2,4,6-Trimethyl-N-[1-(1H-pyrrol-2-yl)ethyl-idene]aniline.

There are two independent mol-ecules in the asymmetric unit of the title compound, C(15)H(18)N(2), each of which features a syn disposition of the N atoms. In each mol-ecule, the pyrrole and benzene rings are essentially perpendicular, with dihedral angles of 78.90 (9) and 79.96 (9)°. In the crystal, the independent mol-ecules are connected by a pair of pyrrole-imino N-H⋯N hydrogen bonds, forming a two-mol-ecule aggregate.

Related literature

For general background to the imino­pyrrole unit, see: Small et al. (1998 ▶); Su et al. (2009a ▶,b ▶); Britovsek et al. (2003 ▶); Dawson et al. (2000 ▶). For the pyrrole diimine unit, see: Matsuo et al. (2001 ▶) and for the pyrrole monoimine unit, see: He et al. (2009 ▶).

Experimental

Crystal data

C15H18N2

M = 226.31

Monoclinic,

a = 29.848 (4) Å

b = 7.9668 (11) Å

c = 26.325 (4) Å

β = 119.940 (2)°

V = 5424.6 (13) Å3

Z = 16

Mo Kα radiation

μ = 0.07 mm−1

T = 296 K

0.37 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.976, T max = 0.988

14702 measured reflections

5675 independent reflections

2837 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.159

S = 0.99

5675 reflections

316 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037774/tk5142sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037774/tk5142Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037774/tk5142Isup3.cml

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

C15H18N2	Z = 16
Mr = 226.31	F(000) = 1952
Monoclinic, C2/c	Dx = 1.108 Mg m−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.848 (4) Å	θ = 2.7–26.8°
b = 7.9668 (11) Å	µ = 0.07 mm−1
c = 26.325 (4) Å	T = 296 K
β = 119.940 (2)°	Block, colourless
V = 5424.6 (13) Å3	0.37 × 0.24 × 0.18 mm

Bruker APEXII CCD diffractometer	5675 independent reflections
Radiation source: fine-focus sealed tube	2837 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 26.8°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −37→37
Tmin = 0.976, Tmax = 0.988	k = −10→9
14702 measured reflections	l = −29→33

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.060P)2 + 0.950P] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.028
5675 reflections	Δρmax = 0.18 e Å−3
316 parameters	Δρmin = −0.14 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: 0.0019 (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
N1	0.17414 (8)	−0.0243 (2)	0.55671 (9)	0.0611 (6)
H1	0.1455	0.0292	0.5365	0.073*
N2	0.14363 (7)	0.1397 (2)	0.62945 (8)	0.0530 (5)
N3	0.03652 (7)	0.2001 (2)	0.52301 (9)	0.0578 (5)
H3	0.0668	0.1573	0.5437	0.069*
N4	0.08934 (7)	0.1824 (2)	0.45990 (8)	0.0541 (5)
C1	0.19777 (11)	−0.1177 (3)	0.53393 (13)	0.0735 (8)
H1A	0.1860	−0.1334	0.4942	0.088*
C2	0.24147 (12)	−0.1846 (3)	0.57869 (14)	0.0759 (8)
H2	0.2647	−0.2551	0.5754	0.091*
C3	0.24487 (10)	−0.1272 (3)	0.63084 (12)	0.0655 (7)
H3A	0.2712	−0.1520	0.6686	0.079*
C4	0.20241 (9)	−0.0274 (3)	0.61649 (11)	0.0523 (6)
C5	0.18741 (9)	0.0629 (3)	0.65329 (10)	0.0499 (6)
C6	0.22526 (10)	0.0608 (3)	0.71790 (10)	0.0679 (7)
H6A	0.2153	0.1429	0.7371	0.102*
H6B	0.2592	0.0866	0.7246	0.102*
H6C	0.2255	−0.0485	0.7334	0.102*
C7	0.12933 (8)	0.2298 (3)	0.66607 (9)	0.0461 (6)
C8	0.10410 (9)	0.1483 (3)	0.69156 (10)	0.0538 (6)
C9	0.08898 (9)	0.2413 (3)	0.72524 (10)	0.0576 (7)
H9	0.0721	0.1869	0.7422	0.069*
C10	0.09813 (9)	0.4116 (3)	0.73436 (10)	0.0551 (6)
C11	0.12191 (9)	0.4894 (3)	0.70688 (10)	0.0545 (6)
H11	0.1281	0.6042	0.7122	0.065*
C12	0.13682 (8)	0.4037 (3)	0.67175 (10)	0.0460 (6)
C13	0.09381 (12)	−0.0379 (3)	0.68352 (13)	0.0818 (9)
H13A	0.0751	−0.0717	0.7027	0.123*
H13B	0.1261	−0.0973	0.7003	0.123*
H13C	0.0737	−0.0632	0.6425	0.123*
C14	0.08290 (12)	0.5089 (3)	0.77271 (13)	0.0853 (9)
H14A	0.0486	0.4771	0.7635	0.128*
H14B	0.0837	0.6270	0.7658	0.128*
H14C	0.1067	0.4845	0.8132	0.128*
C15	0.16042 (10)	0.4941 (3)	0.64095 (12)	0.0648 (7)
H15A	0.1586	0.6130	0.6456	0.097*
H15B	0.1418	0.4664	0.6000	0.097*
H15C	0.1959	0.4609	0.6575	0.097*
C16	0.00067 (10)	0.2114 (3)	0.53974 (12)	0.0686 (8)
H16	0.0047	0.1752	0.5754	0.082*
C17	−0.04220 (10)	0.2844 (3)	0.49581 (12)	0.0675 (7)
H17	−0.0729	0.3060	0.4956	0.081*
C18	−0.03163 (9)	0.3212 (3)	0.45087 (11)	0.0633 (7)
H18	−0.0539	0.3733	0.4155	0.076*
C19	0.01769 (9)	0.2664 (3)	0.46857 (10)	0.0477 (6)
C20	0.04682 (9)	0.2658 (3)	0.43821 (10)	0.0513 (6)
C21	0.02468 (10)	0.3648 (4)	0.38190 (12)	0.0747 (8)
H21A	0.0480	0.3599	0.3668	0.112*
H21B	0.0200	0.4796	0.3894	0.112*
H21C	−0.0081	0.3180	0.3537	0.112*
C22	0.11795 (9)	0.1761 (3)	0.42984 (10)	0.0496 (6)
C23	0.10903 (9)	0.0452 (3)	0.39048 (11)	0.0588 (7)
C24	0.14020 (10)	0.0325 (3)	0.36587 (11)	0.0628 (7)
H24	0.1343	−0.0543	0.3396	0.075*
C25	0.17990 (9)	0.1440 (3)	0.37872 (11)	0.0573 (6)
C26	0.18833 (10)	0.2692 (3)	0.41837 (12)	0.0631 (7)
H26	0.2153	0.3441	0.4281	0.076*
C27	0.15826 (9)	0.2884 (3)	0.44436 (11)	0.0560 (6)
C28	0.06663 (12)	−0.0811 (4)	0.37605 (15)	0.0992 (11)
H28A	0.0669	−0.1642	0.3498	0.149*
H28B	0.0338	−0.0249	0.3577	0.149*
H28C	0.0722	−0.1344	0.4114	0.149*
C29	0.21288 (11)	0.1278 (4)	0.35027 (13)	0.0861 (9)
H29A	0.2454	0.1833	0.3740	0.129*
H29B	0.1954	0.1786	0.3121	0.129*
H29C	0.2189	0.0112	0.3466	0.129*
C30	0.16873 (12)	0.4276 (4)	0.48756 (14)	0.0938 (10)
H30A	0.1422	0.5113	0.4698	0.141*
H30B	0.2017	0.4773	0.4989	0.141*
H30C	0.1690	0.3828	0.5216	0.141*

	U11	U22	U33	U12	U13	U23
N1	0.0641 (14)	0.0634 (13)	0.0535 (13)	0.0138 (10)	0.0275 (12)	−0.0060 (11)
N2	0.0544 (13)	0.0537 (12)	0.0478 (12)	0.0072 (10)	0.0231 (10)	−0.0029 (9)
N3	0.0505 (12)	0.0746 (14)	0.0548 (13)	0.0111 (10)	0.0311 (11)	0.0053 (11)
N4	0.0511 (12)	0.0681 (13)	0.0496 (12)	0.0031 (10)	0.0302 (11)	−0.0017 (10)
C1	0.086 (2)	0.0714 (18)	0.0683 (19)	0.0134 (16)	0.0419 (18)	−0.0145 (15)
C2	0.080 (2)	0.0676 (18)	0.091 (2)	0.0182 (15)	0.051 (2)	−0.0020 (17)
C3	0.0669 (17)	0.0607 (16)	0.0685 (18)	0.0152 (14)	0.0334 (15)	0.0070 (14)
C4	0.0565 (15)	0.0469 (14)	0.0550 (16)	0.0057 (11)	0.0290 (13)	0.0022 (12)
C5	0.0534 (15)	0.0474 (13)	0.0476 (14)	0.0027 (12)	0.0243 (13)	0.0019 (11)
C6	0.0625 (17)	0.0840 (19)	0.0529 (16)	0.0136 (14)	0.0256 (14)	0.0061 (14)
C7	0.0441 (13)	0.0492 (14)	0.0386 (13)	0.0055 (11)	0.0157 (11)	−0.0008 (11)
C8	0.0566 (15)	0.0509 (15)	0.0505 (15)	−0.0007 (12)	0.0241 (13)	0.0010 (12)
C9	0.0607 (16)	0.0672 (17)	0.0491 (15)	0.0000 (13)	0.0306 (13)	0.0087 (13)
C10	0.0570 (15)	0.0602 (16)	0.0479 (15)	0.0095 (12)	0.0261 (13)	−0.0007 (12)
C11	0.0569 (15)	0.0461 (14)	0.0578 (16)	0.0020 (11)	0.0266 (14)	−0.0009 (12)
C12	0.0416 (13)	0.0491 (14)	0.0447 (13)	0.0073 (10)	0.0196 (11)	0.0050 (11)
C13	0.102 (2)	0.0559 (17)	0.093 (2)	−0.0117 (16)	0.052 (2)	−0.0010 (16)
C14	0.106 (2)	0.093 (2)	0.074 (2)	0.0111 (18)	0.058 (2)	−0.0090 (17)
C15	0.0612 (16)	0.0644 (17)	0.0787 (19)	0.0026 (13)	0.0422 (16)	0.0043 (14)
C16	0.0639 (18)	0.091 (2)	0.0681 (18)	0.0114 (15)	0.0458 (17)	0.0108 (16)
C17	0.0550 (17)	0.088 (2)	0.0724 (19)	0.0064 (14)	0.0413 (16)	−0.0015 (16)
C18	0.0501 (15)	0.0796 (18)	0.0580 (16)	0.0102 (13)	0.0253 (14)	0.0041 (14)
C19	0.0461 (14)	0.0558 (14)	0.0424 (14)	−0.0003 (11)	0.0231 (12)	−0.0013 (12)
C20	0.0483 (15)	0.0582 (15)	0.0469 (14)	−0.0026 (12)	0.0235 (12)	−0.0047 (12)
C21	0.0650 (18)	0.096 (2)	0.0638 (18)	0.0155 (15)	0.0324 (15)	0.0206 (16)
C22	0.0490 (14)	0.0601 (15)	0.0439 (13)	0.0045 (12)	0.0263 (12)	0.0000 (12)
C23	0.0562 (15)	0.0745 (17)	0.0548 (15)	−0.0115 (13)	0.0345 (14)	−0.0128 (14)
C24	0.0662 (17)	0.0772 (18)	0.0537 (16)	−0.0068 (14)	0.0364 (15)	−0.0142 (14)
C25	0.0545 (16)	0.0723 (17)	0.0547 (16)	0.0036 (13)	0.0344 (14)	0.0014 (14)
C26	0.0566 (16)	0.0676 (17)	0.0726 (18)	−0.0109 (13)	0.0378 (15)	−0.0057 (15)
C27	0.0519 (15)	0.0628 (16)	0.0556 (15)	−0.0032 (12)	0.0284 (13)	−0.0073 (13)
C28	0.098 (2)	0.111 (2)	0.117 (3)	−0.046 (2)	0.074 (2)	−0.049 (2)
C29	0.083 (2)	0.110 (2)	0.093 (2)	−0.0015 (18)	0.064 (2)	0.0007 (19)
C30	0.091 (2)	0.093 (2)	0.108 (3)	−0.0230 (18)	0.058 (2)	−0.042 (2)

N1—C1	1.354 (3)	C14—H14B	0.9600
N1—C4	1.365 (3)	C14—H14C	0.9600
N1—H1	0.8600	C15—H15A	0.9600
N2—C5	1.287 (3)	C15—H15B	0.9600
N2—C7	1.427 (3)	C15—H15C	0.9600
N3—C16	1.348 (3)	C16—C17	1.355 (4)
N3—C19	1.358 (3)	C16—H16	0.9300
N3—H3	0.8600	C17—C18	1.399 (3)
N4—C20	1.286 (3)	C17—H17	0.9300
N4—C22	1.426 (3)	C18—C19	1.375 (3)
C1—C2	1.356 (4)	C18—H18	0.9300
C1—H1A	0.9300	C19—C20	1.445 (3)
C2—C3	1.402 (3)	C20—C21	1.510 (3)
C2—H2	0.9300	C21—H21A	0.9600
C3—C4	1.380 (3)	C21—H21B	0.9600
C3—H3A	0.9300	C21—H21C	0.9600
C4—C5	1.445 (3)	C22—C27	1.391 (3)
C5—C6	1.500 (3)	C22—C23	1.399 (3)
C6—H6A	0.9600	C23—C24	1.377 (3)
C6—H6B	0.9600	C23—C28	1.509 (3)
C6—H6C	0.9600	C24—C25	1.381 (3)
C7—C8	1.394 (3)	C24—H24	0.9300
C7—C12	1.400 (3)	C25—C26	1.374 (3)
C8—C9	1.392 (3)	C25—C29	1.511 (3)
C8—C13	1.508 (3)	C26—C27	1.382 (3)
C9—C10	1.381 (3)	C26—H26	0.9300
C9—H9	0.9300	C27—C30	1.505 (3)
C10—C11	1.387 (3)	C28—H28A	0.9600
C10—C14	1.512 (3)	C28—H28B	0.9600
C11—C12	1.389 (3)	C28—H28C	0.9600
C11—H11	0.9300	C29—H29A	0.9600
C12—C15	1.498 (3)	C29—H29B	0.9600
C13—H13A	0.9600	C29—H29C	0.9600
C13—H13B	0.9600	C30—H30A	0.9600
C13—H13C	0.9600	C30—H30B	0.9600
C14—H14A	0.9600	C30—H30C	0.9600
C1—N1—C4	110.0 (2)	H15A—C15—H15B	109.5
C1—N1—H1	125.0	C12—C15—H15C	109.5
C4—N1—H1	125.0	H15A—C15—H15C	109.5
C5—N2—C7	118.86 (19)	H15B—C15—H15C	109.5
C16—N3—C19	109.9 (2)	N3—C16—C17	108.4 (2)
C16—N3—H3	125.0	N3—C16—H16	125.8
C19—N3—H3	125.0	C17—C16—H16	125.8
C20—N4—C22	120.2 (2)	C16—C17—C18	107.2 (2)
N1—C1—C2	108.6 (2)	C16—C17—H17	126.4
N1—C1—H1A	125.7	C18—C17—H17	126.4
C2—C1—H1A	125.7	C19—C18—C17	107.6 (2)
C1—C2—C3	106.9 (2)	C19—C18—H18	126.2
C1—C2—H2	126.5	C17—C18—H18	126.2
C3—C2—H2	126.5	N3—C19—C18	106.88 (19)
C4—C3—C2	108.2 (3)	N3—C19—C20	122.4 (2)
C4—C3—H3A	125.9	C18—C19—C20	130.7 (2)
C2—C3—H3A	125.9	N4—C20—C19	119.3 (2)
N1—C4—C3	106.3 (2)	N4—C20—C21	123.9 (2)
N1—C4—C5	122.9 (2)	C19—C20—C21	116.9 (2)
C3—C4—C5	130.7 (2)	C20—C21—H21A	109.5
N2—C5—C4	119.2 (2)	C20—C21—H21B	109.5
N2—C5—C6	124.4 (2)	H21A—C21—H21B	109.5
C4—C5—C6	116.4 (2)	C20—C21—H21C	109.5
C5—C6—H6A	109.5	H21A—C21—H21C	109.5
C5—C6—H6B	109.5	H21B—C21—H21C	109.5
H6A—C6—H6B	109.5	C27—C22—C23	120.1 (2)
C5—C6—H6C	109.5	C27—C22—N4	120.0 (2)
H6A—C6—H6C	109.5	C23—C22—N4	119.5 (2)
H6B—C6—H6C	109.5	C24—C23—C22	118.7 (2)
C8—C7—C12	120.3 (2)	C24—C23—C28	120.7 (2)
C8—C7—N2	120.5 (2)	C22—C23—C28	120.6 (2)
C12—C7—N2	119.0 (2)	C23—C24—C25	122.4 (2)
C9—C8—C7	118.9 (2)	C23—C24—H24	118.8
C9—C8—C13	120.3 (2)	C25—C24—H24	118.8
C7—C8—C13	120.8 (2)	C26—C25—C24	117.5 (2)
C10—C9—C8	122.3 (2)	C26—C25—C29	121.4 (2)
C10—C9—H9	118.8	C24—C25—C29	121.0 (2)
C8—C9—H9	118.8	C25—C26—C27	122.6 (2)
C9—C10—C11	117.2 (2)	C25—C26—H26	118.7
C9—C10—C14	121.4 (2)	C27—C26—H26	118.7
C11—C10—C14	121.4 (2)	C26—C27—C22	118.6 (2)
C12—C11—C10	123.0 (2)	C26—C27—C30	120.9 (2)
C12—C11—H11	118.5	C22—C27—C30	120.4 (2)
C10—C11—H11	118.5	C23—C28—H28A	109.5
C11—C12—C7	118.1 (2)	C23—C28—H28B	109.5
C11—C12—C15	121.2 (2)	H28A—C28—H28B	109.5
C7—C12—C15	120.8 (2)	C23—C28—H28C	109.5
C8—C13—H13A	109.5	H28A—C28—H28C	109.5
C8—C13—H13B	109.5	H28B—C28—H28C	109.5
H13A—C13—H13B	109.5	C25—C29—H29A	109.5
C8—C13—H13C	109.5	C25—C29—H29B	109.5
H13A—C13—H13C	109.5	H29A—C29—H29B	109.5
H13B—C13—H13C	109.5	C25—C29—H29C	109.5
C10—C14—H14A	109.5	H29A—C29—H29C	109.5
C10—C14—H14B	109.5	H29B—C29—H29C	109.5
H14A—C14—H14B	109.5	C27—C30—H30A	109.5
C10—C14—H14C	109.5	C27—C30—H30B	109.5
H14A—C14—H14C	109.5	H30A—C30—H30B	109.5
H14B—C14—H14C	109.5	C27—C30—H30C	109.5
C12—C15—H15A	109.5	H30A—C30—H30C	109.5
C12—C15—H15B	109.5	H30B—C30—H30C	109.5
C4—N1—C1—C2	0.7 (3)	C19—N3—C16—C17	0.5 (3)
N1—C1—C2—C3	−0.9 (3)	N3—C16—C17—C18	−0.9 (3)
C1—C2—C3—C4	0.7 (3)	C16—C17—C18—C19	1.0 (3)
C1—N1—C4—C3	−0.3 (3)	C16—N3—C19—C18	0.1 (3)
C1—N1—C4—C5	179.1 (2)	C16—N3—C19—C20	−177.5 (2)
C2—C3—C4—N1	−0.3 (3)	C17—C18—C19—N3	−0.7 (3)
C2—C3—C4—C5	−179.6 (2)	C17—C18—C19—C20	176.7 (2)
C7—N2—C5—C4	−179.47 (19)	C22—N4—C20—C19	178.2 (2)
C7—N2—C5—C6	0.0 (3)	C22—N4—C20—C21	−1.6 (4)
N1—C4—C5—N2	5.5 (3)	N3—C19—C20—N4	8.6 (4)
C3—C4—C5—N2	−175.4 (2)	C18—C19—C20—N4	−168.4 (2)
N1—C4—C5—C6	−174.0 (2)	N3—C19—C20—C21	−171.6 (2)
C3—C4—C5—C6	5.1 (4)	C18—C19—C20—C21	11.4 (4)
C5—N2—C7—C8	−87.0 (3)	C20—N4—C22—C27	94.9 (3)
C5—N2—C7—C12	98.7 (3)	C20—N4—C22—C23	−92.1 (3)
C12—C7—C8—C9	−3.4 (3)	C27—C22—C23—C24	−1.2 (4)
N2—C7—C8—C9	−177.6 (2)	N4—C22—C23—C24	−174.2 (2)
C12—C7—C8—C13	177.4 (2)	C27—C22—C23—C28	177.8 (3)
N2—C7—C8—C13	3.1 (3)	N4—C22—C23—C28	4.8 (4)
C7—C8—C9—C10	−0.1 (4)	C22—C23—C24—C25	0.1 (4)
C13—C8—C9—C10	179.2 (2)	C28—C23—C24—C25	−178.9 (3)
C8—C9—C10—C11	2.0 (4)	C23—C24—C25—C26	1.1 (4)
C8—C9—C10—C14	−178.0 (2)	C23—C24—C25—C29	−179.1 (2)
C9—C10—C11—C12	−0.5 (3)	C24—C25—C26—C27	−1.2 (4)
C14—C10—C11—C12	179.4 (2)	C29—C25—C26—C27	179.0 (2)
C10—C11—C12—C7	−2.8 (3)	C25—C26—C27—C22	0.2 (4)
C10—C11—C12—C15	177.5 (2)	C25—C26—C27—C30	−179.9 (3)
C8—C7—C12—C11	4.7 (3)	C23—C22—C27—C26	1.1 (4)
N2—C7—C12—C11	179.01 (19)	N4—C22—C27—C26	174.1 (2)
C8—C7—C12—C15	−175.5 (2)	C23—C22—C27—C30	−178.8 (3)
N2—C7—C12—C15	−1.2 (3)	N4—C22—C27—C30	−5.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.86	2.23	3.029 (3)	154
N3—H3···N2	0.86	2.28	3.060 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4	0.86	2.23	3.029 (3)	154
N3—H3⋯N2	0.86	2.28	3.060 (3)	151