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

In the title isoquinoline-dione derivative, C(16)H(16)N(2)O(3)S, the piperidine ring in the tetra-hydro-isoquinoline ring system adopts a distorted envelope conformation. The thia-zole ring is essentially planar [maximum deviation = 0.004 (1) Å] and is inclined at a dihedral angle of 31.08 (3)° with respect to the mean plane through the tetra-hydro-isoquinoline ring system. In the crystal structure, inter-molecular O-H⋯O and C-H⋯O inter-actions link adjacent mol-ecules into a three-dimensional extended network. The crystal structure is further stabilized by weak C-H⋯π inter-actions.

Related literature

For general background to and applications of isoquinoline­dione derivatives, see: Griesbeck et al. (2003 ▶); Hall et al. (1994 ▶); Malamas & Hohman (1994 ▶); Suau & Villatoro (1994 ▶); Zhang et al. (2004 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). 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 = 10.2424 (8) Å

b = 15.0438 (13) Å

c = 9.4786 (8) Å

β = 92.839 (2)°

V = 1458.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 100 K

0.52 × 0.26 × 0.09 mm

Data collection

Bruker SMART APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.887, T max = 0.979

20742 measured reflections

5260 independent reflections

4752 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.108

S = 1.14

5260 reflections

263 parameters

All H-atom parameters refined

Δρmax = 0.69 e Å−3

Δρmin = −0.47 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/S1600536810010469/is2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010469/is2531Isup2.hkl

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

C16H16N2O3S	F(000) = 664
Mr = 316.37	Dx = 1.441 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9887 reflections
a = 10.2424 (8) Å	θ = 2.5–35.1°
b = 15.0438 (13) Å	µ = 0.24 mm−1
c = 9.4786 (8) Å	T = 100 K
β = 92.839 (2)°	Block, colourless
V = 1458.7 (2) Å3	0.52 × 0.26 × 0.09 mm
Z = 4

Bruker SMART APEX DUO CCD area-detector diffractometer	5260 independent reflections
Radiation source: fine-focus sealed tube	4752 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 32.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.887, Tmax = 0.979	k = −21→22
20742 measured reflections	l = −14→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	All H-atom parameters refined
S = 1.14	w = 1/[σ2(Fo2) + (0.0649P)2 + 0.2915P] where P = (Fo2 + 2Fc2)/3
5260 reflections	(Δ/σ)max = 0.001
263 parameters	Δρmax = 0.69 e Å−3
0 restraints	Δρmin = −0.47 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
S1	0.86697 (2)	0.201051 (14)	0.69225 (2)	0.01443 (7)
O1	0.38478 (7)	0.29484 (4)	0.78648 (8)	0.01610 (14)
O2	0.46407 (7)	0.59074 (5)	0.82383 (8)	0.01766 (14)
O3	0.57054 (7)	0.27421 (4)	0.59312 (7)	0.01403 (13)
N1	0.42666 (7)	0.44221 (5)	0.81117 (8)	0.01168 (13)
N2	1.03523 (7)	0.32678 (5)	0.71641 (8)	0.01323 (14)
C1	0.45580 (8)	0.35744 (5)	0.76386 (9)	0.01077 (14)
C2	0.49293 (8)	0.51881 (6)	0.77347 (9)	0.01180 (14)
C3	0.59432 (8)	0.50884 (5)	0.66814 (9)	0.01079 (14)
C4	0.64725 (9)	0.58622 (6)	0.61172 (10)	0.01449 (16)
C5	0.73988 (9)	0.57934 (6)	0.51012 (10)	0.01681 (17)
C6	0.77833 (9)	0.49566 (6)	0.46357 (10)	0.01545 (16)
C7	0.72519 (9)	0.41869 (6)	0.51860 (9)	0.01266 (15)
C8	0.63326 (8)	0.42498 (5)	0.62248 (8)	0.01004 (14)
C9	0.58517 (8)	0.34274 (5)	0.69351 (8)	0.00987 (14)
C10	0.68361 (8)	0.31399 (6)	0.81709 (9)	0.01249 (15)
C11	0.81935 (8)	0.29894 (5)	0.77079 (9)	0.01180 (15)
C12	0.92179 (8)	0.35759 (6)	0.77307 (9)	0.01249 (15)
C13	1.02070 (8)	0.24530 (6)	0.66982 (9)	0.01282 (15)
C14	0.31069 (9)	0.45045 (6)	0.89534 (10)	0.01658 (17)
C15	0.92066 (10)	0.45085 (7)	0.82696 (11)	0.01856 (18)
C16	1.12481 (9)	0.19431 (6)	0.59986 (11)	0.01685 (17)
H4A	0.6166 (16)	0.6451 (12)	0.6429 (18)	0.032 (4)*
H5A	0.7767 (17)	0.6330 (12)	0.4682 (18)	0.032 (4)*
H6A	0.8450 (15)	0.4910 (11)	0.3912 (16)	0.022 (4)*
H7A	0.7529 (14)	0.3644 (11)	0.4837 (16)	0.022 (4)*
H10A	0.6458 (14)	0.2612 (11)	0.8585 (15)	0.020 (3)*
H10B	0.6861 (14)	0.3595 (10)	0.8887 (15)	0.018 (3)*
H14A	0.2427 (16)	0.4203 (11)	0.8507 (16)	0.023 (4)*
H14B	0.2864 (18)	0.5111 (13)	0.8938 (19)	0.038 (5)*
H14C	0.3297 (17)	0.4255 (12)	0.9861 (18)	0.032 (4)*
H15A	1.0023 (19)	0.4647 (13)	0.870 (2)	0.040 (5)*
H15B	0.9089 (19)	0.4918 (15)	0.751 (2)	0.048 (5)*
H15C	0.8533 (19)	0.4625 (13)	0.886 (2)	0.041 (5)*
H16A	1.1181 (16)	0.2067 (11)	0.5008 (17)	0.027 (4)*
H16B	1.2092 (17)	0.2095 (11)	0.6394 (18)	0.030 (4)*
H16C	1.1129 (18)	0.1315 (14)	0.6097 (19)	0.037 (5)*
H1O3	0.544 (2)	0.2340 (15)	0.629 (2)	0.043 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01309 (11)	0.00929 (11)	0.02129 (12)	0.00031 (6)	0.00483 (8)	0.00026 (7)
O1	0.0134 (3)	0.0105 (3)	0.0246 (3)	−0.0022 (2)	0.0038 (2)	0.0018 (2)
O2	0.0202 (3)	0.0099 (3)	0.0233 (3)	0.0007 (2)	0.0050 (3)	−0.0041 (2)
O3	0.0196 (3)	0.0086 (3)	0.0142 (3)	−0.0027 (2)	0.0042 (2)	−0.0027 (2)
N1	0.0116 (3)	0.0093 (3)	0.0144 (3)	−0.0001 (2)	0.0033 (2)	−0.0007 (2)
N2	0.0117 (3)	0.0124 (3)	0.0156 (3)	0.0014 (2)	0.0013 (2)	−0.0018 (2)
C1	0.0104 (3)	0.0092 (3)	0.0127 (3)	0.0004 (2)	0.0007 (2)	0.0003 (3)
C2	0.0123 (3)	0.0093 (3)	0.0138 (3)	0.0000 (3)	0.0000 (3)	−0.0005 (3)
C3	0.0114 (3)	0.0088 (3)	0.0121 (3)	−0.0007 (3)	0.0004 (3)	0.0008 (2)
C4	0.0160 (4)	0.0091 (3)	0.0184 (4)	−0.0016 (3)	0.0006 (3)	0.0020 (3)
C5	0.0181 (4)	0.0135 (4)	0.0189 (4)	−0.0033 (3)	0.0023 (3)	0.0048 (3)
C6	0.0163 (4)	0.0160 (4)	0.0143 (3)	−0.0022 (3)	0.0032 (3)	0.0034 (3)
C7	0.0141 (3)	0.0124 (3)	0.0116 (3)	−0.0008 (3)	0.0020 (3)	0.0007 (3)
C8	0.0110 (3)	0.0091 (3)	0.0101 (3)	−0.0009 (2)	0.0002 (2)	0.0009 (2)
C9	0.0111 (3)	0.0074 (3)	0.0111 (3)	−0.0002 (2)	0.0018 (2)	−0.0001 (2)
C10	0.0119 (3)	0.0139 (3)	0.0118 (3)	0.0028 (3)	0.0030 (3)	0.0027 (3)
C11	0.0119 (3)	0.0115 (3)	0.0121 (3)	0.0021 (3)	0.0020 (3)	0.0014 (2)
C12	0.0117 (3)	0.0128 (3)	0.0129 (3)	0.0020 (3)	0.0003 (3)	−0.0022 (3)
C13	0.0120 (3)	0.0113 (3)	0.0154 (3)	0.0010 (3)	0.0027 (3)	0.0005 (3)
C14	0.0144 (4)	0.0163 (4)	0.0197 (4)	0.0002 (3)	0.0075 (3)	−0.0016 (3)
C15	0.0156 (4)	0.0162 (4)	0.0237 (4)	0.0015 (3)	−0.0007 (3)	−0.0087 (3)
C16	0.0150 (4)	0.0126 (4)	0.0234 (4)	0.0022 (3)	0.0060 (3)	−0.0022 (3)

S1—C11	1.7311 (9)	C6—H6A	0.994 (15)
S1—C13	1.7323 (9)	C7—C8	1.3988 (11)
O1—C1	1.2155 (10)	C7—H7A	0.931 (16)
O2—C2	1.2248 (10)	C8—C9	1.5031 (11)
O3—C9	1.4059 (10)	C9—C10	1.5681 (12)
O3—H1O3	0.75 (2)	C10—C11	1.4957 (12)
N1—C1	1.3891 (11)	C10—H10A	0.974 (16)
N1—C2	1.3930 (11)	C10—H10B	0.964 (15)
N1—C14	1.4685 (11)	C11—C12	1.3703 (12)
N2—C13	1.3089 (11)	C12—C15	1.4933 (13)
N2—C12	1.3839 (11)	C13—C16	1.4951 (12)
C1—C9	1.5287 (11)	C14—H14A	0.917 (16)
C2—C3	1.4834 (12)	C14—H14B	0.95 (2)
C3—C8	1.3984 (11)	C14—H14C	0.950 (17)
C3—C4	1.4012 (12)	C15—H15A	0.94 (2)
C4—C5	1.3888 (13)	C15—H15B	0.95 (2)
C4—H4A	0.990 (18)	C15—H15C	0.928 (19)
C5—C6	1.3970 (14)	C16—H16A	0.957 (16)
C5—H5A	0.983 (18)	C16—H16B	0.953 (18)
C6—C7	1.3919 (12)	C16—H16C	0.96 (2)
C11—S1—C13	90.17 (4)	C1—C9—C10	104.67 (6)
C9—O3—H1O3	108.5 (16)	C11—C10—C9	113.28 (7)
C1—N1—C2	124.16 (7)	C11—C10—H10A	112.9 (9)
C1—N1—C14	116.45 (7)	C9—C10—H10A	105.8 (9)
C2—N1—C14	119.14 (7)	C11—C10—H10B	108.8 (9)
C13—N2—C12	111.16 (7)	C9—C10—H10B	108.9 (9)
O1—C1—N1	120.95 (8)	H10A—C10—H10B	107.0 (13)
O1—C1—C9	120.27 (8)	C12—C11—C10	128.32 (8)
N1—C1—C9	118.58 (7)	C12—C11—S1	108.83 (6)
O2—C2—N1	120.06 (8)	C10—C11—S1	122.73 (7)
O2—C2—C3	122.83 (8)	C11—C12—N2	115.80 (8)
N1—C2—C3	117.08 (7)	C11—C12—C15	126.26 (8)
C8—C3—C4	120.65 (8)	N2—C12—C15	117.92 (8)
C8—C3—C2	121.30 (7)	N2—C13—C16	123.95 (8)
C4—C3—C2	118.02 (7)	N2—C13—S1	114.04 (6)
C5—C4—C3	119.55 (8)	C16—C13—S1	122.00 (7)
C5—C4—H4A	120.7 (10)	N1—C14—H14A	108.9 (10)
C3—C4—H4A	119.7 (10)	N1—C14—H14B	107.0 (11)
C4—C5—C6	119.94 (8)	H14A—C14—H14B	106.1 (15)
C4—C5—H5A	120.5 (10)	N1—C14—H14C	108.9 (10)
C6—C5—H5A	119.5 (10)	H14A—C14—H14C	109.9 (14)
C7—C6—C5	120.65 (8)	H14B—C14—H14C	115.9 (16)
C7—C6—H6A	119.7 (9)	C12—C15—H15A	109.7 (12)
C5—C6—H6A	119.7 (9)	C12—C15—H15B	110.7 (13)
C6—C7—C8	119.79 (8)	H15A—C15—H15B	105.4 (17)
C6—C7—H7A	117.7 (9)	C12—C15—H15C	113.7 (12)
C8—C7—H7A	122.5 (9)	H15A—C15—H15C	111.5 (16)
C3—C8—C7	119.41 (7)	H15B—C15—H15C	105.4 (16)
C3—C8—C9	119.94 (7)	C13—C16—H16A	108.5 (10)
C7—C8—C9	120.44 (7)	C13—C16—H16B	110.9 (10)
O3—C9—C8	109.07 (7)	H16A—C16—H16B	111.1 (14)
O3—C9—C1	109.61 (7)	C13—C16—H16C	111.4 (11)
C8—C9—C1	112.75 (7)	H16A—C16—H16C	106.5 (14)
O3—C9—C10	110.26 (7)	H16B—C16—H16C	108.4 (15)
C8—C9—C10	110.41 (7)
C2—N1—C1—O1	−170.99 (8)	C7—C8—C9—C1	−160.42 (7)
C14—N1—C1—O1	3.16 (12)	C3—C8—C9—C10	−91.86 (9)
C2—N1—C1—C9	14.15 (12)	C7—C8—C9—C10	82.90 (9)
C14—N1—C1—C9	−171.71 (7)	O1—C1—C9—O3	35.47 (11)
C1—N1—C2—O2	−177.44 (8)	N1—C1—C9—O3	−149.63 (7)
C14—N1—C2—O2	8.56 (13)	O1—C1—C9—C8	157.17 (8)
C1—N1—C2—C3	4.55 (12)	N1—C1—C9—C8	−27.93 (10)
C14—N1—C2—C3	−169.45 (8)	O1—C1—C9—C10	−82.79 (9)
O2—C2—C3—C8	174.08 (8)	N1—C1—C9—C10	92.12 (9)
N1—C2—C3—C8	−7.97 (12)	O3—C9—C10—C11	64.06 (9)
O2—C2—C3—C4	−8.02 (13)	C8—C9—C10—C11	−56.54 (9)
N1—C2—C3—C4	169.93 (8)	C1—C9—C10—C11	−178.13 (7)
C8—C3—C4—C5	−0.41 (13)	C9—C10—C11—C12	94.19 (11)
C2—C3—C4—C5	−178.32 (8)	C9—C10—C11—S1	−81.38 (9)
C3—C4—C5—C6	0.84 (14)	C13—S1—C11—C12	0.55 (7)
C4—C5—C6—C7	−0.35 (14)	C13—S1—C11—C10	176.87 (7)
C5—C6—C7—C8	−0.59 (13)	C10—C11—C12—N2	−176.72 (8)
C4—C3—C8—C7	−0.53 (12)	S1—C11—C12—N2	−0.66 (10)
C2—C3—C8—C7	177.31 (7)	C10—C11—C12—C15	1.63 (15)
C4—C3—C8—C9	174.28 (8)	S1—C11—C12—C15	177.69 (8)
C2—C3—C8—C9	−7.87 (12)	C13—N2—C12—C11	0.41 (11)
C6—C7—C8—C3	1.02 (13)	C13—N2—C12—C15	−178.08 (8)
C6—C7—C8—C9	−173.77 (8)	C12—N2—C13—C16	178.59 (8)
C3—C8—C9—O3	146.83 (8)	C12—N2—C13—S1	0.04 (10)
C7—C8—C9—O3	−38.41 (10)	C11—S1—C13—N2	−0.35 (7)
C3—C8—C9—C1	24.83 (10)	C11—S1—C13—C16	−178.93 (8)

Cg1 is the centroid of C3–C8 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O3···O2i	0.75 (2)	2.20 (2)	2.8967 (10)	154 (2)
C4—H4A···O1ii	0.990 (18)	2.350 (18)	3.3045 (11)	161.7 (13)
C10—H10A···O3iii	0.975 (16)	2.448 (14)	3.2012 (11)	133.8 (12)
C16—H16B···O1iv	0.953 (17)	2.565 (17)	3.4698 (12)	158.7 (13)
C15—H15B···Cg1	0.95 (2)	2.812 (19)	3.4494 (11)	125.3 (15)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of C3–C8 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O3⋯O2i	0.75 (2)	2.20 (2)	2.8967 (10)	154 (2)
C4—H4A⋯O1ii	0.990 (18)	2.350 (18)	3.3045 (11)	161.7 (13)
C10—H10A⋯O3iii	0.975 (16)	2.448 (14)	3.2012 (11)	133.8 (12)
C16—H16B⋯O1iv	0.953 (17)	2.565 (17)	3.4698 (12)	158.7 (13)
C15—H15B⋯Cg1	0.95 (2)	2.812 (19)	3.4494 (11)	125.3 (15)

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