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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Aug 11;67(Pt 9):o2281. doi: 10.1107/S1600536811031254

N,N′-Bis[3,5-bis­(2,6-diisopropyl­phen­yl)phen­yl]butane-2,3-diimine

Tracy L Lohr a, Warren E Piers a, Masood Parvez a,*
PMCID: PMC3200583  PMID: 22058928

Abstract

The title mol­ecule, C64H80N2, lies on an inversion center wherein the central butane­diimine 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 mol­ecule, 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 ▶).graphic file with name e-67-o2281-scheme1.jpg

Experimental

Crystal data

  • C64H80N2

  • M r = 877.30

  • Triclinic, Inline graphic

  • 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.

Supplementary Material

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

e-67-o2281-sup1.cif (26.4KB, cif)

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

e-67-o2281-Isup2.hkl (269.1KB, hkl)

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

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

Acknowledgments

Funding was provided by the NSERC of Canada in the form of a Doctoral Scholarship for TLL, and by an Alberta Innovates Studentship to TLL.

supplementary crystallographic information

Comment

To meet the ever-growing demand for green and carbon neutral energy, water splitting for the generation of hydrogen fuel represents an appealing strategy. To do their part, chemists have been looking at the steps towards organometallic mono-nuclear water splitting. (Yang & Hall, 2010; Kee et al., 2011; Blakemore et al., 2010). Our group is currently exploring the usage of platinum to mediate this reaction in an effort to understand the fundamental steps of O—H and O—O bond activation. This research is directed at synthesizing and studying plausible intermediates (Pt—OH and Pt—H species) in order to determine what role they play in the water activation process. The title compound was synthesized as a ligand to stabilize and isolate these highly reactive monomeric species for further mechanistic study.

In the title compound (Fig. 1), the central butanediimine fragment (N═ C(Me)–C(Me)═N) is essentially planar (maximum deviation of C1 being 0.002 (2) Å). The benzene ring (C3–C8) lies at 70.88 (10)° with respect to the mean-plane of the butanediimine fragment. The dihedral angles between the benzene ring bonded to N1 and benzene rings C9–C14 and C21–C26 are 89.61 (6) and 82.77 (6)°, respectively. The molecular dimesions in the title compound agree very well with the corresponding molecular dimensions reported in a few closely related compounds (Ionkin & Marshall, 2004; Zou et al., 2008; Lohr et al., 2011).

Experimental

Synthesis of (ArN=C(Me)—C(Me)=NAr) (Ar = 3,5-bis(2,6-diisopropylphenyl)benzene): In air, 3,5-bis(2,6-diisopropylphenyl)aniline (0.190 g, 0.471 mmol) and 2,3-butadione (0.021 ml, 0.236 mmol) were dissolved in MeOH (35 ml). To this yellow solution were added 3 drops of formic acid and the mixture was stirred at room temperature and a bright yellow precipitate formed overnight. The mixture was stirred for 14 h, cooled, filtered, washed with cold MeOH (3 x 5 ml), and dried over an aspirator for 3 h. The title compound was isolated as a light yellow solid (0.183 g, 45%). X-ray quality crystals were obtained through slow cooling to 243 K in concentrated ethyl acetate.

Refinement

Though the H-atoms were visible in the difference electron density maps they were included at geometrically idealized positions with C—H = 0.95, 0.98 and 1.00 Å for aryl, methine and methyl type H-atoms, respectively. The H-atoms were assigned Uiso = 1.2 times Ueq(C).

Figures

Fig. 1.

Fig. 1.

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The title molecule with displacement ellipsoids plotted at 30% probability level (Farrugia, 1997). Primed atoms are related by the symmetry code (-x, -y+1, -z).

Crystal data

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
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Data collection

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
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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)] = 0.069 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
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Special details

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

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*
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Atomic displacement parameters (Å2)

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)
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Geometric parameters (Å, °)

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)
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Symmetry codes: (i) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5297).

References

  1. Blakemore, J. D., Schley, N. D., Balcells, D., Hull, J. F., Olack, G. W., Incarvito, C. D., Einstein, O., Brudwig, G. W. & Crabtree, R. H. (2010). J. Am. Chem. Soc. 132, 16017–16029. [DOI] [PubMed]
  2. Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426.
  3. Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
  4. Hooft, R. (1998). COLLECT Nonius BV, Delft, The Netherlands.
  5. Ionkin, A. S. & Marshall, W. J. (2004). J. Organomet. Chem. 689, 1057–1063.
  6. Kee, J. W., Tan, Y. Y., Swennenhuis, B. H. G., Bengali, A. A. & Fan, W. Y. (2011). Organometallics, 30, 2154–2159.
  7. Lohr, T. L., Piers, W. E. & Parvez, M. (2011). Acta Cryst E67, o2280. [DOI] [PMC free article] [PubMed]
  8. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  9. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
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  11. Zou, H., Hou, Y., Yong, X., Cen, Y. & Bao, F. (2008). Acta Cryst. E64, o567. [DOI] [PMC free article] [PubMed]

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/S1600536811031254/lh5297sup1.cif

e-67-o2281-sup1.cif (26.4KB, cif)

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

e-67-o2281-Isup2.hkl (269.1KB, hkl)

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