N,N'-Dibenzyl-N,N'-dimethyl-N''-(methyl-sulfon-yl)phospho-ric triamide.

In the title compound, C(17)H(24)N(3)O(3)PS, the P and the S atoms are each in a distorted tetra-hedral environment and the N atoms display sp(2) character. The phosphoryl group and the NH unit are anti with respect to one another. The dihedral angle between the mean planes of the benzene rings is 31.08 (8)°. The crystal packing is stabilized by N-H⋯O hydrogen bonds, forming an extended chain parallel to the b axis.

Related literature

For phospho­ramidates having a P(O)[N(CH3)(CH2C6H5)]2 moiety, see: Pourayoubi et al. (2010 ▶); Gholivand et al. (2005 ▶). For bond lengths in a <span class="Chemical">sulfonamide compound, see: Ibrahim et al. (2011 ▶) and references cited therein.

Experimental

Crystal data

C17H24N3O3PS

M = 381.42

Orthorhombic,

a = 8.5343 (4) Å

b = 10.1800 (5) Å

c = 22.0455 (10) Å

V = 1915.29 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.47 × 0.38 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.700, T max = 0.746

65627 measured reflections

4155 independent reflections

3937 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.094

S = 1.08

4155 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1769 Friedel pairs

Flack parameter: 0.02 (7)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; 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 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811015832/jj2084sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811015832/jj2084Isup2.hkl

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

C17H24N3O3PS	F(000) = 808
Mr = 381.42	Dx = 1.323 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9705 reflections
a = 8.5343 (4) Å	θ = 2.6–29.5°
b = 10.1800 (5) Å	µ = 0.27 mm−1
c = 22.0455 (10) Å	T = 296 K
V = 1915.29 (16) Å3	Irregular, colourless
Z = 4	0.47 × 0.38 × 0.30 mm

Bruker APEXII CCD diffractometer	4155 independent reflections
Radiation source: fine-focus sealed tube	3937 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.700, Tmax = 0.746	k = −13→13
65627 measured reflections	l = −28→28

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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0564P)2 + 0.4498P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
4155 reflections	Δρmax = 0.30 e Å−3
226 parameters	Δρmin = −0.22 e Å−3
0 restraints	Absolute structure: Flack (1983), 1769 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.02 (7)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
S	−0.14987 (6)	0.66473 (5)	0.33606 (2)	0.03622 (13)
P	0.01450 (6)	0.58351 (4)	0.22593 (2)	0.02755 (11)
O2	−0.1835 (2)	0.78944 (16)	0.36311 (8)	0.0531 (5)
O3	−0.2779 (2)	0.58363 (18)	0.31763 (9)	0.0548 (4)
O1	0.0074 (2)	0.45080 (12)	0.25313 (7)	0.0376 (3)
N2	−0.1005 (2)	0.61222 (17)	0.16850 (8)	0.0374 (4)
N1	0.19197 (19)	0.61606 (16)	0.20271 (8)	0.0357 (4)
C16	−0.2309 (3)	0.7047 (3)	0.16690 (14)	0.0598 (7)
H16A	−0.2367	0.7506	0.2049	0.090*
H16B	−0.3268	0.6577	0.1601	0.090*
H16C	−0.2149	0.7666	0.1346	0.090*
C11	−0.4106 (4)	0.2282 (3)	0.07992 (17)	0.0756 (10)
H11	−0.4817	0.1609	0.0724	0.091*
C10	−0.3104 (4)	0.2678 (3)	0.03513 (15)	0.0733 (9)
H10	−0.3123	0.2269	−0.0026	0.088*
C9	−0.2056 (3)	0.3697 (3)	0.04626 (12)	0.0551 (6)
H9	−0.1402	0.3989	0.0154	0.066*
C14	−0.1979 (2)	0.4282 (2)	0.10302 (9)	0.0377 (4)
C15	−0.0776 (3)	0.5341 (2)	0.11360 (10)	0.0420 (5)
H15A	0.0251	0.4935	0.1155	0.050*
H15B	−0.0780	0.5928	0.0789	0.050*
C7	0.2255 (3)	0.7384 (2)	0.17023 (13)	0.0479 (6)
H7A	0.2714	0.8007	0.1984	0.058*
H7B	0.1277	0.7753	0.1558	0.058*
C6	0.3355 (2)	0.7211 (2)	0.11683 (10)	0.0370 (4)
C1	0.4198 (3)	0.8292 (2)	0.09625 (11)	0.0451 (5)
H1	0.4106	0.9094	0.1161	0.054*
C2	0.5174 (3)	0.8180 (3)	0.04622 (12)	0.0553 (6)
H2	0.5729	0.8907	0.0324	0.066*
C3	0.5322 (3)	0.6990 (3)	0.01694 (11)	0.0621 (7)
H3	0.5980	0.6912	−0.0165	0.074*
N3	−0.0373 (2)	0.69410 (14)	0.27825 (7)	0.0313 (3)
H	−0.0016	0.7726	0.2742	0.038*
C17	−0.0341 (4)	0.5731 (3)	0.38565 (11)	0.0583 (7)
H17A	0.0536	0.6251	0.3986	0.087*
H17B	0.0031	0.4958	0.3653	0.087*
H17C	−0.0952	0.5480	0.4203	0.087*
C8	0.3248 (3)	0.5572 (3)	0.23501 (12)	0.0588 (7)
H8A	0.2915	0.4778	0.2546	0.088*
H8B	0.3631	0.6179	0.2649	0.088*
H8C	0.4069	0.5375	0.2067	0.088*
C5	0.3510 (3)	0.6022 (2)	0.08697 (10)	0.0448 (5)
H5	0.2952	0.5292	0.1002	0.054*
C4	0.4499 (3)	0.5922 (3)	0.03725 (11)	0.0578 (6)
H4	0.4604	0.5120	0.0175	0.069*
C13	−0.2991 (3)	0.3855 (2)	0.14752 (11)	0.0478 (5)
H13	−0.2951	0.4233	0.1859	0.057*
C12	−0.4069 (3)	0.2868 (3)	0.13576 (15)	0.0633 (8)
H12	−0.4766	0.2604	0.1658	0.076*

	U11	U22	U33	U12	U13	U23
S	0.0438 (3)	0.0249 (2)	0.0400 (2)	−0.0002 (2)	0.0118 (2)	0.00027 (19)
P	0.0334 (2)	0.01673 (19)	0.0325 (2)	−0.00014 (17)	0.00382 (18)	−0.00090 (16)
O2	0.0683 (12)	0.0342 (8)	0.0568 (9)	0.0053 (8)	0.0255 (9)	−0.0081 (7)
O3	0.0429 (8)	0.0435 (9)	0.0780 (12)	−0.0137 (8)	0.0150 (8)	−0.0002 (8)
O1	0.0544 (8)	0.0169 (6)	0.0414 (7)	−0.0007 (6)	0.0042 (7)	−0.0001 (5)
N2	0.0398 (9)	0.0332 (9)	0.0393 (8)	0.0046 (7)	−0.0017 (7)	−0.0013 (7)
N1	0.0336 (8)	0.0301 (8)	0.0433 (9)	0.0012 (7)	0.0082 (7)	−0.0015 (7)
C16	0.0598 (15)	0.0479 (13)	0.0715 (17)	0.0193 (12)	−0.0217 (14)	−0.0054 (13)
C11	0.083 (2)	0.0558 (17)	0.088 (2)	−0.0198 (16)	−0.0378 (19)	0.0022 (16)
C10	0.092 (2)	0.0602 (17)	0.0673 (18)	0.0035 (17)	−0.0323 (18)	−0.0242 (15)
C9	0.0606 (15)	0.0588 (15)	0.0460 (12)	0.0044 (12)	−0.0048 (11)	−0.0095 (11)
C14	0.0360 (10)	0.0378 (10)	0.0394 (10)	0.0035 (9)	−0.0055 (8)	−0.0014 (8)
C15	0.0426 (11)	0.0498 (12)	0.0335 (10)	−0.0064 (10)	0.0038 (9)	−0.0025 (9)
C7	0.0481 (12)	0.0276 (10)	0.0681 (15)	−0.0014 (9)	0.0255 (12)	−0.0040 (10)
C6	0.0321 (10)	0.0344 (10)	0.0445 (11)	0.0045 (8)	0.0053 (9)	0.0037 (8)
C1	0.0411 (11)	0.0380 (11)	0.0562 (13)	0.0045 (10)	0.0081 (10)	0.0102 (10)
C2	0.0521 (13)	0.0568 (14)	0.0572 (14)	0.0027 (12)	0.0138 (12)	0.0231 (12)
C3	0.0648 (17)	0.0809 (19)	0.0404 (12)	0.0116 (15)	0.0189 (12)	0.0099 (13)
N3	0.0405 (8)	0.0157 (6)	0.0376 (8)	−0.0018 (6)	0.0083 (7)	−0.0012 (6)
C17	0.090 (2)	0.0473 (13)	0.0379 (11)	0.0056 (14)	−0.0010 (12)	0.0081 (10)
C8	0.0402 (12)	0.0805 (19)	0.0558 (14)	0.0078 (13)	−0.0026 (11)	−0.0025 (13)
C5	0.0418 (11)	0.0420 (12)	0.0505 (12)	0.0027 (10)	0.0077 (10)	−0.0021 (9)
C4	0.0680 (16)	0.0596 (16)	0.0456 (12)	0.0113 (13)	0.0119 (11)	−0.0092 (12)
C13	0.0491 (12)	0.0486 (13)	0.0456 (12)	−0.0100 (10)	−0.0059 (9)	0.0022 (10)
C12	0.0523 (15)	0.0623 (17)	0.0751 (18)	−0.0195 (13)	−0.0145 (13)	0.0149 (14)

S—O3	1.4287 (18)	C15—H15B	0.9700
S—O2	1.4317 (16)	C7—C6	1.516 (3)
S—N3	1.6236 (16)	C7—H7A	0.9700
S—C17	1.744 (3)	C7—H7B	0.9700
P—O1	1.4794 (13)	C6—C5	1.384 (3)
P—N2	1.6285 (18)	C6—C1	1.390 (3)
P—N1	1.6326 (17)	C1—C2	1.387 (3)
P—N3	1.6714 (15)	C1—H1	0.9300
N2—C16	1.458 (3)	C2—C3	1.378 (4)
N2—C15	1.461 (3)	C2—H2	0.9300
N1—C7	1.465 (3)	C3—C4	1.369 (4)
N1—C8	1.467 (3)	C3—H3	0.9300
C16—H16A	0.9600	N3—H	0.8600
C16—H16B	0.9600	C17—H17A	0.9600
C16—H16C	0.9600	C17—H17B	0.9600
C11—C12	1.368 (5)	C17—H17C	0.9600
C11—C10	1.367 (5)	C8—H8A	0.9600
C11—H11	0.9300	C8—H8B	0.9600
C10—C9	1.392 (4)	C8—H8C	0.9600
C10—H10	0.9300	C5—C4	1.387 (3)
C9—C14	1.387 (3)	C5—H5	0.9300
C9—H9	0.9300	C4—H4	0.9300
C14—C13	1.378 (3)	C13—C12	1.387 (4)
C14—C15	1.507 (3)	C13—H13	0.9300
C15—H15A	0.9700	C12—H12	0.9300
O3—S—O2	118.53 (12)	C6—C7—H7A	108.8
O3—S—N3	109.61 (10)	N1—C7—H7B	108.8
O2—S—N3	106.39 (9)	C6—C7—H7B	108.8
O3—S—C17	107.61 (13)	H7A—C7—H7B	107.7
O2—S—C17	109.08 (12)	C5—C6—C1	119.2 (2)
N3—S—C17	104.79 (12)	C5—C6—C7	121.98 (19)
O1—P—N2	117.02 (9)	C1—C6—C7	118.82 (19)
O1—P—N1	110.51 (9)	C2—C1—C6	120.3 (2)
N2—P—N1	106.20 (9)	C2—C1—H1	119.8
O1—P—N3	108.94 (8)	C6—C1—H1	119.8
N2—P—N3	104.84 (9)	C3—C2—C1	120.0 (2)
N1—P—N3	108.98 (8)	C3—C2—H2	120.0
C16—N2—C15	115.69 (19)	C1—C2—H2	120.0
C16—N2—P	126.49 (17)	C4—C3—C2	119.8 (2)
C15—N2—P	117.76 (15)	C4—C3—H3	120.1
C7—N1—C8	115.7 (2)	C2—C3—H3	120.1
C7—N1—P	120.48 (14)	S—N3—P	125.05 (9)
C8—N1—P	118.83 (16)	S—N3—H	117.5
N2—C16—H16A	109.5	P—N3—H	117.5
N2—C16—H16B	109.5	S—C17—H17A	109.5
H16A—C16—H16B	109.5	S—C17—H17B	109.5
N2—C16—H16C	109.5	H17A—C17—H17B	109.5
H16A—C16—H16C	109.5	S—C17—H17C	109.5
H16B—C16—H16C	109.5	H17A—C17—H17C	109.5
C12—C11—C10	120.5 (3)	H17B—C17—H17C	109.5
C12—C11—H11	119.8	N1—C8—H8A	109.5
C10—C11—H11	119.8	N1—C8—H8B	109.5
C11—C10—C9	119.6 (3)	H8A—C8—H8B	109.5
C11—C10—H10	120.2	N1—C8—H8C	109.5
C9—C10—H10	120.2	H8A—C8—H8C	109.5
C14—C9—C10	120.6 (3)	H8B—C8—H8C	109.5
C14—C9—H9	119.7	C6—C5—C4	119.9 (2)
C10—C9—H9	119.7	C6—C5—H5	120.1
C13—C14—C9	118.5 (2)	C4—C5—H5	120.1
C13—C14—C15	122.87 (19)	C3—C4—C5	120.8 (2)
C9—C14—C15	118.6 (2)	C3—C4—H4	119.6
N2—C15—C14	115.23 (18)	C5—C4—H4	119.6
N2—C15—H15A	108.5	C14—C13—C12	120.8 (2)
C14—C15—H15A	108.5	C14—C13—H13	119.6
N2—C15—H15B	108.5	C12—C13—H13	119.6
C14—C15—H15B	108.5	C11—C12—C13	119.9 (3)
H15A—C15—H15B	107.5	C11—C12—H12	120.0
N1—C7—C6	113.73 (16)	C13—C12—H12	120.0
N1—C7—H7A	108.8
O1—P—N2—C16	114.6 (2)	P—N1—C7—C6	−138.44 (18)
N1—P—N2—C16	−121.5 (2)	N1—C7—C6—C5	24.7 (3)
N3—P—N2—C16	−6.2 (2)	N1—C7—C6—C1	−157.2 (2)
O1—P—N2—C15	−62.24 (18)	C5—C6—C1—C2	0.3 (3)
N1—P—N2—C15	61.66 (17)	C7—C6—C1—C2	−177.8 (2)
N3—P—N2—C15	176.96 (15)	C6—C1—C2—C3	−0.5 (4)
O1—P—N1—C7	175.63 (16)	C1—C2—C3—C4	0.3 (4)
N2—P—N1—C7	47.76 (19)	O3—S—N3—P	−41.70 (16)
N3—P—N1—C7	−64.70 (18)	O2—S—N3—P	−170.99 (13)
O1—P—N1—C8	−30.5 (2)	C17—S—N3—P	73.54 (16)
N2—P—N1—C8	−158.39 (18)	O1—P—N3—S	−25.84 (16)
N3—P—N1—C8	89.15 (19)	N2—P—N3—S	100.16 (13)
C12—C11—C10—C9	−0.9 (5)	N1—P—N3—S	−146.48 (13)
C11—C10—C9—C14	2.4 (5)	C1—C6—C5—C4	0.1 (4)
C10—C9—C14—C13	−1.7 (4)	C7—C6—C5—C4	178.2 (2)
C10—C9—C14—C15	177.4 (2)	C2—C3—C4—C5	0.2 (4)
C16—N2—C15—C14	−72.4 (3)	C6—C5—C4—C3	−0.4 (4)
P—N2—C15—C14	104.8 (2)	C9—C14—C13—C12	−0.3 (4)
C13—C14—C15—N2	−15.1 (3)	C15—C14—C13—C12	−179.4 (2)
C9—C14—C15—N2	165.9 (2)	C10—C11—C12—C13	−1.2 (5)
C8—N1—C7—C6	66.9 (3)	C14—C13—C12—C11	1.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H···O1i	0.86	1.91	2.7152 (19)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H⋯O1i	0.86	1.91	2.7152 (19)	155

Symmetry code: (i) .