Diphenyl (benzyl-amido)phosphate.

The title compound, C(19)H(18)NO(3)P, was prepared by the reaction of diphenyl phospho-rochloridate and benzyl-amine. In the crystal structure, mol-ecules are linked via N-H⋯O=P hydrogen bonds into extended chains parallel to the c axis.

Related literature

For related structures, see: Bao & Wulff (1993 ▶); Gholivand et al. (2005 ▶); Karolak-Wojciechowska et al. (1979 ▶).

Experimental

Crystal data

C19H18NO3P

M = 339.31

Monoclinic,

a = 10.0226 (5) Å

b = 19.2450 (8) Å

c = 10.2273 (5) Å

β = 115.375 (6)°

V = 1782.38 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.17 mm−1

T = 295 K

0.43 × 0.28 × 0.17 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector

Absorption correction: multi-scan CrysAlis PRO (Oxford Diffraction, 2009 ▶) T min = 0.977, T max = 1.000

8248 measured reflections

4105 independent reflections

2568 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.102

S = 0.91

4105 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053744/lh2963sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053744/lh2963Isup2.hkl

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

C19H18NO3P	F(000) = 712
Mr = 339.31	Dx = 1.264 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3418 reflections
a = 10.0226 (5) Å	θ = 3.2–29.1°
b = 19.2450 (8) Å	µ = 0.17 mm−1
c = 10.2273 (5) Å	T = 295 K
β = 115.375 (6)°	Prism, colorless
V = 1782.38 (17) Å3	0.43 × 0.28 × 0.17 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer with a Sapphire3 (Gemini Mo) detector	4105 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2568 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 16.3280 pixels mm-1	θmax = 29.2°, θmin = 3.2°
ω scans	h = −7→13
Absorption correction: multi-scan CrysAlis (Oxford Diffraction, 2009)	k = −17→24
Tmin = 0.977, Tmax = 1.000	l = −13→13
8248 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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max < 0.001
4105 reflections	Δρmax = 0.19 e Å−3
218 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (10)

Experimental. #__ type_ start__ end____ width___ exp.time_ 1 omega -51.00 47.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 - 37.0000 300.0000 98#__ type_ start__ end____ width___ exp.time_ 2 omega 5.00 91.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 77.0000 150.0000 86#__ type_ start__ end____ width___ exp.time_ 3 omega -6.00 41.00 1.0000 19.0400 omega____ theta____ kappa____ phi______ frames - 21.0423 - 77.0000 240.0000 47

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
P	0.97981 (4)	0.22655 (2)	0.06013 (4)	0.04171 (14)
O1	0.87224 (12)	0.16886 (6)	−0.04116 (11)	0.0509 (3)
O2	1.13289 (12)	0.18955 (6)	0.09457 (11)	0.0514 (3)
O3	0.95622 (13)	0.24405 (6)	0.18721 (10)	0.0563 (3)
N	0.97260 (16)	0.29192 (7)	−0.03860 (13)	0.0491 (4)
H	0.9660	0.2836	−0.1238	0.059*
C17	1.2659 (3)	0.00509 (17)	0.3197 (5)	0.1137 (12)
H17	1.2997	−0.0363	0.3701	0.136*
C2	0.84557 (18)	0.40475 (9)	−0.10133 (16)	0.0458 (4)
C1	0.97616 (19)	0.36437 (9)	0.00303 (17)	0.0507 (4)
H1A	1.0661	0.3856	0.0084	0.061*
H1B	0.9782	0.3667	0.0986	0.061*
C8	0.71826 (18)	0.17787 (9)	−0.09973 (17)	0.0490 (4)
C14	1.17229 (17)	0.12655 (9)	0.17145 (18)	0.0495 (4)
C13	0.6460 (2)	0.20013 (13)	−0.2392 (2)	0.0841 (7)
H13	0.6973	0.2108	−0.2939	0.101*
C3	0.7036 (2)	0.38616 (11)	−0.1264 (2)	0.0617 (5)
H3	0.6885	0.3474	−0.0802	0.074*
C7	0.8641 (2)	0.46219 (10)	−0.17277 (18)	0.0576 (5)
H7	0.9585	0.4753	−0.1589	0.069*
C9	0.6453 (2)	0.16092 (11)	−0.0180 (2)	0.0638 (5)
H9	0.6972	0.1456	0.0768	0.077*
C15	1.2344 (2)	0.12743 (12)	0.3197 (2)	0.0668 (5)
H15	1.2451	0.1690	0.3697	0.080*
C5	0.6047 (2)	0.48142 (13)	−0.2871 (2)	0.0779 (6)
H5	0.5239	0.5074	−0.3487	0.094*
C19	1.1552 (2)	0.06622 (12)	0.0974 (2)	0.0756 (6)
H19	1.1122	0.0662	−0.0032	0.091*
C6	0.7436 (2)	0.50035 (11)	−0.2647 (2)	0.0735 (6)
H6	0.7576	0.5392	−0.3116	0.088*
C10	0.4937 (2)	0.16685 (13)	−0.0781 (3)	0.0870 (7)
H10	0.4423	0.1553	−0.0240	0.104*
C18	1.2022 (3)	0.00495 (13)	0.1733 (5)	0.1065 (10)
H18	1.1901	−0.0367	0.1234	0.128*
C4	0.5843 (2)	0.42419 (14)	−0.2187 (2)	0.0765 (6)
H4	0.4893	0.4109	−0.2347	0.092*
C16	1.2806 (3)	0.06559 (18)	0.3931 (3)	0.0959 (9)
H16	1.3221	0.0652	0.4937	0.115*
C11	0.4196 (3)	0.18955 (14)	−0.2160 (4)	0.1061 (10)
H11	0.3173	0.1937	−0.2562	0.127*
C12	0.4943 (3)	0.20642 (15)	−0.2968 (3)	0.1170 (11)
H12	0.4423	0.2222	−0.3912	0.140*

	U11	U22	U33	U12	U13	U23
P	0.0509 (2)	0.0414 (3)	0.0336 (2)	0.0017 (2)	0.01886 (17)	0.0016 (2)
O1	0.0523 (7)	0.0403 (7)	0.0545 (6)	0.0012 (5)	0.0175 (5)	−0.0030 (5)
O2	0.0500 (6)	0.0496 (8)	0.0554 (6)	0.0035 (6)	0.0234 (5)	0.0076 (6)
O3	0.0751 (8)	0.0621 (9)	0.0367 (6)	0.0050 (7)	0.0287 (5)	0.0045 (6)
N	0.0775 (9)	0.0403 (9)	0.0341 (6)	0.0033 (7)	0.0283 (6)	−0.0005 (6)
C17	0.0716 (17)	0.080 (2)	0.198 (4)	0.0297 (16)	0.067 (2)	0.068 (3)
C2	0.0540 (9)	0.0409 (10)	0.0455 (8)	−0.0013 (8)	0.0242 (7)	−0.0057 (8)
C1	0.0614 (10)	0.0417 (11)	0.0466 (9)	−0.0041 (9)	0.0210 (8)	−0.0025 (8)
C8	0.0525 (10)	0.0325 (10)	0.0494 (9)	−0.0007 (8)	0.0097 (8)	−0.0013 (8)
C14	0.0388 (8)	0.0452 (11)	0.0628 (11)	0.0030 (8)	0.0202 (8)	0.0040 (9)
C13	0.0884 (16)	0.0824 (17)	0.0522 (11)	−0.0214 (13)	0.0022 (10)	0.0109 (11)
C3	0.0655 (12)	0.0597 (13)	0.0704 (11)	−0.0050 (10)	0.0390 (10)	0.0001 (10)
C7	0.0605 (11)	0.0512 (12)	0.0630 (11)	−0.0032 (10)	0.0282 (9)	0.0037 (10)
C9	0.0561 (11)	0.0623 (14)	0.0643 (10)	−0.0019 (10)	0.0177 (9)	−0.0007 (10)
C15	0.0664 (11)	0.0729 (15)	0.0637 (11)	0.0193 (11)	0.0305 (9)	0.0141 (11)
C5	0.0683 (14)	0.0810 (18)	0.0751 (14)	0.0245 (13)	0.0216 (11)	0.0064 (13)
C19	0.0555 (11)	0.0584 (15)	0.0963 (15)	0.0033 (11)	0.0167 (10)	−0.0175 (13)
C6	0.0884 (16)	0.0574 (14)	0.0726 (13)	0.0109 (12)	0.0325 (12)	0.0164 (11)
C10	0.0579 (13)	0.0773 (18)	0.1166 (18)	−0.0056 (12)	0.0286 (13)	−0.0169 (15)
C18	0.0680 (15)	0.0452 (16)	0.190 (3)	0.0061 (13)	0.0401 (19)	−0.005 (2)
C4	0.0524 (11)	0.0902 (18)	0.0894 (14)	0.0068 (12)	0.0326 (11)	−0.0006 (14)
C16	0.0857 (16)	0.116 (2)	0.0997 (17)	0.0436 (17)	0.0529 (14)	0.0563 (19)
C11	0.0530 (13)	0.0567 (16)	0.153 (3)	−0.0022 (12)	−0.0092 (16)	0.0056 (17)
C12	0.093 (2)	0.090 (2)	0.0937 (18)	−0.0231 (16)	−0.0313 (15)	0.0330 (15)

P—O3	1.4567 (10)	C3—C4	1.375 (3)
P—O1	1.5844 (12)	C3—H3	0.9300
P—O2	1.5880 (12)	C7—C6	1.381 (3)
P—N	1.5952 (14)	C7—H7	0.9300
O1—C8	1.4065 (19)	C9—C10	1.379 (3)
O2—C14	1.406 (2)	C9—H9	0.9300
N—C1	1.454 (2)	C15—C16	1.377 (3)
N—H	0.8600	C15—H15	0.9300
C17—C18	1.353 (4)	C5—C6	1.360 (3)
C17—C16	1.359 (4)	C5—C4	1.366 (3)
C17—H17	0.9300	C5—H5	0.9300
C2—C3	1.381 (2)	C19—C18	1.379 (4)
C2—C7	1.381 (2)	C19—H19	0.9300
C2—C1	1.503 (2)	C6—H6	0.9300
C1—H1A	0.9700	C10—C11	1.355 (4)
C1—H1B	0.9700	C10—H10	0.9300
C8—C13	1.363 (2)	C18—H18	0.9300
C8—C9	1.365 (3)	C4—H4	0.9300
C14—C19	1.356 (3)	C16—H16	0.9300
C14—C15	1.370 (2)	C11—C12	1.370 (4)
C13—C12	1.381 (3)	C11—H11	0.9300
C13—H13	0.9300	C12—H12	0.9300
O3—P—O1	114.84 (7)	C2—C7—H7	119.7
O3—P—O2	114.62 (6)	C6—C7—H7	119.7
O1—P—O2	98.80 (6)	C8—C9—C10	119.0 (2)
O3—P—N	113.69 (7)	C8—C9—H9	120.5
O1—P—N	107.77 (6)	C10—C9—H9	120.5
O2—P—N	105.75 (7)	C14—C15—C16	118.7 (2)
C8—O1—P	120.47 (10)	C14—C15—H15	120.7
C14—O2—P	121.58 (10)	C16—C15—H15	120.7
C1—N—P	125.61 (10)	C6—C5—C4	119.8 (2)
C1—N—H	117.2	C6—C5—H5	120.1
P—N—H	117.2	C4—C5—H5	120.1
C18—C17—C16	120.1 (3)	C14—C19—C18	119.2 (2)
C18—C17—H17	120.0	C14—C19—H19	120.4
C16—C17—H17	120.0	C18—C19—H19	120.4
C3—C2—C7	118.08 (17)	C5—C6—C7	120.3 (2)
C3—C2—C1	120.83 (16)	C5—C6—H6	119.8
C7—C2—C1	121.08 (16)	C7—C6—H6	119.8
N—C1—C2	112.54 (13)	C11—C10—C9	119.9 (2)
N—C1—H1A	109.1	C11—C10—H10	120.1
C2—C1—H1A	109.1	C9—C10—H10	120.1
N—C1—H1B	109.1	C17—C18—C19	120.4 (3)
C2—C1—H1B	109.1	C17—C18—H18	119.8
H1A—C1—H1B	107.8	C19—C18—H18	119.8
C13—C8—C9	122.16 (18)	C5—C4—C3	120.2 (2)
C13—C8—O1	118.58 (17)	C5—C4—H4	119.9
C9—C8—O1	119.17 (15)	C3—C4—H4	119.9
C19—C14—C15	121.14 (19)	C17—C16—C15	120.5 (3)
C19—C14—O2	119.20 (16)	C17—C16—H16	119.7
C15—C14—O2	119.57 (17)	C15—C16—H16	119.7
C8—C13—C12	117.9 (2)	C10—C11—C12	120.5 (2)
C8—C13—H13	121.0	C10—C11—H11	119.8
C12—C13—H13	121.0	C12—C11—H11	119.8
C4—C3—C2	120.91 (19)	C11—C12—C13	120.5 (2)
C4—C3—H3	119.5	C11—C12—H12	119.7
C2—C3—H3	119.5	C13—C12—H12	119.7
C2—C7—C6	120.63 (18)
O3—P—O1—C8	56.68 (13)	C3—C2—C7—C6	1.0 (3)
O2—P—O1—C8	179.11 (11)	C1—C2—C7—C6	−177.78 (16)
N—P—O1—C8	−71.14 (13)	C13—C8—C9—C10	−0.4 (3)
O3—P—O2—C14	58.59 (14)	O1—C8—C9—C10	−177.10 (18)
O1—P—O2—C14	−63.99 (12)	C19—C14—C15—C16	0.5 (3)
N—P—O2—C14	−175.37 (11)	O2—C14—C15—C16	−176.02 (16)
O3—P—N—C1	13.52 (17)	C15—C14—C19—C18	−0.5 (3)
O1—P—N—C1	142.00 (14)	O2—C14—C19—C18	176.05 (17)
O2—P—N—C1	−113.09 (14)	C4—C5—C6—C7	−0.3 (3)
P—N—C1—C2	−124.33 (14)	C2—C7—C6—C5	−0.6 (3)
C3—C2—C1—N	60.3 (2)	C8—C9—C10—C11	−0.3 (4)
C7—C2—C1—N	−120.96 (17)	C16—C17—C18—C19	1.7 (4)
P—O1—C8—C13	99.80 (18)	C14—C19—C18—C17	−0.6 (3)
P—O1—C8—C9	−83.34 (19)	C6—C5—C4—C3	0.7 (3)
P—O2—C14—C19	99.71 (17)	C2—C3—C4—C5	−0.2 (3)
P—O2—C14—C15	−83.73 (17)	C18—C17—C16—C15	−1.7 (4)
C9—C8—C13—C12	1.0 (3)	C14—C15—C16—C17	0.6 (3)
O1—C8—C13—C12	177.8 (2)	C9—C10—C11—C12	0.3 (4)
C7—C2—C3—C4	−0.7 (3)	C10—C11—C12—C13	0.4 (4)
C1—C2—C3—C4	178.17 (17)	C8—C13—C12—C11	−1.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O3i	0.86	1.97	2.8241 (15)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯O3i	0.86	1.97	2.8241 (15)	175

Symmetry code: (i) .