2-(4-Chloro-phen-yl)chromen-4-one.

The title compound, C(15)H(9)ClO(2), is a synthetic flavonoid obtained by the cyclization of 3-(4-chloro-phen-yl)-1-(2-hy-droxy-phen-yl)prop-2-en-1-one. The 4-chloro-phenyl ring is twisted at an angle of 11.54° with respect to the chromen-4-one skeleton. In the crystal, pairs of mol-ecules are inter-connected by weak Cl⋯Cl inter-actions [3.3089 (10) Å] forming dimmers which are further peripherally connected through inter-molecular C-H⋯O hydrogen bonds.

Related literature

For general features and crystal structures of flavanoids, see: Tim Cushnie & Lamb (2005 ▶); Wera et al. (2011 ▶). For crystal structures of small mol­ecules, see: Singh, Agarwal & Awasthi (2011 ▶); Singh, Singh et al. (2011 ▶). For the synthesis, see: Migrdichian (1957 ▶); Awasthi et al. (2009 ▶); Shah et al. (1955 ▶). For inter­molecular inter­actions and bond lengths and angles, see: Reddy et al. (2006 ▶); Wang et al. (2010 ▶); Desiraju & Steiner (1999 ▶); Waller et al. (2003 ▶); Allen et al. (1987 ▶).

Experimental

Crystal data

C15H9ClO2

M = 256.67

Monoclinic,

a = 22.1564 (16) Å

b = 3.8745 (2) Å

c = 26.7728 (18) Å

β = 95.524 (6)°

V = 2287.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.40 × 0.39 × 0.38 mm

Data collection

Oxford Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.938, T max = 0.941

8152 measured reflections

2249 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.037

Standard reflections: 0

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.119

S = 1.10

2249 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043832/zj2023sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043832/zj2023Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043832/zj2023Isup3.cml

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

C15H9ClO2	F(000) = 528
Mr = 256.67	Dx = 1.490 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3949 reflections
a = 22.1564 (16) Å	θ = 3.1–32.6°
b = 3.8745 (2) Å	µ = 0.32 mm−1
c = 26.7728 (18) Å	T = 293 K
β = 95.524 (6)°	Needle, colourless
V = 2287.6 (3) Å3	0.40 × 0.39 × 0.38 mm
Z = 8

Oxford Xcalibur Eos diffractometer	2249 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 26.0°, θmin = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −26→26
Tmin = 0.938, Tmax = 0.941	k = −4→4
8152 measured reflections	l = −33→33

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0483P)2 + 1.836P] where P = (Fo2 + 2Fc2)/3
2249 reflections	(Δ/σ)max = 0.009
163 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.24 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	0.31934 (3)	0.85487 (18)	0.02358 (2)	0.0570 (2)
C9	0.53822 (9)	1.4266 (6)	0.14239 (7)	0.0337 (5)
C6	0.64493 (9)	1.7175 (6)	0.18541 (7)	0.0354 (5)
C10	0.48486 (9)	1.2780 (6)	0.11311 (7)	0.0337 (5)
C1	0.63679 (9)	1.6341 (5)	0.13486 (7)	0.0339 (5)
C13	0.38335 (9)	1.0144 (6)	0.05827 (8)	0.0397 (5)
C15	0.48053 (10)	1.2743 (6)	0.06106 (8)	0.0400 (5)
H15	0.5123	1.3606	0.0445	0.048*
C8	0.54262 (10)	1.5012 (7)	0.19128 (8)	0.0461 (6)
H8	0.5095	1.4573	0.2092	0.055*
C5	0.70028 (10)	1.8653 (6)	0.20370 (8)	0.0428 (5)
H5	0.7069	1.9248	0.2374	0.051*
C2	0.68118 (10)	1.6940 (6)	0.10315 (8)	0.0431 (5)
H2	0.6748	1.6370	0.0693	0.052*
C14	0.42994 (10)	1.1448 (6)	0.03366 (8)	0.0436 (6)
H14	0.4273	1.1455	−0.0012	0.052*
C11	0.43729 (10)	1.1410 (6)	0.13715 (8)	0.0416 (5)
H11	0.4397	1.1385	0.1720	0.050*
C12	0.38674 (10)	1.0092 (6)	0.10974 (8)	0.0431 (5)
H12	0.3551	0.9172	0.1260	0.052*
C7	0.59653 (11)	1.6468 (6)	0.21751 (8)	0.0445 (6)
O2	0.60167 (9)	1.7078 (6)	0.26277 (6)	0.0690 (6)
C3	0.73488 (10)	1.8388 (6)	0.12232 (9)	0.0472 (6)
H3	0.7651	1.8809	0.1013	0.057*
C4	0.74463 (11)	1.9233 (6)	0.17286 (9)	0.0475 (6)
H4	0.7814	2.0193	0.1856	0.057*
O1	0.58414 (6)	1.4868 (4)	0.11337 (5)	0.0382 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0454 (4)	0.0656 (5)	0.0582 (4)	−0.0157 (3)	−0.0049 (3)	−0.0043 (3)
C9	0.0323 (10)	0.0380 (12)	0.0317 (10)	0.0045 (9)	0.0076 (8)	0.0045 (9)
C6	0.0365 (11)	0.0363 (12)	0.0332 (11)	0.0054 (9)	0.0013 (9)	0.0023 (9)
C10	0.0323 (11)	0.0353 (11)	0.0337 (10)	0.0045 (9)	0.0033 (8)	0.0035 (9)
C1	0.0319 (10)	0.0358 (12)	0.0336 (10)	0.0005 (9)	0.0011 (8)	0.0027 (9)
C13	0.0326 (11)	0.0390 (12)	0.0466 (12)	−0.0030 (10)	−0.0011 (9)	−0.0010 (10)
C15	0.0375 (11)	0.0492 (13)	0.0342 (11)	−0.0041 (10)	0.0082 (9)	0.0025 (10)
C8	0.0389 (12)	0.0672 (16)	0.0331 (11)	−0.0059 (11)	0.0085 (9)	0.0006 (11)
C5	0.0437 (12)	0.0432 (13)	0.0398 (12)	0.0003 (11)	−0.0045 (10)	−0.0018 (10)
C2	0.0408 (12)	0.0529 (14)	0.0361 (11)	−0.0015 (11)	0.0060 (9)	−0.0002 (10)
C14	0.0444 (13)	0.0533 (15)	0.0331 (11)	−0.0050 (11)	0.0038 (10)	−0.0002 (10)
C11	0.0393 (12)	0.0529 (14)	0.0334 (11)	−0.0009 (11)	0.0076 (9)	0.0040 (10)
C12	0.0347 (11)	0.0496 (14)	0.0461 (12)	−0.0054 (10)	0.0103 (10)	0.0052 (11)
C7	0.0451 (13)	0.0563 (15)	0.0321 (11)	0.0007 (12)	0.0038 (9)	−0.0031 (10)
O2	0.0648 (12)	0.1114 (17)	0.0314 (9)	−0.0159 (11)	0.0068 (8)	−0.0149 (10)
C3	0.0379 (12)	0.0508 (15)	0.0539 (14)	−0.0036 (11)	0.0105 (10)	0.0053 (12)
C4	0.0382 (12)	0.0450 (14)	0.0574 (14)	−0.0045 (11)	−0.0045 (11)	0.0018 (12)
O1	0.0326 (7)	0.0541 (10)	0.0282 (7)	−0.0041 (7)	0.0045 (6)	−0.0028 (7)

Cl1—C13	1.733 (2)	C8—C7	1.441 (3)
C9—C8	1.335 (3)	C8—H8	0.9300
C9—O1	1.358 (2)	C5—C4	1.362 (3)
C9—C10	1.471 (3)	C5—H5	0.9300
C6—C1	1.386 (3)	C2—C3	1.370 (3)
C6—C5	1.399 (3)	C2—H2	0.9300
C6—C7	1.463 (3)	C14—H14	0.9300
C10—C15	1.388 (3)	C11—C12	1.377 (3)
C10—C11	1.392 (3)	C11—H11	0.9300
C1—O1	1.374 (2)	C12—H12	0.9300
C1—C2	1.379 (3)	C7—O2	1.229 (3)
C13—C14	1.373 (3)	C3—C4	1.389 (3)
C13—C12	1.373 (3)	C3—H3	0.9300
C15—C14	1.374 (3)	C4—H4	0.9300
C15—H15	0.9300
C8—C9—O1	122.4 (2)	C6—C5—H5	119.5
C8—C9—C10	125.9 (2)	C3—C2—C1	118.9 (2)
O1—C9—C10	111.72 (17)	C3—C2—H2	120.5
C1—C6—C5	117.7 (2)	C1—C2—H2	120.5
C1—C6—C7	119.74 (19)	C13—C14—C15	119.4 (2)
C5—C6—C7	122.57 (19)	C13—C14—H14	120.3
C15—C10—C11	118.6 (2)	C15—C14—H14	120.3
C15—C10—C9	120.89 (19)	C12—C11—C10	120.5 (2)
C11—C10—C9	120.54 (18)	C12—C11—H11	119.7
O1—C1—C2	116.05 (18)	C10—C11—H11	119.7
O1—C1—C6	122.07 (18)	C13—C12—C11	119.5 (2)
C2—C1—C6	121.9 (2)	C13—C12—H12	120.2
C14—C13—C12	121.1 (2)	C11—C12—H12	120.2
C14—C13—Cl1	119.24 (17)	O2—C7—C8	123.3 (2)
C12—C13—Cl1	119.70 (17)	O2—C7—C6	122.7 (2)
C14—C15—C10	120.9 (2)	C8—C7—C6	114.01 (18)
C14—C15—H15	119.5	C2—C3—C4	120.6 (2)
C10—C15—H15	119.5	C2—C3—H3	119.7
C9—C8—C7	122.8 (2)	C4—C3—H3	119.7
C9—C8—H8	118.6	C5—C4—C3	119.9 (2)
C7—C8—H8	118.6	C5—C4—H4	120.1
C4—C5—C6	121.0 (2)	C3—C4—H4	120.1
C4—C5—H5	119.5	C9—O1—C1	118.96 (15)
C8—C9—C10—C15	167.0 (2)	C15—C10—C11—C12	−0.9 (3)
O1—C9—C10—C15	−12.2 (3)	C9—C10—C11—C12	178.5 (2)
C8—C9—C10—C11	−12.3 (4)	C14—C13—C12—C11	0.9 (4)
O1—C9—C10—C11	168.48 (19)	Cl1—C13—C12—C11	−179.02 (18)
C5—C6—C1—O1	179.74 (19)	C10—C11—C12—C13	−0.2 (4)
C7—C6—C1—O1	0.3 (3)	C9—C8—C7—O2	−178.0 (3)
C5—C6—C1—C2	−0.2 (3)	C9—C8—C7—C6	2.2 (4)
C7—C6—C1—C2	−179.6 (2)	C1—C6—C7—O2	178.3 (2)
C11—C10—C15—C14	1.3 (4)	C5—C6—C7—O2	−1.1 (4)
C9—C10—C15—C14	−178.1 (2)	C1—C6—C7—C8	−1.9 (3)
O1—C9—C8—C7	−0.9 (4)	C5—C6—C7—C8	178.7 (2)
C10—C9—C8—C7	180.0 (2)	C1—C2—C3—C4	0.2 (4)
C1—C6—C5—C4	−0.3 (3)	C6—C5—C4—C3	0.7 (4)
C7—C6—C5—C4	179.1 (2)	C2—C3—C4—C5	−0.7 (4)
O1—C1—C2—C3	−179.7 (2)	C8—C9—O1—C1	−0.9 (3)
C6—C1—C2—C3	0.3 (3)	C10—C9—O1—C1	178.32 (17)
C12—C13—C14—C15	−0.5 (4)	C2—C1—O1—C9	−178.86 (19)
Cl1—C13—C14—C15	179.43 (18)	C6—C1—O1—C9	1.2 (3)
C10—C15—C14—C13	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O2i	0.93	2.64	3.345 (3)	134.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O2i	0.93	2.64	3.345 (3)	134 (1)

Symmetry code: (i) .