#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/93/2239369.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_2239369
loop_
_publ_author_name
'Yuan, Cai-Xia'
'Yao, Xu-Mei'
'Zhu, Miao-Li'
'Zhu, Hong-Mei'
_publ_section_title
;
4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione
;
_journal_coeditor_code HB7205
_journal_issue 5
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o574
_journal_page_last o575
_journal_paper_doi 10.1107/S1600536814008320
_journal_volume 70
_journal_year 2014
_chemical_formula_iupac 'C11 H11 Cl N4 O S'
_chemical_formula_moiety 'C11 H11 Cl N4 O S'
_chemical_formula_sum 'C11 H11 Cl N4 O S'
_chemical_formula_weight 282.75
_chemical_name_systematic
4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione
_space_group_IT_number 4
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'P 2yb'
_symmetry_space_group_name_H-M 'P 1 21 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-97
_cell_angle_alpha 90.00
_cell_angle_beta 90.997(7)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 6.297(3)
_cell_length_b 16.418(8)
_cell_length_c 12.290(6)
_cell_measurement_reflns_used 1893
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 20.69
_cell_measurement_theta_min 2.48
_cell_volume 1270.4(11)
_computing_cell_refinement 'SAINT (Bruker, 2000)'
_computing_data_collection 'SMART (Bruker, 2000)'
_computing_data_reduction 'SAINT (Bruker, 2000)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature 298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type 'Bruker SMART APEX CCD'
_diffrn_measurement_method '\w 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 0.0600
_diffrn_reflns_av_sigmaI/netI 0.0404
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 14098
_diffrn_reflns_theta_full 25.50
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_min 1.66
_exptl_absorpt_coefficient_mu 0.458
_exptl_absorpt_correction_T_max 0.9345
_exptl_absorpt_correction_T_min 0.9140
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Bruker, 2000)'
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.478
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description block
_exptl_crystal_F_000 584
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.15
_refine_diff_density_max 0.172
_refine_diff_density_min -0.274
_refine_ls_abs_structure_details 'Flack (1983), 2274 Friedel pairs'
_refine_ls_abs_structure_Flack 0.03(10)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.025
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 329
_refine_ls_number_reflns 2451
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.025
_refine_ls_R_factor_all 0.0544
_refine_ls_R_factor_gt 0.0368
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.1830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0764
_refine_ls_wR_factor_ref 0.0841
_reflns_number_gt 1924
_reflns_number_total 2451
_reflns_threshold_expression I>2\s(I)
_iucr_refine_instructions_details
;
TITL I in P2(1)
CELL 0.71073 6.2965 16.4179 12.2896 90.000 90.997 90.000
ZERR 4.00 0.0029 0.0075 0.0057 0.000 0.007 0.000
LATT -1
SYMM -X, 0.5+Y, -Z
SFAC C H N O S Cl
UNIT 44 44 16 4 4 4
MERG 3
OMIT -3.00 51.00
L.S. 4
ACTA
BOND $H
FMAP 2
PLAN 5
CONF
EQIV $2 x+1, y, z
EQIV $1 x-1, y, z
HTAB C4 S2
HTAB C15 S1
HTAB O2 N8
HTAB O1 N4
HTAB N5 S1_$1
HTAB N1 S2_$2
HTAB
MPLA C17 C18 C19 C20 C21 C22
MPLA N5 N6 N7 C12 C13
MPLA C6 C7 C8 C9 C10 C11
MPLA N1 N2 N3 C1 C2
SIZE 0.2 0.2 0.15
WGHT 0.037500 0.183000
FVAR 0.182160
TEMP 25.000
Cl1 6 0.362455 0.608126 1.003311 11.000000 0.079140 0.105430 =
0.042900 0.018130 -0.015160 -0.021880
N1 3 0.255722 0.726695 0.288981 11.000000 0.041270 0.065080 =
0.027210 0.003480 0.008240 -0.004660
AFIX 43
H1 2 0.349364 0.746312 0.246124 11.000000 -1.200000
AFIX 0
N2 3 0.083228 0.682767 0.251988 11.000000 0.042030 0.060670 =
0.028770 -0.002450 0.002590 -0.001980
N3 3 0.089141 0.694825 0.430093 11.000000 0.036140 0.044130 =
0.023960 0.000310 0.007800 0.000280
N4 3 0.005252 0.692137 0.534885 11.000000 0.039970 0.049550 =
0.023960 0.001970 0.007930 0.000550
O1 4 -0.278361 0.724207 0.690736 11.000000 0.048230 0.077640 =
0.037260 0.002420 0.008420 0.009760
AFIX 147
H1A 2 -0.234617 0.725802 0.628314 11.000000 -1.500000
AFIX 0
S1 5 0.445623 0.787629 0.470867 11.000000 0.042890 0.058930 =
0.029290 -0.000760 0.005670 -0.005540
C1 1 0.266167 0.736408 0.396172 11.000000 0.038020 0.045250 =
0.026160 0.006330 0.006620 0.008340
C2 1 -0.017747 0.664576 0.340854 11.000000 0.039020 0.041200 =
0.032740 -0.000470 -0.000340 0.008930
C3 1 -0.215767 0.617482 0.346280 11.000000 0.045870 0.051550 =
0.038740 -0.004200 0.005390 -0.000290
AFIX 23
H3A 2 -0.322637 0.650261 0.381591 11.000000 -1.200000
H3B 2 -0.190916 0.569508 0.390775 11.000000 -1.200000
AFIX 0
C4 1 -0.300285 0.591120 0.235924 11.000000 0.059830 0.045820 =
0.049320 -0.000360 -0.007970 -0.006820
AFIX 137
H4A 2 -0.196415 0.557823 0.200905 11.000000 -1.500000
H4B 2 -0.329447 0.638337 0.192077 11.000000 -1.500000
H4C 2 -0.428672 0.560456 0.244703 11.000000 -1.500000
AFIX 0
C5 1 0.136569 0.671827 0.610256 11.000000 0.043090 0.043120 =
0.031950 0.002190 0.008900 -0.002150
AFIX 43
H5 2 0.274090 0.656957 0.592272 11.000000 -1.200000
AFIX 0
C6 1 0.075647 0.671486 0.723173 11.000000 0.041790 0.041480 =
0.027240 0.000870 0.007070 -0.005790
C7 1 -0.122969 0.698816 0.757843 11.000000 0.048760 0.045620 =
0.029330 -0.001810 0.009960 -0.010100
C8 1 -0.165988 0.700287 0.868364 11.000000 0.054790 0.065700 =
0.036830 -0.004280 0.014450 -0.005410
AFIX 43
H8 2 -0.295597 0.720309 0.891760 11.000000 -1.200000
AFIX 0
C9 1 -0.019373 0.672538 0.943112 11.000000 0.068890 0.071900 =
0.031290 -0.004780 0.016670 -0.024170
AFIX 43
H9 2 -0.050161 0.672991 1.016847 11.000000 -1.200000
AFIX 0
C10 1 0.175946 0.643643 0.908395 11.000000 0.062130 0.060320 =
0.026370 0.004120 -0.003220 -0.020740
C11 1 0.224252 0.644892 0.800509 11.000000 0.047650 0.050470 =
0.038910 -0.001200 0.006970 -0.007390
AFIX 43
H11 2 0.357627 0.627824 0.778493 11.000000 -1.200000
AFIX 0
Cl2 6 -0.304480 0.973112 -0.418891 11.000000 0.064180 0.103310 =
0.033880 0.004120 -0.005350 0.006460
N5 3 -0.214019 0.867264 0.299589 11.000000 0.045440 0.073240 =
0.024650 0.001820 0.009280 -0.001570
AFIX 43
H5A 2 -0.307806 0.848506 0.343033 11.000000 -1.200000
AFIX 0
N6 3 -0.042100 0.911950 0.334692 11.000000 0.045030 0.066190 =
0.030040 -0.005630 0.002580 -0.000350
N7 3 -0.046218 0.896080 0.157945 11.000000 0.039890 0.047730 =
0.020390 0.003580 0.003200 0.005580
N8 3 0.041461 0.895937 0.053750 11.000000 0.044330 0.050170 =
0.026920 0.001680 0.010620 0.002120
O2 4 0.323728 0.855752 -0.100016 11.000000 0.050640 0.082310 =
0.037460 0.004820 0.007670 0.018210
AFIX 147
H2 2 0.285326 0.863159 -0.037374 11.000000 -1.500000
AFIX 0
S2 5 -0.400573 0.802154 0.117759 11.000000 0.044660 0.060550 =
0.030820 0.002570 0.004920 -0.003120
C12 1 -0.223303 0.855321 0.191547 11.000000 0.035640 0.044660 =
0.029240 0.001710 0.005180 0.004950
C13 1 0.058178 0.927734 0.247769 11.000000 0.038780 0.049700 =
0.028440 -0.004390 0.004120 0.007790
C14 1 0.257407 0.976406 0.240131 11.000000 0.051730 0.052640 =
0.042270 -0.001830 0.006170 0.000630
AFIX 23
H14A 2 0.232079 1.023182 0.193468 11.000000 -1.200000
H14B 2 0.366987 0.943372 0.207475 11.000000 -1.200000
AFIX 0
C15 1 0.333860 1.005381 0.351747 11.000000 0.064300 0.058400 =
0.054310 0.001170 -0.010620 -0.013860
AFIX 137
H15A 2 0.354041 0.959272 0.398840 11.000000 -1.500000
H15B 2 0.229817 1.041187 0.382014 11.000000 -1.500000
H15C 2 0.465945 1.033958 0.344785 11.000000 -1.500000
AFIX 0
C16 1 -0.089005 0.912789 -0.023186 11.000000 0.041170 0.037420 =
0.034390 0.006090 0.009420 0.001100
AFIX 43
H16 2 -0.227250 0.927500 -0.006389 11.000000 -1.200000
AFIX 0
C17 1 -0.028173 0.909696 -0.136168 11.000000 0.043910 0.033700 =
0.031490 -0.001760 0.009830 -0.009370
C18 1 0.168967 0.880725 -0.170318 11.000000 0.044760 0.042120 =
0.033500 0.001310 0.007450 0.000930
C19 1 0.211128 0.875961 -0.279930 11.000000 0.051970 0.048400 =
0.038950 -0.008340 0.017270 -0.003770
AFIX 43
H19 2 0.339480 0.854198 -0.302410 11.000000 -1.200000
AFIX 0
C20 1 0.065538 0.903020 -0.356181 11.000000 0.056060 0.051250 =
0.024990 -0.004640 0.010710 -0.003310
AFIX 43
H20 2 0.095540 0.899880 -0.429891 11.000000 -1.200000
AFIX 0
C21 1 -0.126294 0.935028 -0.322798 11.000000 0.050870 0.047330 =
0.028680 0.002180 -0.002780 -0.004840
C22 1 -0.173859 0.936780 -0.214811 11.000000 0.040160 0.051650 =
0.033540 0.000690 0.005170 0.003240
AFIX 43
H22 2 -0.305349 0.956326 -0.193455 11.000000 -1.200000
AFIX 0
HKLF 4
END
;
_cod_data_source_file hb7205sup1.cif
_cod_data_source_block I
_cod_original_cell_volume 1270.2(10)
_cod_original_sg_symbol_Hall 'P 2yb '
_cod_original_sg_symbol_H-M 'P 21 '
_cod_database_code 2239369
_cod_database_fobs_code 2239369
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.3625(2) 0.60813(11) 1.00331(11) 0.0760(5) Uani d . 1 1
N N1 0.2557(6) 0.7267(3) 0.2890(3) 0.0444(10) Uani d . 1 1
H H1 0.3494 0.7463 0.2461 0.053 Uiso calc R 1 1
N N2 0.0832(7) 0.6828(3) 0.2520(3) 0.0438(11) Uani d . 1 1
N N3 0.0891(6) 0.6948(3) 0.4301(3) 0.0347(10) Uani d . 1 1
N N4 0.0053(6) 0.6921(3) 0.5349(3) 0.0377(10) Uani d . 1 1
O O1 -0.2784(6) 0.7242(3) 0.6907(3) 0.0543(11) Uani d . 1 1
H H1A -0.2346 0.7258 0.6283 0.081 Uiso calc R 1 1
S S1 0.44562(18) 0.78763(8) 0.47087(9) 0.0436(3) Uani d . 1 1
C C1 0.2662(7) 0.7364(3) 0.3962(3) 0.0364(11) Uani d . 1 1
C C2 -0.0177(8) 0.6646(3) 0.3409(4) 0.0377(12) Uani d . 1 1
C C3 -0.2158(8) 0.6175(3) 0.3463(4) 0.0453(12) Uani d . 1 1
H H3A -0.3226 0.6503 0.3816 0.054 Uiso calc R 1 1
H H3B -0.1909 0.5695 0.3908 0.054 Uiso calc R 1 1
C C4 -0.3003(8) 0.5911(3) 0.2359(4) 0.0518(14) Uani d . 1 1
H H4A -0.1964 0.5578 0.2009 0.078 Uiso calc R 1 1
H H4B -0.3294 0.6383 0.1921 0.078 Uiso calc R 1 1
H H4C -0.4287 0.5605 0.2447 0.078 Uiso calc R 1 1
C C5 0.1366(8) 0.6718(3) 0.6103(4) 0.0393(13) Uani d . 1 1
H H5 0.2741 0.6570 0.5923 0.047 Uiso calc R 1 1
C C6 0.0756(8) 0.6715(3) 0.7232(4) 0.0368(12) Uani d . 1 1
C C7 -0.1230(8) 0.6988(3) 0.7578(4) 0.0411(13) Uani d . 1 1
C C8 -0.1660(8) 0.7003(3) 0.8684(4) 0.0523(14) Uani d . 1 1
H H8 -0.2956 0.7203 0.8918 0.063 Uiso calc R 1 1
C C9 -0.0194(9) 0.6725(4) 0.9431(4) 0.0572(15) Uani d . 1 1
H H9 -0.0502 0.6730 1.0168 0.069 Uiso calc R 1 1
C C10 0.1759(9) 0.6436(3) 0.9084(4) 0.0497(14) Uani d . 1 1
C C11 0.2243(8) 0.6449(3) 0.8005(4) 0.0456(14) Uani d . 1 1
H H11 0.3576 0.6278 0.7785 0.055 Uiso calc R 1 1
Cl Cl2 -0.3045(2) 0.97311(11) -0.41889(11) 0.0672(5) Uani d . 1 1
N N5 -0.2140(6) 0.8673(3) 0.2996(3) 0.0477(11) Uani d . 1 1
H H5A -0.3078 0.8485 0.3430 0.057 Uiso calc R 1 1
N N6 -0.0421(7) 0.9120(3) 0.3347(3) 0.0471(11) Uani d . 1 1
N N7 -0.0462(6) 0.8961(2) 0.1579(3) 0.0360(10) Uani d . 1 1
N N8 0.0415(6) 0.8959(3) 0.0537(3) 0.0404(10) Uani d . 1 1
O O2 0.3237(5) 0.8558(3) -0.1000(3) 0.0567(10) Uani d . 1 1
H H2 0.2853 0.8632 -0.0374 0.085 Uiso calc R 1 1
S S2 -0.40057(19) 0.80215(8) 0.11776(9) 0.0453(3) Uani d . 1 1
C C12 -0.2233(7) 0.8553(3) 0.1915(4) 0.0365(11) Uani d . 1 1
C C13 0.0582(8) 0.9277(3) 0.2478(4) 0.0389(12) Uani d . 1 1
C C14 0.2574(8) 0.9764(4) 0.2401(4) 0.0488(13) Uani d . 1 1
H H14A 0.2321 1.0232 0.1935 0.059 Uiso calc R 1 1
H H14B 0.3670 0.9434 0.2075 0.059 Uiso calc R 1 1
C C15 0.3339(9) 1.0054(3) 0.3517(4) 0.0591(15) Uani d . 1 1
H H15A 0.3540 0.9593 0.3988 0.089 Uiso calc R 1 1
H H15B 0.2298 1.0412 0.3820 0.089 Uiso calc R 1 1
H H15C 0.4659 1.0340 0.3448 0.089 Uiso calc R 1 1
C C16 -0.0890(8) 0.9128(3) -0.0232(4) 0.0376(13) Uani d . 1 1
H H16 -0.2273 0.9275 -0.0064 0.045 Uiso calc R 1 1
C C17 -0.0282(8) 0.9097(3) -0.1362(4) 0.0363(12) Uani d . 1 1
C C18 0.1690(8) 0.8807(3) -0.1703(4) 0.0400(12) Uani d . 1 1
C C19 0.2111(8) 0.8760(3) -0.2799(4) 0.0463(14) Uani d . 1 1
H H19 0.3395 0.8542 -0.3024 0.056 Uiso calc R 1 1
C C20 0.0655(8) 0.9030(3) -0.3562(4) 0.0440(14) Uani d . 1 1
H H20 0.0955 0.8999 -0.4299 0.053 Uiso calc R 1 1
C C21 -0.1263(9) 0.9350(3) -0.3228(4) 0.0423(13) Uani d . 1 1
C C22 -0.1739(8) 0.9368(3) -0.2148(4) 0.0417(13) Uani d . 1 1
H H22 -0.3053 0.9563 -0.1935 0.050 Uiso calc R 1 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
Cl1 0.0791(11) 0.1054(14) 0.0429(8) -0.0219(10) -0.0152(7) 0.0181(8)
N1 0.041(2) 0.065(3) 0.027(2) -0.005(2) 0.0082(18) 0.003(2)
N2 0.042(3) 0.061(3) 0.029(2) -0.002(2) 0.0026(19) -0.002(2)
N3 0.036(2) 0.044(3) 0.024(2) 0.000(2) 0.0078(17) 0.0003(18)
N4 0.040(2) 0.050(3) 0.024(2) 0.001(2) 0.0079(18) 0.0020(19)
O1 0.048(2) 0.078(3) 0.037(2) 0.010(2) 0.0084(18) 0.002(2)
S1 0.0429(7) 0.0589(8) 0.0293(6) -0.0055(6) 0.0057(5) -0.0008(6)
C1 0.038(3) 0.045(3) 0.026(3) 0.008(2) 0.007(2) 0.006(2)
C2 0.039(3) 0.041(3) 0.033(3) 0.009(2) 0.000(2) 0.000(2)
C3 0.046(3) 0.052(3) 0.039(3) 0.000(3) 0.005(2) -0.004(2)
C4 0.060(3) 0.046(3) 0.049(3) -0.007(3) -0.008(3) 0.000(3)
C5 0.043(3) 0.043(3) 0.032(3) -0.002(2) 0.009(2) 0.002(2)
C6 0.042(3) 0.041(3) 0.027(3) -0.006(2) 0.007(2) 0.001(2)
C7 0.049(3) 0.046(3) 0.029(3) -0.010(3) 0.010(2) -0.002(2)
C8 0.055(3) 0.066(4) 0.037(3) -0.005(3) 0.014(3) -0.004(3)
C9 0.069(4) 0.072(4) 0.031(3) -0.024(3) 0.017(3) -0.005(3)
C10 0.062(4) 0.060(4) 0.026(3) -0.021(3) -0.003(2) 0.004(2)
C11 0.048(3) 0.050(3) 0.039(3) -0.007(3) 0.007(2) -0.001(3)
Cl2 0.0642(9) 0.1033(13) 0.0339(7) 0.0065(9) -0.0054(6) 0.0041(8)
N5 0.045(3) 0.073(3) 0.025(2) -0.002(2) 0.0093(19) 0.002(2)
N6 0.045(3) 0.066(3) 0.030(2) 0.000(2) 0.003(2) -0.006(2)
N7 0.040(2) 0.048(3) 0.020(2) 0.006(2) 0.0032(17) 0.0036(18)
N8 0.044(2) 0.050(3) 0.027(2) 0.002(2) 0.0106(19) 0.0017(19)
O2 0.051(2) 0.082(3) 0.037(2) 0.018(2) 0.0077(17) 0.005(2)
S2 0.0447(7) 0.0605(9) 0.0308(6) -0.0031(7) 0.0049(5) 0.0026(6)
C12 0.036(3) 0.045(3) 0.029(3) 0.005(2) 0.005(2) 0.002(2)
C13 0.039(3) 0.050(3) 0.028(3) 0.008(2) 0.004(2) -0.004(2)
C14 0.052(3) 0.053(3) 0.042(3) 0.001(3) 0.006(2) -0.002(3)
C15 0.064(4) 0.058(4) 0.054(3) -0.014(3) -0.011(3) 0.001(3)
C16 0.041(3) 0.037(3) 0.034(3) 0.001(2) 0.009(2) 0.006(2)
C17 0.044(3) 0.034(3) 0.031(3) -0.009(2) 0.010(2) -0.002(2)
C18 0.045(3) 0.042(3) 0.034(3) 0.001(2) 0.007(2) 0.001(2)
C19 0.052(3) 0.048(3) 0.039(3) -0.004(3) 0.017(3) -0.008(3)
C20 0.056(3) 0.051(3) 0.025(3) -0.003(3) 0.011(2) -0.005(2)
C21 0.051(3) 0.047(3) 0.029(3) -0.005(3) -0.003(2) 0.002(2)
C22 0.040(3) 0.052(3) 0.034(3) 0.003(2) 0.005(2) 0.001(2)
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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C1 N1 N2 114.6(4) n
C1 N1 H1 122.7 ?
N2 N1 H1 122.7 ?
C2 N2 N1 103.7(4) ?
C2 N3 C1 109.0(4) ?
C2 N3 N4 122.5(4) ?
C1 N3 N4 127.8(4) n
C5 N4 N3 115.2(4) ?
C7 O1 H1A 109.5 ?
N1 C1 N3 102.4(4) ?
N1 C1 S1 128.8(4) ?
N3 C1 S1 128.8(3) n
N2 C2 N3 110.3(4) ?
N2 C2 C3 125.7(4) ?
N3 C2 C3 124.0(4) ?
C2 C3 C4 113.3(4) n
C2 C3 H3A 108.9 ?
C4 C3 H3A 108.9 ?
C2 C3 H3B 108.9 ?
C4 C3 H3B 108.9 ?
H3A C3 H3B 107.7 ?
C3 C4 H4A 109.5 ?
C3 C4 H4B 109.5 ?
H4A C4 H4B 109.5 ?
C3 C4 H4C 109.5 ?
H4A C4 H4C 109.5 ?
H4B C4 H4C 109.5 ?
N4 C5 C6 121.2(5) ?
N4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C11 C6 C7 119.0(4) ?
C11 C6 C5 118.0(5) ?
C7 C6 C5 122.9(5) ?
O1 C7 C8 116.4(4) ?
O1 C7 C6 124.1(4) ?
C8 C7 C6 119.5(5) ?
C9 C8 C7 120.6(5) ?
C9 C8 H8 119.7 ?
C7 C8 H8 119.7 ?
C8 C9 C10 119.8(5) ?
C8 C9 H9 120.1 ?
C10 C9 H9 120.1 ?
C11 C10 C9 120.4(5) ?
C11 C10 Cl1 119.8(4) ?
C9 C10 Cl1 119.9(4) ?
C10 C11 C6 120.6(5) ?
C10 C11 H11 119.7 ?
C6 C11 H11 119.7 ?
C12 N5 N6 114.2(4) ?
C12 N5 H5A 122.9 ?
N6 N5 H5A 122.9 ?
C13 N6 N5 104.2(4) ?
C12 N7 C13 108.8(4) ?
C12 N7 N8 127.5(4) ?
C13 N7 N8 122.8(4) ?
C16 N8 N7 114.8(4) ?
C18 O2 H2 109.5 ?
N5 C12 N7 101.8(4) ?
N5 C12 S2 129.0(4) ?
N7 C12 S2 129.1(3) ?
N6 C13 N7 111.0(5) ?
N6 C13 C14 126.2(5) ?
N7 C13 C14 122.8(4) ?
C13 C14 C15 111.3(4) ?
C13 C14 H14A 109.4 ?
C15 C14 H14A 109.4 ?
C13 C14 H14B 109.4 ?
C15 C14 H14B 109.4 ?
H14A C14 H14B 108.0 ?
C14 C15 H15A 109.5 ?
C14 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C14 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
N8 C16 C17 121.8(5) ?
N8 C16 H16 119.1 ?
C17 C16 H16 119.1 ?
C22 C17 C18 118.5(5) ?
C22 C17 C16 118.2(5) ?
C18 C17 C16 123.4(5) ?
O2 C18 C19 117.2(4) ?
O2 C18 C17 122.9(4) ?
C19 C18 C17 119.9(5) ?
C20 C19 C18 120.7(5) ?
C20 C19 H19 119.7 ?
C18 C19 H19 119.7 ?
C19 C20 C21 119.7(5) ?
C19 C20 H20 120.1 ?
C21 C20 H20 120.1 ?
C22 C21 C20 120.2(5) ?
C22 C21 Cl2 120.3(4) ?
C20 C21 Cl2 119.5(4) ?
C21 C22 C17 120.9(5) ?
C21 C22 H22 119.5 ?
C17 C22 H22 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C10 1.741(5) n
N1 C1 1.327(6) n
N1 N2 1.375(6) n
N1 H1 0.8600 ?
N2 C2 1.308(7) n
N3 C2 1.370(6) ?
N3 C1 1.378(6) ?
N3 N4 1.401(5) n
N4 C5 1.275(6) n
O1 C7 1.335(6) n
O1 H1A 0.8200 ?
S1 C1 1.670(5) n
C2 C3 1.470(7) ?
C3 C4 1.512(6) ?
C3 H3A 0.9700 ?
C3 H3B 0.9700 ?
C4 H4A 0.9600 ?
C4 H4B 0.9600 ?
C4 H4C 0.9600 ?
C5 C6 1.446(6) ?
C5 H5 0.9300 ?
C6 C11 1.392(7) ?
C6 C7 1.402(7) ?
C7 C8 1.390(6) ?
C8 C9 1.369(7) ?
C8 H8 0.9300 ?
C9 C10 1.392(8) ?
C9 H9 0.9300 ?
C10 C11 1.366(6) ?
C11 H11 0.9300 ?
Cl2 C21 1.732(5) ?
N5 C12 1.342(6) ?
N5 N6 1.371(5) ?
N5 H5A 0.8600 ?
N6 C13 1.277(7) ?
N7 C12 1.370(6) ?
N7 C13 1.377(6) ?
N7 N8 1.403(5) ?
N8 C16 1.272(6) ?
O2 C18 1.355(5) ?
O2 H2 0.8200 ?
S2 C12 1.672(5) ?
C13 C14 1.492(7) ?
C14 C15 1.522(6) ?
C14 H14A 0.9700 ?
C14 H14B 0.9700 ?
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
C16 C17 1.448(7) ?
C16 H16 0.9300 ?
C17 C22 1.394(7) ?
C17 C18 1.400(7) ?
C18 C19 1.380(7) ?
C19 C20 1.373(7) ?
C19 H19 0.9300 ?
C20 C21 1.386(7) ?
C20 H20 0.9300 ?
C21 C22 1.366(7) ?
C22 H22 0.9300 ?
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 S2 1_655 0.86 2.43 3.287(4) 177 y
N5 H5A S1 1_455 0.86 2.44 3.300(4) 176 y
O1 H1A N4 . 0.82 1.99 2.693(5) 143 y
O2 H2 N8 . 0.82 1.99 2.699(5) 144 y
C15 H15A S1 . 0.96 3.01 3.922(6) 160 y
C4 H4B S2 . 0.96 2.87 3.805(6) 164 y
Cg1 . Cg2 . . . 3.631(3) . ?
Cg3 . Cg4 1_556 . . 3.981(4) . ?
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
C1 N1 N2 C2 0.1(6)
C2 N3 N4 C5 137.3(5)
C1 N3 N4 C5 -53.0(7)
N2 N1 C1 N3 0.8(5)
N2 N1 C1 S1 -178.1(4)
C2 N3 C1 N1 -1.3(5)
N4 N3 C1 N1 -172.1(4)
C2 N3 C1 S1 177.6(4)
N4 N3 C1 S1 6.8(7)
N1 N2 C2 N3 -0.9(5)
N1 N2 C2 C3 180.0(5)
C1 N3 C2 N2 1.5(6)
N4 N3 C2 N2 172.8(4)
C1 N3 C2 C3 -179.4(5)
N4 N3 C2 C3 -8.0(7)
N2 C2 C3 C4 -0.8(7)
N3 C2 C3 C4 -179.8(5)
N3 N4 C5 C6 176.1(4)
N4 C5 C6 C11 177.0(5)
N4 C5 C6 C7 -4.9(8)
C11 C6 C7 O1 -178.7(5)
C5 C6 C7 O1 3.2(8)
C11 C6 C7 C8 1.2(8)
C5 C6 C7 C8 -176.9(5)
O1 C7 C8 C9 177.5(5)
C6 C7 C8 C9 -2.4(8)
C7 C8 C9 C10 0.9(9)
C8 C9 C10 C11 1.8(8)
C8 C9 C10 Cl1 -179.9(4)
C9 C10 C11 C6 -3.0(8)
Cl1 C10 C11 C6 178.7(4)
C7 C6 C11 C10 1.5(8)
C5 C6 C11 C10 179.7(5)
C12 N5 N6 C13 -0.4(6)
C12 N7 N8 C16 52.0(6)
C13 N7 N8 C16 -139.5(5)
N6 N5 C12 N7 -0.6(5)
N6 N5 C12 S2 177.7(4)
C13 N7 C12 N5 1.3(5)
N8 N7 C12 N5 171.1(4)
C13 N7 C12 S2 -177.0(4)
N8 N7 C12 S2 -7.2(7)
N5 N6 C13 N7 1.3(5)
N5 N6 C13 C14 179.0(5)
C12 N7 C13 N6 -1.7(6)
N8 N7 C13 N6 -172.1(4)
C12 N7 C13 C14 -179.5(5)
N8 N7 C13 C14 10.1(7)
N6 C13 C14 C15 0.9(8)
N7 C13 C14 C15 178.4(4)
N7 N8 C16 C17 -175.6(4)
N8 C16 C17 C22 -173.7(5)
N8 C16 C17 C18 6.4(8)
C22 C17 C18 O2 177.7(5)
C16 C17 C18 O2 -2.5(8)
C22 C17 C18 C19 -3.0(8)
C16 C17 C18 C19 176.8(5)
O2 C18 C19 C20 -177.5(5)
C17 C18 C19 C20 3.2(8)
C18 C19 C20 C21 -0.4(8)
C19 C20 C21 C22 -2.5(8)
C19 C20 C21 Cl2 177.2(4)
C20 C21 C22 C17 2.6(8)
Cl2 C21 C22 C17 -177.1(4)
C18 C17 C22 C21 0.2(8)
C16 C17 C22 C21 -179.7(5)