Literature DB >> 21578323

(1R,2R)-1,2-Diphenyl-1,2-bis-(1H-tetra-zol-1-yl)ethane.

Franz Werner, Kurt Mereiter, Kenji Tokuno, Yuki Inagaki, Miki Hasegawa.   

Abstract

The title compound, C(16)H(14)N(8), is a new chiral ligand designed for applications in supra-molecular chemistry and Fe(2+) spin-crossover complexes. The crystal structure shows a herring-bone arrangement of the mol-ecules, which are mutually linked via inter-molecular C-H⋯N inter-actions mainly donated by the alkyl and tetra-zole H atoms.

Entities:  

Year:  2009        PMID： 21578323      PMCID： PMC2970974          DOI： 10.1107/S160053680904094X

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


Related literature

For the general synthetic procedure, see: Kamiya & Saito (1973 ▶). For the crystal structure of the chiral starting material, see: Jones et al. (2003 ▶). For studies on the crystal structures and packing of di-tetra­zolylalkanes, see: Grunert et al. (2005 ▶); Absmeier et al. (2006 ▶). For supra­molecular compounds made up of di-tetra­zolylalkanes, see: Liu et al. (2008 ▶, 2009 ▶); Yu et al. (2008 ▶). For Fe2+ spin-crossover complexes based on di-tetra­zolylalkanes, see: Grunert et al. (2004 ▶); Quesada et al. (2007 ▶); Bialonska et al. (2008 ▶). The absolute structure of the title compound could not be determined from the diffraction data but was known from the chiral precursor compound (1R,2R)-(+)-1,2-diphenyl-1,2-ethanediamine, see: Jones et al. (2003 ▶).

Experimental

Crystal data

C16H14N8 M = 318.35 Orthorhombic, a = 8.3088 (4) Å b = 11.2802 (6) Å c = 16.5187 (9) Å V = 1548.21 (14) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.65 × 0.55 × 0.46 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.86, T max = 0.96 17102 measured reflections 2551 independent reflections 2475 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.092 S = 1.10 2551 reflections 217 parameters H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.30 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S160053680904094X/su2147sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S160053680904094X/su2147Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C16H14N8F(000) = 664
Mr = 318.35Dx = 1.366 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 6154 reflections
a = 8.3088 (4) Åθ = 2.5–30.0°
b = 11.2802 (6) ŵ = 0.09 mm−1
c = 16.5187 (9) ÅT = 100 K
V = 1548.21 (14) Å3Prism, colourless
Z = 40.65 × 0.55 × 0.46 mm
Bruker SMART APEX CCD diffractometer2551 independent reflections
Radiation source: fine-focus sealed tube2475 reflections with I > 2σ(I)
graphiteRint = 0.018
ω and φ scansθmax = 30.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −11→11
Tmin = 0.86, Tmax = 0.96k = −15→14
17102 measured reflectionsl = −23→23
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H-atom parameters constrained
wR(F2) = 0.092w = 1/[σ2(Fo2) + (0.0636P)2 + 0.1943P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
2551 reflectionsΔρmax = 0.33 e Å−3
217 parametersΔρmin = −0.30 e Å−3
0 restraintsAbsolute structure: known from the chirality of the precursor used; Friedel pairs merged
Primary atom site location: structure-invariant direct methods
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
N10.98462 (13)0.55207 (9)0.07313 (6)0.01376 (19)
N21.00108 (15)0.64765 (10)0.02443 (7)0.0189 (2)
N31.14022 (15)0.63675 (11)−0.01065 (7)0.0210 (2)
N41.21530 (15)0.53546 (11)0.01269 (7)0.0220 (2)
N50.85774 (13)0.73023 (9)0.18013 (6)0.0135 (2)
N60.90650 (14)0.71246 (10)0.25717 (6)0.0176 (2)
N70.99083 (15)0.80496 (10)0.27687 (7)0.0192 (2)
N80.99906 (15)0.88385 (10)0.21407 (7)0.0200 (2)
C11.11653 (16)0.48451 (12)0.06448 (8)0.0189 (2)
H11.13560.41150.09150.023*
C20.83462 (14)0.52879 (10)0.11786 (7)0.0125 (2)
H20.86130.48690.16950.015*
C30.74954 (14)0.64654 (10)0.13802 (7)0.0123 (2)
H30.71710.68400.08560.015*
C40.91482 (17)0.83523 (11)0.15502 (8)0.0173 (2)
H40.89740.86910.10310.021*
C50.72240 (15)0.45132 (11)0.06816 (7)0.0141 (2)
C60.69622 (17)0.47520 (12)−0.01377 (7)0.0175 (2)
H60.75310.5380−0.03930.021*
C70.58752 (18)0.40772 (13)−0.05813 (8)0.0214 (3)
H70.57140.4236−0.11400.026*
C80.50251 (19)0.31696 (12)−0.02063 (9)0.0237 (3)
H80.42700.2715−0.05070.028*
C90.52807 (18)0.29277 (12)0.06099 (9)0.0239 (3)
H90.46990.23080.08670.029*
C100.63881 (17)0.35930 (11)0.10515 (8)0.0193 (2)
H100.65720.34170.16060.023*
C110.59769 (15)0.62608 (11)0.18692 (7)0.0144 (2)
C120.45409 (17)0.67425 (12)0.15886 (8)0.0188 (3)
H120.45290.71890.11010.023*
C130.31198 (17)0.65725 (13)0.20212 (9)0.0240 (3)
H130.21440.69090.18300.029*
C140.31241 (18)0.59140 (14)0.27300 (9)0.0257 (3)
H140.21550.58040.30260.031*
C150.45537 (19)0.54143 (13)0.30064 (9)0.0249 (3)
H150.45550.49530.34870.030*
C160.59844 (17)0.55868 (12)0.25815 (8)0.0198 (3)
H160.69590.52490.27740.024*
U11U22U33U12U13U23
N10.0135 (4)0.0139 (4)0.0139 (4)−0.0001 (4)0.0009 (4)0.0007 (3)
N20.0194 (5)0.0180 (5)0.0192 (5)−0.0002 (4)0.0040 (4)0.0050 (4)
N30.0196 (5)0.0222 (5)0.0214 (5)−0.0008 (4)0.0051 (4)0.0015 (4)
N40.0176 (5)0.0245 (6)0.0238 (5)0.0014 (4)0.0047 (4)0.0003 (4)
N50.0126 (4)0.0143 (4)0.0134 (4)−0.0007 (4)−0.0011 (4)−0.0005 (3)
N60.0184 (5)0.0212 (5)0.0132 (4)−0.0027 (4)−0.0027 (4)−0.0006 (4)
N70.0191 (5)0.0201 (5)0.0186 (4)−0.0014 (4)−0.0019 (4)−0.0035 (4)
N80.0196 (5)0.0168 (5)0.0235 (5)−0.0016 (4)−0.0041 (4)−0.0014 (4)
C10.0155 (5)0.0192 (6)0.0219 (6)0.0029 (5)0.0017 (5)0.0008 (5)
C20.0111 (5)0.0139 (5)0.0124 (4)−0.0007 (4)0.0011 (4)0.0006 (4)
C30.0110 (5)0.0135 (5)0.0124 (4)−0.0006 (4)−0.0006 (4)−0.0006 (4)
C40.0172 (6)0.0143 (5)0.0204 (5)−0.0016 (4)−0.0030 (4)0.0013 (4)
C50.0129 (5)0.0135 (5)0.0157 (5)−0.0004 (4)−0.0002 (4)−0.0017 (4)
C60.0183 (6)0.0188 (5)0.0155 (5)−0.0001 (5)0.0003 (4)−0.0011 (4)
C70.0228 (6)0.0226 (6)0.0189 (5)0.0018 (5)−0.0037 (5)−0.0057 (5)
C80.0221 (6)0.0177 (6)0.0314 (7)0.0001 (5)−0.0072 (6)−0.0067 (5)
C90.0233 (6)0.0169 (6)0.0315 (7)−0.0056 (5)−0.0027 (5)0.0007 (5)
C100.0206 (6)0.0160 (5)0.0213 (5)−0.0029 (5)−0.0018 (5)0.0019 (5)
C110.0130 (5)0.0152 (5)0.0151 (5)−0.0016 (4)0.0019 (4)−0.0031 (4)
C120.0146 (6)0.0195 (6)0.0223 (6)−0.0002 (4)0.0003 (4)−0.0018 (5)
C130.0133 (6)0.0265 (7)0.0324 (7)−0.0001 (5)0.0035 (5)−0.0054 (6)
C140.0197 (6)0.0262 (7)0.0310 (7)−0.0059 (5)0.0106 (5)−0.0075 (6)
C150.0264 (7)0.0262 (7)0.0222 (6)−0.0056 (5)0.0090 (5)0.0002 (5)
C160.0190 (6)0.0222 (6)0.0183 (5)−0.0013 (5)0.0025 (5)0.0006 (5)
N1—C11.3425 (16)C6—C71.3900 (18)
N1—N21.3521 (14)C6—H60.9500
N1—C21.4725 (15)C7—C81.389 (2)
N2—N31.2991 (16)C7—H70.9500
N3—N41.3577 (17)C8—C91.392 (2)
N4—C11.3176 (17)C8—H80.9500
N5—C41.3416 (16)C9—C101.3935 (18)
N5—N61.3504 (14)C9—H90.9500
N5—C31.4777 (15)C10—H100.9500
N6—N71.2984 (16)C11—C121.3906 (18)
N7—N81.3685 (15)C11—C161.4008 (17)
N8—C41.3199 (17)C12—C131.3934 (19)
C1—H10.9500C12—H120.9500
C2—C51.5188 (16)C13—C141.387 (2)
C2—C31.5410 (16)C13—H130.9500
C2—H21.0000C14—C151.392 (2)
C3—C111.5158 (17)C14—H140.9500
C3—H31.0000C15—C161.3941 (19)
C4—H40.9500C15—H150.9500
C5—C101.3903 (17)C16—H160.9500
C5—C61.3971 (16)
C1—N1—N2107.87 (11)C7—C6—C5120.41 (12)
C1—N1—C2130.02 (10)C7—C6—H6119.8
N2—N1—C2121.76 (10)C5—C6—H6119.8
N3—N2—N1106.26 (11)C8—C7—C6119.93 (12)
N2—N3—N4111.21 (11)C8—C7—H7120.0
C1—N4—N3105.39 (11)C6—C7—H7120.0
C4—N5—N6108.45 (10)C7—C8—C9119.91 (13)
C4—N5—C3129.31 (10)C7—C8—H8120.0
N6—N5—C3122.09 (10)C9—C8—H8120.0
N7—N6—N5106.19 (10)C8—C9—C10120.14 (13)
N6—N7—N8111.07 (10)C8—C9—H9119.9
C4—N8—N7105.28 (10)C10—C9—H9119.9
N4—C1—N1109.26 (11)C5—C10—C9120.13 (12)
N4—C1—H1125.4C5—C10—H10119.9
N1—C1—H1125.4C9—C10—H10119.9
N1—C2—C5110.55 (9)C12—C11—C16119.73 (12)
N1—C2—C3110.06 (9)C12—C11—C3118.49 (11)
C5—C2—C3109.34 (9)C16—C11—C3121.77 (11)
N1—C2—H2109.0C11—C12—C13120.15 (13)
C5—C2—H2109.0C11—C12—H12119.9
C3—C2—H2109.0C13—C12—H12119.9
N5—C3—C11110.66 (9)C14—C13—C12120.31 (13)
N5—C3—C2111.92 (9)C14—C13—H13119.8
C11—C3—C2111.46 (10)C12—C13—H13119.8
N5—C3—H3107.5C13—C14—C15119.75 (12)
C11—C3—H3107.5C13—C14—H14120.1
C2—C3—H3107.5C15—C14—H14120.1
N8—C4—N5109.01 (11)C14—C15—C16120.40 (13)
N8—C4—H4125.5C14—C15—H15119.8
N5—C4—H4125.5C16—C15—H15119.8
C10—C5—C6119.47 (12)C15—C16—C11119.65 (13)
C10—C5—C2119.92 (10)C15—C16—H16120.2
C6—C5—C2120.55 (11)C11—C16—H16120.2
C1—N1—N2—N3−0.94 (14)C3—N5—C4—N8175.92 (12)
C2—N1—N2—N3−174.78 (10)N1—C2—C5—C10137.82 (11)
N1—N2—N3—N40.90 (14)C3—C2—C5—C10−100.87 (13)
N2—N3—N4—C1−0.50 (15)N1—C2—C5—C6−45.31 (15)
C4—N5—N6—N7−0.14 (14)C3—C2—C5—C676.01 (13)
C3—N5—N6—N7−176.11 (11)C10—C5—C6—C70.03 (19)
N5—N6—N7—N8−0.09 (14)C2—C5—C6—C7−176.86 (12)
N6—N7—N8—C40.30 (14)C5—C6—C7—C80.9 (2)
N3—N4—C1—N1−0.11 (15)C6—C7—C8—C9−0.9 (2)
N2—N1—C1—N40.66 (15)C7—C8—C9—C10−0.1 (2)
C2—N1—C1—N4173.81 (12)C6—C5—C10—C9−0.98 (19)
C1—N1—C2—C5−81.28 (15)C2—C5—C10—C9175.93 (12)
N2—N1—C2—C591.05 (13)C8—C9—C10—C51.0 (2)
C1—N1—C2—C3157.83 (12)N5—C3—C11—C12108.50 (12)
N2—N1—C2—C3−29.83 (14)C2—C3—C11—C12−126.26 (12)
C4—N5—C3—C11−120.73 (14)N5—C3—C11—C16−72.66 (14)
N6—N5—C3—C1154.32 (14)C2—C3—C11—C1652.57 (15)
C4—N5—C3—C2114.30 (13)C16—C11—C12—C131.08 (19)
N6—N5—C3—C2−70.65 (13)C3—C11—C12—C13179.94 (12)
N1—C2—C3—N5−53.30 (12)C11—C12—C13—C14−0.6 (2)
C5—C2—C3—N5−174.92 (9)C12—C13—C14—C15−0.5 (2)
N1—C2—C3—C11−177.83 (9)C13—C14—C15—C161.0 (2)
C5—C2—C3—C1160.56 (12)C14—C15—C16—C11−0.4 (2)
N7—N8—C4—N5−0.38 (15)C12—C11—C16—C15−0.58 (19)
N6—N5—C4—N80.34 (15)C3—C11—C16—C15−179.40 (12)
D—H···AD—HH···AD···AD—H···A
C1—H1···N7i0.952.703.430 (2)134
C2—H2···N7i1.002.553.392 (2)142
C2—H2···N8i1.002.533.506 (2)165
C3—H3···N3ii1.002.463.351 (2)149
C4—H4···N3ii0.952.633.315 (2)130
C4—H4···N4ii0.952.673.543 (2)154
C6—H6···N20.952.623.256 (2)124
C7—H7···N6iii0.952.633.339 (2)132
C12—H12···N2ii0.952.713.655 (2)171
C13—H13···N7iv0.952.743.379 (2)125
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C1—H1⋯N7i0.952.703.430 (2)134
C2—H2⋯N7i1.002.553.392 (2)142
C2—H2⋯N8i1.002.533.506 (2)165
C3—H3⋯N3ii1.002.463.351 (2)149
C4—H4⋯N3ii0.952.633.315 (2)130
C4—H4⋯N4ii0.952.673.543 (2)154
C6—H6⋯N20.952.623.256 (2)124
C7—H7⋯N6iii0.952.633.339 (2)132
C12—H12⋯N2ii0.952.713.655 (2)171
C13—H13⋯N7iv0.952.743.379 (2)125

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

  5 in total

1.  Both spacer length and parity influence the thermal and light-induced properties of iron(II) alpha,omega-bis(tetrazole-1-yl)alkane coordination polymers.

Authors:  Alina Absmeier; Matthias Bartel; Chiara Carbonera; Guy N L Jameson; Peter Weinberger; Andrea Caneschi; Kurt Mereiter; Jean-François Létard; Wolfgang Linert
Journal:  Chemistry       Date:  2006-03-01       Impact factor: 5.236

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  [Fe(mu-btzmp)2(btzmp)2](ClO4)2: a doubly-bridged 1D spin-transition bistetrazole-based polymer showing thermal hysteresis behaviour.

Authors:  Manuel Quesada; Huub Kooijman; Patrick Gamez; José Sánchez Costa; Petra J van Koningsbruggen; Peter Weinberger; Michael Reissner; Anthony L Spek; Jaap G Haasnoot; Jan Reedijk
Journal:  Dalton Trans       Date:  2007-10-04       Impact factor: 4.390

4.  A new family of spin-crossover complexes based on a FeII(tetrazolyl)4(MeCN)2-type core.

Authors:  Agata Białońska; Robert Bronisz; Marek Weselski
Journal:  Inorg Chem       Date:  2008-04-29       Impact factor: 5.165

5.  Structure and physical properties of [micro-tris(1,4-bis(tetrazol-1-yl)butane-N4,N4')iron(II)] bis(hexafluorophosphate), a new Fe(II) spin-crossover compound with a three-dimensional threefold interlocked crystal lattice.

Authors:  C Matthias Grunert; Johannes Schweifer; Peter Weinberger; Wolfgang Linert; Kurt Mereiter; Gerfried Hilscher; Martin Müller; Günter Wiesinger; Petra J van Koningsbruggen
Journal:  Inorg Chem       Date:  2004-01-12       Impact factor: 5.165
  5 in total
  2 in total

1.  Poly[[bis-{μ(3)-tris-[2-(1H-tetra-zol-1-yl)eth-yl]amine}copper(II)] bis-(perchlorate)].

Authors:  Franz Werner; Kenji Tokuno; Miki Hasegawa; Wolfgang Linert; Kurt Mereiter
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-03-13

2.  1-(2,2-Diphenyl-eth-yl)-1H-tetra-zole.

Authors:  Myrvete Tafili-Kryeziu; Kurt Mereiter; Wolfgang Linert; Franz Werner
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-27
  2 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.