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

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Crystal structure of cyclo­hexyl­ammonium thio­cyanate

aNational Petrochemical Technology Center (NPTC), Materials Science Research Institute (MSRI), King Abdulaziz City for Science and Technology (KACST), PO Box 6086, Riyadh 11442, Saudi Arabia, bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Chemistry, Alva's Institute of Engineering & Technology, Mijar, Moodbidri 574225, Karnataka, India
*Correspondence e-mail: hfun.c@ksu.edu.sa

Edited by J. Simpson, University of Otago, New Zealand (Received 6 December 2014; accepted 14 December 2014; online 1 January 2015)

In the title salt, C6H11NH3+·SCN, the cyclo­hexyl­ammonium ring adopts a slightly distorted chair conformation. The ammonium group occupies an equatorial position to minimize 1,3 and 1,5 diaxial inter­actions. In the crystal, the components are linked by N—H⋯N and N—H⋯S hydrogen-bonding inter­actions, resulting in a three-dimensional network.

1. Related literature

For the synthesis and uses of the title compound, see: Baluja et al. (1960[Baluja, G., Chase, B. H., Kenner, G. W. & Todd, A. (1960). J. Chem. Soc. pp. 4678-4681.]); Coddens et al. (1986[Coddens, M. E., Furton, K. G. & Poole, C. F. (1986). J. Chromatogr. A, 356, 59-77.]); Goel (1988[Goel, A. B. (1988). US Patent 4 775 735.]); Mathes et al. (1948[Mathes, R. A., Stewart, F. D. & Swedish, F. Jr (1948). J. Am. Chem. Soc. 70, 3455.]) 1955[Mathes, R. A. & Stewart, F. D. (1955). US Patent 2 704 752.]); Mathes & Stewart (1955[Mathes, R. A. & Stewart, F. D. (1955). US Patent 2 704 752.]); Morrison & Ratcliffe (1953[Morrison, A. L. & Ratcliffe, F. (1953). GB Patent 697 473.]); Stewart (1951[Stewart, F. D. (1951). US Patent 2 547 722.]); For the structures of other cyclo­hexyl­ammonium salts, see: Bagabas et al. (2014[Bagabas, A. A., Aboud, M. F. A., Shemsi, A. M., Addurihem, E. S., Al-Othman, Z. A., Chidan Kumar, C. S. & Fun, H.-K. (2014). Acta Cryst. E70, o253-o254.]); Shimada et al. (1955[Shimada, A., Okaya, Y. & Nakaura, M. (1955). Acta Cryst. 8, 819-822.]); Smith et al. (1994[Smith, H. W., Mastropaolo, D., Camerman, A. & Camerman, N. (1994). J. Chem. Crystallogr. 24, 239-242.]); Odendal et al. (2010[Odendal, J. A., Bruce, J. C., Koch, K. R. & Haynes, D. A. (2010). CrystEngComm, 12, 2398-2408.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C6H14N+·NCS

  • Mr = 158.26

  • Trigonal, [R \overline 3]

  • a = 23.4036 (6) Å

  • c = 8.3373 (2) Å

  • V = 3954.8 (2) Å3

  • Z = 18

  • Cu Kα radiation

  • μ = 2.71 mm−1

  • T = 296 K

  • 0.98 × 0.25 × 0.11 mm

2.2. Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.176, Tmax = 0.748

  • 10355 measured reflections

  • 1670 independent reflections

  • 1530 reflections with I > 2σ(I)

  • Rint = 0.051

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 0.100

  • S = 1.06

  • 1670 reflections

  • 103 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1N⋯S1i 0.89 (2) 2.62 (2) 3.4955 (14) 167 (2)
N1—H2N⋯N2 0.90 (2) 1.94 (2) 2.822 (2) 170.4 (18)
N1—H3N⋯S1ii 0.87 (2) 2.573 (18) 3.4214 (14) 165.5 (19)
Symmetry codes: (i) [x-y+{\script{2\over 3}}, x+{\script{1\over 3}}, -z+{\script{4\over 3}}]; (ii) [-x+{\script{1\over 3}}, -y+{\script{2\over 3}}, -z+{\script{2\over 3}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Chemical context top

The title compound, C6H11NH3+.SCN-, has previously been synthesized by reacting an aqueous solution of cyclo­hexyl­amine (CHA) with ammonium thio­cyanate (H4N+SCN-) at 85–90 °C, followed by extraction of C6H11NH3+.SCN- with benzene, and then recrystallization from ethanol (Mathes et al., 1948). This compound is used as an animal repellent and also as an insecticide or fungicide (Stewart, 1951). It is also a starting material for the preparation of other compounds (Baluja et al., 1960; Morrison et al., 1953; Stewart, 1951), an accelerator and activator for rubber vulcanization (Mathes et al., 1955) and an accelerator for the curing of polyepoxide-polyimine materials (Goel, 1988). It has also been used as a stationary phase for gas chromatography (Coddens et al., 1986). Nevertheless, the crystal structure of this important compound has not been determined. We report here the crystal structure of C6H11NH3+.SCN- together with a new room-temperature synthesis using a salt metathesis reaction. This is a simpler process and results in a higher yield than the one published in the literature. Furthermore, we aim to use this compound to prepare new metal complexes based on both the cyclo­hexyl­ammonium cation and the thio­cyanate anion.

Structural commentary top

The assymmetric unit of the title compound (Fig. 1), contains one cyclo­hexyl­ammonium cation (C1–C6/N1) and one thio­cynate anion (S1/C7/N2). The cyclo­hexyl­ammonium ring adopts a slightly distorted chair conformation, with puckering parameters: Q = 0.5669 (18) Å, θ = 177.95 (18)°, and φ = 161 (5)°. For an ideal chair configuration, θ has a value of 0 or 180°. The ammonium functional group is at an equatorial position to minimize 1,3 and 1,5 di-axial inter­actions. The bond lengths and bond angles are in normal ranges and are comparable with those reported earlier for similar compounds (Bagabas et al., 2014; Shimada et al., 1955; Smith et al., 1994; Odendal et al., 2010).

Supra­molecular features top

In the asymmetric unit, a strong N1–H2N···N2 hydrogen bond links the cation and the anion. In the crystal structure, these contacts are supported by inter­molecular N1–H1N···S1 and N1–H3N···S1 hydrogen bonds (Symmetry codes: x-y+2/3, x+1/3, -z+4/3; -x+1/3, -y+2/3, -z+2/3) with S1 as a bifurcated acceptor (Fig. 2) to produce a three-dimensional network.

Synthesis and crystallization top

The title compound, C6H11NH3+.SCN-, was prepared by exchanging counter ions in a salt metathesis reaction between sodium thio­cyanate (NaSCN) and cyclo­hexyl­ammonium chloride (C6H11NH3+. Cl-) in ethano­lic medium, where the precipitation of sodium chloride (NaCl) is the driving force for the reaction. In typical reaction, 100 mmol of NaSCN was dissolved in 350 ml absolute ethanol, while 100 mmol C6H11NH3+Cl- was dissolved separately in 250 ml absolute ethanol. Combining these two solutions at room temperature resulted in white precipitate of NaCl, as confirmed by X-ray powder diffraction (PXRD), which was filtered off through F-size fritted filter. The filtrate was left for the solvent to evaporate to dryness at room temperature. About 200 ml absolute ethanol was added to the residual solid to dissolve the desired product, C6H11NH3+.SCN-. It was noticed at this step that a small amount of the residual solid did not dissolve and it was separated by filtration. This undissolved material was NaCl, again identified by PXRD. Slow evaporation at room temperature over a period of 10 days of the ethano­lic solution resluted in colorless crystals of C6H11NH3+.SCN- (yield = around 100%) suitable for single crystal X-ray diffraction studies. It is advisable to recrystallize this light-sensitive material in the dark. The chemical composition of the desired product was also confirmed by C, H, N, S elemental microanalysis: (%C: 52.67 exp.; 53.11 cal.), (%H: 9.30 exp.; 8.93 cal.), (%N: 17.85 exp.; 17.70 cal.), and (%S: 20.18 exp.; 20.25 cal.). Potassium thio­cyanate (KSCN) can be used instead of NaSCN for executing the reaction, where KCl precipitates and C6H11NH3+.SCN- produces with around 98% yield.

Refinement details top

The nitro­gen-bound H-atoms were located in a difference Fourier map and were refined freely (NH = 0.87 (2), 0.90 (2) and 0.89 (2) Å). Other H atoms were positioned geometrically (C—H 0.97–0.98 Å) and refined using a riding model with Uiso(H) = 1.2 Ueq(C)

Related literature top

For the synthesis and uses of the title compound, see: Baluja et al. (1960); Coddens et al. (1986); Goel (1988); Mathes et al. (1948) 1955); Mathes & Stewart (1955); Morrison & Ratcliffe (1953); Stewart (1951); For the structures of other cyclohexylammonium salts, see: Bagabas et al. (2014); Shimada et al. (1955); Smith et al. (1994); Odendal et al. (2010).

Structure description top

The title compound, C6H11NH3+.SCN-, has previously been synthesized by reacting an aqueous solution of cyclo­hexyl­amine (CHA) with ammonium thio­cyanate (H4N+SCN-) at 85–90 °C, followed by extraction of C6H11NH3+.SCN- with benzene, and then recrystallization from ethanol (Mathes et al., 1948). This compound is used as an animal repellent and also as an insecticide or fungicide (Stewart, 1951). It is also a starting material for the preparation of other compounds (Baluja et al., 1960; Morrison et al., 1953; Stewart, 1951), an accelerator and activator for rubber vulcanization (Mathes et al., 1955) and an accelerator for the curing of polyepoxide-polyimine materials (Goel, 1988). It has also been used as a stationary phase for gas chromatography (Coddens et al., 1986). Nevertheless, the crystal structure of this important compound has not been determined. We report here the crystal structure of C6H11NH3+.SCN- together with a new room-temperature synthesis using a salt metathesis reaction. This is a simpler process and results in a higher yield than the one published in the literature. Furthermore, we aim to use this compound to prepare new metal complexes based on both the cyclo­hexyl­ammonium cation and the thio­cyanate anion.

The assymmetric unit of the title compound (Fig. 1), contains one cyclo­hexyl­ammonium cation (C1–C6/N1) and one thio­cynate anion (S1/C7/N2). The cyclo­hexyl­ammonium ring adopts a slightly distorted chair conformation, with puckering parameters: Q = 0.5669 (18) Å, θ = 177.95 (18)°, and φ = 161 (5)°. For an ideal chair configuration, θ has a value of 0 or 180°. The ammonium functional group is at an equatorial position to minimize 1,3 and 1,5 di-axial inter­actions. The bond lengths and bond angles are in normal ranges and are comparable with those reported earlier for similar compounds (Bagabas et al., 2014; Shimada et al., 1955; Smith et al., 1994; Odendal et al., 2010).

In the asymmetric unit, a strong N1–H2N···N2 hydrogen bond links the cation and the anion. In the crystal structure, these contacts are supported by inter­molecular N1–H1N···S1 and N1–H3N···S1 hydrogen bonds (Symmetry codes: x-y+2/3, x+1/3, -z+4/3; -x+1/3, -y+2/3, -z+2/3) with S1 as a bifurcated acceptor (Fig. 2) to produce a three-dimensional network.

For the synthesis and uses of the title compound, see: Baluja et al. (1960); Coddens et al. (1986); Goel (1988); Mathes et al. (1948) 1955); Mathes & Stewart (1955); Morrison & Ratcliffe (1953); Stewart (1951); For the structures of other cyclohexylammonium salts, see: Bagabas et al. (2014); Shimada et al. (1955); Smith et al. (1994); Odendal et al. (2010).

Synthesis and crystallization top

The title compound, C6H11NH3+.SCN-, was prepared by exchanging counter ions in a salt metathesis reaction between sodium thio­cyanate (NaSCN) and cyclo­hexyl­ammonium chloride (C6H11NH3+. Cl-) in ethano­lic medium, where the precipitation of sodium chloride (NaCl) is the driving force for the reaction. In typical reaction, 100 mmol of NaSCN was dissolved in 350 ml absolute ethanol, while 100 mmol C6H11NH3+Cl- was dissolved separately in 250 ml absolute ethanol. Combining these two solutions at room temperature resulted in white precipitate of NaCl, as confirmed by X-ray powder diffraction (PXRD), which was filtered off through F-size fritted filter. The filtrate was left for the solvent to evaporate to dryness at room temperature. About 200 ml absolute ethanol was added to the residual solid to dissolve the desired product, C6H11NH3+.SCN-. It was noticed at this step that a small amount of the residual solid did not dissolve and it was separated by filtration. This undissolved material was NaCl, again identified by PXRD. Slow evaporation at room temperature over a period of 10 days of the ethano­lic solution resluted in colorless crystals of C6H11NH3+.SCN- (yield = around 100%) suitable for single crystal X-ray diffraction studies. It is advisable to recrystallize this light-sensitive material in the dark. The chemical composition of the desired product was also confirmed by C, H, N, S elemental microanalysis: (%C: 52.67 exp.; 53.11 cal.), (%H: 9.30 exp.; 8.93 cal.), (%N: 17.85 exp.; 17.70 cal.), and (%S: 20.18 exp.; 20.25 cal.). Potassium thio­cyanate (KSCN) can be used instead of NaSCN for executing the reaction, where KCl precipitates and C6H11NH3+.SCN- produces with around 98% yield.

Refinement details top

The nitro­gen-bound H-atoms were located in a difference Fourier map and were refined freely (NH = 0.87 (2), 0.90 (2) and 0.89 (2) Å). Other H atoms were positioned geometrically (C—H 0.97–0.98 Å) and refined using a riding model with Uiso(H) = 1.2 Ueq(C)

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with atom labels and 50% probability displacement ellipsoids. The strong N—H···N hydrogen bond linking the cation and the anion is shown as a dashed line.
[Figure 2] Fig. 2. Crystal packing of the title compound, showing the N–H···N and N–H···S hydrogen bonding interactions (see Table 1) as dashed lines producing a three-dimensional network
Cyclohexylammonium thiocyanate top
Crystal data top
C6H14N+·NCSDx = 1.196 Mg m3
Mr = 158.26Cu Kα radiation, λ = 1.54178 Å
Trigonal, R3:HCell parameters from 3689 reflections
a = 23.4036 (6) Åθ = 3.8–71.3°
c = 8.3373 (2) ŵ = 2.71 mm1
V = 3954.8 (2) Å3T = 296 K
Z = 18Needle, colourless
F(000) = 15480.98 × 0.25 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
1530 reflections with I > 2σ(I)
φ and ω scansRint = 0.051
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
θmax = 72.1°, θmin = 3.8°
Tmin = 0.176, Tmax = 0.748h = 2828
10355 measured reflectionsk = 2828
1670 independent reflectionsl = 79
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100 w = 1/[σ2(Fo2) + (0.0622P)2 + 1.6831P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max < 0.001
1670 reflectionsΔρmax = 0.22 e Å3
103 parametersΔρmin = 0.28 e Å3
Crystal data top
C6H14N+·NCSZ = 18
Mr = 158.26Cu Kα radiation
Trigonal, R3:Hµ = 2.71 mm1
a = 23.4036 (6) ÅT = 296 K
c = 8.3373 (2) Å0.98 × 0.25 × 0.11 mm
V = 3954.8 (2) Å3
Data collection top
Bruker APEXII CCD
diffractometer
1670 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
1530 reflections with I > 2σ(I)
Tmin = 0.176, Tmax = 0.748Rint = 0.051
10355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.22 e Å3
1670 reflectionsΔρmin = 0.28 e Å3
103 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
S10.06708 (2)0.40416 (2)0.39763 (4)0.04932 (18)
N10.22496 (6)0.30544 (6)0.62467 (16)0.0396 (3)
N20.15453 (8)0.36894 (8)0.5327 (2)0.0628 (4)
C10.17544 (6)0.24495 (6)0.71255 (15)0.0339 (3)
H1A0.15410.25820.79390.041*
C20.12316 (7)0.19773 (7)0.59728 (17)0.0433 (3)
H2A0.14370.18620.51190.052*
H2B0.10050.21870.54960.052*
C30.07361 (7)0.13543 (8)0.6863 (2)0.0525 (4)
H3A0.04940.14650.76260.063*
H3B0.04220.10410.61020.063*
C40.10721 (9)0.10360 (7)0.7747 (2)0.0570 (4)
H4A0.12640.08710.69730.068*
H4B0.07460.06640.83640.068*
C50.16092 (8)0.15210 (8)0.88648 (19)0.0502 (4)
H5A0.18360.13120.93450.060*
H5B0.14100.16430.97210.060*
C60.21055 (7)0.21389 (7)0.79664 (18)0.0422 (3)
H6A0.24270.24520.87150.051*
H6B0.23390.20250.71840.051*
C70.11856 (7)0.38340 (7)0.47760 (17)0.0426 (3)
H3N0.2412 (9)0.2942 (10)0.545 (2)0.055 (5)*
H2N0.2062 (9)0.3280 (9)0.587 (2)0.046 (4)*
H1N0.2572 (10)0.3321 (10)0.691 (3)0.061 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0485 (2)0.0679 (3)0.0414 (3)0.03650 (19)0.00383 (14)0.00618 (15)
N10.0367 (6)0.0371 (6)0.0419 (7)0.0162 (5)0.0010 (5)0.0025 (5)
N20.0598 (8)0.0673 (9)0.0734 (10)0.0408 (8)0.0064 (7)0.0012 (7)
C10.0320 (6)0.0350 (6)0.0344 (7)0.0165 (5)0.0010 (5)0.0007 (5)
C20.0362 (7)0.0460 (7)0.0398 (8)0.0145 (6)0.0040 (5)0.0015 (6)
C30.0374 (7)0.0488 (8)0.0518 (9)0.0070 (6)0.0015 (6)0.0043 (7)
C40.0615 (9)0.0362 (7)0.0624 (10)0.0162 (7)0.0150 (8)0.0050 (7)
C50.0567 (9)0.0488 (8)0.0500 (9)0.0299 (7)0.0048 (7)0.0119 (6)
C60.0379 (7)0.0437 (7)0.0469 (8)0.0218 (6)0.0034 (6)0.0032 (6)
C70.0416 (7)0.0437 (7)0.0417 (8)0.0207 (6)0.0031 (6)0.0006 (6)
Geometric parameters (Å, º) top
S1—C71.6486 (15)C3—C41.517 (3)
N1—C11.4978 (16)C3—H3A0.9700
N1—H3N0.87 (2)C3—H3B0.9700
N1—H2N0.90 (2)C4—C51.520 (2)
N1—H1N0.89 (2)C4—H4A0.9700
N2—C71.148 (2)C4—H4B0.9700
C1—C21.5132 (18)C5—C61.524 (2)
C1—C61.5142 (18)C5—H5A0.9700
C1—H1A0.9800C5—H5B0.9700
C2—C31.527 (2)C6—H6A0.9700
C2—H2A0.9700C6—H6B0.9700
C2—H2B0.9700
C1—N1—H3N109.8 (13)C2—C3—H3B109.2
C1—N1—H2N110.7 (11)H3A—C3—H3B107.9
H3N—N1—H2N108.9 (17)C3—C4—C5111.65 (13)
C1—N1—H1N109.9 (13)C3—C4—H4A109.3
H3N—N1—H1N110.1 (18)C5—C4—H4A109.3
H2N—N1—H1N107.5 (16)C3—C4—H4B109.3
N1—C1—C2109.91 (11)C5—C4—H4B109.3
N1—C1—C6109.33 (11)H4A—C4—H4B108.0
C2—C1—C6112.22 (11)C4—C5—C6111.14 (13)
N1—C1—H1A108.4C4—C5—H5A109.4
C2—C1—H1A108.4C6—C5—H5A109.4
C6—C1—H1A108.4C4—C5—H5B109.4
C1—C2—C3109.83 (11)C6—C5—H5B109.4
C1—C2—H2A109.7H5A—C5—H5B108.0
C3—C2—H2A109.7C1—C6—C5110.12 (11)
C1—C2—H2B109.7C1—C6—H6A109.6
C3—C2—H2B109.7C5—C6—H6A109.6
H2A—C2—H2B108.2C1—C6—H6B109.6
C4—C3—C2111.86 (13)C5—C6—H6B109.6
C4—C3—H3A109.2H6A—C6—H6B108.2
C2—C3—H3A109.2N2—C7—S1179.71 (16)
C4—C3—H3B109.2
N1—C1—C2—C3178.72 (12)C3—C4—C5—C654.67 (18)
C6—C1—C2—C356.83 (16)N1—C1—C6—C5179.85 (12)
C1—C2—C3—C454.73 (17)C2—C1—C6—C557.63 (16)
C2—C3—C4—C554.43 (18)C4—C5—C6—C155.66 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.89 (2)2.62 (2)3.4955 (14)167 (2)
N1—H2N···N20.90 (2)1.94 (2)2.822 (2)170.4 (18)
N1—H3N···S1ii0.87 (2)2.573 (18)3.4214 (14)165.5 (19)
Symmetry codes: (i) xy+2/3, x+1/3, z+4/3; (ii) x+1/3, y+2/3, z+2/3.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···S1i0.89 (2)2.62 (2)3.4955 (14)167 (2)
N1—H2N···N20.90 (2)1.94 (2)2.822 (2)170.4 (18)
N1—H3N···S1ii0.87 (2)2.573 (18)3.4214 (14)165.5 (19)
Symmetry codes: (i) xy+2/3, x+1/3, z+4/3; (ii) x+1/3, y+2/3, z+2/3.
 

Footnotes

Additonal correspondence author, e-mail: abagbas@kacst.edu.sa.

§Thomson Reuters ResearcherID: C-3194-2011.

Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors extend their appreciation to King Abdulaziz City for Science and Technology (KACST) for funding this work through project number 29–280. CSCK thanks Universiti Sains Malaysia (USM) for a postdoctoral research fellowship.

References

First citationBagabas, A. A., Aboud, M. F. A., Shemsi, A. M., Addurihem, E. S., Al-Othman, Z. A., Chidan Kumar, C. S. & Fun, H.-K. (2014). Acta Cryst. E70, o253–o254.  CSD CrossRef IUCr Journals Google Scholar
First citationBaluja, G., Chase, B. H., Kenner, G. W. & Todd, A. (1960). J. Chem. Soc. pp. 4678–4681.  CrossRef Google Scholar
First citationBruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCoddens, M. E., Furton, K. G. & Poole, C. F. (1986). J. Chromatogr. A, 356, 59–77.  CrossRef CAS Google Scholar
First citationGoel, A. B. (1988). US Patent 4 775 735.  Google Scholar
First citationMathes, R. A. & Stewart, F. D. (1955). US Patent 2 704 752.  Google Scholar
First citationMathes, R. A., Stewart, F. D. & Swedish, F. Jr (1948). J. Am. Chem. Soc. 70, 3455.  CrossRef PubMed Google Scholar
First citationMorrison, A. L. & Ratcliffe, F. (1953). GB Patent 697 473.  Google Scholar
First citationOdendal, J. A., Bruce, J. C., Koch, K. R. & Haynes, D. A. (2010). CrystEngComm, 12, 2398–2408.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShimada, A., Okaya, Y. & Nakaura, M. (1955). Acta Cryst. 8, 819–822.  CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
First citationSmith, H. W., Mastropaolo, D., Camerman, A. & Camerman, N. (1994). J. Chem. Crystallogr. 24, 239–242.  CSD CrossRef CAS Web of Science Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStewart, F. D. (1951). US Patent 2 547 722.  Google Scholar

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