##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
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data_I
_audit_creation_method     'SHELXL-2014/7'
_journal_date_recd_electronic     2016-06-11
_journal_date_accepted     2016-06-14
_journal_name_full     'IUCrData'
_journal_year     2016
_journal_volume     1
_journal_issue      6
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314616009615
_journal_coeditor_code     SJ4047
_publ_contact_author_name     'Mohammed Naas'
_publ_contact_author_address
;
Laboratoire de Chimie Organique Appliquée-  Chimie Appliquée,
Faculté des Sciences et Techniques,
Université Sidi Mohamed Ben Abdallah, Fès, Morocco
;
_publ_contact_author_email     'naas_m21@yahoo.com'
_publ_contact_author_fax     '212 537 77 54 40'
_publ_contact_author_phone     '212 537 77 54 40'
_publ_section_title
;
1-Methyl-5-nitro-3-phenyl-1H-indazole
;
loop_
    _publ_author_name
    _publ_author_address
    'Naas, Mohammed'
;
Laboratoire de Chimie Organique Heterocyclique URAC 21,
Pôle de Compétences Pharmacochimie Faculté des Sciences,
Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat,
Morocco
Institut de Chimie Organique et Analytique (ICOA), Université d'Orleans
UMR CNRS 7311, BP 6759, 45067 Orléans Cedex 2, France
;
    'Benchidmi, Mohammed'
;
Laboratoire de Chimie Organique Heterocyclique URAC 21,
Pôle de Compétences Pharmacochimie Faculté des Sciences,
Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat,
Morocco
;
    'Essassi, El Mokhtar'
;
Laboratoire de Chimie Organique Heterocyclique URAC 21,
Pôle de Compétences Pharmacochimie Faculté des Sciences,
Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat,
Morocco
;
    'Saadi, Mohamed'
;
Laboratoire de Chimie du Solide Appliquée,
Faculty of Sciences, Mohammed V University in Rabat
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
    'El Ammari, Lahcen'
;
Laboratoire de Chimie du Solide Appliquée,
Faculty of Sciences, Mohammed V University in Rabat
Avenue Ibn Battouta, BP 1014, Rabat, Morocco
;
_publ_section_synopsis
;
The indazole ring system and the nitro groups are nearly coplanar. The crystal
structure is stabilized by hydrogen bonds and π--π stacking interactions.
;
_database_code_depnum_ccdc_archive     'CCDC 1485400'
_chemical_name_systematic
;
1-Methyl-5-nitro-3-phenyl-1H-indazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 N3 O2'
_chemical_formula_sum     'C14 H11 N3 O2'
_chemical_formula_iupac     'C14 H11 N3 O2'
_chemical_formula_weight     253.26
_chemical_melting_point     396
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P c a 21'
_space_group_name_Hall     'P 2c -2ac'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y, z'
    '-x+1/2, y, z+1/2'
_cell_length_a     33.4769(17)
_cell_length_b     7.4977(3)
_cell_length_c     9.7916(4)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2457.69(19)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5245
_cell_measurement_theta_min     2.410
_cell_measurement_theta_max     27.101
_cell_measurement_temperature     296(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.330
_exptl_crystal_size_mid     0.280
_exptl_crystal_size_min     0.190
_exptl_crystal_density_diffrn     1.369
_exptl_crystal_F_000     1056
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_exptl_absorpt_correction_T_min     0.6379
_exptl_absorpt_correction_T_max     0.7464
_diffrn_ambient_temperature     296(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 X8 APEX'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_reflns_number     13395
_diffrn_reflns_av_R_equivalents     0.0396
_diffrn_reflns_theta_min     2.410
_diffrn_reflns_theta_max     27.101
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -30
_diffrn_reflns_limit_h_max     42
_diffrn_reflns_limit_k_min     -9
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_reflns_number_total     5245
_reflns_number_gt     3328
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0906
_refine_ls_R_factor_gt     0.0490
_refine_ls_wR_factor_gt     0.1101
_refine_ls_wR_factor_ref     0.1300
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.010
_refine_ls_number_reflns     5245
_refine_ls_number_parameters     344
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0579P)²+0.0910P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.159
_refine_diff_density_min     -0.151
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     2(2)
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-Plus (Bruker, 2009)
;
_computing_data_reduction
;
SAINT-Plus (Bruker, 2009)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia,
2012) and Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
PLATON (Spek, 2009) and publCIF (Westrip, 2010)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.45757(13) 0.7758(5) 0.8046(5) 0.0631(11) Uani d 1 . .
    H H1 0.4420 0.7154 0.7410 0.076 Uiso calc 1 . .
    C C2 0.49860(16) 0.7540(6) 0.8036(6) 0.0797(14) Uani d 1 . .
    H H2 0.5105 0.6813 0.7382 0.096 Uiso calc 1 . .
    C C3 0.52212(14) 0.8402(7) 0.8998(6) 0.0784(14) Uani d 1 . .
    H H3 0.5497 0.8247 0.8998 0.094 Uiso calc 1 . .
    C C4 0.50432(14) 0.9486(6) 0.9949(5) 0.0708(13) Uani d 1 . .
    H H4 0.5200 1.0059 1.0599 0.085 Uiso calc 1 . .
    C C5 0.46349(12) 0.9737(5) 0.9955(4) 0.0579(10) Uani d 1 . .
    H H5 0.4519 1.0488 1.0600 0.069 Uiso calc 1 . .
    C C6 0.43943(12) 0.8867(5) 0.8996(4) 0.0488(9) Uani d 1 . .
    C C7 0.39618(12) 0.9148(5) 0.8928(4) 0.0477(9) Uani d 1 . .
    C C8 0.36860(11) 0.9732(4) 0.9954(4) 0.0461(9) Uani d 1 . .
    C C9 0.37031(13) 1.0185(4) 1.1343(4) 0.0494(9) Uani d 1 . .
    H H9 0.3942 1.0138 1.1827 0.059 Uiso calc 1 . .
    C C10 0.33550(14) 1.0697(5) 1.1956(4) 0.0544(10) Uani d 1 . .
    C C11 0.29892(13) 1.0770(6) 1.1283(5) 0.0622(11) Uani d 1 . .
    H H11 0.2762 1.1139 1.1751 0.075 Uiso calc 1 . .
    C C12 0.29627(13) 1.0300(5) 0.9938(5) 0.0615(11) Uani d 1 . .
    H H12 0.2720 1.0332 0.9473 0.074 Uiso calc 1 . .
    C C13 0.33147(11) 0.9771(5) 0.9290(4) 0.0496(9) Uani d 1 . .
    C C14 0.30967(14) 0.9067(6) 0.6881(4) 0.0697(13) Uani d 1 . .
    H H14A 0.2835 0.9377 0.7204 0.105 Uiso calc 1 . .
    H H14B 0.3172 0.9860 0.6155 0.105 Uiso calc 1 . .
    H H14C 0.3095 0.7862 0.6548 0.105 Uiso calc 1 . .
    C C15 0.06659(14) 0.6121(5) 0.7116(5) 0.0586(11) Uani d 1 . .
    H H15 0.0443 0.6102 0.6551 0.070 Uiso calc 1 . .
    C C16 0.06358(16) 0.6833(7) 0.8421(6) 0.0804(14) Uani d 1 . .
    H H16 0.0393 0.7283 0.8727 0.096 Uiso calc 1 . .
    C C17 0.09621(17) 0.6875(7) 0.9256(5) 0.0807(14) Uani d 1 . .
    H H17 0.0941 0.7362 1.0127 0.097 Uiso calc 1 . .
    C C18 0.13218(16) 0.6199(6) 0.8814(4) 0.0709(13) Uani d 1 . .
    H H18 0.1544 0.6233 0.9384 0.085 Uiso calc 1 . .
    C C19 0.13518(14) 0.5474(6) 0.7527(4) 0.0582(11) Uani d 1 . .
    H H19 0.1594 0.5001 0.7240 0.070 Uiso calc 1 . .
    C C20 0.10261(12) 0.5436(5) 0.6649(4) 0.0456(9) Uani d 1 . .
    C C21 0.10652(11) 0.4730(4) 0.5262(4) 0.0443(9) Uani d 1 . .
    C C22 0.14088(11) 0.4648(4) 0.4399(4) 0.0439(8) Uani d 1 . .
    C C23 0.18067(12) 0.5160(5) 0.4490(4) 0.0492(9) Uani d 1 . .
    H H23 0.1909 0.5688 0.5275 0.059 Uiso calc 1 . .
    C C24 0.20434(13) 0.4850(5) 0.3366(5) 0.0598(11) Uani d 1 . .
    C C25 0.19033(17) 0.4081(6) 0.2148(5) 0.0700(13) Uani d 1 . .
    H H25 0.2077 0.3899 0.1420 0.084 Uiso calc 1 . .
    C C26 0.15079(16) 0.3597(5) 0.2040(4) 0.0665(13) Uani d 1 . .
    H H26 0.1408 0.3085 0.1245 0.080 Uiso calc 1 . .
    C C27 0.12625(13) 0.3904(5) 0.3168(4) 0.0494(10) Uani d 1 . .
    C C28 0.05914(16) 0.2949(6) 0.2328(5) 0.0824(15) Uani d 1 . .
    H H28A 0.0331 0.2863 0.2733 0.124 Uiso calc 1 . .
    H H28B 0.0582 0.3758 0.1569 0.124 Uiso calc 1 . .
    H H28C 0.0674 0.1793 0.2017 0.124 Uiso calc 1 . .
    N N1 0.37717(10) 0.8847(4) 0.7771(3) 0.0524(8) Uani d 1 . .
    N N2 0.33801(11) 0.9220(4) 0.7986(3) 0.0552(8) Uani d 1 . .
    N N3 0.33657(14) 1.1181(5) 1.3406(4) 0.0670(11) Uani d 1 . .
    N N4 0.07439(10) 0.4110(4) 0.4608(4) 0.0560(9) Uani d 1 . .
    N N5 0.08741(11) 0.3607(4) 0.3338(4) 0.0592(9) Uani d 1 . .
    N N6 0.24577(14) 0.5381(7) 0.3419(5) 0.0853(13) Uani d 1 . .
    O O1 0.36862(12) 1.1219(5) 1.4003(4) 0.0835(10) Uani d 1 . .
    O O2 0.30487(11) 1.1535(6) 1.3978(4) 0.0990(12) Uani d 1 . .
    O O3 0.25797(11) 0.6241(6) 0.4405(5) 0.1101(14) Uani d 1 . .
    O O4 0.26727(13) 0.4964(8) 0.2468(5) 0.146(2) Uani d 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
    C1 C2 . 1.383(6) ?
    C1 C6 . 1.388(5) ?
    C1 H1 . 0.9300 ?
    C2 C3 . 1.388(8) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.372(7) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.380(6) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.399(6) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.465(5) ?
    C7 N1 . 1.319(5) ?
    C7 C8 . 1.433(5) ?
    C8 C13 . 1.403(5) ?
    C8 C9 . 1.403(6) ?
    C9 C10 . 1.366(6) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.391(6) ?
    C10 N3 . 1.466(5) ?
    C11 C12 . 1.367(7) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.396(6) ?
    C12 H12 . 0.9300 ?
    C13 N2 . 1.359(5) ?
    C14 N2 . 1.444(5) ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C15 C16 . 1.388(7) ?
    C15 C20 . 1.388(6) ?
    C15 H15 . 0.9300 ?
    C16 C17 . 1.365(7) ?
    C16 H16 . 0.9300 ?
    C17 C18 . 1.376(7) ?
    C17 H17 . 0.9300 ?
    C18 C19 . 1.377(6) ?
    C18 H18 . 0.9300 ?
    C19 C20 . 1.389(6) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.463(5) ?
    C21 N4 . 1.336(5) ?
    C21 C22 . 1.429(5) ?
    C22 C23 . 1.389(5) ?
    C22 C27 . 1.416(5) ?
    C23 C24 . 1.376(6) ?
    C23 H23 . 0.9300 ?
    C24 C25 . 1.404(7) ?
    C24 N6 . 1.444(6) ?
    C25 C26 . 1.377(6) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.396(6) ?
    C26 H26 . 0.9300 ?
    C27 N5 . 1.330(5) ?
    C28 N5 . 1.455(5) ?
    C28 H28A . 0.9600 ?
    C28 H28B . 0.9600 ?
    C28 H28C . 0.9600 ?
    N1 N2 . 1.357(4) ?
    N3 O1 . 1.222(5) ?
    N3 O2 . 1.229(4) ?
    N4 N5 . 1.371(5) ?
    N6 O4 . 1.218(6) ?
    N6 O3 . 1.231(6) ?
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
    C2 C1 C6 . . 120.7(4) ?
    C2 C1 H1 . . 119.7 ?
    C6 C1 H1 . . 119.7 ?
    C1 C2 C3 . . 120.2(5) ?
    C1 C2 H2 . . 119.9 ?
    C3 C2 H2 . . 119.9 ?
    C4 C3 C2 . . 119.4(4) ?
    C4 C3 H3 . . 120.3 ?
    C2 C3 H3 . . 120.3 ?
    C3 C4 C5 . . 121.0(5) ?
    C3 C4 H4 . . 119.5 ?
    C5 C4 H4 . . 119.5 ?
    C4 C5 C6 . . 120.2(4) ?
    C4 C5 H5 . . 119.9 ?
    C6 C5 H5 . . 119.9 ?
    C1 C6 C5 . . 118.5(4) ?
    C1 C6 C7 . . 119.2(4) ?
    C5 C6 C7 . . 122.2(3) ?
    N1 C7 C8 . . 110.1(3) ?
    N1 C7 C6 . . 119.4(3) ?
    C8 C7 C6 . . 130.5(4) ?
    C13 C8 C9 . . 118.7(4) ?
    C13 C8 C7 . . 104.6(3) ?
    C9 C8 C7 . . 136.6(4) ?
    C10 C9 C8 . . 117.3(4) ?
    C10 C9 H9 . . 121.3 ?
    C8 C9 H9 . . 121.3 ?
    C9 C10 C11 . . 123.6(4) ?
    C9 C10 N3 . . 118.3(4) ?
    C11 C10 N3 . . 118.0(4) ?
    C12 C11 C10 . . 120.2(4) ?
    C12 C11 H11 . . 119.9 ?
    C10 C11 H11 . . 119.9 ?
    C11 C12 C13 . . 117.2(4) ?
    C11 C12 H12 . . 121.4 ?
    C13 C12 H12 . . 121.4 ?
    N2 C13 C12 . . 130.5(4) ?
    N2 C13 C8 . . 106.6(4) ?
    C12 C13 C8 . . 122.9(4) ?
    N2 C14 H14A . . 109.5 ?
    N2 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    N2 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C16 C15 C20 . . 120.6(5) ?
    C16 C15 H15 . . 119.7 ?
    C20 C15 H15 . . 119.7 ?
    C17 C16 C15 . . 120.2(5) ?
    C17 C16 H16 . . 119.9 ?
    C15 C16 H16 . . 119.9 ?
    C16 C17 C18 . . 120.2(4) ?
    C16 C17 H17 . . 119.9 ?
    C18 C17 H17 . . 119.9 ?
    C17 C18 C19 . . 119.8(5) ?
    C17 C18 H18 . . 120.1 ?
    C19 C18 H18 . . 120.1 ?
    C18 C19 C20 . . 121.2(4) ?
    C18 C19 H19 . . 119.4 ?
    C20 C19 H19 . . 119.4 ?
    C15 C20 C19 . . 118.0(4) ?
    C15 C20 C21 . . 121.2(4) ?
    C19 C20 C21 . . 120.8(4) ?
    N4 C21 C22 . . 110.5(3) ?
    N4 C21 C20 . . 120.0(4) ?
    C22 C21 C20 . . 129.5(4) ?
    C23 C22 C27 . . 119.6(4) ?
    C23 C22 C21 . . 136.3(3) ?
    C27 C22 C21 . . 104.0(3) ?
    C24 C23 C22 . . 117.1(4) ?
    C24 C23 H23 . . 121.5 ?
    C22 C23 H23 . . 121.5 ?
    C23 C24 C25 . . 123.8(4) ?
    C23 C24 N6 . . 118.5(4) ?
    C25 C24 N6 . . 117.7(4) ?
    C26 C25 C24 . . 119.7(4) ?
    C26 C25 H25 . . 120.2 ?
    C24 C25 H25 . . 120.2 ?
    C25 C26 C27 . . 117.5(4) ?
    C25 C26 H26 . . 121.3 ?
    C27 C26 H26 . . 121.3 ?
    N5 C27 C26 . . 130.3(4) ?
    N5 C27 C22 . . 107.3(3) ?
    C26 C27 C22 . . 122.4(4) ?
    N5 C28 H28A . . 109.5 ?
    N5 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    N5 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C7 N1 N2 . . 107.3(3) ?
    N1 N2 C13 . . 111.4(3) ?
    N1 N2 C14 . . 120.1(3) ?
    C13 N2 C14 . . 128.5(4) ?
    O1 N3 O2 . . 122.4(4) ?
    O1 N3 C10 . . 119.4(4) ?
    O2 N3 C10 . . 118.3(5) ?
    C21 N4 N5 . . 106.0(3) ?
    C27 N5 N4 . . 112.2(3) ?
    C27 N5 C28 . . 127.5(4) ?
    N4 N5 C28 . . 120.2(4) ?
    O4 N6 O3 . . 122.6(5) ?
    O4 N6 C24 . . 118.0(6) ?
    O3 N6 C24 . . 119.4(4) ?
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
    C14 H14B O2 1_554 0.96 2.51 3.395(6) 153.6
    C19 H19 O4 4 0.93 2.46 3.288(6) 147.9
