1,4-Dimethyl-2-phenyl-3H,10aH-4-azacyclobuta[c]phenylene-3,5-dione

The title compound, C₂₂H₁₇NO₂, was obtained by the photoreaction of N-methyl-1,8-naphthalene­dicarboximide with 1-phenyl­propyne. The planar cyclo­butene ring makes a dihedral angle of 71.7 (2)° with the benzene ring of the 1,2-dihydro­naphthalene group. There are intra­molecular C—H...O hydrogen bonds, and inter­molecular C—H...O inter­actions help to stabilize the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.059
• wR factor = 0.193
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1,4-dimethyl-2-phenyl-3H,10aH-benzo[de]cyclobut[I] isoquinoline-3,5-dione

Crystal data

C22H17NO2	F(000) = 688
Mr = 327.37	Dx = 1.281 Mg m^−3
Monoclinic, P21/c	Melting point: 164 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.327 (2) Å	Cell parameters from 25 reflections
b = 9.2270 (18) Å	θ = 10–13°
c = 16.397 (3) Å	µ = 0.08 mm^−1
β = 97.95 (3)°	T = 298 K
V = 1697.2 (6) Å^3	Block, yellow
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	1792 reflections with I > 2σ(I)
Radiation source: fine-focus sealedtube	Rint = 0.048
Graphite monochromator	θmax = 26.0°, θmin = 1.8°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (XCAD4; Harms & Wocadlo, 1995)	k = 0→10
Tmin = 0.963, Tmax = 0.984	l = −19→19
3445 measured reflections	3 standard reflections every 200 reflections
3278 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.193	w = 1/[σ^2(Fo^2) + (0.1017P)^2] whereP = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
3278 reflections	Δρmax = 0.21 e Å^−3
227 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N	0.2215 (2)	0.8061 (2)	1.02219 (15)	0.0581 (6)
O1	0.1493 (2)	1.0124 (2)	0.96198 (17)	0.0993 (9)
O2	0.28457 (17)	0.5972 (2)	1.08526 (12)	0.0647 (6)
C1	0.2963 (3)	0.8890 (4)	1.0855 (2)	0.0881 (11)
H1A	0.2831	0.9907	1.0760	0.132*
H1B	0.3787	0.8668	1.0834	0.132*
H1C	0.2764	0.8639	1.1388	0.132*
C2	0.1466 (3)	0.8820 (3)	0.9635 (2)	0.0629 (8)
C3	0.0614 (2)	0.7975 (3)	0.90551 (17)	0.0520 (7)
C4	−0.0311 (3)	0.8688 (3)	0.85623 (19)	0.0645 (8)
H4A	−0.0371	0.9692	0.8581	0.077*
C5	−0.1136 (3)	0.7899 (4)	0.80483 (19)	0.0674 (9)
H5A	−0.1734	0.8372	0.7703	0.081*
C6	−0.1073 (2)	0.6406 (4)	0.80469 (17)	0.0627 (8)
H6A	−0.1650	0.5887	0.7709	0.075*
C7	−0.0169 (2)	0.5646 (3)	0.85369 (16)	0.0509 (7)
C8	0.0710 (2)	0.6467 (3)	0.90255 (15)	0.0437 (6)
C9	0.1760 (2)	0.5736 (3)	0.95020 (15)	0.0438 (6)
C10	0.2287 (2)	0.6559 (3)	1.02608 (17)	0.0493 (7)
C11	−0.0158 (3)	0.4083 (3)	0.86083 (18)	0.0603 (8)
H11A	−0.0735	0.3558	0.8273	0.072*
C12	0.0629 (2)	0.3364 (3)	0.91246 (18)	0.0600 (8)
H12A	0.0519	0.2373	0.9183	0.072*
C13	0.1682 (2)	0.4049 (3)	0.96181 (16)	0.0502 (7)
H13A	0.1808	0.3741	1.0196	0.060*
C14	0.2800 (2)	0.3956 (3)	0.91982 (16)	0.0504 (7)
C15	0.3523 (3)	0.2672 (3)	0.9038 (2)	0.0699 (9)
H15A	0.4168	0.2970	0.8754	0.105*
H15B	0.3030	0.1989	0.8706	0.105*
H15C	0.3837	0.2227	0.9552	0.105*
C16	0.2837 (2)	0.5371 (3)	0.90320 (15)	0.0450 (6)
C17	0.3634 (2)	0.6359 (3)	0.86563 (15)	0.0450 (6)
C18	0.4863 (2)	0.6169 (3)	0.88189 (19)	0.0620 (8)
H18A	0.5174	0.5407	0.9153	0.074*
C19	0.5620 (3)	0.7098 (4)	0.8490 (2)	0.0723 (9)
H19A	0.6437	0.6934	0.8590	0.087*
C20	0.5193 (3)	0.8259 (4)	0.80196 (18)	0.0667 (8)
H20A	0.5715	0.8902	0.7818	0.080*
C21	0.3975 (3)	0.8461 (4)	0.7847 (2)	0.0736 (9)
H21A	0.3672	0.9227	0.7514	0.088*
C22	0.3212 (3)	0.7528 (3)	0.81711 (18)	0.0664 (9)
H22A	0.2394	0.7685	0.8061	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N	0.0479 (13)	0.0512 (14)	0.0735 (16)	0.0020 (11)	0.0028 (12)	−0.0070 (12)
O1	0.0992 (19)	0.0441 (14)	0.146 (2)	0.0014 (12)	−0.0129 (17)	0.0039 (14)
O2	0.0580 (12)	0.0703 (14)	0.0624 (12)	0.0120 (10)	−0.0038 (10)	0.0002 (11)
C1	0.075 (2)	0.073 (2)	0.108 (3)	0.0020 (18)	−0.018 (2)	−0.024 (2)
C2	0.0556 (18)	0.0447 (18)	0.089 (2)	0.0068 (14)	0.0135 (16)	0.0055 (16)
C3	0.0409 (15)	0.0532 (17)	0.0632 (17)	0.0067 (12)	0.0120 (13)	0.0115 (13)
C4	0.0542 (18)	0.0616 (19)	0.078 (2)	0.0127 (15)	0.0118 (16)	0.0181 (16)
C5	0.0458 (17)	0.085 (2)	0.070 (2)	0.0116 (16)	0.0031 (15)	0.0207 (17)
C6	0.0419 (16)	0.088 (2)	0.0564 (17)	−0.0012 (15)	0.0012 (13)	0.0065 (16)
C7	0.0388 (14)	0.0616 (19)	0.0537 (16)	0.0020 (12)	0.0113 (12)	0.0037 (13)
C8	0.0362 (13)	0.0462 (15)	0.0501 (15)	0.0032 (11)	0.0106 (11)	0.0038 (12)
C9	0.0353 (13)	0.0445 (15)	0.0526 (15)	0.0026 (11)	0.0092 (11)	0.0011 (12)
C10	0.0378 (14)	0.0552 (17)	0.0554 (16)	0.0074 (13)	0.0078 (12)	0.0025 (14)
C11	0.0469 (17)	0.067 (2)	0.0674 (19)	−0.0101 (14)	0.0110 (14)	−0.0106 (15)
C12	0.0549 (18)	0.0534 (18)	0.075 (2)	−0.0045 (14)	0.0207 (15)	−0.0007 (15)
C13	0.0520 (16)	0.0472 (15)	0.0523 (15)	0.0053 (12)	0.0109 (13)	0.0059 (12)
C14	0.0452 (15)	0.0501 (17)	0.0564 (16)	0.0079 (12)	0.0090 (12)	0.0011 (13)
C15	0.066 (2)	0.0579 (19)	0.089 (2)	0.0161 (15)	0.0212 (17)	0.0030 (16)
C16	0.0368 (13)	0.0490 (16)	0.0490 (15)	0.0062 (11)	0.0058 (11)	−0.0001 (12)
C17	0.0390 (13)	0.0531 (16)	0.0435 (14)	0.0064 (12)	0.0082 (11)	0.0028 (12)
C18	0.0409 (15)	0.073 (2)	0.0727 (19)	0.0086 (14)	0.0086 (14)	0.0179 (16)
C19	0.0385 (16)	0.093 (3)	0.085 (2)	−0.0030 (16)	0.0079 (15)	0.0108 (19)
C20	0.0572 (18)	0.080 (2)	0.0651 (19)	−0.0144 (17)	0.0157 (15)	0.0068 (17)
C21	0.067 (2)	0.079 (2)	0.076 (2)	0.0060 (17)	0.0138 (17)	0.0307 (18)
C22	0.0405 (15)	0.085 (2)	0.075 (2)	0.0066 (15)	0.0096 (14)	0.0263 (17)

Geometric parameters (Å, º)

N—C2	1.382 (4)	C11—C12	1.320 (4)
N—C10	1.389 (4)	C11—H11A	0.9300
N—C1	1.463 (4)	C12—C13	1.487 (4)
O1—C2	1.204 (3)	C12—H12A	0.9300
O2—C10	1.211 (3)	C13—C14	1.525 (4)
C1—H1A	0.9600	C13—H13A	0.9800
C1—H1B	0.9600	C14—C16	1.335 (4)
C1—H1C	0.9600	C14—C15	1.484 (4)
C2—C3	1.479 (4)	C15—H15A	0.9600
C3—C4	1.397 (4)	C15—H15B	0.9600
C3—C8	1.397 (4)	C15—H15C	0.9600
C4—C5	1.376 (4)	C16—C17	1.476 (3)
C4—H4A	0.9300	C17—C22	1.385 (4)
C5—C6	1.380 (4)	C17—C18	1.392 (3)
C5—H5A	0.9300	C18—C19	1.374 (4)
C6—C7	1.399 (4)	C18—H18A	0.9300
C6—H6A	0.9300	C19—C20	1.369 (4)
C7—C8	1.410 (4)	C19—H19A	0.9300
C7—C11	1.446 (4)	C20—C21	1.382 (4)
C8—C9	1.491 (3)	C20—H20A	0.9300
C9—C10	1.509 (4)	C21—C22	1.378 (4)
C9—C16	1.567 (3)	C21—H21A	0.9300
C9—C13	1.572 (3)	C22—H22A	0.9300
C2—N—C10	124.3 (2)	C7—C11—H11A	118.3
C2—N—C1	118.0 (2)	C11—C12—C13	123.7 (3)
C10—N—C1	117.7 (2)	C11—C12—H12A	118.1
N—C1—H1A	109.5	C13—C12—H12A	118.1
N—C1—H1B	109.5	C12—C13—C14	112.6 (2)
H1A—C1—H1B	109.5	C12—C13—C9	114.2 (2)
N—C1—H1C	109.5	C14—C13—C9	86.39 (19)
H1A—C1—H1C	109.5	C12—C13—H13A	113.6
H1B—C1—H1C	109.5	C14—C13—H13A	113.6
O1—C2—N	120.4 (3)	C9—C13—H13A	113.6
O1—C2—C3	122.0 (3)	C16—C14—C15	135.3 (3)
N—C2—C3	117.6 (2)	C16—C14—C13	95.1 (2)
C4—C3—C8	120.3 (3)	C15—C14—C13	129.6 (2)
C4—C3—C2	119.6 (3)	C14—C15—H15A	109.5
C8—C3—C2	120.0 (2)	C14—C15—H15B	109.5
C5—C4—C3	119.8 (3)	H15A—C15—H15B	109.5
C5—C4—H4A	120.1	C14—C15—H15C	109.5
C3—C4—H4A	120.1	H15A—C15—H15C	109.5
C4—C5—C6	119.9 (3)	H15B—C15—H15C	109.5
C4—C5—H5A	120.1	C14—C16—C17	136.6 (2)
C6—C5—H5A	120.1	C14—C16—C9	93.5 (2)
C5—C6—C7	122.3 (3)	C17—C16—C9	129.4 (2)
C5—C6—H6A	118.9	C22—C17—C18	117.7 (3)
C7—C6—H6A	118.9	C22—C17—C16	122.5 (2)
C6—C7—C8	117.4 (3)	C18—C17—C16	119.7 (2)
C6—C7—C11	122.9 (3)	C19—C18—C17	120.6 (3)
C8—C7—C11	119.5 (3)	C19—C18—H18A	119.7
C3—C8—C7	120.2 (2)	C17—C18—H18A	119.7
C3—C8—C9	119.5 (2)	C20—C19—C18	121.2 (3)
C7—C8—C9	120.2 (2)	C20—C19—H19A	119.4
C8—C9—C10	113.6 (2)	C18—C19—H19A	119.4
C8—C9—C16	117.3 (2)	C19—C20—C21	119.1 (3)
C10—C9—C16	105.53 (19)	C19—C20—H20A	120.5
C8—C9—C13	117.2 (2)	C21—C20—H20A	120.5
C10—C9—C13	114.9 (2)	C22—C21—C20	119.9 (3)
C16—C9—C13	84.69 (18)	C22—C21—H21A	120.0
O2—C10—N	120.3 (3)	C20—C21—H21A	120.0
O2—C10—C9	122.6 (2)	C21—C22—C17	121.5 (3)
N—C10—C9	116.8 (2)	C21—C22—H22A	119.2
C12—C11—C7	123.4 (3)	C17—C22—H22A	119.2
C12—C11—H11A	118.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.96	2.25	2.690 (4)	107
C12—H12A···O1^i	0.93	2.41	3.215 (3)	145
C18—H18A···O2^ii	0.93	2.58	3.247 (3)	129

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z+2.