(Z)-N-{(E)-10-[(2,6-Diisopropyl-phen-yl)-imino]-9,10-dihydro-phenanthren-9-yl-idene}-2,6-dimethyl-aniline.

The title compound, C(34)H(34)N(2), adopts a Z,E configuration with respect to the N=C-C=N backbone, with an N-C-C-N torsion angle of 41.1 (4)° The dihedral angle between the benzene rings in the 9,10-dihydro-phenanthrene moiety is 18.0 (1)°.

Related literature

For the synthesis and applications of related α-diimines in catalysis and coordination chemistry, see: Li, Gomes et al. (2009 ▶); Li, Jeon et al. (2009 ▶); Gao et al. (2011 ▶); Bochkarev et al. (2010 ▶); Belzen et al. (1996 ▶). For standard bond distances, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C34H34N2

M = 470.63

Monoclinic,

a = 9.5495 (7) Å

b = 16.4294 (12) Å

c = 17.7237 (13) Å

β = 104.579 (1)°

V = 2691.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 185 K

0.23 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.985, T max = 0.990

14490 measured reflections

5304 independent reflections

4587 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.161

S = 1.27

5304 reflections

331 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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) global, I. DOI: 10.1107/S1600536812003790/lr2046sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812003790/lr2046Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812003790/lr2046Isup3.cml

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

C34H34N2	F(000) = 1008
Mr = 470.63	Dx = 1.162 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3054 reflections
a = 9.5495 (7) Å	θ = 2.4–26.0°
b = 16.4294 (12) Å	µ = 0.07 mm−1
c = 17.7237 (13) Å	T = 185 K
β = 104.579 (1)°	Block, red
V = 2691.2 (3) Å3	0.23 × 0.20 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	5304 independent reflections
Radiation source: fine-focus sealed tube	4587 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
phi and ω scan	θmax = 26.1°, θmin = 1.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→11
Tmin = 0.985, Tmax = 0.990	k = −20→20
14490 measured reflections	l = −21→21

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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.27	w = 1/[σ2(Fo2) + (0.0304P)2 + 2.1478P] where P = (Fo2 + 2Fc2)/3
5304 reflections	(Δ/σ)max < 0.001
331 parameters	Δρmax = 0.21 e Å−3
0 restraints	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	0.3180 (2)	0.67770 (13)	0.09099 (13)	0.0284 (5)
N2	0.5846 (2)	0.75349 (12)	0.18313 (12)	0.0242 (5)
C1	0.4448 (3)	0.64761 (15)	0.11007 (14)	0.0243 (5)
C2	0.4616 (3)	0.55816 (15)	0.11074 (14)	0.0252 (5)
C3	0.3482 (3)	0.50826 (16)	0.11938 (15)	0.0292 (6)
H3	0.2607	0.5315	0.1219	0.035*
C4	0.3650 (3)	0.42518 (17)	0.12425 (16)	0.0346 (7)
H4	0.2889	0.3923	0.1299	0.042*
C5	0.4951 (4)	0.39055 (17)	0.12071 (17)	0.0392 (7)
H5	0.5070	0.3344	0.1245	0.047*
C6	0.6079 (3)	0.43939 (17)	0.11159 (17)	0.0370 (7)
H6	0.6950	0.4155	0.1093	0.044*
C7	0.5933 (3)	0.52341 (16)	0.10582 (14)	0.0276 (6)
C8	0.7101 (3)	0.57685 (16)	0.09295 (14)	0.0268 (6)
C9	0.8246 (3)	0.54597 (18)	0.06549 (16)	0.0338 (6)
H9	0.8280	0.4906	0.0554	0.041*
C10	0.9324 (3)	0.59620 (19)	0.05315 (17)	0.0374 (7)
H10	1.0081	0.5743	0.0354	0.045*
C11	0.9286 (3)	0.6783 (2)	0.06693 (16)	0.0374 (7)
H11	1.0005	0.7121	0.0576	0.045*
C12	0.8174 (3)	0.71061 (18)	0.09474 (15)	0.0314 (6)
H12	0.8160	0.7661	0.1048	0.038*
C13	0.7073 (3)	0.66092 (16)	0.10781 (14)	0.0258 (6)
C14	0.5844 (3)	0.69431 (15)	0.13656 (14)	0.0232 (5)
C15	0.2838 (3)	0.76208 (16)	0.09064 (16)	0.0279 (6)
C16	0.2400 (3)	0.79411 (18)	0.15418 (17)	0.0359 (7)
C17	0.1844 (4)	0.8721 (2)	0.1478 (2)	0.0496 (9)
H17	0.1548	0.8944	0.1895	0.060*
C18	0.1717 (4)	0.9179 (2)	0.0808 (2)	0.0542 (9)
H18	0.1334	0.9702	0.0776	0.065*
C19	0.2160 (4)	0.88567 (18)	0.01948 (19)	0.0444 (8)
H19	0.2077	0.9167	−0.0253	0.053*
C20	0.2733 (3)	0.80749 (17)	0.02270 (16)	0.0322 (6)
C21	0.2522 (4)	0.7434 (2)	0.22597 (19)	0.0509 (9)
H21A	0.2089	0.7719	0.2617	0.076*
H21B	0.3524	0.7332	0.2504	0.076*
H21C	0.2030	0.6925	0.2118	0.076*
C22	0.3218 (4)	0.77238 (19)	−0.04485 (17)	0.0437 (8)
H22A	0.2704	0.7227	−0.0614	0.066*
H22B	0.4238	0.7615	−0.0291	0.066*
H22C	0.3022	0.8106	−0.0872	0.066*
C23	0.7117 (3)	0.79637 (16)	0.22119 (15)	0.0258 (6)
C24	0.8176 (3)	0.75988 (17)	0.28037 (15)	0.0293 (6)
C25	0.9359 (3)	0.8071 (2)	0.31794 (18)	0.0397 (7)
H25	1.0074	0.7840	0.3577	0.048*
C26	0.9493 (3)	0.88710 (19)	0.29748 (19)	0.0421 (8)
H26	1.0308	0.9169	0.3220	0.051*
C27	0.8415 (3)	0.92263 (18)	0.24066 (18)	0.0379 (7)
H27	0.8509	0.9768	0.2274	0.045*
C28	0.7196 (3)	0.87959 (17)	0.20282 (15)	0.0306 (6)
C29	0.5983 (4)	0.91871 (17)	0.14141 (17)	0.0383 (7)
H29	0.5096	0.8886	0.1413	0.046*
C30	0.6225 (5)	0.9105 (2)	0.06026 (18)	0.0586 (10)
H30A	0.7107	0.9376	0.0585	0.088*
H30B	0.5429	0.9349	0.0229	0.088*
H30C	0.6291	0.8540	0.0481	0.088*
C31	0.5708 (5)	1.0078 (2)	0.1589 (2)	0.0602 (10)
H31A	0.6528	1.0402	0.1556	0.090*
H31B	0.5563	1.0120	0.2104	0.090*
H31C	0.4862	1.0271	0.1216	0.090*
C32	0.8049 (3)	0.67254 (17)	0.30739 (16)	0.0349 (7)
H32	0.7180	0.6488	0.2728	0.042*
C33	0.9338 (4)	0.6197 (2)	0.3016 (2)	0.0543 (9)
H33A	0.9457	0.6221	0.2494	0.082*
H33B	0.9167	0.5644	0.3143	0.082*
H33C	1.0199	0.6395	0.3374	0.082*
C34	0.7840 (5)	0.6712 (2)	0.3902 (2)	0.0620 (11)
H34A	0.8684	0.6931	0.4258	0.093*
H34B	0.7692	0.6161	0.4047	0.093*
H34C	0.7011	0.7035	0.3921	0.093*

	U11	U22	U33	U12	U13	U23
N1	0.0223 (11)	0.0285 (12)	0.0348 (12)	−0.0014 (10)	0.0080 (10)	−0.0008 (10)
N2	0.0220 (11)	0.0227 (11)	0.0268 (11)	0.0005 (9)	0.0040 (9)	0.0001 (9)
C1	0.0245 (13)	0.0280 (13)	0.0216 (12)	−0.0009 (11)	0.0079 (11)	−0.0022 (10)
C2	0.0276 (14)	0.0259 (13)	0.0208 (12)	−0.0028 (11)	0.0037 (11)	−0.0034 (10)
C3	0.0276 (14)	0.0309 (15)	0.0286 (13)	−0.0015 (12)	0.0060 (12)	0.0030 (11)
C4	0.0404 (17)	0.0307 (15)	0.0335 (15)	−0.0092 (13)	0.0108 (13)	−0.0011 (12)
C5	0.0532 (19)	0.0202 (14)	0.0457 (17)	0.0000 (13)	0.0149 (16)	−0.0009 (12)
C6	0.0336 (16)	0.0306 (15)	0.0465 (17)	0.0071 (13)	0.0094 (14)	−0.0010 (13)
C7	0.0257 (13)	0.0328 (15)	0.0228 (12)	0.0030 (11)	0.0033 (11)	−0.0012 (11)
C8	0.0230 (13)	0.0343 (15)	0.0208 (12)	0.0017 (11)	0.0011 (11)	−0.0008 (11)
C9	0.0311 (15)	0.0378 (16)	0.0313 (14)	0.0078 (13)	0.0054 (12)	−0.0028 (12)
C10	0.0252 (14)	0.0514 (19)	0.0371 (16)	0.0052 (13)	0.0104 (13)	−0.0059 (14)
C11	0.0242 (14)	0.0549 (19)	0.0343 (15)	−0.0090 (14)	0.0095 (12)	−0.0029 (14)
C12	0.0270 (14)	0.0360 (15)	0.0306 (14)	−0.0057 (12)	0.0061 (12)	−0.0038 (12)
C13	0.0222 (13)	0.0337 (15)	0.0200 (12)	−0.0020 (11)	0.0025 (10)	−0.0010 (11)
C14	0.0236 (13)	0.0220 (12)	0.0234 (12)	0.0026 (10)	0.0049 (10)	0.0029 (10)
C15	0.0179 (12)	0.0255 (14)	0.0390 (15)	−0.0013 (10)	0.0048 (11)	−0.0042 (11)
C16	0.0280 (15)	0.0394 (17)	0.0421 (16)	−0.0012 (13)	0.0124 (13)	−0.0076 (13)
C17	0.048 (2)	0.047 (2)	0.059 (2)	0.0048 (16)	0.0225 (17)	−0.0158 (17)
C18	0.057 (2)	0.0331 (18)	0.071 (2)	0.0147 (16)	0.0117 (19)	−0.0088 (17)
C19	0.0490 (19)	0.0307 (16)	0.0497 (18)	0.0041 (14)	0.0054 (16)	0.0028 (14)
C20	0.0246 (14)	0.0329 (15)	0.0365 (15)	−0.0009 (12)	0.0030 (12)	−0.0052 (12)
C21	0.051 (2)	0.061 (2)	0.0476 (19)	0.0000 (17)	0.0258 (17)	−0.0034 (17)
C22	0.052 (2)	0.0426 (18)	0.0359 (16)	0.0019 (15)	0.0105 (15)	−0.0037 (13)
C23	0.0237 (13)	0.0288 (14)	0.0266 (13)	−0.0023 (11)	0.0097 (11)	−0.0050 (11)
C24	0.0242 (14)	0.0349 (15)	0.0288 (13)	0.0026 (12)	0.0068 (11)	−0.0052 (12)
C25	0.0236 (14)	0.0531 (19)	0.0388 (16)	0.0065 (14)	0.0015 (13)	−0.0102 (14)
C26	0.0279 (15)	0.0450 (18)	0.0525 (19)	−0.0115 (14)	0.0085 (14)	−0.0197 (15)
C27	0.0385 (17)	0.0306 (15)	0.0485 (17)	−0.0128 (13)	0.0184 (15)	−0.0076 (13)
C28	0.0333 (15)	0.0348 (15)	0.0255 (13)	−0.0027 (12)	0.0108 (12)	−0.0036 (11)
C29	0.0500 (19)	0.0285 (15)	0.0358 (15)	−0.0028 (14)	0.0098 (14)	0.0040 (12)
C30	0.085 (3)	0.051 (2)	0.0367 (17)	0.007 (2)	0.0093 (19)	0.0064 (15)
C31	0.081 (3)	0.045 (2)	0.050 (2)	0.0152 (19)	0.007 (2)	0.0005 (16)
C32	0.0347 (16)	0.0362 (16)	0.0306 (14)	0.0080 (13)	0.0024 (13)	0.0027 (12)
C33	0.058 (2)	0.047 (2)	0.058 (2)	0.0203 (18)	0.0152 (19)	0.0099 (17)
C34	0.089 (3)	0.052 (2)	0.054 (2)	0.007 (2)	0.033 (2)	0.0065 (17)

N1—C1	1.272 (3)	C19—H19	0.9300
N1—C15	1.424 (3)	C20—C22	1.503 (4)
N2—C14	1.275 (3)	C21—H21A	0.9600
N2—C23	1.418 (3)	C21—H21B	0.9600
C1—C2	1.478 (3)	C21—H21C	0.9600
C1—C14	1.507 (3)	C22—H22A	0.9600
C2—C3	1.397 (4)	C22—H22B	0.9600
C2—C7	1.404 (4)	C22—H22C	0.9600
C3—C4	1.374 (4)	C23—C24	1.396 (4)
C3—H3	0.9300	C23—C28	1.412 (4)
C4—C5	1.383 (4)	C24—C25	1.393 (4)
C4—H4	0.9300	C24—C32	1.527 (4)
C5—C6	1.384 (4)	C25—C26	1.379 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.389 (4)	C26—C27	1.376 (4)
C6—H6	0.9300	C26—H26	0.9300
C7—C8	1.481 (4)	C27—C28	1.383 (4)
C8—C9	1.399 (4)	C27—H27	0.9300
C8—C13	1.408 (4)	C28—C29	1.518 (4)
C9—C10	1.380 (4)	C29—C30	1.519 (4)
C9—H9	0.9300	C29—C31	1.532 (4)
C10—C11	1.373 (4)	C29—H29	0.9800
C10—H10	0.9300	C30—H30A	0.9600
C11—C12	1.384 (4)	C30—H30B	0.9600
C11—H11	0.9300	C30—H30C	0.9600
C12—C13	1.396 (4)	C31—H31A	0.9600
C12—H12	0.9300	C31—H31B	0.9600
C13—C14	1.496 (3)	C31—H31C	0.9600
C15—C20	1.398 (4)	C32—C34	1.530 (4)
C15—C16	1.399 (4)	C32—C33	1.531 (4)
C16—C17	1.380 (4)	C32—H32	0.9800
C16—C21	1.501 (4)	C33—H33A	0.9600
C17—C18	1.386 (5)	C33—H33B	0.9600
C17—H17	0.9300	C33—H33C	0.9600
C18—C19	1.369 (5)	C34—H34A	0.9600
C18—H18	0.9300	C34—H34B	0.9600
C19—C20	1.391 (4)	C34—H34C	0.9600
C1—N1—C15	125.5 (2)	H21A—C21—H21B	109.5
C14—N2—C23	123.3 (2)	C16—C21—H21C	109.5
N1—C1—C2	118.8 (2)	H21A—C21—H21C	109.5
N1—C1—C14	126.4 (2)	H21B—C21—H21C	109.5
C2—C1—C14	114.7 (2)	C20—C22—H22A	109.5
C3—C2—C7	120.0 (2)	C20—C22—H22B	109.5
C3—C2—C1	119.9 (2)	H22A—C22—H22B	109.5
C7—C2—C1	120.1 (2)	C20—C22—H22C	109.5
C4—C3—C2	120.6 (3)	H22A—C22—H22C	109.5
C4—C3—H3	119.7	H22B—C22—H22C	109.5
C2—C3—H3	119.7	C24—C23—C28	121.2 (2)
C3—C4—C5	119.8 (3)	C24—C23—N2	121.0 (2)
C3—C4—H4	120.1	C28—C23—N2	117.4 (2)
C5—C4—H4	120.1	C25—C24—C23	117.8 (3)
C4—C5—C6	120.1 (3)	C25—C24—C32	119.5 (3)
C4—C5—H5	120.0	C23—C24—C32	122.6 (2)
C6—C5—H5	120.0	C26—C25—C24	121.5 (3)
C5—C6—C7	121.2 (3)	C26—C25—H25	119.2
C5—C6—H6	119.4	C24—C25—H25	119.2
C7—C6—H6	119.4	C27—C26—C25	119.7 (3)
C6—C7—C2	118.3 (3)	C27—C26—H26	120.2
C6—C7—C8	122.4 (2)	C25—C26—H26	120.2
C2—C7—C8	119.3 (2)	C26—C27—C28	121.4 (3)
C9—C8—C13	118.3 (2)	C26—C27—H27	119.3
C9—C8—C7	121.5 (2)	C28—C27—H27	119.3
C13—C8—C7	120.2 (2)	C27—C28—C23	118.1 (3)
C10—C9—C8	121.2 (3)	C27—C28—C29	121.9 (3)
C10—C9—H9	119.4	C23—C28—C29	120.0 (2)
C8—C9—H9	119.4	C28—C29—C30	111.8 (3)
C11—C10—C9	120.3 (3)	C28—C29—C31	113.4 (3)
C11—C10—H10	119.8	C30—C29—C31	110.5 (3)
C9—C10—H10	119.8	C28—C29—H29	106.9
C10—C11—C12	119.8 (3)	C30—C29—H29	106.9
C10—C11—H11	120.1	C31—C29—H29	106.9
C12—C11—H11	120.1	C29—C30—H30A	109.5
C11—C12—C13	120.8 (3)	C29—C30—H30B	109.5
C11—C12—H12	119.6	H30A—C30—H30B	109.5
C13—C12—H12	119.6	C29—C30—H30C	109.5
C12—C13—C8	119.5 (2)	H30A—C30—H30C	109.5
C12—C13—C14	122.0 (2)	H30B—C30—H30C	109.5
C8—C13—C14	118.5 (2)	C29—C31—H31A	109.5
N2—C14—C13	128.8 (2)	C29—C31—H31B	109.5
N2—C14—C1	116.6 (2)	H31A—C31—H31B	109.5
C13—C14—C1	114.5 (2)	C29—C31—H31C	109.5
C20—C15—C16	121.4 (3)	H31A—C31—H31C	109.5
C20—C15—N1	119.3 (2)	H31B—C31—H31C	109.5
C16—C15—N1	118.5 (2)	C24—C32—C34	110.8 (2)
C17—C16—C15	118.1 (3)	C24—C32—C33	112.5 (3)
C17—C16—C21	122.0 (3)	C34—C32—C33	111.0 (3)
C15—C16—C21	119.9 (3)	C24—C32—H32	107.5
C16—C17—C18	121.5 (3)	C34—C32—H32	107.5
C16—C17—H17	119.2	C33—C32—H32	107.5
C18—C17—H17	119.2	C32—C33—H33A	109.5
C19—C18—C17	119.5 (3)	C32—C33—H33B	109.5
C19—C18—H18	120.2	H33A—C33—H33B	109.5
C17—C18—H18	120.2	C32—C33—H33C	109.5
C18—C19—C20	121.4 (3)	H33A—C33—H33C	109.5
C18—C19—H19	119.3	H33B—C33—H33C	109.5
C20—C19—H19	119.3	C32—C34—H34A	109.5
C19—C20—C15	118.0 (3)	C32—C34—H34B	109.5
C19—C20—C22	121.2 (3)	H34A—C34—H34B	109.5
C15—C20—C22	120.7 (3)	C32—C34—H34C	109.5
C16—C21—H21A	109.5	H34A—C34—H34C	109.5
C16—C21—H21B	109.5	H34B—C34—H34C	109.5
C15—N1—C1—C2	177.2 (2)	C2—C1—C14—C13	40.5 (3)
C15—N1—C1—C14	0.4 (4)	C1—N1—C15—C20	90.7 (3)
N1—C1—C2—C3	−23.6 (4)	C1—N1—C15—C16	−99.0 (3)
C14—C1—C2—C3	153.6 (2)	C20—C15—C16—C17	0.6 (4)
N1—C1—C2—C7	158.9 (2)	N1—C15—C16—C17	−169.5 (3)
C14—C1—C2—C7	−23.8 (3)	C20—C15—C16—C21	179.6 (3)
C7—C2—C3—C4	0.9 (4)	N1—C15—C16—C21	9.6 (4)
C1—C2—C3—C4	−176.5 (2)	C15—C16—C17—C18	0.0 (5)
C2—C3—C4—C5	0.1 (4)	C21—C16—C17—C18	−179.0 (3)
C3—C4—C5—C6	−0.6 (4)	C16—C17—C18—C19	−0.4 (5)
C4—C5—C6—C7	0.0 (5)	C17—C18—C19—C20	0.2 (5)
C5—C6—C7—C2	1.0 (4)	C18—C19—C20—C15	0.3 (5)
C5—C6—C7—C8	−177.5 (3)	C18—C19—C20—C22	−180.0 (3)
C3—C2—C7—C6	−1.5 (4)	C16—C15—C20—C19	−0.8 (4)
C1—C2—C7—C6	176.0 (2)	N1—C15—C20—C19	169.2 (3)
C3—C2—C7—C8	177.1 (2)	C16—C15—C20—C22	179.6 (3)
C1—C2—C7—C8	−5.4 (4)	N1—C15—C20—C22	−10.5 (4)
C6—C7—C8—C9	17.3 (4)	C14—N2—C23—C24	−70.3 (3)
C2—C7—C8—C9	−161.3 (2)	C14—N2—C23—C28	116.2 (3)
C6—C7—C8—C13	−163.2 (3)	C28—C23—C24—C25	−3.5 (4)
C2—C7—C8—C13	18.3 (4)	N2—C23—C24—C25	−176.7 (2)
C13—C8—C9—C10	0.0 (4)	C28—C23—C24—C32	173.6 (2)
C7—C8—C9—C10	179.6 (3)	N2—C23—C24—C32	0.5 (4)
C8—C9—C10—C11	−0.7 (4)	C23—C24—C25—C26	−0.4 (4)
C9—C10—C11—C12	1.2 (4)	C32—C24—C25—C26	−177.6 (3)
C10—C11—C12—C13	−1.1 (4)	C24—C25—C26—C27	2.4 (4)
C11—C12—C13—C8	0.4 (4)	C25—C26—C27—C28	−0.5 (4)
C11—C12—C13—C14	−179.0 (2)	C26—C27—C28—C23	−3.2 (4)
C9—C8—C13—C12	0.1 (4)	C26—C27—C28—C29	178.5 (3)
C7—C8—C13—C12	−179.4 (2)	C24—C23—C28—C27	5.3 (4)
C9—C8—C13—C14	179.5 (2)	N2—C23—C28—C27	178.7 (2)
C7—C8—C13—C14	−0.1 (3)	C24—C23—C28—C29	−176.4 (2)
C23—N2—C14—C13	−4.4 (4)	N2—C23—C28—C29	−3.0 (4)
C23—N2—C14—C1	171.4 (2)	C27—C28—C29—C30	89.9 (3)
C12—C13—C14—N2	−33.8 (4)	C23—C28—C29—C30	−88.4 (3)
C8—C13—C14—N2	146.8 (3)	C27—C28—C29—C31	−35.9 (4)
C12—C13—C14—C1	150.3 (2)	C23—C28—C29—C31	145.9 (3)
C8—C13—C14—C1	−29.0 (3)	C25—C24—C32—C34	65.4 (4)
N1—C1—C14—N2	41.1 (4)	C23—C24—C32—C34	−111.7 (3)
C2—C1—C14—N2	−135.9 (2)	C25—C24—C32—C33	−59.4 (3)
N1—C1—C14—C13	−142.5 (3)	C23—C24—C32—C33	123.5 (3)