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ISSN: 2056-9890

5-Benzoyl-N,4-di­phenyl-4,5-di­hydro-1H-pyrazole-3-carboxamide

aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: helongcwnu@yahoo.com.cn

(Received 28 July 2009; accepted 25 August 2009; online 29 August 2009)

The title compound, C23H19N3O2, was synthesized by the 1,3-dipolar cyclo­addition reaction of N-phenyl-α-diazo­acetamide and chalcone. In the mol­ecule, the pyrazoline ring assumes an envelope conformation. Weak inter­molecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the 1,3-dipolar cyclo­addition reaction, see: Grigg (1995[Grigg, R. (1995). Tetrahedron Asymmetry, 6, 2475-2486.]). For applications of pyrazoline and its derivatives, see: Dhal et al. (1975[Dhal, P. N., Acharya, T. E. & Nayak, A. (1975). J. Indian Chem. Soc. 52, 1196-1200.]); Lombardino & Ottemes (1981[Lombardino, G. & Ottemes, I. G. (1981). J. Med. Chem. 24, 830-834.]); Parmar et al. (1974[Parmar, S. S., Pandey, B. R., Dwivedi, C. & Harbison, R. D. (1974). J. Pharm. Sci. 63, 1152-1255.]); Rawal et al. (1963[Rawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323-326.]).

[Scheme 1]

Experimental

Crystal data
  • C23H19N3O2

  • Mr = 369.41

  • Monoclinic, P 21 /n

  • a = 5.809 (3) Å

  • b = 10.717 (5) Å

  • c = 29.428 (7) Å

  • β = 92.753 (5)°

  • V = 1829.9 (13) Å3

  • Z = 4

  • Cu Kα radiation

  • μ = 0.70 mm−1

  • T = 293 K

  • 0.36 × 0.24 × 0.20 mm

Data collection
  • Oxford Diffraction Gemini S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.786, Tmax = 0.873

  • 27720 measured reflections

  • 2929 independent reflections

  • 2390 reflections with I > 2σ(I)

  • Rint = 0.031

Refinement
  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.066

  • S = 1.00

  • 2929 reflections

  • 261 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3—H3⋯O1i 0.93 2.56 3.468 (4) 166
C8—H8⋯O1i 0.98 2.50 3.475 (4) 173
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The 1,3-dipolar cycloaddition reaction is one of the most efficient and widely used methods for the synthesis of nitrogen-containing five-membered heterocycles (Grigg, 1995). As important and useful five-membered heterocyclic compounds, pyrazoline and its derivatives were found to possess antifungal (Dhal et al., 1975), immunosuppressive (Lombardino et al.,1981), psychoanaleptic (Parmar et al. 1974), and antiviral (Rawal et al. 1963) activities. We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. In the molecule the dihydropyrazole ring assumes an envelope conformation. The C6-benene ring and C15-benene ring make dihedral angles of 82.08 (7)° and 84.78 (7)° with respect to the C23-benene ring. The dihedral angle between the C6-benzene and C15-benene ring is 71.39 (7)°. Intermolecular weak C—H···O hydrogen bonding is present in the crystal structure (Table 1).

Related literature top

For the 1,3-dipolar cycloaddition reaction, see: Grigg et al. (1995). For applications of pyrazoline and its derivatives, see: Dhal et al. (1975); Lombardino et al. (1981); Parmar et al. (1974); Rawal et al. (1963).

Experimental top

N-Phenyl-alfa-diazoacetamide (0.035 g, 0.2 mmol) and chalcone (0.042 g, 0.2 mmol) and 1,4-diaza-bicyclo[2.2.2]octan (0.02 g, 0.2 mmol) were dissolved in toluene (2 mL). The solution was warmed to 323 K, and the solution was stirred for 2 h. After removal of solvent under reduced pressure, the residue was purified through column chromatography on silica gel to give target compound. Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from ethanol.

Refinement top

Imino H atoms were located in a difference Fourier map and were refined isotropically. Other H atoms were placed in calculated positions with C—H = 0.93 or 0.98 Å, and refined using a riding model, with Uiso(H) =1.2Ueq(C).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).
5-Benzoyl-N,4-diphenyl-4,5-dihydro-1H-pyrazole-3-carboxamide top
Crystal data top
C23H19N3O2F(000) = 776
Mr = 369.41Dx = 1.341 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ynCell parameters from 11458 reflections
a = 5.809 (3) Åθ = 3.0–62.7°
b = 10.717 (5) ŵ = 0.70 mm1
c = 29.428 (7) ÅT = 293 K
β = 92.753 (5)°Block, colorless
V = 1829.9 (13) Å30.36 × 0.24 × 0.20 mm
Z = 4
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer
2929 independent reflections
Radiation source: Ultra (Cu) X-ray Source2390 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.031
Detector resolution: 15.9149 pixels mm-1θmax = 62.7°, θmin = 3.0°
ω scansh = 66
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
k = 1212
Tmin = 0.786, Tmax = 0.873l = 3333
27720 measured reflections
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0012P)2 + 1.114P]
where P = (Fo2 + 2Fc2)/3
2929 reflections(Δ/σ)max = 0.001
261 parametersΔρmax = 0.16 e Å3
2 restraintsΔρmin = 0.15 e Å3
Crystal data top
C23H19N3O2V = 1829.9 (13) Å3
Mr = 369.41Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.809 (3) ŵ = 0.70 mm1
b = 10.717 (5) ÅT = 293 K
c = 29.428 (7) Å0.36 × 0.24 × 0.20 mm
β = 92.753 (5)°
Data collection top
Oxford Diffraction Gemini S Ultra
diffractometer
2929 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2007)
2390 reflections with I > 2σ(I)
Tmin = 0.786, Tmax = 0.873Rint = 0.031
27720 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0342 restraints
wR(F2) = 0.066H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å3
2929 reflectionsΔρmin = 0.15 e Å3
261 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 > 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
xyzUiso*/Ueq
O20.5592 (2)0.44501 (12)0.90247 (4)0.0526 (3)
N10.9367 (3)0.50816 (14)0.90580 (5)0.0445 (4)
N21.0040 (2)0.35676 (13)0.83258 (4)0.0414 (3)
O10.7319 (2)0.41770 (11)0.74559 (4)0.0547 (3)
C40.4434 (3)0.27270 (15)0.72408 (5)0.0351 (4)
C180.9446 (3)0.59203 (15)0.94313 (5)0.0397 (4)
N31.0026 (2)0.26477 (14)0.79899 (5)0.0425 (4)
C90.6458 (3)0.25420 (14)0.83326 (5)0.0325 (3)
H90.49060.28850.82770.039*
C100.6433 (3)0.14494 (14)0.86613 (5)0.0336 (4)
C80.7622 (3)0.22873 (15)0.78770 (5)0.0350 (4)
H80.75010.14070.77890.042*
C170.7560 (3)0.43921 (15)0.88959 (5)0.0388 (4)
C30.3815 (3)0.14837 (16)0.71876 (6)0.0474 (4)
H30.47050.08630.73300.057*
C160.8112 (3)0.35355 (14)0.85194 (5)0.0357 (4)
C70.6522 (3)0.31416 (15)0.75101 (5)0.0370 (4)
C150.8272 (3)0.06224 (16)0.87032 (6)0.0436 (4)
H150.95050.07060.85150.052*
C230.7730 (3)0.59886 (16)0.97404 (6)0.0461 (4)
H230.64040.55080.96990.055*
C140.8282 (3)0.03262 (17)0.90231 (7)0.0540 (5)
H140.95140.08800.90470.065*
C201.1647 (4)0.74369 (18)0.98647 (6)0.0554 (5)
H201.29640.79250.99060.067*
C210.9955 (4)0.75011 (18)1.01741 (6)0.0540 (5)
H211.01250.80291.04240.065*
C60.1133 (3)0.3315 (2)0.67649 (6)0.0572 (5)
H60.02280.39320.66240.069*
C110.4622 (3)0.13108 (16)0.89459 (6)0.0447 (4)
H110.33770.18560.89210.054*
C50.3068 (3)0.36379 (17)0.70260 (6)0.0471 (4)
H50.34670.44740.70590.056*
C191.1410 (3)0.66527 (17)0.94917 (6)0.0493 (5)
H191.25600.66160.92830.059*
C220.8001 (3)0.67782 (18)1.01115 (6)0.0524 (5)
H220.68540.68211.03210.063*
C20.1871 (3)0.11665 (19)0.69215 (7)0.0597 (5)
H20.14680.03320.68840.072*
C130.6475 (4)0.04517 (19)0.93055 (7)0.0585 (5)
H130.64890.10860.95210.070*
C10.0535 (3)0.2077 (2)0.67127 (7)0.0588 (5)
H10.07730.18580.65360.071*
C120.4647 (4)0.03661 (19)0.92674 (6)0.0569 (5)
H120.34260.02840.94580.068*
H41.072 (2)0.4961 (18)0.8932 (6)0.055 (6)*
H181.081 (3)0.2914 (16)0.7754 (5)0.052 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0470 (8)0.0564 (8)0.0546 (8)0.0019 (6)0.0049 (6)0.0169 (6)
N10.0482 (10)0.0448 (9)0.0408 (8)0.0093 (7)0.0058 (7)0.0109 (7)
N20.0417 (9)0.0438 (8)0.0385 (8)0.0059 (7)0.0007 (7)0.0024 (6)
O10.0634 (9)0.0401 (7)0.0600 (8)0.0133 (6)0.0054 (6)0.0091 (6)
C40.0389 (9)0.0372 (9)0.0296 (8)0.0019 (7)0.0045 (7)0.0002 (7)
C180.0509 (11)0.0331 (9)0.0345 (9)0.0008 (8)0.0038 (8)0.0024 (7)
N30.0363 (8)0.0521 (9)0.0394 (8)0.0017 (7)0.0055 (7)0.0060 (7)
C90.0314 (9)0.0322 (8)0.0340 (8)0.0003 (7)0.0005 (7)0.0013 (7)
C100.0373 (9)0.0311 (8)0.0320 (8)0.0046 (7)0.0033 (7)0.0025 (7)
C80.0362 (9)0.0339 (9)0.0347 (8)0.0004 (7)0.0007 (7)0.0035 (7)
C170.0495 (11)0.0323 (9)0.0344 (9)0.0019 (8)0.0009 (8)0.0007 (7)
C30.0482 (11)0.0372 (10)0.0557 (11)0.0059 (8)0.0086 (9)0.0029 (8)
C160.0402 (10)0.0318 (9)0.0348 (9)0.0027 (7)0.0000 (7)0.0003 (7)
C70.0424 (10)0.0350 (9)0.0340 (9)0.0003 (8)0.0068 (7)0.0022 (7)
C150.0411 (10)0.0415 (10)0.0479 (10)0.0001 (8)0.0021 (8)0.0024 (8)
C230.0501 (11)0.0460 (10)0.0420 (10)0.0053 (9)0.0005 (8)0.0055 (8)
C140.0543 (12)0.0438 (11)0.0621 (12)0.0029 (9)0.0148 (10)0.0086 (9)
C200.0600 (13)0.0489 (11)0.0562 (12)0.0122 (10)0.0095 (10)0.0089 (9)
C210.0704 (14)0.0464 (11)0.0441 (10)0.0033 (10)0.0085 (10)0.0125 (9)
C60.0568 (13)0.0617 (13)0.0520 (12)0.0123 (10)0.0089 (10)0.0111 (10)
C110.0454 (11)0.0433 (10)0.0456 (10)0.0008 (8)0.0049 (8)0.0025 (8)
C50.0542 (12)0.0412 (10)0.0457 (10)0.0020 (9)0.0014 (9)0.0092 (8)
C190.0525 (12)0.0487 (11)0.0467 (10)0.0082 (9)0.0028 (9)0.0064 (9)
C220.0597 (13)0.0557 (12)0.0419 (10)0.0039 (10)0.0030 (9)0.0082 (9)
C20.0556 (13)0.0461 (11)0.0758 (14)0.0002 (10)0.0145 (11)0.0150 (10)
C130.0739 (15)0.0499 (12)0.0503 (11)0.0119 (11)0.0105 (10)0.0170 (9)
C10.0491 (12)0.0708 (14)0.0549 (12)0.0069 (10)0.0138 (9)0.0100 (10)
C120.0642 (14)0.0582 (12)0.0490 (11)0.0101 (11)0.0111 (10)0.0104 (10)
Geometric parameters (Å, º) top
O2—C171.223 (2)C15—C141.385 (2)
N1—C171.352 (2)C15—H150.9300
N1—C181.418 (2)C23—C221.385 (2)
N1—H40.895 (9)C23—H230.9300
N2—C161.281 (2)C14—C131.376 (3)
N2—N31.3959 (19)C14—H140.9300
O1—C71.216 (2)C20—C211.373 (3)
C4—C31.387 (2)C20—C191.384 (2)
C4—C51.391 (2)C20—H200.9300
C4—C71.485 (2)C21—C221.379 (3)
C18—C231.383 (2)C21—H210.9300
C18—C191.390 (2)C6—C51.375 (3)
N3—C81.471 (2)C6—C11.379 (3)
N3—H180.896 (9)C6—H60.9300
C9—C101.519 (2)C11—C121.385 (2)
C9—C161.519 (2)C11—H110.9300
C9—C81.555 (2)C5—H50.9300
C9—H90.9800C19—H190.9300
C10—C111.384 (2)C22—H220.9300
C10—C151.389 (2)C2—C11.373 (3)
C8—C71.532 (2)C2—H20.9300
C8—H80.9800C13—C121.377 (3)
C17—C161.486 (2)C13—H130.9300
C3—C21.385 (3)C1—H10.9300
C3—H30.9300C12—H120.9300
C17—N1—C18127.97 (16)C14—C15—H15119.8
C17—N1—H4117.2 (12)C10—C15—H15119.8
C18—N1—H4114.6 (13)C18—C23—C22119.52 (18)
C16—N2—N3108.71 (13)C18—C23—H23120.2
C3—C4—C5118.93 (16)C22—C23—H23120.2
C3—C4—C7123.26 (15)C13—C14—C15120.24 (18)
C5—C4—C7117.80 (15)C13—C14—H14119.9
C23—C18—C19119.96 (16)C15—C14—H14119.9
C23—C18—N1123.06 (16)C21—C20—C19120.62 (19)
C19—C18—N1116.91 (16)C21—C20—H20119.7
N2—N3—C8108.57 (13)C19—C20—H20119.7
N2—N3—H18109.8 (12)C20—C21—C22119.59 (18)
C8—N3—H18114.9 (12)C20—C21—H21120.2
C10—C9—C16109.58 (13)C22—C21—H21120.2
C10—C9—C8115.57 (13)C5—C6—C1119.95 (18)
C16—C9—C898.12 (12)C5—C6—H6120.0
C10—C9—H9111.0C1—C6—H6120.0
C16—C9—H9111.0C10—C11—C12120.56 (18)
C8—C9—H9111.0C10—C11—H11119.7
C11—C10—C15118.77 (16)C12—C11—H11119.7
C11—C10—C9119.93 (15)C6—C5—C4120.72 (18)
C15—C10—C9121.17 (15)C6—C5—H5119.6
N3—C8—C7111.19 (13)C4—C5—H5119.6
N3—C8—C9101.93 (12)C20—C19—C18119.61 (18)
C7—C8—C9108.60 (13)C20—C19—H19120.2
N3—C8—H8111.6C18—C19—H19120.2
C7—C8—H8111.6C21—C22—C23120.70 (19)
C9—C8—H8111.6C21—C22—H22119.6
O2—C17—N1125.75 (16)C23—C22—H22119.6
O2—C17—C16120.06 (15)C1—C2—C3120.43 (19)
N1—C17—C16114.16 (16)C1—C2—H2119.8
C2—C3—C4119.96 (17)C3—C2—H2119.8
C2—C3—H3120.0C14—C13—C12119.73 (18)
C4—C3—H3120.0C14—C13—H13120.1
N2—C16—C17122.66 (15)C12—C13—H13120.1
N2—C16—C9114.14 (14)C2—C1—C6120.00 (19)
C17—C16—C9123.20 (15)C2—C1—H1120.0
O1—C7—C4120.64 (15)C6—C1—H1120.0
O1—C7—C8119.30 (15)C13—C12—C11120.24 (19)
C4—C7—C8119.99 (14)C13—C12—H12119.9
C14—C15—C10120.45 (18)C11—C12—H12119.9
C17—N1—C18—C2311.9 (3)C3—C4—C7—C822.0 (2)
C17—N1—C18—C19171.13 (17)C5—C4—C7—C8159.26 (15)
C16—N2—N3—C818.98 (18)N3—C8—C7—O122.7 (2)
C16—C9—C10—C11102.37 (17)C9—C8—C7—O188.68 (18)
C8—C9—C10—C11147.97 (15)N3—C8—C7—C4160.37 (13)
C16—C9—C10—C1573.52 (19)C9—C8—C7—C488.26 (17)
C8—C9—C10—C1536.1 (2)C11—C10—C15—C140.3 (2)
N2—N3—C8—C786.75 (16)C9—C10—C15—C14176.24 (15)
N2—N3—C8—C928.81 (16)C19—C18—C23—C220.8 (3)
C10—C9—C8—N390.48 (15)N1—C18—C23—C22176.05 (17)
C16—C9—C8—N325.84 (14)C10—C15—C14—C130.6 (3)
C10—C9—C8—C7152.07 (13)C19—C20—C21—C220.1 (3)
C16—C9—C8—C791.60 (14)C15—C10—C11—C120.2 (3)
C18—N1—C17—O26.2 (3)C9—C10—C11—C12175.83 (16)
C18—N1—C17—C16175.71 (16)C1—C6—C5—C40.2 (3)
C5—C4—C3—C20.4 (3)C3—C4—C5—C60.0 (3)
C7—C4—C3—C2178.35 (17)C7—C4—C5—C6178.84 (16)
N3—N2—C16—C17179.69 (14)C21—C20—C19—C180.3 (3)
N3—N2—C16—C90.10 (19)C23—C18—C19—C200.7 (3)
O2—C17—C16—N2169.36 (16)N1—C18—C19—C20176.31 (17)
N1—C17—C16—N28.8 (2)C20—C21—C22—C230.0 (3)
O2—C17—C16—C911.1 (2)C18—C23—C22—C210.4 (3)
N1—C17—C16—C9170.74 (14)C4—C3—C2—C10.6 (3)
C10—C9—C16—N2103.60 (16)C15—C14—C13—C120.4 (3)
C8—C9—C16—N217.29 (17)C3—C2—C1—C60.4 (3)
C10—C9—C16—C1775.98 (19)C5—C6—C1—C20.0 (3)
C8—C9—C16—C17163.12 (14)C14—C13—C12—C110.1 (3)
C3—C4—C7—O1161.11 (17)C10—C11—C12—C130.4 (3)
C5—C4—C7—O117.6 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.563.468 (4)166
C8—H8···O1i0.982.503.475 (4)173
Symmetry code: (i) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC23H19N3O2
Mr369.41
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)5.809 (3), 10.717 (5), 29.428 (7)
β (°) 92.753 (5)
V3)1829.9 (13)
Z4
Radiation typeCu Kα
µ (mm1)0.70
Crystal size (mm)0.36 × 0.24 × 0.20
Data collection
DiffractometerOxford Diffraction Gemini S Ultra
diffractometer
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2007)
Tmin, Tmax0.786, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections
27720, 2929, 2390
Rint0.031
(sin θ/λ)max1)0.576
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.066, 1.00
No. of reflections2929
No. of parameters261
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.563.468 (4)166
C8—H8···O1i0.982.503.475 (4)173
Symmetry code: (i) x+3/2, y1/2, z+3/2.
 

Acknowledgements

The diffraction measurements were made at the Centre for Testing and Analysis, Chengdu Branch, Chinese Academy of Sciences. We acknowledge financial support from China West Normal University.

References

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First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationGrigg, R. (1995). Tetrahedron Asymmetry, 6, 2475–2486.  CrossRef CAS Web of Science Google Scholar
First citationLombardino, G. & Ottemes, I. G. (1981). J. Med. Chem. 24, 830–834.  CrossRef CAS PubMed Web of Science Google Scholar
First citationOxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
First citationParmar, S. S., Pandey, B. R., Dwivedi, C. & Harbison, R. D. (1974). J. Pharm. Sci. 63, 1152–1255.  CrossRef CAS PubMed Web of Science Google Scholar
First citationRawal, A. A., Thakor, V. M. & Shah, N. M. (1963). J. Indian Chem. Soc. 40, 323–326.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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