2-(Anthracen-9-yl)-10-meth­oxy­benzo[h]quinoline acetone hemisolvate

Dong, Z.; Liu, B.; Cui, X.; Liu, Y.

doi:10.1107/S1600536812031807

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2535

https://doi.org/10.1107/S1600536812031807

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2-(Anthracen-9-yl)-10-methoxybenzo[h]quinoline acetone hemisolvate

Zhenming Dong,^a Bo Liu,^b ^* Xinxin Cui ^a and Yufang Liu ^a

^aSchool of Chemistry and Chemical Engineering, Shanxi University, Taiyuan 030006, People's Republic of China, and ^bInstitute of Chemistry, School of Science, Beijing Jiaotong University, Beijing 100044, People's Republic of China
^*Correspondence e-mail: liubo4314@yahoo.com.cn

(Received 10 January 2012; accepted 12 July 2012; online 25 July 2012)

The asymmetric unit of the title structure, C₂₈H₁₉NO·0.5C₃H₆O, comprises one 2-(anthracen-9-yl)-10-methoxybenzo[h]quinoline molecule and an acteone molecule with an occupany of 0.5. The solvent molecule 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 molecule are almost perpendicular to each other; the interplanar 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_r = 414.48
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.160
S = 1.01
3688 reflections
300 parameters
24 restraints
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812031807/fy2041sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031807/fy2041Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031807/fy2041Isup3.cml

checkCIF report

Comment top

Quinoline derivatives represent a major class of heterocycles, and a number of preparations have been known since the late 1800s (Kouznetsov et al., 2005). The quinoline ring system occurs in various natural products, especially in alkaloids (Kouznetsov et al., 2005). Some 3-substituted quinoline derivatives can be used as Platelet-derived growth factor (PDGF) receptors (Maguire et al., 1994). In the course of exploring new quinoline derivatives, we obtained the title compound (I), and the synthesis and structure are reported here.

Related literature top

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 top

The precursor MBQ (10-methoxybenzo[h]quinoline) was synthesized according to Dong et al. (2011). Under a nitrogen atmosphere and at -78°C, a solution of n-butyllithium (0.16 mol) in anhydrous n-hexane (100 ml) was added portionwise with stirring to a solution of 9-bromoanthracene(14.5 g, 56.3 mmol) in anhydrous tetrahydrofuran (100 ml), and stirring continued for 50 min to form 9-Lithiumanthracene. Then a solution of MBQ (7.85 g, 37.5 mmol) in tetrahydrofuran (75 ml) was added dropwise with stirring over 2 h and the mixture was stirred for another 3 h. The resulting orange reaction mixture was poured over 400 g crushed ice and neutralised with 6 M HCl solution, and then the organic solvents, n-hexane and tetrahydrofuran, were removed by evaporation to give the crude product of the title compound as a dark-red solid (11.1 g). The crude product was collected by filtration and then washed well with a hot ethanol-water mixture (1/1 v/v). Finally, recrystallization from acetone gave a pure sample of the title compound as yellow crystals (3.1 g; yield 40.0% based on MBQ). ¹H NMR (300 MHz, CDCl₃): δ 7.87-7.17 (m, 16H; benzo[h]quinoline and anthracen rings), 3.86, 3.81 (d, 3H; OCH₃), 2.18 (s, 3H; [(CH₃)₂CO]_0.5).

Structure description top

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).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Suffix A in the atom labels indicates symmetry (i) –x+1, –y+2, –z+1.

2-(Anthracen-9-yl)-10-methoxybenzo[h]quinoline acetone hemisolvate top

Crystal data top

C₂₈H₁₉NO·0.5C₃H₆O	Z = 2
M_r = 414.48	F(000) = 436
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0496P)² + 0.6424P] where P = (F_o² + 2F_c²)/3
3688 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.58 e Å⁻³
24 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₈H₁₉NO·0.5C₃H₆O	γ = 94.064 (5)°
M_r = 414.48	V = 1086.6 (6) Å³
Triclinic, P1	Z = 2
a = 9.198 (3) Å	Mo Kα radiation
b = 10.690 (4) Å	µ = 0.08 mm⁻¹
c = 11.130 (4) Å	T = 293 K
α = 95.224 (4)°	0.30 × 0.20 × 0.20 mm
β = 91.484 (5)°

Data collection top

Bruker SMART APEX CCD diffractometer	3688 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2474 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.985	R_int = 0.011
4167 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	24 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.01	Δρ_max = 0.58 e Å⁻³
3688 reflections	Δρ_min = −0.35 e Å⁻³
300 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₉NO·0.5C₃H₆O
M_r	414.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.198 (3), 10.690 (4), 11.130 (4)
α, β, γ (°)	95.224 (4), 91.484 (5), 94.064 (5)
V (Å³)	1086.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.977, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4167, 3688, 2474
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.160, 1.01
No. of reflections	3688
No. of parameters	300
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.35

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to the National Science Foundation (grant No. 21072019) for the support of this work.

References

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