2-(Anthracen-9-yl)-10-meth-oxy-benzo[h]quinoline acetone hemisolvate.

The asymmetric unit of the title structure, C(28)H(19)NO·0.5C(3)H(6)O, comprises one 2-(anthracen-9-yl)-10-meth-oxy-benzo[h]-quinoline mol-ecule and an acteone mol-ecule with an occupany of 0.5. The solvent mol-ecule is disordered around a centre of symmetry. Its occupancy was determined from NMR data and kept fixed during the refinement. The two conjugated ring systems of the mol-ecule are almost perpendicular to each other; the inter-planar angle between the anthracene and quinoline ring systems is 84.9 (2)°.

Related literature

For the structure and synthesys of a related compound, see: Dong et al. (2011 ▶). For background information on quinoline derivatives, see: Kouznetsov et al. (2005 ▶); Maguire et al. (1994 ▶).

Experimental

Crystal data

C28H19NO·0.5C3H6O

M = 414.48

Triclinic,

a = 9.198 (3) Å

b = 10.690 (4) Å

c = 11.130 (4) Å

α = 95.224 (4)°

β = 91.484 (5)°

γ = 94.064 (5)°

V = 1086.6 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.977, T max = 0.985

4167 measured reflections

3688 independent reflections

2474 reflections with I > 2σ(I)

R int = 0.011

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.160

S = 1.01

3688 reflections

300 parameters

24 restraints

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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/S1600536812031807/fy2041sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812031807/fy2041Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812031807/fy2041Isup3.cml

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

C28H19NO·0.5C3H6O	Z = 2
Mr = 414.48	F(000) = 436
Triclinic, P1	Dx = 1.267 Mg m−3
a = 9.198 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.690 (4) Å	Cell parameters from 1500 reflections
c = 11.130 (4) Å	θ = 2.2–26.5°
α = 95.224 (4)°	µ = 0.08 mm−1
β = 91.484 (5)°	T = 293 K
γ = 94.064 (5)°	Block, yellow
V = 1086.6 (6) Å3	0.30 × 0.20 × 0.20 mm

Bruker SMART APEX CCD diffractometer	3688 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.011
φ and ω scan	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
Tmin = 0.977, Tmax = 0.985	k = −12→12
4167 measured reflections	l = −13→11

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.6424P] where P = (Fo2 + 2Fc2)/3
3688 reflections	(Δ/σ)max < 0.001
300 parameters	Δρmax = 0.58 e Å−3
24 restraints	Δρmin = −0.36 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
N1	0.9385 (2)	0.7649 (2)	0.19927 (19)	0.0487 (6)
O1	0.8308 (2)	0.55815 (19)	0.06758 (18)	0.0685 (6)
C1	1.0227 (3)	0.8273 (3)	0.2862 (2)	0.0523 (7)
C2	1.0377 (4)	0.9587 (3)	0.3040 (3)	0.0806 (11)
H2	1.0988	0.9996	0.3654	0.097*
C3	0.9605 (4)	1.0255 (3)	0.2293 (4)	0.0914 (12)
H3	0.9682	1.1131	0.2401	0.110*
C4	0.7849 (4)	1.0318 (3)	0.0594 (4)	0.0956 (12)
H4	0.7913	1.1194	0.0684	0.115*
C5	0.6963 (4)	0.9694 (4)	−0.0260 (4)	0.0922 (12)
H5	0.6413	1.0152	−0.0751	0.111*
C6	0.5836 (4)	0.7764 (4)	−0.1350 (3)	0.0862 (11)
H6	0.5299	0.8249	−0.1825	0.103*
C7	0.5664 (4)	0.6499 (5)	−0.1524 (3)	0.0912 (12)
H7	0.4987	0.6116	−0.2103	0.109*
C8	0.6485 (3)	0.5765 (4)	−0.0852 (3)	0.0751 (9)
H8	0.6364	0.4893	−0.0996	0.090*
C9	0.7480 (3)	0.6299 (3)	0.0028 (2)	0.0581 (7)
C10	0.8701 (3)	0.9638 (3)	0.1371 (3)	0.0717 (9)
C11	0.8621 (3)	0.8311 (3)	0.1236 (2)	0.0528 (7)
C12	0.6825 (3)	0.8358 (3)	−0.0450 (3)	0.0699 (9)
C13	0.7672 (3)	0.7633 (3)	0.0278 (2)	0.0555 (7)
C14	1.1068 (3)	0.7524 (2)	0.3671 (2)	0.0486 (7)
C15	1.0442 (3)	0.7100 (2)	0.4715 (2)	0.0510 (7)
C16	0.8982 (3)	0.7313 (3)	0.5034 (3)	0.0609 (8)
H16	0.8414	0.7761	0.4546	0.073*
C17	0.8410 (4)	0.6874 (3)	0.6035 (3)	0.0732 (9)
H17	0.7460	0.7034	0.6232	0.088*
C18	0.9233 (4)	0.6178 (3)	0.6782 (3)	0.0770 (9)
H18	0.8818	0.5871	0.7460	0.092*
C19	1.0615 (4)	0.5955 (3)	0.6525 (3)	0.0698 (9)
H19	1.1141	0.5486	0.7024	0.084*
C20	1.1291 (3)	0.6424 (3)	0.5499 (2)	0.0551 (7)
C21	1.2725 (3)	0.6238 (3)	0.5236 (3)	0.0606 (8)
H21	1.3280	0.5823	0.5763	0.073*
C22	1.3367 (3)	0.6650 (2)	0.4208 (3)	0.0535 (7)
C23	1.4854 (3)	0.6474 (3)	0.3929 (3)	0.0662 (8)
H23	1.5430	0.6078	0.4456	0.079*
C24	1.5438 (3)	0.6870 (3)	0.2919 (3)	0.0734 (9)
H24	1.6402	0.6736	0.2750	0.088*
C25	1.4589 (3)	0.7485 (3)	0.2122 (3)	0.0711 (9)
H25	1.4998	0.7750	0.1424	0.085*
C26	1.3194 (3)	0.7698 (3)	0.2352 (3)	0.0605 (8)
H26	1.2662	0.8117	0.1814	0.073*
C27	1.2511 (3)	0.7294 (2)	0.3405 (2)	0.0500 (7)
C28	0.8286 (4)	0.4265 (3)	0.0294 (3)	0.0799 (10)
H28A	0.7327	0.3877	0.0388	0.120*
H28B	0.8978	0.3882	0.0778	0.120*
H28C	0.8538	0.4154	−0.0538	0.120*
O2	0.6026 (8)	0.9238 (7)	0.5926 (7)	0.144 (2)	0.50
C29	0.529 (2)	0.9719 (13)	0.5379 (16)	0.165 (3)	0.50
C30	0.3978 (8)	0.9798 (6)	0.5752 (6)	0.173 (3)
H30A	0.3522	0.8966	0.5787	0.260*
H30B	0.3429	1.0240	0.5203	0.260*
H30C	0.4007	1.0245	0.6541	0.260*

	U11	U22	U33	U12	U13	U23
N1	0.0432 (12)	0.0504 (13)	0.0536 (14)	0.0073 (10)	−0.0003 (10)	0.0094 (11)
O1	0.0708 (14)	0.0658 (14)	0.0672 (13)	0.0075 (10)	−0.0151 (11)	−0.0006 (11)
C1	0.0477 (16)	0.0492 (17)	0.0597 (18)	0.0056 (13)	−0.0055 (13)	0.0038 (13)
C2	0.084 (2)	0.0502 (19)	0.104 (3)	0.0075 (17)	−0.033 (2)	−0.0007 (18)
C3	0.098 (3)	0.0456 (19)	0.130 (3)	0.0118 (18)	−0.027 (2)	0.012 (2)
C4	0.089 (3)	0.070 (2)	0.133 (4)	0.012 (2)	−0.020 (3)	0.044 (2)
C5	0.073 (2)	0.102 (3)	0.111 (3)	0.013 (2)	−0.017 (2)	0.059 (3)
C6	0.065 (2)	0.133 (4)	0.065 (2)	0.013 (2)	−0.0119 (17)	0.034 (2)
C7	0.071 (2)	0.133 (4)	0.069 (2)	0.008 (2)	−0.0160 (18)	0.009 (2)
C8	0.062 (2)	0.098 (3)	0.063 (2)	0.0026 (18)	−0.0064 (16)	−0.0007 (18)
C9	0.0472 (17)	0.079 (2)	0.0489 (17)	0.0050 (15)	0.0015 (13)	0.0065 (15)
C10	0.066 (2)	0.061 (2)	0.091 (2)	0.0084 (16)	−0.0095 (18)	0.0239 (18)
C11	0.0435 (15)	0.0582 (18)	0.0600 (17)	0.0074 (13)	0.0043 (13)	0.0191 (14)
C12	0.0557 (19)	0.094 (3)	0.066 (2)	0.0079 (17)	0.0020 (15)	0.0356 (18)
C13	0.0417 (15)	0.076 (2)	0.0515 (17)	0.0061 (14)	0.0047 (12)	0.0193 (15)
C14	0.0499 (16)	0.0417 (15)	0.0531 (16)	0.0053 (12)	−0.0082 (13)	−0.0011 (12)
C15	0.0535 (17)	0.0431 (15)	0.0547 (17)	0.0050 (12)	−0.0056 (13)	−0.0032 (13)
C16	0.0544 (18)	0.0600 (19)	0.068 (2)	0.0064 (14)	−0.0024 (15)	0.0010 (15)
C17	0.063 (2)	0.078 (2)	0.077 (2)	0.0023 (17)	0.0109 (17)	0.0006 (18)
C18	0.087 (3)	0.081 (2)	0.062 (2)	−0.001 (2)	0.0133 (18)	0.0083 (18)
C19	0.084 (2)	0.071 (2)	0.0567 (19)	0.0106 (17)	−0.0004 (17)	0.0108 (16)
C20	0.0614 (19)	0.0514 (17)	0.0523 (17)	0.0072 (14)	−0.0043 (14)	0.0022 (13)
C21	0.0648 (19)	0.0574 (18)	0.0607 (19)	0.0163 (14)	−0.0147 (15)	0.0072 (14)
C22	0.0546 (17)	0.0458 (16)	0.0593 (18)	0.0085 (13)	−0.0083 (14)	−0.0002 (13)
C23	0.0550 (19)	0.0616 (19)	0.082 (2)	0.0140 (15)	−0.0098 (16)	0.0014 (17)
C24	0.0534 (19)	0.074 (2)	0.093 (3)	0.0103 (16)	0.0082 (18)	0.0024 (19)
C25	0.064 (2)	0.075 (2)	0.077 (2)	0.0077 (17)	0.0115 (17)	0.0099 (17)
C26	0.0601 (19)	0.0588 (18)	0.0633 (19)	0.0075 (14)	−0.0011 (15)	0.0071 (15)
C27	0.0516 (16)	0.0428 (15)	0.0550 (17)	0.0053 (12)	−0.0041 (13)	0.0006 (13)
C28	0.086 (2)	0.068 (2)	0.083 (2)	0.0024 (18)	−0.0104 (19)	−0.0057 (18)
O2	0.139 (5)	0.144 (5)	0.149 (5)	0.022 (4)	−0.012 (4)	0.018 (4)
C29	0.202 (5)	0.118 (4)	0.164 (5)	−0.002 (4)	−0.041 (5)	−0.026 (4)
C30	0.213 (5)	0.123 (3)	0.171 (5)	−0.003 (4)	−0.044 (4)	−0.027 (3)

N1—C1	1.323 (3)	C16—C17	1.352 (4)
N1—C11	1.362 (3)	C16—H16	0.9300
O1—C9	1.358 (3)	C17—C18	1.406 (4)
O1—C28	1.431 (3)	C17—H17	0.9300
C1—C2	1.397 (4)	C18—C19	1.343 (4)
C1—C14	1.495 (3)	C18—H18	0.9300
C2—C3	1.362 (4)	C19—C20	1.428 (4)
C2—H2	0.9300	C19—H19	0.9300
C3—C10	1.391 (5)	C20—C21	1.383 (4)
C3—H3	0.9300	C21—C22	1.393 (4)
C4—C5	1.334 (5)	C21—H21	0.9300
C4—C10	1.433 (4)	C22—C27	1.431 (3)
C4—H4	0.9300	C22—C23	1.432 (4)
C5—C12	1.420 (5)	C23—C24	1.348 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.346 (5)	C24—C25	1.404 (4)
C6—C12	1.411 (5)	C24—H24	0.9300
C6—H6	0.9300	C25—C26	1.346 (4)
C7—C8	1.381 (5)	C25—H25	0.9300
C7—H7	0.9300	C26—C27	1.430 (4)
C8—C9	1.379 (4)	C26—H26	0.9300
C8—H8	0.9300	C28—H28A	0.9600
C9—C13	1.425 (4)	C28—H28B	0.9600
C10—C11	1.409 (4)	C28—H28C	0.9600
C11—C13	1.464 (4)	O2—C29	1.083 (13)
C12—C13	1.425 (4)	C29—C29i	1.22 (3)
C14—C27	1.401 (4)	C29—C30	1.30 (2)
C14—C15	1.407 (4)	C30—H30A	0.9600
C15—C16	1.426 (4)	C30—H30B	0.9600
C15—C20	1.433 (4)	C30—H30C	0.9600
C1—N1—C11	118.9 (2)	C15—C16—H16	119.5
C9—O1—C28	117.7 (2)	C16—C17—C18	120.9 (3)
N1—C1—C2	123.1 (3)	C16—C17—H17	119.6
N1—C1—C14	117.8 (2)	C18—C17—H17	119.6
C2—C1—C14	119.1 (2)	C19—C18—C17	120.5 (3)
C3—C2—C1	118.4 (3)	C19—C18—H18	119.8
C3—C2—H2	120.8	C17—C18—H18	119.8
C1—C2—H2	120.8	C18—C19—C20	121.2 (3)
C2—C3—C10	120.5 (3)	C18—C19—H19	119.4
C2—C3—H3	119.8	C20—C19—H19	119.4
C10—C3—H3	119.8	C21—C20—C19	122.2 (3)
C5—C4—C10	119.9 (3)	C21—C20—C15	119.3 (3)
C5—C4—H4	120.0	C19—C20—C15	118.4 (3)
C10—C4—H4	120.0	C20—C21—C22	122.3 (3)
C4—C5—C12	122.7 (3)	C20—C21—H21	118.9
C4—C5—H5	118.6	C22—C21—H21	118.9
C12—C5—H5	118.6	C21—C22—C27	118.6 (3)
C7—C6—C12	120.4 (3)	C21—C22—C23	122.9 (3)
C7—C6—H6	119.8	C27—C22—C23	118.5 (3)
C12—C6—H6	119.8	C24—C23—C22	121.5 (3)
C6—C7—C8	120.6 (3)	C24—C23—H23	119.3
C6—C7—H7	119.7	C22—C23—H23	119.3
C8—C7—H7	119.7	C23—C24—C25	120.0 (3)
C9—C8—C7	121.3 (4)	C23—C24—H24	120.0
C9—C8—H8	119.3	C25—C24—H24	120.0
C7—C8—H8	119.3	C26—C25—C24	121.0 (3)
O1—C9—C8	121.5 (3)	C26—C25—H25	119.5
O1—C9—C13	118.0 (2)	C24—C25—H25	119.5
C8—C9—C13	120.5 (3)	C25—C26—C27	121.6 (3)
C3—C10—C11	118.0 (3)	C25—C26—H26	119.2
C3—C10—C4	121.5 (3)	C27—C26—H26	119.2
C11—C10—C4	120.5 (3)	C14—C27—C26	122.5 (2)
N1—C11—C10	121.2 (3)	C14—C27—C22	120.1 (3)
N1—C11—C13	119.5 (3)	C26—C27—C22	117.4 (3)
C10—C11—C13	119.3 (2)	O1—C28—H28A	109.5
C6—C12—C5	119.5 (3)	O1—C28—H28B	109.5
C6—C12—C13	120.7 (3)	H28A—C28—H28B	109.5
C5—C12—C13	119.8 (3)	O1—C28—H28C	109.5
C12—C13—C9	116.5 (3)	H28A—C28—H28C	109.5
C12—C13—C11	117.7 (3)	H28B—C28—H28C	109.5
C9—C13—C11	125.7 (2)	C29i—C29—O2	167 (4)
C27—C14—C15	120.3 (2)	C29i—C29—C30	76.3 (19)
C27—C14—C1	119.1 (2)	O2—C29—C30	117 (2)
C15—C14—C1	120.5 (2)	C29—C30—H30A	109.5
C14—C15—C16	122.7 (2)	C29—C30—H30B	109.5
C14—C15—C20	119.4 (2)	H30A—C30—H30B	109.5
C16—C15—C20	117.9 (3)	C29—C30—H30C	109.5
C17—C16—C15	121.0 (3)	H30A—C30—H30C	109.5
C17—C16—H16	119.5	H30B—C30—H30C	109.5