##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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_D
_audit_creation_method     'from SHELXL97 CIF and IUCr SHELXL97-template'
_journal_date_recd_electronic     2008-04-23
_journal_date_accepted     2008-05-07
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      6
_journal_page_first     o1126
_journal_page_last     o1126
_journal_paper_category     QO
_journal_coeditor_code     HK2456
_publ_contact_author_name     ' Guo, Cheng'
_publ_contact_author_address
;
Department of Applied Chemistry
College of Science
Nanjing University of Technolgy
Xinmofan Road No.5 Nanjing
Nanjing 210009
People's Republic of China
;
_publ_contact_author_email     guocheng@njut.edu.cn
_publ_contact_author_fax     '86 25  83369345'
_publ_contact_author_phone     '86 25 83587448'
_publ_section_title
;\
Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-\
(methylsulfonyl)amino]pyrimidine-5-carboxylate
;
loop_
    _publ_author_name
    _publ_author_address
    'He, Wei'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Yang, Dong-Ling'
;
Nanjing Frochem Tech. Co. Ltd,
Xinmofan Road No. 36 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Cui, Yong-Tao'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Xu, Ye-Ming'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
    'Guo, Cheng'
;
Department of Applied Chemistry,
College of Science,
Nanjing University of Technolgy,
Xinmofan Road No. 5 Nanjing,
Nanjing 210009
People's Republic of China
;
_publ_section_synopsis
;
Methyl 4-(4-fluorophenyl)-6-isopropyl-2(N-methyl-N-methyl sulphonyl amino)
pyrimidine-5-carboxylate
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Methyl 4-(4-fluorophenyl)-6-isopropyl-2-[N-methyl-N-
(methylsulfonyl)amino]pyrimidine-5-carboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H20 F N3 O4 S'
_chemical_formula_sum     'C17 H20 F N3 O4 S'
_chemical_formula_iupac     'C17 H20 F N3 O4 S'
_chemical_formula_weight     381.42
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
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'
_cell_length_a     9.886(2)
_cell_length_b     9.988(2)
_cell_length_c     18.819(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1858.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     13
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.363
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     0.211
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North et al.,  1968)'
_exptl_absorpt_correction_T_min     0.9394
_exptl_absorpt_correction_T_max     0.9792
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method     'ω/2θ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3641
_diffrn_reflns_av_R_equivalents     0.0621
_diffrn_reflns_av_sigmaI/netI     0.0615
_diffrn_reflns_theta_min     2.16
_diffrn_reflns_theta_max     26.01
_diffrn_reflns_theta_full     26.01
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3641
_reflns_number_gt     2501
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1022
_refine_ls_R_factor_gt     0.0751
_refine_ls_wR_factor_gt     0.1659
_refine_ls_wR_factor_ref     0.1824
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.037
_refine_ls_number_reflns     3641
_refine_ls_number_parameters     235
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0700P)²+2.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.230
_refine_diff_density_min     -0.253
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983), 1755 Friedel pairs'
_refine_ls_abs_structure_Flack     0.14(16)
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     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXTL (Sheldrick, 2008)'
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 S 0.55906(13) 0.70239(15) 0.79080(8) 0.0491(4) Uani d . 1 . .
    O O1 0.8512(5) 1.1302(5) 0.5173(3) 0.0717(13) Uani d . 1 . .
    O O2 1.0367(4) 1.0166(5) 0.5494(2) 0.0611(12) Uani d . 1 . .
    O O3 0.5199(5) 0.5777(4) 0.8218(3) 0.0728(14) Uani d . 1 . .
    O O4 0.4566(4) 0.7948(5) 0.7692(2) 0.0672(14) Uani d . 1 . .
    N N1 0.6898(5) 0.8871(5) 0.6925(2) 0.0463(12) Uani d . 1 . .
    N N2 0.7773(4) 0.7113(4) 0.6207(2) 0.0396(10) Uani d . 1 . .
    N N3 0.6541(5) 0.6626(4) 0.7201(2) 0.0424(10) Uani d . 1 . .
    F F 1.1194(5) 0.5725(5) 0.3523(2) 0.1013(16) Uani d . 1 . .
    C C1 0.5763(7) 1.1558(7) 0.6613(5) 0.088(3) Uani d . 1 . .
    H H1B 0.5538 1.1425 0.6121 0.132 Uiso calc R 1 . .
    H H1C 0.5598 1.2474 0.6740 0.132 Uiso calc R 1 . .
    H H1D 0.5216 1.0982 0.6902 0.132 Uiso calc R 1 . .
    C C2 0.7657(9) 1.1427(7) 0.7496(4) 0.077(2) Uani d . 1 . .
    H H2B 0.8596 1.1213 0.7557 0.116 Uiso calc R 1 . .
    H H2C 0.7119 1.0853 0.7792 0.116 Uiso calc R 1 . .
    H H2D 0.7505 1.2344 0.7628 0.116 Uiso calc R 1 . .
    C C3 0.7266(6) 1.1227(6) 0.6731(3) 0.0476(13) Uani d . 1 . .
    H H3B 0.7820 1.1812 0.6431 0.057 Uiso calc R 1 . .
    C C4 0.7495(6) 0.9773(5) 0.6511(3) 0.0407(12) Uani d . 1 . .
    C C5 0.7091(5) 0.7596(6) 0.6763(3) 0.0414(12) Uani d . 1 . .
    C C6 0.8381(5) 0.8018(5) 0.5786(3) 0.0384(11) Uani d . 1 . .
    C C7 0.8293(5) 0.9380(5) 0.5933(3) 0.0409(12) Uani d . 1 . .
    C C8 0.9025(6) 1.0407(6) 0.5488(3) 0.0475(13) Uani d . 1 . .
    C C9 1.1203(7) 1.0930(8) 0.5012(4) 0.082(2) Uani d . 1 . .
    H H9A 1.2130 1.0661 0.5064 0.123 Uiso calc R 1 . .
    H H9B 1.1119 1.1866 0.5118 0.123 Uiso calc R 1 . .
    H H9C 1.0916 1.0770 0.4532 0.123 Uiso calc R 1 . .
    C C10 0.6696(6) 0.7803(7) 0.8495(3) 0.0590(17) Uani d . 1 . .
    H H10A 0.6214 0.8067 0.8915 0.088 Uiso calc R 1 . .
    H H10B 0.7080 0.8581 0.8272 0.088 Uiso calc R 1 . .
    H H10C 0.7407 0.7193 0.8621 0.088 Uiso calc R 1 . .
    C C11 0.6988(7) 0.5213(5) 0.7138(4) 0.0561(16) Uani d . 1 . .
    H H11A 0.7529 0.5111 0.6717 0.084 Uiso calc R 1 . .
    H H11B 0.6211 0.4640 0.7107 0.084 Uiso calc R 1 . .
    H H11C 0.7515 0.4974 0.7547 0.084 Uiso calc R 1 . .
    C C12 0.9120(6) 0.7448(6) 0.5171(3) 0.0448(13) Uani d . 1 . .
    C C13 0.9775(6) 0.6210(6) 0.5252(3) 0.0517(14) Uani d . 1 . .
    H H13A 0.9724 0.5762 0.5684 0.062 Uiso calc R 1 . .
    C C14 1.0499(7) 0.5646(7) 0.4695(3) 0.0630(17) Uani d . 1 . .
    H H14A 1.0974 0.4851 0.4756 0.076 Uiso calc R 1 . .
    C C15 1.0497(7) 0.6284(7) 0.4061(4) 0.0628(18) Uani d . 1 . .
    C C16 0.9852(7) 0.7473(7) 0.3944(3) 0.0601(17) Uani d . 1 . .
    H H16A 0.9877 0.7878 0.3499 0.072 Uiso calc R 1 . .
    C C17 0.9152(6) 0.8071(7) 0.4507(3) 0.0534(15) Uani d . 1 . .
    H H17A 0.8709 0.8882 0.4438 0.064 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    S 0.0363(6) 0.0583(8) 0.0528(8) -0.0070(7) 0.0064(7) 0.0028(8)
    O1 0.079(3) 0.059(3) 0.077(3) 0.018(3) 0.013(3) 0.031(2)
    O2 0.050(2) 0.082(3) 0.051(2) -0.014(2) 0.006(2) 0.012(2)
    O3 0.071(3) 0.062(3) 0.086(3) -0.019(2) 0.018(3) 0.009(3)
    O4 0.039(2) 0.073(3) 0.090(4) 0.012(2) 0.006(2) 0.012(3)
    N1 0.045(3) 0.046(3) 0.048(3) 0.002(2) 0.004(2) -0.003(2)
    N2 0.043(2) 0.031(2) 0.045(2) 0.0016(19) -0.005(2) -0.001(2)
    N3 0.048(2) 0.038(2) 0.041(2) 0.000(2) 0.002(2) 0.005(2)
    F 0.117(4) 0.110(3) 0.076(3) 0.019(3) 0.038(3) -0.036(3)
    C1 0.072(5) 0.048(4) 0.143(8) 0.024(4) -0.022(5) -0.020(5)
    C2 0.114(7) 0.048(4) 0.070(4) 0.011(4) -0.024(5) -0.012(3)
    C3 0.049(3) 0.040(3) 0.054(3) -0.001(3) 0.002(3) 0.000(3)
    C4 0.040(3) 0.042(3) 0.040(3) -0.001(2) -0.001(2) 0.005(2)
    C5 0.033(3) 0.047(3) 0.044(3) 0.006(2) -0.001(2) 0.007(3)
    C6 0.035(3) 0.043(3) 0.038(3) 0.011(2) -0.004(2) 0.003(2)
    C7 0.035(3) 0.044(3) 0.044(3) 0.003(3) -0.005(2) 0.007(2)
    C8 0.049(3) 0.047(3) 0.047(3) 0.002(3) 0.001(3) 0.001(3)
    C9 0.064(5) 0.110(7) 0.072(5) -0.033(5) 0.014(4) 0.021(5)
    C10 0.056(4) 0.082(5) 0.039(3) -0.011(3) 0.004(3) -0.005(3)
    C11 0.072(4) 0.032(3) 0.064(4) 0.004(3) 0.001(3) -0.001(3)
    C12 0.050(3) 0.041(3) 0.043(3) 0.008(3) 0.001(3) -0.007(3)
    C13 0.053(3) 0.052(3) 0.051(3) 0.003(3) 0.007(3) -0.003(3)
    C14 0.064(4) 0.066(4) 0.059(4) 0.006(4) 0.014(3) -0.005(3)
    C15 0.062(4) 0.071(4) 0.055(4) -0.003(4) 0.014(3) -0.017(4)
    C16 0.067(4) 0.069(4) 0.044(3) 0.004(4) 0.012(3) -0.003(3)
    C17 0.053(4) 0.064(4) 0.044(3) 0.010(3) 0.005(3) -0.003(3)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s.
planes) are estimated using the full covariance matrix. The cell e.s.d.'s
are taken into account individually in the estimation of e.s.d.'s in
distances, angles and torsion angles; correlations between e.s.d.'s in
cell parameters are only used when they are defined by crystal symmetry.
An approximate (isotropic) treatment of cell e.s.d.'s is used for
estimating e.s.d.'s 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
    S O3 . 1.428(4) ?
    S O4 . 1.429(4) ?
    S N3 . 1.677(5) ?
    S C10 . 1.738(6) ?
    O1 C8 . 1.187(7) ?
    O2 C8 . 1.348(7) ?
    O2 C9 . 1.446(7) ?
    N1 C4 . 1.329(7) ?
    N1 C5 . 1.324(7) ?
    N2 C5 . 1.335(7) ?
    N2 C6 . 1.345(6) ?
    N3 C5 . 1.384(7) ?
    N3 C11 . 1.483(6) ?
    F C15 . 1.346(7) ?
    C1 C3 . 1.538(9) ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C1 H1D . 0.9600 ?
    C2 C3 . 1.505(9) ?
    C2 H2B . 0.9600 ?
    C2 H2C . 0.9600 ?
    C2 H2D . 0.9600 ?
    C3 C4 . 1.526(8) ?
    C3 H3B . 0.9800 ?
    C4 C7 . 1.399(7) ?
    C6 C7 . 1.392(7) ?
    C6 C12 . 1.481(7) ?
    C7 C8 . 1.509(8) ?
    C9 H9A . 0.9600 ?
    C9 H9B . 0.9600 ?
    C9 H9C . 0.9600 ?
    C10 H10A . 0.9600 ?
    C10 H10B . 0.9600 ?
    C10 H10C . 0.9600 ?
    C11 H11A . 0.9600 ?
    C11 H11B . 0.9600 ?
    C11 H11C . 0.9600 ?
    C12 C13 . 1.404(8) ?
    C12 C17 . 1.398(8) ?
    C13 C14 . 1.389(8) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.353(9) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.366(9) ?
    C16 C17 . 1.398(8) ?
    C16 H16A . 0.9300 ?
    C17 H17A . 0.9300 ?
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
    O4 S O3 . . 119.2(3) ?
    O4 S N3 . . 109.0(3) ?
    O3 S N3 . . 105.6(3) ?
    O4 S C10 . . 109.7(3) ?
    O3 S C10 . . 107.6(3) ?
    N3 S C10 . . 104.9(3) ?
    C8 O2 C9 . . 117.6(5) ?
    C5 N1 C4 . . 117.0(5) ?
    C5 N2 C6 . . 116.4(4) ?
    C5 N3 C11 . . 120.1(5) ?
    C5 N3 S . . 121.8(4) ?
    C11 N3 S . . 117.2(4) ?
    C3 C1 H1B . . 109.5 ?
    C3 C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    C3 C1 H1D . . 109.5 ?
    H1B C1 H1D . . 109.5 ?
    H1C C1 H1D . . 109.5 ?
    C3 C2 H2B . . 109.5 ?
    C3 C2 H2C . . 109.5 ?
    H2B C2 H2C . . 109.5 ?
    C3 C2 H2D . . 109.5 ?
    H2B C2 H2D . . 109.5 ?
    H2C C2 H2D . . 109.5 ?
    C2 C3 C4 . . 110.4(5) ?
    C2 C3 C1 . . 111.0(6) ?
    C4 C3 C1 . . 108.0(5) ?
    C2 C3 H3B . . 109.1 ?
    C4 C3 H3B . . 109.1 ?
    C1 C3 H3B . . 109.1 ?
    N1 C4 C7 . . 121.0(5) ?
    N1 C4 C3 . . 114.8(5) ?
    C7 C4 C3 . . 124.2(5) ?
    N1 C5 N2 . . 126.9(5) ?
    N1 C5 N3 . . 118.7(5) ?
    N2 C5 N3 . . 114.3(5) ?
    N2 C6 C7 . . 120.8(5) ?
    N2 C6 C12 . . 115.0(5) ?
    C7 C6 C12 . . 124.2(5) ?
    C6 C7 C4 . . 117.7(5) ?
    C6 C7 C8 . . 121.6(5) ?
    C4 C7 C8 . . 120.7(5) ?
    O1 C8 O2 . . 124.0(6) ?
    O1 C8 C7 . . 125.8(6) ?
    O2 C8 C7 . . 110.2(5) ?
    O2 C9 H9A . . 109.5 ?
    O2 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    O2 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    S C10 H10A . . 109.5 ?
    S C10 H10B . . 109.5 ?
    H10A C10 H10B . . 109.5 ?
    S C10 H10C . . 109.5 ?
    H10A C10 H10C . . 109.5 ?
    H10B C10 H10C . . 109.5 ?
    N3 C11 H11A . . 109.5 ?
    N3 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    N3 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    C17 C12 C13 . . 118.6(5) ?
    C17 C12 C6 . . 122.6(5) ?
    C13 C12 C6 . . 118.8(5) ?
    C14 C13 C12 . . 120.9(6) ?
    C14 C13 H13A . . 119.6 ?
    C12 C13 H13A . . 119.6 ?
    C15 C14 C13 . . 118.3(7) ?
    C15 C14 H14A . . 120.8 ?
    C13 C14 H14A . . 120.8 ?
    F C15 C14 . . 117.8(6) ?
    F C15 C16 . . 118.7(6) ?
    C14 C15 C16 . . 123.5(6) ?
    C15 C16 C17 . . 118.8(6) ?
    C15 C16 H16A . . 120.6 ?
    C17 C16 H16A . . 120.6 ?
    C12 C17 C16 . . 119.9(6) ?
    C12 C17 H17A . . 120.1 ?
    C16 C17 H17A . . 120.1 ?
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
    O4 S N3 C5 . . . . 50.2(5) ?
    O3 S N3 C5 . . . . 179.3(4) ?
    C10 S N3 C5 . . . . -67.2(5) ?
    O4 S N3 C11 . . . . -141.0(4) ?
    O3 S N3 C11 . . . . -12.0(5) ?
    C10 S N3 C11 . . . . 101.5(5) ?
    C9 O2 C8 O1 . . . . -8.8(9) ?
    C9 O2 C8 C7 . . . . 171.1(5) ?
    C5 N1 C4 C7 . . . . -0.2(8) ?
    C5 N1 C4 C3 . . . . -178.7(5) ?
    C4 N1 C5 N2 . . . . -3.3(8) ?
    C4 N1 C5 N3 . . . . 176.9(5) ?
    C6 N2 C5 N1 . . . . 3.3(8) ?
    C6 N2 C5 N3 . . . . -176.9(4) ?
    C5 N2 C6 C7 . . . . 0.3(7) ?
    C5 N2 C6 C12 . . . . -179.5(4) ?
    S N3 C5 N1 . . . . 2.5(7) ?
    S N3 C5 N2 . . . . -177.3(4) ?
    C11 N3 C5 N1 . . . . -165.9(5) ?
    C11 N3 C5 N2 . . . . 14.2(7) ?
    C2 C3 C4 N1 . . . . 53.8(7) ?
    C1 C3 C4 N1 . . . . -67.7(7) ?
    C2 C3 C4 C7 . . . . -124.6(6) ?
    C1 C3 C4 C7 . . . . 113.9(7) ?
    N1 C4 C7 C6 . . . . 3.3(8) ?
    C3 C4 C7 C6 . . . . -178.4(5) ?
    N1 C4 C7 C8 . . . . -176.9(5) ?
    C3 C4 C7 C8 . . . . 1.4(8) ?
    N2 C6 C7 C4 . . . . -3.3(7) ?
    C12 C6 C7 C4 . . . . 176.5(5) ?
    N2 C6 C7 C8 . . . . 176.9(5) ?
    C12 C6 C7 C8 . . . . -3.3(8) ?
    N2 C6 C12 C17 . . . . 143.1(6) ?
    C7 C6 C12 C17 . . . . -36.7(8) ?
    N2 C6 C12 C13 . . . . -34.7(7) ?
    C7 C6 C12 C13 . . . . 145.5(6) ?
    C6 C7 C8 O1 . . . . 121.1(7) ?
    C4 C7 C8 O1 . . . . -58.6(8) ?
    C6 C7 C8 O2 . . . . -58.8(7) ?
    C4 C7 C8 O2 . . . . 121.5(6) ?
    C17 C12 C13 C14 . . . . 3.2(9) ?
    C6 C12 C13 C14 . . . . -178.9(6) ?
    C13 C12 C17 C16 . . . . -1.3(9) ?
    C6 C12 C17 C16 . . . . -179.1(6) ?
    C12 C13 C14 C15 . . . . -3.5(10) ?
    C13 C14 C15 F . . . . -179.6(6) ?
    C13 C14 C15 C16 . . . . 1.9(11) ?
    C14 C15 C16 C17 . . . . -0.1(11) ?
    F C15 C16 C17 . . . . -178.6(6) ?
    C15 C16 C17 C12 . . . . -0.2(10) ?
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
    C3 H3B O1 . 0.98 2.52 3.181(8) 125.00
    C10 H10B N1 . 0.96 2.56 3.148(7) 120.00
    C11 H11A N2 . 0.96 2.23 2.697(7) 109.00
    C11 H11C F 2_765 0.96 2.34 3.302(8) 177.00
