Literature DB >> 21578365

5,5'-Dimeth-oxy-2,2'-[(nonane-1,9-diyldi-oxy)bis-(nitrilo-methyl-idyne)]diphenol.

Li Li, Hong-Zheng Ma, Su-Xia Gao, Wen-Kui Dong, Jian-Chao Wu.   

Abstract

The mol-ecule of the title compound, C(25)H(34)N(2)O(6), adopts a fully extended configuration. The oxime (-CH=N-O-) group is coplanar with the aromatic ring and the two benzene rings are almost parallel, making a dihedral angle of 0.16 (3)°. In the crystal structure, strong intra-molecular O-H⋯N hydrogen bonds generate six-membered S(6) ring motifs. Inter-molecular C-H⋯O hydrogen bonds link each mol-ecule to five others, forming an infinite three-dimensional supra-molecular structure. The crystal is further stabilized by π-π stacking inter-actions between neighbouring benzene rings [centroid-centroid distance = 3.744 (2) Å].

Entities:  

Year:  2009        PMID： 21578365      PMCID： PMC2971058          DOI： 10.1107/S1600536809041038

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Bernstein et al. (1995 ▶); Campbell et al. (2001 ▶); Desiraju (1996 ▶); Dong, He, Guan et al. (2008 ▶); Dong, He, Li et al. (2008 ▶); Dong, Li et al. (2008 ▶); Dong et al. (2009 ▶); Mohand et al. (1995 ▶); Sun et al. (2009 ▶).

Experimental

Crystal data

C25H34N2O6 M = 458.54 Triclinic, a = 10.4701 (10) Å b = 11.1249 (12) Å c = 12.7602 (14) Å α = 65.544 (1)° β = 86.664 (2)° γ = 67.085 (1)° V = 1236.7 (2) Å3 Z = 2 Mo Kα radiation μ = 0.09 mm−1 T = 298 K 0.48 × 0.46 × 0.21 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.959, T max = 0.982 6463 measured reflections 4303 independent reflections 2050 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.049 wR(F 2) = 0.125 S = 1.05 4303 reflections 300 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.18 e Å−3 Data collection: SMART (Siemens, 1996 ▶); cell refinement: SMART; data reduction: SAINT (Siemens, 1996 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536809041038/hg2576sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041038/hg2576Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C25H34N2O6Z = 2
Mr = 458.54F(000) = 492
Triclinic, P1Dx = 1.231 Mg m−3
Hall symbol: -P 1Melting point = 465–467 K
a = 10.4701 (10) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1249 (12) ÅCell parameters from 1465 reflections
c = 12.7602 (14) Åθ = 2.2–22.6°
α = 65.544 (1)°µ = 0.09 mm−1
β = 86.664 (2)°T = 298 K
γ = 67.085 (1)°Block-like, colorless
V = 1236.7 (2) Å30.48 × 0.46 × 0.21 mm
Bruker SMART 1000 CCD area-detector diffractometer4303 independent reflections
Radiation source: fine-focus sealed tube2050 reflections with I > 2σ(I)
graphiteRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.959, Tmax = 0.982k = −13→13
6463 measured reflectionsl = −9→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0355P)2] where P = (Fo2 + 2Fc2)/3
4303 reflections(Δ/σ)max < 0.001
300 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.18 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.
xyzUiso*/Ueq
N10.2659 (2)−0.4795 (2)0.60645 (19)0.0660 (6)
N20.7314 (2)0.4634 (2)0.87062 (18)0.0634 (6)
O10.34859 (18)−0.40335 (19)0.59502 (16)0.0766 (6)
O20.72925 (18)0.37983 (19)0.81319 (15)0.0766 (6)
O30.07937 (17)−0.58178 (17)0.68503 (15)0.0769 (6)
H30.1269−0.53620.67940.115*
O40.02223 (19)−0.88667 (18)0.53611 (16)0.0767 (6)
O50.67807 (19)0.59846 (18)1.00861 (15)0.0830 (6)
H50.66990.54720.98050.124*
O60.9436 (2)0.87142 (19)0.98147 (17)0.0857 (6)
C10.3053 (3)−0.3278 (3)0.6680 (2)0.0719 (8)
H1A0.3108−0.39480.74780.086*
H1B0.2098−0.25670.64220.086*
C20.4015 (3)−0.2568 (3)0.6585 (2)0.0746 (8)
H2A0.3948−0.19200.57770.089*
H2B0.4963−0.33010.68130.089*
C30.3762 (3)−0.1723 (3)0.7304 (2)0.0681 (8)
H3A0.2810−0.09990.70970.082*
H3B0.3871−0.23690.81190.082*
C40.4758 (2)−0.0993 (3)0.7122 (2)0.0659 (7)
H4A0.5705−0.17270.73370.079*
H4B0.4661−0.03740.63020.079*
C50.4563 (2)−0.0103 (2)0.7788 (2)0.0656 (7)
H5A0.4717−0.07270.86120.079*
H5B0.36050.06060.76050.079*
C60.5536 (3)0.0667 (2)0.7526 (2)0.0660 (7)
H6A0.6491−0.00450.76890.079*
H6B0.53670.13000.67030.079*
C70.5397 (3)0.1549 (3)0.8196 (2)0.0695 (8)
H7A0.55730.09220.90190.083*
H7B0.44460.22690.80320.083*
C80.6393 (3)0.2293 (3)0.7898 (2)0.0715 (8)
H8A0.73370.15680.80350.086*
H8B0.61960.29320.70760.086*
C90.6336 (3)0.3152 (3)0.8561 (2)0.0728 (8)
H9A0.54010.38850.84450.087*
H9B0.65940.25280.93840.087*
C100.2957 (2)−0.5469 (3)0.5419 (2)0.0622 (7)
H100.3658−0.54070.49430.075*
C110.2216 (2)−0.6325 (2)0.5424 (2)0.0525 (6)
C120.1170 (2)−0.6471 (2)0.6125 (2)0.0510 (6)
C130.0470 (2)−0.7291 (2)0.6116 (2)0.0565 (7)
H13−0.0242−0.73590.65780.068*
C140.0836 (3)−0.8008 (2)0.5414 (2)0.0566 (7)
C150.1875 (3)−0.7888 (3)0.4717 (2)0.0669 (8)
H150.2120−0.83710.42430.080*
C160.2542 (3)−0.7060 (3)0.4726 (2)0.0656 (7)
H160.3239−0.69830.42480.079*
C17−0.0791 (3)−0.9095 (3)0.6107 (2)0.0883 (9)
H17A−0.0392−0.94930.68970.132*
H17B−0.1096−0.97550.60060.132*
H17C−0.1575−0.81940.59270.132*
C180.8248 (3)0.5120 (2)0.8369 (2)0.0580 (7)
H180.87920.48710.78290.070*
C190.8512 (2)0.6043 (2)0.8781 (2)0.0511 (6)
C200.7786 (2)0.6443 (3)0.9615 (2)0.0573 (7)
C210.8074 (3)0.7331 (3)0.9981 (2)0.0632 (7)
H210.75820.75941.05370.076*
C220.9084 (3)0.7820 (3)0.9523 (2)0.0606 (7)
C230.9834 (3)0.7427 (3)0.8705 (2)0.0670 (8)
H231.05320.77480.84050.080*
C240.9532 (3)0.6557 (2)0.8348 (2)0.0617 (7)
H241.00300.63010.77920.074*
C250.8799 (3)0.9062 (3)1.0714 (3)0.1070 (12)
H25A0.78060.95551.04990.161*
H25B0.91510.96731.08420.161*
H25C0.90050.81931.14120.161*
U11U22U33U12U13U23
N10.0605 (15)0.0674 (15)0.0816 (16)−0.0295 (13)0.0040 (13)−0.0379 (14)
N20.0647 (15)0.0654 (14)0.0738 (15)−0.0312 (13)0.0088 (13)−0.0376 (13)
O10.0729 (13)0.0867 (13)0.0998 (14)−0.0434 (11)0.0196 (11)−0.0570 (12)
O20.0791 (13)0.0933 (14)0.0953 (14)−0.0536 (12)0.0278 (12)−0.0592 (12)
O30.0862 (13)0.0910 (13)0.0914 (13)−0.0466 (11)0.0382 (12)−0.0665 (12)
O40.0870 (14)0.0836 (14)0.0873 (14)−0.0448 (12)0.0190 (12)−0.0527 (12)
O50.0860 (14)0.1028 (15)0.0933 (14)−0.0538 (12)0.0403 (12)−0.0610 (12)
O60.1094 (16)0.0787 (13)0.0937 (15)−0.0487 (13)0.0137 (13)−0.0494 (12)
C10.0660 (19)0.0783 (19)0.088 (2)−0.0345 (16)0.0122 (17)−0.0460 (18)
C20.0654 (19)0.0794 (19)0.093 (2)−0.0348 (17)0.0070 (17)−0.0434 (18)
C30.0597 (18)0.0706 (18)0.084 (2)−0.0268 (16)0.0026 (16)−0.0405 (17)
C40.0593 (18)0.0659 (18)0.0772 (19)−0.0237 (15)−0.0022 (16)−0.0347 (16)
C50.0592 (17)0.0637 (17)0.0777 (19)−0.0250 (15)0.0034 (15)−0.0327 (16)
C60.0649 (19)0.0628 (17)0.0726 (19)−0.0252 (15)0.0001 (16)−0.0303 (16)
C70.0700 (19)0.0682 (18)0.0774 (19)−0.0329 (16)0.0062 (17)−0.0322 (16)
C80.0739 (19)0.0740 (18)0.0771 (19)−0.0367 (17)0.0091 (16)−0.0352 (16)
C90.075 (2)0.0714 (19)0.089 (2)−0.0382 (17)0.0162 (18)−0.0419 (18)
C100.0551 (17)0.0641 (18)0.0634 (18)−0.0177 (15)0.0060 (15)−0.0289 (16)
C110.0466 (16)0.0540 (16)0.0557 (17)−0.0151 (14)0.0017 (14)−0.0264 (14)
C120.0492 (16)0.0474 (15)0.0514 (16)−0.0089 (13)0.0013 (14)−0.0256 (14)
C130.0568 (17)0.0577 (16)0.0588 (17)−0.0221 (14)0.0082 (14)−0.0292 (15)
C140.0582 (17)0.0511 (16)0.0594 (18)−0.0185 (14)0.0016 (15)−0.0251 (15)
C150.0669 (19)0.080 (2)0.0701 (19)−0.0280 (16)0.0146 (17)−0.0486 (17)
C160.0576 (18)0.0809 (19)0.0643 (18)−0.0245 (16)0.0168 (15)−0.0407 (17)
C170.103 (2)0.091 (2)0.095 (2)−0.059 (2)0.025 (2)−0.0444 (19)
C180.0515 (17)0.0588 (17)0.0602 (17)−0.0166 (14)0.0030 (15)−0.0268 (14)
C190.0462 (15)0.0476 (15)0.0546 (16)−0.0142 (13)0.0002 (14)−0.0208 (14)
C200.0490 (16)0.0572 (16)0.0580 (17)−0.0191 (14)0.0094 (15)−0.0201 (15)
C210.074 (2)0.0568 (17)0.0601 (17)−0.0202 (16)0.0069 (16)−0.0315 (15)
C220.0676 (19)0.0467 (16)0.0613 (18)−0.0192 (15)−0.0061 (16)−0.0192 (15)
C230.0651 (18)0.0658 (18)0.077 (2)−0.0300 (16)0.0125 (17)−0.0332 (17)
C240.0611 (18)0.0617 (17)0.0643 (17)−0.0230 (15)0.0104 (15)−0.0307 (15)
C250.161 (3)0.102 (2)0.091 (2)−0.063 (2)0.028 (2)−0.064 (2)
N1—C101.280 (3)C7—H7B0.9700
N1—O11.394 (2)C8—C91.501 (3)
N2—C181.266 (3)C8—H8A0.9700
N2—O21.409 (2)C8—H8B0.9700
O1—C11.443 (3)C9—H9A0.9700
O2—C91.410 (3)C9—H9B0.9700
O3—C121.353 (2)C10—C111.441 (3)
O3—H30.8200C10—H100.9300
O4—C141.366 (3)C11—C161.390 (3)
O4—C171.410 (3)C11—C121.390 (3)
O5—C201.349 (3)C12—C131.379 (3)
O5—H50.8200C13—C141.377 (3)
O6—C221.369 (3)C13—H130.9300
O6—C251.410 (3)C14—C151.377 (3)
C1—C21.476 (3)C15—C161.358 (3)
C1—H1A0.9700C15—H150.9300
C1—H1B0.9700C16—H160.9300
C2—C31.513 (3)C17—H17A0.9600
C2—H2A0.9700C17—H17B0.9600
C2—H2B0.9700C17—H17C0.9600
C3—C41.509 (3)C18—C191.446 (3)
C3—H3A0.9700C18—H180.9300
C3—H3B0.9700C19—C241.385 (3)
C4—C51.504 (3)C19—C201.394 (3)
C4—H4A0.9700C20—C211.384 (3)
C4—H4B0.9700C21—C221.367 (3)
C5—C61.512 (3)C21—H210.9300
C5—H5A0.9700C22—C231.383 (3)
C5—H5B0.9700C23—C241.366 (3)
C6—C71.511 (3)C23—H230.9300
C6—H6A0.9700C24—H240.9300
C6—H6B0.9700C25—H25A0.9600
C7—C81.512 (3)C25—H25B0.9600
C7—H7A0.9700C25—H25C0.9600
C10—N1—O1112.5 (2)C8—C9—H9A110.4
C18—N2—O2109.9 (2)O2—C9—H9B110.4
N1—O1—C1108.68 (18)C8—C9—H9B110.4
N2—O2—C9110.86 (18)H9A—C9—H9B108.6
C12—O3—H3109.5N1—C10—C11120.6 (2)
C14—O4—C17118.41 (19)N1—C10—H10119.7
C20—O5—H5109.5C11—C10—H10119.7
C22—O6—C25117.9 (2)C16—C11—C12117.1 (2)
O1—C1—C2106.5 (2)C16—C11—C10120.6 (2)
O1—C1—H1A110.4C12—C11—C10122.3 (2)
C2—C1—H1A110.4O3—C12—C13116.9 (2)
O1—C1—H1B110.4O3—C12—C11121.6 (2)
C2—C1—H1B110.4C13—C12—C11121.5 (2)
H1A—C1—H1B108.6C14—C13—C12119.3 (2)
C1—C2—C3115.4 (2)C14—C13—H13120.4
C1—C2—H2A108.4C12—C13—H13120.4
C3—C2—H2A108.4O4—C14—C15116.1 (2)
C1—C2—H2B108.4O4—C14—C13123.6 (2)
C3—C2—H2B108.4C15—C14—C13120.3 (2)
H2A—C2—H2B107.5C16—C15—C14119.7 (2)
C4—C3—C2111.8 (2)C16—C15—H15120.2
C4—C3—H3A109.3C14—C15—H15120.2
C2—C3—H3A109.3C15—C16—C11122.2 (2)
C4—C3—H3B109.3C15—C16—H16118.9
C2—C3—H3B109.3C11—C16—H16118.9
H3A—C3—H3B107.9O4—C17—H17A109.5
C5—C4—C3115.4 (2)O4—C17—H17B109.5
C5—C4—H4A108.4H17A—C17—H17B109.5
C3—C4—H4A108.4O4—C17—H17C109.5
C5—C4—H4B108.4H17A—C17—H17C109.5
C3—C4—H4B108.4H17B—C17—H17C109.5
H4A—C4—H4B107.5N2—C18—C19123.3 (2)
C4—C5—C6113.3 (2)N2—C18—H18118.3
C4—C5—H5A108.9C19—C18—H18118.3
C6—C5—H5A108.9C24—C19—C20117.4 (2)
C4—C5—H5B108.9C24—C19—C18119.8 (2)
C6—C5—H5B108.9C20—C19—C18122.8 (2)
H5A—C5—H5B107.7O5—C20—C21118.0 (2)
C7—C6—C5115.0 (2)O5—C20—C19121.3 (2)
C7—C6—H6A108.5C21—C20—C19120.8 (2)
C5—C6—H6A108.5C22—C21—C20119.7 (2)
C7—C6—H6B108.5C22—C21—H21120.1
C5—C6—H6B108.5C20—C21—H21120.1
H6A—C6—H6B107.5C21—C22—O6124.4 (3)
C6—C7—C8112.7 (2)C21—C22—C23120.8 (2)
C6—C7—H7A109.1O6—C22—C23114.8 (3)
C8—C7—H7A109.1C24—C23—C22118.7 (3)
C6—C7—H7B109.1C24—C23—H23120.7
C8—C7—H7B109.1C22—C23—H23120.7
H7A—C7—H7B107.8C23—C24—C19122.5 (2)
C9—C8—C7115.3 (2)C23—C24—H24118.7
C9—C8—H8A108.4C19—C24—H24118.7
C7—C8—H8A108.4O6—C25—H25A109.5
C9—C8—H8B108.4O6—C25—H25B109.5
C7—C8—H8B108.4H25A—C25—H25B109.5
H8A—C8—H8B107.5O6—C25—H25C109.5
O2—C9—C8106.6 (2)H25A—C25—H25C109.5
O2—C9—H9A110.4H25B—C25—H25C109.5
C10—N1—O1—C1178.4 (2)C12—C13—C14—C15−1.0 (4)
C18—N2—O2—C9175.3 (2)O4—C14—C15—C16−179.6 (2)
N1—O1—C1—C2176.5 (2)C13—C14—C15—C160.1 (4)
O1—C1—C2—C3−179.1 (2)C14—C15—C16—C110.3 (4)
C1—C2—C3—C4−178.0 (2)C12—C11—C16—C150.1 (4)
C2—C3—C4—C5178.9 (2)C10—C11—C16—C15179.3 (2)
C3—C4—C5—C6−176.9 (2)O2—N2—C18—C19178.71 (19)
C4—C5—C6—C7−178.7 (2)N2—C18—C19—C24−178.5 (2)
C5—C6—C7—C8−180.0 (2)N2—C18—C19—C202.1 (4)
C6—C7—C8—C9−178.3 (2)C24—C19—C20—O5−179.7 (2)
N2—O2—C9—C8−179.98 (18)C18—C19—C20—O5−0.2 (3)
C7—C8—C9—O2−177.8 (2)C24—C19—C20—C210.6 (3)
O1—N1—C10—C11179.65 (19)C18—C19—C20—C21−179.9 (2)
N1—C10—C11—C16−179.8 (2)O5—C20—C21—C22−179.9 (2)
N1—C10—C11—C12−0.7 (4)C19—C20—C21—C22−0.2 (4)
C16—C11—C12—O3178.9 (2)C20—C21—C22—O6179.2 (2)
C10—C11—C12—O3−0.3 (3)C20—C21—C22—C23−0.7 (4)
C16—C11—C12—C13−1.0 (3)C25—O6—C22—C215.4 (4)
C10—C11—C12—C13179.8 (2)C25—O6—C22—C23−174.7 (2)
O3—C12—C13—C14−178.4 (2)C21—C22—C23—C241.1 (4)
C11—C12—C13—C141.5 (3)O6—C22—C23—C24−178.8 (2)
C17—O4—C14—C15176.3 (2)C22—C23—C24—C19−0.6 (4)
C17—O4—C14—C13−3.4 (3)C20—C19—C24—C23−0.2 (3)
C12—C13—C14—O4178.7 (2)C18—C19—C24—C23−179.7 (2)
D—H···AD—HH···AD···AD—H···A
C17—H17B···O4i0.962.683.369 (3)129
C18—H18···O3ii0.932.403.295 (3)160
C25—H25C···O3iii0.962.593.541 (4)170
C25—H25B···O6iv0.962.613.469 (4)150
O3—H3···N10.821.862.583 (4)147
O5—H5···N20.821.942.663 (4)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C17—H17B⋯O4i0.962.683.369 (3)129
C18—H18⋯O3ii0.932.403.295 (3)160
C25—H25C⋯O3iii0.962.593.541 (4)170
C25—H25B⋯O6iv0.962.613.469 (4)150
O3—H3⋯N10.821.862.583 (4)147
O5—H5⋯N20.821.942.663 (4)147

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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