##############################################################################
#                                                                            #
# 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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2011-10-26
_journal_date_accepted     2011-10-26
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     11
_journal_page_first     o3127
_journal_page_last     o3127
_journal_paper_category     QO
_journal_coeditor_code     HG5127
_publ_contact_author
;
     Prof. Edward R.T. Tiekink
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     edward.tiekink@gmail.com
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
<i>N</i>'-(Adamantan-2-ylidene)thiophene-2-carbohydrazide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Kadi, Adnan A.' .
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
Riyadh
Saudi Arabia
;
    'Alanzi, Amer M.' .
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
Riyadh
Saudi Arabia
;
    'El-Emam, Ali A.'
;
Additional correspondence author, e-mail: elemam5@hotmail.com.
;
;
Department of Pharmaceutical Chemistry
College of Pharmacy
King Saud University
Riyadh
Saudi Arabia
;
    'Ng, Seik Weng' .
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
and Chemistry Department
Faculty of Science
King Abdulaziz University
PO Box 80203 Jeddah
Saudi Arabia
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
<i>N</i>'-(Adamantan-2-ylidene)thiophene-2-carbohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H18 N2 O S'
_chemical_formula_sum     'C15 H18 N2 O S'
_chemical_formula_iupac     'C15 H18 N2 O S'
_chemical_formula_weight     274.37
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
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'
    '-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     16.7262(2)
_cell_length_b     12.56630(10)
_cell_length_c     13.5562(2)
_cell_angle_alpha     90.00
_cell_angle_beta     102.4730(10)
_cell_angle_gamma     90.00
_cell_volume     2782.08(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     4116
_cell_measurement_theta_min     3.34
_cell_measurement_theta_max     76.29
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.310
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1168
_exptl_absorpt_coefficient_mu     2.007
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(CrysAlis PRO; Agilent, 2010)'
_exptl_absorpt_correction_T_min     0.5842
_exptl_absorpt_correction_T_max     0.6896
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_source     'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator     Mirror
_diffrn_measurement_device_type
                  'Agilent SuperNova Dual diffractometer with an Atlas detector'
_diffrn_measurement_method     '\w scan'
_diffrn_detector_area_resol_mean     10.4041
_diffrn_reflns_number     5687
_diffrn_reflns_av_R_equivalents     0.0151
_diffrn_reflns_av_sigmaI/netI     0.0199
_diffrn_reflns_theta_min     4.44
_diffrn_reflns_theta_max     76.49
_diffrn_reflns_theta_full     76.49
_diffrn_measured_fraction_theta_max     0.975
_diffrn_measured_fraction_theta_full     0.975
_diffrn_reflns_limit_h_min     -20
_diffrn_reflns_limit_h_max     21
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2849
_reflns_number_gt     2671
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0343
_refine_ls_R_factor_gt     0.0324
_refine_ls_wR_factor_gt     0.0854
_refine_ls_wR_factor_ref     0.0870
_refine_ls_goodness_of_fit_ref     1.036
_refine_ls_restrained_S_all     1.051
_refine_ls_number_reflns     2849
_refine_ls_number_parameters     189
_refine_ls_number_restraints     10
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0511P)^2^+1.8544P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.001
_refine_diff_density_max     0.375
_refine_diff_density_min     -0.391
_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' 0.0181 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'
_computing_data_collection     'CrysAlis PRO (Agilent, 2010)'
_computing_cell_refinement     'CrysAlis PRO (Agilent, 2010)'
_computing_data_reduction     'CrysAlis PRO (Agilent, 2010)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)
;
_computing_publication_material     '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_refinement_flags
    _atom_site_occupancy
    _atom_site_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.32529(2) 0.46310(4) 0.24150(3) 0.01360(14) Uani d PD 0.833(2) 1 A 1
    C C1 0.26341(15) 0.55387(19) 0.1659(2) 0.0172(5) Uani d PD 0.833(2) 1 A 1
    H H1A 0.2777 0.5884 0.1098 0.021 Uiso calc PR 0.833(2) 1 A 1
    C C2 0.1909(2) 0.5709(3) 0.1958(2) 0.0187(4) Uani d PD 0.833(2) 1 A 1
    H H2 0.1493 0.6191 0.1646 0.022 Uiso calc PR 0.833(2) 1 A 1
    C C3 0.18762(10) 0.5073(2) 0.2781(2) 0.0223(5) Uani d PD 0.833(2) 1 A 1
    H H3 0.1417 0.5081 0.3088 0.027 Uiso calc PR 0.833(2) 1 A 1
    S S1' 0.16790(19) 0.5096(3) 0.2790(2) 0.01360(14) Uani d PD 0.167(2) 1 A 2
    C C1' 0.2016(12) 0.5693(15) 0.1820(12) 0.0172(5) Uani d PD 0.167(2) 1 A 2
    H H1' 0.1703 0.6204 0.1384 0.021 Uiso calc PR 0.167(2) 1 A 2
    C C2' 0.2765(11) 0.5375(13) 0.1731(14) 0.0187(4) Uani d PD 0.167(2) 1 A 2
    H H2' 0.3044 0.5617 0.1234 0.022 Uiso calc PR 0.167(2) 1 A 2
    C C3' 0.3071(7) 0.4624(12) 0.2493(10) 0.0223(5) Uani d PD 0.167(2) 1 A 2
    H H3' 0.3588 0.4285 0.2565 0.027 Uiso calc PR 0.167(2) 1 A 2
    O O1 0.19394(5) 0.34953(7) 0.42862(7) 0.0180(2) Uani d . 1 1 . .
    N N1 0.32838(6) 0.32219(8) 0.44331(8) 0.0143(2) Uani d . 1 1 . .
    H H1 0.3254(10) 0.2681(13) 0.4887(12) 0.023(4) Uiso d . 1 1 . .
    N N2 0.39858(6) 0.33902(8) 0.40601(7) 0.0147(2) Uani d . 1 1 . .
    C C4 0.25352(7) 0.44346(9) 0.31283(8) 0.0135(2) Uani d D 1 1 . .
    C C5 0.25708(7) 0.36818(9) 0.39748(9) 0.0137(2) Uani d . 1 1 A .
    C C6 0.46677(7) 0.30469(9) 0.45855(9) 0.0137(2) Uani d . 1 1 . .
    C C7 0.54146(7) 0.31718(10) 0.41432(9) 0.0172(3) Uani d . 1 1 . .
    H H7 0.5274 0.3575 0.3493 0.021 Uiso calc R 1 1 . .
    C C8 0.57170(8) 0.20454(11) 0.39590(10) 0.0216(3) Uani d . 1 1 . .
    H H8A 0.5290 0.1666 0.3464 0.026 Uiso calc R 1 1 . .
    H H8B 0.6214 0.2095 0.3676 0.026 Uiso calc R 1 1 . .
    C C9 0.59118(7) 0.14246(10) 0.49565(10) 0.0194(3) Uani d . 1 1 . .
    H H9 0.6107 0.0694 0.4835 0.023 Uiso calc R 1 1 . .
    C C10 0.51402(7) 0.13459(10) 0.53943(10) 0.0195(3) Uani d . 1 1 . .
    H H10A 0.5265 0.0941 0.6035 0.023 Uiso calc R 1 1 . .
    H H10B 0.4706 0.0962 0.4914 0.023 Uiso calc R 1 1 . .
    C C11 0.48369(7) 0.24706(10) 0.55881(9) 0.0147(2) Uani d . 1 1 . .
    H H11 0.4329 0.2428 0.5862 0.018 Uiso calc R 1 1 . .
    C C12 0.55174(7) 0.30665(11) 0.63301(9) 0.0193(3) Uani d . 1 1 . .
    H H12A 0.5328 0.3792 0.6449 0.023 Uiso calc R 1 1 . .
    H H12B 0.5644 0.2687 0.6985 0.023 Uiso calc R 1 1 . .
    C C13 0.62905(7) 0.31363(10) 0.58972(9) 0.0177(3) Uani d . 1 1 . .
    H H13 0.6731 0.3514 0.6388 0.021 Uiso calc R 1 1 . .
    C C14 0.60877(7) 0.37598(10) 0.49038(10) 0.0196(3) Uani d . 1 1 . .
    H H14A 0.6585 0.3830 0.4623 0.024 Uiso calc R 1 1 . .
    H H14B 0.5897 0.4483 0.5028 0.024 Uiso calc R 1 1 . .
    C C15 0.65806(7) 0.20126(10) 0.57098(9) 0.0184(3) Uani d . 1 1 . .
    H H15A 0.6712 0.1615 0.6355 0.022 Uiso calc R 1 1 . .
    H H15B 0.7084 0.2056 0.5439 0.022 Uiso calc R 1 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
    S1 0.0146(3) 0.0164(2) 0.0113(2) -0.00024(18) 0.00607(15) 0.00223(12)
    C1 0.0211(13) 0.0172(11) 0.0118(8) 0.0019(8) 0.0004(8) 0.0070(7)
    C2 0.0190(12) 0.0181(7) 0.0184(12) 0.0026(7) 0.0026(6) 0.0013(8)
    C3 0.0147(11) 0.0256(8) 0.0287(8) -0.0040(10) 0.0096(9) -0.0030(7)
    S1' 0.0146(3) 0.0164(2) 0.0113(2) -0.00024(18) 0.00607(15) 0.00223(12)
    C1' 0.0211(13) 0.0172(11) 0.0118(8) 0.0019(8) 0.0004(8) 0.0070(7)
    C2' 0.0190(12) 0.0181(7) 0.0184(12) 0.0026(7) 0.0026(6) 0.0013(8)
    C3' 0.0147(11) 0.0256(8) 0.0287(8) -0.0040(10) 0.0096(9) -0.0030(7)
    O1 0.0134(4) 0.0194(4) 0.0217(4) 0.0002(3) 0.0053(3) 0.0062(3)
    N1 0.0125(5) 0.0153(5) 0.0153(5) 0.0001(4) 0.0036(4) 0.0035(4)
    N2 0.0139(5) 0.0153(5) 0.0159(5) 0.0005(4) 0.0052(4) 0.0016(4)
    C4 0.0149(5) 0.0128(5) 0.0125(5) -0.0014(4) 0.0024(4) -0.0010(4)
    C5 0.0141(5) 0.0118(5) 0.0147(5) -0.0010(4) 0.0021(4) -0.0015(4)
    C6 0.0149(5) 0.0128(5) 0.0138(5) 0.0000(4) 0.0041(4) 0.0006(4)
    C7 0.0160(6) 0.0213(6) 0.0160(6) 0.0026(4) 0.0068(4) 0.0059(5)
    C8 0.0214(6) 0.0266(7) 0.0176(6) 0.0041(5) 0.0062(5) -0.0034(5)
    C9 0.0187(6) 0.0145(6) 0.0249(6) 0.0031(4) 0.0045(5) 0.0001(5)
    C10 0.0167(6) 0.0152(6) 0.0251(6) -0.0025(4) 0.0009(5) 0.0059(5)
    C11 0.0115(5) 0.0189(6) 0.0141(5) -0.0009(4) 0.0035(4) 0.0040(4)
    C12 0.0155(6) 0.0274(7) 0.0148(6) -0.0014(5) 0.0029(5) -0.0027(5)
    C13 0.0130(5) 0.0202(6) 0.0196(6) -0.0035(4) 0.0028(4) -0.0011(5)
    C14 0.0153(5) 0.0161(6) 0.0289(7) -0.0009(4) 0.0081(5) 0.0051(5)
    C15 0.0132(5) 0.0204(6) 0.0215(6) 0.0012(4) 0.0037(5) 0.0060(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 C4 . 1.7142(12) ?
    S1 C1 . 1.7215(15) ?
    C1 C2 . 1.377(2) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.382(3) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.362(2) ?
    C3 H3 . 0.9500 ?
    S1' C4 . 1.634(3) ?
    S1' C1' . 1.712(9) ?
    C1' C2' . 1.344(9) ?
    C1' H1' . 0.9500 ?
    C2' C3' . 1.411(10) ?
    C2' H2' . 0.9500 ?
    C3' C4 . 1.391(8) ?
    C3' H3' . 0.9500 ?
    O1 C5 . 1.2414(14) ?
    N1 C5 . 1.3499(15) ?
    N1 N2 . 1.3912(13) ?
    N1 H1 . 0.926(17) ?
    N2 C6 . 1.2820(15) ?
    C4 C5 . 1.4784(16) ?
    C6 C7 . 1.5062(15) ?
    C6 C11 . 1.5118(15) ?
    C7 C8 . 1.5415(18) ?
    C7 C14 . 1.5412(17) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.5340(18) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C15 . 1.5319(17) ?
    C9 C10 . 1.5358(17) ?
    C9 H9 . 1.0000 ?
    C10 C11 . 1.5432(17) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.5406(16) ?
    C11 H11 . 1.0000 ?
    C12 C13 . 1.5336(16) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.5313(17) ?
    C13 C15 . 1.5321(17) ?
    C13 H13 . 1.0000 ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
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
    C4 S1 C1 . . 91.53(11) ?
    C2 C1 S1 . . 112.5(3) ?
    C2 C1 H1A . . 123.7 ?
    S1 C1 H1A . . 123.7 ?
    C1 C2 C3 . . 109.8(3) ?
    C1 C2 H2 . . 125.1 ?
    C3 C2 H2 . . 125.1 ?
    C4 C3 C2 . . 116.73(19) ?
    C4 C3 H3 . . 121.6 ?
    C2 C3 H3 . . 121.6 ?
    C4 S1' C1' . . 91.4(7) ?
    C2' C1' S1' . . 114.0(15) ?
    C2' C1' H1' . . 123.0 ?
    S1' C1' H1' . . 123.0 ?
    C1' C2' C3' . . 109.4(17) ?
    C1' C2' H2' . . 125.3 ?
    C3' C2' H2' . . 125.3 ?
    C4 C3' C2' . . 112.8(12) ?
    C4 C3' H3' . . 123.6 ?
    C2' C3' H3' . . 123.6 ?
    C5 N1 N2 . . 119.91(10) ?
    C5 N1 H1 . . 116.8(10) ?
    N2 N1 H1 . . 121.6(10) ?
    C6 N2 N1 . . 117.79(10) ?
    C3 C4 C3' . . 105.5(6) ?
    C3 C4 C5 . . 122.63(13) ?
    C3' C4 C5 . . 131.8(6) ?
    C3' C4 S1' . . 112.5(6) ?
    C5 C4 S1' . . 115.42(13) ?
    C3 C4 S1 . . 109.44(12) ?
    C5 C4 S1 . . 127.90(9) ?
    S1' C4 S1 . . 116.54(13) ?
    O1 C5 N1 . . 119.64(10) ?
    O1 C5 C4 . . 119.35(10) ?
    N1 C5 C4 . . 120.98(10) ?
    N2 C6 C7 . . 117.30(10) ?
    N2 C6 C11 . . 129.20(11) ?
    C7 C6 C11 . . 113.42(9) ?
    C6 C7 C8 . . 107.35(10) ?
    C6 C7 C14 . . 109.42(10) ?
    C8 C7 C14 . . 109.31(10) ?
    C6 C7 H7 . . 110.2 ?
    C8 C7 H7 . . 110.2 ?
    C14 C7 H7 . . 110.2 ?
    C9 C8 C7 . . 109.81(10) ?
    C9 C8 H8A . . 109.7 ?
    C7 C8 H8A . . 109.7 ?
    C9 C8 H8B . . 109.7 ?
    C7 C8 H8B . . 109.7 ?
    H8A C8 H8B . . 108.2 ?
    C15 C9 C8 . . 109.14(10) ?
    C15 C9 C10 . . 109.09(10) ?
    C8 C9 C10 . . 109.70(10) ?
    C15 C9 H9 . . 109.6 ?
    C8 C9 H9 . . 109.6 ?
    C10 C9 H9 . . 109.6 ?
    C9 C10 C11 . . 109.97(10) ?
    C9 C10 H10A . . 109.7 ?
    C11 C10 H10A . . 109.7 ?
    C9 C10 H10B . . 109.7 ?
    C11 C10 H10B . . 109.7 ?
    H10A C10 H10B . . 108.2 ?
    C6 C11 C12 . . 108.82(10) ?
    C6 C11 C10 . . 106.87(10) ?
    C12 C11 C10 . . 109.43(10) ?
    C6 C11 H11 . . 110.5 ?
    C12 C11 H11 . . 110.5 ?
    C10 C11 H11 . . 110.5 ?
    C13 C12 C11 . . 110.07(10) ?
    C13 C12 H12A . . 109.6 ?
    C11 C12 H12A . . 109.6 ?
    C13 C12 H12B . . 109.6 ?
    C11 C12 H12B . . 109.6 ?
    H12A C12 H12B . . 108.2 ?
    C14 C13 C15 . . 110.10(10) ?
    C14 C13 C12 . . 108.72(10) ?
    C15 C13 C12 . . 109.52(10) ?
    C14 C13 H13 . . 109.5 ?
    C15 C13 H13 . . 109.5 ?
    C12 C13 H13 . . 109.5 ?
    C13 C14 C7 . . 109.52(10) ?
    C13 C14 H14A . . 109.8 ?
    C7 C14 H14A . . 109.8 ?
    C13 C14 H14B . . 109.8 ?
    C7 C14 H14B . . 109.8 ?
    H14A C14 H14B . . 108.2 ?
    C13 C15 C9 . . 110.08(10) ?
    C13 C15 H15A . . 109.6 ?
    C9 C15 H15A . . 109.6 ?
    C13 C15 H15B . . 109.6 ?
    C9 C15 H15B . . 109.6 ?
    H15A C15 H15B . . 108.2 ?
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
    C4 S1 C1 C2 . . . . 1.5(2) ?
    S1 C1 C2 C3 . . . . -1.4(3) ?
    C1 C2 C3 C4 . . . . 0.4(4) ?
    C4 S1' C1' C2' . . . . 1.7(16) ?
    S1' C1' C2' C3' . . . . -1(2) ?
    C1' C2' C3' C4 . . . . -1(2) ?
    C5 N1 N2 C6 . . . . 171.74(11) ?
    C2 C3 C4 C3' . . . . -0.8(7) ?
    C2 C3 C4 C5 . . . . -177.5(2) ?
    C2 C3 C4 S1' . . . . -161(2) ?
    C2 C3 C4 S1 . . . . 0.8(3) ?
    C2' C3' C4 C3 . . . . -0.4(14) ?
    C2' C3' C4 C5 . . . . 175.8(10) ?
    C2' C3' C4 S1' . . . . 2.4(16) ?
    C2' C3' C4 S1 . . . . -160(10) ?
    C1' S1' C4 C3 . . . . 18.8(18) ?
    C1' S1' C4 C3' . . . . -2.3(11) ?
    C1' S1' C4 C5 . . . . -176.8(7) ?
    C1' S1' C4 S1 . . . . -0.8(7) ?
    C1 S1 C4 C3 . . . . -1.28(18) ?
    C1 S1 C4 C3' . . . . 19(9) ?
    C1 S1 C4 C5 . . . . 176.83(14) ?
    C1 S1 C4 S1' . . . . 1.40(18) ?
    N2 N1 C5 O1 . . . . 177.15(10) ?
    N2 N1 C5 C4 . . . . -4.97(16) ?
    C3 C4 C5 O1 . . . . 11.4(2) ?
    C3' C4 C5 O1 . . . . -164.3(9) ?
    S1' C4 C5 O1 . . . . 9.0(2) ?
    S1 C4 C5 O1 . . . . -166.49(9) ?
    C3 C4 C5 N1 . . . . -166.50(17) ?
    C3' C4 C5 N1 . . . . 17.8(9) ?
    S1' C4 C5 N1 . . . . -168.90(17) ?
    S1 C4 C5 N1 . . . . 15.62(17) ?
    N1 N2 C6 C7 . . . . 176.23(10) ?
    N1 N2 C6 C11 . . . . -0.37(18) ?
    N2 C6 C7 C8 . . . . -115.56(12) ?
    C11 C6 C7 C8 . . . . 61.57(13) ?
    N2 C6 C7 C14 . . . . 125.92(11) ?
    C11 C6 C7 C14 . . . . -56.95(13) ?
    C6 C7 C8 C9 . . . . -58.56(13) ?
    C14 C7 C8 C9 . . . . 60.04(13) ?
    C7 C8 C9 C15 . . . . -60.03(13) ?
    C7 C8 C9 C10 . . . . 59.45(13) ?
    C15 C9 C10 C11 . . . . 59.76(12) ?
    C8 C9 C10 C11 . . . . -59.75(13) ?
    N2 C6 C11 C12 . . . . -126.71(13) ?
    C7 C6 C11 C12 . . . . 56.58(13) ?
    N2 C6 C11 C10 . . . . 115.21(13) ?
    C7 C6 C11 C10 . . . . -61.49(12) ?
    C9 C10 C11 C6 . . . . 58.68(12) ?
    C9 C10 C11 C12 . . . . -58.99(13) ?
    C6 C11 C12 C13 . . . . -57.90(13) ?
    C10 C11 C12 C13 . . . . 58.55(13) ?
    C11 C12 C13 C14 . . . . 61.27(13) ?
    C11 C12 C13 C15 . . . . -59.07(13) ?
    C15 C13 C14 C7 . . . . 59.00(12) ?
    C12 C13 C14 C7 . . . . -60.97(13) ?
    C6 C7 C14 C13 . . . . 58.13(13) ?
    C8 C7 C14 C13 . . . . -59.16(13) ?
    C14 C13 C15 C9 . . . . -59.43(12) ?
    C12 C13 C15 C9 . . . . 60.06(13) ?
    C8 C9 C15 C13 . . . . 59.55(13) ?
    C10 C9 C15 C13 . . . . -60.30(13) ?
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
    N1 H1 O1 7_556 0.93(2) 1.92(2) 2.8440(10)
                                            173(2) yes
    C13 H13 Cg1 4_666 1.00 2.61 3.5791(16) 163 yes
    C15 H15a Cg1 8_556 0.99 2.69 3.5683(16) 148 yes