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

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ISSN: 2056-9890

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

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[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.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10ClN3O2·C18H15OP

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.979

  • 13279 measured reflections

  • 4721 independent reflections

  • 2333 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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%.

Refinement top

The C-bound H atoms were positoned geometrically (C—H = 0.93-0.96Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The O-bound H atom was located in a difference map and refined as riding in its as-found relative position with Uiso(H) =1.5Ueq(O).

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
[Figure 1] 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·C18H15OPF(000) = 1104
Mr = 529.94Dx = 1.311 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2022 reflections
a = 16.6694 (14) Åθ = 2.3–25.2°
b = 9.8176 (11) ŵ = 0.24 mm1
c = 18.272 (2) ÅT = 298 K
β = 116.089 (2)°Block, colourless
V = 2685.7 (5) Å30.23 × 0.18 × 0.09 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer
4721 independent reflections
Radiation source: fine-focus sealed tube2333 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.063
ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1919
Tmin = 0.947, Tmax = 0.979k = 1111
13279 measured reflectionsl = 1121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0142P)2]
where P = (Fo2 + 2Fc2)/3
4721 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C11H10ClN3O2·C18H15OPV = 2685.7 (5) Å3
Mr = 529.94Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.6694 (14) ŵ = 0.24 mm1
b = 9.8176 (11) ÅT = 298 K
c = 18.272 (2) Å0.23 × 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)
Tmin = 0.947, Tmax = 0.979Rint = 0.063
13279 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.083H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.18 e Å3
4721 reflectionsΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
P10.12197 (5)0.76008 (8)0.14024 (4)0.0528 (2)
O30.16936 (11)0.88630 (18)0.18229 (10)0.0645 (5)
C120.18622 (17)0.6094 (3)0.18123 (18)0.0533 (7)
C130.24643 (19)0.6082 (3)0.2624 (2)0.0723 (9)
H130.25380.68550.29410.087*
C140.2960 (2)0.4923 (4)0.2970 (2)0.0887 (11)
H140.33590.49200.35200.106*
C150.2869 (2)0.3793 (4)0.2513 (3)0.0828 (11)
H150.32160.30270.27450.099*
C160.2266 (2)0.3784 (3)0.1711 (2)0.0783 (10)
H160.21900.30030.14000.094*
C170.17677 (19)0.4932 (3)0.13616 (18)0.0683 (9)
H170.13620.49190.08130.082*
C180.01884 (17)0.7409 (3)0.14774 (15)0.0504 (7)
C190.0251 (2)0.6190 (3)0.13663 (17)0.0683 (9)
H190.00130.54120.12470.082*
C200.1048 (2)0.6108 (3)0.14302 (19)0.0800 (10)
H200.13390.52770.13620.096*
C210.1400 (2)0.7247 (4)0.15932 (19)0.0793 (10)
H210.19390.71930.16270.095*
C220.0977 (2)0.8459 (4)0.1707 (2)0.0884 (11)
H220.12240.92350.18180.106*
C230.0169 (2)0.8536 (3)0.16571 (18)0.0732 (9)
H230.01300.93640.17470.088*
C240.09431 (19)0.7625 (3)0.03445 (16)0.0542 (7)
C250.16220 (19)0.7500 (3)0.01058 (19)0.0682 (9)
H250.22030.73380.04960.082*
C260.1448 (2)0.7614 (3)0.0703 (2)0.0781 (9)
H260.19090.75290.08570.094*
C270.0600 (3)0.7849 (3)0.1274 (2)0.0841 (11)
H270.04820.79260.18190.101*
C280.0077 (2)0.7974 (3)0.1057 (2)0.0905 (12)
H280.06550.81330.14530.109*
C290.0090 (2)0.7866 (3)0.02499 (19)0.0721 (9)
H290.03780.79560.01060.086*
O10.29030 (12)1.0307 (2)0.28946 (12)0.0745 (6)
H10.24710.99010.25950.112*
C10.32200 (18)0.9910 (3)0.36492 (19)0.0551 (8)
O20.29977 (14)0.8882 (2)0.38566 (13)0.0925 (7)
C20.38830 (17)1.0884 (3)0.42273 (18)0.0496 (7)
N10.43821 (15)1.1548 (2)0.39350 (13)0.0558 (6)
C30.39748 (18)1.1108 (3)0.49982 (19)0.0620 (8)
Cl10.33173 (5)1.03306 (10)0.53878 (5)0.0911 (3)
C40.4605 (2)1.2043 (4)0.5487 (2)0.0834 (11)
H4A0.46741.22180.60110.100*
C60.49929 (19)1.2413 (3)0.4415 (2)0.0610 (8)
N20.55065 (16)1.3065 (3)0.4085 (2)0.0720 (8)
C50.5116 (2)1.2697 (3)0.5199 (2)0.0819 (10)
H5A0.55421.33260.55210.098*
N30.60429 (19)1.4127 (3)0.45224 (19)0.0929 (10)
C80.5594 (2)1.2799 (4)0.3382 (3)0.0800 (11)
C70.5137 (2)1.1695 (4)0.27913 (19)0.0996 (12)
H7A0.53101.17280.23550.149*
H7B0.45021.18120.25740.149*
H7C0.53021.08300.30610.149*
C90.6186 (3)1.3730 (5)0.3377 (3)0.1022 (15)
H90.638 (2)1.383 (4)0.298 (2)0.123*
C100.6447 (2)1.4513 (4)0.4071 (3)0.0998 (15)
C110.7108 (2)1.5670 (4)0.4364 (3)0.1496 (18)
H11A0.71451.60110.48710.224*
H11B0.69151.63860.39660.224*
H11C0.76851.53490.44430.224*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0495 (5)0.0512 (5)0.0563 (5)0.0002 (4)0.0221 (4)0.0042 (4)
O30.0573 (12)0.0545 (13)0.0719 (13)0.0055 (11)0.0194 (10)0.0128 (10)
C120.0508 (19)0.051 (2)0.060 (2)0.0008 (15)0.0264 (17)0.0001 (16)
C130.070 (2)0.061 (2)0.075 (2)0.0039 (19)0.023 (2)0.0053 (19)
C140.073 (3)0.078 (3)0.091 (3)0.002 (2)0.013 (2)0.023 (2)
C150.067 (2)0.067 (3)0.115 (3)0.013 (2)0.039 (2)0.026 (2)
C160.085 (3)0.059 (3)0.106 (3)0.012 (2)0.056 (2)0.001 (2)
C170.071 (2)0.061 (2)0.075 (2)0.0125 (19)0.0339 (19)0.002 (2)
C180.0521 (17)0.0464 (19)0.0552 (17)0.0014 (17)0.0259 (14)0.0045 (16)
C190.066 (2)0.060 (2)0.088 (2)0.0017 (18)0.0424 (19)0.0111 (18)
C200.071 (2)0.066 (3)0.112 (3)0.010 (2)0.049 (2)0.009 (2)
C210.063 (2)0.080 (3)0.106 (3)0.001 (2)0.048 (2)0.004 (2)
C220.079 (3)0.071 (3)0.134 (3)0.010 (2)0.064 (2)0.011 (2)
C230.070 (2)0.056 (2)0.106 (3)0.0042 (19)0.050 (2)0.007 (2)
C240.0568 (19)0.0489 (19)0.0603 (19)0.0006 (17)0.0288 (17)0.0004 (16)
C250.069 (2)0.071 (2)0.072 (2)0.0076 (19)0.0368 (18)0.0017 (19)
C260.099 (3)0.073 (2)0.083 (3)0.010 (2)0.059 (2)0.003 (2)
C270.114 (3)0.082 (3)0.063 (2)0.008 (2)0.044 (3)0.0024 (19)
C280.081 (3)0.118 (3)0.063 (3)0.008 (2)0.024 (2)0.019 (2)
C290.063 (2)0.088 (3)0.067 (2)0.0002 (19)0.0297 (19)0.0139 (18)
O10.0828 (15)0.0717 (15)0.0631 (14)0.0256 (12)0.0267 (12)0.0080 (12)
C10.053 (2)0.054 (2)0.064 (2)0.0020 (17)0.0309 (18)0.0027 (19)
O20.1069 (18)0.0782 (18)0.0849 (16)0.0368 (15)0.0353 (13)0.0044 (14)
C20.0451 (18)0.0485 (19)0.055 (2)0.0011 (15)0.0213 (16)0.0003 (15)
N10.0491 (15)0.0534 (17)0.0658 (17)0.0057 (13)0.0262 (14)0.0016 (13)
C30.055 (2)0.072 (2)0.062 (2)0.0038 (18)0.0289 (17)0.0020 (18)
Cl10.0865 (6)0.1195 (8)0.0837 (6)0.0107 (6)0.0526 (5)0.0067 (5)
C40.076 (2)0.103 (3)0.069 (2)0.014 (2)0.030 (2)0.018 (2)
C60.0494 (19)0.054 (2)0.076 (2)0.0038 (17)0.0248 (18)0.005 (2)
N20.0549 (17)0.061 (2)0.098 (2)0.0123 (14)0.0318 (17)0.0078 (17)
C50.069 (2)0.085 (3)0.085 (3)0.023 (2)0.027 (2)0.023 (2)
N30.067 (2)0.059 (2)0.149 (3)0.0130 (16)0.044 (2)0.0033 (19)
C80.059 (2)0.084 (3)0.098 (3)0.001 (2)0.035 (2)0.033 (2)
C70.089 (3)0.140 (4)0.075 (2)0.018 (3)0.041 (2)0.011 (2)
C90.070 (3)0.104 (4)0.136 (5)0.001 (3)0.049 (3)0.050 (3)
C100.062 (3)0.065 (3)0.171 (5)0.003 (2)0.050 (3)0.030 (3)
C110.094 (3)0.076 (3)0.276 (6)0.028 (3)0.079 (3)0.018 (3)
Geometric parameters (Å, º) top
P1—O31.4887 (17)C27—H270.9300
P1—C241.779 (3)C28—C291.379 (4)
P1—C121.786 (3)C28—H280.9300
P1—C181.794 (3)C29—H290.9300
C12—C171.376 (4)O1—C11.301 (3)
C12—C131.378 (3)O1—H10.7941
C13—C141.384 (4)C1—O21.193 (3)
C13—H130.9300C1—C21.492 (4)
C14—C151.356 (4)C2—N11.339 (3)
C14—H140.9300C2—C31.366 (3)
C15—C161.364 (4)N1—C61.320 (3)
C15—H150.9300C3—C41.385 (4)
C16—C171.378 (4)C3—Cl11.725 (3)
C16—H160.9300C4—C51.344 (4)
C17—H170.9300C4—H4A0.9300
C18—C231.364 (3)C6—C51.385 (4)
C18—C191.371 (3)C6—N21.400 (3)
C19—C201.385 (3)N2—N31.377 (3)
C19—H190.9300N2—C81.379 (4)
C20—C211.355 (4)C5—H5A0.9300
C20—H200.9300N3—C101.330 (4)
C21—C221.351 (4)C8—C91.348 (5)
C21—H210.9300C8—C71.483 (4)
C22—C231.391 (4)C7—H7A0.9600
C22—H220.9300C7—H7B0.9600
C23—H230.9300C7—H7C0.9600
C24—C291.378 (3)C9—C101.379 (5)
C24—C251.386 (3)C9—H90.93 (3)
C25—C261.380 (3)C10—C111.507 (5)
C25—H250.9300C11—H11A0.9600
C26—C271.358 (4)C11—H11B0.9600
C26—H260.9300C11—H11C0.9600
C27—C281.356 (4)
O3—P1—C24112.01 (12)C26—C27—H27119.7
O3—P1—C12112.87 (12)C27—C28—C29120.2 (3)
C24—P1—C12106.73 (14)C27—C28—H28119.9
O3—P1—C18110.91 (12)C29—C28—H28119.9
C24—P1—C18106.58 (13)C24—C29—C28120.6 (3)
C12—P1—C18107.40 (13)C24—C29—H29119.7
C17—C12—C13118.3 (3)C28—C29—H29119.7
C17—C12—P1123.1 (2)C1—O1—H1113.8
C13—C12—P1118.5 (2)O2—C1—O1123.5 (3)
C12—C13—C14120.3 (3)O2—C1—C2123.7 (3)
C12—C13—H13119.8O1—C1—C2112.8 (3)
C14—C13—H13119.8N1—C2—C3121.7 (3)
C15—C14—C13120.6 (3)N1—C2—C1115.2 (3)
C15—C14—H14119.7C3—C2—C1123.0 (3)
C13—C14—H14119.7C6—N1—C2118.8 (3)
C14—C15—C16119.7 (4)C2—C3—C4118.7 (3)
C14—C15—H15120.1C2—C3—Cl1123.4 (3)
C16—C15—H15120.1C4—C3—Cl1117.8 (3)
C15—C16—C17120.1 (3)C5—C4—C3119.7 (3)
C15—C16—H16119.9C5—C4—H4A120.1
C17—C16—H16119.9C3—C4—H4A120.1
C12—C17—C16120.9 (3)N1—C6—C5122.5 (3)
C12—C17—H17119.5N1—C6—N2116.6 (3)
C16—C17—H17119.5C5—C6—N2120.9 (3)
C23—C18—C19118.8 (3)N3—N2—C8112.1 (3)
C23—C18—P1117.9 (2)N3—N2—C6117.4 (3)
C19—C18—P1123.3 (2)C8—N2—C6130.5 (3)
C18—C19—C20120.5 (3)C4—C5—C6118.6 (3)
C18—C19—H19119.7C4—C5—H5A120.7
C20—C19—H19119.7C6—C5—H5A120.7
C21—C20—C19119.6 (3)C10—N3—N2103.4 (3)
C21—C20—H20120.2C9—C8—N2104.8 (4)
C19—C20—H20120.2C9—C8—C7129.3 (5)
C22—C21—C20120.9 (3)N2—C8—C7125.8 (3)
C22—C21—H21119.5C8—C7—H7A109.5
C20—C21—H21119.5C8—C7—H7B109.5
C21—C22—C23119.4 (3)H7A—C7—H7B109.5
C21—C22—H22120.3C8—C7—H7C109.5
C23—C22—H22120.3H7A—C7—H7C109.5
C18—C23—C22120.7 (3)H7B—C7—H7C109.5
C18—C23—H23119.7C8—C9—C10107.9 (4)
C22—C23—H23119.7C8—C9—H9126 (2)
C29—C24—C25118.0 (3)C10—C9—H9126 (2)
C29—C24—P1122.9 (2)N3—C10—C9111.7 (4)
C25—C24—P1118.9 (2)N3—C10—C11119.0 (5)
C26—C25—C24121.0 (3)C9—C10—C11129.3 (5)
C26—C25—H25119.5C10—C11—H11A109.5
C24—C25—H25119.5C10—C11—H11B109.5
C27—C26—C25119.6 (3)H11A—C11—H11B109.5
C27—C26—H26120.2C10—C11—H11C109.5
C25—C26—H26120.2H11A—C11—H11C109.5
C28—C27—C26120.7 (3)H11B—C11—H11C109.5
C28—C27—H27119.7
O3—P1—C12—C17152.2 (2)C26—C27—C28—C290.2 (5)
C24—P1—C12—C1728.7 (3)C25—C24—C29—C280.2 (5)
C18—P1—C12—C1785.2 (3)P1—C24—C29—C28175.2 (2)
O3—P1—C12—C1329.6 (3)C27—C28—C29—C240.3 (5)
C24—P1—C12—C13153.1 (2)O2—C1—C2—N1147.7 (3)
C18—P1—C12—C1392.9 (2)O1—C1—C2—N132.9 (3)
C17—C12—C13—C140.2 (4)O2—C1—C2—C333.1 (4)
P1—C12—C13—C14178.5 (2)O1—C1—C2—C3146.3 (3)
C12—C13—C14—C150.8 (5)C3—C2—N1—C61.8 (4)
C13—C14—C15—C161.8 (5)C1—C2—N1—C6179.0 (2)
C14—C15—C16—C171.7 (5)N1—C2—C3—C40.3 (4)
C13—C12—C17—C160.3 (4)C1—C2—C3—C4179.4 (3)
P1—C12—C17—C16178.5 (2)N1—C2—C3—Cl1177.3 (2)
C15—C16—C17—C120.6 (5)C1—C2—C3—Cl11.9 (4)
O3—P1—C18—C2319.5 (3)C2—C3—C4—C50.7 (5)
C24—P1—C18—C23102.6 (2)Cl1—C3—C4—C5178.4 (3)
C12—P1—C18—C23143.3 (2)C2—N1—C6—C52.4 (4)
O3—P1—C18—C19160.2 (2)C2—N1—C6—N2179.0 (2)
C24—P1—C18—C1977.6 (3)N1—C6—N2—N3169.7 (2)
C12—P1—C18—C1936.5 (3)C5—C6—N2—N38.9 (4)
C23—C18—C19—C200.4 (4)N1—C6—N2—C812.4 (4)
P1—C18—C19—C20179.8 (2)C5—C6—N2—C8168.9 (3)
C18—C19—C20—C210.9 (5)C3—C4—C5—C60.2 (5)
C19—C20—C21—C221.0 (5)N1—C6—C5—C41.4 (5)
C20—C21—C22—C230.1 (5)N2—C6—C5—C4180.0 (3)
C19—C18—C23—C221.6 (5)C8—N2—N3—C100.8 (3)
P1—C18—C23—C22178.7 (2)C6—N2—N3—C10179.1 (3)
C21—C22—C23—C181.4 (5)N3—N2—C8—C91.0 (4)
O3—P1—C24—C29104.1 (3)C6—N2—C8—C9178.9 (3)
C12—P1—C24—C29131.9 (3)N3—N2—C8—C7177.7 (3)
C18—P1—C24—C2917.3 (3)C6—N2—C8—C70.2 (5)
O3—P1—C24—C2570.8 (3)N2—C8—C9—C100.8 (4)
C12—P1—C24—C2553.2 (3)C7—C8—C9—C10177.9 (3)
C18—P1—C24—C25167.7 (2)N2—N3—C10—C90.3 (4)
C29—C24—C25—C260.0 (4)N2—N3—C10—C11179.4 (3)
P1—C24—C25—C26175.2 (2)C8—C9—C10—N30.3 (5)
C24—C25—C26—C270.1 (5)C8—C9—C10—C11178.7 (3)
C25—C26—C27—C280.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O30.791.762.537 (2)165

Experimental details

Crystal data
Chemical formulaC11H10ClN3O2·C18H15OP
Mr529.94
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)16.6694 (14), 9.8176 (11), 18.272 (2)
β (°) 116.089 (2)
V3)2685.7 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.23 × 0.18 × 0.09
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.947, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
13279, 4721, 2333
Rint0.063
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.083, 1.04
No. of reflections4721
No. of parameters337
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···O30.791.762.537 (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

First citationMann, 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
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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