3 (4 Bromophenyl) 1 (4 nitrophenyl)prop 2 en 1 one

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organic papers

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Rosliet al. _C

15H10BrNO3 doi:10.1107/S1600536806009263 Acta Cryst.(2006). E62, o1466–o1468 Acta Crystallographica Section E

Structure Reports

Online

ISSN 1600-5368

3-(4-Bromophenyl)-1-(4-nitrophenyl)-prop-2-en-1-one

Mohd Mustaqim Rosli,a P. S. Patil,bHoong-Kun Fun,a* Ibrahim Abdul Razakaand S. M. Dharmaprakashb

a_{X-Ray Crystallography Unit, School of Physics,} Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, andb_{Department of Studies in} Physics, Mangalore University,

Mangalagangotri, Mangalore 574 199, India

Correspondence e-mail: [email protected]

Key indicators

Single-crystal X-ray study

T= 100 K

Mean(C–C) = 0.002 A˚

Rfactor = 0.032

wRfactor = 0.085

Data-to-parameter ratio = 30.7

For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

Received 23 February 2006 Accepted 13 March 2006

In the title compound, C15H10BrNO3, the molecules are

arranged into infinite chains through Br O short inter-actions. The chains are stacked to form layers. These layers are interconnected by C—H O interactions. There are two molecules in the asymmetric unit.

Comment

Chalcones have been claimed to be a class of compounds that play a vital role in antitumour (Mishra et al., 2001), anti-inflammatory (Ko et al., 2003; Tuchinda et al., 2002) and antimalarial (Domı´nguez et al., 2001) activities. It has also been documented that chalcones exhibit extremely high and fast non-linearity (Fichouet al., 1988; Zhanget al., 1990; Zhao

et al., 2000) and are easy to crystallize as non-centrosymmetric structures. Another importance of this type of compounds is their high photosensitivity and thermal stability, which are used in developing various crystalline electro-optical devices (Williams et al., 1983; Chemla et al.,1987). In view of their exceptional behaviour, chalcones have been the subject of several experimental and theoretical studies, aimed mainly at determining their crystal structures (Moorthi et al., 2005; Radha Krishnaet al., 2005; Uchidaet al., 1995). In this work, we report the synthesis and crystal structure of 3-(4-bromo-phenyl)-1-(4-nitrophenyl)prop-2-en-1-one, (I).

There are two molecules in the asymmetric unit of (I). The bond parameters are comparable with those in related struc-tures (Teh et al., 2006; Nget al., 2006; Patilet al., 2006). The dihedral angle between the benzene rings is 12.83 (7) _for

molecule Aand 41.15 (7) _{for molecule} _B_{. The nitro group}

attached at C13 is twisted away from the C10–C15 benzene ring, with torsion angles O2—N1—C13—C14 =5.8 (2) and 12.2 (2)_{, and O3—N1—C13—C12 =}_{6.0 (2) and 12.9 (2)}_for

molecules A and B, repectively. The least-squares plane through the enone fragment makes dihedral angles of 16.36 (6) and 17.09 (6)with the C1–C6 and C10–C15 benzene rings for molecule A, and of 24.49 (11) and 18.56 (12) for moleculeB.

In the crystal structure of (I), the intramolecular C7— H7A O1 interaction generates anS(5) ring motif (Bernstein

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arranged into infinite chains through short Br1A O2B(1 +x, 1 +y,z) [3.0417 (14) A˚ ] interactions and also weak short Br1A O3B(x, 1 + y, z) [3.3741 (13) A˚ ] interactions. These chains are stacked to form layers which are interconnected by C—H O interactions (Table 1).

Experimental

Chalcone derivative (I) was obtained by the condensation of 4-bromobenzaldehyde (0.01 mol) and 40_{-nitroacetophenone (0.01 mol)}

in ethanol (60 ml) in the presence of NaOH (2 ml, 30%). The resulting crude solid compound was collected by filtration, dried and recrystallized from acetone. Crystals suitable for X-ray diffraction study were grown by slow evaporation of an acetone solution over a period of 7 d.

Crystal data

C15H10BrNO3

Mr= 332.15

Triclinic,P1

a= 5.9341 (1) A˚

b= 7.9193 (1) A˚

c= 27.2996 (4) A˚

= 89.938 (1)

= 85.622 (1)

= 82.357 (1)

V= 1267.75 (3) A˚3

Z= 4

Dx= 1.740 Mg m

3 MoKradiation Cell parameters from 6533

reflections

= 0.8–35.0

= 3.25 mm1

T= 100.0 (1) K Block, yellow 0.550.390.25 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

!scans

Absorption correction: multi-scan (SADABS; Bruker, 2005)

Tmin= 0.286,Tmax= 0.444 41078 measured reflections

11069 independent reflections 9020 reflections withI> 2(I)

Rint= 0.036 max= 35.0

h=9!9

k=12!12

l=44!39

Refinement

Refinement onF2

R[F2_{> 2}₍_F2_{)] = 0.033}

wR(F2_{) = 0.085}

S= 1.11 11069 reflections 361 parameters

H-atom parameters constrained

w= 1/[2₍_F

o2) + (0.0409P)2 + 0.3692P]

whereP= (Fo2+ 2Fc2)/3 (/)max= 0.002

max= 0.94 e A˚

3 min=0.57 e A˚

3

Table 1

Hydrogen-bond geometry (A˚ ,_).

D—H A D—H H A D A D—H A

C7A—H7AA O1A 0.93 2.46 2.804 (2) 102 C7B—H7BA O1B 0.93 2.49 2.812 (2) 100 C15B—H15B O1Ai 0.93 2.58 3.240 (2) 129 Symmetry code: (i)xþ2;y;zþ1.

H atoms were placed in calculated positions, with C—H distances of 0.93 A˚ . TheUiso(H) values were constrained to be 1.2Ueq(carrier)

for all H atoms.

Data collection:APEX2(Bruker, 2005); cell refinement:APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure:SHELXTL; molecular graphics:SHELXTL; software used

to prepare material for publication:SHELXTL,PARST(Nardelli, 1995) andPLATON(Spek, 2003).

The authors thank the Malaysian Government and Universiti Sains Malaysia for Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118 and USM short-term grant No. 304/PFIZIK/635028.

References

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Bruker (2005).APEX2(Version 1.27),SAINTandSADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Chemla, D. S. & Zyss, J. (1987).Nonlinear Optical Properties of Organic Molecules and Crystals, Vols. 1 and 2. London: Academic Press.

Domı´nguez, J. N., Charris, J. E., Lobo, G., de Domı´nguez, N. G., Moreno, M. M., Riggione, F., Sanchez, E., Olson, J. & Rosenthal, P. J. (2001).Eur. J. Med. Chem.36, 555–560.

Fichou, D., Watanabe, T., Tanaka, T., Miyata, S., Goto, Y. & Nakayama, M. (1988).Jpn J. Appl. Phys.27, L429–L430.

Ko, H. H., Tsao, L. T., Yu, K. L., Liu, C. T., Wang, J. P. & Lin, C. N. (2003).

Bioorg. Med. Chem.11, 105–111.

Mishra, L., Sinha, R., Itokawa, H., Bastow, K. B., Tachibana, Y., Nakanishi, Y., Kalgore, N. & Lee, K. H. (2001).Bioorg. Med. Chem.9, 1667–1671.

organic papers

Acta Cryst.(2006). E62, o1466–o1468 Rosliet al. _C

[image:2.610.314.563.71.149.2] [image:2.610.317.563.205.459.2]

15H10BrNO3

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Figure 1

The asymmetric unit of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Dashed lines indicate hydrogen bonds.

Figure 2

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Moorthi, S. S., Chinnakali, K., Nanjundan, S., Unnithan, C. S., Fun, H.-K. & Yu, X.-L. (2005).Acta Cryst.E61, o483–485.

Nardelli, M. (1995).J. Appl. Cryst.28, 659.

Ng, S. L., Patil, P. S., Razak, I. A., Fun, H.-K. & Dharmaprakash, S. M. (2006).

Acta Cryst.E62, o893–o895.

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

Radha Krishna, J., Kumar, N. J., Krishnaiah, M., Rao, C. V., Rao, Y. K. & Puranik, V. G. (2005).Acta Cryst.E61, o1323–o1325.

Sheldrick, G. M. (1998).SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA.

Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.

Teh, J. B.-J., Patil, P. S., Fun, H.-K., Razak, I. A., & Dharmaprakash, S. M. (2006).Acta Cryst.E62, o890–o892.

Tuchinda, P., Reutrakul, V., Claeson, P., Pongprayoon, U., Sematong, T., Santisuk, T. & Taylor, W. C. (2002).Phytochemistry,59, 169–173. Uchida, T., Kozawa, K., Kimura, Y. & Goto, Y. (1995).Synth. Met.71, 1705–

1706.

Williams, D. (1983). Editor. Nonlinear Optical Properties of Organic and Polymeric Materials. Washington, DC: American Chemical Society. Zhang, G., Kinoshita, T., Sasaki, K., Goto, Y. & Nakayama, M. (1990).J. Cryst.

Growth,100, 411–416.

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organic papers

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Rosliet al. _C

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supporting information

sup-1 Acta Cryst. (2006). E62, o1466–o1468

supporting information

Acta Cryst. (2006). E62, o1466–o1468 [https://doi.org/10.1107/S1600536806009263]

3-(4-Bromophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Mohd Mustaqim Rosli, P. S. Patil, Hoong-Kun Fun, Ibrahim Abdul Razak and S. M.

Dharmaprakash

3-(4-bromophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Crystal data

C15H10BrNO3

Mr = 332.15 Triclinic, P1 Hall symbol: -P 1

a = 5.9341 (1) Å

b = 7.9193 (1) Å

c = 27.2996 (4) Å

α = 89.938 (1)°

β = 85.622 (1)°

γ = 82.357 (1)°

V = 1267.75 (3) Å3

Z = 4

F(000) = 664

Dx = 1.740 Mg m−3

Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6533 reflections

θ = 0.8–35.0°

µ = 3.25 mm−1

T = 100 K Block, yellow

0.55 × 0.39 × 0.25 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer

Radiation source: fine-focus sealed tube Graphite monochromator

Detector resolution: 8.33 pixels mm-1

ω scans

Absorption correction: multi-scan (SADABS; Bruker, 2005)

Tmin = 0.286, Tmax = 0.444

41078 measured reflections 11069 independent reflections 9020 reflections with I > 2σ(I)

Rint = 0.036

θmax = 35.0°, θmin = 0.8°

h = −9→9

k = −12→12

l = −44→39

Refinement

Refinement on F2 Least-squares matrix: full

R[F2_{> 2}_σ₍_F2_{)] = 0.033}

wR(F2_{) = 0.085}

S = 1.11

11069 reflections 361 parameters 0 restraints

Primary atom site location: structure-invariant direct methods

Secondary atom site location: difference Fourier map

Hydrogen site location: inferred from neighbouring sites

H-atom parameters constrained

w = 1/[σ2₍_F

o2) + (0.0409P)2 + 0.3692P] where P = (Fo2 + 2Fc2)/3

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supporting information

Special details

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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₎

x y z Uiso*/Ueq

Br1A 0.11160 (3) 0.65694 (2) 0.548170 (5) 0.01771 (4)

O1A 1.0276 (2) 0.15693 (16) 0.76642 (4) 0.0191 (2)

O2A 0.3440 (2) −0.10525 (17) 0.97481 (5) 0.0239 (2)

O3A 0.6758 (3) −0.25926 (17) 0.97398 (5) 0.0265 (3)

N1A 0.5394 (3) −0.14924 (17) 0.95686 (5) 0.0172 (2)

C1A 0.3362 (3) 0.43903 (19) 0.67693 (5) 0.0154 (2)

H1AA 0.2721 0.4185 0.7082 0.019*

C2A 0.2009 (3) 0.5226 (2) 0.64287 (6) 0.0164 (3)

H2AA 0.0478 0.5604 0.6514 0.020*

C3A 0.2961 (3) 0.54974 (19) 0.59563 (5) 0.0152 (2)

C4A 0.5262 (3) 0.4973 (2) 0.58252 (6) 0.0166 (3)

H4AA 0.5888 0.5163 0.5511 0.020*

C5A 0.6605 (3) 0.4160 (2) 0.61741 (6) 0.0172 (3)

H5AA 0.8145 0.3814 0.6090 0.021*

C6A 0.5687 (3) 0.38498 (18) 0.66497 (5) 0.0144 (2)

C7A 0.7172 (3) 0.30142 (19) 0.70069 (5) 0.0156 (3)

H7AA 0.8734 0.2927 0.6926 0.019*

C8A 0.6514 (3) 0.2364 (2) 0.74378 (5) 0.0158 (3)

H8AA 0.4968 0.2407 0.7533 0.019*

C9A 0.8223 (3) 0.15767 (18) 0.77650 (5) 0.0145 (2)

C10A 0.7411 (3) 0.07864 (18) 0.82339 (5) 0.0133 (2)

C11A 0.9000 (3) −0.03066 (19) 0.84773 (6) 0.0157 (3)

H11A 1.0497 −0.0532 0.8342 0.019*

C12A 0.8374 (3) −0.10573 (19) 0.89164 (6) 0.0163 (3)

H12A 0.9423 −0.1794 0.9077 0.020*

C13A 0.6126 (3) −0.06743 (18) 0.91099 (5) 0.0144 (2)

C14A 0.4509 (3) 0.04243 (19) 0.88839 (6) 0.0156 (3)

H14A 0.3027 0.0673 0.9026 0.019*

C15A 0.5160 (3) 0.11443 (19) 0.84392 (5) 0.0152 (2)

H15A 0.4098 0.1866 0.8277 0.018*

Br1B 1.11967 (3) 0.685636 (19) 0.050725 (5) 0.01636 (4)

O1B 0.2120 (2) 0.21630 (17) 0.27257 (4) 0.0216 (2)

O2B 0.8959 (2) −0.1711 (2) 0.46025 (5) 0.0304 (3)

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supporting information

C1B 0.8806 (3) 0.46306 (19) 0.17840 (5) 0.0142 (2)

H1BA 0.9290 0.4440 0.2098 0.017*

C2B 1.0106 (3) 0.54556 (18) 0.14408 (5) 0.0144 (2)

H2BA 1.1438 0.5839 0.1527 0.017*

C3B 0.9415 (3) 0.57110 (17) 0.09664 (5) 0.0136 (2)

C4B 0.7405 (3) 0.51793 (18) 0.08327 (5) 0.0142 (2)

H4BA 0.6948 0.5351 0.0516 0.017*

C5B 0.6092 (3) 0.43819 (18) 0.11848 (5) 0.0136 (2)

H5BA 0.4731 0.4040 0.1101 0.016*

C6B 0.6765 (2) 0.40813 (17) 0.16614 (5) 0.0126 (2)

C7B 0.5286 (3) 0.32658 (18) 0.20179 (5) 0.0143 (2)

H7BA 0.3813 0.3184 0.1935 0.017*

C8B 0.5869 (3) 0.26277 (19) 0.24523 (5) 0.0143 (2)

H8BA 0.7365 0.2587 0.2536 0.017*

C9B 0.4149 (3) 0.19877 (19) 0.28002 (5) 0.0145 (2)

C10B 0.4942 (3) 0.11280 (18) 0.32567 (5) 0.0132 (2)

C11B 0.3317 (3) 0.0978 (2) 0.36500 (6) 0.0162 (3)

H11B 0.1806 0.1439 0.3624 0.019*

C12B 0.3931 (3) 0.0152 (2) 0.40772 (6) 0.0172 (3)

H12B 0.2854 0.0046 0.4337 0.021*

C13B 0.6196 (3) −0.05111 (19) 0.41051 (5) 0.0147 (2)

C14B 0.7850 (3) −0.0376 (2) 0.37247 (6) 0.0171 (3)

H14B 0.9361 −0.0831 0.3754 0.021*

C15B 0.7204 (3) 0.0452 (2) 0.32999 (6) 0.0168 (3)

H15B 0.8291 0.0556 0.3042 0.020*

O3B 0.5423 (2) −0.17919 (17) 0.48512 (5) 0.0235 (2)

Atomic displacement parameters (Å2₎

U11 _U22 _U33 _U12 _U13 _U23

Br1A 0.01561 (7) 0.02389 (7) 0.01348 (7) −0.00129 (5) −0.00246 (5) 0.00455 (5)

O1A 0.0150 (5) 0.0259 (5) 0.0163 (5) −0.0027 (4) 0.0002 (4) 0.0027 (4)

O2A 0.0240 (6) 0.0279 (6) 0.0195 (6) −0.0058 (5) 0.0037 (5) 0.0049 (4)

O3A 0.0351 (7) 0.0239 (6) 0.0190 (6) 0.0020 (5) −0.0025 (5) 0.0084 (4)

N1A 0.0231 (7) 0.0157 (5) 0.0135 (6) −0.0045 (5) −0.0015 (5) 0.0013 (4)

C1A 0.0154 (6) 0.0190 (6) 0.0118 (6) −0.0023 (5) 0.0002 (5) 0.0015 (5)

C2A 0.0140 (6) 0.0210 (6) 0.0139 (6) −0.0010 (5) −0.0001 (5) 0.0023 (5)

C3A 0.0154 (6) 0.0175 (6) 0.0132 (6) −0.0022 (5) −0.0033 (5) 0.0021 (5)

C4A 0.0152 (6) 0.0209 (6) 0.0137 (6) −0.0033 (5) 0.0003 (5) 0.0016 (5)

C5A 0.0151 (7) 0.0212 (6) 0.0151 (6) −0.0021 (5) 0.0006 (5) 0.0032 (5)

C6A 0.0160 (6) 0.0163 (6) 0.0115 (6) −0.0035 (5) −0.0014 (5) 0.0017 (4)

C7A 0.0155 (6) 0.0187 (6) 0.0128 (6) −0.0024 (5) −0.0020 (5) 0.0024 (5)

C8A 0.0137 (6) 0.0208 (6) 0.0127 (6) −0.0014 (5) −0.0020 (5) 0.0030 (5)

C9A 0.0159 (6) 0.0154 (6) 0.0120 (6) −0.0016 (5) −0.0009 (5) 0.0002 (4)

C10A 0.0133 (6) 0.0149 (5) 0.0116 (6) −0.0016 (5) −0.0013 (5) 0.0005 (4)

C11A 0.0142 (6) 0.0170 (6) 0.0154 (6) 0.0002 (5) −0.0016 (5) 0.0013 (5)

C12A 0.0165 (7) 0.0166 (6) 0.0157 (6) −0.0006 (5) −0.0030 (5) 0.0029 (5)

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supporting information

C14A 0.0144 (6) 0.0165 (6) 0.0152 (6) −0.0008 (5) 0.0003 (5) 0.0019 (5)

C15A 0.0139 (6) 0.0176 (6) 0.0133 (6) 0.0003 (5) −0.0008 (5) 0.0035 (5)

Br1B 0.01656 (7) 0.01795 (7) 0.01456 (7) −0.00455 (5) 0.00272 (5) 0.00316 (5)

O1B 0.0137 (5) 0.0341 (6) 0.0174 (5) −0.0043 (5) −0.0020 (4) 0.0077 (4)

O2B 0.0202 (6) 0.0468 (8) 0.0236 (6) 0.0003 (6) −0.0059 (5) 0.0158 (6)

N1B 0.0213 (6) 0.0184 (6) 0.0140 (6) −0.0021 (5) −0.0021 (5) 0.0031 (4)

C1B 0.0134 (6) 0.0181 (6) 0.0110 (6) −0.0019 (5) −0.0012 (5) 0.0019 (4)

C2B 0.0129 (6) 0.0164 (6) 0.0143 (6) −0.0035 (5) −0.0003 (5) 0.0004 (5)

C3B 0.0145 (6) 0.0124 (5) 0.0135 (6) −0.0012 (5) 0.0018 (5) 0.0014 (4)

C4B 0.0146 (6) 0.0171 (6) 0.0109 (6) −0.0022 (5) −0.0007 (5) 0.0013 (4)

C5B 0.0132 (6) 0.0156 (6) 0.0122 (6) −0.0020 (5) −0.0015 (5) 0.0017 (4)

C6B 0.0124 (6) 0.0136 (5) 0.0117 (6) −0.0014 (4) −0.0001 (4) 0.0016 (4)

C7B 0.0131 (6) 0.0167 (6) 0.0132 (6) −0.0027 (5) −0.0004 (5) 0.0025 (4)

C8B 0.0124 (6) 0.0174 (6) 0.0130 (6) −0.0030 (5) 0.0004 (5) 0.0020 (5)

C9B 0.0146 (6) 0.0180 (6) 0.0111 (6) −0.0029 (5) −0.0005 (5) 0.0025 (4)

C10B 0.0132 (6) 0.0163 (6) 0.0101 (6) −0.0028 (5) −0.0003 (4) 0.0016 (4)

C11B 0.0119 (6) 0.0232 (7) 0.0133 (6) −0.0020 (5) 0.0004 (5) 0.0033 (5)

C12B 0.0149 (6) 0.0241 (7) 0.0122 (6) −0.0028 (5) 0.0014 (5) 0.0034 (5)

C13B 0.0162 (6) 0.0173 (6) 0.0108 (6) −0.0028 (5) −0.0025 (5) 0.0026 (4)

C14B 0.0130 (6) 0.0219 (7) 0.0157 (6) −0.0005 (5) 0.0004 (5) 0.0032 (5)

C15B 0.0145 (6) 0.0220 (7) 0.0131 (6) −0.0007 (5) 0.0013 (5) 0.0038 (5)

O3B 0.0262 (6) 0.0296 (6) 0.0149 (5) −0.0061 (5) 0.0014 (5) 0.0070 (4)

Geometric parameters (Å, º)

Br1A—C3A 1.8880 (15) Br1B—C3B 1.8874 (14)

O1A—C9A 1.2278 (19) O1B—C9B 1.2264 (19)

O2A—N1A 1.2294 (19) O2B—N1B 1.226 (2)

O3A—N1A 1.2256 (19) N1B—O3B 1.2278 (18)

N1A—C13A 1.472 (2) N1B—C13B 1.469 (2)

C1A—C2A 1.385 (2) C1B—C2B 1.386 (2)

C1A—C6A 1.402 (2) C1B—C6B 1.404 (2)

C1A—H1AA 0.9300 C1B—H1BA 0.9300

C2A—C3A 1.396 (2) C2B—C3B 1.395 (2)

C2A—H2AA 0.9300 C2B—H2BA 0.9300

C3A—C4A 1.393 (2) C3B—C4B 1.390 (2)

C4A—C5A 1.391 (2) C4B—C5B 1.395 (2)

C4A—H4AA 0.9300 C4B—H4BA 0.9300

C5A—C6A 1.404 (2) C5B—C6B 1.401 (2)

C5A—H5AA 0.9300 C5B—H5BA 0.9300

C6A—C7A 1.463 (2) C6B—C7B 1.467 (2)

C7A—C8A 1.336 (2) C7B—C8B 1.340 (2)

C7A—H7AA 0.9300 C7B—H7BA 0.9300

C8A—C9A 1.478 (2) C8B—C9B 1.479 (2)

C8A—H8AA 0.9300 C8B—H8BA 0.9300

C9A—C10A 1.499 (2) C9B—C10B 1.497 (2)

C10A—C11A 1.399 (2) C10B—C15B 1.391 (2)

(8)

supporting information

C11A—C12A 1.385 (2) C11B—C12B 1.386 (2)

C11A—H11A 0.9300 C11B—H11B 0.9300

C12A—C13A 1.391 (2) C12B—C13B 1.384 (2)

C12A—H12A 0.9300 C12B—H12B 0.9300

C13A—C14A 1.388 (2) C13B—C14B 1.387 (2)

C14A—C15A 1.391 (2) C14B—C15B 1.386 (2)

C14A—H14A 0.9300 C14B—H14B 0.9300

C15A—H15A 0.9300 C15B—H15B 0.9300

O3A—N1A—O2A 124.46 (14) O2B—N1B—O3B 123.86 (14)

O3A—N1A—C13A 117.71 (14) O2B—N1B—C13B 118.08 (13)

O2A—N1A—C13A 117.81 (14) O3B—N1B—C13B 118.06 (14)

C2A—C1A—C6A 120.90 (14) C2B—C1B—C6B 120.49 (13)

C2A—C1A—H1AA 119.6 C2B—C1B—H1BA 119.8

C6A—C1A—H1AA 119.6 C6B—C1B—H1BA 119.8

C1A—C2A—C3A 119.51 (15) C1B—C2B—C3B 119.99 (13)

C1A—C2A—H2AA 120.2 C1B—C2B—H2BA 120.0

C3A—C2A—H2AA 120.2 C3B—C2B—H2BA 120.0

C4A—C3A—C2A 121.02 (14) C4B—C3B—C2B 120.95 (13)

C4A—C3A—Br1A 118.97 (11) C4B—C3B—Br1B 119.79 (11)

C2A—C3A—Br1A 120.01 (12) C2B—C3B—Br1B 119.23 (11)

C5A—C4A—C3A 118.73 (14) C3B—C4B—C5B 118.41 (13)

C5A—C4A—H4AA 120.6 C3B—C4B—H4BA 120.8

C3A—C4A—H4AA 120.6 C5B—C4B—H4BA 120.8

C4A—C5A—C6A 121.47 (15) C4B—C5B—C6B 121.86 (13)

C4A—C5A—H5AA 119.3 C4B—C5B—H5BA 119.1

C6A—C5A—H5AA 119.3 C6B—C5B—H5BA 119.1

C1A—C6A—C5A 118.35 (14) C5B—C6B—C1B 118.27 (13)

C1A—C6A—C7A 122.07 (13) C5B—C6B—C7B 119.24 (13)

C5A—C6A—C7A 119.56 (14) C1B—C6B—C7B 122.46 (13)

C8A—C7A—C6A 126.65 (15) C8B—C7B—C6B 125.83 (14)

C8A—C7A—H7AA 116.7 C8B—C7B—H7BA 117.1

C6A—C7A—H7AA 116.7 C6B—C7B—H7BA 117.1

C7A—C8A—C9A 120.50 (14) C7B—C8B—C9B 120.52 (14)

C7A—C8A—H8AA 119.8 C7B—C8B—H8BA 119.7

C9A—C8A—H8AA 119.8 C9B—C8B—H8BA 119.7

O1A—C9A—C8A 121.71 (14) O1B—C9B—C8B 121.81 (14)

O1A—C9A—C10A 119.55 (14) O1B—C9B—C10B 120.01 (13)

C8A—C9A—C10A 118.74 (13) C8B—C9B—C10B 118.17 (13)

C11A—C10A—C15A 119.68 (14) C15B—C10B—C11B 119.32 (14)

C11A—C10A—C9A 117.90 (13) C15B—C10B—C9B 122.50 (13)

C15A—C10A—C9A 122.40 (13) C11B—C10B—C9B 118.17 (14)

C12A—C11A—C10A 120.91 (14) C12B—C11B—C10B 120.94 (15)

C12A—C11A—H11A 119.5 C12B—C11B—H11B 119.5

C10A—C11A—H11A 119.5 C10B—C11B—H11B 119.5

C11A—C12A—C13A 117.91 (14) C13B—C12B—C11B 118.01 (14)

C11A—C12A—H12A 121.0 C13B—C12B—H12B 121.0

(9)

supporting information

C14A—C13A—C12A 122.94 (14) C12B—C13B—C14B 122.57 (14)

C14A—C13A—N1A 117.92 (14) C12B—C13B—N1B 119.56 (13)

C12A—C13A—N1A 119.13 (14) C14B—C13B—N1B 117.87 (14)

C13A—C14A—C15A 118.31 (14) C15B—C14B—C13B 118.62 (15)

C13A—C14A—H14A 120.8 C15B—C14B—H14B 120.7

C15A—C14A—H14A 120.8 C13B—C14B—H14B 120.7

C14A—C15A—C10A 120.24 (14) C14B—C15B—C10B 120.53 (14)

C14A—C15A—H15A 119.9 C14B—C15B—H15B 119.7

C10A—C15A—H15A 119.9 C10B—C15B—H15B 119.7

C6A—C1A—C2A—C3A 1.6 (2) C6B—C1B—C2B—C3B −1.5 (2)

C1A—C2A—C3A—C4A −1.4 (2) C1B—C2B—C3B—C4B 1.3 (2)

C1A—C2A—C3A—Br1A 177.96 (11) C1B—C2B—C3B—Br1B 179.41 (11)

C2A—C3A—C4A—C5A 0.4 (2) C2B—C3B—C4B—C5B 0.0 (2)

Br1A—C3A—C4A—C5A −178.99 (11) Br1B—C3B—C4B—C5B −178.10 (11)

C4A—C5A—C6A—C7A −179.03 (14) C2B—C1B—C6B—C7B −177.45 (14)

C7A—C8A—C9A—O1A 3.6 (2) C7B—C8B—C9B—O1B −7.0 (2)

O1A—C9A—C10A—C11A −16.1 (2) O1B—C9B—C10B—C15B 160.90 (15)

O1A—C9A—C10A—C15A 161.97 (14) O1B—C9B—C10B—C11B −17.9 (2)

C11A—C12A—C13A—N1A 178.22 (13) C11B—C12B—C13B—N1B −179.95 (14)

O3A—N1A—C13A—C14A 172.60 (14) O2B—N1B—C13B—C12B −167.72 (15)

O2A—N1A—C13A—C14A −5.8 (2) O3B—N1B—C13B—C12B 12.9 (2)

O3A—N1A—C13A—C12A −6.0 (2) O2B—N1B—C13B—C14B 12.2 (2)

O2A—N1A—C13A—C12A 175.54 (14) O3B—N1B—C13B—C14B −167.09 (14)

N1A—C13A—C14A—C15A −177.21 (13) N1B—C13B—C14B—C15B 179.83 (14)

Hydrogen-bond geometry (Å, º)

D—H···A D—H H···A D···A D—H···A

(10)

supporting information

C7B—H7BA···O1B 0.93 2.49 2.812 (2) 100

C15B—H15B···O1Ai _0.93 _2.58 _{3.240 (2)} ₁₂₉

3 (4 Bromo­phen­yl) 1 (4 nitro­phen­yl)prop 2 en 1 one

organic papers

o1466

3-(4-Bromophenyl)-1-(4-nitrophenyl)-prop-2-en-1-one

organic papers

o1467

organic papers

o1468

supporting information

supporting information

3-(4-Bromophenyl)-1-(4-nitrophenyl)prop-2-en-1-one

Mohd Mustaqim Rosli, P. S. Patil, Hoong-Kun Fun, Ibrahim Abdul Razak and S. M.

Dharmaprakash

supporting information

supporting information

supporting information

supporting information

supporting information

supporting information

3 (4 Bromophenyl) 1 (4 nitrophenyl)prop 2 en 1 one