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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2012 Feb 4;68(Pt 3):o607. doi: 10.1107/S1600536812003790

(Z)-N-{(E)-10-[(2,6-Diisopropyl­phen­yl)­imino]-9,10-dihydro­phenanthren-9-yl­idene}-2,6-dimethyl­aniline

Dongni Li a, Hongmei Yu a, Tianhua Yu a, Haiying Liang a, Tiemei Liu a,*
PMCID: PMC3295409  PMID: 22412520

Abstract

The title compound, C34H34N2, 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-dihydro­phenanthrene 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 ▶).graphic file with name e-68-0o607-scheme1.jpg

Experimental  

Crystal data  

  • C34H34N2

  • M r = 470.63

  • Monoclinic, Inline graphic

  • 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003790/lr2046sup1.cif

e-68-0o607-sup1.cif (33.9KB, cif)

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

e-68-0o607-Isup2.hkl (259.7KB, hkl)

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

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

Acknowledgments

We thank the Department of Jilin Province Technology, China (grant No. 201015186), for support.

supplementary crystallographic information

Comment

α-diimines and their metal complexes have been attracted considerable interest due to their applications in catalysis and coordination chemistry. (Li, Gomes et al., 2009; Li, Jeon et al., 2009; Gao et al., 2011; Bochkarev et al., 2010; Belzen et al., 1996). In recent years, we have been interested in the development of high-performance catalyst systems based on diimine ligands and therefore synthesized a series of bis-(arylimino)acenaphthene ligands. Herein, we report the preparation and crystal structure of new phenanthrenequinone-based diimine compound, (I).

The title molecule, Fig. 1, is present as the Z, E configurational isomer. The C1—C14 distance is 1.507 (3) Å, indicative of no conjugation between the two imine bonds or between the phenyl groups of the phenanthrene backbone. The dihedral angle between the benzene rings of the phenanthrene moiet is 18.0 (1)°. The torsion angle of N1—C1—C14—N2 is 41.1 (4)°. Both lengths and angles in the title compound are in normal ranges (Allen et al., 1987) and are comparable to those of the known phenanthrenequinone-based diimine compounds (Belzen et al., 1996).

Experimental

To a solution of 2,6-diisopropylaniline (1.08 g, 7.2 mmol) and Dabco (2.49 g, 21.6 mmol) in toluene (30 ml) was added dropwise 7.2 ml of the 1.0 M solution of TiCl4 in toluene over 30 min at 363 k, followed by addition of a suspension of (E)-10-(2,6-dimethylphenylimino)phenanthren-9(10H)-one (Gao et al., 2011) (1.5 g, 4.80 mmol) in 10 ml of toluene. The reaction mixture was heated to 413 k for 8 h. The precipitate was removed by hot filtration. The filtrate was evaporated in vacuo. The deep red crystalline solid was isolated by silica gel column chromatography (hexane/ethyl acetate, 8:1). (1.08 g, yield: 48%) 1H NMR (300 MHz, CDCl3, 298 K) δ (p.p.m.): 0.60 (d, JH—H= 9.0 Hz, 3.6H, CH(CH3)2), 0.80 (d, JH—H= 6.0 Hz, 3.6H, CH(CH3)2), 1.01 (d, JH—H = 6.0 Hz, 2.4H, CH(CH3)2), 1.17 (d, JH—H= 9.0 Hz, 2.4H, CH(CH3)2), 1.35 (s, 2.4H, CH3), 1.79 (m, 1.2H, CH(CH3)2), 2.06 (s, 3.6H, CH3), 2.83 (m, 0.8, CH(CH3)2), 6.65–7.01 (m, 8H), 7.38 (m, 1H), 7.52 (m, 1H), 7.66 (m, 1H), 7.93 (m, 2H), 8.43 (m, 1H). 13C NMR (75 MHz, CDCl3, 298 K) δ (p.p.m.): 17.42, 18.62, 22.75, 22.97, 23.63, 24.25, 27.55, 28.90, 122.66, 122.77, 123.16, 123.26, 123.54, 123.60, 124.31, 124.73, 125.17, 127.20, 127.33, 127.46, 127.57, 127.86, 128.01, 128.91, 129.18, 131.35, 131.45, 131.92, 132.06, 133.64, 134.20, 134.60, 135.35, 135.50, 135.73, 145.40, 149.13, 156.77, 158.01, 159.37, 159.94 p.p.m..

Refinement

The H atoms were positioned geometrically with C—H = 0.95 (aromatic carbon), 0.99 (methylene) and 0.98 (methyl) Å, and allowed to ride on their parent atoms with Uiso(H) = 1.2 (1.5 for methyl) Ueq(C).

Figures

Fig. 1.

Fig. 1.

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A view of the molecule of the title compound.. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

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
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Data collection

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
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Refinement

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
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, º)

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)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LR2046).

References

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Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812003790/lr2046sup1.cif

e-68-0o607-sup1.cif (33.9KB, cif)

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

e-68-0o607-Isup2.hkl (259.7KB, hkl)

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

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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