A monoclinic polymorph of 1-(4-chloro-phen-yl)-3-(4-methoxy-phen-yl)prop-2-en-1-one.

The crystal structure of the title compound, C(16)H(13)ClO(2) (II), (space group P2(1)/c,) is a polymorph of the structure, (I), reported by Harrison, Yathirajan, Sarojini, Narayana & Indira [Acta Cryst. (2006), E62, o1647-o1649] in the ortho-rhom-bic space group Pna2(1). The dihedral angle between the mean planes of the 4-chloro- and 4-meth-oxy-substituted benzene rings is 52.9 (1)° in (II) compared to 21.82 (6)° for polymorph (I). The dihedral angles between the mean planes of the prop-2-en-1-one group and those of the 4-chloro-phenyl and 4-methoxy-phenyl rings are 23.3 (3) and 33.7 (1)°, respectively. in (II). The corresponding values are 17.7 (1) and 6.0 (3)°, respectively, in polymorph (I). In the crystal, weak C-H⋯π inter-actions are observed.

Related literature

For the orthorhomic polymorph, see: Harrison et al. (2006 ▶). For the biological activity of chalcones and flavonoids, see: Dimmock et al. (1999 ▶); Opletalova & Sedivy (1999 ▶); Lin et al. (2002 ▶); Nowakowska (2007 ▶). For the synthesis and biological activity of some fluorinated chalcone derivatives, see: Nakamura et al. (2002 ▶). For non-linear optical studies of chalcones and their derivatives, see: Sarojini et al. (2006 ▶); Poornesh et al. (2009 ▶); Shettigar et al. (2006 ▶, 2008 ▶). For our studies of chalcones, see: Jasinski et al. (2009 ▶).

Experimental

Crystal data

C16H13ClO2

M = 272.71

Monoclinic,

a = 15.6695 (7) Å

b = 14.1235 (8) Å

c = 5.8455 (3) Å

β = 90.771 (5)°

V = 1293.53 (12) Å3

Z = 4

Cu Kα radiation

μ = 2.57 mm−1

T = 110 K

0.54 × 0.13 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.483, T max = 0.558

5083 measured reflections

2537 independent reflections

2223 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.04

2537 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054956/om2306sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054956/om2306Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H13ClO2	F(000) = 568
Mr = 272.71	Dx = 1.400 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 3121 reflections
a = 15.6695 (7) Å	θ = 4.2–73.8°
b = 14.1235 (8) Å	µ = 2.57 mm−1
c = 5.8455 (3) Å	T = 110 K
β = 90.771 (5)°	Needle, colorless
V = 1293.53 (12) Å3	0.54 × 0.13 × 0.08 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Ruby (Gemini Cu) detector	2537 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2223 reflections with I > 2σ(I)
graphite	Rint = 0.021
Detector resolution: 10.5081 pixels mm-1	θmax = 74.0°, θmin = 4.2°
ω scans	h = −19→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	k = −16→17
Tmin = 0.483, Tmax = 0.558	l = −5→7
5083 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0574P)2 + 0.4041P] where P = (Fo2 + 2Fc2)/3
2537 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.84683 (2)	0.61936 (3)	0.17788 (6)	0.02523 (13)
O1	0.47093 (7)	0.63259 (9)	0.70069 (19)	0.0289 (3)
O2	0.01821 (7)	0.61488 (8)	−0.07719 (19)	0.0241 (3)
C1	0.57310 (9)	0.62821 (10)	0.4074 (3)	0.0181 (3)
C2	0.63878 (9)	0.66090 (10)	0.5520 (2)	0.0188 (3)
H2	0.6255	0.6849	0.6990	0.023*
C3	0.72286 (9)	0.65859 (10)	0.4828 (3)	0.0198 (3)
H3	0.7672	0.6817	0.5800	0.024*
C4	0.74128 (9)	0.62174 (10)	0.2682 (3)	0.0193 (3)
C5	0.67775 (10)	0.58747 (11)	0.1233 (3)	0.0205 (3)
H5	0.6916	0.5612	−0.0212	0.025*
C6	0.59317 (9)	0.59211 (11)	0.1929 (3)	0.0202 (3)
H6	0.5489	0.5705	0.0934	0.024*
C7	0.48352 (9)	0.63066 (10)	0.4945 (3)	0.0200 (3)
C8	0.41225 (9)	0.63059 (11)	0.3255 (3)	0.0211 (3)
H8	0.4223	0.6467	0.1704	0.025*
C9	0.33359 (9)	0.60773 (11)	0.3930 (3)	0.0200 (3)
H9	0.3284	0.5885	0.5479	0.024*
C10	0.25468 (9)	0.60893 (10)	0.2562 (3)	0.0181 (3)
C11	0.24715 (9)	0.65496 (11)	0.0440 (3)	0.0202 (3)
H11	0.2960	0.6839	−0.0206	0.024*
C12	0.16938 (9)	0.65893 (11)	−0.0730 (3)	0.0200 (3)
H12	0.1648	0.6915	−0.2149	0.024*
C13	0.09809 (9)	0.61476 (10)	0.0193 (3)	0.0187 (3)
C14	0.10492 (9)	0.56679 (11)	0.2274 (3)	0.0202 (3)
H14	0.0567	0.5354	0.2882	0.024*
C15	0.18181 (9)	0.56513 (11)	0.3443 (2)	0.0199 (3)
H15	0.1856	0.5336	0.4877	0.024*
C16	0.00342 (10)	0.67344 (13)	−0.2722 (3)	0.0263 (3)
H16A	0.0140	0.7397	−0.2311	0.039*
H16B	−0.0559	0.6662	−0.3248	0.039*
H16C	0.0420	0.6547	−0.3948	0.039*

	U11	U22	U33	U12	U13	U23
Cl1	0.0180 (2)	0.0276 (2)	0.0302 (2)	0.00214 (13)	0.00556 (14)	0.00128 (15)
O1	0.0214 (6)	0.0441 (7)	0.0212 (6)	−0.0035 (5)	0.0006 (4)	0.0008 (5)
O2	0.0158 (5)	0.0266 (6)	0.0298 (6)	−0.0025 (4)	−0.0041 (4)	0.0048 (5)
C1	0.0174 (7)	0.0170 (7)	0.0198 (7)	−0.0009 (5)	−0.0019 (5)	0.0039 (6)
C2	0.0197 (7)	0.0188 (7)	0.0180 (7)	0.0019 (5)	−0.0009 (5)	−0.0002 (6)
C3	0.0185 (7)	0.0188 (7)	0.0221 (7)	0.0000 (5)	−0.0031 (5)	−0.0009 (6)
C4	0.0167 (7)	0.0172 (7)	0.0239 (7)	0.0018 (5)	0.0022 (6)	0.0034 (6)
C5	0.0251 (7)	0.0189 (7)	0.0176 (7)	0.0019 (6)	0.0016 (6)	−0.0002 (5)
C6	0.0194 (7)	0.0206 (7)	0.0206 (7)	−0.0015 (5)	−0.0038 (5)	0.0008 (6)
C7	0.0196 (7)	0.0193 (7)	0.0212 (7)	−0.0006 (5)	−0.0008 (6)	0.0012 (6)
C8	0.0178 (7)	0.0248 (8)	0.0207 (7)	0.0005 (6)	0.0000 (6)	0.0021 (6)
C9	0.0206 (7)	0.0189 (7)	0.0204 (7)	0.0017 (5)	−0.0001 (6)	0.0010 (6)
C10	0.0167 (7)	0.0170 (7)	0.0207 (7)	0.0023 (5)	0.0015 (5)	−0.0012 (6)
C11	0.0164 (7)	0.0222 (7)	0.0220 (7)	−0.0007 (5)	0.0032 (5)	0.0011 (6)
C12	0.0195 (7)	0.0215 (8)	0.0190 (7)	0.0001 (6)	0.0012 (5)	0.0008 (6)
C13	0.0161 (7)	0.0171 (7)	0.0228 (7)	0.0009 (5)	−0.0013 (5)	−0.0033 (6)
C14	0.0177 (7)	0.0187 (7)	0.0245 (7)	−0.0015 (5)	0.0039 (5)	0.0012 (6)
C15	0.0212 (7)	0.0186 (7)	0.0201 (7)	0.0016 (6)	0.0030 (5)	0.0015 (6)
C16	0.0213 (7)	0.0341 (9)	0.0235 (8)	0.0027 (6)	−0.0036 (6)	0.0014 (7)

Cl1—C4	1.7431 (15)	C8—H8	0.9500
O1—C7	1.2240 (19)	C9—C10	1.464 (2)
O2—C13	1.3659 (18)	C9—H9	0.9500
O2—C16	1.4248 (19)	C10—C15	1.403 (2)
C1—C6	1.394 (2)	C10—C11	1.404 (2)
C1—C2	1.401 (2)	C11—C12	1.391 (2)
C1—C7	1.500 (2)	C11—H11	0.9500
C2—C3	1.384 (2)	C12—C13	1.395 (2)
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.392 (2)	C13—C14	1.395 (2)
C3—H3	0.9500	C14—C15	1.377 (2)
C4—C5	1.386 (2)	C14—H14	0.9500
C5—C6	1.393 (2)	C15—H15	0.9500
C5—H5	0.9500	C16—H16A	0.9800
C6—H6	0.9500	C16—H16B	0.9800
C7—C8	1.481 (2)	C16—H16C	0.9800
C8—C9	1.339 (2)
C13—O2—C16	118.00 (12)	C8—C9—H9	116.2
C6—C1—C2	119.36 (14)	C10—C9—H9	116.2
C6—C1—C7	122.52 (13)	C15—C10—C11	118.00 (13)
C2—C1—C7	118.09 (13)	C15—C10—C9	118.70 (14)
C3—C2—C1	120.69 (14)	C11—C10—C9	123.25 (13)
C3—C2—H2	119.7	C12—C11—C10	121.06 (13)
C1—C2—H2	119.7	C12—C11—H11	119.5
C2—C3—C4	118.82 (13)	C10—C11—H11	119.5
C2—C3—H3	120.6	C11—C12—C13	119.52 (14)
C4—C3—H3	120.6	C11—C12—H12	120.2
C5—C4—C3	121.70 (14)	C13—C12—H12	120.2
C5—C4—Cl1	119.01 (12)	O2—C13—C12	125.02 (13)
C3—C4—Cl1	119.29 (11)	O2—C13—C14	114.83 (13)
C4—C5—C6	118.91 (14)	C12—C13—C14	120.15 (13)
C4—C5—H5	120.5	C15—C14—C13	119.82 (14)
C6—C5—H5	120.5	C15—C14—H14	120.1
C5—C6—C1	120.48 (13)	C13—C14—H14	120.1
C5—C6—H6	119.8	C14—C15—C10	121.41 (14)
C1—C6—H6	119.8	C14—C15—H15	119.3
O1—C7—C8	121.77 (14)	C10—C15—H15	119.3
O1—C7—C1	119.92 (13)	O2—C16—H16A	109.5
C8—C7—C1	118.31 (13)	O2—C16—H16B	109.5
C9—C8—C7	119.51 (14)	H16A—C16—H16B	109.5
C9—C8—H8	120.2	O2—C16—H16C	109.5
C7—C8—H8	120.2	H16A—C16—H16C	109.5
C8—C9—C10	127.64 (14)	H16B—C16—H16C	109.5
C6—C1—C2—C3	0.7 (2)	C7—C8—C9—C10	176.11 (14)
C7—C1—C2—C3	178.69 (13)	C8—C9—C10—C15	167.66 (15)
C1—C2—C3—C4	−1.0 (2)	C8—C9—C10—C11	−14.8 (2)
C2—C3—C4—C5	−0.1 (2)	C15—C10—C11—C12	1.4 (2)
C2—C3—C4—Cl1	179.45 (11)	C9—C10—C11—C12	−176.08 (14)
C3—C4—C5—C6	1.4 (2)	C10—C11—C12—C13	−1.4 (2)
Cl1—C4—C5—C6	−178.06 (11)	C16—O2—C13—C12	−7.9 (2)
C4—C5—C6—C1	−1.8 (2)	C16—O2—C13—C14	171.26 (13)
C2—C1—C6—C5	0.7 (2)	C11—C12—C13—O2	178.95 (14)
C7—C1—C6—C5	−177.17 (14)	C11—C12—C13—C14	−0.2 (2)
C6—C1—C7—O1	155.92 (15)	O2—C13—C14—C15	−177.58 (13)
C2—C1—C7—O1	−22.0 (2)	C12—C13—C14—C15	1.6 (2)
C6—C1—C7—C8	−24.0 (2)	C13—C14—C15—C10	−1.6 (2)
C2—C1—C7—C8	158.05 (14)	C11—C10—C15—C14	0.0 (2)
O1—C7—C8—C9	−17.5 (2)	C9—C10—C15—C14	177.68 (13)
C1—C7—C8—C9	162.41 (14)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1	0.95	2.47	2.8080 (19)	101
C2—H2···Cg1i	0.95	2.85	3.4675 (15)	124
C12—H12···Cg2ii	0.95	2.92	3.6616 (17)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg1i	0.95	2.85	3.4675 (15)	124
C12—H12⋯Cg2ii	0.95	2.92	3.6616 (17)	136

Symmetry codes: (i) ; (ii) .