Cyclo­hexyl­ammonium acetate–N,N′,N′′-tricyclo­hexyl­phospho­ric triamide (1/1)

Pourayoubi, M.; Keikha, M.; Rheingold, A.L.; Golen, J.A.

doi:10.1107/S1600536812028589

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2266

https://doi.org/10.1107/S1600536812028589

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Cyclohexylammonium acetate–N,N′,N′′-tricyclohexylphosphoric triamide (1/1)

Mehrdad Pourayoubi,^a Mojtaba Keikha,^a ^* Arnold L. Rheingold ^b and James A. Golen ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^bDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: Mojtaba.keikha@yahoo.com

(Received 7 June 2012; accepted 23 June 2012; online 30 June 2012)

In the phosphoric triamide molecule of the title compound, C₆H₁₄N⁺·C₂H₃O₂⁻·C₁₈H₃₆N₃OP, the P atom displays a distorted tetrahedral geometry and the cyclohexyl rings adopt chair conformations with the NH groups in equatorial positions. In the crystal, the cations, anions and phosphoric triamide molecules are linked via N—H⋯O hydrogen bonds into a two-dimensional array parallel to the bc plane. The O atom of the P(O) group acts as a double-hydrogen-bond acceptor.

Related literature

For background to phosphoric triamide molecules and for bond lengths and angles in related structures, see: Pourayoubi, Tarahhomi et al. (2012 ); Sabbaghi et al. (2011 ). For a definition of double-hydrogen-bond acceptor, see: Pourayoubi, Nečas & Negari (2012 ). For hydrolysis of compounds containing a C≡N bond, see: Vollhardt & Schore (1998 ).

Experimental

Crystal data

C₆H₁₄N⁺·C₂H₃O₂⁻·C₁₈H₃₆N₃OP
M_r = 500.69
Monoclinic, P 2₁ /c
a = 12.7663 (8) Å
b = 10.9011 (7) Å
c = 21.2791 (13) Å
β = 104.523 (3)°
V = 2866.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 90 K
0.35 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.957, T_max = 0.975
21979 measured reflections
5898 independent reflections
4702 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 0.97
5898 reflections
326 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.87 (1)	2.14 (2)	3.0049 (18)	171 (2)
N3—H3N⋯O2ⁱⁱ	0.84 (1)	2.05 (2)	2.8837 (18)	173 (2)
N1—H1N⋯O3	0.86 (1)	2.21 (2)	3.0394 (18)	163 (2)
N4—H4NC⋯O1ⁱⁱⁱ	0.89 (1)	2.05 (2)	2.9445 (18)	178 (2)
N4—H4NB⋯O3^iv	0.89 (2)	1.94 (2)	2.7666 (19)	155 (2)
N4—H4NA⋯O2^v	0.88 (2)	1.83 (2)	2.6992 (19)	169 (2)
Symmetry codes: (i) -x, -y, -z; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x+1, y+1, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028589/ff2071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028589/ff2071Isup2.hkl

checkCIF report

Comment top

The X-ray determination of the title co-crystal, P(O)(NHC₆H₁₁)₃,(C₆H₁₁NH₃⁺)(CH₃COO^-), (Fig. 1) was performed following to our previous study on synthesis and crystal structure determination of phosphoric triamide compounds (Pourayoubi, Tarahhomi et al., 2012 and Sabbaghi et al., 2011).

The cyclohexyl rings of phosphoric triamide molecule and also in the C₆H₁₁NH₃⁺ cation have the chair conformation and the NH and NH₃⁺ groups are in the equatorial position of the rings. In P(O)(NHC₆H₁₁)₃, the P atom exists in a distorted tetrahedral environment with the P—N bond lengths of 1.6315 (14) Å, 1.6440 (14) Å and 1.6463 (14) Å (for P1—N1). The P═O bond length and the P—N—C bond angles are standard for the phosphoric triamides (Pourayoubi, Tarahhomi et al., 2012 and Sabbaghi et al., 2011).

In the crystal, the oxygen atom of the P═O group acts as a double-hydrogen bond acceptor (Pourayoubi, Nečas & Negari, 2012), forming the P═O···[H—N][H—N] grouping with one N—H unit of a neighboring P(O)(NHC₆H₁₁)₃ molecule and one N—H unit of C₆H₁₁NH₃⁺ cation. Other N—H units of P(O)(NHC₆H₁₁)₃ and N—H units of C₆H₁₁NH₃⁺ are involved in the N—H···O hydrogen bonds with the O atoms of acetate anion. These N—H···O hydrogen bonds form a two-dimensional arrangement parallel to bc plane (Fig. 2).

Related literature top

For background to phosphoric triamide molecules and for bond lengths and angles in related structures, see: Pourayoubi, Tarahhomi et al. (2012); Sabbaghi et al. (2011). For a definition of double-hydrogen-bond acceptor, see: Pourayoubi, Nečas & Negari (2012). For hydrolysis of compounds containing a C≡N bond, see: Vollhardt & Schore (1998).

Experimental top

The title co-crystal was obtained fortuitously from a reaction between phosphoryl chloride and cyclohexylamine in acetonitrile at 273 K (4 h) and then the treatment of dibenzylamine at ice bath temperature. The presence of acetate anion is attributed to the hydrolysis of acetonitrile in acidic media of reaction (Vollhardt & Schore, 1998).

Structure description top

For background to phosphoric triamide molecules and for bond lengths and angles in related structures, see: Pourayoubi, Tarahhomi et al. (2012); Sabbaghi et al. (2011). For a definition of double-hydrogen-bond acceptor, see: Pourayoubi, Nečas & Negari (2012). For hydrolysis of compounds containing a C≡N bond, see: Vollhardt & Schore (1998).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. An ORTEP-style plot and atom labeling scheme for the title cocrystal. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. A view of the two-dimensional arrangement with the N—H···O hydrogen bonds parallel to bc plane. The N–H···O hydrogen bonds are shown as dashed lines and the H atoms bound to C atoms have been omitted for clarity.

Cyclohexylammonium acetate–N,N',N''-tricyclohexylphosphoric triamide (1/1) top

Crystal data top

C₆H₁₄N⁺·C₂H₃O₂⁻·C₁₈H₃₆N₃OP	F(000) = 1104
M_r = 500.69	D_x = 1.160 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4565 reflections
a = 12.7663 (8) Å	θ = 2.5–26.4°
b = 10.9011 (7) Å	µ = 0.13 mm⁻¹
c = 21.2791 (13) Å	T = 90 K
β = 104.523 (3)°	Block, colourless
V = 2866.7 (3) Å³	0.35 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5898 independent reflections
Radiation source: fine-focus sealed tube	4702 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 26.5°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −13→16
T_min = 0.957, T_max = 0.975	k = −12→13
21979 measured reflections	l = −25→26

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ²(F_o²) + (0.0636P)² + 1.5804P] where P = (F_o² + 2F_c²)/3
5898 reflections	(Δ/σ)_max < 0.001
326 parameters	Δρ_max = 0.47 e Å⁻³
6 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₆H₁₄N⁺·C₂H₃O₂⁻·C₁₈H₃₆N₃OP	V = 2866.7 (3) Å³
M_r = 500.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.7663 (8) Å	µ = 0.13 mm⁻¹
b = 10.9011 (7) Å	T = 90 K
c = 21.2791 (13) Å	0.35 × 0.25 × 0.20 mm
β = 104.523 (3)°

Data collection top

Bruker APEXII CCD diffractometer	5898 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4702 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.975	R_int = 0.043
21979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	6 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.47 e Å⁻³
5898 reflections	Δρ_min = −0.47 e Å⁻³
326 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

	x	y	z	U_iso*/U_eq
P1	0.03749 (3)	0.03310 (4)	0.110490 (19)	0.01413 (12)
O1	−0.03516 (9)	−0.06943 (10)	0.07941 (5)	0.0162 (3)
O2	−0.03699 (11)	0.56848 (11)	0.20581 (6)	0.0235 (3)
O3	0.03597 (10)	0.39451 (11)	0.18349 (6)	0.0226 (3)
N1	−0.03942 (11)	0.14670 (13)	0.12349 (6)	0.0162 (3)
H1N	−0.0051 (14)	0.2092 (15)	0.1427 (9)	0.019*
N2	0.12192 (11)	0.06325 (12)	0.06552 (7)	0.0153 (3)
H2N	0.0942 (14)	0.0571 (17)	0.0240 (7)	0.018*
N3	0.11772 (11)	0.01218 (13)	0.18250 (7)	0.0169 (3)
H3N	0.0902 (15)	0.0241 (18)	0.2140 (8)	0.020*
N4	0.90968 (12)	0.80813 (14)	0.19022 (7)	0.0175 (3)
H4NC	0.9261 (15)	0.8438 (17)	0.1561 (8)	0.021*
H4NB	0.9447 (14)	0.8426 (17)	0.2274 (8)	0.021*
H4NA	0.9338 (15)	0.7323 (14)	0.1928 (9)	0.021*
C1	0.21703 (13)	−0.06129 (15)	0.19470 (8)	0.0165 (3)
H1A	0.2472	−0.0528	0.1558	0.020*
C2	0.19909 (15)	−0.19790 (16)	0.20397 (9)	0.0223 (4)
H2B	0.1455	−0.2303	0.1656	0.027*
H2A	0.1701	−0.2100	0.2425	0.027*
C3	0.30587 (16)	−0.26732 (17)	0.21303 (9)	0.0277 (4)
H3B	0.2940	−0.3549	0.2216	0.033*
H3A	0.3301	−0.2625	0.1724	0.033*
C4	0.39406 (16)	−0.21611 (18)	0.26870 (9)	0.0279 (4)
H4A	0.3752	−0.2326	0.3103	0.033*
H4B	0.4632	−0.2582	0.2699	0.033*
C5	0.40827 (15)	−0.07895 (19)	0.26147 (9)	0.0281 (4)
H5A	0.4379	−0.0634	0.2235	0.034*
H5B	0.4608	−0.0473	0.3005	0.034*
C6	0.30118 (14)	−0.01101 (17)	0.25267 (9)	0.0237 (4)
H6A	0.2747	−0.0201	0.2924	0.028*
H6B	0.3124	0.0775	0.2461	0.028*
C7	0.21298 (13)	0.14884 (15)	0.08461 (8)	0.0156 (3)
H7A	0.2431	0.1405	0.1325	0.019*
C8	0.30137 (13)	0.11132 (16)	0.05214 (8)	0.0192 (4)
H8A	0.2731	0.1162	0.0044	0.023*
H8B	0.3223	0.0251	0.0635	0.023*
C9	0.40097 (15)	0.19339 (17)	0.07308 (10)	0.0262 (4)
H9A	0.4355	0.1792	0.1196	0.031*
H9B	0.4538	0.1712	0.0480	0.031*
C10	0.37214 (15)	0.32891 (17)	0.06253 (9)	0.0251 (4)
H10A	0.4371	0.3793	0.0810	0.030*
H10B	0.3485	0.3460	0.0154	0.030*
C11	0.28244 (15)	0.36423 (16)	0.09441 (9)	0.0244 (4)
H11A	0.2623	0.4511	0.0845	0.029*
H11B	0.3090	0.3560	0.1421	0.029*
C12	0.18287 (14)	0.28355 (15)	0.07060 (9)	0.0208 (4)
H12A	0.1533	0.2954	0.0233	0.025*
H12B	0.1264	0.3074	0.0928	0.025*
C13	−0.13969 (13)	0.17719 (15)	0.07496 (8)	0.0165 (3)
H13A	−0.1773	0.0984	0.0591	0.020*
C14	−0.12088 (14)	0.24561 (16)	0.01597 (8)	0.0181 (4)
H14A	−0.0792	0.3214	0.0306	0.022*
H14B	−0.0775	0.1935	−0.0061	0.022*
C15	−0.22712 (15)	0.27884 (16)	−0.03186 (8)	0.0226 (4)
H15A	−0.2644	0.2028	−0.0508	0.027*
H15B	−0.2119	0.3280	−0.0677	0.027*
C16	−0.30106 (15)	0.35149 (18)	0.00041 (9)	0.0256 (4)
H16A	−0.3711	0.3664	−0.0313	0.031*
H16B	−0.2677	0.4320	0.0148	0.031*
C17	−0.32031 (15)	0.28178 (18)	0.05861 (9)	0.0275 (4)
H17A	−0.3604	0.2052	0.0435	0.033*
H17B	−0.3651	0.3324	0.0804	0.033*
C18	−0.21338 (14)	0.25052 (16)	0.10695 (8)	0.0207 (4)
H18A	−0.1765	0.3273	0.1251	0.025*
H18B	−0.2281	0.2024	0.1433	0.025*
C19	0.00103 (13)	0.50061 (15)	0.16902 (8)	0.0170 (3)
C20	0.00121 (17)	0.55092 (16)	0.10254 (9)	0.0251 (4)
H20A	0.0599	0.5127	0.0874	0.038*
H20B	0.0121	0.6399	0.1054	0.038*
H20C	−0.0682	0.5326	0.0719	0.038*
C21	0.79125 (14)	0.81068 (15)	0.18393 (8)	0.0184 (4)
H21A	0.7770	0.7760	0.2245	0.022*
C22	0.73229 (14)	0.73242 (16)	0.12695 (8)	0.0224 (4)
H22A	0.7564	0.6462	0.1344	0.027*
H22B	0.7505	0.7613	0.0869	0.027*
C23	0.61009 (15)	0.73912 (18)	0.11812 (9)	0.0284 (4)
H23A	0.5911	0.6999	0.1558	0.034*
H23B	0.5736	0.6929	0.0787	0.034*
C24	0.56931 (16)	0.87123 (19)	0.11199 (10)	0.0323 (5)
H24A	0.5791	0.9072	0.0711	0.039*
H24B	0.4911	0.8723	0.1102	0.039*
C25	0.63031 (15)	0.94796 (19)	0.16928 (10)	0.0302 (4)
H25A	0.6056	1.0342	0.1629	0.036*
H25B	0.6137	0.9174	0.2095	0.036*
C26	0.75158 (15)	0.94279 (16)	0.17677 (9)	0.0242 (4)
H26A	0.7890	0.9905	0.2155	0.029*
H26B	0.7691	0.9802	0.1383	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0168 (2)	0.0128 (2)	0.0132 (2)	0.00017 (16)	0.00465 (16)	0.00000 (15)
O1	0.0194 (6)	0.0131 (6)	0.0164 (6)	−0.0014 (4)	0.0051 (5)	−0.0006 (4)
O2	0.0365 (8)	0.0165 (6)	0.0221 (6)	0.0046 (5)	0.0157 (6)	0.0018 (5)
O3	0.0317 (7)	0.0137 (6)	0.0225 (6)	0.0031 (5)	0.0068 (5)	0.0004 (5)
N1	0.0182 (7)	0.0144 (7)	0.0153 (7)	−0.0001 (6)	0.0030 (6)	−0.0026 (5)
N2	0.0176 (7)	0.0156 (7)	0.0131 (7)	−0.0019 (5)	0.0043 (6)	−0.0006 (5)
N3	0.0193 (7)	0.0189 (7)	0.0140 (7)	0.0030 (6)	0.0068 (6)	0.0000 (6)
N4	0.0215 (8)	0.0137 (7)	0.0184 (7)	0.0004 (6)	0.0071 (6)	0.0008 (6)
C1	0.0167 (8)	0.0169 (8)	0.0168 (8)	0.0018 (6)	0.0060 (7)	0.0011 (6)
C2	0.0246 (9)	0.0192 (9)	0.0220 (9)	0.0002 (7)	0.0036 (7)	0.0040 (7)
C3	0.0324 (11)	0.0225 (10)	0.0272 (10)	0.0075 (8)	0.0056 (8)	0.0055 (8)
C4	0.0250 (10)	0.0378 (11)	0.0216 (9)	0.0108 (8)	0.0073 (8)	0.0062 (8)
C5	0.0204 (9)	0.0377 (11)	0.0245 (10)	0.0018 (8)	0.0025 (8)	−0.0001 (8)
C6	0.0234 (9)	0.0258 (10)	0.0205 (9)	−0.0006 (8)	0.0032 (7)	−0.0031 (7)
C7	0.0168 (8)	0.0140 (8)	0.0159 (8)	−0.0015 (6)	0.0039 (6)	−0.0010 (6)
C8	0.0187 (9)	0.0157 (8)	0.0238 (9)	0.0004 (7)	0.0064 (7)	−0.0004 (7)
C9	0.0189 (9)	0.0248 (10)	0.0355 (11)	−0.0012 (7)	0.0081 (8)	−0.0027 (8)
C10	0.0242 (10)	0.0206 (9)	0.0317 (10)	−0.0073 (7)	0.0095 (8)	−0.0035 (8)
C11	0.0302 (10)	0.0162 (9)	0.0285 (10)	−0.0021 (7)	0.0107 (8)	−0.0015 (7)
C12	0.0233 (9)	0.0147 (8)	0.0266 (9)	0.0015 (7)	0.0106 (8)	0.0019 (7)
C13	0.0180 (8)	0.0137 (8)	0.0179 (8)	0.0004 (6)	0.0046 (7)	−0.0001 (6)
C14	0.0205 (9)	0.0163 (8)	0.0183 (8)	0.0003 (7)	0.0061 (7)	−0.0006 (7)
C15	0.0273 (10)	0.0194 (9)	0.0198 (9)	−0.0017 (7)	0.0033 (7)	0.0028 (7)
C16	0.0213 (9)	0.0260 (10)	0.0284 (10)	0.0053 (7)	0.0040 (8)	0.0063 (8)
C17	0.0209 (10)	0.0301 (11)	0.0335 (10)	0.0042 (8)	0.0106 (8)	0.0064 (8)
C18	0.0224 (9)	0.0189 (9)	0.0231 (9)	0.0012 (7)	0.0103 (7)	0.0021 (7)
C19	0.0187 (8)	0.0143 (8)	0.0182 (8)	−0.0031 (6)	0.0050 (7)	−0.0007 (6)
C20	0.0401 (11)	0.0169 (9)	0.0217 (9)	0.0004 (8)	0.0141 (8)	0.0000 (7)
C21	0.0196 (9)	0.0168 (8)	0.0198 (8)	−0.0005 (7)	0.0069 (7)	0.0013 (6)
C22	0.0264 (10)	0.0196 (9)	0.0209 (9)	−0.0018 (7)	0.0056 (7)	0.0009 (7)
C23	0.0238 (10)	0.0326 (11)	0.0269 (10)	−0.0040 (8)	0.0031 (8)	0.0006 (8)
C24	0.0228 (10)	0.0390 (12)	0.0334 (11)	0.0046 (8)	0.0041 (8)	0.0048 (9)
C25	0.0251 (10)	0.0309 (11)	0.0349 (11)	0.0075 (8)	0.0080 (8)	0.0002 (8)
C26	0.0268 (10)	0.0185 (9)	0.0280 (10)	0.0029 (7)	0.0079 (8)	−0.0001 (7)

Geometric parameters (Å, º) top

P1—O1	1.4964 (12)	C10—H10B	0.9900
P1—N3	1.6315 (14)	C11—C12	1.524 (2)
P1—N2	1.6440 (14)	C11—H11A	0.9900
P1—N1	1.6463 (14)	C11—H11B	0.9900
O2—C19	1.260 (2)	C12—H12A	0.9900
O3—C19	1.250 (2)	C12—H12B	0.9900
N1—C13	1.467 (2)	C13—C18	1.519 (2)
N1—H1N	0.857 (14)	C13—C14	1.530 (2)
N2—C7	1.466 (2)	C13—H13A	1.0000
N2—H2N	0.868 (14)	C14—C15	1.521 (2)
N3—C1	1.467 (2)	C14—H14A	0.9900
N3—H3N	0.841 (14)	C14—H14B	0.9900
N4—C21	1.484 (2)	C15—C16	1.521 (3)
N4—H4NC	0.894 (14)	C15—H15A	0.9900
N4—H4NB	0.888 (15)	C15—H15B	0.9900
N4—H4NA	0.879 (15)	C16—C17	1.525 (3)
C1—C6	1.520 (2)	C16—H16A	0.9900
C1—C2	1.527 (2)	C16—H16B	0.9900
C1—H1A	1.0000	C17—C18	1.527 (3)
C2—C3	1.529 (3)	C17—H17A	0.9900
C2—H2B	0.9900	C17—H17B	0.9900
C2—H2A	0.9900	C18—H18A	0.9900
C3—C4	1.521 (3)	C18—H18B	0.9900
C3—H3B	0.9900	C19—C20	1.518 (2)
C3—H3A	0.9900	C20—H20A	0.9800
C4—C5	1.519 (3)	C20—H20B	0.9800
C4—H4A	0.9900	C20—H20C	0.9800
C4—H4B	0.9900	C21—C22	1.519 (2)
C5—C6	1.525 (3)	C21—C26	1.521 (2)
C5—H5A	0.9900	C21—H21A	1.0000
C5—H5B	0.9900	C22—C23	1.526 (3)
C6—H6A	0.9900	C22—H22A	0.9900
C6—H6B	0.9900	C22—H22B	0.9900
C7—C8	1.519 (2)	C23—C24	1.526 (3)
C7—C12	1.528 (2)	C23—H23A	0.9900
C7—H7A	1.0000	C23—H23B	0.9900
C8—C9	1.527 (2)	C24—C25	1.522 (3)
C8—H8A	0.9900	C24—H24A	0.9900
C8—H8B	0.9900	C24—H24B	0.9900
C9—C10	1.525 (3)	C25—C26	1.517 (3)
C9—H9A	0.9900	C25—H25A	0.9900
C9—H9B	0.9900	C25—H25B	0.9900
C10—C11	1.520 (2)	C26—H26A	0.9900
C10—H10A	0.9900	C26—H26B	0.9900

O1—P1—N3	118.96 (7)	C11—C12—C7	109.97 (14)
O1—P1—N2	108.44 (7)	C11—C12—H12A	109.7
N3—P1—N2	103.05 (7)	C7—C12—H12A	109.7
O1—P1—N1	107.84 (7)	C11—C12—H12B	109.7
N3—P1—N1	101.99 (7)	C7—C12—H12B	109.7
N2—P1—N1	116.95 (7)	H12A—C12—H12B	108.2
C13—N1—P1	120.26 (11)	N1—C13—C18	109.44 (13)
C13—N1—H1N	114.0 (13)	N1—C13—C14	113.53 (13)
P1—N1—H1N	115.0 (13)	C18—C13—C14	110.69 (14)
C7—N2—P1	123.78 (11)	N1—C13—H13A	107.7
C7—N2—H2N	115.0 (12)	C18—C13—H13A	107.7
P1—N2—H2N	114.7 (12)	C14—C13—H13A	107.7
C1—N3—P1	123.63 (11)	C15—C14—C13	111.59 (14)
C1—N3—H3N	117.3 (13)	C15—C14—H14A	109.3
P1—N3—H3N	116.0 (13)	C13—C14—H14A	109.3
C21—N4—H4NC	111.1 (12)	C15—C14—H14B	109.3
C21—N4—H4NB	110.3 (12)	C13—C14—H14B	109.3
H4NC—N4—H4NB	111.7 (18)	H14A—C14—H14B	108.0
C21—N4—H4NA	110.9 (13)	C14—C15—C16	111.84 (15)
H4NC—N4—H4NA	108.0 (17)	C14—C15—H15A	109.2
H4NB—N4—H4NA	104.6 (18)	C16—C15—H15A	109.2
N3—C1—C6	110.51 (14)	C14—C15—H15B	109.2
N3—C1—C2	113.85 (14)	C16—C15—H15B	109.2
C6—C1—C2	110.19 (14)	H15A—C15—H15B	107.9
N3—C1—H1A	107.3	C15—C16—C17	110.59 (15)
C6—C1—H1A	107.3	C15—C16—H16A	109.5
C2—C1—H1A	107.3	C17—C16—H16A	109.5
C1—C2—C3	109.95 (15)	C15—C16—H16B	109.5
C1—C2—H2B	109.7	C17—C16—H16B	109.5
C3—C2—H2B	109.7	H16A—C16—H16B	108.1
C1—C2—H2A	109.7	C16—C17—C18	111.06 (15)
C3—C2—H2A	109.7	C16—C17—H17A	109.4
H2B—C2—H2A	108.2	C18—C17—H17A	109.4
C4—C3—C2	112.27 (16)	C16—C17—H17B	109.4
C4—C3—H3B	109.2	C18—C17—H17B	109.4
C2—C3—H3B	109.2	H17A—C17—H17B	108.0
C4—C3—H3A	109.2	C13—C18—C17	111.40 (15)
C2—C3—H3A	109.2	C13—C18—H18A	109.3
H3B—C3—H3A	107.9	C17—C18—H18A	109.3
C5—C4—C3	111.49 (15)	C13—C18—H18B	109.3
C5—C4—H4A	109.3	C17—C18—H18B	109.3
C3—C4—H4A	109.3	H18A—C18—H18B	108.0
C5—C4—H4B	109.3	O3—C19—O2	124.04 (15)
C3—C4—H4B	109.3	O3—C19—C20	118.69 (15)
H4A—C4—H4B	108.0	O2—C19—C20	117.26 (15)
C4—C5—C6	111.38 (16)	C19—C20—H20A	109.5
C4—C5—H5A	109.4	C19—C20—H20B	109.5
C6—C5—H5A	109.4	H20A—C20—H20B	109.5
C4—C5—H5B	109.4	C19—C20—H20C	109.5
C6—C5—H5B	109.4	H20A—C20—H20C	109.5
H5A—C5—H5B	108.0	H20B—C20—H20C	109.5
C1—C6—C5	110.73 (15)	N4—C21—C22	110.56 (14)
C1—C6—H6A	109.5	N4—C21—C26	109.43 (14)
C5—C6—H6A	109.5	C22—C21—C26	111.46 (15)
C1—C6—H6B	109.5	N4—C21—H21A	108.4
C5—C6—H6B	109.5	C22—C21—H21A	108.4
H6A—C6—H6B	108.1	C26—C21—H21A	108.4
N2—C7—C8	109.29 (13)	C21—C22—C23	110.98 (15)
N2—C7—C12	114.46 (14)	C21—C22—H22A	109.4
C8—C7—C12	110.43 (13)	C23—C22—H22A	109.4
N2—C7—H7A	107.5	C21—C22—H22B	109.4
C8—C7—H7A	107.5	C23—C22—H22B	109.4
C12—C7—H7A	107.5	H22A—C22—H22B	108.0
C7—C8—C9	111.62 (14)	C22—C23—C24	111.85 (16)
C7—C8—H8A	109.3	C22—C23—H23A	109.2
C9—C8—H8A	109.3	C24—C23—H23A	109.2
C7—C8—H8B	109.3	C22—C23—H23B	109.2
C9—C8—H8B	109.3	C24—C23—H23B	109.2
H8A—C8—H8B	108.0	H23A—C23—H23B	107.9
C10—C9—C8	111.84 (15)	C25—C24—C23	110.81 (16)
C10—C9—H9A	109.2	C25—C24—H24A	109.5
C8—C9—H9A	109.2	C23—C24—H24A	109.5
C10—C9—H9B	109.2	C25—C24—H24B	109.5
C8—C9—H9B	109.2	C23—C24—H24B	109.5
H9A—C9—H9B	107.9	H24A—C24—H24B	108.1
C11—C10—C9	111.14 (15)	C26—C25—C24	111.55 (16)
C11—C10—H10A	109.4	C26—C25—H25A	109.3
C9—C10—H10A	109.4	C24—C25—H25A	109.3
C11—C10—H10B	109.4	C26—C25—H25B	109.3
C9—C10—H10B	109.4	C24—C25—H25B	109.3
H10A—C10—H10B	108.0	H25A—C25—H25B	108.0
C10—C11—C12	111.37 (15)	C25—C26—C21	110.54 (15)
C10—C11—H11A	109.4	C25—C26—H26A	109.5
C12—C11—H11A	109.4	C21—C26—H26A	109.5
C10—C11—H11B	109.4	C25—C26—H26B	109.5
C12—C11—H11B	109.4	C21—C26—H26B	109.5
H11A—C11—H11B	108.0	H26A—C26—H26B	108.1

O1—P1—N1—C13	−39.88 (14)	C8—C9—C10—C11	53.0 (2)
N3—P1—N1—C13	−165.92 (12)	C9—C10—C11—C12	−55.6 (2)
N2—P1—N1—C13	82.56 (14)	C10—C11—C12—C7	58.17 (19)
O1—P1—N2—C7	−172.79 (12)	N2—C7—C12—C11	178.05 (14)
N3—P1—N2—C7	−45.84 (14)	C8—C7—C12—C11	−58.12 (18)
N1—P1—N2—C7	65.08 (15)	P1—N1—C13—C18	160.06 (12)
O1—P1—N3—C1	75.27 (15)	P1—N1—C13—C14	−75.72 (16)
N2—P1—N3—C1	−44.69 (14)	N1—C13—C14—C15	−178.14 (13)
N1—P1—N3—C1	−166.34 (13)	C18—C13—C14—C15	−54.60 (19)
P1—N3—C1—C6	148.80 (13)	C13—C14—C15—C16	54.91 (19)
P1—N3—C1—C2	−86.58 (17)	C14—C15—C16—C17	−55.3 (2)
N3—C1—C2—C3	177.23 (14)	C15—C16—C17—C18	55.9 (2)
C6—C1—C2—C3	−57.97 (18)	N1—C13—C18—C17	−178.57 (14)
C1—C2—C3—C4	55.5 (2)	C14—C13—C18—C17	55.56 (19)
C2—C3—C4—C5	−53.4 (2)	C16—C17—C18—C13	−56.7 (2)
C3—C4—C5—C6	53.4 (2)	N4—C21—C22—C23	−177.38 (14)
N3—C1—C6—C5	−174.36 (14)	C26—C21—C22—C23	−55.43 (19)
C2—C1—C6—C5	58.95 (19)	C21—C22—C23—C24	54.4 (2)
C4—C5—C6—C1	−56.6 (2)	C22—C23—C24—C25	−54.3 (2)
P1—N2—C7—C8	152.71 (12)	C23—C24—C25—C26	55.5 (2)
P1—N2—C7—C12	−82.85 (17)	C24—C25—C26—C21	−56.7 (2)
N2—C7—C8—C9	−177.01 (14)	N4—C21—C26—C25	179.20 (14)
C12—C7—C8—C9	56.22 (19)	C22—C21—C26—C25	56.6 (2)
C7—C8—C9—C10	−53.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.87 (1)	2.14 (2)	3.0049 (18)	171 (2)
N3—H3N···O2ⁱⁱ	0.84 (1)	2.05 (2)	2.8837 (18)	173 (2)
N1—H1N···O3	0.86 (1)	2.21 (2)	3.0394 (18)	163 (2)
N4—H4NC···O1ⁱⁱⁱ	0.89 (1)	2.05 (2)	2.9445 (18)	178 (2)
N4—H4NB···O3^iv	0.89 (2)	1.94 (2)	2.7666 (19)	155 (2)
N4—H4NA···O2^v	0.88 (2)	1.83 (2)	2.6992 (19)	169 (2)

Symmetry codes: (i) −x, −y, −z; (ii) −x, y−1/2, −z+1/2; (iii) x+1, y+1, z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₆H₁₄N⁺·C₂H₃O₂⁻·C₁₈H₃₆N₃OP
M_r	500.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	90
a, b, c (Å)	12.7663 (8), 10.9011 (7), 21.2791 (13)
β (°)	104.523 (3)
V (Å³)	2866.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.35 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.957, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	21979, 5898, 4702
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 0.97
No. of reflections	5898
No. of parameters	326
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.47

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.868 (14)	2.144 (15)	3.0049 (18)	171.3 (17)
N3—H3N···O2ⁱⁱ	0.841 (14)	2.047 (15)	2.8837 (18)	173.3 (19)
N1—H1N···O3	0.857 (14)	2.209 (15)	3.0394 (18)	163.3 (18)
N4—H4NC···O1ⁱⁱⁱ	0.894 (14)	2.051 (15)	2.9445 (18)	178.2 (18)
N4—H4NB···O3^iv	0.888 (15)	1.935 (16)	2.7666 (19)	155.2 (17)
N4—H4NA···O2^v	0.879 (15)	1.831 (15)	2.6992 (19)	168.9 (18)

Symmetry codes: (i) −x, −y, −z; (ii) −x, y−1/2, −z+1/2; (iii) x+1, y+1, z; (iv) −x+1, y+1/2, −z+1/2; (v) x+1, y, z.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Nečas, M. & Negari, M. (2012). Acta Cryst. C68, o51–o56. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Tarahhomi, A., Karimi Ahmadabad, F., Fejfarová, K., Lee, A. van der & Dušek, M. (2012). Acta Cryst. C68, o164–o169. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sabbaghi, F., Pourayoubi, M., Karimi Ahmadabad, F., Azarkamanzad, Z. & Ebrahimi Valmoozi, A. A. (2011). Acta Cryst. E67, o502. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vollhardt, K. P. C. & Schore, N. E. (1998). Organic Chemistry: Structure and Function, 3rd ed., ch. 19, p. 837. New York: W. H. Freeman Co. Google Scholar

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

Cyclo­hexyl­ammonium acetate–N,N′,N′′-tri­cyclo­hexyl­phospho­ric tri­amide (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Cyclohexylammonium acetate–N,N′,N′′-tricyclohexylphosphoric triamide (1/1)