#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/87/2228793.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2228793
loop_
_publ_author_name
'Nichol, Gary S.'
'Xu, Zhigang'
'Kaiser, Christine E.'
'Hulme, Christopher'
_publ_section_title
;
 4-(Piperidin-1-yl)-4H-benzo[b]tetrazolo[1,5-d][1,4]diazepin-5(6H)-one
;
_journal_coeditor_code           KJ2167
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o23
_journal_page_last               o24
_journal_paper_doi               10.1107/S1600536810049950
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C14 H16 N6 O'
_chemical_formula_moiety         'C14 H16 N6 O'
_chemical_formula_sum            'C14 H16 N6 O'
_chemical_formula_weight         284.33
_chemical_name_systematic
;
4-(Piperidin-1-yl)-4H-benzo[b]tetrazolo[1,5-
d][1,4]diazepin-5(6H)-one
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                105.549(2)
_cell_angle_beta                 99.490(2)
_cell_angle_gamma                106.623(2)
_cell_formula_units_Z            4
_cell_length_a                   8.8210(7)
_cell_length_b                   13.1802(10)
_cell_length_c                   13.4476(11)
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.54
_cell_measurement_theta_min      2.49
_cell_volume                     1392.99(19)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 1997) and
Mercury (Macrae et al. 2008)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube with Miracol optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0274
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            51078
_diffrn_reflns_theta_full        34.97
_diffrn_reflns_theta_max         34.97
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.9648
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.227
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     507
_refine_ls_number_reflns         12177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0711P)²+0.1991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                9733
_reflns_number_total             12177
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kj2167.cif
_cod_data_source_block           I
_cod_database_code               2228793
_cod_database_fobs_code          2228793
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 . .
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'
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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139080339
