Viox, a COX-II inhibitor

Viox {2,5-di­hydro-4-[4-(methyl­sulfonyl)­phenyl]-3-phenyl-2-furan­one, C₁₇H₁₄O₄S, (I)} is one of the selective COX-II inhibitors with anti-arthritic activity. The absolute structure of viox has been determined on the basis of anomalous scattering effects. Molecules are held together in the crystal structure only by normal van der Waals interactions.

S1. Experimental

Crystals suitable for diffraction analysis were obtained by slow evaporation of an acetonitrile solution.

S2. Refinement

The absolute structure was determined by refining the reported structure and the inverted form in space group P4₃2₁2; the alternative model gave R = 0.0512, wR = 0.0726, S = 2.14 for the same number of data and parameters, and so can be rejected as incorrect.

Computing details

Data collection: MSC/AFC Diffractometer Control Software (MSC, 1993); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (MSC, 1992-1997); program(s) used to refine structure: TEXSAN (MSC, 1992-1997); software used to prepare material for publication: TEXSAN (MSC, 1992-1997).

4-(4-methylsulfonylphenyl)-3-phenyl-2,5-dihydro-2-furanone

Crystal data

C17H14O4S	Dx = 1.407 Mg m^−3
Mr = 314.36	Cu Kα radiation, λ = 1.5418 Å
Tetragonal, P41212	Cell parameters from 25 reflections
a = 11.374 (2) Å	θ = 21.1–29.1°
c = 22.939 (3) Å	µ = 2.08 mm^−1
V = 2967.6 (9) Å^3	T = 298 K
Z = 8	Block, yellow
F(000) = 1312.00	0.50 × 0.50 × 0.30 mm

Data collection

Rigaku AFC-7S diffractometer	1656 reflections with I > 0
Radiation source: X-ray tube	Rint = 0.000
Graphite monochromator	θmax = 70.1°, θmin = 3.9°
ω–2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→9
Tmin = 0.390, Tmax = 0.535	l = 0→26
1682 measured reflections	3 standard reflections every 150 reflections
1682 independent reflections	intensity decay: 0.4%

Refinement

Refinement on F	0 constraints
Least-squares matrix: full	H-atom parameters not refined
R[F^2 > 2σ(F^2)] = 0.042	Weighting scheme based on measured s.u.'s w = 1/[σ^2(Fo) + 0.00063|Fo|^2]
wR(F^2) = 0.059	(Δ/σ)max = 0.005
S = 1.74	Δρmax = 0.23 e Å^−3
1656 reflections	Δρmin = −0.36 e Å^−3
200 parameters	Extinction correction: Zachariasen (1967), equation 3, Acta Cryst. (1968). A24, 213.
0 restraints	Extinction coefficient: 1.22E-5 (9)

Special details

Experimental. The scan width was (0.58 + 0.14tanθ)° with an ω scan speed of 0° per minute (up to 9 scans to achieve I/σ(I) > 15). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S(1)	0.35342 (5)	−0.38417 (5)	0.87720 (2)	0.0513 (2)
O(1)	0.3495 (3)	0.2797 (2)	0.7440 (1)	0.0878 (8)
O(2)	0.5064 (3)	0.3277 (2)	0.6905 (1)	0.108 (1)
O(3)	0.4527 (2)	−0.3909 (2)	0.91551 (8)	0.0694 (6)
O(4)	0.2377 (2)	−0.3938 (2)	0.90181 (9)	0.0734 (7)
C(1)	0.6892 (3)	0.1130 (4)	0.7060 (1)	0.085 (1)
C(2)	0.7860 (4)	0.0614 (5)	0.6820 (2)	0.100 (1)
C(3)	0.7747 (4)	−0.0355 (4)	0.6457 (2)	0.096 (1)
C(4)	0.6636 (4)	−0.0784 (3)	0.6334 (2)	0.080 (1)
C(5)	0.5661 (3)	−0.0258 (3)	0.6579 (1)	0.0632 (8)
C(6)	0.5778 (3)	0.0703 (2)	0.6943 (1)	0.0579 (7)
C(7)	0.4750 (3)	0.1258 (2)	0.7217 (1)	0.0593 (7)
C(8)	0.4502 (4)	0.2538 (3)	0.7156 (2)	0.078 (1)
C(9)	0.3046 (3)	0.1748 (3)	0.7707 (1)	0.0719 (9)
C(10)	0.3909 (2)	0.0800 (2)	0.7551 (1)	0.0525 (7)
C(11)	0.3796 (2)	−0.0379 (2)	0.7801 (1)	0.0474 (6)
C(12)	0.4799 (2)	−0.1056 (2)	0.7909 (1)	0.0478 (6)
C(13)	0.4708 (2)	−0.2112 (2)	0.8202 (1)	0.0474 (6)
C(14)	0.3615 (2)	−0.2510 (2)	0.8387 (1)	0.0470 (6)
C(15)	0.2608 (2)	−0.1862 (3)	0.8272 (1)	0.0580 (7)
C(16)	0.2704 (2)	−0.0800 (3)	0.7982 (1)	0.0576 (7)
C(17)	0.3703 (3)	−0.4915 (3)	0.8232 (1)	0.0633 (8)
H(1)	0.6973	0.1841	0.7311	0.089*
H(2)	0.8661	0.0919	0.6942	0.106*
H(3)	0.8447	−0.0664	0.6303	0.103*
H(4)	0.6594	−0.1426	0.6080	0.088*
H(5)	0.4898	−0.0582	0.6504	0.067*
H(6)	0.5554	−0.0774	0.7779	0.049*
H(7)	0.5395	−0.2581	0.8261	0.049*
H(8)	0.1871	−0.2132	0.8398	0.061*
H(9)	0.1993	−0.0324	0.7913	0.058*
H(10)	0.3612	−0.5707	0.8382	0.070*
H(11)	0.3124	−0.4836	0.7921	0.070*
H(12)	0.4464	−0.4887	0.8045	0.070*
H(13)	0.2975	0.1837	0.8122	0.077*
H(14)	0.2266	0.1562	0.7561	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S(1)	0.0503 (4)	0.0537 (3)	0.0498 (4)	−0.0071 (2)	0.0017 (2)	0.0050 (3)
O(1)	0.116 (2)	0.047 (1)	0.100 (2)	0.016 (1)	−0.014 (2)	−0.001 (1)
O(2)	0.161 (3)	0.051 (1)	0.112 (2)	−0.022 (2)	−0.006 (2)	0.023 (1)
O(3)	0.072 (1)	0.074 (1)	0.062 (1)	−0.010 (1)	−0.016 (1)	0.014 (1)
O(4)	0.066 (1)	0.077 (2)	0.078 (1)	−0.011 (1)	0.025 (1)	0.010 (1)
C(1)	0.078 (2)	0.100 (3)	0.077 (2)	−0.037 (2)	0.008 (2)	−0.008 (2)
C(2)	0.073 (2)	0.133 (4)	0.093 (2)	−0.035 (2)	0.016 (2)	−0.004 (3)
C(3)	0.084 (3)	0.111 (3)	0.092 (2)	0.001 (2)	0.032 (2)	0.034 (2)
C(4)	0.103 (3)	0.066 (2)	0.072 (2)	0.000 (2)	0.020 (2)	0.008 (2)
C(5)	0.076 (2)	0.054 (1)	0.060 (1)	−0.009 (1)	−0.002 (1)	0.005 (1)
C(6)	0.071 (2)	0.051 (1)	0.052 (1)	−0.017 (1)	−0.004 (1)	0.007 (1)
C(7)	0.076 (2)	0.044 (1)	0.058 (1)	−0.008 (1)	−0.016 (1)	0.003 (1)
C(8)	0.114 (3)	0.045 (2)	0.074 (2)	−0.010 (2)	−0.017 (2)	0.006 (1)
C(9)	0.082 (2)	0.053 (2)	0.081 (2)	0.017 (2)	−0.010 (2)	−0.006 (1)
C(10)	0.060 (1)	0.047 (1)	0.051 (1)	0.003 (1)	−0.011 (1)	−0.003 (1)
C(11)	0.047 (1)	0.046 (1)	0.049 (1)	0.002 (1)	−0.003 (1)	−0.004 (1)
C(12)	0.040 (1)	0.049 (1)	0.054 (1)	−0.0025 (9)	0.000 (1)	0.004 (1)
C(13)	0.037 (1)	0.050 (1)	0.055 (1)	0.0017 (9)	−0.002 (1)	0.003 (1)
C(14)	0.045 (1)	0.048 (1)	0.048 (1)	−0.002 (1)	0.001 (1)	−0.001 (1)
C(15)	0.038 (1)	0.067 (2)	0.069 (2)	0.001 (1)	0.006 (1)	0.006 (1)
C(16)	0.043 (1)	0.060 (2)	0.070 (2)	0.006 (1)	−0.001 (1)	0.003 (1)
C(17)	0.073 (2)	0.053 (1)	0.064 (2)	−0.001 (1)	−0.003 (1)	0.000 (1)

Geometric parameters (Å, º)

S(1)—O(3)	1.433 (2)	C(7)—C(8)	1.490 (4)
S(1)—O(4)	1.436 (2)	C(7)—C(10)	1.331 (4)
S(1)—C(14)	1.756 (3)	C(9)—C(10)	1.502 (4)
S(1)—C(17)	1.749 (3)	C(9)—H(13)	0.96
O(1)—C(8)	1.350 (5)	C(9)—H(14)	0.97
O(1)—C(9)	1.434 (4)	C(10)—C(11)	1.465 (3)
O(2)—C(8)	1.202 (4)	C(11)—C(12)	1.398 (3)
C(1)—C(2)	1.365 (6)	C(11)—C(16)	1.394 (4)
C(1)—C(6)	1.383 (4)	C(12)—C(13)	1.380 (3)
C(1)—H(1)	1.00	C(12)—H(6)	0.96
C(2)—C(3)	1.388 (7)	C(13)—C(14)	1.390 (3)
C(2)—H(2)	1.01	C(13)—H(7)	0.96
C(3)—C(4)	1.383 (6)	C(14)—C(15)	1.387 (4)
C(3)—H(3)	0.94	C(15)—C(16)	1.384 (4)
C(4)—C(5)	1.381 (5)	C(15)—H(8)	0.94
C(4)—H(4)	0.93	C(16)—H(9)	0.99
C(5)—C(6)	1.382 (4)	C(17)—H(10)	0.97
C(5)—H(5)	0.96	C(17)—H(11)	0.98
C(6)—C(7)	1.470 (5)	C(17)—H(12)	0.97
O(1)···H(10)^i	2.7521	O(4)···H(14)^v	3.0082
O(1)···H(7)^ii	2.8096	O(4)···C(12)^ix	3.213 (3)
O(1)···H(11)^i	2.9404	O(4)···C(13)^ix	3.324 (3)
O(1)···C(17)^i	3.183 (4)	O(4)···C(5)^viii	3.395 (4)
O(1)···O(4)^iii	3.489 (4)	C(1)···H(1)^x	2.9683
O(1)···C(13)^ii	3.563 (3)	C(2)···H(10)^xi	2.8400
O(2)···H(12)^ii	2.5808	C(3)···H(10)^xi	2.9596
O(2)···H(3)^iv	2.6392	C(5)···C(12)^iii	3.359 (4)
O(2)···C(17)^ii	3.454 (4)	C(5)···C(11)^iii	3.571 (4)
O(2)···C(3)^iv	3.541 (5)	C(8)···C(15)^iii	3.536 (5)
O(2)···C(15)^iii	3.544 (4)	C(12)···H(5)^v	2.8769
O(2)···C(16)^iii	3.588 (4)	C(12)···H(11)^viii	3.0270
O(3)···H(14)^v	2.7627	C(13)···H(11)^viii	2.8255
O(3)···H(2)^vi	2.8860	H(1)···H(1)^x	2.0947
O(3)···H(8)^vii	2.9208	H(2)···H(10)^xi	2.5917
O(3)···C(9)^v	3.587 (4)	H(2)···H(2)^x	2.6478
O(4)···H(5)^viii	2.6062	H(7)···H(8)^vii	2.5788
O(4)···H(6)^ix	2.6462	H(12)···H(12)^viii	2.5900
O(4)···H(7)^ix	2.8852
O(3)—S(1)—O(4)	118.5 (1)	O(1)—C(9)—H(13)	111.4
O(3)—S(1)—C(14)	108.3 (1)	O(1)—C(9)—H(14)	111.1
O(3)—S(1)—C(17)	108.1 (1)	C(10)—C(9)—H(13)	111.5
O(4)—S(1)—C(14)	108.1 (1)	C(10)—C(9)—H(14)	111.0
O(4)—S(1)—C(17)	109.0 (1)	H(13)—C(9)—H(14)	106.7
C(14)—S(1)—C(17)	103.9 (1)	C(7)—C(10)—C(9)	109.0 (3)
C(8)—O(1)—C(9)	109.1 (2)	C(7)—C(10)—C(11)	130.3 (3)
C(2)—C(1)—C(6)	120.6 (3)	C(9)—C(10)—C(11)	120.4 (3)
C(2)—C(1)—H(1)	120.5	C(10)—C(11)—C(12)	120.1 (2)
C(6)—C(1)—H(1)	118.8	C(10)—C(11)—C(16)	120.6 (2)
C(1)—C(2)—C(3)	120.6 (4)	C(12)—C(11)—C(16)	119.0 (2)
C(1)—C(2)—H(2)	117.8	C(11)—C(12)—C(13)	120.3 (2)
C(3)—C(2)—H(2)	121.4	C(11)—C(12)—H(6)	119.3
C(2)—C(3)—C(4)	119.2 (4)	C(13)—C(12)—H(6)	120.4
C(2)—C(3)—H(3)	116.3	C(12)—C(13)—C(14)	119.9 (2)
C(4)—C(3)—H(3)	124.4	C(12)—C(13)—H(7)	119.6
C(3)—C(4)—C(5)	119.8 (4)	C(14)—C(13)—H(7)	120.4
C(3)—C(4)—H(4)	116.8	S(1)—C(14)—C(13)	118.8 (2)
C(5)—C(4)—H(4)	123.4	S(1)—C(14)—C(15)	120.7 (2)
C(4)—C(5)—C(6)	120.8 (3)	C(13)—C(14)—C(15)	120.5 (2)
C(4)—C(5)—H(5)	119.1	C(14)—C(15)—C(16)	119.4 (2)
C(6)—C(5)—H(5)	120.0	C(14)—C(15)—H(8)	120.3
C(1)—C(6)—C(5)	119.0 (3)	C(16)—C(15)—H(8)	120.3
C(1)—C(6)—C(7)	119.6 (3)	C(11)—C(16)—C(15)	120.9 (2)
C(5)—C(6)—C(7)	121.4 (3)	C(11)—C(16)—H(9)	119.6
C(6)—C(7)—C(8)	122.1 (3)	C(15)—C(16)—H(9)	119.5
C(6)—C(7)—C(10)	130.5 (3)	S(1)—C(17)—H(10)	112.8
C(8)—C(7)—C(10)	107.4 (3)	S(1)—C(17)—H(11)	112.3
O(1)—C(8)—O(2)	122.0 (3)	S(1)—C(17)—H(12)	113.0
O(1)—C(8)—C(7)	109.2 (3)	H(10)—C(17)—H(11)	105.8
O(2)—C(8)—C(7)	128.8 (4)	H(10)—C(17)—H(12)	106.4
O(1)—C(9)—C(10)	105.2 (3)	H(11)—C(17)—H(12)	106.0
S(1)—C(14)—C(13)—C(12)	−178.6 (2)	C(5)—C(6)—C(7)—C(8)	−125.6 (3)
S(1)—C(14)—C(15)—C(16)	178.3 (2)	C(5)—C(6)—C(7)—C(10)	55.4 (4)
O(1)—C(8)—C(7)—C(6)	178.7 (2)	C(6)—C(7)—C(10)—C(9)	−178.8 (3)
O(1)—C(8)—C(7)—C(10)	−2.1 (3)	C(6)—C(7)—C(10)—C(11)	6.8 (5)
O(1)—C(9)—C(10)—C(7)	−1.4 (3)	C(7)—C(8)—O(1)—C(9)	1.2 (4)
O(1)—C(9)—C(10)—C(11)	173.6 (2)	C(7)—C(10)—C(11)—C(12)	25.9 (4)
O(2)—C(8)—O(1)—C(9)	−178.6 (3)	C(7)—C(10)—C(11)—C(16)	−159.8 (3)
O(2)—C(8)—C(7)—C(6)	−1.6 (5)	C(8)—O(1)—C(9)—C(10)	0.1 (3)
O(2)—C(8)—C(7)—C(10)	177.6 (4)	C(8)—C(7)—C(10)—C(9)	2.1 (3)
O(3)—S(1)—C(14)—C(13)	38.5 (2)	C(8)—C(7)—C(10)—C(11)	−172.3 (3)
O(3)—S(1)—C(14)—C(15)	−141.1 (2)	C(9)—C(10)—C(11)—C(12)	−148.0 (3)
O(4)—S(1)—C(14)—C(13)	168.1 (2)	C(9)—C(10)—C(11)—C(16)	26.4 (4)
O(4)—S(1)—C(14)—C(15)	−11.5 (3)	C(10)—C(11)—C(12)—C(13)	173.0 (2)
C(1)—C(2)—C(3)—C(4)	0.8 (7)	C(10)—C(11)—C(16)—C(15)	−173.3 (2)
C(1)—C(6)—C(5)—C(4)	−0.1 (5)	C(11)—C(12)—C(13)—C(14)	0.4 (4)
C(1)—C(6)—C(7)—C(8)	55.8 (4)	C(11)—C(16)—C(15)—C(14)	0.3 (4)
C(1)—C(6)—C(7)—C(10)	−123.2 (4)	C(12)—C(11)—C(16)—C(15)	1.1 (4)
C(2)—C(1)—C(6)—C(5)	0.0 (5)	C(12)—C(13)—C(14)—C(15)	0.9 (4)
C(2)—C(1)—C(6)—C(7)	178.6 (4)	C(13)—C(12)—C(11)—C(16)	−1.4 (4)
C(2)—C(3)—C(4)—C(5)	−0.9 (6)	C(13)—C(14)—S(1)—C(17)	−76.2 (2)
C(3)—C(2)—C(1)—C(6)	−0.3 (7)	C(13)—C(14)—C(15)—C(16)	−1.3 (4)
C(3)—C(4)—C(5)—C(6)	0.5 (5)	C(15)—C(14)—S(1)—C(17)	104.2 (3)
C(4)—C(5)—C(6)—C(7)	−178.7 (3)

Symmetry codes: (i) x, y+1, z; (ii) −y, −x+1, −z+3/2; (iii) y+1/2, −x+1/2, z−1/4; (iv) −x+3/2, y+1/2, −z+5/4; (v) −y+1/2, x−1/2, z+1/4; (vi) −y+1/2, x−3/2, z+1/4; (vii) x+1/2, −y−1/2, −z+7/4; (viii) −y, −x, −z+3/2; (ix) x−1/2, −y−1/2, −z+7/4; (x) −y+1, −x+1, −z+3/2; (xi) y+3/2, −x+1/2, z−1/4.