Download citation
Download citation
link to html
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 Ci symmetry. Two intra­molecular O—H...N hydrogen bonds stabilize the mol­ecular conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028157/rz2056sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028157/rz2056Isup2.hkl
Contains datablock I

CCDC reference: 288853

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C20H24N2O2F(000) = 348
Mr = 324.41Dx = 1.238 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 706 reflections
a = 9.3654 (12) Åθ = 2.5–29.6°
b = 5.7915 (7) ŵ = 0.08 mm1
c = 16.042 (2) ÅT = 120 K
β = 91.140 (3)°Block, yellow
V = 869.95 (19) Å30.55 × 0.40 × 0.25 mm
Z = 2
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
1433 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.056
Graphite monochromatorθmax = 28.0°, θmin = 2.2°
φ and w scansh = 812
5880 measured reflectionsk = 77
2063 independent reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: mixed
wR(F2) = 0.110H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0012P)2 + 0.515P]
where P = (Fo2 + 2Fc2)/3
2063 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.23 e Å3
Special details top

Experimental. 1H NMR (Bruker AM 400, CDCl3 with TMS as internal standard), d: 13.62 (2H, s, OH), 8.314 (2H, s, CHN), 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 (Å2) top
xyzUiso*/Ueq
N10.40856 (12)0.1605 (2)0.57854 (7)0.0330 (3)
O10.58801 (11)0.49440 (19)0.58620 (7)0.0406 (3)
H1O0.50060.40870.57080.049*
C10.03161 (16)0.1125 (3)0.48498 (11)0.0424 (4)
H1B0.04300.22860.48280.051*
H1C0.06540.09090.42880.051*
C20.15527 (15)0.2017 (3)0.54006 (11)0.0392 (4)
H2A0.18110.35550.52170.047*
H2B0.12350.21340.59710.047*
C30.28629 (15)0.0482 (3)0.53794 (10)0.0367 (4)
H3A0.26650.09630.56600.044*
H3B0.30870.01360.48050.044*
C40.47832 (14)0.0557 (3)0.63635 (9)0.0292 (3)
H4A0.44830.08920.65380.035*
C50.60479 (13)0.1609 (2)0.67540 (8)0.0265 (3)
C60.65597 (15)0.3760 (3)0.64736 (9)0.0302 (3)
C70.77993 (15)0.4693 (3)0.68358 (9)0.0342 (3)
H7A0.81480.61000.66480.041*
C80.85107 (15)0.3532 (3)0.74722 (9)0.0353 (4)
H8A0.93360.41640.77090.042*
C90.80063 (15)0.1434 (3)0.77610 (9)0.0355 (4)
H9A0.84820.06740.81950.043*
C100.67894 (15)0.0480 (3)0.73981 (9)0.0315 (3)
H10A0.64600.09370.75870.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0257 (6)0.0395 (7)0.0338 (6)0.0030 (5)0.0020 (5)0.0038 (6)
O10.0380 (6)0.0394 (6)0.0441 (6)0.0073 (5)0.0080 (5)0.0143 (5)
C10.0319 (8)0.0467 (10)0.0485 (9)0.0042 (7)0.0046 (7)0.0065 (8)
C20.0294 (8)0.0384 (9)0.0498 (9)0.0043 (7)0.0016 (7)0.0027 (7)
C30.0257 (7)0.0460 (10)0.0385 (8)0.0041 (7)0.0003 (6)0.0107 (7)
C40.0243 (7)0.0288 (8)0.0346 (7)0.0015 (6)0.0061 (5)0.0034 (6)
C50.0219 (6)0.0266 (7)0.0313 (7)0.0007 (5)0.0046 (5)0.0012 (6)
C60.0275 (7)0.0309 (8)0.0322 (7)0.0002 (6)0.0024 (6)0.0017 (6)
C70.0309 (7)0.0317 (8)0.0400 (8)0.0059 (6)0.0014 (6)0.0036 (6)
C80.0251 (7)0.0423 (9)0.0385 (8)0.0033 (6)0.0003 (6)0.0040 (7)
C90.0277 (7)0.0418 (9)0.0370 (8)0.0048 (7)0.0000 (6)0.0062 (7)
C100.0280 (7)0.0288 (8)0.0380 (8)0.0008 (6)0.0058 (6)0.0042 (6)
Geometric parameters (Å, º) top
N1—C41.2769 (18)C4—C51.4617 (18)
N1—C31.4590 (18)C4—H4A0.9300
O1—C61.3464 (17)C5—C101.396 (2)
O1—H1O0.9849C5—C61.412 (2)
C1—C1i1.514 (3)C6—C71.396 (2)
C1—C21.533 (2)C7—C81.382 (2)
C1—H1B0.9700C7—H7A0.9300
C1—H1C0.9700C8—C91.386 (2)
C2—C31.516 (2)C8—H8A0.9300
C2—H2A0.9700C9—C101.384 (2)
C2—H2B0.9700C9—H9A0.9300
C3—H3A0.9700C10—H10A0.9300
C3—H3B0.9700
C4—N1—C3119.87 (14)N1—C4—H4A119.6
C6—O1—H1O107.8C5—C4—H4A119.6
C1i—C1—C2113.74 (17)C10—C5—C6118.81 (13)
C1i—C1—H1B108.8C10—C5—C4120.62 (13)
C2—C1—H1B108.8C6—C5—C4120.56 (13)
C1i—C1—H1C108.8O1—C6—C7118.91 (13)
C2—C1—H1C108.8O1—C6—C5121.53 (13)
H1B—C1—H1C107.7C7—C6—C5119.56 (13)
C3—C2—C1113.06 (14)C8—C7—C6120.25 (14)
C3—C2—H2A109.0C8—C7—H7A119.9
C1—C2—H2A109.0C6—C7—H7A119.9
C3—C2—H2B109.0C7—C8—C9120.70 (14)
C1—C2—H2B109.0C7—C8—H8A119.6
H2A—C2—H2B107.8C9—C8—H8A119.6
N1—C3—C2110.90 (13)C10—C9—C8119.48 (14)
N1—C3—H3A109.5C10—C9—H9A120.3
C2—C3—H3A109.5C8—C9—H9A120.3
N1—C3—H3B109.5C9—C10—C5121.19 (14)
C2—C3—H3B109.5C9—C10—H10A119.4
H3A—C3—H3B108.0C5—C10—H10A119.4
N1—C4—C5120.79 (14)
C1i—C1—C2—C366.7 (2)C4—C5—C6—C7177.70 (13)
C4—N1—C3—C2126.97 (15)O1—C6—C7—C8179.19 (14)
C1—C2—C3—N1169.59 (13)C5—C6—C7—C80.8 (2)
C3—N1—C4—C5177.36 (12)C6—C7—C8—C90.1 (2)
N1—C4—C5—C10178.60 (13)C7—C8—C9—C101.0 (2)
N1—C4—C5—C62.8 (2)C8—C9—C10—C50.9 (2)
C10—C5—C6—O1179.14 (13)C6—C5—C10—C90.0 (2)
C4—C5—C6—O12.3 (2)C4—C5—C10—C9178.59 (13)
C10—C5—C6—C70.9 (2)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N10.981.682.5634 (16)147
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds