#------------------------------------------------------------------------------
#$Date: 2018-11-10 05:39:32 +0200 (Sat, 10 Nov 2018) $
#$Revision: 211894 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/27/2242734.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_2242734
loop_
_publ_author_name
'Frampton, Christopher S.'
'Frampton, Eleanor S.'
'Thomson, Paul A.'
_publ_section_title
;
 Two polymorphic forms of the oxathiin systemic fungicide active carboxine
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1741
_journal_page_last               1745
_journal_paper_doi               10.1107/S2056989018015451
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C12 H13 N O2 S'
_chemical_formula_sum            'C12 H13 N O2 S'
_chemical_formula_weight         235.29
_chemical_melting_point          364.13
_chemical_name_common
;
Carboxine Form II
;
_chemical_name_systematic
;
6-methyl-N-phenyl-2,3-dihydro-1,4-oxathiine-5-carboxamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90
_cell_angle_beta                 94.711(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6424(2)
_cell_length_b                   11.4059(3)
_cell_length_c                   21.6672(5)
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.7770
_cell_measurement_theta_min      4.0850
_cell_volume                     2374.91(10)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008), Mercury (Macrae et al.,
2008)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXD2014/6 (Schneider & Sheldrick, 2002)
;
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 5.2921
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku SuperNova, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4644
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.473
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.304
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       Plate
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.445
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0402
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0700P)²+2.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2244
_reflns_number_total             2415
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb7783sup1.cif
_cod_data_source_block           b17007r
_cod_original_cell_volume        2374.92(9)
_cod_database_code               2242734
_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   0.537
_shelx_estimated_absorpt_t_max   0.876
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -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_occupancy
S S1 0.41282(5) 0.67311(4) 0.72445(2) 0.03174(16) Uani d 1
O O1 0.32397(12) 0.46505(10) 0.64353(6) 0.0322(3) Uani d 1
O O2 0.58438(12) 0.80835(10) 0.62859(5) 0.0252(3) Uani d 1
N N1 0.55181(13) 0.43217(11) 0.62844(6) 0.0208(3) Uani d 1
H H1A 0.635(2) 0.4633(18) 0.6321(9) 0.023(5) Uiso d 1
C C1 0.43269(18) 0.23962(14) 0.61678(8) 0.0269(3) Uani d 1
H H1 0.3512 0.2694 0.6330 0.032 Uiso calc 1
C C2 0.4391(2) 0.12309(15) 0.59833(9) 0.0333(4) Uani d 1
H H2 0.3604 0.0739 0.6012 0.040 Uiso calc 1
C C3 0.5581(2) 0.07730(15) 0.57582(8) 0.0338(4) Uani d 1
H H3 0.5612 -0.0025 0.5635 0.041 Uiso calc 1
C C4 0.6725(2) 0.14945(16) 0.57147(8) 0.0318(4) Uani d 1
H H4 0.7551 0.1185 0.5568 0.038 Uiso calc 1
C C5 0.66723(17) 0.26668(15) 0.58839(8) 0.0260(3) Uani d 1
H H5 0.7455 0.3159 0.5845 0.031 Uiso calc 1
C C6 0.54737(16) 0.31217(13) 0.61114(7) 0.0213(3) Uani d 1
C C7 0.44398(16) 0.50099(14) 0.64111(7) 0.0218(3) Uani d 1
C C8 0.48110(15) 0.62578(13) 0.65536(7) 0.0207(3) Uani d 1
C C9 0.4412(2) 0.82819(14) 0.71537(9) 0.0315(4) Uani d 1
H H9A 0.3670 0.8613 0.6862 0.038 Uiso calc 1
H H9B 0.4372 0.8680 0.7558 0.038 Uiso calc 1
C C10 0.58140(19) 0.84960(15) 0.69104(8) 0.0297(4) Uani d 1
H H10A 0.6022 0.9346 0.6925 0.036 Uiso calc 1
H H10B 0.6543 0.8089 0.7179 0.036 Uiso calc 1
C C11 0.54640(16) 0.69442(13) 0.61652(7) 0.0206(3) Uani d 1
C C12 0.57867(18) 0.66346(14) 0.55218(8) 0.0262(3) Uani d 1
H H12A 0.5424 0.7246 0.5234 0.039 Uiso calc 1
H H12B 0.5351 0.5883 0.5403 0.039 Uiso calc 1
H H12C 0.6797 0.6572 0.5506 0.039 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C8 S1 C9 97.85(8)
C11 O2 C10 117.73(13)
C7 N1 C6 127.45(13)
C7 N1 H1A 117.4(13)
C6 N1 H1A 115.1(13)
C2 C1 C6 119.17(16)
C2 C1 H1 120.4
C6 C1 H1 120.4
C3 C2 C1 121.30(17)
C3 C2 H2 119.3
C1 C2 H2 119.3
C2 C3 C4 119.13(16)
C2 C3 H3 120.4
C4 C3 H3 120.4
C3 C4 C5 120.52(17)
C3 C4 H4 119.7
C5 C4 H4 119.7
C4 C5 C6 120.08(16)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 119.78(15)
C5 C6 N1 116.41(14)
C1 C6 N1 123.80(14)
O1 C7 N1 123.86(15)
O1 C7 C8 121.19(14)
N1 C7 C8 114.90(13)
C11 C8 C7 122.85(14)
C11 C8 S1 125.35(12)
C7 C8 S1 111.49(11)
C10 C9 S1 110.17(12)
C10 C9 H9A 109.6
S1 C9 H9A 109.6
C10 C9 H9B 109.6
S1 C9 H9B 109.6
H9A C9 H9B 108.1
O2 C10 C9 111.33(14)
O2 C10 H10A 109.4
C9 C10 H10A 109.4
O2 C10 H10B 109.4
C9 C10 H10B 109.4
H10A C10 H10B 108.0
C8 C11 O2 124.41(14)
C8 C11 C12 126.19(14)
O2 C11 C12 109.22(13)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C8 1.7684(15)
S1 C9 1.8031(17)
O1 C7 1.2328(19)
O2 C11 1.3694(19)
O2 C10 1.435(2)
N1 C7 1.349(2)
N1 C6 1.4188(19)
N1 H1A 0.87(2)
C1 C2 1.391(2)
C1 C6 1.395(2)
C1 H1 0.9500
C2 C3 1.385(3)
C2 H2 0.9500
C3 C4 1.385(3)
C3 H3 0.9500
C4 C5 1.388(2)
C4 H4 0.9500
C5 C6 1.393(2)
C5 H5 0.9500
C7 C8 1.494(2)
C8 C11 1.343(2)
C9 C10 1.511(3)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.496(2)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
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 H1A O1 6_665 0.87(2) 2.00(2) 2.8683(18) 178.1(18)
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 1.4(3)
C1 C2 C3 C4 -0.2(3)
C2 C3 C4 C5 -1.2(3)
C3 C4 C5 C6 1.3(3)
C4 C5 C6 C1 -0.1(2)
C4 C5 C6 N1 178.84(14)
C2 C1 C6 C5 -1.3(2)
C2 C1 C6 N1 179.90(15)
C7 N1 C6 C5 167.39(15)
C7 N1 C6 C1 -13.7(3)
C6 N1 C7 O1 5.4(3)
C6 N1 C7 C8 -177.45(14)
O1 C7 C8 C11 -126.69(18)
N1 C7 C8 C11 56.1(2)
O1 C7 C8 S1 47.26(19)
N1 C7 C8 S1 -130.00(12)
C9 S1 C8 C11 6.79(16)
C9 S1 C8 C7 -166.98(12)
C8 S1 C9 C10 -41.24(14)
C11 O2 C10 C9 -53.62(19)
S1 C9 C10 O2 67.88(16)
C7 C8 C11 O2 -178.68(14)
S1 C8 C11 O2 8.2(2)
C7 C8 C11 C12 6.6(2)
S1 C8 C11 C12 -166.46(12)
C10 O2 C11 C8 13.7(2)
C10 O2 C11 C12 -170.79(13)

_cod_database_fobs_code 2242734
