N-(3-Amino­bicyclo­[2.2.1]heptan-2-yl)-4-methyl­benzene­sulfonamide

Abdel-Aziz, A.A.-M.; El-Azab, A.S.; El-Sherbeny, M.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812025421

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2032

https://doi.org/10.1107/S1600536812025421

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N-(3-Aminobicyclo[2.2.1]heptan-2-yl)-4-methylbenzenesulfonamide

Alaa A.-M. Abdel-Aziz,^a,^b ‡ Adel S. El-Azab,^a,^c Magda A. El-Sherbeny,^b Seik Weng Ng ^d,^e and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^cDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 1 June 2012; accepted 5 June 2012; online 13 June 2012)

In the title compound, C₁₄H₂₀N₂O₂S, the sulfonamide O atoms lie to one side of the benzene ring and the aminobicycloheptanyl to the other side [C_ar—S—N—C torsion angle = −57.93 (11)°; ar = aromatic]. An intramolecular N—H⋯N hydrogen bond is formed. In the crystal, a supramolecular chain is formed along the b axis via N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For chiral ligands in asymmetric catalytic reactions, see: Seo et al. (2001 ); Abdel-Aziz et al. (2004 ); Matsunaga et al. (2005 ); Yamakuchi et al. (2005 ).

Experimental

Crystal data

C₁₄H₂₀N₂O₂S
M_r = 280.38
Monoclinic, P 2₁
a = 10.1715 (2) Å
b = 6.1169 (1) Å
c = 11.5150 (3) Å
β = 110.332 (2)°
V = 671.80 (2) Å³
Z = 2
Cu Kα radiation
μ = 2.14 mm⁻¹
T = 100 K
0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.566, T_max = 0.814
4721 measured reflections
2750 independent reflections
2731 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.066
S = 1.03
2750 reflections
185 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1217 Friedel pairs
Flack parameter: −0.001 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1n⋯O1ⁱ	0.88 (1)	2.20 (1)	2.976 (2)	148 (2)
N1—H2n⋯N2	0.87 (1)	2.39 (2)	2.752 (2)	105 (2)
N2—H3n⋯N1ⁱ	0.89 (1)	2.04 (1)	2.907 (2)	166 (2)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+2]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025421/lh5485sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025421/lh5485Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025421/lh5485Isup3.cml

checkCIF report

Comment top

The title compound (I) was synthesized in the context of the development of chiral ligands for asymmetric catalytic reactions (Seo et al., 2001; Abdel-Aziz et al., 2004; Matsunaga et al., 2005; Yamakuchi et al. 2005).

In (I), Fig. 1, the two S-bound O atoms lie to one side of the adjacent benzene ring with the O1 and O2 atoms lying -0.466 (1) and -0.771 (1) Å out of the plane, respectively, and the aminobicycloheptanyl residue lying to the other side, the C8—S1—N2—C2 torsion being -57.93 (11)°. An intramolecular N—H···N hydrogen bond is noted, Table 1.

Molecules are connected into a supramolecular chain along the b axis via N—H···O and N—H···N hydrogen bonds that generate 12-membered {···HNC₂NH···OSNC₂N} synthons, Fig. 2 and Table 1. The chains pack into a three-dimensional architecture without specific interactions between them, Fig. 3.

Related literature top

For chiral ligands in asymmetric catalytic reactions, see: Seo et al. (2001); Abdel-Aziz et al. (2004); Matsunaga et al. (2005); Yamakuchi et al. (2005).

Experimental top

To the mixture of 2-imidazolidinone (2.0 ml), water (2 ml), ethanol (6 ml) and Ba(OH)₂.8H₂O (20 ml) were added. This was heated at 413 K in a glass sealed tube for 24 h. The solvents were evaporated and the precipitate extracted three times with chloroform (10 ml × 3). The organic extract was dried and crystallized from ethanol to afford the title compound.

Structure description top

For chiral ligands in asymmetric catalytic reactions, see: Seo et al. (2001); Abdel-Aziz et al. (2004); Matsunaga et al. (2005); Yamakuchi et al. (2005).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the supramolecular helical chain along the b axis in (I). The N—H···O and N—H···N hydrogen bonds are shown as orange and blue dashed lines, respectively.
	Fig. 3. A view in projection down the b axis of the unit-cell contents for (I). The N—H···O and N—H···N (obscured) hydrogen bonds are shown as orange and blue dashed lines, respectively.

N-(3-Aminobicyclo[2.2.1]heptan-2-yl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₄H₂₀N₂O₂S	F(000) = 300
M_r = 280.38	D_x = 1.386 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 3574 reflections
a = 10.1715 (2) Å	θ = 4.1–76.4°
b = 6.1169 (1) Å	µ = 2.14 mm⁻¹
c = 11.5150 (3) Å	T = 100 K
β = 110.332 (2)°	Prism, colourless
V = 671.80 (2) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2750 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2731 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.014
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.6°, θ_min = 4.1°
ω scan	h = −11→12
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −7→7
T_min = 0.566, T_max = 0.814	l = −14→12
4721 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)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.049P)² + 0.0858P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2750 reflections	Δρ_max = 0.22 e Å⁻³
185 parameters	Δρ_min = −0.26 e Å⁻³
4 restraints	Absolute structure: Flack (1983), 1217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.001 (10)

Crystal data top

C₁₄H₂₀N₂O₂S	V = 671.80 (2) Å³
M_r = 280.38	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 10.1715 (2) Å	µ = 2.14 mm⁻¹
b = 6.1169 (1) Å	T = 100 K
c = 11.5150 (3) Å	0.30 × 0.20 × 0.10 mm
β = 110.332 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	2750 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2731 reflections with I > 2σ(I)
T_min = 0.566, T_max = 0.814	R_int = 0.014
4721 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.066	Δρ_max = 0.22 e Å⁻³
S = 1.03	Δρ_min = −0.26 e Å⁻³
2750 reflections	Absolute structure: Flack (1983), 1217 Friedel pairs
185 parameters	Absolute structure parameter: −0.001 (10)
4 restraints

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

	x	y	z	U_iso*/U_eq
S1	0.26041 (3)	0.50378 (5)	0.72818 (2)	0.01602 (9)
O1	0.26695 (10)	0.73734 (17)	0.71708 (9)	0.0218 (2)
N1	0.52705 (11)	0.5254 (2)	1.10027 (10)	0.0184 (2)
N2	0.32587 (11)	0.44016 (18)	0.87334 (10)	0.0160 (2)
O2	0.32988 (10)	0.36603 (18)	0.66642 (9)	0.0215 (2)
C1	0.38324 (13)	0.5685 (2)	1.09495 (11)	0.0168 (3)
H1	0.3790	0.7246	1.1192	0.020*
C2	0.26899 (13)	0.5369 (2)	0.96230 (11)	0.0153 (2)
H2	0.2286	0.6832	0.9304	0.018*
C3	0.15457 (14)	0.4000 (2)	0.98927 (13)	0.0190 (3)
H3	0.0587	0.4149	0.9256	0.023*
C4	0.16743 (13)	0.4842 (3)	1.11857 (12)	0.0224 (3)
H4A	0.1085	0.4015	1.1559	0.027*
H4B	0.1486	0.6429	1.1196	0.027*
C5	0.32467 (14)	0.4279 (2)	1.17705 (12)	0.0198 (3)
H5	0.3666	0.4604	1.2676	0.024*
C6	0.32835 (14)	0.1852 (2)	1.14384 (13)	0.0213 (3)
H6A	0.3138	0.0901	1.2079	0.026*
H6B	0.4187	0.1470	1.1345	0.026*
C7	0.20485 (14)	0.1631 (2)	1.01838 (13)	0.0220 (3)
H7A	0.2373	0.1024	0.9533	0.026*
H7B	0.1296	0.0687	1.0268	0.026*
C8	0.07959 (14)	0.4382 (2)	0.67418 (11)	0.0164 (2)
C9	−0.01687 (14)	0.6042 (2)	0.66650 (12)	0.0200 (3)
H9	0.0144	0.7488	0.6912	0.024*
C10	−0.15935 (14)	0.5562 (2)	0.62230 (12)	0.0205 (3)
H10	−0.2253	0.6691	0.6170	0.025*
C11	−0.20671 (13)	0.3446 (2)	0.58568 (12)	0.0185 (3)
C12	−0.10771 (14)	0.1807 (2)	0.59531 (12)	0.0190 (3)
H12	−0.1387	0.0356	0.5715	0.023*
C13	0.03540 (14)	0.2258 (2)	0.63911 (12)	0.0180 (3)
H13	0.1017	0.1131	0.6449	0.022*
C14	−0.36173 (14)	0.2973 (3)	0.53354 (14)	0.0244 (3)
H14A	−0.4059	0.3911	0.4615	0.037*
H14B	−0.4036	0.3264	0.5969	0.037*
H14C	−0.3765	0.1436	0.5083	0.037*
H1n	0.5811 (16)	0.480 (3)	1.1733 (11)	0.025 (4)*
H2n	0.530 (2)	0.412 (2)	1.0552 (16)	0.033 (5)*
H3n	0.357 (2)	0.3032 (19)	0.882 (2)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01351 (14)	0.01864 (15)	0.01503 (14)	−0.00197 (11)	0.00386 (10)	−0.00003 (11)
O1	0.0213 (5)	0.0204 (5)	0.0199 (5)	−0.0048 (4)	0.0026 (4)	0.0027 (4)
N1	0.0138 (5)	0.0199 (5)	0.0187 (5)	−0.0012 (5)	0.0021 (4)	0.0008 (5)
N2	0.0140 (5)	0.0182 (5)	0.0151 (5)	0.0023 (4)	0.0040 (4)	0.0002 (4)
O2	0.0177 (5)	0.0296 (5)	0.0185 (4)	0.0000 (4)	0.0081 (4)	−0.0028 (4)
C1	0.0169 (6)	0.0155 (6)	0.0161 (6)	0.0013 (4)	0.0032 (4)	−0.0005 (4)
C2	0.0141 (5)	0.0153 (6)	0.0160 (5)	0.0026 (4)	0.0046 (4)	0.0002 (5)
C3	0.0133 (6)	0.0223 (6)	0.0217 (6)	0.0008 (5)	0.0064 (5)	0.0013 (5)
C4	0.0201 (6)	0.0266 (7)	0.0240 (6)	0.0055 (6)	0.0122 (5)	0.0031 (6)
C5	0.0196 (6)	0.0226 (6)	0.0176 (6)	0.0041 (5)	0.0069 (5)	0.0024 (5)
C6	0.0198 (6)	0.0204 (7)	0.0259 (7)	0.0021 (5)	0.0106 (5)	0.0057 (5)
C7	0.0180 (6)	0.0197 (6)	0.0306 (7)	−0.0037 (5)	0.0113 (5)	0.0006 (6)
C8	0.0151 (6)	0.0188 (6)	0.0141 (6)	−0.0009 (5)	0.0036 (4)	0.0007 (4)
C9	0.0195 (6)	0.0174 (6)	0.0216 (6)	−0.0002 (5)	0.0053 (5)	−0.0012 (5)
C10	0.0178 (6)	0.0217 (7)	0.0216 (6)	0.0033 (5)	0.0063 (5)	0.0020 (5)
C11	0.0155 (6)	0.0247 (7)	0.0146 (6)	−0.0006 (5)	0.0041 (5)	0.0001 (5)
C12	0.0189 (6)	0.0183 (6)	0.0177 (6)	−0.0022 (5)	0.0037 (5)	−0.0010 (5)
C13	0.0171 (6)	0.0182 (6)	0.0175 (6)	0.0023 (5)	0.0046 (5)	−0.0003 (5)
C14	0.0154 (6)	0.0326 (8)	0.0238 (7)	−0.0015 (5)	0.0049 (5)	−0.0024 (6)

Geometric parameters (Å, º) top

S1—O2	1.4367 (10)	C5—H5	1.0000
S1—O1	1.4380 (11)	C6—C7	1.556 (2)
S1—N2	1.6172 (11)	C6—H6A	0.9900
S1—C8	1.7707 (13)	C6—H6B	0.9900
N1—C1	1.4665 (16)	C7—H7A	0.9900
N1—H1n	0.875 (9)	C7—H7B	0.9900
N1—H2n	0.873 (9)	C8—C13	1.3884 (18)
N2—C2	1.4649 (16)	C8—C9	1.3930 (19)
N2—H3n	0.888 (9)	C9—C10	1.3902 (18)
C1—C5	1.5425 (18)	C9—H9	0.9500
C1—C2	1.5771 (16)	C10—C11	1.394 (2)
C1—H1	1.0000	C10—H10	0.9500
C2—C3	1.5502 (18)	C11—C12	1.3977 (19)
C2—H2	1.0000	C11—C14	1.5076 (18)
C3—C7	1.5347 (19)	C12—C13	1.3925 (19)
C3—C4	1.5376 (19)	C12—H12	0.9500
C3—H3	1.0000	C13—H13	0.9500
C4—C5	1.5432 (18)	C14—H14A	0.9800
C4—H4A	0.9900	C14—H14B	0.9800
C4—H4B	0.9900	C14—H14C	0.9800
C5—C6	1.537 (2)

O2—S1—O1	119.52 (6)	C6—C5—H5	114.4
O2—S1—N2	105.89 (6)	C1—C5—H5	114.4
O1—S1—N2	108.41 (6)	C4—C5—H5	114.4
O2—S1—C8	108.84 (6)	C5—C6—C7	103.51 (11)
O1—S1—C8	105.56 (6)	C5—C6—H6A	111.1
N2—S1—C8	108.23 (6)	C7—C6—H6A	111.1
C1—N1—H1n	112.5 (12)	C5—C6—H6B	111.1
C1—N1—H2n	111.1 (13)	C7—C6—H6B	111.1
H1n—N1—H2n	100.2 (18)	H6A—C6—H6B	109.0
C2—N2—S1	120.32 (9)	C3—C7—C6	102.75 (11)
C2—N2—H3n	120.9 (14)	C3—C7—H7A	111.2
S1—N2—H3n	110.2 (14)	C6—C7—H7A	111.2
N1—C1—C5	117.79 (10)	C3—C7—H7B	111.2
N1—C1—C2	114.02 (10)	C6—C7—H7B	111.2
C5—C1—C2	102.34 (10)	H7A—C7—H7B	109.1
N1—C1—H1	107.4	C13—C8—C9	120.92 (13)
C5—C1—H1	107.4	C13—C8—S1	120.39 (10)
C2—C1—H1	107.4	C9—C8—S1	118.69 (11)
N2—C2—C3	115.36 (10)	C10—C9—C8	119.41 (13)
N2—C2—C1	112.93 (10)	C10—C9—H9	120.3
C3—C2—C1	102.95 (10)	C8—C9—H9	120.3
N2—C2—H2	108.4	C9—C10—C11	120.88 (13)
C3—C2—H2	108.4	C9—C10—H10	119.6
C1—C2—H2	108.4	C11—C10—H10	119.6
C7—C3—C4	101.26 (11)	C10—C11—C12	118.56 (12)
C7—C3—C2	109.72 (11)	C10—C11—C14	120.16 (13)
C4—C3—C2	101.29 (10)	C12—C11—C14	121.25 (13)
C7—C3—H3	114.4	C13—C12—C11	121.36 (13)
C4—C3—H3	114.4	C13—C12—H12	119.3
C2—C3—H3	114.4	C11—C12—H12	119.3
C3—C4—C5	94.26 (10)	C8—C13—C12	118.85 (12)
C3—C4—H4A	112.9	C8—C13—H13	120.6
C5—C4—H4A	112.9	C12—C13—H13	120.6
C3—C4—H4B	112.9	C11—C14—H14A	109.5
C5—C4—H4B	112.9	C11—C14—H14B	109.5
H4A—C4—H4B	110.3	H14A—C14—H14B	109.5
C6—C5—C1	109.75 (11)	C11—C14—H14C	109.5
C6—C5—C4	102.60 (11)	H14A—C14—H14C	109.5
C1—C5—C4	99.82 (10)	H14B—C14—H14C	109.5

O2—S1—N2—C2	−174.49 (10)	C1—C5—C6—C7	−74.78 (12)
O1—S1—N2—C2	56.10 (11)	C4—C5—C6—C7	30.64 (13)
C8—S1—N2—C2	−57.93 (11)	C4—C3—C7—C6	−39.25 (12)
S1—N2—C2—C3	93.87 (12)	C2—C3—C7—C6	67.22 (13)
S1—N2—C2—C1	−148.11 (9)	C5—C6—C7—C3	5.12 (13)
N1—C1—C2—N2	8.26 (15)	O2—S1—C8—C13	32.18 (13)
C5—C1—C2—N2	−120.07 (12)	O1—S1—C8—C13	161.63 (11)
N1—C1—C2—C3	133.32 (11)	N2—S1—C8—C13	−82.46 (12)
C5—C1—C2—C3	5.00 (12)	O2—S1—C8—C9	−147.16 (10)
N2—C2—C3—C7	49.21 (14)	O1—S1—C8—C9	−17.71 (12)
C1—C2—C3—C7	−74.26 (12)	N2—S1—C8—C9	98.19 (11)
N2—C2—C3—C4	155.65 (10)	C13—C8—C9—C10	−0.4 (2)
C1—C2—C3—C4	32.18 (12)	S1—C8—C9—C10	178.91 (10)
C7—C3—C4—C5	56.71 (12)	C8—C9—C10—C11	0.0 (2)
C2—C3—C4—C5	−56.28 (12)	C9—C10—C11—C12	0.5 (2)
N1—C1—C5—C6	−58.83 (14)	C9—C10—C11—C14	−177.73 (12)
C2—C1—C5—C6	67.07 (12)	C10—C11—C12—C13	−0.68 (19)
N1—C1—C5—C4	−166.13 (11)	C14—C11—C12—C13	177.57 (12)
C2—C1—C5—C4	−40.23 (12)	C9—C8—C13—C12	0.3 (2)
C3—C4—C5—C6	−53.44 (12)	S1—C8—C13—C12	−179.03 (10)
C3—C4—C5—C1	59.52 (12)	C11—C12—C13—C8	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.88 (1)	2.20 (1)	2.976 (2)	148 (2)
N1—H2n···N2	0.87 (1)	2.39 (2)	2.752 (2)	105 (2)
N2—H3n···N1ⁱ	0.89 (1)	2.04 (1)	2.907 (2)	166 (2)

Symmetry code: (i) −x+1, y−1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₀N₂O₂S
M_r	280.38
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	100
a, b, c (Å)	10.1715 (2), 6.1169 (1), 11.5150 (3)
β (°)	110.332 (2)
V (Å³)	671.80 (2)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.14
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.566, 0.814
No. of measured, independent and observed [I > 2σ(I)] reflections	4721, 2750, 2731
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.066, 1.03
No. of reflections	2750
No. of parameters	185
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26
Absolute structure	Flack (1983), 1217 Friedel pairs
Absolute structure parameter	−0.001 (10)

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1n···O1ⁱ	0.88 (1)	2.20 (1)	2.976 (2)	148 (2)
N1—H2n···N2	0.87 (1)	2.39 (2)	2.752 (2)	105 (2)
N2—H3n···N1ⁱ	0.89 (1)	2.04 (1)	2.907 (2)	166 (2)

Symmetry code: (i) −x+1, y−1/2, −z+2.

Footnotes

‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.

Acknowledgements

The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work. They also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM·C/HIR/MOHE/SC/12).

References

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