#------------------------------------------------------------------------------
#$Date: 2023-06-29 18:43:18 +0300 (Thu, 29 Jun 2023) $
#$Revision: 284690 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/27/2022783.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022783
loop_
_publ_author_name
'Abu-Zaied, Mamdouh A.'
'Hebishy, Ali M. S.'
'Elgemeie, Galal H.'
'Salama, Hagar T.'
'Jones, Peter G.'
_publ_section_title
;
 Crystal structure of
 5-(β-D-glucopyranosylthio)-N-(4-methylphenyl)-1,3,4-thiadiazol-2-amine
;
_journal_coeditor_code           YZ2035
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023005248
_journal_volume                  79
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H19 N3 O5 S2'
_chemical_formula_sum            'C15 H19 N3 O5 S2'
_chemical_formula_weight         385.45
_chemical_name_common
5-(β-D-Glucopyranosylthio)-N-(4-methylphenyl)-1,3,4-thiadiazol-2-amine
_chemical_name_systematic
5-[(β-D-Glucopyranosyl)sulfanyl]-N-(4-methylphenyl)-1,3,4-thiadiazol-2-amine
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.4183(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.23840(6)
_cell_length_b                   7.43550(10)
_cell_length_c                   18.32032(17)
_cell_measurement_reflns_used    61296
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.4830
_cell_measurement_theta_min      2.4120
_cell_volume                     849.539(16)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2021)
;
_computing_molecular_graphics
;
XP (Siemens, 1994)
;
_computing_publication_material
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015a)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            70354
_diffrn_reflns_theta_full        77.000
_diffrn_reflns_theta_max         77.276
_diffrn_reflns_theta_min         2.412
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    3.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2021)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.206
_refine_ls_abs_structure_details
;
Flack x determined using 1554 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   -0.006(5)
_refine_ls_extinction_coef       0.0009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2018/3 (Sheldrick, 2015a)
;
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3520
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0191
_refine_ls_R_factor_gt           0.0190
_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/[σ²(Fo²)+(0.0289P)²+0.2573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0496
_refine_ls_wR_factor_ref         0.0497
_reflns_number_gt                3502
_reflns_number_total             3520
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            yz2035sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022783
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.744
_shelx_estimated_absorpt_t_max   0.940
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.68679(6) 0.56520(6) 0.74337(2) 0.01368(10) Uani d 1 . .
C C2 0.7401(3) 0.7619(2) 0.69652(9) 0.0141(4) Uani d 1 . .
N N3 0.6138(2) 0.8948(2) 0.71166(8) 0.0164(3) Uani d 1 . .
N N4 0.4594(2) 0.8505(2) 0.76262(8) 0.0164(3) Uani d 1 . .
C C5 0.4713(3) 0.6807(3) 0.78116(9) 0.0141(3) Uani d 1 . .
C C11 1.0267(2) 0.5674(3) 0.61331(9) 0.0129(3) Uani d 1 . .
H H11 0.908249 0.505970 0.585259 0.015 Uiso calc 1 . .
C C12 1.2263(3) 0.5825(3) 0.56692(9) 0.0125(3) Uani d 1 . .
H H12 1.336334 0.656908 0.593626 0.015 Uiso calc 1 . .
C C13 1.3196(3) 0.3958(3) 0.55237(9) 0.0132(3) Uani d 1 . .
H H13 1.225617 0.331025 0.516019 0.016 Uiso calc 1 . .
C C14 1.3421(3) 0.2844(3) 0.62159(9) 0.0129(3) Uani d 1 . .
H H14 1.457744 0.336867 0.653816 0.015 Uiso calc 1 . .
C C15 1.1297(3) 0.2862(3) 0.66200(9) 0.0135(3) Uani d 1 . .
H H15 1.014260 0.235018 0.629328 0.016 Uiso calc 1 . .
C C16 1.1351(3) 0.1833(3) 0.73351(10) 0.0159(3) Uani d 1 . .
H H16A 1.005890 0.214160 0.761185 0.019 Uiso calc 1 . .
H H16B 1.129897 0.052814 0.722861 0.019 Uiso calc 1 . .
O O1 1.07795(19) 0.47115(17) 0.67845(7) 0.0135(3) Uani d 1 . .
O O2 1.1689(2) 0.66863(19) 0.50027(7) 0.0153(3) Uani d 1 . .
H H02 1.264(4) 0.740(4) 0.4908(15) 0.038(8) Uiso d 1 . .
O O3 1.52906(19) 0.41758(19) 0.52349(7) 0.0168(3) Uani d 1 . .
H H03 1.522(4) 0.482(4) 0.4857(13) 0.029(7) Uiso d 1 . .
O O4 1.3989(2) 0.10451(18) 0.60228(7) 0.0162(3) Uani d 1 . .
H H04 1.471(4) 0.067(4) 0.6365(12) 0.030(7) Uiso d 1 . .
O O5 1.3225(2) 0.22073(19) 0.77822(7) 0.0178(3) Uani d 1 . .
H H05 1.382(4) 0.122(3) 0.7831(14) 0.032(8) Uiso d 1 . .
N N1 0.3417(2) 0.5861(2) 0.82558(8) 0.0156(3) Uani d 1 . .
H H01 0.353(4) 0.473(4) 0.8230(13) 0.020(6) Uiso d 1 . .
C C21 0.1567(3) 0.6454(3) 0.86130(9) 0.0154(3) Uani d 1 . .
C C22 0.0393(3) 0.5129(3) 0.89691(10) 0.0191(4) Uani d 1 . .
H H22 0.082328 0.390608 0.894194 0.023 Uiso calc 1 . .
C C23 -0.1396(3) 0.5595(3) 0.93618(10) 0.0221(4) Uani d 1 . .
H H23 -0.216466 0.468512 0.960842 0.027 Uiso calc 1 . .
C C24 -0.2085(3) 0.7375(3) 0.94008(11) 0.0220(4) Uani d 1 . .
C C25 -0.0925(3) 0.8667(3) 0.90351(11) 0.0230(4) Uani d 1 . .
H H25 -0.138366 0.988413 0.905038 0.028 Uiso calc 1 . .
C C26 0.0901(3) 0.8234(3) 0.86446(10) 0.0195(4) Uani d 1 . .
H H26 0.167780 0.914713 0.840330 0.023 Uiso calc 1 . .
S S2 0.94984(6) 0.79473(6) 0.63645(2) 0.01473(10) Uani d 1 . .
C C27 -0.4029(3) 0.7886(4) 0.98327(13) 0.0322(5) Uani d 1 . .
H H27A -0.533285 0.765916 0.953762 0.048 Uiso calc 1 . .
H H27B -0.395250 0.916469 0.996023 0.048 Uiso calc 1 . .
H H27C -0.406140 0.716487 1.028010 0.048 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 S1 C5 . . 86.59(9) y
N3 C2 S1 . . 114.31(13) y
N3 C2 S2 . . 119.74(14) y
S1 C2 S2 . . 125.88(10) y
C2 N3 N4 . . 113.29(16) y
C5 N4 N3 . . 111.44(15) y
N4 C5 N1 . . 128.67(17) y
N4 C5 S1 . . 114.15(14) y
N1 C5 S1 . . 117.17(15) y
O1 C11 C12 . . 109.56(13) ?
O1 C11 S2 . . 109.19(11) ?
C12 C11 S2 . . 106.59(13) ?
O1 C11 H11 . . 110.5 ?
C12 C11 H11 . . 110.5 ?
S2 C11 H11 . . 110.5 ?
O2 C12 C11 . . 108.70(13) ?
O2 C12 C13 . . 110.40(13) ?
C11 C12 C13 . . 110.38(15) ?
O2 C12 H12 . . 109.1 ?
C11 C12 H12 . . 109.1 ?
C13 C12 H12 . . 109.1 ?
O3 C13 C14 . . 107.70(13) ?
O3 C13 C12 . . 108.45(14) ?
C14 C13 C12 . . 112.14(14) ?
O3 C13 H13 . . 109.5 ?
C14 C13 H13 . . 109.5 ?
C12 C13 H13 . . 109.5 ?
O4 C14 C13 . . 108.79(13) ?
O4 C14 C15 . . 110.46(15) ?
C13 C14 C15 . . 109.59(13) ?
O4 C14 H14 . . 109.3 ?
C13 C14 H14 . . 109.3 ?
C15 C14 H14 . . 109.3 ?
O1 C15 C16 . . 107.46(13) ?
O1 C15 C14 . . 107.97(14) ?
C16 C15 C14 . . 114.29(14) ?
O1 C15 H15 . . 109.0 ?
C16 C15 H15 . . 109.0 ?
C14 C15 H15 . . 109.0 ?
O5 C16 C15 . . 113.27(15) ?
O5 C16 H16A . . 108.9 ?
C15 C16 H16A . . 108.9 ?
O5 C16 H16B . . 108.9 ?
C15 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
C11 O1 C15 . . 110.51(13) ?
C12 O2 H02 . . 108(2) ?
C13 O3 H03 . . 109.9(19) ?
C14 O4 H04 . . 106(2) ?
C16 O5 H05 . . 104(2) ?
C5 N1 C21 . . 128.45(18) y
C5 N1 H01 . . 115.6(16) ?
C21 N1 H01 . . 113.9(17) ?
C26 C21 C22 . . 119.40(17) ?
C26 C21 N1 . . 124.47(17) ?
C22 C21 N1 . . 116.11(17) ?
C23 C22 C21 . . 120.26(19) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
C22 C23 C24 . . 121.12(19) ?
C22 C23 H23 . . 119.4 ?
C24 C23 H23 . . 119.4 ?
C25 C24 C23 . . 117.89(17) ?
C25 C24 C27 . . 120.9(2) ?
C23 C24 C27 . . 121.2(2) ?
C24 C25 C26 . . 122.0(2) ?
C24 C25 H25 . . 119.0 ?
C26 C25 H25 . . 119.0 ?
C21 C26 C25 . . 119.31(18) ?
C21 C26 H26 . . 120.3 ?
C25 C26 H26 . . 120.3 ?
C2 S2 C11 . . 102.94(8) ?
C24 C27 H27A . . 109.5 ?
C24 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C24 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 . 1.7322(19) y
S1 C5 . 1.7525(18) y
C2 N3 . 1.298(2) y
C2 S2 . 1.7473(17) y
N3 N4 . 1.397(2) y
N4 C5 . 1.309(3) y
C5 N1 . 1.358(2) y
C11 O1 . 1.421(2) ?
C11 C12 . 1.529(2) ?
C11 S2 . 1.811(2) y
C11 H11 . 1.0000 ?
C12 O2 . 1.417(2) ?
C12 C13 . 1.531(3) ?
C12 H12 . 1.0000 ?
C13 O3 . 1.4311(19) ?
C13 C14 . 1.518(2) ?
C13 H13 . 1.0000 ?
C14 O4 . 1.431(2) ?
C14 C15 . 1.534(2) ?
C14 H14 . 1.0000 ?
C15 O1 . 1.446(2) ?
C15 C16 . 1.517(2) ?
C15 H15 . 1.0000 ?
C16 O5 . 1.438(2) ?
C16 H16A . 0.9900 ?
C16 H16B . 0.9900 ?
O2 H02 . 0.82(2) ?
O3 H03 . 0.84(2) ?
O4 H04 . 0.81(2) ?
O5 H05 . 0.83(2) ?
N1 C21 . 1.411(2) y
N1 H01 . 0.84(3) ?
C21 C26 . 1.389(3) ?
C21 C22 . 1.398(3) ?
C22 C23 . 1.387(3) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.394(3) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.386(3) ?
C24 C27 . 1.513(2) ?
C25 C26 . 1.397(2) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H02 O3 2_856 0.82(2) 1.87(2) 2.6846(19) 174(3) yes
O3 H03 O4 2_856 0.84(2) 1.93(2) 2.7375(18) 161(3) yes
O4 H04 N3 1_645 0.81(2) 2.06(2) 2.848(2) 162(3) yes
O5 H05 N4 1_645 0.83(2) 2.11(2) 2.899(2) 159(3) yes
O5 H05 N3 1_645 0.83(2) 2.60(2) 3.282(2) 141(2) yes
N1 H01 O5 1_455 0.84(3) 2.05(3) 2.853(2) 158(2) yes
C14 H14 S1 1_655 1.00 2.74 3.7044(18) 162.5 yes
C15 H15 O2 2_746 1.00 2.66 3.577(2) 153.3 ?
C11 H11 O3 1_455 1.00 2.68 3.652(2) 164.3 ?
C16 H16B S2 1_545 0.99 2.71 3.570(2) 145.0 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 S1 C2 N3 . . . . 2.54(14) ?
C5 S1 C2 S2 . . . . 179.52(13) ?
S1 C2 N3 N4 . . . . -0.4(2) ?
S2 C2 N3 N4 . . . . -177.57(12) ?
C2 N3 N4 C5 . . . . -3.0(2) ?
N3 N4 C5 N1 . . . . -175.82(17) ?
N3 N4 C5 S1 . . . . 4.95(19) ?
C2 S1 C5 N4 . . . . -4.30(14) ?
C2 S1 C5 N1 . . . . 176.37(14) ?
O1 C11 C12 O2 . . . . 176.33(14) ?
S2 C11 C12 O2 . . . . -65.64(15) ?
O1 C11 C12 C13 . . . . 55.11(18) ?
S2 C11 C12 C13 . . . . 173.14(11) ?
O2 C12 C13 O3 . . . . 72.56(16) ?
C11 C12 C13 O3 . . . . -167.24(13) ?
O2 C12 C13 C14 . . . . -168.64(13) ?
C11 C12 C13 C14 . . . . -48.44(18) ?
O3 C13 C14 O4 . . . . -69.37(17) ?
C12 C13 C14 O4 . . . . 171.39(13) ?
O3 C13 C14 C15 . . . . 169.77(14) ?
C12 C13 C14 C15 . . . . 50.53(19) ?
O4 C14 C15 O1 . . . . -178.61(13) ?
C13 C14 C15 O1 . . . . -58.76(17) ?
O4 C14 C15 C16 . . . . 61.89(19) ?
C13 C14 C15 C16 . . . . -178.26(16) ?
O1 C15 C16 O5 . . . . -74.18(17) ?
C14 C15 C16 O5 . . . . 45.6(2) ?
C12 C11 O1 C15 . . . . -66.50(18) ?
S2 C11 O1 C15 . . . . 177.11(10) y
C16 C15 O1 C11 . . . . -168.02(13) ?
C14 C15 O1 C11 . . . . 68.24(16) ?
N4 C5 N1 C21 . . . . 2.2(3) ?
S1 C5 N1 C21 . . . . -178.54(14) ?
C5 N1 C21 C26 . . . . -9.0(3) ?
C5 N1 C21 C22 . . . . 172.65(16) ?
C26 C21 C22 C23 . . . . -1.2(3) ?
N1 C21 C22 C23 . . . . 177.18(16) ?
C21 C22 C23 C24 . . . . 1.1(3) ?
C22 C23 C24 C25 . . . . -0.1(3) ?
C22 C23 C24 C27 . . . . -179.64(18) ?
C23 C24 C25 C26 . . . . -0.9(3) ?
C27 C24 C25 C26 . . . . 178.71(19) ?
C22 C21 C26 C25 . . . . 0.3(3) ?
N1 C21 C26 C25 . . . . -177.94(17) ?
C24 C25 C26 C21 . . . . 0.7(3) ?
N3 C2 S2 C11 . . . . -164.51(14) y
S1 C2 S2 C11 . . . . 18.65(13) y
O1 C11 S2 C2 . . . . -55.86(12) y
C12 C11 S2 C2 . . . . -174.12(11) y

_cod_database_fobs_code 2022783
