2-[2-(2,6-Di­methyl­phenyl­amino)­phenyl­methyl­ene­amino]-1,3-diiso­propyl­benzene

The ortho-disubstituted aromatic ring in the title compound, C₂₇H₃₂N₂, is twisted by 76.1 (1)° with respect to the iso­propyl-substituted ring and by 89.3 (1)° with respect to the methyl-substituted ring. The amino N atom is linked intramolecularly to the imino N by a hydrogen bond [N...N = 2.686 (2) Å].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.052
• wR factor = 0.179
• Data-to-parameter ratio = 19.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT242_ALERT_2_A Check Low    U(eq) as Compared to Neighbors ....        C10

Author Response: The C10 atom belongs to an isopropyl group.

Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.98 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.76 Ratio
PLAT242_ALERT_2_B Check Low    U(eq) as Compared to Neighbors ....         C7

Author Response: The C10 atom belongs to an isopropyl group.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C21

Author Response: The C10 atom belongs to an isopropyl group.

   1 ALERT level A = In general: serious problem
   3 ALERT level B = Potentially serious problem
   2 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
   4 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

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

2-[2-(2,6-Dimethylphenylamino)phenylmethyleneamino]-1,3-diisopropylbenzene

Crystal data

C27H32N2	F(000) = 832
Mr = 384.55	Dx = 1.079 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 854 reflections
a = 12.013 (2) Å	θ = 2.7–23.1°
b = 7.789 (1) Å	µ = 0.06 mm^−1
c = 25.542 (3) Å	T = 293 K
β = 97.802 (3)°	Block, yellow
V = 2367.9 (5) Å^3	0.49 × 0.48 × 0.43 mm
Z = 4

Data collection

Bruker SMART 1K area-detector diffractometer	2681 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 27.1°, θmin = 1.6°
φ and ω scans	h = −15→13
13131 measured reflections	k = −4→9
5184 independent reflections	l = −32→32

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0863P)^2 + 0.2352P] where P = (Fo^2 + 2Fc^2)/3
5184 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

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

	x	y	z	Uiso*/Ueq
N1	0.4781 (1)	0.6477 (2)	0.6552 (1)	0.052 (1)
N2	0.3146 (1)	0.5855 (2)	0.5748 (1)	0.066 (1)
C1	0.5491 (1)	0.7591 (2)	0.6886 (1)	0.054 (1)
C2	0.6407 (2)	0.8332 (3)	0.6685 (1)	0.066 (1)
C3	0.7042 (2)	0.9517 (3)	0.6998 (1)	0.091 (1)
C4	0.6784 (2)	0.9962 (4)	0.7486 (1)	0.108 (1)
C5	0.5885 (2)	0.9226 (4)	0.7673 (1)	0.102 (1)
C6	0.5215 (2)	0.8032 (3)	0.7381 (1)	0.071 (1)
C7	0.6672 (2)	0.7854 (3)	0.6144 (1)	0.084 (1)
C8	0.6124 (3)	0.9041 (5)	0.5722 (1)	0.144 (1)
C9	0.7913 (2)	0.7689 (5)	0.6109 (1)	0.141 (1)
C10	0.4185 (2)	0.7298 (4)	0.7589 (1)	0.089 (1)
C11	0.3348 (3)	0.8677 (6)	0.7684 (2)	0.170 (2)
C12	0.4487 (3)	0.6200 (7)	0.8064 (2)	0.196 (2)
C13	0.4804 (1)	0.4868 (2)	0.6621 (1)	0.052 (1)
C14	0.4076 (1)	0.3659 (2)	0.6313 (1)	0.049 (1)
C15	0.4159 (2)	0.1926 (2)	0.6446 (1)	0.067 (1)
C16	0.3477 (2)	0.0718 (3)	0.6179 (1)	0.080 (1)
C17	0.2691 (2)	0.1221 (3)	0.5766 (1)	0.077 (1)
C18	0.2580 (2)	0.2903 (2)	0.5622 (1)	0.066 (1)
C19	0.3259 (1)	0.4164 (2)	0.5890 (1)	0.051 (1)
C20	0.2298 (2)	0.6483 (2)	0.5350 (1)	0.058 (1)
C21	0.1259 (2)	0.6937 (3)	0.5492 (1)	0.071 (1)
C22	0.0454 (2)	0.7570 (3)	0.5105 (1)	0.088 (1)
C23	0.0658 (2)	0.7726 (3)	0.4600 (1)	0.095 (1)
C24	0.1680 (2)	0.7291 (3)	0.4462 (1)	0.093 (1)
C25	0.2536 (2)	0.6664 (3)	0.4836 (1)	0.072 (1)
C26	0.1023 (3)	0.6751 (4)	0.6050 (1)	0.118 (1)
C27	0.3675 (2)	0.6233 (4)	0.4697 (1)	0.110 (1)
H2	0.360 (2)	0.660 (3)	0.5933 (9)	0.085 (7)*
H3	0.7658	1.0024	0.6875	0.109*
H4	0.7222	1.0765	0.7690	0.130*
H5	0.5720	0.9536	0.8005	0.122*
H7	0.6344	0.6716	0.6065	0.100*
H8A	0.6327	0.8705	0.5386	0.216*
H8B	0.6371	1.0196	0.5801	0.216*
H8C	0.5323	0.8981	0.5710	0.216*
H9A	0.8244	0.6882	0.6368	0.211*
H9B	0.8268	0.8787	0.6172	0.211*
H9C	0.8015	0.7293	0.5762	0.211*
H10	0.3809	0.6551	0.7311	0.107*
H11a	0.3077	0.9231	0.7355	0.254*
H11b	0.3708	0.9509	0.7928	0.254*
H11c	0.2730	0.8167	0.7828	0.254*
H12a	0.5005	0.5327	0.7986	0.295*
H12b	0.3822	0.5671	0.8159	0.295*
H12c	0.4831	0.6893	0.8352	0.295*
H13	0.5328	0.4434	0.6890	0.062*
H15	0.4693	0.1580	0.6724	0.081*
H16	0.3545	−0.0432	0.6276	0.096*
H17	0.2228	0.0403	0.5582	0.093*
H18	0.2043	0.3216	0.5341	0.079*
H22	−0.0242	0.7896	0.5193	0.105*
H23	0.0096	0.8134	0.4343	0.114*
H24	0.1807	0.7415	0.4112	0.112*
H26a	0.1610	0.7296	0.6284	0.177*
H26b	0.0991	0.5555	0.6137	0.177*
H26c	0.0317	0.7284	0.6086	0.177*
H27a	0.3675	0.6374	0.4323	0.164*
H27b	0.3856	0.5065	0.4793	0.164*
H27c	0.4224	0.6985	0.4884	0.164*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.047 (1)	0.048 (1)	0.058 (1)	−0.003 (1)	−0.004 (1)	0.001 (1)
N2	0.065 (1)	0.043 (1)	0.079 (1)	−0.005 (1)	−0.025 (1)	0.005 (1)
C1	0.043 (1)	0.052 (1)	0.062 (1)	−0.001 (1)	−0.009 (1)	−0.003 (1)
C2	0.049 (1)	0.059 (1)	0.088 (2)	−0.006 (1)	−0.001 (1)	0.001 (1)
C3	0.059 (1)	0.081 (2)	0.129 (2)	−0.019 (1)	−0.004 (1)	−0.006 (2)
C4	0.086 (2)	0.106 (2)	0.124 (2)	−0.026 (2)	−0.020 (2)	−0.043 (2)
C5	0.089 (2)	0.119 (2)	0.091 (2)	−0.016 (2)	−0.006 (1)	−0.041 (2)
C6	0.060 (1)	0.083 (1)	0.066 (1)	−0.007 (1)	−0.005 (1)	−0.014 (1)
C7	0.069 (2)	0.088 (2)	0.098 (2)	−0.011 (1)	0.025 (1)	0.005 (1)
C8	0.126 (3)	0.201 (4)	0.107 (2)	0.032 (3)	0.022 (2)	0.030 (2)
C9	0.090 (2)	0.189 (4)	0.149 (3)	0.032 (2)	0.038 (2)	0.017 (3)
C10	0.082 (2)	0.119 (2)	0.068 (1)	−0.011 (2)	0.015 (1)	−0.018 (1)
C11	0.118 (3)	0.184 (4)	0.220 (4)	0.013 (3)	0.074 (3)	−0.028 (3)
C12	0.139 (3)	0.300 (6)	0.147 (3)	−0.034 (4)	0.011 (3)	0.114 (4)
C13	0.044 (1)	0.054 (1)	0.057 (1)	0.005 (1)	0.000 (1)	0.003 (1)
C14	0.043 (1)	0.045 (1)	0.059 (1)	0.003 (1)	0.004 (1)	0.002 (1)
C15	0.062 (1)	0.051 (1)	0.086 (1)	0.006 (1)	−0.002 (1)	0.007 (1)
C16	0.083 (2)	0.041 (1)	0.113 (2)	0.000 (1)	0.000 (1)	0.003 (1)
C17	0.073 (1)	0.047 (1)	0.107 (2)	−0.010 (1)	−0.005 (1)	−0.007 (1)
C18	0.058 (1)	0.052 (1)	0.083 (1)	−0.007 (1)	−0.010 (1)	−0.003 (1)
C19	0.047 (1)	0.043 (1)	0.063 (1)	−0.002 (1)	0.003 (1)	−0.001 (1)
C20	0.054 (1)	0.041 (1)	0.073 (1)	−0.003 (1)	−0.015 (1)	0.003 (1)
C21	0.058 (1)	0.067 (1)	0.084 (2)	−0.007 (1)	−0.004 (1)	0.004 (1)
C22	0.053 (1)	0.094 (2)	0.111 (2)	0.004 (1)	−0.008 (1)	0.014 (2)
C23	0.072 (2)	0.099 (2)	0.104 (2)	0.009 (1)	−0.027 (2)	0.020 (2)
C24	0.101 (2)	0.096 (2)	0.076 (2)	0.009 (2)	−0.009 (1)	0.015 (1)
C25	0.075 (1)	0.063 (1)	0.074 (1)	0.008 (1)	−0.005 (1)	0.003 (1)
C26	0.097 (2)	0.155 (3)	0.106 (2)	0.001 (2)	0.024 (2)	0.014 (2)
C27	0.100 (2)	0.119 (2)	0.111 (2)	0.032 (2)	0.023 (2)	0.004 (2)

Geometric parameters (Å, º)

N1—C1	1.418 (2)	C3—H3	0.93
N1—C13	1.265 (2)	C4—H4	0.93
N2—C19	1.368 (2)	C5—H5	0.93
N2—C20	1.424 (2)	C7—H7	0.98
C1—C6	1.393 (3)	C8—H8a	0.96
C1—C2	1.400 (3)	C8—H8b	0.96
C2—C3	1.381 (3)	C8—H8c	0.96
C2—C7	1.507 (3)	C9—H9a	0.96
C3—C4	1.369 (4)	C9—H9b	0.96
C4—C5	1.365 (4)	C9—H9c	0.96
C5—C6	1.381 (3)	C10—H10	0.98
C6—C10	1.523 (3)	C11—H11a	0.96
C7—C8	1.502 (4)	C11—H11b	0.96
C7—C9	1.511 (4)	C11—H11c	0.96
C10—C12	1.487 (4)	C12—H12a	0.96
C10—C11	1.513 (4)	C12—H12b	0.96
C13—C14	1.444 (2)	C12—H12c	0.96
C14—C15	1.392 (2)	C13—H13	0.93
C14—C19	1.413 (2)	C15—H15	0.93
C15—C16	1.367 (3)	C16—H16	0.93
C16—C17	1.374 (3)	C17—H17	0.93
C17—C18	1.362 (3)	C18—H18	0.93
C18—C19	1.396 (2)	C22—H22	0.93
C20—C25	1.390 (3)	C23—H23	0.93
C20—C21	1.391 (3)	C24—H24	0.93
C21—C22	1.378 (3)	C26—H26a	0.96
C21—C26	1.496 (3)	C26—H26b	0.96
C22—C23	1.352 (4)	C26—H26c	0.96
C23—C24	1.366 (4)	C27—H27a	0.96
C24—C25	1.394 (3)	C27—H27b	0.96
C25—C27	1.498 (3)	C27—H27c	0.96
N2—H2	0.89 (2)
C1—N1—C13	121.4 (2)	C7—C8—H8b	109.5
C19—N2—C20	123.8 (2)	H8a—C8—H8b	109.5
C2—C1—C6	121.8 (2)	C7—C8—H8c	109.5
C6—C1—N1	120.0 (2)	H8a—C8—H8c	109.5
C2—C1—N1	118.0 (2)	H8b—C8—H8c	109.5
C1—C2—C3	117.6 (2)	C7—C9—H9a	109.5
C1—C2—C7	120.6 (2)	C7—C9—H9b	109.5
C3—C2—C7	121.8 (2)	H9a—C9—H9b	109.5
C2—C3—C4	121.4 (2)	C7—C9—H9c	109.5
C3—C4—C5	119.9 (2)	H9a—C9—H9c	109.5
C4—C5—C6	121.7 (2)	H9b—C9—H9c	109.5
C1—C6—C5	117.6 (2)	C12—C10—H10	106.6
C1—C6—C10	122.0 (2)	C11—C10—H10	106.6
C5—C6—C10	120.4 (2)	C6—C10—H10	106.6
C2—C7—C8	112.3 (2)	C10—C11—H11a	109.5
C2—C7—C9	114.2 (2)	C10—C11—H11b	109.5
C8—C7—C9	110.5 (2)	H11a—C11—H11b	109.5
C6—C10—C11	112.2 (2)	C10—C11—H11c	109.5
C6—C10—C12	112.4 (2)	H11a—C11—H11c	109.5
C11—C10—C12	111.9 (3)	H11b—C11—H11c	109.5
N1—C13—C14	124.7 (2)	C10—C12—H12a	109.5
C13—C14—C15	118.9 (2)	C10—C12—H12b	109.5
C13—C14—C19	122.8 (2)	H12a—C12—H12b	109.5
C15—C14—C19	118.4 (2)	C10—C12—H12c	109.5
C14—C15—C16	121.9 (2)	H12a—C12—H12c	109.5
C15—C16—C17	119.3 (2)	H12b—C12—H12c	109.5
C16—C17—C18	120.9 (2)	N1—C13—H13	117.6
C17—C18—C19	121.0 (2)	C14—C13—H13	117.6
N2—C19—C14	120.3 (2)	C16—C15—H15	119.1
N2—C19—C18	121.1 (2)	C14—C15—H15	119.1
C18—C19—C14	118.6 (2)	C15—C16—H16	120.4
C21—C20—C25	121.9 (2)	C17—C16—H16	120.4
C25—C20—N2	119.3 (2)	C18—C17—H17	119.6
C21—C20—N2	118.8 (2)	C16—C17—H17	119.6
C20—C21—C22	118.1 (2)	C17—C18—H18	119.5
C20—C21—C26	121.1 (2)	C19—C18—H18	119.5
C22—C21—C26	120.8 (2)	C23—C22—H22	119.5
C21—C22—C23	121.1 (2)	C21—C22—H22	119.5
C22—C23—C24	120.7 (2)	C22—C23—H23	119.6
C23—C24—C25	121.0 (2)	C24—C23—H23	119.6
C20—C25—C24	117.2 (2)	C23—C24—H24	119.5
C20—C25—C27	120.9 (2)	C25—C24—H24	119.5
C24—C25—C27	121.9 (2)	C21—C26—H26a	109.5
C19—N2—H2	117 (1)	C21—C26—H26b	109.5
C20—N2—H2	119 (1)	H26a—C26—H26b	109.5
C4—C3—H3	119.3	C21—C26—H26c	109.5
C2—C3—H3	119.3	H26a—C26—H26c	109.5
C5—C4—H4	120.0	H26b—C26—H26c	109.5
C3—C4—H4	120.0	C25—C27—H27a	109.5
C4—C5—H5	119.1	C25—C27—H27b	109.5
C6—C5—H5	119.1	H27a—C27—H27b	109.5
C8—C7—H7	106.5	C25—C27—H27c	109.5
C2—C7—H7	106.5	H27a—C27—H27c	109.5
C9—C7—H7	106.5	H27b—C27—H27c	109.5
C7—C8—H8a	109.5
C13—N1—C1—C6	−79.0 (2)	C13—C14—C15—C16	178.5 (2)
C13—N1—C1—C2	106.3 (2)	C14—C15—C16—C17	0.4 (3)
C6—C1—C2—C3	0.5 (3)	C15—C16—C17—C18	−0.4 (4)
N1—C1—C2—C3	175.1 (2)	C16—C17—C18—C19	−0.1 (3)
C6—C1—C2—C7	−178.8 (2)	C20—N2—C19—C18	4.5 (3)
N1—C1—C2—C7	−4.3 (3)	C20—N2—C19—C14	−175.7 (2)
C1—C2—C3—C4	−0.3 (3)	C17—C18—C19—N2	−179.7 (2)
C7—C2—C3—C4	179.0 (2)	C17—C18—C19—C14	0.5 (3)
C2—C3—C4—C5	0.2 (4)	C15—C14—C19—N2	179.8 (2)
C3—C4—C5—C6	−0.2 (5)	C13—C14—C19—N2	1.4 (3)
C4—C5—C6—C1	0.3 (4)	C15—C14—C19—C18	−0.4 (3)
C4—C5—C6—C10	−177.1 (3)	C13—C14—C19—C18	−178.8 (2)
C2—C1—C6—C5	−0.5 (3)	C19—N2—C20—C25	−94.0 (2)
N1—C1—C6—C5	−175.0 (2)	C19—N2—C20—C21	87.5 (2)
C2—C1—C6—C10	176.9 (2)	C25—C20—C21—C22	0.4 (3)
N1—C1—C6—C10	2.4 (3)	N2—C20—C21—C22	178.9 (2)
C3—C2—C7—C8	−86.9 (3)	C25—C20—C21—C26	−179.3 (2)
C1—C2—C7—C8	92.4 (3)	N2—C20—C21—C26	−0.8 (3)
C3—C2—C7—C9	39.8 (3)	C20—C21—C22—C23	0.9 (3)
C1—C2—C7—C9	−140.9 (2)	C26—C21—C22—C23	−179.4 (3)
C5—C6—C10—C12	−67.5 (4)	C21—C22—C23—C24	−1.4 (4)
C1—C6—C10—C12	115.2 (3)	C22—C23—C24—C25	0.5 (4)
C5—C6—C10—C11	59.6 (3)	C21—C20—C25—C24	−1.2 (3)
C1—C6—C10—C11	−117.7 (3)	N2—C20—C25—C24	−179.7 (2)
C1—N1—C13—C14	177.1 (2)	C21—C20—C25—C27	177.5 (2)
N1—C13—C14—C15	−177.4 (2)	N2—C20—C25—C27	−1.0 (3)
N1—C13—C14—C19	1.0 (3)	C23—C24—C25—C20	0.8 (4)
C19—C14—C15—C16	0.0 (3)	C23—C24—C25—C27	−177.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.89 (2)	1.98 (2)	2.686 (2)	136 (2)