Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801001489/na6039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801001489/na6039Isup2.hkl |
CCDC reference: 159753
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.051
- wR factor = 0.137
- Data-to-parameter ratio = 18.0
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
A solution of 5-aminopyrazole (1 mmol), dimedone, (1 mmol) and 2-naphthaldehyde (1 mmol) in 15 ml of absolute ethanol were heated to reflux for 20–50 min (thin-layer chromatography control control). The reaction mixture was cooled and the solid corresponding to the title compound was filtered out, washed with ethanol, dried and recrystallized from ethanol to afford suitable crystals for diffraction. 65% yield, m.p. 602 K).
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).
C23H23N3O | Dx = 1.236 Mg m−3 |
Mr = 357.44 | Melting point: 602 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1222 (18) Å | Cell parameters from 4401 reflections |
b = 15.281 (3) Å | θ = 2.0–27.6° |
c = 14.346 (3) Å | µ = 0.08 mm−1 |
β = 106.13 (3)° | T = 150 K |
V = 1921.0 (7) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.18 × 0.14 mm |
F(000) = 760 |
KappaCCD diffractometer | 4401 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 2994 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
ϕ and ω scans with κ offsets | θmax = 27.6°, θmin = 2.0° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.974, Tmax = 0.989 | k = −19→19 |
16205 measured reflections | l = −18→18 |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0763P)2] where P = (Fo2 + 2Fc2)/3 |
4401 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C23H23N3O | V = 1921.0 (7) Å3 |
Mr = 357.44 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 9.1222 (18) Å | µ = 0.08 mm−1 |
b = 15.281 (3) Å | T = 150 K |
c = 14.346 (3) Å | 0.35 × 0.18 × 0.14 mm |
β = 106.13 (3)° |
KappaCCD diffractometer | 4401 independent reflections |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | 2994 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.989 | Rint = 0.062 |
16205 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.23 e Å−3 |
4401 reflections | Δρmin = −0.28 e Å−3 |
245 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 | ||
N1 | −0.08690 (15) | 0.49567 (8) | 0.87092 (9) | 0.0266 (3) | |
N2 | −0.14671 (14) | 0.50100 (8) | 0.77261 (9) | 0.0271 (3) | |
C3 | −0.11695 (17) | 0.43020 (10) | 0.72492 (11) | 0.0259 (4) | |
C31 | −0.1677 (2) | 0.42393 (12) | 0.61717 (11) | 0.0358 (4) | |
C3A | −0.03500 (17) | 0.37374 (10) | 0.79488 (11) | 0.0245 (3) | |
C4 | 0.02769 (17) | 0.28315 (9) | 0.79326 (11) | 0.0236 (3) | |
C41 | −0.13242 (18) | 0.15730 (10) | 0.70697 (11) | 0.0275 (4) | |
C42 | −0.09687 (18) | 0.21414 (10) | 0.78258 (11) | 0.0250 (3) | |
C43 | −0.17867 (19) | 0.20933 (11) | 0.85316 (12) | 0.0310 (4) | |
C44 | −0.2933 (2) | 0.15026 (11) | 0.84482 (12) | 0.0338 (4) | |
C45 | −0.45556 (19) | 0.03165 (11) | 0.75382 (13) | 0.0362 (4) | |
C46 | −0.4903 (2) | −0.02461 (11) | 0.67764 (13) | 0.0407 (5) | |
C47 | −0.4042 (2) | −0.02429 (12) | 0.61067 (14) | 0.0429 (5) | |
C48 | −0.2890 (2) | 0.03424 (11) | 0.61845 (13) | 0.0368 (4) | |
C48A | −0.25077 (17) | 0.09393 (10) | 0.69594 (11) | 0.0273 (4) | |
C44A | −0.33384 (18) | 0.09171 (10) | 0.76635 (11) | 0.0300 (4) | |
C4A | 0.15391 (17) | 0.27030 (9) | 0.88723 (10) | 0.0233 (3) | |
C5 | 0.26617 (17) | 0.20408 (9) | 0.88870 (11) | 0.0240 (3) | |
O51 | 0.26432 (13) | 0.15970 (7) | 0.81623 (8) | 0.0308 (3) | |
C6 | 0.39283 (18) | 0.19092 (10) | 0.98122 (11) | 0.0274 (4) | |
C7 | 0.34492 (17) | 0.20762 (9) | 1.07350 (11) | 0.0253 (4) | |
C71 | 0.48401 (19) | 0.20359 (11) | 1.16209 (12) | 0.0330 (4) | |
C72 | 0.22789 (19) | 0.13925 (10) | 1.08329 (12) | 0.0316 (4) | |
C8 | 0.27666 (18) | 0.29944 (10) | 1.06552 (11) | 0.0264 (4) | |
C8A | 0.16174 (17) | 0.31720 (9) | 0.96983 (11) | 0.0236 (3) | |
N9 | 0.06635 (15) | 0.38529 (8) | 0.97054 (9) | 0.0262 (3) | |
C9A | −0.01999 (17) | 0.41768 (10) | 0.88167 (10) | 0.0240 (3) | |
H2 | −0.1995 | 0.5462 | 0.7433 | 0.033* | |
H31A | −0.2657 | 0.4541 | 0.5925 | 0.054* | |
H31B | −0.1795 | 0.3622 | 0.5979 | 0.054* | |
H31C | −0.0914 | 0.4513 | 0.5901 | 0.054* | |
H4 | 0.0724 | 0.2782 | 0.7372 | 0.028* | |
H41 | −0.0768 | 0.1598 | 0.6600 | 0.033* | |
H43 | −0.1531 | 0.2479 | 0.9072 | 0.037* | |
H44 | −0.3468 | 0.1486 | 0.8929 | 0.041* | |
H45 | −0.5139 | 0.0307 | 0.7993 | 0.043* | |
H46 | −0.5730 | −0.0643 | 0.6698 | 0.049* | |
H47 | −0.4265 | −0.0655 | 0.5591 | 0.051* | |
H48 | −0.2340 | 0.0348 | 0.5711 | 0.044* | |
H6A | 0.4783 | 0.2306 | 0.9806 | 0.033* | |
H6B | 0.4309 | 0.1301 | 0.9827 | 0.033* | |
H71A | 0.4522 | 0.2144 | 1.2209 | 0.049* | |
H71B | 0.5581 | 0.2482 | 1.1562 | 0.049* | |
H71C | 0.5311 | 0.1456 | 1.1660 | 0.049* | |
H72A | 0.1977 | 0.1504 | 1.1427 | 0.047* | |
H72B | 0.2730 | 0.0807 | 1.0865 | 0.047* | |
H72C | 0.1379 | 0.1428 | 1.0270 | 0.047* | |
H8A | 0.2270 | 0.3077 | 1.1181 | 0.032* | |
H8B | 0.3602 | 0.3428 | 1.0753 | 0.032* | |
H9 | 0.0594 | 0.4082 | 1.0255 | 0.031* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0290 (7) | 0.0236 (7) | 0.0251 (7) | 0.0037 (6) | 0.0042 (6) | 0.0018 (6) |
N2 | 0.0272 (7) | 0.0246 (7) | 0.0268 (7) | 0.0048 (6) | 0.0030 (6) | 0.0038 (6) |
C3 | 0.0245 (8) | 0.0269 (8) | 0.0265 (8) | −0.0006 (7) | 0.0070 (7) | 0.0026 (7) |
C31 | 0.0367 (10) | 0.0407 (10) | 0.0266 (8) | 0.0049 (8) | 0.0033 (7) | 0.0026 (8) |
C3A | 0.0241 (8) | 0.0238 (8) | 0.0251 (8) | 0.0002 (6) | 0.0063 (6) | 0.0001 (7) |
C4 | 0.0263 (8) | 0.0236 (8) | 0.0211 (7) | 0.0001 (6) | 0.0071 (6) | −0.0024 (6) |
C41 | 0.0247 (9) | 0.0287 (8) | 0.0283 (8) | 0.0041 (7) | 0.0060 (7) | −0.0029 (7) |
C42 | 0.0252 (8) | 0.0216 (8) | 0.0250 (7) | 0.0043 (6) | 0.0018 (6) | −0.0002 (6) |
C43 | 0.0341 (10) | 0.0308 (8) | 0.0272 (8) | −0.0019 (7) | 0.0068 (7) | −0.0029 (7) |
C44 | 0.0347 (10) | 0.0373 (9) | 0.0311 (9) | 0.0001 (8) | 0.0119 (7) | 0.0027 (8) |
C45 | 0.0282 (10) | 0.0323 (9) | 0.0448 (10) | −0.0007 (7) | 0.0046 (8) | 0.0083 (8) |
C46 | 0.0312 (10) | 0.0282 (9) | 0.0536 (11) | −0.0042 (8) | −0.0033 (9) | 0.0058 (9) |
C47 | 0.0374 (11) | 0.0304 (9) | 0.0509 (11) | 0.0000 (8) | −0.0044 (9) | −0.0091 (9) |
C48 | 0.0324 (10) | 0.0334 (9) | 0.0409 (10) | 0.0030 (8) | 0.0038 (8) | −0.0090 (8) |
C48A | 0.0228 (8) | 0.0229 (8) | 0.0320 (8) | 0.0048 (6) | 0.0007 (7) | −0.0011 (7) |
C44A | 0.0266 (9) | 0.0251 (8) | 0.0335 (9) | 0.0053 (7) | 0.0006 (7) | 0.0049 (7) |
C4A | 0.0245 (8) | 0.0201 (7) | 0.0252 (8) | −0.0017 (6) | 0.0067 (6) | −0.0008 (7) |
C5 | 0.0250 (8) | 0.0201 (7) | 0.0285 (8) | −0.0043 (6) | 0.0100 (7) | −0.0024 (7) |
O51 | 0.0326 (7) | 0.0265 (6) | 0.0344 (6) | −0.0002 (5) | 0.0112 (5) | −0.0097 (5) |
C6 | 0.0234 (9) | 0.0242 (8) | 0.0345 (9) | 0.0006 (6) | 0.0077 (7) | −0.0016 (7) |
C7 | 0.0244 (9) | 0.0221 (8) | 0.0281 (8) | 0.0016 (6) | 0.0050 (7) | 0.0003 (7) |
C71 | 0.0312 (10) | 0.0309 (9) | 0.0331 (9) | 0.0023 (7) | 0.0027 (7) | 0.0012 (8) |
C72 | 0.0321 (9) | 0.0271 (8) | 0.0352 (9) | −0.0003 (7) | 0.0086 (7) | 0.0027 (7) |
C8 | 0.0301 (9) | 0.0225 (8) | 0.0244 (8) | 0.0014 (6) | 0.0042 (7) | −0.0017 (7) |
C8A | 0.0270 (9) | 0.0184 (7) | 0.0253 (8) | −0.0011 (6) | 0.0070 (7) | 0.0001 (6) |
N9 | 0.0340 (8) | 0.0228 (6) | 0.0211 (6) | 0.0068 (6) | 0.0066 (6) | −0.0006 (5) |
C9A | 0.0261 (8) | 0.0207 (7) | 0.0248 (8) | 0.0010 (6) | 0.0063 (6) | 0.0010 (7) |
N1—C9A | 1.328 (2) | C47—C48 | 1.361 (2) |
N1—N2 | 1.366 (2) | C47—H47 | 0.9500 |
N2—C3 | 1.347 (2) | C48—C48A | 1.405 (2) |
N2—H2 | 0.8800 | C48—H48 | 0.9500 |
C3—C3A | 1.376 (2) | C48A—C44A | 1.422 (2) |
C3—C31 | 1.488 (2) | C4A—C8A | 1.370 (2) |
C31—H31A | 0.9800 | C4A—C5 | 1.436 (2) |
C31—H31B | 0.9800 | C5—O51 | 1.2374 (18) |
C31—H31C | 0.9800 | C5—C6 | 1.512 (2) |
C3A—C9A | 1.387 (2) | C6—C7 | 1.526 (2) |
C3A—C4 | 1.500 (2) | C6—H6A | 0.9900 |
C4—C4A | 1.523 (2) | C6—H6B | 0.9900 |
C4—C42 | 1.526 (2) | C7—C8 | 1.526 (2) |
C4—H4 | 1.0000 | C7—C71 | 1.527 (2) |
C41—C42 | 1.357 (2) | C7—C72 | 1.528 (2) |
C41—C48A | 1.426 (2) | C71—H71A | 0.9800 |
C41—H41 | 0.9500 | C71—H71B | 0.9800 |
C42—C43 | 1.417 (2) | C71—H71C | 0.9800 |
C43—C44 | 1.361 (2) | C72—H72A | 0.9800 |
C43—H43 | 0.9500 | C72—H72B | 0.9800 |
C44—C44A | 1.405 (2) | C72—H72C | 0.9800 |
C44—H44 | 0.9500 | C8—C8A | 1.502 (2) |
C45—C46 | 1.357 (2) | C8—H8A | 0.9900 |
C45—C44A | 1.413 (2) | C8—H8B | 0.9900 |
C45—H45 | 0.9500 | C8A—N9 | 1.358 (2) |
C46—C47 | 1.400 (3) | N9—C9A | 1.390 (2) |
C46—H46 | 0.9500 | N9—H9 | 0.8800 |
C9A—N1—N2 | 102.25 (12) | C44—C44A—C45 | 122.57 (16) |
C3—N2—N1 | 113.42 (12) | C44—C44A—C48A | 118.71 (15) |
C3—N2—H2 | 123.3 | C45—C44A—C48A | 118.71 (15) |
N1—N2—H2 | 123.3 | C8A—C4A—C5 | 119.39 (14) |
N2—C3—C3A | 106.17 (13) | C8A—C4A—C4 | 122.90 (13) |
N2—C3—C31 | 122.05 (14) | C5—C4A—C4 | 117.69 (13) |
C3A—C3—C31 | 131.78 (15) | O51—C5—C4A | 122.06 (14) |
C3—C31—H31A | 109.5 | O51—C5—C6 | 119.57 (13) |
C3—C31—H31B | 109.5 | C4A—C5—C6 | 118.35 (13) |
H31A—C31—H31B | 109.5 | C5—C6—C7 | 113.95 (12) |
C3—C31—H31C | 109.5 | C5—C6—H6A | 108.8 |
H31A—C31—H31C | 109.5 | C7—C6—H6A | 108.8 |
H31B—C31—H31C | 109.5 | C5—C6—H6B | 108.8 |
C3—C3A—C9A | 104.43 (13) | C7—C6—H6B | 108.8 |
C3—C3A—C4 | 134.37 (14) | H6A—C6—H6B | 107.7 |
C9A—C3A—C4 | 121.16 (13) | C8—C7—C6 | 107.33 (12) |
C3A—C4—C4A | 107.63 (12) | C8—C7—C71 | 109.07 (13) |
C3A—C4—C42 | 111.26 (12) | C6—C7—C71 | 110.06 (13) |
C4A—C4—C42 | 111.00 (12) | C8—C7—C72 | 110.77 (13) |
C3A—C4—H4 | 109.0 | C6—C7—C72 | 109.95 (13) |
C4A—C4—H4 | 109.0 | C71—C7—C72 | 109.63 (13) |
C42—C4—H4 | 109.0 | C7—C71—H71A | 109.5 |
C42—C41—C48A | 121.92 (15) | C7—C71—H71B | 109.5 |
C42—C41—H41 | 119.0 | H71A—C71—H71B | 109.5 |
C48A—C41—H41 | 119.0 | C7—C71—H71C | 109.5 |
C41—C42—C43 | 118.81 (15) | H71A—C71—H71C | 109.5 |
C41—C42—C4 | 121.89 (14) | H71B—C71—H71C | 109.5 |
C43—C42—C4 | 119.30 (13) | C7—C72—H72A | 109.5 |
C44—C43—C42 | 121.05 (15) | C7—C72—H72B | 109.5 |
C44—C43—H43 | 119.5 | H72A—C72—H72B | 109.5 |
C42—C43—H43 | 119.5 | C7—C72—H72C | 109.5 |
C43—C44—C44A | 121.18 (16) | H72A—C72—H72C | 109.5 |
C43—C44—H44 | 119.4 | H72B—C72—H72C | 109.5 |
C44A—C44—H44 | 119.4 | C8A—C8—C7 | 113.64 (13) |
C46—C45—C44A | 120.88 (17) | C8A—C8—H8A | 108.8 |
C46—C45—H45 | 119.6 | C7—C8—H8A | 108.8 |
C44A—C45—H45 | 119.6 | C8A—C8—H8B | 108.8 |
C45—C46—C47 | 120.05 (16) | C7—C8—H8B | 108.8 |
C45—C46—H46 | 120.0 | H8A—C8—H8B | 107.7 |
C47—C46—H46 | 120.0 | N9—C8A—C4A | 121.87 (14) |
C48—C47—C46 | 120.92 (17) | N9—C8A—C8 | 114.67 (13) |
C48—C47—H47 | 119.5 | C4A—C8A—C8 | 123.45 (14) |
C46—C47—H47 | 119.5 | C8A—N9—C9A | 117.82 (12) |
C47—C48—C48A | 120.52 (18) | C8A—N9—H9 | 121.1 |
C47—C48—H48 | 119.7 | C9A—N9—H9 | 121.1 |
C48A—C48—H48 | 119.7 | N1—C9A—C3A | 113.73 (13) |
C48—C48A—C44A | 118.85 (15) | N1—C9A—N9 | 123.43 (13) |
C48—C48A—C41 | 122.84 (16) | C3A—C9A—N9 | 122.69 (13) |
C44A—C48A—C41 | 118.30 (14) | ||
C9A—N1—N2—C3 | −0.59 (17) | C41—C48A—C44A—C45 | 177.35 (14) |
N1—N2—C3—C3A | 0.99 (18) | C3A—C4—C4A—C8A | 23.76 (19) |
N1—N2—C3—C31 | −178.09 (14) | C42—C4—C4A—C8A | −98.22 (16) |
N2—C3—C3A—C9A | −0.93 (17) | C3A—C4—C4A—C5 | −158.04 (13) |
C31—C3—C3A—C9A | 178.03 (16) | C42—C4—C4A—C5 | 79.98 (16) |
N2—C3—C3A—C4 | 176.73 (16) | C8A—C4A—C5—O51 | 179.87 (14) |
C31—C3—C3A—C4 | −4.3 (3) | C4—C4A—C5—O51 | 1.6 (2) |
C3—C3A—C4—C4A | 159.62 (17) | C8A—C4A—C5—C6 | −2.1 (2) |
C9A—C3A—C4—C4A | −23.03 (19) | C4—C4A—C5—C6 | 179.59 (12) |
C3—C3A—C4—C42 | −78.6 (2) | O51—C5—C6—C7 | −148.75 (14) |
C9A—C3A—C4—C42 | 98.79 (17) | C4A—C5—C6—C7 | 33.22 (19) |
C48A—C41—C42—C43 | 0.9 (2) | C5—C6—C7—C8 | −54.59 (16) |
C48A—C41—C42—C4 | −178.76 (13) | C5—C6—C7—C71 | −173.17 (13) |
C3A—C4—C42—C41 | 120.70 (15) | C5—C6—C7—C72 | 65.96 (17) |
C4A—C4—C42—C41 | −119.46 (16) | C6—C7—C8—C8A | 47.89 (17) |
C3A—C4—C42—C43 | −58.94 (18) | C71—C7—C8—C8A | 167.10 (13) |
C4A—C4—C42—C43 | 60.90 (18) | C72—C7—C8—C8A | −72.15 (17) |
C41—C42—C43—C44 | −1.4 (2) | C5—C4A—C8A—N9 | 174.52 (13) |
C4—C42—C43—C44 | 178.23 (14) | C4—C4A—C8A—N9 | −7.3 (2) |
C42—C43—C44—C44A | 0.4 (3) | C5—C4A—C8A—C8 | −4.2 (2) |
C44A—C45—C46—C47 | 0.6 (2) | C4—C4A—C8A—C8 | 173.99 (13) |
C45—C46—C47—C48 | −2.6 (3) | C7—C8—C8A—N9 | 160.58 (13) |
C46—C47—C48—C48A | 2.1 (3) | C7—C8—C8A—C4A | −20.6 (2) |
C47—C48—C48A—C44A | 0.4 (2) | C4A—C8A—N9—C9A | −12.4 (2) |
C47—C48—C48A—C41 | −179.23 (15) | C8—C8A—N9—C9A | 166.38 (13) |
C42—C41—C48A—C48 | −179.72 (15) | N2—N1—C9A—C3A | −0.06 (17) |
C42—C41—C48A—C44A | 0.6 (2) | N2—N1—C9A—N9 | 175.61 (14) |
C43—C44—C44A—C45 | −177.80 (15) | C3—C3A—C9A—N1 | 0.63 (18) |
C43—C44—C44A—C48A | 1.1 (2) | C4—C3A—C9A—N1 | −177.41 (13) |
C46—C45—C44A—C44 | −179.24 (15) | C3—C3A—C9A—N9 | −175.07 (14) |
C46—C45—C44A—C48A | 1.8 (2) | C4—C3A—C9A—N9 | 6.9 (2) |
C48—C48A—C44A—C44 | 178.70 (15) | C8A—N9—C9A—N1 | −162.52 (14) |
C41—C48A—C44A—C44 | −1.6 (2) | C8A—N9—C9A—C3A | 12.8 (2) |
C48—C48A—C44A—C45 | −2.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O51i | 0.88 | 1.95 | 2.810 (2) | 165 |
N9—H9···N1ii | 0.88 | 2.05 | 2.878 (2) | 155 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C23H23N3O |
Mr | 357.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 9.1222 (18), 15.281 (3), 14.346 (3) |
β (°) | 106.13 (3) |
V (Å3) | 1921.0 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.35 × 0.18 × 0.14 |
Data collection | |
Diffractometer | KappaCCD diffractometer |
Absorption correction | Multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.974, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16205, 4401, 2994 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.651 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.051, 0.137, 1.03 |
No. of reflections | 4401 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.28 |
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).
N1—C9A | 1.328 (2) | C8A—N9 | 1.358 (2) |
N1—N2 | 1.366 (2) | N9—C9A | 1.390 (2) |
N2—C3 | 1.347 (2) | ||
C9A—N1—N2 | 102.25 (12) | C8A—N9—C9A | 117.82 (12) |
C3—N2—N1 | 113.42 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O51i | 0.88 | 1.95 | 2.810 (2) | 165 |
N9—H9···N1ii | 0.88 | 2.05 | 2.878 (2) | 155 |
Symmetry codes: (i) −x, y+1/2, −z+3/2; (ii) −x, −y+1, −z+2. |
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Pyrazolo[3,4-b]quinolines are of interest as possible antiviral agents (Crenshaw et al., 1976, 1978; Smirnoff & Crenshaw, 1977). Some of their derivatives exhibit parasiticidic properties (Bristol-Meyers Co, 1973), and have been studied as potential antimalarial agents (Stein et al., 1970). Some pyrazolo[3,4-b]quinolines have shown bactericidal activity (Farghaly et al., 1989), have also been used as vasodilators (Bell & Ackerman, 1990) and evaluated for enzymatic inhibitory activity (Gatta et al., 1991).
In previous reports (Quiroga, Hormaza et al., 1998; Quiroga, Insuasty et al., 1998), we have reported an efficient and versatile synthesis of novel 4,7,8,9-tetrahydro-pyrimido- and 4,7,8,9-tetrahydropyrazolo[3,4-b]quinolin-5-ones from suitable pyrimidine and pyrazole amines to which dimedone and substituted benzaldehyde afford the ring annelation to quinoline.
Selected bonds and angles for the title compound, (I), are given in Table 1 and a molecular view is given in Fig. 1.
The hydrogen-bonding pattern comprises anti-parallel C(8) (N2–H2···O51i) chains linked together by R22(8) (N9–H9···N1ii) base-paired motifs (Bernstein et al., 1995). This combination forms a corrugated sheet which contains R66(34) rings. This is shown in Fig. 2. The details of the hydrogen bonds 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.