3-(4-Fluoro­phenyl­sulfon­yl)-5-iodo-2,7-dimethyl-1-benzofuran

Seo, P.J.; Choi, H.D.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811052792

organic compounds

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ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page o96

doi:10.1107/S1600536811052792

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3-(4-Fluorophenylsulfonyl)-5-iodo-2,7-dimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^a Byeng Wha Son ^b 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 6 December 2011; accepted 7 December 2011; online 10 December 2011)

In the title compound, C₁₆H₁₂FIO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, and by an I⋯I contact [3.7764 (3) Å]. The crystal structure also exhibits a weak C—I⋯π [3.901 (3) Å] interaction and a slipped π–π interaction between the furan and benzene rings of neighbouring molecules [centroid–centroid distance = 3.845 (3), interplanar distance = 3.555 (3) and slippage = 1.465 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009 ); Galal et al. (2009 ); Khan et al. (2005 ). For natural products with benzofuran rings, see: Akgul & Anil (2003 ); Soekamto et al. (2003 ). For related structures, see: Choi et al. (2008 , 2011 ).

Experimental

Crystal data

C₁₆H₁₂FIO₃S
M_r = 430.22
Triclinic, $[P \overline 1]$
a = 7.5839 (2) Å
b = 10.2443 (3) Å
c = 10.4651 (3) Å
α = 79.424 (1)°
β = 75.652 (1)°
γ = 80.361 (1)°
V = 767.94 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.24 mm⁻¹
T = 173 K
0.32 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.534, T_max = 0.689
13962 measured reflections
3785 independent reflections
3585 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.057
S = 1.08
3785 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O3ⁱ	0.95	2.54	3.253 (2)	132
C15—H15⋯O2ⁱⁱ	0.95	2.52	3.294 (3)	139
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+1.

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/S1600536811052792/bh2405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811052792/bh2405Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811052792/bh2405Isup3.cml

checkCIF report

Comment top

Recently, benzofuran derivatives have drawn much attention due to their valuable pharmacological properties such as antibacterial and antifungal, antitumor and antiviral, and antimicrobial activities (Aslam et al., 2009; Galal et al., 2009; Khan et al., 2005). These benzofuran derivatives occur in a wide range of natural products (Akgul & Anil, 2003; Soekamto et al., 2003). As a part of our ongoing study of benzofuran derivatives containing either 3-phenylsulfonyl (Choi et al., 2008) or 3-(4-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.007 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane of the benzofurn fragment is 72.31 (6)°. The crystal packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds (see Table 1), and by an I···I contact at 3.7764 (3) Å. The crystal packing (Fig. 3) is further stabilized by a weak C—I···π interaction between the iodine and the benzene ring of an adjacent molecule, with a C4—I1···Cg2^v [3.901 (3) Å] (Cg2 is the centroid of the C2···C7 benzene ring). The crystal packing (Fig. 3) is also exhibits a weak slipped π–π interaction between the furan and benzene rings of adjacent molecules, with a Cg1···Cg2^iv distance of 3.845 (3) Å and an interplanar distance of 3.555 (3) Å resulting in a slippage of 1.465 (3) Å (Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring).

Related literature top

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2008, 2011).

Experimental top

77% 3-chloroperoxybenzoic acid (381 mg, 1.7 mmol) was added in small portions to a stirred solution of 3-(4-fluorophenylsulfanyl)-5-iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 8 h, 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, 4:1 v/v) to afford the title compound as a colorless solid [yield 71%, m.p. 430–431 K; R_f = 0.53 (hexane–ethyl acetate, 4:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

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 displacement ellipsoids 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 I···I 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, -y, -z+2; (iii) -x+1, -y, -z+1].
	Fig. 3. A view of the C—I···π and π–π interactions (dotted lines) in the crystal structure of the title compound. H atoms were omitted for clarity [Symmetry codes: (iv) -x, -y+1, -z+1; (v) -x+1, -y+1, -z+1].

3-(4-Fluorophenylsulfonyl)-5-iodo-2,7-dimethyl-1-benzofuran top

Crystal data top

C₁₆H₁₂FIO₃S	Z = 2
M_r = 430.22	F(000) = 420
Triclinic, P1	D_x = 1.861 Mg m⁻³
Hall symbol: -P 1	Melting point: 430 K
a = 7.5839 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2443 (3) Å	Cell parameters from 9929 reflections
c = 10.4651 (3) Å	θ = 2.7–28.3°
α = 79.424 (1)°	µ = 2.24 mm⁻¹
β = 75.652 (1)°	T = 173 K
γ = 80.361 (1)°	Block, colourless
V = 767.94 (4) Å³	0.32 × 0.30 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	3785 independent reflections
Radiation source: rotating anode	3585 reflections with I > 2σ(I)
Graphite multilayer monochromator	R_int = 0.028
Detector resolution: 10.0 pixels mm^-1	θ_max = 28.3°, θ_min = 2.0°
ϕ and ω scans	h = −9→10
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −13→13
T_min = 0.534, T_max = 0.689	l = −13→13
13962 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)] = 0.022	Hydrogen site location: difference Fourier map
wR(F²) = 0.057	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.028P)² + 0.3904P] where P = (F_o² + 2F_c²)/3
3785 reflections	(Δ/σ)_max = 0.001
201 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³
0 constraints

Crystal data top

C₁₆H₁₂FIO₃S	γ = 80.361 (1)°
M_r = 430.22	V = 767.94 (4) Å³
Triclinic, P1	Z = 2
a = 7.5839 (2) Å	Mo Kα radiation
b = 10.2443 (3) Å	µ = 2.24 mm⁻¹
c = 10.4651 (3) Å	T = 173 K
α = 79.424 (1)°	0.32 × 0.30 × 0.18 mm
β = 75.652 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3785 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3585 reflections with I > 2σ(I)
T_min = 0.534, T_max = 0.689	R_int = 0.028
13962 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.08	Δρ_max = 0.47 e Å⁻³
3785 reflections	Δρ_min = −0.72 e Å⁻³
201 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.458085 (17)	0.514608 (14)	0.182660 (11)	0.03682 (6)
S1	0.09268 (6)	0.13784 (4)	0.70600 (4)	0.02423 (9)
F1	0.7392 (2)	−0.17671 (16)	0.86383 (18)	0.0602 (4)
O1	0.07637 (18)	0.50285 (12)	0.77645 (12)	0.0243 (2)
O2	0.1076 (2)	0.12200 (14)	0.56993 (14)	0.0337 (3)
O3	−0.06489 (19)	0.09921 (14)	0.80627 (15)	0.0332 (3)
C1	0.1071 (2)	0.30519 (17)	0.70547 (17)	0.0227 (3)
C2	0.1812 (2)	0.39985 (16)	0.59204 (17)	0.0219 (3)
C3	0.2651 (2)	0.39515 (18)	0.45767 (17)	0.0242 (3)
H3	0.2828	0.3154	0.4195	0.029*
C4	0.3210 (2)	0.51397 (19)	0.38343 (17)	0.0259 (3)
C5	0.2946 (3)	0.63304 (18)	0.43641 (19)	0.0281 (4)
H5	0.3345	0.7114	0.3802	0.034*
C6	0.2110 (3)	0.63949 (17)	0.56963 (19)	0.0261 (3)
C7	0.1583 (2)	0.51938 (17)	0.64268 (17)	0.0226 (3)
C8	0.0489 (2)	0.37130 (17)	0.81325 (18)	0.0242 (3)
C9	0.1834 (3)	0.76435 (19)	0.6319 (2)	0.0358 (4)
H9A	0.2786	0.7597	0.6817	0.054*
H9B	0.0623	0.7723	0.6928	0.054*
H9C	0.1914	0.8425	0.5620	0.054*
C10	−0.0272 (3)	0.3303 (2)	0.95636 (18)	0.0326 (4)
H10A	−0.0523	0.2373	0.9712	0.049*
H10B	−0.1414	0.3885	0.9853	0.049*
H10C	0.0616	0.3379	1.0077	0.049*
C11	0.2897 (2)	0.04748 (16)	0.75598 (17)	0.0239 (3)
C12	0.2733 (3)	−0.02336 (19)	0.88349 (19)	0.0318 (4)
H12	0.1580	−0.0191	0.9453	0.038*
C13	0.4256 (3)	−0.1004 (2)	0.9203 (2)	0.0391 (5)
H13	0.4169	−0.1514	1.0067	0.047*
C14	0.5908 (3)	−0.1011 (2)	0.8280 (2)	0.0380 (4)
C15	0.6120 (3)	−0.0298 (2)	0.7025 (2)	0.0368 (4)
H15	0.7288	−0.0318	0.6425	0.044*
C16	0.4587 (3)	0.0453 (2)	0.66519 (19)	0.0304 (4)
H16	0.4686	0.0951	0.5783	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.03090 (8)	0.05323 (10)	0.02085 (7)	−0.00336 (6)	−0.00149 (5)	0.00069 (5)
S1	0.0273 (2)	0.02141 (18)	0.0241 (2)	−0.00622 (16)	−0.00472 (16)	−0.00224 (15)
F1	0.0409 (8)	0.0588 (9)	0.0736 (11)	0.0116 (7)	−0.0215 (7)	0.0040 (8)
O1	0.0276 (6)	0.0228 (6)	0.0215 (6)	−0.0025 (5)	−0.0034 (5)	−0.0042 (4)
O2	0.0468 (8)	0.0291 (7)	0.0292 (7)	−0.0055 (6)	−0.0134 (6)	−0.0071 (5)
O3	0.0276 (7)	0.0322 (7)	0.0373 (8)	−0.0115 (5)	−0.0017 (6)	0.0002 (6)
C1	0.0243 (8)	0.0213 (7)	0.0219 (8)	−0.0038 (6)	−0.0043 (6)	−0.0018 (6)
C2	0.0204 (8)	0.0220 (7)	0.0225 (8)	−0.0020 (6)	−0.0046 (6)	−0.0024 (6)
C3	0.0237 (8)	0.0260 (8)	0.0221 (8)	−0.0020 (6)	−0.0043 (6)	−0.0032 (6)
C4	0.0227 (8)	0.0328 (9)	0.0199 (8)	−0.0028 (7)	−0.0035 (6)	−0.0002 (7)
C5	0.0273 (9)	0.0271 (8)	0.0282 (9)	−0.0061 (7)	−0.0073 (7)	0.0043 (7)
C6	0.0264 (9)	0.0223 (8)	0.0299 (9)	−0.0037 (6)	−0.0080 (7)	−0.0016 (7)
C7	0.0215 (8)	0.0235 (8)	0.0220 (8)	−0.0017 (6)	−0.0040 (6)	−0.0033 (6)
C8	0.0238 (8)	0.0247 (8)	0.0239 (8)	−0.0036 (6)	−0.0054 (6)	−0.0026 (6)
C9	0.0468 (12)	0.0237 (8)	0.0384 (11)	−0.0065 (8)	−0.0107 (9)	−0.0050 (8)
C10	0.0386 (11)	0.0356 (10)	0.0208 (8)	−0.0062 (8)	−0.0015 (7)	−0.0028 (7)
C11	0.0271 (9)	0.0191 (7)	0.0240 (8)	−0.0036 (6)	−0.0033 (6)	−0.0026 (6)
C12	0.0320 (10)	0.0310 (9)	0.0272 (9)	−0.0056 (7)	−0.0011 (7)	0.0026 (7)
C13	0.0424 (12)	0.0353 (10)	0.0342 (10)	−0.0031 (9)	−0.0099 (9)	0.0088 (8)
C14	0.0342 (11)	0.0324 (10)	0.0470 (12)	0.0029 (8)	−0.0133 (9)	−0.0057 (9)
C15	0.0282 (10)	0.0413 (11)	0.0382 (11)	−0.0025 (8)	−0.0010 (8)	−0.0100 (9)
C16	0.0308 (10)	0.0329 (9)	0.0252 (8)	−0.0066 (7)	−0.0006 (7)	−0.0037 (7)

Geometric parameters (Å, º) top

I1—C4	2.1000 (17)	C6—C9	1.501 (3)
I1—I1ⁱ	3.7764 (3)	C8—C10	1.475 (2)
S1—O2	1.4372 (14)	C9—H9A	0.9800
S1—O3	1.4388 (14)	C9—H9B	0.9800
S1—C1	1.7349 (17)	C9—H9C	0.9800
S1—C11	1.7633 (19)	C10—H10A	0.9800
F1—C14	1.348 (3)	C10—H10B	0.9800
O1—C8	1.368 (2)	C10—H10C	0.9800
O1—C7	1.375 (2)	C11—C12	1.384 (3)
C1—C8	1.364 (2)	C11—C16	1.393 (2)
C1—C2	1.447 (2)	C12—C13	1.382 (3)
C2—C7	1.390 (2)	C12—H12	0.9500
C2—C3	1.398 (2)	C13—C14	1.379 (3)
C3—C4	1.388 (2)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.367 (3)
C4—C5	1.395 (3)	C15—C16	1.382 (3)
C5—C6	1.390 (3)	C15—H15	0.9500
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.388 (2)

C4—I1—I1ⁱ	159.65 (5)	O1—C8—C10	115.71 (15)
O2—S1—O3	119.47 (9)	C6—C9—H9A	109.5
O2—S1—C1	106.66 (8)	C6—C9—H9B	109.5
O3—S1—C1	108.80 (8)	H9A—C9—H9B	109.5
O2—S1—C11	107.68 (9)	C6—C9—H9C	109.5
O3—S1—C11	107.59 (9)	H9A—C9—H9C	109.5
C1—S1—C11	105.89 (8)	H9B—C9—H9C	109.5
C8—O1—C7	107.10 (13)	C8—C10—H10A	109.5
C8—C1—C2	107.64 (15)	C8—C10—H10B	109.5
C8—C1—S1	125.62 (13)	H10A—C10—H10B	109.5
C2—C1—S1	126.74 (13)	C8—C10—H10C	109.5
C7—C2—C3	119.58 (16)	H10A—C10—H10C	109.5
C7—C2—C1	104.40 (14)	H10B—C10—H10C	109.5
C3—C2—C1	136.01 (16)	C12—C11—C16	120.97 (18)
C4—C3—C2	116.04 (16)	C12—C11—S1	119.54 (14)
C4—C3—H3	122.0	C16—C11—S1	119.47 (14)
C2—C3—H3	122.0	C13—C12—C11	119.60 (18)
C3—C4—C5	123.23 (16)	C13—C12—H12	120.2
C3—C4—I1	118.75 (13)	C11—C12—H12	120.2
C5—C4—I1	118.01 (13)	C14—C13—C12	118.06 (19)
C6—C5—C4	121.44 (16)	C14—C13—H13	121.0
C6—C5—H5	119.3	C12—C13—H13	121.0
C4—C5—H5	119.3	F1—C14—C15	118.3 (2)
C7—C6—C5	114.51 (16)	F1—C14—C13	118.0 (2)
C7—C6—C9	122.07 (17)	C15—C14—C13	123.6 (2)
C5—C6—C9	123.40 (17)	C14—C15—C16	118.16 (19)
O1—C7—C6	124.09 (15)	C14—C15—H15	120.9
O1—C7—C2	110.72 (14)	C16—C15—H15	120.9
C6—C7—C2	125.19 (16)	C15—C16—C11	119.55 (19)
C1—C8—O1	110.13 (15)	C15—C16—H16	120.2
C1—C8—C10	134.10 (16)	C11—C16—H16	120.2

O2—S1—C1—C8	160.36 (16)	C3—C2—C7—O1	−178.98 (15)
O3—S1—C1—C8	30.24 (19)	C1—C2—C7—O1	−0.15 (19)
C11—S1—C1—C8	−85.14 (18)	C3—C2—C7—C6	0.7 (3)
O2—S1—C1—C2	−19.34 (19)	C1—C2—C7—C6	179.55 (17)
O3—S1—C1—C2	−149.46 (16)	C2—C1—C8—O1	1.5 (2)
C11—S1—C1—C2	95.16 (17)	S1—C1—C8—O1	−178.27 (13)
C8—C1—C2—C7	−0.8 (2)	C2—C1—C8—C10	−175.6 (2)
S1—C1—C2—C7	178.95 (14)	S1—C1—C8—C10	4.7 (3)
C8—C1—C2—C3	177.7 (2)	C7—O1—C8—C1	−1.56 (19)
S1—C1—C2—C3	−2.5 (3)	C7—O1—C8—C10	176.10 (16)
C7—C2—C3—C4	0.2 (3)	O2—S1—C11—C12	−140.80 (15)
C1—C2—C3—C4	−178.18 (19)	O3—S1—C11—C12	−10.81 (17)
C2—C3—C4—C5	−0.9 (3)	C1—S1—C11—C12	105.39 (16)
C2—C3—C4—I1	177.53 (12)	O2—S1—C11—C16	37.34 (17)
I1ⁱ—I1—C4—C3	63.4 (2)	O3—S1—C11—C16	167.33 (14)
I1ⁱ—I1—C4—C5	−118.06 (16)	C1—S1—C11—C16	−76.46 (16)
C3—C4—C5—C6	0.8 (3)	C16—C11—C12—C13	−1.8 (3)
I1—C4—C5—C6	−177.66 (14)	S1—C11—C12—C13	176.32 (16)
C4—C5—C6—C7	0.1 (3)	C11—C12—C13—C14	1.4 (3)
C4—C5—C6—C9	178.53 (19)	C12—C13—C14—F1	−179.7 (2)
C8—O1—C7—C6	−178.67 (17)	C12—C13—C14—C15	0.1 (4)
C8—O1—C7—C2	1.04 (19)	F1—C14—C15—C16	178.6 (2)
C5—C6—C7—O1	178.82 (16)	C13—C14—C15—C16	−1.2 (3)
C9—C6—C7—O1	0.4 (3)	C14—C15—C16—C11	0.8 (3)
C5—C6—C7—C2	−0.8 (3)	C12—C11—C16—C15	0.7 (3)
C9—C6—C7—C2	−179.31 (18)	S1—C11—C16—C15	−177.42 (15)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3ⁱⁱ	0.95	2.54	3.253 (2)	132
C15—H15···O2ⁱⁱⁱ	0.95	2.52	3.294 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂FIO₃S
M_r	430.22
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.5839 (2), 10.2443 (3), 10.4651 (3)
α, β, γ (°)	79.424 (1), 75.652 (1), 80.361 (1)
V (Å³)	767.94 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.24
Crystal size (mm)	0.32 × 0.30 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.534, 0.689
No. of measured, independent and observed [I > 2σ(I)] reflections	13962, 3785, 3585
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.057, 1.08
No. of reflections	3785
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.72

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
C12—H12···O3ⁱ	0.95	2.54	3.253 (2)	132.4
C15—H15···O2ⁱⁱ	0.95	2.52	3.294 (3)	139.0

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

References

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Volume 68| Part 1| January 2012| Page o96

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