(1R*,2S*,3R*,4S*)-N-(1-Naphth­yl)-5-norbornene-2,3-dicarboximide

In the title compound, C₁₉H₁₅NO₂, the norbornene is fused to a cyclo­dicarbonimide, and the naphthyl ring is directly linked to the N atom. The crystal packing is stabilized by two kinds of inter­molecular C—H...O hydrogen bonds and one intra­molecular C—H...N hydrogen bond as well as by C—H...π-ring inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.102
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.50
           From the CIF: _reflns_number_total               1934
           Count of symmetry unique reflns         1954
           Completeness (_total/calc)             98.98%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT0Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

(1R*,2S*,3R*,4S*)-N-(1-Naphthyl)-5-norbornene-2,3-dicarboximide

Crystal data

C19H15NO2	Dx = 1.312 Mg m^−3
Mr = 289.32	Melting point: 503 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2201 reflections
a = 7.2279 (7) Å	θ = 2.2–23.1°
b = 10.2493 (10) Å	µ = 0.09 mm^−1
c = 19.7706 (19) Å	T = 298 K
V = 1464.6 (2) Å^3	Block, colourless
Z = 4	0.30 × 0.16 × 0.10 mm
F(000) = 608

Data collection

Bruker SMART 4K CCD area-detector diffractometer	1638 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
Graphite monochromator	θmax = 27.5°, θmin = 2.1°
φ and ω scans	h = −9→9
8887 measured reflections	k = −13→10
1934 independent reflections	l = −25→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: difference Fourier map
wR(F^2) = 0.102	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.2137P] where P = (Fo^2 + 2Fc^2)/3
1934 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3
60 constraints

Special details

Experimental. Spectroscopic analysis: IR (KBr, ν cm^-1): 3048, 2986, 2941, 1710, 1590, 1402, 1372; ¹H NMR (CDCl3, δ, p.p.m.): 7.90–7.00 (m, 7H), 6.60–6.28 (d, 2H), 3.42–3.68 (s, 4H), 1.50–2.00 (m, 2H). analysis, calculated for C₁₉H₁₅NO₂: C 78.89, H 5.19, N 4.84%; found: C 78.91, H 5.15, N 4.88%.

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5374 (4)	0.3363 (3)	−0.08123 (15)	0.0602 (8)
H1	0.4838	0.2611	−0.0637	0.072*
C2	0.4498 (4)	0.4320 (3)	−0.11155 (13)	0.0566 (8)
H2	0.3230	0.4369	−0.1190	0.068*
C3	0.7403 (4)	0.3701 (3)	−0.07993 (13)	0.0541 (7)
H3	0.8260	0.2970	−0.0736	0.065*
C4	0.5904 (4)	0.5325 (3)	−0.13217 (11)	0.0497 (7)
H4	0.5533	0.5919	−0.1686	0.060*
C5	0.7566 (4)	0.4447 (3)	−0.14702 (12)	0.0569 (7)
H5A	0.8717	0.4928	−0.1511	0.068*
H5B	0.7383	0.3894	−0.1863	0.068*
C6	0.7611 (3)	0.4868 (2)	−0.02952 (11)	0.0425 (6)
H6	0.8917	0.5084	−0.0222	0.051*
C7	0.6603 (4)	0.5979 (2)	−0.06582 (11)	0.0398 (5)
H7	0.7456	0.6697	−0.0760	0.048*
C8	0.6608 (3)	0.4701 (2)	0.03672 (11)	0.0410 (5)
C9	0.5127 (4)	0.6415 (2)	−0.01804 (11)	0.0411 (6)
C10	0.3941 (3)	0.5754 (2)	0.09529 (10)	0.0376 (5)
C11	0.2305 (4)	0.5106 (3)	0.09166 (13)	0.0492 (6)
H11	0.2048	0.4586	0.0543	0.059*
C12	0.1002 (4)	0.5214 (3)	0.14377 (14)	0.0584 (7)
H12	−0.0113	0.4764	0.1411	0.070*
C13	0.1368 (4)	0.5977 (3)	0.19817 (13)	0.0530 (7)
H13	0.0490	0.6050	0.2324	0.064*
C14	0.3052 (4)	0.6662 (2)	0.20401 (11)	0.0413 (6)
C15	0.3445 (4)	0.7491 (3)	0.25974 (12)	0.0512 (7)
H15	0.2575	0.7579	0.2941	0.061*
C16	0.5054 (5)	0.8152 (3)	0.26383 (13)	0.0566 (7)
H16	0.5282	0.8691	0.3007	0.068*
C17	0.6388 (5)	0.8030 (3)	0.21247 (12)	0.0570 (7)
H17	0.7499	0.8483	0.2158	0.068*
C18	0.6065 (4)	0.7248 (2)	0.15747 (12)	0.0458 (6)
H18	0.6957	0.7177	0.1238	0.055*
C19	0.4392 (3)	0.6551 (2)	0.15164 (11)	0.0373 (5)
N1	0.5238 (3)	0.56480 (18)	0.04034 (9)	0.0387 (5)
O1	0.6884 (3)	0.39001 (19)	0.08002 (9)	0.0668 (6)
O2	0.3986 (3)	0.72625 (18)	−0.02588 (9)	0.0638 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.075 (2)	0.0452 (15)	0.0603 (17)	−0.0172 (15)	0.0089 (16)	−0.0196 (14)
C2	0.0508 (17)	0.0682 (19)	0.0509 (15)	−0.0097 (15)	−0.0069 (13)	−0.0223 (15)
C3	0.0659 (19)	0.0445 (14)	0.0519 (15)	0.0108 (14)	0.0080 (14)	−0.0081 (12)
C4	0.0618 (17)	0.0566 (15)	0.0308 (11)	0.0040 (14)	−0.0026 (12)	−0.0063 (11)
C5	0.0652 (18)	0.0649 (18)	0.0407 (13)	0.0015 (16)	0.0064 (13)	−0.0148 (13)
C6	0.0399 (12)	0.0481 (13)	0.0395 (12)	−0.0007 (11)	−0.0021 (10)	−0.0039 (11)
C7	0.0490 (14)	0.0364 (12)	0.0341 (11)	−0.0057 (11)	0.0013 (10)	−0.0011 (9)
C8	0.0400 (13)	0.0468 (13)	0.0364 (12)	0.0045 (11)	−0.0078 (10)	−0.0018 (10)
C9	0.0591 (16)	0.0340 (12)	0.0302 (11)	0.0019 (12)	−0.0039 (11)	−0.0033 (9)
C10	0.0453 (13)	0.0359 (11)	0.0316 (11)	0.0052 (11)	−0.0019 (10)	0.0044 (9)
C11	0.0557 (16)	0.0482 (14)	0.0436 (14)	−0.0004 (13)	−0.0102 (12)	−0.0013 (11)
C12	0.0446 (15)	0.0675 (18)	0.0630 (17)	−0.0095 (15)	−0.0013 (14)	0.0088 (15)
C13	0.0479 (16)	0.0643 (17)	0.0469 (14)	0.0039 (14)	0.0105 (12)	0.0113 (13)
C14	0.0485 (15)	0.0427 (13)	0.0328 (11)	0.0060 (12)	0.0031 (11)	0.0078 (10)
C15	0.0670 (18)	0.0545 (16)	0.0322 (12)	0.0106 (15)	0.0109 (12)	0.0022 (11)
C16	0.082 (2)	0.0534 (16)	0.0348 (13)	−0.0036 (16)	0.0003 (15)	−0.0066 (12)
C17	0.0671 (19)	0.0574 (17)	0.0465 (14)	−0.0134 (15)	−0.0043 (14)	−0.0041 (12)
C18	0.0535 (15)	0.0488 (13)	0.0350 (12)	−0.0042 (13)	0.0023 (11)	−0.0006 (11)
C19	0.0467 (14)	0.0366 (12)	0.0285 (11)	0.0066 (11)	0.0012 (10)	0.0064 (9)
N1	0.0490 (11)	0.0389 (10)	0.0282 (9)	0.0064 (9)	−0.0013 (8)	−0.0006 (8)
O1	0.0757 (14)	0.0749 (13)	0.0497 (11)	0.0334 (12)	0.0034 (10)	0.0224 (10)
O2	0.0918 (15)	0.0556 (11)	0.0441 (10)	0.0325 (12)	0.0060 (11)	0.0074 (9)

Geometric parameters (Å, º)

C1—C2	1.312 (4)	C9—N1	1.399 (3)
C1—C3	1.507 (4)	C10—C11	1.358 (4)
C1—H1	0.9300	C10—C19	1.420 (3)
C2—C4	1.503 (4)	C10—N1	1.439 (3)
C2—H2	0.9300	C11—C12	1.400 (4)
C3—C5	1.535 (4)	C11—H11	0.9300
C3—C6	1.564 (3)	C12—C13	1.356 (4)
C3—H3	0.9800	C12—H12	0.9300
C4—C5	1.530 (4)	C13—C14	1.410 (4)
C4—C7	1.557 (3)	C13—H13	0.9300
C4—H4	0.9800	C14—C15	1.420 (3)
C5—H5A	0.9700	C14—C19	1.422 (3)
C5—H5B	0.9700	C15—C16	1.349 (4)
C6—C8	1.507 (3)	C15—H15	0.9300
C6—C7	1.531 (3)	C16—C17	1.406 (4)
C6—H6	0.9800	C16—H16	0.9300
C7—C9	1.493 (3)	C17—C18	1.371 (3)
C7—H7	0.9800	C17—H17	0.9300
C8—O1	1.203 (3)	C18—C19	1.409 (3)
C8—N1	1.388 (3)	C18—H18	0.9300
C9—O2	1.208 (3)
C2—C1—C3	107.8 (3)	N1—C8—C6	108.00 (19)
C2—C1—H1	126.1	O2—C9—N1	123.3 (2)
C3—C1—H1	126.1	O2—C9—C7	128.4 (2)
C1—C2—C4	108.0 (3)	N1—C9—C7	108.23 (19)
C1—C2—H2	126.0	C11—C10—C19	121.5 (2)
C4—C2—H2	126.0	C11—C10—N1	119.4 (2)
C1—C3—C5	100.0 (3)	C19—C10—N1	119.1 (2)
C1—C3—C6	106.3 (2)	C10—C11—C12	120.5 (2)
C5—C3—C6	99.35 (19)	C10—C11—H11	119.7
C1—C3—H3	116.2	C12—C11—H11	119.7
C5—C3—H3	116.2	C13—C12—C11	119.9 (3)
C6—C3—H3	116.2	C13—C12—H12	120.1
C2—C4—C5	100.4 (2)	C11—C12—H12	120.1
C2—C4—C7	106.60 (19)	C12—C13—C14	121.4 (2)
C5—C4—C7	99.2 (2)	C12—C13—H13	119.3
C2—C4—H4	116.1	C14—C13—H13	119.3
C5—C4—H4	116.1	C13—C14—C15	122.3 (2)
C7—C4—H4	116.1	C13—C14—C19	119.2 (2)
C4—C5—C3	93.8 (2)	C15—C14—C19	118.5 (2)
C4—C5—H5A	113.0	C16—C15—C14	121.3 (2)
C3—C5—H5A	113.0	C16—C15—H15	119.4
C4—C5—H5B	113.0	C14—C15—H15	119.4
C3—C5—H5B	113.0	C15—C16—C17	120.2 (2)
H5A—C5—H5B	110.4	C15—C16—H16	119.9
C8—C6—C7	105.2 (2)	C17—C16—H16	119.9
C8—C6—C3	114.9 (2)	C18—C17—C16	120.6 (3)
C7—C6—C3	102.97 (18)	C18—C17—H17	119.7
C8—C6—H6	111.1	C16—C17—H17	119.7
C7—C6—H6	111.1	C17—C18—C19	120.5 (2)
C3—C6—H6	111.1	C17—C18—H18	119.8
C9—C7—C6	105.43 (18)	C19—C18—H18	119.8
C9—C7—C4	115.5 (2)	C18—C19—C10	123.6 (2)
C6—C7—C4	103.23 (19)	C18—C19—C14	119.0 (2)
C9—C7—H7	110.8	C10—C19—C14	117.4 (2)
C6—C7—H7	110.8	C8—N1—C9	113.04 (18)
C4—C7—H7	110.8	C8—N1—C10	123.79 (18)
O1—C8—N1	124.0 (2)	C9—N1—C10	122.90 (19)
O1—C8—C6	128.0 (2)
C3—C1—C2—C4	0.5 (3)	C10—C11—C12—C13	0.4 (4)
C2—C1—C3—C5	−33.4 (3)	C11—C12—C13—C14	−0.6 (4)
C2—C1—C3—C6	69.5 (3)	C12—C13—C14—C15	178.4 (3)
C1—C2—C4—C5	32.7 (3)	C12—C13—C14—C19	0.1 (4)
C1—C2—C4—C7	−70.2 (3)	C13—C14—C15—C16	−179.0 (2)
C2—C4—C5—C3	−49.4 (2)	C19—C14—C15—C16	−0.7 (4)
C7—C4—C5—C3	59.5 (2)	C14—C15—C16—C17	−0.1 (4)
C1—C3—C5—C4	49.5 (2)	C15—C16—C17—C18	0.6 (4)
C6—C3—C5—C4	−59.0 (2)	C16—C17—C18—C19	−0.2 (4)
C1—C3—C6—C8	46.7 (3)	C17—C18—C19—C10	178.2 (2)
C5—C3—C6—C8	150.1 (2)	C17—C18—C19—C14	−0.6 (3)
C1—C3—C6—C7	−67.2 (3)	C11—C10—C19—C18	−179.6 (2)
C5—C3—C6—C7	36.3 (3)	N1—C10—C19—C18	−0.6 (3)
C8—C6—C7—C9	1.7 (2)	C11—C10—C19—C14	−0.8 (3)
C3—C6—C7—C9	122.4 (2)	N1—C10—C19—C14	178.17 (19)
C8—C6—C7—C4	−119.8 (2)	C13—C14—C19—C18	179.4 (2)
C3—C6—C7—C4	0.9 (2)	C15—C14—C19—C18	1.0 (3)
C2—C4—C7—C9	−48.6 (3)	C13—C14—C19—C10	0.6 (3)
C5—C4—C7—C9	−152.4 (2)	C15—C14—C19—C10	−177.8 (2)
C2—C4—C7—C6	65.9 (3)	O1—C8—N1—C9	−176.5 (2)
C5—C4—C7—C6	−37.9 (2)	C6—C8—N1—C9	2.9 (3)
C7—C6—C8—O1	176.6 (2)	O1—C8—N1—C10	−2.3 (4)
C3—C6—C8—O1	64.1 (3)	C6—C8—N1—C10	177.1 (2)
C7—C6—C8—N1	−2.8 (2)	O2—C9—N1—C8	177.5 (2)
C3—C6—C8—N1	−115.3 (2)	C7—C9—N1—C8	−1.8 (3)
C6—C7—C9—O2	−179.3 (2)	O2—C9—N1—C10	3.2 (3)
C4—C7—C9—O2	−66.1 (3)	C7—C9—N1—C10	−176.1 (2)
C6—C7—C9—N1	−0.1 (2)	C11—C10—N1—C8	−90.3 (3)
C4—C7—C9—N1	113.2 (2)	C19—C10—N1—C8	90.7 (3)
C19—C10—C11—C12	0.3 (4)	C11—C10—N1—C9	83.3 (3)
N1—C10—C11—C12	−178.6 (2)	C19—C10—N1—C9	−95.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^i	0.98	2.53	3.082 (3)	115
C18—H18···O2^i	0.93	2.50	3.388 (3)	161
C18—H18···N1	0.93	2.59	2.900 (3)	100

Symmetry code: (i) x+1/2, −y+3/2, −z.