6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-aza­bicyclo­[3.3.1]nonane-7-carboxyl­ate

Xu, S.; Wang, C.; Liu, J.; Liu, X.; Li, L.

doi:10.1107/S1600536809054786

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o245

doi:10.1107/S1600536809054786

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6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-azabicyclo[3.3.1]nonane-7-carboxylate

Sheng-guang Xu,^a ^* Chun-hua Wang,^a Jun-shen Liu,^a Xi-guang Liu ^a and Long Li ^a

^aSchool of Chemistry & Materials Science, Ludong University, Yantai of Shandong, People's Republic of China
^*Correspondence e-mail: xushengguangldu@yahoo.cn

(Received 5 December 2009; accepted 20 December 2009; online 24 December 2009)

In the title compound, C₂₃H₂₃NO₅, the C₅N ring adopts an envelope conformation with a C atom as the flap, whilst the saturated C₆ ring fused to it adopts a chair conformation. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R₂²(8) loops.

Related literature

For further information on the title compound as a building block in a dynamic combinatorial library, see: Xu & Giuseppone (2008 ). For further synthetic details, see: Askew et al. (1989 ); Rebek et al. (1987 ); Steglich & Höfle (1969 ); Williams et al. (1989 ); Chamontin et al. (1999 ).

Experimental

Crystal data

C₂₃H₂₃NO₅
M_r = 393.42
Monoclinic, P 2₁ /c
a = 11.896 (2) Å
b = 11.692 (2) Å
c = 16.636 (2) Å
β = 121.124 (9)°
V = 1980.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.28 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.974, T_max = 0.982
10443 measured reflections
3897 independent reflections
3217 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.03
3897 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H22⋯O5ⁱ	0.87	2.02	2.8776 (14)	166
Symmetry code: (i) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809054786/hb5273sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809054786/hb5273Isup2.hkl

checkCIF report

Comment top

The title compound (6-formylnaphthalen-2-yl cis-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo[3.3.1]nonane-7-carboxylate), reported by Xu and Giuseppone (Xu et al., 2008) as a key building block in a dynamic combinatorial library in which one product was self-amplified via self-complementary process, contains a steric bulk and a imide functional group which is a good receptor for adenine through the hydrogen bonding interaction like a base pairing. Herein we report the molecular and crystal structure of the title compound.

The unit structure of the title compound is illustrated in Fig. 1. The asymmetry of the title compound contains two ten-member rings: a naphthalene ring and a V conformation ring, which are connected each other via the carboxylate (O₂—C₁₂—O₃). The naphth ring is approximately planar. In addition, the molecures are linked by the N₁—H···O₅ hrdrogen bond, forming inversion dimers.

Related literature top

For further information on the title compound as a building block in a dynamic combinatorial library, see: Xu & Giuseppone (2008). For further synthetic details, see: Askew et al. (1989); Rebek et al. (1987); Steglich & Höfle (1969); Williams et al. (1989); Chamontin et al. (1999).

Experimental top

As delineated in Scheme 1, the product was synthesized (Rebek et al., 1987; Askew et al., 1989; Williams et al., 1989) from the starting material Kemp's triacid (01) which is commercially available. Firstly, anhydride acid (02) was prepared after dehydration of Kemp Triacid (01) under reflux 17 h in xylenes under N₂. After anhydride acid (02) was treated with concentrated aqueous ammonium hydroxide (NH₄OH) and 4-(dimthylamino)pyridine (DMAP) (Steglich et al., 1969) at 383 K overnight, Imide Acid (03) was gained. Then we got Imide Acid Chloride (04) after the solution of Imide Acid (03) in fresh thionylchloride was reflux under nitrogen atmosphere for 3 h. At the end the target Materiel Al₁ was prepared from Imide Acid Chloride (04) reacted with 6-hydroxy-2-naphthaldehyde (Chamontin et al., 1999) catalyzed by sodium hydride (NaH).

Product, yielding 60%. ¹H NMR (400MH_z,CDCl₃, TMS) δ 10.069 (s, 1H), δ 8.244 (s, 1H), δ 7.930–7.818 (m, 3H), δ 7.589 (s, 1H), δ 7.589 (s, 1H), δ 7.540–7.535 (d, 1H), δ 7.234–7.206 (m, 1H), δ 2.822–2.787 (d, 2H), δ 2.029–1.996 (d, 1H), δ 1.488–1.267 (m, 12H); ¹³C NMR (CDCl₃) δ 191.97, 176.06, 173.75,150.71, 137.03, 134.04, 133.97, 131.06, 130.68, 128.88, 123.60, 122.10, 118.76,44.329, 43.799, 42.625, 40.178, 30.529, 24.313; ESI-TOF Eaxct Mass for C₂₃H₂₃NO₅[M+Li]⁺: calcd 399.1722, 400.1731, 401.1764, 402.1791, found 399.1740, 400.1769, 401.1801, 402.1832.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Displacement ellipsoid plot (50% probability level) of (I).
	Fig. 2. The packing diagram of (I) (viewed down the b axis)
	Fig. 3. The formation of the title compound.

6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-azabicyclo[3.3.1]nonane-7-carboxylate top

Crystal data top

C₂₃H₂₃NO₅	F(000) = 832
M_r = 393.42	D_x = 1.319 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4643 reflections
a = 11.896 (2) Å	θ = 2.5–27.6°
b = 11.692 (2) Å	µ = 0.09 mm⁻¹
c = 16.636 (2) Å	T = 298 K
β = 121.124 (9)°	Block, colourless
V = 1980.8 (5) Å³	0.28 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3897 independent reflections
Radiation source: fine-focus sealed tube	3217 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scan	θ_max = 26.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→14
T_min = 0.974, T_max = 0.982	k = −14→14
10443 measured reflections	l = −20→20

Refinement top

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0518P)² + 0.4083P] where P = (F_o² + 2F_c²)/3
3897 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₃H₂₃NO₅	V = 1980.8 (5) Å³
M_r = 393.42	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.896 (2) Å	µ = 0.09 mm⁻¹
b = 11.692 (2) Å	T = 298 K
c = 16.636 (2) Å	0.28 × 0.20 × 0.20 mm
β = 121.124 (9)°

Data collection top

Bruker APEXII CCD diffractometer	3897 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3217 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.982	R_int = 0.018
10443 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
3897 reflections	Δρ_min = −0.22 e Å⁻³
265 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
O1	1.13914 (15)	1.52850 (10)	0.66763 (9)	0.0827 (4)
O2	0.79931 (9)	0.84989 (8)	0.48814 (7)	0.0446 (2)
O3	0.71422 (10)	0.81424 (10)	0.57896 (7)	0.0535 (3)
O4	0.56292 (11)	0.98673 (8)	0.30018 (7)	0.0501 (3)
O5	0.40949 (11)	0.87877 (9)	0.48523 (8)	0.0535 (3)
N1	0.48608 (11)	0.92723 (9)	0.39106 (8)	0.0393 (3)
H22	0.5094	0.9926	0.4202	0.047*
C1	1.14643 (17)	1.43589 (14)	0.70153 (12)	0.0571 (4)
H1	1.2061	1.4268	0.7654	0.069*
C2	1.06708 (14)	1.33579 (12)	0.64863 (10)	0.0419 (3)
C3	1.08892 (14)	1.23220 (12)	0.69289 (10)	0.0434 (3)
H3	1.1515	1.2268	0.7566	0.052*
C4	1.01832 (12)	1.13362 (11)	0.64376 (9)	0.0382 (3)
C5	0.92258 (12)	1.14345 (11)	0.54671 (9)	0.0354 (3)
C6	0.90366 (13)	1.25141 (12)	0.50278 (10)	0.0434 (3)
H6	0.8427	1.2584	0.4389	0.052*
C7	0.97267 (14)	1.34465 (12)	0.55196 (10)	0.0442 (3)
H7	0.9577	1.4149	0.5218	0.053*
C8	0.84911 (12)	1.04604 (12)	0.49738 (9)	0.0393 (3)
H8	0.7853	1.0515	0.4340	0.047*
C9	0.87159 (13)	0.94461 (12)	0.54251 (9)	0.0393 (3)
C10	0.96829 (15)	0.93151 (13)	0.63736 (10)	0.0500 (4)
H10	0.9842	0.8604	0.6663	0.060*
C11	1.03874 (15)	1.02504 (13)	0.68656 (10)	0.0509 (4)
H11	1.1019	1.0172	0.7499	0.061*
C12	0.72086 (12)	0.79239 (11)	0.51122 (9)	0.0363 (3)
C13	0.65192 (13)	0.69261 (10)	0.44424 (9)	0.0362 (3)
C14	0.75342 (16)	0.59438 (13)	0.48707 (12)	0.0572 (4)
H14A	0.7185	0.5273	0.4486	0.086*
H14B	0.7718	0.5780	0.5493	0.086*
H14C	0.8330	0.6169	0.4899	0.086*
C15	0.61823 (13)	0.71551 (11)	0.34325 (9)	0.0369 (3)
H15A	0.6067	0.6425	0.3123	0.044*
H15B	0.6928	0.7532	0.3459	0.044*
C16	0.49451 (13)	0.78899 (10)	0.28177 (8)	0.0359 (3)
C17	0.37796 (13)	0.73661 (11)	0.28312 (9)	0.0382 (3)
H17A	0.3616	0.6602	0.2567	0.046*
H17B	0.3001	0.7824	0.2447	0.046*
C18	0.40466 (13)	0.73080 (10)	0.38319 (9)	0.0360 (3)
C19	0.52754 (13)	0.65756 (11)	0.44435 (9)	0.0389 (3)
H19A	0.5468	0.6601	0.5085	0.047*
H19B	0.5071	0.5789	0.4233	0.047*
C20	0.51756 (13)	0.90892 (10)	0.32291 (8)	0.0358 (3)
C21	0.43114 (13)	0.85050 (11)	0.42433 (9)	0.0374 (3)
C22	0.47044 (18)	0.79546 (14)	0.18231 (10)	0.0546 (4)
H22A	0.3959	0.8434	0.1443	0.082*
H22B	0.4539	0.7201	0.1557	0.082*
H22C	0.5465	0.8269	0.1844	0.082*
C23	0.28802 (16)	0.68016 (14)	0.38570 (12)	0.0558 (4)
H23A	0.3061	0.6813	0.4490	0.084*
H23B	0.2740	0.6027	0.3633	0.084*
H23C	0.2108	0.7247	0.3463	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1151 (11)	0.0470 (7)	0.0734 (9)	−0.0257 (7)	0.0398 (8)	−0.0030 (6)
O2	0.0485 (6)	0.0427 (5)	0.0449 (5)	−0.0134 (4)	0.0257 (5)	−0.0075 (4)
O3	0.0559 (6)	0.0680 (7)	0.0351 (5)	−0.0186 (5)	0.0224 (5)	−0.0079 (5)
O4	0.0676 (7)	0.0338 (5)	0.0467 (6)	−0.0063 (5)	0.0280 (5)	0.0051 (4)
O5	0.0652 (7)	0.0502 (6)	0.0614 (7)	−0.0137 (5)	0.0441 (6)	−0.0232 (5)
N1	0.0515 (7)	0.0253 (5)	0.0403 (6)	−0.0041 (5)	0.0232 (5)	−0.0089 (4)
C1	0.0697 (10)	0.0489 (9)	0.0525 (9)	−0.0152 (8)	0.0315 (8)	−0.0069 (7)
C2	0.0436 (7)	0.0406 (7)	0.0456 (8)	−0.0052 (6)	0.0258 (6)	−0.0029 (6)
C3	0.0428 (7)	0.0473 (8)	0.0339 (7)	−0.0055 (6)	0.0155 (6)	−0.0003 (6)
C4	0.0345 (6)	0.0408 (7)	0.0354 (7)	−0.0020 (5)	0.0153 (6)	0.0017 (5)
C5	0.0294 (6)	0.0405 (7)	0.0348 (7)	0.0003 (5)	0.0155 (5)	0.0020 (5)
C6	0.0354 (7)	0.0472 (8)	0.0378 (7)	0.0017 (6)	0.0120 (6)	0.0091 (6)
C7	0.0413 (7)	0.0381 (7)	0.0512 (8)	0.0016 (6)	0.0226 (7)	0.0088 (6)
C8	0.0334 (6)	0.0463 (8)	0.0329 (7)	−0.0039 (6)	0.0133 (5)	0.0013 (6)
C9	0.0367 (7)	0.0406 (7)	0.0400 (7)	−0.0073 (6)	0.0194 (6)	−0.0045 (6)
C10	0.0502 (8)	0.0401 (8)	0.0460 (8)	−0.0035 (6)	0.0150 (7)	0.0094 (6)
C11	0.0486 (8)	0.0484 (8)	0.0344 (7)	−0.0061 (7)	0.0062 (6)	0.0068 (6)
C12	0.0347 (6)	0.0360 (7)	0.0320 (6)	−0.0002 (5)	0.0129 (5)	0.0054 (5)
C13	0.0392 (7)	0.0280 (6)	0.0387 (7)	0.0009 (5)	0.0182 (6)	0.0028 (5)
C14	0.0540 (9)	0.0398 (8)	0.0697 (11)	0.0108 (7)	0.0262 (8)	0.0125 (7)
C15	0.0438 (7)	0.0304 (6)	0.0418 (7)	−0.0015 (5)	0.0259 (6)	−0.0060 (5)
C16	0.0458 (7)	0.0309 (6)	0.0289 (6)	−0.0017 (5)	0.0179 (6)	−0.0042 (5)
C17	0.0394 (7)	0.0328 (6)	0.0356 (7)	−0.0032 (5)	0.0146 (6)	−0.0097 (5)
C18	0.0382 (7)	0.0320 (6)	0.0394 (7)	−0.0071 (5)	0.0212 (6)	−0.0095 (5)
C19	0.0484 (8)	0.0291 (6)	0.0396 (7)	−0.0067 (5)	0.0229 (6)	0.0000 (5)
C20	0.0409 (7)	0.0285 (6)	0.0294 (6)	0.0013 (5)	0.0121 (5)	0.0024 (5)
C21	0.0368 (7)	0.0350 (7)	0.0398 (7)	−0.0035 (5)	0.0192 (6)	−0.0096 (5)
C22	0.0745 (11)	0.0542 (9)	0.0339 (7)	−0.0095 (8)	0.0272 (7)	−0.0063 (7)
C23	0.0519 (9)	0.0570 (9)	0.0674 (10)	−0.0215 (7)	0.0370 (8)	−0.0208 (8)

Geometric parameters (Å, º) top

O1—C1	1.2031 (19)	C12—C13	1.5267 (18)
O2—C12	1.3569 (15)	C13—C15	1.5358 (18)
O2—C9	1.4071 (16)	C13—C19	1.5363 (18)
O3—C12	1.1971 (16)	C13—C14	1.5477 (19)
O4—C20	1.2136 (15)	C14—H14A	0.9600
O5—C21	1.2132 (15)	C14—H14B	0.9600
N1—C21	1.3828 (17)	C14—H14C	0.9600
N1—C20	1.3822 (17)	C15—C16	1.5473 (18)
N1—H22	0.8701	C15—H15A	0.9700
C1—C2	1.475 (2)	C15—H15B	0.9700
C1—H1	0.9300	C16—C20	1.5218 (17)
C2—C3	1.3707 (19)	C16—C17	1.5264 (19)
C2—C7	1.411 (2)	C16—C22	1.5284 (18)
C3—C4	1.4115 (19)	C17—C18	1.5266 (18)
C3—H3	0.9300	C17—H17A	0.9700
C4—C11	1.4138 (19)	C17—H17B	0.9700
C4—C5	1.4199 (18)	C18—C21	1.5177 (17)
C5—C8	1.4118 (18)	C18—C23	1.5289 (19)
C5—C6	1.4169 (18)	C18—C19	1.5388 (19)
C6—C7	1.356 (2)	C19—H19A	0.9700
C6—H6	0.9300	C19—H19B	0.9700
C7—H7	0.9300	C22—H22A	0.9600
C8—C9	1.3542 (19)	C22—H22B	0.9600
C8—H8	0.9300	C22—H22C	0.9600
C9—C10	1.400 (2)	C23—H23A	0.9600
C10—C11	1.363 (2)	C23—H23B	0.9600
C10—H10	0.9300	C23—H23C	0.9600
C11—H11	0.9300

C12—O2—C9	119.29 (10)	H14A—C14—H14C	109.5
C21—N1—C20	127.75 (10)	H14B—C14—H14C	109.5
C21—N1—H22	115.3	C13—C15—C16	116.17 (10)
C20—N1—H22	116.7	C13—C15—H15A	108.2
O1—C1—C2	124.44 (16)	C16—C15—H15A	108.2
O1—C1—H1	117.8	C13—C15—H15B	108.2
C2—C1—H1	117.8	C16—C15—H15B	108.2
C3—C2—C7	119.69 (13)	H15A—C15—H15B	107.4
C3—C2—C1	119.70 (13)	C20—C16—C17	108.48 (10)
C7—C2—C1	120.56 (13)	C20—C16—C22	109.31 (11)
C2—C3—C4	121.31 (13)	C17—C16—C22	111.87 (11)
C2—C3—H3	119.3	C20—C16—C15	109.00 (10)
C4—C3—H3	119.3	C17—C16—C15	109.17 (10)
C3—C4—C11	123.08 (12)	C22—C16—C15	108.96 (11)
C3—C4—C5	118.67 (12)	C16—C17—C18	110.81 (10)
C11—C4—C5	118.26 (12)	C16—C17—H17A	109.5
C8—C5—C6	122.23 (12)	C18—C17—H17A	109.5
C8—C5—C4	119.16 (12)	C16—C17—H17B	109.5
C6—C5—C4	118.61 (12)	C18—C17—H17B	109.5
C7—C6—C5	121.33 (12)	H17A—C17—H17B	108.1
C7—C6—H6	119.3	C21—C18—C17	109.17 (10)
C5—C6—H6	119.3	C21—C18—C23	108.94 (11)
C6—C7—C2	120.38 (12)	C17—C18—C23	111.52 (11)
C6—C7—H7	119.8	C21—C18—C19	108.07 (10)
C2—C7—H7	119.8	C17—C18—C19	109.68 (10)
C9—C8—C5	119.91 (12)	C23—C18—C19	109.38 (12)
C9—C8—H8	120.0	C13—C19—C18	115.92 (10)
C5—C8—H8	120.0	C13—C19—H19A	108.3
C8—C9—C10	122.17 (12)	C18—C19—H19A	108.3
C8—C9—O2	116.93 (12)	C13—C19—H19B	108.3
C10—C9—O2	120.76 (12)	C18—C19—H19B	108.3
C11—C10—C9	118.73 (13)	H19A—C19—H19B	107.4
C11—C10—H10	120.6	O4—C20—N1	119.48 (11)
C9—C10—H10	120.6	O4—C20—C16	123.81 (12)
C10—C11—C4	121.71 (13)	N1—C20—C16	116.71 (10)
C10—C11—H11	119.1	O5—C21—N1	120.38 (11)
C4—C11—H11	119.1	O5—C21—C18	122.93 (12)
O3—C12—O2	123.39 (12)	N1—C21—C18	116.66 (11)
O3—C12—C13	125.33 (12)	C16—C22—H22A	109.5
O2—C12—C13	111.13 (11)	C16—C22—H22B	109.5
C12—C13—C15	113.79 (10)	H22A—C22—H22B	109.5
C12—C13—C19	110.93 (10)	C16—C22—H22C	109.5
C15—C13—C19	109.93 (11)	H22A—C22—H22C	109.5
C12—C13—C14	103.54 (11)	H22B—C22—H22C	109.5
C15—C13—C14	109.47 (11)	C18—C23—H23A	109.5
C19—C13—C14	108.91 (11)	C18—C23—H23B	109.5
C13—C14—H14A	109.5	H23A—C23—H23B	109.5
C13—C14—H14B	109.5	C18—C23—H23C	109.5
H14A—C14—H14B	109.5	H23A—C23—H23C	109.5
C13—C14—H14C	109.5	H23B—C23—H23C	109.5

O1—C1—C2—C3	175.94 (17)	C12—C13—C15—C16	−79.40 (14)
O1—C1—C2—C7	−1.4 (3)	C19—C13—C15—C16	45.71 (14)
C7—C2—C3—C4	−0.3 (2)	C14—C13—C15—C16	165.31 (11)
C1—C2—C3—C4	−177.65 (13)	C13—C15—C16—C20	64.94 (14)
C2—C3—C4—C11	179.38 (14)	C13—C15—C16—C17	−53.40 (14)
C2—C3—C4—C5	−0.3 (2)	C13—C15—C16—C22	−175.85 (11)
C3—C4—C5—C8	−178.46 (12)	C20—C16—C17—C18	−59.52 (13)
C11—C4—C5—C8	1.79 (19)	C22—C16—C17—C18	179.83 (11)
C3—C4—C5—C6	1.19 (19)	C15—C16—C17—C18	59.14 (13)
C11—C4—C5—C6	−178.56 (13)	C16—C17—C18—C21	58.72 (13)
C8—C5—C6—C7	178.15 (13)	C16—C17—C18—C23	179.15 (11)
C4—C5—C6—C7	−1.5 (2)	C16—C17—C18—C19	−59.53 (13)
C5—C6—C7—C2	0.9 (2)	C12—C13—C19—C18	81.06 (13)
C3—C2—C7—C6	0.0 (2)	C15—C13—C19—C18	−45.66 (14)
C1—C2—C7—C6	177.36 (13)	C14—C13—C19—C18	−165.61 (12)
C6—C5—C8—C9	179.57 (13)	C21—C18—C19—C13	−65.35 (14)
C4—C5—C8—C9	−0.79 (19)	C17—C18—C19—C13	53.57 (14)
C5—C8—C9—C10	−1.3 (2)	C23—C18—C19—C13	176.18 (11)
C5—C8—C9—O2	−177.05 (11)	C21—N1—C20—O4	178.38 (13)
C12—O2—C9—C8	−121.10 (13)	C21—N1—C20—C16	−2.65 (19)
C12—O2—C9—C10	63.13 (17)	C17—C16—C20—O4	−150.00 (13)
C8—C9—C10—C11	2.4 (2)	C22—C16—C20—O4	−27.77 (19)
O2—C9—C10—C11	177.95 (13)	C15—C16—C20—O4	91.23 (15)
C9—C10—C11—C4	−1.3 (2)	C17—C16—C20—N1	31.08 (15)
C3—C4—C11—C10	179.53 (15)	C22—C16—C20—N1	153.30 (12)
C5—C4—C11—C10	−0.7 (2)	C15—C16—C20—N1	−87.70 (14)
C9—O2—C12—O3	−3.89 (19)	C20—N1—C21—O5	179.58 (13)
C9—O2—C12—C13	−179.69 (11)	C20—N1—C21—C18	1.5 (2)
O3—C12—C13—C15	150.90 (13)	C17—C18—C21—O5	152.91 (13)
O2—C12—C13—C15	−33.39 (14)	C23—C18—C21—O5	30.91 (18)
O3—C12—C13—C19	26.33 (18)	C19—C18—C21—O5	−87.84 (15)
O2—C12—C13—C19	−157.96 (10)	C17—C18—C21—N1	−29.08 (16)
O3—C12—C13—C14	−90.35 (16)	C23—C18—C21—N1	−151.08 (13)
O2—C12—C13—C14	85.35 (13)	C19—C18—C21—N1	90.17 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H22···O5ⁱ	0.87	2.02	2.8776 (14)	166

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃NO₅
M_r	393.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.896 (2), 11.692 (2), 16.636 (2)
β (°)	121.124 (9)
V (Å³)	1980.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.974, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10443, 3897, 3217
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.03
No. of reflections	3897
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H22···O5ⁱ	0.87	2.02	2.8776 (14)	166

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by the Natural Science Foundation of Ludong University and the Students Research Fund of Ludong University.

References

Askew, B., Ballester, P., Buhr, C., Jeong, K. S., Jones, S., Parris, K., Williams, K. & Rebek, J. Jr (1989). J. Am. Chem. Soc. 111, 1082–1090. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chamontin, K., Lokshin, V., Rossollin, V., Samat, A. & Guglielmetti, R. (1999). Tetrahedron, 55, 5821–5830. Web of Science CrossRef CAS Google Scholar
Rebek, J. Jr, Askew, B., Killoran, M., Nemeth, D. & Lin, F. T. (1987). J. Am. Chem. Soc. 109, 2426–2431. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steglich, W. & Höfle, G. (1969). Angew. Chem. Int. Ed. Engl. 8, 981. CrossRef Web of Science Google Scholar
Williams, K., Askew, B., Ballester, P., Buhr, C., Jeong, K. S., Jones, S. & Rebek, J. Jr (1989). J. Am. Chem. Soc. 111, 1090–1094. CrossRef CAS Web of Science Google Scholar
Xu, S.-G. & Giuseppone, N. (2008). J. Am. Chem. Soc. 130, 1826–1827. Web of Science CrossRef PubMed CAS Google Scholar

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Volume 66| Part 1| January 2010| Page o245

doi:10.1107/S1600536809054786

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

6-Formyl-2-naphthyl cis-1,5,7-tri­methyl-2,4-dioxo-3-aza­bi­cyclo­[3.3.1]nonane-7-carboxyl­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-azabicyclo[3.3.1]nonane-7-carboxylate