##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, 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          #
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#                                                                            #
# 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     2007-12-11
_journal_date_accepted     2008-01-25
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2008
_journal_volume     64
_journal_issue      3
_journal_page_first     o139
_journal_page_last     o141
_journal_paper_category     FO
_journal_coeditor_code     AV3135
_publ_contact_author
;
Frank R. Fronczek
Department of Chemistry
Louisiana State University
Baton Rouge
LA  70803-1804
USA
;
_publ_contact_author_email     ffroncz@lsu.edu
_publ_contact_author_fax     '(225) 578 3458'
_publ_contact_author_phone     '(225) 578 8270'
_publ_section_title
;
Cyclopentadecanone 2,4-dinitrophenylhydrazone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Noe, Eric A.' .
;
     Department of Chemistry
     Jackson State University
     1400 J. R. Lynch Street
     Jackson
     MS 39217-0510
     USA
;
    'Pawar, Diwakar M.' .
;
     Department of Chemistry
     Jackson State University
     1400 J. R. Lynch Street
     Jackson
     MS 39217-0510
     USA
;
    'Fronczek, Frank R.' .
;    Department of Chemistry
     Louisiana State University
     Baton Rouge
     LA 70803-1804
     USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Cyclopentadecanone 2,4-dinitrophenylhydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H32 N4 O4'
_chemical_formula_sum     'C21 H32 N4 O4'
_chemical_formula_iupac     'C21 H32 N4 O4'
_chemical_formula_weight     404.51
_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     7.2486(14)
_cell_length_b     8.3234(15)
_cell_length_c     17.731(3)
_cell_angle_alpha     103.419(12)
_cell_angle_beta     94.044(9)
_cell_angle_gamma     97.017(13)
_cell_volume     1027.3(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4123
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     29.3
_cell_measurement_temperature     90
_exptl_crystal_description     lath
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.33
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.308
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     90
_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
                  'Nonius KappaCCD with an Oxford Cryosystems Cryostream cooler'
_diffrn_measurement_method     'ω scans with κ offsets'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16738
_diffrn_reflns_av_R_equivalents     0.038
_diffrn_reflns_av_sigmaI/netI     0.0663
_diffrn_reflns_theta_min     2.8
_diffrn_reflns_theta_max     29.3
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.875
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -23
_diffrn_reflns_limit_l_max     23
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     <2
_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     4936
_reflns_number_gt     3372
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.091
_refine_ls_R_factor_gt     0.051
_refine_ls_wR_factor_gt     0.092
_refine_ls_wR_factor_ref     0.104
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     4936
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0302P)²+0.5298P] 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     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.37
_refine_diff_density_min     -0.24
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0153(16)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'COLLECT (Nonius, 2000)'
_computing_cell_refinement     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction     'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al.,  1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_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 0.87072(16) 0.10477(14) 0.48047(7) 0.0192(3) Uani d . 1 . .
    O O2 0.82365(18) 0.18914(16) 0.37503(7) 0.0236(3) Uani d . 1 . .
    O O3 0.28483(19) 0.41631(16) 0.31370(7) 0.0272(3) Uani d . 1 . .
    O O4 0.10538(18) 0.49862(15) 0.40401(8) 0.0252(3) Uani d . 1 . .
    N N1 0.56818(19) 0.14734(16) 0.65874(8) 0.0139(3) Uani d . 1 . .
    N N2 0.6406(2) 0.15332(17) 0.58880(8) 0.0135(3) Uani d . 1 . .
    H H2N 0.745(3) 0.117(2) 0.5767(10) 0.016 Uiso d . 1 . .
    N N3 0.77557(19) 0.16912(16) 0.43770(8) 0.0144(3) Uani d . 1 . .
    N N4 0.2347(2) 0.42481(17) 0.37939(9) 0.0186(3) Uani d . 1 . .
    C C1 0.6738(2) 0.10401(19) 0.70983(9) 0.0135(3) Uani d . 1 . .
    C C2 0.5831(2) 0.0806(2) 0.78126(9) 0.0168(4) Uani d . 1 . .
    H H2A 0.5843 -0.0365 0.7845 0.020 Uiso calc R 1 . .
    H H2B 0.4508 0.0977 0.7744 0.020 Uiso calc R 1 . .
    C C3 0.6735(2) 0.1958(2) 0.85892(9) 0.0161(4) Uani d . 1 . .
    H H3A 0.6269 0.1504 0.9020 0.019 Uiso calc R 1 . .
    H H3B 0.8102 0.1951 0.8616 0.019 Uiso calc R 1 . .
    C C4 0.6354(2) 0.3759(2) 0.87123(10) 0.0165(4) Uani d . 1 . .
    H H4A 0.4991 0.3783 0.8708 0.020 Uiso calc R 1 . .
    H H4B 0.6790 0.4216 0.8277 0.020 Uiso calc R 1 . .
    C C5 0.7340(2) 0.4855(2) 0.94836(10) 0.0179(4) Uani d . 1 . .
    H H5A 0.8694 0.4781 0.9491 0.021 Uiso calc R 1 . .
    H H5B 0.6876 0.4397 0.9914 0.021 Uiso calc R 1 . .
    C C6 0.7079(3) 0.6702(2) 0.96427(10) 0.0202(4) Uani d . 1 . .
    H H6A 0.5732 0.6773 0.9547 0.024 Uiso calc R 1 . .
    H H6B 0.7477 0.7234 1.0200 0.024 Uiso calc R 1 . .
    C C7 0.8160(2) 0.7686(2) 0.91478(10) 0.0188(4) Uani d . 1 . .
    H H7A 0.7699 0.8774 0.9197 0.023 Uiso calc R 1 . .
    H H7B 0.7912 0.7067 0.8594 0.023 Uiso calc R 1 . .
    C C8 1.0267(2) 0.7994(2) 0.93815(10) 0.0170(4) Uani d . 1 . .
    H H8A 1.0697 0.6914 0.9392 0.020 Uiso calc R 1 . .
    H H8B 1.0519 0.8719 0.9916 0.020 Uiso calc R 1 . .
    C C9 1.1408(3) 0.8806(2) 0.88389(10) 0.0177(4) Uani d . 1 . .
    H H9A 1.2691 0.9222 0.9095 0.021 Uiso calc R 1 . .
    H H9B 1.0838 0.9777 0.8750 0.021 Uiso calc R 1 . .
    C C10 1.1509(2) 0.7599(2) 0.80525(10) 0.0177(4) Uani d . 1 . .
    H H10A 1.1948 0.8246 0.7680 0.021 Uiso calc R 1 . .
    H H10B 1.0239 0.7011 0.7846 0.021 Uiso calc R 1 . .
    C C11 1.2819(2) 0.6303(2) 0.81037(10) 0.0178(4) Uani d . 1 . .
    H H11A 1.4118 0.6807 0.8083 0.021 Uiso calc R 1 . .
    H H11B 1.2756 0.6013 0.8613 0.021 Uiso calc R 1 . .
    C C12 1.2348(2) 0.4698(2) 0.74518(10) 0.0161(4) Uani d . 1 . .
    H H12A 1.2054 0.4999 0.6953 0.019 Uiso calc R 1 . .
    H H12B 1.3462 0.4117 0.7402 0.019 Uiso calc R 1 . .
    C C13 1.0700(2) 0.3500(2) 0.75891(10) 0.0164(4) Uani d . 1 . .
    H H13A 1.1003 0.3163 0.8078 0.020 Uiso calc R 1 . .
    H H13B 0.9587 0.4082 0.7650 0.020 Uiso calc R 1 . .
    C C14 1.0251(2) 0.1951(2) 0.69174(9) 0.0149(3) Uani d . 1 . .
    H H14A 1.1406 0.1437 0.6837 0.018 Uiso calc R 1 . .
    H H14B 0.9894 0.2307 0.6439 0.018 Uiso calc R 1 . .
    C C15 0.8694(2) 0.0602(2) 0.70121(10) 0.0155(4) Uani d . 1 . .
    H H15A 0.8616 -0.0356 0.6554 0.019 Uiso calc R 1 . .
    H H15B 0.9095 0.0210 0.7476 0.019 Uiso calc R 1 . .
    C C16 0.5419(2) 0.21265(19) 0.53597(9) 0.0122(3) Uani d . 1 . .
    C C17 0.6019(2) 0.22337(19) 0.46248(9) 0.0131(3) Uani d . 1 . .
    C C18 0.5001(2) 0.28929(19) 0.41090(9) 0.0141(3) Uani d . 1 . .
    H H18 0.5424 0.2945 0.3619 0.017 Uiso calc R 1 . .
    C C19 0.3366(2) 0.3470(2) 0.43182(10) 0.0154(4) Uani d . 1 . .
    C C20 0.2703(2) 0.33826(19) 0.50314(10) 0.0158(4) Uani d . 1 . .
    H H20 0.1567 0.3783 0.5165 0.019 Uiso calc R 1 . .
    C C21 0.3707(2) 0.27143(19) 0.55347(10) 0.0145(3) Uani d . 1 . .
    H H21 0.3243 0.2643 0.6015 0.017 Uiso calc R 1 . .
_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
    O1 N3 . 1.2420(17) ?
    O2 N3 . 1.2289(17) ?
    O3 N4 . 1.2334(19) ?
    O4 N4 . 1.2329(18) ?
    N1 C1 . 1.288(2) y
    N1 N2 . 1.3891(19) y
    N2 C16 . 1.356(2) y
    N2 H2N . 0.869(18) ?
    N3 C17 . 1.451(2) ?
    N4 C19 . 1.459(2) ?
    C1 C2 . 1.508(2) ?
    C1 C15 . 1.516(2) ?
    C2 C3 . 1.533(2) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.526(2) ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C4 C5 . 1.529(2) ?
    C4 H4A . 0.9900 ?
    C4 H4B . 0.9900 ?
    C5 C6 . 1.535(2) ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C6 C7 . 1.526(2) ?
    C6 H6A . 0.9900 ?
    C6 H6B . 0.9900 ?
    C7 C8 . 1.529(2) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 C9 . 1.531(2) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.530(2) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.535(2) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C12 . 1.534(2) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.531(2) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.522(2) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.539(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C21 . 1.417(2) ?
    C16 C17 . 1.421(2) ?
    C17 C18 . 1.385(2) ?
    C18 C19 . 1.375(2) ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.399(2) ?
    C20 C21 . 1.369(2) ?
    C20 H20 . 0.9500 ?
    C21 H21 . 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 N1 N2 . . 116.64(14) y
    C16 N2 N1 . . 118.84(13) y
    C16 N2 H2N . . 118.5(12) ?
    N1 N2 H2N . . 122.7(12) ?
    O2 N3 O1 . . 122.26(13) ?
    O2 N3 C17 . . 118.65(13) ?
    O1 N3 C17 . . 119.08(13) ?
    O4 N4 O3 . . 123.67(14) ?
    O4 N4 C19 . . 117.92(14) ?
    O3 N4 C19 . . 118.39(14) ?
    N1 C1 C2 . . 115.12(15) ?
    N1 C1 C15 . . 126.35(15) ?
    C2 C1 C15 . . 118.28(14) ?
    C1 C2 C3 . . 115.75(14) ?
    C1 C2 H2A . . 108.3 ?
    C3 C2 H2A . . 108.3 ?
    C1 C2 H2B . . 108.3 ?
    C3 C2 H2B . . 108.3 ?
    H2A C2 H2B . . 107.4 ?
    C4 C3 C2 . . 114.20(13) ?
    C4 C3 H3A . . 108.7 ?
    C2 C3 H3A . . 108.7 ?
    C4 C3 H3B . . 108.7 ?
    C2 C3 H3B . . 108.7 ?
    H3A C3 H3B . . 107.6 ?
    C3 C4 C5 . . 111.68(14) ?
    C3 C4 H4A . . 109.3 ?
    C5 C4 H4A . . 109.3 ?
    C3 C4 H4B . . 109.3 ?
    C5 C4 H4B . . 109.3 ?
    H4A C4 H4B . . 107.9 ?
    C4 C5 C6 . . 115.09(14) ?
    C4 C5 H5A . . 108.5 ?
    C6 C5 H5A . . 108.5 ?
    C4 C5 H5B . . 108.5 ?
    C6 C5 H5B . . 108.5 ?
    H5A C5 H5B . . 107.5 ?
    C7 C6 C5 . . 114.39(14) ?
    C7 C6 H6A . . 108.7 ?
    C5 C6 H6A . . 108.7 ?
    C7 C6 H6B . . 108.7 ?
    C5 C6 H6B . . 108.7 ?
    H6A C6 H6B . . 107.6 ?
    C6 C7 C8 . . 112.98(14) ?
    C6 C7 H7A . . 109.0 ?
    C8 C7 H7A . . 109.0 ?
    C6 C7 H7B . . 109.0 ?
    C8 C7 H7B . . 109.0 ?
    H7A C7 H7B . . 107.8 ?
    C7 C8 C9 . . 114.12(14) ?
    C7 C8 H8A . . 108.7 ?
    C9 C8 H8A . . 108.7 ?
    C7 C8 H8B . . 108.7 ?
    C9 C8 H8B . . 108.7 ?
    H8A C8 H8B . . 107.6 ?
    C8 C9 C10 . . 112.57(14) ?
    C8 C9 H9A . . 109.1 ?
    C10 C9 H9A . . 109.1 ?
    C8 C9 H9B . . 109.1 ?
    C10 C9 H9B . . 109.1 ?
    H9A C9 H9B . . 107.8 ?
    C9 C10 C11 . . 113.02(14) ?
    C9 C10 H10A . . 109.0 ?
    C11 C10 H10A . . 109.0 ?
    C9 C10 H10B . . 109.0 ?
    C11 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    C12 C11 C10 . . 113.54(14) ?
    C12 C11 H11A . . 108.9 ?
    C10 C11 H11A . . 108.9 ?
    C12 C11 H11B . . 108.9 ?
    C10 C11 H11B . . 108.9 ?
    H11A C11 H11B . . 107.7 ?
    C13 C12 C11 . . 113.54(14) ?
    C13 C12 H12A . . 108.9 ?
    C11 C12 H12A . . 108.9 ?
    C13 C12 H12B . . 108.9 ?
    C11 C12 H12B . . 108.9 ?
    H12A C12 H12B . . 107.7 ?
    C14 C13 C12 . . 111.64(14) ?
    C14 C13 H13A . . 109.3 ?
    C12 C13 H13A . . 109.3 ?
    C14 C13 H13B . . 109.3 ?
    C12 C13 H13B . . 109.3 ?
    H13A C13 H13B . . 108.0 ?
    C13 C14 C15 . . 116.41(14) ?
    C13 C14 H14A . . 108.2 ?
    C15 C14 H14A . . 108.2 ?
    C13 C14 H14B . . 108.2 ?
    C15 C14 H14B . . 108.2 ?
    H14A C14 H14B . . 107.3 ?
    C1 C15 C14 . . 118.89(13) ?
    C1 C15 H15A . . 107.6 ?
    C14 C15 H15A . . 107.6 ?
    C1 C15 H15B . . 107.6 ?
    C14 C15 H15B . . 107.6 ?
    H15A C15 H15B . . 107.0 ?
    N2 C16 C21 . . 119.99(14) ?
    N2 C16 C17 . . 123.59(14) ?
    C21 C16 C17 . . 116.41(14) ?
    C18 C17 C16 . . 121.98(15) ?
    C18 C17 N3 . . 116.03(14) ?
    C16 C17 N3 . . 121.98(14) ?
    C19 C18 C17 . . 118.87(15) ?
    C19 C18 H18 . . 120.6 ?
    C17 C18 H18 . . 120.6 ?
    C18 C19 C20 . . 121.52(15) ?
    C18 C19 N4 . . 118.87(15) ?
    C20 C19 N4 . . 119.57(14) ?
    C21 C20 C19 . . 119.28(15) ?
    C21 C20 H20 . . 120.4 ?
    C19 C20 H20 . . 120.4 ?
    C20 C21 C16 . . 121.92(15) ?
    C20 C21 H21 . . 119.0 ?
    C16 C21 H21 . . 119.0 ?
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
    C15 C1 C2 C3 . . . . 66.69(18) y
    C1 C2 C3 C4 . . . . 73.82(18) y
    C2 C3 C4 C5 . . . . -178.22(14) y
    C3 C4 C5 C6 . . . . 178.25(15) y
    C4 C5 C6 C7 . . . . -72.9(2) y
    C5 C6 C7 C8 . . . . -71.38(19) y
    C6 C7 C8 C9 . . . . 173.55(14) y
    C7 C8 C9 C10 . . . . -72.99(18) y
    C8 C9 C10 C11 . . . . -74.00(19) y
    C9 C10 C11 C12 . . . . 155.55(15) y
    C10 C11 C12 C13 . . . . -78.94(18) y
    C11 C12 C13 C14 . . . . 178.42(14) y
    C12 C13 C14 C15 . . . . 176.39(14) y
    C14 C15 C1 C2 . . . . -122.89(16) y
    C13 C14 C15 C1 . . . . 61.5(2) y
    N1 C1 C15 C14 . . . . 63.3(2) y
    C1 N1 N2 C16 . . . . -174.11(15) y
    N2 N1 C1 C2 . . . . -173.57(13) ?
    N2 N1 C1 C15 . . . . 0.4(2) ?
    N1 C1 C2 C3 . . . . -118.78(16) ?
    N1 N2 C16 C21 . . . . 1.7(2) ?
    N1 N2 C16 C17 . . . . -179.59(14) ?
    N2 C16 C17 C18 . . . . -178.05(16) ?
    C21 C16 C17 C18 . . . . 0.7(2) ?
    N2 C16 C17 N3 . . . . 0.6(2) ?
    C21 C16 C17 N3 . . . . 179.36(14) ?
    O2 N3 C17 C18 . . . . 2.2(2) ?
    O1 N3 C17 C18 . . . . -178.08(14) ?
    O2 N3 C17 C16 . . . . -176.59(15) ?
    O1 N3 C17 C16 . . . . 3.2(2) ?
    C16 C17 C18 C19 . . . . 0.4(2) ?
    N3 C17 C18 C19 . . . . -178.32(14) ?
    C17 C18 C19 C20 . . . . -0.9(2) ?
    C17 C18 C19 N4 . . . . 176.66(15) ?
    O4 N4 C19 C18 . . . . -168.96(15) ?
    O3 N4 C19 C18 . . . . 9.5(2) ?
    O4 N4 C19 C20 . . . . 8.7(2) ?
    O3 N4 C19 C20 . . . . -172.85(15) ?
    C18 C19 C20 C21 . . . . 0.3(2) ?
    N4 C19 C20 C21 . . . . -177.29(15) ?
    C19 C20 C21 C16 . . . . 0.9(2) ?
    N2 C16 C21 C20 . . . . 177.43(15) ?
    C17 C16 C21 C20 . . . . -1.3(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
    N2 H2N O1 . 0.869(18) 1.979(18) 2.6254(18) 130.2(15)
