4-Chloro-phenyl 2-oxo-2H-chromene-3-carboxyl-ate.

In title compound, C(16)H(9)ClO(4), the coumarin ring system is approximately planar [maximum deviation = 0.056 (1) Å] and is oriented with respect to the benzene ring at an angle of 22.60 (7)°. Inter-molecular C-H⋯O hydrogen bonding is present in the crystal.

Related literature

For the biochemical properties of related compounds, see: Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Finn et al. (2002 ▶); Gursoy & Karali (2003 ▶); Borges et al. (2005 ▶). For the synthesis, see: Zhou et al. (2008 ▶).

Experimental

Crystal data

C16H9ClO4

M = 300.68

Monoclinic,

a = 15.7586 (6) Å

b = 7.0694 (2) Å

c = 12.7167 (6) Å

β = 113.037 (5)°

V = 1303.70 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 135 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.99, T max = 1.00

5907 measured reflections

2662 independent reflections

2059 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.092

S = 1.04

2662 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003376/xu5453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003376/xu5453Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003376/xu5453Isup3.cml

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

C16H9ClO4	F(000) = 616
Mr = 300.68	Dx = 1.532 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 15.7586 (6) Å	Cell parameters from 1865 reflections
b = 7.0694 (2) Å	θ = 3.2–29.0°
c = 12.7167 (6) Å	µ = 0.31 mm−1
β = 113.037 (5)°	T = 135 K
V = 1303.70 (9) Å3	Block, colorless
Z = 4	0.35 × 0.30 × 0.25 mm

Agilent Xcalibur Eos diffractometer	2662 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2059 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 3.2°
ω scans	h = −19→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
Tmin = 0.99, Tmax = 1.00	l = −15→15
5907 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0338P)2 + 0.3053P] where P = (Fo2 + 2Fc2)/3
2662 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.25 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	0.43760 (4)	0.34411 (8)	0.78566 (6)	0.04706 (19)
O1	0.06760 (8)	0.42742 (17)	0.78729 (10)	0.0207 (3)
O2	0.08852 (9)	0.22946 (18)	0.93513 (11)	0.0261 (3)
O3	−0.19477 (9)	0.33623 (17)	0.87422 (11)	0.0257 (3)
O4	−0.05715 (9)	0.31077 (18)	1.01368 (11)	0.0282 (3)
C1	0.32829 (13)	0.3605 (3)	0.78930 (18)	0.0278 (5)
C2	0.25165 (13)	0.3316 (3)	0.69014 (17)	0.0268 (4)
H2	0.2583	0.2995	0.6212	0.032*
C3	0.16458 (13)	0.3502 (2)	0.69216 (16)	0.0224 (4)
H3	0.1108	0.3305	0.6249	0.027*
C4	0.15761 (12)	0.3978 (2)	0.79363 (15)	0.0198 (4)
C5	0.23437 (13)	0.4279 (3)	0.89344 (15)	0.0233 (4)
H5	0.2278	0.4620	0.9621	0.028*
C6	0.32111 (13)	0.4072 (3)	0.89098 (17)	0.0281 (4)
H6	0.3750	0.4249	0.9585	0.034*
C7	0.03900 (13)	0.3290 (2)	0.85939 (15)	0.0194 (4)
C8	−0.06155 (12)	0.3544 (2)	0.82490 (15)	0.0189 (4)
C9	−0.09937 (13)	0.3309 (2)	0.91268 (16)	0.0216 (4)
C10	−0.25169 (13)	0.3560 (2)	0.76084 (16)	0.0235 (4)
C11	−0.21523 (13)	0.3850 (2)	0.67830 (16)	0.0218 (4)
C12	−0.11740 (13)	0.3840 (2)	0.71464 (15)	0.0199 (4)
H12	−0.0910	0.4045	0.6600	0.024*
C13	−0.27666 (14)	0.4046 (3)	0.56409 (17)	0.0276 (4)
H13	−0.2535	0.4265	0.5065	0.033*
C14	−0.37008 (14)	0.3924 (3)	0.53509 (18)	0.0338 (5)
H14	−0.4114	0.4052	0.4575	0.041*
C15	−0.40409 (14)	0.3612 (3)	0.6193 (2)	0.0352 (5)
H15	−0.4688	0.3515	0.5985	0.042*
C16	−0.34558 (14)	0.3440 (3)	0.73263 (19)	0.0305 (5)
H16	−0.3692	0.3243	0.7900	0.037*

	U11	U22	U33	U12	U13	U23
Cl1	0.0280 (3)	0.0510 (4)	0.0715 (4)	0.0092 (3)	0.0296 (3)	0.0160 (3)
O1	0.0195 (7)	0.0249 (7)	0.0200 (7)	0.0019 (6)	0.0102 (5)	0.0047 (5)
O2	0.0250 (7)	0.0309 (7)	0.0226 (7)	0.0051 (6)	0.0096 (6)	0.0066 (6)
O3	0.0240 (7)	0.0298 (7)	0.0276 (7)	−0.0018 (6)	0.0147 (6)	−0.0031 (6)
O4	0.0325 (8)	0.0361 (8)	0.0192 (7)	−0.0040 (7)	0.0134 (6)	−0.0015 (6)
C1	0.0216 (10)	0.0223 (10)	0.0436 (12)	0.0038 (8)	0.0173 (9)	0.0083 (9)
C2	0.0328 (11)	0.0231 (10)	0.0310 (11)	0.0017 (9)	0.0196 (9)	0.0028 (8)
C3	0.0259 (10)	0.0196 (9)	0.0216 (10)	−0.0023 (8)	0.0093 (8)	0.0005 (7)
C4	0.0201 (9)	0.0168 (8)	0.0244 (10)	0.0017 (8)	0.0107 (8)	0.0038 (7)
C5	0.0257 (10)	0.0230 (10)	0.0208 (10)	−0.0012 (8)	0.0086 (8)	0.0015 (7)
C6	0.0210 (10)	0.0264 (10)	0.0318 (11)	−0.0004 (9)	0.0049 (9)	0.0061 (8)
C7	0.0256 (10)	0.0195 (9)	0.0149 (9)	−0.0018 (8)	0.0099 (8)	−0.0030 (7)
C8	0.0222 (9)	0.0155 (9)	0.0222 (9)	−0.0010 (8)	0.0122 (8)	−0.0020 (7)
C9	0.0241 (10)	0.0180 (9)	0.0265 (11)	−0.0027 (8)	0.0140 (8)	−0.0034 (8)
C10	0.0228 (10)	0.0181 (9)	0.0297 (11)	−0.0006 (8)	0.0105 (8)	−0.0037 (8)
C11	0.0223 (10)	0.0167 (9)	0.0267 (10)	0.0012 (8)	0.0098 (8)	−0.0018 (7)
C12	0.0253 (10)	0.0156 (8)	0.0216 (9)	−0.0006 (8)	0.0123 (8)	−0.0017 (7)
C13	0.0285 (11)	0.0224 (10)	0.0292 (11)	0.0039 (9)	0.0083 (9)	0.0004 (8)
C14	0.0257 (11)	0.0289 (11)	0.0376 (12)	0.0066 (9)	0.0025 (9)	0.0002 (9)
C15	0.0192 (10)	0.0266 (11)	0.0554 (14)	0.0038 (9)	0.0098 (10)	−0.0021 (10)
C16	0.0249 (11)	0.0255 (10)	0.0450 (13)	0.0011 (9)	0.0178 (10)	−0.0019 (9)

Cl1—C1	1.7450 (19)	C6—H6	0.9500
O1—C4	1.404 (2)	C7—C8	1.480 (2)
O1—C7	1.361 (2)	C8—C9	1.466 (2)
O2—C7	1.201 (2)	C8—C12	1.349 (2)
O3—C9	1.388 (2)	C10—C11	1.395 (3)
O3—C10	1.375 (2)	C10—C16	1.382 (3)
O4—C9	1.202 (2)	C11—C12	1.426 (3)
C1—C2	1.378 (3)	C11—C13	1.402 (3)
C1—C6	1.381 (3)	C12—H12	0.9500
C2—H2	0.9500	C13—H13	0.9500
C2—C3	1.388 (3)	C13—C14	1.373 (3)
C3—H3	0.9500	C14—H14	0.9500
C3—C4	1.379 (2)	C14—C15	1.390 (3)
C4—C5	1.385 (2)	C15—H15	0.9500
C5—H5	0.9500	C15—C16	1.379 (3)
C5—C6	1.387 (3)	C16—H16	0.9500
C7—O1—C4	118.58 (13)	C12—C8—C9	120.99 (17)
C10—O3—C9	122.99 (14)	O3—C9—C8	115.83 (16)
C2—C1—Cl1	119.13 (16)	O4—C9—O3	116.77 (16)
C2—C1—C6	121.90 (18)	O4—C9—C8	127.39 (18)
C6—C1—Cl1	118.94 (16)	O3—C10—C11	120.82 (17)
C1—C2—H2	120.4	O3—C10—C16	117.30 (17)
C1—C2—C3	119.20 (18)	C16—C10—C11	121.88 (19)
C3—C2—H2	120.4	C10—C11—C12	117.83 (17)
C2—C3—H3	120.6	C10—C11—C13	118.25 (18)
C4—C3—C2	118.79 (17)	C13—C11—C12	123.85 (18)
C4—C3—H3	120.6	C8—C12—C11	121.38 (17)
C3—C4—O1	115.54 (16)	C8—C12—H12	119.3
C3—C4—C5	122.29 (17)	C11—C12—H12	119.3
C5—C4—O1	122.01 (16)	C11—C13—H13	119.8
C4—C5—H5	120.7	C14—C13—C11	120.33 (19)
C4—C5—C6	118.56 (17)	C14—C13—H13	119.8
C6—C5—H5	120.7	C13—C14—H14	120.0
C1—C6—C5	119.26 (18)	C13—C14—C15	119.9 (2)
C1—C6—H6	120.4	C15—C14—H14	120.0
C5—C6—H6	120.4	C14—C15—H15	119.4
O1—C7—C8	109.68 (15)	C16—C15—C14	121.15 (19)
O2—C7—O1	123.86 (17)	C16—C15—H15	119.4
O2—C7—C8	126.34 (17)	C10—C16—H16	120.8
C9—C8—C7	117.88 (16)	C15—C16—C10	118.43 (19)
C12—C8—C7	120.95 (16)	C15—C16—H16	120.8
Cl1—C1—C2—C3	−178.09 (13)	C7—C8—C9—O3	−173.49 (15)
Cl1—C1—C6—C5	177.43 (14)	C7—C8—C9—O4	7.9 (3)
O1—C4—C5—C6	−175.94 (16)	C7—C8—C12—C11	172.06 (16)
O1—C7—C8—C9	−154.96 (14)	C9—O3—C10—C11	−4.4 (2)
O1—C7—C8—C12	29.9 (2)	C9—O3—C10—C16	174.89 (16)
O2—C7—C8—C9	28.8 (3)	C9—C8—C12—C11	−2.9 (3)
O2—C7—C8—C12	−146.26 (18)	C10—O3—C9—O4	−179.14 (15)
O3—C10—C11—C12	3.0 (2)	C10—O3—C9—C8	2.1 (2)
O3—C10—C11—C13	−179.87 (15)	C10—C11—C12—C8	0.6 (3)
O3—C10—C16—C15	−179.25 (16)	C10—C11—C13—C14	−1.0 (3)
C1—C2—C3—C4	0.3 (3)	C11—C10—C16—C15	0.1 (3)
C2—C1—C6—C5	−0.8 (3)	C11—C13—C14—C15	0.3 (3)
C2—C3—C4—O1	175.57 (15)	C12—C8—C9—O3	1.6 (2)
C2—C3—C4—C5	0.1 (3)	C12—C8—C9—O4	−177.06 (18)
C3—C4—C5—C6	−0.7 (3)	C12—C11—C13—C14	175.89 (18)
C4—O1—C7—O2	6.5 (2)	C13—C11—C12—C8	−176.34 (16)
C4—O1—C7—C8	−169.80 (14)	C13—C14—C15—C16	0.7 (3)
C4—C5—C6—C1	1.0 (3)	C14—C15—C16—C10	−0.8 (3)
C6—C1—C2—C3	0.1 (3)	C16—C10—C11—C12	−176.25 (17)
C7—O1—C4—C3	126.23 (16)	C16—C10—C11—C13	0.8 (3)
C7—O1—C4—C5	−58.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.34	3.061 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.34	3.061 (2)	133

Symmetry code: (i) .