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3-[(Furan-2-yl-methyl-idene)amino]-1-(4-methyl-phen-yl)thio-urea.
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PMID:  21522967     Owner:  NLM     Status:  PubMed-not-MEDLINE    
Abstract/OtherAbstract:
There are two independent mol-ecules in the asymmetric unit of the title compound, C(13)H(13)N(3)OS, which was obtained from a condensation reaction of N-(p-tol-yl)hydrazinecarbothio-amide and furfural. The dihedral angles between the mean planes of the tolyl ring and the (furan-2-yl-methyl-ene)hydrazine unit are 39.83 (8) and 48.95 (7)° in the two mol-ecules. The mol-ecules both exhibit an E configuration. In the crystal, inter-molecular N-H⋯N and N-H⋯S hydrogen bonds connect the two independent mol-ecules.
Authors:
Yan-Ling Zhang; Fu-Juan Zhang; Zhi-Hong Xu; Feng-Ling Yang
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Publication Detail:
Type:  Journal Article     Date:  2011-01-08
Journal Detail:
Title:  Acta crystallographica. Section E, Structure reports online     Volume:  67     ISSN:  1600-5368     ISO Abbreviation:  Acta Crystallogr E Struct Rep Online     Publication Date:  2011  
Date Detail:
Created Date:  2011-04-27     Completed Date:  2011-07-14     Revised Date:  2011-11-11    
Medline Journal Info:
Nlm Unique ID:  101089178     Medline TA:  Acta Crystallogr E Struct Rep Online     Country:  England    
Other Details:
Languages:  eng     Pagination:  o275     Citation Subset:  -    
Affiliation:
College of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People's Republic of China.
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Journal ID (nlm-ta): Acta Crystallogr Sect E Struct Rep Online
Journal ID (publisher-id): Acta Cryst. E
ISSN: 1600-5368
Publisher: International Union of Crystallography
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A full version of this article is available from Crystallography Journals Online.© Zhang et al. 2011
open-access:
Received Day: 09 Month: 12 Year: 2010
Accepted Day: 04 Month: 1 Year: 2011
collection publication date: Day: 01 Month: 2 Year: 2011
Electronic publication date: Day: 08 Month: 1 Year: 2011
pmc-release publication date: Day: 08 Month: 1 Year: 2011
Volume: 67 Issue: Pt 2
First Page: o275 Last Page: o275
ID: 3051554
PubMed Id: 21522967
Publisher Id: kp2296
DOI: 10.1107/S1600536811000110
Coden: ACSEBH
Publisher Item Identifier: S1600536811000110

3-[(Furan-2-yl­methyl­idene)amino]-1-(4-methyl­phen­yl)thio­urea Alternate Title:C13H13N3OS
Yan-Ling Zhanga
Fu-Juan Zhanga
Zhi-Hong Xua
Feng-Ling Yanga*
aCollege of Chemistry and Chemical Engineering, Xuchang University, Xuchang, Henan Province 461000, People’s Republic of China
Correspondence: Correspondence e-mail: zhangyanling315@126.com

Related literature

For biological applications of thio­semicarbazones, see: Okabe et al. (1993); Hu et al. (2006). For related structures, see: Zhang et al. (2005); Shan et al. (2006).[Chemical Structure ID: scheme1]


Experimental
Crystal data

  • C13H13N3OS
  • Mr = 259.32
  • Monoclinic,
  • a = 12.9464 (3) Å
  • b = 13.8613 (3) Å
  • c = 16.6155 (5) Å
  • β = 118.028 (2)°
  • V = 2632.01 (12) Å3
  • Z = 8
  • Cu Kα radiation
  • μ = 2.12 mm−1
  • T = 293 K
  • 0.20 × 0.20 × 0.20 mm

Data collection

  • Oxford Diffraction Xcalibur Eos Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) Tmin = 0.677, Tmax = 0.677
  • 19253 measured reflections
  • 4697 independent reflections
  • 3878 reflections with I > 2σ(I)
  • Rint = 0.042

Refinement

  • R[F2 > 2σ(F2)] = 0.043
  • wR(F2) = 0.147
  • S = 1.03
  • 4697 reflections
  • 328 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.


Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000110/kp2296sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000110/kp2296Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report


Notes

fnu1Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2296).

The authors thank the Natural Science Foundation of the Education Department of Henan Province, China (2010B150029), the Science Foundation of Henan Province, China (082300420110) and the Scientific Research Foundation of Xuchang University of Henan Province, China (2009086) for supporting this work.

supplementary crystallographic information
Comment

Thiosemicarbazones have attracted our attention because of their biological applications (Okabe et al., 1993; Hu et al., 2006). A few single-crystal structres (Zhang et al., 2005; Shan et al., 2006) were reported. For understanding their anticancer activity, it is necessary to have detailed information on their molecular geometries. Both molecules of the asymmetric unit (I) (Fig. 1) reveal an E-configuration. these molecules are related by a pseudo-inversion symmetry. The dihedral angles between the mean planes of the tolyl ring and the (furan-2-ylmethylene)hydrazine unit are 39.83 (8) and 48.95 (7)°. A dominant motif in a crystal packing are hydrogen bonded dimers via intermolecular N(2)—H(2)···S(1 A)and N(2 A)—H(2 A)···S(1), interactions (Table 1 and Fig. 1). Intramolecular hydrogen bond N3A-H3A···N1A is observed (Table 1) whereas the other molecule of asymmetric unit does not meet the angle criterium (N-H···N angle is 108 °) for intramolecular hydrogen bond. The value of this angle might be affected by lower accuracy of hydrogen atom position or slight difference between molecular conformations of these two molecules.

Experimental

N-(p-Tolyl)hydrazinecarbothioamide (1.8 g,10 mmol) and furfural (0.96 g, 10 mmol) was dissolved in 95% ethanol (15 mL) and the solution was refluxed for 2.5 h. Fine colourless crystals appeared on cooling. They were filtered and washed by 95% ethanol to give 2.06 g of the title compound in 79.5% yield. Single crystals of (I) were obtained by recrystallisation from acetone.

Refinement

H atoms were placed in calculated positions with C—H = 0.93–0.96 and N—H = 0.86 Å, and refined using a riding model, Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N).

Figures
Crystal data
Data collection
Refinement
Special details
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Atomic displacement parameters (Å2)
Geometric parameters (Å, °)
Hydrogen-bond geometry (Å, °)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.


References
Hu, W.-X., Zhou, W., Xia, C.-N. & Wen, X. (2006). Bioorg. Med. Chem. Lett.16, 2213–2218.
Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680.
Oxford Diffraction (2010). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Shan, S. & Zhang, Y.-L. (2006). Acta Cryst. E62, o2051–o2052.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Zhang, Y.-L., Shan, S. & Xu, D.-J. (2005). Acta Cryst. E61, o1173–o1175.

Figures

[Figure ID: Fap1]
Fig. 1. 

The molecular structure of the title compound, with displacement ellipsoids drawn at 30% probability level. The two molecules of the asymmetric unit are connected by hydrogen bonds N-H···S (dashed lines).



Tables
[TableWrap ID: d1e123]
C13H13N3OS F(000) = 1088
Mr = 259.32 Dx = 1.309 Mg m3
Monoclinic, P21/c Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc Cell parameters from 7546 reflections
a = 12.9464 (3) Å θ = 3.0–72.2°
b = 13.8613 (3) Å µ = 2.12 mm1
c = 16.6155 (5) Å T = 293 K
β = 118.028 (2)° Prismatic, colorless
V = 2632.01 (12) Å3 0.20 × 0.20 × 0.20 mm
Z = 8

[TableWrap ID: d1e251]
Oxford Diffraction Xcalibur Eos Gemini diffractometer 4697 independent reflections
Radiation source: fine-focus sealed tube 3878 reflections with I > 2σ(I)
graphite Rint = 0.042
ω scans θmax = 67.1°, θmin = 3.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) h = −15→15
Tmin = 0.677, Tmax = 0.677 k = −16→16
19253 measured reflections l = −19→13

[TableWrap ID: d1e365]
Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043 H-atom parameters constrained
wR(F2) = 0.147 w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03 (Δ/σ)max = 0.001
4697 reflections Δρmax = 0.19 e Å3
328 parameters Δρmin = −0.24 e Å3
0 restraints Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods Extinction coefficient: 0.0044 (4)

[TableWrap ID: d1e543]
Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

[TableWrap ID: d1e648]
x y z Uiso*/Ueq
S1 0.12468 (5) 0.04591 (4) 0.57517 (3) 0.05268 (19)
S1A 0.30556 (5) 0.53789 (4) 0.36034 (4) 0.0548 (2)
O1 0.63171 (13) 0.26407 (12) 0.80209 (9) 0.0551 (4)
O1A −0.24494 (16) 0.36883 (14) 0.18097 (11) 0.0676 (5)
N1 0.42256 (15) 0.16907 (13) 0.73490 (11) 0.0482 (4)
N1A −0.02089 (16) 0.45411 (12) 0.24339 (12) 0.0466 (4)
N2 0.32088 (16) 0.11669 (14) 0.70435 (12) 0.0526 (4)
H2 0.3089 0.0811 0.7415 0.063*
N2A 0.08617 (16) 0.48994 (14) 0.25989 (11) 0.0488 (4)
H2A 0.0953 0.5122 0.2153 0.059*
N3 0.26010 (16) 0.18718 (14) 0.56597 (12) 0.0534 (4)
H3 0.3172 0.2263 0.5953 0.064*
N3A 0.15430 (16) 0.45539 (14) 0.40998 (12) 0.0516 (4)
H3A 0.0848 0.4331 0.3913 0.062*
C1 0.7393 (2) 0.3023 (2) 0.85542 (18) 0.0656 (6)
H1 0.7772 0.3453 0.8351 0.079*
C1A −0.3614 (3) 0.3434 (2) 0.12705 (19) 0.0734 (7)
H1A −0.4045 0.3037 0.1453 0.088*
C2 0.7830 (2) 0.2704 (2) 0.93994 (16) 0.0684 (7)
H2B 0.8552 0.2864 0.9884 0.082*
C2A −0.4018 (2) 0.3844 (2) 0.04573 (17) 0.0697 (7)
H2AA −0.4772 0.3789 −0.0025 0.084*
C3 0.6988 (2) 0.20724 (19) 0.94272 (15) 0.0600 (6)
H3B 0.7047 0.1737 0.9932 0.072*
C3A −0.3098 (2) 0.43732 (19) 0.04610 (15) 0.0568 (5)
H3AA −0.3126 0.4738 −0.0019 0.068*
C4 0.60805 (18) 0.20553 (15) 0.85729 (13) 0.0456 (4)
C4A −0.2166 (2) 0.42593 (15) 0.12823 (14) 0.0488 (5)
C5 0.49801 (19) 0.15645 (15) 0.81887 (13) 0.0478 (5)
H5 0.4809 0.1150 0.8550 0.057*
C5A −0.10118 (19) 0.46325 (15) 0.16071 (14) 0.0475 (5)
H5A −0.0833 0.4958 0.1199 0.057*
C6 0.23996 (18) 0.12135 (15) 0.61564 (13) 0.0457 (4)
C6A 0.17739 (18) 0.49072 (14) 0.34471 (13) 0.0434 (4)
C7 0.19719 (18) 0.19935 (14) 0.46945 (14) 0.0468 (4)
C7A 0.22866 (19) 0.45001 (15) 0.50532 (14) 0.0463 (5)
C8 0.2592 (2) 0.20326 (18) 0.42067 (16) 0.0570 (5)
H8 0.3405 0.1996 0.4512 0.068*
C8A 0.1803 (2) 0.4686 (2) 0.56153 (17) 0.0674 (7)
H8A 0.1016 0.4851 0.5362 0.081*
C9 0.2013 (2) 0.21261 (18) 0.32708 (17) 0.0622 (6)
H9 0.2443 0.2155 0.2954 0.075*
C9A 0.2462 (3) 0.4631 (2) 0.65487 (17) 0.0696 (7)
H9A 0.2114 0.4764 0.6915 0.084*
C10 0.0806 (2) 0.21771 (16) 0.27934 (15) 0.0572 (6)
C10A 0.3629 (2) 0.43844 (17) 0.69498 (15) 0.0535 (5)
C11 0.0199 (2) 0.21777 (18) 0.32891 (16) 0.0602 (6)
H11A −0.0612 0.2233 0.2983 0.072*
C11A 0.41067 (19) 0.41712 (16) 0.63797 (14) 0.0508 (5)
H11 0.4888 0.3987 0.6634 0.061*
C12 0.07673 (19) 0.20985 (17) 0.42347 (15) 0.0550 (5)
H12A 0.0341 0.2116 0.4555 0.066*
C12A 0.34502 (19) 0.42261 (16) 0.54403 (14) 0.0485 (5)
H12 0.3790 0.4079 0.5071 0.058*
C13 0.0164 (3) 0.2217 (2) 0.17613 (17) 0.0784 (8)
H13D 0.0540 0.2675 0.1551 0.118*
H13E −0.0632 0.2410 0.1560 0.118*
H13F 0.0177 0.1591 0.1519 0.118*
C13A 0.4365 (3) 0.4347 (2) 0.79706 (17) 0.0710 (7)
H13A 0.3925 0.4598 0.8255 0.106*
H13B 0.5058 0.4728 0.8149 0.106*
H13C 0.4581 0.3691 0.8159 0.106*

[TableWrap ID: d1e1463]
U11 U22 U33 U12 U13 U23
S1 0.0500 (3) 0.0630 (3) 0.0400 (3) −0.0190 (2) 0.0169 (2) −0.0050 (2)
S1A 0.0495 (3) 0.0691 (4) 0.0465 (3) −0.0145 (2) 0.0231 (2) −0.0043 (2)
O1 0.0478 (8) 0.0680 (10) 0.0420 (7) −0.0072 (7) 0.0149 (6) 0.0030 (6)
O1A 0.0630 (11) 0.0806 (12) 0.0538 (9) −0.0012 (9) 0.0230 (8) 0.0119 (8)
N1 0.0433 (9) 0.0527 (9) 0.0410 (8) −0.0064 (7) 0.0135 (7) −0.0019 (7)
N1A 0.0440 (9) 0.0521 (9) 0.0412 (9) 0.0009 (7) 0.0178 (8) 0.0003 (7)
N2 0.0482 (10) 0.0609 (10) 0.0411 (9) −0.0140 (8) 0.0148 (8) 0.0005 (7)
N2A 0.0448 (9) 0.0615 (10) 0.0390 (8) −0.0020 (8) 0.0188 (7) 0.0046 (7)
N3 0.0454 (9) 0.0605 (11) 0.0422 (9) −0.0160 (8) 0.0107 (7) 0.0014 (7)
N3A 0.0401 (9) 0.0709 (12) 0.0401 (9) −0.0100 (8) 0.0156 (8) 0.0018 (7)
C1 0.0520 (13) 0.0771 (16) 0.0630 (14) −0.0173 (12) 0.0232 (11) −0.0052 (12)
C1A 0.0677 (16) 0.0854 (18) 0.0701 (16) −0.0179 (14) 0.0349 (14) 0.0011 (14)
C2 0.0456 (12) 0.0907 (19) 0.0490 (12) −0.0128 (12) 0.0056 (10) −0.0063 (12)
C2A 0.0501 (13) 0.0953 (19) 0.0528 (13) −0.0161 (13) 0.0151 (11) −0.0055 (12)
C3 0.0540 (13) 0.0713 (14) 0.0393 (10) −0.0026 (11) 0.0091 (9) 0.0042 (10)
C3A 0.0462 (12) 0.0749 (14) 0.0402 (10) −0.0061 (11) 0.0127 (9) 0.0084 (10)
C4 0.0442 (11) 0.0475 (10) 0.0390 (10) 0.0015 (8) 0.0145 (8) −0.0006 (8)
C4A 0.0487 (11) 0.0518 (11) 0.0423 (10) 0.0035 (9) 0.0183 (9) −0.0001 (8)
C5 0.0480 (11) 0.0466 (10) 0.0431 (10) −0.0004 (9) 0.0168 (9) 0.0010 (8)
C5A 0.0450 (11) 0.0540 (11) 0.0390 (10) 0.0036 (8) 0.0161 (9) 0.0031 (8)
C6 0.0438 (10) 0.0498 (10) 0.0411 (10) −0.0050 (8) 0.0181 (8) −0.0058 (8)
C6A 0.0444 (10) 0.0465 (10) 0.0398 (9) 0.0004 (8) 0.0201 (8) −0.0028 (8)
C7 0.0434 (10) 0.0448 (10) 0.0435 (10) −0.0038 (8) 0.0132 (9) 0.0027 (8)
C7A 0.0431 (10) 0.0542 (11) 0.0392 (10) −0.0071 (8) 0.0172 (9) −0.0004 (8)
C8 0.0431 (11) 0.0670 (14) 0.0569 (12) 0.0036 (10) 0.0203 (10) 0.0062 (10)
C8A 0.0452 (12) 0.109 (2) 0.0491 (13) 0.0111 (12) 0.0232 (11) 0.0067 (12)
C9 0.0703 (15) 0.0666 (14) 0.0552 (13) 0.0088 (12) 0.0341 (12) 0.0059 (11)
C9A 0.0627 (15) 0.105 (2) 0.0467 (13) 0.0066 (14) 0.0306 (12) 0.0004 (12)
C10 0.0662 (14) 0.0475 (11) 0.0450 (11) 0.0019 (10) 0.0155 (10) 0.0034 (9)
C10A 0.0554 (13) 0.0565 (12) 0.0429 (11) −0.0058 (10) 0.0183 (10) −0.0015 (9)
C11 0.0450 (12) 0.0625 (13) 0.0554 (13) −0.0003 (10) 0.0090 (10) 0.0104 (10)
C11A 0.0441 (11) 0.0530 (11) 0.0490 (11) 0.0009 (9) 0.0166 (9) 0.0041 (9)
C12 0.0434 (11) 0.0656 (13) 0.0532 (12) −0.0014 (10) 0.0204 (10) 0.0076 (10)
C12A 0.0465 (11) 0.0553 (11) 0.0440 (10) 0.0015 (9) 0.0217 (9) 0.0022 (8)
C13 0.095 (2) 0.0716 (16) 0.0469 (13) 0.0048 (15) 0.0153 (13) 0.0059 (11)
C13A 0.0754 (17) 0.0839 (17) 0.0437 (12) −0.0012 (14) 0.0197 (12) −0.0006 (11)

[TableWrap ID: d1e2123]
S1—C6 1.682 (2) C4—C5 1.430 (3)
S1A—C6A 1.686 (2) C4A—C5A 1.427 (3)
O1—C1 1.359 (3) C5—H5 0.9300
O1—C4 1.363 (3) C5A—H5A 0.9300
O1A—C4A 1.353 (3) C7—C12 1.385 (3)
O1A—C1A 1.389 (3) C7—C8 1.385 (3)
N1—C5 1.285 (3) C7A—C8A 1.371 (3)
N1—N2 1.375 (2) C7A—C12A 1.384 (3)
N1A—C5A 1.281 (3) C8—C9 1.379 (3)
N1A—N2A 1.373 (2) C8—H8 0.9300
N2—C6 1.350 (3) C8A—C9A 1.377 (4)
N2—H2 0.8599 C8A—H8A 0.9300
N2A—C6A 1.348 (3) C9—C10 1.382 (4)
N2A—H2A 0.8600 C9—H9 0.9300
N3—C6 1.336 (3) C9A—C10A 1.377 (4)
N3—C7 1.427 (3) C9A—H9A 0.9300
N3—H3 0.8600 C10—C11 1.380 (4)
N3A—C6A 1.345 (3) C10—C13 1.515 (3)
N3A—C7A 1.417 (3) C10A—C11A 1.385 (3)
N3A—H3A 0.8600 C10A—C13A 1.506 (3)
C1—C2 1.320 (4) C11—C12 1.391 (3)
C1—H1 0.9300 C11—H11A 0.9300
C1A—C2A 1.326 (4) C11A—C12A 1.385 (3)
C1A—H1A 0.9300 C11A—H11 0.9300
C2—C3 1.415 (4) C12—H12A 0.9300
C2—H2B 0.9300 C12A—H12 0.9300
C2A—C3A 1.397 (3) C13—H13D 0.9600
C2A—H2AA 0.9300 C13—H13E 0.9600
C3—C4 1.352 (3) C13—H13F 0.9600
C3—H3B 0.9300 C13A—H13A 0.9600
C3A—C4A 1.340 (3) C13A—H13B 0.9600
C3A—H3AA 0.9300 C13A—H13C 0.9600
C1—O1—C4 106.22 (18) N3A—C6A—S1A 126.32 (16)
C4A—O1A—C1A 105.83 (19) N2A—C6A—S1A 118.65 (15)
C5—N1—N2 115.88 (17) C12—C7—C8 119.1 (2)
C5A—N1A—N2A 114.36 (17) C12—C7—N3 122.2 (2)
C6—N2—N1 119.67 (17) C8—C7—N3 118.73 (19)
C6—N2—H2 120.2 C8A—C7A—C12A 118.7 (2)
N1—N2—H2 120.1 C8A—C7A—N3A 117.6 (2)
C6A—N2A—N1A 121.19 (16) C12A—C7A—N3A 123.58 (19)
C6A—N2A—H2A 119.4 C9—C8—C7 120.4 (2)
N1A—N2A—H2A 119.5 C9—C8—H8 119.8
C6—N3—C7 126.95 (18) C7—C8—H8 119.8
C6—N3—H3 116.5 C7A—C8A—C9A 121.1 (2)
C7—N3—H3 116.5 C7A—C8A—H8A 119.4
C6A—N3A—C7A 128.95 (18) C9A—C8A—H8A 119.4
C6A—N3A—H3A 115.5 C8—C9—C10 121.4 (2)
C7A—N3A—H3A 115.5 C8—C9—H9 119.3
C2—C1—O1 111.0 (2) C10—C9—H9 119.3
C2—C1—H1 124.5 C10A—C9A—C8A 121.2 (2)
O1—C1—H1 124.5 C10A—C9A—H9A 119.4
C2A—C1A—O1A 109.7 (2) C8A—C9A—H9A 119.4
C2A—C1A—H1A 125.1 C11—C10—C9 117.7 (2)
O1A—C1A—H1A 125.1 C11—C10—C13 120.8 (2)
C1—C2—C3 106.9 (2) C9—C10—C13 121.5 (3)
C1—C2—H2B 126.5 C9A—C10A—C11A 117.6 (2)
C3—C2—H2B 126.5 C9A—C10A—C13A 121.6 (2)
C1A—C2A—C3A 107.0 (2) C11A—C10A—C13A 120.9 (2)
C1A—C2A—H2AA 126.5 C10—C11—C12 121.8 (2)
C3A—C2A—H2AA 126.5 C10—C11—H11A 119.1
C4—C3—C2 106.2 (2) C12—C11—H11A 119.1
C4—C3—H3B 126.9 C12A—C11A—C10A 121.6 (2)
C2—C3—H3B 126.9 C12A—C11A—H11 119.2
C4A—C3A—C2A 107.5 (2) C10A—C11A—H11 119.2
C4A—C3A—H3AA 126.3 C7—C12—C11 119.5 (2)
C2A—C3A—H3AA 126.3 C7—C12—H12A 120.3
C3—C4—O1 109.7 (2) C11—C12—H12A 120.3
C3—C4—C5 132.0 (2) C7A—C12A—C11A 119.75 (19)
O1—C4—C5 118.33 (17) C7A—C12A—H12 120.1
C3A—C4A—O1A 109.9 (2) C11A—C12A—H12 120.1
C3A—C4A—C5A 128.6 (2) C10—C13—H13D 109.5
O1A—C4A—C5A 121.45 (19) C10—C13—H13E 109.5
N1—C5—C4 120.63 (19) H13D—C13—H13E 109.5
N1—C5—H5 119.7 C10—C13—H13F 109.5
C4—C5—H5 119.7 H13D—C13—H13F 109.5
N1A—C5A—C4A 123.2 (2) H13E—C13—H13F 109.5
N1A—C5A—H5A 118.4 C10A—C13A—H13A 109.5
C4A—C5A—H5A 118.4 C10A—C13A—H13B 109.5
N3—C6—N2 115.50 (18) H13A—C13A—H13B 109.5
N3—C6—S1 124.88 (16) C10A—C13A—H13C 109.5
N2—C6—S1 119.62 (16) H13A—C13A—H13C 109.5
N3A—C6A—N2A 115.00 (18) H13B—C13A—H13C 109.5
C5—N1—N2—C6 −176.10 (19) C7A—N3A—C6A—S1A 0.8 (3)
C5A—N1A—N2A—C6A 176.01 (19) N1A—N2A—C6A—N3A −0.8 (3)
C4—O1—C1—C2 0.2 (3) N1A—N2A—C6A—S1A −178.76 (15)
C4A—O1A—C1A—C2A −0.7 (3) C6—N3—C7—C12 53.4 (3)
O1—C1—C2—C3 −0.2 (3) C6—N3—C7—C8 −128.4 (3)
O1A—C1A—C2A—C3A 0.3 (4) C6A—N3A—C7A—C8A 140.9 (3)
C1—C2—C3—C4 0.1 (3) C6A—N3A—C7A—C12A −42.4 (3)
C1A—C2A—C3A—C4A 0.2 (3) C12—C7—C8—C9 −3.2 (4)
C2—C3—C4—O1 0.0 (3) N3—C7—C8—C9 178.4 (2)
C2—C3—C4—C5 −178.9 (2) C12A—C7A—C8A—C9A 2.0 (4)
C1—O1—C4—C3 −0.1 (3) N3A—C7A—C8A—C9A 178.8 (3)
C1—O1—C4—C5 179.0 (2) C7—C8—C9—C10 −0.4 (4)
C2A—C3A—C4A—O1A −0.6 (3) C7A—C8A—C9A—C10A −0.3 (5)
C2A—C3A—C4A—C5A 177.9 (2) C8—C9—C10—C11 3.0 (4)
C1A—O1A—C4A—C3A 0.8 (3) C8—C9—C10—C13 −176.1 (2)
C1A—O1A—C4A—C5A −177.9 (2) C8A—C9A—C10A—C11A −1.5 (4)
N2—N1—C5—C4 178.51 (19) C8A—C9A—C10A—C13A 178.5 (3)
C3—C4—C5—N1 177.4 (2) C9—C10—C11—C12 −2.1 (4)
O1—C4—C5—N1 −1.5 (3) C13—C10—C11—C12 177.1 (2)
N2A—N1A—C5A—C4A 176.32 (19) C9A—C10A—C11A—C12A 1.6 (4)
C3A—C4A—C5A—N1A 174.2 (2) C13A—C10A—C11A—C12A −178.3 (2)
O1A—C4A—C5A—N1A −7.4 (3) C8—C7—C12—C11 4.1 (3)
C7—N3—C6—N2 171.9 (2) N3—C7—C12—C11 −177.6 (2)
C7—N3—C6—S1 −7.4 (3) C10—C11—C12—C7 −1.5 (4)
N1—N2—C6—N3 −7.8 (3) C8A—C7A—C12A—C11A −1.8 (3)
N1—N2—C6—S1 171.49 (16) N3A—C7A—C12A—C11A −178.48 (19)
C7A—N3A—C6A—N2A −177.0 (2) C10A—C11A—C12A—C7A 0.0 (3)

[TableWrap ID: d1e3194]
D—H···A D—H H···A D···A D—H···A
N2—H2···S1Ai 0.86 2.59 3.4397 (19) 171
N2A—H2A···S1ii 0.86 2.66 3.3696 (17) 141
N3A—H3A···N1A 0.86 2.20 2.628 (2) 111


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