#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/50/2235090.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_2235090
loop_
_publ_author_name
'Duan, Anna'
'Yang, Haikui'
'Zhao, Peiliang'
'You, Wenwei'
_publ_section_title
;
 3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy-5,5-dimethylfuran-2(5H)-one
;
_journal_coeditor_code           IM2376
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1854
_journal_paper_doi               10.1107/S1600536812022404
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C21 H19 N O3 S2'
_chemical_formula_moiety         'C21 H19 N O3 S2'
_chemical_formula_sum            'C21 H19 N O3 S2'
_chemical_formula_weight         397.49
_chemical_name_systematic
;
3-{2-[(1,3-Benzothiazol-2-yl)sulfanylmethyl]phenyl}-4-methoxy-
5,5-dimethylfuran-2(5H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                117.5670(10)
_cell_angle_beta                 100.3980(10)
_cell_angle_gamma                95.2570(10)
_cell_formula_units_Z            2
_cell_length_a                   10.4702(9)
_cell_length_b                   10.4851(9)
_cell_length_c                   10.5169(9)
_cell_measurement_reflns_used    2192
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.59
_cell_measurement_theta_min      2.26
_cell_volume                     986.15(15)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0395
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7206
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.291
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_correction_T_min  0.9441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.224
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0447
_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)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1092
_reflns_number_gt                2713
_reflns_number_total             3804
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            im2376.cif
_cod_data_source_block           I
_cod_database_code               2235090
_cod_database_fobs_code          2235090
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.3099(2) 1.1296(2) 0.3804(2) 0.0429(5) Uani d . 1 1
C C2 0.1915(2) 1.1787(3) 0.3934(3) 0.0585(6) Uani d . 1 1
H H2 0.1101 1.1139 0.3439 0.070 Uiso calc R 1 1
C C3 0.1987(3) 1.3256(3) 0.4814(3) 0.0749(8) Uani d . 1 1
H H3 0.1207 1.3609 0.4920 0.090 Uiso calc R 1 1
C C4 0.3186(3) 1.4226(3) 0.5548(3) 0.0720(8) Uani d . 1 1
H H4 0.3199 1.5220 0.6133 0.086 Uiso calc R 1 1
C C5 0.4367(2) 1.3757(2) 0.5435(3) 0.0548(6) Uani d . 1 1
H H5 0.5172 1.4418 0.5944 0.066 Uiso calc R 1 1
C C6 0.4325(2) 1.2275(2) 0.4545(2) 0.0401(5) Uani d . 1 1
C C7 0.5064(2) 1.0231(2) 0.3504(2) 0.0393(5) Uani d . 1 1
C C8 0.7722(2) 1.0145(2) 0.3745(2) 0.0471(5) Uani d . 1 1
H H8A 0.7754 1.0955 0.4713 0.057 Uiso calc R 1 1
H H8B 0.8379 0.9594 0.3878 0.057 Uiso calc R 1 1
C C9 0.80777(19) 1.0755(2) 0.2782(2) 0.0383(5) Uani d . 1 1
C C10 0.82367(19) 0.9825(2) 0.1364(2) 0.0388(5) Uani d . 1 1
C C11 0.8548(2) 1.0439(2) 0.0510(2) 0.0468(5) Uani d . 1 1
H H11 0.8650 0.9830 -0.0432 0.056 Uiso calc R 1 1
C C12 0.8711(2) 1.1929(3) 0.1022(3) 0.0532(6) Uani d . 1 1
H H12 0.8919 1.2318 0.0433 0.064 Uiso calc R 1 1
C C13 0.8561(2) 1.2839(2) 0.2417(3) 0.0547(6) Uani d . 1 1
H H13 0.8674 1.3847 0.2775 0.066 Uiso calc R 1 1
C C14 0.8244(2) 1.2252(2) 0.3280(2) 0.0486(6) Uani d . 1 1
H H14 0.8140 1.2873 0.4217 0.058 Uiso calc R 1 1
C C15 0.8151(2) 0.8231(2) 0.0802(2) 0.0406(5) Uani d . 1 1
C C16 0.7292(2) 0.7023(2) -0.0266(2) 0.0495(6) Uani d . 1 1
C C17 0.7745(2) 0.5641(3) -0.0455(3) 0.0630(7) Uani d . 1 1
C C18 0.9225(2) 0.7703(3) 0.1412(3) 0.0514(6) Uani d . 1 1
C C19 0.5531(2) 0.8016(3) -0.1034(3) 0.0575(6) Uani d . 1 1
H H19A 0.5432 0.8556 -0.0043 0.086 Uiso calc R 1 1
H H19B 0.4677 0.7665 -0.1725 0.086 Uiso calc R 1 1
H H19C 0.6086 0.8647 -0.1235 0.086 Uiso calc R 1 1
C C20 0.6809(3) 0.4717(3) -0.0114(4) 0.0940(10) Uani d . 1 1
H H20A 0.7197 0.3923 -0.0111 0.141 Uiso calc R 1 1
H H20B 0.5983 0.4328 -0.0856 0.141 Uiso calc R 1 1
H H20C 0.6657 0.5315 0.0841 0.141 Uiso calc R 1 1
C C21 0.8059(3) 0.4778(3) -0.1948(3) 0.0900(10) Uani d . 1 1
H H21A 0.8612 0.5429 -0.2127 0.135 Uiso calc R 1 1
H H21B 0.7250 0.4334 -0.2718 0.135 Uiso calc R 1 1
H H21C 0.8515 0.4026 -0.1941 0.135 Uiso calc R 1 1
N N1 0.54360(17) 1.16332(19) 0.43437(18) 0.0421(4) Uani d . 1 1
O O1 1.02066(17) 0.84009(18) 0.2398(2) 0.0706(5) Uani d . 1 1
O O2 0.89788(16) 0.62095(17) 0.06858(18) 0.0649(5) Uani d . 1 1
O O3 0.61278(16) 0.67939(17) -0.11829(18) 0.0677(5) Uani d . 1 1
S S1 0.33515(6) 0.95239(6) 0.28478(6) 0.04817(18) Uani d . 1 1
S S2 0.60881(6) 0.89569(6) 0.29888(6) 0.04876(19) Uani d . 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 C6 121.1(2)
C2 C1 S1 129.24(18)
C6 C1 S1 109.60(16)
C3 C2 C1 117.8(2)
C3 C2 H2 121.1
C1 C2 H2 121.1
C2 C3 C4 121.6(2)
C2 C3 H3 119.2
C4 C3 H3 119.2
C3 C4 C5 121.4(2)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C6 118.3(2)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 N1 124.9(2)
C5 C6 C1 119.8(2)
N1 C6 C1 115.26(18)
N1 C7 S2 126.65(17)
N1 C7 S1 116.90(16)
S2 C7 S1 116.43(12)
C9 C8 S2 113.56(14)
C9 C8 H8A 108.9
S2 C8 H8A 108.9
C9 C8 H8B 108.9
S2 C8 H8B 108.9
H8A C8 H8B 107.7
C14 C9 C10 118.79(19)
C14 C9 C8 120.27(18)
C10 C9 C8 120.93(18)
C11 C10 C9 118.73(19)
C11 C10 C15 119.70(18)
C9 C10 C15 121.48(18)
C12 C11 C10 121.7(2)
C12 C11 H11 119.2
C10 C11 H11 119.2
C11 C12 C13 119.5(2)
C11 C12 H12 120.3
C13 C12 H12 120.3
C14 C13 C12 119.9(2)
C14 C13 H13 120.1
C12 C13 H13 120.1
C13 C14 C9 121.5(2)
C13 C14 H14 119.3
C9 C14 H14 119.3
C16 C15 C18 105.53(19)
C16 C15 C10 134.4(2)
C18 C15 C10 120.01(19)
O3 C16 C15 133.6(2)
O3 C16 C17 114.12(19)
C15 C16 C17 112.3(2)
O2 C17 C16 102.18(18)
O2 C17 C20 107.9(2)
C16 C17 C20 112.3(2)
O2 C17 C21 107.9(2)
C16 C17 C21 112.4(2)
C20 C17 C21 113.3(2)
O1 C18 O2 120.9(2)
O1 C18 C15 129.0(2)
O2 C18 C15 110.17(19)
O3 C19 H19A 109.5
O3 C19 H19B 109.5
H19A C19 H19B 109.5
O3 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C17 C21 H21A 109.5
C17 C21 H21B 109.5
H21A C21 H21B 109.5
C17 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C7 N1 C6 109.71(18)
C18 O2 C17 109.83(17)
C16 O3 C19 119.67(17)
C1 S1 C7 88.52(10)
C7 S2 C8 101.71(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.391(3)
C1 C6 1.403(3)
C1 S1 1.729(2)
C2 C3 1.367(3)
C2 H2 0.9300
C3 C4 1.377(3)
C3 H3 0.9300
C4 C5 1.377(3)
C4 H4 0.9300
C5 C6 1.385(3)
C5 H5 0.9300
C6 N1 1.397(3)
C7 N1 1.289(2)
C7 S2 1.741(2)
C7 S1 1.754(2)
C8 C9 1.504(3)
C8 S2 1.820(2)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C14 1.387(3)
C9 C10 1.406(3)
C10 C11 1.390(3)
C10 C15 1.480(3)
C11 C12 1.378(3)
C11 H11 0.9300
C12 C13 1.379(3)
C12 H12 0.9300
C13 C14 1.378(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C16 1.336(3)
C15 C18 1.471(3)
C16 O3 1.334(3)
C16 C17 1.503(3)
C17 O2 1.450(3)
C17 C20 1.517(4)
C17 C21 1.524(4)
C18 O1 1.201(3)
C18 O2 1.360(3)
C19 O3 1.433(3)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
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
C2 H2 O1 1_455 0.93 2.56 3.302(3) 137.2
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
C6 C1 C2 C3 -0.3(3)
S1 C1 C2 C3 177.37(19)
C1 C2 C3 C4 0.2(4)
C2 C3 C4 C5 -0.4(4)
C3 C4 C5 C6 0.7(4)
C4 C5 C6 N1 -178.7(2)
C4 C5 C6 C1 -0.8(3)
C2 C1 C6 C5 0.6(3)
S1 C1 C6 C5 -177.46(16)
C2 C1 C6 N1 178.74(18)
S1 C1 C6 N1 0.6(2)
S2 C8 C9 C14 114.53(19)
S2 C8 C9 C10 -64.9(2)
C14 C9 C10 C11 -0.3(3)
C8 C9 C10 C11 179.14(18)
C14 C9 C10 C15 176.32(18)
C8 C9 C10 C15 -4.2(3)
C9 C10 C11 C12 0.4(3)
C15 C10 C11 C12 -176.34(19)
C10 C11 C12 C13 0.0(3)
C11 C12 C13 C14 -0.4(3)
C12 C13 C14 C9 0.4(3)
C10 C9 C14 C13 -0.1(3)
C8 C9 C14 C13 -179.52(19)
C11 C10 C15 C16 -71.7(3)
C9 C10 C15 C16 111.7(3)
C11 C10 C15 C18 104.6(2)
C9 C10 C15 C18 -72.1(3)
C18 C15 C16 O3 178.4(2)
C10 C15 C16 O3 -5.0(4)
C18 C15 C16 C17 -1.3(3)
C10 C15 C16 C17 175.3(2)
O3 C16 C17 O2 -178.22(19)
C15 C16 C17 O2 1.5(3)
O3 C16 C17 C20 -62.8(3)
C15 C16 C17 C20 117.0(3)
O3 C16 C17 C21 66.4(3)
C15 C16 C17 C21 -113.8(2)
C16 C15 C18 O1 -179.5(2)
C10 C15 C18 O1 3.3(4)
C16 C15 C18 O2 0.5(2)
C10 C15 C18 O2 -176.70(18)
S2 C7 N1 C6 -177.70(14)
S1 C7 N1 C6 0.6(2)
C5 C6 N1 C7 177.21(19)
C1 C6 N1 C7 -0.8(2)
O1 C18 O2 C17 -179.5(2)
C15 C18 O2 C17 0.5(3)
C16 C17 O2 C18 -1.1(3)
C20 C17 O2 C18 -119.7(2)
C21 C17 O2 C18 117.5(2)
C15 C16 O3 C19 -4.9(4)
C17 C16 O3 C19 174.8(2)
C2 C1 S1 C7 -178.2(2)
C6 C1 S1 C7 -0.26(14)
N1 C7 S1 C1 -0.19(15)
S2 C7 S1 C1 178.27(12)
N1 C7 S2 C8 -6.61(19)
S1 C7 S2 C8 175.11(10)
C9 C8 S2 C7 -80.97(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30657776
2 PubChem 139083837
