#------------------------------------------------------------------------------
#$Date: 2020-06-10 07:56:35 +0300 (Wed, 10 Jun 2020) $
#$Revision: 253058 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/34/2243430.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_2243430
loop_
_publ_author_name
'Atioğlu, Zeliha'
'Akkurt, Mehmet'
'Shikhaliyev, Namiq Q.'
'Mukhtarova, Sevinc H.'
'Suleymanova, Gulnar T.'
'Toze, Flavien A. A.'
_publ_section_title
;
 Crystal structure and Hirshfeld surface analysis of
 4-{2,2-dichloro-1-[(E)-(4-chlorophenyl)diazenyl]ethenyl}-N,N-dimethylaniline
;
_journal_coeditor_code           WM5554
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1033
_journal_page_last               1037
_journal_paper_doi               10.1107/S2056989020007549
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C16 H14 Cl3 N3'
_chemical_formula_sum            'C16 H14 Cl3 N3'
_chemical_formula_weight         354.65
_chemical_name_systematic
4-{2,2-Dichloro-1-[(E)-(4-chlorophenyl)diazenyl]ethenyl}-N,N-dimethylaniline
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/1
_cell_angle_alpha                92.338(2)
_cell_angle_beta                 91.212(2)
_cell_angle_gamma                94.048(2)
_cell_formula_units_Z            6
_cell_length_a                   9.7515(5)
_cell_length_b                   9.8203(5)
_cell_length_c                   26.6696(16)
_cell_measurement_reflns_used    9939
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.55
_cell_measurement_theta_min      2.25
_cell_volume                     2544.7(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
APEX3 (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), OLEX2 (Dolomanov et
al.,  2009)
;
_computing_publication_material
;
PLATON (Spek, 2020), publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEXII PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            40829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_min         2.294
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.539
_exptl_absorpt_correction_T_max  0.946
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.301
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     601
_refine_ls_number_reflns         9634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0500P)²+0.8216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0996
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                6689
_reflns_number_total             9634
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wm5554sup1.cif
_cod_data_source_block           I
_cod_database_code               2243430
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.882
_shelx_estimated_absorpt_t_max   0.953
loop_
_space_group_symop_operation_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_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8482(2) 0.1999(2) 0.93028(8) 0.0452(5) Uani d 1 . .
C C2 0.8218(2) 0.1942(2) 0.87896(8) 0.0546(6) Uani d 1 . .
H H2A 0.774145 0.117448 0.863853 0.066 Uiso calc 1 . .
C C3 0.8656(3) 0.3016(2) 0.85007(9) 0.0572(6) Uani d 1 . .
H H3A 0.848414 0.297623 0.815595 0.069 Uiso calc 1 . .
C C4 0.9351(2) 0.4144(2) 0.87313(9) 0.0524(5) Uani d 1 . .
C C5 0.9607(2) 0.4232(2) 0.92419(9) 0.0539(6) Uani d 1 . .
H H5A 1.006727 0.501099 0.939152 0.065 Uiso calc 1 . .
C C6 0.9173(2) 0.3156(2) 0.95289(8) 0.0511(5) Uani d 1 . .
H H6A 0.934411 0.320453 0.987379 0.061 Uiso calc 1 . .
C C7 0.7902(2) -0.0305(2) 1.02733(8) 0.0475(5) Uani d 1 . .
C C8 0.7076(2) -0.1457(2) 1.00137(8) 0.0445(5) Uani d 1 . .
C C9 0.5679(2) -0.1675(2) 1.00872(9) 0.0534(6) Uani d 1 . .
H H9A 0.526051 -0.111602 1.031902 0.064 Uiso calc 1 . .
C C10 0.4892(2) -0.2699(2) 0.98260(9) 0.0557(6) Uani d 1 . .
H H10A 0.395461 -0.281093 0.988356 0.067 Uiso calc 1 . .
C C11 0.5471(2) -0.3571(2) 0.94773(8) 0.0498(5) Uani d 1 . .
C C12 0.6895(2) -0.3368(2) 0.94155(9) 0.0519(5) Uani d 1 . .
H H12A 0.732733 -0.394639 0.919443 0.062 Uiso calc 1 . .
C C13 0.7660(2) -0.2337(2) 0.96741(8) 0.0507(5) Uani d 1 . .
H H13A 0.859983 -0.222405 0.962023 0.061 Uiso calc 1 . .
C C14 0.8254(2) -0.0283(2) 1.07589(8) 0.0509(5) Uani d 1 . .
C C15 0.3225(3) -0.4714(3) 0.92575(14) 0.0888(9) Uani d 1 . .
H H15A 0.283755 -0.384431 0.924067 0.133 Uiso calc 1 . .
H H15B 0.304255 -0.508699 0.957852 0.133 Uiso calc 1 . .
H H15C 0.281807 -0.532564 0.899690 0.133 Uiso calc 1 . .
C C16 0.5316(3) -0.5541(3) 0.88809(12) 0.0829(8) Uani d 1 . .
H H16A 0.588830 -0.508824 0.864106 0.124 Uiso calc 1 . .
H H16B 0.461159 -0.612219 0.870729 0.124 Uiso calc 1 . .
H H16C 0.586559 -0.608226 0.908655 0.124 Uiso calc 1 . .
N N1 0.79963(19) 0.08299(18) 0.95616(7) 0.0504(4) Uani d 1 . .
N N2 0.83684(19) 0.08700(19) 1.00163(7) 0.0508(4) Uani d 1 . .
N N3 0.4692(2) -0.4541(2) 0.91918(9) 0.0725(6) Uani d 1 . .
Cl Cl1 0.99248(9) 0.55056(8) 0.83780(3) 0.0881(3) Uani d 1 . .
Cl Cl2 0.91333(8) 0.10675(7) 1.10783(2) 0.0745(2) Uani d 1 . .
Cl Cl3 0.78721(7) -0.16465(7) 1.11246(2) 0.06280(17) Uani d 1 . .
C C1A 0.4229(2) 0.1795(2) 0.57132(8) 0.0498(5) Uani d 1 . .
C C2A 0.3627(3) 0.0499(3) 0.56121(9) 0.0640(6) Uani d 1 . .
H H2AA 0.357155 -0.012520 0.586525 0.077 Uiso calc 1 . .
C C3A 0.3104(3) 0.0118(3) 0.51352(11) 0.0718(7) Uani d 1 . .
H H3AA 0.268621 -0.075308 0.506822 0.086 Uiso calc 1 . .
C C4A 0.3211(3) 0.1042(3) 0.47640(9) 0.0646(7) Uani d 1 . .
C C5A 0.3798(3) 0.2340(3) 0.48587(9) 0.0670(7) Uani d 1 . .
H H5AA 0.385665 0.295854 0.460393 0.080 Uiso calc 1 . .
C C6A 0.4299(2) 0.2718(3) 0.53333(9) 0.0593(6) Uani d 1 . .
H H6AA 0.468889 0.360025 0.540009 0.071 Uiso calc 1 . .
C C7A 0.6011(2) 0.3445(2) 0.67585(8) 0.0470(5) Uani d 1 . .
C C8A 0.5983(2) 0.2358(2) 0.71298(8) 0.0454(5) Uani d 1 . .
C C9A 0.4996(3) 0.2286(3) 0.74897(9) 0.0592(6) Uani d 1 . .
H H9AA 0.434165 0.293029 0.749979 0.071 Uiso calc 1 . .
C C10A 0.4954(3) 0.1287(3) 0.78346(9) 0.0607(6) Uani d 1 . .
H H10B 0.426667 0.126346 0.807108 0.073 Uiso calc 1 . .
C C11A 0.5920(2) 0.0304(2) 0.78387(8) 0.0458(5) Uani d 1 . .
C C12A 0.6903(2) 0.0377(2) 0.74676(9) 0.0563(6) Uani d 1 . .
H H12B 0.755564 -0.026818 0.745152 0.068 Uiso calc 1 . .
C C13A 0.6926(2) 0.1388(3) 0.71237(9) 0.0570(6) Uani d 1 . .
H H13B 0.759922 0.141251 0.688154 0.068 Uiso calc 1 . .
C C14A 0.6685(2) 0.4666(2) 0.68521(9) 0.0545(6) Uani d 1 . .
C C15A 0.4881(4) -0.0761(3) 0.85675(12) 0.0900(10) Uani d 1 . .
H H15D 0.496807 0.005235 0.878115 0.135 Uiso calc 1 . .
H H15E 0.500050 -0.154259 0.876465 0.135 Uiso calc 1 . .
H H15F 0.398498 -0.084793 0.840832 0.135 Uiso calc 1 . .
C C16A 0.6869(3) -0.1722(3) 0.81753(12) 0.0777(8) Uani d 1 . .
H H16D 0.778592 -0.131172 0.822915 0.117 Uiso calc 1 . .
H H16E 0.680026 -0.219876 0.785322 0.117 Uiso calc 1 . .
H H16F 0.666243 -0.235499 0.843298 0.117 Uiso calc 1 . .
N N1A 0.47860(19) 0.2058(2) 0.62087(7) 0.0521(5) Uani d 1 . .
N N2A 0.53735(18) 0.3236(2) 0.62771(7) 0.0494(4) Uani d 1 . .
N N3A 0.5912(2) -0.0680(2) 0.81912(7) 0.0600(5) Uani d 1 . .
Cl Cl1A 0.25859(11) 0.05792(10) 0.41636(3) 0.1059(3) Uani d 1 . .
Cl Cl2A 0.67447(7) 0.59912(7) 0.64516(3) 0.07071(19) Uani d 1 . .
Cl Cl3A 0.76185(9) 0.50455(7) 0.73961(3) 0.0824(2) Uani d 1 . .
C C1B 0.8791(2) 0.7795(2) 0.30878(8) 0.0534(5) Uani d 1 . .
C C2B 0.9091(3) 0.8881(3) 0.34212(10) 0.0732(8) Uani d 1 . .
H H2BA 0.907166 0.874525 0.376414 0.088 Uiso calc 1 . .
C C3B 0.9419(3) 1.0168(3) 0.32550(10) 0.0753(8) Uani d 1 . .
H H3BA 0.961150 1.090166 0.348319 0.090 Uiso calc 1 . .
C C4B 0.9458(3) 1.0357(3) 0.27501(9) 0.0580(6) Uani d 1 . .
C C5B 0.9201(3) 0.9284(3) 0.24133(10) 0.0740(8) Uani d 1 . .
H H5BA 0.925262 0.942155 0.207103 0.089 Uiso calc 1 . .
C C6B 0.8865(3) 0.8002(3) 0.25782(9) 0.0710(7) Uani d 1 . .
H H6BA 0.868609 0.727134 0.234787 0.085 Uiso calc 1 . .
C C7B 0.7467(2) 0.4383(2) 0.31889(9) 0.0555(6) Uani d 1 . .
C C8B 0.7881(2) 0.4045(2) 0.37050(9) 0.0496(5) Uani d 1 . .
C C9B 0.9197(2) 0.3708(3) 0.38160(9) 0.0582(6) Uani d 1 . .
H H9BA 0.983240 0.368642 0.356103 0.070 Uiso calc 1 . .
C C10B 0.9597(2) 0.3403(3) 0.42917(10) 0.0609(6) Uani d 1 . .
H H10C 1.048949 0.315983 0.434946 0.073 Uiso calc 1 . .
C C11B 0.8701(2) 0.3447(2) 0.46910(9) 0.0527(5) Uani d 1 . .
C C12B 0.7377(3) 0.3785(3) 0.45733(11) 0.0753(8) Uani d 1 . .
H H12C 0.673596 0.382026 0.482612 0.090 Uiso calc 1 . .
C C13B 0.6991(3) 0.4069(3) 0.40940(11) 0.0752(8) Uani d 1 . .
H H13C 0.609160 0.428491 0.403106 0.090 Uiso calc 1 . .
C C14B 0.6730(3) 0.3507(3) 0.28757(10) 0.0675(7) Uani d 1 . .
C C15B 1.0461(3) 0.2825(4) 0.52857(13) 0.1025(12) Uani d 1 . .
H H15G 1.111103 0.339811 0.510989 0.154 Uiso calc 1 . .
H H15H 1.054616 0.188677 0.518344 0.154 Uiso calc 1 . .
H H15I 1.064191 0.294754 0.564051 0.154 Uiso calc 1 . .
C C16B 0.8219(3) 0.3376(3) 0.55890(11) 0.0845(9) Uani d 1 . .
H H16G 0.785760 0.425916 0.557867 0.127 Uiso calc 1 . .
H H16H 0.873595 0.331524 0.589666 0.127 Uiso calc 1 . .
H H16I 0.747446 0.268088 0.557111 0.127 Uiso calc 1 . .
N N1B 0.8435(2) 0.6513(2) 0.32988(7) 0.0580(5) Uani d 1 . .
N N2B 0.7831(2) 0.5669(2) 0.29885(7) 0.0582(5) Uani d 1 . .
N N3B 0.9100(2) 0.3187(3) 0.51715(8) 0.0759(7) Uani d 1 . .
Cl Cl1B 0.98597(9) 1.19767(8) 0.25356(3) 0.0849(2) Uani d 1 . .
Cl Cl2B 0.62580(10) 0.38856(10) 0.22766(3) 0.1031(3) Uani d 1 . .
Cl Cl3B 0.61794(9) 0.18941(8) 0.30326(3) 0.0901(2) Uani d 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 0.0000 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'
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
C2 C1 C6 . . 119.6(2) ?
C2 C1 N1 . . 115.70(19) ?
C6 C1 N1 . . 124.67(19) ?
C3 C2 C1 . . 120.6(2) ?
C3 C2 H2A . . 119.7 ?
C1 C2 H2A . . 119.7 ?
C4 C3 C2 . . 118.8(2) ?
C4 C3 H3A . . 120.6 ?
C2 C3 H3A . . 120.6 ?
C3 C4 C5 . . 121.6(2) ?
C3 C4 Cl1 . . 119.95(18) ?
C5 C4 Cl1 . . 118.43(18) ?
C4 C5 C6 . . 119.4(2) ?
C4 C5 H5A . . 120.3 ?
C6 C5 H5A . . 120.3 ?
C5 C6 C1 . . 120.0(2) ?
C5 C6 H6A . . 120.0 ?
C1 C6 H6A . . 120.0 ?
C14 C7 N2 . . 115.2(2) ?
C14 C7 C8 . . 123.2(2) ?
N2 C7 C8 . . 121.58(18) ?
C9 C8 C13 . . 117.1(2) ?
C9 C8 C7 . . 121.4(2) ?
C13 C8 C7 . . 121.44(19) ?
C10 C9 C8 . . 121.7(2) ?
C10 C9 H9A . . 119.2 ?
C8 C9 H9A . . 119.2 ?
C9 C10 C11 . . 121.4(2) ?
C9 C10 H10A . . 119.3 ?
C11 C10 H10A . . 119.3 ?
N3 C11 C10 . . 122.3(2) ?
N3 C11 C12 . . 121.2(2) ?
C10 C11 C12 . . 116.5(2) ?
C13 C12 C11 . . 121.3(2) ?
C13 C12 H12A . . 119.3 ?
C11 C12 H12A . . 119.3 ?
C12 C13 C8 . . 121.9(2) ?
C12 C13 H13A . . 119.0 ?
C8 C13 H13A . . 119.0 ?
C7 C14 Cl3 . . 122.13(18) ?
C7 C14 Cl2 . . 124.47(18) ?
Cl3 C14 Cl2 . . 113.40(13) ?
N3 C15 H15A . . 109.5 ?
N3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
N3 C16 H16A . . 109.5 ?
N3 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
N3 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N2 N1 C1 . . 113.53(18) ?
N1 N2 C7 . . 113.61(18) ?
C11 N3 C16 . . 121.5(2) ?
C11 N3 C15 . . 120.0(2) ?
C16 N3 C15 . . 117.8(2) ?
C2A C1A C6A . . 119.2(2) ?
C2A C1A N1A . . 115.7(2) ?
C6A C1A N1A . . 125.0(2) ?
C1A C2A C3A . . 120.4(2) ?
C1A C2A H2AA . . 119.8 ?
C3A C2A H2AA . . 119.8 ?
C4A C3A C2A . . 119.2(3) ?
C4A C3A H3AA . . 120.4 ?
C2A C3A H3AA . . 120.4 ?
C3A C4A C5A . . 121.2(2) ?
C3A C4A Cl1A . . 119.9(2) ?
C5A C4A Cl1A . . 118.9(2) ?
C4A C5A C6A . . 119.4(2) ?
C4A C5A H5AA . . 120.3 ?
C6A C5A H5AA . . 120.3 ?
C5A C6A C1A . . 120.5(2) ?
C5A C6A H6AA . . 119.7 ?
C1A C6A H6AA . . 119.7 ?
C14A C7A N2A . . 115.90(19) ?
C14A C7A C8A . . 121.9(2) ?
N2A C7A C8A . . 122.12(19) ?
C13A C8A C9A . . 117.7(2) ?
C13A C8A C7A . . 121.45(19) ?
C9A C8A C7A . . 120.8(2) ?
C10A C9A C8A . . 121.5(2) ?
C10A C9A H9AA . . 119.2 ?
C8A C9A H9AA . . 119.2 ?
C9A C10A C11A . . 121.5(2) ?
C9A C10A H10B . . 119.3 ?
C11A C10A H10B . . 119.3 ?
N3A C11A C12A . . 121.6(2) ?
N3A C11A C10A . . 122.0(2) ?
C12A C11A C10A . . 116.4(2) ?
C13A C12A C11A . . 121.3(2) ?
C13A C12A H12B . . 119.4 ?
C11A C12A H12B . . 119.4 ?
C8A C13A C12A . . 121.6(2) ?
C8A C13A H13B . . 119.2 ?
C12A C13A H13B . . 119.2 ?
C7A C14A Cl3A . . 122.02(18) ?
C7A C14A Cl2A . . 125.13(18) ?
Cl3A C14A Cl2A . . 112.84(14) ?
N3A C15A H15D . . 109.5 ?
N3A C15A H15E . . 109.5 ?
H15D C15A H15E . . 109.5 ?
N3A C15A H15F . . 109.5 ?
H15D C15A H15F . . 109.5 ?
H15E C15A H15F . . 109.5 ?
N3A C16A H16D . . 109.5 ?
N3A C16A H16E . . 109.5 ?
H16D C16A H16E . . 109.5 ?
N3A C16A H16F . . 109.5 ?
H16D C16A H16F . . 109.5 ?
H16E C16A H16F . . 109.5 ?
N2A N1A C1A . . 113.44(18) ?
N1A N2A C7A . . 112.75(18) ?
C11A N3A C16A . . 121.3(2) ?
C11A N3A C15A . . 121.2(2) ?
C16A N3A C15A . . 117.4(2) ?
C2B C1B C6B . . 119.0(2) ?
C2B C1B N1B . . 116.4(2) ?
C6B C1B N1B . . 124.6(2) ?
C1B C2B C3B . . 120.9(2) ?
C1B C2B H2BA . . 119.6 ?
C3B C2B H2BA . . 119.6 ?
C4B C3B C2B . . 119.2(3) ?
C4B C3B H3BA . . 120.4 ?
C2B C3B H3BA . . 120.4 ?
C5B C4B C3B . . 120.8(2) ?
C5B C4B Cl1B . . 119.55(19) ?
C3B C4B Cl1B . . 119.7(2) ?
C4B C5B C6B . . 120.1(2) ?
C4B C5B H5BA . . 120.0 ?
C6B C5B H5BA . . 120.0 ?
C5B C6B C1B . . 120.0(2) ?
C5B C6B H6BA . . 120.0 ?
C1B C6B H6BA . . 120.0 ?
C14B C7B N2B . . 114.6(2) ?
C14B C7B C8B . . 123.1(2) ?
N2B C7B C8B . . 122.3(2) ?
C13B C8B C9B . . 116.7(2) ?
C13B C8B C7B . . 122.1(2) ?
C9B C8B C7B . . 121.2(2) ?
C10B C9B C8B . . 121.8(2) ?
C10B C9B H9BA . . 119.1 ?
C8B C9B H9BA . . 119.1 ?
C9B C10B C11B . . 121.7(2) ?
C9B C10B H10C . . 119.1 ?
C11B C10B H10C . . 119.1 ?
N3B C11B C12B . . 121.9(2) ?
N3B C11B C10B . . 122.3(2) ?
C12B C11B C10B . . 115.8(2) ?
C13B C12B C11B . . 121.6(2) ?
C13B C12B H12C . . 119.2 ?
C11B C12B H12C . . 119.2 ?
C8B C13B C12B . . 122.3(2) ?
C8B C13B H13C . . 118.8 ?
C12B C13B H13C . . 118.8 ?
C7B C14B Cl3B . . 123.1(2) ?
C7B C14B Cl2B . . 123.4(2) ?
Cl3B C14B Cl2B . . 113.56(15) ?
N3B C15B H15G . . 109.5 ?
N3B C15B H15H . . 109.5 ?
H15G C15B H15H . . 109.5 ?
N3B C15B H15I . . 109.5 ?
H15G C15B H15I . . 109.5 ?
H15H C15B H15I . . 109.5 ?
N3B C16B H16G . . 109.5 ?
N3B C16B H16H . . 109.5 ?
H16G C16B H16H . . 109.5 ?
N3B C16B H16I . . 109.5 ?
H16G C16B H16I . . 109.5 ?
H16H C16B H16I . . 109.5 ?
N2B N1B C1B . . 112.63(19) ?
N1B N2B C7B . . 113.78(19) ?
C11B N3B C15B . . 121.2(2) ?
C11B N3B C16B . . 122.0(2) ?
C15B N3B C16B . . 116.6(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
C1 C2 . 1.386(3) ?
C1 C6 . 1.388(3) ?
C1 N1 . 1.421(3) ?
C2 C3 . 1.380(3) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.373(3) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.377(3) ?
C4 Cl1 . 1.734(2) ?
C5 C6 . 1.378(3) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
C7 C14 . 1.332(3) ?
C7 N2 . 1.418(3) ?
C7 C8 . 1.481(3) ?
C8 C9 . 1.383(3) ?
C8 C13 . 1.385(3) ?
C9 C10 . 1.377(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.393(3) ?
C10 H10A . 0.9300 ?
C11 N3 . 1.370(3) ?
C11 C12 . 1.403(3) ?
C12 C13 . 1.368(3) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C14 Cl3 . 1.713(2) ?
C14 Cl2 . 1.714(2) ?
C15 N3 . 1.445(4) ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
C16 N3 . 1.436(3) ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
N1 N2 . 1.257(2) ?
C1A C2A . 1.378(3) ?
C1A C6A . 1.386(3) ?
C1A N1A . 1.425(3) ?
C2A C3A . 1.387(4) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.370(4) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.371(4) ?
C4A Cl1A . 1.733(3) ?
C5A C6A . 1.374(3) ?
C5A H5AA . 0.9300 ?
C6A H6AA . 0.9300 ?
C7A C14A . 1.338(3) ?
C7A N2A . 1.415(3) ?
C7A C8A . 1.484(3) ?
C8A C13A . 1.370(3) ?
C8A C9A . 1.374(3) ?
C9A C10A . 1.371(3) ?
C9A H9AA . 0.9300 ?
C10A C11A . 1.395(3) ?
C10A H10B . 0.9300 ?
C11A N3A . 1.376(3) ?
C11A C12A . 1.393(3) ?
C12A C13A . 1.378(3) ?
C12A H12B . 0.9300 ?
C13A H13B . 0.9300 ?
C14A Cl3A . 1.710(2) ?
C14A Cl2A . 1.715(2) ?
C15A N3A . 1.436(3) ?
C15A H15D . 0.9600 ?
C15A H15E . 0.9600 ?
C15A H15F . 0.9600 ?
C16A N3A . 1.433(3) ?
C16A H16D . 0.9600 ?
C16A H16E . 0.9600 ?
C16A H16F . 0.9600 ?
N1A N2A . 1.259(3) ?
C1B C2B . 1.372(3) ?
C1B C6B . 1.385(3) ?
C1B N1B . 1.423(3) ?
C2B C3B . 1.375(4) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.368(4) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.362(4) ?
C4B Cl1B . 1.734(2) ?
C5B C6B . 1.370(4) ?
C5B H5BA . 0.9300 ?
C6B H6BA . 0.9300 ?
C7B C14B . 1.335(3) ?
C7B N2B . 1.417(3) ?
C7B C8B . 1.483(3) ?
C8B C13B . 1.367(3) ?
C8B C9B . 1.378(3) ?
C9B C10B . 1.370(3) ?
C9B H9BA . 0.9300 ?
C10B C11B . 1.393(3) ?
C10B H10C . 0.9300 ?
C11B N3B . 1.370(3) ?
C11B C12B . 1.389(3) ?
C12B C13B . 1.370(4) ?
C12B H12C . 0.9300 ?
C13B H13C . 0.9300 ?
C14B Cl3B . 1.707(3) ?
C14B Cl2B . 1.716(3) ?
C15B N3B . 1.428(4) ?
C15B H15G . 0.9600 ?
C15B H15H . 0.9600 ?
C15B H15I . 0.9600 ?
C16B N3B . 1.435(3) ?
C16B H16G . 0.9600 ?
C16B H16H . 0.9600 ?
C16B H16I . 0.9600 ?
N1B N2B . 1.255(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
_geom_hbond_publ_flag
C2 H2A N3A . 0.93 2.68 3.597(3) 167.4 yes
C5B H5BA Cl3 1_564 0.93 2.95 3.703(3) 138.6 yes
C14 Cl3 Cg1 2_757 1.713(2) 3.5462(11) 4.083(2) 95.50(7) yes
C14B Cl3B Cg4 2_656 1.707(3) 3.8493(13) 5.300(3) 141.97(10) yes
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 . . . . 1.1(4) ?
N1 C1 C2 C3 . . . . -179.3(2) ?
C1 C2 C3 C4 . . . . -0.4(4) ?
C2 C3 C4 C5 . . . . -0.6(4) ?
C2 C3 C4 Cl1 . . . . 179.58(19) ?
C3 C4 C5 C6 . . . . 0.9(4) ?
Cl1 C4 C5 C6 . . . . -179.27(18) ?
C4 C5 C6 C1 . . . . -0.2(4) ?
C2 C1 C6 C5 . . . . -0.8(3) ?
N1 C1 C6 C5 . . . . 179.7(2) ?
C14 C7 C8 C9 . . . . 74.0(3) ?
N2 C7 C8 C9 . . . . -105.6(2) ?
C14 C7 C8 C13 . . . . -108.2(3) ?
N2 C7 C8 C13 . . . . 72.2(3) ?
C13 C8 C9 C10 . . . . -1.6(3) ?
C7 C8 C9 C10 . . . . 176.3(2) ?
C8 C9 C10 C11 . . . . 0.5(4) ?
C9 C10 C11 N3 . . . . -175.9(2) ?
C9 C10 C11 C12 . . . . 1.3(3) ?
N3 C11 C12 C13 . . . . 175.3(2) ?
C10 C11 C12 C13 . . . . -2.0(3) ?
C11 C12 C13 C8 . . . . 1.0(3) ?
C9 C8 C13 C12 . . . . 0.9(3) ?
C7 C8 C13 C12 . . . . -177.0(2) ?
N2 C7 C14 Cl3 . . . . -176.21(16) ?
C8 C7 C14 Cl3 . . . . 4.1(3) ?
N2 C7 C14 Cl2 . . . . 3.1(3) ?
C8 C7 C14 Cl2 . . . . -176.55(17) ?
C2 C1 N1 N2 . . . . 173.7(2) ?
C6 C1 N1 N2 . . . . -6.7(3) ?
C1 N1 N2 C7 . . . . -179.12(18) ?
C14 C7 N2 N1 . . . . -178.7(2) ?
C8 C7 N2 N1 . . . . 1.0(3) ?
C10 C11 N3 C16 . . . . -172.1(2) ?
C12 C11 N3 C16 . . . . 10.8(4) ?
C10 C11 N3 C15 . . . . -1.9(4) ?
C12 C11 N3 C15 . . . . -179.0(2) ?
C6A C1A C2A C3A . . . . 0.4(4) ?
N1A C1A C2A C3A . . . . -177.3(2) ?
C1A C2A C3A C4A . . . . 0.9(4) ?
C2A C3A C4A C5A . . . . -1.4(4) ?
C2A C3A C4A Cl1A . . . . 179.1(2) ?
C3A C4A C5A C6A . . . . 0.5(4) ?
Cl1A C4A C5A C6A . . . . -179.9(2) ?
C4A C5A C6A C1A . . . . 0.8(4) ?
C2A C1A C6A C5A . . . . -1.2(4) ?
N1A C1A C6A C5A . . . . 176.3(2) ?
C14A C7A C8A C13A . . . . -92.7(3) ?
N2A C7A C8A C13A . . . . 84.7(3) ?
C14A C7A C8A C9A . . . . 87.8(3) ?
N2A C7A C8A C9A . . . . -94.7(3) ?
C13A C8A C9A C10A . . . . 0.4(4) ?
C7A C8A C9A C10A . . . . 179.9(2) ?
C8A C9A C10A C11A . . . . 0.6(4) ?
C9A C10A C11A N3A . . . . 178.2(2) ?
C9A C10A C11A C12A . . . . -1.4(4) ?
N3A C11A C12A C13A . . . . -178.3(2) ?
C10A C11A C12A C13A . . . . 1.3(4) ?
C9A C8A C13A C12A . . . . -0.5(4) ?
C7A C8A C13A C12A . . . . -180.0(2) ?
C11A C12A C13A C8A . . . . -0.4(4) ?
N2A C7A C14A Cl3A . . . . -175.07(17) ?
C8A C7A C14A Cl3A . . . . 2.5(3) ?
N2A C7A C14A Cl2A . . . . 3.8(3) ?
C8A C7A C14A Cl2A . . . . -178.64(17) ?
C2A C1A N1A N2A . . . . 177.3(2) ?
C6A C1A N1A N2A . . . . -0.3(3) ?
C1A N1A N2A C7A . . . . -175.50(18) ?
C14A C7A N2A N1A . . . . 178.4(2) ?
C8A C7A N2A N1A . . . . 0.8(3) ?
C12A C11A N3A C16A . . . . -3.5(4) ?
C10A C11A N3A C16A . . . . 176.9(3) ?
C12A C11A N3A C15A . . . . -179.0(3) ?
C10A C11A N3A C15A . . . . 1.4(4) ?
C6B C1B C2B C3B . . . . 2.0(4) ?
N1B C1B C2B C3B . . . . -178.7(3) ?
C1B C2B C3B C4B . . . . -0.7(5) ?
C2B C3B C4B C5B . . . . -1.1(4) ?
C2B C3B C4B Cl1B . . . . 179.6(2) ?
C3B C4B C5B C6B . . . . 1.6(4) ?
Cl1B C4B C5B C6B . . . . -179.1(2) ?
C4B C5B C6B C1B . . . . -0.2(4) ?
C2B C1B C6B C5B . . . . -1.6(4) ?
N1B C1B C6B C5B . . . . 179.2(3) ?
C14B C7B C8B C13B . . . . -78.7(3) ?
N2B C7B C8B C13B . . . . 101.5(3) ?
C14B C7B C8B C9B . . . . 102.2(3) ?
N2B C7B C8B C9B . . . . -77.6(3) ?
C13B C8B C9B C10B . . . . 0.4(4) ?
C7B C8B C9B C10B . . . . 179.5(2) ?
C8B C9B C10B C11B . . . . -1.4(4) ?
C9B C10B C11B N3B . . . . -177.9(3) ?
C9B C10B C11B C12B . . . . 1.5(4) ?
N3B C11B C12B C13B . . . . 178.8(3) ?
C10B C11B C12B C13B . . . . -0.6(4) ?
C9B C8B C13B C12B . . . . 0.6(4) ?
C7B C8B C13B C12B . . . . -178.6(3) ?
C11B C12B C13B C8B . . . . -0.4(5) ?
N2B C7B C14B Cl3B . . . . 179.71(18) ?
C8B C7B C14B Cl3B . . . . -0.1(4) ?
N2B C7B C14B Cl2B . . . . 0.3(3) ?
C8B C7B C14B Cl2B . . . . -179.54(19) ?
C2B C1B N1B N2B . . . . 162.2(2) ?
C6B C1B N1B N2B . . . . -18.5(3) ?
C1B N1B N2B C7B . . . . 179.93(19) ?
C14B C7B N2B N1B . . . . 175.0(2) ?
C8B C7B N2B N1B . . . . -5.2(3) ?
C12B C11B N3B C15B . . . . 179.3(3) ?
C10B C11B N3B C15B . . . . -1.3(4) ?
C12B C11B N3B C16B . . . . -6.2(4) ?
C10B C11B N3B C16B . . . . 173.2(3) ?

_cod_database_fobs_code 2243430
