p-Tolyl bis­(o-tolyl­amido)­phosphinate

Sabbaghi, F.; Mancilla Percino, T.; Pourayoubi, M.; Leyva, M.A.

doi:10.1107/S1600536810023512

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1755

doi:10.1107/S1600536810023512

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p-Tolyl bis(o-tolylamido)phosphinate

Fahimeh Sabbaghi,^a ^* Teresa Mancilla Percino,^b Mehrdad Pourayoubi ^c and Marco A. Leyva ^b

^aDepartment of Chemistry, Islamic Azad University-Zanjan Branch, PO Box 49195-467, Zanjan, Iran, ^bDepartamento de Química, Centro de Investigación y de Estudios Avanzados, del Instituto Politécnico Nacional, Apartado Postal 14-740, 07000 México, D.F., México, and ^cDepartment of Chemistry, Ferdowsi University of Mashhad, 91779, Mashhad, Iran
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 21 May 2010; accepted 17 June 2010; online 23 June 2010)

In the title compound, C₂₁H₂₃N₂O₂P, the P atom has a distorted tetrahedral configuration. The O atom of the OC₆H₄-4-CH₃ group and the N atoms show sp² character. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into helical chains parallel to the b axis.

Related literature

For a related structure, see: Pourayoubi et al. (2009 ).

Experimental

Crystal data

C₂₁H₂₃N₂O₂P
M_r = 366.38
Monoclinic, P 2₁ /c
a = 12.157 (3) Å
b = 8.978 (2) Å
c = 18.080 (5) Å
β = 101.569 (1)°
V = 1933.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.6 × 0.54 × 0.47 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.860, T_max = 0.968
23372 measured reflections
4402 independent reflections
3097 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.128
S = 1.06
4402 reflections
257 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.91 (2)	2.02 (2)	2.8963 (19)	161 (2)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2001 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810023512/ng2779sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023512/ng2779Isup2.hkl

checkCIF report

Comment top

In the previous work, the structure determination of p-tolyl bis(p-tolylamido)phosphate (Pourayoubi et al., 2009) has been investigated; we report here on the crystal structure of title compound (Fig. 1). The title compound was synthesized from the reaction of (4-tolyl)-dichlorophosphate with an excess amount of ortho-toluidine (1:4 mole ratio). Single crystals were obtained from CHCl₃/n-C₆H₁₄ at room temperature. Molecular structure of [4-H₃C—C₆H₄O]P(O)[NHC₆H₄-2-CH₃]₂ is shown in Fig. 1. The phosphorus atom has a distorted tetrahedral configuration. The bond angles around P atom are in the range of 96.87 (7)° to 118.95 (8)°. The oxygen atom of OC₆H₄-4-CH₃ moiety and the nitrogen atoms show sp² character (the C15—O2—P1 angle is 124.67 (11)°, the C1—N1—P1 and C8—N2—P1 are 123.77 (12)° and 127.71 (12)°, respectively. In the crystal structure, molecules are linked via N—H···O hydrogen bonds (N1···O1 = 2.8963 (19) Å) into an extended chain (Fig. 2) parallel to the b axis.

Related literature top

For a related structure, see: Pourayoubi et al. (2009).

Experimental top

To a solution of (4-tolyl)-dichlorophosphate (2.250 g, 10 mmol) in 15 ml dry acetonitrile, a solution of ortho-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 CHCl₃/n-C₆H₁₄ at room temperature.

Computing details top

Data collection: COLLECT (Nonius, 2001); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A general view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of N—H···O hydrogen bond.

p-Tolyl bis(o-tolylamido)phosphinate top

Crystal data top

C₂₁H₂₃N₂O₂P	F(000) = 776
M_r = 366.38	D_x = 1.259 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 600 reflections
a = 12.157 (3) Å	θ = 1–14°
b = 8.978 (2) Å	µ = 0.16 mm⁻¹
c = 18.080 (5) Å	T = 293 K
β = 101.569 (1)°	Priem, colourless
V = 1933.3 (8) Å³	0.6 × 0.54 × 0.47 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	4402 independent reflections
Radiation source: Enraf Nonius FR590	3097 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 9 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
CCD rotation images, thick slices scans	h = −15→15
Absorption correction: multi-scan (Blessing, 1995)	k = −10→11
T_min = 0.860, T_max = 0.968	l = −19→23
23372 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0666P)² + 0.2653P] where P = (F_o² + 2F_c²)/3
4402 reflections	(Δ/σ)_max = 0.015
257 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₁H₂₃N₂O₂P	V = 1933.3 (8) Å³
M_r = 366.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.157 (3) Å	µ = 0.16 mm⁻¹
b = 8.978 (2) Å	T = 293 K
c = 18.080 (5) Å	0.6 × 0.54 × 0.47 mm
β = 101.569 (1)°

Data collection top

Nonius KappaCCD diffractometer	4402 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	3097 reflections with I > 2σ(I)
T_min = 0.860, T_max = 0.968	R_int = 0.048
23372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	2 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.18 e Å⁻³
4402 reflections	Δρ_min = −0.36 e Å⁻³
257 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.28763 (13)	0.18689 (18)	0.26516 (10)	0.0359 (4)
C2	0.25191 (16)	0.3029 (2)	0.21582 (11)	0.0464 (4)
H2	0.3036	0.3535	0.1936	0.056*
C3	0.14023 (18)	0.3444 (3)	0.19930 (13)	0.0606 (6)
H3	0.1171	0.4232	0.1665	0.073*
C4	0.06346 (18)	0.2691 (3)	0.23138 (15)	0.0693 (7)
H4	−0.0121	0.2951	0.2197	0.083*
C5	0.09918 (17)	0.1546 (3)	0.28107 (14)	0.0620 (6)
H5	0.0466	0.1044	0.3027	0.074*
C6	0.21099 (15)	0.1116 (2)	0.29999 (11)	0.0446 (4)
C7	0.24895 (19)	−0.0078 (2)	0.35748 (13)	0.0628 (6)
H7A	0.1847	−0.0521	0.3722	0.094*
H7B	0.2969	0.0351	0.401	0.094*
H7C	0.2896	−0.0827	0.3361	0.094*
C8	0.43487 (15)	0.36933 (19)	0.41804 (9)	0.0395 (4)
C9	0.47389 (18)	0.2563 (2)	0.46833 (11)	0.0518 (5)
H9	0.5289	0.1915	0.4585	0.062*
C10	0.4311 (2)	0.2392 (3)	0.53349 (12)	0.0656 (6)
H10	0.4559	0.1615	0.5666	0.079*
C11	0.3524 (2)	0.3374 (3)	0.54873 (13)	0.0687 (7)
H11	0.3252	0.3283	0.5931	0.082*
C12	0.31363 (18)	0.4494 (3)	0.49840 (12)	0.0614 (6)
H12	0.2603	0.5155	0.5095	0.074*
C13	0.35181 (15)	0.4668 (2)	0.43141 (10)	0.0464 (5)
C14	0.3050 (2)	0.5866 (3)	0.37677 (16)	0.0643 (6)
C15	0.71094 (14)	0.1945 (2)	0.36813 (10)	0.0399 (4)
C16	0.76182 (16)	0.1141 (2)	0.43050 (12)	0.0530 (5)
H16	0.7234	0.0378	0.4492	0.064*
C17	0.87118 (17)	0.1486 (3)	0.46506 (13)	0.0607 (6)
H17	0.9056	0.0944	0.5072	0.073*
C18	0.93031 (17)	0.2605 (3)	0.43883 (13)	0.0575 (5)
C19	0.87634 (17)	0.3392 (3)	0.37669 (13)	0.0633 (6)
H19	0.9143	0.4163	0.3583	0.076*
C20	0.76747 (16)	0.3071 (2)	0.34082 (12)	0.0539 (5)
H20	0.7331	0.3613	0.2987	0.065*
C21	1.0505 (2)	0.2947 (4)	0.47617 (17)	0.0897 (9)
H21A	1.0534	0.3242	0.5276	0.135*
H21B	1.0784	0.3741	0.4495	0.135*
H21C	1.0959	0.2075	0.4751	0.135*
N1	0.40296 (12)	0.14475 (16)	0.28185 (9)	0.0387 (3)
N2	0.48102 (13)	0.38993 (16)	0.35183 (8)	0.0393 (3)
O1	0.53434 (10)	0.33484 (13)	0.22624 (7)	0.0420 (3)
O2	0.60148 (10)	0.15191 (13)	0.33463 (7)	0.0444 (3)
P1	0.50634 (4)	0.26305 (4)	0.29312 (2)	0.03385 (15)
H1	0.4230 (17)	0.0477 (18)	0.2912 (12)	0.062 (6)*
H21	0.4928 (17)	0.4862 (18)	0.3421 (12)	0.061 (6)*
H14C	0.267 (3)	0.548 (3)	0.3309 (19)	0.104 (10)*
H14B	0.249 (3)	0.645 (4)	0.3955 (18)	0.123 (11)*
H14A	0.363 (3)	0.660 (3)	0.3641 (17)	0.105 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0343 (9)	0.0320 (9)	0.0410 (9)	−0.0007 (7)	0.0063 (7)	−0.0066 (7)
C2	0.0451 (11)	0.0446 (10)	0.0496 (11)	0.0036 (8)	0.0099 (9)	0.0016 (8)
C3	0.0508 (12)	0.0606 (13)	0.0673 (13)	0.0155 (10)	0.0046 (10)	0.0094 (11)
C4	0.0381 (11)	0.0708 (15)	0.0969 (19)	0.0124 (10)	0.0085 (12)	0.0035 (13)
C5	0.0429 (12)	0.0608 (13)	0.0875 (16)	−0.0049 (10)	0.0255 (11)	−0.0025 (12)
C6	0.0434 (10)	0.0400 (10)	0.0524 (11)	−0.0032 (8)	0.0142 (8)	−0.0028 (8)
C7	0.0634 (13)	0.0583 (13)	0.0724 (14)	−0.0046 (11)	0.0272 (11)	0.0159 (11)
C8	0.0440 (10)	0.0391 (9)	0.0351 (9)	−0.0131 (7)	0.0074 (7)	−0.0069 (7)
C9	0.0580 (12)	0.0516 (12)	0.0446 (11)	−0.0084 (9)	0.0072 (9)	0.0031 (9)
C10	0.0774 (16)	0.0723 (15)	0.0447 (12)	−0.0274 (13)	0.0066 (11)	0.0083 (10)
C11	0.0781 (16)	0.0866 (17)	0.0469 (12)	−0.0379 (14)	0.0255 (11)	−0.0122 (12)
C12	0.0569 (12)	0.0702 (15)	0.0627 (13)	−0.0206 (11)	0.0254 (10)	−0.0215 (12)
C13	0.0456 (10)	0.0465 (11)	0.0488 (10)	−0.0140 (8)	0.0137 (8)	−0.0136 (8)
C14	0.0639 (15)	0.0566 (14)	0.0739 (16)	0.0124 (12)	0.0176 (13)	−0.0040 (12)
C15	0.0335 (9)	0.0392 (10)	0.0470 (10)	0.0002 (7)	0.0080 (8)	−0.0031 (8)
C16	0.0428 (11)	0.0542 (12)	0.0610 (12)	0.0002 (9)	0.0085 (9)	0.0113 (10)
C17	0.0464 (12)	0.0712 (14)	0.0597 (13)	0.0073 (10)	−0.0009 (10)	0.0060 (11)
C18	0.0394 (11)	0.0678 (14)	0.0626 (13)	−0.0017 (9)	0.0039 (10)	−0.0080 (11)
C19	0.0461 (12)	0.0682 (14)	0.0757 (15)	−0.0163 (10)	0.0125 (11)	0.0062 (12)
C20	0.0420 (11)	0.0583 (12)	0.0592 (12)	−0.0062 (9)	0.0052 (9)	0.0133 (10)
C21	0.0464 (14)	0.108 (2)	0.105 (2)	−0.0113 (14)	−0.0079 (14)	−0.0065 (18)
N1	0.0352 (8)	0.0277 (7)	0.0527 (9)	0.0005 (6)	0.0075 (6)	−0.0013 (6)
N2	0.0519 (9)	0.0282 (8)	0.0399 (8)	−0.0047 (6)	0.0144 (7)	−0.0016 (6)
O1	0.0477 (7)	0.0385 (7)	0.0428 (7)	−0.0021 (5)	0.0159 (5)	0.0007 (5)
O2	0.0335 (6)	0.0342 (6)	0.0627 (8)	−0.0016 (5)	0.0025 (6)	0.0045 (6)
P1	0.0341 (2)	0.0287 (2)	0.0391 (3)	−0.00105 (17)	0.00834 (18)	−0.00115 (17)

Geometric parameters (Å, º) top

C1—C2	1.383 (3)	C13—C14	1.494 (3)
C1—C6	1.399 (2)	C14—H14C	0.93 (3)
C1—N1	1.425 (2)	C14—H14B	0.97 (3)
C2—C3	1.381 (3)	C14—H14A	1.02 (3)
C2—H2	0.93	C15—C20	1.369 (3)
C3—C4	1.372 (3)	C15—C16	1.377 (3)
C3—H3	0.93	C15—O2	1.400 (2)
C4—C5	1.377 (3)	C16—C17	1.386 (3)
C4—H4	0.93	C16—H16	0.93
C5—C6	1.388 (3)	C17—C18	1.374 (3)
C5—H5	0.93	C17—H17	0.93
C6—C7	1.500 (3)	C18—C19	1.377 (3)
C7—H7A	0.96	C18—C21	1.513 (3)
C7—H7B	0.96	C19—C20	1.382 (3)
C7—H7C	0.96	C19—H19	0.93
C8—C9	1.382 (3)	C20—H20	0.93
C8—C13	1.393 (3)	C21—H21A	0.96
C8—N2	1.432 (2)	C21—H21B	0.96
C9—C10	1.388 (3)	C21—H21C	0.96
C9—H9	0.93	N1—P1	1.6268 (15)
C10—C11	1.369 (4)	N1—H1	0.911 (15)
C10—H10	0.93	N2—P1	1.6279 (15)
C11—C12	1.375 (3)	N2—H21	0.899 (15)
C11—H11	0.93	O1—P1	1.4692 (12)
C12—C13	1.390 (3)	O2—P1	1.5964 (13)
C12—H12	0.93

C2—C1—C6	120.19 (16)	C13—C14—H14B	111.0 (19)
C2—C1—N1	120.32 (15)	H14C—C14—H14B	105 (3)
C6—C1—N1	119.48 (16)	C13—C14—H14A	114.9 (17)
C3—C2—C1	120.67 (18)	H14C—C14—H14A	106 (2)
C3—C2—H2	119.7	H14B—C14—H14A	107 (2)
C1—C2—H2	119.7	C20—C15—C16	120.46 (17)
C4—C3—C2	119.9 (2)	C20—C15—O2	123.22 (17)
C4—C3—H3	120.1	C16—C15—O2	116.30 (16)
C2—C3—H3	120.1	C15—C16—C17	119.01 (19)
C3—C4—C5	119.4 (2)	C15—C16—H16	120.5
C3—C4—H4	120.3	C17—C16—H16	120.5
C5—C4—H4	120.3	C18—C17—C16	121.9 (2)
C4—C5—C6	122.25 (19)	C18—C17—H17	119
C4—C5—H5	118.9	C16—C17—H17	119
C6—C5—H5	118.9	C17—C18—C19	117.39 (19)
C5—C6—C1	117.52 (18)	C17—C18—C21	121.3 (2)
C5—C6—C7	121.31 (18)	C19—C18—C21	121.3 (2)
C1—C6—C7	121.15 (17)	C18—C19—C20	122.0 (2)
C6—C7—H7A	109.5	C18—C19—H19	119
C6—C7—H7B	109.5	C20—C19—H19	119
H7A—C7—H7B	109.5	C15—C20—C19	119.2 (2)
C6—C7—H7C	109.5	C15—C20—H20	120.4
H7A—C7—H7C	109.5	C19—C20—H20	120.4
H7B—C7—H7C	109.5	C18—C21—H21A	109.5
C9—C8—C13	120.81 (18)	C18—C21—H21B	109.5
C9—C8—N2	120.30 (17)	H21A—C21—H21B	109.5
C13—C8—N2	118.87 (16)	C18—C21—H21C	109.5
C8—C9—C10	120.1 (2)	H21A—C21—H21C	109.5
C8—C9—H9	119.9	H21B—C21—H21C	109.5
C10—C9—H9	119.9	C1—N1—P1	123.77 (12)
C11—C10—C9	119.7 (2)	C1—N1—H1	120.6 (13)
C11—C10—H10	120.1	P1—N1—H1	115.4 (13)
C9—C10—H10	120.1	C8—N2—P1	127.71 (12)
C10—C11—C12	119.9 (2)	C8—N2—H21	113.0 (14)
C10—C11—H11	120.1	P1—N2—H21	119.2 (14)
C12—C11—H11	120.1	C15—O2—P1	124.67 (11)
C11—C12—C13	121.9 (2)	O1—P1—O2	113.30 (7)
C11—C12—H12	119	O1—P1—N1	118.95 (8)
C13—C12—H12	119	O2—P1—N1	96.87 (7)
C12—C13—C8	117.46 (19)	O1—P1—N2	109.57 (7)
C12—C13—C14	120.5 (2)	O2—P1—N2	110.16 (8)
C8—C13—C14	122.06 (18)	N1—P1—N2	107.23 (7)
C13—C14—H14C	112.0 (18)

C6—C1—C2—C3	−1.1 (3)	C15—C16—C17—C18	−0.1 (3)
N1—C1—C2—C3	179.94 (17)	C16—C17—C18—C19	0.6 (3)
C1—C2—C3—C4	−0.7 (3)	C16—C17—C18—C21	−178.7 (2)
C2—C3—C4—C5	1.3 (4)	C17—C18—C19—C20	−0.8 (3)
C3—C4—C5—C6	−0.2 (4)	C21—C18—C19—C20	178.5 (2)
C4—C5—C6—C1	−1.5 (3)	C16—C15—C20—C19	0.0 (3)
C4—C5—C6—C7	176.6 (2)	O2—C15—C20—C19	−178.57 (19)
C2—C1—C6—C5	2.1 (3)	C18—C19—C20—C15	0.5 (3)
N1—C1—C6—C5	−178.90 (17)	C2—C1—N1—P1	39.1 (2)
C2—C1—C6—C7	−175.95 (18)	C6—C1—N1—P1	−139.85 (15)
N1—C1—C6—C7	3.0 (3)	C9—C8—N2—P1	45.5 (2)
C13—C8—C9—C10	−0.6 (3)	C13—C8—N2—P1	−135.66 (15)
N2—C8—C9—C10	178.22 (17)	C20—C15—O2—P1	−33.5 (2)
C8—C9—C10—C11	−1.8 (3)	C16—C15—O2—P1	147.94 (14)
C9—C10—C11—C12	2.0 (3)	C15—O2—P1—O1	62.76 (15)
C10—C11—C12—C13	0.2 (3)	C15—O2—P1—N1	−171.60 (13)
C11—C12—C13—C8	−2.4 (3)	C15—O2—P1—N2	−60.38 (15)
C11—C12—C13—C14	177.9 (2)	C1—N1—P1—O1	−75.73 (15)
C9—C8—C13—C12	2.6 (3)	C1—N1—P1—O2	162.81 (14)
N2—C8—C13—C12	−176.18 (16)	C1—N1—P1—N2	49.18 (16)
C9—C8—C13—C14	−177.7 (2)	C8—N2—P1—O1	169.91 (14)
N2—C8—C13—C14	3.5 (3)	C8—N2—P1—O2	−64.80 (17)
C20—C15—C16—C17	−0.2 (3)	C8—N2—P1—N1	39.51 (17)
O2—C15—C16—C17	178.44 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.91 (2)	2.02 (2)	2.8963 (19)	161 (2)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₂O₂P
M_r	366.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.157 (3), 8.978 (2), 18.080 (5)
β (°)	101.569 (1)
V (Å³)	1933.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.16
Crystal size (mm)	0.6 × 0.54 × 0.47

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.860, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	23372, 4402, 3097
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.128, 1.06
No. of reflections	4402
No. of parameters	257
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)	0.18, −0.36

Computer programs: COLLECT (Nonius, 2001), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.911 (15)	2.021 (17)	2.8963 (19)	160.5 (19)

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

Support of this investigation by Islamic Azad University-Zanjan Branch is gratefully acknowledged.

References

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