##############################################################################
#                                                                            #
# 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     2012-03-31
_journal_date_accepted     2012-04-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2012
_journal_volume     68
_journal_issue      5
_journal_page_first     o1336
_journal_page_last     o1337
_journal_paper_category     QO
_journal_paper_doi     10.1107/S160053681201433X
_journal_coeditor_code     SJ5231
_publ_contact_author_name     'Hong-Yan Ban'
_publ_contact_author_address
;
School of Chemical Engineering
University of Science and Technology Liaoning
Anshan 114051
People's Republic of China
;
_publ_contact_author_email     hongyan_ban@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;\
N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole-5-\
carbohydrazide
;
loop_
    _publ_author_name
    _publ_author_address
    'Jiao Wei'
;
School of Chemical Engineering
University of Science and Technology Liaoning
Anshan 114051
People's Republic of China
;
    'Hong-Yan Ban'
;
School of Chemical Engineering
University of Science and Technology Liaoning
Anshan 114051
People's Republic of China
;
    'Xiao-Zhi Sun'
;
School of Chemical Engineering
University of Science and Technology Liaoning
Anshan 114051
People's Republic of China
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
N'-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole-
5-carbohydrazide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H10 Br Cl N2 O4'
_chemical_formula_sum     'C15 H10 Br Cl N2 O4'
_chemical_formula_iupac     'C15 H10 Br Cl N2 O4'
_chemical_formula_weight     397.61
_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     9.769(2)
_cell_length_b     13.041(3)
_cell_length_c     13.251(3)
_cell_angle_alpha     75.558(2)
_cell_angle_beta     78.745(2)
_cell_angle_gamma     76.527(2)
_cell_volume     1572.9(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2572
_cell_measurement_theta_min     2.45
_cell_measurement_theta_max     24.98
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.12
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.679
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     792
_exptl_absorpt_coefficient_mu     2.804
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7296
_exptl_absorpt_correction_T_max     0.7668
_exptl_special_details
;
;
_diffrn_ambient_temperature     298(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 SMART CCD area-detector'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     8062
_diffrn_reflns_av_R_equivalents     0.0189
_diffrn_reflns_av_sigmaI/netI     0.0441
_diffrn_reflns_theta_min     3.60
_diffrn_reflns_theta_max     25.50
_diffrn_reflns_theta_full     25.50
_diffrn_measured_fraction_theta_max     0.968
_diffrn_measured_fraction_theta_full     0.968
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     15
_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     5662
_reflns_number_gt     3817
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0786
_refine_ls_R_factor_gt     0.0482
_refine_ls_wR_factor_gt     0.1197
_refine_ls_wR_factor_ref     0.1372
_refine_ls_goodness_of_fit_ref     1.011
_refine_ls_restrained_S_all     1.011
_refine_ls_number_reflns     5662
_refine_ls_number_parameters     423
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0804P)²] 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     1.233
_refine_diff_density_min     -0.398
_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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
    '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     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1998)'
_computing_data_reduction     'SAINT (Bruker, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material     'SHELXTL (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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Br Br1 -0.32727(5) 0.72347(4) 1.11304(4) 0.0705(2) Uani d . 1 1 . .
    Br Br2 0.88064(7) -0.00317(5) 0.23324(6) 0.0941(3) Uani d . 1 1 . .
    Cl Cl1 0.21177(17) 0.81156(13) 1.05109(10) 0.0840(4) Uani d . 1 1 . .
    Cl Cl2 0.35756(17) 0.02462(10) 0.11594(10) 0.0753(4) Uani d . 1 1 . .
    N N1 0.0059(3) 0.5383(2) 0.8013(2) 0.0388(7) Uani d . 1 1 . .
    N N2 0.0549(3) 0.4803(2) 0.7245(2) 0.0388(7) Uani d D 1 1 . .
    N N3 0.5226(3) 0.3717(2) 0.3015(2) 0.0395(7) Uani d . 1 1 . .
    N N4 0.4588(3) 0.4720(2) 0.3202(3) 0.0404(7) Uani d D 1 1 . .
    O O1 -0.1949(3) 0.6081(2) 0.9379(2) 0.0517(7) Uani d . 1 1 . .
    H H1 -0.1559 0.5706 0.8951 0.078 Uiso calc R 1 1 . .
    O O2 -0.1698(3) 0.4846(2) 0.7053(2) 0.0543(7) Uani d . 1 1 . .
    O O3 0.7314(3) 0.2028(2) 0.2949(2) 0.0504(7) Uani d . 1 1 . .
    H H3 0.6932 0.2628 0.3057 0.076 Uiso calc R 1 1 . .
    O O4 0.6578(3) 0.4993(2) 0.3652(2) 0.0463(6) Uani d . 1 1 . .
    O O5 -0.0839(3) 0.2765(2) 0.4030(2) 0.0548(7) Uani d . 1 1 . .
    O O6 0.1385(3) 0.1716(2) 0.4079(3) 0.0657(9) Uani d . 1 1 . .
    O O7 0.4445(3) 0.8606(2) 0.4909(2) 0.0552(8) Uani d . 1 1 . .
    O O8 0.2603(3) 0.9451(2) 0.3952(3) 0.0622(8) Uani d . 1 1 . .
    C C1 0.0423(4) 0.6396(3) 0.9147(3) 0.0409(9) Uani d . 1 1 . .
    C C2 -0.0981(4) 0.6516(3) 0.9635(3) 0.0407(9) Uani d . 1 1 . .
    C C3 -0.1388(5) 0.7108(3) 1.0418(3) 0.0486(10) Uani d . 1 1 . .
    C C4 -0.0453(5) 0.7608(3) 1.0691(3) 0.0576(11) Uani d . 1 1 . .
    H H4 -0.0752 0.8024 1.1199 0.069 Uiso calc R 1 1 . .
    C C5 0.0917(6) 0.7474(4) 1.0197(3) 0.0557(11) Uani d . 1 1 . .
    C C6 0.1375(5) 0.6876(3) 0.9435(3) 0.0492(10) Uani d . 1 1 . .
    H H6 0.2318 0.6793 0.9113 0.059 Uiso calc R 1 1 . .
    C C7 0.0940(4) 0.5775(3) 0.8325(3) 0.0389(8) Uani d . 1 1 . .
    H H7 0.1896 0.5668 0.8035 0.047 Uiso calc R 1 1 . .
    C C8 -0.0431(4) 0.4514(3) 0.6826(3) 0.0374(8) Uani d . 1 1 . .
    C C9 0.0141(4) 0.3772(3) 0.6091(3) 0.0375(8) Uani d . 1 1 . .
    C C10 -0.0726(4) 0.3719(3) 0.5385(3) 0.0378(8) Uani d . 1 1 . .
    H H10 -0.1616 0.4166 0.5342 0.045 Uiso calc R 1 1 . .
    C C11 -0.0211(4) 0.2988(3) 0.4768(3) 0.0383(8) Uani d . 1 1 . .
    C C12 0.1124(4) 0.2353(3) 0.4811(3) 0.0481(10) Uani d . 1 1 . .
    C C13 0.1984(5) 0.2380(4) 0.5486(4) 0.0615(13) Uani d . 1 1 . .
    H H13 0.2874 0.1931 0.5513 0.074 Uiso calc R 1 1 . .
    C C14 0.1469(4) 0.3115(3) 0.6138(3) 0.0511(10) Uani d . 1 1 . .
    H H14 0.2027 0.3164 0.6612 0.061 Uiso calc R 1 1 . .
    C C15 0.0072(5) 0.1843(4) 0.3712(4) 0.0587(12) Uani d . 1 1 . .
    H H15A -0.0344 0.1207 0.4013 0.070 Uiso calc R 1 1 . .
    H H15B 0.0218 0.1947 0.2950 0.070 Uiso calc R 1 1 . .
    C C16 0.5024(4) 0.2181(3) 0.2431(3) 0.0416(9) Uani d . 1 1 . .
    C C17 0.6426(4) 0.1645(3) 0.2551(3) 0.0420(9) Uani d . 1 1 . .
    C C18 0.6890(5) 0.0671(3) 0.2240(3) 0.0537(11) Uani d . 1 1 . .
    C C19 0.6042(6) 0.0232(3) 0.1819(4) 0.0625(12) Uani d . 1 1 . .
    H H19 0.6384 -0.0424 0.1613 0.075 Uiso calc R 1 1 . .
    C C20 0.4687(5) 0.0778(3) 0.1709(3) 0.0518(10) Uani d . 1 1 . .
    C C21 0.4175(5) 0.1738(3) 0.2008(3) 0.0486(10) Uani d . 1 1 . .
    H H21 0.3248 0.2097 0.1928 0.058 Uiso calc R 1 1 . .
    C C22 0.4453(4) 0.3235(3) 0.2702(3) 0.0432(9) Uani d . 1 1 . .
    H H22 0.3508 0.3557 0.2645 0.052 Uiso calc R 1 1 . .
    C C23 0.5344(4) 0.5333(3) 0.3475(3) 0.0359(8) Uani d . 1 1 . .
    C C24 0.4563(4) 0.6435(3) 0.3554(3) 0.0339(8) Uani d . 1 1 . .
    C C25 0.4952(4) 0.6931(3) 0.4253(3) 0.0376(8) Uani d . 1 1 . .
    H H25 0.5668 0.6581 0.4661 0.045 Uiso calc R 1 1 . .
    C C26 0.4240(4) 0.7935(3) 0.4306(3) 0.0395(9) Uani d . 1 1 . .
    C C27 0.3156(4) 0.8472(3) 0.3720(3) 0.0416(9) Uani d . 1 1 . .
    C C28 0.2767(4) 0.8009(3) 0.3039(3) 0.0453(9) Uani d . 1 1 . .
    H H28 0.2038 0.8368 0.2646 0.054 Uiso calc R 1 1 . .
    C C29 0.3496(4) 0.6983(3) 0.2953(3) 0.0411(9) Uani d . 1 1 . .
    H H29 0.3265 0.6652 0.2480 0.049 Uiso calc R 1 1 . .
    C C30 0.3443(5) 0.9591(3) 0.4641(4) 0.0557(11) Uani d . 1 1 . .
    H H30A 0.2843 0.9769 0.5273 0.067 Uiso calc R 1 1 . .
    H H30B 0.3942 1.0177 0.4303 0.067 Uiso calc R 1 1 . .
    H H2 0.146(2) 0.472(4) 0.693(4) 0.080 Uiso d D 1 1 . .
    H H4A 0.3647(15) 0.492(4) 0.319(4) 0.080 Uiso d 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
    Br1 C3 . 1.888(4) ?
    Br2 C18 . 1.896(4) ?
    Cl1 C5 . 1.752(5) ?
    Cl2 C20 . 1.761(4) ?
    N1 C7 . 1.274(5) ?
    N1 N2 . 1.365(4) ?
    N2 C8 . 1.359(5) ?
    N2 H2 . 0.899(10) ?
    N3 C22 . 1.268(5) ?
    N3 N4 . 1.372(4) ?
    N4 C23 . 1.355(5) ?
    N4 H4A . 0.898(10) ?
    O1 C2 . 1.343(5) ?
    O1 H1 . 0.8200 ?
    O2 C8 . 1.216(4) ?
    O3 C17 . 1.338(5) ?
    O3 H3 . 0.8200 ?
    O4 C23 . 1.231(4) ?
    O5 C11 . 1.370(4) ?
    O5 C15 . 1.422(5) ?
    O6 C12 . 1.379(4) ?
    O6 C15 . 1.419(5) ?
    O7 C26 . 1.392(4) ?
    O7 C30 . 1.434(5) ?
    O8 C27 . 1.351(4) ?
    O8 C30 . 1.410(5) ?
    C1 C2 . 1.388(5) ?
    C1 C6 . 1.390(6) ?
    C1 C7 . 1.459(5) ?
    C2 C3 . 1.389(5) ?
    C3 C4 . 1.383(6) ?
    C4 C5 . 1.363(7) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.372(6) ?
    C6 H6 . 0.9300 ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.484(5) ?
    C9 C14 . 1.381(5) ?
    C9 C10 . 1.403(5) ?
    C10 C11 . 1.354(5) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.376(5) ?
    C12 C13 . 1.352(6) ?
    C13 C14 . 1.392(6) ?
    C13 H13 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 C21 . 1.379(5) ?
    C16 C17 . 1.405(6) ?
    C16 C22 . 1.464(5) ?
    C17 C18 . 1.381(5) ?
    C18 C19 . 1.373(6) ?
    C19 C20 . 1.365(7) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.362(6) ?
    C21 H21 . 0.9300 ?
    C22 H22 . 0.9300 ?
    C23 C24 . 1.481(5) ?
    C24 C29 . 1.388(5) ?
    C24 C25 . 1.405(5) ?
    C25 C26 . 1.343(5) ?
    C25 H25 . 0.9300 ?
    C26 C27 . 1.385(5) ?
    C27 C28 . 1.355(5) ?
    C28 C29 . 1.383(5) ?
    C28 H28 . 0.9300 ?
    C29 H29 . 0.9300 ?
    C30 H30A . 0.9700 ?
    C30 H30B . 0.9700 ?
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
    C7 N1 N2 . . 118.6(3) ?
    C8 N2 N1 . . 117.5(3) ?
    C8 N2 H2 . . 120(3) ?
    N1 N2 H2 . . 121(3) ?
    C22 N3 N4 . . 115.6(3) ?
    C23 N4 N3 . . 120.5(3) ?
    C23 N4 H4A . . 122(3) ?
    N3 N4 H4A . . 117(3) ?
    C2 O1 H1 . . 109.5 ?
    C17 O3 H3 . . 109.5 ?
    C11 O5 C15 . . 105.9(3) ?
    C12 O6 C15 . . 106.2(3) ?
    C26 O7 C30 . . 105.0(3) ?
    C27 O8 C30 . . 106.7(3) ?
    C2 C1 C6 . . 120.0(3) ?
    C2 C1 C7 . . 121.7(3) ?
    C6 C1 C7 . . 118.3(4) ?
    O1 C2 C1 . . 122.5(3) ?
    O1 C2 C3 . . 119.2(4) ?
    C1 C2 C3 . . 118.3(4) ?
    C4 C3 C2 . . 121.9(4) ?
    C4 C3 Br1 . . 119.1(3) ?
    C2 C3 Br1 . . 119.0(3) ?
    C5 C4 C3 . . 118.3(4) ?
    C5 C4 H4 . . 120.8 ?
    C3 C4 H4 . . 120.8 ?
    C4 C5 C6 . . 121.8(4) ?
    C4 C5 Cl1 . . 119.3(3) ?
    C6 C5 Cl1 . . 118.8(4) ?
    C5 C6 C1 . . 119.6(4) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    N1 C7 C1 . . 118.8(3) ?
    N1 C7 H7 . . 120.6 ?
    C1 C7 H7 . . 120.6 ?
    O2 C8 N2 . . 121.2(3) ?
    O2 C8 C9 . . 122.8(3) ?
    N2 C8 C9 . . 115.9(3) ?
    C14 C9 C10 . . 121.0(3) ?
    C14 C9 C8 . . 120.6(3) ?
    C10 C9 C8 . . 118.3(3) ?
    C11 C10 C9 . . 117.0(3) ?
    C11 C10 H10 . . 121.5 ?
    C9 C10 H10 . . 121.5 ?
    C10 C11 O5 . . 128.8(3) ?
    C10 C11 C12 . . 121.2(3) ?
    O5 C11 C12 . . 109.9(3) ?
    C13 C12 C11 . . 123.2(3) ?
    C13 C12 O6 . . 128.1(3) ?
    C11 C12 O6 . . 108.7(3) ?
    C12 C13 C14 . . 116.6(4) ?
    C12 C13 H13 . . 121.7 ?
    C14 C13 H13 . . 121.7 ?
    C9 C14 C13 . . 120.9(4) ?
    C9 C14 H14 . . 119.6 ?
    C13 C14 H14 . . 119.6 ?
    O6 C15 O5 . . 107.1(3) ?
    O6 C15 H15A . . 110.3 ?
    O5 C15 H15A . . 110.3 ?
    O6 C15 H15B . . 110.3 ?
    O5 C15 H15B . . 110.3 ?
    H15A C15 H15B . . 108.6 ?
    C21 C16 C17 . . 120.1(3) ?
    C21 C16 C22 . . 118.5(3) ?
    C17 C16 C22 . . 121.3(3) ?
    O3 C17 C18 . . 119.3(4) ?
    O3 C17 C16 . . 123.4(3) ?
    C18 C17 C16 . . 117.3(4) ?
    C19 C18 C17 . . 122.5(4) ?
    C19 C18 Br2 . . 119.5(3) ?
    C17 C18 Br2 . . 117.9(3) ?
    C20 C19 C18 . . 118.7(4) ?
    C20 C19 H19 . . 120.7 ?
    C18 C19 H19 . . 120.7 ?
    C21 C20 C19 . . 121.2(4) ?
    C21 C20 Cl2 . . 118.9(4) ?
    C19 C20 Cl2 . . 119.9(3) ?
    C20 C21 C16 . . 120.2(4) ?
    C20 C21 H21 . . 119.9 ?
    C16 C21 H21 . . 119.9 ?
    N3 C22 C16 . . 121.1(3) ?
    N3 C22 H22 . . 119.5 ?
    C16 C22 H22 . . 119.5 ?
    O4 C23 N4 . . 122.4(3) ?
    O4 C23 C24 . . 122.8(3) ?
    N4 C23 C24 . . 114.7(3) ?
    C29 C24 C25 . . 120.1(3) ?
    C29 C24 C23 . . 122.1(3) ?
    C25 C24 C23 . . 117.8(3) ?
    C26 C25 C24 . . 116.8(3) ?
    C26 C25 H25 . . 121.6 ?
    C24 C25 H25 . . 121.6 ?
    C25 C26 C27 . . 123.0(3) ?
    C25 C26 O7 . . 128.1(3) ?
    C27 C26 O7 . . 108.9(3) ?
    O8 C27 C28 . . 128.5(3) ?
    O8 C27 C26 . . 110.4(3) ?
    C28 C27 C26 . . 121.1(3) ?
    C27 C28 C29 . . 117.4(3) ?
    C27 C28 H28 . . 121.3 ?
    C29 C28 H28 . . 121.3 ?
    C28 C29 C24 . . 121.6(3) ?
    C28 C29 H29 . . 119.2 ?
    C24 C29 H29 . . 119.2 ?
    O8 C30 O7 . . 108.6(3) ?
    O8 C30 H30A . . 110.0 ?
    O7 C30 H30A . . 110.0 ?
    O8 C30 H30B . . 110.0 ?
    O7 C30 H30B . . 110.0 ?
    H30A C30 H30B . . 108.4 ?
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
    N2 H2 O4 2_666 0.899(10) 2.00(2) 2.872(4) 162(5)
    O3 H3 N3 . 0.82 1.92 2.637(4) 145.3
    O1 H1 N1 . 0.82 1.85 2.561(4) 145.0
