4,4',5,5'-Tetra-methyl-2,2'-[1,1'-(propane-1,3-diyldinitrilo)diethyl-idyne]diphenol.

The title Schiff base compound, C(23)H(30)N(2)O(2), has crystallographic twofold rotation symmetry. An intra-molecular O-H⋯N hydrogen bond forms a six-membered ring, producing an S(6) ring motif. The imino group is coplanar with the benzene ring. The two benzene rings are almost perpendicular to each other, making a dihedral angle of 87.38 (4)°. In the crystal structure, neighbouring mol-ecules are linked along the c axis by weak inter-molecular C-H⋯O hydrogen bonds and are further packed into columns along the b axis, forming sheets which are parallel to the bc plane.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For information on Schiff base ligands and complexes and their applications, see, for example: Fun, Kargar & Kia (2008 ▶); Fun, Kia & Kargar (2008 ▶); Fun & Kia (2008a ▶,b ▶,c ▶); Calligaris & Randaccio (1987 ▶); Casellato & Vigato (1977 ▶); For a similar structure, see: Fun & Kia (2008a ▶).

Experimental

Crystal data

C23H30N2O2

M = 366.49

Monoclinic,

a = 28.6398 (12) Å

b = 5.1264 (2) Å

c = 13.3856 (5) Å

β = 102.090 (5)°

V = 1921.67 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100.0 (1) K

0.52 × 0.18 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.959, T max = 0.997

22388 measured reflections

2955 independent reflections

2125 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.163

S = 1.09

2955 reflections

134 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808027220/at2621sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027220/at2621Isup2.hkl

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

C23H30N2O2	F000 = 792
Mr = 366.49	Dx = 1.263 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2732 reflections
a = 28.6398 (12) Å	θ = 3.1–31.1º
b = 5.1264 (2) Å	µ = 0.08 mm−1
c = 13.3856 (5) Å	T = 100.0 (1) K
β = 102.090 (5)º	Plate, yellow
V = 1921.67 (13) Å3	0.52 × 0.18 × 0.04 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2955 independent reflections
Radiation source: fine-focus sealed tube	2125 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.065
T = 100.0(1) K	θmax = 30.6º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −40→40
Tmin = 0.959, Tmax = 0.997	k = −6→7
22388 measured reflections	l = −19→19

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)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.163	w = 1/[σ2(Fo2) + (0.0692P)2 + 1.4537P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
2955 reflections	Δρmax = 0.43 e Å−3
134 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.39432 (4)	0.1912 (2)	0.79198 (8)	0.0228 (3)
N1	0.44358 (4)	0.3691 (2)	0.67166 (9)	0.0198 (3)
C1	0.37375 (5)	0.0311 (3)	0.71524 (10)	0.0186 (3)
C2	0.33866 (5)	−0.1421 (3)	0.73211 (11)	0.0202 (3)
H2A	0.3305	−0.1439	0.7958	0.024*
C3	0.31557 (5)	−0.3111 (3)	0.65766 (11)	0.0196 (3)
C4	0.32783 (5)	−0.3098 (3)	0.56081 (11)	0.0201 (3)
C5	0.36250 (5)	−0.1379 (3)	0.54410 (11)	0.0195 (3)
H5A	0.3705	−0.1376	0.4803	0.023*
C6	0.38627 (5)	0.0367 (3)	0.61851 (10)	0.0184 (3)
C7	0.42271 (5)	0.2204 (3)	0.59795 (11)	0.0193 (3)
C8	0.48072 (5)	0.5502 (3)	0.65557 (11)	0.0220 (3)
H8A	0.4677	0.6654	0.5991	0.026*
H8B	0.5067	0.4524	0.6373	0.026*
C9	0.5000	0.7123 (4)	0.7500	0.0228 (4)
C10	0.27787 (5)	−0.4945 (3)	0.67857 (12)	0.0248 (3)
H10A	0.2721	−0.4610	0.7455	0.037*
H10B	0.2885	−0.6712	0.6750	0.037*
H10C	0.2489	−0.4686	0.6285	0.037*
C11	0.30396 (6)	−0.4918 (3)	0.47727 (12)	0.0261 (3)
H11A	0.3177	−0.4684	0.4183	0.039*
H11B	0.2704	−0.4542	0.4597	0.039*
H11C	0.3086	−0.6688	0.5006	0.039*
C12	0.43456 (6)	0.2315 (4)	0.49364 (12)	0.0292 (4)
H12A	0.4686	0.2325	0.5005	0.044*
H12B	0.4213	0.3873	0.4592	0.044*
H12C	0.4213	0.0818	0.4547	0.044*
H1O1	0.4165 (8)	0.284 (5)	0.7632 (17)	0.052 (6)*
H9	0.5269 (6)	0.827 (4)	0.7343 (13)	0.028 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0254 (6)	0.0245 (6)	0.0186 (5)	−0.0057 (4)	0.0047 (4)	−0.0014 (4)
N1	0.0172 (6)	0.0191 (6)	0.0228 (6)	0.0000 (5)	0.0038 (5)	0.0027 (5)
C1	0.0181 (6)	0.0182 (7)	0.0184 (6)	0.0019 (5)	0.0014 (5)	0.0010 (5)
C2	0.0209 (7)	0.0211 (7)	0.0190 (7)	0.0013 (6)	0.0053 (5)	0.0021 (6)
C3	0.0177 (6)	0.0157 (7)	0.0246 (7)	0.0013 (5)	0.0028 (5)	0.0027 (6)
C4	0.0184 (6)	0.0173 (7)	0.0230 (7)	0.0025 (5)	0.0008 (5)	−0.0001 (6)
C5	0.0208 (7)	0.0197 (7)	0.0177 (6)	0.0036 (6)	0.0031 (5)	0.0005 (5)
C6	0.0171 (6)	0.0193 (7)	0.0185 (6)	0.0011 (5)	0.0034 (5)	0.0022 (5)
C7	0.0184 (6)	0.0195 (7)	0.0199 (7)	0.0016 (5)	0.0035 (5)	0.0031 (5)
C8	0.0200 (7)	0.0212 (7)	0.0249 (7)	−0.0008 (6)	0.0050 (6)	0.0037 (6)
C9	0.0192 (10)	0.0193 (11)	0.0297 (11)	0.000	0.0045 (8)	0.000
C10	0.0220 (7)	0.0207 (8)	0.0314 (8)	−0.0012 (6)	0.0050 (6)	0.0022 (6)
C11	0.0266 (8)	0.0222 (8)	0.0271 (8)	0.0004 (6)	−0.0001 (6)	−0.0037 (6)
C12	0.0312 (8)	0.0347 (9)	0.0232 (7)	−0.0063 (7)	0.0094 (6)	−0.0001 (7)

O1—C1	1.3497 (17)	C7—C12	1.505 (2)
O1—H1O1	0.94 (2)	C8—C9	1.5169 (19)
N1—C7	1.2904 (19)	C8—H8A	0.9700
N1—C8	1.4613 (18)	C8—H8B	0.9700
C1—C2	1.395 (2)	C9—C8i	1.5169 (19)
C1—C6	1.4143 (19)	C9—H9	1.025 (18)
C2—C3	1.380 (2)	C10—H10A	0.9600
C2—H2A	0.9300	C10—H10B	0.9600
C3—C4	1.412 (2)	C10—H10C	0.9600
C3—C10	1.501 (2)	C11—H11A	0.9600
C4—C5	1.380 (2)	C11—H11B	0.9600
C4—C11	1.506 (2)	C11—H11C	0.9600
C5—C6	1.404 (2)	C12—H12A	0.9600
C5—H5A	0.9300	C12—H12B	0.9600
C6—C7	1.474 (2)	C12—H12C	0.9600
C1—O1—H1O1	102.7 (14)	C9—C8—H8A	109.2
C7—N1—C8	119.85 (12)	N1—C8—H8B	109.2
O1—C1—C2	118.58 (12)	C9—C8—H8B	109.2
O1—C1—C6	122.04 (13)	H8A—C8—H8B	107.9
C2—C1—C6	119.38 (13)	C8—C9—C8i	113.56 (18)
C3—C2—C1	122.37 (13)	C8—C9—H9	107.5 (10)
C3—C2—H2A	118.8	C8i—C9—H9	109.0 (10)
C1—C2—H2A	118.8	C3—C10—H10A	109.5
C2—C3—C4	119.08 (13)	C3—C10—H10B	109.5
C2—C3—C10	120.86 (13)	H10A—C10—H10B	109.5
C4—C3—C10	120.06 (13)	C3—C10—H10C	109.5
C5—C4—C3	118.52 (13)	H10A—C10—H10C	109.5
C5—C4—C11	120.34 (13)	H10B—C10—H10C	109.5
C3—C4—C11	121.14 (13)	C4—C11—H11A	109.5
C4—C5—C6	123.38 (13)	C4—C11—H11B	109.5
C4—C5—H5A	118.3	H11A—C11—H11B	109.5
C6—C5—H5A	118.3	C4—C11—H11C	109.5
C5—C6—C1	117.27 (13)	H11A—C11—H11C	109.5
C5—C6—C7	122.12 (12)	H11B—C11—H11C	109.5
C1—C6—C7	120.61 (13)	C7—C12—H12A	109.5
N1—C7—C6	117.88 (12)	C7—C12—H12B	109.5
N1—C7—C12	121.89 (13)	H12A—C12—H12B	109.5
C6—C7—C12	120.22 (13)	C7—C12—H12C	109.5
N1—C8—C9	111.98 (11)	H12A—C12—H12C	109.5
N1—C8—H8A	109.2	H12B—C12—H12C	109.5
O1—C1—C2—C3	179.52 (13)	O1—C1—C6—C5	−179.81 (13)
C6—C1—C2—C3	0.3 (2)	C2—C1—C6—C5	−0.6 (2)
C1—C2—C3—C4	0.1 (2)	O1—C1—C6—C7	−0.1 (2)
C1—C2—C3—C10	−179.85 (13)	C2—C1—C6—C7	179.09 (13)
C2—C3—C4—C5	−0.2 (2)	C8—N1—C7—C6	178.61 (12)
C10—C3—C4—C5	179.74 (13)	C8—N1—C7—C12	−1.6 (2)
C2—C3—C4—C11	179.51 (13)	C5—C6—C7—N1	−178.28 (13)
C10—C3—C4—C11	−0.5 (2)	C1—C6—C7—N1	2.0 (2)
C3—C4—C5—C6	−0.1 (2)	C5—C6—C7—C12	1.9 (2)
C11—C4—C5—C6	−179.86 (13)	C1—C6—C7—C12	−177.83 (14)
C4—C5—C6—C1	0.5 (2)	C7—N1—C8—C9	178.56 (13)
C4—C5—C6—C7	−179.19 (13)	N1—C8—C9—C8i	56.33 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···N1	0.94 (3)	1.63 (2)	2.5237 (17)	157 (2)
C12—H12C···O1ii	0.96	2.57	3.466 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯N1	0.94 (3)	1.63 (2)	2.5237 (17)	157 (2)
C12—H12C⋯O1i	0.96	2.57	3.466 (2)	156

Symmetry code: (i) .