5-Meth-oxy-1,2',3-trimethyl-4,6-dioxa-2-aza-spiro-[bicyclo-[3.2.0]hept-2-ene-7,4'-isoquinoline]-1',3'(2'H,4'H)-dione.

In the isoquinoline ring system of the title mol-ecule, C(16)H(16)N(2)O(5), the N-heterocyclic ring is in a half-boat conformation. The dioxaaza-spiro ring is essentially planar [maximum deviation = 0.022 (1) Å] and forms a dihedral angle of 24.56 (4)° with the benzene ring.

Related literature

For general background to and the potential biological activity of the title compound, see: Du et al. (2008 ▶); Chen et al. (2006 ▶); Yu et al. (2010 ▶); Harris et al. (2005 ▶); Zhang et al. (2004 ▶); Wang et al. (2010 ▶); 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 ▶).

Experimental

Crystal data

C16H16N2O5

M = 316.31

Monoclinic,

a = 7.3643 (1) Å

b = 29.8703 (6) Å

c = 6.7802 (1) Å

β = 105.294 (1)°

V = 1438.65 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.46 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.951, T max = 0.971

44501 measured reflections

8265 independent reflections

6842 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.126

S = 1.08

8265 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.37 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/S1600536811016266/lh5241sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016266/lh5241Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016266/lh5241Isup3.cml

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

C16H16N2O5	F(000) = 664
Mr = 316.31	Dx = 1.460 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9541 reflections
a = 7.3643 (1) Å	θ = 2.7–38.9°
b = 29.8703 (6) Å	µ = 0.11 mm−1
c = 6.7802 (1) Å	T = 100 K
β = 105.294 (1)°	Block, colourless
V = 1438.65 (4) Å3	0.46 × 0.31 × 0.27 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	8265 independent reflections
Radiation source: fine-focus sealed tube	6842 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 39.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→11
Tmin = 0.951, Tmax = 0.971	k = −52→52
44501 measured reflections	l = −10→12

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.4048P] where P = (Fo2 + 2Fc2)/3
8265 reflections	(Δ/σ)max = 0.001
212 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.37 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	0.98692 (10)	0.07763 (2)	1.21672 (11)	0.01961 (12)
O2	0.97185 (10)	0.22835 (2)	1.29761 (11)	0.02036 (12)
O3	0.64272 (8)	0.074342 (18)	0.93351 (9)	0.01245 (10)
O4	0.80974 (8)	0.037356 (19)	0.72911 (9)	0.01405 (10)
O5	0.50850 (8)	0.06418 (2)	0.59672 (9)	0.01442 (10)
N1	0.99366 (9)	0.15373 (2)	1.23860 (10)	0.01288 (11)
N2	0.98329 (9)	0.10159 (2)	0.78175 (11)	0.01329 (11)
C1	0.91387 (11)	0.11323 (3)	1.15734 (11)	0.01266 (12)
C2	0.89437 (11)	0.19420 (3)	1.22005 (11)	0.01288 (12)
C3	0.68983 (10)	0.19200 (2)	1.11676 (11)	0.01123 (11)
C4	0.57505 (11)	0.22751 (2)	1.14283 (12)	0.01418 (12)
H4A	0.6279	0.2526	1.2171	0.017*
C5	0.38157 (12)	0.22526 (3)	1.05764 (13)	0.01604 (13)
H5A	0.3048	0.2489	1.0743	0.019*
C6	0.30314 (11)	0.18742 (3)	0.94723 (12)	0.01532 (13)
H6A	0.1739	0.1860	0.8893	0.018*
C7	0.41660 (11)	0.15171 (3)	0.92290 (11)	0.01323 (12)
H7A	0.3630	0.1264	0.8506	0.016*
C8	0.61080 (10)	0.15391 (2)	1.00719 (10)	0.01055 (11)
C9	0.73909 (10)	0.11699 (2)	0.97884 (11)	0.01041 (11)
C10	0.67607 (10)	0.07134 (2)	0.73762 (11)	0.01101 (11)
C11	0.98054 (11)	0.05895 (3)	0.76219 (12)	0.01374 (12)
C12	0.79021 (10)	0.11558 (2)	0.76495 (11)	0.01075 (11)
C13	0.72971 (12)	0.15463 (3)	0.62183 (12)	0.01482 (13)
H13A	0.7495	0.1475	0.4909	0.022*
H13B	0.8025	0.1806	0.6771	0.022*
H13C	0.5986	0.1607	0.6063	0.022*
C14	1.18102 (12)	0.15176 (3)	1.38319 (13)	0.01961 (15)
H14A	1.2585	0.1311	1.3338	0.029*
H14B	1.1695	0.1420	1.5143	0.029*
H14C	1.2376	0.1809	1.3961	0.029*
C15	0.51787 (13)	0.05535 (3)	0.39061 (13)	0.02037 (15)
H15A	0.3927	0.0530	0.3024	0.031*
H15B	0.5840	0.0278	0.3874	0.031*
H15C	0.5831	0.0794	0.3447	0.031*
C16	1.14282 (12)	0.02931 (3)	0.76728 (17)	0.02177 (17)
H16A	1.2575	0.0462	0.8101	0.033*
H16B	1.1314	0.0173	0.6333	0.033*
H16C	1.1448	0.0053	0.8618	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0194 (3)	0.0141 (2)	0.0220 (3)	0.0030 (2)	−0.0004 (2)	0.0036 (2)
O2	0.0186 (3)	0.0147 (3)	0.0249 (3)	−0.0053 (2)	0.0006 (2)	−0.0044 (2)
O3	0.0150 (2)	0.0102 (2)	0.0132 (2)	−0.00369 (17)	0.00555 (17)	−0.00184 (17)
O4	0.0112 (2)	0.0101 (2)	0.0215 (3)	−0.00064 (17)	0.00536 (18)	−0.00282 (18)
O5	0.0113 (2)	0.0169 (2)	0.0144 (2)	−0.00187 (18)	0.00209 (17)	−0.00453 (19)
N1	0.0106 (2)	0.0138 (3)	0.0126 (2)	−0.00073 (19)	0.00022 (18)	−0.0006 (2)
N2	0.0113 (2)	0.0118 (2)	0.0179 (3)	−0.00080 (19)	0.0059 (2)	−0.0016 (2)
C1	0.0126 (3)	0.0126 (3)	0.0121 (3)	0.0000 (2)	0.0022 (2)	0.0005 (2)
C2	0.0132 (3)	0.0125 (3)	0.0123 (3)	−0.0019 (2)	0.0022 (2)	−0.0002 (2)
C3	0.0124 (3)	0.0104 (3)	0.0106 (2)	−0.0008 (2)	0.0026 (2)	0.0001 (2)
C4	0.0174 (3)	0.0106 (3)	0.0146 (3)	0.0006 (2)	0.0044 (2)	−0.0004 (2)
C5	0.0169 (3)	0.0143 (3)	0.0176 (3)	0.0039 (2)	0.0058 (2)	0.0005 (2)
C6	0.0117 (3)	0.0175 (3)	0.0164 (3)	0.0022 (2)	0.0031 (2)	0.0001 (2)
C7	0.0113 (3)	0.0146 (3)	0.0133 (3)	0.0000 (2)	0.0022 (2)	−0.0016 (2)
C8	0.0114 (3)	0.0107 (3)	0.0095 (2)	−0.0003 (2)	0.00277 (19)	−0.0006 (2)
C9	0.0110 (3)	0.0094 (2)	0.0107 (2)	−0.0013 (2)	0.00248 (19)	−0.0008 (2)
C10	0.0104 (3)	0.0102 (3)	0.0127 (3)	−0.0006 (2)	0.0035 (2)	−0.0015 (2)
C11	0.0116 (3)	0.0123 (3)	0.0183 (3)	−0.0008 (2)	0.0056 (2)	−0.0020 (2)
C12	0.0112 (3)	0.0098 (3)	0.0117 (3)	−0.0006 (2)	0.0040 (2)	−0.0009 (2)
C13	0.0187 (3)	0.0124 (3)	0.0145 (3)	0.0010 (2)	0.0064 (2)	0.0021 (2)
C14	0.0131 (3)	0.0241 (4)	0.0178 (3)	−0.0014 (3)	−0.0026 (2)	0.0012 (3)
C15	0.0215 (4)	0.0237 (4)	0.0149 (3)	−0.0007 (3)	0.0030 (3)	−0.0056 (3)
C16	0.0140 (3)	0.0152 (3)	0.0374 (5)	0.0019 (3)	0.0092 (3)	−0.0041 (3)

O1—C1	1.2116 (10)	C6—C7	1.3914 (11)
O2—C2	1.2183 (9)	C6—H6A	0.9300
O3—C10	1.4158 (9)	C7—C8	1.3946 (10)
O3—C9	1.4512 (9)	C7—H7A	0.9300
O4—C11	1.3784 (9)	C8—C9	1.4972 (10)
O4—C10	1.4257 (9)	C9—C12	1.5921 (10)
O5—C10	1.3636 (9)	C10—C12	1.5508 (10)
O5—C15	1.4416 (10)	C11—C16	1.4804 (11)
N1—C1	1.3933 (10)	C12—C13	1.5075 (10)
N1—C2	1.4012 (10)	C13—H13A	0.9600
N1—C14	1.4679 (10)	C13—H13B	0.9600
N2—C11	1.2799 (10)	C13—H13C	0.9600
N2—C12	1.4574 (10)	C14—H14A	0.9600
C1—C9	1.5206 (10)	C14—H14B	0.9600
C2—C3	1.4857 (10)	C14—H14C	0.9600
C3—C4	1.3961 (10)	C15—H15A	0.9600
C3—C8	1.3990 (10)	C15—H15B	0.9600
C4—C5	1.3907 (12)	C15—H15C	0.9600
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.3941 (12)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C10—O3—C9	93.33 (5)	O5—C10—O4	111.53 (6)
C11—O4—C10	105.68 (6)	O3—C10—O4	112.06 (6)
C10—O5—C15	116.23 (6)	O5—C10—C12	125.39 (6)
C1—N1—C2	123.91 (6)	O3—C10—C12	93.25 (5)
C1—N1—C14	116.97 (7)	O4—C10—C12	104.67 (6)
C2—N1—C14	118.08 (7)	N2—C11—O4	118.12 (7)
C11—N2—C12	106.79 (6)	N2—C11—C16	127.02 (7)
O1—C1—N1	121.77 (7)	O4—C11—C16	114.85 (7)
O1—C1—C9	122.53 (7)	N2—C12—C13	112.88 (6)
N1—C1—C9	115.52 (6)	N2—C12—C10	104.58 (6)
O2—C2—N1	120.65 (7)	C13—C12—C10	121.57 (6)
O2—C2—C3	122.79 (7)	N2—C12—C9	113.37 (6)
N1—C2—C3	116.38 (6)	C13—C12—C9	117.72 (6)
C4—C3—C8	120.27 (7)	C10—C12—C9	83.13 (5)
C4—C3—C2	118.63 (7)	C12—C13—H13A	109.5
C8—C3—C2	120.95 (6)	C12—C13—H13B	109.5
C5—C4—C3	119.93 (7)	H13A—C13—H13B	109.5
C5—C4—H4A	120.0	C12—C13—H13C	109.5
C3—C4—H4A	120.0	H13A—C13—H13C	109.5
C4—C5—C6	119.74 (7)	H13B—C13—H13C	109.5
C4—C5—H5A	120.1	N1—C14—H14A	109.5
C6—C5—H5A	120.1	N1—C14—H14B	109.5
C7—C6—C5	120.57 (7)	H14A—C14—H14B	109.5
C7—C6—H6A	119.7	N1—C14—H14C	109.5
C5—C6—H6A	119.7	H14A—C14—H14C	109.5
C6—C7—C8	119.88 (7)	H14B—C14—H14C	109.5
C6—C7—H7A	120.1	O5—C15—H15A	109.5
C8—C7—H7A	120.1	O5—C15—H15B	109.5
C7—C8—C3	119.60 (7)	H15A—C15—H15B	109.5
C7—C8—C9	121.75 (6)	O5—C15—H15C	109.5
C3—C8—C9	118.62 (6)	H15A—C15—H15C	109.5
O3—C9—C8	112.58 (6)	H15B—C15—H15C	109.5
O3—C9—C1	111.58 (6)	C11—C16—H16A	109.5
C8—C9—C1	112.49 (6)	C11—C16—H16B	109.5
O3—C9—C12	90.22 (5)	H16A—C16—H16B	109.5
C8—C9—C12	116.44 (6)	C11—C16—H16C	109.5
C1—C9—C12	111.66 (6)	H16A—C16—H16C	109.5
O5—C10—O3	108.56 (6)	H16B—C16—H16C	109.5
C2—N1—C1—O1	−161.40 (8)	O1—C1—C9—C12	−81.94 (9)
C14—N1—C1—O1	6.68 (11)	N1—C1—C9—C12	93.26 (7)
C2—N1—C1—C9	23.35 (10)	C15—O5—C10—O3	−173.45 (6)
C14—N1—C1—C9	−168.56 (7)	C15—O5—C10—O4	−49.51 (9)
C1—N1—C2—O2	178.82 (8)	C15—O5—C10—C12	78.38 (9)
C14—N1—C2—O2	10.86 (11)	C9—O3—C10—O5	−126.97 (6)
C1—N1—C2—C3	3.52 (10)	C9—O3—C10—O4	109.41 (6)
C14—N1—C2—C3	−164.44 (7)	C9—O3—C10—C12	2.15 (6)
O2—C2—C3—C4	−12.66 (11)	C11—O4—C10—O5	142.09 (6)
N1—C2—C3—C4	162.54 (7)	C11—O4—C10—O3	−95.97 (7)
O2—C2—C3—C8	171.75 (7)	C11—O4—C10—C12	3.77 (7)
N1—C2—C3—C8	−13.05 (10)	C12—N2—C11—O4	0.91 (9)
C8—C3—C4—C5	−0.74 (11)	C12—N2—C11—C16	179.69 (8)
C2—C3—C4—C5	−176.36 (7)	C10—O4—C11—N2	−3.21 (9)
C3—C4—C5—C6	0.27 (12)	C10—O4—C11—C16	177.86 (7)
C4—C5—C6—C7	0.53 (12)	C11—N2—C12—C13	−132.59 (7)
C5—C6—C7—C8	−0.85 (12)	C11—N2—C12—C10	1.60 (8)
C6—C7—C8—C3	0.38 (11)	C11—N2—C12—C9	90.33 (7)
C6—C7—C8—C9	−177.87 (7)	O5—C10—C12—N2	−133.99 (7)
C4—C3—C8—C7	0.41 (10)	O3—C10—C12—N2	110.46 (6)
C2—C3—C8—C7	175.93 (7)	O4—C10—C12—N2	−3.35 (7)
C4—C3—C8—C9	178.71 (7)	O5—C10—C12—C13	−4.83 (10)
C2—C3—C8—C9	−5.77 (10)	O3—C10—C12—C13	−120.39 (7)
C10—O3—C9—C8	116.84 (6)	O4—C10—C12—C13	125.81 (7)
C10—O3—C9—C1	−115.57 (6)	O5—C10—C12—C9	113.59 (7)
C10—O3—C9—C12	−2.09 (5)	O3—C10—C12—C9	−1.97 (5)
C7—C8—C9—O3	−23.21 (9)	O4—C10—C12—C9	−115.78 (6)
C3—C8—C9—O3	158.52 (6)	O3—C9—C12—N2	−101.04 (6)
C7—C8—C9—C1	−150.32 (7)	C8—C9—C12—N2	143.45 (6)
C3—C8—C9—C1	31.42 (9)	C1—C9—C12—N2	12.37 (8)
C7—C8—C9—C12	78.99 (8)	O3—C9—C12—C13	124.09 (7)
C3—C8—C9—C12	−99.28 (7)	C8—C9—C12—C13	8.58 (9)
O1—C1—C9—O3	17.35 (10)	C1—C9—C12—C13	−122.51 (7)
N1—C1—C9—O3	−167.44 (6)	O3—C9—C12—C10	1.92 (5)
O1—C1—C9—C8	144.99 (8)	C8—C9—C12—C10	−113.59 (6)
N1—C1—C9—C8	−39.81 (9)	C1—C9—C12—C10	115.32 (6)