##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1566461'
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;\
2-(2,2-Difluoroethoxy)-N-(5,8-dimethoxy-1,2,4-triazolo[1,5-c]\
pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide
;
_chemical_name_common     penoxsulam
_chemical_formula_moiety     'C16 H14 F5 N5 O5 S'
_chemical_formula_sum     'C16 H14 F5 N5 O5 S'
_chemical_formula_iupac     'C16 H14 F5 N5 O5 S'
_chemical_formula_weight     483.38
_chemical_melting_point     ?
_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.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.1945(3)
_cell_length_b     8.3733(3)
_cell_length_c     28.3277(9)
_cell_angle_alpha     82.698(2)
_cell_angle_beta     84.183(2)
_cell_angle_gamma     81.814(2)
_cell_volume     1901.43(12)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9990
_cell_measurement_theta_min     2.47
_cell_measurement_theta_max     27.28
_cell_measurement_temperature     173(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.190
_exptl_crystal_size_min     0.110
_exptl_crystal_density_diffrn     1.689
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     984
_exptl_absorpt_coefficient_mu     0.261
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.903
_shelx_estimated_absorpt_T_max     0.972
_exptl_absorpt_correction_T_min     0.6456
_exptl_absorpt_correction_T_max     0.7457
_diffrn_ambient_temperature     173(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     24336
_diffrn_reflns_av_R_equivalents     0.0320
_diffrn_reflns_theta_min     1.455
_diffrn_reflns_theta_max     24.997
_diffrn_reflns_theta_full     24.997
_diffrn_measured_fraction_theta_max     0.984
_diffrn_measured_fraction_theta_full     0.984
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -32
_diffrn_reflns_limit_l_max     33
_refine_special_details     ?
_reflns_number_total     6571
_reflns_number_gt     5503
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0541
_refine_ls_R_factor_gt     0.0440
_refine_ls_wR_factor_gt     0.1014
_refine_ls_wR_factor_ref     0.1058
_refine_ls_goodness_of_fit_ref     1.045
_refine_ls_restrained_S_all     1.045
_refine_ls_number_reflns     6571
_refine_ls_number_parameters     581
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0438P)²+1.5689P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.469
_refine_diff_density_min     -0.517
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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'
    'F' 'F' 0.0171 0.0103
                         '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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2010)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010)
;
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 0.40491(7) 0.27322(7) 0.33986(2) 0.02327(15) Uani d 1 . .
    S S2 1.17808(7) 0.29094(7) 0.15763(2) 0.02404(15) Uani d 1 . .
    F F1 0.6784(2) -0.21313(19) 0.28932(6) 0.0473(4) Uani d 1 . .
    F F2 0.6798(2) -0.2261(2) 0.36604(6) 0.0526(5) Uani d 1 . .
    F F3 0.0164(2) 0.53003(19) 0.34514(6) 0.0477(4) Uani d 1 . .
    F F4 0.18482(19) 0.53143(16) 0.28142(5) 0.0326(3) Uani d 1 . .
    F F5 -0.0713(2) 0.51888(19) 0.27738(6) 0.0465(4) Uani d 1 . .
    F F6 0.6485(2) 0.5512(2) 0.21727(6) 0.0501(4) Uani d 1 . .
    F F7 0.6787(3) 0.5868(2) 0.13991(7) 0.0629(5) Uani d 1 . .
    F F8 1.4342(2) -0.0947(2) 0.15363(6) 0.0505(5) Uani d 1 . .
    F F9 1.39010(18) 0.03048(19) 0.21686(5) 0.0381(4) Uani d 1 . .
    F F10 1.3647(2) -0.22070(19) 0.22130(6) 0.0523(5) Uani d 1 . .
    O O1 0.4016(2) -0.06137(18) 0.33033(6) 0.0292(4) Uani d 1 . .
    O O2 0.3455(2) 0.42426(19) 0.35764(6) 0.0343(4) Uani d 1 . .
    O O3 0.5333(2) 0.2632(2) 0.30221(6) 0.0356(4) Uani d 1 . .
    O O4 0.3555(3) -0.3031(3) 0.52168(8) 0.0591(6) Uani d 1 . .
    O O5 0.0298(3) 0.3079(3) 0.51945(7) 0.0460(5) Uani d 1 . .
    O O6 0.8254(2) 0.2966(2) 0.17644(6) 0.0309(4) Uani d 1 . .
    O O7 1.1568(2) 0.3944(2) 0.19444(6) 0.0349(4) Uani d 1 . .
    O O8 1.3393(2) 0.2352(2) 0.13777(6) 0.0334(4) Uani d 1 . .
    O O9 0.7015(3) 0.3776(3) -0.02223(8) 0.0535(6) Uani d 1 . .
    O O10 1.3171(3) 0.0395(3) -0.02043(7) 0.0449(5) Uani d 1 . .
    N N1 0.4795(2) 0.1502(2) 0.38497(7) 0.0250(4) Uani d 1 . .
    H H1N 0.5842 0.1083 0.3822 0.030 Uiso calc 1 . .
    N N2 0.4113(3) -0.0440(2) 0.44874(8) 0.0315(5) Uani d 1 . .
    N N3 0.2718(3) 0.2139(2) 0.44832(7) 0.0293(5) Uani d 1 . .
    N N4 0.2201(3) 0.1158(3) 0.48799(7) 0.0360(5) Uani d 1 . .
    N N5 0.0657(4) 0.0425(4) 0.55905(8) 0.0537(7) Uani d 1 . .
    N N6 1.0775(3) 0.3946(2) 0.11402(7) 0.0273(5) Uani d 1 . .
    H H6N 1.0315 0.4945 0.1175 0.033 Uiso calc 1 . .
    N N7 0.9191(3) 0.3767(2) 0.05042(7) 0.0313(5) Uani d 1 . .
    N N8 1.1790(3) 0.2324(3) 0.05044(7) 0.0303(5) Uani d 1 . .
    N N9 1.1034(3) 0.2116(3) 0.01107(7) 0.0354(5) Uani d 1 . .
    N N10 1.0719(3) 0.1088(3) -0.05969(8) 0.0483(6) Uani d 1 . .
    C C1 0.4275(3) -0.2344(3) 0.33482(10) 0.0319(6) Uani d 1 . .
    H H1A 0.3768 -0.2749 0.3091 0.038 Uiso calc 1 . .
    H H1B 0.3776 -0.2797 0.3661 0.038 Uiso calc 1 . .
    C C2 0.6090(4) -0.2821(3) 0.33091(10) 0.0366(7) Uani d 1 . .
    H H2 0.6349 -0.4030 0.3329 0.044 Uiso calc 1 . .
    C C3 0.2487(3) 0.0195(3) 0.32428(8) 0.0226(5) Uani d 1 . .
    C C4 0.1131(3) -0.0560(3) 0.31745(9) 0.0283(6) Uani d 1 . .
    H H4 0.1223 -0.1710 0.3198 0.034 Uiso calc 1 . .
    C C5 -0.0334(3) 0.0372(3) 0.30731(9) 0.0319(6) Uani d 1 . .
    H H5 -0.1263 -0.0142 0.3032 0.038 Uiso calc 1 . .
    C C6 -0.0480(3) 0.2044(3) 0.30301(9) 0.0291(6) Uani d 1 . .
    H H6 -0.1488 0.2671 0.2944 0.035 Uiso calc 1 . .
    C C7 0.0837(3) 0.2816(3) 0.31124(8) 0.0219(5) Uani d 1 . .
    C C8 0.2322(3) 0.1891(3) 0.32403(7) 0.0188(5) Uani d 1 . .
    C C9 0.0556(3) 0.4652(3) 0.30368(9) 0.0303(6) Uani d 1 . .
    C C10 0.3842(3) 0.1093(3) 0.42737(8) 0.0264(5) Uani d 1 . .
    C C11 0.3046(3) -0.0355(3) 0.48755(9) 0.0303(6) Uani d 1 . .
    C C12 0.2670(4) -0.1556(4) 0.52547(11) 0.0451(8) Uani d 1 . .
    C C13 0.1508(4) -0.1123(4) 0.55917(10) 0.0472(8) Uani d 1 . .
    H H13 0.1246 -0.1919 0.5848 0.057 Uiso calc 1 . .
    C C14 0.1007(4) 0.1546(4) 0.52415(9) 0.0400(7) Uani d 1 . .
    C C15 0.3152(5) -0.4323(4) 0.55754(13) 0.0761(13) Uani d 1 . .
    H H15A 0.3362 -0.4064 0.5890 0.114 Uiso calc 1 . .
    H H15B 0.3837 -0.5338 0.5506 0.114 Uiso calc 1 . .
    H H15C 0.1981 -0.4448 0.5575 0.114 Uiso calc 1 . .
    C C16 -0.0932(4) 0.3529(4) 0.55773(11) 0.0618(10) Uani d 1 . .
    H H16A -0.1876 0.2927 0.5580 0.093 Uiso calc 1 . .
    H H16B -0.1309 0.4697 0.5526 0.093 Uiso calc 1 . .
    H H16C -0.0443 0.3266 0.5884 0.093 Uiso calc 1 . .
    C C17 0.6501(3) 0.3241(3) 0.17727(11) 0.0388(7) Uani d 1 . .
    H H17A 0.5996 0.2640 0.2062 0.047 Uiso calc 1 . .
    H H17B 0.6132 0.2872 0.1487 0.047 Uiso calc 1 . .
    C C18 0.6008(4) 0.5018(4) 0.17763(12) 0.0460(8) Uani d 1 . .
    H H18 0.4782 0.5284 0.1767 0.055 Uiso calc 1 . .
    C C19 0.8998(3) 0.1400(3) 0.17952(8) 0.0244(5) Uani d 1 . .
    C C20 0.8126(3) 0.0072(3) 0.18630(9) 0.0326(6) Uani d 1 . .
    H H20 0.6953 0.0231 0.1871 0.039 Uiso calc 1 . .
    C C21 0.8963(3) -0.1464(3) 0.19184(9) 0.0350(6) Uani d 1 . .
    H H21 0.8369 -0.2372 0.1948 0.042 Uiso calc 1 . .
    C C22 1.0651(3) -0.1711(3) 0.19321(9) 0.0321(6) Uani d 1 . .
    H H22 1.1208 -0.2783 0.1991 0.039 Uiso calc 1 . .
    C C23 1.1547(3) -0.0404(3) 0.18604(8) 0.0238(5) Uani d 1 . .
    C C24 1.0729(3) 0.1177(3) 0.17622(8) 0.0203(5) Uani d 1 . .
    C C25 1.3353(3) -0.0779(3) 0.19369(9) 0.0344(6) Uani d 1 . .
    C C26 1.0613(3) 0.3314(3) 0.07141(8) 0.0257(5) Uani d 1 . .
    C C27 0.9510(3) 0.2979(3) 0.01135(8) 0.0275(6) Uani d 1 . .
    C C28 0.8526(4) 0.2892(3) -0.02617(10) 0.0407(7) Uani d 1 . .
    C C29 0.9154(4) 0.1956(4) -0.05974(9) 0.0422(7) Uani d 1 . .
    H H29 0.8498 0.1880 -0.0850 0.051 Uiso calc 1 . .
    C C30 1.1653(4) 0.1154(3) -0.02503(9) 0.0369(7) Uani d 1 . .
    C C31 0.5908(5) 0.3640(5) -0.05730(12) 0.0651(10) Uani d 1 . .
    H H31A 0.6383 0.4036 -0.0891 0.098 Uiso calc 1 . .
    H H31B 0.4841 0.4291 -0.0501 0.098 Uiso calc 1 . .
    H H31C 0.5747 0.2500 -0.0567 0.098 Uiso calc 1 . .
    C C32 1.3861(4) -0.0568(4) -0.05853(11) 0.0574(9) Uani d 1 . .
    H H32A 1.3238 -0.1487 -0.0580 0.086 Uiso calc 1 . .
    H H32B 1.5023 -0.0976 -0.0540 0.086 Uiso calc 1 . .
    H H32C 1.3789 0.0106 -0.0894 0.086 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 O3 . 1.4217(18) ?
    S1 O2 . 1.4238(18) ?
    S1 N1 . 1.6466(19) ?
    S1 C8 . 1.787(2) ?
    S2 O7 . 1.4207(18) ?
    S2 O8 . 1.4210(18) ?
    S2 N6 . 1.640(2) ?
    S2 C24 . 1.788(2) ?
    F1 C2 . 1.353(3) ?
    F2 C2 . 1.364(3) ?
    F3 C9 . 1.346(3) ?
    F4 C9 . 1.330(3) ?
    F5 C9 . 1.333(3) ?
    F6 C18 . 1.355(3) ?
    F7 C18 . 1.361(4) ?
    F8 C25 . 1.336(3) ?
    F9 C25 . 1.335(3) ?
    F10 C25 . 1.348(3) ?
    O1 C3 . 1.353(3) ?
    O1 C1 . 1.425(3) ?
    O4 C12 . 1.351(4) ?
    O4 C15 . 1.438(4) ?
    O5 C14 . 1.328(4) ?
    O5 C16 . 1.452(3) ?
    O6 C19 . 1.361(3) ?
    O6 C17 . 1.420(3) ?
    O9 C28 . 1.351(4) ?
    O9 C31 . 1.436(4) ?
    O10 C30 . 1.324(4) ?
    O10 C32 . 1.450(3) ?
    N1 C10 . 1.397(3) ?
    N1 H1N . 0.8800 ?
    N2 C11 . 1.336(3) ?
    N2 C10 . 1.346(3) ?
    N3 C10 . 1.326(3) ?
    N3 N4 . 1.373(3) ?
    N4 C11 . 1.355(3) ?
    N4 C14 . 1.380(4) ?
    N5 C14 . 1.313(4) ?
    N5 C13 . 1.382(4) ?
    N6 C26 . 1.403(3) ?
    N6 H6N . 0.8800 ?
    N7 C27 . 1.344(3) ?
    N7 C26 . 1.346(3) ?
    N8 C26 . 1.323(3) ?
    N8 N9 . 1.370(3) ?
    N9 C27 . 1.350(3) ?
    N9 C30 . 1.393(3) ?
    N10 C30 . 1.316(4) ?
    N10 C29 . 1.381(4) ?
    C1 C2 . 1.481(4) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.395(3) ?
    C3 C8 . 1.406(3) ?
    C4 C5 . 1.371(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.379(4) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.388(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.401(3) ?
    C7 C9 . 1.513(3) ?
    C11 C12 . 1.417(4) ?
    C12 C13 . 1.324(5) ?
    C13 H13 . 0.9500 ?
    C15 H15A . 0.9800 ?
    C15 H15B . 0.9800 ?
    C15 H15C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
    C17 C18 . 1.487(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 H18 . 1.0000 ?
    C19 C20 . 1.389(3) ?
    C19 C24 . 1.399(3) ?
    C20 C21 . 1.367(4) ?
    C20 H20 . 0.9500 ?
    C21 C22 . 1.373(4) ?
    C21 H21 . 0.9500 ?
    C22 C23 . 1.386(3) ?
    C22 H22 . 0.9500 ?
    C23 C24 . 1.403(3) ?
    C23 C25 . 1.501(4) ?
    C27 C28 . 1.413(4) ?
    C28 C29 . 1.326(4) ?
    C29 H29 . 0.9500 ?
    C31 H31A . 0.9800 ?
    C31 H31B . 0.9800 ?
    C31 H31C . 0.9800 ?
    C32 H32A . 0.9800 ?
    C32 H32B . 0.9800 ?
    C32 H32C . 0.9800 ?
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
    O3 S1 O2 . . 120.60(11) ?
    O3 S1 N1 . . 104.84(11) ?
    O2 S1 N1 . . 106.54(10) ?
    O3 S1 C8 . . 109.19(10) ?
    O2 S1 C8 . . 108.35(11) ?
    N1 S1 C8 . . 106.43(10) ?
    O7 S2 O8 . . 120.38(11) ?
    O7 S2 N6 . . 104.97(11) ?
    O8 S2 N6 . . 107.16(11) ?
    O7 S2 C24 . . 109.88(10) ?
    O8 S2 C24 . . 107.92(11) ?
    N6 S2 C24 . . 105.54(10) ?
    C3 O1 C1 . . 120.10(19) ?
    C12 O4 C15 . . 116.5(3) ?
    C14 O5 C16 . . 115.5(2) ?
    C19 O6 C17 . . 117.77(19) ?
    C28 O9 C31 . . 116.7(3) ?
    C30 O10 C32 . . 115.5(2) ?
    C10 N1 S1 . . 123.11(17) ?
    C10 N1 H1N . . 118.4 ?
    S1 N1 H1N . . 118.4 ?
    C11 N2 C10 . . 100.9(2) ?
    C10 N3 N4 . . 100.3(2) ?
    C11 N4 N3 . . 109.7(2) ?
    C11 N4 C14 . . 121.8(2) ?
    N3 N4 C14 . . 128.4(2) ?
    C14 N5 C13 . . 119.3(3) ?
    C26 N6 S2 . . 123.03(17) ?
    C26 N6 H6N . . 118.5 ?
    S2 N6 H6N . . 118.5 ?
    C27 N7 C26 . . 100.8(2) ?
    C26 N8 N9 . . 100.1(2) ?
    C27 N9 N8 . . 110.4(2) ?
    C27 N9 C30 . . 121.9(2) ?
    N8 N9 C30 . . 127.7(2) ?
    C30 N10 C29 . . 120.1(3) ?
    O1 C1 C2 . . 106.3(2) ?
    O1 C1 H1A . . 110.5 ?
    C2 C1 H1A . . 110.5 ?
    O1 C1 H1B . . 110.5 ?
    C2 C1 H1B . . 110.5 ?
    H1A C1 H1B . . 108.7 ?
    F1 C2 F2 . . 105.6(2) ?
    F1 C2 C1 . . 110.6(2) ?
    F2 C2 C1 . . 110.8(2) ?
    F1 C2 H2 . . 109.9 ?
    F2 C2 H2 . . 109.9 ?
    C1 C2 H2 . . 109.9 ?
    O1 C3 C4 . . 123.6(2) ?
    O1 C3 C8 . . 116.1(2) ?
    C4 C3 C8 . . 120.3(2) ?
    C5 C4 C3 . . 119.5(2) ?
    C5 C4 H4 . . 120.3 ?
    C3 C4 H4 . . 120.3 ?
    C4 C5 C6 . . 121.0(2) ?
    C4 C5 H5 . . 119.5 ?
    C6 C5 H5 . . 119.5 ?
    C5 C6 C7 . . 120.4(2) ?
    C5 C6 H6 . . 119.8 ?
    C7 C6 H6 . . 119.8 ?
    C6 C7 C8 . . 119.8(2) ?
    C6 C7 C9 . . 115.7(2) ?
    C8 C7 C9 . . 124.5(2) ?
    C7 C8 C3 . . 118.7(2) ?
    C7 C8 S1 . . 124.01(17) ?
    C3 C8 S1 . . 117.28(18) ?
    F4 C9 F5 . . 106.3(2) ?
    F4 C9 F3 . . 107.5(2) ?
    F5 C9 F3 . . 105.6(2) ?
    F4 C9 C7 . . 113.7(2) ?
    F5 C9 C7 . . 111.2(2) ?
    F3 C9 C7 . . 112.0(2) ?
    N3 C10 N2 . . 118.3(2) ?
    N3 C10 N1 . . 123.7(2) ?
    N2 C10 N1 . . 118.0(2) ?
    N2 C11 N4 . . 110.8(2) ?
    N2 C11 C12 . . 130.9(3) ?
    N4 C11 C12 . . 118.2(3) ?
    C13 C12 O4 . . 128.3(3) ?
    C13 C12 C11 . . 117.6(3) ?
    O4 C12 C11 . . 114.1(3) ?
    C12 C13 N5 . . 123.4(3) ?
    C12 C13 H13 . . 118.3 ?
    N5 C13 H13 . . 118.3 ?
    N5 C14 O5 . . 125.9(3) ?
    N5 C14 N4 . . 119.6(3) ?
    O5 C14 N4 . . 114.5(2) ?
    O4 C15 H15A . . 109.5 ?
    O4 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O4 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O5 C16 H16A . . 109.5 ?
    O5 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    O5 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
    O6 C17 C18 . . 106.7(2) ?
    O6 C17 H17A . . 110.4 ?
    C18 C17 H17A . . 110.4 ?
    O6 C17 H17B . . 110.4 ?
    C18 C17 H17B . . 110.4 ?
    H17A C17 H17B . . 108.6 ?
    F6 C18 F7 . . 105.9(2) ?
    F6 C18 C17 . . 110.2(3) ?
    F7 C18 C17 . . 111.1(2) ?
    F6 C18 H18 . . 109.9 ?
    F7 C18 H18 . . 109.9 ?
    C17 C18 H18 . . 109.9 ?
    O6 C19 C20 . . 123.2(2) ?
    O6 C19 C24 . . 116.2(2) ?
    C20 C19 C24 . . 120.5(2) ?
    C21 C20 C19 . . 119.7(2) ?
    C21 C20 H20 . . 120.1 ?
    C19 C20 H20 . . 120.1 ?
    C20 C21 C22 . . 120.8(2) ?
    C20 C21 H21 . . 119.6 ?
    C22 C21 H21 . . 119.6 ?
    C21 C22 C23 . . 120.3(2) ?
    C21 C22 H22 . . 119.8 ?
    C23 C22 H22 . . 119.8 ?
    C22 C23 C24 . . 119.8(2) ?
    C22 C23 C25 . . 116.3(2) ?
    C24 C23 C25 . . 123.7(2) ?
    C19 C24 C23 . . 118.3(2) ?
    C19 C24 S2 . . 118.21(17) ?
    C23 C24 S2 . . 123.49(18) ?
    F9 C25 F8 . . 108.1(2) ?
    F9 C25 F10 . . 105.0(2) ?
    F8 C25 F10 . . 105.2(2) ?
    F9 C25 C23 . . 113.5(2) ?
    F8 C25 C23 . . 114.2(2) ?
    F10 C25 C23 . . 110.2(2) ?
    N8 C26 N7 . . 118.5(2) ?
    N8 C26 N6 . . 123.6(2) ?
    N7 C26 N6 . . 117.9(2) ?
    N7 C27 N9 . . 110.3(2) ?
    N7 C27 C28 . . 131.1(3) ?
    N9 C27 C28 . . 118.6(2) ?
    C29 C28 O9 . . 128.1(3) ?
    C29 C28 C27 . . 117.8(3) ?
    O9 C28 C27 . . 114.0(3) ?
    C28 C29 N10 . . 122.9(3) ?
    C28 C29 H29 . . 118.5 ?
    N10 C29 H29 . . 118.5 ?
    N10 C30 O10 . . 126.7(3) ?
    N10 C30 N9 . . 118.7(3) ?
    O10 C30 N9 . . 114.6(2) ?
    O9 C31 H31A . . 109.5 ?
    O9 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    O9 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    O10 C32 H32A . . 109.5 ?
    O10 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    O10 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
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
    O3 S1 N1 C10 . . . . -171.86(18) ?
    O2 S1 N1 C10 . . . . 59.2(2) ?
    C8 S1 N1 C10 . . . . -56.2(2) ?
    C10 N3 N4 C11 . . . . 0.3(2) ?
    C10 N3 N4 C14 . . . . -179.1(2) ?
    O7 S2 N6 C26 . . . . -176.81(19) ?
    O8 S2 N6 C26 . . . . 54.1(2) ?
    C24 S2 N6 C26 . . . . -60.7(2) ?
    C26 N8 N9 C27 . . . . 0.3(2) ?
    C26 N8 N9 C30 . . . . -178.6(2) ?
    C3 O1 C1 C2 . . . . 168.7(2) ?
    O1 C1 C2 F1 . . . . -56.8(3) ?
    O1 C1 C2 F2 . . . . 59.8(3) ?
    C1 O1 C3 C4 . . . . -6.4(3) ?
    C1 O1 C3 C8 . . . . 175.1(2) ?
    O1 C3 C4 C5 . . . . -174.1(2) ?
    C8 C3 C4 C5 . . . . 4.3(3) ?
    C3 C4 C5 C6 . . . . 1.0(4) ?
    C4 C5 C6 C7 . . . . -3.2(4) ?
    C5 C6 C7 C8 . . . . 0.0(3) ?
    C5 C6 C7 C9 . . . . 177.8(2) ?
    C6 C7 C8 C3 . . . . 5.3(3) ?
    C9 C7 C8 C3 . . . . -172.4(2) ?
    C6 C7 C8 S1 . . . . -175.15(17) ?
    C9 C7 C8 S1 . . . . 7.2(3) ?
    O1 C3 C8 C7 . . . . 171.1(2) ?
    C4 C3 C8 C7 . . . . -7.5(3) ?
    O1 C3 C8 S1 . . . . -8.5(3) ?
    C4 C3 C8 S1 . . . . 172.95(18) ?
    O3 S1 C8 C7 . . . . -107.6(2) ?
    O2 S1 C8 C7 . . . . 25.5(2) ?
    N1 S1 C8 C7 . . . . 139.78(19) ?
    O3 S1 C8 C3 . . . . 72.01(19) ?
    O2 S1 C8 C3 . . . . -154.89(17) ?
    N1 S1 C8 C3 . . . . -40.7(2) ?
    C6 C7 C9 F4 . . . . -138.2(2) ?
    C8 C7 C9 F4 . . . . 39.5(3) ?
    C6 C7 C9 F5 . . . . -18.2(3) ?
    C8 C7 C9 F5 . . . . 159.5(2) ?
    C6 C7 C9 F3 . . . . 99.7(3) ?
    C8 C7 C9 F3 . . . . -82.6(3) ?
    N4 N3 C10 N2 . . . . 0.0(3) ?
    N4 N3 C10 N1 . . . . -178.3(2) ?
    C11 N2 C10 N3 . . . . -0.2(3) ?
    C11 N2 C10 N1 . . . . 178.2(2) ?
    S1 N1 C10 N3 . . . . -39.4(3) ?
    S1 N1 C10 N2 . . . . 142.28(19) ?
    C10 N2 C11 N4 . . . . 0.4(3) ?
    C10 N2 C11 C12 . . . . 178.9(3) ?
    N3 N4 C11 N2 . . . . -0.4(3) ?
    C14 N4 C11 N2 . . . . 179.0(2) ?
    N3 N4 C11 C12 . . . . -179.2(2) ?
    C14 N4 C11 C12 . . . . 0.3(4) ?
    C15 O4 C12 C13 . . . . 2.7(4) ?
    C15 O4 C12 C11 . . . . -176.1(2) ?
    N2 C11 C12 C13 . . . . -178.4(3) ?
    N4 C11 C12 C13 . . . . 0.1(4) ?
    N2 C11 C12 O4 . . . . 0.6(4) ?
    N4 C11 C12 O4 . . . . 179.1(2) ?
    O4 C12 C13 N5 . . . . -178.9(3) ?
    C11 C12 C13 N5 . . . . 0.0(4) ?
    C14 N5 C13 C12 . . . . -0.4(4) ?
    C13 N5 C14 O5 . . . . -179.8(3) ?
    C13 N5 C14 N4 . . . . 0.7(4) ?
    C16 O5 C14 N5 . . . . 2.0(4) ?
    C16 O5 C14 N4 . . . . -178.4(2) ?
    C11 N4 C14 N5 . . . . -0.7(4) ?
    N3 N4 C14 N5 . . . . 178.7(2) ?
    C11 N4 C14 O5 . . . . 179.8(2) ?
    N3 N4 C14 O5 . . . . -0.9(4) ?
    C19 O6 C17 C18 . . . . 175.3(2) ?
    O6 C17 C18 F6 . . . . -61.3(3) ?
    O6 C17 C18 F7 . . . . 55.7(3) ?
    C17 O6 C19 C20 . . . . -4.0(3) ?
    C17 O6 C19 C24 . . . . 177.0(2) ?
    O6 C19 C20 C21 . . . . -176.2(2) ?
    C24 C19 C20 C21 . . . . 2.8(4) ?
    C19 C20 C21 C22 . . . . 3.3(4) ?
    C20 C21 C22 C23 . . . . -4.0(4) ?
    C21 C22 C23 C24 . . . . -1.5(4) ?
    C21 C22 C23 C25 . . . . 173.3(2) ?
    O6 C19 C24 C23 . . . . 171.0(2) ?
    C20 C19 C24 C23 . . . . -8.1(3) ?
    O6 C19 C24 S2 . . . . -11.3(3) ?
    C20 C19 C24 S2 . . . . 169.70(19) ?
    C22 C23 C24 C19 . . . . 7.4(3) ?
    C25 C23 C24 C19 . . . . -167.0(2) ?
    C22 C23 C24 S2 . . . . -170.27(18) ?
    C25 C23 C24 S2 . . . . 15.3(3) ?
    O7 S2 C24 C19 . . . . 71.2(2) ?
    O8 S2 C24 C19 . . . . -155.77(18) ?
    N6 S2 C24 C19 . . . . -41.5(2) ?
    O7 S2 C24 C23 . . . . -111.1(2) ?
    O8 S2 C24 C23 . . . . 21.9(2) ?
    N6 S2 C24 C23 . . . . 136.22(19) ?
    C22 C23 C25 F9 . . . . -138.3(2) ?
    C24 C23 C25 F9 . . . . 36.3(3) ?
    C22 C23 C25 F8 . . . . 97.3(3) ?
    C24 C23 C25 F8 . . . . -88.1(3) ?
    C22 C23 C25 F10 . . . . -20.8(3) ?
    C24 C23 C25 F10 . . . . 153.8(2) ?
    N9 N8 C26 N7 . . . . 0.1(3) ?
    N9 N8 C26 N6 . . . . -178.7(2) ?
    C27 N7 C26 N8 . . . . -0.5(3) ?
    C27 N7 C26 N6 . . . . 178.4(2) ?
    S2 N6 C26 N8 . . . . -36.0(3) ?
    S2 N6 C26 N7 . . . . 145.19(18) ?
    C26 N7 C27 N9 . . . . 0.6(2) ?
    C26 N7 C27 C28 . . . . 178.6(2) ?
    N8 N9 C27 N7 . . . . -0.7(3) ?
    C30 N9 C27 N7 . . . . 178.4(2) ?
    N8 N9 C27 C28 . . . . -178.9(2) ?
    C30 N9 C27 C28 . . . . 0.2(3) ?
    C31 O9 C28 C29 . . . . 3.1(4) ?
    C31 O9 C28 C27 . . . . -175.4(2) ?
    N7 C27 C28 C29 . . . . -177.5(2) ?
    N9 C27 C28 C29 . . . . 0.2(4) ?
    N7 C27 C28 O9 . . . . 1.2(4) ?
    N9 C27 C28 O9 . . . . 178.9(2) ?
    O9 C28 C29 N10 . . . . -179.1(2) ?
    C27 C28 C29 N10 . . . . -0.7(4) ?
    C30 N10 C29 C28 . . . . 0.7(4) ?
    C29 N10 C30 O10 . . . . -179.7(2) ?
    C29 N10 C30 N9 . . . . -0.3(4) ?
    C32 O10 C30 N10 . . . . 1.5(4) ?
    C32 O10 C30 N9 . . . . -178.0(2) ?
    C27 N9 C30 N10 . . . . -0.2(4) ?
    N8 N9 C30 N10 . . . . 178.7(2) ?
    C27 N9 C30 O10 . . . . 179.4(2) ?
    N8 N9 C30 O10 . . . . -1.8(4) ?
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
    C1 H1A F10 1_455 0.99 2.48 3.293(3) 138.9
    C16 H16C F3 2_566 0.98 2.40 3.185(3) 136.2
    C17 H17B O8 1_455 0.99 2.40 3.102(3) 127.0
    C18 H18 F10 1_465 1.00 2.60 3.104(3) 111.2
    C20 H20 F9 1_455 0.95 2.55 3.466(3) 161.7
    C32 H32C F8 2_855 0.98 2.36 3.146(3) 136.6
data_New_Global_Publ_Block
_journal_date_recd_electronic     2017-07-29
_journal_date_accepted     2017-08-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2017
_journal_volume     73
_journal_issue      9
_journal_page_first     1312
_journal_page_last     1315
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989017011458
_journal_coeditor_code     SJ5532
loop_
    _publ_contact_author_name
    _publ_contact_author_address
    _publ_contact_author_email
    'Kim, Tae Ho'
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
;
thkim@gnu.ac.kr
;
    'Kim, Jineun'
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
;
jekim@gnu.ac.kr
;
_publ_contact_author_fax     '+82-55-772-2789'
_publ_contact_author_phone     '+82-55-772-2789'
_publ_section_title
;
Crystal structure of penoxsulam
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Park, Hyunjin' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
    'Kim, Jineun' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
    'Chiang, Hojae' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
    'Kim, Tae Ho' .
;
Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences,
Gyeongsang National University, Jinju 52828,
Republic of Korea
;
_publ_section_synopsis
;
The herbicide penoxsulam  crystallizes with two independent molecules in the
asymmetric unit. The crystal structure is stabilized by C---F...π and π--π
interactions that combine with C---H...F and C---H O hydrogen bonds and weak
intermolecular F...F short contacts to form a three-dimensional network.
;
