organic compounds
Methyl 2-acetamido-2-(4-hydroxy-2-methyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-4-yl)-4-methylpentanoate
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
In the isoquinoline ring system of the title molecule, C19H24N2O6, the N-heterocyclic ring is in a half-boat conformation. The molecular structure is stabilized by an intramolecular O—H⋯O hydrogen bond, which generates an S(7) ring motif. In the crystal, molecules are linked via intermolecular bifurcated N—H⋯(O,O) and weak C—H⋯O hydrogen bonds into a three-dimensional network.
Related literature
For general background to and the potential biological activity of title compound, see: Yu et al. (2010); Huang et al. (2011); Rao et al. (1995); Nagamitsu et al. (1996); Evans & Weber (1986); Heimgartner (1991); Rando (1975); Griesbeck et al. (2003); Zhang et al. (2004); Wang et al. (2010). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For standard bond-length data, see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975). For related structures, see: Fun et al. (2011a,b,c,d). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell 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
10.1107/S1600536811022999/lh5262sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811022999/lh5262Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536811022999/lh5262Isup3.cml
The title compound was the main product from the acid-catalyzed transformation of the photocycloadducts of isoquinoline-1,3,4-trione and 4-isobutyl-5-methoxy-2-methyloxazole. The compound was purified by flash
with ethyl acetate/petroleum ether (1:5) as eluents. X-ray quality crystals of the title compound were obtained from slow evaporation of an acetone and petroleum ether solution (1:8) of the title compound, m.p. 425-427 K.Atoms H1N2 and H1O3 were located in a difference Fourier map and refined freely [N2—H1N2 = 0.92 (2) Å, O3—H1O3 = 0.86 (2) Å]. The remaining H atoms were positioned geometrically and refined using a riding model with C–H = 0.93 - 0.97 Å and Uiso(H) = 1.2 or 1.5 Ueq(C). A rotating-group model was applied for the methyl groups. The highest residual electron density peak is located at 0.20 Å from H16B and the deepest hole is located at 0.78 Å from C9.
Data collection: APEX2 (Bruker, 2009); cell
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).C19H24N2O6 | F(000) = 800 |
Mr = 376.40 | Dx = 1.366 Mg m−3 |
Monoclinic, Cc | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: C -2yc | Cell parameters from 9888 reflections |
a = 17.8256 (15) Å | θ = 5.1–64.2° |
b = 8.7584 (6) Å | µ = 0.85 mm−1 |
c = 11.9182 (8) Å | T = 100 K |
β = 100.404 (5)° | Needle, colourless |
V = 1830.1 (2) Å3 | 0.50 × 0.15 × 0.15 mm |
Z = 4 |
Bruker APEX DUO CCD area-detector diffractometer | 2713 independent reflections |
Radiation source: fine-focus sealed tube | 2673 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 64.7°, θmin = 5.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −20→20 |
Tmin = 0.678, Tmax = 0.883 | k = −9→10 |
18268 measured reflections | l = −12→13 |
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)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.059 | w = 1/[σ2(Fo2) + (0.0319P)2 + 0.7184P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2713 reflections | Δρmax = 0.11 e Å−3 |
257 parameters | Δρmin = −0.14 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 1204 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (13) |
C19H24N2O6 | V = 1830.1 (2) Å3 |
Mr = 376.40 | Z = 4 |
Monoclinic, Cc | Cu Kα radiation |
a = 17.8256 (15) Å | µ = 0.85 mm−1 |
b = 8.7584 (6) Å | T = 100 K |
c = 11.9182 (8) Å | 0.50 × 0.15 × 0.15 mm |
β = 100.404 (5)° |
Bruker APEX DUO CCD area-detector diffractometer | 2713 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 2673 reflections with I > 2σ(I) |
Tmin = 0.678, Tmax = 0.883 | Rint = 0.033 |
18268 measured reflections |
R[F2 > 2σ(F2)] = 0.024 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.059 | Δρmax = 0.11 e Å−3 |
S = 1.05 | Δρmin = −0.14 e Å−3 |
2713 reflections | Absolute structure: Flack (1983), 1204 Friedel pairs |
257 parameters | Absolute structure parameter: 0.05 (13) |
2 restraints |
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 | ||
O1 | 0.81985 (6) | 0.74615 (13) | 1.04040 (10) | 0.0229 (3) | |
O2 | 1.05834 (6) | 0.65801 (14) | 0.97375 (10) | 0.0302 (3) | |
O3 | 0.76692 (6) | 0.48621 (12) | 0.94001 (10) | 0.0204 (2) | |
O4 | 0.91523 (6) | 0.77211 (12) | 0.76247 (9) | 0.0193 (2) | |
O5 | 0.89019 (6) | 0.56633 (12) | 0.65074 (9) | 0.0204 (2) | |
O6 | 0.64674 (6) | 0.52211 (12) | 0.77471 (10) | 0.0223 (3) | |
N1 | 0.93918 (7) | 0.70763 (15) | 1.00450 (11) | 0.0206 (3) | |
N2 | 0.75643 (7) | 0.51865 (14) | 0.70247 (12) | 0.0171 (3) | |
C1 | 0.86194 (9) | 0.67556 (17) | 0.99008 (14) | 0.0188 (3) | |
C2 | 0.99257 (9) | 0.61559 (19) | 0.96548 (14) | 0.0222 (4) | |
C3 | 0.96586 (9) | 0.46387 (18) | 0.91865 (14) | 0.0200 (3) | |
C4 | 1.02036 (9) | 0.3555 (2) | 0.90385 (14) | 0.0253 (4) | |
H4A | 1.0719 | 0.3803 | 0.9194 | 0.030* | |
C5 | 0.99735 (10) | 0.2104 (2) | 0.86574 (15) | 0.0285 (4) | |
H5A | 1.0334 | 0.1376 | 0.8550 | 0.034* | |
C6 | 0.92023 (10) | 0.17437 (19) | 0.84364 (15) | 0.0259 (4) | |
H6A | 0.9049 | 0.0765 | 0.8192 | 0.031* | |
C7 | 0.86576 (9) | 0.28210 (18) | 0.85750 (14) | 0.0217 (3) | |
H7A | 0.8143 | 0.2565 | 0.8424 | 0.026* | |
C8 | 0.88811 (8) | 0.42821 (18) | 0.89389 (13) | 0.0181 (3) | |
C9 | 0.82982 (8) | 0.55120 (17) | 0.90207 (14) | 0.0174 (3) | |
C10 | 0.80278 (8) | 0.62935 (17) | 0.77805 (14) | 0.0167 (3) | |
C11 | 0.76008 (9) | 0.78137 (17) | 0.78789 (13) | 0.0180 (3) | |
H11A | 0.7260 | 0.7664 | 0.8419 | 0.022* | |
H11B | 0.7974 | 0.8574 | 0.8201 | 0.022* | |
C12 | 0.71318 (9) | 0.84730 (17) | 0.67768 (15) | 0.0217 (3) | |
H12A | 0.6734 | 0.7732 | 0.6477 | 0.026* | |
C13 | 0.75969 (10) | 0.8792 (2) | 0.58470 (15) | 0.0285 (4) | |
H13A | 0.7803 | 0.7852 | 0.5620 | 0.043* | |
H13B | 0.8006 | 0.9479 | 0.6135 | 0.043* | |
H13C | 0.7274 | 0.9246 | 0.5201 | 0.043* | |
C14 | 0.67409 (10) | 0.9933 (2) | 0.70714 (17) | 0.0306 (4) | |
H14A | 0.6414 | 1.0315 | 0.6401 | 0.046* | |
H14B | 0.7120 | 1.0686 | 0.7352 | 0.046* | |
H14C | 0.6443 | 0.9716 | 0.7647 | 0.046* | |
C15 | 0.87344 (8) | 0.65099 (17) | 0.72155 (14) | 0.0165 (3) | |
C16 | 0.98383 (9) | 0.79217 (19) | 0.71419 (15) | 0.0230 (4) | |
H16A | 1.0110 | 0.8807 | 0.7472 | 0.035* | |
H16B | 0.9701 | 0.8053 | 0.6331 | 0.035* | |
H16C | 1.0158 | 0.7037 | 0.7304 | 0.035* | |
C17 | 0.68252 (8) | 0.48575 (17) | 0.69911 (14) | 0.0179 (3) | |
C18 | 0.64504 (9) | 0.40140 (19) | 0.59393 (15) | 0.0248 (4) | |
H18A | 0.6056 | 0.3365 | 0.6124 | 0.037* | |
H18B | 0.6824 | 0.3404 | 0.5657 | 0.037* | |
H18C | 0.6232 | 0.4734 | 0.5365 | 0.037* | |
C19 | 0.96743 (10) | 0.84909 (19) | 1.06333 (17) | 0.0300 (4) | |
H19A | 0.9273 | 0.8958 | 1.0952 | 0.045* | |
H19B | 0.9839 | 0.9179 | 1.0100 | 0.045* | |
H19C | 1.0096 | 0.8261 | 1.1233 | 0.045* | |
H1N2 | 0.7798 (11) | 0.479 (2) | 0.6459 (18) | 0.025 (5)* | |
H1O3 | 0.7237 (13) | 0.510 (2) | 0.8986 (18) | 0.037 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0255 (6) | 0.0248 (6) | 0.0184 (7) | 0.0040 (4) | 0.0040 (5) | −0.0020 (5) |
O2 | 0.0178 (6) | 0.0408 (7) | 0.0299 (8) | −0.0067 (5) | −0.0013 (5) | 0.0021 (6) |
O3 | 0.0173 (5) | 0.0267 (6) | 0.0173 (7) | −0.0020 (4) | 0.0036 (5) | 0.0027 (5) |
O4 | 0.0171 (5) | 0.0208 (5) | 0.0201 (7) | −0.0039 (4) | 0.0033 (4) | −0.0013 (5) |
O5 | 0.0191 (5) | 0.0237 (5) | 0.0188 (7) | −0.0013 (4) | 0.0046 (4) | −0.0021 (5) |
O6 | 0.0177 (5) | 0.0279 (6) | 0.0215 (7) | −0.0011 (4) | 0.0045 (5) | −0.0014 (5) |
N1 | 0.0220 (7) | 0.0223 (7) | 0.0162 (8) | −0.0040 (5) | −0.0003 (5) | 0.0005 (6) |
N2 | 0.0163 (7) | 0.0188 (7) | 0.0161 (8) | −0.0006 (5) | 0.0026 (6) | −0.0022 (5) |
C1 | 0.0221 (8) | 0.0190 (7) | 0.0143 (9) | 0.0005 (6) | 0.0004 (6) | 0.0044 (6) |
C2 | 0.0195 (8) | 0.0310 (9) | 0.0143 (9) | −0.0008 (6) | −0.0019 (6) | 0.0057 (7) |
C3 | 0.0206 (8) | 0.0281 (8) | 0.0112 (9) | 0.0010 (6) | 0.0024 (6) | 0.0038 (7) |
C4 | 0.0210 (8) | 0.0383 (10) | 0.0163 (10) | 0.0049 (7) | 0.0027 (7) | 0.0045 (7) |
C5 | 0.0322 (10) | 0.0339 (10) | 0.0193 (11) | 0.0139 (7) | 0.0042 (7) | 0.0002 (7) |
C6 | 0.0352 (10) | 0.0242 (9) | 0.0168 (10) | 0.0055 (7) | 0.0009 (7) | 0.0007 (7) |
C7 | 0.0248 (8) | 0.0246 (8) | 0.0151 (9) | 0.0009 (7) | 0.0021 (6) | −0.0002 (7) |
C8 | 0.0210 (8) | 0.0239 (8) | 0.0095 (9) | 0.0021 (6) | 0.0030 (6) | 0.0028 (6) |
C9 | 0.0167 (7) | 0.0204 (8) | 0.0149 (9) | −0.0010 (6) | 0.0025 (6) | 0.0017 (6) |
C10 | 0.0161 (7) | 0.0196 (7) | 0.0130 (9) | −0.0030 (6) | −0.0007 (6) | −0.0009 (6) |
C11 | 0.0159 (7) | 0.0216 (8) | 0.0163 (9) | 0.0001 (6) | 0.0025 (6) | 0.0005 (6) |
C12 | 0.0204 (7) | 0.0219 (8) | 0.0207 (10) | −0.0012 (6) | −0.0015 (6) | 0.0013 (7) |
C13 | 0.0318 (9) | 0.0316 (9) | 0.0212 (10) | 0.0051 (7) | 0.0022 (7) | 0.0070 (8) |
C14 | 0.0318 (9) | 0.0302 (9) | 0.0280 (12) | 0.0085 (7) | 0.0002 (8) | 0.0036 (8) |
C15 | 0.0156 (7) | 0.0191 (8) | 0.0134 (9) | −0.0003 (6) | −0.0010 (6) | 0.0030 (6) |
C16 | 0.0190 (8) | 0.0264 (8) | 0.0238 (10) | −0.0048 (6) | 0.0043 (7) | 0.0010 (7) |
C17 | 0.0165 (7) | 0.0178 (7) | 0.0191 (10) | −0.0003 (6) | 0.0018 (6) | 0.0013 (6) |
C18 | 0.0178 (8) | 0.0319 (9) | 0.0241 (10) | −0.0055 (7) | 0.0024 (7) | −0.0034 (8) |
C19 | 0.0364 (10) | 0.0282 (9) | 0.0235 (10) | −0.0103 (7) | 0.0004 (8) | −0.0038 (8) |
O1—C1 | 1.211 (2) | C8—C9 | 1.512 (2) |
O2—C2 | 1.217 (2) | C9—C10 | 1.621 (2) |
O3—C9 | 1.4032 (19) | C10—C15 | 1.543 (2) |
O3—H1O3 | 0.86 (2) | C10—C11 | 1.549 (2) |
O4—C15 | 1.3368 (18) | C11—C12 | 1.537 (2) |
O4—C16 | 1.4531 (18) | C11—H11A | 0.9700 |
O5—C15 | 1.201 (2) | C11—H11B | 0.9700 |
O6—C17 | 1.236 (2) | C12—C13 | 1.525 (3) |
N1—C1 | 1.3851 (19) | C12—C14 | 1.527 (2) |
N1—C2 | 1.390 (2) | C12—H12A | 0.9800 |
N1—C19 | 1.467 (2) | C13—H13A | 0.9600 |
N2—C17 | 1.3420 (19) | C13—H13B | 0.9600 |
N2—C10 | 1.4715 (19) | C13—H13C | 0.9600 |
N2—H1N2 | 0.92 (2) | C14—H14A | 0.9600 |
C1—C9 | 1.548 (2) | C14—H14B | 0.9600 |
C2—C3 | 1.486 (2) | C14—H14C | 0.9600 |
C3—C4 | 1.392 (2) | C16—H16A | 0.9600 |
C3—C8 | 1.399 (2) | C16—H16B | 0.9600 |
C4—C5 | 1.386 (3) | C16—H16C | 0.9600 |
C4—H4A | 0.9300 | C17—C18 | 1.504 (2) |
C5—C6 | 1.389 (3) | C18—H18A | 0.9600 |
C5—H5A | 0.9300 | C18—H18B | 0.9600 |
C6—C7 | 1.385 (2) | C18—H18C | 0.9600 |
C6—H6A | 0.9300 | C19—H19A | 0.9600 |
C7—C8 | 1.386 (2) | C19—H19B | 0.9600 |
C7—H7A | 0.9300 | C19—H19C | 0.9600 |
C9—O3—H1O3 | 113.6 (14) | C10—C11—H11A | 108.0 |
C15—O4—C16 | 113.89 (13) | C12—C11—H11B | 108.0 |
C1—N1—C2 | 124.49 (13) | C10—C11—H11B | 108.0 |
C1—N1—C19 | 118.57 (13) | H11A—C11—H11B | 107.2 |
C2—N1—C19 | 116.93 (13) | C13—C12—C14 | 110.13 (14) |
C17—N2—C10 | 126.82 (13) | C13—C12—C11 | 114.00 (13) |
C17—N2—H1N2 | 117.8 (12) | C14—C12—C11 | 108.57 (14) |
C10—N2—H1N2 | 114.8 (12) | C13—C12—H12A | 108.0 |
O1—C1—N1 | 121.72 (14) | C14—C12—H12A | 108.0 |
O1—C1—C9 | 120.54 (14) | C11—C12—H12A | 108.0 |
N1—C1—C9 | 117.67 (13) | C12—C13—H13A | 109.5 |
O2—C2—N1 | 120.25 (15) | C12—C13—H13B | 109.5 |
O2—C2—C3 | 122.84 (15) | H13A—C13—H13B | 109.5 |
N1—C2—C3 | 116.87 (13) | C12—C13—H13C | 109.5 |
C4—C3—C8 | 120.56 (15) | H13A—C13—H13C | 109.5 |
C4—C3—C2 | 118.28 (14) | H13B—C13—H13C | 109.5 |
C8—C3—C2 | 121.12 (14) | C12—C14—H14A | 109.5 |
C5—C4—C3 | 119.65 (16) | C12—C14—H14B | 109.5 |
C5—C4—H4A | 120.2 | H14A—C14—H14B | 109.5 |
C3—C4—H4A | 120.2 | C12—C14—H14C | 109.5 |
C4—C5—C6 | 119.64 (16) | H14A—C14—H14C | 109.5 |
C4—C5—H5A | 120.2 | H14B—C14—H14C | 109.5 |
C6—C5—H5A | 120.2 | O5—C15—O4 | 123.60 (14) |
C7—C6—C5 | 120.92 (16) | O5—C15—C10 | 123.84 (13) |
C7—C6—H6A | 119.5 | O4—C15—C10 | 112.54 (13) |
C5—C6—H6A | 119.5 | O4—C16—H16A | 109.5 |
C6—C7—C8 | 119.87 (15) | O4—C16—H16B | 109.5 |
C6—C7—H7A | 120.1 | H16A—C16—H16B | 109.5 |
C8—C7—H7A | 120.1 | O4—C16—H16C | 109.5 |
C7—C8—C3 | 119.33 (14) | H16A—C16—H16C | 109.5 |
C7—C8—C9 | 121.04 (13) | H16B—C16—H16C | 109.5 |
C3—C8—C9 | 119.57 (14) | O6—C17—N2 | 123.78 (14) |
O3—C9—C8 | 109.28 (12) | O6—C17—C18 | 121.61 (13) |
O3—C9—C1 | 106.64 (13) | N2—C17—C18 | 114.60 (14) |
C8—C9—C1 | 111.74 (12) | C17—C18—H18A | 109.5 |
O3—C9—C10 | 109.99 (12) | C17—C18—H18B | 109.5 |
C8—C9—C10 | 109.67 (13) | H18A—C18—H18B | 109.5 |
C1—C9—C10 | 109.47 (12) | C17—C18—H18C | 109.5 |
N2—C10—C15 | 103.07 (12) | H18A—C18—H18C | 109.5 |
N2—C10—C11 | 112.55 (12) | H18B—C18—H18C | 109.5 |
C15—C10—C11 | 112.23 (12) | N1—C19—H19A | 109.5 |
N2—C10—C9 | 108.76 (12) | N1—C19—H19B | 109.5 |
C15—C10—C9 | 108.54 (11) | H19A—C19—H19B | 109.5 |
C11—C10—C9 | 111.30 (13) | N1—C19—H19C | 109.5 |
C12—C11—C10 | 117.22 (13) | H19A—C19—H19C | 109.5 |
C12—C11—H11A | 108.0 | H19B—C19—H19C | 109.5 |
C2—N1—C1—O1 | 168.38 (15) | O1—C1—C9—C8 | −151.28 (14) |
C19—N1—C1—O1 | −12.6 (2) | N1—C1—C9—C8 | 31.84 (19) |
C2—N1—C1—C9 | −14.8 (2) | O1—C1—C9—C10 | 87.02 (17) |
C19—N1—C1—C9 | 164.27 (14) | N1—C1—C9—C10 | −89.86 (15) |
C1—N1—C2—O2 | 174.17 (15) | C17—N2—C10—C15 | −164.63 (14) |
C19—N1—C2—O2 | −4.9 (2) | C17—N2—C10—C11 | −43.5 (2) |
C1—N1—C2—C3 | −8.2 (2) | C17—N2—C10—C9 | 80.31 (18) |
C19—N1—C2—C3 | 172.78 (14) | O3—C9—C10—N2 | −49.92 (16) |
O2—C2—C3—C4 | 12.4 (2) | C8—C9—C10—N2 | 70.29 (15) |
N1—C2—C3—C4 | −165.20 (15) | C1—C9—C10—N2 | −166.77 (12) |
O2—C2—C3—C8 | −169.92 (15) | O3—C9—C10—C15 | −161.37 (12) |
N1—C2—C3—C8 | 12.5 (2) | C8—C9—C10—C15 | −41.16 (16) |
C8—C3—C4—C5 | −0.9 (2) | C1—C9—C10—C15 | 81.77 (14) |
C2—C3—C4—C5 | 176.79 (16) | O3—C9—C10—C11 | 74.64 (15) |
C3—C4—C5—C6 | −0.5 (3) | C8—C9—C10—C11 | −165.15 (12) |
C4—C5—C6—C7 | 1.0 (3) | C1—C9—C10—C11 | −42.22 (16) |
C5—C6—C7—C8 | 0.0 (3) | N2—C10—C11—C12 | −42.05 (18) |
C6—C7—C8—C3 | −1.4 (2) | C15—C10—C11—C12 | 73.68 (17) |
C6—C7—C8—C9 | 175.79 (15) | C9—C10—C11—C12 | −164.44 (12) |
C4—C3—C8—C7 | 1.9 (2) | C10—C11—C12—C13 | −58.65 (18) |
C2—C3—C8—C7 | −175.74 (15) | C10—C11—C12—C14 | 178.18 (13) |
C4—C3—C8—C9 | −175.38 (15) | C16—O4—C15—O5 | −0.5 (2) |
C2—C3—C8—C9 | 7.0 (2) | C16—O4—C15—C10 | 177.71 (12) |
C7—C8—C9—O3 | 37.1 (2) | N2—C10—C15—O5 | −15.55 (19) |
C3—C8—C9—O3 | −145.72 (14) | C11—C10—C15—O5 | −136.90 (15) |
C7—C8—C9—C1 | 154.86 (15) | C9—C10—C15—O5 | 99.66 (17) |
C3—C8—C9—C1 | −27.9 (2) | N2—C10—C15—O4 | 166.23 (12) |
C7—C8—C9—C10 | −83.55 (17) | C11—C10—C15—O4 | 44.89 (17) |
C3—C8—C9—C10 | 93.64 (17) | C9—C10—C15—O4 | −78.55 (14) |
O1—C1—C9—O3 | −31.9 (2) | C10—N2—C17—O6 | −15.0 (2) |
N1—C1—C9—O3 | 151.20 (13) | C10—N2—C17—C18 | 164.21 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.92 (2) | 2.511 (19) | 3.3431 (17) | 150.3 (15) |
N2—H1N2···O3i | 0.92 (2) | 2.44 (2) | 3.1675 (18) | 135.6 (16) |
O3—H1O3···O6 | 0.86 (2) | 1.83 (2) | 2.6543 (16) | 160 (2) |
C5—H5A···O6ii | 0.93 | 2.59 | 3.469 (2) | 157 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C19H24N2O6 |
Mr | 376.40 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 100 |
a, b, c (Å) | 17.8256 (15), 8.7584 (6), 11.9182 (8) |
β (°) | 100.404 (5) |
V (Å3) | 1830.1 (2) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.85 |
Crystal size (mm) | 0.50 × 0.15 × 0.15 |
Data collection | |
Diffractometer | Bruker APEX DUO CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.678, 0.883 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18268, 2713, 2673 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.586 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.024, 0.059, 1.05 |
No. of reflections | 2713 |
No. of parameters | 257 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.11, −0.14 |
Absolute structure | Flack (1983), 1204 Friedel pairs |
Absolute structure parameter | 0.05 (13) |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H1N2···O1i | 0.92 (2) | 2.511 (19) | 3.3431 (17) | 150.3 (15) |
N2—H1N2···O3i | 0.92 (2) | 2.44 (2) | 3.1675 (18) | 135.6 (16) |
O3—H1O3···O6 | 0.86 (2) | 1.83 (2) | 2.6543 (16) | 160 (2) |
C5—H5A···O6ii | 0.93 | 2.59 | 3.469 (2) | 157 |
Symmetry codes: (i) x, −y+1, z−1/2; (ii) x+1/2, y−1/2, z. |
Acknowledgements
HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the Ministry of Science and Technology of China of the Austria–China Cooperation project (2007DFA41590) is also acknowledged.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Photocycloaddition of isoquinoline-1,3,4-trione combined with following transformation of the photocycloadducts has become facile method to build various scaffold containing an isoquinoline moiety (Yu et al., 2010; Huang et al., 2011). β-Hydroxy-amino acids are important building blocks to constitute more complex natural products. β-Hydroxy tyrosine and β-hydroxy phenylalanine derivatives are found in the clinically important antibiotic glycopeptides vancomycin, β-hydroxy leucine is found in (+)-lactacystin, and E-2-butenyl-4,N-dimethyl-l-threonine is an essential part of cyclosporine (Rao et al., 1995; Nagamitsu et al., 1996; Evans et al., 1986). α,α-Disubstituted amino acids represent a highly interesting class of non-proteinogenic amino acids, especially in view of their potential activity as enzyme inhibitors (Heimgartner, 1991; Rando, 1975). Many bioactive natural products contain β-hydroxy-amino acid or α,α-disubstituted amino acid and there has been intense interest to develop methodology to construct such moieties using photocycloadducts of oxazoles (Griesbeck et al., 2003; Zhang et al., 2004; Wang et al., 2010). The title compound was derived from photocycloadducts of isoquinoline-1,3,4-trione and oxazoles. Due to the importance of β-hydroxy-amino acid derivatives, we report in this paper the crystal structure of the title compound.
In the title racemic compound, Fig. 1, the isoquinoline ring system (N1/C1-C9) is not completely planar, the N-heterocyclic ring (N1/C1-C3/C8/C9) being distorted towards a half-boat conformation with atom C9 deviating by 0.201 (2) Å from the mean plane through the remaining atoms, puckering parameters (Cremer & Pople, 1975) Q = 0.3038 (17) Å, Θ = 70.1 (3)° and ϕ = 110.6 (3)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and comparable to related structures (Fun et al., 2011a,b,c,d). The molecular structure is stabilized by an intramolecular O3–H1O3···O6 hydrogen bond (Table 1) which generates a S(7) ring motif (Fig. 1, Bernstein et al., 1995).
In the crystal structure, Fig. 2, molecules are linked via intermolecular N2–H1N2···O1i, N2–H1N2···O3i and weak C5–H5A···O6ii hydrogen bonds (Table 1) into a three-dimensional network.