4-(4-Cyano-2-fluoro-phen-oxy)phenyl 4-methyl-benzene-sulfonate.

The title compound, C(20)H(14)FNO(4)S, was synthesized from hydro-quinone, p-toluene-sulfonyl chloride and 3,4-difluoro-benzonitrile. A folded conformation is adopted by the crystal structure. Inter-molecular 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 = 383.39

Triclinic,

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 F 2 > 2σ(F 2)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.123

S = 1.01

4114 reflections

245 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.50 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H14FNO4S	Z = 2
Mr = 383.39	F(000) = 396.00
Triclinic, P1	Dx = 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

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

Refinement on F2	w = 1/[0.0006Fo2 + 2σ(Fo2)]/(4Fo2)
R[F2 > 2σ(F2)] = 0.041	(Δ/σ)max < 0.001
wR(F2) = 0.123	Δρmax = 0.46 e Å−3
S = 1.01	Δρmin = −0.50 e Å−3
4114 reflections	Extinction correction: Larson (1970)
245 parameters	Extinction coefficient: 591 (29)
H-atom parameters constrained

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).

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .