4-[(2,5-Dimethyl-1,3-thia-zol-4-yl)meth-yl]-4-hydr-oxy-2-methyl-isoquinoline-1,3(2H,4H)-dione.

In the title isoquinoline-dione compound, C(16)H(16)N(2)O(3)S, the piperidine ring in the tetra-hydro-isoquinoline ring system adopts a half-boat conformation. The essentially planar thia-zole ring [maximum deviation = 0.007 (2) Å] makes a dihedral angle of 34.49 (7)° with the mean plane through the tetra-hydro-isoquinoline ring system. In the crystal structure, two neighbouring mol-ecules are linked via pairs of O-H⋯N and C-H⋯O hydrogen bonds into inversion-related dimers incorporating R(2) (2)(9) hydrogen-bond ring motifs. These dimers are further linked by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and applications of isoquinoline­dione derivatives, see: Griesbeck et al. (2003 ▶); Suau & Villatoro (1994 ▶); Zhang et al. (2000 ▶, 2004 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶); Wang et al. (2000 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16N2O3S

M = 316.37

Monoclinic,

a = 8.5793 (2) Å

b = 10.4438 (2) Å

c = 17.5496 (3) Å

β = 114.304 (1)°

V = 1433.09 (5) Å3

Z = 4

Cu Kα radiation

μ = 2.14 mm−1

T = 100 K

0.32 × 0.19 × 0.12 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.546, T max = 0.782

22926 measured reflections

2343 independent reflections

2311 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.135

S = 1.33

2343 reflections

264 parameters

All H-atom parameters refined

Δρmax = 0.87 e Å−3

Δρmin = −1.01 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 datablocks global, I. DOI: 10.1107/S1600536810011141/sj2758sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011141/sj2758Isup2.hkl

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

C16H16N2O3S	F(000) = 664
Mr = 316.37	Dx = 1.466 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 9047 reflections
a = 8.5793 (2) Å	θ = 5.1–67.1°
b = 10.4438 (2) Å	µ = 2.14 mm−1
c = 17.5496 (3) Å	T = 100 K
β = 114.304 (1)°	Block, colourless
V = 1433.09 (5) Å3	0.32 × 0.19 × 0.12 mm
Z = 4

Bruker SMART APEX DUO CCD area-detector diffractometer	2343 independent reflections
Radiation source: fine-focus sealed tube	2311 reflections with I > 2σ(I)
none	Rint = 0.021
φ and ω scans	θmax = 65.0°, θmin = 5.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→8
Tmin = 0.546, Tmax = 0.782	k = −11→12
22926 measured reflections	l = −17→20

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)] = 0.041	All H-atom parameters refined
wR(F2) = 0.135	w = 1/[σ2(Fo2) + (0.0848P)2 + 0.3552P] where P = (Fo2 + 2Fc2)/3
S = 1.33	(Δ/σ)max = 0.001
2343 reflections	Δρmax = 0.87 e Å−3
264 parameters	Δρmin = −1.01 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.034 (2)

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
S1	1.09845 (5)	0.83482 (4)	1.10440 (3)	0.0194 (3)
O1	0.38500 (16)	0.80117 (12)	1.02541 (8)	0.0215 (4)
O2	0.82233 (18)	0.52224 (13)	1.07705 (8)	0.0275 (4)
O3	0.33049 (17)	0.82715 (12)	0.86199 (8)	0.0201 (4)
N1	0.6048 (2)	0.66140 (13)	1.05324 (10)	0.0176 (4)
N2	0.80660 (19)	0.91667 (14)	1.08986 (9)	0.0182 (4)
C1	0.4850 (2)	0.74898 (16)	1.00286 (11)	0.0174 (4)
C2	0.7103 (2)	0.58819 (16)	1.02692 (11)	0.0190 (4)
C3	0.6699 (2)	0.58984 (16)	0.93626 (11)	0.0178 (4)
C4	0.7471 (2)	0.49838 (17)	0.90499 (12)	0.0205 (4)
C5	0.7076 (2)	0.49498 (17)	0.82010 (12)	0.0229 (5)
C6	0.5912 (3)	0.58198 (18)	0.76658 (12)	0.0220 (4)
C7	0.5162 (2)	0.67391 (17)	0.79782 (12)	0.0200 (4)
C8	0.5556 (2)	0.67879 (16)	0.88301 (12)	0.0172 (4)
C9	0.4934 (2)	0.78679 (17)	0.92028 (11)	0.0171 (4)
C10	0.6204 (2)	0.90246 (16)	0.93867 (11)	0.0164 (4)
C11	0.7918 (2)	0.88586 (16)	1.00992 (11)	0.0166 (4)
C12	0.9358 (2)	0.84040 (15)	1.00461 (12)	0.0177 (4)
C13	0.9603 (2)	0.89292 (17)	1.14552 (11)	0.0195 (4)
C14	0.6343 (3)	0.65094 (18)	1.14136 (12)	0.0208 (5)
C15	0.9659 (3)	0.8009 (2)	0.92990 (12)	0.0209 (4)
C16	1.0194 (3)	0.9151 (2)	1.23738 (12)	0.0266 (5)
H4A	0.824 (3)	0.439 (2)	0.9426 (14)	0.023 (5)*
H5A	0.762 (3)	0.433 (2)	0.7991 (15)	0.032 (6)*
H6A	0.563 (3)	0.581 (2)	0.7073 (15)	0.026 (6)*
H7A	0.439 (3)	0.736 (2)	0.7631 (15)	0.027 (6)*
H10A	0.564 (3)	0.975 (2)	0.9491 (13)	0.018 (5)*
H10B	0.633 (3)	0.9172 (19)	0.8877 (14)	0.016 (5)*
H14A	0.541 (4)	0.692 (3)	1.1484 (17)	0.040 (7)*
H14B	0.634 (3)	0.561 (2)	1.1555 (14)	0.025 (5)*
H14C	0.729 (4)	0.693 (3)	1.1756 (17)	0.033 (6)*
H15A	0.988 (3)	0.711 (3)	0.9309 (17)	0.041 (7)*
H15B	1.058 (3)	0.850 (2)	0.9259 (16)	0.033 (6)*
H15C	0.869 (4)	0.820 (3)	0.8790 (19)	0.043 (7)*
H16A	1.029 (4)	1.003 (3)	1.2454 (19)	0.056 (9)*
H16B	0.939 (4)	0.885 (3)	1.2568 (18)	0.046 (7)*
H16C	1.133 (4)	0.878 (3)	1.270 (2)	0.050 (8)*
H1O3	0.297 (4)	0.889 (3)	0.8823 (19)	0.050 (8)*

	U11	U22	U33	U12	U13	U23
S1	0.0153 (4)	0.0216 (4)	0.0198 (4)	0.00071 (15)	0.0057 (2)	−0.00131 (15)
O1	0.0209 (7)	0.0208 (7)	0.0262 (7)	0.0007 (5)	0.0131 (6)	−0.0012 (5)
O2	0.0293 (8)	0.0307 (8)	0.0218 (7)	0.0109 (6)	0.0097 (6)	0.0053 (6)
O3	0.0146 (7)	0.0226 (7)	0.0198 (7)	0.0032 (5)	0.0037 (6)	0.0003 (5)
N1	0.0189 (9)	0.0167 (8)	0.0171 (8)	−0.0009 (6)	0.0075 (7)	−0.0003 (5)
N2	0.0184 (9)	0.0172 (8)	0.0187 (8)	−0.0018 (6)	0.0072 (6)	−0.0016 (6)
C1	0.0160 (9)	0.0146 (8)	0.0206 (9)	−0.0036 (7)	0.0067 (7)	−0.0025 (7)
C2	0.0188 (10)	0.0159 (9)	0.0223 (10)	−0.0005 (7)	0.0085 (8)	0.0004 (7)
C3	0.0173 (10)	0.0161 (9)	0.0209 (9)	−0.0035 (7)	0.0086 (7)	−0.0013 (7)
C4	0.0216 (10)	0.0171 (9)	0.0247 (9)	−0.0003 (7)	0.0112 (8)	0.0009 (7)
C5	0.0278 (11)	0.0181 (9)	0.0280 (10)	−0.0042 (8)	0.0167 (8)	−0.0054 (7)
C6	0.0273 (11)	0.0214 (9)	0.0197 (9)	−0.0079 (7)	0.0122 (8)	−0.0039 (7)
C7	0.0202 (11)	0.0187 (9)	0.0201 (10)	−0.0032 (7)	0.0073 (8)	0.0005 (7)
C8	0.0147 (10)	0.0166 (9)	0.0203 (9)	−0.0043 (6)	0.0073 (7)	−0.0020 (7)
C9	0.0133 (9)	0.0182 (9)	0.0176 (9)	−0.0002 (7)	0.0043 (7)	0.0000 (7)
C10	0.0173 (10)	0.0144 (9)	0.0175 (9)	0.0001 (7)	0.0071 (8)	0.0007 (7)
C11	0.0179 (10)	0.0130 (9)	0.0188 (9)	−0.0018 (6)	0.0075 (7)	0.0001 (6)
C12	0.0169 (10)	0.0145 (9)	0.0206 (10)	−0.0027 (6)	0.0066 (8)	−0.0002 (6)
C13	0.0180 (10)	0.0185 (9)	0.0221 (9)	−0.0017 (7)	0.0083 (7)	−0.0017 (7)
C14	0.0256 (12)	0.0205 (10)	0.0173 (10)	−0.0019 (8)	0.0098 (9)	0.0001 (7)
C15	0.0187 (10)	0.0234 (10)	0.0218 (10)	−0.0010 (8)	0.0095 (8)	−0.0012 (8)
C16	0.0220 (11)	0.0356 (12)	0.0202 (10)	0.0005 (9)	0.0065 (9)	−0.0045 (8)

S1—C13	1.7317 (18)	C6—H6A	0.97 (2)
S1—C12	1.7337 (19)	C7—C8	1.391 (3)
O1—C1	1.212 (2)	C7—H7A	0.95 (3)
O2—C2	1.215 (2)	C8—C9	1.508 (2)
O3—C9	1.414 (2)	C9—C10	1.569 (2)
O3—H1O3	0.84 (3)	C10—C11	1.497 (2)
N1—C1	1.388 (2)	C10—H10A	0.95 (2)
N1—C2	1.400 (2)	C10—H10B	0.96 (2)
N1—C14	1.465 (2)	C11—C12	1.363 (3)
N2—C13	1.301 (2)	C12—C15	1.495 (3)
N2—C11	1.393 (2)	C13—C16	1.495 (3)
C1—C9	1.532 (2)	C14—H14A	0.96 (3)
C2—C3	1.482 (3)	C14—H14B	0.97 (3)
C3—C8	1.394 (3)	C14—H14C	0.90 (3)
C3—C4	1.397 (3)	C15—H15A	0.95 (3)
C4—C5	1.386 (3)	C15—H15B	0.97 (3)
C4—H4A	0.95 (2)	C15—H15C	0.96 (3)
C5—C6	1.390 (3)	C16—H16A	0.93 (3)
C5—H5A	0.96 (3)	C16—H16B	0.94 (3)
C6—C7	1.388 (3)	C16—H16C	0.98 (3)
C13—S1—C12	90.28 (9)	C1—C9—C10	107.64 (14)
C9—O3—H1O3	109 (2)	C11—C10—C9	116.27 (14)
C1—N1—C2	124.01 (15)	C11—C10—H10A	109.3 (13)
C1—N1—C14	118.86 (15)	C9—C10—H10A	106.8 (13)
C2—N1—C14	116.94 (15)	C11—C10—H10B	110.6 (13)
C13—N2—C11	110.88 (15)	C9—C10—H10B	105.4 (13)
O1—C1—N1	121.76 (16)	H10A—C10—H10B	108.0 (17)
O1—C1—C9	120.54 (16)	C12—C11—N2	116.10 (16)
N1—C1—C9	117.49 (15)	C12—C11—C10	126.12 (16)
O2—C2—N1	119.78 (16)	N2—C11—C10	117.76 (15)
O2—C2—C3	123.34 (16)	C11—C12—C15	130.18 (18)
N1—C2—C3	116.76 (15)	C11—C12—S1	108.55 (14)
C8—C3—C4	120.56 (17)	C15—C12—S1	121.27 (14)
C8—C3—C2	121.10 (16)	N2—C13—C16	124.69 (17)
C4—C3—C2	118.33 (16)	N2—C13—S1	114.19 (13)
C5—C4—C3	119.64 (17)	C16—C13—S1	121.11 (14)
C5—C4—H4A	121.7 (13)	N1—C14—H14A	108.1 (17)
C3—C4—H4A	118.7 (13)	N1—C14—H14B	108.9 (13)
C4—C5—C6	119.94 (17)	H14A—C14—H14B	108 (2)
C4—C5—H5A	119.3 (15)	N1—C14—H14C	112.7 (16)
C6—C5—H5A	120.7 (15)	H14A—C14—H14C	105 (2)
C7—C6—C5	120.40 (17)	H14B—C14—H14C	113 (2)
C7—C6—H6A	118.9 (13)	C12—C15—H15A	111.0 (16)
C5—C6—H6A	120.7 (13)	C12—C15—H15B	111.1 (15)
C6—C7—C8	120.17 (17)	H15A—C15—H15B	111 (2)
C6—C7—H7A	122.3 (14)	C12—C15—H15C	111.2 (17)
C8—C7—H7A	117.5 (14)	H15A—C15—H15C	108 (2)
C7—C8—C3	119.26 (16)	H15B—C15—H15C	104 (2)
C7—C8—C9	121.39 (16)	C13—C16—H16A	106.6 (19)
C3—C8—C9	118.99 (16)	C13—C16—H16B	111.3 (18)
O3—C9—C8	109.28 (15)	H16A—C16—H16B	108 (3)
O3—C9—C1	110.12 (14)	C13—C16—H16C	112.4 (18)
C8—C9—C1	112.37 (14)	H16A—C16—H16C	107 (3)
O3—C9—C10	108.37 (14)	H16B—C16—H16C	111 (3)
C8—C9—C10	108.97 (14)
C2—N1—C1—O1	172.72 (16)	C3—C8—C9—C1	−30.6 (2)
C14—N1—C1—O1	−12.4 (2)	C7—C8—C9—C10	−84.4 (2)
C2—N1—C1—C9	−12.5 (2)	C3—C8—C9—C10	88.64 (19)
C14—N1—C1—C9	162.30 (16)	O1—C1—C9—O3	−30.9 (2)
C1—N1—C2—O2	173.39 (17)	N1—C1—C9—O3	154.29 (15)
C14—N1—C2—O2	−1.5 (2)	O1—C1—C9—C8	−152.96 (16)
C1—N1—C2—C3	−10.5 (2)	N1—C1—C9—C8	32.2 (2)
C14—N1—C2—C3	174.59 (15)	O1—C1—C9—C10	87.05 (19)
O2—C2—C3—C8	−171.67 (18)	N1—C1—C9—C10	−87.76 (18)
N1—C2—C3—C8	12.4 (2)	O3—C9—C10—C11	169.71 (14)
O2—C2—C3—C4	9.4 (3)	C8—C9—C10—C11	−71.47 (19)
N1—C2—C3—C4	−166.57 (16)	C1—C9—C10—C11	50.6 (2)
C8—C3—C4—C5	−0.9 (3)	C13—N2—C11—C12	−1.1 (2)
C2—C3—C4—C5	177.98 (16)	C13—N2—C11—C10	177.57 (15)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C11—C12	92.3 (2)
C4—C5—C6—C7	1.1 (3)	C9—C10—C11—N2	−86.14 (19)
C5—C6—C7—C8	−0.7 (3)	N2—C11—C12—C15	−178.82 (17)
C6—C7—C8—C3	−0.5 (3)	C10—C11—C12—C15	2.7 (3)
C6—C7—C8—C9	172.49 (17)	N2—C11—C12—S1	0.32 (19)
C4—C3—C8—C7	1.4 (3)	C10—C11—C12—S1	−178.19 (14)
C2—C3—C8—C7	−177.54 (16)	C13—S1—C12—C11	0.35 (13)
C4—C3—C8—C9	−171.82 (16)	C13—S1—C12—C15	179.58 (15)
C2—C3—C8—C9	9.3 (2)	C11—N2—C13—C16	179.99 (17)
C7—C8—C9—O3	33.9 (2)	C11—N2—C13—S1	1.32 (19)
C3—C8—C9—O3	−153.11 (15)	C12—S1—C13—N2	−1.00 (14)
C7—C8—C9—C1	156.42 (16)	C12—S1—C13—C16	−179.72 (16)

Cg1 and Cg2 are the centroids of the C3–C8 benzene ring and the C11/C12/S1/C13/N2 thiazol ring, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···N2i	0.84 (3)	2.35 (3)	3.174 (2)	167 (3)
C10—H10A···O1i	0.96 (2)	2.39 (2)	3.163 (2)	138 (2)
C14—H14B···Cg1ii	0.97 (3)	2.71 (3)	3.403 (2)	129 (2)
C15—H15B···Cg2iii	0.97 (3)	2.89 (2)	3.537 (2)	125.4 (18)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 benzene ring and the C11/C12/S1/C13/N2 thia­zol ring, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯N2i	0.84 (3)	2.35 (3)	3.174 (2)	167 (3)
C10—H10A⋯O1i	0.96 (2)	2.39 (2)	3.163 (2)	138 (2)
C14—H14B⋯Cg1ii	0.97 (3)	2.71 (3)	3.403 (2)	129 (2)
C15—H15B⋯Cg2iii	0.97 (3)	2.89 (2)	3.537 (2)	125.4 (18)

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