4-[(2,4-Dimethyl­thia­zol-5-yl)meth­yl]-4-hydr­oxy-2-methyl­isoquinoline-1,3(2H,4H)-dione

Fun, H.-K.; Goh, J.H.; Yu, H.; Zhang, Y.

doi:10.1107/S1600536810010469

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o940-o941

doi:10.1107/S1600536810010469

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4-[(2,4-Dimethylthiazol-5-yl)methyl]-4-hydroxy-2-methylisoquinoline-1,3(2H,4H)-dione

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Haitao Yu ^b and Yan Zhang ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 17 March 2010; accepted 20 March 2010; online 27 March 2010)

In the title isoquinolinedione derivative, C₁₆H₁₆N₂O₃S, the piperidine ring in the tetrahydroisoquinoline ring system adopts a distorted envelope conformation. The thiazole 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 tetrahydroisoquinoline ring system. In the crystal structure, intermolecular O—H⋯O and C—H⋯O interactions link adjacent molecules into a three-dimensional extended network. The crystal structure is further stabilized by weak C—H⋯π interactions.

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. (2010a ,b ); 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_r = 316.37
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.031
wR(F²) = 0.108
S = 1.14
5260 reflections
263 parameters
All H-atom parameters refined
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.47 e Å⁻³

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⋯O1^iv	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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) x+1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010469/is2531sup1.cif

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

checkCIF report

Comment top

1,3,4(2H)-Isoquinolinetrione derivatives have a variety of biological activities and are synthetic precursors for many naturally occurring alkaloids (Hall et al., 1994; Malamas & Hohman, 1994). The carbonyl group on C4 of isoquinoline-1,3,4-trione is an active site for photo-induced reactions with alkenes or other hydrogen donors to give photoaddition products such as oxetanes (Suau & Villatoro, 1994). Oxazole derivatives have been used as electron donor species in the Paternò-Büchi photocycloaddition with carbonyl groups (Griesbeck et al., 2003). Other interesting photo-reactions such as the [4+4] photocycloadditions have also been reported on substituted oxazole with 9,10-phenanthraquinone and 1-acetylisatin (Zhang et al., 2004). The crystal structure of Z-2-methyl-3'-phenyl-spiro[isoquinoline-4,2'-oxirane]-1,3-dione has been reported (Wang et al., 2000). In view of the importance of the title compound as a typical H-abstracted product in photoreaction between carbonyl and thiazoles, the paper reports its crystal structure.

In the title isoquinolinedione derivative (Fig. 1), atom C9 is the chiral center. The piperidine ring (C1/N1/C2/C3/C8/C9) of the tetrahydroisoquinoline ring system adopts a distorted envelope conformation with atom C9 as the flap; the puckering amplitude Q = 0.2512 (9) Å, θ = 113.8 (2)° and ϕ = 291.0 (2)° (Cremer & Pople, 1975). The thiazol ring (C11/C12/N2/C13/S1) is essentially planar, with maximum deviation of 0.004 (1) Å at atom C11, and it inclines at a dihedral angle of 31.08 (3)° with the tetrahydroisoquinoline ring system. Bond lengths and angles are consistent to those observed in related isoquinoline-1,3-dione structures (Fun et al. 2010a,b; Zhang et al., 2004).

In the crystal packing (Fig. 2), intermolecular O3—H1O3···O2, C4—H4A···O1, C10—H10A···O3 and C16—H16B···O1 hydrogen bonds (Table 1) link neighbouring molecules into a three-dimensional extended network. The crystal structure is further stabilized by intermolecular C15—H15B···Cg1 interactions (Table 1) involving the centroid of the C3–C8 benzene ring.

Related literature top

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. (2010a,b); Wang et al. (2000). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

The title compound was obtained in the reaction between 1,3,4(2H)-isoquinolinetrione and 1,4,5-trimethyl thiazoles under photo-irradiation with light of wavelength > 400 nm. The compound was purified by flash column chromatography with ethyl acetate and petroleum ether as eluents. X-ray quality single crystals of the title compound were obtained by slow evaporation of solvents from the solution of the title compound in acetone and petroleum ether.

Computing details top

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

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing the three-dimensional extended network. H atoms not involved in intermolecular interactions have been omitted for clarity.

4-[(2,4-Dimethylthiazol-5-yl)methyl]-4-hydroxy-2-methylisoquinoline- 1,3(2H,4H)-dione top

Crystal data top

C₁₆H₁₆N₂O₃S	F(000) = 664
M_r = 316.37	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0649P)² + 0.2915P] where P = (F_o² + 2F_c²)/3
5260 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₃S	V = 1458.7 (2) Å³
M_r = 316.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.2424 (8) Å	µ = 0.24 mm⁻¹
b = 15.0438 (13) Å	T = 100 K
c = 9.4786 (8) Å	0.52 × 0.26 × 0.09 mm
β = 92.839 (2)°

Data collection top

Bruker SMART APEX DUO CCD area-detector diffractometer	5260 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4752 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.979	R_int = 0.024
20742 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.108	All H-atom parameters refined
S = 1.14	Δρ_max = 0.69 e Å⁻³
5260 reflections	Δρ_min = −0.47 e Å⁻³
263 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₃S
M_r	316.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.2424 (8), 15.0438 (13), 9.4786 (8)
β (°)	92.839 (2)
V (Å³)	1458.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.52 × 0.26 × 0.09

Data collection
Diffractometer	Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.887, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	20742, 5260, 4752
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.108, 1.14
No. of reflections	5260
No. of parameters	263
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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) −x+1, y−1/2, −z+3/2; (ii) −x+1, y+1/2, −z+3/2; (iii) x, −y+1/2, z+1/2; (iv) x+1, y, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for the Research University Golden Goose grant (No. 1001/PFIZIK/811012). Financial support from the Ministry of Science and Technology of China on the Austria–China Cooperation project (2007DFA41590) is acknowledged. JHG also thanks USM for the award of a USM fellowship.

References

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Volume 66| Part 4| April 2010| Pages o940-o941

doi:10.1107/S1600536810010469

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-[(2,4-Di­methyl­thia­zol-5-yl)meth­yl]-4-hydr­­oxy-2-methyl­iso­quinoline-1,3(2H,4H)-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

4-[(2,4-Dimethylthiazol-5-yl)methyl]-4-hydroxy-2-methylisoquinoline-1,3(2H,4H)-dione