##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-08-31
_journal_date_accepted     2005-09-05
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue     10
_journal_page_first     o3164
_journal_page_last     o3165
_journal_paper_category     EO
_journal_coeditor_code     JH6016
_publ_contact_author_name     'Qin, Shuqi'
_publ_contact_author_address
; College of Chemistry and Engineering
   Northwest Normal University
   Lanzhou  730070
   China
;
_publ_contact_author_email     qinsq@nwnu.edu.cn
_publ_contact_author_fax     '86 931 3435519'
_publ_contact_author_phone     ' '
_publ_section_title
;\
Diethyl
(11bR,11cS)-rel-5,10-dihydro-7-nitro-4,11-dioxo-\
1H,3H,4H,11H-2-oxa-
3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,\
11c-dicarboxylate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Qin, Shuqi' .
;
College of Chemistry and Engineering
Northwest Normal University
Lanzhou  30070
People's Republic of China
;
    'Yin, Guodong' .
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Diethyl
(11bR,11cS)-rel-5,10-dihydro-7-nitro-4,11-dioxo-1H,3H,4H,11H-2-oxa-
3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H21 N5 O9'
_chemical_formula_sum     'C20 H21 N5 O9'
_chemical_formula_iupac     'C20 H21 N5 O9'
_chemical_formula_weight     475.42
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     -P2ybc
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.0454(18)
_cell_length_b     25.564(5)
_cell_length_c     8.4997(15)
_cell_angle_alpha     90.00
_cell_angle_beta     99.427(3)
_cell_angle_gamma     90.00
_cell_volume     2153.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3635
_cell_measurement_theta_min     2.20
_cell_measurement_theta_max     25.08
_cell_measurement_temperature     292(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.467
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     992
_exptl_absorpt_coefficient_mu     0.118
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1997)'
_exptl_absorpt_correction_T_min     0.9655
_exptl_absorpt_correction_T_max     0.9883
_exptl_special_details
;
;
_diffrn_ambient_temperature     292(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 SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11538
_diffrn_reflns_av_R_equivalents     0.0525
_diffrn_reflns_av_sigmaI/netI     0.0440
_diffrn_reflns_theta_min     1.59
_diffrn_reflns_theta_max     26.00
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -31
_diffrn_reflns_limit_k_max     31
_diffrn_reflns_limit_l_min     -10
_diffrn_reflns_limit_l_max     6
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_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 > 2sigma(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     4225
_reflns_number_gt     3284
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0810
_refine_ls_R_factor_gt     0.0647
_refine_ls_wR_factor_gt     0.1611
_refine_ls_wR_factor_ref     0.1719
_refine_ls_goodness_of_fit_ref     1.054
_refine_ls_restrained_S_all     1.054
_refine_ls_number_reflns     4225
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0729P)²+1.0059P] where P = (Fo²+2Fc²)/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     0.000
_refine_diff_density_max     0.484
_refine_diff_density_min     -0.319
_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'
    'O' 'O' 0.0106 0.0060
                         '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'
_computing_data_collection     'SMART (Bruker, 1997)'
_computing_cell_refinement     'SMART'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 2001)'
_computing_publication_material     'SHELXTL'
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
    C1 0.1389(3) 0.42010(13) 0.6095(4) 0.0617(8) Uani d . 1 . . C
    C2 0.0849(3) 0.45554(12) 0.7083(3) 0.0556(7) Uani d . 1 . . C
    H2 0.0287 0.4440 0.7779 0.067 Uiso calc R 1 . . H
    C3 0.2213(3) 0.43524(15) 0.5052(4) 0.0673(9) Uani d . 1 . . C
    H3 0.2560 0.4109 0.4415 0.081 Uiso calc R 1 . . H
    C4 0.2513(3) 0.48671(15) 0.4970(3) 0.0627(8) Uani d . 1 . . C
    H4 0.3065 0.4976 0.4254 0.075 Uiso calc R 1 . . H
    C5 0.2016(3) 0.52406(12) 0.5933(3) 0.0505(7) Uani d . 1 . . C
    C6 0.1168(2) 0.50771(11) 0.7001(3) 0.0465(6) Uani d . 1 . . C
    C7 0.0658(2) 0.54637(11) 0.8104(3) 0.0444(6) Uani d . 1 . . C
    H7A 0.0136 0.5733 0.7475 0.053 Uiso calc R 1 . . H
    H7B 0.0065 0.5285 0.8722 0.053 Uiso calc R 1 . . H
    C8 0.2401(3) 0.58054(13) 0.5820(3) 0.0547(7) Uani d . 1 . . C
    H8A 0.2946 0.5842 0.4983 0.066 Uiso calc R 1 . . H
    H8B 0.1588 0.6011 0.5516 0.066 Uiso calc R 1 . . H
    C9 0.2468(2) 0.54454(10) 1.0469(3) 0.0405(6) Uani d . 1 . . C
    C10 0.4515(2) 0.59340(10) 0.7716(3) 0.0455(6) Uani d . 1 . . C
    C11 0.2515(2) 0.61362(10) 0.8665(3) 0.0411(6) Uani d . 1 . . C
    C12 0.1604(2) 0.66209(11) 0.8355(3) 0.0484(6) Uani d . 1 . . C
    C13 0.0130(3) 0.71658(13) 0.9564(5) 0.0777(10) Uani d . 1 . . C
    H13A 0.0204 0.7328 1.0606 0.093 Uiso calc R 1 . . H
    H13B 0.0363 0.7425 0.8822 0.093 Uiso calc R 1 . . H
    C14 -0.1244(4) 0.6991(2) 0.9051(8) 0.1211(19) Uani d . 1 . . C
    H14A -0.1386 0.6925 0.7924 0.182 Uiso calc R 1 . . H
    H14B -0.1859 0.7257 0.9281 0.182 Uiso calc R 1 . . H
    H14C -0.1398 0.6676 0.9607 0.182 Uiso calc R 1 . . H
    C15 0.3742(2) 0.61854(10) 1.0053(3) 0.0412(6) Uani d . 1 . . C
    C16 0.3883(3) 0.66993(11) 1.0983(4) 0.0517(7) Uani d . 1 . . C
    C17 0.4105(4) 0.76209(12) 1.0753(5) 0.0721(9) Uani d . 1 . . C
    H17A 0.3635 0.7877 1.0022 0.087 Uiso calc R 1 . . H
    H17B 0.3710 0.7626 1.1721 0.087 Uiso calc R 1 . . H
    C18 0.5533(5) 0.77571(18) 1.1127(7) 0.1125(16) Uani d . 1 . . C
    H18A 0.5975 0.7527 1.1942 0.169 Uiso calc R 1 . . H
    H18B 0.5622 0.8112 1.1501 0.169 Uiso calc R 1 . . H
    H18C 0.5939 0.7722 1.0187 0.169 Uiso calc R 1 . . H
    C19 0.4785(3) 0.55311(12) 1.2008(3) 0.0535(7) Uani d . 1 . . C
    H19A 0.5146 0.5773 1.2849 0.064 Uiso calc R 1 . . H
    H19B 0.4564 0.5208 1.2503 0.064 Uiso calc R 1 . . H
    C20 0.6092(2) 0.58940(11) 1.0257(4) 0.0517(7) Uani d . 1 . . C
    H20A 0.6773 0.5816 0.9603 0.062 Uiso calc R 1 . . H
    H20B 0.6463 0.6151 1.1049 0.062 Uiso calc R 1 . . H
    N1 0.1078(4) 0.36465(13) 0.6249(5) 0.0868(9) Uani d . 1 . . N
    N2 0.17610(19) 0.57088(8) 0.9189(2) 0.0394(5) Uani d . 1 . . N
    N3 0.3152(2) 0.60163(9) 0.7303(2) 0.0456(5) Uani d . 1 . . N
    N4 0.35689(19) 0.57505(9) 1.1083(3) 0.0453(5) Uani d . 1 . . N
    N5 0.49109(19) 0.61109(8) 0.9262(3) 0.0431(5) Uani d . 1 . . N
    O1 0.0227(5) 0.35157(13) 0.6997(5) 0.1286(13) Uani d . 1 . . O
    O2 0.1678(5) 0.33316(15) 0.5526(7) 0.168(2) Uani d . 1 . . O
    O3 0.21406(17) 0.50392(8) 1.1014(2) 0.0533(5) Uani d . 1 . . O
    O4 0.52464(19) 0.57600(8) 0.6843(2) 0.0578(5) Uani d . 1 . . O
    O5 0.1399(2) 0.68482(9) 0.7114(3) 0.0756(7) Uani d . 1 . . O
    O6 0.1065(2) 0.67258(8) 0.9643(3) 0.0603(5) Uani d . 1 . . O
    O7 0.3960(3) 0.67188(10) 1.2402(3) 0.0871(8) Uani d . 1 . . O
    O8 0.3943(2) 0.70982(7) 1.0026(2) 0.0593(5) Uani d . 1 . . O
    O9 0.57720(17) 0.54315(8) 1.1034(2) 0.0537(5) Uani d . 1 . . O
_geom_special_details
;
  All esds (except the esd in the dihedral angle between two l.s. planes)
  are estimated using the full covariance matrix.  The cell esds are taken
  into account individually in the estimation of esds in distances, angles
  and torsion angles; correlations between esds in cell parameters are only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds 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
    C1 C3 . 1.364(5) ?
    C1 C2 . 1.403(4) ?
    C1 N1 . 1.462(5) yes
    C2 C6 . 1.376(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.354(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.402(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.406(4) ?
    C5 C8 . 1.502(4) ?
    C6 C7 . 1.509(4) ?
    C7 N2 . 1.461(3) ?
    C7 H7A . 0.9700 ?
    C7 H7B . 0.9700 ?
    C8 N3 . 1.462(4) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 O3 . 1.205(3) yes
    C9 N2 . 1.374(3) yes
    C9 N4 . 1.384(3) yes
    C10 O4 . 1.211(3) yes
    C10 N3 . 1.372(3) yes
    C10 N5 . 1.385(3) yes
    C11 N2 . 1.441(3) yes
    C11 N3 . 1.444(3) yes
    C11 C12 . 1.538(4) ?
    C11 C15 . 1.566(3) yes
    C12 O5 . 1.192(3) ?
    C12 O6 . 1.326(3) ?
    C13 C14 . 1.448(6) ?
    C13 O6 . 1.460(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 N4 . 1.443(3) yes
    C15 N5 . 1.458(3) yes
    C15 C16 . 1.527(4) ?
    C16 O7 . 1.197(4) ?
    C16 O8 . 1.312(3) ?
    C17 C18 . 1.460(6) ?
    C17 O8 . 1.470(4) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
    C19 O9 . 1.415(3) yes
    C19 N4 . 1.452(3) ?
    C19 H19A . 0.9700 ?
    C19 H19B . 0.9700 ?
    C20 O9 . 1.417(3) yes
    C20 N5 . 1.450(3) ?
    C20 H20A . 0.9700 ?
    C20 H20B . 0.9700 ?
    N1 O1 . 1.193(4) ?
    N1 O2 . 1.229(5) ?
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
    C3 C1 C2 . . 122.7(3) ?
    C3 C1 N1 . . 119.7(3) ?
    C2 C1 N1 . . 117.6(3) ?
    C6 C2 C1 . . 118.7(3) ?
    C6 C2 H2 . . 120.7 ?
    C1 C2 H2 . . 120.7 ?
    C4 C3 C1 . . 118.2(3) ?
    C4 C3 H3 . . 120.9 ?
    C1 C3 H3 . . 120.9 ?
    C3 C4 C5 . . 121.9(3) ?
    C3 C4 H4 . . 119.1 ?
    C5 C4 H4 . . 119.1 ?
    C4 C5 C6 . . 119.1(3) ?
    C4 C5 C8 . . 119.8(3) ?
    C6 C5 C8 . . 121.1(3) ?
    C2 C6 C5 . . 119.4(3) ?
    C2 C6 C7 . . 119.9(3) ?
    C5 C6 C7 . . 120.6(3) ?
    N2 C7 C6 . . 111.93(19) yes
    N2 C7 H7A . . 109.2 ?
    C6 C7 H7A . . 109.2 ?
    N2 C7 H7B . . 109.2 ?
    C6 C7 H7B . . 109.2 ?
    H7A C7 H7B . . 107.9 ?
    N3 C8 C5 . . 113.6(2) yes
    N3 C8 H8A . . 108.8 ?
    C5 C8 H8A . . 108.8 ?
    N3 C8 H8B . . 108.8 ?
    C5 C8 H8B . . 108.8 ?
    H8A C8 H8B . . 107.7 ?
    O3 C9 N2 . . 126.0(2) ?
    O3 C9 N4 . . 126.3(2) ?
    N2 C9 N4 . . 107.5(2) yes
    O4 C10 N3 . . 125.4(3) ?
    O4 C10 N5 . . 126.3(2) ?
    N3 C10 N5 . . 108.2(2) yes
    N2 C11 N3 . . 114.3(2) yes
    N2 C11 C12 . . 109.61(19) ?
    N3 C11 C12 . . 111.3(2) ?
    N2 C11 C15 . . 102.53(18) ?
    N3 C11 C15 . . 102.93(18) ?
    C12 C11 C15 . . 116.0(2) ?
    O5 C12 O6 . . 126.7(3) ?
    O5 C12 C11 . . 123.8(3) ?
    O6 C12 C11 . . 109.5(2) ?
    C14 C13 O6 . . 110.5(3) ?
    C14 C13 H13A . . 109.5 ?
    O6 C13 H13A . . 109.5 ?
    C14 C13 H13B . . 109.5 ?
    O6 C13 H13B . . 109.5 ?
    H13A C13 H13B . . 108.1 ?
    C13 C14 H14A . . 109.5 ?
    C13 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    C13 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    N4 C15 N5 . . 111.5(2) yes
    N4 C15 C16 . . 111.0(2) ?
    N5 C15 C16 . . 109.7(2) ?
    N4 C15 C11 . . 103.70(19) ?
    N5 C15 C11 . . 103.62(19) ?
    C16 C15 C11 . . 117.0(2) ?
    O7 C16 O8 . . 126.2(3) ?
    O7 C16 C15 . . 122.8(3) ?
    O8 C16 C15 . . 111.0(2) ?
    C18 C17 O8 . . 110.2(3) ?
    C18 C17 H17A . . 109.6 ?
    O8 C17 H17A . . 109.6 ?
    C18 C17 H17B . . 109.6 ?
    O8 C17 H17B . . 109.6 ?
    H17A C17 H17B . . 108.1 ?
    C17 C18 H18A . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    C17 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
    O9 C19 N4 . . 111.2(2) ?
    O9 C19 H19A . . 109.4 ?
    N4 C19 H19A . . 109.4 ?
    O9 C19 H19B . . 109.4 ?
    N4 C19 H19B . . 109.4 ?
    H19A C19 H19B . . 108.0 ?
    O9 C20 N5 . . 111.40(19) ?
    O9 C20 H20A . . 109.3 ?
    N5 C20 H20A . . 109.3 ?
    O9 C20 H20B . . 109.3 ?
    N5 C20 H20B . . 109.3 ?
    H20A C20 H20B . . 108.0 ?
    O1 N1 O2 . . 122.4(4) ?
    O1 N1 C1 . . 120.1(4) ?
    O2 N1 C1 . . 117.4(4) ?
    C9 N2 C11 . . 112.72(19) ?
    C9 N2 C7 . . 122.0(2) ?
    C11 N2 C7 . . 120.86(19) ?
    C10 N3 C11 . . 112.5(2) ?
    C10 N3 C8 . . 121.0(2) ?
    C11 N3 C8 . . 122.4(2) ?
    C9 N4 C15 . . 111.95(19) ?
    C9 N4 C19 . . 122.4(2) ?
    C15 N4 C19 . . 116.83(19) ?
    C10 N5 C20 . . 120.6(2) ?
    C10 N5 C15 . . 110.65(19) ?
    C20 N5 C15 . . 115.1(2) ?
    C12 O6 C13 . . 117.7(2) ?
    C16 O8 C17 . . 117.4(2) ?
    C19 O9 C20 . . 110.9(2) yes
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 C1 C2 C6 . . . . -0.3(4) ?
    N1 C1 C2 C6 . . . . 177.7(2) ?
    C2 C1 C3 C4 . . . . -0.2(4) ?
    N1 C1 C3 C4 . . . . -178.2(3) ?
    C1 C3 C4 C5 . . . . 0.8(4) ?
    C3 C4 C5 C6 . . . . -0.8(4) ?
    C3 C4 C5 C8 . . . . 178.8(3) ?
    C1 C2 C6 C5 . . . . 0.2(4) ?
    C1 C2 C6 C7 . . . . -177.0(2) ?
    C4 C5 C6 C2 . . . . 0.3(4) ?
    C8 C5 C6 C2 . . . . -179.3(2) ?
    C4 C5 C6 C7 . . . . 177.5(2) ?
    C8 C5 C6 C7 . . . . -2.1(3) ?
    C2 C6 C7 N2 . . . . 116.3(3) ?
    C5 C6 C7 N2 . . . . -60.9(3) ?
    C4 C5 C8 N3 . . . . -118.0(3) ?
    C6 C5 C8 N3 . . . . 61.6(3) ?
    N2 C11 C12 O5 . . . . -123.6(3) ?
    N3 C11 C12 O5 . . . . 3.8(4) ?
    C15 C11 C12 O5 . . . . 121.0(3) ?
    N2 C11 C12 O6 . . . . 54.1(3) ?
    N3 C11 C12 O6 . . . . -178.5(2) ?
    C15 C11 C12 O6 . . . . -61.3(3) ?
    N2 C11 C15 N4 . . . . 5.0(2) ?
    N3 C11 C15 N4 . . . . -113.9(2) ?
    C12 C11 C15 N4 . . . . 124.4(2) ?
    N2 C11 C15 N5 . . . . 121.5(2) ?
    N3 C11 C15 N5 . . . . 2.6(2) ?
    C12 C11 C15 N5 . . . . -119.1(2) ?
    N2 C11 C15 C16 . . . . -117.6(2) ?
    N3 C11 C15 C16 . . . . 123.5(2) ?
    C12 C11 C15 C16 . . . . 1.8(3) ?
    N4 C15 C16 O7 . . . . 6.3(4) ?
    N5 C15 C16 O7 . . . . -117.4(3) ?
    C11 C15 C16 O7 . . . . 125.0(3) ?
    N4 C15 C16 O8 . . . . -175.4(2) ?
    N5 C15 C16 O8 . . . . 60.9(3) ?
    C11 C15 C16 O8 . . . . -56.7(3) ?
    C3 C1 N1 O1 . . . . -170.3(4) ?
    C2 C1 N1 O1 . . . . 11.7(5) ?
    C3 C1 N1 O2 . . . . 6.5(5) ?
    C2 C1 N1 O2 . . . . -171.5(4) ?
    O3 C9 N2 C11 . . . . -170.6(2) ?
    N4 C9 N2 C11 . . . . 13.7(3) ?
    O3 C9 N2 C7 . . . . -14.1(4) ?
    N4 C9 N2 C7 . . . . 170.2(2) ?
    N3 C11 N2 C9 . . . . 99.1(2) ?
    C12 C11 N2 C9 . . . . -135.3(2) ?
    C15 C11 N2 C9 . . . . -11.5(3) ?
    N3 C11 N2 C7 . . . . -57.7(3) ?
    C12 C11 N2 C7 . . . . 68.0(3) ?
    C15 C11 N2 C7 . . . . -168.3(2) ?
    C6 C7 N2 C9 . . . . -74.5(3) yes
    C6 C7 N2 C11 . . . . 80.2(3) yes
    O4 C10 N3 C11 . . . . 169.5(2) ?
    N5 C10 N3 C11 . . . . -13.8(3) ?
    O4 C10 N3 C8 . . . . 11.7(4) ?
    N5 C10 N3 C8 . . . . -171.6(2) ?
    N2 C11 N3 C10 . . . . -103.8(2) ?
    C12 C11 N3 C10 . . . . 131.4(2) ?
    C15 C11 N3 C10 . . . . 6.6(3) ?
    N2 C11 N3 C8 . . . . 53.6(3) ?
    C12 C11 N3 C8 . . . . -71.2(3) ?
    C15 C11 N3 C8 . . . . 164.0(2) ?
    C5 C8 N3 C10 . . . . 81.6(3) yes
    C5 C8 N3 C11 . . . . -73.9(3) yes
    O3 C9 N4 C15 . . . . 174.4(2) ?
    N2 C9 N4 C15 . . . . -9.9(3) ?
    O3 C9 N4 C19 . . . . 28.1(4) ?
    N2 C9 N4 C19 . . . . -156.1(2) ?
    N5 C15 N4 C9 . . . . -108.2(2) ?
    C16 C15 N4 C9 . . . . 129.1(2) ?
    C11 C15 N4 C9 . . . . 2.7(3) ?
    N5 C15 N4 C19 . . . . 40.1(3) ?
    C16 C15 N4 C19 . . . . -82.5(3) ?
    C11 C15 N4 C19 . . . . 151.0(2) ?
    O9 C19 N4 C9 . . . . 95.7(3) ?
    O9 C19 N4 C15 . . . . -49.1(3) ?
    O4 C10 N5 C20 . . . . -29.2(4) ?
    N3 C10 N5 C20 . . . . 154.1(2) ?
    O4 C10 N5 C15 . . . . -167.8(3) ?
    N3 C10 N5 C15 . . . . 15.5(3) ?
    O9 C20 N5 C10 . . . . -85.2(3) ?
    O9 C20 N5 C15 . . . . 51.7(3) ?
    N4 C15 N5 C10 . . . . 100.0(2) ?
    C16 C15 N5 C10 . . . . -136.6(2) ?
    C11 C15 N5 C10 . . . . -11.0(3) ?
    N4 C15 N5 C20 . . . . -41.1(3) ?
    C16 C15 N5 C20 . . . . 82.3(3) ?
    C11 C15 N5 C20 . . . . -152.0(2) ?
    O5 C12 O6 C13 . . . . -0.5(4) ?
    C11 C12 O6 C13 . . . . -178.1(2) ?
    C14 C13 O6 C12 . . . . 91.6(4) ?
    O7 C16 O8 C17 . . . . -0.7(4) ?
    C15 C16 O8 C17 . . . . -178.9(2) ?
    C18 C17 O8 C16 . . . . 92.4(4) ?
    N4 C19 O9 C20 . . . . 57.5(3) ?
    N5 C20 O9 C19 . . . . -59.4(3) ?
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
    C20 H20A O3 3_667 0.97 2.54 3.262(4) 132
    C19 H19B O4 3_667 0.97 2.54 3.444(4) 156
    C17 H17A O7 4_575 0.97 2.52 3.293(5) 136
    C7 H7B O3 3_567 0.97 2.41 3.288(3) 150
