#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/25/2222520.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2222520
loop_
_publ_author_name
'Tokarčík, Miroslav'
'Gowda, B. Thimme'
'Kožíšek, Jozef'
'Sowmya, B. P.'
'Fuess, Hartmut'
_publ_section_title
;
 4-Chloro-N-(2,6-dichlorophenyl)benzamide
;
_journal_coeditor_code           ZL2218
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1637
_journal_page_last               o1638
_journal_paper_doi               10.1107/S160053680902265X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C13 H8 Cl3 N O'
_chemical_formula_moiety         'C13 H8 Cl3 N O'
_chemical_formula_sum            'C13 H8 Cl3 N O'
_chemical_formula_weight         300.55
_chemical_name_systematic
;
4-Chloro-N-(2,6-dichlorophenyl)benzamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.3678(13)
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   16.9411(3)
_cell_length_b                   16.3246(2)
_cell_length_c                   19.5505(3)
_cell_measurement_reflns_used    40513
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.6
_cell_measurement_theta_min      2.98
_cell_volume                     5383.11(14)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2008)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2008)
;
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2001)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and WinGX
(Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '4-circle kappa geometry goniometer'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       'ω scans with κ offsets'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            180094
_diffrn_reflns_theta_full        25.75
_diffrn_reflns_theta_max         25.75
_diffrn_reflns_theta_min         2.32
_diffrn_standards_decay_%        0.5
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis RED (Oxford Diffraction, 2008), based on Clark & Reid
(1995)]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.225
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     670
_refine_ls_number_reflns         10278
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.082
_refine_ls_R_factor_gt           0.041
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.1072
_reflns_number_gt                5984
_reflns_number_total             10264
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2218.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222520
_cod_database_fobs_code          2222520
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'
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
N N1A -0.01521(12) 0.24995(13) 0.20152(9) 0.0679(6) Uani d D 1 . .
H H1N -0.0020(14) 0.2564(15) 0.1607(9) 0.081 Uiso d D 1 . .
O O1A 0.00098(11) 0.27519(12) 0.31328(7) 0.0872(6) Uani d . 1 . .
Cl Cl1A 0.34739(5) 0.42659(5) 0.23734(4) 0.1008(3) Uani d . 1 . .
Cl Cl2A -0.02618(5) 0.06753(5) 0.21458(4) 0.1059(3) Uani d . 1 . .
Cl Cl3A -0.14461(5) 0.37320(5) 0.19803(4) 0.1009(3) Uani d . 1 . .
C C1A 0.02724(13) 0.27901(14) 0.25719(10) 0.0578(6) Uani d . 1 . .
C C2A 0.10565(13) 0.31648(13) 0.24908(9) 0.0517(5) Uani d U 1 . .
C C3A 0.15350(15) 0.33685(15) 0.30778(11) 0.0658(6) Uani d U 1 . .
H H3A 0.1354 0.3275 0.3505 0.079 Uiso calc R 1 . .
C C4A 0.22717(16) 0.37056(15) 0.30429(12) 0.0711(7) Uani d . 1 . .
H H4A 0.2586 0.3838 0.3443 0.085 Uiso calc R 1 . .
C C5A 0.25378(14) 0.38453(14) 0.24193(12) 0.0643(6) Uani d . 1 . .
C C6A 0.20812(16) 0.36548(17) 0.18329(12) 0.0800(8) Uani d . 1 . .
H H6A 0.2264 0.3757 0.1407 0.096 Uiso calc R 1 . .
C C7A 0.13480(15) 0.33111(16) 0.18723(11) 0.0735(7) Uani d . 1 . .
H H7A 0.1041 0.3174 0.1469 0.088 Uiso calc R 1 . .
C C8A -0.09215(14) 0.21751(17) 0.20417(10) 0.0627(6) Uani d . 1 . .
C C9A -0.10499(15) 0.13470(18) 0.20852(11) 0.0702(7) Uani d . 1 . .
C C10A -0.18105(19) 0.10314(19) 0.20735(12) 0.0800(8) Uani d . 1 . .
H H10A -0.1888 0.047 0.2109 0.096 Uiso calc R 1 . .
C C11A -0.24487(17) 0.1553(2) 0.20087(12) 0.0820(8) Uani d . 1 . .
H H11A -0.296 0.1342 0.1987 0.098 Uiso calc R 1 . .
C C12A -0.23399(16) 0.2376(2) 0.19764(11) 0.0807(8) Uani d . 1 . .
H H12A -0.2775 0.2726 0.1939 0.097 Uiso calc R 1 . .
C C13A -0.15816(16) 0.26914(17) 0.19990(10) 0.0712(7) Uani d . 1 . .
N N1B 0.54004(11) 0.25961(12) 0.28954(8) 0.0578(5) Uani d D 1 . .
H H2N 0.5318(13) 0.2534(14) 0.2481(8) 0.069 Uiso d D 1 . .
O O1B 0.49853(9) 0.25248(11) 0.39413(7) 0.0762(5) Uani d . 1 . .
Cl Cl1B 0.17328(5) 0.09853(6) 0.22580(6) 0.1275(3) Uani d . 1 . .
Cl Cl2B 0.65068(5) 0.13398(5) 0.35411(4) 0.1043(3) Uani d . 1 . .
Cl Cl3B 0.56847(5) 0.43598(5) 0.26545(4) 0.1017(3) Uani d . 1 . .
C C1B 0.48504(13) 0.24196(13) 0.33249(10) 0.0517(5) Uani d . 1 . .
C C2B 0.40793(12) 0.20796(12) 0.30239(10) 0.0484(5) Uani d . 1 . .
C C3B 0.35060(15) 0.19335(15) 0.34661(12) 0.0658(6) Uani d . 1 . .
H H3B 0.3606 0.2064 0.3929 0.079 Uiso calc R 1 . .
C C4B 0.27899(16) 0.15970(16) 0.32283(16) 0.0787(7) Uani d . 1 . .
H H4B 0.2407 0.1497 0.353 0.094 Uiso calc R 1 . .
C C5B 0.26417(15) 0.14095(15) 0.25493(17) 0.0753(7) Uani d . 1 . .
C C6B 0.31894(17) 0.15589(18) 0.21067(14) 0.0841(8) Uani d . 1 . .
H H6B 0.308 0.1438 0.1643 0.101 Uiso calc R 1 . .
C C7B 0.39097(15) 0.18910(15) 0.23434(11) 0.0700(7) Uani d . 1 . .
H H7B 0.4287 0.1989 0.2037 0.084 Uiso calc R 1 . .
C C8B 0.61598(13) 0.28835(14) 0.31361(9) 0.0520(5) Uani d . 1 . .
C C9B 0.67220(15) 0.23618(16) 0.34592(11) 0.0665(6) Uani d . 1 . .
C C10B 0.74665(17) 0.2637(2) 0.36897(13) 0.0840(8) Uani d . 1 . .
H H10B 0.7835 0.2283 0.3912 0.101 Uiso calc R 1 . .
C C11B 0.76574(18) 0.3435(2) 0.35883(14) 0.0883(9) Uani d . 1 . .
H H11B 0.8162 0.3621 0.374 0.106 Uiso calc R 1 . .
C C12B 0.71239(18) 0.39649(18) 0.32688(13) 0.0803(8) Uani d . 1 . .
H H12B 0.7263 0.4507 0.3199 0.096 Uiso calc R 1 . .
C C13B 0.63704(14) 0.36865(15) 0.30494(10) 0.0630(6) Uani d . 1 . .
N N1C 0.54579(11) 0.23320(10) 0.53835(8) 0.0508(4) Uani d D 1 . .
H H3N 0.5371(12) 0.2468(13) 0.4968(8) 0.061 Uiso d D 1 . .
O O1C 0.56197(9) 0.27476(9) 0.64809(7) 0.0632(4) Uani d . 1 . .
Cl Cl1C 0.62723(4) 0.63315(4) 0.49957(4) 0.0881(2) Uani d . 1 . .
Cl Cl2C 0.38314(4) 0.16952(5) 0.55737(4) 0.0940(2) Uani d . 1 . .
Cl Cl3C 0.69772(5) 0.14330(5) 0.54692(4) 0.1055(3) Uani d U 1 . .
C C1C 0.56049(11) 0.29103(13) 0.58689(10) 0.0459(5) Uani d . 1 . .
C C2C 0.57685(11) 0.37500(12) 0.56292(9) 0.0441(5) Uani d . 1 . .
C C3C 0.56156(13) 0.44075(14) 0.60366(10) 0.0588(6) Uani d . 1 . .
H H3C 0.5406 0.4316 0.6453 0.071 Uiso calc R 1 . .
C C4C 0.57648(14) 0.51957(15) 0.58425(12) 0.0656(6) Uani d . 1 . .
H H4C 0.5645 0.5633 0.6119 0.079 Uiso calc R 1 . .
C C5C 0.60899(12) 0.53327(13) 0.52411(11) 0.0554(6) Uani d . 1 . .
C C6C 0.62633(14) 0.46970(14) 0.48319(11) 0.0638(6) Uani d . 1 . .
H H6C 0.6492 0.4795 0.4426 0.077 Uiso calc R 1 . .
C C7C 0.60982(13) 0.39061(13) 0.50214(10) 0.0566(6) Uani d . 1 . .
H H7C 0.621 0.3473 0.4737 0.068 Uiso calc R 1 . .
C C8C 0.54059(15) 0.14968(13) 0.55637(9) 0.0543(6) Uani d U 1 . .
C C9C 0.46937(16) 0.11342(14) 0.56777(11) 0.0653(6) Uani d U 1 . .
C C10C 0.4646(2) 0.03189(16) 0.58582(12) 0.0832(8) Uani d . 1 . .
H H10C 0.416 0.0085 0.593 0.1 Uiso calc R 1 . .
C C11C 0.5325(3) -0.01375(18) 0.59289(13) 0.0975(10) Uani d . 1 . .
H H11C 0.5298 -0.0685 0.6057 0.117 Uiso calc R 1 . .
C C12C 0.6042(2) 0.01942(19) 0.58145(13) 0.0915(9) Uani d . 1 . .
H H12C 0.6499 -0.0125 0.5859 0.11 Uiso calc R 1 . .
C C13C 0.60779(16) 0.10095(15) 0.56319(11) 0.0683(6) Uani d U 1 . .
N N1D 1.00625(13) 0.21879(12) 0.44495(8) 0.0716(6) Uani d D 1 . .
H H4N 0.9902(15) 0.2400(14) 0.4068(10) 0.086 Uiso d D 1 . .
O O1D 0.98706(12) 0.21685(11) 0.55695(7) 0.0870(6) Uani d . 1 . .
Cl Cl1D 0.82750(6) 0.58103(5) 0.47748(5) 0.1224(3) Uani d . 1 . .
Cl Cl2D 1.17656(5) 0.21164(5) 0.49982(4) 0.1061(3) Uani d . 1 . .
Cl Cl3D 0.90147(6) 0.08528(6) 0.38692(4) 0.1133(3) Uani d U 1 . .
C C1D 0.98079(14) 0.25205(15) 0.50152(10) 0.0637(6) Uani d . 1 . .
C C2D 0.94263(13) 0.33420(15) 0.49198(10) 0.0574(6) Uani d . 1 . .
C C3D 0.88233(16) 0.35364(17) 0.53201(11) 0.0741(7) Uani d . 1 . .
H H3D 0.866 0.3153 0.5629 0.089 Uiso calc R 1 . .
C C4D 0.84624(16) 0.42912(18) 0.52672(12) 0.0783(8) Uani d . 1 . .
H H4D 0.8052 0.4417 0.5534 0.094 Uiso calc R 1 . .
C C5D 0.87110(15) 0.48473(16) 0.48241(14) 0.0705(7) Uani d . 1 . .
C C6D 0.93043(15) 0.46719(15) 0.44139(12) 0.0681(6) Uani d . 1 . .
H H6D 0.9464 0.506 0.4107 0.082 Uiso calc R 1 . .
C C7D 0.96600(13) 0.39125(15) 0.44644(11) 0.0589(6) Uani d . 1 . .
H H7D 1.0061 0.3786 0.4188 0.071 Uiso calc R 1 . .
C C8D 1.04163(19) 0.14073(17) 0.44522(11) 0.0743(8) Uani d . 1 . .
C C9D 1.12048(19) 0.12862(17) 0.47012(12) 0.0820(8) Uani d . 1 . .
C C10D 1.1547(2) 0.0528(2) 0.47083(15) 0.0975(10) Uani d DU 1 . .
H H10D 1.2093(14) 0.046(2) 0.4889(15) 0.117 Uiso d D 1 . .
C C11D 1.1102(3) -0.0126(2) 0.44464(17) 0.1084(12) Uani d DU 1 . .
H H11D 1.1308(19) -0.0659(15) 0.4433(16) 0.13 Uiso d D 1 . .
C C12D 1.0336(3) -0.0034(2) 0.41819(16) 0.1030(11) Uani d D 1 . .
H H12D 0.9978(18) -0.0453(18) 0.4045(16) 0.124 Uiso d D 1 . .
C C13D 0.99924(19) 0.07337(19) 0.41871(12) 0.0846(8) Uani d U 1 . .
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 0 '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 0.006 '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'
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
C1A N1A C8A . . 122.16(17) ?
C1A N1A H1N . . 123.3(17) ?
C8A N1A H1N . . 113.8(17) ?
O1A C1A N1A . . 120.0(2) ?
O1A C1A C2A . . 121.40(19) ?
N1A C1A C2A . . 118.61(18) ?
C7A C2A C3A . . 117.3(2) ?
C7A C2A C1A . . 124.51(19) ?
C3A C2A C1A . . 118.14(19) ?
C4A C3A C2A . . 121.4(2) ?
C4A C3A H3A . . 119.3 ?
C2A C3A H3A . . 119.3 ?
C5A C4A C3A . . 119.5(2) ?
C5A C4A H4A . . 120.3 ?
C3A C4A H4A . . 120.3 ?
C6A C5A C4A . . 120.6(2) ?
C6A C5A Cl1A . . 119.8(2) ?
C4A C5A Cl1A . . 119.59(19) ?
C5A C6A C7A . . 119.6(2) ?
C5A C6A H6A . . 120.2 ?
C7A C6A H6A . . 120.2 ?
C2A C7A C6A . . 121.6(2) ?
C2A C7A H7A . . 119.2 ?
C6A C7A H7A . . 119.2 ?
C9A C8A C13A . . 117.9(2) ?
C9A C8A N1A . . 121.6(2) ?
C13A C8A N1A . . 120.5(2) ?
C8A C9A C10A . . 121.1(3) ?
C8A C9A Cl2A . . 120.3(2) ?
C10A C9A Cl2A . . 118.5(2) ?
C11A C10A C9A . . 119.6(3) ?
C11A C10A H10A . . 120.2 ?
C9A C10A H10A . . 120.2 ?
C12A C11A C10A . . 120.6(3) ?
C12A C11A H11A . . 119.7 ?
C10A C11A H11A . . 119.7 ?
C11A C12A C13A . . 119.8(3) ?
C11A C12A H12A . . 120.1 ?
C13A C12A H12A . . 120.1 ?
C12A C13A C8A . . 121.0(3) ?
C12A C13A Cl3A . . 119.6(2) ?
C8A C13A Cl3A . . 119.4(2) ?
C1B N1B C8B . . 121.88(16) ?
C1B N1B H2N . . 122.1(16) ?
C8B N1B H2N . . 116.1(16) ?
O1B C1B N1B . . 120.78(19) ?
O1B C1B C2B . . 121.35(19) ?
N1B C1B C2B . . 117.86(17) ?
C7B C2B C3B . . 118.3(2) ?
C7B C2B C1B . . 124.35(19) ?
C3B C2B C1B . . 117.37(18) ?
C4B C3B C2B . . 120.6(2) ?
C4B C3B H3B . . 119.7 ?
C2B C3B H3B . . 119.7 ?
C5B C4B C3B . . 119.8(2) ?
C5B C4B H4B . . 120.1 ?
C3B C4B H4B . . 120.1 ?
C6B C5B C4B . . 120.6(2) ?
C6B C5B Cl1B . . 120.3(2) ?
C4B C5B Cl1B . . 119.1(2) ?
C5B C6B C7B . . 119.8(2) ?
C5B C6B H6B . . 120.1 ?
C7B C6B H6B . . 120.1 ?
C2B C7B C6B . . 121.0(2) ?
C2B C7B H7B . . 119.5 ?
C6B C7B H7B . . 119.5 ?
C13B C8B C9B . . 117.9(2) ?
C13B C8B N1B . . 121.1(2) ?
C9B C8B N1B . . 121.0(2) ?
C10B C9B C8B . . 121.3(2) ?
C10B C9B Cl2B . . 118.9(2) ?
C8B C9B Cl2B . . 119.77(19) ?
C11B C10B C9B . . 119.3(3) ?
C11B C10B H10B . . 120.4 ?
C9B C10B H10B . . 120.4 ?
C10B C11B C12B . . 121.3(3) ?
C10B C11B H11B . . 119.4 ?
C12B C11B H11B . . 119.4 ?
C11B C12B C13B . . 119.1(3) ?
C11B C12B H12B . . 120.4 ?
C13B C12B H12B . . 120.4 ?
C8B C13B C12B . . 121.2(2) ?
C8B C13B Cl3B . . 119.39(19) ?
C12B C13B Cl3B . . 119.4(2) ?
C1C N1C C8C . . 120.87(16) ?
C1C N1C H3N . . 119.9(15) ?
C8C N1C H3N . . 119.1(15) ?
O1C C1C N1C . . 121.53(19) ?
O1C C1C C2C . . 121.48(17) ?
N1C C1C C2C . . 116.97(16) ?
C3C C2C C7C . . 117.8(2) ?
C3C C2C C1C . . 119.17(18) ?
C7C C2C C1C . . 122.96(18) ?
C4C C3C C2C . . 121.5(2) ?
C4C C3C H3C . . 119.3 ?
C2C C3C H3C . . 119.3 ?
C5C C4C C3C . . 119.5(2) ?
C5C C4C H4C . . 120.3 ?
C3C C4C H4C . . 120.3 ?
C6C C5C C4C . . 120.6(2) ?
C6C C5C Cl1C . . 120.05(18) ?
C4C C5C Cl1C . . 119.30(18) ?
C5C C6C C7C . . 119.7(2) ?
C5C C6C H6C . . 120.1 ?
C7C C6C H6C . . 120.1 ?
C6C C7C C2C . . 120.78(19) ?
C6C C7C H7C . . 119.6 ?
C2C C7C H7C . . 119.6 ?
C9C C8C C13C . . 117.5(2) ?
C9C C8C N1C . . 122.0(2) ?
C13C C8C N1C . . 120.6(2) ?
C8C C9C C10C . . 121.8(2) ?
C8C C9C Cl2C . . 119.87(17) ?
C10C C9C Cl2C . . 118.3(2) ?
C11C C10C C9C . . 118.8(3) ?
C11C C10C H10C . . 120.6 ?
C9C C10C H10C . . 120.6 ?
C10C C11C C12C . . 121.3(3) ?
C10C C11C H11C . . 119.3 ?
C12C C11C H11C . . 119.3 ?
C11C C12C C13C . . 119.0(3) ?
C11C C12C H12C . . 120.5 ?
C13C C12C H12C . . 120.5 ?
C12C C13C C8C . . 121.5(3) ?
C12C C13C Cl3C . . 119.6(2) ?
C8C C13C Cl3C . . 118.9(2) ?
C1D N1D C8D . . 122.27(18) ?
C1D N1D H4N . . 117.4(17) ?
C8D N1D H4N . . 118.5(17) ?
O1D C1D N1D . . 122.2(2) ?
O1D C1D C2D . . 122.27(19) ?
N1D C1D C2D . . 115.48(18) ?
C7D C2D C3D . . 119.0(2) ?
C7D C2D C1D . . 122.9(2) ?
C3D C2D C1D . . 118.1(2) ?
C4D C3D C2D . . 120.7(2) ?
C4D C3D H3D . . 119.6 ?
C2D C3D H3D . . 119.6 ?
C5D C4D C3D . . 119.2(2) ?
C5D C4D H4D . . 120.4 ?
C3D C4D H4D . . 120.4 ?
C4D C5D C6D . . 121.6(2) ?
C4D C5D Cl1D . . 119.2(2) ?
C6D C5D Cl1D . . 119.2(2) ?
C5D C6D C7D . . 119.0(2) ?
C5D C6D H6D . . 120.5 ?
C7D C6D H6D . . 120.5 ?
C2D C7D C6D . . 120.4(2) ?
C2D C7D H7D . . 119.8 ?
C6D C7D H7D . . 119.8 ?
C13D C8D C9D . . 117.7(2) ?
C13D C8D N1D . . 120.7(3) ?
C9D C8D N1D . . 121.6(3) ?
C10D C9D C8D . . 121.6(3) ?
C10D C9D Cl2D . . 119.2(3) ?
C8D C9D Cl2D . . 119.1(2) ?
C9D C10D C11D . . 118.8(3) ?
C9D C10D H10D . . 120(2) ?
C11D C10D H10D . . 121(2) ?
C12D C11D C10D . . 121.6(3) ?
C12D C11D H11D . . 116(2) ?
C10D C11D H11D . . 123(2) ?
C11D C12D C13D . . 119.1(3) ?
C11D C12D H12D . . 127(2) ?
C13D C12D H12D . . 114(2) ?
C12D C13D C8D . . 121.2(3) ?
C12D C13D Cl3D . . 119.4(3) ?
C8D C13D Cl3D . . 119.4(2) ?
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
N1A C1A . 1.334(3) ?
N1A C8A . 1.412(3) ?
N1A H1N . 0.855(16) ?
O1A C1A . 1.223(2) ?
Cl1A C5A . 1.738(2) ?
Cl2A C9A . 1.723(3) ?
Cl3A C13A . 1.715(3) ?
C1A C2A . 1.484(3) ?
C2A C7A . 1.369(3) ?
C2A C3A . 1.382(3) ?
C3A C4A . 1.371(3) ?
C3A H3A . 0.93 ?
C4A C5A . 1.358(3) ?
C4A H4A . 0.93 ?
C5A C6A . 1.358(3) ?
C6A C7A . 1.372(3) ?
C6A H6A . 0.93 ?
C7A H7A . 0.93 ?
C8A C9A . 1.373(3) ?
C8A C13A . 1.397(4) ?
C9A C10A . 1.386(4) ?
C10A C11A . 1.373(4) ?
C10A H10A . 0.93 ?
C11A C12A . 1.358(4) ?
C11A H11A . 0.93 ?
C12A C13A . 1.381(4) ?
C12A H12A . 0.93 ?
N1B C1B . 1.343(3) ?
N1B C8B . 1.408(3) ?
N1B H2N . 0.816(15) ?
O1B C1B . 1.218(2) ?
Cl1B C5B . 1.735(3) ?
Cl2B C9B . 1.718(3) ?
Cl3B C13B . 1.728(3) ?
C1B C2B . 1.489(3) ?
C2B C7B . 1.370(3) ?
C2B C3B . 1.380(3) ?
C3B C4B . 1.373(4) ?
C3B H3B . 0.93 ?
C4B C5B . 1.363(4) ?
C4B H4B . 0.93 ?
C5B C6B . 1.349(4) ?
C6B C7B . 1.375(3) ?
C6B H6B . 0.93 ?
C7B H7B . 0.93 ?
C8B C13B . 1.373(3) ?
C8B C9B . 1.385(3) ?
C9B C10B . 1.375(3) ?
C10B C11B . 1.360(4) ?
C10B H10B . 0.93 ?
C11B C12B . 1.361(4) ?
C11B H11B . 0.93 ?
C12B C13B . 1.385(3) ?
C12B H12B . 0.93 ?
N1C C1C . 1.345(2) ?
N1C C8C . 1.413(3) ?
N1C H3N . 0.842(15) ?
O1C C1C . 1.224(2) ?
Cl1C C5C . 1.736(2) ?
Cl2C C9C . 1.720(3) ?
Cl3C C13C . 1.729(3) ?
C1C C2C . 1.483(3) ?
C2C C3C . 1.376(3) ?
C2C C7C . 1.383(3) ?
C3C C4C . 1.372(3) ?
C3C H3C . 0.93 ?
C4C C5C . 1.363(3) ?
C4C H4C . 0.93 ?
C5C C6C . 1.359(3) ?
C6C C7C . 1.379(3) ?
C6C H6C . 0.93 ?
C7C H7C . 0.93 ?
C8C C9C . 1.381(3) ?
C8C C13C . 1.385(3) ?
C9C C10C . 1.381(3) ?
C10C C11C . 1.366(4) ?
C10C H10C . 0.93 ?
C11C C12C . 1.368(4) ?
C11C H11C . 0.93 ?
C12C C13C . 1.381(4) ?
C12C H12C . 0.93 ?
N1D C1D . 1.339(3) ?
N1D C8D . 1.408(3) ?
N1D H4N . 0.844(16) ?
O1D C1D . 1.222(2) ?
Cl1D C5D . 1.736(2) ?
Cl2D C9D . 1.724(3) ?
Cl3D C13D . 1.725(3) ?
C1D C2D . 1.493(3) ?
C2D C7D . 1.372(3) ?
C2D C3D . 1.381(3) ?
C3D C4D . 1.375(3) ?
C3D H3D . 0.93 ?
C4D C5D . 1.349(4) ?
C4D H4D . 0.93 ?
C5D C6D . 1.373(3) ?
C6D C7D . 1.378(3) ?
C6D H6D . 0.93 ?
C7D H7D . 0.93 ?
C8D C13D . 1.387(4) ?
C8D C9D . 1.392(4) ?
C9D C10D . 1.366(4) ?
C10D C11D . 1.378(5) ?
C10D H10D . 0.96(2) ?
C11D C12D . 1.360(5) ?
C11D H11D . 0.94(2) ?
C12D C13D . 1.382(4) ?
C12D H12D . 0.94(2) ?
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
N1A H1N O1D 4_465 0.855(16) 2.066(17) 2.882(2) 159(2)
N1B H2N O1C 4_565 0.816(15) 2.117(17) 2.880(2) 156(2)
N1C H3N O1B . 0.842(15) 2.054(16) 2.875(2) 165(2)
N1D H4N O1A 1_655 0.844(16) 1.942(19) 2.728(2) 154(2)
C7A H7A O1D 4_465 0.93 2.59 3.489(3) 164
C10C H10C Cl2B 3_656 0.93 2.82 3.599(3) 142
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
C8A N1A C1A O1A . . . . 2.8(4) ?
C8A N1A C1A C2A . . . . -176.4(2) ?
O1A C1A C2A C7A . . . . -172.4(2) ?
N1A C1A C2A C7A . . . . 6.9(4) ?
O1A C1A C2A C3A . . . . 8.9(3) ?
N1A C1A C2A C3A . . . . -171.9(2) ?
C7A C2A C3A C4A . . . . 0.2(4) ?
C1A C2A C3A C4A . . . . 179.0(2) ?
C2A C3A C4A C5A . . . . 0.2(4) ?
C3A C4A C5A C6A . . . . 0.0(4) ?
C3A C4A C5A Cl1A . . . . -179.6(2) ?
C4A C5A C6A C7A . . . . -0.6(4) ?
Cl1A C5A C6A C7A . . . . 179.0(2) ?
C3A C2A C7A C6A . . . . -0.8(4) ?
C1A C2A C7A C6A . . . . -179.5(2) ?
C5A C6A C7A C2A . . . . 1.0(4) ?
C1A N1A C8A C9A . . . . -97.7(3) ?
C1A N1A C8A C13A . . . . 84.6(3) ?
C13A C8A C9A C10A . . . . 1.3(3) ?
N1A C8A C9A C10A . . . . -176.47(19) ?
C13A C8A C9A Cl2A . . . . -179.50(15) ?
N1A C8A C9A Cl2A . . . . 2.8(3) ?
C8A C9A C10A C11A . . . . 0.8(3) ?
Cl2A C9A C10A C11A . . . . -178.44(18) ?
C9A C10A C11A C12A . . . . -1.9(4) ?
C10A C11A C12A C13A . . . . 0.9(4) ?
C11A C12A C13A C8A . . . . 1.2(3) ?
C11A C12A C13A Cl3A . . . . -178.34(18) ?
C9A C8A C13A C12A . . . . -2.3(3) ?
N1A C8A C13A C12A . . . . 175.46(19) ?
C9A C8A C13A Cl3A . . . . 177.28(16) ?
N1A C8A C13A Cl3A . . . . -5.0(3) ?
C8B N1B C1B O1B . . . . 2.0(3) ?
C8B N1B C1B C2B . . . . -176.97(19) ?
O1B C1B C2B C7B . . . . -175.1(2) ?
N1B C1B C2B C7B . . . . 3.9(3) ?
O1B C1B C2B C3B . . . . 3.7(3) ?
N1B C1B C2B C3B . . . . -177.3(2) ?
C7B C2B C3B C4B . . . . 0.9(3) ?
C1B C2B C3B C4B . . . . -178.0(2) ?
C2B C3B C4B C5B . . . . -0.3(4) ?
C3B C4B C5B C6B . . . . -0.7(4) ?
C3B C4B C5B Cl1B . . . . -180.0(2) ?
C4B C5B C6B C7B . . . . 1.1(4) ?
Cl1B C5B C6B C7B . . . . -179.6(2) ?
C3B C2B C7B C6B . . . . -0.5(4) ?
C1B C2B C7B C6B . . . . 178.3(2) ?
C5B C6B C7B C2B . . . . -0.5(4) ?
C1B N1B C8B C13B . . . . -107.0(2) ?
C1B N1B C8B C9B . . . . 73.9(3) ?
C13B C8B C9B C10B . . . . 0.3(3) ?
N1B C8B C9B C10B . . . . 179.4(2) ?
C13B C8B C9B Cl2B . . . . -176.64(16) ?
N1B C8B C9B Cl2B . . . . 2.4(3) ?
C8B C9B C10B C11B . . . . -1.0(4) ?
Cl2B C9B C10B C11B . . . . 175.9(2) ?
C9B C10B C11B C12B . . . . 0.6(4) ?
C10B C11B C12B C13B . . . . 0.6(4) ?
C9B C8B C13B C12B . . . . 0.9(3) ?
N1B C8B C13B C12B . . . . -178.19(19) ?
C9B C8B C13B Cl3B . . . . -179.54(15) ?
N1B C8B C13B Cl3B . . . . 1.4(3) ?
C11B C12B C13B C8B . . . . -1.4(3) ?
C11B C12B C13B Cl3B . . . . 179.1(2) ?
C8C N1C C1C O1C . . . . -7.4(3) ?
C8C N1C C1C C2C . . . . 171.07(18) ?
O1C C1C C2C C3C . . . . -27.0(3) ?
N1C C1C C2C C3C . . . . 154.53(19) ?
O1C C1C C2C C7C . . . . 150.5(2) ?
N1C C1C C2C C7C . . . . -28.0(3) ?
C7C C2C C3C C4C . . . . 1.6(3) ?
C1C C2C C3C C4C . . . . 179.2(2) ?
C2C C3C C4C C5C . . . . -1.6(3) ?
C3C C4C C5C C6C . . . . 0.3(3) ?
C3C C4C C5C Cl1C . . . . 179.65(17) ?
C4C C5C C6C C7C . . . . 1.0(3) ?
Cl1C C5C C6C C7C . . . . -178.36(17) ?
C5C C6C C7C C2C . . . . -1.0(3) ?
C3C C2C C7C C6C . . . . -0.3(3) ?
C1C C2C C7C C6C . . . . -177.8(2) ?
C1C N1C C8C C9C . . . . 91.7(2) ?
C1C N1C C8C C13C . . . . -88.3(2) ?
C13C C8C C9C C10C . . . . 0.5(3) ?
N1C C8C C9C C10C . . . . -179.56(19) ?
C13C C8C C9C Cl2C . . . . -177.83(15) ?
N1C C8C C9C Cl2C . . . . 2.1(3) ?
C8C C9C C10C C11C . . . . 0.4(4) ?
Cl2C C9C C10C C11C . . . . 178.7(2) ?
C9C C10C C11C C12C . . . . -1.0(4) ?
C10C C11C C12C C13C . . . . 0.8(4) ?
C11C C12C C13C C8C . . . . 0.1(4) ?
C11C C12C C13C Cl3C . . . . -178.7(2) ?
C9C C8C C13C C12C . . . . -0.7(3) ?
N1C C8C C13C C12C . . . . 179.31(19) ?
C9C C8C C13C Cl3C . . . . 178.16(16) ?
N1C C8C C13C Cl3C . . . . -1.8(3) ?
C8D N1D C1D O1D . . . . 0.4(4) ?
C8D N1D C1D C2D . . . . -178.3(3) ?
O1D C1D C2D C7D . . . . 147.4(2) ?
N1D C1D C2D C7D . . . . -33.9(3) ?
O1D C1D C2D C3D . . . . -31.2(3) ?
N1D C1D C2D C3D . . . . 147.5(2) ?
C7D C2D C3D C4D . . . . -0.3(3) ?
C1D C2D C3D C4D . . . . 178.4(2) ?
C2D C3D C4D C5D . . . . -0.8(4) ?
C3D C4D C5D C6D . . . . 1.4(4) ?
C3D C4D C5D Cl1D . . . . -178.18(19) ?
C4D C5D C6D C7D . . . . -0.9(4) ?
Cl1D C5D C6D C7D . . . . 178.70(16) ?
C3D C2D C7D C6D . . . . 0.8(3) ?
C1D C2D C7D C6D . . . . -177.8(2) ?
C5D C6D C7D C2D . . . . -0.3(3) ?
C1D N1D C8D C13D . . . . 102.9(3) ?
C1D N1D C8D C9D . . . . -78.9(3) ?
C13D C8D C9D C10D . . . . -2.2(4) ?
N1D C8D C9D C10D . . . . 179.6(2) ?
C13D C8D C9D Cl2D . . . . 177.01(17) ?
N1D C8D C9D Cl2D . . . . -1.2(3) ?
C8D C9D C10D C11D . . . . 1.6(4) ?
Cl2D C9D C10D C11D . . . . -177.6(2) ?
C9D C10D C11D C12D . . . . 0.1(5) ?
C10D C11D C12D C13D . . . . -1.1(5) ?
C11D C12D C13D C8D . . . . 0.4(4) ?
C11D C12D C13D Cl3D . . . . -178.7(2) ?
C9D C8D C13D C12D . . . . 1.2(4) ?
N1D C8D C13D C12D . . . . 179.4(2) ?
C9D C8D C13D Cl3D . . . . -179.74(17) ?
N1D C8D C13D Cl3D . . . . -1.5(3) ?
