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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): m238.
Published online 2007 December 21. doi:  10.1107/S1600536807066846
PMCID: PMC2915158

Bis(2,2′-bipyridine)(5,5′-imino­ditetra­zolato)cadmium(II) 2,2′-bipyridine hemisolvate monohydrate

Abstract

The title complex, [Cd(C2HN9)(C10H8N2)2]·0.5C10H8N2·H2O, was prepared under hydro­thermal reaction conditions. The asymmetric unit contains the cadmium complex, half a 2,2′-bipyridine solvent mol­ecule and a solvent water mol­ecule. The CdII ion is coordinated by four N atoms from two 2,2′-bipyridine ligands and two N atoms from an HBTA anion ligand [where H2BTA is N,N-bis­(1H-tetra­zol-5-yl)amine], forming an octa­hedral geometry. The complex is linked into a three-dimensional network by O—H(...)N and N—H(...)N hydrogen bonds and by the stacking inter­actions of rings, with distances of 3.5–3.7 Å between the atoms of two parallel 2,2′-bipyridine rings.

Related literature

Other complexes of the N,N-bis-[1(2)H-tetra­zol-5-yl]imine ligand are rare; for a related copper(II) complex, see: Friedrich et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m238-scheme1.jpg

Experimental

Crystal data

  • [Cd(C2HN9)(C10H8N2)2]·0.5C10H8N2·H2O
  • M r = 672.00
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m238-efi1.jpg
  • a = 15.1919 (12) Å
  • b = 11.2383 (9) Å
  • c = 17.5759 (14) Å
  • β = 106.073 (3)°
  • V = 2883.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.81 mm−1
  • T = 296 (2) K
  • 0.24 × 0.23 × 0.13 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.824, T max = 0.901
  • 41852 measured reflections
  • 6569 independent reflections
  • 5669 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.064
  • S = 1.07
  • 6569 reflections
  • 477 parameters
  • All H-atom parameters refined
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT-Plus (Bruker, 2005 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 2005 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066846/bq2057sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066846/bq2057Isup2.hkl

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

Acknowledgments

The authors acknowledge financial support by the National Natural Science Foundation of China (grant No. 206710214), and the Science and Technology Program Foundation of Guang Zhou (2007 J1-co381).

supplementary crystallographic information

Comment

The H2BTA (where H2BTA is N,N-bis(1(2)H-tetrazol-5-yl)-amine) and its deprotonated anions contain nine nitrogen electron-donating atoms and show hundreds of different coordinating or bridging modes in their complexes. However, the complexes of H2BTA ligand have been not widely investigated in past decades (Friedrich et al., 2005). The title complex, (I), consists of the cadmium complex of 2,2'-bipyridine and HBTA- anion ligands, half 2,2'-bipyridine guest molecule and a solvent water molecule (Fig. 1). The HBTA- ligand acts as a chelatingbidentate and the CdII cation is coordinated to four N atoms from two 2,2'-bipyridine ligands and two N atoms from a HBTA- anion ligand to form an octahedral mononuclear complex. In the crystal structure, an extensive range of O—H···N and N—H···N hydrogen bonds as well as the stacking interactions of aryls between the parallel 2,2'-bipyridine molecules links the complex, 2,2'-bipyridine guest molecules and the water molecules into a three dimensional networks (Table 1 and Fig. 2).

Experimental

A 20 mL aqueous solution of Cd(Cl)2.4H2O (0.026 g, 0.1 mmol), H2BTA (0.016 g, 0.01 mmol) and 2,2'-bipyridine (0.039 g, 0.025 mmol) was heated in a 25 ml Teflon-lined autoclave at 433 K for 3 d, followed by slow cooling to room temperature. The resulting mixture was filtered and washed with 95% methanol, and colorless crystal were collected and dried in air. Elemental analysis, calc (%) for C27H23Cd1N14O1: C 48.21, H 3.42, N 27.08; found (%): C 47.96, H 3.87, N 26.78.

Refinement

All hydrogen atoms were located in difference Fourier maps and freely refined with isotropic displacement parameters.

Figures

Fig. 1.
The molecular structure of the complex, with atom labels and 30% probability displacement ellipsoids for non-H atoms. Symmetry code (i): -x, -y, -z.
Fig. 2.
The packing diagram of the complex, showing a three-dimensional network connected by O—H···N and N—H···N hydrogen bonds (dashed lines) and by the stacking interactions of aryls between the ...

Crystal data

[Cd(C2HN9)(C10H8N2)2]·0.5C10H8N2·H2OF000 = 1356
Mr = 672.00Dx = 1.548 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P2ynCell parameters from 6569 reflections
a = 15.1919 (12) Åθ = 27.5–1.0º
b = 11.2383 (9) ŵ = 0.81 mm1
c = 17.5759 (14) ÅT = 296 (2) K
β = 106.073 (3)ºBlock, colourless
V = 2883.5 (4) Å30.24 × 0.23 × 0.13 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer6569 independent reflections
Radiation source: fine-focus sealed tube5669 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 296(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −19→19
Tmin = 0.824, Tmax = 0.901k = −14→14
41852 measured reflectionsl = −21→22

Refinement

Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.025  w = 1/[σ2(Fo2) + (0.0274P)2 + 0.9028P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.064(Δ/σ)max = 0.003
S = 1.07Δρmax = 0.27 e Å3
6569 reflectionsΔρmin = −0.30 e Å3
477 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00357 (18)
Secondary atom site location: difference Fourier map

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.

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

xyzUiso*/Ueq
Cd10.532267 (9)0.270422 (13)0.774688 (8)0.04977 (6)
N10.53723 (11)0.28970 (14)0.64584 (10)0.0532 (4)
N20.56948 (13)0.20365 (15)0.60598 (11)0.0626 (4)
N60.49834 (12)0.46846 (15)0.74874 (10)0.0562 (4)
N30.56653 (15)0.24290 (15)0.53653 (11)0.0669 (5)
N50.48085 (12)0.48791 (16)0.60938 (11)0.0576 (4)
N90.47554 (13)0.64671 (15)0.69592 (11)0.0663 (5)
N80.48433 (14)0.65384 (17)0.77468 (12)0.0714 (5)
N40.53314 (12)0.35578 (15)0.52681 (9)0.0592 (4)
N70.49775 (13)0.54972 (17)0.80637 (11)0.0652 (4)
C10.51621 (12)0.38009 (16)0.59524 (10)0.0479 (4)
C20.48555 (12)0.53204 (16)0.68325 (11)0.0495 (4)
N100.45883 (14)0.27233 (15)0.87647 (11)0.0621 (4)
N120.68118 (11)0.31927 (17)0.85200 (11)0.0624 (4)
N110.39018 (11)0.17392 (15)0.73247 (11)0.0594 (4)
N130.62379 (11)0.09995 (15)0.79609 (10)0.0553 (4)
C70.37105 (17)0.23839 (18)0.85718 (15)0.0639 (6)
C170.74399 (14)0.2331 (2)0.86491 (13)0.0602 (5)
C120.36175 (15)0.1183 (2)0.66307 (16)0.0735 (6)
C80.33420 (13)0.18067 (18)0.77886 (14)0.0606 (5)
C180.71146 (13)0.1114 (2)0.83875 (12)0.0579 (5)
C160.83514 (18)0.2601 (3)0.9003 (2)0.0903 (9)
C60.3187 (3)0.2561 (3)0.9092 (2)0.0921 (9)
C30.4959 (2)0.3204 (3)0.94745 (15)0.0824 (7)
C110.27651 (18)0.0677 (3)0.6357 (2)0.0915 (9)
C220.59252 (17)−0.0076 (2)0.77108 (16)0.0703 (6)
C140.79708 (19)0.4612 (3)0.90888 (19)0.0904 (8)
C150.8608 (2)0.3740 (3)0.9222 (2)0.1035 (10)
C90.24676 (18)0.1321 (3)0.7531 (2)0.0864 (8)
C130.70807 (17)0.4305 (2)0.87371 (17)0.0808 (7)
C190.76731 (19)0.0129 (3)0.8578 (2)0.0885 (8)
C100.21877 (19)0.0756 (3)0.6815 (2)0.0998 (10)
C40.4464 (4)0.3369 (3)1.00196 (19)0.1007 (11)
C210.6447 (2)−0.1090 (2)0.7879 (2)0.0860 (8)
C50.3577 (3)0.3043 (3)0.9816 (2)0.1103 (12)
C200.7331 (2)−0.0975 (3)0.8319 (2)0.1006 (10)
O10.40434 (19)0.8585 (2)0.60636 (19)0.1105 (8)
C280.54281 (19)0.0235 (2)0.02531 (14)0.0757 (6)
C270.5463 (2)0.0710 (2)0.09726 (16)0.0844 (7)
H210.49380.07430.11470.101*
C260.6255 (3)0.1129 (3)0.1425 (2)0.1115 (11)
C250.7028 (3)0.1084 (3)0.1179 (2)0.1102 (11)
N140.6182 (2)0.0168 (2)−0.00166 (16)0.1035 (8)
H10.4760 (15)0.533 (2)0.5756 (13)0.062 (7)*
H90.4053 (16)0.116 (2)0.6320 (13)0.072 (7)*
H60.2165 (19)0.139 (2)0.7846 (16)0.087 (9)*
H70.158 (2)0.044 (3)0.6619 (17)0.106 (9)*
H80.260 (2)0.026 (3)0.5852 (19)0.121 (11)*
H20.5629 (19)0.338 (3)0.9605 (16)0.096 (9)*
H40.323 (2)0.316 (3)1.021 (2)0.131 (11)*
H50.259 (2)0.233 (3)0.894 (2)0.105 (11)*
H30.475 (2)0.365 (3)1.0450 (19)0.098 (10)*
H170.5337 (17)−0.013 (2)0.7381 (14)0.074 (7)*
H130.874 (2)0.201 (3)0.9080 (16)0.088 (9)*
H110.8101 (19)0.542 (3)0.9196 (16)0.100 (9)*
H100.6577 (19)0.491 (2)0.8614 (16)0.095 (9)*
H160.6172 (18)−0.179 (3)0.7664 (16)0.089 (8)*
H150.769 (2)−0.165 (3)0.8439 (19)0.121 (11)*
H120.923 (2)0.395 (3)0.9494 (19)0.126 (11)*
H140.828 (2)0.027 (3)0.8895 (18)0.108 (10)*
H200.632 (2)0.143 (3)0.194 (2)0.130 (13)*
H190.764 (2)0.129 (3)0.150 (2)0.125 (12)*
C240.6980 (3)0.0596 (4)0.0460 (2)0.1138 (11)
H220.421 (3)0.801 (4)0.635 (2)0.123 (14)*
H230.398 (3)0.830 (4)0.556 (3)0.163 (17)*
H180.747 (2)0.040 (3)0.0236 (19)0.113 (11)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.04460 (8)0.04959 (9)0.05279 (9)0.00138 (5)0.00960 (6)−0.00035 (6)
N10.0591 (9)0.0464 (9)0.0542 (9)0.0083 (7)0.0155 (7)−0.0006 (7)
N20.0781 (12)0.0494 (9)0.0594 (10)0.0113 (8)0.0176 (9)−0.0033 (7)
N60.0640 (10)0.0518 (9)0.0536 (9)0.0071 (8)0.0176 (7)−0.0036 (7)
N30.0874 (14)0.0537 (10)0.0578 (11)0.0134 (9)0.0172 (9)−0.0073 (8)
N50.0724 (11)0.0490 (9)0.0507 (10)0.0141 (8)0.0161 (8)0.0047 (8)
N90.0865 (12)0.0474 (9)0.0725 (11)0.0051 (8)0.0345 (10)−0.0034 (8)
N80.0873 (13)0.0584 (11)0.0757 (13)0.0026 (9)0.0346 (10)−0.0135 (9)
N40.0760 (11)0.0510 (9)0.0475 (9)0.0117 (8)0.0117 (8)−0.0035 (7)
N70.0777 (12)0.0613 (11)0.0613 (10)0.0061 (9)0.0270 (9)−0.0092 (8)
C10.0464 (9)0.0465 (10)0.0471 (10)0.0024 (7)0.0070 (7)−0.0037 (7)
C20.0452 (9)0.0479 (10)0.0574 (11)0.0037 (7)0.0173 (8)−0.0024 (8)
N100.0755 (12)0.0562 (10)0.0570 (10)0.0062 (8)0.0224 (9)0.0046 (8)
N120.0481 (9)0.0621 (10)0.0714 (11)−0.0040 (8)0.0073 (8)−0.0030 (9)
N110.0478 (8)0.0524 (9)0.0789 (12)0.0007 (7)0.0189 (8)−0.0104 (8)
N130.0517 (9)0.0550 (9)0.0579 (9)0.0049 (7)0.0129 (7)0.0045 (7)
C70.0736 (14)0.0490 (11)0.0790 (15)0.0158 (10)0.0377 (12)0.0169 (10)
C170.0468 (10)0.0762 (14)0.0556 (11)0.0014 (9)0.0107 (8)0.0070 (10)
C120.0545 (12)0.0710 (15)0.0938 (17)−0.0029 (10)0.0184 (12)−0.0273 (13)
C80.0520 (10)0.0483 (10)0.0850 (15)0.0097 (9)0.0247 (10)0.0091 (10)
C180.0489 (10)0.0693 (13)0.0558 (11)0.0089 (9)0.0152 (8)0.0094 (9)
C160.0484 (13)0.103 (2)0.108 (2)0.0046 (13)0.0014 (13)0.0003 (17)
C60.105 (2)0.0825 (19)0.109 (3)0.0165 (16)0.064 (2)0.0100 (16)
C30.110 (2)0.0793 (17)0.0581 (14)0.0035 (16)0.0240 (14)0.0028 (12)
C110.0566 (13)0.0860 (19)0.123 (2)−0.0047 (12)0.0092 (15)−0.0384 (17)
C220.0635 (13)0.0597 (13)0.0857 (16)0.0034 (10)0.0174 (12)0.0001 (11)
C140.0697 (16)0.088 (2)0.102 (2)−0.0256 (15)0.0054 (14)−0.0134 (16)
C150.0550 (14)0.122 (3)0.118 (2)−0.0214 (17)−0.0017 (15)−0.013 (2)
C90.0552 (13)0.0894 (19)0.122 (2)0.0056 (12)0.0370 (15)0.0111 (17)
C130.0613 (14)0.0732 (16)0.0964 (19)−0.0095 (12)0.0028 (13)−0.0129 (13)
C190.0597 (14)0.0825 (19)0.117 (2)0.0207 (13)0.0145 (15)0.0136 (16)
C100.0529 (14)0.091 (2)0.148 (3)−0.0109 (13)0.0150 (17)−0.0166 (19)
C40.169 (4)0.0783 (19)0.0608 (17)0.014 (2)0.041 (2)0.0034 (14)
C210.0878 (19)0.0567 (15)0.120 (2)0.0085 (13)0.0395 (17)0.0005 (14)
C50.162 (4)0.095 (2)0.103 (3)0.022 (2)0.085 (3)0.0110 (19)
C200.0833 (19)0.0758 (19)0.143 (3)0.0311 (16)0.0323 (19)0.0184 (18)
O10.146 (2)0.0835 (14)0.1159 (19)0.0489 (14)0.0601 (16)−0.0008 (14)
C280.110 (2)0.0503 (12)0.0725 (16)0.0102 (12)0.0343 (13)0.0153 (10)
C270.113 (2)0.0722 (16)0.0732 (16)0.0032 (15)0.0348 (16)−0.0052 (13)
C260.155 (4)0.087 (2)0.098 (3)−0.002 (2)0.043 (3)−0.0129 (19)
C250.130 (3)0.093 (2)0.101 (3)−0.022 (2)0.020 (2)−0.0030 (19)
N140.130 (2)0.0973 (18)0.0890 (17)0.0021 (17)0.0396 (17)0.0085 (14)
C240.123 (3)0.115 (3)0.112 (3)−0.008 (2)0.046 (2)0.006 (2)

Geometric parameters (Å, °)

Cd1—N12.2970 (17)C6—C51.358 (5)
Cd1—N62.3015 (17)C6—H50.91 (3)
Cd1—N132.3357 (16)C3—C41.384 (4)
Cd1—N112.3451 (16)C3—H21.00 (3)
Cd1—N102.3559 (18)C11—C101.348 (5)
Cd1—N122.3587 (16)C11—H80.97 (3)
N1—C11.329 (2)C22—C211.373 (3)
N1—N21.362 (2)C22—H170.92 (2)
N2—N31.287 (3)C14—C151.352 (5)
N6—C21.322 (2)C14—C131.366 (3)
N6—N71.366 (2)C14—H110.93 (3)
N3—N41.359 (2)C15—H120.96 (3)
N5—C21.373 (2)C9—C101.367 (5)
N5—C11.376 (2)C9—H60.82 (3)
N5—H10.77 (2)C13—H101.00 (3)
N9—C21.324 (3)C19—C201.373 (4)
N9—N81.356 (3)C19—H140.95 (3)
N8—N71.288 (3)C10—H70.96 (3)
N4—C11.326 (2)C4—C51.346 (5)
N10—C31.333 (3)C4—H30.82 (3)
N10—C71.337 (3)C21—C201.357 (4)
N12—C171.334 (3)C21—H160.92 (3)
N12—C131.338 (3)C5—H40.98 (4)
N11—C121.332 (3)C20—H150.92 (3)
N11—C81.333 (3)O1—H220.82 (4)
N13—C221.328 (3)O1—H230.92 (4)
N13—C181.341 (2)C28—N141.357 (4)
C7—C61.382 (4)C28—C271.361 (3)
C7—C81.484 (3)C28—C28i1.456 (5)
C17—C161.386 (3)C27—C261.332 (5)
C17—C181.483 (3)C27—H210.9300
C12—C111.373 (3)C26—C251.360 (5)
C12—H90.97 (2)C26—H200.94 (4)
C8—C91.391 (3)C25—C241.361 (5)
C18—C191.378 (3)C25—H190.97 (3)
C16—C151.362 (5)N14—C241.357 (5)
C16—H130.88 (3)C24—H180.96 (3)
N1—Cd1—N677.29 (6)C15—C16—C17120.4 (3)
N1—Cd1—N1393.18 (6)C15—C16—H13123.0 (19)
N6—Cd1—N13156.31 (6)C17—C16—H13117 (2)
N1—Cd1—N1190.59 (6)C5—C6—C7119.7 (4)
N6—Cd1—N11104.39 (6)C5—C6—H5122 (2)
N13—Cd1—N1197.26 (6)C7—C6—H5119 (2)
N1—Cd1—N10154.10 (7)N10—C3—C4122.2 (3)
N6—Cd1—N1090.83 (6)N10—C3—H2115.7 (16)
N13—Cd1—N10105.73 (6)C4—C3—H2122.0 (16)
N11—Cd1—N1069.92 (7)C10—C11—C12118.0 (3)
N1—Cd1—N12104.95 (6)C10—C11—H8122 (2)
N6—Cd1—N1290.89 (6)C12—C11—H8120 (2)
N13—Cd1—N1270.42 (6)N13—C22—C21123.5 (2)
N11—Cd1—N12160.38 (7)N13—C22—H17117.5 (15)
N10—Cd1—N1298.09 (7)C21—C22—H17118.9 (16)
C1—N1—N2104.62 (16)C15—C14—C13117.9 (3)
C1—N1—Cd1131.62 (12)C15—C14—H11124.4 (18)
N2—N1—Cd1123.69 (12)C13—C14—H11117.6 (18)
N3—N2—N1108.74 (16)C14—C15—C16119.8 (3)
C2—N6—N7104.75 (16)C14—C15—H12118 (2)
C2—N6—Cd1131.75 (13)C16—C15—H12122 (2)
N7—N6—Cd1123.14 (13)C10—C9—C8120.5 (3)
N2—N3—N4110.66 (16)C10—C9—H6125 (2)
C2—N5—C1124.64 (17)C8—C9—H6114 (2)
C2—N5—H1117.6 (18)N12—C13—C14123.4 (3)
C1—N5—H1113.5 (18)N12—C13—H10114.6 (16)
C2—N9—N8104.23 (17)C14—C13—H10122.0 (16)
N7—N8—N9110.31 (16)C20—C19—C18119.6 (3)
C1—N4—N3103.75 (16)C20—C19—H14124.2 (19)
N8—N7—N6108.63 (17)C18—C19—H14116 (2)
N4—C1—N1112.23 (16)C11—C10—C9119.5 (3)
N4—C1—N5121.93 (17)C11—C10—H7118.7 (18)
N1—C1—N5125.85 (17)C9—C10—H7121.8 (18)
N6—C2—N9112.07 (17)C5—C4—C3118.3 (3)
N6—C2—N5125.76 (17)C5—C4—H3125 (2)
N9—C2—N5122.17 (18)C3—C4—H3116 (2)
C3—N10—C7119.1 (2)C20—C21—C22117.7 (3)
C3—N10—Cd1123.25 (19)C20—C21—H16125.4 (17)
C7—N10—Cd1116.97 (15)C22—C21—H16116.9 (18)
C17—N12—C13118.86 (19)C4—C5—C6120.2 (3)
C17—N12—Cd1117.10 (14)C4—C5—H4118 (2)
C13—N12—Cd1123.39 (16)C6—C5—H4122 (2)
C12—N11—C8119.13 (19)C21—C20—C19119.9 (3)
C12—N11—Cd1122.94 (15)C21—C20—H15119 (2)
C8—N11—Cd1117.85 (14)C19—C20—H15121 (2)
C22—N13—C18118.75 (19)H22—O1—H23104 (4)
C22—N13—Cd1123.41 (14)N14—C28—C27121.8 (3)
C18—N13—Cd1117.78 (14)N14—C28—C28i117.6 (3)
N10—C7—C6120.5 (3)C27—C28—C28i120.5 (3)
N10—C7—C8116.96 (19)C26—C27—C28119.3 (3)
C6—C7—C8122.6 (3)C26—C27—H21120.3
N12—C17—C16119.7 (2)C28—C27—H21120.3
N12—C17—C18117.10 (18)C27—C26—C25121.0 (4)
C16—C17—C18123.2 (2)C27—C26—H20123 (2)
N11—C12—C11123.4 (3)C25—C26—H20116 (2)
N11—C12—H9115.5 (14)C26—C25—C24118.7 (4)
C11—C12—H9121.1 (14)C26—C25—H19126 (2)
N11—C8—C9119.5 (2)C24—C25—H19115 (2)
N11—C8—C7116.84 (19)C28—N14—C24117.4 (3)
C9—C8—C7123.7 (2)N14—C24—C25121.7 (4)
N13—C18—C19120.5 (2)N14—C24—H18109 (2)
N13—C18—C17117.10 (18)C25—C24—H18129 (2)
C19—C18—C17122.3 (2)

Symmetry codes: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N5—H1···N4ii0.77 (2)2.17 (2)2.929 (2)174 (2)
O1—H22···N90.82 (4)2.08 (4)2.893 (3)172 (4)
O1—H23···N3ii0.92 (4)2.02 (5)2.901 (3)159 (4)

Symmetry codes: (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2057).

References

  • Bruker (2005). SAINT-Plus (Version 6.45), SHELXTL (Version 6.14) and SMART (Version 5.054). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Friedrich, M., Gólvez-Ruiz, J. C., Klapötke, T. M., Mayer, P., Weber, R. & Weigand, J. J. (2005). Inorg. Chem.44, 8044–8052. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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