Literature DB >> 21580502

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

Franz Werner, Kenji Tokuno, Miki Hasegawa, Wolfgang Linert, Kurt Mereiter.   

Abstract

In the title compound, {[Cu(C(9)H(15)N(13))(2)](ClO(4))(2)}(n), the Cu(2+) cation lies on an inversion center and is coordinated by the tetra-zole N(4) atoms of six symmetry-equivalent tris-[2-(1H-tetra-zol-1-yl)eth-yl]amine ligands (t(3)z) in the form of a Jahn-Teller-distorted octa-hedron with Cu-N bond distances of 2.0210 (8), 2.0259 (8) and 2.4098 (8) Å. The tertiary amine N atom is stereochemically inactive. The cationic part of the structure, viz. [Cu(t(3)z)(2)](2+), forms an infinite two-dimensional network parallel to (100), in pockets of which the perchlorate anions reside. The individual networks are partially inter-locked and held together by C-H⋯O inter-actions to the perchlorate anions and C-H⋯N inter-actions to tetra-zole N atoms.

Entities:  

Year:  2010        PMID： 21580502      PMCID： PMC2983878          DOI： 10.1107/S1600536810008998

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


Related literature

For a general procedure for the synthesis of tetra­zoles, see: Kamiya & Saito (1973 ▶). For the crystal structures of the t 3 z ligand and its complex with Cu(NO3)2, see: Hartdegen et al. (2009 ▶). For supra­molecular compounds made up of di-tetra­zolylalkanes, see: Liu et al. (2008 ▶); Yu et al. (2008 ▶). For Fe2+ spin-crossover complexes based on di-tetra­zolylalkanes, see: Grunert et al. (2004 ▶); Absmeier et al. (2006 ▶); Quesada et al. (2007 ▶); Bialonska et al. (2008 ▶). For a related structure, see: Werner et al. (2009 ▶).

Experimental

Crystal data

[Cu(C9H15N13)2](ClO4)2 M = 873.12 Triclinic, a = 8.5902 (3) Å b = 9.4932 (4) Å c = 11.8446 (5) Å α = 69.233 (1)° β = 74.652 (1)° γ = 71.602 (1)° V = 844.19 (6) Å3 Z = 1 Mo Kα radiation μ = 0.89 mm−1 T = 100 K 0.60 × 0.38 × 0.35 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.86, T max = 1.00 18905 measured reflections 5317 independent reflections 5160 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.026 wR(F 2) = 0.072 S = 1.07 5317 reflections 250 parameters H-atom parameters constrained Δρmax = 0.53 e Å−3 Δρmin = −0.36 e Å−3 Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT, SADABS and XPREP (Bruker, 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008998/bq2196sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008998/bq2196Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Cu(C9H15N13)2](ClO4)2Z = 1
Mr = 873.12F(000) = 447
Triclinic, P1Dx = 1.717 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.5902 (3) ÅCell parameters from 7355 reflections
b = 9.4932 (4) Åθ = 2.4–31.0°
c = 11.8446 (5) ŵ = 0.89 mm−1
α = 69.233 (1)°T = 100 K
β = 74.652 (1)°Prism, blue
γ = 71.602 (1)°0.60 × 0.38 × 0.35 mm
V = 844.19 (6) Å3
Bruker SMART APEX CCD diffractometer5317 independent reflections
Radiation source: normal-focus sealed tube5160 reflections with I > 2σ(I)
graphiteRint = 0.015
φ and ω scansθmax = 31.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −12→12
Tmin = 0.86, Tmax = 1.00k = −13→13
18905 measured reflectionsl = −17→17
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0428P)2 + 0.303P] where P = (Fo2 + 2Fc2)/3
5317 reflections(Δ/σ)max = 0.001
250 parametersΔρmax = 0.53 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cu10.50000.50000.50000.01041 (5)
N10.42188 (10)0.17443 (9)0.37722 (7)0.01129 (14)
N20.58575 (11)0.11927 (10)0.38325 (8)0.01522 (16)
N30.62835 (11)0.21526 (10)0.41688 (8)0.01499 (15)
N40.49368 (10)0.33358 (9)0.43272 (7)0.01173 (14)
N50.23080 (11)0.34128 (10)−0.15509 (8)0.01398 (15)
N60.19378 (16)0.26607 (14)−0.21840 (9)0.0293 (2)
N70.27560 (15)0.30387 (14)−0.32835 (9)0.0271 (2)
N80.36562 (11)0.40410 (10)−0.33836 (8)0.01278 (15)
N90.05800 (10)−0.15980 (9)0.33579 (7)0.01167 (14)
N10−0.01294 (11)−0.20876 (10)0.45440 (8)0.01605 (16)
N110.09776 (11)−0.32341 (11)0.50942 (8)0.01675 (16)
N120.24167 (11)−0.35052 (10)0.42864 (8)0.01439 (15)
N130.19387 (10)0.11244 (9)0.17899 (7)0.01133 (14)
C10.36653 (12)0.30591 (11)0.40781 (9)0.01306 (16)
H10.25570.36870.41120.016*
C20.33577 (12)0.09397 (11)0.33747 (9)0.01269 (16)
H2A0.24190.06500.40260.015*
H2B0.4136−0.00250.32300.015*
C30.27031 (12)0.19884 (11)0.22024 (9)0.01354 (16)
H3A0.18700.29250.23570.016*
H3B0.36290.23270.15620.016*
C40.33503 (12)0.42623 (11)−0.22978 (8)0.01214 (16)
H40.37970.4914−0.20880.015*
C50.16668 (12)0.31649 (11)−0.02381 (9)0.01354 (16)
H5A0.04340.3462−0.00950.016*
H5B0.20540.38230.00630.016*
C60.22876 (12)0.14415 (11)0.04621 (9)0.01244 (16)
H6A0.17550.08110.02430.015*
H6B0.35050.11110.01950.015*
C70.21343 (12)−0.24693 (11)0.32171 (9)0.01360 (16)
H70.2912−0.23650.24720.016*
C8−0.02967 (11)−0.02595 (11)0.24720 (9)0.01210 (16)
H8A−0.1514−0.01190.27490.015*
H8B−0.0011−0.04550.16650.015*
C90.01822 (12)0.12133 (11)0.23426 (9)0.01177 (15)
H9A−0.05250.21220.18250.014*
H9B−0.00210.13600.31610.014*
Cl10.29526 (3)0.69679 (3)0.01464 (2)0.01452 (6)
O10.24265 (13)0.56699 (11)0.10773 (11)0.0356 (2)
O20.35608 (12)0.66142 (13)−0.10061 (10)0.0316 (2)
O30.42605 (10)0.72936 (10)0.04944 (8)0.02103 (16)
O40.15606 (10)0.83116 (9)0.00141 (8)0.02162 (16)
U11U22U33U12U13U23
Cu10.01374 (8)0.01175 (8)0.00772 (8)−0.00612 (6)−0.00085 (5)−0.00332 (5)
N10.0123 (3)0.0121 (3)0.0110 (3)−0.0033 (3)−0.0029 (3)−0.0042 (3)
N20.0129 (4)0.0158 (4)0.0190 (4)−0.0018 (3)−0.0050 (3)−0.0074 (3)
N30.0136 (4)0.0153 (4)0.0181 (4)−0.0028 (3)−0.0040 (3)−0.0070 (3)
N40.0125 (3)0.0134 (3)0.0104 (3)−0.0041 (3)−0.0019 (3)−0.0041 (3)
N50.0185 (4)0.0172 (4)0.0095 (3)−0.0102 (3)−0.0011 (3)−0.0035 (3)
N60.0471 (7)0.0421 (6)0.0132 (4)−0.0352 (5)0.0045 (4)−0.0111 (4)
N70.0437 (6)0.0366 (5)0.0132 (4)−0.0315 (5)0.0040 (4)−0.0091 (4)
N80.0164 (4)0.0140 (3)0.0101 (3)−0.0072 (3)−0.0023 (3)−0.0031 (3)
N90.0117 (3)0.0124 (3)0.0110 (3)−0.0044 (3)−0.0009 (3)−0.0029 (3)
N100.0147 (4)0.0186 (4)0.0122 (4)−0.0052 (3)0.0001 (3)−0.0022 (3)
N110.0160 (4)0.0192 (4)0.0129 (4)−0.0049 (3)−0.0015 (3)−0.0026 (3)
N120.0149 (4)0.0151 (4)0.0128 (4)−0.0031 (3)−0.0029 (3)−0.0040 (3)
N130.0128 (3)0.0144 (3)0.0091 (3)−0.0069 (3)−0.0012 (3)−0.0036 (3)
C10.0133 (4)0.0136 (4)0.0144 (4)−0.0036 (3)−0.0026 (3)−0.0063 (3)
C20.0162 (4)0.0120 (4)0.0126 (4)−0.0052 (3)−0.0049 (3)−0.0037 (3)
C30.0180 (4)0.0141 (4)0.0117 (4)−0.0083 (3)−0.0051 (3)−0.0019 (3)
C40.0144 (4)0.0132 (4)0.0099 (4)−0.0059 (3)−0.0017 (3)−0.0029 (3)
C50.0174 (4)0.0154 (4)0.0083 (4)−0.0066 (3)0.0001 (3)−0.0035 (3)
C60.0148 (4)0.0138 (4)0.0096 (4)−0.0055 (3)−0.0006 (3)−0.0038 (3)
C70.0134 (4)0.0141 (4)0.0128 (4)−0.0025 (3)−0.0017 (3)−0.0045 (3)
C80.0114 (4)0.0120 (4)0.0130 (4)−0.0036 (3)−0.0035 (3)−0.0022 (3)
C90.0126 (4)0.0120 (4)0.0111 (4)−0.0043 (3)−0.0009 (3)−0.0036 (3)
Cl10.01424 (10)0.01325 (10)0.01848 (11)−0.00314 (7)−0.00498 (8)−0.00616 (8)
O10.0351 (5)0.0191 (4)0.0465 (6)−0.0144 (4)−0.0063 (4)0.0039 (4)
O20.0295 (5)0.0418 (5)0.0332 (5)0.0009 (4)−0.0087 (4)−0.0285 (4)
O30.0167 (3)0.0320 (4)0.0204 (4)−0.0103 (3)−0.0048 (3)−0.0099 (3)
O40.0195 (4)0.0178 (3)0.0286 (4)0.0029 (3)−0.0097 (3)−0.0106 (3)
Cu1—N8i2.0210 (8)N13—C61.4579 (12)
Cu1—N8ii2.0210 (8)N13—C31.4617 (12)
Cu1—N42.0259 (8)N13—C91.4656 (12)
Cu1—N4iii2.0259 (8)C1—H10.9500
Cu1—N12iv2.4098 (8)C2—C31.5215 (13)
Cu1—N12v2.4098 (8)C2—H2A0.9900
N1—C11.3305 (12)C2—H2B0.9900
N1—N21.3500 (11)C3—H3A0.9900
N1—C21.4657 (12)C3—H3B0.9900
N2—N31.2915 (12)C4—H40.9500
N3—N41.3599 (12)C5—C61.5395 (13)
N4—C11.3249 (12)C5—H5A0.9900
N5—C41.3286 (12)C5—H5B0.9900
N5—N61.3500 (12)C6—H6A0.9900
N5—C51.4649 (12)C6—H6B0.9900
N6—N71.2892 (13)C7—H70.9500
N7—N81.3614 (12)C8—H8A0.9900
N8—C41.3210 (12)C8—H8B0.9900
N8—Cu1vi2.0209 (8)C9—C81.5248 (13)
N9—C71.3332 (12)C9—H9A0.9900
N9—N101.3505 (11)C9—H9B0.9900
N9—C81.4668 (12)Cl1—O11.4362 (9)
N10—N111.2982 (12)Cl1—O41.4409 (8)
N11—N121.3630 (12)Cl1—O31.4430 (8)
N12—C71.3262 (12)Cl1—O21.4442 (10)
N12—Cu1vii2.4098 (8)
N8i—Cu1—N8ii180.0C3—C2—H2A109.7
N8i—Cu1—N489.54 (3)N1—C2—H2B109.7
N8ii—Cu1—N490.46 (3)C3—C2—H2B109.7
N8i—Cu1—N4iii90.46 (3)H2A—C2—H2B108.2
N8ii—Cu1—N4iii89.54 (3)N13—C3—C2108.77 (7)
N4—Cu1—N4iii180.0N13—C3—H3A109.9
N8i—Cu1—N12iv88.33 (3)C2—C3—H3A109.9
N8ii—Cu1—N12iv91.67 (3)N13—C3—H3B109.9
N4—Cu1—N12iv92.20 (3)C2—C3—H3B109.9
N4iii—Cu1—N12iv87.80 (3)H3A—C3—H3B108.3
N8i—Cu1—N12v91.67 (3)N8—C4—N5108.02 (8)
N8ii—Cu1—N12v88.33 (3)N8—C4—H4126.0
N4—Cu1—N12v87.80 (3)N5—C4—H4126.0
N4iii—Cu1—N12v92.20 (3)N5—C5—C6109.51 (8)
N12iv—Cu1—N12v180.0N5—C5—H5A109.8
C1—N1—N2108.62 (8)C6—C5—H5A109.8
C1—N1—C2130.53 (8)N5—C5—H5B109.8
N2—N1—C2120.81 (8)C6—C5—H5B109.8
N3—N2—N1107.19 (8)H5A—C5—H5B108.2
N2—N3—N4109.54 (8)N13—C6—C5113.54 (8)
C1—N4—N3106.88 (8)N13—C6—H6A108.9
C1—N4—Cu1130.20 (7)C5—C6—H6A108.9
N3—N4—Cu1122.61 (6)N13—C6—H6B108.9
C4—N5—N6108.65 (8)C5—C6—H6B108.9
C4—N5—C5129.94 (8)H6A—C6—H6B107.7
N6—N5—C5121.31 (8)N12—C7—N9108.87 (9)
N7—N6—N5106.93 (9)N12—C7—H7125.6
N6—N7—N8109.82 (9)N9—C7—H7125.6
C4—N8—N7106.58 (8)N9—C8—C9110.61 (7)
C4—N8—Cu1vi131.67 (7)N9—C8—H8A109.5
N7—N8—Cu1vi121.62 (7)C9—C8—H8A109.5
C7—N9—N10108.17 (8)N9—C8—H8B109.5
C7—N9—C8129.90 (8)C9—C8—H8B109.5
N10—N9—C8121.83 (8)H8A—C8—H8B108.1
N11—N10—N9106.94 (8)N13—C9—C8111.13 (8)
N10—N11—N12110.25 (8)N13—C9—H9A109.4
C7—N12—N11105.77 (8)C8—C9—H9A109.4
C7—N12—Cu1vii130.45 (7)N13—C9—H9B109.4
N11—N12—Cu1vii120.86 (6)C8—C9—H9B109.4
C6—N13—C3112.76 (7)H9A—C9—H9B108.0
C6—N13—C9114.58 (7)O1—Cl1—O4109.30 (6)
C3—N13—C9113.41 (8)O1—Cl1—O3109.62 (6)
N4—C1—N1107.78 (8)O4—Cl1—O3109.26 (5)
N4—C1—H1126.1O1—Cl1—O2109.78 (7)
N1—C1—H1126.1O4—Cl1—O2109.38 (6)
N1—C2—C3110.04 (7)O3—Cl1—O2109.49 (6)
N1—C2—H2A109.7
C1—N1—N2—N30.07 (11)N2—N1—C1—N40.06 (11)
C2—N1—N2—N3178.01 (8)C2—N1—C1—N4−177.61 (9)
N1—N2—N3—N4−0.17 (11)C1—N1—C2—C360.09 (13)
N2—N3—N4—C10.21 (11)N2—N1—C2—C3−117.34 (9)
N2—N3—N4—Cu1174.39 (7)C6—N13—C3—C2−140.77 (8)
N8i—Cu1—N4—C1−113.40 (9)C9—N13—C3—C286.92 (10)
N8ii—Cu1—N4—C166.60 (9)N1—C2—C3—N13176.71 (8)
N12iv—Cu1—N4—C1158.29 (9)N7—N8—C4—N50.55 (12)
N12v—Cu1—N4—C1−21.71 (9)Cu1vi—N8—C4—N5176.20 (7)
N8i—Cu1—N4—N373.91 (8)N6—N5—C4—N8−0.77 (12)
N8ii—Cu1—N4—N3−106.09 (8)C5—N5—C4—N8175.60 (9)
N12iv—Cu1—N4—N3−14.40 (8)C4—N5—C5—C6−115.73 (11)
N12v—Cu1—N4—N3165.60 (8)N6—N5—C5—C660.24 (13)
C4—N5—N6—N70.68 (15)C3—N13—C6—C5−59.54 (10)
C5—N5—N6—N7−176.05 (11)C9—N13—C6—C572.20 (10)
N5—N6—N7—N8−0.34 (16)N5—C5—C6—N13170.74 (7)
N6—N7—N8—C4−0.13 (14)C6—N13—C9—C879.11 (9)
N6—N7—N8—Cu1vi−176.32 (9)C3—N13—C9—C8−149.46 (8)
C7—N9—N10—N11−0.45 (11)C7—N9—C8—C9−80.18 (12)
C8—N9—N10—N11−177.15 (8)N10—N9—C8—C995.73 (10)
N9—N10—N11—N120.29 (11)N13—C9—C8—N966.24 (10)
N10—N11—N12—C7−0.02 (11)N11—N12—C7—N9−0.27 (11)
N10—N11—N12—Cu1vii162.54 (7)Cu1vii—N12—C7—N9−160.50 (7)
N3—N4—C1—N1−0.17 (11)N10—N9—C7—N120.45 (11)
Cu1—N4—C1—N1−173.74 (6)C8—N9—C7—N12176.79 (9)
D—H···AD—HH···AD···AD—H···A
C2—H2A···N10viii0.992.603.366 (2)134
C4—H4···O20.952.333.191 (2)151
C5—H5B···O10.992.583.557 (2)168
C6—H6A···O4vii0.992.543.459 (2)154
C7—H7···O3vii0.952.413.305 (2)157
C8—H8A···N2ix0.992.473.361 (2)149
C8—H8B···O4vii0.992.503.440 (2)159
C8—H8B···O4x0.992.593.136 (2)115
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2A⋯N10i0.992.603.366 (2)134
C4—H4⋯O20.952.333.191 (2)151
C5—H5B⋯O10.992.583.557 (2)168
C6—H6A⋯O4ii0.992.543.459 (2)154
C7—H7⋯O3ii0.952.413.305 (2)157
C8—H8A⋯N2iii0.992.473.361 (2)149
C8—H8B⋯O4ii0.992.503.440 (2)159
C8—H8B⋯O4iv0.992.593.136 (2)115

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

  6 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.  (1R,2R)-1,2-Diphenyl-1,2-bis-(1H-tetra-zol-1-yl)ethane.

Authors:  Franz Werner; Kurt Mereiter; Kenji Tokuno; Yuki Inagaki; Miki Hasegawa
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-10-13

4.  [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

5.  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

6.  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
  6 in total

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