2,3-Bis(2-tert-butyl­phenyl­imino)butane

In the title compound, C₂₄H₃₂N₂, there is one half-mol­ecule in the asymmetric unit, the other half being generated by inversion. All bond lengths and angles show normal values. The deviation from a planar arrangement can be attributed to non-classical hydrogen bonds and steric factors.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.104
• Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT391_ALERT_3_C Deviating Methyl C8      H-C-H Bond Angle ......     100.40 Deg.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: COSMO/APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

2,3-Bis(2-tert-butylphenylimino)butane

Crystal data

C24H32N2	F(000) = 380
Mr = 348.52	Dx = 1.086 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 87 reflections
a = 8.3786 (3) Å	θ = 2.1–57.9°
b = 20.3282 (8) Å	µ = 0.06 mm^−1
c = 6.6802 (3) Å	T = 295 K
β = 110.485 (2)°	Block, yellow
V = 1065.83 (7) Å^3	0.2 × 0.11 × 0.07 mm
Z = 2

Data collection

Bruker APEX-II CCD area-detector diffractometer	Rint = 0.044
Graphite monochromator	θmax = 25.5°, θmin = 3.4°
φ and ω scans	h = −10→10
10277 measured reflections	k = −24→24
1972 independent reflections	l = −8→7
1189 reflections with I > 2σ(I)

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.059P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 0.104	Δρmax = 0.13 e Å^−3
S = 0.96	Δρmin = −0.11 e Å^−3
1972 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
183 parameters	Extinction coefficient: 0.052 (6)
0 restraints

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
H3	0.836 (2)	0.6883 (8)	0.629 (3)	0.073 (5)*
H4	0.610 (2)	0.7558 (9)	0.658 (3)	0.073 (5)*
H5	0.326 (2)	0.7265 (8)	0.484 (3)	0.070 (5)*
H8A	0.532 (2)	0.5831 (10)	−0.218 (4)	0.100 (7)*
H8B	0.703 (4)	0.5735 (12)	−0.043 (4)	0.143 (10)*
H8C	0.584 (3)	0.6279 (12)	−0.004 (4)	0.115 (8)*
H10A	0.226 (2)	0.5214 (10)	0.319 (3)	0.096 (7)*
H10B	0.174 (3)	0.5660 (12)	0.494 (5)	0.128 (9)*
H10C	0.032 (3)	0.5456 (10)	0.268 (3)	0.098 (7)*
H11A	0.091 (3)	0.7188 (15)	0.214 (4)	0.136 (10)*
H11B	0.092 (3)	0.6821 (12)	0.428 (4)	0.121 (10)*
H11C	−0.056 (3)	0.6602 (10)	0.188 (4)	0.111 (7)*
H12C	0.176 (3)	0.6531 (12)	−0.081 (4)	0.116 (8)*
H12B	0.018 (3)	0.6048 (10)	−0.077 (4)	0.118 (8)*
H12A	0.205 (3)	0.5760 (11)	−0.037 (4)	0.114 (8)*
H2	0.7613 (19)	0.5912 (7)	0.418 (2)	0.057 (4)*
C1	0.50739 (17)	0.60308 (7)	0.3254 (2)	0.0407 (4)
C2	0.67533 (19)	0.62098 (8)	0.4342 (2)	0.0487 (4)
C3	0.7142 (2)	0.67720 (8)	0.5572 (3)	0.0575 (5)
C4	0.5859 (3)	0.71613 (9)	0.5717 (3)	0.0620 (5)
C5	0.4186 (2)	0.69813 (8)	0.4652 (3)	0.0570 (5)
C6	0.37251 (17)	0.64166 (7)	0.3415 (2)	0.0457 (4)
C7	0.51557 (17)	0.53366 (6)	0.0480 (2)	0.0399 (4)
C8	0.5822 (3)	0.58474 (10)	−0.0636 (3)	0.0627 (5)
C9	0.18498 (19)	0.62199 (8)	0.2338 (3)	0.0595 (5)
C10	0.1519 (3)	0.55745 (11)	0.3324 (5)	0.0821 (7)
C11	0.0640 (3)	0.67436 (14)	0.2670 (6)	0.0998 (9)
C12	0.1386 (3)	0.61423 (13)	−0.0075 (4)	0.0800 (7)
N1	0.47600 (14)	0.54226 (5)	0.21424 (19)	0.0432 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0557 (8)	0.0339 (8)	0.0358 (8)	−0.0025 (6)	0.0203 (7)	−0.0006 (6)
C2	0.0547 (9)	0.0458 (10)	0.0454 (10)	−0.0026 (7)	0.0171 (7)	0.0012 (8)
C3	0.0692 (11)	0.0543 (11)	0.0421 (10)	−0.0158 (9)	0.0111 (8)	0.0029 (8)
C4	0.1017 (15)	0.0414 (11)	0.0470 (10)	−0.0137 (10)	0.0312 (10)	−0.0074 (9)
C5	0.0826 (12)	0.0409 (10)	0.0588 (11)	−0.0001 (9)	0.0387 (9)	−0.0043 (8)
C6	0.0598 (9)	0.0373 (9)	0.0456 (9)	0.0002 (7)	0.0256 (7)	0.0009 (7)
C7	0.0473 (8)	0.0354 (8)	0.0386 (8)	0.0014 (6)	0.0171 (7)	0.0008 (6)
C8	0.1008 (15)	0.0441 (12)	0.0548 (13)	−0.0181 (10)	0.0416 (11)	−0.0050 (9)
C9	0.0553 (9)	0.0512 (11)	0.0767 (13)	0.0020 (7)	0.0289 (8)	−0.0029 (9)
C10	0.0725 (13)	0.0698 (15)	0.113 (2)	−0.0117 (11)	0.0437 (13)	0.0056 (13)
C11	0.0668 (14)	0.0812 (19)	0.161 (3)	0.0083 (11)	0.0524 (17)	−0.0189 (18)
C12	0.0590 (12)	0.0918 (17)	0.0749 (16)	0.0030 (11)	0.0054 (10)	0.0025 (12)
N1	0.0527 (7)	0.0370 (7)	0.0429 (8)	0.0012 (5)	0.0208 (6)	−0.0019 (6)

Geometric parameters (Å, º)

C1—C2	1.387 (2)	C8—H8A	0.97 (2)
C1—C6	1.4103 (19)	C8—H8B	1.00 (3)
C1—N1	1.4185 (17)	C8—H8C	0.96 (3)
C2—C3	1.378 (2)	C9—C12	1.528 (3)
C2—H2	0.976 (15)	C9—C10	1.536 (3)
C3—C4	1.365 (2)	C9—C11	1.539 (3)
C3—H3	0.989 (17)	C10—H10A	0.98 (2)
C4—C5	1.381 (2)	C10—H10B	1.04 (3)
C4—H4	0.971 (18)	C10—H10C	0.97 (2)
C5—C6	1.388 (2)	C11—H11A	1.02 (3)
C5—H5	1.006 (16)	C11—H11B	1.03 (3)
C6—C9	1.535 (2)	C11—H11C	1.00 (2)
C7—N1	1.2772 (17)	C12—H12C	1.03 (3)
C7—C8	1.496 (2)	C12—H12B	0.97 (3)
C7—C7^i	1.495 (3)	C12—H12A	1.02 (2)
C2—C1—C6	120.46 (13)	H8B—C8—H8C	106.4 (18)
C2—C1—N1	118.11 (12)	C12—C9—C6	111.24 (14)
C6—C1—N1	121.19 (12)	C12—C9—C10	110.28 (19)
C3—C2—C1	120.97 (16)	C6—C9—C10	109.27 (15)
C3—C2—H2	123.5 (9)	C12—C9—C11	106.6 (2)
C1—C2—H2	115.6 (9)	C6—C9—C11	111.71 (16)
C4—C3—C2	119.69 (17)	C10—C9—C11	107.60 (18)
C4—C3—H3	122.6 (9)	C9—C10—H10A	112.7 (12)
C2—C3—H3	117.7 (9)	C9—C10—H10B	107.9 (14)
C3—C4—C5	119.49 (17)	H10A—C10—H10B	109.0 (18)
C3—C4—H4	121.2 (9)	C9—C10—H10C	109.5 (12)
C5—C4—H4	119.3 (9)	H10A—C10—H10C	111.1 (16)
C4—C5—C6	123.14 (16)	H10B—C10—H10C	106.5 (18)
C4—C5—H5	118.1 (9)	C9—C11—H11A	109.1 (15)
C6—C5—H5	118.8 (9)	C9—C11—H11B	109.6 (14)
C5—C6—C1	116.24 (14)	H11A—C11—H11B	103 (2)
C5—C6—C9	121.36 (14)	C9—C11—H11C	108.3 (13)
C1—C6—C9	122.38 (13)	H11A—C11—H11C	111.7 (19)
N1—C7—C8	126.45 (14)	H11B—C11—H11C	114.6 (18)
N1—C7—C7^i	116.03 (15)	C9—C12—H12C	114.5 (13)
C8—C7—C7^i	117.46 (16)	C9—C12—H12B	111.2 (13)
C7—C8—H8A	114.1 (12)	H12C—C12—H12B	111.0 (17)
C7—C8—H8B	107.9 (15)	C9—C12—H12A	109.4 (13)
H8A—C8—H8B	100.5 (19)	H12C—C12—H12A	102.2 (17)
C7—C8—H8C	112.5 (13)	H12B—C12—H12A	107.9 (18)
H8A—C8—H8C	114.2 (18)	C7—N1—C1	121.16 (11)
C6—C1—C2—C3	−1.1 (2)	C5—C6—C9—C12	123.53 (17)
N1—C1—C2—C3	−175.55 (13)	C1—C6—C9—C12	−58.0 (2)
C1—C2—C3—C4	−0.3 (2)	C5—C6—C9—C10	−114.47 (19)
C2—C3—C4—C5	0.9 (2)	C1—C6—C9—C10	64.0 (2)
C3—C4—C5—C6	−0.1 (2)	C5—C6—C9—C11	4.5 (3)
C4—C5—C6—C1	−1.2 (2)	C1—C6—C9—C11	−177.05 (19)
C4—C5—C6—C9	177.32 (15)	C8—C7—N1—C1	−5.9 (2)
C2—C1—C6—C5	1.8 (2)	C7^i—C7—N1—C1	176.91 (14)
N1—C1—C6—C5	176.09 (13)	C2—C1—N1—C7	−68.51 (17)
C2—C1—C6—C9	−176.73 (14)	C6—C1—N1—C7	117.09 (15)
N1—C1—C6—C9	−2.5 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N1	0.98 (2)	2.47 (2)	3.097 (3)	121.5 (15)
C12—H12A···N1	1.02 (2)	2.41 (3)	3.065 (3)	121.7 (18)