6,7,15,16-Tetra-hydro-5,14-dibutyl-benzo[1,2-c:4,5-c']diacridine.

The unit cell of the title compound, C(36)H(36)N(2), contains two independent mol-ecules which are located about inversion centers. In each molecule the quinoline rings are almost planar, with mean deviations of 0.0302 (1) and 0.0173 (1) Å. In the crystal, mol-ecules are linked by C-H⋯π inter-actions into a three-dimensional network.

Related literature

For background to the applications of the title compound, an important organic synthesis inter­mediate, see: Kolosov et al. (2002 ▶); Antoniadis et al. (1994 ▶); Tonzola et al. (2003 ▶). For the synthesis of the title compound, see: Crivello & Lam 1976 ▶). Scheme faint, resolution poor

Experimental

Crystal data

C36H36N2

M = 496.67

Triclinic,

a = 9.6010 (19) Å

b = 10.386 (2) Å

c = 14.625 (3) Å

α = 77.44 (3)°

β = 78.43 (3)°

γ = 73.92 (3)°

V = 1352.4 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.979, T max = 0.993

5301 measured reflections

4978 independent reflections

2825 reflections with I > 2σ(I)

R int = 0.046

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.147

S = 1.01

4978 reflections

344 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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/S1600536812025962/go2057sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025962/go2057Isup2.hkl

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

C36H36N2	Z = 2
Mr = 496.67	F(000) = 532
Triclinic, P1	Dx = 1.220 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6010 (19) Å	Cell parameters from 25 reflections
b = 10.386 (2) Å	θ = 9–13°
c = 14.625 (3) Å	µ = 0.07 mm−1
α = 77.44 (3)°	T = 293 K
β = 78.43 (3)°	Block, colourless
γ = 73.92 (3)°	0.30 × 0.20 × 0.10 mm
V = 1352.4 (5) Å3

Enraf–Nonius CAD-4 diffractometer	2825 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.4°, θmin = 1.4°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→12
Tmin = 0.979, Tmax = 0.993	l = −17→17
5301 measured reflections	3 standard reflections every 200 reflections
4978 independent reflections	intensity decay: 1%

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)] = 0.058	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0519P)2 + 0.2931P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
4978 reflections	Δρmax = 0.17 e Å−3
344 parameters	Δρmin = −0.18 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0129 (14)

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	0.2438 (2)	−0.0834 (2)	0.71474 (14)	0.0489 (5)
C1	0.1692 (3)	−0.1557 (3)	0.78803 (17)	0.0484 (6)
C2	0.0806 (3)	−0.0862 (3)	0.86002 (19)	0.0602 (8)
H2	0.0721	0.0064	0.8549	0.072*
C3	0.0073 (3)	−0.1526 (3)	0.9370 (2)	0.0677 (8)
H3	−0.0506	−0.1055	0.9841	0.081*
C4	0.0192 (3)	−0.2912 (3)	0.9450 (2)	0.0706 (9)
H4	−0.0291	−0.3368	0.9984	0.085*
C5	0.1004 (3)	−0.3604 (3)	0.8759 (2)	0.0643 (8)
H5	0.1044	−0.4523	0.8818	0.077*
C6	0.1794 (3)	−0.2955 (3)	0.79478 (18)	0.0501 (7)
C7	0.2692 (3)	−0.3633 (3)	0.72059 (19)	0.0513 (7)
C8	0.3490 (3)	−0.2911 (3)	0.64949 (18)	0.0492 (7)
C9	0.3325 (3)	−0.1503 (3)	0.64924 (17)	0.0463 (6)
C10	0.2797 (3)	−0.5116 (3)	0.7225 (2)	0.0587 (7)
H10A	0.2959	−0.5280	0.6580	0.070*
H10B	0.1873	−0.5323	0.7536	0.070*
C11	0.4033 (3)	−0.6070 (3)	0.7741 (2)	0.0696 (9)
H11A	0.4951	−0.5835	0.7451	0.084*
H11B	0.3846	−0.5940	0.8396	0.084*
C12	0.4181 (4)	−0.7567 (3)	0.7716 (2)	0.0849 (10)
H12A	0.4283	−0.7682	0.7063	0.102*
H12B	0.5064	−0.8111	0.7965	0.102*
C13	0.2909 (4)	−0.8070 (4)	0.8270 (3)	0.1278 (16)
H13A	0.3046	−0.9005	0.8221	0.192*
H13B	0.2030	−0.7536	0.8027	0.192*
H13C	0.2826	−0.7995	0.8923	0.192*
C14	0.4177 (3)	−0.0722 (3)	0.57196 (16)	0.0453 (6)
C15	0.3755 (3)	0.0684 (3)	0.55122 (17)	0.0478 (6)
H15	0.2913	0.1144	0.5857	0.057*
C16	0.4559 (3)	0.1419 (2)	0.48028 (17)	0.0470 (6)
C17	0.4119 (3)	0.2944 (3)	0.45672 (19)	0.0560 (7)
H17A	0.3495	0.3306	0.5108	0.067*
H17B	0.3566	0.3216	0.4041	0.067*
C18	0.4536 (3)	−0.3526 (3)	0.56941 (19)	0.0582 (7)
H18A	0.4042	−0.3339	0.5145	0.070*
H18B	0.4838	−0.4505	0.5884	0.070*
N2	0.0362 (2)	0.3476 (2)	0.39887 (14)	0.0527 (6)
C19	0.0721 (3)	0.4580 (3)	0.33770 (18)	0.0516 (7)
C20	0.0175 (3)	0.5861 (3)	0.3663 (2)	0.0633 (8)
H20	−0.0381	0.5922	0.4258	0.076*
C21	0.0446 (3)	0.7013 (3)	0.3081 (2)	0.0721 (9)
H21	0.0071	0.7853	0.3276	0.087*
C22	0.1296 (3)	0.6918 (3)	0.2190 (2)	0.0778 (9)
H22	0.1477	0.7702	0.1790	0.093*
C23	0.1860 (3)	0.5692 (3)	0.1901 (2)	0.0698 (9)
H23	0.2428	0.5653	0.1308	0.084*
C24	0.1601 (3)	0.4472 (3)	0.24841 (18)	0.0540 (7)
C25	0.2160 (3)	0.3153 (3)	0.22227 (17)	0.0514 (7)
C26	0.1829 (3)	0.2053 (3)	0.28583 (17)	0.0484 (6)
C27	0.0882 (3)	0.2267 (3)	0.37299 (17)	0.0462 (6)
C28	0.0434 (3)	0.1101 (3)	0.43810 (17)	0.0474 (6)
C29	−0.0784 (3)	0.1306 (3)	0.50862 (18)	0.0504 (7)
H29	−0.1315	0.2189	0.5142	0.060*
C30	−0.1223 (3)	0.0226 (3)	0.57047 (17)	0.0484 (7)
C31	−0.2556 (3)	0.0434 (3)	0.64468 (18)	0.0549 (7)
H31A	−0.3394	0.0372	0.6197	0.066*
H31B	−0.2758	0.1338	0.6599	0.066*
C32	0.3110 (3)	0.3004 (3)	0.12746 (17)	0.0576 (7)
H32A	0.2735	0.3769	0.0802	0.069*
H32B	0.3054	0.2181	0.1088	0.069*
C33	0.4715 (3)	0.2940 (3)	0.12995 (18)	0.0614 (8)
H33A	0.4761	0.3742	0.1519	0.074*
H33B	0.5099	0.2150	0.1752	0.074*
C34	0.5678 (3)	0.2860 (3)	0.03419 (19)	0.0687 (9)
H34A	0.5232	0.3593	−0.0126	0.082*
H34B	0.6624	0.2995	0.0380	0.082*
C35	0.5909 (4)	0.1531 (4)	0.0016 (3)	0.1012 (12)
H35A	0.6519	0.1544	−0.0591	0.152*
H35B	0.4979	0.1398	−0.0036	0.152*
H35C	0.6375	0.0802	0.0466	0.152*
C36	0.2353 (3)	0.0614 (3)	0.26561 (18)	0.0593 (7)
H36A	0.3278	0.0524	0.2231	0.071*
H36B	0.1647	0.0436	0.2340	0.071*

	U11	U22	U33	U12	U13	U23
N1	0.0501 (13)	0.0521 (13)	0.0426 (12)	−0.0117 (11)	−0.0038 (11)	−0.0076 (10)
C1	0.0457 (15)	0.0557 (17)	0.0456 (15)	−0.0160 (13)	−0.0072 (13)	−0.0074 (13)
C2	0.0566 (18)	0.070 (2)	0.0517 (17)	−0.0150 (15)	−0.0016 (15)	−0.0124 (15)
C3	0.0606 (19)	0.086 (2)	0.0555 (19)	−0.0249 (17)	0.0058 (15)	−0.0136 (16)
C4	0.065 (2)	0.092 (3)	0.0564 (19)	−0.0374 (18)	0.0008 (16)	−0.0008 (17)
C5	0.0598 (18)	0.073 (2)	0.0630 (19)	−0.0289 (16)	−0.0078 (16)	−0.0025 (16)
C6	0.0418 (15)	0.0609 (18)	0.0508 (16)	−0.0178 (13)	−0.0134 (13)	−0.0032 (14)
C7	0.0474 (16)	0.0526 (17)	0.0568 (17)	−0.0140 (13)	−0.0164 (14)	−0.0049 (13)
C8	0.0522 (16)	0.0496 (17)	0.0484 (15)	−0.0128 (13)	−0.0114 (13)	−0.0097 (13)
C9	0.0475 (15)	0.0490 (16)	0.0416 (15)	−0.0081 (12)	−0.0097 (13)	−0.0079 (12)
C10	0.0562 (17)	0.0561 (18)	0.0684 (19)	−0.0200 (14)	−0.0146 (15)	−0.0077 (14)
C11	0.0596 (19)	0.065 (2)	0.082 (2)	−0.0155 (16)	−0.0184 (17)	−0.0023 (16)
C12	0.089 (3)	0.064 (2)	0.088 (2)	0.0050 (19)	−0.014 (2)	−0.0139 (18)
C13	0.112 (3)	0.079 (3)	0.188 (5)	−0.042 (2)	−0.032 (3)	0.019 (3)
C14	0.0476 (15)	0.0481 (16)	0.0382 (14)	−0.0074 (12)	−0.0065 (12)	−0.0082 (12)
C15	0.0446 (15)	0.0498 (17)	0.0446 (15)	−0.0033 (12)	−0.0035 (12)	−0.0124 (12)
C16	0.0498 (16)	0.0461 (16)	0.0424 (15)	−0.0069 (13)	−0.0067 (13)	−0.0085 (12)
C17	0.0567 (17)	0.0493 (17)	0.0553 (17)	−0.0038 (13)	−0.0042 (14)	−0.0108 (13)
C18	0.0668 (19)	0.0489 (17)	0.0585 (17)	−0.0105 (14)	−0.0090 (15)	−0.0132 (13)
N2	0.0486 (13)	0.0589 (15)	0.0485 (13)	−0.0124 (11)	−0.0039 (11)	−0.0091 (12)
C19	0.0442 (15)	0.0585 (18)	0.0492 (16)	−0.0112 (13)	−0.0075 (13)	−0.0046 (14)
C20	0.0628 (19)	0.067 (2)	0.0569 (18)	−0.0148 (16)	−0.0050 (15)	−0.0095 (16)
C21	0.075 (2)	0.062 (2)	0.075 (2)	−0.0171 (16)	−0.0064 (18)	−0.0061 (17)
C22	0.074 (2)	0.065 (2)	0.081 (2)	−0.0166 (18)	−0.0017 (19)	0.0054 (18)
C23	0.0600 (19)	0.077 (2)	0.0582 (19)	−0.0126 (17)	0.0006 (15)	0.0039 (17)
C24	0.0426 (15)	0.068 (2)	0.0486 (16)	−0.0159 (14)	−0.0062 (13)	−0.0008 (14)
C25	0.0377 (15)	0.070 (2)	0.0446 (15)	−0.0127 (13)	−0.0071 (12)	−0.0056 (14)
C26	0.0424 (15)	0.0599 (18)	0.0438 (15)	−0.0132 (13)	−0.0066 (12)	−0.0095 (13)
C27	0.0374 (14)	0.0602 (18)	0.0417 (15)	−0.0123 (13)	−0.0043 (12)	−0.0109 (13)
C28	0.0380 (14)	0.0615 (18)	0.0430 (15)	−0.0135 (13)	−0.0029 (12)	−0.0107 (13)
C29	0.0417 (15)	0.0557 (17)	0.0513 (16)	−0.0086 (12)	−0.0031 (13)	−0.0118 (13)
C30	0.0371 (14)	0.0607 (18)	0.0459 (15)	−0.0109 (13)	0.0005 (12)	−0.0139 (13)
C31	0.0429 (15)	0.0649 (18)	0.0529 (16)	−0.0107 (13)	0.0026 (13)	−0.0135 (14)
C32	0.0470 (16)	0.080 (2)	0.0444 (16)	−0.0184 (14)	−0.0050 (13)	−0.0061 (14)
C33	0.0485 (17)	0.084 (2)	0.0507 (17)	−0.0206 (15)	−0.0019 (14)	−0.0096 (15)
C34	0.0504 (17)	0.098 (3)	0.0561 (18)	−0.0258 (17)	0.0003 (15)	−0.0065 (17)
C35	0.088 (3)	0.117 (3)	0.094 (3)	−0.018 (2)	0.010 (2)	−0.042 (2)
C36	0.0523 (17)	0.078 (2)	0.0473 (16)	−0.0182 (15)	0.0034 (13)	−0.0170 (15)

N1—C9	1.327 (3)	N2—C27	1.324 (3)
N1—C1	1.366 (3)	N2—C19	1.373 (3)
C1—C2	1.409 (3)	C19—C20	1.409 (4)
C1—C6	1.410 (3)	C19—C24	1.414 (3)
C2—C3	1.360 (4)	C20—C21	1.366 (4)
C2—H2	0.9300	C20—H20	0.9300
C3—C4	1.393 (4)	C21—C22	1.399 (4)
C3—H3	0.9300	C21—H21	0.9300
C4—C5	1.355 (4)	C22—C23	1.362 (4)
C4—H4	0.9300	C22—H22	0.9300
C5—C6	1.419 (4)	C23—C24	1.419 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.427 (4)	C24—C25	1.431 (4)
C7—C8	1.375 (3)	C25—C26	1.376 (3)
C7—C10	1.509 (3)	C25—C32	1.512 (3)
C8—C9	1.426 (3)	C26—C27	1.431 (3)
C8—C18	1.512 (3)	C26—C36	1.513 (4)
C9—C14	1.484 (3)	C27—C28	1.476 (3)
C10—C11	1.530 (4)	C28—C30ii	1.396 (3)
C10—H10A	0.9700	C28—C29	1.397 (3)
C10—H10B	0.9700	C29—C30	1.386 (3)
C11—C12	1.529 (4)	C29—H29	0.9300
C11—H11A	0.9700	C30—C28ii	1.396 (3)
C11—H11B	0.9700	C30—C31	1.502 (3)
C12—C13	1.481 (4)	C31—C36ii	1.519 (4)
C12—H12A	0.9700	C31—H31A	0.9700
C12—H12B	0.9700	C31—H31B	0.9700
C13—H13A	0.9600	C32—C33	1.531 (3)
C13—H13B	0.9600	C32—H32A	0.9700
C13—H13C	0.9600	C32—H32B	0.9700
C14—C15	1.384 (3)	C33—C34	1.521 (3)
C14—C16i	1.401 (3)	C33—H33A	0.9700
C15—C16	1.384 (3)	C33—H33B	0.9700
C15—H15	0.9300	C34—C35	1.502 (4)
C16—C14i	1.401 (3)	C34—H34A	0.9700
C16—C17	1.502 (3)	C34—H34B	0.9700
C17—C18i	1.520 (3)	C35—H35A	0.9600
C17—H17A	0.9700	C35—H35B	0.9600
C17—H17B	0.9700	C35—H35C	0.9600
C18—C17i	1.520 (3)	C36—C31ii	1.519 (4)
C18—H18A	0.9700	C36—H36A	0.9700
C18—H18B	0.9700	C36—H36B	0.9700
C9—N1—C1	117.5 (2)	C27—N2—C19	118.1 (2)
N1—C1—C2	117.6 (2)	N2—C19—C20	117.7 (2)
N1—C1—C6	122.9 (2)	N2—C19—C24	122.5 (2)
C2—C1—C6	119.5 (2)	C20—C19—C24	119.8 (3)
C3—C2—C1	120.9 (3)	C21—C20—C19	121.1 (3)
C3—C2—H2	119.5	C21—C20—H20	119.4
C1—C2—H2	119.5	C19—C20—H20	119.4
C2—C3—C4	119.8 (3)	C20—C21—C22	119.4 (3)
C2—C3—H3	120.1	C20—C21—H21	120.3
C4—C3—H3	120.1	C22—C21—H21	120.3
C5—C4—C3	120.7 (3)	C23—C22—C21	120.8 (3)
C5—C4—H4	119.6	C23—C22—H22	119.6
C3—C4—H4	119.6	C21—C22—H22	119.6
C4—C5—C6	121.3 (3)	C22—C23—C24	121.5 (3)
C4—C5—H5	119.4	C22—C23—H23	119.2
C6—C5—H5	119.4	C24—C23—H23	119.2
C1—C6—C5	117.6 (3)	C19—C24—C23	117.3 (3)
C1—C6—C7	118.4 (2)	C19—C24—C25	118.4 (2)
C5—C6—C7	124.0 (3)	C23—C24—C25	124.3 (3)
C8—C7—C6	118.2 (2)	C26—C25—C24	118.3 (2)
C8—C7—C10	121.2 (2)	C26—C25—C32	122.1 (3)
C6—C7—C10	120.6 (2)	C24—C25—C32	119.6 (2)
C7—C8—C9	119.2 (2)	C25—C26—C27	119.4 (2)
C7—C8—C18	123.5 (2)	C25—C26—C36	122.9 (2)
C9—C8—C18	117.3 (2)	C27—C26—C36	117.7 (2)
N1—C9—C8	123.6 (2)	N2—C27—C26	123.2 (2)
N1—C9—C14	117.2 (2)	N2—C27—C28	117.2 (2)
C8—C9—C14	119.2 (2)	C26—C27—C28	119.5 (2)
C7—C10—C11	112.8 (2)	C30ii—C28—C29	119.0 (2)
C7—C10—H10A	109.0	C30ii—C28—C27	120.2 (2)
C11—C10—H10A	109.0	C29—C28—C27	120.8 (2)
C7—C10—H10B	109.0	C30—C29—C28	121.7 (2)
C11—C10—H10B	109.0	C30—C29—H29	119.1
H10A—C10—H10B	107.8	C28—C29—H29	119.1
C12—C11—C10	112.5 (2)	C29—C30—C28ii	119.3 (2)
C12—C11—H11A	109.1	C29—C30—C31	122.1 (2)
C10—C11—H11A	109.1	C28ii—C30—C31	118.6 (2)
C12—C11—H11B	109.1	C30—C31—C36ii	111.8 (2)
C10—C11—H11B	109.1	C30—C31—H31A	109.3
H11A—C11—H11B	107.8	C36ii—C31—H31A	109.3
C13—C12—C11	112.8 (3)	C30—C31—H31B	109.3
C13—C12—H12A	109.0	C36ii—C31—H31B	109.3
C11—C12—H12A	109.0	H31A—C31—H31B	107.9
C13—C12—H12B	109.0	C25—C32—C33	112.3 (2)
C11—C12—H12B	109.0	C25—C32—H32A	109.1
H12A—C12—H12B	107.8	C33—C32—H32A	109.1
C12—C13—H13A	109.5	C25—C32—H32B	109.1
C12—C13—H13B	109.5	C33—C32—H32B	109.1
H13A—C13—H13B	109.5	H32A—C32—H32B	107.9
C12—C13—H13C	109.5	C34—C33—C32	113.3 (2)
H13A—C13—H13C	109.5	C34—C33—H33A	108.9
H13B—C13—H13C	109.5	C32—C33—H33A	108.9
C15—C14—C16i	119.4 (2)	C34—C33—H33B	108.9
C15—C14—C9	121.3 (2)	C32—C33—H33B	108.9
C16i—C14—C9	119.4 (2)	H33A—C33—H33B	107.7
C16—C15—C14	121.5 (2)	C35—C34—C33	113.4 (3)
C16—C15—H15	119.2	C35—C34—H34A	108.9
C14—C15—H15	119.2	C33—C34—H34A	108.9
C15—C16—C14i	119.1 (2)	C35—C34—H34B	108.9
C15—C16—C17	122.3 (2)	C33—C34—H34B	108.9
C14i—C16—C17	118.6 (2)	H34A—C34—H34B	107.7
C16—C17—C18i	110.7 (2)	C34—C35—H35A	109.5
C16—C17—H17A	109.5	C34—C35—H35B	109.5
C18i—C17—H17A	109.5	H35A—C35—H35B	109.5
C16—C17—H17B	109.5	C34—C35—H35C	109.5
C18i—C17—H17B	109.5	H35A—C35—H35C	109.5
H17A—C17—H17B	108.1	H35B—C35—H35C	109.5
C8—C18—C17i	110.8 (2)	C26—C36—C31ii	112.2 (2)
C8—C18—H18A	109.5	C26—C36—H36A	109.2
C17i—C18—H18A	109.5	C31ii—C36—H36A	109.2
C8—C18—H18B	109.5	C26—C36—H36B	109.2
C17i—C18—H18B	109.5	C31ii—C36—H36B	109.2
H18A—C18—H18B	108.1	H36A—C36—H36B	107.9
C9—N1—C1—C2	176.9 (2)	C27—N2—C19—C20	−179.4 (2)
C9—N1—C1—C6	−2.1 (3)	C27—N2—C19—C24	0.9 (4)
N1—C1—C2—C3	−177.6 (2)	N2—C19—C20—C21	−178.0 (3)
C6—C1—C2—C3	1.5 (4)	C24—C19—C20—C21	1.8 (4)
C1—C2—C3—C4	−0.2 (4)	C19—C20—C21—C22	−0.7 (4)
C2—C3—C4—C5	−1.6 (5)	C20—C21—C22—C23	−0.5 (5)
C3—C4—C5—C6	2.0 (4)	C21—C22—C23—C24	0.5 (5)
N1—C1—C6—C5	177.9 (2)	N2—C19—C24—C23	178.1 (2)
C2—C1—C6—C5	−1.0 (4)	C20—C19—C24—C23	−1.6 (4)
N1—C1—C6—C7	−1.4 (4)	N2—C19—C24—C25	−1.4 (4)
C2—C1—C6—C7	179.6 (2)	C20—C19—C24—C25	178.9 (2)
C4—C5—C6—C1	−0.7 (4)	C22—C23—C24—C19	0.5 (4)
C4—C5—C6—C7	178.6 (3)	C22—C23—C24—C25	179.9 (3)
C1—C6—C7—C8	4.3 (3)	C19—C24—C25—C26	−0.8 (4)
C5—C6—C7—C8	−175.0 (2)	C23—C24—C25—C26	179.7 (2)
C1—C6—C7—C10	−177.8 (2)	C19—C24—C25—C32	−179.7 (2)
C5—C6—C7—C10	2.9 (4)	C23—C24—C25—C32	0.9 (4)
C6—C7—C8—C9	−3.8 (4)	C24—C25—C26—C27	3.3 (3)
C10—C7—C8—C9	178.3 (2)	C32—C25—C26—C27	−177.8 (2)
C6—C7—C8—C18	177.0 (2)	C24—C25—C26—C36	179.7 (2)
C10—C7—C8—C18	−0.8 (4)	C32—C25—C26—C36	−1.5 (4)
C1—N1—C9—C8	2.7 (4)	C19—N2—C27—C26	1.8 (4)
C1—N1—C9—C14	−177.6 (2)	C19—N2—C27—C28	−177.6 (2)
C7—C8—C9—N1	0.3 (4)	C25—C26—C27—N2	−4.0 (4)
C18—C8—C9—N1	179.5 (2)	C36—C26—C27—N2	179.5 (2)
C7—C8—C9—C14	−179.4 (2)	C25—C26—C27—C28	175.4 (2)
C18—C8—C9—C14	−0.2 (3)	C36—C26—C27—C28	−1.2 (3)
C8—C7—C10—C11	88.0 (3)	N2—C27—C28—C30ii	−162.5 (2)
C6—C7—C10—C11	−89.8 (3)	C26—C27—C28—C30ii	18.1 (3)
C7—C10—C11—C12	−177.2 (3)	N2—C27—C28—C29	17.8 (3)
C10—C11—C12—C13	−67.4 (4)	C26—C27—C28—C29	−161.6 (2)
N1—C9—C14—C15	−19.7 (3)	C30ii—C28—C29—C30	0.4 (4)
C8—C9—C14—C15	160.1 (2)	C27—C28—C29—C30	−180.0 (2)
N1—C9—C14—C16i	159.6 (2)	C28—C29—C30—C28ii	−0.4 (4)
C8—C9—C14—C16i	−20.7 (3)	C28—C29—C30—C31	−178.2 (2)
C16i—C14—C15—C16	−0.3 (4)	C29—C30—C31—C36ii	−145.6 (2)
C9—C14—C15—C16	178.9 (2)	C28ii—C30—C31—C36ii	36.6 (3)
C14—C15—C16—C14i	0.3 (4)	C26—C25—C32—C33	−96.0 (3)
C14—C15—C16—C17	180.0 (2)	C24—C25—C32—C33	82.8 (3)
C15—C16—C17—C18i	143.2 (2)	C25—C32—C33—C34	−177.2 (2)
C14i—C16—C17—C18i	−37.2 (3)	C32—C33—C34—C35	−69.2 (3)
C7—C8—C18—C17i	−142.9 (3)	C25—C26—C36—C31ii	150.5 (2)
C9—C8—C18—C17i	38.0 (3)	C27—C26—C36—C31ii	−33.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···Cg23	0.97	2.79	3.688 (3)	155
C31—H31A···Cg4iii	0.97	2.70	3.630 (3)	160
C34—H34B···Cg2i	0.97	2.81	3.669 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg23, Cg4 and Cg2 are the centroids of the of ring containing N2, the ring containing C15 and the ring containing C2, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17B⋯Cg23	0.97	2.79	3.688 (3)	155
C31—H31A⋯Cg4i	0.97	2.70	3.630 (3)	160
C34—H34B⋯Cg2ii	0.97	2.81	3.669 (3)	148

Symmetry codes: (i) ; (ii) .