##############################################################################
###                                                                        ###
###        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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#                                                                            #
# 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
_chemical_name_systematic
;
4-(Piperidin-1-yl)-4H-benzo[b]tetrazolo[1,5-
d][1,4]diazepin-5(6H)-one
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H16 N6 O'
_chemical_formula_sum     'C14 H16 N6 O'
_chemical_formula_iupac     'C14 H16 N6 O'
_chemical_formula_weight     284.33
_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     8.8210(7)
_cell_length_b     13.1802(10)
_cell_length_c     13.4476(11)
_cell_angle_alpha     105.549(2)
_cell_angle_beta     99.490(2)
_cell_angle_gamma     106.623(2)
_cell_volume     1392.99(19)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9970
_cell_measurement_theta_min     2.49
_cell_measurement_theta_max     35.54
_cell_measurement_temperature     100(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.39
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.09
_exptl_crystal_density_diffrn     1.356
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     600
_exptl_absorpt_coefficient_mu     0.092
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9648
_exptl_absorpt_correction_T_max     0.9916
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     51078
_diffrn_reflns_av_R_equivalents     0.0292
_diffrn_reflns_av_sigmaI/netI     0.0274
_diffrn_reflns_theta_min     1.63
_diffrn_reflns_theta_max     34.97
_diffrn_reflns_theta_full     34.97
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -21
_diffrn_reflns_limit_k_max     21
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     19
_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     12177
_reflns_number_gt     9733
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0571
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.1134
_refine_ls_wR_factor_ref     0.1232
_refine_ls_goodness_of_fit_ref     1.048
_refine_ls_restrained_S_all     1.048
_refine_ls_number_reflns     12177
_refine_ls_number_parameters     507
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0711P)²+0.1991P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     difmap
_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     0.594
_refine_diff_density_min     -0.227
_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, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and
Mercury (Macrae et al. 2008)
;
_computing_publication_material
                                  'SHELXTL (Sheldrick, 2008) and local programs'
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 0.38761(7) 0.05350(5) 0.43124(5) 0.01571(11) Uani d . 1 . .
    N N1 0.60561(8) 0.01832(6) 0.38204(5) 0.01320(11) Uani d . 1 . .
    H H1N 0.6179(16) -0.0054(11) 0.4346(11) 0.022(3) Uiso d . 1 . .
    N N2 0.28444(8) -0.02275(6) 0.10021(5) 0.01491(11) Uani d . 1 . .
    N N3 0.31273(9) -0.10081(6) 0.02234(5) 0.01668(12) Uani d . 1 . .
    N N4 0.45718(9) -0.10612(6) 0.05193(5) 0.01538(12) Uani d . 1 . .
    N N5 0.52683(8) -0.02989(5) 0.15250(5) 0.01189(10) Uani d . 1 . .
    N N6 0.60485(8) 0.20364(5) 0.29571(5) 0.01251(11) Uani d . 1 . .
    C C1 0.48112(9) 0.05928(6) 0.37255(6) 0.01170(11) Uani d . 1 . .
    C C2 0.45700(9) 0.11124(6) 0.28435(6) 0.01159(11) Uani d . 1 . .
    H H2 0.3595(15) 0.1330(10) 0.2855(10) 0.017(3) Uiso d . 1 . .
    C C3 0.41921(9) 0.02050(6) 0.17984(6) 0.01156(11) Uani d . 1 . .
    C C4 0.68763(9) -0.01103(6) 0.21140(6) 0.01208(12) Uani d . 1 . .
    C C5 0.80602(10) -0.02132(7) 0.15637(7) 0.01617(13) Uani d . 1 . .
    H H5 0.7760(17) -0.0426(12) 0.0765(11) 0.027(3) Uiso d . 1 . .
    C C6 0.96362(10) -0.00308(7) 0.21295(7) 0.01873(14) Uani d . 1 . .
    H H6 1.0457(18) -0.0093(12) 0.1781(12) 0.030(3) Uiso d . 1 . .
    C C7 1.00262(10) 0.02641(7) 0.32418(7) 0.01900(14) Uani d . 1 . .
    H H7 1.1107(19) 0.0416(12) 0.3635(12) 0.033(4) Uiso d . 1 . .
    C C8 0.88362(9) 0.03591(7) 0.37831(7) 0.01614(13) Uani d . 1 . .
    H H8 0.9081(16) 0.0536(11) 0.4581(11) 0.022(3) Uiso d . 1 . .
    C C9 0.72383(9) 0.01681(6) 0.32280(6) 0.01220(12) Uani d . 1 . .
    C C10 0.57954(10) 0.25511(7) 0.21242(6) 0.01617(13) Uani d . 1 . .
    H H10A 0.5286(16) 0.1938(11) 0.1401(11) 0.023(3) Uiso d . 1 . .
    H H10B 0.4961(17) 0.2921(11) 0.2234(11) 0.025(3) Uiso d . 1 . .
    C C11 0.74158(12) 0.33854(7) 0.21560(8) 0.02248(16) Uani d . 1 . .
    H H11A 0.8144(18) 0.2980(13) 0.1966(12) 0.033(4) Uiso d . 1 . .
    H H11 0.722(2) 0.3742(13) 0.1604(13) 0.040(4) Uiso d . 1 . .
    C C12 0.81799(14) 0.42864(8) 0.32592(9) 0.02767(19) Uani d . 1 . .
    H H12A 0.753(2) 0.4792(14) 0.3395(13) 0.039(4) Uiso d . 1 . .
    H H12B 0.933(2) 0.4793(14) 0.3300(13) 0.039(4) Uiso d . 1 . .
    C C13 0.82547(12) 0.37556(8) 0.41398(8) 0.02422(17) Uani d . 1 . .
    H H13A 0.9033(18) 0.3335(12) 0.4088(12) 0.031(4) Uiso d . 1 . .
    H H13B 0.8589(17) 0.4330(12) 0.4846(11) 0.027(3) Uiso d . 1 . .
    C C14 0.65953(10) 0.28969(7) 0.40202(6) 0.01774(14) Uani d . 1 . .
    H H14A 0.6707(17) 0.2514(11) 0.4561(11) 0.026(3) Uiso d . 1 . .
    H H14B 0.5794(18) 0.3278(12) 0.4109(11) 0.029(3) Uiso d . 1 . .
    O O51 0.52486(10) 0.64389(6) 0.05346(5) 0.02384(13) Uani d . 1 . .
    N N51 0.40757(10) 0.50343(6) 0.11293(6) 0.01766(13) Uani d . 1 . .
    H H51N 0.4212(19) 0.4560(13) 0.0574(13) 0.036(4) Uiso d . 1 . .
    N N52 0.67271(10) 0.77756(6) 0.37934(6) 0.02130(14) Uani d . 1 . .
    N N53 0.72173(10) 0.73295(7) 0.45426(6) 0.02402(15) Uani d . 1 . .
    N N54 0.62468(10) 0.63061(7) 0.43334(6) 0.02147(14) Uani d . 1 . .
    N N55 0.50786(9) 0.60616(6) 0.34204(5) 0.01671(12) Uani d . 1 . .
    N N56 0.26638(9) 0.67324(6) 0.22010(5) 0.01605(12) Uani d . 1 . .
    C C51 0.45755(11) 0.61293(7) 0.11881(6) 0.01729(14) Uani d . 1 . .
    C C52 0.43580(10) 0.69955(6) 0.21216(6) 0.01637(13) Uani d . 1 . .
    H H52 0.4837(16) 0.7759(11) 0.2025(10) 0.020(3) Uiso d . 1 . .
    C C53 0.53997(10) 0.69786(7) 0.31100(6) 0.01685(13) Uani d . 1 . .
    C C54 0.38196(10) 0.49889(6) 0.29242(6) 0.01599(13) Uani d . 1 . .
    C C55 0.31368(11) 0.44075(7) 0.35588(7) 0.01975(15) Uani d . 1 . .
    H H55 0.3508(16) 0.4735(11) 0.4336(11) 0.022(3) Uiso d . 1 . .
    C C56 0.19621(11) 0.33379(8) 0.30809(8) 0.02194(16) Uani d . 1 . .
    H H56 0.1541(17) 0.2909(12) 0.3505(11) 0.027(3) Uiso d . 1 . .
    C C57 0.14557(11) 0.28606(7) 0.19694(8) 0.02214(16) Uani d . 1 . .
    H H57 0.0629(17) 0.2098(12) 0.1595(12) 0.029(3) Uiso d . 1 . .
    C C58 0.21359(11) 0.34480(7) 0.13379(7) 0.01951(15) Uani d . 1 . .
    H H58 0.1781(17) 0.3104(12) 0.0555(11) 0.027(3) Uiso d . 1 . .
    C C59 0.33285(10) 0.45203(6) 0.18068(6) 0.01597(13) Uani d . 1 . .
    C C60 0.14703(12) 0.64876(7) 0.11863(7) 0.02103(15) Uani d . 1 . .
    H H60 0.1632(16) 0.7177(11) 0.1003(11) 0.023(3) Uiso d . 1 . .
    H H60B 0.1633(17) 0.5889(12) 0.0625(11) 0.028(3) Uiso d . 1 . .
    C C61 -0.02563(12) 0.60567(8) 0.13221(8) 0.02450(17) Uani d . 1 . .
    H H61A -0.1061(19) 0.5883(13) 0.0638(13) 0.038(4) Uiso d . 1 . .
    H H61B -0.0431(17) 0.5330(12) 0.1488(11) 0.027(3) Uiso d . 1 . .
    C C62 -0.05395(13) 0.69164(9) 0.22197(9) 0.0310(2) Uani d . 1 . .
    H H62A -0.059(2) 0.7574(15) 0.1989(14) 0.049(5) Uiso d . 1 . .
    H H62B -0.164(2) 0.6604(14) 0.2299(13) 0.039(4) Uiso d . 1 . .
    C C63 0.08227(13) 0.73000(9) 0.32478(8) 0.02806(19) Uani d . 1 . .
    H H63A 0.075(2) 0.6703(14) 0.3558(13) 0.039(4) Uiso d . 1 . .
    H H63B 0.0736(19) 0.7914(13) 0.3791(13) 0.038(4) Uiso d . 1 . .
    C C64 0.25074(11) 0.76573(7) 0.30339(7) 0.02088(15) Uani d . 1 . .
    H H64A 0.3370(17) 0.7863(11) 0.3681(11) 0.025(3) Uiso d . 1 . .
    H H64B 0.2700(17) 0.8337(12) 0.2788(11) 0.030(3) 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
    O1 C1 . 1.2329(9) ?
    N1 H1N . 0.850(14) ?
    N1 C1 . 1.3578(9) ?
    N1 C9 . 1.4142(10) ?
    N2 N3 . 1.3686(10) ?
    N2 C3 . 1.3229(9) ?
    N3 N4 . 1.2983(10) ?
    N4 N5 . 1.3640(9) ?
    N5 C3 . 1.3499(9) ?
    N5 C4 . 1.4225(9) ?
    N6 C2 . 1.4605(10) ?
    N6 C10 . 1.4752(10) ?
    N6 C14 . 1.4674(10) ?
    C1 C2 . 1.5351(10) ?
    C2 H2 . 0.982(12) ?
    C2 C3 . 1.4944(10) ?
    C4 C5 . 1.3923(10) ?
    C4 C9 . 1.4004(10) ?
    C5 H5 . 1.002(14) ?
    C5 C6 . 1.3897(11) ?
    C6 H6 . 0.936(15) ?
    C6 C7 . 1.3959(13) ?
    C7 H7 . 0.947(15) ?
    C7 C8 . 1.3877(12) ?
    C8 H8 . 1.007(13) ?
    C8 C9 . 1.3988(10) ?
    C10 H10A . 1.014(13) ?
    C10 H10B . 1.001(14) ?
    C10 C11 . 1.5196(12) ?
    C11 H11A . 0.969(15) ?
    C11 H11 . 0.996(16) ?
    C11 C12 . 1.5275(14) ?
    C12 H12A . 0.996(16) ?
    C12 H12B . 1.023(16) ?
    C12 C13 . 1.5300(15) ?
    C13 H13A . 0.998(15) ?
    C13 H13B . 0.979(14) ?
    C13 C14 . 1.5252(12) ?
    C14 H14A . 0.998(14) ?
    C14 H14B . 0.982(14) ?
    O51 C51 . 1.2317(10) ?
    N51 H51N . 0.886(16) ?
    N51 C51 . 1.3589(10) ?
    N51 C59 . 1.4131(11) ?
    N52 N53 . 1.3663(11) ?
    N52 C53 . 1.3202(11) ?
    N53 N54 . 1.2992(12) ?
    N54 N55 . 1.3615(10) ?
    N55 C53 . 1.3524(11) ?
    N55 C54 . 1.4244(11) ?
    N56 C52 . 1.4632(11) ?
    N56 C60 . 1.4731(11) ?
    N56 C64 . 1.4748(11) ?
    C51 C52 . 1.5338(11) ?
    C52 H52 . 1.026(13) ?
    C52 C53 . 1.4955(11) ?
    C54 C55 . 1.3908(11) ?
    C54 C59 . 1.4005(11) ?
    C55 H55 . 0.974(13) ?
    C55 C56 . 1.3904(13) ?
    C56 H56 . 0.951(14) ?
    C56 C57 . 1.3943(14) ?
    C57 H57 . 0.992(14) ?
    C57 C58 . 1.3912(13) ?
    C58 H58 . 0.983(14) ?
    C58 C59 . 1.3982(12) ?
    C60 H60 . 0.982(13) ?
    C60 H60B . 0.997(14) ?
    C60 C61 . 1.5258(14) ?
    C61 H61A . 0.991(16) ?
    C61 H61B . 1.016(14) ?
    C61 C62 . 1.5269(14) ?
    C62 H62A . 1.005(18) ?
    C62 H62B . 0.974(17) ?
    C62 C63 . 1.5300(16) ?
    C63 H63A . 0.977(16) ?
    C63 H63B . 0.965(16) ?
    C63 C64 . 1.5252(14) ?
    C64 H64A . 0.973(14) ?
    C64 H64B . 1.015(14) ?
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
    H1N N1 C1 . . 114.3(9) ?
    H1N N1 C9 . . 115.7(9) ?
    C1 N1 C9 . . 129.81(6) ?
    N3 N2 C3 . . 105.55(6) ?
    N2 N3 N4 . . 111.36(6) ?
    N3 N4 N5 . . 106.08(6) ?
    N4 N5 C3 . . 108.10(6) ?
    N4 N5 C4 . . 122.45(6) ?
    C3 N5 C4 . . 129.44(6) ?
    C2 N6 C10 . . 111.02(6) ?
    C2 N6 C14 . . 112.06(6) ?
    C10 N6 C14 . . 109.94(6) ?
    O1 C1 N1 . . 121.56(7) ?
    O1 C1 C2 . . 120.43(6) ?
    N1 C1 C2 . . 118.00(6) ?
    N6 C2 C1 . . 111.27(6) ?
    N6 C2 H2 . . 113.6(7) ?
    N6 C2 C3 . . 109.40(6) ?
    C1 C2 H2 . . 108.1(7) ?
    C1 C2 C3 . . 107.10(6) ?
    H2 C2 C3 . . 107.0(7) ?
    N2 C3 N5 . . 108.91(6) ?
    N2 C3 C2 . . 128.45(7) ?
    N5 C3 C2 . . 122.63(6) ?
    N5 C4 C5 . . 118.89(7) ?
    N5 C4 C9 . . 119.78(6) ?
    C5 C4 C9 . . 121.33(7) ?
    C4 C5 H5 . . 119.5(8) ?
    C4 C5 C6 . . 119.48(7) ?
    H5 C5 C6 . . 121.0(8) ?
    C5 C6 H6 . . 121.3(9) ?
    C5 C6 C7 . . 119.99(7) ?
    H6 C6 C7 . . 118.7(9) ?
    C6 C7 H7 . . 120.5(9) ?
    C6 C7 C8 . . 120.13(7) ?
    H7 C7 C8 . . 119.4(9) ?
    C7 C8 H8 . . 121.2(8) ?
    C7 C8 C9 . . 120.79(7) ?
    H8 C8 C9 . . 118.0(8) ?
    N1 C9 C4 . . 123.90(6) ?
    N1 C9 C8 . . 117.64(7) ?
    C4 C9 C8 . . 118.27(7) ?
    N6 C10 H10A . . 109.2(7) ?
    N6 C10 H10B . . 109.5(8) ?
    N6 C10 C11 . . 109.81(7) ?
    H10A C10 H10B . . 105.0(11) ?
    H10A C10 C11 . . 111.8(8) ?
    H10B C10 C11 . . 111.4(8) ?
    C10 C11 H11A . . 108.7(9) ?
    C10 C11 H11 . . 108.8(9) ?
    C10 C11 C12 . . 110.94(8) ?
    H11A C11 H11 . . 107.3(13) ?
    H11A C11 C12 . . 111.0(9) ?
    H11 C11 C12 . . 109.9(9) ?
    C11 C12 H12A . . 110.7(9) ?
    C11 C12 H12B . . 110.5(9) ?
    C11 C12 C13 . . 110.97(8) ?
    H12A C12 H12B . . 105.6(13) ?
    H12A C12 C13 . . 108.5(9) ?
    H12B C12 C13 . . 110.4(9) ?
    C12 C13 H13A . . 110.2(9) ?
    C12 C13 H13B . . 110.7(8) ?
    C12 C13 C14 . . 111.35(8) ?
    H13A C13 H13B . . 110.0(12) ?
    H13A C13 C14 . . 106.0(8) ?
    H13B C13 C14 . . 108.4(8) ?
    N6 C14 C13 . . 109.53(7) ?
    N6 C14 H14A . . 107.6(8) ?
    N6 C14 H14B . . 109.8(8) ?
    C13 C14 H14A . . 109.5(8) ?
    C13 C14 H14B . . 109.4(8) ?
    H14A C14 H14B . . 111.0(12) ?
    H51N N51 C51 . . 115.8(10) ?
    H51N N51 C59 . . 114.1(10) ?
    C51 N51 C59 . . 130.00(7) ?
    N53 N52 C53 . . 105.52(7) ?
    N52 N53 N54 . . 111.29(7) ?
    N53 N54 N55 . . 106.29(7) ?
    N54 N55 C53 . . 107.76(7) ?
    N54 N55 C54 . . 122.40(7) ?
    C53 N55 C54 . . 129.82(7) ?
    C52 N56 C60 . . 113.57(7) ?
    C52 N56 C64 . . 110.57(6) ?
    C60 N56 C64 . . 109.24(7) ?
    O51 C51 N51 . . 121.40(7) ?
    O51 C51 C52 . . 119.90(7) ?
    N51 C51 C52 . . 118.64(7) ?
    N56 C52 C51 . . 113.38(7) ?
    N56 C52 H52 . . 113.6(7) ?
    N56 C52 C53 . . 108.84(7) ?
    C51 C52 H52 . . 105.9(7) ?
    C51 C52 C53 . . 105.63(6) ?
    H52 C52 C53 . . 109.1(7) ?
    N52 C53 N55 . . 109.13(7) ?
    N52 C53 C52 . . 128.94(8) ?
    N55 C53 C52 . . 121.92(7) ?
    N55 C54 C55 . . 119.38(7) ?
    N55 C54 C59 . . 119.52(7) ?
    C55 C54 C59 . . 121.06(8) ?
    C54 C55 H55 . . 120.3(8) ?
    C54 C55 C56 . . 119.71(8) ?
    H55 C55 C56 . . 119.9(8) ?
    C55 C56 H56 . . 120.7(9) ?
    C55 C56 C57 . . 119.95(8) ?
    H56 C56 C57 . . 119.3(9) ?
    C56 C57 H57 . . 122.7(8) ?
    C56 C57 C58 . . 120.12(8) ?
    H57 C57 C58 . . 117.2(8) ?
    C57 C58 H58 . . 119.8(8) ?
    C57 C58 C59 . . 120.60(8) ?
    H58 C58 C59 . . 119.6(8) ?
    N51 C59 C54 . . 123.27(7) ?
    N51 C59 C58 . . 117.95(7) ?
    C54 C59 C58 . . 118.55(7) ?
    N56 C60 H60 . . 109.4(8) ?
    N56 C60 H60B . . 108.1(8) ?
    N56 C60 C61 . . 108.76(7) ?
    H60 C60 H60B . . 111.6(11) ?
    H60 C60 C61 . . 109.8(8) ?
    H60B C60 C61 . . 109.2(8) ?
    C60 C61 H61A . . 108.9(9) ?
    C60 C61 H61B . . 109.5(8) ?
    C60 C61 C62 . . 111.39(8) ?
    H61A C61 H61B . . 107.4(12) ?
    H61A C61 C62 . . 110.2(9) ?
    H61B C61 C62 . . 109.4(8) ?
    C61 C62 H62A . . 109.2(10) ?
    C61 C62 H62B . . 109.1(9) ?
    C61 C62 C63 . . 110.61(8) ?
    H62A C62 H62B . . 102.9(13) ?
    H62A C62 C63 . . 110.7(10) ?
    H62B C62 C63 . . 114.0(9) ?
    C62 C63 H63A . . 111.7(10) ?
    C62 C63 H63B . . 111.2(9) ?
    C62 C63 C64 . . 110.88(9) ?
    H63A C63 H63B . . 105.8(13) ?
    H63A C63 C64 . . 107.8(9) ?
    H63B C63 C64 . . 109.4(9) ?
    N56 C64 C63 . . 110.32(7) ?
    N56 C64 H64A . . 108.6(8) ?
    N56 C64 H64B . . 108.5(8) ?
    C63 C64 H64A . . 110.7(8) ?
    C63 C64 H64B . . 111.4(8) ?
    H64A C64 H64B . . 107.2(12) ?
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
    C3 N2 N3 N4 . . . . 0.15(9) ?
    N2 N3 N4 N5 . . . . 0.29(8) ?
    N3 N4 N5 C3 . . . . -0.62(8) ?
    N3 N4 N5 C4 . . . . -179.48(7) ?
    C9 N1 C1 O1 . . . . 179.78(7) ?
    C9 N1 C1 C2 . . . . 1.11(11) ?
    C10 N6 C2 C1 . . . . -178.53(6) ?
    C10 N6 C2 C3 . . . . 63.32(7) ?
    C14 N6 C2 C1 . . . . -55.17(8) ?
    C14 N6 C2 C3 . . . . -173.31(6) ?
    O1 C1 C2 N6 . . . . 123.80(7) ?
    O1 C1 C2 C3 . . . . -116.68(7) ?
    N1 C1 C2 N6 . . . . -57.52(8) ?
    N1 C1 C2 C3 . . . . 62.01(8) ?
    N3 N2 C3 N5 . . . . -0.53(8) ?
    N3 N2 C3 C2 . . . . 178.55(7) ?
    N4 N5 C3 N2 . . . . 0.73(8) ?
    N4 N5 C3 C2 . . . . -178.43(6) ?
    C4 N5 C3 N2 . . . . 179.49(7) ?
    C4 N5 C3 C2 . . . . 0.33(12) ?
    N6 C2 C3 N2 . . . . -121.66(8) ?
    N6 C2 C3 N5 . . . . 57.31(9) ?
    C1 C2 C3 N2 . . . . 117.62(8) ?
    C1 C2 C3 N5 . . . . -63.41(9) ?
    N4 N5 C4 C5 . . . . 33.23(10) ?
    N4 N5 C4 C9 . . . . -146.46(7) ?
    C3 N5 C4 C5 . . . . -145.37(8) ?
    C3 N5 C4 C9 . . . . 34.94(11) ?
    N5 C4 C5 C6 . . . . 179.98(7) ?
    C9 C4 C5 C6 . . . . -0.34(12) ?
    C4 C5 C6 C7 . . . . -0.64(12) ?
    C5 C6 C7 C8 . . . . 0.98(13) ?
    C6 C7 C8 C9 . . . . -0.34(13) ?
    C7 C8 C9 N1 . . . . 174.59(7) ?
    C7 C8 C9 C4 . . . . -0.62(11) ?
    N5 C4 C9 N1 . . . . 5.76(11) ?
    N5 C4 C9 C8 . . . . -179.36(7) ?
    C5 C4 C9 N1 . . . . -173.92(7) ?
    C5 C4 C9 C8 . . . . 0.96(11) ?
    C1 N1 C9 C4 . . . . -43.24(12) ?
    C1 N1 C9 C8 . . . . 141.84(8) ?
    C2 N6 C10 C11 . . . . -171.45(6) ?
    C14 N6 C10 C11 . . . . 63.98(8) ?
    N6 C10 C11 C12 . . . . -57.34(10) ?
    C10 C11 C12 C13 . . . . 50.96(11) ?
    C11 C12 C13 C14 . . . . -50.81(11) ?
    C2 N6 C14 C13 . . . . 172.62(7) ?
    C10 N6 C14 C13 . . . . -63.41(9) ?
    C12 C13 C14 N6 . . . . 56.84(10) ?
    C53 N52 N53 N54 . . . . 0.19(10) ?
    N52 N53 N54 N55 . . . . 0.05(10) ?
    N53 N54 N55 C53 . . . . -0.27(9) ?
    N53 N54 N55 C54 . . . . 177.97(8) ?
    C59 N51 C51 O51 . . . . 178.22(9) ?
    C59 N51 C51 C52 . . . . 0.99(14) ?
    C60 N56 C52 C51 . . . . -50.44(9) ?
    C60 N56 C52 C53 . . . . -167.67(6) ?
    C64 N56 C52 C51 . . . . -173.65(7) ?
    C64 N56 C52 C53 . . . . 69.12(8) ?
    O51 C51 C52 N56 . . . . 126.51(9) ?
    O51 C51 C52 C53 . . . . -114.40(9) ?
    N51 C51 C52 N56 . . . . -56.22(10) ?
    N51 C51 C52 C53 . . . . 62.87(10) ?
    N53 N52 C53 N55 . . . . -0.36(9) ?
    N53 N52 C53 C52 . . . . -179.19(8) ?
    N54 N55 C53 N52 . . . . 0.40(9) ?
    N54 N55 C53 C52 . . . . 179.32(7) ?
    C54 N55 C53 N52 . . . . -177.66(8) ?
    C54 N55 C53 C52 . . . . 1.26(13) ?
    N56 C52 C53 N52 . . . . -124.11(9) ?
    N56 C52 C53 N55 . . . . 57.19(10) ?
    C51 C52 C53 N52 . . . . 113.82(9) ?
    C51 C52 C53 N55 . . . . -64.87(10) ?
    N54 N55 C54 C55 . . . . 36.85(11) ?
    N54 N55 C54 C59 . . . . -140.99(8) ?
    C53 N55 C54 C55 . . . . -145.34(9) ?
    C53 N55 C54 C59 . . . . 36.82(12) ?
    N55 C54 C55 C56 . . . . -177.01(8) ?
    C59 C54 C55 C56 . . . . 0.80(13) ?
    C54 C55 C56 C57 . . . . -0.99(13) ?
    C55 C56 C57 C58 . . . . 0.65(14) ?
    C56 C57 C58 C59 . . . . -0.11(14) ?
    C57 C58 C59 N51 . . . . 174.60(8) ?
    C57 C58 C59 C54 . . . . -0.09(13) ?
    N55 C54 C59 N51 . . . . 3.16(12) ?
    N55 C54 C59 C58 . . . . 177.55(7) ?
    C55 C54 C59 N51 . . . . -174.65(8) ?
    C55 C54 C59 C58 . . . . -0.26(12) ?
    C51 N51 C59 C54 . . . . -41.97(13) ?
    C51 N51 C59 C58 . . . . 143.61(9) ?
    C52 N56 C60 C61 . . . . 171.56(7) ?
    C64 N56 C60 C61 . . . . -64.50(9) ?
    N56 C60 C61 C62 . . . . 58.95(10) ?
    C60 C61 C62 C63 . . . . -52.02(12) ?
    C61 C62 C63 C64 . . . . 50.42(12) ?
    C52 N56 C64 C63 . . . . -170.26(8) ?
    C60 N56 C64 C63 . . . . 64.06(10) ?
    C62 C63 C64 N56 . . . . -56.70(11) ?
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 H1N O1 2_656 0.850(14) 2.069(14) 2.9089(9) 169.4(13) y
    N51 H51N O51 2_665 0.886(16) 1.929(16) 2.8116(10) 173.6(14) y
    C6 H6 N2 1_655 0.936(15) 2.531(15) 3.4638(11) 174.8(12) y
    C7 H7 O1 1_655 0.947(15) 2.406(15) 3.3394(10) 168.4(13) y
    C55 H55 N54 2_666 0.974(13) 2.548(13) 3.2293(11) 127.0(10) y
data_global
_journal_date_recd_electronic     2010-11-15
_journal_date_accepted     2010-11-29
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue      1
_journal_page_first     o23
_journal_page_last     o24
_journal_paper_category     QO
_journal_coeditor_code     KJ2167
_publ_contact_author_name     'Gary S. Nichol'
_publ_contact_author_address
;
Department of Chemistry and Biochemistry
1306 E University Boulevard
The University of Arizona
Tucson, AZ 85721
United States of America
;
_publ_contact_author_email     'gsnichol@email.arizona.edu'
_publ_contact_author_fax     '+1 520 621 4168'
_publ_contact_author_phone     '+1 520 621 4168'
_publ_section_title
;\
4-(Piperidin-1-yl)-4H-benzo[b]tetrazolo[1,5-d][1,4]\
diazepin-5(6H)-one
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Nichol, Gary S.' ?
;
Department of Chemistry and Biochemistry
1306 E University Boulevard
The University of Arizona
Tucson, AZ 85721
USA
;
    'Xu, Zhigang' .
;
Southwest Center for Drug
Discovery and Development
College of Pharmacy
BIO5 Institute
The University of Arizona
Tucson, AZ 85721
USA
;
    'Kaiser, Christine E.' .
;
Southwest Center for Drug
Discovery and Development
College of Pharmacy
BIO5 Institute
The University of Arizona
Tucson, AZ 85721
USA
;
    'Hulme, Christopher' .
;
Southwest Center for Drug
Discovery and Development
College of Pharmacy
BIO5 Institute
The University of Arizona
Tucson, AZ 85721
USA
;
