3-(4-Methoxy-phen-yl)-1H-isochromen-1-one.

The asymmetric unit of the title compound, C(16)H(12)O(3), contains two crystallographically independent mol-ecules. The isochromene ring system is planar (maximum deviation 0.024 Å) and is oriented at dihedral angles of 2.63 (3) and 0.79 (3)° with respect to the methoxy-benzene rings in the two independent mol-ecules.

Related literature

For general background, see: Barry (1964 ▶); Hill (1986 ▶); Canendo et al. (1997 ▶); Whyte et al. (1996 ▶). For related structures, see: Abid et al. (2006 ▶, 2008 ▶); Hathwar et al. (2007 ▶).

Experimental

Crystal data

C16H12O3

M = 252.26

Monoclinic,

a = 15.5949 (15) Å

b = 11.8464 (11) Å

c = 15.1824 (14) Å

β = 117.838 (2)°

V = 2480.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 290 (2) K

0.28 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.974, T max = 0.984

18262 measured reflections

4616 independent reflections

2795 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.109

S = 1.00

4616 reflections

345 parameters

All H-atom parameters refined

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808042074/nc2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042074/nc2128Isup2.hkl

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

C16H12O3	F(000) = 1056
Mr = 252.26	Dx = 1.351 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8668 reflections
a = 15.5949 (15) Å	θ = 1.5–25.5°
b = 11.8464 (11) Å	µ = 0.09 mm−1
c = 15.1824 (14) Å	T = 290 K
β = 117.838 (2)°	Block, colourless
V = 2480.2 (4) Å3	0.28 × 0.14 × 0.08 mm
Z = 8

Bruker SMART CCD area-detector diffractometer	4616 independent reflections
Radiation source: fine-focus sealed tube	2795 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.974, Tmax = 0.984	k = −13→14
18262 measured reflections	l = −18→18

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	All H-atom parameters refined
S = 1.00	w = 1/[σ2(Fo2) + (0.0567P)2] where P = (Fo2 + 2Fc2)/3
4616 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.15 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.

	x	y	z	Uiso*/Ueq
O1	0.46573 (12)	0.71997 (11)	1.12417 (10)	0.0894 (5)
O2	0.41915 (8)	0.88630 (10)	1.05390 (8)	0.0602 (3)
O3	0.35416 (9)	1.40912 (10)	1.06979 (10)	0.0762 (4)
O4	0.03964 (12)	0.71696 (11)	0.15948 (11)	0.0912 (5)
O5	0.08196 (8)	0.88474 (10)	0.13156 (8)	0.0595 (3)
O6	0.13583 (9)	1.40934 (10)	0.20493 (9)	0.0667 (4)
C1	0.43111 (14)	0.77173 (16)	1.04693 (14)	0.0606 (5)
C2	0.38013 (11)	0.95680 (14)	0.97170 (12)	0.0470 (4)
C3	0.35328 (11)	0.91498 (14)	0.88124 (12)	0.0496 (4)
H3	0.3276	0.9634	0.8267	0.060*
C4	0.33679 (13)	0.75059 (16)	0.77199 (13)	0.0600 (5)
H4	0.3121	0.7967	0.7159	0.072*
C5	0.34738 (13)	0.63695 (17)	0.76232 (14)	0.0667 (5)
H5	0.3305	0.6069	0.6998	0.080*
C6	0.38271 (13)	0.56691 (17)	0.84417 (15)	0.0690 (5)
H6	0.3885	0.4899	0.8364	0.083*
C7	0.40934 (13)	0.61035 (16)	0.93675 (14)	0.0646 (5)
H7	0.4332	0.5630	0.9920	0.077*
C8	0.40056 (12)	0.72591 (15)	0.94798 (12)	0.0503 (4)
C9	0.36294 (11)	0.79755 (14)	0.86563 (12)	0.0475 (4)
C10	0.37489 (11)	1.07382 (14)	1.00008 (12)	0.0467 (4)
C11	0.40524 (12)	1.10565 (15)	1.09812 (12)	0.0551 (5)
H11	0.4297	1.0508	1.1476	0.066*
C12	0.40041 (13)	1.21545 (16)	1.12477 (13)	0.0581 (5)
H12	0.4221	1.2340	1.1913	0.070*
C13	0.36364 (13)	1.29749 (15)	1.05313 (14)	0.0552 (5)
C14	0.33210 (13)	1.26874 (16)	0.95395 (14)	0.0629 (5)
H14	0.3067	1.3238	0.9047	0.076*
C15	0.33854 (13)	1.15925 (15)	0.92883 (13)	0.0593 (5)
H15	0.3181	1.1414	0.8623	0.071*
C16	0.38761 (16)	1.44487 (18)	1.16989 (16)	0.0882 (7)
H16A	0.3474	1.4126	1.1956	0.132*
H16B	0.3846	1.5257	1.1720	0.132*
H16C	0.4534	1.4205	1.2096	0.132*
C17	0.07336 (13)	0.77001 (16)	0.11542 (13)	0.0607 (5)
C18	0.11848 (11)	0.95659 (14)	0.08575 (11)	0.0473 (4)
C19	0.14586 (11)	0.91583 (14)	0.02099 (12)	0.0507 (4)
H19	0.1691	0.9653	−0.0105	0.061*
C20	0.16909 (13)	0.75191 (15)	−0.06827 (14)	0.0608 (5)
H20	0.1914	0.7993	−0.1020	0.073*
C21	0.16469 (14)	0.63793 (17)	−0.08482 (14)	0.0690 (5)
H21	0.1846	0.6087	−0.1292	0.083*
C22	0.13085 (14)	0.56579 (17)	−0.03610 (14)	0.0713 (6)
H22	0.1281	0.4884	−0.0476	0.086*
C23	0.10135 (13)	0.60905 (16)	0.02928 (14)	0.0664 (5)
H23	0.0785	0.5609	0.0620	0.080*
C24	0.10552 (12)	0.72472 (15)	0.04675 (12)	0.0510 (4)
C25	0.14046 (11)	0.79797 (14)	−0.00148 (12)	0.0477 (4)
C26	0.12307 (11)	1.07354 (14)	0.11878 (11)	0.0471 (4)
C27	0.09425 (12)	1.10360 (15)	0.18924 (12)	0.0575 (5)
H27	0.0723	1.0476	0.2167	0.069*
C28	0.09700 (13)	1.21374 (15)	0.22010 (13)	0.0584 (5)
H28	0.0772	1.2312	0.2675	0.070*
C29	0.12929 (12)	1.29732 (15)	0.18019 (13)	0.0517 (5)
C30	0.15888 (13)	1.26986 (15)	0.10993 (14)	0.0621 (5)
H30	0.1811	1.3261	0.0829	0.074*
C31	0.15544 (13)	1.16016 (15)	0.08009 (13)	0.0595 (5)
H31	0.1753	1.1432	0.0326	0.071*
C32	0.09712 (14)	1.44297 (16)	0.26951 (14)	0.0770 (6)
H32A	0.0317	1.4163	0.2434	0.115*
H32B	0.0979	1.5238	0.2741	0.115*
H32C	0.1358	1.4114	0.3345	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.1390 (14)	0.0681 (9)	0.0507 (8)	0.0230 (9)	0.0355 (9)	0.0148 (7)
O2	0.0798 (9)	0.0542 (8)	0.0436 (7)	0.0102 (6)	0.0262 (6)	0.0041 (6)
O3	0.0977 (11)	0.0546 (9)	0.0764 (10)	0.0029 (7)	0.0407 (8)	−0.0108 (7)
O4	0.1466 (14)	0.0660 (9)	0.1082 (11)	−0.0176 (9)	0.0991 (11)	−0.0002 (8)
O5	0.0785 (9)	0.0537 (8)	0.0633 (8)	−0.0091 (6)	0.0473 (7)	−0.0027 (6)
O6	0.0808 (9)	0.0559 (9)	0.0723 (9)	−0.0028 (7)	0.0431 (7)	−0.0091 (7)
C1	0.0737 (14)	0.0577 (13)	0.0510 (12)	0.0102 (10)	0.0295 (11)	0.0063 (10)
C2	0.0468 (10)	0.0532 (12)	0.0422 (10)	0.0010 (8)	0.0216 (8)	0.0069 (9)
C3	0.0550 (11)	0.0513 (12)	0.0421 (10)	0.0013 (8)	0.0222 (9)	0.0070 (8)
C4	0.0612 (13)	0.0649 (14)	0.0481 (11)	−0.0035 (10)	0.0207 (10)	−0.0031 (9)
C5	0.0642 (13)	0.0718 (15)	0.0568 (13)	−0.0066 (11)	0.0220 (11)	−0.0176 (11)
C6	0.0734 (14)	0.0573 (13)	0.0729 (14)	0.0018 (10)	0.0313 (12)	−0.0088 (11)
C7	0.0747 (14)	0.0571 (14)	0.0642 (13)	0.0108 (10)	0.0343 (11)	0.0048 (10)
C8	0.0505 (11)	0.0533 (12)	0.0491 (11)	0.0024 (9)	0.0249 (9)	0.0002 (9)
C9	0.0424 (10)	0.0560 (12)	0.0446 (11)	−0.0041 (8)	0.0208 (9)	−0.0018 (9)
C10	0.0425 (10)	0.0514 (11)	0.0458 (10)	−0.0009 (8)	0.0203 (8)	0.0010 (9)
C11	0.0613 (12)	0.0582 (13)	0.0469 (11)	0.0034 (9)	0.0261 (9)	0.0023 (9)
C12	0.0663 (13)	0.0611 (13)	0.0477 (11)	0.0006 (10)	0.0271 (10)	−0.0052 (10)
C13	0.0554 (12)	0.0506 (13)	0.0622 (13)	−0.0029 (9)	0.0296 (10)	−0.0074 (10)
C14	0.0723 (14)	0.0546 (13)	0.0527 (12)	0.0058 (10)	0.0215 (10)	0.0072 (10)
C15	0.0704 (13)	0.0562 (13)	0.0458 (11)	0.0014 (10)	0.0226 (10)	−0.0015 (9)
C16	0.1071 (18)	0.0744 (16)	0.0891 (16)	−0.0108 (13)	0.0508 (14)	−0.0317 (13)
C17	0.0746 (14)	0.0555 (13)	0.0621 (12)	−0.0061 (10)	0.0404 (11)	0.0017 (10)
C18	0.0462 (10)	0.0534 (12)	0.0451 (10)	−0.0041 (8)	0.0236 (9)	0.0041 (8)
C19	0.0535 (11)	0.0532 (12)	0.0514 (10)	−0.0030 (8)	0.0296 (9)	0.0036 (9)
C20	0.0659 (13)	0.0609 (14)	0.0676 (12)	−0.0032 (10)	0.0413 (11)	−0.0041 (10)
C21	0.0744 (14)	0.0692 (14)	0.0755 (14)	0.0024 (11)	0.0451 (12)	−0.0095 (11)
C22	0.0824 (15)	0.0551 (13)	0.0783 (14)	0.0029 (10)	0.0391 (12)	−0.0053 (11)
C23	0.0775 (14)	0.0581 (14)	0.0695 (13)	−0.0065 (10)	0.0393 (11)	−0.0005 (10)
C24	0.0512 (11)	0.0520 (12)	0.0501 (10)	−0.0006 (9)	0.0237 (9)	−0.0003 (9)
C25	0.0428 (10)	0.0552 (12)	0.0444 (10)	0.0001 (8)	0.0198 (9)	0.0005 (9)
C26	0.0442 (10)	0.0524 (11)	0.0453 (10)	−0.0005 (8)	0.0213 (8)	0.0017 (8)
C27	0.0646 (12)	0.0618 (13)	0.0562 (11)	−0.0057 (9)	0.0365 (10)	0.0009 (9)
C28	0.0684 (13)	0.0622 (13)	0.0551 (11)	−0.0019 (10)	0.0377 (10)	−0.0064 (10)
C29	0.0519 (11)	0.0509 (12)	0.0523 (11)	0.0009 (9)	0.0243 (9)	−0.0022 (9)
C30	0.0728 (14)	0.0543 (12)	0.0749 (13)	−0.0098 (10)	0.0478 (12)	−0.0024 (10)
C31	0.0731 (13)	0.0595 (13)	0.0634 (12)	−0.0060 (10)	0.0465 (11)	−0.0055 (10)
C32	0.0862 (15)	0.0708 (15)	0.0819 (14)	0.0036 (11)	0.0459 (13)	−0.0175 (11)

O1—C1	1.2048 (19)	C14—H14	0.9300
O2—C1	1.381 (2)	C15—H15	0.9300
O2—C2	1.3842 (18)	C16—H16A	0.9600
O3—C13	1.3672 (19)	C16—H16B	0.9600
O3—C16	1.422 (2)	C16—H16C	0.9600
O4—C17	1.2032 (19)	C17—C24	1.454 (2)
O5—C17	1.3765 (19)	C18—C19	1.332 (2)
O5—C18	1.3794 (17)	C18—C26	1.464 (2)
O6—C29	1.3700 (18)	C19—C25	1.431 (2)
O6—C32	1.4272 (19)	C19—H19	0.9300
C1—C8	1.453 (2)	C20—C21	1.369 (2)
C2—C3	1.330 (2)	C20—C25	1.396 (2)
C2—C10	1.465 (2)	C20—H20	0.9300
C3—C9	1.431 (2)	C21—C22	1.386 (3)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.373 (2)	C22—C23	1.373 (2)
C4—C9	1.398 (2)	C22—H22	0.9300
C4—H4	0.9300	C23—C24	1.391 (2)
C5—C6	1.377 (2)	C23—H23	0.9300
C5—H5	0.9300	C24—C25	1.400 (2)
C6—C7	1.367 (2)	C26—C27	1.387 (2)
C6—H6	0.9300	C26—C31	1.389 (2)
C7—C8	1.394 (2)	C27—C28	1.380 (2)
C7—H7	0.9300	C27—H27	0.9300
C8—C9	1.394 (2)	C28—C29	1.373 (2)
C10—C11	1.387 (2)	C28—H28	0.9300
C10—C15	1.394 (2)	C29—C30	1.384 (2)
C11—C12	1.375 (2)	C30—C31	1.369 (2)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.369 (2)	C31—H31	0.9300
C12—H12	0.9300	C32—H32A	0.9600
C13—C14	1.391 (2)	C32—H32B	0.9600
C14—C15	1.369 (2)	C32—H32C	0.9600
C1—O2—C2	122.83 (14)	H16A—C16—H16C	109.5
C13—O3—C16	117.94 (15)	H16B—C16—H16C	109.5
C17—O5—C18	123.25 (13)	O4—C17—O5	116.63 (16)
C29—O6—C32	117.23 (14)	O4—C17—C24	126.34 (18)
O1—C1—O2	116.16 (16)	O5—C17—C24	117.03 (15)
O1—C1—C8	126.72 (19)	C19—C18—O5	119.92 (15)
O2—C1—C8	117.12 (16)	C19—C18—C26	127.93 (15)
C3—C2—O2	120.00 (16)	O5—C18—C26	112.14 (13)
C3—C2—C10	128.46 (16)	C18—C19—C25	121.77 (15)
O2—C2—C10	111.54 (14)	C18—C19—H19	119.1
C2—C3—C9	121.76 (16)	C25—C19—H19	119.1
C2—C3—H3	119.1	C21—C20—C25	120.88 (17)
C9—C3—H3	119.1	C21—C20—H20	119.6
C5—C4—C9	120.42 (17)	C25—C20—H20	119.6
C5—C4—H4	119.8	C20—C21—C22	120.60 (18)
C9—C4—H4	119.8	C20—C21—H21	119.7
C4—C5—C6	120.79 (18)	C22—C21—H21	119.7
C4—C5—H5	119.6	C23—C22—C21	119.68 (19)
C6—C5—H5	119.6	C23—C22—H22	120.2
C7—C6—C5	120.17 (19)	C21—C22—H22	120.2
C7—C6—H6	119.9	C22—C23—C24	120.24 (18)
C5—C6—H6	119.9	C22—C23—H23	119.9
C6—C7—C8	119.70 (18)	C24—C23—H23	119.9
C6—C7—H7	120.2	C23—C24—C25	120.39 (16)
C8—C7—H7	120.2	C23—C24—C17	119.93 (16)
C9—C8—C7	120.83 (16)	C25—C24—C17	119.69 (17)
C9—C8—C1	119.83 (17)	C20—C25—C24	118.20 (16)
C7—C8—C1	119.34 (17)	C20—C25—C19	123.49 (15)
C8—C9—C4	118.06 (16)	C24—C25—C19	118.31 (15)
C8—C9—C3	118.44 (15)	C27—C26—C31	116.70 (16)
C4—C9—C3	123.50 (16)	C27—C26—C18	121.72 (15)
C11—C10—C15	116.53 (16)	C31—C26—C18	121.58 (14)
C11—C10—C2	122.33 (16)	C28—C27—C26	122.33 (16)
C15—C10—C2	121.13 (15)	C28—C27—H27	118.8
C12—C11—C10	122.34 (17)	C26—C27—H27	118.8
C12—C11—H11	118.8	C29—C28—C27	119.43 (16)
C10—C11—H11	118.8	C29—C28—H28	120.3
C13—C12—C11	119.88 (17)	C27—C28—H28	120.3
C13—C12—H12	120.1	O6—C29—C28	124.97 (16)
C11—C12—H12	120.1	O6—C29—C30	115.46 (16)
O3—C13—C12	125.53 (17)	C28—C29—C30	119.57 (17)
O3—C13—C14	115.03 (17)	C31—C30—C29	120.16 (17)
C12—C13—C14	119.44 (17)	C31—C30—H30	119.9
C15—C14—C13	119.93 (17)	C29—C30—H30	119.9
C15—C14—H14	120.0	C30—C31—C26	121.81 (16)
C13—C14—H14	120.0	C30—C31—H31	119.1
C14—C15—C10	121.87 (16)	C26—C31—H31	119.1
C14—C15—H15	119.1	O6—C32—H32A	109.5
C10—C15—H15	119.1	O6—C32—H32B	109.5
O3—C16—H16A	109.5	H32A—C32—H32B	109.5
O3—C16—H16B	109.5	O6—C32—H32C	109.5
H16A—C16—H16B	109.5	H32A—C32—H32C	109.5
O3—C16—H16C	109.5	H32B—C32—H32C	109.5
C2—O2—C1—O1	−179.82 (16)	C18—O5—C17—O4	−179.43 (17)
C2—O2—C1—C8	−0.1 (2)	C18—O5—C17—C24	0.4 (2)
C1—O2—C2—C3	−0.7 (2)	C17—O5—C18—C19	1.2 (2)
C1—O2—C2—C10	179.49 (14)	C17—O5—C18—C26	−177.86 (14)
O2—C2—C3—C9	0.4 (2)	O5—C18—C19—C25	−1.3 (2)
C10—C2—C3—C9	−179.86 (14)	C26—C18—C19—C25	177.58 (15)
C9—C4—C5—C6	0.8 (3)	C25—C20—C21—C22	0.6 (3)
C4—C5—C6—C7	−1.1 (3)	C20—C21—C22—C23	0.1 (3)
C5—C6—C7—C8	0.0 (3)	C21—C22—C23—C24	−0.1 (3)
C6—C7—C8—C9	1.4 (3)	C22—C23—C24—C25	−0.5 (3)
C6—C7—C8—C1	−178.60 (17)	C22—C23—C24—C17	179.46 (17)
O1—C1—C8—C9	−179.05 (18)	O4—C17—C24—C23	−2.0 (3)
O2—C1—C8—C9	1.3 (2)	O5—C17—C24—C23	178.20 (15)
O1—C1—C8—C7	1.0 (3)	O4—C17—C24—C25	177.94 (19)
O2—C1—C8—C7	−178.74 (15)	O5—C17—C24—C25	−1.9 (2)
C7—C8—C9—C4	−1.7 (2)	C21—C20—C25—C24	−1.1 (3)
C1—C8—C9—C4	178.31 (15)	C21—C20—C25—C19	178.23 (16)
C7—C8—C9—C3	178.43 (14)	C23—C24—C25—C20	1.1 (2)
C1—C8—C9—C3	−1.6 (2)	C17—C24—C25—C20	−178.86 (15)
C5—C4—C9—C8	0.6 (2)	C23—C24—C25—C19	−178.30 (15)
C5—C4—C9—C3	−179.54 (16)	C17—C24—C25—C19	1.8 (2)
C2—C3—C9—C8	0.7 (2)	C18—C19—C25—C20	−179.51 (16)
C2—C3—C9—C4	−179.12 (16)	C18—C19—C25—C24	−0.2 (2)
C3—C2—C10—C11	179.61 (16)	C19—C18—C26—C27	−178.18 (17)
O2—C2—C10—C11	−0.6 (2)	O5—C18—C26—C27	0.8 (2)
C3—C2—C10—C15	−0.3 (3)	C19—C18—C26—C31	2.6 (3)
O2—C2—C10—C15	179.50 (14)	O5—C18—C26—C31	−178.40 (15)
C15—C10—C11—C12	−0.2 (2)	C31—C26—C27—C28	0.1 (3)
C2—C10—C11—C12	179.95 (15)	C18—C26—C27—C28	−179.13 (15)
C10—C11—C12—C13	0.7 (3)	C26—C27—C28—C29	0.0 (3)
C16—O3—C13—C12	2.0 (3)	C32—O6—C29—C28	−6.6 (2)
C16—O3—C13—C14	−178.23 (17)	C32—O6—C29—C30	173.92 (16)
C11—C12—C13—O3	179.38 (15)	C27—C28—C29—O6	−179.69 (15)
C11—C12—C13—C14	−0.4 (3)	C27—C28—C29—C30	−0.2 (3)
O3—C13—C14—C15	179.79 (16)	O6—C29—C30—C31	179.88 (15)
C12—C13—C14—C15	−0.4 (3)	C28—C29—C30—C31	0.4 (3)
C13—C14—C15—C10	0.9 (3)	C29—C30—C31—C26	−0.3 (3)
C11—C10—C15—C14	−0.7 (3)	C27—C26—C31—C30	0.0 (3)
C2—C10—C15—C14	179.22 (15)	C18—C26—C31—C30	179.28 (16)