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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o729.
Published online 2008 March 20. doi:  10.1107/S160053680800706X
PMCID: PMC2961064

Diethyl 2-[(4-nitro­phen­yl)(4-phenyl-1,2,3-selenadiazol-5-yl)meth­yl]malonate

Abstract

In the title compound, C22H21N3O6Se, the heterocyclic ring makes dihedral angles of 50.03 (11) and 67.75 (11)°, respectively, with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions: the site occupancies for the C atoms are 0.62 (3)/0.38 (3) and 0.48 (3)/0.52 (3). In the crystal structure, weak intra- and inter­molecular C—H(...)O inter­actions are observed.

Related literature

For biological activities, see: El-Kashef et al. (1986 [triangle]); El-Bahaie et al. (1990 [triangle]). For closely related compounds, see: Bertini et al. (1984 [triangle]); Gunasekaran et al. (2007 [triangle]).

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Object name is e-64-0o729-scheme1.jpg

Experimental

Crystal data

  • C22H21N3O6Se
  • M r = 502.38
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o729-efi1.jpg
  • a = 9.9530 (6) Å
  • b = 10.5220 (6) Å
  • c = 12.2305 (7) Å
  • α = 79.350 (3)°
  • β = 74.632 (3)°
  • γ = 67.632 (3)°
  • V = 1137.05 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.69 mm−1
  • T = 295 (2) K
  • 0.23 × 0.17 × 0.16 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.697, T max = 0.773
  • 30194 measured reflections
  • 4477 independent reflections
  • 3053 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.053
  • wR(F 2) = 0.161
  • S = 1.04
  • 4477 reflections
  • 313 parameters
  • 4 restraints
  • H-atom parameters constrained
  • Δρmax = 0.93 e Å−3
  • Δρmin = −0.80 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800706X/is2278sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800706X/is2278Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Selenium containing compounds like 1,2,3-selenadiazole possess various beneficial activities like antibacterial (El-Kashef et al., 1986), antimicrobial (El-Bahaie et al., 1990) activities. The geometric parameters in the compound, (I) (Fig. 1), agree with the reported values of similar structures (Bertini et al., 1984; Gunasekaran et al., 2007).

The heterocyclic ring makes the dihedral angles of 50.03 (11) and 67.75 (11)° with the benzene and phenyl rings. The terminal C atoms of the ester groups are disordered over two positions; the site occupancies for the C atoms are 0.62/0.38 and 0.48/0.52. The molecular structure is stabilized by weak intramolecular C—H···O interactions and the crystal packing of (I) is stabilized by weak intermolecular C—H···O contacts (Table 1 and Fig. 2).

Experimental

2.22 g (0.02 mol) of powdered selenium dioxide was dissolved in glacial acetic acid by gentle warming. To this warm solution, 0.002 mol of diethyl 2-{3-[2-(aminocarbonyl)hydrazono]-1-(4-nitrophenyl)-3-phenylpropyl} malonate was added at once and the mixture was gently heated on a water bath until gas evolution ceased. The selenium deposited on cooling was removed by filtration and the filtrate poured into crushed ice, extracted with chloroform and purified by column chromatography, using silica gel (60–120 mesh) to yield diethyl 2-[(4-nitrophenyl) (4-phenyl-1,2,3-selenadiazol-5-yl)methyl]malonate. Solvent used for crystallization is ethanol.

Refinement

The site occupancy factors were refined as C19 = 0.62 (3), C19A = 0.38 (3), C22 = 0.48 (3) and C22A = 0.52 (3) during anisotropic refinement. The C21—C22A, C21—C22, C18—C19 and C18—C19A bond distances were restrained to be 1.5 (1) Å. H atoms were positioned geometrically and refined using riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C) for aromatic C—H, C—H = 0.98 Å and Uiso(H) = 1.2Ueq(C) for CH, C—H = 0.97 Å and Uiso(H) = 1.2Ueq(C) for CH2, and C—H = 0.96 Å and Uiso(H) = 1.5Ueq(C) for CH3.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bonds have been omitted.

Crystal data

C22H21N3O6SeZ = 2
Mr = 502.38F000 = 512
Triclinic, P1Dx = 1.467 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 9.9530 (6) ÅCell parameters from 8446 reflections
b = 10.5220 (6) Åθ = 1.7–26º
c = 12.2305 (7) ŵ = 1.69 mm1
α = 79.350 (3)ºT = 295 (2) K
β = 74.632 (3)ºBlock, colourless
γ = 67.632 (3)º0.23 × 0.17 × 0.16 mm
V = 1137.05 (11) Å3

Data collection

Bruker SMART APEX area-detector diffractometer4477 independent reflections
Radiation source: fine-focus sealed tube3053 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 295(2) Kθmax = 26.1º
ω and [var phi] scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.697, Tmax = 0.773k = −12→12
30194 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.161  w = 1/[σ2(Fo2) + (0.0776P)2 + 0.9842P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4477 reflectionsΔρmax = 0.93 e Å3
313 parametersΔρmin = −0.80 e Å3
4 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Se11.00900 (5)0.21345 (6)0.44996 (4)0.0888 (3)
O11.5749 (5)0.1019 (4)−0.0847 (4)0.1160 (15)
O21.6666 (5)0.0959 (5)0.0564 (5)0.1327 (17)
O40.7916 (3)0.6035 (4)0.4808 (2)0.0859 (10)
O61.0425 (4)0.6499 (3)0.1149 (2)0.0859 (10)
N10.8397 (5)0.1628 (5)0.5006 (4)0.0939 (13)
N20.7447 (4)0.2286 (4)0.4410 (3)0.0753 (10)
N31.5628 (6)0.1283 (4)0.0109 (5)0.0929 (14)
C10.7808 (4)0.3215 (4)0.3527 (3)0.0558 (9)
C20.9155 (4)0.3332 (4)0.3410 (3)0.0521 (8)
C30.6670 (4)0.4007 (4)0.2854 (3)0.0542 (9)
C40.5213 (5)0.4674 (5)0.3410 (4)0.0686 (11)
H40.49520.45630.42010.082*
C50.4156 (5)0.5494 (5)0.2804 (5)0.0807 (13)
H50.31930.59530.31870.097*
C60.4514 (6)0.5637 (5)0.1641 (5)0.0837 (14)
H60.38010.61980.12310.100*
C70.5930 (6)0.4949 (5)0.1085 (4)0.0796 (13)
H70.61680.50310.02930.095*
C80.7013 (5)0.4133 (5)0.1679 (3)0.0640 (10)
H80.79700.36710.12880.077*
C90.9818 (4)0.4288 (4)0.2556 (3)0.0495 (8)
H90.91990.46610.19870.059*
C101.1371 (4)0.3504 (4)0.1923 (3)0.0509 (8)
C111.1559 (5)0.3109 (4)0.0853 (3)0.0627 (10)
H111.07390.33460.05290.075*
C121.2940 (5)0.2375 (5)0.0274 (4)0.0738 (12)
H121.30630.2109−0.04410.089*
C131.4136 (5)0.2034 (4)0.0754 (4)0.0696 (12)
C141.4005 (5)0.2414 (4)0.1802 (4)0.0677 (11)
H141.48370.21820.21100.081*
C151.2595 (4)0.3154 (4)0.2393 (3)0.0592 (9)
H151.24770.34130.31090.071*
C160.9754 (4)0.5531 (4)0.3084 (3)0.0529 (9)
H161.04740.52050.35770.064*
C170.8230 (4)0.6224 (4)0.3794 (3)0.0574 (9)
O30.7304 (3)0.7037 (3)0.3154 (3)0.0766 (8)
C180.5803 (5)0.7789 (5)0.3722 (6)0.110 (2)
H18A0.56020.74130.45100.132*0.62 (3)
H18B0.50880.77320.33450.132*0.62 (3)
H18C0.58340.79120.44810.132*0.38 (3)
H18D0.52130.72100.38110.132*0.38 (3)
C190.571 (2)0.9256 (10)0.366 (2)0.150 (8)0.62 (3)
H19A0.62970.93170.41390.226*0.62 (3)
H19B0.46900.98300.39070.226*0.62 (3)
H19C0.60740.95610.28860.226*0.62 (3)
C19A0.500 (3)0.917 (2)0.318 (2)0.140 (12)0.38 (3)
H19D0.57040.95730.27110.209*0.38 (3)
H19E0.43600.97690.37600.209*0.38 (3)
H19F0.44070.90710.27170.209*0.38 (3)
C201.0180 (4)0.6576 (4)0.2149 (3)0.0580 (10)
O51.0258 (4)0.7581 (3)0.2602 (3)0.0796 (9)
C211.0583 (9)0.8667 (6)0.1809 (6)0.131 (3)
H21A1.00110.88950.12240.157*0.48 (3)
H21B1.16290.83460.14420.157*0.48 (3)
H21C1.06770.84800.10400.157*0.52 (3)
H21D1.15210.87050.18640.157*0.52 (3)
C221.022 (4)0.9937 (15)0.2377 (14)0.109 (8)0.48 (3)
H22A0.92621.01380.28800.164*0.48 (3)
H22B1.02211.07020.18100.164*0.48 (3)
H22C1.09610.97860.28060.164*0.48 (3)
C22A0.937 (2)1.0027 (12)0.205 (2)0.152 (8)0.52 (3)
H22D0.85331.01010.17650.228*0.52 (3)
H22E0.97271.07630.16940.228*0.52 (3)
H22F0.90721.00870.28620.228*0.52 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Se10.0812 (4)0.1012 (4)0.0863 (4)−0.0446 (3)−0.0377 (3)0.0424 (3)
O10.116 (3)0.095 (3)0.110 (3)−0.042 (2)0.047 (3)−0.035 (2)
O20.067 (2)0.126 (4)0.170 (5)−0.014 (2)0.018 (3)−0.035 (3)
O40.0721 (19)0.109 (2)0.0520 (17)−0.0186 (18)0.0079 (14)−0.0072 (16)
O60.125 (3)0.082 (2)0.0519 (18)−0.051 (2)−0.0073 (17)0.0087 (14)
N10.091 (3)0.103 (3)0.085 (3)−0.051 (2)−0.023 (2)0.041 (2)
N20.070 (2)0.082 (2)0.070 (2)−0.039 (2)−0.0106 (18)0.0203 (19)
N30.076 (3)0.067 (3)0.115 (4)−0.029 (2)0.025 (3)−0.014 (3)
C10.059 (2)0.060 (2)0.049 (2)−0.0287 (18)−0.0026 (16)−0.0018 (16)
C20.056 (2)0.054 (2)0.0456 (19)−0.0232 (17)−0.0087 (16)0.0014 (15)
C30.054 (2)0.058 (2)0.055 (2)−0.0286 (18)−0.0118 (17)0.0014 (17)
C40.061 (3)0.082 (3)0.066 (3)−0.033 (2)−0.004 (2)−0.011 (2)
C50.055 (3)0.082 (3)0.109 (4)−0.022 (2)−0.021 (3)−0.018 (3)
C60.080 (3)0.076 (3)0.108 (4)−0.035 (3)−0.047 (3)0.015 (3)
C70.087 (3)0.100 (3)0.068 (3)−0.052 (3)−0.032 (2)0.017 (2)
C80.060 (2)0.080 (3)0.059 (2)−0.037 (2)−0.0125 (19)0.002 (2)
C90.0473 (19)0.054 (2)0.0480 (19)−0.0215 (16)−0.0091 (15)0.0014 (15)
C100.052 (2)0.0492 (19)0.049 (2)−0.0221 (17)−0.0031 (16)−0.0016 (15)
C110.065 (2)0.071 (3)0.053 (2)−0.030 (2)−0.0024 (19)−0.0099 (19)
C120.083 (3)0.077 (3)0.061 (2)−0.038 (3)0.010 (2)−0.018 (2)
C130.064 (3)0.051 (2)0.080 (3)−0.025 (2)0.020 (2)−0.016 (2)
C140.053 (2)0.057 (2)0.087 (3)−0.0197 (19)−0.009 (2)0.000 (2)
C150.054 (2)0.057 (2)0.061 (2)−0.0173 (18)−0.0054 (18)−0.0079 (18)
C160.052 (2)0.051 (2)0.051 (2)−0.0203 (17)−0.0052 (16)0.0026 (16)
C170.054 (2)0.052 (2)0.061 (2)−0.0203 (18)−0.0008 (18)−0.0071 (18)
O30.0510 (16)0.0754 (19)0.0778 (19)−0.0092 (14)−0.0015 (14)0.0076 (15)
C180.054 (3)0.088 (4)0.148 (5)−0.004 (3)0.004 (3)0.003 (4)
C190.089 (11)0.096 (9)0.207 (18)0.014 (7)0.010 (11)−0.036 (9)
C19A0.083 (14)0.159 (19)0.119 (16)−0.017 (14)−0.001 (11)0.041 (13)
C200.050 (2)0.053 (2)0.060 (2)−0.0169 (17)−0.0017 (17)0.0025 (18)
O50.096 (2)0.0653 (18)0.0764 (19)−0.0450 (17)0.0138 (16)−0.0137 (15)
C210.165 (6)0.074 (4)0.132 (5)−0.070 (4)0.049 (5)−0.015 (3)
C220.134 (18)0.069 (8)0.116 (11)−0.042 (9)−0.006 (10)0.000 (7)
C22A0.168 (17)0.117 (12)0.181 (18)−0.080 (13)−0.056 (15)0.053 (11)

Geometric parameters (Å, °)

Se1—C21.836 (4)C14—H140.9300
Se1—N11.875 (4)C15—H150.9300
O1—N31.216 (6)C16—C171.510 (5)
O2—N31.208 (7)C16—C201.525 (5)
O4—C171.195 (5)C16—H160.9800
O6—C201.195 (5)C17—O31.315 (5)
N1—N21.260 (5)O3—C181.447 (5)
N2—C11.386 (5)C18—C191.4991 (10)
N3—C131.472 (6)C18—C19A1.4992 (10)
C1—C21.361 (5)C18—H18A0.9700
C1—C31.476 (5)C18—H18B0.9700
C2—C91.514 (5)C18—H18C0.9700
C3—C81.379 (5)C18—H18D0.9700
C3—C41.392 (5)C19—H19A0.9600
C4—C51.374 (6)C19—H19B0.9600
C4—H40.9300C19—H19C0.9600
C5—C61.366 (7)C19A—H19D0.9600
C5—H50.9300C19A—H19E0.9600
C6—C71.368 (7)C19A—H19F0.9600
C6—H60.9300C20—O51.316 (5)
C7—C81.380 (6)O5—C211.434 (6)
C7—H70.9300C21—C221.4989 (10)
C8—H80.9300C21—C22A1.4990 (10)
C9—C101.517 (5)C21—H21A0.9700
C9—C161.535 (5)C21—H21B0.9700
C9—H90.9800C21—H21C0.9700
C10—C151.378 (5)C21—H21D0.9700
C10—C111.391 (5)C22—H22A0.9600
C11—C121.366 (6)C22—H22B0.9600
C11—H110.9300C22—H22C0.9600
C12—C131.363 (7)C22A—H22D0.9600
C12—H120.9300C22A—H22E0.9600
C13—C141.371 (6)C22A—H22F0.9600
C14—C151.392 (5)
C2—Se1—N187.20 (17)C17—C16—C9111.8 (3)
N2—N1—Se1110.9 (3)C20—C16—C9110.1 (3)
N1—N2—C1117.2 (4)C17—C16—H16108.4
O2—N3—O1123.6 (5)C20—C16—H16108.4
O2—N3—C13117.9 (6)C9—C16—H16108.4
O1—N3—C13118.5 (6)O4—C17—O3124.9 (4)
C2—C1—N2115.9 (4)O4—C17—C16123.6 (4)
C2—C1—C3127.3 (3)O3—C17—C16111.5 (3)
N2—C1—C3116.7 (3)C17—O3—C18117.6 (4)
C1—C2—C9127.6 (3)O3—C18—C19106.1 (6)
C1—C2—Se1108.8 (3)O3—C18—C19A118.2 (9)
C9—C2—Se1123.7 (3)O3—C18—H18A110.5
C8—C3—C4118.5 (4)C19—C18—H18A110.5
C8—C3—C1121.9 (3)O3—C18—H18B110.5
C4—C3—C1119.6 (3)C19—C18—H18B110.5
C5—C4—C3120.7 (4)H18A—C18—H18B108.7
C5—C4—H4119.6O3—C18—H18C107.7
C3—C4—H4119.6C19A—C18—H18C107.7
C6—C5—C4120.2 (4)O3—C18—H18D107.7
C6—C5—H5119.9C19A—C18—H18D107.7
C4—C5—H5119.9H18C—C18—H18D107.1
C5—C6—C7119.5 (5)C18—C19—H19A109.5
C5—C6—H6120.3C18—C19—H19B109.5
C7—C6—H6120.3C18—C19—H19C109.5
C6—C7—C8121.1 (4)C18—C19A—H19D109.5
C6—C7—H7119.4C18—C19A—H19E109.5
C8—C7—H7119.4H19D—C19A—H19E109.5
C3—C8—C7119.8 (4)C18—C19A—H19F109.5
C3—C8—H8120.1H19D—C19A—H19F109.5
C7—C8—H8120.1H19E—C19A—H19F109.5
C2—C9—C10111.3 (3)O6—C20—O5124.2 (4)
C2—C9—C16112.8 (3)O6—C20—C16125.6 (4)
C10—C9—C16112.6 (3)O5—C20—C16110.2 (3)
C2—C9—H9106.5C20—O5—C21115.6 (4)
C10—C9—H9106.5O5—C21—C22112.0 (7)
C16—C9—H9106.5O5—C21—C22A110.3 (8)
C15—C10—C11119.3 (3)O5—C21—H21A109.2
C15—C10—C9121.5 (3)C22—C21—H21A109.2
C11—C10—C9119.1 (3)O5—C21—H21B109.2
C12—C11—C10120.4 (4)C22—C21—H21B109.2
C12—C11—H11119.8H21A—C21—H21B107.9
C10—C11—H11119.8O5—C21—H21C109.6
C13—C12—C11119.4 (4)C22A—C21—H21C109.6
C13—C12—H12120.3O5—C21—H21D109.6
C11—C12—H12120.3C22A—C21—H21D109.6
C12—C13—C14122.2 (4)H21C—C21—H21D108.1
C12—C13—N3119.1 (5)C21—C22—H22A109.5
C14—C13—N3118.7 (5)C21—C22—H22B109.5
C13—C14—C15118.3 (4)C21—C22—H22C109.5
C13—C14—H14120.9C21—C22A—H22D109.5
C15—C14—H14120.9C21—C22A—H22E109.5
C10—C15—C14120.4 (4)H22D—C22A—H22E109.5
C10—C15—H15119.8C21—C22A—H22F109.5
C14—C15—H15119.8H22D—C22A—H22F109.5
C17—C16—C20109.6 (3)H22E—C22A—H22F109.5
C2—Se1—N1—N20.3 (4)C10—C11—C12—C13−0.2 (6)
Se1—N1—N2—C10.3 (6)C11—C12—C13—C14−0.5 (6)
N1—N2—C1—C2−1.0 (6)C11—C12—C13—N3−178.0 (4)
N1—N2—C1—C3−178.4 (4)O2—N3—C13—C12−178.0 (5)
N2—C1—C2—C9−177.9 (4)O1—N3—C13—C121.8 (6)
C3—C1—C2—C9−0.8 (6)O2—N3—C13—C144.4 (6)
N2—C1—C2—Se11.1 (4)O1—N3—C13—C14−175.8 (4)
C3—C1—C2—Se1178.2 (3)C12—C13—C14—C150.9 (6)
N1—Se1—C2—C1−0.8 (3)N3—C13—C14—C15178.4 (4)
N1—Se1—C2—C9178.3 (3)C11—C10—C15—C140.1 (5)
C2—C1—C3—C850.7 (6)C9—C10—C15—C14178.9 (3)
N2—C1—C3—C8−132.2 (4)C13—C14—C15—C10−0.7 (6)
C2—C1—C3—C4−127.9 (4)C2—C9—C16—C17−48.0 (4)
N2—C1—C3—C449.2 (5)C10—C9—C16—C17−175.1 (3)
C8—C3—C4—C5−3.1 (6)C2—C9—C16—C20−170.0 (3)
C1—C3—C4—C5175.6 (4)C10—C9—C16—C2062.9 (4)
C3—C4—C5—C61.7 (7)C20—C16—C17—O4−138.2 (4)
C4—C5—C6—C70.5 (7)C9—C16—C17—O499.5 (5)
C5—C6—C7—C8−1.3 (7)C20—C16—C17—O342.6 (4)
C4—C3—C8—C72.3 (6)C9—C16—C17—O3−79.7 (4)
C1—C3—C8—C7−176.4 (4)O4—C17—O3—C181.7 (6)
C6—C7—C8—C3−0.1 (7)C16—C17—O3—C18−179.0 (4)
C1—C2—C9—C10−128.4 (4)C17—O3—C18—C19105.5 (15)
Se1—C2—C9—C1052.8 (4)C17—O3—C18—C19A149 (2)
C1—C2—C9—C16103.8 (4)C17—C16—C20—O6−118.3 (4)
Se1—C2—C9—C16−75.0 (4)C9—C16—C20—O65.1 (6)
C2—C9—C10—C15−81.3 (4)C17—C16—C20—O562.4 (4)
C16—C9—C10—C1546.6 (4)C9—C16—C20—O5−174.3 (3)
C2—C9—C10—C1197.5 (4)O6—C20—O5—C213.5 (7)
C16—C9—C10—C11−134.6 (3)C16—C20—O5—C21−177.2 (5)
C15—C10—C11—C120.3 (6)C20—O5—C21—C22163.5 (15)
C9—C10—C11—C12−178.5 (4)C20—O5—C21—C22A121.8 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C22A—H22D···O2i0.962.473.38 (4)159
C11—H11···O6ii0.932.563.410 (6)152
C18—H18A···O40.972.292.686 (7)103
C21—H21C···O60.972.172.627 (6)107

Symmetry codes: (i) x−1, y+1, z; (ii) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2278).

References

  • Bertini, V., Dapporto, P., Lucchesini, F., Sega, A. & De Munno, A. (1984). Acta Cryst. C40, 653–655.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • El-Bahaie, S., Assy, M. G. & Hassanien, M. M. (1990). Pharmazie, 45, 791–793. [PubMed]
  • El-Kashef, H. S., E-Bayoumy, B. & Aly, T. I. (1986). Egypt. J. Pharm. Sci.27, 27–30.
  • Gunasekaran, B., Manivannan, V., Saravanan, S., Muthusubramanian, S. & Nethaji, M. (2007). Acta Cryst. E63, o4024.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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