4-(Oct-yloxy)phenyl 2-oxo-2H-chromene-3-carboxyl-ate.

In the title compound, C(24)H(26)O(5), the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.029 (2) Å from the best-fit mean plane incorporating both rings. The dihedral angle between the 2H-chromene ring system and the benzene ring is 21.00 (1)°. In the crystal, pairs of C-H⋯O hydrogen bonds generate an R(2) (2)(8) ring pattern. These contacts are bolstered by weaker bifurcated C-H⋯O hydrogen bonds.

Related literature

For general background to coumarin derivatives and their biological and technological applications, see: Georgieva et al. (2004 ▶); Creaven et al. (2005 ▶); Morita et al. (2005 ▶); Tian et al. (2003 ▶); Iliopoulos et al. (2010 ▶); Hejchman et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H26O5

M = 394.45

Monoclinic,

a = 14.464 (3) Å

b = 6.7548 (15) Å

c = 21.381 (5) Å

β = 91.663 (8)°

V = 2088.0 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.29 × 0.25 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.975, T max = 0.982

22609 measured reflections

3615 independent reflections

1926 reflections with I > 2σ(I)

R int = 0.084

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.146

S = 0.94

3615 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000214/sj5291sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000214/sj5291Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000214/sj5291Isup3.cml

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

C24H26O5	F(000) = 840
Mr = 394.45	Dx = 1.255 Mg m−3
Monoclinic, P21/n	Melting point: 580 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.464 (3) Å	Cell parameters from 3615 reflections
b = 6.7548 (15) Å	θ = 3.2–25.0°
c = 21.381 (5) Å	µ = 0.09 mm−1
β = 91.663 (8)°	T = 293 K
V = 2088.0 (8) Å3	Needles, colourless
Z = 4	0.29 × 0.25 × 0.21 mm

Bruker SMART CCD area-detector diffractometer	3615 independent reflections
Radiation source: fine-focus sealed tube	1926 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.084
ω and φ scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −17→16
Tmin = 0.975, Tmax = 0.982	k = −8→5
22609 measured reflections	l = −25→25

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H-atom parameters constrained
wR(F2) = 0.146	w = 1/[σ2(Fo2) + (0.077P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
3615 reflections	Δρmax = 0.18 e Å−3
264 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (7)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.11082 (14)	0.0294 (3)	−0.01675 (8)	0.0705 (6)
O2	0.11756 (15)	−0.1104 (3)	0.07552 (9)	0.0826 (7)
O3	0.06844 (14)	0.1538 (3)	0.17685 (9)	0.0744 (6)
O4	0.14523 (12)	0.4373 (2)	0.16091 (7)	0.0610 (5)
O5	0.14206 (14)	0.7392 (3)	0.40100 (8)	0.0730 (6)
C1	0.1075 (2)	0.1595 (5)	−0.11861 (13)	0.0755 (9)
H1	0.1043	0.0314	−0.1345	0.091*
C2	0.1090 (2)	0.3196 (5)	−0.15818 (14)	0.0827 (9)
H2	0.1062	0.2995	−0.2012	0.099*
C3	0.1146 (2)	0.5101 (5)	−0.13485 (14)	0.0775 (9)
H3	0.1165	0.6174	−0.1620	0.093*
C4	0.11723 (19)	0.5398 (4)	−0.07203 (13)	0.0682 (8)
H4	0.1203	0.6682	−0.0564	0.082*
C5	0.11538 (17)	0.3810 (4)	−0.03071 (11)	0.0509 (6)
C6	0.11088 (18)	0.1917 (4)	−0.05564 (12)	0.0557 (7)
C7	0.11337 (19)	0.0428 (4)	0.04771 (12)	0.0603 (7)
C8	0.11338 (17)	0.2423 (3)	0.07410 (11)	0.0497 (6)
C9	0.11632 (16)	0.3995 (4)	0.03580 (11)	0.0524 (7)
H9	0.1191	0.5255	0.0533	0.063*
C10	0.10603 (18)	0.2654 (4)	0.14224 (12)	0.0531 (7)
C11	0.13845 (18)	0.5046 (4)	0.22323 (11)	0.0535 (7)
C12	0.16625 (19)	0.3932 (4)	0.27383 (12)	0.0639 (8)
H12	0.1845	0.2623	0.2686	0.077*
C13	0.16691 (19)	0.4769 (4)	0.33248 (12)	0.0650 (8)
H13	0.1863	0.4028	0.3671	0.078*
C14	0.13875 (19)	0.6712 (4)	0.34023 (11)	0.0567 (7)
C15	0.11116 (19)	0.7799 (4)	0.28884 (11)	0.0619 (7)
H15	0.0923	0.9104	0.2938	0.074*
C16	0.11120 (19)	0.6972 (4)	0.22990 (11)	0.0591 (7)
H16	0.0929	0.7715	0.1951	0.071*
C17	0.1323 (2)	0.9462 (4)	0.41084 (12)	0.0645 (7)
H17A	0.0739	0.9916	0.3926	0.077*
H17B	0.1819	1.0168	0.3909	0.077*
C18	0.1356 (2)	0.9869 (4)	0.47999 (11)	0.0675 (8)
H18A	0.1914	0.9287	0.4984	0.081*
H18B	0.0831	0.9239	0.4989	0.081*
C19	0.1343 (2)	1.2047 (4)	0.49476 (12)	0.0707 (8)
H19A	0.0812	1.2634	0.4731	0.085*
H19B	0.1893	1.2646	0.4780	0.085*
C20	0.1304 (2)	1.2574 (4)	0.56327 (12)	0.0723 (8)
H20A	0.0761	1.1960	0.5806	0.087*
H20B	0.1843	1.2027	0.5850	0.087*
C21	0.1269 (2)	1.4752 (5)	0.57543 (13)	0.0831 (9)
H21A	0.0717	1.5278	0.5546	0.100*
H21B	0.1797	1.5360	0.5562	0.100*
C22	0.1265 (2)	1.5383 (5)	0.64278 (13)	0.0839 (9)
H22A	0.1818	1.4883	0.6641	0.101*
H22B	0.0734	1.4801	0.6625	0.101*
C23	0.1229 (3)	1.7629 (5)	0.65022 (15)	0.1031 (12)
H23A	0.1746	1.8199	0.6287	0.124*
H23B	0.0666	1.8108	0.6295	0.124*
C24	0.1255 (3)	1.8364 (6)	0.71544 (16)	0.1332 (16)
H24A	0.0720	1.7894	0.7365	0.200*
H24B	0.1256	1.9785	0.7153	0.200*
H24C	0.1804	1.7889	0.7368	0.200*

	U11	U22	U33	U12	U13	U23
O1	0.1120 (16)	0.0356 (11)	0.0641 (12)	−0.0062 (10)	0.0039 (10)	−0.0070 (9)
O2	0.1353 (19)	0.0309 (12)	0.0816 (14)	−0.0007 (11)	0.0057 (12)	0.0064 (10)
O3	0.1055 (16)	0.0459 (12)	0.0723 (12)	−0.0202 (11)	0.0096 (11)	0.0020 (10)
O4	0.0867 (14)	0.0398 (11)	0.0564 (11)	−0.0166 (9)	0.0003 (9)	−0.0004 (9)
O5	0.1129 (17)	0.0487 (13)	0.0570 (12)	0.0036 (10)	−0.0023 (10)	−0.0017 (9)
C1	0.103 (2)	0.059 (2)	0.0653 (19)	−0.0103 (16)	0.0005 (16)	−0.0075 (16)
C2	0.098 (3)	0.090 (3)	0.0596 (18)	−0.0053 (19)	−0.0046 (16)	0.0027 (19)
C3	0.097 (3)	0.066 (2)	0.069 (2)	0.0052 (17)	0.0010 (16)	0.0184 (17)
C4	0.082 (2)	0.0507 (18)	0.0718 (19)	0.0039 (15)	0.0006 (15)	0.0067 (16)
C5	0.0562 (17)	0.0401 (16)	0.0562 (15)	0.0004 (12)	−0.0026 (12)	0.0034 (13)
C6	0.0659 (19)	0.0445 (17)	0.0566 (16)	−0.0040 (13)	−0.0021 (13)	−0.0030 (14)
C7	0.075 (2)	0.0386 (17)	0.0672 (18)	−0.0039 (13)	0.0036 (14)	−0.0036 (15)
C8	0.0573 (17)	0.0307 (14)	0.0608 (16)	−0.0013 (11)	−0.0018 (12)	0.0018 (13)
C9	0.0623 (18)	0.0326 (15)	0.0622 (16)	0.0006 (12)	−0.0020 (12)	−0.0042 (12)
C10	0.0590 (17)	0.0361 (16)	0.0639 (17)	−0.0016 (13)	−0.0025 (13)	0.0025 (14)
C11	0.0697 (19)	0.0365 (15)	0.0542 (15)	−0.0078 (12)	0.0018 (12)	0.0008 (13)
C12	0.087 (2)	0.0373 (15)	0.0670 (18)	0.0048 (14)	−0.0062 (15)	0.0005 (14)
C13	0.092 (2)	0.0435 (17)	0.0588 (17)	0.0071 (14)	−0.0091 (14)	0.0103 (14)
C14	0.0749 (19)	0.0434 (17)	0.0515 (16)	−0.0048 (13)	−0.0026 (13)	0.0046 (13)
C15	0.088 (2)	0.0377 (15)	0.0599 (17)	0.0002 (14)	−0.0029 (14)	0.0023 (13)
C16	0.081 (2)	0.0369 (16)	0.0588 (17)	−0.0038 (13)	−0.0064 (14)	0.0094 (13)
C17	0.077 (2)	0.0548 (19)	0.0615 (17)	0.0054 (14)	0.0026 (13)	−0.0055 (14)
C18	0.069 (2)	0.070 (2)	0.0638 (17)	0.0044 (15)	0.0027 (13)	−0.0025 (15)
C19	0.090 (2)	0.0596 (19)	0.0627 (17)	−0.0049 (16)	0.0010 (15)	−0.0041 (15)
C20	0.086 (2)	0.060 (2)	0.0706 (19)	−0.0015 (15)	0.0053 (15)	−0.0064 (15)
C21	0.106 (3)	0.067 (2)	0.076 (2)	0.0033 (18)	−0.0015 (17)	−0.0039 (17)
C22	0.102 (3)	0.074 (2)	0.077 (2)	0.0031 (18)	0.0093 (17)	−0.0084 (18)
C23	0.152 (3)	0.077 (3)	0.080 (2)	0.015 (2)	0.004 (2)	−0.0115 (19)
C24	0.204 (5)	0.110 (3)	0.088 (3)	0.014 (3)	0.028 (3)	−0.014 (2)

O1—C6	1.376 (3)	C14—C15	1.371 (3)
O1—C7	1.381 (3)	C15—C16	1.379 (3)
O2—C7	1.194 (3)	C15—H15	0.9300
O3—C10	1.198 (3)	C16—H16	0.9300
O4—C10	1.347 (3)	C17—C18	1.503 (3)
O4—C11	1.414 (3)	C17—H17A	0.9700
O5—C14	1.378 (3)	C17—H17B	0.9700
O5—C17	1.422 (3)	C18—C19	1.505 (4)
C1—C6	1.363 (3)	C18—H18A	0.9700
C1—C2	1.374 (4)	C18—H18B	0.9700
C1—H1	0.9300	C19—C20	1.510 (3)
C2—C3	1.381 (4)	C19—H19A	0.9700
C2—H2	0.9300	C19—H19B	0.9700
C3—C4	1.357 (3)	C20—C21	1.496 (4)
C3—H3	0.9300	C20—H20A	0.9700
C4—C5	1.390 (3)	C20—H20B	0.9700
C4—H4	0.9300	C21—C22	1.502 (4)
C5—C6	1.386 (3)	C21—H21A	0.9700
C5—C9	1.427 (3)	C21—H21B	0.9700
C7—C8	1.461 (3)	C22—C23	1.527 (4)
C8—C9	1.342 (3)	C22—H22A	0.9700
C8—C10	1.472 (3)	C22—H22B	0.9700
C9—H9	0.9300	C23—C24	1.479 (4)
C11—C16	1.368 (4)	C23—H23A	0.9700
C11—C12	1.369 (3)	C23—H23B	0.9700
C12—C13	1.375 (3)	C24—H24A	0.9600
C12—H12	0.9300	C24—H24B	0.9600
C13—C14	1.386 (4)	C24—H24C	0.9600
C13—H13	0.9300
C6—O1—C7	123.4 (2)	C15—C16—H16	120.4
C10—O4—C11	121.06 (19)	O5—C17—C18	109.0 (2)
C14—O5—C17	117.82 (19)	O5—C17—H17A	109.9
C6—C1—C2	118.8 (3)	C18—C17—H17A	109.9
C6—C1—H1	120.6	O5—C17—H17B	109.9
C2—C1—H1	120.6	C18—C17—H17B	109.9
C1—C2—C3	120.8 (3)	H17A—C17—H17B	108.3
C1—C2—H2	119.6	C17—C18—C19	112.6 (2)
C3—C2—H2	119.6	C17—C18—H18A	109.1
C4—C3—C2	119.6 (3)	C19—C18—H18A	109.1
C4—C3—H3	120.2	C17—C18—H18B	109.1
C2—C3—H3	120.2	C19—C18—H18B	109.1
C3—C4—C5	120.9 (3)	H18A—C18—H18B	107.8
C3—C4—H4	119.5	C18—C19—C20	115.8 (2)
C5—C4—H4	119.5	C18—C19—H19A	108.3
C6—C5—C4	117.9 (2)	C20—C19—H19A	108.3
C6—C5—C9	117.6 (2)	C18—C19—H19B	108.3
C4—C5—C9	124.5 (2)	C20—C19—H19B	108.3
C1—C6—O1	118.0 (2)	H19A—C19—H19B	107.4
C1—C6—C5	121.8 (2)	C21—C20—C19	113.8 (2)
O1—C6—C5	120.2 (2)	C21—C20—H20A	108.8
O2—C7—O1	116.1 (2)	C19—C20—H20A	108.8
O2—C7—C8	127.4 (2)	C21—C20—H20B	108.8
O1—C7—C8	116.5 (2)	C19—C20—H20B	108.8
C9—C8—C7	119.6 (2)	H20A—C20—H20B	107.7
C9—C8—C10	121.6 (2)	C20—C21—C22	116.5 (3)
C7—C8—C10	118.7 (2)	C20—C21—H21A	108.2
C8—C9—C5	122.6 (2)	C22—C21—H21A	108.2
C8—C9—H9	118.7	C20—C21—H21B	108.2
C5—C9—H9	118.7	C22—C21—H21B	108.2
O3—C10—O4	123.6 (2)	H21A—C21—H21B	107.3
O3—C10—C8	126.3 (2)	C21—C22—C23	112.5 (3)
O4—C10—C8	110.0 (2)	C21—C22—H22A	109.1
C16—C11—C12	121.3 (2)	C23—C22—H22A	109.1
C16—C11—O4	115.6 (2)	C21—C22—H22B	109.1
C12—C11—O4	122.8 (2)	C23—C22—H22B	109.1
C11—C12—C13	119.3 (2)	H22A—C22—H22B	107.8
C11—C12—H12	120.4	C24—C23—C22	115.6 (3)
C13—C12—H12	120.4	C24—C23—H23A	108.4
C12—C13—C14	120.3 (2)	C22—C23—H23A	108.4
C12—C13—H13	119.9	C24—C23—H23B	108.4
C14—C13—H13	119.9	C22—C23—H23B	108.4
C15—C14—O5	125.3 (2)	H23A—C23—H23B	107.4
C15—C14—C13	119.4 (2)	C23—C24—H24A	109.5
O5—C14—C13	115.2 (2)	C23—C24—H24B	109.5
C14—C15—C16	120.5 (3)	H24A—C24—H24B	109.5
C14—C15—H15	119.7	C23—C24—H24C	109.5
C16—C15—H15	119.7	H24A—C24—H24C	109.5
C11—C16—C15	119.2 (2)	H24B—C24—H24C	109.5
C11—C16—H16	120.4
C6—C1—C2—C3	0.6 (5)	C9—C8—C10—O3	148.8 (3)
C1—C2—C3—C4	−1.0 (5)	C7—C8—C10—O3	−28.5 (4)
C2—C3—C4—C5	0.7 (4)	C9—C8—C10—O4	−28.8 (3)
C3—C4—C5—C6	0.1 (4)	C7—C8—C10—O4	153.9 (2)
C3—C4—C5—C9	−178.9 (2)	C10—O4—C11—C16	−131.1 (3)
C2—C1—C6—O1	−179.0 (3)	C10—O4—C11—C12	55.5 (3)
C2—C1—C6—C5	0.2 (4)	C16—C11—C12—C13	−0.1 (4)
C7—O1—C6—C1	−179.5 (2)	O4—C11—C12—C13	172.9 (2)
C7—O1—C6—C5	1.2 (4)	C11—C12—C13—C14	0.7 (4)
C4—C5—C6—C1	−0.6 (4)	C17—O5—C14—C15	−11.9 (4)
C9—C5—C6—C1	178.5 (2)	C17—O5—C14—C13	167.5 (2)
C4—C5—C6—O1	178.7 (2)	C12—C13—C14—C15	−0.7 (4)
C9—C5—C6—O1	−2.3 (4)	C12—C13—C14—O5	179.8 (2)
C6—O1—C7—O2	−176.5 (2)	O5—C14—C15—C16	179.5 (2)
C6—O1—C7—C8	1.8 (4)	C13—C14—C15—C16	0.1 (4)
O2—C7—C8—C9	174.3 (3)	C12—C11—C16—C15	−0.5 (4)
O1—C7—C8—C9	−3.8 (4)	O4—C11—C16—C15	−174.0 (2)
O2—C7—C8—C10	−8.4 (4)	C14—C15—C16—C11	0.5 (4)
O1—C7—C8—C10	173.6 (2)	C14—O5—C17—C18	178.6 (2)
C7—C8—C9—C5	2.8 (4)	O5—C17—C18—C19	174.9 (2)
C10—C8—C9—C5	−174.5 (2)	C17—C18—C19—C20	175.7 (2)
C6—C5—C9—C8	0.3 (4)	C18—C19—C20—C21	−178.6 (3)
C4—C5—C9—C8	179.2 (3)	C19—C20—C21—C22	−177.7 (3)
C11—O4—C10—O3	−4.6 (4)	C20—C21—C22—C23	180.0 (3)
C11—O4—C10—C8	173.1 (2)	C21—C22—C23—C24	−178.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.93	2.59	3.513 (4)	174
C9—H9···O2i	0.93	2.51	3.420 (3)	167
C16—H16···O2ii	0.93	2.71	3.551 (3)	151
C16—H16···O3ii	0.93	2.63	3.338 (3)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.93	2.59	3.513 (4)	174
C9—H9⋯O2i	0.93	2.51	3.420 (3)	167
C16—H16⋯O2i	0.93	2.71	3.551 (3)	151
C16—H16⋯O3i	0.93	2.63	3.338 (3)	133

Symmetry code: (i) .