1-[(Z)-2-Phenyl­hydrazin-1-yl­idene]-1-(piperidin-1-yl)propan-2-one

Abdel-Aziz, H.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811029680

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2172

doi:10.1107/S1600536811029680

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1-[(Z)-2-Phenylhydrazin-1-ylidene]-1-(piperidin-1-yl)propan-2-one

Hatem A. Abdel-Aziz,^a ‡ Seik Weng Ng ^c,^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 21 July 2011; accepted 22 July 2011; online 30 July 2011)

A Z configuration about the imine bond [1.3025 (18) Å] in the title compound, C₁₄H₁₉N₃O, allows for the formation of an intramoleclar N—H⋯N hydrogen bond between the hydrazone H and piperidine N atoms; the carbonyl group is disposed to lie over the piperidine residue, which is in a chair form. A twist between the terminal benzene ring and the hydrazine residue is seen [N—N—C—C torsion angle = 163.81 (12)°]. Helical supramolecular chains along the c axis mediated by N—H⋯O hydrogen bonds are the most prominent feature of the crystal packing. The chains are connected into layers lying in the ac plane by weak C—H⋯π contacts involving two methylene H atoms and an adjacent benzene ring.

Related literature

For background to the biological activity of amidrazones, see: Frohberg et al. (2006 ); Abdel-Aziz & Mekawey (2009 ); Abdel-Aziz et al. (2010 ). For the synthesis, see: Frohberg et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₉N₃O
M_r = 245.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1195 (2) Å
b = 11.9614 (2) Å
c = 12.0393 (2) Å
V = 1313.27 (4) Å³
Z = 4
Cu Kα radiation
μ = 0.64 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.857, T_max = 0.969
5335 measured reflections
2589 independent reflections
2482 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.05
2589 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 1077 Friedel pairs
Flack parameter: −0.1 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9–C14 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3⋯N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b⋯Cg1ⁱⁱ	0.99	2.77	3.5535 (16)	137
C3—H3a⋯Cg1ⁱⁱⁱ	0.99	2.98	3.9473 (16)	167
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2010); 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: 10.1107/S1600536811029680/hb6327sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029680/hb6327Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029680/hb6327Isup3.cml

checkCIF report

Comment top

The title compound (I) and related amidrazone derivatives are known to possess biological activity (Frohberg et al., 2006), the motivation for on-going studies in this area (Abdel-Aziz & Mekawey, 2009; Abdel-Aziz et al., 2010). In the molecule of (I), Fig. 1, the configuration about the imine N2═C6 bond [1.3025 (18) Å] is Z. This places the hydrazone-N3—H in close proximity to the piperidinyl-N1 enabling the formation of an intramolecular N—H···N hydrogen bond (Table 1). The carbonyl group is disposed to lie over the piperidinyl group which adopts a chair conformation. The benzene group is twisted out of the plane through the hydrazine residue to which it is connected as seen in the value of the N2—N3—C9—C10 torsion angle of 163.81 (12) °. The piperidinyl group is disposed to be almost normal to the rest of the molecule so that the dihedral plane formed through its least-squares plane and that through the O1,N2,N3,C6,C7,C9 atoms is 85.26 (6) °.

In the crystal, molecules are connected into a helical supramolecular chain mediated by N—H···O hydrogen bonds (Table 1). Chains are orientated along the c axis and are connected into a supramolecular array in the ac plane by C—H···π interactions involving methylene-H atoms associated with the bifurcated benzene ring (Table 1 and Fig. 2).

Related literature top

For background to the biological activity of amidrazones, see: Frohberg et al. (2006); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al. (2010). For the synthesis, see: Frohberg et al. (1995).

Experimental top

This compound was prepared by the reaction of 2-oxo-N'-phenylpropanehydrazonoyl chloride with piperidine (Frohberg et al., 1995). The yellow prisms of (I) were isolated from its ethanol solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular array aligned in the ac plane in (I) mediated by N—H···O and C—H···π interactions shown as orange and purple dashed lines, respectively.

1-[(Z)-2-Phenylhydrazin-1-ylidene]-1-(piperidin-1-yl)propan-2-one top

Crystal data top

C₁₄H₁₉N₃O	F(000) = 528
M_r = 245.32	D_x = 1.241 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3524 reflections
a = 9.1195 (2) Å	θ = 3.7–73.9°
b = 11.9614 (2) Å	µ = 0.64 mm⁻¹
c = 12.0393 (2) Å	T = 100 K
V = 1313.27 (4) Å³	Prism, yellow
Z = 4	0.25 × 0.10 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2589 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2482 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.1°, θ_min = 5.2°
ω scans	h = −11→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −14→11
T_min = 0.857, T_max = 0.969	l = −15→13
5335 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)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0415P)² + 0.2381P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2589 reflections	Δρ_max = 0.12 e Å⁻³
168 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1077 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.1 (3)

Crystal data top

C₁₄H₁₉N₃O	V = 1313.27 (4) Å³
M_r = 245.32	Z = 4
Orthorhombic, P2₁2₁2₁	Cu Kα radiation
a = 9.1195 (2) Å	µ = 0.64 mm⁻¹
b = 11.9614 (2) Å	T = 100 K
c = 12.0393 (2) Å	0.25 × 0.10 × 0.05 mm

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2589 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2482 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.969	R_int = 0.021
5335 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.080	Δρ_max = 0.12 e Å⁻³
S = 1.05	Δρ_min = −0.20 e Å⁻³
2589 reflections	Absolute structure: Flack (1983), 1077 Friedel pairs
168 parameters	Absolute structure parameter: −0.1 (3)
0 restraints

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	0.78315 (11)	0.39621 (8)	0.41136 (8)	0.0206 (2)
N1	0.76810 (12)	0.50948 (9)	0.20177 (9)	0.0152 (2)
N2	0.55012 (12)	0.40406 (10)	0.18282 (10)	0.0161 (2)
N3	0.52865 (13)	0.46113 (10)	0.08925 (10)	0.0176 (2)
C1	0.91802 (15)	0.46592 (12)	0.18446 (12)	0.0180 (3)
H1A	0.9139	0.3963	0.1401	0.022*
H1B	0.9634	0.4482	0.2571	0.022*
C2	1.01007 (16)	0.55293 (12)	0.12398 (12)	0.0212 (3)
H2A	0.9713	0.5632	0.0479	0.025*
H2B	1.1123	0.5258	0.1179	0.025*
C3	1.00881 (16)	0.66502 (12)	0.18456 (13)	0.0221 (3)
H3A	1.0614	0.6576	0.2561	0.027*
H3B	1.0606	0.7216	0.1392	0.027*
C4	0.85187 (16)	0.70368 (12)	0.20604 (13)	0.0219 (3)
H4A	0.8531	0.7729	0.2510	0.026*
H4B	0.8031	0.7205	0.1345	0.026*
C5	0.76669 (16)	0.61340 (11)	0.26713 (12)	0.0201 (3)
H5A	0.8116	0.5999	0.3408	0.024*
H5B	0.6643	0.6382	0.2788	0.024*
C6	0.66729 (15)	0.42747 (11)	0.24015 (11)	0.0159 (3)
C7	0.68611 (15)	0.36763 (12)	0.34649 (11)	0.0172 (3)
C8	0.58735 (18)	0.27024 (12)	0.37224 (12)	0.0236 (3)
H8A	0.5897	0.2550	0.4522	0.035*
H8B	0.6212	0.2041	0.3316	0.035*
H8C	0.4868	0.2882	0.3497	0.035*
C9	0.40458 (15)	0.43897 (11)	0.02405 (11)	0.0158 (3)
C10	0.36359 (15)	0.51634 (12)	−0.05636 (11)	0.0177 (3)
H10	0.4195	0.5825	−0.0668	0.021*
C11	0.24038 (16)	0.49645 (13)	−0.12146 (11)	0.0215 (3)
H11	0.2126	0.5490	−0.1768	0.026*
C12	0.15788 (17)	0.40034 (14)	−0.10604 (12)	0.0246 (3)
H12	0.0731	0.3875	−0.1500	0.030*
C13	0.19957 (17)	0.32311 (13)	−0.02621 (13)	0.0249 (3)
H13	0.1434	0.2570	−0.0160	0.030*
C14	0.32279 (16)	0.34171 (12)	0.03888 (12)	0.0206 (3)
H14	0.3512	0.2884	0.0933	0.025*
H3	0.596 (2)	0.5100 (15)	0.0692 (16)	0.029 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0199 (5)	0.0240 (5)	0.0178 (5)	−0.0002 (4)	−0.0022 (4)	−0.0007 (4)
N1	0.0118 (5)	0.0150 (5)	0.0189 (5)	−0.0006 (4)	0.0002 (4)	−0.0004 (4)
N2	0.0153 (5)	0.0165 (5)	0.0166 (5)	0.0009 (5)	0.0010 (4)	−0.0002 (5)
N3	0.0141 (5)	0.0204 (6)	0.0184 (5)	−0.0045 (5)	−0.0016 (5)	0.0037 (5)
C1	0.0147 (6)	0.0190 (7)	0.0203 (6)	0.0023 (5)	0.0022 (6)	−0.0026 (6)
C2	0.0151 (6)	0.0244 (7)	0.0241 (7)	−0.0003 (6)	0.0043 (6)	0.0018 (6)
C3	0.0162 (7)	0.0221 (7)	0.0280 (7)	−0.0048 (6)	0.0004 (6)	0.0034 (6)
C4	0.0192 (7)	0.0167 (6)	0.0297 (7)	−0.0018 (6)	0.0014 (6)	0.0011 (6)
C5	0.0179 (7)	0.0167 (6)	0.0255 (7)	0.0009 (6)	0.0043 (6)	−0.0022 (6)
C6	0.0141 (6)	0.0156 (6)	0.0178 (6)	−0.0004 (5)	0.0020 (5)	−0.0018 (5)
C7	0.0170 (7)	0.0175 (7)	0.0171 (6)	0.0024 (5)	0.0017 (5)	−0.0029 (5)
C8	0.0299 (8)	0.0211 (7)	0.0199 (7)	−0.0047 (6)	−0.0008 (6)	0.0031 (6)
C9	0.0117 (6)	0.0187 (7)	0.0171 (6)	0.0002 (5)	0.0004 (5)	−0.0039 (5)
C10	0.0154 (6)	0.0203 (6)	0.0175 (6)	0.0000 (5)	0.0019 (5)	−0.0023 (5)
C11	0.0177 (7)	0.0286 (8)	0.0181 (6)	0.0044 (6)	−0.0001 (5)	−0.0019 (6)
C12	0.0156 (6)	0.0342 (8)	0.0241 (7)	−0.0019 (6)	−0.0052 (6)	−0.0072 (6)
C13	0.0192 (7)	0.0248 (7)	0.0307 (8)	−0.0061 (6)	−0.0009 (6)	−0.0047 (6)
C14	0.0180 (7)	0.0191 (7)	0.0247 (7)	−0.0034 (6)	−0.0014 (6)	−0.0006 (6)

Geometric parameters (Å, º) top

O1—C7	1.2288 (17)	C4—H4B	0.9900
N1—C6	1.4216 (17)	C5—H5A	0.9900
N1—C5	1.4712 (17)	C5—H5B	0.9900
N1—C1	1.4778 (17)	C6—C7	1.4767 (19)
N2—C6	1.3025 (18)	C7—C8	1.505 (2)
N2—N3	1.3317 (16)	C8—H8A	0.9800
N3—C9	1.4023 (17)	C8—H8B	0.9800
N3—H3	0.88 (2)	C8—H8C	0.9800
C1—C2	1.523 (2)	C9—C10	1.391 (2)
C1—H1A	0.9900	C9—C14	1.3934 (19)
C1—H1B	0.9900	C10—C11	1.390 (2)
C2—C3	1.526 (2)	C10—H10	0.9500
C2—H2A	0.9900	C11—C12	1.386 (2)
C2—H2B	0.9900	C11—H11	0.9500
C3—C4	1.526 (2)	C12—C13	1.386 (2)
C3—H3A	0.9900	C12—H12	0.9500
C3—H3B	0.9900	C13—C14	1.388 (2)
C4—C5	1.5201 (19)	C13—H13	0.9500
C4—H4A	0.9900	C14—H14	0.9500

C6—N1—C5	113.80 (10)	N1—C5—H5B	109.7
C6—N1—C1	113.63 (10)	C4—C5—H5B	109.7
C5—N1—C1	112.42 (10)	H5A—C5—H5B	108.2
C6—N2—N3	117.31 (11)	N2—C6—N1	120.44 (12)
N2—N3—C9	119.69 (11)	N2—C6—C7	116.78 (12)
N2—N3—H3	118.1 (13)	N1—C6—C7	122.75 (12)
C9—N3—H3	122.1 (13)	O1—C7—C6	119.99 (13)
N1—C1—C2	109.67 (11)	O1—C7—C8	121.03 (12)
N1—C1—H1A	109.7	C6—C7—C8	118.96 (12)
C2—C1—H1A	109.7	C7—C8—H8A	109.5
N1—C1—H1B	109.7	C7—C8—H8B	109.5
C2—C1—H1B	109.7	H8A—C8—H8B	109.5
H1A—C1—H1B	108.2	C7—C8—H8C	109.5
C1—C2—C3	111.58 (12)	H8A—C8—H8C	109.5
C1—C2—H2A	109.3	H8B—C8—H8C	109.5
C3—C2—H2A	109.3	C10—C9—C14	120.06 (13)
C1—C2—H2B	109.3	C10—C9—N3	118.74 (12)
C3—C2—H2B	109.3	C14—C9—N3	121.20 (13)
H2A—C2—H2B	108.0	C11—C10—C9	119.72 (13)
C4—C3—C2	110.75 (12)	C11—C10—H10	120.1
C4—C3—H3A	109.5	C9—C10—H10	120.1
C2—C3—H3A	109.5	C10—C11—C12	120.33 (14)
C4—C3—H3B	109.5	C10—C11—H11	119.8
C2—C3—H3B	109.5	C12—C11—H11	119.8
H3A—C3—H3B	108.1	C13—C12—C11	119.78 (13)
C5—C4—C3	110.24 (12)	C13—C12—H12	120.1
C5—C4—H4A	109.6	C11—C12—H12	120.1
C3—C4—H4A	109.6	C12—C13—C14	120.44 (14)
C5—C4—H4B	109.6	C12—C13—H13	119.8
C3—C4—H4B	109.6	C14—C13—H13	119.8
H4A—C4—H4B	108.1	C13—C14—C9	119.66 (14)
N1—C5—C4	109.69 (11)	C13—C14—H14	120.2
N1—C5—H5A	109.7	C9—C14—H14	120.2
C4—C5—H5A	109.7

C6—N2—N3—C9	179.73 (12)	N2—C6—C7—O1	−170.31 (12)
C6—N1—C1—C2	169.70 (11)	N1—C6—C7—O1	7.84 (19)
C5—N1—C1—C2	−59.23 (15)	N2—C6—C7—C8	11.11 (18)
N1—C1—C2—C3	54.55 (15)	N1—C6—C7—C8	−170.74 (13)
C1—C2—C3—C4	−53.17 (16)	N2—N3—C9—C10	163.81 (12)
C2—C3—C4—C5	54.34 (16)	N2—N3—C9—C14	−16.06 (19)
C6—N1—C5—C4	−167.80 (11)	C14—C9—C10—C11	0.3 (2)
C1—N1—C5—C4	61.21 (15)	N3—C9—C10—C11	−179.57 (12)
C3—C4—C5—N1	−57.74 (16)	C9—C10—C11—C12	0.4 (2)
N3—N2—C6—N1	−1.12 (18)	C10—C11—C12—C13	−0.8 (2)
N3—N2—C6—C7	177.07 (11)	C11—C12—C13—C14	0.4 (2)
C5—N1—C6—N2	108.74 (14)	C12—C13—C14—C9	0.3 (2)
C1—N1—C6—N2	−120.87 (13)	C10—C9—C14—C13	−0.7 (2)
C5—N1—C6—C7	−69.34 (15)	N3—C9—C14—C13	179.22 (13)
C1—N1—C6—C7	61.04 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3···N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b···Cg1ⁱⁱ	0.99	2.77	3.5535 (16)	137
C3—H3a···Cg1ⁱⁱⁱ	0.99	2.98	3.9473 (16)	167

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₉N₃O
M_r	245.32
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.1195 (2), 11.9614 (2), 12.0393 (2)
V (Å³)	1313.27 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.64
Crystal size (mm)	0.25 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.857, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	5335, 2589, 2482
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.05
No. of reflections	2589
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.20
Absolute structure	Flack (1983), 1077 Friedel pairs
Absolute structure parameter	−0.1 (3)

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

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C9–C14 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.88 (2)	2.47 (2)	3.2317 (15)	145.6 (17)
N3—H3···N1	0.88 (2)	2.242 (19)	2.6340 (16)	106.8 (15)
C2—H2b···Cg1ⁱⁱ	0.99	2.77	3.5535 (16)	137
C3—H3a···Cg1ⁱⁱⁱ	0.99	2.98	3.9473 (16)	167

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

Footnotes

‡Additional correspondence author, e-mail: hatem_741@yahoo.com.

Acknowledgements

The authors thank King Saud University and the University of Malaya for supporting this study.

References

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Volume 67| Part 8| August 2011| Page o2172

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