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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160505
doi:10.1107/S2414314616005058

(4,7,13,16,21,24-Hexaoxa-1,10-di­aza­bi­cyclo[8.8.8]hexa­cosane-κ8N2,O6)rubidium 4,4′-bipyridinid­yl

Kerstin Mayer,a Wilhelm Kleina and Thomas F. Fässlera*

aTechnische Universität München, Department of Chemistry, Lichtenbergstrasse 4, 85747 Garching, Germany
*Correspondence e-mail: thomas.faessler@lrz.tu-muenchen.de

Edited by M. Weil, Vienna University of Technology, Austria (Received 9 March 2016; accepted 24 March 2016; online 31 March 2016)

The crystal structure of the title salt, [Rb(C18H36N2O6)](C10H8N2), consists of Rb+ cations sequestered by a [2.2.2]cryptand mol­ecule and 4,4′-bipyridinidyl radical monoanions. Both entities are centred by special positions: the Rb+ cation is located on a twofold rotation axis and the 4,4′-bipyridinidyl anion is located about an inversion centre, so half of each moiety form the asymmetric unit. The planar 4,4′-bipyridinidyl mol­ecules and the complexed cations are arranged in the sense of a distorted rock salt type of structure.

CCDC reference: 1470480

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

From the reaction of pyridine with alkali metals, it is known that pyridine undergoes a coupling reaction to 4,4′-bi­pyridine which leads to the corresponding radical monoanion (Ward, 1961[Ward, R. L. (1961). J. Am. Chem. Soc. 83, 3623-3626.]; Schmulbach et al., 1968[Schmulbach, C. D., Hinckley, C. C. & Wasmund, D. (1968). J. Am. Chem. Soc. 90, 6600-6602.]). Recently, we have investigated the same species after reaction of the Zintl phase K12Si17 with pyridine (Benda & Fässler, 2014[Benda, C. & Fässler, T. F. (2014). Z. Naturforsch. Teil B, 69, 1119-1123.]). During our recent experiments with pyridine, we found Rb12Si17 also works as a reducing agent, leading to 4,4′-bipyridinidyl radical monoanions. Due to inversion symmetry, the bipyridinidyl mol­ecule in the title compound is planar (Fig. 1[link]). The C—C distances range between 1.368 (3) and 1.431 (3) Å and the C—N distances are 1.353 (3) and 1.354 (3) Å, which agree well with those of previously reported compounds (Benda & Fässler, 2014[Benda, C. & Fässler, T. F. (2014). Z. Naturforsch. Teil B, 69, 1119-1123.]; Denning et al., 2008[Denning, M. S., Irwin, M. & Goicoechea, J. M. (2008). Inorg. Chem. 47, 6118-6120.]). In the crystal, the mol­ecular entities are arranged in a rock salt type of structure (Figs. 2[link] and 3[link]).

[Figure 1]
Figure 1
Mol­ecular entities of the title compound. Anisotropic displacement ellipsoids are drawn at the 70% probability level. [Symmetry codes: (i) −x + [{3\over 2}], y, −z + [{1\over 2}]; (ii) −x, −y + 1, −z.]
[Figure 2]
Figure 2
Part of the crystal structure in a view along [100]. Anisotropic displacement ellipsoids are drawn at the 70% probability level, H atoms are omitted for clarity.
[Figure 3]
Figure 3
Distorted rock salt type packing of the entities in the title compound. H atoms and cryptand mol­ecules are omitted for clarity.

Synthesis and crystallization

All manipulations were carried out under an argon atmos­phere using standard Schlenk and glove-box techniques. Cryptand [2.2.2] was dried in vacuo. Anhydrous pyridine (VWR) was stored over a mol­ecular sieve in an argon-filled glove box. Toluene was dried over a mol­ecular sieve (4 Å) in a solvent purificater (MBraun, MB-SPS). Liquid ammonia was stored over elemental Na for one day and freshly distilled before use. Rb12Si17 was prepared from a stoichiometric mixtures of 557 mg (6.52 mmol) Rb and 259 mg (9.23 mmol) Si sealed in a tantalum container, which was encapsulated in an evacuated fused silica tube and heated to 1073 K (2 K min−1) for 15 h and slowly cooled to room temperature at a rate of 0.5 K min−1.

Rb12Si17 (90.2 mg; 60 µmol) and cryptand [2.2.2] (127 mg; 337 µmol) were weighed into a Schlenk tube. 2 ml of liquid ammonia were condensed to the reactants, leading to a deep-red solution. The mixture was stirred for 4 h at 195 K, after that time the liquid ammonia was evaporated. The residue was dissolved in 3 ml of anhydrous pyridine and stirred overnight at room temperature. The resulting deep-purple solution was filtered and layered with 4 ml toluene. The title compound crystallized as deep purple/black plates and was isolated after 7 months.

The very air- and moisture-sensitive crystals were transferred from the mother liquor into perfluoro­polyalkyl ether oil inside a glove box. Single crystals were fixed on a glass capillary and positioned in a 100 K cold N2 stream.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1[link]. The highest and lowest remaining electron densities are located at 0.99 Å and at 0.80 Å from the Rb site, respectively.

Table 1
Experimental details

Crystal data
Chemical formula [Rb(C18H36N2O6)](C10H8N2)
Mr 618.14
Crystal system, space group Monoclinic, P2/n
Temperature (K) 100
a, b, c (Å) 11.2326 (4), 8.0250 (3), 16.3653 (7)
β (°) 91.950 (3)
V (Å3) 1474.34 (10)
Z 2
Radiation type Mo Kα
μ (mm−1) 1.73
Crystal size (mm) 0.25 × 0.20 × 0.15
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]).
Tmin, Tmax 0.617, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 12998, 2895, 2530
Rint 0.040
(sin θ/λ)max (Å−1) 0.617
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.065, 1.04
No. of reflections 2895
No. of parameters 265
H-atom treatment All H-atom parameters refined
Δρmax, Δρmin (e Å−3) 0.54, −0.33
Computer programs: APEX2 and SAINT (Bruker, 2012[Bruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2014 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND . Crystal Impact GbR, Bonn, Germany.]).

Structural data

CCDC reference: 1470480

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616005058/wm4010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616005058/wm4010Isup2.hkl

checkCIF report


Experimental top

All manipulations were carried out under an argon atmosphere using standard Schlenk and glove-box techniques. Cryptand [2.2.2] was dried in vacuo. Anhydrous pyridine (VWR) was stored over a molecular sieve in an argon-filled glove box. Toluene was dried over a molecular sieve (4 Å) in a solvent purificater (MBraun, MB-SPS). Liquid ammonia was stored over elemental Na for one day and freshly distilled before use. Rb12Si17 was prepared from a stoichiometric mixtures of 557 mg (6.52 mmol) Rb and 259 mg (9.23 mmol) Si sealed in a tantalum container, which was encapsulated in an evacuated fused silica tube and heated to 1073 K (2 K min−1) for 15 h and slowly cooled to room temperature at a rate of 0.5 K min−1.

Rb12Si17 (90.2 mg; 60 µmol) and cryptand [2.2.2] (127 mg; 337 µmol) were weighed into a Schlenk tube. 2 ml of liquid ammonia were condensed to the reactants, leading to a deep-red solution. The mixture was stirred for 4 h at 195 K, after that time the liquid ammonia was evaporated. The residue was dissolved in 3 ml of anhydrous pyridine and stirred overnight at room temperature. The resulting deep-purple solution was filtered and layered with 4 ml toluene. The title compound crystallized as deep purple/black plates and was isolated after 7 months.

The very air- and moisture-sensitive crystals were transferred from the mother liquor into perfluoropolyalkyl ether oil inside a glove box. Single crystals were fixed on a glass capillary and positioned in a 100 K cold N2 stream.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The highest and lowest remaining electron densities are located at 0.99 Å and at 0.80 Å from the Rb site, respectively.

Structure description top

From the reaction of pyridine with alkali metals, it is known that pyridine undergoes a coupling reaction to 4,4'-bipyridine which leads to the corresponding radical monoanion (Ward, 1961; Schmulbach et al., 1968). Recently, we have investigated the same species after reaction of the Zintl phase K12Si17 with pyridine (Benda & Fässler, 2014). During our recent experiments with pyridine, we found Rb12Si17 also works as a reducing agent, leading to 4,4'-bipyridinidyl radical monoanions. Due to inversion symmetry, the bipyridinidyl molecule in the title compound is planar (Fig. 1). The C—C distances range between 1.368 (3) and 1.431 (3) Å and the C—N distances are 1.353 (3) and 1.354 (3) Å,which agrees well with those of previously reported compounds (Benda & Fässler, 2014; Denning et al., 2008). In the crystal, the molecular entities are arranged in a rock salt type of structure (Figs. 2 and 3).

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. Molecular entities of the title compound. Anisotropic displacement ellipsoids are drawn at the 70% probability level. [Symmetry codes: (i) −x + 3/2, y, −z + 1/2; (ii) −x, −y + 1, −z.]
[Figure 2] Fig. 2. Part of the crystal structure in a view along [100]. Anisotropic displacement ellipsoids are drawn at the 70% probability level, H atoms are omitted for clarity.
[Figure 3] Fig. 3. Distorted rock salt type packing of the entities in the title compound. H atoms and cryptand molecules are omitted for clarity.
(4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane-κ8N2,O6)rubidium 4,4'-bipyridinidyl top
Crystal data top
[Rb(C18H36N2O6)](C10H8N2)F(000) = 650
Mr = 618.14Dx = 1.392 Mg m−3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yacCell parameters from 3923 reflections
a = 11.2326 (4) Åθ = 3.1–31.1°
b = 8.0250 (3) ŵ = 1.73 mm−1
c = 16.3653 (7) ÅT = 100 K
β = 91.950 (3)°Block, violet
V = 1474.34 (10) Å30.25 × 0.20 × 0.15 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer		2895 independent reflections
Radiation source: fine-focus sealed tube2530 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 16 pixels mm-1θmax = 26.0°, θmin = 2.8°
φ– and ω–rotation scansh = −13→13
Absorption correction: multi-scan
(SADABS; Bruker, 2001).		k = −9→7
Tmin = 0.617, Tmax = 0.746l = −20→20
12998 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029All H-atom parameters refined
wR(F2) = 0.065 w = 1/[σ2(Fo2) + (0.0338P)2 + 0.2598P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2895 reflectionsΔρmax = 0.54 e Å−3
265 parametersΔρmin = −0.33 e Å−3
Crystal data top
[Rb(C18H36N2O6)](C10H8N2)V = 1474.34 (10) Å3
Mr = 618.14Z = 2
Monoclinic, P2/nMo Kα radiation
a = 11.2326 (4) ŵ = 1.73 mm−1
b = 8.0250 (3) ÅT = 100 K
c = 16.3653 (7) Å0.25 × 0.20 × 0.15 mm
β = 91.950 (3)°
Data collection top
Bruker APEXII CCD
diffractometer		2895 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001).		2530 reflections with I > 2σ(I)
Tmin = 0.617, Tmax = 0.746Rint = 0.040
12998 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0290 restraints
wR(F2) = 0.065All H-atom parameters refined
S = 1.04Δρmax = 0.54 e Å−3
2895 reflectionsΔρmin = −0.33 e Å−3
265 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Rb0.75000.98082 (3)0.25000.01492 (9)
N10.48347 (14)0.98021 (19)0.21052 (10)0.0173 (4)
O10.65700 (11)1.09295 (17)0.08964 (8)0.0197 (3)
O20.62010 (11)0.66979 (16)0.24532 (8)0.0184 (3)
O30.59695 (11)1.13750 (17)0.36291 (8)0.0191 (3)
C10.45767 (18)1.0318 (3)0.12513 (13)0.0198 (4)
H1A0.4648 (16)0.933 (2)0.0903 (12)0.012 (5)*
H1B0.3742 (19)1.070 (3)0.1178 (13)0.020 (5)*
C20.54038 (18)1.1634 (3)0.09462 (13)0.0190 (4)
H2A0.5114 (16)1.200 (2)0.0410 (14)0.018 (5)*
H2B0.5454 (17)1.260 (3)0.1307 (13)0.018 (5)*
C30.73661 (18)1.1993 (3)0.04795 (13)0.0198 (4)
H3A0.7116 (18)1.210 (3)−0.0112 (14)0.026 (6)*
H3B0.7376 (15)1.309 (2)0.0703 (11)0.007 (5)*
C40.43388 (18)0.8127 (3)0.22370 (14)0.0201 (5)
H4A0.4206 (18)0.798 (3)0.2818 (14)0.023 (6)*
H4B0.3556 (18)0.801 (2)0.1961 (13)0.019 (5)*
C50.51306 (18)0.6740 (3)0.19518 (13)0.0201 (5)
H5A0.4743 (18)0.573 (3)0.1981 (13)0.018 (5)*
H5B0.5364 (17)0.690 (2)0.1353 (14)0.020 (5)*
C60.69328 (18)0.5319 (3)0.22490 (14)0.0203 (4)
H6A0.6518 (18)0.433 (3)0.2362 (13)0.018 (5)*
H6B0.7109 (18)0.532 (2)0.1699 (14)0.020 (6)*
C70.43213 (19)1.1010 (3)0.26717 (13)0.0203 (5)
H7A0.4509 (18)1.213 (3)0.2512 (14)0.028 (6)*
H7B0.3478 (19)1.093 (3)0.2669 (13)0.020 (5)*
C80.47558 (18)1.0854 (3)0.35481 (13)0.0206 (5)
H8A0.4293 (18)1.156 (3)0.3860 (14)0.023 (6)*
H8B0.4711 (17)0.967 (3)0.3760 (13)0.015 (5)*
C90.64053 (19)1.1263 (3)0.44585 (12)0.0196 (5)
H9A0.5880 (17)1.191 (3)0.4829 (13)0.019 (5)*
H9B0.6428 (16)1.008 (2)0.4627 (12)0.013 (5)*
C100.05631 (17)0.4756 (2)0.01722 (12)0.0175 (4)
C110.09578 (19)0.5182 (3)0.09816 (13)0.0224 (5)
H110.0443 (19)0.578 (3)0.1335 (14)0.023 (6)*
C120.2064 (2)0.4722 (3)0.12761 (14)0.0272 (5)
H120.230 (2)0.509 (3)0.1814 (16)0.033 (6)*
N20.28739 (16)0.3822 (2)0.08709 (12)0.0287 (4)
C130.24848 (19)0.3376 (3)0.01101 (14)0.0244 (5)
H130.3029 (18)0.271 (3)−0.0177 (13)0.019 (5)*
C140.14073 (18)0.3783 (3)−0.02572 (13)0.0194 (4)
H140.1230 (17)0.341 (2)−0.0796 (13)0.016 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Rb0.01480 (14)0.01598 (16)0.01421 (14)0.0000.00399 (10)0.000
N10.0178 (8)0.0164 (9)0.0177 (9)−0.0012 (7)0.0017 (7)−0.0001 (7)
O10.0187 (7)0.0181 (8)0.0226 (8)−0.0006 (6)0.0048 (6)0.0061 (6)
O20.0186 (7)0.0166 (8)0.0198 (8)0.0002 (6)0.0006 (6)−0.0025 (6)
O30.0169 (7)0.0275 (8)0.0133 (7)0.0004 (6)0.0042 (6)−0.0010 (6)
C10.0176 (10)0.0222 (12)0.0196 (11)0.0004 (9)−0.0017 (8)−0.0010 (9)
C20.0194 (11)0.0197 (12)0.0178 (11)0.0022 (9)−0.0004 (9)0.0020 (9)
C30.0255 (11)0.0168 (12)0.0174 (11)−0.0039 (9)0.0024 (9)0.0030 (9)
C40.0166 (11)0.0222 (12)0.0219 (12)−0.0027 (9)0.0035 (9)0.0017 (9)
C50.0196 (11)0.0187 (12)0.0220 (12)−0.0038 (9)0.0012 (9)−0.0012 (9)
C60.0239 (11)0.0131 (11)0.0242 (12)−0.0005 (9)0.0056 (9)−0.0017 (9)
C70.0138 (11)0.0197 (12)0.0279 (12)0.0019 (9)0.0051 (9)−0.0026 (9)
C80.0179 (11)0.0227 (12)0.0219 (12)0.0011 (9)0.0087 (9)−0.0040 (9)
C90.0274 (12)0.0187 (12)0.0131 (10)0.0048 (9)0.0054 (9)−0.0013 (8)
C100.0218 (10)0.0133 (10)0.0175 (10)−0.0023 (8)0.0038 (8)0.0030 (8)
C110.0291 (11)0.0203 (12)0.0178 (10)−0.0007 (10)0.0028 (9)−0.0004 (9)
C120.0323 (12)0.0294 (13)0.0196 (11)−0.0032 (10)−0.0052 (10)0.0007 (9)
N20.0248 (10)0.0325 (12)0.0286 (11)0.0019 (8)−0.0004 (8)0.0055 (8)
C130.0222 (12)0.0222 (12)0.0293 (13)0.0021 (9)0.0090 (10)0.0044 (9)
C140.0240 (11)0.0170 (11)0.0175 (11)−0.0014 (9)0.0052 (9)0.0003 (8)
Geometric parameters (Å, º) top
Rb—O32.8578 (13)C4—H4A0.97 (2)
Rb—O3i2.8578 (14)C4—H4B0.979 (19)
Rb—O22.8909 (13)C5—H5A0.93 (2)
Rb—O2i2.8909 (13)C5—H5B1.03 (2)
Rb—O1i2.9329 (13)C6—C6i1.492 (4)
Rb—O12.9329 (13)C6—H6A0.94 (2)
Rb—N1i3.0411 (16)C6—H6B0.93 (2)
Rb—N13.0412 (16)C7—C81.504 (3)
N1—C71.472 (3)C7—H7A0.96 (2)
N1—C41.474 (3)C7—H7B0.95 (2)
N1—C11.477 (3)C8—H8A0.93 (2)
O1—C31.426 (2)C8—H8B1.02 (2)
O1—C21.432 (2)C9—H9A1.00 (2)
O2—C61.425 (2)C9—H9B0.991 (19)
O2—C51.433 (2)C10—C10ii1.422 (4)
O3—C81.428 (2)C10—C111.424 (3)
O3—C91.430 (2)C10—C141.431 (3)
C1—C21.503 (3)C11—C121.368 (3)
C1—H1A0.98 (2)C11—H110.96 (2)
C1—H1B0.99 (2)C12—N21.353 (3)
C2—H2A0.97 (2)C12—H120.96 (2)
C2—H2B0.97 (2)N2—C131.354 (3)
C3—C9i1.499 (3)C13—C141.372 (3)
C3—H3A1.00 (2)C13—H130.95 (2)
C3—H3B0.956 (19)C14—H140.95 (2)
C4—C51.509 (3)
O3—Rb—O3i127.80 (6)C9i—C3—H3A109.0 (12)
O3—Rb—O294.75 (4)O1—C3—H3B111.7 (11)
O3i—Rb—O2132.60 (4)C9i—C3—H3B109.6 (10)
O3—Rb—O2i132.60 (4)H3A—C3—H3B106.7 (16)
O3i—Rb—O2i94.75 (4)N1—C4—C5113.45 (17)
O2—Rb—O2i60.60 (5)N1—C4—H4A108.7 (13)
O3—Rb—O1i59.35 (4)C5—C4—H4A109.1 (13)
O3i—Rb—O1i103.87 (4)N1—C4—H4B110.7 (12)
O2—Rb—O1i116.92 (4)C5—C4—H4B108.6 (12)
O2i—Rb—O1i94.42 (4)H4A—C4—H4B106.0 (17)
O3—Rb—O1103.87 (4)O2—C5—C4109.39 (16)
O3i—Rb—O159.35 (4)O2—C5—H5A109.7 (12)
O2—Rb—O194.42 (4)C4—C5—H5A110.5 (13)
O2i—Rb—O1116.92 (4)O2—C5—H5B108.2 (11)
O1i—Rb—O1144.27 (5)C4—C5—H5B112.1 (11)
O3—Rb—N1i118.22 (4)H5A—C5—H5B107.0 (17)
O3i—Rb—N1i61.87 (4)O2—C6—C6i111.06 (15)
O2—Rb—N1i119.77 (4)O2—C6—H6A108.3 (13)
O2i—Rb—N1i60.04 (4)C6i—C6—H6A108.1 (12)
O1i—Rb—N1i59.49 (4)O2—C6—H6B111.5 (13)
O1—Rb—N1i120.57 (4)C6i—C6—H6B109.1 (13)
O3—Rb—N161.87 (4)H6A—C6—H6B108.6 (18)
O3i—Rb—N1118.22 (4)N1—C7—C8115.09 (17)
O2—Rb—N160.04 (4)N1—C7—H7A110.5 (14)
O2i—Rb—N1119.77 (4)C8—C7—H7A105.7 (13)
O1i—Rb—N1120.58 (4)N1—C7—H7B111.5 (13)
O1—Rb—N159.49 (4)C8—C7—H7B106.9 (13)
N1i—Rb—N1179.82 (6)H7A—C7—H7B106.7 (18)
C7—N1—C4110.51 (17)O3—C8—C7109.98 (18)
C7—N1—C1110.05 (16)O3—C8—H8A108.7 (13)
C4—N1—C1109.33 (15)C7—C8—H8A107.6 (13)
C7—N1—Rb105.61 (11)O3—C8—H8B107.5 (11)
C4—N1—Rb110.15 (11)C7—C8—H8B112.7 (11)
C1—N1—Rb111.14 (11)H8A—C8—H8B110.3 (19)
C3—O1—C2112.38 (15)O3—C9—C3i108.93 (17)
C3—O1—Rb113.67 (11)O3—C9—H9A110.6 (11)
C2—O1—Rb111.65 (11)C3i—C9—H9A108.5 (11)
C6—O2—C5111.30 (15)O3—C9—H9B109.2 (12)
C6—O2—Rb112.47 (11)C3i—C9—H9B109.9 (11)
C5—O2—Rb114.08 (11)H9A—C9—H9B109.7 (17)
C8—O3—C9111.38 (16)C10ii—C10—C11123.2 (2)
C8—O3—Rb113.86 (11)C10ii—C10—C14123.4 (2)
C9—O3—Rb113.09 (11)C11—C10—C14113.41 (18)
N1—C1—C2114.05 (16)C12—C11—C10120.9 (2)
N1—C1—H1A107.8 (11)C12—C11—H11118.7 (12)
C2—C1—H1A108.1 (12)C10—C11—H11120.4 (12)
N1—C1—H1B110.9 (12)N2—C12—C11126.1 (2)
C2—C1—H1B109.4 (12)N2—C12—H12116.3 (14)
H1A—C1—H1B106.2 (16)C11—C12—H12117.5 (14)
O1—C2—C1108.57 (17)C12—N2—C13113.00 (18)
O1—C2—H2A110.3 (12)N2—C13—C14126.3 (2)
C1—C2—H2A108.7 (12)N2—C13—H13114.3 (12)
O1—C2—H2B108.3 (11)C14—C13—H13119.4 (12)
C1—C2—H2B112.3 (13)C13—C14—C10120.3 (2)
H2A—C2—H2B108.6 (17)C13—C14—H14119.1 (12)
O1—C3—C9i108.96 (17)C10—C14—H14120.6 (12)
O1—C3—H3A110.8 (12)
Symmetry codes: (i) −x+3/2, y, −z+1/2; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula[Rb(C18H36N2O6)](C10H8N2)
Mr618.14
Crystal system, space groupMonoclinic, P2/n
Temperature (K)100
a, b, c (Å)11.2326 (4), 8.0250 (3), 16.3653 (7)
β (°) 91.950 (3)
V (Å3)1474.34 (10)
Z2
Radiation typeMo Kα
µ (mm−1)1.73
Crystal size (mm)0.25 × 0.20 × 0.15
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2001).
Tmin, Tmax0.617, 0.746
No. of measured, independent and
observed [I > 2σ(I)] reflections		12998, 2895, 2530
Rint0.040
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.065, 1.04
No. of reflections2895
No. of parameters265
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.54, −0.33

Computer programs: APEX2 (Bruker, 2012), SAINT (Bruker, 2012), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), DIAMOND (Brandenburg & Putz, 2012).

 

Acknowledgements

This work was supported by the Deutsche Forschungsgemeinschaft (DFG) through the TUM Inter­national Graduate School of Science and Engineering (IGSSE) and the Technische Universität München within the funding programme Open Access Publishing.

References

First citationBenda, C. & Fässler, T. F. (2014). Z. Naturforsch. Teil B, 69, 1119–1123.  CAS Google Scholar
 First citationBrandenburg, K. & Putz, H. (2012). DIAMOND . Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2012). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDenning, M. S., Irwin, M. & Goicoechea, J. M. (2008). Inorg. Chem. 47, 6118–6120.  Web of Science CSD CrossRef PubMed CAS Google Scholar
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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationWard, R. L. (1961). J. Am. Chem. Soc. 83, 3623–3626.  CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 3| March 2016| x160505
doi:10.1107/S2414314616005058
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