#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239662.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_2239662
loop_
_publ_author_name
'Shishkina, Svitlana V.'
'Ukrainets, Igor V.'
'Petrushova, Lidiya A.'
_publ_section_title
;
 (R,S)-2'-Amino-6'-methyl-2,5',5'-trioxo-6'H-spiro[indoline-3,4'-pyrano[3,2-c][2,1]benzothiazine]-3'-carbonitrile
 dimethylformamide monosolvate
;
_journal_coeditor_code           KP2471
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o786
_journal_page_last               o787
_journal_paper_doi               10.1107/S1600536814013634
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C20 H14 N4 O4 S, C3 H7 N O'
_chemical_formula_moiety         'C20 H14 N4 O4 S, C3 H7 N O'
_chemical_formula_sum            'C23 H21 N5 O5 S'
_chemical_formula_weight         479.51
_chemical_melting_point_gt       437
_chemical_melting_point_lt       439
_chemical_name_systematic
;(R,S)-2'-Amino-6'-methyl-2,5',5'-trioxo-6'H-spiro[indoline-3,4'-pyrano[3,2-c][2,1]benzothiazine]-3'-carbonitrile
dimethylformamide monosolvate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.2493(12)
_cell_length_b                   9.6046(5)
_cell_length_c                   27.7664(17)
_cell_measurement_reflns_used    2361
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.6
_cell_measurement_theta_min      3.2
_cell_volume                     4600.1(5)
_computing_cell_refinement
;
CrysAlis RED (Agilent, 2011)
;
_computing_data_collection
;
CrysAlis CCD (Agilent, 2011)
;
_computing_data_reduction
;
CrysAlis RED (Agilent, 2011)
;
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Agilent Xcalibur"3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            30060
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.9963
_exptl_absorpt_correction_T_min  0.9463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Agilent, 2011)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.268
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         4049
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.993
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0717
_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)+(0.0901P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1943
_reflns_number_gt                2147
_reflns_number_total             4049
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            kp2471sup1.cf
_cod_data_source_block           I
_cod_database_code               2239662
_cod_database_fobs_code          2239662
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.37888(7) 0.59466(11) 0.64282(4) 0.0534(4) Uani d . 1 1
O O1 0.58546(17) 0.4943(3) 0.59913(12) 0.0611(9) Uani d . 1 1
O O2 0.41460(16) 0.4674(3) 0.51036(9) 0.0464(7) Uani d . 1 1
O O3 0.30029(19) 0.5566(3) 0.65291(13) 0.0712(10) Uani d . 1 1
O O4 0.4331(2) 0.5859(3) 0.68127(12) 0.0748(10) Uani d . 1 1
O O5 0.1982(3) 0.3611(7) 0.7857(2) 0.157(2) Uani d . 1 1
N N1 0.5617(3) 0.3404(4) 0.66047(15) 0.0579(11) Uani d . 1 1
H H1N 0.605(3) 0.330(5) 0.6722(19) 0.073(18) Uiso d . 1 1
N N2 0.3820(2) 0.7522(3) 0.62123(14) 0.0569(10) Uani d . 1 1
N N3 0.4424(2) 0.2711(5) 0.47288(15) 0.0554(11) Uani d . 1 1
H H3NB 0.457(2) 0.189(4) 0.4712(15) 0.048(14) Uiso d . 1 1
H H3NA 0.434(2) 0.322(4) 0.4479(17) 0.057(15) Uiso d . 1 1
N N4 0.5120(2) 0.0310(4) 0.56205(14) 0.0653(12) Uani d . 1 1
N N5 0.3135(3) 0.3806(7) 0.8231(3) 0.1135(19) Uani d . 1 1
C C1 0.5437(2) 0.4109(4) 0.62037(16) 0.0475(11) Uani d . 1 1
C C2 0.4597(2) 0.3692(4) 0.60525(15) 0.0414(10) Uani d . 1 1
C C3 0.4343(3) 0.2863(4) 0.64885(15) 0.0448(11) Uani d . 1 1
C C4 0.3633(3) 0.2320(4) 0.66055(17) 0.0527(12) Uani d . 1 1
H H4 0.3212 0.2404 0.6398 0.063 Uiso calc R 1 1
C C5 0.3562(3) 0.1631(4) 0.70495(19) 0.0661(14) Uani d . 1 1
H H5 0.3082 0.1289 0.7146 0.079 Uiso calc R 1 1
C C6 0.4193(4) 0.1461(5) 0.73416(17) 0.0686(14) Uani d . 1 1
H H6 0.4136 0.0968 0.7628 0.082 Uiso calc R 1 1
C C7 0.4917(3) 0.2001(5) 0.72248(17) 0.0669(14) Uani d . 1 1
H H7 0.5344 0.1891 0.7426 0.080 Uiso calc R 1 1
C C8 0.4966(3) 0.2713(4) 0.67924(16) 0.0498(11) Uani d . 1 1
C C9 0.4128(2) 0.4982(4) 0.59449(15) 0.0394(10) Uani d . 1 1
C C10 0.3533(2) 0.7780(4) 0.57434(18) 0.0504(11) Uani d . 1 1
C C11 0.3224(3) 0.9077(4) 0.5625(2) 0.0643(14) Uani d . 1 1
H H11 0.3168 0.9758 0.5861 0.077 Uiso calc R 1 1
C C12 0.3004(3) 0.9344(5) 0.5162(2) 0.0743(16) Uani d . 1 1
H H12 0.2806 1.0216 0.5084 0.089 Uiso calc R 1 1
C C13 0.3070(3) 0.8350(5) 0.4807(2) 0.0685(14) Uani d . 1 1
H H13 0.2911 0.8548 0.4495 0.082 Uiso calc R 1 1
C C14 0.3368(2) 0.7075(4) 0.49171(17) 0.0511(11) Uani d . 1 1
H H14 0.3412 0.6405 0.4677 0.061 Uiso calc R 1 1
C C15 0.3609(2) 0.6756(4) 0.53878(16) 0.0444(11) Uani d . 1 1
C C16 0.3960(2) 0.5445(4) 0.55022(15) 0.0394(10) Uani d . 1 1
C C17 0.4408(2) 0.3341(4) 0.51557(15) 0.0415(10) Uani d . 1 1
C C18 0.4615(2) 0.2827(4) 0.55921(15) 0.0404(10) Uani d . 1 1
C C19 0.4899(2) 0.1437(4) 0.56126(15) 0.0459(11) Uani d . 1 1
C C20 0.3838(3) 0.8663(4) 0.65669(18) 0.0827(18) Uani d . 1 1
H H20C 0.3317 0.8908 0.6655 0.124 Uiso calc R 1 1
H H20B 0.4091 0.9458 0.6429 0.124 Uiso calc R 1 1
H H20A 0.4116 0.8367 0.6848 0.124 Uiso calc R 1 1
C C21 0.2672(5) 0.3931(5) 0.7875(2) 0.133(3) Uani d R 1 1
H H21 0.2881 0.4311 0.7595 0.159 Uiso calc R 1 1
C C22 0.3923(5) 0.4117(12) 0.8231(5) 0.251(8) Uani d . 1 1
H H22A 0.4055 0.4587 0.7938 0.376 Uiso calc R 1 1
H H22B 0.4216 0.3270 0.8256 0.376 Uiso calc R 1 1
H H22C 0.4040 0.4707 0.8501 0.376 Uiso calc R 1 1
C C23 0.2835(7) 0.3142(14) 0.8647(5) 0.259(7) Uani d . 1 1
H H23A 0.2449 0.2474 0.8553 0.389 Uiso calc R 1 1
H H23B 0.2605 0.3825 0.8855 0.389 Uiso calc R 1 1
H H23C 0.3248 0.2676 0.8814 0.389 Uiso calc R 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
O4 S1 O3 117.4(2)
O4 S1 N2 108.0(2)
O3 S1 N2 109.9(2)
O4 S1 C9 109.15(19)
O3 S1 C9 109.5(2)
N2 S1 C9 101.58(19)
C17 O2 C16 119.9(3)
C1 N1 C8 111.3(4)
C10 N2 C20 119.5(4)
C10 N2 S1 119.3(3)
C20 N2 S1 116.5(3)
C21 N5 C22 126.3(9)
C21 N5 C23 116.4(7)
C22 N5 C23 116.9(10)
O1 C1 N1 126.4(4)
O1 C1 C2 125.6(4)
N1 C1 C2 108.0(4)
C9 C2 C3 115.7(3)
C9 C2 C18 107.0(3)
C3 C2 C18 112.9(3)
C9 C2 C1 110.0(3)
C3 C2 C1 100.9(3)
C18 C2 C1 110.3(3)
C4 C3 C8 120.9(4)
C4 C3 C2 130.5(4)
C8 C3 C2 108.6(4)
C3 C4 C5 117.7(5)
C6 C5 C4 120.5(5)
C5 C6 C7 122.1(5)
C8 C7 C6 116.2(5)
C3 C8 C7 122.5(5)
C3 C8 N1 110.3(4)
C7 C8 N1 127.2(5)
C16 C9 C2 124.8(4)
C16 C9 S1 117.4(3)
C2 C9 S1 117.8(3)
C11 C10 C15 119.9(5)
C11 C10 N2 120.5(4)
C15 C10 N2 119.5(4)
C12 C11 C10 119.7(5)
C11 C12 C13 121.4(4)
C14 C13 C12 119.7(5)
C13 C14 C15 121.0(4)
C10 C15 C14 118.3(4)
C10 C15 C16 120.1(4)
C14 C15 C16 121.5(4)
C9 C16 O2 120.8(3)
C9 C16 C15 126.0(4)
O2 C16 C15 113.3(3)
N3 C17 C18 128.6(4)
N3 C17 O2 109.8(4)
C18 C17 O2 121.5(4)
C17 C18 C19 117.9(4)
C17 C18 C2 123.0(3)
C19 C18 C2 119.0(3)
N4 C19 C18 178.5(5)
O5 C21 N5 127.8(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O4 1.422(3)
S1 O3 1.432(3)
S1 N2 1.628(4)
S1 C9 1.732(4)
O1 C1 1.228(5)
O2 C17 1.366(4)
O2 C16 1.370(5)
O5 C21 1.231(8)
N1 C1 1.339(6)
N1 C8 1.404(6)
N2 C10 1.415(6)
N2 C20 1.474(5)
N3 C17 1.331(5)
N4 C19 1.148(5)
N5 C21 1.277(8)
N5 C22 1.391(9)
N5 C23 1.417(11)
C1 C2 1.560(6)
C2 C9 1.510(5)
C2 C3 1.514(6)
C2 C18 1.525(6)
C3 C4 1.370(6)
C3 C8 1.374(6)
C4 C5 1.404(6)
C5 C6 1.367(7)
C6 C7 1.390(7)
C7 C8 1.384(6)
C9 C16 1.339(5)
C10 C11 1.394(6)
C10 C15 1.400(6)
C11 C12 1.365(7)
C12 C13 1.375(7)
C13 C14 1.363(6)
C14 C15 1.406(6)
C15 C16 1.432(5)
C17 C18 1.357(6)
C18 C19 1.423(6)
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
N1 H1N O5 6_657 0.82(5) 2.01(5) 2.797(7) 160(5) yes
N3 H3NA O1 5_666 0.86(5) 2.22(5) 3.051(6) 162(4) yes
N3 H3NB N4 5_656 0.83(4) 2.37(4) 3.159(6) 160(4) 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
O4 S1 N2 C10 160.2(3)
O3 S1 N2 C10 -70.5(4)
C9 S1 N2 C10 45.4(4)
O4 S1 N2 C20 -44.3(4)
O3 S1 N2 C20 85.0(4)
C9 S1 N2 C20 -159.1(3)
C8 N1 C1 O1 170.6(4)
C8 N1 C1 C2 -9.1(5)
O1 C1 C2 C9 -47.7(5)
N1 C1 C2 C9 132.0(4)
O1 C1 C2 C3 -170.4(4)
N1 C1 C2 C3 9.3(4)
O1 C1 C2 C18 70.0(5)
N1 C1 C2 C18 -110.3(4)
C9 C2 C3 C4 54.1(6)
C18 C2 C3 C4 -69.7(5)
C1 C2 C3 C4 172.7(4)
C9 C2 C3 C8 -124.9(4)
C18 C2 C3 C8 111.3(4)
C1 C2 C3 C8 -6.4(4)
C8 C3 C4 C5 1.2(6)
C2 C3 C4 C5 -177.7(4)
C3 C4 C5 C6 -2.9(7)
C4 C5 C6 C7 2.7(7)
C5 C6 C7 C8 -0.6(7)
C4 C3 C8 C7 0.8(6)
C2 C3 C8 C7 179.9(4)
C4 C3 C8 N1 -177.5(4)
C2 C3 C8 N1 1.6(5)
C6 C7 C8 C3 -1.1(7)
C6 C7 C8 N1 176.9(4)
C1 N1 C8 C3 5.0(5)
C1 N1 C8 C7 -173.2(4)
C3 C2 C9 C16 -144.0(4)
C18 C2 C9 C16 -17.2(5)
C1 C2 C9 C16 102.6(5)
C3 C2 C9 S1 36.8(4)
C18 C2 C9 S1 163.6(3)
C1 C2 C9 S1 -76.7(4)
O4 S1 C9 C16 -146.6(3)
O3 S1 C9 C16 83.5(3)
N2 S1 C9 C16 -32.7(4)
O4 S1 C9 C2 32.7(3)
O3 S1 C9 C2 -97.2(3)
N2 S1 C9 C2 146.6(3)
C20 N2 C10 C11 -3.9(6)
S1 N2 C10 C11 150.8(3)
C20 N2 C10 C15 171.6(4)
S1 N2 C10 C15 -33.6(5)
C15 C10 C11 C12 -0.5(7)
N2 C10 C11 C12 175.0(5)
C10 C11 C12 C13 0.9(8)
C11 C12 C13 C14 -0.7(8)
C12 C13 C14 C15 0.1(7)
C11 C10 C15 C14 -0.1(6)
N2 C10 C15 C14 -175.6(4)
C11 C10 C15 C16 177.1(4)
N2 C10 C15 C16 1.5(6)
C13 C14 C15 C10 0.3(7)
C13 C14 C15 C16 -176.8(4)
C2 C9 C16 O2 6.7(6)
S1 C9 C16 O2 -174.0(3)
C2 C9 C16 C15 -170.9(4)
S1 C9 C16 C15 8.4(6)
C17 O2 C16 C9 9.0(5)
C17 O2 C16 C15 -173.1(3)
C10 C15 C16 C9 11.0(6)
C14 C15 C16 C9 -171.9(4)
C10 C15 C16 O2 -166.7(4)
C14 C15 C16 O2 10.3(5)
C16 O2 C17 N3 169.2(4)
C16 O2 C17 C18 -11.4(6)
N3 C17 C18 C19 0.8(7)
O2 C17 C18 C19 -178.6(3)
N3 C17 C18 C2 177.5(4)
O2 C17 C18 C2 -1.9(6)
C9 C2 C18 C17 14.6(5)
C3 C2 C18 C17 143.0(4)
C1 C2 C18 C17 -105.0(4)
C9 C2 C18 C19 -168.8(3)
C3 C2 C18 C19 -40.3(5)
C1 C2 C18 C19 71.7(5)
C17 C18 C19 N4 -3E1(2)
C2 C18 C19 N4 16E1(2)
C22 N5 C21 O5 176.6(8)
C23 N5 C21 O5 4.2(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086733
