N,N'-Bis(2,3-dimeth-oxy-benzyl-idene)ethane-1,2-diamine.

The title compound, C(20)H(24)N(2)O(4), crystallizes with two half (centrosymmetric) mol-ecules in the asymmetric unit. There are only minor differences between the geometric parameters between these two mol-ecules. The two aromatic rings in both mol-ecules are mutually coplanar.

Related literature

For general background to the properties of Schiff bases, see: Layer (1963 ▶); Chen et al. (2008 ▶); May et al. (2004 ▶). For related structures, see: Harada et al. (2004 ▶); Tariq et al. (2010 ▶).

Experimental

Crystal data

C20H24N2O4

M = 356.41

Triclinic,

a = 5.0491 (5) Å

b = 13.5803 (15) Å

c = 13.5803 (15) Å

α = 89.866 (2)°

β = 88.863 (1)°

γ = 88.863 (1)°

V = 930.81 (17) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.47 × 0.41 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.965

4767 measured reflections

3207 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.184

S = 1.04

3207 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536811033423/bt5615sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033423/bt5615Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033423/bt5615Isup3.cml

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

C20H24N2O4	Z = 2
Mr = 356.41	F(000) = 380
Triclinic, P1	Dx = 1.272 Mg m−3
a = 5.0491 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.5803 (15) Å	Cell parameters from 1477 reflections
c = 13.5803 (15) Å	θ = 3.0–25.3°
α = 89.866 (2)°	µ = 0.09 mm−1
β = 88.863 (1)°	T = 298 K
γ = 88.863 (1)°	Block, colorless
V = 930.81 (17) Å3	0.47 × 0.41 × 0.40 mm

Bruker SMART CCD area-detector diffractometer	3207 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.959, Tmax = 0.965	k = −11→16
4767 measured reflections	l = −16→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.087P)2 + 0.1177P] where P = (Fo2 + 2Fc2)/3
3207 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.26 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
N1	0.8830 (5)	0.89133 (19)	0.93288 (19)	0.0473 (7)
N2	−0.3832 (5)	0.39082 (19)	0.56712 (18)	0.0465 (7)
O1	0.3838 (4)	0.91237 (15)	0.70797 (15)	0.0485 (6)
O2	0.0726 (4)	0.76450 (16)	0.65165 (16)	0.0531 (6)
O3	0.1160 (4)	0.41215 (15)	0.79204 (15)	0.0485 (6)
O4	0.4260 (4)	0.26460 (16)	0.84843 (16)	0.0530 (6)
C1	0.7533 (6)	0.8916 (2)	0.8551 (2)	0.0412 (8)
H1	0.7668	0.9451	0.8126	0.049*
C2	0.5804 (6)	0.8102 (2)	0.8286 (2)	0.0382 (7)
C3	0.4037 (6)	0.8220 (2)	0.7529 (2)	0.0376 (7)
C4	0.2413 (6)	0.7449 (2)	0.7263 (2)	0.0403 (8)
C5	0.2564 (7)	0.6562 (2)	0.7739 (2)	0.0476 (9)
H5	0.1496	0.6046	0.7557	0.057*
C6	0.4331 (7)	0.6448 (2)	0.8495 (2)	0.0536 (9)
H6	0.4449	0.5848	0.8825	0.064*
C7	0.5912 (7)	0.7204 (2)	0.8764 (2)	0.0486 (9)
H7	0.7080	0.7111	0.9279	0.058*
C8	0.5069 (9)	0.9172 (3)	0.6126 (3)	0.0718 (12)
H8A	0.6926	0.9019	0.6176	0.108*
H8B	0.4839	0.9824	0.5862	0.108*
H8C	0.4270	0.8706	0.5698	0.108*
C9	−0.0886 (7)	0.6865 (3)	0.6191 (3)	0.0581 (10)
H9A	0.0225	0.6333	0.5948	0.087*
H9B	−0.2003	0.7100	0.5673	0.087*
H9C	−0.1965	0.6636	0.6731	0.087*
C10	1.0447 (6)	0.9765 (2)	0.9517 (2)	0.0475 (8)
H10A	1.0266	1.0238	0.8985	0.057*
H10B	1.2296	0.9563	0.9550	0.057*
C11	−0.2531 (6)	0.3919 (2)	0.6447 (2)	0.0401 (8)
H11	−0.2679	0.4464	0.6860	0.048*
C12	−0.0791 (6)	0.3099 (2)	0.6716 (2)	0.0371 (7)
C13	0.0954 (6)	0.3223 (2)	0.7471 (2)	0.0366 (7)
C14	0.2596 (6)	0.2440 (2)	0.7735 (2)	0.0410 (8)
C15	0.2442 (7)	0.1563 (2)	0.7261 (2)	0.0476 (8)
H15	0.3533	0.1038	0.7447	0.057*
C16	0.0680 (7)	0.1443 (2)	0.6506 (2)	0.0542 (9)
H16	0.0591	0.0840	0.6187	0.065*
C17	−0.0920 (7)	0.2208 (2)	0.6233 (2)	0.0478 (8)
H17	−0.2097	0.2131	0.5722	0.057*
C18	−0.0072 (9)	0.4175 (3)	0.8874 (3)	0.0732 (12)
H18A	−0.1927	0.4047	0.8823	0.110*
H18B	0.0152	0.4820	0.9143	0.110*
H18C	0.0731	0.3693	0.9298	0.110*
C19	0.5896 (7)	0.1861 (3)	0.8810 (3)	0.0576 (10)
H19A	0.4812	0.1339	0.9058	0.086*
H19B	0.7008	0.2088	0.9324	0.086*
H19C	0.6979	0.1621	0.8270	0.086*
C20	−0.5456 (6)	0.4766 (2)	0.5481 (2)	0.0466 (8)
H20A	−0.5313	0.5233	0.6015	0.056*
H20B	−0.7296	0.4581	0.5437	0.056*

	U11	U22	U33	U12	U13	U23
N1	0.0444 (17)	0.0526 (17)	0.0455 (16)	−0.0109 (13)	−0.0038 (13)	−0.0035 (12)
N2	0.0435 (17)	0.0508 (17)	0.0450 (16)	0.0084 (13)	−0.0041 (13)	0.0012 (12)
O1	0.0537 (15)	0.0412 (13)	0.0506 (14)	0.0013 (10)	−0.0041 (11)	0.0001 (10)
O2	0.0421 (14)	0.0577 (15)	0.0600 (14)	−0.0042 (11)	−0.0126 (11)	−0.0077 (11)
O3	0.0510 (14)	0.0437 (13)	0.0511 (14)	−0.0042 (11)	−0.0052 (11)	0.0006 (10)
O4	0.0422 (14)	0.0563 (15)	0.0609 (14)	0.0030 (11)	−0.0122 (11)	0.0088 (11)
C1	0.0410 (19)	0.0426 (18)	0.0399 (18)	−0.0035 (15)	0.0031 (15)	−0.0032 (14)
C2	0.0334 (18)	0.0415 (18)	0.0396 (17)	−0.0047 (14)	0.0039 (14)	−0.0055 (14)
C3	0.0364 (18)	0.0353 (18)	0.0410 (17)	−0.0004 (14)	0.0047 (14)	−0.0043 (13)
C4	0.0312 (18)	0.0459 (19)	0.0435 (18)	0.0001 (15)	0.0026 (15)	−0.0100 (14)
C5	0.039 (2)	0.044 (2)	0.060 (2)	−0.0077 (15)	0.0030 (17)	−0.0073 (16)
C6	0.057 (2)	0.046 (2)	0.059 (2)	−0.0063 (17)	−0.0039 (18)	0.0084 (16)
C7	0.049 (2)	0.052 (2)	0.0447 (19)	−0.0042 (17)	−0.0054 (16)	0.0007 (15)
C8	0.092 (3)	0.066 (3)	0.058 (2)	0.000 (2)	0.003 (2)	0.0093 (19)
C9	0.037 (2)	0.070 (2)	0.068 (2)	−0.0042 (18)	−0.0082 (18)	−0.0223 (19)
C10	0.0351 (19)	0.058 (2)	0.0502 (19)	−0.0087 (16)	−0.0039 (15)	0.0004 (15)
C11	0.0389 (19)	0.0429 (18)	0.0385 (18)	0.0000 (15)	0.0017 (15)	0.0005 (13)
C12	0.0324 (17)	0.0377 (18)	0.0410 (17)	0.0000 (14)	0.0023 (14)	0.0037 (13)
C13	0.0334 (18)	0.0347 (17)	0.0415 (17)	−0.0036 (14)	0.0025 (14)	0.0021 (13)
C14	0.0335 (18)	0.0439 (19)	0.0452 (19)	−0.0010 (15)	0.0033 (15)	0.0102 (15)
C15	0.042 (2)	0.044 (2)	0.056 (2)	0.0040 (15)	0.0024 (17)	0.0040 (16)
C16	0.059 (2)	0.041 (2)	0.062 (2)	0.0030 (17)	0.0016 (19)	−0.0088 (16)
C17	0.046 (2)	0.051 (2)	0.0466 (19)	0.0015 (17)	−0.0048 (16)	−0.0036 (15)
C18	0.095 (3)	0.065 (3)	0.059 (2)	0.002 (2)	0.004 (2)	−0.0108 (19)
C19	0.040 (2)	0.063 (2)	0.071 (2)	0.0084 (17)	−0.0075 (18)	0.0232 (18)
C20	0.0361 (19)	0.056 (2)	0.0472 (18)	0.0086 (16)	−0.0053 (15)	−0.0002 (15)

N1—C1	1.254 (4)	C9—H9A	0.9600
N1—C10	1.455 (4)	C9—H9B	0.9600
N2—C11	1.253 (4)	C9—H9C	0.9600
N2—C20	1.437 (4)	C10—C10i	1.517 (6)
O1—C3	1.372 (3)	C10—H10A	0.9700
O1—C8	1.428 (4)	C10—H10B	0.9700
O2—C4	1.360 (4)	C11—C12	1.456 (4)
O2—C9	1.425 (4)	C11—H11	0.9300
O3—C13	1.373 (3)	C12—C13	1.378 (4)
O3—C18	1.427 (4)	C12—C17	1.381 (4)
O4—C14	1.366 (4)	C13—C14	1.386 (4)
O4—C19	1.411 (4)	C14—C15	1.359 (4)
C1—C2	1.472 (4)	C15—C16	1.382 (5)
C1—H1	0.9300	C15—H15	0.9300
C2—C7	1.381 (4)	C16—C17	1.359 (4)
C2—C3	1.381 (4)	C16—H16	0.9300
C3—C4	1.395 (4)	C17—H17	0.9300
C4—C5	1.367 (4)	C18—H18A	0.9600
C5—C6	1.379 (4)	C18—H18B	0.9600
C5—H5	0.9300	C18—H18C	0.9600
C6—C7	1.368 (4)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—H7	0.9300	C19—H19C	0.9600
C8—H8A	0.9600	C20—C20ii	1.518 (6)
C8—H8B	0.9600	C20—H20A	0.9700
C8—H8C	0.9600	C20—H20B	0.9700
C1—N1—C10	117.4 (3)	N1—C10—H10B	109.8
C11—N2—C20	116.3 (3)	C10i—C10—H10B	109.8
C3—O1—C8	114.6 (2)	H10A—C10—H10B	108.3
C4—O2—C9	117.7 (3)	N2—C11—C12	121.4 (3)
C13—O3—C18	114.0 (2)	N2—C11—H11	119.3
C14—O4—C19	116.3 (3)	C12—C11—H11	119.3
N1—C1—C2	122.3 (3)	C13—C12—C17	120.7 (3)
N1—C1—H1	118.8	C13—C12—C11	118.8 (3)
C2—C1—H1	118.8	C17—C12—C11	120.5 (3)
C7—C2—C3	118.1 (3)	O3—C13—C12	120.5 (3)
C7—C2—C1	121.9 (3)	O3—C13—C14	120.4 (3)
C3—C2—C1	119.9 (3)	C12—C13—C14	118.9 (3)
O1—C3—C2	118.4 (3)	C15—C14—O4	125.9 (3)
O1—C3—C4	121.1 (3)	C15—C14—C13	120.0 (3)
C2—C3—C4	120.4 (3)	O4—C14—C13	114.1 (3)
O2—C4—C5	123.6 (3)	C14—C15—C16	120.8 (3)
O2—C4—C3	115.8 (3)	C14—C15—H15	119.6
C5—C4—C3	120.6 (3)	C16—C15—H15	119.6
C4—C5—C6	118.7 (3)	C17—C16—C15	119.8 (3)
C4—C5—H5	120.6	C17—C16—H16	120.1
C6—C5—H5	120.6	C15—C16—H16	120.1
C7—C6—C5	120.9 (3)	C16—C17—C12	119.8 (3)
C7—C6—H6	119.5	C16—C17—H17	120.1
C5—C6—H6	119.5	C12—C17—H17	120.1
C6—C7—C2	121.2 (3)	O3—C18—H18A	109.5
C6—C7—H7	119.4	O3—C18—H18B	109.5
C2—C7—H7	119.4	H18A—C18—H18B	109.5
O1—C8—H8A	109.5	O3—C18—H18C	109.5
O1—C8—H8B	109.5	H18A—C18—H18C	109.5
H8A—C8—H8B	109.5	H18B—C18—H18C	109.5
O1—C8—H8C	109.5	O4—C19—H19A	109.5
H8A—C8—H8C	109.5	O4—C19—H19B	109.5
H8B—C8—H8C	109.5	H19A—C19—H19B	109.5
O2—C9—H9A	109.5	O4—C19—H19C	109.5
O2—C9—H9B	109.5	H19A—C19—H19C	109.5
H9A—C9—H9B	109.5	H19B—C19—H19C	109.5
O2—C9—H9C	109.5	N2—C20—C20ii	109.2 (3)
H9A—C9—H9C	109.5	N2—C20—H20A	109.8
H9B—C9—H9C	109.5	C20ii—C20—H20A	109.8
N1—C10—C10i	109.3 (3)	N2—C20—H20B	109.8
N1—C10—H10A	109.8	C20ii—C20—H20B	109.8
C10i—C10—H10A	109.8	H20A—C20—H20B	108.3
C10—N1—C1—C2	−179.3 (3)	C20—N2—C11—C12	−179.3 (3)
N1—C1—C2—C7	−13.6 (5)	N2—C11—C12—C13	168.0 (3)
N1—C1—C2—C3	167.5 (3)	N2—C11—C12—C17	−13.0 (5)
C8—O1—C3—C2	105.0 (3)	C18—O3—C13—C12	104.8 (3)
C8—O1—C3—C4	−78.0 (4)	C18—O3—C13—C14	−78.6 (4)
C7—C2—C3—O1	177.2 (3)	C17—C12—C13—O3	177.1 (3)
C1—C2—C3—O1	−3.8 (4)	C11—C12—C13—O3	−4.0 (4)
C7—C2—C3—C4	0.2 (4)	C17—C12—C13—C14	0.5 (4)
C1—C2—C3—C4	179.2 (3)	C11—C12—C13—C14	179.4 (3)
C9—O2—C4—C5	−2.7 (4)	C19—O4—C14—C15	−2.2 (4)
C9—O2—C4—C3	177.2 (3)	C19—O4—C14—C13	177.4 (3)
O1—C3—C4—O2	2.4 (4)	O3—C13—C14—C15	−177.6 (3)
C2—C3—C4—O2	179.3 (2)	C12—C13—C14—C15	−1.0 (4)
O1—C3—C4—C5	−177.7 (3)	O3—C13—C14—O4	2.8 (4)
C2—C3—C4—C5	−0.8 (4)	C12—C13—C14—O4	179.4 (2)
O2—C4—C5—C6	−179.3 (3)	O4—C14—C15—C16	−179.7 (3)
C3—C4—C5—C6	0.8 (4)	C13—C14—C15—C16	0.8 (5)
C4—C5—C6—C7	−0.2 (5)	C14—C15—C16—C17	0.0 (5)
C5—C6—C7—C2	−0.4 (5)	C15—C16—C17—C12	−0.5 (5)
C3—C2—C7—C6	0.4 (5)	C13—C12—C17—C16	0.3 (5)
C1—C2—C7—C6	−178.6 (3)	C11—C12—C17—C16	−178.6 (3)
C1—N1—C10—C10i	120.9 (4)	C11—N2—C20—C20ii	119.1 (4)