#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/91/2239153.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2239153
loop_
_publ_author_name
'Bel Haj Salah, Raoudha'
'Khederi, Lamia'
'Rzaigui, Mohamed'
_publ_section_title
;
 Hexakis(3-chloro-2-methylanilinium) cyclohexaphosphate dihydrate
;
_journal_coeditor_code           FJ2652
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o61
_journal_paper_doi               10.1107/S1600536813033230
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          '6C7 H9 Cl N +, P6 O18 6-, 2H2 O'
_chemical_formula_moiety         '6(C7 H9 Cl N +), O18 P6 6-, 2(H2 O)'
_chemical_formula_sum            'C42 H58 Cl6 N6 O20 P6'
_chemical_formula_weight         1365.46
_chemical_name_systematic
;
Hexakis(3-chloro-2-methylanilinium) cyclohexaphosphate dihydrate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.48(2)
_cell_angle_beta                 103.74(4)
_cell_angle_gamma                112.25(4)
_cell_formula_units_Z            1
_cell_length_a                   9.576(5)
_cell_length_b                   10.187(4)
_cell_length_c                   17.392(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     1498.5(12)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0608
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7464
_diffrn_reflns_theta_full        27.98
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        5
_diffrn_standards_interval_time  120
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.391
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         7229
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0496
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0596P)²+0.4583P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1281
_reflns_number_gt                4800
_reflns_number_total             7229
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fj2652sup1.cf
_cod_data_source_block           I
_cod_database_code               2239153
_cod_database_fobs_code          2239153
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
P P1 0.10693(8) 0.76984(7) 0.50600(4) 0.0233(2) Uani 1.000
P P2 0.32227(7) 0.62757(7) 0.52138(4) 0.0217(2) Uani 1.000
P P3 0.13627(8) 0.34633(7) 0.41193(4) 0.0236(2) Uani 1.000
O O1 0.2396(2) 0.9092(2) 0.54611(13) 0.0389(7) Uani 1.000
O O2 -0.0196(2) 0.7621(2) 0.43465(12) 0.0320(6) Uani 1.000
O O3 0.1712(2) 0.6560(2) 0.47796(11) 0.0302(6) Uani 1.000
O O4 0.3518(2) 0.6539(2) 0.61045(11) 0.0301(6) Uani 1.000
O O5 0.4520(2) 0.7054(2) 0.48872(13) 0.0363(7) Uani 1.000
O O6 0.2550(2) 0.4574(2) 0.49312(12) 0.0333(6) Uani 1.000
O O7 0.1293(2) 0.4211(2) 0.34254(12) 0.0329(6) Uani 1.000
O O8 0.1743(2) 0.2189(2) 0.41061(12) 0.0343(6) Uani 1.000
O O9 0.0321(2) 0.6948(2) 0.57240(12) 0.0327(6) Uani 1.000
Cl Cl1 0.34937(16) -0.02530(14) 0.04005(7) 0.0821(5) Uani 1.000
N N1 0.3436(3) 0.1365(3) 0.32844(15) 0.0306(8) Uani 1.000
C C1 0.2839(3) 0.1210(3) 0.24115(17) 0.0308(8) Uani 1.000
C C2 0.3467(4) 0.0618(3) 0.19071(19) 0.0375(10) Uani 1.000
C C3 0.2856(4) 0.0540(4) 0.1089(2) 0.0483(11) Uani 1.000
C C4 0.1740(5) 0.1046(4) 0.0786(2) 0.0564(11) Uani 1.000
C C5 0.1155(4) 0.1631(4) 0.1303(2) 0.0560(14) Uani 1.000
C C6 0.1694(4) 0.1698(3) 0.21233(19) 0.0416(10) Uani 1.000
C C7 0.4738(5) 0.0117(4) 0.2232(2) 0.0579(16) Uani 1.000
Cl Cl2 0.6890(2) 0.81050(16) 0.11837(7) 0.1000(6) Uani 1.000
N N2 0.7057(3) 0.8023(3) 0.41707(15) 0.0281(8) Uani 1.000
C C8 0.6282(3) 0.7400(3) 0.33153(17) 0.0292(8) Uani 1.000
C C9 0.6979(4) 0.8032(3) 0.27466(18) 0.0359(10) Uani 1.000
C C10 0.6160(5) 0.7370(4) 0.1948(2) 0.0546(13) Uani 1.000
C C11 0.4744(6) 0.6175(5) 0.1737(3) 0.0785(18) Uani 1.000
C C12 0.4108(5) 0.5590(5) 0.2319(3) 0.0726(17) Uani 1.000
C C13 0.4874(4) 0.6200(4) 0.3115(2) 0.0464(11) Uani 1.000
C C14 0.8500(4) 0.9359(4) 0.2981(2) 0.0518(12) Uani 1.000
Cl Cl3 1.0171(2) 0.67872(17) 0.06613(8) 0.1091(7) Uani 1.000
N N3 0.8848(3) 0.5080(3) 0.32105(15) 0.0317(8) Uani 1.000
C C15 0.8371(3) 0.4984(3) 0.23430(18) 0.0345(9) Uani 1.000
C C16 0.9415(4) 0.5911(3) 0.19903(19) 0.0403(10) Uani 1.000
C C17 0.8953(5) 0.5702(4) 0.1164(2) 0.0641(14) Uani 1.000
C C18 0.7528(7) 0.4644(6) 0.0704(3) 0.109(2) Uani 1.000
C C19 0.6514(6) 0.3770(6) 0.1070(3) 0.105(2) Uani 1.000
C C20 0.6930(4) 0.3946(4) 0.1898(2) 0.0662(12) Uani 1.000
C C21 1.0981(4) 0.7057(4) 0.2497(3) 0.0616(14) Uani 1.000
O O1W 0.5687(3) 0.0657(3) 0.59977(17) 0.0498(9) Uani 1.000
H H1A 0.284(4) 0.166(4) 0.357(2) 0.056(11) Uiso 1.000
H H1B 0.350(4) 0.050(4) 0.346(2) 0.049(10) Uiso 1.000
H H1C 0.446(4) 0.210(4) 0.3448(19) 0.039(9) Uiso 1.000
H H4 0.13811 0.09937 0.02333 0.0851 Uiso 1.000
H H5 0.03996 0.19805 0.11032 0.0839 Uiso 1.000
H H6 0.12852 0.20698 0.24769 0.0624 Uiso 1.000
H H7A 0.49965 0.02657 0.28092 0.0874 Uiso 1.000
H H7B 0.43730 -0.08912 0.20193 0.0874 Uiso 1.000
H H7C 0.56571 0.06563 0.20757 0.0874 Uiso 1.000
H H2A 0.640(4) 0.755(4) 0.445(2) 0.047(10) Uiso 1.000
H H2B 0.797(5) 0.786(4) 0.431(2) 0.059(11) Uiso 1.000
H H2C 0.726(4) 0.896(4) 0.427(2) 0.043(9) Uiso 1.000
H H11 0.42203 0.57662 0.11971 0.1168 Uiso 1.000
H H12 0.31566 0.47788 0.21759 0.1088 Uiso 1.000
H H13 0.44471 0.58085 0.35145 0.0694 Uiso 1.000
H H14A 0.88732 0.96426 0.35569 0.0779 Uiso 1.000
H H14B 0.92709 0.91552 0.27887 0.0779 Uiso 1.000
H H14C 0.83286 1.01277 0.27464 0.0779 Uiso 1.000
H H3A 0.979(5) 0.484(5) 0.334(3) 0.089(15) Uiso 1.000
H H3B 0.802(5) 0.442(4) 0.344(2) 0.066(12) Uiso 1.000
H H3C 0.912(4) 0.591(4) 0.348(2) 0.058(12) Uiso 1.000
H H18 0.72554 0.45254 0.01451 0.1635 Uiso 1.000
H H19 0.55476 0.30596 0.07609 0.1573 Uiso 1.000
H H20 0.62411 0.33662 0.21526 0.0991 Uiso 1.000
H H21A 1.10761 0.70244 0.30568 0.0919 Uiso 1.000
H H21B 1.18180 0.68856 0.23587 0.0919 Uiso 1.000
H H21C 1.10459 0.79895 0.23990 0.0919 Uiso 1.000
H H1W 0.476(6) 0.015(5) 0.576(3) 0.085(17) Uiso 1.000
H H2W 0.583(5) 0.135(5) 0.577(3) 0.083(16) Uiso 1.000
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'
Cl Cl 0.1484 0.1585 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 4 -1
2 3 -2
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
O1 P1 O2 . 120.42(13)
O1 P1 O3 . 110.23(13)
O1 P1 O9 . 108.66(12)
O2 P1 O3 . 105.54(12)
O2 P1 O9 . 110.27(13)
O3 P1 O9 . 99.71(11)
O3 P2 O4 . 110.07(12)
O3 P2 O5 . 108.64(12)
O3 P2 O6 . 100.22(12)
O4 P2 O5 . 118.09(13)
O4 P2 O6 . 106.34(12)
O5 P2 O6 . 112.00(12)
O6 P3 O7 . 110.89(12)
O6 P3 O8 . 106.05(12)
O6 P3 O9 2_566 102.62(12)
O7 P3 O8 . 121.53(13)
O7 P3 O9 2_566 104.67(12)
O8 P3 O9 2_566 109.53(12)
P1 O3 P2 . 130.72(13)
P2 O6 P3 . 134.20(14)
P1 O9 P3 2_566 133.29(14)
H1W O1W H2W . 101(5)
H1A N1 H1B . 108(3)
H1A N1 H1C . 107(3)
C1 N1 H1B . 114(2)
C1 N1 H1C . 107(2)
H1B N1 H1C . 108(3)
C1 N1 H1A . 113(2)
H2B N2 H2C . 112(4)
H2A N2 H2B . 110(3)
H2A N2 H2C . 109(4)
C8 N2 H2A . 108(2)
C8 N2 H2B . 107(2)
C8 N2 H2C . 111(2)
C15 N3 H3B . 116(2)
H3B N3 H3C . 104(3)
C15 N3 H3C . 114(2)
C15 N3 H3A . 107(3)
H3A N3 H3C . 107(4)
H3A N3 H3B . 109(4)
C2 C1 C6 . 122.5(3)
N1 C1 C6 . 117.9(3)
N1 C1 C2 . 119.6(3)
C3 C2 C7 . 122.4(3)
C1 C2 C7 . 121.9(3)
C1 C2 C3 . 115.7(3)
Cl1 C3 C2 . 119.6(3)
C2 C3 C4 . 123.0(4)
Cl1 C3 C4 . 117.4(3)
C3 C4 C5 . 119.6(3)
C4 C5 C6 . 119.7(4)
C1 C6 C5 . 119.5(3)
C5 C4 H4 . 120.00
C3 C4 H4 . 120.00
C4 C5 H5 . 120.00
C6 C5 H5 . 120.00
C5 C6 H6 . 120.00
C1 C6 H6 . 120.00
C2 C7 H7C . 109.00
C2 C7 H7A . 109.00
C2 C7 H7B . 109.00
H7A C7 H7B . 109.00
H7A C7 H7C . 109.00
H7B C7 H7C . 109.00
N2 C8 C13 . 117.5(3)
C9 C8 C13 . 123.1(3)
N2 C8 C9 . 119.4(3)
C10 C9 C14 . 122.5(3)
C8 C9 C14 . 122.0(3)
C8 C9 C10 . 115.5(3)
Cl2 C10 C9 . 119.5(3)
C9 C10 C11 . 122.1(4)
Cl2 C10 C11 . 118.4(3)
C10 C11 C12 . 120.2(4)
C11 C12 C13 . 119.9(5)
C8 C13 C12 . 119.2(4)
C12 C11 H11 . 120.00
C10 C11 H11 . 120.00
C13 C12 H12 . 120.00
C11 C12 H12 . 120.00
C8 C13 H13 . 120.00
C12 C13 H13 . 120.00
C9 C14 H14C . 109.00
C9 C14 H14B . 109.00
H14A C14 H14C . 109.00
C9 C14 H14A . 109.00
H14A C14 H14B . 109.00
H14B C14 H14C . 109.00
C16 C15 C20 . 122.3(3)
N3 C15 C16 . 118.9(3)
N3 C15 C20 . 118.8(3)
C15 C16 C21 . 121.1(3)
C17 C16 C21 . 122.5(4)
C15 C16 C17 . 116.4(3)
Cl3 C17 C18 . 117.5(3)
C16 C17 C18 . 122.2(4)
Cl3 C17 C16 . 120.3(3)
C17 C18 C19 . 119.9(5)
C18 C19 C20 . 119.7(5)
C15 C20 C19 . 119.3(4)
C17 C18 H18 . 120.00
C19 C18 H18 . 120.00
C20 C19 H19 . 120.00
C18 C19 H19 . 120.00
C15 C20 H20 . 120.00
C19 C20 H20 . 120.00
C16 C21 H21B . 109.00
C16 C21 H21C . 109.00
C16 C21 H21A . 109.00
H21A C21 H21C . 109.00
H21B C21 H21C . 110.00
H21A C21 H21B . 109.00
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C3 . 1.741(4)
Cl2 C10 . 1.737(4)
Cl3 C17 . 1.734(5)
P1 O2 . 1.487(2)
P1 O9 . 1.596(2)
P1 O3 . 1.599(2)
P1 O1 . 1.475(2)
P2 O5 . 1.468(2)
P2 O3 . 1.606(2)
P2 O4 . 1.490(2)
P2 O6 . 1.591(2)
P3 O9 2_566 1.601(2)
P3 O7 . 1.478(2)
P3 O8 . 1.475(2)
P3 O6 . 1.606(2)
O1W H1W . 0.82(5)
O1W H2W . 0.82(5)
N1 C1 . 1.462(4)
N1 H1C . 0.94(4)
N1 H1B . 0.97(4)
N1 H1A . 0.95(4)
N2 C8 . 1.462(4)
N2 H2B . 0.93(5)
N2 H2A . 0.90(4)
N2 H2C . 0.89(4)
N3 C15 . 1.453(4)
N3 H3C . 0.85(4)
N3 H3B . 1.01(4)
N3 H3A . 1.00(5)
C1 C6 . 1.375(5)
C1 C2 . 1.392(5)
C2 C7 . 1.500(6)
C2 C3 . 1.387(5)
C3 C4 . 1.370(6)
C4 C5 . 1.373(6)
C5 C6 . 1.384(5)
C4 H4 . 0.9300
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 H7C . 0.9600
C7 H7B . 0.9600
C7 H7A . 0.9600
C8 C9 . 1.388(4)
C8 C13 . 1.377(5)
C9 C14 . 1.502(5)
C9 C10 . 1.391(5)
C10 C11 . 1.378(7)
C11 C12 . 1.365(7)
C12 C13 . 1.371(6)
C11 H11 . 0.9300
C12 H12 . 0.9300
C13 H13 . 0.9300
C14 H14C . 0.9600
C14 H14A . 0.9600
C14 H14B . 0.9600
C15 C16 . 1.391(5)
C15 C20 . 1.372(5)
C16 C21 . 1.508(6)
C16 C17 . 1.373(5)
C17 C18 . 1.377(7)
C18 C19 . 1.367(8)
C19 C20 . 1.378(6)
C18 H18 . 0.9300
C19 H19 . 0.9300
C20 H20 . 0.9300
C21 H21C . 0.9600
C21 H21A . 0.9600
C21 H21B . 0.9600
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 H1A O8 . 0.95(4) 1.76(4) 2.705(4) 179(5) y
N1 H1B O1W 2_656 0.97(4) 1.85(4) 2.779(4) 160(3) y
N1 H1C O4 2_666 0.94(4) 1.83(4) 2.766(4) 173(3) y
O1W H1W O1 1_545 0.82(5) 2.02(6) 2.813(4) 164(5) y
O1W H2W O5 2_666 0.82(5) 2.14(5) 2.934(4) 163(5) y
N2 H2A O5 . 0.90(4) 2.02(4) 2.871(4) 156(4) y
N2 H2B O2 1_655 0.93(5) 1.85(5) 2.763(4) 166(3) y
N2 H2C O1 2_676 0.89(4) 1.89(4) 2.775(4) 176(4) y
N3 H3A O7 1_655 1.00(5) 1.77(5) 2.759(4) 171(5) y
N3 H3B O4 2_666 1.01(4) 1.83(4) 2.834(4) 172(4) y
N3 H3C O2 1_655 0.85(4) 2.00(4) 2.827(4) 166(3) y
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_4
_geom_torsion
O1 P1 O3 P2 . . . 38.7(2)
O2 P1 O3 P2 . . . 170.22(16)
O9 P1 O3 P2 . . . -75.42(19)
O2 P1 O9 P3 . . 2_566 -19.0(2)
O3 P1 O9 P3 . . 2_566 -129.62(18)
O1 P1 O9 P3 . . 2_566 115.04(19)
O4 P2 O3 P1 . . . 33.9(2)
O5 P2 O3 P1 . . . -96.79(18)
O5 P2 O6 P3 . . . -79.6(2)
O6 P2 O3 P1 . . . 145.66(17)
O3 P2 O6 P3 . . . 35.4(2)
O4 P2 O6 P3 . . . 150.01(19)
O7 P3 O6 P2 . . . 22.7(2)
O8 P3 O6 P2 . . . 156.50(19)
O9 P3 O6 P2 2_566 . . -88.6(2)
O6 P3 O9 P1 2_566 2_566 . 61.0(2)
O7 P3 O9 P1 2_566 2_566 . 176.90(17)
O8 P3 O9 P1 2_566 2_566 . -51.3(2)
N1 C1 C2 C3 . . . -178.7(3)
N1 C1 C2 C7 . . . 0.6(5)
C6 C1 C2 C3 . . . -0.4(5)
C6 C1 C2 C7 . . . 178.8(3)
N1 C1 C6 C5 . . . 177.0(3)
C2 C1 C6 C5 . . . -1.3(5)
C1 C2 C3 Cl1 . . . -177.2(3)
C1 C2 C3 C4 . . . 1.9(5)
C7 C2 C3 Cl1 . . . 3.6(5)
C7 C2 C3 C4 . . . -177.3(4)
Cl1 C3 C4 C5 . . . 177.5(3)
C2 C3 C4 C5 . . . -1.6(6)
C3 C4 C5 C6 . . . -0.3(6)
C4 C5 C6 C1 . . . 1.6(5)
N2 C8 C9 C10 . . . -179.9(3)
N2 C8 C9 C14 . . . -1.1(5)
C13 C8 C9 C10 . . . -0.1(5)
C13 C8 C9 C14 . . . 178.7(4)
N2 C8 C13 C12 . . . 179.7(4)
C9 C8 C13 C12 . . . -0.2(6)
C8 C9 C10 Cl2 . . . 177.9(3)
C8 C9 C10 C11 . . . 0.6(6)
C14 C9 C10 Cl2 . . . -1.0(6)
C14 C9 C10 C11 . . . -178.3(4)
Cl2 C10 C11 C12 . . . -178.1(4)
C9 C10 C11 C12 . . . -0.8(8)
C10 C11 C12 C13 . . . 0.5(8)
C11 C12 C13 C8 . . . -0.1(7)
N3 C15 C16 C17 . . . 175.3(3)
N3 C15 C16 C21 . . . -3.4(5)
C20 C15 C16 C17 . . . -2.3(5)
C20 C15 C16 C21 . . . 179.0(4)
N3 C15 C20 C19 . . . -175.0(4)
C16 C15 C20 C19 . . . 2.5(6)
C15 C16 C17 Cl3 . . . -179.5(3)
C15 C16 C17 C18 . . . 0.6(7)
C21 C16 C17 Cl3 . . . -0.8(6)
C21 C16 C17 C18 . . . 179.3(5)
Cl3 C17 C18 C19 . . . -179.2(5)
C16 C17 C18 C19 . . . 0.7(9)
C17 C18 C19 C20 . . . -0.5(9)
C18 C19 C20 C15 . . . -1.0(8)
