(E,E)-N,N'-Bis-(4-methoxy-benzyl-idene)cyclo-hexane-1,2-diamine.

In the title compound, C(22)H(26)N(2)O(2), the meth-oxy and the benzyl-idene groups are essentially coplanar, and the cyclo-hexane ring has a chair conformation. The two halves of the mol-ecule are related by a twofold rotation. The crystal structure is stabilized only by van der Waals inter-actions.

Related literature

For the chemistry of Schiff base derivatives, see: Negm & Zaki (2008 ▶); Feng et al. (2008 ▶); Lee & Do (2007 ▶).

Experimental

Crystal data

C22H26N2O2

M = 350.45

Orthorhombic,

a = 19.674 (3) Å

b = 5.4097 (9) Å

c = 18.662 (3) Å

V = 1986.2 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 (2) K

0.35 × 0.30 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.978, T max = 0.985

18603 measured reflections

2262 independent reflections

1588 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.154

S = 1.12

2262 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.14 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL .

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808023751/wk2089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023751/wk2089Isup2.hkl

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

C22H26N2O2	F000 = 752
Mr = 350.45	Dx = 1.172 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 3131 reflections
a = 19.674 (3) Å	θ = 3.0–27.4º
b = 5.4097 (9) Å	µ = 0.08 mm−1
c = 18.662 (3) Å	T = 298 (2) K
V = 1986.2 (6) Å3	Block, colorless
Z = 4	0.35 × 0.30 × 0.20 mm

Rigaku Mercury2 diffractometer	2262 independent reflections
Radiation source: fine-focus sealed tube	1588 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.060
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 298(2) K	θmin = 3.0º
ω scans	h = −25→25
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −7→7
Tmin = 0.978, Tmax = 0.985	l = −24→24
18603 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.4317P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2262 reflections	Δρmax = 0.13 e Å−3
118 parameters	Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
O1	0.47992 (8)	0.4625 (3)	0.41000 (8)	0.0713 (5)
N1	0.32205 (8)	0.3062 (3)	0.11039 (9)	0.0558 (5)
C5	0.36446 (9)	0.4561 (4)	0.22382 (10)	0.0493 (5)
C2	0.32123 (10)	0.3262 (5)	−0.02019 (11)	0.0629 (6)
H2A	0.3454	0.1699	−0.0204	0.075*
H2B	0.3547	0.4577	−0.0203	0.075*
C7	0.45135 (10)	0.2643 (4)	0.29659 (11)	0.0535 (5)
H7	0.4827	0.1380	0.3034	0.064*
C4	0.32303 (10)	0.4677 (4)	0.15823 (10)	0.0553 (5)
H4	0.2955	0.6057	0.1519	0.066*
C8	0.44380 (10)	0.4485 (4)	0.34762 (10)	0.0513 (5)
C6	0.41180 (10)	0.2704 (4)	0.23553 (10)	0.0539 (5)
H6	0.4170	0.1467	0.2014	0.065*
C3	0.27888 (9)	0.3439 (4)	0.04791 (10)	0.0532 (5)
H3	0.2592	0.5101	0.0506	0.064*
C10	0.35804 (10)	0.6392 (4)	0.27558 (11)	0.0591 (5)
H10	0.3270	0.7666	0.2688	0.071*
C1	0.27826 (11)	0.3452 (4)	−0.08769 (11)	0.0636 (6)
H1B	0.2587	0.5095	−0.0908	0.076*
H1A	0.3069	0.3204	−0.1294	0.076*
C11	0.52945 (14)	0.2748 (6)	0.42442 (13)	0.0871 (8)
H11A	0.5509	0.3076	0.4696	0.131*
H11B	0.5631	0.2746	0.3872	0.131*
H11C	0.5075	0.1164	0.4262	0.131*
C9	0.39688 (10)	0.6346 (4)	0.33659 (11)	0.0595 (6)
H9	0.3916	0.7580	0.3708	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0718 (9)	0.0912 (12)	0.0509 (9)	0.0097 (9)	−0.0096 (7)	−0.0121 (8)
N1	0.0534 (9)	0.0608 (11)	0.0532 (10)	0.0022 (8)	−0.0042 (8)	−0.0036 (8)
C5	0.0448 (9)	0.0533 (11)	0.0497 (11)	−0.0015 (9)	0.0020 (8)	−0.0005 (9)
C2	0.0514 (11)	0.0790 (16)	0.0583 (13)	−0.0074 (10)	0.0038 (10)	0.0038 (11)
C7	0.0538 (11)	0.0521 (12)	0.0544 (11)	0.0079 (9)	0.0001 (10)	−0.0009 (9)
C4	0.0490 (11)	0.0572 (12)	0.0597 (13)	0.0051 (9)	−0.0020 (9)	0.0010 (10)
C8	0.0510 (10)	0.0593 (12)	0.0436 (10)	−0.0043 (9)	0.0035 (9)	−0.0025 (9)
C6	0.0574 (11)	0.0524 (12)	0.0518 (11)	0.0006 (9)	0.0032 (10)	−0.0101 (9)
C3	0.0528 (11)	0.0543 (12)	0.0524 (11)	0.0028 (9)	−0.0044 (9)	0.0016 (9)
C10	0.0572 (12)	0.0541 (12)	0.0661 (13)	0.0088 (10)	0.0001 (10)	−0.0060 (10)
C1	0.0680 (13)	0.0694 (14)	0.0535 (12)	−0.0003 (11)	0.0036 (10)	0.0037 (10)
C11	0.0886 (17)	0.110 (2)	0.0625 (15)	0.0236 (16)	−0.0193 (13)	0.0001 (14)
C9	0.0628 (12)	0.0580 (13)	0.0578 (13)	0.0034 (10)	0.0017 (10)	−0.0148 (10)

O1—C8	1.366 (2)	C4—H4	0.9300
O1—C11	1.433 (3)	C8—C9	1.381 (3)
N1—C4	1.249 (2)	C6—H6	0.9300
N1—C3	1.457 (2)	C3—C3i	1.525 (4)
C5—C10	1.389 (3)	C3—H3	0.9800
C5—C6	1.387 (3)	C10—C9	1.371 (3)
C5—C4	1.472 (3)	C10—H10	0.9300
C2—C3	1.523 (3)	C1—C1i	1.516 (4)
C2—C1	1.521 (3)	C1—H1B	0.9700
C2—H2A	0.9700	C1—H1A	0.9700
C2—H2B	0.9700	C11—H11A	0.9600
C7—C6	1.380 (3)	C11—H11B	0.9600
C7—C8	1.386 (3)	C11—H11C	0.9600
C7—H7	0.9300	C9—H9	0.9300
C8—O1—C11	118.35 (17)	N1—C3—C2	109.88 (15)
C4—N1—C3	118.88 (17)	C3i—C3—C2	111.46 (14)
C10—C5—C6	117.90 (18)	N1—C3—H3	108.5
C10—C5—C4	119.83 (18)	C3i—C3—H3	108.5
C6—C5—C4	122.25 (18)	C2—C3—H3	108.5
C3—C2—C1	112.52 (16)	C9—C10—C5	120.92 (19)
C3—C2—H2A	109.1	C9—C10—H10	119.5
C1—C2—H2A	109.1	C5—C10—H10	119.5
C3—C2—H2B	109.1	C1i—C1—C2	111.22 (15)
C1—C2—H2B	109.1	C1i—C1—H1B	109.4
H2A—C2—H2B	107.8	C2—C1—H1B	109.4
C6—C7—C8	119.32 (19)	C1i—C1—H1A	109.4
C6—C7—H7	120.3	C2—C1—H1A	109.4
C8—C7—H7	120.3	H1B—C1—H1A	108.0
N1—C4—C5	124.96 (19)	O1—C11—H11A	109.5
N1—C4—H4	117.5	O1—C11—H11B	109.5
C5—C4—H4	117.5	H11A—C11—H11B	109.5
O1—C8—C9	115.75 (17)	O1—C11—H11C	109.5
O1—C8—C7	124.70 (18)	H11A—C11—H11C	109.5
C9—C8—C7	119.55 (18)	H11B—C11—H11C	109.5
C7—C6—C5	121.71 (18)	C8—C9—C10	120.61 (19)
C7—C6—H6	119.1	C8—C9—H9	119.7
C5—C6—H6	119.1	C10—C9—H9	119.7
N1—C3—C3i	109.94 (14)
C3—N1—C4—C5	−179.41 (17)	C4—N1—C3—C3i	−112.3 (2)
C10—C5—C4—N1	−175.8 (2)	C4—N1—C3—C2	124.6 (2)
C6—C5—C4—N1	6.0 (3)	C1—C2—C3—N1	175.80 (18)
C11—O1—C8—C9	−179.9 (2)	C1—C2—C3—C3i	53.7 (3)
C11—O1—C8—C7	0.1 (3)	C6—C5—C10—C9	−0.6 (3)
C6—C7—C8—O1	−179.97 (18)	C4—C5—C10—C9	−178.92 (19)
C6—C7—C8—C9	0.0 (3)	C3—C2—C1—C1i	−54.7 (3)
C8—C7—C6—C5	−0.1 (3)	O1—C8—C9—C10	179.73 (18)
C10—C5—C6—C7	0.4 (3)	C7—C8—C9—C10	−0.3 (3)
C4—C5—C6—C7	178.64 (18)	C5—C10—C9—C8	0.6 (3)