2-(2,6-Diiso­propyl­phenyl­amino)-4-(2,6-diiso­propyl­phenyl­imino)-2-pentene toluene hemisolvate at 150 K

Bailey, P.J.; Liddle, S.T.; Parsons, S.

doi:10.1107/S1600536801009163

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2-(2,6-Diisopropylphenylamino)-4-(2,6-diisopropylphenylimino)-2-pentene toluene hemisolvate at 150 K

P. J. Bailey, S. T. Liddle and S. Parsons

The title compound 2-(2,6-diisopropylphenylamino)-4-(2,6-diisopropylphenylimino)pent-2-ene crystallizes as a toluene solvate, C₂₉H₄₂N₂·0.5C₇H₈; the observed bond lengths are consistent with delocalization of the imino and alkene double bonds across the N-C-C-C-N backbone.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801009163/cf6079sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536801009163/cf6079Isup2.hkl Contains datablock I

CCDC reference: 170790

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.060
wR factor = 0.141
Data-to-parameter ratio = 18.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level A:



PLAT_601  Alert A Structure Contains Solvent Accessible VOIDS of     494.00 A   3

Author response: Structure contains highly disordered toluene solvent molecules. These were treated by the SQUEEZE procedure of PLATON.

General Notes



FORMU_01  There is a discrepancy between the atom counts in the
          _chemical_formula_sum and the formula from the _atom_site* data.
          Atom count from _chemical_formula_sum:C32.5 H46 N2
          Atom count from the _atom_site data:  C29 H42 N2

CELLZ_01
         From the CIF: _cell_formula_units_Z    8
         From the CIF: _chemical_formula_sum  C32.5 H46 N2
         TEST: Compare cell contents of formula and atom_site data

         atom    Z*formula  cif sites diff
         C        260.00    232.00   28.00
         H        368.00    336.00   32.00
         N         16.00     16.00    0.00
          Difference between formula and atom_site contents detected.
          ALERT: Large difference may be due to a
          symmetry error - see SYMMG tests

CHEMW_03
         From the CIF: _cell_formula_units_Z                    8
         From the CIF: _chemical_formula_weight           464.71
         TEST: Calculate formula weight from _atom_site_*
         atom     mass    num     sum
         C        12.01   29.00  348.32
         H         1.01   42.00   42.34
         N        14.01    2.00   28.01
         Calculated formula weight              418.67
          ALERT: The ratio of given/expected molecular weight as calculated
          from the _atom_site* data lies outside
          the range 0.90 <> 1.10


 1 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

β-Diketimine ligands such as the title compound, (I), are proving to be versatile ligands in the monoanionic form for early transition metals in olefin polymerization (Budzelaar et al., 1998). Recently, we have been interested in the application of (I) for olefin polymerization by nitrogen-ligated organomagnesium species (Bailey et al., 2000). However, whilst there are now many examples of this ligand in the deprotonated monoanionc form as chelates, there are no examples to date of the free protonated parent ligand (I) itself. We report here the crystal structure of (I), which was synthesized via a standard procedure of acid-catalysed condensation of 2,4-pentanedione and 2,6-diisopropylaniline (Parks & Holm, 1968).

The crystal structure is composed of discrete molecules of (I) (Fig. 1) exhibiting no significant intermolecular contacts. The N—C [N1—C2 1.326 (2) and N2—C4 1.327 (2) Å] and C—C [C2—C3 1.398 (2) and C3—C4 1.401 (2) Å] bond lengths of the N—C—C—C—N backbone are in the range associated with aromatic N—C and C—C bonds (Allen et al., 1992). Variation between the N—C (N1—C2 and N2—C4) and C—C (C2—C3 and C3—C4) bonds are statistically insignificant. Compound (I) thus crystallizes as a mixture of the two possible imine–enamine tautomers (see Scheme); inspection of the difference map around C3 gives no evidence to suggest the presence of the third tautomer. As a consequence, the amine proton is disordered in 50:50% occupancy over both N1 and N2 with bond lengths of 0.90 (3) and 0.89 (3) Å, respectively.

The two backbone methyl groups (C1 and C5) adopt a syn orientation; this is surprising as an anti conformation would lead to a less congested conformer. It is likely that small steric, electronic and entropic factors, or crystal-packing forces, are responsible for this. The two phenyl rings adopt a synperiplanar arrangement in order to minimize steric crowding.

Experimental top

Compound (I) was synthesized by acid-catalysed condensation of 2,4-pentanedione and 2,6-diisopropylaniline in ethanol (Parks & Holm, 1968). Crystals were obtained from a saturated solution in toluene at 243 K.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. A view of (I) with the atom-numbering scheme. Displacement ellipsoids are at the 30% probability level.

2-(2,6-Diisopropylphenylamino)-4-(2,6-diisopropylphenylimino)-2-pentene top

Crystal data top

C₂₉H₄₂N₂·0.5C₇H₈	F(000) = 2040
M_r = 464.71	D_x = 1.020 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 26.655 (5) Å	Cell parameters from 10829 reflections
b = 18.004 (3) Å	θ = 2.2–26.4°
c = 12.623 (2) Å	µ = 0.06 mm⁻¹
β = 91.972 (3)°	T = 150 K
V = 6054.0 (19) Å³	Block, colourless
Z = 8	0.19 × 0.16 × 0.07 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5322 independent reflections
Radiation source: fine-focus sealed tube	4677 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −31→31
T_min = 0.989, T_max = 0.996	k = −21→21
21824 measured reflections	l = −14→14

Refinement top

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0507P)² + 4.1159P] where P = (F_o² + 2F_c²)/3
5322 reflections	(Δ/σ)_max < 0.001
296 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₉H₄₂N₂·0.5C₇H₈	V = 6054.0 (19) Å³
M_r = 464.71	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 26.655 (5) Å	µ = 0.06 mm⁻¹
b = 18.004 (3) Å	T = 150 K
c = 12.623 (2) Å	0.19 × 0.16 × 0.07 mm
β = 91.972 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5322 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	4677 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.996	R_int = 0.025
21824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.19 e Å⁻³
5322 reflections	Δρ_min = −0.17 e Å⁻³
296 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.45282 (6)	0.19078 (11)	0.45141 (14)	0.0431 (4)
H1A	0.4479	0.1407	0.4797	0.065*
H1B	0.4432	0.2276	0.5042	0.065*
H1C	0.4882	0.1976	0.4351	0.065*
C2	0.42081 (6)	0.20054 (8)	0.35211 (12)	0.0294 (4)
C3	0.36959 (6)	0.21714 (9)	0.35133 (12)	0.0315 (4)
H3	0.3554	0.2320	0.2846	0.038*
C4	0.33599 (6)	0.21517 (9)	0.43424 (12)	0.0301 (4)
C5	0.34609 (7)	0.17537 (11)	0.53763 (14)	0.0470 (5)
H5A	0.3672	0.2066	0.5845	0.070*
H5B	0.3634	0.1284	0.5243	0.070*
H5C	0.3142	0.1652	0.5713	0.070*
N1	0.44584 (5)	0.19537 (8)	0.26339 (11)	0.0333 (3)
H1N	0.4794 (12)	0.1932 (18)	0.259 (3)	0.040*	0.50
C6	0.42228 (6)	0.19119 (10)	0.16055 (13)	0.0370 (4)
C7	0.41329 (7)	0.12038 (12)	0.11755 (15)	0.0488 (5)
C8	0.39627 (8)	0.11616 (15)	0.01214 (18)	0.0647 (7)
H8	0.3897	0.0689	−0.0187	0.078*
C9	0.38884 (8)	0.17889 (17)	−0.04818 (17)	0.0686 (7)
H9	0.3781	0.1747	−0.1205	0.082*
C10	0.39694 (7)	0.24739 (15)	−0.00415 (16)	0.0596 (6)
H10	0.3911	0.2904	−0.0464	0.071*
C11	0.41347 (6)	0.25570 (11)	0.10105 (14)	0.0430 (4)
C12	0.42287 (7)	0.33206 (11)	0.14694 (16)	0.0492 (5)
H12	0.4262	0.3265	0.2257	0.059*
C13	0.37920 (9)	0.38491 (14)	0.1235 (2)	0.0780 (7)
H13A	0.3852	0.4319	0.1611	0.117*
H13B	0.3480	0.3625	0.1473	0.117*
H13C	0.3763	0.3944	0.0471	0.117*
C14	0.47210 (9)	0.36467 (14)	0.1094 (2)	0.0723 (7)
H14A	0.4777	0.4134	0.1424	0.108*
H14B	0.4703	0.3702	0.0321	0.108*
H14C	0.4999	0.3314	0.1297	0.108*
C15	0.42146 (9)	0.05100 (12)	0.1828 (2)	0.0661 (6)
H15	0.4404	0.0655	0.2493	0.079*
C16	0.45263 (12)	−0.00658 (16)	0.1264 (3)	0.0980 (10)
H16A	0.4580	−0.0498	0.1727	0.147*
H16B	0.4851	0.0150	0.1093	0.147*
H16C	0.4348	−0.0221	0.0608	0.147*
C17	0.37154 (12)	0.01708 (17)	0.2146 (3)	0.1102 (11)
H17A	0.3780	−0.0285	0.2552	0.165*
H17B	0.3511	0.0054	0.1508	0.165*
H17C	0.3536	0.0526	0.2583	0.165*
N2	0.29097 (5)	0.24651 (8)	0.42564 (10)	0.0319 (3)
H2N	0.2670 (13)	0.243 (2)	0.473 (3)	0.038*	0.50
C18	0.27649 (6)	0.29483 (9)	0.34030 (12)	0.0323 (4)
C19	0.25237 (6)	0.26592 (10)	0.24923 (13)	0.0376 (4)
C20	0.23346 (6)	0.31551 (12)	0.17346 (14)	0.0461 (5)
H20	0.2169	0.2969	0.1111	0.055*
C21	0.23820 (7)	0.39072 (12)	0.18709 (15)	0.0508 (5)
H21	0.2244	0.4238	0.1352	0.061*
C22	0.26304 (7)	0.41825 (11)	0.27607 (16)	0.0487 (5)
H22	0.2666	0.4704	0.2844	0.058*
C23	0.28308 (6)	0.37118 (10)	0.35411 (14)	0.0400 (4)
C24	0.31120 (8)	0.40243 (11)	0.45052 (17)	0.0558 (5)
H24	0.3187	0.3599	0.4995	0.067*
C25	0.36144 (11)	0.4357 (2)	0.4207 (3)	0.1203 (14)
H25A	0.3803	0.4506	0.4852	0.180*
H25B	0.3555	0.4792	0.3754	0.180*
H25C	0.3807	0.3986	0.3824	0.180*
C26	0.28106 (10)	0.45799 (14)	0.51090 (19)	0.0734 (7)
H26A	0.2999	0.4728	0.5755	0.110*
H26B	0.2491	0.4355	0.5300	0.110*
H26C	0.2745	0.5018	0.4665	0.110*
C27	0.24576 (7)	0.18283 (11)	0.23286 (14)	0.0454 (5)
H27	0.2665	0.1569	0.2891	0.054*
C28	0.26451 (10)	0.15802 (14)	0.12547 (19)	0.0735 (7)
H28A	0.2422	0.1775	0.0688	0.110*
H28B	0.2648	0.1036	0.1222	0.110*
H28C	0.2986	0.1770	0.1165	0.110*
C29	0.19131 (8)	0.16009 (13)	0.24554 (17)	0.0601 (6)
H29A	0.1883	0.1060	0.2388	0.090*
H29B	0.1702	0.1841	0.1904	0.090*
H29C	0.1804	0.1755	0.3155	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0313 (9)	0.0593 (12)	0.0388 (10)	0.0017 (8)	0.0046 (7)	0.0116 (8)
C2	0.0290 (8)	0.0274 (8)	0.0323 (9)	−0.0009 (6)	0.0066 (6)	0.0018 (6)
C3	0.0308 (8)	0.0363 (9)	0.0275 (8)	0.0015 (7)	0.0024 (6)	0.0034 (7)
C4	0.0282 (8)	0.0320 (8)	0.0304 (8)	−0.0002 (6)	0.0038 (6)	−0.0001 (7)
C5	0.0359 (9)	0.0662 (13)	0.0394 (10)	0.0058 (9)	0.0097 (8)	0.0168 (9)
N1	0.0239 (7)	0.0404 (8)	0.0360 (8)	0.0019 (6)	0.0055 (6)	−0.0031 (6)
C6	0.0217 (8)	0.0538 (11)	0.0358 (9)	−0.0009 (7)	0.0078 (6)	−0.0063 (8)
C7	0.0353 (9)	0.0620 (13)	0.0497 (12)	−0.0061 (9)	0.0087 (8)	−0.0183 (10)
C8	0.0459 (12)	0.0916 (18)	0.0571 (14)	−0.0110 (11)	0.0085 (10)	−0.0325 (13)
C9	0.0418 (11)	0.127 (2)	0.0368 (12)	0.0003 (13)	0.0000 (9)	−0.0178 (14)
C10	0.0416 (11)	0.0994 (18)	0.0379 (11)	0.0080 (11)	0.0044 (8)	0.0063 (11)
C11	0.0275 (9)	0.0650 (13)	0.0368 (10)	0.0045 (8)	0.0068 (7)	0.0022 (9)
C12	0.0494 (11)	0.0523 (12)	0.0462 (11)	0.0082 (9)	0.0084 (9)	0.0124 (9)
C13	0.0699 (15)	0.0734 (17)	0.0914 (19)	0.0241 (13)	0.0118 (14)	0.0160 (14)
C14	0.0615 (14)	0.0651 (15)	0.0912 (18)	−0.0046 (12)	0.0146 (13)	0.0000 (13)
C15	0.0779 (16)	0.0460 (12)	0.0748 (15)	−0.0053 (11)	0.0088 (12)	−0.0183 (11)
C16	0.105 (2)	0.0704 (18)	0.119 (2)	0.0113 (16)	0.0185 (19)	−0.0276 (17)
C17	0.112 (2)	0.0726 (19)	0.149 (3)	−0.0101 (17)	0.052 (2)	0.0129 (19)
N2	0.0293 (7)	0.0395 (8)	0.0274 (7)	0.0017 (6)	0.0088 (5)	0.0014 (6)
C18	0.0268 (8)	0.0430 (10)	0.0278 (8)	0.0027 (7)	0.0094 (6)	0.0025 (7)
C19	0.0283 (8)	0.0517 (11)	0.0331 (9)	0.0006 (7)	0.0075 (7)	0.0021 (8)
C20	0.0349 (9)	0.0684 (14)	0.0350 (10)	0.0016 (9)	0.0006 (7)	0.0059 (9)
C21	0.0421 (10)	0.0652 (14)	0.0452 (11)	0.0100 (9)	0.0049 (9)	0.0202 (10)
C22	0.0474 (11)	0.0426 (11)	0.0566 (12)	0.0070 (9)	0.0087 (9)	0.0094 (9)
C23	0.0369 (9)	0.0425 (10)	0.0411 (10)	0.0042 (8)	0.0079 (7)	0.0011 (8)
C24	0.0741 (14)	0.0396 (11)	0.0529 (12)	0.0029 (10)	−0.0070 (10)	−0.0074 (9)
C25	0.0680 (18)	0.169 (3)	0.123 (3)	−0.0252 (19)	0.0005 (17)	−0.086 (3)
C26	0.0954 (18)	0.0671 (15)	0.0580 (14)	0.0098 (13)	0.0073 (13)	−0.0158 (12)
C27	0.0462 (10)	0.0546 (12)	0.0350 (10)	−0.0058 (9)	−0.0028 (8)	−0.0057 (8)
C28	0.0825 (17)	0.0737 (16)	0.0654 (15)	−0.0171 (13)	0.0195 (13)	−0.0257 (12)
C29	0.0561 (12)	0.0678 (14)	0.0562 (13)	−0.0150 (11)	−0.0001 (10)	0.0076 (11)

Geometric parameters (Å, º) top

C1—C2	1.502 (2)	C16—H16A	0.980
C1—H1A	0.980	C16—H16B	0.980
C1—H1B	0.980	C16—H16C	0.980
C1—H1C	0.980	C17—H17A	0.980
C2—N1	1.326 (2)	C17—H17B	0.980
C2—C3	1.398 (2)	C17—H17C	0.980
C3—C4	1.401 (2)	N2—C18	1.428 (2)
C3—H3	0.950	N2—H2N	0.89 (3)
C4—N2	1.327 (2)	C18—C23	1.396 (2)
C4—C5	1.505 (2)	C18—C19	1.398 (2)
C5—H5A	0.980	C19—C20	1.390 (3)
C5—H5B	0.980	C19—C27	1.520 (3)
C5—H5C	0.980	C20—C21	1.370 (3)
N1—C6	1.424 (2)	C20—H20	0.950
N1—H1N	0.90 (3)	C21—C22	1.377 (3)
C6—C11	1.399 (3)	C21—H21	0.950
C6—C7	1.403 (3)	C22—C23	1.392 (3)
C7—C8	1.393 (3)	C22—H22	0.950
C7—C15	1.508 (3)	C23—C24	1.515 (3)
C8—C9	1.373 (4)	C24—C26	1.506 (3)
C8—H8	0.950	C24—C25	1.526 (4)
C9—C10	1.367 (3)	C24—H24	1.0000
C9—H9	0.950	C25—H25A	0.980
C10—C11	1.393 (3)	C25—H25B	0.980
C10—H10	0.950	C25—H25C	0.980
C11—C12	1.509 (3)	C26—H26A	0.980
C12—C13	1.524 (3)	C26—H26B	0.980
C12—C14	1.528 (3)	C26—H26C	0.980
C12—H12	1.000	C27—C29	1.522 (3)
C13—H13A	0.980	C27—C28	1.528 (3)
C13—H13B	0.980	C27—H27	1.000
C13—H13C	0.980	C28—H28A	0.980
C14—H14A	0.980	C28—H28B	0.980
C14—H14B	0.980	C28—H28C	0.980
C14—H14C	0.980	C29—H29A	0.980
C15—C16	1.520 (3)	C29—H29B	0.980
C15—C17	1.530 (4)	C29—H29C	0.980
C15—H15	1.000

C2—C1—H1A	109.5	H16A—C16—H16B	109.5
C2—C1—H1B	109.5	C15—C16—H16C	109.5
H1A—C1—H1B	109.5	H16A—C16—H16C	109.5
C2—C1—H1C	109.5	H16B—C16—H16C	109.5
H1A—C1—H1C	109.5	C15—C17—H17A	109.5
H1B—C1—H1C	109.5	C15—C17—H17B	109.5
N1—C2—C3	121.92 (15)	H17A—C17—H17B	109.5
N1—C2—C1	114.12 (14)	C15—C17—H17C	109.5
C3—C2—C1	123.89 (14)	H17A—C17—H17C	109.5
C2—C3—C4	129.70 (15)	H17B—C17—H17C	109.5
C2—C3—H3	115.1	C4—N2—C18	122.77 (13)
C4—C3—H3	115.1	C4—N2—H2N	126 (2)
N2—C4—C3	121.84 (14)	C18—N2—H2N	112 (2)
N2—C4—C5	114.06 (13)	C23—C18—C19	121.44 (15)
C3—C4—C5	124.05 (14)	C23—C18—N2	118.45 (15)
C4—C5—H5A	109.5	C19—C18—N2	119.89 (15)
C4—C5—H5B	109.5	C20—C19—C18	118.17 (17)
H5A—C5—H5B	109.5	C20—C19—C27	120.07 (16)
C4—C5—H5C	109.5	C18—C19—C27	121.75 (15)
H5A—C5—H5C	109.5	C21—C20—C19	121.24 (18)
H5B—C5—H5C	109.5	C21—C20—H20	119.4
C2—N1—C6	123.66 (13)	C19—C20—H20	119.4
C2—N1—H1N	126 (2)	C20—C21—C22	119.86 (18)
C6—N1—H1N	110 (2)	C20—C21—H21	120.1
C11—C6—C7	121.57 (17)	C22—C21—H21	120.1
C11—C6—N1	120.41 (16)	C21—C22—C23	121.35 (19)
C7—C6—N1	117.69 (16)	C21—C22—H22	119.3
C8—C7—C6	117.7 (2)	C23—C22—H22	119.3
C8—C7—C15	120.8 (2)	C22—C23—C18	117.88 (17)
C6—C7—C15	121.47 (18)	C22—C23—C24	120.62 (17)
C9—C8—C7	121.4 (2)	C18—C23—C24	121.50 (16)
C9—C8—H8	119.3	C26—C24—C23	113.27 (18)
C7—C8—H8	119.3	C26—C24—C25	110.6 (2)
C10—C9—C8	119.9 (2)	C23—C24—C25	111.22 (19)
C10—C9—H9	120.0	C26—C24—H24	107.1
C8—C9—H9	120.0	C23—C24—H24	107.1
C9—C10—C11	121.7 (2)	C25—C24—H24	107.1
C9—C10—H10	119.2	C24—C25—H25A	109.5
C11—C10—H10	119.2	C24—C25—H25B	109.5
C10—C11—C6	117.68 (19)	H25A—C25—H25B	109.5
C10—C11—C12	120.44 (19)	C24—C25—H25C	109.5
C6—C11—C12	121.85 (16)	H25A—C25—H25C	109.5
C11—C12—C13	112.25 (18)	H25B—C25—H25C	109.5
C11—C12—C14	111.35 (17)	C24—C26—H26A	109.5
C13—C12—C14	110.99 (18)	C24—C26—H26B	109.5
C11—C12—H12	107.3	H26A—C26—H26B	109.5
C13—C12—H12	107.3	C24—C26—H26C	109.5
C14—C12—H12	107.3	H26A—C26—H26C	109.5
C12—C13—H13A	109.5	H26B—C26—H26C	109.5
C12—C13—H13B	109.5	C19—C27—C29	110.92 (16)
H13A—C13—H13B	109.5	C19—C27—C28	111.62 (16)
C12—C13—H13C	109.5	C29—C27—C28	110.92 (17)
H13A—C13—H13C	109.5	C19—C27—H27	107.7
H13B—C13—H13C	109.5	C29—C27—H27	107.7
C12—C14—H14A	109.5	C28—C27—H27	107.7
C12—C14—H14B	109.5	C27—C28—H28A	109.5
H14A—C14—H14B	109.5	C27—C28—H28B	109.5
C12—C14—H14C	109.5	H28A—C28—H28B	109.5
H14A—C14—H14C	109.5	C27—C28—H28C	109.5
H14B—C14—H14C	109.5	H28A—C28—H28C	109.5
C7—C15—C16	112.4 (2)	H28B—C28—H28C	109.5
C7—C15—C17	111.3 (2)	C27—C29—H29A	109.5
C16—C15—C17	110.2 (2)	C27—C29—H29B	109.5
C7—C15—H15	107.6	H29A—C29—H29B	109.5
C16—C15—H15	107.6	C27—C29—H29C	109.5
C17—C15—H15	107.6	H29A—C29—H29C	109.5
C15—C16—H16A	109.5	H29B—C29—H29C	109.5
C15—C16—H16B	109.5

N1—C2—C3—C4	170.52 (16)	C8—C7—C15—C17	−74.4 (3)
C1—C2—C3—C4	−12.6 (3)	C6—C7—C15—C17	105.3 (2)
C2—C3—C4—N2	166.31 (16)	C3—C4—N2—C18	−10.9 (2)
C2—C3—C4—C5	−16.5 (3)	C5—C4—N2—C18	171.59 (15)
C3—C2—N1—C6	−13.0 (2)	C4—N2—C18—C23	−93.19 (19)
C1—C2—N1—C6	169.83 (15)	C4—N2—C18—C19	92.21 (19)
C2—N1—C6—C11	92.75 (19)	C23—C18—C19—C20	−2.1 (2)
C2—N1—C6—C7	−93.79 (19)	N2—C18—C19—C20	172.37 (14)
C11—C6—C7—C8	1.4 (2)	C23—C18—C19—C27	179.06 (15)
N1—C6—C7—C8	−171.93 (15)	N2—C18—C19—C27	−6.5 (2)
C11—C6—C7—C15	−178.29 (17)	C18—C19—C20—C21	0.0 (3)
N1—C6—C7—C15	8.3 (2)	C27—C19—C20—C21	178.93 (16)
C6—C7—C8—C9	0.5 (3)	C19—C20—C21—C22	1.5 (3)
C15—C7—C8—C9	−179.78 (19)	C20—C21—C22—C23	−0.9 (3)
C7—C8—C9—C10	−1.7 (3)	C21—C22—C23—C18	−1.0 (3)
C8—C9—C10—C11	1.0 (3)	C21—C22—C23—C24	178.80 (17)
C9—C10—C11—C6	0.8 (3)	C19—C18—C23—C22	2.5 (2)
C9—C10—C11—C12	179.03 (18)	N2—C18—C23—C22	−171.96 (15)
C7—C6—C11—C10	−2.1 (2)	C19—C18—C23—C24	−177.29 (16)
N1—C6—C11—C10	171.11 (15)	N2—C18—C23—C24	8.2 (2)
C7—C6—C11—C12	179.76 (16)	C22—C23—C24—C26	55.7 (3)
N1—C6—C11—C12	−7.0 (2)	C18—C23—C24—C26	−124.5 (2)
C10—C11—C12—C13	48.9 (2)	C22—C23—C24—C25	−69.6 (3)
C6—C11—C12—C13	−132.95 (18)	C18—C23—C24—C25	110.2 (2)
C10—C11—C12—C14	−76.2 (2)	C20—C19—C27—C29	−71.4 (2)
C6—C11—C12—C14	101.9 (2)	C18—C19—C27—C29	107.52 (18)
C8—C7—C15—C16	49.7 (3)	C20—C19—C27—C28	52.9 (2)
C6—C7—C15—C16	−130.6 (2)	C18—C19—C27—C28	−128.24 (19)

Experimental details

Crystal data
Chemical formula	C₂₉H₄₂N₂·0.5C₇H₈
M_r	464.71
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	26.655 (5), 18.004 (3), 12.623 (2)
β (°)	91.972 (3)
V (Å³)	6054.0 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.06
Crystal size (mm)	0.19 × 0.16 × 0.07

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.989, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	21824, 5322, 4677
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.141, 1.14
No. of reflections	5322
No. of parameters	296
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

C1—C2	1.502 (2)	C4—N2	1.327 (2)
C2—N1	1.326 (2)	C4—C5	1.505 (2)
C2—C3	1.398 (2)	N1—C6	1.424 (2)
C3—C4	1.401 (2)	N2—C18	1.428 (2)

N1—C2—C3	121.92 (15)	N2—C4—C5	114.06 (13)
N1—C2—C1	114.12 (14)	C3—C4—C5	124.05 (14)
C3—C2—C1	123.89 (14)	C2—N1—C6	123.66 (13)
C2—C3—C4	129.70 (15)	C4—N2—C18	122.77 (13)
N2—C4—C3	121.84 (14)

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2-(2,6-Diiso­propyl­phenyl­amino)-4-(2,6-diiso­propyl­phenyl­imino)-2-pentene toluene hemisolvate at 150 K