6-Formyl-2-naphthyl cis-1,5,7-trimethyl-2,4-dioxo-3-aza-bicyclo-[3.3.1]nonane-7-carboxyl-ate.

In the title compound, C(23)H(23)NO(5), the C(5)N ring adopts an envelope conformation with a C atom as the flap, whilst the saturated C(6) ring fused to it adopts a chair conformation. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R(2) (2)(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 = 393.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.03

3897 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

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.

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

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

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

C23H23NO5	F(000) = 832
Mr = 393.42	Dx = 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

Bruker APEXII CCD diffractometer	3897 independent reflections
Radiation source: fine-focus sealed tube	3217 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scan	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→14
Tmin = 0.974, Tmax = 0.982	k = −14→14
10443 measured reflections	l = −20→20

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(Fo2) + (0.0518P)2 + 0.4083P] where P = (Fo2 + 2Fc2)/3
3897 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .