6-Chloro-4-(4-methyl­phen­oxy­meth­yl)-2H-chromen-2-one

Gowda, R.; Gowda, K.V.A.; Basanagouda, M.; Kulkarni, M.V.

doi:10.1107/S1600536811019258

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1650

doi:10.1107/S1600536811019258

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6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one

Ramakrishna Gowda,^a ^* K.V. Arjuna Gowda,^b Mahantesha Basanagouda ^c and Manohar V. Kulkarni ^c

^aDepartment of Physics, Govt. College for Women, Kolar 563 101, Karnataka, India, ^bDepartment of Physics, Govt. College for Women, Mandya 571 401, Karnataka, India, and ^cDepartment of Chemistry, Karnatak University, Dharwad 580 003, Karnataka, India
^*Correspondence e-mail: kvarjunagowda@gmail.com

(Received 25 April 2011; accepted 20 May 2011; online 18 June 2011)

In the title compound, C₁₇H₁₃ClO₃, the coumarin and phenoxy moieties are essentially co-planar, making a dihedral angle of 1.99 (7)°. The phenoxy moiety is oriented antiperiplanar with respect to the coumarin ring as indicated by the C—C—O—C angle of −179.97 (16)°. In the crystal, the sheet-like packing is stabilized by intermolecular C—H⋯O and C—H⋯Cl hydrogen bonds.

Related literature

For the structure of 7-methyl-4-tolyloxymethylcoumarin, see: Vasudevan et al. (1990 ).

Experimental

Crystal data

C₁₇H₁₃ClO₃
M_r = 300.72
Monoclinic, P 2₁ /c
a = 15.3068 (5) Å
b = 6.9353 (2) Å
c = 14.9566 (5) Å
β = 116.923 (2)°
V = 1415.66 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.932, T_max = 0.967
16899 measured reflections
3818 independent reflections
2448 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.170
S = 1.08
3818 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O2ⁱ	0.97	2.47	3.303 (5)	143
C4—H4⋯O2ⁱ	0.93	2.69	3.553 (4)	154
C1—H1⋯Cl1ⁱⁱ	0.93	2.88	3.693 (4)	146
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019258/vm2090sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019258/vm2090Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019258/vm2090Isup3.cml

checkCIF report

Comment top

The first report on X-ray diffraction studies on 4-aryloxymethylcoumarins has revealed that in solid state the molecules exist as head-tail dimers as observed in the case of 7-methyl-4-tolyloxymethylcoumarin (Vasudevan et al., 1990). In the light of these observations a chloro substituted 4-aryloxymethylcoumarin has been subjected to X-ray diffraction studies. A significant bond deviation is observed at C5—C7 (1.449 (2) Å) due to the bridging of α-pyrone and benzene ring at C5 and the substituent present at C7. This is also reflected at C8—C9 and C7—C10 due to the presence of O2 at C9 and a phenoxy group at C10, respectively. Significant bond angle deviations are observed at C6—C5—C4 (117.91 (17)°) and C6—C5—C7 (117.61 (18)°). Another significant bond angle deviation is observed at C15—C14—C13 (117.46 (18)°) due to presence of the electron donating methyl group on C14. The molecules are oriented as parallel layers along the c axis as shown in Fig 2. The sheet-like packing is stabilized by intermolecular C—H···O and C—H···Cl hydrogen bonds (Table 1, Fig. 3).

Related literature top

For the structure of 7-methyl-4-tolyloxymethylcoumarin, see: Vasudevan et al. (1990).

Experimental top

A mixture of 4-methyl-phenol (10 mmol) and anhydrous potassium carbonate (10 mmol) was stirred for 30 minutes in dry acetone (30 ml). To this, 6-chloro-4-bromomethylcoumarin (10 mmol) was added and the stirring was continued for 24 h. Then, the resulting reaction mixture was poured to crushed ice. The separated solid was filtered and washed with 1:1 HCl (30 ml) and with water. Then product 6-chloro-4-[(4-methyl)phenoxymethyl]coumarin was recrystallized from ethyl acetate.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. Packing diagram viewed down a axis and molecules oriented as parallel layers along c axis.
	Fig. 3. Packing diagram showing C—H···O and C—H···Cl hydrogen bonding.

6-Chloro-4-(4-methylphenoxymethyl)-2H-chromen-2-one top

Crystal data top

C₁₇H₁₃ClO₃	F(000) = 624
M_r = 300.72	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4071 reflections
a = 15.3068 (5) Å	θ = 2.7–28.3°
b = 6.9353 (2) Å	µ = 0.28 mm⁻¹
c = 14.9566 (5) Å	T = 293 K
β = 116.923 (2)°	Block, colourless
V = 1415.66 (8) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3818 independent reflections
Radiation source: fine-focus sealed tube	2448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω and ϕ scans	θ_max = 29.2°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −20→20
T_min = 0.932, T_max = 0.967	k = −9→6
16899 measured reflections	l = −20→20

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0833P)² + 0.2177P] where P = (F_o² + 2F_c²)/3
3818 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₃ClO₃	V = 1415.66 (8) Å³
M_r = 300.72	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.3068 (5) Å	µ = 0.28 mm⁻¹
b = 6.9353 (2) Å	T = 293 K
c = 14.9566 (5) Å	0.30 × 0.20 × 0.20 mm
β = 116.923 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3818 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2448 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.967	R_int = 0.038
16899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.08	Δρ_max = 0.27 e Å⁻³
3818 reflections	Δρ_min = −0.22 e Å⁻³
191 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.09025 (16)	0.1827 (4)	0.68708 (19)	0.0627 (7)
H1	0.0528	0.1718	0.7215	0.075*
C2	0.04581 (17)	0.2170 (4)	0.5863 (2)	0.0652 (7)
H2	−0.0219	0.2299	0.5514	0.078*
C3	0.10297 (15)	0.2323 (4)	0.53657 (16)	0.0509 (5)
C4	0.20280 (14)	0.2106 (3)	0.58555 (15)	0.0430 (5)
H4	0.2395	0.2191	0.5503	0.052*
C5	0.24892 (13)	0.1756 (3)	0.68853 (14)	0.0371 (4)
C6	0.19059 (15)	0.1644 (3)	0.73768 (16)	0.0448 (5)
C7	0.35374 (13)	0.1530 (3)	0.74835 (14)	0.0359 (4)
C8	0.39041 (14)	0.1275 (3)	0.84735 (15)	0.0428 (5)
H8	0.4578	0.1139	0.8853	0.051*
C9	0.32906 (15)	0.1204 (3)	0.89761 (16)	0.0482 (5)
C10	0.41673 (12)	0.1566 (3)	0.69576 (14)	0.0384 (4)
H10A	0.4010	0.0477	0.6503	0.046*
H10B	0.4049	0.2741	0.6568	0.046*
C11	0.58438 (13)	0.1494 (3)	0.73188 (15)	0.0380 (4)
C12	0.56245 (14)	0.1461 (3)	0.63200 (15)	0.0437 (5)
H12	0.4976	0.1427	0.5829	0.052*
C13	0.63822 (15)	0.1481 (3)	0.60532 (17)	0.0488 (5)
H13	0.6233	0.1448	0.5377	0.059*
C14	0.73516 (15)	0.1549 (3)	0.67619 (18)	0.0505 (5)
C15	0.75450 (15)	0.1587 (3)	0.77520 (19)	0.0525 (6)
H15	0.8193	0.1637	0.8243	0.063*
C16	0.68085 (14)	0.1553 (3)	0.80433 (16)	0.0458 (5)
H16	0.6960	0.1571	0.8720	0.055*
C17	0.81634 (18)	0.1592 (4)	0.6449 (2)	0.0747 (8)
H17A	0.8295	0.2904	0.6344	0.112*
H17B	0.7965	0.0876	0.5839	0.112*
H17C	0.8745	0.1026	0.6967	0.112*
O1	0.23009 (10)	0.1370 (2)	0.83898 (11)	0.0524 (4)
O2	0.35626 (12)	0.1007 (3)	0.98589 (11)	0.0684 (5)
O3	0.51603 (9)	0.1474 (2)	0.76774 (10)	0.0459 (4)
Cl1	0.04586 (4)	0.28400 (13)	0.40961 (5)	0.0790 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0443 (12)	0.093 (2)	0.0644 (14)	−0.0023 (12)	0.0368 (11)	−0.0043 (13)
C2	0.0363 (10)	0.099 (2)	0.0655 (15)	0.0039 (12)	0.0278 (10)	−0.0017 (14)
C3	0.0389 (10)	0.0683 (15)	0.0476 (11)	0.0036 (10)	0.0213 (9)	0.0021 (10)
C4	0.0393 (10)	0.0470 (12)	0.0499 (11)	0.0003 (9)	0.0266 (9)	−0.0001 (9)
C5	0.0359 (9)	0.0345 (10)	0.0472 (10)	−0.0020 (7)	0.0243 (8)	−0.0036 (8)
C6	0.0444 (10)	0.0494 (13)	0.0495 (11)	−0.0037 (9)	0.0291 (9)	−0.0048 (9)
C7	0.0382 (9)	0.0289 (9)	0.0473 (10)	−0.0025 (7)	0.0252 (8)	−0.0040 (8)
C8	0.0407 (10)	0.0450 (12)	0.0470 (11)	−0.0061 (8)	0.0236 (8)	−0.0072 (9)
C9	0.0512 (11)	0.0538 (14)	0.0463 (11)	−0.0096 (10)	0.0278 (9)	−0.0128 (10)
C10	0.0314 (8)	0.0445 (11)	0.0413 (9)	0.0016 (8)	0.0183 (7)	0.0024 (8)
C11	0.0337 (9)	0.0344 (10)	0.0497 (10)	0.0020 (7)	0.0223 (8)	0.0023 (8)
C12	0.0342 (9)	0.0480 (12)	0.0501 (11)	−0.0015 (8)	0.0201 (8)	−0.0021 (9)
C13	0.0473 (11)	0.0518 (13)	0.0556 (12)	−0.0010 (10)	0.0308 (10)	−0.0020 (10)
C14	0.0416 (11)	0.0450 (12)	0.0747 (15)	0.0031 (9)	0.0351 (11)	−0.0021 (11)
C15	0.0299 (9)	0.0511 (13)	0.0724 (15)	0.0033 (9)	0.0195 (9)	0.0012 (11)
C16	0.0387 (10)	0.0475 (12)	0.0492 (11)	0.0051 (9)	0.0181 (8)	0.0031 (9)
C17	0.0522 (14)	0.084 (2)	0.108 (2)	0.0047 (13)	0.0538 (15)	−0.0040 (16)
O1	0.0474 (8)	0.0715 (11)	0.0489 (8)	−0.0054 (7)	0.0310 (7)	−0.0060 (7)
O2	0.0664 (10)	0.1026 (15)	0.0437 (9)	−0.0135 (10)	0.0315 (8)	−0.0150 (9)
O3	0.0328 (7)	0.0636 (10)	0.0443 (8)	0.0027 (6)	0.0201 (6)	0.0057 (6)
Cl1	0.0481 (3)	0.1308 (7)	0.0550 (4)	0.0162 (3)	0.0206 (3)	0.0183 (4)

Geometric parameters (Å, º) top

C1—C2	1.365 (3)	C10—O3	1.411 (2)
C1—C6	1.377 (3)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C3	1.385 (3)	C11—O3	1.375 (2)
C2—H2	0.9300	C11—C12	1.375 (3)
C3—C4	1.371 (3)	C11—C16	1.381 (3)
C3—Cl1	1.731 (2)	C12—C13	1.387 (3)
C4—C5	1.394 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.380 (3)
C5—C6	1.392 (2)	C13—H13	0.9300
C5—C7	1.449 (2)	C14—C15	1.373 (3)
C6—O1	1.367 (2)	C14—C17	1.513 (3)
C7—C8	1.336 (3)	C15—C16	1.381 (3)
C7—C10	1.495 (2)	C15—H15	0.9300
C8—C9	1.445 (3)	C16—H16	0.9300
C8—H8	0.9300	C17—H17A	0.9600
C9—O2	1.199 (2)	C17—H17B	0.9600
C9—O1	1.369 (3)	C17—H17C	0.9600

C2—C1—C6	119.81 (19)	O3—C10—H10B	109.9
C2—C1—H1	120.1	C7—C10—H10B	109.9
C6—C1—H1	120.1	H10A—C10—H10B	108.3
C1—C2—C3	119.1 (2)	O3—C11—C12	124.69 (16)
C1—C2—H2	120.5	O3—C11—C16	115.23 (17)
C3—C2—H2	120.5	C12—C11—C16	120.08 (17)
C4—C3—C2	121.8 (2)	C11—C12—C13	119.20 (18)
C4—C3—Cl1	119.73 (16)	C11—C12—H12	120.4
C2—C3—Cl1	118.47 (17)	C13—C12—H12	120.4
C3—C4—C5	119.56 (18)	C14—C13—C12	121.9 (2)
C3—C4—H4	120.2	C14—C13—H13	119.1
C5—C4—H4	120.2	C12—C13—H13	119.1
C6—C5—C4	117.91 (17)	C15—C14—C13	117.46 (18)
C6—C5—C7	117.61 (18)	C15—C14—C17	121.8 (2)
C4—C5—C7	124.48 (16)	C13—C14—C17	120.7 (2)
O1—C6—C1	116.47 (17)	C14—C15—C16	122.1 (2)
O1—C6—C5	121.71 (18)	C14—C15—H15	118.9
C1—C6—C5	121.8 (2)	C16—C15—H15	118.9
C8—C7—C5	119.38 (16)	C15—C16—C11	119.2 (2)
C8—C7—C10	122.52 (17)	C15—C16—H16	120.4
C5—C7—C10	118.09 (16)	C11—C16—H16	120.4
C7—C8—C9	122.34 (18)	C14—C17—H17A	109.5
C7—C8—H8	118.8	C14—C17—H17B	109.5
C9—C8—H8	118.8	H17A—C17—H17B	109.5
O2—C9—O1	116.54 (18)	C14—C17—H17C	109.5
O2—C9—C8	126.4 (2)	H17A—C17—H17C	109.5
O1—C9—C8	117.07 (17)	H17B—C17—H17C	109.5
O3—C10—C7	109.05 (15)	C6—O1—C9	121.85 (15)
O3—C10—H10A	109.9	C11—O3—C10	116.67 (14)
C7—C10—H10A	109.9

C6—C1—C2—C3	0.1 (4)	C7—C8—C9—O1	1.3 (3)
C1—C2—C3—C4	1.2 (4)	C8—C7—C10—O3	−5.3 (3)
C1—C2—C3—Cl1	−177.8 (2)	C5—C7—C10—O3	175.47 (16)
C2—C3—C4—C5	−1.2 (4)	O3—C11—C12—C13	−179.84 (19)
Cl1—C3—C4—C5	177.74 (16)	C16—C11—C12—C13	0.3 (3)
C3—C4—C5—C6	0.0 (3)	C11—C12—C13—C14	−0.5 (3)
C3—C4—C5—C7	−179.1 (2)	C12—C13—C14—C15	0.3 (3)
C2—C1—C6—O1	177.8 (2)	C12—C13—C14—C17	−179.3 (2)
C2—C1—C6—C5	−1.4 (4)	C13—C14—C15—C16	0.2 (3)
C4—C5—C6—O1	−177.77 (18)	C17—C14—C15—C16	179.8 (2)
C7—C5—C6—O1	1.4 (3)	C14—C15—C16—C11	−0.5 (3)
C4—C5—C6—C1	1.3 (3)	O3—C11—C16—C15	−179.67 (19)
C7—C5—C6—C1	−179.5 (2)	C12—C11—C16—C15	0.2 (3)
C6—C5—C7—C8	−1.7 (3)	C1—C6—O1—C9	−178.8 (2)
C4—C5—C7—C8	177.35 (19)	C5—C6—O1—C9	0.4 (3)
C6—C5—C7—C10	177.49 (17)	O2—C9—O1—C6	178.5 (2)
C4—C5—C7—C10	−3.4 (3)	C8—C9—O1—C6	−1.7 (3)
C5—C7—C8—C9	0.4 (3)	C12—C11—O3—C10	−4.7 (3)
C10—C7—C8—C9	−178.76 (19)	C16—C11—O3—C10	175.20 (17)
C7—C8—C9—O2	−178.9 (2)	C7—C10—O3—C11	−179.97 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.97	2.47	3.303 (5)	143
C4—H4···O2ⁱ	0.93	2.69	3.553 (4)	154
C1—H1···Cl1ⁱⁱ	0.93	2.88	3.693 (4)	146

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃ClO₃
M_r	300.72
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	15.3068 (5), 6.9353 (2), 14.9566 (5)
β (°)	116.923 (2)
V (Å³)	1415.66 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.932, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	16899, 3818, 2448
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.170, 1.08
No. of reflections	3818
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O2ⁱ	0.97	2.47	3.303 (5)	143
C4—H4···O2ⁱ	0.93	2.69	3.553 (4)	154
C1—H1···Cl1ⁱⁱ	0.93	2.88	3.693 (4)	146

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) x, −y+1/2, z+1/2.

Acknowledgements

RG thanks the MVJ College of Engineering, Bangalore-67 (VTU Research Center), for providing research facilities. The authors also thank the SAIF, IIT-Madras, Chennai, for the data collection

References

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