O,O-Di­phenyl 1-(3-phenyl­thio­ureido)­ethane­phospho­nate

The crystal structure of the title compound, C₂₁H₂₁N₂O₃PS, is reported. In the structure, centrosymmetrically related mol­ecules are linked by N—H...O hydrogen bonds and form dimers. The geometry around the P atom indicates a distorted tetrahedron.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.130
• Data-to-parameter ratio = 15.0

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEX (McArdle, 1995) and PLUTON92 (Spek, 1992); software used to prepare material for publication: PARST97 (Nardelli, 1996).

O,O-Diphenyl 1-(3-phenylthioureido)ethanephosphonate

Crystal data

C21H21N2O3PS	Z = 2
Mr = 412.43	F(000) = 432
Triclinic, P1	Dx = 1.300 Mg m^−3 Dm = 1.294 Mg m^−3 Dm measured by flotation in xylene, bromobenzene, heptane & toluene
a = 9.753 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 10.069 (1) Å	Cell parameters from 25 reflections
c = 12.255 (1) Å	θ = 22.5–30.4°
α = 98.17 (1)°	µ = 2.28 mm^−1
β = 103.37 (1)°	T = 293 K
γ = 111.63 (1)°	Prism, colourless
V = 1053.5 (2) Å^3	0.5 × 0.3 × 0.3 mm

Data collection

Rigaku AFC-5S diffractometer	2609 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
Graphite monochromator	θmax = 72.6°, θmin = 3.8°
ω scans	h = −12→11
Absorption correction: analytical (de Meulenaer & Tompa, 1965)	k = 0→12
Tmin = 0.356, Tmax = 0.619	l = −15→15
4248 measured reflections	3 standard reflections every 150 reflections
3996 independent reflections	intensity decay: <2%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.051	w = 1/[σ^2(Fo^2) + (0.0837P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.37 e Å^−3
3995 reflections	Δρmin = −0.51 e Å^−3
267 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0125 (10)
Primary atom site location: structure-invariant direct methods

Special details

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 on F² for ALL reflections except for 1 with very negative F² or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.37994 (8)	0.06954 (7)	0.19273 (6)	0.0646 (2)
C1	0.4535 (3)	0.2475 (3)	0.2626 (2)	0.0514 (6)
N1	0.5642 (3)	0.3582 (3)	0.2393 (2)	0.0616 (6)
H1	0.574 (3)	0.447 (3)	0.274 (2)	0.069 (8)*
N2	0.4071 (3)	0.2969 (3)	0.3492 (2)	0.0588 (6)
H2	0.444 (3)	0.390 (3)	0.373 (2)	0.062 (8)*
C2	0.2823 (3)	0.2059 (3)	0.3875 (2)	0.0575 (6)
H201	0.262 (3)	0.099 (3)	0.345 (2)	0.058 (7)*
C3	0.1441 (3)	0.2447 (4)	0.3585 (3)	0.0814 (9)
H301	0.0645 (11)	0.1837 (17)	0.3860 (18)	0.122*
H302	0.1048 (16)	0.228 (2)	0.2761 (3)	0.122*
H303	0.1756 (7)	0.3466 (7)	0.3951 (16)	0.122*
P1	0.36202 (8)	0.23343 (7)	0.54149 (6)	0.0561 (2)
O1	0.4222 (2)	0.3870 (2)	0.6077 (2)	0.0660 (5)
O2	0.2247 (2)	0.1198 (2)	0.57135 (14)	0.0631 (5)
O3	0.4843 (2)	0.1648 (2)	0.5597 (2)	0.0653 (5)
C11	0.6430 (3)	0.3498 (3)	0.1567 (2)	0.0555 (6)
C12	0.7014 (3)	0.2458 (3)	0.1408 (2)	0.0642 (7)
H12	0.6874 (3)	0.1756 (3)	0.1839 (2)	0.077*
C13	0.7802 (3)	0.2454 (3)	0.0616 (3)	0.0751 (8)
H13	0.8179 (3)	0.1738 (3)	0.0503 (3)	0.090*
C14	0.8040 (4)	0.3496 (4)	−0.0014 (3)	0.0841 (10)
H14	0.8567 (4)	0.3481 (4)	−0.0555 (3)	0.101*
C15	0.7500 (4)	0.4552 (4)	0.0158 (3)	0.0863 (10)
H15	0.7678 (4)	0.5271 (4)	−0.0256 (3)	0.104*
C16	0.6685 (3)	0.4563 (3)	0.0948 (2)	0.0708 (8)
H16	0.6313 (3)	0.5283 (3)	0.1059 (2)	0.085*
C21	0.2160 (3)	0.1294 (3)	0.6864 (2)	0.0566 (6)
C22	0.0865 (3)	0.1380 (3)	0.7057 (2)	0.0669 (7)
H22	0.0104 (3)	0.1418 (3)	0.6460 (2)	0.080*
C23	0.0702 (4)	0.1411 (4)	0.8150 (3)	0.0809 (9)
H23	−0.0166 (4)	0.1480 (4)	0.8298 (3)	0.097*
C24	0.1840 (4)	0.1339 (4)	0.9022 (3)	0.0825 (9)
H24	0.1736 (4)	0.1354 (4)	0.9758 (3)	0.099*
C25	0.3115 (4)	0.1244 (3)	0.8804 (3)	0.0818 (9)
H25	0.3875 (4)	0.1201 (3)	0.9399 (3)	0.098*
C26	0.3302 (3)	0.1212 (3)	0.7718 (3)	0.0698 (7)
H26	0.4167 (3)	0.1138 (3)	0.7569 (3)	0.084*
C31	0.6437 (3)	0.2453 (3)	0.5773 (2)	0.0596 (6)
C32	0.7361 (4)	0.3422 (4)	0.6820 (3)	0.0803 (9)
H32	0.6941 (4)	0.3573 (4)	0.7410 (3)	0.096*
C33	0.8916 (4)	0.4164 (4)	0.6986 (3)	0.0980 (11)
H33	0.9560 (4)	0.4813 (4)	0.7698 (3)	0.118*
C34	0.9525 (4)	0.3957 (5)	0.6110 (4)	0.1060 (13)
H34	1.0577 (4)	0.4480 (5)	0.6220 (4)	0.127*
C35	0.8579 (4)	0.2975 (5)	0.5071 (4)	0.0991 (12)
H35	0.8989 (4)	0.2832 (5)	0.4474 (4)	0.119*
C36	0.7016 (3)	0.2196 (4)	0.4906 (3)	0.0734 (8)
H36	0.6375 (3)	0.1507 (4)	0.4210 (3)	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0710 (4)	0.0543 (4)	0.0614 (4)	0.0187 (3)	0.0255 (3)	0.0050 (3)
C1	0.0541 (14)	0.0540 (14)	0.0481 (12)	0.0229 (11)	0.0192 (11)	0.0121 (10)
N1	0.0731 (14)	0.0531 (13)	0.0630 (13)	0.0234 (11)	0.0355 (11)	0.0117 (10)
N2	0.0683 (14)	0.0491 (13)	0.0615 (12)	0.0196 (11)	0.0338 (11)	0.0116 (10)
C2	0.0602 (15)	0.0553 (15)	0.0623 (15)	0.0223 (12)	0.0296 (12)	0.0174 (12)
C3	0.072 (2)	0.098 (2)	0.092 (2)	0.043 (2)	0.034 (2)	0.036 (2)
P1	0.0602 (4)	0.0488 (4)	0.0612 (4)	0.0188 (3)	0.0292 (3)	0.0133 (3)
O1	0.0794 (12)	0.0465 (10)	0.0714 (11)	0.0192 (9)	0.0378 (10)	0.0082 (8)
O2	0.0626 (11)	0.0607 (10)	0.0605 (10)	0.0146 (9)	0.0272 (8)	0.0165 (8)
O3	0.0588 (10)	0.0545 (10)	0.0825 (12)	0.0224 (8)	0.0237 (9)	0.0167 (9)
C11	0.0581 (14)	0.0539 (14)	0.0489 (13)	0.0163 (12)	0.0208 (11)	0.0088 (11)
C12	0.071 (2)	0.061 (2)	0.0627 (15)	0.0260 (13)	0.0276 (13)	0.0128 (12)
C13	0.075 (2)	0.075 (2)	0.074 (2)	0.026 (2)	0.035 (2)	0.0070 (15)
C14	0.092 (2)	0.092 (2)	0.068 (2)	0.027 (2)	0.046 (2)	0.011 (2)
C15	0.106 (3)	0.087 (2)	0.077 (2)	0.034 (2)	0.050 (2)	0.034 (2)
C16	0.083 (2)	0.069 (2)	0.068 (2)	0.030 (2)	0.036 (2)	0.0236 (14)
C21	0.0601 (15)	0.0523 (14)	0.0593 (14)	0.0188 (11)	0.0261 (12)	0.0194 (11)
C22	0.064 (2)	0.071 (2)	0.070 (2)	0.0274 (14)	0.0250 (14)	0.0261 (14)
C23	0.084 (2)	0.087 (2)	0.086 (2)	0.036 (2)	0.047 (2)	0.026 (2)
C24	0.104 (3)	0.079 (2)	0.065 (2)	0.031 (2)	0.036 (2)	0.025 (2)
C25	0.091 (2)	0.078 (2)	0.068 (2)	0.029 (2)	0.015 (2)	0.029 (2)
C26	0.064 (2)	0.072 (2)	0.079 (2)	0.0282 (14)	0.0237 (15)	0.0299 (15)
C31	0.0562 (15)	0.059 (2)	0.066 (2)	0.0238 (12)	0.0187 (12)	0.0215 (12)
C32	0.077 (2)	0.084 (2)	0.066 (2)	0.027 (2)	0.0115 (15)	0.016 (2)
C33	0.071 (2)	0.090 (3)	0.102 (3)	0.019 (2)	−0.005 (2)	0.026 (2)
C34	0.059 (2)	0.111 (3)	0.148 (4)	0.033 (2)	0.015 (2)	0.068 (3)
C35	0.081 (2)	0.139 (3)	0.121 (3)	0.068 (2)	0.053 (2)	0.065 (3)
C36	0.068 (2)	0.093 (2)	0.074 (2)	0.047 (2)	0.0233 (15)	0.025 (2)

Geometric parameters (Å, º)

S1—C1	1.671 (2)	C15—C16	1.388 (4)
C1—N2	1.347 (3)	C15—H15	0.93
C1—N1	1.355 (3)	C16—H16	0.93
N1—C11	1.416 (3)	C21—C22	1.368 (4)
N1—H1	0.90 (3)	C21—C26	1.377 (4)
N2—C2	1.451 (3)	C22—C23	1.383 (4)
N2—H2	0.85 (3)	C22—H22	0.93
C2—C3	1.517 (4)	C23—C24	1.383 (5)
C2—P1	1.805 (3)	C23—H23	0.93
C2—H201	1.05 (2)	C24—C25	1.364 (4)
C3—H301	0.96	C24—H24	0.93
C3—H302	0.96	C25—C26	1.382 (4)
C3—H303	0.96	C25—H25	0.93
P1—O1	1.465 (2)	C26—H26	0.93
P1—O2	1.566 (2)	C31—C36	1.349 (4)
P1—O3	1.574 (2)	C31—C32	1.368 (4)
O2—C21	1.423 (3)	C32—C33	1.370 (4)
O3—C31	1.410 (3)	C32—H32	0.93
C11—C12	1.375 (4)	C33—C34	1.367 (5)
C11—C16	1.382 (4)	C33—H33	0.93
C12—C13	1.372 (3)	C34—C35	1.371 (6)
C12—H12	0.93	C34—H34	0.93
C13—C14	1.373 (5)	C35—C36	1.382 (4)
C13—H13	0.93	C35—H35	0.93
C14—C15	1.360 (5)	C36—H36	0.93
C14—H14	0.93
N2—C1—N1	112.3 (2)	C14—C15—H15	119.8
N2—C1—S1	123.0 (2)	C16—C15—H15	119.8
N1—C1—S1	124.7 (2)	C11—C16—C15	119.6 (3)
C1—N1—C11	128.9 (2)	C11—C16—H16	120.2
C1—N1—H1	111.8 (17)	C15—C16—H16	120.2
C11—N1—H1	118.4 (17)	C22—C21—C26	122.3 (2)
C1—N2—C2	124.8 (2)	C22—C21—O2	117.3 (2)
C1—N2—H2	115.3 (17)	C26—C21—O2	120.4 (2)
C2—N2—H2	118.9 (17)	C21—C22—C23	119.2 (3)
N2—C2—C3	111.6 (2)	C21—C22—H22	120.4
N2—C2—P1	106.6 (2)	C23—C22—H22	120.4
C3—C2—P1	111.9 (2)	C24—C23—C22	119.4 (3)
N2—C2—H201	101.8 (13)	C24—C23—H23	120.3
C3—C2—H201	114.9 (13)	C22—C23—H23	120.3
P1—C2—H201	109.3 (13)	C25—C24—C23	120.2 (3)
C2—C3—H301	109.5	C25—C24—H24	119.9
C2—C3—H302	109.5	C23—C24—H24	119.9
H301—C3—H302	109.5	C24—C25—C26	121.3 (3)
C2—C3—H303	109.5	C24—C25—H25	119.3
H301—C3—H303	109.5	C26—C25—H25	119.3
H302—C3—H303	109.5	C21—C26—C25	117.6 (3)
O1—P1—O2	115.69 (10)	C21—C26—H26	121.2
O1—P1—O3	114.08 (11)	C25—C26—H26	121.2
O2—P1—O3	102.22 (10)	C36—C31—C32	121.9 (3)
O1—P1—C2	113.74 (12)	C36—C31—O3	118.4 (3)
O2—P1—C2	102.43 (11)	C32—C31—O3	119.7 (2)
O3—P1—C2	107.37 (11)	C31—C32—C33	118.9 (3)
C21—O2—P1	122.5 (2)	C31—C32—H32	120.6
C31—O3—P1	123.9 (2)	C33—C32—H32	120.6
C12—C11—C16	119.5 (2)	C34—C33—C32	120.4 (4)
C12—C11—N1	122.7 (2)	C34—C33—H33	119.8
C16—C11—N1	117.7 (2)	C32—C33—H33	119.8
C13—C12—C11	120.1 (3)	C33—C34—C35	119.7 (3)
C13—C12—H12	119.95	C33—C34—H34	120.2
C11—C12—H12	119.95	C35—C34—H34	120.2
C12—C13—C14	120.6 (3)	C34—C35—C36	120.3 (4)
C12—C13—H13	119.7	C34—C35—H35	119.9
C14—C13—H13	119.7	C36—C35—H35	119.9
C15—C14—C13	119.6 (3)	C31—C36—C35	118.8 (3)
C15—C14—H14	120.2	C31—C36—H36	120.6
C13—C14—H14	120.2	C35—C36—H36	120.6
C14—C15—C16	120.5 (3)
N2—C1—N1—C11	178.6 (3)	C13—C14—C15—C16	−1.3 (5)
S1—C1—N1—C11	−1.8 (4)	C12—C11—C16—C15	1.2 (4)
N1—C1—N2—C2	175.2 (2)	N1—C11—C16—C15	177.8 (3)
S1—C1—N2—C2	−4.4 (4)	C14—C15—C16—C11	0.4 (5)
C1—N2—C2—C3	−111.4 (3)	P1—O2—C21—C22	123.0 (2)
C1—N2—C2—P1	126.2 (2)	P1—O2—C21—C26	−60.7 (3)
N2—C2—P1—O1	59.9 (2)	C26—C21—C22—C23	1.0 (4)
C3—C2—P1—O1	−62.3 (2)	O2—C21—C22—C23	177.2 (2)
N2—C2—P1—O2	−174.5 (2)	C21—C22—C23—C24	−0.6 (5)
C3—C2—P1—O2	63.2 (2)	C22—C23—C24—C25	0.3 (5)
N2—C2—P1—O3	−67.3 (2)	C23—C24—C25—C26	−0.3 (5)
C3—C2—P1—O3	170.5 (2)	C22—C21—C26—C25	−1.0 (4)
O1—P1—O2—C21	−37.3 (2)	O2—C21—C26—C25	−177.1 (2)
O3—P1—O2—C21	87.2 (2)	C24—C25—C26—C21	0.6 (5)
C2—P1—O2—C21	−161.6 (2)	P1—O3—C31—C36	−107.9 (3)
O1—P1—O3—C31	−34.7 (2)	P1—O3—C31—C32	74.6 (3)
O2—P1—O3—C31	−160.3 (2)	C36—C31—C32—C33	0.8 (5)
C2—P1—O3—C31	92.3 (2)	O3—C31—C32—C33	178.2 (3)
C1—N1—C11—C12	−44.5 (4)	C31—C32—C33—C34	1.1 (6)
C1—N1—C11—C16	139.0 (3)	C32—C33—C34—C35	−1.5 (6)
C16—C11—C12—C13	−1.9 (4)	C33—C34—C35—C36	0.0 (6)
N1—C11—C12—C13	−178.3 (3)	C32—C31—C36—C35	−2.3 (5)
C11—C12—C13—C14	1.0 (4)	O3—C31—C36—C35	−179.7 (3)
C12—C13—C14—C15	0.6 (5)	C34—C35—C36—C31	1.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.90 (3)	2.03 (3)	2.896 (3)	161 (3)
N2—H2···O1^i	0.85 (3)	2.08 (3)	2.897 (3)	160 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.