1,4-Bis(2,2':6',2''-terpyridin-4'-yl)benzene.

The asymmetric unit of the title compound, C(36)H(24)N(6), comprises a whole mol-ecule. Supra-molecular inter-actions between neighbouring mol-ecules are essentially π-π stacking inter-actions with small inter-planar distances [3.5140 (15) and 3.6041 (15) Å]. The central phenyl-ene ring is tilted with respect to the two pyridine substituents, subtending angles of 36.17 (11) and 34.95 (11)°. Three of the peripheral pyridine substituents are almost coplanar with the central pyridines [dihedral angles = 5.10 (12)-8.21 (12)°], but one subtends an angle of 24.86 (12)°.

Related literature

For coordination polymers having the title compound as a bridging ligand, see: Jones et al. (2010 ▶); Koo et al. (2003 ▶). For oligomeric coordination compounds having the title compound as bridging ligand, see: Maekawa et al. (2004 ▶); Schmittel et al. (2005 ▶, 2006 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For related work from our research group showing the motivation to use aromatic ligands for the design of photoluminescent materials, see: Girginova et al. (2007 ▶); Lima et al. (2006 ▶, 2009 ▶); Shi et al. (2008 ▶). For absolute structure, see: Flack (1983 ▶).

Experimental

Crystal data

C36H24N6

M = 540.61

Orthorhombic,

a = 9.8493 (2) Å

b = 10.0626 (2) Å

c = 26.0488 (4) Å

V = 2581.69 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.30 × 0.14 × 0.10 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.975, T max = 0.992

39767 measured reflections

3543 independent reflections

2856 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.108

S = 1.03

3543 reflections

379 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810047598/sj5055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047598/sj5055Isup2.hkl

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

C36H24N6	F(000) = 1128
Mr = 540.61	Dx = 1.391 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 7316 reflections
a = 9.8493 (2) Å	θ = 2.6–30.5°
b = 10.0626 (2) Å	µ = 0.09 mm−1
c = 26.0488 (4) Å	T = 100 K
V = 2581.69 (8) Å3	Needle, yellow
Z = 4	0.30 × 0.14 × 0.10 mm

Bruker X8 Kappa CCD APEXII diffractometer	3543 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
graphite	Rint = 0.051
ω and φ scans	θmax = 29.1°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −13→13
Tmin = 0.975, Tmax = 0.992	k = −12→13
39767 measured reflections	l = −35→35

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0619P)2 + 0.5147P] where P = (Fo2 + 2Fc2)/3
3543 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.24 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
N1	0.0080 (2)	0.1240 (2)	1.05763 (10)	0.0216 (5)
N2	0.1785 (2)	−0.1486 (2)	0.99796 (8)	0.0138 (4)
N3	0.4382 (2)	−0.3393 (2)	0.93357 (9)	0.0161 (5)
N4	0.3246 (2)	0.8440 (2)	0.79223 (8)	0.0161 (4)
N5	0.58036 (19)	0.6498 (2)	0.72756 (8)	0.0139 (4)
N6	0.7630 (2)	0.3705 (2)	0.67575 (9)	0.0185 (5)
C1	−0.0869 (3)	0.1423 (3)	1.09389 (12)	0.0254 (6)
H1	−0.0994	0.2298	1.1068	0.030*
C2	−0.1674 (3)	0.0429 (3)	1.11374 (11)	0.0247 (7)
H2	−0.2318	0.0612	1.1400	0.030*
C3	−0.1519 (3)	−0.0839 (3)	1.09445 (11)	0.0249 (6)
H3	−0.2074	−0.1545	1.1065	0.030*
C4	−0.0542 (3)	−0.1068 (3)	1.05716 (11)	0.0196 (6)
H4	−0.0405	−0.1936	1.0437	0.024*
C5	0.0235 (3)	−0.0007 (3)	1.03974 (11)	0.0135 (6)
C6	0.1305 (2)	−0.0238 (3)	1.00011 (10)	0.0139 (5)
C7	0.1762 (2)	0.0775 (3)	0.96819 (9)	0.0130 (5)
H7	0.1399	0.1647	0.9711	0.016*
C8	0.2768 (2)	0.0490 (2)	0.93152 (10)	0.0124 (5)
C9	0.3273 (2)	−0.0802 (3)	0.92965 (10)	0.0130 (5)
H9	0.3951	−0.1033	0.9053	0.016*
C10	0.2773 (2)	−0.1756 (2)	0.96387 (9)	0.0120 (5)
C11	0.3327 (2)	−0.3128 (3)	0.96507 (10)	0.0131 (5)
C12	0.2785 (2)	−0.4083 (3)	0.99789 (11)	0.0171 (5)
H12	0.2052	−0.3865	1.0200	0.020*
C13	0.3326 (3)	−0.5349 (3)	0.99789 (11)	0.0194 (6)
H13	0.2958	−0.6019	1.0195	0.023*
C14	0.4407 (3)	−0.5626 (3)	0.96601 (10)	0.0173 (5)
H14	0.4802	−0.6487	0.9653	0.021*
C15	0.4901 (3)	−0.4621 (3)	0.93501 (10)	0.0174 (5)
H15	0.5654	−0.4813	0.9135	0.021*
C16	0.3286 (2)	0.1535 (2)	0.89638 (10)	0.0114 (5)
C17	0.2428 (2)	0.2517 (2)	0.87710 (10)	0.0136 (5)
H17	0.1497	0.2521	0.8866	0.016*
C18	0.2921 (2)	0.3487 (2)	0.84423 (9)	0.0131 (5)
H18	0.2322	0.4149	0.8314	0.016*
C19	0.4290 (2)	0.3503 (2)	0.82959 (10)	0.0129 (5)
C20	0.5147 (2)	0.2510 (2)	0.84861 (9)	0.0134 (5)
H20	0.6076	0.2498	0.8389	0.016*
C21	0.4653 (2)	0.1544 (2)	0.88147 (10)	0.0138 (5)
H21	0.5249	0.0878	0.8941	0.017*
C22	0.2717 (3)	0.9666 (3)	0.78992 (11)	0.0190 (5)
H22	0.1974	0.9866	0.8119	0.023*
C23	0.3183 (3)	1.0664 (3)	0.75761 (10)	0.0182 (5)
H23	0.2777	1.1520	0.7576	0.022*
C24	0.4259 (2)	1.0367 (3)	0.72547 (11)	0.0177 (5)
H24	0.4613	1.1024	0.7029	0.021*
C25	0.4817 (2)	0.9096 (3)	0.72653 (10)	0.0167 (5)
H25	0.5546	0.8867	0.7043	0.020*
C26	0.4289 (2)	0.8168 (3)	0.76062 (9)	0.0140 (5)
C27	0.4838 (2)	0.6781 (3)	0.76221 (10)	0.0128 (5)
C28	0.4334 (2)	0.5846 (3)	0.79641 (10)	0.0135 (5)
H28	0.3671	0.6093	0.8211	0.016*
C29	0.4810 (2)	0.4537 (3)	0.79421 (9)	0.0126 (5)
C30	0.5797 (2)	0.4234 (2)	0.75747 (9)	0.0130 (5)
H30	0.6146	0.3358	0.7546	0.016*
C31	0.6260 (2)	0.5240 (3)	0.72519 (10)	0.0128 (5)
C32	0.7287 (3)	0.4973 (2)	0.68450 (11)	0.0124 (6)
C33	0.7851 (3)	0.6012 (3)	0.65635 (11)	0.0227 (6)
H33	0.7599	0.6905	0.6634	0.027*
C34	0.8783 (3)	0.5732 (3)	0.61796 (11)	0.0245 (6)
H34	0.9148	0.6424	0.5973	0.029*
C35	0.9166 (3)	0.4438 (3)	0.61035 (11)	0.0197 (6)
H35	0.9834	0.4218	0.5854	0.024*
C36	0.8562 (3)	0.3464 (3)	0.63969 (10)	0.0203 (6)
H36	0.8824	0.2568	0.6339	0.024*

	U11	U22	U33	U12	U13	U23
N1	0.0219 (10)	0.0193 (12)	0.0237 (12)	0.0009 (9)	0.0076 (10)	−0.0004 (10)
N2	0.0137 (9)	0.0148 (11)	0.0130 (10)	−0.0008 (8)	0.0002 (8)	0.0022 (9)
N3	0.0167 (9)	0.0138 (11)	0.0178 (11)	0.0005 (8)	0.0022 (9)	0.0002 (9)
N4	0.0184 (10)	0.0131 (11)	0.0166 (11)	−0.0005 (8)	0.0013 (9)	0.0006 (9)
N5	0.0130 (9)	0.0134 (10)	0.0154 (10)	0.0005 (8)	−0.0012 (8)	0.0027 (9)
N6	0.0184 (10)	0.0171 (12)	0.0200 (11)	0.0015 (9)	0.0027 (9)	−0.0011 (9)
C1	0.0237 (13)	0.0263 (16)	0.0263 (15)	0.0038 (12)	0.0087 (12)	−0.0051 (12)
C2	0.0182 (12)	0.0396 (19)	0.0164 (13)	0.0049 (13)	0.0051 (11)	0.0043 (14)
C3	0.0190 (13)	0.0325 (17)	0.0230 (14)	−0.0020 (11)	0.0061 (11)	0.0105 (13)
C4	0.0188 (11)	0.0185 (13)	0.0216 (13)	−0.0015 (11)	0.0017 (11)	0.0036 (11)
C5	0.0121 (12)	0.0165 (16)	0.0118 (14)	0.0021 (9)	−0.0024 (11)	0.0021 (9)
C6	0.0112 (10)	0.0178 (12)	0.0127 (12)	−0.0022 (10)	−0.0005 (10)	0.0008 (11)
C7	0.0131 (10)	0.0124 (12)	0.0136 (11)	0.0006 (9)	−0.0011 (9)	0.0000 (10)
C8	0.0121 (11)	0.0131 (14)	0.0121 (12)	−0.0015 (10)	−0.0013 (9)	0.0021 (10)
C9	0.0122 (10)	0.0125 (12)	0.0143 (12)	−0.0010 (9)	0.0002 (9)	0.0013 (10)
C10	0.0128 (10)	0.0125 (12)	0.0107 (11)	−0.0009 (9)	−0.0001 (9)	0.0010 (9)
C11	0.0112 (10)	0.0134 (12)	0.0148 (11)	−0.0020 (9)	−0.0014 (9)	0.0027 (10)
C12	0.0151 (11)	0.0176 (14)	0.0185 (12)	0.0008 (10)	0.0025 (10)	0.0029 (12)
C13	0.0228 (13)	0.0142 (13)	0.0211 (14)	−0.0033 (12)	−0.0005 (11)	0.0049 (12)
C14	0.0197 (12)	0.0117 (13)	0.0206 (13)	0.0021 (10)	−0.0032 (10)	0.0002 (11)
C15	0.0177 (11)	0.0174 (14)	0.0172 (13)	0.0014 (11)	0.0013 (10)	−0.0011 (12)
C16	0.0126 (10)	0.0097 (12)	0.0120 (11)	−0.0008 (9)	0.0009 (9)	0.0005 (9)
C17	0.0109 (10)	0.0152 (12)	0.0147 (11)	−0.0007 (9)	0.0005 (9)	−0.0007 (10)
C18	0.0137 (10)	0.0116 (12)	0.0140 (12)	0.0017 (9)	−0.0015 (9)	0.0021 (10)
C19	0.0153 (11)	0.0128 (12)	0.0105 (11)	−0.0019 (9)	0.0013 (9)	−0.0002 (10)
C20	0.0113 (10)	0.0135 (12)	0.0153 (11)	−0.0004 (9)	0.0032 (9)	0.0008 (9)
C21	0.0141 (10)	0.0117 (12)	0.0156 (12)	0.0008 (9)	0.0002 (10)	0.0016 (10)
C22	0.0183 (12)	0.0172 (13)	0.0213 (14)	0.0023 (11)	0.0014 (11)	−0.0030 (12)
C23	0.0207 (12)	0.0121 (13)	0.0217 (14)	0.0006 (10)	−0.0018 (11)	0.0002 (11)
C24	0.0199 (12)	0.0156 (13)	0.0175 (13)	−0.0006 (11)	−0.0015 (11)	0.0034 (12)
C25	0.0179 (12)	0.0132 (13)	0.0189 (13)	−0.0010 (10)	0.0020 (10)	0.0025 (11)
C26	0.0139 (10)	0.0140 (12)	0.0140 (12)	−0.0011 (9)	−0.0019 (9)	−0.0007 (10)
C27	0.0112 (10)	0.0130 (12)	0.0140 (11)	−0.0015 (9)	−0.0012 (9)	0.0015 (10)
C28	0.0121 (10)	0.0152 (13)	0.0132 (12)	−0.0012 (9)	0.0007 (9)	0.0026 (10)
C29	0.0127 (11)	0.0131 (13)	0.0122 (12)	−0.0004 (10)	−0.0013 (9)	0.0022 (10)
C30	0.0140 (11)	0.0107 (12)	0.0143 (12)	−0.0004 (9)	−0.0002 (10)	0.0006 (10)
C31	0.0105 (10)	0.0164 (12)	0.0117 (12)	−0.0006 (10)	−0.0019 (10)	−0.0003 (11)
C32	0.0108 (11)	0.0164 (16)	0.0101 (14)	−0.0022 (9)	−0.0015 (11)	0.0014 (9)
C33	0.0267 (13)	0.0159 (14)	0.0254 (15)	0.0009 (11)	0.0075 (12)	0.0010 (11)
C34	0.0254 (13)	0.0274 (16)	0.0206 (14)	−0.0090 (12)	0.0057 (11)	0.0070 (12)
C35	0.0160 (11)	0.0290 (16)	0.0139 (12)	0.0010 (11)	0.0012 (10)	−0.0029 (12)
C36	0.0181 (12)	0.0209 (14)	0.0218 (14)	0.0027 (11)	0.0023 (11)	−0.0020 (11)

N1—C1	1.341 (4)	C15—H15	0.9500
N1—C5	1.347 (3)	C16—C17	1.393 (3)
N2—C6	1.342 (3)	C16—C21	1.402 (3)
N2—C10	1.345 (3)	C17—C18	1.386 (3)
N3—C15	1.337 (3)	C17—H17	0.9500
N3—C11	1.351 (3)	C18—C19	1.402 (3)
N4—C22	1.341 (3)	C18—H18	0.9500
N4—C26	1.344 (3)	C19—C20	1.399 (3)
N5—C27	1.342 (3)	C19—C29	1.482 (3)
N5—C31	1.344 (3)	C20—C21	1.383 (3)
N6—C36	1.335 (3)	C20—H20	0.9500
N6—C32	1.340 (3)	C21—H21	0.9500
C1—C2	1.377 (4)	C22—C23	1.388 (4)
C1—H1	0.9500	C22—H22	0.9500
C2—C3	1.380 (5)	C23—C24	1.383 (4)
C2—H2	0.9500	C23—H23	0.9500
C3—C4	1.387 (4)	C24—C25	1.393 (4)
C3—H3	0.9500	C24—H24	0.9500
C4—C5	1.389 (4)	C25—C26	1.390 (4)
C4—H4	0.9500	C25—H25	0.9500
C5—C6	1.493 (4)	C26—C27	1.497 (3)
C6—C7	1.391 (4)	C27—C28	1.388 (3)
C7—C8	1.406 (3)	C28—C29	1.399 (4)
C7—H7	0.9500	C28—H28	0.9500
C8—C9	1.392 (3)	C29—C30	1.397 (3)
C8—C16	1.485 (3)	C30—C31	1.393 (4)
C9—C10	1.400 (3)	C30—H30	0.9500
C9—H9	0.9500	C31—C32	1.490 (4)
C10—C11	1.484 (3)	C32—C33	1.393 (4)
C11—C12	1.392 (4)	C33—C34	1.386 (4)
C12—C13	1.381 (4)	C33—H33	0.9500
C12—H12	0.9500	C34—C35	1.370 (4)
C13—C14	1.379 (4)	C34—H34	0.9500
C13—H13	0.9500	C35—C36	1.378 (4)
C14—C15	1.383 (4)	C35—H35	0.9500
C14—H14	0.9500	C36—H36	0.9500
C1—N1—C5	116.7 (2)	C17—C18—C19	120.9 (2)
C6—N2—C10	118.1 (2)	C17—C18—H18	119.6
C15—N3—C11	117.4 (2)	C19—C18—H18	119.6
C22—N4—C26	117.2 (2)	C20—C19—C18	118.4 (2)
C27—N5—C31	117.9 (2)	C20—C19—C29	120.9 (2)
C36—N6—C32	117.8 (2)	C18—C19—C29	120.7 (2)
N1—C1—C2	124.5 (3)	C21—C20—C19	120.6 (2)
N1—C1—H1	117.8	C21—C20—H20	119.7
C2—C1—H1	117.8	C19—C20—H20	119.7
C1—C2—C3	118.1 (3)	C20—C21—C16	120.9 (2)
C1—C2—H2	120.9	C20—C21—H21	119.5
C3—C2—H2	120.9	C16—C21—H21	119.5
C2—C3—C4	119.0 (3)	N4—C22—C23	124.3 (2)
C2—C3—H3	120.5	N4—C22—H22	117.8
C4—C3—H3	120.5	C23—C22—H22	117.8
C3—C4—C5	118.9 (3)	C24—C23—C22	117.7 (3)
C3—C4—H4	120.5	C24—C23—H23	121.1
C5—C4—H4	120.5	C22—C23—H23	121.1
N1—C5—C4	122.7 (2)	C23—C24—C25	119.2 (3)
N1—C5—C6	117.6 (2)	C23—C24—H24	120.4
C4—C5—C6	119.6 (2)	C25—C24—H24	120.4
N2—C6—C7	123.1 (2)	C26—C25—C24	118.8 (2)
N2—C6—C5	115.0 (2)	C26—C25—H25	120.6
C7—C6—C5	121.8 (2)	C24—C25—H25	120.6
C6—C7—C8	119.0 (2)	N4—C26—C25	122.7 (2)
C6—C7—H7	120.5	N4—C26—C27	116.7 (2)
C8—C7—H7	120.5	C25—C26—C27	120.6 (2)
C9—C8—C7	117.8 (2)	N5—C27—C28	122.8 (2)
C9—C8—C16	121.1 (2)	N5—C27—C26	115.8 (2)
C7—C8—C16	121.1 (2)	C28—C27—C26	121.4 (2)
C8—C9—C10	119.5 (2)	C27—C28—C29	119.5 (2)
C8—C9—H9	120.2	C27—C28—H28	120.3
C10—C9—H9	120.2	C29—C28—H28	120.3
N2—C10—C9	122.4 (2)	C30—C29—C28	117.8 (2)
N2—C10—C11	116.1 (2)	C30—C29—C19	120.9 (2)
C9—C10—C11	121.5 (2)	C28—C29—C19	121.3 (2)
N3—C11—C12	122.1 (2)	C31—C30—C29	118.9 (2)
N3—C11—C10	117.0 (2)	C31—C30—H30	120.6
C12—C11—C10	120.9 (2)	C29—C30—H30	120.6
C13—C12—C11	119.3 (2)	N5—C31—C30	123.2 (2)
C13—C12—H12	120.4	N5—C31—C32	115.4 (2)
C11—C12—H12	120.4	C30—C31—C32	121.4 (2)
C14—C13—C12	119.0 (3)	N6—C32—C33	121.6 (2)
C14—C13—H13	120.5	N6—C32—C31	117.7 (2)
C12—C13—H13	120.5	C33—C32—C31	120.7 (2)
C13—C14—C15	118.4 (2)	C34—C33—C32	119.5 (3)
C13—C14—H14	120.8	C34—C33—H33	120.3
C15—C14—H14	120.8	C32—C33—H33	120.3
N3—C15—C14	123.9 (2)	C35—C34—C33	118.6 (3)
N3—C15—H15	118.1	C35—C34—H34	120.7
C14—C15—H15	118.1	C33—C34—H34	120.7
C17—C16—C21	118.6 (2)	C34—C35—C36	118.5 (2)
C17—C16—C8	121.1 (2)	C34—C35—H35	120.8
C21—C16—C8	120.4 (2)	C36—C35—H35	120.8
C18—C17—C16	120.6 (2)	N6—C36—C35	123.9 (3)
C18—C17—H17	119.7	N6—C36—H36	118.0
C16—C17—H17	119.7	C35—C36—H36	118.0
C5—N1—C1—C2	0.4 (4)	C18—C19—C20—C21	−0.6 (4)
N1—C1—C2—C3	−1.4 (5)	C29—C19—C20—C21	−179.7 (2)
C1—C2—C3—C4	1.7 (4)	C19—C20—C21—C16	0.1 (4)
C2—C3—C4—C5	−1.1 (4)	C17—C16—C21—C20	0.4 (4)
C1—N1—C5—C4	0.3 (4)	C8—C16—C21—C20	179.8 (2)
C1—N1—C5—C6	−178.8 (3)	C26—N4—C22—C23	−0.6 (4)
C3—C4—C5—N1	0.1 (4)	N4—C22—C23—C24	0.4 (4)
C3—C4—C5—C6	179.2 (2)	C22—C23—C24—C25	0.5 (4)
C10—N2—C6—C7	1.3 (4)	C23—C24—C25—C26	−1.1 (4)
C10—N2—C6—C5	−178.6 (2)	C22—N4—C26—C25	−0.1 (4)
N1—C5—C6—N2	155.2 (2)	C22—N4—C26—C27	−177.9 (2)
C4—C5—C6—N2	−23.9 (4)	C24—C25—C26—N4	0.9 (4)
N1—C5—C6—C7	−24.6 (4)	C24—C25—C26—C27	178.6 (2)
C4—C5—C6—C7	156.3 (3)	C31—N5—C27—C28	2.3 (3)
N2—C6—C7—C8	0.4 (4)	C31—N5—C27—C26	−175.5 (2)
C5—C6—C7—C8	−179.7 (2)	N4—C26—C27—N5	174.9 (2)
C6—C7—C8—C9	−0.9 (3)	C25—C26—C27—N5	−3.0 (3)
C6—C7—C8—C16	179.7 (2)	N4—C26—C27—C28	−2.9 (3)
C7—C8—C9—C10	−0.2 (3)	C25—C26—C27—C28	179.2 (2)
C16—C8—C9—C10	179.1 (2)	N5—C27—C28—C29	−2.0 (4)
C6—N2—C10—C9	−2.5 (4)	C26—C27—C28—C29	175.6 (2)
C6—N2—C10—C11	176.5 (2)	C27—C28—C29—C30	0.7 (4)
C8—C9—C10—N2	2.0 (4)	C27—C28—C29—C19	−179.3 (2)
C8—C9—C10—C11	−177.0 (2)	C20—C19—C29—C30	35.9 (4)
C15—N3—C11—C12	−0.2 (4)	C18—C19—C29—C30	−143.2 (2)
C15—N3—C11—C10	178.9 (2)	C20—C19—C29—C28	−144.0 (2)
N2—C10—C11—N3	−175.6 (2)	C18—C19—C29—C28	36.9 (4)
C9—C10—C11—N3	3.4 (3)	C28—C29—C30—C31	0.2 (3)
N2—C10—C11—C12	3.5 (3)	C19—C29—C30—C31	−179.7 (2)
C9—C10—C11—C12	−177.5 (2)	C27—N5—C31—C30	−1.3 (4)
N3—C11—C12—C13	−1.0 (4)	C27—N5—C31—C32	177.4 (2)
C10—C11—C12—C13	179.9 (2)	C29—C30—C31—N5	0.0 (4)
C11—C12—C13—C14	1.2 (4)	C29—C30—C31—C32	−178.6 (2)
C12—C13—C14—C15	−0.4 (4)	C36—N6—C32—C33	1.5 (4)
C11—N3—C15—C14	1.1 (4)	C36—N6—C32—C31	−179.3 (2)
C13—C14—C15—N3	−0.9 (4)	N5—C31—C32—N6	−170.8 (2)
C9—C8—C16—C17	144.8 (2)	C30—C31—C32—N6	8.0 (4)
C7—C8—C16—C17	−35.9 (3)	N5—C31—C32—C33	8.5 (4)
C9—C8—C16—C21	−34.6 (4)	C30—C31—C32—C33	−172.8 (3)
C7—C8—C16—C21	144.7 (2)	N6—C32—C33—C34	0.6 (4)
C21—C16—C17—C18	−0.5 (3)	C31—C32—C33—C34	−178.6 (3)
C8—C16—C17—C18	−179.9 (2)	C32—C33—C34—C35	−2.8 (4)
C16—C17—C18—C19	0.0 (4)	C33—C34—C35—C36	2.9 (4)
C17—C18—C19—C20	0.5 (4)	C32—N6—C36—C35	−1.4 (4)
C17—C18—C19—C29	179.7 (2)	C34—C35—C36—N6	−0.8 (4)