(2E)-3-(2-Chloro­phen­yl)-1-phenyl­prop-2-en-1-one

In the title mol­ecule, C₁₅H₁₁ClO, the angle between the mean planes of the two rings is 6.6 (8)°. The crystal packing is stabilized by van der Waals inter­actions, whereby the mol­ecules are aligned in rows in a zigzag pattern.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.086
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.90

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.905
            Tmax scaled      0.905 Tmin scaled      0.817
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           32.42
           From the CIF: _reflns_number_total               2120
           Count of symmetry unique reflns         2284
           Completeness (_total/calc)             92.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present        yes
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcone is a unique template molecule that is associated with several biological activities. Chalcone and its analogues are relatively easily available, not only by isolation from natural products but also by classical and combinatorial synthesis. The cytotoxic, anticancer, antiviral, antiprotozoal, insecticidal, chemopreventative, mutagenic and enzyme-inhibitory properties of a number of chalcones have been reviewed (Dimmock et al., 1999; Go et al., 2005). The antifungal and antibacterial activities of these compounds have also been reviewed (Opletalova & Sedivy, 1999; Opletalova, 2000). Chalcones and their analogues are also used as potential therapeutic agents in diseases of the cardiovascular system. The stabilizing action of chalcones on the vascular wall, vasodilating and antioxidative activity have been reported (Opletalova et al., 2003). The crystal structures of 1-phenyl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (Teh et al., 2006); 1-(2,4-dichlorophenyl)-3-[4-(methylsalfanyl)phenyl]prop-2-en-1-one (Butcher et al. 2007b); 1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one, (Yathirajan et al., 2007); 3-(4-chlorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one (Butcher et al. 2007a). As a part of our ongoing studies on chalcones, a new chalcone, C₁₅H₁₁ClO, was prepared and the crystal structure is reported.

In the title molecule, C₁₅H₁₁ClO, the angle between the mean planes of the 2-chlorophenyl-imino and phenol groups is 6.6 (8)° (Fig 1). Crystal packing is stabilized by van der Waals interactions, whereby the molecules are aligned in rows in a zigzag pattern with the phenyl rings diagonal to the ac face of the unit cell (Fig 2).

Related literature

For related structures, see: Teh et al. (2006); Butcher, Jasinski et al. (2007); Butcher, Yathirajan et al. (2007); Yathirajan et al. (2007). For related literature, see: Dimmock et al. (1999); Go et al. (2005); Opletalova & Sedivy, (1999); Opletalova, (2000); Opletalova et al., (2003).

S2. Experimental

A mixture of acetophenone (1.2 g, 0.01 mol) and 2-chlorobenzaldehyde (1.3 g, 0.01 mol) was stirred well. Sodium hydroxide (4 ml, 5%) was added and the mixture was stirred for 6 hrs. The separated precipitate was washed, dried and recrystallized from ethyl alcohol. (m.p.:318 K). Analysis found: C: 74.10, H: 4.51%; C₁₅H₁₁ClO requires C: 74.23, H: 4.57%.

S3. Refinement

The H atoms were placed in their calculated positions and then refined using the riding model with C—H = 0.93 Å, and with U_iso(H) = 1.18–1.20U_eq(C).

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: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures

	Fig. 1. Molecular structure of the title compound, showing atom labeling and 50% probability displacement ellipsoids.
	Fig. 2. Packing diagram of the title compound, viewed down the c axis.
	Fig. 3. Synthetic scheme for C15H11ClO.

(2E)-3-(2-Chlorophenyl)-1-phenylprop-2-en-1-one

Crystal data

C15H11ClO	F(000) = 504
Mr = 242.69	Dx = 1.323 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3012 reflections
a = 19.0061 (7) Å	θ = 4.8–32.4°
b = 5.0646 (3) Å	µ = 0.29 mm^−1
c = 12.6534 (4) Å	T = 296 K
V = 1217.99 (9) Å^3	Prism, colorless
Z = 4	0.48 × 0.45 × 0.34 mm

Data collection

Oxford Diffraction Gemini R CCD diffractometer	2120 independent reflections
Radiation source: fine-focus sealed tube	1286 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.5081 pixels mm^-1	θmax = 32.4°, θmin = 4.8°
ϕ and ω scans	h = −27→27
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −7→7
Tmin = 0.903, Tmax = 1.000	l = −18→17
7585 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.087	w = 1/[σ^2(Fo^2) + (0.0482P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
2120 reflections	Δρmax = 0.20 e Å^−3
154 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983), 2120 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (7)

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	0.68430 (3)	0.75899 (13)	0.51978 (6)	0.0616 (2)
O	0.49895 (9)	0.0827 (4)	0.52181 (13)	0.0684 (5)
C1	0.44116 (9)	−0.1047 (4)	0.66737 (15)	0.0334 (4)
C2	0.40315 (10)	−0.2764 (4)	0.60322 (17)	0.0388 (5)
H2A	0.4094	−0.2711	0.5304	0.047*
C3	0.35630 (10)	−0.4545 (4)	0.64633 (18)	0.0448 (5)
H3A	0.3310	−0.5676	0.6026	0.054*
C4	0.34697 (11)	−0.4646 (4)	0.7546 (2)	0.0498 (6)
H4A	0.3158	−0.5856	0.7839	0.060*
C5	0.38403 (12)	−0.2949 (4)	0.81904 (18)	0.0482 (5)
H5A	0.3776	−0.3007	0.8919	0.058*
C6	0.43057 (10)	−0.1169 (4)	0.77580 (16)	0.0410 (5)
H6A	0.4553	−0.0031	0.8199	0.049*
C7	0.49182 (9)	0.0816 (4)	0.61733 (15)	0.0388 (5)
C8	0.53307 (11)	0.2646 (4)	0.68406 (16)	0.0399 (5)
H8A	0.5279	0.2545	0.7570	0.048*
C9	0.57618 (10)	0.4390 (4)	0.64553 (17)	0.0422 (5)
H9A	0.5806	0.4423	0.5723	0.051*
C10	0.61854 (9)	0.6302 (4)	0.70391 (15)	0.0356 (4)
C11	0.66921 (10)	0.7863 (4)	0.65482 (17)	0.0394 (5)
C12	0.70887 (10)	0.9688 (4)	0.70996 (18)	0.0445 (5)
H12A	0.7424	1.0700	0.6749	0.053*
C13	0.69862 (10)	1.0003 (5)	0.81699 (18)	0.0471 (5)
H13A	0.7252	1.1226	0.8545	0.057*
C14	0.64873 (11)	0.8496 (5)	0.86826 (17)	0.0482 (5)
H14A	0.6417	0.8703	0.9405	0.058*
C15	0.60925 (11)	0.6678 (4)	0.81245 (16)	0.0422 (5)
H15A	0.5757	0.5680	0.8480	0.051*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0590 (3)	0.0823 (4)	0.0435 (2)	−0.0241 (3)	0.0095 (3)	−0.0010 (3)
O	0.0775 (10)	0.0902 (14)	0.0374 (7)	−0.0422 (10)	0.0054 (9)	−0.0072 (10)
C1	0.0303 (8)	0.0295 (10)	0.0404 (10)	0.0045 (7)	−0.0038 (7)	0.0000 (9)
C2	0.0374 (10)	0.0380 (11)	0.0411 (10)	0.0062 (8)	−0.0063 (8)	−0.0024 (9)
C3	0.0395 (10)	0.0374 (12)	0.0574 (13)	−0.0016 (9)	−0.0087 (10)	−0.0063 (10)
C4	0.0452 (11)	0.0409 (12)	0.0634 (15)	−0.0068 (10)	−0.0008 (11)	0.0077 (12)
C5	0.0526 (13)	0.0512 (14)	0.0409 (10)	−0.0068 (11)	−0.0004 (9)	0.0084 (11)
C6	0.0449 (10)	0.0356 (10)	0.0424 (10)	−0.0037 (9)	−0.0053 (9)	0.0012 (10)
C7	0.0340 (9)	0.0401 (12)	0.0422 (10)	0.0007 (8)	−0.0015 (8)	0.0004 (10)
C8	0.0415 (10)	0.0399 (12)	0.0384 (10)	−0.0030 (9)	−0.0033 (8)	0.0003 (10)
C9	0.0424 (10)	0.0487 (13)	0.0355 (9)	−0.0066 (10)	0.0025 (8)	−0.0022 (9)
C10	0.0307 (9)	0.0358 (10)	0.0403 (10)	0.0022 (8)	−0.0022 (8)	0.0042 (10)
C11	0.0331 (9)	0.0445 (12)	0.0406 (10)	0.0026 (8)	0.0004 (8)	0.0019 (10)
C12	0.0328 (9)	0.0429 (12)	0.0578 (13)	−0.0036 (9)	−0.0041 (10)	0.0024 (11)
C13	0.0415 (11)	0.0409 (11)	0.0590 (13)	0.0028 (10)	−0.0127 (10)	−0.0068 (11)
C14	0.0498 (12)	0.0547 (13)	0.0400 (11)	0.0053 (11)	−0.0068 (10)	−0.0094 (11)
C15	0.0415 (11)	0.0438 (11)	0.0415 (10)	−0.0014 (9)	0.0020 (8)	0.0038 (10)

Geometric parameters (Å, º)

Cl—C11	1.738 (2)	C8—C9	1.300 (3)
O—C7	1.216 (3)	C8—H8A	0.9300
C1—C6	1.388 (3)	C9—C10	1.460 (3)
C1—C2	1.392 (3)	C9—H9A	0.9300
C1—C7	1.489 (3)	C10—C11	1.392 (3)
C2—C3	1.380 (3)	C10—C15	1.398 (3)
C2—H2A	0.9300	C11—C12	1.382 (3)
C3—C4	1.382 (3)	C12—C13	1.377 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.378 (3)	C13—C14	1.379 (3)
C4—H4A	0.9300	C13—H13A	0.9300
C5—C6	1.376 (3)	C14—C15	1.382 (3)
C5—H5A	0.9300	C14—H14A	0.9300
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.479 (3)
C6—C1—C2	118.25 (19)	C7—C8—H8A	118.5
C6—C1—C7	122.84 (18)	C8—C9—C10	127.5 (2)
C2—C1—C7	118.91 (18)	C8—C9—H9A	116.3
C3—C2—C1	120.9 (2)	C10—C9—H9A	116.3
C3—C2—H2A	119.6	C11—C10—C15	116.64 (19)
C1—C2—H2A	119.6	C11—C10—C9	122.17 (19)
C2—C3—C4	119.9 (2)	C15—C10—C9	121.19 (18)
C2—C3—H3A	120.0	C12—C11—C10	122.1 (2)
C4—C3—H3A	120.0	C12—C11—Cl	117.37 (16)
C5—C4—C3	119.8 (2)	C10—C11—Cl	120.50 (16)
C5—C4—H4A	120.1	C13—C12—C11	119.8 (2)
C3—C4—H4A	120.1	C13—C12—H12A	120.1
C6—C5—C4	120.1 (2)	C11—C12—H12A	120.1
C6—C5—H5A	119.9	C12—C13—C14	119.7 (2)
C4—C5—H5A	119.9	C12—C13—H13A	120.1
C5—C6—C1	121.0 (2)	C14—C13—H13A	120.1
C5—C6—H6A	119.5	C13—C14—C15	120.1 (2)
C1—C6—H6A	119.5	C13—C14—H14A	119.9
O—C7—C8	120.35 (18)	C15—C14—H14A	119.9
O—C7—C1	119.84 (18)	C14—C15—C10	121.6 (2)
C8—C7—C1	119.80 (17)	C14—C15—H15A	119.2
C9—C8—C7	123.09 (19)	C10—C15—H15A	119.2
C9—C8—H8A	118.5
C6—C1—C2—C3	−0.1 (3)	C7—C8—C9—C10	179.18 (19)
C7—C1—C2—C3	179.19 (17)	C8—C9—C10—C11	172.1 (2)
C1—C2—C3—C4	−0.3 (3)	C8—C9—C10—C15	−8.8 (3)
C2—C3—C4—C5	0.6 (3)	C15—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	−0.4 (3)	C9—C10—C11—C12	179.46 (19)
C4—C5—C6—C1	−0.1 (3)	C15—C10—C11—Cl	−179.15 (15)
C2—C1—C6—C5	0.3 (3)	C9—C10—C11—Cl	0.0 (3)
C7—C1—C6—C5	−178.96 (18)	C10—C11—C12—C13	−0.1 (3)
C6—C1—C7—O	179.8 (2)	Cl—C11—C12—C13	179.41 (16)
C2—C1—C7—O	0.5 (3)	C11—C12—C13—C14	−0.1 (3)
C6—C1—C7—C8	−0.3 (3)	C12—C13—C14—C15	0.0 (3)
C2—C1—C7—C8	−179.62 (18)	C13—C14—C15—C10	0.3 (3)
O—C7—C8—C9	2.5 (3)	C11—C10—C15—C14	−0.4 (3)
C1—C7—C8—C9	−177.32 (19)	C9—C10—C15—C14	−179.56 (19)