N,N-Dimethyl-N′,N′′-bis­(2-methyl­phenyl)phospho­ric triamide mono­hydrate

Eslami, F.; Pourayoubi, M.; Yousefi, M.; Rheingold, A.L.; Golen, J.A.

doi:10.1107/S1600536812033995

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2650

doi:10.1107/S1600536812033995

Open

access

N,N-Dimethyl-N′,N′′-bis(2-methylphenyl)phosphoric triamide monohydrate

Farnaz Eslami,^a Mehrdad Pourayoubi,^b ^* Mohammad Yousefi,^a Arnold L. Rheingold ^c and James A. Golen ^c

^aDepartment of Chemistry, Shahr-e Rey Branch, Islamic Azad University, Tehran, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, CA 92093, USA
^*Correspondence e-mail: pourayoubi@um.ac.ir

(Received 13 July 2012; accepted 30 July 2012; online 4 August 2012)

In the title compound, C₁₆H₂₂N₃OP·H₂O, the P atom adopts a distorted tetrahedral environment with the bond angles around the P atom in the range 99.98 (7)–116.20 (7)°. The P—N bond length in the [(CH₃)₂N]P(O) fragment [1.6392 (14) Å] is slightly shorter than two other P—N bonds [1.6439 (15) and 1.6530 (14) Å]. In the (CH₃)₂NP(O) fragment, one of the methyl groups is syn to the P=O bond, whereas the other one is anti to the P=O bond [C—N—P=O torsion angles = 4.80 (17) and −174.57 (15)°]. In the crystal, the water molecules form hydrogen bonds to the O atoms of the P=O bond of two different molecules and act as acceptors for the two amino H atoms of the same molecule. As a result, chains parallel to [010] are formed.

Related literature

For phosphoramidates having a [(CH₃)₂N]P(O) fragment and for P=O and P—N bond lengths, see: Pourayoubi, Tarahhomi et al. (2012 ); Pourayoubi et al. (2011 ). For the double H-atom acceptor capability of the P=O group, see: Pourayoubi, Nečas & Negari (2012 ).

Experimental

Crystal data

C₁₆H₂₂N₃OP·H₂O
M_r = 321.35
Monoclinic, P 2₁ /n
a = 10.7058 (16) Å
b = 7.2541 (11) Å
c = 22.091 (3) Å
β = 90.971 (2)°
V = 1715.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 100 K
0.20 × 0.14 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.967, T_max = 0.977
15201 measured reflections
4036 independent reflections
3135 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.115
S = 1.04
4036 reflections
215 parameters
5 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H2W⋯O1ⁱ	0.84 (1)	1.91 (2)	2.7491 (17)	173 (2)
O1W—H1W⋯O1ⁱⁱ	0.85 (1)	1.91 (1)	2.7607 (17)	175 (2)
N1—H1N⋯O1W	0.87 (1)	2.04 (2)	2.8724 (19)	159 (2)
N2—H2N⋯O1W	0.87 (1)	2.00 (2)	2.8473 (18)	164 (2)
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812033995/bt5974sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033995/bt5974Isup2.hkl

checkCIF report

Comment top

The crystal structure determination of the title hydrate phosphoric triamide (Fig. 1) was performed as a part of work on synthesis and X-ray crystallography of compounds with a [(CH₃)₂N]P(O) fragment (Pourayoubi, Tarahhomi et al., 2012; Pourayoubi et al., 2011).

In the phosphoric triamide molecule, the P atom adopts a distorted (N)P(O)(N)₂ tetrahedral environment. The P═O and P—N bond lengths are within the expected values (Pourayoubi, Tarahhomi et al., 2012; Pourayoubi et al., 2011). The sum of three bond angles at the nitrogen atom of the dimethylamido fragment, C11—N3—C10 + C11—N3—P1 + C10—N3—P1, of 360° suggests sp² hybridization for this N atom. Moreover, the C6—N1—P1 and C4—N2—P1 bond angles are 125.07 (12)° and 125.66 (12)°, respectively. The P—N bond length of the [(CH₃)₂N]P(O) fragment is shorter than two other P—N bonds.

In the crystal, the oxygen atoms of phosphoryl group and water molecule act as double-hydrogen bond acceptors (for a definition of double-hydrogen bond acceptor, see: Pourayoubi, Nečas & Negari, 2012) to form O—H···O···H—O and N—H···O···H—N groups. The phosphoric triamide and water molecules are aggregated through these hydrogen bonds in a linear arrangement parallel to the b axis, Fig. 2.

Related literature top

For phosphoramidates having a [(CH₃)₂N]P(O) fragment and for P═O and P—N bond lengths, see: Pourayoubi, Tarahhomi et al. (2012); Pourayoubi et al. (2011). For the double H-atom acceptability of the P=O group, see: Pourayoubi, Nečas & Negari (2012).

Experimental top

Synthesis of ((CH₃)₂N)P(O)Cl₂: [(CH₃)₂NH₂]Cl (0.184 mol) and P(O)Cl₃ (0.552 mol) were refluxed for 8 h and afterwards the excess of P(O)Cl₃ was removed in vacuo.

Synthesis of title compound: To a solution of ((CH₃)₂N)P(O)Cl₂ (3.7 mmol) in CHCl₃ (15 ml), a solution of ortho-toluidine (14.8 mmol) in the same solvent (25 ml) was added at 273 K. After 4 h stirring, the solvent was removed and product was washed with deionized water and recrystallized from chloroform/n-hexene at room temperature to yield colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. An ORTEP-style plot and atom labeling scheme for the title hydrate compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. Packing in the title compound with hydrogen bonds shown as dotted lines. Only H atoms involved in hydrogen bonds are shown.

N,N-Dimethyl-N',N''-bis(2-methylphenyl)phosphoric triamide monohydrate top

Crystal data top

C₁₆H₂₂N₃OP·H₂O	F(000) = 688
M_r = 321.35	D_x = 1.244 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4384 reflections
a = 10.7058 (16) Å	θ = 3.0–28.1°
b = 7.2541 (11) Å	µ = 0.17 mm⁻¹
c = 22.091 (3) Å	T = 100 K
β = 90.971 (2)°	Block, colourless
V = 1715.3 (4) Å³	0.20 × 0.14 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	4036 independent reflections
Radiation source: fine-focus sealed tube	3135 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −14→13
T_min = 0.967, T_max = 0.977	k = −9→9
15201 measured reflections	l = −29→29

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0495P)² + 0.3428P] where P = (F_o² + 2F_c²)/3
4036 reflections	(Δ/σ)_max < 0.001
215 parameters	Δρ_max = 0.30 e Å⁻³
5 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₂₂N₃OP·H₂O	V = 1715.3 (4) Å³
M_r = 321.35	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7058 (16) Å	µ = 0.17 mm⁻¹
b = 7.2541 (11) Å	T = 100 K
c = 22.091 (3) Å	0.20 × 0.14 × 0.14 mm
β = 90.971 (2)°

Data collection top

Bruker APEXII CCD diffractometer	4036 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	3135 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.977	R_int = 0.050
15201 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	5 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
4036 reflections	Δρ_min = −0.38 e Å⁻³
215 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	0.30253 (4)	0.63760 (6)	0.045212 (19)	0.02129 (13)
O1W	0.43897 (12)	0.18044 (16)	0.04084 (6)	0.0283 (3)
H1W	0.5043 (15)	0.175 (3)	0.0196 (8)	0.034*
H2W	0.4105 (16)	0.072 (2)	0.0412 (8)	0.034*
N1	0.31522 (13)	0.49375 (19)	−0.01239 (6)	0.0235 (3)
H1N	0.3457 (17)	0.385 (2)	−0.0046 (8)	0.028*
O1	0.35590 (11)	0.82247 (16)	0.03322 (5)	0.0273 (3)
N3	0.15544 (13)	0.6646 (2)	0.06265 (7)	0.0273 (3)
C1	0.39835 (17)	0.6608 (3)	0.28289 (8)	0.0336 (4)
H1	0.4026	0.6910	0.3247	0.040*
C2	0.35064 (16)	0.7858 (3)	0.24143 (8)	0.0314 (4)
H2	0.3230	0.9034	0.2545	0.038*
C3	0.34322 (16)	0.7391 (2)	0.18036 (8)	0.0281 (4)
H3	0.3109	0.8255	0.1518	0.034*
C4	0.38270 (15)	0.5666 (2)	0.16075 (7)	0.0233 (3)
N2	0.37225 (13)	0.5161 (2)	0.09875 (6)	0.0243 (3)
H2N	0.4025 (17)	0.411 (2)	0.0871 (8)	0.029*
C6	0.26974 (15)	0.5277 (2)	−0.07211 (7)	0.0232 (3)
C7	0.27217 (15)	0.3843 (2)	−0.11509 (8)	0.0259 (4)
C8	0.22525 (16)	0.4208 (3)	−0.17281 (8)	0.0312 (4)
H8	0.2260	0.3251	−0.2022	0.037*
C9	0.17722 (16)	0.5919 (3)	−0.18920 (8)	0.0327 (4)
H9	0.1445	0.6125	−0.2289	0.039*
C10	0.08215 (18)	0.5071 (3)	0.08193 (10)	0.0458 (5)
H10A	0.0604	0.5220	0.1246	0.069*
H10B	0.1311	0.3941	0.0771	0.069*
H10C	0.0055	0.4992	0.0572	0.069*
C11	0.09013 (19)	0.8401 (3)	0.06091 (9)	0.0403 (5)
H11A	0.0206	0.8333	0.0316	0.060*
H11B	0.1480	0.9376	0.0488	0.060*
H11C	0.0578	0.8679	0.1011	0.060*
C12	0.22373 (16)	0.7000 (2)	−0.08851 (8)	0.0266 (4)
H12	0.2236	0.7970	−0.0596	0.032*
C13	0.17799 (16)	0.7313 (3)	−0.14671 (8)	0.0309 (4)
H13	0.1469	0.8498	−0.1574	0.037*
C14	0.32410 (18)	0.1973 (3)	−0.09952 (8)	0.0336 (4)
H14A	0.3166	0.1163	−0.1349	0.050*
H14B	0.2773	0.1445	−0.0660	0.050*
H14C	0.4123	0.2091	−0.0876	0.050*
C15	0.43306 (15)	0.4396 (2)	0.20245 (8)	0.0257 (4)
C16	0.47558 (18)	0.2518 (3)	0.18325 (8)	0.0330 (4)
H16A	0.5079	0.1843	0.2186	0.050*
H16B	0.5417	0.2642	0.1534	0.050*
H16C	0.4049	0.1843	0.1652	0.050*
C17	0.43986 (16)	0.4911 (3)	0.26294 (8)	0.0322 (4)
H17	0.4742	0.4069	0.2916	0.039*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0220 (2)	0.0178 (2)	0.0242 (2)	−0.00113 (16)	0.00295 (16)	−0.00023 (16)
O1W	0.0330 (7)	0.0177 (6)	0.0344 (7)	−0.0005 (5)	0.0081 (5)	−0.0033 (5)
N1	0.0295 (8)	0.0169 (7)	0.0240 (7)	0.0007 (6)	0.0004 (6)	0.0001 (6)
O1	0.0294 (6)	0.0196 (6)	0.0330 (6)	−0.0041 (5)	0.0035 (5)	−0.0014 (5)
N3	0.0232 (7)	0.0259 (8)	0.0331 (8)	0.0014 (6)	0.0046 (6)	0.0030 (6)
C1	0.0321 (10)	0.0433 (11)	0.0252 (9)	−0.0036 (8)	−0.0006 (7)	−0.0073 (8)
C2	0.0260 (9)	0.0334 (10)	0.0347 (10)	−0.0008 (8)	0.0012 (7)	−0.0109 (8)
C3	0.0281 (9)	0.0268 (9)	0.0293 (9)	0.0019 (7)	−0.0020 (7)	−0.0030 (7)
C4	0.0206 (8)	0.0248 (9)	0.0244 (8)	−0.0026 (7)	0.0011 (6)	−0.0020 (7)
N2	0.0283 (7)	0.0203 (7)	0.0244 (7)	0.0022 (6)	0.0012 (6)	−0.0042 (6)
C6	0.0209 (8)	0.0245 (9)	0.0242 (8)	−0.0050 (6)	0.0022 (6)	0.0004 (7)
C7	0.0227 (8)	0.0264 (9)	0.0287 (9)	−0.0049 (7)	0.0037 (7)	−0.0035 (7)
C8	0.0286 (9)	0.0384 (11)	0.0267 (9)	−0.0056 (8)	0.0025 (7)	−0.0057 (8)
C9	0.0270 (9)	0.0453 (12)	0.0258 (9)	−0.0048 (8)	−0.0017 (7)	0.0039 (8)
C10	0.0289 (10)	0.0475 (13)	0.0613 (14)	−0.0055 (9)	0.0109 (9)	0.0170 (11)
C11	0.0372 (11)	0.0417 (12)	0.0422 (11)	0.0157 (9)	0.0084 (9)	0.0062 (9)
C12	0.0268 (9)	0.0239 (9)	0.0293 (9)	−0.0037 (7)	−0.0001 (7)	−0.0001 (7)
C13	0.0278 (9)	0.0299 (10)	0.0350 (10)	−0.0041 (7)	−0.0007 (7)	0.0078 (8)
C14	0.0374 (10)	0.0297 (10)	0.0338 (10)	0.0008 (8)	−0.0007 (8)	−0.0085 (8)
C15	0.0202 (8)	0.0267 (9)	0.0302 (9)	−0.0030 (7)	0.0002 (7)	−0.0004 (7)
C16	0.0391 (10)	0.0288 (10)	0.0310 (9)	0.0033 (8)	−0.0018 (8)	0.0042 (7)
C17	0.0295 (9)	0.0391 (11)	0.0278 (9)	−0.0023 (8)	−0.0035 (7)	0.0006 (8)

Geometric parameters (Å, º) top

P1—O1	1.4833 (12)	C7—C14	1.504 (2)
P1—N3	1.6392 (14)	C8—C9	1.389 (3)
P1—N2	1.6439 (15)	C8—H8	0.9500
P1—N1	1.6530 (14)	C9—C13	1.380 (3)
O1W—H1W	0.850 (14)	C9—H9	0.9500
O1W—H2W	0.841 (14)	C10—H10A	0.9800
N1—C6	1.420 (2)	C10—H10B	0.9800
N1—H1N	0.871 (14)	C10—H10C	0.9800
N3—C11	1.453 (2)	C11—H11A	0.9800
N3—C10	1.454 (2)	C11—H11B	0.9800
C1—C2	1.381 (3)	C11—H11C	0.9800
C1—C17	1.383 (3)	C12—C13	1.387 (2)
C1—H1	0.9500	C12—H12	0.9500
C2—C3	1.392 (2)	C13—H13	0.9500
C2—H2	0.9500	C14—H14A	0.9800
C3—C4	1.392 (2)	C14—H14B	0.9800
C3—H3	0.9500	C14—H14C	0.9800
C4—C15	1.404 (2)	C15—C17	1.388 (2)
C4—N2	1.420 (2)	C15—C16	1.500 (2)
N2—H2N	0.869 (14)	C16—H16A	0.9800
C6—C12	1.389 (2)	C16—H16B	0.9800
C6—C7	1.409 (2)	C16—H16C	0.9800
C7—C8	1.388 (2)	C17—H17	0.9500

O1—P1—N3	107.97 (7)	C13—C9—H9	120.7
O1—P1—N2	116.20 (7)	C8—C9—H9	120.7
N3—P1—N2	108.73 (7)	N3—C10—H10A	109.5
O1—P1—N1	113.35 (7)	N3—C10—H10B	109.5
N3—P1—N1	110.37 (7)	H10A—C10—H10B	109.5
N2—P1—N1	99.98 (7)	N3—C10—H10C	109.5
H1W—O1W—H2W	105.3 (15)	H10A—C10—H10C	109.5
C6—N1—P1	125.07 (12)	H10B—C10—H10C	109.5
C6—N1—H1N	117.5 (12)	N3—C11—H11A	109.5
P1—N1—H1N	117.1 (12)	N3—C11—H11B	109.5
C11—N3—C10	115.75 (15)	H11A—C11—H11B	109.5
C11—N3—P1	124.21 (12)	N3—C11—H11C	109.5
C10—N3—P1	120.03 (12)	H11A—C11—H11C	109.5
C2—C1—C17	119.38 (17)	H11B—C11—H11C	109.5
C2—C1—H1	120.3	C13—C12—C6	120.50 (17)
C17—C1—H1	120.3	C13—C12—H12	119.8
C1—C2—C3	119.80 (17)	C6—C12—H12	119.8
C1—C2—H2	120.1	C9—C13—C12	120.55 (18)
C3—C2—H2	120.1	C9—C13—H13	119.7
C4—C3—C2	120.53 (17)	C12—C13—H13	119.7
C4—C3—H3	119.7	C7—C14—H14A	109.5
C2—C3—H3	119.7	C7—C14—H14B	109.5
C3—C4—C15	120.06 (15)	H14A—C14—H14B	109.5
C3—C4—N2	120.83 (15)	C7—C14—H14C	109.5
C15—C4—N2	119.11 (15)	H14A—C14—H14C	109.5
C4—N2—P1	125.66 (12)	H14B—C14—H14C	109.5
C4—N2—H2N	119.2 (12)	C17—C15—C4	117.90 (16)
P1—N2—H2N	115.1 (12)	C17—C15—C16	120.38 (16)
C12—C6—C7	119.93 (15)	C4—C15—C16	121.70 (15)
C12—C6—N1	120.84 (15)	C15—C16—H16A	109.5
C7—C6—N1	119.23 (15)	C15—C16—H16B	109.5
C8—C7—C6	117.91 (17)	H16A—C16—H16B	109.5
C8—C7—C14	120.57 (16)	C15—C16—H16C	109.5
C6—C7—C14	121.52 (15)	H16A—C16—H16C	109.5
C7—C8—C9	122.43 (17)	H16B—C16—H16C	109.5
C7—C8—H8	118.8	C1—C17—C15	122.30 (18)
C9—C8—H8	118.8	C1—C17—H17	118.8
C13—C9—C8	118.67 (17)	C15—C17—H17	118.8

O1—P1—N1—C6	−55.73 (15)	P1—N1—C6—C7	−171.82 (12)
N3—P1—N1—C6	65.52 (15)	C12—C6—C7—C8	−1.3 (2)
N2—P1—N1—C6	179.92 (13)	N1—C6—C7—C8	178.99 (14)
O1—P1—N3—C11	4.80 (17)	C12—C6—C7—C14	178.50 (16)
N2—P1—N3—C11	131.68 (15)	N1—C6—C7—C14	−1.2 (2)
N1—P1—N3—C11	−119.60 (15)	C6—C7—C8—C9	0.3 (2)
O1—P1—N3—C10	−174.57 (15)	C14—C7—C8—C9	−179.55 (16)
N2—P1—N3—C10	−47.69 (17)	C7—C8—C9—C13	1.0 (3)
N1—P1—N3—C10	61.04 (16)	C7—C6—C12—C13	1.1 (2)
C17—C1—C2—C3	0.9 (3)	N1—C6—C12—C13	−179.17 (15)
C1—C2—C3—C4	0.5 (3)	C8—C9—C13—C12	−1.2 (3)
C2—C3—C4—C15	−1.4 (2)	C6—C12—C13—C9	0.1 (3)
C2—C3—C4—N2	178.28 (15)	C3—C4—C15—C17	1.0 (2)
C3—C4—N2—P1	−6.6 (2)	N2—C4—C15—C17	−178.72 (14)
C15—C4—N2—P1	173.12 (12)	C3—C4—C15—C16	179.43 (16)
O1—P1—N2—C4	61.98 (15)	N2—C4—C15—C16	−0.2 (2)
N3—P1—N2—C4	−60.03 (15)	C2—C1—C17—C15	−1.3 (3)
N1—P1—N2—C4	−175.68 (13)	C4—C15—C17—C1	0.4 (3)
P1—N1—C6—C12	8.5 (2)	C16—C15—C17—C1	−178.08 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H2W···O1ⁱ	0.84 (1)	1.91 (2)	2.7491 (17)	173 (2)
O1W—H1W···O1ⁱⁱ	0.85 (1)	1.91 (1)	2.7607 (17)	175 (2)
N1—H1N···O1W	0.87 (1)	2.04 (2)	2.8724 (19)	159 (2)
N2—H2N···O1W	0.87 (1)	2.00 (2)	2.8473 (18)	164 (2)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₂N₃OP·H₂O
M_r	321.35
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.7058 (16), 7.2541 (11), 22.091 (3)
β (°)	90.971 (2)
V (Å³)	1715.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.20 × 0.14 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.967, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	15201, 4036, 3135
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.115, 1.04
No. of reflections	4036
No. of parameters	215
No. of restraints	5
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXL97 (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
O1W—H2W···O1ⁱ	0.841 (14)	1.912 (15)	2.7491 (17)	173.2 (18)
O1W—H1W···O1ⁱⁱ	0.850 (14)	1.913 (14)	2.7607 (17)	174.9 (19)
N1—H1N···O1W	0.871 (14)	2.042 (15)	2.8724 (19)	159.1 (17)
N2—H2N···O1W	0.869 (14)	2.002 (15)	2.8473 (18)	163.9 (18)

Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z.

Acknowledgements

Support of this investigation by Shahr-e Rey Branch, Islamic Azad University, 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 CrossRef CAS IUCr Journals Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker Axs Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2008). SADABS. 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 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
Pourayoubi, M., Yousefi, M., Eslami, F., Rheingold, A. L. & Chen, C. (2011). Acta Cryst. E67, o3220. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar