In the title compound, C
13H
12N
2O
3, the phenyl ring is nearly planar, with a maximum deviation of 0.012 (1) Å. The pyrazole ring is planar and forms a 48.45 (5)° dihedral angle with the phenyl ring. There is an intramolecular O—H
O hydrogen bond between the hydroxy group and the ketone group. The packing is governed by weak C—H
N,O interactions.
Supporting information
CCDC reference: 239284
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.109
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.95
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
1 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
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Crystal data top
C13H12N2O3 | F(000) = 512 |
Mr = 244.25 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 7.5389 (12) Å | θ = 2.4–25.7° |
b = 10.3932 (13) Å | µ = 0.10 mm−1 |
c = 14.8992 (13) Å | T = 293 K |
β = 93.881 (6)° | Prism, colourless |
V = 1164.7 (3) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.024 |
ω/2θ scans | θmax = 25.7° |
Absorption correction: ψ scan empirical (using intensity measurements) via ψ scans (Fair, 1990) | h = 0→9 |
Tmin = 0.976, Tmax = 0.985 | k = −12→0 |
2277 measured reflections | l = −18→17 |
2221 independent reflections | 3 standard reflections every 120 min |
1356 reflections with I > 2σ(I) | intensity decay: 0.7% |
Refinement top
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0505P)2 + 0.1554P] where P = (Fo2 + 2Fc2)/3 |
2221 reflections | (Δ/σ)max < 0.001 |
166 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.27095 (19) | −0.09949 (14) | 0.62091 (9) | 0.0350 (4) | |
N2 | 0.3113 (2) | 0.00719 (14) | 0.57382 (10) | 0.0371 (4) | |
O1 | 0.0607 (2) | −0.13629 (16) | 0.33089 (9) | 0.0610 (4) | |
O2 | 0.2138 (2) | 0.07934 (16) | 0.34214 (9) | 0.0678 (5) | |
H2 | 0.1685 | 0.0079 | 0.3356 | 0.102* | |
O3 | 0.3403 (2) | 0.19399 (15) | 0.45157 (10) | 0.0618 (5) | |
C1 | 0.1775 (2) | −0.18762 (18) | 0.57015 (12) | 0.0361 (4) | |
C2 | 0.1576 (2) | −0.13589 (18) | 0.48353 (11) | 0.0363 (5) | |
C3 | 0.2441 (2) | −0.01361 (18) | 0.49094 (11) | 0.0362 (5) | |
C4 | 0.3312 (2) | −0.10389 (18) | 0.71483 (11) | 0.0349 (4) | |
C5 | 0.3019 (3) | 0.00156 (19) | 0.76779 (12) | 0.0429 (5) | |
H5 | 0.2421 | 0.0731 | 0.7435 | 0.051* | |
C6 | 0.3625 (3) | −0.0001 (2) | 0.85737 (13) | 0.0493 (5) | |
H6 | 0.3449 | 0.0709 | 0.8937 | 0.059* | |
C7 | 0.4492 (3) | −0.1074 (2) | 0.89268 (13) | 0.0496 (6) | |
H7 | 0.4886 | −0.1090 | 0.9532 | 0.059* | |
C8 | 0.4776 (3) | −0.2117 (2) | 0.83936 (13) | 0.0490 (6) | |
H8 | 0.5353 | −0.2840 | 0.8639 | 0.059* | |
C9 | 0.4209 (3) | −0.20984 (19) | 0.74931 (13) | 0.0437 (5) | |
H9 | 0.4431 | −0.2794 | 0.7125 | 0.052* | |
C10 | 0.1131 (3) | −0.3089 (2) | 0.61055 (14) | 0.0546 (6) | |
H10A | 0.1866 | −0.3794 | 0.5942 | 0.082* | |
H10B | −0.0076 | −0.3246 | 0.5885 | 0.082* | |
H10C | 0.1188 | −0.3006 | 0.6749 | 0.082* | |
C11 | 0.0646 (3) | −0.1932 (2) | 0.40389 (13) | 0.0442 (5) | |
C12 | −0.0300 (3) | −0.3183 (2) | 0.40682 (15) | 0.0627 (7) | |
H12A | −0.1296 | −0.3099 | 0.4433 | 0.094* | |
H12B | 0.0497 | −0.3827 | 0.4321 | 0.094* | |
H12C | −0.0713 | −0.3430 | 0.3469 | 0.094* | |
C13 | 0.2708 (3) | 0.0949 (2) | 0.42630 (13) | 0.0454 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0387 (9) | 0.0356 (9) | 0.0303 (8) | −0.0017 (8) | −0.0014 (7) | 0.0017 (7) |
N2 | 0.0398 (9) | 0.0363 (9) | 0.0352 (9) | 0.0003 (8) | 0.0017 (7) | 0.0032 (7) |
O1 | 0.0633 (10) | 0.0824 (11) | 0.0357 (8) | 0.0026 (9) | −0.0081 (7) | −0.0049 (8) |
O2 | 0.0873 (13) | 0.0781 (12) | 0.0369 (9) | −0.0072 (10) | −0.0029 (8) | 0.0142 (8) |
O3 | 0.0838 (12) | 0.0485 (9) | 0.0532 (9) | −0.0077 (9) | 0.0043 (8) | 0.0103 (8) |
C1 | 0.0345 (11) | 0.0368 (10) | 0.0370 (10) | −0.0003 (9) | 0.0020 (8) | −0.0024 (9) |
C2 | 0.0345 (10) | 0.0409 (11) | 0.0334 (10) | 0.0043 (9) | 0.0028 (8) | −0.0073 (9) |
C3 | 0.0352 (11) | 0.0433 (11) | 0.0304 (10) | 0.0079 (9) | 0.0041 (8) | −0.0001 (8) |
C4 | 0.0346 (11) | 0.0386 (11) | 0.0309 (10) | −0.0036 (9) | −0.0010 (8) | 0.0028 (8) |
C5 | 0.0467 (12) | 0.0404 (11) | 0.0406 (11) | 0.0044 (10) | −0.0040 (9) | 0.0004 (9) |
C6 | 0.0568 (14) | 0.0527 (13) | 0.0377 (11) | 0.0016 (12) | −0.0020 (10) | −0.0073 (10) |
C7 | 0.0517 (13) | 0.0604 (14) | 0.0350 (11) | −0.0009 (12) | −0.0091 (9) | 0.0031 (10) |
C8 | 0.0491 (13) | 0.0483 (13) | 0.0481 (12) | 0.0069 (11) | −0.0070 (10) | 0.0095 (10) |
C9 | 0.0455 (12) | 0.0410 (11) | 0.0439 (12) | 0.0033 (10) | −0.0015 (9) | −0.0012 (9) |
C10 | 0.0619 (14) | 0.0496 (13) | 0.0509 (13) | −0.0141 (12) | −0.0061 (11) | 0.0036 (10) |
C11 | 0.0335 (11) | 0.0592 (13) | 0.0394 (12) | 0.0111 (10) | 0.0000 (9) | −0.0114 (10) |
C12 | 0.0589 (15) | 0.0689 (16) | 0.0590 (14) | −0.0117 (13) | −0.0059 (11) | −0.0216 (12) |
C13 | 0.0456 (13) | 0.0530 (13) | 0.0381 (12) | 0.0077 (11) | 0.0061 (9) | 0.0052 (10) |
Geometric parameters (Å, º) top
N1—C1 | 1.355 (2) | C5—H5 | 0.9300 |
N1—N2 | 1.358 (2) | C6—C7 | 1.379 (3) |
N1—C4 | 1.442 (2) | C6—H6 | 0.9300 |
N2—C3 | 1.320 (2) | C7—C8 | 1.369 (3) |
O1—C11 | 1.237 (2) | C7—H7 | 0.9300 |
O2—C13 | 1.308 (2) | C8—C9 | 1.381 (3) |
O2—H2 | 0.8200 | C8—H8 | 0.9300 |
O3—C13 | 1.204 (2) | C9—H9 | 0.9300 |
C1—C2 | 1.397 (2) | C10—H10A | 0.9600 |
C1—C10 | 1.492 (3) | C10—H10B | 0.9600 |
C2—C3 | 1.429 (3) | C10—H10C | 0.9600 |
C2—C11 | 1.463 (3) | C11—C12 | 1.485 (3) |
C3—C13 | 1.505 (3) | C12—H12A | 0.9600 |
C4—C9 | 1.374 (3) | C12—H12B | 0.9600 |
C4—C5 | 1.377 (3) | C12—H12C | 0.9600 |
C5—C6 | 1.381 (3) | | |
| | | |
C1—N1—N2 | 112.95 (14) | C6—C7—H7 | 119.7 |
C1—N1—C4 | 129.64 (15) | C7—C8—C9 | 120.16 (19) |
N2—N1—C4 | 117.41 (14) | C7—C8—H8 | 119.9 |
C3—N2—N1 | 105.32 (15) | C9—C8—H8 | 119.9 |
C13—O2—H2 | 109.5 | C4—C9—C8 | 119.14 (19) |
N1—C1—C2 | 105.96 (16) | C4—C9—H9 | 120.4 |
N1—C1—C10 | 121.14 (16) | C8—C9—H9 | 120.4 |
C2—C1—C10 | 132.85 (17) | C1—C10—H10A | 109.5 |
C1—C2—C3 | 104.52 (15) | C1—C10—H10B | 109.5 |
C1—C2—C11 | 127.47 (18) | H10A—C10—H10B | 109.5 |
C3—C2—C11 | 127.99 (17) | C1—C10—H10C | 109.5 |
N2—C3—C2 | 111.23 (16) | H10A—C10—H10C | 109.5 |
N2—C3—C13 | 114.59 (17) | H10B—C10—H10C | 109.5 |
C2—C3—C13 | 134.17 (17) | O1—C11—C2 | 120.00 (19) |
C9—C4—C5 | 121.18 (17) | O1—C11—C12 | 117.51 (18) |
C9—C4—N1 | 120.20 (16) | C2—C11—C12 | 122.49 (19) |
C5—C4—N1 | 118.59 (16) | C11—C12—H12A | 109.5 |
C4—C5—C6 | 119.23 (18) | C11—C12—H12B | 109.5 |
C4—C5—H5 | 120.4 | H12A—C12—H12B | 109.5 |
C6—C5—H5 | 120.4 | C11—C12—H12C | 109.5 |
C7—C6—C5 | 119.74 (19) | H12A—C12—H12C | 109.5 |
C7—C6—H6 | 120.1 | H12B—C12—H12C | 109.5 |
C5—C6—H6 | 120.1 | O3—C13—O2 | 120.88 (19) |
C8—C7—C6 | 120.51 (18) | O3—C13—C3 | 121.00 (18) |
C8—C7—H7 | 119.7 | O2—C13—C3 | 118.11 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.82 | 1.70 | 2.521 (2) | 174 |
C5—H5···O1i | 0.93 | 2.56 | 3.325 (2) | 140 |
C6—H6···O3ii | 0.93 | 2.59 | 3.486 (3) | 161 |
C10—H10C···O1iii | 0.96 | 2.48 | 3.381 (2) | 156 |
Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y+1/2, z+1/2; (iii) x, −y−1/2, z+1/2. |