2,2′-[Hexane-1,6-diylbis(nitrilo­methyl­idyne)]diphenol

The title compound, C₂₀H₂₄N₂O₂, is a new potential tetra­dentate N₂O₂ Schiff base ligand which has been synthesized by the condensation reaction between hexane-1,6-diamine and salicylaldehyde, and characterized by common spectroscopic methods (FT–IR, ¹H NMR and ¹³C NMR) and CHN elemental analyses. The mol­ecule possesses crystallographically imposed C_i symmetry. Two intra­molecular O—H...N hydrogen bonds stabilize the mol­ecular conformation.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.053
• wR factor = 0.110
• Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,2'-[Hexane-1,6-diylbis(nitrilomethylidyne)]diphenol

Crystal data

C20H24N2O2	F(000) = 348
Mr = 324.41	Dx = 1.238 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 706 reflections
a = 9.3654 (12) Å	θ = 2.5–29.6°
b = 5.7915 (7) Å	µ = 0.08 mm^−1
c = 16.042 (2) Å	T = 120 K
β = 91.140 (3)°	Block, yellow
V = 869.95 (19) Å^3	0.55 × 0.40 × 0.25 mm
Z = 2

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	1433 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.056
Graphite monochromator	θmax = 28.0°, θmin = 2.2°
φ and w scans	h = −8→12
5880 measured reflections	k = −7→7
2063 independent reflections	l = −20→21

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)] = 0.053	Hydrogen site location: mixed
wR(F^2) = 0.110	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0012P)^2 + 0.515P] where P = (Fo^2 + 2Fc^2)/3
2063 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.27 e Å^−3
0 restraints	Δρmin = −0.23 e Å^−3

Special details

Experimental. ¹H NMR (Bruker AM 400, CDCl₃ with TMS as internal standard), d: 13.62 (2H, s, OH), 8.314 (2H, s, CH═N), 1.416–1.417 (12H, d, CH₂ groups) and 6.837–7.301 (8H, d, phenyl). ¹³C NMR (Bruker AM 400, CDCl₃ with TMS as internal standard), d: 26.838, 30.700, 59.346, 117.012, 118.405, 118.814, 131.111, 132.051, 161.359 and 164.600 the structure. UV–Vis spectral data (DMF as solvent): lmax = 365 nm.

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.

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

	x	y	z	Uiso*/Ueq
N1	0.40856 (12)	0.1605 (2)	0.57854 (7)	0.0330 (3)
O1	0.58801 (11)	0.49440 (19)	0.58620 (7)	0.0406 (3)
H1O	0.5006	0.4087	0.5708	0.049*
C1	0.03161 (16)	0.1125 (3)	0.48498 (11)	0.0424 (4)
H1B	−0.0430	0.2286	0.4828	0.051*
H1C	0.0654	0.0909	0.4288	0.051*
C2	0.15527 (15)	0.2017 (3)	0.54006 (11)	0.0392 (4)
H2A	0.1811	0.3555	0.5217	0.047*
H2B	0.1235	0.2134	0.5971	0.047*
C3	0.28629 (15)	0.0482 (3)	0.53794 (10)	0.0367 (4)
H3A	0.2665	−0.0963	0.5660	0.044*
H3B	0.3087	0.0136	0.4805	0.044*
C4	0.47832 (14)	0.0557 (3)	0.63635 (9)	0.0292 (3)
H4A	0.4483	−0.0892	0.6538	0.035*
C5	0.60479 (13)	0.1609 (2)	0.67540 (8)	0.0265 (3)
C6	0.65597 (15)	0.3760 (3)	0.64736 (9)	0.0302 (3)
C7	0.77993 (15)	0.4693 (3)	0.68358 (9)	0.0342 (3)
H7A	0.8148	0.6100	0.6648	0.041*
C8	0.85107 (15)	0.3532 (3)	0.74722 (9)	0.0353 (4)
H8A	0.9336	0.4164	0.7709	0.042*
C9	0.80063 (15)	0.1434 (3)	0.77610 (9)	0.0355 (4)
H9A	0.8482	0.0674	0.8195	0.043*
C10	0.67894 (15)	0.0480 (3)	0.73981 (9)	0.0315 (3)
H10A	0.6460	−0.0937	0.7587	0.038*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0257 (6)	0.0395 (7)	0.0338 (6)	−0.0030 (5)	0.0020 (5)	−0.0038 (6)
O1	0.0380 (6)	0.0394 (6)	0.0441 (6)	−0.0073 (5)	−0.0080 (5)	0.0143 (5)
C1	0.0319 (8)	0.0467 (10)	0.0485 (9)	−0.0042 (7)	−0.0046 (7)	0.0065 (8)
C2	0.0294 (8)	0.0384 (9)	0.0498 (9)	−0.0043 (7)	−0.0016 (7)	−0.0027 (7)
C3	0.0257 (7)	0.0460 (10)	0.0385 (8)	−0.0041 (7)	0.0003 (6)	−0.0107 (7)
C4	0.0243 (7)	0.0288 (8)	0.0346 (7)	−0.0015 (6)	0.0061 (5)	−0.0034 (6)
C5	0.0219 (6)	0.0266 (7)	0.0313 (7)	0.0007 (5)	0.0046 (5)	−0.0012 (6)
C6	0.0275 (7)	0.0309 (8)	0.0322 (7)	−0.0002 (6)	0.0024 (6)	0.0017 (6)
C7	0.0309 (7)	0.0317 (8)	0.0400 (8)	−0.0059 (6)	0.0014 (6)	0.0036 (6)
C8	0.0251 (7)	0.0423 (9)	0.0385 (8)	−0.0033 (6)	−0.0003 (6)	−0.0040 (7)
C9	0.0277 (7)	0.0418 (9)	0.0370 (8)	0.0048 (7)	0.0000 (6)	0.0062 (7)
C10	0.0280 (7)	0.0288 (8)	0.0380 (8)	0.0008 (6)	0.0058 (6)	0.0042 (6)

Geometric parameters (Å, º)

N1—C4	1.2769 (18)	C4—C5	1.4617 (18)
N1—C3	1.4590 (18)	C4—H4A	0.9300
O1—C6	1.3464 (17)	C5—C10	1.396 (2)
O1—H1O	0.9849	C5—C6	1.412 (2)
C1—C1^i	1.514 (3)	C6—C7	1.396 (2)
C1—C2	1.533 (2)	C7—C8	1.382 (2)
C1—H1B	0.9700	C7—H7A	0.9300
C1—H1C	0.9700	C8—C9	1.386 (2)
C2—C3	1.516 (2)	C8—H8A	0.9300
C2—H2A	0.9700	C9—C10	1.384 (2)
C2—H2B	0.9700	C9—H9A	0.9300
C3—H3A	0.9700	C10—H10A	0.9300
C3—H3B	0.9700
C4—N1—C3	119.87 (14)	N1—C4—H4A	119.6
C6—O1—H1O	107.8	C5—C4—H4A	119.6
C1^i—C1—C2	113.74 (17)	C10—C5—C6	118.81 (13)
C1^i—C1—H1B	108.8	C10—C5—C4	120.62 (13)
C2—C1—H1B	108.8	C6—C5—C4	120.56 (13)
C1^i—C1—H1C	108.8	O1—C6—C7	118.91 (13)
C2—C1—H1C	108.8	O1—C6—C5	121.53 (13)
H1B—C1—H1C	107.7	C7—C6—C5	119.56 (13)
C3—C2—C1	113.06 (14)	C8—C7—C6	120.25 (14)
C3—C2—H2A	109.0	C8—C7—H7A	119.9
C1—C2—H2A	109.0	C6—C7—H7A	119.9
C3—C2—H2B	109.0	C7—C8—C9	120.70 (14)
C1—C2—H2B	109.0	C7—C8—H8A	119.6
H2A—C2—H2B	107.8	C9—C8—H8A	119.6
N1—C3—C2	110.90 (13)	C10—C9—C8	119.48 (14)
N1—C3—H3A	109.5	C10—C9—H9A	120.3
C2—C3—H3A	109.5	C8—C9—H9A	120.3
N1—C3—H3B	109.5	C9—C10—C5	121.19 (14)
C2—C3—H3B	109.5	C9—C10—H10A	119.4
H3A—C3—H3B	108.0	C5—C10—H10A	119.4
N1—C4—C5	120.79 (14)
C1^i—C1—C2—C3	66.7 (2)	C4—C5—C6—C7	−177.70 (13)
C4—N1—C3—C2	126.97 (15)	O1—C6—C7—C8	179.19 (14)
C1—C2—C3—N1	169.59 (13)	C5—C6—C7—C8	−0.8 (2)
C3—N1—C4—C5	177.36 (12)	C6—C7—C8—C9	−0.1 (2)
N1—C4—C5—C10	178.60 (13)	C7—C8—C9—C10	1.0 (2)
N1—C4—C5—C6	−2.8 (2)	C8—C9—C10—C5	−0.9 (2)
C10—C5—C6—O1	−179.14 (13)	C6—C5—C10—C9	0.0 (2)
C4—C5—C6—O1	2.3 (2)	C4—C5—C10—C9	178.59 (13)
C10—C5—C6—C7	0.9 (2)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.98	1.68	2.5634 (16)	147