##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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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#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     'SHELXL-97'
_journal_date_recd_electronic     2007-04-13
_journal_date_accepted     2007-04-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      5
_journal_page_first     o2742
_journal_page_last     o2742
_journal_paper_category     QO
_journal_coeditor_code     CI2366
_publ_contact_author_name     'Du-Lin Yin'
_publ_contact_author_address
;
College of Chemistry and Chemical Engineering
Hunan Normal University
Changsha, Hunan
People's Republic of China
;
_publ_contact_author_email     yindulin1957@hotmail.com
_publ_contact_author_fax     '86-(0516)-3403164'
_publ_contact_author_phone     '86-(0516)-3846996'
_publ_section_title
;
2-{4-[(E)-2,3-Diiodoallyl]-7-fluoro-3-oxo-3,4-dihydro-2H-
benzo[b][1,4]oxazin-6-yl}-2,3,4,5,6,7-hexahydro-1H-isoindole-
1,3-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Huai-Lin Pang' .
;
College of Chemistry and Chemical Engineering
Hunan Normal University
Changsha, Hunan
People's Republic of China
;
    'Yin Huang' .
;
College of Chemistry
Huazhong Normal University
Wuhan, Hubei
People's Republic of China
;
    'Du-Lin Yin' .
;
College of Chemistry and Chemical Engineering
Hunan Normal University
Changsha, Hunan
People's Republic of China
;
    'Hai Yang' .
;
College of Chemistry and Chemical Engineering
Hunan Normal University
Changsha, Hunan
People's Republic of China
;
    'Wen-An Li' .
;
College of Chemistry and Chemical Engineering
Hunan Normal University
Changsha, Hunan
People's Republic of China
;
data_I
_chemical_name_systematic
;
2-{4-[(E)-2,3-Diiodoallyl]-7-fluoro-3-oxo-3,4-dihydro-2H-
benzo[b][1,4]oxazin-6-yl}-2,3,4,5,6,7-hexahydro-1H-isoindole-
1,3-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H15 F I2 N2 O4'
_chemical_formula_sum     'C19 H15 F I2 N2 O4'
_chemical_formula_iupac     'C19 H15 F I2 N2 O4'
_chemical_formula_weight     608.13
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'C 2/c'
_symmetry_space_group_name_Hall     '-C 2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y, z-1/2'
    '-x+1/2, -y+1/2, -z'
    'x+1/2, -y+1/2, z-1/2'
_cell_length_a     23.118(4)
_cell_length_b     13.926(2)
_cell_length_c     14.975(3)
_cell_angle_alpha     90.00
_cell_angle_beta     123.266(2)
_cell_angle_gamma     90.00
_cell_volume     4030.9(12)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     5415
_cell_measurement_theta_min     2.74
_cell_measurement_theta_max     26.34
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.14
_exptl_crystal_density_diffrn     2.004
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     2320
_exptl_absorpt_coefficient_mu     3.157
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.7322
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11268
_diffrn_reflns_av_R_equivalents     0.0259
_diffrn_reflns_av_sigmaI/netI     0.0280
_diffrn_reflns_theta_min     1.80
_diffrn_reflns_theta_max     26.39
_diffrn_reflns_theta_full     26.39
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -28
_diffrn_reflns_limit_h_max     28
_diffrn_reflns_limit_k_min     -17
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     18
_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     4138
_reflns_number_gt     3361
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0414
_refine_ls_R_factor_gt     0.0301
_refine_ls_wR_factor_gt     0.0719
_refine_ls_wR_factor_ref     0.0787
_refine_ls_goodness_of_fit_ref     1.011
_refine_ls_restrained_S_all     1.011
_refine_ls_number_reflns     4138
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0354P)²+9.6041P] 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     1.048
_refine_diff_density_min     -0.846
_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'
    'F' 'F' 0.0171 0.0103
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'I' 'I' -0.4742 1.8119
                         '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, 1999)'
_computing_data_reduction     'SAINT'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL (Bruker, 1999)'
_computing_publication_material     'SHELXTL'
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
    I I1 0.085767(14) 0.79872(2) 0.22966(2) 0.05341(10) Uani d . 1 . .
    I I2 0.242669(15) 0.56013(2) 0.50881(3) 0.05973(11) Uani d . 1 . .
    F F1 0.09204(15) 0.8397(2) 0.7385(2) 0.0669(7) Uani d . 1 . .
    O O1 0.08081(17) 0.4150(2) 0.4174(3) 0.0632(8) Uani d . 1 . .
    O O2 0.06687(15) 0.51904(18) 0.6219(2) 0.0504(7) Uani d . 1 . .
    O O3 0.22865(16) 0.9158(2) 0.7464(3) 0.0718(10) Uani d . 1 . .
    O O4 0.02229(15) 0.9427(2) 0.4271(2) 0.0582(8) Uani d . 1 . .
    N N1 0.08795(15) 0.5729(2) 0.4618(2) 0.0383(7) Uani d . 1 . .
    N N2 0.11976(15) 0.9039(2) 0.5913(2) 0.0383(7) Uani d . 1 . .
    C C1 0.1654(2) 0.7084(3) 0.3419(3) 0.0482(9) Uani d . 1 . .
    H H1 0.2100 0.7189 0.3581 0.058 Uiso calc R 1 . .
    C C2 0.15559(18) 0.6375(3) 0.3907(3) 0.0401(8) Uani d . 1 . .
    C C3 0.08655(19) 0.6034(3) 0.3686(3) 0.0404(8) Uani d . 1 . .
    H H3A 0.0532 0.6551 0.3344 0.049 Uiso calc R 1 . .
    H H3B 0.0705 0.5503 0.3186 0.049 Uiso calc R 1 . .
    C C4 0.0862(2) 0.4759(3) 0.4793(3) 0.0451(9) Uani d . 1 . .
    C C5 0.0955(2) 0.4511(3) 0.5838(4) 0.0531(10) Uani d . 1 . .
    H H5A 0.0745 0.3890 0.5768 0.064 Uiso calc R 1 . .
    H H5B 0.1446 0.4449 0.6373 0.064 Uiso calc R 1 . .
    C C6 0.08179(17) 0.6133(3) 0.6143(3) 0.0392(8) Uani d . 1 . .
    C C7 0.0813(2) 0.6781(3) 0.6830(3) 0.0469(9) Uani d . 1 . .
    H H7 0.0733 0.6583 0.7347 0.056 Uiso calc R 1 . .
    C C8 0.0931(2) 0.7739(3) 0.6729(3) 0.0456(9) Uani d . 1 . .
    C C9 0.10596(18) 0.8049(2) 0.5982(3) 0.0364(7) Uani d . 1 . .
    C C10 0.10609(17) 0.7381(2) 0.5293(3) 0.0351(7) Uani d . 1 . .
    H H10 0.1151 0.7577 0.4788 0.042 Uiso calc R 1 . .
    C C11 0.09276(17) 0.6418(2) 0.5361(3) 0.0346(7) Uani d . 1 . .
    C C12 0.1811(2) 0.9511(3) 0.6655(3) 0.0432(9) Uani d . 1 . .
    C C13 0.17571(19) 1.0491(2) 0.6224(3) 0.0391(8) Uani d . 1 . .
    C C14 0.2311(2) 1.1238(3) 0.6715(3) 0.0547(11) Uani d . 1 . .
    H H14A 0.2717 1.1005 0.6745 0.066 Uiso calc R 1 . .
    H H14B 0.2442 1.1368 0.7439 0.066 Uiso calc R 1 . .
    C C15 0.2052(3) 1.2164(3) 0.6053(4) 0.0656(13) Uani d . 1 . .
    H H15A 0.1799 1.2538 0.6277 0.079 Uiso calc R 1 . .
    H H15B 0.2448 1.2542 0.6200 0.079 Uiso calc R 1 . .
    C C16 0.1595(3) 1.1994(3) 0.4877(4) 0.0638(12) Uani d . 1 . .
    H H16A 0.1853 1.1646 0.4643 0.077 Uiso calc R 1 . .
    H H16B 0.1459 1.2607 0.4509 0.077 Uiso calc R 1 . .
    C C17 0.0948(2) 1.1424(3) 0.4576(4) 0.0539(10) Uani d . 1 . .
    H H17A 0.0635 1.1822 0.4656 0.065 Uiso calc R 1 . .
    H H17B 0.0710 1.1218 0.3837 0.065 Uiso calc R 1 . .
    C C18 0.11612(19) 1.0573(2) 0.5290(3) 0.0366(8) Uani d . 1 . .
    C C19 0.07739(19) 0.9643(3) 0.5051(3) 0.0374(8) 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
    I1 C1 . 2.098(4) ?
    I2 C2 . 2.106(3) ?
    F1 C8 . 1.352(4) ?
    O1 C4 . 1.211(5) ?
    O2 C6 . 1.377(4) ?
    O2 C5 . 1.440(5) ?
    O3 C12 . 1.207(5) ?
    O4 C19 . 1.202(4) ?
    N1 C4 . 1.381(5) ?
    N1 C11 . 1.426(5) ?
    N1 C3 . 1.443(5) ?
    N2 C19 . 1.395(5) ?
    N2 C12 . 1.397(5) ?
    N2 C9 . 1.431(4) ?
    C1 C2 . 1.320(6) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.518(5) ?
    C3 H3A . 0.97 ?
    C3 H3B . 0.97 ?
    C4 C5 . 1.498(6) ?
    C5 H5A . 0.97 ?
    C5 H5B . 0.97 ?
    C6 C7 . 1.374(5) ?
    C6 C11 . 1.386(5) ?
    C7 C8 . 1.387(6) ?
    C7 H7 . 0.93 ?
    C8 C9 . 1.376(5) ?
    C9 C10 . 1.390(5) ?
    C10 C11 . 1.392(5) ?
    C10 H10 . 0.93 ?
    C12 C13 . 1.485(5) ?
    C13 C18 . 1.324(5) ?
    C13 C14 . 1.494(5) ?
    C14 C15 . 1.535(6) ?
    C14 H14A . 0.97 ?
    C14 H14B . 0.97 ?
    C15 C16 . 1.494(7) ?
    C15 H15A . 0.97 ?
    C15 H15B . 0.97 ?
    C16 C17 . 1.527(6) ?
    C16 H16A . 0.97 ?
    C16 H16B . 0.97 ?
    C17 C18 . 1.487(5) ?
    C17 H17A . 0.97 ?
    C17 H17B . 0.97 ?
    C18 C19 . 1.503(5) ?
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
    C6 O2 C5 . . 113.8(3) ?
    C4 N1 C11 . . 120.5(3) ?
    C4 N1 C3 . . 118.9(3) ?
    C11 N1 C3 . . 120.5(3) ?
    C19 N2 C12 . . 110.1(3) ?
    C19 N2 C9 . . 125.2(3) ?
    C12 N2 C9 . . 124.4(3) ?
    C2 C1 I1 . . 123.3(3) ?
    C2 C1 H1 . . 118.3 ?
    I1 C1 H1 . . 118.3 ?
    C1 C2 C3 . . 126.4(3) ?
    C1 C2 I2 . . 118.2(3) ?
    C3 C2 I2 . . 115.4(3) ?
    N1 C3 C2 . . 114.7(3) ?
    N1 C3 H3A . . 108.6 ?
    C2 C3 H3A . . 108.6 ?
    N1 C3 H3B . . 108.6 ?
    C2 C3 H3B . . 108.6 ?
    H3A C3 H3B . . 107.6 ?
    O1 C4 N1 . . 122.8(4) ?
    O1 C4 C5 . . 122.3(4) ?
    N1 C4 C5 . . 114.9(3) ?
    O2 C5 C4 . . 115.4(3) ?
    O2 C5 H5A . . 108.4 ?
    C4 C5 H5A . . 108.4 ?
    O2 C5 H5B . . 108.4 ?
    C4 C5 H5B . . 108.4 ?
    H5A C5 H5B . . 107.5 ?
    C7 C6 O2 . . 117.3(3) ?
    C7 C6 C11 . . 121.7(3) ?
    O2 C6 C11 . . 120.9(3) ?
    C6 C7 C8 . . 117.9(4) ?
    C6 C7 H7 . . 121.1 ?
    C8 C7 H7 . . 121.1 ?
    F1 C8 C9 . . 118.4(4) ?
    F1 C8 C7 . . 119.3(3) ?
    C9 C8 C7 . . 122.3(4) ?
    C8 C9 C10 . . 118.9(3) ?
    C8 C9 N2 . . 121.2(3) ?
    C10 C9 N2 . . 120.0(3) ?
    C9 C10 C11 . . 120.0(3) ?
    C9 C10 H10 . . 120.0 ?
    C11 C10 H10 . . 120.0 ?
    C6 C11 C10 . . 119.2(3) ?
    C6 C11 N1 . . 119.6(3) ?
    C10 C11 N1 . . 121.1(3) ?
    O3 C12 N2 . . 125.1(3) ?
    O3 C12 C13 . . 128.6(4) ?
    N2 C12 C13 . . 106.3(3) ?
    C18 C13 C12 . . 109.2(3) ?
    C18 C13 C14 . . 125.0(3) ?
    C12 C13 C14 . . 125.5(3) ?
    C13 C14 C15 . . 110.0(4) ?
    C13 C14 H14A . . 109.7 ?
    C15 C14 H14A . . 109.7 ?
    C13 C14 H14B . . 109.7 ?
    C15 C14 H14B . . 109.7 ?
    H14A C14 H14B . . 108.2 ?
    C16 C15 C14 . . 113.6(4) ?
    C16 C15 H15A . . 108.8 ?
    C14 C15 H15A . . 108.8 ?
    C16 C15 H15B . . 108.8 ?
    C14 C15 H15B . . 108.8 ?
    H15A C15 H15B . . 107.7 ?
    C15 C16 C17 . . 112.1(4) ?
    C15 C16 H16A . . 109.2 ?
    C17 C16 H16A . . 109.2 ?
    C15 C16 H16B . . 109.2 ?
    C17 C16 H16B . . 109.2 ?
    H16A C16 H16B . . 107.9 ?
    C18 C17 C16 . . 108.5(3) ?
    C18 C17 H17A . . 110.0 ?
    C16 C17 H17A . . 110.0 ?
    C18 C17 H17B . . 110.0 ?
    C16 C17 H17B . . 110.0 ?
    H17A C17 H17B . . 108.4 ?
    C13 C18 C17 . . 124.8(3) ?
    C13 C18 C19 . . 108.4(3) ?
    C17 C18 C19 . . 126.6(3) ?
    O4 C19 N2 . . 125.5(3) ?
    O4 C19 C18 . . 128.5(4) ?
    N2 C19 C18 . . 106.0(3) ?
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
    I1 C1 C2 C3 . . . . 5.7(6) ?
    I1 C1 C2 I2 . . . . -175.86(18) ?
    C4 N1 C3 C2 . . . . -104.5(4) ?
    C11 N1 C3 C2 . . . . 74.0(4) ?
    C1 C2 C3 N1 . . . . -143.5(4) ?
    I2 C2 C3 N1 . . . . 38.0(4) ?
    C11 N1 C4 O1 . . . . 178.6(3) ?
    C3 N1 C4 O1 . . . . -3.0(6) ?
    C11 N1 C4 C5 . . . . -4.8(5) ?
    C3 N1 C4 C5 . . . . 173.7(3) ?
    C6 O2 C5 C4 . . . . -45.6(5) ?
    O1 C4 C5 O2 . . . . -149.4(4) ?
    N1 C4 C5 O2 . . . . 33.9(5) ?
    C5 O2 C6 C7 . . . . -155.2(4) ?
    C5 O2 C6 C11 . . . . 28.5(5) ?
    O2 C6 C7 C8 . . . . -177.1(3) ?
    C11 C6 C7 C8 . . . . -0.8(6) ?
    C6 C7 C8 F1 . . . . 179.2(3) ?
    C6 C7 C8 C9 . . . . -1.0(6) ?
    F1 C8 C9 C10 . . . . -179.1(3) ?
    C7 C8 C9 C10 . . . . 1.1(6) ?
    F1 C8 C9 N2 . . . . 1.6(6) ?
    C7 C8 C9 N2 . . . . -178.3(4) ?
    C19 N2 C9 C8 . . . . -114.3(4) ?
    C12 N2 C9 C8 . . . . 72.4(5) ?
    C19 N2 C9 C10 . . . . 66.3(5) ?
    C12 N2 C9 C10 . . . . -107.0(4) ?
    C8 C9 C10 C11 . . . . 0.5(5) ?
    N2 C9 C10 C11 . . . . 179.9(3) ?
    C7 C6 C11 C10 . . . . 2.3(5) ?
    O2 C6 C11 C10 . . . . 178.5(3) ?
    C7 C6 C11 N1 . . . . -175.6(3) ?
    O2 C6 C11 N1 . . . . 0.6(5) ?
    C9 C10 C11 C6 . . . . -2.2(5) ?
    C9 C10 C11 N1 . . . . 175.7(3) ?
    C4 N1 C11 C6 . . . . -12.9(5) ?
    C3 N1 C11 C6 . . . . 168.6(3) ?
    C4 N1 C11 C10 . . . . 169.2(3) ?
    C3 N1 C11 C10 . . . . -9.3(5) ?
    C19 N2 C12 O3 . . . . -177.3(4) ?
    C9 N2 C12 O3 . . . . -3.1(6) ?
    C19 N2 C12 C13 . . . . 0.9(4) ?
    C9 N2 C12 C13 . . . . 175.1(3) ?
    O3 C12 C13 C18 . . . . 177.0(4) ?
    N2 C12 C13 C18 . . . . -1.1(4) ?
    O3 C12 C13 C14 . . . . 2.0(7) ?
    N2 C12 C13 C14 . . . . -176.1(4) ?
    C18 C13 C14 C15 . . . . 7.4(6) ?
    C12 C13 C14 C15 . . . . -178.3(4) ?
    C13 C14 C15 C16 . . . . -36.9(6) ?
    C14 C15 C16 C17 . . . . 60.0(6) ?
    C15 C16 C17 C18 . . . . -48.6(5) ?
    C12 C13 C18 C17 . . . . -174.8(4) ?
    C14 C13 C18 C17 . . . . 0.3(6) ?
    C12 C13 C18 C19 . . . . 0.8(4) ?
    C14 C13 C18 C19 . . . . 175.9(4) ?
    C16 C17 C18 C13 . . . . 20.0(6) ?
    C16 C17 C18 C19 . . . . -154.8(4) ?
    C12 N2 C19 O4 . . . . 177.5(4) ?
    C9 N2 C19 O4 . . . . 3.3(6) ?
    C12 N2 C19 C18 . . . . -0.4(4) ?
    C9 N2 C19 C18 . . . . -174.6(3) ?
    C13 C18 C19 O4 . . . . -178.1(4) ?
    C17 C18 C19 O4 . . . . -2.6(6) ?
    C13 C18 C19 N2 . . . . -0.3(4) ?
    C17 C18 C19 N2 . . . . 175.2(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
    _geom_hbond_publ_flag
    C5 H5B O3 4_546 0.97 2.49 3.449(7) 171 y
    C16 H16B O1 1_565 0.97 2.51 3.366(6) 147 y
    C17 H17B F1 6_575 0.97 2.53 3.256(6) 131 y
