6-[(2-Hy-droxy-eth-yl)amino]-7H-dibenzo[de,h]quinolin-7-one.

The title compound, C(18)H(14)N(2)O(2), is a new oxoisoaporphine derivative synthesized by alkyl-ation of 6-chloro-1-aza-benzanthrone. The oxoisoaporphine fragment deviates significantly from planarity with a dihedral angle of 5.1 (1)° between the heterocycle and the remote benzene ring. The amino and oxo groups are involved in an intra-molecular N-H⋯O hydrogen bond, while the hy-droxy groups form inter-molecular O-H⋯N hydrogen bonds, which link pairs of mol-ecules into inversion dimers. In the dimer, two approximately parallel oxoisoaporphine fragments exhibit π-π inter-actions between the aromatic rings, the shortest centroid-centroid distance being 3.649 (3) Å.

Related literature

For related oxoisoaporphine alkaloids, see: Tang et al. (2011 ▶, 2012 ▶). For background to the synthesis of 6-chloro-1-aza­benzanthrone, see: Iwashima et al. (1984 ▶).

Experimental

Crystal data

C18H14N2O2

M = 290.31

Monoclinic,

a = 9.8047 (16) Å

b = 12.865 (2) Å

c = 10.7623 (17) Å

β = 100.113 (2)°

V = 1336.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.37 × 0.23 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.966, T max = 0.985

6462 measured reflections

2359 independent reflections

1918 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.124

S = 1.06

2359 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024440/cv5299sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024440/cv5299Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812024440/cv5299Isup3.cml

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

C18H14N2O2	F(000) = 608
Mr = 290.31	Dx = 1.443 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8047 (16) Å	Cell parameters from 2722 reflections
b = 12.865 (2) Å	θ = 2.5–26.8°
c = 10.7623 (17) Å	µ = 0.10 mm−1
β = 100.113 (2)°	T = 296 K
V = 1336.4 (4) Å3	Rod, red
Z = 4	0.37 × 0.23 × 0.16 mm

Bruker APEXII CCD diffractometer	2359 independent reflections
Radiation source: fine-focus sealed tube	1918 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 25.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→11
Tmin = 0.966, Tmax = 0.985	k = −15→15
6462 measured reflections	l = −12→9

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0673P)2 + 0.2157P] where P = (Fo2 + 2Fc2)/3
2359 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 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
N1	0.21519 (14)	0.40120 (11)	−0.17380 (12)	0.0495 (4)
N2	0.12415 (13)	0.52517 (10)	0.35165 (12)	0.0458 (3)
H2A	0.0651	0.4763	0.3552	0.055*
O1	−0.01188 (13)	0.36243 (10)	0.25513 (11)	0.0577 (3)
O2	−0.07301 (12)	0.66500 (10)	0.43621 (12)	0.0619 (4)
H2	−0.0969	0.6421	0.3646	0.093*
C1	0.16539 (15)	0.39304 (11)	−0.06593 (14)	0.0388 (3)
C2	0.07454 (15)	0.30520 (11)	−0.05216 (14)	0.0392 (4)
C3	0.04876 (17)	0.22647 (12)	−0.14357 (15)	0.0476 (4)
H3	0.0925	0.2284	−0.2135	0.057*
C4	−0.04056 (18)	0.14653 (13)	−0.13055 (18)	0.0561 (5)
H4	−0.0573	0.0950	−0.1920	0.067*
C5	−0.10582 (19)	0.14211 (14)	−0.02650 (18)	0.0588 (5)
H5	−0.1679	0.0887	−0.0194	0.071*
C6	−0.07916 (17)	0.21610 (13)	0.06584 (16)	0.0510 (4)
H6	−0.1217	0.2118	0.1364	0.061*
C7	0.01172 (15)	0.29820 (11)	0.05497 (14)	0.0399 (4)
C8	0.04297 (15)	0.37373 (11)	0.15948 (14)	0.0407 (4)
C9	0.13798 (14)	0.45744 (10)	0.14699 (13)	0.0368 (3)
C10	0.17469 (14)	0.53226 (11)	0.24424 (14)	0.0396 (4)
C11	0.26736 (16)	0.61437 (12)	0.22536 (16)	0.0468 (4)
H11	0.2907	0.6641	0.2882	0.056*
C12	0.32171 (16)	0.62173 (12)	0.11914 (16)	0.0494 (4)
H12	0.3820	0.6760	0.1106	0.059*
C13	0.28866 (15)	0.54778 (12)	0.01932 (15)	0.0434 (4)
C14	0.34160 (18)	0.55268 (13)	−0.09252 (16)	0.0534 (4)
H14	0.4035	0.6050	−0.1044	0.064*
C15	0.30213 (18)	0.48015 (14)	−0.18484 (16)	0.0562 (5)
H15	0.3374	0.4858	−0.2593	0.067*
C16	0.19688 (14)	0.46567 (11)	0.03452 (13)	0.0374 (3)
C17	0.15778 (18)	0.59083 (13)	0.46331 (15)	0.0505 (4)
H17A	0.2545	0.6110	0.4737	0.061*
H17B	0.1456	0.5509	0.5370	0.061*
C18	0.06966 (18)	0.68764 (13)	0.45660 (17)	0.0532 (4)
H18A	0.0940	0.7261	0.5349	0.064*
H18B	0.0894	0.7315	0.3886	0.064*

	U11	U22	U33	U12	U13	U23
N1	0.0556 (8)	0.0503 (8)	0.0433 (8)	−0.0023 (6)	0.0104 (6)	−0.0005 (6)
N2	0.0481 (7)	0.0442 (7)	0.0446 (8)	−0.0034 (6)	0.0072 (6)	−0.0084 (6)
O1	0.0682 (8)	0.0605 (8)	0.0478 (7)	−0.0192 (6)	0.0193 (6)	−0.0059 (5)
O2	0.0572 (8)	0.0731 (9)	0.0567 (8)	0.0077 (6)	0.0140 (6)	−0.0070 (6)
C1	0.0393 (8)	0.0374 (7)	0.0381 (8)	0.0030 (6)	0.0019 (6)	0.0012 (6)
C2	0.0402 (8)	0.0349 (8)	0.0394 (8)	0.0036 (6)	−0.0015 (6)	0.0008 (6)
C3	0.0525 (9)	0.0430 (9)	0.0449 (9)	0.0018 (7)	0.0019 (7)	−0.0049 (7)
C4	0.0608 (11)	0.0433 (9)	0.0598 (11)	−0.0049 (8)	−0.0016 (8)	−0.0127 (8)
C5	0.0591 (11)	0.0458 (9)	0.0690 (12)	−0.0170 (8)	0.0046 (9)	−0.0057 (9)
C6	0.0518 (10)	0.0472 (9)	0.0530 (10)	−0.0097 (7)	0.0064 (7)	0.0011 (8)
C7	0.0400 (8)	0.0354 (8)	0.0418 (8)	0.0003 (6)	0.0002 (6)	0.0015 (6)
C8	0.0407 (8)	0.0400 (8)	0.0399 (8)	−0.0004 (6)	0.0031 (6)	0.0011 (6)
C9	0.0355 (7)	0.0348 (7)	0.0384 (8)	0.0027 (6)	0.0013 (6)	−0.0004 (6)
C10	0.0361 (7)	0.0381 (8)	0.0424 (8)	0.0052 (6)	0.0005 (6)	−0.0011 (6)
C11	0.0471 (9)	0.0406 (8)	0.0501 (9)	−0.0036 (7)	0.0012 (7)	−0.0089 (7)
C12	0.0468 (9)	0.0411 (9)	0.0585 (11)	−0.0104 (7)	0.0047 (7)	−0.0018 (7)
C13	0.0413 (8)	0.0399 (8)	0.0474 (9)	−0.0015 (6)	0.0037 (6)	0.0032 (7)
C14	0.0543 (10)	0.0533 (10)	0.0535 (10)	−0.0118 (8)	0.0121 (8)	0.0049 (8)
C15	0.0627 (10)	0.0601 (11)	0.0485 (10)	−0.0084 (8)	0.0171 (8)	0.0032 (8)
C16	0.0355 (7)	0.0340 (7)	0.0403 (8)	0.0041 (6)	0.0002 (6)	0.0038 (6)
C17	0.0547 (9)	0.0513 (9)	0.0430 (9)	0.0012 (7)	0.0016 (7)	−0.0062 (7)
C18	0.0599 (10)	0.0487 (9)	0.0503 (10)	0.0018 (7)	0.0081 (8)	−0.0074 (8)

N1—C1	1.340 (2)	C7—C8	1.477 (2)
N1—C15	1.345 (2)	C8—C9	1.446 (2)
N2—C10	1.338 (2)	C9—C10	1.421 (2)
N2—C17	1.458 (2)	C9—C16	1.434 (2)
N2—H2A	0.8600	C10—C11	1.431 (2)
O1—C8	1.2508 (18)	C11—C12	1.347 (2)
O2—C18	1.408 (2)	C11—H11	0.9300
O2—H2	0.8200	C12—C13	1.429 (2)
C1—C16	1.421 (2)	C12—H12	0.9300
C1—C2	1.462 (2)	C13—C14	1.393 (2)
C2—C7	1.402 (2)	C13—C16	1.416 (2)
C2—C3	1.404 (2)	C14—C15	1.368 (2)
C3—C4	1.374 (2)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.385 (3)	C17—C18	1.510 (2)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.368 (2)	C17—H17B	0.9700
C5—H5	0.9300	C18—H18A	0.9700
C6—C7	1.400 (2)	C18—H18B	0.9700
C6—H6	0.9300
C1—N1—C15	117.96 (14)	N2—C10—C11	120.90 (13)
C10—N2—C17	127.43 (14)	C9—C10—C11	118.72 (14)
C10—N2—H2A	116.3	C12—C11—C10	121.88 (14)
C17—N2—H2A	116.3	C12—C11—H11	119.1
C18—O2—H2	109.5	C10—C11—H11	119.1
N1—C1—C16	122.94 (14)	C11—C12—C13	121.34 (14)
N1—C1—C2	117.99 (13)	C11—C12—H12	119.3
C16—C1—C2	119.06 (13)	C13—C12—H12	119.3
C7—C2—C3	118.62 (14)	C14—C13—C16	118.32 (14)
C7—C2—C1	119.75 (13)	C14—C13—C12	123.34 (14)
C3—C2—C1	121.63 (14)	C16—C13—C12	118.34 (14)
C4—C3—C2	120.55 (16)	C15—C14—C13	119.71 (15)
C4—C3—H3	119.7	C15—C14—H14	120.1
C2—C3—H3	119.7	C13—C14—H14	120.1
C3—C4—C5	120.43 (15)	N1—C15—C14	123.62 (16)
C3—C4—H4	119.8	N1—C15—H15	118.2
C5—C4—H4	119.8	C14—C15—H15	118.2
C6—C5—C4	120.16 (16)	C13—C16—C1	117.40 (14)
C6—C5—H5	119.9	C13—C16—C9	120.74 (13)
C4—C5—H5	119.9	C1—C16—C9	121.86 (13)
C5—C6—C7	120.50 (16)	N2—C17—C18	113.18 (13)
C5—C6—H6	119.8	N2—C17—H17A	108.9
C7—C6—H6	119.8	C18—C17—H17A	108.9
C6—C7—C2	119.68 (14)	N2—C17—H17B	108.9
C6—C7—C8	118.86 (14)	C18—C17—H17B	108.9
C2—C7—C8	121.43 (13)	H17A—C17—H17B	107.8
O1—C8—C9	122.71 (14)	O2—C18—C17	112.42 (14)
O1—C8—C7	119.24 (13)	O2—C18—H18A	109.1
C9—C8—C7	118.04 (13)	C17—C18—H18A	109.1
C10—C9—C16	118.97 (13)	O2—C18—H18B	109.1
C10—C9—C8	121.34 (14)	C17—C18—H18B	109.1
C16—C9—C8	119.69 (13)	H18A—C18—H18B	107.9
N2—C10—C9	120.38 (13)
C15—N1—C1—C16	2.1 (2)	C16—C9—C10—N2	−178.32 (12)
C15—N1—C1—C2	−177.97 (14)	C8—C9—C10—N2	1.6 (2)
N1—C1—C2—C7	−175.08 (13)	C16—C9—C10—C11	1.1 (2)
C16—C1—C2—C7	4.8 (2)	C8—C9—C10—C11	−178.90 (13)
N1—C1—C2—C3	5.3 (2)	N2—C10—C11—C12	178.58 (14)
C16—C1—C2—C3	−174.74 (13)	C9—C10—C11—C12	−0.9 (2)
C7—C2—C3—C4	2.6 (2)	C10—C11—C12—C13	0.4 (2)
C1—C2—C3—C4	−177.84 (14)	C11—C12—C13—C14	179.55 (16)
C2—C3—C4—C5	−0.4 (3)	C11—C12—C13—C16	−0.1 (2)
C3—C4—C5—C6	−1.6 (3)	C16—C13—C14—C15	1.2 (2)
C4—C5—C6—C7	1.4 (3)	C12—C13—C14—C15	−178.41 (15)
C5—C6—C7—C2	0.8 (2)	C1—N1—C15—C14	−0.4 (3)
C5—C6—C7—C8	−177.12 (14)	C13—C14—C15—N1	−1.2 (3)
C3—C2—C7—C6	−2.7 (2)	C14—C13—C16—C1	0.3 (2)
C1—C2—C7—C6	177.68 (13)	C12—C13—C16—C1	179.97 (12)
C3—C2—C7—C8	175.10 (13)	C14—C13—C16—C9	−179.27 (13)
C1—C2—C7—C8	−4.5 (2)	C12—C13—C16—C9	0.4 (2)
C6—C7—C8—O1	0.3 (2)	N1—C1—C16—C13	−2.0 (2)
C2—C7—C8—O1	−177.57 (13)	C2—C1—C16—C13	178.04 (12)
C6—C7—C8—C9	179.47 (13)	N1—C1—C16—C9	177.53 (13)
C2—C7—C8—C9	1.6 (2)	C2—C1—C16—C9	−2.4 (2)
O1—C8—C9—C10	0.1 (2)	C10—C9—C16—C13	−0.9 (2)
C7—C8—C9—C10	−179.09 (12)	C8—C9—C16—C13	179.11 (12)
O1—C8—C9—C16	−179.94 (13)	C10—C9—C16—C1	179.52 (12)
C7—C8—C9—C16	0.9 (2)	C8—C9—C16—C1	−0.4 (2)
C17—N2—C10—C9	175.77 (13)	C10—N2—C17—C18	86.77 (19)
C17—N2—C10—C11	−3.7 (2)	N2—C17—C18—O2	56.18 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.90	2.5990 (17)	138
O2—H2···N1i	0.82	2.24	3.0434 (18)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.90	2.5990 (17)	138
O2—H2⋯N1i	0.82	2.24	3.0434 (18)	165

Symmetry code: (i) .