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In the title compound, C
19H
15NO
2, 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.
Supporting information
CCDC reference: 647195
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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.
(1
R*,2
S*,3
R*,4
S*)-
N-(1-Naphthyl)-5-norbornene-2,3-dicarboximide
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.16 × 0.10 mm |
F(000) = 608 | |
Data collection top
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 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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.102 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.041P)2 + 0.2137P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O2i | 0.98 | 2.53 | 3.082 (3) | 115 |
C18—H18···O2i | 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. |
D—H···π-ring interactions. Cg1 is a centroid of the
ring C10/C11/C12/C13/C14/C19 (Fig. 1). topD—H···Cg | D—H | H···Cg | D···Cg | D—H···Cg |
C7—H7···Cg1ii | 0.98 | 2.86 | 3.686 (2) | 142 |
C16—H16···Cg1iii | 0.93 | 2.87 | 3.683 (3) | 147 |
Symmetry codes: (ii) -x, 3/2+y, 1/2-z; (iii) 3/2+x, 1/2-y, -z. |
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