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#$Date: 2025-08-18 16:20:24 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301776 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/54/1515458.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1515458
loop_
_publ_author_name
'Scott, Lauren E.'
'Telpoukhovskaia, Maria'
'Rodríguez-Rodríguez, Cristina'
'Merkel, Michael'
'Bowen, Meryn L.'
'Page, Brent D. G.'
'Green, David E.'
'Storr, Tim'
'Thomas, Fancy'
'Allen, David D.'
'Lockman, Paul R.'
'Patrick, Brian O.'
'Adam, Michael J.'
'Orvig, Chris'
_publ_section_title
;
 N-Aryl-substituted 3-(β-D-glucopyranosyloxy)-2-methyl-4(1H)-pyridinones
 as agents for Alzheimer's therapy
;
_journal_issue                   4
_journal_name_full               'Chemical Science'
_journal_page_first              642
_journal_paper_doi               10.1039/c0sc00544d
_journal_volume                  2
_journal_year                    2011
_chemical_formula_sum            'C13 H10 N2 O2 S'
_chemical_formula_weight         258.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 93.837(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.3006(12)
_cell_length_b                   7.8737(10)
_cell_length_c                   13.7999(16)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.98
_cell_measurement_theta_min      2.96
_cell_volume                     1116.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0140
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15521
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0332
_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/[σ²(Fo²)+(0.0401P)²+0.7272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0882
_reflns_number_gt                2323
_reflns_number_total             2541
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0sc00544d.txt
_cod_data_source_block           co351
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1515458
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.74480(14) 0.00879(19) 0.43359(10) 0.0239(3) Uani 1 1 d .
H1A H 0.7113 -0.0544 0.3760 0.036 Uiso 1 1 calc R
H1B H 0.8396 -0.0034 0.4414 0.036 Uiso 1 1 calc R
H1C H 0.7223 0.1292 0.4257 0.036 Uiso 1 1 calc R
C2 C 0.68548(13) -0.05990(17) 0.52156(10) 0.0181(3) Uani 1 1 d .
C3 C 0.60851(13) -0.20204(17) 0.51882(10) 0.0182(3) Uani 1 1 d .
C4 C 0.54161(13) -0.26012(18) 0.60152(10) 0.0190(3) Uani 1 1 d .
C5 C 0.56664(14) -0.1624(2) 0.68799(11) 0.0239(3) Uani 1 1 d .
H5 H 0.5284 -0.1959 0.7458 0.029 Uiso 1 1 calc R
C6 C 0.64353(14) -0.0231(2) 0.68932(10) 0.0239(3) Uani 1 1 d .
H6 H 0.6564 0.0403 0.7477 0.029 Uiso 1 1 calc R
C7 C 0.78466(13) 0.17547(18) 0.61730(10) 0.0196(3) Uani 1 1 d .
C8 C 0.95547(13) 0.33947(18) 0.61329(10) 0.0195(3) Uani 1 1 d .
C9 C 1.08245(14) 0.38932(19) 0.59760(11) 0.0240(3) Uani 1 1 d .
H9 H 1.1428 0.3104 0.5743 0.029 Uiso 1 1 calc R
C10 C 1.11860(14) 0.5556(2) 0.61661(11) 0.0262(3) Uani 1 1 d .
H10 H 1.2044 0.5912 0.6053 0.031 Uiso 1 1 calc R
C11 C 1.03156(16) 0.6723(2) 0.65203(11) 0.0279(3) Uani 1 1 d .
H11 H 1.0594 0.7855 0.6648 0.033 Uiso 1 1 calc R
C12 C 0.90561(16) 0.62635(19) 0.66889(11) 0.0262(3) Uani 1 1 d .
H12 H 0.8464 0.7056 0.6934 0.031 Uiso 1 1 calc R
C13 C 0.86883(13) 0.45855(19) 0.64846(10) 0.0205(3) Uani 1 1 d .
N1 N 0.70337(11) 0.02896(15) 0.60883(8) 0.0200(3) Uani 1 1 d .
N2 N 0.90504(11) 0.17619(15) 0.59666(9) 0.0215(3) Uani 1 1 d .
O1 O 0.46596(10) -0.38571(13) 0.59501(8) 0.0247(2) Uani 1 1 d .
O2 O 0.58990(11) -0.28691(14) 0.43373(7) 0.0259(2) Uani 1 1 d .
S1 S 0.71808(3) 0.36428(5) 0.65775(3) 0.02483(12) Uani 1 1 d .
H2O H 0.560(2) -0.377(3) 0.4431(18) 0.054(7) Uiso 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 N1 118.44(12)
C3 C2 C1 122.66(12)
N1 C2 C1 118.81(12)
O2 C3 C2 118.36(12)
O2 C3 C4 118.76(12)
C2 C3 C4 122.80(12)
O1 C4 C5 123.99(13)
O1 C4 C3 121.17(13)
C5 C4 C3 114.82(12)
C6 C5 C4 121.39(13)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 N1 121.82(13)
C5 C6 H6 119.1
N1 C6 H6 119.1
N2 C7 N1 123.58(13)
N2 C7 S1 118.09(11)
N1 C7 S1 118.33(10)
C9 C8 N2 125.02(13)
C9 C8 C13 119.33(13)
N2 C8 C13 115.64(12)
C10 C9 C8 118.70(14)
C10 C9 H9 120.6
C8 C9 H9 120.6
C9 C10 C11 121.28(14)
C9 C10 H10 119.4
C11 C10 H10 119.4
C12 C11 C10 121.32(14)
C12 C11 H11 119.3
C10 C11 H11 119.3
C11 C12 C13 117.27(14)
C11 C12 H12 121.4
C13 C12 H12 121.4
C12 C13 C8 122.09(13)
C12 C13 S1 128.45(12)
C8 C13 S1 109.45(10)
C6 N1 C2 120.66(12)
C6 N1 C7 118.02(12)
C2 N1 C7 121.31(11)
C7 N2 C8 108.62(12)
C3 O2 H2O 109.7(18)
C13 S1 C7 88.17(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.4963(19)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.3706(19)
C2 N1 1.3944(17)
C3 O2 1.3536(17)
C3 C4 1.4462(19)
C4 O1 1.2585(17)
C4 C5 1.429(2)
C5 C6 1.352(2)
C5 H5 0.9500
C6 N1 1.3686(18)
C6 H6 0.9500
C7 N2 1.2907(18)
C7 N1 1.4256(17)
C7 S1 1.7445(14)
C8 C9 1.3964(19)
C8 N2 1.3998(18)
C8 C13 1.403(2)
C9 C10 1.382(2)
C9 H9 0.9500
C10 C11 1.395(2)
C10 H10 0.9500
C11 C12 1.381(2)
C11 H11 0.9500
C12 C13 1.398(2)
C12 H12 0.9500
C13 S1 1.7335(14)
O2 H2O 0.79(3)
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
N1 C2 C3 O2 179.17(12)
C1 C2 C3 O2 2.6(2)
N1 C2 C3 C4 2.2(2)
C1 C2 C3 C4 -174.31(13)
O2 C3 C4 O1 -0.9(2)
C2 C3 C4 O1 176.01(13)
O2 C3 C4 C5 -179.71(12)
C2 C3 C4 C5 -2.8(2)
O1 C4 C5 C6 -176.41(14)
C3 C4 C5 C6 2.3(2)
C4 C5 C6 N1 -1.5(2)
N2 C8 C9 C10 179.54(13)
C13 C8 C9 C10 -0.5(2)
C8 C9 C10 C11 0.9(2)
C9 C10 C11 C12 -0.4(2)
C10 C11 C12 C13 -0.4(2)
C11 C12 C13 C8 0.7(2)
C11 C12 C13 S1 -177.63(12)
C9 C8 C13 C12 -0.3(2)
N2 C8 C13 C12 179.67(13)
C9 C8 C13 S1 178.34(11)
N2 C8 C13 S1 -1.70(16)
C5 C6 N1 C2 0.8(2)
C5 C6 N1 C7 -178.87(14)
C3 C2 N1 C6 -1.1(2)
C1 C2 N1 C6 175.55(13)
C3 C2 N1 C7 178.50(12)
C1 C2 N1 C7 -4.83(19)
N2 C7 N1 C6 124.06(15)
S1 C7 N1 C6 -55.93(16)
N2 C7 N1 C2 -55.57(19)
S1 C7 N1 C2 124.44(12)
N1 C7 N2 C8 -179.85(12)
S1 C7 N2 C8 0.14(16)
C9 C8 N2 C7 -179.01(14)
C13 C8 N2 C7 1.03(17)
C12 C13 S1 C7 179.90(14)
C8 C13 S1 C7 1.39(11)
N2 C7 S1 C13 -0.94(12)
N1 C7 S1 C13 179.05(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 10400278
