(E)-2-(5,5-Dimethyl­hexa­hydro­pyrimidin-2-yl)-4-(phenyl­diazen­yl)phenol

Sheikhshoaie, I.; Monadi, N.; Abbasi, A.

doi:10.1107/S1600536808038877

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2453

doi:10.1107/S1600536808038877

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(E)-2-(5,5-Dimethylhexahydropyrimidin-2-yl)-4-(phenyldiazenyl)phenol

Iran Sheikhshoaie,^a Niaz Monadi ^a and Alireza Abbasi ^b ^*

^aChemistry Department, Shahid Bahonar University, Kerman, Iran, and ^bSchool of Chemistry, University College of Science, University of Tehran, Tehran, Iran
^*Correspondence e-mail: aabbasi@khayam.ut.ac.ir

(Received 18 November 2008; accepted 19 November 2008; online 26 November 2008)

In the title Schiff base, C₁₈H₂₂N₄O, the hexahydropyrimidinyl ring adopts a chair conformation. The dihedral angle between the aromatic rings of the 4-(2-phenyldiazenyl)phenol unit is 15.7 (1)°. There is an intramolecular O—H⋯N hydrogen bond between the hydroxyl group and an N atom of the hexahydropyimidinyl unit. Intermolecular N—H⋯O and N—H⋯N hydrogen bonds give rise to a layer structure.

Related literature

For applications and related structures, see: Farrell et al. (2007 ).

Experimental

Crystal data

C₁₈H₂₂N₄O
M_r = 310.40
Orthorhombic, P b c a
a = 9.0287 (9) Å
b = 12.0767 (12) Å
c = 30.866 (3) Å
V = 3365.5 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 (2) K
0.23 × 0.20 × 0.16 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.970, T_max = 0.987
14483 measured reflections
3134 independent reflections
1574 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.114
S = 0.81
3134 reflections
234 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N3	1.01 (2)	1.65 (2)	2.584 (2)	152 (2)
N3—H3A⋯N4ⁱ	0.92 (2)	2.30 (2)	3.159 (3)	155 (2)
N4—H4A⋯O1ⁱⁱ	0.93 (2)	2.18 (2)	3.106 (3)	172 (2)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038877/ng2518sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038877/ng2518Isup2.hkl

checkCIF report

Comment top

Heterocycles containing nitrogen atoms e.g. hexahydropyrimidines have applications in both inorganic and organic chemistry. Hexahydropyrimidines can be easily prepared from condensations of alkyl diamines and aldehydes. Our interest in synthesizing derivatives of these heterocycles was due to their anti-carcinoma, anti-lymphoma, and anti-biotic properties.

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. Two aromatic rings A (C5—C10) and B (C11—C16) show a little deviation from planarity with a dihedral angle of 15.7 (1)^o. Hexahydropyrimidine has a chair conformation. Intramolecular hydrogen bonds are formed between the phenol hydroxyl groups and the nearest N atom in the hexahydropyimidine groups [O—H···N = 2.584 (2) Å]. The packing of the structure is stabilized by relatively strong N—H···O & N—H···N hydrogen bonds (see Tab. 1), and C—H···π contacts [C—H-cetroid = 2.70 Å] between neighboring molecules. No significant π-π interactions are found in the crystal structure.

Related literature top

For applications and related structures, see: Farrell et al. (2007).

Experimental top

The title compound was prepared via condensation of (E)-5-(2-phenyldiazenyl)-2-hydroxybenzaldehyde and 2,2-dimethylpropane-1,3-diamine in 20 ml EtOH:CHCl3. The mixture solution was stirred and refluxed for 3 h. Colorless prismatic-shape crystals were obtained after evaporation of the excess solvent.

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: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

Fig. 1. Molecular structure of (I), with 50% probability displacement ellipsoids. H atoms are shown as circles of arbitrary radii.

(E)-2-(5,5-Dimethylhexahydropyrimidin-2-yl)-4-(phenyldiazenyl)phenol top

Crystal data top

C₁₈H₂₂N₄O	F(000) = 1328
M_r = 310.40	D_x = 1.225 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 14483 reflections
a = 9.0287 (9) Å	θ = 3–60°
b = 12.0767 (12) Å	µ = 0.08 mm⁻¹
c = 30.866 (3) Å	T = 120 K
V = 3365.5 (6) Å³	Prism, colorless
Z = 8	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3134 independent reflections
Radiation source: fine-focus sealed tube	1574 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.970, T_max = 0.987	k = −14→14
14483 measured reflections	l = −32→37

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	w = 1/[σ²(F_o²) + (0.049P)²] where P = (F_o² + 2F_c²)/3
3134 reflections	(Δ/σ)_max < 0.001
234 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₂₂N₄O	V = 3365.5 (6) Å³
M_r = 310.40	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.0287 (9) Å	µ = 0.08 mm⁻¹
b = 12.0767 (12) Å	T = 120 K
c = 30.866 (3) Å	0.23 × 0.20 × 0.16 mm

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3134 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1574 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.987	R_int = 0.078
14483 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.22 e Å⁻³
3134 reflections	Δρ_min = −0.22 e Å⁻³
234 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
O1	0.69820 (17)	0.17061 (13)	0.26940 (5)	0.0314 (4)
H1A	0.710 (3)	0.121 (2)	0.2433 (7)	0.047*
N1	0.9722 (2)	−0.15729 (17)	0.40388 (6)	0.0301 (5)
N2	0.9051 (2)	−0.06703 (18)	0.41075 (6)	0.0312 (5)
N3	0.7588 (2)	0.00338 (17)	0.22029 (6)	0.0259 (5)
H3A	0.692 (3)	−0.0499 (19)	0.2283 (7)	0.039*
N4	0.9679 (2)	−0.11263 (17)	0.24545 (6)	0.0260 (5)
H4A	0.911 (3)	−0.1732 (19)	0.2543 (7)	0.039*
C1	0.8894 (3)	−0.0082 (2)	0.24903 (7)	0.0237 (6)
H1	0.964 (2)	0.0526 (18)	0.2397 (6)	0.036*
C2	0.8017 (3)	−0.0160 (2)	0.17456 (7)	0.0261 (6)
H21	0.876 (3)	0.0485 (19)	0.1681 (7)	0.039*
H22	0.707 (2)	−0.0077 (18)	0.1561 (7)	0.039*
C3	1.0059 (3)	−0.1371 (2)	0.20003 (8)	0.0277 (6)
H31	1.087 (2)	−0.081 (2)	0.1916 (7)	0.042*
H32	1.048 (2)	−0.212 (2)	0.1986 (7)	0.042*
C4	0.8774 (2)	−0.1275 (2)	0.16755 (7)	0.0265 (6)
C5	0.8460 (2)	0.0185 (2)	0.29537 (7)	0.0237 (6)
C6	0.7534 (2)	0.11069 (19)	0.30298 (7)	0.0244 (6)
C7	0.7169 (3)	0.1417 (2)	0.34482 (7)	0.0306 (6)
H7	0.6563	0.2028	0.3495	0.037*
C8	0.7703 (3)	0.0821 (2)	0.37939 (7)	0.0302 (6)
H8	0.7471	0.1039	0.4075	0.036*
C9	0.8586 (2)	−0.0104 (2)	0.37271 (7)	0.0267 (6)
C10	0.8971 (2)	−0.0407 (2)	0.33038 (7)	0.0261 (6)
H10	0.9581	−0.1017	0.3259	0.031*
C11	1.0190 (3)	−0.2133 (2)	0.44232 (7)	0.0295 (6)
C12	1.0096 (3)	−0.1697 (2)	0.48356 (7)	0.0423 (7)
H12	0.9718	−0.0989	0.4878	0.051*
C13	1.0566 (3)	−0.2317 (3)	0.51851 (8)	0.0508 (8)
H13	1.0503	−0.2024	0.5463	0.061*
C14	1.1127 (3)	−0.3367 (3)	0.51259 (8)	0.0501 (8)
H14	1.1445	−0.3778	0.5363	0.060*
C15	1.1217 (3)	−0.3807 (3)	0.47163 (8)	0.0481 (8)
H15	1.1587	−0.4518	0.4676	0.058*
C16	1.0754 (3)	−0.3187 (2)	0.43638 (8)	0.0404 (7)
H16	1.0822	−0.3481	0.4086	0.049*
C17	0.7683 (3)	−0.22207 (19)	0.17308 (7)	0.0326 (6)
H17A	0.7266	−0.2195	0.2017	0.049*
H17B	0.8186	−0.2913	0.1690	0.049*
H17C	0.6905	−0.2152	0.1520	0.049*
C18	0.9416 (3)	−0.1313 (2)	0.12165 (7)	0.0371 (7)
H18A	0.8627	−0.1258	0.1009	0.056*
H18B	0.9936	−0.1998	0.1175	0.056*
H18C	1.0089	−0.0705	0.1177	0.056*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0319 (10)	0.0309 (11)	0.0312 (10)	0.0044 (8)	0.0002 (8)	0.0017 (8)
N1	0.0269 (12)	0.0339 (13)	0.0294 (12)	−0.0031 (11)	−0.0025 (9)	0.0034 (10)
N2	0.0262 (12)	0.0355 (13)	0.0320 (12)	−0.0021 (11)	−0.0005 (10)	0.0029 (10)
N3	0.0220 (11)	0.0308 (13)	0.0249 (11)	−0.0014 (10)	−0.0025 (9)	0.0016 (10)
N4	0.0241 (12)	0.0288 (12)	0.0250 (11)	−0.0012 (10)	0.0007 (9)	0.0020 (10)
C1	0.0190 (13)	0.0262 (14)	0.0259 (13)	0.0022 (12)	−0.0040 (11)	0.0008 (11)
C2	0.0242 (14)	0.0292 (15)	0.0250 (14)	0.0024 (12)	0.0000 (11)	0.0011 (11)
C3	0.0239 (14)	0.0315 (16)	0.0277 (14)	0.0011 (12)	−0.0007 (11)	−0.0021 (12)
C4	0.0236 (13)	0.0310 (15)	0.0250 (13)	−0.0040 (12)	−0.0002 (11)	0.0021 (11)
C5	0.0173 (12)	0.0276 (14)	0.0260 (13)	−0.0033 (11)	−0.0014 (10)	−0.0003 (11)
C6	0.0205 (13)	0.0237 (14)	0.0290 (13)	−0.0048 (11)	0.0002 (12)	0.0031 (11)
C7	0.0286 (15)	0.0290 (15)	0.0342 (15)	0.0004 (12)	0.0018 (12)	−0.0032 (12)
C8	0.0282 (15)	0.0328 (15)	0.0297 (14)	−0.0045 (13)	0.0040 (12)	−0.0040 (11)
C9	0.0241 (14)	0.0308 (15)	0.0251 (13)	−0.0072 (12)	−0.0008 (11)	0.0014 (11)
C10	0.0203 (13)	0.0284 (15)	0.0295 (14)	−0.0005 (11)	−0.0008 (11)	−0.0008 (11)
C11	0.0282 (14)	0.0354 (16)	0.0250 (14)	−0.0024 (13)	−0.0027 (11)	0.0050 (12)
C12	0.0562 (19)	0.0416 (18)	0.0292 (15)	−0.0041 (15)	−0.0075 (14)	0.0021 (14)
C13	0.066 (2)	0.058 (2)	0.0279 (15)	−0.0043 (18)	−0.0083 (14)	0.0001 (15)
C14	0.055 (2)	0.063 (2)	0.0325 (17)	−0.0007 (17)	−0.0086 (15)	0.0163 (15)
C15	0.0481 (19)	0.050 (2)	0.0462 (18)	0.0091 (16)	−0.0025 (15)	0.0125 (15)
C16	0.0401 (17)	0.0511 (19)	0.0300 (15)	0.0032 (15)	−0.0031 (13)	0.0007 (13)
C17	0.0339 (15)	0.0339 (16)	0.0299 (13)	0.0007 (13)	−0.0056 (12)	−0.0002 (11)
C18	0.0368 (16)	0.0435 (17)	0.0310 (14)	0.0005 (14)	0.0038 (12)	−0.0007 (13)

Geometric parameters (Å, º) top

O1—C6	1.358 (2)	C7—C8	1.375 (3)
O1—H1A	1.01 (2)	C7—H7	0.9300
N1—N2	1.265 (3)	C8—C9	1.387 (3)
N1—C11	1.429 (3)	C8—H8	0.9300
N2—C9	1.422 (3)	C9—C10	1.401 (3)
N3—C2	1.482 (3)	C10—H10	0.9300
N3—C1	1.483 (3)	C11—C12	1.380 (3)
N3—H3A	0.92 (2)	C11—C16	1.384 (3)
N4—C1	1.451 (3)	C12—C13	1.380 (3)
N4—C3	1.473 (3)	C12—H12	0.9300
N4—H4A	0.93 (2)	C13—C14	1.377 (4)
C1—C5	1.518 (3)	C13—H13	0.9300
C1—H1	1.04 (2)	C14—C15	1.374 (3)
C2—C4	1.525 (3)	C14—H14	0.9300
C2—H21	1.05 (2)	C15—C16	1.385 (3)
C2—H22	1.03 (2)	C15—H15	0.9300
C3—C4	1.537 (3)	C16—H16	0.9300
C3—H31	1.03 (2)	C17—H17A	0.9600
C3—H32	0.98 (2)	C17—H17B	0.9600
C4—C17	1.518 (3)	C17—H17C	0.9600
C4—C18	1.531 (3)	C18—H18A	0.9600
C5—C10	1.375 (3)	C18—H18B	0.9600
C5—C6	1.412 (3)	C18—H18C	0.9600
C6—C7	1.385 (3)

C6—O1—H1A	104.5 (13)	C6—C7—H7	120.1
N2—N1—C11	114.21 (19)	C7—C8—C9	120.5 (2)
N1—N2—C9	114.67 (19)	C7—C8—H8	119.7
C2—N3—C1	110.27 (18)	C9—C8—H8	119.7
C2—N3—H3A	108.7 (14)	C8—C9—C10	119.4 (2)
C1—N3—H3A	107.3 (14)	C8—C9—N2	115.7 (2)
C1—N4—C3	111.13 (19)	C10—C9—N2	124.8 (2)
C1—N4—H4A	113.1 (14)	C5—C10—C9	120.9 (2)
C3—N4—H4A	104.4 (14)	C5—C10—H10	119.5
N4—C1—N3	115.15 (19)	C9—C10—H10	119.5
N4—C1—C5	112.51 (19)	C12—C11—C16	119.7 (2)
N3—C1—C5	109.76 (18)	C12—C11—N1	124.5 (2)
N4—C1—H1	106.2 (12)	C16—C11—N1	115.7 (2)
N3—C1—H1	106.5 (12)	C11—C12—C13	119.6 (3)
C5—C1—H1	106.1 (11)	C11—C12—H12	120.2
N3—C2—C4	113.06 (19)	C13—C12—H12	120.2
N3—C2—H21	103.4 (12)	C14—C13—C12	120.6 (2)
C4—C2—H21	110.0 (13)	C14—C13—H13	119.7
N3—C2—H22	107.0 (12)	C12—C13—H13	119.7
C4—C2—H22	112.2 (13)	C15—C14—C13	120.0 (3)
H21—C2—H22	110.8 (17)	C15—C14—H14	120.0
N4—C3—C4	115.46 (19)	C13—C14—H14	120.0
N4—C3—H31	105.8 (12)	C14—C15—C16	119.8 (3)
C4—C3—H31	108.8 (12)	C14—C15—H15	120.1
N4—C3—H32	108.5 (13)	C16—C15—H15	120.1
C4—C3—H32	109.2 (13)	C11—C16—C15	120.3 (2)
H31—C3—H32	108.9 (18)	C11—C16—H16	119.9
C17—C4—C2	110.9 (2)	C15—C16—H16	119.9
C17—C4—C18	109.10 (19)	C4—C17—H17A	109.5
C2—C4—C18	109.10 (19)	C4—C17—H17B	109.5
C17—C4—C3	111.07 (19)	H17A—C17—H17B	109.5
C2—C4—C3	108.18 (19)	C4—C17—H17C	109.5
C18—C4—C3	108.39 (19)	H17A—C17—H17C	109.5
C10—C5—C6	118.6 (2)	H17B—C17—H17C	109.5
C10—C5—C1	122.9 (2)	C4—C18—H18A	109.5
C6—C5—C1	118.5 (2)	C4—C18—H18B	109.5
O1—C6—C7	118.7 (2)	H18A—C18—H18B	109.5
O1—C6—C5	120.7 (2)	C4—C18—H18C	109.5
C7—C6—C5	120.6 (2)	H18A—C18—H18C	109.5
C8—C7—C6	119.9 (2)	H18B—C18—H18C	109.5
C8—C7—H7	120.1

C11—N1—N2—C9	179.73 (19)	O1—C6—C7—C8	179.6 (2)
C3—N4—C1—N3	52.1 (3)	C5—C6—C7—C8	−0.4 (3)
C3—N4—C1—C5	178.90 (19)	C6—C7—C8—C9	−1.2 (4)
C2—N3—C1—N4	−55.2 (3)	C7—C8—C9—C10	2.1 (3)
C2—N3—C1—C5	176.64 (19)	C7—C8—C9—N2	−178.7 (2)
C1—N3—C2—C4	55.4 (3)	N1—N2—C9—C8	173.0 (2)
C1—N4—C3—C4	−50.2 (3)	N1—N2—C9—C10	−7.9 (3)
N3—C2—C4—C17	69.7 (2)	C6—C5—C10—C9	−0.1 (3)
N3—C2—C4—C18	−170.09 (19)	C1—C5—C10—C9	177.5 (2)
N3—C2—C4—C3	−52.4 (3)	C8—C9—C10—C5	−1.4 (3)
N4—C3—C4—C17	−71.9 (3)	N2—C9—C10—C5	179.4 (2)
N4—C3—C4—C2	50.1 (3)	N2—N1—C11—C12	−7.3 (3)
N4—C3—C4—C18	168.3 (2)	N2—N1—C11—C16	171.9 (2)
N4—C1—C5—C10	10.1 (3)	C16—C11—C12—C13	0.0 (4)
N3—C1—C5—C10	139.7 (2)	N1—C11—C12—C13	179.2 (2)
N4—C1—C5—C6	−172.34 (19)	C11—C12—C13—C14	0.0 (4)
N3—C1—C5—C6	−42.7 (3)	C12—C13—C14—C15	−0.3 (4)
C10—C5—C6—O1	−178.9 (2)	C13—C14—C15—C16	0.6 (4)
C1—C5—C6—O1	3.4 (3)	C12—C11—C16—C15	0.3 (4)
C10—C5—C6—C7	1.0 (3)	N1—C11—C16—C15	−179.0 (2)
C1—C5—C6—C7	−176.7 (2)	C14—C15—C16—C11	−0.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	1.01 (2)	1.65 (2)	2.584 (2)	152 (2)
N3—H3A···N4ⁱ	0.92 (2)	2.30 (2)	3.159 (3)	155 (2)
N4—H4A···O1ⁱⁱ	0.93 (2)	2.18 (2)	3.106 (3)	172 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₄O
M_r	310.40
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	120
a, b, c (Å)	9.0287 (9), 12.0767 (12), 30.866 (3)
V (Å³)	3365.5 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.23 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.970, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	14483, 3134, 1574
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.114, 0.81
No. of reflections	3134
No. of parameters	234
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.22

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N3	1.01 (2)	1.65 (2)	2.584 (2)	152 (2)
N3—H3A···N4ⁱ	0.92 (2)	2.30 (2)	3.159 (3)	155 (2)
N4—H4A···O1ⁱⁱ	0.93 (2)	2.18 (2)	3.106 (3)	172 (2)

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

Acknowledgements

This work was supported by a grant from the University of Kerman and the University of Tehran.

References

Brandenburg, K. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SAINT-Plus and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrell, J. R., Niconchuk, J., Higham, C. S. & Bergeron, B. W. (2007). Tetrahedron Lett. 48, 8034–8036. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). 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
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar