Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100012397/gs1110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100012397/gs1110IVsup2.hkl |
CCDC reference: 156159
A mixture of 2-aminobenzothiazole (2 mmol) and 3-(dimethylamino)-1-(2-hydroxyphenyl)-1-propanone hydrochloride (2 mmol) in ethanol (5 ml) was heated to reflux for 10 min. Yellow crystals appeared in hot solution and were filtered out without cooling, washed with fresh ethanol and dried to give the title compound. Suitable crystals for X-ray diffraction were obtained after recrystallization from ethanol (yield 45%, m.p. 252 K). Analysis, calculated for C25H19NO4S: C 69.9, H 4.46%, N 3.26%; found: C 70.17, H 4.27, N 3.14%.
Molecule (IV) crystallized in the monoclinic system; space group P21/n from the systematic absences. H atoms were treated as riding atoms with C—H 0.95 to 1.00 Å, O—H 0.9293 and 1.0269 Å. The hydroxyl H atom positions were determined from a difference map.
Data collection: Kappa-CCD Server Software (Nonius, 1997); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2000); software used to prepare material for publication: SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
C25H19NO4S | Z = 2 |
Mr = 429.47 | F(000) = 448 |
Triclinic, P1 | Dx = 1.477 Mg m−3 |
a = 7.4978 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.265 (2) Å | Cell parameters from 4393 reflections |
c = 12.322 (3) Å | θ = 3.0–27.5° |
α = 108.12 (3)° | µ = 0.20 mm−1 |
β = 99.38 (3)° | T = 150 K |
γ = 94.75 (3)° | Block, yellow |
V = 966.0 (3) Å3 | 0.22 × 0.15 × 0.15 mm |
Kappa-CCD diffractometer | 4393 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 3506 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ϕ scans and ω scans with κ offsets | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995 & 1997) | h = −9→9 |
Tmin = 0.956, Tmax = 0.970 | k = −14→13 |
14805 measured reflections | l = −15→15 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.2149P] where P = (Fo2 + 2Fc2)/3 |
4393 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C25H19NO4S | γ = 94.75 (3)° |
Mr = 429.47 | V = 966.0 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4978 (15) Å | Mo Kα radiation |
b = 11.265 (2) Å | µ = 0.20 mm−1 |
c = 12.322 (3) Å | T = 150 K |
α = 108.12 (3)° | 0.22 × 0.15 × 0.15 mm |
β = 99.38 (3)° |
Kappa-CCD diffractometer | 4393 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995 & 1997) | 3506 reflections with I > 2σ(I) |
Tmin = 0.956, Tmax = 0.970 | Rint = 0.039 |
14805 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.111 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.25 e Å−3 |
4393 reflections | Δρmin = −0.33 e Å−3 |
280 parameters |
Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.3029 (0.0039) x − 1.6209 (0.0039) y + 0.7940 (0.0060) z = 1.0215 (0.0019) * 0.0075 (0.0011) N1 * −0.0164 (0.0010) C2 * −0.0084 (0.0008) S3 * 0.0195 (0.0013) C4A * 0.0154 (0.0013) C7A * −0.0039 (0.0012) C7 * −0.0099 (0.0013) C6 * −0.0076 (0.0013) C5 * 0.0038 (0.0012) C4 Rms deviation of fitted atoms = 0.0115 − 6.6000 (0.0042) x + 4.0752 (0.0073) y − 3.7065 (0.0081) z = 0.8765 (0.0061) Angle to previous plane (with approximate e.s.d.) = 16.77 (0.06) * −0.0322 (0.0010) C22 * 0.0287 (0.0011) C23 * −0.0020 (0.0012) C24 * −0.0215 (0.0012) C25 * 0.0171 (0.0012) C26 * 0.0099 (0.0011) C27 − 0.1186 (0.0023) C21 0.2236 (0.0025) O22 0.1099 (0.0022) O23 Rms deviation of fitted atoms = 0.0213 7.4914 (0.0039) x − 0.9841 (0.0071) y − 1.5187 (0.0077) z = 1.3123 (0.0027) Angle to previous plane (with approximate e.s.d.) = 26.33 (0.05) * 0.0298 (0.0010) N1 * 0.1173 (0.0010) C2 * −0.0390 (0.0010) C11 * −0.1953 (0.0010) C10 * 0.3599 (0.0011) C9 * −0.2727 (0.0011) C8 Rms deviation of fitted atoms = 0.2075 7.3478 (0.0040) x − 1.6648 (0.0070) y + 0.4516 (0.0093) z = 1.0099 (0.0027) Angle to previous plane (with approximate e.s.d.) = 9.20 (0.04) * 0.0330 (0.0010) N1 * 0.0101 (0.0010) C2 * −0.0462 (0.0010) C11 * 0.0402 (0.0007) C10 * −0.0371 (0.0007) C8 0.6909 (0.0021) C9 Rms deviation of fitted atoms = 0.0355 7.2980 (0.0040) x − 1.4730 (0.0063) y + 0.8146 (0.0071) z = 1.0606 (0.0023) Angle to previous plane (with approximate e.s.d.) = 2.31 (0.05) * 0.0048 (0.0009) N1 * −0.0026 (0.0008) C2 * −0.0001 (0.0007) S3 * 0.0027 (0.0008) C4A * −0.0047 (0.0009) C7A Rms deviation of fitted atoms = 0.0034 7.4914 (0.0039) x − 0.9841 (0.0071) y − 1.5187 (0.0077) z = 1.3123 (0.0027) Angle to previous plane (with approximate e.s.d.) = 10.91 (0.04) * 0.0298 (0.0010) N1 * 0.1173 (0.0010) C2 * −0.0390 (0.0010) C11 * −0.1953 (0.0010) C10 * 0.3599 (0.0011) C9 * −0.2727 (0.0011) C8 Rms deviation of fitted atoms = 0.2075 7.2980 (0.0040) x − 1.4730 (0.0063) y + 0.8146 (0.0071) z = 1.0606 (0.0023) Angle to previous plane (with approximate e.s.d.) = 10.91 (0.04) * 0.0048 (0.0009) N1 * −0.0026 (0.0008) C2 * −0.0001 (0.0007) S3 * 0.0027 (0.0008) C4A * −0.0047 (0.0009) C7A Rms deviation of fitted atoms = 0.0034 7.3044 (0.0040) x − 1.7387 (0.0074) y + 0.7873 (0.0085) z = 1.0185 (0.0027) Angle to previous plane (with approximate e.s.d.) = 1.48 (0.05) * 0.0017 (0.0011) C4A * 0.0012 (0.0011) C7A * −0.0031 (0.0011) C7 * 0.0021 (0.0012) C6 * 0.0008 (0.0012) C5 * −0.0027 (0.0012) C4 Rms deviation of fitted atoms = 0.0021 7.3984 (0.0039) x − 1.3092 (0.0035) y − 0.0231 (0.0037) z = 1.2618 (0.0015) Angle to previous plane (with approximate e.s.d.) = 3.93 (0.04) * −0.0939 (0.0012) N1 * −0.0678 (0.0013) C2 * −0.1261 (0.0012) C11 * −0.0993 (0.0013) C10 * 0.5058 (0.0013) C9 * −0.2226 (0.0014) C8 * 0.0541 (0.0008) S3 * 0.0580 (0.0014) C4A * −0.0378 (0.0014) C7A * −0.0912 (0.0014) C7 * −0.0377 (0.0014) C6 * 0.0565 (0.0015) C5 * 0.1019 (0.0014) C4 Rms deviation of fitted atoms = 0.1700 − 6.6000 (0.0042) x + 4.0752 (0.0073) y − 3.7065 (0.0081) z = 0.8765 (0.0061) Angle to previous plane (with approximate e.s.d.) = 20.25 (0.05) * −0.0322 (0.0010) C22 * 0.0287 (0.0011) C23 * −0.0020 (0.0012) C24 * −0.0215 (0.0012) C25 * 0.0171 (0.0012) C26 * 0.0099 (0.0011) C27 Rms deviation of fitted atoms = 0.0213 − 1.6998 (0.0049) x + 9.3510 (0.0064) y + 3.3241 (0.0081) z = 3.7445 (0.0040) Angle to previous plane (with approximate e.s.d.) = 76.43 (0.06) * −0.0112 (0.0011) C14 * 0.0183 (0.0011) C15 * −0.0103 (0.0012) C16 * −0.0050 (0.0012) C17 * 0.0120 (0.0012) C18 * −0.0039 (0.0011) C19 − 0.0671 (0.0025) C12 0.0826 (0.0027) O13 0.0465 (0.0023) O15 Rms deviation of fitted atoms = 0.0112 7.3029 (0.0039) x − 1.6209 (0.0039) y + 0.7940 (0.0060) z = 1.0215 (0.0019) Angle to previous plane (with approximate e.s.d.) = 81.01 (0.05) * 0.0075 (0.0011) N1 * −0.0164 (0.0010) C2 * −0.0084 (0.0008) S3 * 0.0195 (0.0013) C4A * 0.0154 (0.0013) C7A * −0.0039 (0.0012) C7 * −0.0099 (0.0013) C6 * −0.0076 (0.0013) C5 * 0.0038 (0.0012) C4 Rms deviation of fitted atoms = 0.0115 |
x | y | z | Uiso*/Ueq | ||
N1 | 0.20366 (17) | 0.25960 (12) | −0.04732 (10) | 0.0237 (3) | |
C2 | 0.22741 (19) | 0.37418 (14) | −0.06199 (13) | 0.0230 (3) | |
S3 | 0.24046 (5) | 0.35729 (4) | −0.20631 (3) | 0.02600 (12) | |
C4 | 0.2014 (2) | 0.10249 (16) | −0.35162 (14) | 0.0325 (4) | |
C4A | 0.2117 (2) | 0.19239 (15) | −0.24326 (14) | 0.0267 (3) | |
C5 | 0.1729 (2) | −0.02376 (16) | −0.36146 (15) | 0.0352 (4) | |
C6 | 0.1541 (2) | −0.05965 (16) | −0.26489 (14) | 0.0333 (4) | |
C7 | 0.1629 (2) | 0.02904 (15) | −0.15719 (14) | 0.0292 (4) | |
C7A | 0.1925 (2) | 0.15571 (15) | −0.14726 (13) | 0.0257 (3) | |
C8 | 0.1844 (2) | 0.24727 (15) | 0.06499 (13) | 0.0265 (3) | |
C9 | 0.3030 (2) | 0.35906 (14) | 0.16069 (12) | 0.0248 (3) | |
C10 | 0.2429 (2) | 0.48209 (15) | 0.15036 (13) | 0.0248 (3) | |
C11 | 0.24005 (19) | 0.48849 (14) | 0.02915 (13) | 0.0227 (3) | |
C12 | 0.2835 (2) | 0.34616 (14) | 0.27747 (13) | 0.0248 (3) | |
O13 | 0.12733 (15) | 0.32762 (12) | 0.29478 (10) | 0.0338 (3) | |
C14 | 0.4439 (2) | 0.35016 (14) | 0.36504 (13) | 0.0243 (3) | |
C15 | 0.4194 (2) | 0.31428 (14) | 0.46234 (13) | 0.0280 (3) | |
O15 | 0.25259 (16) | 0.28063 (12) | 0.48018 (10) | 0.0368 (3) | |
C16 | 0.5700 (2) | 0.31000 (16) | 0.54274 (14) | 0.0345 (4) | |
C17 | 0.7441 (2) | 0.34662 (17) | 0.53040 (15) | 0.0374 (4) | |
C18 | 0.7709 (2) | 0.38635 (17) | 0.43742 (14) | 0.0346 (4) | |
C19 | 0.6225 (2) | 0.38677 (15) | 0.35556 (13) | 0.0282 (3) | |
C21 | 0.25597 (19) | 0.60106 (14) | 0.00058 (13) | 0.0232 (3) | |
C22 | 0.27510 (19) | 0.73090 (14) | 0.08596 (13) | 0.0238 (3) | |
O22 | 0.25849 (15) | 0.59285 (10) | −0.10525 (9) | 0.0285 (3) | |
C23 | 0.3465 (2) | 0.83447 (15) | 0.05621 (14) | 0.0273 (3) | |
O23 | 0.38526 (17) | 0.81974 (11) | −0.05084 (10) | 0.0352 (3) | |
C24 | 0.3813 (2) | 0.95588 (15) | 0.13599 (15) | 0.0320 (4) | |
C25 | 0.3378 (2) | 0.97916 (16) | 0.24438 (15) | 0.0345 (4) | |
C26 | 0.2553 (2) | 0.88126 (16) | 0.27329 (14) | 0.0328 (4) | |
C27 | 0.2253 (2) | 0.75987 (15) | 0.19514 (13) | 0.0273 (3) | |
H4 | 0.2136 | 0.1270 | −0.4175 | 0.039* | |
H5 | 0.1660 | −0.0866 | −0.4349 | 0.042* | |
H6 | 0.1349 | −0.1468 | −0.2735 | 0.040* | |
H7 | 0.1491 | 0.0043 | −0.0917 | 0.035* | |
H8A | 0.2239 | 0.1673 | 0.0706 | 0.032* | |
H8B | 0.0552 | 0.2465 | 0.0731 | 0.032* | |
H9 | 0.4334 | 0.3578 | 0.1526 | 0.030* | |
H10A | 0.1194 | 0.4885 | 0.1684 | 0.030* | |
H10B | 0.3278 | 0.5544 | 0.2080 | 0.030* | |
H151 | 0.1634 | 0.2919 | 0.4238 | 0.044* | |
H16 | 0.5533 | 0.2820 | 0.6061 | 0.041* | |
H17 | 0.8466 | 0.3446 | 0.5861 | 0.045* | |
H18 | 0.8908 | 0.4130 | 0.4304 | 0.042* | |
H19 | 0.6414 | 0.4124 | 0.2913 | 0.034* | |
H231 | 0.3371 | 0.7266 | −0.0972 | 0.042* | |
H24 | 0.4355 | 1.0232 | 0.1157 | 0.038* | |
H25 | 0.3642 | 1.0621 | 0.2993 | 0.041* | |
H26 | 0.2196 | 0.8977 | 0.3465 | 0.039* | |
H27 | 0.1690 | 0.6937 | 0.2161 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0292 (7) | 0.0205 (6) | 0.0225 (6) | −0.0001 (5) | 0.0026 (5) | 0.0107 (5) |
C2 | 0.0216 (7) | 0.0255 (8) | 0.0244 (7) | 0.0003 (6) | 0.0016 (5) | 0.0139 (6) |
S3 | 0.0323 (2) | 0.0242 (2) | 0.0234 (2) | 0.00018 (16) | 0.00556 (15) | 0.01144 (16) |
C4 | 0.0389 (9) | 0.0312 (9) | 0.0274 (8) | 0.0008 (7) | 0.0066 (7) | 0.0108 (7) |
C4A | 0.0270 (8) | 0.0255 (8) | 0.0277 (8) | 0.0000 (6) | 0.0031 (6) | 0.0111 (6) |
C5 | 0.0436 (10) | 0.0281 (9) | 0.0283 (9) | 0.0004 (7) | 0.0049 (7) | 0.0037 (7) |
C6 | 0.0379 (9) | 0.0237 (8) | 0.0359 (9) | −0.0008 (7) | 0.0032 (7) | 0.0099 (7) |
C7 | 0.0319 (8) | 0.0267 (8) | 0.0290 (8) | −0.0009 (6) | 0.0018 (6) | 0.0127 (7) |
C7A | 0.0244 (8) | 0.0258 (8) | 0.0249 (8) | 0.0003 (6) | −0.0001 (6) | 0.0090 (6) |
C8 | 0.0333 (8) | 0.0250 (8) | 0.0242 (8) | 0.0007 (6) | 0.0034 (6) | 0.0144 (6) |
C9 | 0.0275 (8) | 0.0266 (8) | 0.0226 (7) | 0.0017 (6) | 0.0035 (6) | 0.0126 (6) |
C10 | 0.0281 (8) | 0.0245 (8) | 0.0234 (8) | 0.0005 (6) | 0.0040 (6) | 0.0114 (6) |
C11 | 0.0234 (7) | 0.0223 (8) | 0.0233 (7) | 0.0003 (6) | 0.0024 (5) | 0.0108 (6) |
C12 | 0.0293 (8) | 0.0217 (8) | 0.0250 (8) | 0.0009 (6) | 0.0051 (6) | 0.0109 (6) |
O13 | 0.0294 (6) | 0.0454 (7) | 0.0316 (6) | 0.0012 (5) | 0.0066 (5) | 0.0206 (5) |
C14 | 0.0324 (8) | 0.0184 (7) | 0.0224 (7) | 0.0032 (6) | 0.0038 (6) | 0.0081 (6) |
C15 | 0.0382 (9) | 0.0203 (8) | 0.0245 (8) | 0.0018 (6) | 0.0047 (6) | 0.0074 (6) |
O15 | 0.0409 (7) | 0.0437 (7) | 0.0307 (6) | −0.0027 (5) | 0.0068 (5) | 0.0216 (6) |
C16 | 0.0499 (10) | 0.0316 (9) | 0.0225 (8) | 0.0090 (8) | 0.0022 (7) | 0.0114 (7) |
C17 | 0.0429 (10) | 0.0362 (10) | 0.0273 (9) | 0.0127 (8) | −0.0034 (7) | 0.0059 (7) |
C18 | 0.0310 (9) | 0.0351 (9) | 0.0305 (9) | 0.0049 (7) | 0.0028 (7) | 0.0025 (7) |
C19 | 0.0326 (8) | 0.0267 (8) | 0.0238 (8) | 0.0031 (6) | 0.0054 (6) | 0.0065 (6) |
C21 | 0.0209 (7) | 0.0261 (8) | 0.0249 (7) | 0.0016 (6) | 0.0032 (5) | 0.0127 (6) |
C22 | 0.0212 (7) | 0.0247 (8) | 0.0283 (8) | 0.0033 (6) | 0.0039 (6) | 0.0132 (6) |
O22 | 0.0381 (6) | 0.0266 (6) | 0.0246 (6) | 0.0017 (5) | 0.0071 (4) | 0.0141 (5) |
C23 | 0.0268 (8) | 0.0281 (8) | 0.0329 (8) | 0.0055 (6) | 0.0077 (6) | 0.0170 (7) |
O23 | 0.0509 (7) | 0.0264 (6) | 0.0372 (7) | 0.0049 (5) | 0.0191 (5) | 0.0180 (5) |
C24 | 0.0326 (9) | 0.0225 (8) | 0.0446 (10) | 0.0029 (7) | 0.0082 (7) | 0.0165 (7) |
C25 | 0.0388 (9) | 0.0243 (9) | 0.0378 (9) | 0.0057 (7) | 0.0039 (7) | 0.0080 (7) |
C26 | 0.0403 (9) | 0.0302 (9) | 0.0284 (8) | 0.0075 (7) | 0.0075 (7) | 0.0095 (7) |
C27 | 0.0287 (8) | 0.0260 (8) | 0.0303 (8) | 0.0035 (6) | 0.0061 (6) | 0.0138 (7) |
N1—C2 | 1.359 (2) | C12—C14 | 1.466 (2) |
N1—C7A | 1.395 (2) | C14—C19 | 1.402 (2) |
N1—C8 | 1.4617 (18) | C14—C15 | 1.413 (2) |
C2—C11 | 1.405 (2) | C15—O15 | 1.3487 (19) |
C2—S3 | 1.7485 (15) | C15—C16 | 1.390 (2) |
S3—C4A | 1.7551 (17) | O15—H151 | 0.9293 |
C4—C5 | 1.385 (2) | C16—C17 | 1.383 (3) |
C4—C4A | 1.388 (2) | C16—H16 | 0.9500 |
C4—H4 | 0.9500 | C17—C18 | 1.390 (3) |
C4A—C7A | 1.393 (2) | C17—H17 | 0.9500 |
C5—C6 | 1.394 (2) | C18—C19 | 1.376 (2) |
C5—H5 | 0.9500 | C18—H18 | 0.9500 |
C6—C7 | 1.378 (2) | C19—H19 | 0.9500 |
C6—H6 | 0.9500 | C21—O22 | 1.2817 (18) |
C7—C7A | 1.389 (2) | C21—C22 | 1.492 (2) |
C7—H7 | 0.9500 | C22—C27 | 1.402 (2) |
C8—C9 | 1.522 (2) | C22—C23 | 1.417 (2) |
C8—H8A | 0.9900 | C23—O23 | 1.3596 (19) |
C8—H8B | 0.9900 | C23—C24 | 1.388 (2) |
C9—C12 | 1.519 (2) | O23—H231 | 1.0269 |
C9—C10 | 1.528 (2) | C24—C25 | 1.378 (2) |
C9—H9 | 1.0000 | C24—H24 | 0.9500 |
C10—C11 | 1.514 (2) | C25—C26 | 1.389 (2) |
C10—H10A | 0.9900 | C25—H25 | 0.9500 |
C10—H10B | 0.9900 | C26—C27 | 1.381 (2) |
C11—C21 | 1.419 (2) | C26—H26 | 0.9500 |
C12—O13 | 1.2367 (18) | C27—H27 | 0.9500 |
C2—N1—C7A | 115.44 (12) | C21—C11—C10 | 125.28 (14) |
C2—N1—C8 | 121.75 (13) | O13—C12—C14 | 120.88 (14) |
C7A—N1—C8 | 122.78 (12) | O13—C12—C9 | 117.73 (13) |
N1—C2—C11 | 122.94 (13) | C14—C12—C9 | 121.34 (13) |
N1—C2—S3 | 110.78 (11) | C19—C14—C15 | 118.16 (14) |
C11—C2—S3 | 126.28 (12) | C19—C14—C12 | 122.58 (14) |
C2—S3—C4A | 90.82 (8) | C15—C14—C12 | 119.26 (14) |
C5—C4—C4A | 118.42 (16) | O15—C15—C16 | 117.44 (14) |
C5—C4—H4 | 120.8 | O15—C15—C14 | 122.32 (14) |
C4A—C4—H4 | 120.8 | C16—C15—C14 | 120.24 (15) |
C4—C4A—C7A | 120.46 (15) | C15—O15—H151 | 109.5 |
C4—C4A—S3 | 128.26 (13) | C17—C16—C15 | 119.88 (16) |
C7A—C4A—S3 | 111.25 (12) | C17—C16—H16 | 120.1 |
C4—C5—C6 | 120.74 (16) | C15—C16—H16 | 120.1 |
C4—C5—H5 | 119.6 | C16—C17—C18 | 120.74 (16) |
C6—C5—H5 | 119.6 | C16—C17—H17 | 119.6 |
C7—C6—C5 | 121.17 (16) | C18—C17—H17 | 119.6 |
C7—C6—H6 | 119.4 | C19—C18—C17 | 119.53 (16) |
C5—C6—H6 | 119.4 | C19—C18—H18 | 120.2 |
C6—C7—C7A | 118.04 (15) | C17—C18—H18 | 120.2 |
C6—C7—H7 | 121.0 | C18—C19—C14 | 121.37 (15) |
C7A—C7—H7 | 121.0 | C18—C19—H19 | 119.3 |
C7—C7A—C4A | 121.16 (15) | C14—C19—H19 | 119.3 |
C7—C7A—N1 | 127.14 (14) | O22—C21—C11 | 118.72 (14) |
C4A—C7A—N1 | 111.69 (14) | O22—C21—C22 | 116.56 (13) |
N1—C8—C9 | 108.08 (12) | C11—C21—C22 | 124.71 (14) |
N1—C8—H8A | 110.1 | C27—C22—C23 | 116.33 (15) |
C9—C8—H8A | 110.1 | C27—C22—C21 | 124.81 (14) |
N1—C8—H8B | 110.1 | C23—C22—C21 | 118.86 (14) |
C9—C8—H8B | 110.1 | O23—C23—C24 | 116.97 (14) |
H8A—C8—H8B | 108.4 | O23—C23—C22 | 121.86 (15) |
C12—C9—C8 | 108.14 (12) | C24—C23—C22 | 121.18 (15) |
C12—C9—C10 | 110.98 (13) | C23—O23—H231 | 103.8 |
C8—C9—C10 | 109.78 (12) | C25—C24—C23 | 120.31 (15) |
C12—C9—H9 | 109.3 | C25—C24—H24 | 119.8 |
C8—C9—H9 | 109.3 | C23—C24—H24 | 119.8 |
C10—C9—H9 | 109.3 | C24—C25—C26 | 119.94 (16) |
C11—C10—C9 | 111.33 (13) | C24—C25—H25 | 120.0 |
C11—C10—H10A | 109.4 | C26—C25—H25 | 120.0 |
C9—C10—H10A | 109.4 | C27—C26—C25 | 119.70 (16) |
C11—C10—H10B | 109.4 | C27—C26—H26 | 120.1 |
C9—C10—H10B | 109.4 | C25—C26—H26 | 120.1 |
H10A—C10—H10B | 108.0 | C26—C27—C22 | 122.26 (15) |
C2—C11—C21 | 117.09 (14) | C26—C27—H27 | 118.9 |
C2—C11—C10 | 117.58 (13) | C22—C27—H27 | 118.9 |
C7A—N1—C2—C11 | 179.53 (13) | C8—C9—C12—C14 | 126.66 (15) |
C8—N1—C2—C11 | 1.7 (2) | C10—C9—C12—C14 | −112.88 (16) |
C7A—N1—C2—S3 | −0.79 (16) | O13—C12—C14—C19 | −171.61 (15) |
C8—N1—C2—S3 | −178.60 (11) | C9—C12—C14—C19 | 11.0 (2) |
N1—C2—S3—C4A | 0.27 (11) | O13—C12—C14—C15 | 9.3 (2) |
C11—C2—S3—C4A | 179.95 (14) | C9—C12—C14—C15 | −168.11 (13) |
C5—C4—C4A—C7A | −0.4 (2) | C19—C14—C15—O15 | 178.36 (14) |
C5—C4—C4A—S3 | −178.15 (13) | C12—C14—C15—O15 | −2.5 (2) |
C2—S3—C4A—C4 | 178.21 (15) | C19—C14—C15—C16 | −3.0 (2) |
C2—S3—C4A—C7A | 0.28 (12) | C12—C14—C15—C16 | 176.10 (14) |
C4A—C4—C5—C6 | 0.3 (3) | O15—C15—C16—C17 | −178.33 (15) |
C4—C5—C6—C7 | 0.2 (3) | C14—C15—C16—C17 | 3.0 (2) |
C5—C6—C7—C7A | −0.5 (2) | C15—C16—C17—C18 | −0.8 (3) |
C6—C7—C7A—C4A | 0.4 (2) | C16—C17—C18—C19 | −1.3 (3) |
C6—C7—C7A—N1 | 179.14 (14) | C17—C18—C19—C14 | 1.2 (2) |
C4—C4A—C7A—C7 | 0.0 (2) | C15—C14—C19—C18 | 0.9 (2) |
S3—C4A—C7A—C7 | 178.13 (12) | C12—C14—C19—C18 | −178.19 (15) |
C4—C4A—C7A—N1 | −178.87 (14) | C2—C11—C21—O22 | −0.2 (2) |
S3—C4A—C7A—N1 | −0.76 (16) | C10—C11—C21—O22 | 177.32 (13) |
C2—N1—C7A—C7 | −177.80 (14) | C2—C11—C21—C22 | −178.54 (13) |
C8—N1—C7A—C7 | 0.0 (2) | C10—C11—C21—C22 | −1.0 (2) |
C2—N1—C7A—C4A | 1.01 (18) | O22—C21—C22—C27 | 161.07 (14) |
C8—N1—C7A—C4A | 178.80 (13) | C11—C21—C22—C27 | −20.5 (2) |
C2—N1—C8—C9 | −34.14 (19) | O22—C21—C22—C23 | −18.2 (2) |
C7A—N1—C8—C9 | 148.21 (14) | C11—C21—C22—C23 | 160.22 (14) |
N1—C8—C9—C12 | −179.83 (12) | C27—C22—C23—O23 | −174.36 (14) |
N1—C8—C9—C10 | 58.95 (16) | C21—C22—C23—O23 | 4.9 (2) |
C12—C9—C10—C11 | −173.14 (12) | C27—C22—C23—C24 | 6.1 (2) |
C8—C9—C10—C11 | −53.65 (16) | C21—C22—C23—C24 | −174.59 (14) |
N1—C2—C11—C21 | −177.05 (13) | O23—C23—C24—C25 | 177.01 (14) |
S3—C2—C11—C21 | 3.3 (2) | C22—C23—C24—C25 | −3.4 (2) |
N1—C2—C11—C10 | 5.2 (2) | C23—C24—C25—C26 | −1.3 (3) |
S3—C2—C11—C10 | −174.40 (11) | C24—C25—C26—C27 | 3.1 (3) |
C9—C10—C11—C2 | 21.52 (18) | C25—C26—C27—C22 | −0.2 (3) |
C9—C10—C11—C21 | −155.98 (14) | C23—C22—C27—C26 | −4.3 (2) |
C8—C9—C12—O13 | −50.82 (19) | C21—C22—C27—C26 | 176.42 (14) |
C10—C9—C12—O13 | 69.65 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H151···O13 | 0.93 | 1.74 | 2.5527 (18) | 144 |
O23—H231···O22 | 1.03 | 1.54 | 2.4919 (18) | 152 |
C4—H4···O15i | 0.95 | 2.46 | 3.345 (2) | 154 |
C9—H9···O22ii | 1.00 | 2.53 | 3.498 (2) | 162 |
C19—H19···O22ii | 0.95 | 2.51 | 3.415 (2) | 159 |
C24—H24···O23iii | 0.95 | 2.53 | 3.474 (2) | 171 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C25H19NO4S |
Mr | 429.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 7.4978 (15), 11.265 (2), 12.322 (3) |
α, β, γ (°) | 108.12 (3), 99.38 (3), 94.75 (3) |
V (Å3) | 966.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.22 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Kappa-CCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995 & 1997) |
Tmin, Tmax | 0.956, 0.970 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14805, 4393, 3506 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.111, 1.05 |
No. of reflections | 4393 |
No. of parameters | 280 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.33 |
Computer programs: Kappa-CCD Server Software (Nonius, 1997), DENZO (Otwinowski & Minor, 1997), DENZO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2000), SHELXL97 and WORDPERFECT macro PRPKAPPA (Ferguson, 1999).
N1—C2 | 1.359 (2) | S3—C4A | 1.7551 (17) |
C2—C11 | 1.405 (2) | C11—C21 | 1.419 (2) |
C2—S3 | 1.7485 (15) | C21—O22 | 1.2817 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O15—H151···O13 | 0.93 | 1.74 | 2.5527 (18) | 143.8 |
O23—H231···O22 | 1.03 | 1.54 | 2.4919 (18) | 151.8 |
C4—H4···O15i | 0.95 | 2.46 | 3.345 (2) | 154.4 |
C9—H9···O22ii | 1.00 | 2.53 | 3.498 (2) | 162.1 |
C19—H19···O22ii | 0.95 | 2.51 | 3.415 (2) | 159.1 |
C24—H24···O23iii | 0.95 | 2.53 | 3.474 (2) | 171.2 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z; (iii) −x+1, −y+2, −z. |
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Recently we reported the formation of an unexpected product, 1,3,4-thiadiazolo[3,2-a]pyridine, produced by cyclocondensation of 2-amino-1,3,4-thiadiazole with two molecules of dimethylaminopropiophenone and elimination of ammonia (Quiroga, 1998). The title compound, C25H19NO4S, (IV), was obtained by a similar cyclocondensation reaction from 2-aminobenzothiazole, the reaction mechanism is shown in the schematic diagram. \sch
Two intramolecular strong hydrogen bonds are formed at the two 2-carbonylhydroxyphenyl residues, one with O15 as the donor atom and O13 as the acceptor, 2.5527 (18) Å and the other with O23 as the donor and O22 as the acceptor, 2.4919 (18) Å. Both of these have a primary S(6) motif. The latter shorter interaction occurs because of the higher nucleophilic character of oxygen, O22, resulting from the delocalization of the lone pair on N1 of the thiazole ring with the carbonyl group at C21, the observed bond distances N1–C2 1.359 (2), C2–C11 1.405 (2), C11–C21 1.419 (2) and C21–O22 1.2817 (18) support this view.
The benzene ring in the benzothiazole moiety has the bonds and angles expected for an isolated aromatic ring, with all its bonds distances varying between 1.378 (2) and 1.394 (2) Å. These π systems are inclined at 1.48 (5)° to one another. The angle between the mean plane of the phenyl group defined by atoms C22 through C27 to that of the benzothiazole moiety is 16.77 (2)°. Selected bond lengths are given in Table 1.
The conformation of the ring, N1–C2–C11–C10–C9–C8, is an envelope with a slight skew boat contribution [puckering parameter: amplitude, Q = 0.509 (2) Å, τ = 124.3 (2)° and ϕ = 70.0 (2)°] (Boeyens, 1978), with C9 above the mean plane formed by the other atoms. The phenyl ring attached to C9 through C12 makes a nearly orthogonal angle to the mean plane of the molecule, the angle between the latter ring and benzothiazole mean planes is around 81.01 (5)°, giving the molecule a shape similar to that of a scorpion with the latter phenyl ring the tail.
In addition the molecules in (IV) are linked together into a three-dimensional framework by means of C–H···O weak hydrogen bonds. Atom C4 acts as a donor and atom O15 (x, y, −1 + z), 3.345 (2) Å, which acts as an acceptor forming a C(11) motif which forms, by translation, an infinite chain which runs parallel to [001]. A second motif involves O22 (1 − x, 1 − y, z) as an acceptor atom with both C9, 3.498 (2) Å, and C19, 3.415 (2) Å, as donor atoms, thus giving rise to an R12(7) ring. This motif is repeated by the centre at (1/2, 1/2, 0) so forming a variety of further ring motifs which can be seen in Figure 2. Finally atom C24 acts as a donor to atom O23 (1 − x, 2 − y, z), 3.474 (2) Å, so forming an R22(8) motif centred at (1/2, 1. 0). Full details ofn the hydrogen bonding are given in Table 2. Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent accessible voids in the crystal lattice.