Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001702/na6045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001702/na6045Isup2.hkl |
CCDC reference: 159763
A solution of 5-amino-3-phenylpyrazole (1 mmol) and dimedone (1 mmol) in 15 ml of absolute ethanol was heated to reflux for 25 min. The title compound appeared as a solid which was filtered off and washed with ethanol, dried and recrystallized from ethanol affording yellow crystals suitable for X-ray diffraction; yield 80%.
H atoms were treated as riding atoms with C—H distances in the range 0.95–0.99 Å and an N—H distance of 0.88 Å. No attempt was made to determine the absolute configuration since the structure contains only C, H, N and O atoms. Friedel pairs were merged. The high Rint value is due to slight interference from one or more small crystalites that it was not possible to remove from the main crystal.
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).
C17H19N3O | Dx = 1.230 Mg m−3 |
Mr = 281.35 | Melting point: 502 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
a = 19.0427 (2) Å | Cell parameters from 2770 reflections |
b = 9.6024 (4) Å | θ = 2.1–25.0° |
c = 16.6135 (7) Å | µ = 0.08 mm−1 |
V = 3037.87 (18) Å3 | T = 150 K |
Z = 8 | Plate, colourless |
F(000) = 1200 | 0.38 × 0.18 × 0.08 mm |
KappaCCD diffractometer | 3597 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.112 |
ϕ and ω scans with κ offsets | θmax = 27.5°, θmin = 2.1° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −24→24 |
Tmin = 0.971, Tmax = 0.994 | k = −11→12 |
19777 measured reflections | l = −20→21 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0707P)2] where P = (Fo2 + 2Fc2)/3 |
3597 reflections | (Δ/σ)max = 0.010 |
383 parameters | Δρmax = 0.28 e Å−3 |
1 restraint | Δρmin = −0.25 e Å−3 |
C17H19N3O | V = 3037.87 (18) Å3 |
Mr = 281.35 | Z = 8 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 19.0427 (2) Å | µ = 0.08 mm−1 |
b = 9.6024 (4) Å | T = 150 K |
c = 16.6135 (7) Å | 0.38 × 0.18 × 0.08 mm |
KappaCCD diffractometer | 3597 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 2776 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.994 | Rint = 0.112 |
19777 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 1 restraint |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.28 e Å−3 |
3597 reflections | Δρmin = −0.25 e Å−3 |
383 parameters |
Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file. |
x | y | z | Uiso*/Ueq | ||
O11 | 0.43205 (11) | 0.9588 (2) | 0.35740 (13) | 0.0273 (5) | |
C11 | 0.39797 (16) | 0.8887 (3) | 0.40828 (17) | 0.0232 (6) | |
C12 | 0.40734 (16) | 0.7438 (3) | 0.41596 (18) | 0.0226 (6) | |
C13 | 0.37079 (16) | 0.6666 (3) | 0.47159 (18) | 0.0218 (6) | |
N131 | 0.37156 (13) | 0.5258 (2) | 0.47312 (15) | 0.0241 (5) | |
C131 | 0.39220 (15) | 0.4387 (3) | 0.40949 (17) | 0.0209 (6) | |
N132 | 0.40434 (13) | 0.3058 (2) | 0.42599 (15) | 0.0220 (5) | |
N133 | 0.41568 (13) | 0.2471 (2) | 0.35219 (15) | 0.0226 (6) | |
C134 | 0.41072 (16) | 0.3413 (3) | 0.29241 (18) | 0.0220 (6) | |
C135 | 0.39547 (16) | 0.4671 (3) | 0.32706 (19) | 0.0267 (7) | |
C136 | 0.41849 (17) | 0.3049 (3) | 0.20609 (19) | 0.0251 (7) | |
C137 | 0.4437 (2) | 0.4051 (3) | 0.1532 (2) | 0.0359 (8) | |
C138 | 0.4502 (2) | 0.3747 (4) | 0.0724 (2) | 0.0390 (8) | |
C139 | 0.43195 (19) | 0.2459 (4) | 0.0441 (2) | 0.0351 (8) | |
C140 | 0.40623 (19) | 0.1452 (4) | 0.0958 (2) | 0.0359 (8) | |
C141 | 0.39987 (18) | 0.1756 (3) | 0.1777 (2) | 0.0304 (7) | |
C14 | 0.32420 (16) | 0.7331 (3) | 0.53332 (18) | 0.0244 (7) | |
C15 | 0.33307 (16) | 0.8909 (3) | 0.54219 (18) | 0.0255 (7) | |
C151 | 0.39773 (19) | 0.9228 (4) | 0.5944 (2) | 0.0366 (8) | |
C152 | 0.26719 (19) | 0.9511 (4) | 0.5812 (2) | 0.0391 (8) | |
C16 | 0.34300 (17) | 0.9583 (3) | 0.45944 (18) | 0.0265 (7) | |
O21 | 0.69341 (10) | 0.6159 (2) | 0.10657 (12) | 0.0266 (5) | |
C21 | 0.66100 (15) | 0.6801 (3) | 0.16107 (17) | 0.0219 (6) | |
C22 | 0.58770 (15) | 0.6998 (3) | 0.15888 (19) | 0.0229 (6) | |
C23 | 0.55399 (15) | 0.7785 (3) | 0.21568 (18) | 0.0209 (6) | |
N231 | 0.48568 (13) | 0.8134 (2) | 0.21422 (15) | 0.0232 (5) | |
N232 | 0.37032 (13) | 0.8184 (3) | 0.16981 (15) | 0.0244 (5) | |
N233 | 0.33641 (13) | 0.8079 (3) | 0.09820 (15) | 0.0254 (6) | |
C231 | 0.43769 (15) | 0.7993 (3) | 0.15071 (18) | 0.0218 (6) | |
C24 | 0.59347 (16) | 0.8389 (3) | 0.28614 (19) | 0.0247 (7) | |
C25 | 0.66017 (16) | 0.7600 (3) | 0.30760 (19) | 0.0260 (7) | |
C251 | 0.6420 (2) | 0.6184 (3) | 0.3448 (2) | 0.0377 (8) | |
C252 | 0.70371 (18) | 0.8460 (4) | 0.3665 (2) | 0.0364 (8) | |
C26 | 0.70245 (18) | 0.7395 (4) | 0.23038 (19) | 0.0305 (7) | |
C235 | 0.44743 (16) | 0.7757 (3) | 0.06796 (18) | 0.0236 (7) | |
C234 | 0.38061 (15) | 0.7818 (3) | 0.03598 (19) | 0.0230 (6) | |
C236 | 0.35724 (17) | 0.7682 (3) | −0.04747 (18) | 0.0239 (7) | |
C237 | 0.40750 (18) | 0.7598 (4) | −0.1087 (2) | 0.0327 (8) | |
C238 | 0.38757 (19) | 0.7458 (4) | −0.1882 (2) | 0.0351 (8) | |
C239 | 0.31734 (19) | 0.7380 (3) | −0.2083 (2) | 0.0327 (8) | |
C240 | 0.26703 (17) | 0.7467 (3) | −0.1487 (2) | 0.0323 (7) | |
C241 | 0.28650 (17) | 0.7621 (3) | −0.06840 (19) | 0.0277 (7) | |
H12 | 0.4399 | 0.6980 | 0.3816 | 0.027* | |
H131 | 0.3579 | 0.4852 | 0.5180 | 0.029* | |
H133 | 0.4251 | 0.1583 | 0.3446 | 0.027* | |
H135 | 0.3886 | 0.5540 | 0.3010 | 0.032* | |
H137 | 0.4564 | 0.4947 | 0.1727 | 0.043* | |
H138 | 0.4674 | 0.4434 | 0.0362 | 0.047* | |
H139 | 0.4370 | 0.2254 | −0.0115 | 0.042* | |
H140 | 0.3930 | 0.0563 | 0.0758 | 0.043* | |
H141 | 0.3827 | 0.1068 | 0.2138 | 0.037* | |
H14B | 0.3335 | 0.6891 | 0.5861 | 0.029* | |
H14D | 0.2747 | 0.7133 | 0.5191 | 0.029* | |
H15E | 0.4060 | 1.0235 | 0.5953 | 0.055* | |
H15F | 0.4389 | 0.8756 | 0.5719 | 0.055* | |
H15G | 0.3895 | 0.8896 | 0.6494 | 0.055* | |
H15H | 0.2715 | 1.0526 | 0.5847 | 0.059* | |
H15I | 0.2617 | 0.9121 | 0.6353 | 0.059* | |
H15J | 0.2261 | 0.9272 | 0.5485 | 0.059* | |
H16A | 0.2976 | 0.9562 | 0.4303 | 0.032* | |
H16B | 0.3562 | 1.0572 | 0.4671 | 0.032* | |
H22 | 0.5611 | 0.6575 | 0.1171 | 0.027* | |
H231 | 0.4689 | 0.8499 | 0.2589 | 0.028* | |
H233 | 0.2907 | 0.8171 | 0.0927 | 0.031* | |
H24C | 0.5621 | 0.8398 | 0.3337 | 0.030* | |
H24D | 0.6059 | 0.9366 | 0.2736 | 0.030* | |
H25B | 0.6854 | 0.5676 | 0.3567 | 0.056* | |
H25F | 0.6136 | 0.5645 | 0.3067 | 0.056* | |
H25G | 0.6155 | 0.6326 | 0.3946 | 0.056* | |
H25H | 0.6780 | 0.8560 | 0.4173 | 0.055* | |
H25I | 0.7126 | 0.9383 | 0.3435 | 0.055* | |
H25J | 0.7485 | 0.7989 | 0.3767 | 0.055* | |
H26A | 0.7221 | 0.8306 | 0.2138 | 0.037* | |
H26B | 0.7424 | 0.6767 | 0.2420 | 0.037* | |
H235 | 0.4903 | 0.7593 | 0.0403 | 0.028* | |
H237 | 0.4560 | 0.7638 | −0.0954 | 0.039* | |
H238 | 0.4223 | 0.7415 | −0.2291 | 0.042* | |
H239 | 0.3037 | 0.7267 | −0.2629 | 0.039* | |
H240 | 0.2187 | 0.7423 | −0.1626 | 0.039* | |
H241 | 0.2515 | 0.7684 | −0.0278 | 0.033* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O11 | 0.0321 (12) | 0.0237 (10) | 0.0261 (11) | −0.0025 (9) | 0.0069 (9) | 0.0007 (9) |
C11 | 0.0300 (17) | 0.0257 (15) | 0.0140 (14) | −0.0001 (13) | −0.0024 (12) | −0.0019 (11) |
C12 | 0.0253 (16) | 0.0248 (15) | 0.0176 (15) | 0.0024 (12) | 0.0024 (12) | −0.0020 (11) |
C13 | 0.0254 (16) | 0.0251 (15) | 0.0148 (13) | 0.0026 (13) | −0.0022 (12) | −0.0003 (11) |
N131 | 0.0323 (15) | 0.0258 (13) | 0.0143 (11) | −0.0005 (11) | 0.0031 (11) | 0.0001 (10) |
C131 | 0.0228 (15) | 0.0203 (14) | 0.0197 (15) | −0.0008 (11) | −0.0019 (11) | 0.0002 (12) |
N132 | 0.0200 (13) | 0.0234 (12) | 0.0225 (13) | 0.0008 (10) | 0.0002 (10) | −0.0027 (11) |
N133 | 0.0251 (14) | 0.0222 (13) | 0.0205 (13) | 0.0012 (10) | 0.0011 (11) | −0.0028 (10) |
C134 | 0.0220 (16) | 0.0232 (15) | 0.0209 (15) | −0.0020 (12) | 0.0025 (12) | −0.0023 (12) |
C135 | 0.0344 (18) | 0.0221 (15) | 0.0237 (15) | −0.0006 (13) | 0.0023 (12) | 0.0012 (12) |
C136 | 0.0281 (18) | 0.0256 (15) | 0.0215 (15) | 0.0030 (13) | 0.0017 (12) | −0.0001 (12) |
C137 | 0.051 (2) | 0.0284 (17) | 0.0279 (18) | −0.0068 (15) | 0.0043 (15) | 0.0006 (14) |
C138 | 0.051 (2) | 0.041 (2) | 0.0246 (17) | −0.0066 (17) | 0.0050 (15) | 0.0056 (15) |
C139 | 0.043 (2) | 0.042 (2) | 0.0212 (16) | 0.0069 (15) | −0.0003 (15) | −0.0023 (13) |
C140 | 0.047 (2) | 0.0320 (18) | 0.0291 (18) | 0.0004 (15) | −0.0023 (15) | −0.0079 (15) |
C141 | 0.039 (2) | 0.0263 (16) | 0.0262 (17) | 0.0002 (14) | 0.0028 (13) | −0.0030 (13) |
C14 | 0.0282 (17) | 0.0296 (16) | 0.0156 (14) | −0.0001 (13) | 0.0017 (12) | −0.0001 (12) |
C15 | 0.0298 (17) | 0.0274 (16) | 0.0194 (15) | 0.0014 (13) | 0.0030 (13) | −0.0025 (12) |
C151 | 0.048 (2) | 0.036 (2) | 0.0252 (17) | −0.0056 (15) | −0.0048 (15) | −0.0060 (14) |
C152 | 0.048 (2) | 0.0367 (18) | 0.0324 (18) | 0.0099 (16) | 0.0150 (16) | 0.0005 (15) |
C16 | 0.0313 (17) | 0.0238 (15) | 0.0244 (16) | 0.0035 (13) | 0.0055 (13) | 0.0023 (12) |
O21 | 0.0198 (11) | 0.0402 (13) | 0.0199 (10) | 0.0047 (9) | −0.0008 (8) | −0.0060 (9) |
C21 | 0.0204 (15) | 0.0270 (15) | 0.0184 (14) | 0.0004 (12) | 0.0009 (12) | 0.0003 (12) |
C22 | 0.0211 (15) | 0.0277 (15) | 0.0198 (14) | −0.0008 (13) | −0.0008 (12) | −0.0030 (12) |
C23 | 0.0182 (15) | 0.0226 (14) | 0.0220 (15) | −0.0012 (12) | 0.0007 (11) | 0.0028 (12) |
N231 | 0.0219 (13) | 0.0290 (13) | 0.0187 (12) | 0.0021 (10) | 0.0002 (10) | −0.0037 (10) |
N232 | 0.0179 (13) | 0.0326 (13) | 0.0225 (13) | −0.0004 (11) | −0.0008 (10) | 0.0006 (11) |
N233 | 0.0160 (13) | 0.0377 (15) | 0.0226 (13) | −0.0023 (11) | 0.0013 (10) | −0.0013 (11) |
C231 | 0.0197 (16) | 0.0252 (14) | 0.0205 (15) | −0.0003 (12) | −0.0009 (12) | −0.0010 (12) |
C24 | 0.0244 (16) | 0.0288 (16) | 0.0208 (15) | −0.0004 (12) | −0.0009 (12) | −0.0052 (12) |
C25 | 0.0254 (17) | 0.0331 (17) | 0.0195 (16) | 0.0045 (13) | −0.0018 (12) | −0.0028 (12) |
C251 | 0.049 (2) | 0.0369 (19) | 0.0267 (17) | 0.0098 (16) | −0.0016 (16) | 0.0052 (14) |
C252 | 0.0316 (19) | 0.051 (2) | 0.0262 (17) | 0.0056 (15) | −0.0068 (14) | −0.0105 (15) |
C26 | 0.0231 (17) | 0.0470 (19) | 0.0215 (17) | 0.0029 (14) | −0.0026 (13) | −0.0016 (13) |
C235 | 0.0175 (15) | 0.0289 (16) | 0.0245 (16) | 0.0014 (12) | 0.0012 (12) | −0.0015 (12) |
C234 | 0.0184 (16) | 0.0247 (15) | 0.0258 (16) | 0.0002 (12) | 0.0006 (13) | −0.0018 (13) |
C236 | 0.0215 (16) | 0.0271 (15) | 0.0232 (16) | −0.0003 (12) | −0.0021 (12) | 0.0014 (12) |
C237 | 0.0202 (17) | 0.053 (2) | 0.0250 (17) | −0.0031 (14) | 0.0007 (14) | 0.0004 (14) |
C238 | 0.0292 (19) | 0.052 (2) | 0.0238 (17) | 0.0026 (16) | 0.0037 (14) | 0.0000 (15) |
C239 | 0.037 (2) | 0.0409 (19) | 0.0204 (16) | −0.0004 (15) | −0.0036 (14) | 0.0014 (14) |
C240 | 0.0218 (17) | 0.0445 (19) | 0.0307 (18) | −0.0019 (14) | −0.0052 (14) | 0.0034 (15) |
C241 | 0.0222 (16) | 0.0350 (17) | 0.0260 (16) | 0.0006 (13) | −0.0020 (13) | 0.0025 (13) |
O11—C11 | 1.260 (4) | O21—C21 | 1.257 (3) |
C11—C12 | 1.409 (4) | C21—C22 | 1.409 (4) |
C11—C16 | 1.505 (4) | C21—C26 | 1.508 (4) |
C12—C13 | 1.374 (4) | C22—C23 | 1.369 (4) |
C12—H12 | 0.9500 | C22—H22 | 0.9500 |
C13—N131 | 1.353 (4) | C23—N231 | 1.344 (4) |
C13—C14 | 1.499 (4) | C23—C24 | 1.507 (4) |
N131—C131 | 1.404 (4) | N231—C231 | 1.402 (4) |
N131—H131 | 0.8800 | N231—H231 | 0.8800 |
C131—N132 | 1.325 (4) | N232—C231 | 1.334 (4) |
C131—C135 | 1.398 (4) | N232—N233 | 1.357 (3) |
N132—N133 | 1.367 (4) | N233—C234 | 1.356 (4) |
N133—C134 | 1.347 (4) | N233—H233 | 0.8800 |
N133—H133 | 0.8800 | C231—C235 | 1.405 (4) |
C134—C135 | 1.369 (4) | C24—C25 | 1.521 (4) |
C134—C136 | 1.483 (4) | C24—H24C | 0.9900 |
C135—H135 | 0.9500 | C24—H24D | 0.9900 |
C136—C141 | 1.375 (5) | C25—C252 | 1.526 (4) |
C136—C137 | 1.389 (5) | C25—C251 | 1.532 (5) |
C137—C138 | 1.380 (5) | C25—C26 | 1.527 (5) |
C137—H137 | 0.9500 | C251—H25B | 0.9800 |
C138—C139 | 1.367 (5) | C251—H25F | 0.9800 |
C138—H138 | 0.9500 | C251—H25G | 0.9800 |
C139—C140 | 1.383 (5) | C252—H25H | 0.9800 |
C139—H139 | 0.9500 | C252—H25I | 0.9800 |
C140—C141 | 1.397 (5) | C252—H25J | 0.9800 |
C140—H140 | 0.9500 | C26—H26A | 0.9900 |
C141—H141 | 0.9500 | C26—H26B | 0.9900 |
C14—C15 | 1.531 (4) | C235—C234 | 1.380 (4) |
C14—H14B | 0.9900 | C235—H235 | 0.9500 |
C14—H14D | 0.9900 | C234—C236 | 1.462 (4) |
C15—C152 | 1.525 (4) | C236—C241 | 1.392 (4) |
C15—C16 | 1.531 (4) | C236—C237 | 1.399 (4) |
C15—C151 | 1.537 (4) | C237—C238 | 1.381 (5) |
C151—H15E | 0.9800 | C237—H237 | 0.9500 |
C151—H15F | 0.9800 | C238—C239 | 1.381 (5) |
C151—H15G | 0.9800 | C238—H238 | 0.9500 |
C152—H15H | 0.9800 | C239—C240 | 1.380 (5) |
C152—H15I | 0.9800 | C239—H239 | 0.9500 |
C152—H15J | 0.9800 | C240—C241 | 1.393 (5) |
C16—H16A | 0.9900 | C240—H240 | 0.9500 |
C16—H16B | 0.9900 | C241—H241 | 0.9500 |
O11—C11—C12 | 121.5 (3) | O21—C21—C22 | 122.3 (3) |
O11—C11—C16 | 120.0 (3) | O21—C21—C26 | 118.6 (3) |
C12—C11—C16 | 118.4 (3) | C22—C21—C26 | 119.2 (3) |
C13—C12—C11 | 122.0 (3) | C23—C22—C21 | 121.4 (3) |
C13—C12—H12 | 119.0 | C23—C22—H22 | 119.3 |
C11—C12—H12 | 119.0 | C21—C22—H22 | 119.3 |
N131—C13—C12 | 123.1 (3) | N231—C23—C22 | 125.4 (3) |
N131—C13—C14 | 114.8 (3) | N231—C23—C24 | 113.6 (3) |
C12—C13—C14 | 122.0 (3) | C22—C23—C24 | 120.9 (3) |
C13—N131—C131 | 125.8 (2) | C23—N231—C231 | 128.3 (3) |
C13—N131—H131 | 117.1 | C23—N231—H231 | 115.8 |
C131—N131—H131 | 117.1 | C231—N231—H231 | 115.8 |
N132—C131—C135 | 112.5 (3) | C231—N232—N233 | 103.8 (2) |
N132—C131—N131 | 117.8 (3) | N232—N233—C234 | 112.7 (2) |
C135—C131—N131 | 129.4 (3) | N232—N233—H233 | 123.6 |
C131—N132—N133 | 103.8 (2) | C234—N233—H233 | 123.6 |
C134—N133—N132 | 111.9 (2) | N232—C231—N231 | 115.7 (3) |
C134—N133—H133 | 124.0 | N232—C231—C235 | 112.4 (3) |
N132—N133—H133 | 124.0 | N231—C231—C235 | 131.7 (3) |
N133—C134—C135 | 107.3 (3) | C23—C24—C25 | 114.0 (3) |
N133—C134—C136 | 123.2 (3) | C23—C24—H24C | 108.8 |
C135—C134—C136 | 129.5 (3) | C25—C24—H24C | 108.8 |
C134—C135—C131 | 104.5 (3) | C23—C24—H24D | 108.8 |
C134—C135—H135 | 127.8 | C25—C24—H24D | 108.8 |
C131—C135—H135 | 127.8 | H24C—C24—H24D | 107.6 |
C141—C136—C137 | 119.9 (3) | C24—C25—C252 | 109.5 (3) |
C141—C136—C134 | 121.3 (3) | C24—C25—C251 | 110.4 (3) |
C137—C136—C134 | 118.9 (3) | C252—C25—C251 | 110.1 (3) |
C138—C137—C136 | 120.0 (3) | C24—C25—C26 | 107.9 (3) |
C138—C137—H137 | 120.0 | C252—C25—C26 | 108.8 (3) |
C136—C137—H137 | 120.0 | C251—C25—C26 | 110.1 (3) |
C139—C138—C137 | 120.2 (3) | C25—C251—H25B | 109.5 |
C139—C138—H138 | 119.9 | C25—C251—H25F | 109.5 |
C137—C138—H138 | 119.9 | H25B—C251—H25F | 109.5 |
C138—C139—C140 | 120.6 (3) | C25—C251—H25G | 109.5 |
C138—C139—H139 | 119.7 | H25B—C251—H25G | 109.5 |
C140—C139—H139 | 119.7 | H25F—C251—H25G | 109.5 |
C139—C140—C141 | 119.3 (3) | C25—C252—H25H | 109.5 |
C139—C140—H140 | 120.3 | C25—C252—H25I | 109.5 |
C141—C140—H140 | 120.3 | H25H—C252—H25I | 109.5 |
C136—C141—C140 | 120.0 (3) | C25—C252—H25J | 109.5 |
C136—C141—H141 | 120.0 | H25H—C252—H25J | 109.5 |
C140—C141—H141 | 120.0 | H25I—C252—H25J | 109.5 |
C13—C14—C15 | 115.0 (2) | C21—C26—C25 | 114.5 (3) |
C13—C14—H14B | 108.5 | C21—C26—H26A | 108.6 |
C15—C14—H14B | 108.5 | C25—C26—H26A | 108.6 |
C13—C14—H14D | 108.5 | C21—C26—H26B | 108.6 |
C15—C14—H14D | 108.5 | C25—C26—H26B | 108.6 |
H14B—C14—H14D | 107.5 | H26A—C26—H26B | 107.6 |
C152—C15—C16 | 108.8 (3) | C234—C235—C231 | 104.4 (3) |
C152—C15—C14 | 109.0 (3) | C234—C235—H235 | 127.8 |
C16—C15—C14 | 110.2 (2) | C231—C235—H235 | 127.8 |
C152—C15—C151 | 110.1 (3) | N233—C234—C235 | 106.6 (3) |
C16—C15—C151 | 108.9 (3) | N233—C234—C236 | 123.4 (3) |
C14—C15—C151 | 109.9 (3) | C235—C234—C236 | 129.9 (3) |
C15—C151—H15E | 109.5 | C241—C236—C237 | 118.6 (3) |
C15—C151—H15F | 109.5 | C241—C236—C234 | 122.4 (3) |
H15E—C151—H15F | 109.5 | C237—C236—C234 | 119.1 (3) |
C15—C151—H15G | 109.5 | C238—C237—C236 | 120.9 (3) |
H15E—C151—H15G | 109.5 | C238—C237—H237 | 119.6 |
H15F—C151—H15G | 109.5 | C236—C237—H237 | 119.6 |
C15—C152—H15H | 109.5 | C237—C238—C239 | 120.2 (3) |
C15—C152—H15I | 109.5 | C237—C238—H238 | 119.9 |
H15H—C152—H15I | 109.5 | C239—C238—H238 | 119.9 |
C15—C152—H15J | 109.5 | C240—C239—C238 | 119.7 (3) |
H15H—C152—H15J | 109.5 | C240—C239—H239 | 120.2 |
H15I—C152—H15J | 109.5 | C238—C239—H239 | 120.2 |
C11—C16—C15 | 113.9 (2) | C239—C240—C241 | 120.6 (3) |
C11—C16—H16A | 108.8 | C239—C240—H240 | 119.7 |
C15—C16—H16A | 108.8 | C241—C240—H240 | 119.7 |
C11—C16—H16B | 108.8 | C236—C241—C240 | 120.1 (3) |
C15—C16—H16B | 108.8 | C236—C241—H241 | 120.0 |
H16A—C16—H16B | 107.7 | C240—C241—H241 | 120.0 |
O11—C11—C12—C13 | 179.6 (3) | O21—C21—C22—C23 | −175.2 (3) |
C16—C11—C12—C13 | −3.8 (4) | C26—C21—C22—C23 | 3.9 (4) |
C11—C12—C13—N131 | 170.8 (3) | C21—C22—C23—N231 | 173.5 (3) |
C11—C12—C13—C14 | −6.4 (5) | C21—C22—C23—C24 | −4.3 (4) |
C12—C13—N131—C131 | −18.0 (5) | C22—C23—N231—C231 | −11.7 (5) |
C14—C13—N131—C131 | 159.4 (3) | C24—C23—N231—C231 | 166.2 (3) |
C13—N131—C131—N132 | 165.7 (3) | C231—N232—N233—C234 | 0.6 (3) |
C13—N131—C131—C135 | −21.6 (5) | N233—N232—C231—N231 | 176.3 (2) |
C135—C131—N132—N133 | 0.0 (3) | N233—N232—C231—C235 | −0.4 (3) |
N131—C131—N132—N133 | 173.8 (2) | C23—N231—C231—N232 | 168.2 (3) |
C131—N132—N133—C134 | 0.1 (3) | C23—N231—C231—C235 | −15.9 (5) |
N132—N133—C134—C135 | −0.1 (3) | N231—C23—C24—C25 | 157.6 (3) |
N132—N133—C134—C136 | −178.0 (3) | C22—C23—C24—C25 | −24.3 (4) |
N133—C134—C135—C131 | 0.1 (3) | C23—C24—C25—C252 | 167.9 (3) |
C136—C134—C135—C131 | 177.8 (3) | C23—C24—C25—C251 | −70.7 (3) |
N132—C131—C135—C134 | 0.0 (4) | C23—C24—C25—C26 | 49.6 (3) |
N131—C131—C135—C134 | −173.0 (3) | O21—C21—C26—C25 | −155.8 (3) |
N133—C134—C136—C141 | 30.0 (5) | C22—C21—C26—C25 | 25.1 (4) |
C135—C134—C136—C141 | −147.5 (3) | C24—C25—C26—C21 | −50.2 (4) |
N133—C134—C136—C137 | −151.5 (3) | C252—C25—C26—C21 | −169.0 (3) |
C135—C134—C136—C137 | 31.1 (5) | C251—C25—C26—C21 | 70.3 (3) |
C141—C136—C137—C138 | −0.2 (5) | N232—C231—C235—C234 | 0.2 (3) |
C134—C136—C137—C138 | −178.8 (3) | N231—C231—C235—C234 | −175.9 (3) |
C136—C137—C138—C139 | 0.0 (6) | N232—N233—C234—C235 | −0.5 (3) |
C137—C138—C139—C140 | 0.6 (6) | N232—N233—C234—C236 | −179.0 (3) |
C138—C139—C140—C141 | −0.9 (5) | C231—C235—C234—N233 | 0.2 (3) |
C137—C136—C141—C140 | −0.1 (5) | C231—C235—C234—C236 | 178.6 (3) |
C134—C136—C141—C140 | 178.5 (3) | N233—C234—C236—C241 | −9.0 (5) |
C139—C140—C141—C136 | 0.6 (5) | C235—C234—C236—C241 | 172.9 (3) |
N131—C13—C14—C15 | 169.4 (3) | N233—C234—C236—C237 | 171.5 (3) |
C12—C13—C14—C15 | −13.1 (4) | C235—C234—C236—C237 | −6.6 (5) |
C13—C14—C15—C152 | 159.2 (3) | C241—C236—C237—C238 | 0.0 (5) |
C13—C14—C15—C16 | 39.9 (3) | C234—C236—C237—C238 | 179.5 (3) |
C13—C14—C15—C151 | −80.1 (3) | C236—C237—C238—C239 | −0.8 (6) |
O11—C11—C16—C15 | −150.5 (3) | C237—C238—C239—C240 | 1.1 (6) |
C12—C11—C16—C15 | 32.8 (4) | C238—C239—C240—C241 | −0.6 (5) |
C152—C15—C16—C11 | −168.9 (3) | C237—C236—C241—C240 | 0.5 (5) |
C14—C15—C16—C11 | −49.5 (4) | C234—C236—C241—C240 | −179.0 (3) |
C151—C15—C16—C11 | 71.0 (3) | C239—C240—C241—C236 | −0.3 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N131—H131···O21i | 0.88 | 2.02 | 2.881 (3) | 167 |
N133—H133···O11ii | 0.88 | 1.93 | 2.788 (3) | 164 |
N233—H233···O21iii | 0.88 | 1.98 | 2.825 (3) | 162 |
N231—H231···O11 | 0.88 | 2.07 | 2.942 (4) | 173 |
C237—H237···N133iv | 0.95 | 2.59 | 3.430 (4) | 147 |
C240—H240···N133v | 0.95 | 2.57 | 3.479 (4) | 160 |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1/2, y+1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H19N3O |
Mr | 281.35 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 150 |
a, b, c (Å) | 19.0427 (2), 9.6024 (4), 16.6135 (7) |
V (Å3) | 3037.87 (18) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.38 × 0.18 × 0.08 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.971, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19777, 3597, 2776 |
Rint | 0.112 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.123, 0.99 |
No. of reflections | 3597 |
No. of parameters | 383 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.25 |
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).
C13—N131 | 1.353 (4) | N231—C231 | 1.402 (4) |
N131—C131 | 1.404 (4) | N232—C231 | 1.334 (4) |
C131—N132 | 1.325 (4) | N232—N233 | 1.357 (3) |
N132—N133 | 1.367 (4) | N233—C234 | 1.356 (4) |
N133—C134 | 1.347 (4) | ||
C13—N131—C131 | 125.8 (2) | C23—N231—C231 | 128.3 (3) |
C131—N132—N133 | 103.8 (2) | C231—N232—N233 | 103.8 (2) |
C134—N133—N132 | 111.9 (2) | N232—N233—C234 | 112.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N131—H131···O21i | 0.88 | 2.02 | 2.881 (3) | 167 |
N133—H133···O11ii | 0.88 | 1.93 | 2.788 (3) | 164 |
N233—H233···O21iii | 0.88 | 1.98 | 2.825 (3) | 162 |
N231—H231···O11 | 0.88 | 2.07 | 2.942 (4) | 173 |
C237—H237···N133iv | 0.95 | 2.59 | 3.430 (4) | 147 |
C240—H240···N133v | 0.95 | 2.57 | 3.479 (4) | 160 |
Symmetry codes: (i) −x+1, −y+1, z+1/2; (ii) x, y−1, z; (iii) x−1/2, −y+3/2, z; (iv) −x+1, −y+1, z−1/2; (v) −x+1/2, y+1/2, z−1/2. |
The title compound, (I), was an intermediate in the prepararation of pyrazolo[3,4-b]quinolin-5-ones. Geometric parameters are given in Table 1 and a view of each individual molecule is given in Fig. 1.
The primary supramolecular structures are a C(9) motif, (Bernstein et al., 1995). involving only molecule 1, N133—H133···O11ii [symmetry code: (ii) x, y - 1, z]. A similar chain perpendicular to the first is formed by molecule 2 and its symmetry-related molecules by the C(9) motif, N233—H233···O21iii [symmetry code: (iii) x - 1/2, -y + 1/2, 1 + z]. These chains are then interlinked by further hydrogen bonds, N131—H131···O21i and N231—H231···O11, which links the two molecules in the asymmetric unit [symmetry code: (i) 1 - x, 1 - y, z + 1/2]. These along with two weak C—H···N hydrogen bonds combine to form a complex three-dimensional network. The details of the hydrogen bonding is given in Table 2.
Examination of the structure with PLATON (Spek, 2000) showed that there were no solvent-accessible voids in the crystal lattice.
The high Rint value is due to slight interference from one or more small crystallites that it was not possible to remove from the main crystal.