organic compounds
of dicyclohexylammonium nitrate(V)
aDepartment of Chemistry, Wrocław University of Technology, 27 Wybrzeże Wyspiańskiego St., 50-370 Wrocław, Poland
*Correspondence e-mail: ewa.matczak-jon@pwr.edu.pl
In the title molecular salt, C12H24N+·NO3−, the cyclohexyl rings adopt chair conformations with the exocyclic C—N bonds in equatorial orientations. In the crystal, a bifurcated N—H⋯(O,O) hydrogen bond links the cation to the anion; the ion pairs are linked via C—H⋯O hydrogen bonds, forming layers in the ac plane.
CCDC reference: 1431025
1. Related literature
For the et al. (1999). For other crystal structures of dicyclohexylammonium salts, see: Ng (1995); Bi et al. (2002); Lo & Ng (2008); Khawar Rauf et al. (2008); Selvakumaran et al. (2011); Ndoye et al. (2014). For crystal structures of carboxylate salts with the dicyclohexylammonium cation belonging to the low molecular weight gelators (LMWGs) class of compounds and exhibiting gelling properties, see: Trivedi et al. (2004, 2005); Sahoo & Dastidar (2012); Rojek et al. (2015).
of dicyclohexylammonium nitrate(III), see: Golobič2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: CrysAlis PRO (Agilent, 2011); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 1431025
https://doi.org/10.1107/S2056989015019386/su5222sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015019386/su5222Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989015019386/su5222Isup3.txt
Supporting information file. DOI: https://doi.org/10.1107/S2056989015019386/su5222Isup4.cml
The dicyclohexylammonium cation has been widely used in the preparation of crystalline salts like chloride (Ng, 1995), nitrate(III) (Golobič et al., 1999), tungstate (Bi et al., 2002), bromide (Lo & Ng, 2008), thiocyanate (Khawar Rauf et al., 2008; Selvakumaran et al., 2011) or sulfate(VI) (Ndoye et al., 2014) salts. In recent years, there has been increased interest in dicyclohexylammonium carboxylate salts due to their potential applications as materials capable of immobilizing organic solvents to form gels, known as low molecular weight gelators - LMWGs (Trivedi et al., 2004, 2005; Sahoo & Dastidar, 2012; Rojek et al., 2015).
The title molecular salt, Fig. 1, consists of an
comprising a dicyclohexylammonium cation connected to a nitrate(V) anion by N1—H1N···O3 and N1—H1N···O2 hydrogen bonds (Table 1). Additionally, the is stabilized by a C22—H22B···O2 interaction (Fig. 1 and Table 1). The N2—O2 and N2—O3 bond lengths of the nitrate(V) anion are almost equal [1.258 (2) and 1.255 (2) Å, respectively] and longer than the N2—O1 bond length [1.2353 (18) Å]. The C11—N1—C12 angle in the dicyclohexylammonium cation [117.34 (12)°] is larger than expected for a tetrahedral N atom. This is attributed to the imposed by the cyclohexane rings, each of which adopt a chair conformation. The N1—C11 and N1—C12 bond lengths [1.5077 (19) and 1.510 (2) Å, respectively] are similar to those observed for other dicyclohexylammonium salts (Golobič et al., 1999).In the crystal, the N1—H2N···O2i hydrogen bonds combine ion pairs into infinite chains parallel to the c axis. The chains are additionally stabilized by C12—H12···O3iii contacts and further packed in a parallel fashion by means of C62—H62A···O1ii and C11—H11···O1ii (symmetry codes as in Table 1) interactions giving rise to layers in the ac plane (Fig. 2).
Dicyclohexylamine (1 mmol, 201 ml) was added to methanol (4 ml) under vigorous stirring. The clear solution was combined with nitric(V) acid (1 M, 1 ml) and stirred for 20 min. The resulting solution was left to crystallize at room temperature. After one week, large block-shaped colourless single crystals of the title salt suitable for X-ray
were obtained.The dicyclohexylammonium cation has been widely used in the preparation of crystalline salts like chloride (Ng, 1995), nitrate(III) (Golobič et al., 1999), tungstate (Bi et al., 2002), bromide (Lo & Ng, 2008), thiocyanate (Khawar Rauf et al., 2008; Selvakumaran et al., 2011) or sulfate(VI) (Ndoye et al., 2014) salts. In recent years, there has been increased interest in dicyclohexylammonium carboxylate salts due to their potential applications as materials capable of immobilizing organic solvents to form gels, known as low molecular weight gelators - LMWGs (Trivedi et al., 2004, 2005; Sahoo & Dastidar, 2012; Rojek et al., 2015).
The title molecular salt, Fig. 1, consists of an
comprising a dicyclohexylammonium cation connected to a nitrate(V) anion by N1—H1N···O3 and N1—H1N···O2 hydrogen bonds (Table 1). Additionally, the is stabilized by a C22—H22B···O2 interaction (Fig. 1 and Table 1). The N2—O2 and N2—O3 bond lengths of the nitrate(V) anion are almost equal [1.258 (2) and 1.255 (2) Å, respectively] and longer than the N2—O1 bond length [1.2353 (18) Å]. The C11—N1—C12 angle in the dicyclohexylammonium cation [117.34 (12)°] is larger than expected for a tetrahedral N atom. This is attributed to the imposed by the cyclohexane rings, each of which adopt a chair conformation. The N1—C11 and N1—C12 bond lengths [1.5077 (19) and 1.510 (2) Å, respectively] are similar to those observed for other dicyclohexylammonium salts (Golobič et al., 1999).In the crystal, the N1—H2N···O2i hydrogen bonds combine ion pairs into infinite chains parallel to the c axis. The chains are additionally stabilized by C12—H12···O3iii contacts and further packed in a parallel fashion by means of C62—H62A···O1ii and C11—H11···O1ii (symmetry codes as in Table 1) interactions giving rise to layers in the ac plane (Fig. 2).
For the
of dicyclohexylammonium nitrate(III), see: Golobič et al. (1999). For other crystal structures of dicyclohexylammonium salts, see: Ng (1995); Bi et al. (2002); Lo & Ng (2008); Khawar Rauf et al. (2008); Selvakumaran et al. (2011); Ndoye et al. (2014). For crystal structures of carboxylate salts with the dicyclohexylammonium cation belonging to the low molecular weight gelators (LMWGs) class of compounds and exhibiting gelling properties, see: Trivedi et al. (2004, 2005); Sahoo & Dastidar (2012); Rojek et al. (2015).Dicyclohexylamine (1 mmol, 201 ml) was added to methanol (4 ml) under vigorous stirring. The clear solution was combined with nitric(V) acid (1 M, 1 ml) and stirred for 20 min. The resulting solution was left to crystallize at room temperature. After one week, large block-shaped colourless single crystals of the title salt suitable for X-ray
were obtained. detailsThe N-bound H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model; C—H = 0.99 Å with Uiso(H) = 1.2Ueq(C).
Data collection: CrysAlis PRO (Agilent, 2011); cell
CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The asymmetric unit of the title molecular salt, showing the atom-numbering scheme and the symmetry-independent hydrogen bonds (orange and light-blue dashed lines; see Table 1). Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. A view along the b axis of the crystal packing of the title molecular salt, showing the hydrogen-bonded chains assembled into a layer in the ac plane. Hydrogen bonds are drawn as yellow and light-blue dashed lines (see Table 1). H atoms on C atoms of the cyclohexane rings not involved in hydrogen bonds have been omitted for clarity. |
C12H24N+·NO3− | F(000) = 536 |
Mr = 244.33 | Dx = 1.222 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 6847 reflections |
a = 8.436 (2) Å | θ = 3–29° |
b = 18.682 (5) Å | µ = 0.09 mm−1 |
c = 8.427 (3) Å | T = 100 K |
V = 1328.1 (7) Å3 | Block, colorless |
Z = 4 | 0.45 × 0.41 × 0.36 mm |
Kuma KM-4 difractometer with a CCD camera diffractometer | 1699 reflections with I > 2σ(I) |
Radiation source: normal focus sealed tube | Rint = 0.035 |
ω scans | θmax = 28.7°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | h = −9→11 |
Tmin = 0.962, Tmax = 0.969 | k = −24→22 |
9001 measured reflections | l = −11→11 |
1759 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.1971P] where P = (Fo2 + 2Fc2)/3 |
1759 reflections | (Δ/σ)max < 0.001 |
162 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.19 e Å−3 |
C12H24N+·NO3− | V = 1328.1 (7) Å3 |
Mr = 244.33 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 8.436 (2) Å | µ = 0.09 mm−1 |
b = 18.682 (5) Å | T = 100 K |
c = 8.427 (3) Å | 0.45 × 0.41 × 0.36 mm |
Kuma KM-4 difractometer with a CCD camera diffractometer | 1759 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010) | 1699 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.969 | Rint = 0.035 |
9001 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 1 restraint |
wR(F2) = 0.089 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.21 e Å−3 |
1759 reflections | Δρmin = −0.19 e Å−3 |
162 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.67955 (15) | 0.52358 (7) | 0.34329 (17) | 0.0172 (3) | |
H1N | 0.575 (3) | 0.5334 (10) | 0.348 (3) | 0.022 (5)* | |
H2N | 0.703 (2) | 0.5150 (11) | 0.245 (3) | 0.020 (5)* | |
C11 | 0.76844 (18) | 0.58933 (8) | 0.39662 (19) | 0.0174 (3) | |
H11 | 0.8844 | 0.5812 | 0.3802 | 0.021* | |
C21 | 0.7391 (2) | 0.60372 (9) | 0.5718 (2) | 0.0209 (3) | |
H21A | 0.7773 | 0.5626 | 0.6354 | 0.025* | |
H21B | 0.6239 | 0.6091 | 0.5909 | 0.025* | |
C31 | 0.8252 (2) | 0.67195 (8) | 0.6241 (2) | 0.0236 (3) | |
H31A | 0.7994 | 0.6822 | 0.7365 | 0.028* | |
H31B | 0.9411 | 0.6644 | 0.6163 | 0.028* | |
C41 | 0.7782 (2) | 0.73593 (8) | 0.5221 (2) | 0.0249 (3) | |
H41A | 0.8415 | 0.7782 | 0.5537 | 0.030* | |
H41B | 0.6649 | 0.7472 | 0.5400 | 0.030* | |
C51 | 0.8053 (2) | 0.72023 (9) | 0.3456 (2) | 0.0256 (3) | |
H51A | 0.7681 | 0.7613 | 0.2815 | 0.031* | |
H51B | 0.9202 | 0.7140 | 0.3256 | 0.031* | |
C61 | 0.71676 (19) | 0.65265 (8) | 0.2950 (2) | 0.0213 (3) | |
H61A | 0.6012 | 0.6602 | 0.3068 | 0.026* | |
H61B | 0.7390 | 0.6424 | 0.1820 | 0.026* | |
C12 | 0.71252 (17) | 0.45456 (8) | 0.4304 (2) | 0.0173 (3) | |
H12 | 0.6777 | 0.4601 | 0.5432 | 0.021* | |
C22 | 0.61395 (18) | 0.39582 (8) | 0.3534 (2) | 0.0202 (3) | |
H22A | 0.6447 | 0.3906 | 0.2406 | 0.024* | |
H22B | 0.5003 | 0.4089 | 0.3575 | 0.024* | |
C32 | 0.64019 (18) | 0.32501 (8) | 0.4401 (2) | 0.0224 (3) | |
H32A | 0.6010 | 0.3291 | 0.5504 | 0.027* | |
H32B | 0.5791 | 0.2867 | 0.3866 | 0.027* | |
C42 | 0.81560 (18) | 0.30512 (8) | 0.4419 (2) | 0.0225 (3) | |
H42A | 0.8304 | 0.2606 | 0.5040 | 0.027* | |
H42B | 0.8517 | 0.2958 | 0.3320 | 0.027* | |
C52 | 0.91573 (19) | 0.36473 (8) | 0.5142 (2) | 0.0231 (3) | |
H52A | 1.0292 | 0.3516 | 0.5073 | 0.028* | |
H52B | 0.8882 | 0.3701 | 0.6278 | 0.028* | |
C62 | 0.88884 (18) | 0.43628 (8) | 0.4286 (2) | 0.0206 (3) | |
H62A | 0.9496 | 0.4746 | 0.4822 | 0.025* | |
H62B | 0.9266 | 0.4327 | 0.3176 | 0.025* | |
N2 | 0.27878 (15) | 0.55034 (7) | 0.44418 (19) | 0.0209 (3) | |
O1 | 0.15367 (14) | 0.57836 (7) | 0.48831 (17) | 0.0325 (3) | |
O2 | 0.33397 (19) | 0.49638 (8) | 0.51433 (18) | 0.0398 (4) | |
O3 | 0.35579 (15) | 0.57519 (7) | 0.32934 (17) | 0.0318 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0173 (6) | 0.0172 (6) | 0.0172 (7) | 0.0010 (5) | −0.0018 (5) | −0.0027 (5) |
C11 | 0.0183 (7) | 0.0165 (7) | 0.0176 (7) | 0.0002 (5) | −0.0001 (6) | −0.0019 (5) |
C21 | 0.0260 (7) | 0.0202 (7) | 0.0165 (7) | −0.0022 (6) | −0.0009 (6) | −0.0014 (6) |
C31 | 0.0288 (8) | 0.0199 (7) | 0.0220 (8) | 0.0000 (6) | −0.0035 (6) | −0.0047 (6) |
C41 | 0.0274 (8) | 0.0179 (7) | 0.0293 (8) | 0.0012 (6) | −0.0015 (7) | −0.0026 (7) |
C51 | 0.0314 (8) | 0.0209 (7) | 0.0245 (8) | −0.0029 (6) | 0.0017 (7) | 0.0025 (7) |
C61 | 0.0256 (8) | 0.0199 (7) | 0.0184 (7) | 0.0001 (6) | −0.0003 (6) | 0.0021 (6) |
C12 | 0.0170 (6) | 0.0162 (6) | 0.0187 (7) | 0.0009 (5) | −0.0004 (6) | −0.0003 (6) |
C22 | 0.0173 (7) | 0.0189 (7) | 0.0242 (8) | −0.0007 (5) | −0.0013 (6) | −0.0025 (6) |
C32 | 0.0225 (7) | 0.0187 (7) | 0.0261 (8) | −0.0011 (5) | 0.0034 (7) | −0.0007 (6) |
C42 | 0.0236 (7) | 0.0188 (7) | 0.0252 (8) | 0.0017 (6) | 0.0029 (7) | −0.0004 (7) |
C52 | 0.0212 (7) | 0.0227 (7) | 0.0253 (7) | 0.0033 (6) | −0.0045 (6) | 0.0005 (7) |
C62 | 0.0178 (7) | 0.0196 (7) | 0.0243 (8) | 0.0002 (5) | −0.0031 (6) | −0.0009 (6) |
N2 | 0.0202 (6) | 0.0229 (6) | 0.0197 (6) | −0.0009 (5) | −0.0012 (5) | −0.0013 (5) |
O1 | 0.0197 (6) | 0.0370 (7) | 0.0409 (8) | 0.0041 (5) | 0.0034 (5) | −0.0079 (6) |
O2 | 0.0594 (9) | 0.0360 (7) | 0.0239 (6) | 0.0236 (6) | 0.0088 (7) | 0.0071 (6) |
O3 | 0.0296 (6) | 0.0394 (7) | 0.0263 (7) | 0.0000 (5) | 0.0050 (5) | 0.0082 (6) |
N1—C11 | 1.5077 (19) | C12—C22 | 1.522 (2) |
N1—C12 | 1.510 (2) | C12—C62 | 1.526 (2) |
N1—H1N | 0.91 (2) | C12—H12 | 1.0000 |
N1—H2N | 0.86 (2) | C22—C32 | 1.527 (2) |
C11—C21 | 1.521 (2) | C22—H22A | 0.9900 |
C11—C61 | 1.524 (2) | C22—H22B | 0.9900 |
C11—H11 | 1.0000 | C32—C42 | 1.526 (2) |
C21—C31 | 1.532 (2) | C32—H32A | 0.9900 |
C21—H21A | 0.9900 | C32—H32B | 0.9900 |
C21—H21B | 0.9900 | C42—C52 | 1.525 (2) |
C31—C41 | 1.525 (2) | C42—H42A | 0.9900 |
C31—H31A | 0.9900 | C42—H42B | 0.9900 |
C31—H31B | 0.9900 | C52—C62 | 1.536 (2) |
C41—C51 | 1.533 (3) | C52—H52A | 0.9900 |
C41—H41A | 0.9900 | C52—H52B | 0.9900 |
C41—H41B | 0.9900 | C62—H62A | 0.9900 |
C51—C61 | 1.528 (2) | C62—H62B | 0.9900 |
C51—H51A | 0.9900 | N2—O1 | 1.2353 (18) |
C51—H51B | 0.9900 | N2—O3 | 1.255 (2) |
C61—H61A | 0.9900 | N2—O2 | 1.258 (2) |
C61—H61B | 0.9900 | ||
C11—N1—C12 | 117.34 (12) | H61A—C61—H61B | 108.1 |
C11—N1—H1N | 107.9 (13) | N1—C12—C22 | 107.92 (12) |
C12—N1—H1N | 109.3 (13) | N1—C12—C62 | 111.45 (12) |
C11—N1—H2N | 109.0 (14) | C22—C12—C62 | 111.51 (12) |
C12—N1—H2N | 105.4 (14) | N1—C12—H12 | 108.6 |
H1N—N1—H2N | 108 (2) | C22—C12—H12 | 108.6 |
N1—C11—C21 | 110.62 (13) | C62—C12—H12 | 108.6 |
N1—C11—C61 | 108.83 (13) | C12—C22—C32 | 109.96 (13) |
C21—C11—C61 | 111.20 (13) | C12—C22—H22A | 109.7 |
N1—C11—H11 | 108.7 | C32—C22—H22A | 109.7 |
C21—C11—H11 | 108.7 | C12—C22—H22B | 109.7 |
C61—C11—H11 | 108.7 | C32—C22—H22B | 109.7 |
C11—C21—C31 | 110.42 (14) | H22A—C22—H22B | 108.2 |
C11—C21—H21A | 109.6 | C42—C32—C22 | 110.87 (13) |
C31—C21—H21A | 109.6 | C42—C32—H32A | 109.5 |
C11—C21—H21B | 109.6 | C22—C32—H32A | 109.5 |
C31—C21—H21B | 109.6 | C42—C32—H32B | 109.5 |
H21A—C21—H21B | 108.1 | C22—C32—H32B | 109.5 |
C41—C31—C21 | 111.49 (14) | H32A—C32—H32B | 108.1 |
C41—C31—H31A | 109.3 | C52—C42—C32 | 111.30 (13) |
C21—C31—H31A | 109.3 | C52—C42—H42A | 109.4 |
C41—C31—H31B | 109.3 | C32—C42—H42A | 109.4 |
C21—C31—H31B | 109.3 | C52—C42—H42B | 109.4 |
H31A—C31—H31B | 108.0 | C32—C42—H42B | 109.4 |
C31—C41—C51 | 110.99 (13) | H42A—C42—H42B | 108.0 |
C31—C41—H41A | 109.4 | C42—C52—C62 | 111.46 (14) |
C51—C41—H41A | 109.4 | C42—C52—H52A | 109.3 |
C31—C41—H41B | 109.4 | C62—C52—H52A | 109.3 |
C51—C41—H41B | 109.4 | C42—C52—H52B | 109.3 |
H41A—C41—H41B | 108.0 | C62—C52—H52B | 109.3 |
C61—C51—C41 | 110.81 (14) | H52A—C52—H52B | 108.0 |
C61—C51—H51A | 109.5 | C12—C62—C52 | 109.50 (13) |
C41—C51—H51A | 109.5 | C12—C62—H62A | 109.8 |
C61—C51—H51B | 109.5 | C52—C62—H62A | 109.8 |
C41—C51—H51B | 109.5 | C12—C62—H62B | 109.8 |
H51A—C51—H51B | 108.1 | C52—C62—H62B | 109.8 |
C11—C61—C51 | 110.18 (13) | H62A—C62—H62B | 108.2 |
C11—C61—H61A | 109.6 | O1—N2—O3 | 121.19 (15) |
C51—C61—H61A | 109.6 | O1—N2—O2 | 120.95 (16) |
C11—C61—H61B | 109.6 | O3—N2—O2 | 117.86 (14) |
C51—C61—H61B | 109.6 | ||
C12—N1—C11—C21 | −56.99 (17) | C11—N1—C12—C22 | −178.34 (13) |
C12—N1—C11—C61 | −179.43 (13) | C11—N1—C12—C62 | −55.58 (18) |
N1—C11—C21—C31 | −178.14 (13) | N1—C12—C22—C32 | −178.66 (12) |
C61—C11—C21—C31 | −57.10 (18) | C62—C12—C22—C32 | 58.62 (18) |
C11—C21—C31—C41 | 55.47 (18) | C12—C22—C32—C42 | −56.86 (18) |
C21—C31—C41—C51 | −55.0 (2) | C22—C32—C42—C52 | 55.7 (2) |
C31—C41—C51—C61 | 55.81 (19) | C32—C42—C52—C62 | −55.4 (2) |
N1—C11—C61—C51 | −179.74 (13) | N1—C12—C62—C52 | −178.37 (13) |
C21—C11—C61—C51 | 58.16 (18) | C22—C12—C62—C52 | −57.70 (18) |
C41—C51—C61—C11 | −57.12 (18) | C42—C52—C62—C12 | 55.69 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.91 (2) | 2.56 (2) | 3.292 (2) | 138.2 (17) |
N1—H1N···O3 | 0.91 (2) | 2.01 (2) | 2.8988 (19) | 166.7 (19) |
N1—H2N···O2i | 0.86 (2) | 1.98 (2) | 2.799 (2) | 157.6 (19) |
C11—H11···O1ii | 1.00 | 2.45 | 3.347 (2) | 149 |
C12—H12···O3iii | 1.00 | 2.52 | 3.456 (3) | 156 |
C22—H22B···O2 | 0.99 | 2.53 | 3.309 (2) | 136 |
C62—H62A···O1ii | 0.99 | 2.59 | 3.506 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x+1, y, z; (iii) −x+1, −y+1, z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2 | 0.91 (2) | 2.56 (2) | 3.292 (2) | 138.2 (17) |
N1—H1N···O3 | 0.91 (2) | 2.01 (2) | 2.8988 (19) | 166.7 (19) |
N1—H2N···O2i | 0.86 (2) | 1.98 (2) | 2.799 (2) | 157.6 (19) |
C11—H11···O1ii | 1.00 | 2.45 | 3.347 (2) | 149 |
C12—H12···O3iii | 1.00 | 2.52 | 3.456 (3) | 156 |
C22—H22B···O2 | 0.99 | 2.53 | 3.309 (2) | 136 |
C62—H62A···O1ii | 0.99 | 2.59 | 3.506 (2) | 153 |
Symmetry codes: (i) −x+1, −y+1, z−1/2; (ii) x+1, y, z; (iii) −x+1, −y+1, z+1/2. |
Acknowledgements
Financial support by a statutory activity subsidy from the Polish Ministry of Science and Higher Education for the Department of Chemistry of Wrocław University of Technology is gratefully acknowledged.
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