6-Chloro-4-(2-phenyl-ethen-yl)chroman-2-one.

The title compound, C(17)H(13)ClO(2), was obtained from the oxidation of 6-chloro-4-(2-phenyl-ethen-yl)chroman-2-ol, which was synthesized by the reaction of of (E)-3-(5-chloro-2-hy-droxy-phen-yl)acryl-aldehyde with styrylboronic acid using diethyl-amine as a catalyst. The six-membered pyran-one ring of the chromane system has a screw-boat conformation. The dihedral angle between the least-squares planes of the chromane ring system and the styryl group is 85.28 (9)°.

Related literature

For the synthesis of the title compound, see: Choi & Kim (2010 ▶). For the biological activity of chromenes, see: Ellis & Lockhart (2007 ▶); Green et al. (1996) ▶; Horton et al. (2003 ▶).

Experimental

Crystal data

C17H13ClO2

M = 284.72

Monoclinic,

a = 15.6682 (3) Å

b = 6.2800 (1) Å

c = 14.9383 (3) Å

β = 115.129 (1)°

V = 1330.76 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 100 K

0.28 × 0.13 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.925, T max = 0.986

12258 measured reflections

3325 independent reflections

2839 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.083

S = 1.06

3325 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045101/is2627sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045101/is2627Isup2.hkl

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

C17H13ClO2	F(000) = 592
Mr = 284.72	Dx = 1.421 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5561 reflections
a = 15.6682 (3) Å	θ = 3.6–28.3°
b = 6.2800 (1) Å	µ = 0.28 mm−1
c = 14.9383 (3) Å	T = 100 K
β = 115.129 (1)°	Block, silver
V = 1330.76 (4) Å3	0.28 × 0.13 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	3325 independent reflections
Radiation source: fine-focus sealed tube	2839 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 28.4°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→20
Tmin = 0.925, Tmax = 0.986	k = −8→8
12258 measured reflections	l = −19→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0306P)2 + 0.755P] where P = (Fo2 + 2Fc2)/3
3325 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.37 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	0.64583 (2)	0.83763 (5)	0.61691 (2)	0.02134 (9)
O1	0.35931 (6)	0.24736 (14)	0.62698 (7)	0.0185 (2)
O2	0.21611 (7)	0.17409 (16)	0.60995 (8)	0.0267 (2)
C1	0.39949 (9)	0.6045 (2)	0.59464 (9)	0.0149 (2)
C2	0.42529 (9)	0.3975 (2)	0.62766 (9)	0.0156 (2)
C3	0.51713 (9)	0.3250 (2)	0.65950 (9)	0.0176 (3)
H3A	0.5325	0.1864	0.6827	0.021*
C4	0.58581 (9)	0.4603 (2)	0.65657 (9)	0.0186 (3)
H4A	0.6477	0.4141	0.6777	0.022*
C5	0.56024 (9)	0.6657 (2)	0.62152 (9)	0.0166 (3)
C6	0.46877 (9)	0.7392 (2)	0.59102 (9)	0.0161 (2)
H6A	0.4536	0.8781	0.5682	0.019*
C7	0.27232 (9)	0.3112 (2)	0.61886 (10)	0.0186 (3)
C8	0.25822 (9)	0.5461 (2)	0.62445 (10)	0.0181 (3)
H8A	0.2881	0.5907	0.6931	0.022*
H8B	0.1913	0.5753	0.5998	0.022*
C9	0.29900 (9)	0.6771 (2)	0.56459 (9)	0.0158 (2)
H9A	0.2998	0.8275	0.5824	0.019*
C10	0.24087 (9)	0.6545 (2)	0.45496 (9)	0.0163 (2)
H10A	0.2362	0.5208	0.4265	0.020*
C11	0.19575 (9)	0.8170 (2)	0.39674 (10)	0.0170 (3)
H11A	0.2035	0.9496	0.4269	0.020*
C12	0.13500 (9)	0.8094 (2)	0.28984 (9)	0.0158 (2)
C13	0.07977 (9)	0.9877 (2)	0.24476 (10)	0.0189 (3)
H13A	0.0856	1.1106	0.2816	0.023*
C14	0.01637 (9)	0.9834 (2)	0.14573 (10)	0.0213 (3)
H14A	−0.0200	1.1029	0.1169	0.026*
C15	0.00700 (9)	0.8019 (2)	0.08960 (10)	0.0209 (3)
H15A	−0.0367	0.7976	0.0238	0.025*
C16	0.06374 (9)	0.6256 (2)	0.13271 (10)	0.0202 (3)
H16A	0.0591	0.5048	0.0949	0.024*
C17	0.12697 (9)	0.6293 (2)	0.23151 (10)	0.0184 (3)
H17A	0.1645	0.5109	0.2594	0.022*

	U11	U22	U33	U12	U13	U23
Cl1	0.01884 (16)	0.02132 (17)	0.02491 (18)	−0.00529 (12)	0.01029 (13)	−0.00125 (13)
O1	0.0182 (4)	0.0133 (4)	0.0248 (5)	−0.0015 (4)	0.0099 (4)	0.0013 (4)
O2	0.0231 (5)	0.0219 (5)	0.0368 (6)	−0.0055 (4)	0.0142 (5)	0.0006 (4)
C1	0.0160 (6)	0.0155 (6)	0.0117 (6)	0.0004 (5)	0.0044 (5)	−0.0005 (5)
C2	0.0172 (6)	0.0153 (6)	0.0138 (6)	−0.0027 (5)	0.0062 (5)	−0.0011 (5)
C3	0.0196 (6)	0.0145 (6)	0.0169 (6)	0.0023 (5)	0.0061 (5)	0.0020 (5)
C4	0.0156 (6)	0.0203 (6)	0.0180 (6)	0.0011 (5)	0.0053 (5)	−0.0005 (5)
C5	0.0173 (6)	0.0174 (6)	0.0156 (6)	−0.0044 (5)	0.0073 (5)	−0.0019 (5)
C6	0.0198 (6)	0.0136 (6)	0.0138 (6)	−0.0009 (5)	0.0060 (5)	0.0000 (5)
C7	0.0188 (6)	0.0209 (7)	0.0168 (6)	−0.0015 (5)	0.0081 (5)	0.0003 (5)
C8	0.0177 (6)	0.0191 (6)	0.0187 (6)	0.0002 (5)	0.0087 (5)	−0.0008 (5)
C9	0.0160 (6)	0.0134 (6)	0.0169 (6)	0.0003 (5)	0.0059 (5)	−0.0006 (5)
C10	0.0154 (6)	0.0153 (6)	0.0176 (6)	−0.0010 (5)	0.0064 (5)	−0.0020 (5)
C11	0.0160 (6)	0.0166 (6)	0.0195 (6)	−0.0009 (5)	0.0087 (5)	−0.0008 (5)
C12	0.0137 (5)	0.0173 (6)	0.0173 (6)	−0.0005 (5)	0.0076 (5)	0.0027 (5)
C13	0.0211 (6)	0.0175 (6)	0.0214 (7)	0.0022 (5)	0.0123 (5)	0.0013 (5)
C14	0.0206 (6)	0.0235 (7)	0.0218 (7)	0.0074 (5)	0.0110 (5)	0.0069 (5)
C15	0.0170 (6)	0.0297 (7)	0.0158 (6)	0.0015 (5)	0.0067 (5)	0.0029 (5)
C16	0.0200 (6)	0.0216 (7)	0.0201 (7)	−0.0018 (5)	0.0096 (5)	−0.0031 (5)
C17	0.0176 (6)	0.0167 (6)	0.0217 (7)	0.0031 (5)	0.0092 (5)	0.0030 (5)

Cl1—C5	1.7456 (13)	C9—C10	1.5049 (17)
O1—C7	1.3758 (15)	C9—H9A	0.9800
O1—C2	1.3962 (15)	C10—C11	1.3322 (18)
O2—C7	1.1981 (16)	C10—H10A	0.9300
C1—C2	1.3880 (18)	C11—C12	1.4722 (18)
C1—C6	1.3953 (17)	C11—H11A	0.9300
C1—C9	1.5127 (17)	C12—C13	1.4002 (18)
C2—C3	1.3867 (18)	C12—C17	1.4004 (18)
C3—C4	1.3863 (18)	C13—C14	1.3884 (19)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.3861 (19)	C14—C15	1.385 (2)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.3856 (18)	C15—C16	1.3945 (19)
C6—H6A	0.9300	C15—H15A	0.9300
C7—C8	1.4990 (19)	C16—C17	1.3851 (19)
C8—C9	1.5394 (17)	C16—H16A	0.9300
C8—H8A	0.9700	C17—H17A	0.9300
C8—H8B	0.9700
C7—O1—C2	120.43 (10)	C10—C9—C8	111.91 (10)
C2—C1—C6	117.87 (11)	C1—C9—C8	107.64 (10)
C2—C1—C9	119.80 (11)	C10—C9—H9A	108.6
C6—C1—C9	122.32 (11)	C1—C9—H9A	108.6
C3—C2—C1	122.19 (12)	C8—C9—H9A	108.6
C3—C2—O1	115.96 (11)	C11—C10—C9	123.12 (12)
C1—C2—O1	121.80 (11)	C11—C10—H10A	118.4
C4—C3—C2	119.62 (12)	C9—C10—H10A	118.4
C4—C3—H3A	120.2	C10—C11—C12	127.08 (12)
C2—C3—H3A	120.2	C10—C11—H11A	116.5
C5—C4—C3	118.59 (12)	C12—C11—H11A	116.5
C5—C4—H4A	120.7	C13—C12—C17	118.20 (12)
C3—C4—H4A	120.7	C13—C12—C11	118.61 (12)
C6—C5—C4	121.80 (12)	C17—C12—C11	123.15 (12)
C6—C5—Cl1	119.05 (10)	C14—C13—C12	120.90 (12)
C4—C5—Cl1	119.14 (10)	C14—C13—H13A	119.6
C5—C6—C1	119.89 (12)	C12—C13—H13A	119.6
C5—C6—H6A	120.1	C15—C14—C13	120.31 (13)
C1—C6—H6A	120.1	C15—C14—H14A	119.8
O2—C7—O1	117.02 (12)	C13—C14—H14A	119.8
O2—C7—C8	126.49 (12)	C14—C15—C16	119.39 (13)
O1—C7—C8	116.47 (11)	C14—C15—H15A	120.3
C7—C8—C9	112.71 (10)	C16—C15—H15A	120.3
C7—C8—H8A	109.0	C17—C16—C15	120.39 (12)
C9—C8—H8A	109.0	C17—C16—H16A	119.8
C7—C8—H8B	109.0	C15—C16—H16A	119.8
C9—C8—H8B	109.0	C16—C17—C12	120.75 (12)
H8A—C8—H8B	107.8	C16—C17—H17A	119.6
C10—C9—C1	111.54 (10)	C12—C17—H17A	119.6
C6—C1—C2—C3	2.07 (19)	C2—C1—C9—C10	−94.72 (14)
C9—C1—C2—C3	−177.61 (12)	C6—C1—C9—C10	85.61 (14)
C6—C1—C2—O1	−175.28 (11)	C2—C1—C9—C8	28.41 (15)
C9—C1—C2—O1	5.04 (18)	C6—C1—C9—C8	−151.26 (12)
C7—O1—C2—C3	165.08 (11)	C7—C8—C9—C10	72.17 (14)
C7—O1—C2—C1	−17.41 (17)	C7—C8—C9—C1	−50.73 (14)
C1—C2—C3—C4	−1.5 (2)	C1—C9—C10—C11	−122.70 (13)
O1—C2—C3—C4	175.98 (11)	C8—C9—C10—C11	116.65 (13)
C2—C3—C4—C5	−0.02 (19)	C9—C10—C11—C12	−177.86 (11)
C3—C4—C5—C6	0.96 (19)	C10—C11—C12—C13	168.28 (12)
C3—C4—C5—Cl1	−179.75 (10)	C10—C11—C12—C17	−9.2 (2)
C4—C5—C6—C1	−0.38 (19)	C17—C12—C13—C14	2.21 (18)
Cl1—C5—C6—C1	−179.67 (9)	C11—C12—C13—C14	−175.41 (11)
C2—C1—C6—C5	−1.11 (18)	C12—C13—C14—C15	−0.25 (19)
C9—C1—C6—C5	178.56 (11)	C13—C14—C15—C16	−1.82 (19)
C2—O1—C7—O2	173.59 (12)	C14—C15—C16—C17	1.90 (19)
C2—O1—C7—C8	−7.79 (17)	C15—C16—C17—C12	0.10 (19)
O2—C7—C8—C9	−138.65 (14)	C13—C12—C17—C16	−2.13 (18)
O1—C7—C8—C9	42.87 (16)	C11—C12—C17—C16	175.38 (12)