Benzene­sulfonyl(1-hydroxy-1,2-di­hydro­naphthalen-2-yl)­aceto­nitrile

The regiochemistry and relative stereochemistry of the title compound, C₁₈H₁₅NO₃S, have been established. Molecules form centrosymmetric hydrogen-bonded pairs via intermolec­ular O—H...O hydrogen bonds [H...O 2.01 (3) Å and O—H...O 168 (3)°].

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.129
• Data-to-parameter ratio = 12.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PARST (Nardelli, 1995).

Benzenesulfonyl(1-hydroxy-1,2-dihydronaphthalen-2-yl)acetonitrile

Crystal data

C18H15NO3S	F(000) = 1360
Mr = 325.37	Dx = 1.379 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2933 reflections
a = 10.6135 (6) Å	θ = 2.6–25.0°
b = 12.6606 (8) Å	µ = 0.22 mm^−1
c = 23.3280 (16) Å	T = 150 K
V = 3134.7 (3) Å^3	Block, colourless
Z = 8	0.20 × 0.20 × 0.18 mm

Data collection

Nonius Kappa-CCD diffractometer	2278 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.052
Graphite monochromator	θmax = 25.0°, θmin = 2.6°
Detector resolution: 9 pixels mm^-1	h = −12→12
φ scans, and ω scans with κ offsets	k = −15→15
10898 measured reflections	l = −27→27
2753 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.129	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 2.8166P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
2753 reflections	Δρmax = 0.55 e Å^−3
213 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0112 (17)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.18980 (6)	0.61351 (5)	0.42170 (3)	0.0338 (2)
O1	0.05955 (16)	0.64097 (14)	0.60471 (8)	0.0355 (4)
H1O	0.010 (3)	0.594 (3)	0.5957 (14)	0.057 (10)*
O2	0.08634 (16)	0.53999 (14)	0.41808 (8)	0.0407 (5)
O3	0.31448 (16)	0.58027 (16)	0.40580 (8)	0.0424 (5)
N1	0.3810 (2)	0.78784 (19)	0.50919 (10)	0.0440 (6)
C1	0.1819 (2)	0.5958 (2)	0.59896 (11)	0.0321 (6)
H1	0.2440	0.6531	0.6073	0.039*
C2	0.2065 (2)	0.55895 (19)	0.53719 (11)	0.0326 (6)
H2	0.1394	0.5069	0.5268	0.039*
C3	0.3324 (2)	0.5031 (2)	0.53301 (12)	0.0395 (6)
H3	0.3805	0.5086	0.4988	0.047*
C4	0.3764 (2)	0.4467 (2)	0.57659 (12)	0.0411 (6)
H4	0.4547	0.4111	0.5725	0.049*
C5	0.3078 (2)	0.4379 (2)	0.63077 (12)	0.0370 (6)
C6	0.3379 (3)	0.3607 (2)	0.67128 (13)	0.0449 (7)
H6	0.4066	0.3143	0.6646	0.054*
C7	0.2680 (3)	0.3514 (2)	0.72130 (13)	0.0484 (7)
H7	0.2886	0.2983	0.7485	0.058*
C8	0.1687 (3)	0.4192 (2)	0.73167 (12)	0.0459 (7)
H8	0.1205	0.4122	0.7658	0.055*
C9	0.1393 (3)	0.4975 (2)	0.69220 (11)	0.0399 (6)
H9	0.0720	0.5449	0.7000	0.048*
C10	0.2066 (2)	0.5075 (2)	0.64171 (11)	0.0340 (6)
C11	0.1941 (2)	0.65445 (19)	0.49629 (11)	0.0316 (6)
H11	0.1131	0.6914	0.5052	0.038*
C12	0.2979 (2)	0.7310 (2)	0.50343 (11)	0.0343 (6)
C13	0.1527 (2)	0.7264 (2)	0.38145 (10)	0.0343 (6)
C14	0.2520 (3)	0.7919 (2)	0.36433 (11)	0.0409 (6)
H14	0.3362	0.7771	0.3757	0.049*
C15	0.2250 (3)	0.8782 (2)	0.33065 (12)	0.0459 (7)
H15	0.2911	0.9238	0.3187	0.055*
C16	0.1023 (3)	0.8992 (2)	0.31412 (12)	0.0481 (7)
H16	0.0848	0.9595	0.2912	0.058*
C17	0.0049 (3)	0.8330 (2)	0.33062 (12)	0.0447 (7)
H17	−0.0787	0.8475	0.3184	0.054*
C18	0.0288 (2)	0.7458 (2)	0.36484 (11)	0.0387 (6)
H18	−0.0376	0.7005	0.3767	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0281 (4)	0.0325 (4)	0.0409 (4)	−0.0012 (3)	−0.0016 (2)	−0.0044 (3)
O1	0.0258 (9)	0.0317 (10)	0.0488 (11)	0.0007 (8)	0.0014 (7)	−0.0048 (8)
O2	0.0349 (10)	0.0341 (10)	0.0531 (11)	−0.0087 (8)	−0.0065 (8)	−0.0038 (8)
O3	0.0289 (9)	0.0480 (11)	0.0505 (11)	0.0066 (8)	0.0009 (8)	−0.0085 (9)
N1	0.0391 (13)	0.0465 (14)	0.0464 (14)	−0.0080 (12)	−0.0034 (10)	−0.0001 (10)
C1	0.0224 (12)	0.0312 (13)	0.0428 (14)	−0.0019 (10)	−0.0003 (10)	−0.0013 (10)
C2	0.0259 (12)	0.0297 (13)	0.0422 (14)	−0.0001 (10)	0.0010 (10)	0.0000 (11)
C3	0.0268 (12)	0.0410 (15)	0.0507 (16)	0.0036 (11)	0.0067 (11)	0.0054 (12)
C4	0.0302 (13)	0.0369 (14)	0.0563 (17)	0.0050 (11)	0.0040 (11)	0.0027 (12)
C5	0.0325 (13)	0.0310 (14)	0.0476 (16)	−0.0004 (11)	−0.0025 (11)	0.0006 (11)
C6	0.0470 (16)	0.0341 (15)	0.0536 (18)	0.0033 (12)	−0.0060 (13)	0.0009 (12)
C7	0.0612 (19)	0.0378 (15)	0.0462 (16)	−0.0003 (14)	−0.0073 (14)	0.0073 (12)
C8	0.0510 (17)	0.0451 (16)	0.0417 (16)	−0.0081 (14)	0.0001 (12)	0.0008 (12)
C9	0.0384 (14)	0.0402 (15)	0.0413 (15)	−0.0034 (12)	0.0000 (11)	−0.0019 (12)
C10	0.0296 (12)	0.0306 (13)	0.0417 (15)	−0.0045 (10)	−0.0043 (10)	−0.0029 (11)
C11	0.0236 (12)	0.0317 (13)	0.0397 (14)	−0.0015 (10)	−0.0002 (9)	−0.0022 (10)
C12	0.0312 (13)	0.0340 (14)	0.0376 (14)	−0.0005 (11)	−0.0012 (10)	−0.0007 (11)
C13	0.0346 (13)	0.0347 (14)	0.0337 (13)	−0.0016 (11)	−0.0010 (10)	−0.0052 (10)
C14	0.0393 (14)	0.0409 (15)	0.0425 (15)	−0.0076 (12)	−0.0009 (12)	−0.0050 (12)
C15	0.0568 (18)	0.0389 (15)	0.0421 (16)	−0.0151 (14)	−0.0019 (13)	−0.0012 (12)
C16	0.066 (2)	0.0361 (15)	0.0419 (16)	−0.0010 (14)	−0.0031 (14)	0.0000 (12)
C17	0.0445 (16)	0.0462 (16)	0.0434 (15)	0.0083 (14)	−0.0020 (12)	−0.0016 (12)
C18	0.0347 (13)	0.0422 (15)	0.0390 (14)	−0.0002 (12)	0.0021 (11)	−0.0029 (11)

Geometric parameters (Å, º)

S1—O3	1.4373 (18)	C6—H6	0.95
S1—O2	1.4421 (18)	C7—C8	1.380 (4)
S1—C13	1.755 (3)	C7—H7	0.95
S1—C11	1.816 (3)	C8—C9	1.389 (4)
O1—C1	1.425 (3)	C8—H8	0.95
O1—H1O	0.82 (3)	C9—C10	1.383 (4)
N1—C12	1.146 (3)	C9—H9	0.95
C1—C10	1.521 (4)	C11—C12	1.476 (3)
C1—C2	1.537 (4)	C11—H11	1.00
C1—H1	1.00	C13—C18	1.393 (4)
C2—C3	1.516 (3)	C13—C14	1.399 (4)
C2—C11	1.546 (3)	C14—C15	1.376 (4)
C2—H2	1.00	C14—H14	0.95
C3—C4	1.327 (4)	C15—C16	1.384 (4)
C3—H3	0.95	C15—H15	0.95
C4—C5	1.463 (4)	C16—C17	1.385 (4)
C4—H4	0.95	C16—H16	0.95
C5—C6	1.396 (4)	C17—C18	1.386 (4)
C5—C10	1.413 (3)	C17—H17	0.95
C6—C7	1.387 (4)	C18—H18	0.95
O3—S1—O2	119.80 (11)	C7—C8—C9	119.9 (3)
O3—S1—C13	107.86 (12)	C7—C8—H8	120.0
O2—S1—C13	108.89 (11)	C9—C8—H8	120.0
O3—S1—C11	107.93 (11)	C10—C9—C8	120.9 (3)
O2—S1—C11	105.04 (11)	C10—C9—H9	119.5
C13—S1—C11	106.61 (12)	C8—C9—H9	119.5
C1—O1—H1O	106 (2)	C9—C10—C5	119.3 (2)
O1—C1—C10	113.0 (2)	C9—C10—C1	122.4 (2)
O1—C1—C2	111.40 (19)	C5—C10—C1	118.1 (2)
C10—C1—C2	111.3 (2)	C12—C11—C2	112.3 (2)
O1—C1—H1	106.9	C12—C11—S1	108.30 (17)
C10—C1—H1	106.9	C2—C11—S1	111.73 (17)
C2—C1—H1	106.9	C12—C11—H11	108.1
C3—C2—C1	110.6 (2)	C2—C11—H11	108.1
C3—C2—C11	113.6 (2)	S1—C11—H11	108.1
C1—C2—C11	109.1 (2)	N1—C12—C11	177.9 (3)
C3—C2—H2	107.8	C18—C13—C14	121.8 (3)
C1—C2—H2	107.8	C18—C13—S1	120.3 (2)
C11—C2—H2	107.8	C14—C13—S1	117.8 (2)
C4—C3—C2	120.8 (2)	C15—C14—C13	118.5 (3)
C4—C3—H3	119.6	C15—C14—H14	120.8
C2—C3—H3	119.6	C13—C14—H14	120.8
C3—C4—C5	121.9 (2)	C14—C15—C16	120.5 (3)
C3—C4—H4	119.1	C14—C15—H15	119.8
C5—C4—H4	119.1	C16—C15—H15	119.8
C6—C5—C10	119.2 (3)	C15—C16—C17	120.6 (3)
C6—C5—C4	121.7 (2)	C15—C16—H16	119.7
C10—C5—C4	119.1 (2)	C17—C16—H16	119.7
C7—C6—C5	120.4 (3)	C16—C17—C18	120.3 (3)
C7—C6—H6	119.8	C16—C17—H17	119.8
C5—C6—H6	119.8	C18—C17—H17	119.8
C8—C7—C6	120.2 (3)	C17—C18—C13	118.3 (3)
C8—C7—H7	119.9	C17—C18—H18	120.9
C6—C7—H7	119.9	C13—C18—H18	120.9
O1—C1—C2—C3	−175.4 (2)	C3—C2—C11—C12	−54.1 (3)
C10—C1—C2—C3	−48.3 (3)	C1—C2—C11—C12	69.8 (2)
O1—C1—C2—C11	59.0 (2)	C3—C2—C11—S1	67.9 (2)
C10—C1—C2—C11	−173.90 (19)	C1—C2—C11—S1	−168.28 (15)
C1—C2—C3—C4	32.9 (3)	O3—S1—C11—C12	51.5 (2)
C11—C2—C3—C4	155.9 (2)	O2—S1—C11—C12	−179.62 (16)
C2—C3—C4—C5	−1.5 (4)	C13—S1—C11—C12	−64.16 (19)
C3—C4—C5—C6	165.0 (3)	O3—S1—C11—C2	−72.76 (18)
C3—C4—C5—C10	−13.4 (4)	O2—S1—C11—C2	56.12 (18)
C10—C5—C6—C7	1.0 (4)	C13—S1—C11—C2	171.59 (16)
C4—C5—C6—C7	−177.4 (3)	O3—S1—C13—C18	147.7 (2)
C5—C6—C7—C8	−0.6 (4)	O2—S1—C13—C18	16.2 (2)
C6—C7—C8—C9	−0.6 (4)	C11—S1—C13—C18	−96.6 (2)
C7—C8—C9—C10	1.4 (4)	O3—S1—C13—C14	−28.9 (2)
C8—C9—C10—C5	−1.0 (4)	O2—S1—C13—C14	−160.38 (19)
C8—C9—C10—C1	−176.6 (2)	C11—S1—C13—C14	86.8 (2)
C6—C5—C10—C9	−0.2 (4)	C18—C13—C14—C15	0.7 (4)
C4—C5—C10—C9	178.3 (2)	S1—C13—C14—C15	177.2 (2)
C6—C5—C10—C1	175.6 (2)	C13—C14—C15—C16	−0.2 (4)
C4—C5—C10—C1	−5.9 (3)	C14—C15—C16—C17	−0.7 (4)
O1—C1—C10—C9	−21.4 (3)	C15—C16—C17—C18	1.2 (4)
C2—C1—C10—C9	−147.6 (2)	C16—C17—C18—C13	−0.6 (4)
O1—C1—C10—C5	162.9 (2)	C14—C13—C18—C17	−0.3 (4)
C2—C1—C10—C5	36.7 (3)	S1—C13—C18—C17	−176.74 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	0.82 (3)	2.01 (3)	2.816 (3)	168 (3)

Symmetry code: (i) −x, −y+1, −z+1.