##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'manual editing of SHELXL-97 .cif file'
_journal_date_recd_electronic     2001-12-13
_journal_date_accepted     2001-12-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2002
_journal_volume     58
_journal_issue      2
_journal_page_first     o98
_journal_page_last     o101
_journal_paper_category     EO
_publ_contact_author_name     'Rafal Kruszynski'
_publ_contact_author_address
;
Institute of General and Ecological Chemistry
Technical University of Lodz
ul. Zeromskiego 116
90-924 Lodz
Poland
;
_publ_contact_author_email     kruszyna@ck-sg.p.lodz.pl
_publ_contact_author_fax     '(48-42) 631 31 03'
_publ_contact_author_phone     '(48-42) 631 31 37'
_publ_section_title
;
4-[(4-Ethoxyphenyl)aminoacetyl]-1,2,3,4-tetrahydroquinoxalin-2-one
;
loop_
    _publ_author_name
    _publ_author_address
    'Kruszynski, Rafal'
;Institute of General and Ecological Chemistry
 Technical University of Łódź
 ul. Żeromskiego 116
 90-924 Łódź
 Poland
;
    'Bartczak, Tadeusz J.'
;Institute of General and Ecological Chemistry
 Technical University of Łódź
 ul. Żeromskiego 116
 90-924 Łódź
 Poland
;
    'Mikiciuk-Olasik, Elżbieta'
;Department of Chemical Technology of Drugs
 Medical University of Łódź
 ul. Muszyńskiego 1
 90-145 Łódź
 Poland
;
data_V
_chemical_name_systematic
;4-(2-Acetyl-2-(4-ethoxyphenyl)amino-1-oxoethyl)-1,2,3,4-
tetrahydro-2-quinoxalinone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C20 H21 N3 O4'
_chemical_formula_sum     'C20 H21 N3 O4'
_chemical_formula_iupac     'C20 H21 N3 O4'
_chemical_formula_weight     367.40
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     8.2890(10)
_cell_length_b     12.117(2)
_cell_length_c     19.225(3)
_cell_angle_alpha     90.00
_cell_angle_beta     99.880(10)
_cell_angle_gamma     90.00
_cell_volume     1902.3(5)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     99
_cell_measurement_theta_min     5
_cell_measurement_theta_max     60
_cell_measurement_temperature     293(2)
_exptl_crystal_description     sphere
_exptl_crystal_colour     colourless
_exptl_crystal_size_rad      .51
_exptl_crystal_density_diffrn     1.283
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     776
_exptl_absorpt_coefficient_mu      .746
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(X-RED; Stoe & Cie, 1999)'
_exptl_absorpt_correction_T_min      .692
_exptl_absorpt_correction_T_max      .715
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     'Cu K\a'
_diffrn_radiation_wavelength     1.54052
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Kuma KM-4'
_diffrn_measurement_method     ω-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4204
_diffrn_reflns_av_R_equivalents      .0343
_diffrn_reflns_av_sigmaI/netI      .0607
_diffrn_reflns_theta_min     4.33
_diffrn_reflns_theta_max     80.59
_diffrn_reflns_theta_full     80.59
_diffrn_measured_fraction_theta_max      .890
_diffrn_measured_fraction_theta_full      .889
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     2
_diffrn_standards_interval_count     100
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     -4.0
_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     3916
_reflns_number_gt     1952
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all      .1625
_refine_ls_R_factor_gt      .0742
_refine_ls_wR_factor_gt      .2184
_refine_ls_wR_factor_ref      .2477
_refine_ls_goodness_of_fit_ref      .962
_refine_ls_restrained_S_all      .962
_refine_ls_number_reflns     3916
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                  'w = 1/[σ²(Fo²)+(0.1581P)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      .006
_refine_ls_shift/su_mean      .000
_refine_diff_density_max      .576
_refine_diff_density_min      -.330
_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'  .0181  .0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H'  .0000  .0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N'  .0311  .0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O'  .0492  .0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'KM-4 Software (Kuma, 1993)'
_computing_cell_refinement     'KM-4 Software'
_computing_data_reduction     'DATAPROC (Gałdecki et al, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1990a)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics
              'XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia, 1997)'
loop_
    _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
    _atom_site_type_symbol
    N12  .6189(3)  .7165(2)  .13601(15)  .0485(6) Uani d . 1 . . N
    C21  .5487(4)  .7771(3)  .1819(2)  .0564(8) Uani d . 1 . . C
    O13  .4613(3)  .7330(2)  .21980(14)  .0674(7) Uani d . 1 . . O
    C22  .5818(6)  .8990(3)  .1872(3)  .0767(12) Uani d . 1 . . C
    H22A  .6972  .9119  .1907  .092 Uiso calc R 1 . . H
    H22B  .5453  .9279  .2283  .092 Uiso calc R 1 . . H
    H22C  .5241  .9351  .1458  .092 Uiso calc R 1 . . H
    C12  .5837(4)  .5990(2)  .13085(18)  .0459(7) Uani d . 1 . . C
    H12A  .5941  .5677  .1779  .055 Uiso calc R 1 . . H
    H12B  .6624  .5626  .1066  .055 Uiso calc R 1 . . H
    C11  .4122(4)  .5786(3)  .09102(17)  .0479(7) Uani d . 1 . . C
    O11  .3327(3)  .6527(2)  .05875(16)  .0746(8) Uani d . 1 . . O
    N1  .3484(3)  .4755(2)  .09372(14)  .0465(6) Uani d . 1 . . N
    C8  .1713(4)  .4615(3)  .06975(19)  .0574(9) Uani d . 1 . . C
    H8A  .1532  .4065  .0325  .069 Uiso calc R 1 . . H
    H8B  .1248  .5306  .0504  .069 Uiso calc R 1 . . H
    C7  .0872(4)  .4264(3)  .1285(2)  .0615(10) Uani d . 1 . . C
    O1  -.0516(3)  .4530(3)  .1315(2)  .0998(11) Uani d . 1 . . O
    N2  .1776(4)  .3617(3)  .17842(19)  .0591(8) Uani d . 1 . . N
    H3  .135(5)  .325(4)  .204(2)  .077(14) Uiso d . 1 . . H
    C6  .3362(4)  .3262(3)  .17427(17)  .0478(7) Uani d . 1 . . C
    C1  .4261(4)  .3832(2)  .13107(17)  .0459(7) Uani d . 1 . . C
    C2  .5806(4)  .3460(3)  .1232(2)  .0559(9) Uani d . 1 . . C
    H2  .6379  .3806  .0918  .067 Uiso calc R 1 . . H
    C3  .6476(5)  .2573(3)  .1625(3)  .0719(12) Uani d . 1 . . C
    H3A  .7519  .2329  .1583  .086 Uiso calc R 1 . . H
    C4  .5623(5)  .2043(3)  .2081(2)  .0703(11) Uani d . 1 . . C
    H4  .6106  .1458  .2353  .084 Uiso calc R 1 . . H
    C5  .4061(5)  .2371(3)  .2136(2)  .0612(9) Uani d . 1 . . C
    H5  .3478  .1998  .2436  .073 Uiso calc R 1 . . H
    C13  .6987(4)  .7639(3)  .08156(18)  .0550(8) Uani d . 1 . . C
    C18  .8668(5)  .7447(3)  .0833(2)  .0610(9) Uani d . 1 . . C
    H18  .9247  .7028  .1198  .073 Uiso calc R 1 . . H
    C17  .9453(5)  .7855(4)  .0335(2)  .0733(11) Uani d . 1 . . C
    H17 1.0555  .7695  .0346  .088 Uiso calc R 1 . . H
    C16  .8651(5)  .8491(4)  -.0176(2)  .0724(12) Uani d . 1 . . C
    C15  .7003(7)  .8703(4)  -.0238(2)  .0884(15) Uani d . 1 . . C
    H15  .6462  .9126  -.0610  .106 Uiso calc R 1 . . H
    C14  .6124(6)  .8251(3)  .0289(2)  .0774(12) Uani d . 1 . . C
    H14  .5009  .8378  .0265  .093 Uiso calc R 1 . . H
    O12  .9570(4)  .8877(3)  -.06865(19)  .1013(11) Uani d . 1 . . O
    C19  .8841(8)  .9603(4)  -.1158(3)  .1053(18) Uani d . 1 . . C
    H19A  .8537 1.0256  -.0918  .126 Uiso calc R 1 . . H
    H19B  .7854  .9283  -.1425  .126 Uiso calc R 1 . . H
    C20 1.0017(7)  .9920(4)  -.1656(3)  .0962(16) Uani d . 1 . . C
    H20A  .9531 1.0489  -.1972  .115 Uiso calc R 1 . . H
    H20B 1.0235  .9285  -.1923  .115 Uiso calc R 1 . . H
    H20C 1.1024 1.0186  -.1385  .115 Uiso calc R 1 . . H
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    N12  .0395(15)  .0437(13)  .0646(16)  -.0056(10)  .0153(12)  -.0047(12)
    C21  .050(2)  .0485(17)  .073(2)  -.0019(15)  .0162(17)  .0002(17)
    O13  .0607(16)  .0601(15)  .0901(18)  -.0025(12)  .0379(14)  .0010(13)
    C22  .090(3)  .0451(19)  .102(3)  -.0049(19)  .039(3)  -.008(2)
    C12  .0352(16)  .0406(15)  .0628(19)  -.0038(12)  .0110(13)  .0005(13)
    C11  .0434(18)  .0477(17)  .0531(17)  -.0012(13)  .0098(14)  .0023(14)
    O11  .0546(15)  .0594(15)  .103(2)  -.0041(11)  -.0069(14)  .0292(14)
    N1  .0294(13)  .0459(13)  .0627(15)  -.0012(10)  .0035(11)  .0017(12)
    C8  .0340(18)  .062(2)  .071(2)  -.0068(14)  -.0042(15)  .0063(17)
    C7  .0266(17)  .066(2)  .090(3)  -.0063(15)  .0063(16)  .005(2)
    O1  .0327(15)  .113(3)  .155(3)  .0056(15)  .0225(17)  .032(2)
    N2  .0405(17)  .0590(17)  .080(2)  -.0048(13)  .0158(15)  .0079(16)
    C6  .0338(16)  .0477(16)  .0605(18)  -.0039(13)  .0039(13)  -.0067(14)
    C1  .0368(17)  .0382(14)  .0611(18)  -.0029(12)  .0035(13)  -.0066(13)
    C2  .0377(18)  .0460(16)  .085(2)  -.0005(13)  .0132(16)  -.0083(17)
    C3  .0398(19)  .0516(19)  .121(3)  .0065(15)  .005(2)  -.005(2)
    C4  .060(2)  .0447(18)  .098(3)  .0034(16)  -.011(2)  .0023(19)
    C5  .058(2)  .0508(19)  .072(2)  -.0066(16)  .0013(17)  .0069(17)
    C13  .059(2)  .0455(17)  .062(2)  -.0134(15)  .0143(17)  -.0052(15)
    C18  .055(2)  .062(2)  .070(2)  -.0146(16)  .0243(18)  -.0118(17)
    C17  .066(3)  .077(3)  .081(3)  -.009(2)  .025(2)  -.009(2)
    C16  .065(3)  .078(3)  .081(3)  -.032(2)  .030(2)  -.012(2)
    C15  .121(4)  .068(3)  .068(3)  -.022(3)  -.006(3)  .011(2)
    C14  .081(3)  .068(2)  .082(3)  -.015(2)  .010(2)  .010(2)
    O12  .104(3)  .101(3)  .102(2)  -.008(2)  .025(2)  .017(2)
    C19  .141(5)  .070(3)  .090(3)  -.023(3)  -.020(3)  -.008(3)
    C20  .132(5)  .082(3)  .085(3)  -.022(3)  .048(3)  .007(2)
_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
    N12 C21 . 1.354(4) no
    N12 C13 . 1.449(4) no
    N12 C12 . 1.454(4) no
    C21 O13 . 1.234(4) no
    C21 C22 . 1.502(5) no
    C22 H22A .  .9600 no
    C22 H22B .  .9600 no
    C22 H22C .  .9600 no
    C12 C11 . 1.515(4) no
    C12 H12A .  .9700 no
    C12 H12B .  .9700 no
    C11 O11 . 1.219(4) no
    C11 N1 . 1.361(4) no
    N1 C1 . 1.422(4) no
    N1 C8 . 1.470(4) no
    C8 C7 . 1.487(5) no
    C8 H8A .  .9700 no
    C8 H8B .  .9700 no
    C7 O1 . 1.206(4) no
    C7 N2 . 1.361(5) no
    N2 C6 . 1.398(4) no
    N2 H3 .  .78(4) no
    C6 C5 . 1.387(5) no
    C6 C1 . 1.391(4) no
    C1 C2 . 1.391(4) no
    C2 C3 . 1.375(5) no
    C2 H2 .  .9300 no
    C3 C4 . 1.375(6) no
    C3 H3A .  .9300 no
    C4 C5 . 1.376(5) no
    C4 H4 .  .9300 no
    C5 H5 .  .9300 no
    C13 C14 . 1.356(5) no
    C13 C18 . 1.407(5) no
    C18 C17 . 1.342(5) no
    C18 H18 .  .9300 no
    C17 C16 . 1.332(6) no
    C17 H17 .  .9300 no
    C16 C15 . 1.375(7) no
    C16 O12 . 1.421(5) no
    C15 C14 . 1.452(6) no
    C15 H15 .  .9300 no
    C14 H14 .  .9300 no
    O12 C19 . 1.331(6) no
    C19 C20 . 1.528(7) no
    C19 H19A .  .9700 no
    C19 H19B .  .9700 no
    C20 H20A .  .9600 no
    C20 H20B .  .9600 no
    C20 H20C .  .9600 no
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
    C21 N12 C13 . . 123.8(3) no
    C21 N12 C12 . . 118.2(3) no
    C13 N12 C12 . . 116.8(3) no
    O13 C21 N12 . . 120.8(3) no
    O13 C21 C22 . . 120.4(3) no
    N12 C21 C22 . . 118.9(3) no
    C21 C22 H22A . . 109.5 no
    C21 C22 H22B . . 109.5 no
    H22A C22 H22B . . 109.5 no
    C21 C22 H22C . . 109.5 no
    H22A C22 H22C . . 109.5 no
    H22B C22 H22C . . 109.5 no
    N12 C12 C11 . . 110.8(3) no
    N12 C12 H12A . . 109.5 no
    C11 C12 H12A . . 109.5 no
    N12 C12 H12B . . 109.5 no
    C11 C12 H12B . . 109.5 no
    H12A C12 H12B . . 108.1 no
    O11 C11 N1 . . 121.1(3) no
    O11 C11 C12 . . 121.0(3) no
    N1 C11 C12 . . 117.9(3) no
    C11 N1 C1 . . 126.5(2) no
    C11 N1 C8 . . 117.9(3) no
    C1 N1 C8 . . 114.1(3) no
    N1 C8 C7 . . 111.6(3) no
    N1 C8 H8A . . 109.3 no
    C7 C8 H8A . . 109.3 no
    N1 C8 H8B . . 109.3 no
    C7 C8 H8B . . 109.3 no
    H8A C8 H8B . . 108.0 no
    O1 C7 N2 . . 122.3(4) no
    O1 C7 C8 . . 122.4(4) no
    N2 C7 C8 . . 115.3(3) no
    C7 N2 C6 . . 123.1(3) no
    C7 N2 H3 . . 121(3) no
    C6 N2 H3 . . 113(3) no
    C5 C6 C1 . . 119.8(3) no
    C5 C6 N2 . . 121.1(3) no
    C1 C6 N2 . . 119.1(3) no
    C2 C1 C6 . . 120.1(3) no
    C2 C1 N1 . . 123.1(3) no
    C6 C1 N1 . . 116.7(3) no
    C3 C2 C1 . . 119.1(3) no
    C3 C2 H2 . . 120.4 no
    C1 C2 H2 . . 120.4 no
    C2 C3 C4 . . 120.8(3) no
    C2 C3 H3A . . 119.6 no
    C4 C3 H3A . . 119.6 no
    C3 C4 C5 . . 120.5(3) no
    C3 C4 H4 . . 119.7 no
    C5 C4 H4 . . 119.7 no
    C4 C5 C6 . . 119.5(3) no
    C4 C5 H5 . . 120.2 no
    C6 C5 H5 . . 120.2 no
    C14 C13 C18 . . 120.1(4) no
    C14 C13 N12 . . 120.6(3) no
    C18 C13 N12 . . 119.3(3) no
    C17 C18 C13 . . 121.4(4) no
    C17 C18 H18 . . 119.3 no
    C13 C18 H18 . . 119.3 no
    C16 C17 C18 . . 119.8(4) no
    C16 C17 H17 . . 120.1 no
    C18 C17 H17 . . 120.1 no
    C17 C16 C15 . . 122.4(4) no
    C17 C16 O12 . . 116.1(4) no
    C15 C16 O12 . . 121.3(4) no
    C16 C15 C14 . . 118.6(4) no
    C16 C15 H15 . . 120.7 no
    C14 C15 H15 . . 120.7 no
    C13 C14 C15 . . 117.6(4) no
    C13 C14 H14 . . 121.2 no
    C15 C14 H14 . . 121.2 no
    C19 O12 C16 . . 117.0(5) no
    O12 C19 C20 . . 109.2(5) no
    O12 C19 H19A . . 109.8 no
    C20 C19 H19A . . 109.8 no
    O12 C19 H19B . . 109.8 no
    C20 C19 H19B . . 109.8 no
    H19A C19 H19B . . 108.3 no
    C19 C20 H20A . . 109.5 no
    C19 C20 H20B . . 109.5 no
    H20A C20 H20B . . 109.5 no
    C19 C20 H20C . . 109.5 no
    H20A C20 H20C . . 109.5 no
    H20B C20 H20C . . 109.5 no
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
    C1 C6 N2 C7 . . . . 20.2(5) yes
    C6 N2 C7 C8 . . . . -2.5(5) yes
    N2 C7 C8 N1 . . . . -32.3(4) yes
    C7 C8 N1 C1 . . . . 51.6(4) yes
    C8 N1 C1 C6 . . . . -35.7(4) yes
    N1 C1 C6 N2 . . . .  .1(4) yes
    C1 N1 C11 O11 . . . . -178.0(3) yes
    C8 N1 C11 O11 . . . . -12.6(5) yes
    C1 N1 C11 C12 . . . .  .6(5) yes
    C8 N1 C11 C12 . . . . 166.0(3) yes
    N1 C11 C12 N12 . . . . -167.1(3) yes
    C11 C12 N12 C21 . . . . 74.5(4) yes
    C11 C12 N12 C13 . . . . -93.1(3) yes
    C12 N12 C13 C18 . . . . -75.5(4) yes
    C12 N12 C13 C14 . . . . 103.6(4) yes
    C15 C16 O12 C19 . . . . 11.1(6) yes
    C17 C16 O12 C19 . . . . -173.2(4) yes
    C16 O12 C19 C20 . . . . 179.8(4) yes
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
    C8 H8B O11 .  .97 2.26 2.702(4) 107
    N2 H3 O13 2_545  .78(4) 2.11(4) 2.891(4) 174(4)
    C20 H20B O13 4_675  .96 2.58 3.486(6) 158
