N,N'-Dicyclo-pentyl-N'',N''-dimethyl-phospho-ric triamide.

The P atom in the title mol-ecule, C(12)H(26)N(3)OP, has a distorted tetra-hedral configuration: its bond angles lie in the range 101.1 (2)-119.1 (2)°. The P-N bonds to the two cyclo-pentyl-amido moieties are significantly different [1.619 (4) and 1.643 (4) Å], with the shorter bond related to an anti orientation of the lone electron pair of the corresponding N atom relative to the P=O bond. The O atom of the P=O group acts as a double hydrogen-bond acceptor and is involved in two different inter-molecular N-H⋯O(P) hydrogen bonds, building R(2) (2)(8) rings that are further linked into chains along [001].

Related literature

For background to phospho­ric triamide compounds, see: Pourayoubi & Tarahhomi et al. (2011 ▶). For applications of phospho­ric triamides as oxygen-donor ligands, see: Pourayoubi & Golen et al. (2011 ▶). For bond lengths and angles in compounds having a [(N)P(O)(N)2] skeleton, see: Sabbaghi et al. (2011 ▶). For double hydrogen-bond acceptors, see: Steiner (2002 ▶).

Experimental

Crystal data

C12H26N3OP

M = 259.33

Orthorhombic,

a = 10.962 (5) Å

b = 16.663 (5) Å

c = 8.079 (5) Å

V = 1475.7 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 291 K

0.35 × 0.11 × 0.05 mm

Data collection

Stoe IPDS 2T Image Plate diffractometer

Absorption correction: multi-scan [MULABS (Blessing, 1995 ▶) and PLATON (Spek, 2009 ▶)] T min = 0.961, T max = 1.000

7303 measured reflections

2573 independent reflections

1482 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.108

S = 0.88

2573 reflections

151 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.23 e Å−3

Absolute structure: Flack (1983 ▶), 1093 Friedel pairs

Flack parameter: −0.20 (18)

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PLATON (Spek, 2009 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048549/ld2034sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048549/ld2034Isup2.hkl

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

C12H26N3OP	F(000) = 568
Mr = 259.33	Dx = 1.167 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2c -2ac	Cell parameters from 2536 reflections
a = 10.962 (5) Å	θ = 2.0–27.5°
b = 16.663 (5) Å	µ = 0.18 mm−1
c = 8.079 (5) Å	T = 291 K
V = 1475.7 (12) Å3	Needle, colourless
Z = 4	0.35 × 0.11 × 0.05 mm

Stoe IPDS 2T Image Plate diffractometer	2573 independent reflections
Radiation source: fine-focus sealed tube	1482 reflections with I > 2σ(I)
graphite	Rint = 0.095
Detector resolution: 0.15 pixels mm-1	θmax = 25.5°, θmin = 2.2°
ω scans	h = −11→13
Absorption correction: multi-scan [MULABS (Blessing, 1995) and PLATON (Spek, 2009)]	k = −20→20
Tmin = 0.961, Tmax = 1.000	l = −8→9
7303 measured reflections

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)] = 0.056	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0401P)2] where P = (Fo2 + 2Fc2)/3
S = 0.88	(Δ/σ)max < 0.001
2573 reflections	Δρmax = 0.16 e Å−3
151 parameters	Δρmin = −0.23 e Å−3
1 restraint	Absolute structure: Flack (1983), 1093 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.20 (18)

Experimental. IR (KBr, cm-1): 3290, 3151, 2955, 2866, 2835, 2794, 1459, 1291, 1197, 1159, 1107, 1090, 1030, 993, 932, 889, 762, 703, 555, 496, 464.

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	0.83134 (10)	1.79029 (6)	0.70933 (17)	0.0402 (3)
O1	0.6995 (2)	1.78019 (14)	0.7413 (4)	0.0476 (9)
N1	0.8963 (4)	1.73464 (16)	0.5707 (5)	0.0418 (10)
H1	0.8771	1.7422	0.4700	0.050*
N2	0.9056 (3)	1.77094 (19)	0.8814 (5)	0.0452 (10)
H2	0.8616	1.7816	0.9651	0.054*
N3	0.8558 (4)	1.8809 (2)	0.6328 (4)	0.0545 (12)
C1	0.9062 (4)	1.6462 (2)	0.5936 (6)	0.0458 (12)
H1A	0.9222	1.6352	0.7108	0.055*
C2	1.0064 (5)	1.6094 (3)	0.4926 (9)	0.088 (2)
H2A	1.0841	1.6147	0.5489	0.106*
H2B	1.0121	1.6354	0.3854	0.106*
C3	0.9725 (6)	1.5223 (3)	0.4730 (10)	0.100 (2)
H3A	0.9884	1.5046	0.3606	0.121*
H3B	1.0201	1.4894	0.5481	0.121*
C4	0.8410 (6)	1.5149 (3)	0.5115 (10)	0.096 (2)
H4A	0.8291	1.4821	0.6093	0.115*
H4B	0.7979	1.4903	0.4197	0.115*
C5	0.7943 (5)	1.5994 (2)	0.5411 (7)	0.0678 (17)
H5A	0.7594	1.6216	0.4408	0.081*
H5B	0.7328	1.5999	0.6275	0.081*
C6	1.0370 (4)	1.7749 (2)	0.9067 (6)	0.0480 (12)
H6A	1.0773	1.7747	0.7984	0.058*
C7	1.0855 (5)	1.7061 (3)	1.0069 (7)	0.0700 (15)
H7A	1.0208	1.6825	1.0729	0.084*
H7B	1.1188	1.6650	0.9348	0.084*
C8	1.1810 (7)	1.7386 (4)	1.1141 (11)	0.139 (2)
H8A	1.1771	1.7136	1.2224	0.167*
H8B	1.2607	1.7279	1.0669	0.167*
C9	1.1626 (7)	1.8212 (4)	1.1282 (9)	0.139 (2)
H9A	1.2401	1.8488	1.1166	0.167*
H9B	1.1302	1.8334	1.2371	0.167*
C10	1.0791 (5)	1.8495 (2)	1.0034 (8)	0.0702 (17)
H10A	1.1195	1.8872	0.9301	0.084*
H10B	1.0099	1.8761	1.0544	0.084*
C11	0.9700 (5)	1.9066 (3)	0.5626 (8)	0.0808 (19)
H11A	0.9552	1.9478	0.4820	0.121*
H11B	1.0094	1.8619	0.5103	0.121*
H11C	1.0215	1.9274	0.6487	0.121*
C12	0.7793 (6)	1.9460 (2)	0.6916 (10)	0.093 (2)
H12A	0.7768	1.9877	0.6098	0.139*
H12B	0.8122	1.9669	0.7929	0.139*
H12C	0.6982	1.9263	0.7109	0.139*

	U11	U22	U33	U12	U13	U23
P1	0.0424 (6)	0.0398 (4)	0.0385 (6)	−0.0033 (5)	−0.0014 (9)	0.0013 (7)
O1	0.0381 (18)	0.0585 (16)	0.046 (3)	−0.0026 (13)	−0.0026 (18)	0.0068 (16)
N1	0.054 (3)	0.0364 (17)	0.035 (2)	−0.0031 (17)	0.000 (2)	0.0055 (17)
N2	0.039 (3)	0.057 (2)	0.039 (2)	−0.0055 (19)	0.006 (2)	−0.0082 (19)
N3	0.060 (3)	0.0419 (19)	0.061 (3)	−0.0004 (19)	0.010 (2)	0.0020 (16)
C1	0.058 (3)	0.042 (2)	0.037 (3)	0.010 (2)	−0.002 (3)	0.001 (2)
C2	0.073 (4)	0.060 (3)	0.131 (6)	0.006 (3)	0.038 (5)	0.004 (4)
C3	0.112 (6)	0.067 (4)	0.122 (6)	0.022 (3)	0.016 (6)	−0.035 (4)
C4	0.098 (5)	0.051 (3)	0.140 (7)	0.007 (3)	−0.010 (6)	−0.012 (3)
C5	0.057 (4)	0.052 (3)	0.095 (5)	−0.002 (2)	−0.006 (3)	−0.002 (3)
C6	0.038 (3)	0.050 (3)	0.056 (3)	0.000 (2)	−0.004 (3)	0.001 (2)
C7	0.068 (4)	0.058 (3)	0.085 (4)	0.005 (3)	−0.017 (4)	0.007 (3)
C8	0.158 (6)	0.107 (3)	0.154 (5)	0.012 (4)	−0.095 (5)	−0.004 (3)
C9	0.158 (6)	0.107 (3)	0.154 (5)	0.012 (4)	−0.095 (5)	−0.004 (3)
C10	0.064 (4)	0.047 (3)	0.099 (5)	−0.007 (2)	−0.017 (4)	−0.016 (3)
C11	0.086 (5)	0.059 (3)	0.097 (5)	−0.016 (3)	0.005 (4)	0.025 (3)
C12	0.129 (5)	0.052 (3)	0.098 (6)	0.015 (3)	0.034 (6)	−0.001 (4)

P1—O1	1.478 (3)	C5—H5A	0.9700
P1—N1	1.619 (4)	C5—H5B	0.9700
P1—N2	1.643 (4)	C6—C7	1.500 (6)
P1—N3	1.653 (4)	C6—C10	1.539 (6)
N1—C1	1.489 (4)	C6—H6A	0.9800
N1—H1	0.8499	C7—C8	1.463 (8)
N2—C6	1.456 (5)	C7—H7A	0.9700
N2—H2	0.8489	C7—H7B	0.9700
N3—C11	1.440 (6)	C8—C9	1.395 (8)
N3—C12	1.451 (6)	C8—H8A	0.9700
C1—C2	1.499 (7)	C8—H8B	0.9700
C1—C5	1.515 (6)	C9—C10	1.441 (7)
C1—H1A	0.9800	C9—H9A	0.9700
C2—C3	1.508 (6)	C9—H9B	0.9700
C2—H2A	0.9700	C10—H10A	0.9700
C2—H2B	0.9700	C10—H10B	0.9700
C3—C4	1.480 (8)	C11—H11A	0.9600
C3—H3A	0.9700	C11—H11B	0.9600
C3—H3B	0.9700	C11—H11C	0.9600
C4—C5	1.516 (6)	C12—H12A	0.9600
C4—H4A	0.9700	C12—H12B	0.9600
C4—H4B	0.9700	C12—H12C	0.9600
O1—P1—N1	119.06 (19)	H5A—C5—H5B	108.9
O1—P1—N2	108.3 (2)	N2—C6—C7	113.0 (4)
N1—P1—N2	104.78 (19)	N2—C6—C10	113.9 (4)
O1—P1—N3	109.13 (18)	C7—C6—C10	103.7 (4)
N1—P1—N3	101.13 (19)	N2—C6—H6A	108.7
N2—P1—N3	114.55 (18)	C7—C6—H6A	108.7
C1—N1—P1	120.9 (3)	C10—C6—H6A	108.7
C1—N1—H1	106.5	C8—C7—C6	106.9 (4)
P1—N1—H1	117.9	C8—C7—H7A	110.3
C6—N2—P1	126.8 (3)	C6—C7—H7A	110.3
C6—N2—H2	116.2	C8—C7—H7B	110.3
P1—N2—H2	110.6	C6—C7—H7B	110.3
C11—N3—C12	114.1 (4)	H7A—C7—H7B	108.6
C11—N3—P1	124.1 (3)	C9—C8—C7	108.1 (6)
C12—N3—P1	117.8 (3)	C9—C8—H8A	110.1
N1—C1—C2	113.0 (4)	C7—C8—H8A	110.1
N1—C1—C5	114.6 (4)	C9—C8—H8B	110.1
C2—C1—C5	103.3 (4)	C7—C8—H8B	110.1
N1—C1—H1A	108.6	H8A—C8—H8B	108.4
C2—C1—H1A	108.6	C8—C9—C10	110.9 (6)
C5—C1—H1A	108.6	C8—C9—H9A	109.5
C1—C2—C3	105.7 (4)	C10—C9—H9A	109.5
C1—C2—H2A	110.6	C8—C9—H9B	109.5
C3—C2—H2A	110.6	C10—C9—H9B	109.5
C1—C2—H2B	110.6	H9A—C9—H9B	108.0
C3—C2—H2B	110.6	C9—C10—C6	106.4 (4)
H2A—C2—H2B	108.7	C9—C10—H10A	110.5
C4—C3—C2	107.3 (4)	C6—C10—H10A	110.5
C4—C3—H3A	110.3	C9—C10—H10B	110.5
C2—C3—H3A	110.3	C6—C10—H10B	110.5
C4—C3—H3B	110.3	H10A—C10—H10B	108.6
C2—C3—H3B	110.3	N3—C11—H11A	109.5
H3A—C3—H3B	108.5	N3—C11—H11B	109.5
C3—C4—C5	106.6 (4)	H11A—C11—H11B	109.5
C3—C4—H4A	110.4	N3—C11—H11C	109.5
C5—C4—H4A	110.4	H11A—C11—H11C	109.5
C3—C4—H4B	110.4	H11B—C11—H11C	109.5
C5—C4—H4B	110.4	N3—C12—H12A	109.5
H4A—C4—H4B	108.6	N3—C12—H12B	109.5
C1—C5—C4	104.4 (4)	H12A—C12—H12B	109.5
C1—C5—H5A	110.9	N3—C12—H12C	109.5
C4—C5—H5A	110.9	H12A—C12—H12C	109.5
C1—C5—H5B	110.9	H12B—C12—H12C	109.5
C4—C5—H5B	110.9
O1—P1—N1—C1	−65.4 (4)	C5—C1—C2—C3	−32.8 (6)
N2—P1—N1—C1	55.8 (4)	C1—C2—C3—C4	17.9 (8)
N3—P1—N1—C1	175.1 (3)	C2—C3—C4—C5	4.3 (8)
O1—P1—N2—C6	−178.9 (3)	N1—C1—C5—C4	158.6 (5)
N1—P1—N2—C6	53.0 (4)	C2—C1—C5—C4	35.2 (6)
N3—P1—N2—C6	−56.8 (4)	C3—C4—C5—C1	−24.6 (7)
O1—P1—N3—C11	−169.5 (4)	P1—N2—C6—C7	−138.0 (4)
N1—P1—N3—C11	−43.2 (4)	P1—N2—C6—C10	104.0 (5)
N2—P1—N3—C11	68.9 (4)	N2—C6—C7—C8	−142.0 (5)
O1—P1—N3—C12	34.3 (5)	C10—C6—C7—C8	−18.2 (6)
N1—P1—N3—C12	160.6 (4)	C6—C7—C8—C9	20.8 (8)
N2—P1—N3—C12	−87.3 (4)	C7—C8—C9—C10	−14.8 (9)
P1—N1—C1—C2	−158.0 (4)	C8—C9—C10—C6	2.8 (8)
P1—N1—C1—C5	84.1 (5)	N2—C6—C10—C9	132.9 (5)
N1—C1—C2—C3	−157.2 (5)	C7—C6—C10—C9	9.7 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.85	2.13	2.960 (5)	167
N2—H2···O1ii	0.85	2.33	3.131 (5)	158
C11—H11B···N1	0.96	2.50	2.978 (6)	110
C12—H12C···O1	0.96	2.45	2.926 (5)	111

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.85	2.13	2.960 (5)	167
N2—H2⋯O1ii	0.85	2.33	3.131 (5)	158

Symmetry codes: (i) ; (ii) .