##############################################################################
###                                                                        ###
###        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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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-10-27
_journal_date_accepted     2009-10-28
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2950
_journal_page_last     o2950
_journal_paper_category     QO
_journal_coeditor_code     HB5194
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 4204 '
_publ_section_title
;
4,4'-Bipyridine--pyroglutamic acid (1/2)
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Arman, Hadi D.' .
;
Department of Chemistry, The University of Texas at San Antonio,
One UTSA Circle, San Antonio, Texas 78249-0698, USA
;
    'Kaulgud, Trupta' .
;
Department of Chemistry, The University of Texas at San Antonio,
One UTSA Circle, San Antonio, Texas 78249-0698, USA
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4,4'-Bipyridine--pyroglutamic acid (1/2)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C10 H8 N2, 2(C5 H7 N O3)'
_chemical_formula_sum     'C20 H22 N4 O6'
_chemical_formula_iupac     'C10 H8 N2, 2C5 H7 N O3'
_chemical_formula_weight     414.42
_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     7.444(3)
_cell_length_b     11.511(4)
_cell_length_c     12.845(4)
_cell_angle_alpha     66.274(17)
_cell_angle_beta     74.203(17)
_cell_angle_gamma     86.91(2)
_cell_volume     967.6(6)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3819
_cell_measurement_theta_min     1.8
_cell_measurement_theta_max     40.3
_cell_measurement_temperature     98(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.22
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.12
_exptl_crystal_density_diffrn     1.422
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.107
_exptl_absorpt_correction_type     'Multi-scan'
_exptl_absorpt_process_details     '(ABSCOR; Higashi, 1995)'
_exptl_absorpt_correction_T_min     0.706
_exptl_absorpt_correction_T_max     1.000
_exptl_special_details
;
;
_diffrn_ambient_temperature     98(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type
;
Rigaku Saturn724
;
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     28.5714
_diffrn_reflns_number     5618
_diffrn_reflns_av_R_equivalents     0.041
_diffrn_reflns_av_sigmaI/netI     0.060
_diffrn_reflns_theta_min     1.8
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.993
_diffrn_measured_fraction_theta_full     0.993
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     '<1'
_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 >
2σ(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     3375
_reflns_number_gt     2851
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.068
_refine_ls_R_factor_gt     0.056
_refine_ls_wR_factor_gt     0.121
_refine_ls_wR_factor_ref     0.128
_refine_ls_goodness_of_fit_ref     1.16
_refine_ls_restrained_S_all     1.16
_refine_ls_number_reflns     3375
_refine_ls_number_parameters     281
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0416P)²+0.3826P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.29
_refine_diff_density_min     -0.26
_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     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction     'CrystalClear (Rigaku/MSC, 2005)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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 0.7958(3) 0.80500(15) 0.34215(15) 0.0306(4) Uani d . 1 . .
    H H1o 0.8071 0.7262 0.3706 0.046 Uiso calc R 1 . .
    O O2 0.7021(3) 0.76264(15) 0.20917(14) 0.0300(4) Uani d . 1 . .
    O O3 0.6914(2) 1.13445(15) -0.10317(14) 0.0250(4) Uani d . 1 . .
    O O4 0.6382(2) -0.34079(15) 0.69099(15) 0.0295(4) Uani d . 1 . .
    H H4o 0.6741 -0.2635 0.6605 0.044 Uiso calc R 1 . .
    O O5 0.3864(2) -0.27410(15) 0.78866(14) 0.0278(4) Uani d . 1 . .
    O O6 0.0822(2) -0.65238(15) 1.10646(14) 0.0263(4) Uani d . 1 . .
    N N1 0.6307(3) 1.00631(18) 0.09308(17) 0.0239(5) Uani d D 1 . .
    H H1N 0.5362 0.9583 0.1002 0.027(7) Uiso d D 1 . .
    N N2 0.2248(3) -0.51418(18) 0.91661(17) 0.0233(5) Uani d D 1 . .
    H H2N 0.1380 -0.4596 0.9022 0.028(7) Uiso d D 1 . .
    N N3 0.8270(3) 0.56170(18) 0.42251(18) 0.0266(5) Uani d . 1 . .
    N N4 0.7503(3) -0.10455(18) 0.60996(17) 0.0247(5) Uani d . 1 . .
    C C1 0.7328(3) 0.8368(2) 0.24872(19) 0.0217(5) Uani d . 1 . .
    C C2 0.7041(3) 0.9777(2) 0.19365(19) 0.0215(5) Uani d . 1 . .
    H H2 0.6154 1.0033 0.2536 0.026 Uiso calc R 1 . .
    C C3 0.7237(3) 1.1014(2) -0.0062(2) 0.0218(5) Uani d . 1 . .
    C C4 0.8716(3) 1.1608(2) 0.02102(19) 0.0228(5) Uani d . 1 . .
    H H4A 0.8325 1.2423 0.0263 0.027 Uiso calc R 1 . .
    H H4B 0.9921 1.1764 -0.0406 0.027 Uiso calc R 1 . .
    C C5 0.8887(3) 1.0625(2) 0.1407(2) 0.0225(5) Uani d . 1 . .
    H H5A 0.9011 1.1045 0.1924 0.027 Uiso calc R 1 . .
    H H5B 0.9984 1.0116 0.1302 0.027 Uiso calc R 1 . .
    C C6 0.4717(3) -0.3581(2) 0.76693(19) 0.0219(5) Uani d . 1 . .
    C C7 0.3977(3) -0.4950(2) 0.82374(19) 0.0213(5) Uani d . 1 . .
    H H7 0.3747 -0.5203 0.7624 0.026 Uiso calc R 1 . .
    C C8 0.2141(3) -0.6187(2) 1.0153(2) 0.0214(5) Uani d . 1 . .
    C C9 0.3900(3) -0.6883(2) 0.9955(2) 0.0236(5) Uani d . 1 . .
    H H9A 0.3657 -0.7619 0.9788 0.028 Uiso calc R 1 . .
    H H9B 0.4397 -0.7187 1.0655 0.028 Uiso calc R 1 . .
    C C10 0.5264(3) -0.5884(2) 0.8884(2) 0.0248(5) Uani d . 1 . .
    H H10A 0.6061 -0.6274 0.8373 0.030 Uiso calc R 1 . .
    H H10B 0.6074 -0.5452 0.9133 0.030 Uiso calc R 1 . .
    C C11 0.9039(3) 0.5073(2) 0.3470(2) 0.0268(6) Uani d . 1 . .
    H H11 0.9653 0.5605 0.2674 0.032 Uiso calc R 1 . .
    C C12 0.8973(3) 0.3770(2) 0.3805(2) 0.0243(5) Uani d . 1 . .
    H H12 0.9549 0.3417 0.3251 0.029 Uiso calc R 1 . .
    C C13 0.8049(3) 0.2985(2) 0.4965(2) 0.0223(5) Uani d . 1 . .
    C C14 0.7272(3) 0.3554(2) 0.5749(2) 0.0253(5) Uani d . 1 . .
    H H14 0.6659 0.3047 0.6552 0.030 Uiso calc R 1 . .
    C C15 0.7406(3) 0.4857(2) 0.5344(2) 0.0273(6) Uani d . 1 . .
    H H15 0.6860 0.5234 0.5883 0.033 Uiso calc R 1 . .
    C C16 0.7879(3) 0.1585(2) 0.5364(2) 0.0208(5) Uani d . 1 . .
    C C17 0.7629(3) 0.1045(2) 0.4611(2) 0.0254(5) Uani d . 1 . .
    H H17 0.7590 0.1570 0.3829 0.030 Uiso calc R 1 . .
    C C18 0.7440(3) -0.0258(2) 0.5017(2) 0.0259(6) Uani d . 1 . .
    H H18 0.7256 -0.0613 0.4500 0.031 Uiso calc R 1 . .
    C C19 0.7758(3) -0.0528(2) 0.6826(2) 0.0258(5) Uani d . 1 . .
    H H19 0.7810 -0.1079 0.7600 0.031 Uiso calc R 1 . .
    C C20 0.7947(3) 0.0765(2) 0.6494(2) 0.0242(5) Uani d . 1 . .
    H H20 0.8121 0.1093 0.7032 0.029 Uiso calc R 1 . .
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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 . 1.314(3) ?
    O1 H1o . 0.8400 ?
    O2 C1 . 1.213(3) ?
    O3 C3 . 1.235(3) ?
    O4 C6 . 1.319(3) ?
    O4 H4o . 0.8400 ?
    O5 C6 . 1.213(3) ?
    O6 C8 . 1.239(3) ?
    N1 C3 . 1.335(3) ?
    N1 C2 . 1.449(3) ?
    N1 H1N . 0.8800 ?
    N2 C8 . 1.338(3) ?
    N2 C7 . 1.453(3) ?
    N2 H2N . 0.8800 ?
    N3 C15 . 1.338(3) ?
    N3 C11 . 1.345(3) ?
    N4 C18 . 1.332(3) ?
    N4 C19 . 1.349(3) ?
    C1 C2 . 1.517(3) ?
    C2 C5 . 1.550(3) ?
    C2 H2 . 1.0000 ?
    C3 C4 . 1.511(3) ?
    C4 C5 . 1.533(3) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.506(3) ?
    C7 C10 . 1.538(3) ?
    C7 H7 . 1.0000 ?
    C8 C9 . 1.514(3) ?
    C9 C10 . 1.529(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.383(3) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.391(3) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.397(3) ?
    C13 C16 . 1.482(3) ?
    C14 C15 . 1.374(3) ?
    C14 H14 . 0.9500 ?
    C15 H15 . 0.9500 ?
    C16 C20 . 1.390(3) ?
    C16 C17 . 1.396(3) ?
    C17 C18 . 1.377(3) ?
    C17 H17 . 0.9500 ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.376(3) ?
    C19 H19 . 0.9500 ?
    C20 H20 . 0.9500 ?
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
    C1 O1 H1o . . 109.5 ?
    C6 O4 H4o . . 109.5 ?
    C3 N1 C2 . . 115.02(18) ?
    C3 N1 H1N . . 125.7 ?
    C2 N1 H1N . . 119.2 ?
    C8 N2 C7 . . 114.5(2) ?
    C8 N2 H2N . . 127.0 ?
    C7 N2 H2N . . 118.5 ?
    C15 N3 C11 . . 118.1(2) ?
    C18 N4 C19 . . 117.74(19) ?
    O2 C1 O1 . . 124.3(2) ?
    O2 C1 C2 . . 123.0(2) ?
    O1 C1 C2 . . 112.71(18) ?
    N1 C2 C1 . . 110.12(18) ?
    N1 C2 C5 . . 103.77(17) ?
    C1 C2 C5 . . 113.37(19) ?
    N1 C2 H2 . . 109.8 ?
    C1 C2 H2 . . 109.8 ?
    C5 C2 H2 . . 109.8 ?
    O3 C3 N1 . . 124.9(2) ?
    O3 C3 C4 . . 126.5(2) ?
    N1 C3 C4 . . 108.55(19) ?
    C3 C4 C5 . . 104.45(18) ?
    C3 C4 H4A . . 110.9 ?
    C5 C4 H4A . . 110.9 ?
    C3 C4 H4B . . 110.9 ?
    C5 C4 H4B . . 110.9 ?
    H4A C4 H4B . . 108.9 ?
    C4 C5 C2 . . 104.29(17) ?
    C4 C5 H5A . . 110.9 ?
    C2 C5 H5A . . 110.9 ?
    C4 C5 H5B . . 110.9 ?
    C2 C5 H5B . . 110.9 ?
    H5A C5 H5B . . 108.9 ?
    O5 C6 O4 . . 124.4(2) ?
    O5 C6 C7 . . 123.4(2) ?
    O4 C6 C7 . . 112.18(19) ?
    N2 C7 C6 . . 111.09(19) ?
    N2 C7 C10 . . 103.22(18) ?
    C6 C7 C10 . . 114.16(19) ?
    N2 C7 H7 . . 109.4 ?
    C6 C7 H7 . . 109.4 ?
    C10 C7 H7 . . 109.4 ?
    O6 C8 N2 . . 125.7(2) ?
    O6 C8 C9 . . 126.3(2) ?
    N2 C8 C9 . . 108.0(2) ?
    C8 C9 C10 . . 104.03(18) ?
    C8 C9 H9A . . 111.0 ?
    C10 C9 H9A . . 111.0 ?
    C8 C9 H9B . . 111.0 ?
    C10 C9 H9B . . 111.0 ?
    H9A C9 H9B . . 109.0 ?
    C9 C10 C7 . . 103.70(19) ?
    C9 C10 H10A . . 111.0 ?
    C7 C10 H10A . . 111.0 ?
    C9 C10 H10B . . 111.0 ?
    C7 C10 H10B . . 111.0 ?
    H10A C10 H10B . . 109.0 ?
    N3 C11 C12 . . 122.7(2) ?
    N3 C11 H11 . . 118.6 ?
    C12 C11 H11 . . 118.6 ?
    C11 C12 C13 . . 119.0(2) ?
    C11 C12 H12 . . 120.5 ?
    C13 C12 H12 . . 120.5 ?
    C12 C13 C14 . . 118.0(2) ?
    C12 C13 C16 . . 121.4(2) ?
    C14 C13 C16 . . 120.6(2) ?
    C15 C14 C13 . . 119.3(2) ?
    C15 C14 H14 . . 120.4 ?
    C13 C14 H14 . . 120.4 ?
    N3 C15 C14 . . 122.9(2) ?
    N3 C15 H15 . . 118.5 ?
    C14 C15 H15 . . 118.5 ?
    C20 C16 C17 . . 117.6(2) ?
    C20 C16 C13 . . 121.71(19) ?
    C17 C16 C13 . . 120.7(2) ?
    C18 C17 C16 . . 119.2(2) ?
    C18 C17 H17 . . 120.4 ?
    C16 C17 H17 . . 120.4 ?
    N4 C18 C17 . . 123.2(2) ?
    N4 C18 H18 . . 118.4 ?
    C17 C18 H18 . . 118.4 ?
    N4 C19 C20 . . 122.7(2) ?
    N4 C19 H19 . . 118.6 ?
    C20 C19 H19 . . 118.6 ?
    C19 C20 C16 . . 119.5(2) ?
    C19 C20 H20 . . 120.3 ?
    C16 C20 H20 . . 120.3 ?
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 N1 C2 C1 . . . . -128.8(2) ?
    C3 N1 C2 C5 . . . . -7.2(3) ?
    O2 C1 C2 N1 . . . . 2.0(3) ?
    O1 C1 C2 N1 . . . . -178.66(19) ?
    O2 C1 C2 C5 . . . . -113.8(2) ?
    O1 C1 C2 C5 . . . . 65.6(3) ?
    C2 N1 C3 O3 . . . . 174.8(2) ?
    C2 N1 C3 C4 . . . . -5.7(3) ?
    O3 C3 C4 C5 . . . . -164.3(2) ?
    N1 C3 C4 C5 . . . . 16.1(2) ?
    C3 C4 C5 C2 . . . . -19.6(2) ?
    N1 C2 C5 C4 . . . . 16.5(2) ?
    C1 C2 C5 C4 . . . . 135.96(19) ?
    C8 N2 C7 C6 . . . . -136.67(19) ?
    C8 N2 C7 C10 . . . . -13.9(2) ?
    O5 C6 C7 N2 . . . . -7.0(3) ?
    O4 C6 C7 N2 . . . . 173.39(18) ?
    O5 C6 C7 C10 . . . . -123.2(2) ?
    O4 C6 C7 C10 . . . . 57.2(3) ?
    C7 N2 C8 O6 . . . . 178.2(2) ?
    C7 N2 C8 C9 . . . . -2.1(2) ?
    O6 C8 C9 C10 . . . . -163.0(2) ?
    N2 C8 C9 C10 . . . . 17.4(2) ?
    C8 C9 C10 C7 . . . . -24.8(2) ?
    N2 C7 C10 C9 . . . . 23.4(2) ?
    C6 C7 C10 C9 . . . . 144.11(19) ?
    C15 N3 C11 C12 . . . . -0.1(3) ?
    N3 C11 C12 C13 . . . . 1.1(3) ?
    C11 C12 C13 C14 . . . . -1.8(3) ?
    C11 C12 C13 C16 . . . . 178.0(2) ?
    C12 C13 C14 C15 . . . . 1.6(3) ?
    C16 C13 C14 C15 . . . . -178.1(2) ?
    C11 N3 C15 C14 . . . . 0.0(3) ?
    C13 C14 C15 N3 . . . . -0.7(4) ?
    C12 C13 C16 C20 . . . . 144.2(2) ?
    C14 C13 C16 C20 . . . . -36.0(3) ?
    C12 C13 C16 C17 . . . . -36.3(3) ?
    C14 C13 C16 C17 . . . . 143.4(2) ?
    C20 C16 C17 C18 . . . . 0.8(3) ?
    C13 C16 C17 C18 . . . . -178.7(2) ?
    C19 N4 C18 C17 . . . . 0.2(4) ?
    C16 C17 C18 N4 . . . . -0.7(4) ?
    C18 N4 C19 C20 . . . . 0.2(4) ?
    N4 C19 C20 C16 . . . . -0.2(4) ?
    C17 C16 C20 C19 . . . . -0.3(3) ?
    C13 C16 C20 C19 . . . . 179.2(2) ?
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
    O1 H1o N3 1_555 0.84 1.75 2.588(3) 177 y
    O4 H4o N4 1_555 0.84 1.75 2.582(3) 175 y
    N1 H1n O3 2_675 0.88 2.03 2.911(3) 174 y
    N2 H2n O6 2_547 0.88 2.03 2.903(3) 172 y
    C15 H15 O4 1_565 0.95 2.38 3.294(3) 162 y
    C18 H18 O1 1_545 0.95 2.41 3.293(3) 155 y
