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The title compound, C27H19NO2, is the product of a photochemical reaction between N-methyl­naphthalene-2,3-dicarboximide and diphenyl­acetyl­ene. The cyclo­butene ring in the mol­ecule is almost perpendicular to the plane of the dihydro­naphthalimide system; the inter­planar angle between the cyclo­butene ring and the plane through the two six-membered rings of the naphthalimide system is 70.66 (9)°. The inter­planar angle between the two phenyl substituents on the cyclo­butene ring is 42.47 (8)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807022568/sj2314sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807022568/sj2314Isup2.hkl
Contains datablock I

CCDC reference: 600353

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](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

Comment top

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).

Related literature top

For information on the photochemistry of naphthalenedicarboximides with alkynes see Liu et al. (2006) and for related structures see Liu et al. (2003, 2006).

Experimental top

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).

Refinement top

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.

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. The structure of (I) with the atom-numbering scheme and ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. The formation of (I).
N-Methyl-1,2-diphenylcyclobuteno[3,4-a]naphthalene-2,3-dicarboximide top
Crystal data top
C27H19NO2F(000) = 816
Mr = 389.43Dx = 1.293 Mg m3
Monoclinic, P21/cMelting point: 505 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 10.763 (2) ÅCell parameters from 1602 reflections
b = 7.9925 (15) Åθ = 2.4–20.9°
c = 23.438 (5) ŵ = 0.08 mm1
β = 97.326 (3)°T = 298 K
V = 1999.8 (7) Å3Plate, colourless
Z = 40.28 × 0.22 × 0.08 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2456 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.062
Graphite monochromatorθmax = 25.5°, θmin = 1.9°
φ and ω scansh = 1113
10516 measured reflectionsk = 97
3715 independent reflectionsl = 2824
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)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-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 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C27H19NO2V = 1999.8 (7) Å3
Mr = 389.43Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.763 (2) ŵ = 0.08 mm1
b = 7.9925 (15) ÅT = 298 K
c = 23.438 (5) Å0.28 × 0.22 × 0.08 mm
β = 97.326 (3)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2456 reflections with I > 2σ(I)
10516 measured reflectionsRint = 0.062
3715 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0580 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å3
3715 reflectionsΔρmin = 0.15 e Å3
272 parameters
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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5270 (3)0.7812 (4)0.55850 (12)0.0659 (9)
H1A0.52370.78750.51740.099*
H1B0.60280.72570.57430.099*
H1C0.52560.89210.57410.099*
C20.4147 (2)0.5119 (3)0.57395 (9)0.0415 (6)
C30.2884 (2)0.4690 (3)0.58640 (9)0.0362 (6)
C40.2254 (2)0.3278 (3)0.57293 (9)0.0417 (6)
H40.26920.23240.56470.050*
C50.0900 (2)0.3192 (3)0.57082 (9)0.0406 (6)
C60.0276 (3)0.1680 (3)0.55931 (10)0.0528 (7)
H60.07380.07050.55680.063*
C70.1008 (3)0.1601 (4)0.55158 (11)0.0608 (8)
H70.14080.05760.54480.073*
C80.1705 (3)0.3042 (4)0.55384 (11)0.0577 (8)
H80.25760.30000.54800.069*
C90.1089 (2)0.4554 (4)0.56487 (10)0.0501 (7)
H90.15600.55260.56580.060*
C100.0197 (2)0.4662 (3)0.57446 (9)0.0389 (6)
C110.0817 (2)0.6310 (3)0.59191 (10)0.0384 (6)
H110.04990.72550.56770.046*
C120.2275 (2)0.6241 (3)0.60469 (9)0.0361 (6)
C130.3101 (2)0.7618 (3)0.58514 (10)0.0428 (6)
C140.4107 (2)0.5646 (3)0.72463 (10)0.0410 (6)
H140.43040.50420.69310.049*
C150.4926 (2)0.5629 (3)0.77487 (11)0.0477 (7)
H150.56560.49970.77730.057*
C160.4659 (2)0.6550 (3)0.82139 (11)0.0506 (7)
H160.52060.65380.85550.061*
C170.3578 (2)0.7489 (3)0.81730 (11)0.0496 (7)
H170.34060.81310.84840.060*
C180.2754 (2)0.7483 (3)0.76758 (10)0.0435 (6)
H180.20230.81140.76550.052*
C190.2998 (2)0.6539 (3)0.71998 (9)0.0342 (6)
C200.2084 (2)0.6472 (3)0.66827 (10)0.0360 (6)
C210.0834 (2)0.6619 (3)0.65621 (10)0.0373 (6)
C220.0208 (2)0.6824 (3)0.69000 (10)0.0386 (6)
C230.0146 (2)0.6137 (3)0.74466 (11)0.0475 (7)
H230.05510.55120.75940.057*
C240.1108 (3)0.6373 (3)0.77724 (12)0.0585 (8)
H240.10540.59160.81400.070*
C250.2141 (3)0.7276 (4)0.75599 (15)0.0628 (9)
H250.27810.74510.77850.075*
C260.2234 (3)0.7922 (4)0.70151 (15)0.0635 (9)
H260.29480.85100.68660.076*
C270.1271 (2)0.7703 (3)0.66871 (12)0.0521 (7)
H270.13380.81520.63180.062*
N10.41972 (19)0.6876 (3)0.57308 (8)0.0442 (5)
O10.50087 (17)0.4229 (2)0.56464 (7)0.0553 (5)
O20.28991 (17)0.9106 (2)0.58275 (8)0.0599 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.056 (2)0.076 (2)0.068 (2)0.0136 (16)0.0180 (15)0.0095 (16)
C20.0456 (17)0.0540 (18)0.0244 (13)0.0114 (13)0.0026 (11)0.0012 (12)
C30.0397 (15)0.0406 (15)0.0282 (13)0.0099 (12)0.0038 (11)0.0018 (11)
C40.0517 (18)0.0376 (15)0.0352 (14)0.0127 (13)0.0033 (12)0.0013 (12)
C50.0518 (17)0.0427 (16)0.0270 (13)0.0008 (13)0.0044 (11)0.0015 (12)
C60.066 (2)0.0465 (17)0.0441 (17)0.0019 (15)0.0011 (14)0.0001 (13)
C70.074 (2)0.062 (2)0.0461 (17)0.0197 (17)0.0068 (15)0.0055 (15)
C80.0507 (18)0.082 (2)0.0396 (16)0.0136 (17)0.0035 (13)0.0123 (16)
C90.0482 (18)0.066 (2)0.0352 (15)0.0011 (14)0.0032 (12)0.0057 (14)
C100.0445 (16)0.0473 (16)0.0247 (13)0.0014 (13)0.0037 (11)0.0009 (11)
C110.0418 (16)0.0352 (15)0.0369 (14)0.0096 (11)0.0000 (11)0.0009 (11)
C120.0393 (15)0.0360 (14)0.0333 (14)0.0066 (11)0.0064 (11)0.0002 (11)
C130.0472 (17)0.0475 (17)0.0331 (15)0.0040 (14)0.0025 (12)0.0012 (13)
C140.0384 (16)0.0432 (15)0.0424 (15)0.0003 (12)0.0084 (12)0.0016 (12)
C150.0352 (16)0.0543 (18)0.0522 (17)0.0018 (13)0.0001 (13)0.0018 (14)
C160.0435 (17)0.0651 (19)0.0406 (16)0.0135 (14)0.0051 (12)0.0041 (14)
C170.0517 (18)0.0574 (18)0.0405 (16)0.0093 (14)0.0084 (13)0.0111 (13)
C180.0406 (16)0.0454 (15)0.0451 (16)0.0014 (12)0.0082 (12)0.0047 (13)
C190.0350 (14)0.0331 (14)0.0354 (14)0.0008 (11)0.0077 (11)0.0003 (11)
C200.0385 (15)0.0330 (14)0.0367 (14)0.0056 (11)0.0050 (11)0.0019 (11)
C210.0411 (16)0.0328 (14)0.0378 (14)0.0070 (11)0.0039 (11)0.0013 (11)
C220.0358 (15)0.0355 (14)0.0439 (16)0.0039 (11)0.0030 (11)0.0107 (12)
C230.0424 (17)0.0458 (17)0.0556 (18)0.0050 (12)0.0110 (13)0.0006 (14)
C240.063 (2)0.0551 (19)0.0621 (19)0.0040 (15)0.0253 (16)0.0019 (15)
C250.051 (2)0.058 (2)0.086 (3)0.0054 (16)0.0312 (17)0.0236 (18)
C260.0395 (18)0.067 (2)0.083 (2)0.0123 (14)0.0045 (16)0.0260 (18)
C270.0470 (18)0.0579 (18)0.0501 (17)0.0131 (14)0.0016 (13)0.0109 (14)
N10.0416 (13)0.0496 (14)0.0422 (13)0.0013 (11)0.0084 (10)0.0006 (10)
O10.0509 (12)0.0680 (13)0.0486 (12)0.0213 (10)0.0125 (9)0.0012 (9)
O20.0661 (14)0.0384 (11)0.0755 (14)0.0037 (10)0.0095 (10)0.0017 (10)
Geometric parameters (Å, º) top
C1—N11.453 (3)C13—O21.208 (3)
C1—H1A0.9600C13—N11.382 (3)
C1—H1B0.9600C14—C151.378 (3)
C1—H1C0.9600C14—C191.383 (3)
C2—O11.210 (3)C14—H140.9300
C2—N11.406 (3)C15—C161.376 (3)
C2—C31.467 (3)C15—H150.9300
C3—C41.333 (3)C16—C171.378 (3)
C3—C121.491 (3)C16—H160.9300
C4—C51.453 (3)C17—C181.371 (3)
C4—H40.9300C17—H170.9300
C5—C61.392 (3)C18—C191.399 (3)
C5—C101.407 (3)C18—H180.9300
C6—C71.372 (4)C19—C201.461 (3)
C6—H60.9300C20—C211.345 (3)
C7—C81.379 (4)C21—C221.462 (3)
C7—H70.9300C22—C271.381 (3)
C8—C91.387 (3)C22—C231.388 (3)
C8—H80.9300C23—C241.376 (3)
C9—C101.376 (3)C23—H230.9300
C9—H90.9300C24—C251.365 (4)
C10—C111.509 (3)C24—H240.9300
C11—C211.525 (3)C25—C261.369 (4)
C11—C121.560 (3)C25—H250.9300
C11—H110.9800C26—C271.378 (4)
C12—C131.522 (3)C26—H260.9300
C12—C201.541 (3)C27—H270.9300
N1—C1—H1A109.5N1—C13—C12107.3 (2)
N1—C1—H1B109.5C15—C14—C19121.6 (2)
H1A—C1—H1B109.5C15—C14—H14119.2
N1—C1—H1C109.5C19—C14—H14119.2
H1A—C1—H1C109.5C16—C15—C14119.8 (2)
H1B—C1—H1C109.5C16—C15—H15120.1
O1—C2—N1123.5 (2)C14—C15—H15120.1
O1—C2—C3130.5 (3)C15—C16—C17119.8 (2)
N1—C2—C3105.9 (2)C15—C16—H16120.1
C4—C3—C2127.4 (2)C17—C16—H16120.1
C4—C3—C12122.9 (2)C18—C17—C16120.4 (2)
C2—C3—C12108.4 (2)C18—C17—H17119.8
C3—C4—C5121.7 (2)C16—C17—H17119.8
C3—C4—H4119.1C17—C18—C19120.8 (2)
C5—C4—H4119.1C17—C18—H18119.6
C6—C5—C10119.1 (3)C19—C18—H18119.6
C6—C5—C4120.3 (2)C14—C19—C18117.6 (2)
C10—C5—C4120.2 (2)C14—C19—C20121.9 (2)
C7—C6—C5121.2 (3)C18—C19—C20120.5 (2)
C7—C6—H6119.4C21—C20—C19136.1 (2)
C5—C6—H6119.4C21—C20—C1293.44 (19)
C6—C7—C8120.0 (3)C19—C20—C12130.4 (2)
C6—C7—H7120.0C20—C21—C22135.4 (2)
C8—C7—H7120.0C20—C21—C1194.53 (19)
C7—C8—C9119.0 (3)C22—C21—C11129.8 (2)
C7—C8—H8120.5C27—C22—C23118.3 (2)
C9—C8—H8120.5C27—C22—C21121.3 (2)
C10—C9—C8122.2 (3)C23—C22—C21120.4 (2)
C10—C9—H9118.9C24—C23—C22120.5 (2)
C8—C9—H9118.9C24—C23—H23119.8
C9—C10—C5118.4 (2)C22—C23—H23119.8
C9—C10—C11120.0 (2)C25—C24—C23120.4 (3)
C5—C10—C11121.5 (2)C25—C24—H24119.8
C10—C11—C21111.00 (19)C23—C24—H24119.8
C10—C11—C12114.87 (19)C24—C25—C26119.9 (3)
C21—C11—C1286.05 (17)C24—C25—H25120.0
C10—C11—H11114.0C26—C25—H25120.0
C21—C11—H11114.0C25—C26—C27120.1 (3)
C12—C11—H11114.0C25—C26—H26120.0
C3—C12—C13102.7 (2)C27—C26—H26120.0
C3—C12—C20119.68 (19)C26—C27—C22120.7 (3)
C13—C12—C20111.06 (19)C26—C27—H27119.6
C3—C12—C11116.3 (2)C22—C27—H27119.6
C13—C12—C11121.9 (2)C13—N1—C2113.0 (2)
C20—C12—C1185.83 (17)C13—N1—C1123.5 (2)
O2—C13—N1124.5 (2)C2—N1—C1123.4 (2)
O2—C13—C12128.1 (2)
O1—C2—C3—C423.2 (4)C16—C17—C18—C190.6 (4)
N1—C2—C3—C4155.4 (2)C15—C14—C19—C182.4 (3)
O1—C2—C3—C12170.0 (2)C15—C14—C19—C20175.7 (2)
N1—C2—C3—C1211.4 (2)C17—C18—C19—C141.3 (3)
C2—C3—C4—C5160.1 (2)C17—C18—C19—C20176.8 (2)
C12—C3—C4—C54.9 (3)C14—C19—C20—C21150.3 (3)
C3—C4—C5—C6176.9 (2)C18—C19—C20—C2127.7 (4)
C3—C4—C5—C109.7 (3)C14—C19—C20—C1231.9 (4)
C10—C5—C6—C70.1 (4)C18—C19—C20—C12150.1 (2)
C4—C5—C6—C7173.6 (2)C3—C12—C20—C21121.1 (2)
C5—C6—C7—C81.5 (4)C13—C12—C20—C21119.6 (2)
C6—C7—C8—C91.0 (4)C11—C12—C20—C213.11 (19)
C7—C8—C9—C100.9 (4)C3—C12—C20—C1960.5 (3)
C8—C9—C10—C52.3 (4)C13—C12—C20—C1958.9 (3)
C8—C9—C10—C11174.1 (2)C11—C12—C20—C19178.5 (2)
C6—C5—C10—C91.8 (3)C19—C20—C21—C224.2 (5)
C4—C5—C10—C9171.7 (2)C12—C20—C21—C22177.5 (3)
C6—C5—C10—C11174.6 (2)C19—C20—C21—C11178.5 (3)
C4—C5—C10—C1111.9 (3)C12—C20—C21—C113.18 (19)
C9—C10—C11—C2181.3 (3)C10—C11—C21—C20112.0 (2)
C5—C10—C11—C2195.0 (2)C12—C11—C21—C203.14 (19)
C9—C10—C11—C12176.8 (2)C10—C11—C21—C2262.8 (3)
C5—C10—C11—C120.5 (3)C12—C11—C21—C22177.9 (2)
C4—C3—C12—C13151.6 (2)C20—C21—C22—C27148.6 (3)
C2—C3—C12—C1316.0 (2)C11—C21—C22—C2738.8 (4)
C4—C3—C12—C2084.9 (3)C20—C21—C22—C2331.2 (4)
C2—C3—C12—C20107.6 (2)C11—C21—C22—C23141.4 (2)
C4—C3—C12—C1115.9 (3)C27—C22—C23—C241.9 (4)
C2—C3—C12—C11151.61 (19)C21—C22—C23—C24177.9 (2)
C10—C11—C12—C312.6 (3)C22—C23—C24—C250.6 (4)
C21—C11—C12—C3123.9 (2)C23—C24—C25—C261.3 (4)
C10—C11—C12—C13139.1 (2)C24—C25—C26—C271.8 (4)
C21—C11—C12—C13109.5 (2)C25—C26—C27—C220.4 (4)
C10—C11—C12—C20108.6 (2)C23—C22—C27—C261.4 (4)
C21—C11—C12—C202.74 (16)C21—C22—C27—C26178.4 (2)
C3—C12—C13—O2168.5 (2)O2—C13—N1—C2174.5 (2)
C20—C12—C13—O262.4 (3)C12—C13—N1—C28.8 (3)
C11—C12—C13—O236.1 (4)O2—C13—N1—C13.0 (4)
C3—C12—C13—N115.0 (2)C12—C13—N1—C1173.8 (2)
C20—C12—C13—N1114.1 (2)O1—C2—N1—C13179.9 (2)
C11—C12—C13—N1147.4 (2)C3—C2—N1—C131.5 (3)
C19—C14—C15—C161.6 (4)O1—C2—N1—C12.7 (4)
C14—C15—C16—C170.3 (4)C3—C2—N1—C1175.9 (2)
C15—C16—C17—C181.4 (4)

Experimental details

Crystal data
Chemical formulaC27H19NO2
Mr389.43
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)10.763 (2), 7.9925 (15), 23.438 (5)
β (°) 97.326 (3)
V3)1999.8 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.28 × 0.22 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
10516, 3715, 2456
Rint0.062
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.123, 1.01
No. of reflections3715
No. of parameters272
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.15

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL.

 

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