(E)-N′-(4-Bromo­benzyl­idene)-p-toluene­sulfonohydrazide

Kia, R.; Etemadi, B.; Fun, H.-K.; Kargar, H.

doi:10.1107/S1600536809009751

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Pages o821-o822

doi:10.1107/S1600536809009751

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(E)-N′-(4-Bromobenzylidene)-p-toluenesulfonohydrazide

Reza Kia,^a Bijan Etemadi,^b Hoong-Kun Fun ^a ^* and Hadi Kargar ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Earth Sciences, College of Sciences, Shiraz University, Shiraz, Iran, and ^cDepartment of Chemistry, School of Science, Payame Noor University (PNU), Ardakan, Yazd, Iran
^*Correspondence e-mail: hkfun@usm.my

(Received 5 March 2009; accepted 17 March 2009; online 25 March 2009)

In the title compound, C₁₄H₁₃BrN₂O₂S, a novel sulfonamide derivative, intermolecular N—H⋯O and C—H⋯O hydrogen bonds link neighbouring molecules into different dimers along the b axis, generating R₂²(8) and R₂²(16) ring motifs. The dihedral angle between the benzene rings is 82.39 (13)°. The crystal structure is further stabilized by intermolecular π–π stacking interactions [centroid–centroid distances = 3.867 (2)–3.9548 (8) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For related structures and applications, see, for example: Kia et al. (2008a ,b ); Tabatabaee et al. (2007 ); Ali et al. (2007 ); Tierney et al. 2006 ; Krygowski et al. (1998 ); Mehrabi et al. (2008 ); Kayser et al. (2004 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₄H₁₃BrN₂O₂S
M_r = 353.23
Triclinic, $[P \overline 1]$
a = 5.9565 (3) Å
b = 9.4005 (3) Å
c = 12.8020 (6) Å
α = 97.153 (2)°
β = 96.350 (2)°
γ = 92.125 (1)°
V = 705.95 (5) Å³
Z = 2
Mo Kα radiation
μ = 3.06 mm⁻¹
T = 100 K
0.57 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.276, T_max = 0.819
18030 measured reflections
5040 independent reflections
4098 reflections with I > 2˘I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.106
S = 1.11
5040 reflections
187 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A⋯O1ⁱⁱ	0.98	2.57	3.420 (3)	145
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809009751/rz2299sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009751/rz2299Isup2.hkl

checkCIF report

Comment top

Sulfonamides were the first class of antimicrobial agents to be discovered. They inhibit dihydropteroate synthetase in the bacterial folic acid pathway. Although their clinical role has diminished, they are still useful in certain situations, because of its efficacy and low cost (Krygowski et al., 1998). Sulfonamides (sulfanilamide, sulfamethoxazole, sulfafurazole) are structural analogues of p-aminobenzoic acid (PABA) and compete with PABA to block its conversion to dihydrofolic acid. These agents are generally used in combination with other drugs (usually sulfonamides) to prevent or treat a number of bacterial and parasitic infections (Tierney et al., 2006). Because of the above impotrtant features, we report the crystal structure of the title compound.

The title compund (Fig. 1), is a novel sulfonamide derivative. Bond lengths (Allen et al., 1987) and angles are within the normal ranges and are comparable with the related staructures (Kia et al. 2008a,b; Mehrabi et al., 2008; Ali et al. 2007). Intermolecular N—H···O and C—H···O hydrogen bonds link neighbouring molecules by R₂²(8) and R₂²(16) ring motifs (Bernstein et al., 1995), respectively, into different dimers along the b axis. The dihedral angle between the two benzene rings is 82.39 (13)°. The crystal structure is further stabilized by intermolecular π-π stacking interactions [Cg1···Cg1 ⁱⁱⁱ = 3.9319 (15) and Cg2···Cg2^iv = 3.8677 (16) Å; the perpendicular distances are 3.6548 (10) and 3.6189 (11) Å, respectively. Symmetry codes: (iii) -x, 2 - y, 1 - z; (iv) 2 - x, 1 - y, 2 - z].

Related literature top

For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995). For related structures and applications, see, for example: Kia et al. (2008a,b); Tabatabaee et al. (2007); Ali et al. (2007); Tierney et al. 2006; Krygowski et al. (1998); Mehrabi et al. (2008). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For related literature, see: Kayser et al. (2004).

Experimental top

p-Tosylhydrazine (2 mmol) was added to a 50 ml refluxing ethanolic solution of 4-bromobenzaldehyde (2 mmol). The mixture was stirred for 2 h. After cooling, the colorless crystalline solid was isolated by filtration, washed with cold ethanol, and re-crystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed down the a axis, showing linking of different dimers along the b axis through N—H···O and C—H···O interactions. Intermolecular hydrogen bonds are shown as dashed lines.

(E)-N'-(4-Bromobenzylidene)-p-toluenesulfonohydrazide top

Crystal data top

C₁₄H₁₃BrN₂O₂S	Z = 2
M_r = 353.23	F(000) = 356
Triclinic, P1	D_x = 1.662 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9565 (3) Å	Cell parameters from 7222 reflections
b = 9.4005 (3) Å	θ = 2.5–34.1°
c = 12.8020 (6) Å	µ = 3.06 mm⁻¹
α = 97.153 (2)°	T = 100 K
β = 96.350 (2)°	Block, colourless
γ = 92.125 (1)°	0.57 × 0.15 × 0.07 mm
V = 705.95 (5) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5040 independent reflections
Radiation source: fine-focus sealed tube	4098 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 32.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→8
T_min = 0.276, T_max = 0.819	k = −14→14
18030 measured reflections	l = −18→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0387P)² + 1.0631P] where P = (F_o² + 2F_c²)/3
5040 reflections	(Δ/σ)_max < 0.001
187 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₄H₁₃BrN₂O₂S	γ = 92.125 (1)°
M_r = 353.23	V = 705.95 (5) Å³
Triclinic, P1	Z = 2
a = 5.9565 (3) Å	Mo Kα radiation
b = 9.4005 (3) Å	µ = 3.06 mm⁻¹
c = 12.8020 (6) Å	T = 100 K
α = 97.153 (2)°	0.57 × 0.15 × 0.07 mm
β = 96.350 (2)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5040 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4098 reflections with I > 2˘I)
T_min = 0.276, T_max = 0.819	R_int = 0.034
18030 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.63 e Å⁻³
5040 reflections	Δρ_min = −0.56 e Å⁻³
187 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
Br1	0.81285 (5)	0.24366 (3)	−0.11229 (2)	0.02400 (8)
S1	0.25512 (10)	0.69735 (6)	0.50609 (4)	0.01269 (11)
O1	0.1164 (3)	0.66003 (19)	0.58555 (14)	0.0166 (3)
O2	0.4777 (3)	0.76093 (19)	0.53840 (15)	0.0171 (3)
N1	0.2703 (4)	0.5426 (2)	0.43423 (17)	0.0147 (4)
N2	0.3865 (4)	0.5374 (2)	0.34562 (16)	0.0149 (4)
C1	−0.1178 (4)	0.7666 (3)	0.3846 (2)	0.0162 (4)
H1A	−0.1895	0.6830	0.4034	0.019*
C2	−0.2334 (4)	0.8507 (3)	0.3168 (2)	0.0187 (5)
H2A	−0.3851	0.8231	0.2884	0.022*
C3	−0.1313 (5)	0.9747 (3)	0.2894 (2)	0.0179 (5)
C4	0.0912 (5)	1.0145 (3)	0.3328 (2)	0.0194 (5)
H4A	0.1614	1.1000	0.3162	0.023*
C5	0.2112 (4)	0.9315 (3)	0.3994 (2)	0.0162 (4)
H5A	0.3632	0.9587	0.4275	0.019*
C6	0.1059 (4)	0.8075 (2)	0.42462 (19)	0.0139 (4)
C7	0.3238 (4)	0.4296 (3)	0.2753 (2)	0.0159 (4)
H7A	0.1980	0.3695	0.2850	0.019*
C8	0.4385 (4)	0.3958 (3)	0.18089 (19)	0.0156 (4)
C9	0.3420 (5)	0.2868 (3)	0.1030 (2)	0.0190 (5)
H9A	0.2005	0.2417	0.1106	0.023*
C10	0.4502 (5)	0.2435 (3)	0.0144 (2)	0.0208 (5)
H10A	0.3833	0.1699	−0.0387	0.025*
C11	0.6578 (4)	0.3098 (3)	0.0051 (2)	0.0176 (5)
C12	0.7559 (5)	0.4195 (3)	0.0805 (2)	0.0196 (5)
H12A	0.8971	0.4646	0.0722	0.023*
C13	0.6460 (5)	0.4627 (3)	0.1682 (2)	0.0180 (5)
H13A	0.7119	0.5381	0.2200	0.022*
C14	−0.2579 (5)	1.0639 (3)	0.2146 (2)	0.0255 (6)
H14A	−0.2504	1.1643	0.2471	0.038*
H14B	−0.4164	1.0282	0.2000	0.038*
H14C	−0.1893	1.0572	0.1481	0.038*
H1N1	0.160 (6)	0.483 (4)	0.436 (3)	0.020 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.02205 (14)	0.03319 (15)	0.01596 (12)	0.00426 (11)	0.00449 (10)	−0.00286 (10)
S1	0.0128 (3)	0.0121 (2)	0.0130 (2)	−0.00060 (19)	0.0009 (2)	0.00153 (18)
O1	0.0189 (9)	0.0168 (8)	0.0144 (8)	−0.0017 (7)	0.0046 (7)	0.0014 (6)
O2	0.0138 (8)	0.0154 (8)	0.0213 (9)	−0.0018 (6)	−0.0020 (7)	0.0039 (6)
N1	0.0160 (10)	0.0117 (8)	0.0167 (9)	−0.0009 (7)	0.0047 (8)	0.0009 (7)
N2	0.0151 (10)	0.0159 (9)	0.0141 (9)	0.0022 (7)	0.0030 (7)	0.0020 (7)
C1	0.0137 (11)	0.0157 (10)	0.0186 (11)	−0.0015 (8)	0.0005 (9)	0.0017 (8)
C2	0.0155 (11)	0.0206 (11)	0.0190 (11)	0.0027 (9)	−0.0012 (9)	0.0010 (9)
C3	0.0232 (13)	0.0135 (10)	0.0158 (10)	0.0046 (9)	−0.0007 (9)	−0.0011 (8)
C4	0.0237 (13)	0.0123 (10)	0.0219 (12)	0.0007 (9)	0.0014 (10)	0.0027 (9)
C5	0.0166 (11)	0.0138 (10)	0.0174 (11)	−0.0009 (8)	0.0007 (9)	0.0006 (8)
C6	0.0150 (10)	0.0131 (9)	0.0136 (10)	0.0004 (8)	0.0020 (8)	0.0017 (8)
C7	0.0154 (11)	0.0151 (10)	0.0178 (11)	0.0011 (8)	0.0029 (9)	0.0031 (8)
C8	0.0159 (11)	0.0159 (10)	0.0154 (10)	0.0034 (8)	0.0011 (9)	0.0036 (8)
C9	0.0168 (12)	0.0195 (11)	0.0202 (12)	0.0015 (9)	0.0013 (9)	0.0007 (9)
C10	0.0207 (13)	0.0228 (12)	0.0169 (11)	0.0010 (10)	0.0005 (10)	−0.0033 (9)
C11	0.0175 (11)	0.0214 (11)	0.0142 (10)	0.0045 (9)	0.0022 (9)	0.0023 (9)
C12	0.0188 (12)	0.0212 (11)	0.0197 (12)	0.0010 (9)	0.0055 (10)	0.0037 (9)
C13	0.0195 (12)	0.0170 (11)	0.0172 (11)	−0.0014 (9)	0.0028 (9)	0.0008 (9)
C14	0.0335 (16)	0.0178 (11)	0.0226 (13)	0.0073 (11)	−0.0081 (11)	0.0010 (9)

Geometric parameters (Å, º) top

Br1—C11	1.901 (2)	C5—C6	1.393 (3)
S1—O2	1.4297 (19)	C5—H5A	0.9500
S1—O1	1.4469 (18)	C7—C8	1.460 (3)
S1—N1	1.633 (2)	C7—H7A	0.9500
S1—C6	1.756 (2)	C8—C9	1.396 (4)
N1—N2	1.389 (3)	C8—C13	1.400 (4)
N1—H1N1	0.85 (3)	C9—C10	1.390 (4)
N2—C7	1.283 (3)	C9—H9A	0.9500
C1—C2	1.390 (3)	C10—C11	1.388 (4)
C1—C6	1.395 (3)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.385 (4)
C2—C3	1.396 (4)	C12—C13	1.387 (4)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.398 (4)	C13—H13A	0.9500
C3—C14	1.509 (4)	C14—H14A	0.9800
C4—C5	1.386 (4)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800

O2—S1—O1	119.47 (11)	N2—C7—C8	122.5 (2)
O2—S1—N1	109.68 (11)	N2—C7—H7A	118.8
O1—S1—N1	102.07 (11)	C8—C7—H7A	118.8
O2—S1—C6	108.68 (11)	C9—C8—C13	119.0 (2)
O1—S1—C6	109.36 (11)	C9—C8—C7	118.2 (2)
N1—S1—C6	106.81 (11)	C13—C8—C7	122.7 (2)
N2—N1—S1	118.59 (16)	C10—C9—C8	120.9 (2)
N2—N1—H1N1	120 (2)	C10—C9—H9A	119.5
S1—N1—H1N1	114 (2)	C8—C9—H9A	119.5
C7—N2—N1	113.5 (2)	C11—C10—C9	118.7 (2)
C2—C1—C6	118.6 (2)	C11—C10—H10A	120.6
C2—C1—H1A	120.7	C9—C10—H10A	120.6
C6—C1—H1A	120.7	C12—C11—C10	121.6 (2)
C1—C2—C3	121.4 (2)	C12—C11—Br1	119.75 (19)
C1—C2—H2A	119.3	C10—C11—Br1	118.67 (19)
C3—C2—H2A	119.3	C11—C12—C13	119.3 (2)
C2—C3—C4	118.5 (2)	C11—C12—H12A	120.4
C2—C3—C14	120.8 (2)	C13—C12—H12A	120.4
C4—C3—C14	120.6 (2)	C12—C13—C8	120.5 (2)
C5—C4—C3	121.2 (2)	C12—C13—H13A	119.8
C5—C4—H4A	119.4	C8—C13—H13A	119.8
C3—C4—H4A	119.4	C3—C14—H14A	109.5
C4—C5—C6	119.1 (2)	C3—C14—H14B	109.5
C4—C5—H5A	120.5	H14A—C14—H14B	109.5
C6—C5—H5A	120.5	C3—C14—H14C	109.5
C5—C6—C1	121.2 (2)	H14A—C14—H14C	109.5
C5—C6—S1	120.30 (19)	H14B—C14—H14C	109.5
C1—C6—S1	118.52 (18)

O2—S1—N1—N2	−54.7 (2)	O2—S1—C6—C1	−179.30 (19)
O1—S1—N1—N2	177.61 (18)	O1—S1—C6—C1	−47.3 (2)
C6—S1—N1—N2	62.9 (2)	N1—S1—C6—C1	62.4 (2)
S1—N1—N2—C7	−156.20 (19)	N1—N2—C7—C8	−173.9 (2)
C6—C1—C2—C3	−0.8 (4)	N2—C7—C8—C9	−172.5 (2)
C1—C2—C3—C4	−0.6 (4)	N2—C7—C8—C13	10.9 (4)
C1—C2—C3—C14	179.2 (2)	C13—C8—C9—C10	0.7 (4)
C2—C3—C4—C5	1.6 (4)	C7—C8—C9—C10	−176.0 (2)
C14—C3—C4—C5	−178.3 (2)	C8—C9—C10—C11	0.6 (4)
C3—C4—C5—C6	−1.0 (4)	C9—C10—C11—C12	−1.5 (4)
C4—C5—C6—C1	−0.5 (4)	C9—C10—C11—Br1	176.8 (2)
C4—C5—C6—S1	178.40 (19)	C10—C11—C12—C13	1.0 (4)
C2—C1—C6—C5	1.4 (4)	Br1—C11—C12—C13	−177.21 (19)
C2—C1—C6—S1	−177.52 (19)	C11—C12—C13—C8	0.3 (4)
O2—S1—C6—C5	1.8 (2)	C9—C8—C13—C12	−1.2 (4)
O1—S1—C6—C5	133.8 (2)	C7—C8—C13—C12	175.4 (2)
N1—S1—C6—C5	−116.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A···O1ⁱⁱ	0.98	2.57	3.420 (3)	145

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃BrN₂O₂S
M_r	353.23
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.9565 (3), 9.4005 (3), 12.8020 (6)
α, β, γ (°)	97.153 (2), 96.350 (2), 92.125 (1)
V (Å³)	705.95 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.06
Crystal size (mm)	0.57 × 0.15 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.276, 0.819
No. of measured, independent and observed [I > 2˘I)] reflections	18030, 5040, 4098
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.756

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.106, 1.11
No. of reflections	5040
No. of parameters	187
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.56

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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···O1ⁱ	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A···O1ⁱⁱ	0.9800	2.5700	3.420 (3)	145.00

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

Acknowledgements

HKF and RK thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship. BE thanks Shiraz University for financial support. HK thanks PNU for financial support. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). 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
Kayser, F. H., Bienz, K. A., Eckert, J. & Zinkernagel, R. M. (2004). Medical Microbiology, pp. 1–20. Berlin: Thieme Medical. Google Scholar
Kia, R., Fun, H.-K. & Kargar, H. (2008a). Acta Cryst. E64, o2341. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kia, R., Fun, H.-K. & Kargar, H. (2008b). Acta Cryst. E64, o2424. Web of Science CSD CrossRef IUCr Journals Google Scholar
Krygowski, T. M., Pietka, E., Anulewicz, R., Cyranski, M. K. & Nowacki, J. (1998). Tetrahedron, 54, 12289–12292. Web of Science CSD CrossRef CAS Google Scholar
Mehrabi, H., Kia, R., Hassanzadeh, A., Ghobadi, S. & Khavasi, H. R. (2008). Acta Cryst. E64, o1845. Web of Science CSD CrossRef 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
Tabatabaee, M., Anari-Abbasnejad, M., Nozari, N., Sadegheian, S. & Ghasemzadeh, M. (2007). Acta Cryst. E63, o2099–o2100. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tierney, M. S. Jr, McPhee, J. & Papadakis, M. A. (2006). Current Medical Diagnosis & Treatment, 45th ed., pp. 1–50. New York: McGraw–Hill Medical. Google Scholar