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ISSN: 2056-9890

1-Benzyl-2-di­methyl­amino-3-methyl-3,4,5,6-tetra­hydro­pyrimidin-1-ium bromide

aInstitut für Organische Chemie, Universität Stuttgart, Pfaffenwaldring 55, 70569 Stuttgart, Germany, and bFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@htw-aalen.de

(Received 13 June 2012; accepted 27 June 2012; online 4 July 2012)

In the title molecular salt, C14H22N3+·Br, the ring incorporating the guanidinium grouping exhibits a half-chair conformation and the dihedral angle between the N—C—N and C—C—C planes is 55.0 (3)°. The C—N bond lengths in the central CN3 unit are 1.333 (4), 1.338 (3) and 1.341 (4) Å, indicating partial double-bond character. The central C atom is bonded to the three N atoms in a nearly ideal trigonal–planar geometry and the positive charge is delocalized in the CN3 plane. The distances between the N atom and the terminal methyl C atoms [1.453 (4)–1.461 (4) Å] are all close to a typical single C—N bond length.

Related literature

For the crystal structure of N,N,N′,N′- tetra­methyl­chloro­formamidinium chloride, see: Tiritiris & Kantlehner (2008[Tiritiris, I. & Kantlehner, W. (2008). Z. Kristallogr. 223, 345-346.]). For the synthesis of 1-methyl-2-dimethyl­amino-1,4,5,6-tetra­hydro­pyrimidine and derived guanidinium salts, see: Tiritiris & Kantlehner (2012b[Tiritiris, I. & Kantlehner, W. (2012b). Z. Naturforsch. Teil B. In the press.]). For the structure of 2-dimethyl­amino-1-(2-eth­oxy-2-oxoeth­yl)-3-methyl-3,4,5,6-tetra­hydro­pyri­midin-1-ium tetra­phenyl­borate see: Tiritiris & Kantlehner (2012a[Tiritiris, I. & Kantlehner, W. (2012a). Acta Cryst. E68, o2002.]).

[Scheme 1]

Experimental

Crystal data
  • C14H22N3+·Br

  • Mr = 312.25

  • Monoclinic, P 21 /n

  • a = 10.7814 (7) Å

  • b = 11.8538 (8) Å

  • c = 11.4782 (8) Å

  • β = 93.332 (8)°

  • V = 1464.44 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.80 mm−1

  • T = 293 K

  • 0.24 × 0.17 × 0.13 mm

Data collection
  • Bruker–Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.552, Tmax = 0.695

  • 14052 measured reflections

  • 3536 independent reflections

  • 1812 reflections with I > 2σ(I)

  • Rint = 0.064

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.089

  • S = 0.81

  • 3536 reflections

  • 166 parameters

  • H-atom parameters constrained

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.49 e Å−3

Data collection: COLLECT (Hooft, 2004[Hooft, R. W. W. (2004). COLLECT. Bruker-Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, part A, edited by C. W. Carter & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Putz, 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Since we have established a simple method for synthesizing the cyclic guanidine 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine (Tiritiris & Kantlehner, 2013) from N,N,N',N'-tetramethylchloroformamidinium chloride (Tiritiris & Kantlehner, 2008) and N-methyl-propane-1,3-diamine, the synthesis and characterization of related ionic tetrahydropyrimidinium derivatives, which are potentially pharmacologically active, was an aim of our investigations. The reaction of the free guanidine base with ethyl bromoacetate has been recently described by us and the resulting bromide was converted by anion exchange to the tetraphenylborate salt giving single crystals suitable for X-ray structure analysis (Tiritiris & Kantlehner, 2012). By alkylation of the free nitrogen position of the molecule with alkyl halides, it is possible to obtain guanidinium salts with a different substitution pattern, which one representative is the here presented title compound. According to the structure analysis, isolated guanidinium ions and bromide ions are present and no specific interactions between them have been observed. Prominent bond parameters in the guanidinium ion are: C1–N1 = 1.333 (4) Å, C1–N2 = 1.341 (4) Å and C1–N3 = 1.338 (3) Å. The N–C1–N angles are: 121.2 (3)° (N1–C1–N2), 119.8 (3)° (N2–C1–N3) and 118.9 (3)° (N1–C1–N3), which indicates a nearly ideal trigonal-planar surrounding of the carbon centre by the nitrogen atoms. The positive charge is completely delocalized on the CN3 plane. The bonds between the N atoms and the terminal C-methyl groups, all have values close to a typical single bond (1.453 (4)–1.461 (4) Å). All remaining C–N distances are between 1.464 (4) and 1.476 (3) Å. The six membered heterocycle exhibits a half-chair conformation (Fig. 1). The carbon atom C6 is not in the ring plane, the angle between the planes N3/C1/N1 and C5/C6/C7 is 55.0 (3)°. This value is slightly larger compared with that one determined for the guanidinium ion in 2-dimethylamino-1- (2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate (Tiritiris & Kantlehner, 2012). The dihedral angle between the planes C1/N1/C7 and C10/C9/C14 is 66.5 (3)°, which shows a significant twisting of the phenyl ring relative to the tetrahydropyrimidine ring.

Related literature top

For the crystal structure of N,N,N',N'- tetramethylchloroformamidinium chloride, see: Tiritiris & Kantlehner (2008). For the synthesis of 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine and derived guanidinium salts, see: Tiritiris & Kantlehner (2013). For the crystal structure of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate see: Tiritiris & Kantlehner (2012).

Experimental top

The title compound has been obtained by reacting equimolar amounts of 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine and benzyl bromide in acetonitrile at room temperature for two hours. After evaporation of the solvent the crude 2-dimethylamino-1-benzyl-3-methyl-3,4,5,6- tetrahydropyrimidin-1-ium bromide was washed with diethylether and dried in vacuo. Single crystals have been obtained by recrystallization from a saturated acetonitrile solution.

Refinement top

The hydrogen atoms of the methyl groups were allowed to rotate with a fixed angle around the C–N bond to best fit the experimental electron density, with U(H) set to 1.5 Ueq(C) and d(C—H) = 0.96 Å. The remaining H atoms were placed in calculated positions with d(C—H) = 0.97 Å (H atoms in CH2 groups) and (C—H) = 0.93 Å (H atoms in the aromatic ring). They were included in the refinement in the riding model approximation, with U(H) set to 1.2 Ueq(C).

Structure description top

Since we have established a simple method for synthesizing the cyclic guanidine 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine (Tiritiris & Kantlehner, 2013) from N,N,N',N'-tetramethylchloroformamidinium chloride (Tiritiris & Kantlehner, 2008) and N-methyl-propane-1,3-diamine, the synthesis and characterization of related ionic tetrahydropyrimidinium derivatives, which are potentially pharmacologically active, was an aim of our investigations. The reaction of the free guanidine base with ethyl bromoacetate has been recently described by us and the resulting bromide was converted by anion exchange to the tetraphenylborate salt giving single crystals suitable for X-ray structure analysis (Tiritiris & Kantlehner, 2012). By alkylation of the free nitrogen position of the molecule with alkyl halides, it is possible to obtain guanidinium salts with a different substitution pattern, which one representative is the here presented title compound. According to the structure analysis, isolated guanidinium ions and bromide ions are present and no specific interactions between them have been observed. Prominent bond parameters in the guanidinium ion are: C1–N1 = 1.333 (4) Å, C1–N2 = 1.341 (4) Å and C1–N3 = 1.338 (3) Å. The N–C1–N angles are: 121.2 (3)° (N1–C1–N2), 119.8 (3)° (N2–C1–N3) and 118.9 (3)° (N1–C1–N3), which indicates a nearly ideal trigonal-planar surrounding of the carbon centre by the nitrogen atoms. The positive charge is completely delocalized on the CN3 plane. The bonds between the N atoms and the terminal C-methyl groups, all have values close to a typical single bond (1.453 (4)–1.461 (4) Å). All remaining C–N distances are between 1.464 (4) and 1.476 (3) Å. The six membered heterocycle exhibits a half-chair conformation (Fig. 1). The carbon atom C6 is not in the ring plane, the angle between the planes N3/C1/N1 and C5/C6/C7 is 55.0 (3)°. This value is slightly larger compared with that one determined for the guanidinium ion in 2-dimethylamino-1- (2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate (Tiritiris & Kantlehner, 2012). The dihedral angle between the planes C1/N1/C7 and C10/C9/C14 is 66.5 (3)°, which shows a significant twisting of the phenyl ring relative to the tetrahydropyrimidine ring.

For the crystal structure of N,N,N',N'- tetramethylchloroformamidinium chloride, see: Tiritiris & Kantlehner (2008). For the synthesis of 1-methyl-2-dimethylamino-1,4,5,6-tetrahydropyrimidine and derived guanidinium salts, see: Tiritiris & Kantlehner (2013). For the crystal structure of 2-dimethylamino-1-(2-ethoxy-2-oxoethyl)-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium tetraphenylborate see: Tiritiris & Kantlehner (2012).

Computing details top

Data collection: COLLECT (Hooft, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with atom labels and 50% probability displacement ellipsoids. All hydrogen atoms were omitted for clarity.
1-Benzyl-2-dimethylamino-3-methyl-3,4,5,6-tetrahydropyrimidin-1-ium bromide top
Crystal data top
C14H22N3+·BrF(000) = 648
Mr = 312.25Dx = 1.416 Mg m3
Monoclinic, P21/nMelting point: 402 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 10.7814 (7) ÅCell parameters from 3536 reflections
b = 11.8538 (8) Åθ = 2.5–28.1°
c = 11.4782 (8) ŵ = 2.80 mm1
β = 93.332 (8)°T = 293 K
V = 1464.44 (17) Å3Block, colorless
Z = 40.24 × 0.17 × 0.13 mm
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3536 independent reflections
Radiation source: sealed tube1812 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.064
φ scans, and ω scansθmax = 28.1°, θmin = 2.5°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1414
Tmin = 0.552, Tmax = 0.695k = 1515
14052 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: difference Fourier map
wR(F2) = 0.089H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0441P)2]
where P = (Fo2 + 2Fc2)/3
3536 reflections(Δ/σ)max < 0.001
166 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C14H22N3+·BrV = 1464.44 (17) Å3
Mr = 312.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.7814 (7) ŵ = 2.80 mm1
b = 11.8538 (8) ÅT = 293 K
c = 11.4782 (8) Å0.24 × 0.17 × 0.13 mm
β = 93.332 (8)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3536 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
1812 reflections with I > 2σ(I)
Tmin = 0.552, Tmax = 0.695Rint = 0.064
14052 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.089H-atom parameters constrained
S = 0.81Δρmax = 0.34 e Å3
3536 reflectionsΔρmin = 0.49 e Å3
166 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.

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) top
xyzUiso*/Ueq
Br10.19725 (3)0.75077 (3)0.59957 (2)0.05182 (11)
N10.1492 (2)0.20807 (19)0.58797 (18)0.0347 (5)
N20.3599 (2)0.2078 (2)0.5530 (2)0.0391 (6)
N30.2549 (2)0.37602 (18)0.57696 (19)0.0354 (5)
C10.2552 (3)0.2632 (2)0.5746 (2)0.0318 (6)
C20.3930 (4)0.1018 (3)0.6102 (3)0.0572 (10)
H2A0.34350.09140.67620.086*
H2B0.47940.10300.63590.086*
H2C0.37810.04070.55620.086*
C30.4411 (3)0.2456 (3)0.4638 (3)0.0568 (8)
H3A0.40460.30980.42390.085*
H3B0.45170.18580.40900.085*
H3C0.52050.26630.49980.085*
C40.3625 (3)0.4382 (3)0.6263 (3)0.0514 (9)
H4A0.41870.38690.66680.077*
H4B0.33560.49410.67990.077*
H4C0.40390.47450.56470.077*
C50.1329 (3)0.4295 (2)0.5823 (3)0.0454 (8)
H5A0.08360.41670.51010.054*
H5B0.14240.51020.59370.054*
C60.0696 (3)0.3774 (3)0.6841 (3)0.0459 (8)
H6A0.12110.38660.75560.055*
H6B0.00960.41410.69380.055*
C70.0500 (3)0.2536 (3)0.6579 (2)0.0431 (6)
H7A0.04850.21200.73060.052*
H7B0.02970.24330.61560.052*
C80.1207 (3)0.0990 (2)0.5305 (3)0.0468 (8)
H8A0.03200.08570.53040.056*
H8B0.16200.03930.57570.056*
C90.1602 (3)0.0927 (2)0.4063 (2)0.0379 (7)
C100.2077 (3)0.0062 (2)0.3643 (3)0.0461 (8)
H100.21870.06810.41360.055*
C110.2395 (4)0.0142 (3)0.2485 (3)0.0548 (9)
H110.26960.08180.22030.066*
C120.2262 (3)0.0771 (3)0.1770 (3)0.0499 (8)
H120.25000.07250.10050.060*
C130.1780 (3)0.1759 (3)0.2172 (2)0.0476 (8)
H130.16870.23780.16770.057*
C140.1432 (3)0.1838 (3)0.3311 (2)0.0438 (7)
H140.10840.25020.35730.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0600 (2)0.05218 (17)0.04289 (15)0.00288 (19)0.00030 (12)0.00128 (17)
N10.0360 (15)0.0377 (11)0.0313 (11)0.0062 (10)0.0099 (10)0.0045 (9)
N20.0390 (16)0.0448 (12)0.0343 (12)0.0072 (11)0.0088 (10)0.0030 (10)
N30.0341 (14)0.0334 (11)0.0388 (12)0.0005 (11)0.0021 (10)0.0032 (10)
C10.0370 (16)0.0352 (14)0.0235 (10)0.0006 (14)0.0039 (10)0.0005 (12)
C20.070 (3)0.0494 (19)0.0523 (19)0.0201 (18)0.0041 (17)0.0071 (15)
C30.0417 (18)0.084 (2)0.0465 (15)0.001 (2)0.0164 (13)0.005 (2)
C40.050 (2)0.0432 (18)0.060 (2)0.0141 (15)0.0044 (16)0.0041 (15)
C50.049 (2)0.0398 (16)0.0476 (17)0.0102 (14)0.0023 (15)0.0022 (13)
C60.040 (2)0.0494 (17)0.0488 (17)0.0084 (14)0.0080 (14)0.0109 (14)
C70.0351 (15)0.0513 (15)0.0440 (13)0.0046 (18)0.0115 (11)0.0070 (17)
C80.060 (2)0.0419 (16)0.0397 (16)0.0175 (15)0.0171 (15)0.0114 (13)
C90.0402 (19)0.0373 (14)0.0369 (14)0.0109 (13)0.0086 (12)0.0076 (12)
C100.059 (2)0.0329 (14)0.0465 (17)0.0021 (14)0.0074 (15)0.0029 (12)
C110.068 (3)0.047 (2)0.0509 (17)0.0033 (17)0.0159 (16)0.0164 (16)
C120.052 (2)0.064 (2)0.0343 (15)0.0064 (17)0.0079 (14)0.0130 (15)
C130.054 (2)0.0525 (19)0.0350 (15)0.0053 (16)0.0051 (14)0.0023 (13)
C140.049 (2)0.0402 (17)0.0417 (16)0.0005 (14)0.0004 (14)0.0076 (13)
Geometric parameters (Å, º) top
N1—C11.333 (4)C5—H5B0.9700
N1—C81.476 (3)C6—C71.511 (4)
N1—C71.476 (3)C6—H6A0.9700
N2—C11.341 (4)C6—H6B0.9700
N2—C21.453 (4)C7—H7A0.9700
N2—C31.456 (4)C7—H7B0.9700
N3—C11.338 (3)C8—C91.513 (4)
N3—C41.461 (4)C8—H8A0.9700
N3—C51.464 (4)C8—H8B0.9700
C2—H2A0.9600C9—C101.377 (4)
C2—H2B0.9600C9—C141.387 (4)
C2—H2C0.9600C10—C111.395 (4)
C3—H3A0.9600C10—H100.9300
C3—H3B0.9600C11—C121.361 (4)
C3—H3C0.9600C11—H110.9300
C4—H4A0.9600C12—C131.372 (4)
C4—H4B0.9600C12—H120.9300
C4—H4C0.9600C13—C141.385 (4)
C5—C61.518 (4)C13—H130.9300
C5—H5A0.9700C14—H140.9300
C1—N1—C8122.4 (2)C7—C6—C5107.8 (2)
C1—N1—C7122.5 (2)C7—C6—H6A110.1
C8—N1—C7115.1 (2)C5—C6—H6A110.1
C1—N2—C2121.8 (3)C7—C6—H6B110.1
C1—N2—C3121.7 (2)C5—C6—H6B110.1
C2—N2—C3116.3 (3)H6A—C6—H6B108.5
C1—N3—C4120.6 (3)N1—C7—C6111.4 (2)
C1—N3—C5115.9 (2)N1—C7—H7A109.3
C4—N3—C5117.4 (2)C6—C7—H7A109.3
N1—C1—N3118.9 (3)N1—C7—H7B109.3
N1—C1—N2121.2 (3)C6—C7—H7B109.3
N3—C1—N2119.8 (3)H7A—C7—H7B108.0
N2—C2—H2A109.5N1—C8—C9113.7 (2)
N2—C2—H2B109.5N1—C8—H8A108.8
H2A—C2—H2B109.5C9—C8—H8A108.8
N2—C2—H2C109.5N1—C8—H8B108.8
H2A—C2—H2C109.5C9—C8—H8B108.8
H2B—C2—H2C109.5H8A—C8—H8B107.7
N2—C3—H3A109.5C10—C9—C14118.9 (3)
N2—C3—H3B109.5C10—C9—C8120.1 (3)
H3A—C3—H3B109.5C14—C9—C8120.9 (3)
N2—C3—H3C109.5C9—C10—C11120.6 (3)
H3A—C3—H3C109.5C9—C10—H10119.7
H3B—C3—H3C109.5C11—C10—H10119.7
N3—C4—H4A109.5C12—C11—C10119.9 (3)
N3—C4—H4B109.5C12—C11—H11120.1
H4A—C4—H4B109.5C10—C11—H11120.1
N3—C4—H4C109.5C11—C12—C13120.3 (3)
H4A—C4—H4C109.5C11—C12—H12119.9
H4B—C4—H4C109.5C13—C12—H12119.9
N3—C5—C6107.6 (2)C12—C13—C14120.3 (3)
N3—C5—H5A110.2C12—C13—H13119.9
C6—C5—H5A110.2C14—C13—H13119.9
N3—C5—H5B110.2C13—C14—C9120.1 (3)
C6—C5—H5B110.2C13—C14—H14120.0
H5A—C5—H5B108.5C9—C14—H14120.0
C8—N1—C1—N3147.7 (3)C1—N1—C7—C614.4 (4)
C7—N1—C1—N330.0 (4)C8—N1—C7—C6163.5 (3)
C8—N1—C1—N228.8 (4)C5—C6—C7—N131.7 (3)
C7—N1—C1—N2153.4 (3)C1—N1—C8—C940.3 (4)
C4—N3—C1—N1145.8 (3)C7—N1—C8—C9137.6 (3)
C5—N3—C1—N16.1 (3)N1—C8—C9—C10142.5 (3)
C4—N3—C1—N237.6 (4)N1—C8—C9—C1441.0 (4)
C5—N3—C1—N2170.5 (2)C14—C9—C10—C110.7 (5)
C2—N2—C1—N139.7 (4)C8—C9—C10—C11177.3 (3)
C3—N2—C1—N1135.0 (3)C9—C10—C11—C121.6 (5)
C2—N2—C1—N3143.8 (3)C10—C11—C12—C132.1 (5)
C3—N2—C1—N341.6 (4)C11—C12—C13—C140.4 (5)
C1—N3—C5—C652.6 (3)C12—C13—C14—C91.8 (5)
C4—N3—C5—C6100.2 (3)C10—C9—C14—C132.4 (5)
N3—C5—C6—C763.5 (3)C8—C9—C14—C13178.9 (3)

Experimental details

Crystal data
Chemical formulaC14H22N3+·Br
Mr312.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)10.7814 (7), 11.8538 (8), 11.4782 (8)
β (°) 93.332 (8)
V3)1464.44 (17)
Z4
Radiation typeMo Kα
µ (mm1)2.80
Crystal size (mm)0.24 × 0.17 × 0.13
Data collection
DiffractometerBruker–Nonius KappaCCD
Absorption correctionMulti-scan
(Blessing, 1995)
Tmin, Tmax0.552, 0.695
No. of measured, independent and
observed [I > 2σ(I)] reflections
14052, 3536, 1812
Rint0.064
(sin θ/λ)max1)0.662
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.089, 0.81
No. of reflections3536
No. of parameters166
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.49

Computer programs: COLLECT (Hooft, 2004), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

 

Acknowledgements

The authors thank Dr F. Lissner (Institut für Anorganische Chemie, Universität Stuttgart) for the data collection.

References

First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBrandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationHooft, R. W. W. (2004). COLLECT. Bruker–Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, part A, edited by C. W. Carter & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTiritiris, I. & Kantlehner, W. (2008). Z. Kristallogr. 223, 345–346.  CAS Google Scholar
First citationTiritiris, I. & Kantlehner, W. (2012a). Acta Cryst. E68, o2002.  CSD CrossRef IUCr Journals Google Scholar
First citationTiritiris, I. & Kantlehner, W. (2012b). Z. Naturforsch. Teil B. In the press.  Google Scholar

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