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ISSN: 2056-9890

Ethyl 1,4-bis­­(4-chloro­phen­yl)-2-methyl-1H-pyrrole-3-carboxyl­ate

aDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and cSER-CAT, APS, Argonne National Laboratory, Argonne, IL 60439, USA
*Correspondence e-mail: kmantelingu@yahoo.com

(Received 8 June 2013; accepted 11 July 2013; online 17 July 2013)

In the title mol­ecule, C20H17Cl2NO2, the pyrrole moiety makes dihedral angles of 63.42 (11) and 70.43 (12)° with the chlorobenzene rings. The eth­oxy­carbonyl unit is present in a synperiplanar conformation with respect to the pyrrole ring, as indicated by the dihedral angle of 14.5 (3)°. In the crystal, mol­ecules are linked into chains parallel to the a-axis direction by weak C—H⋯O hydrogen bonds.

Related literature

For the biological importance of pyrroles, see: Banwell et al. (2006[Banwell, M. G., Hamel, E., Hockless, D. C. R., Verdier-Pinard, P., Willis, A. C. & Wong, D. J. (2006). Bioorg. Med. Chem. 14, 4627-4638.]); Mohamed et al. (2009[Mohamed, M. S., El-Domany, R. A. & El-Hameed, R. H. A. (2009). Acta Pharm. 59, 145-158.]); Sosa et al. (2002[Sosa, A. C. B., Yakushijin, K. & Horne, D. A. (2002). J. Org. Chem. 67, 4498-4500.]).

[Scheme 1]

Experimental

Crystal data
  • C20H17Cl2NO2

  • Mr = 374.25

  • Triclinic, [P \overline 1]

  • a = 8.037 (2) Å

  • b = 9.797 (3) Å

  • c = 12.510 (4) Å

  • α = 72.774 (16)°

  • β = 86.838 (16)°

  • γ = 76.804 (16)°

  • V = 915.9 (5) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 296 K

  • 0.15 × 0.15 × 0.15 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS, University of Göttingen, Germany.]) Tmin = 0.947, Tmax = 0.947

  • 15843 measured reflections

  • 4196 independent reflections

  • 2759 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 0.125

  • S = 1.03

  • 4196 reflections

  • 228 parameters

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O8i 0.93 2.58 3.453 (3) 157
C6—H6C⋯O8 0.96 2.42 3.041 (3) 122
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97

Supporting information


Comment top

Pyrrole is a five-membered heterocyclic ring with one nitrogen atom. Its derivatives exhibit a variety of biological activities such as antitumor (Banwell et al., 2006) and antimicrobial (Mohamed et al., 2009) activities. They also inhibit protein kinase (Sosa et al., 2002). With this background of pyrrole derivatives, we have synthesized the title compound in order to study its crystal structure.

In the molecular structure of the title compound (Fig. 1), the dihedral angle between the pyrrole ring (N1/C2/C3/C4/C5) with phenyl rings (C19/C20/C21/C22/C23/C24) and (C12/C13/C14/C15/C16/C17) are 63.42 (11)° and 70.43 (12)°, respectively. The ethoxycarbonyl unit is in syn-periplanar conformation with respect to the pyrrole moiety, as indicated by the dihedral angle value of 14.5 (3)° (C3/C4/C7/O9). There are no classical hydrogen bonds and the crystal structure is stabilized by C—H···O hydrogen bonds only (see Table 1). C6—H6C···O8 forms an intramolecular hydrogen bond, while C2—H2···O8 links molecules which are parallel to the axis a. The packing of the molecules is shown in Fig. 2.

Related literature top

For the biological importance of pyrroles, see: Banwell et al. (2006); Mohamed et al. (2009); Sosa et al. (2002).

Experimental top

To a stirred solution of para-chloroaniline (1.5 mmol), para-chlorobenzaldehyde (1.0 mmol) and ethyl acetoacetate (1.0 mmol) in nitromethane (1.5 ml), ferric chloride (FeCl3) (0.1 mmol) was added. The mixture was refluxed at 90–100°C for 6 hrs and then cooled to room temperature. The excess of solvent was removed under vacuum and the residue was directly purified by column chromatography using 60–120 silica gel with ethyl acetate in hexane (1:9) as eluent which afforded the desired product as yellow solid with 88% yield. The crude product has been recrystallized from hot ethanol. Typical size of the block-shaped crystals was 0.20 × 0.15 × 0.10 mm.

Refinement top

All the H atoms were located in the difference electron density map. Nevertheless all the H atoms were situated into the idealized positions and allowed to ride on their parent atoms with C–H distances equal to 0.93, 0.96 and 0.97Å for aryl, methylene and methyl hydrogens. UisoHaryl/methylene = 1.2UeqCaryl/methylene and Umethyl = 1.5UeqCmethyl

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The title molecule with the labelling scheme. The displacement ellipsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of the molecule viewed parallel to the a axis.
Ethyl 1,4-bis(4-chlorophenyl)-2-methyl-1H-pyrrole-3-carboxylate top
Crystal data top
C20H17Cl2NO2Z = 2
Mr = 374.25F(000) = 388
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.037 (2) ÅCell parameters from 4196 reflections
b = 9.797 (3) Åθ = 1.7–27.5°
c = 12.510 (4) ŵ = 0.37 mm1
α = 72.774 (16)°T = 296 K
β = 86.838 (16)°Block, yellow
γ = 76.804 (16)°0.15 × 0.15 × 0.15 mm
V = 915.9 (5) Å3
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4196 independent reflections
Radiation source: fine-focus sealed tube2759 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and ϕ scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1010
Tmin = 0.947, Tmax = 0.947k = 1212
15843 measured reflectionsl = 1616
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)] = 0.044Hydrogen site location: difference Fourier map
wR(F2) = 0.125H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0487P)2 + 0.2827P]
where P = (Fo2 + 2Fc2)/3
4196 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.29 e Å3
66 constraints
Crystal data top
C20H17Cl2NO2γ = 76.804 (16)°
Mr = 374.25V = 915.9 (5) Å3
Triclinic, P1Z = 2
a = 8.037 (2) ÅMo Kα radiation
b = 9.797 (3) ŵ = 0.37 mm1
c = 12.510 (4) ÅT = 296 K
α = 72.774 (16)°0.15 × 0.15 × 0.15 mm
β = 86.838 (16)°
Data collection top
Bruker SMART APEXII CCD area-detector
diffractometer
4196 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
2759 reflections with I > 2σ(I)
Tmin = 0.947, Tmax = 0.947Rint = 0.032
15843 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å3
4196 reflectionsΔρmin = 0.29 e Å3
228 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Cl180.20768 (10)0.57041 (7)0.24828 (5)0.0884 (2)
Cl250.78934 (10)0.46743 (9)1.16162 (6)0.1057 (3)
O90.18070 (16)0.14269 (16)0.59033 (12)0.0585 (4)
O80.27098 (18)0.0253 (2)0.75691 (13)0.0735 (5)
N10.2589 (2)0.07110 (19)0.83555 (13)0.0521 (4)
C130.1310 (3)0.2004 (2)0.46496 (17)0.0554 (5)
H130.10050.11570.46160.067*
C120.1613 (2)0.2151 (2)0.56891 (15)0.0458 (4)
C30.1594 (2)0.0973 (2)0.67518 (15)0.0470 (4)
C70.1558 (2)0.0648 (2)0.69825 (16)0.0498 (5)
C40.0231 (2)0.0321 (2)0.73283 (15)0.0458 (4)
C150.1876 (3)0.4336 (2)0.37081 (17)0.0562 (5)
C170.2025 (3)0.3436 (2)0.56978 (17)0.0554 (5)
H170.22190.35760.63800.066*
C140.1448 (3)0.3078 (2)0.36672 (17)0.0589 (5)
H140.12510.29490.29820.071*
C190.3838 (2)0.1689 (2)0.91686 (16)0.0505 (5)
C20.2999 (2)0.0304 (2)0.74178 (16)0.0533 (5)
H20.40790.05020.72630.064*
C220.6316 (3)0.3508 (3)1.06663 (17)0.0615 (6)
C160.2157 (3)0.4528 (2)0.47182 (19)0.0640 (6)
H160.24360.53880.47460.077*
C60.0083 (3)0.1721 (3)0.92294 (19)0.0655 (6)
H6A0.00780.13660.98740.098*
H6B0.08160.26840.94260.098*
H6C0.10030.17640.89730.098*
C50.0887 (2)0.0707 (2)0.83166 (16)0.0501 (5)
C230.6287 (3)0.3663 (3)0.9623 (2)0.0794 (8)
H230.71000.43830.94210.095*
C200.3894 (3)0.1548 (3)1.02199 (18)0.0664 (6)
H200.30880.08261.04240.080*
C210.5134 (3)0.2469 (3)1.09782 (18)0.0690 (6)
H210.51620.23811.16970.083*
C240.5039 (3)0.2739 (3)0.88682 (18)0.0721 (7)
H240.50140.28320.81510.087*
C100.3529 (3)0.1775 (3)0.54626 (19)0.0698 (6)
H10A0.42720.24620.57980.084*
H10B0.39720.08940.56300.084*
C110.3464 (3)0.2438 (3)0.4224 (2)0.0822 (8)
H11A0.30130.33030.40680.123*
H11B0.45960.26940.39100.123*
H11C0.27420.17440.39000.123*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl180.1196 (6)0.0733 (4)0.0583 (4)0.0226 (4)0.0054 (3)0.0019 (3)
Cl250.1053 (6)0.1152 (6)0.0738 (4)0.0282 (4)0.0484 (4)0.0242 (4)
O80.0469 (8)0.1037 (13)0.0608 (9)0.0179 (8)0.0010 (7)0.0098 (9)
O90.0441 (7)0.0719 (10)0.0534 (8)0.0092 (7)0.0091 (6)0.0103 (7)
N10.0445 (9)0.0604 (10)0.0448 (9)0.0098 (7)0.0067 (7)0.0056 (8)
C20.0458 (11)0.0623 (13)0.0474 (11)0.0157 (9)0.0044 (8)0.0057 (10)
C30.0447 (10)0.0518 (11)0.0444 (10)0.0085 (8)0.0044 (8)0.0146 (9)
C40.0431 (10)0.0495 (11)0.0440 (10)0.0073 (8)0.0011 (8)0.0143 (9)
C50.0445 (10)0.0551 (12)0.0495 (11)0.0099 (9)0.0014 (8)0.0141 (9)
C60.0567 (13)0.0673 (15)0.0614 (14)0.0137 (11)0.0008 (10)0.0022 (11)
C70.0471 (11)0.0542 (12)0.0470 (11)0.0065 (9)0.0031 (9)0.0163 (9)
C100.0461 (11)0.0895 (17)0.0670 (14)0.0050 (11)0.0159 (10)0.0172 (13)
C110.0730 (16)0.104 (2)0.0638 (15)0.0006 (14)0.0226 (12)0.0256 (14)
C120.0391 (9)0.0498 (11)0.0454 (10)0.0043 (8)0.0050 (7)0.0126 (9)
C130.0609 (12)0.0560 (12)0.0521 (12)0.0145 (10)0.0025 (9)0.0181 (10)
C140.0657 (13)0.0681 (14)0.0432 (11)0.0131 (11)0.0025 (9)0.0177 (10)
C150.0562 (12)0.0538 (12)0.0487 (11)0.0031 (9)0.0008 (9)0.0072 (10)
C160.0803 (15)0.0499 (12)0.0617 (14)0.0140 (11)0.0046 (11)0.0157 (11)
C170.0637 (13)0.0549 (13)0.0474 (11)0.0092 (10)0.0085 (9)0.0161 (10)
C190.0464 (10)0.0563 (12)0.0429 (10)0.0089 (9)0.0073 (8)0.0059 (9)
C200.0676 (14)0.0734 (15)0.0534 (13)0.0026 (11)0.0073 (10)0.0238 (11)
C210.0756 (15)0.0849 (17)0.0443 (11)0.0051 (13)0.0134 (10)0.0225 (12)
C220.0628 (13)0.0675 (14)0.0463 (11)0.0038 (11)0.0170 (9)0.0098 (10)
C230.0809 (16)0.0853 (18)0.0589 (14)0.0205 (13)0.0208 (12)0.0267 (13)
C240.0764 (15)0.0865 (17)0.0474 (12)0.0090 (13)0.0181 (10)0.0275 (12)
Geometric parameters (Å, º) top
Cl18—C151.740 (2)C19—C241.366 (3)
Cl25—C221.739 (3)C20—C211.376 (3)
O8—C71.211 (2)C21—C221.358 (4)
O9—C71.340 (2)C22—C231.360 (3)
O9—C101.447 (3)C23—C241.379 (4)
N1—C21.375 (3)C2—H20.9300
N1—C51.371 (2)C6—H6A0.9600
N1—C191.434 (3)C6—H6B0.9600
C2—C31.357 (3)C6—H6C0.9600
C3—C41.445 (2)C10—H10A0.9700
C3—C121.482 (3)C10—H10B0.9700
C4—C51.383 (3)C11—H11A0.9600
C4—C71.461 (2)C11—H11B0.9600
C5—C61.499 (3)C11—H11C0.9600
C10—C111.495 (3)C13—H130.9300
C12—C131.390 (3)C14—H140.9300
C12—C171.376 (3)C16—H160.9300
C13—C141.379 (3)C17—H170.9300
C14—C151.369 (3)C20—H200.9300
C15—C161.369 (3)C21—H210.9300
C16—C171.385 (3)C23—H230.9300
C19—C201.367 (3)C24—H240.9300
Cl18···C21i3.505 (3)C10···H2v3.0500
Cl18···H23ii3.0100C10···H16vii3.0400
Cl25···H17iii3.0000C11···H16vii3.0700
O8···C63.041 (3)C15···H11Bx2.9100
O8···C20iv3.377 (3)C17···H10Ax2.9100
O9···C122.971 (2)C19···H6B2.7900
O9···C132.957 (3)H2···O8x2.5800
O8···H10A2.7200H2···C10x3.0500
O8···H10B2.5300H2···H10Bx2.5000
O8···H20iv2.7200H6B···C192.7900
O8···H21iv2.8500H6C···O82.4200
O8···H2v2.5800H6C···C72.8500
O8···H6C2.4200H10A···O82.7200
O9···H132.7100H10A···C17v2.9100
O9···H13vi2.7300H10B···O82.5300
O9···H16vii2.9100H10B···H2v2.5000
C6···O83.041 (3)H11A···H16vii2.3500
C6···C203.424 (4)H11B···C15v2.9100
C12···O92.971 (2)H11B···H24vi2.5800
C13···O92.957 (3)H11C···C2vi3.0000
C15···C17vii3.567 (3)H11C···C3vi2.9500
C16···C17vii3.473 (3)H13···O92.7100
C16···C16vii3.468 (4)H13···O9vi2.7300
C17···C15vii3.567 (3)H13···C7vi2.9900
C17···C16vii3.473 (3)H16···O9vii2.9100
C20···O8iv3.377 (3)H16···C10vii3.0400
C20···C63.424 (4)H16···C11vii3.0700
C21···Cl18viii3.505 (3)H16···H11Avii2.3500
C23···C23ix3.582 (4)H17···C23.0100
C2···H11Cvi3.0000H17···Cl25iii3.0000
C2···H243.0200H20···O8iv2.7200
C2···H173.0100H21···O8iv2.8500
C3···H11Cvi2.9500H23···Cl18ii3.0100
C7···H13vi2.9900H24···C23.0200
C7···H6C2.8500H24···H11Bvi2.5800
C7—O9—C10116.77 (15)C19—C24—C23120.4 (2)
C2—N1—C5109.47 (16)N1—C2—H2125.00
C2—N1—C19122.99 (16)C3—C2—H2125.00
C5—N1—C19127.29 (16)C5—C6—H6A109.00
N1—C2—C3109.90 (16)C5—C6—H6B109.00
C2—C3—C4105.42 (16)C5—C6—H6C109.00
C2—C3—C12122.85 (16)H6A—C6—H6B109.00
C4—C3—C12131.70 (16)H6A—C6—H6C110.00
C3—C4—C5108.37 (15)H6B—C6—H6C109.00
C3—C4—C7128.27 (17)O9—C10—H10A110.00
C5—C4—C7123.36 (16)O9—C10—H10B110.00
N1—C5—C4106.84 (16)C11—C10—H10A110.00
N1—C5—C6121.23 (18)C11—C10—H10B110.00
C4—C5—C6131.92 (17)H10A—C10—H10B108.00
O8—C7—O9122.15 (17)C10—C11—H11A109.00
O8—C7—C4125.71 (18)C10—C11—H11B109.00
O9—C7—C4112.13 (15)C10—C11—H11C109.00
O9—C10—C11107.67 (19)H11A—C11—H11B109.00
C3—C12—C13123.03 (18)H11A—C11—H11C110.00
C3—C12—C17119.97 (17)H11B—C11—H11C110.00
C13—C12—C17116.92 (18)C12—C13—H13119.00
C12—C13—C14121.90 (19)C14—C13—H13119.00
C13—C14—C15119.53 (19)C13—C14—H14120.00
Cl18—C15—C14120.60 (16)C15—C14—H14120.00
Cl18—C15—C16119.25 (17)C15—C16—H16120.00
C14—C15—C16120.15 (19)C17—C16—H16120.00
C15—C16—C17119.7 (2)C12—C17—H17119.00
C12—C17—C16121.80 (19)C16—C17—H17119.00
N1—C19—C20121.23 (19)C19—C20—H20120.00
N1—C19—C24119.19 (18)C21—C20—H20120.00
C20—C19—C24119.5 (2)C20—C21—H21120.00
C19—C20—C21120.4 (2)C22—C21—H21120.00
C20—C21—C22119.3 (2)C22—C23—H23120.00
Cl25—C22—C21119.70 (17)C24—C23—H23120.00
Cl25—C22—C23119.1 (2)C19—C24—H24120.00
C21—C22—C23121.2 (2)C23—C24—H24120.00
C22—C23—C24119.2 (3)
C10—O9—C7—O80.2 (3)C7—C4—C5—C61.5 (4)
C10—O9—C7—C4178.21 (19)C3—C4—C7—O8167.2 (2)
C7—O9—C10—C11171.6 (2)C3—C4—C7—O914.5 (3)
C5—N1—C2—C30.5 (2)C5—C4—C7—O812.2 (3)
C19—N1—C2—C3174.18 (18)C5—C4—C7—O9166.22 (19)
C2—N1—C5—C40.6 (2)C3—C12—C13—C14175.6 (2)
C2—N1—C5—C6179.4 (2)C17—C12—C13—C141.3 (3)
C19—N1—C5—C4173.79 (19)C3—C12—C17—C16176.1 (2)
C19—N1—C5—C65.0 (3)C13—C12—C17—C160.9 (3)
C2—N1—C19—C20110.8 (2)C12—C13—C14—C150.8 (4)
C2—N1—C19—C2466.3 (3)C13—C14—C15—Cl18179.48 (19)
C5—N1—C19—C2075.4 (3)C13—C14—C15—C160.3 (4)
C5—N1—C19—C24107.5 (2)Cl18—C15—C16—C17179.05 (19)
N1—C2—C3—C40.2 (2)C14—C15—C16—C170.7 (4)
N1—C2—C3—C12178.42 (18)C15—C16—C17—C120.1 (4)
C2—C3—C4—C50.2 (2)N1—C19—C20—C21178.0 (2)
C2—C3—C4—C7179.6 (2)C24—C19—C20—C211.0 (4)
C12—C3—C4—C5177.8 (2)N1—C19—C24—C23177.9 (2)
C12—C3—C4—C71.6 (4)C20—C19—C24—C230.8 (4)
C2—C3—C12—C13116.0 (2)C19—C20—C21—C220.9 (4)
C2—C3—C12—C1760.8 (3)C20—C21—C22—Cl25179.8 (2)
C4—C3—C12—C1366.3 (3)C20—C21—C22—C230.6 (4)
C4—C3—C12—C17116.9 (2)Cl25—C22—C23—C24179.9 (2)
C3—C4—C5—N10.5 (2)C21—C22—C23—C240.5 (4)
C3—C4—C5—C6179.1 (2)C22—C23—C24—C190.6 (4)
C7—C4—C5—N1179.95 (18)
Symmetry codes: (i) x, y+1, z1; (ii) x+1, y, z+1; (iii) x+1, y, z+2; (iv) x, y, z+2; (v) x1, y, z; (vi) x, y, z+1; (vii) x, y+1, z+1; (viii) x, y1, z+1; (ix) x+1, y1, z+2; (x) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O8x0.932.583.453 (3)157
C6—H6C···O80.962.423.041 (3)122
Symmetry code: (x) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O8i0.93002.58003.453 (3)157.00
C6—H6C···O80.96002.42003.041 (3)122.00
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

C and KNN would like to thank the University of Mysore for awarding RFSMS fellowships [DV5/Physics/389/RFSMS/2009–2010/10.07.2012 and No. F4–1/2006(BSR)/7–131/2007, respectively].

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