Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022568/sj2314sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022568/sj2314Isup2.hkl |
CCDC reference: 600353
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.058
- wR factor = 0.123
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C11 = ... S PLAT793_ALERT_1_G Check the Absolute Configuration of C12 = ... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, (I), was prepared by irradiation of a benzene (150 ml) solution of N-methylnaphthalene-2,3-dicarboximide (633 mg, 3.0 mmol) with diphenylacetylene (1.068 g, 6 mmol) with UV light of wavelength longer than 300 nm purged with nitrogen, and isolated by flash column chromatography on silica gel, eluting with petroleum-ethyl acetate (4:1 v/v). Single crystals (m.p. 505–506 K) suitable for X-ray diffraction were obtained by recrystallization from ethanol-ethyl acetate solution (1:95 v/v).
Hydrogen atoms were placed in geometrically idealized positions and refined using a riding model with d (C—H) = 0.93 Å, Uiso =1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH and 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms.
In the studies of photochemistry of naphthalenedicarboximides with alkynes, it has been found that the photoinduced cycloadditions of N-methyl-1,8-naphthalenedicarboximides (NI18) with alkynes followed the pathway of NI18 with alkenes (Liu et al., 2006), but that is not the case for N-methylnaphthalene-2,3-dicarboximide (NI23). UV irradiation of NI23 in the presence of diphenylacetylene in benzene solution resulted in the novel adduct (I) and its structure is reported here (Figure 1).
The bond lengths and angles in (I) show normal values except for the geometry of the cyclobutene ring (Table 1). The C20—C21 bond length of 1.345 (3)Å is nearly the same as that in 4-methyl-1,2-diphenylbenzo[de]cyclobut[i]isoquinoline- 3,5(2H)-dione(1.346 (3) Å) (Liu et al., 2006), but is longer than those of 4,5,9,10-tetrahydro-4- methyl-2-phenyl-9,10-epoxy-3H,10aH-cyclobuta[benzo[2,3,4-de]- isoquinoline-3,5-dione (1.324 (2) Å) (Liu et al., 2003), Such elongation is considered to be caused by the steric effect of the bulky phenyl substituents on C20 and C21, respectively. The cyclobutene ring in the molecule is almost perpendicular to the plane of dihydronaphthalimide, the interplanar angle between the cyclobutene ring and the plane through the two six membered rings of the naphthalimide is 70.66 (9). The interplanar angle between the two benzene substituents on the cyclobutene ring is 42.47 (8).
For information on the photochemistry of naphthalenedicarboximides with alkynes see Liu et al. (2006) and for related structures see Liu et al. (2003, 2006).
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I) with the atom-numbering scheme and ellipsoids drawn at the 30% probability level. | |
Fig. 2. The formation of (I). |
C27H19NO2 | F(000) = 816 |
Mr = 389.43 | Dx = 1.293 Mg m−3 |
Monoclinic, P21/c | Melting point: 505 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.763 (2) Å | Cell parameters from 1602 reflections |
b = 7.9925 (15) Å | θ = 2.4–20.9° |
c = 23.438 (5) Å | µ = 0.08 mm−1 |
β = 97.326 (3)° | T = 298 K |
V = 1999.8 (7) Å3 | Plate, colourless |
Z = 4 | 0.28 × 0.22 × 0.08 mm |
Bruker SMART APEX CCD area-detector diffractometer | 2456 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 25.5°, θmin = 1.9° |
φ and ω scans | h = −11→13 |
10516 measured reflections | k = −9→7 |
3715 independent reflections | l = −28→24 |
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)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0426P)2] where P = (Fo2 + 2Fc2)/3 |
3715 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.15 e Å−3 |
C27H19NO2 | V = 1999.8 (7) Å3 |
Mr = 389.43 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.763 (2) Å | µ = 0.08 mm−1 |
b = 7.9925 (15) Å | T = 298 K |
c = 23.438 (5) Å | 0.28 × 0.22 × 0.08 mm |
β = 97.326 (3)° |
Bruker SMART APEX CCD area-detector diffractometer | 2456 reflections with I > 2σ(I) |
10516 measured reflections | Rint = 0.062 |
3715 independent reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.17 e Å−3 |
3715 reflections | Δρmin = −0.15 e Å−3 |
272 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 estimating e.s.d.'s involving l.s.planes. |
Refinement. Refinement of F2against 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 | ||
C1 | 0.5270 (3) | 0.7812 (4) | 0.55850 (12) | 0.0659 (9) | |
H1A | 0.5237 | 0.7875 | 0.5174 | 0.099* | |
H1B | 0.6028 | 0.7257 | 0.5743 | 0.099* | |
H1C | 0.5256 | 0.8921 | 0.5741 | 0.099* | |
C2 | 0.4147 (2) | 0.5119 (3) | 0.57395 (9) | 0.0415 (6) | |
C3 | 0.2884 (2) | 0.4690 (3) | 0.58640 (9) | 0.0362 (6) | |
C4 | 0.2254 (2) | 0.3278 (3) | 0.57293 (9) | 0.0417 (6) | |
H4 | 0.2692 | 0.2324 | 0.5647 | 0.050* | |
C5 | 0.0900 (2) | 0.3192 (3) | 0.57082 (9) | 0.0406 (6) | |
C6 | 0.0276 (3) | 0.1680 (3) | 0.55931 (10) | 0.0528 (7) | |
H6 | 0.0738 | 0.0705 | 0.5568 | 0.063* | |
C7 | −0.1008 (3) | 0.1601 (4) | 0.55158 (11) | 0.0608 (8) | |
H7 | −0.1408 | 0.0576 | 0.5448 | 0.073* | |
C8 | −0.1705 (3) | 0.3042 (4) | 0.55384 (11) | 0.0577 (8) | |
H8 | −0.2576 | 0.3000 | 0.5480 | 0.069* | |
C9 | −0.1089 (2) | 0.4554 (4) | 0.56487 (10) | 0.0501 (7) | |
H9 | −0.1560 | 0.5526 | 0.5658 | 0.060* | |
C10 | 0.0197 (2) | 0.4662 (3) | 0.57446 (9) | 0.0389 (6) | |
C11 | 0.0817 (2) | 0.6310 (3) | 0.59191 (10) | 0.0384 (6) | |
H11 | 0.0499 | 0.7255 | 0.5677 | 0.046* | |
C12 | 0.2275 (2) | 0.6241 (3) | 0.60469 (9) | 0.0361 (6) | |
C13 | 0.3101 (2) | 0.7618 (3) | 0.58514 (10) | 0.0428 (6) | |
C14 | 0.4107 (2) | 0.5646 (3) | 0.72463 (10) | 0.0410 (6) | |
H14 | 0.4304 | 0.5042 | 0.6931 | 0.049* | |
C15 | 0.4926 (2) | 0.5629 (3) | 0.77487 (11) | 0.0477 (7) | |
H15 | 0.5656 | 0.4997 | 0.7773 | 0.057* | |
C16 | 0.4659 (2) | 0.6550 (3) | 0.82139 (11) | 0.0506 (7) | |
H16 | 0.5206 | 0.6538 | 0.8555 | 0.061* | |
C17 | 0.3578 (2) | 0.7489 (3) | 0.81730 (11) | 0.0496 (7) | |
H17 | 0.3406 | 0.8131 | 0.8484 | 0.060* | |
C18 | 0.2754 (2) | 0.7483 (3) | 0.76758 (10) | 0.0435 (6) | |
H18 | 0.2023 | 0.8114 | 0.7655 | 0.052* | |
C19 | 0.2998 (2) | 0.6539 (3) | 0.71998 (9) | 0.0342 (6) | |
C20 | 0.2084 (2) | 0.6472 (3) | 0.66827 (10) | 0.0360 (6) | |
C21 | 0.0834 (2) | 0.6619 (3) | 0.65621 (10) | 0.0373 (6) | |
C22 | −0.0208 (2) | 0.6824 (3) | 0.69000 (10) | 0.0386 (6) | |
C23 | −0.0146 (2) | 0.6137 (3) | 0.74466 (11) | 0.0475 (7) | |
H23 | 0.0551 | 0.5512 | 0.7594 | 0.057* | |
C24 | −0.1108 (3) | 0.6373 (3) | 0.77724 (12) | 0.0585 (8) | |
H24 | −0.1054 | 0.5916 | 0.8140 | 0.070* | |
C25 | −0.2141 (3) | 0.7276 (4) | 0.75599 (15) | 0.0628 (9) | |
H25 | −0.2781 | 0.7451 | 0.7785 | 0.075* | |
C26 | −0.2234 (3) | 0.7922 (4) | 0.70151 (15) | 0.0635 (9) | |
H26 | −0.2948 | 0.8510 | 0.6866 | 0.076* | |
C27 | −0.1271 (2) | 0.7703 (3) | 0.66871 (12) | 0.0521 (7) | |
H27 | −0.1338 | 0.8152 | 0.6318 | 0.062* | |
N1 | 0.41972 (19) | 0.6876 (3) | 0.57308 (8) | 0.0442 (5) | |
O1 | 0.50087 (17) | 0.4229 (2) | 0.56464 (7) | 0.0553 (5) | |
O2 | 0.28991 (17) | 0.9106 (2) | 0.58275 (8) | 0.0599 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.056 (2) | 0.076 (2) | 0.068 (2) | −0.0136 (16) | 0.0180 (15) | −0.0095 (16) |
C2 | 0.0456 (17) | 0.0540 (18) | 0.0244 (13) | 0.0114 (13) | 0.0026 (11) | 0.0012 (12) |
C3 | 0.0397 (15) | 0.0406 (15) | 0.0282 (13) | 0.0099 (12) | 0.0038 (11) | 0.0018 (11) |
C4 | 0.0517 (18) | 0.0376 (15) | 0.0352 (14) | 0.0127 (13) | 0.0033 (12) | 0.0013 (12) |
C5 | 0.0518 (17) | 0.0427 (16) | 0.0270 (13) | 0.0008 (13) | 0.0044 (11) | 0.0015 (12) |
C6 | 0.066 (2) | 0.0465 (17) | 0.0441 (17) | −0.0019 (15) | 0.0011 (14) | −0.0001 (13) |
C7 | 0.074 (2) | 0.062 (2) | 0.0461 (17) | −0.0197 (17) | 0.0068 (15) | −0.0055 (15) |
C8 | 0.0507 (18) | 0.082 (2) | 0.0396 (16) | −0.0136 (17) | 0.0035 (13) | −0.0123 (16) |
C9 | 0.0482 (18) | 0.066 (2) | 0.0352 (15) | 0.0011 (14) | 0.0032 (12) | −0.0057 (14) |
C10 | 0.0445 (16) | 0.0473 (16) | 0.0247 (13) | 0.0014 (13) | 0.0037 (11) | −0.0009 (11) |
C11 | 0.0418 (16) | 0.0352 (15) | 0.0369 (14) | 0.0096 (11) | 0.0000 (11) | 0.0009 (11) |
C12 | 0.0393 (15) | 0.0360 (14) | 0.0333 (14) | 0.0066 (11) | 0.0064 (11) | 0.0002 (11) |
C13 | 0.0472 (17) | 0.0475 (17) | 0.0331 (15) | 0.0040 (14) | 0.0025 (12) | −0.0012 (13) |
C14 | 0.0384 (16) | 0.0432 (15) | 0.0424 (15) | 0.0003 (12) | 0.0084 (12) | −0.0016 (12) |
C15 | 0.0352 (16) | 0.0543 (18) | 0.0522 (17) | −0.0018 (13) | −0.0001 (13) | 0.0018 (14) |
C16 | 0.0435 (17) | 0.0651 (19) | 0.0406 (16) | −0.0135 (14) | −0.0051 (12) | 0.0041 (14) |
C17 | 0.0517 (18) | 0.0574 (18) | 0.0405 (16) | −0.0093 (14) | 0.0084 (13) | −0.0111 (13) |
C18 | 0.0406 (16) | 0.0454 (15) | 0.0451 (16) | 0.0014 (12) | 0.0082 (12) | −0.0047 (13) |
C19 | 0.0350 (14) | 0.0331 (14) | 0.0354 (14) | −0.0008 (11) | 0.0077 (11) | 0.0003 (11) |
C20 | 0.0385 (15) | 0.0330 (14) | 0.0367 (14) | 0.0056 (11) | 0.0050 (11) | −0.0019 (11) |
C21 | 0.0411 (16) | 0.0328 (14) | 0.0378 (14) | 0.0070 (11) | 0.0039 (11) | −0.0013 (11) |
C22 | 0.0358 (15) | 0.0355 (14) | 0.0439 (16) | 0.0039 (11) | 0.0030 (11) | −0.0107 (12) |
C23 | 0.0424 (17) | 0.0458 (17) | 0.0556 (18) | 0.0050 (12) | 0.0110 (13) | 0.0006 (14) |
C24 | 0.063 (2) | 0.0551 (19) | 0.0621 (19) | −0.0040 (15) | 0.0253 (16) | −0.0019 (15) |
C25 | 0.051 (2) | 0.058 (2) | 0.086 (3) | −0.0054 (16) | 0.0312 (17) | −0.0236 (18) |
C26 | 0.0395 (18) | 0.067 (2) | 0.083 (2) | 0.0123 (14) | 0.0045 (16) | −0.0260 (18) |
C27 | 0.0470 (18) | 0.0579 (18) | 0.0501 (17) | 0.0131 (14) | 0.0016 (13) | −0.0109 (14) |
N1 | 0.0416 (13) | 0.0496 (14) | 0.0422 (13) | −0.0013 (11) | 0.0084 (10) | −0.0006 (10) |
O1 | 0.0509 (12) | 0.0680 (13) | 0.0486 (12) | 0.0213 (10) | 0.0125 (9) | 0.0012 (9) |
O2 | 0.0661 (14) | 0.0384 (11) | 0.0755 (14) | 0.0037 (10) | 0.0095 (10) | 0.0017 (10) |
C1—N1 | 1.453 (3) | C13—O2 | 1.208 (3) |
C1—H1A | 0.9600 | C13—N1 | 1.382 (3) |
C1—H1B | 0.9600 | C14—C15 | 1.378 (3) |
C1—H1C | 0.9600 | C14—C19 | 1.383 (3) |
C2—O1 | 1.210 (3) | C14—H14 | 0.9300 |
C2—N1 | 1.406 (3) | C15—C16 | 1.376 (3) |
C2—C3 | 1.467 (3) | C15—H15 | 0.9300 |
C3—C4 | 1.333 (3) | C16—C17 | 1.378 (3) |
C3—C12 | 1.491 (3) | C16—H16 | 0.9300 |
C4—C5 | 1.453 (3) | C17—C18 | 1.371 (3) |
C4—H4 | 0.9300 | C17—H17 | 0.9300 |
C5—C6 | 1.392 (3) | C18—C19 | 1.399 (3) |
C5—C10 | 1.407 (3) | C18—H18 | 0.9300 |
C6—C7 | 1.372 (4) | C19—C20 | 1.461 (3) |
C6—H6 | 0.9300 | C20—C21 | 1.345 (3) |
C7—C8 | 1.379 (4) | C21—C22 | 1.462 (3) |
C7—H7 | 0.9300 | C22—C27 | 1.381 (3) |
C8—C9 | 1.387 (3) | C22—C23 | 1.388 (3) |
C8—H8 | 0.9300 | C23—C24 | 1.376 (3) |
C9—C10 | 1.376 (3) | C23—H23 | 0.9300 |
C9—H9 | 0.9300 | C24—C25 | 1.365 (4) |
C10—C11 | 1.509 (3) | C24—H24 | 0.9300 |
C11—C21 | 1.525 (3) | C25—C26 | 1.369 (4) |
C11—C12 | 1.560 (3) | C25—H25 | 0.9300 |
C11—H11 | 0.9800 | C26—C27 | 1.378 (4) |
C12—C13 | 1.522 (3) | C26—H26 | 0.9300 |
C12—C20 | 1.541 (3) | C27—H27 | 0.9300 |
N1—C1—H1A | 109.5 | N1—C13—C12 | 107.3 (2) |
N1—C1—H1B | 109.5 | C15—C14—C19 | 121.6 (2) |
H1A—C1—H1B | 109.5 | C15—C14—H14 | 119.2 |
N1—C1—H1C | 109.5 | C19—C14—H14 | 119.2 |
H1A—C1—H1C | 109.5 | C16—C15—C14 | 119.8 (2) |
H1B—C1—H1C | 109.5 | C16—C15—H15 | 120.1 |
O1—C2—N1 | 123.5 (2) | C14—C15—H15 | 120.1 |
O1—C2—C3 | 130.5 (3) | C15—C16—C17 | 119.8 (2) |
N1—C2—C3 | 105.9 (2) | C15—C16—H16 | 120.1 |
C4—C3—C2 | 127.4 (2) | C17—C16—H16 | 120.1 |
C4—C3—C12 | 122.9 (2) | C18—C17—C16 | 120.4 (2) |
C2—C3—C12 | 108.4 (2) | C18—C17—H17 | 119.8 |
C3—C4—C5 | 121.7 (2) | C16—C17—H17 | 119.8 |
C3—C4—H4 | 119.1 | C17—C18—C19 | 120.8 (2) |
C5—C4—H4 | 119.1 | C17—C18—H18 | 119.6 |
C6—C5—C10 | 119.1 (3) | C19—C18—H18 | 119.6 |
C6—C5—C4 | 120.3 (2) | C14—C19—C18 | 117.6 (2) |
C10—C5—C4 | 120.2 (2) | C14—C19—C20 | 121.9 (2) |
C7—C6—C5 | 121.2 (3) | C18—C19—C20 | 120.5 (2) |
C7—C6—H6 | 119.4 | C21—C20—C19 | 136.1 (2) |
C5—C6—H6 | 119.4 | C21—C20—C12 | 93.44 (19) |
C6—C7—C8 | 120.0 (3) | C19—C20—C12 | 130.4 (2) |
C6—C7—H7 | 120.0 | C20—C21—C22 | 135.4 (2) |
C8—C7—H7 | 120.0 | C20—C21—C11 | 94.53 (19) |
C7—C8—C9 | 119.0 (3) | C22—C21—C11 | 129.8 (2) |
C7—C8—H8 | 120.5 | C27—C22—C23 | 118.3 (2) |
C9—C8—H8 | 120.5 | C27—C22—C21 | 121.3 (2) |
C10—C9—C8 | 122.2 (3) | C23—C22—C21 | 120.4 (2) |
C10—C9—H9 | 118.9 | C24—C23—C22 | 120.5 (2) |
C8—C9—H9 | 118.9 | C24—C23—H23 | 119.8 |
C9—C10—C5 | 118.4 (2) | C22—C23—H23 | 119.8 |
C9—C10—C11 | 120.0 (2) | C25—C24—C23 | 120.4 (3) |
C5—C10—C11 | 121.5 (2) | C25—C24—H24 | 119.8 |
C10—C11—C21 | 111.00 (19) | C23—C24—H24 | 119.8 |
C10—C11—C12 | 114.87 (19) | C24—C25—C26 | 119.9 (3) |
C21—C11—C12 | 86.05 (17) | C24—C25—H25 | 120.0 |
C10—C11—H11 | 114.0 | C26—C25—H25 | 120.0 |
C21—C11—H11 | 114.0 | C25—C26—C27 | 120.1 (3) |
C12—C11—H11 | 114.0 | C25—C26—H26 | 120.0 |
C3—C12—C13 | 102.7 (2) | C27—C26—H26 | 120.0 |
C3—C12—C20 | 119.68 (19) | C26—C27—C22 | 120.7 (3) |
C13—C12—C20 | 111.06 (19) | C26—C27—H27 | 119.6 |
C3—C12—C11 | 116.3 (2) | C22—C27—H27 | 119.6 |
C13—C12—C11 | 121.9 (2) | C13—N1—C2 | 113.0 (2) |
C20—C12—C11 | 85.83 (17) | C13—N1—C1 | 123.5 (2) |
O2—C13—N1 | 124.5 (2) | C2—N1—C1 | 123.4 (2) |
O2—C13—C12 | 128.1 (2) | ||
O1—C2—C3—C4 | −23.2 (4) | C16—C17—C18—C19 | −0.6 (4) |
N1—C2—C3—C4 | 155.4 (2) | C15—C14—C19—C18 | 2.4 (3) |
O1—C2—C3—C12 | 170.0 (2) | C15—C14—C19—C20 | −175.7 (2) |
N1—C2—C3—C12 | −11.4 (2) | C17—C18—C19—C14 | −1.3 (3) |
C2—C3—C4—C5 | −160.1 (2) | C17—C18—C19—C20 | 176.8 (2) |
C12—C3—C4—C5 | 4.9 (3) | C14—C19—C20—C21 | 150.3 (3) |
C3—C4—C5—C6 | −176.9 (2) | C18—C19—C20—C21 | −27.7 (4) |
C3—C4—C5—C10 | 9.7 (3) | C14—C19—C20—C12 | −31.9 (4) |
C10—C5—C6—C7 | −0.1 (4) | C18—C19—C20—C12 | 150.1 (2) |
C4—C5—C6—C7 | −173.6 (2) | C3—C12—C20—C21 | −121.1 (2) |
C5—C6—C7—C8 | 1.5 (4) | C13—C12—C20—C21 | 119.6 (2) |
C6—C7—C8—C9 | −1.0 (4) | C11—C12—C20—C21 | −3.11 (19) |
C7—C8—C9—C10 | −0.9 (4) | C3—C12—C20—C19 | 60.5 (3) |
C8—C9—C10—C5 | 2.3 (4) | C13—C12—C20—C19 | −58.9 (3) |
C8—C9—C10—C11 | −174.1 (2) | C11—C12—C20—C19 | 178.5 (2) |
C6—C5—C10—C9 | −1.8 (3) | C19—C20—C21—C22 | −4.2 (5) |
C4—C5—C10—C9 | 171.7 (2) | C12—C20—C21—C22 | 177.5 (3) |
C6—C5—C10—C11 | 174.6 (2) | C19—C20—C21—C11 | −178.5 (3) |
C4—C5—C10—C11 | −11.9 (3) | C12—C20—C21—C11 | 3.18 (19) |
C9—C10—C11—C21 | 81.3 (3) | C10—C11—C21—C20 | 112.0 (2) |
C5—C10—C11—C21 | −95.0 (2) | C12—C11—C21—C20 | −3.14 (19) |
C9—C10—C11—C12 | 176.8 (2) | C10—C11—C21—C22 | −62.8 (3) |
C5—C10—C11—C12 | 0.5 (3) | C12—C11—C21—C22 | −177.9 (2) |
C4—C3—C12—C13 | −151.6 (2) | C20—C21—C22—C27 | 148.6 (3) |
C2—C3—C12—C13 | 16.0 (2) | C11—C21—C22—C27 | −38.8 (4) |
C4—C3—C12—C20 | 84.9 (3) | C20—C21—C22—C23 | −31.2 (4) |
C2—C3—C12—C20 | −107.6 (2) | C11—C21—C22—C23 | 141.4 (2) |
C4—C3—C12—C11 | −15.9 (3) | C27—C22—C23—C24 | −1.9 (4) |
C2—C3—C12—C11 | 151.61 (19) | C21—C22—C23—C24 | 177.9 (2) |
C10—C11—C12—C3 | 12.6 (3) | C22—C23—C24—C25 | 0.6 (4) |
C21—C11—C12—C3 | 123.9 (2) | C23—C24—C25—C26 | 1.3 (4) |
C10—C11—C12—C13 | 139.1 (2) | C24—C25—C26—C27 | −1.8 (4) |
C21—C11—C12—C13 | −109.5 (2) | C25—C26—C27—C22 | 0.4 (4) |
C10—C11—C12—C20 | −108.6 (2) | C23—C22—C27—C26 | 1.4 (4) |
C21—C11—C12—C20 | 2.74 (16) | C21—C22—C27—C26 | −178.4 (2) |
C3—C12—C13—O2 | 168.5 (2) | O2—C13—N1—C2 | −174.5 (2) |
C20—C12—C13—O2 | −62.4 (3) | C12—C13—N1—C2 | 8.8 (3) |
C11—C12—C13—O2 | 36.1 (4) | O2—C13—N1—C1 | 3.0 (4) |
C3—C12—C13—N1 | −15.0 (2) | C12—C13—N1—C1 | −173.8 (2) |
C20—C12—C13—N1 | 114.1 (2) | O1—C2—N1—C13 | −179.9 (2) |
C11—C12—C13—N1 | −147.4 (2) | C3—C2—N1—C13 | 1.5 (3) |
C19—C14—C15—C16 | −1.6 (4) | O1—C2—N1—C1 | 2.7 (4) |
C14—C15—C16—C17 | −0.3 (4) | C3—C2—N1—C1 | −175.9 (2) |
C15—C16—C17—C18 | 1.4 (4) |
Experimental details
Crystal data | |
Chemical formula | C27H19NO2 |
Mr | 389.43 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.763 (2), 7.9925 (15), 23.438 (5) |
β (°) | 97.326 (3) |
V (Å3) | 1999.8 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.28 × 0.22 × 0.08 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10516, 3715, 2456 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.123, 1.01 |
No. of reflections | 3715 |
No. of parameters | 272 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL.
In the studies of photochemistry of naphthalenedicarboximides with alkynes, it has been found that the photoinduced cycloadditions of N-methyl-1,8-naphthalenedicarboximides (NI18) with alkynes followed the pathway of NI18 with alkenes (Liu et al., 2006), but that is not the case for N-methylnaphthalene-2,3-dicarboximide (NI23). UV irradiation of NI23 in the presence of diphenylacetylene in benzene solution resulted in the novel adduct (I) and its structure is reported here (Figure 1).
The bond lengths and angles in (I) show normal values except for the geometry of the cyclobutene ring (Table 1). The C20—C21 bond length of 1.345 (3)Å is nearly the same as that in 4-methyl-1,2-diphenylbenzo[de]cyclobut[i]isoquinoline- 3,5(2H)-dione(1.346 (3) Å) (Liu et al., 2006), but is longer than those of 4,5,9,10-tetrahydro-4- methyl-2-phenyl-9,10-epoxy-3H,10aH-cyclobuta[benzo[2,3,4-de]- isoquinoline-3,5-dione (1.324 (2) Å) (Liu et al., 2003), Such elongation is considered to be caused by the steric effect of the bulky phenyl substituents on C20 and C21, respectively. The cyclobutene ring in the molecule is almost perpendicular to the plane of dihydronaphthalimide, the interplanar angle between the cyclobutene ring and the plane through the two six membered rings of the naphthalimide is 70.66 (9). The interplanar angle between the two benzene substituents on the cyclobutene ring is 42.47 (8).