2-Meth­oxy-3,4-diphenyl­phenol

Guzei, I.A.; Annamalai, S.; Zimmerman, H.E.

doi:10.1107/S1600536809050855

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o72

doi:10.1107/S1600536809050855

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2-Methoxy-3,4-diphenylphenol

Ilia A. Guzei,^a ^* Senthilvelan Annamalai ^a and Howard E. Zimmerman ^a

^aDepartment of Chemistry, University of Wisconsin-Madison, 1101 University Ave, Madison, WI 53706, USA
^*Correspondence e-mail: iguzei@chem.wisc.edu

(Received 12 November 2009; accepted 25 November 2009; online 9 December 2009)

The title compound, C₁₉H₁₆O₂, was isolated as the major product after the solid-state photochemical reaction of 2-methoxy-4,4-diphenylcyclohexa-2,5-dienone. The dihedral angles between the central ring and pendant benzene rings are 60.76 (6) and 51.64 (6)°. The O—C vector of the methoxy group is almost perpendicular to the plane of the central ring as indicated by the C—C—O—C torsion angle of 94.89 (18)°. Hydrogen-bonded dimers are formed in the crystal structure via O—H⋯O interactions. The data were collected at room temperature on a Bruker SMART X2S diffractometer in the automated mode and processed manually thereafter.

Related literature

For the characterization of reaction products, see: Frimer et al. (1994 ); Matoba et al. (1985 ). Mogul (Bruno et al., 2002 ) was used for the geometrical analysis.

Experimental

Crystal data

C₁₉H₁₆O₂
M_r = 276.32
Monoclinic, P 2₁ /c
a = 14.312 (3) Å
b = 6.2585 (14) Å
c = 17.167 (4) Å
β = 102.930 (7)°
V = 1498.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 300 K
0.36 × 0.30 × 0.28 mm

Data collection

Bruker SMART X2S diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.972, T_max = 0.978
13658 measured reflections
2645 independent reflections
1897 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.129
S = 1.01
2645 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	2.21	2.9043 (18)	142
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: GIS (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL and OLEX2 (Dolomanov et al., 2009 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: local programs (Guzei, 2007 ) and publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050855/tk2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050855/tk2575Isup2.hkl

checkCIF report

Comment top

The title compound (I), Fig. 1, was isolated as the major product during our studies of the solid state photochemical behavior of 2-methoxy-4,4-diphenyl-2,5-cyclohexadienone as described in the Experimental.

All bond distances and angles in (I) fall in the expected ranges according to the Mogul structural check (Bruno, et al., 2002). The dihedral angles between the C1—C6 ring and rings C8—C13 and C14—C19 are 60.76 (6)° and 51.64 (6)°, respectively. The O1—C7 vector of the methoxy group is almost perpendicular to the plane of the C1—C6 ring as indicated by the dihedral angle C2—C1—O1—C7 of 94.89 (18)°. Compound (I) forms hydrogen-bonded dimers in the solid state. The graph set notation for the dimers connected by O2—H2···O1 hydrogen bonds is R₂²(10).

Related literature top

For the characterization of reaction products, see: Frimer et al. (1994); Matoba et al. (1985). Mogul (Bruno et al., 2002) was used for the geometrical analysis.

Experimental top

Solid state photolysis of 2-methoxy-4,4-diphenyl-2,5-cyclohexadienone (II) was studied as follows.

A thin film of (II) (0.30 g, 0.001 mol) was irradiated under nitrogen for 18 h through a CuSO₄ filter with a 400 watt medium pressure mercury lamp. The lamp was surrounded by a water-cooled immersion jacket and a cylindrical flask. The film of (II) was deposited on the inner wall of the outer flask (4 cm from the lamp) by slow evaporation of its dichloromethane solution and was dried before photolysis under nitrogen for 2 h. The resulting orange solid was chromatographed (silica gel 2.5 cm x 37 cm), eluted with hexane-CH₂Cl₂ (2:3) to give the following: band 1, 2-methoxy-4,5-diphenylphenol (III); band 2, 2-methoxy-3,4-diphenylphenol (I), band 3, 6-methoxy-5,6-diphenyl-2,4-cyclohexadienone (IV). The unreacted (band 4) cyclohexadienone (II) (0.10 g, 33%) was separated by using CH₂Cl₂—CH₃OH (9:1) elution (Scheme 1).

2-Methoxy-4,5-diphenylphenol (III) (Band 1): Recrystallization from ether-hexane gave (75 mg, 25%) colorless crystals, mp 419–421 K (Literature mp 422–423 K (Frimer et al., 1994)). ¹H NMR (CDCl₃, 300 MHz): δ 3.95 (s, 3H), 5.62 (s, 1H), 6.91 (s, 1H), 7.02 (s, 1H), 7.10–7.21 (m, 10H) p.p.m.; ¹³C NMR (CDCl₃, 75 MHz) δ 56.3, 113.3, 116.9, 126.4, 128.0, 128.1, 130.2, 130.2, 133.3, 134.1, 141.6, 142.0, 145.1, 146.1 p.p.m.

2-Methoxy-3,4-diphenylphenol (I) (Band 2): Recrystallization from CH₂Cl₂-hexane gave (90 mg, 30%) colorless crystals, mp 417–419 K. ¹H NMR (CDCl₃, 300 MHz): δ 3.29 (s, 3H), 5.88 (s, 1H), 6.99–7.04 (m, 3H), 7.08–7.17 (m, 6H), 7.20–7.24 (m, 3H) p.p.m.; ¹³C NMR (CDCl₃, 75 MHz) δ 60.7, 114.5, 126.2, 126.8, 127.1, 127.8, 128.0, 130.2, 131.1, 133.8, 134.5, 136.3, 141.3, 145.3, 148.4 p.p.m.

6-Methoxy-5,6-diphenyl-2,4-cyclohexadienone (IV) (Band 3): This was recrystallized from CH₂Cl₂-hexane mixture. Yield = 15 mg, 5%; mp 467–469 K (Literature mp 469–471 K (Matoba et al.,1985). ¹H NMR (CDCl₃, 300 MHz): δ 3.66 (s, 3H, OCH₃), 5.56 (d, J = 7.8 Hz, 1H), 5.88 (d, J = 9.9 Hz, 1H), 7.15–7.29 (m, 11H) p.p.m.; ¹³C NMR (CDCl₃, 75 MHz) δ 56.2, 69.5, 94.5, 118.8, 127.6, 128.3, 129.9, 141.0, 143.5, 171.2, 201.2 p.p.m.

Computing details top

Data collection: GIS (Bruker, 2009); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: local programs (Guzei, 2007) and publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling and displacement ellipsoids at the 50% probability level.
	Fig. 2. The formation of the title compound.

2-Methoxy-3,4-diphenylphenol top

Crystal data top

C₁₉H₁₆O₂	F(000) = 584
M_r = 276.32	D_x = 1.225 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 999 reflections
a = 14.312 (3) Å	θ = 2.4–25.0°
b = 6.2585 (14) Å	µ = 0.08 mm⁻¹
c = 17.167 (4) Å	T = 300 K
β = 102.930 (7)°	Block, colourless
V = 1498.7 (6) Å³	0.36 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker SMART X2S diffractometer	2645 independent reflections
Radiation source: micro-focus sealed tube	1897 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	R_int = 0.040
ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −17→17
T_min = 0.972, T_max = 0.978	k = −7→7
13658 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0877P)²] where P = (F_o² + 2F_c²)/3
2645 reflections	(Δ/σ)_max < 0.001
192 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₆O₂	V = 1498.7 (6) Å³
M_r = 276.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.312 (3) Å	µ = 0.08 mm⁻¹
b = 6.2585 (14) Å	T = 300 K
c = 17.167 (4) Å	0.36 × 0.30 × 0.28 mm
β = 102.930 (7)°

Data collection top

Bruker SMART X2S diffractometer	2645 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1897 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.978	R_int = 0.040
13658 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
2645 reflections	Δρ_min = −0.19 e Å⁻³
192 parameters

Special details top

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.

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 > σ(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	0.40221 (7)	0.44465 (18)	0.45356 (6)	0.0466 (3)
O2	0.55156 (8)	0.1831 (2)	0.44401 (8)	0.0630 (4)
H2	0.5431	0.2608	0.4803	0.095*
C1	0.39866 (10)	0.3357 (2)	0.38259 (9)	0.0388 (4)
C2	0.47494 (10)	0.2000 (3)	0.38019 (10)	0.0443 (4)
C3	0.47283 (12)	0.0780 (3)	0.31276 (11)	0.0501 (5)
H3	0.5228	−0.0155	0.3110	0.060*
C4	0.39596 (11)	0.0956 (3)	0.24786 (10)	0.0453 (4)
H4	0.3945	0.0107	0.2031	0.054*
C5	0.32054 (10)	0.2373 (2)	0.24768 (9)	0.0388 (4)
C6	0.32128 (10)	0.3600 (2)	0.31656 (9)	0.0352 (4)
C7	0.35107 (16)	0.3378 (4)	0.50515 (13)	0.0751 (6)
H7A	0.2843	0.3301	0.4795	0.113*
H7C	0.3586	0.4158	0.5543	0.113*
H7B	0.3761	0.1960	0.5162	0.113*
C8	0.24411 (10)	0.2612 (3)	0.17289 (10)	0.0413 (4)
C9	0.22906 (13)	0.4551 (3)	0.13291 (11)	0.0532 (5)
H9	0.2650	0.5736	0.1542	0.064*
C10	0.16117 (15)	0.4750 (4)	0.06154 (12)	0.0648 (6)
H10	0.1522	0.6063	0.0355	0.078*
C11	0.10739 (14)	0.3023 (4)	0.02930 (12)	0.0668 (6)
H11	0.0620	0.3157	−0.0185	0.080*
C12	0.12096 (13)	0.1098 (4)	0.06801 (13)	0.0660 (6)
H12	0.0843	−0.0074	0.0463	0.079*
C13	0.18878 (12)	0.0874 (3)	0.13916 (11)	0.0532 (5)
H13	0.1974	−0.0447	0.1646	0.064*
C14	0.24119 (10)	0.5068 (2)	0.32365 (9)	0.0368 (4)
C15	0.25989 (12)	0.7172 (3)	0.34987 (10)	0.0464 (4)
H15	0.3223	0.7691	0.3600	0.056*
C16	0.18630 (14)	0.8488 (3)	0.36086 (11)	0.0580 (5)
H16	0.1996	0.9883	0.3785	0.070*
C17	0.09338 (14)	0.7743 (3)	0.34579 (12)	0.0634 (5)
H17	0.0441	0.8626	0.3538	0.076*
C18	0.07375 (12)	0.5682 (3)	0.31880 (12)	0.0577 (5)
H18	0.0110	0.5179	0.3081	0.069*
C19	0.14693 (11)	0.4360 (3)	0.30755 (10)	0.0456 (4)
H19	0.1328	0.2975	0.2889	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0403 (6)	0.0606 (8)	0.0379 (6)	−0.0037 (5)	0.0068 (5)	−0.0070 (5)
O2	0.0436 (7)	0.0751 (10)	0.0632 (9)	0.0138 (6)	−0.0030 (6)	−0.0042 (7)
C1	0.0354 (8)	0.0435 (9)	0.0389 (9)	−0.0043 (6)	0.0114 (7)	−0.0017 (7)
C2	0.0323 (8)	0.0502 (10)	0.0499 (10)	0.0019 (7)	0.0081 (7)	0.0050 (8)
C3	0.0415 (9)	0.0498 (11)	0.0617 (12)	0.0109 (7)	0.0172 (8)	0.0012 (8)
C4	0.0473 (9)	0.0456 (10)	0.0466 (10)	0.0035 (7)	0.0184 (8)	−0.0033 (8)
C5	0.0401 (8)	0.0402 (9)	0.0387 (9)	−0.0003 (6)	0.0141 (7)	0.0010 (7)
C6	0.0315 (7)	0.0378 (8)	0.0377 (9)	−0.0010 (6)	0.0106 (6)	0.0030 (7)
C7	0.0934 (15)	0.0886 (16)	0.0522 (12)	−0.0144 (12)	0.0352 (11)	−0.0028 (11)
C8	0.0425 (8)	0.0460 (10)	0.0377 (9)	0.0045 (7)	0.0138 (7)	−0.0020 (7)
C9	0.0626 (11)	0.0505 (11)	0.0455 (10)	0.0042 (8)	0.0099 (8)	0.0000 (8)
C10	0.0763 (14)	0.0673 (13)	0.0487 (12)	0.0224 (11)	0.0096 (10)	0.0073 (10)
C11	0.0560 (11)	0.0907 (16)	0.0481 (12)	0.0149 (11)	−0.0003 (9)	−0.0069 (11)
C12	0.0487 (10)	0.0768 (15)	0.0670 (14)	−0.0026 (9)	0.0013 (9)	−0.0157 (11)
C13	0.0493 (10)	0.0531 (11)	0.0555 (11)	−0.0016 (8)	0.0082 (8)	−0.0036 (9)
C14	0.0367 (8)	0.0420 (9)	0.0320 (8)	0.0018 (6)	0.0081 (6)	−0.0003 (7)
C15	0.0510 (9)	0.0437 (10)	0.0446 (10)	−0.0018 (7)	0.0111 (7)	0.0000 (8)
C16	0.0765 (13)	0.0435 (11)	0.0527 (11)	0.0110 (9)	0.0116 (10)	−0.0052 (9)
C17	0.0588 (11)	0.0742 (14)	0.0566 (12)	0.0296 (10)	0.0112 (9)	−0.0059 (10)
C18	0.0369 (9)	0.0767 (14)	0.0582 (12)	0.0099 (8)	0.0075 (8)	−0.0063 (10)
C19	0.0365 (8)	0.0506 (10)	0.0489 (10)	0.0018 (7)	0.0075 (7)	−0.0051 (8)

Geometric parameters (Å, º) top

O1—C1	1.3871 (18)	C9—H9	0.9300
O1—C7	1.434 (2)	C10—C11	1.370 (3)
O2—C2	1.3698 (19)	C10—H10	0.9300
O2—H2	0.8200	C11—C12	1.368 (3)
C1—C2	1.391 (2)	C11—H11	0.9300
C1—C6	1.405 (2)	C12—C13	1.387 (3)
C2—C3	1.382 (2)	C12—H12	0.9300
C3—C4	1.384 (2)	C13—H13	0.9300
C3—H3	0.9300	C14—C19	1.388 (2)
C4—C5	1.397 (2)	C14—C15	1.398 (2)
C4—H4	0.9300	C15—C16	1.383 (2)
C5—C6	1.408 (2)	C15—H15	0.9300
C5—C8	1.496 (2)	C16—C17	1.378 (3)
C6—C14	1.495 (2)	C16—H16	0.9300
C7—H7A	0.9600	C17—C18	1.378 (3)
C7—H7C	0.9600	C17—H17	0.9300
C7—H7B	0.9600	C18—C19	1.382 (2)
C8—C9	1.387 (2)	C18—H18	0.9300
C8—C13	1.393 (2)	C19—H19	0.9300
C9—C10	1.389 (3)

C1—O1—C7	112.95 (13)	C10—C9—H9	119.5
C2—O2—H2	109.5	C11—C10—C9	120.29 (19)
O1—C1—C2	116.83 (13)	C11—C10—H10	119.9
O1—C1—C6	121.54 (13)	C9—C10—H10	119.9
C2—C1—C6	121.63 (14)	C12—C11—C10	119.52 (18)
O2—C2—C3	119.41 (14)	C12—C11—H11	120.2
O2—C2—C1	121.10 (15)	C10—C11—H11	120.2
C3—C2—C1	119.49 (15)	C11—C12—C13	120.80 (19)
C2—C3—C4	119.66 (15)	C11—C12—H12	119.6
C2—C3—H3	120.2	C13—C12—H12	119.6
C4—C3—H3	120.2	C12—C13—C8	120.53 (17)
C3—C4—C5	121.82 (16)	C12—C13—H13	119.7
C3—C4—H4	119.1	C8—C13—H13	119.7
C5—C4—H4	119.1	C19—C14—C15	118.20 (14)
C4—C5—C6	118.94 (14)	C19—C14—C6	121.10 (14)
C4—C5—C8	118.79 (14)	C15—C14—C6	120.66 (13)
C6—C5—C8	122.20 (13)	C16—C15—C14	120.53 (16)
C1—C6—C5	118.38 (13)	C16—C15—H15	119.7
C1—C6—C14	118.76 (13)	C14—C15—H15	119.7
C5—C6—C14	122.79 (13)	C17—C16—C15	120.36 (17)
O1—C7—H7A	109.5	C17—C16—H16	119.8
O1—C7—H7C	109.5	C15—C16—H16	119.8
H7A—C7—H7C	109.5	C18—C17—C16	119.70 (16)
O1—C7—H7B	109.5	C18—C17—H17	120.2
H7A—C7—H7B	109.5	C16—C17—H17	120.2
H7C—C7—H7B	109.5	C17—C18—C19	120.23 (17)
C9—C8—C13	117.81 (16)	C17—C18—H18	119.9
C9—C8—C5	120.99 (15)	C19—C18—H18	119.9
C13—C8—C5	121.14 (15)	C18—C19—C14	120.97 (16)
C8—C9—C10	121.06 (18)	C18—C19—H19	119.5
C8—C9—H9	119.5	C14—C19—H19	119.5

C7—O1—C1—C2	−94.89 (18)	C6—C5—C8—C13	−123.15 (17)
C7—O1—C1—C6	84.55 (18)	C13—C8—C9—C10	−0.1 (3)
O1—C1—C2—O2	−2.8 (2)	C5—C8—C9—C10	177.00 (16)
C6—C1—C2—O2	177.77 (14)	C8—C9—C10—C11	0.1 (3)
O1—C1—C2—C3	176.31 (14)	C9—C10—C11—C12	0.1 (3)
C6—C1—C2—C3	−3.1 (2)	C10—C11—C12—C13	−0.3 (3)
O2—C2—C3—C4	−179.50 (15)	C11—C12—C13—C8	0.4 (3)
C1—C2—C3—C4	1.4 (2)	C9—C8—C13—C12	−0.2 (2)
C2—C3—C4—C5	1.3 (3)	C5—C8—C13—C12	−177.25 (16)
C3—C4—C5—C6	−2.3 (2)	C1—C6—C14—C19	−125.28 (16)
C3—C4—C5—C8	174.84 (15)	C5—C6—C14—C19	51.8 (2)
O1—C1—C6—C5	−177.28 (13)	C1—C6—C14—C15	52.1 (2)
C2—C1—C6—C5	2.1 (2)	C5—C6—C14—C15	−130.82 (16)
O1—C1—C6—C14	−0.1 (2)	C19—C14—C15—C16	1.3 (2)
C2—C1—C6—C14	179.32 (14)	C6—C14—C15—C16	−176.18 (15)
C4—C5—C6—C1	0.6 (2)	C14—C15—C16—C17	−0.2 (3)
C8—C5—C6—C1	−176.46 (13)	C15—C16—C17—C18	−0.7 (3)
C4—C5—C6—C14	−176.52 (13)	C16—C17—C18—C19	0.6 (3)
C8—C5—C6—C14	6.5 (2)	C17—C18—C19—C14	0.5 (3)
C4—C5—C8—C9	−117.18 (18)	C15—C14—C19—C18	−1.4 (2)
C6—C5—C8—C9	59.8 (2)	C6—C14—C19—C18	176.05 (15)
C4—C5—C8—C13	59.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.21	2.9043 (18)	142

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₂
M_r	276.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	14.312 (3), 6.2585 (14), 17.167 (4)
β (°)	102.930 (7)
V (Å³)	1498.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART X2S diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.972, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	13658, 2645, 1897
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.129, 1.01
No. of reflections	2645
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: GIS (Bruker, 2009), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009), local programs (Guzei, 2007) and publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.21	2.9043 (18)	142

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

We gratefully acknowledge Bruker sponsorship of this publication. Support of the photochemical research by the NSF is gratefully acknowledged.

References

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