##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELX-97
_journal_data_validation_number     ?
_journal_date_recd_electronic     2007-08-13
_journal_date_accepted     2007-08-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      9
_journal_page_first     o3918
_journal_page_last     o3919
_journal_paper_category     QO
_journal_coeditor_code     LH2481
_publ_contact_author_name     'Dr Alastair J. Florence'
_publ_contact_author_address
;
Solid-State Research Group
Strathclyde Institute of Pharmacy and Biomedical Sciences
The John Arbuthnott Building
University of Strathclyde
27 Taylor Street
Glasgow G4 0NR, U.K.
;
_publ_contact_author_email     alastair.florence@strath.ac.uk
_publ_contact_author_fax     '01415522562'
_publ_contact_author_phone     '01415484877'
_publ_section_title
;
10,11-Dihydrocarbamazepine--dimethyl sulfoxide (1/1)
;
loop_
    _publ_author_name
    _publ_author_address
    'Johnston, Andrea'
;
Solid-State Research Group
Strathclyde Institute of Pharmacy and Biomedical Sciences
The John Arbuthnott Building
University of Strathclyde
27 Taylor Street
Glasgow G4 0NR
Scotland
;
    'Florence, Alastair J.'
;
Solid-State Research Group
Strathclyde Institute of Pharmacy and Biomedical Sciences
The John Arbuthnott Building
University of Strathclyde
27 Taylor Street
Glasgow G4 0NR
Scotland
;
    'Shankland, Kenneth'
;
ISIS Facility
Rutherford Appleton Laboratory
Chilton, Didcot
Oxon OX11 0QX
England
;
    'Leech, Charlotte K.'
;
ISIS Facility
Rutherford Appleton Laboratory
Chilton, Didcot
Oxon OX11 0QX
England
;
    'Shankland, Norman'
;
Solid-State Research Group
Strathclyde Institute of Pharmacy and Biomedical Sciences
The John Arbuthnott Building
University of Strathclyde
27 Taylor Street
Glasgow G4 0NR
Scotland
;
    'Fernandes, Philippe'
;
Solid-State Research Group
Strathclyde Institute of Pharmacy and Biomedical Sciences
The John Arbuthnott Building
University of Strathclyde
27 Taylor Street
Glasgow G4 0NR
Scotland
;
data_I
_chemical_name_systematic
;
10,11-dihydro-5H-dibenz[b,f]azepine-5-carboxamide--dimethyl
sulfoxide (1/1)
;
_chemical_name_common     '10,11-Dihydrocarbamazepine--dimethyl sulfoxide (1/1)'
_chemical_formula_moiety     'C15 H14 N2 O1, C2 H6 O S'
_chemical_formula_sum     'C17 H20 N2 O2 S'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C15 H14 N2 O1, C2 H6 O S'
_chemical_formula_weight     316.41
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x,1/2+y,1/2-z'
    '-x,-y,-z'
    'x,1/2-y,1/2+z'
_cell_length_a     10.2696(3)
_cell_length_b     6.8543(2)
_cell_length_c     23.3599(6)
_cell_angle_alpha     90.00
_cell_angle_beta     98.932(2)
_cell_angle_gamma     90.00
_cell_volume     1624.39(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7414
_cell_measurement_theta_min     2.6333
_cell_measurement_theta_max     28.5896
_cell_measurement_temperature     123(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.07
_exptl_crystal_size_rad     ?
_exptl_crystal_density_diffrn     1.294
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     0.208
_exptl_absorpt_correction_type     'analytical'
_exptl_absorpt_process_details
       '[CrysAlis RED (Oxford Diffraction, 2000), based on Clark & Reid (1995)]'
_exptl_absorpt_correction_T_min     0.9518
_exptl_absorpt_correction_T_max     0.9856
_exptl_special_details
;
Absorption correction:
CrysAlis RED (Oxford Diffraction, 2000), analytical numeric absorption
correction using a multifaceted crystal model based on expressions derived
by  Clark & Reid (1995).
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.
;
_diffrn_ambient_temperature     123(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Enhance (Mu) X-ray Source'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction Gemini'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     15.9745
_diffrn_reflns_number     16299
_diffrn_reflns_av_R_equivalents     0.0290
_diffrn_reflns_av_sigmaI/netI     0.0248
_diffrn_reflns_theta_min     2.87
_diffrn_reflns_theta_max     26.37
_diffrn_reflns_theta_full     26.37
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -29
_diffrn_reflns_limit_l_max     29
_diffrn_reflns_reduction_process     ?
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    ? ? ?
_refine_special_details
;
 The structure was refined using a disordered model in which the relative
 occupancy of the major component equals 81.1(6)%.  The disordered model
 is justified by the fact the refined structure using an ordered model
 showed 1) large residual peaks of electron density
 close to the C7-C8 bond which were assigned as atoms C7a and C8a, and
 2) anomalous adps especially for atoms C3 C4 C5 and C12 C13 C14.  Inclusion
 of disorder yielded adp values within normal ranges for these atoms. Overall,
 the disordered model resulted in significant improvements in the
 Rfactors (wR2 = 0.1426 and R1 = 0.0551 with no disorder).
 The major and minor components of the disorder are related conformers of
 DHC. The two confomers are related by an approximate inversion of the
 C6-C7-C8-C9  torsion angle, which leads to an associated shift
 in the position of the aromatic rings. This relationship can also be
 described as an approximate 180° rotation about the N1-C15 bond
 followed by an inversion of the whole molecule (note SG=P21/c contains an
 inversion center).
 For the major component of the disorder and for the undisordered part of
 the structure all non-hydrogen atoms were located from the direct method
 solution, all hydrogen atoms were visible in the Fourier difference map,
 the NH2 hydrogen atoms located from the Fourier difference map and the
 atomic coordinated and Uiso refined freely, the rest of the hydrogen
 atoms were constrained to geometrically sensible positions with a riding
 model (SHELX-97).
 For the minor component of the disorder atoms C7A and C8A were visible in
 the Fourier difference map. The aromatic rings were constrained to a
 regular hexagon with C-C bond lenght of 1.39Å and all hydrogen atoms were
 constrained to geometrically sensible positions with a riding model
 (SHELX-97). All atoms in the minor component of the disorder were refined
 isotropically with Uiso constrained to be identical for all the carbon atoms.
 The Uiso for the hydrogen atoms was constrained to be 1.2 times the value
 for the hydrogen atoms.
;
_reflns_number_total     3326
_reflns_number_gt     2627
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0576
_refine_ls_R_factor_gt     0.0421
_refine_ls_wR_factor_all     ?
_refine_ls_wR_factor_ref     0.1137
_refine_ls_goodness_of_fit_all     ?
_refine_ls_goodness_of_fit_ref     1.055
_refine_ls_restrained_S_all     1.056
_refine_ls_restrained_S_obs     ?
_refine_ls_number_reflns     3326
_refine_ls_number_parameters     223
_refine_ls_number_restraints     2
_refine_ls_number_constraints     ?
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0295P)²+2.9523P] where P=(Fo²+2Fc²)/3'
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.705
_refine_diff_density_min     -0.386
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     ?
_refine_ls_abs_structure_Flack     ?
_refine_ls_abs_structure_Rogers     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'Cl' 'Cl' 0.1484 0.1585
                         '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'
    'O' 'O' 0.0106 0.0060
                         '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'
    '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'
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2000)
;
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2000)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2000)
;
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'PLATON (Spek, 2003)'
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
    O O1 1.05951(11) 0.08903(17) 0.43941(5) 0.0227(3) Uani d . 1 . .
    N N1 0.91771(13) 0.2552(2) 0.37293(6) 0.0189(3) Uani d . 1 A .
    C C15 0.94794(15) 0.1576(2) 0.42506(7) 0.0189(3) Uani d . 1 . .
    N N2 0.85194(15) 0.1394(2) 0.45751(7) 0.0236(3) Uani d . 1 . .
    H H2A 0.871(2) 0.077(3) 0.4893(10) 0.038(6) Uiso d . 1 . .
    H H2B 0.778(2) 0.186(3) 0.4494(9) 0.034(6) Uiso d . 1 . .
    C C1 1.02405(15) 0.3029(3) 0.34188(7) 0.0207(4) Uani d G 1 . .
    C C2A 1.0637(9) 0.1930(9) 0.2976(3) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H2C 1.0215 0.0725 0.2866 0.024 Uiso calc PR 0.189(6) A 2
    C C3A 1.1650(10) 0.2595(14) 0.2696(4) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H3A 1.1921 0.1844 0.2393 0.024 Uiso calc PR 0.189(6) A 2
    C C4A 1.2268(7) 0.4358(15) 0.2858(4) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H4A 1.2961 0.4812 0.2666 0.024 Uiso calc PR 0.189(6) A 2
    C C5A 1.1872(9) 0.5457(12) 0.3300(5) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H5A 1.2294 0.6662 0.3411 0.024 Uiso calc PR 0.189(6) A 2
    C C6A 1.0858(8) 0.4793(8) 0.3581(3) 0.0203(13) Uiso d PGD 0.189(6) A 2
    C C2 1.0568(3) 0.1613(4) 0.30398(11) 0.0264(6) Uani d P 0.811(6) A 1
    H H2 1.0115 0.0400 0.3006 0.032 Uiso calc PR 0.811(6) A 1
    C C3 1.1561(3) 0.1974(5) 0.27098(11) 0.0300(7) Uani d P 0.811(6) A 1
    H H3 1.1799 0.1006 0.2454 0.036 Uiso calc PR 0.811(6) A 1
    C C4 1.2193(2) 0.3749(5) 0.27597(11) 0.0293(7) Uani d P 0.811(6) A 1
    H H4 1.2868 0.4012 0.2534 0.035 Uiso calc PR 0.811(6) A 1
    C C5 1.1859(2) 0.5136(4) 0.31305(13) 0.0313(7) Uani d P 0.811(6) A 1
    H H5 1.2310 0.6351 0.3157 0.038 Uiso calc PR 0.811(6) A 1
    C C6 1.0874(3) 0.4829(4) 0.34740(11) 0.0272(6) Uani d P 0.811(6) A 1
    C C7 1.0555(3) 0.6467(4) 0.38578(16) 0.0365(7) Uani d P 0.811(6) A 1
    H H7A 1.0392 0.7646 0.3613 0.044 Uiso calc PR 0.811(6) A 1
    H H7B 1.1357 0.6724 0.4142 0.044 Uiso calc PR 0.811(6) A 1
    C C8 0.9413(3) 0.6269(4) 0.41943(13) 0.0293(7) Uani d P 0.811(6) A 1
    H H8A 0.9644 0.5291 0.4505 0.035 Uiso calc PR 0.811(6) A 1
    H H8B 0.9274 0.7533 0.4380 0.035 Uiso calc PR 0.811(6) A 1
    C C9 0.8147(2) 0.5664(3) 0.38213(10) 0.0233(5) Uani d P 0.811(6) A 1
    C C10 0.80304(16) 0.3762(3) 0.36009(7) 0.0217(4) Uani d G 1 . .
    C C11A 0.6944(4) 0.2697(6) 0.3343(3) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H11A 0.7023 0.1334 0.3283 0.024 Uiso calc PR 0.189(6) A 2
    C C12A 0.5743(3) 0.3626(12) 0.3173(4) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H12A 0.5001 0.2898 0.2996 0.024 Uiso calc PR 0.189(6) A 2
    C C13A 0.5629(4) 0.5620(12) 0.3261(4) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H13A 0.4808 0.6255 0.3144 0.024 Uiso calc PR 0.189(6) A 2
    C C14A 0.6715(7) 0.6686(7) 0.3519(4) 0.0203(13) Uiso d PG 0.189(6) A 2
    H H14A 0.6636 0.8049 0.3579 0.024 Uiso calc PR 0.189(6) A 2
    C C9A 0.7916(5) 0.5757(3) 0.3689(3) 0.0203(13) Uiso d PGD 0.189(6) A 2
    C C7A 1.0462(10) 0.5949(16) 0.4089(4) 0.0203(13) Uiso d PD 0.189(6) A 2
    H H7C 1.0466 0.5061 0.4423 0.024 Uiso calc PR 0.189(6) A 2
    H H7D 1.1127 0.6979 0.4204 0.024 Uiso calc PR 0.189(6) A 2
    C C8A 0.9104(8) 0.6895(16) 0.3947(5) 0.0203(13) Uiso d PD 0.189(6) A 2
    H H8C 0.8902 0.7477 0.4311 0.024 Uiso calc PR 0.189(6) A 2
    H H8D 0.9191 0.7991 0.3680 0.024 Uiso calc PR 0.189(6) A 2
    C C11 0.6906(2) 0.3133(5) 0.32519(11) 0.0319(6) Uani d P 0.811(6) A 1
    H H11 0.6850 0.1841 0.3103 0.038 Uiso calc PR 0.811(6) A 1
    C C12 0.5857(2) 0.4407(6) 0.31199(11) 0.0406(8) Uani d P 0.811(6) A 1
    H H12 0.5074 0.3989 0.2880 0.049 Uiso calc PR 0.811(6) A 1
    C C13 0.5945(3) 0.6268(5) 0.33340(12) 0.0397(8) Uani d P 0.811(6) A 1
    H H13 0.5221 0.7134 0.3241 0.048 Uiso calc PR 0.811(6) A 1
    C C14 0.7070(3) 0.6901(4) 0.36816(12) 0.0338(7) Uani d P 0.811(6) A 1
    H H14 0.7112 0.8197 0.3828 0.041 Uiso calc PR 0.811(6) A 1
    S S1 0.43861(4) 0.26487(8) 0.43255(2) 0.03643(17) Uani d . 1 . .
    O O2 0.57765(12) 0.2223(2) 0.46042(6) 0.0429(4) Uani d . 1 . .
    C C17 0.3694(2) 0.0384(4) 0.40614(10) 0.0453(6) Uani d . 1 . .
    H H17A 0.4117 -0.0051 0.3736 0.068 Uiso calc R 1 . .
    H H17B 0.2746 0.0546 0.3931 0.068 Uiso calc R 1 . .
    H H17C 0.3836 -0.0591 0.4372 0.068 Uiso calc R 1 . .
    C C16 0.34591(19) 0.2887(3) 0.49031(10) 0.0412(5) Uani d . 1 . .
    H H16A 0.3713 0.4093 0.5117 0.062 Uiso calc R 1 . .
    H H16B 0.3635 0.1768 0.5165 0.062 Uiso calc R 1 . .
    H H16C 0.2517 0.2932 0.4746 0.062 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
    O1 0.0168(6) 0.0253(6) 0.0260(6) 0.0016(5) 0.0037(5) 0.0045(5)
    N1 0.0165(7) 0.0214(7) 0.0193(7) 0.0003(5) 0.0043(5) 0.0004(6)
    C15 0.0188(8) 0.0153(8) 0.0223(8) -0.0026(6) 0.0023(6) -0.0015(7)
    N2 0.0182(8) 0.0283(8) 0.0250(8) 0.0038(6) 0.0055(6) 0.0081(7)
    C1 0.0156(8) 0.0288(9) 0.0171(8) 0.0000(7) 0.0005(6) 0.0027(7)
    C2 0.0210(11) 0.0389(14) 0.0193(11) -0.0028(10) 0.0036(8) -0.0018(10)
    C3 0.0252(12) 0.0462(18) 0.0188(11) 0.0003(12) 0.0038(8) -0.0010(12)
    C4 0.0195(11) 0.0475(19) 0.0209(12) -0.0017(11) 0.0031(9) 0.0063(11)
    C5 0.0226(11) 0.0370(15) 0.0339(16) -0.0070(11) 0.0031(12) 0.0069(12)
    C6 0.0211(11) 0.0333(13) 0.0270(13) -0.0001(9) 0.0031(10) 0.0036(10)
    C7 0.0360(14) 0.0286(14) 0.0456(18) -0.0076(11) 0.0091(12) -0.0032(12)
    C8 0.0363(14) 0.0229(13) 0.0293(14) -0.0010(10) 0.0072(11) -0.0035(11)
    C9 0.0259(12) 0.0280(12) 0.0183(11) 0.0073(9) 0.0103(9) 0.0088(9)
    C10 0.0207(8) 0.0290(9) 0.0164(8) 0.0042(7) 0.0064(6) 0.0042(7)
    C11 0.0231(12) 0.0472(16) 0.0242(12) 0.0054(10) -0.0003(9) -0.0023(11)
    C12 0.0234(12) 0.068(2) 0.0288(14) 0.0095(13) -0.0005(10) 0.0042(15)
    C13 0.0337(15) 0.0553(19) 0.0314(14) 0.0211(14) 0.0092(12) 0.0109(13)
    C14 0.0388(15) 0.0398(15) 0.0258(14) 0.0160(11) 0.0142(11) 0.0118(11)
    S1 0.0212(3) 0.0496(3) 0.0390(3) 0.0011(2) 0.00652(19) 0.0107(2)
    O2 0.0173(7) 0.0631(10) 0.0486(9) -0.0003(6) 0.0059(6) 0.0105(8)
    C17 0.0315(11) 0.0599(15) 0.0430(12) 0.0056(10) 0.0013(9) -0.0136(11)
    C16 0.0253(10) 0.0509(14) 0.0488(12) -0.0079(9) 0.0098(9) -0.0113(10)
_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
    O1 C15 . 1.2357(19) ?
    N1 C15 . 1.382(2) ?
    N1 C10 . 1.434(2) ?
    N1 C1 . 1.439(2) ?
    C15 N2 . 1.339(2) ?
    N2 H2A . 0.85(2) ?
    N2 H2B . 0.82(2) ?
    C1 C2 . 1.390(3) ?
    C1 C2A . 1.3900 ?
    C1 C6A . 1.3900 ?
    C1 C6 . 1.391(3) ?
    C2A C3A . 1.3900 ?
    C2A H2C . 0.9500 ?
    C3A C4A . 1.3900 ?
    C3A H3A . 0.9500 ?
    C4A C5A . 1.3900 ?
    C4A H4A . 0.9500 ?
    C5A C6A . 1.3900 ?
    C5A H5A . 0.9500 ?
    C6A C7A . 1.533(8) ?
    C2 C3 . 1.393(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.376(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.365(4) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.401(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.504(3) ?
    C7 C8 . 1.516(4) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.507(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C14 . 1.392(3) ?
    C9 C10 . 1.399(3) ?
    C10 C11 . 1.376(3) ?
    C10 C11A . 1.3900 ?
    C10 C9A . 1.3900 ?
    C11A C12A . 1.3900 ?
    C11A H11A . 0.9500 ?
    C12A C13A . 1.3900 ?
    C12A H12A . 0.9500 ?
    C13A C14A . 1.3900 ?
    C13A H13A . 0.9500 ?
    C14A C9A . 1.3900 ?
    C14A H14A . 0.9500 ?
    C9A C8A . 1.494(7) ?
    C7A C8A . 1.527(14) ?
    C7A H7C . 0.9900 ?
    C7A H7D . 0.9900 ?
    C8A H8C . 0.9900 ?
    C8A H8D . 0.9900 ?
    C11 C12 . 1.384(4) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.368(4) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.375(4) ?
    C13 H13 . 0.9500 ?
    C14 H14 . 0.9500 ?
    S1 O2 . 1.5030(14) ?
    S1 C16 . 1.776(2) ?
    S1 C17 . 1.777(2) ?
    C17 H17A . 0.9800 ?
    C17 H17B . 0.9800 ?
    C17 H17C . 0.9800 ?
    C16 H16A . 0.9800 ?
    C16 H16B . 0.9800 ?
    C16 H16C . 0.9800 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    ? ? ? ? ? ?
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
    C15 N1 C10 . . 121.95(13) ?
    C15 N1 C1 . . 118.02(13) ?
    C10 N1 C1 . . 115.22(13) ?
    O1 C15 N2 . . 122.95(16) ?
    O1 C15 N1 . . 119.68(14) ?
    N2 C15 N1 . . 117.36(14) ?
    C15 N2 H2A . . 116.5(14) ?
    C15 N2 H2B . . 124.7(15) ?
    H2A N2 H2B . . 119(2) ?
    C2 C1 C6A . . 129.5(3) ?
    C2A C1 C6A . . 120.0 ?
    C2 C1 C6 . . 121.50(18) ?
    C2A C1 C6 . . 111.3(3) ?
    C2 C1 N1 . . 116.10(17) ?
    C2A C1 N1 . . 125.7(3) ?
    C6A C1 N1 . . 114.2(3) ?
    C6 C1 N1 . . 122.35(17) ?
    C1 C2A C3A . . 120.0 ?
    C1 C2A H2C . . 120.0 ?
    C3A C2A H2C . . 120.0 ?
    C2A C3A C4A . . 120.0 ?
    C2A C3A H3A . . 120.0 ?
    C4A C3A H3A . . 120.0 ?
    C3A C4A C5A . . 120.0 ?
    C3A C4A H4A . . 120.0 ?
    C5A C4A H4A . . 120.0 ?
    C6A C5A C4A . . 120.0 ?
    C6A C5A H5A . . 120.0 ?
    C4A C5A H5A . . 120.0 ?
    C5A C6A C1 . . 120.0 ?
    C5A C6A C7A . . 120.2(5) ?
    C1 C6A C7A . . 119.7(5) ?
    C1 C2 C3 . . 119.9(2) ?
    C1 C2 H2 . . 120.0 ?
    C3 C2 H2 . . 120.0 ?
    C4 C3 C2 . . 119.1(2) ?
    C4 C3 H3 . . 120.4 ?
    C2 C3 H3 . . 120.4 ?
    C5 C4 C3 . . 120.5(2) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 122.2(2) ?
    C4 C5 H5 . . 118.9 ?
    C6 C5 H5 . . 118.9 ?
    C1 C6 C5 . . 116.7(2) ?
    C1 C6 C7 . . 125.1(2) ?
    C5 C6 C7 . . 118.2(2) ?
    C6 C7 C8 . . 120.0(2) ?
    C6 C7 H7A . . 107.3 ?
    C8 C7 H7A . . 107.3 ?
    C6 C7 H7B . . 107.3 ?
    C8 C7 H7B . . 107.3 ?
    H7A C7 H7B . . 106.9 ?
    C9 C8 C7 . . 113.1(2) ?
    C9 C8 H8A . . 109.0 ?
    C7 C8 H8A . . 109.0 ?
    C9 C8 H8B . . 109.0 ?
    C7 C8 H8B . . 109.0 ?
    H8A C8 H8B . . 107.8 ?
    C14 C9 C10 . . 117.5(2) ?
    C14 C9 C8 . . 123.4(2) ?
    C10 C9 C8 . . 119.06(19) ?
    C11 C10 C9A . . 108.3(2) ?
    C11A C10 C9A . . 120.0 ?
    C11 C10 C9 . . 121.72(19) ?
    C11A C10 C9 . . 131.7(2) ?
    C11 C10 N1 . . 121.96(19) ?
    C11A C10 N1 . . 111.4(2) ?
    C9A C10 N1 . . 128.6(2) ?
    C9 C10 N1 . . 116.20(17) ?
    C10 C11A C12A . . 120.0 ?
    C10 C11A H11A . . 120.0 ?
    C12A C11A H11A . . 120.0 ?
    C13A C12A C11A . . 120.0 ?
    C13A C12A H12A . . 120.0 ?
    C11A C12A H12A . . 120.0 ?
    C12A C13A C14A . . 120.0 ?
    C12A C13A H13A . . 120.0 ?
    C14A C13A H13A . . 120.0 ?
    C13A C14A C9A . . 120.0 ?
    C13A C14A H14A . . 120.0 ?
    C9A C14A H14A . . 120.0 ?
    C14A C9A C10 . . 120.0 ?
    C14A C9A C8A . . 120.6(5) ?
    C10 C9A C8A . . 119.4(5) ?
    C8A C7A C6A . . 113.2(8) ?
    C8A C7A H7C . . 108.9 ?
    C6A C7A H7C . . 108.9 ?
    C8A C7A H7D . . 108.9 ?
    C6A C7A H7D . . 108.9 ?
    H7C C7A H7D . . 107.7 ?
    C9A C8A C7A . . 121.8(8) ?
    C9A C8A H8C . . 106.9 ?
    C7A C8A H8C . . 106.9 ?
    C9A C8A H8D . . 106.9 ?
    C7A C8A H8D . . 106.9 ?
    H8C C8A H8D . . 106.7 ?
    C10 C11 C12 . . 119.2(2) ?
    C10 C11 H11 . . 120.4 ?
    C12 C11 H11 . . 120.4 ?
    C13 C12 C11 . . 120.1(2) ?
    C13 C12 H12 . . 119.9 ?
    C11 C12 H12 . . 119.9 ?
    C12 C13 C14 . . 120.8(2) ?
    C12 C13 H13 . . 119.6 ?
    C14 C13 H13 . . 119.6 ?
    C13 C14 C9 . . 120.7(2) ?
    C13 C14 H14 . . 119.7 ?
    C9 C14 H14 . . 119.7 ?
    O2 S1 C16 . . 105.90(10) ?
    O2 S1 C17 . . 106.44(10) ?
    C16 S1 C17 . . 96.39(10) ?
    S1 C17 H17A . . 109.5 ?
    S1 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    S1 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    S1 C16 H16A . . 109.5 ?
    S1 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    S1 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 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
    C10 N1 C1 C2 . . . . -116.0(2) no
    C10 N1 C1 C6 . . . . 61.5(2) no
    C15 N1 C1 C2 . . . . 88.1(2) no
    C15 N1 C1 C6 . . . . -94.5(2) no
    C1 N1 C10 C9 . . . . -72.6(2) no
    C1 N1 C10 C11 . . . . 103.6(2) no
    C15 N1 C10 C9 . . . . 82.3(2) no
    C15 N1 C10 C11 . . . . -101.5(2) no
    C1 N1 C15 O1 . . . . -10.6(2) no
    C1 N1 C15 N2 . . . . 170.45(15) no
    C10 N1 C15 O1 . . . . -164.93(15) no
    C10 N1 C15 N2 . . . . 16.2(2) no
    N1 C1 C2 C3 . . . . 178.2(2) no
    C6 C1 C2 C3 . . . . 0.8(4) no
    N1 C1 C6 C5 . . . . -177.6(2) no
    N1 C1 C6 C7 . . . . 0.6(4) no
    C2 C1 C6 C5 . . . . -0.2(4) no
    C2 C1 C6 C7 . . . . 177.9(3) no
    C1 C2 C3 C4 . . . . -0.9(4) no
    C2 C3 C4 C5 . . . . 0.4(4) no
    C3 C4 C5 C6 . . . . 0.1(4) no
    C4 C5 C6 C1 . . . . -0.2(4) no
    C4 C5 C6 C7 . . . . -178.5(3) no
    C1 C6 C7 C8 . . . . -3.8(4) no
    C5 C6 C7 C8 . . . . 174.3(3) no
    C6 C7 C8 C9 . . . . -51.3(4) no
    C7 C8 C9 C10 . . . . 70.4(3) no
    C7 C8 C9 C14 . . . . -109.7(3) no
    C8 C9 C10 N1 . . . . -3.0(3) no
    C8 C9 C10 C11 . . . . -179.1(2) no
    C14 C9 C10 N1 . . . . 177.14(19) no
    C14 C9 C10 C11 . . . . 1.0(3) no
    C8 C9 C14 C13 . . . . 179.4(3) no
    C10 C9 C14 C13 . . . . -0.8(4) no
    N1 C10 C11 C12 . . . . -176.6(2) no
    C9 C10 C11 C12 . . . . -0.7(3) no
    C10 C11 C12 C13 . . . . 0.2(4) no
    C11 C12 C13 C14 . . . . 0.0(4) no
    C12 C13 C14 C9 . . . . 0.3(4) no
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
    N2 H2A O1 3_756 0.85(2) 2.05(2) 2.8977(19) 171(2) yes
    N2 H2B O2 . 0.82(2) 2.13(2) 2.885(2) 154(2) yes
    C16 H16C O1 1_455 0.9800 2.4500 3.294(2) 143.00 yes
