Triethyl­ammonium 4-nitro­benzene­sulfonate

Al-Dajani, M.T.M.; Abdallah, H.H.; Mohamed, N.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810021379

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1647

doi:10.1107/S1600536810021379

Open

access

Triethylammonium 4-nitrobenzenesulfonate

Mohammad T. M. Al-Dajani,^a Hassan H. Abdallah,^b Nornisah Mohamed,^a ‡ Ching Kheng Quah ^c § and Hoong-Kun Fun ^c ^*¶

^aSchool of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 1 June 2010; accepted 4 June 2010; online 16 June 2010)

In the anion of the title molecular salt, C₆H₁₆N⁺·C₆H₄O₅S⁻, the nitro group is twisted slightly from the benzene ring, making a dihedral angle of 3.16 (10)°. In the crystal structure, the cations and anions are linked into a two-dimensional network parallel to the ab plane by C—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For general background to and the synthesis of the title compound, see: Dann & Davies (1929 ); D'Souza et al. (2008 ); Hunig et al. (1965 ); Kim et al. (1999 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For a related structure, see: Quah et al. (2008 ).

Experimental

Crystal data

C₆H₁₆N⁺·C₆H₄NO₅S⁻
M_r = 304.36
Orthorhombic, P b c a
a = 7.8015 (14) Å
b = 12.669 (2) Å
c = 29.910 (6) Å
V = 2956.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.22 × 0.18 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.950, T_max = 0.967
21787 measured reflections
5605 independent reflections
3985 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.01
5605 reflections
261 parameters
All H-atom parameters refined
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O4	0.95 (2)	1.86 (2)	2.7899 (17)	166 (2)
C2—H2A⋯O5ⁱ	0.96 (2)	2.485 (19)	3.1000 (19)	121.7 (14)
C7—H7B⋯O4ⁱⁱ	1.00 (2)	2.50 (2)	3.4081 (19)	151.3 (16)
C10—H10B⋯O3ⁱⁱⁱ	0.96 (2)	2.59 (2)	3.461 (2)	151.1 (18)
C12—H12A⋯O5ⁱⁱⁱ	0.99 (2)	2.60 (2)	3.559 (2)	164.1 (16)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) x+1, y, z.

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/S1600536810021379/wn2392sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021379/wn2392Isup2.hkl

checkCIF report

Comment top

Aromatic nitro sulfonyl compounds are very important since they can be used as raw materials for the manufacture of sulfanilamide preparations. o-Nitrobenzenesulfonylhydrazide (NBSH) is a very important reagent for the synthesis of allenes from propargylic alcohols. The preparation of NBSH from o-nitrobenzenesulfonyl chloride and hydrazine in benzene was described in 1929 by Dann and Davies (Dann & Davies, 1929; D'Souza et al., 2008; Hunig et al., 1965; Kim et al., 1999).

The asymmetric unit (Fig. 1) of the title compound contains one triethylammonium cation and one 4-nitrobenzenesulfonate anion. A proton transfer from the sulfonic acid group of 4-nitrobenzenesulfonic acid to atom N2 of triethylamine resulted in the formation of ions. In the anion, the nitro group is twisted slightly from the attached ring; the dihedral angle between the C1—C6 and O1/O2/N1/C1 planes is 3.16 (10)°. The bond lengths and angles in the 4-nitrobenzenesulfonate anion are within normal ranges and similar to those in a comparable crystal structure (Quah et al., 2008). In the crystal structure, the cations and anions are linked to form a two-dimensional network (Fig. 2) parallel to the ab-plane by C—H···O and N—H···O hydrogen bonds (Table 1).

Related literature top

For general background to and the synthesis of the title compound, see: Dann & Davies (1929); D'Souza et al. (2008); Hunig et al. (1965); Kim et al. (1999). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For a related structure, see: Quah et al. (2008).

Experimental top

4-Nitrobenzenesulfonyl chloride (0.01 mol, 2.05 g) was dissolved in 25 ml of tetrahydrofuran (THF) in a round-bottomed flask with stirring. Triethylamine (0.01 mol, 0.70 g) was mixed with some THF and added to the flask dropwise with stirring. The reaction mixture was refluxed for 2.5 h and left at room temperature overnight. The needle crystals that were formed were then filtered off, washed with water and dried at 353 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 structures of the two ions of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. The crystal structure of the title compound viewed along the c axis. H atoms not involved in intermolecular interactions (dashed lines) have been omitted for clarity.

Triethylammonium 4-nitrobenzenesulfonate top

Crystal data top

C₆H₁₆N⁺·C₆H₄NO₅S⁻	F(000) = 1296
M_r = 304.36	D_x = 1.368 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2801 reflections
a = 7.8015 (14) Å	θ = 2.7–30.9°
b = 12.669 (2) Å	µ = 0.24 mm⁻¹
c = 29.910 (6) Å	T = 100 K
V = 2956.3 (9) Å³	Block, yellow
Z = 8	0.22 × 0.18 × 0.14 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5605 independent reflections
Radiation source: fine-focus sealed tube	3985 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ϕ and ω scans	θ_max = 33.2°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→12
T_min = 0.950, T_max = 0.967	k = −9→19
21787 measured reflections	l = −40→46

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) = 0.135	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0731P)²] where P = (F_o² + 2F_c²)/3
5605 reflections	(Δ/σ)_max < 0.001
261 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₆H₁₆N⁺·C₆H₄NO₅S⁻	V = 2956.3 (9) Å³
M_r = 304.36	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.8015 (14) Å	µ = 0.24 mm⁻¹
b = 12.669 (2) Å	T = 100 K
c = 29.910 (6) Å	0.22 × 0.18 × 0.14 mm

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	5605 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3985 reflections with I > 2σ(I)
T_min = 0.950, T_max = 0.967	R_int = 0.064
21787 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	All H-atom parameters refined
S = 1.01	Δρ_max = 0.55 e Å⁻³
5605 reflections	Δρ_min = −0.47 e Å⁻³
261 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
S1	0.38577 (5)	0.17193 (3)	0.095990 (11)	0.01330 (9)
O1	0.2417 (3)	−0.17343 (11)	0.26000 (4)	0.0524 (5)
O2	0.37185 (19)	−0.05239 (12)	0.29767 (4)	0.0372 (3)
O3	0.25347 (14)	0.13583 (9)	0.06573 (3)	0.0195 (2)
O4	0.55993 (14)	0.14889 (8)	0.07988 (3)	0.0172 (2)
O5	0.36886 (15)	0.28080 (8)	0.11063 (4)	0.0206 (2)
N1	0.3145 (2)	−0.08793 (12)	0.26271 (4)	0.0265 (3)
C1	0.3331 (2)	−0.02431 (12)	0.22174 (5)	0.0184 (3)
C2	0.2606 (2)	−0.06215 (11)	0.18258 (5)	0.0174 (3)
C3	0.27633 (19)	−0.00053 (11)	0.14418 (5)	0.0157 (3)
C4	0.36392 (18)	0.09467 (10)	0.14563 (4)	0.0134 (2)
C5	0.4376 (2)	0.13060 (12)	0.18557 (5)	0.0187 (3)
C6	0.4220 (2)	0.07070 (13)	0.22423 (5)	0.0214 (3)
N2	0.79571 (17)	0.31410 (9)	0.08449 (4)	0.0151 (2)
C7	0.7094 (2)	0.42076 (11)	0.08501 (5)	0.0192 (3)
C8	0.6060 (2)	0.44251 (13)	0.04323 (6)	0.0239 (3)
C9	0.8950 (2)	0.29787 (13)	0.12722 (5)	0.0212 (3)
C10	0.9187 (2)	0.18278 (14)	0.13903 (6)	0.0242 (3)
C11	0.9015 (2)	0.29386 (12)	0.04305 (5)	0.0166 (3)
C12	1.0456 (2)	0.37245 (13)	0.03620 (5)	0.0206 (3)
H2A	0.195 (3)	−0.1264 (16)	0.1819 (6)	0.023 (5)*
H3A	0.215 (3)	−0.0242 (14)	0.1159 (6)	0.021 (5)*
H5A	0.498 (3)	0.2009 (16)	0.1862 (6)	0.022 (5)*
H6A	0.471 (3)	0.0962 (17)	0.2514 (7)	0.035 (6)*
H7A	0.641 (3)	0.4184 (16)	0.1120 (7)	0.027 (5)*
H7B	0.807 (3)	0.4712 (16)	0.0893 (6)	0.020 (5)*
H8A	0.679 (3)	0.4491 (16)	0.0171 (6)	0.027 (5)*
H8B	0.517 (3)	0.3859 (17)	0.0374 (7)	0.028 (5)*
H8C	0.529 (3)	0.5072 (17)	0.0482 (7)	0.028 (5)*
H9A	1.007 (3)	0.3338 (14)	0.1233 (6)	0.020 (5)*
H9B	0.830 (3)	0.3364 (16)	0.1497 (7)	0.027 (5)*
H10A	0.981 (3)	0.1804 (17)	0.1669 (8)	0.039 (6)*
H10B	0.989 (3)	0.1457 (18)	0.1178 (7)	0.036 (6)*
H10C	0.817 (4)	0.147 (2)	0.1432 (7)	0.042 (6)*
H11A	0.825 (3)	0.2928 (14)	0.0187 (6)	0.014 (4)*
H11B	0.954 (3)	0.2213 (15)	0.0474 (6)	0.016 (4)*
H12A	1.143 (3)	0.3620 (15)	0.0569 (6)	0.021 (5)*
H12B	1.008 (3)	0.4425 (17)	0.0365 (6)	0.026 (5)*
H12C	1.100 (3)	0.3593 (19)	0.0071 (8)	0.036 (6)*
H1N2	0.702 (3)	0.2662 (15)	0.0832 (6)	0.017 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01496 (15)	0.01173 (14)	0.01322 (16)	0.00071 (12)	−0.00004 (11)	0.00010 (10)
O1	0.0965 (15)	0.0357 (8)	0.0251 (7)	−0.0290 (9)	−0.0008 (8)	0.0093 (5)
O2	0.0421 (8)	0.0529 (9)	0.0166 (6)	−0.0118 (7)	−0.0060 (5)	0.0093 (5)
O3	0.0202 (5)	0.0233 (5)	0.0152 (5)	−0.0025 (4)	−0.0050 (4)	0.0020 (4)
O4	0.0169 (5)	0.0156 (4)	0.0191 (5)	0.0004 (4)	0.0036 (4)	−0.0003 (4)
O5	0.0293 (6)	0.0124 (4)	0.0199 (5)	0.0041 (4)	0.0022 (4)	−0.0009 (4)
N1	0.0325 (8)	0.0300 (7)	0.0170 (6)	−0.0024 (6)	0.0024 (6)	0.0060 (5)
C1	0.0217 (7)	0.0208 (6)	0.0127 (6)	0.0010 (6)	0.0023 (5)	0.0034 (5)
C2	0.0213 (7)	0.0147 (6)	0.0163 (6)	−0.0011 (6)	0.0024 (5)	−0.0002 (5)
C3	0.0182 (6)	0.0154 (6)	0.0135 (6)	0.0005 (5)	0.0006 (5)	−0.0010 (4)
C4	0.0138 (6)	0.0139 (5)	0.0126 (6)	0.0020 (5)	0.0004 (5)	−0.0007 (4)
C5	0.0218 (7)	0.0177 (6)	0.0165 (7)	−0.0038 (6)	−0.0013 (5)	−0.0013 (5)
C6	0.0248 (8)	0.0255 (7)	0.0139 (6)	−0.0031 (6)	−0.0035 (6)	−0.0012 (5)
N2	0.0185 (6)	0.0132 (5)	0.0136 (5)	−0.0021 (5)	0.0002 (4)	0.0006 (4)
C7	0.0242 (7)	0.0130 (6)	0.0203 (7)	0.0007 (6)	0.0035 (6)	−0.0009 (5)
C8	0.0271 (8)	0.0218 (7)	0.0229 (8)	0.0061 (7)	0.0008 (6)	0.0042 (6)
C9	0.0294 (8)	0.0224 (7)	0.0119 (6)	−0.0032 (6)	−0.0020 (6)	0.0014 (5)
C10	0.0215 (8)	0.0275 (8)	0.0234 (8)	0.0041 (7)	−0.0023 (6)	0.0059 (6)
C11	0.0215 (7)	0.0165 (6)	0.0117 (6)	0.0018 (6)	0.0004 (5)	−0.0013 (5)
C12	0.0199 (7)	0.0234 (7)	0.0183 (7)	−0.0008 (6)	0.0025 (6)	0.0018 (5)

Geometric parameters (Å, º) top

S1—O3	1.4468 (11)	N2—H1N2	0.95 (2)
S1—O5	1.4531 (11)	C7—C8	1.513 (2)
S1—O4	1.4709 (11)	C7—H7A	0.97 (2)
S1—C4	1.7865 (14)	C7—H7B	1.00 (2)
O1—N1	1.226 (2)	C8—H8A	0.97 (2)
O2—N1	1.2233 (19)	C8—H8B	1.01 (2)
N1—C1	1.4738 (19)	C8—H8C	1.03 (2)
C1—C2	1.386 (2)	C9—C10	1.512 (2)
C1—C6	1.391 (2)	C9—H9A	0.99 (2)
C2—C3	1.394 (2)	C9—H9B	0.97 (2)
C2—H2A	0.96 (2)	C10—H10A	0.97 (2)
C3—C4	1.387 (2)	C10—H10B	0.96 (2)
C3—H3A	1.015 (19)	C10—H10C	0.92 (3)
C4—C5	1.402 (2)	C11—C12	1.516 (2)
C5—C6	1.388 (2)	C11—H11A	0.943 (18)
C5—H5A	1.01 (2)	C11—H11B	1.014 (19)
C6—H6A	0.96 (2)	C12—H12A	0.99 (2)
N2—C9	1.5087 (19)	C12—H12B	0.93 (2)
N2—C7	1.5101 (19)	C12—H12C	0.98 (2)
N2—C11	1.5110 (19)

O3—S1—O5	115.07 (7)	C8—C7—H7A	113.7 (13)
O3—S1—O4	113.04 (7)	N2—C7—H7B	103.5 (12)
O5—S1—O4	111.77 (7)	C8—C7—H7B	113.2 (11)
O3—S1—C4	106.18 (6)	H7A—C7—H7B	109.3 (16)
O5—S1—C4	105.13 (6)	C7—C8—H8A	111.7 (13)
O4—S1—C4	104.57 (6)	C7—C8—H8B	112.2 (11)
O2—N1—O1	123.45 (14)	H8A—C8—H8B	108.7 (16)
O2—N1—C1	118.27 (14)	C7—C8—H8C	109.8 (11)
O1—N1—C1	118.28 (14)	H8A—C8—H8C	113.0 (16)
C2—C1—C6	123.21 (13)	H8B—C8—H8C	101.0 (17)
C2—C1—N1	118.25 (14)	N2—C9—C10	113.09 (13)
C6—C1—N1	118.53 (13)	N2—C9—H9A	106.9 (11)
C1—C2—C3	117.81 (14)	C10—C9—H9A	111.2 (11)
C1—C2—H2A	121.8 (11)	N2—C9—H9B	104.5 (13)
C3—C2—H2A	120.3 (11)	C10—C9—H9B	112.7 (12)
C4—C3—C2	120.31 (13)	H9A—C9—H9B	108.0 (16)
C4—C3—H3A	120.9 (11)	C9—C10—H10A	107.0 (13)
C2—C3—H3A	118.6 (11)	C9—C10—H10B	112.8 (13)
C3—C4—C5	120.74 (13)	H10A—C10—H10B	106 (2)
C3—C4—S1	119.83 (10)	C9—C10—H10C	113.7 (16)
C5—C4—S1	119.42 (11)	H10A—C10—H10C	107.5 (19)
C6—C5—C4	119.75 (14)	H10B—C10—H10C	110 (2)
C6—C5—H5A	120.6 (10)	N2—C11—C12	113.86 (12)
C4—C5—H5A	119.6 (10)	N2—C11—H11A	106.8 (11)
C5—C6—C1	118.18 (14)	C12—C11—H11A	112.1 (11)
C5—C6—H6A	119.3 (14)	N2—C11—H11B	105.6 (10)
C1—C6—H6A	122.6 (14)	C12—C11—H11B	108.3 (11)
C9—N2—C7	110.01 (12)	H11A—C11—H11B	109.9 (15)
C9—N2—C11	113.05 (12)	C11—C12—H12A	113.4 (11)
C7—N2—C11	113.83 (11)	C11—C12—H12B	113.1 (13)
C9—N2—H1N2	110.1 (11)	H12A—C12—H12B	111.1 (17)
C7—N2—H1N2	103.1 (11)	C11—C12—H12C	109.2 (14)
C11—N2—H1N2	106.2 (11)	H12A—C12—H12C	101.6 (17)
N2—C7—C8	113.10 (12)	H12B—C12—H12C	107.7 (18)
N2—C7—H7A	103.1 (12)

O2—N1—C1—C2	−176.81 (16)	O5—S1—C4—C5	−38.73 (14)
O1—N1—C1—C2	2.8 (2)	O4—S1—C4—C5	79.13 (13)
O2—N1—C1—C6	3.1 (2)	C3—C4—C5—C6	−0.4 (2)
O1—N1—C1—C6	−177.33 (18)	S1—C4—C5—C6	−179.65 (12)
C6—C1—C2—C3	−0.9 (2)	C4—C5—C6—C1	0.3 (2)
N1—C1—C2—C3	178.93 (14)	C2—C1—C6—C5	0.4 (3)
C1—C2—C3—C4	0.8 (2)	N1—C1—C6—C5	−179.46 (15)
C2—C3—C4—C5	−0.1 (2)	C9—N2—C7—C8	−179.61 (14)
C2—C3—C4—S1	179.10 (11)	C11—N2—C7—C8	52.33 (18)
O3—S1—C4—C3	19.67 (13)	C7—N2—C9—C10	154.66 (14)
O5—S1—C4—C3	142.05 (12)	C11—N2—C9—C10	−76.86 (17)
O4—S1—C4—C3	−100.09 (12)	C9—N2—C11—C12	−66.52 (16)
O3—S1—C4—C5	−161.10 (12)	C7—N2—C11—C12	59.96 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O4	0.95 (2)	1.86 (2)	2.7899 (17)	166 (2)
C2—H2A···O5ⁱ	0.96 (2)	2.485 (19)	3.1000 (19)	121.7 (14)
C7—H7B···O4ⁱⁱ	1.00 (2)	2.50 (2)	3.4081 (19)	151.3 (16)
C10—H10B···O3ⁱⁱⁱ	0.96 (2)	2.59 (2)	3.461 (2)	151.1 (18)
C12—H12A···O5ⁱⁱⁱ	0.99 (2)	2.60 (2)	3.559 (2)	164.1 (16)

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

Experimental details

Crystal data
Chemical formula	C₆H₁₆N⁺·C₆H₄NO₅S⁻
M_r	304.36
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	7.8015 (14), 12.669 (2), 29.910 (6)
V (Å³)	2956.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.18 × 0.14

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.950, 0.967
No. of measured, independent and observed [I > 2σ(I)] reflections	21787, 5605, 3985
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.771

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.01
No. of reflections	5605
No. of parameters	261
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.47

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
N2—H1N2···O4	0.95 (2)	1.86 (2)	2.7899 (17)	166 (2)
C2—H2A···O5ⁱ	0.96 (2)	2.485 (19)	3.1000 (19)	121.7 (14)
C7—H7B···O4ⁱⁱ	1.00 (2)	2.50 (2)	3.4081 (19)	151.3 (16)
C10—H10B···O3ⁱⁱⁱ	0.96 (2)	2.59 (2)	3.461 (2)	151.1 (18)
C12—H12A···O5ⁱⁱⁱ	0.99 (2)	2.60 (2)	3.559 (2)	164.1 (16)

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

Footnotes

‡Additional correspondence author, e-mail: nornisah@usm.my.

§Thomson Reuters ResearcherID: A-5525-2009.

¶Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The authors gratefully acknowledge funding from Universiti Sains Malaysia (USM) under the University Research Grant (No. 1001/PFARMASI/815025). HKF and CKQ thank USM for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ also thanks USM for the award of a USM Fellowship.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Dann, A. T. & Davies, W. (1929). J. Chem. Soc. pp. 1050–1058. CrossRef Google Scholar
D'Souza, M. J., Yaakoubd, S. L. & Kevill, D. N. (2008). Int. J. Mol. Sci. 9, 914–925. Web of Science PubMed CAS Google Scholar
Hunig, S., Muller, H. R. & Their, W. (1965). Angew. Chem. Int. Ed. Engl. 4, 271–279. CrossRef Web of Science Google Scholar
Kim, Y. H., Jung, J. C., Choi, H. C. & Yang, S. G. (1999). Pure Appl. Chem. 71, 377–384. Web of Science CrossRef CAS Google Scholar
Quah, C. K., Jebas, S. R. & Fun, H.-K. (2008). Acta Cryst. E64, o1878–o1879. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar