2,5-Bis{2,2-bis-[4-(dimethyl-amino)-phen-yl]ethen-yl}-N,N'-diphenyl-N,N'-dipropyl-benzene-1,4-diamine.

The title compound, C(60)H(68)N(6), was prepared by Horner olefination of a terephthaldialdehyde and a diaryl-methyl phospho-nate. There is one half-mol-ecule, located on an inversion centre, in the asymmetric unit. The dihedral angle between the plane of the vinyl-ene unit and the central ring is 36.79 (15)°, while those between the vinyl-ene unit and the lateral phenyl rings are 53.04 (10) and 53.74 (9)°.

Related literature

For conjugated oligomers with basic sites as sensing materials for polarity and cations, see: Detert & Sugiono (2004 ▶, 2005 ▶); Wilson & Bunz (2005 ▶); Zucchero et al. (2009 ▶). For typical synthetic approaches to larger stilbenoid dyes, see: Drefahl & Plötner (1961 ▶); Stalmach et al. (1996 ▶). For crystal structures of phenyl­ene­vinyl­ene oligomers, see: van Hutten et al. (1999 ▶); Detert et al. (2001 ▶). For optical properties of dyes which are highly sensitive towards environmental changes, see: Detert et al. (2001 ▶); Strehmel et al. (2003 ▶); Nemkovich et al. (2010 ▶). For the synthesis of the title compound, see: Schmitt (2005 ▶); Zheng et al. (2003 ▶).

Experimental

Crystal data

C60H68N6

M = 873.20

Monoclinic,

a = 20.485 (9) Å

b = 12.0782 (16) Å

c = 21.108 (9) Å

β = 107.60 (2)°

V = 4978 (3) Å3

Z = 4

Cu Kα radiation

μ = 0.52 mm−1

T = 193 K

0.50 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

4859 measured reflections

4720 independent reflections

3352 reflections with I > 2σ(I)

R int = 0.064

3 standard reflections every 60 min intensity decay: 2%

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.232

S = 1.09

4720 reflections

303 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100910X/bt5488sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681100910X/bt5488Isup2.hkl

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

C60H68N6	F(000) = 1880
Mr = 873.20	Dx = 1.165 Mg m−3
Monoclinic, C2/c	Melting point: 487 K
Hall symbol: -C 2yc	Cu Kα radiation, λ = 1.54178 Å
a = 20.485 (9) Å	Cell parameters from 25 reflections
b = 12.0782 (16) Å	θ = 25–42°
c = 21.108 (9) Å	µ = 0.52 mm−1
β = 107.60 (2)°	T = 193 K
V = 4978 (3) Å3	Block, orange
Z = 4	0.50 × 0.30 × 0.20 mm

Enraf–Nonius CAD-4 diffractometer	Rint = 0.064
Radiation source: rotating anode	θmax = 69.9°, θmin = 4.3°
graphite	h = 0→24
ω/2θ scans	k = −14→0
4859 measured reflections	l = −25→24
4720 independent reflections	3 standard reflections every 60 min
3352 reflections with I > 2σ(I)	intensity decay: 2%

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.1466P)2 + 0.3409P] where P = (Fo2 + 2Fc2)/3
4720 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. 1H-NMR (CDCl3, 400 MHz): δ (ppm) = 7.24 (s, 2H), 7.10 (t, 8H), 6.87 (d, 3J = 8.7 Hz, 4H), 6.83 (t, 4H), 6.78 (d, 3J = 8.2 Hz, 8H), 6.76 (s, 2H), 6.67 (d, 3J = 8.6 Hz, 4H), 6.50 (s, 2H), 6.48 (d, 3J = 8.7 Hz, 4H), 6.43 (d, 3J = 8.6 Hz, 4H), 2.89 (s, 24H). 13C-NMR (CDCl3, 75 MHz): δ (ppm) = 149.6, 149.3, 147.5, 143.3, 142.3, 136.9, 132.2, 131.0, 128.7, 121.8, 121.0, 120.4 , 112.0, 111.6, 40.4, 20.4, 11.5. UV-vis (CH2Cl2): λmax = 406 nm, ε = 33680 cm2/mmol.

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
C1	0.21619 (12)	0.6465 (2)	0.48219 (12)	0.0467 (6)
C2	0.28093 (12)	0.6668 (2)	0.47567 (12)	0.0483 (6)
H2	0.3025	0.6096	0.4584	0.058*
C3	0.18502 (12)	0.7339 (2)	0.50685 (12)	0.0462 (6)
C4	0.18219 (12)	0.5391 (2)	0.46690 (12)	0.0469 (6)
H4	0.1543	0.5189	0.4937	0.056*
C5	0.18481 (12)	0.4645 (2)	0.41993 (11)	0.0440 (5)
C6	0.21911 (11)	0.4822 (2)	0.36801 (11)	0.0430 (5)
C7	0.26348 (12)	0.4027 (2)	0.35679 (12)	0.0463 (6)
H7	0.2729	0.3386	0.3841	0.056*
C8	0.29436 (13)	0.4136 (2)	0.30741 (13)	0.0500 (6)
H8	0.3254	0.3583	0.3025	0.060*
C9	0.28079 (12)	0.5045 (2)	0.26460 (12)	0.0475 (6)
C10	0.23708 (13)	0.5856 (2)	0.27643 (13)	0.0485 (6)
H10	0.2276	0.6498	0.2492	0.058*
C11	0.20742 (13)	0.5744 (2)	0.32659 (12)	0.0490 (6)
H11	0.1781	0.6314	0.3331	0.059*
N12	0.30968 (12)	0.5151 (2)	0.21328 (11)	0.0596 (6)
C13	0.34078 (19)	0.4193 (3)	0.19338 (18)	0.0781 (10)
H13A	0.3765	0.3900	0.2318	0.117*
H13B	0.3611	0.4405	0.1587	0.117*
H13C	0.3058	0.3624	0.1761	0.117*
C14	0.28180 (17)	0.5965 (3)	0.16197 (16)	0.0688 (8)
H14A	0.2329	0.5822	0.1412	0.103*
H14B	0.3057	0.5919	0.1283	0.103*
H14C	0.2879	0.6707	0.1817	0.103*
C15	0.14780 (12)	0.3576 (2)	0.41640 (11)	0.0442 (5)
C16	0.15885 (13)	0.2878 (2)	0.47074 (12)	0.0498 (6)
H16	0.1926	0.3070	0.5111	0.060*
C17	0.12212 (14)	0.1909 (2)	0.46776 (14)	0.0549 (7)
H17	0.1316	0.1446	0.5059	0.066*
C18	0.07141 (12)	0.1598 (2)	0.40984 (14)	0.0510 (6)
C19	0.06118 (13)	0.2285 (2)	0.35475 (14)	0.0542 (6)
H19	0.0276	0.2093	0.3142	0.065*
C20	0.09921 (14)	0.3244 (2)	0.35803 (13)	0.0512 (6)
H20	0.0918	0.3686	0.3193	0.061*
N21	0.03150 (13)	0.0666 (2)	0.40884 (14)	0.0673 (7)
C22	−0.01593 (18)	0.0313 (3)	0.34656 (19)	0.0805 (10)
H22A	−0.0489	0.0907	0.3285	0.121*
H22B	−0.0404	−0.0349	0.3539	0.121*
H22C	0.0093	0.0140	0.3151	0.121*
C23	0.0580 (2)	−0.0200 (3)	0.4572 (2)	0.0881 (11)
H23A	0.1007	−0.0488	0.4518	0.132*
H23B	0.0243	−0.0799	0.4503	0.132*
H23C	0.0668	0.0102	0.5021	0.132*
N24	0.11885 (10)	0.7210 (2)	0.51472 (10)	0.0497 (5)
C25	0.06185 (12)	0.6998 (2)	0.46013 (12)	0.0486 (6)
C26	0.06600 (15)	0.7106 (3)	0.39625 (14)	0.0683 (9)
H26	0.1082	0.7313	0.3897	0.082*
C27	0.0099 (2)	0.6919 (5)	0.34216 (18)	0.1160 (19)
H27	0.0141	0.6985	0.2987	0.139*
C28	−0.0521 (2)	0.6637 (5)	0.3498 (2)	0.124 (2)
H28	−0.0910	0.6514	0.3122	0.149*
C29	−0.05672 (18)	0.6539 (4)	0.4124 (2)	0.0959 (14)
H29	−0.0996	0.6355	0.4183	0.115*
C30	−0.00108 (14)	0.6698 (3)	0.46759 (16)	0.0609 (7)
H30	−0.0055	0.6604	0.5108	0.073*
C31	0.11212 (13)	0.7389 (2)	0.58080 (13)	0.0540 (6)
H31A	0.0648	0.7633	0.5765	0.065*
H31B	0.1438	0.7987	0.6033	0.065*
C32	0.1277 (2)	0.6363 (4)	0.62248 (18)	0.0875 (12)
H32A	0.1751	0.6121	0.6271	0.105*
H32B	0.0962	0.5764	0.5999	0.105*
C33	0.1201 (2)	0.6556 (4)	0.69168 (17)	0.0960 (14)
H33A	0.1442	0.7236	0.7107	0.144*
H33B	0.1398	0.5927	0.7205	0.144*
H33C	0.0715	0.6627	0.6881	0.144*

	U11	U22	U33	U12	U13	U23
C1	0.0514 (12)	0.0491 (14)	0.0409 (12)	−0.0079 (10)	0.0160 (10)	−0.0105 (11)
C2	0.0514 (13)	0.0504 (15)	0.0440 (13)	−0.0024 (10)	0.0160 (10)	−0.0127 (11)
C3	0.0485 (12)	0.0505 (15)	0.0417 (12)	−0.0045 (10)	0.0167 (9)	−0.0093 (11)
C4	0.0519 (12)	0.0476 (14)	0.0434 (12)	−0.0059 (10)	0.0179 (10)	−0.0065 (11)
C5	0.0476 (11)	0.0452 (13)	0.0386 (12)	−0.0045 (10)	0.0123 (9)	−0.0020 (10)
C6	0.0475 (11)	0.0417 (13)	0.0393 (12)	−0.0044 (9)	0.0125 (9)	−0.0072 (10)
C7	0.0540 (13)	0.0385 (13)	0.0461 (13)	0.0005 (10)	0.0147 (10)	−0.0024 (10)
C8	0.0531 (13)	0.0461 (14)	0.0518 (14)	0.0028 (10)	0.0172 (11)	−0.0049 (11)
C9	0.0482 (12)	0.0469 (14)	0.0481 (13)	−0.0073 (10)	0.0154 (10)	−0.0057 (11)
C10	0.0548 (13)	0.0418 (14)	0.0499 (14)	−0.0016 (10)	0.0173 (11)	0.0023 (11)
C11	0.0542 (13)	0.0445 (14)	0.0483 (14)	0.0006 (10)	0.0155 (10)	−0.0051 (11)
N12	0.0667 (13)	0.0645 (16)	0.0563 (13)	0.0005 (11)	0.0316 (11)	0.0015 (12)
C13	0.089 (2)	0.089 (3)	0.075 (2)	0.0114 (19)	0.0523 (18)	0.0008 (19)
C14	0.0745 (18)	0.078 (2)	0.0602 (17)	−0.0070 (16)	0.0301 (14)	0.0106 (16)
C15	0.0479 (11)	0.0475 (14)	0.0386 (12)	−0.0022 (10)	0.0153 (9)	−0.0041 (10)
C16	0.0515 (13)	0.0520 (15)	0.0428 (13)	−0.0047 (11)	0.0094 (10)	−0.0026 (11)
C17	0.0586 (14)	0.0541 (16)	0.0501 (14)	−0.0031 (12)	0.0134 (11)	0.0099 (12)
C18	0.0475 (12)	0.0437 (14)	0.0620 (16)	0.0002 (10)	0.0168 (11)	−0.0017 (12)
C19	0.0531 (13)	0.0499 (16)	0.0526 (14)	−0.0022 (11)	0.0054 (11)	−0.0061 (12)
C20	0.0605 (14)	0.0484 (15)	0.0411 (13)	−0.0038 (11)	0.0098 (10)	−0.0009 (11)
N21	0.0619 (13)	0.0475 (14)	0.0880 (18)	−0.0083 (10)	0.0162 (12)	0.0049 (13)
C22	0.0738 (19)	0.059 (2)	0.103 (3)	−0.0172 (16)	0.0191 (18)	−0.0126 (19)
C23	0.101 (3)	0.054 (2)	0.113 (3)	−0.0063 (18)	0.037 (2)	0.015 (2)
N24	0.0468 (11)	0.0617 (14)	0.0425 (11)	−0.0074 (9)	0.0164 (8)	−0.0121 (10)
C25	0.0510 (13)	0.0464 (14)	0.0479 (14)	−0.0044 (10)	0.0142 (10)	−0.0128 (11)
C26	0.0606 (16)	0.097 (3)	0.0457 (15)	0.0038 (16)	0.0140 (12)	−0.0092 (16)
C27	0.086 (3)	0.207 (6)	0.0492 (19)	0.018 (3)	0.0109 (17)	−0.029 (3)
C28	0.064 (2)	0.198 (6)	0.089 (3)	0.005 (3)	−0.0083 (19)	−0.064 (3)
C29	0.0549 (17)	0.122 (4)	0.103 (3)	−0.0181 (19)	0.0137 (18)	−0.048 (3)
C30	0.0520 (14)	0.0620 (18)	0.0696 (18)	−0.0091 (12)	0.0199 (13)	−0.0150 (14)
C31	0.0545 (13)	0.0617 (17)	0.0475 (14)	−0.0002 (12)	0.0179 (10)	−0.0085 (13)
C32	0.099 (3)	0.099 (3)	0.075 (2)	0.044 (2)	0.0414 (19)	0.023 (2)
C33	0.089 (2)	0.144 (4)	0.061 (2)	0.044 (2)	0.0324 (17)	0.035 (2)

C1—C2	1.396 (3)	C18—N21	1.387 (3)
C1—C3	1.412 (3)	C18—C19	1.392 (4)
C1—C4	1.461 (4)	C19—C20	1.386 (4)
C2—C3i	1.380 (4)	C19—H19	0.9500
C2—H2	0.9500	C20—H20	0.9500
C3—C2i	1.380 (4)	N21—C22	1.443 (4)
C3—N24	1.423 (3)	N21—C23	1.447 (4)
C4—C5	1.353 (3)	C22—H22A	0.9800
C4—H4	0.9500	C22—H22B	0.9800
C5—C6	1.485 (3)	C22—H22C	0.9800
C5—C15	1.487 (3)	C23—H23A	0.9800
C6—C7	1.391 (3)	C23—H23B	0.9800
C6—C11	1.391 (4)	C23—H23C	0.9800
C7—C8	1.380 (4)	N24—C25	1.394 (3)
C7—H7	0.9500	N24—C31	1.459 (3)
C8—C9	1.395 (4)	C25—C26	1.383 (4)
C8—H8	0.9500	C25—C30	1.393 (4)
C9—N12	1.388 (3)	C26—C27	1.372 (5)
C9—C10	1.399 (4)	C26—H26	0.9500
C10—C11	1.377 (4)	C27—C28	1.371 (7)
C10—H10	0.9500	C27—H27	0.9500
C11—H11	0.9500	C28—C29	1.359 (6)
N12—C13	1.443 (4)	C28—H28	0.9500
N12—C14	1.447 (4)	C29—C30	1.374 (4)
C13—H13A	0.9800	C29—H29	0.9500
C13—H13B	0.9800	C30—H30	0.9500
C13—H13C	0.9800	C31—C32	1.497 (5)
C14—H14A	0.9800	C31—H31A	0.9900
C14—H14B	0.9800	C31—H31B	0.9900
C14—H14C	0.9800	C32—C33	1.533 (5)
C15—C16	1.386 (4)	C32—H32A	0.9900
C15—C20	1.389 (3)	C32—H32B	0.9900
C16—C17	1.382 (4)	C33—H33A	0.9800
C16—H16	0.9500	C33—H33B	0.9800
C17—C18	1.395 (4)	C33—H33C	0.9800
C17—H17	0.9500
C2—C1—C3	117.0 (2)	C20—C19—C18	121.1 (2)
C2—C1—C4	122.5 (2)	C20—C19—H19	119.5
C3—C1—C4	120.4 (2)	C18—C19—H19	119.5
C3i—C2—C1	123.0 (2)	C19—C20—C15	121.8 (2)
C3i—C2—H2	118.5	C19—C20—H20	119.1
C1—C2—H2	118.5	C15—C20—H20	119.1
C2i—C3—C1	120.0 (2)	C18—N21—C22	119.0 (3)
C2i—C3—N24	119.1 (2)	C18—N21—C23	118.8 (3)
C1—C3—N24	120.9 (2)	C22—N21—C23	115.7 (3)
C5—C4—C1	129.1 (2)	N21—C22—H22A	109.5
C5—C4—H4	115.4	N21—C22—H22B	109.5
C1—C4—H4	115.4	H22A—C22—H22B	109.5
C4—C5—C6	125.2 (2)	N21—C22—H22C	109.5
C4—C5—C15	118.8 (2)	H22A—C22—H22C	109.5
C6—C5—C15	115.8 (2)	H22B—C22—H22C	109.5
C7—C6—C11	116.3 (2)	N21—C23—H23A	109.5
C7—C6—C5	120.3 (2)	N21—C23—H23B	109.5
C11—C6—C5	123.3 (2)	H23A—C23—H23B	109.5
C8—C7—C6	122.3 (2)	N21—C23—H23C	109.5
C8—C7—H7	118.8	H23A—C23—H23C	109.5
C6—C7—H7	118.8	H23B—C23—H23C	109.5
C7—C8—C9	121.2 (2)	C25—N24—C3	120.86 (19)
C7—C8—H8	119.4	C25—N24—C31	121.3 (2)
C9—C8—H8	119.4	C3—N24—C31	117.7 (2)
N12—C9—C8	121.9 (2)	C26—C25—C30	117.8 (3)
N12—C9—C10	121.4 (2)	C26—C25—N24	120.4 (2)
C8—C9—C10	116.6 (2)	C30—C25—N24	121.8 (2)
C11—C10—C9	121.6 (2)	C27—C26—C25	120.9 (3)
C11—C10—H10	119.2	C27—C26—H26	119.6
C9—C10—H10	119.2	C25—C26—H26	119.6
C10—C11—C6	122.0 (2)	C28—C27—C26	121.1 (4)
C10—C11—H11	119.0	C28—C27—H27	119.5
C6—C11—H11	119.0	C26—C27—H27	119.5
C9—N12—C13	118.9 (2)	C29—C28—C27	118.4 (3)
C9—N12—C14	118.8 (2)	C29—C28—H28	120.8
C13—N12—C14	115.9 (2)	C27—C28—H28	120.8
N12—C13—H13A	109.5	C28—C29—C30	121.9 (4)
N12—C13—H13B	109.5	C28—C29—H29	119.1
H13A—C13—H13B	109.5	C30—C29—H29	119.1
N12—C13—H13C	109.5	C29—C30—C25	120.0 (3)
H13A—C13—H13C	109.5	C29—C30—H30	120.0
H13B—C13—H13C	109.5	C25—C30—H30	120.0
N12—C14—H14A	109.5	N24—C31—C32	112.0 (3)
N12—C14—H14B	109.5	N24—C31—H31A	109.2
H14A—C14—H14B	109.5	C32—C31—H31A	109.2
N12—C14—H14C	109.5	N24—C31—H31B	109.2
H14A—C14—H14C	109.5	C32—C31—H31B	109.2
H14B—C14—H14C	109.5	H31A—C31—H31B	107.9
C16—C15—C20	116.8 (2)	C31—C32—C33	111.7 (3)
C16—C15—C5	122.3 (2)	C31—C32—H32A	109.3
C20—C15—C5	120.9 (2)	C33—C32—H32A	109.3
C17—C16—C15	121.8 (2)	C31—C32—H32B	109.3
C17—C16—H16	119.1	C33—C32—H32B	109.3
C15—C16—H16	119.1	H32A—C32—H32B	107.9
C16—C17—C18	121.3 (2)	C32—C33—H33A	109.5
C16—C17—H17	119.4	C32—C33—H33B	109.5
C18—C17—H17	119.4	H33A—C33—H33B	109.5
N21—C18—C19	122.1 (3)	C32—C33—H33C	109.5
N21—C18—C17	120.7 (3)	H33A—C33—H33C	109.5
C19—C18—C17	117.1 (2)	H33B—C33—H33C	109.5
C3—C1—C2—C3i	1.1 (4)	C5—C15—C16—C17	177.2 (2)
C4—C1—C2—C3i	−176.6 (2)	C15—C16—C17—C18	−0.9 (4)
C2—C1—C3—C2i	−1.1 (4)	C16—C17—C18—N21	−175.3 (3)
C4—C1—C3—C2i	176.7 (2)	C16—C17—C18—C19	2.1 (4)
C2—C1—C3—N24	179.6 (2)	N21—C18—C19—C20	176.4 (3)
C4—C1—C3—N24	−2.6 (4)	C17—C18—C19—C20	−1.0 (4)
C2—C1—C4—C5	−33.7 (4)	C18—C19—C20—C15	−1.6 (4)
C3—C1—C4—C5	148.6 (3)	C16—C15—C20—C19	2.8 (4)
C1—C4—C5—C6	−6.4 (4)	C5—C15—C20—C19	−176.0 (2)
C1—C4—C5—C15	177.1 (2)	C19—C18—N21—C22	8.5 (4)
C4—C5—C6—C7	131.4 (3)	C17—C18—N21—C22	−174.2 (3)
C15—C5—C6—C7	−52.0 (3)	C19—C18—N21—C23	159.1 (3)
C4—C5—C6—C11	−51.3 (3)	C17—C18—N21—C23	−23.6 (4)
C15—C5—C6—C11	125.4 (3)	C2i—C3—N24—C25	118.7 (3)
C11—C6—C7—C8	−0.1 (3)	C1—C3—N24—C25	−61.9 (4)
C5—C6—C7—C8	177.4 (2)	C2i—C3—N24—C31	−56.8 (3)
C6—C7—C8—C9	−1.9 (4)	C1—C3—N24—C31	122.5 (3)
C7—C8—C9—N12	−177.9 (2)	C3—N24—C25—C26	−11.8 (4)
C7—C8—C9—C10	2.9 (4)	C31—N24—C25—C26	163.6 (3)
N12—C9—C10—C11	178.9 (2)	C3—N24—C25—C30	169.8 (3)
C8—C9—C10—C11	−1.9 (4)	C31—N24—C25—C30	−14.8 (4)
C9—C10—C11—C6	−0.1 (4)	C30—C25—C26—C27	−0.3 (6)
C7—C6—C11—C10	1.2 (3)	N24—C25—C26—C27	−178.8 (4)
C5—C6—C11—C10	−176.3 (2)	C25—C26—C27—C28	1.1 (8)
C8—C9—N12—C13	15.2 (4)	C26—C27—C28—C29	−0.5 (9)
C10—C9—N12—C13	−165.6 (3)	C27—C28—C29—C30	−0.9 (9)
C8—C9—N12—C14	165.9 (3)	C28—C29—C30—C25	1.7 (7)
C10—C9—N12—C14	−14.9 (4)	C26—C25—C30—C29	−1.1 (5)
C4—C5—C15—C16	−55.0 (3)	N24—C25—C30—C29	177.4 (3)
C6—C5—C15—C16	128.2 (3)	C25—N24—C31—C32	98.4 (3)
C4—C5—C15—C20	123.8 (3)	C3—N24—C31—C32	−86.1 (3)
C6—C5—C15—C20	−53.0 (3)	N24—C31—C32—C33	−179.7 (3)
C20—C15—C16—C17	−1.6 (4)