N,N′-Dicyclo­pentyl-N′′,N′′-dimethyl­phospho­ric triamide

Raissi Shabari, A.; Pourayoubi, M.; Ghoreishi, F.; Vahdani, B.

doi:10.1107/S1600536811048549

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3401

https://doi.org/10.1107/S1600536811048549

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N,N′-Dicyclopentyl-N′′,N′′-dimethylphosphoric triamide

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi,^b Farnaz Ghoreishi ^a and Banafsheh Vahdani ^a

^aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, and ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran
^*Correspondence e-mail: a.raissi_shabari@yahoo.com

(Received 27 October 2011; accepted 15 November 2011; online 23 November 2011)

The P atom in the title molecule, C₁₂H₂₆N₃OP, has a distorted tetrahedral configuration: its bond angles lie in the range 101.1 (2)–119.1 (2)°. The P—N bonds to the two cyclopentylamido 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 intermolecular N—H⋯O(P) hydrogen bonds, building R₂²(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_r = 259.33
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.056
wR(F²) = 0.108
S = 0.88
2573 reflections
151 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ), 1093 Friedel pairs
Flack parameter: −0.20 (18)

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) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811048549/ld2034sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811048549/ld2034Isup2.hkl

checkCIF report

Comment top

The structure determination of the title molecule was done as part of a project on the synthesis of new phosphoric triamide compounds (Pourayoubi & Tarahhomi et al., 2011) and their application as oxygen donor ligands (Pourayoubi & Golen et al., 2011).

The P═O and P—N bond lengths and the C—N—P bond angles match those found for the other compounds having a [(N)P(O)(N)₂] skeleton (Sabbaghi et al., 2011).

The tetrahedral configuration of phosphorus atom (Fig. 1) is significantly distorted as it has also been noted for other phosphoric triamides: the bond angles at the P atom vary in the range from 101.1 (2) [N1—P1—N3] to 119.1 (2)° [O1—P1—N1].

The O atom of the P═O group acts as a double hydrogen-bond acceptor (Steiner, 2002); so, in the crystal structure, each molecule is hydrogen-bonded to two adjacent molecules by forming the [N—H]₂···O(P) grouping within a 1-D hydrogen-bonded arrangement parallel to the c axis (Fig. 2, Table 1).

Related literature top

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 top

Synthesis of ((CH₃)₂N)P(O)Cl₂: [(CH₃)₂NH₂]Cl (0.184 mol) and P(O)Cl₃ (0.552 mol) were refluxed for 8 h and afterwards the excess of P(O)Cl₃ was removed in vacuum.

Synthesis of title compound: a solution of cyclopentylamine (14.8 mmol) in CH₃CN (25 ml) was added to a solution of ((CH₃)₂N)P(O)Cl₂ (3.7 mmol) in CH₃CN (15 ml) at 273 K. After stirring for 4 h, the solvent was removed and the product was washed with deionized water and recrystallized from CH₃CN at room temperature.

Structure description top

The P═O and P—N bond lengths and the C—N—P bond angles match those found for the other compounds having a [(N)P(O)(N)₂] skeleton (Sabbaghi et al., 2011).

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level.
	Fig. 2. A view of the crystal packing showing the formation of 1-D arrangement through N—H···O hydrogen bonds (shown as dashed lines). Carbon bound H atoms have been omitted for clarity.

N,N'-Dicyclopentyl-N'',N''-dimethylphosphoric triamide top

Crystal data top

C₁₂H₂₆N₃OP	F(000) = 568
M_r = 259.33	D_x = 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

Data collection top

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

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)] = 0.056	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0401P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max < 0.001
2573 reflections	Δρ_max = 0.16 e Å⁻³
151 parameters	Δρ_min = −0.23 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1093 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.20 (18)

Crystal data top

C₁₂H₂₆N₃OP	V = 1475.7 (12) Å³
M_r = 259.33	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 10.962 (5) Å	µ = 0.18 mm⁻¹
b = 16.663 (5) Å	T = 291 K
c = 8.079 (5) Å	0.35 × 0.11 × 0.05 mm

Data collection top

Stoe IPDS 2T Image Plate diffractometer	2573 independent reflections
Absorption correction: multi-scan [MULABS (Blessing, 1995) and PLATON (Spek, 2009)]	1482 reflections with I > 2σ(I)
T_min = 0.961, T_max = 1.000	R_int = 0.095
7303 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	H-atom parameters constrained
wR(F²) = 0.108	Δρ_max = 0.16 e Å⁻³
S = 0.88	Δρ_min = −0.23 e Å⁻³
2573 reflections	Absolute structure: Flack (1983), 1093 Friedel pairs
151 parameters	Absolute structure parameter: −0.20 (18)
1 restraint

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+3/2, y, z−1/2; (ii) −x+3/2, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₂₆N₃OP
M_r	259.33
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	291
a, b, c (Å)	10.962 (5), 16.663 (5), 8.079 (5)
V (Å³)	1475.7 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.35 × 0.11 × 0.05

Data collection
Diffractometer	Stoe IPDS 2T Image Plate
Absorption correction	Multi-scan [MULABS (Blessing, 1995) and PLATON (Spek, 2009)]
T_min, T_max	0.961, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7303, 2573, 1482
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.108, 0.88
No. of reflections	2573
No. of parameters	151
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23
Absolute structure	Flack (1983), 1093 Friedel pairs
Absolute structure parameter	−0.20 (18)

Computer programs: X-AREA (Stoe & Cie, 2009), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y, z−1/2; (ii) −x+3/2, y, z+1/2.

Acknowledgements

Support of this investigation by the North Tehran Branch, Islamic Azad University, is gratefully acknowledged.

References

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