Methyl 2,2'-dimethyl-4'-[2-(methyl-sulfan-yl)eth-yl]-1,3-dioxo-2,3-dihydro-1H,4'H-spiro-[isoquinoline-4,5'-oxazole]-4'-carboxyl-ate.

In the isoquinoline ring system of the title mol-ecule, C(18)H(20)N(2)O(5)S, the fused N-heterocyclic ring is distorted towards a half-boat conformation. The methyl formate moiety is disordered over two sets of sites with refined occupancies of 0.882 (5) and 0.118 (5). In the crystal, mol-ecules are linked via weak inter-molecular C-H⋯O hydrogen bonds into one-dimensional chains along [010].

Related literature

For general background to and the biological activity of isoquinoline- and oxazole-containing compounds, see: Yu et al. (2010 ▶); Huang et al. (2011 ▶); Harris et al. (2005 ▶); Vintonyak et al. (2010 ▶); Badillo et al. (2010 ▶, 2011 ▶); Wang et al. (2010 ▶); Nair et al. (2002 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For related structures, see: Fun et al. (2011a ▶,b ▶,c ▶,d ▶).

Experimental

Crystal data

C18H20N2O5S

M = 376.42

Monoclinic,

a = 15.0052 (15) Å

b = 8.4548 (8) Å

c = 15.4915 (15) Å

β = 114.621 (2)°

V = 1786.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 100 K

0.18 × 0.17 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.971

14571 measured reflections

4063 independent reflections

3343 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.120

S = 1.03

4063 reflections

251 parameters

5 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811030133/lh5290sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030133/lh5290Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030133/lh5290Isup3.cml

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

C18H20N2O5S	F(000) = 792
Mr = 376.42	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4051 reflections
a = 15.0052 (15) Å	θ = 2.8–32.2°
b = 8.4548 (8) Å	µ = 0.21 mm−1
c = 15.4915 (15) Å	T = 100 K
β = 114.621 (2)°	Block, colourless
V = 1786.7 (3) Å3	0.18 × 0.17 × 0.14 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4063 independent reflections
Radiation source: fine-focus sealed tube	3343 reflections with I > 2σ(I)
graphite	Rint = 0.046
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −19→19
Tmin = 0.963, Tmax = 0.971	k = −10→10
14571 measured reflections	l = −20→11

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0626P)2 + 0.5509P] where P = (Fo2 + 2Fc2)/3
4063 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.37 e Å−3
5 restraints	Δρmin = −0.32 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.27696 (3)	1.10762 (5)	0.32691 (3)	0.02485 (13)
O1	0.33441 (10)	0.50297 (14)	0.39092 (8)	0.0279 (3)
O2	0.46168 (9)	0.36107 (18)	0.18390 (11)	0.0383 (3)
O3	0.14782 (8)	0.46617 (13)	0.26111 (8)	0.0221 (3)
N1	0.39944 (10)	0.44834 (16)	0.28567 (10)	0.0217 (3)
N2	0.10538 (10)	0.70860 (16)	0.19482 (10)	0.0235 (3)
C1	0.32154 (12)	0.47773 (18)	0.30951 (11)	0.0194 (3)
C2	0.38950 (12)	0.38490 (19)	0.19925 (12)	0.0231 (3)
C3	0.28965 (11)	0.33921 (18)	0.13157 (11)	0.0185 (3)
C4	0.27876 (13)	0.24490 (19)	0.05343 (12)	0.0244 (4)
H4A	0.3335	0.2156	0.0435	0.029*
C5	0.18662 (14)	0.1955 (2)	−0.00886 (12)	0.0295 (4)
H5A	0.1792	0.1324	−0.0606	0.035*
C6	0.10523 (14)	0.2401 (2)	0.00594 (13)	0.0306 (4)
H6A	0.0433	0.2056	−0.0357	0.037*
C7	0.11511 (12)	0.3360 (2)	0.08231 (12)	0.0248 (4)
H7A	0.0599	0.3668	0.0910	0.030*
C8	0.20750 (11)	0.38568 (17)	0.14568 (11)	0.0168 (3)
C9	0.22153 (11)	0.49560 (18)	0.22694 (11)	0.0168 (3)
C10	0.08495 (13)	0.5926 (2)	0.23464 (13)	0.0257 (4)
C11	0.20146 (11)	0.67886 (18)	0.19522 (11)	0.0176 (3)
C12	0.27506 (12)	0.79601 (18)	0.26518 (11)	0.0201 (3)
H12A	0.2747	0.7840	0.3273	0.024*
H12B	0.3405	0.7719	0.2710	0.024*
C13	0.24935 (14)	0.96755 (19)	0.23154 (12)	0.0244 (4)
H13A	0.1799	0.9736	0.1903	0.029*
H13B	0.2851	0.9971	0.1944	0.029*
C14	0.40732 (16)	1.0840 (2)	0.38860 (16)	0.0436 (5)
H14A	0.4320	1.1541	0.4422	0.065*
H14B	0.4376	1.1086	0.3465	0.065*
H14C	0.4221	0.9767	0.4101	0.065*
O4A	0.2865 (2)	0.6950 (4)	0.0984 (2)	0.0223 (6)	0.882 (5)
O5A	0.1227 (3)	0.7245 (6)	0.0253 (2)	0.0350 (8)	0.882 (5)
C15A	0.19637 (16)	0.7028 (3)	0.09603 (17)	0.0182 (5)	0.882 (5)
C16A	0.29113 (18)	0.7026 (3)	0.00803 (15)	0.0350 (6)	0.882 (5)
H16A	0.3583	0.6962	0.0169	0.053*	0.882 (5)
H16B	0.2633	0.8007	−0.0225	0.053*	0.882 (5)
H16C	0.2549	0.6160	−0.0308	0.053*	0.882 (5)
O4B	0.1389 (17)	0.715 (4)	0.0255 (17)	0.018 (5)*	0.118 (5)
O5B	0.3045 (17)	0.707 (4)	0.114 (2)	0.028 (7)*	0.118 (5)
C15B	0.2218 (18)	0.697 (5)	0.104 (2)	0.045 (5)*	0.118 (5)
C16B	0.1512 (14)	0.732 (2)	−0.0598 (13)	0.045 (5)*	0.118 (5)
H16D	0.0883	0.7433	−0.1121	0.067*	0.118 (5)
H16E	0.1834	0.6394	−0.0695	0.067*	0.118 (5)
H16F	0.1905	0.8234	−0.0556	0.067*	0.118 (5)
C17	−0.00079 (17)	0.5767 (3)	0.2584 (2)	0.0491 (6)
H17A	−0.0411	0.6694	0.2377	0.074*
H17B	0.0215	0.5650	0.3258	0.074*
H17C	−0.0383	0.4853	0.2270	0.074*
C18	0.49909 (13)	0.4745 (2)	0.35923 (15)	0.0379 (5)
H18A	0.5443	0.4075	0.3472	0.057*
H18B	0.5008	0.4500	0.4204	0.057*
H18C	0.5172	0.5832	0.3581	0.057*

	U11	U22	U33	U12	U13	U23
S1	0.0334 (2)	0.0158 (2)	0.0250 (2)	0.00124 (15)	0.01191 (19)	−0.00212 (15)
O1	0.0415 (7)	0.0212 (6)	0.0162 (6)	0.0016 (5)	0.0073 (5)	−0.0005 (4)
O2	0.0252 (7)	0.0440 (8)	0.0519 (9)	−0.0037 (6)	0.0221 (7)	−0.0092 (7)
O3	0.0268 (6)	0.0174 (6)	0.0292 (6)	0.0042 (4)	0.0187 (5)	0.0061 (5)
N1	0.0173 (6)	0.0205 (7)	0.0218 (7)	−0.0020 (5)	0.0025 (6)	0.0003 (5)
N2	0.0232 (7)	0.0200 (7)	0.0289 (8)	0.0031 (5)	0.0125 (6)	0.0038 (6)
C1	0.0255 (8)	0.0123 (7)	0.0182 (8)	−0.0006 (6)	0.0070 (7)	0.0008 (6)
C2	0.0227 (8)	0.0197 (8)	0.0286 (9)	0.0000 (6)	0.0122 (7)	0.0012 (6)
C3	0.0226 (8)	0.0161 (7)	0.0172 (7)	0.0009 (6)	0.0088 (6)	0.0021 (6)
C4	0.0341 (9)	0.0205 (8)	0.0222 (8)	0.0049 (7)	0.0153 (7)	0.0009 (6)
C5	0.0424 (10)	0.0229 (9)	0.0185 (8)	0.0027 (7)	0.0080 (8)	−0.0040 (6)
C6	0.0290 (9)	0.0268 (9)	0.0242 (9)	−0.0017 (7)	−0.0009 (8)	−0.0044 (7)
C7	0.0204 (8)	0.0228 (8)	0.0265 (9)	0.0011 (6)	0.0052 (7)	−0.0005 (7)
C8	0.0197 (7)	0.0137 (7)	0.0159 (7)	0.0007 (5)	0.0064 (6)	0.0017 (5)
C9	0.0202 (7)	0.0145 (7)	0.0174 (7)	−0.0001 (5)	0.0095 (6)	0.0002 (5)
C10	0.0273 (9)	0.0205 (8)	0.0329 (9)	0.0050 (6)	0.0162 (8)	0.0025 (7)
C11	0.0229 (8)	0.0135 (7)	0.0167 (7)	0.0015 (6)	0.0085 (6)	0.0022 (6)
C12	0.0297 (8)	0.0148 (7)	0.0153 (7)	−0.0006 (6)	0.0087 (7)	−0.0001 (6)
C13	0.0356 (9)	0.0159 (8)	0.0193 (8)	−0.0006 (6)	0.0091 (7)	0.0009 (6)
C14	0.0371 (11)	0.0313 (10)	0.0445 (12)	0.0036 (8)	−0.0007 (10)	−0.0062 (9)
O4A	0.0278 (14)	0.0245 (10)	0.0164 (12)	−0.0063 (10)	0.0109 (10)	−0.0028 (9)
O5A	0.0325 (15)	0.0456 (15)	0.0204 (10)	0.0042 (14)	0.0045 (10)	0.0055 (7)
C15A	0.0253 (12)	0.0130 (9)	0.0157 (10)	−0.0023 (10)	0.0080 (10)	0.0001 (7)
C16A	0.0484 (14)	0.0411 (13)	0.0268 (11)	−0.0108 (10)	0.0269 (10)	−0.0040 (9)
C17	0.0464 (12)	0.0363 (11)	0.0867 (18)	0.0122 (9)	0.0496 (13)	0.0174 (11)
C18	0.0222 (9)	0.0357 (11)	0.0391 (11)	−0.0067 (7)	−0.0038 (8)	−0.0004 (9)

S1—C14	1.795 (2)	C11—C15B	1.57 (3)
S1—C13	1.8019 (17)	C12—C13	1.535 (2)
O1—C1	1.213 (2)	C12—H12A	0.9700
O2—C2	1.218 (2)	C12—H12B	0.9700
O3—C10	1.3706 (19)	C13—H13A	0.9700
O3—C9	1.4328 (18)	C13—H13B	0.9700
N1—C1	1.387 (2)	C14—H14A	0.9600
N1—C2	1.391 (2)	C14—H14B	0.9600
N1—C18	1.471 (2)	C14—H14C	0.9600
N2—C10	1.263 (2)	O4A—C15A	1.340 (3)
N2—C11	1.461 (2)	O4A—C16A	1.431 (4)
C1—C9	1.520 (2)	O5A—C15A	1.203 (4)
C2—C3	1.478 (2)	C16A—H16A	0.9600
C3—C8	1.395 (2)	C16A—H16B	0.9600
C3—C4	1.401 (2)	C16A—H16C	0.9600
C4—C5	1.380 (3)	O4B—C15B	1.336 (18)
C4—H4A	0.9300	O4B—C16B	1.416 (19)
C5—C6	1.386 (3)	O5B—C15B	1.189 (19)
C5—H5A	0.9300	C16B—H16D	0.9600
C6—C7	1.390 (3)	C16B—H16E	0.9600
C6—H6A	0.9300	C16B—H16F	0.9600
C7—C8	1.389 (2)	C17—H17A	0.9600
C7—H7A	0.9300	C17—H17B	0.9600
C8—C9	1.507 (2)	C17—H17C	0.9600
C9—C11	1.615 (2)	C18—H18A	0.9600
C10—C17	1.484 (3)	C18—H18B	0.9600
C11—C15A	1.520 (3)	C18—H18C	0.9600
C11—C12	1.542 (2)
C14—S1—C13	100.99 (9)	C13—C12—H12A	109.4
C10—O3—C9	107.16 (12)	C11—C12—H12A	109.4
C1—N1—C2	124.12 (13)	C13—C12—H12B	109.4
C1—N1—C18	117.65 (15)	C11—C12—H12B	109.4
C2—N1—C18	118.05 (15)	H12A—C12—H12B	108.0
C10—N2—C11	107.72 (13)	C12—C13—S1	113.78 (11)
O1—C1—N1	121.45 (15)	C12—C13—H13A	108.8
O1—C1—C9	122.08 (15)	S1—C13—H13A	108.8
N1—C1—C9	116.08 (13)	C12—C13—H13B	108.8
O2—C2—N1	120.26 (16)	S1—C13—H13B	108.8
O2—C2—C3	122.63 (16)	H13A—C13—H13B	107.7
N1—C2—C3	116.99 (14)	S1—C14—H14A	109.5
C8—C3—C4	120.20 (15)	S1—C14—H14B	109.5
C8—C3—C2	121.07 (14)	H14A—C14—H14B	109.5
C4—C3—C2	118.72 (14)	S1—C14—H14C	109.5
C5—C4—C3	119.91 (16)	H14A—C14—H14C	109.5
C5—C4—H4A	120.0	H14B—C14—H14C	109.5
C3—C4—H4A	120.0	C15A—O4A—C16A	115.5 (3)
C4—C5—C6	119.80 (16)	O5A—C15A—O4A	124.6 (3)
C4—C5—H5A	120.1	O5A—C15A—C11	125.5 (2)
C6—C5—H5A	120.1	O4A—C15A—C11	109.9 (2)
C5—C6—C7	120.72 (16)	O4A—C16A—H16A	109.5
C5—C6—H6A	119.6	O4A—C16A—H16B	109.5
C7—C6—H6A	119.6	H16A—C16A—H16B	109.5
C8—C7—C6	119.95 (16)	O4A—C16A—H16C	109.5
C8—C7—H7A	120.0	H16A—C16A—H16C	109.5
C6—C7—H7A	120.0	H16B—C16A—H16C	109.5
C7—C8—C3	119.41 (15)	C15B—O4B—C16B	115 (2)
C7—C8—C9	121.87 (14)	O5B—C15B—O4B	129 (3)
C3—C8—C9	118.65 (14)	O5B—C15B—C11	118 (2)
O3—C9—C8	109.92 (12)	O4B—C15B—C11	112 (2)
O3—C9—C1	108.37 (12)	O4B—C16B—H16D	109.5
C8—C9—C1	112.76 (12)	O4B—C16B—H16E	109.5
O3—C9—C11	101.78 (11)	H16D—C16B—H16E	109.5
C8—C9—C11	113.19 (12)	O4B—C16B—H16F	109.5
C1—C9—C11	110.17 (12)	H16D—C16B—H16F	109.5
N2—C10—O3	118.36 (15)	H16E—C16B—H16F	109.5
N2—C10—C17	127.13 (16)	C10—C17—H17A	109.5
O3—C10—C17	114.50 (15)	C10—C17—H17B	109.5
N2—C11—C15A	109.81 (14)	H17A—C17—H17B	109.5
N2—C11—C12	108.00 (13)	C10—C17—H17C	109.5
C15A—C11—C12	110.16 (15)	H17A—C17—H17C	109.5
N2—C11—C15B	122.6 (9)	H17B—C17—H17C	109.5
C12—C11—C15B	102.6 (12)	N1—C18—H18A	109.5
N2—C11—C9	103.00 (12)	N1—C18—H18B	109.5
C15A—C11—C9	111.08 (15)	H18A—C18—H18B	109.5
C12—C11—C9	114.46 (12)	N1—C18—H18C	109.5
C15B—C11—C9	106.7 (15)	H18A—C18—H18C	109.5
C13—C12—C11	111.29 (13)	H18B—C18—H18C	109.5
C2—N1—C1—O1	165.16 (15)	C10—N2—C11—C15A	129.83 (18)
C18—N1—C1—O1	−9.9 (2)	C10—N2—C11—C12	−110.02 (15)
C2—N1—C1—C9	−21.8 (2)	C10—N2—C11—C15B	131.3 (18)
C18—N1—C1—C9	163.11 (14)	C10—N2—C11—C9	11.44 (17)
C1—N1—C2—O2	−179.30 (16)	O3—C9—C11—N2	−13.71 (14)
C18—N1—C2—O2	−4.2 (2)	C8—C9—C11—N2	104.20 (14)
C1—N1—C2—C3	−3.2 (2)	C1—C9—C11—N2	−128.52 (13)
C18—N1—C2—C3	171.80 (15)	O3—C9—C11—C15A	−131.21 (14)
O2—C2—C3—C8	−171.88 (16)	C8—C9—C11—C15A	−13.30 (19)
N1—C2—C3—C8	12.2 (2)	C1—C9—C11—C15A	113.98 (16)
O2—C2—C3—C4	9.5 (3)	O3—C9—C11—C12	103.26 (14)
N1—C2—C3—C4	−166.48 (14)	C8—C9—C11—C12	−138.83 (14)
C8—C3—C4—C5	−1.1 (2)	C1—C9—C11—C12	−11.55 (17)
C2—C3—C4—C5	177.51 (16)	O3—C9—C11—C15B	−144.0 (9)
C3—C4—C5—C6	0.3 (3)	C8—C9—C11—C15B	−26.1 (9)
C4—C5—C6—C7	0.8 (3)	C1—C9—C11—C15B	101.2 (9)
C5—C6—C7—C8	−1.1 (3)	N2—C11—C12—C13	−64.30 (16)
C6—C7—C8—C3	0.3 (2)	C15A—C11—C12—C13	55.63 (19)
C6—C7—C8—C9	177.18 (15)	C15B—C11—C12—C13	66.5 (13)
C4—C3—C8—C7	0.8 (2)	C9—C11—C12—C13	−178.36 (13)
C2—C3—C8—C7	−177.81 (15)	C11—C12—C13—S1	145.74 (12)
C4—C3—C8—C9	−176.15 (14)	C14—S1—C13—C12	61.63 (15)
C2—C3—C8—C9	5.2 (2)	C16A—O4A—C15A—O5A	−4.5 (5)
C10—O3—C9—C8	−108.91 (14)	C16A—O4A—C15A—C11	175.0 (2)
C10—O3—C9—C1	127.45 (13)	N2—C11—C15A—O5A	−8.1 (4)
C10—O3—C9—C11	11.32 (15)	C12—C11—C15A—O5A	−126.9 (4)
C7—C8—C9—O3	33.2 (2)	C15B—C11—C15A—O5A	178 (7)
C3—C8—C9—O3	−149.93 (13)	C9—C11—C15A—O5A	105.2 (4)
C7—C8—C9—C1	154.22 (15)	N2—C11—C15A—O4A	172.3 (2)
C3—C8—C9—C1	−28.89 (19)	C12—C11—C15A—O4A	53.5 (3)
C7—C8—C9—C11	−79.87 (18)	C15B—C11—C15A—O4A	−2(7)
C3—C8—C9—C11	97.02 (16)	C9—C11—C15A—O4A	−74.4 (3)
O1—C1—C9—O3	−28.3 (2)	C16B—O4B—C15B—O5B	7(7)
N1—C1—C9—O3	158.75 (13)	C16B—O4B—C15B—C11	−180 (2)
O1—C1—C9—C8	−150.20 (15)	N2—C11—C15B—O5B	163 (3)
N1—C1—C9—C8	36.83 (18)	C15A—C11—C15B—O5B	169 (11)
O1—C1—C9—C11	82.28 (18)	C12—C11—C15B—O5B	42 (4)
N1—C1—C9—C11	−90.69 (15)	C9—C11—C15B—O5B	−79 (4)
C11—N2—C10—O3	−4.9 (2)	N2—C11—C15B—O4B	−11 (4)
C11—N2—C10—C17	174.1 (2)	C15A—C11—C15B—O4B	−5(5)
C9—O3—C10—N2	−5.1 (2)	C12—C11—C15B—O4B	−132 (3)
C9—O3—C10—C17	175.80 (17)	C9—C11—C15B—O4B	107 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18C···O2i	0.96	2.49	3.436 (2)	167.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18C⋯O2i	0.96	2.49	3.436 (2)	167

Symmetry code: (i) .