rac-Phenyl (benzylamido)(p-tolyl­amido)­phosphinate

Pourayoubi, M.; Karimi Ahmadabad, F.; Nečas, M.

doi:10.1107/S1600536811034465

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2523

doi:10.1107/S1600536811034465

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rac-Phenyl (benzylamido)(p-tolylamido)phosphinate

Mehrdad Pourayoubi,^a ^* Fatemeh Karimi Ahmadabad ^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 6 August 2011; accepted 22 August 2011; online 31 August 2011)

The title compound, C₂₀H₂₁N₂O₂P, was synthesized from (RS)-(C₆H₅O)P(O)Cl(NHC₆H₄-p-CH₃) and benzylamine. The product crystallizes as a racemate in a polar space group. The phosphorus atom has a distorted tetrahedral configuration: the bond angles at the P atom are in the range 103.2 (1)–118.4 (1)°. The P—N(benzylamido) bond [1.615 (2) Å] is slightly shorter than the P—N(p-tolylamido) bond [1.630 (2) Å]. Both N—H groups adopt an anti orientation relative to the phosphoryl group. In the crystal, the adjacent molecules are linked via N—H⋯O hydrogen bonds, forming R₂²(8) rings, into a one-dimensional arrangement parallel to the x axis.

Related literature

For a related mixed-amido phosphinate derivative and its molecular geometry, see: Sabbaghi et al. (2011 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₀H₂₁N₂O₂P
M_r = 352.36
Orthorhombic, P c a 2₁
a = 9.6986 (5) Å
b = 13.0751 (6) Å
c = 14.3446 (5) Å
V = 1819.04 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.30 × 0.30 × 0.10 mm

Data collection

Xcalibur, Sapphire2, large Be window diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.785, T_max = 1.000
20413 measured reflections
3200 independent reflections
2823 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.099
S = 1.00
3200 reflections
233 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.29 e Å⁻³
Absolute structure: Flack (1983 ), 1526 Friedel pairs
Flack parameter: 0.01 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.76 (3)	2.43 (3)	3.127 (3)	153 (3)
N2—H2N⋯O2ⁱ	0.86 (3)	1.91 (3)	2.761 (3)	176 (3)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+2, z]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S1600536811034465/ld2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034465/ld2023Isup2.hkl

checkCIF report

Comment top

In continuation of the previous works on synthesis and structure determination of mixed-amido phosphinates with common formula (RO)(NR¹R²)(NR³R⁴)P(O) (Sabbaghi et al., 2011; and the related reference cited therein), the structure of the title molecule, [C₆H₅O][4-CH₃C₆H₄NH][C₆H₅CH₂NH]PO (Fig. 1), is reported here.

Single crystals were obtained from CHCl₃/CH₃CN at room temperature.

The P═O (1.4679 (17) Å), P—O (1.6250 (17) Å), P—N (1.615 (2) Å & 1.630 (2) Å) and C—O (1.400 (3) Å) bond lengths and the P—N—C (120.54 (18)° & 125.18 (18)°) and P—O—C (120.90 (14)°) bond angles are within the expected values (Sabbaghi et al., 2011).

The phosphorus atom has a distorted tetrahedral P(═O)(O)(N)(N) environment. The bond angles at the P atom are in the range from 103.17 (9)° [for the O2—P1—O1 angle] to 118.39 (11)° [for the O2—P1—N2 angle].

In the crystal structure, neighbouring molecules are H-bonded via N—H···O(P) hydrogen bonds, building R₂²(8) rings (Bernstein et al., 1995), in a linear arrangement parallel to [100], Table 1, Fig. 2.

Related literature top

For a related mixed-amido phosphinate and its molecular geometry, see: Sabbaghi et al. (2011). For graph-set notations, see: Bernstein et al. (1995).

Experimental top

To a solution of (C₆H₅O)(4-CH₃C₆H₄NH)P(O)Cl (2.286 mmol) in chloroform, a solution of benzylamine (4.572 mmol) in chloroform was added at 273 K. After stirring for 5 h, the solvent was removed and the obtained solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in CH₃CN/CHCl₃ after slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (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. An ORTEP style plot and atom labeling scheme for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of an arbitrary radius.
	Fig. 2. Part of the crystal packing of the title compound with the hydrogen bonds shown as dotted lines (the C—H hydrogen atoms are omitted for clarity).

rac-Phenyl (benzylamido)(p-tolylamido)phosphinate top

Crystal data top

C₂₀H₂₁N₂O₂P	D_x = 1.287 Mg m⁻³
M_r = 352.36	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pca2₁	Cell parameters from 10547 reflections
a = 9.6986 (5) Å	θ = 3.0–27.2°
b = 13.0751 (6) Å	µ = 0.17 mm⁻¹
c = 14.3446 (5) Å	T = 120 K
V = 1819.04 (14) Å³	Plate, colorless
Z = 4	0.30 × 0.30 × 0.10 mm
F(000) = 744

Data collection top

Xcalibur, Sapphire2, large Be window diffractometer	3200 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2823 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
ω scan	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→15
T_min = 0.785, T_max = 1.000	l = −17→17
20413 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.073P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
3200 reflections	Δρ_max = 0.51 e Å⁻³
233 parameters	Δρ_min = −0.29 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1523 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (10)

Crystal data top

C₂₀H₂₁N₂O₂P	V = 1819.04 (14) Å³
M_r = 352.36	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 9.6986 (5) Å	µ = 0.17 mm⁻¹
b = 13.0751 (6) Å	T = 120 K
c = 14.3446 (5) Å	0.30 × 0.30 × 0.10 mm

Data collection top

Xcalibur, Sapphire2, large Be window diffractometer	3200 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2823 reflections with I > 2σ(I)
T_min = 0.785, T_max = 1.000	R_int = 0.047
20413 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	Δρ_max = 0.51 e Å⁻³
S = 1.00	Δρ_min = −0.29 e Å⁻³
3200 reflections	Absolute structure: Flack (1983), 1523 Friedel pairs
233 parameters	Absolute structure parameter: 0.01 (10)
1 restraint

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	0.91905 (5)	0.99930 (4)	0.56899 (5)	0.01847 (16)
O1	0.84602 (16)	1.07673 (12)	0.64256 (11)	0.0217 (4)
O2	0.80162 (17)	0.94641 (13)	0.52605 (12)	0.0247 (4)
N1	1.0250 (2)	0.92421 (16)	0.62255 (15)	0.0241 (5)
H1N	1.098 (3)	0.944 (2)	0.630 (2)	0.029*
N2	1.0197 (2)	1.06729 (15)	0.50236 (15)	0.0217 (5)
H2N	1.107 (3)	1.062 (2)	0.5071 (19)	0.026*
C1	0.9250 (2)	1.1424 (2)	0.69810 (16)	0.0207 (6)
C2	0.9809 (3)	1.1052 (2)	0.78124 (17)	0.0264 (6)
H2C	0.9699	1.0356	0.7987	0.032*
C3	1.0533 (3)	1.1733 (2)	0.83765 (18)	0.0297 (6)
H3A	1.0940	1.1494	0.8938	0.036*
C4	1.0667 (3)	1.2738 (2)	0.81375 (18)	0.0290 (6)
H4A	1.1156	1.3192	0.8535	0.035*
C5	1.0088 (3)	1.3098 (2)	0.73111 (18)	0.0283 (6)
H5A	1.0182	1.3798	0.7143	0.034*
C6	0.9375 (3)	1.2432 (2)	0.67366 (17)	0.0249 (6)
H6A	0.8974	1.2674	0.6174	0.030*
C7	0.9737 (3)	0.83908 (19)	0.67821 (18)	0.0273 (6)
H7A	0.8801	0.8564	0.7006	0.033*
H7B	1.0336	0.8315	0.7337	0.033*
C8	0.9671 (3)	0.73740 (18)	0.62858 (16)	0.0225 (5)
C9	0.8580 (3)	0.6727 (2)	0.6440 (2)	0.0360 (7)
H9A	0.7840	0.6945	0.6826	0.043*
C10	0.8539 (4)	0.5761 (2)	0.6042 (2)	0.0503 (9)
H10A	0.7787	0.5316	0.6167	0.060*
C11	0.9596 (4)	0.5448 (2)	0.54621 (18)	0.0436 (8)
H11A	0.9573	0.4789	0.5184	0.052*
C12	1.0667 (3)	0.6091 (2)	0.52932 (19)	0.0368 (7)
H12A	1.1394	0.5876	0.4895	0.044*
C13	1.0716 (3)	0.70547 (18)	0.5693 (2)	0.0282 (5)
H13A	1.1467	0.7498	0.5561	0.034*
C14	0.9794 (3)	1.15603 (17)	0.45273 (16)	0.0196 (5)
C15	1.0762 (3)	1.23182 (19)	0.43674 (17)	0.0246 (5)
H15A	1.1680	1.2239	0.4588	0.030*
C16	1.0383 (3)	1.3201 (2)	0.38799 (19)	0.0296 (6)
H16A	1.1061	1.3707	0.3753	0.036*
C17	0.9042 (3)	1.33547 (18)	0.35774 (16)	0.0258 (6)
C18	0.8104 (3)	1.25870 (19)	0.37405 (16)	0.0249 (6)
H18A	0.7182	1.2670	0.3530	0.030*
C19	0.8467 (3)	1.16882 (19)	0.42071 (16)	0.0229 (5)
H19A	0.7799	1.1167	0.4303	0.027*
C20	0.8653 (3)	1.4309 (2)	0.3061 (2)	0.0364 (7)
H20A	0.7646	1.4369	0.3040	0.055*
H20B	0.9017	1.4276	0.2424	0.055*
H20C	0.9041	1.4905	0.3381	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0170 (3)	0.0230 (3)	0.0154 (3)	−0.0002 (3)	0.0001 (3)	0.0003 (2)
O1	0.0207 (9)	0.0288 (9)	0.0155 (8)	0.0002 (7)	−0.0003 (7)	−0.0013 (7)
O2	0.0199 (9)	0.0295 (10)	0.0247 (8)	−0.0025 (7)	−0.0001 (7)	−0.0008 (7)
N1	0.0185 (11)	0.0276 (12)	0.0261 (12)	−0.0036 (10)	−0.0027 (10)	0.0003 (9)
N2	0.0153 (11)	0.0287 (11)	0.0211 (10)	0.0021 (9)	−0.0001 (9)	0.0026 (9)
C1	0.0165 (13)	0.0302 (14)	0.0154 (12)	−0.0025 (10)	0.0021 (9)	−0.0065 (10)
C2	0.0320 (15)	0.0292 (13)	0.0180 (11)	0.0010 (11)	−0.0026 (11)	0.0026 (11)
C3	0.0307 (15)	0.0421 (16)	0.0163 (12)	0.0023 (13)	−0.0032 (11)	−0.0008 (12)
C4	0.0274 (14)	0.0378 (15)	0.0217 (13)	−0.0048 (12)	−0.0014 (11)	−0.0077 (11)
C5	0.0308 (16)	0.0282 (14)	0.0260 (15)	−0.0039 (12)	0.0044 (12)	−0.0031 (12)
C6	0.0239 (14)	0.0340 (14)	0.0167 (11)	0.0031 (11)	0.0007 (10)	0.0015 (11)
C7	0.0368 (17)	0.0260 (14)	0.0190 (13)	0.0026 (12)	−0.0008 (12)	0.0046 (11)
C8	0.0241 (13)	0.0262 (13)	0.0173 (12)	0.0033 (11)	−0.0028 (10)	0.0056 (10)
C9	0.0355 (16)	0.0454 (16)	0.0272 (14)	−0.0088 (13)	0.0049 (12)	−0.0043 (13)
C10	0.066 (2)	0.0461 (18)	0.0387 (16)	−0.0296 (17)	0.0033 (17)	−0.0012 (14)
C11	0.083 (2)	0.0280 (14)	0.0199 (14)	−0.0073 (16)	−0.0028 (14)	−0.0025 (11)
C12	0.054 (2)	0.0357 (15)	0.0201 (13)	0.0115 (14)	0.0042 (13)	0.0011 (11)
C13	0.0289 (14)	0.0316 (13)	0.0240 (12)	0.0016 (10)	0.0020 (12)	0.0081 (13)
C14	0.0214 (14)	0.0257 (13)	0.0118 (12)	0.0031 (11)	0.0044 (10)	−0.0037 (10)
C15	0.0229 (14)	0.0327 (13)	0.0184 (12)	0.0010 (11)	−0.0016 (10)	−0.0015 (11)
C16	0.0361 (17)	0.0274 (13)	0.0254 (13)	−0.0051 (12)	0.0057 (12)	−0.0009 (11)
C17	0.0368 (16)	0.0279 (14)	0.0128 (12)	0.0071 (11)	0.0029 (10)	−0.0027 (10)
C18	0.0252 (14)	0.0341 (14)	0.0154 (12)	0.0058 (11)	0.0008 (10)	−0.0026 (11)
C19	0.0237 (14)	0.0295 (13)	0.0154 (11)	0.0002 (11)	0.0010 (10)	−0.0004 (10)
C20	0.0481 (18)	0.0310 (14)	0.0302 (14)	0.0037 (14)	0.0008 (13)	0.0023 (12)

Geometric parameters (Å, º) top

P1—O2	1.4679 (17)	C8—C13	1.387 (4)
P1—N1	1.615 (2)	C9—C10	1.386 (4)
P1—O1	1.6250 (17)	C9—H9A	0.9500
P1—N2	1.630 (2)	C10—C11	1.382 (4)
O1—C1	1.400 (3)	C10—H10A	0.9500
N1—C7	1.457 (3)	C11—C12	1.358 (4)
N1—H1N	0.76 (3)	C11—H11A	0.9500
N2—C14	1.416 (3)	C12—C13	1.385 (4)
N2—H2N	0.86 (3)	C12—H12A	0.9500
C1—C6	1.369 (4)	C13—H13A	0.9500
C1—C2	1.398 (4)	C14—C19	1.377 (4)
C2—C3	1.393 (4)	C14—C15	1.385 (3)
C2—H2C	0.9500	C15—C16	1.399 (4)
C3—C4	1.364 (4)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.386 (4)
C4—C5	1.394 (4)	C16—H16A	0.9500
C4—H4A	0.9500	C17—C18	1.375 (4)
C5—C6	1.384 (4)	C17—C20	1.499 (3)
C5—H5A	0.9500	C18—C19	1.397 (4)
C6—H6A	0.9500	C18—H18A	0.9500
C7—C8	1.510 (4)	C19—H19A	0.9500
C7—H7A	0.9900	C20—H20A	0.9800
C7—H7B	0.9900	C20—H20B	0.9800
C8—C9	1.373 (4)	C20—H20C	0.9800

O2—P1—N1	114.00 (11)	C8—C9—C10	121.1 (3)
O2—P1—O1	103.17 (9)	C8—C9—H9A	119.4
N1—P1—O1	110.30 (11)	C10—C9—H9A	119.4
O2—P1—N2	118.39 (11)	C11—C10—C9	119.8 (3)
N1—P1—N2	103.28 (11)	C11—C10—H10A	120.1
O1—P1—N2	107.58 (10)	C9—C10—H10A	120.1
C1—O1—P1	120.90 (14)	C12—C11—C10	119.4 (3)
C7—N1—P1	120.54 (18)	C12—C11—H11A	120.3
C7—N1—H1N	120 (2)	C10—C11—H11A	120.3
P1—N1—H1N	117 (2)	C11—C12—C13	121.0 (3)
C14—N2—P1	125.18 (18)	C11—C12—H12A	119.5
C14—N2—H2N	112.1 (18)	C13—C12—H12A	119.5
P1—N2—H2N	120.5 (19)	C12—C13—C8	120.2 (2)
C6—C1—C2	121.3 (2)	C12—C13—H13A	119.9
C6—C1—O1	119.6 (2)	C8—C13—H13A	119.9
C2—C1—O1	118.9 (2)	C19—C14—C15	119.5 (2)
C3—C2—C1	117.9 (2)	C19—C14—N2	121.7 (2)
C3—C2—H2C	121.1	C15—C14—N2	118.8 (2)
C1—C2—H2C	121.1	C14—C15—C16	119.7 (2)
C4—C3—C2	121.2 (2)	C14—C15—H15A	120.2
C4—C3—H3A	119.4	C16—C15—H15A	120.2
C2—C3—H3A	119.4	C17—C16—C15	121.5 (2)
C3—C4—C5	120.1 (3)	C17—C16—H16A	119.2
C3—C4—H4A	120.0	C15—C16—H16A	119.2
C5—C4—H4A	120.0	C18—C17—C16	117.5 (2)
C6—C5—C4	119.7 (2)	C18—C17—C20	121.7 (2)
C6—C5—H5A	120.2	C16—C17—C20	120.8 (2)
C4—C5—H5A	120.2	C17—C18—C19	121.9 (2)
C1—C6—C5	119.8 (2)	C17—C18—H18A	119.0
C1—C6—H6A	120.1	C19—C18—H18A	119.0
C5—C6—H6A	120.1	C14—C19—C18	119.8 (2)
N1—C7—C8	115.4 (2)	C14—C19—H19A	120.1
N1—C7—H7A	108.4	C18—C19—H19A	120.1
C8—C7—H7A	108.4	C17—C20—H20A	109.5
N1—C7—H7B	108.4	C17—C20—H20B	109.5
C8—C7—H7B	108.4	H20A—C20—H20B	109.5
H7A—C7—H7B	107.5	C17—C20—H20C	109.5
C9—C8—C13	118.5 (2)	H20A—C20—H20C	109.5
C9—C8—C7	119.9 (2)	H20B—C20—H20C	109.5
C13—C8—C7	121.6 (2)

O2—P1—O1—C1	−179.64 (16)	N1—C7—C8—C13	41.2 (3)
N1—P1—O1—C1	58.23 (19)	C13—C8—C9—C10	2.3 (4)
N2—P1—O1—C1	−53.74 (19)	C7—C8—C9—C10	−175.7 (3)
O2—P1—N1—C7	−40.2 (2)	C8—C9—C10—C11	−1.5 (5)
O1—P1—N1—C7	75.3 (2)	C9—C10—C11—C12	0.3 (5)
N2—P1—N1—C7	−169.97 (18)	C10—C11—C12—C13	0.0 (4)
O2—P1—N2—C14	64.2 (2)	C11—C12—C13—C8	0.8 (4)
N1—P1—N2—C14	−168.78 (18)	C9—C8—C13—C12	−1.9 (4)
O1—P1—N2—C14	−52.1 (2)	C7—C8—C13—C12	176.0 (2)
P1—O1—C1—C6	100.9 (2)	P1—N2—C14—C19	−30.3 (3)
P1—O1—C1—C2	−83.8 (2)	P1—N2—C14—C15	149.3 (2)
C6—C1—C2—C3	−1.6 (4)	C19—C14—C15—C16	−0.3 (4)
O1—C1—C2—C3	−176.8 (2)	N2—C14—C15—C16	−179.9 (2)
C1—C2—C3—C4	1.4 (4)	C14—C15—C16—C17	2.2 (4)
C2—C3—C4—C5	−0.7 (4)	C15—C16—C17—C18	−2.6 (4)
C3—C4—C5—C6	0.1 (4)	C15—C16—C17—C20	179.6 (2)
C2—C1—C6—C5	1.1 (4)	C16—C17—C18—C19	1.1 (3)
O1—C1—C6—C5	176.3 (2)	C20—C17—C18—C19	178.9 (2)
C4—C5—C6—C1	−0.3 (4)	C15—C14—C19—C18	−1.2 (3)
P1—N1—C7—C8	94.9 (3)	N2—C14—C19—C18	178.4 (2)
N1—C7—C8—C9	−140.9 (3)	C17—C18—C19—C14	0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.76 (3)	2.43 (3)	3.127 (3)	153 (3)
N2—H2N···O2ⁱ	0.86 (3)	1.91 (3)	2.761 (3)	176 (3)

Symmetry code: (i) x+1/2, −y+2, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₁N₂O₂P
M_r	352.36
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	120
a, b, c (Å)	9.6986 (5), 13.0751 (6), 14.3446 (5)
V (Å³)	1819.04 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Xcalibur, Sapphire2, large Be window diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.785, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	20413, 3200, 2823
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.099, 1.00
No. of reflections	3200
No. of parameters	233
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.29
Absolute structure	Flack (1983), 1523 Friedel pairs
Absolute structure parameter	0.01 (10)

Computer programs: CrysAlis PRO (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
N1—H1N···O1ⁱ	0.76 (3)	2.43 (3)	3.127 (3)	153 (3)
N2—H2N···O2ⁱ	0.86 (3)	1.91 (3)	2.761 (3)	176 (3)

Symmetry code: (i) x+1/2, −y+2, z.

Acknowledgements

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

References

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