Diphenyl [(S)-1-phenylpropanamido]­phosphate

Sabbaghi, F.; Pourayoubi, M.; Negari, M.; Nečas, M.

doi:10.1107/S1600536811034507

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2512

doi:10.1107/S1600536811034507

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Diphenyl [(S)-1-phenylpropanamido]phosphate

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi,^b Monireh Negari ^b and Marek Nečas ^c

^aDepartment of Chemistry, Zanjan Branch, Islamic Azad University, PO Box 49195-467, Zanjan, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and ^cDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 12 August 2011; accepted 22 August 2011; online 27 August 2011)

The title compound, C₂₁H₂₂NO₃P, was synthesized from the reaction of (C₆H₅O)₂P(O)(Cl) and S-1-phenylpropylamine (1:2 mole ratio) at 273 K, followed by removal of the S-1-phenylpropylamine hydrochloride by-product by dissolving in H₂O. The P atom is located in a distorted tetrahedral environment. The bond angles at the P atom vary from 99.51 (12) to 116.68 (12)°. The sp² character of the N atom is reflected by the C—N—P angle [120.9 (2)°]. The P=O group and the N—H unit adopt an anti orientation with respect to one another. In the crystal, adjacent molecules are linked via N—H⋯O(P) hydrogen bonds into a one-dimensional arrangement running parallel to the a axis.

Related literature

For background literature on phosphoramidates having a C(=O)NHP(=O) skeleton, and the hydrogen-bond patterns and strengths, see: Toghraee et al. (2011 ); Pourayoubi et al. (2011 ). For a related phosphoramidate with a P(=O)(O)₂(N) skeleton, and its bond lengths and angles, see: Pourayoubi et al. (2010 ).

Experimental

Crystal data

C₂₁H₂₂NO₃P
M_r = 367.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4853 (3) Å
b = 8.1450 (11) Å
c = 41.162 (4) Å
V = 1839.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.40 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.981, T_max = 1.000
4914 measured reflections
3000 independent reflections
2404 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.089
S = 1.07
3000 reflections
239 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.42 e Å⁻³
Absolute structure: Flack (1983 ), 1052 Friedel pairs
Flack parameter: −0.09 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.84 (1)	2.25 (1)	3.077 (3)	167 (3)
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; 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: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536811034507/dn2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811034507/dn2713Isup2.hkl

checkCIF report

Comment top

In recently published papers concerning phosphoramidate compounds having a C(═O)NHP(═O)(N)₂ skeleton, the hydrogen bonds pattern (Toghraee et al., 2011) and strengths (Pourayoubi et al., 2011) were analyzed. In our continuing interest, we collected the structural data related to a new compound with a P(═O)(O)₂(N) skeleton belonging to the phosphoramide family.

The molecular structure of the title compound is given in Fig. 1. The P═O, P—O and P—N bond lengths and the C—N—P and C—O—P angles are standard for this category of phosphoramidate compounds (Pourayoubi et al., 2010).

In the crystal structure, molecules are linked via N—H···O(P) hydrogen bonds into extended chains running parallel to the a axis (Table 1, Fig. 2).

Related literature top

For background literature on phosphoramidates having a C(═O)NHP(═O) skeleton, and the hydrogen-bond patterns and strengths, see: Toghraee et al. (2011); Pourayoubi et al. (2011). For a related phosphoramidate with a P(═O)(O)₂(N) skeleton, and its bond lengths and angles, see: Pourayoubi et al. (2010).

Experimental top

To a solution of (C₆H₅O)₂P(O)Cl in chloroform, a solution of S-1-phenylpropylamine (1:2 mole ratio) in chloroform was added at 273 K. After 4 h of stirring, the solvent was removed and the obtained solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in CHCl₃/n-C₇H₁₆ after slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. An ORTEP style plot and atom labeling scheme for the title compound. Displacement ellipsoids are given at 50% probability level and H atoms are drawn as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal packing of the title compound with the hydrogen bonds shown as dotted lines (the C—H hydrogen atoms are omitted for clarity).

Diphenyl [(S)-1-phenylpropanamido]phosphate top

Crystal data top

C₂₁H₂₂NO₃P	F(000) = 776
M_r = 367.37	D_x = 1.327 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1550 reflections
a = 5.4853 (3) Å	θ = 3.2–27.6°
b = 8.1450 (11) Å	µ = 0.17 mm⁻¹
c = 41.162 (4) Å	T = 120 K
V = 1839.0 (3) Å³	Plate, colorless
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	3000 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2404 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ω scan	h = −5→6
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −9→5
T_min = 0.981, T_max = 1.000	l = −48→48
4914 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)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0325P)² + 0.0316P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
3000 reflections	Δρ_max = 0.41 e Å⁻³
239 parameters	Δρ_min = −0.42 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1052 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (14)

Crystal data top

C₂₁H₂₂NO₃P	V = 1839.0 (3) Å³
M_r = 367.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.4853 (3) Å	µ = 0.17 mm⁻¹
b = 8.1450 (11) Å	T = 120 K
c = 41.162 (4) Å	0.40 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector	3000 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2404 reflections with I > 2σ(I)
T_min = 0.981, T_max = 1.000	R_int = 0.029
4914 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.089	Δρ_max = 0.41 e Å⁻³
S = 1.07	Δρ_min = −0.42 e Å⁻³
3000 reflections	Absolute structure: Flack (1983), 1052 Friedel pairs
239 parameters	Absolute structure parameter: −0.09 (14)
1 restraint

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	1.02848 (15)	0.21930 (11)	0.13952 (2)	0.0144 (2)
O1	1.0319 (4)	0.2594 (3)	0.10191 (4)	0.0190 (6)
O2	0.9231 (4)	0.3876 (2)	0.15288 (5)	0.0159 (5)
O3	1.2652 (4)	0.1671 (2)	0.15233 (5)	0.0168 (6)
N1	0.8109 (5)	0.0886 (3)	0.14460 (7)	0.0122 (6)
H1	0.664 (2)	0.118 (3)	0.1438 (7)	0.018*
C1	1.2275 (6)	0.3148 (4)	0.08300 (8)	0.0138 (8)
C2	1.4066 (6)	0.4158 (4)	0.09534 (8)	0.0175 (8)
H2A	1.4062	0.4477	0.1175	0.021*
C3	1.5882 (6)	0.4694 (4)	0.07423 (8)	0.0193 (9)
H3B	1.7151	0.5378	0.0822	0.023*
C4	1.5863 (7)	0.4244 (4)	0.04181 (9)	0.0237 (9)
H4A	1.7092	0.4635	0.0275	0.028*
C5	1.4054 (6)	0.3227 (4)	0.03045 (8)	0.0239 (9)
H5A	1.4044	0.2909	0.0082	0.029*
C6	1.2250 (6)	0.2665 (4)	0.05106 (7)	0.0186 (8)
H6A	1.1010	0.1954	0.0432	0.022*
C7	0.8931 (6)	0.4166 (4)	0.18657 (8)	0.0147 (8)
C8	1.0704 (7)	0.5046 (4)	0.20239 (8)	0.0232 (9)
H8A	1.2141	0.5378	0.1913	0.028*
C9	1.0358 (7)	0.5446 (4)	0.23511 (8)	0.0270 (9)
H9A	1.1575	0.6045	0.2465	0.032*
C10	0.8268 (7)	0.4975 (4)	0.25076 (9)	0.0277 (10)
H10A	0.8030	0.5250	0.2730	0.033*
C11	0.6510 (7)	0.4101 (4)	0.23415 (8)	0.0220 (9)
H11A	0.5062	0.3777	0.2451	0.026*
C12	0.6827 (6)	0.3689 (4)	0.20180 (8)	0.0170 (8)
H12A	0.5611	0.3090	0.1904	0.020*
C13	0.6168 (7)	−0.1630 (4)	0.18811 (7)	0.0273 (10)
H13A	0.4918	−0.2374	0.1966	0.041*
H13B	0.5715	−0.0493	0.1930	0.041*
H13C	0.7740	−0.1882	0.1983	0.041*
C14	0.6370 (6)	−0.1851 (4)	0.15156 (7)	0.0213 (9)
H14A	0.4814	−0.1515	0.1413	0.026*
H14B	0.6628	−0.3028	0.1467	0.026*
C15	0.8451 (6)	−0.0856 (4)	0.13654 (7)	0.0130 (7)
H15A	1.0005	−0.1226	0.1469	0.016*
C16	0.8667 (6)	−0.1162 (4)	0.10011 (8)	0.0131 (8)
C17	1.0577 (6)	−0.2086 (4)	0.08788 (7)	0.0175 (8)
H17A	1.1767	−0.2512	0.1024	0.021*
C18	1.0790 (6)	−0.2405 (4)	0.05478 (8)	0.0211 (9)
H18A	1.2099	−0.3055	0.0468	0.025*
C19	0.9076 (6)	−0.1766 (4)	0.03360 (8)	0.0213 (9)
H19A	0.9221	−0.1965	0.0109	0.026*
C20	0.7162 (7)	−0.0845 (4)	0.04518 (8)	0.0211 (9)
H20A	0.5981	−0.0413	0.0306	0.025*
C21	0.6966 (6)	−0.0549 (4)	0.07836 (8)	0.0178 (9)
H21A	0.5640	0.0086	0.0863	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0134 (4)	0.0160 (4)	0.0139 (5)	−0.0003 (4)	−0.0006 (4)	−0.0004 (4)
O1	0.0146 (12)	0.0300 (15)	0.0122 (11)	−0.0012 (13)	0.0002 (10)	0.0020 (10)
O2	0.0200 (13)	0.0115 (12)	0.0163 (12)	0.0000 (11)	−0.0005 (11)	−0.0006 (10)
O3	0.0136 (12)	0.0178 (13)	0.0191 (13)	−0.0002 (11)	−0.0008 (10)	−0.0001 (11)
N1	0.0132 (14)	0.0114 (15)	0.0119 (16)	0.0030 (13)	−0.0001 (14)	−0.0015 (13)
C1	0.0098 (18)	0.013 (2)	0.018 (2)	0.0016 (16)	0.0051 (14)	0.0038 (16)
C2	0.0175 (19)	0.0173 (18)	0.018 (2)	0.0038 (17)	0.0013 (16)	−0.0023 (16)
C3	0.0152 (19)	0.0126 (19)	0.030 (2)	−0.0028 (17)	−0.0017 (17)	0.0017 (17)
C4	0.020 (2)	0.022 (2)	0.029 (2)	0.0019 (18)	0.0120 (18)	0.0046 (19)
C5	0.028 (2)	0.031 (2)	0.0119 (19)	0.0009 (19)	0.0064 (16)	−0.0006 (17)
C6	0.0222 (19)	0.018 (2)	0.0157 (19)	−0.0053 (18)	−0.0017 (16)	0.0002 (16)
C7	0.0164 (19)	0.0115 (18)	0.0162 (19)	0.0029 (17)	−0.0031 (16)	−0.0003 (16)
C8	0.019 (2)	0.0183 (19)	0.032 (2)	−0.0011 (19)	0.0001 (19)	−0.0022 (17)
C9	0.027 (2)	0.025 (2)	0.029 (2)	0.000 (2)	−0.009 (2)	−0.0110 (18)
C10	0.036 (3)	0.030 (2)	0.017 (2)	0.010 (2)	−0.007 (2)	−0.0079 (19)
C11	0.024 (2)	0.027 (2)	0.015 (2)	0.003 (2)	0.0002 (17)	0.0016 (18)
C12	0.0167 (19)	0.016 (2)	0.019 (2)	−0.0012 (17)	−0.0067 (16)	−0.0012 (16)
C13	0.037 (2)	0.025 (2)	0.020 (2)	−0.0053 (19)	0.0051 (18)	0.0021 (18)
C14	0.028 (2)	0.0157 (19)	0.020 (2)	−0.0020 (17)	−0.0016 (16)	−0.0034 (17)
C15	0.0115 (16)	0.0149 (18)	0.0128 (18)	0.0017 (15)	−0.0032 (16)	0.0010 (17)
C16	0.0141 (18)	0.0083 (18)	0.017 (2)	−0.0031 (16)	−0.0005 (15)	−0.0012 (15)
C17	0.0180 (18)	0.0196 (18)	0.0148 (18)	−0.0021 (19)	−0.0024 (15)	−0.0027 (17)
C18	0.019 (2)	0.019 (2)	0.025 (2)	−0.0018 (18)	0.0042 (16)	−0.0069 (17)
C19	0.033 (2)	0.021 (2)	0.0102 (18)	−0.0100 (18)	0.0022 (16)	−0.0018 (16)
C20	0.029 (2)	0.020 (2)	0.014 (2)	−0.0004 (19)	−0.0041 (18)	0.0012 (17)
C21	0.021 (2)	0.016 (2)	0.016 (2)	0.0027 (17)	−0.0030 (17)	−0.0042 (16)

Geometric parameters (Å, º) top

P1—O3	1.465 (2)	C10—C11	1.380 (5)
P1—O1	1.582 (2)	C10—H10A	0.9500
P1—O2	1.586 (2)	C11—C12	1.384 (4)
P1—N1	1.613 (3)	C11—H11A	0.9500
O1—C1	1.400 (3)	C12—H12A	0.9500
O2—C7	1.417 (4)	C13—C14	1.519 (4)
N1—C15	1.469 (4)	C13—H13A	0.9800
N1—H1	0.838 (10)	C13—H13B	0.9800
C1—C6	1.372 (4)	C13—H13C	0.9800
C1—C2	1.378 (4)	C14—C15	1.530 (4)
C2—C3	1.392 (4)	C14—H14A	0.9900
C2—H2A	0.9500	C14—H14B	0.9900
C3—C4	1.384 (4)	C15—C16	1.525 (4)
C3—H3B	0.9500	C15—H15A	1.0000
C4—C5	1.374 (4)	C16—C17	1.385 (4)
C4—H4A	0.9500	C16—C21	1.386 (4)
C5—C6	1.382 (4)	C17—C18	1.392 (4)
C5—H5A	0.9500	C17—H17A	0.9500
C6—H6A	0.9500	C18—C19	1.384 (4)
C7—C12	1.370 (4)	C18—H18A	0.9500
C7—C8	1.373 (4)	C19—C20	1.376 (5)
C8—C9	1.398 (4)	C19—H19A	0.9500
C8—H8A	0.9500	C20—C21	1.391 (4)
C9—C10	1.370 (5)	C20—H20A	0.9500
C9—H9A	0.9500	C21—H21A	0.9500

O3—P1—O1	113.67 (13)	C10—C11—H11A	119.5
O3—P1—O2	116.68 (12)	C12—C11—H11A	119.5
O1—P1—O2	99.51 (12)	C7—C12—C11	118.5 (3)
O3—P1—N1	114.72 (13)	C7—C12—H12A	120.7
O1—P1—N1	105.78 (13)	C11—C12—H12A	120.7
O2—P1—N1	104.81 (13)	C14—C13—H13A	109.5
C1—O1—P1	128.3 (2)	C14—C13—H13B	109.5
C7—O2—P1	121.73 (19)	H13A—C13—H13B	109.5
C15—N1—P1	120.9 (2)	C14—C13—H13C	109.5
C15—N1—H1	113 (2)	H13A—C13—H13C	109.5
P1—N1—H1	121 (2)	H13B—C13—H13C	109.5
C6—C1—C2	122.1 (3)	C13—C14—C15	113.1 (3)
C6—C1—O1	115.6 (3)	C13—C14—H14A	109.0
C2—C1—O1	122.3 (3)	C15—C14—H14A	109.0
C1—C2—C3	117.9 (3)	C13—C14—H14B	109.0
C1—C2—H2A	121.1	C15—C14—H14B	109.0
C3—C2—H2A	121.1	H14A—C14—H14B	107.8
C4—C3—C2	120.9 (3)	N1—C15—C16	113.0 (3)
C4—C3—H3B	119.6	N1—C15—C14	109.0 (3)
C2—C3—H3B	119.6	C16—C15—C14	111.6 (3)
C5—C4—C3	119.6 (3)	N1—C15—H15A	107.7
C5—C4—H4A	120.2	C16—C15—H15A	107.7
C3—C4—H4A	120.2	C14—C15—H15A	107.7
C4—C5—C6	120.5 (3)	C17—C16—C21	118.0 (3)
C4—C5—H5A	119.7	C17—C16—C15	120.3 (3)
C6—C5—H5A	119.7	C21—C16—C15	121.6 (3)
C1—C6—C5	119.1 (3)	C16—C17—C18	121.4 (3)
C1—C6—H6A	120.5	C16—C17—H17A	119.3
C5—C6—H6A	120.5	C18—C17—H17A	119.3
C12—C7—C8	121.9 (3)	C19—C18—C17	119.3 (3)
C12—C7—O2	119.9 (3)	C19—C18—H18A	120.3
C8—C7—O2	118.0 (3)	C17—C18—H18A	120.3
C7—C8—C9	118.8 (4)	C20—C19—C18	120.4 (3)
C7—C8—H8A	120.6	C20—C19—H19A	119.8
C9—C8—H8A	120.6	C18—C19—H19A	119.8
C10—C9—C8	120.1 (4)	C19—C20—C21	119.6 (3)
C10—C9—H9A	120.0	C19—C20—H20A	120.2
C8—C9—H9A	120.0	C21—C20—H20A	120.2
C9—C10—C11	119.7 (3)	C16—C21—C20	121.3 (3)
C9—C10—H10A	120.1	C16—C21—H21A	119.3
C11—C10—H10A	120.1	C20—C21—H21A	119.3
C10—C11—C12	120.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.84 (1)	2.25 (1)	3.077 (3)	167 (3)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂NO₃P
M_r	367.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	120
a, b, c (Å)	5.4853 (3), 8.1450 (11), 41.162 (4)
V (Å³)	1839.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire2 (large Be window) detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.981, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4914, 3000, 2404
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.089, 1.07
No. of reflections	3000
No. of parameters	239
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.42
Absolute structure	Flack (1983), 1052 Friedel pairs
Absolute structure parameter	−0.09 (14)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), 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···O3ⁱ	0.838 (10)	2.254 (12)	3.077 (3)	167 (3)

Symmetry code: (i) x−1, y, z.

Acknowledgements

Support of this investigation by Islamic Azad University, Zanjan Branch, and Ferdowsi University of Mashhad is gratefully acknowledged.

References

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