N,N′-Dibenzyl-N,N′-dimethyl-N′′-(methyl­sulfon­yl)phospho­ric triamide

Pourayoubi, M.; Sadeghi Seraji, S.; Bruno, G.; Amiri Rudbari, H.

doi:10.1107/S1600536811015832

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1285

doi:10.1107/S1600536811015832

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N,N′-Dibenzyl-N,N′-dimethyl-N′′-(methylsulfonyl)phosphoric triamide

Mehrdad Pourayoubi,^a ^* Sepideh Sadeghi Seraji,^a Giuseppe Bruno ^b and Hadi Amiri Rudbari ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDipartimento di Chimica Inorganica, Vill. S. Agata, Salita Sperone 31, Università di Messina, 98166 Messina, Italy
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 23 March 2011; accepted 26 April 2011; online 7 May 2011)

In the title compound, C₁₇H₂₄N₃O₃PS, the P and the S atoms are each in a distorted tetrahedral environment and the N atoms display sp² 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 sulfonamide compound, see: Ibrahim et al. (2011 ) and references cited therein.

Experimental

Crystal data

C₁₇H₂₄N₃O₃PS
M_r = 381.42
Orthorhombic, P 2₁ 2₁ 2₁
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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.094
S = 1.08
4155 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1769 Friedel pairs
Flack parameter: 0.02 (7)

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) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

Structure determination of the title compound, CH₃S(O)₂NHP(O)[N(CH₃)(CH₂C₆H₅)]₂ (Fig. 1), was performed as a part of a project in our laboratory on the synthesis of new phosphoramidate compounds having a P(O)[N(CH₃)(CH₂C₆H₅)]₂ moiety (Pourayoubi et al., 2010).

The P═O and P—N bond lengths are comparable to those in similar phosphoramidates of the formula XP(O)[N(CH₃)(CH₂C₆H₅)]₂ [where X = Cl, C₆H₅C(O)NH, CCl₃C(O)NH] (Gholivand et al., 2005). The P—N1 and P—N2 bonds (with bond lengths of 1.6326 (17) Å and 1.6285 (18) Å) are shorter than the P—N3 bond (1.6714 (15) Å). The S═O bond lengths of 1.4317 (16) Å & 1.4287 (18) Å are standard for sulfonamide compounds (Ibrahim et al., 2011).

Each of the phosphorus and sulfur atoms has a distorted tetrahedral configuration. The surrounding bond angles are in the range of 104.84 (9)° to 117.02 (9)° around the P atom and 104.79 (12)° to 118.53 (12)° for the S atom. The average of surrounding angles around the tertiary nitrogen atom N2 (which is about 120°) shows that it is bonded in an essentially planar geometry; whereas, the environment of N1 is slightly deviated from planarity (average of bond angles is 118.3°). Furthermore, the S—N3—P angle is 125.05 (9)°. The dihedral angle between the mean planes of the benzene rings is 31.08 (8)°.

The phosphoryl group and the NH unit adopt the anti orientations with respect to each other. Crystal packing is stabilized by N—H···O hydrogen bonds, forming an extended chain parallel to the b axis (Fig. 2).

Related literature top

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 sulfonamide compound, see: Ibrahim et al. (2011) and references cited therein.

Experimental top

CH₃S(O)₂NHP(O)Cl₂ was synthesized from the reaction between phosphorus pentachloride (16.7 mmol) and methanesulfonamide (16.7 mmol) in dry CCl₄ at 353 K (3 h) and then treated with formic acid 85% (16.7 mmol) at ice bath temperature.

To a solution of CH₃S(O)₂NHP(O)Cl₂ (2.35 mmol) in dry chloroform (30 ml), a solution of N-methylbenzylamine (9.40 mmol) in the same solvent (10 ml) was added at ice bath temperature. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from CH₃CN/CHCl₃ at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. An ORTEP-style plot of title compound with labeling. Ellipsoids are given at the 50% probability level.
	Fig. 2. Partial packing view showing the formation of the chain through N—H···O hydrogen bonds which are shown as dotted lines. H atoms not involved in hydrogen bondings have been omitted for the sake of clarity. [Symmetry code: (i) -x, y + 1/2, -z + 1/2]

N,N'-Dibenzyl-N,N'-dimethyl- N''-(methylsulfonyl)phosphoric triamide top

Crystal data top

C₁₇H₂₄N₃O₃PS	F(000) = 808
M_r = 381.42	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0564P)² + 0.4498P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
4155 reflections	Δρ_max = 0.30 e Å⁻³
226 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1769 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (7)

Crystal data top

C₁₇H₂₄N₃O₃PS	V = 1915.29 (16) Å³
M_r = 381.42	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.5343 (4) Å	µ = 0.27 mm⁻¹
b = 10.1800 (5) Å	T = 296 K
c = 22.0455 (10) Å	0.47 × 0.38 × 0.30 mm

Data collection top

Bruker APEXII CCD diffractometer	4155 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3937 reflections with I > 2σ(I)
T_min = 0.700, T_max = 0.746	R_int = 0.060
65627 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.094	Δρ_max = 0.30 e Å⁻³
S = 1.08	Δρ_min = −0.22 e Å⁻³
4155 reflections	Absolute structure: Flack (1983), 1769 Friedel pairs
226 parameters	Absolute structure parameter: 0.02 (7)
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₄N₃O₃PS
M_r	381.42
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.5343 (4), 10.1800 (5), 22.0455 (10)
V (Å³)	1915.29 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.47 × 0.38 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.700, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	65627, 4155, 3937
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.094, 1.08
No. of reflections	4155
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22
Absolute structure	Flack (1983), 1769 Friedel pairs
Absolute structure parameter	0.02 (7)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), SHELXTL (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

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) −x, y+1/2, −z+1/2.

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gholivand, K., Pourayoubi, M., Shariatinia, Z. & Mostaanzadeh, H. (2005). Polyhedron, 24, 655–662. Web of Science CSD CrossRef CAS Google Scholar
Ibrahim, S., Tahir, M. N., Iqbal, N., Shahwar, D. & Raza, M. A. (2011). Acta Cryst. E67, o298. Web of Science CSD CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pourayoubi, M., Tarahhomi, A., Rheingold, A. L. & Golen, J. A. (2010). Acta Cryst. E66, o2524. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2004). SADABS. Uinversity of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar