#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/73/2227310.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_2227310
loop_
_publ_author_name
'Shen, Shi-De'
'Feng, Xiao-Dong'
'Yang, Wei-Hua'
'Yao, Chang-Sheng'
_publ_section_title
;
 5'-Amino-2-oxo-2',3'-dihydrospiro[indoline-3,7'-thieno[3,2-b]pyran]-6'-carbonitrile
 1',1'-dioxide
;
_journal_coeditor_code           CI5148
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2448
_journal_paper_doi               10.1107/S1600536810032861
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H11 N3 O4 S'
_chemical_formula_moiety         'C15 H11 N3 O4 S'
_chemical_formula_sum            'C15 H11 N3 O4 S'
_chemical_formula_weight         329.33
_chemical_name_systematic
;
5'-Amino-2-oxo-2',3'-dihydrospiro[indoline-3,7'-thieno[3,2-b]pyran]-6'-
carbonitrile 1',1'-dioxide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 112.611(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   30.669(4)
_cell_length_b                   8.1760(14)
_cell_length_c                   12.229(2)
_cell_measurement_reflns_used    6345
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      33.40
_cell_measurement_theta_min      1.40
_cell_volume                     2830.7(8)
_computing_cell_refinement       'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_collection       'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert (Rigaku/MSC, 2009)'
_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      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            19659
_diffrn_reflns_theta_full        30.06
_diffrn_reflns_theta_max         30.06
_diffrn_reflns_theta_min         1.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.254
_exptl_absorpt_correction_T_max  0.9509
_exptl_absorpt_correction_T_min  0.9391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear-SM Expert; Rigaku/MSC, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4149
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0595P)²+0.5864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                3670
_reflns_number_total             4149
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci5148.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2227310
_cod_database_fobs_code          2227310
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_disorder_assembly
_atom_site_disorder_group
S S1 0.147537(9) 0.29057(3) 0.24536(2) 0.01647(9) Uani d . 1 . .
O O1 0.02172(3) 0.46422(10) 0.16158(7) 0.01616(16) Uani d . 1 . .
O O2 0.16145(3) 0.24351(12) 0.15034(8) 0.0273(2) Uani d . 1 . .
O O3 0.18485(3) 0.33938(10) 0.35503(7) 0.01955(17) Uani d . 1 . .
O O4 0.10067(3) 0.52484(10) -0.05002(7) 0.02012(18) Uani d . 1 . .
N N1 -0.02109(3) 0.68754(13) 0.09053(9) 0.0183(2) Uani d . 1 . .
N N2 0.16403(3) 0.67827(13) 0.06897(9) 0.0202(2) Uani d . 1 . .
N N3 0.05132(3) 0.96181(13) 0.00106(9) 0.0214(2) Uani d . 1 . .
C C1 0.02156(4) 0.62030(13) 0.12026(9) 0.0145(2) Uani d . 1 . .
C C2 0.06085(4) 0.68905(13) 0.11213(9) 0.0145(2) Uani d . 1 . .
C C3 0.10896(3) 0.60632(13) 0.15197(9) 0.0142(2) Uani d . 1 . .
C C4 0.10317(4) 0.43896(13) 0.19455(9) 0.0143(2) Uani d . 1 . .
C C5 0.06325(4) 0.37984(13) 0.19645(9) 0.0145(2) Uani d . 1 . .
C C6 0.06143(4) 0.21074(13) 0.23920(10) 0.0180(2) Uani d . 1 . .
H H6A 0.0382 0.1442 0.1757 0.022 Uiso calc R 1 . .
H H6B 0.0520 0.2125 0.3081 0.022 Uiso calc R 1 . .
C C7 0.11110(4) 0.13877(14) 0.27463(11) 0.0209(2) Uani d . 1 . .
H H7A 0.1100 0.0386 0.2282 0.025 Uiso calc R 1 . .
H H7B 0.1241 0.1098 0.3598 0.025 Uiso calc R 1 . .
C C8 0.05546(4) 0.84058(13) 0.05249(9) 0.0159(2) Uani d . 1 . .
C C9 0.12351(4) 0.59395(14) 0.04311(9) 0.0164(2) Uani d . 1 . .
C C10 0.18025(4) 0.74686(15) 0.18382(10) 0.0191(2) Uani d . 1 . .
C C11 0.14933(4) 0.70594(13) 0.23842(10) 0.0160(2) Uani d . 1 . .
C C12 0.15829(4) 0.75477(14) 0.35300(10) 0.0192(2) Uani d . 1 . .
H H12 0.1377 0.7253 0.3911 0.023 Uiso calc R 1 . .
C C13 0.19871(4) 0.84902(15) 0.41138(11) 0.0246(3) Uani d . 1 . .
H H13 0.2057 0.8843 0.4903 0.029 Uiso calc R 1 . .
C C14 0.22859(4) 0.89130(17) 0.35519(12) 0.0290(3) Uani d . 1 . .
H H14 0.2556 0.9564 0.3964 0.035 Uiso calc R 1 . .
C C15 0.22021(4) 0.84121(17) 0.24027(12) 0.0278(3) Uani d . 1 . .
H H15 0.2409 0.8702 0.2022 0.033 Uiso calc R 1 . .
H H1 -0.0266(6) 0.792(2) 0.0714(15) 0.032(4) Uiso d . 1 . .
H H2 -0.0445(6) 0.623(2) 0.0855(14) 0.030(4) Uiso d . 1 . .
H H3 0.1762(6) 0.6867(19) 0.0186(15) 0.030(4) Uiso d . 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 S1 O3 . . 116.71(6) ?
O2 S1 C4 . . 109.33(5) ?
O3 S1 C4 . . 111.62(5) ?
O2 S1 C7 . . 112.17(6) ?
O3 S1 C7 . . 109.72(5) ?
C4 S1 C7 . . 95.25(5) ?
C5 O1 C1 . . 117.12(8) ?
C1 N1 H1 . . 122.4(11) ?
C1 N1 H2 . . 117.5(11) ?
H1 N1 H2 . . 119.9(15) ?
C9 N2 C10 . . 112.12(10) ?
C9 N2 H3 . . 120.1(11) ?
C10 N2 H3 . . 127.8(11) ?
N1 C1 C2 . . 127.58(10) ?
N1 C1 O1 . . 110.36(9) ?
C2 C1 O1 . . 122.06(9) ?
C1 C2 C8 . . 117.77(9) ?
C1 C2 C3 . . 124.51(10) ?
C8 C2 C3 . . 117.44(9) ?
C4 C3 C11 . . 114.92(9) ?
C4 C3 C2 . . 106.69(8) ?
C11 C3 C2 . . 114.50(9) ?
C4 C3 C9 . . 110.35(9) ?
C11 C3 C9 . . 101.79(8) ?
C2 C3 C9 . . 108.38(8) ?
C5 C4 C3 . . 124.95(9) ?
C5 C4 S1 . . 109.79(8) ?
C3 C4 S1 . . 125.24(8) ?
C4 C5 O1 . . 124.61(10) ?
C4 C5 C6 . . 120.35(10) ?
O1 C5 C6 . . 115.04(9) ?
C5 C6 C7 . . 106.80(9) ?
C5 C6 H6A . . 110.4 ?
C7 C6 H6A . . 110.4 ?
C5 C6 H6B . . 110.4 ?
C7 C6 H6B . . 110.4 ?
H6A C6 H6B . . 108.6 ?
C6 C7 S1 . . 107.79(8) ?
C6 C7 H7A . . 110.1 ?
S1 C7 H7A . . 110.1 ?
C6 C7 H7B . . 110.1 ?
S1 C7 H7B . . 110.1 ?
H7A C7 H7B . . 108.5 ?
N3 C8 C2 . . 177.90(12) ?
O4 C9 N2 . . 126.97(10) ?
O4 C9 C3 . . 125.10(10) ?
N2 C9 C3 . . 107.86(9) ?
C15 C10 C11 . . 121.93(12) ?
C15 C10 N2 . . 128.42(11) ?
C11 C10 N2 . . 109.66(10) ?
C12 C11 C10 . . 120.70(10) ?
C12 C11 C3 . . 130.77(10) ?
C10 C11 C3 . . 108.54(10) ?
C11 C12 C13 . . 117.97(11) ?
C11 C12 H12 . . 121.0 ?
C13 C12 H12 . . 121.0 ?
C14 C13 C12 . . 120.66(12) ?
C14 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
C13 C14 C15 . . 121.88(12) ?
C13 C14 H14 . . 119.1 ?
C15 C14 H14 . . 119.1 ?
C10 C15 C14 . . 116.85(12) ?
C10 C15 H15 . . 121.6 ?
C14 C15 H15 . . 121.6 ?
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 O2 . 1.4359(9) ?
S1 O3 . 1.4448(9) ?
S1 C4 . 1.7491(11) ?
S1 C7 . 1.7957(12) ?
O1 C5 . 1.3648(12) ?
O1 C1 . 1.3719(13) ?
O4 C9 . 1.2221(14) ?
N1 C1 . 1.3340(14) ?
N1 H1 . 0.887(17) ?
N1 H2 . 0.877(17) ?
N2 C9 . 1.3480(15) ?
N2 C10 . 1.4133(16) ?
N2 H3 . 0.838(18) ?
N3 C8 . 1.1543(15) ?
C1 C2 . 1.3673(15) ?
C2 C8 . 1.4148(15) ?
C2 C3 . 1.5228(14) ?
C3 C4 . 1.4987(14) ?
C3 C11 . 1.5190(15) ?
C3 C9 . 1.5617(15) ?
C4 C5 . 1.3248(14) ?
C5 C6 . 1.4867(15) ?
C6 C7 . 1.5319(16) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C10 C15 . 1.3869(16) ?
C10 C11 . 1.3942(16) ?
C11 C12 . 1.3792(16) ?
C12 C13 . 1.3998(16) ?
C12 H12 . 0.95 ?
C13 C14 . 1.3842(19) ?
C13 H13 . 0.95 ?
C14 C15 . 1.390(2) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
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
N1 H1 N3 5_575 0.89(2) 2.21(2) 3.0878(15) 170(2)
N1 H2 O4 5_565 0.88(2) 2.01(2) 2.8790(14) 172.0(10)
N2 H3 O3 6_565 0.84(2) 2.13(2) 2.9255(14) 159(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_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 O1 C1 N1 . . . . -179.52(9) ?
C5 O1 C1 C2 . . . . 0.99(15) ?
N1 C1 C2 C8 . . . . -8.53(18) ?
O1 C1 C2 C8 . . . . 170.86(9) ?
N1 C1 C2 C3 . . . . 177.78(10) ?
O1 C1 C2 C3 . . . . -2.82(17) ?
C1 C2 C3 C4 . . . . 2.39(14) ?
C8 C2 C3 C4 . . . . -171.31(9) ?
C1 C2 C3 C11 . . . . -125.94(11) ?
C8 C2 C3 C11 . . . . 60.36(13) ?
C1 C2 C3 C9 . . . . 121.23(11) ?
C8 C2 C3 C9 . . . . -52.48(12) ?
C11 C3 C4 C5 . . . . 127.60(11) ?
C2 C3 C4 C5 . . . . -0.48(15) ?
C9 C3 C4 C5 . . . . -118.03(11) ?
C11 C3 C4 S1 . . . . -54.22(13) ?
C2 C3 C4 S1 . . . . 177.70(7) ?
C9 C3 C4 S1 . . . . 60.16(12) ?
O2 S1 C4 C5 . . . . 114.52(9) ?
O3 S1 C4 C5 . . . . -114.83(8) ?
C7 S1 C4 C5 . . . . -1.19(9) ?
O2 S1 C4 C3 . . . . -63.89(11) ?
O3 S1 C4 C3 . . . . 66.76(10) ?
C7 S1 C4 C3 . . . . -179.61(10) ?
C3 C4 C5 O1 . . . . -1.14(18) ?
S1 C4 C5 O1 . . . . -179.56(8) ?
C3 C4 C5 C6 . . . . 179.18(10) ?
S1 C4 C5 C6 . . . . 0.76(13) ?
C1 O1 C5 C4 . . . . 0.96(15) ?
C1 O1 C5 C6 . . . . -179.33(9) ?
C4 C5 C6 C7 . . . . 0.21(14) ?
O1 C5 C6 C7 . . . . -179.51(9) ?
C5 C6 C7 S1 . . . . -1.03(11) ?
O2 S1 C7 C6 . . . . -112.07(8) ?
O3 S1 C7 C6 . . . . 116.50(8) ?
C4 S1 C7 C6 . . . . 1.28(9) ?
C10 N2 C9 O4 . . . . 178.17(11) ?
C10 N2 C9 C3 . . . . 0.86(12) ?
C4 C3 C9 O4 . . . . 58.53(13) ?
C11 C3 C9 O4 . . . . -179.02(10) ?
C2 C3 C9 O4 . . . . -57.96(14) ?
C4 C3 C9 N2 . . . . -124.10(10) ?
C11 C3 C9 N2 . . . . -1.65(11) ?
C2 C3 C9 N2 . . . . 119.41(10) ?
C9 N2 C10 C15 . . . . -179.69(12) ?
C9 N2 C10 C11 . . . . 0.40(13) ?
C15 C10 C11 C12 . . . . -1.83(17) ?
N2 C10 C11 C12 . . . . 178.09(10) ?
C15 C10 C11 C3 . . . . 178.57(11) ?
N2 C10 C11 C3 . . . . -1.51(12) ?
C4 C3 C11 C12 . . . . -58.40(15) ?
C2 C3 C11 C12 . . . . 65.64(15) ?
C9 C3 C11 C12 . . . . -177.67(11) ?
C4 C3 C11 C10 . . . . 121.14(10) ?
C2 C3 C11 C10 . . . . -114.81(10) ?
C9 C3 C11 C10 . . . . 1.88(11) ?
C10 C11 C12 C13 . . . . 1.27(16) ?
C3 C11 C12 C13 . . . . -179.23(11) ?
C11 C12 C13 C14 . . . . -0.03(17) ?
C12 C13 C14 C15 . . . . -0.73(19) ?
C11 C10 C15 C14 . . . . 1.04(18) ?
N2 C10 C15 C14 . . . . -178.86(12) ?
C13 C14 C15 C10 . . . . 0.22(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139079554
