Phenyl bis­(morpholin-4-yl­amido)­phosphinate

Pourayoubi, M.; Eshtiagh-Hosseini, H.; Negari, M.; Nečas, M.

doi:10.1107/S1600536811029734

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2202

doi:10.1107/S1600536811029734

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Phenyl bis(morpholin-4-ylamido)phosphinate

Mehrdad Pourayoubi,^a ^* Hossein Eshtiagh-Hosseini,^a Monireh Negari ^a and Marek Nečas ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 1 July 2011; accepted 22 July 2011; online 30 July 2011)

In the title compound, C₁₄H₂₃N₄O₄P, the P atom is in a distorted tetrahedral environment with bond angles in the range 96.87 (6)–119.86 (6)°. The two morpholinyl groups adopt a chair conformation. The phenyl ring is disordered over two sets of sites with equal occupancies [0.500 (2)]. In the crystal, adjacent molecules are linked via N—H⋯O hydrogen bonds into an extended chain running parallel to the a axis. Only one of the amidate N—H groups is involved in hydrogen bonding.

Related literature

For background to compounds having a P(=O)(O)(N)(N) skeleton, see: Sabbaghi et al. (2010 ). For bond lengths and angles in related structures, see: Ghadimi et al. (2009 ).

Experimental

Crystal data

C₁₄H₂₃N₄O₄P
M_r = 342.33
Triclinic, $[P \overline 1]$
a = 4.7469 (2) Å
b = 12.3528 (5) Å
c = 14.2149 (5) Å
α = 90.542 (3)°
β = 98.389 (4)°
γ = 93.009 (4)°
V = 823.35 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 120 K
0.20 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur S diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.877, T_max = 1.000
10043 measured reflections
2888 independent reflections
2272 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.070
S = 0.99
2888 reflections
262 parameters
162 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1ⁱ	0.823 (15)	2.093 (16)	2.8951 (16)	164.9 (15)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029734/gk2392sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029734/gk2392Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029734/gk2392Isup3.cml

checkCIF report

Comment top

Structure determination of the title compound, P(O)[OC₆H₅][NHNC₄H₈O]₂ (Fig. 1), was performed as a part of a project in our laboratory on the synthesis of compounds having a P(═O)(O)(N)(N) skeleton (Sabbaghi et al., 2010). Single crystals of title compound were obtained from a mixture of CH₃OH/CH₃CN (4:1 v/v) after slow evaporation at room temperature.

The P═O (1.4705 (10) Å), P—O (1.5975 (10) Å) and P—N (1.6295 (13) Å & 1.6331 (13) Å) bond lengths and the C—O—P angle (122.17 (8)°) are standard for this category of compounds (Ghadimi et al., 2009). The P atom has a distorted tetrahedral configuration (Fig. 1), the bond angles at the P atom vary in the range from 96.87 (6)° [the angle O2—P1—N3] to 119.86 (6)° [the angle O1—P1—N3].

In the crystal, the molecules are hydrogen-bonded in a linear arrangement parallel to [100] through N3—H3N···O1ⁱ [symmetry code: (i) x - 1, y, z] hydrogen bond (Table 1, Fig. 2).

Related literature top

For background to about compounds having a P(═O)(O)(N)(N) skeleton, see: Sabbaghi et al. (2010). For bond lengths in related structures, see: Ghadimi et al. (2009).

Experimental top

To a solution of phenyldichlorophosphate (2.507 mmol) in chloroform (15 ml), a solution of aminomorpholine (10.028 mmol) in chloroform (30 ml) was added at 273 K. After 4 h of stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals, suitable for crystallography, were obtained from a solution of the title compound in methanol and acetonitrile (4:1) after slow evaporation at room temperature. IR (KBr, cm^-1): 3278, 3107, 2945, 2869, 2830, 1588, 1488, 1223, 1107, 926, 869, 759, 698.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level. The disorder is not shown.
	Fig. 2. Partial packing view showing the formation of the chain through N—H···O hydrogen bond (shown as dotted lines). H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) x - 1, y, z]

N-[(morpholin-4-ylamino)(phenoxy)phosphoryl]morpholin-4-amine top

Crystal data top

C₁₄H₂₃N₄O₄P	Z = 2
M_r = 342.33	F(000) = 364
Triclinic, P1	D_x = 1.381 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7469 (2) Å	Cell parameters from 5042 reflections
b = 12.3528 (5) Å	θ = 3.3–27.2°
c = 14.2149 (5) Å	µ = 0.19 mm⁻¹
α = 90.542 (3)°	T = 120 K
β = 98.389 (4)°	Prism, colorless
γ = 93.009 (4)°	0.20 × 0.10 × 0.10 mm
V = 823.35 (6) Å³

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2888 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2272 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.3°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −14→14
T_min = 0.877, T_max = 1.000	l = −16→9
10043 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0404P)²P] where P = (F_o² + 2F_c²)/3
2888 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 0.22 e Å⁻³
162 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₂₃N₄O₄P	γ = 93.009 (4)°
M_r = 342.33	V = 823.35 (6) Å³
Triclinic, P1	Z = 2
a = 4.7469 (2) Å	Mo Kα radiation
b = 12.3528 (5) Å	µ = 0.19 mm⁻¹
c = 14.2149 (5) Å	T = 120 K
α = 90.542 (3)°	0.20 × 0.10 × 0.10 mm
β = 98.389 (4)°

Data collection top

Oxford Diffraction Xcalibur S diffractometer	2888 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2272 reflections with I > 2σ(I)
T_min = 0.877, T_max = 1.000	R_int = 0.021
10043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	162 restraints
wR(F²) = 0.070	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.22 e Å⁻³
2888 reflections	Δρ_min = −0.32 e Å⁻³
262 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	Occ. (<1)
P1	0.34183 (7)	0.63069 (3)	0.29935 (3)	0.01615 (12)
O1	0.55619 (19)	0.55524 (7)	0.33888 (7)	0.0196 (2)
O2	0.11776 (19)	0.58245 (7)	0.21233 (7)	0.0196 (3)
O3	0.1822 (2)	0.80213 (10)	0.63761 (8)	0.0382 (3)
O4	0.3795 (2)	1.01932 (8)	0.11186 (8)	0.0310 (3)
N3	0.1088 (3)	0.67116 (10)	0.36409 (9)	0.0180 (3)
C1	0.1500 (3)	0.48228 (11)	0.16832 (11)	0.0169 (3)
C2A	0.1144 (7)	0.3882 (2)	0.2144 (3)	0.0201 (8)	0.500 (2)
H2AA	0.0754	0.3896	0.2781	0.024*	0.500 (2)
C3A	0.1348 (8)	0.2902 (2)	0.1688 (3)	0.0228 (8)	0.500 (2)
H3AA	0.1112	0.2236	0.2004	0.027*	0.500 (2)
C4A	0.192 (5)	0.2917 (13)	0.0735 (11)	0.0236 (19)	0.500 (2)
H4AA	0.2198	0.2253	0.0426	0.028*	0.500 (2)
C5A	0.2073 (6)	0.3829 (2)	0.0270 (2)	0.0222 (8)	0.500 (2)
H5AA	0.2332	0.3813	−0.0381	0.027*	0.500 (2)
C6A	0.1858 (6)	0.4815 (2)	0.0724 (2)	0.0193 (8)	0.500 (2)
H6AA	0.1953	0.5475	0.0388	0.023*	0.500 (2)
C2B	−0.0552 (7)	0.4023 (2)	0.1721 (2)	0.0220 (8)	0.500 (2)
H2BA	−0.2160	0.4145	0.2028	0.026*	0.500 (2)
C3B	−0.0253 (8)	0.3024 (3)	0.1303 (3)	0.0276 (9)	0.500 (2)
H3BA	−0.1718	0.2470	0.1306	0.033*	0.500 (2)
C4B	0.203 (5)	0.2816 (13)	0.0897 (11)	0.023 (2)	0.500 (2)
H4BA	0.2230	0.2116	0.0642	0.027*	0.500 (2)
C5B	0.4184 (6)	0.3673 (2)	0.0852 (2)	0.0255 (9)	0.500 (2)
H5BA	0.5776	0.3553	0.0538	0.031*	0.500 (2)
C6B	0.3922 (6)	0.4675 (2)	0.1271 (2)	0.0214 (8)	0.500 (2)
H6BA	0.5358	0.5241	0.1274	0.026*	0.500 (2)
N1	0.2242 (2)	0.72689 (9)	0.45092 (9)	0.0187 (3)
C8	0.0377 (3)	0.81391 (12)	0.46689 (12)	0.0274 (4)
H8A	−0.1571	0.7832	0.4706	0.033*
H8B	0.0268	0.8651	0.4134	0.033*
C9	0.1576 (4)	0.87271 (13)	0.55883 (13)	0.0374 (5)
H9A	0.3480	0.9064	0.5530	0.045*
H9B	0.0319	0.9314	0.5703	0.045*
C10	0.3616 (4)	0.71670 (14)	0.62119 (12)	0.0330 (4)
H10A	0.3772	0.6673	0.6759	0.040*
H10B	0.5552	0.7478	0.6160	0.040*
C11	0.2460 (3)	0.65330 (12)	0.53168 (11)	0.0257 (4)
H11A	0.3746	0.5950	0.5217	0.031*
H11B	0.0557	0.6194	0.5373	0.031*
N4	0.5044 (3)	0.73922 (10)	0.26441 (10)	0.0217 (3)
N2	0.3561 (2)	0.82518 (9)	0.21815 (9)	0.0182 (3)
C13	0.3853 (3)	0.82364 (12)	0.11680 (11)	0.0219 (4)
H13A	0.2914	0.7562	0.0862	0.026*
H13B	0.5898	0.8251	0.1096	0.026*
C14	0.2503 (3)	0.92070 (12)	0.06897 (12)	0.0280 (4)
H14A	0.2714	0.9192	0.0007	0.034*
H14B	0.0440	0.9171	0.0737	0.034*
C15	0.3467 (4)	1.02243 (12)	0.20977 (13)	0.0334 (4)
H15A	0.1412	1.0206	0.2156	0.040*
H15B	0.4364	1.0911	0.2393	0.040*
C16	0.4816 (3)	0.92776 (12)	0.26208 (12)	0.0267 (4)
H16A	0.6896	0.9322	0.2603	0.032*
H16B	0.4514	0.9308	0.3295	0.032*
H3N	−0.035 (3)	0.6311 (12)	0.3652 (11)	0.024 (4)*
H4N	0.674 (4)	0.7378 (13)	0.2627 (12)	0.032 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01465 (19)	0.01504 (19)	0.0181 (3)	0.00138 (14)	−0.00015 (16)	0.00092 (16)
O1	0.0163 (5)	0.0179 (5)	0.0238 (7)	0.0023 (4)	−0.0004 (4)	0.0032 (5)
O2	0.0187 (5)	0.0187 (5)	0.0201 (7)	0.0048 (4)	−0.0027 (5)	−0.0049 (5)
O3	0.0424 (7)	0.0456 (7)	0.0272 (8)	−0.0048 (6)	0.0110 (6)	−0.0135 (6)
O4	0.0410 (7)	0.0185 (6)	0.0328 (8)	−0.0035 (5)	0.0047 (6)	0.0074 (5)
N3	0.0157 (6)	0.0174 (6)	0.0196 (8)	−0.0032 (5)	−0.0004 (6)	−0.0047 (6)
C1	0.0163 (7)	0.0169 (7)	0.0168 (9)	0.0032 (6)	−0.0004 (6)	−0.0007 (7)
C2A	0.0189 (16)	0.0240 (16)	0.0173 (19)	0.0026 (13)	0.0012 (15)	0.0018 (14)
C3A	0.0257 (18)	0.0142 (15)	0.026 (2)	−0.0001 (14)	−0.0026 (18)	0.0050 (15)
C4A	0.028 (3)	0.023 (4)	0.020 (4)	0.006 (3)	0.000 (4)	−0.005 (3)
C5A	0.0229 (17)	0.0264 (17)	0.0173 (19)	0.0017 (13)	0.0037 (15)	−0.0025 (14)
C6A	0.0189 (16)	0.0177 (14)	0.0203 (19)	−0.0018 (12)	0.0000 (15)	0.0051 (13)
C2B	0.0207 (17)	0.0256 (16)	0.020 (2)	0.0007 (13)	0.0047 (16)	0.0038 (14)
C3B	0.0274 (19)	0.0203 (16)	0.033 (2)	−0.0035 (15)	0.0000 (18)	0.0058 (16)
C4B	0.033 (3)	0.012 (2)	0.022 (5)	0.009 (2)	−0.003 (4)	0.005 (3)
C5B	0.0223 (16)	0.0326 (17)	0.022 (2)	0.0087 (13)	0.0020 (15)	−0.0064 (15)
C6B	0.0180 (16)	0.0232 (15)	0.022 (2)	0.0006 (12)	0.0003 (14)	0.0008 (14)
N1	0.0203 (6)	0.0183 (6)	0.0169 (8)	0.0005 (5)	0.0007 (6)	−0.0030 (6)
C8	0.0283 (8)	0.0213 (8)	0.0322 (11)	0.0036 (7)	0.0028 (8)	−0.0077 (7)
C9	0.0410 (10)	0.0298 (9)	0.0412 (13)	0.0025 (8)	0.0063 (9)	−0.0134 (9)
C10	0.0393 (10)	0.0366 (10)	0.0228 (11)	−0.0037 (8)	0.0059 (8)	−0.0001 (8)
C11	0.0318 (9)	0.0248 (8)	0.0207 (10)	−0.0010 (7)	0.0052 (8)	0.0026 (8)
N4	0.0140 (6)	0.0227 (7)	0.0279 (9)	0.0020 (5)	0.0007 (6)	0.0088 (6)
N2	0.0222 (6)	0.0142 (6)	0.0172 (8)	0.0013 (5)	−0.0011 (6)	0.0035 (6)
C13	0.0272 (8)	0.0201 (8)	0.0177 (10)	−0.0015 (6)	0.0022 (7)	−0.0006 (7)
C14	0.0341 (9)	0.0240 (8)	0.0241 (11)	−0.0027 (7)	−0.0006 (8)	0.0055 (7)
C15	0.0449 (10)	0.0179 (8)	0.0381 (12)	−0.0018 (7)	0.0097 (9)	−0.0020 (8)
C16	0.0345 (9)	0.0223 (8)	0.0224 (10)	−0.0063 (7)	0.0040 (8)	−0.0034 (7)

Geometric parameters (Å, º) top

P1—O1	1.4705 (10)	C5B—C6B	1.387 (4)
P1—O2	1.5975 (10)	C5B—H5BA	0.9500
P1—N4	1.6295 (13)	C6B—H6BA	0.9500
P1—N3	1.6331 (13)	N1—C8	1.4645 (17)
O2—C1	1.4068 (16)	N1—C11	1.4663 (19)
O3—C9	1.421 (2)	C8—C9	1.510 (2)
O3—C10	1.4286 (19)	C8—H8A	0.9900
O4—C15	1.4233 (19)	C8—H8B	0.9900
O4—C14	1.4249 (17)	C9—H9A	0.9900
N3—N1	1.4297 (17)	C9—H9B	0.9900
N3—H3N	0.823 (15)	C10—C11	1.505 (2)
C1—C2A	1.354 (3)	C10—H10A	0.9900
C1—C2B	1.358 (3)	C10—H10B	0.9900
C1—C6B	1.384 (3)	C11—H11A	0.9900
C1—C6A	1.399 (3)	C11—H11B	0.9900
C2A—C3A	1.382 (4)	N4—N2	1.4186 (16)
C2A—H2AA	0.9500	N4—H4N	0.811 (16)
C3A—C4A	1.421 (17)	N2—C16	1.4656 (18)
C3A—H3AA	0.9500	N2—C13	1.4674 (18)
C4A—C5A	1.316 (15)	C13—C14	1.510 (2)
C4A—H4AA	0.9500	C13—H13A	0.9900
C5A—C6A	1.389 (4)	C13—H13B	0.9900
C5A—H5AA	0.9500	C14—H14A	0.9900
C6A—H6AA	0.9500	C14—H14B	0.9900
C2B—C3B	1.388 (4)	C15—C16	1.512 (2)
C2B—H2BA	0.9500	C15—H15A	0.9900
C3B—C4B	1.33 (2)	C15—H15B	0.9900
C3B—H3BA	0.9500	C16—H16A	0.9900
C4B—C5B	1.44 (2)	C16—H16B	0.9900
C4B—H4BA	0.9500

O1—P1—O2	114.63 (5)	N1—C8—H8A	109.9
O1—P1—N4	108.95 (6)	C9—C8—H8A	109.9
O2—P1—N4	108.62 (6)	N1—C8—H8B	109.9
O1—P1—N3	119.86 (6)	C9—C8—H8B	109.9
O2—P1—N3	96.87 (6)	H8A—C8—H8B	108.3
N4—P1—N3	106.95 (7)	O3—C9—C8	112.07 (14)
C1—O2—P1	122.17 (8)	O3—C9—H9A	109.2
C9—O3—C10	109.51 (13)	C8—C9—H9A	109.2
C15—O4—C14	109.64 (12)	O3—C9—H9B	109.2
N1—N3—P1	115.73 (9)	C8—C9—H9B	109.2
N1—N3—H3N	116.7 (11)	H9A—C9—H9B	107.9
P1—N3—H3N	116.9 (11)	O3—C10—C11	111.43 (13)
C2A—C1—C6B	103.2 (2)	O3—C10—H10A	109.3
C2B—C1—C6B	122.9 (2)	C11—C10—H10A	109.3
C2A—C1—C6A	120.6 (2)	O3—C10—H10B	109.3
C2B—C1—C6A	103.1 (2)	C11—C10—H10B	109.3
C2A—C1—O2	120.66 (18)	H10A—C10—H10B	108.0
C2B—C1—O2	117.71 (18)	N1—C11—C10	109.01 (13)
C6B—C1—O2	119.37 (17)	N1—C11—H11A	109.9
C6A—C1—O2	118.26 (16)	C10—C11—H11A	109.9
C1—C2A—C3A	120.0 (3)	N1—C11—H11B	109.9
C1—C2A—H2AA	120.0	C10—C11—H11B	109.9
C3A—C2A—H2AA	120.0	H11A—C11—H11B	108.3
C2A—C3A—C4A	118.2 (7)	N2—N4—P1	122.73 (9)
C2A—C3A—H3AA	120.9	N2—N4—H4N	118.0 (12)
C4A—C3A—H3AA	120.9	P1—N4—H4N	117.8 (12)
C5A—C4A—C3A	121.4 (13)	N4—N2—C16	108.27 (11)
C5A—C4A—H4AA	119.3	N4—N2—C13	109.67 (11)
C3A—C4A—H4AA	119.3	C16—N2—C13	109.55 (11)
C4A—C5A—C6A	120.4 (8)	N2—C13—C14	109.89 (12)
C4A—C5A—H5AA	119.8	N2—C13—H13A	109.7
C6A—C5A—H5AA	119.8	C14—C13—H13A	109.7
C5A—C6A—C1	119.0 (3)	N2—C13—H13B	109.7
C5A—C6A—H6AA	120.5	C14—C13—H13B	109.7
C1—C6A—H6AA	120.5	H13A—C13—H13B	108.2
C1—C2B—C3B	118.6 (3)	O4—C14—C13	111.09 (12)
C1—C2B—H2BA	120.7	O4—C14—H14A	109.4
C3B—C2B—H2BA	120.7	C13—C14—H14A	109.4
C4B—C3B—C2B	122.1 (8)	O4—C14—H14B	109.4
C4B—C3B—H3BA	119.0	C13—C14—H14B	109.4
C2B—C3B—H3BA	119.0	H14A—C14—H14B	108.0
C3B—C4B—C5B	118.9 (13)	O4—C15—C16	111.29 (13)
C3B—C4B—H4BA	120.6	O4—C15—H15A	109.4
C5B—C4B—H4BA	120.6	C16—C15—H15A	109.4
C6B—C5B—C4B	119.7 (9)	O4—C15—H15B	109.4
C6B—C5B—H5BA	120.2	C16—C15—H15B	109.4
C4B—C5B—H5BA	120.2	H15A—C15—H15B	108.0
C1—C6B—C5B	117.8 (3)	N2—C16—C15	110.24 (13)
C1—C6B—H6BA	121.1	N2—C16—H16A	109.6
C5B—C6B—H6BA	121.1	C15—C16—H16A	109.6
N3—N1—C8	108.48 (11)	N2—C16—H16B	109.6
N3—N1—C11	111.34 (11)	C15—C16—H16B	109.6
C8—N1—C11	109.63 (13)	H16A—C16—H16B	108.1
N1—C8—C9	108.73 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.823 (15)	2.093 (16)	2.8951 (16)	164.9 (15)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₃N₄O₄P
M_r	342.33
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	4.7469 (2), 12.3528 (5), 14.2149 (5)
α, β, γ (°)	90.542 (3), 98.389 (4), 93.009 (4)
V (Å³)	823.35 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur S diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.877, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10043, 2888, 2272
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.070, 0.99
No. of reflections	2888
No. of parameters	262
No. of restraints	162
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.32

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1ⁱ	0.823 (15)	2.093 (16)	2.8951 (16)	164.9 (15)

Symmetry code: (i) x−1, y, z.

Acknowledgements

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

References

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