(1E)-6-Meth-oxy-3,4-dihydro-naphthalen-1(2H)-one O-(p-tolyl-sulfon-yl)oxime.

In the title compound, C(18)H(19)NO(4)S, the two benzene rings form a dihedral angle of 68.37 (11)°. One of the C atoms of the fused ring bonded to the N atom displays positional disorder with site-occupation factors of 0.763 (7) and 0.237 (7) and the ring has an envelope conformation with the disordered C atoms located on opposite sides of the plane formed by the other atoms. In the crystal, inter-molecular C-H⋯O hydrogen bonds link the mol-ecules to form a two-dimensional supra-molecular network. The crystal structure is further stablized by weak inter-molecular C-H⋯π inter-actions.

Related literature

The title compound has been used in our study (Byoung et al. 2000 ▶) of the effect of the reaction conditions on the Beckmanm rearrangement of 6-meth­oxy-3,4-dihydro­naphthalen-1(2H)-one oxime (Xiao et al., 2007 ▶). For details of the synthesis, see Byoung et al. (2000 ▶). For a related structure, see Jin et al. (2010 ▶).

Experimental

Crystal data

C18H19NO4S

M = 345.41

Monoclinic,

a = 13.478 (5) Å

b = 9.255 (5) Å

c = 17.707 (8) Å

β = 128.22 (3)°

V = 1735.3 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 290 K

0.12 × 0.11 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.976, T max = 0.980

16447 measured reflections

3939 independent reflections

3052 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.135

S = 1.01

3939 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.34 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Molecular Structure Corporation & Rigaku, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810039899/vm2048sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039899/vm2048Isup2.hkl

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

C18H19NO4S	F(000) = 728
Mr = 345.41	Dx = 1.322 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 11474 reflections
a = 13.478 (5) Å	θ = 3.1–27.5°
b = 9.255 (5) Å	µ = 0.21 mm−1
c = 17.707 (8) Å	T = 290 K
β = 128.22 (3)°	Block, colorless
V = 1735.3 (16) Å3	0.12 × 0.11 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	3939 independent reflections
Radiation source: fine-focus sealed tube	3052 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −17→17
Tmin = 0.976, Tmax = 0.980	k = −11→11
16447 measured reflections	l = −22→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0686P)2 + 0.4858P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3939 reflections	Δρmax = 0.44 e Å−3
230 parameters	Δρmin = −0.34 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.069 (4)

Experimental. (See detailed section in the paper)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	1.21154 (4)	1.01704 (6)	0.84699 (3)	0.05339 (18)
O1	1.32298 (13)	1.09992 (16)	0.88664 (11)	0.0688 (4)
O2	1.11691 (15)	1.01052 (18)	0.74596 (10)	0.0720 (4)
O3	1.15381 (12)	1.09228 (14)	0.89346 (9)	0.0557 (3)
O4	0.53547 (14)	0.81979 (17)	0.77887 (12)	0.0738 (4)
N1	1.03738 (14)	1.01680 (16)	0.85957 (11)	0.0510 (4)
C1	1.3561 (3)	0.4210 (3)	1.0232 (2)	0.0928 (8)
H1A	1.3260	0.3480	0.9750	0.139*
H1B	1.3191	0.4067	1.0547	0.139*
H1C	1.4464	0.4148	1.0696	0.139*
C2	1.31973 (19)	0.5680 (2)	0.97663 (15)	0.0600 (5)
C3	1.19864 (19)	0.5964 (2)	0.89321 (15)	0.0624 (5)
H3	1.1395	0.5222	0.8642	0.075*
C4	1.16441 (17)	0.7318 (2)	0.85263 (13)	0.0562 (5)
H4	1.0827	0.7489	0.7971	0.067*
C5	1.25256 (15)	0.8425 (2)	0.89508 (12)	0.0475 (4)
C6	1.37496 (16)	0.8166 (2)	0.97757 (13)	0.0534 (4)
H6	1.4345	0.8905	1.0058	0.064*
C7	1.40688 (18)	0.6800 (2)	1.01695 (14)	0.0613 (5)
H7	1.4889	0.6625	1.0719	0.074*
C8	0.97831 (16)	1.08889 (18)	0.88218 (11)	0.0450 (4)
C9	1.0207 (2)	1.2307 (2)	0.93435 (15)	0.0603 (5)
H9A	1.0587	1.2886	0.9126	0.072*
H9B	1.0842	1.2136	1.0027	0.072*
C10	0.9081 (4)	1.3146 (3)	0.9165 (3)	0.0698 (12)	0.763 (7)
H10A	0.9403	1.3983	0.9584	0.084*	0.763 (7)
H10B	0.8536	1.3488	0.8506	0.084*	0.763 (7)
C11	0.8345 (3)	1.2276 (3)	0.9335 (2)	0.0809 (7)
H11A	0.7615	1.2826	0.9155	0.097*
H11B	0.8851	1.2063	1.0017	0.097*
C12	0.79064 (18)	1.08776 (19)	0.87810 (13)	0.0529 (4)
C10'	0.9604 (8)	1.2634 (9)	0.9825 (7)	0.053 (3)	0.237 (7)
H10C	1.0092	1.2141	1.0441	0.064*	0.237 (7)
H10D	0.9688	1.3662	0.9958	0.064*	0.237 (7)
C13	0.86031 (17)	1.02224 (18)	0.85398 (12)	0.0454 (4)
C14	0.81694 (19)	0.8901 (2)	0.80425 (15)	0.0574 (5)
H14	0.8619	0.8455	0.7868	0.069*
C15	0.70982 (19)	0.8259 (2)	0.78110 (14)	0.0593 (5)
H15	0.6834	0.7377	0.7491	0.071*
C16	0.64081 (18)	0.8922 (2)	0.80522 (14)	0.0549 (5)
C17	0.6813 (2)	1.0222 (2)	0.85367 (16)	0.0616 (5)
H17	0.6352	1.0664	0.8702	0.074*
C18	0.4673 (3)	0.8776 (3)	0.8090 (2)	0.0938 (8)
H18A	0.4301	0.9682	0.7773	0.141*
H18B	0.5238	0.8923	0.8773	0.141*
H18C	0.4020	0.8112	0.7928	0.141*

	U11	U22	U33	U12	U13	U23
S1	0.0438 (3)	0.0658 (3)	0.0536 (3)	−0.0040 (2)	0.0316 (2)	0.0018 (2)
O1	0.0533 (8)	0.0715 (9)	0.0878 (10)	−0.0104 (7)	0.0468 (8)	0.0057 (7)
O2	0.0609 (9)	0.0995 (12)	0.0511 (8)	0.0048 (8)	0.0324 (7)	0.0083 (7)
O3	0.0463 (7)	0.0579 (8)	0.0656 (8)	−0.0083 (6)	0.0360 (6)	−0.0078 (6)
O4	0.0601 (9)	0.0825 (10)	0.0925 (11)	−0.0191 (8)	0.0540 (8)	−0.0229 (8)
N1	0.0445 (8)	0.0534 (8)	0.0581 (9)	−0.0071 (6)	0.0333 (7)	−0.0044 (7)
C1	0.0898 (18)	0.0653 (15)	0.120 (2)	0.0104 (13)	0.0630 (17)	0.0081 (14)
C2	0.0582 (11)	0.0550 (11)	0.0729 (12)	−0.0001 (9)	0.0437 (10)	−0.0079 (9)
C3	0.0536 (11)	0.0591 (12)	0.0713 (12)	−0.0154 (9)	0.0371 (10)	−0.0208 (9)
C4	0.0404 (9)	0.0651 (12)	0.0523 (10)	−0.0100 (8)	0.0234 (8)	−0.0147 (8)
C5	0.0384 (8)	0.0581 (10)	0.0473 (9)	−0.0061 (7)	0.0271 (7)	−0.0084 (7)
C6	0.0372 (9)	0.0621 (11)	0.0547 (10)	−0.0100 (8)	0.0253 (8)	−0.0095 (8)
C7	0.0413 (10)	0.0717 (13)	0.0605 (11)	0.0022 (9)	0.0263 (9)	−0.0019 (9)
C8	0.0485 (9)	0.0461 (9)	0.0425 (8)	0.0004 (7)	0.0292 (7)	0.0029 (7)
C9	0.0692 (12)	0.0513 (10)	0.0713 (12)	−0.0148 (9)	0.0490 (11)	−0.0123 (9)
C10	0.093 (2)	0.0427 (15)	0.097 (3)	−0.0078 (15)	0.070 (2)	−0.0106 (16)
C11	0.0880 (17)	0.0619 (13)	0.1167 (19)	−0.0127 (12)	0.0753 (16)	−0.0318 (13)
C12	0.0575 (11)	0.0479 (10)	0.0607 (10)	−0.0007 (8)	0.0404 (9)	−0.0056 (8)
C10'	0.059 (5)	0.041 (4)	0.055 (5)	−0.001 (3)	0.033 (4)	−0.005 (4)
C13	0.0498 (9)	0.0462 (9)	0.0452 (8)	−0.0020 (7)	0.0318 (8)	−0.0022 (7)
C14	0.0605 (11)	0.0594 (11)	0.0698 (12)	−0.0097 (9)	0.0490 (10)	−0.0185 (9)
C15	0.0619 (12)	0.0582 (11)	0.0661 (11)	−0.0140 (9)	0.0438 (10)	−0.0210 (9)
C16	0.0505 (10)	0.0610 (11)	0.0583 (10)	−0.0078 (8)	0.0362 (9)	−0.0062 (8)
C17	0.0608 (12)	0.0628 (12)	0.0780 (13)	−0.0003 (9)	0.0513 (11)	−0.0110 (10)
C18	0.0728 (16)	0.0988 (19)	0.140 (2)	−0.0144 (14)	0.0808 (18)	−0.0213 (17)

S1—O2	1.4169 (17)	C9—C10	1.553 (4)
S1—O1	1.4257 (15)	C9—H9A	0.9700
S1—O3	1.5997 (14)	C9—H9B	0.9700
S1—C5	1.748 (2)	C10—C11	1.446 (4)
O3—N1	1.465 (2)	C10—H10A	0.9700
O4—C16	1.365 (2)	C10—H10B	0.9700
O4—C18	1.422 (3)	C10—H10D	1.2028
N1—C8	1.278 (2)	C11—C12	1.507 (3)
C1—C2	1.507 (3)	C11—H11A	0.9700
C1—H1A	0.9600	C11—H11B	0.9700
C1—H1B	0.9600	C12—C13	1.388 (2)
C1—H1C	0.9600	C12—C17	1.393 (3)
C2—C7	1.388 (3)	C10'—H10C	0.9700
C2—C3	1.390 (3)	C10'—H10D	0.9700
C3—C4	1.374 (3)	C13—C14	1.406 (3)
C3—H3	0.9300	C14—C15	1.368 (3)
C4—C5	1.387 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.384 (3)
C5—C6	1.390 (3)	C15—H15	0.9300
C6—C7	1.378 (3)	C16—C17	1.379 (3)
C6—H6	0.9300	C17—H17	0.9300
C7—H7	0.9300	C18—H18A	0.9600
C8—C13	1.475 (2)	C18—H18B	0.9600
C8—C9	1.499 (3)	C18—H18C	0.9600
O2—S1—O1	119.72 (10)	C11—C10—C9	112.9 (3)
O2—S1—O3	108.89 (9)	C11—C10—H10A	109.0
O1—S1—O3	102.24 (9)	C9—C10—H10A	109.0
O2—S1—C5	110.00 (9)	C11—C10—H10B	109.0
O1—S1—C5	109.74 (9)	C9—C10—H10B	109.0
O3—S1—C5	105.04 (8)	H10A—C10—H10B	107.8
N1—O3—S1	108.69 (10)	C11—C10—H10D	92.1
C16—O4—C18	117.66 (18)	C9—C10—H10D	95.1
C8—N1—O3	109.86 (14)	H10A—C10—H10D	29.6
C2—C1—H1A	109.5	H10B—C10—H10D	137.4
C2—C1—H1B	109.5	C10—C11—C12	112.7 (2)
H1A—C1—H1B	109.5	C10—C11—H11A	109.1
C2—C1—H1C	109.5	C12—C11—H11A	109.1
H1A—C1—H1C	109.5	C10—C11—H11B	109.1
H1B—C1—H1C	109.5	C12—C11—H11B	109.1
C7—C2—C3	117.94 (19)	H11A—C11—H11B	107.8
C7—C2—C1	120.5 (2)	C13—C12—C17	120.08 (17)
C3—C2—C1	121.5 (2)	C13—C12—C11	120.54 (18)
C4—C3—C2	121.47 (18)	C17—C12—C11	119.35 (18)
C4—C3—H3	119.3	H10C—C10'—H10D	107.1
C2—C3—H3	119.3	C12—C13—C14	118.31 (17)
C3—C4—C5	119.52 (18)	C12—C13—C8	120.39 (16)
C3—C4—H4	120.2	C14—C13—C8	121.28 (16)
C5—C4—H4	120.2	C15—C14—C13	121.21 (17)
C4—C5—C6	120.27 (18)	C15—C14—H14	119.4
C4—C5—S1	120.82 (14)	C13—C14—H14	119.4
C6—C5—S1	118.91 (14)	C14—C15—C16	120.07 (18)
C7—C6—C5	119.09 (17)	C14—C15—H15	120.0
C7—C6—H6	120.5	C16—C15—H15	120.0
C5—C6—H6	120.5	O4—C16—C17	124.63 (18)
C6—C7—C2	121.69 (18)	O4—C16—C15	115.63 (17)
C6—C7—H7	119.2	C17—C16—C15	119.73 (18)
C2—C7—H7	119.2	C16—C17—C12	120.59 (18)
N1—C8—C13	115.19 (16)	C16—C17—H17	119.7
N1—C8—C9	125.19 (17)	C12—C17—H17	119.7
C13—C8—C9	119.62 (15)	O4—C18—H18A	109.5
C8—C9—C10	111.14 (19)	O4—C18—H18B	109.5
C8—C9—H9A	109.4	H18A—C18—H18B	109.5
C10—C9—H9A	109.4	O4—C18—H18C	109.5
C8—C9—H9B	109.4	H18A—C18—H18C	109.5
C10—C9—H9B	109.4	H18B—C18—H18C	109.5
H9A—C9—H9B	108.0
O2—S1—O3—N1	52.91 (14)	C8—C9—C10—C11	50.4 (4)
O1—S1—O3—N1	−179.47 (11)	C9—C10—C11—C12	−53.4 (4)
C5—S1—O3—N1	−64.88 (12)	C10—C11—C12—C13	28.5 (4)
S1—O3—N1—C8	−169.09 (12)	C10—C11—C12—C17	−153.5 (3)
C7—C2—C3—C4	−1.6 (3)	C17—C12—C13—C14	0.5 (3)
C1—C2—C3—C4	177.8 (2)	C11—C12—C13—C14	178.5 (2)
C2—C3—C4—C5	0.6 (3)	C17—C12—C13—C8	−178.15 (17)
C3—C4—C5—C6	0.6 (3)	C11—C12—C13—C8	−0.1 (3)
C3—C4—C5—S1	−178.62 (15)	N1—C8—C13—C12	177.43 (16)
O2—S1—C5—C4	−31.08 (18)	C9—C8—C13—C12	−2.0 (3)
O1—S1—C5—C4	−164.80 (15)	N1—C8—C13—C14	−1.1 (3)
O3—S1—C5—C4	85.95 (16)	C9—C8—C13—C14	179.43 (18)
O2—S1—C5—C6	149.71 (15)	C12—C13—C14—C15	−0.9 (3)
O1—S1—C5—C6	16.00 (17)	C8—C13—C14—C15	177.70 (18)
O3—S1—C5—C6	−93.26 (16)	C13—C14—C15—C16	1.1 (3)
C4—C5—C6—C7	−0.7 (3)	C18—O4—C16—C17	−4.3 (3)
S1—C5—C6—C7	178.53 (15)	C18—O4—C16—C15	174.9 (2)
C5—C6—C7—C2	−0.4 (3)	C14—C15—C16—O4	179.88 (18)
C3—C2—C7—C6	1.5 (3)	C14—C15—C16—C17	−0.8 (3)
C1—C2—C7—C6	−177.9 (2)	O4—C16—C17—C12	179.6 (2)
O3—N1—C8—C13	−178.59 (13)	C15—C16—C17—C12	0.4 (3)
O3—N1—C8—C9	0.8 (2)	C13—C12—C17—C16	−0.2 (3)
N1—C8—C9—C10	158.5 (2)	C11—C12—C17—C16	−178.3 (2)
C13—C8—C9—C10	−22.2 (3)

Cg1 is the centroid of the C12–C17 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.57	3.293 (3)	135
C10—H10B···O2ii	0.97	2.48	3.237 (5)	135
C15—H15···O1iii	0.93	2.68	3.430 (3)	139
C9—H9B···Cg1iv	0.97	2.85	3.750 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C12–C17 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.57	3.293 (3)	135
C10—H10B⋯O2ii	0.97	2.48	3.237 (5)	135
C15—H15⋯O1iii	0.93	2.68	3.430 (3)	139
C9—H9B⋯Cg1iv	0.97	2.85	3.750 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .