0400
_cell_volume                     2147.7(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      253(2)
_diffrn_detector_area_resol_mean 10.3575
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_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  0.0653
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            12259
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.110
_diffrn_reflns_theta_min         4.067
_exptl_absorpt_coefficient_mu    2.726
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO, Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       prism
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.205
_refine_ls_abs_structure_details
;
 Flack x determined using 1021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.031(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         3849
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.2004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1082
_reflns_number_gt                3081
_reflns_number_total             3849
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fm3052sup1.cif
_cod_data_source_block           I
_cod_database_code               2020853
_cod_database_fobs_code          2020853
_shelx_estimated_absorpt_t_min   0.685
_shelx_estimated_absorpt_t_max   0.899
_shelx_hkl_checksum              67265
_shelx_res_checksum              8542
_shelxl_version_number           2014/6