1-(2-Fluoro-phen-yl)-6,7-dimethoxy-isochroman.

In the title compound, C(17)H(17)FO(3), the benzene ring of the isochroman unit is inclined at 84.96 (7)° to the fluoro-benzene ring plane, and the pyran ring adopts a half-boat conformation. In the crystal structure, C-H⋯O hydrogen bonds link mol-ecules into rows along the c axis, while C-H⋯O inter-actions and C-H⋯F hydrogen bonds to the fluorine acceptor stack the mol-ecules down the b axis. In addition, the crystal structure exhibits a weak C-H⋯π inter-action between a methyl H atom of the meth-oxy group and the dimethoxy-benzene ring of an adjacent mol-ecule.

Related literature

For details of naturally occurring isochromans, see: Imamura et al. (2000 ▶); Ogawa et al. (2004 ▶); Peng et al. (1999 ▶); Kunesch et al. (1987 ▶). For the biological activity of isochromans, see: Zhang et al. (2008 ▶); Lorenz et al. (2005 ▶); Togna et al. (2003 ▶); Bianchi et al. (2004 ▶); Cutler et al. (1997 ▶); Liu et al. (2005 ▶); TenBrink et al. (1996 ▶); Frater et al. (1999 ▶); Dobson & Humber (1975 ▶); Yamato et al. (1985 ▶); McCall et al. (1982 ▶). For the synthesis of isochromans, see: Guiso et al. (2001 ▶). For related structures, see: Saeed & Flörke (2006a ▶,b ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶); and for reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H17FO3

M = 288.31

Monoclinic,

a = 15.730 (2) Å

b = 5.2328 (8) Å

c = 16.477 (2) Å

β = 93.108 (8)°

V = 1354.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 89 K

0.29 × 0.22 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.789, T max = 0.986

13466 measured reflections

2371 independent reflections

1864 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.261

S = 1.28

2371 reflections

193 parameters

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900926X/lx2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900926X/lx2092Isup2.hkl

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

C17H17FO3	F(000) = 608
Mr = 288.31	Dx = 1.414 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3061 reflections
a = 15.730 (2) Å	θ = 2.5–28.7°
b = 5.2328 (8) Å	µ = 0.11 mm−1
c = 16.477 (2) Å	T = 89 K
β = 93.108 (8)°	Irregular fragment, colourless
V = 1354.3 (3) Å3	0.29 × 0.22 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2371 independent reflections
Radiation source: fine-focus sealed tube	1864 reflections with I > 2σ(I)
graphite	Rint = 0.072
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 2.6°
ω' scans	h = −17→18
Absorption correction: multi-scan (SADABS; Bruker, 2006)	k = −6→5
Tmin = 0.789, Tmax = 0.986	l = −19→19
13466 measured reflections

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)] = 0.074	H-atom parameters constrained
wR(F2) = 0.261	w = 1/[σ2(Fo2) + (0.1483P)2 + 0.6898P] where P = (Fo2 + 2Fc2)/3
S = 1.28	(Δ/σ)max < 0.001
2371 reflections	Δρmax = 0.45 e Å−3
193 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.021 (8)

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.

	x	y	z	Uiso*/Ueq
O1	0.23025 (15)	0.7414 (5)	0.31621 (15)	0.0181 (7)
C1	0.3182 (2)	0.7001 (7)	0.3030 (2)	0.0203 (9)
H1A	0.3425	0.8551	0.2787	0.024*
H1B	0.3240	0.5568	0.2644	0.024*
C2	0.3667 (2)	0.6388 (7)	0.3826 (2)	0.0177 (9)
H2A	0.3524	0.4635	0.3999	0.021*
H2B	0.4287	0.6455	0.3749	0.021*
C3	0.3445 (2)	0.8270 (7)	0.4478 (2)	0.0151 (8)
C4	0.3972 (2)	0.8448 (6)	0.5191 (2)	0.0149 (8)
H4	0.4458	0.7373	0.5257	0.018*
C5	0.3797 (2)	1.0161 (6)	0.5799 (2)	0.0140 (8)
O2	0.42783 (15)	1.0436 (5)	0.65158 (15)	0.0173 (7)
C16	0.4888 (2)	0.8446 (7)	0.6690 (2)	0.0199 (9)
H16A	0.4608	0.6779	0.6626	0.030*
H16B	0.5124	0.8627	0.7250	0.030*
H16C	0.5348	0.8571	0.6314	0.030*
C6	0.3085 (2)	1.1783 (6)	0.5699 (2)	0.0143 (8)
O3	0.29623 (15)	1.3416 (5)	0.63316 (15)	0.0167 (7)
C17	0.2271 (2)	1.5183 (7)	0.6224 (2)	0.0167 (8)
H17A	0.2353	1.6245	0.5745	0.025*
H17B	0.2251	1.6275	0.6706	0.025*
H17C	0.1734	1.4238	0.6148	0.025*
C7	0.2562 (2)	1.1589 (6)	0.4993 (2)	0.0143 (8)
H7	0.2078	1.2665	0.4922	0.017*
C8	0.2740 (2)	0.9841 (6)	0.4389 (2)	0.0143 (8)
C9	0.2186 (2)	0.9759 (7)	0.3601 (2)	0.0154 (8)
H9	0.2368	1.1196	0.3250	0.019*
C10	0.1238 (2)	1.0018 (6)	0.3687 (2)	0.0146 (8)
C11	0.0776 (2)	0.8291 (6)	0.4129 (2)	0.0145 (8)
F1	0.12090 (13)	0.6419 (4)	0.45485 (12)	0.0202 (6)
C12	−0.0089 (2)	0.8363 (6)	0.4168 (2)	0.0164 (8)
H12	−0.0378	0.7140	0.4479	0.020*
C13	−0.0540 (2)	1.0280 (7)	0.3740 (2)	0.0185 (9)
H13	−0.1142	1.0358	0.3750	0.022*
C14	−0.0104 (2)	1.2076 (7)	0.3300 (2)	0.0193 (9)
H14	−0.0409	1.3394	0.3014	0.023*
C15	0.0770 (2)	1.1947 (7)	0.3276 (2)	0.0162 (8)
H15	0.1061	1.3190	0.2975	0.019*

	U11	U22	U33	U12	U13	U23
O1	0.0232 (14)	0.0159 (14)	0.0156 (14)	−0.0003 (10)	0.0048 (10)	−0.0068 (11)
C1	0.0219 (19)	0.021 (2)	0.018 (2)	0.0006 (15)	0.0063 (14)	−0.0041 (16)
C2	0.0219 (19)	0.0131 (18)	0.019 (2)	−0.0007 (14)	0.0067 (14)	−0.0015 (15)
C3	0.0200 (18)	0.0126 (18)	0.0135 (19)	−0.0019 (13)	0.0069 (13)	0.0019 (14)
C4	0.0190 (18)	0.0121 (18)	0.0139 (19)	0.0019 (13)	0.0034 (13)	0.0016 (14)
C5	0.0183 (18)	0.0131 (17)	0.0106 (18)	−0.0022 (13)	0.0020 (13)	0.0020 (14)
O2	0.0204 (13)	0.0169 (13)	0.0145 (14)	0.0043 (10)	−0.0012 (9)	−0.0007 (11)
C16	0.0218 (19)	0.0155 (19)	0.022 (2)	0.0026 (14)	−0.0017 (14)	0.0030 (16)
C6	0.0232 (19)	0.0093 (17)	0.0111 (18)	−0.0017 (13)	0.0061 (13)	−0.0018 (13)
O3	0.0233 (14)	0.0151 (14)	0.0116 (13)	0.0065 (10)	−0.0012 (9)	−0.0042 (10)
C17	0.0215 (18)	0.0127 (18)	0.0159 (19)	0.0030 (14)	0.0013 (13)	−0.0051 (14)
C7	0.0188 (18)	0.0094 (17)	0.0148 (19)	0.0014 (13)	0.0023 (13)	0.0026 (14)
C8	0.0222 (19)	0.0108 (17)	0.0104 (18)	−0.0027 (13)	0.0047 (13)	0.0012 (14)
C9	0.0247 (19)	0.0114 (17)	0.0105 (18)	−0.0005 (14)	0.0040 (13)	−0.0022 (14)
C10	0.0238 (19)	0.0103 (17)	0.0096 (18)	−0.0011 (13)	0.0004 (13)	−0.0041 (14)
C11	0.026 (2)	0.0077 (17)	0.0091 (18)	0.0035 (13)	−0.0024 (13)	−0.0006 (13)
F1	0.0249 (12)	0.0154 (12)	0.0202 (12)	0.0025 (8)	0.0001 (8)	0.0071 (9)
C12	0.029 (2)	0.0109 (18)	0.0099 (19)	−0.0009 (14)	0.0029 (14)	−0.0023 (14)
C13	0.0215 (19)	0.0170 (19)	0.0169 (19)	0.0021 (14)	0.0009 (14)	−0.0038 (15)
C14	0.030 (2)	0.0125 (18)	0.0148 (19)	0.0064 (14)	−0.0032 (14)	−0.0016 (15)
C15	0.031 (2)	0.0090 (16)	0.0085 (18)	−0.0008 (14)	0.0011 (13)	0.0015 (13)

O1—C1	1.429 (4)	O3—C17	1.432 (4)
O1—C9	1.441 (4)	C17—H17A	0.9800
C1—C2	1.516 (5)	C17—H17B	0.9800
C1—H1A	0.9900	C17—H17C	0.9800
C1—H1B	0.9900	C7—C8	1.391 (5)
C2—C3	1.512 (5)	C7—H7	0.9500
C2—H2A	0.9900	C8—C9	1.525 (5)
C2—H2B	0.9900	C9—C10	1.511 (5)
C3—C8	1.382 (5)	C9—H9	1.0000
C3—C4	1.404 (5)	C10—C11	1.391 (5)
C4—C5	1.384 (5)	C10—C15	1.401 (5)
C4—H4	0.9500	C11—F1	1.360 (4)
C5—O2	1.375 (4)	C11—C12	1.367 (5)
C5—C6	1.408 (5)	C12—C13	1.397 (5)
O2—C16	1.434 (4)	C12—H12	0.9500
C16—H16A	0.9800	C13—C14	1.391 (6)
C16—H16B	0.9800	C13—H13	0.9500
C16—H16C	0.9800	C14—C15	1.379 (5)
C6—O3	1.370 (4)	C14—H14	0.9500
C6—C7	1.391 (5)	C15—H15	0.9500
C1—O1—C9	110.9 (3)	H17A—C17—H17B	109.5
O1—C1—C2	110.2 (3)	O3—C17—H17C	109.5
O1—C1—H1A	109.6	H17A—C17—H17C	109.5
C2—C1—H1A	109.6	H17B—C17—H17C	109.5
O1—C1—H1B	109.6	C6—C7—C8	120.9 (3)
C2—C1—H1B	109.6	C6—C7—H7	119.5
H1A—C1—H1B	108.1	C8—C7—H7	119.5
C3—C2—C1	110.6 (3)	C3—C8—C7	120.4 (3)
C3—C2—H2A	109.5	C3—C8—C9	119.5 (3)
C1—C2—H2A	109.5	C7—C8—C9	120.0 (3)
C3—C2—H2B	109.5	O1—C9—C10	106.1 (3)
C1—C2—H2B	109.5	O1—C9—C8	111.6 (3)
H2A—C2—H2B	108.1	C10—C9—C8	116.0 (3)
C8—C3—C4	118.9 (3)	O1—C9—H9	107.6
C8—C3—C2	121.8 (3)	C10—C9—H9	107.6
C4—C3—C2	119.3 (3)	C8—C9—H9	107.6
C5—C4—C3	121.2 (3)	C11—C10—C15	116.5 (3)
C5—C4—H4	119.4	C11—C10—C9	122.5 (3)
C3—C4—H4	119.4	C15—C10—C9	120.9 (3)
O2—C5—C4	124.6 (3)	F1—C11—C12	117.9 (3)
O2—C5—C6	115.8 (3)	F1—C11—C10	118.2 (3)
C4—C5—C6	119.6 (3)	C12—C11—C10	123.8 (3)
C5—O2—C16	115.3 (3)	C11—C12—C13	118.4 (3)
O2—C16—H16A	109.5	C11—C12—H12	120.8
O2—C16—H16B	109.5	C13—C12—H12	120.8
H16A—C16—H16B	109.5	C14—C13—C12	119.9 (3)
O2—C16—H16C	109.5	C14—C13—H13	120.1
H16A—C16—H16C	109.5	C12—C13—H13	120.1
H16B—C16—H16C	109.5	C15—C14—C13	120.1 (3)
O3—C6—C7	125.5 (3)	C15—C14—H14	119.9
O3—C6—C5	115.5 (3)	C13—C14—H14	119.9
C7—C6—C5	119.0 (3)	C14—C15—C10	121.3 (3)
C6—O3—C17	116.5 (3)	C14—C15—H15	119.4
O3—C17—H17A	109.5	C10—C15—H15	119.4
O3—C17—H17B	109.5
C9—O1—C1—C2	69.6 (4)	C6—C7—C8—C9	−176.7 (3)
O1—C1—C2—C3	−47.7 (4)	C1—O1—C9—C10	178.8 (3)
C1—C2—C3—C8	15.5 (5)	C1—O1—C9—C8	−54.0 (4)
C1—C2—C3—C4	−164.0 (3)	C3—C8—C9—O1	20.5 (4)
C8—C3—C4—C5	−0.1 (5)	C7—C8—C9—O1	−163.2 (3)
C2—C3—C4—C5	179.4 (3)	C3—C8—C9—C10	142.2 (3)
C3—C4—C5—O2	179.5 (3)	C7—C8—C9—C10	−41.5 (4)
C3—C4—C5—C6	−0.9 (5)	O1—C9—C10—C11	64.0 (4)
C4—C5—O2—C16	−13.0 (5)	C8—C9—C10—C11	−60.5 (4)
C6—C5—O2—C16	167.4 (3)	O1—C9—C10—C15	−111.9 (3)
O2—C5—C6—O3	−0.4 (4)	C8—C9—C10—C15	123.6 (3)
C4—C5—C6—O3	−179.9 (3)	C15—C10—C11—F1	−178.8 (3)
O2—C5—C6—C7	−179.2 (3)	C9—C10—C11—F1	5.1 (5)
C4—C5—C6—C7	1.2 (5)	C15—C10—C11—C12	1.1 (5)
C7—C6—O3—C17	−4.7 (5)	C9—C10—C11—C12	−174.9 (3)
C5—C6—O3—C17	176.6 (3)	F1—C11—C12—C13	179.9 (3)
O3—C6—C7—C8	−179.3 (3)	C10—C11—C12—C13	0.0 (5)
C5—C6—C7—C8	−0.6 (5)	C11—C12—C13—C14	−1.0 (5)
C4—C3—C8—C7	0.8 (5)	C12—C13—C14—C15	0.8 (5)
C2—C3—C8—C7	−178.7 (3)	C13—C14—C15—C10	0.3 (5)
C4—C3—C8—C9	177.1 (3)	C11—C10—C15—C14	−1.3 (5)
C2—C3—C8—C9	−2.4 (5)	C9—C10—C15—C14	174.8 (3)
C6—C7—C8—C3	−0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.99	2.59	3.360 (5)	134
C7—H7···F1ii	0.95	2.45	3.360 (4)	160
C17—H17B···O1iii	0.98	2.49	3.430 (4)	160
C17—H17A···Cgii	0.98	2.70	3.557 (3)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2i	0.99	2.59	3.360 (5)	134
C7—H7⋯F1ii	0.95	2.45	3.360 (4)	160
C17—H17B⋯O1iii	0.98	2.49	3.430 (4)	160
C17—H17A⋯Cgii	0.98	2.70	3.557 (3)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 is the centroid of the C3–C8 benzene ring.