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

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

doi:10.1107/S1600536810011141

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages o964-o965

doi:10.1107/S1600536810011141

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4-[(2,5-Dimethyl-1,3-thiazol-4-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 22 March 2010; accepted 24 March 2010; online 27 March 2010)

In the title isoquinolinedione compound, C₁₆H₁₆N₂O₃S, the piperidine ring in the tetrahydroisoquinoline ring system adopts a half-boat conformation. The essentially planar thiazole ring [maximum deviation = 0.007 (2) Å] makes a dihedral angle of 34.49 (7)° with the mean plane through the tetrahydroisoquinoline ring system. In the crystal structure, two neighbouring molecules are linked via pairs of O—H⋯N and C—H⋯O hydrogen bonds into inversion-related dimers incorporating R₂²(9) hydrogen-bond ring motifs. These dimers are further linked by weak intermolecular C—H⋯π interactions.

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. (2010a ,b ,c ); 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 = 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[F² > 2σ(F²)] = 0.041
wR(F²) = 0.135
S = 1.33
2343 reflections
264 parameters
All H-atom parameters refined
Δρ_max = 0.87 e Å⁻³
Δρ_min = −1.01 e Å⁻³

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) -x+1, -y+2, -z+2; (ii) -x+1, -y+1, -z+2; (iii) -x+2, -y+2, -z+2.

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/S1600536810011141/sj2758sup1.cif

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

checkCIF report

Comment top

Photo-induced reactions between carbonyl groups acting as electron acceptors and substituted oxazoles as electron donors have been reported to proceed via [2+2] (Griesbeck et al., 2003) or [4+4] photocycloaddition reactions (Zhang et al., 2004). 1,3,4(2H)-Isoquinolinetrione derivatives have been used as carbonyl containing systems to take part in the photo-induced reactions with acetylenes (Zhang et al., 2000). The reaction between 1,3,4(2H)-isoquinolinetrione and toluene gave the H-abstracted product (Suau & Villatoro, 1994). Hence the compounds containing functional groups with similar bond energy, for example, allyl or aldehyde, may give rise to photo-induced H-abstracted reaction. The crystal structure of Z-2-methyl-3'-phenyl-spiro[isoquinoline-4,2'-oxirane]-1,3-dione has been reported (Wang et al., 2000). This paper reports the structure of the title compound, a typical H-abstracted product of the photoreaction between a carbonyl derivative and a thiazole.

In the title isoquinolinedione compound (Fig. 1), atom C9 is the chiral center. The piperidine ring (C1/N1/C2/C3/C8/C9) of the tetrahydroisoquinoline ring system adopts a half-boat conformation (Cremer & Pople, 1975) with puckering parameters of Q = 0.2975 (19) Å, θ = 70.7 (3)° and ϕ = 115.7 (4)° . The thiazol ring (C11/C12/S1/C13/N2) is essentially planar, with maximum deviation of 0.007 (2) Å at atom N2. The dihedral angle formed between the mean planes of the thiazol ring and the tetrahydroisoquinoline ring system is 34.49 (7)°. Bond lengths and angles are consistent with those in related isoquinoline-1,3-dione structures (Fun et al. 2010a,b,c; Zhang et al., 2004).

In the crystal structure (Fig. 2), two inversion-related molecules are linked into dimers incorporating of R²₂(9) hydrogen-bond ring motifs (Bernstein et al., 1995) by O3—H1O3···N2 and C10—H10A···O1 hydrogen bonds (Table 1). These dimers are further interconnected by weak C14—H14B···Cg1 and C15—H15B···Cg2 interactions (Table 1) [Cg1 and Cg2 are the centroids of the C3-C8 benzene ring and the thiazol ring, respectively].

Related literature top

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. (2010a,b,c); 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 (1 mmol, 189 mg) and 2,4,5-trimethyl thiazoles (6 mmol, 762 mg) in dry acetonitrile (50 ml) under 400 nm photo-irradiation. The compound was purified by flash column chromatography with ethyl acetate and petroleum ether (1:4, v:v). X-ray quality single crystals of the title compound were obtained through slow evaporation of solvents from a solution of acetone and petroleum ether (1:5, v:v).

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 30% probability level.
	Fig. 2. The crystal structure of the title compound, viewed along the c axis, showing the molecules linked into dimers. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

4-[(2,5-Dimethyl-1,3-thiazol-4-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 = 1.466 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

Data collection top

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

Refinement top

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(F_o²) + (0.0848P)² + 0.3552P] where P = (F_o² + 2F_c²)/3
S = 1.33	(Δ/σ)_max = 0.001
2343 reflections	Δρ_max = 0.87 e Å⁻³
264 parameters	Δρ_min = −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)

Crystal data top

C₁₆H₁₆N₂O₃S	V = 1433.09 (5) Å³
M_r = 316.37	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.5793 (2) Å	µ = 2.14 mm⁻¹
b = 10.4438 (2) Å	T = 100 K
c = 17.5496 (3) Å	0.32 × 0.19 × 0.12 mm
β = 114.304 (1)°

Data collection top

Bruker SMART APEX DUO CCD area-detector diffractometer	2343 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2311 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.782	R_int = 0.021
22926 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.135	All H-atom parameters refined
S = 1.33	Δρ_max = 0.87 e Å⁻³
2343 reflections	Δρ_min = −1.01 e Å⁻³
264 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	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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+2, −z+2.

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)	8.5793 (2), 10.4438 (2), 17.5496 (3)
β (°)	114.304 (1)
V (Å³)	1433.09 (5)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.32 × 0.19 × 0.12

Data collection
Diffractometer	Bruker SMART APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.546, 0.782
No. of measured, independent and observed [I > 2σ(I)] reflections	22926, 2343, 2311
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.588

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.135, 1.33
No. of reflections	2343
No. of parameters	264
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.87, −1.01

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+2, −z+2; (ii) −x+1, −y+1, −z+2; (iii) −x+2, −y+2, −z+2.

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 of 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 o964-o965

doi:10.1107/S1600536810011141

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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