3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid–triphenyl­phosphine oxide (1/1)

Hu, F.-L.; Huang, Z.-J.; Zhang, S.-S.; Zhuang, Y.; Luo, W.-Q.

doi:10.1107/S160053680802045X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1427

doi:10.1107/S160053680802045X

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3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid–triphenylphosphine oxide (1/1)

Fei-Long Hu,^a Zhong-Jing Huang,^a ^* Shan-Shan Zhang,^a Yue Zhuang ^a and Wei-Qiang Luo ^a

^aCollege of Chemistry and Ecological Engineering, Guangxi University for Nationalities, Nanning 530006, People's Republic of China
^*Correspondence e-mail: yxhphd@163.com

(Received 1 July 2008; accepted 3 July 2008; online 9 July 2008)

In the title 1:1 adduct, C₁₁H₁₀ClN₃O₂·C₁₈H₁₅OP, the dihedral angle between the pyridine and pyrazole rings is 10.3 (2)°. The two components of the adduct are linked by an O—H⋯O hydrogen bond.

Related literature

For background, see: Mann et al. (1992 ).

Experimental

Crystal data

C₁₁H₁₀ClN₃O₂·C₁₈H₁₅OP
M_r = 529.94
Monoclinic, P 2₁ /c
a = 16.6694 (14) Å
b = 9.8176 (11) Å
c = 18.272 (2) Å
β = 116.089 (2)°
V = 2685.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 (2) K
0.23 × 0.18 × 0.09 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.947, T_max = 0.979
13279 measured reflections
4721 independent reflections
2333 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.083
S = 1.03
4721 reflections
337 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.79	1.76	2.537 (2)	165

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802045X/hb2757sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802045X/hb2757Isup2.hkl

checkCIF report

Comment top

Pyrazoles have been investigated extensively, owing to their chelating ability with metal ions and their potentially beneficial biological activities (e.g. Mann et al., 1992). As part of our studies on these compounds, we report here the synthesis and crystal structure of the title compound, (I), (Fig. 1).

In the 3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid molecule, the dihedral angle between the two ring mean planes is 10.3 (2) °. The two components of the adduct interact by way of an O—H···O hydrogen bond (Table 1).

Related literature top

For background, see: Mann et al. (1992).

Experimental top

3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 251.04 mg) was dissolved in distilled water (15 ml) and triphenylphosphine oxide (0.5 mmol, 139.04 mg) in distilled water (5 ml) was added with stirring at 323 K. The resulting solution was allowed to react for 5 h and was then filtered. Colourless blocks of (I) were obtained by slow evaporation of a water solution over a period of one month (yield 75%). Elemental analysis: found: C 65.71; H 4.73; N 7.94; O 9.06%. calc. for C₂₉H₂₅ClN₃O₃P: C 65.72; H 4.75; N 7.93; O 9.06%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms. The hydrogen bond is indicated by a double-dashed line.

3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid–triphenylphosphine oxide (1/1) top

Crystal data top

C₁₁H₁₀ClN₃O₂·C₁₈H₁₅OP	F(000) = 1104
M_r = 529.94	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2022 reflections
a = 16.6694 (14) Å	θ = 2.3–25.2°
b = 9.8176 (11) Å	µ = 0.24 mm⁻¹
c = 18.272 (2) Å	T = 298 K
β = 116.089 (2)°	Block, colourless
V = 2685.7 (5) Å³	0.23 × 0.18 × 0.09 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	4721 independent reflections
Radiation source: fine-focus sealed tube	2333 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.947, T_max = 0.979	k = −11→11
13279 measured reflections	l = −11→21

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0142P)²] where P = (F_o² + 2F_c²)/3
4721 reflections	(Δ/σ)_max = 0.001
337 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₁H₁₀ClN₃O₂·C₁₈H₁₅OP	V = 2685.7 (5) Å³
M_r = 529.94	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.6694 (14) Å	µ = 0.24 mm⁻¹
b = 9.8176 (11) Å	T = 298 K
c = 18.272 (2) Å	0.23 × 0.18 × 0.09 mm
β = 116.089 (2)°

Data collection top

Bruker SMART CCD diffractometer	4721 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2333 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.979	R_int = 0.063
13279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.18 e Å⁻³
4721 reflections	Δρ_min = −0.27 e Å⁻³
337 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
P1	0.12197 (5)	0.76008 (8)	0.14024 (4)	0.0528 (2)
O3	0.16936 (11)	0.88630 (18)	0.18229 (10)	0.0645 (5)
C12	0.18622 (17)	0.6094 (3)	0.18123 (18)	0.0533 (7)
C13	0.24643 (19)	0.6082 (3)	0.2624 (2)	0.0723 (9)
H13	0.2538	0.6855	0.2941	0.087*
C14	0.2960 (2)	0.4923 (4)	0.2970 (2)	0.0887 (11)
H14	0.3359	0.4920	0.3520	0.106*
C15	0.2869 (2)	0.3793 (4)	0.2513 (3)	0.0828 (11)
H15	0.3216	0.3027	0.2745	0.099*
C16	0.2266 (2)	0.3784 (3)	0.1711 (2)	0.0783 (10)
H16	0.2190	0.3003	0.1400	0.094*
C17	0.17677 (19)	0.4932 (3)	0.13616 (18)	0.0683 (9)
H17	0.1362	0.4919	0.0813	0.082*
C18	0.01884 (17)	0.7409 (3)	0.14774 (15)	0.0504 (7)
C19	−0.0251 (2)	0.6190 (3)	0.13663 (17)	0.0683 (9)
H19	−0.0013	0.5412	0.1247	0.082*
C20	−0.1048 (2)	0.6108 (3)	0.14302 (19)	0.0800 (10)
H20	−0.1339	0.5277	0.1362	0.096*
C21	−0.1400 (2)	0.7247 (4)	0.15932 (19)	0.0793 (10)
H21	−0.1939	0.7193	0.1627	0.095*
C22	−0.0977 (2)	0.8459 (4)	0.1707 (2)	0.0884 (11)
H22	−0.1224	0.9235	0.1818	0.106*
C23	−0.0169 (2)	0.8536 (3)	0.16571 (18)	0.0732 (9)
H23	0.0130	0.9364	0.1747	0.088*
C24	0.09431 (19)	0.7625 (3)	0.03445 (16)	0.0542 (7)
C25	0.16220 (19)	0.7500 (3)	0.01058 (19)	0.0682 (9)
H25	0.2203	0.7338	0.0496	0.082*
C26	0.1448 (2)	0.7614 (3)	−0.0703 (2)	0.0781 (9)
H26	0.1909	0.7529	−0.0857	0.094*
C27	0.0600 (3)	0.7849 (3)	−0.1274 (2)	0.0841 (11)
H27	0.0482	0.7926	−0.1819	0.101*
C28	−0.0077 (2)	0.7974 (3)	−0.1057 (2)	0.0905 (12)
H28	−0.0655	0.8133	−0.1453	0.109*
C29	0.0090 (2)	0.7866 (3)	−0.02499 (19)	0.0721 (9)
H29	−0.0378	0.7956	−0.0106	0.086*
O1	0.29030 (12)	1.0307 (2)	0.28946 (12)	0.0745 (6)
H1	0.2471	0.9901	0.2595	0.112*
C1	0.32200 (18)	0.9910 (3)	0.36492 (19)	0.0551 (8)
O2	0.29977 (14)	0.8882 (2)	0.38566 (13)	0.0925 (7)
C2	0.38830 (17)	1.0884 (3)	0.42273 (18)	0.0496 (7)
N1	0.43821 (15)	1.1548 (2)	0.39350 (13)	0.0558 (6)
C3	0.39748 (18)	1.1108 (3)	0.49982 (19)	0.0620 (8)
Cl1	0.33173 (5)	1.03306 (10)	0.53878 (5)	0.0911 (3)
C4	0.4605 (2)	1.2043 (4)	0.5487 (2)	0.0834 (11)
H4A	0.4674	1.2218	0.6011	0.100*
C6	0.49929 (19)	1.2413 (3)	0.4415 (2)	0.0610 (8)
N2	0.55065 (16)	1.3065 (3)	0.4085 (2)	0.0720 (8)
C5	0.5116 (2)	1.2697 (3)	0.5199 (2)	0.0819 (10)
H5A	0.5542	1.3326	0.5521	0.098*
N3	0.60429 (19)	1.4127 (3)	0.45224 (19)	0.0929 (10)
C8	0.5594 (2)	1.2799 (4)	0.3382 (3)	0.0800 (11)
C7	0.5137 (2)	1.1695 (4)	0.27913 (19)	0.0996 (12)
H7A	0.5310	1.1728	0.2355	0.149*
H7B	0.4502	1.1812	0.2574	0.149*
H7C	0.5302	1.0830	0.3061	0.149*
C9	0.6186 (3)	1.3730 (5)	0.3377 (3)	0.1022 (15)
H9	0.638 (2)	1.383 (4)	0.298 (2)	0.123*
C10	0.6447 (2)	1.4513 (4)	0.4071 (3)	0.0998 (15)
C11	0.7108 (2)	1.5670 (4)	0.4364 (3)	0.1496 (18)
H11A	0.7145	1.6011	0.4871	0.224*
H11B	0.6915	1.6386	0.3966	0.224*
H11C	0.7685	1.5349	0.4443	0.224*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0495 (5)	0.0512 (5)	0.0563 (5)	0.0002 (4)	0.0221 (4)	−0.0042 (4)
O3	0.0573 (12)	0.0545 (13)	0.0719 (13)	−0.0055 (11)	0.0194 (10)	−0.0128 (10)
C12	0.0508 (19)	0.051 (2)	0.060 (2)	0.0008 (15)	0.0264 (17)	−0.0001 (16)
C13	0.070 (2)	0.061 (2)	0.075 (2)	−0.0039 (19)	0.023 (2)	0.0053 (19)
C14	0.073 (3)	0.078 (3)	0.091 (3)	−0.002 (2)	0.013 (2)	0.023 (2)
C15	0.067 (2)	0.067 (3)	0.115 (3)	0.013 (2)	0.039 (2)	0.026 (2)
C16	0.085 (3)	0.059 (3)	0.106 (3)	0.012 (2)	0.056 (2)	0.001 (2)
C17	0.071 (2)	0.061 (2)	0.075 (2)	0.0125 (19)	0.0339 (19)	0.002 (2)
C18	0.0521 (17)	0.0464 (19)	0.0552 (17)	−0.0014 (17)	0.0259 (14)	−0.0045 (16)
C19	0.066 (2)	0.060 (2)	0.088 (2)	−0.0017 (18)	0.0424 (19)	−0.0111 (18)
C20	0.071 (2)	0.066 (3)	0.112 (3)	−0.010 (2)	0.049 (2)	−0.009 (2)
C21	0.063 (2)	0.080 (3)	0.106 (3)	−0.001 (2)	0.048 (2)	−0.004 (2)
C22	0.079 (3)	0.071 (3)	0.134 (3)	0.010 (2)	0.064 (2)	−0.011 (2)
C23	0.070 (2)	0.056 (2)	0.106 (3)	−0.0042 (19)	0.050 (2)	−0.007 (2)
C24	0.0568 (19)	0.0489 (19)	0.0603 (19)	−0.0006 (17)	0.0288 (17)	−0.0004 (16)
C25	0.069 (2)	0.071 (2)	0.072 (2)	0.0076 (19)	0.0368 (18)	0.0017 (19)
C26	0.099 (3)	0.073 (2)	0.083 (3)	0.010 (2)	0.059 (2)	0.003 (2)
C27	0.114 (3)	0.082 (3)	0.063 (2)	−0.008 (2)	0.044 (3)	0.0024 (19)
C28	0.081 (3)	0.118 (3)	0.063 (3)	−0.008 (2)	0.024 (2)	0.019 (2)
C29	0.063 (2)	0.088 (3)	0.067 (2)	0.0002 (19)	0.0297 (19)	0.0139 (18)
O1	0.0828 (15)	0.0717 (15)	0.0631 (14)	−0.0256 (12)	0.0267 (12)	−0.0080 (12)
C1	0.053 (2)	0.054 (2)	0.064 (2)	−0.0020 (17)	0.0309 (18)	0.0027 (19)
O2	0.1069 (18)	0.0782 (18)	0.0849 (16)	−0.0368 (15)	0.0353 (13)	0.0044 (14)
C2	0.0451 (18)	0.0485 (19)	0.055 (2)	−0.0011 (15)	0.0213 (16)	0.0003 (15)
N1	0.0491 (15)	0.0534 (17)	0.0658 (17)	−0.0057 (13)	0.0262 (14)	0.0016 (13)
C3	0.055 (2)	0.072 (2)	0.062 (2)	−0.0038 (18)	0.0289 (17)	0.0020 (18)
Cl1	0.0865 (6)	0.1195 (8)	0.0837 (6)	−0.0107 (6)	0.0526 (5)	0.0067 (5)
C4	0.076 (2)	0.103 (3)	0.069 (2)	−0.014 (2)	0.030 (2)	−0.018 (2)
C6	0.0494 (19)	0.054 (2)	0.076 (2)	−0.0038 (17)	0.0248 (18)	0.005 (2)
N2	0.0549 (17)	0.061 (2)	0.098 (2)	−0.0123 (14)	0.0318 (17)	0.0078 (17)
C5	0.069 (2)	0.085 (3)	0.085 (3)	−0.023 (2)	0.027 (2)	−0.023 (2)
N3	0.067 (2)	0.059 (2)	0.149 (3)	−0.0130 (16)	0.044 (2)	−0.0033 (19)
C8	0.059 (2)	0.084 (3)	0.098 (3)	−0.001 (2)	0.035 (2)	0.033 (2)
C7	0.089 (3)	0.140 (4)	0.075 (2)	−0.018 (3)	0.041 (2)	0.011 (2)
C9	0.070 (3)	0.104 (4)	0.136 (5)	0.001 (3)	0.049 (3)	0.050 (3)
C10	0.062 (3)	0.065 (3)	0.171 (5)	−0.003 (2)	0.050 (3)	0.030 (3)
C11	0.094 (3)	0.076 (3)	0.276 (6)	−0.028 (3)	0.079 (3)	0.018 (3)

Geometric parameters (Å, º) top

P1—O3	1.4887 (17)	C27—H27	0.9300
P1—C24	1.779 (3)	C28—C29	1.379 (4)
P1—C12	1.786 (3)	C28—H28	0.9300
P1—C18	1.794 (3)	C29—H29	0.9300
C12—C17	1.376 (4)	O1—C1	1.301 (3)
C12—C13	1.378 (3)	O1—H1	0.7941
C13—C14	1.384 (4)	C1—O2	1.193 (3)
C13—H13	0.9300	C1—C2	1.492 (4)
C14—C15	1.356 (4)	C2—N1	1.339 (3)
C14—H14	0.9300	C2—C3	1.366 (3)
C15—C16	1.364 (4)	N1—C6	1.320 (3)
C15—H15	0.9300	C3—C4	1.385 (4)
C16—C17	1.378 (4)	C3—Cl1	1.725 (3)
C16—H16	0.9300	C4—C5	1.344 (4)
C17—H17	0.9300	C4—H4A	0.9300
C18—C23	1.364 (3)	C6—C5	1.385 (4)
C18—C19	1.371 (3)	C6—N2	1.400 (3)
C19—C20	1.385 (3)	N2—N3	1.377 (3)
C19—H19	0.9300	N2—C8	1.379 (4)
C20—C21	1.355 (4)	C5—H5A	0.9300
C20—H20	0.9300	N3—C10	1.330 (4)
C21—C22	1.351 (4)	C8—C9	1.348 (5)
C21—H21	0.9300	C8—C7	1.483 (4)
C22—C23	1.391 (4)	C7—H7A	0.9600
C22—H22	0.9300	C7—H7B	0.9600
C23—H23	0.9300	C7—H7C	0.9600
C24—C29	1.378 (3)	C9—C10	1.379 (5)
C24—C25	1.386 (3)	C9—H9	0.93 (3)
C25—C26	1.380 (3)	C10—C11	1.507 (5)
C25—H25	0.9300	C11—H11A	0.9600
C26—C27	1.358 (4)	C11—H11B	0.9600
C26—H26	0.9300	C11—H11C	0.9600
C27—C28	1.356 (4)

O3—P1—C24	112.01 (12)	C26—C27—H27	119.7
O3—P1—C12	112.87 (12)	C27—C28—C29	120.2 (3)
C24—P1—C12	106.73 (14)	C27—C28—H28	119.9
O3—P1—C18	110.91 (12)	C29—C28—H28	119.9
C24—P1—C18	106.58 (13)	C24—C29—C28	120.6 (3)
C12—P1—C18	107.40 (13)	C24—C29—H29	119.7
C17—C12—C13	118.3 (3)	C28—C29—H29	119.7
C17—C12—P1	123.1 (2)	C1—O1—H1	113.8
C13—C12—P1	118.5 (2)	O2—C1—O1	123.5 (3)
C12—C13—C14	120.3 (3)	O2—C1—C2	123.7 (3)
C12—C13—H13	119.8	O1—C1—C2	112.8 (3)
C14—C13—H13	119.8	N1—C2—C3	121.7 (3)
C15—C14—C13	120.6 (3)	N1—C2—C1	115.2 (3)
C15—C14—H14	119.7	C3—C2—C1	123.0 (3)
C13—C14—H14	119.7	C6—N1—C2	118.8 (3)
C14—C15—C16	119.7 (4)	C2—C3—C4	118.7 (3)
C14—C15—H15	120.1	C2—C3—Cl1	123.4 (3)
C16—C15—H15	120.1	C4—C3—Cl1	117.8 (3)
C15—C16—C17	120.1 (3)	C5—C4—C3	119.7 (3)
C15—C16—H16	119.9	C5—C4—H4A	120.1
C17—C16—H16	119.9	C3—C4—H4A	120.1
C12—C17—C16	120.9 (3)	N1—C6—C5	122.5 (3)
C12—C17—H17	119.5	N1—C6—N2	116.6 (3)
C16—C17—H17	119.5	C5—C6—N2	120.9 (3)
C23—C18—C19	118.8 (3)	N3—N2—C8	112.1 (3)
C23—C18—P1	117.9 (2)	N3—N2—C6	117.4 (3)
C19—C18—P1	123.3 (2)	C8—N2—C6	130.5 (3)
C18—C19—C20	120.5 (3)	C4—C5—C6	118.6 (3)
C18—C19—H19	119.7	C4—C5—H5A	120.7
C20—C19—H19	119.7	C6—C5—H5A	120.7
C21—C20—C19	119.6 (3)	C10—N3—N2	103.4 (3)
C21—C20—H20	120.2	C9—C8—N2	104.8 (4)
C19—C20—H20	120.2	C9—C8—C7	129.3 (5)
C22—C21—C20	120.9 (3)	N2—C8—C7	125.8 (3)
C22—C21—H21	119.5	C8—C7—H7A	109.5
C20—C21—H21	119.5	C8—C7—H7B	109.5
C21—C22—C23	119.4 (3)	H7A—C7—H7B	109.5
C21—C22—H22	120.3	C8—C7—H7C	109.5
C23—C22—H22	120.3	H7A—C7—H7C	109.5
C18—C23—C22	120.7 (3)	H7B—C7—H7C	109.5
C18—C23—H23	119.7	C8—C9—C10	107.9 (4)
C22—C23—H23	119.7	C8—C9—H9	126 (2)
C29—C24—C25	118.0 (3)	C10—C9—H9	126 (2)
C29—C24—P1	122.9 (2)	N3—C10—C9	111.7 (4)
C25—C24—P1	118.9 (2)	N3—C10—C11	119.0 (5)
C26—C25—C24	121.0 (3)	C9—C10—C11	129.3 (5)
C26—C25—H25	119.5	C10—C11—H11A	109.5
C24—C25—H25	119.5	C10—C11—H11B	109.5
C27—C26—C25	119.6 (3)	H11A—C11—H11B	109.5
C27—C26—H26	120.2	C10—C11—H11C	109.5
C25—C26—H26	120.2	H11A—C11—H11C	109.5
C28—C27—C26	120.7 (3)	H11B—C11—H11C	109.5
C28—C27—H27	119.7

O3—P1—C12—C17	−152.2 (2)	C26—C27—C28—C29	0.2 (5)
C24—P1—C12—C17	−28.7 (3)	C25—C24—C29—C28	0.2 (5)
C18—P1—C12—C17	85.2 (3)	P1—C24—C29—C28	175.2 (2)
O3—P1—C12—C13	29.6 (3)	C27—C28—C29—C24	−0.3 (5)
C24—P1—C12—C13	153.1 (2)	O2—C1—C2—N1	147.7 (3)
C18—P1—C12—C13	−92.9 (2)	O1—C1—C2—N1	−32.9 (3)
C17—C12—C13—C14	0.2 (4)	O2—C1—C2—C3	−33.1 (4)
P1—C12—C13—C14	178.5 (2)	O1—C1—C2—C3	146.3 (3)
C12—C13—C14—C15	0.8 (5)	C3—C2—N1—C6	1.8 (4)
C13—C14—C15—C16	−1.8 (5)	C1—C2—N1—C6	−179.0 (2)
C14—C15—C16—C17	1.7 (5)	N1—C2—C3—C4	−0.3 (4)
C13—C12—C17—C16	−0.3 (4)	C1—C2—C3—C4	−179.4 (3)
P1—C12—C17—C16	−178.5 (2)	N1—C2—C3—Cl1	177.3 (2)
C15—C16—C17—C12	−0.6 (5)	C1—C2—C3—Cl1	−1.9 (4)
O3—P1—C18—C23	19.5 (3)	C2—C3—C4—C5	−0.7 (5)
C24—P1—C18—C23	−102.6 (2)	Cl1—C3—C4—C5	−178.4 (3)
C12—P1—C18—C23	143.3 (2)	C2—N1—C6—C5	−2.4 (4)
O3—P1—C18—C19	−160.2 (2)	C2—N1—C6—N2	179.0 (2)
C24—P1—C18—C19	77.6 (3)	N1—C6—N2—N3	169.7 (2)
C12—P1—C18—C19	−36.5 (3)	C5—C6—N2—N3	−8.9 (4)
C23—C18—C19—C20	0.4 (4)	N1—C6—N2—C8	−12.4 (4)
P1—C18—C19—C20	−179.8 (2)	C5—C6—N2—C8	168.9 (3)
C18—C19—C20—C21	0.9 (5)	C3—C4—C5—C6	0.2 (5)
C19—C20—C21—C22	−1.0 (5)	N1—C6—C5—C4	1.4 (5)
C20—C21—C22—C23	−0.1 (5)	N2—C6—C5—C4	180.0 (3)
C19—C18—C23—C22	−1.6 (5)	C8—N2—N3—C10	0.8 (3)
P1—C18—C23—C22	178.7 (2)	C6—N2—N3—C10	179.1 (3)
C21—C22—C23—C18	1.4 (5)	N3—N2—C8—C9	−1.0 (4)
O3—P1—C24—C29	−104.1 (3)	C6—N2—C8—C9	−178.9 (3)
C12—P1—C24—C29	131.9 (3)	N3—N2—C8—C7	177.7 (3)
C18—P1—C24—C29	17.3 (3)	C6—N2—C8—C7	−0.2 (5)
O3—P1—C24—C25	70.8 (3)	N2—C8—C9—C10	0.8 (4)
C12—P1—C24—C25	−53.2 (3)	C7—C8—C9—C10	−177.9 (3)
C18—P1—C24—C25	−167.7 (2)	N2—N3—C10—C9	−0.3 (4)
C29—C24—C25—C26	0.0 (4)	N2—N3—C10—C11	−179.4 (3)
P1—C24—C25—C26	−175.2 (2)	C8—C9—C10—N3	−0.3 (5)
C24—C25—C26—C27	−0.1 (5)	C8—C9—C10—C11	178.7 (3)
C25—C26—C27—C28	0.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.79	1.76	2.537 (2)	165

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀ClN₃O₂·C₁₈H₁₅OP
M_r	529.94
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.6694 (14), 9.8176 (11), 18.272 (2)
β (°)	116.089 (2)
V (Å³)	2685.7 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.23 × 0.18 × 0.09

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	13279, 4721, 2333
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.083, 1.04
No. of reflections	4721
No. of parameters	337
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.27

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.79	1.76	2.537 (2)	165

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant No. 20761002). This research was sponsored by the fund of the Talent Highland research program of Guangxi University (grant No. 205121), the Science Foundation of the State Ethnic Affairs Commission (grant No. 07GX05), the Development Foundation Guangxi Research Institute of Chemical Industry, and the Science Foundation of Guangxi University for Nationalities (grant Nos. 0409032, 0409012, 0509ZD047).

References

Mann, F., Chiment, F., Balasco, A., Cenicola, M. L., Amico, M. D., Parrilo, C., Rossi, F. & Marmo, E. (1992). Eur. J. Med. Chem. 27, 633–639. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 8| August 2008| Page o1427

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-Chloro-6-(3,5-di­methyl-1H-pyrazol-1-yl)picolinic acid–tri­phenyl­phosphine oxide (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid–triphenylphosphine oxide (1/1)