Methyl 4'-isobutyl-2,2'-dimethyl-1,3-dioxo-2,3-dihydro-1H,4'H-spiro-[iso-quinoline-4,5'-oxazole]-4'-carboxyl-ate.

In the isoquinoline ring system of the title mol-ecule, C(19)H(22)N(2)O(5), the N-heterocyclic ring is in a half-boat conformation. The dioxa-2-aza-spiro ring is essentially planar [maximum deviation = 0.042 (1) Å] and forms a dihedral angle of 81.85 (4)° with the benzene ring. In the crystal, the mol-ecules are linked via inter-molecular C-H⋯O hydrogen bonds into chains along [010].

Related literature

For general background to and the potential biological activity of the title compound, see: Pollers-Wieers et al. (1981 ▶); Malamas et al. (1994 ▶); Yu et al. (2010 ▶); Mitchell et al. (1995 ▶, 2000 ▶); Badillo et al. (2010 ▶); Wang et al. (2010 ▶); Nair et al. (2002 ▶); Huang et al. (2011 ▶). 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 ▶).

Experimental

Crystal data

C19H22N2O5

M = 358.39

Triclinic,

a = 8.6764 (1) Å

b = 8.9366 (1) Å

c = 12.0684 (2) Å

α = 93.495 (1)°

β = 109.892 (1)°

γ = 98.426 (1)°

V = 864.22 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.40 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.961, T max = 0.982

25638 measured reflections

6231 independent reflections

5381 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.113

S = 1.05

6231 reflections

240 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.24 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/S1600536811019003/rz2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019003/rz2597Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019003/rz2597Isup3.cml

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

C19H22N2O5	Z = 2
Mr = 358.39	F(000) = 380
Triclinic, P1	Dx = 1.377 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6764 (1) Å	Cell parameters from 9993 reflections
b = 8.9366 (1) Å	θ = 2.3–35.1°
c = 12.0684 (2) Å	µ = 0.10 mm−1
α = 93.495 (1)°	T = 100 K
β = 109.892 (1)°	Block, colourless
γ = 98.426 (1)°	0.40 × 0.29 × 0.18 mm
V = 864.22 (2) Å3

Bruker SMART APEXII CCD area-detector diffractometer	6231 independent reflections
Radiation source: fine-focus sealed tube	5381 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 32.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.961, Tmax = 0.982	k = −13→13
25638 measured reflections	l = −16→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.1577P] where P = (Fo2 + 2Fc2)/3
6231 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.24 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
O1	0.56369 (10)	−0.13923 (8)	0.36689 (7)	0.02808 (16)
O2	0.61673 (8)	0.30662 (7)	0.21139 (6)	0.01906 (13)
O3	0.70178 (7)	0.17637 (7)	0.03819 (5)	0.01584 (12)
O4	1.13223 (8)	0.01941 (7)	0.19476 (6)	0.02001 (13)
O5	1.02241 (8)	0.00373 (7)	0.33903 (6)	0.01843 (13)
N1	0.60176 (9)	0.08767 (8)	0.29574 (6)	0.01547 (13)
N2	0.98015 (8)	0.26379 (8)	0.11623 (6)	0.01398 (13)
C1	0.71382 (9)	−0.05589 (9)	0.12763 (7)	0.01375 (14)
C2	0.75196 (10)	−0.12948 (9)	0.03755 (7)	0.01669 (15)
H2A	0.7913	−0.0729	−0.0126	0.020*
C3	0.73110 (11)	−0.28759 (10)	0.02283 (8)	0.01903 (16)
H3A	0.7556	−0.3364	−0.0378	0.023*
C4	0.67396 (11)	−0.37359 (10)	0.09800 (8)	0.01860 (16)
H4A	0.6621	−0.4792	0.0884	0.022*
C5	0.63485 (10)	−0.30090 (9)	0.18736 (7)	0.01695 (15)
H5A	0.5961	−0.3578	0.2376	0.020*
C6	0.65376 (10)	−0.14210 (9)	0.20173 (7)	0.01444 (14)
C7	0.60524 (10)	−0.06867 (10)	0.29540 (7)	0.01696 (15)
C8	0.64684 (9)	0.17845 (9)	0.21858 (7)	0.01427 (14)
C9	0.74719 (9)	0.11548 (9)	0.15004 (7)	0.01297 (13)
C10	0.94372 (9)	0.18962 (9)	0.21130 (7)	0.01221 (13)
C11	0.84438 (10)	0.25402 (9)	0.02944 (7)	0.01396 (14)
C12	0.81958 (11)	0.31809 (10)	−0.08488 (7)	0.01760 (15)
H12A	0.9226	0.3774	−0.0823	0.026*
H12B	0.7366	0.3818	−0.0976	0.026*
H12C	0.7834	0.2365	−0.1486	0.026*
C13	0.98781 (9)	0.30600 (9)	0.32243 (7)	0.01391 (14)
H13A	0.9391	0.3950	0.2979	0.017*
H13B	0.9362	0.2612	0.3753	0.017*
C14	1.17540 (9)	0.35881 (9)	0.39278 (7)	0.01424 (14)
H14A	1.2278	0.2682	0.4053	0.017*
C15	1.19883 (11)	0.43954 (11)	0.51412 (8)	0.02220 (17)
H15A	1.3156	0.4677	0.5597	0.033*
H15B	1.1464	0.3723	0.5551	0.033*
H15C	1.1492	0.5293	0.5039	0.033*
C16	1.26352 (11)	0.46363 (11)	0.32908 (8)	0.02157 (17)
H16A	1.3776	0.4980	0.3794	0.032*
H16B	1.2091	0.5499	0.3110	0.032*
H16C	1.2593	0.4089	0.2568	0.032*
C17	1.04488 (9)	0.06210 (9)	0.24456 (7)	0.01415 (14)
C18	1.10003 (13)	−0.12653 (12)	0.37361 (10)	0.0282 (2)
H18A	1.0943	−0.1492	0.4490	0.042*
H18B	1.2145	−0.1044	0.3798	0.042*
H18C	1.0429	−0.2127	0.3151	0.042*
C19	0.52591 (11)	0.15905 (10)	0.37250 (8)	0.02020 (16)
H19A	0.6016	0.2477	0.4198	0.030*
H19B	0.5024	0.0878	0.4235	0.030*
H19C	0.4243	0.1883	0.3243	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0440 (4)	0.0228 (3)	0.0276 (4)	0.0051 (3)	0.0250 (3)	0.0085 (3)
O2	0.0179 (3)	0.0170 (3)	0.0230 (3)	0.0048 (2)	0.0072 (2)	0.0034 (2)
O3	0.0145 (2)	0.0189 (3)	0.0129 (2)	0.0007 (2)	0.0035 (2)	0.0058 (2)
O4	0.0199 (3)	0.0196 (3)	0.0222 (3)	0.0068 (2)	0.0083 (2)	0.0017 (2)
O5	0.0200 (3)	0.0176 (3)	0.0172 (3)	0.0030 (2)	0.0053 (2)	0.0072 (2)
N1	0.0155 (3)	0.0164 (3)	0.0166 (3)	0.0018 (2)	0.0087 (2)	0.0016 (2)
N2	0.0163 (3)	0.0142 (3)	0.0129 (3)	0.0018 (2)	0.0071 (2)	0.0031 (2)
C1	0.0132 (3)	0.0142 (3)	0.0124 (3)	0.0001 (2)	0.0037 (2)	0.0014 (2)
C2	0.0182 (3)	0.0171 (3)	0.0141 (3)	−0.0007 (3)	0.0067 (3)	0.0000 (3)
C3	0.0200 (4)	0.0180 (4)	0.0177 (4)	0.0003 (3)	0.0070 (3)	−0.0026 (3)
C4	0.0186 (4)	0.0141 (3)	0.0204 (4)	0.0007 (3)	0.0047 (3)	0.0002 (3)
C5	0.0171 (3)	0.0153 (3)	0.0170 (3)	0.0005 (3)	0.0048 (3)	0.0039 (3)
C6	0.0141 (3)	0.0152 (3)	0.0133 (3)	0.0007 (3)	0.0045 (3)	0.0021 (3)
C7	0.0185 (3)	0.0176 (4)	0.0161 (3)	0.0015 (3)	0.0083 (3)	0.0031 (3)
C8	0.0115 (3)	0.0163 (3)	0.0144 (3)	0.0009 (2)	0.0044 (2)	0.0022 (3)
C9	0.0130 (3)	0.0140 (3)	0.0115 (3)	0.0010 (2)	0.0042 (2)	0.0030 (2)
C10	0.0122 (3)	0.0130 (3)	0.0117 (3)	0.0016 (2)	0.0048 (2)	0.0021 (2)
C11	0.0173 (3)	0.0121 (3)	0.0136 (3)	0.0020 (3)	0.0071 (3)	0.0022 (2)
C12	0.0227 (4)	0.0172 (3)	0.0137 (3)	0.0033 (3)	0.0070 (3)	0.0048 (3)
C13	0.0127 (3)	0.0157 (3)	0.0129 (3)	0.0015 (2)	0.0048 (2)	−0.0007 (3)
C14	0.0126 (3)	0.0153 (3)	0.0140 (3)	0.0012 (2)	0.0044 (2)	0.0002 (3)
C15	0.0170 (4)	0.0295 (4)	0.0163 (4)	−0.0015 (3)	0.0046 (3)	−0.0045 (3)
C16	0.0175 (4)	0.0252 (4)	0.0199 (4)	−0.0029 (3)	0.0065 (3)	0.0034 (3)
C17	0.0137 (3)	0.0130 (3)	0.0135 (3)	0.0005 (2)	0.0028 (3)	0.0014 (2)
C18	0.0264 (4)	0.0233 (4)	0.0332 (5)	0.0066 (4)	0.0054 (4)	0.0157 (4)
C19	0.0194 (4)	0.0222 (4)	0.0224 (4)	0.0029 (3)	0.0126 (3)	−0.0004 (3)

O1—C7	1.2178 (10)	C9—C10	1.6262 (11)
O2—C8	1.2133 (10)	C10—C17	1.5295 (11)
O3—C11	1.3675 (10)	C10—C13	1.5462 (11)
O3—C9	1.4365 (9)	C11—C12	1.4859 (11)
O4—C17	1.2033 (10)	C12—H12A	0.9600
O5—C17	1.3431 (10)	C12—H12B	0.9600
O5—C18	1.4424 (11)	C12—H12C	0.9600
N1—C8	1.3875 (10)	C13—C14	1.5422 (11)
N1—C7	1.4016 (11)	C13—H13A	0.9700
N1—C19	1.4711 (11)	C13—H13B	0.9700
N2—C11	1.2694 (10)	C14—C16	1.5268 (12)
N2—C10	1.4608 (10)	C14—C15	1.5270 (12)
C1—C2	1.3948 (11)	C14—H14A	0.9800
C1—C6	1.3958 (11)	C15—H15A	0.9600
C1—C9	1.5062 (11)	C15—H15B	0.9600
C2—C3	1.3904 (12)	C15—H15C	0.9600
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.3925 (12)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
C4—C5	1.3886 (12)	C18—H18A	0.9600
C4—H4A	0.9300	C18—H18B	0.9600
C5—C6	1.3976 (11)	C18—H18C	0.9600
C5—H5A	0.9300	C19—H19A	0.9600
C6—C7	1.4833 (12)	C19—H19B	0.9600
C8—C9	1.5284 (11)	C19—H19C	0.9600
C11—O3—C9	107.44 (6)	C11—C12—H12A	109.5
C17—O5—C18	115.39 (7)	C11—C12—H12B	109.5
C8—N1—C7	124.82 (7)	H12A—C12—H12B	109.5
C8—N1—C19	116.23 (7)	C11—C12—H12C	109.5
C7—N1—C19	118.50 (7)	H12A—C12—H12C	109.5
C11—N2—C10	108.20 (6)	H12B—C12—H12C	109.5
C2—C1—C6	119.53 (7)	C14—C13—C10	115.65 (6)
C2—C1—C9	120.39 (7)	C14—C13—H13A	108.4
C6—C1—C9	119.97 (7)	C10—C13—H13A	108.4
C3—C2—C1	119.87 (8)	C14—C13—H13B	108.4
C3—C2—H2A	120.1	C10—C13—H13B	108.4
C1—C2—H2A	120.1	H13A—C13—H13B	107.4
C2—C3—C4	120.66 (8)	C16—C14—C15	109.57 (7)
C2—C3—H3A	119.7	C16—C14—C13	113.42 (7)
C4—C3—H3A	119.7	C15—C14—C13	109.33 (7)
C5—C4—C3	119.68 (8)	C16—C14—H14A	108.1
C5—C4—H4A	120.2	C15—C14—H14A	108.1
C3—C4—H4A	120.2	C13—C14—H14A	108.1
C4—C5—C6	119.92 (8)	C14—C15—H15A	109.5
C4—C5—H5A	120.0	C14—C15—H15B	109.5
C6—C5—H5A	120.0	H15A—C15—H15B	109.5
C1—C6—C5	120.33 (8)	C14—C15—H15C	109.5
C1—C6—C7	121.22 (7)	H15A—C15—H15C	109.5
C5—C6—C7	118.43 (7)	H15B—C15—H15C	109.5
O1—C7—N1	120.23 (8)	C14—C16—H16A	109.5
O1—C7—C6	122.86 (8)	C14—C16—H16B	109.5
N1—C7—C6	116.85 (7)	H16A—C16—H16B	109.5
O2—C8—N1	121.17 (8)	C14—C16—H16C	109.5
O2—C8—C9	121.21 (7)	H16A—C16—H16C	109.5
N1—C8—C9	117.46 (7)	H16B—C16—H16C	109.5
O3—C9—C1	109.04 (6)	O4—C17—O5	124.41 (7)
O3—C9—C8	106.82 (6)	O4—C17—C10	125.85 (7)
C1—C9—C8	113.48 (6)	O5—C17—C10	109.73 (7)
O3—C9—C10	102.23 (6)	O5—C18—H18A	109.5
C1—C9—C10	113.79 (6)	O5—C18—H18B	109.5
C8—C9—C10	110.63 (6)	H18A—C18—H18B	109.5
N2—C10—C17	110.09 (6)	O5—C18—H18C	109.5
N2—C10—C13	110.48 (6)	H18A—C18—H18C	109.5
C17—C10—C13	108.90 (6)	H18B—C18—H18C	109.5
N2—C10—C9	103.04 (6)	N1—C19—H19A	109.5
C17—C10—C9	109.24 (6)	N1—C19—H19B	109.5
C13—C10—C9	114.95 (6)	H19A—C19—H19B	109.5
N2—C11—O3	118.54 (7)	N1—C19—H19C	109.5
N2—C11—C12	127.35 (7)	H19A—C19—H19C	109.5
O3—C11—C12	114.11 (7)	H19B—C19—H19C	109.5
C6—C1—C2—C3	−0.47 (12)	O2—C8—C9—C1	−156.00 (7)
C9—C1—C2—C3	175.68 (7)	N1—C8—C9—C1	28.49 (9)
C1—C2—C3—C4	−0.65 (13)	O2—C8—C9—C10	74.70 (9)
C2—C3—C4—C5	1.05 (13)	N1—C8—C9—C10	−100.81 (8)
C3—C4—C5—C6	−0.31 (12)	C11—N2—C10—C17	122.44 (7)
C2—C1—C6—C5	1.20 (12)	C11—N2—C10—C13	−117.25 (7)
C9—C1—C6—C5	−174.97 (7)	C11—N2—C10—C9	6.03 (8)
C2—C1—C6—C7	−177.48 (7)	O3—C9—C10—N2	−7.21 (7)
C9—C1—C6—C7	6.35 (11)	C1—C9—C10—N2	110.20 (7)
C4—C5—C6—C1	−0.81 (12)	C8—C9—C10—N2	−120.67 (7)
C4—C5—C6—C7	177.91 (7)	O3—C9—C10—C17	−124.22 (6)
C8—N1—C7—O1	179.82 (8)	C1—C9—C10—C17	−6.82 (9)
C19—N1—C7—O1	−8.22 (12)	C8—C9—C10—C17	122.32 (7)
C8—N1—C7—C6	−2.85 (12)	O3—C9—C10—C13	113.04 (7)
C19—N1—C7—C6	169.11 (7)	C1—C9—C10—C13	−129.55 (7)
C1—C6—C7—O1	−174.64 (8)	C8—C9—C10—C13	−0.41 (9)
C5—C6—C7—O1	6.66 (13)	C10—N2—C11—O3	−2.63 (10)
C1—C6—C7—N1	8.11 (11)	C10—N2—C11—C12	177.58 (8)
C5—C6—C7—N1	−170.60 (7)	C9—O3—C11—N2	−2.67 (10)
C7—N1—C8—O2	168.43 (8)	C9—O3—C11—C12	177.15 (7)
C19—N1—C8—O2	−3.69 (11)	N2—C10—C13—C14	−72.97 (8)
C7—N1—C8—C9	−16.05 (11)	C17—C10—C13—C14	48.05 (9)
C19—N1—C8—C9	171.82 (7)	C9—C10—C13—C14	170.96 (6)
C11—O3—C9—C1	−114.79 (7)	C10—C13—C14—C16	71.60 (9)
C11—O3—C9—C8	122.21 (7)	C10—C13—C14—C15	−165.79 (7)
C11—O3—C9—C10	5.96 (8)	C18—O5—C17—O4	−5.16 (12)
C2—C1—C9—O3	40.97 (9)	C18—O5—C17—C10	174.99 (7)
C6—C1—C9—O3	−142.90 (7)	N2—C10—C17—O4	−5.43 (11)
C2—C1—C9—C8	159.89 (7)	C13—C10—C17—O4	−126.69 (8)
C6—C1—C9—C8	−23.97 (10)	C9—C10—C17—O4	107.03 (9)
C2—C1—C9—C10	−72.42 (9)	N2—C10—C17—O5	174.42 (6)
C6—C1—C9—C10	103.71 (8)	C13—C10—C17—O5	53.16 (8)
O2—C8—C9—O3	−35.81 (10)	C9—C10—C17—O5	−73.12 (8)
N1—C8—C9—O3	148.68 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4i	0.93	2.56	3.4353 (11)	158
C4—H4A···O2ii	0.93	2.56	3.2878 (11)	136
C12—H12C···O4i	0.96	2.59	3.3600 (11)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4i	0.93	2.56	3.4353 (11)	158
C4—H4A⋯O2ii	0.93	2.56	3.2878 (11)	136
C12—H12C⋯O4i	0.96	2.59	3.3600 (11)	138

Symmetry codes: (i) ; (ii) .