Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033363/kp2120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033363/kp2120Isup2.hkl |
CCDC reference: 657746
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.164
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Jia et al. (2004); Cottineau et al. (2002); Finn et al. (2003); Wei et al. (2006); Xia et al. (2007).
For related literature, see: Ding et al. (2007).
A mixture of ethyl 1-benzyl-3-phenyl-1H-pyrazole-5-carboxylate (0.01 mol) and potassium hydroxide (0.02 mol) in ethanol (40 ml) was heated to reflux for 2 h (Ding et al., 2007). The solvent was removed under reduced pressure and the residue was dissolved in water and acidified with hydrochloric acid (10%). The precipitate was filtered and dried to give a white solid (yield 80%). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of a solution of the solid in acetone at room temperature for 6 d.
All H atoms were placed at geometrically calculated positions and allowed to ride with C—H = 0.97 Å (for CH2 groups), and O—H = 0.82 Å; their isotropic displacement parameters were set to 1.2 times (CH2 groups) or 1.5 times (O—H groups) the equivalent displacement parameter of their parent atoms.
Pyrazole moiety plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), antipyretic, antibacterial, hypoglycaemic, antihyperglycaemic, analgesic, anti-inflammatory, sedative-hypnotic (Cottineau et al., 2002; Finn et al., 2003), and antitumour (Wei et al., 2006) activities. We report here the crystal structure of the title compound (I).
For related literature, see: Jia et al. (2004); Cottineau et al. (2002); Finn et al. (2003); Wei et al. (2006); Xia et al. (2007).
For related literature, see: Ding et al. (2007).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: APEX2; 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).
C17H14N2O2 | F(000) = 584 |
Mr = 278.30 | Dx = 1.325 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1764 (5) Å | Cell parameters from 2168 reflections |
b = 5.3356 (2) Å | θ = 3.1–24.9° |
c = 20.6646 (7) Å | µ = 0.09 mm−1 |
β = 106.132 (3)° | T = 293 K |
V = 1395.60 (9) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.21 × 0.17 mm |
Bruker APEXII CCD area-detector diffractometer | 3175 independent reflections |
Radiation source: fine-focus sealed tube | 1921 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | h = −17→16 |
Tmin = 0.974, Tmax = 0.985 | k = −6→6 |
8816 measured reflections | l = −26→24 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.1P)2 + 0.212P] where P = (Fo2 + 2Fc2)/3 |
3175 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
C17H14N2O2 | V = 1395.60 (9) Å3 |
Mr = 278.30 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 13.1764 (5) Å | µ = 0.09 mm−1 |
b = 5.3356 (2) Å | T = 293 K |
c = 20.6646 (7) Å | 0.30 × 0.21 × 0.17 mm |
β = 106.132 (3)° |
Bruker APEXII CCD area-detector diffractometer | 3175 independent reflections |
Absorption correction: multi-scan (APEX2; Bruker, 2005) | 1921 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.985 | Rint = 0.035 |
8816 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.15 e Å−3 |
3175 reflections | Δρmin = −0.19 e Å−3 |
191 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 | 0.3797 (2) | −0.3005 (5) | 0.34905 (13) | 0.0702 (7) | |
H1 | 0.4076 | −0.4120 | 0.3239 | 0.084* | |
C2 | 0.2974 (2) | −0.1482 (5) | 0.31785 (12) | 0.0722 (7) | |
H2 | 0.2690 | −0.1573 | 0.2714 | 0.087* | |
C3 | 0.25613 (19) | 0.0193 (4) | 0.35477 (10) | 0.0584 (6) | |
H3 | 0.2004 | 0.1230 | 0.3329 | 0.070* | |
C4 | 0.29696 (15) | 0.0340 (4) | 0.42403 (9) | 0.0445 (5) | |
C5 | 0.37994 (17) | −0.1229 (4) | 0.45512 (11) | 0.0560 (6) | |
H5 | 0.4082 | −0.1167 | 0.5016 | 0.067* | |
C6 | 0.42100 (19) | −0.2885 (5) | 0.41757 (13) | 0.0664 (6) | |
H6 | 0.4770 | −0.3923 | 0.4389 | 0.080* | |
C7 | 0.25032 (14) | 0.2085 (4) | 0.46310 (9) | 0.0411 (4) | |
C8 | 0.18501 (15) | 0.4147 (4) | 0.44101 (9) | 0.0443 (5) | |
H8 | 0.1629 | 0.4779 | 0.3974 | 0.053* | |
C9 | 0.15998 (14) | 0.5055 (4) | 0.49666 (9) | 0.0407 (4) | |
C10 | 0.09260 (14) | 0.7196 (4) | 0.50114 (9) | 0.0419 (4) | |
C11 | 0.20965 (16) | 0.3581 (4) | 0.61995 (9) | 0.0484 (5) | |
H11A | 0.2045 | 0.1871 | 0.6347 | 0.058* | |
H11B | 0.1475 | 0.4476 | 0.6237 | 0.058* | |
C12 | 0.30615 (15) | 0.4784 (4) | 0.66620 (9) | 0.0440 (5) | |
C13 | 0.35187 (18) | 0.6884 (4) | 0.64740 (12) | 0.0591 (6) | |
H13 | 0.3252 | 0.7545 | 0.6044 | 0.071* | |
C14 | 0.4374 (2) | 0.8010 (5) | 0.69235 (15) | 0.0783 (8) | |
H14 | 0.4681 | 0.9425 | 0.6795 | 0.094* | |
C15 | 0.4771 (2) | 0.7040 (6) | 0.75619 (15) | 0.0832 (9) | |
H15 | 0.5344 | 0.7804 | 0.7865 | 0.100* | |
C16 | 0.4325 (2) | 0.4969 (6) | 0.77479 (12) | 0.0802 (8) | |
H16 | 0.4596 | 0.4313 | 0.8178 | 0.096* | |
C17 | 0.34734 (19) | 0.3830 (5) | 0.73023 (10) | 0.0619 (6) | |
H17 | 0.3174 | 0.2409 | 0.7434 | 0.074* | |
N1 | 0.26556 (13) | 0.1739 (3) | 0.52914 (8) | 0.0460 (4) | |
N2 | 0.21010 (12) | 0.3551 (3) | 0.54916 (7) | 0.0435 (4) | |
O1 | 0.07681 (11) | 0.7942 (3) | 0.55347 (7) | 0.0529 (4) | |
O2 | 0.04902 (11) | 0.8197 (3) | 0.44201 (6) | 0.0549 (4) | |
H2A | 0.0087 | 0.9321 | 0.4460 | 0.082* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0844 (17) | 0.0574 (15) | 0.0805 (17) | 0.0054 (14) | 0.0421 (15) | −0.0104 (13) |
C2 | 0.0992 (19) | 0.0666 (17) | 0.0541 (14) | 0.0088 (15) | 0.0267 (13) | −0.0071 (12) |
C3 | 0.0759 (14) | 0.0518 (13) | 0.0475 (12) | 0.0096 (12) | 0.0173 (11) | −0.0001 (10) |
C4 | 0.0517 (11) | 0.0373 (11) | 0.0472 (11) | −0.0058 (9) | 0.0178 (9) | −0.0008 (9) |
C5 | 0.0554 (12) | 0.0594 (14) | 0.0533 (12) | 0.0028 (11) | 0.0153 (10) | 0.0005 (10) |
C6 | 0.0659 (14) | 0.0633 (15) | 0.0732 (16) | 0.0148 (13) | 0.0246 (12) | 0.0009 (13) |
C7 | 0.0462 (10) | 0.0361 (10) | 0.0402 (10) | −0.0043 (9) | 0.0105 (8) | 0.0014 (8) |
C8 | 0.0501 (10) | 0.0440 (11) | 0.0376 (10) | −0.0045 (10) | 0.0100 (8) | 0.0013 (8) |
C9 | 0.0418 (9) | 0.0384 (10) | 0.0408 (10) | −0.0021 (9) | 0.0098 (8) | 0.0023 (8) |
C10 | 0.0389 (9) | 0.0429 (11) | 0.0427 (10) | −0.0034 (9) | 0.0095 (8) | 0.0027 (8) |
C11 | 0.0578 (11) | 0.0491 (12) | 0.0408 (10) | 0.0025 (10) | 0.0181 (9) | 0.0072 (9) |
C12 | 0.0515 (11) | 0.0426 (11) | 0.0390 (10) | 0.0077 (9) | 0.0143 (8) | −0.0036 (8) |
C13 | 0.0624 (13) | 0.0492 (13) | 0.0620 (14) | 0.0024 (11) | 0.0111 (11) | 0.0015 (11) |
C14 | 0.0727 (16) | 0.0616 (16) | 0.097 (2) | −0.0076 (14) | 0.0183 (15) | −0.0156 (15) |
C15 | 0.0659 (15) | 0.095 (2) | 0.0775 (19) | 0.0039 (16) | 0.0020 (14) | −0.0396 (17) |
C16 | 0.0821 (18) | 0.104 (2) | 0.0454 (13) | 0.0168 (18) | 0.0029 (12) | −0.0116 (14) |
C17 | 0.0740 (14) | 0.0721 (16) | 0.0393 (11) | 0.0113 (13) | 0.0153 (10) | 0.0048 (11) |
N1 | 0.0536 (9) | 0.0406 (9) | 0.0444 (9) | 0.0036 (8) | 0.0144 (7) | 0.0027 (7) |
N2 | 0.0502 (9) | 0.0431 (9) | 0.0380 (8) | 0.0003 (8) | 0.0136 (7) | 0.0027 (7) |
O1 | 0.0580 (8) | 0.0570 (9) | 0.0442 (8) | 0.0094 (7) | 0.0151 (7) | 0.0011 (7) |
O2 | 0.0626 (9) | 0.0545 (9) | 0.0446 (8) | 0.0145 (7) | 0.0098 (7) | 0.0037 (6) |
C1—C2 | 1.365 (3) | C10—O2 | 1.311 (2) |
C1—C6 | 1.370 (3) | C11—N2 | 1.465 (2) |
C1—H1 | 0.9300 | C11—C12 | 1.506 (3) |
C2—C3 | 1.381 (3) | C11—H11A | 0.9700 |
C2—H2 | 0.9300 | C11—H11B | 0.9700 |
C3—C4 | 1.384 (3) | C12—C13 | 1.378 (3) |
C3—H3 | 0.9300 | C12—C17 | 1.380 (3) |
C4—C5 | 1.385 (3) | C13—C14 | 1.383 (3) |
C4—C7 | 1.474 (3) | C13—H13 | 0.9300 |
C5—C6 | 1.381 (3) | C14—C15 | 1.378 (4) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—H6 | 0.9300 | C15—C16 | 1.356 (4) |
C7—N1 | 1.336 (2) | C15—H15 | 0.9300 |
C7—C8 | 1.393 (3) | C16—C17 | 1.379 (3) |
C8—C9 | 1.370 (2) | C16—H16 | 0.9300 |
C8—H8 | 0.9300 | C17—H17 | 0.9300 |
C9—N2 | 1.363 (2) | N1—N2 | 1.345 (2) |
C9—C10 | 1.465 (3) | O2—H2A | 0.8200 |
C10—O1 | 1.223 (2) | ||
C2—C1—C6 | 119.7 (2) | N2—C11—C12 | 113.68 (15) |
C2—C1—H1 | 120.2 | N2—C11—H11A | 108.8 |
C6—C1—H1 | 120.2 | C12—C11—H11A | 108.8 |
C1—C2—C3 | 120.5 (2) | N2—C11—H11B | 108.8 |
C1—C2—H2 | 119.8 | C12—C11—H11B | 108.8 |
C3—C2—H2 | 119.8 | H11A—C11—H11B | 107.7 |
C2—C3—C4 | 120.5 (2) | C13—C12—C17 | 118.9 (2) |
C2—C3—H3 | 119.7 | C13—C12—C11 | 121.73 (18) |
C4—C3—H3 | 119.7 | C17—C12—C11 | 119.29 (19) |
C3—C4—C5 | 118.38 (19) | C12—C13—C14 | 120.2 (2) |
C3—C4—C7 | 120.05 (18) | C12—C13—H13 | 119.9 |
C5—C4—C7 | 121.55 (18) | C14—C13—H13 | 119.9 |
C6—C5—C4 | 120.5 (2) | C15—C14—C13 | 120.1 (3) |
C6—C5—H5 | 119.7 | C15—C14—H14 | 119.9 |
C4—C5—H5 | 119.7 | C13—C14—H14 | 119.9 |
C1—C6—C5 | 120.4 (2) | C16—C15—C14 | 119.9 (3) |
C1—C6—H6 | 119.8 | C16—C15—H15 | 120.1 |
C5—C6—H6 | 119.8 | C14—C15—H15 | 120.1 |
N1—C7—C8 | 110.35 (16) | C15—C16—C17 | 120.4 (3) |
N1—C7—C4 | 120.34 (17) | C15—C16—H16 | 119.8 |
C8—C7—C4 | 129.27 (17) | C17—C16—H16 | 119.8 |
C9—C8—C7 | 105.97 (16) | C16—C17—C12 | 120.5 (2) |
C9—C8—H8 | 127.0 | C16—C17—H17 | 119.7 |
C7—C8—H8 | 127.0 | C12—C17—H17 | 119.7 |
N2—C9—C8 | 106.46 (16) | C7—N1—N2 | 105.94 (15) |
N2—C9—C10 | 125.21 (16) | N1—N2—C9 | 111.28 (14) |
C8—C9—C10 | 128.33 (17) | N1—N2—C11 | 117.94 (15) |
O1—C10—O2 | 123.60 (18) | C9—N2—C11 | 130.75 (16) |
O1—C10—C9 | 124.37 (17) | C10—O2—H2A | 109.5 |
O2—C10—C9 | 112.02 (16) | ||
C6—C1—C2—C3 | 0.5 (4) | N2—C11—C12—C13 | 38.8 (3) |
C1—C2—C3—C4 | −0.5 (4) | N2—C11—C12—C17 | −144.13 (18) |
C2—C3—C4—C5 | 0.0 (3) | C17—C12—C13—C14 | −0.2 (3) |
C2—C3—C4—C7 | −178.3 (2) | C11—C12—C13—C14 | 176.9 (2) |
C3—C4—C5—C6 | 0.4 (3) | C12—C13—C14—C15 | −0.1 (4) |
C7—C4—C5—C6 | 178.70 (19) | C13—C14—C15—C16 | 0.3 (4) |
C2—C1—C6—C5 | −0.1 (4) | C14—C15—C16—C17 | −0.2 (4) |
C4—C5—C6—C1 | −0.4 (4) | C15—C16—C17—C12 | −0.2 (4) |
C3—C4—C7—N1 | 159.65 (19) | C13—C12—C17—C16 | 0.4 (3) |
C5—C4—C7—N1 | −18.6 (3) | C11—C12—C17—C16 | −176.8 (2) |
C3—C4—C7—C8 | −17.8 (3) | C8—C7—N1—N2 | 0.4 (2) |
C5—C4—C7—C8 | 163.97 (19) | C4—C7—N1—N2 | −177.49 (16) |
N1—C7—C8—C9 | −0.4 (2) | C7—N1—N2—C9 | −0.3 (2) |
C4—C7—C8—C9 | 177.26 (18) | C7—N1—N2—C11 | 178.09 (16) |
C7—C8—C9—N2 | 0.2 (2) | C8—C9—N2—N1 | 0.0 (2) |
C7—C8—C9—C10 | −179.40 (17) | C10—C9—N2—N1 | 179.64 (16) |
N2—C9—C10—O1 | 3.0 (3) | C8—C9—N2—C11 | −178.03 (18) |
C8—C9—C10—O1 | −177.48 (19) | C10—C9—N2—C11 | 1.6 (3) |
N2—C9—C10—O2 | −175.67 (17) | C12—C11—N2—N1 | 81.3 (2) |
C8—C9—C10—O2 | 3.9 (3) | C12—C11—N2—C9 | −100.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.85 | 2.662 (2) | 173 |
Symmetry code: (i) −x, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H14N2O2 |
Mr | 278.30 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 13.1764 (5), 5.3356 (2), 20.6646 (7) |
β (°) | 106.132 (3) |
V (Å3) | 1395.60 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.21 × 0.17 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (APEX2; Bruker, 2005) |
Tmin, Tmax | 0.974, 0.985 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8816, 3175, 1921 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.164, 0.90 |
No. of reflections | 3175 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.19 |
Computer programs: APEX2 (Bruker, 2005), APEX2, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1i | 0.82 | 1.85 | 2.662 (2) | 172.9 |
Symmetry code: (i) −x, −y+2, −z+1. |
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Pyrazole moiety plays an essential role in biologically active compounds. Many pyrazole derivatives are known to exhibit a wide range of biological properties such as anticoagulant (Jia et al., 2004), antipyretic, antibacterial, hypoglycaemic, antihyperglycaemic, analgesic, anti-inflammatory, sedative-hypnotic (Cottineau et al., 2002; Finn et al., 2003), and antitumour (Wei et al., 2006) activities. We report here the crystal structure of the title compound (I).