#------------------------------------------------------------------------------
#$Date: 2021-07-10 07:41:05 +0300 (Sat, 10 Jul 2021) $
#$Revision: 267456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/38/2243865.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_2243865
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-(4-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
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL2014/6
_cell_angle_alpha 74.980(10)
_cell_angle_beta 87.110(10)
_cell_angle_gamma 75.340(10)
_cell_formula_units_Z 2
_cell_length_a 6.7234(9)
_cell_length_b 10.2810(10)
_cell_length_c 13.611(2)
_cell_measurement_reflns_used 1746
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.93
_cell_measurement_theta_min 2.92
_cell_volume 879.0(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.998
_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 0.0187
_diffrn_reflns_av_unetI/netI 0.0292
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 5737
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.372
_diffrn_reflns_theta_min 2.926
_diffrn_source 'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu 0.506
_exptl_absorpt_correction_T_max 0.9055
_exptl_absorpt_correction_T_min 0.8005
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED, Oxford Diffraction, 2009)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.459
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description rod
_exptl_crystal_F_000 396
_exptl_crystal_size_max 0.460
_exptl_crystal_size_mid 0.420
_exptl_crystal_size_min 0.200
_refine_diff_density_max 0.334
_refine_diff_density_min -0.299
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 223
_refine_ls_number_reflns 3598
_refine_ls_number_restraints 2
_refine_ls_restrained_S_all 1.036
_refine_ls_R_factor_all 0.0731
_refine_ls_R_factor_gt 0.0480
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0407P)^2^+0.5495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1059
_refine_ls_wR_factor_ref 0.1198
_reflns_number_gt 2600
_reflns_number_total 3598
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file mw2177sup1.cif
_cod_data_source_block III
_cod_database_code 2243865
_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 0.801
_shelx_estimated_absorpt_t_max 0.906
_shelx_hkl_file
;
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;
_shelx_hkl_checksum 25742
_shelx_res_file
;
TITL GSH10 P-1
III.res
created by SHELXL-2018/3 at 09:46:34 on 02-Jul-2021
CELL 0.71073 6.72340 10.28100 13.61100 74.98000 87.11000 75.34000
ZERR 2 0.00090 0.00100 0.00200 0.01000 0.01000 0.01000
LATT 1
SFAC C H CL N O S
UNIT 30 26 4 6 6 2
LIST 4
PLAN 30
FMAP 2
SHEL 14 0.8
SIZE 0.46 0.42 0.20
L.S. 14
OMIT -1 -1 3
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
DFIX 0.86 0.02 N1 H1N N2 H2N
BOND $H
HTAB N1 O2_$1
HTAB N2 O3_$2
EQIV $1 -x-1, -y+2, -z
EQIV $2 -x, -y+1, -z
HTAB
CONF
ACTA
WGHT 0.040700 0.549500
FVAR 6.42182
CL1 3 -0.753700 0.815344 0.504743 11.00000 0.12250 0.17211 =
0.08620 -0.01301 0.03749 -0.05627
CL2 3 1.202476 0.427105 0.398379 11.00000 0.07373 0.18479 =
0.07794 -0.01849 -0.02473 -0.04389
S1 6 -0.279688 1.019926 0.113212 11.00000 0.04598 0.04783 =
0.05652 -0.01812 -0.00338 -0.01235
O1 5 -0.103087 1.054614 0.142900 11.00000 0.05160 0.06290 =
0.07995 -0.03030 -0.00164 -0.02247
O2 5 -0.424070 1.121322 0.041192 11.00000 0.06161 0.05183 =
0.06946 -0.00761 -0.01113 -0.00973
O3 5 -0.144138 0.664400 0.003067 11.00000 0.05203 0.06077 =
0.07416 -0.03291 -0.01653 -0.00634
N1 4 -0.198239 0.889875 0.065918 11.00000 0.04540 0.05724 =
0.05905 -0.02767 -0.00704 -0.00923
H1N 2 -0.284821 0.867944 0.037891 11.00000 -1.20000
N2 4 0.171847 0.563582 0.070845 11.00000 0.05003 0.05293 =
0.06036 -0.02575 -0.01225 -0.00697
H2N 2 0.179223 0.490409 0.049868 11.00000 -1.20000
N3 4 0.325666 0.566077 0.133261 11.00000 0.04726 0.05242 =
0.04955 -0.01606 -0.00768 -0.01147
C1 1 -0.415439 0.967368 0.224692 11.00000 0.04376 0.04870 =
0.05656 -0.02145 -0.00116 -0.00783
C2 1 -0.328576 0.943569 0.318857 11.00000 0.05520 0.10348 =
0.06057 -0.03024 -0.00053 -0.02257
AFIX 43
H2 2 -0.199533 0.958848 0.324412 11.00000 -1.20000
AFIX 0
C3 1 -0.432952 0.897072 0.404930 11.00000 0.07558 0.11910 =
0.05410 -0.02123 -0.00188 -0.01896
AFIX 43
H3 2 -0.374571 0.880441 0.468907 11.00000 -1.20000
AFIX 0
C4 1 -0.623114 0.875363 0.396080 11.00000 0.07196 0.08976 =
0.06558 -0.01565 0.01962 -0.02300
C5 1 -0.708983 0.898993 0.302599 11.00000 0.06116 0.13931 =
0.07956 -0.02340 0.00821 -0.04424
AFIX 43
H5 2 -0.837854 0.883342 0.297257 11.00000 -1.20000
AFIX 0
C6 1 -0.606597 0.945650 0.216487 11.00000 0.05771 0.11815 =
0.06171 -0.01990 -0.00151 -0.03488
AFIX 43
H6 2 -0.666116 0.962570 0.152735 11.00000 -1.20000
AFIX 0
C7 1 -0.014905 0.782071 0.105255 11.00000 0.04554 0.05161 =
0.04752 -0.01687 -0.00299 -0.01290
AFIX 23
H7A 2 -0.022691 0.748572 0.178490 11.00000 -1.20000
H7B 2 0.105960 0.818535 0.089975 11.00000 -1.20000
AFIX 0
C8 1 -0.001579 0.665877 0.055553 11.00000 0.04616 0.05107 =
0.04547 -0.01450 -0.00292 -0.01417
C9 1 0.482483 0.463250 0.145039 11.00000 0.05333 0.05267 =
0.05483 -0.02004 -0.00413 -0.01390
AFIX 43
H9 2 0.486624 0.393537 0.112435 11.00000 -1.20000
AFIX 0
C10 1 0.656767 0.453547 0.209506 11.00000 0.04688 0.04830 =
0.04826 -0.01097 -0.00320 -0.01153
C11 1 0.649041 0.547866 0.267510 11.00000 0.05805 0.05829 =
0.06471 -0.02000 -0.00998 -0.00685
AFIX 43
H11 2 0.530130 0.618121 0.266545 11.00000 -1.20000
AFIX 0
C12 1 0.815231 0.538541 0.326348 11.00000 0.07518 0.07689 =
0.06059 -0.02438 -0.01069 -0.02383
AFIX 43
H12 2 0.808568 0.601525 0.365387 11.00000 -1.20000
AFIX 0
C13 1 0.990645 0.435433 0.326787 11.00000 0.05570 0.08915 =
0.04807 -0.00563 -0.00765 -0.02610
C14 1 1.001786 0.340649 0.271857 11.00000 0.04991 0.07465 =
0.06884 -0.00552 -0.00391 -0.00252
AFIX 43
H14 2 1.120998 0.270324 0.273761 11.00000 -1.20000
AFIX 0
C15 1 0.833419 0.349704 0.212776 11.00000 0.05838 0.05570 =
0.06436 -0.01831 -0.00188 -0.01005
AFIX 43
H15 2 0.840415 0.284985 0.175185 11.00000 -1.20000
AFIX 0
HKLF 4
REM GSH10 P-1
REM wR2 = 0.119801, GooF = S = 1.03547, Restrained GooF = 1.03581 for all data
REM R1 = 0.048020 for 2600 Fo > 4sig(Fo) and 0.073106 for all 3598 data
REM 223 parameters refined using 2 restraints
END
WGHT 0.0407 0.5495
REM Instructions for potential hydrogen bonds
HTAB N1 O2_$1
HTAB N2 O3_$2
REM Highest difference peak 0.333, deepest hole -0.298, 1-sigma level 0.044
Q1 1 1.2349 0.3541 0.3610 11.00000 0.05 0.33
Q2 1 -0.6970 0.8165 0.5625 11.00000 0.05 0.23
Q3 1 -0.7912 0.9057 0.4756 11.00000 0.05 0.18
Q4 1 -0.2247 1.0451 0.1607 11.00000 0.05 0.18
Q5 1 -0.3754 0.9901 0.1619 11.00000 0.05 0.18
Q6 1 -0.7407 0.9891 0.3231 11.00000 0.05 0.17
Q7 1 -0.1070 0.5771 -0.0165 11.00000 0.05 0.17
Q8 1 -0.2196 0.9408 0.0903 11.00000 0.05 0.16
Q9 1 1.1251 0.3703 0.4479 11.00000 0.05 0.16
Q10 1 -0.1239 1.0489 0.1000 11.00000 0.05 0.15
Q11 1 -0.5276 1.1333 0.0602 11.00000 0.05 0.15
Q12 1 -0.3313 0.9681 0.1756 11.00000 0.05 0.15
Q13 1 0.7673 0.5733 0.2587 11.00000 0.05 0.15
Q14 1 0.4992 0.6803 0.2322 11.00000 0.05 0.15
Q15 1 0.5976 0.4735 0.1595 11.00000 0.05 0.15
Q16 1 -0.0761 0.9867 0.1206 11.00000 0.05 0.15
Q17 1 0.5768 0.4620 0.1817 11.00000 0.05 0.14
Q18 1 0.0070 1.0756 0.1016 11.00000 0.05 0.14
Q19 1 -0.2038 0.7544 -0.0164 11.00000 0.05 0.14
Q20 1 -0.0604 0.9858 0.2044 11.00000 0.05 0.14
Q21 1 -0.1789 0.8246 0.1154 11.00000 0.05 0.14
Q22 1 -0.3438 0.9214 0.2617 11.00000 0.05 0.14
Q23 1 0.8889 0.3158 0.2701 11.00000 0.05 0.13
Q24 1 -0.2371 0.8854 0.0111 11.00000 0.05 0.13
Q25 1 -0.4411 1.1580 0.0132 11.00000 0.05 0.13
Q26 1 0.9956 0.4076 0.2822 11.00000 0.05 0.13
Q27 1 1.1664 0.4831 0.3787 11.00000 0.05 0.13
Q28 1 -0.6995 0.7329 0.4770 11.00000 0.05 0.13
Q29 1 -0.1976 0.7837 0.2810 11.00000 0.05 0.13
Q30 1 1.3567 0.5002 0.3837 11.00000 0.05 0.13
;
_shelx_res_checksum 25286
_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
Cl Cl1 -0.75370(19) 0.81534(16) 0.50474(9) 0.1284(5) Uani d 1 . .
Cl Cl2 1.20248(15) 0.42711(14) 0.39838(7) 0.1119(4) Uani d 1 . .
S S1 -0.27969(10) 1.01993(7) 0.11321(5) 0.04891(19) Uani d 1 . .
O O1 -0.1031(3) 1.05461(19) 0.14290(15) 0.0609(5) Uani d 1 . .
O O2 -0.4241(3) 1.12132(19) 0.04119(15) 0.0628(5) Uani d 1 . .
O O3 -0.1441(3) 0.66440(19) 0.00307(15) 0.0601(5) Uani d 1 . .
N N1 -0.1982(3) 0.8899(2) 0.06592(17) 0.0518(5) Uani d 1 . .
H H1N -0.285(4) 0.868(3) 0.038(2) 0.062 Uiso d 1 . .
N N2 0.1718(3) 0.5636(2) 0.07085(17) 0.0529(5) Uani d 1 . .
H H2N 0.179(4) 0.490(2) 0.050(2) 0.063 Uiso d 1 . .
N N3 0.3257(3) 0.5661(2) 0.13326(15) 0.0490(5) Uani d 1 . .
C C1 -0.4154(4) 0.9674(3) 0.2247(2) 0.0487(6) Uani d 1 . .
C C2 -0.3286(5) 0.9436(4) 0.3189(2) 0.0707(8) Uani d 1 . .
H H2 -0.199533 0.958848 0.324412 0.085 Uiso calc 1 . .
C C3 -0.4330(5) 0.8971(4) 0.4049(2) 0.0840(10) Uani d 1 . .
H H3 -0.374571 0.880441 0.468907 0.101 Uiso calc 1 . .
C C4 -0.6231(5) 0.8754(4) 0.3961(3) 0.0767(9) Uani d 1 . .
C C5 -0.7090(5) 0.8990(4) 0.3026(3) 0.0909(11) Uani d 1 . .
H H5 -0.837854 0.883342 0.297257 0.109 Uiso calc 1 . .
C C6 -0.6066(5) 0.9456(4) 0.2165(2) 0.0773(9) Uani d 1 . .
H H6 -0.666116 0.962570 0.152735 0.093 Uiso calc 1 . .
C C7 -0.0149(4) 0.7821(3) 0.10526(19) 0.0471(6) Uani d 1 . .
H H7A -0.022691 0.748572 0.178490 0.057 Uiso calc 1 . .
H H7B 0.105960 0.818535 0.089975 0.057 Uiso calc 1 . .
C C8 -0.0016(4) 0.6659(3) 0.05555(18) 0.0466(6) Uani d 1 . .
C C9 0.4825(4) 0.4633(3) 0.1450(2) 0.0521(6) Uani d 1 . .
H H9 0.486624 0.393537 0.112435 0.063 Uiso calc 1 . .
C C10 0.6568(4) 0.4535(3) 0.20951(19) 0.0480(6) Uani d 1 . .
C C11 0.6490(4) 0.5479(3) 0.2675(2) 0.0606(7) Uani d 1 . .
H H11 0.530130 0.618121 0.266545 0.073 Uiso calc 1 . .
C C12 0.8152(5) 0.5385(3) 0.3263(2) 0.0682(8) Uani d 1 . .
H H12 0.808568 0.601525 0.365387 0.082 Uiso calc 1 . .
C C13 0.9906(4) 0.4354(4) 0.3268(2) 0.0648(8) Uani d 1 . .
C C14 1.0018(4) 0.3406(3) 0.2719(2) 0.0692(8) Uani d 1 . .
H H14 1.120998 0.270324 0.273761 0.083 Uiso calc 1 . .
C C15 0.8334(4) 0.3497(3) 0.2128(2) 0.0596(7) Uani d 1 . .
H H15 0.840415 0.284985 0.175185 0.071 Uiso calc 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 0.1225(9) 0.1721(12) 0.0862(7) -0.0563(9) 0.0375(7) -0.0130(8)
Cl2 0.0737(6) 0.1848(12) 0.0779(6) -0.0439(7) -0.0247(5) -0.0185(7)
S1 0.0460(3) 0.0478(4) 0.0565(4) -0.0123(3) -0.0034(3) -0.0181(3)
O1 0.0516(10) 0.0629(12) 0.0799(13) -0.0225(9) -0.0016(9) -0.0303(10)
O2 0.0616(12) 0.0518(11) 0.0695(13) -0.0097(9) -0.0111(9) -0.0076(9)
O3 0.0520(10) 0.0608(11) 0.0742(13) -0.0063(9) -0.0165(9) -0.0329(10)
N1 0.0454(12) 0.0572(13) 0.0591(14) -0.0092(10) -0.0070(10) -0.0277(11)
N2 0.0500(12) 0.0529(13) 0.0604(14) -0.0070(10) -0.0122(10) -0.0258(11)
N3 0.0473(12) 0.0524(13) 0.0495(12) -0.0115(10) -0.0077(9) -0.0161(10)
C1 0.0438(13) 0.0487(14) 0.0566(15) -0.0078(11) -0.0012(11) -0.0215(12)
C2 0.0552(17) 0.103(3) 0.0606(18) -0.0226(16) -0.0005(14) -0.0302(18)
C3 0.076(2) 0.119(3) 0.0541(19) -0.019(2) -0.0019(16) -0.0212(19)
C4 0.072(2) 0.090(2) 0.066(2) -0.0230(18) 0.0196(16) -0.0157(18)
C5 0.061(2) 0.139(3) 0.080(2) -0.044(2) 0.0082(17) -0.023(2)
C6 0.0577(18) 0.118(3) 0.0617(19) -0.0349(18) -0.0015(15) -0.0199(19)
C7 0.0455(13) 0.0516(14) 0.0475(14) -0.0129(11) -0.0030(11) -0.0169(12)
C8 0.0462(13) 0.0511(14) 0.0455(14) -0.0142(11) -0.0029(11) -0.0145(11)
C9 0.0533(15) 0.0527(15) 0.0548(15) -0.0139(12) -0.0041(12) -0.0200(12)
C10 0.0469(13) 0.0483(14) 0.0483(14) -0.0115(11) -0.0032(11) -0.0110(11)
C11 0.0581(16) 0.0583(17) 0.0647(18) -0.0068(13) -0.0100(13) -0.0200(14)
C12 0.075(2) 0.077(2) 0.0606(18) -0.0238(17) -0.0107(15) -0.0244(16)
C13 0.0557(17) 0.089(2) 0.0481(16) -0.0261(16) -0.0076(13) -0.0056(15)
C14 0.0499(16) 0.075(2) 0.0688(19) -0.0025(14) -0.0039(14) -0.0055(16)
C15 0.0584(16) 0.0557(16) 0.0644(18) -0.0101(13) -0.0019(13) -0.0183(14)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O1 S1 O2 . . 119.70(12) ?
O1 S1 N1 . . 107.02(11) ?
O2 S1 N1 . . 106.60(12) ?
O1 S1 C1 . . 107.38(12) ?
O2 S1 C1 . . 107.41(12) ?
N1 S1 C1 . . 108.32(12) ?
C7 N1 S1 . . 121.73(16) ?
C7 N1 H1N . . 117(2) ?
S1 N1 H1N . . 116(2) ?
C8 N2 N3 . . 119.7(2) ?
C8 N2 H2N . . 119.9(19) ?
N3 N2 H2N . . 119.6(19) ?
C9 N3 N2 . . 115.3(2) ?
C2 C1 C6 . . 120.1(3) ?
C2 C1 S1 . . 120.5(2) ?
C6 C1 S1 . . 119.3(2) ?
C1 C2 C3 . . 119.8(3) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 119.7(3) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C5 C4 C3 . . 120.4(3) ?
C5 C4 Cl1 . . 119.9(3) ?
C3 C4 Cl1 . . 119.7(3) ?
C4 C5 C6 . . 120.3(3) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.7(3) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
N1 C7 C8 . . 107.76(19) ?
N1 C7 H7A . . 110.2 ?
C8 C7 H7A . . 110.2 ?
N1 C7 H7B . . 110.2 ?
C8 C7 H7B . . 110.2 ?
H7A C7 H7B . . 108.5 ?
O3 C8 N2 . . 121.3(2) ?
O3 C8 C7 . . 121.3(2) ?
N2 C8 C7 . . 117.4(2) ?
N3 C9 C10 . . 120.7(2) ?
N3 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C15 C10 C11 . . 118.6(2) ?
C15 C10 C9 . . 119.8(2) ?
C11 C10 C9 . . 121.6(2) ?
C12 C11 C10 . . 120.8(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
C13 C12 C11 . . 119.3(3) ?
C13 C12 H12 . . 120.3 ?
C11 C12 H12 . . 120.3 ?
C14 C13 C12 . . 121.2(3) ?
C14 C13 Cl2 . . 119.7(3) ?
C12 C13 Cl2 . . 119.1(2) ?
C13 C14 C15 . . 119.5(3) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C10 C15 C14 . . 120.6(3) ?
C10 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
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
Cl1 C4 . 1.735(3) ?
Cl2 C13 . 1.738(3) ?
S1 O1 . 1.4275(18) ?
S1 O2 . 1.4297(19) ?
S1 N1 . 1.594(2) ?
S1 C1 . 1.764(3) ?
O3 C8 . 1.229(3) ?
N1 C7 . 1.450(3) ?
N1 H1N . 0.818(17) ?
N2 C8 . 1.341(3) ?
N2 N3 . 1.380(3) ?
N2 H2N . 0.861(17) ?
N3 C9 . 1.273(3) ?
C1 C2 . 1.373(4) ?
C1 C6 . 1.374(4) ?
C2 C3 . 1.375(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.369(5) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.362(5) ?
C5 C6 . 1.368(4) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.500(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C9 C10 . 1.467(3) ?
C9 H9 . 0.9300 ?
C10 C15 . 1.375(4) ?
C10 C11 . 1.390(4) ?
C11 C12 . 1.377(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.371(4) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.360(4) ?
C14 C15 . 1.392(4) ?
C14 H14 . 0.9300 ?
C15 H15 . 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 H1N O2 2_475 0.818(17) 2.246(19) 3.032(3) 162(3) yes
N1 H1N O3 1_555 0.815(17) 2.23(3) 2.609(3) 109(2) y
N2 H2N O3 2_565 0.861(17) 1.977(18) 2.829(3) 170(3) yes
C15 H15 O1 1_645 0.93 2.45 3.330(3) 157 y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 S1 N1 C7 . . . . 35.4(2) ?
O2 S1 N1 C7 . . . . 164.6(2) ?
C1 S1 N1 C7 . . . . -80.1(2) ?
C8 N2 N3 C9 . . . . 178.5(2) ?
O1 S1 C1 C2 . . . . -10.8(3) ?
O2 S1 C1 C2 . . . . -140.8(2) ?
N1 S1 C1 C2 . . . . 104.5(2) ?
O1 S1 C1 C6 . . . . 171.5(2) ?
O2 S1 C1 C6 . . . . 41.5(3) ?
N1 S1 C1 C6 . . . . -73.3(3) ?
C6 C1 C2 C3 . . . . 0.4(5) ?
S1 C1 C2 C3 . . . . -177.3(3) ?
C1 C2 C3 C4 . . . . -0.2(5) ?
C2 C3 C4 C5 . . . . 0.3(6) ?
C2 C3 C4 Cl1 . . . . 179.5(3) ?
C3 C4 C5 C6 . . . . -0.5(6) ?
Cl1 C4 C5 C6 . . . . -179.7(3) ?
C4 C5 C6 C1 . . . . 0.6(6) ?
C2 C1 C6 C5 . . . . -0.6(5) ?
S1 C1 C6 C5 . . . . 177.1(3) ?
S1 N1 C7 C8 . . . . 171.09(18) ?
N3 N2 C8 O3 . . . . -177.6(2) ?
N3 N2 C8 C7 . . . . 2.2(4) ?
N1 C7 C8 O3 . . . . -9.0(3) ?
N1 C7 C8 N2 . . . . 171.1(2) ?
N2 N3 C9 C10 . . . . 180.0(2) ?
N3 C9 C10 C15 . . . . -173.1(3) ?
N3 C9 C10 C11 . . . . 6.4(4) ?
C15 C10 C11 C12 . . . . 0.6(4) ?
C9 C10 C11 C12 . . . . -179.0(3) ?
C10 C11 C12 C13 . . . . 0.5(5) ?
C11 C12 C13 C14 . . . . -1.4(5) ?
C11 C12 C13 Cl2 . . . . 178.2(2) ?
C12 C13 C14 C15 . . . . 1.1(5) ?
Cl2 C13 C14 C15 . . . . -178.5(2) ?
C11 C10 C15 C14 . . . . -0.9(4) ?
C9 C10 C15 C14 . . . . 178.7(3) ?
C13 C14 C15 C10 . . . . 0.1(5) ?
_cod_database_fobs_code 2243865