1-(4-Bromo­phenyl­sulfin­yl)-2-methyl­naphtho­[2,1-b]furan

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812012603

organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Page o1246

doi:10.1107/S1600536812012603

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1-(4-Bromophenylsulfinyl)-2-methylnaphtho[2,1-b]furan

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 21 March 2012; accepted 23 March 2012; online 31 March 2012)

In the title compound, C₁₉H₁₃BrO₂S, the 4-bromophenyl ring makes a dihedral angle of 83.75 (4)° with the mean plane of the naphthofuran fragment [r.m.s. deviation = 0.024 (2) Å]. In the crystal, molecules are linked via pairs of C—H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak π–π interactions between the central naphthofuran benzene rings of neighbouring molecules [centroid–centroid distance = 3.483 (2) Å, interplanar distance = 3.416 (2) Å and slippage = 0.680 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2007 , 2012 ).

Experimental

Crystal data

C₁₉H₁₃BrO₂S
M_r = 385.26
Triclinic, $[P \overline 1]$
a = 8.7124 (1) Å
b = 9.4857 (1) Å
c = 10.2898 (1) Å
α = 82.883 (1)°
β = 71.126 (1)°
γ = 75.672 (1)°
V = 778.74 (2) Å³
Z = 2
Mo Kα radiation
μ = 2.78 mm⁻¹
T = 173 K
0.33 × 0.29 × 0.27 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.462, T_max = 0.517
14577 measured reflections
3853 independent reflections
3461 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.080
S = 1.05
3853 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.60 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O2ⁱ	0.95	2.35	3.221 (2)	152
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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 DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812012603/sj5222sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012603/sj5222Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812012603/sj5222Isup3.cml

checkCIF report

Comment top

As a part of our ongoing study of 2-methylnaphtho[2,1-b]furan derivatives containing 1-phenylsulfinyl (Choi et al., 2007) and 1-(4-methylphenylsulfinyl) (Choi et al., 2012) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the naphthofuran unit is essentially planar, with a mean deviation of 0.024 (2) Å from the least-squares plane defined by the thirteen constituent atoms. The dihedral angle between the 4-bromophenyl ring and the mean plane of the naphthofuran fragment is 83.75 (4)°. In the crystal structure, molecules are linked via pairs of C—H···O hydrogen bonds (Fig. 2 & Table 1), forming inversion dimers. These dimers are connected by weak π–π interactions between the central naphthofuran benzene rings of neighbouring molecules, with a Cg···Cgⁱⁱ distance of 3.483 (2) Å and an interplanar distance of 3.416 (2) Å resulting in a slippage of 0.680 (2) Å (Fig. 2, Cg is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2007, 2012).

Experimental top

77% 3-Chloroperoxybenzoic acid (202 mg, 0.9 mmol) was added in small portions to a stirred solution of 1-(4-bromophenylsulfanyl)-2-methylnaphtho [2,1-b]furan (295 mg, 0.8 mmol) in dichloromethane (40 mL) at 273 K. After being stirred at room temperature for 5h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 466–467 K; R_f = 0.59 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in acetone at room temperature.

Structure description top

For background information and the crystal structures of related compounds, see: Choi et al. (2007, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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 DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
	Fig. 2. A view of the C—H···O and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) - x + 1, - y + 1, - z ; (ii) - x + 1 , - y + 1, - z + 1.]

1-(4-Bromophenylsulfinyl)-2-methylnaphtho[2,1-b]furan top

Crystal data top

C₁₉H₁₃BrO₂S	Z = 2
M_r = 385.26	F(000) = 388
Triclinic, P1	D_x = 1.643 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7124 (1) Å	Cell parameters from 7454 reflections
b = 9.4857 (1) Å	θ = 2.5–28.3°
c = 10.2898 (1) Å	µ = 2.78 mm⁻¹
α = 82.883 (1)°	T = 173 K
β = 71.126 (1)°	Block, colourless
γ = 75.672 (1)°	0.33 × 0.29 × 0.27 mm
V = 778.74 (2) Å³

Data collection top

Bruker SMART APEXII CCD diffractometer	3853 independent reflections
Radiation source: rotating anode	3461 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.031
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
T_min = 0.462, T_max = 0.517	l = −13→13
14577 measured reflections

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)] = 0.030	Hydrogen site location: difference Fourier map
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0424P)² + 0.3115P] where P = (F_o² + 2F_c²)/3
3853 reflections	(Δ/σ)_max = 0.002
209 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.60 e Å⁻³

Crystal data top

C₁₉H₁₃BrO₂S	γ = 75.672 (1)°
M_r = 385.26	V = 778.74 (2) Å³
Triclinic, P1	Z = 2
a = 8.7124 (1) Å	Mo Kα radiation
b = 9.4857 (1) Å	µ = 2.78 mm⁻¹
c = 10.2898 (1) Å	T = 173 K
α = 82.883 (1)°	0.33 × 0.29 × 0.27 mm
β = 71.126 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3853 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3461 reflections with I > 2σ(I)
T_min = 0.462, T_max = 0.517	R_int = 0.031
14577 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.05	Δρ_max = 0.62 e Å⁻³
3853 reflections	Δρ_min = −0.60 e Å⁻³
209 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
Br1	1.00152 (2)	−0.12635 (2)	−0.16983 (2)	0.03951 (8)
S1	0.35059 (5)	0.29100 (5)	0.20858 (4)	0.02531 (10)
O1	0.39380 (18)	0.19036 (15)	0.57662 (13)	0.0339 (3)
O2	0.34216 (16)	0.44277 (15)	0.14815 (14)	0.0308 (3)
C1	0.4076 (2)	0.27335 (19)	0.36023 (17)	0.0248 (3)
C2	0.5387 (2)	0.31553 (19)	0.39413 (17)	0.0241 (3)
C3	0.6643 (2)	0.39490 (19)	0.32814 (17)	0.0236 (3)
C4	0.6876 (2)	0.46220 (19)	0.19438 (17)	0.0243 (3)
H4	0.6154	0.4567	0.1439	0.029*
C5	0.8127 (2)	0.5349 (2)	0.1373 (2)	0.0295 (4)
H5	0.8265	0.5795	0.0475	0.035*
C6	0.9214 (2)	0.5446 (2)	0.2102 (2)	0.0357 (4)
H6	1.0098	0.5933	0.1689	0.043*
C7	0.8993 (3)	0.4836 (2)	0.3402 (2)	0.0357 (4)
H7	0.9721	0.4918	0.3892	0.043*
C8	0.7706 (2)	0.4086 (2)	0.40403 (19)	0.0295 (4)
C9	0.7452 (3)	0.3495 (2)	0.5420 (2)	0.0357 (4)
H9	0.8165	0.3611	0.5910	0.043*
C10	0.6220 (3)	0.2772 (2)	0.60542 (19)	0.0353 (4)
H10	0.6045	0.2392	0.6976	0.042*
C11	0.5225 (2)	0.2618 (2)	0.52789 (18)	0.0293 (4)
C12	0.3248 (2)	0.2003 (2)	0.47280 (19)	0.0301 (4)
C13	0.1834 (3)	0.1278 (3)	0.5032 (2)	0.0419 (5)
H13A	0.1309	0.1541	0.4299	0.063*
H13B	0.1017	0.1594	0.5912	0.063*
H13C	0.2243	0.0219	0.5087	0.063*
C14	0.5374 (2)	0.17880 (19)	0.10434 (17)	0.0234 (3)
C15	0.5817 (3)	0.0335 (2)	0.14588 (19)	0.0313 (4)
H15	0.5173	−0.0031	0.2308	0.038*
C16	0.7191 (3)	−0.0578 (2)	0.0640 (2)	0.0333 (4)
H16	0.7497	−0.1574	0.0916	0.040*
C17	0.8116 (2)	−0.0017 (2)	−0.05890 (19)	0.0283 (4)
C18	0.7683 (2)	0.1426 (2)	−0.10104 (18)	0.0286 (4)
H18	0.8335	0.1792	−0.1855	0.034*
C19	0.6289 (2)	0.2341 (2)	−0.01936 (17)	0.0259 (3)
H19	0.5970	0.3332	−0.0480	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03626 (13)	0.03675 (14)	0.04460 (13)	−0.00190 (9)	−0.01114 (9)	−0.01442 (9)
S1	0.0229 (2)	0.0272 (2)	0.0268 (2)	−0.00701 (17)	−0.01025 (16)	0.00538 (16)
O1	0.0371 (7)	0.0337 (8)	0.0231 (6)	−0.0025 (6)	−0.0056 (5)	0.0069 (5)
O2	0.0278 (6)	0.0283 (7)	0.0344 (7)	−0.0035 (5)	−0.0129 (5)	0.0092 (5)
C1	0.0234 (8)	0.0242 (9)	0.0231 (8)	−0.0015 (7)	−0.0060 (6)	0.0016 (6)
C2	0.0258 (8)	0.0217 (8)	0.0212 (7)	0.0024 (6)	−0.0078 (6)	−0.0021 (6)
C3	0.0239 (8)	0.0210 (8)	0.0239 (8)	0.0013 (6)	−0.0079 (6)	−0.0047 (6)
C4	0.0247 (8)	0.0214 (8)	0.0261 (8)	−0.0015 (7)	−0.0089 (6)	−0.0025 (6)
C5	0.0287 (9)	0.0254 (9)	0.0324 (9)	−0.0046 (7)	−0.0069 (7)	−0.0034 (7)
C6	0.0304 (9)	0.0314 (11)	0.0481 (11)	−0.0095 (8)	−0.0112 (8)	−0.0084 (8)
C7	0.0330 (10)	0.0342 (11)	0.0458 (11)	−0.0035 (8)	−0.0194 (9)	−0.0117 (8)
C8	0.0307 (9)	0.0272 (10)	0.0318 (9)	0.0023 (7)	−0.0147 (7)	−0.0092 (7)
C9	0.0418 (11)	0.0343 (11)	0.0346 (10)	0.0050 (8)	−0.0240 (9)	−0.0080 (8)
C10	0.0452 (11)	0.0334 (11)	0.0232 (8)	0.0054 (9)	−0.0152 (8)	−0.0022 (7)
C11	0.0313 (9)	0.0271 (9)	0.0240 (8)	0.0020 (7)	−0.0077 (7)	−0.0001 (7)
C12	0.0284 (9)	0.0273 (10)	0.0272 (8)	−0.0004 (7)	−0.0040 (7)	0.0026 (7)
C13	0.0353 (11)	0.0409 (12)	0.0419 (11)	−0.0124 (9)	−0.0024 (9)	0.0092 (9)
C14	0.0276 (8)	0.0228 (9)	0.0229 (8)	−0.0076 (7)	−0.0114 (6)	0.0020 (6)
C15	0.0411 (10)	0.0259 (10)	0.0266 (8)	−0.0120 (8)	−0.0092 (8)	0.0058 (7)
C16	0.0460 (11)	0.0202 (9)	0.0339 (9)	−0.0064 (8)	−0.0143 (8)	0.0017 (7)
C17	0.0314 (9)	0.0274 (9)	0.0300 (9)	−0.0063 (7)	−0.0132 (7)	−0.0061 (7)
C18	0.0326 (9)	0.0314 (10)	0.0236 (8)	−0.0103 (8)	−0.0096 (7)	0.0018 (7)
C19	0.0325 (9)	0.0229 (9)	0.0245 (8)	−0.0073 (7)	−0.0130 (7)	0.0044 (6)

Geometric parameters (Å, º) top

Br1—C17	1.8932 (19)	C8—C9	1.428 (3)
S1—O2	1.4899 (13)	C9—C10	1.360 (3)
S1—C1	1.7621 (17)	C9—H9	0.9500
S1—C14	1.7966 (19)	C10—C11	1.395 (3)
O1—C12	1.369 (2)	C10—H10	0.9500
O1—C11	1.378 (2)	C12—C13	1.486 (3)
C1—C12	1.360 (2)	C13—H13A	0.9800
C1—C2	1.451 (2)	C13—H13B	0.9800
C2—C11	1.382 (2)	C13—H13C	0.9800
C2—C3	1.424 (2)	C14—C19	1.384 (2)
C3—C4	1.417 (2)	C14—C15	1.389 (3)
C3—C8	1.427 (2)	C15—C16	1.381 (3)
C4—C5	1.366 (2)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.385 (3)
C5—C6	1.411 (3)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.380 (3)
C6—C7	1.363 (3)	C18—C19	1.390 (3)
C6—H6	0.9500	C18—H18	0.9500
C7—C8	1.413 (3)	C19—H19	0.9500
C7—H7	0.9500

O2—S1—C1	110.36 (8)	C9—C10—H10	121.8
O2—S1—C14	107.32 (8)	C11—C10—H10	121.8
C1—S1—C14	97.62 (8)	O1—C11—C2	111.20 (16)
C12—O1—C11	106.47 (13)	O1—C11—C10	123.59 (16)
C12—C1—C2	107.38 (15)	C2—C11—C10	125.21 (18)
C12—C1—S1	119.35 (14)	C1—C12—O1	110.59 (16)
C2—C1—S1	133.18 (13)	C1—C12—C13	133.92 (18)
C11—C2—C3	118.75 (16)	O1—C12—C13	115.46 (16)
C11—C2—C1	104.35 (15)	C12—C13—H13A	109.5
C3—C2—C1	136.87 (15)	C12—C13—H13B	109.5
C4—C3—C2	124.19 (15)	H13A—C13—H13B	109.5
C4—C3—C8	118.74 (16)	C12—C13—H13C	109.5
C2—C3—C8	117.06 (15)	H13A—C13—H13C	109.5
C5—C4—C3	120.72 (16)	H13B—C13—H13C	109.5
C5—C4—H4	119.6	C19—C14—C15	120.80 (17)
C3—C4—H4	119.6	C19—C14—S1	120.37 (14)
C4—C5—C6	120.68 (17)	C15—C14—S1	118.69 (13)
C4—C5—H5	119.7	C16—C15—C14	120.14 (17)
C6—C5—H5	119.7	C16—C15—H15	119.9
C7—C6—C5	119.72 (18)	C14—C15—H15	119.9
C7—C6—H6	120.1	C15—C16—C17	118.89 (18)
C5—C6—H6	120.1	C15—C16—H16	120.6
C6—C7—C8	121.57 (17)	C17—C16—H16	120.6
C6—C7—H7	119.2	C18—C17—C16	121.34 (18)
C8—C7—H7	119.2	C18—C17—Br1	119.83 (14)
C7—C8—C3	118.50 (17)	C16—C17—Br1	118.84 (15)
C7—C8—C9	121.04 (17)	C17—C18—C19	119.77 (16)
C3—C8—C9	120.45 (18)	C17—C18—H18	120.1
C10—C9—C8	122.03 (18)	C19—C18—H18	120.1
C10—C9—H9	119.0	C14—C19—C18	119.05 (16)
C8—C9—H9	119.0	C14—C19—H19	120.5
C9—C10—C11	116.45 (17)	C18—C19—H19	120.5

O2—S1—C1—C12	135.73 (15)	C12—O1—C11—C10	178.95 (18)
C14—S1—C1—C12	−112.55 (16)	C3—C2—C11—O1	178.96 (15)
O2—S1—C1—C2	−48.3 (2)	C1—C2—C11—O1	0.4 (2)
C14—S1—C1—C2	63.40 (19)	C3—C2—C11—C10	−0.8 (3)
C12—C1—C2—C11	0.2 (2)	C1—C2—C11—C10	−179.41 (18)
S1—C1—C2—C11	−176.07 (15)	C9—C10—C11—O1	179.36 (18)
C12—C1—C2—C3	−177.9 (2)	C9—C10—C11—C2	−0.9 (3)
S1—C1—C2—C3	5.8 (3)	C2—C1—C12—O1	−0.8 (2)
C11—C2—C3—C4	−176.38 (17)	S1—C1—C12—O1	176.13 (13)
C1—C2—C3—C4	1.6 (3)	C2—C1—C12—C13	−178.5 (2)
C11—C2—C3—C8	2.4 (3)	S1—C1—C12—C13	−1.6 (3)
C1—C2—C3—C8	−179.6 (2)	C11—O1—C12—C1	1.0 (2)
C2—C3—C4—C5	−179.11 (17)	C11—O1—C12—C13	179.19 (18)
C8—C3—C4—C5	2.1 (3)	O2—S1—C14—C19	−9.52 (16)
C3—C4—C5—C6	0.0 (3)	C1—S1—C14—C19	−123.69 (14)
C4—C5—C6—C7	−1.5 (3)	O2—S1—C14—C15	174.66 (14)
C5—C6—C7—C8	0.9 (3)	C1—S1—C14—C15	60.49 (15)
C6—C7—C8—C3	1.2 (3)	C19—C14—C15—C16	0.4 (3)
C6—C7—C8—C9	−177.87 (19)	S1—C14—C15—C16	176.20 (15)
C4—C3—C8—C7	−2.7 (3)	C14—C15—C16—C17	0.4 (3)
C2—C3—C8—C7	178.44 (17)	C15—C16—C17—C18	−0.5 (3)
C4—C3—C8—C9	176.43 (17)	C15—C16—C17—Br1	179.21 (14)
C2—C3—C8—C9	−2.5 (3)	C16—C17—C18—C19	−0.2 (3)
C7—C8—C9—C10	179.9 (2)	Br1—C17—C18—C19	−179.89 (13)
C3—C8—C9—C10	0.8 (3)	C15—C14—C19—C18	−1.1 (3)
C8—C9—C10—C11	0.9 (3)	S1—C14—C19—C18	−176.81 (13)
C12—O1—C11—C2	−0.9 (2)	C17—C18—C19—C14	1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱ	0.95	2.35	3.221 (2)	152

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrO₂S
M_r	385.26
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	8.7124 (1), 9.4857 (1), 10.2898 (1)
α, β, γ (°)	82.883 (1), 71.126 (1), 75.672 (1)
V (Å³)	778.74 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.78
Crystal size (mm)	0.33 × 0.29 × 0.27

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.462, 0.517
No. of measured, independent and observed [I > 2σ(I)] reflections	14577, 3853, 3461
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.05
No. of reflections	3853
No. of parameters	209
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.60

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O2ⁱ	0.95	2.35	3.221 (2)	152.2

Symmetry code: (i) −x+1, −y+1, −z.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o549. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o1731–o1732. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Page o1246

doi:10.1107/S1600536812012603

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