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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jun 21;64(Pt 7):o1323. doi: 10.1107/S1600536808017789

6,6′-Dimeth­oxy-2,2′-[(hexane-1,6-diyldi­oxy)bis­(nitrilo­methyl­idyne)]diphenol

Wen-Kui Dong a,*, Chun-Yu Zhao a, Jin-Kui Zhong a, Xiao-Lu Tang a, Tian-Zhi Yu b
PMCID: PMC2961880  PMID: 21202947

Abstract

In the title compound, C22H28N2O6, strong intra­molecular O—H⋯N hydrogen bonds and weak inter­molecular C—H⋯O hydrogen bonds stabilize the three-dimensional supra­molecular structure.

Related literature

For related literature, see: Akine et al. (2005 ▶); Costes et al. (2000 ▶); Dong et al. (2006 ▶, 2007 ▶); Duan et al. (2007 ▶); Hoshino (1998 ▶); Jacobsen et al. (1991 ▶); Katsuki (1995 ▶); Lacroix (2001 ▶); Srinivasan et al. (1986 ▶); Zhang et al. (1990 ▶).graphic file with name e-64-o1323-scheme1.jpg

Experimental

Crystal data

  • C22H28N2O6

  • M r = 416.46

  • Monoclinic, Inline graphic

  • a = 6.2913 (9) Å

  • b = 29.063 (3) Å

  • c = 12.0481 (15) Å

  • β = 100.063 (2)°

  • V = 2169.0 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 (2) K

  • 0.43 × 0.23 × 0.17 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.984

  • 10858 measured reflections

  • 3836 independent reflections

  • 2138 reflections with I > 2σ(I)

  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.047

  • wR(F 2) = 0.130

  • S = 1.08

  • 3836 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.14 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017789/hg2411sup1.cif

e-64-o1323-sup1.cif (22.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017789/hg2411Isup2.hkl

e-64-o1323-Isup2.hkl (188.1KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O5—H5⋯N2 0.82 1.95 2.662 (3) 145
O3—H3⋯N1 0.82 1.90 2.615 (3) 145
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Acknowledgments

This work was supported by the Foundation of the Education Department of Gansu Province (No. 0604-01) and the ‘Qing Lan’ Talent Engineering Funds of Lanzhou Jiaotong University (No. QL-03-01 A), which are gratefully acknowledged.

supplementary crystallographic information

Comment

Salen-type compound and its derivatives have attracted much attention to many organic as well as inorganic chemists, because these compounds can easily form complexes with various transition metal ions (Jacobsen et al.;1991, Katsuki et al.,1995). Some of them or their metal complexes are used as a catalyst in various organic reactions (Srinivasan et al., 1986; Zhang et al., 1990), nonlinear optical materials (Lacroix et al., 2001), and metallomesogens (Hoshino et al.,1998) or exhibit interesting magnetic properties (Costes et al., 2000) and so forth. To develop stable analogues of salen-type ligands, we synthesized a new class of salen-type bisoxime compounds on the basis of O-alkyl oxime moiety (–CH=N—O-(CH2)n-O—N=CH–) instead of the imine moiety (Dong et al., 2006; Duan et al., 2007). The larger electronegativity of oxygen atoms is expected to affect strongly the electronic properties of N2O2 coordination sphere, which can lead to different and novel properties and structures of the resulted complexes (Akine et al.,2005). Thus modification of a basic salen skeleton is very interesting and important. In this paper, a novel bisoxime ligand, 6,6'-dimethoxy-2,2'-[(hexane-1,6-diyldioxy)bis(nitrilomethylidyne)]diphenol (I) has been synthesized by 2 equiv. of 3-methoxysalicylidene and 1 equiv. of 1,6-bis(aminooxy)hexane, and shown in Fig. 1.

X-ray crystallographic analysis reveals the crystal structure of the bisoxime ligand (I), Which consists of discrete C22H28N2O6 molecules in which all bond lengths are in normal ranges. The dihedral angle of the two benzene rings is 20.9 (2)°. The oxime groups have anti-conformation, and there are strong O3—H3···N1 and O5—H5···N2 intramolecular hydrogen bonds and weak C7—H7···O3 and C22—H22A···C10 intermolecular hydrogen bonds, stabilize the three-dimensional supramolecuar structure of (I).

Experimental

The title compound (I) was synthesized according to an analogous method reported earlier (Dong et al., 2007). To an ethanol solution (5 ml) of 3-methoxysalicylidene (265.6 mg, 1.75 mmol) was added an ethanol (3 ml) solution of 1,6-bis(aminooxy)hexane (129.4 mg, 0.87 mmol). After the solution had been stirred at 328 K for 4 h, the mixture was filtered. The residue was washed successively with ethanol and ethanol/hexane (1:4), respectively. The product was dried under vacuum to yield 60.62 mg of (I). Yield, 16.7%. mp. 382–384 K. Anal. Calc. for C22H28N2O6: C, 63.45; H, 6.78; N, 6.73. Found: C, 63.47; H, 6.79; N, 6.61%.

Colorless prismatic single crystals suitable for X-ray diffraction studies were obtained after several weeks by slow evaporation from a mixture of ethanol/acetone (1:3) of (I) at room temperture.

Refinement

Non-H atoms were refined anisotropically. H atoms were treated as riding atoms with distances C—H = 0.96 (CH3), or C—H = 0.97 (CH2), or 0.93 Å (CH), O—H = 0.82 Å, and Uiso(H) = 1.2 Ueq(C) and 1.5 Ueq(O).

Figures

Fig. 1.

Fig. 1.

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The molecule structure of (I) with atom numbering. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

Crystal data

C22H28N2O6 F000 = 888
Mr = 416.46 Dx = 1.275 Mg m−3
Monoclinic, P21/n Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn Cell parameters from 2277 reflections
a = 6.2913 (9) Å θ = 2.2–22.7º
b = 29.063 (3) Å µ = 0.09 mm−1
c = 12.0481 (15) Å T = 298 (2) K
β = 100.063 (2)º Prismatic, colorless
V = 2169.0 (5) Å3 0.43 × 0.23 × 0.17 mm
Z = 4
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Data collection

Bruker SMART CCD area-detector diffractometer 3836 independent reflections
Radiation source: fine-focus sealed tube 2138 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.042
T = 298(2) K θmax = 25.0º
φ and ω scans θmin = 1.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996) h = −7→7
Tmin = 0.961, Tmax = 0.984 k = −34→34
10858 measured reflections l = −10→14
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Refinement

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)] = 0.047 H-atom parameters constrained
wR(F2) = 0.130   w = 1/[σ2(Fo2) + (0.054P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08 (Δ/σ)max < 0.001
3836 reflections Δρmax = 0.17 e Å−3
273 parameters Δρmin = −0.14 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Special details

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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
N1 1.1005 (3) 0.21438 (7) 0.56103 (16) 0.0423 (5)
N2 −0.1743 (4) −0.00593 (7) 0.76432 (19) 0.0534 (6)
O1 0.9073 (3) 0.19166 (6) 0.52040 (13) 0.0500 (5)
O2 0.0109 (3) 0.02112 (6) 0.78379 (15) 0.0651 (6)
O3 1.4536 (3) 0.23525 (5) 0.70115 (13) 0.0471 (5)
H3 1.3377 0.2222 0.6810 0.071*
O4 1.8128 (3) 0.27994 (6) 0.74024 (14) 0.0536 (5)
O5 −0.5254 (3) −0.04977 (6) 0.66091 (13) 0.0560 (5)
H5 −0.4150 −0.0344 0.6644 0.084*
O6 −0.8662 (3) −0.09771 (6) 0.67802 (14) 0.0583 (5)
C1 0.8437 (4) 0.16557 (8) 0.6096 (2) 0.0460 (7)
H1A 0.8146 0.1861 0.6686 0.055*
H1B 0.9593 0.1449 0.6416 0.055*
C2 0.6460 (4) 0.13858 (9) 0.5642 (2) 0.0498 (7)
H2A 0.6793 0.1166 0.5092 0.060*
H2B 0.5355 0.1592 0.5263 0.060*
C3 0.5602 (4) 0.11318 (9) 0.6573 (2) 0.0500 (7)
H3A 0.6754 0.0944 0.6983 0.060*
H3B 0.5203 0.1356 0.7096 0.060*
C4 0.3675 (4) 0.08263 (9) 0.6171 (2) 0.0563 (7)
H4A 0.2565 0.1004 0.5698 0.068*
H4B 0.4104 0.0578 0.5718 0.068*
C5 0.2762 (4) 0.06249 (9) 0.7145 (2) 0.0511 (7)
H5A 0.3877 0.0444 0.7606 0.061*
H5B 0.2386 0.0875 0.7607 0.061*
C6 0.0802 (4) 0.03258 (9) 0.6804 (2) 0.0535 (7)
H6A −0.0319 0.0491 0.6306 0.064*
H6B 0.1168 0.0051 0.6423 0.064*
C7 1.1556 (4) 0.24225 (8) 0.4897 (2) 0.0425 (6)
H7 1.0669 0.2460 0.4199 0.051*
C8 1.3543 (4) 0.26824 (7) 0.51555 (19) 0.0375 (6)
C9 1.4944 (4) 0.26352 (7) 0.61737 (19) 0.0364 (6)
C10 1.6878 (4) 0.28817 (8) 0.6385 (2) 0.0399 (6)
C11 1.7384 (4) 0.31800 (8) 0.5586 (2) 0.0508 (7)
H11 1.8668 0.3346 0.5722 0.061*
C12 1.5961 (5) 0.32325 (9) 0.4574 (2) 0.0577 (8)
H12 1.6297 0.3437 0.4036 0.069*
C13 1.4083 (5) 0.29895 (9) 0.4357 (2) 0.0520 (7)
H13 1.3153 0.3028 0.3674 0.062*
C14 2.0134 (4) 0.30314 (9) 0.7683 (2) 0.0622 (8)
H14A 2.0954 0.2989 0.7090 0.093*
H14B 2.0923 0.2908 0.8374 0.093*
H14C 1.9881 0.3354 0.7777 0.093*
C15 −0.2267 (4) −0.01909 (8) 0.8565 (2) 0.0526 (7)
H15 −0.1392 −0.0103 0.9235 0.063*
C16 −0.4139 (4) −0.04678 (8) 0.8628 (2) 0.0457 (7)
C17 −0.5556 (4) −0.06051 (8) 0.7667 (2) 0.0410 (6)
C18 −0.7374 (4) −0.08642 (8) 0.7769 (2) 0.0434 (6)
C19 −0.7739 (4) −0.09855 (9) 0.8825 (2) 0.0518 (7)
H19 −0.8947 −0.1160 0.8894 0.062*
C20 −0.6334 (5) −0.08513 (9) 0.9779 (2) 0.0602 (8)
H20 −0.6594 −0.0936 1.0488 0.072*
C21 −0.4562 (5) −0.05942 (9) 0.9683 (2) 0.0570 (8)
H21 −0.3625 −0.0502 1.0329 0.068*
C22 −1.0452 (4) −0.12698 (9) 0.6835 (2) 0.0630 (8)
H22A −0.9947 −0.1555 0.7185 0.094*
H22B −1.1217 −0.1328 0.6086 0.094*
H22C −1.1402 −0.1123 0.7269 0.094*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N1 0.0391 (13) 0.0454 (12) 0.0418 (12) −0.0095 (10) 0.0050 (10) −0.0060 (10)
N2 0.0475 (15) 0.0481 (13) 0.0663 (16) −0.0098 (11) 0.0147 (12) 0.0014 (12)
O1 0.0465 (12) 0.0622 (11) 0.0398 (10) −0.0191 (9) 0.0033 (8) 0.0022 (8)
O2 0.0556 (13) 0.0741 (13) 0.0667 (13) −0.0256 (11) 0.0141 (10) 0.0043 (10)
O3 0.0448 (11) 0.0539 (10) 0.0411 (10) −0.0083 (8) 0.0035 (8) 0.0085 (8)
O4 0.0394 (11) 0.0614 (11) 0.0544 (12) −0.0089 (9) −0.0073 (9) 0.0026 (9)
O5 0.0593 (13) 0.0662 (12) 0.0453 (11) −0.0128 (10) 0.0167 (9) 0.0018 (9)
O6 0.0565 (13) 0.0676 (12) 0.0500 (12) −0.0168 (10) 0.0070 (10) 0.0007 (9)
C1 0.0467 (17) 0.0468 (15) 0.0452 (16) −0.0046 (13) 0.0100 (13) 0.0060 (13)
C2 0.0493 (17) 0.0531 (16) 0.0477 (16) −0.0098 (14) 0.0100 (13) 0.0033 (13)
C3 0.0519 (18) 0.0507 (16) 0.0486 (16) −0.0027 (14) 0.0124 (14) 0.0034 (13)
C4 0.0592 (19) 0.0590 (17) 0.0524 (17) −0.0115 (15) 0.0144 (15) 0.0052 (14)
C5 0.0487 (18) 0.0516 (16) 0.0542 (17) −0.0047 (14) 0.0122 (14) 0.0043 (13)
C6 0.0513 (18) 0.0515 (16) 0.0592 (18) −0.0044 (14) 0.0136 (14) 0.0080 (14)
C7 0.0453 (17) 0.0452 (15) 0.0354 (14) −0.0035 (13) 0.0023 (12) −0.0006 (12)
C8 0.0431 (16) 0.0349 (13) 0.0346 (14) −0.0037 (12) 0.0073 (12) −0.0024 (11)
C9 0.0390 (16) 0.0345 (13) 0.0360 (14) 0.0005 (12) 0.0074 (12) −0.0011 (11)
C10 0.0390 (16) 0.0387 (14) 0.0420 (15) −0.0009 (12) 0.0067 (13) −0.0046 (12)
C11 0.0482 (18) 0.0486 (16) 0.0565 (18) −0.0137 (14) 0.0115 (15) −0.0038 (14)
C12 0.071 (2) 0.0547 (17) 0.0498 (18) −0.0166 (16) 0.0174 (16) 0.0079 (14)
C13 0.063 (2) 0.0549 (16) 0.0367 (15) −0.0101 (15) 0.0058 (14) 0.0053 (13)
C14 0.0425 (18) 0.0679 (19) 0.072 (2) −0.0089 (15) −0.0016 (15) −0.0131 (15)
C15 0.0488 (18) 0.0548 (17) 0.0531 (18) −0.0098 (14) 0.0054 (14) 0.0035 (14)
C16 0.0481 (18) 0.0412 (15) 0.0489 (17) −0.0027 (13) 0.0119 (14) 0.0012 (13)
C17 0.0466 (17) 0.0378 (14) 0.0417 (16) 0.0034 (13) 0.0164 (13) 0.0030 (12)
C18 0.0436 (17) 0.0427 (15) 0.0438 (16) −0.0018 (13) 0.0073 (13) −0.0020 (12)
C19 0.0516 (18) 0.0535 (16) 0.0526 (18) −0.0097 (14) 0.0151 (15) 0.0024 (14)
C20 0.070 (2) 0.0666 (19) 0.0471 (18) −0.0112 (17) 0.0197 (16) 0.0049 (15)
C21 0.064 (2) 0.0618 (18) 0.0434 (17) −0.0077 (16) 0.0058 (15) 0.0012 (14)
C22 0.0527 (19) 0.0665 (18) 0.069 (2) −0.0166 (16) 0.0082 (15) −0.0045 (15)
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Geometric parameters (Å, °)

N1—C7 1.273 (3) C6—H6B 0.9700
N1—O1 1.395 (2) C7—C8 1.447 (3)
N2—C15 1.271 (3) C7—H7 0.9300
N2—O2 1.391 (3) C8—C9 1.387 (3)
O1—C1 1.428 (3) C8—C13 1.397 (3)
O2—C6 1.429 (3) C9—C10 1.397 (3)
O3—C9 1.360 (3) C10—C11 1.373 (3)
O3—H3 0.8200 C11—C12 1.390 (3)
O4—C10 1.357 (3) C11—H11 0.9300
O4—C14 1.418 (3) C12—C13 1.362 (3)
O5—C17 1.357 (3) C12—H12 0.9300
O5—H5 0.8200 C13—H13 0.9300
O6—C18 1.359 (3) C14—H14A 0.9600
O6—C22 1.422 (3) C14—H14B 0.9600
C1—C2 1.491 (3) C14—H14C 0.9600
C1—H1A 0.9700 C15—C16 1.439 (3)
C1—H1B 0.9700 C15—H15 0.9300
C2—C3 1.518 (3) C16—C17 1.391 (3)
C2—H2A 0.9700 C16—C21 1.392 (3)
C2—H2B 0.9700 C17—C18 1.393 (3)
C3—C4 1.512 (3) C18—C19 1.377 (3)
C3—H3A 0.9700 C19—C20 1.379 (4)
C3—H3B 0.9700 C19—H19 0.9300
C4—C5 1.511 (3) C20—C21 1.364 (3)
C4—H4A 0.9700 C20—H20 0.9300
C4—H4B 0.9700 C21—H21 0.9300
C5—C6 1.506 (3) C22—H22A 0.9600
C5—H5A 0.9700 C22—H22B 0.9600
C5—H5B 0.9700 C22—H22C 0.9600
C6—H6A 0.9700
C7—N1—O1 112.83 (19) C13—C8—C7 119.3 (2)
C15—N2—O2 111.1 (2) O3—C9—C8 122.9 (2)
N1—O1—C1 109.19 (17) O3—C9—C10 116.5 (2)
N2—O2—C6 111.04 (19) C8—C9—C10 120.6 (2)
C9—O3—H3 109.5 O4—C10—C11 125.1 (2)
C10—O4—C14 118.9 (2) O4—C10—C9 115.0 (2)
C17—O5—H5 109.5 C11—C10—C9 119.8 (2)
C18—O6—C22 117.4 (2) C10—C11—C12 119.5 (2)
O1—C1—C2 109.2 (2) C10—C11—H11 120.3
O1—C1—H1A 109.8 C12—C11—H11 120.3
C2—C1—H1A 109.8 C13—C12—C11 121.0 (2)
O1—C1—H1B 109.8 C13—C12—H12 119.5
C2—C1—H1B 109.8 C11—C12—H12 119.5
H1A—C1—H1B 108.3 C12—C13—C8 120.4 (2)
C1—C2—C3 111.5 (2) C12—C13—H13 119.8
C1—C2—H2A 109.3 C8—C13—H13 119.8
C3—C2—H2A 109.3 O4—C14—H14A 109.5
C1—C2—H2B 109.3 O4—C14—H14B 109.5
C3—C2—H2B 109.3 H14A—C14—H14B 109.5
H2A—C2—H2B 108.0 O4—C14—H14C 109.5
C4—C3—C2 114.7 (2) H14A—C14—H14C 109.5
C4—C3—H3A 108.6 H14B—C14—H14C 109.5
C2—C3—H3A 108.6 N2—C15—C16 123.7 (3)
C4—C3—H3B 108.6 N2—C15—H15 118.2
C2—C3—H3B 108.6 C16—C15—H15 118.2
H3A—C3—H3B 107.6 C17—C16—C21 119.2 (2)
C5—C4—C3 111.8 (2) C17—C16—C15 121.8 (2)
C5—C4—H4A 109.3 C21—C16—C15 119.0 (2)
C3—C4—H4A 109.3 O5—C17—C16 122.8 (2)
C5—C4—H4B 109.3 O5—C17—C18 117.4 (2)
C3—C4—H4B 109.3 C16—C17—C18 119.9 (2)
H4A—C4—H4B 107.9 O6—C18—C19 125.3 (2)
C6—C5—C4 114.6 (2) O6—C18—C17 115.2 (2)
C6—C5—H5A 108.6 C19—C18—C17 119.5 (2)
C4—C5—H5A 108.6 C18—C19—C20 120.8 (3)
C6—C5—H5B 108.6 C18—C19—H19 119.6
C4—C5—H5B 108.6 C20—C19—H19 119.6
H5A—C5—H5B 107.6 C21—C20—C19 119.9 (3)
O2—C6—C5 104.9 (2) C21—C20—H20 120.1
O2—C6—H6A 110.8 C19—C20—H20 120.1
C5—C6—H6A 110.8 C20—C21—C16 120.8 (3)
O2—C6—H6B 110.8 C20—C21—H21 119.6
C5—C6—H6B 110.8 C16—C21—H21 119.6
H6A—C6—H6B 108.8 O6—C22—H22A 109.5
N1—C7—C8 120.9 (2) O6—C22—H22B 109.5
N1—C7—H7 119.5 H22A—C22—H22B 109.5
C8—C7—H7 119.5 O6—C22—H22C 109.5
C9—C8—C13 118.6 (2) H22A—C22—H22C 109.5
C9—C8—C7 122.0 (2) H22B—C22—H22C 109.5
C7—N1—O1—C1 −172.91 (19) C10—C11—C12—C13 −0.6 (4)
C15—N2—O2—C6 175.0 (2) C11—C12—C13—C8 0.3 (4)
N1—O1—C1—C2 −175.89 (18) C9—C8—C13—C12 0.8 (4)
O1—C1—C2—C3 −175.30 (19) C7—C8—C13—C12 −178.9 (2)
C1—C2—C3—C4 −176.4 (2) O2—N2—C15—C16 178.7 (2)
C2—C3—C4—C5 −173.9 (2) N2—C15—C16—C17 −1.4 (4)
C3—C4—C5—C6 178.6 (2) N2—C15—C16—C21 179.8 (3)
N2—O2—C6—C5 178.64 (19) C21—C16—C17—O5 −179.7 (2)
C4—C5—C6—O2 −174.7 (2) C15—C16—C17—O5 1.5 (4)
O1—N1—C7—C8 −178.54 (19) C21—C16—C17—C18 0.3 (4)
N1—C7—C8—C9 1.1 (4) C15—C16—C17—C18 −178.5 (2)
N1—C7—C8—C13 −179.2 (2) C22—O6—C18—C19 −4.5 (4)
C13—C8—C9—O3 178.6 (2) C22—O6—C18—C17 175.5 (2)
C7—C8—C9—O3 −1.7 (4) O5—C17—C18—O6 −0.6 (3)
C13—C8—C9—C10 −1.5 (3) C16—C17—C18—O6 179.5 (2)
C7—C8—C9—C10 178.2 (2) O5—C17—C18—C19 179.4 (2)
C14—O4—C10—C11 −0.6 (3) C16—C17—C18—C19 −0.6 (4)
C14—O4—C10—C9 179.4 (2) O6—C18—C19—C20 −179.7 (2)
O3—C9—C10—O4 1.1 (3) C17—C18—C19—C20 0.4 (4)
C8—C9—C10—O4 −178.8 (2) C18—C19—C20—C21 0.2 (4)
O3—C9—C10—C11 −178.9 (2) C19—C20—C21—C16 −0.5 (4)
C8—C9—C10—C11 1.2 (3) C17—C16—C21—C20 0.3 (4)
O4—C10—C11—C12 179.9 (2) C15—C16—C21—C20 179.1 (2)
C9—C10—C11—C12 −0.1 (4)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O5—H5···N2 0.82 1.95 2.662 (3) 145
O3—H3···N1 0.82 1.90 2.615 (3) 145
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2411).

References

  1. Akine, S., Takanori, T., Dong, W. K. & Nabeshima, T. (2005). J. Org. Chem.70, 1704–1711. [DOI] [PubMed]
  2. Costes, J. P., Dahan, F. & Dupuis, A. (2000). Inorg. Chem.39, 165–168. [DOI] [PubMed]
  3. Dong, W.-K., Feng, J. H. & Yang, X. Q. (2006). Z. Kristallogr. New Cryst. Struct.221, 447–448.
  4. Dong, W. K., He, X. N., Dong, C. M., Wang, L., Zhong, J. K., Chen, X. & Yu, T. Z. (2007). Z. Kristallogr. New Cryst. Struct.222, 289–290.
  5. Duan, J.-G., Dong, C.-M., Shi, J.-Y., Wu, L. & Dong, W.-K. (2007). Acta Cryst. E63, o2704–o2705.
  6. Hoshino, N. (1998). Coord. Chem. Rev.174, 77–108.
  7. Jacobsen, E. N., Zhang, W., Muci, A. R., Ecker, J. R. & Deng, L. (1991). J. Am. Chem. Soc.113, 7063–7064.
  8. Katsuki, T. (1995). Coord. Chem. Rev.140, 189–214.
  9. Lacroix, P. G. (2001). Eur. J. Inorg. Chem.2, 339–348.
  10. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  13. Srinivasan, K., Michaud, P. & Kochi, J. K. (1986). J. Am. Chem. Soc.108, 2309–2320. [DOI] [PubMed]
  14. Zhang, W., Loebach, J. L., Wilson, S. R. & Jacobsen, E. N. (1990). J. Am. Chem. Soc.112, 2801–2803.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808017789/hg2411sup1.cif

e-64-o1323-sup1.cif (22.3KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017789/hg2411Isup2.hkl

e-64-o1323-Isup2.hkl (188.1KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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