10-Hydr-oxy-2-aza-penta-cyclo-[10.8.0.0.0.0]icosa-1(12),4(9),5,7,13,15(20),16,18-octa-ene-3,11-dione.

In the title compound, C(19)H(11)NO(3), the isoindolinone ring system is approximately planar with a maximum atomic deviation of 0.071 (1) Å and the five-membered ring of the dihydro-benzo[g]indol-3-one unit assumes an envelope conformation. The naphthalene ring system makes a dihedral angle of 39.47 (4)° with the mean plane of the isoindolinone system. Inter-molecular O-H⋯O and C-H⋯O hydrogen bonding helps to stabilize the crystal structure.

Related literature

For applications of naphthyl­amines, see Valenti et al. (2006 ▶); Black et al. (1994 ▶).

Experimental

Crystal data

C19H11NO3

M = 301.29

Triclinic,

a = 7.3250 (11) Å

b = 9.7916 (16) Å

c = 10.4532 (17) Å

α = 70.401 (13)°

β = 82.503 (13)°

γ = 75.862 (12)°

V = 683.94 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.40 × 0.30 × 0.29 mm

Data collection

Stoe IPDS II diffractometer

7737 measured reflections

3627 independent reflections

3161 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.13

3627 reflections

212 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: X-RED32 (Stoe & Cie, 2005 ▶); cell refinement: X-AREA (Stoe & Cie, 2005 ▶); data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005356/xu5159sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005356/xu5159Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H11NO3	Z = 2
Mr = 301.29	F(000) = 312
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3250 (11) Å	Cell parameters from 1011 reflections
b = 9.7916 (16) Å	θ = 2.3–25.0°
c = 10.4532 (17) Å	µ = 0.10 mm−1
α = 70.401 (13)°	T = 298 K
β = 82.503 (13)°	Block, colorless
γ = 75.862 (12)°	0.40 × 0.30 × 0.29 mm
V = 683.94 (19) Å3

Stoe IPDS II diffractometer	3161 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
graphite	θmax = 29.3°, θmin = 2.3°
rotation method scans	h = −10→10
7737 measured reflections	k = −13→13
3627 independent reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.072P)2 + 0.1037P] where P = (Fo2 + 2Fc2)/3
3627 reflections	(Δ/σ)max < 0.001
212 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.60706 (15)	0.62937 (12)	0.49240 (11)	0.0298 (2)
C2	0.69780 (16)	0.61664 (13)	0.36032 (12)	0.0324 (2)
C3	0.87442 (18)	0.53663 (16)	0.33404 (14)	0.0410 (3)
H3	0.9488	0.4711	0.4042	0.049*
C4	0.9358 (2)	0.55825 (19)	0.19890 (16)	0.0494 (3)
H4	1.0540	0.5065	0.1779	0.059*
C5	0.8237 (2)	0.65604 (19)	0.09393 (15)	0.0502 (3)
H5	0.8694	0.6697	0.0042	0.060*
C6	0.6452 (2)	0.73333 (16)	0.12066 (13)	0.0425 (3)
H6	0.5690	0.7968	0.0507	0.051*
C7	0.58481 (16)	0.71222 (13)	0.25611 (12)	0.0332 (2)
C8	0.40104 (16)	0.77784 (12)	0.31604 (11)	0.0318 (2)
C9	0.33814 (17)	0.94765 (13)	0.28511 (13)	0.0374 (3)
C10	0.29102 (17)	0.97079 (13)	0.41761 (13)	0.0358 (3)
C11	0.19816 (19)	1.10289 (14)	0.44465 (16)	0.0441 (3)
H11	0.1640	1.1909	0.3742	0.053*
C12	0.15988 (19)	1.09807 (16)	0.57670 (17)	0.0469 (3)
H12	0.0981	1.1843	0.5963	0.056*
C13	0.21185 (17)	0.96457 (16)	0.68549 (15)	0.0413 (3)
C14	0.1701 (2)	0.9614 (2)	0.82289 (17)	0.0541 (4)
H14	0.1102	1.0485	0.8415	0.065*
C15	0.2156 (2)	0.8347 (2)	0.92698 (17)	0.0596 (4)
H15	0.1890	0.8359	1.0161	0.071*
C16	0.3028 (2)	0.7010 (2)	0.90168 (15)	0.0545 (4)
H16	0.3306	0.6140	0.9742	0.065*
C17	0.34726 (19)	0.69747 (16)	0.77121 (13)	0.0422 (3)
H17	0.4051	0.6082	0.7558	0.051*
C18	0.30558 (16)	0.82910 (14)	0.65996 (12)	0.0344 (2)
C19	0.34334 (15)	0.83897 (12)	0.52100 (12)	0.0310 (2)
O1	0.67384 (13)	0.57343 (10)	0.60386 (9)	0.0374 (2)
O2	0.24447 (12)	0.73626 (10)	0.28658 (9)	0.0376 (2)
H2	0.268 (3)	0.630 (2)	0.317 (2)	0.066 (6)*
O3	0.32112 (19)	1.03639 (12)	0.17284 (11)	0.0592 (3)
N1	0.43075 (13)	0.72309 (10)	0.46469 (9)	0.0303 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0310 (5)	0.0265 (5)	0.0314 (5)	−0.0044 (4)	−0.0037 (4)	−0.0091 (4)
C2	0.0318 (5)	0.0332 (5)	0.0334 (5)	−0.0057 (4)	−0.0021 (4)	−0.0128 (4)
C3	0.0329 (6)	0.0468 (7)	0.0462 (7)	−0.0022 (5)	−0.0040 (5)	−0.0221 (6)
C4	0.0366 (6)	0.0628 (9)	0.0545 (8)	−0.0073 (6)	0.0071 (6)	−0.0317 (7)
C5	0.0490 (8)	0.0656 (9)	0.0402 (7)	−0.0176 (7)	0.0120 (6)	−0.0237 (7)
C6	0.0460 (7)	0.0487 (7)	0.0309 (6)	−0.0114 (5)	0.0016 (5)	−0.0106 (5)
C7	0.0339 (5)	0.0342 (5)	0.0308 (5)	−0.0075 (4)	−0.0004 (4)	−0.0096 (4)
C8	0.0328 (5)	0.0321 (5)	0.0268 (5)	−0.0041 (4)	−0.0038 (4)	−0.0057 (4)
C9	0.0367 (6)	0.0319 (5)	0.0370 (6)	−0.0045 (4)	−0.0026 (4)	−0.0040 (4)
C10	0.0323 (5)	0.0302 (5)	0.0430 (6)	−0.0053 (4)	−0.0014 (4)	−0.0104 (5)
C11	0.0384 (6)	0.0293 (6)	0.0628 (8)	−0.0041 (5)	−0.0020 (6)	−0.0146 (5)
C12	0.0378 (6)	0.0398 (7)	0.0697 (9)	−0.0068 (5)	0.0044 (6)	−0.0297 (7)
C13	0.0310 (5)	0.0490 (7)	0.0540 (7)	−0.0105 (5)	0.0038 (5)	−0.0301 (6)
C14	0.0438 (7)	0.0725 (10)	0.0611 (9)	−0.0126 (7)	0.0084 (6)	−0.0447 (9)
C15	0.0510 (8)	0.0929 (13)	0.0467 (8)	−0.0148 (8)	0.0065 (6)	−0.0413 (9)
C16	0.0540 (8)	0.0735 (10)	0.0354 (7)	−0.0126 (7)	0.0017 (6)	−0.0188 (7)
C17	0.0428 (7)	0.0495 (7)	0.0346 (6)	−0.0087 (5)	0.0009 (5)	−0.0158 (5)
C18	0.0290 (5)	0.0408 (6)	0.0379 (6)	−0.0088 (4)	0.0016 (4)	−0.0184 (5)
C19	0.0278 (5)	0.0304 (5)	0.0353 (5)	−0.0060 (4)	0.0001 (4)	−0.0119 (4)
O1	0.0403 (5)	0.0356 (4)	0.0330 (4)	−0.0006 (3)	−0.0097 (3)	−0.0091 (3)
O2	0.0338 (4)	0.0389 (5)	0.0380 (4)	−0.0049 (3)	−0.0085 (3)	−0.0089 (4)
O3	0.0753 (8)	0.0408 (6)	0.0421 (5)	−0.0017 (5)	−0.0040 (5)	0.0047 (4)
N1	0.0325 (5)	0.0292 (4)	0.0265 (4)	−0.0019 (3)	−0.0028 (3)	−0.0080 (3)

C1—O1	1.2192 (14)	C10—C19	1.3826 (16)
C1—N1	1.3908 (14)	C10—C11	1.4075 (17)
C1—C2	1.4829 (16)	C11—C12	1.359 (2)
C2—C3	1.3855 (16)	C11—H11	0.9300
C2—C7	1.3858 (16)	C12—C13	1.421 (2)
C3—C4	1.387 (2)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.420 (2)
C4—C5	1.393 (2)	C13—C18	1.4307 (17)
C4—H4	0.9300	C14—C15	1.349 (3)
C5—C6	1.387 (2)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.404 (3)
C6—C7	1.3885 (17)	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.3704 (18)
C7—C8	1.4983 (16)	C16—H16	0.9300
C8—O2	1.4071 (14)	C17—C18	1.4148 (19)
C8—N1	1.4905 (14)	C17—H17	0.9300
C8—C9	1.5445 (16)	C18—C19	1.4177 (16)
C9—O3	1.2037 (16)	C19—N1	1.4278 (14)
C9—C10	1.4616 (18)	O2—H2	0.96 (2)
O1—C1—N1	125.83 (10)	C11—C10—C9	127.75 (12)
O1—C1—C2	127.52 (10)	C12—C11—C10	118.08 (13)
N1—C1—C2	106.62 (9)	C12—C11—H11	121.0
C3—C2—C7	121.55 (11)	C10—C11—H11	121.0
C3—C2—C1	128.81 (11)	C11—C12—C13	121.64 (12)
C7—C2—C1	109.36 (10)	C11—C12—H12	119.2
C2—C3—C4	117.33 (12)	C13—C12—H12	119.2
C2—C3—H3	121.3	C14—C13—C12	120.91 (13)
C4—C3—H3	121.3	C14—C13—C18	118.03 (14)
C3—C4—C5	121.23 (13)	C12—C13—C18	121.06 (12)
C3—C4—H4	119.4	C15—C14—C13	121.45 (14)
C5—C4—H4	119.4	C15—C14—H14	119.3
C6—C5—C4	121.25 (12)	C13—C14—H14	119.3
C6—C5—H5	119.4	C14—C15—C16	120.45 (14)
C4—C5—H5	119.4	C14—C15—H15	119.8
C5—C6—C7	117.34 (13)	C16—C15—H15	119.8
C5—C6—H6	121.3	C17—C16—C15	120.69 (16)
C7—C6—H6	121.3	C17—C16—H16	119.7
C2—C7—C6	121.28 (11)	C15—C16—H16	119.7
C2—C7—C8	109.15 (10)	C16—C17—C18	120.21 (14)
C6—C7—C8	129.57 (11)	C16—C17—H17	119.9
O2—C8—N1	111.82 (9)	C18—C17—H17	119.9
O2—C8—C7	113.83 (9)	C17—C18—C19	125.32 (11)
N1—C8—C7	103.29 (9)	C17—C18—C13	119.13 (12)
O2—C8—C9	104.10 (9)	C19—C18—C13	115.52 (12)
N1—C8—C9	103.13 (9)	C10—C19—C18	121.92 (11)
C7—C8—C9	120.25 (10)	C10—C19—N1	109.84 (10)
O3—C9—C10	129.58 (12)	C18—C19—N1	128.21 (10)
O3—C9—C8	124.77 (12)	C8—O2—H2	107.6 (12)
C10—C9—C8	105.45 (9)	C1—N1—C19	126.89 (9)
C19—C10—C11	121.77 (12)	C1—N1—C8	111.06 (9)
C19—C10—C9	110.43 (10)	C19—N1—C8	108.74 (9)
O1—C1—C2—C3	1.8 (2)	C11—C12—C13—C18	−0.5 (2)
N1—C1—C2—C3	179.64 (12)	C12—C13—C14—C15	178.73 (14)
O1—C1—C2—C7	−172.16 (12)	C18—C13—C14—C15	−0.5 (2)
N1—C1—C2—C7	5.70 (13)	C13—C14—C15—C16	−1.3 (2)
C7—C2—C3—C4	1.3 (2)	C14—C15—C16—C17	1.6 (3)
C1—C2—C3—C4	−171.95 (12)	C15—C16—C17—C18	0.0 (2)
C2—C3—C4—C5	−0.3 (2)	C16—C17—C18—C19	−179.45 (13)
C3—C4—C5—C6	−1.2 (2)	C16—C17—C18—C13	−1.7 (2)
C4—C5—C6—C7	1.6 (2)	C14—C13—C18—C17	2.00 (18)
C3—C2—C7—C6	−0.90 (19)	C12—C13—C18—C17	−177.24 (12)
C1—C2—C7—C6	173.56 (11)	C14—C13—C18—C19	179.92 (11)
C3—C2—C7—C8	177.95 (11)	C12—C13—C18—C19	0.68 (17)
C1—C2—C7—C8	−7.60 (13)	C11—C10—C19—C18	0.37 (18)
C5—C6—C7—C2	−0.6 (2)	C9—C10—C19—C18	−177.05 (10)
C5—C6—C7—C8	−179.17 (13)	C11—C10—C19—N1	178.75 (11)
C2—C7—C8—O2	−115.06 (11)	C9—C10—C19—N1	1.33 (14)
C6—C7—C8—O2	63.66 (17)	C17—C18—C19—C10	177.17 (12)
C2—C7—C8—N1	6.39 (12)	C13—C18—C19—C10	−0.61 (17)
C6—C7—C8—N1	−174.89 (13)	C17—C18—C19—N1	−0.9 (2)
C2—C7—C8—C9	120.48 (11)	C13—C18—C19—N1	−178.66 (10)
C6—C7—C8—C9	−60.81 (18)	O1—C1—N1—C19	40.41 (18)
O2—C8—C9—O3	−72.49 (16)	C2—C1—N1—C19	−137.50 (11)
N1—C8—C9—O3	170.63 (13)	O1—C1—N1—C8	176.42 (11)
C7—C8—C9—O3	56.47 (18)	C2—C1—N1—C8	−1.48 (12)
O2—C8—C9—C10	102.75 (10)	C10—C19—N1—C1	125.80 (12)
N1—C8—C9—C10	−14.13 (12)	C18—C19—N1—C1	−55.95 (17)
C7—C8—C9—C10	−128.29 (11)	C10—C19—N1—C8	−11.01 (13)
O3—C9—C10—C19	−176.69 (14)	C18—C19—N1—C8	167.23 (11)
C8—C9—C10—C19	8.38 (13)	O2—C8—N1—C1	119.96 (10)
O3—C9—C10—C11	6.1 (2)	C7—C8—N1—C1	−2.84 (12)
C8—C9—C10—C11	−168.84 (12)	C9—C8—N1—C1	−128.76 (10)
C19—C10—C11—C12	−0.18 (19)	O2—C8—N1—C19	−95.95 (11)
C9—C10—C11—C12	176.77 (12)	C7—C8—N1—C19	141.25 (9)
C10—C11—C12—C13	0.3 (2)	C9—C8—N1—C19	15.33 (11)
C11—C12—C13—C14	−179.76 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.96 (2)	1.85 (2)	2.7978 (15)	172.2 (17)
C6—H6···O3ii	0.93	2.52	3.1609 (18)	126

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.96 (2)	1.85 (2)	2.7978 (15)	172.2 (17)
C6—H6⋯O3ii	0.93	2.52	3.1609 (18)	126

Symmetry codes: (i) ; (ii) .