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Acta Cryst. (2007). E63, o3680    [ doi:10.1107/S1600536807037063 ]

(2E)-1-(4-Methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one

R. J. Butcher, J. P. Jasinski, H. S. Yathirajan, K. Veena and B. Narayana

Abstract top

The title compound, C16H13NO3, crystallizes with two nearly planar independent molecules in the asymmetric unit. The molecules exist as pseudo-inversion-related pairs and each of the independent molecules forms sheets approximately parallel to the ab plane which are alternately stacked along the c axis. The crystal structure is stabilized by C-H...O intermolecular hydrogen-bonding interactions.

Comment top

Chalcone is an aromatic ketone that forms a central core for a variety of important biological compounds, which are known collectively as chalcones. Chalcones and the corresponding heterocyclic analogs are valuable intermediates in organic synthesis and show numerous biological effects. The non-linear optical (NLO) effects in organic molecules originates from a strong donor–acceptor intermolecular interaction, a delocalized π electron system and also the ability to crystallize in non-centro symmetric space groups. Chalcones are finding applications as organic non-linear optical materials due to their good SHG conversion efficiencies. Herein we report the synthesis and crystal structure of a new chalcone, the title compound.

The asymmetric unit of the title compound contains two independent molecules A and B both of which are shown in Fig. 1. The C9—C8—C1—C6 and C9—C10—C11—C12 torsion angles [(A) −0.8 (5), 6.4 (5)°; (B) 5.2 (4), −8.2 (5)°] indicate that the 4-methylphenyl and 4-nitrophenyl groups are slightly twisted with respect to the central O1/C8—C11 plane.

In the crystal structure, the independent molecues exist as a pseudo inversion-related pair with the centroids of the 4-methylphenyl and 4-nitrophenyl rings separated by a distance of 3.7550 (17) Å, indicating π-π stacking interaction. Crystal packing shows each of these independent molecules form sheets approximately parallel to the ab plane (Fig. 2). The sheets formed by these molecules are alternatively stacked along the c axis and are cross-linked by C—H···O intermolecular hydrogen-bonding interactions (Table 1).

Related literature top

For related structures, see: Yathirajan et al. (2007); Harrison et al. (2006); Patil et al. (2006). For related literature, see: Dhar et al. (1981); Opletalova & Sedivy et al. (1999); Sarojini et al. (2006).

Experimental top

4-Nitrobenzaldehyde (1.81 g, 0.01 mol) in ethanol (50 ml) was mixed with 1-(4-methyl phenyl) ethanone (1.34 ml, 0.01 mol) and the mixture was treated with 10 ml of 10% KOH. The reaction mixture was then kept for constant stirring. The solid precipitate obtained was filtered, washed with ethanol and dried. The crystal growth was carried out in acetone solvent by the slow evaporation technique (m.p. 435 K). Analysis found: C 71.78, H 4.83, N 5.18%; C16H13NO3 requires: C 71.90, H 4.90, N 5.24%.

Refinement top

All H atoms were refined using a riding model with C—H = 0.94–0.97 Å, and Uiso(H) = 1.18–1.50Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Computing details top

Data collection: CrysAlisPro (Oxford Diffraction, 2007); cell refinement: CrysAlisPro; data reduction: CrysAlisPro; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules (A and B) forming the asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed down the a axis. Dashed lines indicate C—H···O hydrogen bonds.
(2E)-1-(4-Methylphenyl)-3-(4-nitrophenyl)prop-2-en-1-one top
Crystal data top
C16H13NO3F000 = 560
Mr = 267.27Dx = 1.350 Mg m−3
Monoclinic, PcMo Kα radiation
λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 10389 reflections
a = 5.97300 (1) Åθ = 4.6–32.4º
b = 15.0731 (5) ŵ = 0.09 mm−1
c = 14.6768 (4) ÅT = 203 K
β = 95.785 (2)ºBlock, colourless
V = 1314.65 (6) Å30.47 × 0.41 × 0.29 mm
Z = 4
Data collection top
Oxford Diffraction Gemini R
diffractometer		4496 independent reflections
Radiation source: fine-focus sealed tube2661 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.051
T = 203 Kθmax = 32.5º
φ and ω scansθmin = 4.6º
Absorption correction: multi-scan
(CrysAlisRED; Oxford Diffraction, 2007)		h = −8→9
Tmin = 0.955, Tmax = 1.000k = −22→21
37695 measured reflectionsl = −21→22
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055  w = 1/[σ2(Fo2) + (0.0728P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162(Δ/σ)max = 0.001
S = 1.25Δρmax = 0.23 e Å−3
4496 reflectionsΔρmin = −0.23 e Å−3
363 parametersExtinction correction: none
2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Crystal data top
C16H13NO3V = 1314.65 (6) Å3
Mr = 267.27Z = 4
Monoclinic, PcMo Kα
a = 5.97300 (1) ŵ = 0.09 mm−1
b = 15.0731 (5) ÅT = 203 K
c = 14.6768 (4) Å0.47 × 0.41 × 0.29 mm
β = 95.785 (2)º
Data collection top
Oxford Diffraction Gemini R
diffractometer		4496 independent reflections
Absorption correction: multi-scan
(CrysAlisRED; Oxford Diffraction, 2007)		2661 reflections with I > 2σ(I)
Tmin = 0.955, Tmax = 1.000Rint = 0.051
37695 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.162Δρmax = 0.23 e Å−3
S = 1.25Δρmin = −0.23 e Å−3
4496 reflectionsAbsolute structure: ?
363 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
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 > 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
O1A0.5810 (4)0.15276 (19)0.3609 (2)0.0598 (7)
O2A−0.5435 (4)0.5503 (2)0.1891 (2)0.0638 (7)
O3A−0.2876 (5)0.6415 (2)0.2422 (2)0.0717 (9)
N1A−0.3572 (5)0.5665 (2)0.22697 (19)0.0434 (7)
C1A0.3401 (6)0.0319 (3)0.3272 (2)0.0377 (7)
C2A0.5097 (5)−0.0293 (3)0.3529 (2)0.0434 (8)
H2A0.6549−0.00890.37320.052*
C3A0.4681 (6)−0.1196 (3)0.3492 (3)0.0501 (9)
H3A0.5850−0.15940.36760.060*
C4A0.2560 (5)−0.1524 (2)0.3185 (2)0.0406 (8)
C5A0.0874 (6)−0.0926 (3)0.2929 (2)0.0452 (9)
H5A−0.0568−0.11360.27180.054*
C6A0.1261 (5)−0.0018 (2)0.2977 (2)0.0431 (8)
H6A0.00720.03760.28090.052*
C7A0.2110 (7)−0.2512 (3)0.3134 (3)0.0546 (9)
H7A0.0911−0.26310.26540.082*
H7B0.1665−0.27170.37160.082*
H7C0.3464−0.28200.30010.082*
C8A0.3919 (5)0.1278 (2)0.3334 (2)0.0394 (7)
C9A0.2096 (5)0.1932 (3)0.3060 (2)0.0403 (8)
H9A0.07350.17380.27460.048*
C10A0.2392 (5)0.2787 (2)0.3258 (2)0.0382 (7)
H10A0.37730.29480.35790.046*
C11A0.0756 (5)0.3511 (2)0.30221 (19)0.0349 (7)
C12A−0.1442 (5)0.3358 (2)0.2625 (2)0.0400 (7)
H12A−0.19490.27720.25230.048*
C13A−0.2877 (5)0.4058 (3)0.2381 (2)0.0408 (8)
H13A−0.43480.39570.21100.049*
C14A−0.2081 (5)0.4915 (2)0.2549 (2)0.0371 (7)
C15A0.0033 (5)0.5092 (2)0.2955 (2)0.0407 (7)
H15A0.05160.56790.30690.049*
C16A0.1458 (5)0.4373 (2)0.3197 (2)0.0404 (7)
H16A0.29140.44790.34820.048*
O1B−0.3940 (4)0.40110 (19)0.4712 (2)0.0581 (7)
O2B0.7162 (4)−0.0017 (2)0.6455 (2)0.0614 (8)
O3B0.4447 (5)−0.0907 (2)0.6053 (2)0.0647 (8)
N1B0.5230 (5)−0.0162 (2)0.61432 (18)0.0430 (7)
C1B−0.1587 (5)0.5225 (2)0.51618 (18)0.0326 (6)
C2B−0.3283 (6)0.5826 (3)0.4924 (2)0.0404 (8)
H2B−0.47140.56180.46950.048*
C3B−0.2924 (5)0.6731 (2)0.5014 (2)0.0444 (8)
H3B−0.41240.71250.48620.053*
C4B−0.0826 (5)0.7064 (3)0.5323 (2)0.0399 (8)
C5B0.0894 (5)0.6454 (2)0.5563 (2)0.0416 (7)
H5B0.23290.66620.57860.050*
C6B0.0532 (5)0.5552 (3)0.5479 (2)0.0391 (8)
H6B0.17230.51550.56380.047*
C7B−0.0428 (6)0.8042 (3)0.5426 (3)0.0533 (9)
H7D0.10680.81460.57300.080*
H7E−0.15380.82960.57890.080*
H7F−0.05570.83190.48260.080*
C8B−0.2056 (5)0.4258 (3)0.5051 (2)0.0378 (8)
C9B−0.0307 (5)0.3598 (3)0.5351 (2)0.0411 (8)
H9B0.10330.37850.56880.049*
C10B−0.0609 (5)0.2744 (2)0.5152 (2)0.0375 (7)
H10B−0.19700.25880.48120.045*
C11B0.0964 (5)0.2023 (2)0.54079 (19)0.0353 (7)
C12B0.3171 (5)0.2161 (2)0.5814 (2)0.0416 (8)
H12B0.36990.27430.59260.050*
C13B0.4571 (5)0.1451 (2)0.6050 (2)0.0407 (7)
H13B0.60430.15460.63240.049*
C14B0.3778 (5)0.0600 (2)0.5879 (2)0.0358 (7)
C15B0.1615 (5)0.0439 (3)0.5465 (2)0.0422 (8)
H15B0.1097−0.01430.53510.051*
C16B0.0267 (5)0.1153 (2)0.5227 (2)0.0399 (7)
H16B−0.11820.10530.49320.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0407 (13)0.0393 (16)0.0947 (19)−0.0026 (11)−0.0155 (12)−0.0039 (13)
O2A0.0416 (15)0.062 (2)0.0841 (18)0.0046 (12)−0.0106 (12)0.0084 (15)
O3A0.0562 (16)0.0420 (18)0.112 (2)0.0054 (14)−0.0137 (15)0.0037 (17)
N1A0.0383 (15)0.0412 (19)0.0508 (15)0.0056 (13)0.0050 (12)0.0063 (13)
C1A0.0336 (16)0.039 (2)0.0403 (15)−0.0015 (14)0.0033 (12)−0.0021 (14)
C2A0.0300 (16)0.039 (2)0.0592 (19)0.0030 (14)−0.0058 (13)−0.0014 (16)
C3A0.0412 (19)0.043 (2)0.064 (2)0.0060 (17)−0.0044 (15)0.0048 (18)
C4A0.0415 (18)0.035 (2)0.0452 (16)0.0005 (14)0.0045 (13)0.0006 (13)
C5A0.0380 (18)0.041 (2)0.0547 (18)−0.0036 (16)−0.0031 (14)−0.0006 (17)
C6A0.0342 (17)0.035 (2)0.0581 (19)0.0046 (14)−0.0037 (13)−0.0031 (15)
C7A0.063 (2)0.037 (2)0.064 (2)−0.0034 (19)0.0048 (17)0.0001 (17)
C8A0.0384 (16)0.0322 (19)0.0460 (16)0.0023 (14)−0.0042 (12)0.0004 (13)
C9A0.0396 (18)0.033 (2)0.0454 (17)−0.0021 (15)−0.0077 (13)−0.0009 (14)
C10A0.0397 (16)0.0355 (19)0.0385 (14)0.0016 (14)−0.0003 (11)−0.0018 (13)
C11A0.0342 (16)0.0344 (19)0.0361 (14)0.0011 (13)0.0035 (11)0.0015 (13)
C12A0.0357 (16)0.036 (2)0.0477 (16)−0.0062 (14)0.0012 (12)−0.0008 (14)
C13A0.0304 (16)0.043 (2)0.0489 (17)−0.0010 (15)0.0036 (13)−0.0004 (15)
C14A0.0365 (17)0.036 (2)0.0387 (15)0.0028 (14)0.0059 (12)0.0025 (12)
C15A0.0383 (17)0.0344 (19)0.0497 (17)−0.0026 (14)0.0053 (13)0.0016 (14)
C16A0.0380 (16)0.039 (2)0.0434 (15)−0.0029 (14)−0.0007 (12)−0.0038 (14)
O1B0.0446 (14)0.0446 (16)0.0805 (17)−0.0035 (11)−0.0155 (11)−0.0055 (13)
O2B0.0337 (14)0.059 (2)0.0889 (18)0.0037 (11)−0.0074 (12)0.0012 (15)
O3B0.0501 (15)0.0375 (17)0.103 (2)0.0023 (13)−0.0084 (14)0.0014 (15)
N1B0.0379 (16)0.0441 (19)0.0466 (14)0.0029 (13)0.0023 (11)0.0020 (13)
C1B0.0334 (15)0.0319 (18)0.0324 (13)0.0010 (12)0.0033 (11)0.0017 (11)
C2B0.0330 (16)0.040 (2)0.0464 (16)−0.0027 (14)−0.0040 (12)0.0011 (15)
C3B0.0374 (17)0.039 (2)0.0555 (18)0.0049 (14)−0.0016 (13)0.0005 (15)
C4B0.0392 (17)0.038 (2)0.0431 (16)−0.0012 (14)0.0075 (13)0.0024 (14)
C5B0.0294 (15)0.044 (2)0.0506 (17)0.0007 (14)−0.0016 (12)−0.0020 (15)
C6B0.0310 (16)0.039 (2)0.0463 (17)−0.0012 (14)0.0000 (12)−0.0025 (15)
C7B0.051 (2)0.034 (2)0.074 (2)−0.0020 (17)0.0044 (16)−0.0014 (17)
C8B0.0429 (18)0.036 (2)0.0335 (14)−0.0028 (14)−0.0014 (12)−0.0014 (13)
C9B0.0372 (17)0.040 (2)0.0441 (16)0.0010 (14)−0.0043 (12)−0.0034 (14)
C10B0.0359 (16)0.036 (2)0.0399 (15)−0.0008 (14)0.0022 (12)0.0054 (14)
C11B0.0387 (16)0.0319 (18)0.0354 (14)0.0000 (13)0.0040 (11)0.0009 (12)
C12B0.0387 (17)0.0340 (18)0.0518 (18)−0.0049 (14)0.0035 (13)−0.0021 (14)
C13B0.0352 (16)0.041 (2)0.0452 (16)−0.0061 (14)−0.0004 (12)−0.0043 (14)
C14B0.0323 (16)0.0385 (19)0.0364 (14)0.0010 (14)0.0022 (12)0.0000 (13)
C15B0.0373 (18)0.037 (2)0.0509 (18)−0.0033 (14)−0.0028 (13)−0.0052 (15)
C16B0.0334 (16)0.037 (2)0.0480 (16)−0.0073 (14)−0.0030 (12)−0.0027 (14)
Geometric parameters (Å, °) top
O1A—C8A1.220 (4)O1B—C8B1.240 (4)
O2A—N1A1.218 (4)O2B—N1B1.217 (4)
O3A—N1A1.217 (4)O3B—N1B1.219 (4)
N1A—C14A1.472 (4)N1B—C14B1.468 (5)
C1A—C2A1.394 (5)C1B—C2B1.378 (5)
C1A—C6A1.403 (5)C1B—C6B1.394 (5)
C1A—C8A1.479 (5)C1B—C8B1.490 (5)
C2A—C3A1.383 (5)C2B—C3B1.385 (5)
C2A—H2A0.94C2B—H2B0.94
C3A—C4A1.392 (5)C3B—C4B1.384 (5)
C3A—H3A0.94C3B—H3B0.94
C4A—C5A1.376 (5)C4B—C5B1.397 (5)
C4A—C7A1.513 (5)C4B—C7B1.499 (5)
C5A—C6A1.388 (5)C5B—C6B1.380 (5)
C5A—H5A0.94C5B—H5B0.94
C6A—H6A0.94C6B—H6B0.94
C7A—H7A0.97C7B—H7D0.97
C7A—H7B0.97C7B—H7E0.97
C7A—H7C0.97C7B—H7F0.97
C8A—C9A1.494 (5)C8B—C9B1.476 (5)
C9A—C10A1.328 (5)C9B—C10B1.329 (5)
C9A—H9A0.94C9B—H9B0.94
C10A—C11A1.482 (5)C10B—C11B1.461 (5)
C10A—H10A0.94C10B—H10B0.94
C11A—C16A1.382 (5)C11B—C16B1.394 (5)
C11A—C12A1.401 (4)C11B—C12B1.407 (5)
C12A—C13A1.384 (5)C12B—C13B1.380 (5)
C12A—H12A0.94C12B—H12B0.94
C13A—C14A1.390 (5)C13B—C14B1.381 (5)
C13A—H13A0.94C13B—H13B0.94
C14A—C15A1.367 (5)C14B—C15B1.393 (5)
C15A—C16A1.401 (5)C15B—C16B1.367 (5)
C15A—H15A0.94C15B—H15B0.94
C16A—H16A0.94C16B—H16B0.94
O2A—N1A—O3A123.4 (3)O2B—N1B—O3B123.0 (3)
O2A—N1A—C14A118.2 (3)O2B—N1B—C14B118.1 (3)
O3A—N1A—C14A118.4 (3)O3B—N1B—C14B118.9 (3)
C2A—C1A—C6A117.3 (3)C2B—C1B—C6B118.1 (3)
C2A—C1A—C8A119.2 (3)C2B—C1B—C8B119.4 (3)
C6A—C1A—C8A123.5 (3)C6B—C1B—C8B122.5 (3)
C3A—C2A—C1A121.2 (3)C1B—C2B—C3B121.4 (3)
C3A—C2A—H2A119.4C1B—C2B—H2B119.3
C1A—C2A—H2A119.4C3B—C2B—H2B119.3
C2A—C3A—C4A121.1 (3)C2B—C3B—C4B121.0 (3)
C2A—C3A—H3A119.5C2B—C3B—H3B119.5
C4A—C3A—H3A119.5C4B—C3B—H3B119.5
C5A—C4A—C3A118.2 (3)C3B—C4B—C5B117.6 (3)
C5A—C4A—C7A120.6 (3)C3B—C4B—C7B121.3 (3)
C3A—C4A—C7A121.1 (3)C5B—C4B—C7B121.1 (3)
C4A—C5A—C6A121.2 (3)C6B—C5B—C4B121.4 (3)
C4A—C5A—H5A119.4C6B—C5B—H5B119.3
C6A—C5A—H5A119.4C4B—C5B—H5B119.3
C5A—C6A—C1A121.0 (3)C5B—C6B—C1B120.5 (3)
C5A—C6A—H6A119.5C5B—C6B—H6B119.8
C1A—C6A—H6A119.5C1B—C6B—H6B119.8
C4A—C7A—H7A109.5C4B—C7B—H7D109.5
C4A—C7A—H7B109.5C4B—C7B—H7E109.5
H7A—C7A—H7B109.5H7D—C7B—H7E109.5
C4A—C7A—H7C109.5C4B—C7B—H7F109.5
H7A—C7A—H7C109.5H7D—C7B—H7F109.5
H7B—C7A—H7C109.5H7E—C7B—H7F109.5
O1A—C8A—C1A120.2 (3)O1B—C8B—C9B120.3 (3)
O1A—C8A—C9A120.7 (3)O1B—C8B—C1B119.3 (3)
C1A—C8A—C9A119.1 (3)C9B—C8B—C1B120.4 (3)
C10A—C9A—C8A120.3 (3)C10B—C9B—C8B120.7 (3)
C10A—C9A—H9A119.9C10B—C9B—H9B119.7
C8A—C9A—H9A119.9C8B—C9B—H9B119.7
C9A—C10A—C11A126.4 (3)C9B—C10B—C11B126.5 (3)
C9A—C10A—H10A116.8C9B—C10B—H10B116.7
C11A—C10A—H10A116.8C11B—C10B—H10B116.7
C16A—C11A—C12A119.1 (3)C16B—C11B—C12B118.0 (3)
C16A—C11A—C10A117.9 (3)C16B—C11B—C10B118.6 (3)
C12A—C11A—C10A123.0 (3)C12B—C11B—C10B123.4 (3)
C13A—C12A—C11A120.8 (3)C13B—C12B—C11B120.6 (3)
C13A—C12A—H12A119.6C13B—C12B—H12B119.7
C11A—C12A—H12A119.6C11B—C12B—H12B119.7
C12A—C13A—C14A118.1 (3)C14B—C13B—C12B119.1 (3)
C12A—C13A—H13A120.9C14B—C13B—H13B120.4
C14A—C13A—H13A120.9C12B—C13B—H13B120.4
C15A—C14A—C13A122.9 (3)C13B—C14B—C15B121.8 (3)
C15A—C14A—N1A118.6 (3)C13B—C14B—N1B119.7 (3)
C13A—C14A—N1A118.5 (3)C15B—C14B—N1B118.4 (3)
C14A—C15A—C16A118.1 (3)C16B—C15B—C14B118.1 (3)
C14A—C15A—H15A121.0C16B—C15B—H15B121.0
C16A—C15A—H15A121.0C14B—C15B—H15B121.0
C11A—C16A—C15A121.0 (3)C15B—C16B—C11B122.3 (3)
C11A—C16A—H16A119.5C15B—C16B—H16B118.8
C15A—C16A—H16A119.5C11B—C16B—H16B118.8
C6A—C1A—C2A—C3A0.2 (5)C6B—C1B—C2B—C3B−1.4 (5)
C8A—C1A—C2A—C3A179.3 (3)C8B—C1B—C2B—C3B−179.9 (3)
C1A—C2A—C3A—C4A0.8 (5)C1B—C2B—C3B—C4B1.8 (5)
C2A—C3A—C4A—C5A−0.7 (5)C2B—C3B—C4B—C5B−1.6 (5)
C2A—C3A—C4A—C7A179.4 (3)C2B—C3B—C4B—C7B−179.7 (3)
C3A—C4A—C5A—C6A−0.2 (5)C3B—C4B—C5B—C6B1.2 (5)
C7A—C4A—C5A—C6A179.7 (3)C7B—C4B—C5B—C6B179.2 (3)
C4A—C5A—C6A—C1A1.2 (5)C4B—C5B—C6B—C1B−0.9 (5)
C2A—C1A—C6A—C5A−1.2 (5)C2B—C1B—C6B—C5B0.9 (5)
C8A—C1A—C6A—C5A179.8 (3)C8B—C1B—C6B—C5B179.4 (3)
C2A—C1A—C8A—O1A−0.1 (5)C2B—C1B—C8B—O1B2.9 (4)
C6A—C1A—C8A—O1A179.0 (3)C6B—C1B—C8B—O1B−175.6 (3)
C2A—C1A—C8A—C9A−179.8 (3)C2B—C1B—C8B—C9B−176.4 (3)
C6A—C1A—C8A—C9A−0.8 (5)C6B—C1B—C8B—C9B5.2 (4)
O1A—C8A—C9A—C10A−11.7 (5)O1B—C8B—C9B—C10B9.2 (5)
C1A—C8A—C9A—C10A168.1 (3)C1B—C8B—C9B—C10B−171.5 (3)
C8A—C9A—C10A—C11A179.2 (3)C8B—C9B—C10B—C11B−179.7 (3)
C9A—C10A—C11A—C16A−173.0 (3)C9B—C10B—C11B—C16B173.0 (3)
C9A—C10A—C11A—C12A6.4 (5)C9B—C10B—C11B—C12B−8.2 (5)
C16A—C11A—C12A—C13A2.1 (4)C16B—C11B—C12B—C13B−1.9 (4)
C10A—C11A—C12A—C13A−177.2 (3)C10B—C11B—C12B—C13B179.3 (3)
C11A—C12A—C13A—C14A−0.5 (4)C11B—C12B—C13B—C14B0.2 (4)
C12A—C13A—C14A—C15A−1.1 (5)C12B—C13B—C14B—C15B0.8 (5)
C12A—C13A—C14A—N1A178.3 (3)C12B—C13B—C14B—N1B−178.7 (3)
O2A—N1A—C14A—C15A178.5 (3)O2B—N1B—C14B—C13B−4.7 (4)
O3A—N1A—C14A—C15A−1.0 (4)O3B—N1B—C14B—C13B174.3 (3)
O2A—N1A—C14A—C13A−1.0 (4)O2B—N1B—C14B—C15B175.7 (3)
O3A—N1A—C14A—C13A179.6 (3)O3B—N1B—C14B—C15B−5.3 (4)
C13A—C14A—C15A—C16A1.1 (5)C13B—C14B—C15B—C16B−0.1 (5)
N1A—C14A—C15A—C16A−178.3 (3)N1B—C14B—C15B—C16B179.5 (3)
C12A—C11A—C16A—C15A−2.1 (4)C14B—C15B—C16B—C11B−1.7 (5)
C10A—C11A—C16A—C15A177.3 (3)C12B—C11B—C16B—C15B2.7 (5)
C14A—C15A—C16A—C11A0.6 (5)C10B—C11B—C16B—C15B−178.4 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O2Bi0.942.563.144 (4)120
C6B—H6B···O2Aii0.942.573.409 (4)148
C7B—H7D···O3Biii0.972.483.361 (5)151
C16A—H16A···O1Biv0.942.573.401 (4)148
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y+1, z+1/2; (iii) x, y+1, z; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C6A—H6A···O2Bi0.942.563.144 (4)120
C6B—H6B···O2Aii0.942.573.409 (4)148
C7B—H7D···O3Biii0.972.483.361 (5)151
C16A—H16A···O1Biv0.942.573.401 (4)148
Symmetry codes: (i) x−1, −y, z−1/2; (ii) x+1, −y+1, z+1/2; (iii) x, y+1, z; (iv) x+1, y, z.
Acknowledgements top

kV thanks Mangalore University for use of their research facilities. RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase the diffractometer.

references
References top

Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: Wiley Interscience.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Harrison, W. T. A., Yathirajan, H. S., Mithun, A., Narayana, B. & Sarojini, B. K. (2006). Acta Cryst. E62, o4508–o4509.

Opletalova, V. & Sedivy, D. (1999). Ceska Slov. Farm. 48, 252–255.

Oxford Diffraction (2007). CrysAlisPro (Version 171.31.8) and CrysAlis RED (Version 1.171.31.8). Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

Patil, P. S., Teh, J. B.-J., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2006). Acta Cryst. E62, o896–o898.

Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. J. (2006). J. Cryst. Growth, 295, 54–59.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Yathirajan, H. S., Mayekar, A. N., Sarojini, B. K., Narayana, B. & Bolte, M. (2007). Acta Cryst. E63, o424–o425.