Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029455/hb2405sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029455/hb2405Isup2.hkl |
CCDC reference: 655604
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.147
- Data-to-parameter ratio = 14.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.38 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.40 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.63 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.43 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.43 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 2-(3,4-dimethoxyphenyl)acetonitrile (1.77 g, 10 mmol), 3,4,5-trimethoxybenzaldehyde (0.88 g, 10 mmol), and NaOEt (0.68 g, 10 mmol) in ethanol (5 ml) was stirred at room temperature and monitored by TLC. After completion of the reaction, 2 ml water was added and evaporated in vacuo. the product was purified through flash column chromatography and 50 mg of the title compound was dissolved in 100 ml absolute methanol and crystals suitable for X-ray analysis were grown by slow evaporation over a period of 15 d.
The O-bound H atoms were located in difference maps and their positions were freely refined with Uiso(H) = 1.2Ueq(O).
The C-bound H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
5-Aminopyrazoles posses many biological properties such as antibacterial (Kumar et al., 2005) and herbicidal activities (Jung et al., (2002). They can be prepared from substituted acetonitriles reacting with substituted hydrazines.
The title compound, (I), (Fig. 1) was obtained as part of our studies in this area and the X-ray analysis reveals that (I) is a enol with a conjugated system. There are two molecules in the asymmetric unit and intermolecular O—H···N hydrogen bonds (Table 1) help to stablize the crystal packing.
For background literature, see: Jung et al. (2002); Kumar et al. (2005).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids (arbitrary spheres for the H atoms). | |
Fig. 2. The reaction scheme for the formation of (I). |
C12H13NO3 | Z = 4 |
Mr = 219.23 | F(000) = 464 |
Triclinic, P1 | Dx = 1.321 Mg m−3 |
Hall symbol: -P 1 | Melting point = 478–480 K |
a = 8.5316 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1801 (17) Å | Cell parameters from 2572 reflections |
c = 11.8021 (18) Å | θ = 2.4–26.2° |
α = 82.777 (3)° | µ = 0.10 mm−1 |
β = 81.232 (2)° | T = 294 K |
γ = 85.712 (3)° | Prism, orange |
V = 1102.0 (3) Å3 | 0.26 × 0.24 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 4428 independent reflections |
Radiation source: fine-focus sealed tube | 3078 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 26.4°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −10→10 |
Tmin = 0.976, Tmax = 0.981 | k = −13→9 |
6372 measured reflections | l = −14→14 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0789P)2 + 0.2254P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.147 | (Δ/σ)max = 0.003 |
S = 1.03 | Δρmax = 0.43 e Å−3 |
4428 reflections | Δρmin = −0.39 e Å−3 |
297 parameters | Extinction correction: SHELXL97 |
0 restraints | Extinction coefficient: 0.019 (3) |
C12H13NO3 | γ = 85.712 (3)° |
Mr = 219.23 | V = 1102.0 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.5316 (13) Å | Mo Kα radiation |
b = 11.1801 (17) Å | µ = 0.10 mm−1 |
c = 11.8021 (18) Å | T = 294 K |
α = 82.777 (3)° | 0.26 × 0.24 × 0.20 mm |
β = 81.232 (2)° |
Bruker SMART CCD area-detector diffractometer | 4428 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 3078 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.981 | Rint = 0.017 |
6372 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.43 e Å−3 |
4428 reflections | Δρmin = −0.39 e Å−3 |
297 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | −0.0117 (2) | 0.27079 (18) | 0.68305 (17) | 0.0500 (5) | |
H1A | −0.0933 | 0.2146 | 0.6899 | 0.075* | |
H1B | 0.0173 | 0.3008 | 0.6033 | 0.075* | |
H1C | −0.0503 | 0.3369 | 0.7262 | 0.075* | |
C2 | 0.13047 (19) | 0.20862 (15) | 0.72932 (14) | 0.0367 (4) | |
C3 | 0.27142 (19) | 0.18544 (15) | 0.66240 (13) | 0.0348 (4) | |
C4 | 0.27460 (19) | 0.22417 (16) | 0.54200 (15) | 0.0415 (4) | |
C5 | 0.42067 (18) | 0.12585 (14) | 0.69735 (13) | 0.0340 (4) | |
C6 | 0.4403 (2) | 0.08622 (16) | 0.81096 (14) | 0.0435 (4) | |
H6 | 0.3560 | 0.0959 | 0.8697 | 0.052* | |
C7 | 0.5842 (2) | 0.03238 (17) | 0.83791 (15) | 0.0459 (4) | |
H7 | 0.5942 | 0.0061 | 0.9146 | 0.055* | |
C8 | 0.71225 (19) | 0.01707 (16) | 0.75376 (14) | 0.0408 (4) | |
C9 | 0.69499 (19) | 0.05794 (15) | 0.63854 (14) | 0.0380 (4) | |
C10 | 0.55151 (18) | 0.11012 (14) | 0.61176 (13) | 0.0363 (4) | |
H10 | 0.5412 | 0.1355 | 0.5350 | 0.044* | |
C11 | 0.8792 (2) | −0.07909 (19) | 0.88671 (16) | 0.0570 (5) | |
H11A | 0.8578 | −0.0153 | 0.9352 | 0.086* | |
H11B | 0.9864 | −0.1115 | 0.8881 | 0.086* | |
H11C | 0.8071 | −0.1417 | 0.9145 | 0.086* | |
C12 | 0.8223 (2) | 0.09421 (19) | 0.44412 (15) | 0.0545 (5) | |
H12A | 0.7447 | 0.0550 | 0.4131 | 0.082* | |
H12B | 0.9246 | 0.0827 | 0.3989 | 0.082* | |
H12C | 0.7933 | 0.1790 | 0.4421 | 0.082* | |
N1 | 0.27990 (19) | 0.25311 (16) | 0.44499 (14) | 0.0607 (5) | |
O1 | 0.11331 (15) | 0.17462 (12) | 0.84264 (10) | 0.0505 (3) | |
H1 | 0.015 (3) | 0.1997 (17) | 0.8758 (18) | 0.061* | |
O2 | 0.85876 (14) | −0.03284 (12) | 0.77157 (10) | 0.0549 (4) | |
O3 | 0.82865 (14) | 0.04373 (12) | 0.56009 (10) | 0.0519 (4) | |
C13 | 0.4089 (2) | 0.77590 (16) | −0.23875 (14) | 0.0442 (4) | |
H13A | 0.4517 | 0.8497 | −0.2774 | 0.066* | |
H13B | 0.3063 | 0.7933 | −0.1962 | 0.066* | |
H13C | 0.3989 | 0.7227 | −0.2947 | 0.066* | |
C14 | 0.51762 (19) | 0.71690 (15) | −0.15769 (14) | 0.0361 (4) | |
C15 | 0.47497 (18) | 0.69111 (15) | −0.04146 (13) | 0.0347 (4) | |
C16 | 0.3143 (2) | 0.72645 (16) | 0.00098 (14) | 0.0416 (4) | |
C17 | 0.57160 (19) | 0.62988 (14) | 0.04565 (13) | 0.0340 (4) | |
C18 | 0.50094 (19) | 0.61017 (14) | 0.16094 (13) | 0.0366 (4) | |
H18 | 0.3956 | 0.6370 | 0.1807 | 0.044* | |
C19 | 0.58282 (19) | 0.55206 (15) | 0.24623 (13) | 0.0377 (4) | |
C20 | 0.74174 (19) | 0.51091 (15) | 0.21806 (14) | 0.0378 (4) | |
C21 | 0.8120 (2) | 0.53047 (17) | 0.10525 (15) | 0.0476 (5) | |
H21 | 0.9174 | 0.5040 | 0.0855 | 0.057* | |
C22 | 0.7286 (2) | 0.58899 (17) | 0.01980 (15) | 0.0458 (5) | |
H22 | 0.7793 | 0.6009 | −0.0560 | 0.055* | |
C23 | 0.3598 (2) | 0.56599 (19) | 0.39341 (16) | 0.0517 (5) | |
H23A | 0.3456 | 0.6518 | 0.3748 | 0.078* | |
H23B | 0.3316 | 0.5452 | 0.4750 | 0.078* | |
H23C | 0.2932 | 0.5262 | 0.3530 | 0.078* | |
C24 | 0.9679 (2) | 0.39793 (19) | 0.28011 (18) | 0.0584 (5) | |
H24A | 0.9636 | 0.3387 | 0.2286 | 0.088* | |
H24B | 1.0046 | 0.3595 | 0.3494 | 0.088* | |
H24C | 1.0396 | 0.4581 | 0.2435 | 0.088* | |
N2 | 0.18624 (19) | 0.75399 (16) | 0.03788 (14) | 0.0599 (5) | |
O4 | 0.66561 (14) | 0.68852 (12) | −0.20565 (11) | 0.0493 (3) | |
H4 | 0.678 (2) | 0.7112 (17) | −0.2832 (19) | 0.059* | |
O5 | 0.52107 (14) | 0.52857 (13) | 0.35992 (10) | 0.0561 (4) | |
O6 | 0.81370 (14) | 0.45353 (12) | 0.30797 (10) | 0.0516 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0338 (9) | 0.0654 (12) | 0.0469 (11) | 0.0104 (8) | −0.0044 (8) | −0.0008 (9) |
C2 | 0.0340 (9) | 0.0433 (9) | 0.0302 (9) | 0.0032 (7) | −0.0028 (7) | 0.0003 (7) |
C3 | 0.0313 (8) | 0.0427 (9) | 0.0279 (8) | 0.0034 (7) | −0.0019 (7) | −0.0009 (7) |
C4 | 0.0308 (9) | 0.0561 (11) | 0.0336 (10) | 0.0085 (7) | −0.0025 (7) | 0.0004 (8) |
C5 | 0.0309 (8) | 0.0402 (9) | 0.0289 (8) | 0.0021 (7) | −0.0022 (7) | −0.0014 (6) |
C6 | 0.0335 (9) | 0.0630 (11) | 0.0296 (9) | 0.0084 (8) | 0.0002 (7) | −0.0006 (8) |
C7 | 0.0425 (10) | 0.0656 (12) | 0.0261 (9) | 0.0059 (8) | −0.0057 (7) | 0.0041 (8) |
C8 | 0.0326 (9) | 0.0536 (10) | 0.0337 (9) | 0.0051 (7) | −0.0071 (7) | 0.0031 (7) |
C9 | 0.0290 (8) | 0.0507 (10) | 0.0307 (9) | 0.0042 (7) | 0.0006 (7) | −0.0005 (7) |
C10 | 0.0335 (9) | 0.0489 (10) | 0.0231 (8) | 0.0047 (7) | −0.0020 (7) | 0.0017 (7) |
C11 | 0.0497 (11) | 0.0770 (14) | 0.0410 (11) | 0.0142 (10) | −0.0170 (9) | 0.0082 (9) |
C12 | 0.0423 (10) | 0.0804 (14) | 0.0328 (10) | 0.0138 (9) | 0.0017 (8) | 0.0055 (9) |
N1 | 0.0502 (10) | 0.0902 (13) | 0.0336 (9) | 0.0182 (9) | −0.0030 (7) | 0.0076 (8) |
O1 | 0.0365 (7) | 0.0771 (9) | 0.0312 (7) | 0.0129 (6) | 0.0028 (5) | 0.0012 (6) |
O2 | 0.0359 (7) | 0.0865 (10) | 0.0362 (7) | 0.0166 (6) | −0.0078 (5) | 0.0080 (6) |
O3 | 0.0327 (7) | 0.0836 (9) | 0.0312 (7) | 0.0171 (6) | 0.0006 (5) | 0.0070 (6) |
C13 | 0.0428 (10) | 0.0577 (11) | 0.0293 (9) | 0.0046 (8) | −0.0080 (7) | 0.0054 (7) |
C14 | 0.0335 (9) | 0.0447 (9) | 0.0283 (8) | 0.0032 (7) | −0.0048 (7) | 0.0002 (7) |
C15 | 0.0306 (8) | 0.0442 (9) | 0.0266 (8) | 0.0046 (7) | −0.0030 (6) | 0.0006 (7) |
C16 | 0.0402 (10) | 0.0548 (11) | 0.0264 (9) | 0.0104 (8) | −0.0056 (7) | 0.0014 (7) |
C17 | 0.0331 (8) | 0.0408 (9) | 0.0261 (8) | 0.0025 (7) | −0.0033 (6) | −0.0004 (6) |
C18 | 0.0298 (8) | 0.0492 (10) | 0.0272 (8) | 0.0083 (7) | −0.0015 (7) | 0.0000 (7) |
C19 | 0.0350 (9) | 0.0516 (10) | 0.0241 (8) | 0.0035 (7) | −0.0026 (7) | −0.0005 (7) |
C20 | 0.0318 (8) | 0.0510 (10) | 0.0287 (8) | 0.0047 (7) | −0.0074 (7) | 0.0022 (7) |
C21 | 0.0297 (9) | 0.0719 (12) | 0.0356 (10) | 0.0119 (8) | −0.0009 (7) | 0.0018 (8) |
C22 | 0.0347 (9) | 0.0694 (12) | 0.0269 (9) | 0.0095 (8) | 0.0013 (7) | 0.0052 (8) |
C23 | 0.0391 (10) | 0.0775 (13) | 0.0313 (9) | 0.0137 (9) | 0.0012 (8) | 0.0041 (8) |
C24 | 0.0365 (10) | 0.0782 (14) | 0.0547 (12) | 0.0152 (9) | −0.0115 (9) | 0.0097 (10) |
N2 | 0.0429 (9) | 0.0914 (13) | 0.0384 (9) | 0.0233 (8) | −0.0026 (7) | −0.0009 (8) |
O4 | 0.0370 (7) | 0.0786 (9) | 0.0244 (6) | 0.0107 (6) | 0.0021 (5) | 0.0080 (6) |
O5 | 0.0376 (7) | 0.0963 (10) | 0.0253 (6) | 0.0189 (6) | 0.0001 (5) | 0.0099 (6) |
O6 | 0.0355 (7) | 0.0800 (9) | 0.0339 (7) | 0.0143 (6) | −0.0086 (5) | 0.0081 (6) |
C1—C2 | 1.494 (2) | C13—C14 | 1.494 (2) |
C1—H1A | 0.9600 | C13—H13A | 0.9600 |
C1—H1B | 0.9600 | C13—H13B | 0.9600 |
C1—H1C | 0.9600 | C13—H13C | 0.9600 |
C2—O1 | 1.3325 (19) | C14—O4 | 1.3352 (19) |
C2—C3 | 1.361 (2) | C14—C15 | 1.364 (2) |
C3—C4 | 1.429 (2) | C15—C16 | 1.431 (2) |
C3—C5 | 1.483 (2) | C15—C17 | 1.484 (2) |
C4—N1 | 1.145 (2) | C16—N2 | 1.147 (2) |
C5—C6 | 1.389 (2) | C17—C22 | 1.384 (2) |
C5—C10 | 1.403 (2) | C17—C18 | 1.399 (2) |
C6—C7 | 1.390 (2) | C18—C19 | 1.380 (2) |
C6—H6 | 0.9300 | C18—H18 | 0.9300 |
C7—C8 | 1.376 (2) | C19—O5 | 1.365 (2) |
C7—H7 | 0.9300 | C19—C20 | 1.403 (2) |
C8—O2 | 1.3654 (19) | C20—O6 | 1.3722 (19) |
C8—C9 | 1.405 (2) | C20—C21 | 1.372 (2) |
C9—O3 | 1.3678 (19) | C21—C22 | 1.390 (2) |
C9—C10 | 1.380 (2) | C21—H21 | 0.9300 |
C10—H10 | 0.9300 | C22—H22 | 0.9300 |
C11—O2 | 1.424 (2) | C23—O5 | 1.419 (2) |
C11—H11A | 0.9600 | C23—H23A | 0.9600 |
C11—H11B | 0.9600 | C23—H23B | 0.9600 |
C11—H11C | 0.9600 | C23—H23C | 0.9600 |
C12—O3 | 1.421 (2) | C24—O6 | 1.422 (2) |
C12—H12A | 0.9600 | C24—H24A | 0.9600 |
C12—H12B | 0.9600 | C24—H24B | 0.9600 |
C12—H12C | 0.9600 | C24—H24C | 0.9600 |
O1—H1 | 0.91 (2) | O4—H4 | 0.91 (2) |
C2—C1—H1A | 109.5 | C14—C13—H13A | 109.5 |
C2—C1—H1B | 109.5 | C14—C13—H13B | 109.5 |
H1A—C1—H1B | 109.5 | H13A—C13—H13B | 109.5 |
C2—C1—H1C | 109.5 | C14—C13—H13C | 109.5 |
H1A—C1—H1C | 109.5 | H13A—C13—H13C | 109.5 |
H1B—C1—H1C | 109.5 | H13B—C13—H13C | 109.5 |
O1—C2—C3 | 120.05 (15) | O4—C14—C15 | 119.68 (14) |
O1—C2—C1 | 116.31 (15) | O4—C14—C13 | 115.77 (14) |
C3—C2—C1 | 123.64 (15) | C15—C14—C13 | 124.55 (15) |
C2—C3—C4 | 114.95 (14) | C14—C15—C16 | 115.05 (14) |
C2—C3—C5 | 128.93 (15) | C14—C15—C17 | 128.79 (15) |
C4—C3—C5 | 116.11 (14) | C16—C15—C17 | 116.15 (14) |
N1—C4—C3 | 178.38 (19) | N2—C16—C15 | 178.22 (18) |
C6—C5—C10 | 117.49 (14) | C22—C17—C18 | 117.27 (14) |
C6—C5—C3 | 123.81 (14) | C22—C17—C15 | 123.91 (14) |
C10—C5—C3 | 118.69 (14) | C18—C17—C15 | 118.81 (14) |
C5—C6—C7 | 120.86 (16) | C19—C18—C17 | 121.97 (14) |
C5—C6—H6 | 119.6 | C19—C18—H18 | 119.0 |
C7—C6—H6 | 119.6 | C17—C18—H18 | 119.0 |
C8—C7—C6 | 121.50 (16) | O5—C19—C18 | 125.13 (14) |
C8—C7—H7 | 119.3 | O5—C19—C20 | 115.04 (14) |
C6—C7—H7 | 119.3 | C18—C19—C20 | 119.82 (15) |
O2—C8—C7 | 125.90 (15) | O6—C20—C21 | 125.57 (15) |
O2—C8—C9 | 115.71 (14) | O6—C20—C19 | 115.94 (14) |
C7—C8—C9 | 118.37 (15) | C21—C20—C19 | 118.49 (14) |
O3—C9—C10 | 124.74 (15) | C20—C21—C22 | 121.35 (16) |
O3—C9—C8 | 115.17 (14) | C20—C21—H21 | 119.3 |
C10—C9—C8 | 120.07 (15) | C22—C21—H21 | 119.3 |
C9—C10—C5 | 121.70 (15) | C17—C22—C21 | 121.10 (16) |
C9—C10—H10 | 119.2 | C17—C22—H22 | 119.5 |
C5—C10—H10 | 119.2 | C21—C22—H22 | 119.5 |
O2—C11—H11A | 109.5 | O5—C23—H23A | 109.5 |
O2—C11—H11B | 109.5 | O5—C23—H23B | 109.5 |
H11A—C11—H11B | 109.5 | H23A—C23—H23B | 109.5 |
O2—C11—H11C | 109.5 | O5—C23—H23C | 109.5 |
H11A—C11—H11C | 109.5 | H23A—C23—H23C | 109.5 |
H11B—C11—H11C | 109.5 | H23B—C23—H23C | 109.5 |
O3—C12—H12A | 109.5 | O6—C24—H24A | 109.5 |
O3—C12—H12B | 109.5 | O6—C24—H24B | 109.5 |
H12A—C12—H12B | 109.5 | H24A—C24—H24B | 109.5 |
O3—C12—H12C | 109.5 | O6—C24—H24C | 109.5 |
H12A—C12—H12C | 109.5 | H24A—C24—H24C | 109.5 |
H12B—C12—H12C | 109.5 | H24B—C24—H24C | 109.5 |
C2—O1—H1 | 109.7 (13) | C14—O4—H4 | 110.4 (13) |
C8—O2—C11 | 117.32 (14) | C19—O5—C23 | 117.69 (13) |
C9—O3—C12 | 117.45 (13) | C20—O6—C24 | 117.18 (14) |
O1—C2—C3—C4 | 178.90 (15) | O4—C14—C15—C16 | 179.39 (15) |
C1—C2—C3—C4 | −0.6 (2) | C13—C14—C15—C16 | −0.8 (3) |
O1—C2—C3—C5 | −1.0 (3) | O4—C14—C15—C17 | −1.8 (3) |
C1—C2—C3—C5 | 179.46 (17) | C13—C14—C15—C17 | 178.01 (16) |
C2—C3—C5—C6 | −2.2 (3) | C14—C15—C17—C22 | 0.8 (3) |
C4—C3—C5—C6 | 177.82 (16) | C16—C15—C17—C22 | 179.58 (17) |
C2—C3—C5—C10 | 179.03 (17) | C14—C15—C17—C18 | −178.36 (17) |
C4—C3—C5—C10 | −0.9 (2) | C16—C15—C17—C18 | 0.5 (2) |
C10—C5—C6—C7 | −0.4 (3) | C22—C17—C18—C19 | −0.2 (3) |
C3—C5—C6—C7 | −179.17 (17) | C15—C17—C18—C19 | 178.93 (15) |
C5—C6—C7—C8 | 0.4 (3) | C17—C18—C19—O5 | −179.21 (16) |
C6—C7—C8—O2 | 178.91 (17) | C17—C18—C19—C20 | 0.0 (3) |
C6—C7—C8—C9 | 0.3 (3) | O5—C19—C20—O6 | −0.3 (2) |
O2—C8—C9—O3 | −1.0 (2) | C18—C19—C20—O6 | −179.62 (15) |
C7—C8—C9—O3 | 177.74 (16) | O5—C19—C20—C21 | 179.60 (16) |
O2—C8—C9—C10 | −179.79 (16) | C18—C19—C20—C21 | 0.3 (3) |
C7—C8—C9—C10 | −1.1 (3) | O6—C20—C21—C22 | 179.56 (17) |
O3—C9—C10—C5 | −177.60 (15) | C19—C20—C21—C22 | −0.4 (3) |
C8—C9—C10—C5 | 1.1 (3) | C18—C17—C22—C21 | 0.2 (3) |
C6—C5—C10—C9 | −0.3 (3) | C15—C17—C22—C21 | −178.94 (17) |
C3—C5—C10—C9 | 178.48 (15) | C20—C21—C22—C17 | 0.1 (3) |
C7—C8—O2—C11 | 3.5 (3) | C18—C19—O5—C23 | 0.4 (3) |
C9—C8—O2—C11 | −177.88 (16) | C20—C19—O5—C23 | −178.84 (16) |
C10—C9—O3—C12 | 4.8 (3) | C21—C20—O6—C24 | −7.4 (3) |
C8—C9—O3—C12 | −173.95 (17) | C19—C20—O6—C24 | 172.52 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.91 (2) | 1.93 (2) | 2.835 (2) | 173.7 (19) |
O4—H4···N1ii | 0.91 (2) | 1.89 (2) | 2.793 (2) | 174.3 (19) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C12H13NO3 |
Mr | 219.23 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 294 |
a, b, c (Å) | 8.5316 (13), 11.1801 (17), 11.8021 (18) |
α, β, γ (°) | 82.777 (3), 81.232 (2), 85.712 (3) |
V (Å3) | 1102.0 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.26 × 0.24 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.976, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6372, 4428, 3078 |
Rint | 0.017 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.147, 1.03 |
No. of reflections | 4428 |
No. of parameters | 297 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.39 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.91 (2) | 1.93 (2) | 2.835 (2) | 173.7 (19) |
O4—H4···N1ii | 0.91 (2) | 1.89 (2) | 2.793 (2) | 174.3 (19) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
5-Aminopyrazoles posses many biological properties such as antibacterial (Kumar et al., 2005) and herbicidal activities (Jung et al., (2002). They can be prepared from substituted acetonitriles reacting with substituted hydrazines.
The title compound, (I), (Fig. 1) was obtained as part of our studies in this area and the X-ray analysis reveals that (I) is a enol with a conjugated system. There are two molecules in the asymmetric unit and intermolecular O—H···N hydrogen bonds (Table 1) help to stablize the crystal packing.