p-Tolyl bis­(cyclo­hexyl­amido)­phosphinate

Raissi Shabari, A.; Pourayoubi, M.; Taghizadeh, A.; Ghoreishi, F.; Vahdani, B.

doi:10.1107/S1600536811029722

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2167

doi:10.1107/S1600536811029722

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p-Tolyl bis(cyclohexylamido)phosphinate

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi,^b Afsaneh Taghizadeh,^a Farnaz Ghoreishi ^a and Banafsheh Vahdani ^a

^aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran
^*Correspondence e-mail: a.raissi_shabari@yahoo.com

(Received 13 July 2011; accepted 22 July 2011; online 30 July 2011)

The P atom in the title molecule, C₁₉H₃₁N₂O₂P, is in a distorted tetrahedral configuration with the bond angles in the range 101.48 (10)–118.58 (9)°. The N—H units have a syn orientation with respect to one another. In the crystal, molecules are connected via two different intermolecular N—H⋯O(P) hydrogen bonds into chains along the a axis in which the O atom of the P=O group acts as a double acceptor.

Related literature

For background to phosphoramidate compounds, see: Pourayoubi et al. (2011 ). For bond lengths in related structures, see: Sabbaghi et al. (2011 ); Rudd et al. (1996 ). For double hydrogen-bond acceptors, see: Steiner (2002 ).

Experimental

Crystal data

C₁₉H₃₁N₂O₂P
M_r = 350.43
Monoclinic, P 2₁ /a
a = 9.131 (5) Å
b = 19.333 (5) Å
c = 11.291 (5) Å
β = 99.247 (5)°
V = 1967.3 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 291 K
0.38 × 0.12 × 0.08 mm

Data collection

Stoe IPDS II image plate diffractometer
Absorption correction: multi-scan [MULABS (Blessing, 1995 ) in PLATON (Spek, 2009 )] T_min = 0.992, T_max = 1.000
14835 measured reflections
5296 independent reflections
1925 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.090
S = 0.76
5296 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.76	2.23	2.969 (3)	163
N2—H2⋯O1ⁱ	0.75	2.25	2.975 (3)	162
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z]$ .

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009) and enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029722/lh5287sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029722/lh5287Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029722/lh5287Isup3.cml

checkCIF report

Comment top

The structure determination of title compound was performed as a part of a project in our laboratory on the synthesis of new phosphoramidate compounds (Pourayoubi et al., 2011).

The P═O (1.4670 (17) Å), P—O (1.6105 (17) Å) and P—N (1.6131 (19) Å and 1.6152 (18) Å) bond lengths and the C—O—P (123.52 (15)°) and C—N—P (125.28 (16)° and 123.76 (16)°) angles match those found for other compounds with the [(N)(N)P(O)(O)] skeleton (Sabbaghi et al., 2011).

The tetrahedral configuration of phosphorus atom is significantly distorted (Fig. 1) as it has been noted for other phosphoramides and their chalco-derivatives (Rudd et al., 1996); the bond angles at the P atom vary in the range from 101.48 (10)° [for O2—P1—N2 angle] to 118.58 (9)° [for O1—P1—N2 angle]. Cyclohexyl groups are in a chair conformation with the adjacent NH groups oriented equatorially.

The O atom of the P═O group acts as a double hydrogen-bond acceptor (Steiner, 2002). In the crystal structure, each molecule is hydrogen-bonded to two adjacent molecules through [N—H]₂···O(P) hydrogen bonds forming linear chains parallel to [100] (Fig. 2, Table 1).

Related literature top

For background to phosphoramidate compounds, see: Pourayoubi et al. (2011). For bond lengths in related structures, see: Sabbaghi et al. (2011); Rudd et al. (1996). For double hydrogen-bond acceptors, see: Steiner (2002).

Experimental top

Synthesis of 4-CH₃–C₆H₄–O–P(O)Cl₂ 4-CH₃–C₆H₄–O–H (0.18 mol) and P(O)Cl₃ (0.54 mol) were refluxed for 8 h and afterwards the excess of P(O)Cl₃ was removed in vacuum.

Synthesis of title compound To a solution of 4-CH₃–C₆H₄–O–P(O)Cl₂ (2 mmol) in chloroform (20 ml), a solution of cyclohexylamine (8 mmol) in chloroform (15 ml) was added at 273 K. After 4 h of stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water, and then re-crystallized from a mixture of CHCl₃/n-C₇H₁₆. Single crystals, suitable for crystallography, were obtained from a solution of the title compound in acetonitrile after slow evaporation at room temperature.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level.
	Fig. 2. A view of the crystal packing showing the formation of chains through N—H···O hydrogen bonds (shown as dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

1-{[bis(phenylamino)phosphoryl]oxy}-4-methylbenzene top

Crystal data top

C₁₉H₃₁N₂O₂P	F(000) = 760
M_r = 350.43	D_x = 1.183 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2yab	Cell parameters from 3912 reflections
a = 9.131 (5) Å	θ = 1.8–29.5°
b = 19.333 (5) Å	µ = 0.15 mm⁻¹
c = 11.291 (5) Å	T = 291 K
β = 99.247 (5)°	Block, colourless
V = 1967.3 (15) Å³	0.38 × 0.12 × 0.08 mm
Z = 4

Data collection top

Stoe IPDS II image plate diffractometer	5296 independent reflections
Radiation source: fine-focus sealed tube	1925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 1.8°
ω scans	h = −12→9
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]	k = −22→26
T_min = 0.992, T_max = 1.000	l = −15→15
14835 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 0.76	w = 1/[σ²(F_o²) + (0.0255P)²] where P = (F_o² + 2F_c²)/3
5296 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₃₁N₂O₂P	V = 1967.3 (15) Å³
M_r = 350.43	Z = 4
Monoclinic, P2₁/a	Mo Kα radiation
a = 9.131 (5) Å	µ = 0.15 mm⁻¹
b = 19.333 (5) Å	T = 291 K
c = 11.291 (5) Å	0.38 × 0.12 × 0.08 mm
β = 99.247 (5)°

Data collection top

Stoe IPDS II image plate diffractometer	5296 independent reflections
Absorption correction: multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]	1925 reflections with I > 2σ(I)
T_min = 0.992, T_max = 1.000	R_int = 0.091
14835 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 0.76	Δρ_max = 0.21 e Å⁻³
5296 reflections	Δρ_min = −0.26 e Å⁻³
218 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	0.71746 (8)	0.80003 (4)	0.50141 (5)	0.03970 (16)
O1	0.87988 (16)	0.79943 (9)	0.51391 (11)	0.0481 (4)
O2	0.66002 (18)	0.87739 (8)	0.46763 (13)	0.0530 (5)
N1	0.6357 (2)	0.74705 (11)	0.40180 (15)	0.0540 (6)
H1	0.5695	0.7286	0.4204	0.065*
N2	0.6418 (2)	0.78465 (10)	0.61857 (13)	0.0488 (6)
H2	0.5753	0.7613	0.6076	0.059*
C1	0.7075 (3)	0.71015 (13)	0.31259 (16)	0.0433 (6)
H1A	0.7944	0.7370	0.2994	0.052*
C2	0.7592 (3)	0.63929 (14)	0.3529 (2)	0.0637 (8)
H2A	0.6753	0.6125	0.3700	0.076*
H2B	0.8301	0.6429	0.4264	0.076*
C3	0.8310 (4)	0.60189 (16)	0.2589 (2)	0.0779 (9)
H3A	0.8596	0.5557	0.2870	0.093*
H3B	0.9199	0.6264	0.2465	0.093*
C4	0.7244 (3)	0.59729 (16)	0.1408 (2)	0.0749 (9)
H4A	0.7738	0.5756	0.0806	0.090*
H4B	0.6397	0.5690	0.1513	0.090*
C5	0.6727 (4)	0.66822 (17)	0.0996 (2)	0.0755 (9)
H5A	0.6010	0.6644	0.0266	0.091*
H5B	0.7565	0.6947	0.0813	0.091*
C6	0.6017 (3)	0.70671 (14)	0.19495 (17)	0.0579 (7)
H6A	0.5753	0.7532	0.1672	0.070*
H6B	0.5116	0.6831	0.2070	0.070*
C7	0.6472 (3)	0.83281 (12)	0.71992 (17)	0.0434 (6)
H7A	0.7147	0.8706	0.7074	0.052*
C8	0.7099 (3)	0.79764 (16)	0.83611 (18)	0.0739 (9)
H8A	0.8094	0.7815	0.8318	0.089*
H8B	0.6494	0.7577	0.8473	0.089*
C9	0.7148 (4)	0.84609 (17)	0.94366 (19)	0.0768 (10)
H9A	0.7512	0.8210	1.0168	0.092*
H9B	0.7830	0.8838	0.9366	0.092*
C10	0.5655 (4)	0.87468 (17)	0.9507 (2)	0.0772 (10)
H10A	0.5721	0.9065	1.0178	0.093*
H10B	0.4990	0.8374	0.9642	0.093*
C11	0.5044 (4)	0.91182 (17)	0.8365 (2)	0.0913 (11)
H11A	0.5660	0.9517	0.8271	0.110*
H11B	0.4051	0.9282	0.8410	0.110*
C12	0.4996 (3)	0.86385 (16)	0.7272 (2)	0.0715 (9)
H12A	0.4285	0.8271	0.7321	0.086*
H12B	0.4662	0.8900	0.6545	0.086*
C13	0.7349 (3)	0.92389 (13)	0.40431 (19)	0.0448 (6)
C14	0.7785 (4)	0.98514 (16)	0.4565 (2)	0.0709 (9)
H14A	0.7614	0.9946	0.5338	0.085*
C15	0.8477 (4)	1.03306 (16)	0.3956 (2)	0.0788 (10)
H15A	0.8768	1.0749	0.4327	0.095*
C16	0.8753 (3)	1.02153 (15)	0.2822 (2)	0.0572 (7)
C17	0.8292 (3)	0.95964 (15)	0.2303 (2)	0.0596 (8)
H17A	0.8452	0.9504	0.1526	0.072*
C18	0.7597 (3)	0.91060 (14)	0.2906 (2)	0.0566 (7)
H18A	0.7298	0.8687	0.2538	0.068*
C19	0.9524 (4)	1.07473 (16)	0.2168 (3)	0.0979 (12)
H19A	1.0489	1.0841	0.2614	0.147*
H19B	0.8950	1.1166	0.2084	0.147*
H19C	0.9623	1.0575	0.1388	0.147*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0361 (3)	0.0466 (4)	0.0374 (3)	0.0011 (4)	0.0089 (2)	−0.0014 (3)
O1	0.0345 (10)	0.0549 (12)	0.0549 (9)	−0.0006 (10)	0.0065 (7)	0.0005 (8)
O2	0.0502 (12)	0.0530 (12)	0.0600 (10)	0.0080 (10)	0.0210 (8)	0.0112 (8)
N1	0.0438 (13)	0.0734 (16)	0.0488 (10)	−0.0117 (12)	0.0196 (9)	−0.0200 (10)
N2	0.0561 (13)	0.0520 (15)	0.0416 (9)	−0.0139 (12)	0.0182 (9)	−0.0067 (9)
C1	0.0433 (14)	0.0487 (18)	0.0403 (11)	−0.0051 (14)	0.0141 (10)	−0.0057 (11)
C2	0.073 (2)	0.066 (2)	0.0506 (14)	0.0140 (18)	0.0063 (13)	0.0064 (14)
C3	0.083 (3)	0.067 (2)	0.084 (2)	0.029 (2)	0.0128 (17)	−0.0021 (16)
C4	0.081 (2)	0.071 (2)	0.0782 (19)	−0.003 (2)	0.0282 (17)	−0.0296 (17)
C5	0.092 (2)	0.088 (3)	0.0452 (14)	0.011 (2)	0.0089 (14)	−0.0147 (15)
C6	0.0702 (18)	0.0572 (18)	0.0452 (12)	0.0103 (17)	0.0056 (12)	−0.0002 (13)
C7	0.0493 (17)	0.0437 (16)	0.0391 (12)	−0.0108 (13)	0.0127 (11)	−0.0037 (11)
C8	0.084 (2)	0.088 (2)	0.0474 (14)	0.028 (2)	0.0033 (13)	−0.0066 (15)
C9	0.085 (2)	0.101 (3)	0.0421 (14)	0.013 (2)	0.0043 (14)	−0.0095 (14)
C10	0.083 (2)	0.100 (3)	0.0533 (16)	−0.006 (2)	0.0253 (15)	−0.0225 (15)
C11	0.092 (3)	0.107 (3)	0.0727 (19)	0.041 (2)	0.0048 (17)	−0.0266 (18)
C12	0.065 (2)	0.094 (2)	0.0522 (15)	0.0257 (19)	−0.0001 (13)	−0.0125 (15)
C13	0.0411 (16)	0.0481 (18)	0.0457 (13)	0.0065 (14)	0.0084 (11)	0.0076 (12)
C14	0.110 (3)	0.058 (2)	0.0485 (15)	−0.009 (2)	0.0244 (16)	−0.0067 (14)
C15	0.109 (3)	0.058 (2)	0.0689 (18)	−0.021 (2)	0.0120 (18)	−0.0091 (15)
C16	0.0531 (19)	0.057 (2)	0.0602 (16)	−0.0057 (17)	0.0047 (13)	0.0123 (15)
C17	0.067 (2)	0.068 (2)	0.0466 (14)	−0.0009 (17)	0.0162 (13)	0.0010 (14)
C18	0.0625 (19)	0.0537 (19)	0.0560 (15)	−0.0107 (16)	0.0168 (13)	−0.0086 (13)
C19	0.102 (3)	0.089 (3)	0.103 (2)	−0.028 (2)	0.018 (2)	0.0294 (19)

Geometric parameters (Å, º) top

P1—O1	1.4670 (17)	C8—C9	1.528 (3)
P1—O2	1.6105 (17)	C8—H8A	0.9700
P1—N1	1.6131 (19)	C8—H8B	0.9700
P1—N2	1.6152 (18)	C9—C10	1.486 (4)
O2—C13	1.394 (3)	C9—H9A	0.9700
N1—C1	1.472 (3)	C9—H9B	0.9700
N1—H1	0.7593	C10—C11	1.503 (4)
N2—C7	1.470 (3)	C10—H10A	0.9700
N2—H2	0.7510	C10—H10B	0.9700
C1—C2	1.496 (3)	C11—C12	1.539 (3)
C1—C6	1.513 (3)	C11—H11A	0.9700
C1—H1A	0.9800	C11—H11B	0.9700
C2—C3	1.517 (3)	C12—H12A	0.9700
C2—H2A	0.9700	C12—H12B	0.9700
C2—H2B	0.9700	C13—C14	1.354 (3)
C3—C4	1.522 (3)	C13—C18	1.364 (3)
C3—H3A	0.9700	C14—C15	1.367 (4)
C3—H3B	0.9700	C14—H14A	0.9300
C4—C5	1.500 (4)	C15—C16	1.362 (3)
C4—H4A	0.9700	C15—H15A	0.9300
C4—H4B	0.9700	C16—C17	1.369 (3)
C5—C6	1.536 (3)	C16—C19	1.505 (4)
C5—H5A	0.9700	C17—C18	1.380 (3)
C5—H5B	0.9700	C17—H17A	0.9300
C6—H6A	0.9700	C18—H18A	0.9300
C6—H6B	0.9700	C19—H19A	0.9600
C7—C12	1.490 (3)	C19—H19B	0.9600
C7—C8	1.506 (3)	C19—H19C	0.9600
C7—H7A	0.9800

O1—P1—O2	108.41 (10)	C7—C8—C9	112.0 (2)
O1—P1—N1	114.19 (10)	C7—C8—H8A	109.2
O2—P1—N1	109.13 (10)	C9—C8—H8A	109.2
O1—P1—N2	118.58 (9)	C7—C8—H8B	109.2
O2—P1—N2	101.48 (10)	C9—C8—H8B	109.2
N1—P1—N2	104.07 (11)	H8A—C8—H8B	107.9
C13—O2—P1	123.52 (15)	C10—C9—C8	111.1 (2)
C1—N1—P1	125.28 (16)	C10—C9—H9A	109.4
C1—N1—H1	115.1	C8—C9—H9A	109.4
P1—N1—H1	113.9	C10—C9—H9B	109.4
C7—N2—P1	123.76 (16)	C8—C9—H9B	109.4
C7—N2—H2	115.8	H9A—C9—H9B	108.0
P1—N2—H2	114.6	C9—C10—C11	110.4 (2)
N1—C1—C2	112.93 (18)	C9—C10—H10A	109.6
N1—C1—C6	109.3 (2)	C11—C10—H10A	109.6
C2—C1—C6	110.6 (2)	C9—C10—H10B	109.6
N1—C1—H1A	107.9	C11—C10—H10B	109.6
C2—C1—H1A	107.9	H10A—C10—H10B	108.1
C6—C1—H1A	107.9	C10—C11—C12	111.1 (3)
C1—C2—C3	112.0 (2)	C10—C11—H11A	109.4
C1—C2—H2A	109.2	C12—C11—H11A	109.4
C3—C2—H2A	109.2	C10—C11—H11B	109.4
C1—C2—H2B	109.2	C12—C11—H11B	109.4
C3—C2—H2B	109.2	H11A—C11—H11B	108.0
H2A—C2—H2B	107.9	C7—C12—C11	112.2 (2)
C2—C3—C4	110.7 (2)	C7—C12—H12A	109.2
C2—C3—H3A	109.5	C11—C12—H12A	109.2
C4—C3—H3A	109.5	C7—C12—H12B	109.2
C2—C3—H3B	109.5	C11—C12—H12B	109.2
C4—C3—H3B	109.5	H12A—C12—H12B	107.9
H3A—C3—H3B	108.1	C14—C13—C18	119.5 (2)
C5—C4—C3	110.1 (2)	C14—C13—O2	118.4 (2)
C5—C4—H4A	109.6	C18—C13—O2	122.0 (2)
C3—C4—H4A	109.6	C13—C14—C15	120.1 (2)
C5—C4—H4B	109.6	C13—C14—H14A	120.0
C3—C4—H4B	109.6	C15—C14—H14A	120.0
H4A—C4—H4B	108.2	C16—C15—C14	122.1 (3)
C4—C5—C6	111.9 (2)	C16—C15—H15A	118.9
C4—C5—H5A	109.2	C14—C15—H15A	118.9
C6—C5—H5A	109.2	C15—C16—C17	117.1 (3)
C4—C5—H5B	109.2	C15—C16—C19	121.4 (3)
C6—C5—H5B	109.2	C17—C16—C19	121.5 (3)
H5A—C5—H5B	107.9	C16—C17—C18	121.6 (2)
C1—C6—C5	110.8 (2)	C16—C17—H17A	119.2
C1—C6—H6A	109.5	C18—C17—H17A	119.2
C5—C6—H6A	109.5	C13—C18—C17	119.6 (2)
C1—C6—H6B	109.5	C13—C18—H18A	120.2
C5—C6—H6B	109.5	C17—C18—H18A	120.2
H6A—C6—H6B	108.1	C16—C19—H19A	109.5
N2—C7—C12	112.36 (19)	C16—C19—H19B	109.5
N2—C7—C8	110.7 (2)	H19A—C19—H19B	109.5
C12—C7—C8	110.73 (19)	C16—C19—H19C	109.5
N2—C7—H7A	107.6	H19A—C19—H19C	109.5
C12—C7—H7A	107.6	H19B—C19—H19C	109.5
C8—C7—H7A	107.6

O1—P1—O2—C13	29.02 (19)	N2—C7—C8—C9	−179.1 (2)
N1—P1—O2—C13	−95.91 (19)	C12—C7—C8—C9	−53.9 (3)
N2—P1—O2—C13	154.63 (17)	C7—C8—C9—C10	56.4 (3)
O1—P1—N1—C1	−11.6 (2)	C8—C9—C10—C11	−57.2 (3)
O2—P1—N1—C1	109.9 (2)	C9—C10—C11—C12	56.4 (3)
N2—P1—N1—C1	−142.37 (19)	N2—C7—C12—C11	177.5 (2)
O1—P1—N2—C7	70.6 (2)	C8—C7—C12—C11	53.2 (3)
O2—P1—N2—C7	−48.0 (2)	C10—C11—C12—C7	−55.1 (4)
N1—P1—N2—C7	−161.28 (18)	P1—O2—C13—C14	−121.7 (2)
P1—N1—C1—C2	94.3 (2)	P1—O2—C13—C18	61.1 (3)
P1—N1—C1—C6	−142.1 (2)	C18—C13—C14—C15	−0.4 (4)
N1—C1—C2—C3	179.3 (2)	O2—C13—C14—C15	−177.7 (3)
C6—C1—C2—C3	56.4 (3)	C13—C14—C15—C16	−0.1 (5)
C1—C2—C3—C4	−57.1 (3)	C14—C15—C16—C17	0.7 (5)
C2—C3—C4—C5	56.1 (3)	C14—C15—C16—C19	−179.6 (3)
C3—C4—C5—C6	−55.9 (3)	C15—C16—C17—C18	−0.9 (4)
N1—C1—C6—C5	−179.8 (2)	C19—C16—C17—C18	179.5 (3)
C2—C1—C6—C5	−54.8 (3)	C14—C13—C18—C17	0.2 (4)
C4—C5—C6—C1	55.7 (3)	O2—C13—C18—C17	177.4 (2)
P1—N2—C7—C12	110.5 (2)	C16—C17—C18—C13	0.4 (4)
P1—N2—C7—C8	−125.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.76	2.23	2.969 (3)	163
N2—H2···O1ⁱ	0.75	2.25	2.975 (3)	162

Symmetry code: (i) x−1/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₃₁N₂O₂P
M_r	350.43
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	291
a, b, c (Å)	9.131 (5), 19.333 (5), 11.291 (5)
β (°)	99.247 (5)
V (Å³)	1967.3 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.38 × 0.12 × 0.08

Data collection
Diffractometer	Stoe IPDS II image plate diffractometer
Absorption correction	Multi-scan [MULABS (Blessing, 1995) in PLATON (Spek, 2009)]
T_min, T_max	0.992, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	14835, 5296, 1925
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.090, 0.76
No. of reflections	5296
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.26

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.76	2.23	2.969 (3)	162.8
N2—H2···O1ⁱ	0.75	2.25	2.975 (3)	161.7

Symmetry code: (i) x−1/2, −y+3/2, z.

Acknowledgements

Support of this investigation by North Tehran Branch, Islamic Azad University, is gratefully acknowledged.

References

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