Crystal structure of (2E,3E)-N (2),N (3)-bis-(3-ethyl-[1,1'-biphen-yl]-4-yl)butane-2,3-di-imine.

In the title compound, C32H32N2, synthesized by the con-densation reaction of 2-ethyl-4-phenyl-aniline and 2,3-butane-dione, the conformation about the C=N bonds is E and the substituted biphenyl units are trans to one another. In the two biphenyl ring systems, the planes of the two rings are inclined to one another by 25.25 (19) and 28.01 (19)°. The planes of the ethyl-substituted benzene rings are inclined to one another by 20.23 (19)° and to the mean plane of the butane-2,3-di-imine unit [maximum deviation = 0.014 (4) Å] by 83.19 (19) and 63.38 (19)°. In the crystal, mol-ecules are linked by C-H⋯π inter-actions, forming sheets lying parallel to (101).

Related literature

For literature on α-di­imine palladium and nickel complex catalysts for the polymerization of α-olefins, see: Johnson et al. (1995 ▸); Gates et al. (2000 ▸). For the crystal structure of a similar compound, see: Chen et al. (2014 ▸).

Experimental

Crystal data

C32H32N2

M = 444.60

Triclinic,

a = 9.622 (4) Å

b = 9.707 (5) Å

c = 14.666 (7) Å

α = 77.288 (5)°

β = 86.934 (4)°

γ = 74.736 (4)°

V = 1289.1 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.28 × 0.26 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▸) T min = 0.982, T max = 0.984

9264 measured reflections

4719 independent reflections

2323 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.245

S = 1.03

4719 reflections

311 parameters

62 restraints

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); 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/S2056989015005071/su5091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015005071/su5091Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015005071/su5091Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015005071/su5091fig1.tif

Mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

CCDC reference: 1053619

Additional supporting information: crystallographic information; 3D view; checkCIF report

C32H32N2	Z = 2
Mr = 444.60	F(000) = 476
Triclinic, P1	Dx = 1.145 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.622 (4) Å	Cell parameters from 1713 reflections
b = 9.707 (5) Å	θ = 2.2–23.0°
c = 14.666 (7) Å	µ = 0.07 mm−1
α = 77.288 (5)°	T = 296 K
β = 86.934 (4)°	Block, yellow
γ = 74.736 (4)°	0.28 × 0.26 × 0.25 mm
V = 1289.1 (10) Å3

Bruker APEXII CCD diffractometer	4719 independent reflections
Radiation source: fine-focus sealed tube	2323 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→11
Tmin = 0.982, Tmax = 0.984	k = −11→11
9264 measured reflections	l = −17→17

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) = 0.245	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0989P)2 + 0.5812P] where P = (Fo2 + 2Fc2)/3
4719 reflections	(Δ/σ)max = 0.001
311 parameters	Δρmax = 0.42 e Å−3
62 restraints	Δρmin = −0.32 e Å−3

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
C4	0.2795 (3)	0.7460 (4)	0.3800 (2)	0.0475 (9)
C7	0.2487 (3)	0.7538 (4)	0.4796 (2)	0.0447 (8)
C24	0.8794 (4)	0.7005 (4)	−0.4998 (2)	0.0547 (9)
H24	0.9548	0.6738	−0.4571	0.066*
C23	0.7383 (3)	0.7411 (4)	−0.4689 (2)	0.0447 (8)
C20	0.7041 (4)	0.7451 (4)	−0.3690 (2)	0.0474 (9)
N1	0.3646 (4)	0.7226 (4)	0.0967 (2)	0.0691 (10)
C2	0.4010 (4)	0.6174 (4)	0.2631 (2)	0.0600 (10)
H2	0.4631	0.5342	0.2484	0.072*
N2	0.6087 (4)	0.7552 (4)	−0.08534 (19)	0.0677 (9)
C25	0.9095 (4)	0.6991 (4)	−0.5925 (2)	0.0606 (10)
H25	1.0046	0.6703	−0.6114	0.073*
C28	0.6287 (4)	0.7801 (4)	−0.5354 (2)	0.0524 (9)
H28	0.5332	0.8061	−0.5166	0.063*
C27	0.6588 (4)	0.7807 (4)	−0.6286 (2)	0.0575 (10)
H27	0.5841	0.8086	−0.6719	0.069*
C21	0.5806 (4)	0.8396 (4)	−0.3438 (2)	0.0624 (10)
H21	0.5183	0.9033	−0.3901	0.075*
C8	0.2624 (4)	0.6280 (4)	0.5489 (2)	0.0532 (9)
H8	0.2903	0.5372	0.5328	0.064*
C3	0.3721 (4)	0.6228 (4)	0.3557 (2)	0.0556 (9)
H3	0.4149	0.5432	0.4023	0.067*
C17	0.6367 (4)	0.7479 (4)	−0.1810 (2)	0.0577 (10)
C12	0.2056 (4)	0.8868 (4)	0.5063 (2)	0.0588 (10)
H12	0.1960	0.9726	0.4611	0.071*
C9	0.2352 (4)	0.6355 (5)	0.6412 (2)	0.0638 (11)
H9	0.2464	0.5499	0.6869	0.077*
C1	0.3390 (4)	0.7335 (5)	0.1921 (2)	0.0586 (10)
C15	0.4766 (4)	0.7491 (4)	0.0550 (2)	0.0616 (10)
C16	0.4957 (4)	0.7297 (4)	−0.0440 (2)	0.0602 (10)
C22	0.5486 (4)	0.8406 (5)	−0.2514 (2)	0.0705 (12)
H22	0.4653	0.9056	−0.2363	0.085*
C11	0.1765 (4)	0.8947 (5)	0.5984 (3)	0.0692 (11)
H11	0.1466	0.9853	0.6147	0.083*
C5	0.2159 (4)	0.8603 (4)	0.3076 (2)	0.0571 (10)
H5	0.1526	0.9429	0.3223	0.069*
C19	0.7939 (4)	0.6534 (4)	−0.2969 (2)	0.0576 (10)
H19	0.8780	0.5898	−0.3121	0.069*
C6	0.2429 (4)	0.8566 (5)	0.2135 (2)	0.0655 (10)
C18	0.7635 (4)	0.6525 (5)	−0.2029 (2)	0.0655 (11)
C26	0.7997 (4)	0.7401 (4)	−0.6574 (2)	0.0625 (11)
H26	0.8204	0.7404	−0.7201	0.075*
C32	0.3837 (5)	0.6771 (5)	−0.0834 (3)	0.0817 (13)
H32A	0.2988	0.7562	−0.0990	0.123*
H32B	0.3602	0.5992	−0.0379	0.123*
H32C	0.4203	0.6424	−0.1387	0.123*
C10	0.1917 (4)	0.7683 (5)	0.6659 (3)	0.0724 (12)
H10	0.1726	0.7731	0.7281	0.087*
C31	0.5890 (5)	0.7985 (6)	0.0961 (3)	0.1001 (17)
H31A	0.5484	0.8434	0.1470	0.150*
H31B	0.6226	0.8680	0.0490	0.150*
H31C	0.6682	0.7159	0.1186	0.150*
C29	0.8580 (5)	0.5493 (6)	−0.1247 (3)	0.0996 (15)
H29A	0.8701	0.6061	−0.0804	0.119*
H29B	0.8051	0.4804	−0.0930	0.119*
C13	0.1671 (5)	0.9816 (6)	0.1373 (3)	0.0957 (14)
H13A	0.1878	1.0705	0.1459	0.115*
H13B	0.2072	0.9637	0.0776	0.115*
C30	0.9944 (7)	0.4688 (9)	−0.1444 (4)	0.187 (3)
H30A	0.9911	0.4376	−0.2018	0.281*
H30B	1.0250	0.3847	−0.0945	0.281*
H30C	1.0611	0.5284	−0.1504	0.281*
C14	0.0125 (7)	1.0059 (9)	0.1331 (5)	0.199 (4)
H14A	−0.0101	0.9417	0.0981	0.298*
H14B	−0.0302	1.1055	0.1030	0.298*
H14C	−0.0248	0.9865	0.1953	0.298*

	U11	U22	U33	U12	U13	U23
C4	0.0409 (19)	0.061 (2)	0.0438 (19)	−0.0161 (17)	0.0055 (15)	−0.0145 (17)
C7	0.0345 (18)	0.056 (2)	0.0490 (19)	−0.0165 (16)	0.0058 (14)	−0.0174 (17)
C24	0.047 (2)	0.071 (3)	0.049 (2)	−0.0169 (19)	0.0011 (16)	−0.0179 (18)
C23	0.043 (2)	0.051 (2)	0.0425 (18)	−0.0159 (17)	0.0024 (15)	−0.0124 (15)
C20	0.044 (2)	0.057 (2)	0.0420 (19)	−0.0141 (17)	0.0059 (15)	−0.0122 (16)
N1	0.073 (2)	0.099 (3)	0.0452 (18)	−0.031 (2)	0.0112 (16)	−0.0270 (17)
C2	0.058 (2)	0.069 (3)	0.056 (2)	−0.012 (2)	0.0103 (18)	−0.028 (2)
N2	0.072 (2)	0.091 (3)	0.0439 (17)	−0.0216 (19)	0.0090 (16)	−0.0229 (16)
C25	0.050 (2)	0.079 (3)	0.057 (2)	−0.020 (2)	0.0148 (18)	−0.025 (2)
C28	0.046 (2)	0.063 (2)	0.050 (2)	−0.0159 (18)	0.0015 (16)	−0.0123 (17)
C27	0.059 (2)	0.069 (3)	0.046 (2)	−0.019 (2)	−0.0073 (17)	−0.0099 (17)
C21	0.058 (2)	0.072 (3)	0.046 (2)	−0.002 (2)	0.0077 (17)	−0.0098 (18)
C8	0.051 (2)	0.060 (2)	0.048 (2)	−0.0113 (18)	0.0052 (16)	−0.0161 (17)
C3	0.054 (2)	0.063 (2)	0.051 (2)	−0.0141 (19)	0.0057 (17)	−0.0186 (18)
C17	0.060 (2)	0.075 (3)	0.042 (2)	−0.019 (2)	0.0078 (17)	−0.0194 (18)
C12	0.063 (2)	0.060 (2)	0.057 (2)	−0.021 (2)	0.0075 (18)	−0.0177 (18)
C9	0.064 (3)	0.075 (3)	0.050 (2)	−0.016 (2)	−0.0011 (18)	−0.010 (2)
C1	0.058 (2)	0.080 (3)	0.047 (2)	−0.027 (2)	0.0107 (17)	−0.024 (2)
C15	0.064 (3)	0.081 (3)	0.043 (2)	−0.018 (2)	0.0062 (18)	−0.0205 (19)
C16	0.061 (2)	0.076 (3)	0.044 (2)	−0.015 (2)	0.0052 (18)	−0.0185 (18)
C22	0.065 (3)	0.082 (3)	0.053 (2)	0.001 (2)	0.0136 (19)	−0.017 (2)
C11	0.078 (3)	0.071 (3)	0.066 (3)	−0.021 (2)	0.013 (2)	−0.032 (2)
C5	0.055 (2)	0.064 (2)	0.052 (2)	−0.0144 (19)	0.0105 (17)	−0.0154 (18)
C19	0.050 (2)	0.073 (3)	0.048 (2)	−0.0078 (19)	0.0029 (16)	−0.0181 (18)
C6	0.067 (2)	0.079 (3)	0.049 (2)	−0.021 (2)	0.0078 (18)	−0.0092 (18)
C18	0.059 (2)	0.093 (3)	0.0417 (19)	−0.014 (2)	−0.0026 (16)	−0.0144 (19)
C26	0.075 (3)	0.076 (3)	0.045 (2)	−0.029 (2)	0.0101 (19)	−0.0212 (19)
C32	0.084 (3)	0.120 (4)	0.053 (2)	−0.037 (3)	0.008 (2)	−0.033 (2)
C10	0.074 (3)	0.102 (4)	0.049 (2)	−0.024 (3)	0.008 (2)	−0.032 (2)
C31	0.092 (3)	0.176 (5)	0.060 (3)	−0.065 (4)	0.016 (2)	−0.050 (3)
C29	0.085 (3)	0.142 (4)	0.053 (2)	0.001 (3)	−0.009 (2)	−0.017 (2)
C13	0.095 (3)	0.104 (3)	0.070 (3)	−0.011 (3)	0.000 (2)	0.002 (2)
C30	0.137 (5)	0.249 (7)	0.089 (4)	0.063 (5)	−0.009 (4)	0.009 (4)
C14	0.137 (5)	0.234 (7)	0.137 (5)	0.028 (6)	−0.017 (4)	0.057 (5)

C4—C5	1.388 (5)	C9—H9	0.9300
C4—C3	1.395 (5)	C1—C6	1.391 (5)
C4—C7	1.489 (4)	C15—C31	1.494 (6)
C7—C12	1.384 (5)	C15—C16	1.501 (5)
C7—C8	1.387 (5)	C16—C32	1.497 (5)
C24—C25	1.377 (4)	C22—H22	0.9300
C24—C23	1.391 (4)	C11—C10	1.377 (6)
C24—H24	0.9300	C11—H11	0.9300
C23—C28	1.394 (4)	C5—C6	1.396 (5)
C23—C20	1.491 (4)	C5—H5	0.9300
C20—C21	1.386 (5)	C19—C18	1.392 (5)
C20—C19	1.392 (5)	C19—H19	0.9300
N1—C15	1.269 (4)	C6—C13	1.510 (6)
N1—C1	1.430 (4)	C18—C29	1.506 (5)
C2—C3	1.380 (4)	C26—H26	0.9300
C2—C1	1.381 (5)	C32—H32A	0.9600
C2—H2	0.9300	C32—H32B	0.9600
N2—C16	1.272 (4)	C32—H32C	0.9600
N2—C17	1.428 (4)	C10—H10	0.9300
C25—C26	1.379 (5)	C31—H31A	0.9600
C25—H25	0.9300	C31—H31B	0.9600
C28—C27	1.380 (4)	C31—H31C	0.9600
C28—H28	0.9300	C29—C30	1.391 (6)
C27—C26	1.379 (5)	C29—H29A	0.9700
C27—H27	0.9300	C29—H29B	0.9700
C21—C22	1.375 (5)	C13—C14	1.446 (7)
C21—H21	0.9300	C13—H13A	0.9700
C8—C9	1.379 (5)	C13—H13B	0.9700
C8—H8	0.9300	C30—H30A	0.9600
C3—H3	0.9300	C30—H30B	0.9600
C17—C22	1.370 (5)	C30—H30C	0.9600
C17—C18	1.394 (5)	C14—H14A	0.9600
C12—C11	1.379 (5)	C14—H14B	0.9600
C12—H12	0.9300	C14—H14C	0.9600
C9—C10	1.369 (6)
C5—C4—C3	117.2 (3)	C21—C22—H22	119.3
C5—C4—C7	121.4 (3)	C10—C11—C12	119.8 (4)
C3—C4—C7	121.3 (3)	C10—C11—H11	120.1
C12—C7—C8	117.7 (3)	C12—C11—H11	120.1
C12—C7—C4	121.1 (3)	C4—C5—C6	122.8 (4)
C8—C7—C4	121.2 (3)	C4—C5—H5	118.6
C25—C24—C23	121.2 (3)	C6—C5—H5	118.6
C25—C24—H24	119.4	C20—C19—C18	123.0 (3)
C23—C24—H24	119.4	C20—C19—H19	118.5
C24—C23—C28	117.4 (3)	C18—C19—H19	118.5
C24—C23—C20	121.8 (3)	C1—C6—C5	118.2 (4)
C28—C23—C20	120.8 (3)	C1—C6—C13	121.0 (4)
C21—C20—C19	117.0 (3)	C5—C6—C13	120.7 (4)
C21—C20—C23	121.4 (3)	C19—C18—C17	117.9 (3)
C19—C20—C23	121.7 (3)	C19—C18—C29	122.9 (4)
C15—N1—C1	120.7 (3)	C17—C18—C29	119.1 (3)
C3—C2—C1	121.0 (4)	C25—C26—C27	119.4 (3)
C3—C2—H2	119.5	C25—C26—H26	120.3
C1—C2—H2	119.5	C27—C26—H26	120.3
C16—N2—C17	122.1 (3)	C16—C32—H32A	109.5
C24—C25—C26	120.5 (3)	C16—C32—H32B	109.5
C24—C25—H25	119.8	H32A—C32—H32B	109.5
C26—C25—H25	119.8	C16—C32—H32C	109.5
C27—C28—C23	121.4 (3)	H32A—C32—H32C	109.5
C27—C28—H28	119.3	H32B—C32—H32C	109.5
C23—C28—H28	119.3	C9—C10—C11	119.8 (4)
C26—C27—C28	120.1 (3)	C9—C10—H10	120.1
C26—C27—H27	120.0	C11—C10—H10	120.1
C28—C27—H27	120.0	C15—C31—H31A	109.5
C22—C21—C20	121.0 (4)	C15—C31—H31B	109.5
C22—C21—H21	119.5	H31A—C31—H31B	109.5
C20—C21—H21	119.5	C15—C31—H31C	109.5
C9—C8—C7	121.1 (4)	H31A—C31—H31C	109.5
C9—C8—H8	119.5	H31B—C31—H31C	109.5
C7—C8—H8	119.5	C30—C29—C18	119.9 (4)
C2—C3—C4	120.8 (3)	C30—C29—H29A	107.3
C2—C3—H3	119.6	C18—C29—H29A	107.3
C4—C3—H3	119.6	C30—C29—H29B	107.3
C22—C17—C18	119.8 (3)	C18—C29—H29B	107.3
C22—C17—N2	121.5 (3)	H29A—C29—H29B	106.9
C18—C17—N2	118.5 (3)	C14—C13—C6	115.4 (4)
C11—C12—C7	121.4 (4)	C14—C13—H13A	108.4
C11—C12—H12	119.3	C6—C13—H13A	108.4
C7—C12—H12	119.3	C14—C13—H13B	108.4
C10—C9—C8	120.3 (4)	C6—C13—H13B	108.4
C10—C9—H9	119.9	H13A—C13—H13B	107.5
C8—C9—H9	119.9	C29—C30—H30A	109.5
C2—C1—C6	119.8 (3)	C29—C30—H30B	109.5
C2—C1—N1	120.1 (4)	H30A—C30—H30B	109.5
C6—C1—N1	119.9 (4)	C29—C30—H30C	109.5
N1—C15—C31	125.4 (3)	H30A—C30—H30C	109.5
N1—C15—C16	116.5 (4)	H30B—C30—H30C	109.5
C31—C15—C16	118.1 (3)	C13—C14—H14A	109.5
N2—C16—C32	126.3 (3)	C13—C14—H14B	109.5
N2—C16—C15	116.3 (4)	H14A—C14—H14B	109.5
C32—C16—C15	117.3 (3)	C13—C14—H14C	109.5
C17—C22—C21	121.4 (4)	H14A—C14—H14C	109.5
C17—C22—H22	119.3	H14B—C14—H14C	109.5
C5—C4—C7—C12	−25.7 (5)	C17—N2—C16—C15	−176.9 (4)
C3—C4—C7—C12	155.0 (3)	N1—C15—C16—N2	−179.4 (4)
C5—C4—C7—C8	154.3 (3)	C31—C15—C16—N2	1.0 (6)
C3—C4—C7—C8	−24.9 (5)	N1—C15—C16—C32	−1.7 (6)
C25—C24—C23—C28	0.1 (5)	C31—C15—C16—C32	178.8 (4)
C25—C24—C23—C20	−179.2 (3)	C18—C17—C22—C21	1.6 (6)
C24—C23—C20—C21	151.7 (4)	N2—C17—C22—C21	175.9 (4)
C28—C23—C20—C21	−27.6 (5)	C20—C21—C22—C17	−0.5 (6)
C24—C23—C20—C19	−28.9 (5)	C7—C12—C11—C10	0.7 (6)
C28—C23—C20—C19	151.8 (3)	C3—C4—C5—C6	−1.0 (5)
C23—C24—C25—C26	0.9 (6)	C7—C4—C5—C6	179.7 (3)
C24—C23—C28—C27	−1.1 (5)	C21—C20—C19—C18	0.7 (6)
C20—C23—C28—C27	178.2 (3)	C23—C20—C19—C18	−178.7 (3)
C23—C28—C27—C26	1.1 (5)	C2—C1—C6—C5	2.1 (6)
C19—C20—C21—C22	−0.6 (6)	N1—C1—C6—C5	177.1 (3)
C23—C20—C21—C22	178.8 (3)	C2—C1—C6—C13	−176.5 (4)
C12—C7—C8—C9	−0.6 (5)	N1—C1—C6—C13	−1.5 (6)
C4—C7—C8—C9	179.3 (3)	C4—C5—C6—C1	−0.8 (6)
C1—C2—C3—C4	−0.1 (6)	C4—C5—C6—C13	177.9 (4)
C5—C4—C3—C2	1.4 (5)	C20—C19—C18—C17	0.3 (6)
C7—C4—C3—C2	−179.3 (3)	C20—C19—C18—C29	177.7 (4)
C16—N2—C17—C22	63.3 (6)	C22—C17—C18—C19	−1.4 (6)
C16—N2—C17—C18	−122.3 (4)	N2—C17—C18—C19	−175.9 (3)
C8—C7—C12—C11	−0.3 (5)	C22—C17—C18—C29	−178.9 (4)
C4—C7—C12—C11	179.8 (3)	N2—C17—C18—C29	6.6 (6)
C7—C8—C9—C10	1.0 (6)	C24—C25—C26—C27	−0.9 (6)
C3—C2—C1—C6	−1.7 (6)	C28—C27—C26—C25	0.0 (6)
C3—C2—C1—N1	−176.7 (3)	C8—C9—C10—C11	−0.6 (6)
C15—N1—C1—C2	−84.0 (5)	C12—C11—C10—C9	−0.2 (6)
C15—N1—C1—C6	100.9 (5)	C19—C18—C29—C30	12.0 (9)
C1—N1—C15—C31	−2.4 (7)	C17—C18—C29—C30	−170.6 (6)
C1—N1—C15—C16	178.0 (4)	C1—C6—C13—C14	114.5 (6)
C17—N2—C16—C32	5.6 (6)	C5—C6—C13—C14	−64.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg4i	0.93	2.83	3.625 (5)	144
C11—H11···Cg4ii	0.93	2.92	3.639 (5)	135
C24—H24···Cg2iii	0.93	2.98	3.730 (5)	139

Table 1

Hydrogen-bond geometry (, )

Cg2 and Cg4 are the centroids of rings C7-C12 and C23-C28, respectively.

DHA	DH	HA	D A	DHA
C8H8Cg4i	0.93	2.83	3.625(5)	144
C11H11Cg4ii	0.93	2.92	3.639(5)	135
C24H24Cg2iii	0.93	2.98	3.730(5)	139

Symmetry codes: (i) ; (ii) ; (iii) .