4-(4-Cyano-2-fluoro­phen­oxy)phenyl 4-methyl­benzene­sulfonate

Luo, S.; Zhang, J.; Wang, J.; Li, B.

doi:10.1107/S1600536809029201

organic compounds

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Volume 65| Part 8| August 2009| Page o2011

doi:10.1107/S1600536809029201

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4-(4-Cyano-2-fluorophenoxy)phenyl 4-methylbenzenesulfonate

Shuping Luo,^a ^* Jixu Zhang,^a Jianfeng Wang ^a and Bailin Li ^a

^aState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: lsp96@163.com

(Received 13 July 2009; accepted 23 July 2009; online 29 July 2009)

The title compound, C₂₀H₁₄FNO₄S, was synthesized from hydroquinone, p-toluenesulfonyl chloride and 3,4-difluorobenzonitrile. A folded conformation is adopted by the crystal structure. Intermolecular C—H⋯N hydrogen bonds form dimers arranged around inversion centers.

Related literature

For the herbicidal activity of hydroquinone derivatives, see: Bao et al. (2007 ); Liu (2002 ). For related structures, see: Chen & Zhang (2009 ); Han et al. (2008 ); Yang et al. (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ); Etter (1990 ).

Experimental

Crystal data

C₂₀H₁₄FNO₄S
M_r = 383.39
Triclinic, $[P \overline 1]$
a = 7.5504 (4) Å
b = 9.9558 (6) Å
c = 12.5862 (6) Å
α = 89.5250 (15)°
β = 77.8080 (12)°
γ = 81.9370 (15)°
V = 915.40 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.42 × 0.32 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.910, T_max = 0.942
9012 measured reflections
4114 independent reflections
2386 reflections with F² > 2σ(F²)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.123
S = 1.01
4114 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯N1ⁱ	0.93	2.61	3.461 (3)	152
Symmetry code: (i) -x+2, -y, -z+2.

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ), and Larson (1970 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: CrystalStructure.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809029201/dn2473sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029201/dn2473Isup2.hkl

checkCIF report

Comment top

The herbicidal activity of hydroquinone derivatives is well known in the art (Liu, 2002. Bao et al., 2007). As part of our ongoing studies, we now describe the synthesis and the crystal structure of the title compound.

As shown in Fig.1, the terminal C1—C7/S1 phenyl ring, the central benzene ring (C8—C13/O3/O4) and the other terminal phenyl ring (C14—C20/N1) form three planes, with max deviations for fitted atoms of 0.042 Å, 0.022Å and 0.013 Å, respectively. These planes make dihedral angles of 45.0 (1)° and 64.6 (6)° respectively. Otherwise, the molecule is bent at the sulfonate group with the C1—S1—O3—C8 torsion angle of 50.7 (3). The other bond parameters are similar to those observed in 4-Methyl-2-oxo-2,3-dihydro-1-benzopyran-7-yl benzenesulfonate (Yang et al., 2008), (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) iminomethyl]phenyl 4-bromobenzenesulfonate (Han et al., 2008) and 2-Methyl-3-nitrobenzyl cyanide (Chen et al., 2009).

In the crystal structure, the molecules are linked to form pseudo dimers by inter molecular C—H···N hydrogen bonds generating a graph set motif R₂²(10) (Table 1, Fig.2) (Etter, 1990, Bernstein et al., 1995). In addition, the structure is stabilized by weak C—H···O and van der Waal's interactions.

Related literature top

For the herbicidal activity of hydroquinone derivatives, see: Bao et al. (2007); Liu (2002). For related structures, see: Chen & Zhang (2009); Han et al. (2008); Yang et al. (2008). Forhydrogen-bond motifs, see: Bernstein et al. (1995); Etter (1990).

Experimental top

A DMSO (10 ml) solution of hydroquinone and p-toluenesulfonyl chloride in the presence of KOH as base was stirred at room temperature for 48 h. Then the mixture was heated to 70°C and 3,4-difluorobenzonitrile was added dropwise. Finally the mixture was washed with water (20 ml) and extracted with ethyl acetate (three times). The organic solvent was removed under reduced pressure and the product was purified by silica gel chromatography (pentane: ethyl acetate mixtures). Suitable crystals were obtained by slow evaporation of ethanol at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004), and Larson (1970); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2004).

Figures top

	Fig. 1. Molecular structure of title compound, with the atomic labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of title compound. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x+2, -y, -z+2].

4-(4-Cyano-2-fluorophenoxy)phenyl 4-methylbenzenesulfonate top

Crystal data top

C₂₀H₁₄FNO₄S	Z = 2
M_r = 383.39	F(000) = 396.00
Triclinic, P1	D_x = 1.391 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71075 Å
a = 7.5504 (4) Å	Cell parameters from 5883 reflections
b = 9.9558 (6) Å	θ = 3.2–27.4°
c = 12.5862 (6) Å	µ = 0.21 mm⁻¹
α = 89.5250 (15)°	T = 296 K
β = 77.8080 (12)°	Chunk, colorless
γ = 81.9370 (15)°	0.42 × 0.32 × 0.28 mm
V = 915.40 (9) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2386 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.025
ω scans	θ_max = 27.4°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→9
T_min = 0.910, T_max = 0.942	k = −12→12
9012 measured reflections	l = −16→16
4114 independent reflections

Refinement top

Refinement on F²	w = 1/[0.0006F_o² + 2σ(F_o²)]/(4F_o²)
R[F² > 2σ(F²)] = 0.041	(Δ/σ)_max < 0.001
wR(F²) = 0.123	Δρ_max = 0.46 e Å⁻³
S = 1.01	Δρ_min = −0.50 e Å⁻³
4114 reflections	Extinction correction: Larson (1970)
245 parameters	Extinction coefficient: 591 (29)
H-atom parameters constrained

Crystal data top

C₂₀H₁₄FNO₄S	γ = 81.9370 (15)°
M_r = 383.39	V = 915.40 (9) Å³
Triclinic, P1	Z = 2
a = 7.5504 (4) Å	Mo Kα radiation
b = 9.9558 (6) Å	µ = 0.21 mm⁻¹
c = 12.5862 (6) Å	T = 296 K
α = 89.5250 (15)°	0.42 × 0.32 × 0.28 mm
β = 77.8080 (12)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4114 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2386 reflections with F² > 2σ(F²)
T_min = 0.910, T_max = 0.942	R_int = 0.025
9012 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	245 parameters
wR(F²) = 0.123	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
4114 reflections	Δρ_min = −0.50 e Å⁻³

Special details top

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
S1	0.16109 (6)	0.69907 (6)	0.48722 (4)	0.05510 (18)
F1	0.3393 (2)	0.2172 (2)	1.07043 (12)	0.1276 (7)
O1	0.0493 (2)	0.78677 (14)	0.43051 (12)	0.0702 (5)
O2	0.2714 (2)	0.58197 (13)	0.43277 (12)	0.0653 (4)
O3	0.01598 (18)	0.65207 (16)	0.58710 (12)	0.0606 (4)
O4	0.2671 (2)	0.4109 (2)	0.93536 (12)	0.0767 (6)
N1	1.1212 (3)	0.0868 (3)	0.8909 (2)	0.1196 (11)
C1	0.2945 (2)	0.7893 (2)	0.54964 (16)	0.0488 (6)
C2	0.4542 (2)	0.7240 (2)	0.57449 (19)	0.0607 (7)
C3	0.5538 (2)	0.7947 (2)	0.6284 (2)	0.0670 (8)
C4	0.4972 (3)	0.9299 (2)	0.65809 (18)	0.0635 (7)
C5	0.3378 (3)	0.9927 (2)	0.63241 (19)	0.0680 (7)
C6	0.2358 (3)	0.9238 (2)	0.57855 (18)	0.0604 (7)
C7	0.6053 (4)	1.0073 (3)	0.7184 (2)	0.0936 (10)
C8	0.0820 (2)	0.5862 (2)	0.67430 (18)	0.0522 (6)
C9	0.1745 (2)	0.4561 (2)	0.66080 (18)	0.0554 (6)
C10	0.2391 (2)	0.3966 (2)	0.74779 (18)	0.0613 (7)
C11	0.2089 (2)	0.4676 (2)	0.84456 (18)	0.0614 (7)
C12	0.1107 (3)	0.5944 (2)	0.8574 (2)	0.0739 (8)
C13	0.0470 (3)	0.6553 (2)	0.7708 (2)	0.0704 (8)
C14	0.4443 (3)	0.3479 (2)	0.92161 (17)	0.0645 (7)
C15	0.4799 (3)	0.2471 (3)	0.99270 (19)	0.0762 (8)
C16	0.6506 (3)	0.1772 (2)	0.98788 (19)	0.0780 (8)
C17	0.7936 (3)	0.2105 (2)	0.90833 (18)	0.0687 (8)
C18	0.7627 (3)	0.3131 (2)	0.8374 (2)	0.0742 (8)
C19	0.5882 (3)	0.3820 (2)	0.84441 (19)	0.0716 (8)
C20	0.9752 (3)	0.1401 (3)	0.8989 (2)	0.0856 (10)
H2	0.4940	0.6332	0.5550	0.073*
H3	0.6611	0.7507	0.6452	0.080*
H5	0.2980	1.0836	0.6518	0.082*
H6	0.1283	0.9677	0.5619	0.072*
H9	0.1932	0.4093	0.5949	0.066*
H10	0.3026	0.3090	0.7407	0.074*
H12	0.0867	0.6399	0.9243	0.089*
H13	−0.0188	0.7421	0.7786	0.085*
H16	0.6703	0.1090	1.0368	0.094*
H18	0.8594	0.3360	0.7847	0.089*
H19	0.5681	0.4516	0.7968	0.086*
H71	0.5630	0.9986	0.7953	0.112*
H72	0.5889	1.1014	0.7001	0.112*
H73	0.7328	0.9711	0.6981	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0528 (3)	0.0515 (3)	0.0600 (3)	0.0018 (2)	−0.0156 (2)	0.0017 (2)
F1	0.0771 (10)	0.191 (2)	0.0934 (11)	0.0040 (11)	0.0113 (9)	0.0689 (12)
O1	0.0738 (10)	0.0636 (11)	0.0790 (10)	0.0040 (8)	−0.0384 (9)	0.0084 (8)
O2	0.0729 (10)	0.0498 (10)	0.0666 (9)	0.0062 (8)	−0.0093 (8)	−0.0106 (7)
O3	0.0409 (7)	0.0681 (10)	0.0715 (9)	−0.0008 (7)	−0.0141 (7)	0.0079 (8)
O4	0.0641 (10)	0.1006 (16)	0.0548 (9)	0.0083 (10)	−0.0018 (7)	0.0114 (9)
N1	0.0747 (17)	0.165 (2)	0.1032 (19)	0.0130 (18)	−0.0039 (14)	0.0380 (19)
C1	0.0450 (11)	0.0443 (13)	0.0541 (11)	0.0034 (9)	−0.0102 (9)	0.0015 (9)
C2	0.0450 (12)	0.0501 (14)	0.0829 (15)	0.0025 (11)	−0.0104 (11)	−0.0006 (12)
C3	0.0465 (12)	0.0709 (18)	0.0860 (17)	−0.0043 (12)	−0.0224 (12)	0.0092 (14)
C4	0.0649 (15)	0.0703 (18)	0.0600 (13)	−0.0209 (13)	−0.0165 (11)	0.0107 (12)
C5	0.0849 (17)	0.0489 (15)	0.0714 (15)	−0.0026 (13)	−0.0239 (13)	−0.0035 (12)
C6	0.0632 (14)	0.0500 (15)	0.0671 (14)	0.0072 (12)	−0.0217 (11)	−0.0003 (11)
C7	0.104 (2)	0.102 (2)	0.0925 (19)	−0.0405 (19)	−0.0434 (17)	0.0119 (17)
C8	0.0375 (10)	0.0554 (14)	0.0617 (13)	−0.0048 (10)	−0.0070 (9)	0.0044 (11)
C9	0.0535 (12)	0.0537 (14)	0.0606 (13)	−0.0104 (11)	−0.0140 (10)	−0.0015 (11)
C10	0.0568 (13)	0.0537 (15)	0.0693 (15)	−0.0022 (11)	−0.0078 (11)	0.0036 (12)
C11	0.0494 (13)	0.0771 (18)	0.0532 (13)	−0.0028 (12)	−0.0047 (10)	0.0063 (12)
C12	0.0739 (16)	0.082 (2)	0.0560 (14)	0.0051 (15)	−0.0019 (12)	−0.0138 (13)
C13	0.0649 (15)	0.0649 (17)	0.0692 (15)	0.0126 (13)	−0.0006 (12)	−0.0062 (13)
C14	0.0558 (14)	0.0872 (19)	0.0487 (12)	−0.0056 (13)	−0.0100 (11)	0.0058 (12)
C15	0.0596 (15)	0.109 (2)	0.0517 (13)	−0.0074 (15)	0.0026 (12)	0.0185 (14)
C16	0.0692 (16)	0.100 (2)	0.0597 (14)	−0.0042 (15)	−0.0077 (13)	0.0218 (14)
C17	0.0581 (14)	0.091 (2)	0.0558 (13)	−0.0062 (13)	−0.0126 (11)	0.0020 (13)
C18	0.0587 (15)	0.106 (2)	0.0598 (14)	−0.0209 (14)	−0.0108 (11)	0.0124 (14)
C19	0.0630 (15)	0.092 (2)	0.0617 (14)	−0.0169 (14)	−0.0156 (12)	0.0184 (13)
C20	0.0653 (17)	0.119 (2)	0.0667 (16)	0.0003 (17)	−0.0093 (14)	0.0178 (16)

Geometric parameters (Å, º) top

S1—O1	1.4220 (16)	C14—C15	1.376 (3)
S1—O2	1.4221 (13)	C14—C19	1.375 (3)
S1—O3	1.5975 (14)	C15—C16	1.366 (3)
S1—C1	1.744 (2)	C16—C17	1.384 (3)
F1—C15	1.348 (2)	C17—C18	1.379 (3)
O3—C8	1.418 (2)	C17—C20	1.431 (3)
O4—C11	1.397 (2)	C18—C19	1.383 (3)
O4—C14	1.371 (2)	C2—H2	0.930
N1—C20	1.139 (3)	C3—H3	0.930
C1—C2	1.382 (2)	C5—H5	0.930
C1—C6	1.377 (3)	C6—H6	0.930
C2—C3	1.375 (3)	C7—H71	0.960
C3—C4	1.384 (3)	C7—H72	0.960
C4—C5	1.376 (3)	C7—H73	0.960
C4—C7	1.511 (4)	C9—H9	0.930
C5—C6	1.378 (3)	C10—H10	0.930
C8—C9	1.376 (3)	C12—H12	0.930
C8—C13	1.359 (3)	C13—H13	0.930
C9—C10	1.386 (3)	C16—H16	0.930
C10—C11	1.374 (3)	C18—H18	0.930
C11—C12	1.363 (3)	C19—H19	0.930
C12—C13	1.384 (3)

O1—S1—O2	119.42 (9)	C16—C17—C18	120.1 (2)
O1—S1—O3	102.89 (8)	C16—C17—C20	120.8 (2)
O1—S1—C1	111.32 (10)	C18—C17—C20	119.1 (2)
O2—S1—O3	108.85 (8)	C17—C18—C19	120.2 (2)
O2—S1—C1	109.48 (9)	C14—C19—C18	120.2 (2)
O3—S1—C1	103.47 (8)	N1—C20—C17	178.4 (3)
S1—O3—C8	118.35 (12)	C1—C2—H2	120.3
C11—O4—C14	118.07 (15)	C3—C2—H2	120.3
S1—C1—C2	119.91 (17)	C2—C3—H3	119.4
S1—C1—C6	119.74 (16)	C4—C3—H3	119.4
C2—C1—C6	120.3 (2)	C4—C5—H5	119.3
C1—C2—C3	119.4 (2)	C6—C5—H5	119.3
C2—C3—C4	121.2 (2)	C1—C6—H6	120.3
C3—C4—C5	118.3 (2)	C5—C6—H6	120.3
C3—C4—C7	121.3 (2)	C4—C7—H71	109.5
C5—C4—C7	120.4 (2)	C4—C7—H72	109.5
C4—C5—C6	121.4 (2)	C4—C7—H73	109.5
C1—C6—C5	119.4 (2)	H71—C7—H72	109.5
O3—C8—C9	120.46 (19)	H71—C7—H73	109.5
O3—C8—C13	117.51 (19)	H72—C7—H73	109.5
C9—C8—C13	122.0 (2)	C8—C9—H9	120.8
C8—C9—C10	118.4 (2)	C10—C9—H9	120.8
C9—C10—C11	119.7 (2)	C9—C10—H10	120.1
O4—C11—C10	121.9 (2)	C11—C10—H10	120.1
O4—C11—C12	117.2 (2)	C11—C12—H12	120.1
C10—C11—C12	120.8 (2)	C13—C12—H12	120.1
C11—C12—C13	119.9 (2)	C8—C13—H13	120.5
C8—C13—C12	119.0 (2)	C12—C13—H13	120.5
O4—C14—C15	117.19 (19)	C15—C16—H16	120.9
O4—C14—C19	124.5 (2)	C17—C16—H16	120.9
C15—C14—C19	118.3 (2)	C17—C18—H18	119.9
F1—C15—C14	118.0 (2)	C19—C18—H18	119.9
F1—C15—C16	119.1 (2)	C14—C19—H19	119.9
C14—C15—C16	122.9 (2)	C18—C19—H19	119.9
C15—C16—C17	118.3 (2)

O1—S1—O3—C8	−166.73 (15)	C4—C5—C6—C1	−0.1 (2)
O1—S1—C1—C2	−156.85 (16)	O3—C8—C9—C10	178.99 (19)
O1—S1—C1—C6	26.20 (19)	O3—C8—C13—C12	−179.5 (2)
O2—S1—O3—C8	65.64 (17)	C9—C8—C13—C12	1.9 (3)
O2—S1—C1—C2	−22.63 (19)	C13—C8—C9—C10	−2.4 (3)
O2—S1—C1—C6	160.42 (16)	C8—C9—C10—C11	0.3 (3)
O3—S1—C1—C2	93.29 (17)	C9—C10—C11—O4	178.3 (2)
O3—S1—C1—C6	−83.66 (17)	C9—C10—C11—C12	2.2 (3)
C1—S1—O3—C8	−50.73 (17)	O4—C11—C12—C13	−179.1 (2)
S1—O3—C8—C9	−71.2 (2)	C10—C11—C12—C13	−2.8 (3)
S1—O3—C8—C13	110.10 (19)	C11—C12—C13—C8	0.8 (3)
C11—O4—C14—C15	−153.2 (2)	O4—C14—C15—F1	0.0 (3)
C11—O4—C14—C19	29.1 (3)	O4—C14—C15—C16	−179.7 (2)
C14—O4—C11—C10	48.8 (3)	O4—C14—C19—C18	179.5 (2)
C14—O4—C11—C12	−134.9 (2)	C15—C14—C19—C18	1.8 (4)
S1—C1—C2—C3	−176.91 (16)	C19—C14—C15—F1	177.9 (2)
S1—C1—C6—C5	176.99 (16)	C19—C14—C15—C16	−1.9 (4)
C2—C1—C6—C5	0.1 (2)	F1—C15—C16—C17	−179.2 (2)
C6—C1—C2—C3	0.0 (2)	C14—C15—C16—C17	0.5 (4)
C1—C2—C3—C4	−0.1 (2)	C15—C16—C17—C18	0.9 (4)
C2—C3—C4—C5	0.0 (2)	C15—C16—C17—C20	−179.6 (2)
C2—C3—C4—C7	179.3 (2)	C16—C17—C18—C19	−0.9 (4)
C3—C4—C5—C6	0.0 (2)	C20—C17—C18—C19	179.6 (2)
C7—C4—C5—C6	−179.3 (2)	C17—C18—C19—C14	−0.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1ⁱ	0.93	2.61	3.461 (3)	152

Symmetry code: (i) −x+2, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₄FNO₄S
M_r	383.39
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.5504 (4), 9.9558 (6), 12.5862 (6)
α, β, γ (°)	89.5250 (15), 77.8080 (12), 81.9370 (15)
V (Å³)	915.40 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.42 × 0.32 × 0.28

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.910, 0.942
No. of measured, independent and observed [F² > 2σ(F²)] reflections	9012, 4114, 2386
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.123, 1.01
No. of reflections	4114
No. of parameters	245
No. of restraints	?
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.50

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), and Larson (1970), SHELXS97 (Sheldrick, 2008), CRYSTALS (Betteridge et al., 2003), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), CrystalStructure (Rigaku/MSC, 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···N1ⁱ	0.9300	2.6100	3.461 (3)	152.00

Symmetry code: (i) −x+2, −y, −z+2.

References

Bao, W. J., Wu, Y. G., Mao, C. H., Chen, M. & Huang, M. Z. (2007). Fine Chem. Interm. 37, 9–13. CAS Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J. (2003). J. Appl. Cryst. 36, 1487. Web of Science CrossRef IUCr Journals Google Scholar
Chen, Y.-S. & Zhang, J.-H. (2009). Acta Cryst. E65, o767. Web of Science CSD CrossRef IUCr Journals Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Han, J.-R., Tian, X., Zhen, X.-L., Li, Z.-C. & Liu, S.-X. (2008). Acta Cryst. E64, o2244. Web of Science CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Larson, A. C. (1970). Crystallographic Computing, edited by F. R. Ahmed, S. R. Hall & C. P. Huber, pp. 291–294. Copenhagen: Munksgaard. Google Scholar
Liu, C. L. (2002). Pesticides, 41, 38. Google Scholar
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, S.-P., Wang, D.-Q., Han, L.-J. & Liu, Y.-F. (2008). Acta Cryst. E64, o2088. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 8| August 2009| Page o2011

doi:10.1107/S1600536809029201

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