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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o735.
Published online 2010 March 3. doi:  10.1107/S160053681000721X
PMCID: PMC2983809

2-Amino-4-tert-butyl-5-(4-chloro­benz­yl)thia­zol-3-ium chloride

Abstract

The title compound, C14H18ClN2S+·Cl, crystallizes with two formula units in the asymmetric unit. The dihedral angles between the mean planes of the chloro­phenyl and thia­zole rings are 87.8 (2) and 88.0 (2)° in the two independent mol­ecules. In the crystal, the anions and cations are connected by N—H(...)Cl hydrogen bonds.

Related literature

For 2-amino-4-aryl­thia­zol compounds, see Marcantonio et al. (2002 [triangle]) and for their synthesis, see: Hu et al. (2007 [triangle]). For related structures, see: Cao et al. (2007 [triangle]); He et al. (2006 [triangle]); Hu et al. (2007 [triangle]); Xu et al. (2007 [triangle]).

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Object name is e-66-0o735-scheme1.jpg

Experimental

Crystal data

  • C14H18ClN2S+·Cl
  • M r = 317.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o735-efi1.jpg
  • a = 12.0810 (5) Å
  • b = 17.0208 (8) Å
  • c = 16.6465 (7) Å
  • β = 108.587 (1)°
  • V = 3244.4 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.52 mm−1
  • T = 173 K
  • 0.45 × 0.41 × 0.35 mm

Data collection

  • Bruker SMART 1000 CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.801, T max = 0.840
  • 16212 measured reflections
  • 7029 independent reflections
  • 5252 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.106
  • S = 1.03
  • 7029 reflections
  • 349 parameters
  • H-atom parameters constrained
  • Δρmax = 0.37 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT-Plus (Bruker, 2003 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681000721X/bt5189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000721X/bt5189Isup2.hkl

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

Acknowledgments

This work was funded by the Central University Basic Scientific Research Fund of Hunan University.

supplementary crystallographic information

Comment

Thiazole compounds are important nitrogen-containing heterocyclic compounds, because of their wide range of biological activity. 2-Amino-4-arylthiazol compounds play an important role in the field of organic pharmaceutical chemistry (Marcantonio et al., 2002). The synthesis of 2-amino-4-arylthiazoles was reported before (Cao et al., 2007, He et al., 2006, Hu et al., 2007 b, Xu et al., 2007). The title compound was prepared as part of an ongoing investigation on the synthesis and structural properties of 2-amino-4-arylthiazole derivatives.

Experimental

0.05 mol 2-Chloro-1-(4-chlorophenyl)-4,4-dimethyl-3-pentanone and 0.05 mol thiurea were dissolved in 100 ml EtOH and heated to reflux 12 h. After finishing the reaction, the solution was cooled and the precipitate formed was filtered out, dried, givingthe the title compound, yield 71.3 %. m.p.474–475.1 K.The crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperation.

Refinement

All H atoms were refined using a riding model, with N—H distances of 0.88 and C—H distances ranging from 0.95 to 0.98 Å, and with Uiso(H) = 1.2Ueq(C,N), or Uiso(H) = 1.5Ueq(Cmethyl).

Figures

Fig. 1.
The structure of the title compound showing 50% probability displacement ellipsoids.

Crystal data

C14H18ClN2S+·ClF(000) = 1328
Mr = 317.26Dx = 1.299 Mg m3
Monoclinic, P21/nMelting point: 474.5 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.0810 (5) ÅCell parameters from 7242 reflections
b = 17.0208 (8) Åθ = 2.2–27.0°
c = 16.6465 (7) ŵ = 0.52 mm1
β = 108.587 (1)°T = 173 K
V = 3244.4 (2) Å3Block, colorless
Z = 80.45 × 0.41 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer7029 independent reflections
Radiation source: fine-focus sealed tube5252 reflections with I > 2σ(I)
graphiteRint = 0.021
ω scansθmax = 27.1°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −15→15
Tmin = 0.801, Tmax = 0.840k = −21→6
16212 measured reflectionsl = −21→20

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0483P)2 + 1.4763P] where P = (Fo2 + 2Fc2)/3
7029 reflections(Δ/σ)max = 0.001
349 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.19 e Å3

Special details

Experimental. The 1H NMR (CDCl3,400 MHz) of 4-tert-butyl-5-(4-chlorobenzyl)thiazol-2-amine: δ (p.p.m.) 1.32(s, 9H, 3×CH3), 4.1(s, 2H, CH2),4.8(bs, 2H, NH2),7.12(d, J = 8.0 Hz, 2H, C6H4Cl 2,6-H),7.26(d, J = 8.0 Hz, 2H, C6H4Cl 3,5-H).
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

xyzUiso*/Ueq
Cl10.71220 (7)0.00215 (5)1.23595 (4)0.0741 (2)
Cl20.13936 (7)0.72411 (4)1.04620 (5)0.06191 (19)
Cl30.86628 (4)0.27452 (3)0.67478 (4)0.03947 (13)
Cl40.37086 (4)0.25787 (3)0.68564 (4)0.04414 (14)
S10.56742 (5)0.11936 (3)0.77844 (4)0.03767 (14)
S20.09432 (5)0.31590 (4)0.85845 (4)0.04243 (15)
C10.65841 (17)0.17991 (11)0.74588 (13)0.0335 (4)
C20.78072 (18)0.07566 (11)0.80669 (12)0.0307 (4)
C30.68127 (19)0.05130 (11)0.81964 (12)0.0334 (4)
C40.90343 (19)0.04129 (12)0.83044 (13)0.0378 (5)
C50.9824 (2)0.08743 (17)0.90556 (16)0.0584 (7)
H5A0.98630.14230.88900.088*
H5B1.06100.06460.92310.088*
H5C0.95070.08500.95280.088*
C60.9041 (3)−0.04586 (15)0.85414 (19)0.0631 (7)
H6A0.8763−0.05150.90310.095*
H6B0.9837−0.06650.86840.095*
H6C0.8526−0.07520.80600.095*
C70.9498 (2)0.04806 (17)0.75503 (16)0.0545 (7)
H7A0.89650.02090.70590.082*
H7B1.02740.02400.76980.082*
H7C0.95510.10360.74120.082*
C80.6485 (2)−0.01887 (12)0.86164 (13)0.0396 (5)
H8A0.6930−0.06480.85210.048*
H8B0.5645−0.03000.83350.048*
C90.66972 (19)−0.01103 (12)0.95659 (13)0.0346 (4)
C100.6492 (2)−0.07585 (14)0.99990 (15)0.0546 (7)
H100.6256−0.12390.97030.065*
C110.6625 (3)−0.07207 (16)1.08559 (15)0.0636 (8)
H110.6478−0.11701.11460.076*
C120.6971 (2)−0.00275 (15)1.12798 (14)0.0470 (6)
C130.7210 (2)0.06203 (14)1.08781 (14)0.0484 (6)
H130.74670.10941.11820.058*
C140.7073 (2)0.05744 (13)1.00207 (14)0.0452 (5)
H140.72400.10220.97390.054*
C150.17384 (17)0.28756 (13)0.79473 (14)0.0391 (5)
C160.31809 (17)0.33017 (11)0.91593 (13)0.0318 (4)
C170.22313 (18)0.34283 (12)0.93980 (13)0.0348 (4)
C180.44803 (17)0.34477 (12)0.95687 (13)0.0331 (4)
C190.4745 (2)0.38497 (14)1.04315 (14)0.0473 (6)
H19A0.43000.43401.03660.071*
H19B0.55820.39661.06580.071*
H19C0.45230.35011.08230.071*
C200.51412 (19)0.26639 (13)0.96966 (16)0.0462 (5)
H20A0.48730.23271.00750.069*
H20B0.59800.27620.99480.069*
H20C0.49920.24020.91480.069*
C210.4904 (2)0.39763 (14)0.89765 (14)0.0453 (5)
H21A0.48100.36990.84430.068*
H21B0.57290.41060.92480.068*
H21C0.44410.44610.88610.068*
C220.2038 (2)0.37428 (12)1.01857 (13)0.0383 (5)
H22A0.27250.36051.06770.046*
H22B0.13540.34701.02610.046*
C230.18367 (16)0.46231 (12)1.02080 (12)0.0314 (4)
C240.15976 (19)0.49386 (13)1.09061 (13)0.0409 (5)
H240.15270.45961.13370.049*
C250.1460 (2)0.57353 (14)1.09893 (14)0.0449 (5)
H250.13120.59401.14760.054*
C260.15426 (18)0.62310 (12)1.03541 (14)0.0388 (5)
C270.17377 (19)0.59376 (13)0.96404 (13)0.0395 (5)
H270.17660.62810.91970.047*
C280.18928 (19)0.51355 (12)0.95759 (13)0.0374 (5)
H280.20410.49330.90880.045*
N10.76480 (14)0.14883 (9)0.76544 (10)0.0305 (4)
H10.82200.17280.75320.037*
N20.62892 (16)0.24695 (11)0.70590 (14)0.0518 (5)
H2A0.68080.27400.69050.062*
H2B0.55720.26490.69450.062*
N30.28711 (14)0.29818 (10)0.83386 (11)0.0340 (4)
H30.33990.28590.80980.041*
N40.13062 (16)0.25857 (13)0.71759 (13)0.0569 (6)
H4A0.17770.24500.68910.068*
H4B0.05470.25280.69460.068*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0859 (5)0.1070 (6)0.0370 (3)−0.0352 (4)0.0301 (3)−0.0158 (3)
Cl20.0842 (5)0.0404 (3)0.0755 (5)0.0100 (3)0.0456 (4)−0.0052 (3)
Cl30.0308 (3)0.0335 (3)0.0563 (3)−0.0032 (2)0.0168 (2)0.0068 (2)
Cl40.0338 (3)0.0539 (3)0.0475 (3)0.0088 (2)0.0170 (2)−0.0081 (2)
S10.0384 (3)0.0332 (3)0.0488 (3)−0.0005 (2)0.0242 (2)0.0046 (2)
S20.0306 (3)0.0534 (3)0.0479 (3)−0.0055 (2)0.0191 (2)−0.0129 (3)
C10.0339 (11)0.0289 (10)0.0426 (12)0.0028 (8)0.0191 (9)0.0053 (8)
C20.0418 (11)0.0245 (9)0.0255 (10)0.0034 (8)0.0102 (8)−0.0001 (7)
C30.0459 (12)0.0245 (9)0.0315 (10)0.0014 (8)0.0147 (9)0.0005 (8)
C40.0428 (12)0.0316 (11)0.0364 (11)0.0107 (9)0.0090 (9)0.0027 (9)
C50.0449 (14)0.0663 (17)0.0520 (15)0.0113 (12)−0.0015 (12)−0.0127 (13)
C60.0666 (17)0.0408 (14)0.0777 (19)0.0192 (13)0.0172 (15)0.0162 (13)
C70.0453 (13)0.0696 (17)0.0521 (15)0.0258 (13)0.0205 (11)0.0077 (13)
C80.0595 (14)0.0280 (10)0.0332 (11)−0.0068 (9)0.0172 (10)0.0009 (8)
C90.0425 (12)0.0307 (10)0.0338 (11)−0.0053 (9)0.0164 (9)−0.0002 (8)
C100.0857 (19)0.0417 (13)0.0420 (13)−0.0294 (13)0.0284 (13)−0.0065 (10)
C110.100 (2)0.0567 (16)0.0399 (14)−0.0356 (15)0.0311 (14)−0.0010 (12)
C120.0496 (13)0.0640 (15)0.0326 (12)−0.0179 (12)0.0206 (10)−0.0089 (10)
C130.0587 (15)0.0484 (13)0.0407 (13)−0.0160 (12)0.0195 (11)−0.0134 (10)
C140.0623 (15)0.0334 (11)0.0447 (13)−0.0125 (10)0.0240 (11)−0.0034 (10)
C150.0281 (10)0.0450 (12)0.0471 (13)−0.0062 (9)0.0159 (9)−0.0145 (10)
C160.0342 (10)0.0256 (9)0.0361 (11)−0.0035 (8)0.0117 (9)−0.0034 (8)
C170.0374 (11)0.0328 (10)0.0358 (11)−0.0027 (9)0.0139 (9)−0.0025 (8)
C180.0331 (10)0.0292 (10)0.0342 (11)−0.0053 (8)0.0067 (8)−0.0019 (8)
C190.0455 (13)0.0499 (14)0.0411 (13)−0.0052 (11)0.0064 (10)−0.0121 (10)
C200.0384 (12)0.0364 (12)0.0591 (15)0.0005 (9)0.0089 (11)−0.0026 (10)
C210.0401 (12)0.0470 (13)0.0447 (13)−0.0166 (10)0.0078 (10)0.0030 (10)
C220.0460 (12)0.0386 (11)0.0354 (11)0.0022 (9)0.0199 (10)0.0022 (9)
C230.0270 (10)0.0395 (11)0.0275 (10)0.0039 (8)0.0085 (8)0.0000 (8)
C240.0469 (13)0.0484 (13)0.0327 (11)0.0143 (10)0.0203 (10)0.0085 (9)
C250.0519 (14)0.0530 (14)0.0365 (12)0.0184 (11)0.0236 (10)0.0014 (10)
C260.0368 (11)0.0366 (11)0.0452 (12)0.0068 (9)0.0161 (10)−0.0027 (9)
C270.0449 (12)0.0402 (12)0.0376 (12)0.0008 (10)0.0191 (10)0.0037 (9)
C280.0480 (13)0.0402 (11)0.0274 (10)−0.0005 (9)0.0169 (9)−0.0030 (8)
N10.0308 (8)0.0263 (8)0.0377 (9)0.0031 (7)0.0154 (7)0.0052 (7)
N20.0365 (10)0.0377 (10)0.0897 (16)0.0130 (8)0.0322 (10)0.0280 (10)
N30.0271 (8)0.0378 (9)0.0394 (10)−0.0060 (7)0.0135 (7)−0.0120 (7)
N40.0279 (9)0.0891 (16)0.0538 (12)−0.0124 (10)0.0129 (9)−0.0382 (12)

Geometric parameters (Å, °)

Cl1—C121.750 (2)C15—N41.318 (3)
Cl2—C261.744 (2)C15—N31.327 (3)
S1—C11.716 (2)C16—C171.346 (3)
S1—C31.762 (2)C16—N31.406 (2)
S2—C151.712 (2)C16—C181.519 (3)
S2—C171.767 (2)C17—C221.502 (3)
C1—N21.312 (3)C18—C191.530 (3)
C1—N11.331 (2)C18—C201.534 (3)
C2—C31.352 (3)C18—C211.537 (3)
C2—N11.406 (2)C19—H19A0.9800
C2—C41.524 (3)C19—H19B0.9800
C3—C81.500 (3)C19—H19C0.9800
C4—C51.527 (3)C20—H20A0.9800
C4—C71.533 (3)C20—H20B0.9800
C4—C61.534 (3)C20—H20C0.9800
C5—H5A0.9800C21—H21A0.9800
C5—H5B0.9800C21—H21B0.9800
C5—H5C0.9800C21—H21C0.9800
C6—H6A0.9800C22—C231.520 (3)
C6—H6B0.9800C22—H22A0.9900
C6—H6C0.9800C22—H22B0.9900
C7—H7A0.9800C23—C281.385 (3)
C7—H7B0.9800C23—C241.392 (3)
C7—H7C0.9800C24—C251.378 (3)
C8—C91.524 (3)C24—H240.9500
C8—H8A0.9900C25—C261.381 (3)
C8—H8B0.9900C25—H250.9500
C9—C101.383 (3)C26—C271.377 (3)
C9—C141.385 (3)C27—C281.387 (3)
C10—C111.385 (3)C27—H270.9500
C10—H100.9500C28—H280.9500
C11—C121.370 (3)N1—H10.8800
C11—H110.9500N2—H2A0.8800
C12—C131.368 (3)N2—H2B0.8800
C13—C141.385 (3)N3—H30.8800
C13—H130.9500N4—H4A0.8800
C14—H140.9500N4—H4B0.8800
C1—S1—C391.06 (10)N3—C16—C18114.59 (17)
C15—S2—C1790.97 (10)C16—C17—C22134.4 (2)
N2—C1—N1123.71 (18)C16—C17—S2110.96 (15)
N2—C1—S1125.80 (16)C22—C17—S2114.66 (15)
N1—C1—S1110.49 (14)C16—C18—C19111.79 (17)
C3—C2—N1111.08 (17)C16—C18—C20109.72 (16)
C3—C2—C4132.96 (18)C19—C18—C20108.34 (18)
N1—C2—C4115.92 (17)C16—C18—C21108.38 (16)
C2—C3—C8134.36 (19)C19—C18—C21109.12 (17)
C2—C3—S1111.08 (14)C20—C18—C21109.46 (18)
C8—C3—S1114.55 (16)C18—C19—H19A109.5
C2—C4—C5108.51 (17)C18—C19—H19B109.5
C2—C4—C7109.74 (16)H19A—C19—H19B109.5
C5—C4—C7109.6 (2)C18—C19—H19C109.5
C2—C4—C6111.26 (19)H19A—C19—H19C109.5
C5—C4—C6109.6 (2)H19B—C19—H19C109.5
C7—C4—C6108.1 (2)C18—C20—H20A109.5
C4—C5—H5A109.5C18—C20—H20B109.5
C4—C5—H5B109.5H20A—C20—H20B109.5
H5A—C5—H5B109.5C18—C20—H20C109.5
C4—C5—H5C109.5H20A—C20—H20C109.5
H5A—C5—H5C109.5H20B—C20—H20C109.5
H5B—C5—H5C109.5C18—C21—H21A109.5
C4—C6—H6A109.5C18—C21—H21B109.5
C4—C6—H6B109.5H21A—C21—H21B109.5
H6A—C6—H6B109.5C18—C21—H21C109.5
C4—C6—H6C109.5H21A—C21—H21C109.5
H6A—C6—H6C109.5H21B—C21—H21C109.5
H6B—C6—H6C109.5C17—C22—C23116.30 (17)
C4—C7—H7A109.5C17—C22—H22A108.2
C4—C7—H7B109.5C23—C22—H22A108.2
H7A—C7—H7B109.5C17—C22—H22B108.2
C4—C7—H7C109.5C23—C22—H22B108.2
H7A—C7—H7C109.5H22A—C22—H22B107.4
H7B—C7—H7C109.5C28—C23—C24117.70 (19)
C3—C8—C9115.56 (17)C28—C23—C22123.74 (18)
C3—C8—H8A108.4C24—C23—C22118.56 (18)
C9—C8—H8A108.4C25—C24—C23121.8 (2)
C3—C8—H8B108.4C25—C24—H24119.1
C9—C8—H8B108.4C23—C24—H24119.1
H8A—C8—H8B107.5C24—C25—C26118.94 (19)
C10—C9—C14117.9 (2)C24—C25—H25120.5
C10—C9—C8118.15 (18)C26—C25—H25120.5
C14—C9—C8123.92 (18)C27—C26—C25120.9 (2)
C9—C10—C11121.2 (2)C27—C26—Cl2119.87 (17)
C9—C10—H10119.4C25—C26—Cl2119.25 (16)
C11—C10—H10119.4C26—C27—C28119.2 (2)
C12—C11—C10119.1 (2)C26—C27—H27120.4
C12—C11—H11120.4C28—C27—H27120.4
C10—C11—H11120.4C23—C28—C27121.38 (19)
C13—C12—C11121.3 (2)C23—C28—H28119.3
C13—C12—Cl1119.65 (18)C27—C28—H28119.3
C11—C12—Cl1119.02 (19)C1—N1—C2116.29 (16)
C12—C13—C14118.9 (2)C1—N1—H1121.9
C12—C13—H13120.5C2—N1—H1121.9
C14—C13—H13120.5C1—N2—H2A120.0
C9—C14—C13121.4 (2)C1—N2—H2B120.0
C9—C14—H14119.3H2A—N2—H2B120.0
C13—C14—H14119.3C15—N3—C16116.31 (17)
N4—C15—N3123.75 (19)C15—N3—H3121.8
N4—C15—S2125.65 (16)C16—N3—H3121.8
N3—C15—S2110.60 (15)C15—N4—H4A120.0
C17—C16—N3111.16 (17)C15—N4—H4B120.0
C17—C16—C18134.23 (18)H4A—N4—H4B120.0
C3—S1—C1—N2179.1 (2)N3—C16—C17—S2−0.9 (2)
C3—S1—C1—N10.27 (16)C18—C16—C17—S2177.18 (19)
N1—C2—C3—C8−177.9 (2)C15—S2—C17—C160.42 (17)
C4—C2—C3—C8−0.4 (4)C15—S2—C17—C22−179.73 (17)
N1—C2—C3—S11.0 (2)C17—C16—C18—C19−2.1 (3)
C4—C2—C3—S1178.50 (18)N3—C16—C18—C19175.88 (18)
C1—S1—C3—C2−0.75 (16)C17—C16—C18—C20118.1 (3)
C1—S1—C3—C8178.39 (16)N3—C16—C18—C20−63.9 (2)
C3—C2—C4—C5−103.9 (3)C17—C16—C18—C21−122.4 (3)
N1—C2—C4—C573.5 (2)N3—C16—C18—C2155.6 (2)
C3—C2—C4—C7136.4 (2)C16—C17—C22—C2391.1 (3)
N1—C2—C4—C7−46.2 (2)S2—C17—C22—C23−88.7 (2)
C3—C2—C4—C616.8 (3)C17—C22—C23—C28−3.9 (3)
N1—C2—C4—C6−165.77 (19)C17—C22—C23—C24176.98 (19)
C2—C3—C8—C987.5 (3)C28—C23—C24—C25−2.3 (3)
S1—C3—C8—C9−91.4 (2)C22—C23—C24—C25176.9 (2)
C3—C8—C9—C10−175.3 (2)C23—C24—C25—C261.2 (4)
C3—C8—C9—C145.3 (3)C24—C25—C26—C271.1 (3)
C14—C9—C10—C111.8 (4)C24—C25—C26—Cl2−178.98 (18)
C8—C9—C10—C11−177.6 (3)C25—C26—C27—C28−2.2 (3)
C9—C10—C11—C12−0.3 (5)Cl2—C26—C27—C28177.89 (17)
C10—C11—C12—C13−1.4 (5)C24—C23—C28—C271.1 (3)
C10—C11—C12—Cl1179.3 (2)C22—C23—C28—C27−178.0 (2)
C11—C12—C13—C141.5 (4)C26—C27—C28—C231.1 (3)
Cl1—C12—C13—C14−179.3 (2)N2—C1—N1—C2−178.6 (2)
C10—C9—C14—C13−1.8 (4)S1—C1—N1—C20.3 (2)
C8—C9—C14—C13177.6 (2)C3—C2—N1—C1−0.9 (2)
C12—C13—C14—C90.2 (4)C4—C2—N1—C1−178.81 (17)
C17—S2—C15—N4179.8 (2)N4—C15—N3—C16179.7 (2)
C17—S2—C15—N30.19 (17)S2—C15—N3—C16−0.8 (2)
N3—C16—C17—C22179.3 (2)C17—C16—N3—C151.1 (3)
C18—C16—C17—C22−2.6 (4)C18—C16—N3—C15−177.38 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···Cl30.882.333.0882 (16)144
N2—H2A···Cl30.882.343.1078 (19)146
N2—H2B···Cl40.882.213.0327 (19)155
N3—H3···Cl40.882.273.0289 (17)145
N4—H4A···Cl40.882.363.1131 (19)143
N4—H4B···Cl3i0.882.223.0543 (19)157

Symmetry codes: (i) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5189).

References

  • Bruker (2001). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2003). SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cao, G., Hu, A.-X., Xu, J.-J. & Xia, L. (2007). Acta Cryst. E63, o2534.
  • He, D.-H., Cao, G. & Hu, A.-X. (2006). Acta Cryst. E62, o5637–o5638.
  • Hu, A.-X., Zhang, J.-Y., Cao, G., Xu, J.-J. & Xia, L. (2007). Acta Cryst. E63, o2533.
  • Marcantonio, K. M., Frey, L. F., Murry, J. A. & Chen, C. Y. (2002). Tetrahedron Lett. 43, 8845–8848.
  • Sheldrick, G. M. (2004). SADABS University of Gottingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xu, J.-J., Hu, A.-X. & Cao, G. (2007). Acta Cryst. E63, o533–o534.

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