#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/10/2201023.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_2201023
loop_
_publ_author_name
'Näther, Christian'
'Krüger, Oliver'
'Wille, Uta'
_publ_section_title
cis-[4a]-cisoid-[4a,4b]-cis-[4b]-1,3,6,8,8a,8b-Hexamethylperhydro-1,3,6,8-tetraazabiphenylene-2,4,5,7-tetraone
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o409
_journal_page_last               o410
_journal_paper_doi               10.1107/S1600536802004476
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C14 H20 N4 O4'
_chemical_formula_moiety         'C14 H20 N4 O4'
_chemical_formula_sum            'C14 H20 N4 O4'
_chemical_formula_weight         308.34
_chemical_name_common
;
cis-[4a]-cisoid-[4a,4b]-cis-[4b]-1,3,6,8,8a,8b-Hexamethylperhydro-
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                81.743(10)
_cell_angle_beta                 75.761(10)
_cell_angle_gamma                84.015(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0365(6)
_cell_length_b                   8.0400(6)
_cell_length_c                   13.0172(10)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      10
_cell_volume                     704.58(10)
_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 0.966
_diffrn_measured_fraction_theta_max 0.966
_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  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0349
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6641
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular block'
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.263
_refine_ls_extinction_coef       0.094(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0430
_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)+(0.0754P)²+0.1990P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1237
_reflns_number_gt                2973
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6121.cif
_cod_data_source_block           I
_cod_database_code               2201023
_cod_database_fobs_code          2201023
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 0.63714(14) 0.84771(11) 0.66870(8) 0.0159(2) Uani d . 1 . . N
C2 0.68899(17) 0.73523(14) 0.59671(9) 0.0174(2) Uani d . 1 . . C
N3 0.70675(14) 0.56167(11) 0.63527(8) 0.0171(2) Uani d . 1 . . N
C4 0.65798(16) 0.49583(13) 0.73982(9) 0.0158(2) Uani d . 1 . . C
C5 0.58686(15) 0.61641(13) 0.82143(9) 0.0146(2) Uani d . 1 . . C
H5 0.4497 0.5969 0.8632 0.018 Uiso calc R 1 . . H
C6 0.61209(15) 0.80445(13) 0.78251(9) 0.0143(2) Uani d . 1 . . C
C11 0.6206(2) 1.02548(14) 0.62491(10) 0.0227(3) Uani d . 1 . . C
H11A 0.7173 1.0443 0.5567 0.034 Uiso calc R 1 . . H
H11B 0.6454 1.0958 0.6752 0.034 Uiso calc R 1 . . H
H11C 0.4880 1.0553 0.6136 0.034 Uiso calc R 1 . . H
O12 0.72258(16) 0.77829(12) 0.50078(7) 0.0299(2) Uani d . 1 . . O
C13 0.7498(2) 0.44230(16) 0.55585(11) 0.0287(3) Uani d . 1 . . C
H13A 0.8541 0.3583 0.5706 0.043 Uiso calc R 1 . . H
H13B 0.7929 0.5032 0.4843 0.043 Uiso calc R 1 . . H
H13C 0.6310 0.3857 0.5596 0.043 Uiso calc R 1 . . H
O14 0.66773(13) 0.34391(10) 0.76755(7) 0.0228(2) Uani d . 1 . . O
C16 0.44267(18) 0.91138(15) 0.84448(10) 0.0222(3) Uani d . 1 . . C
H16A 0.4779 1.0283 0.8351 0.033 Uiso calc R 1 . . H
H16B 0.4162 0.8675 0.9205 0.033 Uiso calc R 1 . . H
H16C 0.3249 0.9072 0.8177 0.033 Uiso calc R 1 . . H
N21 0.98113(14) 0.75203(12) 0.74908(8) 0.0171(2) Uani d . 1 . . N
C22 1.09903(16) 0.60751(14) 0.75019(9) 0.0168(2) Uani d . 1 . . C
N23 1.03698(14) 0.47048(12) 0.82747(8) 0.0176(2) Uani d . 1 . . N
C24 0.87035(17) 0.47558(14) 0.90824(9) 0.0168(2) Uani d . 1 . . C
C25 0.72774(16) 0.62365(13) 0.89631(9) 0.0150(2) Uani d . 1 . . C
H25 0.6488 0.6478 0.9684 0.018 Uiso calc R 1 . . H
C26 0.80319(16) 0.78923(13) 0.82991(9) 0.0149(2) Uani d . 1 . . C
C31 1.06030(18) 0.88794(16) 0.66690(10) 0.0255(3) Uani d . 1 . . C
H31A 1.1977 0.8986 0.6670 0.038 Uiso calc R 1 . . H
H31B 0.9833 0.9942 0.6820 0.038 Uiso calc R 1 . . H
H31C 1.0528 0.8620 0.5968 0.038 Uiso calc R 1 . . H
O32 1.25668(13) 0.59161(12) 0.68624(8) 0.0267(2) Uani d . 1 . . O
C33 1.16670(19) 0.31616(16) 0.82218(12) 0.0270(3) Uani d . 1 . . C
H33A 1.2859 0.3333 0.8443 0.041 Uiso calc R 1 . . H
H33B 1.2024 0.2878 0.7488 0.041 Uiso calc R 1 . . H
H33C 1.0988 0.2239 0.8699 0.041 Uiso calc R 1 . . H
O34 0.83755(14) 0.36393(11) 0.98304(8) 0.0266(2) Uani d . 1 . . O
C36 0.8311(2) 0.92607(15) 0.89305(10) 0.0239(3) Uani d . 1 . . C
H36A 0.9488 0.8954 0.9212 0.036 Uiso calc R 1 . . H
H36B 0.7160 0.9379 0.9525 0.036 Uiso calc R 1 . . H
H36C 0.8467 1.0332 0.8463 0.036 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 124.47(9) n
C2 N1 C11 116.27(10) n
C6 N1 C11 119.10(9) n
O12 C2 N1 122.37(10) n
O12 C2 N3 119.29(11) n
N1 C2 N3 118.34(10) n
C4 N3 C2 125.16(10) n
C4 N3 C13 116.99(10) n
C2 N3 C13 117.05(10) n
O14 C4 N3 121.96(11) n
O14 C4 C5 120.34(11) n
N3 C4 C5 117.70(9) n
C4 C5 C6 116.96(9) n
C4 C5 C25 114.62(9) n
C6 C5 C25 88.71(8) n
C4 C5 H5 111.6 n
C6 C5 H5 111.6 n
C25 C5 H5 111.6 n
N1 C6 C16 111.52(9) n
N1 C6 C5 114.15(9) n
C16 C6 C5 110.05(9) n
N1 C6 C26 117.89(9) n
C16 C6 C26 112.36(9) n
C5 C6 C26 88.91(8) 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
C6 C16 H16A 109.5 n
C6 C16 H16B 109.5 n
H16A C16 H16B 109.5 n
C6 C16 H16C 109.5 n
H16A C16 H16C 109.5 n
H16B C16 H16C 109.5 n
C22 N21 C26 125.84(10) n
C22 N21 C31 114.74(10) n
C26 N21 C31 118.77(9) n
O32 C22 N21 122.33(11) n
O32 C22 N23 118.74(11) n
N21 C22 N23 118.93(10) n
C24 N23 C22 124.54(9) n
C24 N23 C33 118.97(10) n
C22 N23 C33 116.43(10) n
O34 C24 N23 122.40(11) n
O34 C24 C25 122.15(10) n
N23 C24 C25 115.40(9) n
C24 C25 C26 119.30(9) n
C24 C25 C5 117.43(9) n
C26 C25 C5 89.95(8) n
C24 C25 H25 109.6 n
C26 C25 H25 109.6 n
C5 C25 H25 109.6 n
N21 C26 C36 111.42(9) n
N21 C26 C25 109.83(8) n
C36 C26 C25 116.07(9) n
N21 C26 C6 111.30(9) n
C36 C26 C6 118.88(9) n
C25 C26 C6 87.09(8) 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
C26 C36 H36A 109.5 n
C26 C36 H36B 109.5 n
H36A C36 H36B 109.5 n
C26 C36 H36C 109.5 n
H36A C36 H36C 109.5 n
H36B C36 H36C 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 . 1.3547(14) n
N1 C6 . 1.4434(14) n
N1 C11 . 1.4647(14) n
C2 O12 . 1.2177(15) n
C2 N3 . 1.4171(14) n
N3 C4 . 1.3607(15) n
N3 C13 . 1.4669(15) n
C4 O14 . 1.2227(13) n
C4 C5 . 1.5007(15) n
C5 C6 . 1.5381(14) n
C5 C25 . 1.5620(16) n
C5 H5 . 1.0000 n
C6 C16 . 1.5243(15) n
C6 C26 . 1.5987(15) 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 H16A . 0.9800 n
C16 H16B . 0.9800 n
C16 H16C . 0.9800 n
N21 C22 . 1.3559(15) n
N21 C26 . 1.4589(14) n
N21 C31 . 1.4652(14) n
C22 O32 . 1.2192(14) n
C22 N23 . 1.4080(15) n
N23 C24 . 1.3703(15) n
N23 C33 . 1.4611(15) n
C24 O34 . 1.2201(14) n
C24 C25 . 1.4909(15) n
C25 C26 . 1.5467(14) n
C25 H25 . 1.0000 n
C26 C36 . 1.5195(15) 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 H36A . 0.9800 n
C36 H36B . 0.9800 n
C36 H36C . 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 -174.50(11) n
C11 N1 C2 O12 0.86(17) n
C6 N1 C2 N3 4.69(16) n
C11 N1 C2 N3 -179.96(10) n
O12 C2 N3 C4 -174.23(11) n
N1 C2 N3 C4 6.56(17) n
O12 C2 N3 C13 -4.87(17) n
N1 C2 N3 C13 175.92(10) n
C2 N3 C4 O14 176.34(10) n
C13 N3 C4 O14 6.97(16) n
C2 N3 C4 C5 -2.45(16) n
C13 N3 C4 C5 -171.81(10) n
O14 C4 C5 C6 169.85(10) n
N3 C4 C5 C6 -11.35(14) n
O14 C4 C5 C25 67.99(13) n
N3 C4 C5 C25 -113.20(11) n
C2 N1 C6 C16 -143.17(11) n
C11 N1 C6 C16 41.59(13) n
C2 N1 C6 C5 -17.68(15) n
C11 N1 C6 C5 167.09(9) n
C2 N1 C6 C26 84.66(13) n
C11 N1 C6 C26 -90.57(12) n
C4 C5 C6 N1 20.32(13) n
C25 C5 C6 N1 137.46(9) n
C4 C5 C6 C16 146.59(10) n
C25 C5 C6 C16 -96.27(10) n
C4 C5 C6 C26 -99.96(10) n
C25 C5 C6 C26 17.18(8) n
C26 N21 C22 O32 -171.92(11) n
C31 N21 C22 O32 -1.37(16) n
C26 N21 C22 N23 8.44(17) n
C31 N21 C22 N23 179.00(10) n
O32 C22 N23 C24 175.21(10) n
N21 C22 N23 C24 -5.14(17) n
O32 C22 N23 C33 -1.87(16) n
N21 C22 N23 C33 177.78(10) n
C22 N23 C24 O34 -168.14(11) n
C33 N23 C24 O34 8.87(17) n
C22 N23 C24 C25 14.21(16) n
C33 N23 C24 C25 -168.78(10) n
O34 C24 C25 C26 156.27(11) n
N23 C24 C25 C26 -26.08(14) n
O34 C24 C25 C5 -96.86(13) n
N23 C24 C25 C5 80.79(12) n
C4 C5 C25 C24 -21.96(13) n
C6 C5 C25 C24 -141.21(10) n
C4 C5 C25 C26 101.47(10) n
C6 C5 C25 C26 -17.78(8) n
C22 N21 C26 C36 111.03(12) n
C31 N21 C26 C36 -59.18(13) n
C22 N21 C26 C25 -19.01(15) n
C31 N21 C26 C25 170.78(10) n
C22 N21 C26 C6 -113.75(12) n
C31 N21 C26 C6 76.04(12) n
C24 C25 C26 N21 27.35(13) n
C5 C25 C26 N21 -94.51(9) n
C24 C25 C26 C36 -100.14(12) n
C5 C25 C26 C36 138.00(10) n
C24 C25 C26 C6 138.96(10) n
C5 C25 C26 C6 17.10(8) n
N1 C6 C26 N21 -24.14(12) n
C16 C6 C26 N21 -155.93(9) n
C5 C6 C26 N21 92.79(9) n
N1 C6 C26 C36 107.37(12) n
C16 C6 C26 C36 -24.42(14) n
C5 C6 C26 C36 -135.70(10) n
N1 C6 C26 C25 -134.31(9) n
C16 C6 C26 C25 93.90(9) n
C5 C6 C26 C25 -17.37(8) n
