Diisopropyl [(benzoyl-amino)-(phen-yl)meth-yl]phospho-nate.

The title compound, C(20)H(26)NO(4)P, has been obtained by the reaction of benzoyl chloride and diisoprop-yl[amino-(phen-yl)meth-yl]phospho-nate. The dihedral angle between the planes of the benzoyl-amino group and the phenyl ring is 77.0 (2)°. The crystal structure is stabilized by strong inter-molecular N-H⋯O hydrogen bonds between the doubly bonded phosphoryl O atom and the amide N atom which link the mol-ecules into pairs about a center of symmetry.

Related literature

For the biological activity and pharmaceutical inter­est of α-hydroxy­phospho­nic acid esters, see: Stowasser et al. (1992 ▶); Chen et al. (1995 ▶). For their use as reagents in the synthesis of enol ethers and α-ketophospho­nates, see: Babak & Rahman (2001 ▶). For the synthesis, see: Drescher et al. (1995 ▶). For bond lengths and angles in related compunds, see: Smaardijk et al. (1985 ▶).

Experimental

Crystal data

C20H26NO4P

M = 375.39

Triclinic,

a = 10.839 (4) Å

b = 10.925 (5) Å

c = 11.057 (5) Å

α = 61.364 (8)°

β = 83.362 (8)°

γ = 60.470 (6)°

V = 987.3 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.16 mm−1

T = 273 K

0.28 × 0.21 × 0.05 mm

Data collection

Bruker SMART APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.956, T max = 0.992

4991 measured reflections

3411 independent reflections

2509 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.174

S = 0.98

3411 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.44 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006382/fl2235sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006382/fl2235Isup2.hkl

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

C20H26NO4P	Z = 2
Mr = 375.39	F(000) = 400
Triclinic, P1	Dx = 1.263 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.839 (4) Å	Cell parameters from 1689 reflections
b = 10.925 (5) Å	θ = 2.3–27.7°
c = 11.057 (5) Å	µ = 0.16 mm−1
α = 61.364 (8)°	T = 273 K
β = 83.362 (8)°	Chunk, colorless
γ = 60.470 (6)°	0.28 × 0.21 × 0.05 mm
V = 987.3 (7) Å3

Bruker APEX area-detector diffractometer	3411 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.956, Tmax = 0.992	k = −12→12
4991 measured reflections	l = −10→13

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.174	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.097P)2] where P = (Fo2 + 2Fc2)/3
3411 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.44 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	0.73254 (8)	0.85680 (9)	0.47527 (8)	0.0311 (3)
N1	0.6453 (2)	0.6827 (3)	0.6988 (3)	0.0310 (6)
H1A	0.5566	0.7577	0.6718	0.037*
O1	0.8049 (2)	0.4184 (2)	0.8105 (3)	0.0546 (7)
C1	0.6797 (3)	0.5282 (4)	0.7762 (3)	0.0339 (7)
O2	0.6331 (2)	1.0278 (2)	0.4252 (2)	0.0412 (6)
C2	0.5598 (3)	0.4933 (3)	0.8226 (3)	0.0336 (7)
O3	0.6811 (2)	0.7980 (2)	0.3986 (2)	0.0400 (6)
C3	0.5965 (4)	0.3371 (4)	0.9147 (4)	0.0505 (9)
H3A	0.6928	0.2572	0.9424	0.061*
O4	0.8922 (2)	0.8119 (2)	0.4564 (2)	0.0401 (6)
C4	0.4921 (4)	0.2969 (5)	0.9671 (4)	0.0602 (11)
H4A	0.5182	0.1906	1.0313	0.072*
C5	0.3507 (4)	0.4130 (5)	0.9247 (4)	0.0514 (9)
H5A	0.2804	0.3859	0.9603	0.062*
C6	0.3123 (4)	0.5681 (4)	0.8304 (4)	0.0549 (10)
H6A	0.2158	0.6472	0.8006	0.066*
C7	0.4171 (3)	0.6079 (4)	0.7792 (4)	0.0505 (9)
H7A	0.3905	0.7142	0.7142	0.061*
C8	0.7582 (3)	0.7231 (3)	0.6607 (3)	0.0305 (7)
H8A	0.8470	0.6220	0.6812	0.037*
C9	0.7819 (3)	0.7826 (3)	0.7489 (3)	0.0307 (7)
C10	0.6722 (3)	0.9170 (4)	0.7536 (3)	0.0431 (8)
H10A	0.5844	0.9768	0.6961	0.052*
C11	0.6917 (4)	0.9627 (4)	0.8423 (4)	0.0531 (9)
H11A	0.6166	1.0523	0.8456	0.064*
C12	0.8210 (4)	0.8774 (5)	0.9261 (4)	0.0562 (10)
H12A	0.8336	0.9095	0.9856	0.067*
C13	0.9309 (4)	0.7456 (5)	0.9221 (4)	0.0526 (9)
H13A	1.0191	0.6879	0.9784	0.063*
C14	0.9111 (3)	0.6979 (4)	0.8344 (3)	0.0398 (8)
H14A	0.9862	0.6070	0.8329	0.048*
C15	0.7424 (4)	0.6316 (4)	0.4291 (4)	0.0435 (8)
H15A	0.7990	0.5581	0.5230	0.052*
C16	0.6184 (4)	0.6079 (5)	0.4248 (4)	0.0608 (10)
H16A	0.5615	0.6255	0.4942	0.091*
H16B	0.6538	0.5000	0.4432	0.091*
H16C	0.5604	0.6832	0.3342	0.091*
C17	0.8383 (4)	0.6056 (5)	0.3243 (4)	0.0635 (11)
H17A	0.9161	0.6209	0.3328	0.095*
H17B	0.7841	0.6815	0.2319	0.095*
H17C	0.8758	0.4979	0.3409	0.095*
C18	0.9332 (4)	0.9289 (4)	0.3580 (4)	0.0458 (8)
H18A	0.8731	1.0307	0.3593	0.055*
C19	0.9101 (5)	0.9581 (6)	0.2149 (4)	0.0810 (14)
H19A	0.8101	1.0015	0.1875	0.121*
H19B	0.9658	0.8583	0.2131	0.121*
H19C	0.9393	1.0334	0.1513	0.121*
C20	1.0845 (4)	0.8639 (6)	0.4093 (5)	0.0816 (14)
H20A	1.0916	0.8510	0.5009	0.122*
H20B	1.1162	0.9373	0.3470	0.122*
H20C	1.1438	0.7612	0.4133	0.122*

	U11	U22	U33	U12	U13	U23
P1	0.0254 (4)	0.0278 (5)	0.0360 (5)	−0.0115 (3)	0.0062 (3)	−0.0149 (4)
N1	0.0210 (12)	0.0262 (13)	0.0398 (14)	−0.0105 (10)	0.0066 (11)	−0.0139 (12)
O1	0.0308 (12)	0.0297 (13)	0.0752 (18)	−0.0100 (10)	0.0017 (12)	−0.0102 (13)
C1	0.0348 (17)	0.0299 (17)	0.0363 (17)	−0.0170 (14)	0.0064 (14)	−0.0150 (15)
O2	0.0342 (11)	0.0288 (12)	0.0497 (13)	−0.0118 (9)	0.0050 (10)	−0.0155 (11)
C2	0.0407 (17)	0.0328 (17)	0.0343 (17)	−0.0228 (15)	0.0099 (14)	−0.0176 (15)
O3	0.0379 (12)	0.0357 (12)	0.0442 (12)	−0.0141 (10)	0.0030 (10)	−0.0217 (11)
C3	0.049 (2)	0.036 (2)	0.054 (2)	−0.0231 (17)	0.0061 (18)	−0.0111 (18)
O4	0.0284 (11)	0.0367 (12)	0.0448 (13)	−0.0162 (10)	0.0120 (10)	−0.0142 (11)
C4	0.075 (3)	0.050 (2)	0.055 (2)	−0.046 (2)	0.011 (2)	−0.011 (2)
C5	0.059 (2)	0.073 (3)	0.052 (2)	−0.051 (2)	0.0245 (19)	−0.035 (2)
C6	0.0391 (19)	0.055 (2)	0.077 (3)	−0.0298 (18)	0.0200 (19)	−0.032 (2)
C7	0.0383 (18)	0.0377 (19)	0.070 (2)	−0.0226 (16)	0.0128 (18)	−0.0197 (19)
C8	0.0236 (14)	0.0258 (16)	0.0400 (17)	−0.0107 (12)	0.0052 (13)	−0.0164 (15)
C9	0.0266 (15)	0.0321 (17)	0.0336 (16)	−0.0164 (13)	0.0097 (13)	−0.0155 (15)
C10	0.0386 (18)	0.0392 (19)	0.0472 (19)	−0.0152 (15)	0.0013 (16)	−0.0216 (17)
C11	0.057 (2)	0.050 (2)	0.059 (2)	−0.0245 (19)	0.012 (2)	−0.035 (2)
C12	0.080 (3)	0.068 (3)	0.052 (2)	−0.053 (2)	0.019 (2)	−0.036 (2)
C13	0.052 (2)	0.066 (2)	0.044 (2)	−0.040 (2)	0.0010 (18)	−0.018 (2)
C14	0.0338 (17)	0.0424 (19)	0.0400 (17)	−0.0211 (15)	0.0077 (15)	−0.0163 (16)
C15	0.0454 (19)	0.0363 (18)	0.048 (2)	−0.0177 (15)	0.0026 (17)	−0.0213 (17)
C16	0.064 (2)	0.068 (3)	0.072 (3)	−0.041 (2)	0.019 (2)	−0.043 (2)
C17	0.058 (2)	0.068 (3)	0.082 (3)	−0.033 (2)	0.033 (2)	−0.052 (3)
C18	0.0456 (19)	0.044 (2)	0.049 (2)	−0.0285 (17)	0.0128 (17)	−0.0182 (18)
C19	0.095 (3)	0.108 (4)	0.050 (2)	−0.073 (3)	0.020 (2)	−0.023 (3)
C20	0.063 (3)	0.094 (3)	0.074 (3)	−0.056 (3)	0.006 (2)	−0.013 (3)

P1—O2	1.456 (2)	C10—H10A	0.9300
P1—O3	1.559 (2)	C11—C12	1.369 (5)
P1—O4	1.567 (2)	C11—H11A	0.9300
P1—C8	1.809 (3)	C12—C13	1.361 (5)
N1—C1	1.337 (4)	C12—H12A	0.9300
N1—C8	1.451 (4)	C13—C14	1.379 (5)
N1—H1A	0.8600	C13—H13A	0.9300
O1—C1	1.226 (3)	C14—H14A	0.9300
C1—C2	1.498 (4)	C15—C16	1.498 (5)
C2—C3	1.365 (4)	C15—C17	1.500 (5)
C2—C7	1.370 (4)	C15—H15A	0.9800
O3—C15	1.460 (4)	C16—H16A	0.9600
C3—C4	1.380 (5)	C16—H16B	0.9600
C3—H3A	0.9300	C16—H16C	0.9600
O4—C18	1.460 (4)	C17—H17A	0.9600
C4—C5	1.363 (5)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.358 (5)	C18—C20	1.482 (5)
C5—H5A	0.9300	C18—C19	1.483 (5)
C6—C7	1.380 (5)	C18—H18A	0.9800
C6—H6A	0.9300	C19—H19A	0.9600
C7—H7A	0.9300	C19—H19B	0.9600
C8—C9	1.507 (4)	C19—H19C	0.9600
C8—H8A	0.9800	C20—H20A	0.9600
C9—C14	1.378 (4)	C20—H20B	0.9600
C9—C10	1.382 (4)	C20—H20C	0.9600
C10—C11	1.370 (4)
O2—P1—O3	109.31 (12)	C10—C11—H11A	119.7
O2—P1—O4	114.66 (12)	C13—C12—C11	119.9 (3)
O3—P1—O4	108.59 (12)	C13—C12—H12A	120.0
O2—P1—C8	116.66 (13)	C11—C12—H12A	120.0
O3—P1—C8	107.29 (13)	C12—C13—C14	119.7 (3)
O4—P1—C8	99.67 (12)	C12—C13—H13A	120.1
C1—N1—C8	119.7 (2)	C14—C13—H13A	120.1
C1—N1—H1A	120.1	C9—C14—C13	121.2 (3)
C8—N1—H1A	120.1	C9—C14—H14A	119.4
O1—C1—N1	121.6 (3)	C13—C14—H14A	119.4
O1—C1—C2	120.7 (3)	O3—C15—C16	106.6 (3)
N1—C1—C2	117.7 (3)	O3—C15—C17	108.8 (3)
C3—C2—C7	118.6 (3)	C16—C15—C17	113.3 (3)
C3—C2—C1	117.3 (3)	O3—C15—H15A	109.4
C7—C2—C1	124.1 (3)	C16—C15—H15A	109.4
C15—O3—P1	126.33 (19)	C17—C15—H15A	109.4
C2—C3—C4	120.6 (3)	C15—C16—H16A	109.5
C2—C3—H3A	119.7	C15—C16—H16B	109.5
C4—C3—H3A	119.7	H16A—C16—H16B	109.5
C18—O4—P1	123.20 (19)	C15—C16—H16C	109.5
C5—C4—C3	120.0 (3)	H16A—C16—H16C	109.5
C5—C4—H4A	120.0	H16B—C16—H16C	109.5
C3—C4—H4A	120.0	C15—C17—H17A	109.5
C6—C5—C4	120.1 (3)	C15—C17—H17B	109.5
C6—C5—H5A	119.9	H17A—C17—H17B	109.5
C4—C5—H5A	119.9	C15—C17—H17C	109.5
C5—C6—C7	119.7 (3)	H17A—C17—H17C	109.5
C5—C6—H6A	120.2	H17B—C17—H17C	109.5
C7—C6—H6A	120.2	O4—C18—C20	106.7 (3)
C2—C7—C6	121.0 (3)	O4—C18—C19	110.1 (3)
C2—C7—H7A	119.5	C20—C18—C19	113.7 (4)
C6—C7—H7A	119.5	O4—C18—H18A	108.7
N1—C8—C9	112.6 (2)	C20—C18—H18A	108.7
N1—C8—P1	112.04 (18)	C19—C18—H18A	108.7
C9—C8—P1	113.18 (19)	C18—C19—H19A	109.5
N1—C8—H8A	106.1	C18—C19—H19B	109.5
C9—C8—H8A	106.1	H19A—C19—H19B	109.5
P1—C8—H8A	106.1	C18—C19—H19C	109.5
C14—C9—C10	118.1 (3)	H19A—C19—H19C	109.5
C14—C9—C8	120.7 (3)	H19B—C19—H19C	109.5
C10—C9—C8	121.0 (2)	C18—C20—H20A	109.5
C11—C10—C9	120.5 (3)	C18—C20—H20B	109.5
C11—C10—H10A	119.7	H20A—C20—H20B	109.5
C9—C10—H10A	119.7	C18—C20—H20C	109.5
C12—C11—C10	120.5 (3)	H20A—C20—H20C	109.5
C12—C11—H11A	119.7	H20B—C20—H20C	109.5
C8—N1—C1—O1	−3.5 (4)	O2—P1—C8—N1	82.0 (2)
C8—N1—C1—C2	175.2 (2)	O3—P1—C8—N1	−40.9 (2)
O1—C1—C2—C3	6.2 (4)	O4—P1—C8—N1	−153.99 (19)
N1—C1—C2—C3	−172.5 (3)	O2—P1—C8—C9	−46.6 (2)
O1—C1—C2—C7	−174.3 (3)	O3—P1—C8—C9	−169.52 (19)
N1—C1—C2—C7	7.0 (4)	O4—P1—C8—C9	77.4 (2)
O2—P1—O3—C15	−173.2 (2)	N1—C8—C9—C14	116.7 (3)
O4—P1—O3—C15	61.0 (3)	P1—C8—C9—C14	−115.0 (3)
C8—P1—O3—C15	−45.8 (3)	N1—C8—C9—C10	−58.9 (4)
C7—C2—C3—C4	−2.5 (5)	P1—C8—C9—C10	69.4 (3)
C1—C2—C3—C4	177.0 (3)	C14—C9—C10—C11	−0.7 (5)
O2—P1—O4—C18	−19.8 (3)	C8—C9—C10—C11	174.9 (3)
O3—P1—O4—C18	102.8 (2)	C9—C10—C11—C12	1.0 (5)
C8—P1—O4—C18	−145.1 (2)	C10—C11—C12—C13	−0.4 (6)
C2—C3—C4—C5	1.4 (6)	C11—C12—C13—C14	−0.5 (6)
C3—C4—C5—C6	0.3 (6)	C10—C9—C14—C13	−0.2 (5)
C4—C5—C6—C7	−0.8 (5)	C8—C9—C14—C13	−175.8 (3)
C3—C2—C7—C6	2.0 (5)	C12—C13—C14—C9	0.8 (5)
C1—C2—C7—C6	−177.4 (3)	P1—O3—C15—C16	136.8 (3)
C5—C6—C7—C2	−0.4 (6)	P1—O3—C15—C17	−100.8 (3)
C1—N1—C8—C9	−101.9 (3)	P1—O4—C18—C20	156.8 (3)
C1—N1—C8—P1	129.2 (2)	P1—O4—C18—C19	−79.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.05	2.895 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.05	2.895 (3)	165

Symmetry code: (i) .