1-(2-Fluoro­phen­yl)-6,7-dimethoxy­isochroman

Saeed, A.; Simpson, J.; Stanley, R.G.

doi:10.1107/S160053680900926X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o867-o868

doi:10.1107/S160053680900926X

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1-(2-Fluorophenyl)-6,7-dimethoxyisochroman

Aamer Saeed,^a ^* Jim Simpson ^b and Roderick G. Stanley ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin, New Zealand
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 11 February 2009; accepted 13 March 2009; online 25 March 2009)

In the title compound, C₁₇H₁₇FO₃, the benzene ring of the isochroman unit is inclined at 84.96 (7)° to the fluorobenzene ring plane, and the pyran ring adopts a half-boat conformation. In the crystal structure, C—H⋯O hydrogen bonds link molecules into rows along the c axis, while C—H⋯O interactions and C—H⋯F hydrogen bonds to the fluorine acceptor stack the molecules down the b axis. In addition, the crystal structure exhibits a weak C—H⋯π interaction between a methyl H atom of the methoxy group and the dimethoxybenzene ring of an adjacent molecule.

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_r = 288.31
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.074
wR(F²) = 0.261
S = 1.28
2371 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ . Cg2 is the centroid of the C3–C8 benzene ring.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Isochroman is a common structural motif found in many natural products. For example 1,6,8-trihydroxy-3-heptyl-7-carboxyisochroman, is an antibiotic and topoisomerase II inhibitor from Penicillum sp. (Imamura et al., 2000), pseudodeflectusin is a selective human cancer cytotoxin from Aspergillus pseudodeflectus, (Ogawa et al., 2004), in softwood lignin (Peng et al., 1999) and in the male wing gland pheromone of Aphomia sociella (Kunesch et al., 1987). A novel isochroman derivative inhibited apoptosis in vascular endothelial cells by depressing the levels of integrin 4, p53 and ROS (Zhang et al., 2008). 1-Phenyl- and 1-(3-methoxy-4-hydroxy)phenyl-6,7-dihydroxyisochromans identified in extra-virgin olive oil exhibit beneficial antioxidant effects (Lorenz et al., 2005) and antiplatelet activity (Togna et al., 2003). Isochroman derivatives also show plant-growth regulatory and herbicidal activities (Bianchi et al., 2004; Cutler et al., 1997), these are oestrogen receptors (Liu et al., 2005), dopamine receptor ligands (TenBrink et al., 1996), and fragrances, such as galaxolide (Frater et al., 1999). 1-Aryl-6,7-dimethoxyisochromans are known to demonstrate analgesic, muscle relaxant, antidepressant, antiinflammatory, antihistaminic and anticoagulant activity and are adrenergic antagonists (Dobson & Humber 1975; Yamato et al., 1985; McCall et al., 1982). The title dimethoxyisochroman derivative (I), Fig. 1, was prepared by the oxa-Pictet–Spengler reaction for the preparation of isochromans (Guiso et al., 2001) using 2-(3,4-dimethoxyphenyl)ethanol and 2-fluorobenzaldehyde.

The pyran ring of (I) adopts a half-boat conformation (Cremer & Pople, 1975) with the O1 atom 0.639 (3) Å from the least-squares plane through atoms C1–C3, C8, C9. The r.m.s. deviation from this plane was 0.083 Å. The benzene ring of the isochroman unit is inclined at 84.96 (7) ° to the fluorobenzene ring plane. Both the C and O atoms of the two methoxy substituents lie close to the aromatic ring plane (maximum deviation 0.310 (5) Å for C16).

In the molecular packing (Fig. 2), C17—H17B···O1 hydrogen bonds link the molecules into rows along the c axis (Fig. 2 and Table 1; symmetry codes as in Fig. 2). The F1 atom acts as an acceptor in a C7—H7···F1 hydrogen bond that, together with C1—H1B···O2 interactions, stacks molecules from individual rows down the the b axis (Fig. 2, Fig 3 and Table 1; symmetry codes as in Fig. 2). Additionally, a weak C—H···π interaction in the structure was observed between a methyl H atom of the methoxy group and the dimethoxybenzene ring of an adjacent molecule, with a C17—H17A···Cgⁱ separation of 2.70 Å (Table 1 and Fig. 2; Cg is the centroid of the C3–C8 benzene ring, symmetry codes as in Fig. 2).)

Related literature top

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 top

A homogenized mixture of 2-(3,4-dimethoxyphenyl)ethanol (0.18g, 1 mmol) and 4-fluorobenzaldehyde (0.12g 1 mmol) and a catalytic amount of p-toluenesulfonic acid monohydrate was irradiated for 1.3 min. The product was purified by thin layer chromatography using petroleum ether and ethyl acetate (7:2 v:v) to afford the title compound (0.91 mmol, 91%) which was recrystallized from ethyl acetate. Analysis calculated for C₁₇H₁₇O₃F: C, 70.82%, H, 5.94% found, 70.69%, H, 5.97%.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. C—H···F, C—H···O (dashed lines) and C—H···π interactions (dotted lines) in the title compound. The yellow spheres denote the ring centroids [symmetry codes: (i) x, 1.5-y,-1/2+z; (ii) x, 1+y,z; (iii) x, 1.5-y, 1/2+z; (iv) x, 2.5-y, -1/2+z; (v) x, -1+y, z; (vi) x, 2.5-y, 1/2+z ].
	Fig. 3. Crystal packing for (I) viewed down the b axis with hydrogen bonds drawn as dashed lines and H atoms on atoms not involved in hydrogen bonding omitted.

1-(2-Fluorophenyl)-6,7-dimethoxyisochroman top

Crystal data top

C₁₇H₁₇FO₃	F(000) = 608
M_r = 288.31	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.1483P)² + 0.6898P] where P = (F_o² + 2F_c²)/3
S = 1.28	(Δ/σ)_max < 0.001
2371 reflections	Δρ_max = 0.45 e Å⁻³
193 parameters	Δρ_min = −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)

Crystal data top

C₁₇H₁₇FO₃	V = 1354.3 (3) Å³
M_r = 288.31	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.730 (2) Å	µ = 0.11 mm⁻¹
b = 5.2328 (8) Å	T = 89 K
c = 16.477 (2) Å	0.29 × 0.22 × 0.13 mm
β = 93.108 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2371 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	1864 reflections with I > 2σ(I)
T_min = 0.789, T_max = 0.986	R_int = 0.072
13466 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.261	H-atom parameters constrained
S = 1.28	Δρ_max = 0.45 e Å⁻³
2371 reflections	Δρ_min = −0.37 e Å⁻³
193 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z−1/2; (ii) x, y+1, z; (iii) x, −y+5/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇FO₃
M_r	288.31
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	89
a, b, c (Å)	15.730 (2), 5.2328 (8), 16.477 (2)
β (°)	93.108 (8)
V (Å³)	1354.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.29 × 0.22 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.789, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	13466, 2371, 1864
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.261, 1.28
No. of reflections	2371
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.37

Computer programs: APEX2 (Bruker, 2006), APEX2 and SAINT (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and TITAN (Hunter & Simpson, 1999), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2ⁱ	0.99	2.59	3.360 (5)	134.1
C7—H7···F1ⁱⁱ	0.95	2.45	3.360 (4)	159.8
C17—H17B···O1ⁱⁱⁱ	0.98	2.49	3.430 (4)	159.9
C17—H17A···Cgⁱⁱ	0.98	2.70	3.557 (3)	146.2

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y+1, z; (iii) x, −y+5/2, z+1/2.

Acknowledgements

The authors thank the University of Otago for the purchase of the diffractometer.

References

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