5-Propyl-6-(p-tolyl­sulfan­yl)pyrimidine-2,4(1H,3H)-dione

Al-Omary, F.A.M.; Ghabbour, H.A.; El-Emam, A.A.; Chidan Kumar, C.S.; Fun, H.-K.

doi:10.1107/S1600536814000749

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 2| February 2014| Pages o179-o180

doi:10.1107/S1600536814000749

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5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione

Fatmah A. M. Al-Omary,^a Hazem A. Ghabbour,^a Ali A. El-Emam,^a ‡ C. S. Chidan Kumar ^b § and Hoong-Kun Fun ^a ^*¶

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riaydh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hfun.c@ksu.edu.sa

(Received 9 January 2014; accepted 11 January 2014; online 22 January 2014)

In the title pymiridine-2,4-dione derivative, C₁₄H₁₆N₂O₂S, the dihedral angle between the six-membered rings is 66.69 (10)°. The molecule is twisted about the C_p—S (p = pyrimidine) bond, with a C—S—C—N torsion angle of −19.57 (16)°. In the crystal, adjacent molecules form inversion dimers through pairs of strong N—H⋯O hydrogen bonds, generating an R₂²(8) ring motif. The dimers are connected into chains extending along the c-axis direction through additional N—H⋯O hydrogen bonds.

CCDC reference: 981111

Related literature

For the pharmacological activity of pyrimidine-2,4-dione derivatives, see: Al-Abdullah et al. (2011 ); El-Emam et al. (2004 ); Hopkins et al. (1996 ); Klein et al. (2001 ); Miyasaka et al. (1989 ); Nencka et al. (2006 ); Russ et al. (2003 ); Tanaka et al. (1995 ); For related pyrimidine-2,4-dione structures, see: El-Brollosy et al. (2009 ); Wang et al. (2006 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For reference bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₆N₂O₂S
M_r = 276.35
Monoclinic, P 2₁ /c
a = 11.8356 (3) Å
b = 10.3040 (2) Å
c = 13.3999 (3) Å
β = 119.850 (2)°
V = 1417.37 (6) Å³
Z = 4
Cu Kα radiation
μ = 2.03 mm⁻¹
T = 293 K
0.82 × 0.71 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.287, T_max = 0.855
9643 measured reflections
2658 independent reflections
2450 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.126
S = 1.06
2658 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O1ⁱ	0.84 (2)	1.98 (2)	2.815 (2)	173 (2)
N1—H1N1⋯O2ⁱⁱ	0.79 (2)	2.17 (2)	2.8988 (18)	155 (2)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 981111

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814000749/sj5382sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814000749/sj5382Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814000749/sj5382Isup3.cml

checkCIF report

Comment top

Pyrimidine-2,4-diones and their related derivatives have long been known for their diverse chemotherapeutic activities including antiviral activity against the HIV (Miyasaka et al., 1989; Tanaka et al., 1995; Hopkins et al., 1996; El-Emam et al., 2004), and HSV viruses (Russ et al., 2003). In addition, potent anticancer activity was observed for several pyrimidine-2,4-diones (Klein et al., 2001; Nencka et al., 2006). In continuation to our interest in the chemical and pharmacological properties of pyrimidine and uracil derivatives (Al-Abdullah et al., 2011; El-Brollosy et al., 2009), we have synthesized the title compound (I) as a potential chemotherapeutic agent.

The title compound (I) is a derivative of pymiridine-2,4-dione. The heterocycle contains the structural unit CON₂H₂CO, forming the dihedral angle of 66.69 (10)° with the adjacent benzene ring. The molecule is bent (Fig. 1) at the S atom with a C–S–C–N torsion angle of -19.57 (16)°. The bond lengths (Allen et al., 1987) and angles in the title compound are within normal ranges and are comparable with those reported earlier (El-Brollosy et al., 2009; Wang et al., 2006). The crystal structure features for two types of intermolecular N–H···O hydrogen bonds (Table 1). Two adjacent molecules form inversion-related dimers through strong N2–H2A···O1 hydrogen bonds (symmetry code: -x + 1, -y, -z + 1), generating an R₂²(8) ring motif (Bernstein et al., 1995) (Fig. 2). These dimers are further connected into chains extending along c axis through additional N1–H1N1···O2 hydrogen bonds (symmetry code: x, -y +1/2, z + 1/2) (Fig. 2). Crystal stability is mainly consolidated by these hydrogen bonding interactions forming two-dimensional networks parallel to the bc plane.

Related literature top

For the pharmacological activity of pyrimidine-2,4-dione derivatives, see: Al-Abdullah et al. (2011); El-Emam et al. (2004); Hopkins et al. (1996); Klein et al. (2001); Miyasaka et al. (1989); Nencka et al. (2006); Russ et al. (2003); Tanaka et al. (1995); For related pyrimidine-2,4-dione structures, see: El-Brollosy et al. (2009); Wang et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond lengths, see: Allen et al. (1987).

Experimental top

A mixture of 6-chloro-5-propyluracil (943 mg, 0.005 mol), p-thiocresol (621 mg, 0.005 mol) and potassium hydroxide (281 mg, 0.005 mol), in ethanol (10 ml), was heated under reflux for 3 h. The solvent was then distilled off in vacuo and the residue was washed with cold water, dried and crystallized from ethanol to yield 995 mg (72%) of the title compound (C₁₄H₁₆N₂O₂S) as colorless needle-like crystals. M·P.: 446–448 K.

¹H NMR (DMSO-d₆, 500.13 MHz): δ 0.84 (t, 3H, CH₂CH₃, J = 7.0 Hz), 1.38–1.40 (m, 2H, CH₂CH₃), 2.31 (s, 3H, Ar—CH₃), 2.44 (t, 2H, CH₂CH₂CH₃, J = 7.0 Hz), 7.22 (d, 2H, Ar—H, J = 7.0 Hz), 7.30 (d, 2H, Ar—H, J = 7.0 Hz), 10.74 (s, 1H, NH), 11.21 (s, 1H, NH). ¹³C NMR (DMSO-d₆, 125.76 MHz): δ 13.73 (CH₂CH₃), 20.54 (CH₂CH₃), 22.05 (CH₂CH₂CH₃), 28.11 (Ar—CH₃), 116.60 (pyrimidine C-5), 128.10, 130.01, 130.18, 130.55 (Ar—C), 143.84 (pyrimidine C-6), 150.46 (C=O), 163.19 (C=O).

Structure description top

For the pharmacological activity of pyrimidine-2,4-dione derivatives, see: Al-Abdullah et al. (2011); El-Emam et al. (2004); Hopkins et al. (1996); Klein et al. (2001); Miyasaka et al. (1989); Nencka et al. (2006); Russ et al. (2003); Tanaka et al. (1995); For related pyrimidine-2,4-dione structures, see: El-Brollosy et al. (2009); Wang et al. (2006). For hydrogen-bond motifs, see: Bernstein et al. (1995). For reference bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom labelling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound, viewed along the b axis, showing the N1–H1N1···O2 and N2–H2N2···O1 intermolecular hydrogen bonds as dashed lines. H-atoms not involved in the hydrogen bonding are omited for clarity.

5-Propyl-6-(p-tolylsulfanyl)pyrimidine-2,4(1H,3H)-dione top

Crystal data top

C₁₄H₁₆N₂O₂S	F(000) = 584
M_r = 276.35	D_x = 1.295 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 5622 reflections
a = 11.8356 (3) Å	θ = 3.8–69.5°
b = 10.3040 (2) Å	µ = 2.03 mm⁻¹
c = 13.3999 (3) Å	T = 293 K
β = 119.850 (2)°	Needle, colourless
V = 1417.37 (6) Å³	0.82 × 0.71 × 0.08 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2658 independent reflections
Radiation source: fine-focus sealed tube	2450 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 69.9°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.287, T_max = 0.855	k = −12→10
9643 measured reflections	l = −16→16

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0707P)² + 0.439P] where P = (F_o² + 2F_c²)/3
2658 reflections	(Δ/σ)_max < 0.001
180 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₄H₁₆N₂O₂S	V = 1417.37 (6) Å³
M_r = 276.35	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.8356 (3) Å	µ = 2.03 mm⁻¹
b = 10.3040 (2) Å	T = 293 K
c = 13.3999 (3) Å	0.82 × 0.71 × 0.08 mm
β = 119.850 (2)°

Data collection top

Bruker APEXII CCD diffractometer	2658 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2450 reflections with I > 2σ(I)
T_min = 0.287, T_max = 0.855	R_int = 0.024
9643 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.33 e Å⁻³
2658 reflections	Δρ_min = −0.39 e Å⁻³
180 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
S1	0.28497 (6)	0.53022 (5)	0.47950 (5)	0.0610 (2)
O1	0.45217 (15)	0.07980 (13)	0.58320 (11)	0.0594 (4)
N1	0.38171 (14)	0.28614 (14)	0.53086 (12)	0.0434 (3)
C1	0.35088 (16)	0.38803 (16)	0.45499 (14)	0.0426 (4)
O2	0.44741 (15)	0.24368 (14)	0.26889 (11)	0.0584 (4)
N2	0.45477 (15)	0.16770 (15)	0.42914 (12)	0.0441 (3)
C2	0.43133 (16)	0.17195 (16)	0.51850 (13)	0.0418 (4)
C3	0.42669 (17)	0.26374 (17)	0.34806 (14)	0.0438 (4)
C4	0.37290 (17)	0.38287 (17)	0.36542 (14)	0.0460 (4)
C5	0.3446 (2)	0.49234 (19)	0.28137 (16)	0.0529 (4)
H5A	0.4150	0.4980	0.2642	0.063*
H5B	0.3424	0.5733	0.3173	0.063*
C6	0.2176 (2)	0.4763 (2)	0.17021 (19)	0.0625 (5)
H6A	0.1478	0.4628	0.1872	0.075*
H6B	0.2225	0.4002	0.1300	0.075*
C7	0.1865 (3)	0.5949 (3)	0.0927 (2)	0.0891 (8)
H7A	0.1054	0.5816	0.0229	0.134*
H7B	0.2547	0.6076	0.0746	0.134*
H7C	0.1800	0.6702	0.1317	0.134*
C8	0.22523 (18)	0.47959 (18)	0.57142 (16)	0.0489 (4)
C9	0.1270 (2)	0.3881 (2)	0.53692 (18)	0.0586 (5)
H9A	0.0937	0.3477	0.4657	0.070*
C10	0.0791 (2)	0.3573 (2)	0.6090 (2)	0.0669 (6)
H10A	0.0149	0.2941	0.5866	0.080*
C11	0.1244 (2)	0.4185 (3)	0.7138 (2)	0.0694 (6)
C12	0.2192 (2)	0.5123 (3)	0.74454 (19)	0.0720 (6)
H12A	0.2485	0.5565	0.8136	0.086*
C13	0.2718 (2)	0.5423 (2)	0.67553 (18)	0.0587 (5)
H13A	0.3376	0.6040	0.6990	0.070*
C14	0.0734 (3)	0.3817 (4)	0.7929 (3)	0.1124 (13)
H14A	0.0086	0.3151	0.7575	0.169*
H14B	0.0353	0.4564	0.8074	0.169*
H14C	0.1438	0.3501	0.8643	0.169*
H2N2	0.483 (2)	0.096 (2)	0.4206 (19)	0.055 (6)*
H1N1	0.3791 (19)	0.291 (2)	0.5883 (19)	0.046 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0879 (4)	0.0444 (3)	0.0701 (4)	0.0183 (2)	0.0541 (3)	0.0103 (2)
O1	0.0977 (10)	0.0498 (7)	0.0494 (7)	0.0248 (7)	0.0507 (7)	0.0134 (6)
N1	0.0588 (8)	0.0447 (8)	0.0356 (7)	0.0101 (6)	0.0303 (6)	0.0027 (6)
C1	0.0483 (8)	0.0411 (9)	0.0399 (8)	0.0035 (7)	0.0231 (7)	0.0013 (7)
O2	0.0888 (9)	0.0579 (8)	0.0487 (7)	0.0058 (7)	0.0494 (7)	0.0040 (6)
N2	0.0609 (8)	0.0421 (8)	0.0392 (7)	0.0091 (6)	0.0323 (7)	0.0029 (6)
C2	0.0523 (8)	0.0434 (9)	0.0335 (7)	0.0081 (7)	0.0243 (7)	0.0018 (7)
C3	0.0545 (9)	0.0461 (9)	0.0367 (8)	−0.0002 (7)	0.0271 (7)	0.0009 (7)
C4	0.0560 (9)	0.0443 (9)	0.0414 (8)	0.0019 (7)	0.0270 (7)	0.0026 (7)
C5	0.0677 (11)	0.0465 (9)	0.0514 (10)	−0.0021 (8)	0.0348 (9)	0.0033 (8)
C6	0.0705 (12)	0.0537 (11)	0.0591 (12)	0.0046 (9)	0.0291 (10)	0.0076 (9)
C7	0.108 (2)	0.0711 (16)	0.0669 (14)	0.0175 (14)	0.0272 (14)	0.0261 (12)
C8	0.0557 (10)	0.0460 (10)	0.0498 (10)	0.0145 (7)	0.0299 (8)	0.0031 (7)
C9	0.0604 (11)	0.0551 (11)	0.0600 (11)	0.0097 (9)	0.0298 (9)	−0.0052 (9)
C10	0.0603 (11)	0.0616 (12)	0.0860 (15)	0.0110 (9)	0.0417 (11)	0.0096 (11)
C11	0.0625 (12)	0.0885 (16)	0.0680 (13)	0.0275 (12)	0.0407 (11)	0.0210 (12)
C12	0.0752 (14)	0.0937 (17)	0.0485 (11)	0.0216 (13)	0.0318 (10)	−0.0030 (11)
C13	0.0596 (11)	0.0623 (12)	0.0544 (11)	0.0090 (9)	0.0285 (9)	−0.0054 (9)
C14	0.099 (2)	0.167 (4)	0.102 (2)	0.038 (2)	0.0731 (19)	0.044 (2)

Geometric parameters (Å, º) top

S1—C1	1.7658 (17)	C6—H6B	0.9700
S1—C8	1.7766 (19)	C7—H7A	0.9600
O1—C2	1.225 (2)	C7—H7B	0.9600
N1—C2	1.361 (2)	C7—H7C	0.9600
N1—C1	1.378 (2)	C8—C13	1.379 (3)
N1—H1N1	0.79 (2)	C8—C9	1.385 (3)
C1—C4	1.350 (2)	C9—C10	1.378 (3)
O2—C3	1.220 (2)	C9—H9A	0.9300
N2—C2	1.358 (2)	C10—C11	1.381 (4)
N2—C3	1.382 (2)	C10—H10A	0.9300
N2—H2N2	0.84 (3)	C11—C12	1.378 (4)
C3—C4	1.454 (2)	C11—C14	1.508 (3)
C4—C5	1.509 (2)	C12—C13	1.383 (3)
C5—C6	1.509 (3)	C12—H12A	0.9300
C5—H5A	0.9700	C13—H13A	0.9300
C5—H5B	0.9700	C14—H14A	0.9600
C6—C7	1.526 (3)	C14—H14B	0.9600
C6—H6A	0.9700	C14—H14C	0.9600

C1—S1—C8	104.50 (8)	C6—C7—H7A	109.5
C2—N1—C1	122.71 (14)	C6—C7—H7B	109.5
C2—N1—H1N1	114.1 (16)	H7A—C7—H7B	109.5
C1—N1—H1N1	122.9 (16)	C6—C7—H7C	109.5
C4—C1—N1	121.90 (15)	H7A—C7—H7C	109.5
C4—C1—S1	119.78 (13)	H7B—C7—H7C	109.5
N1—C1—S1	118.30 (12)	C13—C8—C9	120.23 (19)
C2—N2—C3	126.53 (15)	C13—C8—S1	117.82 (16)
C2—N2—H2N2	114.9 (16)	C9—C8—S1	121.72 (15)
C3—N2—H2N2	118.3 (16)	C10—C9—C8	119.5 (2)
O1—C2—N2	122.78 (15)	C10—C9—H9A	120.3
O1—C2—N1	122.06 (14)	C8—C9—H9A	120.3
N2—C2—N1	115.16 (14)	C9—C10—C11	121.3 (2)
O2—C3—N2	119.25 (16)	C9—C10—H10A	119.3
O2—C3—C4	125.16 (16)	C11—C10—H10A	119.3
N2—C3—C4	115.59 (14)	C12—C11—C10	118.1 (2)
C1—C4—C3	117.98 (15)	C12—C11—C14	121.2 (3)
C1—C4—C5	124.38 (16)	C10—C11—C14	120.8 (3)
C3—C4—C5	117.64 (15)	C11—C12—C13	121.8 (2)
C4—C5—C6	113.39 (16)	C11—C12—H12A	119.1
C4—C5—H5A	108.9	C13—C12—H12A	119.1
C6—C5—H5A	108.9	C8—C13—C12	119.0 (2)
C4—C5—H5B	108.9	C8—C13—H13A	120.5
C6—C5—H5B	108.9	C12—C13—H13A	120.5
H5A—C5—H5B	107.7	C11—C14—H14A	109.5
C5—C6—C7	111.6 (2)	C11—C14—H14B	109.5
C5—C6—H6A	109.3	H14A—C14—H14B	109.5
C7—C6—H6A	109.3	C11—C14—H14C	109.5
C5—C6—H6B	109.3	H14A—C14—H14C	109.5
C7—C6—H6B	109.3	H14B—C14—H14C	109.5
H6A—C6—H6B	108.0

C2—N1—C1—C4	−2.7 (3)	N2—C3—C4—C5	178.08 (16)
C2—N1—C1—S1	179.11 (13)	C1—C4—C5—C6	−99.1 (2)
C8—S1—C1—C4	162.19 (15)	C3—C4—C5—C6	80.5 (2)
C8—S1—C1—N1	−19.57 (16)	C4—C5—C6—C7	174.6 (2)
C3—N2—C2—O1	175.69 (18)	C1—S1—C8—C13	123.21 (15)
C3—N2—C2—N1	−3.8 (3)	C1—S1—C8—C9	−62.23 (17)
C1—N1—C2—O1	−176.24 (17)	C13—C8—C9—C10	−2.0 (3)
C1—N1—C2—N2	3.3 (2)	S1—C8—C9—C10	−176.42 (15)
C2—N2—C3—O2	−176.34 (17)	C8—C9—C10—C11	1.8 (3)
C2—N2—C3—C4	3.4 (3)	C9—C10—C11—C12	0.3 (3)
N1—C1—C4—C3	2.1 (3)	C9—C10—C11—C14	−178.5 (2)
S1—C1—C4—C3	−179.72 (13)	C10—C11—C12—C13	−2.2 (3)
N1—C1—C4—C5	−178.32 (17)	C14—C11—C12—C13	176.6 (2)
S1—C1—C4—C5	−0.1 (2)	C9—C8—C13—C12	0.1 (3)
O2—C3—C4—C1	177.39 (17)	S1—C8—C13—C12	174.76 (16)
N2—C3—C4—C1	−2.3 (2)	C11—C12—C13—C8	2.0 (3)
O2—C3—C4—C5	−2.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1ⁱ	0.84 (2)	1.98 (2)	2.815 (2)	173 (2)
N1—H1N1···O2ⁱⁱ	0.79 (2)	2.17 (2)	2.8988 (18)	155 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1ⁱ	0.84 (2)	1.98 (2)	2.815 (2)	173 (2)
N1—H1N1···O2ⁱⁱ	0.79 (2)	2.17 (2)	2.8988 (18)	155 (2)

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

Footnotes

‡Additonal correspondence author, e-mail: elemam5@hotmail.com.

§Thomson Reuters ResearcherID: C-3194-2011.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center for Female Scientific and Medical Colleges, King Saud University is greatly appreciated. CSCK thanks Universiti Sains Malaysia for a postdoctoral research fellowship.

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