##############################################################################
###                                                                        ###
###        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     ?
_journal_date_recd_electronic     2008-07-08
_journal_date_accepted     2008-07-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      8
_journal_page_first     o1505
_journal_page_last     o1505
_journal_paper_category     QO
_journal_coeditor_code     HK2490
_publ_contact_author
;
Muhammad Nawaz Tahir
University of Sargodha
Department of Physics
Sarodha
Pakistan
;
_publ_contact_author_email     dmntahir_uos@yahoo.com
_publ_contact_author_fax     '0092 48 32 22 121'
_publ_contact_author_phone     '0092 48 92 30 170'
_publ_section_title
;
3-(2-Benzamidophenyl)-4-(4-hydroxyphenyl)-5-methyl-4H-1,2,4-triazol-1-ium
chloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Arfan, Mohammad'
;
Institute of Chemical Sciences,
University of Peshawar,
Peshawar
Pakistan
;
    'Tahir, M. Nawaz'
;
Department of Physics,
University of Sargodha,
Sargodha
Pakistan
;
    'Khan, Rasool'
;
Institute of Chemical Sciences,
University of Peshawar,
Peshawar
Pakistan
;
    'Iqbal, Mohammad S.'
;
Department of Chemistry,
Government College University,
Lahore
Pakistan
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
3-(2-Benzamidophenyl)-4-(4-hydroxyphenyl)-5-methyl-4H-1,2,4-
triazol-1-ium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C22 H19 N4 O2 +, Cl -'
_chemical_formula_sum     'C22 H19 Cl N4 O2'
_chemical_formula_iupac     'C22 H19 N4 O2 +, Cl -'
_chemical_formula_weight     406.86
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P c a 21'
_symmetry_space_group_name_Hall     'P 2c -2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x,-y, z+1/2'
    '-x+1/2, y, z+1/2'
    'x+1/2, -y, z'
_cell_length_a     17.1336(15)
_cell_length_b     9.8967(9)
_cell_length_c     12.1910(10)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2067.2(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2009
_cell_measurement_theta_min     2.06
_cell_measurement_theta_max     28.80
_cell_measurement_temperature     296(2)
_exptl_crystal_description     prismatic
_exptl_crystal_colour     black
_exptl_crystal_size_max     0.25
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.307
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     848
_exptl_absorpt_coefficient_mu     0.210
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min     0.950
_exptl_absorpt_correction_T_max     0.960
_exptl_special_details
;
;
_diffrn_ambient_temperature     296(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 Kappa APEXII CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     7.40
_diffrn_reflns_number     13329
_diffrn_reflns_av_R_equivalents     0.0220
_diffrn_reflns_av_sigmaI/netI     0.0186
_diffrn_reflns_theta_min     2.06
_diffrn_reflns_theta_max     28.80
_diffrn_reflns_theta_full     28.80
_diffrn_measured_fraction_theta_max     0.994
_diffrn_measured_fraction_theta_full     0.994
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     18
_diffrn_reflns_limit_k_min     -13
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     12
_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     2809
_reflns_number_gt     2480
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0413
_refine_ls_R_factor_gt     0.0343
_refine_ls_wR_factor_gt     0.0918
_refine_ls_wR_factor_ref     0.0973
_refine_ls_goodness_of_fit_ref     1.019
_refine_ls_restrained_S_all     1.019
_refine_ls_number_reflns     2809
_refine_ls_number_parameters     272
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0606P)²+0.2556P] 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     0.197
_refine_diff_density_min     -0.206
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
_refine_ls_abs_structure_details     'Flack (1983) with no Friedel pairs'
_refine_ls_abs_structure_Flack     0.06(7)
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'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'APEX2 (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
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_thermal_displace_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    Cl Cl 0.18901(3) 0.41678(5) 0.23611(6) 0.0441(2) Uani . . 1.000
    O O1 0.08185(11) 0.8416(2) 0.61956(15) 0.0523(6) Uani . . 1.000
    O O2 0.23156(16) 1.1272(2) 0.1626(2) 0.0698(9) Uani . . 1.000
    N N1 -0.02194(12) 0.7017(2) 0.62595(16) 0.0396(6) Uani . . 1.000
    N N2 0.12701(11) 0.54036(19) 0.55257(17) 0.0394(5) Uani . . 1.000
    N N3 0.20680(12) 0.5419(2) 0.55843(18) 0.0410(6) Uani . . 1.000
    N N4 0.17842(10) 0.69261(19) 0.44104(16) 0.0345(5) Uani . . 1.000
    C C1 0.02424(13) 0.8077(2) 0.79409(19) 0.0364(6) Uani . . 1.000
    C C2 -0.01415(15) 0.7183(3) 0.8629(2) 0.0451(8) Uani . . 1.000
    C C3 -0.02023(18) 0.7468(4) 0.9741(2) 0.0583(10) Uani . . 1.000
    C C4 0.0117(2) 0.8628(3) 1.0166(3) 0.0640(10) Uani . . 1.000
    C C5 0.0506(2) 0.9501(3) 0.9485(3) 0.0648(10) Uani . . 1.000
    C C6 0.05751(18) 0.9231(3) 0.8372(2) 0.0513(8) Uani . . 1.000
    C C7 0.03122(13) 0.7860(2) 0.6732(2) 0.0364(6) Uani . . 1.000
    C C8 -0.03057(13) 0.6865(2) 0.51128(19) 0.0357(6) Uani . . 1.000
    C C9 -0.10597(14) 0.6966(3) 0.4680(2) 0.0477(8) Uani . . 1.000
    C C10 -0.11851(17) 0.6838(3) 0.3569(3) 0.0580(9) Uani . . 1.000
    C C11 -0.05706(19) 0.6642(3) 0.2866(2) 0.0590(10) Uani . . 1.000
    C C12 0.01801(16) 0.6538(3) 0.3276(2) 0.0476(8) Uani . . 1.000
    C C13 0.03172(13) 0.6628(2) 0.44022(18) 0.0352(6) Uani . . 1.000
    C C14 0.11081(12) 0.6336(2) 0.48077(18) 0.0340(6) Uani . . 1.000
    C C15 0.23791(13) 0.6310(2) 0.4926(2) 0.0391(6) Uani . . 1.000
    C C16 0.32228(14) 0.6578(3) 0.4792(3) 0.0637(10) Uani . . 1.000
    C C17 0.18724(12) 0.8055(2) 0.36715(19) 0.0348(6) Uani . . 1.000
    C C18 0.16505(16) 0.9329(2) 0.3999(2) 0.0441(7) Uani . . 1.000
    C C19 0.17852(16) 1.0418(3) 0.3320(2) 0.0497(8) Uani . . 1.000
    C C20 0.21503(14) 1.0236(2) 0.2313(2) 0.0456(7) Uani . . 1.000
    C C21 0.2375(2) 0.8955(3) 0.2002(2) 0.0612(9) Uani . . 1.000
    C C22 0.22377(19) 0.7867(3) 0.2674(2) 0.0575(9) Uani . . 1.000
    H H1 -0.061(2) 0.684(3) 0.661(3) 0.0628 Uiso . . 1.000
    H H2 -0.03578 0.63946 0.83474 0.0541 Uiso . . 1.000
    H H2A 0.220(2) 1.195(4) 0.187(4) 0.0839 Uiso . . 1.000
    H H3 -0.04612 0.68676 1.02018 0.0700 Uiso . . 1.000
    H H3A 0.2334(17) 0.480(3) 0.608(3) 0.0492 Uiso . . 1.000
    H H4 0.00691 0.88200 1.09092 0.0768 Uiso . . 1.000
    H H5 0.07271 1.02826 0.97730 0.0778 Uiso . . 1.000
    H H6 0.08444 0.98261 0.79188 0.0616 Uiso . . 1.000
    H H9 -0.14797 0.71205 0.51465 0.0573 Uiso . . 1.000
    H H10 -0.16905 0.68850 0.32930 0.0696 Uiso . . 1.000
    H H11 -0.06583 0.65794 0.21149 0.0710 Uiso . . 1.000
    H H12 0.05962 0.64081 0.27972 0.0571 Uiso . . 1.000
    H H16A 0.33112 0.75352 0.47749 0.0956 Uiso . . 1.000
    H H16B 0.35037 0.61882 0.53950 0.0956 Uiso . . 1.000
    H H16C 0.34011 0.61830 0.41172 0.0956 Uiso . . 1.000
    H H18 0.14104 0.94552 0.46751 0.0529 Uiso . . 1.000
    H H19 0.16312 1.12783 0.35368 0.0596 Uiso . . 1.000
    H H21 0.26212 0.88257 0.13302 0.0734 Uiso . . 1.000
    H H22 0.23907 0.70060 0.24582 0.0689 Uiso . . 1.000
_geom_special_details
;
Bond distances, angles etc have been calculated using the rounded fractional
coordinates. All su's are estimated from the variances of the (full)
variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_1
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C7 . . 1.218(3) ?
    O2 C20 . . 1.354(3) ?
    O2 H2A . . 0.76(4) ?
    N1 C7 . . 1.363(3) ?
    N1 C8 . . 1.414(3) ?
    N1 H1 . . 0.81(3) ?
    N2 N3 . . 1.369(3) ?
    N2 C14 . . 1.302(3) ?
    N3 C15 . . 1.306(3) ?
    N3 H3A . . 0.97(3) ?
    N4 C14 . . 1.385(3) ?
    N4 C15 . . 1.344(3) ?
    N4 C17 . . 1.443(3) ?
    C1 C2 . . 1.385(3) ?
    C1 C6 . . 1.380(4) ?
    C1 C7 . . 1.494(3) ?
    C2 C3 . . 1.389(4) ?
    C2 H2 . . 0.9300 ?
    C3 C4 . . 1.373(5) ?
    C3 H3 . . 0.9300 ?
    C4 C5 . . 1.371(5) ?
    C4 H4 . . 0.9300 ?
    C5 C6 . . 1.388(4) ?
    C5 H5 . . 0.9300 ?
    C6 H6 . . 0.9300 ?
    C8 C9 . . 1.399(3) ?
    C8 C13 . . 1.395(3) ?
    C9 C10 . . 1.377(4) ?
    C9 H9 . . 0.9300 ?
    C10 C11 . . 1.371(4) ?
    C10 H10 . . 0.9300 ?
    C11 C12 . . 1.384(4) ?
    C11 H11 . . 0.9300 ?
    C12 C13 . . 1.396(3) ?
    C12 H12 . . 0.9300 ?
    C13 C14 . . 1.471(3) ?
    C15 C16 . . 1.479(3) ?
    C16 H16A . . 0.9600 ?
    C16 H16B . . 0.9600 ?
    C16 H16C . . 0.9600 ?
    C17 C18 . . 1.376(3) ?
    C17 C22 . . 1.380(3) ?
    C18 C19 . . 1.378(4) ?
    C18 H18 . . 0.9300 ?
    C19 C20 . . 1.390(3) ?
    C19 H19 . . 0.9300 ?
    C20 C21 . . 1.378(4) ?
    C21 C22 . . 1.373(4) ?
    C21 H21 . . 0.9300 ?
    C22 H22 . . 0.9300 ?
loop_
    _geom_contact_atom_site_label_1
    _geom_contact_atom_site_label_2
    _geom_contact_distance
    _geom_contact_site_symmetry_1
    _geom_contact_site_symmetry_2
    _geom_contact_publ_flag
    Cl O2 3.090(2) . 1_545 ?
    Cl N1 3.372(2) . 2_564 ?
    Cl C2 3.627(3) . 2_564 ?
    Cl N3 3.068(2) . 3_554 ?
    Cl H2 2.9400 . 2_564 ?
    Cl H9 3.0700 . 2_564 ?
    Cl H1 2.58(3) . 2_564 ?
    Cl H22 2.9400 . . ?
    Cl H10 2.8800 . 4_565 ?
    Cl H2A 2.34(4) . 1_545 ?
    Cl H3A 2.14(3) . 3_554 ?
    O1 N4 3.106(3) . . ?
    O1 N2 3.187(3) . . ?
    O1 C18 3.165(3) . . ?
    O1 C13 2.941(3) . . ?
    O1 C14 2.710(3) . . ?
    O1 C21 3.291(4) . 3_555 ?
    O2 Cl 3.090(2) . 1_565 ?
    O1 H6 2.5200 . . ?
    O1 H18 2.3500 . . ?
    O1 H21 2.7100 . 3_555 ?
    O2 H9 2.8000 . 2_574 ?
    N1 Cl 3.372(2) . 2_565 ?
    N1 N2 3.141(3) . . ?
    N2 C7 3.281(3) . . ?
    N2 N4 2.212(3) . . ?
    N2 O1 3.187(3) . . ?
    N2 N1 3.141(3) . . ?
    N3 Cl 3.068(2) . 3_555 ?
    N3 N4 2.124(3) . . ?
    N4 N3 2.124(3) . . ?
    N4 O1 3.106(3) . . ?
    N1 H2 2.6300 . . ?
    N2 H3 2.6700 . 2_564 ?
    N3 H22 2.9200 . 3_555 ?
    N4 H12 2.8800 . . ?
    C2 Cl 3.627(3) . 2_565 ?
    C3 C16 3.505(4) . 3_555 ?
    C4 C16 3.524(4) . 3_555 ?
    C7 N2 3.281(3) . . ?
    C7 C14 3.105(3) . . ?
    C12 C17 3.301(3) . . ?
    C13 O1 2.941(3) . . ?
    C13 C18 3.550(3) . . ?
    C14 O1 2.710(3) . . ?
    C14 C7 3.105(3) . . ?
    C16 C22 3.338(4) . . ?
    C16 C4 3.524(4) . 3_554 ?
    C16 C3 3.505(4) . 3_554 ?
    C17 C12 3.301(3) . . ?
    C18 C13 3.550(3) . . ?
    C18 O1 3.165(3) . . ?
    C21 O1 3.291(4) . 3_554 ?
    C22 C16 3.338(4) . . ?
    C2 H19 2.9700 . 2_575 ?
    C2 H1 2.61(4) . . ?
    C4 H16A 2.9400 . 3_555 ?
    C5 H16A 2.8300 . 3_555 ?
    C6 H16A 3.0600 . 3_555 ?
    C8 H5 2.9400 . 2_574 ?
    C9 H5 2.7800 . 2_574 ?
    C12 H2 2.9200 . 2_564 ?
    C15 H21 3.0200 . 3_555 ?
    C15 H22 3.0900 . . ?
    C17 H16A 2.8600 . . ?
    C17 H12 2.9300 . . ?
    H1 H9 2.3400 . . ?
    H1 C2 2.61(4) . . ?
    H1 Cl 2.58(3) . 2_565 ?
    H1 H2 2.2100 . . ?
    H2 N1 2.6300 . . ?
    H2 H1 2.2100 . . ?
    H2 C12 2.9200 . 2_565 ?
    H2 Cl 2.9400 . 2_565 ?
    H2A H19 2.3500 . . ?
    H2A Cl 2.34(4) . 1_565 ?
    H3 H11 2.3700 . 1_556 ?
    H3 N2 2.6700 . 2_565 ?
    H3A H16B 2.5700 . . ?
    H3A Cl 2.14(3) . 3_555 ?
    H5 C9 2.7800 . 2_575 ?
    H5 C8 2.9400 . 2_575 ?
    H6 O1 2.5200 . . ?
    H9 Cl 3.0700 . 2_565 ?
    H9 O2 2.8000 . 2_575 ?
    H9 H1 2.3400 . . ?
    H10 Cl 2.8800 . 4_465 ?
    H11 H3 2.3700 . 1_554 ?
    H12 N4 2.8800 . . ?
    H12 C17 2.9300 . . ?
    H16A C4 2.9400 . 3_554 ?
    H16A C17 2.8600 . . ?
    H16A C5 2.8300 . 3_554 ?
    H16A C6 3.0600 . 3_554 ?
    H16B H3A 2.5700 . . ?
    H18 O1 2.3500 . . ?
    H19 C2 2.9700 . 2_574 ?
    H19 H2A 2.3500 . . ?
    H21 C15 3.0200 . 3_554 ?
    H21 O1 2.7100 . 3_554 ?
    H22 C15 3.0900 . . ?
    H22 N3 2.9200 . 3_554 ?
    H22 Cl 2.9400 . . ?
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_2
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C20 O2 H2A . . . 112(3) ?
    C7 N1 C8 . . . 123.6(2) ?
    N3 N2 C14 . . . 103.89(18) ?
    N2 N3 C15 . . . 112.5(2) ?
    C14 N4 C15 . . . 106.23(18) ?
    C14 N4 C17 . . . 129.23(18) ?
    C15 N4 C17 . . . 124.32(18) ?
    C8 N1 H1 . . . 114(3) ?
    C7 N1 H1 . . . 117(2) ?
    N2 N3 H3A . . . 119.5(18) ?
    C15 N3 H3A . . . 128.0(18) ?
    C2 C1 C6 . . . 119.6(2) ?
    C2 C1 C7 . . . 122.9(2) ?
    C6 C1 C7 . . . 117.5(2) ?
    C1 C2 C3 . . . 119.8(3) ?
    C2 C3 C4 . . . 120.6(3) ?
    C3 C4 C5 . . . 119.5(3) ?
    C4 C5 C6 . . . 120.8(3) ?
    C1 C6 C5 . . . 119.8(3) ?
    N1 C7 C1 . . . 116.83(19) ?
    O1 C7 N1 . . . 121.7(2) ?
    O1 C7 C1 . . . 121.5(2) ?
    C9 C8 C13 . . . 119.0(2) ?
    N1 C8 C13 . . . 123.5(2) ?
    N1 C8 C9 . . . 117.5(2) ?
    C8 C9 C10 . . . 120.6(2) ?
    C9 C10 C11 . . . 120.5(3) ?
    C10 C11 C12 . . . 119.9(2) ?
    C11 C12 C13 . . . 120.5(2) ?
    C12 C13 C14 . . . 118.2(2) ?
    C8 C13 C12 . . . 119.5(2) ?
    C8 C13 C14 . . . 122.0(2) ?
    N2 C14 N4 . . . 110.84(18) ?
    N2 C14 C13 . . . 124.17(19) ?
    N4 C14 C13 . . . 124.76(19) ?
    N3 C15 N4 . . . 106.5(2) ?
    N4 C15 C16 . . . 127.5(2) ?
    N3 C15 C16 . . . 126.0(2) ?
    N4 C17 C22 . . . 119.5(2) ?
    C18 C17 C22 . . . 120.3(2) ?
    N4 C17 C18 . . . 120.0(2) ?
    C17 C18 C19 . . . 119.7(2) ?
    C18 C19 C20 . . . 120.3(2) ?
    O2 C20 C19 . . . 122.9(2) ?
    C19 C20 C21 . . . 119.2(2) ?
    O2 C20 C21 . . . 117.9(2) ?
    C20 C21 C22 . . . 120.6(2) ?
    C17 C22 C21 . . . 119.8(3) ?
    C1 C2 H2 . . . 120.00 ?
    C3 C2 H2 . . . 120.00 ?
    C2 C3 H3 . . . 120.00 ?
    C4 C3 H3 . . . 120.00 ?
    C3 C4 H4 . . . 120.00 ?
    C5 C4 H4 . . . 120.00 ?
    C4 C5 H5 . . . 120.00 ?
    C6 C5 H5 . . . 120.00 ?
    C1 C6 H6 . . . 120.00 ?
    C5 C6 H6 . . . 120.00 ?
    C8 C9 H9 . . . 120.00 ?
    C10 C9 H9 . . . 120.00 ?
    C9 C10 H10 . . . 120.00 ?
    C11 C10 H10 . . . 120.00 ?
    C10 C11 H11 . . . 120.00 ?
    C12 C11 H11 . . . 120.00 ?
    C11 C12 H12 . . . 120.00 ?
    C13 C12 H12 . . . 120.00 ?
    C15 C16 H16A . . . 109.00 ?
    C15 C16 H16B . . . 109.00 ?
    C15 C16 H16C . . . 109.00 ?
    H16A C16 H16B . . . 110.00 ?
    H16A C16 H16C . . . 109.00 ?
    H16B C16 H16C . . . 109.00 ?
    C17 C18 H18 . . . 120.00 ?
    C19 C18 H18 . . . 120.00 ?
    C18 C19 H19 . . . 120.00 ?
    C20 C19 H19 . . . 120.00 ?
    C20 C21 H21 . . . 120.00 ?
    C22 C21 H21 . . . 120.00 ?
    C17 C22 H22 . . . 120.00 ?
    C21 C22 H22 . . . 120.00 ?
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
    C8 N1 C7 O1 . . . . -9.5(3) ?
    C8 N1 C7 C1 . . . . 170.21(19) ?
    C7 N1 C8 C9 . . . . -130.2(2) ?
    C7 N1 C8 C13 . . . . 49.5(3) ?
    C14 N2 N3 C15 . . . . -0.6(3) ?
    N3 N2 C14 N4 . . . . 0.5(2) ?
    N3 N2 C14 C13 . . . . 175.2(2) ?
    N2 N3 C15 N4 . . . . 0.4(3) ?
    N2 N3 C15 C16 . . . . -179.9(2) ?
    C15 N4 C14 N2 . . . . -0.2(2) ?
    C15 N4 C14 C13 . . . . -174.9(2) ?
    C17 N4 C14 N2 . . . . -175.0(2) ?
    C17 N4 C14 C13 . . . . 10.4(3) ?
    C14 N4 C15 N3 . . . . -0.1(2) ?
    C14 N4 C15 C16 . . . . -179.8(2) ?
    C17 N4 C15 N3 . . . . 175.0(2) ?
    C17 N4 C15 C16 . . . . -4.7(4) ?
    C14 N4 C17 C18 . . . . 67.0(3) ?
    C14 N4 C17 C22 . . . . -118.2(3) ?
    C15 N4 C17 C18 . . . . -106.9(3) ?
    C15 N4 C17 C22 . . . . 67.8(3) ?
    C6 C1 C2 C3 . . . . 1.3(4) ?
    C7 C1 C2 C3 . . . . -178.2(2) ?
    C2 C1 C6 C5 . . . . -1.5(4) ?
    C7 C1 C6 C5 . . . . 178.0(3) ?
    C2 C1 C7 O1 . . . . -159.0(2) ?
    C2 C1 C7 N1 . . . . 21.3(3) ?
    C6 C1 C7 O1 . . . . 21.5(3) ?
    C6 C1 C7 N1 . . . . -158.2(2) ?
    C1 C2 C3 C4 . . . . -0.2(4) ?
    C2 C3 C4 C5 . . . . -0.7(5) ?
    C3 C4 C5 C6 . . . . 0.5(5) ?
    C4 C5 C6 C1 . . . . 0.6(5) ?
    N1 C8 C9 C10 . . . . 179.5(2) ?
    C13 C8 C9 C10 . . . . -0.2(4) ?
    N1 C8 C13 C12 . . . . -177.8(2) ?
    N1 C8 C13 C14 . . . . 8.3(3) ?
    C9 C8 C13 C12 . . . . 1.9(3) ?
    C9 C8 C13 C14 . . . . -172.0(2) ?
    C8 C9 C10 C11 . . . . -1.6(4) ?
    C9 C10 C11 C12 . . . . 1.6(5) ?
    C10 C11 C12 C13 . . . . 0.2(4) ?
    C11 C12 C13 C8 . . . . -1.9(4) ?
    C11 C12 C13 C14 . . . . 172.2(2) ?
    C8 C13 C14 N2 . . . . 52.0(3) ?
    C8 C13 C14 N4 . . . . -134.1(2) ?
    C12 C13 C14 N2 . . . . -122.0(3) ?
    C12 C13 C14 N4 . . . . 52.0(3) ?
    N4 C17 C18 C19 . . . . 175.6(2) ?
    C22 C17 C18 C19 . . . . 0.9(4) ?
    N4 C17 C22 C21 . . . . -175.2(3) ?
    C18 C17 C22 C21 . . . . -0.5(4) ?
    C17 C18 C19 C20 . . . . -0.6(4) ?
    C18 C19 C20 O2 . . . . -178.2(3) ?
    C18 C19 C20 C21 . . . . 0.1(4) ?
    O2 C20 C21 C22 . . . . 178.7(3) ?
    C19 C20 C21 C22 . . . . 0.3(4) ?
    C20 C21 C22 C17 . . . . -0.1(5) ?
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
    N1 H1 Cl 2_565 0.81(3) 2.58(3) 3.372(2) 166(3) yes
    O2 H2A Cl 1_565 0.76(4) 2.34(4) 3.090(2) 171(5) yes
    N3 H3A Cl 3_555 0.97(3) 2.14(3) 3.068(2) 158(3) yes
    C18 H18 O1 . 0.9300 2.3500 3.165(3) 146.00 yes
    C16 H16A Cg2 3_554 0.9600 2.8400 3.367(3) 115.00 yes
