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Two independent mol­ecules of the title compound, C18H13ClN2S, exibit a noticeable difference in the conformation of the cyclo­hexa­diene fragment, which shows much more pro­nounced deviations from planarity in one of the mol­ecules than in the other.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014787/ya6057sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014787/ya6057Isup2.hkl
Contains datablock I

CCDC reference: 175357

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.042
  • wR factor = 0.102
  • Data-to-parameter ratio = 15.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.40 From the CIF: _reflns_number_total 6309 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 6648 Completeness (_total/calc) 94.90% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Benzothiazole and its fused derivatives have shown a wide range of remarkable activities, viz. fungicidal, analgesic, anti-inflammatory, anticonvulsant, anaesthetic and pesticide (Di Braccio et al., 1986; Evans, 1974; Baetz, 1973; Mehra et al., 1980; Bartovic et al., 1995; Khan & Rastogi, 1991).

We have used different 2-aminobenzothiazole derivatives with Mannich bases to prepare similar fused derivatives (Quiroga et al., 1992, 1994, 1999; Quiroga, Insuasty, Hernández et al., 1998; Quiroga, Insuasty, Cruz et al., 1998).

Here we report the crystal structure of 11-chloro-6H-5,7-dihydrobenzothiazolo[2,3-b]benzo[h]quinazoline, (I), prepared by reaction of 2-amino-6-chlorobenzothiazole with 2-dimethylaminomethylenetetralone hydrochloride. Two independent molecules (Fig. 1) in the asymmetric unit of (I) differ in the degree of non-planarity of the cyclohexadiene rings (C10A—C16B—C16A—C12A—C112—C111 and C21A—C26B—C26A—C22A—C212—C211 in molecules A and B, respectively). As one can see from the torsion angles (Table 1), the deviations from planarity in molecule A are much more pronounced than in molecule B.

Experimental top

A solution of 2-amino-6-chlorobenzothiazole (0.5 mmol) and 2-dimethylaminomethylenetetralone hydrochloride (1 mmol) in absolute ethanol (15 ml) was heated to reflux for 30 min. The title compound was isolated by cooling, followed by filtration, washing with ethanol, drying and recrystallization from ethanol. The compound was obtained as yellow crystals; m.p 452 K, yield 70%.

Refinement top

H atoms were taken into account in the riding-motion approximation with Uiso equal to 1.2Ueq of the corresonding carrier atom.

Computing details top

Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. View of molecule A of (I) showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are drawn as circles of arbitrary radii.
[Figure 2] Fig. 2. View of molecule B of (I) showing the numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms are drawn as circles of arbitrary radii.
11-Chloro-5H-6,7-dihydrobenzothiazolo[2,3-b]benzo[h]quinazoline top
Crystal data top
C18H13ClN2SF(000) = 672
Mr = 324.82Dx = 1.478 Mg m3
Triclinic, P1Melting point: 452 K
a = 7.2637 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.4294 (5) ÅCell parameters from 20568 reflections
c = 15.1081 (5) Åθ = 2.9–27.5°
α = 70.368 (3)°µ = 0.40 mm1
β = 78.550 (2)°T = 120 K
γ = 89.0800 (14)°Block, orange
V = 1459.56 (9) Å30.20 × 0.10 × 0.10 mm
Z = 4
Data collection top
Kappa-CCD
diffractometer
6309 independent reflections
Radiation source: fine-focus sealed X-ray tube4470 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.060
ϕ scans, and ω scans with κ offsetsθmax = 27.4°, θmin = 2.9°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 99
Tmin = 0.924, Tmax = 0.961k = 1818
20548 measured reflectionsl = 1819
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0481P)2 + 0.0093P]
where P = (Fo2 + 2Fc2)/3
6309 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.38 e Å3
Crystal data top
C18H13ClN2Sγ = 89.0800 (14)°
Mr = 324.82V = 1459.56 (9) Å3
Triclinic, P1Z = 4
a = 7.2637 (3) ÅMo Kα radiation
b = 14.4294 (5) ŵ = 0.40 mm1
c = 15.1081 (5) ÅT = 120 K
α = 70.368 (3)°0.20 × 0.10 × 0.10 mm
β = 78.550 (2)°
Data collection top
Kappa-CCD
diffractometer
6309 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
4470 reflections with I > 2σ(I)
Tmin = 0.924, Tmax = 0.961Rint = 0.060
20548 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 1.03Δρmax = 0.32 e Å3
6309 reflectionsΔρmin = 0.38 e Å3
397 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C110.9497 (3)0.13006 (13)0.66763 (12)0.0210 (4)
C120.8722 (3)0.12940 (13)0.75932 (13)0.0235 (4)
C130.6797 (3)0.13427 (14)0.78764 (12)0.0241 (4)
Cl130.58735 (8)0.13428 (4)0.90268 (3)0.03721 (16)
C140.5574 (3)0.13836 (13)0.72597 (12)0.0224 (4)
C14A0.6350 (3)0.13698 (13)0.63522 (12)0.0197 (4)
C41A0.8302 (3)0.13335 (12)0.60551 (12)0.0187 (4)
S150.51835 (7)0.13400 (4)0.54521 (3)0.02312 (13)
C15A0.7328 (3)0.12633 (13)0.46944 (12)0.0184 (4)
N160.7403 (2)0.11994 (10)0.38638 (10)0.0183 (3)
C16A0.9261 (3)0.11903 (12)0.33377 (12)0.0185 (4)
C16B0.9379 (3)0.10865 (13)0.23924 (12)0.0186 (4)
C170.7835 (3)0.07523 (13)0.21374 (12)0.0222 (4)
C180.7983 (3)0.06674 (13)0.12385 (13)0.0258 (5)
C190.9677 (3)0.09275 (14)0.05758 (13)0.0267 (5)
C1101.1225 (3)0.12491 (14)0.08292 (13)0.0259 (5)
C10A1.1115 (3)0.13234 (13)0.17268 (13)0.0205 (4)
C1111.2770 (3)0.16999 (14)0.20051 (12)0.0241 (4)
C1121.2746 (3)0.12503 (14)0.30755 (13)0.0220 (4)
C1131.0762 (3)0.13229 (13)0.46404 (12)0.0202 (4)
C12A1.0824 (2)0.12598 (12)0.36654 (12)0.0178 (4)
N1140.8801 (2)0.12882 (10)0.51403 (10)0.0172 (3)
C210.0308 (3)0.34448 (13)0.15182 (13)0.0256 (5)
C220.0452 (3)0.34242 (13)0.24258 (13)0.0277 (5)
C230.2377 (3)0.35663 (14)0.27785 (13)0.0278 (5)
Cl230.32929 (8)0.35263 (4)0.39189 (3)0.03944 (16)
C240.3596 (3)0.37532 (13)0.22472 (12)0.0262 (5)
C24A0.2820 (3)0.38067 (13)0.13546 (12)0.0226 (4)
C42A0.0888 (3)0.36402 (13)0.09826 (12)0.0203 (4)
S250.39665 (7)0.40991 (4)0.05581 (3)0.02585 (14)
C25A0.1820 (3)0.39806 (13)0.02719 (12)0.0188 (4)
N260.1730 (2)0.41199 (10)0.10724 (10)0.0192 (3)
C26A0.0081 (3)0.39046 (12)0.16931 (12)0.0172 (4)
C26B0.0152 (3)0.39420 (13)0.26629 (12)0.0179 (4)
C270.1472 (3)0.41247 (13)0.29521 (12)0.0219 (4)
C280.1393 (3)0.41513 (14)0.38667 (13)0.0257 (4)
C290.0317 (3)0.39838 (14)0.45139 (13)0.0261 (5)
C2100.1935 (3)0.37956 (13)0.42335 (13)0.0240 (4)
C21A0.1887 (3)0.37777 (13)0.33173 (12)0.0192 (4)
C2110.3683 (3)0.36587 (14)0.29940 (12)0.0223 (4)
C2120.3439 (3)0.32751 (13)0.21578 (12)0.0215 (4)
C2130.1543 (3)0.35037 (13)0.04946 (12)0.0201 (4)
C22A0.1606 (3)0.36143 (12)0.14533 (12)0.0176 (4)
N2140.0372 (2)0.37192 (11)0.00789 (10)0.0188 (3)
H111.08180.12830.64760.025*
H120.95170.12560.80320.028*
H140.42570.14200.74570.027*
H170.66690.05810.25850.027*
H180.69280.04320.10760.031*
H190.97770.08860.00460.032*
H1101.23830.14210.03760.031*
H11A1.27510.24250.18250.029*
H11B1.39530.15450.16410.029*
H11C1.31330.05630.32240.026*
H11D1.36620.16260.32470.026*
H11E1.14150.07670.50170.024*
H11F1.14190.19450.45760.024*
H210.16220.33280.12660.031*
H220.03500.33120.28100.033*
H240.49150.38410.24900.031*
H270.26500.42330.25150.026*
H280.25100.42840.40510.031*
H290.03780.39980.51430.031*
H2100.31030.36760.46790.029*
H21A0.42550.43050.28080.027*
H21B0.45760.32010.35450.027*
H21C0.35270.25460.24130.026*
H21D0.44830.34930.18160.026*
H21E0.19670.28230.05880.024*
H21F0.24040.39610.01520.024*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0210 (11)0.0209 (10)0.0218 (10)0.0010 (8)0.0068 (8)0.0069 (8)
C120.0275 (12)0.0232 (11)0.0211 (10)0.0005 (9)0.0088 (8)0.0068 (8)
C130.0300 (12)0.0251 (11)0.0166 (10)0.0022 (9)0.0049 (8)0.0064 (8)
Cl130.0376 (3)0.0555 (4)0.0200 (3)0.0023 (3)0.0037 (2)0.0159 (2)
C140.0198 (11)0.0237 (11)0.0218 (10)0.0021 (8)0.0016 (8)0.0067 (8)
C14A0.0188 (11)0.0203 (10)0.0199 (10)0.0016 (8)0.0060 (8)0.0054 (8)
C41A0.0205 (11)0.0156 (10)0.0191 (10)0.0003 (8)0.0031 (8)0.0053 (7)
S150.0153 (3)0.0354 (3)0.0206 (3)0.0030 (2)0.00396 (19)0.0118 (2)
C15A0.0151 (10)0.0192 (10)0.0203 (10)0.0006 (8)0.0044 (7)0.0054 (7)
N160.0153 (9)0.0237 (9)0.0161 (8)0.0023 (7)0.0022 (6)0.0076 (6)
C16A0.0171 (10)0.0156 (10)0.0202 (10)0.0008 (7)0.0011 (8)0.0043 (7)
C16B0.0192 (10)0.0166 (10)0.0199 (10)0.0048 (8)0.0047 (8)0.0058 (7)
C170.0219 (11)0.0234 (11)0.0220 (10)0.0019 (8)0.0047 (8)0.0085 (8)
C180.0301 (12)0.0250 (11)0.0267 (11)0.0023 (9)0.0105 (9)0.0119 (8)
C190.0360 (13)0.0259 (11)0.0202 (10)0.0060 (9)0.0054 (9)0.0108 (8)
C1100.0259 (12)0.0264 (11)0.0239 (11)0.0043 (9)0.0000 (8)0.0095 (8)
C10A0.0209 (11)0.0164 (10)0.0220 (10)0.0048 (8)0.0028 (8)0.0049 (7)
C1110.0186 (11)0.0245 (11)0.0246 (11)0.0004 (8)0.0011 (8)0.0053 (8)
C1120.0166 (10)0.0213 (10)0.0265 (10)0.0004 (8)0.0027 (8)0.0069 (8)
C1130.0149 (10)0.0215 (10)0.0239 (10)0.0009 (8)0.0039 (8)0.0075 (8)
C12A0.0156 (10)0.0171 (10)0.0196 (10)0.0004 (8)0.0025 (8)0.0052 (7)
N1140.0133 (8)0.0221 (9)0.0176 (8)0.0022 (6)0.0047 (6)0.0075 (6)
C210.0315 (12)0.0238 (11)0.0223 (11)0.0005 (9)0.0069 (9)0.0080 (8)
C220.0389 (14)0.0232 (11)0.0243 (11)0.0031 (9)0.0118 (9)0.0095 (8)
C230.0428 (14)0.0241 (11)0.0176 (10)0.0100 (9)0.0077 (9)0.0080 (8)
Cl230.0512 (4)0.0497 (4)0.0218 (3)0.0189 (3)0.0085 (2)0.0179 (2)
C240.0264 (12)0.0297 (12)0.0202 (11)0.0083 (9)0.0014 (8)0.0077 (8)
C24A0.0236 (11)0.0234 (11)0.0214 (10)0.0056 (8)0.0068 (8)0.0073 (8)
C42A0.0260 (12)0.0169 (10)0.0173 (10)0.0022 (8)0.0036 (8)0.0053 (7)
S250.0174 (3)0.0404 (3)0.0201 (3)0.0031 (2)0.0030 (2)0.0114 (2)
C25A0.0168 (10)0.0189 (10)0.0197 (10)0.0014 (8)0.0042 (8)0.0053 (7)
N260.0172 (9)0.0238 (9)0.0157 (8)0.0001 (7)0.0016 (6)0.0063 (6)
C26A0.0162 (10)0.0148 (9)0.0192 (10)0.0023 (7)0.0037 (8)0.0040 (7)
C26B0.0192 (11)0.0168 (10)0.0171 (9)0.0024 (8)0.0043 (7)0.0050 (7)
C270.0180 (11)0.0260 (11)0.0223 (10)0.0020 (8)0.0049 (8)0.0086 (8)
C280.0247 (11)0.0316 (12)0.0262 (11)0.0043 (9)0.0111 (9)0.0138 (9)
C290.0320 (13)0.0297 (11)0.0187 (10)0.0039 (9)0.0047 (9)0.0115 (8)
C2100.0231 (11)0.0267 (11)0.0208 (10)0.0004 (9)0.0001 (8)0.0085 (8)
C21A0.0197 (11)0.0157 (10)0.0208 (10)0.0001 (8)0.0017 (8)0.0056 (7)
C2110.0157 (10)0.0250 (11)0.0233 (10)0.0019 (8)0.0001 (8)0.0067 (8)
C2120.0162 (10)0.0243 (11)0.0218 (10)0.0017 (8)0.0036 (8)0.0050 (8)
C2130.0154 (10)0.0226 (10)0.0227 (10)0.0017 (8)0.0034 (8)0.0084 (8)
C22A0.0179 (10)0.0167 (10)0.0173 (9)0.0019 (8)0.0040 (7)0.0046 (7)
N2140.0161 (9)0.0237 (9)0.0170 (8)0.0004 (7)0.0023 (6)0.0082 (6)
Geometric parameters (Å, º) top
C11—C121.385 (3)C21—C221.383 (3)
C11—C41A1.389 (2)C21—C42A1.389 (3)
C11—H110.9500C21—H210.9500
C12—C131.386 (3)C22—C231.386 (3)
C12—H120.9500C22—H220.9500
C13—C141.397 (3)C23—C241.391 (3)
C13—Cl131.7345 (18)C23—Cl231.7391 (18)
C14—C14A1.382 (2)C24—C24A1.382 (2)
C14—H140.9500C24—H240.9500
C14A—C41A1.405 (3)C24A—C42A1.397 (3)
C14A—S151.7515 (18)C24A—S251.7519 (18)
C41A—N1141.381 (2)C42A—N2141.385 (2)
S15—C15A1.7667 (18)S25—C25A1.7667 (18)
C15A—N161.279 (2)C25A—N261.280 (2)
C15A—N1141.379 (2)C25A—N2141.377 (2)
N16—C16A1.426 (2)N26—C26A1.426 (2)
C16A—C12A1.343 (2)C26A—C22A1.346 (2)
C16A—C16B1.471 (2)C26A—C26B1.475 (2)
C16B—C171.397 (3)C26B—C271.394 (2)
C16B—C10A1.414 (2)C26B—C21A1.407 (2)
C17—C181.387 (2)C27—C281.385 (2)
C17—H170.9500C27—H270.9500
C18—C191.389 (3)C28—C291.388 (3)
C18—H180.9500C28—H280.9500
C19—C1101.390 (3)C29—C2101.386 (3)
C19—H190.9500C29—H290.9500
C110—C10A1.383 (2)C210—C21A1.387 (2)
C110—H1100.9500C210—H2100.9500
C10A—C1111.514 (3)C21A—C2111.512 (3)
C111—C1121.523 (2)C211—C2121.520 (2)
C111—H11A0.9900C211—H21A0.9900
C111—H11B0.9900C211—H21B0.9900
C112—C12A1.502 (2)C212—C22A1.501 (2)
C112—H11C0.9900C212—H21C0.9900
C112—H11D0.9900C212—H21D0.9900
C113—N1141.467 (2)C213—N2141.462 (2)
C113—C12A1.498 (2)C213—C22A1.501 (2)
C113—H11E0.9900C213—H21E0.9900
C113—H11F0.9900C213—H21F0.9900
C12—C11—C41A118.63 (18)C22—C21—C42A118.71 (19)
C12—C11—H11120.7C22—C21—H21120.6
C41A—C11—H11120.7C42A—C21—H21120.6
C11—C12—C13120.60 (18)C21—C22—C23120.38 (18)
C11—C12—H12119.7C21—C22—H22119.8
C13—C12—H12119.7C23—C22—H22119.8
C12—C13—C14121.61 (17)C22—C23—C24121.59 (18)
C12—C13—Cl13119.46 (14)C22—C23—Cl23119.31 (15)
C14—C13—Cl13118.93 (15)C24—C23—Cl23119.09 (16)
C14A—C14—C13117.56 (18)C24A—C24—C23117.71 (19)
C14A—C14—H14121.2C24A—C24—H24121.1
C13—C14—H14121.2C23—C24—H24121.1
C14—C14A—C41A121.20 (17)C24—C24A—C42A121.11 (17)
C14—C14A—S15128.15 (15)C24—C24A—S25128.13 (16)
C41A—C14A—S15110.59 (13)C42A—C24A—S25110.74 (13)
N114—C41A—C11126.85 (17)N214—C42A—C21126.64 (18)
N114—C41A—C14A112.70 (16)N214—C42A—C24A112.91 (16)
C11—C41A—C14A120.39 (17)C21—C42A—C24A120.43 (17)
C14A—S15—C15A91.49 (8)C24A—S25—C25A91.28 (9)
N16—C15A—N114128.04 (17)N26—C25A—N214127.99 (17)
N16—C15A—S15122.38 (14)N26—C25A—S25122.17 (14)
N114—C15A—S15109.58 (12)N214—C25A—S25109.84 (12)
C15A—N16—C16A114.46 (15)C25A—N26—C26A114.72 (15)
C12A—C16A—N16123.73 (16)C22A—C26A—N26123.39 (16)
C12A—C16A—C16B120.87 (16)C22A—C26A—C26B121.20 (16)
N16—C16A—C16B115.40 (15)N26—C26A—C26B115.24 (15)
C17—C16B—C10A119.14 (16)C27—C26B—C21A119.03 (16)
C17—C16B—C16A122.04 (16)C27—C26B—C26A121.37 (16)
C10A—C16B—C16A118.82 (16)C21A—C26B—C26A119.60 (16)
C18—C17—C16B120.80 (18)C28—C27—C26B120.96 (18)
C18—C17—H17119.6C28—C27—H27119.5
C16B—C17—H17119.6C26B—C27—H27119.5
C17—C18—C19119.94 (18)C27—C28—C29119.99 (18)
C17—C18—H18120.0C27—C28—H28120.0
C19—C18—H18120.0C29—C28—H28120.0
C18—C19—C110119.54 (17)C210—C29—C28119.36 (17)
C18—C19—H19120.2C210—C29—H29120.3
C110—C19—H19120.2C28—C29—H29120.3
C10A—C110—C19121.43 (18)C29—C210—C21A121.47 (18)
C10A—C110—H110119.3C29—C210—H210119.3
C19—C110—H110119.3C21A—C210—H210119.3
C110—C10A—C16B119.12 (17)C210—C21A—C26B119.18 (17)
C110—C10A—C111122.14 (17)C210—C21A—C211120.84 (16)
C16B—C10A—C111118.67 (15)C26B—C21A—C211119.83 (15)
C10A—C111—C112112.46 (15)C21A—C211—C212114.82 (15)
C10A—C111—H11A109.1C21A—C211—H21A108.6
C112—C111—H11A109.1C212—C211—H21A108.6
C10A—C111—H11B109.1C21A—C211—H21B108.6
C112—C111—H11B109.1C212—C211—H21B108.6
H11A—C111—H11B107.8H21A—C211—H21B107.5
C12A—C112—C111111.37 (15)C22A—C212—C211113.73 (15)
C12A—C112—H11C109.4C22A—C212—H21C108.8
C111—C112—H11C109.4C211—C212—H21C108.8
C12A—C112—H11D109.4C22A—C212—H21D108.8
C111—C112—H11D109.4C211—C212—H21D108.8
H11C—C112—H11D108.0H21C—C212—H21D107.7
N114—C113—C12A109.79 (14)N214—C213—C22A110.06 (15)
N114—C113—H11E109.7N214—C213—H21E109.6
C12A—C113—H11E109.7C22A—C213—H21E109.6
N114—C113—H11F109.7N214—C213—H21F109.6
C12A—C113—H11F109.7C22A—C213—H21F109.6
H11E—C113—H11F108.2H21E—C213—H21F108.2
C16A—C12A—C113122.53 (16)C26A—C22A—C212122.44 (16)
C16A—C12A—C112121.30 (16)C26A—C22A—C213122.38 (16)
C113—C12A—C112116.15 (15)C212—C22A—C213114.87 (15)
C15A—N114—C41A115.61 (15)C25A—N214—C42A115.19 (15)
C15A—N114—C113121.29 (14)C25A—N214—C213121.29 (14)
C41A—N114—C113123.00 (15)C42A—N214—C213123.47 (15)
C41A—C11—C12—C131.5 (3)C42A—C21—C22—C232.0 (3)
C11—C12—C13—C141.1 (3)C21—C22—C23—C241.4 (3)
C11—C12—C13—Cl13179.49 (14)C21—C22—C23—Cl23179.48 (14)
C12—C13—C14—C14A0.3 (3)C22—C23—C24—C24A0.9 (3)
Cl13—C13—C14—C14A179.20 (13)Cl23—C23—C24—C24A178.28 (13)
C13—C14—C14A—C41A1.1 (3)C23—C24—C24A—C42A2.5 (3)
C13—C14—C14A—S15175.96 (14)C23—C24—C24A—S25175.99 (14)
C12—C11—C41A—N114176.01 (16)C22—C21—C42A—N214177.89 (16)
C12—C11—C41A—C14A0.7 (3)C22—C21—C42A—C24A0.3 (3)
C14—C14A—C41A—N114177.76 (15)C24—C24A—C42A—N214179.61 (16)
S15—C14A—C41A—N1140.24 (19)S25—C24A—C42A—N2141.7 (2)
C14—C14A—C41A—C110.7 (3)C24—C24A—C42A—C211.9 (3)
S15—C14A—C41A—C11176.87 (14)S25—C24A—C42A—C21176.79 (14)
C14—C14A—S15—C15A176.60 (17)C24—C24A—S25—C25A179.13 (18)
C41A—C14A—S15—C15A0.71 (14)C42A—C24A—S25—C25A0.52 (14)
C14A—S15—C15A—N16178.78 (16)C24A—S25—C25A—N26179.82 (16)
C14A—S15—C15A—N1141.46 (13)C24A—S25—C25A—N2140.73 (13)
N114—C15A—N16—C16A2.5 (3)N214—C25A—N26—C26A4.9 (3)
S15—C15A—N16—C16A177.23 (12)S25—C25A—N26—C26A174.42 (12)
C15A—N16—C16A—C12A1.1 (3)C25A—N26—C26A—C22A2.5 (3)
C15A—N16—C16A—C16B178.19 (14)C25A—N26—C26A—C26B172.69 (15)
C12A—C16A—C16B—C17162.48 (17)C22A—C26A—C26B—C27172.04 (17)
N16—C16A—C16B—C1716.9 (2)N26—C26A—C26B—C273.3 (2)
C12A—C16A—C16B—C10A16.9 (3)C22A—C26A—C26B—C21A7.1 (3)
N16—C16A—C16B—C10A163.78 (15)N26—C26A—C26B—C21A177.59 (15)
C10A—C16B—C17—C181.1 (3)C21A—C26B—C27—C280.4 (3)
C16A—C16B—C17—C18179.59 (16)C26A—C26B—C27—C28179.52 (16)
C16B—C17—C18—C190.8 (3)C26B—C27—C28—C290.7 (3)
C17—C18—C19—C1101.5 (3)C27—C28—C29—C2100.3 (3)
C18—C19—C110—C10A0.5 (3)C28—C29—C210—C21A0.5 (3)
C19—C110—C10A—C16B1.3 (3)C29—C210—C21A—C26B0.8 (3)
C19—C110—C10A—C111178.21 (17)C29—C210—C21A—C211174.68 (17)
C17—C16B—C10A—C1102.1 (3)C27—C26B—C21A—C2100.4 (3)
C16A—C16B—C10A—C110178.53 (16)C26A—C26B—C21A—C210178.77 (15)
C17—C16B—C10A—C111179.06 (16)C27—C26B—C21A—C211175.16 (16)
C16A—C16B—C10A—C1111.6 (2)C26A—C26B—C21A—C2115.7 (2)
C110—C10A—C111—C112150.19 (17)C210—C21A—C211—C212158.24 (16)
C16B—C10A—C111—C11232.9 (2)C26B—C21A—C211—C21226.3 (2)
C10A—C111—C112—C12A45.8 (2)C21A—C211—C212—C22A33.6 (2)
N16—C16A—C12A—C1132.0 (3)N26—C26A—C22A—C212172.45 (16)
C16B—C16A—C12A—C113177.32 (15)C26B—C26A—C22A—C2122.5 (3)
N16—C16A—C12A—C112179.74 (15)N26—C26A—C22A—C2130.9 (3)
C16B—C16A—C12A—C1121.0 (3)C26B—C26A—C22A—C213175.79 (15)
N114—C113—C12A—C16A0.5 (2)C211—C212—C22A—C26A23.1 (3)
N114—C113—C12A—C112177.92 (14)C211—C212—C22A—C213163.06 (15)
C111—C112—C12A—C16A30.7 (2)N214—C213—C22A—C26A2.0 (2)
C111—C112—C12A—C113150.90 (15)N214—C213—C22A—C212171.79 (14)
N16—C15A—N114—C41A178.32 (16)N26—C25A—N214—C42A178.71 (17)
S15—C15A—N114—C41A1.94 (19)S25—C25A—N214—C42A1.88 (19)
N16—C15A—N114—C1135.1 (3)N26—C25A—N214—C2133.8 (3)
S15—C15A—N114—C113174.61 (12)S25—C25A—N214—C213175.62 (12)
C11—C41A—N114—C15A175.44 (16)C21—C42A—N214—C25A176.01 (17)
C14A—C41A—N114—C15A1.4 (2)C24A—C42A—N214—C25A2.3 (2)
C11—C41A—N114—C1138.1 (3)C21—C42A—N214—C2136.6 (3)
C14A—C41A—N114—C113175.03 (15)C24A—C42A—N214—C213175.09 (15)
C12A—C113—N114—C15A3.6 (2)C22A—C213—N214—C25A0.0 (2)
C12A—C113—N114—C41A179.91 (14)C22A—C213—N214—C42A177.27 (15)

Experimental details

Crystal data
Chemical formulaC18H13ClN2S
Mr324.82
Crystal system, space groupTriclinic, P1
Temperature (K)120
a, b, c (Å)7.2637 (3), 14.4294 (5), 15.1081 (5)
α, β, γ (°)70.368 (3), 78.550 (2), 89.0800 (14)
V3)1459.56 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.40
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.924, 0.961
No. of measured, independent and
observed [I > 2σ(I)] reflections
20548, 6309, 4470
Rint0.060
(sin θ/λ)max1)0.647
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.102, 1.03
No. of reflections6309
No. of parameters397
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.38

Computer programs: KappaCCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).

Selected torsion angles (º) top
C12A—C16A—C16B—C10A16.9 (3)C22A—C26A—C26B—C21A7.1 (3)
C16A—C16B—C10A—C1111.6 (2)C26A—C26B—C21A—C2115.7 (2)
C16B—C10A—C111—C11232.9 (2)C26B—C21A—C211—C21226.3 (2)
C10A—C111—C112—C12A45.8 (2)C21A—C211—C212—C22A33.6 (2)
C16B—C16A—C12A—C1121.0 (3)C26B—C26A—C22A—C2122.5 (3)
C111—C112—C12A—C16A30.7 (2)C211—C212—C22A—C26A23.1 (3)
 

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