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#$Date: 2021-02-05 16:53:45 +0200 (Fri, 05 Feb 2021) $
#$Revision: 261801 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022298.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_2022298
loop_
_publ_author_name
'Shishkina, Svitlana V.'
'Konovalova, Irina S.'
'Kovalenko, Sergiy M.'
'Kravchenko, Dmitriy V.'
'Bunyatyan, Natalya D.'
_publ_section_title
;
 Polymorphism of methyl 4-amino-3-phenylisothiazole-5-carboxylate: an
 experimental and theoretical study
;
_journal_coeditor_code           VP3011
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              40
_journal_page_last               48
_journal_paper_doi               10.1107/S2053229620016356
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C11 H10 N2 O2 S'
_chemical_formula_moiety         'C11 H10 N2 O2 S'
_chemical_formula_sum            'C11 H10 N2 O2 S'
_chemical_formula_weight         234.27
_chemical_name_systematic
;
Methyl 4-amino-3-phenylisothiazole-5-carboxylate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.9210(9)
_cell_length_b                   7.2371(17)
_cell_length_c                   42.396(8)
_cell_measurement_reflns_used    1207
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.23
_cell_measurement_theta_min      4.08
_cell_volume                     2123.5(7)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2018)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.1827
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1048
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            13405
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.096
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.373
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       stick
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.322
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1868
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0630P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1460
_reflns_number_gt                1262
_reflns_number_total             1868
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vp3011sup1.cif
_cod_data_source_block           1b
_cod_depositor_comments
'Adding full bibliography for 2022297--2022298.cif.'
_cod_database_code               2022298
_cod_database_fobs_code          2022298
_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   0.944
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.42918(11) 0.59107(14) 0.57558(2) 0.0505(3) Uani d 1 . .
O O1 0.9859(3) 0.6044(3) 0.55881(6) 0.0570(7) Uani d 1 . .
O O2 0.7258(3) 0.6860(4) 0.53025(5) 0.0567(7) Uani d 1 . .
N N1 0.3778(4) 0.5226(4) 0.61153(6) 0.0466(7) Uani d 1 . .
N N2 0.8945(4) 0.4892(5) 0.62263(8) 0.0507(8) Uani d 1 . .
H H2NA 1.005(6) 0.504(6) 0.6095(11) 0.087(14) Uiso d 1 . .
H H2NB 0.906(5) 0.447(4) 0.6411(9) 0.050(11) Uiso d 1 . .
C C1 0.5377(4) 0.4890(4) 0.62771(8) 0.0383(8) Uani d 1 . .
C C2 0.7147(4) 0.5166(4) 0.61061(7) 0.0376(8) Uani d 1 . .
C C3 0.6725(4) 0.5760(4) 0.58047(7) 0.0395(8) Uani d 1 . .
C C4 0.8140(5) 0.6202(5) 0.55628(8) 0.0444(8) Uani d 1 . .
C C5 0.8505(6) 0.7393(5) 0.50457(9) 0.0676(12) Uani d 1 . .
H H5A 0.918208 0.632711 0.496880 0.101 Uiso calc 1 . .
H H5B 0.941971 0.829417 0.511872 0.101 Uiso calc 1 . .
H H5C 0.774296 0.791444 0.487871 0.101 Uiso calc 1 . .
C C6 0.5208(4) 0.4307(4) 0.66074(8) 0.0392(8) Uani d 1 . .
C C7 0.3810(5) 0.3026(4) 0.66978(9) 0.0487(9) Uani d 1 . .
H H7 0.297328 0.253813 0.654777 0.058 Uiso calc 1 . .
C C8 0.3661(6) 0.2480(5) 0.70069(9) 0.0529(9) Uani d 1 . .
H H8 0.271709 0.162904 0.706452 0.063 Uiso calc 1 . .
C C9 0.4882(6) 0.3172(5) 0.72311(9) 0.0575(10) Uani d 1 . .
H H9 0.478398 0.277382 0.743911 0.069 Uiso calc 1 . .
C C10 0.6267(5) 0.4466(5) 0.71482(9) 0.0514(9) Uani d 1 . .
H H10 0.708180 0.496064 0.730091 0.062 Uiso calc 1 . .
C C11 0.6431(5) 0.5016(4) 0.68392(8) 0.0447(8) Uani d 1 . .
H H11 0.737122 0.587405 0.678373 0.054 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 0.0033 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
N1 S1 C3 . . 94.70(14) ?
C4 O2 C5 . . 116.2(3) ?
C1 N1 S1 . . 110.8(2) ?
C2 N2 H2NA . . 120(3) ?
C2 N2 H2NB . . 119(2) ?
H2NA N2 H2NB . . 121(4) ?
N1 C1 C2 . . 115.2(3) ?
N1 C1 C6 . . 118.7(3) ?
C2 C1 C6 . . 126.1(3) ?
N2 C2 C3 . . 125.9(3) ?
N2 C2 C1 . . 124.8(3) ?
C3 C2 C1 . . 109.3(3) ?
C2 C3 C4 . . 125.4(3) ?
C2 C3 S1 . . 110.0(2) ?
C4 C3 S1 . . 124.6(2) ?
O1 C4 O2 . . 123.8(3) ?
O1 C4 C3 . . 125.7(3) ?
O2 C4 C3 . . 110.5(3) ?
O2 C5 H5A . . 109.5 ?
O2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
O2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
C7 C6 C11 . . 118.2(3) ?
C7 C6 C1 . . 120.6(3) ?
C11 C6 C1 . . 121.2(3) ?
C8 C7 C6 . . 120.4(3) ?
C8 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
C9 C8 C7 . . 120.8(3) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 119.9(4) ?
C8 C9 H9 . . 120.0 ?
C10 C9 H9 . . 120.0 ?
C11 C10 C9 . . 119.6(3) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C10 C11 C6 . . 121.0(3) ?
C10 C11 H11 . . 119.5 ?
C6 C11 H11 . . 119.5 ?
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 N1 . 1.642(3) ?
S1 C3 . 1.701(3) ?
O1 C4 . 1.200(4) ?
O2 C4 . 1.348(4) ?
O2 C5 . 1.442(4) ?
N1 C1 . 1.324(4) ?
N2 C2 . 1.360(4) ?
N2 H2NA . 0.95(5) ?
N2 H2NB . 0.85(4) ?
C1 C2 . 1.438(4) ?
C1 C6 . 1.467(5) ?
C2 C3 . 1.379(4) ?
C3 C4 . 1.453(4) ?
C5 H5A . 0.9600 ?
C5 H5B . 0.9600 ?
C5 H5C . 0.9600 ?
C6 C7 . 1.394(4) ?
C6 C11 . 1.395(5) ?
C7 C8 . 1.373(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.367(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.386(5) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.374(4) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
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
N2 H2NA O1 . 0.95(5) 2.27(5) 2.901(5) 123(3)
N2 H2NA N1 1_655 0.95(5) 2.58(4) 3.386(4) 142(4)
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
C3 S1 N1 C1 . . . . 0.4(3) ?
S1 N1 C1 C2 . . . . -0.8(4) ?
S1 N1 C1 C6 . . . . 178.5(2) ?
N1 C1 C2 N2 . . . . -179.6(3) ?
C6 C1 C2 N2 . . . . 1.2(5) ?
N1 C1 C2 C3 . . . . 0.8(4) ?
C6 C1 C2 C3 . . . . -178.4(3) ?
N2 C2 C3 C4 . . . . -0.2(5) ?
C1 C2 C3 C4 . . . . 179.4(3) ?
N2 C2 C3 S1 . . . . -180.0(3) ?
C1 C2 C3 S1 . . . . -0.4(3) ?
N1 S1 C3 C2 . . . . 0.0(2) ?
N1 S1 C3 C4 . . . . -179.8(3) ?
C5 O2 C4 O1 . . . . -0.2(5) ?
C5 O2 C4 C3 . . . . 178.6(3) ?
C2 C3 C4 O1 . . . . 3.0(6) ?
S1 C3 C4 O1 . . . . -177.2(3) ?
C2 C3 C4 O2 . . . . -175.8(3) ?
S1 C3 C4 O2 . . . . 4.0(4) ?
N1 C1 C6 C7 . . . . 42.1(4) ?
C2 C1 C6 C7 . . . . -138.8(3) ?
N1 C1 C6 C11 . . . . -137.7(3) ?
C2 C1 C6 C11 . . . . 41.4(5) ?
C11 C6 C7 C8 . . . . -0.3(5) ?
C1 C6 C7 C8 . . . . 179.8(3) ?
C6 C7 C8 C9 . . . . -0.3(5) ?
C7 C8 C9 C10 . . . . 1.2(6) ?
C8 C9 C10 C11 . . . . -1.4(5) ?
C9 C10 C11 C6 . . . . 0.8(5) ?
C7 C6 C11 C10 . . . . 0.1(5) ?
C1 C6 C11 C10 . . . . 180.0(3) ?
