N-Methacryloyl-4-(piperidin-1-yl)-1,8-naphthalimide.

In the title compound, C(21)H(20)N(2)O(3), the naphthalimide unit is almost planar (r.m.s. deviation for the 15 non-H atoms = 0.059 Å). The carboximide N atom and the five C atoms of the 2-methyl-prop-2-enoyl substituent also lie in a plane (r.m.s. deviation = 0.009 Å), which subtends an angle of 84.34 (7)° to the naphthalamide plane. This orients the =CH(2) group of the vinyl fragment towards the naphthalimide rings, giving the mol-ecule an extended configuration. The piperidine ring adopts a chair conformation and there is evidence for some delocalization between the naphthalene and piperidine units, the C-N(pip) bond length being 1.404 (4) Å. In the crystal structure, π-π contacts with centroid-centroid distances of 3.5351 (18) and 3.7794 (18) Å supported by C-H⋯O hydrogen bonds link adjacent mol-ecules in a head-to-tail fashion, forming dimers. These are further stabilized by other C-H⋯O contacts of varying strength, which stack the mol-ecules down the b axis.

Related literature

For background to the applications of 1,8-naphthalamides, see: McAdam et al. (2003 ▶, 2010 ▶); Flood et al. (2007 ▶). For their incorporation into polymer systems, see: Dana et al. (2007 ▶); Munro et al. (2008 ▶). For related structures, see: McAdam et al. (2003 ▶); Easton et al. (1992 ▶); Batchelor et al. (1997 ▶); Tagg et al. (2008 ▶). For comparative bond-length data, see: Allen et al. (1987 ▶) and for ring conformations, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C21H20N2O3

M = 348.39

Monoclinic,

a = 29.049 (3) Å

b = 6.9852 (7) Å

c = 17.1503 (17) Å

β = 102.013 (6)°

V = 3403.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 90 K

0.65 × 0.11 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.838, T max = 1.000

12211 measured reflections

1843 independent reflections

1440 reflections with I > 2σ(I)

R int = 0.075

θmax = 21.2°

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.152

S = 1.12

1843 reflections

236 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN2000 (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810018994/hb5457sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810018994/hb5457Isup2.hkl

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

C21H20N2O3	F(000) = 1472
Mr = 348.39	Dx = 1.360 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2032 reflections
a = 29.049 (3) Å	θ = 2.4–21.1°
b = 6.9852 (7) Å	µ = 0.09 mm−1
c = 17.1503 (17) Å	T = 90 K
β = 102.013 (6)°	Blade, orange
V = 3403.7 (6) Å3	0.65 × 0.11 × 0.04 mm
Z = 8

Bruker APEXII CCD diffractometer	1843 independent reflections
Radiation source: fine-focus sealed tube	1440 reflections with I > 2σ(I)
graphite	Rint = 0.075
ω scans	θmax = 21.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −29→29
Tmin = 0.838, Tmax = 1.000	k = −7→6
12211 measured reflections	l = −17→17

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0822P)2] where P = (Fo2 + 2Fc2)/3
1843 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 > 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
C1	0.70398 (11)	0.5991 (4)	0.6119 (2)	0.0221 (9)
C2	0.72082 (12)	0.6631 (5)	0.6879 (2)	0.0237 (9)
H2	0.6991	0.7017	0.7193	0.028*
C3	0.76855 (12)	0.6733 (5)	0.7204 (2)	0.0242 (9)
H3	0.7788	0.7212	0.7730	0.029*
C4	0.80161 (12)	0.6150 (4)	0.6777 (2)	0.0217 (9)
C5	0.81694 (12)	0.5175 (4)	0.5443 (2)	0.0227 (9)
H5	0.8499	0.5270	0.5640	0.027*
C6	0.80025 (12)	0.4695 (4)	0.4661 (2)	0.0255 (9)
H6	0.8219	0.4450	0.4326	0.031*
C7	0.75190 (12)	0.4560 (4)	0.4347 (2)	0.0225 (9)
H7	0.7408	0.4207	0.3805	0.027*
C8	0.72057 (12)	0.4939 (4)	0.4825 (2)	0.0217 (9)
C9	0.73615 (12)	0.5448 (4)	0.5643 (2)	0.0201 (9)
C10	0.78588 (12)	0.5534 (4)	0.5964 (2)	0.0218 (9)
C11	0.66975 (13)	0.4926 (4)	0.4468 (2)	0.0236 (9)
C12	0.65327 (13)	0.5993 (5)	0.5773 (2)	0.0236 (9)
C13	0.58901 (13)	0.5604 (5)	0.4598 (2)	0.0303 (10)
C14	0.56012 (12)	0.3865 (5)	0.4482 (2)	0.0294 (10)
C15	0.57626 (13)	0.2257 (5)	0.4834 (2)	0.0351 (10)
H15A	0.6068	0.2217	0.5166	0.042*
H15B	0.5574	0.1135	0.4757	0.042*
C16	0.51218 (13)	0.4093 (6)	0.3979 (3)	0.0469 (12)
H16A	0.4953	0.2871	0.3951	0.070*
H16B	0.5147	0.4489	0.3441	0.070*
H16C	0.4949	0.5068	0.4213	0.070*
C21	0.87594 (12)	0.4410 (5)	0.7217 (2)	0.0300 (10)
H21A	0.8647	0.3562	0.6754	0.036*
H21B	0.8694	0.3770	0.7697	0.036*
C22	0.92823 (12)	0.4714 (5)	0.7318 (2)	0.0346 (10)
H22A	0.9352	0.5248	0.6821	0.041*
H22B	0.9447	0.3471	0.7424	0.041*
C23	0.94596 (13)	0.6084 (5)	0.8008 (2)	0.0380 (11)
H23A	0.9424	0.5491	0.8516	0.046*
H23B	0.9798	0.6360	0.8043	0.046*
C24	0.91787 (12)	0.7929 (5)	0.7872 (2)	0.0350 (10)
H24A	0.9281	0.8790	0.8334	0.042*
H24B	0.9242	0.8580	0.7392	0.042*
C25	0.86568 (12)	0.7558 (5)	0.7762 (2)	0.0300 (9)
H25A	0.8588	0.6991	0.8254	0.036*
H25B	0.8483	0.8781	0.7658	0.036*
N1	0.63959 (9)	0.5398 (4)	0.49807 (17)	0.0237 (8)
N2	0.85019 (10)	0.6250 (4)	0.70929 (16)	0.0262 (8)
O1	0.57432 (8)	0.7182 (4)	0.43997 (15)	0.0387 (7)
O11	0.65310 (8)	0.4540 (3)	0.37740 (14)	0.0293 (7)
O12	0.62306 (9)	0.6481 (3)	0.61341 (15)	0.0331 (7)

	U11	U22	U33	U12	U13	U23
C1	0.020 (2)	0.018 (2)	0.026 (2)	−0.0025 (15)	−0.0009 (18)	−0.0004 (16)
C2	0.028 (2)	0.021 (2)	0.024 (2)	0.0006 (16)	0.0074 (19)	0.0028 (16)
C3	0.024 (2)	0.024 (2)	0.024 (2)	−0.0007 (16)	0.0020 (18)	0.0024 (16)
C4	0.021 (2)	0.0138 (19)	0.029 (2)	−0.0024 (15)	0.0029 (19)	0.0030 (15)
C5	0.021 (2)	0.0160 (19)	0.031 (2)	0.0053 (15)	0.0041 (18)	0.0035 (16)
C6	0.029 (2)	0.022 (2)	0.027 (2)	0.0027 (16)	0.0106 (19)	0.0023 (16)
C7	0.027 (2)	0.0163 (19)	0.022 (2)	0.0003 (15)	0.0016 (18)	−0.0002 (15)
C8	0.028 (2)	0.0070 (19)	0.029 (2)	0.0007 (15)	0.0031 (19)	0.0015 (15)
C9	0.021 (2)	0.0130 (19)	0.026 (2)	−0.0017 (15)	0.0034 (18)	0.0024 (16)
C10	0.028 (2)	0.0116 (18)	0.024 (2)	−0.0012 (15)	0.0005 (18)	0.0025 (15)
C11	0.029 (2)	0.016 (2)	0.025 (2)	0.0004 (16)	0.003 (2)	0.0036 (16)
C12	0.026 (2)	0.020 (2)	0.025 (2)	−0.0007 (17)	0.008 (2)	0.0005 (17)
C13	0.029 (2)	0.028 (3)	0.031 (2)	0.0066 (19)	0.0008 (19)	0.0009 (18)
C14	0.027 (2)	0.031 (3)	0.028 (2)	−0.0014 (19)	0.0020 (18)	−0.0012 (18)
C15	0.029 (2)	0.032 (3)	0.042 (3)	−0.0043 (19)	0.002 (2)	−0.003 (2)
C16	0.030 (2)	0.050 (3)	0.053 (3)	0.002 (2)	−0.011 (2)	−0.001 (2)
C21	0.027 (2)	0.024 (2)	0.036 (2)	0.0026 (16)	−0.0004 (19)	0.0035 (17)
C22	0.030 (2)	0.037 (2)	0.035 (2)	0.0060 (18)	0.0037 (19)	0.0006 (18)
C23	0.024 (2)	0.050 (3)	0.038 (3)	0.0006 (19)	0.0013 (19)	−0.008 (2)
C24	0.028 (2)	0.042 (3)	0.033 (2)	−0.0062 (18)	0.0034 (19)	−0.0139 (18)
C25	0.026 (2)	0.034 (2)	0.028 (2)	−0.0011 (17)	0.0019 (18)	−0.0093 (18)
N1	0.0192 (18)	0.0226 (17)	0.0269 (19)	−0.0013 (13)	−0.0011 (15)	−0.0011 (13)
N2	0.0242 (19)	0.0272 (18)	0.0248 (18)	0.0010 (14)	−0.0007 (14)	−0.0044 (14)
O1	0.0375 (17)	0.0292 (17)	0.0462 (18)	0.0089 (13)	0.0015 (14)	0.0043 (13)
O11	0.0325 (17)	0.0280 (15)	0.0238 (16)	−0.0017 (11)	−0.0024 (13)	−0.0014 (11)
O12	0.0269 (16)	0.0365 (16)	0.0349 (17)	−0.0011 (12)	0.0043 (14)	−0.0032 (12)

C1—C2	1.368 (5)	C13—N1	1.486 (4)
C1—C9	1.415 (5)	C14—C15	1.315 (5)
C1—C12	1.469 (5)	C14—C16	1.486 (5)
C2—C3	1.384 (5)	C15—H15A	0.9500
C2—H2	0.9500	C15—H15B	0.9500
C3—C4	1.385 (5)	C16—H16A	0.9800
C3—H3	0.9500	C16—H16B	0.9800
C4—N2	1.404 (4)	C16—H16C	0.9800
C4—C10	1.440 (5)	C21—N2	1.480 (4)
C5—C6	1.370 (4)	C21—C22	1.508 (5)
C5—C10	1.418 (5)	C21—H21A	0.9900
C5—H5	0.9500	C21—H21B	0.9900
C6—C7	1.399 (5)	C22—C23	1.525 (5)
C6—H6	0.9500	C22—H22A	0.9900
C7—C8	1.372 (5)	C22—H22B	0.9900
C7—H7	0.9500	C23—C24	1.517 (5)
C8—C9	1.426 (5)	C23—H23A	0.9900
C8—C11	1.476 (5)	C23—H23B	0.9900
C9—C10	1.436 (5)	C24—C25	1.511 (5)
C11—O11	1.218 (4)	C24—H24A	0.9900
C11—N1	1.403 (4)	C24—H24B	0.9900
C12—O12	1.223 (4)	C25—N2	1.462 (4)
C12—N1	1.397 (4)	C25—H25A	0.9900
C13—O1	1.205 (4)	C25—H25B	0.9900
C13—C14	1.466 (5)
C2—C1—C9	119.3 (3)	H15A—C15—H15B	120.0
C2—C1—C12	121.0 (3)	C14—C16—H16A	109.5
C9—C1—C12	119.6 (3)	C14—C16—H16B	109.5
C1—C2—C3	122.0 (3)	H16A—C16—H16B	109.5
C1—C2—H2	119.0	C14—C16—H16C	109.5
C3—C2—H2	119.0	H16A—C16—H16C	109.5
C2—C3—C4	121.2 (3)	H16B—C16—H16C	109.5
C2—C3—H3	119.4	N2—C21—C22	111.2 (3)
C4—C3—H3	119.4	N2—C21—H21A	109.4
C3—C4—N2	122.2 (3)	C22—C21—H21A	109.4
C3—C4—C10	119.0 (3)	N2—C21—H21B	109.4
N2—C4—C10	118.7 (3)	C22—C21—H21B	109.4
C6—C5—C10	121.2 (3)	H21A—C21—H21B	108.0
C6—C5—H5	119.4	C21—C22—C23	110.3 (3)
C10—C5—H5	119.4	C21—C22—H22A	109.6
C5—C6—C7	121.0 (3)	C23—C22—H22A	109.6
C5—C6—H6	119.5	C21—C22—H22B	109.6
C7—C6—H6	119.5	C23—C22—H22B	109.6
C8—C7—C6	119.7 (3)	H22A—C22—H22B	108.1
C8—C7—H7	120.2	C24—C23—C22	109.3 (3)
C6—C7—H7	120.2	C24—C23—H23A	109.8
C7—C8—C9	121.4 (3)	C22—C23—H23A	109.8
C7—C8—C11	118.8 (3)	C24—C23—H23B	109.8
C9—C8—C11	119.6 (3)	C22—C23—H23B	109.8
C1—C9—C8	121.5 (3)	H23A—C23—H23B	108.3
C1—C9—C10	120.0 (3)	C25—C24—C23	111.5 (3)
C8—C9—C10	118.4 (3)	C25—C24—H24A	109.3
C5—C10—C9	118.2 (3)	C23—C24—H24A	109.3
C5—C10—C4	123.2 (3)	C25—C24—H24B	109.3
C9—C10—C4	118.4 (3)	C23—C24—H24B	109.3
O11—C11—N1	119.4 (3)	H24A—C24—H24B	108.0
O11—C11—C8	124.5 (3)	N2—C25—C24	110.0 (3)
N1—C11—C8	116.1 (3)	N2—C25—H25A	109.7
O12—C12—N1	119.1 (3)	C24—C25—H25A	109.7
O12—C12—C1	124.1 (3)	N2—C25—H25B	109.7
N1—C12—C1	116.8 (3)	C24—C25—H25B	109.7
O1—C13—C14	124.1 (3)	H25A—C25—H25B	108.2
O1—C13—N1	118.2 (3)	C12—N1—C11	126.2 (3)
C14—C13—N1	117.7 (3)	C12—N1—C13	117.1 (3)
C15—C14—C13	120.4 (3)	C11—N1—C13	115.8 (3)
C15—C14—C16	124.0 (3)	C4—N2—C25	117.0 (3)
C13—C14—C16	115.5 (3)	C4—N2—C21	116.7 (2)
C14—C15—H15A	120.0	C25—N2—C21	111.5 (3)
C14—C15—H15B	120.0

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O12i	0.99	2.54	3.485 (4)	160
C24—H24A···O12ii	0.99	2.67	3.365 (4)	127
C21—H21A···O11iii	0.99	2.36	3.258 (4)	150
C25—H25B···O11iv	0.99	2.72	3.278 (4)	117

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯O12i	0.99	2.54	3.485 (4)	160
C24—H24A⋯O12ii	0.99	2.67	3.365 (4)	127
C21—H21A⋯O11iii	0.99	2.36	3.258 (4)	150
C25—H25B⋯O11iv	0.99	2.72	3.278 (4)	117

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .