##############################################################################
###                                                                        ###
###        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 2.4.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
# 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     2010-06-04
_journal_date_accepted     2010-06-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     o1861
_journal_page_last     o1861
_journal_paper_category     QO
_journal_coeditor_code     ZQ2043
_publ_contact_author_name     'Qiao, Hong-Yun'
_publ_contact_author_address
;
Institute of Functional Biomolecules
State Key Laboratory of Pharmaceutical Biotechnology
Nanjing University
Nanjing 210093
People's Republic of China
;
_publ_contact_author_email     'qiaohy2010@gmail.com'
_publ_contact_author_fax     '0086-25-83593201'
_publ_contact_author_phone     '0086-25-83592085'
_publ_section_title
;
1-Diphenylmethyl-4-ethylpiperazine-1,4-diium dichloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Qiao, Hong-Yun'
;
Institute of Functional Biomolecules
State Key Laboratory of Pharmaceutical Biotechnology
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Xu, Su-Hai'
;
Institute of Functional Biomolecules
State Key Laboratory of Pharmaceutical Biotechnology
Nanjing University
Nanjing 210093
People's Republic of China
;
    'Jiang, He-Xia'
;
Department of General Surgery
Center of Minimally Invasive Surgery
the 81st Hospital of PLA
Nanjing 210002
People's Republic of China
;
_publ_section_synopsis     .
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Diphenylmethyl-4-ethylpiperazine-1,4-diium dichloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H26 N2 2+, 2(Cl -)'
_chemical_formula_sum     'C19 H26 Cl2 N2'
_chemical_formula_iupac     'C19 H26 N2 2+, 2Cl -'
_chemical_formula_weight     353.32
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     15.069(3)
_cell_length_b     7.2950(15)
_cell_length_c     18.565(4)
_cell_angle_alpha     90.00
_cell_angle_beta     106.35(3)
_cell_angle_gamma     90.00
_cell_volume     1958.3(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9
_cell_measurement_theta_max     12
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.198
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     752
_exptl_absorpt_coefficient_mu     0.333
_exptl_absorpt_correction_type     psi-scan
_exptl_absorpt_process_details     '(North <i>et al.</i>,  1968)'
_exptl_absorpt_correction_T_min     0.907
_exptl_absorpt_correction_T_max     0.968
_exptl_special_details
;
;
_diffrn_ambient_temperature     293(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     'Enraf--Nonius CAD-4'
_diffrn_measurement_method     '\w/2\q scan'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3684
_diffrn_reflns_av_R_equivalents     0.0280
_diffrn_reflns_av_sigmaI/netI     0.0681
_diffrn_reflns_theta_min     1.41
_diffrn_reflns_theta_max     25.27
_diffrn_reflns_theta_full     25.27
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     0
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     0
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -22
_diffrn_reflns_limit_l_max     21
_diffrn_standards_number     200
_diffrn_standards_interval_count     3
_diffrn_standards_interval_time     120
_diffrn_standards_decay_%     1
_refine_special_details
;
Refinement of <i>F</i>^2^ against ALL reflections. The weighted <i>R</i>-factor
<i>wR</i> and goodness of fit <i>S</i> are based on <i>F</i>^2^, conventional
<i>R</i>-factors <i>R</i> are based on <i>F</i>, with <i>F</i> set to zero for
negative <i>F</i>^2^. The threshold expression of <i>F</i>^2^ >
\s(<i>F</i>^2^) is used only for calculating <i>R</i>-factors(gt) <i>etc</i>.
and is not relevant to the choice of reflections for refinement.
<i>R</i>-factors based on <i>F</i>^2^ are statistically about twice as large
as those based on <i>F</i>, and <i>R</i>- factors based on ALL data will be
even larger.
;
_reflns_number_total     3542
_reflns_number_gt     2101
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1151
_refine_ls_R_factor_gt     0.0620
_refine_ls_wR_factor_gt     0.1321
_refine_ls_wR_factor_ref     0.1573
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.027
_refine_ls_number_reflns     3542
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.1129P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.381
_refine_diff_density_min     -0.248
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_cell_refinement     'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction     'XCAD4 (Harms & Wocadlo, 1995)'
_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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.6307(3) 0.4082(10) 0.0245(3) 0.0936(17) Uani d . 1 . .
    H H1A 0.6052 0.4038 -0.0273 0.112 Uiso calc R 1 . .
    C C2 0.6600(4) 0.2480(8) 0.0637(3) 0.0916(16) Uani d . 1 . .
    H H2A 0.6549 0.1369 0.0383 0.110 Uiso calc R 1 . .
    C C3 0.6968(3) 0.2534(6) 0.1407(2) 0.0710(13) Uani d . 1 . .
    H H3A 0.7158 0.1459 0.1676 0.085 Uiso calc R 1 . .
    C C4 0.7053(2) 0.4206(5) 0.17766(19) 0.0473(9) Uani d . 1 . .
    C C5 0.6766(3) 0.5794(6) 0.1372(2) 0.0576(10) Uani d . 1 . .
    H H5A 0.6830 0.6915 0.1619 0.069 Uiso calc R 1 . .
    C C6 0.6387(3) 0.5729(8) 0.0607(3) 0.0816(14) Uani d . 1 . .
    H H6A 0.6187 0.6799 0.0338 0.098 Uiso calc R 1 . .
    C C7 0.7408(2) 0.4406(4) 0.26239(18) 0.0404(8) Uani d . 1 . .
    H H7A 0.7627 0.5672 0.2719 0.049 Uiso calc R 1 . .
    C C8 0.6648(2) 0.4179(5) 0.30018(19) 0.0444(9) Uani d . 1 . .
    C C9 0.6408(3) 0.5678(5) 0.3367(2) 0.0572(10) Uani d . 1 . .
    H H9A 0.6747 0.6758 0.3413 0.069 Uiso calc R 1 . .
    C C10 0.5665(3) 0.5563(7) 0.3663(2) 0.0754(13) Uani d . 1 . .
    H H10A 0.5506 0.6578 0.3903 0.090 Uiso calc R 1 . .
    C C11 0.5164(3) 0.4010(8) 0.3610(2) 0.0766(14) Uani d . 1 . .
    H H11A 0.4664 0.3957 0.3810 0.092 Uiso calc R 1 . .
    C C12 0.5400(3) 0.2510(7) 0.3258(2) 0.0729(13) Uani d . 1 . .
    H H12A 0.5056 0.1437 0.3222 0.087 Uiso calc R 1 . .
    C C13 0.6142(3) 0.2571(6) 0.2956(2) 0.0606(11) Uani d . 1 . .
    H H13A 0.6300 0.1541 0.2724 0.073 Uiso calc R 1 . .
    C C14 0.9003(2) 0.3678(4) 0.26354(17) 0.0410(8) Uani d . 1 . .
    H H14A 0.9148 0.4970 0.2721 0.049 Uiso calc R 1 . .
    H H14B 0.8801 0.3476 0.2097 0.049 Uiso calc R 1 . .
    C C15 0.9859(2) 0.2566(5) 0.29714(17) 0.0432(9) Uani d . 1 . .
    H H15A 0.9727 0.1281 0.2854 0.052 Uiso calc R 1 . .
    H H15B 1.0342 0.2941 0.2751 0.052 Uiso calc R 1 . .
    C C16 0.9435(2) 0.2275(5) 0.41299(18) 0.0458(9) Uani d . 1 . .
    H H16A 0.9638 0.2468 0.4669 0.055 Uiso calc R 1 . .
    H H16B 0.9295 0.0983 0.4039 0.055 Uiso calc R 1 . .
    C C17 0.8575(2) 0.3387(5) 0.37957(17) 0.0464(9) Uani d . 1 . .
    H H17A 0.8093 0.2996 0.4015 0.056 Uiso calc R 1 . .
    H H17B 0.8705 0.4668 0.3921 0.056 Uiso calc R 1 . .
    C C18 1.1074(3) 0.1783(5) 0.4132(2) 0.0553(10) Uani d . 1 . .
    H H18A 1.1505 0.2061 0.3845 0.066 Uiso calc R 1 . .
    H H18B 1.0950 0.0476 0.4091 0.066 Uiso calc R 1 . .
    C C19 1.1516(3) 0.2259(6) 0.4946(2) 0.0720(13) Uani d . 1 . .
    H H19A 1.2073 0.1561 0.5132 0.108 Uiso calc R 1 . .
    H H19B 1.1095 0.1975 0.5234 0.108 Uiso calc R 1 . .
    H H19C 1.1660 0.3543 0.4989 0.108 Uiso calc R 1 . .
    Cl Cl1 1.05758(8) 0.68359(12) 0.40163(5) 0.0639(4) Uani d . 1 . .
    Cl Cl2 0.80657(8) -0.09301(13) 0.27873(7) 0.0756(4) Uani d . 1 . .
    H H1B 0.807(2) 0.193(5) 0.2866(18) 0.059(11) Uiso d . 1 . .
    H H2B 1.033(2) 0.392(5) 0.3885(19) 0.056(11) Uiso d . 1 . .
    N N1 0.82357(19) 0.3192(4) 0.29633(14) 0.0370(7) Uani d . 1 . .
    N N2 1.0189(2) 0.2800(4) 0.37993(15) 0.0401(7) Uani d . 1 . .
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
    C1 0.082(4) 0.141(5) 0.045(3) -0.003(4) -0.003(2) -0.009(3)
    C2 0.105(4) 0.097(4) 0.064(3) -0.014(3) 0.010(3) -0.028(3)
    C3 0.095(3) 0.062(3) 0.047(3) -0.010(3) 0.005(2) -0.012(2)
    C4 0.044(2) 0.054(2) 0.044(2) -0.0073(19) 0.0123(17) -0.0052(19)
    C5 0.057(3) 0.061(3) 0.052(2) 0.004(2) 0.011(2) 0.006(2)
    C6 0.078(3) 0.100(4) 0.059(3) 0.013(3) 0.007(3) 0.012(3)
    C7 0.049(2) 0.0257(17) 0.047(2) -0.0090(16) 0.0137(17) -0.0047(15)
    C8 0.044(2) 0.045(2) 0.044(2) -0.0045(18) 0.0120(17) -0.0011(17)
    C9 0.067(3) 0.053(2) 0.058(2) -0.001(2) 0.027(2) -0.0058(19)
    C10 0.081(3) 0.085(4) 0.071(3) 0.010(3) 0.039(3) -0.010(3)
    C11 0.062(3) 0.108(4) 0.064(3) -0.001(3) 0.026(2) 0.009(3)
    C12 0.060(3) 0.086(3) 0.076(3) -0.028(3) 0.024(2) 0.003(3)
    C13 0.064(3) 0.062(3) 0.057(2) -0.012(2) 0.019(2) -0.005(2)
    C14 0.051(2) 0.0358(19) 0.0404(19) -0.0036(17) 0.0191(17) -0.0005(15)
    C15 0.060(2) 0.0354(18) 0.0395(19) -0.0084(17) 0.0220(17) -0.0077(15)
    C16 0.061(2) 0.043(2) 0.0389(19) -0.0094(19) 0.0220(18) -0.0034(16)
    C17 0.055(2) 0.050(2) 0.039(2) -0.0078(19) 0.0220(17) -0.0059(17)
    C18 0.059(2) 0.040(2) 0.063(2) 0.008(2) 0.012(2) -0.0043(19)
    C19 0.068(3) 0.077(3) 0.064(3) 0.011(2) 0.005(2) -0.001(2)
    Cl1 0.1106(9) 0.0332(5) 0.0560(6) -0.0187(5) 0.0369(6) -0.0078(4)
    Cl2 0.0951(9) 0.0287(5) 0.0988(9) -0.0145(5) 0.0205(7) -0.0052(5)
    N1 0.0494(18) 0.0276(14) 0.0358(15) -0.0083(14) 0.0151(13) -0.0055(12)
    N2 0.0539(19) 0.0269(16) 0.0408(17) -0.0027(14) 0.0155(14) -0.0052(13)
_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
    C1 C6 . 1.366(7) ?
    C1 C2 . 1.382(7) ?
    C1 H1A . 0.9300 ?
    C2 C3 . 1.381(6) ?
    C2 H2A . 0.9300 ?
    C3 C4 . 1.388(5) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.382(5) ?
    C4 C7 . 1.519(4) ?
    C5 C6 . 1.373(5) ?
    C5 H5A . 0.9300 ?
    C6 H6A . 0.9300 ?
    C7 C8 . 1.512(5) ?
    C7 N1 . 1.514(4) ?
    C7 H7A . 0.9800 ?
    C8 C9 . 1.387(5) ?
    C8 C13 . 1.388(5) ?
    C9 C10 . 1.382(5) ?
    C9 H9A . 0.9300 ?
    C10 C11 . 1.350(6) ?
    C10 H10A . 0.9300 ?
    C11 C12 . 1.371(6) ?
    C11 H11A . 0.9300 ?
    C12 C13 . 1.386(5) ?
    C12 H12A . 0.9300 ?
    C13 H13A . 0.9300 ?
    C14 N1 . 1.493(4) ?
    C14 C15 . 1.502(4) ?
    C14 H14A . 0.9700 ?
    C14 H14B . 0.9700 ?
    C15 N2 . 1.486(4) ?
    C15 H15A . 0.9700 ?
    C15 H15B . 0.9700 ?
    C16 N2 . 1.486(4) ?
    C16 C17 . 1.506(5) ?
    C16 H16A . 0.9700 ?
    C16 H16B . 0.9700 ?
    C17 N1 . 1.492(4) ?
    C17 H17A . 0.9700 ?
    C17 H17B . 0.9700 ?
    C18 N2 . 1.499(4) ?
    C18 C19 . 1.510(5) ?
    C18 H18A . 0.9700 ?
    C18 H18B . 0.9700 ?
    C19 H19A . 0.9600 ?
    C19 H19B . 0.9600 ?
    C19 H19C . 0.9600 ?
    N1 H1B . 0.96(4) ?
    N2 H2B . 0.85(4) ?
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 C1 C2 . . 120.9(4) ?
    C6 C1 H1A . . 119.6 ?
    C2 C1 H1A . . 119.6 ?
    C3 C2 C1 . . 119.8(5) ?
    C3 C2 H2A . . 120.1 ?
    C1 C2 H2A . . 120.1 ?
    C2 C3 C4 . . 119.4(4) ?
    C2 C3 H3A . . 120.3 ?
    C4 C3 H3A . . 120.3 ?
    C5 C4 C3 . . 119.8(3) ?
    C5 C4 C7 . . 116.6(3) ?
    C3 C4 C7 . . 123.5(3) ?
    C6 C5 C4 . . 120.6(4) ?
    C6 C5 H5A . . 119.7 ?
    C4 C5 H5A . . 119.7 ?
    C1 C6 C5 . . 119.5(5) ?
    C1 C6 H6A . . 120.2 ?
    C5 C6 H6A . . 120.2 ?
    C8 C7 N1 . . 112.7(3) ?
    C8 C7 C4 . . 112.2(3) ?
    N1 C7 C4 . . 112.6(3) ?
    C8 C7 H7A . . 106.3 ?
    N1 C7 H7A . . 106.3 ?
    C4 C7 H7A . . 106.3 ?
    C9 C8 C13 . . 118.8(3) ?
    C9 C8 C7 . . 118.4(3) ?
    C13 C8 C7 . . 122.6(3) ?
    C10 C9 C8 . . 119.9(4) ?
    C10 C9 H9A . . 120.1 ?
    C8 C9 H9A . . 120.1 ?
    C11 C10 C9 . . 121.4(4) ?
    C11 C10 H10A . . 119.3 ?
    C9 C10 H10A . . 119.3 ?
    C10 C11 C12 . . 119.4(4) ?
    C10 C11 H11A . . 120.3 ?
    C12 C11 H11A . . 120.3 ?
    C11 C12 C13 . . 120.9(4) ?
    C11 C12 H12A . . 119.5 ?
    C13 C12 H12A . . 119.5 ?
    C12 C13 C8 . . 119.6(4) ?
    C12 C13 H13A . . 120.2 ?
    C8 C13 H13A . . 120.2 ?
    N1 C14 C15 . . 112.0(3) ?
    N1 C14 H14A . . 109.2 ?
    C15 C14 H14A . . 109.2 ?
    N1 C14 H14B . . 109.2 ?
    C15 C14 H14B . . 109.2 ?
    H14A C14 H14B . . 107.9 ?
    N2 C15 C14 . . 111.4(3) ?
    N2 C15 H15A . . 109.3 ?
    C14 C15 H15A . . 109.3 ?
    N2 C15 H15B . . 109.3 ?
    C14 C15 H15B . . 109.3 ?
    H15A C15 H15B . . 108.0 ?
    N2 C16 C17 . . 111.1(3) ?
    N2 C16 H16A . . 109.4 ?
    C17 C16 H16A . . 109.4 ?
    N2 C16 H16B . . 109.4 ?
    C17 C16 H16B . . 109.4 ?
    H16A C16 H16B . . 108.0 ?
    N1 C17 C16 . . 112.3(3) ?
    N1 C17 H17A . . 109.1 ?
    C16 C17 H17A . . 109.1 ?
    N1 C17 H17B . . 109.1 ?
    C16 C17 H17B . . 109.1 ?
    H17A C17 H17B . . 107.9 ?
    N2 C18 C19 . . 112.9(3) ?
    N2 C18 H18A . . 109.0 ?
    C19 C18 H18A . . 109.0 ?
    N2 C18 H18B . . 109.0 ?
    C19 C18 H18B . . 109.0 ?
    H18A C18 H18B . . 107.8 ?
    C18 C19 H19A . . 109.5 ?
    C18 C19 H19B . . 109.5 ?
    H19A C19 H19B . . 109.5 ?
    C18 C19 H19C . . 109.5 ?
    H19A C19 H19C . . 109.5 ?
    H19B C19 H19C . . 109.5 ?
    C17 N1 C14 . . 108.7(3) ?
    C17 N1 C7 . . 112.2(3) ?
    C14 N1 C7 . . 109.4(2) ?
    C17 N1 H1B . . 106(2) ?
    C14 N1 H1B . . 110(2) ?
    C7 N1 H1B . . 110(2) ?
    C16 N2 C15 . . 109.0(3) ?
    C16 N2 C18 . . 113.4(3) ?
    C15 N2 C18 . . 111.7(3) ?
    C16 N2 H2B . . 111(2) ?
    C15 N2 H2B . . 107(2) ?
    C18 N2 H2B . . 104(2) ?
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
    C6 C1 C2 C3 . . . . 0.9(8) ?
    C1 C2 C3 C4 . . . . -1.0(8) ?
    C2 C3 C4 C5 . . . . 0.2(6) ?
    C2 C3 C4 C7 . . . . 177.2(4) ?
    C3 C4 C5 C6 . . . . 0.8(6) ?
    C7 C4 C5 C6 . . . . -176.4(4) ?
    C2 C1 C6 C5 . . . . 0.1(8) ?
    C4 C5 C6 C1 . . . . -0.9(7) ?
    C5 C4 C7 C8 . . . . 90.9(4) ?
    C3 C4 C7 C8 . . . . -86.2(4) ?
    C5 C4 C7 N1 . . . . -140.7(3) ?
    C3 C4 C7 N1 . . . . 42.2(5) ?
    N1 C7 C8 C9 . . . . 117.2(4) ?
    C4 C7 C8 C9 . . . . -114.5(4) ?
    N1 C7 C8 C13 . . . . -67.0(4) ?
    C4 C7 C8 C13 . . . . 61.3(4) ?
    C13 C8 C9 C10 . . . . -1.4(6) ?
    C7 C8 C9 C10 . . . . 174.5(3) ?
    C8 C9 C10 C11 . . . . 0.5(7) ?
    C9 C10 C11 C12 . . . . 0.3(7) ?
    C10 C11 C12 C13 . . . . -0.1(7) ?
    C11 C12 C13 C8 . . . . -0.8(6) ?
    C9 C8 C13 C12 . . . . 1.5(6) ?
    C7 C8 C13 C12 . . . . -174.2(3) ?
    N1 C14 C15 N2 . . . . -57.9(4) ?
    N2 C16 C17 N1 . . . . 57.7(4) ?
    C16 C17 N1 C14 . . . . -55.1(4) ?
    C16 C17 N1 C7 . . . . -176.3(3) ?
    C15 C14 N1 C17 . . . . 55.1(3) ?
    C15 C14 N1 C7 . . . . 177.9(2) ?
    C8 C7 N1 C17 . . . . -51.4(3) ?
    C4 C7 N1 C17 . . . . -179.6(3) ?
    C8 C7 N1 C14 . . . . -172.2(3) ?
    C4 C7 N1 C14 . . . . 59.7(3) ?
    C17 C16 N2 C15 . . . . -57.0(4) ?
    C17 C16 N2 C18 . . . . 177.9(3) ?
    C14 C15 N2 C16 . . . . 57.4(3) ?
    C14 C15 N2 C18 . . . . -176.6(3) ?
    C19 C18 N2 C16 . . . . -66.6(4) ?
    C19 C18 N2 C15 . . . . 169.8(3) ?
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 H1B Cl2 . 0.96(4) 2.09(4) 3.028(3) 165(3)
    N2 H2B Cl1 . 0.85(4) 2.16(4) 3.006(3) 174(3)