




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810010469/is2531sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810010469/is2531Isup2.hkl |
CCDC reference: 774357
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean
(C-C) = 0.001 Å
- R factor = 0.031
- wR factor = 0.108
- Data-to-parameter ratio = 20.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 3 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 28 PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 10
Alert level G PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 1 PLAT793_ALERT_4_G The Model has Chirality at C9 (Verify) .... S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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.
All the H atoms were located in a difference Fourier map and allowed to refine freely. Refined distances: C—H = 0.917 (16)–0.994 (15) Å.
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).
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 monochromator | 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 |
C16H16N2O3S | V = 1458.7 (2) Å3 |
Mr = 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)° |
Bruker SMART APEX DUO CCD area-detector diffractometer | 5260 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4752 reflections with I > 2σ(I) |
Tmin = 0.887, Tmax = 0.979 | Rint = 0.024 |
20742 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.108 | All H-atom parameters refined |
S = 1.14 | Δρmax = 0.69 e Å−3 |
5260 reflections | Δρmin = −0.47 e Å−3 |
263 parameters |
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) |
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 |
Mr | 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) |
Tmin, Tmax | 0.887, 0.979 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20742, 5260, 4752 |
Rint | 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 |
Δρmax, Δρmin (e Å−3) | 0.69, −0.47 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
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) −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. |
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.