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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o482.
Published online 2009 February 6. doi:  10.1107/S1600536809003146
PMCID: PMC2968578

1,3-Bis(3-methyl­phen­yl)thio­urea: triclinic polymorph

Abstract

The title compound, C15H16N2S, crystallizes with two molecules in the asymmetric unit. The crystallographic behaviour of the two isomers is different. The mol­ecules are dimerized, forming an R 2 2(8) ring motif due to inter­molecular N—H(...)S hydrogen bonds. C—H(...)S hydrogen bonds form R 2 2(12) ring motifs. In one molecule, the dihedral angle between the benzene rings is 62.54 (6)°, whereas in the other it is 79.54 (6)°. The H atoms of one of the methyl groups in each molecule are disordered over two sites, with occupancy ratios of 0.52 (3):0.48 (3) and 0.60 (3):0.40 (3).

Related literature

For general background, see: Chen et al. (2006 [triangle]). For a report of the title compound in the monoclinic crystal system, see: Soriano-Garcia et al. (2003 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o482-scheme1.jpg

Experimental

Crystal data

  • C15H16N2S
  • M r = 256.36
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o482-efi1.jpg
  • a = 10.0483 (5) Å
  • b = 12.0993 (7) Å
  • c = 13.1100 (7) Å
  • α = 67.633 (2)°
  • β = 73.496 (1)°
  • γ = 74.994 (2)°
  • V = 1392.64 (13) Å3
  • Z = 4
  • Mo Kα radiation radiation
  • μ = 0.22 mm−1
  • T = 296 (2) K
  • 0.25 × 0.14 × 0.10 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.960, T max = 0.982
  • 31605 measured reflections
  • 7452 independent reflections
  • 4540 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047
  • wR(F 2) = 0.116
  • S = 1.00
  • 7452 reflections
  • 332 parameters
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]) and PLATON.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003146/at2714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003146/at2714Isup2.hkl

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

Acknowledgments

MAK gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing him with a Scholarship under the Indigenous PhD Programme (PIN 042-121799-PS2-35).

supplementary crystallographic information

Comment

Bisthiourea analogs have attracted wide attention in recent years on account of their versatile applications ranging; catalysis, biological activity and sophisticate optical technology. Their Palladium complexes have been reported as efficient catalysts for Heck and Suzuki coupling reactions (Chen et al., 2006). The title compound (I), (Fig. 1) is one of the series of bisthioureas synthesized for further complexation and organic derivatization.

Soriano-Garcia et al. (2003) has published the crystal structure of the title compound with monoclinic crystal system. In the reported structure the methyl groups are oriented in cis form. The title compound (I) crystallizes in triclinic crystal system with two chemically equivalant asymmetric units having minor differences in bond distances and bond angles. In this compound the methyl groups are almost in trans forms. The major difference in the two chemical units of (I) is of the dihederal angles between the benzene rings. The ring A (C1–C6) is oriented at an angle of 62.54 (6)° with the ring B (C9–C14) in one molecule, whereas the same between the ring C (C16–C21) and ring D (C24–C29) is 79.54 (6)°. Although the moieties around S═O bonds are similar as far as chemistry is concerned, but they behave differently in forming ring motifs. There exist only intermolecular H-bonds (Table 1). The hydrogen bonds of type N—H···S form R22(8) (Bernstein et al., 1995), whereas H-bonds of type C—H···S make R22(12) ring motifs (Fig. 2). The H atoms of one of methyl groups in each chemical units are disordered over two sites with occupancies ratios 0.52 (3):0.48 (3) and 0.60 (3):0.40 (3).

Experimental

The title compound was prepared by adding CS2 dropwise in m-toluidine (2 g, 0.0187 mol) dissolved in alkaline (NaOH; 0.75 g, 0.0187 mol) ethanol (95% aq.) while stirring continuously at room temperature for one hour. The precipitated product was filtered and recrystallized from warm methanol.

Refinement

H atoms were positioned geometrically, with N—H = 0.86 Å, C—H = 0.93 and 0.96 Å for aromatic and methyl H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C, N), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Figures

Fig. 1.
ORTEP drawing of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H atoms are shown by small circles of arbitrary radii.
Fig. 2.
The partial packing figure (PLATON: Spek, 2003) which shows that intermolecular H-bonds form the ring motifs.

Crystal data

C15H16N2SZ = 4
Mr = 256.36F(000) = 544
Triclinic, P1Dx = 1.233 Mg m3
Hall symbol: -P 1Mo Kα radiation radiation, λ = 0.71073 Å
a = 10.0483 (5) ÅCell parameters from 7452 reflections
b = 12.0993 (7) Åθ = 2.5–29.1°
c = 13.1100 (7) ŵ = 0.22 mm1
α = 67.633 (2)°T = 296 K
β = 73.496 (1)°Needle, colourless
γ = 74.994 (2)°0.25 × 0.14 × 0.10 mm
V = 1392.64 (13) Å3

Data collection

Bruker Kappa APEXII CCD diffractometer7452 independent reflections
Radiation source: fine-focus sealed tube4540 reflections with I > 2σ(I)
graphiteRint = 0.042
Detector resolution: 7.40 pixels mm-1θmax = 29.1°, θmin = 2.5°
ω scansh = −13→12
Absorption correction: multi-scan (SADABS; Bruker, 2005)k = −16→16
Tmin = 0.960, Tmax = 0.982l = −17→17
31605 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.116w = 1/[σ2(Fo2) + (0.0448P)2 + 0.2934P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
7452 reflectionsΔρmax = 0.30 e Å3
332 parametersΔρmin = −0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0096 (12)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
S11.22719 (4)0.05439 (4)−0.03732 (4)0.0398 (1)
N11.07002 (14)0.04399 (14)0.16375 (11)0.0427 (5)
N20.99190 (16)0.20068 (14)0.01812 (12)0.0535 (5)
C10.95406 (17)0.07128 (15)0.24821 (13)0.0365 (5)
C20.81844 (17)0.06802 (16)0.24622 (14)0.0396 (6)
C30.70482 (17)0.09124 (16)0.32960 (15)0.0405 (6)
C40.73165 (19)0.11622 (17)0.41577 (15)0.0444 (6)
C50.8671 (2)0.11785 (18)0.41887 (15)0.0474 (6)
C60.97971 (18)0.09560 (16)0.33493 (14)0.0424 (6)
C70.55815 (10)0.08570 (18)0.32691 (8)0.0637 (8)
C81.08837 (9)0.10228 (10)0.05234 (9)0.0352 (5)
C90.98934 (9)0.27754 (9)−0.09582 (8)0.0422 (6)
C101.06849 (9)0.36925 (9)−0.14583 (9)0.0462 (6)
C111.06095 (19)0.44879 (17)−0.25359 (17)0.0512 (7)
C120.9708 (2)0.4346 (2)−0.30793 (17)0.0581 (7)
C130.8915 (2)0.3441 (2)−0.25806 (19)0.0642 (8)
C140.9009 (2)0.26440 (19)−0.15136 (18)0.0565 (7)
C151.1498 (3)0.5470 (2)−0.3100 (2)0.0904 (10)
S20.68029 (5)0.12464 (5)0.70426 (4)0.0523 (2)
N30.42439 (14)0.25189 (14)0.74526 (11)0.0406 (5)
N40.54748 (14)0.18299 (13)0.88624 (11)0.0390 (5)
C160.40038 (17)0.27933 (15)0.63565 (14)0.0361 (5)
C170.28808 (18)0.24203 (16)0.62503 (15)0.0417 (6)
C180.2573 (2)0.27196 (17)0.51940 (17)0.0471 (6)
C190.3421 (2)0.34043 (19)0.42651 (17)0.0551 (7)
C200.4540 (2)0.3772 (2)0.43720 (16)0.0582 (7)
C210.48483 (19)0.34709 (17)0.54144 (15)0.0465 (6)
C220.13661 (15)0.22770 (16)0.50862 (8)0.0752 (10)
C230.54422 (10)0.19099 (9)0.78139 (10)0.0342 (5)
C240.45749 (9)0.25761 (10)0.94960 (8)0.0372 (6)
C250.43907 (9)0.38272 (10)0.90138 (10)0.0453 (6)
C260.3547 (2)0.4579 (2)0.96132 (18)0.0560 (8)
C270.2899 (2)0.4044 (3)1.0711 (2)0.0670 (9)
C280.3101 (2)0.2805 (3)1.12038 (18)0.0673 (9)
C290.3942 (2)0.2051 (2)1.06051 (15)0.0513 (7)
C300.3375 (3)0.5945 (2)0.9066 (2)0.0873 (11)
H11.13465−0.015970.186720.0513*
H20.802800.049980.188120.0476*
H2A0.925050.219390.069720.0641*
H40.657300.132110.472360.0533*
H50.883150.134040.477860.0569*
H61.070960.097050.337040.0509*
H7A0.492230.110310.386660.0956*0.52 (3)
H7B0.536150.139050.255710.0956*0.52 (3)
H7C0.552410.004190.336640.0956*0.52 (3)
H101.127390.37773−0.106870.0554*
H120.963680.48768−0.380090.0697*
H130.831190.33635−0.296290.0771*
H140.847710.20238−0.117410.0677*
H15A1.176670.56008−0.389480.1357*
H15B1.096760.62071−0.297420.1357*
H15C1.232770.52300−0.278940.1357*
H7D0.560370.067510.261210.0956*0.48 (3)
H7E0.521620.023540.393330.0956*0.48 (3)
H7F0.498800.162510.324470.0956*0.48 (3)
H30.356140.276440.792810.0488*
H4A0.610040.127340.918160.0468*
H170.232110.196370.688980.0500*
H190.322930.362010.355390.0661*
H200.509790.423040.373290.0698*
H210.561120.371930.548280.0557*
H22A0.105770.279580.440280.1128*0.60 (3)
H22B0.060170.228970.571990.1128*0.60 (3)
H22C0.166960.146340.506700.1128*0.60 (3)
H250.484230.417200.827160.0544*
H270.231610.452851.112490.0804*
H280.266600.246471.195200.0807*
H290.407480.121291.094410.0615*
H30A0.420450.615630.850360.1314*
H30B0.323830.631260.962870.1314*
H30C0.257210.623210.871850.1314*
H22D0.117030.156350.571830.1128*0.40 (3)
H22E0.161270.208710.440120.1128*0.40 (3)
H22F0.054610.289830.507020.1128*0.40 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0400 (2)0.0445 (3)0.0306 (2)−0.0015 (2)−0.0038 (2)−0.0139 (2)
N10.0417 (8)0.0467 (9)0.0287 (8)0.0065 (7)−0.0063 (6)−0.0104 (7)
N20.0526 (9)0.0506 (10)0.0310 (8)0.0121 (7)0.0005 (7)−0.0054 (7)
C10.0423 (9)0.0339 (10)0.0263 (9)−0.0025 (7)−0.0044 (7)−0.0071 (7)
C20.0480 (9)0.0417 (11)0.0308 (9)−0.0035 (8)−0.0109 (7)−0.0145 (8)
C30.0413 (9)0.0392 (10)0.0355 (10)−0.0033 (7)−0.0061 (7)−0.0100 (8)
C40.0497 (10)0.0446 (11)0.0338 (10)−0.0032 (8)−0.0004 (8)−0.0166 (9)
C50.0614 (11)0.0514 (12)0.0337 (10)−0.0116 (9)−0.0078 (8)−0.0190 (9)
C60.0455 (9)0.0466 (11)0.0365 (10)−0.0093 (8)−0.0094 (8)−0.0136 (9)
C70.0452 (11)0.0781 (16)0.0662 (15)−0.0067 (10)−0.0091 (10)−0.0263 (13)
C80.0380 (8)0.0363 (10)0.0299 (9)−0.0057 (7)−0.0061 (7)−0.0104 (8)
C90.0407 (9)0.0372 (10)0.0350 (10)0.0023 (8)−0.0045 (7)−0.0053 (8)
C100.0377 (9)0.0457 (12)0.0511 (12)−0.0015 (8)−0.0130 (8)−0.0127 (10)
C110.0444 (10)0.0380 (11)0.0558 (13)−0.0039 (8)−0.0068 (9)−0.0034 (10)
C120.0638 (12)0.0516 (13)0.0429 (12)0.0008 (10)−0.0172 (10)−0.0009 (10)
C130.0703 (14)0.0669 (16)0.0596 (14)−0.0166 (12)−0.0275 (11)−0.0121 (12)
C140.0627 (12)0.0491 (13)0.0544 (13)−0.0198 (10)−0.0118 (10)−0.0072 (11)
C150.0785 (17)0.0647 (17)0.102 (2)−0.0291 (14)−0.0176 (15)0.0108 (15)
S20.0482 (3)0.0674 (4)0.0376 (3)0.0154 (2)−0.0142 (2)−0.0259 (3)
N30.0342 (7)0.0573 (10)0.0293 (8)0.0024 (6)−0.0083 (6)−0.0186 (7)
N40.0404 (7)0.0451 (9)0.0316 (8)0.0042 (6)−0.0145 (6)−0.0151 (7)
C160.0399 (8)0.0354 (10)0.0317 (9)0.0032 (7)−0.0125 (7)−0.0125 (8)
C170.0466 (9)0.0367 (10)0.0408 (10)−0.0026 (8)−0.0165 (8)−0.0093 (8)
C180.0605 (11)0.0353 (10)0.0516 (12)0.0036 (9)−0.0310 (10)−0.0149 (9)
C190.0727 (13)0.0548 (13)0.0370 (11)0.0057 (10)−0.0279 (10)−0.0132 (10)
C200.0630 (12)0.0622 (14)0.0352 (11)−0.0087 (10)−0.0095 (9)−0.0026 (10)
C210.0480 (10)0.0483 (12)0.0386 (11)−0.0088 (9)−0.0125 (8)−0.0066 (9)
C220.0942 (17)0.0619 (15)0.0879 (18)−0.0124 (13)−0.0588 (15)−0.0166 (14)
C230.0365 (8)0.0362 (10)0.0298 (9)−0.0048 (7)−0.0083 (7)−0.0108 (8)
C240.0361 (8)0.0495 (12)0.0311 (9)−0.0035 (7)−0.0109 (7)−0.0185 (8)
C250.0469 (10)0.0516 (12)0.0381 (10)−0.0008 (8)−0.0124 (8)−0.0179 (9)
C260.0525 (11)0.0621 (14)0.0619 (14)0.0079 (10)−0.0208 (10)−0.0349 (12)
C270.0563 (12)0.0884 (19)0.0671 (16)0.0039 (12)−0.0065 (11)−0.0526 (15)
C280.0688 (14)0.100 (2)0.0393 (12)−0.0276 (14)0.0088 (10)−0.0356 (13)
C290.0627 (12)0.0615 (14)0.0347 (11)−0.0198 (10)−0.0067 (9)−0.0178 (10)
C300.105 (2)0.0608 (16)0.101 (2)0.0215 (14)−0.0380 (16)−0.0435 (15)

Geometric parameters (Å, °)

S1—C81.6827 (12)C10—H100.9300
S2—C231.6734 (13)C12—H120.9300
N1—C81.3398 (17)C13—H130.9300
N1—C11.428 (2)C14—H140.9300
N2—C81.342 (2)C15—H15A0.9600
N2—C91.4314 (17)C15—H15C0.9600
N1—H10.8600C15—H15B0.9600
N2—H2A0.8600C16—C171.377 (3)
N3—C161.423 (2)C16—C211.383 (3)
N3—C231.3476 (19)C17—C181.396 (3)
N4—C231.3500 (18)C18—C191.380 (3)
N4—C241.4297 (19)C18—C221.506 (3)
N3—H30.8600C19—C201.370 (3)
N4—H4A0.8600C20—C211.378 (3)
C1—C61.381 (2)C24—C291.380 (2)
C1—C21.381 (3)C24—C251.3851 (17)
C2—C31.391 (3)C25—C261.389 (3)
C3—C71.503 (2)C26—C271.375 (3)
C3—C41.384 (3)C26—C301.515 (3)
C4—C51.379 (3)C27—C281.373 (5)
C5—C61.387 (3)C28—C291.390 (4)
C9—C141.369 (2)C17—H170.9300
C9—C101.3787 (15)C19—H190.9300
C10—C111.384 (2)C20—H200.9300
C11—C121.378 (3)C21—H210.9300
C11—C151.504 (3)C22—H22A0.9600
C12—C131.368 (3)C22—H22B0.9600
C13—C141.377 (3)C22—H22C0.9600
C2—H20.9300C22—H22D0.9600
C4—H40.9300C22—H22E0.9600
C5—H50.9300C22—H22F0.9600
C6—H60.9300C25—H250.9300
C7—H7F0.9600C27—H270.9300
C7—H7E0.9600C28—H280.9300
C7—H7A0.9600C29—H290.9300
C7—H7D0.9600C30—H30A0.9600
C7—H7C0.9600C30—H30B0.9600
C7—H7B0.9600C30—H30C0.9600
S1···N3i3.4381 (15)H2A···H22.4300
S1···C103.6191 (12)H2A···C12.3900
S1···C29i3.518 (2)H2A···C22.5000
S1···N4ii3.4856 (16)H2A···C30v3.0200
S2···N1ii3.2528 (16)H2A···H30Cv2.4600
S2···C213.306 (2)H3···S1iv3.0800
S1···H2iii2.8300H3···C10iv2.8200
S1···H4Aii2.6300H3···C242.4500
S1···H3i3.0800H3···C252.6400
S1···H14iii3.1400H3···H10iv2.5600
S2···H53.0700H4···S23.0800
S2···H213.0700H4···C203.0900
S2···H1ii2.4600H4···C213.0300
S2···H43.0800H4···H7A2.3700
N1···S2ii3.2528 (16)H4A···S1ii2.6300
N2···C23.065 (2)H5···S23.0700
N3···S1iv3.4381 (15)H7A···H42.3700
N3···C253.078 (2)H7A···C192.9600
N4···S1ii3.4856 (16)H7B···C28ix3.0300
N2···H22.8600H7B···C29ix3.0200
N3···H252.8500H7C···C17vi2.9200
C2···N23.065 (2)H7D···H22.3400
C10···S13.6191 (12)H7E···H7Evi2.5600
C11···C17i3.465 (3)H7F···C192.8500
C12···C17i3.533 (3)H10···H3i2.5600
C17···C12iv3.533 (3)H10···H15C2.4300
C17···C11iv3.465 (3)H12···H22Ax2.5800
C21···S23.306 (2)H12···H22Fx2.5600
C21···C21v3.507 (3)H12···H15A2.4700
C25···N33.078 (2)H14···S1iii3.1400
C29···S1iv3.518 (2)H15A···H122.4700
C1···H22Dvi2.9600H15B···C5vii3.0200
C1···H2A2.3900H15C···H102.4300
C2···H22Dvi2.9200H17···H22B2.4900
C2···H2A2.5000H17···H22D2.4100
C3···H22Cvi3.0800H19···H22A2.4300
C3···H22Dvi3.0700H19···H22E2.5100
C4···H22Cvi2.9400H20···H25v2.6000
C5···H22Cvi3.0500H21···S23.0700
C5···H15Bvii3.0200H21···C232.9900
C8···H23.0000H21···C20v3.0800
C10···H3i2.8200H21···C21v3.1000
C13···H22Bi2.9600H22A···H192.4300
C17···H7Cvi2.9200H22A···H12x2.5800
C19···H7F2.8500H22B···C13iv2.9600
C19···H7A2.9600H22B···H172.4900
C20···H43.0900H22C···C3vi3.0800
C20···H21v3.0800H22C···C4vi2.9400
C21···H21v3.1000H22C···C5vi3.0500
C21···H43.0300H22D···C2vi2.9200
C23···H212.9900H22D···H172.4100
C23···H252.9000H22D···C1vi2.9600
C24···H32.4500H22D···C3vi3.0700
C25···H32.6400H22E···H192.5100
C28···H7Bviii3.0300H22F···H12x2.5600
C29···H7Bviii3.0200H25···N32.8500
C30···H2Av3.0200H25···H20v2.6000
H1···S2ii2.4600H25···C232.9000
H2···N22.8600H25···H30A2.4300
H2···H7D2.3400H27···H30B2.4800
H2···C83.0000H30A···H252.4300
H2···H2A2.4300H30B···H272.4800
H2···S1iii2.8300H30C···H2Av2.4600
C1—N1—C8126.62 (14)H15B—C15—H15C109.00
C8—N2—C9126.40 (13)H15A—C15—H15C109.00
C1—N1—H1117.00C11—C15—H15C109.00
C8—N1—H1117.00C11—C15—H15A110.00
C8—N2—H2A117.00C11—C15—H15B109.00
C9—N2—H2A117.00H15A—C15—H15B109.00
C16—N3—C23126.00 (14)N3—C16—C17119.09 (16)
C23—N4—C24126.62 (13)N3—C16—C21120.47 (17)
C23—N3—H3117.00C17—C16—C21120.38 (16)
C16—N3—H3117.00C16—C17—C18120.77 (17)
C23—N4—H4A117.00C17—C18—C22120.22 (17)
C24—N4—H4A117.00C19—C18—C22121.77 (17)
N1—C1—C2120.51 (15)C17—C18—C19117.99 (19)
C2—C1—C6120.26 (16)C18—C19—C20121.16 (19)
N1—C1—C6119.16 (16)C19—C20—C21120.84 (19)
C1—C2—C3121.17 (16)C16—C21—C20118.85 (19)
C4—C3—C7121.46 (16)N3—C23—N4115.99 (12)
C2—C3—C7120.45 (16)S2—C23—N3122.89 (10)
C2—C3—C4118.07 (17)S2—C23—N4121.09 (10)
C3—C4—C5120.90 (18)N4—C24—C29119.94 (14)
C4—C5—C6120.69 (18)C25—C24—C29119.95 (14)
C1—C6—C5118.89 (18)N4—C24—C25120.04 (10)
N1—C8—N2116.15 (12)C24—C25—C26121.52 (13)
S1—C8—N2122.91 (10)C25—C26—C27118.0 (2)
S1—C8—N1120.93 (10)C25—C26—C30120.32 (18)
N2—C9—C14119.50 (14)C27—C26—C30121.7 (2)
N2—C9—C10119.76 (11)C26—C27—C28120.9 (3)
C10—C9—C14120.60 (12)C27—C28—C29121.2 (2)
C9—C10—C11120.50 (12)C24—C29—C28118.4 (2)
C10—C11—C15120.86 (18)C16—C17—H17120.00
C10—C11—C12118.09 (18)C18—C17—H17120.00
C12—C11—C15121.1 (2)C18—C19—H19119.00
C11—C12—C13121.5 (2)C20—C19—H19119.00
C12—C13—C14120.1 (2)C19—C20—H20120.00
C9—C14—C13119.25 (19)C21—C20—H20120.00
C1—C2—H2119.00C16—C21—H21121.00
C3—C2—H2119.00C20—C21—H21121.00
C5—C4—H4120.00C18—C22—H22A109.00
C3—C4—H4120.00C18—C22—H22B109.00
C4—C5—H5120.00C18—C22—H22C109.00
C6—C5—H5120.00C18—C22—H22D109.00
C5—C6—H6121.00C18—C22—H22E109.00
C1—C6—H6121.00C18—C22—H22F109.00
C3—C7—H7C109.00H22A—C22—H22B109.00
C3—C7—H7A109.00H22A—C22—H22C109.00
C3—C7—H7B109.00H22B—C22—H22C109.00
C3—C7—H7D109.00H22D—C22—H22E109.00
H7D—C7—H7F109.00H22D—C22—H22F109.00
C3—C7—H7E109.00H22E—C22—H22F109.00
H7D—C7—H7E109.00C24—C25—H25119.00
C3—C7—H7F109.00C26—C25—H25119.00
H7A—C7—H7B109.00C26—C27—H27119.00
H7A—C7—H7C109.00C28—C27—H27120.00
H7B—C7—H7C109.00C27—C28—H28119.00
H7E—C7—H7F109.00C29—C28—H28119.00
C11—C10—H10120.00C24—C29—H29121.00
C9—C10—H10120.00C28—C29—H29121.00
C11—C12—H12119.00C26—C30—H30A109.00
C13—C12—H12119.00C26—C30—H30B109.00
C14—C13—H13120.00C26—C30—H30C109.00
C12—C13—H13120.00H30A—C30—H30B109.00
C9—C14—H14120.00H30A—C30—H30C109.00
C13—C14—H14120.00H30B—C30—H30C109.00
C8—N1—C1—C259.6 (3)C10—C9—C14—C13−0.1 (3)
C8—N1—C1—C6−123.34 (19)N2—C9—C14—C13175.44 (18)
C1—N1—C8—S1−176.76 (14)C9—C10—C11—C15−178.34 (17)
C1—N1—C8—N24.4 (2)C9—C10—C11—C121.1 (3)
C9—N2—C8—S11.0 (2)C10—C11—C12—C13−0.6 (3)
C9—N2—C8—N1179.79 (14)C15—C11—C12—C13178.8 (2)
C8—N2—C9—C10−83.73 (19)C11—C12—C13—C14−0.2 (4)
C8—N2—C9—C14100.7 (2)C12—C13—C14—C90.5 (3)
C16—N3—C23—S2−6.7 (2)N3—C16—C17—C18177.07 (18)
C16—N3—C23—N4175.26 (16)C21—C16—C17—C18−0.1 (3)
C23—N3—C16—C17123.74 (19)N3—C16—C21—C20−176.69 (19)
C23—N3—C16—C21−59.1 (3)C17—C16—C21—C200.5 (3)
C23—N4—C24—C25−50.55 (19)C16—C17—C18—C19−0.4 (3)
C24—N4—C23—S2163.34 (11)C16—C17—C18—C22178.32 (18)
C24—N4—C23—N3−18.5 (2)C17—C18—C19—C200.6 (3)
C23—N4—C24—C29132.48 (17)C22—C18—C19—C20−178.1 (2)
N1—C1—C2—C3178.28 (17)C18—C19—C20—C21−0.2 (4)
C6—C1—C2—C31.2 (3)C19—C20—C21—C16−0.3 (3)
C2—C1—C6—C5−0.7 (3)N4—C24—C25—C26−178.66 (14)
N1—C1—C6—C5−177.76 (17)C29—C24—C25—C26−1.7 (2)
C1—C2—C3—C4−0.8 (3)N4—C24—C29—C28178.47 (17)
C1—C2—C3—C7−179.20 (17)C25—C24—C29—C281.5 (3)
C2—C3—C4—C5−0.1 (3)C24—C25—C26—C270.4 (3)
C7—C3—C4—C5178.25 (18)C24—C25—C26—C30179.50 (18)
C3—C4—C5—C60.6 (3)C25—C26—C27—C281.1 (3)
C4—C5—C6—C1−0.2 (3)C30—C26—C27—C28−178.0 (2)
N2—C9—C10—C11−176.23 (15)C26—C27—C28—C29−1.3 (4)
C14—C9—C10—C11−0.7 (2)C27—C28—C29—C240.0 (3)

Symmetry codes: (i) x+1, y, z−1; (ii) −x+2, −y, −z+1; (iii) −x+2, −y, −z; (iv) x−1, y, z+1; (v) −x+1, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) −x+2, −y+1, −z; (viii) x, y, z+1; (ix) x, y, z−1; (x) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···S2ii0.862.463.2528 (16)154
N4—H4A···S1ii0.862.633.4856 (16)172
C2—H2···S1iii0.932.833.7492 (19)168

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2714).

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