Crystal structure of 4,6-dimethyl-2-{[3,4,5-trihy-droxy-6-(hy-droxy-meth-yl)tetra-hydro-2<i>H</i>-pyran-2-yl]sulfan-yl}nicotino-nitrile.
Masoud, Doaa M.; Hammad, Sherif F.; Elgemeie, Galal H.; Jones, Peter G.; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1751–1754; doi:10.1107/S2056989017015213

data_2312023
_publ_section_title
;
 Crystal structure of
 4,6-dimethyl-2-{[3,4,5-trihy-droxy-6-(hy-droxy-meth-yl)tetra-hydro-2<i>H</i>-pyran-2-yl]sulfan-yl}nicotino-nitrile.
;
_journal_coeditor_code           QM2120
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1751
_journal_page_last               1754
_journal_paper_doi               10.1107/S2056989017015213
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C14 H18 N2 O5 S'
_chemical_formula_moiety         'C14 H18 N2 O5 S'
_chemical_formula_sum            'C14 H18 N2 O5 S'
_chemical_formula_weight         326.36
_chemical_name_systematic
;
4,6-Dimethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-\
2<i>H</i>-pyran-2-yl]sulfanyl}nicotinonitrile
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 98.7356(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.66978(18)
_cell_length_b                   8.72860(13)
_cell_length_c                   23.7524(4)
_cell_measurement_reflns_used    46975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9130
_cell_measurement_theta_min      2.6900
_cell_volume                     1571.69(5)
_computing_cell_refinement
;
<i>CrysAlis PRO</i> (Rigaku Oxford Diffraction, 2015)
;
_computing_data_collection
;
<i>CrysAlis PRO</i> (Rigaku Oxford Diffraction, 2015)
;
_computing_data_reduction
;
<i>CrysAlis PRO</i> (Rigaku Oxford Diffraction, 2015)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2017 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.1419
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur Eos'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            84844
_diffrn_reflns_theta_full        30.500
_diffrn_reflns_theta_max         31.193
_diffrn_reflns_theta_min         2.489
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(<i>CrysAlis PRO</i>; Rigaku Oxford Diffraction, 2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.167
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 2066 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4741
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0256
_refine_ls_R_factor_gt           0.0241
_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^)+(0.0354P)^2^+0.4674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0621
_refine_ls_wR_factor_ref         0.0631
_reflns_number_gt                4590
_reflns_number_total             4741
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            qm2120sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'I 2'
_cod_database_code               2312023
_cod_database_fobs_code          2312023
_shelx_estimated_absorpt_t_min   0.913
_shelx_estimated_absorpt_t_max   0.955
_shelx_hkl_checksum              25008
_shelx_res_checksum              4368