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

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ISSN: 2056-9890

2-[3-(4-Methoxyphen­yl)-1-phenyl-1H-pyrazol-5-yl]phenol

aAllama Iqbal Open University, Islamabad, Pakistan, bDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and cInstitut für Anorganische Chemie, J. W. Goethe-Universität, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
*Correspondence e-mail: h.aurangzeb@yahoo.com

(Received 28 January 2009; accepted 3 February 2009; online 25 February 2009)

The title compound, C22H18N2O2, was derived from 1-(2-hydroxy­phen­yl)-3-(4-methoxy­phen­yl)propane-1,3-dione. The central pyrazole ring forms dihedral angles of 16.83 (5), 48.97 (4) and 51.68 (4)°, respectively, with the methoxy­phenyl, phenyl and hydroxy­phenyl rings. The crystal packing is stabilized by O—H⋯N hydrogen bonding.

Related literature

For general synthesis, see: Ahmad et al. (1997[Ahmad, R., Zia-ul-Haq, M., Duddeck, H., Stefaniak, L. & Sitkowski, J. S. (1997). Monatsh. Chem. 128, 633-640.]). For synthetic applications, see: Beeam et al. (1984[Beeam, C. F., Hall, H. L., Huff, A. M., Tummons, R. C. & Grady, S. A. O. (1984). J. Heteroat. Chem. 21, 1897-1902.]); Bonati (1980[Bonati, F. (1980). Chim. Ind. (Roma), 62, 323-328.]); Elguero (1983[Elguero, J. (1983). Comprehensive Heterocyclic Chemistry, Vol. 5, Part 4A, pp. 167, 304. Elmford, New York: Pergamon Press.]); Freyer & Radeglia (1981[Freyer, W. & Radeglia, R. (1981). Monatsh. Chem. 112, 105-117.]); Trofinenko (1972[Trofinenko, S. (1972). Chem. Rev. 72, 497-500.]).

[Scheme 1]

Experimental

Crystal data
  • C22H18N2O2

  • Mr = 342.38

  • Monoclinic, P 21 /c

  • a = 9.5880 (5) Å

  • b = 13.7397 (8) Å

  • c = 14.2771 (7) Å

  • β = 109.340 (4)°

  • V = 1774.68 (16) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 173 (2) K

  • 0.33 × 0.31 × 0.26 mm

Data collection
  • Stoe IPDS-II two-circle diffractometer

  • Absorption correction: none

  • 24784 measured reflections

  • 4085 independent reflections

  • 3676 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.096

  • S = 1.02

  • 4085 reflections

  • 241 parameters

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

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2⋯N2i 0.91 (2) 1.88 (2) 2.7894 (11) 175.0 (17)
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; 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: XP in SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Pyrazoles are important because of their potential for biological activity. They have antipruritic, anti-inflammatory and antirheumatic effects (Beeam et al., 1984). Both traditional and new scientific methods have been used to prepare new materials for medicine (Elguero et al., 1983) and agriculture (Trofinenko, 1972). Neutral and anionic pyrazoles are excellent ligands and their coordination chemistry has been extensively studied (Bonati, 1980). Pyrazoles are also used as analytical reagents (Freyer & Radeglia, 1981). In the molecular structure of the title compound, C22H18N2O2, (Scheme 1, Fig. 1) the central pyrazole ring forms dihedral angles of 16.83 (5)°, 48.97 (4)° and 51.68 (4)° with the methoxyphenyl, phenyl and hydroxyphenyl rings, respectively. The crystal packing is stabilized by an O-H···N hydrogen bond (Table 1).

Related literature top

For general synthesis, see: Ahmad et al. (1997). For synthetic applications, see: Beeam et al. (1984); Bonati (1980); Elguero (1983); Freyer & Radeglia (1981); Trofinenko (1972).

Experimental top

1-(2'-Hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione was prepared by a modified Baker Venkataram rearrangement as reported earlier (Ahmad et al. 1997). 2-(3-(4-methxyphenyl)-1-Phenyl-1H-pyrazol-5-yl)phenol was prepared by refluxing 1-(2'-hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione (2.7 g, 10 mmol) with phenyl hydrazine (1.08 g,0.99 ml, 10 mmol) in a mixture of 50 ml absolute ethanol and 15 ml glacial acetic acid for seven hours as shown in scheme 2.The oily mixture obtained was purified by a dry silica gel column. The product was recrystallized using absolute ethanol. (Yield: 45%, m.p: 449k)

Refinement top

All H atoms could be located by difference Fourier synthesis. They were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C) or U(H) = 1.5 Ueq(Cmethyl)] using a riding model with C—H(aromatic) = 0.95Å or CH(methyl) = 0.98 Å, respectively. The hydroxyl H atom was freely refined.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the title compound.
[Figure 3] Fig. 3. The formation of the title compound.
2-[3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl]phenol top
Crystal data top
C22H18N2O2F(000) = 720
Mr = 342.38Dx = 1.281 Mg m3
Monoclinic, P21/cMelting point: 449 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 9.5880 (5) ÅCell parameters from 22780 reflections
b = 13.7397 (8) Åθ = 3.8–27.6°
c = 14.2771 (7) ŵ = 0.08 mm1
β = 109.340 (4)°T = 173 K
V = 1774.68 (16) Å3Block, colourless
Z = 40.33 × 0.31 × 0.26 mm
Data collection top
Stoe IPDS-II two-circle
diffractometer
3676 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Graphite monochromatorθmax = 27.7°, θmin = 3.7°
ω scansh = 1212
24784 measured reflectionsk = 1717
4085 independent reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0463P)2 + 0.5301P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4085 reflectionsΔρmax = 0.28 e Å3
241 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.030 (2)
Crystal data top
C22H18N2O2V = 1774.68 (16) Å3
Mr = 342.38Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.5880 (5) ŵ = 0.08 mm1
b = 13.7397 (8) ÅT = 173 K
c = 14.2771 (7) Å0.33 × 0.31 × 0.26 mm
β = 109.340 (4)°
Data collection top
Stoe IPDS-II two-circle
diffractometer
3676 reflections with I > 2σ(I)
24784 measured reflectionsRint = 0.051
4085 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.28 e Å3
4085 reflectionsΔρmin = 0.21 e Å3
241 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16266 (8)0.90595 (6)0.46141 (6)0.0317 (2)
O20.53923 (9)0.76222 (6)0.18033 (6)0.02732 (18)
H20.513 (2)0.7794 (13)0.1149 (15)0.058 (5)*
N10.54331 (9)0.65343 (6)0.43688 (6)0.02103 (18)
N20.44634 (9)0.69329 (6)0.47836 (6)0.02183 (18)
C30.33084 (11)0.72394 (7)0.40111 (7)0.0216 (2)
C40.35458 (11)0.70369 (7)0.31053 (8)0.0233 (2)
H40.29010.71850.24560.028*
C50.49012 (11)0.65812 (7)0.33524 (7)0.0209 (2)
C110.68123 (11)0.61521 (7)0.50071 (7)0.0208 (2)
C120.68218 (12)0.55147 (8)0.57656 (8)0.0256 (2)
H120.59240.53410.58680.031*
C130.81636 (13)0.51336 (9)0.63747 (9)0.0335 (3)
H130.81820.46970.68950.040*
C140.94712 (13)0.53896 (10)0.62233 (10)0.0402 (3)
H141.03820.51230.66350.048*
C150.94514 (13)0.60346 (11)0.54719 (11)0.0408 (3)
H151.03510.62130.53760.049*
C160.81212 (12)0.64223 (9)0.48577 (9)0.0302 (2)
H160.81080.68650.43440.036*
C310.20092 (11)0.77139 (7)0.41556 (8)0.0221 (2)
C320.06812 (12)0.77997 (8)0.33677 (8)0.0268 (2)
H320.06210.75440.27370.032*
C330.05622 (12)0.82502 (8)0.34791 (8)0.0268 (2)
H330.14520.83010.29310.032*
C340.04804 (11)0.86244 (8)0.44031 (8)0.0241 (2)
C350.08451 (12)0.85507 (9)0.51998 (8)0.0295 (2)
H350.09050.88080.58290.035*
C360.20682 (12)0.81060 (9)0.50782 (8)0.0282 (2)
H360.29600.80650.56250.034*
C370.29807 (12)0.92114 (10)0.38164 (9)0.0363 (3)
H37A0.27860.95930.32930.054*
H37B0.36770.95650.40630.054*
H37C0.34060.85810.35470.054*
C510.56695 (10)0.61401 (7)0.27101 (7)0.0205 (2)
C520.58662 (11)0.66787 (7)0.19256 (7)0.0216 (2)
C530.65634 (12)0.62480 (9)0.13073 (8)0.0287 (2)
H530.67250.66180.07910.034*
C540.70182 (12)0.52839 (9)0.14464 (8)0.0306 (2)
H540.74800.49950.10200.037*
C550.68004 (12)0.47382 (8)0.22094 (8)0.0279 (2)
H550.70970.40750.22970.033*
C560.61481 (11)0.51682 (8)0.28402 (8)0.0244 (2)
H560.60230.47990.33690.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0251 (4)0.0429 (5)0.0281 (4)0.0094 (3)0.0101 (3)0.0034 (3)
O20.0397 (4)0.0253 (4)0.0199 (4)0.0030 (3)0.0138 (3)0.0021 (3)
N10.0234 (4)0.0236 (4)0.0191 (4)0.0017 (3)0.0110 (3)0.0009 (3)
N20.0247 (4)0.0239 (4)0.0207 (4)0.0018 (3)0.0126 (3)0.0017 (3)
C30.0256 (5)0.0209 (5)0.0209 (5)0.0004 (4)0.0111 (4)0.0002 (4)
C40.0274 (5)0.0248 (5)0.0199 (5)0.0028 (4)0.0110 (4)0.0016 (4)
C50.0262 (5)0.0203 (4)0.0190 (5)0.0006 (4)0.0112 (4)0.0004 (4)
C110.0216 (5)0.0211 (4)0.0203 (5)0.0012 (4)0.0079 (4)0.0038 (4)
C120.0268 (5)0.0274 (5)0.0228 (5)0.0031 (4)0.0086 (4)0.0004 (4)
C130.0376 (6)0.0311 (6)0.0267 (5)0.0028 (5)0.0039 (5)0.0009 (5)
C140.0266 (6)0.0460 (7)0.0402 (7)0.0074 (5)0.0007 (5)0.0048 (6)
C150.0217 (5)0.0527 (8)0.0487 (7)0.0039 (5)0.0127 (5)0.0075 (6)
C160.0283 (5)0.0327 (6)0.0332 (6)0.0063 (4)0.0148 (4)0.0012 (5)
C310.0255 (5)0.0217 (5)0.0222 (5)0.0015 (4)0.0119 (4)0.0007 (4)
C320.0296 (5)0.0321 (6)0.0208 (5)0.0031 (4)0.0110 (4)0.0012 (4)
C330.0251 (5)0.0328 (6)0.0223 (5)0.0035 (4)0.0077 (4)0.0019 (4)
C340.0235 (5)0.0246 (5)0.0269 (5)0.0029 (4)0.0119 (4)0.0007 (4)
C350.0282 (5)0.0378 (6)0.0231 (5)0.0043 (4)0.0095 (4)0.0070 (4)
C360.0258 (5)0.0362 (6)0.0224 (5)0.0047 (4)0.0075 (4)0.0037 (4)
C370.0255 (5)0.0483 (7)0.0336 (6)0.0103 (5)0.0078 (5)0.0015 (5)
C510.0206 (4)0.0241 (5)0.0183 (4)0.0010 (4)0.0086 (4)0.0025 (4)
C520.0223 (4)0.0254 (5)0.0175 (4)0.0009 (4)0.0071 (4)0.0019 (4)
C530.0318 (5)0.0375 (6)0.0212 (5)0.0030 (5)0.0144 (4)0.0007 (4)
C540.0303 (5)0.0399 (6)0.0253 (5)0.0061 (5)0.0143 (4)0.0055 (5)
C550.0274 (5)0.0271 (5)0.0304 (5)0.0039 (4)0.0113 (4)0.0045 (4)
C560.0258 (5)0.0247 (5)0.0249 (5)0.0001 (4)0.0115 (4)0.0003 (4)
Geometric parameters (Å, º) top
O1—C341.3694 (12)C31—C321.3971 (15)
O1—C371.4307 (14)C31—C361.4067 (14)
O2—C521.3657 (13)C32—C331.3984 (15)
O2—H20.91 (2)C32—H320.9500
N1—C51.3711 (12)C33—C341.3937 (15)
N1—N21.3711 (11)C33—H330.9500
N1—C111.4341 (13)C34—C351.4006 (15)
N2—C31.3457 (13)C35—C361.3833 (15)
C3—C41.4131 (14)C35—H350.9500
C3—C311.4798 (14)C36—H360.9500
C4—C51.3790 (14)C37—H37A0.9800
C4—H40.9500C37—H37B0.9800
C5—C511.4827 (13)C37—H37C0.9800
C11—C121.3904 (14)C51—C561.4041 (14)
C11—C161.3912 (14)C51—C521.4063 (14)
C12—C131.3945 (15)C52—C531.4025 (14)
C12—H120.9500C53—C541.3881 (17)
C13—C141.3863 (18)C53—H530.9500
C13—H130.9500C54—C551.3940 (16)
C14—C151.387 (2)C54—H540.9500
C14—H140.9500C55—C561.3873 (14)
C15—C161.3924 (17)C55—H550.9500
C15—H150.9500C56—H560.9500
C16—H160.9500
C34—O1—C37118.12 (9)C33—C32—H32119.0
C52—O2—H2110.0 (12)C34—C33—C32119.22 (10)
C5—N1—N2111.75 (8)C34—C33—H33120.4
C5—N1—C11129.15 (8)C32—C33—H33120.4
N2—N1—C11119.09 (8)O1—C34—C33124.86 (10)
C3—N2—N1105.23 (8)O1—C34—C35115.55 (9)
N2—C3—C4110.50 (9)C33—C34—C35119.57 (9)
N2—C3—C31121.73 (9)C36—C35—C34120.59 (10)
C4—C3—C31127.77 (9)C36—C35—H35119.7
C5—C4—C3106.20 (9)C34—C35—H35119.7
C5—C4—H4126.9C35—C36—C31120.92 (10)
C3—C4—H4126.9C35—C36—H36119.5
N1—C5—C4106.31 (8)C31—C36—H36119.5
N1—C5—C51123.26 (9)O1—C37—H37A109.5
C4—C5—C51130.28 (9)O1—C37—H37B109.5
C12—C11—C16120.92 (10)H37A—C37—H37B109.5
C12—C11—N1119.50 (9)O1—C37—H37C109.5
C16—C11—N1119.58 (9)H37A—C37—H37C109.5
C11—C12—C13119.27 (10)H37B—C37—H37C109.5
C11—C12—H12120.4C56—C51—C52118.79 (9)
C13—C12—H12120.4C56—C51—C5120.96 (9)
C14—C13—C12120.18 (11)C52—C51—C5120.18 (9)
C14—C13—H13119.9O2—C52—C53121.86 (9)
C12—C13—H13119.9O2—C52—C51118.34 (9)
C13—C14—C15120.09 (11)C53—C52—C51119.79 (10)
C13—C14—H14120.0C54—C53—C52120.35 (10)
C15—C14—H14120.0C54—C53—H53119.8
C14—C15—C16120.45 (11)C52—C53—H53119.8
C14—C15—H15119.8C53—C54—C55120.25 (10)
C16—C15—H15119.8C53—C54—H54119.9
C11—C16—C15119.08 (11)C55—C54—H54119.9
C11—C16—H16120.5C56—C55—C54119.64 (10)
C15—C16—H16120.5C56—C55—H55120.2
C32—C31—C36117.71 (9)C54—C55—H55120.2
C32—C31—C3120.64 (9)C55—C56—C51121.13 (10)
C36—C31—C3121.64 (9)C55—C56—H56119.4
C31—C32—C33121.98 (10)C51—C56—H56119.4
C31—C32—H32119.0
C5—N1—N2—C30.35 (11)C36—C31—C32—C330.50 (16)
C11—N1—N2—C3178.79 (8)C3—C31—C32—C33179.54 (10)
N1—N2—C3—C40.10 (11)C31—C32—C33—C340.12 (17)
N1—N2—C3—C31179.72 (9)C37—O1—C34—C334.99 (16)
N2—C3—C4—C50.51 (12)C37—O1—C34—C35176.10 (11)
C31—C3—C4—C5179.30 (10)C32—C33—C34—O1178.32 (10)
N2—N1—C5—C40.67 (11)C32—C33—C34—C350.54 (17)
C11—N1—C5—C4178.37 (9)O1—C34—C35—C36178.63 (11)
N2—N1—C5—C51175.35 (9)C33—C34—C35—C360.33 (17)
C11—N1—C5—C515.61 (16)C34—C35—C36—C310.31 (18)
C3—C4—C5—N10.69 (11)C32—C31—C36—C350.72 (17)
C3—C4—C5—C51174.95 (10)C3—C31—C36—C35179.74 (10)
C5—N1—C11—C12131.50 (11)N1—C5—C51—C5650.34 (14)
N2—N1—C11—C1249.52 (13)C4—C5—C51—C56124.66 (12)
C5—N1—C11—C1648.36 (15)N1—C5—C51—C52132.78 (10)
N2—N1—C11—C16130.62 (10)C4—C5—C51—C5252.22 (15)
C16—C11—C12—C130.83 (16)C56—C51—C52—O2179.78 (9)
N1—C11—C12—C13179.03 (9)C5—C51—C52—O22.83 (14)
C11—C12—C13—C140.03 (17)C56—C51—C52—C531.56 (15)
C12—C13—C14—C150.71 (19)C5—C51—C52—C53178.50 (9)
C13—C14—C15—C160.7 (2)O2—C52—C53—C54179.36 (10)
C12—C11—C16—C150.87 (17)C51—C52—C53—C542.03 (16)
N1—C11—C16—C15178.98 (10)C52—C53—C54—C550.71 (17)
C14—C15—C16—C110.13 (19)C53—C54—C55—C561.06 (17)
N2—C3—C31—C32163.44 (10)C54—C55—C56—C511.52 (16)
C4—C3—C31—C3216.36 (16)C52—C51—C56—C550.20 (15)
N2—C3—C31—C3617.57 (15)C5—C51—C56—C55176.71 (10)
C4—C3—C31—C36162.64 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N2i0.91 (2)1.88 (2)2.7894 (11)175.0 (17)
Symmetry code: (i) x, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formulaC22H18N2O2
Mr342.38
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)9.5880 (5), 13.7397 (8), 14.2771 (7)
β (°) 109.340 (4)
V3)1774.68 (16)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.33 × 0.31 × 0.26
Data collection
DiffractometerStoe IPDS-II two-circle
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
24784, 4085, 3676
Rint0.051
(sin θ/λ)max1)0.653
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.096, 1.02
No. of reflections4085
No. of parameters241
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.21

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N2i0.91 (2)1.88 (2)2.7894 (11)175.0 (17)
Symmetry code: (i) x, y+3/2, z1/2.
 

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for the grant that supported this work.

References

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