2,3-Bis{[2,3-dimethyl-6-(phenyl-vin-yl)phen-yl]imino}-butane.

In the title compound, C36H36N2, a product of the condensation reaction of 2,3-dimethyl-6-phenyl-vinyl-benzenamine and 2,3-butane-dione, the complete mol-ecule is generated by the application of an inversion centre. The central C-C bond in the 1,4-di-aza-butadiene fragment is trans-configured and situated about the inversion center. The dihedral angle between the ring attached to N and the 1,4-di-aza-butadiene plane is 78.24 (36)°, while the 1,4-di-aza-butadiene plane makes an angle of 30.71 (26)° with the phenyl ring.

Related literature

The title compound was synthesized as an α-di­imine ligand for transtion metals, see: Johnson et al. (1995 ▶); Gao et al. (2012 ▶); Zhang & Ye (2012 ▶); Sun et al. (2012 ▶); Popeney et al. (2012 ▶); Shi et al. (2012 ▶). For related structures, see: Helldörfer, Milius & Alt (2003 ▶); Helldörfer, Backhaus & Alt (2003 ▶); Popeney & Guan (2005 ▶); Kravchenko & Waymouth (1998 ▶).

Experimental

Crystal data

C36H36N2

M = 496.67

Monoclinic,

a = 9.613 (8) Å

b = 16.285 (14) Å

c = 9.639 (8) Å

β = 101.679 (9)°

V = 1478 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.06 mm−1

T = 296 K

0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.984, T max = 0.989

10305 measured reflections

2693 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.103

wR(F 2) = 0.327

S = 1.03

2693 reflections

175 parameters

84 restraints

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814000440/qm2103sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814000440/qm2103Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814000440/qm2103Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

C36H36N2	F(000) = 532
Mr = 496.67	Dx = 1.116 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.613 (8) Å	Cell parameters from 1803 reflections
b = 16.285 (14) Å	θ = 2.5–22.5°
c = 9.639 (8) Å	µ = 0.06 mm−1
β = 101.679 (9)°	T = 296 K
V = 1478 (2) Å3	Block, yellow
Z = 2	0.26 × 0.24 × 0.18 mm

Bruker APEXII CCD diffractometer	2693 independent reflections
Radiation source: fine-focus sealed tube	1374 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 25.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.984, Tmax = 0.989	k = −19→19
10305 measured reflections	l = −11→10

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)] = 0.103	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.327	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1098P)2 + 2.2955P] where P = (Fo2 + 2Fc2)/3
2693 reflections	(Δ/σ)max < 0.001
175 parameters	Δρmax = 0.46 e Å−3
84 restraints	Δρmin = −0.42 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
C1	0.7542 (5)	0.9715 (4)	0.3661 (7)	0.0873 (16)
C2	0.8434 (5)	1.0392 (4)	0.3706 (5)	0.0738 (15)
C3	0.9406 (5)	1.0398 (4)	0.2810 (6)	0.0795 (16)
C4	0.9452 (6)	0.9752 (5)	0.1928 (7)	0.0954 (19)
H4	1.0072	0.9770	0.1303	0.114*
C5	0.8604 (7)	0.9073 (5)	0.1938 (8)	0.107 (2)
H5	0.8682	0.8633	0.1344	0.128*
C6	0.7627 (6)	0.9037 (4)	0.2827 (9)	0.112 (2)
C7	0.6752 (7)	0.8283 (4)	0.2878 (10)	0.135 (2)
C8	0.7248 (9)	0.7605 (5)	0.3422 (13)	0.175 (3)
H8A	0.8211	0.7558	0.3819	0.210*
H8B	0.6649	0.7157	0.3421	0.210*
C9	0.5196 (6)	0.8376 (4)	0.2159 (9)	0.116 (2)
C10	0.4124 (7)	0.8072 (4)	0.2744 (8)	0.108 (2)
H10	0.4340	0.7810	0.3619	0.130*
C11	0.2722 (7)	0.8147 (5)	0.2058 (9)	0.110 (2)
H11	0.2004	0.7944	0.2481	0.132*
C12	0.2387 (7)	0.8512 (4)	0.0777 (8)	0.101 (2)
H12	0.1442	0.8555	0.0313	0.121*
C13	0.3433 (7)	0.8816 (5)	0.0169 (7)	0.109 (2)
H13	0.3207	0.9069	−0.0713	0.131*
C14	0.4836 (7)	0.8750 (4)	0.0858 (8)	0.107 (2)
H14	0.5547	0.8961	0.0436	0.128*
C15	0.8381 (7)	1.1086 (4)	0.4719 (7)	0.107 (2)
H15A	0.7756	1.1506	0.4254	0.160*
H15B	0.9317	1.1309	0.5026	0.160*
H15C	0.8038	1.0886	0.5524	0.160*
C16	1.0396 (6)	1.1122 (4)	0.2799 (7)	0.109 (2)
H16A	1.0944	1.1040	0.2081	0.163*
H16B	1.1023	1.1168	0.3707	0.163*
H16C	0.9848	1.1617	0.2601	0.163*
C17	0.5439 (5)	1.0046 (4)	0.4443 (6)	0.0981 (17)
C18	0.4816 (6)	1.0561 (5)	0.3171 (7)	0.114 (2)
H18A	0.5390	1.0508	0.2468	0.171*
H18B	0.4794	1.1126	0.3450	0.171*
H18C	0.3868	1.0378	0.2783	0.171*
N1	0.6610 (4)	0.9671 (3)	0.4649 (5)	0.0950 (14)

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.109 (4)	0.104 (4)	0.019 (3)	0.016 (2)	0.067 (3)
C2	0.052 (3)	0.095 (4)	0.072 (3)	0.016 (3)	0.008 (2)	0.035 (3)
C3	0.051 (3)	0.109 (4)	0.077 (4)	0.006 (3)	0.010 (3)	0.040 (3)
C4	0.070 (4)	0.131 (6)	0.089 (4)	0.020 (4)	0.023 (3)	0.024 (4)
C5	0.077 (4)	0.118 (6)	0.120 (5)	0.021 (4)	0.005 (4)	0.006 (4)
C6	0.058 (3)	0.089 (4)	0.177 (5)	0.011 (3)	−0.004 (3)	0.057 (4)
C7	0.081 (3)	0.098 (3)	0.207 (5)	0.002 (3)	−0.021 (3)	0.063 (3)
C8	0.105 (5)	0.098 (5)	0.294 (9)	0.008 (4)	−0.026 (6)	0.051 (6)
C9	0.070 (3)	0.085 (4)	0.180 (5)	−0.001 (3)	−0.007 (4)	0.047 (4)
C10	0.103 (5)	0.104 (5)	0.107 (5)	−0.026 (4)	−0.005 (4)	0.017 (4)
C11	0.092 (5)	0.123 (6)	0.115 (6)	−0.036 (4)	0.022 (4)	−0.024 (5)
C12	0.081 (4)	0.129 (6)	0.089 (5)	0.007 (4)	0.007 (4)	−0.030 (4)
C13	0.088 (4)	0.150 (6)	0.085 (4)	0.021 (4)	0.011 (4)	0.004 (4)
C14	0.080 (4)	0.119 (5)	0.122 (5)	0.017 (4)	0.021 (4)	0.030 (4)
C15	0.100 (5)	0.119 (5)	0.103 (5)	0.017 (4)	0.023 (4)	0.025 (4)
C16	0.067 (3)	0.142 (6)	0.115 (5)	−0.011 (4)	0.010 (3)	0.050 (4)
C17	0.058 (2)	0.133 (4)	0.107 (3)	0.022 (3)	0.026 (2)	0.076 (3)
C18	0.081 (4)	0.159 (5)	0.108 (4)	0.036 (4)	0.030 (3)	0.082 (4)
N1	0.054 (2)	0.127 (3)	0.107 (3)	0.020 (2)	0.024 (2)	0.073 (2)

C1—C6	1.379 (10)	C11—C12	1.350 (9)
C1—C2	1.392 (8)	C11—H11	0.9300
C1—N1	1.435 (7)	C12—C13	1.356 (9)
C2—C3	1.395 (7)	C12—H12	0.9300
C2—C15	1.500 (8)	C13—C14	1.381 (9)
C3—C4	1.359 (9)	C13—H13	0.9300
C3—C16	1.516 (8)	C14—H14	0.9300
C4—C5	1.375 (9)	C15—H15A	0.9600
C4—H4	0.9300	C15—H15B	0.9600
C5—C6	1.395 (9)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.495 (9)	C16—H16B	0.9600
C7—C8	1.273 (9)	C16—H16C	0.9600
C7—C9	1.523 (9)	C17—N1	1.261 (6)
C8—H8A	0.9300	C17—C17i	1.502 (10)
C8—H8B	0.9300	C17—C18	1.506 (7)
C9—C10	1.364 (9)	C18—H18A	0.9600
C9—C14	1.373 (9)	C18—H18B	0.9600
C10—C11	1.381 (9)	C18—H18C	0.9600
C10—H10	0.9300
C6—C1—C2	123.0 (5)	C10—C11—H11	119.8
C6—C1—N1	117.7 (6)	C11—C12—C13	119.7 (6)
C2—C1—N1	118.8 (7)	C11—C12—H12	120.1
C1—C2—C3	118.2 (6)	C13—C12—H12	120.1
C1—C2—C15	121.0 (5)	C12—C13—C14	120.0 (7)
C3—C2—C15	120.8 (6)	C12—C13—H13	120.0
C4—C3—C2	119.5 (6)	C14—C13—H13	120.0
C4—C3—C16	119.8 (6)	C9—C14—C13	121.0 (6)
C2—C3—C16	120.7 (6)	C9—C14—H14	119.5
C3—C4—C5	121.6 (6)	C13—C14—H14	119.5
C3—C4—H4	119.2	C2—C15—H15A	109.5
C5—C4—H4	119.2	C2—C15—H15B	109.5
C4—C5—C6	120.8 (7)	H15A—C15—H15B	109.5
C4—C5—H5	119.6	C2—C15—H15C	109.5
C6—C5—H5	119.6	H15A—C15—H15C	109.5
C1—C6—C5	116.8 (6)	H15B—C15—H15C	109.5
C1—C6—C7	122.6 (8)	C3—C16—H16A	109.5
C5—C6—C7	120.5 (9)	C3—C16—H16B	109.5
C8—C7—C6	124.0 (6)	H16A—C16—H16B	109.5
C8—C7—C9	121.7 (7)	C3—C16—H16C	109.5
C6—C7—C9	114.3 (5)	H16A—C16—H16C	109.5
C7—C8—H8A	120.0	H16B—C16—H16C	109.5
C7—C8—H8B	120.0	N1—C17—C17i	116.8 (5)
H8A—C8—H8B	120.0	N1—C17—C18	126.4 (5)
C10—C9—C14	117.8 (6)	C17i—C17—C18	116.7 (5)
C10—C9—C7	122.0 (7)	C17—C18—H18A	109.5
C14—C9—C7	120.1 (7)	C17—C18—H18B	109.5
C9—C10—C11	121.0 (7)	H18A—C18—H18B	109.5
C9—C10—H10	119.5	C17—C18—H18C	109.5
C11—C10—H10	119.5	H18A—C18—H18C	109.5
C12—C11—C10	120.4 (7)	H18B—C18—H18C	109.5
C12—C11—H11	119.8	C17—N1—C1	121.8 (4)
C6—C1—C2—C3	3.4 (7)	C1—C6—C7—C9	74.5 (10)
N1—C1—C2—C3	175.4 (4)	C5—C6—C7—C9	−106.9 (8)
C6—C1—C2—C15	−174.9 (5)	C8—C7—C9—C10	44.8 (14)
N1—C1—C2—C15	−2.9 (7)	C6—C7—C9—C10	−137.7 (8)
C1—C2—C3—C4	0.1 (7)	C8—C7—C9—C14	−132.8 (10)
C15—C2—C3—C4	178.4 (5)	C6—C7—C9—C14	44.7 (12)
C1—C2—C3—C16	179.4 (5)	C14—C9—C10—C11	−0.8 (11)
C15—C2—C3—C16	−2.4 (7)	C7—C9—C10—C11	−178.5 (7)
C2—C3—C4—C5	−2.9 (8)	C9—C10—C11—C12	1.1 (11)
C16—C3—C4—C5	177.9 (5)	C10—C11—C12—C13	−0.8 (11)
C3—C4—C5—C6	2.2 (9)	C11—C12—C13—C14	0.1 (11)
C2—C1—C6—C5	−4.1 (8)	C10—C9—C14—C13	0.1 (11)
N1—C1—C6—C5	−176.1 (5)	C7—C9—C14—C13	177.9 (7)
C2—C1—C6—C7	174.6 (5)	C12—C13—C14—C9	0.2 (11)
N1—C1—C6—C7	2.5 (8)	C17i—C17—N1—C1	−179.8 (7)
C4—C5—C6—C1	1.3 (9)	C18—C17—N1—C1	1.9 (12)
C4—C5—C6—C7	−177.4 (6)	C6—C1—N1—C17	−106.0 (7)
C1—C6—C7—C8	−108.0 (11)	C2—C1—N1—C17	81.6 (8)
C5—C6—C7—C8	70.6 (13)