#------------------------------------------------------------------------------
#$Date: 2026-09-03 22:12:44 +0100 (Thu, 03 Sep 2026) $
#$Revision: 306851 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/35/2023550.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_2023550
loop_
_publ_author_name
'Kumar, Sharatha'
'H\"okelek, Tuncer'
_publ_section_title
;
Synthesis, crystal structure determination, Hirshfeld surface and crystal
void analyses, interaction energy calculations and energy frameworks of
N-(2-methylphenyl)-N′-pivaloylthiourea
;
_journal_coeditor_code WM5810
_journal_issue 10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi 10.1107/S205698902600890X
_journal_volume 82
_journal_year 2026
_chemical_formula_iupac 'C13 H18 N2 O S'
_chemical_formula_moiety 'C13 H18 N2 O S'
_chemical_formula_sum 'C13 H18 N2 O S'
_chemical_formula_weight 250.35
_chemical_name_common
;
N-(2-Methylphenyl)-N'-pivaloylthiourea
;
_chemical_name_systematic
;
3-(2,2-Dimethylpropanoyl)-1-(2-methylphenyl)thiourea
;
_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 SHELXL-2018/3
_cell_angle_alpha 63.290(4)
_cell_angle_beta 81.600(3)
_cell_angle_gamma 84.340(4)
_cell_formula_units_Z 2
_cell_length_a 6.1050(4)
_cell_length_b 10.7020(3)
_cell_length_c 11.8910(3)
_cell_measurement_reflns_used 2155
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 27.71
_cell_measurement_theta_min 3.36
_cell_volume 686.08(6)
_computing_cell_refinement
;
CrysAlisRED (Oxford Diffraction, 2009)
;
_computing_data_collection
;
CrysAlisCCD (Oxford Diffraction, 2009)
;
_computing_data_reduction
;
CrysAlisRED (Oxford Diffraction, 2009)
;
_computing_molecular_graphics
;
Ortep-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur
with Sapphire CCD Detector
;
_diffrn_measurement_method
;
Rotation method data acquisition using omega scans.
;
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0103
_diffrn_reflns_av_unetI/netI 0.0152
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 14
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_number 4335
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.371
_diffrn_reflns_theta_min 3.376
_exptl_absorpt_coefficient_mu 0.223
_exptl_absorpt_correction_T_max 0.9652
_exptl_absorpt_correction_T_min 0.8967
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis RED; Oxford Diffraction, 2009)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.212
_exptl_crystal_description prism
_exptl_crystal_F_000 268
_exptl_crystal_size_max 0.500
_exptl_crystal_size_mid 0.480
_exptl_crystal_size_min 0.160
_refine_diff_density_max 0.713
_refine_diff_density_min -0.239
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.155
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 160
_refine_ls_number_reflns 2756
_refine_ls_number_restraints 3
_refine_ls_restrained_S_all 1.156
_refine_ls_R_factor_all 0.0781
_refine_ls_R_factor_gt 0.0641
_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^)+(0.0561P)^2^+0.6536P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1526
_refine_ls_wR_factor_ref 0.1639
_reflns_number_gt 2287
_reflns_number_total 2756
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file wm5810.cif
_cod_data_source_block I
_cod_database_code 2023550
_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 0.897
_shelx_estimated_absorpt_t_max 0.965
_shelx_hkl_file
;
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0 0 2 27065.5 98.8429 4
0 0 3 32015.6 125.411 0
0 0 3 32558.7 133.647 4
0 0 3 31913.7 121.159 5
0 0 4 19841.1 122.914 4
0 0 4 19591.4 115.630 0
0 0 5 46065.0 199.462 0
0 0 5 47449.4 213.273 4
0 0 6 87.2931 38.6731 4
0 0 7 869.862 54.0044 4
0 0 8 1595.78 71.2642 4
0 0 9 1395.77 76.2131 4
0 0 10 512.914 65.7899 4
0 0 11 3056.25 103.982 4
0 0 12 31.7530 64.2606 4
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0 -1 5 67107.9 225.246 2
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0 -1 5 66103.0 266.214 4
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0 -1 4 22693.7 76.3593 6
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0 -1 3 2082.25 44.7316 4
0 -1 2 119345. 191.872 5
0 -1 2 115887. 825.644 1
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6 7 3 95.5221 54.8357 6
6 7 4 19.7422 51.9085 6
6 7 5-46.5286 44.8796 6
6 7 6-36.7874 44.8562 6
6 7 7 129.097 57.9917 6
6 7 8-14.1628 55.1638 6
6 7 9-78.3736 58.8406 6
6 7 10 23.7641 48.1373 6
6 7 11 192.044 58.6307 6
-6 -8 0 720.175 69.7414 2
-6 -8 -1 162.943 57.4697 2
6 8 1 701.639 73.5450 6
6 8 2 87.1910 56.2216 6
-6 -8 -2 207.871 54.3232 2
6 8 3-113.833 58.9964 6
-6 -8 -3 77.7425 49.1497 2
6 8 4-15.5665 52.2691 6
6 8 5 211.000 64.5823 6
6 8 6 128.922 69.6556 6
6 8 7 546.036 71.3531 6
6 8 8 210.869 70.6972 6
6 8 9 172.360 70.0151 6
6 8 10 233.659 71.3579 6
6 9 2-109.713 70.7136 6
-6 -9 -2 178.790 58.5741 2
6 9 3 237.784 73.8421 6
-6 -9 -3 140.808 49.6200 2
6 9 4 234.503 73.3502 6
6 9 5-35.0377 55.3620 6
6 9 6-71.5412 68.4520 6
6 9 7-92.1477 59.1520 6
7 -5 -3 402.818 45.4296 6
-7 4 4 234.949 83.1599 5
7 -4 -3-88.7225 39.3478 6
7 -4 -2 1124.41 55.5045 6
-7 4 2 1163.78 82.1124 5
7 -4 -1 1755.00 71.3214 6
7 -4 0 1437.48 70.2390 6
-7 3 4 1195.14 98.6806 5
-7 3 3 685.138 83.3785 5
-7 3 2 125.548 65.2667 5
7 -3 -1 160.859 32.6480 6
-7 3 1 175.692 72.3072 5
7 -3 0-12.6936 39.0680 6
7 -3 1 374.662 45.4310 6
7 -3 2-44.8466 39.7993 6
-7 2 4 10.2677 71.4932 5
-7 2 3 891.218 80.8285 5
7 -2 -2 1800.19 62.3239 6
-7 2 2 1606.85 98.9039 5
7 -2 -1 759.497 50.5678 6
7 -2 0 147.483 41.7516 6
7 -2 1 196.361 45.4503 6
7 -2 2-6.02579 43.9559 6
7 -2 3 374.102 54.2929 6
7 -2 4 357.400 50.8523 6
-7 1 3-71.1684 66.4324 5
-7 1 2 58.8370 73.3134 5
7 -1 -1-81.8456 34.4786 6
7 -1 0 48.7850 33.0356 6
7 -1 1 581.135 50.7026 6
7 -1 2 1951.97 74.3871 6
7 -1 3 390.328 53.2499 6
7 -1 4 160.203 52.9471 6
7 -1 5 284.213 48.5508 6
-7 0 3 1159.46 89.2591 5
-7 0 2 255.885 81.3647 5
7 0 -1 352.592 29.6444 6
7 0 0 31.7862 37.3635 6
7 0 1-44.6099 33.2986 6
7 0 2-49.1512 38.0424 6
7 0 3-10.6920 45.3510 6
7 0 4-104.771 45.6929 6
7 0 5 396.742 51.3937 6
7 0 6 780.822 57.8763 6
-7 -1 3-111.956 61.1133 5
-7 -1 2 1011.34 89.5516 5
7 1 -1 345.067 40.3073 6
-7 -1 1 183.480 73.8537 5
7 1 0 131.719 35.4580 6
7 1 1 525.330 47.3177 6
7 1 2 557.143 49.3201 6
7 1 3 296.844 50.9905 6
7 1 4 93.1790 40.0334 6
7 1 5 155.254 44.2170 6
7 1 6 335.825 58.7649 6
7 1 7 260.345 47.8847 6
-7 -2 2 399.010 79.2290 5
-7 -2 1-72.8496 74.0418 5
7 2 0 38.7153 54.5866 6
7 2 2-32.6927 46.2327 6
7 2 3 148.404 46.0257 6
7 2 4 435.063 48.0965 6
7 2 5-67.9960 46.9955 6
7 2 6 264.740 49.7426 6
7 2 7 733.914 59.7376 6
7 2 8 409.370 46.8775 6
-7 -3 2 34.3733 61.0586 5
-7 -3 1 140.758 59.2781 5
7 3 0 771.330 62.6505 6
7 3 2 183.736 48.0040 6
7 3 3-7.19769 52.4921 6
7 3 4 126.879 49.6608 6
7 3 5 32.1203 57.1468 6
7 3 6-35.4442 56.3378 6
7 3 7 194.082 61.2892 6
7 3 8 63.2736 53.6453 6
-7 -4 1 1231.38 86.2269 5
7 4 0 349.387 55.3243 6
7 4 1 537.210 62.9573 6
7 4 2 1775.94 79.5054 6
7 4 3 1158.28 69.1287 6
7 4 4 218.561 55.6510 6
7 4 5 44.0189 59.4742 6
7 4 7-112.418 53.8072 6
7 4 8 6.52237 61.0987 6
-7 -5 0 96.0240 56.0540 5
7 5 1 654.016 65.6173 6
7 5 2 1007.90 72.9815 6
7 5 3 247.172 58.3996 6
7 5 4 159.439 60.4371 6
7 5 5 32.8676 58.6667 6
7 5 6 97.1099 49.7161 6
7 5 7 85.8507 50.5641 6
-7 -6 0 441.643 83.9235 5
7 6 1 58.8888 59.4312 6
7 6 2 205.451 50.0282 6
7 6 3 610.488 67.8441 6
7 6 4 285.684 56.3920 6
7 6 5 199.708 57.8825 6
7 6 6 383.788 62.6271 6
7 7 2 584.012 69.9798 6
;
_shelx_hkl_checksum 50055
_shelx_res_file
;
TITL SPVT2 IN P-1
shelx.res
created by SHELXL-2018/3 at 12:15:34 on 24-Jul-2026
CELL 0.71073 6.1050 10.7020 11.8910 63.290 81.600 84.340
ZERR 2.00 0.0004 0.0003 0.0003 0.004 0.003 0.004
LATT 1
SFAC C H N O S
UNIT 26 36 4 2 2
MERG 2
OMIT -1 -2 1
OMIT 1 1 0
OMIT -4 0 10
SHEL 12 0.8
DELU 0.001 0.001 C5 C6
DFIX 0.86 0.02 N1 H1N N2 H2N
HTAB N1 O1
HTAB N1 O1
EQIV $1 -x+1, -y+1, -z+1
HTAB N2 S1_$1
FMAP 2
PLAN 30
SIZE 0.160 0.480 0.500
ACTA
BOND $H
CONF
LIST 4
L.S. 14
WGHT 0.056100 0.653600
FVAR 7.67414
C1 1 0.653453 0.004130 0.757148 11.00000 0.06564 0.03767 =
0.04732 -0.01290 0.01105 0.01031
C2 1 0.472929 -0.070842 0.778854 11.00000 0.06569 0.04699 =
0.05556 -0.02168 0.00144 0.00942
C3 1 0.409572 -0.170185 0.907377 11.00000 0.08401 0.04918 =
0.05748 -0.01658 0.00963 0.01413
AFIX 43
H3 2 0.285478 -0.223253 0.927043 11.00000 -1.20000
AFIX 0
C4 1 0.531039 -0.186154 0.999499 11.00000 0.09397 0.06217 =
0.05532 -0.01823 0.00659 0.01553
AFIX 43
H4 2 0.486587 -0.250364 1.082242 11.00000 -1.20000
AFIX 0
C5 1 0.714967 -0.112986 0.977166 11.00000 0.10840 0.07443 =
0.04847 -0.01741 -0.01775 0.02149
AFIX 43
H5 2 0.795826 -0.128953 1.043172 11.00000 -1.20000
AFIX 0
C6 1 0.781143 -0.014121 0.854859 11.00000 0.09350 0.06116 =
0.04818 -0.01861 -0.01493 0.02750
AFIX 43
H6 2 0.904989 0.038526 0.837313 11.00000 -1.20000
AFIX 0
C7 1 0.645514 0.236682 0.577806 11.00000 0.04456 0.03526 =
0.03399 -0.01061 -0.00003 0.00045
C8 1 0.941564 0.300141 0.394352 11.00000 0.03684 0.04310 =
0.03851 -0.01606 -0.00101 -0.00044
C9 1 1.028449 0.425401 0.273717 11.00000 0.04295 0.03959 =
0.04135 -0.01391 0.00649 -0.00109
C10 1 0.844125 0.491159 0.186765 11.00000 0.07227 0.06413 =
0.03980 -0.01385 -0.00424 0.00380
AFIX 33
H10A 2 0.722387 0.522879 0.229562 11.00000 -1.50000
H10B 2 0.900447 0.569074 0.110502 11.00000 -1.50000
H10C 2 0.794361 0.422614 0.165898 11.00000 -1.50000
AFIX 0
C11 1 1.106888 0.531513 0.311030 11.00000 0.05921 0.06144 =
0.07604 -0.03171 0.00852 -0.01759
AFIX 33
H11A 2 0.984175 0.562679 0.353691 11.00000 -1.50000
H11B 2 1.219945 0.488307 0.366534 11.00000 -1.50000
H11C 2 1.165792 0.610173 0.236291 11.00000 -1.50000
AFIX 0
C12 1 1.221365 0.375124 0.205993 11.00000 0.06887 0.06068 =
0.06601 -0.01802 0.02959 0.00264
AFIX 33
H12A 2 1.277779 0.453031 0.129752 11.00000 -1.50000
H12B 2 1.336465 0.334007 0.260380 11.00000 -1.50000
H12C 2 1.171636 0.306594 0.185095 11.00000 -1.50000
AFIX 0
C13 1 0.352591 -0.055042 0.678390 11.00000 0.08176 0.06477 =
0.07355 -0.02396 -0.00393 -0.00514
AFIX 33
H13A 2 0.230783 -0.116751 0.712468 11.00000 -1.50000
H13B 2 0.297175 0.039974 0.636992 11.00000 -1.50000
H13C 2 0.449045 -0.077743 0.618279 11.00000 -1.50000
AFIX 0
N1 3 0.728652 0.106180 0.630183 11.00000 0.05269 0.04039 =
0.04071 -0.00877 0.00920 0.00719
N2 3 0.754974 0.327325 0.462090 11.00000 0.04417 0.03545 =
0.03938 -0.00881 0.00583 0.00327
O1 4 1.029248 0.183509 0.429590 11.00000 0.05371 0.04378 =
0.05467 -0.01229 0.00795 0.00944
S1 5 0.422039 0.295577 0.640544 11.00000 0.05729 0.03948 =
0.04821 -0.01245 0.01439 0.00483
H1N 2 0.841209 0.083968 0.592333 11.00000 -1.20000
H2N 2 0.702709 0.411258 0.434276 11.00000 -1.20000
HKLF 4
REM SPVT2 IN P-1
REM wR2 = 0.1639, GooF = S = 1.155, Restrained GooF = 1.156 for all data
REM R1 = 0.0641 for 2287 Fo > 4sig(Fo) and 0.0781 for all 2756 data
REM 160 parameters refined using 3 restraints
END
WGHT 0.0561 0.6536
REM Highest difference peak 0.713, deepest hole -0.239, 1-sigma level 0.056
Q1 1 0.2848 -0.1569 0.8205 11.00000 0.05 0.71
Q2 1 0.6329 -0.0460 0.8409 11.00000 0.05 0.63
Q3 1 0.5503 0.0057 0.7084 11.00000 0.05 0.34
Q4 1 0.5580 -0.1266 0.9304 11.00000 0.05 0.32
Q5 1 0.8089 -0.0432 0.8569 11.00000 0.05 0.24
Q6 1 0.7869 -0.0228 0.8963 11.00000 0.05 0.21
Q7 1 1.0193 0.5814 0.3632 11.00000 0.05 0.19
Q8 1 0.9682 0.3670 0.3245 11.00000 0.05 0.19
Q9 1 0.4125 0.0275 0.5806 11.00000 0.05 0.18
Q10 1 1.3376 0.4579 0.1593 11.00000 0.05 0.18
Q11 1 1.3326 0.3630 0.2665 11.00000 0.05 0.18
Q12 1 1.3655 0.3159 0.3161 11.00000 0.05 0.16
Q13 1 0.3985 -0.1486 0.6303 11.00000 0.05 0.16
Q14 1 0.6916 0.0377 0.7407 11.00000 0.05 0.16
Q15 1 0.8397 0.1700 0.8153 11.00000 0.05 0.15
Q16 1 0.3500 -0.1998 0.9642 11.00000 0.05 0.15
Q17 1 0.3946 0.3422 0.5493 11.00000 0.05 0.15
Q18 1 1.1184 0.3844 0.2580 11.00000 0.05 0.15
Q19 1 0.5629 0.2999 0.6613 11.00000 0.05 0.15
Q20 1 0.6957 0.2747 0.5136 11.00000 0.05 0.14
Q21 1 0.5358 0.2816 0.5823 11.00000 0.05 0.14
Q22 1 0.6290 -0.0001 1.0842 11.00000 0.05 0.14
Q23 1 1.1013 0.4840 0.4427 11.00000 0.05 0.14
Q24 1 1.3033 0.2875 0.2457 11.00000 0.05 0.14
Q25 1 1.3378 0.2980 0.4619 11.00000 0.05 0.13
Q26 1 0.5664 -0.2018 0.6339 11.00000 0.05 0.13
Q27 1 0.2169 0.3097 0.6086 11.00000 0.05 0.13
Q28 1 0.5409 -0.1815 0.5615 11.00000 0.05 0.13
Q29 1 0.9508 0.4583 0.2402 11.00000 0.05 0.13
Q30 1 1.2255 0.3149 0.4384 11.00000 0.05 0.13
;
_shelx_res_checksum 33612
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 0.6535(6) 0.0041(3) 0.7571(3) 0.0553(8) Uani d 1 . .
C C2 0.4729(6) -0.0708(3) 0.7789(3) 0.0582(8) Uani d 1 . .
C C3 0.4096(7) -0.1702(4) 0.9074(3) 0.0694(10) Uani d 1 . .
H H3 0.285478 -0.223253 0.927043 0.083 Uiso calc 1 . .
C C4 0.5310(8) -0.1862(4) 0.9995(4) 0.0765(11) Uani d 1 . .
H H4 0.486587 -0.250364 1.082242 0.092 Uiso calc 1 . .
C C5 0.7150(8) -0.1130(4) 0.9772(3) 0.0817(12) Uani d 1 . .
H H5 0.795826 -0.128953 1.043172 0.098 Uiso calc 1 . .
C C6 0.7811(7) -0.0141(4) 0.8549(3) 0.0712(10) Uani d 1 . .
H H6 0.904989 0.038526 0.837313 0.085 Uiso calc 1 . .
C C7 0.6455(4) 0.2367(3) 0.5778(2) 0.0404(6) Uani d 1 . .
C C8 0.9416(4) 0.3001(3) 0.3944(2) 0.0407(6) Uani d 1 . .
C C9 1.0284(5) 0.4254(3) 0.2737(3) 0.0441(6) Uani d 1 . .
C C10 0.8441(6) 0.4912(4) 0.1868(3) 0.0629(9) Uani d 1 . .
H H10A 0.722387 0.522879 0.229562 0.094 Uiso calc 1 . .
H H10B 0.900447 0.569074 0.110502 0.094 Uiso calc 1 . .
H H10C 0.794361 0.422614 0.165898 0.094 Uiso calc 1 . .
C C11 1.1069(6) 0.5315(4) 0.3110(4) 0.0657(9) Uani d 1 . .
H H11A 0.984175 0.562679 0.353691 0.099 Uiso calc 1 . .
H H11B 1.219945 0.488307 0.366534 0.099 Uiso calc 1 . .
H H11C 1.165792 0.610173 0.236291 0.099 Uiso calc 1 . .
C C12 1.2214(6) 0.3751(4) 0.2060(4) 0.0735(11) Uani d 1 . .
H H12A 1.277779 0.453031 0.129752 0.110 Uiso calc 1 . .
H H12B 1.336465 0.334007 0.260380 0.110 Uiso calc 1 . .
H H12C 1.171636 0.306594 0.185095 0.110 Uiso calc 1 . .
C C13 0.3526(7) -0.0550(4) 0.6784(4) 0.0762(10) Uani d 1 . .
H H13A 0.230783 -0.116751 0.712468 0.114 Uiso calc 1 . .
H H13B 0.297175 0.039974 0.636992 0.114 Uiso calc 1 . .
H H13C 0.449045 -0.077743 0.618279 0.114 Uiso calc 1 . .
N N1 0.7287(4) 0.1062(2) 0.6302(2) 0.0503(6) Uani d 1 . .
N N2 0.7550(4) 0.3273(2) 0.4621(2) 0.0441(6) Uani d 1 . .
O O1 1.0292(3) 0.1835(2) 0.4296(2) 0.0567(6) Uani d 1 . .
S S1 0.42204(13) 0.29558(7) 0.64054(7) 0.0537(3) Uani d 1 . .
H H1N 0.841(4) 0.084(4) 0.592(3) 0.064 Uiso d 1 . .
H H2N 0.703(6) 0.411(2) 0.434(3) 0.064 Uiso 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 0.066(2) 0.0377(14) 0.0473(16) 0.0103(13) 0.0110(14) -0.0129(12)
C2 0.066(2) 0.0470(16) 0.0556(18) 0.0094(15) 0.0014(15) -0.0217(14)
C3 0.084(3) 0.0492(18) 0.057(2) 0.0141(17) 0.0096(18) -0.0166(16)
C4 0.094(3) 0.062(2) 0.055(2) 0.016(2) 0.007(2) -0.0182(17)
C5 0.108(3) 0.074(2) 0.0485(17) 0.021(2) -0.0178(19) -0.0174(15)
C6 0.093(3) 0.061(2) 0.0482(16) 0.0275(18) -0.0149(17) -0.0186(13)
C7 0.0446(14) 0.0353(13) 0.0340(13) 0.0004(11) 0.0000(11) -0.0106(10)
C8 0.0368(13) 0.0431(14) 0.0385(14) -0.0004(11) -0.0010(11) -0.0161(11)
C9 0.0429(14) 0.0396(14) 0.0414(14) -0.0011(11) 0.0065(11) -0.0139(11)
C10 0.072(2) 0.064(2) 0.0398(16) 0.0038(17) -0.0042(15) -0.0138(15)
C11 0.059(2) 0.061(2) 0.076(2) -0.0176(16) 0.0085(17) -0.0317(18)
C12 0.069(2) 0.061(2) 0.066(2) 0.0026(17) 0.0296(17) -0.0180(17)
C13 0.082(3) 0.065(2) 0.074(2) -0.0051(19) -0.004(2) -0.0240(19)
N1 0.0527(14) 0.0404(12) 0.0407(13) 0.0072(11) 0.0092(11) -0.0088(10)
N2 0.0442(12) 0.0354(11) 0.0394(12) 0.0033(9) 0.0058(10) -0.0088(10)
O1 0.0537(12) 0.0438(11) 0.0547(12) 0.0094(9) 0.0079(10) -0.0123(9)
S1 0.0573(5) 0.0395(4) 0.0482(4) 0.0048(3) 0.0144(3) -0.0124(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'
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 . . 122.8(3) ?
C2 C1 N1 . . 120.5(3) ?
C6 C1 N1 . . 116.7(3) ?
C1 C2 C13 . . 121.8(3) ?
C1 C2 C3 . . 117.1(3) ?
C13 C2 C3 . . 121.1(4) ?
C4 C3 C2 . . 119.7(4) ?
C4 C3 H3 . . 120.2 ?
C2 C3 H3 . . 120.2 ?
C3 C4 C5 . . 123.2(4) ?
C3 C4 H4 . . 118.4 ?
C5 C4 H4 . . 118.4 ?
C4 C5 C6 . . 119.4(4) ?
C4 C5 H5 . . 120.3 ?
C6 C5 H5 . . 120.3 ?
C5 C6 C1 . . 117.9(4) ?
C5 C6 H6 . . 121.0 ?
C1 C6 H6 . . 121.0 ?
N1 C7 N2 . . 116.4(2) ?
N1 C7 S1 . . 124.4(2) ?
N2 C7 S1 . . 119.26(19) ?
O1 C8 N2 . . 121.7(2) ?
O1 C8 C9 . . 122.8(2) ?
N2 C8 C9 . . 115.5(2) ?
C12 C9 C8 . . 108.6(2) ?
C12 C9 C11 . . 110.0(3) ?
C8 C9 C11 . . 108.3(2) ?
C12 C9 C10 . . 109.5(3) ?
C8 C9 C10 . . 109.9(2) ?
C11 C9 C10 . . 110.5(3) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C9 C11 H11A . . 109.5 ?
C9 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C9 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C9 C12 H12A . . 109.5 ?
C9 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C9 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C2 C13 H13A . . 109.5 ?
C2 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C2 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C7 N1 C1 . . 123.3(2) ?
C7 N1 H1N . . 119(2) ?
C1 N1 H1N . . 117(2) ?
C8 N2 C7 . . 128.5(2) ?
C8 N2 H2N . . 118(2) ?
C7 N2 H2N . . 114(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 . 1.353(5) ?
C1 C6 . 1.424(5) ?
C1 N1 . 1.448(4) ?
C2 C13 . 1.430(5) ?
C2 C3 . 1.436(5) ?
C3 C4 . 1.350(6) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.358(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 N1 . 1.329(3) ?
C7 N2 . 1.393(3) ?
C7 S1 . 1.665(3) ?
C8 O1 . 1.218(3) ?
C8 N2 . 1.381(3) ?
C8 C9 . 1.525(4) ?
C9 C12 . 1.521(4) ?
C9 C11 . 1.529(4) ?
C9 C10 . 1.536(4) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 0.9600 ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N1 H1N . 0.840(18) ?
N2 H2N . 0.852(18) ?
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 O1 . 0.840(18) 1.98(3) 2.644(3) 135(3) yes
C11 H11A S1 2_666 0.96 2.79 3.663(4) 152.00 yes
C12 H12C Cg1 2_756 0.96 2.92 3.640(5) 133 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 C13 . . . . -177.3(3) ?
N1 C1 C2 C13 . . . . 1.3(5) ?
C6 C1 C2 C3 . . . . 1.2(4) ?
N1 C1 C2 C3 . . . . 179.8(3) ?
C1 C2 C3 C4 . . . . -0.8(5) ?
C13 C2 C3 C4 . . . . 177.7(3) ?
C2 C3 C4 C5 . . . . -0.6(6) ?
C3 C4 C5 C6 . . . . 1.6(6) ?
C4 C5 C6 C1 . . . . -1.1(5) ?
C2 C1 C6 C5 . . . . -0.3(5) ?
N1 C1 C6 C5 . . . . -178.9(3) ?
O1 C8 C9 C12 . . . . 4.4(4) ?
N2 C8 C9 C12 . . . . -175.6(3) ?
O1 C8 C9 C11 . . . . -115.0(3) ?
N2 C8 C9 C11 . . . . 65.0(3) ?
O1 C8 C9 C10 . . . . 124.2(3) ?
N2 C8 C9 C10 . . . . -55.8(3) ?
N2 C7 N1 C1 . . . . 171.6(3) ?
S1 C7 N1 C1 . . . . -9.1(5) ?
C2 C1 N1 C7 . . . . 84.0(4) ?
C6 C1 N1 C7 . . . . -97.4(4) ?
O1 C8 N2 C7 . . . . 3.5(5) ?
C9 C8 N2 C7 . . . . -176.5(3) ?
N1 C7 N2 C8 . . . . -0.8(4) ?
S1 C7 N2 C8 . . . . 179.9(2) ?