p-Tolyl bis­(p-tolyl­amido)phosphate

Pourayoubi, M.; Ghadimi, S.; Ebrahimi Valmoozi, A.A.; Banan, A.R.

doi:10.1107/S1600536809028281

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1973

doi:10.1107/S1600536809028281

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p-Tolyl bis(p-tolylamido)phosphate

Mehrdad Pourayoubi,^a Saied Ghadimi,^b ^* Ali Asghar Ebrahimi Valmoozi ^b and Ali Reza Banan ^b

^aDepartment of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Chemistry, Imam Hossein University, PO Box 16575-347, Tehran, Iran
^*Correspondence e-mail: ghadimi_saied@yahoo.com

(Received 25 June 2009; accepted 17 July 2009; online 25 July 2009)

In the title compound, C₂₁H₂₃N₂O₂P, the P atom exhibits tetrahedral coordination; the P—N bond lengths are relatively short [1.6297 (13) and 1.6424 (13) Å]. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into a zigzag chain running along the c axis.

Related literature

For related compounds, see: Pourayoubi & Sabbaghi (2007 ); Ghadimi et al. (2007 ); Gholivand et al. (2001 ). For bond-length data, see: Corbridge (1995 ).

Experimental

Crystal data

C₂₁H₂₃N₂O₂P
M_r = 366.38
Monoclinic, P 2₁ /c
a = 14.0977 (6) Å
b = 14.7657 (6) Å
c = 9.5155 (4) Å
β = 104.676 (1)°
V = 1916.14 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 100 K
0.40 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.939, T_max = 0.969
18737 measured reflections
5555 independent reflections
4484 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.107
S = 1.02
5555 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.878 (9)	1.928 (7)	2.805 (2)	176 (2)
N2—H2N⋯O2ⁱⁱ	0.881 (9)	2.209 (7)	3.068 (2)	165 (2)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028281/ng2606sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028281/ng2606Isup2.hkl

checkCIF report

Comment top

In the previous works about phosphoramidates and phosphoric acid esters, some derivatives have been structurally discussed such as [(CH₃)₂N][4-H₃C—C₆H₄—O]P(O)CN (Ghadimi et al., 2007), [(CH₃)₂N]P(O)[O—C₆H₄-(4-NO₂)]₂ (Gholivand et al., 2001) and [(C₆H₅CH₂)(CH(CH₃)₂)NH₂][CCl₃C(O)NHP(O)(O)(OCH₃)] (Pourayoubi & Sabbaghi, 2007). Here, synthesis and crystal structure of a new phosphoramido acid ester, [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-4-CH₃]₂, are reported. The title compound was synthesized from the reaction of (4-tolyl)-dichlorophosphate with an excess amount of para-toluidine (1:4 mole ratios). Single crystals were obtained from CHCl₃/CH₃CN at room temperature. Molecular structure of [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-4-CH₃]₂ is shown in Fig. 1. The phosphorus atom has distorted tetrahedral configuration. The bond angles around P atom are in the range of 96.93 (6)° [for the O(2)—P(1)—N(1) angle] to 119.08 (7)° [for the O(1)—P(1)—N(1) angle]. The oxygen atom of OC₆H₄-4-CH₃ moiety has sp² character (the C(15)—O(2)—P(1) angle is 119.58 (9)°, also the P(1)—O(2) bond length of 1.6072 (11) Å is smaller than the P—O single bond length. The P(1)—O(1) bond length (1.4765 (11) Å) is longer than the normal P===O bond length [1.45 Å for P(O)Cl₃, (Corbridge, 1995)]. The P—N bond lengths in title compound are shorter than the P—N single bond length [1.77 Å for NaHPO₃NH₂, (Corbridge, 1995)]. Moreover, the nitrogen atoms have sp² hybridization. Sum of the surrounding angles around N(1) and N(2) atoms are 359.7° & 360.0°, respectively. H-bonded chain of title compound is formed via two different types of N—H···O===P hydrogen bond. A view of unit cell packing showing the N—H···O===P hydrogen bond is given in Fig. 2.

Related literature top

For related compounds, see: Pourayoubi & Sabbaghi (2007); Ghadimi et al. (2007); Gholivand et al. (2001). For bond-length data, see: Corbridge (1995).

Experimental top

To a solution of (4-tolyl)-dichlorophosphate (2.250 g, 10 mmol) in 15 ml dry acetonitrile, a solution of para-toluidine (4.286 g, 40 mmol) in 30 ml acetonitrile was added at 0°C. After 4 h stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals of the product were obtained from a solution of chloroform-acetonitrile (4:1) after a slow evaporation at room temperature. ¹H NMR (250.13 MHz, CDCl₃, 25°C, TMS), δ (p.p.m.): 2.17 (s, 6H, p-CH₃), 2.25 (s, 3H, p-CH₃), 6.95–7.00 (m, 8H, Ar—H), 7.03–7.15 (m, 4H, Ar—H), 8.15 (d, ²J(PNH) = 9.8 Hz, 2H, NH); ¹³C NMR (62.90 MHz, CDCl₃, 25°C, TMS), δ (p.p.m.): 20.69 (s, 2 C, p-CH₃), 2.77 (s, 1 C, p-CH₃), 117.98 (d, ³J(P,C) = 7.6 Hz, C_ortho), 120.77 (d, ³J(P,C) = 4.6 Hz, C_ortho), 129.81 (s), 129.96 (s), 130.47 (s), 134.24 (s), 138.70 (d, ²J(P,C) = 1.8 Hz, 2 C, C_ipso), 148.59 (d, ²J(P,C) = 6.5 Hz, 1 C, C_ipso); ³¹P{¹H} NMR (101.25 MHz, CDCl₃, 25°C, H₃PO₄ external), δ (p.p.m.): 1.23 (s); ³¹P NMR, δ (p.p.m.): 1.23 (t, ²J(HNP) = 9.8 Hz). IR (KBr, cm^-1): 3220 (NH), 2950, 2935, 1610, 1515, 1430, 1320, 1240 (P===O), 1190, 1150, 1125, 975, 915, 725.

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); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure and atom-labeling scheme for [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-4-CH₃]₂ (50% probability ellipsoids).
	Fig. 2. A view of unit cell packing of title compound.

p-Tolyl bis(p-tolylamido)phosphate top

Crystal data top

C₂₁H₂₃N₂O₂P	F(000) = 776
M_r = 366.38	D_x = 1.270 Mg m⁻³ D_m = 0 Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 552 reflections
a = 14.0977 (6) Å	θ = 3–30°
b = 14.7657 (6) Å	µ = 0.16 mm⁻¹
c = 9.5155 (4) Å	T = 100 K
β = 104.676 (1)°	Needle, colorless
V = 1916.14 (14) Å³	0.40 × 0.26 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	5555 independent reflections
Radiation source: fine-focus sealed tube	4484 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 30.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→19
T_min = 0.939, T_max = 0.969	k = −20→16
18737 measured reflections	l = −13→13

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) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0306P)² + 1.982P] where P = (F_o² + 2F_c²)/3
5555 reflections	(Δ/σ)_max < 0.001
243 parameters	Δρ_max = 0.62 e Å⁻³
2 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₂₁H₂₃N₂O₂P	V = 1916.14 (14) Å³
M_r = 366.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.0977 (6) Å	µ = 0.16 mm⁻¹
b = 14.7657 (6) Å	T = 100 K
c = 9.5155 (4) Å	0.40 × 0.26 × 0.20 mm
β = 104.676 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5555 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4484 reflections with I > 2σ(I)
T_min = 0.939, T_max = 0.969	R_int = 0.033
18737 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	2 restraints
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.62 e Å⁻³
5555 reflections	Δρ_min = −0.50 e Å⁻³
243 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	0.30676 (3)	0.73955 (3)	0.60541 (4)	0.01332 (9)
O1	0.37549 (8)	0.77353 (7)	0.52354 (11)	0.0174 (2)
O2	0.27068 (8)	0.81531 (7)	0.70157 (11)	0.0165 (2)
N1	0.34582 (9)	0.66666 (8)	0.73586 (13)	0.0154 (2)
H1N	0.3574 (14)	0.6865 (13)	0.8256 (12)	0.020 (5)*
N2	0.20970 (9)	0.69923 (9)	0.48821 (13)	0.0164 (2)
H2N	0.2157 (13)	0.6978 (12)	0.3983 (11)	0.014 (4)*
C1	0.37149 (10)	0.57578 (10)	0.71581 (15)	0.0153 (3)
C2	0.38112 (14)	0.51526 (11)	0.83062 (17)	0.0249 (3)
H2A	0.3725	0.5353	0.9192	0.030*
C3	0.40352 (14)	0.42486 (12)	0.81343 (19)	0.0269 (4)
H3A	0.4104	0.3853	0.8914	0.032*
C4	0.41580 (11)	0.39238 (11)	0.68168 (18)	0.0198 (3)
C5	0.40809 (11)	0.45397 (11)	0.56929 (17)	0.0189 (3)
H5A	0.4170	0.4339	0.4809	0.023*
C6	0.38729 (11)	0.54520 (10)	0.58541 (16)	0.0173 (3)
H6A	0.3840	0.5854	0.5091	0.021*
C7	0.43533 (13)	0.29353 (12)	0.6595 (2)	0.0277 (4)
H7A	0.4415	0.2845	0.5623	0.042*
H7B	0.3819	0.2578	0.6745	0.042*
H7C	0.4950	0.2755	0.7276	0.042*
C8	0.11965 (11)	0.66800 (10)	0.51075 (16)	0.0163 (3)
C9	0.04290 (12)	0.64951 (11)	0.38934 (16)	0.0209 (3)
H9A	0.0517	0.6582	0.2967	0.025*
C10	−0.04647 (12)	0.61819 (12)	0.40582 (18)	0.0227 (3)
H10A	−0.0964	0.6052	0.3237	0.027*
C11	−0.06289 (11)	0.60580 (11)	0.54274 (18)	0.0201 (3)
C12	0.01388 (12)	0.62506 (12)	0.66285 (17)	0.0222 (3)
H12A	0.0044	0.6177	0.7554	0.027*
C13	0.10467 (12)	0.65499 (11)	0.64861 (16)	0.0206 (3)
H13A	0.1552	0.6663	0.7309	0.025*
C14	−0.16075 (12)	0.57270 (13)	0.5597 (2)	0.0273 (4)
H14A	−0.1587	0.5683	0.6610	0.041*
H14B	−0.1746	0.5142	0.5151	0.041*
H14C	−0.2112	0.6146	0.5136	0.041*
C15	0.24805 (11)	0.90316 (10)	0.64444 (15)	0.0160 (3)
C16	0.31733 (11)	0.97067 (10)	0.68618 (16)	0.0173 (3)
H16A	0.3793	0.9576	0.7450	0.021*
C17	0.29238 (12)	1.05864 (11)	0.63823 (17)	0.0206 (3)
H17A	0.3381	1.1048	0.6667	0.025*
C18	0.20005 (12)	1.07898 (11)	0.54811 (17)	0.0227 (3)
C19	0.13342 (12)	1.00877 (12)	0.50624 (18)	0.0249 (3)
H19A	0.0722	1.0210	0.4446	0.030*
C20	0.15618 (12)	0.92020 (11)	0.55447 (17)	0.0215 (3)
H20A	0.1107	0.8738	0.5268	0.026*
C21	0.17365 (16)	1.17477 (13)	0.4986 (2)	0.0355 (4)
H21A	0.1079	1.1762	0.4380	0.053*
H21B	0.2182	1.1962	0.4446	0.053*
H21C	0.1781	1.2129	0.5818	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.01640 (17)	0.01403 (17)	0.00997 (15)	−0.00111 (13)	0.00415 (12)	0.00019 (13)
O1	0.0192 (5)	0.0202 (5)	0.0135 (5)	−0.0029 (4)	0.0054 (4)	0.0016 (4)
O2	0.0236 (5)	0.0143 (5)	0.0129 (4)	0.0008 (4)	0.0068 (4)	0.0008 (4)
N1	0.0225 (6)	0.0140 (6)	0.0100 (5)	−0.0003 (5)	0.0046 (4)	−0.0003 (4)
N2	0.0165 (6)	0.0222 (6)	0.0108 (5)	−0.0028 (5)	0.0041 (4)	−0.0006 (5)
C1	0.0152 (6)	0.0152 (7)	0.0154 (6)	−0.0011 (5)	0.0034 (5)	−0.0001 (5)
C2	0.0386 (9)	0.0204 (8)	0.0178 (7)	0.0034 (7)	0.0111 (6)	0.0029 (6)
C3	0.0383 (9)	0.0196 (8)	0.0239 (8)	0.0049 (7)	0.0102 (7)	0.0074 (6)
C4	0.0139 (6)	0.0170 (7)	0.0272 (8)	0.0010 (5)	0.0026 (6)	−0.0011 (6)
C5	0.0166 (7)	0.0203 (7)	0.0203 (7)	−0.0004 (6)	0.0054 (5)	−0.0043 (6)
C6	0.0196 (7)	0.0174 (7)	0.0157 (6)	−0.0011 (6)	0.0061 (5)	0.0005 (5)
C7	0.0245 (8)	0.0183 (8)	0.0375 (9)	0.0046 (6)	0.0025 (7)	−0.0010 (7)
C8	0.0170 (7)	0.0156 (7)	0.0166 (6)	−0.0004 (5)	0.0049 (5)	−0.0004 (5)
C9	0.0220 (7)	0.0248 (8)	0.0152 (6)	−0.0006 (6)	0.0033 (6)	0.0003 (6)
C10	0.0181 (7)	0.0253 (8)	0.0224 (7)	−0.0016 (6)	0.0010 (6)	−0.0010 (6)
C11	0.0178 (7)	0.0162 (7)	0.0269 (8)	0.0005 (6)	0.0068 (6)	0.0012 (6)
C12	0.0234 (7)	0.0255 (8)	0.0202 (7)	−0.0026 (6)	0.0100 (6)	0.0015 (6)
C13	0.0201 (7)	0.0259 (8)	0.0158 (6)	−0.0056 (6)	0.0044 (5)	−0.0013 (6)
C14	0.0192 (7)	0.0265 (9)	0.0369 (9)	−0.0019 (6)	0.0084 (7)	0.0020 (7)
C15	0.0213 (7)	0.0145 (7)	0.0131 (6)	0.0012 (5)	0.0063 (5)	0.0005 (5)
C16	0.0187 (7)	0.0181 (7)	0.0151 (6)	0.0017 (6)	0.0039 (5)	0.0000 (5)
C17	0.0248 (8)	0.0163 (7)	0.0200 (7)	−0.0015 (6)	0.0045 (6)	−0.0008 (6)
C18	0.0270 (8)	0.0186 (7)	0.0212 (7)	0.0046 (6)	0.0035 (6)	0.0016 (6)
C19	0.0218 (7)	0.0249 (8)	0.0244 (8)	0.0044 (6)	−0.0008 (6)	0.0032 (6)
C20	0.0206 (7)	0.0212 (8)	0.0209 (7)	−0.0025 (6)	0.0019 (6)	0.0004 (6)
C21	0.0402 (11)	0.0207 (9)	0.0380 (10)	0.0062 (8)	−0.0041 (8)	0.0041 (7)

Geometric parameters (Å, º) top

P1—O1	1.4765 (11)	C9—H9A	0.9300
P1—O2	1.6072 (11)	C10—C11	1.392 (2)
P1—N1	1.6297 (13)	C10—H10A	0.9300
P1—N2	1.6424 (13)	C11—C12	1.390 (2)
O2—C15	1.4114 (17)	C11—C14	1.510 (2)
N1—C1	1.4153 (19)	C12—C13	1.393 (2)
N1—H1N	0.878 (9)	C12—H12A	0.9300
N2—C8	1.4171 (19)	C13—H13A	0.9300
N2—H2N	0.881 (9)	C14—H14A	0.9600
C1—C6	1.390 (2)	C14—H14B	0.9600
C1—C2	1.391 (2)	C14—H14C	0.9600
C2—C3	1.391 (2)	C15—C16	1.382 (2)
C2—H2A	0.9300	C15—C20	1.383 (2)
C3—C4	1.393 (2)	C16—C17	1.392 (2)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.387 (2)	C17—C18	1.398 (2)
C4—C7	1.510 (2)	C17—H17A	0.9300
C5—C6	1.395 (2)	C18—C19	1.388 (2)
C5—H5A	0.9300	C18—C21	1.507 (2)
C6—H6A	0.9300	C19—C20	1.396 (2)
C7—H7A	0.9600	C19—H19A	0.9300
C7—H7B	0.9600	C20—H20A	0.9300
C7—H7C	0.9600	C21—H21A	0.9600
C8—C13	1.394 (2)	C21—H21B	0.9600
C8—C9	1.395 (2)	C21—H21C	0.9600
C9—C10	1.388 (2)

O1—P1—O2	114.12 (6)	C9—C10—C11	121.37 (15)
O1—P1—N1	119.08 (7)	C9—C10—H10A	119.3
O2—P1—N1	96.93 (6)	C11—C10—H10A	119.3
O1—P1—N2	108.07 (6)	C12—C11—C10	117.60 (14)
O2—P1—N2	108.03 (6)	C12—C11—C14	121.38 (15)
N1—P1—N2	109.90 (7)	C10—C11—C14	121.02 (15)
C15—O2—P1	119.58 (9)	C11—C12—C13	121.89 (14)
C1—N1—P1	124.90 (10)	C11—C12—H12A	119.1
C1—N1—H1N	117.2 (13)	C13—C12—H12A	119.1
P1—N1—H1N	117.6 (13)	C12—C13—C8	119.83 (14)
C8—N2—P1	129.74 (10)	C12—C13—H13A	120.1
C8—N2—H2N	116.7 (12)	C8—C13—H13A	120.1
P1—N2—H2N	113.6 (12)	C11—C14—H14A	109.5
C6—C1—C2	119.10 (14)	C11—C14—H14B	109.5
C6—C1—N1	122.17 (13)	H14A—C14—H14B	109.5
C2—C1—N1	118.73 (13)	C11—C14—H14C	109.5
C3—C2—C1	120.27 (15)	H14A—C14—H14C	109.5
C3—C2—H2A	119.9	H14B—C14—H14C	109.5
C1—C2—H2A	119.9	C16—C15—C20	121.99 (14)
C2—C3—C4	121.32 (15)	C16—C15—O2	118.56 (13)
C2—C3—H3A	119.3	C20—C15—O2	119.37 (13)
C4—C3—H3A	119.3	C15—C16—C17	118.52 (14)
C5—C4—C3	117.69 (15)	C15—C16—H16A	120.7
C5—C4—C7	120.50 (15)	C17—C16—H16A	120.7
C3—C4—C7	121.80 (15)	C16—C17—C18	121.35 (15)
C4—C5—C6	121.72 (14)	C16—C17—H17A	119.3
C4—C5—H5A	119.1	C18—C17—H17A	119.3
C6—C5—H5A	119.1	C19—C18—C17	118.22 (15)
C1—C6—C5	119.82 (14)	C19—C18—C21	121.04 (15)
C1—C6—H6A	120.1	C17—C18—C21	120.74 (16)
C5—C6—H6A	120.1	C18—C19—C20	121.53 (15)
C4—C7—H7A	109.5	C18—C19—H19A	119.2
C4—C7—H7B	109.5	C20—C19—H19A	119.2
H7A—C7—H7B	109.5	C15—C20—C19	118.37 (15)
C4—C7—H7C	109.5	C15—C20—H20A	120.8
H7A—C7—H7C	109.5	C19—C20—H20A	120.8
H7B—C7—H7C	109.5	C18—C21—H21A	109.5
C13—C8—C9	118.80 (14)	C18—C21—H21B	109.5
C13—C8—N2	122.85 (13)	H21A—C21—H21B	109.5
C9—C8—N2	118.35 (13)	C18—C21—H21C	109.5
C10—C9—C8	120.49 (14)	H21A—C21—H21C	109.5
C10—C9—H9A	119.8	H21B—C21—H21C	109.5
C8—C9—H9A	119.8

O1—P1—O2—C15	40.60 (12)	C13—C8—C9—C10	−0.4 (2)
N1—P1—O2—C15	166.81 (11)	N2—C8—C9—C10	179.56 (15)
N2—P1—O2—C15	−79.60 (11)	C8—C9—C10—C11	1.1 (3)
O1—P1—N1—C1	−69.46 (14)	C9—C10—C11—C12	−0.6 (2)
O2—P1—N1—C1	167.95 (12)	C9—C10—C11—C14	179.31 (16)
N2—P1—N1—C1	55.89 (14)	C10—C11—C12—C13	−0.5 (2)
O1—P1—N2—C8	−172.64 (13)	C14—C11—C12—C13	179.52 (16)
O2—P1—N2—C8	−48.71 (15)	C11—C12—C13—C8	1.2 (3)
N1—P1—N2—C8	55.93 (15)	C9—C8—C13—C12	−0.7 (2)
P1—N1—C1—C6	15.1 (2)	N2—C8—C13—C12	179.30 (15)
P1—N1—C1—C2	−164.86 (13)	P1—O2—C15—C16	−99.59 (14)
C6—C1—C2—C3	−1.8 (3)	P1—O2—C15—C20	83.48 (16)
N1—C1—C2—C3	178.16 (16)	C20—C15—C16—C17	1.4 (2)
C1—C2—C3—C4	−0.7 (3)	O2—C15—C16—C17	−175.40 (13)
C2—C3—C4—C5	2.1 (3)	C15—C16—C17—C18	−0.9 (2)
C2—C3—C4—C7	−177.02 (17)	C16—C17—C18—C19	−0.5 (2)
C3—C4—C5—C6	−1.0 (2)	C16—C17—C18—C21	179.21 (16)
C7—C4—C5—C6	178.12 (15)	C17—C18—C19—C20	1.4 (3)
C2—C1—C6—C5	2.9 (2)	C21—C18—C19—C20	−178.31 (17)
N1—C1—C6—C5	−177.10 (14)	C16—C15—C20—C19	−0.6 (2)
C4—C5—C6—C1	−1.5 (2)	O2—C15—C20—C19	176.23 (14)
P1—N2—C8—C13	−9.5 (2)	C18—C19—C20—C15	−0.9 (3)
P1—N2—C8—C9	170.57 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.88 (1)	1.93 (1)	2.805 (2)	176 (2)
N2—H2N···O2ⁱⁱ	0.88 (1)	2.21 (1)	3.068 (2)	165 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₂O₂P
M_r	366.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.0977 (6), 14.7657 (6), 9.5155 (4)
β (°)	104.676 (1)
V (Å³)	1916.14 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.40 × 0.26 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.939, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	18737, 5555, 4484
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.107, 1.02
No. of reflections	5555
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.50

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.878 (9)	1.928 (7)	2.805 (2)	176 (2)
N2—H2N···O2ⁱⁱ	0.881 (9)	2.209 (7)	3.068 (2)	165 (2)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

Support of this investigation by the Imam Hossein University is gratefully acknowledged.

References

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