Crystal structure of 4-bromo-N-(2-hydroxy­phen­yl)benzamide

Moreno-Fuquen, R.; Melo, V.; Ellena, J.

doi:10.1107/S1600536814024696

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1261-o1262

doi:10.1107/S1600536814024696

Open

access

Crystal structure of 4-bromo-N-(2-hydroxyphenyl)benzamide

Rodolfo Moreno-Fuquen,^a ^* Vanessa Melo ^a and Javier Ellena ^b

^aDepartamento de Química – Facultad de Ciencias Naturales y Exactas, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia, and ^bInstituto de Física de São Carlos, IFSC, Universidade de São Paulo, USP, São Carlos, SP, Brazil
^*Correspondence e-mail: rodimo26@yahoo.es

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 10 November 2014; accepted 10 November 2014; online 15 November 2014)

In the title compound, C₁₃H₁₀BrNO₂, the mean plane of the non-H atoms of the central amide C—N—C(=O)—C fragment (r.m.s. deviation = 0.004 Å) forms a dihedral angle of 73.97 (12)° with the hydroxy-substituted benzene ring and 25.42 (19)° with the bromo-substituted benzene ring. The two aromatic rings are inclined to one another by 80.7 (2)°. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming chains along [010]. The chains are linked by weak C—H⋯O hydrogen bonds, forming sheets parallel to (100), and enclosing R³₃(17) and R³₂(9) ring motifs.

Keywords: crystal structure; benzamide; hydroxyaniline; hydrogen bonding.

CCDC reference: 1033535

1. Related literature

For the antiprotozoal and antimicrobial properties of phenylbenzamides, see: Ríos Martínez et al. (2014 ); Şener et al. (2000 ). For active metabolites of benzoxazoles, see: Mobinikhaledi et al. (2006 ). For studies of phenylbenzamides as inhibitors of tyrosine kinases, see: Capdeville et al. (2002 ). For studies of phenylbenzamides as inducers of apoptosis in biological processes, see: Olsson et al. (2002 ). For related structures, see: Fun et al. (2012 ); Hibbert et al. (1998 ).

2. Experimental

2.1. Crystal data

C₁₃H₁₀BrNO₂
M_r = 292.13
Monoclinic, P 2₁ /c
a = 23.4258 (10) Å
b = 5.6473 (1) Å
c = 9.2464 (3) Å
β = 93.008 (1)°
V = 1221.54 (7) Å³
Z = 4
Mo Kα radiation
μ = 3.35 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.13 mm

2.2. Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.537, T_max = 0.662
21458 measured reflections
2490 independent reflections
1664 reflections with I > 2σ(I)
R_int = 0.063

2.3. Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.168
S = 0.99
2490 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—HO2⋯O1ⁱ	0.82	2.00	2.682 (3)	141
N1—H1⋯O1ⁱⁱ	0.86	2.02	2.824 (3)	155
C6—H6⋯O2ⁱⁱⁱ	0.93	2.56	3.458 (5)	164
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; 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, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 1033535

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814024696/su5019sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024696/su5019Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814024696/su5019Isup3.cml

checkCIF report

Comment top

The crystal structure determination of the title compound (I), is part of a study on phenylbenzamides carried out in our research group, and they are synthesized from the reaction of picryl benzoates with 2-hydroxy-aniline. These compounds have received extensive attention because of their antiprotozoal (Ríos Martínez et al., 2014) and anti-microbialactivity (Şener et al., 2000), and as active metabolites of benzoxazoles (Mobinikhaledi et al., 2006). They have also been studied as inhibitors of tyrosine kinases (Capdeville et al., 2002) and inducers of apoptosis in the tumor development process (Olsson et al., 2002). Similar compounds to (I) have been reported in the literature, viz. 4-bromo-N-phenylbenzamide (II) (Fun et al., 2012) and 2-hydroxy-N-benzoylaniline (III) (Hibbert et al., 1998).

The molecular structure of (I) is shown in Fig. 1. The central amide moiety, C8—N1-C7(═O1)—C1, is essentially planar (r.m.s. deviation for all non-H atoms = 0.0026 Å) and it forms dihedral angles of 73.97 (12)° with the hydroxy-substituted phenyl ring and 25.42 (19)° with the bromo-substituted benzene ring. The bond lengths and angles within the molecule of (I) are in a good agreement with those found in the related compounds (II) and (III), although the N1-C7 bond length in the central amide segment, is slightly increased in structure (II), [C1-C7= 1.361 (2)Å].

In the crystal of (I), molecules are linked by O-H···O and N-H···O hydrogen bonds of medium-strength and weak C-H···O intermolecular contacts forming sheets parallel to (100) (Table 1 and Fig. 2). The O2-HO2···O1 hydrogen bonds are responsible for crystal growth in the b direction. In this interaction, the hydroxy O2-HO2 group in the molecule at (x, y, z) acts as a hydrogen-bond donor to atom O1 of the carbonyl group at (x ,-y-3/2, z-1/2). In turn, the N1-H1···O1 hydrogen bonds and weak C6-H6···O2 interactions, complement crystal growth in the c direction (see Fig. 2). The N1-H1 group of the amide moiety in the molecule at (x ,y, z) acts as hydrogen bond donor to carbonyl atom O1 in the molecule at (x, -y-1/2, z-1/2) and the C6-H6 group in the molecule at (x, y, z) acts as a hydrogen bond donor to atom O2 in the molecule at (x, y+1 ,z). Very likely, these interactions are responsible for the twist of the rings with respect to the central amide moiety. The combination of these interactions generate edge-fused R³₃(17) and R³₂(9) ring motifs.

Related literature top

For the antiprotozoal and antimicrobial properties of phenylbenzamides, see: Ríos Martínez et al. (2014); Şener et al. (2000). For active metabolites of benzoxazoles, see: Mobinikhaledi et al. (2006). For studies of phenylbenzamides as inhibitors of tyrosine kinases, see: Capdeville et al. (2002). For studies of phenylbenzamides as inducers of apoptosis in biological processes, see: Olsson et al. (2002). For related structures, see: Fun et al. (2012); Hibbert et al. (1998).

Experimental top

4-bromobenzoate 2,4,6-trinitrophenyl (0.050 g, 0.117 mmol) and 2-hydroxyaniline (0.0254 g) in molar ratio 1:2, were dissolved in 15 mL of toluene and mixed for 6 h under reflux and constant stirring. On completion of the reaction part of the solvent was evaporated and a crystalline black solid was obtained. [m.p.: 454 (1) K].

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

The molecular structure of the title compound (I), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Part of the crystal packing of the title compound (I) viewed along the a axis, showing the formation of R³₃(17) and R³₂(9) ring motifs within the two-dimensional hydrogen bonded network running parallel to (100). Hydrogen bonds are shown as dashed lines; see Table 1 for details [symmetry codes: (i) x, -y-3/2, z-1/2; (ii) x, -y-1/2, z-1/2; (iii) x, y+1, z].

4-Bromo-N-(2-hydroxyphenyl)benzamide top

Crystal data top

C₁₃H₁₀BrNO₂	F(000) = 584
M_r = 292.13	D_x = 1.588 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 454(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 23.4258 (10) Å	Cell parameters from 2490 reflections
b = 5.6473 (1) Å	θ = 3.5–26.4°
c = 9.2464 (3) Å	µ = 3.35 mm⁻¹
β = 93.008 (1)°	T = 295 K
V = 1221.54 (7) Å³	Block, black
Z = 4	0.20 × 0.18 × 0.13 mm

Data collection top

Nonius KappaCCD diffractometer	2490 independent reflections
Radiation source: fine-focus sealed tube	1664 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
CCD rotation images, thick slices scans	θ_max = 26.4°, θ_min = 3.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→29
T_min = 0.537, T_max = 0.662	k = −7→6
21458 measured reflections	l = −11→11

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0999P)² + 0.5651P] where P = (F_o² + 2F_c²)/3
2490 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₁₃H₁₀BrNO₂	V = 1221.54 (7) Å³
M_r = 292.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.4258 (10) Å	µ = 3.35 mm⁻¹
b = 5.6473 (1) Å	T = 295 K
c = 9.2464 (3) Å	0.20 × 0.18 × 0.13 mm
β = 93.008 (1)°

Data collection top

Nonius KappaCCD diffractometer	2490 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1664 reflections with I > 2σ(I)
T_min = 0.537, T_max = 0.662	R_int = 0.063
21458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 0.99	Δρ_max = 0.61 e Å⁻³
2490 reflections	Δρ_min = −0.68 e Å⁻³
154 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
Br1	0.46192 (2)	1.31657 (9)	0.85256 (8)	0.1081 (3)
O1	0.23094 (11)	0.5820 (4)	0.8853 (2)	0.0546 (6)
C7	0.24418 (16)	0.7116 (6)	0.7843 (3)	0.0462 (8)
C9	0.15972 (16)	0.4064 (6)	0.5411 (4)	0.0513 (8)
O2	0.20914 (13)	0.3579 (5)	0.4767 (3)	0.0700 (8)
HO2	0.2040	0.2472	0.4201	0.105*
N1	0.21228 (13)	0.7256 (5)	0.6607 (3)	0.0520 (7)
H1	0.2235	0.8168	0.5933	0.062*
C1	0.29740 (16)	0.8587 (6)	0.7961 (3)	0.0490 (8)
C6	0.30259 (17)	1.0664 (6)	0.7177 (4)	0.0565 (9)
H6	0.2728	1.1161	0.6543	0.068*
C8	0.16058 (15)	0.5964 (6)	0.6357 (3)	0.0500 (8)
C5	0.3522 (2)	1.1998 (7)	0.7340 (5)	0.0675 (11)
H5	0.3560	1.3385	0.6811	0.081*
C2	0.34181 (18)	0.7886 (7)	0.8900 (4)	0.0604 (9)
H2	0.3384	0.6499	0.9431	0.073*
C4	0.39549 (18)	1.1262 (7)	0.8281 (5)	0.0665 (10)
C13	0.1110 (2)	0.6596 (7)	0.7011 (4)	0.0683 (11)
H13	0.1113	0.7876	0.7645	0.082*
C10	0.11003 (19)	0.2786 (8)	0.5152 (5)	0.0696 (11)
H10	0.1096	0.1490	0.4532	0.083*
C11	0.0610 (2)	0.3429 (9)	0.5812 (5)	0.0816 (13)
H11	0.0275	0.2566	0.5635	0.098*
C3	0.39140 (18)	0.9208 (7)	0.9065 (5)	0.0704 (11)
H3	0.4214	0.8717	0.9694	0.084*
C12	0.06136 (19)	0.5340 (10)	0.6729 (5)	0.0851 (14)
H12	0.0280	0.5786	0.7160	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0702 (4)	0.0749 (4)	0.1796 (7)	−0.0166 (2)	0.0112 (4)	−0.0221 (3)
O1	0.0774 (17)	0.0477 (13)	0.0385 (12)	−0.0068 (12)	0.0028 (11)	0.0028 (10)
C7	0.062 (2)	0.0424 (17)	0.0345 (16)	0.0026 (15)	0.0049 (15)	−0.0055 (13)
C9	0.059 (2)	0.0450 (18)	0.0493 (18)	0.0008 (16)	−0.0007 (16)	0.0039 (15)
O2	0.0772 (19)	0.0527 (14)	0.0812 (18)	0.0004 (13)	0.0136 (15)	−0.0171 (13)
N1	0.071 (2)	0.0511 (15)	0.0340 (14)	−0.0087 (14)	0.0044 (13)	0.0005 (12)
C1	0.064 (2)	0.0451 (17)	0.0381 (16)	−0.0018 (15)	0.0080 (15)	−0.0056 (14)
C6	0.072 (2)	0.0474 (19)	0.0498 (19)	−0.0078 (17)	−0.0011 (17)	−0.0017 (15)
C8	0.061 (2)	0.0484 (18)	0.0405 (16)	0.0038 (16)	−0.0009 (15)	0.0046 (14)
C5	0.088 (3)	0.048 (2)	0.068 (2)	−0.0111 (19)	0.019 (2)	−0.0034 (17)
C2	0.069 (2)	0.052 (2)	0.060 (2)	0.0022 (18)	−0.0012 (19)	−0.0004 (16)
C4	0.062 (2)	0.056 (2)	0.082 (3)	−0.0074 (19)	0.012 (2)	−0.014 (2)
C13	0.075 (3)	0.075 (3)	0.056 (2)	0.010 (2)	0.0069 (19)	−0.0066 (18)
C10	0.072 (3)	0.065 (2)	0.070 (2)	−0.011 (2)	−0.007 (2)	−0.005 (2)
C11	0.062 (3)	0.099 (4)	0.081 (3)	−0.015 (2)	−0.013 (2)	0.007 (3)
C3	0.062 (2)	0.062 (2)	0.086 (3)	0.001 (2)	−0.004 (2)	−0.013 (2)
C12	0.056 (3)	0.119 (4)	0.081 (3)	0.010 (3)	0.005 (2)	0.005 (3)

Geometric parameters (Å, º) top

Br1—C4	1.895 (4)	C8—C13	1.384 (5)
O1—C7	1.239 (4)	C5—C4	1.365 (7)
C7—N1	1.334 (4)	C5—H5	0.9300
C7—C1	1.497 (5)	C2—C3	1.383 (6)
C9—O2	1.357 (4)	C2—H2	0.9300
C9—C10	1.380 (5)	C4—C3	1.374 (6)
C9—C8	1.384 (5)	C13—C12	1.375 (7)
O2—HO2	0.8200	C13—H13	0.9300
N1—C8	1.423 (5)	C10—C11	1.378 (7)
N1—H1	0.8600	C10—H10	0.9300
C1—C2	1.377 (5)	C11—C12	1.372 (7)
C1—C6	1.388 (5)	C11—H11	0.9300
C6—C5	1.387 (6)	C3—H3	0.9300
C6—H6	0.9300	C12—H12	0.9300

O1—C7—N1	122.0 (3)	C1—C2—C3	121.1 (4)
O1—C7—C1	120.9 (3)	C1—C2—H2	119.4
N1—C7—C1	117.2 (3)	C3—C2—H2	119.4
O2—C9—C10	123.4 (3)	C5—C4—C3	121.6 (4)
O2—C9—C8	116.7 (3)	C5—C4—Br1	118.7 (3)
C10—C9—C8	119.9 (4)	C3—C4—Br1	119.7 (3)
C9—O2—HO2	109.5	C12—C13—C8	120.3 (4)
C7—N1—C8	122.9 (3)	C12—C13—H13	119.9
C7—N1—H1	118.6	C8—C13—H13	119.9
C8—N1—H1	118.6	C11—C10—C9	120.1 (4)
C2—C1—C6	119.2 (3)	C11—C10—H10	120.0
C2—C1—C7	119.0 (3)	C9—C10—H10	120.0
C6—C1—C7	121.7 (3)	C12—C11—C10	120.2 (4)
C5—C6—C1	119.9 (4)	C12—C11—H11	119.9
C5—C6—H6	120.1	C10—C11—H11	119.9
C1—C6—H6	120.1	C4—C3—C2	118.6 (4)
C9—C8—C13	119.4 (4)	C4—C3—H3	120.7
C9—C8—N1	119.0 (3)	C2—C3—H3	120.7
C13—C8—N1	121.5 (3)	C11—C12—C13	120.1 (4)
C4—C5—C6	119.6 (4)	C11—C12—H12	120.0
C4—C5—H5	120.2	C13—C12—H12	120.0
C6—C5—H5	120.2

O1—C7—N1—C8	0.8 (5)	C6—C1—C2—C3	−0.3 (5)
C1—C7—N1—C8	−179.6 (3)	C7—C1—C2—C3	−178.8 (3)
O1—C7—C1—C2	24.5 (5)	C6—C5—C4—C3	0.7 (6)
N1—C7—C1—C2	−155.1 (3)	C6—C5—C4—Br1	−178.2 (3)
O1—C7—C1—C6	−153.9 (3)	C9—C8—C13—C12	0.3 (6)
N1—C7—C1—C6	26.5 (4)	N1—C8—C13—C12	178.8 (4)
C2—C1—C6—C5	0.3 (5)	O2—C9—C10—C11	−178.0 (4)
C7—C1—C6—C5	178.7 (3)	C8—C9—C10—C11	1.3 (6)
O2—C9—C8—C13	177.9 (3)	C9—C10—C11—C12	−0.1 (7)
C10—C9—C8—C13	−1.4 (5)	C5—C4—C3—C2	−0.8 (6)
O2—C9—C8—N1	−0.7 (4)	Br1—C4—C3—C2	178.1 (3)
C10—C9—C8—N1	180.0 (3)	C1—C2—C3—C4	0.6 (6)
C7—N1—C8—C9	−107.5 (4)	C10—C11—C12—C13	−1.1 (7)
C7—N1—C8—C13	73.9 (5)	C8—C13—C12—C11	1.0 (7)
C1—C6—C5—C4	−0.5 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—HO2···O1ⁱ	0.82	2.00	2.682 (3)	141
N1—H1···O1ⁱⁱ	0.86	2.02	2.824 (3)	155
C6—H6···O2ⁱⁱⁱ	0.93	2.56	3.458 (5)	164

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—HO2···O1ⁱ	0.82	2.00	2.682 (3)	141
N1—H1···O1ⁱⁱ	0.86	2.02	2.824 (3)	155
C6—H6···O2ⁱⁱⁱ	0.93	2.56	3.458 (5)	164

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

Acknowledgements

RMF is grateful to the Universidad del Valle, Colombia, for partial financial support.

References

Capdeville, R., Buchdunger, E., Zimmermann, J. & Matter, A. (2002). Nat. Rev. Drug Disc. 1, 493–502. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fun, H.-K., Chantrapromma, S., Sripet, W., Ruanwas, P. & Boonnak, N. (2012). Acta Cryst. E68, o1269–o1270. CSD CrossRef IUCr Journals Google Scholar
Hibbert, F., Mills, J. F., Nyburg, S. C. & Parkins, A. W. (1998). J. Chem. Soc. Perkin Trans. 2, pp. 628–634. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mobinikhaledi, A., Forughifar, N., Shariatzadeh, S. M. & Fallah, M. (2006). Heterocycl. Commun. 12, 427-430. CrossRef CAS Google Scholar
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Olsson, A. R., Lindgren, H., Pero, R. W. & Leanderson, T. (2002). Br. J. Cancer, 86, 97-1-978. Web of Science CrossRef Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Ríos Martínez, C. H., Lagartera, L., Kaiser, M. & Dardonville, C. (2014). Eur. J. Med. Chem. 81, 481–491. PubMed Google Scholar
Şener, E. A., Bingöl, K. K., Ören, I., Arpacı, Ö. T., Yalçın, İ & Altanlar, N. (2000). Farmaco, 55, 469–476. 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