##############################################################################
###                                                                        ###
###        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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#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-03-30
_journal_date_accepted     2010-03-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      5
_journal_page_first     o1063
_journal_page_last     o1064
_journal_paper_category     QO
_journal_coeditor_code     HB5382
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '604 6579150'
_publ_contact_author_phone     '604 6533652'
_publ_section_title
;\
(4-Chlorophenyl)[1-(4-methoxyphenyl)-3-(5-nitro-2-furyl)-1H-pyrazol-4-\
yl]methanone
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Jia Hao Goh'
;
      Thomson Reuters ResearcherID: C-7576-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Nithinchandra' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
    'B. Kalluraya' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
    'N. Satheesh Rai' ?
;
      Department of Studies in Chemistry
      Mangalore University
      Mangalagangotri
      Mangalore 574 199
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(4-Chlorophenyl)[1-(4-methoxyphenyl)-3-(5-nitro-2-furyl)-1H-
pyrazol-4-yl]methanone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H14 Cl N3 O5'
_chemical_formula_sum     'C21 H14 Cl N3 O5'
_chemical_formula_iupac     'C21 H14 Cl N3 O5'
_chemical_formula_weight     423.80
_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     9.5589(8)
_cell_length_b     9.6603(8)
_cell_length_c     10.6401(9)
_cell_angle_alpha     95.523(2)
_cell_angle_beta     91.074(2)
_cell_angle_gamma     107.706(2)
_cell_volume     930.44(13)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9944
_cell_measurement_theta_min     2.63
_cell_measurement_theta_max     37.60
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'orange'
_exptl_crystal_size_max     0.35
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.513
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     436
_exptl_absorpt_coefficient_mu     0.247
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9194
_exptl_absorpt_correction_T_max     0.9632
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems
Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating
at 100.0(1)K.
;
_diffrn_ambient_temperature     100.00(10)
_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 APEX DUO CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     31674
_diffrn_reflns_av_R_equivalents     0.0255
_diffrn_reflns_av_sigmaI/netI     0.0238
_diffrn_reflns_theta_min     2.23
_diffrn_reflns_theta_max     35.00
_diffrn_reflns_theta_full     35.00
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     17
_diffrn_standards_number     0
_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     8076
_reflns_number_gt     7107
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0468
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.1166
_refine_ls_wR_factor_ref     0.1460
_refine_ls_goodness_of_fit_ref     1.129
_refine_ls_restrained_S_all     1.129
_refine_ls_number_reflns     8076
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0950P)²+0.1254P] 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     0.872
_refine_diff_density_min     -0.701
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
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
    Cl Cl1 1.29464(2) 1.14454(3) 0.06814(2) 0.02139(7) Uani d . 1 . .
    O O1 0.61940(7) 0.32154(7) 0.56102(7) 0.01521(12) Uani d . 1 . .
    O O2 0.71984(7) 0.69219(8) 0.30892(7) 0.01788(13) Uani d . 1 . .
    O O3 1.40488(8) 0.71448(9) 1.04135(7) 0.02060(14) Uani d . 1 . .
    O O4 0.30019(9) 0.02849(9) 0.52238(8) 0.02777(17) Uani d . 1 . .
    O O5 0.47299(9) 0.09317(9) 0.67232(9) 0.02794(18) Uani d . 1 . .
    N N1 0.99713(8) 0.64428(8) 0.64105(7) 0.01227(12) Uani d . 1 . .
    N N2 0.87287(8) 0.52812(8) 0.62820(7) 0.01314(12) Uani d . 1 . .
    N N3 0.41817(9) 0.10960(9) 0.57182(8) 0.01796(14) Uani d . 1 . .
    C C1 1.11008(9) 0.82550(10) 0.28130(8) 0.01484(14) Uani d . 1 . .
    H H1A 1.1386 0.7582 0.3241 0.018 Uiso calc R 1 . .
    C C2 1.21148(9) 0.92103(10) 0.21216(9) 0.01643(15) Uani d . 1 . .
    H H2A 1.3069 0.9161 0.2064 0.020 Uiso calc R 1 . .
    C C3 1.16768(9) 1.02368(10) 0.15196(8) 0.01521(14) Uani d . 1 . .
    C C4 1.02482(10) 1.03149(10) 0.15658(9) 0.01617(15) Uani d . 1 . .
    H H4A 0.9977 1.1017 0.1167 0.019 Uiso calc R 1 . .
    C C5 0.92349(9) 0.93211(10) 0.22196(8) 0.01508(14) Uani d . 1 . .
    H H5A 0.8266 0.9332 0.2228 0.018 Uiso calc R 1 . .
    C C6 0.96547(9) 0.83057(9) 0.28646(8) 0.01292(13) Uani d . 1 . .
    C C7 0.84764(9) 0.72576(9) 0.35099(8) 0.01295(13) Uani d . 1 . .
    C C8 0.88513(9) 0.66693(9) 0.46450(8) 0.01251(13) Uani d . 1 . .
    C C9 0.80310(8) 0.54115(9) 0.52175(8) 0.01230(13) Uani d . 1 . .
    C C10 0.66580(9) 0.42891(9) 0.48123(8) 0.01289(13) Uani d . 1 . .
    C C11 0.56829(10) 0.40179(10) 0.37915(8) 0.01690(15) Uani d . 1 . .
    H H11A 0.5753 0.4580 0.3119 0.020 Uiso calc R 1 . .
    C C12 0.45459(10) 0.27164(11) 0.39557(9) 0.01852(16) Uani d . 1 . .
    H H12A 0.3722 0.2250 0.3421 0.022 Uiso calc R 1 . .
    C C13 0.49222(9) 0.23009(9) 0.50622(9) 0.01568(15) Uani d . 1 . .
    C C14 1.00849(9) 0.72922(9) 0.54574(8) 0.01321(14) Uani d . 1 . .
    H H14A 1.0848 0.8137 0.5363 0.016 Uiso calc R 1 . .
    C C15 1.09929(9) 0.66115(9) 0.74528(8) 0.01229(13) Uani d . 1 . .
    C C16 1.07607(9) 0.55323(10) 0.82671(8) 0.01586(15) Uani d . 1 . .
    H H16A 0.9930 0.4716 0.8143 0.019 Uiso calc R 1 . .
    C C17 1.17703(10) 0.56696(11) 0.92700(9) 0.01755(15) Uani d . 1 . .
    H H17A 1.1624 0.4936 0.9805 0.021 Uiso calc R 1 . .
    C C18 1.29982(9) 0.69077(10) 0.94696(8) 0.01540(14) Uani d . 1 . .
    C C19 1.32113(9) 0.80016(10) 0.86573(9) 0.01607(15) Uani d . 1 . .
    H H19A 1.4019 0.8839 0.8800 0.019 Uiso calc R 1 . .
    C C20 1.22302(9) 0.78476(9) 0.76433(8) 0.01446(14) Uani d . 1 . .
    H H20A 1.2393 0.8564 0.7091 0.017 Uiso calc R 1 . .
    C C21 1.39244(12) 0.60104(13) 1.12158(10) 0.0247(2) Uani d . 1 . .
    H H21A 1.4770 0.6276 1.1793 0.037 Uiso calc R 1 . .
    H H21B 1.3867 0.5115 1.0709 0.037 Uiso calc R 1 . .
    H H21C 1.3053 0.5879 1.1684 0.037 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
    Cl1 C3 . 1.7351(9) ?
    O1 C13 . 1.3488(11) ?
    O1 C10 . 1.3774(10) ?
    O2 C7 . 1.2282(10) ?
    O3 C18 . 1.3593(11) ?
    O3 C21 . 1.4313(13) ?
    O4 N3 . 1.2343(11) ?
    O5 N3 . 1.2270(12) ?
    N1 C14 . 1.3503(11) ?
    N1 N2 . 1.3574(10) ?
    N1 C15 . 1.4275(11) ?
    N2 C9 . 1.3393(11) ?
    N3 C13 . 1.4200(12) ?
    C1 C2 . 1.3949(12) ?
    C1 C6 . 1.3998(12) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.3906(12) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.3919(12) ?
    C4 C5 . 1.3899(13) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.3975(12) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.4948(12) ?
    C7 C8 . 1.4662(12) ?
    C8 C14 . 1.3892(11) ?
    C8 C9 . 1.4294(11) ?
    C9 C10 . 1.4516(11) ?
    C10 C11 . 1.3696(12) ?
    C11 C12 . 1.4180(13) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.3563(13) ?
    C12 H12A . 0.9300 ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.3883(12) ?
    C15 C20 . 1.3969(12) ?
    C16 C17 . 1.3942(12) ?
    C16 H16A . 0.9300 ?
    C17 C18 . 1.3933(13) ?
    C17 H17A . 0.9300 ?
    C18 C19 . 1.3987(13) ?
    C19 C20 . 1.3828(12) ?
    C19 H19A . 0.9300 ?
    C20 H20A . 0.9300 ?
    C21 H21A . 0.9600 ?
    C21 H21B . 0.9600 ?
    C21 H21C . 0.9600 ?
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
    C13 O1 C10 . . 105.18(7) ?
    C18 O3 C21 . . 117.66(8) ?
    C14 N1 N2 . . 112.41(7) ?
    C14 N1 C15 . . 128.09(7) ?
    N2 N1 C15 . . 119.46(7) ?
    C9 N2 N1 . . 105.18(7) ?
    O5 N3 O4 . . 124.52(9) ?
    O5 N3 C13 . . 119.17(8) ?
    O4 N3 C13 . . 116.31(9) ?
    C2 C1 C6 . . 120.23(8) ?
    C2 C1 H1A . . 119.9 ?
    C6 C1 H1A . . 119.9 ?
    C3 C2 C1 . . 118.94(8) ?
    C3 C2 H2A . . 120.5 ?
    C1 C2 H2A . . 120.5 ?
    C2 C3 C4 . . 121.82(8) ?
    C2 C3 Cl1 . . 118.96(7) ?
    C4 C3 Cl1 . . 119.22(7) ?
    C5 C4 C3 . . 118.60(8) ?
    C5 C4 H4A . . 120.7 ?
    C3 C4 H4A . . 120.7 ?
    C4 C5 C6 . . 120.81(8) ?
    C4 C5 H5A . . 119.6 ?
    C6 C5 H5A . . 119.6 ?
    C5 C6 C1 . . 119.53(8) ?
    C5 C6 C7 . . 116.77(7) ?
    C1 C6 C7 . . 123.58(7) ?
    O2 C7 C8 . . 120.95(8) ?
    O2 C7 C6 . . 119.13(8) ?
    C8 C7 C6 . . 119.91(7) ?
    C14 C8 C9 . . 104.13(7) ?
    C14 C8 C7 . . 126.36(8) ?
    C9 C8 C7 . . 129.40(7) ?
    N2 C9 C8 . . 110.98(7) ?
    N2 C9 C10 . . 117.95(7) ?
    C8 C9 C10 . . 131.03(8) ?
    C11 C10 O1 . . 110.07(7) ?
    C11 C10 C9 . . 134.98(8) ?
    O1 C10 C9 . . 114.95(7) ?
    C10 C11 C12 . . 106.87(8) ?
    C10 C11 H11A . . 126.6 ?
    C12 C11 H11A . . 126.6 ?
    C13 C12 C11 . . 104.95(8) ?
    C13 C12 H12A . . 127.5 ?
    C11 C12 H12A . . 127.5 ?
    O1 C13 C12 . . 112.92(8) ?
    O1 C13 N3 . . 116.80(8) ?
    C12 C13 N3 . . 130.27(8) ?
    N1 C14 C8 . . 107.30(7) ?
    N1 C14 H14A . . 126.3 ?
    C8 C14 H14A . . 126.3 ?
    C16 C15 C20 . . 120.14(8) ?
    C16 C15 N1 . . 119.68(7) ?
    C20 C15 N1 . . 120.17(7) ?
    C15 C16 C17 . . 120.14(8) ?
    C15 C16 H16A . . 119.9 ?
    C17 C16 H16A . . 119.9 ?
    C18 C17 C16 . . 119.84(8) ?
    C18 C17 H17A . . 120.1 ?
    C16 C17 H17A . . 120.1 ?
    O3 C18 C17 . . 124.49(8) ?
    O3 C18 C19 . . 115.85(8) ?
    C17 C18 C19 . . 119.66(8) ?
    C20 C19 C18 . . 120.48(8) ?
    C20 C19 H19A . . 119.8 ?
    C18 C19 H19A . . 119.8 ?
    C19 C20 C15 . . 119.70(8) ?
    C19 C20 H20A . . 120.1 ?
    C15 C20 H20A . . 120.1 ?
    O3 C21 H21A . . 109.5 ?
    O3 C21 H21B . . 109.5 ?
    H21A C21 H21B . . 109.5 ?
    O3 C21 H21C . . 109.5 ?
    H21A C21 H21C . . 109.5 ?
    H21B C21 H21C . . 109.5 ?
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
    C14 N1 N2 C9 . . . . -0.53(9) ?
    C15 N1 N2 C9 . . . . -178.56(7) ?
    C6 C1 C2 C3 . . . . 1.91(13) ?
    C1 C2 C3 C4 . . . . -1.44(14) ?
    C1 C2 C3 Cl1 . . . . 178.93(7) ?
    C2 C3 C4 C5 . . . . -0.89(14) ?
    Cl1 C3 C4 C5 . . . . 178.74(7) ?
    C3 C4 C5 C6 . . . . 2.78(14) ?
    C4 C5 C6 C1 . . . . -2.31(13) ?
    C4 C5 C6 C7 . . . . -178.41(8) ?
    C2 C1 C6 C5 . . . . -0.08(13) ?
    C2 C1 C6 C7 . . . . 175.74(8) ?
    C5 C6 C7 O2 . . . . 27.96(12) ?
    C1 C6 C7 O2 . . . . -147.96(9) ?
    C5 C6 C7 C8 . . . . -150.78(8) ?
    C1 C6 C7 C8 . . . . 33.30(12) ?
    O2 C7 C8 C14 . . . . -156.41(9) ?
    C6 C7 C8 C14 . . . . 22.30(12) ?
    O2 C7 C8 C9 . . . . 19.38(14) ?
    C6 C7 C8 C9 . . . . -161.90(8) ?
    N1 N2 C9 C8 . . . . 0.76(9) ?
    N1 N2 C9 C10 . . . . 178.64(7) ?
    C14 C8 C9 N2 . . . . -0.72(9) ?
    C7 C8 C9 N2 . . . . -177.23(8) ?
    C14 C8 C9 C10 . . . . -178.24(8) ?
    C7 C8 C9 C10 . . . . 5.26(15) ?
    C13 O1 C10 C11 . . . . -0.45(9) ?
    C13 O1 C10 C9 . . . . -179.91(7) ?
    N2 C9 C10 C11 . . . . -177.28(9) ?
    C8 C9 C10 C11 . . . . 0.10(16) ?
    N2 C9 C10 O1 . . . . 2.01(11) ?
    C8 C9 C10 O1 . . . . 179.38(8) ?
    O1 C10 C11 C12 . . . . 0.31(10) ?
    C9 C10 C11 C12 . . . . 179.62(9) ?
    C10 C11 C12 C13 . . . . -0.05(10) ?
    C10 O1 C13 C12 . . . . 0.43(10) ?
    C10 O1 C13 N3 . . . . -178.49(7) ?
    C11 C12 C13 O1 . . . . -0.24(11) ?
    C11 C12 C13 N3 . . . . 178.50(9) ?
    O5 N3 C13 O1 . . . . -1.02(13) ?
    O4 N3 C13 O1 . . . . 178.36(8) ?
    O5 N3 C13 C12 . . . . -179.72(10) ?
    O4 N3 C13 C12 . . . . -0.34(15) ?
    N2 N1 C14 C8 . . . . 0.08(9) ?
    C15 N1 C14 C8 . . . . 177.90(7) ?
    C9 C8 C14 N1 . . . . 0.37(9) ?
    C7 C8 C14 N1 . . . . 177.02(8) ?
    C14 N1 C15 C16 . . . . -172.85(8) ?
    N2 N1 C15 C16 . . . . 4.84(12) ?
    C14 N1 C15 C20 . . . . 6.33(13) ?
    N2 N1 C15 C20 . . . . -175.98(7) ?
    C20 C15 C16 C17 . . . . -0.74(13) ?
    N1 C15 C16 C17 . . . . 178.45(8) ?
    C15 C16 C17 C18 . . . . 1.34(14) ?
    C21 O3 C18 C17 . . . . 3.45(14) ?
    C21 O3 C18 C19 . . . . -176.00(9) ?
    C16 C17 C18 O3 . . . . -179.70(8) ?
    C16 C17 C18 C19 . . . . -0.27(14) ?
    O3 C18 C19 C20 . . . . 178.05(8) ?
    C17 C18 C19 C20 . . . . -1.43(13) ?
    C18 C19 C20 C15 . . . . 2.03(13) ?
    C16 C15 C20 C19 . . . . -0.95(13) ?
    N1 C15 C20 C19 . . . . 179.87(8) ?
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
    C11 H11A O2 . 0.93 2.27 2.9153(12) 126 yes
    C2 H2A O5 2_766 0.93 2.48 3.2820(13) 145 yes
    C14 H14A O4 1_665 0.93 2.46 3.3846(12) 175 yes
    C21 H21A O2 1_656 0.96 2.55 3.5064(14) 173 yes
