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

Two new chalcones of general type (2E)-1-(3-hydroxy­phen­yl)-3-(4-R-phen­yl)prop-2-en-1-one are reported, one where R = chloro, C₁₅H₁₁ClO₂, in the present paper, and one where R = methyl, C₁₆H₁₄O₂, in the preceding paper [Butcher, Jasinski, Narayana, Lakshmana & Yathirajan (2007). Acta Cryst. E63, o3660]. In both structures, the 3-hydroxy­phenyl and 4-(meth­yl/chloro)phenyl groups are coplanar with each other and also with the propyl-2-ketone oxygen. Crystal packing is stabilized by inter­molecular O—H...O hydrogen bonding between the hydroxyl hydrogen and the propyl-2-ketone oxygen.

Key indicators

• Single-crystal X-ray study
• T = 203 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.056
• wR factor = 0.176
• Data-to-parameter ratio = 24.8

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.480     0.950
            Tmin(prime) and Tmax expected:      0.864     0.949
            RR(prime) =      0.556
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.55

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.07
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 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
   2 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

---

S1. Comment

Two new chalcones of general formula (2E)-1-(3-Hydroxyphenyl)-3-(4-R-phenyl)prop-2-en-1-one are reported, the one with R=Chloro (C₁₅H₁₁ClO₂) (II) in the present paper, the one with R=methyl (C₁₆H₁₄O₂) (I) in the preceeding one (Butcher et al., 2007) to which the reader is referred for a general introduction.

Fig. 1 presents a molecular diagram for (II).

The 3-hydroxyphenyl and 4-chlorophenyl groups are coplanar with each other and with the propyl 2 ketone group forming torsion angles 2.3 (3)°, C8—C9—C10—C11, and -2.7 (2)°, C8—C7—C1—C6, respectively.

Intermolecular O—H···O hydrogen bonding interactions involving the H1 hydroxyl atom and prop-2-en O2 atom (Table 1) link the molecules (almost perpendicular to each other) into a planar array (Fig. 2).

In spite of crystallizing in different space groups ((I) in P21/n, (II) in P21/c) both compounds are very nealy isostructural.

Related literature

For the R = methyl structure, see Butcher et al. (2007).

S2. Experimental

To a mixture of 1-(3-hydroxyphenyl)ethanone (1.36 g, 0.01 mol) and 4-chloroacetophenone (1.4 g, 0.01 mol) in ethanol (25 ml), a solution of potassium hydroxide (5%, 7.5 ml) was added slowly with stirring. The mixture was stirred at room temperature for 6 h. The precipitated solid was filtered, washed with cold ethanol, dried and recrystallized from ethanol and the crystals were obtained from acetone by slow evaporation (yield: 78%; m.p.:425–426 K). Elemental analysis found: C: 69.52, H: 4.23%. C₁₅H₁₁ClO₂ requires C, 69.64, H: 4.29%.

S3. Refinement

The larger than expected transmission factors range is probably due to inferior data quality and to the fact that the multi-scan correction deals with a number of factors, of which absorption is only one. All of the H atoms, except H1 which was located from a difference Fourier map, were inferred from neighbouring sites. All H atoms were included in the riding model approximation with C—H = 0.94 Å, and with U_iso(H) = 1.19–1.20U_eq(C,O).

Computing details

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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

	Fig. 1. Molecular structure of (II), showing atom labelling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (II) viewed down the a axis. Dashed lines indicate O–H···O hydrogen bonds. Symmetry code: as in Table 1

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

Crystal data

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.420 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 1 2ybc '	Cell parameters from 5848 reflections
a = 7.5910 (7) Å	θ = 4.7–32.4°
b = 10.8509 (7) Å	µ = 0.31 mm^−1
c = 15.1544 (11) Å	T = 203 K
β = 104.213 (8)°	Plate, colorless
V = 1210.05 (16) Å^3	0.47 × 0.38 × 0.17 mm
Z = 4

Data collection

Oxford Diffraction Gemini R diffractometer	4072 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.069
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.6°, θmin = 4.7°
φ and ω scans	h = −11→10
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −16→15
Tmin = 0.48, Tmax = 0.95	l = −22→22
15403 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.176	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.1075P)^2] where P = (Fo^2 + 2Fc^2)/3
4072 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.75 e Å^−3
0 restraints	Δρmin = −0.36 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	0.51228 (7)	0.67123 (5)	0.02769 (3)	0.0498 (2)
O1	1.10564 (19)	0.18538 (12)	0.82766 (8)	0.0408 (3)
H1	1.1559	0.1197	0.8478	0.049*
O2	0.75857 (17)	0.46703 (11)	0.60068 (8)	0.0371 (3)
C1	0.9418 (2)	0.29521 (14)	0.59612 (11)	0.0275 (3)
C2	0.9721 (2)	0.28277 (15)	0.69002 (11)	0.0293 (4)
H2A	0.9177	0.3384	0.7228	0.035*
C3	1.0821 (2)	0.18899 (15)	0.73585 (11)	0.0308 (4)
C4	1.1593 (2)	0.10554 (15)	0.68772 (13)	0.0369 (4)
H4A	1.2330	0.0416	0.7184	0.044*
C5	1.1278 (3)	0.11638 (16)	0.59428 (13)	0.0394 (4)
H5A	1.1796	0.0588	0.5617	0.047*
C6	1.0214 (2)	0.21064 (16)	0.54781 (12)	0.0348 (4)
H6A	1.0028	0.2178	0.4844	0.042*
C7	0.8283 (2)	0.39982 (14)	0.55349 (10)	0.0270 (3)
C8	0.7987 (2)	0.42422 (14)	0.45573 (10)	0.0275 (3)
H8A	0.8609	0.3770	0.4210	0.033*
C9	0.6852 (2)	0.51211 (14)	0.41560 (10)	0.0277 (3)
H9A	0.6264	0.5566	0.4533	0.033*
C10	0.6412 (2)	0.54776 (13)	0.31968 (10)	0.0260 (3)
C11	0.7139 (2)	0.48648 (15)	0.25585 (11)	0.0307 (4)
H11A	0.7919	0.4190	0.2745	0.037*
C12	0.6737 (2)	0.52297 (16)	0.16603 (11)	0.0340 (4)
H12A	0.7233	0.4810	0.1235	0.041*
C13	0.5594 (2)	0.62216 (16)	0.13965 (11)	0.0322 (4)
C14	0.4848 (2)	0.68418 (15)	0.20078 (13)	0.0342 (4)
H14A	0.4059	0.7510	0.1816	0.041*
C15	0.5269 (2)	0.64728 (15)	0.29067 (12)	0.0326 (4)
H15A	0.4774	0.6902	0.3328	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0649 (4)	0.0536 (3)	0.0289 (2)	0.0138 (2)	0.0080 (2)	0.00854 (19)
O1	0.0468 (8)	0.0458 (7)	0.0286 (6)	−0.0020 (6)	0.0068 (6)	0.0106 (5)
O2	0.0450 (8)	0.0380 (6)	0.0314 (6)	0.0067 (5)	0.0150 (5)	−0.0010 (5)
C1	0.0273 (8)	0.0277 (7)	0.0269 (8)	−0.0065 (6)	0.0057 (6)	0.0011 (6)
C2	0.0294 (9)	0.0313 (8)	0.0283 (8)	−0.0077 (6)	0.0089 (7)	0.0009 (6)
C3	0.0295 (9)	0.0364 (9)	0.0267 (8)	−0.0096 (7)	0.0073 (6)	0.0062 (6)
C4	0.0334 (10)	0.0346 (9)	0.0425 (10)	0.0024 (7)	0.0092 (8)	0.0111 (8)
C5	0.0436 (11)	0.0353 (9)	0.0426 (10)	0.0070 (8)	0.0169 (8)	0.0024 (8)
C6	0.0393 (10)	0.0352 (9)	0.0312 (8)	0.0029 (7)	0.0114 (7)	0.0017 (7)
C7	0.0270 (8)	0.0284 (7)	0.0263 (8)	−0.0071 (6)	0.0079 (6)	−0.0008 (6)
C8	0.0308 (9)	0.0270 (7)	0.0254 (7)	−0.0026 (6)	0.0084 (6)	−0.0008 (6)
C9	0.0296 (9)	0.0283 (8)	0.0262 (7)	−0.0026 (6)	0.0086 (6)	−0.0017 (6)
C10	0.0260 (8)	0.0260 (7)	0.0267 (7)	−0.0030 (6)	0.0077 (6)	0.0004 (6)
C11	0.0299 (9)	0.0326 (8)	0.0290 (7)	0.0060 (7)	0.0060 (6)	0.0030 (7)
C12	0.0350 (10)	0.0395 (9)	0.0288 (8)	0.0050 (7)	0.0102 (7)	−0.0031 (7)
C13	0.0343 (9)	0.0345 (9)	0.0262 (8)	−0.0001 (7)	0.0044 (7)	0.0020 (6)
C14	0.0324 (9)	0.0323 (8)	0.0376 (9)	0.0071 (7)	0.0080 (7)	0.0046 (7)
C15	0.0352 (10)	0.0305 (8)	0.0346 (9)	0.0044 (7)	0.0132 (7)	−0.0005 (7)

Geometric parameters (Å, º)

Cl—C13	1.7298 (16)	C7—C8	1.467 (2)
O1—C3	1.3591 (19)	C8—C9	1.328 (2)
O1—H1	0.8300	C8—H8A	0.9400
O2—C7	1.2284 (19)	C9—C10	1.461 (2)
C1—C2	1.391 (2)	C9—H9A	0.9400
C1—C6	1.400 (2)	C10—C15	1.387 (2)
C1—C7	1.475 (2)	C10—C11	1.395 (2)
C2—C3	1.389 (2)	C11—C12	1.378 (2)
C2—H2A	0.9400	C11—H11A	0.9400
C3—C4	1.380 (3)	C12—C13	1.379 (2)
C4—C5	1.382 (3)	C12—H12A	0.9400
C4—H4A	0.9400	C13—C14	1.374 (2)
C5—C6	1.384 (2)	C14—C15	1.380 (2)
C5—H5A	0.9400	C14—H14A	0.9400
C6—H6A	0.9400	C15—H15A	0.9400
C3—O1—H1	109.5	C9—C8—H8A	119.6
C2—C1—C6	119.13 (15)	C7—C8—H8A	119.6
C2—C1—C7	117.06 (14)	C8—C9—C10	127.58 (14)
C6—C1—C7	123.80 (14)	C8—C9—H9A	116.2
C3—C2—C1	120.71 (15)	C10—C9—H9A	116.2
C3—C2—H2A	119.6	C15—C10—C11	118.34 (14)
C1—C2—H2A	119.6	C15—C10—C9	119.59 (14)
O1—C3—C4	123.78 (16)	C11—C10—C9	122.06 (14)
O1—C3—C2	116.41 (15)	C12—C11—C10	121.24 (15)
C4—C3—C2	119.82 (15)	C12—C11—H11A	119.4
C3—C4—C5	119.78 (16)	C10—C11—H11A	119.4
C3—C4—H4A	120.1	C11—C12—C13	118.80 (15)
C5—C4—H4A	120.1	C11—C12—H12A	120.6
C4—C5—C6	121.12 (17)	C13—C12—H12A	120.6
C4—C5—H5A	119.4	C14—C13—C12	121.39 (15)
C6—C5—H5A	119.4	C14—C13—Cl	119.36 (13)
C5—C6—C1	119.42 (16)	C12—C13—Cl	119.23 (13)
C5—C6—H6A	120.3	C13—C14—C15	119.30 (16)
C1—C6—H6A	120.3	C13—C14—H14A	120.3
O2—C7—C8	119.99 (15)	C15—C14—H14A	120.3
O2—C7—C1	119.39 (14)	C14—C15—C10	120.92 (15)
C8—C7—C1	120.62 (13)	C14—C15—H15A	119.5
C9—C8—C7	120.88 (14)	C10—C15—H15A	119.5
C6—C1—C2—C3	1.0 (2)	C1—C7—C8—C9	174.62 (15)
C7—C1—C2—C3	−178.02 (14)	C7—C8—C9—C10	179.95 (14)
C1—C2—C3—O1	179.11 (14)	C8—C9—C10—C15	−176.19 (16)
C1—C2—C3—C4	−1.3 (2)	C8—C9—C10—C11	2.3 (3)
O1—C3—C4—C5	−179.99 (16)	C15—C10—C11—C12	−0.2 (3)
C2—C3—C4—C5	0.5 (3)	C9—C10—C11—C12	−178.68 (15)
C3—C4—C5—C6	0.7 (3)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C1	−1.1 (3)	C11—C12—C13—C14	−0.4 (3)
C2—C1—C6—C5	0.3 (2)	C11—C12—C13—Cl	178.41 (13)
C7—C1—C6—C5	179.16 (16)	C12—C13—C14—C15	0.8 (3)
C2—C1—C7—O2	−3.6 (2)	Cl—C13—C14—C15	−178.03 (14)
C6—C1—C7—O2	177.48 (15)	C13—C14—C15—C10	−0.9 (3)
C2—C1—C7—C8	176.21 (14)	C11—C10—C15—C14	0.6 (3)
C6—C1—C7—C8	−2.7 (2)	C9—C10—C15—C14	179.11 (15)
O2—C7—C8—C9	−5.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.83	1.88	2.7029 (18)	172.2

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