(2E)-3-(4-Chloro­phen­yl)-1-(4-hy­droxy­phen­yl)prop-2-en-1-one

In the title compound, C₁₅H₁₁ClO₂, the dihedral angle between the mean planes of the chloro­benzene and hy­droxy­benzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group makes an angle of 18.0 (1)° with the hy­droxy­phenyl ring and 11.5 (1)° with the chloro­phenyl ring. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds, weak C—H...O, C—H...π and π–π stacking inter­actions [centroid–centroid distances = 3.7771 (7) and 3.6917 (7) Å].

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.041
• wR factor = 0.115
• Data-to-parameter ratio = 24.5

checkCIF/PLATON results

No syntax errors found





Alert level A
PLAT900_ALERT_1_A No Matching Reflection File Found ..............          !
PLAT900_ALERT_1_A No Matching Reflection File Found ..............          !
PLAT902_ALERT_1_A No (Interpretable) Reflections found in FCF ....          !

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
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C15 H11 Cl O2

Alert level G
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n

   3 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 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

   3 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
   0 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

Chalcones, or 1,3-diaryl-2-propen-1-ones, belong to the flavonoid family. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives. Chalcones have been reported to possess many useful properties, including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Nowakowska, 2007). Certain chalcone derivatives are reported to inhibit the polymerization of tubulin to form microtubules and are therefore antimitotic agents which can be used as antigout agents. The chalcone derivatives are also reported to inhibit the destruction of the myelin sheath in the central nervous system of multiple sclerosis patients and are thus useful in controlling the progressive nature of the disease (Edwards et al., 1989).

In a continuation of our studies on the crystal structures of chalcones (Jasinski et al., 2010, 2011a, 2011b), we report here the synthesis and crystal structure of the title compound, C₁₅H₁₁ClO₂, (I), Fig. 2. The dihedral angle between the mean planes of the chlorobenzene and hydroxybenzene rings is 6.5 (6)°. The mean plane of the prop-2-en-1-one group, the active site in this molecule, makes angles of 18.0 (1)° with the hydroxy benzene and 11.5 (1)° with the chlorobenzene rings, respectively. Bond lengths are normal (Allen et al., 1987) and correspond to those observed in related compounds (Butcher et al., 2007a, 2007b; Narayana et al., 2007; Sarojini et al., 2007a, 2007b). Crystal packing is stabilized by O—H···O hydrogen bonds, weak C—H···O, C—H···Cg π—ring (Table 1) and π—π intermolecular stacking interactions (Table 2 & Fig. 3).

Related literature

For the biological properties of chalcones, see: Nowakowska (2007) and for their role in tubulin polymerization inhibition, see: Edwards et al. (1989). For related structures, see: Jasinski et al. (2010, 2011a,b); Butcher et al. (2007a,b); Narayana et al. (2007); Sarojini et al. (2007a,b). For standard bond lengths, see: Allen et al., (1987).

S2. Experimental

4-Hydroxyacetophenone (1.36 g, 0.01 mol) was mixed with 4-chlorobenzaldeyde (1.40 g, 0.01 mol) and dissolved in ethanol (20 ml) (Fig. 1). To this solution 4 ml of KOH (50%) (10 mL) was added at 0°C. The reaction mixture was stirred for 4 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. Crystals suitable for x-ray diffraction studies were grown by the slow evaporation of the solution of the compound in acetone. M.P:419 K. Composition: Found (Calculated) for C₁₅H₁₁ClO₂, C: 69.53 (69.64); H: 4.26 (4.29).

S3. Refinement

The hydroxyl hydrogem (H1O) was located by a Fourier map, fixed at 0.84 Å and refined using the riding model. All of the remaining H atoms were placed in their calculated positions and then refined using the riding model with Atom—H lengths of 0.95Å (CH). Isotropic displacement parameters for these atoms were set to 1.18–1.21 (CH) or 1.18 (OH) times U_eq of the parent atom.

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures

	Fig. 1. Reaction scheme for the preparation of (I).
	Fig. 2. Molecular structure of the title compound showing the atom labeling scheme and 50% probability displacement ellipsoids.
	Fig. 3. Packing diagram of the title compound viewed down the a axis. Dashed lines indicate O—H···O hydrogen bonds and weak C—H···O intermolecular interactions.

(2E)-3-(4-Chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one

Crystal data

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.422 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4738 reflections
a = 7.3570 (2) Å	θ = 4.7–32.4°
b = 15.6450 (5) Å	µ = 0.31 mm^−1
c = 10.4954 (3) Å	T = 200 K
β = 90.518 (3)°	Irregular chunk, colorless
V = 1207.97 (6) Å^3	0.51 × 0.45 × 0.36 mm
Z = 4

Data collection

Oxford Diffraction Gemini diffractometer	4020 independent reflections
Radiation source: fine-focus sealed tube	2924 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.6°, θmin = 4.7°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −23→17
Tmin = 0.984, Tmax = 1.000	l = −11→15
10126 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.115	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0648P)^2] where P = (Fo^2 + 2Fc^2)/3
4020 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.38 e Å^−3
0 restraints	Δρmin = −0.19 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
Cl	0.13335 (5)	0.12309 (2)	0.03417 (3)	0.03910 (12)
O1	0.83226 (11)	−0.31714 (6)	−0.88736 (8)	0.0269 (2)
H1O	0.7288	−0.3393	−0.8952	0.032*
O2	1.03166 (11)	−0.08981 (6)	−0.40899 (9)	0.0300 (2)
C1	0.86149 (15)	−0.16357 (7)	−0.56445 (10)	0.0217 (2)
C2	1.01626 (15)	−0.18219 (7)	−0.63990 (11)	0.0233 (2)
H2A	1.1307	−0.1587	−0.6162	0.028*
C3	1.00442 (15)	−0.23337 (7)	−0.74638 (11)	0.0240 (2)
H3A	1.1090	−0.2440	−0.7964	0.029*
C4	0.83821 (15)	−0.26923 (7)	−0.77995 (11)	0.0218 (2)
C5	0.68456 (15)	−0.25387 (8)	−0.70399 (11)	0.0249 (2)
H5A	0.5718	−0.2800	−0.7253	0.030*
C6	0.69667 (15)	−0.20111 (8)	−0.59876 (11)	0.0250 (2)
H6A	0.5916	−0.1903	−0.5494	0.030*
C7	0.88030 (15)	−0.10548 (7)	−0.45464 (11)	0.0228 (2)
C8	0.71613 (16)	−0.06563 (8)	−0.39876 (11)	0.0257 (2)
H8A	0.5998	−0.0789	−0.4335	0.031*
C9	0.72854 (16)	−0.01152 (7)	−0.30074 (11)	0.0244 (2)
H9A	0.8482	0.0042	−0.2753	0.029*
C10	0.57985 (15)	0.02682 (7)	−0.22700 (11)	0.0232 (2)
C11	0.39739 (16)	0.00729 (8)	−0.25006 (12)	0.0269 (3)
H11A	0.3655	−0.0270	−0.3215	0.032*
C12	0.26083 (16)	0.03728 (8)	−0.16994 (12)	0.0286 (3)
H12A	0.1376	0.0221	−0.1856	0.034*
C13	0.30593 (17)	0.08902 (8)	−0.06791 (11)	0.0267 (3)
C14	0.48422 (18)	0.11178 (8)	−0.04434 (12)	0.0296 (3)
H14A	0.5144	0.1483	0.0250	0.036*
C15	0.61975 (17)	0.08026 (8)	−0.12423 (12)	0.0277 (3)
H15A	0.7427	0.0957	−0.1080	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0429 (2)	0.0418 (2)	0.03272 (18)	0.01436 (15)	0.01185 (14)	0.00176 (13)
O1	0.0232 (4)	0.0314 (5)	0.0261 (4)	−0.0042 (3)	0.0043 (3)	−0.0055 (3)
O2	0.0223 (4)	0.0345 (5)	0.0330 (5)	0.0028 (4)	−0.0034 (3)	−0.0045 (4)
C1	0.0207 (5)	0.0229 (5)	0.0216 (5)	0.0009 (4)	0.0022 (4)	0.0022 (4)
C2	0.0175 (5)	0.0265 (6)	0.0259 (6)	−0.0006 (4)	0.0006 (4)	0.0022 (5)
C3	0.0190 (5)	0.0280 (6)	0.0250 (6)	0.0004 (4)	0.0053 (4)	0.0015 (4)
C4	0.0236 (5)	0.0218 (5)	0.0203 (5)	0.0008 (4)	0.0022 (4)	0.0034 (4)
C5	0.0185 (5)	0.0296 (6)	0.0265 (6)	−0.0049 (4)	0.0031 (4)	0.0009 (5)
C6	0.0204 (5)	0.0296 (6)	0.0250 (6)	−0.0003 (4)	0.0057 (4)	0.0003 (5)
C7	0.0219 (5)	0.0241 (6)	0.0226 (5)	0.0012 (4)	0.0013 (4)	0.0033 (4)
C8	0.0203 (5)	0.0312 (6)	0.0257 (6)	0.0018 (5)	−0.0001 (4)	−0.0020 (5)
C9	0.0221 (5)	0.0250 (6)	0.0262 (6)	−0.0004 (4)	−0.0004 (4)	0.0004 (5)
C10	0.0243 (5)	0.0210 (5)	0.0241 (5)	0.0009 (4)	0.0001 (4)	−0.0003 (4)
C11	0.0265 (6)	0.0274 (6)	0.0267 (6)	0.0013 (5)	−0.0025 (5)	−0.0048 (5)
C12	0.0226 (6)	0.0319 (6)	0.0312 (6)	0.0027 (5)	−0.0010 (5)	−0.0002 (5)
C13	0.0311 (6)	0.0239 (6)	0.0251 (6)	0.0074 (5)	0.0041 (5)	0.0028 (5)
C14	0.0381 (7)	0.0244 (6)	0.0263 (6)	0.0012 (5)	−0.0021 (5)	−0.0048 (5)
C15	0.0273 (6)	0.0268 (6)	0.0290 (6)	−0.0029 (5)	−0.0031 (5)	−0.0029 (5)

Geometric parameters (Å, º)

Cl—C13	1.7517 (12)	C7—C8	1.4846 (15)
O1—C4	1.3541 (14)	C8—C9	1.3348 (16)
O1—H1O	0.8400	C8—H8A	0.9500
O2—C7	1.2328 (14)	C9—C10	1.4734 (15)
C1—C6	1.3917 (16)	C9—H9A	0.9500
C1—C2	1.4230 (14)	C10—C15	1.3939 (16)
C1—C7	1.4733 (16)	C10—C11	1.3957 (17)
C2—C3	1.3770 (16)	C11—C12	1.3971 (16)
C2—H2A	0.9500	C11—H11A	0.9500
C3—C4	1.3879 (16)	C12—C13	1.3804 (18)
C3—H3A	0.9500	C12—H12A	0.9500
C4—C5	1.4098 (15)	C13—C14	1.3793 (18)
C5—C6	1.3811 (17)	C14—C15	1.3984 (17)
C5—H5A	0.9500	C14—H14A	0.9500
C6—H6A	0.9500	C15—H15A	0.9500
C4—O1—H1O	109.5	C9—C8—H8A	119.3
C6—C1—C2	117.99 (10)	C7—C8—H8A	119.3
C6—C1—C7	122.56 (10)	C8—C9—C10	128.11 (11)
C2—C1—C7	119.45 (10)	C8—C9—H9A	115.9
C3—C2—C1	121.71 (10)	C10—C9—H9A	115.9
C3—C2—H2A	119.1	C15—C10—C11	117.45 (10)
C1—C2—H2A	119.1	C15—C10—C9	119.90 (11)
C2—C3—C4	119.35 (10)	C11—C10—C9	122.49 (11)
C2—C3—H3A	120.3	C10—C11—C12	121.18 (11)
C4—C3—H3A	120.3	C10—C11—H11A	119.4
O1—C4—C3	117.18 (10)	C12—C11—H11A	119.4
O1—C4—C5	123.03 (10)	C13—C12—C11	119.66 (11)
C3—C4—C5	119.78 (10)	C13—C12—H12A	120.2
C6—C5—C4	120.52 (11)	C11—C12—H12A	120.2
C6—C5—H5A	119.7	C14—C13—C12	120.79 (11)
C4—C5—H5A	119.7	C14—C13—Cl	120.34 (10)
C5—C6—C1	120.59 (10)	C12—C13—Cl	118.84 (10)
C5—C6—H6A	119.7	C13—C14—C15	118.92 (12)
C1—C6—H6A	119.7	C13—C14—H14A	120.5
O2—C7—C1	120.32 (10)	C15—C14—H14A	120.5
O2—C7—C8	119.88 (11)	C10—C15—C14	121.95 (11)
C1—C7—C8	119.80 (10)	C10—C15—H15A	119.0
C9—C8—C7	121.37 (11)	C14—C15—H15A	119.0
C6—C1—C2—C3	2.13 (17)	C1—C7—C8—C9	−178.78 (11)
C7—C1—C2—C3	−177.42 (11)	C7—C8—C9—C10	−173.67 (11)
C1—C2—C3—C4	−1.28 (17)	C8—C9—C10—C15	177.89 (12)
C2—C3—C4—O1	178.21 (10)	C8—C9—C10—C11	2.43 (19)
C2—C3—C4—C5	−0.86 (17)	C15—C10—C11—C12	−2.62 (18)
O1—C4—C5—C6	−176.85 (11)	C9—C10—C11—C12	172.94 (12)
C3—C4—C5—C6	2.17 (18)	C10—C11—C12—C13	1.71 (19)
C4—C5—C6—C1	−1.29 (18)	C11—C12—C13—C14	0.26 (19)
C2—C1—C6—C5	−0.81 (17)	C11—C12—C13—Cl	−178.00 (10)
C7—C1—C6—C5	178.72 (11)	C12—C13—C14—C15	−1.18 (19)
C6—C1—C7—O2	162.67 (11)	Cl—C13—C14—C15	177.05 (10)
C2—C1—C7—O2	−17.81 (17)	C11—C10—C15—C14	1.68 (18)
C6—C1—C7—C8	−17.34 (17)	C9—C10—C15—C14	−174.00 (11)
C2—C1—C7—C8	162.18 (11)	C13—C14—C15—C10	0.19 (19)
O2—C7—C8—C9	1.20 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.84	1.83	2.6556 (12)	167
C6—H6A···O1^ii	0.95	2.57	3.5070 (13)	169
C11—H11A···O1^ii	0.95	2.55	3.3382 (15)	141
C14—H14A···Cg1^iii	0.95	2.79	3.7090 (14)	163

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