N,N′-Dicyclo­hexyl-N′′,N′′-dimethyl­phospho­ric triamide

Sabbaghi, F.; Pourayoubi, M.; Karimi Ahmadabad, F.; Azarkamanzad, Z.; Ebrahimi Valmoozi, A.A.

doi:10.1107/S160053681100287X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o502

doi:10.1107/S160053681100287X

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N,N′-Dicyclohexyl-N′′,N′′-dimethylphosphoric triamide

Fahimeh Sabbaghi,^a ^* Mehrdad Pourayoubi,^b Fatemeh Karimi Ahmadabad,^b Zahra Azarkamanzad ^b and Ali Asghar Ebrahimi Valmoozi ^c

^aDepartment of Chemistry, Islamic Azad University–Zanjan Branch, PO Box 49195-467, Zanjan, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^cDepartment of Chemistry, Tarbiat Modares University, Tehran, Iran
^*Correspondence e-mail: fahimeh_sabbaghi@yahoo.com

(Received 14 January 2011; accepted 21 January 2011; online 26 January 2011)

In the title compound, C₁₄H₃₀N₃OP, both cyclohexyl groups adopt chair conformations with the NH unit in an equatorial position. The P atom adopts a slightly distorted tetrahedral environment. In the (CH₃)₂NP(O) unit, the O—P—N—C torsion angles, showing the orientations of the methyl groups with respect to the phosphoryl group, are −166.6 (3) and 34.6 (4)°. The O atom of the P=O group acts as a double hydrogen-bond acceptor and is involved in two different intermolecular N—H⋯OP hydrogen bonds, building R₂²(8) rings that are further linked into chains running parallel to the b axis.

Related literature

For the structure of a phosphoramidate with a [(CH₃)₂N]P(O) unit, see: Ghadimi et al. (2009 ). For bond distances in related structures, see: Sabbaghi et al. (2010 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ). For double hydrogen-bond acceptors, see: Steiner (2002 ).

Experimental

Crystal data

C₁₄H₃₀N₃OP
M_r = 287.38
Monoclinic, P 2₁ /n
a = 11.742 (4) Å
b = 7.712 (3) Å
c = 18.366 (6) Å
β = 102.120 (7)°
V = 1626.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.23 × 0.19 × 0.13 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.932, T_max = 0.974
11336 measured reflections
3507 independent reflections
1873 reflections with I > 2σ(I)
R_int = 0.103

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.199
S = 1.04
3507 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.90	2.16	3.017 (4)	160
N3—H3⋯O1ⁱⁱ	0.90	2.03	2.911 (4)	165
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681100287X/nc2217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100287X/nc2217Isup2.hkl

checkCIF report

Comment top

The structure determination was performed as a part of a project on the synthesis of new phosphorus compounds having a [(CH₃)₂N]P(O) moiety (Ghadimi et al., 2009).

In the crystal structure of the title compound the two cyclohexyl groups are in a chair conformation with the NH units in equatorial positions (Fig. 1). The P atom is in a slightly distorted tetrahedral environment with bond angles in the range of 100.87 (17)° [N3—P1— N1] to 118.64 (16)° [O1—P1—N3]. In the (CH₃)₂NP(O) moiety, the dihedral angles O—P—N—C are -166.6 (3)° and 34.6 (4)°. The P—N bond lengths are comparable to those in similar compounds like for example in P(O)[NHC(O)C₆H₄(4-NO₂)][NHC₆H₁₁]₂ (Sabbaghi et al., 2010).

The molecules are linked by two intermolecular N—H···OP hydrogen bonds into chains in the direction of the b axis in which the O atom of the P═O group acts as a double H-acceptors (Steiner, 2002) (Fig. 2). From this arrangement R₂²(8) rings are formed (Etter et al., 1990; Bernstein et al., 1995).

Related literature top

For the structure of a phosphoramidate having a [(CH₃)₂N]P(O) unit, see: Ghadimi et al. (2009). For bond distances in related structures, see: Sabbaghi et al. (2010). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995). For double hydrogen-bond acceptors, see: Steiner (2002).

Experimental top

Synthesis of ((CH₃)₂N)P(O)Cl₂ [(CH₃)₂NH₂]Cl (15.00 g, 0.184 mol) and P(O)Cl₃ (84.62 g, 0.552 mol) were refluxed for 8 h and afterwards the excess of P(O)Cl₃ was removed in vacuum.

Synthesis of title compound To a solution of ((CH₃)₂N)P(O)Cl₂ (0.60 g, 3.7 mmol) in chloroform (15 mL), a solution of cyclohexylamine (1.47 g, 14.8 mmol) in chloroform (10 mL) was added at 273 K. After 4 h stirring, the solvent was removed and product was washed with deionized water and recrystallized from chloroform/methanol (4:1 v/v) at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of title compound with labeling and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound with hydrogen bonding shown as dotted lines (the C—H hydrogen atoms are omitted for clarity).

N,N'-Dicyclohexyl-N'',N''-dimethylphosphoric triamide top

Crystal data top

C₁₄H₃₀N₃OP	F(000) = 632
M_r = 287.38	D_x = 1.174 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1063 reflections
a = 11.742 (4) Å	θ = 2.3–26.9°
b = 7.712 (3) Å	µ = 0.17 mm⁻¹
c = 18.366 (6) Å	T = 120 K
β = 102.120 (7)°	Prizm, colorless
V = 1626.0 (10) Å³	0.23 × 0.19 × 0.13 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3507 independent reflections
Radiation source: normal-focus sealed tube	1873 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.103
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −15→14
T_min = 0.932, T_max = 0.974	k = −9→9
11336 measured reflections	l = −23→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.072	Hydrogen site location: mixed
wR(F²) = 0.199	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.062P)² + 2.1669P] where P = (F_o² + 2F_c²)/3
3507 reflections	(Δ/σ)_max < 0.001
174 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₄H₃₀N₃OP	V = 1626.0 (10) Å³
M_r = 287.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.742 (4) Å	µ = 0.17 mm⁻¹
b = 7.712 (3) Å	T = 120 K
c = 18.366 (6) Å	0.23 × 0.19 × 0.13 mm
β = 102.120 (7)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3507 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	1873 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.974	R_int = 0.103
11336 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	0 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.04	Δρ_max = 0.51 e Å⁻³
3507 reflections	Δρ_min = −0.47 e Å⁻³
174 parameters

Special details top

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	0.15685 (9)	0.10911 (13)	0.22176 (6)	0.0231 (3)
O1	0.2842 (2)	0.0799 (3)	0.23095 (15)	0.0261 (6)
N1	0.1077 (3)	0.2079 (4)	0.14150 (19)	0.0287 (8)
N2	0.0944 (3)	−0.0770 (4)	0.23092 (18)	0.0250 (8)
H2	0.1465	−0.1633	0.2435	0.030*
N3	0.1111 (3)	0.2411 (4)	0.27929 (18)	0.0242 (8)
H3	0.1359	0.3518	0.2819	0.029*
C1	0.1595 (4)	0.1671 (6)	0.0782 (2)	0.0385 (11)
H1A	0.1662	0.2733	0.0501	0.058*
H1B	0.1101	0.0834	0.0458	0.058*
H1C	0.2371	0.1170	0.0960	0.058*
C2	−0.0065 (4)	0.2895 (6)	0.1205 (3)	0.0371 (11)
H2A	0.0010	0.4007	0.0961	0.056*
H2B	−0.0381	0.3090	0.1652	0.056*
H2C	−0.0591	0.2135	0.0861	0.056*
C3	−0.0309 (3)	−0.1127 (5)	0.2152 (2)	0.0229 (8)
H3A	−0.0725	−0.0033	0.2230	0.027*
C4	−0.0756 (3)	−0.1728 (5)	0.1348 (2)	0.0281 (9)
H4A	−0.0616	−0.0807	0.1002	0.034*
H4B	−0.0320	−0.2774	0.1252	0.034*
C5	−0.2050 (4)	−0.2142 (6)	0.1202 (2)	0.0302 (10)
H5A	−0.2312	−0.2551	0.0682	0.036*
H5B	−0.2492	−0.1079	0.1264	0.036*
C6	−0.2297 (4)	−0.3535 (5)	0.1737 (2)	0.0299 (10)
H6A	−0.3145	−0.3766	0.1642	0.036*
H6B	−0.1899	−0.4624	0.1651	0.036*
C7	−0.1876 (3)	−0.2957 (5)	0.2534 (2)	0.0279 (9)
H7A	−0.2012	−0.3897	0.2873	0.033*
H7B	−0.2329	−0.1931	0.2631	0.033*
C8	−0.0574 (4)	−0.2497 (5)	0.2699 (2)	0.0272 (9)
H8A	−0.0113	−0.3555	0.2661	0.033*
H8B	−0.0342	−0.2049	0.3214	0.033*
C9	0.1053 (3)	0.1887 (5)	0.3554 (2)	0.0229 (9)
H9A	0.0596	0.0784	0.3517	0.027*
C10	0.0390 (4)	0.3243 (5)	0.3902 (2)	0.0295 (10)
H10A	−0.0386	0.3432	0.3576	0.035*
H10B	0.0819	0.4356	0.3947	0.035*
C11	0.0243 (4)	0.2654 (6)	0.4670 (3)	0.0362 (11)
H11A	−0.0234	0.1586	0.4621	0.043*
H11B	−0.0168	0.3563	0.4895	0.043*
C12	0.1444 (4)	0.2298 (6)	0.5181 (2)	0.0385 (11)
H12A	0.1894	0.3391	0.5268	0.046*
H12B	0.1334	0.1863	0.5669	0.046*
C13	0.2116 (4)	0.0969 (6)	0.4830 (2)	0.0362 (10)
H13A	0.1707	−0.0160	0.4797	0.043*
H13B	0.2900	0.0814	0.5150	0.043*
C14	0.2238 (3)	0.1534 (6)	0.4049 (2)	0.0298 (10)
H14A	0.2720	0.2596	0.4086	0.036*
H14B	0.2637	0.0611	0.3822	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0193 (5)	0.0217 (5)	0.0295 (6)	−0.0005 (4)	0.0079 (4)	−0.0001 (4)
O1	0.0198 (14)	0.0238 (15)	0.0363 (16)	−0.0024 (11)	0.0096 (12)	−0.0017 (12)
N1	0.028 (2)	0.0280 (19)	0.031 (2)	0.0039 (15)	0.0084 (15)	0.0020 (15)
N2	0.0175 (17)	0.0233 (18)	0.0352 (19)	0.0007 (13)	0.0077 (14)	0.0006 (14)
N3	0.0225 (18)	0.0228 (18)	0.0289 (19)	−0.0022 (13)	0.0087 (14)	−0.0016 (14)
C1	0.055 (3)	0.030 (2)	0.034 (3)	0.004 (2)	0.019 (2)	0.0054 (19)
C2	0.033 (3)	0.034 (2)	0.043 (3)	0.006 (2)	0.003 (2)	0.007 (2)
C3	0.0155 (19)	0.0207 (19)	0.033 (2)	−0.0009 (16)	0.0064 (16)	−0.0002 (17)
C4	0.029 (2)	0.027 (2)	0.031 (2)	−0.0042 (18)	0.0119 (18)	−0.0033 (18)
C5	0.026 (2)	0.036 (2)	0.029 (2)	−0.0036 (18)	0.0054 (18)	−0.0019 (18)
C6	0.021 (2)	0.029 (2)	0.041 (3)	−0.0014 (17)	0.0086 (18)	−0.0020 (19)
C7	0.024 (2)	0.025 (2)	0.038 (2)	−0.0022 (17)	0.0133 (18)	0.0024 (18)
C8	0.026 (2)	0.025 (2)	0.031 (2)	0.0017 (17)	0.0058 (17)	0.0008 (17)
C9	0.019 (2)	0.023 (2)	0.029 (2)	−0.0053 (16)	0.0085 (16)	−0.0014 (17)
C10	0.028 (2)	0.026 (2)	0.039 (2)	−0.0008 (18)	0.0164 (19)	0.0023 (18)
C11	0.038 (3)	0.036 (3)	0.041 (3)	0.000 (2)	0.020 (2)	−0.001 (2)
C12	0.046 (3)	0.045 (3)	0.024 (2)	−0.007 (2)	0.006 (2)	−0.002 (2)
C13	0.031 (2)	0.041 (3)	0.036 (2)	−0.005 (2)	0.0048 (19)	0.006 (2)
C14	0.024 (2)	0.031 (2)	0.035 (2)	−0.0026 (17)	0.0082 (18)	0.0004 (18)

Geometric parameters (Å, º) top

P1—O1	1.486 (3)	C6—C7	1.511 (6)
P1—N2	1.636 (3)	C6—H6A	0.9900
P1—N3	1.637 (3)	C6—H6B	0.9900
P1—N1	1.652 (4)	C7—C8	1.536 (6)
N1—C2	1.457 (5)	C7—H7A	0.9900
N1—C1	1.456 (5)	C7—H7B	0.9900
N2—C3	1.465 (5)	C8—H8A	0.9900
N2—H2	0.9000	C8—H8B	0.9900
N3—C9	1.471 (5)	C9—C14	1.518 (5)
N3—H3	0.9000	C9—C10	1.522 (5)
C1—H1A	0.9800	C9—H9A	1.0000
C1—H1B	0.9800	C10—C11	1.526 (6)
C1—H1C	0.9800	C10—H10A	0.9900
C2—H2A	0.9800	C10—H10B	0.9900
C2—H2B	0.9800	C11—C12	1.545 (6)
C2—H2C	0.9800	C11—H11A	0.9900
C3—C4	1.532 (5)	C11—H11B	0.9900
C3—C8	1.534 (5)	C12—C13	1.518 (6)
C3—H3A	1.0000	C12—H12A	0.9900
C4—C5	1.521 (6)	C12—H12B	0.9900
C4—H4A	0.9900	C13—C14	1.535 (6)
C4—H4B	0.9900	C13—H13A	0.9900
C5—C6	1.524 (6)	C13—H13B	0.9900
C5—H5A	0.9900	C14—H14A	0.9900
C5—H5B	0.9900	C14—H14B	0.9900

O1—P1—N2	108.49 (16)	H6A—C6—H6B	108.1
O1—P1—N3	118.64 (16)	C6—C7—C8	111.7 (3)
N2—P1—N3	105.33 (17)	C6—C7—H7A	109.3
O1—P1—N1	109.04 (17)	C8—C7—H7A	109.3
N2—P1—N1	114.59 (17)	C6—C7—H7B	109.3
N3—P1—N1	100.87 (17)	C8—C7—H7B	109.3
C2—N1—C1	113.4 (3)	H7A—C7—H7B	108.0
C2—N1—P1	124.4 (3)	C7—C8—C3	111.1 (3)
C1—N1—P1	119.1 (3)	C7—C8—H8A	109.4
C3—N2—P1	126.7 (3)	C3—C8—H8A	109.4
C3—N2—H2	120.8	C7—C8—H8B	109.4
P1—N2—H2	112.3	C3—C8—H8B	109.4
C9—N3—P1	122.0 (3)	H8A—C8—H8B	108.0
C9—N3—H3	106.8	N3—C9—C14	113.4 (3)
P1—N3—H3	118.5	N3—C9—C10	109.9 (3)
N1—C1—H1A	109.5	C14—C9—C10	111.0 (3)
N1—C1—H1B	109.5	N3—C9—H9A	107.4
H1A—C1—H1B	109.5	C14—C9—H9A	107.4
N1—C1—H1C	109.5	C10—C9—H9A	107.4
H1A—C1—H1C	109.5	C9—C10—C11	110.5 (3)
H1B—C1—H1C	109.5	C9—C10—H10A	109.6
N1—C2—H2A	109.5	C11—C10—H10A	109.6
N1—C2—H2B	109.5	C9—C10—H10B	109.6
H2A—C2—H2B	109.5	C11—C10—H10B	109.6
N1—C2—H2C	109.5	H10A—C10—H10B	108.1
H2A—C2—H2C	109.5	C10—C11—C12	110.5 (3)
H2B—C2—H2C	109.5	C10—C11—H11A	109.6
N2—C3—C4	111.9 (3)	C12—C11—H11A	109.6
N2—C3—C8	109.5 (3)	C10—C11—H11B	109.6
C4—C3—C8	110.3 (3)	C12—C11—H11B	109.6
N2—C3—H3A	108.3	H11A—C11—H11B	108.1
C4—C3—H3A	108.3	C13—C12—C11	110.5 (4)
C8—C3—H3A	108.3	C13—C12—H12A	109.5
C5—C4—C3	111.2 (3)	C11—C12—H12A	109.5
C5—C4—H4A	109.4	C13—C12—H12B	109.5
C3—C4—H4A	109.4	C11—C12—H12B	109.5
C5—C4—H4B	109.4	H12A—C12—H12B	108.1
C3—C4—H4B	109.4	C12—C13—C14	111.4 (4)
H4A—C4—H4B	108.0	C12—C13—H13A	109.3
C4—C5—C6	110.6 (3)	C14—C13—H13A	109.3
C4—C5—H5A	109.5	C12—C13—H13B	109.3
C6—C5—H5A	109.5	C14—C13—H13B	109.3
C4—C5—H5B	109.5	H13A—C13—H13B	108.0
C6—C5—H5B	109.5	C9—C14—C13	110.9 (3)
H5A—C5—H5B	108.1	C9—C14—H14A	109.5
C7—C6—C5	110.4 (3)	C13—C14—H14A	109.5
C7—C6—H6A	109.6	C9—C14—H14B	109.5
C5—C6—H6A	109.6	C13—C14—H14B	109.5
C7—C6—H6B	109.6	H14A—C14—H14B	108.1
C5—C6—H6B	109.6

O1—P1—N1—C2	−166.6 (3)	C3—C4—C5—C6	−58.0 (4)
N2—P1—N1—C2	71.6 (4)	C4—C5—C6—C7	57.8 (4)
N3—P1—N1—C2	−40.9 (4)	C5—C6—C7—C8	−56.5 (4)
O1—P1—N1—C1	34.6 (4)	C6—C7—C8—C3	55.2 (4)
N2—P1—N1—C1	−87.2 (3)	N2—C3—C8—C7	−177.9 (3)
N3—P1—N1—C1	160.2 (3)	C4—C3—C8—C7	−54.3 (4)
O1—P1—N2—C3	−170.3 (3)	P1—N3—C9—C14	65.7 (4)
N3—P1—N2—C3	61.7 (3)	P1—N3—C9—C10	−169.4 (3)
N1—P1—N2—C3	−48.2 (4)	N3—C9—C10—C11	175.8 (3)
O1—P1—N3—C9	−77.8 (3)	C14—C9—C10—C11	−57.9 (4)
N2—P1—N3—C9	43.8 (3)	C9—C10—C11—C12	57.5 (5)
N1—P1—N3—C9	163.3 (3)	C10—C11—C12—C13	−56.5 (5)
P1—N2—C3—C4	91.1 (4)	C11—C12—C13—C14	55.4 (5)
P1—N2—C3—C8	−146.3 (3)	N3—C9—C14—C13	−179.2 (3)
N2—C3—C4—C5	178.3 (3)	C10—C9—C14—C13	56.6 (4)
C8—C3—C4—C5	56.1 (4)	C12—C13—C14—C9	−55.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90	2.16	3.017 (4)	160
N3—H3···O1ⁱⁱ	0.90	2.03	2.911 (4)	165

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

Experimental details

Crystal data
Chemical formula	C₁₄H₃₀N₃OP
M_r	287.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	11.742 (4), 7.712 (3), 18.366 (6)
β (°)	102.120 (7)
V (Å³)	1626.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.23 × 0.19 × 0.13

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.932, 0.974
No. of measured, independent and observed [I > 2σ(I)] reflections	11336, 3507, 1873
R_int	0.103
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.199, 1.04
No. of reflections	3507
No. of parameters	174
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.47

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.90	2.16	3.017 (4)	160
N3—H3···O1ⁱⁱ	0.90	2.03	2.911 (4)	165

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

Acknowledgements

Support of this investigation by Islamic Azad University–Zanjan Branch is gratefully acknowledged.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1998). SAINT-Plus and SMART, Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ghadimi, S., Pourayoubi, M. & Ebrahimi Valmoozi, A. A. (2009). Z. Naturforsch. Teil B, 64, 565–569. CAS 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
Sabbaghi, F., Pourayoubi, M., Toghraee, M. & Divjakovic, V. (2010). Acta Cryst. E66, o344. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steiner, T. (2002). Angew. Chem. Int. Ed. 41, 48–76. Web of Science CrossRef CAS Google Scholar