Diphenyl (methyl-amido)-phosphate.

The N-H bond in the title compound, C(13)H(14)NO(3)P, is syn-oriented relative to the P=O bond. The N atom deviates somewhat from planarity, the sum of the bond angles being 353.3°. The P atom has a distorted tetra-hedral coordination; its bond angles are in the range 93.96 (5)-116.83 (6)°. In the crystal, mol-ecules form centrosymmetric dimers through P=O⋯H-N hydrogen bonds.

Related literature

For general background, see: Pourayoubi et al. (2012 ▶). For bond lengths and angles in a related structure, see: Sabbaghi et al. (2011 ▶).

Experimental

Crystal data

C13H14NO3P

M = 263.22

Monoclinic,

a = 9.7652 (5) Å

b = 13.6368 (6) Å

c = 10.3537 (5) Å

β = 114.217 (6)°

V = 1257.43 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 120 K

0.50 × 0.50 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur (Sapphire2) diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.939, T max = 1.000

14649 measured reflections

2212 independent reflections

1871 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.09

2212 reflections

168 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (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: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681203869X/ld2070sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203869X/ld2070Isup2.hkl

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

C13H14NO3P	F(000) = 552
Mr = 263.22	Dx = 1.390 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.7652 (5) Å	Cell parameters from 7682 reflections
b = 13.6368 (6) Å	θ = 2.8–27.1°
c = 10.3537 (5) Å	µ = 0.22 mm−1
β = 114.217 (6)°	T = 120 K
V = 1257.43 (12) Å3	Block, white
Z = 4	0.50 × 0.50 × 0.40 mm

Oxford Diffraction Xcalibur (Sapphire2) diffractometer	2212 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1871 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 2.8°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −12→16
Tmin = 0.939, Tmax = 1.000	l = −12→12
14649 measured reflections

Refinement on F2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.046P)2 + 0.1667P] where P = (Fo2 + 2Fc2)/3
2212 reflections	(Δ/σ)max = 0.001
168 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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.

	x	y	z	Uiso*/Ueq
P1	0.51390 (4)	0.43348 (3)	0.30989 (4)	0.01769 (14)
O1	0.38345 (11)	0.43725 (7)	0.34520 (10)	0.0208 (3)
O2	0.50768 (12)	0.50885 (7)	0.18982 (10)	0.0223 (3)
O3	0.52841 (11)	0.34002 (7)	0.22495 (10)	0.0211 (3)
N1	0.67107 (14)	0.44375 (9)	0.44729 (14)	0.0207 (3)
H1N	0.662 (2)	0.4674 (13)	0.513 (2)	0.032 (5)*
C1	0.81454 (17)	0.45739 (12)	0.43646 (17)	0.0273 (4)
H1A	0.8961	0.4325	0.5225	0.041*
H1B	0.8303	0.5273	0.4256	0.041*
H1C	0.8133	0.4214	0.3540	0.041*
C2	0.47748 (15)	0.60922 (11)	0.19327 (15)	0.0188 (3)
C3	0.51171 (16)	0.66074 (11)	0.31815 (15)	0.0226 (3)
H3	0.5552	0.6285	0.4072	0.027*
C4	0.48104 (17)	0.76048 (12)	0.31004 (17)	0.0257 (4)
H4	0.5030	0.7967	0.3946	0.031*
C5	0.41887 (17)	0.80803 (12)	0.18051 (17)	0.0267 (4)
H5	0.3990	0.8764	0.1762	0.032*
C6	0.38592 (17)	0.75473 (12)	0.05730 (17)	0.0269 (4)
H6	0.3434	0.7869	−0.0318	0.032*
C7	0.41444 (16)	0.65494 (11)	0.06295 (15)	0.0228 (3)
H7	0.3910	0.6185	−0.0217	0.027*
C8	0.54261 (16)	0.24509 (11)	0.28322 (14)	0.0195 (3)
C9	0.68401 (17)	0.20402 (12)	0.34803 (16)	0.0249 (4)
H9	0.7707	0.2406	0.3583	0.030*
C10	0.69714 (18)	0.10862 (12)	0.39770 (16)	0.0272 (4)
H10	0.7936	0.0795	0.4431	0.033*
C11	0.57023 (18)	0.05567 (12)	0.38137 (16)	0.0264 (4)
H11	0.5797	−0.0099	0.4149	0.032*
C12	0.42946 (17)	0.09791 (12)	0.31628 (16)	0.0276 (4)
H12	0.3427	0.0613	0.3056	0.033*
C13	0.41468 (17)	0.19365 (12)	0.26646 (16)	0.0248 (4)
H13	0.3184	0.2231	0.2217	0.030*

	U11	U22	U33	U12	U13	U23
P1	0.0214 (2)	0.0152 (2)	0.0177 (2)	0.00056 (15)	0.00922 (16)	−0.00031 (15)
O1	0.0221 (5)	0.0185 (6)	0.0227 (5)	−0.0005 (4)	0.0100 (4)	−0.0020 (4)
O2	0.0332 (6)	0.0155 (6)	0.0210 (5)	0.0015 (4)	0.0141 (5)	0.0010 (4)
O3	0.0301 (6)	0.0149 (6)	0.0202 (5)	0.0020 (4)	0.0122 (4)	−0.0002 (4)
N1	0.0217 (7)	0.0224 (8)	0.0202 (7)	0.0009 (5)	0.0109 (6)	−0.0024 (6)
C1	0.0225 (8)	0.0297 (10)	0.0317 (9)	−0.0026 (7)	0.0130 (7)	−0.0037 (7)
C2	0.0188 (7)	0.0150 (8)	0.0248 (8)	−0.0001 (6)	0.0112 (6)	0.0010 (6)
C3	0.0255 (8)	0.0215 (9)	0.0203 (8)	−0.0002 (6)	0.0089 (6)	0.0012 (6)
C4	0.0296 (8)	0.0205 (9)	0.0288 (8)	−0.0019 (7)	0.0138 (7)	−0.0039 (7)
C5	0.0276 (8)	0.0169 (9)	0.0375 (9)	0.0032 (6)	0.0155 (7)	0.0031 (7)
C6	0.0260 (8)	0.0256 (9)	0.0275 (8)	0.0041 (7)	0.0095 (7)	0.0088 (7)
C7	0.0238 (8)	0.0244 (9)	0.0202 (8)	0.0000 (6)	0.0089 (6)	0.0004 (6)
C8	0.0278 (8)	0.0143 (8)	0.0184 (7)	0.0001 (6)	0.0116 (6)	−0.0021 (6)
C9	0.0241 (8)	0.0215 (9)	0.0306 (8)	−0.0022 (6)	0.0127 (7)	0.0000 (7)
C10	0.0273 (9)	0.0221 (9)	0.0318 (9)	0.0053 (7)	0.0117 (7)	0.0036 (7)
C11	0.0380 (9)	0.0184 (9)	0.0254 (8)	−0.0003 (7)	0.0156 (7)	0.0006 (7)
C12	0.0293 (9)	0.0259 (10)	0.0294 (9)	−0.0079 (7)	0.0138 (7)	−0.0029 (7)
C13	0.0220 (8)	0.0253 (10)	0.0255 (8)	0.0002 (7)	0.0083 (6)	−0.0019 (7)

P1—O1	1.4632 (10)	C5—C6	1.387 (2)
P1—O3	1.5875 (10)	C5—H5	0.9500
P1—O2	1.5949 (10)	C6—C7	1.385 (2)
P1—N1	1.6148 (13)	C6—H6	0.9500
O2—C2	1.4037 (18)	C7—H7	0.9500
O3—C8	1.4108 (17)	C8—C13	1.380 (2)
N1—C1	1.4625 (18)	C8—C9	1.382 (2)
N1—H1N	0.788 (18)	C9—C10	1.385 (2)
C1—H1A	0.9800	C9—H9	0.9500
C1—H1B	0.9800	C10—C11	1.383 (2)
C1—H1C	0.9800	C10—H10	0.9500
C2—C7	1.381 (2)	C11—C12	1.384 (2)
C2—C3	1.387 (2)	C11—H11	0.9500
C3—C4	1.388 (2)	C12—C13	1.389 (2)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.386 (2)	C13—H13	0.9500
C4—H4	0.9500
O1—P1—O3	116.83 (6)	C4—C5—H5	120.4
O1—P1—O2	114.42 (6)	C6—C5—H5	120.4
O3—P1—O2	93.96 (5)	C7—C6—C5	120.62 (14)
O1—P1—N1	112.78 (6)	C7—C6—H6	119.7
O3—P1—N1	106.80 (6)	C5—C6—H6	119.7
O2—P1—N1	110.45 (6)	C2—C7—C6	119.08 (14)
C2—O2—P1	123.35 (9)	C2—C7—H7	120.5
C8—O3—P1	121.01 (9)	C6—C7—H7	120.5
C1—N1—P1	122.53 (10)	C13—C8—C9	121.84 (14)
C1—N1—H1N	117.4 (13)	C13—C8—O3	119.17 (13)
P1—N1—H1N	113.4 (14)	C9—C8—O3	118.87 (13)
N1—C1—H1A	109.5	C8—C9—C10	118.86 (14)
N1—C1—H1B	109.5	C8—C9—H9	120.6
H1A—C1—H1B	109.5	C10—C9—H9	120.6
N1—C1—H1C	109.5	C11—C10—C9	120.19 (15)
H1A—C1—H1C	109.5	C11—C10—H10	119.9
H1B—C1—H1C	109.5	C9—C10—H10	119.9
C7—C2—C3	121.52 (14)	C10—C11—C12	120.21 (15)
C7—C2—O2	115.43 (13)	C10—C11—H11	119.9
C3—C2—O2	123.03 (13)	C12—C11—H11	119.9
C2—C3—C4	118.46 (14)	C11—C12—C13	120.20 (15)
C2—C3—H3	120.8	C11—C12—H12	119.9
C4—C3—H3	120.8	C13—C12—H12	119.9
C5—C4—C3	121.02 (15)	C8—C13—C12	118.69 (14)
C5—C4—H4	119.5	C8—C13—H13	120.7
C3—C4—H4	119.5	C12—C13—H13	120.7
C4—C5—C6	119.30 (15)
O1—P1—O2—C2	50.74 (12)	C4—C5—C6—C7	0.1 (2)
O3—P1—O2—C2	172.62 (10)	C3—C2—C7—C6	0.5 (2)
N1—P1—O2—C2	−77.81 (11)	O2—C2—C7—C6	−177.80 (12)
O1—P1—O3—C8	−61.57 (11)	C5—C6—C7—C2	−0.6 (2)
O2—P1—O3—C8	178.47 (10)	P1—O3—C8—C13	85.76 (15)
N1—P1—O3—C8	65.73 (11)	P1—O3—C8—C9	−98.12 (14)
O1—P1—N1—C1	−170.21 (11)	C13—C8—C9—C10	−0.2 (2)
O3—P1—N1—C1	60.14 (13)	O3—C8—C9—C10	−176.17 (13)
O2—P1—N1—C1	−40.78 (14)	C8—C9—C10—C11	0.5 (2)
P1—O2—C2—C7	−153.60 (11)	C9—C10—C11—C12	−0.5 (2)
P1—O2—C2—C3	28.15 (18)	C10—C11—C12—C13	0.2 (2)
C7—C2—C3—C4	0.1 (2)	C9—C8—C13—C12	−0.1 (2)
O2—C2—C3—C4	178.21 (13)	O3—C8—C13—C12	175.92 (13)
C2—C3—C4—C5	−0.6 (2)	C11—C12—C13—C8	0.0 (2)
C3—C4—C5—C6	0.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.788 (18)	2.141 (18)	2.9106 (17)	165.1 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.788 (18)	2.141 (18)	2.9106 (17)	165.1 (18)

Symmetry code: (i) .