(2E)-1-(3-Bromo­phen­yl)-3-(6-meth­oxy-2-naphth­yl)prop-2-en-1-one

Harrison, W.T.A.; Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536810035117

(2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one

W. T. A. Harrison, A. N. Mayekar, H. S. Yathirajan and B. Narayana

In the title compound, C₂₀H₁₅BrO₂, the prop-2-en-1-one fragment is substantially twisted [C—C—C—O = 23.0 (11)°]. The dihedral angle between the benzene and naphthalene rings is 44.28 (13)°. The only possible directional interactions in the crystal are weak C—H

π contacts, which generate (001) sheets.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810035117/tk2699sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810035117/tk2699Isup2.hkl Contains datablock I

CCDC reference: 797759

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.010 Å
R factor = 0.082
wR factor = 0.163
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level B
RINTA01_ALERT_3_B  The value of Rint is greater than 0.18
            Rint given   0.228
PLAT020_ALERT_3_B The value of Rint is greater than 0.12 .........       0.23

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds (x 1000) Ang ..         10
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         14

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.      12.29

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, (I), (Fig. 1), was prepared as part of our ongoing studies (Yathirajan et al., 2007a,b; Jasinski et al., 2009) of substituted phenyl/naphthyl chalcone derivatives as possible candidates for non-linear optical materials (Sarojini et al., 2006). However, (I) crystallizes in a centrosymmetric space group, thus its second-harmonic generation (SHG) response must be zero.

The prop-2-en-1-one (enone) fragment in (I) is substantially twisted, as indicated by the C11—C12—C13—O2 torsion angle of 23.0 (11)°. The dihedral angle between the aromatic ring systems is 44.28 (13)°. Equivalent data for related structures are as follows: (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Yathirajan et al., 2007a): -10.9 (2) and 44.94 (4)°; (2E)-3-(6-methoxy-2-naphthyl)-1-phenylprop-2-en-1-one (Yathirajan et al., 2007b): -15.9 (4) and 14.9 (8)°; (2E)-1-(2-hydroxyphenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Jasinski et al., 2009): -14.9 (2) and 31.7 (3)°. Otherwise, the bond lengths for (I) fall within their expected ranges (Allen et al., 1987).

In the crystal of (I), the only possible directional interactions between molecules are weak C—H···π contacts in which the C3–C8 ring of the naphthyl moiety provides both the C—H donor groups and the aromatic acceptor surface (Table 1, Fig. 2). Together, these generate (001) sheets.

Related literature top

For related structures, see: Yathirajan et al. (2007a,b); Jasinski et al. (2009). For background to the non-linear optical properties of chalcones, see: Sarojini et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

To a thoroughly stirred solution of 6-methoxy-2-naphthaldehyde (1.86 g, 0.01 mol) and 3-bromoacetophenone (1.99 g, 0.01 mol) in 25 ml methanol, 5 ml of 40% KOH solution was added. The reaction mixture was stirred overnight and the solid separated was collected by filtration. The product obtained was recrystallized from methanol. Colourless slabs of (I) were grown by the slow evaporation of the ethylacetate solution (m.p. 427–429 K).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).
	Fig. 2. Partial packing diagram for (I) showing the possible weak C—H···π contacts. All H atoms except H4 and H7 omitted for clarity. Symmetry codes: (i) 1/2–x, y–1/2, z; (ii) 1–x, 1/2 + y, 1/2–z.

(2E)-1-(3-Bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one top

Crystal data top

C₂₀H₁₅BrO₂	F(000) = 1488
M_r = 367.23	D_x = 1.563 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 55128 reflections
a = 14.0955 (14) Å	θ = 2.9–27.5°
b = 6.1295 (6) Å	µ = 2.64 mm⁻¹
c = 36.119 (4) Å	T = 120 K
V = 3120.6 (5) Å³	Slab, colourless
Z = 8	0.11 × 0.09 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	3545 independent reflections
Radiation source: fine-focus sealed tube	1719 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.228
ω and ϕ scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −18→18
T_min = 0.760, T_max = 0.925	k = −7→7
28579 measured reflections	l = −46→46

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
3545 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

C₂₀H₁₅BrO₂	V = 3120.6 (5) Å³
M_r = 367.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.0955 (14) Å	µ = 2.64 mm⁻¹
b = 6.1295 (6) Å	T = 120 K
c = 36.119 (4) Å	0.11 × 0.09 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	3545 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1719 reflections with I > 2σ(I)
T_min = 0.760, T_max = 0.925	R_int = 0.228
28579 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
3545 reflections	Δρ_max = 0.61 e Å⁻³
209 parameters	Δρ_min = −0.63 e Å⁻³

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

	x	y	z	U_iso*/U_eq
C1	0.3881 (4)	0.3963 (12)	0.14070 (18)	0.0269 (16)
C2	0.3536 (5)	0.2944 (11)	0.17160 (18)	0.0260 (16)
H2	0.3224	0.1576	0.1695	0.031*
C3	0.3647 (4)	0.3940 (11)	0.20683 (18)	0.0244 (15)
C4	0.3332 (4)	0.2939 (11)	0.23966 (18)	0.0247 (16)
H4	0.3057	0.1526	0.2384	0.030*
C5	0.3411 (4)	0.3933 (11)	0.27329 (17)	0.0257 (15)
H5	0.3192	0.3202	0.2949	0.031*
C6	0.3820 (4)	0.6074 (12)	0.27654 (18)	0.0226 (15)
C7	0.4144 (4)	0.7064 (11)	0.24441 (19)	0.0266 (17)
H7	0.4418	0.8477	0.2460	0.032*
C8	0.4083 (4)	0.6051 (12)	0.20954 (18)	0.0249 (16)
C9	0.4425 (5)	0.7045 (12)	0.1768 (2)	0.0316 (18)
H9	0.4724	0.8432	0.1782	0.038*
C10	0.4332 (4)	0.6034 (12)	0.14329 (19)	0.0290 (16)
H10	0.4569	0.6718	0.1216	0.035*
C11	0.3820 (4)	0.7262 (12)	0.31156 (18)	0.0262 (18)
H11	0.4035	0.8730	0.3107	0.031*
C12	0.3550 (5)	0.6518 (11)	0.34459 (18)	0.0290 (17)
H12	0.3356	0.5039	0.3468	0.035*
C13	0.3544 (5)	0.7926 (12)	0.3780 (2)	0.0305 (17)
C14	0.3642 (4)	0.6878 (12)	0.4150 (2)	0.0276 (17)
C15	0.3486 (5)	0.8158 (12)	0.44671 (19)	0.0312 (17)
H15	0.3274	0.9622	0.4442	0.037*
C16	0.3638 (5)	0.7308 (12)	0.4810 (2)	0.0313 (17)
C17	0.3927 (5)	0.5156 (12)	0.48559 (19)	0.0290 (18)
H17	0.4014	0.4555	0.5096	0.035*
C18	0.4085 (5)	0.3918 (13)	0.4543 (2)	0.0363 (18)
H18	0.4305	0.2461	0.4571	0.044*
C19	0.3934 (5)	0.4728 (12)	0.4191 (2)	0.035 (2)
H19	0.4029	0.3827	0.3981	0.042*
C20	0.3351 (5)	0.1184 (12)	0.10028 (19)	0.0400 (19)
H20A	0.3318	0.0822	0.0739	0.060*
H20B	0.2707	0.1298	0.1103	0.060*
H20C	0.3697	0.0036	0.1135	0.060*
O1	0.3827 (3)	0.3202 (8)	0.10487 (13)	0.0351 (13)
O2	0.3495 (4)	0.9934 (9)	0.37483 (13)	0.0361 (12)
Br1	0.34948 (6)	0.90763 (13)	0.52413 (2)	0.0403 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.024 (4)	0.033 (4)	0.024 (4)	0.007 (4)	−0.003 (3)	−0.002 (4)
C2	0.027 (4)	0.023 (4)	0.027 (4)	−0.005 (4)	−0.011 (4)	−0.001 (3)
C3	0.022 (4)	0.022 (4)	0.029 (4)	0.002 (4)	0.000 (3)	−0.003 (4)
C4	0.021 (4)	0.019 (4)	0.034 (4)	0.002 (3)	0.004 (3)	0.006 (3)
C5	0.022 (3)	0.031 (4)	0.024 (4)	−0.002 (4)	0.003 (3)	0.008 (4)
C6	0.014 (3)	0.023 (4)	0.030 (4)	−0.001 (3)	−0.002 (3)	−0.001 (4)
C7	0.013 (3)	0.029 (4)	0.038 (5)	−0.001 (3)	0.002 (3)	0.004 (4)
C8	0.018 (3)	0.031 (4)	0.026 (4)	0.005 (4)	−0.001 (3)	0.000 (4)
C9	0.027 (4)	0.034 (4)	0.034 (5)	0.002 (4)	0.003 (4)	0.003 (4)
C10	0.022 (4)	0.032 (4)	0.033 (4)	0.000 (4)	0.003 (3)	0.009 (4)
C11	0.019 (4)	0.028 (4)	0.031 (4)	0.001 (3)	0.000 (3)	−0.009 (4)
C12	0.024 (4)	0.031 (4)	0.032 (4)	−0.006 (4)	0.000 (4)	−0.009 (3)
C13	0.021 (4)	0.032 (5)	0.038 (4)	−0.001 (4)	0.011 (4)	−0.001 (4)
C14	0.016 (4)	0.033 (4)	0.034 (4)	−0.002 (3)	0.002 (3)	−0.004 (4)
C15	0.025 (4)	0.030 (4)	0.039 (4)	−0.004 (4)	0.002 (4)	−0.007 (4)
C16	0.028 (4)	0.034 (4)	0.032 (4)	0.003 (3)	0.003 (4)	−0.004 (4)
C17	0.027 (4)	0.034 (4)	0.026 (4)	−0.003 (3)	−0.001 (3)	0.002 (3)
C18	0.030 (4)	0.038 (5)	0.041 (5)	0.000 (4)	−0.005 (4)	−0.003 (5)
C19	0.023 (4)	0.040 (5)	0.042 (5)	−0.001 (3)	−0.011 (4)	−0.007 (4)
C20	0.059 (5)	0.033 (4)	0.029 (4)	−0.007 (4)	−0.005 (4)	−0.004 (4)
O1	0.045 (3)	0.035 (3)	0.026 (3)	−0.002 (2)	0.001 (2)	−0.001 (3)
O2	0.034 (3)	0.044 (3)	0.031 (3)	0.006 (3)	0.001 (3)	−0.002 (3)
Br1	0.0471 (4)	0.0440 (5)	0.0298 (4)	0.0048 (5)	0.0016 (4)	−0.0062 (4)

Geometric parameters (Å, º) top

C1—C2	1.369 (9)	C11—H11	0.9500
C1—O1	1.378 (8)	C12—C13	1.483 (9)
C1—C10	1.422 (9)	C12—H12	0.9500
C2—C3	1.420 (9)	C13—O2	1.238 (8)
C2—H2	0.9500	C13—C14	1.489 (10)
C3—C4	1.407 (9)	C14—C19	1.389 (9)
C3—C8	1.436 (9)	C14—C15	1.406 (9)
C4—C5	1.364 (9)	C15—C16	1.361 (9)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.439 (9)	C16—C17	1.391 (10)
C5—H5	0.9500	C16—Br1	1.909 (7)
C6—C7	1.387 (9)	C17—C18	1.379 (9)
C6—C11	1.459 (9)	C17—H17	0.9500
C7—C8	1.407 (9)	C18—C19	1.380 (10)
C7—H7	0.9500	C18—H18	0.9500
C8—C9	1.414 (9)	C19—H19	0.9500
C9—C10	1.366 (9)	C20—O1	1.418 (8)
C9—H9	0.9500	C20—H20A	0.9800
C10—H10	0.9500	C20—H20B	0.9800
C11—C12	1.333 (9)	C20—H20C	0.9800

C2—C1—O1	126.3 (6)	C6—C11—H11	116.4
C2—C1—C10	120.8 (6)	C11—C12—C13	122.0 (7)
O1—C1—C10	112.9 (6)	C11—C12—H12	119.0
C1—C2—C3	119.7 (6)	C13—C12—H12	119.0
C1—C2—H2	120.1	O2—C13—C12	120.3 (7)
C3—C2—H2	120.1	O2—C13—C14	121.1 (7)
C4—C3—C2	122.2 (6)	C12—C13—C14	118.6 (6)
C4—C3—C8	118.1 (6)	C19—C14—C15	119.2 (7)
C2—C3—C8	119.7 (6)	C19—C14—C13	122.2 (7)
C5—C4—C3	122.0 (6)	C15—C14—C13	118.5 (6)
C5—C4—H4	119.0	C16—C15—C14	120.2 (7)
C3—C4—H4	119.0	C16—C15—H15	119.9
C4—C5—C6	120.9 (6)	C14—C15—H15	119.9
C4—C5—H5	119.6	C15—C16—C17	121.2 (7)
C6—C5—H5	119.6	C15—C16—Br1	120.6 (5)
C7—C6—C5	117.6 (6)	C17—C16—Br1	118.2 (5)
C7—C6—C11	120.5 (6)	C18—C17—C16	118.1 (7)
C5—C6—C11	121.7 (6)	C18—C17—H17	120.9
C6—C7—C8	122.4 (6)	C16—C17—H17	120.9
C6—C7—H7	118.8	C17—C18—C19	122.1 (7)
C8—C7—H7	118.8	C17—C18—H18	119.0
C7—C8—C9	122.5 (7)	C19—C18—H18	119.0
C7—C8—C3	119.0 (6)	C18—C19—C14	119.1 (8)
C9—C8—C3	118.5 (6)	C18—C19—H19	120.4
C10—C9—C8	120.8 (7)	C14—C19—H19	120.4
C10—C9—H9	119.6	O1—C20—H20A	109.5
C8—C9—H9	119.6	O1—C20—H20B	109.5
C9—C10—C1	120.4 (7)	H20A—C20—H20B	109.5
C9—C10—H10	119.8	O1—C20—H20C	109.5
C1—C10—H10	119.8	H20A—C20—H20C	109.5
C12—C11—C6	127.2 (7)	H20B—C20—H20C	109.5
C12—C11—H11	116.4	C1—O1—C20	115.6 (6)

O1—C1—C2—C3	−180.0 (6)	C7—C6—C11—C12	−178.5 (7)
C10—C1—C2—C3	−1.4 (9)	C5—C6—C11—C12	7.2 (10)
C1—C2—C3—C4	−178.0 (6)	C6—C11—C12—C13	−177.3 (6)
C1—C2—C3—C8	2.7 (9)	C11—C12—C13—O2	23.0 (11)
C2—C3—C4—C5	−177.7 (6)	C11—C12—C13—C14	−154.4 (6)
C8—C3—C4—C5	1.6 (9)	O2—C13—C14—C19	−163.5 (7)
C3—C4—C5—C6	0.2 (10)	C12—C13—C14—C19	13.8 (10)
C4—C5—C6—C7	−1.1 (9)	O2—C13—C14—C15	12.6 (10)
C4—C5—C6—C11	173.4 (6)	C12—C13—C14—C15	−170.1 (6)
C5—C6—C7—C8	0.1 (9)	C19—C14—C15—C16	1.2 (10)
C11—C6—C7—C8	−174.5 (6)	C13—C14—C15—C16	−175.0 (6)
C6—C7—C8—C9	−179.1 (6)	C14—C15—C16—C17	−1.5 (10)
C6—C7—C8—C3	1.7 (10)	C14—C15—C16—Br1	176.6 (5)
C4—C3—C8—C7	−2.5 (9)	C15—C16—C17—C18	1.9 (10)
C2—C3—C8—C7	176.8 (6)	Br1—C16—C17—C18	−176.2 (5)
C4—C3—C8—C9	178.3 (6)	C16—C17—C18—C19	−2.2 (10)
C2—C3—C8—C9	−2.4 (9)	C17—C18—C19—C14	2.0 (10)
C7—C8—C9—C10	−178.3 (6)	C15—C14—C19—C18	−1.5 (10)
C3—C8—C9—C10	0.9 (10)	C13—C14—C19—C18	174.6 (6)
C8—C9—C10—C1	0.4 (10)	C2—C1—O1—C20	1.2 (9)
C2—C1—C10—C9	−0.2 (10)	C10—C1—O1—C20	−177.5 (6)
O1—C1—C10—C9	178.6 (6)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···Cg2ⁱ	0.95	2.70	3.432 (6)	134
C7—H7···Cg2ⁱⁱ	0.95	2.80	3.520 (6)	134

Symmetry codes: (i) −x+1/2, y−3/2, z; (ii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₅BrO₂
M_r	367.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	14.0955 (14), 6.1295 (6), 36.119 (4)
V (Å³)	3120.6 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.64
Crystal size (mm)	0.11 × 0.09 × 0.03

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.760, 0.925
No. of measured, independent and observed [I > 2σ(I)] reflections	28579, 3545, 1719
R_int	0.228
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.163, 1.05
No. of reflections	3545
No. of parameters	209
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0343P)² + 12.2862P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.63

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), and SORTAV (Blessing, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).