The non-H atoms of the title molecule, C
13H
14N
2O
3, are approximately coplanar. The molecules are linked into a two-dimensional network parallel to the
bc plane by intermolecular N—H
O, C—H
O and C—H
π interactions.
Supporting information
CCDC reference: 640301
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.131
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
0 ALERT level A = In general: serious problem
0 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
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
Data collection: APEX2 Software Suite (Bruker, 2005); cell refinement: APEX2 Software Suite; data reduction: APEX2 Software Suite; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: WinGX (Farrugia,1999).
Ethyl 3-(2-hydroxy-5-methylphenyl)-1
H-pyrazole-5-carboxylate
top
Crystal data top
C13H14N2O3 | F(000) = 1040 |
Mr = 246.26 | Dx = 1.252 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2638 reflections |
a = 11.3626 (2) Å | θ = 2.8–26.2° |
b = 9.6712 (2) Å | µ = 0.09 mm−1 |
c = 23.8238 (4) Å | T = 296 K |
β = 93.170 (1)° | Block, colourless |
V = 2613.99 (8) Å3 | 0.33 × 0.31 × 0.17 mm |
Z = 8 | |
Data collection top
Bruker APEX2 CCD area-detector diffractometer | 2969 independent reflections |
Radiation source: fine-focus sealed tube | 2156 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.4°, θmin = 1.7° |
Absorption correction: multi-scan (APEX2 Software Suite; Bruker, 2005) | h = −14→14 |
Tmin = 0.971, Tmax = 0.985 | k = −11→12 |
9396 measured reflections | l = −30→30 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.8447P] where P = (Fo2 + 2Fc2)/3 |
2969 reflections | (Δ/σ)max = 0.024 |
170 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.19 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 | |
C1 | 0.4403 (2) | −0.3247 (2) | 0.01781 (8) | 0.0827 (6) | |
H1A | 0.3816 | −0.2957 | −0.0103 | 0.124* | |
H1B | 0.4418 | −0.4238 | 0.0197 | 0.124* | |
H1C | 0.5162 | −0.2913 | 0.0082 | 0.124* | |
C2 | 0.41112 (14) | −0.26696 (17) | 0.07405 (7) | 0.0555 (4) | |
C3 | 0.43069 (15) | −0.34260 (18) | 0.12316 (7) | 0.0610 (4) | |
H3 | 0.4621 | −0.4311 | 0.1212 | 0.073* | |
C4 | 0.40484 (15) | −0.29010 (18) | 0.17443 (7) | 0.0598 (4) | |
H4 | 0.4191 | −0.3430 | 0.2067 | 0.072* | |
C5 | 0.35765 (13) | −0.15881 (16) | 0.17855 (6) | 0.0493 (4) | |
C6 | 0.33469 (12) | −0.07948 (14) | 0.12988 (5) | 0.0430 (3) | |
C7 | 0.36305 (13) | −0.13597 (16) | 0.07853 (6) | 0.0486 (4) | |
H7 | 0.3492 | −0.0838 | 0.0460 | 0.058* | |
C8 | 0.28468 (12) | 0.06018 (15) | 0.13250 (5) | 0.0428 (3) | |
C9 | 0.26373 (12) | 0.15891 (15) | 0.09002 (6) | 0.0461 (3) | |
H9 | 0.2763 | 0.1496 | 0.0520 | 0.055* | |
C10 | 0.22063 (13) | 0.27221 (15) | 0.11673 (6) | 0.0458 (3) | |
C11 | 0.18168 (13) | 0.40815 (16) | 0.09463 (6) | 0.0487 (4) | |
C12 | 0.10350 (14) | 0.62503 (16) | 0.12028 (7) | 0.0573 (4) | |
H12A | 0.0366 | 0.6179 | 0.0933 | 0.069* | |
H12B | 0.1649 | 0.6778 | 0.1034 | 0.069* | |
C13 | 0.06754 (17) | 0.6950 (2) | 0.17277 (8) | 0.0731 (5) | |
H13A | 0.0075 | 0.6414 | 0.1894 | 0.110* | |
H13B | 0.0375 | 0.7855 | 0.1637 | 0.110* | |
H13C | 0.1346 | 0.7030 | 0.1989 | 0.110* | |
N1 | 0.25484 (11) | 0.11197 (13) | 0.18221 (5) | 0.0496 (3) | |
N2 | 0.21707 (11) | 0.24065 (13) | 0.17148 (5) | 0.0486 (3) | |
O1 | 0.33473 (12) | −0.11152 (13) | 0.23085 (4) | 0.0657 (3) | |
H1 | 0.3059 | −0.0339 | 0.2282 | 0.099* | |
O2 | 0.18144 (12) | 0.44020 (13) | 0.04599 (5) | 0.0712 (4) | |
O3 | 0.14646 (10) | 0.48863 (11) | 0.13579 (4) | 0.0531 (3) | |
H2 | 0.1905 (15) | 0.2905 (18) | 0.1991 (7) | 0.061 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.1114 (15) | 0.0680 (12) | 0.0689 (12) | 0.0251 (12) | 0.0077 (11) | −0.0157 (10) |
C2 | 0.0594 (8) | 0.0507 (9) | 0.0563 (9) | 0.0042 (7) | 0.0032 (7) | −0.0046 (7) |
C3 | 0.0647 (9) | 0.0464 (9) | 0.0714 (11) | 0.0096 (8) | −0.0017 (8) | 0.0023 (8) |
C4 | 0.0685 (10) | 0.0530 (10) | 0.0571 (9) | 0.0013 (8) | −0.0033 (7) | 0.0135 (7) |
C5 | 0.0559 (8) | 0.0500 (9) | 0.0420 (8) | −0.0055 (7) | 0.0032 (6) | 0.0049 (6) |
C6 | 0.0474 (7) | 0.0420 (8) | 0.0395 (7) | −0.0043 (6) | 0.0028 (5) | 0.0022 (6) |
C7 | 0.0584 (8) | 0.0457 (8) | 0.0416 (7) | 0.0009 (7) | 0.0027 (6) | 0.0002 (6) |
C8 | 0.0493 (7) | 0.0437 (8) | 0.0356 (7) | −0.0044 (6) | 0.0049 (5) | −0.0005 (6) |
C9 | 0.0569 (8) | 0.0480 (8) | 0.0339 (7) | 0.0010 (7) | 0.0068 (5) | −0.0002 (6) |
C10 | 0.0558 (8) | 0.0459 (8) | 0.0362 (7) | −0.0020 (6) | 0.0070 (5) | −0.0003 (6) |
C11 | 0.0573 (8) | 0.0476 (8) | 0.0416 (8) | −0.0005 (7) | 0.0071 (6) | −0.0001 (6) |
C12 | 0.0595 (9) | 0.0446 (9) | 0.0680 (10) | 0.0012 (7) | 0.0041 (7) | 0.0040 (7) |
C13 | 0.0712 (11) | 0.0596 (11) | 0.0889 (14) | 0.0060 (9) | 0.0082 (9) | −0.0169 (10) |
N1 | 0.0669 (8) | 0.0460 (7) | 0.0366 (6) | 0.0013 (6) | 0.0078 (5) | −0.0003 (5) |
N2 | 0.0648 (7) | 0.0449 (7) | 0.0367 (6) | 0.0018 (6) | 0.0089 (5) | −0.0027 (5) |
O1 | 0.0994 (9) | 0.0600 (7) | 0.0385 (6) | 0.0027 (7) | 0.0094 (5) | 0.0096 (5) |
O2 | 0.1088 (10) | 0.0624 (8) | 0.0433 (6) | 0.0143 (7) | 0.0132 (6) | 0.0091 (5) |
O3 | 0.0692 (7) | 0.0429 (6) | 0.0477 (6) | 0.0046 (5) | 0.0086 (5) | −0.0007 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.505 (2) | C9—C10 | 1.371 (2) |
C1—H1A | 0.96 | C9—H9 | 0.93 |
C1—H1B | 0.96 | C10—N2 | 1.3424 (17) |
C1—H1C | 0.96 | C10—C11 | 1.475 (2) |
C2—C7 | 1.386 (2) | C11—O2 | 1.1993 (17) |
C2—C3 | 1.387 (2) | C11—O3 | 1.3307 (17) |
C3—C4 | 1.370 (2) | C12—O3 | 1.4474 (19) |
C3—H3 | 0.93 | C12—C13 | 1.498 (2) |
C4—C5 | 1.384 (2) | C12—H12A | 0.97 |
C4—H4 | 0.93 | C12—H12B | 0.97 |
C5—O1 | 1.3657 (18) | C13—H13A | 0.96 |
C5—C6 | 1.4028 (19) | C13—H13B | 0.96 |
C6—C7 | 1.3938 (19) | C13—H13C | 0.96 |
C6—C8 | 1.468 (2) | N1—N2 | 1.3365 (17) |
C7—H7 | 0.93 | N2—H2 | 0.884 (18) |
C8—N1 | 1.3464 (17) | O1—H1 | 0.82 |
C8—C9 | 1.4022 (19) | | |
| | | |
C2—C1—H1A | 109.5 | C10—C9—C8 | 105.08 (12) |
C2—C1—H1B | 109.5 | C10—C9—H9 | 127.5 |
H1A—C1—H1B | 109.5 | C8—C9—H9 | 127.5 |
C2—C1—H1C | 109.5 | N2—C10—C9 | 107.45 (13) |
H1A—C1—H1C | 109.5 | N2—C10—C11 | 121.66 (13) |
H1B—C1—H1C | 109.5 | C9—C10—C11 | 130.89 (13) |
C7—C2—C3 | 117.55 (15) | O2—C11—O3 | 125.17 (14) |
C7—C2—C1 | 120.98 (15) | O2—C11—C10 | 124.04 (14) |
C3—C2—C1 | 121.48 (16) | O3—C11—C10 | 110.79 (12) |
C4—C3—C2 | 121.63 (16) | O3—C12—C13 | 107.60 (13) |
C4—C3—H3 | 119.2 | O3—C12—H12A | 110.2 |
C2—C3—H3 | 119.2 | C13—C12—H12A | 110.2 |
C3—C4—C5 | 120.42 (15) | O3—C12—H12B | 110.2 |
C3—C4—H4 | 119.8 | C13—C12—H12B | 110.2 |
C5—C4—H4 | 119.8 | H12A—C12—H12B | 108.5 |
O1—C5—C4 | 117.79 (13) | C12—C13—H13A | 109.5 |
O1—C5—C6 | 122.33 (14) | C12—C13—H13B | 109.5 |
C4—C5—C6 | 119.89 (14) | H13A—C13—H13B | 109.5 |
C7—C6—C5 | 118.01 (13) | C12—C13—H13C | 109.5 |
C7—C6—C8 | 120.45 (12) | H13A—C13—H13C | 109.5 |
C5—C6—C8 | 121.52 (13) | H13B—C13—H13C | 109.5 |
C2—C7—C6 | 122.48 (14) | N2—N1—C8 | 105.78 (11) |
C2—C7—H7 | 118.8 | N1—N2—C10 | 111.78 (12) |
C6—C7—H7 | 118.8 | N1—N2—H2 | 119.0 (11) |
N1—C8—C9 | 109.91 (13) | C10—N2—H2 | 129.1 (11) |
N1—C8—C6 | 119.78 (12) | C5—O1—H1 | 109.5 |
C9—C8—C6 | 130.28 (12) | C11—O3—C12 | 117.12 (12) |
| | | |
C7—C2—C3—C4 | −0.6 (2) | N1—C8—C9—C10 | 0.32 (16) |
C1—C2—C3—C4 | 179.63 (17) | C6—C8—C9—C10 | −177.57 (14) |
C2—C3—C4—C5 | 0.2 (3) | C8—C9—C10—N2 | 0.07 (16) |
C3—C4—C5—O1 | −179.39 (14) | C8—C9—C10—C11 | −179.51 (14) |
C3—C4—C5—C6 | 0.8 (2) | N2—C10—C11—O2 | −178.74 (15) |
O1—C5—C6—C7 | 178.91 (13) | C9—C10—C11—O2 | 0.8 (3) |
C4—C5—C6—C7 | −1.3 (2) | N2—C10—C11—O3 | 0.8 (2) |
O1—C5—C6—C8 | 0.2 (2) | C9—C10—C11—O3 | −179.70 (14) |
C4—C5—C6—C8 | 180.00 (13) | C9—C8—N1—N2 | −0.57 (16) |
C3—C2—C7—C6 | 0.1 (2) | C6—C8—N1—N2 | 177.57 (12) |
C1—C2—C7—C6 | 179.83 (16) | C8—N1—N2—C10 | 0.62 (16) |
C5—C6—C7—C2 | 0.9 (2) | C9—C10—N2—N1 | −0.44 (17) |
C8—C6—C7—C2 | 179.57 (13) | C11—C10—N2—N1 | 179.19 (13) |
C7—C6—C8—N1 | 178.26 (12) | O2—C11—O3—C12 | 0.6 (2) |
C5—C6—C8—N1 | −3.1 (2) | C10—C11—O3—C12 | −178.88 (12) |
C7—C6—C8—C9 | −4.0 (2) | C13—C12—O3—C11 | 179.14 (13) |
C5—C6—C8—C9 | 174.63 (14) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.86 | 2.5926 (16) | 148 |
N2—H2···O1i | 0.88 (2) | 1.95 (2) | 2.8209 (16) | 167 (2) |
C9—H9···O2ii | 0.93 | 2.56 | 3.4684 (19) | 166 |
C12—H12B···Cg1iii | 0.97 | 2.73 | 3.5467 (17) | 142 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) x, y+1, z. |