N-(2-Amino-5-chloro­phen­yl)-2-bromo­benzene­sulfonamide

Altamura, M.; Fedi, V.; Nannicini, R.; Paoli, P.; Rossi, P.

doi:10.1107/S160053681204562X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3308-o3309

doi:10.1107/S160053681204562X

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N-(2-Amino-5-chlorophenyl)-2-bromobenzenesulfonamide

Maria Altamura,^a Valentina Fedi,^a Rossano Nannicini,^a Paola Paoli ^b ^* and Patrizia Rossi ^b

^aChemistry Department, Menarini Ricerche S.p.A., Via dei Sette Santi 3, I-50131 Firenze, Italy, and ^bDipartimento Energetica "Sergio Stecco", University of Firenze, Via S. Marta 3, I-50139 Firenze, Italy
^*Correspondence e-mail: paolapaoli@unifi.it

(Received 22 October 2012; accepted 5 November 2012; online 10 November 2012)

In the title compound, C₁₂H₁₀BrClN₂O₂S, the sulfonamide group adopts a staggered conformation about the N—S bond [the C—S—N—H torsion angle is 97 (3)°] with the N-atom lone pair bisecting the O=S=O angle. For the C(Ar)—S bond, the ortho-substituted C atom bisects one of O=S–N angles [the C—C—S—N torsion angle is −57.7 (3)°]. The mean planes of the aromatic rings form a dihedral angle of 75.1 (1)°. In the crystal, molecules form inversion dimers through pairs of N—H⋯NH₂ hydrogen bonds. The molecules are further consolidated into layers along the bc plane by weaker N—H⋯O interactions.

Related literature

For the synthesis of the title compound, see: Altamura et al. (2009 ). For the biological activity of sulfa drugs, see: Chegwidden et al. (2000 ); Lu & Tucker (2007 ); Tappe et al. (2008 ); Purushottamachar et al. (2008 ). For structural studies of molecules having the sulfonamide –SO₂—NH group, see: Parkin et al. (2008 ); Perlovich et al. (2009 , 2011 ); Vega-Hissi et al. (2011 ); Altamura et al. (2009, 2012 ).

Experimental

Crystal data

C₁₂H₁₀BrClN₂O₂S
M_r = 361.64
Monoclinic, P 2₁ /c
a = 13.657 (1) Å
b = 14.361 (2) Å
c = 7.0829 (9) Å
β = 100.75 (1)°
V = 1364.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 3.36 mm⁻¹
T = 298 K
0.32 × 0.26 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur3 CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.365, T_max = 0.447
6647 measured reflections
2533 independent reflections
1629 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.082
S = 0.94
2533 reflections
181 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Selected torsion angles (°)

HN1—N1—S1—C1	97 (3)
HN1—N1—S1—O1	−19 (3)
C7—N1—S1—O2	50.2 (3)
C6—C1—S1—N1	−57.7 (3)
C6—C1—S1—O1	57.8 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯N2ⁱ	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A⋯O1ⁱⁱ	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: PARST (Nardelli, 1995 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204562X/ld2080sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204562X/ld2080Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204562X/ld2080Isup3.cml

checkCIF report

Comment top

The study of the structural and conformational properties of the sulfonamide group (R—SO₂—NR₂) is essential to the comprehension of the "sulfa drugs" action. They found applications as HIV inhibitors (Lu & Tucker, 2007), antimicrobial drugs (Tappe et al., 2008), carbonic anhydrase inhibitors (Chegwidden et al., 2000), anti-tumor agents (Purushottamachar et al., 2008), just to name a few. In this respect a lot of publications have appeared reporting structural data of compounds containing the sulfonamide function (Parkin et al., 2008, Altamura et al., 2009, Perlovich et al., 2009, Perlovich et al., 2011,Vega-Hissi et al., 2011, Altamura et al., 2012). The molecule, as expected, has a staggered conformation about the N—S bond, with the N lone pair bisecting the OŜO angle (Table 1, Fig. 1). The value of the dihedral angle C6—C1—S1—O1 (Table 1) is also in the range observed for arylsulfonamides bearing a non-hydrogen atom in ortho position (a bromine atom in this case). The sulfonamide nitrogen atom is almost planar- trigonal (Σ<N=357 (3)°). The aromatic rings are almost perpendicular to each other with a dihedral angle of 75.1 (1)°. In the crystal, dimers are formed by a couple of complementary hydrogen bonds involving the nitrogen atom of the sulfonamide grouping as a donor and amino nitrogen as an acceptor (Table 2). Dimers form layers along bc plane through weaker NH₂···SO₂ H-bonds between the amino group and an oxygen atom of the sulfonamide moiety (Table 2). The remaining amine H atom (HN2B) appears to be involved in bifurcated intra-molecular contacts with the oxygen and the nitrogen atoms of the sulfonamide group (HN2B···O2 = 2.72 (3) Å, N2—HN2B···O2 = 132 (3)°; HN2B···N1 = 2.58 (4) Å, N2—HN2B···N1 = 98 (3)°), which could contribute in stabilization of the observed molecular conformation.

Related literature top

For the synthesis of the title compound, see: Altamura et al. (2009). For the biological activity of sulfa drugs, see: Chegwidden et al. (2000); Lu & Tucker (2007); Tappe et al. (2008); Purushottamachar et al. (2008). For structural studies of molecules having the sulfonamide –SO₂—NH group, see: Parkin et al. (2008); Perlovich et al. (2009, 2011); Vega-Hissi et al. (2011); Altamura et al. (2009, 2012).

Experimental top

For the synthesis of the title compound, see: Altamura et al. (2009). Crystals of the title compound suitable for single-crystal X-ray diffraction analysis were obtained by slow evaporation of an ethyl acetate/hexane solution of N-(2-amino-5-chlorophenyl)-2-bromobenzenesulfonamide.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis CCD (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995).

Figures top

	Fig. 1. The structure of the title compound showing labelling and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal structure of the title compound as viewed along the a axis. Hydrogen bonds are shown as dashed lines.

N-(2-Amino-5-chlorophenyl)-2-bromobenzenesulfonamide top

Crystal data top

C₁₂H₁₀BrClN₂O₂S	Z = 4
M_r = 361.64	F(000) = 720
Monoclinic, P2₁/c	D_x = 1.760 Mg m⁻³
a = 13.657 (1) Å	Mo Kα radiation, λ = 0.71069 Å
b = 14.361 (2) Å	µ = 3.36 mm⁻¹
c = 7.0829 (9) Å	T = 298 K
β = 100.75 (1)°	Prismatic, colourless
V = 1364.8 (3) Å³	0.32 × 0.26 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur3 CCD diffractometer	2533 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 16.4547 pixels mm^-1	θ_max = 27.3°, θ_min = 4.5°
ω scans	h = −16→16
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −17→18
T_min = 0.365, T_max = 0.447	l = −8→8
6647 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0371P)²] where P = (F_o² + 2F_c²)/3
2533 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₂H₁₀BrClN₂O₂S	V = 1364.8 (3) Å³
M_r = 361.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.657 (1) Å	µ = 3.36 mm⁻¹
b = 14.361 (2) Å	T = 298 K
c = 7.0829 (9) Å	0.32 × 0.26 × 0.22 mm
β = 100.75 (1)°

Data collection top

Oxford Diffraction Xcalibur3 CCD diffractometer	2533 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1629 reflections with I > 2σ(I)
T_min = 0.365, T_max = 0.447	R_int = 0.028
6647 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.32 e Å⁻³
2533 reflections	Δρ_min = −0.38 e Å⁻³
181 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.09409 (17)	0.35073 (16)	0.8889 (4)	0.0597 (7)
O2	0.11627 (17)	0.51070 (16)	1.0184 (3)	0.0530 (6)
S1	0.13873 (6)	0.44073 (6)	0.88946 (13)	0.0402 (2)
Cl1	0.37936 (7)	0.67877 (7)	0.45078 (14)	0.0597 (3)
Br1	0.26467 (3)	0.30924 (3)	0.61701 (6)	0.0772 (2)
C1	0.2700 (2)	0.4257 (2)	0.9480 (5)	0.0353 (8)
C2	0.3192 (3)	0.4646 (2)	1.1197 (5)	0.0501 (9)
H2	0.2842	0.5022	1.1912	0.060*
C3	0.4190 (3)	0.4482 (3)	1.1847 (6)	0.0648 (11)
H3	0.4509	0.4743	1.3000	0.078*
C4	0.4715 (3)	0.3937 (3)	1.0807 (6)	0.0626 (11)
H4	0.5389	0.3829	1.1258	0.075*
C5	0.4252 (3)	0.3548 (2)	0.9097 (6)	0.0527 (10)
H5	0.4611	0.3183	0.8380	0.063*
C6	0.3248 (2)	0.3706 (2)	0.8458 (5)	0.0419 (8)
C7	0.1417 (2)	0.5706 (2)	0.6229 (4)	0.0313 (7)
C8	0.2332 (2)	0.5803 (2)	0.5710 (4)	0.0362 (8)
H8	0.2742	0.5286	0.5697	0.043*
C9	0.2643 (2)	0.6666 (2)	0.5209 (5)	0.0373 (8)
C10	0.2038 (3)	0.7433 (2)	0.5235 (4)	0.0398 (8)
H10	0.2252	0.8016	0.4911	0.048*
C11	0.1118 (2)	0.7335 (2)	0.5742 (4)	0.0391 (8)
H11	0.0712	0.7854	0.5745	0.047*
C12	0.0789 (2)	0.6470 (2)	0.6248 (4)	0.0292 (7)
N1	0.1089 (2)	0.48048 (18)	0.6746 (4)	0.0380 (7)
HN1	0.091 (2)	0.443 (2)	0.595 (5)	0.046*
N2	−0.0166 (2)	0.6362 (2)	0.6676 (4)	0.0428 (8)
HN2A	−0.045 (3)	0.689 (2)	0.687 (5)	0.051*
HN2B	−0.021 (3)	0.597 (2)	0.750 (5)	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0480 (14)	0.0428 (15)	0.088 (2)	−0.0138 (13)	0.0117 (13)	0.0216 (13)
O2	0.0536 (15)	0.0621 (16)	0.0470 (15)	0.0154 (13)	0.0193 (12)	−0.0013 (12)
S1	0.0373 (5)	0.0376 (5)	0.0473 (5)	−0.0003 (4)	0.0122 (4)	0.0064 (4)
Cl1	0.0463 (6)	0.0695 (7)	0.0655 (7)	−0.0078 (5)	0.0160 (5)	0.0115 (5)
Br1	0.0876 (4)	0.0665 (3)	0.0700 (3)	0.0282 (2)	−0.0049 (2)	−0.0302 (2)
C1	0.0377 (19)	0.0259 (18)	0.043 (2)	−0.0002 (15)	0.0094 (16)	0.0059 (14)
C2	0.053 (2)	0.052 (2)	0.044 (2)	0.008 (2)	0.0050 (18)	−0.0004 (17)
C3	0.062 (3)	0.071 (3)	0.054 (3)	0.001 (2)	−0.009 (2)	−0.006 (2)
C4	0.042 (2)	0.065 (3)	0.077 (3)	0.006 (2)	0.003 (2)	0.012 (2)
C5	0.048 (2)	0.051 (2)	0.062 (3)	0.009 (2)	0.016 (2)	0.0096 (19)
C6	0.044 (2)	0.033 (2)	0.049 (2)	0.0027 (17)	0.0091 (17)	0.0018 (15)
C7	0.0335 (19)	0.0278 (18)	0.0318 (18)	−0.0037 (16)	0.0040 (14)	0.0002 (13)
C8	0.040 (2)	0.0309 (19)	0.038 (2)	0.0035 (16)	0.0072 (15)	0.0028 (14)
C9	0.0369 (19)	0.043 (2)	0.0308 (19)	−0.0014 (17)	0.0046 (14)	0.0013 (14)
C10	0.052 (2)	0.032 (2)	0.034 (2)	−0.0057 (18)	0.0023 (17)	0.0065 (14)
C11	0.048 (2)	0.034 (2)	0.0329 (19)	0.0083 (18)	0.0013 (16)	−0.0009 (14)
C12	0.0305 (18)	0.0313 (18)	0.0250 (17)	0.0009 (16)	0.0029 (13)	−0.0030 (13)
N1	0.0424 (17)	0.0304 (16)	0.0391 (17)	−0.0034 (14)	0.0021 (13)	−0.0018 (12)
N2	0.0429 (19)	0.040 (2)	0.046 (2)	0.0065 (16)	0.0081 (15)	−0.0001 (14)

Geometric parameters (Å, º) top

O1—S1	1.429 (2)	C5—H5	0.9300
O2—S1	1.429 (2)	C7—C8	1.375 (4)
S1—N1	1.605 (3)	C7—C12	1.395 (4)
S1—C1	1.776 (3)	C7—N1	1.438 (4)
Cl1—C9	1.743 (3)	C8—C9	1.377 (4)
Br1—C6	1.892 (3)	C8—H8	0.9300
C1—C6	1.383 (4)	C9—C10	1.379 (4)
C1—C2	1.392 (4)	C10—C11	1.376 (4)
C2—C3	1.375 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.390 (4)
C3—C4	1.366 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—N2	1.402 (4)
C4—C5	1.377 (5)	N1—HN1	0.78 (3)
C4—H4	0.9300	N2—HN2A	0.87 (3)
C5—C6	1.380 (4)	N2—HN2B	0.82 (3)

O1—S1—O2	119.70 (16)	C8—C7—C12	121.0 (3)
O1—S1—N1	106.66 (16)	C8—C7—N1	120.0 (3)
O2—S1—N1	108.00 (14)	C12—C7—N1	119.0 (3)
O1—S1—C1	107.58 (14)	C7—C8—C9	119.9 (3)
O2—S1—C1	105.30 (15)	C7—C8—H8	120.0
N1—S1—C1	109.34 (15)	C9—C8—H8	120.0
C6—C1—C2	117.8 (3)	C8—C9—C10	120.1 (3)
C6—C1—S1	124.6 (3)	C8—C9—Cl1	120.1 (3)
C2—C1—S1	117.2 (3)	C10—C9—Cl1	119.8 (3)
C3—C2—C1	120.7 (3)	C11—C10—C9	120.0 (3)
C3—C2—H2	119.7	C11—C10—H10	120.0
C1—C2—H2	119.7	C9—C10—H10	120.0
C4—C3—C2	120.4 (4)	C10—C11—C12	120.9 (3)
C4—C3—H3	119.8	C10—C11—H11	119.6
C2—C3—H3	119.8	C12—C11—H11	119.6
C3—C4—C5	120.4 (4)	C11—C12—C7	118.1 (3)
C3—C4—H4	119.8	C11—C12—N2	120.9 (3)
C5—C4—H4	119.8	C7—C12—N2	120.9 (3)
C4—C5—C6	119.1 (3)	C7—N1—S1	121.7 (2)
C4—C5—H5	120.4	C7—N1—HN1	120 (3)
C6—C5—H5	120.4	S1—N1—HN1	115 (3)
C5—C6—C1	121.6 (3)	C12—N2—HN2A	114 (2)
C5—C6—Br1	116.7 (3)	C12—N2—HN2B	116 (3)
C1—C6—Br1	121.6 (2)	HN2A—N2—HN2B	112 (3)

HN1—N1—S1—C1	97 (3)	C6—C1—S1—N1	−57.7 (3)
HN1—N1—S1—O1	−19 (3)	C6—C1—S1—O1	57.8 (3)
C7—N1—S1—O2	50.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N2ⁱ	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A···O1ⁱⁱ	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₀BrClN₂O₂S
M_r	361.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.657 (1), 14.361 (2), 7.0829 (9)
β (°)	100.75 (1)
V (Å³)	1364.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.36
Crystal size (mm)	0.32 × 0.26 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur3 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.365, 0.447
No. of measured, independent and observed [I > 2σ(I)] reflections	6647, 2533, 1629
R_int	0.028

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.082, 0.94
No. of reflections	2533
No. of parameters	181
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.38

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PARST (Nardelli, 1995).

Selected torsion angles (º) top

HN1—N1—S1—C1	97 (3)	C6—C1—S1—N1	−57.7 (3)
HN1—N1—S1—O1	−19 (3)	C6—C1—S1—O1	57.8 (3)
C7—N1—S1—O2	50.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···N2ⁱ	0.78 (3)	2.26 (3)	3.022 (4)	166 (3)
N2—HN2A···O1ⁱⁱ	0.87 (3)	2.45 (3)	3.258 (4)	154 (3)

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

Acknowledgements

The authors acknowledge the CRIST (Centro di Cristallografia Strutturale, University of Firenze), where the data collection was performed.

References

Altamura, M., Fedi, V., Giannotti, D., Paoli, P. & Rossi, P. (2009). New J. Chem. 33, 2219–2231. Web of Science CSD CrossRef CAS Google Scholar
Altamura, M., Fedi, V., Nannicini, R., Paoli, P. & Rossi, P. (2012). Acta Cryst. E68, o3144–o3145. CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Chegwidden, W. R., Carter, N. D. & Edwards, Y. H. (2000). In The Carbonic Anhydrases New Horizons. Basel: Birkhauser Verlag. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Lu, R. J. & Tucker, J. A. (2007). J. Med. Chem. 50, 6535–6544. Web of Science CrossRef PubMed CAS Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Parkin, A., Collins, A., Gilmore, C. J. & Wilson, C. C. (2008). Acta Cryst. B64, 66–71. Web of Science CrossRef IUCr Journals Google Scholar
Perlovich, G. L., Ryzhakov, A. M., Tkachev, T. T. & Hansen, L. K. (2011). Cryst. Growth Des. 11, 1067–1081. Web of Science CSD CrossRef CAS Google Scholar
Perlovich, G. L., Tkachev, V. V., Strakhova, N. N., Kazachenko, V. P., Volkova, T. V., Surov, O. V., Schaper, K.-J. & Raevsky, O. A. (2009). J. Pharm. Sci. 98, 4738–4755. Web of Science CSD CrossRef PubMed CAS Google Scholar
Purushottamachar, P., Khandelwal, A., Vasaitis, T. S., Bruno, R. D., Gediya, L. K. & Njar, V. C. O. (2008). Bioorg. Med. Chem. 16, 3519–3529. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tappe, W., Zarfl, C., Kummer, S., Burauel, P., Vereecken, H. & Groeneweg, J. (2008). Chemosphere, 72, 836–843. Web of Science CrossRef PubMed CAS Google Scholar
Vega-Hissi, E. G., Andrada, M. F., Zamarbide, G. N., Estrada, M. R. & Tomas-Vert, F. (2011). J. Mol. Model. 17, 1317–1323. Web of Science CAS PubMed Google Scholar