##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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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#                                                                            #
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data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-06-20
_journal_date_accepted     2010-06-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1833
_journal_page_last     o1834
_journal_paper_category     QO
_journal_coeditor_code     RK2214
_publ_contact_author_name     'Dr. Md. Alamgir Hossain'
_publ_contact_author_address
;
Department of Chemistry
1400 J. R. Lynch St.
P.O. Box 17910
Jackson State University
Jackson, MS 39217-0510  USA
;
_publ_contact_author_email     alamgir@chem.jsums.edu
_publ_contact_author_fax     '601 979 3674'
_publ_contact_author_phone     '601 979 3748'
_publ_section_title
;
Tris(2-benzamidoethyl)ammonium tetrafluoroborate
;
loop_
    _publ_author_name
    _publ_author_address
    'Pilate, Marcy L.'
;
Department of Chemistry and Biochemistry
Jackson State University
Jackson, MS 39217, USA
;
    'Blount, Henry'
;
Department of Chemistry and Biochemistry
Jackson State University
Jackson, MS 39217, USA
;
    'Fronczek, Frank R. '
;
Department of Chemistry
Louisiana State University
Baton Rouge, LA 70803, USA
;
    'Hossain, Md. Alamgir'
;
Department of Chemistry and Biochemistry
Jackson State University
Jackson, MS 39217, USA
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
Tris(2-benzamidoethyl)ammonium tetrafluoroborate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H31 N4 O3 +, B F4 -'
_chemical_formula_sum     'C27 H31 B F4 N4 O3'
_chemical_formula_iupac     'C27 H31 N4 O3 +, B F4 -'
_chemical_formula_weight     546.37
_chemical_melting_point     423
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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     13.325(2)
_cell_length_b     9.572(2)
_cell_length_c     21.118(3)
_cell_angle_alpha     90
_cell_angle_beta     94.546(10)
_cell_angle_gamma     90
_cell_volume     2685.1(8)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     6170
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     27.1
_cell_measurement_temperature     90.0(5)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.27
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.352
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1144
_exptl_absorpt_coefficient_mu     0.107
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
;
_diffrn_ambient_temperature     90.0(5)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine--focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device
                         'Nonius KappaCCD diffractometer with Oxford Cryostream'
_diffrn_measurement_method     ' ω--scans with κ--offsets'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     31844
_diffrn_reflns_av_R_equivalents     0.068
_diffrn_reflns_av_sigmaI/netI     0.0920
_diffrn_reflns_theta_min     2.6
_diffrn_reflns_theta_max     27.1
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -17
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     26
_diffrn_standards_number     ?
_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     5914
_reflns_number_gt     3310
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.117
_refine_ls_R_factor_gt     0.048
_refine_ls_wR_factor_gt     0.093
_refine_ls_wR_factor_ref     0.114
_refine_ls_goodness_of_fit_ref     0.996
_refine_ls_restrained_S_all     0.996
_refine_ls_number_reflns     5914
_refine_ls_number_parameters     365
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0492P)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     0.256
_refine_diff_density_min     -0.266
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.0047(7)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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'
    'B' 'B' 0.0013 0.0007
                         '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'
    '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     'COLLECT (Nonius, 1999)'
_computing_cell_refinement
;
DENZO and SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_reduction
                  'DENZO and SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     'SHELXL97 (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_disorder_assembly
    _atom_site_disorder_group
    O O1 0.69598(10) 0.66708(15) 0.51248(6) 0.0235(3) Uani d . 1 . .
    O O2 0.97004(10) 0.65535(14) 0.51217(6) 0.0237(3) Uani d . 1 . .
    O O3 0.66033(11) 0.35955(15) 0.42976(6) 0.0269(4) Uani d . 1 . .
    N N1 0.77743(12) 0.52786(18) 0.61191(7) 0.0190(4) Uani d . 1 . .
    H H1N 0.7663(14) 0.584(2) 0.5718(9) 0.023 Uiso d . 1 . .
    N N2 0.55317(13) 0.65036(19) 0.56356(7) 0.0227(4) Uani d . 1 . .
    H H2N 0.4881(16) 0.655(2) 0.5611(9) 0.027 Uiso d . 1 . .
    N N3 0.89693(13) 0.78188(18) 0.58685(7) 0.0207(4) Uani d . 1 . .
    H H3N 0.8721(15) 0.867(2) 0.5972(9) 0.025 Uiso d . 1 . .
    N N4 0.81500(13) 0.39353(18) 0.47972(7) 0.0204(4) Uani d . 1 . .
    H H4N 0.8780(16) 0.412(2) 0.4753(9) 0.024 Uiso d . 1 . .
    C C1 0.67293(15) 0.4962(2) 0.63108(9) 0.0212(5) Uani d . 1 . .
    H H1A 0.6782 0.4611 0.6753 0.025 Uiso calc R 1 . .
    H H1B 0.6432 0.4208 0.6035 0.025 Uiso calc R 1 . .
    C C2 0.60230(16) 0.6219(2) 0.62667(8) 0.0238(5) Uani d . 1 . .
    H H2A 0.5495 0.6073 0.6564 0.029 Uiso calc R 1 . .
    H H2B 0.6412 0.7058 0.6411 0.029 Uiso calc R 1 . .
    C C3 0.60327(16) 0.6812(2) 0.51281(9) 0.0208(5) Uani d . 1 . .
    C C4 0.54443(15) 0.7377(2) 0.45532(9) 0.0203(5) Uani d . 1 . .
    C C5 0.46519(16) 0.8306(2) 0.45962(9) 0.0243(5) Uani d . 1 . .
    H H5 0.4442 0.8555 0.5001 0.029 Uiso calc R 1 . .
    C C6 0.41677(16) 0.8870(2) 0.40503(10) 0.0293(5) Uani d . 1 . .
    H H6 0.3632 0.9516 0.4081 0.035 Uiso calc R 1 . .
    C C7 0.44618(16) 0.8496(2) 0.34635(10) 0.0310(6) Uani d . 1 . .
    H H7 0.4121 0.8875 0.3090 0.037 Uiso calc R 1 . .
    C C8 0.52504(17) 0.7572(2) 0.34138(10) 0.0312(6) Uani d . 1 . .
    H H8 0.5447 0.7313 0.3008 0.037 Uiso calc R 1 . .
    C C9 0.57503(16) 0.7029(2) 0.39571(9) 0.0269(5) Uani d . 1 . .
    H H9 0.6305 0.6417 0.3924 0.032 Uiso calc R 1 . .
    C C10 0.83608(15) 0.6116(2) 0.66272(9) 0.0218(5) Uani d . 1 . .
    H H10A 0.8600 0.5483 0.6978 0.026 Uiso calc R 1 . .
    H H10B 0.7908 0.6814 0.6801 0.026 Uiso calc R 1 . .
    C C11 0.92603(15) 0.6867(2) 0.63859(9) 0.0224(5) Uani d . 1 . .
    H H11A 0.9612 0.7398 0.6740 0.027 Uiso calc R 1 . .
    H H11B 0.9737 0.6168 0.6239 0.027 Uiso calc R 1 . .
    C C12 0.92266(15) 0.7599(2) 0.52720(9) 0.0197(5) Uani d . 1 . .
    C C13 0.88929(15) 0.8684(2) 0.47918(9) 0.0191(5) Uani d . 1 . .
    C C14 0.80176(16) 0.9456(2) 0.48281(9) 0.0237(5) Uani d . 1 . .
    H H14 0.7618 0.9325 0.5176 0.028 Uiso calc R 1 . .
    C C15 0.77232(17) 1.0423(2) 0.43572(9) 0.0270(5) Uani d . 1 . .
    H H15 0.7120 1.0942 0.4382 0.032 Uiso calc R 1 . .
    C C16 0.83094(17) 1.0627(2) 0.38534(9) 0.0267(5) Uani d . 1 . .
    H H16 0.8112 1.1296 0.3535 0.032 Uiso calc R 1 . .
    C C17 0.91824(17) 0.9861(2) 0.38106(9) 0.0272(5) Uani d . 1 . .
    H H17 0.9583 1.0000 0.3463 0.033 Uiso calc R 1 . .
    C C18 0.94687(16) 0.8890(2) 0.42784(9) 0.0231(5) Uani d . 1 . .
    H H18 1.0065 0.8359 0.4248 0.028 Uiso calc R 1 . .
    C C19 0.83279(16) 0.3959(2) 0.59740(8) 0.0211(5) Uani d . 1 . .
    H H19A 0.8299 0.3309 0.6337 0.025 Uiso calc R 1 . .
    H H19B 0.9045 0.4192 0.5935 0.025 Uiso calc R 1 . .
    C C20 0.79230(16) 0.3222(2) 0.53764(8) 0.0223(5) Uani d . 1 . .
    H H20A 0.8210 0.2268 0.5374 0.027 Uiso calc R 1 . .
    H H20B 0.7184 0.3131 0.5381 0.027 Uiso calc R 1 . .
    C C21 0.74826(15) 0.4008(2) 0.42910(9) 0.0199(5) Uani d . 1 . .
    C C22 0.78649(15) 0.4566(2) 0.36920(9) 0.0211(5) Uani d . 1 . .
    C C23 0.86024(15) 0.5588(2) 0.36906(9) 0.0228(5) Uani d . 1 . .
    H H23 0.8870 0.5989 0.4080 0.027 Uiso calc R 1 . .
    C C24 0.89490(16) 0.6025(2) 0.31219(9) 0.0280(5) Uani d . 1 . .
    H H24 0.9440 0.6746 0.3122 0.034 Uiso calc R 1 . .
    C C25 0.85853(18) 0.5420(2) 0.25530(9) 0.0308(6) Uani d . 1 . .
    H H25 0.8844 0.5699 0.2166 0.037 Uiso calc R 1 . .
    C C26 0.78424(18) 0.4403(2) 0.25513(10) 0.0338(6) Uani d . 1 . .
    H H26 0.7589 0.3986 0.2163 0.041 Uiso calc R 1 . .
    C C27 0.74720(17) 0.4001(2) 0.31173(9) 0.0274(5) Uani d . 1 . .
    H H27 0.6945 0.3332 0.3114 0.033 Uiso calc R 1 . .
    B B1 0.8258(2) 1.0373(3) 0.69733(11) 0.0262(6) Uani d . 1 . .
    F F1 0.74417(10) 0.95062(13) 0.70473(5) 0.0393(4) Uani d . 1 . .
    F F2 0.81014(10) 1.16644(13) 0.72363(5) 0.0396(4) Uani d . 1 . .
    F F3 0.83701(9) 1.05339(12) 0.63193(5) 0.0297(3) Uani d . 1 . .
    F F4 0.91193(10) 0.97574(15) 0.72626(5) 0.0444(4) Uani d . 1 . .
_geom_special_details
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix. The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry. An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'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 C3 . 1.243(2) ?
    O2 C12 . 1.238(2) ?
    O3 C21 . 1.238(2) ?
    N1 C19 . 1.506(2) ?
    N1 C10 . 1.507(2) ?
    N1 C1 . 1.511(2) ?
    N1 H1N . 1.003(19) ?
    N2 C3 . 1.340(2) ?
    N2 C2 . 1.463(2) ?
    N2 H2N . 0.87(2) ?
    N3 C12 . 1.348(2) ?
    N3 C11 . 1.452(2) ?
    N3 H3N . 0.92(2) ?
    N4 C21 . 1.337(2) ?
    N4 C20 . 1.453(2) ?
    N4 H4N . 0.87(2) ?
    C1 C2 . 1.526(3) ?
    C1 H1A . 0.9900 ?
    C1 H1B . 0.9900 ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 C4 . 1.493(3) ?
    C4 C5 . 1.389(3) ?
    C4 C9 . 1.394(3) ?
    C5 C6 . 1.385(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.376(3) ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.384(3) ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.382(3) ?
    C8 H8 . 0.9500 ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.520(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.495(3) ?
    C13 C14 . 1.388(3) ?
    C13 C18 . 1.391(3) ?
    C14 C15 . 1.392(3) ?
    C14 H14 . 0.9500 ?
    C15 C16 . 1.383(3) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.384(3) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.388(3) ?
    C17 H17 . 0.9500 ?
    C18 H18 . 0.9500 ?
    C19 C20 . 1.508(3) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C21 C22 . 1.499(3) ?
    C22 C23 . 1.387(3) ?
    C22 C27 . 1.392(3) ?
    C23 C24 . 1.385(3) ?
    C23 H23 . 0.9500 ?
    C24 C25 . 1.386(3) ?
    C24 H24 . 0.9500 ?
    C25 C26 . 1.388(3) ?
    C25 H25 . 0.9500 ?
    C26 C27 . 1.384(3) ?
    C26 H26 . 0.9500 ?
    C27 H27 . 0.9500 ?
    B1 F2 . 1.378(3) ?
    B1 F1 . 1.387(3) ?
    B1 F4 . 1.388(3) ?
    B1 F3 . 1.409(2) ?
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
    C19 N1 C10 . . 110.86(15) ?
    C19 N1 C1 . . 111.27(16) ?
    C10 N1 C1 . . 110.66(15) ?
    C19 N1 H1N . . 108.6(11) ?
    C10 N1 H1N . . 110.5(11) ?
    C1 N1 H1N . . 104.8(11) ?
    C3 N2 C2 . . 123.66(18) ?
    C3 N2 H2N . . 120.1(13) ?
    C2 N2 H2N . . 115.9(13) ?
    C12 N3 C11 . . 122.19(18) ?
    C12 N3 H3N . . 119.1(12) ?
    C11 N3 H3N . . 117.5(12) ?
    C21 N4 C20 . . 121.86(18) ?
    C21 N4 H4N . . 119.3(13) ?
    C20 N4 H4N . . 116.9(13) ?
    N1 C1 C2 . . 113.71(17) ?
    N1 C1 H1A . . 108.8 ?
    C2 C1 H1A . . 108.8 ?
    N1 C1 H1B . . 108.8 ?
    C2 C1 H1B . . 108.8 ?
    H1A C1 H1B . . 107.7 ?
    N2 C2 C1 . . 115.56(16) ?
    N2 C2 H2A . . 108.4 ?
    C1 C2 H2A . . 108.4 ?
    N2 C2 H2B . . 108.4 ?
    C1 C2 H2B . . 108.4 ?
    H2A C2 H2B . . 107.5 ?
    O1 C3 N2 . . 122.62(18) ?
    O1 C3 C4 . . 119.51(17) ?
    N2 C3 C4 . . 117.86(18) ?
    C5 C4 C9 . . 119.34(18) ?
    C5 C4 C3 . . 122.10(17) ?
    C9 C4 C3 . . 118.41(19) ?
    C6 C5 C4 . . 120.12(19) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C7 C6 C5 . . 120.0(2) ?
    C7 C6 H6 . . 120.0 ?
    C5 C6 H6 . . 120.0 ?
    C6 C7 C8 . . 120.5(2) ?
    C6 C7 H7 . . 119.8 ?
    C8 C7 H7 . . 119.8 ?
    C9 C8 C7 . . 119.8(2) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C8 C9 C4 . . 120.3(2) ?
    C8 C9 H9 . . 119.9 ?
    C4 C9 H9 . . 119.9 ?
    N1 C10 C11 . . 113.03(15) ?
    N1 C10 H10A . . 109.0 ?
    C11 C10 H10A . . 109.0 ?
    N1 C10 H10B . . 109.0 ?
    C11 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    N3 C11 C10 . . 112.24(16) ?
    N3 C11 H11A . . 109.2 ?
    C10 C11 H11A . . 109.2 ?
    N3 C11 H11B . . 109.2 ?
    C10 C11 H11B . . 109.2 ?
    H11A C11 H11B . . 107.9 ?
    O2 C12 N3 . . 122.60(18) ?
    O2 C12 C13 . . 121.20(17) ?
    N3 C12 C13 . . 116.19(18) ?
    C14 C13 C18 . . 119.04(19) ?
    C14 C13 C12 . . 122.60(17) ?
    C18 C13 C12 . . 118.33(18) ?
    C13 C14 C15 . . 120.34(19) ?
    C13 C14 H14 . . 119.8 ?
    C15 C14 H14 . . 119.8 ?
    C16 C15 C14 . . 119.9(2) ?
    C16 C15 H15 . . 120.0 ?
    C14 C15 H15 . . 120.0 ?
    C15 C16 C17 . . 120.3(2) ?
    C15 C16 H16 . . 119.9 ?
    C17 C16 H16 . . 119.9 ?
    C16 C17 C18 . . 119.6(2) ?
    C16 C17 H17 . . 120.2 ?
    C18 C17 H17 . . 120.2 ?
    C17 C18 C13 . . 120.8(2) ?
    C17 C18 H18 . . 119.6 ?
    C13 C18 H18 . . 119.6 ?
    N1 C19 C20 . . 114.47(16) ?
    N1 C19 H19A . . 108.6 ?
    C20 C19 H19A . . 108.6 ?
    N1 C19 H19B . . 108.6 ?
    C20 C19 H19B . . 108.6 ?
    H19A C19 H19B . . 107.6 ?
    N4 C20 C19 . . 113.57(17) ?
    N4 C20 H20A . . 108.9 ?
    C19 C20 H20A . . 108.9 ?
    N4 C20 H20B . . 108.9 ?
    C19 C20 H20B . . 108.9 ?
    H20A C20 H20B . . 107.7 ?
    O3 C21 N4 . . 122.99(18) ?
    O3 C21 C22 . . 120.58(17) ?
    N4 C21 C22 . . 116.38(18) ?
    C23 C22 C27 . . 119.33(19) ?
    C23 C22 C21 . . 122.77(17) ?
    C27 C22 C21 . . 117.88(19) ?
    C24 C23 C22 . . 119.99(19) ?
    C24 C23 H23 . . 120.0 ?
    C22 C23 H23 . . 120.0 ?
    C23 C24 C25 . . 120.5(2) ?
    C23 C24 H24 . . 119.8 ?
    C25 C24 H24 . . 119.8 ?
    C24 C25 C26 . . 119.7(2) ?
    C24 C25 H25 . . 120.1 ?
    C26 C25 H25 . . 120.1 ?
    C27 C26 C25 . . 119.7(2) ?
    C27 C26 H26 . . 120.1 ?
    C25 C26 H26 . . 120.1 ?
    C26 C27 C22 . . 120.6(2) ?
    C26 C27 H27 . . 119.7 ?
    C22 C27 H27 . . 119.7 ?
    F2 B1 F1 . . 110.24(19) ?
    F2 B1 F4 . . 110.49(19) ?
    F1 B1 F4 . . 108.96(19) ?
    F2 B1 F3 . . 109.16(19) ?
    F1 B1 F3 . . 108.70(18) ?
    F4 B1 F3 . . 109.26(18) ?
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
    C19 N1 C1 C2 . . . . -162.24(15) ?
    C10 N1 C1 C2 . . . . 74.0(2) ?
    C3 N2 C2 C1 . . . . -61.3(3) ?
    N1 C1 C2 N2 . . . . 83.1(2) ?
    C2 N2 C3 O1 . . . . 11.6(3) ?
    C2 N2 C3 C4 . . . . -167.04(19) ?
    O1 C3 C4 C5 . . . . -140.5(2) ?
    N2 C3 C4 C5 . . . . 38.1(3) ?
    O1 C3 C4 C9 . . . . 35.0(3) ?
    N2 C3 C4 C9 . . . . -146.4(2) ?
    C9 C4 C5 C6 . . . . 0.5(3) ?
    C3 C4 C5 C6 . . . . 175.96(19) ?
    C4 C5 C6 C7 . . . . 0.9(3) ?
    C5 C6 C7 C8 . . . . -1.0(3) ?
    C6 C7 C8 C9 . . . . -0.4(4) ?
    C7 C8 C9 C4 . . . . 1.9(3) ?
    C5 C4 C9 C8 . . . . -1.9(3) ?
    C3 C4 C9 C8 . . . . -177.53(19) ?
    C19 N1 C10 C11 . . . . 75.0(2) ?
    C1 N1 C10 C11 . . . . -161.06(17) ?
    C12 N3 C11 C10 . . . . -112.8(2) ?
    N1 C10 C11 N3 . . . . 58.7(2) ?
    C11 N3 C12 O2 . . . . 2.2(3) ?
    C11 N3 C12 C13 . . . . -178.72(17) ?
    O2 C12 C13 C14 . . . . 148.4(2) ?
    N3 C12 C13 C14 . . . . -30.7(3) ?
    O2 C12 C13 C18 . . . . -29.5(3) ?
    N3 C12 C13 C18 . . . . 151.42(18) ?
    C18 C13 C14 C15 . . . . -0.1(3) ?
    C12 C13 C14 C15 . . . . -177.89(18) ?
    C13 C14 C15 C16 . . . . -0.7(3) ?
    C14 C15 C16 C17 . . . . 0.8(3) ?
    C15 C16 C17 C18 . . . . -0.3(3) ?
    C16 C17 C18 C13 . . . . -0.5(3) ?
    C14 C13 C18 C17 . . . . 0.6(3) ?
    C12 C13 C18 C17 . . . . 178.56(18) ?
    C10 N1 C19 C20 . . . . -166.83(16) ?
    C1 N1 C19 C20 . . . . 69.6(2) ?
    C21 N4 C20 C19 . . . . -140.97(19) ?
    N1 C19 C20 N4 . . . . 72.5(2) ?
    C20 N4 C21 O3 . . . . 6.9(3) ?
    C20 N4 C21 C22 . . . . -170.42(17) ?
    O3 C21 C22 C23 . . . . 149.1(2) ?
    N4 C21 C22 C23 . . . . -33.5(3) ?
    O3 C21 C22 C27 . . . . -32.3(3) ?
    N4 C21 C22 C27 . . . . 145.04(19) ?
    C27 C22 C23 C24 . . . . -0.8(3) ?
    C21 C22 C23 C24 . . . . 177.74(19) ?
    C22 C23 C24 C25 . . . . -1.9(3) ?
    C23 C24 C25 C26 . . . . 2.3(3) ?
    C24 C25 C26 C27 . . . . -0.1(3) ?
    C25 C26 C27 C22 . . . . -2.5(3) ?
    C23 C22 C27 C26 . . . . 3.0(3) ?
    C21 C22 C27 C26 . . . . -175.61(19) ?
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
    N1 H1N O1 . 1.003(19) 1.70(2) 2.646(2) 155.2(16)
    N2 H2N O3 3_666 0.87(2) 2.01(2) 2.861(2) 168.8(19)
    N3 H3N F3 . 0.92(2) 2.00(2) 2.901(2) 170.0(18)
    N4 H4N O2 3_766 0.87(2) 2.12(2) 2.894(2) 147.5(19)
