(2E)-1-(2-Hy­droxy-5-methyl­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one

In the title compound, C₁₇H₁₆O₃, the dihedral angle between the aromatic rings is 4.59 (7)° and an intra­molecular O—H...O hydrogen bond generates an S(6) ring. In the crystal, adjacent mol­ecules are linked by C—H...O hydrogen bonds, leading to the formation of [001] supra­molecular chains. Weak C—H...π inter­actions consolidate the packing.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.047
• wR factor = 0.131
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level C
SHFSU01_ALERT_2_C  Test not performed. _refine_ls_shift/su_max and
            _refine_ls_shift/esd_max not present.
            Absolute value of the parameter shift to su ratio given   0.001
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         12
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   1 ALERT level G = General information/check it is not something unexpected

   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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

In continuation of our studies on the crystal structures of chalcones (Fun et al., 2010), we now report the synthesis and crystal structure of the title compound, (I). The structures of some related chalcones viz: (Z)-3-(9-anthryl)-1-(4-methoxyphenyl)prop-2-en-1-one (Chantrapromma et al., 2009), (Z)-3-(9-anthryl)- 1-(2-thienyl)prop-2-en-1-one (Fun et al., 2009), (E)-3- (anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one (Suwunwong et al., 2009), (Z)-3-(9-anthryl)-1-(4-bromophenyl)-2-(4-nitro-1H- imidazol-1-yl)prop-2-en-1-one (Lu et al., 2009),(Z)-3- (9-anthryl)-2-(4-nitro-1H-imidazol-1-yl)-1-p-tolylprop- 2-en-1-one (Wang et al., 2009), (E)-3-(9-anthryl)-1- (4-fluorophenyl)-2-(4-nitro-1H-imidazol-1-yl)prop-2-en-1-one (Wang et al., 2010), (E)-3-(anthracen-9-yl)-1-(furan-2-yl) prop-2-en-1-one (Horkaew et al., 2010), and an orthorhombic polymorph of (Z)-3-(9-anthryl)-1-(2-thienyl)prop-2-en-1-one (Chantrapromma et al., 2010) and 2(E)-3-(4-hydroxyphenyl)-1-(4-chlorophenyl) prop-2-en-1-one (Jasinski et al.,2011) have been reported.

The molecular structure is shown in Fig. 1. An intramolecular O1—H1O1···O2 hydrogen bond (Table 1) stabilizes the molecular structure and forms an S(6) ring motif (Bernstein et al., 1995). The dihedral angle between the phenyl (C1–C6) ring and the methoxy-substituted phenyl (C10–C15) ring is 4.59 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to the related structures (Fun et al., 2010).

In the crystal packing (Fig. 2), the molecules are linked into infinite one-dimensional chain along the c-axis by intermolecular C11—H11A···O3 hydrogen bonds (Table 1). There are also C—H···π interactions (Table 1) which involves C16 and phenyl ring (Cg1 = C1–C6).

Related literature

For a related structure and background references to chalcones, see: Fun et al. (2010). For related structures, see: Chantrapromma et al. (2009, 2010); Fun et al. (2009); Horkaew et al. (2010); Lu et al. (2009); Suwunwong et al. (2009); Wang et al. (2009, 2010); Jasinski et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

S2. Experimental

2-Hydroxy-5-methylacetophenone (1.50 g, 0.01 mol) was mixed with 4-methoxybenzaldehyde (1.36 g, 0.01 mol) and dissolved in ethanol (40 ml). To this solution, 5 ml of KOH (50%) was added at 278 K. The reaction mixture stirred for 6 h and poured on to crushed ice. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. The resulting crude yellow solid was filtered, washed successively with dilute HCl solution and distilled water and finally recrystallized from ethanol (95%) to give the pure chalcone. Orange blocks of (I) were grown by the slow evaporation of the solution of the compound in ethyl alcohol (m. p.: 361 K). Composition: Found (Calculated) for C₁₇H₁₆O₃, C: 76.10 (76.16); H: 6.01 (6.05).

S3. Refinement

H1O1 atom attached to the O atom was located from the difference map and refined freely [O–H = 0.94 (2) Å]. The remaining H atoms were positioned geometrically [C–H = 0.93 or 0.96 Å] and refined using a riding model with U_iso(H) = 1.2 or 1.5 U_eq(C). A rotating group model was applied to the methyl groups.

Computing details

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

Figures

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. The dashed line indicates the intramolecular bond.
	Fig. 2. The crystal packing of the title compound, viewed along the b axis.

(2E)-1-(2-Hydroxy-5-methylphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Crystal data

C17H16O3	F(000) = 568
Mr = 268.30	Dx = 1.256 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2769 reflections
a = 12.6990 (18) Å	θ = 2.8–28.6°
b = 8.8022 (13) Å	µ = 0.09 mm^−1
c = 13.172 (2) Å	T = 296 K
β = 105.565 (2)°	Block, orange
V = 1418.3 (4) Å^3	0.46 × 0.32 × 0.18 mm
Z = 4

Data collection

Bruker SMART APEXII DUO CCD diffractometer	4090 independent reflections
Radiation source: fine-focus sealed tube	2608 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 29.9°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→17
Tmin = 0.962, Tmax = 0.984	k = −10→12
11493 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.1652P] where P = (Fo^2 + 2Fc^2)/3
4090 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.13821 (11)	0.18686 (15)	0.32930 (8)	0.0794 (4)
O2	0.26594 (9)	0.35672 (14)	0.26545 (7)	0.0758 (3)
O3	0.51456 (8)	0.87081 (13)	−0.15126 (7)	0.0666 (3)
C1	0.03317 (10)	0.26022 (14)	0.04622 (10)	0.0486 (3)
H1A	0.0518	0.3125	−0.0078	0.058*
C2	−0.06268 (11)	0.17724 (16)	0.02260 (12)	0.0553 (3)
C3	−0.08898 (13)	0.10217 (19)	0.10552 (15)	0.0704 (4)
H3A	−0.1538	0.0472	0.0921	0.084*
C4	−0.02277 (15)	0.10664 (19)	0.20568 (15)	0.0728 (4)
H4A	−0.0427	0.0543	0.2590	0.087*
C5	0.07432 (12)	0.18853 (16)	0.22906 (11)	0.0581 (4)
C6	0.10376 (10)	0.26897 (14)	0.14840 (10)	0.0468 (3)
C7	0.20644 (11)	0.35632 (16)	0.17338 (10)	0.0502 (3)
C8	0.23943 (10)	0.44232 (15)	0.09183 (10)	0.0488 (3)
H8A	0.1929	0.4469	0.0240	0.059*
C9	0.33518 (10)	0.51410 (15)	0.11356 (10)	0.0478 (3)
H9A	0.3790	0.5037	0.1822	0.057*
C10	0.38013 (9)	0.60674 (14)	0.04375 (9)	0.0442 (3)
C11	0.48166 (10)	0.67433 (16)	0.08326 (10)	0.0501 (3)
H11A	0.5188	0.6589	0.1536	0.060*
C12	0.52938 (10)	0.76377 (16)	0.02169 (10)	0.0504 (3)
H12A	0.5973	0.8081	0.0504	0.060*
C13	0.47519 (10)	0.78657 (15)	−0.08275 (9)	0.0477 (3)
C14	0.37276 (11)	0.72165 (17)	−0.12373 (10)	0.0581 (4)
H14A	0.3355	0.7385	−0.1939	0.070*
C15	0.32612 (10)	0.63348 (16)	−0.06231 (10)	0.0542 (3)
H15A	0.2577	0.5907	−0.0912	0.065*
C16	−0.13460 (12)	0.16543 (19)	−0.08791 (14)	0.0704 (4)
H16A	−0.1021	0.2204	−0.1347	0.106*
H16B	−0.2051	0.2077	−0.0911	0.106*
H16C	−0.1427	0.0606	−0.1086	0.106*
C17	0.61893 (12)	0.93974 (19)	−0.11419 (12)	0.0645 (4)
H17A	0.6362	0.9942	−0.1708	0.097*
H17B	0.6731	0.8627	−0.0886	0.097*
H17C	0.6181	1.0090	−0.0581	0.097*
H1O1	0.2008 (17)	0.245 (2)	0.3290 (16)	0.107 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.1019 (9)	0.0879 (9)	0.0533 (6)	−0.0055 (7)	0.0295 (6)	0.0145 (6)
O2	0.0760 (7)	0.1013 (9)	0.0451 (5)	−0.0174 (6)	0.0078 (5)	0.0079 (5)
O3	0.0642 (6)	0.0840 (8)	0.0509 (5)	−0.0187 (5)	0.0142 (5)	0.0088 (5)
C1	0.0523 (7)	0.0438 (7)	0.0542 (7)	0.0022 (6)	0.0222 (6)	−0.0008 (6)
C2	0.0514 (7)	0.0456 (8)	0.0729 (9)	0.0012 (6)	0.0239 (6)	−0.0062 (6)
C3	0.0651 (9)	0.0595 (10)	0.0961 (13)	−0.0098 (7)	0.0380 (9)	−0.0011 (9)
C4	0.0863 (11)	0.0626 (10)	0.0845 (11)	−0.0079 (9)	0.0488 (10)	0.0088 (8)
C5	0.0756 (9)	0.0509 (8)	0.0567 (8)	0.0042 (7)	0.0331 (7)	0.0038 (6)
C6	0.0552 (7)	0.0413 (7)	0.0496 (7)	0.0036 (6)	0.0241 (6)	−0.0015 (5)
C7	0.0570 (7)	0.0503 (8)	0.0454 (6)	0.0025 (6)	0.0172 (6)	−0.0010 (5)
C8	0.0537 (7)	0.0499 (7)	0.0428 (6)	−0.0015 (6)	0.0130 (5)	−0.0013 (5)
C9	0.0503 (6)	0.0489 (7)	0.0435 (6)	0.0024 (6)	0.0114 (5)	−0.0028 (5)
C10	0.0445 (6)	0.0453 (7)	0.0427 (6)	0.0028 (5)	0.0113 (5)	−0.0040 (5)
C11	0.0458 (6)	0.0617 (9)	0.0395 (6)	0.0009 (6)	0.0058 (5)	0.0004 (6)
C12	0.0400 (6)	0.0621 (9)	0.0462 (6)	−0.0029 (6)	0.0065 (5)	−0.0027 (6)
C13	0.0483 (6)	0.0521 (8)	0.0434 (6)	−0.0004 (6)	0.0135 (5)	−0.0012 (5)
C14	0.0554 (7)	0.0723 (10)	0.0401 (6)	−0.0100 (7)	0.0016 (6)	0.0034 (6)
C15	0.0465 (7)	0.0632 (9)	0.0481 (7)	−0.0098 (6)	0.0042 (5)	−0.0018 (6)
C16	0.0544 (8)	0.0657 (10)	0.0876 (11)	−0.0045 (7)	0.0131 (8)	−0.0117 (8)
C17	0.0614 (8)	0.0662 (10)	0.0707 (9)	−0.0104 (7)	0.0257 (7)	−0.0025 (7)

Geometric parameters (Å, º)

O1—C5	1.3517 (18)	C9—C10	1.4554 (17)
O1—H1O1	0.94 (2)	C9—H9A	0.9300
O2—C7	1.2449 (15)	C10—C11	1.3881 (17)
O3—C13	1.3624 (15)	C10—C15	1.4011 (17)
O3—C17	1.4198 (17)	C11—C12	1.3814 (18)
C1—C2	1.3815 (18)	C11—H11A	0.9300
C1—C6	1.4048 (18)	C12—C13	1.3778 (17)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.392 (2)	C13—C14	1.3903 (18)
C2—C16	1.500 (2)	C14—C15	1.3656 (19)
C3—C4	1.361 (2)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.390 (2)	C16—H16A	0.9600
C4—H4A	0.9300	C16—H16B	0.9600
C5—C6	1.4082 (18)	C16—H16C	0.9600
C6—C7	1.4729 (18)	C17—H17A	0.9600
C7—C8	1.4641 (18)	C17—H17B	0.9600
C8—C9	1.3315 (17)	C17—H17C	0.9600
C8—H8A	0.9300
C5—O1—H1O1	106.0 (13)	C11—C10—C9	119.05 (11)
C13—O3—C17	118.65 (11)	C15—C10—C9	123.64 (11)
C2—C1—C6	122.82 (12)	C12—C11—C10	122.26 (11)
C2—C1—H1A	118.6	C12—C11—H11A	118.9
C6—C1—H1A	118.6	C10—C11—H11A	118.9
C1—C2—C3	117.18 (14)	C13—C12—C11	119.26 (11)
C1—C2—C16	121.70 (13)	C13—C12—H12A	120.4
C3—C2—C16	121.11 (14)	C11—C12—H12A	120.4
C4—C3—C2	122.06 (15)	O3—C13—C12	124.53 (11)
C4—C3—H3A	119.0	O3—C13—C14	115.97 (11)
C2—C3—H3A	119.0	C12—C13—C14	119.50 (12)
C3—C4—C5	120.69 (14)	C15—C14—C13	120.86 (12)
C3—C4—H4A	119.7	C15—C14—H14A	119.6
C5—C4—H4A	119.7	C13—C14—H14A	119.6
O1—C5—C4	118.37 (13)	C14—C15—C10	120.80 (12)
O1—C5—C6	122.08 (14)	C14—C15—H15A	119.6
C4—C5—C6	119.54 (14)	C10—C15—H15A	119.6
C1—C6—C5	117.70 (12)	C2—C16—H16A	109.5
C1—C6—C7	122.80 (11)	C2—C16—H16B	109.5
C5—C6—C7	119.49 (12)	H16A—C16—H16B	109.5
O2—C7—C8	119.66 (12)	C2—C16—H16C	109.5
O2—C7—C6	119.25 (12)	H16A—C16—H16C	109.5
C8—C7—C6	121.09 (11)	H16B—C16—H16C	109.5
C9—C8—C7	120.81 (12)	O3—C17—H17A	109.5
C9—C8—H8A	119.6	O3—C17—H17B	109.5
C7—C8—H8A	119.6	H17A—C17—H17B	109.5
C8—C9—C10	128.35 (12)	O3—C17—H17C	109.5
C8—C9—H9A	115.8	H17A—C17—H17C	109.5
C10—C9—H9A	115.8	H17B—C17—H17C	109.5
C11—C10—C15	117.30 (12)
C6—C1—C2—C3	1.0 (2)	O2—C7—C8—C9	3.8 (2)
C6—C1—C2—C16	−177.83 (13)	C6—C7—C8—C9	−176.22 (12)
C1—C2—C3—C4	−1.3 (2)	C7—C8—C9—C10	−178.59 (12)
C16—C2—C3—C4	177.45 (14)	C8—C9—C10—C11	178.78 (13)
C2—C3—C4—C5	0.5 (3)	C8—C9—C10—C15	−0.7 (2)
C3—C4—C5—O1	−178.70 (15)	C15—C10—C11—C12	−0.5 (2)
C3—C4—C5—C6	0.7 (2)	C9—C10—C11—C12	−179.97 (12)
C2—C1—C6—C5	0.22 (19)	C10—C11—C12—C13	−0.4 (2)
C2—C1—C6—C7	179.43 (12)	C17—O3—C13—C12	0.6 (2)
O1—C5—C6—C1	178.32 (12)	C17—O3—C13—C14	−179.83 (13)
C4—C5—C6—C1	−1.1 (2)	C11—C12—C13—O3	−179.21 (13)
O1—C5—C6—C7	−0.9 (2)	C11—C12—C13—C14	1.2 (2)
C4—C5—C6—C7	179.72 (13)	O3—C13—C14—C15	179.21 (13)
C1—C6—C7—O2	−178.73 (13)	C12—C13—C14—C15	−1.2 (2)
C5—C6—C7—O2	0.47 (19)	C13—C14—C15—C10	0.3 (2)
C1—C6—C7—C8	1.27 (19)	C11—C10—C15—C14	0.5 (2)
C5—C6—C7—C8	−179.54 (12)	C9—C10—C15—C14	179.98 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.95 (2)	1.65 (2)	2.5112 (18)	149.4 (19)
C11—H11A···O3^i	0.93	2.60	3.4317 (17)	149
C16—H16C···Cg1^ii	0.96	2.81	3.5800 (18)	138

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