##############################################################################
#                                                                            #
# 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 Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2011-11-22
_journal_date_accepted     2011-11-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2011
_journal_volume     67
_journal_issue     12
_journal_page_first     o3471
_journal_page_last     o3472
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536811050239
_journal_coeditor_code     HB6529
_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
;\
N'-[(E)-(3-Phenyl-1H-pyrazol-4-yl)methylidene]naphtho[2,1-\
b]furan-2-carbohydrazide monohydrate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Hoong-Kun Fun'
;
      Thomson Reuters ResearcherID: A-3561-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Wan-Sin Loh'
;
      Thomson Reuters ResearcherID: C-7581-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Shridhar Malladi' ?
;
      Medicinal Chemistry Division
      Department of Chemistry
      National Institute of Technology-Karnataka
      Surathkal, Mangalore 575 025
      India
;
    'Ganesh, B. M.' ?
;
      Medicinal Chemistry Division
      Department of Chemistry
      National Institute of Technology-Karnataka
      Surathkal, Mangalore 575 025
      India
;
    'Arun M. Isloor' ?
;
      Medicinal Chemistry Division
      Department of Chemistry
      National Institute of Technology-Karnataka
      Surathkal, Mangalore 575 025
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-[(E)-(3-Phenyl-1H-pyrazol-4-
yl)methylidene]naphtho[2,1-b]furan-2-carbohydrazide monohydrate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H16 N4 O2, H2 O'
_chemical_formula_sum     'C23 H18 N4 O3'
_chemical_formula_iupac     'C23 H16 N4 O2, H2 O'
_chemical_formula_weight     398.41
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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     7.13830(10)
_cell_length_b     9.39280(10)
_cell_length_c     28.4200(4)
_cell_angle_alpha     90.00
_cell_angle_beta     96.8640(10)
_cell_angle_gamma     90.00
_cell_volume     1891.86(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3650
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     29.52
_cell_measurement_temperature     100.0(10)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.399
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     832
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.9711
_exptl_absorpt_correction_T_max     0.9829
_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 APEXII CCD'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     21248
_diffrn_reflns_av_R_equivalents     0.0578
_diffrn_reflns_av_sigmaI/netI     0.0544
_diffrn_reflns_theta_min     1.44
_diffrn_reflns_theta_max     30.06
_diffrn_reflns_theta_full     30.06
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     13
_diffrn_reflns_limit_l_min     -39
_diffrn_reflns_limit_l_max     40
_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 >
σ(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     5516
_reflns_number_gt     3857
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0829
_refine_ls_R_factor_gt     0.0513
_refine_ls_wR_factor_gt     0.1127
_refine_ls_wR_factor_ref     0.1287
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     5516
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0566P)²+0.4389P] 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     0.271
_refine_diff_density_min     -0.270
_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     '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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.43329(14) 1.04167(12) 0.06904(4) 0.0190(2) Uani d . 1 1 . .
    O O2 0.91817(15) 1.01592(13) 0.11647(4) 0.0251(3) Uani d . 1 1 . .
    N N1 0.65264(19) 0.90451(14) 0.13601(4) 0.0177(3) Uani d . 1 1 . .
    N N2 0.75457(18) 0.82808(14) 0.17263(4) 0.0177(3) Uani d . 1 1 . .
    N N3 0.93853(18) 0.49668(15) 0.27204(5) 0.0196(3) Uani d . 1 1 . .
    N N4 0.78932(17) 0.40748(14) 0.26062(5) 0.0196(3) Uani d . 1 1 . .
    C C1 0.3524(2) 1.12767(17) 0.03335(5) 0.0183(3) Uani d . 1 1 . .
    C C2 0.1589(2) 1.13360(19) 0.01844(6) 0.0232(3) Uani d . 1 1 . .
    H H2A 0.0711 1.0769 0.0327 0.028 Uiso calc R 1 1 . .
    C C3 0.1027(2) 1.22541(19) -0.01779(6) 0.0245(4) Uani d . 1 1 . .
    H H3A -0.0275 1.2308 -0.0294 0.029 Uiso calc R 1 1 . .
    C C4 0.2337(2) 1.31378(18) -0.03878(6) 0.0212(3) Uani d . 1 1 . .
    C C5 0.1705(2) 1.41189(19) -0.07502(6) 0.0242(4) Uani d . 1 1 . .
    H H5A 0.0398 1.4178 -0.0861 0.029 Uiso calc R 1 1 . .
    C C6 0.2963(2) 1.49881(18) -0.09438(6) 0.0248(4) Uani d . 1 1 . .
    H H6A 0.2514 1.5661 -0.1180 0.030 Uiso calc R 1 1 . .
    C C7 0.4909(2) 1.48864(18) -0.07936(6) 0.0238(3) Uani d . 1 1 . .
    H H7A 0.5772 1.5474 -0.0934 0.029 Uiso calc R 1 1 . .
    C C8 0.5563(2) 1.39364(17) -0.04433(6) 0.0210(3) Uani d . 1 1 . .
    H H8A 0.6878 1.3874 -0.0343 0.025 Uiso calc R 1 1 . .
    C C9 0.4303(2) 1.30561(17) -0.02320(5) 0.0185(3) Uani d . 1 1 . .
    C C10 0.4875(2) 1.20827(16) 0.01465(5) 0.0170(3) Uani d . 1 1 . .
    C C11 0.6639(2) 1.17157(17) 0.04153(5) 0.0188(3) Uani d . 1 1 . .
    H H11A 0.7846 1.2095 0.0377 0.023 Uiso calc R 1 1 . .
    C C12 0.6241(2) 1.07205(17) 0.07342(5) 0.0175(3) Uani d . 1 1 . .
    C C13 0.7456(2) 0.99555(17) 0.11028(5) 0.0184(3) Uani d . 1 1 . .
    C C14 0.6704(2) 0.71368(16) 0.18341(5) 0.0167(3) Uani d . 1 1 . .
    H H14A 0.5497 0.6931 0.1669 0.020 Uiso calc R 1 1 . .
    C C15 0.7500(2) 0.61507(16) 0.21930(5) 0.0166(3) Uani d . 1 1 . .
    C C16 0.9210(2) 0.61994(17) 0.24849(5) 0.0185(3) Uani d . 1 1 . .
    H H16A 1.0087 0.6965 0.2512 0.022 Uiso calc R 1 1 . .
    C C17 0.6738(2) 0.47933(16) 0.22852(5) 0.0168(3) Uani d . 1 1 . .
    C C18 0.4979(2) 0.41425(16) 0.20556(5) 0.0169(3) Uani d . 1 1 . .
    C C19 0.4996(2) 0.27495(17) 0.18791(5) 0.0197(3) Uani d . 1 1 . .
    H H19A 0.6122 0.2203 0.1927 0.024 Uiso calc R 1 1 . .
    C C20 0.3376(2) 0.21643(18) 0.16353(6) 0.0229(3) Uani d . 1 1 . .
    H H20A 0.3396 0.1219 0.1517 0.027 Uiso calc R 1 1 . .
    C C21 0.1728(2) 0.29580(19) 0.15644(6) 0.0236(4) Uani d . 1 1 . .
    H H21A 0.0629 0.2564 0.1391 0.028 Uiso calc R 1 1 . .
    C C22 0.1685(2) 0.43245(18) 0.17454(5) 0.0209(3) Uani d . 1 1 . .
    H H22A 0.0550 0.4862 0.1700 0.025 Uiso calc R 1 1 . .
    C C23 0.3301(2) 0.49127(17) 0.19929(5) 0.0187(3) Uani d . 1 1 . .
    H H23A 0.3259 0.5846 0.2120 0.022 Uiso calc R 1 1 . .
    O O1W 0.25339(16) 0.83476(13) 0.13979(4) 0.0270(3) Uani d . 1 1 . .
    H H1W1 0.2518 0.8380 0.1701 0.041 Uiso d R 1 1 . .
    H H2W1 0.1460 0.8694 0.1251 0.041 Uiso d R 1 1 . .
    H H1N3 1.036(3) 0.467(3) 0.2959(9) 0.064(8) Uiso d . 1 1 . .
    H H1N1 0.523(4) 0.888(3) 0.1276(9) 0.061(7) Uiso d . 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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 . 1.3692(18) ?
    O1 C12 . 1.3826(17) ?
    O2 C13 . 1.2383(18) ?
    N1 C13 . 1.3499(19) ?
    N1 N2 . 1.3954(17) ?
    N1 H1N1 . 0.94(2) ?
    N2 C14 . 1.2860(19) ?
    N3 C16 . 1.336(2) ?
    N3 N4 . 1.3636(18) ?
    N3 H1N3 . 0.96(2) ?
    N4 C17 . 1.3372(19) ?
    C1 C10 . 1.381(2) ?
    C1 C2 . 1.397(2) ?
    C2 C3 . 1.366(2) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.433(2) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.415(2) ?
    C4 C9 . 1.422(2) ?
    C5 C6 . 1.376(2) ?
    C5 H5A . 0.9500 ?
    C6 C7 . 1.407(2) ?
    C6 H6A . 0.9500 ?
    C7 C8 . 1.376(2) ?
    C7 H7A . 0.9500 ?
    C8 C9 . 1.408(2) ?
    C8 H8A . 0.9500 ?
    C9 C10 . 1.433(2) ?
    C10 C11 . 1.435(2) ?
    C11 C12 . 1.356(2) ?
    C11 H11A . 0.9500 ?
    C12 C13 . 1.466(2) ?
    C14 C15 . 1.443(2) ?
    C14 H14A . 0.9500 ?
    C15 C16 . 1.392(2) ?
    C15 C17 . 1.423(2) ?
    C16 H16A . 0.9500 ?
    C17 C18 . 1.476(2) ?
    C18 C23 . 1.393(2) ?
    C18 C19 . 1.402(2) ?
    C19 C20 . 1.389(2) ?
    C19 H19A . 0.9500 ?
    C20 C21 . 1.387(2) ?
    C20 H20A . 0.9500 ?
    C21 C22 . 1.384(2) ?
    C21 H21A . 0.9500 ?
    C22 C23 . 1.392(2) ?
    C22 H22A . 0.9500 ?
    C23 H23A . 0.9500 ?
    O1W H1W1 . 0.8628 ?
    O1W H2W1 . 0.8895 ?
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 C12 . . 105.57(12) ?
    C13 N1 N2 . . 118.93(13) ?
    C13 N1 H1N1 . . 119.8(15) ?
    N2 N1 H1N1 . . 121.1(15) ?
    C14 N2 N1 . . 113.00(12) ?
    C16 N3 N4 . . 112.94(13) ?
    C16 N3 H1N3 . . 128.8(15) ?
    N4 N3 H1N3 . . 118.2(15) ?
    C17 N4 N3 . . 104.65(13) ?
    O1 C1 C10 . . 110.89(13) ?
    O1 C1 C2 . . 124.22(14) ?
    C10 C1 C2 . . 124.89(14) ?
    C3 C2 C1 . . 116.37(15) ?
    C3 C2 H2A . . 121.8 ?
    C1 C2 H2A . . 121.8 ?
    C2 C3 C4 . . 122.18(15) ?
    C2 C3 H3A . . 118.9 ?
    C4 C3 H3A . . 118.9 ?
    C5 C4 C9 . . 118.60(15) ?
    C5 C4 C3 . . 120.88(15) ?
    C9 C4 C3 . . 120.51(14) ?
    C6 C5 C4 . . 120.73(15) ?
    C6 C5 H5A . . 119.6 ?
    C4 C5 H5A . . 119.6 ?
    C5 C6 C7 . . 120.41(15) ?
    C5 C6 H6A . . 119.8 ?
    C7 C6 H6A . . 119.8 ?
    C8 C7 C6 . . 120.04(15) ?
    C8 C7 H7A . . 120.0 ?
    C6 C7 H7A . . 120.0 ?
    C7 C8 C9 . . 120.71(15) ?
    C7 C8 H8A . . 119.6 ?
    C9 C8 H8A . . 119.6 ?
    C8 C9 C4 . . 119.48(14) ?
    C8 C9 C10 . . 123.75(14) ?
    C4 C9 C10 . . 116.75(14) ?
    C1 C10 C9 . . 119.27(14) ?
    C1 C10 C11 . . 105.79(13) ?
    C9 C10 C11 . . 134.91(14) ?
    C12 C11 C10 . . 106.30(13) ?
    C12 C11 H11A . . 126.8 ?
    C10 C11 H11A . . 126.8 ?
    C11 C12 O1 . . 111.43(13) ?
    C11 C12 C13 . . 131.48(14) ?
    O1 C12 C13 . . 117.09(13) ?
    O2 C13 N1 . . 124.46(14) ?
    O2 C13 C12 . . 121.30(14) ?
    N1 C13 C12 . . 114.24(13) ?
    N2 C14 C15 . . 123.27(14) ?
    N2 C14 H14A . . 118.4 ?
    C15 C14 H14A . . 118.4 ?
    C16 C15 C17 . . 104.31(13) ?
    C16 C15 C14 . . 130.05(14) ?
    C17 C15 C14 . . 125.31(14) ?
    N3 C16 C15 . . 107.04(14) ?
    N3 C16 H16A . . 126.5 ?
    C15 C16 H16A . . 126.5 ?
    N4 C17 C15 . . 111.07(13) ?
    N4 C17 C18 . . 121.01(14) ?
    C15 C17 C18 . . 127.84(13) ?
    C23 C18 C19 . . 118.89(14) ?
    C23 C18 C17 . . 120.96(14) ?
    C19 C18 C17 . . 120.10(14) ?
    C20 C19 C18 . . 120.38(15) ?
    C20 C19 H19A . . 119.8 ?
    C18 C19 H19A . . 119.8 ?
    C21 C20 C19 . . 120.06(15) ?
    C21 C20 H20A . . 120.0 ?
    C19 C20 H20A . . 120.0 ?
    C22 C21 C20 . . 120.04(15) ?
    C22 C21 H21A . . 120.0 ?
    C20 C21 H21A . . 120.0 ?
    C21 C22 C23 . . 120.13(15) ?
    C21 C22 H22A . . 119.9 ?
    C23 C22 H22A . . 119.9 ?
    C22 C23 C18 . . 120.45(15) ?
    C22 C23 H23A . . 119.8 ?
    C18 C23 H23A . . 119.8 ?
    H1W1 O1W H2W1 . . 110.0 ?
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
    C13 N1 N2 C14 . . . . -157.33(14) ?
    C16 N3 N4 C17 . . . . -0.15(17) ?
    C12 O1 C1 C10 . . . . 1.37(17) ?
    C12 O1 C1 C2 . . . . -177.96(15) ?
    O1 C1 C2 C3 . . . . -179.88(15) ?
    C10 C1 C2 C3 . . . . 0.9(3) ?
    C1 C2 C3 C4 . . . . -1.5(3) ?
    C2 C3 C4 C5 . . . . -177.51(16) ?
    C2 C3 C4 C9 . . . . 1.8(3) ?
    C9 C4 C5 C6 . . . . -0.8(2) ?
    C3 C4 C5 C6 . . . . 178.56(16) ?
    C4 C5 C6 C7 . . . . 1.8(3) ?
    C5 C6 C7 C8 . . . . -1.5(3) ?
    C6 C7 C8 C9 . . . . 0.1(2) ?
    C7 C8 C9 C4 . . . . 0.9(2) ?
    C7 C8 C9 C10 . . . . -177.53(15) ?
    C5 C4 C9 C8 . . . . -0.6(2) ?
    C3 C4 C9 C8 . . . . -179.93(15) ?
    C5 C4 C9 C10 . . . . 177.97(14) ?
    C3 C4 C9 C10 . . . . -1.4(2) ?
    O1 C1 C10 C9 . . . . -179.87(13) ?
    C2 C1 C10 C9 . . . . -0.5(2) ?
    O1 C1 C10 C11 . . . . -1.39(17) ?
    C2 C1 C10 C11 . . . . 177.93(15) ?
    C8 C9 C10 C1 . . . . 179.24(15) ?
    C4 C9 C10 C1 . . . . 0.8(2) ?
    C8 C9 C10 C11 . . . . 1.3(3) ?
    C4 C9 C10 C11 . . . . -177.16(16) ?
    C1 C10 C11 C12 . . . . 0.84(17) ?
    C9 C10 C11 C12 . . . . 178.97(17) ?
    C10 C11 C12 O1 . . . . -0.02(18) ?
    C10 C11 C12 C13 . . . . -179.69(16) ?
    C1 O1 C12 C11 . . . . -0.81(17) ?
    C1 O1 C12 C13 . . . . 178.90(13) ?
    N2 N1 C13 O2 . . . . 0.8(2) ?
    N2 N1 C13 C12 . . . . -178.86(13) ?
    C11 C12 C13 O2 . . . . -0.6(3) ?
    O1 C12 C13 O2 . . . . 179.70(14) ?
    C11 C12 C13 N1 . . . . 178.97(16) ?
    O1 C12 C13 N1 . . . . -0.7(2) ?
    N1 N2 C14 C15 . . . . 178.31(13) ?
    N2 C14 C15 C16 . . . . 0.5(3) ?
    N2 C14 C15 C17 . . . . -171.90(14) ?
    N4 N3 C16 C15 . . . . 0.06(17) ?
    C17 C15 C16 N3 . . . . 0.06(16) ?
    C14 C15 C16 N3 . . . . -173.53(15) ?
    N3 N4 C17 C15 . . . . 0.18(16) ?
    N3 N4 C17 C18 . . . . 177.03(13) ?
    C16 C15 C17 N4 . . . . -0.15(17) ?
    C14 C15 C17 N4 . . . . 173.83(14) ?
    C16 C15 C17 C18 . . . . -176.73(14) ?
    C14 C15 C17 C18 . . . . -2.8(2) ?
    N4 C17 C18 C23 . . . . 136.78(15) ?
    C15 C17 C18 C23 . . . . -46.9(2) ?
    N4 C17 C18 C19 . . . . -45.9(2) ?
    C15 C17 C18 C19 . . . . 130.41(16) ?
    C23 C18 C19 C20 . . . . 1.6(2) ?
    C17 C18 C19 C20 . . . . -175.76(14) ?
    C18 C19 C20 C21 . . . . 0.1(2) ?
    C19 C20 C21 C22 . . . . -1.4(2) ?
    C20 C21 C22 C23 . . . . 0.9(2) ?
    C21 C22 C23 C18 . . . . 0.8(2) ?
    C19 C18 C23 C22 . . . . -2.1(2) ?
    C17 C18 C23 C22 . . . . 175.28(14) ?
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
    O1W H1W1 N4 2_655 0.86 2.13 2.9625(18) 163 yes
    O1W H2W1 O2 1_455 0.89 2.12 2.9465(16) 154 yes
    N3 H1N3 O2 2_745 0.95(2) 2.52(3) 3.2162(18) 130.4(19) yes
    N3 H1N3 N2 2_745 0.95(2) 2.10(3) 2.9927(19) 155(2) yes
    N1 H1N1 O1W . 0.94(3) 2.06(3) 2.9388(18) 155(2) yes
    C14 H14A O1W . 0.95 2.54 3.2877(18) 136 yes
    C16 H16A N4 2_755 0.95 2.50 3.430(2) 167 yes
    C21 H21A O2 1_445 0.95 2.53 3.318(2) 140 yes
    C7 H7A Cg2 3_675 0.95 2.80 3.6022(18) 142 yes
    C22 H22A Cg1 1_455 0.95 2.93 3.5274(16) 122 yes
