N-(3-Chloro­phen­yl)-1,2-benzisothia­zol-3-amine 1,1-dioxide

Shah, T.S.; Siddiqui, W.A.; Tahir, M.N.; Hussain, G.

doi:10.1107/S1600536810015163

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1220

https://doi.org/10.1107/S1600536810015163

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N-(3-Chlorophenyl)-1,2-benzisothiazol-3-amine 1,1-dioxide

Tariq Saeed Shah,^a Waseeq Ahmad Siddiqui,^a M. Nawaz Tahir ^b ^* and Ghulam Hussain ^a

^aDepartment of Chemistry, University of Sargodha, Sargodha, Pakistan, and ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 31 March 2010; accepted 25 April 2010; online 30 April 2010)

In the title compound, C₁₃H₉ClN₂O₂S, the dihedral angle between the aromatic ring systems is 6.00 (12)° and an intramolecular C—H⋯N interaction generates an S(6) ring. In the crystal, molecules interact by way of C—H⋯O and N—H⋯O bonds, generating R₂¹(7) and R₂²(10) ring motifs, and aromatic π–π stacking interactions [centroid–centroid separations = 3.730 (3) and 3.733 (2) Å] help to consolidate the packing.

Related literature

For other saccharin derivatives, see: Rafique et al. (2009 ); Siddiqui et al. (2010 ). For a related structure, see: Brigas et al. (2001 ). For graph-set theory, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₉ClN₂O₂S
M_r = 292.73
Triclinic, $[P \overline 1]$
a = 7.2223 (10) Å
b = 7.9138 (12) Å
c = 11.2175 (17) Å
α = 96.178 (6)°
β = 98.840 (5)°
γ = 97.574 (5)°
V = 622.63 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.47 mm⁻¹
T = 296 K
0.28 × 0.10 × 0.08 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.947, T_max = 0.962
10481 measured reflections
2700 independent reflections
1244 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.115
S = 0.98
2700 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯N2	0.93	2.28	2.901 (5)	124
N1—H1⋯O1ⁱ	0.86	2.24	3.084 (4)	165
C5—H5⋯O1ⁱ	0.93	2.51	3.396 (4)	159
C2—H2⋯O2ⁱⁱ	0.93	2.42	3.302 (4)	158
Symmetry codes: (i) x-1, y, z; (ii) -x+3, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810015163/hb5389sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015163/hb5389Isup2.hkl

checkCIF report

Comment top

Due to the interest in obtaining new derivatives of saccharin (Rafique et al., 2009: Siddiqui et al., 2010), we wish to report the preparation and crystal structure of the title compound (I, Fig. 1).

The crystal structure of (II) N-(1,1-Dioxo-1,2-benzisothiazol-3-yl)-4- methoxyaniline (Brigas et al., 2001) and (III) N-(1,1-Dioxo-1,2-benzisothiazol-3-yl)-3-methylaniline (Brigas et al., 2001) have been published. The title compound differs from (II) and (III) due to attachement of chloro substition on the aniline. In (I), 1,2-benzisothiazol-3-amine A (C–C7/N2/S1) and 3-Chlorophenyl B (C8–C13/CL1) are planar with maximum r. m. s. deviations of 0.0080 Å and 0.0033 Å from the respective mean square planes. The dihedral angle between A/B is 6.00 (12)°. There exists an intramolecular H-bonding of C–H···N type forming S(6) ring motif (Bernstein et al., 1995). The molecules are stabilized in the form of polymeric sheets due to intermolecular H-bondings (Table 1, Fig. 2) completing R₂¹(7) and R₂²(10) ring motifs. There exist π–π interactions at a distance of 3.733 (2) Å and 3.730 (2) Å, between the centroids of the benzene rings Cg1 (C1—C6) and Cg2 (C8—C13) respectively, [Cg1···Cg1ⁱ: i = 2 - x,-y, 1 - z] and [Cg2···Cg2ⁱⁱ: ii = 1 - x,-y, - z].

Related literature top

For other saccharin derivatives, see: Rafique et al. (2009); Siddiqui et al. (2010). For a related structure, see: Brigas et al. (2001). For graph-set theory, see: Bernstein et al. (1995);

Experimental top

A mixture of saccharin (1.0 g, 5.46 mmol) and m-chloroaniline (5 ml, in excess) was heated to reflux on an oil-bath (4 h), cooled to room temperature and kept overnight in a freezer. The solvent was evaporated under reduced pressure and the brownish yellow paste obtained was washed with benzene (4 × 25 ml) to obtain the bright light brown crystalline product (1.25, 78%, m. p. 578-579 K). Recrystallisation solvent: MeOH:AcOEt (1:1): the solution was subjected to slow evaporation at room temperature to obtain colourless needles of (I).

Structure description top

For other saccharin derivatives, see: Rafique et al. (2009); Siddiqui et al. (2010). For a related structure, see: Brigas et al. (2001). For graph-set theory, see: Bernstein et al. (1995);

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing of (I), which shows that molecules form polymeric sheets with various ring motifs.

N-(3-Chlorophenyl)-1,2-benzisothiazol-3-amine 1,1-dioxide top

Crystal data top

C₁₃H₉ClN₂O₂S	Z = 2
M_r = 292.73	F(000) = 300
Triclinic, P1	D_x = 1.561 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2223 (10) Å	Cell parameters from 1244 reflections
b = 7.9138 (12) Å	θ = 2.6–27.1°
c = 11.2175 (17) Å	µ = 0.47 mm⁻¹
α = 96.178 (6)°	T = 296 K
β = 98.840 (5)°	Needle, colourless
γ = 97.574 (5)°	0.28 × 0.10 × 0.08 mm
V = 622.63 (16) Å³

Data collection top

Bruker Kappa APEXII CCD diffractometer	2700 independent reflections
Radiation source: fine-focus sealed tube	1244 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
Detector resolution: 7.60 pixels mm^-1	θ_max = 27.1°, θ_min = 2.6°
ω scans	h = −8→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
T_min = 0.947, T_max = 0.962	l = −14→14
10481 measured reflections

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0363P)²] where P = (F_o² + 2F_c²)/3
2700 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₃H₉ClN₂O₂S	γ = 97.574 (5)°
M_r = 292.73	V = 622.63 (16) Å³
Triclinic, P1	Z = 2
a = 7.2223 (10) Å	Mo Kα radiation
b = 7.9138 (12) Å	µ = 0.47 mm⁻¹
c = 11.2175 (17) Å	T = 296 K
α = 96.178 (6)°	0.28 × 0.10 × 0.08 mm
β = 98.840 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2700 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1244 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.962	R_int = 0.088
10481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 0.98	Δρ_max = 0.25 e Å⁻³
2700 reflections	Δρ_min = −0.26 e Å⁻³
172 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	1.1663 (5)	0.2836 (4)	0.4969 (3)	0.0380 (9)
C2	1.2431 (5)	0.3741 (5)	0.6082 (3)	0.0512 (11)
H2	1.3719	0.4162	0.6278	0.061*
C3	1.1225 (6)	0.4010 (5)	0.6905 (3)	0.0566 (12)
H3	1.1705	0.4625	0.7668	0.068*
C4	0.9329 (6)	0.3379 (5)	0.6609 (4)	0.0557 (11)
H4	0.8542	0.3572	0.7177	0.067*
C5	0.8563 (5)	0.2460 (5)	0.5481 (3)	0.0466 (10)
H5	0.7275	0.2038	0.5289	0.056*
C6	0.9745 (5)	0.2185 (4)	0.4651 (3)	0.0352 (9)
C7	0.9368 (5)	0.1246 (4)	0.3407 (3)	0.0374 (9)
C8	0.6944 (4)	−0.0592 (4)	0.1789 (3)	0.0361 (9)
C9	0.5043 (5)	−0.1312 (5)	0.1558 (3)	0.0426 (10)
H9	0.4257	−0.1074	0.2119	0.051*
C10	0.4338 (5)	−0.2380 (5)	0.0491 (3)	0.0415 (10)
C11	0.5448 (5)	−0.2769 (5)	−0.0357 (3)	0.0482 (10)
H11	0.4944	−0.3497	−0.1073	0.058*
C12	0.7330 (5)	−0.2050 (5)	−0.0116 (3)	0.0485 (11)
H12	0.8109	−0.2302	−0.0677	0.058*
C13	0.8080 (5)	−0.0967 (5)	0.0939 (3)	0.0457 (10)
H13	0.9353	−0.0485	0.1081	0.055*
Cl1	0.19425 (13)	−0.32624 (14)	0.02129 (9)	0.0658 (4)
N1	0.7608 (4)	0.0472 (4)	0.2912 (3)	0.0417 (8)
H1	0.6751	0.0650	0.3345	0.050*
N2	1.0821 (4)	0.1190 (4)	0.2841 (3)	0.0428 (8)
O1	1.4055 (3)	0.1090 (3)	0.4010 (2)	0.0619 (8)
O2	1.3450 (4)	0.3710 (3)	0.3184 (2)	0.0645 (8)
S1	1.27387 (13)	0.22471 (14)	0.37119 (9)	0.0481 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.029 (2)	0.039 (2)	0.041 (2)	−0.0055 (17)	0.0023 (17)	0.0026 (19)
C2	0.044 (2)	0.052 (3)	0.047 (3)	−0.011 (2)	−0.003 (2)	−0.001 (2)
C3	0.062 (3)	0.062 (3)	0.039 (3)	−0.004 (2)	0.002 (2)	−0.002 (2)
C4	0.056 (3)	0.063 (3)	0.045 (3)	−0.001 (2)	0.013 (2)	−0.001 (2)
C5	0.036 (2)	0.059 (3)	0.041 (2)	−0.0003 (19)	0.0038 (19)	0.002 (2)
C6	0.033 (2)	0.039 (2)	0.033 (2)	0.0038 (17)	0.0032 (17)	0.0035 (19)
C7	0.028 (2)	0.037 (2)	0.043 (2)	−0.0002 (17)	0.0007 (17)	0.0000 (19)
C8	0.028 (2)	0.040 (2)	0.036 (2)	0.0022 (17)	0.0018 (17)	−0.0021 (19)
C9	0.030 (2)	0.048 (3)	0.047 (3)	−0.0001 (18)	0.0107 (18)	−0.005 (2)
C10	0.027 (2)	0.042 (3)	0.049 (3)	−0.0019 (17)	0.0015 (18)	−0.005 (2)
C11	0.040 (2)	0.054 (3)	0.044 (2)	−0.0013 (19)	0.0037 (19)	−0.010 (2)
C12	0.036 (2)	0.064 (3)	0.042 (2)	0.002 (2)	0.0083 (19)	−0.007 (2)
C13	0.024 (2)	0.065 (3)	0.044 (2)	0.0020 (18)	0.0045 (18)	0.001 (2)
Cl1	0.0325 (6)	0.0807 (9)	0.0706 (8)	−0.0122 (5)	0.0055 (5)	−0.0205 (6)
N1	0.0249 (16)	0.054 (2)	0.0411 (19)	−0.0042 (14)	0.0069 (14)	−0.0036 (16)
N2	0.0248 (16)	0.057 (2)	0.0421 (19)	−0.0024 (14)	0.0065 (14)	−0.0062 (16)
O1	0.0289 (15)	0.077 (2)	0.073 (2)	0.0088 (14)	0.0005 (13)	−0.0092 (17)
O2	0.0539 (18)	0.070 (2)	0.0632 (19)	−0.0227 (15)	0.0210 (15)	0.0020 (16)
S1	0.0261 (5)	0.0609 (8)	0.0494 (7)	−0.0073 (5)	0.0045 (5)	−0.0087 (6)

Geometric parameters (Å, º) top

C1—C2	1.367 (5)	C8—C9	1.389 (4)
C1—C6	1.390 (4)	C8—N1	1.417 (4)
C1—S1	1.760 (4)	C9—C10	1.374 (5)
C2—C3	1.382 (5)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.370 (5)
C3—C4	1.371 (5)	C10—Cl1	1.746 (3)
C3—H3	0.9300	C11—C12	1.376 (4)
C4—C5	1.384 (5)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.375 (5)
C5—C6	1.376 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.477 (5)	N1—H1	0.8600
C7—N2	1.310 (4)	N2—S1	1.635 (3)
C7—N1	1.343 (4)	O1—S1	1.432 (3)
C8—C13	1.384 (4)	O2—S1	1.428 (3)

C2—C1—C6	122.5 (3)	C10—C9—H9	120.4
C2—C1—S1	130.4 (3)	C8—C9—H9	120.4
C6—C1—S1	107.1 (3)	C11—C10—C9	122.3 (3)
C1—C2—C3	117.7 (4)	C11—C10—Cl1	119.2 (3)
C1—C2—H2	121.2	C9—C10—Cl1	118.5 (3)
C3—C2—H2	121.2	C10—C11—C12	118.0 (3)
C4—C3—C2	120.7 (4)	C10—C11—H11	121.0
C4—C3—H3	119.6	C12—C11—H11	121.0
C2—C3—H3	119.6	C13—C12—C11	121.3 (3)
C3—C4—C5	121.3 (4)	C13—C12—H12	119.3
C3—C4—H4	119.4	C11—C12—H12	119.3
C5—C4—H4	119.4	C12—C13—C8	120.0 (3)
C6—C5—C4	118.7 (4)	C12—C13—H13	120.0
C6—C5—H5	120.7	C8—C13—H13	120.0
C4—C5—H5	120.7	C7—N1—C8	130.1 (3)
C5—C6—C1	119.2 (3)	C7—N1—H1	115.0
C5—C6—C7	131.3 (3)	C8—N1—H1	115.0
C1—C6—C7	109.5 (3)	C7—N2—S1	109.9 (2)
N2—C7—N1	122.9 (3)	O2—S1—O1	115.88 (17)
N2—C7—C6	116.9 (3)	O2—S1—N2	110.41 (16)
N1—C7—C6	120.2 (3)	O1—S1—N2	109.76 (16)
C13—C8—C9	119.3 (3)	O2—S1—C1	111.86 (17)
C13—C8—N1	123.8 (3)	O1—S1—C1	110.64 (17)
C9—C8—N1	116.9 (3)	N2—S1—C1	96.63 (15)
C10—C9—C8	119.1 (3)

C6—C1—C2—C3	−0.3 (6)	Cl1—C10—C11—C12	179.7 (3)
S1—C1—C2—C3	−179.8 (3)	C10—C11—C12—C13	−0.3 (6)
C1—C2—C3—C4	0.3 (6)	C11—C12—C13—C8	0.6 (6)
C2—C3—C4—C5	−0.1 (6)	C9—C8—C13—C12	−0.5 (5)
C3—C4—C5—C6	0.0 (6)	N1—C8—C13—C12	178.3 (3)
C4—C5—C6—C1	−0.1 (5)	N2—C7—N1—C8	4.0 (6)
C4—C5—C6—C7	178.8 (4)	C6—C7—N1—C8	−174.8 (3)
C2—C1—C6—C5	0.2 (6)	C13—C8—N1—C7	−3.2 (6)
S1—C1—C6—C5	179.8 (3)	C9—C8—N1—C7	175.6 (3)
C2—C1—C6—C7	−178.9 (3)	N1—C7—N2—S1	−179.4 (3)
S1—C1—C6—C7	0.8 (4)	C6—C7—N2—S1	−0.6 (4)
C5—C6—C7—N2	−179.1 (4)	C7—N2—S1—O2	−115.4 (3)
C1—C6—C7—N2	−0.1 (4)	C7—N2—S1—O1	115.7 (3)
C5—C6—C7—N1	−0.2 (6)	C7—N2—S1—C1	0.9 (3)
C1—C6—C7—N1	178.7 (3)	C2—C1—S1—O2	−66.3 (4)
C13—C8—C9—C10	0.1 (5)	C6—C1—S1—O2	114.1 (3)
N1—C8—C9—C10	−178.8 (3)	C2—C1—S1—O1	64.5 (4)
C8—C9—C10—C11	0.2 (6)	C6—C1—S1—O1	−115.0 (3)
C8—C9—C10—Cl1	−179.6 (3)	C2—C1—S1—N2	178.6 (4)
C9—C10—C11—C12	−0.1 (6)	C6—C1—S1—N2	−1.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2	0.93	2.28	2.901 (5)	124
N1—H1···O1ⁱ	0.86	2.24	3.084 (4)	165
C5—H5···O1ⁱ	0.93	2.51	3.396 (4)	159
C2—H2···O2ⁱⁱ	0.93	2.42	3.302 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₁₃H₉ClN₂O₂S
M_r	292.73
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.2223 (10), 7.9138 (12), 11.2175 (17)
α, β, γ (°)	96.178 (6), 98.840 (5), 97.574 (5)
V (Å³)	622.63 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.28 × 0.10 × 0.08

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.947, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	10481, 2700, 1244
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.115, 0.98
No. of reflections	2700
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.26

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···N2	0.93	2.28	2.901 (5)	124
N1—H1···O1ⁱ	0.86	2.24	3.084 (4)	165
C5—H5···O1ⁱ	0.93	2.51	3.396 (4)	159
C2—H2···O2ⁱⁱ	0.93	2.42	3.302 (4)	158

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha. The authors also acknowledge technical support provided by Bana International, Karachi, Pakistan.

References

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