Diphenyl [(S)-1-phenylpropanamido]-phosphate.

The title compound, C(21)H(22)NO(3)P, was synthesized from the reaction of (C(6)H(5)O)(2)P(O)(Cl) and S-1-phenyl-propyl-amine (1:2 mole ratio) at 273 K, followed by removal of the S-1-phenyl-propyl-amine hydro-chloride by-product by dissolving in H(2)O. The P atom is located in a distorted tetra-hedral environment. The bond angles at the P atom vary from 99.51 (12) to 116.68 (12)°. The sp(2) character of the N atom is reflected by the C-N-P angle [120.9 (2)°]. The P=O group and the N-H unit adopt an anti orientation with respect to one another. In the crystal, adjacent mol-ecules are linked via N-H⋯O(P) hydrogen bonds into a one-dimensional arrangement running parallel to the a axis.

Related literature

For background literature on phon class="Chemical">spho­ramidates having a <class="Chemical">pan> class="Chemical">span class="Chemical">C(=O)NHP(=O) skeleton, and the <spn>an class="Chemical">hydrogen-bond patterns and strengths, see: Toghraee et al. (2011 ▶); Pourayoubi et al. (2011 ▶). For a related phospho­ramidate with a P(=O)(O)2(N) skeleton, and its bond lengths and angles, see: Pourayoubi et al. (2010 ▶).

Experimental

Crystal data

<n class="Chemical">span class="Chemical">C21H22NO3Ppan>>

M = 367.37

Orthorhombic,

a = 5.4853 (3) Å

b = 8.1450 (11) Å

c = 41.162 (4) Å

V = 1839.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 120 K

0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector

Absorption correction: multi-scan (CrysAlis <n class="Chemical">span class="Disease">REDn>; Oxford Diffraction, 2009 ▶) T min = 0.981, T max = 1.000

4914 measu<n class="Chemical">span class="Disease">redpan>> reflections

3000 independent reflections

2404 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.089

S = 1.07

3000 reflections

239 parameters

1 restraint

<n class="Chemical">span class="Disease">H atomspan>> treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.42 e Å−3

Absolute structure: Flack (1983 ▶), 1052 Friedel pairs

Flack parameter: −0.09 (14)

Data collection: CrysAlis <n class="Chemical">spanclass="Chemical">pan> class="Disease">CCDn> (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis <spn>an class="Disease">RED (Oxford Diffraction, 2009 ▶); data <span class="Disease">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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536811034507/dn2713sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034507/dn2713Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H22NO3P	F(000) = 776
Mr = 367.37	Dx = 1.327 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1550 reflections
a = 5.4853 (3) Å	θ = 3.2–27.6°
b = 8.1450 (11) Å	µ = 0.17 mm−1
c = 41.162 (4) Å	T = 120 K
V = 1839.0 (3) Å3	Plate, colorless
Z = 4	0.40 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	3000 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2404 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scan	h = −5→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −9→5
Tmin = 0.981, Tmax = 1.000	l = −48→48
4914 measured reflections

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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0325P)2 + 0.0316P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3000 reflections	Δρmax = 0.41 e Å−3
239 parameters	Δρmin = −0.42 e Å−3
1 restraint	Absolute structure: Flack (1983), 1052 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.09 (14)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

	x	y	z	Uiso*/Ueq
P1	1.02848 (15)	0.21930 (11)	0.13952 (2)	0.0144 (2)
O1	1.0319 (4)	0.2594 (3)	0.10191 (4)	0.0190 (6)
O2	0.9231 (4)	0.3876 (2)	0.15288 (5)	0.0159 (5)
O3	1.2652 (4)	0.1671 (2)	0.15233 (5)	0.0168 (6)
N1	0.8109 (5)	0.0886 (3)	0.14460 (7)	0.0122 (6)
H1	0.664 (2)	0.118 (3)	0.1438 (7)	0.018*
C1	1.2275 (6)	0.3148 (4)	0.08300 (8)	0.0138 (8)
C2	1.4066 (6)	0.4158 (4)	0.09534 (8)	0.0175 (8)
H2A	1.4062	0.4477	0.1175	0.021*
C3	1.5882 (6)	0.4694 (4)	0.07423 (8)	0.0193 (9)
H3B	1.7151	0.5378	0.0822	0.023*
C4	1.5863 (7)	0.4244 (4)	0.04181 (9)	0.0237 (9)
H4A	1.7092	0.4635	0.0275	0.028*
C5	1.4054 (6)	0.3227 (4)	0.03045 (8)	0.0239 (9)
H5A	1.4044	0.2909	0.0082	0.029*
C6	1.2250 (6)	0.2665 (4)	0.05106 (7)	0.0186 (8)
H6A	1.1010	0.1954	0.0432	0.022*
C7	0.8931 (6)	0.4166 (4)	0.18657 (8)	0.0147 (8)
C8	1.0704 (7)	0.5046 (4)	0.20239 (8)	0.0232 (9)
H8A	1.2141	0.5378	0.1913	0.028*
C9	1.0358 (7)	0.5446 (4)	0.23511 (8)	0.0270 (9)
H9A	1.1575	0.6045	0.2465	0.032*
C10	0.8268 (7)	0.4975 (4)	0.25076 (9)	0.0277 (10)
H10A	0.8030	0.5250	0.2730	0.033*
C11	0.6510 (7)	0.4101 (4)	0.23415 (8)	0.0220 (9)
H11A	0.5062	0.3777	0.2451	0.026*
C12	0.6827 (6)	0.3689 (4)	0.20180 (8)	0.0170 (8)
H12A	0.5611	0.3090	0.1904	0.020*
C13	0.6168 (7)	−0.1630 (4)	0.18811 (7)	0.0273 (10)
H13A	0.4918	−0.2374	0.1966	0.041*
H13B	0.5715	−0.0493	0.1930	0.041*
H13C	0.7740	−0.1882	0.1983	0.041*
C14	0.6370 (6)	−0.1851 (4)	0.15156 (7)	0.0213 (9)
H14A	0.4814	−0.1515	0.1413	0.026*
H14B	0.6628	−0.3028	0.1467	0.026*
C15	0.8451 (6)	−0.0856 (4)	0.13654 (7)	0.0130 (7)
H15A	1.0005	−0.1226	0.1469	0.016*
C16	0.8667 (6)	−0.1162 (4)	0.10011 (8)	0.0131 (8)
C17	1.0577 (6)	−0.2086 (4)	0.08788 (7)	0.0175 (8)
H17A	1.1767	−0.2512	0.1024	0.021*
C18	1.0790 (6)	−0.2405 (4)	0.05478 (8)	0.0211 (9)
H18A	1.2099	−0.3055	0.0468	0.025*
C19	0.9076 (6)	−0.1766 (4)	0.03360 (8)	0.0213 (9)
H19A	0.9221	−0.1965	0.0109	0.026*
C20	0.7162 (7)	−0.0845 (4)	0.04518 (8)	0.0211 (9)
H20A	0.5981	−0.0413	0.0306	0.025*
C21	0.6966 (6)	−0.0549 (4)	0.07836 (8)	0.0178 (9)
H21A	0.5640	0.0086	0.0863	0.021*

	U11	U22	U33	U12	U13	U23
P1	0.0134 (4)	0.0160 (4)	0.0139 (5)	−0.0003 (4)	−0.0006 (4)	−0.0004 (4)
O1	0.0146 (12)	0.0300 (15)	0.0122 (11)	−0.0012 (13)	0.0002 (10)	0.0020 (10)
O2	0.0200 (13)	0.0115 (12)	0.0163 (12)	0.0000 (11)	−0.0005 (11)	−0.0006 (10)
O3	0.0136 (12)	0.0178 (13)	0.0191 (13)	−0.0002 (11)	−0.0008 (10)	−0.0001 (11)
N1	0.0132 (14)	0.0114 (15)	0.0119 (16)	0.0030 (13)	−0.0001 (14)	−0.0015 (13)
C1	0.0098 (18)	0.013 (2)	0.018 (2)	0.0016 (16)	0.0051 (14)	0.0038 (16)
C2	0.0175 (19)	0.0173 (18)	0.018 (2)	0.0038 (17)	0.0013 (16)	−0.0023 (16)
C3	0.0152 (19)	0.0126 (19)	0.030 (2)	−0.0028 (17)	−0.0017 (17)	0.0017 (17)
C4	0.020 (2)	0.022 (2)	0.029 (2)	0.0019 (18)	0.0120 (18)	0.0046 (19)
C5	0.028 (2)	0.031 (2)	0.0119 (19)	0.0009 (19)	0.0064 (16)	−0.0006 (17)
C6	0.0222 (19)	0.018 (2)	0.0157 (19)	−0.0053 (18)	−0.0017 (16)	0.0002 (16)
C7	0.0164 (19)	0.0115 (18)	0.0162 (19)	0.0029 (17)	−0.0031 (16)	−0.0003 (16)
C8	0.019 (2)	0.0183 (19)	0.032 (2)	−0.0011 (19)	0.0001 (19)	−0.0022 (17)
C9	0.027 (2)	0.025 (2)	0.029 (2)	0.000 (2)	−0.009 (2)	−0.0110 (18)
C10	0.036 (3)	0.030 (2)	0.017 (2)	0.010 (2)	−0.007 (2)	−0.0079 (19)
C11	0.024 (2)	0.027 (2)	0.015 (2)	0.003 (2)	0.0002 (17)	0.0016 (18)
C12	0.0167 (19)	0.016 (2)	0.019 (2)	−0.0012 (17)	−0.0067 (16)	−0.0012 (16)
C13	0.037 (2)	0.025 (2)	0.020 (2)	−0.0053 (19)	0.0051 (18)	0.0021 (18)
C14	0.028 (2)	0.0157 (19)	0.020 (2)	−0.0020 (17)	−0.0016 (16)	−0.0034 (17)
C15	0.0115 (16)	0.0149 (18)	0.0128 (18)	0.0017 (15)	−0.0032 (16)	0.0010 (17)
C16	0.0141 (18)	0.0083 (18)	0.017 (2)	−0.0031 (16)	−0.0005 (15)	−0.0012 (15)
C17	0.0180 (18)	0.0196 (18)	0.0148 (18)	−0.0021 (19)	−0.0024 (15)	−0.0027 (17)
C18	0.019 (2)	0.019 (2)	0.025 (2)	−0.0018 (18)	0.0042 (16)	−0.0069 (17)
C19	0.033 (2)	0.021 (2)	0.0102 (18)	−0.0100 (18)	0.0022 (16)	−0.0018 (16)
C20	0.029 (2)	0.020 (2)	0.014 (2)	−0.0004 (19)	−0.0041 (18)	0.0012 (17)
C21	0.021 (2)	0.016 (2)	0.016 (2)	0.0027 (17)	−0.0030 (17)	−0.0042 (16)

P1—O3	1.465 (2)	C10—C11	1.380 (5)
P1—O1	1.582 (2)	C10—H10A	0.9500
P1—O2	1.586 (2)	C11—C12	1.384 (4)
P1—N1	1.613 (3)	C11—H11A	0.9500
O1—C1	1.400 (3)	C12—H12A	0.9500
O2—C7	1.417 (4)	C13—C14	1.519 (4)
N1—C15	1.469 (4)	C13—H13A	0.9800
N1—H1	0.838 (10)	C13—H13B	0.9800
C1—C6	1.372 (4)	C13—H13C	0.9800
C1—C2	1.378 (4)	C14—C15	1.530 (4)
C2—C3	1.392 (4)	C14—H14A	0.9900
C2—H2A	0.9500	C14—H14B	0.9900
C3—C4	1.384 (4)	C15—C16	1.525 (4)
C3—H3B	0.9500	C15—H15A	1.0000
C4—C5	1.374 (4)	C16—C17	1.385 (4)
C4—H4A	0.9500	C16—C21	1.386 (4)
C5—C6	1.382 (4)	C17—C18	1.392 (4)
C5—H5A	0.9500	C17—H17A	0.9500
C6—H6A	0.9500	C18—C19	1.384 (4)
C7—C12	1.370 (4)	C18—H18A	0.9500
C7—C8	1.373 (4)	C19—C20	1.376 (5)
C8—C9	1.398 (4)	C19—H19A	0.9500
C8—H8A	0.9500	C20—C21	1.391 (4)
C9—C10	1.370 (5)	C20—H20A	0.9500
C9—H9A	0.9500	C21—H21A	0.9500
O3—P1—O1	113.67 (13)	C10—C11—H11A	119.5
O3—P1—O2	116.68 (12)	C12—C11—H11A	119.5
O1—P1—O2	99.51 (12)	C7—C12—C11	118.5 (3)
O3—P1—N1	114.72 (13)	C7—C12—H12A	120.7
O1—P1—N1	105.78 (13)	C11—C12—H12A	120.7
O2—P1—N1	104.81 (13)	C14—C13—H13A	109.5
C1—O1—P1	128.3 (2)	C14—C13—H13B	109.5
C7—O2—P1	121.73 (19)	H13A—C13—H13B	109.5
C15—N1—P1	120.9 (2)	C14—C13—H13C	109.5
C15—N1—H1	113 (2)	H13A—C13—H13C	109.5
P1—N1—H1	121 (2)	H13B—C13—H13C	109.5
C6—C1—C2	122.1 (3)	C13—C14—C15	113.1 (3)
C6—C1—O1	115.6 (3)	C13—C14—H14A	109.0
C2—C1—O1	122.3 (3)	C15—C14—H14A	109.0
C1—C2—C3	117.9 (3)	C13—C14—H14B	109.0
C1—C2—H2A	121.1	C15—C14—H14B	109.0
C3—C2—H2A	121.1	H14A—C14—H14B	107.8
C4—C3—C2	120.9 (3)	N1—C15—C16	113.0 (3)
C4—C3—H3B	119.6	N1—C15—C14	109.0 (3)
C2—C3—H3B	119.6	C16—C15—C14	111.6 (3)
C5—C4—C3	119.6 (3)	N1—C15—H15A	107.7
C5—C4—H4A	120.2	C16—C15—H15A	107.7
C3—C4—H4A	120.2	C14—C15—H15A	107.7
C4—C5—C6	120.5 (3)	C17—C16—C21	118.0 (3)
C4—C5—H5A	119.7	C17—C16—C15	120.3 (3)
C6—C5—H5A	119.7	C21—C16—C15	121.6 (3)
C1—C6—C5	119.1 (3)	C16—C17—C18	121.4 (3)
C1—C6—H6A	120.5	C16—C17—H17A	119.3
C5—C6—H6A	120.5	C18—C17—H17A	119.3
C12—C7—C8	121.9 (3)	C19—C18—C17	119.3 (3)
C12—C7—O2	119.9 (3)	C19—C18—H18A	120.3
C8—C7—O2	118.0 (3)	C17—C18—H18A	120.3
C7—C8—C9	118.8 (4)	C20—C19—C18	120.4 (3)
C7—C8—H8A	120.6	C20—C19—H19A	119.8
C9—C8—H8A	120.6	C18—C19—H19A	119.8
C10—C9—C8	120.1 (4)	C19—C20—C21	119.6 (3)
C10—C9—H9A	120.0	C19—C20—H20A	120.2
C8—C9—H9A	120.0	C21—C20—H20A	120.2
C9—C10—C11	119.7 (3)	C16—C21—C20	121.3 (3)
C9—C10—H10A	120.1	C16—C21—H21A	119.3
C11—C10—H10A	120.1	C20—C21—H21A	119.3
C10—C11—C12	120.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.84 (1)	2.25 (1)	3.077 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.84 (1)	2.25 (1)	3.077 (3)	167 (3)

Symmetry code: (i) .