Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705903X/sg2207sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705903X/sg2207Isup2.hkl |
CCDC reference: 665042
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (Wav) = 0.000 Å
- R factor = 0.041
- wR factor = 0.114
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 2038 Count of symmetry unique reflns 1082 Completeness (_total/calc) 188.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 956 Fraction of Friedel pairs measured 0.884 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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: Liao et al. (2000); Elguero et al. (1984); Fun et al. (1996); Lu et al. (1996); Kai et al. (2007).
A solution of 3-chloro-6-hydrazinylpicolinic acid(10 mmol) in 50 ml toluene was added to a solution of pentane-2,4-dione(10 mmol) in 10 ml toluene. The reaction mixture was refluxed for 1 h with stirring. then the resulting pale colorless precipitate was obtained by filtration, washed several times with ethanol and dried in vacuo (yield 90%). Analysis calculated for the title compound (C11H10ClN3O2): C, 52.40; H, 4.11; N, 16.60; O, 12.81; in the crystal, found: C, 52.50; H, 4.01; N, 16.70; O, 12.71. A me thanol solution of the title compound was slowly evaporated and colorless crystals were obtained after one week.
The positions of all H atoms were fixed geometrically and refined isotropically using a riding model. The bond lengths for C—H are in the range 0.93–0.96 Å, The bond lengths for N—H are 0.86 Å, respectively.
Data collection: Bruker SMART(Siemens, 1996); cell refinement: Bruker SMART(Siemens, 1996); data reduction: Bruker SAINT(Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
C11H10ClN3O2 | F(000) = 520 |
Mr = 251.67 | Dx = 1.426 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2331 reflections |
a = 17.972 (2) Å | θ = 2.3–27.0° |
b = 4.5618 (6) Å | µ = 0.32 mm−1 |
c = 14.303 (2) Å | T = 298 K |
V = 1172.6 (3) Å3 | Block, colorless |
Z = 4 | 0.53 × 0.50 × 0.36 mm |
Bruker SMART CCD area-detector diffractometer | 2038 independent reflections |
Radiation source: fine-focus sealed tube | 1806 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
phi and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −21→16 |
Tmin = 0.849, Tmax = 0.894 | k = −3→5 |
4435 measured reflections | l = −17→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.0549P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2038 reflections | Δρmax = 0.25 e Å−3 |
154 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 956 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (9) |
C11H10ClN3O2 | V = 1172.6 (3) Å3 |
Mr = 251.67 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 17.972 (2) Å | µ = 0.32 mm−1 |
b = 4.5618 (6) Å | T = 298 K |
c = 14.303 (2) Å | 0.53 × 0.50 × 0.36 mm |
Bruker SMART CCD area-detector diffractometer | 2038 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1806 reflections with I > 2σ(I) |
Tmin = 0.849, Tmax = 0.894 | Rint = 0.041 |
4435 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.114 | Δρmax = 0.25 e Å−3 |
S = 1.06 | Δρmin = −0.24 e Å−3 |
2038 reflections | Absolute structure: Flack (1983), 956 Friedel pairs |
154 parameters | Absolute structure parameter: −0.03 (9) |
1 restraint |
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 | ||
Cl1 | −0.15772 (4) | 1.09661 (17) | 0.51407 (7) | 0.0586 (3) | |
N1 | 0.00189 (14) | 0.5293 (6) | 0.44703 (17) | 0.0400 (6) | |
N2 | 0.09799 (11) | 0.3047 (5) | 0.52919 (16) | 0.0376 (5) | |
N3 | 0.12733 (14) | 0.2224 (6) | 0.61406 (17) | 0.0405 (6) | |
O1 | −0.05743 (12) | 0.7992 (6) | 0.28282 (15) | 0.0593 (6) | |
H1 | −0.0786 | 0.7646 | 0.2332 | 0.089* | |
O2 | −0.16318 (15) | 0.6490 (8) | 0.3462 (2) | 0.0877 (11) | |
C1 | −0.09889 (17) | 0.7136 (8) | 0.3518 (2) | 0.0500 (8) | |
C2 | −0.05762 (17) | 0.7100 (7) | 0.4443 (2) | 0.0410 (7) | |
C3 | −0.08141 (15) | 0.8661 (6) | 0.5207 (2) | 0.0396 (6) | |
C4 | −0.04237 (18) | 0.8392 (7) | 0.6036 (2) | 0.0461 (8) | |
H4 | −0.0570 | 0.9460 | 0.6559 | 0.055* | |
C5 | 0.01755 (17) | 0.6565 (7) | 0.6090 (2) | 0.0414 (7) | |
H5 | 0.0442 | 0.6354 | 0.6643 | 0.050* | |
C6 | 0.03751 (14) | 0.5019 (6) | 0.5282 (2) | 0.0361 (6) | |
C7 | 0.1212 (2) | 0.2198 (11) | 0.3557 (2) | 0.0657 (10) | |
H7A | 0.1556 | 0.1052 | 0.3197 | 0.099* | |
H7B | 0.1269 | 0.4233 | 0.3402 | 0.099* | |
H7C | 0.0713 | 0.1588 | 0.3417 | 0.099* | |
C8 | 0.13615 (16) | 0.1764 (8) | 0.4570 (2) | 0.0418 (7) | |
C9 | 0.19019 (16) | 0.0079 (7) | 0.4978 (2) | 0.0450 (7) | |
H9 | 0.2252 | −0.1074 | 0.4671 | 0.054* | |
C10 | 0.18273 (18) | 0.0425 (7) | 0.5939 (2) | 0.0431 (7) | |
C11 | 0.22903 (18) | −0.0922 (8) | 0.6711 (3) | 0.0571 (9) | |
H11A | 0.2222 | 0.0176 | 0.7277 | 0.086* | |
H11B | 0.2806 | −0.0882 | 0.6536 | 0.086* | |
H11C | 0.2137 | −0.2914 | 0.6809 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0498 (4) | 0.0487 (4) | 0.0773 (6) | 0.0094 (3) | 0.0004 (4) | 0.0100 (4) |
N1 | 0.0391 (12) | 0.0466 (13) | 0.0342 (14) | −0.0025 (11) | −0.0008 (10) | 0.0018 (12) |
N2 | 0.0365 (12) | 0.0461 (12) | 0.0303 (12) | −0.0009 (10) | 0.0001 (10) | 0.0017 (12) |
N3 | 0.0390 (13) | 0.0494 (15) | 0.0330 (13) | 0.0017 (11) | −0.0002 (9) | 0.0009 (12) |
O1 | 0.0504 (13) | 0.0890 (18) | 0.0384 (12) | 0.0002 (12) | −0.0020 (10) | 0.0052 (12) |
O2 | 0.0599 (16) | 0.142 (3) | 0.0611 (17) | −0.0352 (16) | −0.0180 (12) | 0.0307 (18) |
C1 | 0.048 (2) | 0.054 (2) | 0.0485 (19) | −0.0010 (15) | −0.0042 (14) | 0.0097 (15) |
C2 | 0.0392 (16) | 0.0421 (16) | 0.0416 (16) | −0.0075 (13) | −0.0031 (12) | 0.0097 (14) |
C3 | 0.0392 (13) | 0.0344 (14) | 0.0452 (16) | −0.0036 (11) | 0.0002 (14) | 0.0071 (14) |
C4 | 0.0546 (19) | 0.0421 (16) | 0.0414 (18) | 0.0020 (14) | 0.0058 (14) | 0.0003 (13) |
C5 | 0.0486 (17) | 0.0419 (15) | 0.0336 (16) | −0.0007 (14) | −0.0038 (12) | −0.0001 (12) |
C6 | 0.0395 (13) | 0.0357 (13) | 0.0331 (14) | −0.0068 (11) | 0.0002 (12) | 0.0038 (13) |
C7 | 0.067 (2) | 0.092 (3) | 0.0384 (19) | 0.015 (2) | 0.0096 (16) | −0.0034 (18) |
C8 | 0.0377 (15) | 0.0524 (18) | 0.0352 (16) | −0.0034 (14) | 0.0059 (12) | −0.0008 (14) |
C9 | 0.0348 (15) | 0.0531 (18) | 0.0472 (19) | 0.0001 (13) | 0.0069 (12) | −0.0063 (15) |
C10 | 0.0376 (16) | 0.0455 (16) | 0.0462 (18) | −0.0023 (14) | 0.0018 (13) | 0.0018 (15) |
C11 | 0.050 (2) | 0.066 (2) | 0.055 (2) | 0.0165 (16) | −0.0034 (15) | −0.0003 (17) |
Cl1—C3 | 1.731 (3) | C4—H4 | 0.9300 |
N1—C6 | 1.332 (4) | C5—C6 | 1.401 (4) |
N1—C2 | 1.351 (4) | C5—H5 | 0.9300 |
N2—C8 | 1.371 (4) | C7—C8 | 1.487 (5) |
N2—N3 | 1.376 (3) | C7—H7A | 0.9600 |
N2—C6 | 1.411 (3) | C7—H7B | 0.9600 |
N3—C10 | 1.322 (4) | C7—H7C | 0.9600 |
O1—C1 | 1.297 (4) | C8—C9 | 1.369 (5) |
O1—H1 | 0.8200 | C9—C10 | 1.390 (5) |
O2—C1 | 1.195 (4) | C9—H9 | 0.9300 |
C1—C2 | 1.516 (4) | C10—C11 | 1.513 (5) |
C2—C3 | 1.374 (4) | C11—H11A | 0.9600 |
C3—C4 | 1.383 (5) | C11—H11B | 0.9600 |
C4—C5 | 1.364 (4) | C11—H11C | 0.9600 |
C6—N1—C2 | 117.6 (3) | C5—C6—N2 | 120.7 (2) |
C8—N2—N3 | 110.9 (2) | C8—C7—H7A | 109.5 |
C8—N2—C6 | 130.5 (3) | C8—C7—H7B | 109.5 |
N3—N2—C6 | 118.6 (2) | H7A—C7—H7B | 109.5 |
C10—N3—N2 | 105.4 (2) | C8—C7—H7C | 109.5 |
C1—O1—H1 | 109.5 | H7A—C7—H7C | 109.5 |
O2—C1—O1 | 125.4 (3) | H7B—C7—H7C | 109.5 |
O2—C1—C2 | 121.9 (3) | C9—C8—N2 | 105.8 (3) |
O1—C1—C2 | 112.7 (3) | C9—C8—C7 | 128.2 (3) |
N1—C2—C3 | 122.6 (3) | N2—C8—C7 | 125.9 (3) |
N1—C2—C1 | 114.8 (3) | C8—C9—C10 | 106.8 (3) |
C3—C2—C1 | 122.5 (3) | C8—C9—H9 | 126.6 |
C2—C3—C4 | 118.6 (3) | C10—C9—H9 | 126.6 |
C2—C3—Cl1 | 121.2 (2) | N3—C10—C9 | 111.0 (3) |
C4—C3—Cl1 | 120.2 (2) | N3—C10—C11 | 120.5 (3) |
C5—C4—C3 | 120.2 (3) | C9—C10—C11 | 128.5 (3) |
C5—C4—H4 | 119.9 | C10—C11—H11A | 109.5 |
C3—C4—H4 | 119.9 | C10—C11—H11B | 109.5 |
C4—C5—C6 | 117.6 (3) | H11A—C11—H11B | 109.5 |
C4—C5—H5 | 121.2 | C10—C11—H11C | 109.5 |
C6—C5—H5 | 121.2 | H11A—C11—H11C | 109.5 |
N1—C6—C5 | 123.3 (3) | H11B—C11—H11C | 109.5 |
N1—C6—N2 | 116.0 (2) | ||
C8—N2—N3—C10 | −0.5 (3) | C4—C5—C6—N1 | 1.3 (4) |
C6—N2—N3—C10 | −179.4 (2) | C4—C5—C6—N2 | −178.7 (2) |
C6—N1—C2—C3 | 0.9 (4) | C8—N2—C6—N1 | 14.4 (4) |
C6—N1—C2—C1 | −175.7 (2) | N3—N2—C6—N1 | −167.1 (2) |
O2—C1—C2—N1 | 120.9 (4) | C8—N2—C6—C5 | −165.6 (3) |
O1—C1—C2—N1 | −60.7 (4) | N3—N2—C6—C5 | 12.9 (4) |
O2—C1—C2—C3 | −55.7 (5) | N3—N2—C8—C9 | 0.5 (3) |
O1—C1—C2—C3 | 122.8 (3) | C6—N2—C8—C9 | 179.1 (3) |
N1—C2—C3—C4 | 0.7 (4) | N3—N2—C8—C7 | −178.6 (4) |
C1—C2—C3—C4 | 176.9 (3) | C6—N2—C8—C7 | 0.0 (5) |
N1—C2—C3—Cl1 | 179.7 (2) | N2—C8—C9—C10 | −0.3 (4) |
C1—C2—C3—Cl1 | −4.0 (4) | C7—C8—C9—C10 | 178.8 (4) |
C2—C3—C4—C5 | −1.2 (4) | N2—N3—C10—C9 | 0.4 (4) |
Cl1—C3—C4—C5 | 179.7 (2) | N2—N3—C10—C11 | 179.5 (3) |
C3—C4—C5—C6 | 0.3 (4) | C8—C9—C10—N3 | −0.1 (4) |
C2—N1—C6—C5 | −1.9 (4) | C8—C9—C10—C11 | −179.2 (3) |
C2—N1—C6—N2 | 178.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N3i | 0.82 | 1.92 | 2.723 (3) | 167 |
Symmetry code: (i) −x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H10ClN3O2 |
Mr | 251.67 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 298 |
a, b, c (Å) | 17.972 (2), 4.5618 (6), 14.303 (2) |
V (Å3) | 1172.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.53 × 0.50 × 0.36 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.849, 0.894 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4435, 2038, 1806 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.114, 1.06 |
No. of reflections | 2038 |
No. of parameters | 154 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.25, −0.24 |
Absolute structure | Flack (1983), 956 Friedel pairs |
Absolute structure parameter | −0.03 (9) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N3i | 0.82 | 1.92 | 2.723 (3) | 167 |
Symmetry code: (i) −x, −y+1, z−1/2. |
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The chemical and pharmacological properties of pyrazoles have been investigated extensively, owing to their chelating ability with metal ions and to their potentially beneficial chemical and biological activities, (Elguero et al., 1984;), e.g; antitumor, antineoplastic,antibacterial and antimalarial (Liao et al.,2000; Fun et al.,1996; Lu et al.,1996). Recently we reported the 4-(3,5-dimethyl-1H-pyrazol-1-yl)phthalazin-1(2H)-one; (Kai et al., 2007). We report here the synthesis and crystal structure of 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid. The C—N distances range from 1.332 (4) to 1.411 (3) Å, i.e. normal values. The C=O bond length is 1.231 (3) Å, indicating that the molecule is in the keto form.
In the crystal structure, the molecules are interconnected, by intermolecular O—H···O hydrogen bonds (Fig. 2; for symmetry codes see Table1).