In the title compound, C
16H
15NO
3, the 1,8-naphthalenodicarboximide group is nearly planar and, in the naphthalimide ring system, the characteristic alternating pattern of bond lengths is observed. In the crystal, the molecules are connected by a weak C—H
O hydrogen bond and extend in the direction parallel to the
b axis.
Supporting information
CCDC reference: 206783
Key indicators
- Single-crystal X-ray study
- T = 90 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.100
- Data-to-parameter ratio = 14.0
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED; data reduction: CrysAlis RED (Oxford Diffraction, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Crystal data top
C16H15NO3 | Z = 2 |
Mr = 269.29 | F(000) = 284 |
Triclinic, P1 | Dx = 1.341 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.154 (1) Å | Cell parameters from 3178 reflections |
b = 9.554 (2) Å | θ = 4.2–28° |
c = 9.866 (2) Å | µ = 0.09 mm−1 |
α = 85.27 (3)° | T = 90 K |
β = 82.88 (3)° | Block, colourless |
γ = 89.57 (3)° | 0.6 × 0.5 × 0.5 mm |
V = 666.9 (2) Å3 | |
Data collection top
Xcalibur diffractometer | 1793 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 28°, θmin = 3.6° |
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1 | h = −8→9 |
ω scans | k = −13→12 |
5193 measured reflections | l = −12→13 |
3174 independent reflections | |
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) = 0.100 | All H-atom parameters refined |
S = 0.81 | w = 1/[σ2(Fo2) + (0.0483P)2] where P = (Fo2 + 2Fc2)/3 |
3174 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | Uiso*/Ueq | |
C1 | 0.25298 (19) | 0.02757 (14) | 0.01213 (15) | 0.0143 (3) | |
C2 | 0.2216 (2) | 0.07602 (16) | −0.11934 (15) | 0.0182 (3) | |
C3 | 0.1964 (2) | −0.02066 (17) | −0.21608 (16) | 0.0209 (4) | |
C4 | 0.2002 (2) | −0.16262 (17) | −0.17950 (16) | 0.0199 (3) | |
C5 | 0.2368 (2) | −0.36343 (16) | −0.00312 (17) | 0.0233 (4) | |
C6 | 0.2693 (2) | −0.41003 (17) | 0.12714 (18) | 0.0261 (4) | |
C7 | 0.2959 (2) | −0.31309 (16) | 0.22294 (18) | 0.0218 (4) | |
C8 | 0.2900 (2) | −0.16961 (15) | 0.18657 (15) | 0.0160 (3) | |
C9 | 0.25867 (19) | −0.11916 (15) | 0.05160 (15) | 0.0146 (3) | |
C10 | 0.2311 (2) | −0.21693 (16) | −0.04561 (16) | 0.0182 (3) | |
C11 | 0.3153 (2) | −0.06950 (15) | 0.28878 (15) | 0.0169 (3) | |
C12 | 0.2805 (2) | 0.12986 (15) | 0.11250 (15) | 0.0149 (3) | |
C13 | 0.3474 (2) | 0.17507 (16) | 0.34449 (16) | 0.0173 (3) | |
C14 | 0.1593 (2) | 0.21222 (18) | 0.42944 (16) | 0.0205 (3) | |
C15 | 0.1881 (3) | 0.30030 (16) | 0.54574 (17) | 0.0219 (4) | |
C16 | 0.2651 (3) | 0.52593 (19) | 0.59851 (18) | 0.0270 (4) | |
N1 | 0.31637 (16) | 0.07483 (12) | 0.24347 (12) | 0.0151 (3) | |
O1 | 0.33382 (16) | −0.10754 (11) | 0.40880 (11) | 0.0249 (3) | |
O2 | 0.27231 (15) | 0.25762 (10) | 0.08492 (11) | 0.0218 (3) | |
O3 | 0.24875 (16) | 0.43908 (11) | 0.49050 (11) | 0.0238 (3) | |
H2 | 0.219 (2) | 0.1770 (18) | −0.1424 (16) | 0.029* | |
H3 | 0.177 (2) | 0.0138 (17) | −0.3097 (17) | 0.029* | |
H4 | 0.183 (2) | −0.2281 (17) | −0.2463 (17) | 0.029* | |
H5 | 0.221 (2) | −0.4281 (17) | −0.0727 (17) | 0.029* | |
H6 | 0.272 (2) | −0.5115 (18) | 0.1567 (16) | 0.029* | |
H7 | 0.316 (2) | −0.3443 (17) | 0.3115 (18) | 0.029* | |
H13A | 0.410 (2) | 0.2593 (18) | 0.2948 (17) | 0.029* | |
H14A | 0.077 (2) | 0.2629 (17) | 0.3700 (16) | 0.029* | |
H15A | 0.067 (2) | 0.3068 (17) | 0.6098 (17) | 0.029* | |
H16A | 0.310 (2) | 0.622 (2) | 0.5567 (18) | 0.036* | |
H13B | 0.439 (2) | 0.1303 (17) | 0.4038 (17) | 0.029* | |
H14B | 0.088 (2) | 0.1209 (18) | 0.4688 (17) | 0.029* | |
H15B | 0.293 (2) | 0.2580 (17) | 0.6005 (17) | 0.029* | |
H16B | 0.137 (3) | 0.5277 (17) | 0.6644 (18) | 0.036* | |
H16C | 0.367 (3) | 0.4966 (18) | 0.6551 (18) | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0123 (7) | 0.0146 (7) | 0.0156 (7) | −0.0001 (6) | −0.0001 (6) | −0.0005 (6) |
C2 | 0.0165 (8) | 0.0191 (8) | 0.0183 (8) | 0.0009 (6) | 0.0002 (6) | −0.0004 (6) |
C3 | 0.0184 (8) | 0.0280 (9) | 0.0164 (8) | 0.0014 (7) | −0.0026 (6) | −0.0029 (7) |
C4 | 0.0151 (8) | 0.0243 (8) | 0.0211 (9) | 0.0008 (7) | −0.0007 (6) | −0.0101 (7) |
C5 | 0.0227 (9) | 0.0169 (8) | 0.0310 (10) | 0.0019 (7) | −0.0014 (7) | −0.0096 (7) |
C6 | 0.0307 (10) | 0.0122 (7) | 0.0344 (10) | −0.0011 (7) | −0.0007 (8) | −0.0018 (7) |
C7 | 0.0230 (9) | 0.0166 (8) | 0.0251 (9) | 0.0018 (7) | −0.0034 (7) | 0.0028 (7) |
C8 | 0.0146 (8) | 0.0136 (7) | 0.0192 (8) | −0.0005 (6) | 0.0001 (6) | −0.0010 (6) |
C9 | 0.0103 (7) | 0.0143 (7) | 0.0189 (8) | −0.0003 (6) | 0.0008 (6) | −0.0027 (6) |
C10 | 0.0135 (8) | 0.0188 (8) | 0.0224 (8) | −0.0016 (6) | 0.0010 (6) | −0.0056 (6) |
C11 | 0.0161 (8) | 0.0160 (7) | 0.0180 (8) | −0.0004 (6) | −0.0009 (6) | 0.0001 (6) |
C12 | 0.0136 (7) | 0.0156 (7) | 0.0150 (8) | 0.0001 (6) | 0.0004 (6) | −0.0007 (6) |
C13 | 0.0204 (8) | 0.0159 (7) | 0.0166 (8) | 0.0008 (6) | −0.0052 (6) | −0.0031 (6) |
C14 | 0.0209 (9) | 0.0214 (8) | 0.0191 (9) | −0.0006 (7) | −0.0011 (7) | −0.0033 (7) |
C15 | 0.0263 (9) | 0.0198 (8) | 0.0185 (8) | −0.0004 (7) | 0.0028 (7) | −0.0027 (7) |
C16 | 0.0356 (11) | 0.0222 (9) | 0.0239 (9) | −0.0005 (8) | −0.0028 (8) | −0.0066 (7) |
N1 | 0.0179 (7) | 0.0119 (6) | 0.0160 (7) | 0.0017 (5) | −0.0043 (5) | −0.0017 (5) |
O1 | 0.0343 (7) | 0.0218 (6) | 0.0189 (6) | 0.0018 (5) | −0.0078 (5) | 0.0020 (5) |
O2 | 0.0287 (6) | 0.0134 (5) | 0.0232 (6) | 0.0009 (5) | −0.0047 (5) | 0.0004 (4) |
O3 | 0.0366 (7) | 0.0175 (6) | 0.0172 (6) | −0.0002 (5) | −0.0012 (5) | −0.0034 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.385 (2) | C11—O1 | 1.2324 (17) |
C1—C9 | 1.425 (2) | C11—N1 | 1.413 (2) |
C1—C12 | 1.478 (2) | C12—O2 | 1.2310 (17) |
C2—C3 | 1.410 (2) | C12—N1 | 1.407 (2) |
C2—H2 | 0.973 (17) | C13—N1 | 1.4750 (18) |
C3—C4 | 1.375 (2) | C13—C14 | 1.550 (2) |
C3—H3 | 0.981 (17) | C13—H13A | 0.987 (17) |
C4—C10 | 1.422 (2) | C13—H13B | 1.002 (16) |
C4—H4 | 0.965 (16) | C14—C15 | 1.513 (2) |
C5—C6 | 1.372 (2) | C14—H14A | 0.978 (16) |
C5—C10 | 1.429 (2) | C14—H14B | 1.037 (17) |
C5—H5 | 0.978 (16) | C15—O3 | 1.4402 (19) |
C6—C7 | 1.407 (2) | C15—H15A | 1.014 (17) |
C6—H6 | 0.990 (17) | C15—H15B | 1.041 (17) |
C7—C8 | 1.390 (2) | C16—O3 | 1.4199 (19) |
C7—H7 | 0.928 (17) | C16—H16A | 1.008 (18) |
C8—C9 | 1.422 (2) | C16—H16B | 1.054 (18) |
C8—C11 | 1.474 (2) | C16—H16C | 0.996 (18) |
C9—C10 | 1.424 (2) | | |
| | | |
C2—C1—C9 | 120.87 (13) | N1—C11—C8 | 116.8 (1) |
C2—C1—C12 | 119.34 (13) | O2—C12—N1 | 120.6 (1) |
C9—C1—C12 | 119.79 (13) | O2—C12—C1 | 122.4 (1) |
C1—C2—C3 | 119.78 (14) | N1—C12—C1 | 116.9 (1) |
C1—C2—H2 | 118.5 (10) | N1—C13—C14 | 111.00 (12) |
C3—C2—H2 | 121.8 (10) | N1—C13—H13A | 108.2 (10) |
C4—C3—C2 | 120.13 (15) | C14—C13—H13A | 111.7 (10) |
C4—C3—H3 | 120.2 (9) | N1—C13—H13B | 106.9 (9) |
C2—C3—H3 | 119.7 (9) | C14—C13—H13B | 111.9 (9) |
C3—C4—C10 | 121.97 (14) | H13A—C13—H13B | 106.8 (13) |
C3—C4—H4 | 119.6 (10) | C15—C14—C13 | 112.47 (13) |
C10—C4—H4 | 118.4 (10) | C15—C14—H14A | 109.0 (9) |
C6—C5—C10 | 121.46 (15) | C13—C14—H14A | 109.9 (10) |
C6—C5—H5 | 122.1 (10) | C15—C14—H14B | 109.3 (9) |
C10—C5—H5 | 116.4 (10) | C13—C14—H14B | 109.9 (9) |
C5—C6—C7 | 120.13 (15) | H14A—C14—H14B | 106.1 (13) |
C5—C6—H6 | 121.3 (10) | O3—C15—C14 | 109.31 (13) |
C7—C6—H6 | 118.5 (10) | O3—C15—H15A | 109.5 (9) |
C8—C7—C6 | 120.43 (16) | C14—C15—H15A | 110.4 (9) |
C8—C7—H7 | 119.2 (10) | O3—C15—H15B | 107.1 (9) |
C6—C7—H7 | 120.3 (10) | C14—C15—H15B | 110.8 (9) |
C7—C8—C9 | 120.32 (14) | H15A—C15—H15B | 109.5 (13) |
C7—C8—C11 | 119.73 (14) | O3—C16—H16A | 108.2 (10) |
C9—C8—C11 | 119.95 (13) | O3—C16—H16B | 110.7 (9) |
C8—C9—C10 | 119.44 (13) | H16A—C16—H16B | 113.8 (14) |
C8—C9—C1 | 121.16 (13) | O3—C16—H16C | 113.8 (10) |
C10—C9—C1 | 119.39 (14) | H16A—C16—H16C | 102.3 (14) |
C4—C10—C9 | 117.85 (14) | H16B—C16—H16C | 107.9 (14) |
C4—C10—C5 | 123.92 (14) | C12—N1—C11 | 125.13 (12) |
C9—C10—C5 | 118.22 (14) | C12—N1—C13 | 117.81 (12) |
O1—C11—N1 | 120.5 (1) | C11—N1—C13 | 116.97 (12) |
O1—C11—C8 | 122.5 (1) | C16—O3—C15 | 110.10 (12) |
| | | |
C9—C1—C2—C3 | −0.5 (2) | C6—C5—C10—C9 | −0.5 (2) |
C12—C1—C2—C3 | 179.59 (14) | C7—C8—C11—O1 | −3.2 (2) |
C1—C2—C3—C4 | 0.9 (2) | C9—C8—C11—O1 | 176.42 (14) |
C2—C3—C4—C10 | −0.7 (2) | C7—C8—C11—N1 | 177.19 (13) |
C10—C5—C6—C7 | 0.7 (2) | C9—C8—C11—N1 | −3.1 (2) |
C5—C6—C7—C8 | −0.2 (2) | C2—C1—C12—O2 | 1.8 (2) |
C6—C7—C8—C9 | −0.6 (2) | C9—C1—C12—O2 | −178.13 (14) |
C6—C7—C8—C11 | 179.09 (14) | C2—C1—C12—N1 | −178.51 (13) |
C7—C8—C9—C10 | 0.7 (2) | C9—C1—C12—N1 | 1.58 (19) |
C11—C8—C9—C10 | −178.92 (13) | N1—C13—C14—C15 | 172.83 (13) |
C7—C8—C9—C1 | −179.71 (14) | C13—C14—C15—O3 | 70.40 (18) |
C11—C8—C9—C1 | 0.6 (2) | O2—C12—N1—C11 | 175.21 (14) |
C2—C1—C9—C8 | −179.73 (14) | C1—C12—N1—C11 | −4.5 (2) |
C12—C1—C9—C8 | 0.2 (2) | O2—C12—N1—C13 | −1.3 (2) |
C2—C1—C9—C10 | −0.2 (2) | C1—C12—N1—C13 | 179.01 (12) |
C12—C1—C9—C10 | 179.73 (13) | O1—C11—N1—C12 | −174.30 (14) |
C3—C4—C10—C9 | 0.0 (2) | C8—C11—N1—C12 | 5.3 (2) |
C3—C4—C10—C5 | −179.81 (14) | O1—C11—N1—C13 | 2.2 (2) |
C8—C9—C10—C4 | 179.99 (13) | C8—C11—N1—C13 | −178.21 (12) |
C1—C9—C10—C4 | 0.4 (2) | C14—C13—N1—C12 | 90.17 (16) |
C8—C9—C10—C5 | −0.2 (2) | C14—C13—N1—C11 | −86.61 (16) |
C1—C9—C10—C5 | −179.75 (13) | C14—C15—O3—C16 | 176.34 (14) |
C6—C5—C10—C4 | 179.26 (15) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.99 (1) | 2.37 (1) | 3.235 (2) | 145 (1) |
Symmetry code: (i) x, y−1, z. |