#------------------------------------------------------------------------------
#$Date: 2021-07-10 07:41:05 +0300 (Sat, 10 Jul 2021) $
#$Revision: 267456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243863.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_2243863
loop_
_publ_author_name
'Purandara, H.'
'Foro, Sabine'
'Thimme Gowda, B.'
_publ_section_title
;
Crystal structures of three N-acylhydrazone isomers
;
_journal_coeditor_code MW2177
_journal_issue 8
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first 780
_journal_page_last 784
_journal_paper_doi 10.1107/S2056989021006885
_journal_volume 77
_journal_year 2021
_chemical_formula_iupac 'C15 H13 Cl2 N3 O3 S'
_chemical_formula_moiety 'C15 H13 Cl2 N3 O3 S'
_chemical_formula_sum 'C15 H13 Cl2 N3 O3 S'
_chemical_formula_weight 386.24
_chemical_name_systematic
(E)-4-Chloro-N-{2-[2-(2-chlorobenzylidene)hydrazinyl]-2-oxoethyl}benzenesulfonamide
_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 mixed
_audit_creation_method SHELXL2014/6
_cell_angle_alpha 85.510(10)
_cell_angle_beta 76.920(10)
_cell_angle_gamma 81.040(10)
_cell_formula_units_Z 2
_cell_length_a 7.7426(7)
_cell_length_b 10.4290(10)
_cell_length_c 10.9340(10)
_cell_measurement_reflns_used 2012
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.75
_cell_measurement_theta_min 2.82
_cell_volume 848.64(14)
_computing_cell_refinement
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlis CCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlis RED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
PLATON (Spek, 2020)
;
_computing_publication_material
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014/6 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS2013/1 (Sheldrick, 2008)
;
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur with Sapphire CCD
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0180
_diffrn_reflns_av_unetI/netI 0.0367
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 5699
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 2.815
_diffrn_source 'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.524
_exptl_absorpt_correction_T_max 0.949
_exptl_absorpt_correction_T_min 0.787
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.512
_exptl_crystal_description prism
_exptl_crystal_F_000 396
_exptl_crystal_size_max 0.480
_exptl_crystal_size_mid 0.360
_exptl_crystal_size_min 0.100
_refine_diff_density_max 0.240
_refine_diff_density_min -0.290
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 223
_refine_ls_number_reflns 3417
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.041
_refine_ls_R_factor_all 0.0788
_refine_ls_R_factor_gt 0.0460
_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/[\s^2^(Fo^2^)+(0.0321P)^2^+0.3938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0883
_refine_ls_wR_factor_ref 0.1023
_reflns_number_gt 2359
_reflns_number_total 3417
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file mw2177sup1.cif
_cod_data_source_block I
_cod_database_code 2243863
_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 0.787
_shelx_estimated_absorpt_t_max 0.949
_shelx_hkl_file
;
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9 5 2 253.533 67.6290 2
-9 -5 -2 304.956 64.9009 4
-9 -5 -3 5.71348 35.9584 4
-9 -5 -4 683.460 86.7195 4
-9 -5 -5-74.8275 42.6324 4
-9 -5 -6 581.259 86.6123 1
-9 -5 -7 259.185 66.4364 1
-9 -6 1 169.234 55.0619 6
9 6 0 280.896 79.6608 2
-9 -6 0 163.164 57.0447 6
-9 -6 0 245.280 54.3685 4
9 6 1 315.870 74.1965 2
-9 -6 -1 96.6163 42.0122 4
9 6 2 242.193 70.0535 2
-9 -6 -2 312.601 56.9488 4
9 6 3 278.141 69.7145 2
-9 -6 -3 200.148 45.9431 4
9 6 4 119.652 68.3639 2
-9 -6 -4 86.7131 40.8932 4
-9 -7 0 171.027 59.1528 6
9 7 1 86.0337 63.4148 2
9 7 2 35.5139 63.5178 2
9 7 3-15.5301 67.5690 2
-9 -7 -3-65.4565 35.2720 4
9 7 4 476.631 86.5615 2
-9 -7 -4 334.694 56.5348 4
9 7 6 263.591 80.9834 2
0 0 0 0.00 0.00 0
;
_shelx_hkl_checksum 84417
_shelx_res_file
;
TITL GSH22 P-1
CELL 0.71073 7.74260 10.42900 10.93400 85.51000 76.92000 81.04000
ZERR 2 0.00070 0.00100 0.00100 0.01000 0.01000 0.01000
LATT 1
SFAC C H N O CL S
UNIT 30 26 6 6 4 2
PLAN 30
FMAP 2
SHEL 11 0.8
SIZE 0.48 0.36 0.10
L.S. 4
MPLA 5 S1 N1 C7 C8 O3
MPLA 6 C1 C2 C3 C4 C5 C6
MPLA 6 C10 C11 C12 C13 C14 C15
MPLA 5 C9 N3 N2 C8 O3
BOND $H
DFIX 0.86 0.02 N1 H1N N2 H2N
HTAB N1 O3_$1
HTAB N2 O3_$2
EQIV $1 -x+1, -y+1, -z+1
EQIV $2 -x+2, -y+1, -z+1
CONF
ACTA
WGHT 0.032100 0.393800
FVAR 3.44494
C1 1 0.174632 0.607634 0.844023 11.00000 0.04758 0.04543 =
0.04973 0.00055 -0.00620 -0.00402
C2 1 0.189749 0.719192 0.898519 11.00000 0.06855 0.06239 =
0.07131 -0.01578 -0.00023 -0.01285
AFIX 43
H2 2 0.302302 0.739941 0.898500 11.00000 -1.20000
AFIX 0
C3 1 0.037824 0.799722 0.952928 11.00000 0.10473 0.06167 =
0.07124 -0.01378 0.01069 0.00444
AFIX 43
H3 2 0.047323 0.875608 0.988753 11.00000 -1.20000
AFIX 0
C4 1 -0.127030 0.767470 0.953974 11.00000 0.07868 0.07737 =
0.05644 0.01207 0.01224 0.02641
C5 1 -0.144801 0.655081 0.904154 11.00000 0.04739 0.10475 =
0.06437 0.01928 -0.00396 0.00337
AFIX 43
H5 2 -0.257889 0.633020 0.908275 11.00000 -1.20000
AFIX 0
C6 1 0.007932 0.574167 0.847293 11.00000 0.05044 0.06631 =
0.05971 0.00427 -0.01043 -0.00825
AFIX 43
H6 2 -0.002160 0.498231 0.811810 11.00000 -1.20000
AFIX 0
C7 1 0.559739 0.672653 0.604585 11.00000 0.03801 0.04036 =
0.07585 -0.01509 -0.00398 -0.00496
AFIX 23
H7A 2 0.550411 0.719822 0.679363 11.00000 -1.20000
H7B 2 0.537579 0.735668 0.537807 11.00000 -1.20000
AFIX 0
C8 1 0.748342 0.600211 0.566963 11.00000 0.03743 0.03244 =
0.04501 -0.00287 -0.00756 -0.00410
C9 1 0.973754 0.848446 0.618386 11.00000 0.03601 0.03329 =
0.05132 -0.00325 -0.00788 -0.00354
AFIX 43
H9 2 1.090999 0.807426 0.594299 11.00000 -1.20000
AFIX 0
C10 1 0.936810 0.981591 0.662185 11.00000 0.03917 0.02890 =
0.04517 -0.00178 -0.00775 -0.00350
C11 1 1.070516 1.051504 0.675287 11.00000 0.04019 0.03712 =
0.05254 -0.00209 -0.01134 -0.00631
C12 1 1.032192 1.177692 0.714938 11.00000 0.06044 0.03966 =
0.06897 -0.00704 -0.01785 -0.01643
AFIX 43
H12 2 1.123864 1.221704 0.724027 11.00000 -1.20000
AFIX 0
C13 1 0.857249 1.237402 0.740776 11.00000 0.07496 0.03224 =
0.07708 -0.01237 -0.01530 -0.00291
AFIX 43
H13 2 0.830620 1.322359 0.766855 11.00000 -1.20000
AFIX 0
C14 1 0.721258 1.171707 0.728135 11.00000 0.05083 0.04143 =
0.08570 -0.01241 -0.00683 0.00513
AFIX 43
H14 2 0.603184 1.212382 0.745156 11.00000 -1.20000
AFIX 0
C15 1 0.760995 1.045696 0.690224 11.00000 0.04138 0.03907 =
0.07372 -0.00721 -0.00964 -0.00583
AFIX 43
H15 2 0.668121 1.001930 0.683057 11.00000 -1.20000
AFIX 0
N1 3 0.424120 0.587240 0.629228 11.00000 0.04121 0.06168 =
0.05758 -0.01711 -0.00386 -0.01814
H1N 2 0.383150 0.568853 0.568855 11.00000 -1.20000
N2 3 0.882042 0.665602 0.571555 11.00000 0.03396 0.03047 =
0.06005 -0.00926 -0.00528 -0.00331
H2N 2 0.989721 0.630876 0.544024 11.00000 -1.20000
N3 3 0.843016 0.790183 0.613922 11.00000 0.04048 0.02984 =
0.05289 -0.00566 -0.00856 -0.00516
O1 4 0.508989 0.513143 0.828194 11.00000 0.05769 0.08224 =
0.08955 -0.00947 -0.03135 0.00290
O2 4 0.318007 0.391496 0.738780 11.00000 0.06959 0.03843 =
0.10988 -0.01163 -0.01317 -0.00786
O3 4 0.777753 0.487845 0.531162 11.00000 0.03933 0.03417 =
0.07249 -0.01528 -0.01153 -0.00302
CL1 5 -0.317362 0.872094 1.018930 11.00000 0.11775 0.14002 =
0.10469 0.01513 0.03318 0.06949
CL2 5 1.295021 0.981931 0.639264 11.00000 0.03913 0.06168 =
0.10916 -0.01815 -0.01808 -0.00662
S1 6 0.369388 0.511591 0.762644 11.00000 0.04276 0.04325 =
0.07219 -0.00925 -0.01134 -0.00285
HKLF 4
REM GSH22 P-1
REM R1 = 0.0460 for 2359 Fo > 4sig(Fo) and 0.0788 for all 3417 data
REM 223 parameters refined using 2 restraints
END
WGHT 0.0317 0.3940
REM Highest difference peak 0.240, deepest hole -0.290, 1-sigma level 0.051
Q1 1 0.2638 0.5636 0.8066 11.00000 0.05 0.24
Q2 1 1.2329 0.9732 0.7567 11.00000 0.05 0.20
Q3 1 -0.3221 0.8852 1.0574 11.00000 0.05 0.20
Q4 1 0.5412 0.6800 0.7557 11.00000 0.05 0.19
Q5 1 1.1130 1.1341 0.5506 11.00000 0.05 0.18
Q6 1 0.4517 0.5150 0.6643 11.00000 0.05 0.18
Q7 1 0.2332 0.4325 0.7029 11.00000 0.05 0.17
Q8 1 -0.3779 0.8439 0.9566 11.00000 0.05 0.17
Q9 1 0.1218 0.8495 0.8108 11.00000 0.05 0.16
Q10 1 0.8581 1.0258 0.6477 11.00000 0.05 0.15
Q11 1 0.3228 0.9478 0.8421 11.00000 0.05 0.15
Q12 1 0.7342 0.7809 0.6640 11.00000 0.05 0.15
Q13 1 0.7333 1.0972 0.5229 11.00000 0.05 0.15
Q14 1 0.8212 0.9016 0.7703 11.00000 0.05 0.15
Q15 1 0.1749 0.9432 0.8578 11.00000 0.05 0.15
Q16 1 1.3791 0.9611 0.5337 11.00000 0.05 0.15
Q17 1 1.3007 0.9822 0.8253 11.00000 0.05 0.15
Q18 1 0.6553 0.6362 0.6020 11.00000 0.05 0.15
Q19 1 0.6747 0.4707 0.5817 11.00000 0.05 0.15
Q20 1 0.3431 0.6065 0.6791 11.00000 0.05 0.14
Q21 1 0.6152 1.0765 0.5458 11.00000 0.05 0.14
Q22 1 0.4898 0.6219 0.6275 11.00000 0.05 0.14
Q23 1 -0.0331 0.7432 1.0984 11.00000 0.05 0.14
Q24 1 0.1076 0.6000 0.7969 11.00000 0.05 0.14
Q25 1 -0.1367 0.7371 0.7983 11.00000 0.05 0.14
Q26 1 0.6699 1.2217 0.5783 11.00000 0.05 0.14
Q27 1 0.1073 0.6151 0.7069 11.00000 0.05 0.14
Q28 1 0.4672 0.4789 0.5821 11.00000 0.05 0.14
Q29 1 0.1219 0.6572 1.0455 11.00000 0.05 0.14
Q30 1 1.1783 1.0566 0.8149 11.00000 0.05 0.13
;
_shelx_res_checksum 25175
_shelxl_version_number 2014/6
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 0.1746(3) 0.6076(2) 0.8440(2) 0.0487(6) Uani d 1 . .
C C2 0.1897(4) 0.7192(3) 0.8985(3) 0.0687(8) Uani d 1 . .
H H2 0.3023 0.7399 0.8985 0.082 Uiso calc 1 . .
C C3 0.0378(5) 0.7997(3) 0.9529(3) 0.0852(11) Uani d 1 . .
H H3 0.0473 0.8756 0.9888 0.102 Uiso calc 1 . .
C C4 -0.1270(5) 0.7675(4) 0.9540(3) 0.0801(11) Uani d 1 . .
C C5 -0.1448(4) 0.6551(4) 0.9042(3) 0.0763(10) Uani d 1 . .
H H5 -0.2579 0.6330 0.9083 0.092 Uiso calc 1 . .
C C6 0.0079(4) 0.5742(3) 0.8473(3) 0.0595(7) Uani d 1 . .
H H6 -0.0022 0.4982 0.8118 0.071 Uiso calc 1 . .
C C7 0.5597(3) 0.6727(2) 0.6046(3) 0.0521(7) Uani d 1 . .
H H7A 0.5504 0.7198 0.6794 0.063 Uiso calc 1 . .
H H7B 0.5376 0.7357 0.5378 0.063 Uiso calc 1 . .
C C8 0.7483(3) 0.6002(2) 0.5670(2) 0.0386(5) Uani d 1 . .
C C9 0.9738(3) 0.8484(2) 0.6184(2) 0.0405(6) Uani d 1 . .
H H9 1.0910 0.8074 0.5943 0.049 Uiso calc 1 . .
C C10 0.9368(3) 0.9816(2) 0.6622(2) 0.0381(5) Uani d 1 . .
C C11 1.0705(3) 1.0515(2) 0.6753(2) 0.0430(6) Uani d 1 . .
C C12 1.0322(4) 1.1777(2) 0.7149(3) 0.0545(7) Uani d 1 . .
H H12 1.1239 1.2217 0.7240 0.065 Uiso calc 1 . .
C C13 0.8572(4) 1.2374(3) 0.7408(3) 0.0616(8) Uani d 1 . .
H H13 0.8306 1.3224 0.7669 0.074 Uiso calc 1 . .
C C14 0.7213(4) 1.1717(3) 0.7281(3) 0.0614(8) Uani d 1 . .
H H14 0.6032 1.2124 0.7452 0.074 Uiso calc 1 . .
C C15 0.7610(3) 1.0457(2) 0.6902(3) 0.0516(7) Uani d 1 . .
H H15 0.6681 1.0019 0.6831 0.062 Uiso calc 1 . .
N N1 0.4241(3) 0.5872(2) 0.6292(2) 0.0526(6) Uani d 1 . .
H H1N 0.383(3) 0.569(3) 0.569(2) 0.063 Uiso d 1 . .
N N2 0.8820(3) 0.66560(18) 0.5716(2) 0.0420(5) Uani d 1 . .
H H2N 0.990(2) 0.631(2) 0.544(2) 0.050 Uiso d 1 . .
N N3 0.8430(2) 0.79018(18) 0.61392(19) 0.0411(5) Uani d 1 . .
O O1 0.5090(3) 0.5131(2) 0.8282(2) 0.0751(6) Uani d 1 . .
O O2 0.3180(3) 0.39150(17) 0.7388(2) 0.0732(6) Uani d 1 . .
O O3 0.7778(2) 0.48784(15) 0.53116(17) 0.0483(4) Uani d 1 . .
Cl Cl1 -0.31736(16) 0.87209(13) 1.01893(11) 0.1407(6) Uani d 1 . .
Cl Cl2 1.29502(9) 0.98193(7) 0.63926(8) 0.0690(3) Uani d 1 . .
S S1 0.36939(9) 0.51159(7) 0.76264(7) 0.0529(2) Uani d 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
C1 0.0476(15) 0.0454(15) 0.0497(16) -0.0040(12) -0.0062(12) 0.0005(12)
C2 0.0685(19) 0.062(2) 0.071(2) -0.0128(16) -0.0002(16) -0.0158(17)
C3 0.105(3) 0.062(2) 0.071(2) 0.004(2) 0.011(2) -0.0138(18)
C4 0.079(2) 0.077(2) 0.056(2) 0.026(2) 0.0122(17) 0.0121(18)
C5 0.0474(17) 0.105(3) 0.064(2) 0.0034(18) -0.0040(15) 0.019(2)
C6 0.0504(16) 0.0663(19) 0.0597(18) -0.0082(14) -0.0104(14) 0.0043(15)
C7 0.0380(13) 0.0404(15) 0.0759(19) -0.0050(11) -0.0040(13) -0.0151(13)
C8 0.0374(12) 0.0324(13) 0.0450(14) -0.0041(10) -0.0076(11) -0.0029(11)
C9 0.0360(12) 0.0333(13) 0.0513(15) -0.0035(10) -0.0079(11) -0.0032(11)
C10 0.0392(12) 0.0289(12) 0.0452(14) -0.0035(10) -0.0077(11) -0.0018(11)
C11 0.0402(13) 0.0371(13) 0.0525(16) -0.0063(10) -0.0113(11) -0.0021(12)
C12 0.0604(17) 0.0397(15) 0.0690(19) -0.0164(13) -0.0179(14) -0.0070(14)
C13 0.075(2) 0.0322(14) 0.077(2) -0.0029(14) -0.0153(16) -0.0124(14)
C14 0.0508(16) 0.0414(16) 0.086(2) 0.0051(13) -0.0068(15) -0.0124(15)
C15 0.0414(14) 0.0391(14) 0.0737(19) -0.0058(11) -0.0096(13) -0.0072(13)
N1 0.0412(12) 0.0617(15) 0.0576(15) -0.0181(11) -0.0039(10) -0.0171(12)
N2 0.0340(10) 0.0305(11) 0.0600(14) -0.0033(9) -0.0053(10) -0.0093(10)
N3 0.0405(11) 0.0298(10) 0.0529(13) -0.0052(9) -0.0086(9) -0.0057(9)
O1 0.0577(12) 0.0822(15) 0.0895(16) 0.0029(11) -0.0313(11) -0.0095(13)
O2 0.0696(13) 0.0384(11) 0.1099(18) -0.0079(10) -0.0132(12) -0.0116(11)
O3 0.0393(9) 0.0342(9) 0.0725(12) -0.0030(7) -0.0115(8) -0.0153(9)
Cl1 0.1177(9) 0.1400(10) 0.1047(8) 0.0695(8) 0.0332(7) 0.0151(7)
Cl2 0.0391(4) 0.0617(5) 0.1092(7) -0.0066(3) -0.0181(4) -0.0182(4)
S1 0.0428(4) 0.0433(4) 0.0722(5) -0.0029(3) -0.0113(3) -0.0093(3)
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'
S S 0.1246 0.1234 '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 . . 120.3(3) ?
C2 C1 S1 . . 119.8(2) ?
C6 C1 S1 . . 119.8(2) ?
C3 C2 C1 . . 119.9(3) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.6(3) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 121.4(3) ?
C3 C4 Cl1 . . 119.1(3) ?
C5 C4 Cl1 . . 119.5(3) ?
C4 C5 C6 . . 119.4(3) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C1 C6 C5 . . 119.4(3) ?
C1 C6 H6 . . 120.3 ?
C5 C6 H6 . . 120.3 ?
N1 C7 C8 . . 112.8(2) ?
N1 C7 H7A . . 109.0 ?
C8 C7 H7A . . 109.0 ?
N1 C7 H7B . . 109.0 ?
C8 C7 H7B . . 109.0 ?
H7A C7 H7B . . 107.8 ?
O3 C8 N2 . . 121.5(2) ?
O3 C8 C7 . . 122.1(2) ?
N2 C8 C7 . . 116.5(2) ?
N3 C9 C10 . . 119.0(2) ?
N3 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C15 . . 116.6(2) ?
C11 C10 C9 . . 123.2(2) ?
C15 C10 C9 . . 120.2(2) ?
C12 C11 C10 . . 122.1(2) ?
C12 C11 Cl2 . . 117.61(19) ?
C10 C11 Cl2 . . 120.32(18) ?
C13 C12 C11 . . 119.4(2) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.2(2) ?
C12 C13 H13 . . 119.9 ?
C14 C13 H13 . . 119.9 ?
C15 C14 C13 . . 119.7(3) ?
C15 C14 H14 . . 120.1 ?
C13 C14 H14 . . 120.1 ?
C14 C15 C10 . . 121.9(2) ?
C14 C15 H15 . . 119.0 ?
C10 C15 H15 . . 119.0 ?
C7 N1 S1 . . 122.21(19) ?
C7 N1 H1N . . 119(2) ?
S1 N1 H1N . . 119(2) ?
C8 N2 N3 . . 119.52(19) ?
C8 N2 H2N . . 119.0(17) ?
N3 N2 H2N . . 121.4(17) ?
C9 N3 N2 . . 117.61(19) ?
O1 S1 O2 . . 120.84(13) ?
O1 S1 N1 . . 107.43(13) ?
O2 S1 N1 . . 107.08(12) ?
O1 S1 C1 . . 107.99(13) ?
O2 S1 C1 . . 107.31(12) ?
N1 S1 C1 . . 105.16(12) ?
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 . 1.380(4) ?
C1 C6 . 1.381(4) ?
C1 S1 . 1.769(3) ?
C2 C3 . 1.377(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.367(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.369(5) ?
C4 Cl1 . 1.736(3) ?
C5 C6 . 1.391(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.447(3) ?
C7 C8 . 1.518(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 O3 . 1.236(3) ?
C8 N2 . 1.337(3) ?
C9 N3 . 1.271(3) ?
C9 C10 . 1.469(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.394(3) ?
C10 C15 . 1.398(3) ?
C11 C12 . 1.385(3) ?
C11 Cl2 . 1.745(2) ?
C12 C13 . 1.376(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(4) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.377(3) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
N1 S1 . 1.604(2) ?
N1 H1N . 0.841(16) ?
N2 N3 . 1.379(3) ?
N2 H2N . 0.852(16) ?
O1 S1 . 1.4283(19) ?
O2 S1 . 1.4312(19) ?
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
N1 H1N O3 2_666 0.841(16) 2.011(18) 2.823(3) 162(3)
N2 H2N O3 2_766 0.852(16) 2.060(17) 2.897(2) 167(2)
C12 H12 O2 1_665 0.93 2.53 3.439(3) 165.5
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 . . . . -2.1(4) ?
S1 C1 C2 C3 . . . . 174.7(2) ?
C1 C2 C3 C4 . . . . 0.9(5) ?
C2 C3 C4 C5 . . . . 1.3(5) ?
C2 C3 C4 Cl1 . . . . -178.2(2) ?
C3 C4 C5 C6 . . . . -2.3(5) ?
Cl1 C4 C5 C6 . . . . 177.2(2) ?
C2 C1 C6 C5 . . . . 1.1(4) ?
S1 C1 C6 C5 . . . . -175.7(2) ?
C4 C5 C6 C1 . . . . 1.1(4) ?
N1 C7 C8 O3 . . . . 17.0(4) ?
N1 C7 C8 N2 . . . . -164.6(2) ?
N3 C9 C10 C11 . . . . 177.3(2) ?
N3 C9 C10 C15 . . . . -4.3(4) ?
C15 C10 C11 C12 . . . . 0.5(4) ?
C9 C10 C11 C12 . . . . 179.0(2) ?
C15 C10 C11 Cl2 . . . . -178.54(19) ?
C9 C10 C11 Cl2 . . . . 0.0(3) ?
C10 C11 C12 C13 . . . . -0.9(4) ?
Cl2 C11 C12 C13 . . . . 178.1(2) ?
C11 C12 C13 C14 . . . . 0.5(4) ?
C12 C13 C14 C15 . . . . 0.4(5) ?
C13 C14 C15 C10 . . . . -0.8(4) ?
C11 C10 C15 C14 . . . . 0.4(4) ?
C9 C10 C15 C14 . . . . -178.1(3) ?
C8 C7 N1 S1 . . . . 83.6(3) ?
O3 C8 N2 N3 . . . . -179.0(2) ?
C7 C8 N2 N3 . . . . 2.6(3) ?
C10 C9 N3 N2 . . . . 179.6(2) ?
C8 N2 N3 C9 . . . . 179.1(2) ?
C7 N1 S1 O1 . . . . -17.3(2) ?
C7 N1 S1 O2 . . . . -148.5(2) ?
C7 N1 S1 C1 . . . . 97.6(2) ?
C2 C1 S1 O1 . . . . 36.9(3) ?
C6 C1 S1 O1 . . . . -146.3(2) ?
C2 C1 S1 O2 . . . . 168.7(2) ?
C6 C1 S1 O2 . . . . -14.6(3) ?
C2 C1 S1 N1 . . . . -77.6(2) ?
C6 C1 S1 N1 . . . . 99.2(2) ?
_cod_database_fobs_code 2243863