2,2,4-Trimethyl-7-nitro-2,3-dihydro-1H-1,5-benzodiazepin-5-ium perchlorate

Mehdi, S.H.; Sulaiman, O.; Ghalib, R.M.; Yeap, C.S.; Fun, H.-K.

doi:10.1107/S1600536810024475

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1845

doi:10.1107/S1600536810024475

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2,2,4-Trimethyl-7-nitro-2,3-dihydro-1H-1,5-benzodiazepin-5-ium perchlorate

Sayed Hasan Mehdi,^a Othman Sulaiman,^a Raza Murad Ghalib,^a Chin Sing Yeap ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Industrial Technology, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 18 June 2010; accepted 23 June 2010; online 26 June 2010)

In the title molecular salt, C₁₂H₁₆N₃O₂⁺·ClO₄⁻, the nitro group is close to being coplanar with the benzene ring [dihedral angle = 8.1 (3)°]. The seven-membered ring has a maximum deviation of 0.502 (3) Å at the C atom between the dimethyl- and methyl-substituted C atoms. In the crystal, the components are linked into infinite sheets lying parallel to the bc plane by N—H⋯O and C—H⋯O hydrogen bonds. A short O⋯N contact of 2.896 (4) Å occurs within the sheets and a short O⋯O contact of 2.608 (4) Å occurs between the sheets.

Related literature

For general background and applications of benzimidazole derivatives, see: Landquist (1984 ); Insuasty et al. (2010 ); Balakrishna & Kaboudin (2001 ); Ballo et al. (2010 ). For the preparation of the title compound, see: Grech et al. (1994 ). For ring conformations, see Cremer & Pople (1975 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₂H₁₆N₃O₂⁺·ClO₄⁻
M_r = 333.73
Monoclinic, C 2/c
a = 21.046 (7) Å
b = 11.818 (3) Å
c = 15.636 (6) Å
β = 132.176 (9)°
V = 2882.0 (16) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.30 × 0.17 × 0.08 mm

Data collection

Bruker APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.915, T_max = 0.976
24582 measured reflections
3323 independent reflections
2816 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.138
S = 1.05
3323 reflections
210 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.69 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O6ⁱ	0.80 (3)	2.15 (3)	2.941 (3)	173 (3)
N2—H1N2⋯O4	0.82 (5)	2.09 (4)	2.864 (4)	156 (4)
N2—H1N2⋯O4ⁱⁱ	0.82 (5)	2.46 (5)	3.000 (4)	124 (3)
C3—H3A⋯O1ⁱ	0.93	2.51	3.373 (3)	155
C11—H11A⋯O5ⁱ	0.96	2.58	3.524 (3)	169
C11—H11B⋯O3ⁱⁱⁱ	0.96	2.45	3.396 (3)	168
Symmetry codes: (i) $[x, -y+2, z-{\script{1\over 2}}]$ ; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024475/hb5507sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810024475/hb5507Isup2.hkl

checkCIF report

Comment top

Benzodiazepines are interesting compounds due to their wide range of biological activities (Landquist, 1984). Recently many methods have been employed for the synthesis of benzodiazepines derivatives (Insuasty et al., 2010; Balakrishna & Kaboudin, 2001; Ballo et al., 2010). Here we report the synthesis and the crystal structure of title compound.

The asymmetric unit of title compound (Fig. 1) consists of one the benzodiazepinium cation and one perchlorate anion. The nitro group is coplanar with the benzene ring with the dihedral angle of 8.1 (3)°. The seven-membered ring (N1/C1/C6/N2/C7–C9) have a maximum deviation of 0.502 (3) Å at atom C8. In the crystal structure, the molecules are linked into infinite two-dimensional planes parallel to bc plane by the intermolecular N—H···O, C—H···O hydrogen bonds (Table 1) and short O6···N3 interaction of 2.896 (4) Å. Short O2···O3 interaction of 2.608 (4) Å linked these planes into a three-dimensional framewrok (Fig. 2).

Related literature top

For general background and applications of benzimidazoles derivatives, see: Landquist (1984); Insuasty et al. (2010); Balakrishna & Kaboudin (2001); Ballo et al. (2010). For the preparation of the title compound, see: Grech et al. (1994). For ring conformations, see Cremer & Pople (1975). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 4-nitro o-phenylenediamine (0.153 g m) and 4-hydroxy coumarin (0.162 g m) in molar ratio 1:1 was refluxed in a mixture of acetic acid-ethanol (1:1 v/v) for 3 h (Grech et al., 1994). The solid settled in the reaction mixture was filtered and crystallized from ethanol to furnish brownish plates of the unexpected title compound, (I) (55%, m.p. 458 K).

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 (I) with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the c axis, showing the components linked into a 3-D network. Intermolecular hydrogen bonds are shown as dashed lines.

2,2,4-Trimethyl-7-nitro-2,3-dihydro-1H-1,5-benzodiazepin-5-ium perchlorate top

Crystal data top

C₁₂H₁₆N₃O₂⁺·ClO₄⁻	F(000) = 1392
M_r = 333.73	D_x = 1.538 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 7331 reflections
a = 21.046 (7) Å	θ = 2.2–29.8°
b = 11.818 (3) Å	µ = 0.30 mm⁻¹
c = 15.636 (6) Å	T = 100 K
β = 132.176 (9)°	Plate, brown
V = 2882.0 (16) Å³	0.30 × 0.17 × 0.08 mm
Z = 8

Data collection top

Bruker APEXII DUO CCD diffractometer	3323 independent reflections
Radiation source: fine-focus sealed tube	2816 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
T_min = 0.915, T_max = 0.976	k = −15→15
24582 measured reflections	l = −20→20

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0714P)² + 7.0069P] where P = (F_o² + 2F_c²)/3
3323 reflections	(Δ/σ)_max < 0.001
210 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₂H₁₆N₃O₂⁺·ClO₄⁻	V = 2882.0 (16) Å³
M_r = 333.73	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 21.046 (7) Å	µ = 0.30 mm⁻¹
b = 11.818 (3) Å	T = 100 K
c = 15.636 (6) Å	0.30 × 0.17 × 0.08 mm
β = 132.176 (9)°

Data collection top

Bruker APEXII DUO CCD diffractometer	3323 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2816 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.976	R_int = 0.066
24582 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.69 e Å⁻³
3323 reflections	Δρ_min = −0.69 e Å⁻³
210 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Cl1	0.15021 (3)	0.71202 (4)	0.49658 (4)	0.01923 (16)
O1	0.13150 (11)	0.68718 (14)	0.56727 (14)	0.0259 (4)
O2	0.19403 (11)	0.82394 (13)	0.52807 (14)	0.0245 (4)
O3	0.21587 (10)	0.62367 (14)	0.52533 (14)	0.0256 (4)
O4	0.07604 (10)	0.70691 (14)	0.37336 (13)	0.0234 (4)
O5	0.08273 (11)	1.21240 (13)	0.25797 (14)	0.0249 (4)
O6	0.09384 (11)	1.07773 (14)	0.36195 (13)	0.0246 (4)
N1	0.11724 (12)	0.79665 (15)	0.04379 (16)	0.0183 (4)
N2	0.10204 (12)	0.72103 (15)	0.21588 (15)	0.0176 (4)
N3	0.08881 (11)	1.11171 (16)	0.28211 (15)	0.0194 (4)
C1	0.10956 (12)	0.86625 (17)	0.10449 (16)	0.0152 (4)
C2	0.10763 (13)	0.98440 (18)	0.08478 (17)	0.0166 (4)
H2A	0.1127	1.0079	0.0328	0.020*
C3	0.09866 (12)	1.06450 (17)	0.13882 (17)	0.0166 (4)
H3A	0.0967	1.1410	0.1232	0.020*
C4	0.09241 (12)	1.02892 (18)	0.21822 (17)	0.0172 (4)
C5	0.09300 (13)	0.91616 (18)	0.24014 (17)	0.0172 (4)
H5A	0.0872	0.8945	0.2918	0.021*
C6	0.10220 (12)	0.83451 (17)	0.18541 (17)	0.0155 (4)
C7	0.14051 (13)	0.63366 (18)	0.21973 (17)	0.0180 (4)
C8	0.19130 (13)	0.64237 (19)	0.18564 (18)	0.0191 (4)
H8A	0.2184	0.5700	0.1991	0.023*
H8B	0.2364	0.6978	0.2347	0.023*
C9	0.13798 (13)	0.67632 (17)	0.05830 (17)	0.0165 (4)
C10	0.05645 (14)	0.60604 (19)	−0.02308 (18)	0.0216 (4)
H10A	0.0269	0.6260	−0.1015	0.032*
H10B	0.0200	0.6207	−0.0077	0.032*
H10C	0.0710	0.5271	−0.0113	0.032*
C11	0.19389 (15)	0.6604 (2)	0.0295 (2)	0.0234 (5)
H11A	0.1627	0.6841	−0.0485	0.035*
H11B	0.2091	0.5821	0.0377	0.035*
H11C	0.2450	0.7051	0.0813	0.035*
C12	0.13540 (15)	0.52362 (18)	0.26078 (19)	0.0222 (4)
H12A	0.0970	0.5305	0.2738	0.033*
H12B	0.1914	0.5028	0.3315	0.033*
H12C	0.1145	0.4665	0.2035	0.033*
H1N1	0.1130 (16)	0.826 (2)	−0.006 (2)	0.016 (6)*
H1N2	0.0798 (19)	0.715 (2)	0.243 (3)	0.030 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0193 (3)	0.0214 (3)	0.0170 (3)	−0.00116 (18)	0.0122 (2)	−0.00003 (18)
O1	0.0328 (9)	0.0283 (9)	0.0249 (8)	−0.0029 (7)	0.0228 (8)	0.0002 (7)
O2	0.0298 (8)	0.0167 (8)	0.0277 (8)	−0.0057 (6)	0.0195 (7)	−0.0039 (6)
O3	0.0230 (8)	0.0219 (8)	0.0289 (9)	0.0046 (6)	0.0162 (7)	0.0013 (7)
O4	0.0169 (7)	0.0350 (9)	0.0147 (8)	−0.0018 (6)	0.0091 (7)	−0.0003 (6)
O5	0.0305 (9)	0.0176 (8)	0.0253 (8)	0.0029 (6)	0.0183 (7)	0.0006 (6)
O6	0.0319 (9)	0.0267 (8)	0.0192 (8)	0.0026 (7)	0.0188 (7)	0.0002 (6)
N1	0.0239 (9)	0.0180 (9)	0.0167 (9)	0.0012 (7)	0.0152 (8)	0.0019 (7)
N2	0.0186 (8)	0.0192 (9)	0.0156 (8)	−0.0018 (7)	0.0118 (7)	0.0008 (7)
N3	0.0185 (8)	0.0213 (9)	0.0169 (8)	0.0015 (7)	0.0113 (7)	−0.0003 (7)
C1	0.0108 (8)	0.0192 (10)	0.0122 (9)	−0.0005 (7)	0.0064 (7)	−0.0002 (7)
C2	0.0147 (9)	0.0202 (10)	0.0134 (9)	−0.0019 (8)	0.0088 (8)	0.0006 (7)
C3	0.0132 (9)	0.0174 (10)	0.0136 (9)	−0.0013 (7)	0.0067 (8)	0.0001 (7)
C4	0.0146 (9)	0.0204 (10)	0.0141 (9)	0.0014 (8)	0.0087 (8)	−0.0008 (8)
C5	0.0144 (9)	0.0234 (10)	0.0127 (9)	0.0004 (8)	0.0086 (8)	0.0012 (8)
C6	0.0128 (9)	0.0179 (10)	0.0138 (9)	−0.0011 (7)	0.0082 (8)	0.0003 (7)
C7	0.0164 (9)	0.0205 (10)	0.0113 (9)	−0.0025 (8)	0.0069 (8)	0.0003 (7)
C8	0.0159 (9)	0.0220 (10)	0.0172 (10)	0.0016 (8)	0.0102 (8)	0.0027 (8)
C9	0.0162 (9)	0.0164 (9)	0.0174 (10)	0.0013 (8)	0.0115 (8)	0.0018 (8)
C10	0.0209 (10)	0.0231 (11)	0.0182 (10)	−0.0032 (8)	0.0121 (9)	−0.0019 (8)
C11	0.0254 (11)	0.0241 (11)	0.0289 (12)	0.0026 (9)	0.0215 (10)	0.0029 (9)
C12	0.0278 (11)	0.0181 (10)	0.0207 (10)	−0.0013 (9)	0.0163 (9)	0.0017 (8)

Geometric parameters (Å, º) top

Cl1—O1	1.4310 (16)	C4—C5	1.374 (3)
Cl1—O4	1.4538 (16)	C5—C6	1.387 (3)
Cl1—O2	1.4941 (16)	C5—H5A	0.9300
Cl1—O3	1.5388 (17)	C7—C8	1.484 (3)
O5—N3	1.229 (2)	C7—C12	1.486 (3)
O6—N3	1.246 (2)	C8—C9	1.544 (3)
N1—C1	1.345 (3)	C8—H8A	0.9700
N1—C9	1.460 (3)	C8—H8B	0.9700
N1—H1N1	0.79 (3)	C9—C10	1.524 (3)
N2—C7	1.288 (3)	C9—C11	1.528 (3)
N2—C6	1.424 (3)	C10—H10A	0.9600
N2—H1N2	0.81 (3)	C10—H10B	0.9600
N3—C4	1.436 (3)	C10—H10C	0.9600
C1—C6	1.425 (3)	C11—H11A	0.9600
C1—C2	1.425 (3)	C11—H11B	0.9600
C2—C3	1.364 (3)	C11—H11C	0.9600
C2—H2A	0.9300	C12—H12A	0.9600
C3—C4	1.398 (3)	C12—H12B	0.9600
C3—H3A	0.9300	C12—H12C	0.9600

O1—Cl1—O4	114.06 (10)	N2—C7—C8	120.61 (19)
O1—Cl1—O2	110.86 (10)	N2—C7—C12	119.75 (19)
O4—Cl1—O2	110.46 (10)	C8—C7—C12	119.63 (19)
O1—Cl1—O3	107.10 (10)	C7—C8—C9	113.96 (17)
O4—Cl1—O3	108.27 (10)	C7—C8—H8A	108.8
O2—Cl1—O3	105.65 (10)	C9—C8—H8A	108.8
C1—N1—C9	130.62 (18)	C7—C8—H8B	108.8
C1—N1—H1N1	115.8 (19)	C9—C8—H8B	108.8
C9—N1—H1N1	113.4 (19)	H8A—C8—H8B	107.7
C7—N2—C6	128.90 (19)	N1—C9—C10	110.47 (17)
C7—N2—H1N2	118 (2)	N1—C9—C11	106.44 (17)
C6—N2—H1N2	113 (2)	C10—C9—C11	110.21 (18)
O5—N3—O6	122.75 (18)	N1—C9—C8	109.64 (17)
O5—N3—C4	119.30 (18)	C10—C9—C8	111.79 (17)
O6—N3—C4	117.94 (18)	C11—C9—C8	108.13 (17)
N1—C1—C6	127.01 (19)	C9—C10—H10A	109.5
N1—C1—C2	116.50 (18)	C9—C10—H10B	109.5
C6—C1—C2	116.48 (18)	H10A—C10—H10B	109.5
C3—C2—C1	122.82 (19)	C9—C10—H10C	109.5
C3—C2—H2A	118.6	H10A—C10—H10C	109.5
C1—C2—H2A	118.6	H10B—C10—H10C	109.5
C2—C3—C4	118.43 (19)	C9—C11—H11A	109.5
C2—C3—H3A	120.8	C9—C11—H11B	109.5
C4—C3—H3A	120.8	H11A—C11—H11B	109.5
C5—C4—C3	121.52 (19)	C9—C11—H11C	109.5
C5—C4—N3	118.88 (18)	H11A—C11—H11C	109.5
C3—C4—N3	119.55 (19)	H11B—C11—H11C	109.5
C4—C5—C6	120.17 (19)	C7—C12—H12A	109.5
C4—C5—H5A	119.9	C7—C12—H12B	109.5
C6—C5—H5A	119.9	H12A—C12—H12B	109.5
C5—C6—N2	114.60 (18)	C7—C12—H12C	109.5
C5—C6—C1	120.55 (19)	H12A—C12—H12C	109.5
N2—C6—C1	124.83 (18)	H12B—C12—H12C	109.5

C9—N1—C1—C6	−14.5 (3)	C7—N2—C6—C1	31.3 (3)
C9—N1—C1—C2	166.30 (19)	N1—C1—C6—C5	−178.74 (19)
N1—C1—C2—C3	178.87 (18)	C2—C1—C6—C5	0.5 (3)
C6—C1—C2—C3	−0.5 (3)	N1—C1—C6—N2	0.2 (3)
C1—C2—C3—C4	1.0 (3)	C2—C1—C6—N2	179.44 (18)
C2—C3—C4—C5	−1.6 (3)	C6—N2—C7—C8	−2.4 (3)
C2—C3—C4—N3	175.77 (18)	C6—N2—C7—C12	176.47 (19)
O5—N3—C4—C5	−175.37 (19)	N2—C7—C8—C9	−62.3 (3)
O6—N3—C4—C5	6.1 (3)	C12—C7—C8—C9	118.8 (2)
O5—N3—C4—C3	7.1 (3)	C1—N1—C9—C10	97.6 (2)
O6—N3—C4—C3	−171.40 (18)	C1—N1—C9—C11	−142.8 (2)
C3—C4—C5—C6	1.7 (3)	C1—N1—C9—C8	−26.1 (3)
N3—C4—C5—C6	−175.70 (18)	C7—C8—C9—N1	74.8 (2)
C4—C5—C6—N2	179.81 (18)	C7—C8—C9—C10	−48.0 (2)
C4—C5—C6—C1	−1.2 (3)	C7—C8—C9—C11	−169.51 (18)
C7—N2—C6—C5	−149.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O6ⁱ	0.80 (3)	2.15 (3)	2.941 (3)	173 (3)
N2—H1N2···O4	0.82 (5)	2.09 (4)	2.864 (4)	156 (4)
N2—H1N2···O4ⁱⁱ	0.82 (5)	2.46 (5)	3.000 (4)	124 (3)
C3—H3A···O1ⁱ	0.93	2.51	3.373 (3)	155
C11—H11A···O5ⁱ	0.96	2.58	3.524 (3)	169
C11—H11B···O3ⁱⁱⁱ	0.96	2.45	3.396 (3)	168

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₃O₂⁺·ClO₄⁻
M_r	333.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.046 (7), 11.818 (3), 15.636 (6)
β (°)	132.176 (9)
V (Å³)	2882.0 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.30 × 0.17 × 0.08

Data collection
Diffractometer	Bruker APEXII DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.915, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	24582, 3323, 2816
R_int	0.066
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.138, 1.05
No. of reflections	3323
No. of parameters	210
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.69

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O6ⁱ	0.80 (3)	2.15 (3)	2.941 (3)	173 (3)
N2—H1N2···O4	0.82 (5)	2.09 (4)	2.864 (4)	156 (4)
N2—H1N2···O4ⁱⁱ	0.82 (5)	2.46 (5)	3.000 (4)	124 (3)
C3—H3A···O1ⁱ	0.93	2.51	3.373 (3)	155
C11—H11A···O5ⁱ	0.96	2.58	3.524 (3)	169
C11—H11B···O3ⁱⁱⁱ	0.96	2.45	3.396 (3)	168

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

Footnotes

‡Thomson Reuters ResearcherID: A-5523-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

SHM and RMG thank Universiti Sains Malaysia (USM) for the University Grant (1001/PTEKIND/8140152). HKF and CSY thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CSY also thanks USM for the award of a USM Fellowship.

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