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In the title compound, C16H15NO3, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003428/su6012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003428/su6012Isup2.hkl
Contains datablock I

CCDC reference: 206783

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](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








Computing details top

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).

(I) top
Crystal data top
C16H15NO3Z = 2
Mr = 269.29F(000) = 284
Triclinic, P1Dx = 1.341 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.154 (1) ÅCell parameters from 3178 reflections
b = 9.554 (2) Åθ = 4.2–28°
c = 9.866 (2) ŵ = 0.09 mm1
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 tubeRint = 0.028
Graphite monochromatorθmax = 28°, θmin = 3.6°
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm-1h = 89
ω scansk = 1312
5193 measured reflectionsl = 1213
3174 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100All 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 parametersΔρmax = 0.36 e Å3
0 restraintsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
C10.25298 (19)0.02757 (14)0.01213 (15)0.0143 (3)
C20.2216 (2)0.07602 (16)0.11934 (15)0.0182 (3)
C30.1964 (2)0.02066 (17)0.21608 (16)0.0209 (4)
C40.2002 (2)0.16262 (17)0.17950 (16)0.0199 (3)
C50.2368 (2)0.36343 (16)0.00312 (17)0.0233 (4)
C60.2693 (2)0.41003 (17)0.12714 (18)0.0261 (4)
C70.2959 (2)0.31309 (16)0.22294 (18)0.0218 (4)
C80.2900 (2)0.16961 (15)0.18657 (15)0.0160 (3)
C90.25867 (19)0.11916 (15)0.05160 (15)0.0146 (3)
C100.2311 (2)0.21693 (16)0.04561 (16)0.0182 (3)
C110.3153 (2)0.06950 (15)0.28878 (15)0.0169 (3)
C120.2805 (2)0.12986 (15)0.11250 (15)0.0149 (3)
C130.3474 (2)0.17507 (16)0.34449 (16)0.0173 (3)
C140.1593 (2)0.21222 (18)0.42944 (16)0.0205 (3)
C150.1881 (3)0.30030 (16)0.54574 (17)0.0219 (4)
C160.2651 (3)0.52593 (19)0.59851 (18)0.0270 (4)
N10.31637 (16)0.07483 (12)0.24347 (12)0.0151 (3)
O10.33382 (16)0.10754 (11)0.40880 (11)0.0249 (3)
O20.27231 (15)0.25762 (10)0.08492 (11)0.0218 (3)
O30.24875 (16)0.43908 (11)0.49050 (11)0.0238 (3)
H20.219 (2)0.1770 (18)0.1424 (16)0.029*
H30.177 (2)0.0138 (17)0.3097 (17)0.029*
H40.183 (2)0.2281 (17)0.2463 (17)0.029*
H50.221 (2)0.4281 (17)0.0727 (17)0.029*
H60.272 (2)0.5115 (18)0.1567 (16)0.029*
H70.316 (2)0.3443 (17)0.3115 (18)0.029*
H13A0.410 (2)0.2593 (18)0.2948 (17)0.029*
H14A0.077 (2)0.2629 (17)0.3700 (16)0.029*
H15A0.067 (2)0.3068 (17)0.6098 (17)0.029*
H16A0.310 (2)0.622 (2)0.5567 (18)0.036*
H13B0.439 (2)0.1303 (17)0.4038 (17)0.029*
H14B0.088 (2)0.1209 (18)0.4688 (17)0.029*
H15B0.293 (2)0.2580 (17)0.6005 (17)0.029*
H16B0.137 (3)0.5277 (17)0.6644 (18)0.036*
H16C0.367 (3)0.4966 (18)0.6551 (18)0.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0123 (7)0.0146 (7)0.0156 (7)0.0001 (6)0.0001 (6)0.0005 (6)
C20.0165 (8)0.0191 (8)0.0183 (8)0.0009 (6)0.0002 (6)0.0004 (6)
C30.0184 (8)0.0280 (9)0.0164 (8)0.0014 (7)0.0026 (6)0.0029 (7)
C40.0151 (8)0.0243 (8)0.0211 (9)0.0008 (7)0.0007 (6)0.0101 (7)
C50.0227 (9)0.0169 (8)0.0310 (10)0.0019 (7)0.0014 (7)0.0096 (7)
C60.0307 (10)0.0122 (7)0.0344 (10)0.0011 (7)0.0007 (8)0.0018 (7)
C70.0230 (9)0.0166 (8)0.0251 (9)0.0018 (7)0.0034 (7)0.0028 (7)
C80.0146 (8)0.0136 (7)0.0192 (8)0.0005 (6)0.0001 (6)0.0010 (6)
C90.0103 (7)0.0143 (7)0.0189 (8)0.0003 (6)0.0008 (6)0.0027 (6)
C100.0135 (8)0.0188 (8)0.0224 (8)0.0016 (6)0.0010 (6)0.0056 (6)
C110.0161 (8)0.0160 (7)0.0180 (8)0.0004 (6)0.0009 (6)0.0001 (6)
C120.0136 (7)0.0156 (7)0.0150 (8)0.0001 (6)0.0004 (6)0.0007 (6)
C130.0204 (8)0.0159 (7)0.0166 (8)0.0008 (6)0.0052 (6)0.0031 (6)
C140.0209 (9)0.0214 (8)0.0191 (9)0.0006 (7)0.0011 (7)0.0033 (7)
C150.0263 (9)0.0198 (8)0.0185 (8)0.0004 (7)0.0028 (7)0.0027 (7)
C160.0356 (11)0.0222 (9)0.0239 (9)0.0005 (8)0.0028 (8)0.0066 (7)
N10.0179 (7)0.0119 (6)0.0160 (7)0.0017 (5)0.0043 (5)0.0017 (5)
O10.0343 (7)0.0218 (6)0.0189 (6)0.0018 (5)0.0078 (5)0.0020 (5)
O20.0287 (6)0.0134 (5)0.0232 (6)0.0009 (5)0.0047 (5)0.0004 (4)
O30.0366 (7)0.0175 (6)0.0172 (6)0.0002 (5)0.0012 (5)0.0034 (4)
Geometric parameters (Å, º) top
C1—C21.385 (2)C11—O11.2324 (17)
C1—C91.425 (2)C11—N11.413 (2)
C1—C121.478 (2)C12—O21.2310 (17)
C2—C31.410 (2)C12—N11.407 (2)
C2—H20.973 (17)C13—N11.4750 (18)
C3—C41.375 (2)C13—C141.550 (2)
C3—H30.981 (17)C13—H13A0.987 (17)
C4—C101.422 (2)C13—H13B1.002 (16)
C4—H40.965 (16)C14—C151.513 (2)
C5—C61.372 (2)C14—H14A0.978 (16)
C5—C101.429 (2)C14—H14B1.037 (17)
C5—H50.978 (16)C15—O31.4402 (19)
C6—C71.407 (2)C15—H15A1.014 (17)
C6—H60.990 (17)C15—H15B1.041 (17)
C7—C81.390 (2)C16—O31.4199 (19)
C7—H70.928 (17)C16—H16A1.008 (18)
C8—C91.422 (2)C16—H16B1.054 (18)
C8—C111.474 (2)C16—H16C0.996 (18)
C9—C101.424 (2)
C2—C1—C9120.87 (13)N1—C11—C8116.8 (1)
C2—C1—C12119.34 (13)O2—C12—N1120.6 (1)
C9—C1—C12119.79 (13)O2—C12—C1122.4 (1)
C1—C2—C3119.78 (14)N1—C12—C1116.9 (1)
C1—C2—H2118.5 (10)N1—C13—C14111.00 (12)
C3—C2—H2121.8 (10)N1—C13—H13A108.2 (10)
C4—C3—C2120.13 (15)C14—C13—H13A111.7 (10)
C4—C3—H3120.2 (9)N1—C13—H13B106.9 (9)
C2—C3—H3119.7 (9)C14—C13—H13B111.9 (9)
C3—C4—C10121.97 (14)H13A—C13—H13B106.8 (13)
C3—C4—H4119.6 (10)C15—C14—C13112.47 (13)
C10—C4—H4118.4 (10)C15—C14—H14A109.0 (9)
C6—C5—C10121.46 (15)C13—C14—H14A109.9 (10)
C6—C5—H5122.1 (10)C15—C14—H14B109.3 (9)
C10—C5—H5116.4 (10)C13—C14—H14B109.9 (9)
C5—C6—C7120.13 (15)H14A—C14—H14B106.1 (13)
C5—C6—H6121.3 (10)O3—C15—C14109.31 (13)
C7—C6—H6118.5 (10)O3—C15—H15A109.5 (9)
C8—C7—C6120.43 (16)C14—C15—H15A110.4 (9)
C8—C7—H7119.2 (10)O3—C15—H15B107.1 (9)
C6—C7—H7120.3 (10)C14—C15—H15B110.8 (9)
C7—C8—C9120.32 (14)H15A—C15—H15B109.5 (13)
C7—C8—C11119.73 (14)O3—C16—H16A108.2 (10)
C9—C8—C11119.95 (13)O3—C16—H16B110.7 (9)
C8—C9—C10119.44 (13)H16A—C16—H16B113.8 (14)
C8—C9—C1121.16 (13)O3—C16—H16C113.8 (10)
C10—C9—C1119.39 (14)H16A—C16—H16C102.3 (14)
C4—C10—C9117.85 (14)H16B—C16—H16C107.9 (14)
C4—C10—C5123.92 (14)C12—N1—C11125.13 (12)
C9—C10—C5118.22 (14)C12—N1—C13117.81 (12)
O1—C11—N1120.5 (1)C11—N1—C13116.97 (12)
O1—C11—C8122.5 (1)C16—O3—C15110.10 (12)
C9—C1—C2—C30.5 (2)C6—C5—C10—C90.5 (2)
C12—C1—C2—C3179.59 (14)C7—C8—C11—O13.2 (2)
C1—C2—C3—C40.9 (2)C9—C8—C11—O1176.42 (14)
C2—C3—C4—C100.7 (2)C7—C8—C11—N1177.19 (13)
C10—C5—C6—C70.7 (2)C9—C8—C11—N13.1 (2)
C5—C6—C7—C80.2 (2)C2—C1—C12—O21.8 (2)
C6—C7—C8—C90.6 (2)C9—C1—C12—O2178.13 (14)
C6—C7—C8—C11179.09 (14)C2—C1—C12—N1178.51 (13)
C7—C8—C9—C100.7 (2)C9—C1—C12—N11.58 (19)
C11—C8—C9—C10178.92 (13)N1—C13—C14—C15172.83 (13)
C7—C8—C9—C1179.71 (14)C13—C14—C15—O370.40 (18)
C11—C8—C9—C10.6 (2)O2—C12—N1—C11175.21 (14)
C2—C1—C9—C8179.73 (14)C1—C12—N1—C114.5 (2)
C12—C1—C9—C80.2 (2)O2—C12—N1—C131.3 (2)
C2—C1—C9—C100.2 (2)C1—C12—N1—C13179.01 (12)
C12—C1—C9—C10179.73 (13)O1—C11—N1—C12174.30 (14)
C3—C4—C10—C90.0 (2)C8—C11—N1—C125.3 (2)
C3—C4—C10—C5179.81 (14)O1—C11—N1—C132.2 (2)
C8—C9—C10—C4179.99 (13)C8—C11—N1—C13178.21 (12)
C1—C9—C10—C40.4 (2)C14—C13—N1—C1290.17 (16)
C8—C9—C10—C50.2 (2)C14—C13—N1—C1186.61 (16)
C1—C9—C10—C5179.75 (13)C14—C15—O3—C16176.34 (14)
C6—C5—C10—C4179.26 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.99 (1)2.37 (1)3.235 (2)145 (1)
Symmetry code: (i) x, y1, z.
 

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