N,N'-Bis[3,5-bis-(2,6-diisopropyl-phen-yl)phen-yl]butane-2,3-diimine.

The title mol-ecule, C(64)H(80)N(2), lies on an inversion center wherein the central butane-diimine fragment [N=C(Me)-C(Me)=N] is essentially planar [maximum deviation = 0.002 (2) Å] and its mean plane forms a dihedral of 70.88 (10)° with the attached benzene ring. In the symmetry-unique part of the mol-ecule, the dihedral angles between the benzene ring bonded to the N atom and the other two benzene rings are 89.61 (6) and 82.77 (6)°.

Related literature

For background to water splitting, see: Yang & Hall (2010 ▶); Kee et al. (2011 ▶); Blakemore et al. (2010 ▶). For related structures, see: Ionkin & Marshall (2004 ▶); Zou et al. (2008 ▶); Lohr et al. (2011 ▶).

Experimental

Crystal data

C64H80N2

M = 877.30

Triclinic,

a = 8.512 (3) Å

b = 11.513 (3) Å

c = 16.501 (6) Å

α = 101.456 (18)°

β = 97.471 (13)°

γ = 99.505 (17)°

V = 1540.8 (9) Å3

Z = 1

Mo Kα radiation

μ = 0.05 mm−1

T = 173 K

0.16 × 0.14 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII CCD detector

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.992, T max = 0.997

10648 measured reflections

5610 independent reflections

4274 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.197

S = 1.06

5610 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031254/lh5297sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031254/lh5297Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031254/lh5297Isup3.cml

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

C64H80N2	Z = 1
Mr = 877.30	F(000) = 478
Triclinic, P1	Dx = 0.945 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.512 (3) Å	Cell parameters from 6423 reflections
b = 11.513 (3) Å	θ = 1.0–25.4°
c = 16.501 (6) Å	µ = 0.05 mm−1
α = 101.456 (18)°	T = 173 K
β = 97.471 (13)°	Prism, pale yellow
γ = 99.505 (17)°	0.16 × 0.14 × 0.06 mm
V = 1540.8 (9) Å3

Nonius KappaCCD diffractometer with Bruker APEXII CCD detector	5610 independent reflections
Radiation source: fine-focus sealed tube	4274 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω and φ scans	θmax = 25.4°, θmin = 1.8°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −10→10
Tmin = 0.992, Tmax = 0.997	k = −12→13
10648 measured reflections	l = −19→19

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) = 0.197	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0937P)2 + 0.8313P] where P = (Fo2 + 2Fc2)/3
5610 reflections	(Δ/σ)max = 0.003
307 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. 1H NMR (400 MHz, CDCl3): δ = 1.08 (d, 24H, CH(CH3)2), 1.15 (d, 24H, CH(CH3)2), 2.23 (s, 6H, N═C–CH3), 2.84 (m, 8H, CH(CH3)2), 6.62 (d, 4H, Ar–H), 6.79 (t, 2H, Ar–H), 7.21 (d, 8H, Ar-H), 7.34 (t, 4H, Ar–H). 13C NMR (100 MHz, CDCl3): δ = 15.64 (N═C–CH3), 24.31 (CH(CH3)2), 24.44 (CH(CH3)2), 30.65 (CH(CH3)2), 118.09 (Ar–CH), 122.71 (Ar–CH), 126.91 (Ar–CH), 128.09 (Ar–CH), 139.08 (Ar–C), 141.66 (Ar–C), 146.84 (Ar–C), 150.89 (Ar–C), 169.06 (N═C–CH3).

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	0.0422 (2)	0.46436 (15)	0.09717 (11)	0.0335 (4)
C1	0.0718 (2)	0.49926 (18)	0.03123 (12)	0.0303 (5)
C2	0.2367 (3)	0.5377 (3)	0.01107 (16)	0.0541 (7)
H2A	0.2353	0.5091	−0.0491	0.065*
H2B	0.3152	0.5032	0.0429	0.065*
H2C	0.2674	0.6261	0.0262	0.065*
C3	0.1702 (2)	0.46292 (18)	0.16106 (12)	0.0295 (4)
C4	0.2616 (2)	0.56921 (18)	0.21263 (13)	0.0307 (5)
H4	0.2407	0.6449	0.2042	0.037*
C5	0.3836 (2)	0.56590 (17)	0.27654 (12)	0.0286 (4)
C6	0.4108 (2)	0.45436 (17)	0.28880 (12)	0.0278 (4)
H6	0.4941	0.4515	0.3323	0.033*
C7	0.3184 (2)	0.34646 (17)	0.23857 (12)	0.0272 (4)
C8	0.1969 (2)	0.35137 (18)	0.17475 (12)	0.0291 (4)
H8	0.1322	0.2787	0.1405	0.035*
C9	0.4870 (2)	0.68017 (17)	0.33082 (13)	0.0317 (5)
C10	0.6300 (3)	0.73029 (18)	0.30592 (14)	0.0374 (5)
C11	0.7271 (3)	0.8346 (2)	0.35794 (17)	0.0466 (6)
H11	0.8251	0.8689	0.3425	0.056*
C12	0.6828 (3)	0.8886 (2)	0.43142 (17)	0.0519 (7)
H12	0.7500	0.9602	0.4658	0.062*
C13	0.5419 (3)	0.8399 (2)	0.45557 (15)	0.0468 (6)
H13	0.5125	0.8787	0.5062	0.056*
C14	0.4423 (3)	0.73418 (19)	0.40628 (13)	0.0370 (5)
C15	0.6785 (3)	0.6753 (2)	0.22388 (16)	0.0466 (6)
H15	0.6063	0.5943	0.2010	0.056*
C16	0.6502 (5)	0.7543 (3)	0.1599 (2)	0.0793 (10)
H16A	0.6741	0.7153	0.1058	0.095*
H16B	0.7214	0.8339	0.1802	0.095*
H16C	0.5373	0.7639	0.1532	0.095*
C17	0.8506 (4)	0.6567 (4)	0.2347 (3)	0.0946 (12)
H17A	0.8753	0.6198	0.1802	0.114*
H17B	0.8642	0.6033	0.2734	0.114*
H17C	0.9240	0.7348	0.2574	0.114*
C18	0.2893 (3)	0.6814 (2)	0.43511 (14)	0.0420 (5)
H18	0.2390	0.6038	0.3939	0.050*
C19	0.3249 (4)	0.6521 (3)	0.52078 (18)	0.0652 (8)
H19A	0.2246	0.6125	0.5352	0.078*
H19B	0.3705	0.7269	0.5631	0.078*
H19C	0.4025	0.5979	0.5193	0.078*
C20	0.1674 (4)	0.7648 (3)	0.4347 (2)	0.0641 (8)
H20A	0.0657	0.7246	0.4474	0.077*
H20B	0.1480	0.7835	0.3793	0.077*
H20C	0.2103	0.8398	0.4773	0.077*
C21	0.3505 (2)	0.22790 (17)	0.25381 (13)	0.0299 (5)
C22	0.2565 (3)	0.16664 (18)	0.30220 (14)	0.0350 (5)
C23	0.2938 (3)	0.0592 (2)	0.31816 (15)	0.0437 (6)
H23	0.2319	0.0170	0.3511	0.052*
C24	0.4189 (3)	0.0126 (2)	0.28706 (16)	0.0487 (6)
H24	0.4431	−0.0604	0.2991	0.058*
C25	0.5085 (3)	0.0721 (2)	0.23850 (16)	0.0458 (6)
H25	0.5936	0.0389	0.2168	0.055*
C26	0.4766 (3)	0.18020 (18)	0.22058 (14)	0.0361 (5)
C27	0.1190 (3)	0.2182 (2)	0.33720 (16)	0.0427 (6)
H27	0.0728	0.2616	0.2958	0.051*
C28	0.1793 (3)	0.3116 (2)	0.42019 (17)	0.0512 (6)
H28A	0.0904	0.3498	0.4371	0.061*
H28B	0.2673	0.3734	0.4130	0.061*
H28C	0.2189	0.2714	0.4636	0.061*
C29	−0.0188 (3)	0.1216 (3)	0.3474 (2)	0.0591 (7)
H29A	−0.1114	0.1585	0.3595	0.071*
H29B	0.0173	0.0855	0.3938	0.071*
H29C	−0.0507	0.0587	0.2954	0.071*
C30	0.5731 (3)	0.2413 (2)	0.16369 (16)	0.0451 (6)
H30	0.5383	0.3200	0.1632	0.054*
C31	0.7519 (4)	0.2698 (4)	0.1956 (3)	0.1020 (15)
H31A	0.8079	0.3124	0.1585	0.122*
H31B	0.7908	0.1945	0.1968	0.122*
H31C	0.7738	0.3211	0.2524	0.122*
C32	0.5319 (6)	0.1666 (4)	0.0742 (2)	0.1061 (15)
H32A	0.5925	0.2083	0.0382	0.127*
H32B	0.4158	0.1560	0.0541	0.127*
H32C	0.5608	0.0873	0.0725	0.127*

	U11	U22	U33	U12	U13	U23
N1	0.0301 (9)	0.0400 (10)	0.0312 (10)	0.0074 (7)	−0.0019 (7)	0.0138 (8)
C1	0.0313 (11)	0.0313 (10)	0.0286 (11)	0.0088 (8)	0.0014 (9)	0.0074 (8)
C2	0.0316 (12)	0.093 (2)	0.0397 (14)	0.0075 (12)	0.0007 (10)	0.0285 (14)
C3	0.0246 (10)	0.0375 (11)	0.0286 (11)	0.0064 (8)	0.0043 (8)	0.0128 (9)
C4	0.0326 (11)	0.0319 (10)	0.0302 (11)	0.0097 (8)	0.0035 (8)	0.0117 (8)
C5	0.0314 (10)	0.0290 (10)	0.0267 (10)	0.0076 (8)	0.0049 (8)	0.0078 (8)
C6	0.0261 (10)	0.0321 (10)	0.0251 (10)	0.0058 (8)	−0.0006 (8)	0.0092 (8)
C7	0.0254 (10)	0.0307 (10)	0.0265 (10)	0.0045 (8)	0.0035 (8)	0.0098 (8)
C8	0.0271 (10)	0.0296 (10)	0.0294 (11)	0.0023 (8)	0.0023 (8)	0.0077 (8)
C9	0.0364 (11)	0.0275 (10)	0.0310 (11)	0.0097 (8)	−0.0019 (9)	0.0083 (8)
C10	0.0391 (12)	0.0291 (10)	0.0425 (13)	0.0062 (9)	0.0003 (10)	0.0094 (9)
C11	0.0443 (13)	0.0325 (11)	0.0568 (16)	−0.0004 (10)	0.0009 (11)	0.0073 (11)
C12	0.0585 (16)	0.0284 (11)	0.0561 (16)	−0.0006 (11)	−0.0109 (13)	0.0008 (11)
C13	0.0632 (16)	0.0343 (12)	0.0376 (13)	0.0111 (11)	−0.0010 (11)	0.0009 (10)
C14	0.0451 (13)	0.0336 (11)	0.0321 (12)	0.0119 (9)	−0.0011 (9)	0.0079 (9)
C15	0.0421 (13)	0.0396 (12)	0.0538 (15)	0.0015 (10)	0.0132 (11)	0.0024 (11)
C16	0.107 (3)	0.072 (2)	0.064 (2)	0.0133 (19)	0.0287 (19)	0.0196 (16)
C17	0.063 (2)	0.120 (3)	0.092 (3)	0.037 (2)	0.0111 (19)	−0.012 (2)
C18	0.0510 (14)	0.0400 (12)	0.0347 (12)	0.0113 (10)	0.0077 (10)	0.0051 (10)
C19	0.0736 (19)	0.079 (2)	0.0486 (17)	0.0145 (16)	0.0124 (14)	0.0271 (15)
C20	0.0597 (17)	0.0632 (17)	0.076 (2)	0.0236 (14)	0.0172 (15)	0.0188 (15)
C21	0.0306 (10)	0.0269 (10)	0.0302 (11)	0.0051 (8)	−0.0021 (8)	0.0070 (8)
C22	0.0348 (11)	0.0327 (11)	0.0368 (12)	0.0023 (9)	0.0004 (9)	0.0133 (9)
C23	0.0505 (14)	0.0346 (11)	0.0473 (14)	0.0039 (10)	0.0033 (11)	0.0188 (10)
C24	0.0617 (16)	0.0318 (12)	0.0558 (15)	0.0148 (11)	0.0010 (12)	0.0181 (11)
C25	0.0482 (14)	0.0384 (12)	0.0532 (15)	0.0188 (10)	0.0048 (11)	0.0097 (11)
C26	0.0360 (12)	0.0315 (11)	0.0393 (12)	0.0073 (9)	0.0006 (9)	0.0073 (9)
C27	0.0364 (12)	0.0452 (13)	0.0540 (15)	0.0071 (10)	0.0116 (10)	0.0267 (11)
C28	0.0538 (15)	0.0447 (13)	0.0623 (17)	0.0130 (11)	0.0265 (13)	0.0154 (12)
C29	0.0464 (15)	0.0633 (17)	0.0720 (19)	0.0000 (13)	0.0172 (13)	0.0301 (15)
C30	0.0430 (13)	0.0446 (13)	0.0543 (15)	0.0151 (10)	0.0167 (11)	0.0153 (11)
C31	0.0421 (17)	0.141 (4)	0.144 (4)	0.0071 (19)	0.017 (2)	0.090 (3)
C32	0.157 (4)	0.088 (3)	0.063 (2)	−0.014 (3)	0.046 (2)	0.0058 (19)

N1—C1	1.273 (3)	C18—C19	1.522 (3)
N1—C3	1.419 (2)	C18—C20	1.525 (4)
C1—C1i	1.498 (4)	C18—H18	1.0000
C1—C2	1.500 (3)	C19—H19A	0.9800
C2—H2A	0.9800	C19—H19B	0.9800
C2—H2B	0.9800	C19—H19C	0.9800
C2—H2C	0.9800	C20—H20A	0.9800
C3—C4	1.388 (3)	C20—H20B	0.9800
C3—C8	1.397 (3)	C20—H20C	0.9800
C4—C5	1.391 (3)	C21—C22	1.407 (3)
C4—H4	0.9500	C21—C26	1.408 (3)
C5—C6	1.390 (3)	C22—C23	1.392 (3)
C5—C9	1.501 (3)	C22—C27	1.525 (3)
C6—C7	1.396 (3)	C23—C24	1.380 (4)
C6—H6	0.9500	C23—H23	0.9500
C7—C8	1.393 (3)	C24—C25	1.378 (4)
C7—C21	1.498 (3)	C24—H24	0.9500
C8—H8	0.9500	C25—C26	1.395 (3)
C9—C14	1.406 (3)	C25—H25	0.9500
C9—C10	1.405 (3)	C26—C30	1.524 (3)
C10—C11	1.393 (3)	C27—C29	1.529 (3)
C10—C15	1.515 (3)	C27—C28	1.531 (4)
C11—C12	1.377 (4)	C27—H27	1.0000
C11—H11	0.9500	C28—H28A	0.9800
C12—C13	1.379 (4)	C28—H28B	0.9800
C12—H12	0.9500	C28—H28C	0.9800
C13—C14	1.396 (3)	C29—H29A	0.9800
C13—H13	0.9500	C29—H29B	0.9800
C14—C18	1.518 (3)	C29—H29C	0.9800
C15—C17	1.508 (4)	C30—C31	1.504 (4)
C15—C16	1.545 (4)	C30—C32	1.518 (4)
C15—H15	1.0000	C30—H30	1.0000
C16—H16A	0.9800	C31—H31A	0.9800
C16—H16B	0.9800	C31—H31B	0.9800
C16—H16C	0.9800	C31—H31C	0.9800
C17—H17A	0.9800	C32—H32A	0.9800
C17—H17B	0.9800	C32—H32B	0.9800
C17—H17C	0.9800	C32—H32C	0.9800
C1—N1—C3	120.55 (18)	C19—C18—H18	107.5
N1—C1—C1i	116.3 (2)	C20—C18—H18	107.5
N1—C1—C2	125.69 (18)	C18—C19—H19A	109.5
C1i—C1—C2	118.0 (2)	C18—C19—H19B	109.5
C1—C2—H2A	109.5	H19A—C19—H19B	109.5
C1—C2—H2B	109.5	C18—C19—H19C	109.5
H2A—C2—H2B	109.5	H19A—C19—H19C	109.5
C1—C2—H2C	109.5	H19B—C19—H19C	109.5
H2A—C2—H2C	109.5	C18—C20—H20A	109.5
H2B—C2—H2C	109.5	C18—C20—H20B	109.5
C4—C3—C8	120.00 (17)	H20A—C20—H20B	109.5
C4—C3—N1	121.39 (17)	C18—C20—H20C	109.5
C8—C3—N1	118.50 (18)	H20A—C20—H20C	109.5
C3—C4—C5	120.56 (18)	H20B—C20—H20C	109.5
C3—C4—H4	119.7	C22—C21—C26	120.83 (18)
C5—C4—H4	119.7	C22—C21—C7	119.77 (18)
C6—C5—C4	118.94 (18)	C26—C21—C7	119.39 (17)
C6—C5—C9	119.98 (17)	C23—C22—C21	118.4 (2)
C4—C5—C9	121.07 (17)	C23—C22—C27	121.13 (19)
C5—C6—C7	121.37 (17)	C21—C22—C27	120.51 (18)
C5—C6—H6	119.3	C24—C23—C22	121.3 (2)
C7—C6—H6	119.3	C24—C23—H23	119.4
C8—C7—C6	118.96 (17)	C22—C23—H23	119.4
C8—C7—C21	121.08 (17)	C25—C24—C23	120.0 (2)
C6—C7—C21	119.95 (16)	C25—C24—H24	120.0
C7—C8—C3	120.13 (18)	C23—C24—H24	120.0
C7—C8—H8	119.9	C24—C25—C26	121.2 (2)
C3—C8—H8	119.9	C24—C25—H25	119.4
C14—C9—C10	120.88 (19)	C26—C25—H25	119.4
C14—C9—C5	120.06 (19)	C25—C26—C21	118.4 (2)
C10—C9—C5	119.04 (19)	C25—C26—C30	120.0 (2)
C11—C10—C9	118.5 (2)	C21—C26—C30	121.58 (18)
C11—C10—C15	119.7 (2)	C22—C27—C29	113.5 (2)
C9—C10—C15	121.77 (19)	C22—C27—C28	111.90 (19)
C12—C11—C10	120.8 (2)	C29—C27—C28	110.0 (2)
C12—C11—H11	119.6	C22—C27—H27	107.0
C10—C11—H11	119.6	C29—C27—H27	107.0
C11—C12—C13	120.7 (2)	C28—C27—H27	107.0
C11—C12—H12	119.7	C27—C28—H28A	109.5
C13—C12—H12	119.7	C27—C28—H28B	109.5
C12—C13—C14	120.6 (2)	H28A—C28—H28B	109.5
C12—C13—H13	119.7	C27—C28—H28C	109.5
C14—C13—H13	119.7	H28A—C28—H28C	109.5
C13—C14—C9	118.5 (2)	H28B—C28—H28C	109.5
C13—C14—C18	119.5 (2)	C27—C29—H29A	109.5
C9—C14—C18	122.01 (19)	C27—C29—H29B	109.5
C17—C15—C10	112.7 (2)	H29A—C29—H29B	109.5
C17—C15—C16	111.0 (3)	C27—C29—H29C	109.5
C10—C15—C16	109.8 (2)	H29A—C29—H29C	109.5
C17—C15—H15	107.7	H29B—C29—H29C	109.5
C10—C15—H15	107.7	C31—C30—C32	112.0 (3)
C16—C15—H15	107.7	C31—C30—C26	112.7 (2)
C15—C16—H16A	109.5	C32—C30—C26	110.6 (2)
C15—C16—H16B	109.5	C31—C30—H30	107.1
H16A—C16—H16B	109.5	C32—C30—H30	107.1
C15—C16—H16C	109.5	C26—C30—H30	107.1
H16A—C16—H16C	109.5	C30—C31—H31A	109.5
H16B—C16—H16C	109.5	C30—C31—H31B	109.5
C15—C17—H17A	109.5	H31A—C31—H31B	109.5
C15—C17—H17B	109.5	C30—C31—H31C	109.5
H17A—C17—H17B	109.5	H31A—C31—H31C	109.5
C15—C17—H17C	109.5	H31B—C31—H31C	109.5
H17A—C17—H17C	109.5	C30—C32—H32A	109.5
H17B—C17—H17C	109.5	C30—C32—H32B	109.5
C14—C18—C19	112.0 (2)	H32A—C32—H32B	109.5
C14—C18—C20	111.2 (2)	C30—C32—H32C	109.5
C19—C18—C20	111.0 (2)	H32A—C32—H32C	109.5
C14—C18—H18	107.5	H32B—C32—H32C	109.5
C3—N1—C1—C1i	−178.3 (2)	C11—C10—C15—C17	51.1 (3)
C3—N1—C1—C2	2.1 (3)	C9—C10—C15—C17	−130.1 (3)
C1—N1—C3—C4	71.8 (3)	C11—C10—C15—C16	−73.1 (3)
C1—N1—C3—C8	−112.1 (2)	C9—C10—C15—C16	105.6 (3)
C8—C3—C4—C5	2.0 (3)	C13—C14—C18—C19	−58.5 (3)
N1—C3—C4—C5	178.11 (18)	C9—C14—C18—C19	121.9 (2)
C3—C4—C5—C6	−1.0 (3)	C13—C14—C18—C20	66.3 (3)
C3—C4—C5—C9	177.89 (19)	C9—C14—C18—C20	−113.3 (2)
C4—C5—C6—C7	−0.1 (3)	C8—C7—C21—C22	−83.0 (3)
C9—C5—C6—C7	−179.03 (18)	C6—C7—C21—C22	96.9 (2)
C5—C6—C7—C8	0.2 (3)	C8—C7—C21—C26	98.1 (2)
C5—C6—C7—C21	−179.70 (18)	C6—C7—C21—C26	−82.0 (2)
C6—C7—C8—C3	0.8 (3)	C26—C21—C22—C23	1.5 (3)
C21—C7—C8—C3	−179.31 (18)	C7—C21—C22—C23	−177.34 (19)
C4—C3—C8—C7	−1.9 (3)	C26—C21—C22—C27	−179.36 (19)
N1—C3—C8—C7	−178.08 (18)	C7—C21—C22—C27	1.8 (3)
C6—C5—C9—C14	−89.4 (2)	C21—C22—C23—C24	−0.5 (3)
C4—C5—C9—C14	91.7 (2)	C27—C22—C23—C24	−179.6 (2)
C6—C5—C9—C10	89.2 (2)	C22—C23—C24—C25	−0.7 (4)
C4—C5—C9—C10	−89.7 (2)	C23—C24—C25—C26	0.7 (4)
C14—C9—C10—C11	0.3 (3)	C24—C25—C26—C21	0.4 (3)
C5—C9—C10—C11	−178.33 (18)	C24—C25—C26—C30	−177.4 (2)
C14—C9—C10—C15	−178.52 (19)	C22—C21—C26—C25	−1.5 (3)
C5—C9—C10—C15	2.9 (3)	C7—C21—C26—C25	177.40 (19)
C9—C10—C11—C12	−1.1 (3)	C22—C21—C26—C30	176.3 (2)
C15—C10—C11—C12	177.8 (2)	C7—C21—C26—C30	−4.8 (3)
C10—C11—C12—C13	0.6 (4)	C23—C22—C27—C29	−30.5 (3)
C11—C12—C13—C14	0.6 (4)	C21—C22—C27—C29	150.4 (2)
C12—C13—C14—C9	−1.3 (3)	C23—C22—C27—C28	94.8 (2)
C12—C13—C14—C18	179.0 (2)	C21—C22—C27—C28	−84.3 (2)
C10—C9—C14—C13	0.9 (3)	C25—C26—C30—C31	−57.7 (4)
C5—C9—C14—C13	179.50 (18)	C21—C26—C30—C31	124.6 (3)
C10—C9—C14—C18	−179.45 (18)	C25—C26—C30—C32	68.6 (3)
C5—C9—C14—C18	−0.8 (3)	C21—C26—C30—C32	−109.2 (3)