2-(3-Chloro­phenyl)­chroman-4-one

The title compound, C₁₅H₁₁ClO₂, was synthesized from 3-(3-chloro­phenyl)-1-(2-hydroxy­phenyl)­prop-2-en-1-one. The pyrone ring adopts a half-chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 292 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.037
• wR factor = 0.083
• Data-to-parameter ratio = 14.0

checkCIF/PLATON results

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2-(3-Chlorophenyl)chroman-4-one

Crystal data

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.396 Mg m^−3
Monoclinic, P21/n	Melting point = 360–362 K
Hall symbol: -P2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.979 (2) Å	Cell parameters from 30 reflections
b = 5.202 (1) Å	θ = 3.4–12.4°
c = 19.773 (3) Å	µ = 0.30 mm^−1
β = 92.22 (2)°	T = 292 K
V = 1231.1 (4) Å^3	Block, colorless
Z = 4	0.52 × 0.42 × 0.42 mm

Data collection

Siemens P4 diffractometer	1314 reflections with I > 2σ(I)
Radiation source: normal-focus sealed	Rint = 0.018
Graphite monochromator	θmax = 25.5°, θmin = 2.0°
ω scans	h = 0→14
Absorption correction: multi-scan (SHELXTL; Sheldrick, 1997)	k = 0→6
Tmin = 0.853, Tmax = 0.882	l = −23→23
2790 measured reflections	3 standard reflections every 97 reflections
2296 independent reflections	intensity decay: 1.8%

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)] = 0.037	H-atom parameters constrained
wR(F^2) = 0.083	w = 1/[σ^2(Fo^2) + (0.0361P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
2296 reflections	Δρmax = 0.14 e Å^−3
164 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0140 (14)

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	0.37521 (6)	0.76472 (16)	0.76397 (3)	0.0895 (3)
O1	0.30778 (10)	0.5874 (3)	0.45815 (6)	0.0463 (4)
O2	−0.02981 (11)	0.6705 (3)	0.42597 (7)	0.0590 (5)
C1	0.25295 (16)	0.4486 (4)	0.40849 (9)	0.0416 (5)
C2	0.31691 (18)	0.2908 (4)	0.36892 (10)	0.0537 (6)
H2	0.3943	0.2888	0.3749	0.064*
C3	0.2652 (2)	0.1376 (5)	0.32083 (10)	0.0612 (7)
H3	0.3082	0.0331	0.2940	0.073*
C4	0.1494 (2)	0.1353 (5)	0.31143 (10)	0.0598 (6)
H4	0.1152	0.0259	0.2797	0.072*
C5	0.08711 (18)	0.2948 (4)	0.34908 (9)	0.0511 (6)
H5	0.0099	0.2957	0.3422	0.061*
C6	0.13659 (16)	0.4578 (4)	0.39800 (9)	0.0405 (5)
C7	0.07052 (17)	0.6424 (4)	0.43605 (9)	0.0440 (5)
C8	0.13663 (15)	0.7996 (4)	0.48742 (10)	0.0467 (5)
H8A	0.0898	0.8421	0.5248	0.056*
H8B	0.1598	0.9591	0.4668	0.056*
C9	0.23826 (15)	0.6549 (4)	0.51392 (9)	0.0416 (5)
H9	0.2132	0.4957	0.5351	0.050*
C10	0.30868 (15)	0.8012 (4)	0.56514 (9)	0.0416 (5)
C11	0.37189 (17)	1.0108 (4)	0.54672 (10)	0.0523 (6)
H11	0.3726	1.0600	0.5015	0.063*
C12	0.43391 (18)	1.1473 (5)	0.59483 (12)	0.0615 (7)
H12	0.4762	1.2878	0.5820	0.074*
C13	0.43318 (18)	1.0750 (5)	0.66220 (12)	0.0640 (7)
H13	0.4740	1.1672	0.6950	0.077*
C14	0.37154 (18)	0.8661 (5)	0.67979 (10)	0.0552 (6)
C15	0.30882 (16)	0.7294 (4)	0.63240 (9)	0.0483 (5)
H15	0.2667	0.5892	0.6456	0.058*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.1018 (5)	0.1186 (7)	0.0470 (3)	0.0120 (5)	−0.0134 (3)	−0.0101 (4)
O1	0.0378 (8)	0.0548 (9)	0.0467 (8)	−0.0013 (7)	0.0071 (6)	−0.0104 (7)
O2	0.0413 (8)	0.0773 (12)	0.0581 (9)	0.0091 (9)	−0.0039 (7)	−0.0033 (8)
C1	0.0459 (13)	0.0400 (13)	0.0388 (11)	0.0000 (11)	0.0018 (9)	0.0017 (10)
C2	0.0522 (13)	0.0604 (15)	0.0491 (12)	0.0066 (13)	0.0085 (11)	−0.0058 (12)
C3	0.0780 (18)	0.0582 (16)	0.0481 (13)	0.0127 (14)	0.0097 (12)	−0.0089 (12)
C4	0.0772 (17)	0.0582 (16)	0.0433 (12)	−0.0010 (14)	−0.0072 (12)	−0.0081 (12)
C5	0.0563 (13)	0.0558 (15)	0.0404 (11)	0.0001 (13)	−0.0064 (10)	0.0030 (12)
C6	0.0442 (12)	0.0409 (12)	0.0362 (10)	0.0021 (11)	−0.0015 (9)	0.0067 (10)
C7	0.0451 (13)	0.0474 (13)	0.0397 (11)	0.0029 (11)	0.0027 (10)	0.0093 (10)
C8	0.0444 (12)	0.0444 (13)	0.0512 (11)	0.0049 (11)	0.0013 (10)	−0.0031 (11)
C9	0.0388 (11)	0.0448 (13)	0.0414 (11)	0.0028 (10)	0.0029 (9)	−0.0013 (10)
C10	0.0366 (11)	0.0436 (13)	0.0447 (11)	0.0053 (11)	0.0029 (9)	−0.0034 (10)
C11	0.0495 (13)	0.0527 (15)	0.0546 (13)	0.0025 (12)	0.0015 (10)	0.0001 (12)
C12	0.0492 (14)	0.0511 (15)	0.0841 (18)	−0.0052 (12)	0.0031 (13)	−0.0113 (14)
C13	0.0486 (14)	0.0705 (18)	0.0718 (17)	0.0063 (14)	−0.0117 (12)	−0.0277 (15)
C14	0.0488 (13)	0.0692 (17)	0.0473 (13)	0.0107 (13)	−0.0032 (11)	−0.0150 (12)
C15	0.0456 (12)	0.0507 (14)	0.0485 (12)	0.0018 (11)	0.0028 (10)	−0.0042 (11)

Geometric parameters (Å, º)

Cl—C14	1.745 (2)	C8—C9	1.508 (2)
O1—C1	1.366 (2)	C8—H8A	0.970
O1—C9	1.450 (2)	C8—H8B	0.970
O2—C7	1.219 (2)	C9—C10	1.500 (3)
C1—C2	1.386 (3)	C9—H9	0.980
C1—C6	1.402 (2)	C10—C15	1.381 (3)
C2—C3	1.370 (3)	C10—C11	1.384 (3)
C2—H2	0.930	C11—C12	1.381 (3)
C3—C4	1.391 (3)	C11—H11	0.930
C3—H3	0.930	C12—C13	1.384 (3)
C4—C5	1.357 (3)	C12—H12	0.930
C4—H4	0.930	C13—C14	1.366 (3)
C5—C6	1.401 (3)	C13—H13	0.930
C5—H5	0.930	C14—C15	1.376 (3)
C6—C7	1.470 (3)	C15—H15	0.930
C7—C8	1.505 (3)
C1—O1—C9	113.58 (14)	C9—C8—H8B	109.4
O1—C1—C2	117.26 (18)	H8A—C8—H8B	108.0
O1—C1—C6	122.39 (18)	O1—C9—C10	108.16 (15)
C2—C1—C6	120.33 (19)	O1—C9—C8	109.65 (15)
C3—C2—C1	119.4 (2)	C10—C9—C8	113.97 (17)
C3—C2—H2	120.3	O1—C9—H9	108.3
C1—C2—H2	120.3	C10—C9—H9	108.3
C2—C3—C4	121.3 (2)	C8—C9—H9	108.3
C2—C3—H3	119.4	C15—C10—C11	119.08 (19)
C4—C3—H3	119.4	C15—C10—C9	119.50 (19)
C5—C4—C3	119.2 (2)	C11—C10—C9	121.40 (18)
C5—C4—H4	120.4	C12—C11—C10	120.6 (2)
C3—C4—H4	120.4	C12—C11—H11	119.7
C4—C5—C6	121.4 (2)	C10—C11—H11	119.7
C4—C5—H5	119.3	C11—C12—C13	120.0 (2)
C6—C5—H5	119.3	C11—C12—H12	120.0
C5—C6—C1	118.2 (2)	C13—C12—H12	120.0
C5—C6—C7	121.82 (19)	C14—C13—C12	119.0 (2)
C1—C6—C7	119.90 (18)	C14—C13—H13	120.5
O2—C7—C6	122.78 (19)	C12—C13—H13	120.5
O2—C7—C8	122.32 (19)	C13—C14—C15	121.6 (2)
C6—C7—C8	114.88 (17)	C13—C14—Cl	119.30 (18)
C7—C8—C9	111.08 (17)	C15—C14—Cl	119.1 (2)
C7—C8—H8A	109.4	C14—C15—C10	119.7 (2)
C9—C8—H8A	109.4	C14—C15—H15	120.1
C7—C8—H8B	109.4	C10—C15—H15	120.1
C9—O1—C1—C2	−154.59 (17)	C1—O1—C9—C10	178.92 (16)
C9—O1—C1—C6	24.0 (3)	C1—O1—C9—C8	−56.2 (2)
O1—C1—C2—C3	176.57 (18)	C7—C8—C9—O1	58.2 (2)
C6—C1—C2—C3	−2.1 (3)	C7—C8—C9—C10	179.61 (17)
C1—C2—C3—C4	−0.7 (3)	O1—C9—C10—C15	−130.18 (18)
C2—C3—C4—C5	2.3 (3)	C8—C9—C10—C15	107.6 (2)
C3—C4—C5—C6	−1.2 (3)	O1—C9—C10—C11	51.2 (2)
C4—C5—C6—C1	−1.5 (3)	C8—C9—C10—C11	−71.0 (2)
C4—C5—C6—C7	176.17 (18)	C15—C10—C11—C12	−0.3 (3)
O1—C1—C6—C5	−175.45 (17)	C9—C10—C11—C12	178.29 (19)
C2—C1—C6—C5	3.1 (3)	C10—C11—C12—C13	0.0 (3)
O1—C1—C6—C7	6.9 (3)	C11—C12—C13—C14	0.8 (3)
C2—C1—C6—C7	−174.58 (18)	C12—C13—C14—C15	−1.2 (3)
C5—C6—C7—O2	−2.4 (3)	C12—C13—C14—Cl	177.08 (16)
C1—C6—C7—O2	175.19 (19)	C13—C14—C15—C10	0.9 (3)
C5—C6—C7—C8	179.07 (18)	Cl—C14—C15—C10	−177.41 (15)
C1—C6—C7—C8	−3.3 (3)	C11—C10—C15—C14	−0.1 (3)
O2—C7—C8—C9	152.85 (19)	C9—C10—C15—C14	−178.73 (19)
C6—C7—C8—C9	−28.6 (2)