4-(Diethyl-amino)-salicyl-aldehyde azine.

The title compound, C(22)H(30)N(4)O(2), has a crystallographic inversion center located at the mid-point of the N-N single bond. Apart from the four ethyl C atoms, the non-H atoms are nearly coplanar with a mean deviation of 0.0596 (2) Å. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to (100).

Related literature

For the synthesis, see Tang et al. (2009 ▶). For a related structure, see Gil et al. (2010 ▶). For applications of photochromic aromatic Schiff base mol­ecules as mol­ecular memories and switches, see Sliwa et al. (2005 ▶).

Experimental

Crystal data

C22H30N4O2

M = 382.50

Monoclinic,

a = 8.736 (5) Å

b = 7.809 (5) Å

c = 16.122 (10) Å

β = 103.57 (2)°

V = 1069.1 (11) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 290 K

0.15 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.988, T max = 0.991

9903 measured reflections

2431 independent reflections

1227 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.228

S = 1.10

2431 reflections

129 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.45 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013237/ng5147sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013237/ng5147Isup2.hkl

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

C22H30N4O2	F(000) = 412
Mr = 382.50	Dx = 1.188 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5162 reflections
a = 8.736 (5) Å	θ = 3.1–27.7°
b = 7.809 (5) Å	µ = 0.08 mm−1
c = 16.122 (10) Å	T = 290 K
β = 103.57 (2)°	Block, yellow
V = 1069.1 (11) Å3	0.15 × 0.14 × 0.12 mm
Z = 2

Rigaku R-AXIS RAPID diffractometer	2431 independent reflections
Radiation source: fine-focus sealed tube	1227 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −11→11
Tmin = 0.988, Tmax = 0.991	k = −10→10
9903 measured reflections	l = −20→20

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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.228	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0919P)2 + 0.3133P] where P = (Fo2 + 2Fc2)/3
2431 reflections	(Δ/σ)max = 0.003
129 parameters	Δρmax = 0.45 e Å−3
1 restraint	Δρmin = −0.25 e Å−3

Experimental. (See detailed section in the paper)

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	0.2021 (2)	0.6394 (3)	0.57469 (13)	0.0809 (8)
H1	0.2663	0.6244	0.5433	0.121*
C1	0.4983 (3)	0.4599 (4)	0.60317 (18)	0.0556 (7)
H1A	0.5914	0.3972	0.6165	0.067*
C2	0.4129 (3)	0.4858 (3)	0.66828 (16)	0.0489 (7)
C3	0.4698 (3)	0.4235 (4)	0.75059 (18)	0.0602 (8)
H3	0.5638	0.3624	0.7625	0.072*
C4	0.3937 (3)	0.4480 (4)	0.81492 (18)	0.0653 (9)
H4	0.4360	0.4031	0.8688	0.078*
C5	0.2503 (3)	0.5418 (4)	0.79966 (18)	0.0575 (7)
C6	0.1898 (3)	0.5998 (4)	0.71712 (17)	0.0558 (7)
H6	0.0939	0.6573	0.7048	0.067*
C7	0.2678 (3)	0.5745 (4)	0.65257 (17)	0.0537 (7)
C8	0.2343 (5)	0.5030 (6)	0.9510 (2)	0.0878 (11)
H8A	0.3481	0.5128	0.9679	0.105*
H8B	0.1906	0.5672	0.9915	0.105*
C9	0.1893 (5)	0.3226 (6)	0.9530 (3)	0.1028 (14)
H9A	0.0770	0.3142	0.9441	0.154*
H9B	0.2387	0.2742	1.0074	0.154*
H9C	0.2226	0.2614	0.9086	0.154*
C10	0.0357 (4)	0.6857 (5)	0.8511 (2)	0.0735 (9)
H10A	0.0461	0.7776	0.8123	0.088*
H10B	0.0312	0.7373	0.9052	0.088*
C11	−0.1157 (4)	0.5939 (5)	0.8161 (2)	0.0858 (11)
H11A	−0.1144	0.5460	0.7615	0.129*
H11B	−0.2018	0.6729	0.8100	0.129*
H11C	−0.1283	0.5038	0.8545	0.129*
N1	0.4511 (3)	0.5198 (3)	0.52728 (15)	0.0589 (7)
N2	0.1766 (3)	0.5765 (4)	0.86429 (15)	0.0752 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0839 (14)	0.1066 (19)	0.0616 (13)	0.0420 (13)	0.0362 (11)	0.0333 (12)
C1	0.0554 (15)	0.0532 (17)	0.0651 (18)	0.0019 (13)	0.0280 (13)	0.0001 (13)
C2	0.0482 (14)	0.0504 (16)	0.0521 (15)	−0.0016 (12)	0.0197 (11)	0.0012 (12)
C3	0.0454 (14)	0.076 (2)	0.0619 (18)	0.0117 (13)	0.0182 (13)	0.0085 (15)
C4	0.0519 (15)	0.097 (2)	0.0484 (16)	0.0105 (16)	0.0142 (12)	0.0101 (15)
C5	0.0505 (14)	0.0707 (19)	0.0569 (17)	0.0039 (13)	0.0242 (13)	0.0042 (14)
C6	0.0525 (14)	0.0620 (18)	0.0581 (16)	0.0110 (13)	0.0235 (13)	0.0091 (14)
C7	0.0560 (15)	0.0550 (17)	0.0549 (16)	0.0075 (13)	0.0227 (13)	0.0111 (13)
C8	0.084 (2)	0.115 (3)	0.074 (2)	0.002 (2)	0.0365 (19)	−0.009 (2)
C9	0.101 (3)	0.114 (4)	0.103 (3)	0.019 (3)	0.043 (2)	0.009 (2)
C10	0.075 (2)	0.083 (2)	0.072 (2)	0.0104 (18)	0.0374 (17)	−0.0018 (17)
C11	0.079 (2)	0.091 (3)	0.094 (3)	0.009 (2)	0.0336 (19)	0.007 (2)
N1	0.0643 (14)	0.0606 (15)	0.0616 (15)	0.0027 (12)	0.0345 (11)	0.0032 (12)
N2	0.0708 (16)	0.108 (2)	0.0548 (15)	0.0222 (15)	0.0301 (12)	0.0097 (14)

O1—C7	1.351 (3)	C8—C9	1.465 (6)
O1—H1	0.8461	C8—N2	1.486 (4)
C1—N1	1.284 (4)	C8—H8A	0.9700
C1—C2	1.438 (4)	C8—H8B	0.9700
C1—H1A	0.9300	C9—H9A	0.9600
C2—C3	1.391 (4)	C9—H9B	0.9600
C2—C7	1.414 (4)	C9—H9C	0.9600
C3—C4	1.371 (4)	C10—N2	1.471 (4)
C3—H3	0.9300	C10—C11	1.494 (5)
C4—C5	1.422 (4)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—N2	1.374 (3)	C11—H11A	0.9600
C5—C6	1.387 (4)	C11—H11B	0.9600
C6—C7	1.386 (3)	C11—H11C	0.9600
C6—H6	0.9300	N1—N1i	1.397 (4)
C7—O1—H1	107.9	C9—C8—H8B	109.4
N1—C1—C2	122.6 (3)	N2—C8—H8B	109.4
N1—C1—H1A	118.7	H8A—C8—H8B	108.0
C2—C1—H1A	118.7	C8—C9—H9A	109.5
C3—C2—C7	116.6 (2)	C8—C9—H9B	109.5
C3—C2—C1	121.1 (2)	H9A—C9—H9B	109.5
C7—C2—C1	122.3 (2)	C8—C9—H9C	109.5
C4—C3—C2	123.0 (3)	H9A—C9—H9C	109.5
C4—C3—H3	118.5	H9B—C9—H9C	109.5
C2—C3—H3	118.5	N2—C10—C11	114.4 (3)
C3—C4—C5	120.3 (3)	N2—C10—H10A	108.7
C3—C4—H4	119.8	C11—C10—H10A	108.7
C5—C4—H4	119.8	N2—C10—H10B	108.7
N2—C5—C6	121.5 (2)	C11—C10—H10B	108.7
N2—C5—C4	121.4 (3)	H10A—C10—H10B	107.6
C6—C5—C4	117.1 (2)	C10—C11—H11A	109.5
C7—C6—C5	122.0 (2)	C10—C11—H11B	109.5
C7—C6—H6	119.0	H11A—C11—H11B	109.5
C5—C6—H6	119.0	C10—C11—H11C	109.5
O1—C7—C6	117.9 (2)	H11A—C11—H11C	109.5
O1—C7—C2	121.2 (2)	H11B—C11—H11C	109.5
C6—C7—C2	120.9 (2)	C1—N1—N1i	114.3 (3)
C9—C8—N2	111.0 (3)	C5—N2—C10	122.0 (2)
C9—C8—H8A	109.4	C5—N2—C8	121.4 (3)
N2—C8—H8A	109.4	C10—N2—C8	116.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ii	0.97	2.64	3.481 (5)	145
O1—H1···N1	0.85	1.88	2.640 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1i	0.97	2.64	3.481 (5)	145
O1—H1⋯N1	0.85	1.88	2.640 (3)	149

Symmetry code: (i) .