Diphenyl (2-chloro-benzyl-amido)-phosphate.

In the title compound, C(19)H(17)ClNO(3)P, the P atom exhibits a distorted tetra-hedral configuration. In the crystal, pairs of inter-molecular N-H⋯O(P) hydrogen bonds form centrosymmetric dimers.

Related literature

For related structures, see: Pourayoubi & Zargaran (2010 ▶); Pourayoubi et al. (2010 ▶).

Experimental

Crystal data

C19H17ClNO3P

M = 373.76

Triclinic,

a = 8.6178 (5) Å

b = 9.5901 (6) Å

c = 12.1543 (7) Å

α = 107.609 (1)°

β = 93.882 (1)°

γ = 110.036 (1)°

V = 882.86 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.40 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.881, T max = 0.923

13560 measured reflections

3982 independent reflections

3681 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.02

3982 reflections

230 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004955X/lh5173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004955X/lh5173Isup2.hkl

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

C19H17ClNO3P	Z = 2
Mr = 373.76	F(000) = 388
Triclinic, P1	Dx = 1.406 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6178 (5) Å	Cell parameters from 9988 reflections
b = 9.5901 (6) Å	θ = 2.4–28.0°
c = 12.1543 (7) Å	µ = 0.33 mm−1
α = 107.609 (1)°	T = 100 K
β = 93.882 (1)°	Block, colourless
γ = 110.036 (1)°	0.40 × 0.35 × 0.25 mm
V = 882.86 (9) Å3

Bruker APEXII CCD diffractometer	3982 independent reflections
Radiation source: fine-focus sealed tube	3681 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 28.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→10
Tmin = 0.881, Tmax = 0.923	k = −11→12
13560 measured reflections	l = −15→11

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.4993P] where P = (Fo2 + 2Fc2)/3
3982 reflections	(Δ/σ)max = 0.004
230 parameters	Δρmax = 0.28 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
Cl1	1.12274 (4)	0.65811 (4)	0.77058 (3)	0.02847 (10)
P1	0.49017 (4)	0.15695 (4)	0.67814 (3)	0.01573 (9)
O1	0.35884 (12)	0.01133 (11)	0.59500 (8)	0.0201 (2)
O2	0.44078 (12)	0.30686 (11)	0.72227 (8)	0.01837 (19)
O3	0.53917 (12)	0.14595 (11)	0.80359 (8)	0.0184 (2)
N1	0.65627 (15)	0.21809 (13)	0.62570 (10)	0.0194 (2)
C1	0.97088 (17)	0.61883 (16)	0.65109 (11)	0.0190 (3)
C2	1.00000 (19)	0.72582 (16)	0.59229 (13)	0.0244 (3)
H2A	1.1015	0.8170	0.6159	0.029*
C3	0.8788 (2)	0.69789 (18)	0.49836 (13)	0.0276 (3)
H3A	0.8965	0.7708	0.4577	0.033*
C4	0.7317 (2)	0.56346 (18)	0.46398 (13)	0.0262 (3)
H4A	0.6485	0.5443	0.3999	0.031*
C5	0.70658 (17)	0.45701 (16)	0.52345 (12)	0.0207 (3)
H5A	0.6058	0.3650	0.4989	0.025*
C6	0.82539 (16)	0.48181 (15)	0.61804 (11)	0.0167 (2)
C7	0.80201 (17)	0.36547 (15)	0.68278 (11)	0.0188 (3)
H7A	0.9043	0.3410	0.6882	0.023*
H7B	0.7890	0.4157	0.7639	0.023*
C8	0.32185 (16)	0.31673 (15)	0.79467 (11)	0.0170 (3)
C9	0.35893 (18)	0.46128 (16)	0.88220 (12)	0.0206 (3)
H9A	0.4608	0.5481	0.8920	0.025*
C10	0.24451 (19)	0.47717 (17)	0.95549 (12)	0.0232 (3)
H10A	0.2686	0.5755	1.0163	0.028*
C11	0.09537 (19)	0.35066 (17)	0.94059 (13)	0.0235 (3)
H11A	0.0181	0.3619	0.9915	0.028*
C12	0.05959 (18)	0.20772 (17)	0.85097 (13)	0.0241 (3)
H12A	−0.0430	0.1213	0.8402	0.029*
C13	0.17259 (18)	0.18976 (16)	0.77676 (12)	0.0215 (3)
H13A	0.1478	0.0921	0.7149	0.026*
C14	0.60296 (16)	0.03684 (15)	0.82152 (12)	0.0177 (3)
C15	0.60994 (18)	−0.08832 (16)	0.73025 (13)	0.0233 (3)
H15A	0.5699	−0.1047	0.6508	0.028*
C16	0.67701 (19)	−0.18925 (17)	0.75786 (14)	0.0277 (3)
H16A	0.6826	−0.2756	0.6965	0.033*
C17	0.7356 (2)	−0.16551 (18)	0.87353 (15)	0.0287 (3)
H17A	0.7817	−0.2348	0.8913	0.034*
C18	0.7269 (2)	−0.03992 (19)	0.96360 (14)	0.0278 (3)
H18A	0.7667	−0.0235	1.0431	0.033*
C19	0.65988 (18)	0.06176 (16)	0.93767 (12)	0.0214 (3)
H19A	0.6533	0.1475	0.9991	0.026*
H1N	0.661 (2)	0.160 (2)	0.5644 (18)	0.031 (5)*

	U11	U22	U33	U12	U13	U23
Cl1	0.02121 (18)	0.0312 (2)	0.02217 (17)	0.00205 (14)	−0.00251 (13)	0.00503 (14)
P1	0.01745 (17)	0.01436 (16)	0.01548 (16)	0.00594 (13)	0.00454 (12)	0.00518 (12)
O1	0.0195 (5)	0.0182 (5)	0.0192 (4)	0.0047 (4)	0.0049 (4)	0.0043 (4)
O2	0.0209 (5)	0.0169 (4)	0.0210 (4)	0.0091 (4)	0.0081 (4)	0.0086 (4)
O3	0.0242 (5)	0.0170 (4)	0.0164 (4)	0.0107 (4)	0.0044 (4)	0.0056 (3)
N1	0.0207 (6)	0.0157 (5)	0.0184 (5)	0.0048 (4)	0.0074 (5)	0.0029 (4)
C1	0.0186 (6)	0.0199 (6)	0.0170 (6)	0.0080 (5)	0.0041 (5)	0.0036 (5)
C2	0.0262 (7)	0.0184 (6)	0.0290 (7)	0.0072 (6)	0.0116 (6)	0.0088 (5)
C3	0.0369 (8)	0.0268 (7)	0.0302 (7)	0.0179 (7)	0.0142 (7)	0.0170 (6)
C4	0.0302 (8)	0.0322 (8)	0.0235 (7)	0.0178 (6)	0.0053 (6)	0.0128 (6)
C5	0.0198 (6)	0.0218 (6)	0.0201 (6)	0.0088 (5)	0.0032 (5)	0.0059 (5)
C6	0.0181 (6)	0.0166 (6)	0.0166 (6)	0.0086 (5)	0.0054 (5)	0.0049 (5)
C7	0.0178 (6)	0.0189 (6)	0.0188 (6)	0.0054 (5)	0.0025 (5)	0.0072 (5)
C8	0.0190 (6)	0.0198 (6)	0.0173 (6)	0.0109 (5)	0.0048 (5)	0.0091 (5)
C9	0.0211 (7)	0.0179 (6)	0.0223 (6)	0.0072 (5)	0.0035 (5)	0.0068 (5)
C10	0.0289 (7)	0.0217 (7)	0.0209 (6)	0.0132 (6)	0.0057 (6)	0.0056 (5)
C11	0.0259 (7)	0.0295 (7)	0.0249 (7)	0.0171 (6)	0.0107 (6)	0.0140 (6)
C12	0.0199 (7)	0.0238 (7)	0.0315 (7)	0.0085 (5)	0.0084 (6)	0.0125 (6)
C13	0.0217 (7)	0.0185 (6)	0.0238 (7)	0.0085 (5)	0.0050 (5)	0.0056 (5)
C14	0.0161 (6)	0.0162 (6)	0.0225 (6)	0.0057 (5)	0.0050 (5)	0.0092 (5)
C15	0.0257 (7)	0.0201 (6)	0.0231 (7)	0.0103 (6)	0.0016 (5)	0.0049 (5)
C16	0.0281 (8)	0.0198 (7)	0.0352 (8)	0.0120 (6)	0.0052 (6)	0.0066 (6)
C17	0.0272 (8)	0.0265 (7)	0.0410 (9)	0.0138 (6)	0.0075 (7)	0.0193 (7)
C18	0.0297 (8)	0.0339 (8)	0.0279 (7)	0.0142 (6)	0.0068 (6)	0.0190 (6)
C19	0.0230 (7)	0.0229 (7)	0.0214 (6)	0.0094 (5)	0.0080 (5)	0.0102 (5)

Cl1—C1	1.7429 (14)	C8—C9	1.3834 (18)
P1—O1	1.4699 (10)	C8—C13	1.3831 (19)
P1—O2	1.5872 (9)	C9—C10	1.389 (2)
P1—O3	1.5984 (9)	C9—H9A	0.9500
P1—N1	1.6042 (12)	C10—C11	1.387 (2)
O2—C8	1.4043 (15)	C10—H10A	0.9500
O3—C14	1.4002 (15)	C11—C12	1.386 (2)
N1—C7	1.4591 (17)	C11—H11A	0.9500
N1—H1N	0.80 (2)	C12—C13	1.390 (2)
C1—C2	1.3850 (19)	C12—H12A	0.9500
C1—C6	1.3942 (18)	C13—H13A	0.9500
C2—C3	1.389 (2)	C14—C19	1.3829 (19)
C2—H2A	0.9500	C14—C15	1.3884 (19)
C3—C4	1.388 (2)	C15—C16	1.392 (2)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.388 (2)	C16—C17	1.384 (2)
C4—H4A	0.9500	C16—H16A	0.9500
C5—C6	1.3910 (18)	C17—C18	1.389 (2)
C5—H5A	0.9500	C17—H17A	0.9500
C6—C7	1.5175 (17)	C18—C19	1.389 (2)
C7—H7A	0.9900	C18—H18A	0.9500
C7—H7B	0.9900	C19—H19A	0.9500
O1—P1—O2	116.37 (6)	C9—C8—O2	116.66 (12)
O1—P1—O3	113.92 (5)	C13—C8—O2	121.59 (12)
O2—P1—O3	98.03 (5)	C8—C9—C10	118.77 (13)
O1—P1—N1	113.05 (6)	C8—C9—H9A	120.6
O2—P1—N1	104.00 (6)	C10—C9—H9A	120.6
O3—P1—N1	110.13 (6)	C11—C10—C9	120.55 (13)
C8—O2—P1	123.42 (8)	C11—C10—H10A	119.7
C14—O3—P1	124.66 (8)	C9—C10—H10A	119.7
C7—N1—P1	125.99 (9)	C12—C11—C10	119.65 (13)
C7—N1—H1N	117.4 (14)	C12—C11—H11A	120.2
P1—N1—H1N	116.5 (14)	C10—C11—H11A	120.2
C2—C1—C6	122.43 (13)	C11—C12—C13	120.56 (14)
C2—C1—Cl1	118.35 (11)	C11—C12—H12A	119.7
C6—C1—Cl1	119.22 (10)	C13—C12—H12A	119.7
C1—C2—C3	119.07 (13)	C8—C13—C12	118.73 (13)
C1—C2—H2A	120.5	C8—C13—H13A	120.6
C3—C2—H2A	120.5	C12—C13—H13A	120.6
C4—C3—C2	119.95 (13)	C19—C14—C15	121.49 (12)
C4—C3—H3A	120.0	C19—C14—O3	115.36 (11)
C2—C3—H3A	120.0	C15—C14—O3	123.15 (12)
C3—C4—C5	119.83 (14)	C14—C15—C16	118.46 (13)
C3—C4—H4A	120.1	C14—C15—H15A	120.8
C5—C4—H4A	120.1	C16—C15—H15A	120.8
C4—C5—C6	121.60 (13)	C17—C16—C15	120.86 (14)
C4—C5—H5A	119.2	C17—C16—H16A	119.6
C6—C5—H5A	119.2	C15—C16—H16A	119.6
C5—C6—C1	117.10 (12)	C16—C17—C18	119.76 (13)
C5—C6—C7	122.47 (12)	C16—C17—H17A	120.1
C1—C6—C7	120.42 (12)	C18—C17—H17A	120.1
N1—C7—C6	113.03 (11)	C19—C18—C17	120.15 (14)
N1—C7—H7A	109.0	C19—C18—H18A	119.9
C6—C7—H7A	109.0	C17—C18—H18A	119.9
N1—C7—H7B	109.0	C14—C19—C18	119.28 (13)
C6—C7—H7B	109.0	C14—C19—H19A	120.4
H7A—C7—H7B	107.8	C18—C19—H19A	120.4
C9—C8—C13	121.71 (13)
O1—P1—O2—C8	67.62 (11)	C1—C6—C7—N1	−171.04 (11)
O3—P1—O2—C8	−54.18 (10)	P1—O2—C8—C9	140.36 (10)
N1—P1—O2—C8	−167.34 (10)	P1—O2—C8—C13	−41.74 (16)
O1—P1—O3—C14	59.85 (11)	C13—C8—C9—C10	1.6 (2)
O2—P1—O3—C14	−176.56 (10)	O2—C8—C9—C10	179.53 (11)
N1—P1—O3—C14	−68.38 (11)	C8—C9—C10—C11	−0.4 (2)
O1—P1—N1—C7	174.57 (10)	C9—C10—C11—C12	−0.7 (2)
O2—P1—N1—C7	47.45 (12)	C10—C11—C12—C13	0.6 (2)
O3—P1—N1—C7	−56.72 (12)	C9—C8—C13—C12	−1.7 (2)
C6—C1—C2—C3	1.3 (2)	O2—C8—C13—C12	−179.47 (12)
Cl1—C1—C2—C3	−178.73 (11)	C11—C12—C13—C8	0.5 (2)
C1—C2—C3—C4	−0.6 (2)	P1—O3—C14—C19	171.04 (10)
C2—C3—C4—C5	−0.2 (2)	P1—O3—C14—C15	−8.87 (18)
C3—C4—C5—C6	0.4 (2)	C19—C14—C15—C16	−0.4 (2)
C4—C5—C6—C1	0.29 (19)	O3—C14—C15—C16	179.53 (13)
C4—C5—C6—C7	−178.79 (12)	C14—C15—C16—C17	−0.1 (2)
C2—C1—C6—C5	−1.16 (19)	C15—C16—C17—C18	0.4 (2)
Cl1—C1—C6—C5	178.91 (10)	C16—C17—C18—C19	−0.2 (2)
C2—C1—C6—C7	177.94 (12)	C15—C14—C19—C18	0.5 (2)
Cl1—C1—C6—C7	−1.99 (17)	O3—C14—C19—C18	−179.36 (12)
P1—N1—C7—C6	−113.96 (12)	C17—C18—C19—C14	−0.3 (2)
C5—C6—C7—N1	8.01 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.80 (2)	2.08 (2)	2.8703 (15)	172.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.80 (2)	2.08 (2)	2.8703 (15)	172.2 (19)

Symmetry code: (i) .