4-(6-Benzyl-7-oxo-1,2,3,4,5,5a,5a(1),6,7,7a,8,12b-dodeca-hydro-benzo[f]cyclo-octa-[cd]isoindol-8-yl)benzonitrile.

In the title compound, C31H30N2O, the cis-fused cyclo-hexene and cyclo-octane 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 cyclo-hexene and cyclo-octane rings. In the crystal, mol-ecules are linked into inversion dimers through pairs of weak C-H⋯O inter-actions.

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 = 446.57

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.128

S = 1.04

5413 reflections

308 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.18 e Å−3

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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006880/is5255sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006880/is5255Isup3.cml

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

C31H30N2O	F(000) = 952
Mr = 446.57	Dx = 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

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

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(Fo2) + (0.0539P)2 + 0.5346P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
5413 reflections	Δρmax = 0.23 e Å−3
308 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .