Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016611/ob6282sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016611/ob6282Isup2.hkl |
CCDC reference: 222843
The title compound was prepared via irradiation (with light of wavelength longer than 300 nm) of a benzene solution of N-methyl-1,8-naphthalenedicarboximide with 4-methoxyphenylacetylene, and isolated as one of the products of the photoreaction by flash column chromatography on silica gel (m.p. 441–442 K). Single crystals of (I) suitable for X-ray diffractionwere grown from an ethanol–ethyl acetate solution.
The positions of all H atoms were fixed geometrically and distances to H atoms were set by the program.
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. The crystal packing diagram of (I), viewed down the b axis. |
C22H17NO3 | F(000) = 720 |
Mr = 343.37 | Dx = 1.334 Mg m−3 |
Monoclinic, P21/c | Melting point = 441–442 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.893 (2) Å | Cell parameters from 28 reflections |
b = 14.248 (2) Å | θ = 2.8–14.4° |
c = 8.662 (1) Å | µ = 0.09 mm−1 |
β = 94.63 (1)° | T = 291 K |
V = 1709.0 (4) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.25 × 0.20 mm |
Siemens P4 diffractometer | Rint = 0.014 |
Radiation source: normal-focus sealed tube | θmax = 25.0°, θmin = 1.5° |
Graphite monochromator | h = −16→16 |
ω scans | k = −16→0 |
3489 measured reflections | l = 0→10 |
3016 independent reflections | 3 standard reflections every 97 reflections |
1944 reflections with I > 2σ(I) | intensity decay: 2.5% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0517P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
3016 reflections | Δρmax = 0.17 e Å−3 |
242 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXTL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0136 (14) |
C22H17NO3 | V = 1709.0 (4) Å3 |
Mr = 343.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.893 (2) Å | µ = 0.09 mm−1 |
b = 14.248 (2) Å | T = 291 K |
c = 8.662 (1) Å | 0.30 × 0.25 × 0.20 mm |
β = 94.63 (1)° |
Siemens P4 diffractometer | Rint = 0.014 |
3489 measured reflections | 3 standard reflections every 97 reflections |
3016 independent reflections | intensity decay: 2.5% |
1944 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 0.94 | Δρmax = 0.17 e Å−3 |
3016 reflections | Δρmin = −0.16 e Å−3 |
242 parameters |
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. The structure was solved by direct methods(Sheldrick, 1990) and successive difference Fourier syntheses. 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 | ||
O1 | 0.35318 (11) | 0.33848 (10) | 0.16333 (18) | 0.0622 (4) | |
O2 | 0.21426 (10) | 0.45414 (10) | 0.57923 (17) | 0.0566 (4) | |
O3 | −0.01553 (9) | 0.61083 (11) | −0.19819 (16) | 0.0592 (4) | |
N | 0.28310 (11) | 0.39476 (10) | 0.37173 (18) | 0.0425 (4) | |
C1 | 0.19369 (13) | 0.56770 (14) | 0.0802 (2) | 0.0439 (5) | |
H1 | 0.2534 | 0.5379 | 0.0863 | 0.053* | |
C2 | 0.13603 (12) | 0.56452 (13) | −0.0578 (2) | 0.0439 (5) | |
H2 | 0.1572 | 0.5330 | −0.1428 | 0.053* | |
C3 | 0.04745 (13) | 0.60811 (13) | −0.0690 (2) | 0.0422 (5) | |
C4 | 0.01673 (14) | 0.65462 (15) | 0.0587 (2) | 0.0506 (5) | |
H4 | −0.0432 | 0.6840 | 0.0521 | 0.061* | |
C5 | 0.07454 (13) | 0.65744 (14) | 0.1953 (2) | 0.0455 (5) | |
H5 | 0.0530 | 0.6889 | 0.2800 | 0.055* | |
C6 | 0.16485 (12) | 0.61400 (12) | 0.2092 (2) | 0.0370 (5) | |
C7 | 0.22323 (13) | 0.62185 (12) | 0.3571 (2) | 0.0390 (5) | |
C8 | 0.21981 (16) | 0.67888 (15) | 0.4772 (3) | 0.0525 (6) | |
C9 | 0.30349 (15) | 0.63629 (14) | 0.5740 (2) | 0.0484 (5) | |
H9 | 0.2859 | 0.6095 | 0.6720 | 0.058* | |
C10 | 0.30681 (13) | 0.56229 (13) | 0.4394 (2) | 0.0378 (5) | |
C11 | 0.40003 (12) | 0.55680 (12) | 0.3638 (2) | 0.0366 (4) | |
C12 | 0.46988 (14) | 0.62763 (13) | 0.3860 (2) | 0.0427 (5) | |
C13 | 0.45852 (16) | 0.70108 (14) | 0.5006 (2) | 0.0526 (6) | |
H13 | 0.5038 | 0.7492 | 0.5101 | 0.063* | |
C14 | 0.38680 (16) | 0.70196 (15) | 0.5913 (3) | 0.0563 (6) | |
H14 | 0.3884 | 0.7461 | 0.6705 | 0.068* | |
C15 | 0.55197 (14) | 0.62181 (15) | 0.3053 (2) | 0.0516 (6) | |
H15 | 0.5982 | 0.6690 | 0.3175 | 0.062* | |
C16 | 0.56663 (15) | 0.54765 (16) | 0.2075 (3) | 0.0557 (6) | |
H16 | 0.6214 | 0.5461 | 0.1525 | 0.067* | |
C17 | 0.50016 (14) | 0.47614 (15) | 0.1914 (2) | 0.0482 (5) | |
H17 | 0.5108 | 0.4251 | 0.1280 | 0.058* | |
C18 | 0.41687 (13) | 0.48051 (12) | 0.2704 (2) | 0.0387 (5) | |
C19 | 0.34958 (14) | 0.40037 (13) | 0.2600 (2) | 0.0424 (5) | |
C20 | 0.26616 (13) | 0.46691 (13) | 0.4748 (2) | 0.0413 (5) | |
C21 | 0.22993 (15) | 0.30613 (13) | 0.3835 (3) | 0.0608 (6) | |
H21A | 0.1868 | 0.2978 | 0.2923 | 0.073* | |
H21B | 0.1935 | 0.3080 | 0.4730 | 0.073* | |
H21C | 0.2748 | 0.2548 | 0.3929 | 0.073* | |
C22 | 0.01312 (16) | 0.56599 (18) | −0.3339 (2) | 0.0639 (6) | |
H22A | 0.0706 | 0.5953 | −0.3653 | 0.077* | |
H22B | −0.0376 | 0.5715 | −0.4154 | 0.077* | |
H22C | 0.0257 | 0.5008 | −0.3124 | 0.077* | |
H8 | 0.1820 (15) | 0.7324 (16) | 0.494 (2) | 0.073 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0683 (10) | 0.0456 (9) | 0.0718 (10) | 0.0030 (8) | −0.0009 (8) | −0.0206 (8) |
O2 | 0.0530 (9) | 0.0589 (10) | 0.0590 (9) | −0.0021 (7) | 0.0102 (8) | 0.0095 (8) |
O3 | 0.0444 (8) | 0.0814 (11) | 0.0495 (9) | 0.0060 (7) | −0.0114 (7) | −0.0040 (8) |
N | 0.0426 (9) | 0.0315 (9) | 0.0522 (10) | −0.0031 (7) | −0.0038 (8) | 0.0009 (8) |
C1 | 0.0392 (11) | 0.0441 (11) | 0.0474 (12) | 0.0087 (9) | −0.0027 (9) | −0.0004 (10) |
C2 | 0.0427 (11) | 0.0437 (11) | 0.0444 (11) | 0.0042 (9) | −0.0022 (9) | −0.0037 (10) |
C3 | 0.0359 (10) | 0.0445 (11) | 0.0448 (11) | −0.0026 (9) | −0.0060 (9) | 0.0040 (10) |
C4 | 0.0350 (10) | 0.0606 (14) | 0.0555 (13) | 0.0111 (10) | −0.0009 (10) | 0.0007 (12) |
C5 | 0.0432 (11) | 0.0478 (12) | 0.0455 (12) | 0.0078 (10) | 0.0029 (9) | −0.0022 (10) |
C6 | 0.0367 (10) | 0.0300 (10) | 0.0434 (11) | 0.0015 (8) | −0.0014 (9) | 0.0047 (9) |
C7 | 0.0401 (10) | 0.0336 (10) | 0.0424 (11) | 0.0026 (9) | −0.0027 (9) | −0.0001 (9) |
C8 | 0.0568 (13) | 0.0440 (13) | 0.0557 (14) | 0.0125 (11) | −0.0023 (11) | −0.0092 (11) |
C9 | 0.0582 (13) | 0.0451 (12) | 0.0407 (11) | 0.0039 (10) | −0.0034 (10) | −0.0064 (9) |
C10 | 0.0427 (11) | 0.0319 (10) | 0.0374 (10) | 0.0013 (8) | −0.0054 (8) | −0.0001 (9) |
C11 | 0.0389 (10) | 0.0337 (10) | 0.0353 (10) | 0.0028 (8) | −0.0090 (8) | 0.0036 (9) |
C12 | 0.0453 (11) | 0.0365 (11) | 0.0435 (11) | −0.0013 (9) | −0.0128 (9) | 0.0104 (9) |
C13 | 0.0589 (13) | 0.0370 (12) | 0.0583 (14) | −0.0074 (10) | −0.0188 (12) | 0.0023 (11) |
C14 | 0.0707 (15) | 0.0428 (12) | 0.0515 (13) | 0.0002 (11) | −0.0185 (12) | −0.0120 (10) |
C15 | 0.0433 (12) | 0.0520 (13) | 0.0574 (14) | −0.0082 (10) | −0.0094 (11) | 0.0183 (11) |
C16 | 0.0421 (12) | 0.0693 (16) | 0.0554 (13) | 0.0010 (11) | 0.0024 (10) | 0.0154 (13) |
C17 | 0.0487 (12) | 0.0522 (13) | 0.0430 (12) | 0.0090 (10) | 0.0004 (10) | 0.0024 (10) |
C18 | 0.0402 (10) | 0.0370 (11) | 0.0374 (10) | 0.0044 (9) | −0.0063 (9) | 0.0024 (9) |
C19 | 0.0428 (11) | 0.0344 (11) | 0.0479 (12) | 0.0083 (9) | −0.0097 (10) | 0.0002 (10) |
C20 | 0.0369 (10) | 0.0421 (11) | 0.0432 (11) | 0.0024 (9) | −0.0074 (9) | 0.0047 (10) |
C21 | 0.0558 (13) | 0.0396 (12) | 0.0860 (17) | −0.0095 (10) | −0.0014 (12) | 0.0053 (12) |
C22 | 0.0580 (14) | 0.0821 (17) | 0.0494 (13) | −0.0022 (13) | −0.0093 (11) | −0.0033 (13) |
O1—C19 | 1.220 (2) | C9—H9 | 0.9800 |
O2—C20 | 1.215 (2) | C10—C11 | 1.499 (3) |
O3—C3 | 1.364 (2) | C10—C20 | 1.513 (3) |
O3—C22 | 1.423 (2) | C11—C18 | 1.386 (2) |
N—C19 | 1.393 (2) | C11—C12 | 1.403 (2) |
N—C20 | 1.394 (2) | C12—C15 | 1.387 (3) |
N—C21 | 1.471 (2) | C12—C13 | 1.460 (3) |
C1—C2 | 1.385 (2) | C13—C14 | 1.318 (3) |
C1—C6 | 1.385 (2) | C13—H13 | 0.9300 |
C1—H1 | 0.9300 | C14—H14 | 0.9300 |
C2—C3 | 1.375 (2) | C15—C16 | 1.380 (3) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.386 (3) | C16—C17 | 1.375 (3) |
C4—C5 | 1.376 (3) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—C18 | 1.393 (3) |
C5—C6 | 1.396 (2) | C17—H17 | 0.9300 |
C5—H5 | 0.9300 | C18—C19 | 1.474 (3) |
C6—C7 | 1.464 (2) | C21—H21A | 0.9600 |
C7—C8 | 1.323 (3) | C21—H21B | 0.9600 |
C7—C10 | 1.563 (2) | C21—H21C | 0.9600 |
C8—C9 | 1.505 (3) | C22—H22A | 0.9600 |
C8—H8 | 0.94 (2) | C22—H22B | 0.9600 |
C9—C14 | 1.486 (3) | C22—H22C | 0.9600 |
C9—C10 | 1.576 (2) | ||
C3—O3—C22 | 117.47 (15) | C18—C11—C10 | 119.21 (16) |
C19—N—C20 | 123.94 (16) | C12—C11—C10 | 121.00 (17) |
C19—N—C21 | 117.54 (17) | C15—C12—C11 | 118.40 (19) |
C20—N—C21 | 118.49 (17) | C15—C12—C13 | 121.59 (19) |
C2—C1—C6 | 121.83 (17) | C11—C12—C13 | 119.84 (19) |
C2—C1—H1 | 119.1 | C14—C13—C12 | 122.7 (2) |
C6—C1—H1 | 119.1 | C14—C13—H13 | 118.6 |
C3—C2—C1 | 119.88 (18) | C12—C13—H13 | 118.6 |
C3—C2—H2 | 120.1 | C13—C14—C9 | 123.65 (19) |
C1—C2—H2 | 120.1 | C13—C14—H14 | 118.2 |
O3—C3—C2 | 125.57 (18) | C9—C14—H14 | 118.2 |
O3—C3—C4 | 115.01 (17) | C16—C15—C12 | 121.6 (2) |
C2—C3—C4 | 119.43 (18) | C16—C15—H15 | 119.2 |
C5—C4—C3 | 120.27 (18) | C12—C15—H15 | 119.2 |
C5—C4—H4 | 119.9 | C17—C16—C15 | 119.9 (2) |
C3—C4—H4 | 119.9 | C17—C16—H16 | 120.1 |
C4—C5—C6 | 121.33 (19) | C15—C16—H16 | 120.1 |
C4—C5—H5 | 119.3 | C16—C17—C18 | 119.68 (19) |
C6—C5—H5 | 119.3 | C16—C17—H17 | 120.2 |
C1—C6—C5 | 117.27 (17) | C18—C17—H17 | 120.2 |
C1—C6—C7 | 124.53 (16) | C11—C18—C17 | 120.54 (18) |
C5—C6—C7 | 118.19 (17) | C11—C18—C19 | 120.47 (17) |
C8—C7—C6 | 132.98 (18) | C17—C18—C19 | 118.91 (17) |
C8—C7—C10 | 92.74 (16) | O1—C19—N | 120.11 (18) |
C6—C7—C10 | 134.11 (16) | O1—C19—C18 | 122.75 (19) |
C7—C8—C9 | 96.60 (17) | N—C19—C18 | 117.06 (17) |
C7—C8—H8 | 132.1 (13) | O2—C20—N | 120.49 (18) |
C9—C8—H8 | 131.0 (13) | O2—C20—C10 | 122.65 (18) |
C14—C9—C8 | 111.26 (17) | N—C20—C10 | 116.56 (17) |
C14—C9—C10 | 115.26 (17) | N—C21—H21A | 109.5 |
C8—C9—C10 | 85.70 (14) | N—C21—H21B | 109.5 |
C14—C9—H9 | 113.9 | H21A—C21—H21B | 109.5 |
C8—C9—H9 | 113.9 | N—C21—H21C | 109.5 |
C10—C9—H9 | 113.9 | H21A—C21—H21C | 109.5 |
C11—C10—C20 | 113.05 (15) | H21B—C21—H21C | 109.5 |
C11—C10—C7 | 117.76 (15) | O3—C22—H22A | 109.5 |
C20—C10—C7 | 107.73 (14) | O3—C22—H22B | 109.5 |
C11—C10—C9 | 115.83 (15) | H22A—C22—H22B | 109.5 |
C20—C10—C9 | 114.65 (15) | O3—C22—H22C | 109.5 |
C7—C10—C9 | 84.77 (13) | H22A—C22—H22C | 109.5 |
C18—C11—C12 | 119.79 (18) | H22B—C22—H22C | 109.5 |
C6—C1—C2—C3 | 0.0 (3) | C18—C11—C12—C15 | 3.9 (3) |
C22—O3—C3—C2 | −0.9 (3) | C10—C11—C12—C15 | −175.90 (16) |
C22—O3—C3—C4 | 178.66 (19) | C18—C11—C12—C13 | −171.50 (16) |
C1—C2—C3—O3 | 179.38 (18) | C10—C11—C12—C13 | 8.7 (2) |
C1—C2—C3—C4 | −0.2 (3) | C15—C12—C13—C14 | −172.00 (19) |
O3—C3—C4—C5 | −179.38 (18) | C11—C12—C13—C14 | 3.3 (3) |
C2—C3—C4—C5 | 0.2 (3) | C12—C13—C14—C9 | −8.1 (3) |
C3—C4—C5—C6 | 0.0 (3) | C8—C9—C14—C13 | −94.3 (2) |
C2—C1—C6—C5 | 0.3 (3) | C10—C9—C14—C13 | 1.1 (3) |
C2—C1—C6—C7 | −178.50 (18) | C11—C12—C15—C16 | −1.3 (3) |
C4—C5—C6—C1 | −0.2 (3) | C13—C12—C15—C16 | 174.04 (17) |
C4—C5—C6—C7 | 178.61 (18) | C12—C15—C16—C17 | −1.7 (3) |
C1—C6—C7—C8 | 161.4 (2) | C15—C16—C17—C18 | 2.0 (3) |
C5—C6—C7—C8 | −17.3 (3) | C12—C11—C18—C17 | −3.7 (3) |
C1—C6—C7—C10 | −24.6 (3) | C10—C11—C18—C17 | 176.16 (15) |
C5—C6—C7—C10 | 156.70 (19) | C12—C11—C18—C19 | 172.96 (16) |
C6—C7—C8—C9 | 179.2 (2) | C10—C11—C18—C19 | −7.2 (2) |
C10—C7—C8—C9 | 3.48 (16) | C16—C17—C18—C11 | 0.7 (3) |
C7—C8—C9—C14 | 112.0 (2) | C16—C17—C18—C19 | −175.99 (17) |
C7—C8—C9—C10 | −3.45 (16) | C20—N—C19—O1 | −172.21 (16) |
C8—C7—C10—C11 | −119.82 (18) | C21—N—C19—O1 | 9.6 (3) |
C6—C7—C10—C11 | 64.6 (3) | C20—N—C19—C18 | 10.9 (2) |
C8—C7—C10—C20 | 110.92 (17) | C21—N—C19—C18 | −167.30 (16) |
C6—C7—C10—C20 | −64.7 (3) | C11—C18—C19—O1 | 168.93 (17) |
C8—C7—C10—C9 | −3.31 (16) | C17—C18—C19—O1 | −14.4 (3) |
C6—C7—C10—C9 | −178.9 (2) | C11—C18—C19—N | −14.3 (2) |
C14—C9—C10—C11 | 9.8 (2) | C17—C18—C19—N | 162.37 (16) |
C8—C9—C10—C11 | 121.29 (17) | C19—N—C20—O2 | −172.68 (17) |
C14—C9—C10—C20 | 144.29 (17) | C21—N—C20—O2 | 5.5 (3) |
C8—C9—C10—C20 | −104.21 (17) | C19—N—C20—C10 | 13.4 (2) |
C14—C9—C10—C7 | −108.58 (17) | C21—N—C20—C10 | −168.38 (16) |
C8—C9—C10—C7 | 2.92 (14) | C11—C10—C20—O2 | 153.14 (17) |
C20—C10—C11—C18 | 30.3 (2) | C7—C10—C20—O2 | −75.0 (2) |
C7—C10—C11—C18 | −96.4 (2) | C9—C10—C20—O2 | 17.4 (2) |
C9—C10—C11—C18 | 165.49 (15) | C11—C10—C20—N | −33.1 (2) |
C20—C10—C11—C12 | −149.91 (16) | C7—C10—C20—N | 98.76 (17) |
C7—C10—C11—C12 | 83.4 (2) | C9—C10—C20—N | −168.86 (15) |
C9—C10—C11—C12 | −14.7 (2) |
Experimental details
Crystal data | |
Chemical formula | C22H17NO3 |
Mr | 343.37 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 13.893 (2), 14.248 (2), 8.662 (1) |
β (°) | 94.63 (1) |
V (Å3) | 1709.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.30 × 0.25 × 0.20 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3489, 3016, 1944 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.101, 0.94 |
No. of reflections | 3016 |
No. of parameters | 242 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.16 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SHELXTL (Sheldrick, 1997), SHELXTL.
C7—C8 | 1.323 (3) | C10—C11 | 1.499 (3) |
C7—C10 | 1.563 (2) | C11—C12 | 1.403 (2) |
C8—C9 | 1.505 (3) | C12—C13 | 1.460 (3) |
C9—C14 | 1.486 (3) | C13—C14 | 1.318 (3) |
C9—C10 | 1.576 (2) | ||
C8—C7—C10 | 92.74 (16) | C11—C10—C7 | 117.76 (15) |
C6—C7—C10 | 134.11 (16) | C20—C10—C7 | 107.73 (14) |
C7—C8—C9 | 96.60 (17) | C11—C10—C9 | 115.83 (15) |
C8—C9—C10 | 85.70 (14) | C7—C10—C9 | 84.77 (13) |
C22—O3—C3—C2 | −0.9 (3) | C6—C7—C10—C20 | −64.7 (3) |
C1—C6—C7—C10 | −24.6 (3) | C8—C9—C10—C20 | −104.21 (17) |
C10—C7—C8—C9 | 3.48 (16) | C8—C9—C10—C7 | 2.92 (14) |
C8—C7—C10—C11 | −119.82 (18) | C8—C9—C14—C13 | −94.3 (2) |
The photochemistry of imides with alkenes has been extensively studied (Kanaoka, 1978; Mazzocchi, 1981). As part of our studies on the photoinduced electron-transfer reactions of aromatic imides with various organic electron donors (Xue et al., 2000), we have investigated the photoinduced reactions of naphthalimides with alkynes. We report here the X-ray crystal structure of the title compound, (I), which is one of the products of the photoreaction of N-methyl-1,8-naphthalenedicarboximide with 4-methoxyphenylacetylene.
The bond lengths and angles in (I) show normal values, except for the geometry of the cyclobutene ring (Fig. 1 and Table 1). The C7—C10 bond is elongated by the steric effect of the bulky substituents attached at atoms C7 and C10. This C7—C10 bond distance of 1.563 (2) Å is slightly longer than that of 4-methyl-2-phenylbenzo[de]cyclobut[i]isoquinoline-3,5(2H)-dione (Liu, Shi et al., 2003), but is much like that of 9,10-epoxy-4-methyl-2-phenylbenzo[de]cyclobut[i]isoquinoline-3,5(2H)-dione (Liu, Li et al., 2003). Such an elongation has also been found in another cyclobutene derivative (Usman et al., 2001).
The naphthalimide moiety has lost the coplanarity due to the sp3 character of atoms C9 and C10. The C7–C10 planar cyclobutene ring makes dihedral angles of 68.86 (8), 70.36 (8) and 83.03 (7)°, with the mean planes of the C9–C14 cyclohexadiene ring, the C11—C12/C15—C18 benzene ring and the C10–C11/C18–C20/N ring, respectively. The C9–C14 cyclohexadiene ring forms dihedral angles of 7.84 (11) and 17.50 (9)°, respectively, with the C11—C12/C15—C18 benzene ring and the C10—C11/C18—C20/N ring, while these two rings have a dihedral angle of 12.88 (10)°. The C1–C6 phenyl ring is twisted by 21.15 (14)° with respect to the cyclobutene ring.
In the crystal packing of (I) (Fig. 2), the molecules are arranged along the b axis into parallel infinite stripes in which the molecules orientate head-to-head and the two neighbouring tetrahydronaphthalene moieties lie back-to-back and the other two phenyl rings overlap face-to-face. Such arrangements take advantage of the π–π-stacking interactions involving these aromatic rings, which stabilize the crystal packing.