Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014787/ya6057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014787/ya6057Isup2.hkl |
CCDC reference: 175357
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%.
H atoms were taken into account in the riding-motion approximation with Uiso equal to 1.2Ueq of the corresonding carrier atom.
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).
C18H13ClN2S | F(000) = 672 |
Mr = 324.82 | Dx = 1.478 Mg m−3 |
Triclinic, P1 | Melting point: 452 K |
a = 7.2637 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.4294 (5) Å | Cell parameters from 20568 reflections |
c = 15.1081 (5) Å | θ = 2.9–27.5° |
α = 70.368 (3)° | µ = 0.40 mm−1 |
β = 78.550 (2)° | T = 120 K |
γ = 89.0800 (14)° | Block, orange |
V = 1459.56 (9) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Kappa-CCD diffractometer | 6309 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 4470 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ϕ scans, and ω scans with κ offsets | θmax = 27.4°, θmin = 2.9° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −9→9 |
Tmin = 0.924, Tmax = 0.961 | k = −18→18 |
20548 measured reflections | l = −18→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
C18H13ClN2S | γ = 89.0800 (14)° |
Mr = 324.82 | V = 1459.56 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.2637 (3) Å | Mo Kα radiation |
b = 14.4294 (5) Å | µ = 0.40 mm−1 |
c = 15.1081 (5) Å | T = 120 K |
α = 70.368 (3)° | 0.20 × 0.10 × 0.10 mm |
β = 78.550 (2)° |
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 = 0.961 | Rint = 0.060 |
20548 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.32 e Å−3 |
6309 reflections | Δρmin = −0.38 e Å−3 |
397 parameters |
x | y | z | Uiso*/Ueq | ||
C11 | 0.9497 (3) | 0.13006 (13) | 0.66763 (12) | 0.0210 (4) | |
C12 | 0.8722 (3) | 0.12940 (13) | 0.75932 (13) | 0.0235 (4) | |
C13 | 0.6797 (3) | 0.13427 (14) | 0.78764 (12) | 0.0241 (4) | |
Cl13 | 0.58735 (8) | 0.13428 (4) | 0.90268 (3) | 0.03721 (16) | |
C14 | 0.5574 (3) | 0.13836 (13) | 0.72597 (12) | 0.0224 (4) | |
C14A | 0.6350 (3) | 0.13698 (13) | 0.63522 (12) | 0.0197 (4) | |
C41A | 0.8302 (3) | 0.13335 (12) | 0.60551 (12) | 0.0187 (4) | |
S15 | 0.51835 (7) | 0.13400 (4) | 0.54521 (3) | 0.02312 (13) | |
C15A | 0.7328 (3) | 0.12633 (13) | 0.46944 (12) | 0.0184 (4) | |
N16 | 0.7403 (2) | 0.11994 (10) | 0.38638 (10) | 0.0183 (3) | |
C16A | 0.9261 (3) | 0.11903 (12) | 0.33377 (12) | 0.0185 (4) | |
C16B | 0.9379 (3) | 0.10865 (13) | 0.23924 (12) | 0.0186 (4) | |
C17 | 0.7835 (3) | 0.07523 (13) | 0.21374 (12) | 0.0222 (4) | |
C18 | 0.7983 (3) | 0.06674 (13) | 0.12385 (13) | 0.0258 (5) | |
C19 | 0.9677 (3) | 0.09275 (14) | 0.05758 (13) | 0.0267 (5) | |
C110 | 1.1225 (3) | 0.12491 (14) | 0.08292 (13) | 0.0259 (5) | |
C10A | 1.1115 (3) | 0.13234 (13) | 0.17268 (13) | 0.0205 (4) | |
C111 | 1.2770 (3) | 0.16999 (14) | 0.20051 (12) | 0.0241 (4) | |
C112 | 1.2746 (3) | 0.12503 (14) | 0.30755 (13) | 0.0220 (4) | |
C113 | 1.0762 (3) | 0.13229 (13) | 0.46404 (12) | 0.0202 (4) | |
C12A | 1.0824 (2) | 0.12598 (12) | 0.36654 (12) | 0.0178 (4) | |
N114 | 0.8801 (2) | 0.12882 (10) | 0.51403 (10) | 0.0172 (3) | |
C21 | −0.0308 (3) | 0.34448 (13) | −0.15182 (13) | 0.0256 (5) | |
C22 | 0.0452 (3) | 0.34242 (13) | −0.24258 (13) | 0.0277 (5) | |
C23 | 0.2377 (3) | 0.35663 (14) | −0.27785 (13) | 0.0278 (5) | |
Cl23 | 0.32929 (8) | 0.35263 (4) | −0.39189 (3) | 0.03944 (16) | |
C24 | 0.3596 (3) | 0.37532 (13) | −0.22472 (12) | 0.0262 (5) | |
C24A | 0.2820 (3) | 0.38067 (13) | −0.13546 (12) | 0.0226 (4) | |
C42A | 0.0888 (3) | 0.36402 (13) | −0.09826 (12) | 0.0203 (4) | |
S25 | 0.39665 (7) | 0.40991 (4) | −0.05581 (3) | 0.02585 (14) | |
C25A | 0.1820 (3) | 0.39806 (13) | 0.02719 (12) | 0.0188 (4) | |
N26 | 0.1730 (2) | 0.41199 (10) | 0.10724 (10) | 0.0192 (3) | |
C26A | −0.0081 (3) | 0.39046 (12) | 0.16931 (12) | 0.0172 (4) | |
C26B | −0.0152 (3) | 0.39420 (13) | 0.26629 (12) | 0.0179 (4) | |
C27 | 0.1472 (3) | 0.41247 (13) | 0.29521 (12) | 0.0219 (4) | |
C28 | 0.1393 (3) | 0.41513 (14) | 0.38667 (13) | 0.0257 (4) | |
C29 | −0.0317 (3) | 0.39838 (14) | 0.45139 (13) | 0.0261 (5) | |
C210 | −0.1935 (3) | 0.37956 (13) | 0.42335 (13) | 0.0240 (4) | |
C21A | −0.1887 (3) | 0.37777 (13) | 0.33173 (12) | 0.0192 (4) | |
C211 | −0.3683 (3) | 0.36587 (14) | 0.29940 (12) | 0.0223 (4) | |
C212 | −0.3439 (3) | 0.32751 (13) | 0.21578 (12) | 0.0215 (4) | |
C213 | −0.1543 (3) | 0.35037 (13) | 0.04946 (12) | 0.0201 (4) | |
C22A | −0.1606 (3) | 0.36143 (12) | 0.14533 (12) | 0.0176 (4) | |
N214 | 0.0372 (2) | 0.37192 (11) | −0.00789 (10) | 0.0188 (3) | |
H11 | 1.0818 | 0.1283 | 0.6476 | 0.025* | |
H12 | 0.9517 | 0.1256 | 0.8032 | 0.028* | |
H14 | 0.4257 | 0.1420 | 0.7457 | 0.027* | |
H17 | 0.6669 | 0.0581 | 0.2585 | 0.027* | |
H18 | 0.6928 | 0.0432 | 0.1076 | 0.031* | |
H19 | 0.9777 | 0.0886 | −0.0046 | 0.032* | |
H110 | 1.2383 | 0.1421 | 0.0376 | 0.031* | |
H11A | 1.2751 | 0.2425 | 0.1825 | 0.029* | |
H11B | 1.3953 | 0.1545 | 0.1641 | 0.029* | |
H11C | 1.3133 | 0.0563 | 0.3224 | 0.026* | |
H11D | 1.3662 | 0.1626 | 0.3247 | 0.026* | |
H11E | 1.1415 | 0.0767 | 0.5017 | 0.024* | |
H11F | 1.1419 | 0.1945 | 0.4576 | 0.024* | |
H21 | −0.1622 | 0.3328 | −0.1266 | 0.031* | |
H22 | −0.0350 | 0.3312 | −0.2810 | 0.033* | |
H24 | 0.4915 | 0.3841 | −0.2490 | 0.031* | |
H27 | 0.2650 | 0.4233 | 0.2515 | 0.026* | |
H28 | 0.2510 | 0.4284 | 0.4051 | 0.031* | |
H29 | −0.0378 | 0.3998 | 0.5143 | 0.031* | |
H210 | −0.3103 | 0.3676 | 0.4679 | 0.029* | |
H21A | −0.4255 | 0.4305 | 0.2808 | 0.027* | |
H21B | −0.4576 | 0.3201 | 0.3545 | 0.027* | |
H21C | −0.3527 | 0.2546 | 0.2413 | 0.026* | |
H21D | −0.4483 | 0.3493 | 0.1816 | 0.026* | |
H21E | −0.1967 | 0.2823 | 0.0588 | 0.024* | |
H21F | −0.2404 | 0.3961 | 0.0152 | 0.024* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C11 | 0.0210 (11) | 0.0209 (10) | 0.0218 (10) | 0.0010 (8) | −0.0068 (8) | −0.0069 (8) |
C12 | 0.0275 (12) | 0.0232 (11) | 0.0211 (10) | −0.0005 (9) | −0.0088 (8) | −0.0068 (8) |
C13 | 0.0300 (12) | 0.0251 (11) | 0.0166 (10) | 0.0022 (9) | −0.0049 (8) | −0.0064 (8) |
Cl13 | 0.0376 (3) | 0.0555 (4) | 0.0200 (3) | 0.0023 (3) | −0.0037 (2) | −0.0159 (2) |
C14 | 0.0198 (11) | 0.0237 (11) | 0.0218 (10) | 0.0021 (8) | −0.0016 (8) | −0.0067 (8) |
C14A | 0.0188 (11) | 0.0203 (10) | 0.0199 (10) | 0.0016 (8) | −0.0060 (8) | −0.0054 (8) |
C41A | 0.0205 (11) | 0.0156 (10) | 0.0191 (10) | −0.0003 (8) | −0.0031 (8) | −0.0053 (7) |
S15 | 0.0153 (3) | 0.0354 (3) | 0.0206 (3) | 0.0030 (2) | −0.00396 (19) | −0.0118 (2) |
C15A | 0.0151 (10) | 0.0192 (10) | 0.0203 (10) | 0.0006 (8) | −0.0044 (7) | −0.0054 (7) |
N16 | 0.0153 (9) | 0.0237 (9) | 0.0161 (8) | 0.0023 (7) | −0.0022 (6) | −0.0076 (6) |
C16A | 0.0171 (10) | 0.0156 (10) | 0.0202 (10) | 0.0008 (7) | −0.0011 (8) | −0.0043 (7) |
C16B | 0.0192 (10) | 0.0166 (10) | 0.0199 (10) | 0.0048 (8) | −0.0047 (8) | −0.0058 (7) |
C17 | 0.0219 (11) | 0.0234 (11) | 0.0220 (10) | 0.0019 (8) | −0.0047 (8) | −0.0085 (8) |
C18 | 0.0301 (12) | 0.0250 (11) | 0.0267 (11) | 0.0023 (9) | −0.0105 (9) | −0.0119 (8) |
C19 | 0.0360 (13) | 0.0259 (11) | 0.0202 (10) | 0.0060 (9) | −0.0054 (9) | −0.0108 (8) |
C110 | 0.0259 (12) | 0.0264 (11) | 0.0239 (11) | 0.0043 (9) | 0.0000 (8) | −0.0095 (8) |
C10A | 0.0209 (11) | 0.0164 (10) | 0.0220 (10) | 0.0048 (8) | −0.0028 (8) | −0.0049 (7) |
C111 | 0.0186 (11) | 0.0245 (11) | 0.0246 (11) | 0.0004 (8) | 0.0011 (8) | −0.0053 (8) |
C112 | 0.0166 (10) | 0.0213 (10) | 0.0265 (10) | 0.0004 (8) | −0.0027 (8) | −0.0069 (8) |
C113 | 0.0149 (10) | 0.0215 (10) | 0.0239 (10) | −0.0009 (8) | −0.0039 (8) | −0.0075 (8) |
C12A | 0.0156 (10) | 0.0171 (10) | 0.0196 (10) | −0.0004 (8) | −0.0025 (8) | −0.0052 (7) |
N114 | 0.0133 (8) | 0.0221 (9) | 0.0176 (8) | 0.0022 (6) | −0.0047 (6) | −0.0075 (6) |
C21 | 0.0315 (12) | 0.0238 (11) | 0.0223 (11) | −0.0005 (9) | −0.0069 (9) | −0.0080 (8) |
C22 | 0.0389 (14) | 0.0232 (11) | 0.0243 (11) | 0.0031 (9) | −0.0118 (9) | −0.0095 (8) |
C23 | 0.0428 (14) | 0.0241 (11) | 0.0176 (10) | 0.0100 (9) | −0.0077 (9) | −0.0080 (8) |
Cl23 | 0.0512 (4) | 0.0497 (4) | 0.0218 (3) | 0.0189 (3) | −0.0085 (2) | −0.0179 (2) |
C24 | 0.0264 (12) | 0.0297 (12) | 0.0202 (11) | 0.0083 (9) | −0.0014 (8) | −0.0077 (8) |
C24A | 0.0236 (11) | 0.0234 (11) | 0.0214 (10) | 0.0056 (8) | −0.0068 (8) | −0.0073 (8) |
C42A | 0.0260 (12) | 0.0169 (10) | 0.0173 (10) | 0.0022 (8) | −0.0036 (8) | −0.0053 (7) |
S25 | 0.0174 (3) | 0.0404 (3) | 0.0201 (3) | 0.0031 (2) | −0.0030 (2) | −0.0114 (2) |
C25A | 0.0168 (10) | 0.0189 (10) | 0.0197 (10) | 0.0014 (8) | −0.0042 (8) | −0.0053 (7) |
N26 | 0.0172 (9) | 0.0238 (9) | 0.0157 (8) | 0.0001 (7) | −0.0016 (6) | −0.0063 (6) |
C26A | 0.0162 (10) | 0.0148 (9) | 0.0192 (10) | 0.0023 (7) | −0.0037 (8) | −0.0040 (7) |
C26B | 0.0192 (11) | 0.0168 (10) | 0.0171 (9) | 0.0024 (8) | −0.0043 (7) | −0.0050 (7) |
C27 | 0.0180 (11) | 0.0260 (11) | 0.0223 (10) | 0.0020 (8) | −0.0049 (8) | −0.0086 (8) |
C28 | 0.0247 (11) | 0.0316 (12) | 0.0262 (11) | 0.0043 (9) | −0.0111 (9) | −0.0138 (9) |
C29 | 0.0320 (13) | 0.0297 (11) | 0.0187 (10) | 0.0039 (9) | −0.0047 (9) | −0.0115 (8) |
C210 | 0.0231 (11) | 0.0267 (11) | 0.0208 (10) | 0.0004 (9) | −0.0001 (8) | −0.0085 (8) |
C21A | 0.0197 (11) | 0.0157 (10) | 0.0208 (10) | −0.0001 (8) | −0.0017 (8) | −0.0056 (7) |
C211 | 0.0157 (10) | 0.0250 (11) | 0.0233 (10) | −0.0019 (8) | 0.0001 (8) | −0.0067 (8) |
C212 | 0.0162 (10) | 0.0243 (11) | 0.0218 (10) | −0.0017 (8) | −0.0036 (8) | −0.0050 (8) |
C213 | 0.0154 (10) | 0.0226 (10) | 0.0227 (10) | −0.0017 (8) | −0.0034 (8) | −0.0084 (8) |
C22A | 0.0179 (10) | 0.0167 (10) | 0.0173 (9) | 0.0019 (8) | −0.0040 (7) | −0.0046 (7) |
N214 | 0.0161 (9) | 0.0237 (9) | 0.0170 (8) | −0.0004 (7) | −0.0023 (6) | −0.0082 (6) |
C11—C12 | 1.385 (3) | C21—C22 | 1.383 (3) |
C11—C41A | 1.389 (2) | C21—C42A | 1.389 (3) |
C11—H11 | 0.9500 | C21—H21 | 0.9500 |
C12—C13 | 1.386 (3) | C22—C23 | 1.386 (3) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
C13—C14 | 1.397 (3) | C23—C24 | 1.391 (3) |
C13—Cl13 | 1.7345 (18) | C23—Cl23 | 1.7391 (18) |
C14—C14A | 1.382 (2) | C24—C24A | 1.382 (2) |
C14—H14 | 0.9500 | C24—H24 | 0.9500 |
C14A—C41A | 1.405 (3) | C24A—C42A | 1.397 (3) |
C14A—S15 | 1.7515 (18) | C24A—S25 | 1.7519 (18) |
C41A—N114 | 1.381 (2) | C42A—N214 | 1.385 (2) |
S15—C15A | 1.7667 (18) | S25—C25A | 1.7667 (18) |
C15A—N16 | 1.279 (2) | C25A—N26 | 1.280 (2) |
C15A—N114 | 1.379 (2) | C25A—N214 | 1.377 (2) |
N16—C16A | 1.426 (2) | N26—C26A | 1.426 (2) |
C16A—C12A | 1.343 (2) | C26A—C22A | 1.346 (2) |
C16A—C16B | 1.471 (2) | C26A—C26B | 1.475 (2) |
C16B—C17 | 1.397 (3) | C26B—C27 | 1.394 (2) |
C16B—C10A | 1.414 (2) | C26B—C21A | 1.407 (2) |
C17—C18 | 1.387 (2) | C27—C28 | 1.385 (2) |
C17—H17 | 0.9500 | C27—H27 | 0.9500 |
C18—C19 | 1.389 (3) | C28—C29 | 1.388 (3) |
C18—H18 | 0.9500 | C28—H28 | 0.9500 |
C19—C110 | 1.390 (3) | C29—C210 | 1.386 (3) |
C19—H19 | 0.9500 | C29—H29 | 0.9500 |
C110—C10A | 1.383 (2) | C210—C21A | 1.387 (2) |
C110—H110 | 0.9500 | C210—H210 | 0.9500 |
C10A—C111 | 1.514 (3) | C21A—C211 | 1.512 (3) |
C111—C112 | 1.523 (2) | C211—C212 | 1.520 (2) |
C111—H11A | 0.9900 | C211—H21A | 0.9900 |
C111—H11B | 0.9900 | C211—H21B | 0.9900 |
C112—C12A | 1.502 (2) | C212—C22A | 1.501 (2) |
C112—H11C | 0.9900 | C212—H21C | 0.9900 |
C112—H11D | 0.9900 | C212—H21D | 0.9900 |
C113—N114 | 1.467 (2) | C213—N214 | 1.462 (2) |
C113—C12A | 1.498 (2) | C213—C22A | 1.501 (2) |
C113—H11E | 0.9900 | C213—H21E | 0.9900 |
C113—H11F | 0.9900 | C213—H21F | 0.9900 |
C12—C11—C41A | 118.63 (18) | C22—C21—C42A | 118.71 (19) |
C12—C11—H11 | 120.7 | C22—C21—H21 | 120.6 |
C41A—C11—H11 | 120.7 | C42A—C21—H21 | 120.6 |
C11—C12—C13 | 120.60 (18) | C21—C22—C23 | 120.38 (18) |
C11—C12—H12 | 119.7 | C21—C22—H22 | 119.8 |
C13—C12—H12 | 119.7 | C23—C22—H22 | 119.8 |
C12—C13—C14 | 121.61 (17) | C22—C23—C24 | 121.59 (18) |
C12—C13—Cl13 | 119.46 (14) | C22—C23—Cl23 | 119.31 (15) |
C14—C13—Cl13 | 118.93 (15) | C24—C23—Cl23 | 119.09 (16) |
C14A—C14—C13 | 117.56 (18) | C24A—C24—C23 | 117.71 (19) |
C14A—C14—H14 | 121.2 | C24A—C24—H24 | 121.1 |
C13—C14—H14 | 121.2 | C23—C24—H24 | 121.1 |
C14—C14A—C41A | 121.20 (17) | C24—C24A—C42A | 121.11 (17) |
C14—C14A—S15 | 128.15 (15) | C24—C24A—S25 | 128.13 (16) |
C41A—C14A—S15 | 110.59 (13) | C42A—C24A—S25 | 110.74 (13) |
N114—C41A—C11 | 126.85 (17) | N214—C42A—C21 | 126.64 (18) |
N114—C41A—C14A | 112.70 (16) | N214—C42A—C24A | 112.91 (16) |
C11—C41A—C14A | 120.39 (17) | C21—C42A—C24A | 120.43 (17) |
C14A—S15—C15A | 91.49 (8) | C24A—S25—C25A | 91.28 (9) |
N16—C15A—N114 | 128.04 (17) | N26—C25A—N214 | 127.99 (17) |
N16—C15A—S15 | 122.38 (14) | N26—C25A—S25 | 122.17 (14) |
N114—C15A—S15 | 109.58 (12) | N214—C25A—S25 | 109.84 (12) |
C15A—N16—C16A | 114.46 (15) | C25A—N26—C26A | 114.72 (15) |
C12A—C16A—N16 | 123.73 (16) | C22A—C26A—N26 | 123.39 (16) |
C12A—C16A—C16B | 120.87 (16) | C22A—C26A—C26B | 121.20 (16) |
N16—C16A—C16B | 115.40 (15) | N26—C26A—C26B | 115.24 (15) |
C17—C16B—C10A | 119.14 (16) | C27—C26B—C21A | 119.03 (16) |
C17—C16B—C16A | 122.04 (16) | C27—C26B—C26A | 121.37 (16) |
C10A—C16B—C16A | 118.82 (16) | C21A—C26B—C26A | 119.60 (16) |
C18—C17—C16B | 120.80 (18) | C28—C27—C26B | 120.96 (18) |
C18—C17—H17 | 119.6 | C28—C27—H27 | 119.5 |
C16B—C17—H17 | 119.6 | C26B—C27—H27 | 119.5 |
C17—C18—C19 | 119.94 (18) | C27—C28—C29 | 119.99 (18) |
C17—C18—H18 | 120.0 | C27—C28—H28 | 120.0 |
C19—C18—H18 | 120.0 | C29—C28—H28 | 120.0 |
C18—C19—C110 | 119.54 (17) | C210—C29—C28 | 119.36 (17) |
C18—C19—H19 | 120.2 | C210—C29—H29 | 120.3 |
C110—C19—H19 | 120.2 | C28—C29—H29 | 120.3 |
C10A—C110—C19 | 121.43 (18) | C29—C210—C21A | 121.47 (18) |
C10A—C110—H110 | 119.3 | C29—C210—H210 | 119.3 |
C19—C110—H110 | 119.3 | C21A—C210—H210 | 119.3 |
C110—C10A—C16B | 119.12 (17) | C210—C21A—C26B | 119.18 (17) |
C110—C10A—C111 | 122.14 (17) | C210—C21A—C211 | 120.84 (16) |
C16B—C10A—C111 | 118.67 (15) | C26B—C21A—C211 | 119.83 (15) |
C10A—C111—C112 | 112.46 (15) | C21A—C211—C212 | 114.82 (15) |
C10A—C111—H11A | 109.1 | C21A—C211—H21A | 108.6 |
C112—C111—H11A | 109.1 | C212—C211—H21A | 108.6 |
C10A—C111—H11B | 109.1 | C21A—C211—H21B | 108.6 |
C112—C111—H11B | 109.1 | C212—C211—H21B | 108.6 |
H11A—C111—H11B | 107.8 | H21A—C211—H21B | 107.5 |
C12A—C112—C111 | 111.37 (15) | C22A—C212—C211 | 113.73 (15) |
C12A—C112—H11C | 109.4 | C22A—C212—H21C | 108.8 |
C111—C112—H11C | 109.4 | C211—C212—H21C | 108.8 |
C12A—C112—H11D | 109.4 | C22A—C212—H21D | 108.8 |
C111—C112—H11D | 109.4 | C211—C212—H21D | 108.8 |
H11C—C112—H11D | 108.0 | H21C—C212—H21D | 107.7 |
N114—C113—C12A | 109.79 (14) | N214—C213—C22A | 110.06 (15) |
N114—C113—H11E | 109.7 | N214—C213—H21E | 109.6 |
C12A—C113—H11E | 109.7 | C22A—C213—H21E | 109.6 |
N114—C113—H11F | 109.7 | N214—C213—H21F | 109.6 |
C12A—C113—H11F | 109.7 | C22A—C213—H21F | 109.6 |
H11E—C113—H11F | 108.2 | H21E—C213—H21F | 108.2 |
C16A—C12A—C113 | 122.53 (16) | C26A—C22A—C212 | 122.44 (16) |
C16A—C12A—C112 | 121.30 (16) | C26A—C22A—C213 | 122.38 (16) |
C113—C12A—C112 | 116.15 (15) | C212—C22A—C213 | 114.87 (15) |
C15A—N114—C41A | 115.61 (15) | C25A—N214—C42A | 115.19 (15) |
C15A—N114—C113 | 121.29 (14) | C25A—N214—C213 | 121.29 (14) |
C41A—N114—C113 | 123.00 (15) | C42A—N214—C213 | 123.47 (15) |
C41A—C11—C12—C13 | −1.5 (3) | C42A—C21—C22—C23 | 2.0 (3) |
C11—C12—C13—C14 | 1.1 (3) | C21—C22—C23—C24 | −1.4 (3) |
C11—C12—C13—Cl13 | −179.49 (14) | C21—C22—C23—Cl23 | 179.48 (14) |
C12—C13—C14—C14A | 0.3 (3) | C22—C23—C24—C24A | −0.9 (3) |
Cl13—C13—C14—C14A | −179.20 (13) | Cl23—C23—C24—C24A | 178.28 (13) |
C13—C14—C14A—C41A | −1.1 (3) | C23—C24—C24A—C42A | 2.5 (3) |
C13—C14—C14A—S15 | 175.96 (14) | C23—C24—C24A—S25 | −175.99 (14) |
C12—C11—C41A—N114 | −176.01 (16) | C22—C21—C42A—N214 | 177.89 (16) |
C12—C11—C41A—C14A | 0.7 (3) | C22—C21—C42A—C24A | −0.3 (3) |
C14—C14A—C41A—N114 | 177.76 (15) | C24—C24A—C42A—N214 | 179.61 (16) |
S15—C14A—C41A—N114 | 0.24 (19) | S25—C24A—C42A—N214 | −1.7 (2) |
C14—C14A—C41A—C11 | 0.7 (3) | C24—C24A—C42A—C21 | −1.9 (3) |
S15—C14A—C41A—C11 | −176.87 (14) | S25—C24A—C42A—C21 | 176.79 (14) |
C14—C14A—S15—C15A | −176.60 (17) | C24—C24A—S25—C25A | 179.13 (18) |
C41A—C14A—S15—C15A | 0.71 (14) | C42A—C24A—S25—C25A | 0.52 (14) |
C14A—S15—C15A—N16 | 178.78 (16) | C24A—S25—C25A—N26 | −179.82 (16) |
C14A—S15—C15A—N114 | −1.46 (13) | C24A—S25—C25A—N214 | 0.73 (13) |
N114—C15A—N16—C16A | −2.5 (3) | N214—C25A—N26—C26A | 4.9 (3) |
S15—C15A—N16—C16A | 177.23 (12) | S25—C25A—N26—C26A | −174.42 (12) |
C15A—N16—C16A—C12A | −1.1 (3) | C25A—N26—C26A—C22A | −2.5 (3) |
C15A—N16—C16A—C16B | 178.19 (14) | C25A—N26—C26A—C26B | 172.69 (15) |
C12A—C16A—C16B—C17 | 162.48 (17) | C22A—C26A—C26B—C27 | 172.04 (17) |
N16—C16A—C16B—C17 | −16.9 (2) | N26—C26A—C26B—C27 | −3.3 (2) |
C12A—C16A—C16B—C10A | −16.9 (3) | C22A—C26A—C26B—C21A | −7.1 (3) |
N16—C16A—C16B—C10A | 163.78 (15) | N26—C26A—C26B—C21A | 177.59 (15) |
C10A—C16B—C17—C18 | −1.1 (3) | C21A—C26B—C27—C28 | −0.4 (3) |
C16A—C16B—C17—C18 | 179.59 (16) | C26A—C26B—C27—C28 | −179.52 (16) |
C16B—C17—C18—C19 | −0.8 (3) | C26B—C27—C28—C29 | 0.7 (3) |
C17—C18—C19—C110 | 1.5 (3) | C27—C28—C29—C210 | −0.3 (3) |
C18—C19—C110—C10A | −0.5 (3) | C28—C29—C210—C21A | −0.5 (3) |
C19—C110—C10A—C16B | −1.3 (3) | C29—C210—C21A—C26B | 0.8 (3) |
C19—C110—C10A—C111 | −178.21 (17) | C29—C210—C21A—C211 | −174.68 (17) |
C17—C16B—C10A—C110 | 2.1 (3) | C27—C26B—C21A—C210 | −0.4 (3) |
C16A—C16B—C10A—C110 | −178.53 (16) | C26A—C26B—C21A—C210 | 178.77 (15) |
C17—C16B—C10A—C111 | 179.06 (16) | C27—C26B—C21A—C211 | 175.16 (16) |
C16A—C16B—C10A—C111 | −1.6 (2) | C26A—C26B—C21A—C211 | −5.7 (2) |
C110—C10A—C111—C112 | −150.19 (17) | C210—C21A—C211—C212 | −158.24 (16) |
C16B—C10A—C111—C112 | 32.9 (2) | C26B—C21A—C211—C212 | 26.3 (2) |
C10A—C111—C112—C12A | −45.8 (2) | C21A—C211—C212—C22A | −33.6 (2) |
N16—C16A—C12A—C113 | 2.0 (3) | N26—C26A—C22A—C212 | 172.45 (16) |
C16B—C16A—C12A—C113 | −177.32 (15) | C26B—C26A—C22A—C212 | −2.5 (3) |
N16—C16A—C12A—C112 | −179.74 (15) | N26—C26A—C22A—C213 | −0.9 (3) |
C16B—C16A—C12A—C112 | 1.0 (3) | C26B—C26A—C22A—C213 | −175.79 (15) |
N114—C113—C12A—C16A | 0.5 (2) | C211—C212—C22A—C26A | 23.1 (3) |
N114—C113—C12A—C112 | −177.92 (14) | C211—C212—C22A—C213 | −163.06 (15) |
C111—C112—C12A—C16A | 30.7 (2) | N214—C213—C22A—C26A | 2.0 (2) |
C111—C112—C12A—C113 | −150.90 (15) | N214—C213—C22A—C212 | −171.79 (14) |
N16—C15A—N114—C41A | −178.32 (16) | N26—C25A—N214—C42A | 178.71 (17) |
S15—C15A—N114—C41A | 1.94 (19) | S25—C25A—N214—C42A | −1.88 (19) |
N16—C15A—N114—C113 | 5.1 (3) | N26—C25A—N214—C213 | −3.8 (3) |
S15—C15A—N114—C113 | −174.61 (12) | S25—C25A—N214—C213 | 175.62 (12) |
C11—C41A—N114—C15A | 175.44 (16) | C21—C42A—N214—C25A | −176.01 (17) |
C14A—C41A—N114—C15A | −1.4 (2) | C24A—C42A—N214—C25A | 2.3 (2) |
C11—C41A—N114—C113 | −8.1 (3) | C21—C42A—N214—C213 | 6.6 (3) |
C14A—C41A—N114—C113 | 175.03 (15) | C24A—C42A—N214—C213 | −175.09 (15) |
C12A—C113—N114—C15A | −3.6 (2) | C22A—C213—N214—C25A | 0.0 (2) |
C12A—C113—N114—C41A | −179.91 (14) | C22A—C213—N214—C42A | 177.27 (15) |
Experimental details
Crystal data | |
Chemical formula | C18H13ClN2S |
Mr | 324.82 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1459.56 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.20 × 0.10 × 0.10 |
Data collection | |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.924, 0.961 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20548, 6309, 4470 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.647 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.102, 1.03 |
No. of reflections | 6309 |
No. of parameters | 397 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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).
C12A—C16A—C16B—C10A | −16.9 (3) | C22A—C26A—C26B—C21A | −7.1 (3) |
C16A—C16B—C10A—C111 | −1.6 (2) | C26A—C26B—C21A—C211 | −5.7 (2) |
C16B—C10A—C111—C112 | 32.9 (2) | C26B—C21A—C211—C212 | 26.3 (2) |
C10A—C111—C112—C12A | −45.8 (2) | C21A—C211—C212—C22A | −33.6 (2) |
C16B—C16A—C12A—C112 | 1.0 (3) | C26B—C26A—C22A—C212 | −2.5 (3) |
C111—C112—C12A—C16A | 30.7 (2) | C211—C212—C22A—C26A | 23.1 (3) |
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.