#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201026.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_2201026
loop_
_publ_author_name
'Näther, Christian'
'Krüger, Oliver'
'Wille, Uta'
_publ_section_title
cis-[4a]-cisoid-[4a,4b]-cis-[4b]-8a,8b-Diethyl-1,3,6,8-tetramethylperhydro-1,3,6,8-tetraazabiphenylene-2,4,5,7-tetraone
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o415
_journal_page_last               o416
_journal_paper_doi               10.1107/S1600536802004506
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C16 H24 N4 O4'
_chemical_formula_moiety         'C16 H24 N4 O4'
_chemical_formula_sum            'C16 H24 N4 O4'
_chemical_formula_weight         336.39
_chemical_name_common
;
cis-[4a]-cisoid-[4a,4b]-cis-[4b]-8a,8b-Diethyl-1,3,6,8-tetramethylperhydro-
1,3,6,8-tetraazabiphenylene-2,4,5,7-tetraone
;
_chemical_name_systematic        ?
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.481(9)
_cell_angle_beta                 101.269(8)
_cell_angle_gamma                90.518(8)
_cell_formula_units_Z            4
_cell_length_a                   8.5284(6)
_cell_length_b                   12.2178(9)
_cell_length_c                   16.2102(12)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      10.5
_cell_volume                     1655.8(2)
_computing_cell_refinement       'IPDS Program Package'
_computing_data_collection       'IPDS Program Package (Stoe & Cie, 1998)'
_computing_data_reduction        'IPDS Program Package'
_computing_molecular_graphics    'XP in SHELXTL (Bruker, 1998)'
_computing_publication_material  'CIFTAB in SHELXL97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Stoe Imaging Plate Diffraction System'
_diffrn_measurement_method       φ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15745
_diffrn_reflns_theta_full        28.12
_diffrn_reflns_theta_max         28.12
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.313
_refine_ls_extinction_coef       0.035(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7846
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0822P)²+0.1459P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                5552
_reflns_number_total             7846
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6124.cif
_cod_data_source_block           I
_cod_database_code               2201026
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
N1 0.77510(18) 0.95707(11) 0.32436(10) 0.0285(3) Uani d . 1 . . N
C2 0.9282(2) 0.93997(15) 0.36440(12) 0.0325(4) Uani d . 1 . . C
N3 0.97635(17) 0.83147(12) 0.38259(10) 0.0301(3) Uani d . 1 . . N
C4 0.8845(2) 0.74016(13) 0.35502(10) 0.0248(3) Uani d . 1 . . C
C5 0.72079(19) 0.76051(12) 0.30527(10) 0.0230(3) Uani d . 1 . . C
H5 0.6450 0.7032 0.3178 0.028 Uiso calc R 1 . . H
C6 0.64595(19) 0.87469(13) 0.31050(10) 0.0248(3) Uani d . 1 . . C
C11 0.7314(3) 1.07289(15) 0.31682(14) 0.0425(5) Uani d . 1 . . C
H11A 0.7629 1.1105 0.3718 0.064 Uiso calc R 1 . . H
H11B 0.6155 1.0784 0.2974 0.064 Uiso calc R 1 . . H
H11C 0.7866 1.1071 0.2762 0.064 Uiso calc R 1 . . H
O12 1.0243(2) 1.01508(13) 0.38405(12) 0.0524(4) Uani d . 1 . . O
C13 1.1406(2) 0.81515(19) 0.42869(15) 0.0445(5) Uani d . 1 . . C
H13A 1.1379 0.7900 0.4853 0.067 Uiso calc R 1 . . H
H13B 1.2008 0.8845 0.4328 0.067 Uiso calc R 1 . . H
H13C 1.1927 0.7601 0.3986 0.067 Uiso calc R 1 . . H
O14 0.93359(16) 0.64769(10) 0.37032(8) 0.0317(3) Uani d . 1 . . O
C16 0.5336(2) 0.88878(16) 0.37258(11) 0.0319(4) Uani d . 1 . . C
H16A 0.4867 0.9627 0.3669 0.038 Uiso calc R 1 . . H
H16B 0.4450 0.8344 0.3581 0.038 Uiso calc R 1 . . H
C17 0.6175(3) 0.8745(2) 0.46369(12) 0.0436(5) Uani d . 1 . . C
H17A 0.5405 0.8848 0.5008 0.065 Uiso calc R 1 . . H
H17B 0.7042 0.9289 0.4787 0.065 Uiso calc R 1 . . H
H17C 0.6616 0.8008 0.4701 0.065 Uiso calc R 1 . . H
N21 0.57855(18) 0.94924(11) 0.15695(9) 0.0276(3) Uani d . 1 . . N
C22 0.7057(2) 0.97327(13) 0.12154(11) 0.0286(3) Uani d . 1 . . C
N23 0.83927(17) 0.90342(11) 0.13592(9) 0.0263(3) Uani d . 1 . . N
C24 0.8491(2) 0.80843(13) 0.17937(10) 0.0258(3) Uani d . 1 . . C
C25 0.70066(19) 0.77042(12) 0.20801(10) 0.0229(3) Uani d . 1 . . C
H25 0.6539 0.7022 0.1771 0.027 Uiso calc R 1 . . H
C26 0.57252(19) 0.85783(13) 0.21209(10) 0.0241(3) Uani d . 1 . . C
C31 0.4471(2) 1.02782(16) 0.14173(14) 0.0391(4) Uani d . 1 . . C
H31A 0.4913 1.1026 0.1472 0.059 Uiso calc R 1 . . H
H31B 0.3785 1.0180 0.1830 0.059 Uiso calc R 1 . . H
H31C 0.3841 1.0153 0.0849 0.059 Uiso calc R 1 . . H
O32 0.70962(18) 1.05396(11) 0.07859(9) 0.0399(3) Uani d . 1 . . O
C33 0.9797(2) 0.93739(16) 0.10263(13) 0.0365(4) Uani d . 1 . . C
H33A 1.0570 0.9749 0.1473 0.055 Uiso calc R 1 . . H
H33B 0.9467 0.9873 0.0562 0.055 Uiso calc R 1 . . H
H33C 1.0291 0.8727 0.0821 0.055 Uiso calc R 1 . . H
O34 0.97229(16) 0.75531(11) 0.19305(9) 0.0352(3) Uani d . 1 . . O
C36 0.4054(2) 0.80402(14) 0.19543(11) 0.0278(3) Uani d . 1 . . C
H36A 0.4073 0.7397 0.2315 0.033 Uiso calc R 1 . . H
H36B 0.3284 0.8567 0.2115 0.033 Uiso calc R 1 . . H
C37 0.3476(2) 0.76733(16) 0.10347(12) 0.0339(4) Uani d . 1 . . C
H37A 0.2408 0.7340 0.0966 0.051 Uiso calc R 1 . . H
H37B 0.4218 0.7136 0.0875 0.051 Uiso calc R 1 . . H
H37C 0.3433 0.8309 0.0675 0.051 Uiso calc R 1 . . H
N41 1.06470(17) 0.33577(11) 0.12378(9) 0.0258(3) Uani d . 1 . . N
C42 1.1967(2) 0.30735(14) 0.09367(10) 0.0272(3) Uani d . 1 . . C
N43 1.33438(17) 0.37560(11) 0.11495(9) 0.0266(3) Uani d . 1 . . N
C44 1.3473(2) 0.46994(13) 0.16361(10) 0.0249(3) Uani d . 1 . . C
C45 1.19840(19) 0.50924(12) 0.19143(10) 0.0231(3) Uani d . 1 . . C
H45 1.1610 0.5801 0.1654 0.028 Uiso calc R 1 . . H
C46 1.06037(18) 0.42492(12) 0.18442(10) 0.0220(3) Uani d . 1 . . C
C51 0.9266(2) 0.26086(16) 0.10311(13) 0.0377(4) Uani d . 1 . . C
H51A 0.8466 0.2914 0.0582 0.057 Uiso calc R 1 . . H
H51B 0.8799 0.2513 0.1531 0.057 Uiso calc R 1 . . H
H51C 0.9611 0.1898 0.0842 0.057 Uiso calc R 1 . . H
O52 1.20133(18) 0.22605(12) 0.04861(9) 0.0414(3) Uani d . 1 . . O
C53 1.4775(2) 0.33980(17) 0.08491(14) 0.0399(4) Uani d . 1 . . C
H53A 1.5232 0.4014 0.0596 0.060 Uiso calc R 1 . . H
H53B 1.4486 0.2803 0.0428 0.060 Uiso calc R 1 . . H
H53C 1.5565 0.3137 0.1323 0.060 Uiso calc R 1 . . H
O54 1.47316(16) 0.52123(11) 0.18192(9) 0.0365(3) Uani d . 1 . . O
C56 0.8985(2) 0.48275(14) 0.16759(10) 0.0268(3) Uani d . 1 . . C
H56A 0.8144 0.4306 0.1765 0.032 Uiso calc R 1 . . H
H56B 0.9021 0.5443 0.2089 0.032 Uiso calc R 1 . . H
C57 0.8531(2) 0.52681(17) 0.07899(12) 0.0362(4) Uani d . 1 . . C
H57A 0.7491 0.5625 0.0724 0.054 Uiso calc R 1 . . H
H57B 0.8466 0.4662 0.0376 0.054 Uiso calc R 1 . . H
H57C 0.9344 0.5800 0.0700 0.054 Uiso calc R 1 . . H
N61 1.24209(17) 0.31417(11) 0.29264(9) 0.0270(3) Uani d . 1 . . N
C62 1.3964(2) 0.32677(16) 0.33367(12) 0.0330(4) Uani d . 1 . . C
N63 1.45316(18) 0.43230(14) 0.36280(10) 0.0333(3) Uani d . 1 . . N
C64 1.3696(2) 0.52663(15) 0.34441(10) 0.0284(3) Uani d . 1 . . C
C65 1.20846(18) 0.51303(12) 0.28874(10) 0.0222(3) Uani d . 1 . . C
H65 1.1359 0.5709 0.3037 0.027 Uiso calc R 1 . . H
C66 1.12193(18) 0.40039(12) 0.28203(10) 0.0224(3) Uani d . 1 . . C
C71 1.1882(3) 0.19960(15) 0.27811(14) 0.0393(4) Uani d . 1 . . C
H71A 1.2370 0.1661 0.2338 0.059 Uiso calc R 1 . . H
H71B 1.0715 0.1967 0.2606 0.059 Uiso calc R 1 . . H
H71C 1.2201 0.1595 0.3302 0.059 Uiso calc R 1 . . H
O72 1.4870(2) 0.24925(14) 0.34606(12) 0.0526(4) Uani d . 1 . . O
C73 1.6170(2) 0.4408(2) 0.41237(15) 0.0507(6) Uani d . 1 . . C
H73A 1.6585 0.5154 0.4098 0.076 Uiso calc R 1 . . H
H73B 1.6853 0.3889 0.3893 0.076 Uiso calc R 1 . . H
H73C 1.6164 0.4236 0.4710 0.076 Uiso calc R 1 . . H
O74 1.42366(17) 0.61632(12) 0.37140(9) 0.0384(3) Uani d . 1 . . O
C76 0.9985(2) 0.38518(14) 0.33795(11) 0.0284(3) Uani d . 1 . . C
H76A 0.9201 0.4450 0.3282 0.034 Uiso calc R 1 . . H
H76B 0.9400 0.3150 0.3222 0.034 Uiso calc R 1 . . H
C77 1.0757(3) 0.3852(2) 0.43045(13) 0.0502(6) Uani d . 1 . . C
H77A 0.9930 0.3758 0.4641 0.075 Uiso calc R 1 . . H
H77B 1.1327 0.4549 0.4465 0.075 Uiso calc R 1 . . H
H77C 1.1514 0.3248 0.4406 0.075 Uiso calc R 1 . . H
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
_geom_angle_publ_flag
C2 N1 C6 125.26(14) n
C2 N1 C11 114.40(15) n
C6 N1 C11 118.08(15) n
O12 C2 N1 121.95(18) n
O12 C2 N3 119.52(18) n
N1 C2 N3 118.53(15) n
C4 N3 C2 124.40(15) n
C4 N3 C13 117.78(15) n
C2 N3 C13 117.65(16) n
O14 C4 N3 121.92(16) n
O14 C4 C5 122.10(16) n
N3 C4 C5 115.98(14) n
C4 C5 C6 119.52(14) n
C4 C5 C25 118.08(13) n
C6 C5 C25 89.75(11) n
C4 C5 H5 109.3 n
C6 C5 H5 109.3 n
C25 C5 H5 109.3 n
N1 C6 C16 112.34(14) n
N1 C6 C5 108.30(13) n
C16 C6 C5 116.52(13) n
N1 C6 C26 110.80(13) n
C16 C6 C26 119.49(14) n
C5 C6 C26 86.61(11) n
N1 C11 H11A 109.5 n
N1 C11 H11B 109.5 n
H11A C11 H11B 109.5 n
N1 C11 H11C 109.5 n
H11A C11 H11C 109.5 n
H11B C11 H11C 109.5 n
N3 C13 H13A 109.5 n
N3 C13 H13B 109.5 n
H13A C13 H13B 109.5 n
N3 C13 H13C 109.5 n
H13A C13 H13C 109.5 n
H13B C13 H13C 109.5 n
C17 C16 C6 112.79(15) n
C17 C16 H16A 109.0 n
C6 C16 H16A 109.0 n
C17 C16 H16B 109.0 n
C6 C16 H16B 109.0 n
H16A C16 H16B 107.8 n
C16 C17 H17A 109.5 n
C16 C17 H17B 109.5 n
H17A C17 H17B 109.5 n
C16 C17 H17C 109.5 n
H17A C17 H17C 109.5 n
H17B C17 H17C 109.5 n
C22 N21 C26 124.03(14) n
C22 N21 C31 115.42(14) n
C26 N21 C31 120.38(14) n
O32 C22 N21 122.24(17) n
O32 C22 N23 119.11(16) n
N21 C22 N23 118.64(14) n
C24 N23 C22 125.51(14) n
C24 N23 C33 117.58(15) n
C22 N23 C33 116.90(14) n
O34 C24 N23 121.61(15) n
O34 C24 C25 121.32(15) n
N23 C24 C25 117.06(14) n
C24 C25 C26 116.29(13) n
C24 C25 C5 114.27(13) n
C26 C25 C5 88.20(11) n
C24 C25 H25 112.0 n
C26 C25 H25 112.0 n
C5 C25 H25 112.0 n
N21 C26 C36 111.11(13) n
N21 C26 C25 114.15(13) n
C36 C26 C25 110.07(13) n
N21 C26 C6 118.64(13) n
C36 C26 C6 112.60(13) n
C25 C26 C6 88.27(11) n
N21 C31 H31A 109.5 n
N21 C31 H31B 109.5 n
H31A C31 H31B 109.5 n
N21 C31 H31C 109.5 n
H31A C31 H31C 109.5 n
H31B C31 H31C 109.5 n
N23 C33 H33A 109.5 n
N23 C33 H33B 109.5 n
H33A C33 H33B 109.5 n
N23 C33 H33C 109.5 n
H33A C33 H33C 109.5 n
H33B C33 H33C 109.5 n
C37 C36 C26 113.08(14) n
C37 C36 H36A 109.0 n
C26 C36 H36A 109.0 n
C37 C36 H36B 109.0 n
C26 C36 H36B 109.0 n
H36A C36 H36B 107.8 n
C36 C37 H37A 109.5 n
C36 C37 H37B 109.5 n
H37A C37 H37B 109.5 n
C36 C37 H37C 109.5 n
H37A C37 H37C 109.5 n
H37B C37 H37C 109.5 n
C42 N41 C46 124.19(14) n
C42 N41 C51 116.67(14) n
C46 N41 C51 118.46(14) n
O52 C42 N41 122.91(16) n
O52 C42 N43 118.81(16) n
N41 C42 N43 118.28(14) n
C44 N43 C42 125.75(14) n
C44 N43 C53 117.25(15) n
C42 N43 C53 116.95(14) n
O54 C44 N43 121.32(15) n
O54 C44 C45 121.43(15) n
N43 C44 C45 117.23(14) n
C44 C45 C46 116.34(13) n
C44 C45 C65 114.83(13) n
C46 C45 C65 88.10(11) n
C44 C45 H45 111.9 n
C46 C45 H45 111.9 n
C65 C45 H45 111.9 n
N41 C46 C56 111.52(13) n
N41 C46 C45 114.34(13) n
C56 C46 C45 110.35(13) n
N41 C46 C66 117.54(13) n
C56 C46 C66 112.72(12) n
C45 C46 C66 88.36(11) n
N41 C51 H51A 109.5 n
N41 C51 H51B 109.5 n
H51A C51 H51B 109.5 n
N41 C51 H51C 109.5 n
H51A C51 H51C 109.5 n
H51B C51 H51C 109.5 n
N43 C53 H53A 109.5 n
N43 C53 H53B 109.5 n
H53A C53 H53B 109.5 n
N43 C53 H53C 109.5 n
H53A C53 H53C 109.5 n
H53B C53 H53C 109.5 n
C57 C56 C46 113.59(14) n
C57 C56 H56A 108.8 n
C46 C56 H56A 108.8 n
C57 C56 H56B 108.8 n
C46 C56 H56B 108.8 n
H56A C56 H56B 107.7 n
C56 C57 H57A 109.5 n
C56 C57 H57B 109.5 n
H57A C57 H57B 109.5 n
C56 C57 H57C 109.5 n
H57A C57 H57C 109.5 n
H57B C57 H57C 109.5 n
C62 N61 C66 125.32(14) n
C62 N61 C71 114.09(15) n
C66 N61 C71 118.72(15) n
O72 C62 N61 121.88(19) n
O72 C62 N63 119.25(19) n
N61 C62 N63 118.86(15) n
C64 N63 C62 124.51(15) n
C64 N63 C73 118.47(18) n
C62 N63 C73 116.93(17) n
O74 C64 N63 122.13(17) n
O74 C64 C65 122.09(16) n
N63 C64 C65 115.78(15) n
C64 C65 C66 119.28(14) n
C64 C65 C45 118.15(13) n
C66 C65 C45 89.72(11) n
C64 C65 H65 109.4 n
C66 C65 H65 109.4 n
C45 C65 H65 109.4 n
N61 C66 C76 112.42(13) n
N61 C66 C65 108.79(13) n
C76 C66 C65 116.59(13) n
N61 C66 C46 111.02(12) n
C76 C66 C46 118.80(13) n
C65 C66 C46 86.48(11) n
N61 C71 H71A 109.5 n
N61 C71 H71B 109.5 n
H71A C71 H71B 109.5 n
N61 C71 H71C 109.5 n
H71A C71 H71C 109.5 n
H71B C71 H71C 109.5 n
N63 C73 H73A 109.5 n
N63 C73 H73B 109.5 n
H73A C73 H73B 109.5 n
N63 C73 H73C 109.5 n
H73A C73 H73C 109.5 n
H73B C73 H73C 109.5 n
C77 C76 C66 111.94(15) n
C77 C76 H76A 109.2 n
C66 C76 H76A 109.2 n
C77 C76 H76B 109.2 n
C66 C76 H76B 109.2 n
H76A C76 H76B 107.9 n
C76 C77 H77A 109.5 n
C76 C77 H77B 109.5 n
H77A C77 H77B 109.5 n
C76 C77 H77C 109.5 n
H77A C77 H77C 109.5 n
H77B C77 H77C 109.5 n
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
N1 C2 . 1.360(2) n
N1 C6 . 1.466(2) n
N1 C11 . 1.469(2) n
C2 O12 . 1.219(2) n
C2 N3 . 1.413(2) n
N3 C4 . 1.371(2) n
N3 C13 . 1.471(2) n
C4 O14 . 1.223(2) n
C4 C5 . 1.496(2) n
C5 C6 . 1.547(2) n
C5 C25 . 1.560(2) n
C5 H5 . 1.0000 n
C6 C16 . 1.527(2) n
C6 C26 . 1.603(2) n
C11 H11A . 0.9800 n
C11 H11B . 0.9800 n
C11 H11C . 0.9800 n
C13 H13A . 0.9800 n
C13 H13B . 0.9800 n
C13 H13C . 0.9800 n
C16 C17 . 1.525(3) n
C16 H16A . 0.9900 n
C16 H16B . 0.9900 n
C17 H17A . 0.9800 n
C17 H17B . 0.9800 n
C17 H17C . 0.9800 n
N21 C22 . 1.356(2) n
N21 C26 . 1.455(2) n
N21 C31 . 1.470(2) n
C22 O32 . 1.225(2) n
C22 N23 . 1.416(2) n
N23 C24 . 1.368(2) n
N23 C33 . 1.467(2) n
C24 O34 . 1.226(2) n
C24 C25 . 1.505(2) n
C25 C26 . 1.544(2) n
C25 H25 . 1.0000 n
C26 C36 . 1.536(2) n
C31 H31A . 0.9800 n
C31 H31B . 0.9800 n
C31 H31C . 0.9800 n
C33 H33A . 0.9800 n
C33 H33B . 0.9800 n
C33 H33C . 0.9800 n
C36 C37 . 1.530(2) n
C36 H36A . 0.9900 n
C36 H36B . 0.9900 n
C37 H37A . 0.9800 n
C37 H37B . 0.9800 n
C37 H37C . 0.9800 n
N41 C42 . 1.356(2) n
N41 C46 . 1.454(2) n
N41 C51 . 1.465(2) n
C42 O52 . 1.223(2) n
C42 N43 . 1.415(2) n
N43 C44 . 1.371(2) n
N43 C53 . 1.466(2) n
C44 O54 . 1.220(2) n
C44 C45 . 1.506(2) n
C45 C46 . 1.543(2) n
C45 C65 . 1.562(2) n
C45 H45 . 1.0000 n
C46 C56 . 1.536(2) n
C46 C66 . 1.604(2) n
C51 H51A . 0.9800 n
C51 H51B . 0.9800 n
C51 H51C . 0.9800 n
C53 H53A . 0.9800 n
C53 H53B . 0.9800 n
C53 H53C . 0.9800 n
C56 C57 . 1.526(2) n
C56 H56A . 0.9900 n
C56 H56B . 0.9900 n
C57 H57A . 0.9800 n
C57 H57B . 0.9800 n
C57 H57C . 0.9800 n
N61 C62 . 1.359(2) n
N61 C66 . 1.4662(19) n
N61 C71 . 1.468(2) n
C62 O72 . 1.223(2) n
C62 N63 . 1.410(3) n
N63 C64 . 1.369(2) n
N63 C73 . 1.471(2) n
C64 O74 . 1.222(2) n
C64 C65 . 1.495(2) n
C65 C66 . 1.547(2) n
C65 H65 . 1.0000 n
C66 C76 . 1.530(2) n
C71 H71A . 0.9800 n
C71 H71B . 0.9800 n
C71 H71C . 0.9800 n
C73 H73A . 0.9800 n
C73 H73B . 0.9800 n
C73 H73C . 0.9800 n
C76 C77 . 1.515(3) n
C76 H76A . 0.9900 n
C76 H76B . 0.9900 n
C77 H77A . 0.9800 n
C77 H77B . 0.9800 n
C77 H77C . 0.9800 n
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
_geom_torsion_publ_flag
C6 N1 C2 O12 -169.77(18) n
C11 N1 C2 O12 -7.3(3) n
C6 N1 C2 N3 11.0(3) n
C11 N1 C2 N3 173.42(17) n
O12 C2 N3 C4 -172.19(18) n
N1 C2 N3 C4 7.1(3) n
O12 C2 N3 C13 2.9(3) n
N1 C2 N3 C13 -177.80(17) n
C2 N3 C4 O14 177.70(16) n
C13 N3 C4 O14 2.6(2) n
C2 N3 C4 C5 -2.4(2) n
C13 N3 C4 C5 -177.47(16) n
O14 C4 C5 C6 161.39(15) n
N3 C4 C5 C6 -18.5(2) n
O14 C4 C5 C25 -91.37(19) n
N3 C4 C5 C25 88.71(17) n
C2 N1 C6 C16 101.55(19) n
C11 N1 C6 C16 -60.3(2) n
C2 N1 C6 C5 -28.6(2) n
C11 N1 C6 C5 169.55(15) n
C2 N1 C6 C26 -121.95(17) n
C11 N1 C6 C26 76.17(19) n
C4 C5 C6 N1 31.59(19) n
C25 C5 C6 N1 -90.98(14) n
C4 C5 C6 C16 -96.18(18) n
C25 C5 C6 C16 141.25(15) n
C4 C5 C6 C26 142.39(14) n
C25 C5 C6 C26 19.82(11) n
N1 C6 C16 C17 -62.4(2) n
C5 C6 C16 C17 63.3(2) n
C26 C6 C16 C17 165.24(16) n
C26 N21 C22 O32 -176.47(17) n
C31 N21 C22 O32 -1.2(3) n
C26 N21 C22 N23 2.6(2) n
C31 N21 C22 N23 177.81(16) n
O32 C22 N23 C24 -177.07(17) n
N21 C22 N23 C24 3.9(3) n
O32 C22 N23 C33 4.2(2) n
N21 C22 N23 C33 -174.88(16) n
C22 N23 C24 O34 -176.01(16) n
C33 N23 C24 O34 2.7(2) n
C22 N23 C24 C25 5.4(2) n
C33 N23 C24 C25 -175.89(15) n
O34 C24 C25 C26 161.92(16) n
N23 C24 C25 C26 -19.5(2) n
O34 C24 C25 C5 61.3(2) n
N23 C24 C25 C5 -120.07(15) n
C4 C5 C25 C24 -26.20(19) n
C6 C5 C25 C24 97.58(14) n
C4 C5 C25 C26 -144.36(14) n
C6 C5 C25 C26 -20.58(12) n
C22 N21 C26 C36 -141.73(16) n
C31 N21 C26 C36 43.2(2) n
C22 N21 C26 C25 -16.5(2) n
C31 N21 C26 C25 168.42(16) n
C22 N21 C26 C6 85.4(2) n
C31 N21 C26 C6 -89.62(19) n
C24 C25 C26 N21 24.3(2) n
C5 C25 C26 N21 140.63(14) n
C24 C25 C26 C36 150.04(14) n
C5 C25 C26 C36 -93.65(14) n
C24 C25 C26 C6 -96.48(14) n
C5 C25 C26 C6 19.83(11) n
N1 C6 C26 N21 -28.48(19) n
C16 C6 C26 N21 104.52(17) n
C5 C6 C26 N21 -136.77(14) n
N1 C6 C26 C36 -160.69(13) n
C16 C6 C26 C36 -27.69(19) n
C5 C6 C26 C36 91.02(14) n
N1 C6 C26 C25 88.25(13) n
C16 C6 C26 C25 -138.75(15) n
C5 C6 C26 C25 -20.04(11) n
N21 C26 C36 C37 55.30(18) n
C25 C26 C36 C37 -72.13(17) n
C6 C26 C36 C37 -168.87(14) n
C46 N41 C42 O52 173.20(16) n
C51 N41 C42 O52 2.9(3) n
C46 N41 C42 N43 -7.4(2) n
C51 N41 C42 N43 -177.70(15) n
O52 C42 N43 C44 179.03(17) n
N41 C42 N43 C44 -0.4(2) n
O52 C42 N43 C53 -3.5(2) n
N41 C42 N43 C53 177.06(16) n
C42 N43 C44 O54 176.67(16) n
C53 N43 C44 O54 -0.8(2) n
C42 N43 C44 C45 -5.0(2) n
C53 N43 C44 C45 177.51(15) n
O54 C44 C45 C46 -164.98(15) n
N43 C44 C45 C46 16.7(2) n
O54 C44 C45 C65 -64.1(2) n
N43 C44 C45 C65 117.55(16) n
C42 N41 C46 C56 145.02(16) n
C51 N41 C46 C56 -44.8(2) n
C42 N41 C46 C45 18.9(2) n
C51 N41 C46 C45 -170.88(15) n
C42 N41 C46 C66 -82.62(19) n
C51 N41 C46 C66 87.56(19) n
C44 C45 C46 N41 -22.8(2) n
C65 C45 C46 N41 -139.70(13) n
C44 C45 C46 C56 -149.47(14) n
C65 C45 C46 C56 93.62(13) n
C44 C45 C46 C66 96.85(14) n
C65 C45 C46 C66 -20.05(11) n
N41 C46 C56 C57 -56.56(19) n
C45 C46 C56 C57 71.67(18) n
C66 C46 C56 C57 168.69(14) n
C66 N61 C62 O72 174.02(17) n
C71 N61 C62 O72 9.9(3) n
C66 N61 C62 N63 -5.9(3) n
C71 N61 C62 N63 -170.01(16) n
O72 C62 N63 C64 172.08(18) n
N61 C62 N63 C64 -8.0(3) n
O72 C62 N63 C73 -4.4(3) n
N61 C62 N63 C73 175.50(17) n
C62 N63 C64 O74 179.75(17) n
C73 N63 C64 O74 -3.8(3) n
C62 N63 C64 C65 -0.6(2) n
C73 N63 C64 C65 175.78(16) n
O74 C64 C65 C66 -158.63(15) n
N63 C64 C65 C66 21.8(2) n
O74 C64 C65 C45 94.29(19) n
N63 C64 C65 C45 -85.32(18) n
C44 C45 C65 C64 26.0(2) n
C46 C45 C65 C64 144.32(14) n
C44 C45 C65 C66 -97.47(14) n
C46 C45 C65 C66 20.81(11) n
C62 N61 C66 C76 -106.50(18) n
C71 N61 C66 C76 57.0(2) n
C62 N61 C66 C65 24.2(2) n
C71 N61 C66 C65 -172.35(14) n
C62 N61 C66 C46 117.70(17) n
C71 N61 C66 C46 -78.84(18) n
C64 C65 C66 N61 -31.56(19) n
C45 C65 C66 N61 91.01(13) n
C64 C65 C66 C76 96.82(17) n
C45 C65 C66 C76 -140.61(14) n
C64 C65 C66 C46 -142.58(14) n
C45 C65 C66 C46 -20.01(11) n
N41 C46 C66 N61 28.26(18) n
C56 C46 C66 N61 160.08(13) n
C45 C46 C66 N61 -88.50(13) n
N41 C46 C66 C76 -104.40(16) n
C56 C46 C66 C76 27.42(19) n
C45 C46 C66 C76 138.84(14) n
N41 C46 C66 C65 137.04(13) n
C56 C46 C66 C65 -91.13(13) n
C45 C46 C66 C65 20.29(11) n
N61 C66 C76 C77 59.3(2) n
C65 C66 C76 C77 -67.3(2) n
C46 C66 C76 C77 -168.70(16) n
