##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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/  #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2007-07-24
_journal_date_accepted     2007-07-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue     10
_journal_page_first     o3942
_journal_page_last     o3942
_journal_paper_category     QO
_journal_coeditor_code     CI2429
_publ_contact_author_name     'Professor Yan-Ping He'
_publ_contact_author_address
;
School of Chemical Science and Technology
Key Laboratory of Medicinal Chemistry for Natural Resources
Ministry of Education
Yunnan University
Kunming 650091
People's Republic of China
;
_publ_contact_author_email     yphe@ynu.edu.cn
_publ_contact_author_fax     '86-0871-5031391'
_publ_contact_author_phone     '86-0871-5031391'
_publ_section_title
;
2-(Benzoylmethylsulfanyl)-6-benzyl-5-isopropylpyrimidin-4(3H)-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Rao, Zhi-Kun'
;
School of Chemical Science and Technology
Key Laboratory of Medicinal Chemistry for Natural Resources
Ministry of Education
Yunnan University
Kunming 650091
People's Republic of China
;
    'Zhang, Sui-Shuan'
;
School of Chemical Science and Technology
Key Laboratory of Medicinal Chemistry for Natural Resources
Ministry of Education
Yunnan University
Kunming 650091
People's Republic of China
;
    'He, Yan-Ping'
;
School of Chemical Science and Technology
Key Laboratory of Medicinal Chemistry for Natural Resources
Ministry of Education
Yunnan University
Kunming 650091
People's Republic of China
;
    'Zheng, Yong-Tang'
;
Laboratory of Molecular Immunopharmacology
Key Laboratory of Animal Models and Human Disease Mechanisms
Kunming Institute of Zoology
Chinese Academy of Sciences
Kunming
Yunnan 650223
People's Republic of China
;
    'Li, Cong'
;
School of Chemical Science and Technology
Key Laboratory of Medicinal Chemistry for Natural Resources
Ministry of Education
Yunnan University
Kunming 650091
People's Republic of China
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-(Benzoylmethylsulfanyl)-6-benzyl-5-isopropylpyrimidin-4(3H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H22 N2 O2 S'
_chemical_formula_sum     'C22 H22 N2 O2 S'
_chemical_formula_iupac     'C22 H22 N2 O2 S'
_chemical_formula_weight     378.48
_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     8.691(2)
_cell_length_b     23.223(6)
_cell_length_c     10.705(3)
_cell_angle_alpha     90.00
_cell_angle_beta     111.949(4)
_cell_angle_gamma     90.00
_cell_volume     2004.1(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min     1.75
_cell_measurement_theta_max     27.02
_cell_measurement_temperature     298(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.19
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.254
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     800
_exptl_absorpt_coefficient_mu     0.180
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 1998)'
_exptl_absorpt_correction_T_min     0.961
_exptl_absorpt_correction_T_max     0.987
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12473
_diffrn_reflns_av_R_equivalents     0.1027
_diffrn_reflns_av_sigmaI/netI     0.1538
_diffrn_reflns_theta_min     1.75
_diffrn_reflns_theta_max     27.02
_diffrn_reflns_theta_full     27.02
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     29
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4358
_reflns_number_gt     1348
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.2323
_refine_ls_R_factor_gt     0.0654
_refine_ls_wR_factor_gt     0.1012
_refine_ls_wR_factor_ref     0.1376
_refine_ls_goodness_of_fit_ref     0.996
_refine_ls_restrained_S_all     0.996
_refine_ls_number_reflns     4358
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'calc w = 1/[σ²(Fo²)+(0.039P)²] where P=(Fo²+2Fc²)'
_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     0.189
_refine_diff_density_min     -0.182
_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'
    'O' 'O' 0.0106 0.0060
                         '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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1998)'
_computing_publication_material     'SHELXTL'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    S S1 0.74405(15) 0.14324(5) 0.58050(11) 0.0803(4) Uani d . 1 . .
    O O1 0.5071(3) 0.23901(12) 0.4777(3) 0.0893(10) Uani d . 1 . .
    O O2 0.3701(3) -0.00995(11) 0.5886(2) 0.0705(8) Uani d . 1 . .
    N N1 0.5429(4) 0.06432(13) 0.6032(3) 0.0591(9) Uani d . 1 . .
    H H1A 0.5734 0.0479 0.5442 0.071 Uiso calc R 1 . .
    N N2 0.5769(4) 0.14324(13) 0.7453(3) 0.0720(10) Uani d . 1 . .
    C C1 0.6581(5) 0.31823(17) 0.5976(4) 0.0521(10) Uani d . 1 . .
    C C2 0.5386(5) 0.3564(2) 0.5210(4) 0.0753(13) Uani d . 1 . .
    H H2B 0.4443 0.3426 0.4523 0.090 Uiso calc R 1 . .
    C C3 0.5575(6) 0.4147(2) 0.5452(5) 0.0975(16) Uani d . 1 . .
    H H3A 0.4763 0.4401 0.4927 0.117 Uiso calc R 1 . .
    C C4 0.6947(7) 0.4352(2) 0.6456(6) 0.1010(17) Uani d . 1 . .
    H H4A 0.7071 0.4746 0.6611 0.121 Uiso calc R 1 . .
    C C5 0.8153(6) 0.3981(2) 0.7244(4) 0.0914(15) Uani d . 1 . .
    H H5A 0.9089 0.4122 0.7934 0.110 Uiso calc R 1 . .
    C C6 0.7952(5) 0.33933(19) 0.6994(4) 0.0718(12) Uani d . 1 . .
    H H6A 0.8760 0.3140 0.7525 0.086 Uiso calc R 1 . .
    C C7 0.6320(5) 0.25571(18) 0.5645(4) 0.0577(11) Uani d . 1 . .
    C C8 0.7706(5) 0.21571(14) 0.6419(4) 0.0666(12) Uani d . 1 . .
    H H8A 0.7811 0.2154 0.7353 0.080 Uiso calc R 1 . .
    H H8B 0.8735 0.2307 0.6391 0.080 Uiso calc R 1 . .
    C C9 0.6094(5) 0.11632(16) 0.6528(4) 0.0594(11) Uani d . 1 . .
    C C10 0.4286(5) 0.03664(18) 0.6432(4) 0.0588(11) Uani d . 1 . .
    C C11 0.3910(5) 0.06488(17) 0.7479(4) 0.0591(11) Uani d . 1 . .
    C C12 0.4662(6) 0.11664(18) 0.7929(4) 0.0717(13) Uani d . 1 . .
    C C13 0.2691(5) 0.03583(18) 0.7980(4) 0.0761(13) Uani d . 1 . .
    H H13A 0.2676 0.0580 0.8754 0.091 Uiso calc R 1 . .
    C C14 0.3136(5) -0.02547(18) 0.8449(4) 0.0980(15) Uani d . 1 . .
    H H14A 0.2296 -0.0413 0.8728 0.147 Uiso calc R 1 . .
    H H14B 0.4184 -0.0260 0.9193 0.147 Uiso calc R 1 . .
    H H14C 0.3212 -0.0481 0.7723 0.147 Uiso calc R 1 . .
    C C15 0.0966(6) 0.0379(2) 0.6919(5) 0.143(2) Uani d . 1 . .
    H H15A 0.0693 0.0769 0.6621 0.215 Uiso calc R 1 . .
    H H15B 0.0188 0.0238 0.7289 0.215 Uiso calc R 1 . .
    H H15C 0.0916 0.0143 0.6169 0.215 Uiso calc R 1 . .
    C C16 0.4398(6) 0.15025(17) 0.9048(4) 0.1119(18) Uani d . 1 . .
    H H16A 0.3314 0.1407 0.9053 0.134 Uiso calc R 1 . .
    H H16B 0.5221 0.1381 0.9904 0.134 Uiso calc R 1 . .
    C C17 0.4508(7) 0.21374(19) 0.8932(5) 0.0658(12) Uani d . 1 . .
    C C18 0.3165(7) 0.2464(3) 0.8216(5) 0.0944(16) Uani d . 1 . .
    H H18A 0.2148 0.2283 0.7786 0.113 Uiso calc R 1 . .
    C C19 0.3263(9) 0.3049(4) 0.8110(6) 0.118(2) Uani d . 1 . .
    H H19A 0.2322 0.3262 0.7624 0.142 Uiso calc R 1 . .
    C C20 0.4709(11) 0.3311(3) 0.8706(7) 0.112(2) Uani d . 1 . .
    H H20A 0.4779 0.3707 0.8610 0.135 Uiso calc R 1 . .
    C C21 0.6078(7) 0.3015(3) 0.9445(6) 0.1028(18) Uani d . 1 . .
    H H21A 0.7078 0.3205 0.9880 0.123 Uiso calc R 1 . .
    C C22 0.5972(7) 0.2424(3) 0.9547(4) 0.0835(14) Uani d . 1 . .
    H H22A 0.6919 0.2217 1.0046 0.100 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
    S1 0.1087(9) 0.0565(8) 0.1015(9) -0.0011(7) 0.0689(8) -0.0034(7)
    O1 0.070(2) 0.086(2) 0.088(2) -0.0099(18) 0.0023(17) -0.0288(18)
    O2 0.094(2) 0.0537(19) 0.079(2) -0.0062(16) 0.0503(17) -0.0155(15)
    N1 0.086(2) 0.045(2) 0.060(2) 0.0038(19) 0.0430(19) -0.0075(18)
    N2 0.115(3) 0.051(2) 0.072(2) -0.011(2) 0.061(2) -0.0165(19)
    C1 0.057(3) 0.051(3) 0.051(3) 0.005(2) 0.023(2) 0.008(2)
    C2 0.085(3) 0.071(3) 0.073(3) -0.003(3) 0.032(3) -0.004(3)
    C3 0.098(4) 0.085(5) 0.108(4) 0.021(4) 0.036(3) 0.017(3)
    C4 0.137(6) 0.058(4) 0.127(5) 0.001(4) 0.071(4) 0.002(4)
    C5 0.109(4) 0.071(4) 0.087(4) -0.032(3) 0.029(3) -0.018(3)
    C6 0.081(3) 0.065(3) 0.064(3) -0.014(3) 0.022(3) -0.003(2)
    C7 0.064(3) 0.058(3) 0.054(3) -0.005(3) 0.026(2) -0.002(2)
    C8 0.081(3) 0.052(3) 0.069(3) -0.005(2) 0.030(2) 0.000(2)
    C9 0.082(3) 0.045(3) 0.062(3) 0.007(2) 0.039(2) 0.003(2)
    C10 0.071(3) 0.052(3) 0.061(3) 0.006(3) 0.033(2) 0.004(2)
    C11 0.084(3) 0.049(3) 0.059(3) 0.004(2) 0.043(2) -0.004(2)
    C12 0.121(4) 0.048(3) 0.067(3) 0.008(3) 0.058(3) -0.001(2)
    C13 0.103(4) 0.063(3) 0.090(3) 0.002(3) 0.068(3) -0.009(3)
    C14 0.129(4) 0.076(4) 0.107(4) -0.016(3) 0.065(3) 0.011(3)
    C15 0.078(4) 0.191(6) 0.177(5) 0.037(4) 0.068(4) 0.058(5)
    C16 0.220(6) 0.054(3) 0.107(4) -0.017(4) 0.112(4) -0.029(3)
    C17 0.096(4) 0.057(3) 0.064(3) -0.002(3) 0.053(3) -0.016(3)
    C18 0.095(4) 0.113(5) 0.072(4) 0.007(4) 0.027(3) -0.022(4)
    C19 0.128(6) 0.142(7) 0.089(4) 0.068(5) 0.045(4) 0.021(5)
    C20 0.175(7) 0.079(5) 0.121(6) 0.024(5) 0.098(6) 0.004(4)
    C21 0.101(5) 0.104(5) 0.121(5) -0.031(4) 0.061(4) -0.047(4)
    C22 0.089(4) 0.084(4) 0.078(3) 0.019(3) 0.033(3) -0.011(3)
_geom_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
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 C9 . 1.743(4) ?
    S1 C8 . 1.790(3) ?
    O1 C7 . 1.199(4) ?
    O2 C10 . 1.244(4) ?
    N1 C9 . 1.358(4) ?
    N1 C10 . 1.379(4) ?
    N1 H1A . 0.86 ?
    N2 C9 . 1.288(4) ?
    N2 C12 . 1.391(4) ?
    C1 C6 . 1.370(5) ?
    C1 C2 . 1.379(5) ?
    C1 C7 . 1.491(5) ?
    C2 C3 . 1.376(5) ?
    C2 H2B . 0.93 ?
    C3 C4 . 1.358(5) ?
    C3 H3A . 0.93 ?
    C4 C5 . 1.376(5) ?
    C4 H4A . 0.93 ?
    C5 C6 . 1.389(5) ?
    C5 H5A . 0.93 ?
    C6 H6A . 0.93 ?
    C7 C8 . 1.502(5) ?
    C8 H8A . 0.97 ?
    C8 H8B . 0.97 ?
    C10 C11 . 1.438(4) ?
    C11 C12 . 1.367(5) ?
    C11 C13 . 1.514(5) ?
    C12 C16 . 1.518(5) ?
    C13 C15 . 1.506(5) ?
    C13 C14 . 1.511(5) ?
    C13 H13A . 0.98 ?
    C14 H14A . 0.96 ?
    C14 H14B . 0.96 ?
    C14 H14C . 0.96 ?
    C15 H15A . 0.96 ?
    C15 H15B . 0.96 ?
    C15 H15C . 0.96 ?
    C16 C17 . 1.486(5) ?
    C16 H16A . 0.97 ?
    C16 H16B . 0.97 ?
    C17 C18 . 1.362(6) ?
    C17 C22 . 1.367(5) ?
    C18 C19 . 1.370(7) ?
    C18 H18A . 0.93 ?
    C19 C20 . 1.325(7) ?
    C19 H19A . 0.93 ?
    C20 C21 . 1.344(6) ?
    C20 H20A . 0.93 ?
    C21 C22 . 1.383(6) ?
    C21 H21A . 0.93 ?
    C22 H22A . 0.93 ?
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
    C9 S1 C8 . . 100.97(18) ?
    C9 N1 C10 . . 122.9(3) ?
    C9 N1 H1A . . 118.5 ?
    C10 N1 H1A . . 118.5 ?
    C9 N2 C12 . . 116.5(3) ?
    C6 C1 C2 . . 118.8(4) ?
    C6 C1 C7 . . 123.2(4) ?
    C2 C1 C7 . . 118.1(4) ?
    C3 C2 C1 . . 120.7(4) ?
    C3 C2 H2B . . 119.7 ?
    C1 C2 H2B . . 119.7 ?
    C4 C3 C2 . . 120.1(5) ?
    C4 C3 H3A . . 119.9 ?
    C2 C3 H3A . . 119.9 ?
    C3 C4 C5 . . 120.5(5) ?
    C3 C4 H4A . . 119.7 ?
    C5 C4 H4A . . 119.7 ?
    C4 C5 C6 . . 119.0(4) ?
    C4 C5 H5A . . 120.5 ?
    C6 C5 H5A . . 120.5 ?
    C1 C6 C5 . . 120.9(4) ?
    C1 C6 H6A . . 119.5 ?
    C5 C6 H6A . . 119.5 ?
    O1 C7 C1 . . 120.8(4) ?
    O1 C7 C8 . . 122.3(4) ?
    C1 C7 C8 . . 116.8(4) ?
    C7 C8 S1 . . 114.4(3) ?
    C7 C8 H8A . . 108.7 ?
    S1 C8 H8A . . 108.7 ?
    C7 C8 H8B . . 108.7 ?
    S1 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    N2 C9 N1 . . 123.3(3) ?
    N2 C9 S1 . . 122.9(3) ?
    N1 C9 S1 . . 113.8(3) ?
    O2 C10 N1 . . 118.4(4) ?
    O2 C10 C11 . . 126.2(4) ?
    N1 C10 C11 . . 115.4(4) ?
    C12 C11 C10 . . 117.2(4) ?
    C12 C11 C13 . . 124.9(4) ?
    C10 C11 C13 . . 117.8(4) ?
    C11 C12 N2 . . 124.5(3) ?
    C11 C12 C16 . . 122.5(4) ?
    N2 C12 C16 . . 113.0(4) ?
    C15 C13 C14 . . 109.9(4) ?
    C15 C13 C11 . . 110.5(4) ?
    C14 C13 C11 . . 114.3(3) ?
    C15 C13 H13A . . 107.3 ?
    C14 C13 H13A . . 107.3 ?
    C11 C13 H13A . . 107.3 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C15 H15A . . 109.5 ?
    C13 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    C13 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    C17 C16 C12 . . 114.2(3) ?
    C17 C16 H16A . . 108.7 ?
    C12 C16 H16A . . 108.7 ?
    C17 C16 H16B . . 108.7 ?
    C12 C16 H16B . . 108.7 ?
    H16A C16 H16B . . 107.6 ?
    C18 C17 C22 . . 116.6(4) ?
    C18 C17 C16 . . 122.1(6) ?
    C22 C17 C16 . . 121.3(5) ?
    C17 C18 C19 . . 122.1(6) ?
    C17 C18 H18A . . 118.9 ?
    C19 C18 H18A . . 118.9 ?
    C20 C19 C18 . . 119.5(7) ?
    C20 C19 H19A . . 120.3 ?
    C18 C19 H19A . . 120.3 ?
    C19 C20 C21 . . 121.4(7) ?
    C19 C20 H20A . . 119.3 ?
    C21 C20 H20A . . 119.3 ?
    C20 C21 C22 . . 118.9(6) ?
    C20 C21 H21A . . 120.6 ?
    C22 C21 H21A . . 120.6 ?
    C17 C22 C21 . . 121.5(5) ?
    C17 C22 H22A . . 119.3 ?
    C21 C22 H22A . . 119.3 ?
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 H1A O2 3_656 0.86 1.89 2.747(4) 177 y
    C6 H6A O1 4_666 0.93 2.56 3.388(5) 148 y
    C8 H8A N2 . 0.97 2.47 2.879(5) 105 y
    C14 H14C O2 . 0.96 2.34 2.984(5) 124 y
