##############################################################################
###                                                                        ###
###        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/  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2010-02-08
_journal_date_accepted     2010-02-09
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      3
_journal_page_first     o632
_journal_page_last     o632
_journal_paper_category     QO
_journal_coeditor_code     BT5192
_publ_contact_author
;
     Dr Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;\
3-[(1-Benzyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-\
1,5-benzodiazepine-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Dardouri, R.'
;
Laboratoire de Chimie Organique Appliqu\'ee
Facult\'e des Sciences et Techniques
Universit\'e Sidi Mohamed Ben Abdallah
F\'es
Morocco
;
    'Kandri Rodi, Y.'
;
Laboratoire de Chimie Organique Appliqu\'ee
Facult\'e des Sciences et Techniques
Universit\'e Sidi Mohamed Ben Abdallah
F\'es
Morocco
;
    'Saffon, Natalie'
;
Service Commun Rayons-X FR2599
Universit\'e Paul Sabatier B\^atiment 2R1
118 Route de Narbonne
Toulouse
France
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique H\'et\'erocyclique
P\^ole de Comp\'etences Pharmacochimie
Universit\'e Mohammed V-Agdal
BP 1014 Avenue Ibn Batout
Rabat
Morocco
;
    'Ng, Seik Weng'
;
Department of Chemistry
University of Malaya
50603 Kuala Lumpur
Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-[(1-Benzyl-1<i>H</i>-1,2,3-triazol-4-yl)methyl]-1,5-dimethyl-
1,5-benzodiazepine-2,4-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H21 N5 O2'
_chemical_formula_sum     'C21 H21 N5 O2'
_chemical_formula_iupac     'C21 H21 N5 O2'
_chemical_formula_weight     375.43
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.3380(3)
_cell_length_b     9.1033(3)
_cell_length_c     13.4796(4)
_cell_angle_alpha     95.385(2)
_cell_angle_beta     107.840(2)
_cell_angle_gamma     101.768(2)
_cell_volume     939.97(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     1894
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     26.8
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.28
_exptl_crystal_size_mid     0.18
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.326
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     396
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     293(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 APEXII diffractometer'
_diffrn_measurement_method     '\f and \w scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     7973
_diffrn_reflns_av_R_equivalents     0.0374
_diffrn_reflns_av_sigmaI/netI     0.0524
_diffrn_reflns_theta_min     1.61
_diffrn_reflns_theta_max     25.00
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3279
_reflns_number_gt     2132
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0775
_refine_ls_R_factor_gt     0.0417
_refine_ls_wR_factor_gt     0.1077
_refine_ls_wR_factor_ref     0.1405
_refine_ls_goodness_of_fit_ref     1.050
_refine_ls_restrained_S_all     1.050
_refine_ls_number_reflns     3279
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^] 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     0.216
_refine_diff_density_min     -0.217
_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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.50707(19) 0.14271(17) 0.38773(13) 0.0383(4) Uani d . 1 . .
    O O2 0.8254(2) 0.2153(2) 0.23619(15) 0.0501(5) Uani d . 1 . .
    N N1 0.8448(2) 0.2106(2) 0.71289(16) 0.0366(5) Uani d . 1 . .
    N N2 0.9062(2) 0.3607(2) 0.71872(16) 0.0376(5) Uani d . 1 . .
    N N3 0.9231(2) 0.3802(2) 0.62613(16) 0.0359(5) Uani d . 1 . .
    N N4 0.4763(2) 0.37357(19) 0.34845(14) 0.0283(4) Uani d . 1 . .
    N N5 0.6925(2) 0.4101(2) 0.21476(15) 0.0310(5) Uani d . 1 . .
    C C1 0.9776(3) 0.1642(3) 0.89419(19) 0.0359(6) Uani d . 1 . .
    C C2 1.0765(3) 0.0598(3) 0.8911(2) 0.0409(6) Uani d . 1 . .
    H H2 1.0396 -0.0190 0.8339 0.049 Uiso calc R 1 . .
    C C3 1.2289(4) 0.0720(4) 0.9720(3) 0.0650(9) Uani d . 1 . .
    H H3 1.2943 0.0013 0.9694 0.078 Uiso calc R 1 . .
    C C4 1.2843(5) 0.1865(6) 1.0557(3) 0.0935(15) Uani d . 1 . .
    H H4 1.3868 0.1928 1.1106 0.112 Uiso calc R 1 . .
    C C5 1.1909(6) 0.2932(5) 1.0604(3) 0.0947(16) Uani d . 1 . .
    H H5 1.2312 0.3731 1.1171 0.114 Uiso calc R 1 . .
    C C6 1.0353(5) 0.2807(3) 0.9796(2) 0.0610(9) Uani d . 1 . .
    H H6 0.9699 0.3512 0.9831 0.073 Uiso calc R 1 . .
    C C7 0.8123(3) 0.1525(3) 0.8049(2) 0.0442(7) Uani d . 1 . .
    H H7A 0.7476 0.0468 0.7836 0.053 Uiso calc R 1 . .
    H H7B 0.7415 0.2096 0.8294 0.053 Uiso calc R 1 . .
    C C8 0.8216(3) 0.1340(3) 0.6177(2) 0.0364(6) Uani d . 1 . .
    H H8 0.7799 0.0296 0.5944 0.044 Uiso calc R 1 . .
    C C9 0.8726(3) 0.2424(3) 0.56202(19) 0.0321(6) Uani d . 1 . .
    C C10 0.8729(3) 0.2271(3) 0.45103(19) 0.0346(6) Uani d . 1 . .
    H H10A 0.8279 0.1209 0.4181 0.042 Uiso calc R 1 . .
    H H10B 0.9915 0.2590 0.4515 0.042 Uiso calc R 1 . .
    C C11 0.5716(3) 0.2698(2) 0.37552(18) 0.0282(5) Uani d . 1 . .
    C C12 0.7630(3) 0.3225(2) 0.38576(18) 0.0284(5) Uani d . 1 . .
    H H12 0.8070 0.4292 0.4202 0.034 Uiso calc R 1 . .
    C C13 0.7673(3) 0.3110(3) 0.27368(19) 0.0324(6) Uani d . 1 . .
    C C14 0.6468(3) 0.5362(2) 0.26045(17) 0.0286(5) Uani d . 1 . .
    C C15 0.6992(3) 0.6803(3) 0.2368(2) 0.0357(6) Uani d . 1 . .
    H H15 0.7607 0.6919 0.1898 0.043 Uiso calc R 1 . .
    C C16 0.6620(3) 0.8055(3) 0.2814(2) 0.0403(6) Uani d . 1 . .
    H H16 0.6977 0.9004 0.2641 0.048 Uiso calc R 1 . .
    C C17 0.5715(3) 0.7908(3) 0.3521(2) 0.0385(6) Uani d . 1 . .
    H H17 0.5500 0.8760 0.3844 0.046 Uiso calc R 1 . .
    C C18 0.5137(3) 0.6485(2) 0.37394(19) 0.0324(5) Uani d . 1 . .
    H H18 0.4513 0.6384 0.4205 0.039 Uiso calc R 1 . .
    C C19 0.5468(3) 0.5196(2) 0.32765(17) 0.0268(5) Uani d . 1 . .
    C C20 0.2922(3) 0.3329(3) 0.3420(2) 0.0364(6) Uani d . 1 . .
    H H20A 0.2357 0.2351 0.2985 0.055 Uiso calc R 1 . .
    H H20B 0.2356 0.4080 0.3118 0.055 Uiso calc R 1 . .
    H H20C 0.2857 0.3293 0.4117 0.055 Uiso calc R 1 . .
    C C21 0.7053(3) 0.4078(3) 0.1087(2) 0.0440(7) Uani d . 1 . .
    H H21A 0.8197 0.4626 0.1138 0.066 Uiso calc R 1 . .
    H H21B 0.6207 0.4549 0.0672 0.066 Uiso calc R 1 . .
    H H21C 0.6841 0.3044 0.0756 0.066 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 0.0331(9) 0.0258(9) 0.0594(12) 0.0034(7) 0.0207(8) 0.0141(8)
    O2 0.0635(12) 0.0451(11) 0.0596(12) 0.0259(9) 0.0373(10) 0.0104(9)
    N1 0.0281(10) 0.0379(12) 0.0463(13) 0.0062(9) 0.0139(9) 0.0187(10)
    N2 0.0316(11) 0.0349(12) 0.0476(13) 0.0078(9) 0.0133(10) 0.0139(9)
    N3 0.0278(10) 0.0370(12) 0.0461(13) 0.0085(9) 0.0138(9) 0.0160(10)
    N4 0.0219(9) 0.0264(10) 0.0388(12) 0.0037(8) 0.0138(8) 0.0080(8)
    N5 0.0315(10) 0.0314(11) 0.0333(11) 0.0061(8) 0.0163(9) 0.0067(9)
    C1 0.0399(13) 0.0350(14) 0.0344(14) -0.0005(11) 0.0197(11) 0.0095(11)
    C2 0.0387(14) 0.0420(15) 0.0435(16) 0.0041(11) 0.0176(12) 0.0138(12)
    C3 0.0380(16) 0.089(2) 0.070(2) 0.0062(16) 0.0172(16) 0.048(2)
    C4 0.061(2) 0.113(3) 0.060(3) -0.043(2) -0.0130(18) 0.048(3)
    C5 0.138(4) 0.069(3) 0.0316(19) -0.049(3) 0.014(2) 0.0020(17)
    C6 0.099(2) 0.0374(16) 0.0501(19) -0.0039(15) 0.0430(19) 0.0055(13)
    C7 0.0399(14) 0.0494(16) 0.0526(17) 0.0084(12) 0.0261(13) 0.0233(13)
    C8 0.0334(13) 0.0277(13) 0.0478(16) 0.0042(10) 0.0139(12) 0.0108(11)
    C9 0.0200(11) 0.0302(13) 0.0494(15) 0.0079(9) 0.0128(10) 0.0147(11)
    C10 0.0288(12) 0.0313(13) 0.0501(16) 0.0102(10) 0.0185(11) 0.0132(11)
    C11 0.0291(12) 0.0243(12) 0.0338(13) 0.0043(9) 0.0153(10) 0.0067(9)
    C12 0.0272(11) 0.0234(11) 0.0385(14) 0.0054(9) 0.0162(10) 0.0074(10)
    C13 0.0292(12) 0.0279(13) 0.0432(15) 0.0034(10) 0.0190(11) 0.0055(11)
    C14 0.0223(11) 0.0300(12) 0.0331(13) 0.0059(9) 0.0084(10) 0.0081(10)
    C15 0.0267(12) 0.0379(14) 0.0472(15) 0.0062(10) 0.0170(11) 0.0185(12)
    C16 0.0310(13) 0.0294(13) 0.0630(18) 0.0065(10) 0.0165(12) 0.0194(12)
    C17 0.0321(13) 0.0273(13) 0.0577(17) 0.0101(10) 0.0153(12) 0.0076(11)
    C18 0.0254(11) 0.0316(13) 0.0411(14) 0.0088(10) 0.0109(10) 0.0068(10)
    C19 0.0229(11) 0.0244(12) 0.0322(13) 0.0053(9) 0.0078(9) 0.0070(9)
    C20 0.0234(12) 0.0421(14) 0.0460(15) 0.0032(10) 0.0164(11) 0.0116(11)
    C21 0.0493(15) 0.0498(16) 0.0386(15) 0.0088(12) 0.0242(13) 0.0103(12)
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 C11 . 1.221(2) ?
    O2 C13 . 1.221(3) ?
    N1 C8 . 1.340(3) ?
    N1 N2 . 1.344(3) ?
    N1 C7 . 1.470(3) ?
    N2 N3 . 1.322(3) ?
    N3 C9 . 1.362(3) ?
    N4 C11 . 1.361(3) ?
    N4 C19 . 1.429(3) ?
    N4 C20 . 1.477(3) ?
    N5 C13 . 1.376(3) ?
    N5 C14 . 1.425(3) ?
    N5 C21 . 1.464(3) ?
    C1 C6 . 1.380(4) ?
    C1 C2 . 1.385(3) ?
    C1 C7 . 1.503(4) ?
    C2 C3 . 1.374(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.355(6) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.371(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.390(5) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 C9 . 1.372(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.490(3) ?
    C10 C12 . 1.531(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.528(3) ?
    C12 C13 . 1.517(3) ?
    C12 H12 . 0.9800 ?
    C14 C15 . 1.394(3) ?
    C14 C19 . 1.406(3) ?
    C15 C16 . 1.374(3) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.385(3) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.379(3) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.394(3) ?
    C18 H18 . 0.9300 ?
    C20 H20A . 0.9600 ?
    C20 H20B . 0.9600 ?
    C20 H20C . 0.9600 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
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
    C8 N1 N2 . . 111.21(19) ?
    C8 N1 C7 . . 129.2(2) ?
    N2 N1 C7 . . 119.6(2) ?
    N3 N2 N1 . . 106.65(19) ?
    N2 N3 C9 . . 109.22(18) ?
    C11 N4 C19 . . 123.05(17) ?
    C11 N4 C20 . . 117.89(17) ?
    C19 N4 C20 . . 119.06(17) ?
    C13 N5 C14 . . 122.66(19) ?
    C13 N5 C21 . . 116.48(19) ?
    C14 N5 C21 . . 118.77(18) ?
    C6 C1 C2 . . 118.8(3) ?
    C6 C1 C7 . . 120.7(3) ?
    C2 C1 C7 . . 120.4(2) ?
    C3 C2 C1 . . 120.4(3) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C4 C3 C2 . . 120.4(3) ?
    C4 C3 H3 . . 119.8 ?
    C2 C3 H3 . . 119.8 ?
    C3 C4 C5 . . 120.7(3) ?
    C3 C4 H4 . . 119.7 ?
    C5 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 119.4(3) ?
    C4 C5 H5 . . 120.3 ?
    C6 C5 H5 . . 120.3 ?
    C1 C6 C5 . . 120.3(3) ?
    C1 C6 H6 . . 119.9 ?
    C5 C6 H6 . . 119.9 ?
    N1 C7 C1 . . 112.38(19) ?
    N1 C7 H7A . . 109.1 ?
    C1 C7 H7A . . 109.1 ?
    N1 C7 H7B . . 109.1 ?
    C1 C7 H7B . . 109.1 ?
    H7A C7 H7B . . 107.9 ?
    N1 C8 C9 . . 105.3(2) ?
    N1 C8 H8 . . 127.4 ?
    C9 C8 H8 . . 127.4 ?
    N3 C9 C8 . . 107.7(2) ?
    N3 C9 C10 . . 122.0(2) ?
    C8 C9 C10 . . 130.3(2) ?
    C9 C10 C12 . . 112.07(18) ?
    C9 C10 H10A . . 109.2 ?
    C12 C10 H10A . . 109.2 ?
    C9 C10 H10B . . 109.2 ?
    C12 C10 H10B . . 109.2 ?
    H10A C10 H10B . . 107.9 ?
    O1 C11 N4 . . 122.12(19) ?
    O1 C11 C12 . . 122.85(19) ?
    N4 C11 C12 . . 115.00(18) ?
    C13 C12 C11 . . 105.92(18) ?
    C13 C12 C10 . . 112.28(18) ?
    C11 C12 C10 . . 111.64(17) ?
    C13 C12 H12 . . 109.0 ?
    C11 C12 H12 . . 109.0 ?
    C10 C12 H12 . . 109.0 ?
    O2 C13 N5 . . 121.9(2) ?
    O2 C13 C12 . . 122.3(2) ?
    N5 C13 C12 . . 115.6(2) ?
    C15 C14 C19 . . 118.5(2) ?
    C15 C14 N5 . . 119.6(2) ?
    C19 C14 N5 . . 121.94(19) ?
    C16 C15 C14 . . 121.4(2) ?
    C16 C15 H15 . . 119.3 ?
    C14 C15 H15 . . 119.3 ?
    C15 C16 C17 . . 120.2(2) ?
    C15 C16 H16 . . 119.9 ?
    C17 C16 H16 . . 119.9 ?
    C18 C17 C16 . . 119.3(2) ?
    C18 C17 H17 . . 120.4 ?
    C16 C17 H17 . . 120.4 ?
    C17 C18 C19 . . 121.4(2) ?
    C17 C18 H18 . . 119.3 ?
    C19 C18 H18 . . 119.3 ?
    C18 C19 C14 . . 119.15(19) ?
    C18 C19 N4 . . 119.24(19) ?
    C14 C19 N4 . . 121.60(19) ?
    N4 C20 H20A . . 109.5 ?
    N4 C20 H20B . . 109.5 ?
    H20A C20 H20B . . 109.5 ?
    N4 C20 H20C . . 109.5 ?
    H20A C20 H20C . . 109.5 ?
    H20B C20 H20C . . 109.5 ?
    N5 C21 H21A . . 109.5 ?
    N5 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    N5 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 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
    C8 N1 N2 N3 . . . . -0.3(2) ?
    C7 N1 N2 N3 . . . . 179.89(18) ?
    N1 N2 N3 C9 . . . . 0.0(2) ?
    C6 C1 C2 C3 . . . . 0.4(3) ?
    C7 C1 C2 C3 . . . . 179.0(2) ?
    C1 C2 C3 C4 . . . . -0.2(4) ?
    C2 C3 C4 C5 . . . . -0.9(5) ?
    C3 C4 C5 C6 . . . . 1.8(5) ?
    C2 C1 C6 C5 . . . . 0.5(4) ?
    C7 C1 C6 C5 . . . . -178.1(2) ?
    C4 C5 C6 C1 . . . . -1.6(5) ?
    C8 N1 C7 C1 . . . . 110.1(3) ?
    N2 N1 C7 C1 . . . . -70.1(3) ?
    C6 C1 C7 N1 . . . . 100.6(3) ?
    C2 C1 C7 N1 . . . . -78.0(3) ?
    N2 N1 C8 C9 . . . . 0.5(2) ?
    C7 N1 C8 C9 . . . . -179.7(2) ?
    N2 N3 C9 C8 . . . . 0.3(2) ?
    N2 N3 C9 C10 . . . . 178.56(19) ?
    N1 C8 C9 N3 . . . . -0.5(2) ?
    N1 C8 C9 C10 . . . . -178.5(2) ?
    N3 C9 C10 C12 . . . . -56.4(3) ?
    C8 C9 C10 C12 . . . . 121.4(2) ?
    C19 N4 C11 O1 . . . . -176.2(2) ?
    C20 N4 C11 O1 . . . . 4.7(3) ?
    C19 N4 C11 C12 . . . . 1.9(3) ?
    C20 N4 C11 C12 . . . . -177.20(19) ?
    O1 C11 C12 C13 . . . . 101.1(2) ?
    N4 C11 C12 C13 . . . . -76.9(2) ?
    O1 C11 C12 C10 . . . . -21.4(3) ?
    N4 C11 C12 C10 . . . . 160.55(19) ?
    C9 C10 C12 C13 . . . . 178.25(18) ?
    C9 C10 C12 C11 . . . . -63.0(2) ?
    C14 N5 C13 O2 . . . . -170.7(2) ?
    C21 N5 C13 O2 . . . . -7.4(3) ?
    C14 N5 C13 C12 . . . . 12.8(3) ?
    C21 N5 C13 C12 . . . . 176.14(18) ?
    C11 C12 C13 O2 . . . . -109.6(2) ?
    C10 C12 C13 O2 . . . . 12.5(3) ?
    C11 C12 C13 N5 . . . . 66.9(2) ?
    C10 C12 C13 N5 . . . . -171.04(18) ?
    C13 N5 C14 C15 . . . . 130.3(2) ?
    C21 N5 C14 C15 . . . . -32.6(3) ?
    C13 N5 C14 C19 . . . . -50.9(3) ?
    C21 N5 C14 C19 . . . . 146.1(2) ?
    C19 C14 C15 C16 . . . . 3.0(3) ?
    N5 C14 C15 C16 . . . . -178.2(2) ?
    C14 C15 C16 C17 . . . . 0.4(4) ?
    C15 C16 C17 C18 . . . . -2.4(4) ?
    C16 C17 C18 C19 . . . . 1.0(3) ?
    C17 C18 C19 C14 . . . . 2.4(3) ?
    C17 C18 C19 N4 . . . . -176.7(2) ?
    C15 C14 C19 C18 . . . . -4.3(3) ?
    N5 C14 C19 C18 . . . . 176.90(19) ?
    C15 C14 C19 N4 . . . . 174.74(18) ?
    N5 C14 C19 N4 . . . . -4.0(3) ?
    C11 N4 C19 C18 . . . . -132.9(2) ?
    C20 N4 C19 C18 . . . . 46.1(3) ?
    C11 N4 C19 C14 . . . . 48.0(3) ?
    C20 N4 C19 C14 . . . . -132.9(2) ?