4-(6-Benzyl-7-oxo-1,2,3,4,5,5a,5a1,6,7,7a,8,12b-dodeca­hydro­benzo[f]cyclo­octa­[cd]isoindol-8-yl)benzonitrile

Zhang, Y.-L.; Hu, Y.-M.

doi:10.1107/S1600536813006880

organic compounds

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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Page o550

doi:10.1107/S1600536813006880

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4-(6-Benzyl-7-oxo-1,2,3,4,5,5a,5a¹,6,7,7a,8,12b-dodecahydrobenzo[f]cycloocta[cd]isoindol-8-yl)benzonitrile

Yu-Long Zhang ^a and Yi-Min Hu ^a ^*

^aSchool of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, People's Republic of China
^*Correspondence e-mail: yiminhu@yahoo.cn

(Received 9 March 2013; accepted 12 March 2013; online 16 March 2013)

In the title compound, C₃₁H₃₀N₂O, the cis-fused cyclohexene and cyclooctane rings adopt boat and boat-chair conformations, respectively. The essentially planar five-membered N-heterocyclic ring [r.m.s. deviation = 0.017 (1) Å] is cis- and trans-fused, respectively, with the cyclohexene and cyclooctane rings. In the crystal, molecules are linked into inversion dimers through pairs of weak C—H⋯O interactions.

Related literature

For the atom economy and environmental benefits of using a domino reaction to construct a structurally complicated molecule, see: Zhao et al. (2012 ). For palladium-catalysed coupling reactions, see: Hu et al. (2009 , 2010 ). For the use of condensed heterocyclic compounds as synthetic building blocks, pharmacophores and electroluminescent materials, see: Rixson et al. (2012 ). For reactions of aryl halides with olefins, see: Yu & Hu (2012 ); Wang & Hu (2011 ).

Experimental

Crystal data

C₃₁H₃₀N₂O
M_r = 446.57
Monoclinic, P 2₁ /c
a = 10.0270 (11) Å
b = 11.2196 (13) Å
c = 21.445 (2) Å
β = 102.912 (1)°
V = 2351.5 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 291 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.981, T_max = 0.985
19941 measured reflections
5413 independent reflections
4118 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.128
S = 1.04
5413 reflections
308 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C29—H29⋯O1ⁱ	0.93	2.58	3.301 (2)	134
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 global, I. DOI: 10.1107/S1600536813006880/is5255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813006880/is5255Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813006880/is5255Isup3.cml

checkCIF report

Comment top

Domino reaction as an efficient protocol to construct structurally complicate molecule due to high atom economy and environmental benefits (Zhao et al., 2012). Palladium-catalyzed domino reactions have become an important tool of modern organic synthesis chemistry (Hu et al., 2009, 2010). Condensed heterocyclic compounds are playing increasingly important roles as synthetic building blocks, pharmacophores, and electroluminescence materials (Rixson et al., 2012). We have reported some novel intermolecular and intramolecular reactions of aryl halides with the olefins (Yu et al., 2012; Wang et al., 2011). The reaction of 4-bromobenzonitrile with N-benzyl-N-(cyclooct-2-en-1-yl) cinnamamide, in the presence of palladium(II) acetate and triphenylphosphine, in DMF at 423 K for 18 h, gave the unexpected title product.

The title compound, C₃₁H₃₀N₂O, contains three phenyl ring, one five-numbered N-heterocyclic ring, one six-membered carbon ring with a boat conformation, and one eight-memmbered carbon ring with a boat-chair conformation. All the rings are not coplanar (Fig. 1). In the molecule there are five chiral carbon atoms, C8, C14, C15, C16 and C18, but the crystal is a racemic system due to lacking of the chiral separation. In the crystal packing, there are weak intermolecular C—H···O interactions, C29—H29···O1ⁱ (i: -x, 1 - y, 1 - z), through which dimers were formed between paired enantiomers (Fig. 2).

Related literature top

For the atom economy and environmental benefits of using a domino reaction to construct astructurally complicated molecule, see: Zhao et al. (2012). For palladium-catalysed coupling reactions, see: Hu et al. (2009, 2010). For the use of condensed heterocyclic compounds as synthetic building blocks, pharmacophores and electroluminescent materials, see: Rixson et al. (2012). For reactions of aryl halides with olefins, see: Yu & Hu (2012); Wang & Hu (2011).

Experimental top

An oven-dried Schlenk flask was evacuated, filled with nitrogen, and then charged with N-benzyl-N-(cyclooct-2-en-1-yl)cinnamamide (3.45 g, 10 mmol), ethyl 4-bromobenzonitrile (2.01 g, 11 mmol), tributylamine (3 ml), PPh₃ (52.5 mg, 0.2 mmol), Pd(OAc)₂ (24 mg, 0.1 mol), and DMF (10 ml) to give a yellow solution. The reaction mixture was heated at 423 K with stirring. The reaction mixture was cooled to room temperature after 18 h and the resultant yellow-orange mixture was diluted with Et₂O (10 ml). The mixture was washed with H₂O (15 ml) and the aqueous layer was extracted with Et₂O (20 ml). The combined organic layers were dried (MgSO₄), filtered, and concentrated in vacuo. The crude material was purified by flash column chromatography on silica gel (petroleum ester:EtOAc, 8:1) and recrystallized from EtOAc, yield 3.48 g (78%). Colorless crystals suitable for X-ray diffraction were obtained by recrystallization from a solution of the title compound from ethyl acetate over a period of one week.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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, showing the atom-numbering scheme and displacement ellipsoids drawn at 30% probability level.
	Fig. 2. A view of a pair of racemic molecules linked by C—H···O hydrogen bonds shown as dashed lines [symmetry code (i): -x, 1 - y,1 - z].
	Fig. 3. A view of the cell packing down the a axis.

4-[3-Benzyl-2-oxo-3-azatetracyclo[8.7.1.0^4,18.0^11,16]octadeca-11 (16),12,14-trien-17-yl]benzonitrile top

Crystal data top

C₃₁H₃₀N₂O	F(000) = 952
M_r = 446.57	D_x = 1.261 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.0270 (11) Å	Cell parameters from 3715 reflections
b = 11.2196 (13) Å	θ = 2.1–23.7°
c = 21.445 (2) Å	µ = 0.08 mm⁻¹
β = 102.912 (1)°	T = 291 K
V = 2351.5 (5) Å³	Block, colourless
Z = 4	0.26 × 0.22 × 0.20 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5413 independent reflections
Radiation source: sealed tube	4118 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→11
T_min = 0.981, T_max = 0.985	k = −14→14
19941 measured reflections	l = −27→27

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.128	w = 1/[σ²(F_o²) + (0.0539P)² + 0.5346P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5413 reflections	Δρ_max = 0.23 e Å⁻³
308 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0045 (9)

Crystal data top

C₃₁H₃₀N₂O	V = 2351.5 (5) Å³
M_r = 446.57	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0270 (11) Å	µ = 0.08 mm⁻¹
b = 11.2196 (13) Å	T = 291 K
c = 21.445 (2) Å	0.26 × 0.22 × 0.20 mm
β = 102.912 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	5413 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4118 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.985	R_int = 0.024
19941 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
5413 reflections	Δρ_min = −0.18 e Å⁻³
308 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.31111 (17)	0.90193 (14)	0.37306 (8)	0.0602 (4)
H1	0.2667	0.8293	0.3738	0.072*
C2	0.24286 (19)	0.99559 (15)	0.33757 (9)	0.0678 (5)
H2	0.1537	0.9853	0.3140	0.081*
C3	0.3070 (2)	1.10362 (15)	0.33714 (8)	0.0669 (5)
H3	0.2611	1.1668	0.3136	0.080*
C4	0.4377 (2)	1.11816 (15)	0.37124 (8)	0.0663 (5)
H4	0.4807	1.1916	0.3711	0.080*
C5	0.50674 (18)	1.02485 (14)	0.40593 (7)	0.0571 (4)
H5	0.5964	1.0357	0.4286	0.069*
C6	0.44428 (15)	0.91508 (12)	0.40739 (7)	0.0471 (3)
C7	0.52446 (15)	0.81721 (13)	0.44731 (7)	0.0516 (4)
H7A	0.6166	0.8170	0.4402	0.062*
H7B	0.5310	0.8355	0.4921	0.062*
C8	0.47447 (14)	0.63044 (12)	0.37700 (6)	0.0419 (3)
H8	0.4309	0.6764	0.3391	0.050*
C9	0.62199 (15)	0.60282 (15)	0.37396 (7)	0.0547 (4)
H9A	0.6612	0.5507	0.4094	0.066*
H9B	0.6738	0.6766	0.3799	0.066*
C10	0.64000 (18)	0.54450 (16)	0.31205 (8)	0.0635 (4)
H10A	0.7367	0.5447	0.3121	0.076*
H10B	0.5941	0.5937	0.2765	0.076*
C11	0.5869 (2)	0.41688 (16)	0.29973 (9)	0.0690 (5)
H11A	0.6509	0.3730	0.2806	0.083*
H11B	0.5875	0.3801	0.3407	0.083*
C12	0.4439 (2)	0.40138 (15)	0.25704 (8)	0.0683 (5)
H12A	0.4540	0.3974	0.2131	0.082*
H12B	0.4097	0.3245	0.2670	0.082*
C13	0.33303 (18)	0.49374 (14)	0.25950 (7)	0.0580 (4)
H13A	0.2574	0.4798	0.2232	0.070*
H13B	0.3699	0.5719	0.2538	0.070*
C14	0.27571 (15)	0.49744 (12)	0.31984 (6)	0.0460 (3)
H14	0.2353	0.4191	0.3239	0.055*
C15	0.38769 (13)	0.51737 (11)	0.38128 (6)	0.0391 (3)
H15	0.4489	0.4482	0.3872	0.047*
C16	0.33156 (13)	0.53197 (12)	0.44200 (6)	0.0406 (3)
H16	0.3689	0.4681	0.4720	0.049*
C17	0.38781 (13)	0.65000 (13)	0.47065 (6)	0.0450 (3)
C18	0.17476 (13)	0.53146 (13)	0.43172 (7)	0.0453 (3)
H18	0.1529	0.5725	0.4685	0.054*
C19	0.11444 (14)	0.60591 (13)	0.37323 (8)	0.0507 (4)
C20	0.16338 (15)	0.58891 (13)	0.31758 (7)	0.0507 (4)
C21	0.10974 (18)	0.65907 (16)	0.26432 (9)	0.0703 (5)
H21	0.1408	0.6488	0.2269	0.084*
C22	0.0109 (2)	0.74376 (19)	0.26639 (13)	0.0890 (7)
H22	−0.0241	0.7898	0.2304	0.107*
C23	−0.03587 (19)	0.76050 (17)	0.32073 (14)	0.0881 (7)
H23	−0.1027	0.8176	0.3216	0.106*
C24	0.01611 (16)	0.69246 (15)	0.37492 (10)	0.0688 (5)
H24	−0.0148	0.7048	0.4122	0.083*
C25	0.11027 (13)	0.40779 (13)	0.42908 (6)	0.0441 (3)
C26	0.18459 (16)	0.30341 (14)	0.43995 (9)	0.0601 (4)
H26	0.2795	0.3070	0.4474	0.072*
C27	0.12197 (17)	0.19377 (15)	0.44006 (9)	0.0638 (4)
H27	0.1746	0.1249	0.4480	0.077*
C28	−0.01900 (16)	0.18671 (15)	0.42841 (7)	0.0542 (4)
C29	−0.09470 (17)	0.28951 (17)	0.41747 (10)	0.0696 (5)
H29	−0.1896	0.2857	0.4097	0.083*
C30	−0.03091 (16)	0.39835 (16)	0.41795 (9)	0.0640 (4)
H30	−0.0838	0.4672	0.4106	0.077*
C31	−0.08463 (18)	0.07266 (18)	0.42638 (9)	0.0673 (5)
N1	0.46710 (11)	0.69837 (10)	0.43443 (5)	0.0433 (3)
N2	−0.13830 (19)	−0.01797 (17)	0.42320 (10)	0.0922 (6)
O1	0.36647 (12)	0.69285 (11)	0.52002 (5)	0.0644 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0559 (9)	0.0417 (8)	0.0776 (11)	−0.0027 (7)	0.0031 (8)	0.0007 (7)
C2	0.0631 (10)	0.0535 (10)	0.0794 (12)	0.0063 (8)	−0.0001 (9)	0.0033 (8)
C3	0.0878 (13)	0.0482 (9)	0.0634 (10)	0.0093 (9)	0.0141 (9)	0.0054 (7)
C4	0.0908 (13)	0.0451 (9)	0.0639 (10)	−0.0122 (9)	0.0191 (9)	0.0016 (7)
C5	0.0640 (10)	0.0516 (9)	0.0544 (8)	−0.0130 (7)	0.0106 (7)	−0.0045 (7)
C6	0.0526 (8)	0.0411 (7)	0.0471 (7)	−0.0036 (6)	0.0102 (6)	−0.0070 (6)
C7	0.0495 (8)	0.0442 (8)	0.0555 (8)	−0.0061 (6)	−0.0004 (6)	−0.0057 (6)
C8	0.0455 (7)	0.0393 (7)	0.0382 (6)	−0.0019 (5)	0.0038 (5)	0.0030 (5)
C9	0.0480 (8)	0.0619 (10)	0.0555 (8)	−0.0054 (7)	0.0146 (7)	0.0011 (7)
C10	0.0635 (10)	0.0703 (11)	0.0631 (10)	−0.0019 (8)	0.0278 (8)	0.0019 (8)
C11	0.0844 (13)	0.0600 (10)	0.0724 (11)	0.0088 (9)	0.0387 (10)	−0.0005 (8)
C12	0.1055 (15)	0.0502 (9)	0.0566 (9)	−0.0090 (9)	0.0340 (10)	−0.0083 (7)
C13	0.0795 (11)	0.0511 (9)	0.0393 (7)	−0.0151 (8)	0.0047 (7)	−0.0010 (6)
C14	0.0545 (8)	0.0376 (7)	0.0409 (7)	−0.0072 (6)	0.0003 (6)	0.0021 (5)
C15	0.0404 (7)	0.0355 (6)	0.0392 (6)	0.0019 (5)	0.0043 (5)	0.0033 (5)
C16	0.0365 (6)	0.0431 (7)	0.0394 (6)	0.0023 (5)	0.0027 (5)	0.0048 (5)
C17	0.0376 (7)	0.0508 (8)	0.0425 (7)	0.0027 (6)	0.0004 (5)	−0.0019 (6)
C18	0.0375 (7)	0.0472 (8)	0.0497 (7)	0.0024 (6)	0.0069 (6)	−0.0027 (6)
C19	0.0364 (7)	0.0407 (7)	0.0673 (9)	0.0001 (6)	−0.0047 (6)	0.0016 (6)
C20	0.0464 (8)	0.0426 (8)	0.0527 (8)	−0.0058 (6)	−0.0113 (6)	0.0043 (6)
C21	0.0655 (10)	0.0621 (10)	0.0660 (10)	−0.0076 (8)	−0.0222 (8)	0.0158 (8)
C22	0.0660 (12)	0.0685 (13)	0.1081 (17)	0.0023 (10)	−0.0324 (12)	0.0303 (12)
C23	0.0484 (10)	0.0549 (11)	0.143 (2)	0.0107 (8)	−0.0176 (12)	0.0156 (12)
C24	0.0421 (8)	0.0520 (9)	0.1047 (14)	0.0058 (7)	0.0003 (8)	0.0016 (9)
C25	0.0382 (7)	0.0522 (8)	0.0423 (7)	0.0001 (6)	0.0096 (5)	0.0011 (6)
C26	0.0398 (8)	0.0537 (9)	0.0840 (11)	−0.0010 (7)	0.0076 (7)	0.0076 (8)
C27	0.0518 (9)	0.0540 (10)	0.0843 (12)	0.0005 (7)	0.0126 (8)	0.0082 (8)
C28	0.0518 (9)	0.0606 (10)	0.0515 (8)	−0.0116 (7)	0.0146 (7)	0.0023 (7)
C29	0.0383 (8)	0.0788 (12)	0.0914 (13)	−0.0076 (8)	0.0141 (8)	0.0062 (10)
C30	0.0410 (8)	0.0610 (10)	0.0895 (12)	0.0039 (7)	0.0136 (8)	0.0065 (9)
C31	0.0589 (10)	0.0736 (12)	0.0691 (11)	−0.0160 (9)	0.0136 (8)	0.0043 (9)
N1	0.0432 (6)	0.0403 (6)	0.0433 (6)	−0.0021 (5)	0.0033 (5)	−0.0012 (5)
N2	0.0827 (12)	0.0817 (12)	0.1097 (14)	−0.0295 (10)	0.0162 (10)	0.0052 (10)
O1	0.0637 (7)	0.0772 (8)	0.0538 (6)	−0.0109 (6)	0.0160 (5)	−0.0209 (6)

Geometric parameters (Å, º) top

C1—C6	1.381 (2)	C14—C15	1.5445 (18)
C1—C2	1.385 (2)	C14—H14	0.9800
C1—H1	0.9300	C15—C16	1.5384 (18)
C2—C3	1.373 (2)	C15—H15	0.9800
C2—H2	0.9300	C16—C17	1.5147 (19)
C3—C4	1.360 (3)	C16—C18	1.5380 (18)
C3—H3	0.9300	C16—H16	0.9800
C4—C5	1.378 (2)	C17—O1	1.2243 (17)
C4—H4	0.9300	C17—N1	1.3438 (18)
C5—C6	1.385 (2)	C18—C19	1.516 (2)
C5—H5	0.9300	C18—C25	1.527 (2)
C6—C7	1.509 (2)	C18—H18	0.9800
C7—N1	1.4539 (17)	C19—C24	1.390 (2)
C7—H7A	0.9700	C19—C20	1.401 (2)
C7—H7B	0.9700	C20—C21	1.392 (2)
C8—N1	1.4642 (17)	C21—C22	1.381 (3)
C8—C9	1.527 (2)	C21—H21	0.9300
C8—C15	1.5526 (18)	C22—C23	1.363 (3)
C8—H8	0.9800	C22—H22	0.9300
C9—C10	1.526 (2)	C23—C24	1.391 (3)
C9—H9A	0.9700	C23—H23	0.9300
C9—H9B	0.9700	C24—H24	0.9300
C10—C11	1.530 (2)	C25—C26	1.380 (2)
C10—H10A	0.9700	C25—C30	1.386 (2)
C10—H10B	0.9700	C26—C27	1.381 (2)
C11—C12	1.528 (3)	C26—H26	0.9300
C11—H11A	0.9700	C27—C28	1.382 (2)
C11—H11B	0.9700	C27—H27	0.9300
C12—C13	1.530 (2)	C28—C29	1.372 (2)
C12—H12A	0.9700	C28—C31	1.435 (2)
C12—H12B	0.9700	C29—C30	1.378 (2)
C13—C14	1.529 (2)	C29—H29	0.9300
C13—H13A	0.9700	C30—H30	0.9300
C13—H13B	0.9700	C31—N2	1.145 (2)
C14—C20	1.517 (2)

C6—C1—C2	120.80 (15)	C13—C14—H14	106.9
C6—C1—H1	119.6	C15—C14—H14	106.9
C2—C1—H1	119.6	C16—C15—C14	113.81 (11)
C3—C2—C1	119.92 (17)	C16—C15—C8	106.19 (10)
C3—C2—H2	120.0	C14—C15—C8	112.22 (10)
C1—C2—H2	120.0	C16—C15—H15	108.1
C4—C3—C2	119.90 (16)	C14—C15—H15	108.1
C4—C3—H3	120.1	C8—C15—H15	108.1
C2—C3—H3	120.1	C17—C16—C18	109.72 (11)
C3—C4—C5	120.45 (16)	C17—C16—C15	105.24 (11)
C3—C4—H4	119.8	C18—C16—C15	115.71 (11)
C5—C4—H4	119.8	C17—C16—H16	108.6
C4—C5—C6	120.82 (16)	C18—C16—H16	108.6
C4—C5—H5	119.6	C15—C16—H16	108.6
C6—C5—H5	119.6	O1—C17—N1	125.56 (14)
C1—C6—C5	118.10 (14)	O1—C17—C16	124.95 (13)
C1—C6—C7	123.63 (13)	N1—C17—C16	109.47 (12)
C5—C6—C7	118.26 (13)	C19—C18—C25	112.51 (11)
N1—C7—C6	114.93 (11)	C19—C18—C16	108.83 (11)
N1—C7—H7A	108.5	C25—C18—C16	114.81 (11)
C6—C7—H7A	108.5	C19—C18—H18	106.7
N1—C7—H7B	108.5	C25—C18—H18	106.7
C6—C7—H7B	108.5	C16—C18—H18	106.7
H7A—C7—H7B	107.5	C24—C19—C20	120.18 (15)
N1—C8—C9	111.91 (11)	C24—C19—C18	121.17 (16)
N1—C8—C15	103.97 (10)	C20—C19—C18	118.61 (12)
C9—C8—C15	113.44 (12)	C21—C20—C19	118.50 (16)
N1—C8—H8	109.1	C21—C20—C14	123.84 (16)
C9—C8—H8	109.1	C19—C20—C14	117.64 (12)
C15—C8—H8	109.1	C22—C21—C20	120.7 (2)
C8—C9—C10	115.35 (13)	C22—C21—H21	119.6
C8—C9—H9A	108.4	C20—C21—H21	119.6
C10—C9—H9A	108.4	C23—C22—C21	120.58 (18)
C8—C9—H9B	108.4	C23—C22—H22	119.7
C10—C9—H9B	108.4	C21—C22—H22	119.7
H9A—C9—H9B	107.5	C22—C23—C24	120.17 (19)
C9—C10—C11	116.56 (14)	C22—C23—H23	119.9
C9—C10—H10A	108.2	C24—C23—H23	119.9
C11—C10—H10A	108.2	C23—C24—C19	119.8 (2)
C9—C10—H10B	108.2	C23—C24—H24	120.1
C11—C10—H10B	108.2	C19—C24—H24	120.1
H10A—C10—H10B	107.3	C26—C25—C30	117.17 (14)
C12—C11—C10	116.98 (15)	C26—C25—C18	123.84 (12)
C12—C11—H11A	108.1	C30—C25—C18	118.93 (13)
C10—C11—H11A	108.1	C25—C26—C27	121.84 (14)
C12—C11—H11B	108.1	C25—C26—H26	119.1
C10—C11—H11B	108.1	C27—C26—H26	119.1
H11A—C11—H11B	107.3	C28—C27—C26	119.86 (16)
C13—C12—C11	119.60 (14)	C28—C27—H27	120.1
C13—C12—H12A	107.4	C26—C27—H27	120.1
C11—C12—H12A	107.4	C29—C28—C27	119.17 (15)
C13—C12—H12B	107.4	C29—C28—C31	120.80 (15)
C11—C12—H12B	107.4	C27—C28—C31	120.02 (16)
H12A—C12—H12B	107.0	C28—C29—C30	120.38 (15)
C12—C13—C14	117.47 (13)	C28—C29—H29	119.8
C12—C13—H13A	107.9	C30—C29—H29	119.8
C14—C13—H13A	107.9	C29—C30—C25	121.58 (16)
C12—C13—H13B	107.9	C29—C30—H30	119.2
C14—C13—H13B	107.9	C25—C30—H30	119.2
H13A—C13—H13B	107.2	N2—C31—C28	178.3 (2)
C20—C14—C13	114.09 (12)	C17—N1—C7	121.37 (12)
C20—C14—C15	108.81 (11)	C17—N1—C8	115.06 (11)
C13—C14—C15	112.75 (12)	C7—N1—C8	123.02 (11)
C20—C14—H14	106.9

C6—C1—C2—C3	−1.1 (3)	C16—C18—C19—C20	46.38 (17)
C1—C2—C3—C4	0.4 (3)	C24—C19—C20—C21	−1.0 (2)
C2—C3—C4—C5	0.5 (3)	C18—C19—C20—C21	−178.74 (13)
C3—C4—C5—C6	−0.7 (3)	C24—C19—C20—C14	176.99 (13)
C2—C1—C6—C5	0.8 (2)	C18—C19—C20—C14	−0.76 (19)
C2—C1—C6—C7	179.66 (16)	C13—C14—C20—C21	3.8 (2)
C4—C5—C6—C1	0.1 (2)	C15—C14—C20—C21	130.65 (14)
C4—C5—C6—C7	−178.82 (15)	C13—C14—C20—C19	−174.06 (12)
C1—C6—C7—N1	15.7 (2)	C15—C14—C20—C19	−47.21 (16)
C5—C6—C7—N1	−165.47 (13)	C19—C20—C21—C22	0.2 (2)
N1—C8—C9—C10	−173.41 (12)	C14—C20—C21—C22	−177.63 (15)
C15—C8—C9—C10	69.34 (16)	C20—C21—C22—C23	0.2 (3)
C8—C9—C10—C11	−68.4 (2)	C21—C22—C23—C24	0.2 (3)
C9—C10—C11—C12	96.45 (19)	C22—C23—C24—C19	−1.0 (3)
C10—C11—C12—C13	−34.8 (2)	C20—C19—C24—C23	1.4 (2)
C11—C12—C13—C14	−70.43 (19)	C18—C19—C24—C23	179.09 (15)
C12—C13—C14—C20	−178.28 (13)	C19—C18—C25—C26	130.18 (15)
C12—C13—C14—C15	56.94 (17)	C16—C18—C25—C26	5.0 (2)
C20—C14—C15—C16	47.53 (15)	C19—C18—C25—C30	−52.81 (18)
C13—C14—C15—C16	175.15 (11)	C16—C18—C25—C30	−178.00 (13)
C20—C14—C15—C8	−73.10 (14)	C30—C25—C26—C27	−0.2 (2)
C13—C14—C15—C8	54.52 (15)	C18—C25—C26—C27	176.86 (15)
N1—C8—C15—C16	1.84 (12)	C25—C26—C27—C28	0.6 (3)
C9—C8—C15—C16	123.64 (12)	C26—C27—C28—C29	−0.6 (3)
N1—C8—C15—C14	126.78 (11)	C26—C27—C28—C31	177.93 (16)
C9—C8—C15—C14	−111.42 (13)	C27—C28—C29—C30	0.1 (3)
C14—C15—C16—C17	−124.53 (11)	C31—C28—C29—C30	−178.38 (17)
C8—C15—C16—C17	−0.57 (13)	C28—C29—C30—C25	0.3 (3)
C14—C15—C16—C18	−3.23 (16)	C26—C25—C30—C29	−0.3 (3)
C8—C15—C16—C18	120.72 (12)	C18—C25—C30—C29	−177.49 (16)
C18—C16—C17—O1	55.37 (17)	O1—C17—N1—C7	−7.3 (2)
C15—C16—C17—O1	−179.50 (13)	C16—C17—N1—C7	174.23 (11)
C18—C16—C17—N1	−126.19 (12)	O1—C17—N1—C8	−179.09 (13)
C15—C16—C17—N1	−1.06 (14)	C16—C17—N1—C8	2.48 (15)
C17—C16—C18—C19	76.27 (14)	C6—C7—N1—C17	−96.92 (16)
C15—C16—C18—C19	−42.59 (15)	C6—C7—N1—C8	74.16 (17)
C17—C16—C18—C25	−156.63 (11)	C9—C8—N1—C17	−125.55 (13)
C15—C16—C18—C25	84.51 (14)	C15—C8—N1—C17	−2.75 (14)
C25—C18—C19—C24	100.26 (16)	C9—C8—N1—C7	62.85 (16)
C16—C18—C19—C24	−131.34 (14)	C15—C8—N1—C7	−174.34 (11)
C25—C18—C19—C20	−82.02 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29···O1ⁱ	0.93	2.58	3.301 (2)	134

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₁H₃₀N₂O
M_r	446.57
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	291
a, b, c (Å)	10.0270 (11), 11.2196 (13), 21.445 (2)
β (°)	102.912 (1)
V (Å³)	2351.5 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.981, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	19941, 5413, 4118
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.128, 1.04
No. of reflections	5413
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C29—H29···O1ⁱ	0.93	2.58	3.301 (2)	134

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

We thank the National Science Foundation of China (project Nos. 21272005 and 21072003) for financial support of this work.

References

Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hu, Y.-M., Lin, X.-G., Zhu, T., Wan, J., Sun, Y.-J., Zhao, Q. S. & Yu, T. (2010). Synthesis, 42, 3467–3473. Web of Science CrossRef Google Scholar
Hu, Y.-M., Ouyang, Y., Qu, Y., Hu, Q. & Yao, H. (2009). Chem. Commun. pp. 4575–4577. Web of Science CSD CrossRef Google Scholar
Rixson, J.-E., Chaloner, T., Heath, C. H., Tietze, L. F. & Stewart, S. G. (2012). Eur. J. Org. Chem. pp. 544–558. Web of Science CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H. & Hu, Y. (2011). Acta Cryst. E67, o919. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yu, T. & Hu, Y. (2012). Acta Cryst. E68, o1184. CSD CrossRef IUCr Journals Google Scholar
Zhao, Q.-S., Hu, Q., Wen, L., Wu, M. & Hu, Y.-M. (2012). Adv. Synth. Catal. 354, 2113–2116. Web of Science CSD CrossRef CAS Google Scholar

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