##############################################################################
#                                                                            #
# 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
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2013-12-19
_journal_date_accepted     2014-01-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2014
_journal_volume     70
_journal_issue      3
_journal_page_first     o288
_journal_page_last     o288
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536814001986
_journal_coeditor_code     HB7176
_publ_contact_author_name     'Ibrahim Abdul Razak'
_publ_contact_author_address
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
_publ_contact_author_email     'arazaki@usm.my'
_publ_contact_author_fax     '+6046539150'
_publ_contact_author_phone     '+6046535306'
_publ_section_title
;
9-Benzyl-6-benzylsulfanyl-9<i>H</i>-purin-2-amine
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hariono, Maywan' .
;
Pharmaceutical Design and Simulation (PhDs) Laboratory,
School of Pharmaceutical Sciences,
Universiti Sains Malaysia,
11800 Minden,
Pulau Pinang,
Malaysia
;
    'Wahab, Habibah A.'
;
Additional correspondence author, e-mail: habibahw@usm.my.
;
;
Pharmaceutical Design and Simulation (PhDs) Laboratory,
School of Pharmaceutical Sciences,
Universiti Sains Malaysia,
11800 Minden,
Pulau Pinang,
Malaysia
Malaysian Institute of Pharmaceuticals and Nutraceuticals,
Ministry of Science Technology and Inovation,
11700 Halaman Bukit Gambir,
Pulau Pinang,
Malaysia
;
    'Tan, Mei Lan' .
;
Malaysian Institute of Pharmaceuticals and Nutraceuticals,
Ministry of Science Technology and Inovation,
11700 Halaman Bukit Gambir,
Pulau Pinang,
Malaysia
;
    'Rosli, Mohd Mustaqim' .
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
    'Razak, Ibrahim Abdul'
;
Thomson Reuters ResearcherID: A-5599-2009.
;
;
X-ray Crystallography Unit
School of Physics
Universiti Sains Malaysia
11800 USM
Penang
Malaysia
;
_database_code_depnum_ccdc_archive     'CCDC 983914'
_chemical_name_systematic
;
9-Benzyl-6-benzylsulfanyl-9<i>H</i>-purin-2-amine
;
_chemical_name_common
;
;
_chemical_formula_moiety     'C19 H17 N5 S'
_chemical_formula_sum     'C19 H17 N5 S'
_chemical_formula_iupac     'C19 H17 N5 S'
_chemical_formula_weight     347.44
_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, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     16.7346(7)
_cell_length_b     5.5511(3)
_cell_length_c     20.4817(10)
_cell_angle_alpha     90.00
_cell_angle_beta     121.325(3)
_cell_angle_gamma     90.00
_cell_volume     1625.31(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3425
_cell_measurement_theta_min     2.33
_cell_measurement_theta_max     30.02
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.69
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     1.420
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     728
_exptl_absorpt_coefficient_mu     0.211
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(<i>SADABS</i>; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.8684
_exptl_absorpt_correction_T_max     0.9718
_exptl_special_details     .
_diffrn_ambient_temperature     100
_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     'Bruker SMART APEXII CCD'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16728
_diffrn_reflns_av_R_equivalents     0.0479
_diffrn_reflns_av_sigmaI/netI     0.0609
_diffrn_reflns_theta_min     2.00
_diffrn_reflns_theta_max     30.60
_diffrn_reflns_theta_full     30.60
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -25
_diffrn_reflns_limit_l_max     29
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     4956
_reflns_number_gt     3416
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0802
_refine_ls_R_factor_gt     0.0501
_refine_ls_wR_factor_gt     0.1163
_refine_ls_wR_factor_ref     0.1374
_refine_ls_goodness_of_fit_ref     1.060
_refine_ls_restrained_S_all     1.060
_refine_ls_number_reflns     4956
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[\s^2^(Fo^2^)+(0.0602P)^2^+0.4349P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.327
_refine_diff_density_min     -0.577
_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'
    '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, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
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 0.24764(3) 0.72454(8) 0.12637(3) 0.01824(13) Uani d . 1 1 . .
    N N1 0.52964(10) 1.0733(3) 0.14394(8) 0.0147(3) Uani d . 1 1 . .
    N N2 0.42255(10) 1.0996(3) 0.17932(8) 0.0169(3) Uani d . 1 1 . .
    N N3 0.47003(10) 0.7208(3) 0.06126(8) 0.0148(3) Uani d . 1 1 . .
    N N4 0.32973(10) 0.5624(3) 0.05291(8) 0.0151(3) Uani d . 1 1 . .
    N N5 0.39014(11) 0.3896(3) -0.01293(9) 0.0183(3) Uani d . 1 1 . .
    C C1 0.70179(12) 0.7950(3) 0.20967(10) 0.0170(4) Uani d . 1 1 . .
    H H1A 0.6619 0.7724 0.2293 0.020 Uiso calc R 1 1 . .
    C C2 0.77591(13) 0.6376(3) 0.23027(10) 0.0200(4) Uani d . 1 1 . .
    H H2A 0.7865 0.5080 0.2642 0.024 Uiso calc R 1 1 . .
    C C3 0.83454(13) 0.6682(4) 0.20170(10) 0.0211(4) Uani d . 1 1 . .
    H H3A 0.8838 0.5570 0.2147 0.025 Uiso calc R 1 1 . .
    C C4 0.82082(13) 0.8621(3) 0.15408(10) 0.0210(4) Uani d . 1 1 . .
    H H4A 0.8617 0.8863 0.1355 0.025 Uiso calc R 1 1 . .
    C C5 0.74731(12) 1.0206(3) 0.13374(10) 0.0190(4) Uani d . 1 1 . .
    H H5A 0.7385 1.1538 0.1016 0.023 Uiso calc R 1 1 . .
    C C6 0.68604(12) 0.9858(3) 0.16023(9) 0.0154(3) Uani d . 1 1 . .
    C C7 0.60378(12) 1.1554(3) 0.13203(10) 0.0176(4) Uani d . 1 1 . .
    H H7A 0.6271 1.3124 0.1581 0.021 Uiso calc R 1 1 . .
    H H7B 0.5767 1.1826 0.0767 0.021 Uiso calc R 1 1 . .
    C C8 0.49754(13) 1.1938(3) 0.18504(10) 0.0165(4) Uani d . 1 1 . .
    H H8A 0.5274 1.3330 0.2149 0.020 Uiso calc R 1 1 . .
    C C9 0.46824(11) 0.8869(3) 0.10795(9) 0.0133(3) Uani d . 1 1 . .
    C C10 0.39805(12) 0.5647(3) 0.03571(9) 0.0144(3) Uani d . 1 1 . .
    C C11 0.33280(12) 0.7292(3) 0.10083(9) 0.0138(3) Uani d . 1 1 . .
    C C12 0.40253(12) 0.9046(3) 0.13023(9) 0.0141(3) Uani d . 1 1 . .
    C C13 0.19169(13) 0.4383(3) 0.08654(10) 0.0186(4) Uani d . 1 1 . .
    H H13A 0.2409 0.3215 0.0950 0.022 Uiso calc R 1 1 . .
    H H13B 0.1636 0.3806 0.1160 0.022 Uiso calc R 1 1 . .
    C C14 0.11669(12) 0.4322(3) 0.00268(10) 0.0166(4) Uani d . 1 1 . .
    C C15 0.10259(13) 0.6128(3) -0.04927(10) 0.0198(4) Uani d . 1 1 . .
    H H15A 0.1421 0.7504 -0.0327 0.024 Uiso calc R 1 1 . .
    C C16 0.03108(13) 0.5934(3) -0.12532(11) 0.0221(4) Uani d . 1 1 . .
    H H16A 0.0219 0.7190 -0.1601 0.027 Uiso calc R 1 1 . .
    C C17 -0.02712(13) 0.3932(3) -0.15127(11) 0.0217(4) Uani d . 1 1 . .
    H H17A -0.0761 0.3812 -0.2033 0.026 Uiso calc R 1 1 . .
    C C18 -0.01235(13) 0.2113(3) -0.09980(11) 0.0217(4) Uani d . 1 1 . .
    H H18A -0.0512 0.0726 -0.1168 0.026 Uiso calc R 1 1 . .
    C C19 0.05850(13) 0.2296(3) -0.02383(11) 0.0196(4) Uani d . 1 1 . .
    H H19A 0.0677 0.1032 0.0107 0.023 Uiso calc R 1 1 . .
    H H1N5 0.4310(15) 0.370(4) -0.0289(12) 0.030(6) Uiso d . 1 1 . .
    H H2N5 0.3390(15) 0.304(4) -0.0358(12) 0.024(6) Uiso d . 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 0.0183(2) 0.0203(2) 0.0209(2) -0.00120(18) 0.0136(2) -0.00239(18)
    N1 0.0136(7) 0.0158(7) 0.0139(7) -0.0025(6) 0.0066(6) -0.0020(6)
    N2 0.0205(8) 0.0153(7) 0.0157(7) 0.0009(6) 0.0100(6) -0.0001(6)
    N3 0.0160(7) 0.0152(7) 0.0150(7) -0.0017(6) 0.0095(6) -0.0013(6)
    N4 0.0148(7) 0.0163(7) 0.0158(7) 0.0013(6) 0.0090(6) -0.0001(6)
    N5 0.0161(8) 0.0203(8) 0.0209(8) -0.0053(7) 0.0113(7) -0.0083(6)
    C1 0.0161(9) 0.0189(9) 0.0148(8) -0.0039(7) 0.0072(7) -0.0020(7)
    C2 0.0188(9) 0.0186(9) 0.0177(9) -0.0028(7) 0.0061(7) -0.0005(7)
    C3 0.0174(9) 0.0218(9) 0.0200(9) 0.0004(7) 0.0067(8) -0.0035(7)
    C4 0.0183(9) 0.0238(10) 0.0231(9) -0.0039(8) 0.0121(8) -0.0046(8)
    C5 0.0203(9) 0.0188(9) 0.0176(8) -0.0052(7) 0.0097(8) -0.0025(7)
    C6 0.0151(9) 0.0153(8) 0.0140(8) -0.0039(7) 0.0062(7) -0.0047(6)
    C7 0.0180(9) 0.0156(8) 0.0214(9) -0.0016(7) 0.0117(8) 0.0005(7)
    C8 0.0214(9) 0.0140(8) 0.0140(8) -0.0004(7) 0.0092(7) -0.0013(6)
    C9 0.0140(8) 0.0134(8) 0.0107(7) 0.0003(6) 0.0051(6) 0.0004(6)
    C10 0.0148(8) 0.0141(8) 0.0142(8) 0.0004(7) 0.0074(7) 0.0006(6)
    C11 0.0134(8) 0.0149(8) 0.0129(8) 0.0017(6) 0.0066(7) 0.0026(6)
    C12 0.0165(8) 0.0131(8) 0.0139(8) 0.0007(7) 0.0088(7) 0.0002(6)
    C13 0.0196(9) 0.0171(9) 0.0222(9) -0.0022(7) 0.0129(8) 0.0012(7)
    C14 0.0133(8) 0.0187(9) 0.0196(8) -0.0001(7) 0.0099(7) -0.0001(7)
    C15 0.0189(9) 0.0178(9) 0.0241(9) 0.0003(7) 0.0122(8) 0.0008(7)
    C16 0.0227(10) 0.0212(9) 0.0225(9) 0.0048(8) 0.0118(8) 0.0056(8)
    C17 0.0168(9) 0.0252(10) 0.0194(9) 0.0033(8) 0.0068(7) 0.0007(8)
    C18 0.0180(9) 0.0203(9) 0.0268(10) -0.0015(7) 0.0117(8) -0.0013(8)
    C19 0.0184(9) 0.0187(9) 0.0235(9) 0.0003(7) 0.0122(8) 0.0017(7)
_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
    S1 C11 . 1.7551(17) ?
    S1 C13 . 1.8091(18) ?
    N1 C9 . 1.372(2) ?
    N1 C8 . 1.384(2) ?
    N1 C7 . 1.456(2) ?
    N2 C8 . 1.307(2) ?
    N2 C12 . 1.395(2) ?
    N3 C9 . 1.340(2) ?
    N3 C10 . 1.349(2) ?
    N4 C11 . 1.331(2) ?
    N4 C10 . 1.360(2) ?
    N5 C10 . 1.348(2) ?
    N5 H1N5 . 0.90(2) ?
    N5 H2N5 . 0.87(2) ?
    C1 C2 . 1.392(2) ?
    C1 C6 . 1.392(2) ?
    C1 H1A . 0.9500 ?
    C2 C3 . 1.390(3) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.389(3) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.388(3) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.400(2) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.513(2) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 H8A . 0.9500 ?
    C9 C12 . 1.396(2) ?
    C11 C12 . 1.393(2) ?
    C13 C14 . 1.512(2) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.390(2) ?
    C14 C19 . 1.399(2) ?
    C15 C16 . 1.390(3) ?
    C15 H15A . 0.9500 ?
    C16 C17 . 1.388(3) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.386(3) ?
    C17 H17A . 0.9500 ?
    C18 C19 . 1.385(3) ?
    C18 H18A . 0.9500 ?
    C19 H19A . 0.9500 ?
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
    C11 S1 C13 . . 100.87(8) ?
    C9 N1 C8 . . 105.78(14) ?
    C9 N1 C7 . . 127.68(14) ?
    C8 N1 C7 . . 125.79(14) ?
    C8 N2 C12 . . 103.57(14) ?
    C9 N3 C10 . . 111.85(14) ?
    C11 N4 C10 . . 117.98(14) ?
    C10 N5 H1N5 . . 123.6(14) ?
    C10 N5 H2N5 . . 118.7(14) ?
    H1N5 N5 H2N5 . . 117.1(19) ?
    C2 C1 C6 . . 120.00(16) ?
    C2 C1 H1A . . 120.0 ?
    C6 C1 H1A . . 120.0 ?
    C3 C2 C1 . . 120.58(17) ?
    C3 C2 H2A . . 119.7 ?
    C1 C2 H2A . . 119.7 ?
    C4 C3 C2 . . 119.68(18) ?
    C4 C3 H3A . . 120.2 ?
    C2 C3 H3A . . 120.2 ?
    C5 C4 C3 . . 119.92(17) ?
    C5 C4 H4A . . 120.0 ?
    C3 C4 H4A . . 120.0 ?
    C4 C5 C6 . . 120.63(17) ?
    C4 C5 H5A . . 119.7 ?
    C6 C5 H5A . . 119.7 ?
    C1 C6 C5 . . 119.13(16) ?
    C1 C6 C7 . . 122.79(15) ?
    C5 C6 C7 . . 118.07(15) ?
    N1 C7 C6 . . 115.28(14) ?
    N1 C7 H7A . . 108.5 ?
    C6 C7 H7A . . 108.5 ?
    N1 C7 H7B . . 108.5 ?
    C6 C7 H7B . . 108.5 ?
    H7A C7 H7B . . 107.5 ?
    N2 C8 N1 . . 114.24(15) ?
    N2 C8 H8A . . 122.9 ?
    N1 C8 H8A . . 122.9 ?
    N3 C9 N1 . . 127.88(15) ?
    N3 C9 C12 . . 126.53(15) ?
    N1 C9 C12 . . 105.59(14) ?
    N5 C10 N3 . . 118.33(15) ?
    N5 C10 N4 . . 114.32(15) ?
    N3 C10 N4 . . 127.34(15) ?
    N4 C11 C12 . . 120.50(15) ?
    N4 C11 S1 . . 118.92(13) ?
    C12 C11 S1 . . 120.58(13) ?
    C11 C12 N2 . . 133.42(15) ?
    C11 C12 C9 . . 115.76(15) ?
    N2 C12 C9 . . 110.81(15) ?
    C14 C13 S1 . . 117.49(13) ?
    C14 C13 H13A . . 107.9 ?
    S1 C13 H13A . . 107.9 ?
    C14 C13 H13B . . 107.9 ?
    S1 C13 H13B . . 107.9 ?
    H13A C13 H13B . . 107.2 ?
    C15 C14 C19 . . 118.40(17) ?
    C15 C14 C13 . . 124.32(16) ?
    C19 C14 C13 . . 117.28(16) ?
    C16 C15 C14 . . 120.45(17) ?
    C16 C15 H15A . . 119.8 ?
    C14 C15 H15A . . 119.8 ?
    C17 C16 C15 . . 120.97(17) ?
    C17 C16 H16A . . 119.5 ?
    C15 C16 H16A . . 119.5 ?
    C18 C17 C16 . . 118.67(17) ?
    C18 C17 H17A . . 120.7 ?
    C16 C17 H17A . . 120.7 ?
    C19 C18 C17 . . 120.73(18) ?
    C19 C18 H18A . . 119.6 ?
    C17 C18 H18A . . 119.6 ?
    C18 C19 C14 . . 120.75(17) ?
    C18 C19 H19A . . 119.6 ?
    C14 C19 H19A . . 119.6 ?
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
    C6 C1 C2 C3 . . . . -0.2(3) ?
    C1 C2 C3 C4 . . . . 2.1(3) ?
    C2 C3 C4 C5 . . . . -1.6(3) ?
    C3 C4 C5 C6 . . . . -0.6(3) ?
    C2 C1 C6 C5 . . . . -2.0(2) ?
    C2 C1 C6 C7 . . . . 176.53(16) ?
    C4 C5 C6 C1 . . . . 2.4(2) ?
    C4 C5 C6 C7 . . . . -176.18(16) ?
    C9 N1 C7 C6 . . . . -69.9(2) ?
    C8 N1 C7 C6 . . . . 121.46(18) ?
    C1 C6 C7 N1 . . . . -14.7(2) ?
    C5 C6 C7 N1 . . . . 163.78(15) ?
    C12 N2 C8 N1 . . . . -0.76(19) ?
    C9 N1 C8 N2 . . . . 0.87(19) ?
    C7 N1 C8 N2 . . . . 171.58(15) ?
    C10 N3 C9 N1 . . . . -179.61(16) ?
    C10 N3 C9 C12 . . . . 0.6(2) ?
    C8 N1 C9 N3 . . . . 179.63(17) ?
    C7 N1 C9 N3 . . . . 9.2(3) ?
    C8 N1 C9 C12 . . . . -0.55(17) ?
    C7 N1 C9 C12 . . . . -171.03(16) ?
    C9 N3 C10 N5 . . . . 178.94(15) ?
    C9 N3 C10 N4 . . . . -0.5(2) ?
    C11 N4 C10 N5 . . . . 179.75(15) ?
    C11 N4 C10 N3 . . . . -0.8(3) ?
    C10 N4 C11 C12 . . . . 2.0(2) ?
    C10 N4 C11 S1 . . . . -178.00(12) ?
    C13 S1 C11 N4 . . . . 9.65(15) ?
    C13 S1 C11 C12 . . . . -170.34(14) ?
    N4 C11 C12 N2 . . . . 178.87(17) ?
    S1 C11 C12 N2 . . . . -1.1(3) ?
    N4 C11 C12 C9 . . . . -1.9(2) ?
    S1 C11 C12 C9 . . . . 178.12(12) ?
    C8 N2 C12 C11 . . . . 179.67(19) ?
    C8 N2 C12 C9 . . . . 0.37(18) ?
    N3 C9 C12 C11 . . . . 0.5(3) ?
    N1 C9 C12 C11 . . . . -179.30(14) ?
    N3 C9 C12 N2 . . . . 179.94(15) ?
    N1 C9 C12 N2 . . . . 0.13(18) ?
    C11 S1 C13 C14 . . . . -83.26(14) ?
    S1 C13 C14 C15 . . . . 15.4(2) ?
    S1 C13 C14 C19 . . . . -165.09(13) ?
    C19 C14 C15 C16 . . . . 1.2(3) ?
    C13 C14 C15 C16 . . . . -179.25(16) ?
    C14 C15 C16 C17 . . . . -0.6(3) ?
    C15 C16 C17 C18 . . . . -0.3(3) ?
    C16 C17 C18 C19 . . . . 0.6(3) ?
    C17 C18 C19 C14 . . . . 0.0(3) ?
    C15 C14 C19 C18 . . . . -0.9(3) ?
    C13 C14 C19 C18 . . . . 179.50(16) ?
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
    N5 H1N5 N3 3_665 0.91(3) 2.14(3) 3.040(3) 173(2) yes
    C7 H7B N3 3_675 0.99 2.57 3.548(2) 172 yes
    C8 H8A N2 2_655 0.95 2.39 3.274(2) 155 yes
_iucr_refine_instructions_details
;
TITL mh010_0m in P2(1)/c (100K)
CELL  0.71073   16.7346    5.5511   20.4817    90.000   121.325    90.000
ZERR  4           0.0007    0.0003    0.0010     0.000     0.003     0.000
LATT   1
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SFAC C H N S
UNIT 76 68 20 4
TEMP -173.000
SIZE 0.136 0.191 0.687
L.S. 10
BOND $H
FMAP 2 2 60
PLAN 20
ACTA
CONF
WGHT      0.0602      0.4349
FVAR       0.59395
S1    4    0.247645    0.724543    0.126370    11.00000    0.01831    0.02031 =
         0.02092   -0.00239    0.01358   -0.00120
N1    3    0.529643    1.073328    0.143937    11.00000    0.01357    0.01578 =
         0.01390   -0.00204    0.00660   -0.00251
N2    3    0.422546    1.099638    0.179316    11.00000    0.02049    0.01533 =
         0.01573   -0.00010    0.01004    0.00086
N3    3    0.470028    0.720797    0.061259    11.00000    0.01603    0.01520 =
         0.01503   -0.00130    0.00947   -0.00169
N4    3    0.329725    0.562408    0.052909    11.00000    0.01477    0.01627 =
         0.01576   -0.00009    0.00896    0.00126
N5    3    0.390141    0.389574   -0.012930    11.00000    0.01612    0.02026 =
         0.02089   -0.00826    0.01135   -0.00525
C1    1    0.701793    0.795032    0.209670    11.00000    0.01608    0.01888 =
         0.01482   -0.00203    0.00716   -0.00392
AFIX  43
H1A   2    0.661935    0.772372    0.229341    11.00000   -1.20000
AFIX   0
C2    1    0.775913    0.637578    0.230268    11.00000    0.01883    0.01863 =
         0.01766   -0.00052    0.00610   -0.00280
AFIX  43
H2A   2    0.786525    0.508024    0.264163    11.00000   -1.20000
AFIX   0
C3    1    0.834542    0.668164    0.201697    11.00000    0.01736    0.02180 =
         0.01999   -0.00350    0.00673    0.00042
AFIX  43
H3A   2    0.883767    0.556995    0.214660    11.00000   -1.20000
AFIX   0
C4    1    0.820817    0.862147    0.154075    11.00000    0.01829    0.02377 =
         0.02309   -0.00461    0.01215   -0.00387
AFIX  43
H4A   2    0.861684    0.886337    0.135451    11.00000   -1.20000
AFIX   0
C5    1    0.747307    1.020573    0.133744    11.00000    0.02032    0.01880 =
         0.01758   -0.00252    0.00973   -0.00522
AFIX  43
H5A   2    0.738483    1.153845    0.101558    11.00000   -1.20000
AFIX   0
C6    1    0.686045    0.985790    0.160230    11.00000    0.01512    0.01529 =
         0.01399   -0.00469    0.00622   -0.00385
C7    1    0.603784    1.155354    0.132034    11.00000    0.01797    0.01557 =
         0.02145    0.00050    0.01174   -0.00162
AFIX  23
H7A   2    0.627107    1.312364    0.158082    11.00000   -1.20000
H7B   2    0.576665    1.182581    0.076655    11.00000   -1.20000
AFIX   0
C8    1    0.497535    1.193793    0.185043    11.00000    0.02143    0.01399 =
         0.01405   -0.00128    0.00924   -0.00040
AFIX  43
H8A   2    0.527427    1.332972    0.214864    11.00000   -1.20000
AFIX   0
C9    1    0.468238    0.886935    0.107952    11.00000    0.01398    0.01336 =
         0.01072    0.00040    0.00511    0.00034
C10   1    0.398049    0.564686    0.035706    11.00000    0.01481    0.01408 =
         0.01421    0.00061    0.00741    0.00041
C11   1    0.332804    0.729193    0.100830    11.00000    0.01344    0.01487 =
         0.01292    0.00260    0.00665    0.00167
C12   1    0.402527    0.904580    0.130232    11.00000    0.01652    0.01314 =
         0.01388    0.00016    0.00876    0.00067
C13   1    0.191689    0.438298    0.086539    11.00000    0.01956    0.01711 =
         0.02217    0.00117    0.01295   -0.00217
AFIX  23
H13A  2    0.240896    0.321493    0.095005    11.00000   -1.20000
H13B  2    0.163633    0.380581    0.115951    11.00000   -1.20000
AFIX   0
C14   1    0.116693    0.432153    0.002678    11.00000    0.01332    0.01874 =
         0.01956   -0.00011    0.00987   -0.00006
C15   1    0.102591    0.612761   -0.049269    11.00000    0.01894    0.01785 =
         0.02415    0.00082    0.01222    0.00030
AFIX  43
H15A  2    0.142099    0.750370   -0.032678    11.00000   -1.20000
AFIX   0
C16   1    0.031084    0.593419   -0.125323    11.00000    0.02272    0.02116 =
         0.02251    0.00559    0.01175    0.00475
AFIX  43
H16A  2    0.021894    0.719030   -0.160069    11.00000   -1.20000
AFIX   0
C17   1   -0.027117    0.393224   -0.151267    11.00000    0.01677    0.02517 =
         0.01937    0.00074    0.00681    0.00333
AFIX  43
H17A  2   -0.076083    0.381168   -0.203255    11.00000   -1.20000
AFIX   0
C18   1   -0.012345    0.211334   -0.099799    11.00000    0.01801    0.02028 =
         0.02679   -0.00129    0.01167   -0.00146
AFIX  43
H18A  2   -0.051236    0.072574   -0.116812    11.00000   -1.20000
AFIX   0
C19   1    0.058495    0.229616   -0.023829    11.00000    0.01836    0.01873 =
         0.02349    0.00168    0.01218    0.00034
AFIX  43
H19A  2    0.067666    0.103193    0.010667    11.00000   -1.20000
AFIX   0
H1N5  2    0.430978    0.369563   -0.028878    11.00000    0.02976
H2N5  2    0.338999    0.304508   -0.035790    11.00000    0.02390
HKLF 4 1  1.0000  0.0000  0.0000  0.0000 -1.0000  0.0000 -1.0000  0.0000 -1.0000
REM  mh010_0m in P2(1)/c (100K)
REM R1 =  0.0501 for   3416 Fo > 4sig(Fo)  and  0.0802 for all   4956 data
REM    234 parameters refined using      0 restraints
END
REM Highest difference peak  0.327,  deepest hole -0.577,  1-sigma level  0.081
Q1    1   0.4389  0.8914  0.1211  11.00000  0.05    0.33
Q2    1   0.5063  1.1351  0.1574  11.00000  0.05    0.32
Q3    1   0.3162  0.7302  0.2157  11.00000  0.05    0.29
Q4    1   0.0184  0.9381 -0.1960  11.00000  0.05    0.29
Q5    1   0.7145  0.9984  0.1481  11.00000  0.05    0.29
Q6    1   0.9042  0.5777  0.1980  11.00000  0.05    0.28
Q7    1  -0.1606  0.4163 -0.1985  11.00000  0.05    0.28
Q8    1   0.0155  0.4430 -0.1386  11.00000  0.05    0.28
Q9    1  -0.0200  0.7988 -0.2029  11.00000  0.05    0.27
Q10   1  -0.1438  0.3189 -0.2415  11.00000  0.05    0.27
Q11   1   0.4975  0.9771  0.1242  11.00000  0.05    0.26
Q12   1   0.9380  0.5506  0.2827  11.00000  0.05    0.26
Q13   1   0.5641  1.0376  0.0380  11.00000  0.05    0.25
Q14   1   0.2543  0.3391 -0.0800  11.00000  0.05    0.25
Q15   1   0.3234  0.9062  0.0561  11.00000  0.05    0.25
Q16   1   0.7763  0.7441  0.0441  11.00000  0.05    0.25
Q17   1   0.4963  0.7121  0.0408  11.00000  0.05    0.25
Q18   1   0.0399  0.2016 -0.0643  11.00000  0.05    0.25
Q19   1   0.3018  0.7555 -0.0041  11.00000  0.05    0.24
Q20   1   0.1012  0.5204 -0.0226  11.00000  0.05    0.24
;