##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-04-14
_journal_date_accepted     2009-04-16
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      5
_journal_page_first     o1089
_journal_page_last     o1089
_journal_paper_category     QO
_journal_coeditor_code     DN2448
_publ_contact_author_name     'Alex Yanovsky'
_publ_contact_author_address
;
Pfizer Global Research and Development, La Jolla Labs,
10614 Science Center Drive,
San Diego, CA 92121
USA
;
_publ_contact_author_email     'alex.yanovsky@pfizer.com'
_publ_contact_author_fax     '1(858)678 8244'
_publ_contact_author_phone     '1(858)638 3716'
_publ_section_title
;\
Racemic
N-methyl-4-[2-(methylsulfanyl)pyrimidin-4-yl]-1-(tetrahydrofuran-3-yl)\
-1H-pyrazol-5-amine
;
loop_
    _publ_author_name
    _publ_author_address
    'Zhengyu Liu'
;
Pfizer Global Research and Development, La Jolla Laboratories,
10770 Science Center Drive,
San Diego, CA 92121
USA
;
    'Kevin K.-C. Liu'
;
Pfizer Global Research and Development, La Jolla Laboratories,
10770 Science Center Drive,
San Diego, CA 92121
USA
;
    'Arnold L. Rheingold'
;
Department of Chemistry and Biochemistry,
University of California, San Diego,
9500 Gilman Drive, La Jolla, CA 92093,
USA
;
    'Antonio DiPasquale'
;
Department of Chemistry and Biochemistry,
University of California, San Diego,
9500 Gilman Drive, La Jolla, CA 92093,
USA
;
    'Alex Yanovsky'
;
Pfizer Global Research and Development, La Jolla Laboratories,
10770 Science Center Drive,
San Diego, CA 92121
USA
;
data_I
_chemical_name_systematic
;
Racemic N-methyl-4-[2-(methylsulfanyl)pyrimidin-4-yl]-
1-(tetrahydrofuran-3-yl)-1H-pyrazol-5-amine
;
_chemical_name_common     110649-0403-002
_chemical_formula_moiety     'C13 H17 N5 O S'
_chemical_formula_sum     'C13 H17 N5 O S'
_chemical_formula_iupac     'C13 H17 N5 O S'
_chemical_formula_weight     291.38
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     15.7404(5)
_cell_length_b     10.1515(3)
_cell_length_c     18.9644(6)
_cell_angle_alpha     90.00
_cell_angle_beta     112.8290(10)
_cell_angle_gamma     90.00
_cell_volume     2792.92(15)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     1033
_cell_measurement_theta_min     4.9
_cell_measurement_theta_max     54.9
_cell_measurement_temperature     100(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     0.20
_exptl_crystal_density_diffrn     1.386
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1232
_exptl_absorpt_coefficient_mu     2.10
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.572
_exptl_absorpt_correction_T_max     0.679
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker P4/APEX CCD'
_diffrn_measurement_method     ω
_diffrn_reflns_number     18618
_diffrn_reflns_av_R_equivalents     0.030
_diffrn_reflns_av_sigmaI/netI     0.029
_diffrn_reflns_theta_min     3.1
_diffrn_reflns_theta_max     68.6
_diffrn_reflns_theta_full     67.0
_diffrn_measured_fraction_theta_max     0.974
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_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 >
σ(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     5007
_reflns_number_gt     4521
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.046
_refine_ls_R_factor_gt     0.043
_refine_ls_wR_factor_gt     0.116
_refine_ls_wR_factor_ref     0.119
_refine_ls_goodness_of_fit_ref     1.05
_refine_ls_restrained_S_all     1.05
_refine_ls_number_reflns     5007
_refine_ls_number_parameters     371
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
          'calc w=1/[σ²(Fo²)+(0.0596P)²+1.859P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.88
_refine_diff_density_min     -0.32
_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     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SAINT (Bruker, 1997)'
_computing_data_reduction     'SAINT (Bruker, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-32 (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    C C1 0.22461(16) -0.1765(2) 0.31756(13) 0.0393(5) Uani d . 1 . .
    H H1A 0.1969 -0.2521 0.2834 0.047 Uiso calc R 1 . .
    H H1B 0.2861 -0.1583 0.3170 0.047 Uiso calc R 1 . .
    C C2 0.16265(14) -0.0551(2) 0.29178(11) 0.0310(4) Uani d . 1 . .
    H H2A 0.0969 -0.0805 0.2670 0.037 Uiso calc R 1 . .
    H H2B 0.1794 -0.0008 0.2558 0.037 Uiso calc R 1 . .
    C C3 0.18197(12) 0.01907(18) 0.36747(10) 0.0213(4) Uani d . 1 . .
    H H3 0.2191 0.0998 0.3691 0.026 Uiso calc R 1 . .
    C C4 0.24143(13) -0.07910(18) 0.42835(11) 0.0249(4) Uani d . 1 . .
    H H4A 0.3068 -0.0511 0.4489 0.030 Uiso calc R 1 . .
    H H4B 0.2204 -0.0836 0.4712 0.030 Uiso calc R 1 . .
    C C5 -0.01506(12) 0.02935(18) 0.41206(10) 0.0208(4) Uani d . 1 . .
    H H5 -0.0595 -0.0101 0.4279 0.025 Uiso calc R 1 . .
    C C6 -0.01006(12) 0.16645(17) 0.40075(10) 0.0199(4) Uani d . 1 . .
    C C7 0.06411(12) 0.17913(17) 0.37729(10) 0.0196(4) Uani d . 1 . .
    C C8 0.11656(13) 0.29925(19) 0.28860(11) 0.0263(4) Uani d . 1 . .
    H H8A 0.1802 0.2726 0.2992 0.039 Uiso calc R 1 . .
    H H8B 0.1069 0.3899 0.2693 0.039 Uiso calc R 1 . .
    H H8C 0.0740 0.2402 0.2501 0.039 Uiso calc R 1 . .
    C C9 -0.06565(12) 0.27261(18) 0.41090(10) 0.0203(4) Uani d . 1 . .
    C C10 -0.13890(13) 0.25167(19) 0.43403(11) 0.0256(4) Uani d . 1 . .
    H H10 -0.1566 0.1654 0.4423 0.031 Uiso calc R 1 . .
    C C11 -0.18401(13) 0.3611(2) 0.44425(11) 0.0289(4) Uani d . 1 . .
    H H11 -0.2330 0.3485 0.4611 0.035 Uiso calc R 1 . .
    C C12 -0.09392(12) 0.49396(18) 0.40780(10) 0.0231(4) Uani d . 1 . .
    C C13 0.02328(15) 0.6340(2) 0.35791(13) 0.0331(5) Uani d . 1 . .
    H H13A 0.0731 0.5852 0.3971 0.050 Uiso calc R 1 . .
    H H13B 0.0462 0.7201 0.3499 0.050 Uiso calc R 1 . .
    H H13C 0.0015 0.5842 0.3099 0.050 Uiso calc R 1 . .
    C C14 -0.23088(16) 0.4429(2) 0.17690(13) 0.0387(5) Uani d . 1 . .
    H H14A -0.2920 0.4220 0.1775 0.046 Uiso calc R 1 . .
    H H14B -0.2054 0.5207 0.2098 0.046 Uiso calc R 1 . .
    C C15 -0.16593(14) 0.3254(2) 0.20499(11) 0.0324(5) Uani d . 1 . .
    H H15A -0.1816 0.2714 0.2417 0.039 Uiso calc R 1 . .
    H H15B -0.1009 0.3544 0.2295 0.039 Uiso calc R 1 . .
    C C16 -0.18296(12) 0.24857(18) 0.13061(10) 0.0220(4) Uani d . 1 . .
    H H16 -0.2189 0.1669 0.1297 0.026 Uiso calc R 1 . .
    C C17 -0.24264(13) 0.34274(19) 0.06774(11) 0.0271(4) Uani d . 1 . .
    H H17A -0.2190 0.3484 0.0265 0.033 Uiso calc R 1 . .
    H H17B -0.3071 0.3110 0.0454 0.033 Uiso calc R 1 . .
    C C18 0.01589(12) 0.24134(17) 0.08857(10) 0.0204(4) Uani d . 1 . .
    H H18 0.0601 0.2813 0.0726 0.025 Uiso calc R 1 . .
    C C19 0.01176(12) 0.10435(17) 0.10037(10) 0.0191(4) Uani d . 1 . .
    C C20 -0.06290(12) 0.09089(17) 0.12278(9) 0.0188(3) Uani d . 1 . .
    C C21 -0.11957(13) -0.03136(19) 0.20869(11) 0.0262(4) Uani d . 1 . .
    H H21A -0.0808 0.0312 0.2471 0.039 Uiso calc R 1 . .
    H H21B -0.1069 -0.1210 0.2293 0.039 Uiso calc R 1 . .
    H H21C -0.1847 -0.0103 0.1958 0.039 Uiso calc R 1 . .
    C C22 0.06828(11) -0.00076(18) 0.09110(9) 0.0193(4) Uani d . 1 . .
    C C23 0.14461(12) 0.02003(18) 0.07200(10) 0.0224(4) Uani d . 1 . .
    H H23 0.1631 0.1063 0.0646 0.027 Uiso calc R 1 . .
    C C24 0.19188(12) -0.08969(19) 0.06428(11) 0.0247(4) Uani d . 1 . .
    H H24 0.2430 -0.0772 0.0502 0.030 Uiso calc R 1 . .
    C C25 0.09580(12) -0.22284(18) 0.09390(10) 0.0216(4) Uani d . 1 . .
    C C26 -0.03578(16) -0.3636(2) 0.12571(14) 0.0366(5) Uani d . 1 . .
    H H26A -0.0215 -0.3133 0.1730 0.055 Uiso calc R 1 . .
    H H26B -0.0608 -0.4498 0.1308 0.055 Uiso calc R 1 . .
    H H26C -0.0814 -0.3155 0.0829 0.055 Uiso calc R 1 . .
    N N1 0.09784(10) 0.05689(15) 0.37756(8) 0.0199(3) Uani d . 1 . .
    N N2 0.04867(10) -0.03777(15) 0.39826(8) 0.0217(3) Uani d . 1 . .
    N N3 0.09942(11) 0.29183(15) 0.35925(9) 0.0220(3) Uani d . 1 . .
    N N4 -0.16316(11) 0.48479(16) 0.43195(10) 0.0283(4) Uani d . 1 . .
    N N5 -0.04410(10) 0.39615(15) 0.39708(8) 0.0212(3) Uani d . 1 . .
    N N6 -0.09717(10) 0.21269(14) 0.12244(8) 0.0197(3) Uani d . 1 . .
    N N7 -0.04837(10) 0.30785(14) 0.10218(8) 0.0215(3) Uani d . 1 . .
    N N8 -0.09920(11) -0.02230(15) 0.13985(9) 0.0215(3) Uani d . 1 . .
    N N9 0.16958(10) -0.21327(16) 0.07561(9) 0.0249(3) Uani d . 1 . .
    N N10 0.04399(10) -0.12520(15) 0.10180(8) 0.0200(3) Uani d . 1 . .
    O O1 0.23183(11) -0.20351(14) 0.39248(9) 0.0365(4) Uani d . 1 . .
    O O2 -0.23835(12) 0.46761(15) 0.10208(9) 0.0398(4) Uani d . 1 . .
    S S1 -0.07026(3) 0.65654(5) 0.38885(3) 0.02884(14) Uani d . 1 . .
    S S2 0.06756(3) -0.38593(4) 0.10801(3) 0.02817(14) Uani d . 1 . .
    H H3N 0.0715(16) 0.355(2) 0.3657(13) 0.034 Uiso d . 1 . .
    H H8N -0.0682(16) -0.085(2) 0.1349(13) 0.034 Uiso d . 1 . .
_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
    C1 O1 . 1.408(3) ?
    C1 C2 . 1.529(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 C3 . 1.543(2) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 N1 . 1.461(2) ?
    C3 C4 . 1.537(2) ?
    C3 H3 . 1.0000 ?
    C4 O1 . 1.415(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 N2 . 1.320(2) ?
    C5 C6 . 1.415(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.407(2) ?
    C6 C9 . 1.447(2) ?
    C7 N1 . 1.349(2) ?
    C7 N3 . 1.372(2) ?
    C8 N3 . 1.468(2) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
    C9 N5 . 1.351(2) ?
    C9 C10 . 1.400(2) ?
    C10 C11 . 1.372(3) ?
    C10 H10 . 0.9500 ?
    C11 N4 . 1.341(3) ?
    C11 H11 . 0.9500 ?
    C12 N5 . 1.329(2) ?
    C12 N4 . 1.339(2) ?
    C12 S1 . 1.7594(19) ?
    C13 S1 . 1.799(2) ?
    C13 H13A . 0.9800 ?
    C13 H13B . 0.9800 ?
    C13 H13C . 0.9800 ?
    C14 O2 . 1.400(3) ?
    C14 C15 . 1.526(3) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.541(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 N6 . 1.464(2) ?
    C16 C17 . 1.533(2) ?
    C16 H16 . 1.0000 ?
    C17 O2 . 1.415(2) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 N7 . 1.322(2) ?
    C18 C19 . 1.414(2) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.403(2) ?
    C19 C22 . 1.443(2) ?
    C20 N6 . 1.348(2) ?
    C20 N8 . 1.377(2) ?
    C21 N8 . 1.463(2) ?
    C21 H21A . 0.9800 ?
    C21 H21B . 0.9800 ?
    C21 H21C . 0.9800 ?
    C22 N10 . 1.358(2) ?
    C22 C23 . 1.399(2) ?
    C23 C24 . 1.378(3) ?
    C23 H23 . 0.9500 ?
    C24 N9 . 1.342(2) ?
    C24 H24 . 0.9500 ?
    C25 N10 . 1.328(2) ?
    C25 N9 . 1.338(2) ?
    C25 S2 . 1.7614(19) ?
    C26 S2 . 1.798(2) ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    N1 N2 . 1.383(2) ?
    N3 H3N . 0.82(2) ?
    N6 N7 . 1.378(2) ?
    N8 H8N . 0.83(2) ?
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
    O1 C1 C2 . . 105.75(16) ?
    O1 C1 H1A . . 110.6 ?
    C2 C1 H1A . . 110.6 ?
    O1 C1 H1B . . 110.6 ?
    C2 C1 H1B . . 110.6 ?
    H1A C1 H1B . . 108.7 ?
    C1 C2 C3 . . 102.99(15) ?
    C1 C2 H2A . . 111.2 ?
    C3 C2 H2A . . 111.2 ?
    C1 C2 H2B . . 111.2 ?
    C3 C2 H2B . . 111.2 ?
    H2A C2 H2B . . 109.1 ?
    N1 C3 C4 . . 112.99(14) ?
    N1 C3 C2 . . 112.86(14) ?
    C4 C3 C2 . . 103.01(15) ?
    N1 C3 H3 . . 109.3 ?
    C4 C3 H3 . . 109.3 ?
    C2 C3 H3 . . 109.3 ?
    O1 C4 C3 . . 107.29(15) ?
    O1 C4 H4A . . 110.3 ?
    C3 C4 H4A . . 110.3 ?
    O1 C4 H4B . . 110.3 ?
    C3 C4 H4B . . 110.3 ?
    H4A C4 H4B . . 108.5 ?
    N2 C5 C6 . . 112.72(15) ?
    N2 C5 H5 . . 123.6 ?
    C6 C5 H5 . . 123.6 ?
    C7 C6 C5 . . 103.87(15) ?
    C7 C6 C9 . . 126.33(16) ?
    C5 C6 C9 . . 129.80(16) ?
    N1 C7 N3 . . 124.83(16) ?
    N1 C7 C6 . . 106.75(15) ?
    N3 C7 C6 . . 128.40(16) ?
    N3 C8 H8A . . 109.5 ?
    N3 C8 H8B . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    N3 C8 H8C . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
    N5 C9 C10 . . 120.07(16) ?
    N5 C9 C6 . . 117.08(15) ?
    C10 C9 C6 . . 122.86(16) ?
    C11 C10 C9 . . 117.09(17) ?
    C11 C10 H10 . . 121.5 ?
    C9 C10 H10 . . 121.5 ?
    N4 C11 C10 . . 123.96(17) ?
    N4 C11 H11 . . 118.0 ?
    C10 C11 H11 . . 118.0 ?
    N5 C12 N4 . . 127.39(18) ?
    N5 C12 S1 . . 119.05(14) ?
    N4 C12 S1 . . 113.57(14) ?
    S1 C13 H13A . . 109.5 ?
    S1 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 109.5 ?
    S1 C13 H13C . . 109.5 ?
    H13A C13 H13C . . 109.5 ?
    H13B C13 H13C . . 109.5 ?
    O2 C14 C15 . . 105.96(16) ?
    O2 C14 H14A . . 110.5 ?
    C15 C14 H14A . . 110.5 ?
    O2 C14 H14B . . 110.5 ?
    C15 C14 H14B . . 110.5 ?
    H14A C14 H14B . . 108.7 ?
    C14 C15 C16 . . 102.77(16) ?
    C14 C15 H15A . . 111.2 ?
    C16 C15 H15A . . 111.2 ?
    C14 C15 H15B . . 111.2 ?
    C16 C15 H15B . . 111.2 ?
    H15A C15 H15B . . 109.1 ?
    N6 C16 C17 . . 112.64(14) ?
    N6 C16 C15 . . 112.50(15) ?
    C17 C16 C15 . . 103.46(15) ?
    N6 C16 H16 . . 109.4 ?
    C17 C16 H16 . . 109.4 ?
    C15 C16 H16 . . 109.4 ?
    O2 C17 C16 . . 107.18(15) ?
    O2 C17 H17A . . 110.3 ?
    C16 C17 H17A . . 110.3 ?
    O2 C17 H17B . . 110.3 ?
    C16 C17 H17B . . 110.3 ?
    H17A C17 H17B . . 108.5 ?
    N7 C18 C19 . . 112.69(16) ?
    N7 C18 H18 . . 123.7 ?
    C19 C18 H18 . . 123.7 ?
    C20 C19 C18 . . 103.83(15) ?
    C20 C19 C22 . . 126.39(16) ?
    C18 C19 C22 . . 129.77(16) ?
    N6 C20 N8 . . 124.39(16) ?
    N6 C20 C19 . . 106.85(15) ?
    N8 C20 C19 . . 128.72(16) ?
    N8 C21 H21A . . 109.5 ?
    N8 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    N8 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
    N10 C22 C23 . . 119.94(16) ?
    N10 C22 C19 . . 116.56(15) ?
    C23 C22 C19 . . 123.50(16) ?
    C24 C23 C22 . . 117.31(17) ?
    C24 C23 H23 . . 121.3 ?
    C22 C23 H23 . . 121.3 ?
    N9 C24 C23 . . 123.55(17) ?
    N9 C24 H24 . . 118.2 ?
    C23 C24 H24 . . 118.2 ?
    N10 C25 N9 . . 127.40(17) ?
    N10 C25 S2 . . 118.83(14) ?
    N9 C25 S2 . . 113.77(13) ?
    S2 C26 H26A . . 109.5 ?
    S2 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    S2 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C7 N1 N2 . . 112.18(14) ?
    C7 N1 C3 . . 128.07(15) ?
    N2 N1 C3 . . 119.35(14) ?
    C5 N2 N1 . . 104.46(14) ?
    C7 N3 C8 . . 120.42(15) ?
    C7 N3 H3N . . 109.2(17) ?
    C8 N3 H3N . . 113.3(17) ?
    C12 N4 C11 . . 114.28(16) ?
    C12 N5 C9 . . 117.16(16) ?
    C20 N6 N7 . . 112.26(14) ?
    C20 N6 C16 . . 127.71(15) ?
    N7 N6 C16 . . 119.47(14) ?
    C18 N7 N6 . . 104.35(14) ?
    C20 N8 C21 . . 121.13(15) ?
    C20 N8 H8N . . 107.4(17) ?
    C21 N8 H8N . . 113.2(16) ?
    C25 N9 C24 . . 114.62(16) ?
    C25 N10 C22 . . 117.17(15) ?
    C1 O1 C4 . . 105.24(15) ?
    C14 O2 C17 . . 106.04(16) ?
    C12 S1 C13 . . 102.24(9) ?
    C25 S2 C26 . . 102.10(9) ?
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
    N3 H3N N5 . 0.82(2) 2.16(2) 2.828(2) 139(2)
    N8 H8N N10 . 0.83(2) 2.13(2) 2.820(2) 140(2)
