3-Bromo­meth­yl-2-chloro­meth­yl-1-phenyl­sulfon­yl-1H-indole

Chakkaravarthi, G.; Dhayalan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536808007678

organic compounds

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Volume 64| Part 4| April 2008| Page o749

doi:10.1107/S1600536808007678

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3-Bromomethyl-2-chloromethyl-1-phenylsulfonyl-1H-indole

G. Chakkaravarthi,^a ^* V. Dhayalan,^b A. K. Mohanakrishnan ^b and V. Manivannan ^c

^aDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and ^cDepartment of Physics, Presidency College, Chennai 600 005, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 19 March 2008; accepted 20 March 2008; online 29 March 2008)

In the title compound, C₁₆H₁₃BrClNO₂S, the indole mean plane forms a dihedral angle of 73.59 (19)° with the phenyl ring. The molecular structure is stabilized by weak intramolecular C—H⋯O interactions. The Br atom is disordered over two positions with site occupancy factors of 0.7 and 0.3.

Related literature

For related crystal structures, see: Chakkaravarthi et al. (2007 , 2008 ). For the biological activities of indole derivatives, see: Chai et al. (2006 ); Nieto et al. (2005 ); Olgen & Coban (2003 ).

Experimental

Crystal data

C₁₆H₁₃BrClNO₂S
M_r = 398.69
Monoclinic, P 2₁ /c
a = 11.8501 (9) Å
b = 16.3525 (13) Å
c = 8.5793 (6) Å
β = 108.766 (3)°
V = 1574.1 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.92 mm⁻¹
T = 295 (2) K
0.16 × 0.14 × 0.14 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.559, T_max = 0.665
14367 measured reflections
2770 independent reflections
1822 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.231
S = 1.06
2770 reflections
209 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.92 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2	0.93	2.51	2.877 (9)	104
C13—H13⋯O1	0.93	2.31	2.873 (10)	118
C15—H15B⋯O2	0.97	2.17	2.939 (10)	136

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808007678/bt2689sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007678/bt2689Isup2.hkl

checkCIF report

Comment top

In continuation of our studies of indole derivatives, which are known to exhibit anti-oxidant activity (Olgen & Coban, 2003), antihepatitis B virus activities (Chai et al., 2006) and antibacterial (Nieto et al., 2005) activities, we report the crystal structure of the title compound (I).

The geometric parameters of the molecule of (I) (Fig. 1) agree well with the reported structures (Chakkaravarthi et al., 2007, 2008). The indole mean plane forms a dihedral angle of 73.59 (19)° with the phenyl ring. The N1—S1—C1 plane is almost orthogonal to indole ring (dihedral angle 82.30 (22)°) and makes 76.93 (22)° with the phenyl ring. The indole mean plane and C8—C16—BR1 plane are nearly orthogonal to each other forming a dihedral angle of 82.23 (0.29)°.

The sum of bond angles around N1 (359.99°) shows that N1 is sp²-hybridized. The torsion angles O1—S1—N1—C14 and O2—S1—N1—C7 [17.8 (6)° and -33.4 (6)°, respectively] indicate the syn conformation of the sulfonyl moiety. The molecular structure is stabilized by weak intramolecular C—H···O interactions.

Related literature top

For related crystal structures, see: Chakkaravarthi et al. (2007, 2008). For the biological activities of indole derivatives, see: Chai et al. (2006); Nieto et al. (2005); Olgen & Coban (2003).

Experimental top

1-(Phenylsulfonyl)-3-(bromomethyl)-2-methylindole (0.5 g, 1.37 mmol) was dissolved in dry ccl₄(10 ml) and then powdered N-chloro succinimide was added. To this, azobisisobutyronitrle (50 mg) was also added and then refluxed for 2 h on a waterbath. After the reaction was completed, succinimide was floated on the surface of the reaction mixture. It was then filtered off and washed with CCl₄ (3 ml). The solvent was removed carefully under vacuo. The crude product was recrystallized from CCl₄. Yield:76 percentage.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic labels and 50% probability displacement ellipsoids for non-H atoms. Only major parts of the disordered atoms are drawn. Intramolecular H-bonds are shown as dashed lines.

3-Bromomethyl-2-chloromethyl-1-phenylsulfonyl-1H-indole top

Crystal data top

C₁₆H₁₃BrClNO₂S	F(000) = 800
M_r = 398.69	D_x = 1.682 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4037 reflections
a = 11.8501 (9) Å	θ = 2.5–25.0°
b = 16.3525 (13) Å	µ = 2.92 mm⁻¹
c = 8.5793 (6) Å	T = 295 K
β = 108.766 (3)°	Block, colourless
V = 1574.1 (2) Å³	0.16 × 0.14 × 0.14 mm
Z = 4

Data collection top

Bruker Kappa APEXII diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	1822 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.559, T_max = 0.665	k = −19→19
14367 measured reflections	l = −10→10

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.127P)² + 1.9456P] where P = (F_o² + 2F_c²)/3
2770 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.42 e Å⁻³
12 restraints	Δρ_min = −0.92 e Å⁻³

Crystal data top

C₁₆H₁₃BrClNO₂S	V = 1574.1 (2) Å³
M_r = 398.69	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8501 (9) Å	µ = 2.92 mm⁻¹
b = 16.3525 (13) Å	T = 295 K
c = 8.5793 (6) Å	0.16 × 0.14 × 0.14 mm
β = 108.766 (3)°

Data collection top

Bruker Kappa APEXII diffractometer	2770 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1822 reflections with I > 2σ(I)
T_min = 0.559, T_max = 0.665	R_int = 0.045
14367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	12 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.06	Δρ_max = 0.42 e Å⁻³
2770 reflections	Δρ_min = −0.92 e Å⁻³
209 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.90925 (16)	−0.10531 (12)	0.5085 (3)	0.0872 (6)
Br1	0.8135 (6)	0.1043 (5)	0.3205 (5)	0.1572 (16)	0.709 (16)
Br1A	0.7901 (4)	0.1251 (3)	0.3139 (9)	0.093 (2)	0.291 (16)
S1	0.70049 (14)	−0.13649 (11)	0.8192 (2)	0.0743 (6)
O1	0.6340 (5)	−0.1191 (4)	0.9258 (8)	0.114 (2)
O2	0.6743 (5)	−0.2077 (3)	0.7212 (8)	0.109 (2)
N1	0.6795 (4)	−0.0573 (3)	0.6922 (5)	0.0539 (11)
C1	0.8512 (6)	−0.1369 (4)	0.9320 (7)	0.0655 (17)
C2	0.8952 (7)	−0.0826 (5)	1.0604 (8)	0.097 (2)
H2	0.8449	−0.0449	1.0854	0.117*
C3	1.0161 (8)	−0.0849 (8)	1.1523 (11)	0.127 (4)
H3	1.0474	−0.0485	1.2387	0.153*
C4	1.0885 (9)	−0.1418 (7)	1.1133 (13)	0.122 (4)
H4	1.1688	−0.1441	1.1753	0.147*
C5	1.0442 (8)	−0.1951 (6)	0.9845 (13)	0.113 (3)
H5	1.0947	−0.2325	0.9590	0.135*
C6	0.9256 (7)	−0.1932 (5)	0.8934 (10)	0.086 (2)
H6	0.8953	−0.2295	0.8065	0.103*
C7	0.7000 (5)	−0.0556 (3)	0.5384 (7)	0.0574 (14)
C8	0.6681 (5)	0.0197 (3)	0.4715 (6)	0.0535 (14)
C9	0.6288 (5)	0.0680 (3)	0.5809 (5)	0.0463 (12)
C10	0.5887 (6)	0.1477 (4)	0.5707 (7)	0.0622 (15)
H10	0.5837	0.1796	0.4790	0.075*
C11	0.5563 (6)	0.1790 (4)	0.6984 (8)	0.078 (2)
H11	0.5295	0.2327	0.6939	0.094*
C12	0.5633 (7)	0.1313 (5)	0.8332 (9)	0.083 (2)
H12	0.5406	0.1537	0.9182	0.099*
C13	0.6026 (6)	0.0519 (5)	0.8471 (6)	0.0687 (18)
H13	0.6064	0.0203	0.9388	0.082*
C14	0.6365 (4)	0.0206 (3)	0.7184 (6)	0.0468 (12)
C15	0.7557 (4)	−0.1232 (4)	0.4743 (11)	0.086 (2)
H15A	0.7151	−0.1294	0.3572	0.103*
H15B	0.7464	−0.1739	0.5278	0.103*
C16	0.6722 (5)	0.0443 (4)	0.3064 (7)	0.084 (2)
H16A	0.6030	0.0777	0.2520	0.101*	0.709 (16)
H16B	0.6686	−0.0042	0.2400	0.101*	0.709 (16)
H16C	0.6052	0.0802	0.2560	0.101*	0.291 (16)
H16D	0.6645	−0.0033	0.2363	0.101*	0.291 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0663 (11)	0.0872 (13)	0.1176 (15)	0.0181 (9)	0.0429 (10)	−0.0109 (10)
Br1	0.235 (3)	0.159 (3)	0.106 (2)	−0.112 (2)	0.095 (2)	−0.0245 (15)
Br1A	0.063 (4)	0.105 (3)	0.098 (3)	−0.014 (2)	0.008 (2)	0.041 (3)
S1	0.0540 (9)	0.0688 (11)	0.0926 (12)	−0.0071 (8)	0.0129 (8)	0.0402 (9)
O1	0.082 (3)	0.142 (5)	0.130 (5)	0.015 (3)	0.053 (3)	0.087 (4)
O2	0.087 (3)	0.059 (3)	0.144 (5)	−0.029 (3)	−0.016 (3)	0.035 (3)
N1	0.057 (3)	0.049 (3)	0.052 (2)	0.000 (2)	0.012 (2)	0.013 (2)
C1	0.061 (4)	0.067 (4)	0.065 (4)	−0.010 (3)	0.015 (3)	0.028 (3)
C2	0.100 (6)	0.123 (7)	0.058 (4)	−0.002 (5)	0.010 (4)	0.011 (4)
C3	0.123 (8)	0.145 (10)	0.079 (6)	−0.039 (8)	−0.016 (6)	0.010 (6)
C4	0.077 (6)	0.138 (9)	0.121 (8)	−0.020 (6)	−0.010 (6)	0.051 (7)
C5	0.076 (6)	0.116 (7)	0.139 (8)	0.024 (5)	0.025 (6)	0.041 (7)
C6	0.072 (5)	0.077 (5)	0.096 (5)	0.011 (4)	0.009 (4)	0.019 (4)
C7	0.064 (4)	0.051 (3)	0.059 (3)	−0.005 (3)	0.023 (3)	−0.008 (3)
C8	0.070 (4)	0.053 (3)	0.039 (3)	−0.007 (3)	0.020 (2)	−0.002 (2)
C9	0.047 (3)	0.052 (3)	0.034 (2)	−0.002 (2)	0.005 (2)	−0.001 (2)
C10	0.066 (4)	0.050 (3)	0.061 (3)	0.006 (3)	0.007 (3)	0.005 (3)
C11	0.066 (4)	0.066 (4)	0.095 (5)	0.014 (3)	0.014 (4)	−0.021 (4)
C12	0.071 (4)	0.106 (6)	0.073 (4)	0.003 (4)	0.028 (4)	−0.036 (4)
C13	0.062 (4)	0.104 (5)	0.037 (3)	−0.001 (4)	0.013 (3)	−0.002 (3)
C14	0.043 (3)	0.057 (3)	0.038 (2)	−0.003 (2)	0.009 (2)	0.004 (2)
C15	0.079 (3)	0.074 (5)	0.110 (6)	−0.007 (4)	0.039 (4)	−0.026 (4)
C16	0.134 (5)	0.073 (4)	0.051 (3)	−0.026 (4)	0.038 (4)	0.001 (3)

Geometric parameters (Å, º) top

Cl1—C15	1.772 (4)	C7—C8	1.359 (8)
Br1—C16	1.9114 (11)	C7—C15	1.481 (9)
Br1A—C16	1.9084 (11)	C8—C9	1.415 (8)
S1—O2	1.411 (6)	C8—C16	1.489 (7)
S1—O1	1.415 (6)	C9—C10	1.381 (8)
S1—N1	1.659 (4)	C9—C14	1.390 (7)
S1—C1	1.737 (6)	C10—C11	1.371 (7)
N1—C14	1.417 (7)	C10—H10	0.9300
N1—C7	1.417 (7)	C11—C12	1.375 (8)
C1—C2	1.380 (8)	C11—H11	0.9300
C1—C6	1.386 (10)	C12—C13	1.372 (10)
C2—C3	1.396 (8)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.387 (8)
C3—C4	1.379 (9)	C13—H13	0.9300
C3—H3	0.9300	C15—H15A	0.9700
C4—C5	1.371 (9)	C15—H15B	0.9700
C4—H4	0.9300	C16—H16A	0.9700
C5—C6	1.371 (12)	C16—H16B	0.9700
C5—H5	0.9300	C16—H16C	0.9700
C6—H6	0.9300	C16—H16D	0.9700

O2—S1—O1	119.3 (4)	C9—C10—H10	120.6
O2—S1—N1	107.2 (3)	C10—C11—C12	120.3 (6)
O1—S1—N1	105.7 (3)	C10—C11—H11	119.9
O2—S1—C1	108.5 (3)	C12—C11—H11	119.9
O1—S1—C1	109.1 (4)	C13—C12—C11	122.5 (6)
N1—S1—C1	106.2 (3)	C13—C12—H12	118.8
C14—N1—C7	108.0 (4)	C11—C12—H12	118.8
C14—N1—S1	125.7 (4)	C12—C13—C14	117.1 (6)
C7—N1—S1	126.3 (4)	C12—C13—H13	121.4
C2—C1—C6	120.8 (7)	C14—C13—H13	121.4
C2—C1—S1	119.9 (6)	C13—C14—C9	120.9 (5)
C6—C1—S1	119.3 (5)	C13—C14—N1	131.9 (5)
C1—C2—C3	119.3 (8)	C9—C14—N1	107.2 (4)
C1—C2—H2	120.4	C7—C15—Cl1	111.8 (4)
C3—C2—H2	120.4	C7—C15—H15A	109.3
C4—C3—C2	119.1 (9)	Cl1—C15—H15A	109.3
C4—C3—H3	120.4	C7—C15—H15B	109.3
C2—C3—H3	120.4	Cl1—C15—H15B	109.3
C5—C4—C3	121.2 (9)	H15A—C15—H15B	107.9
C5—C4—H4	119.4	C8—C16—Br1A	113.8 (4)
C3—C4—H4	119.4	C8—C16—Br1	112.0 (4)
C6—C5—C4	120.1 (9)	C8—C16—H16A	109.2
C6—C5—H5	119.9	Br1A—C16—H16A	97.1
C4—C5—H5	119.9	Br1—C16—H16A	109.2
C5—C6—C1	119.5 (8)	C8—C16—H16B	109.2
C5—C6—H6	120.3	Br1A—C16—H16B	118.6
C1—C6—H6	120.3	Br1—C16—H16B	109.2
C8—C7—N1	107.6 (5)	H16A—C16—H16B	107.9
C8—C7—C15	128.1 (6)	C8—C16—H16C	108.4
N1—C7—C15	124.2 (6)	Br1A—C16—H16C	94.7
C7—C8—C9	109.4 (5)	Br1—C16—H16C	107.0
C7—C8—C16	123.8 (6)	H16B—C16—H16C	111.0
C9—C8—C16	126.7 (5)	C8—C16—H16D	110.3
C10—C9—C14	120.5 (5)	Br1A—C16—H16D	119.9
C10—C9—C8	131.7 (5)	Br1—C16—H16D	110.9
C14—C9—C8	107.8 (5)	H16A—C16—H16D	104.9
C11—C10—C9	118.7 (5)	H16C—C16—H16D	108.0
C11—C10—H10	120.6

O2—S1—N1—C14	146.0 (5)	C15—C7—C8—C16	7.1 (9)
O1—S1—N1—C14	17.8 (6)	C7—C8—C9—C10	179.3 (6)
C1—S1—N1—C14	−98.1 (5)	C16—C8—C9—C10	−2.1 (10)
O2—S1—N1—C7	−33.4 (6)	C7—C8—C9—C14	−0.3 (6)
O1—S1—N1—C7	−161.6 (5)	C16—C8—C9—C14	178.3 (5)
C1—S1—N1—C7	82.5 (5)	C14—C9—C10—C11	−0.2 (8)
O2—S1—C1—C2	−167.5 (6)	C8—C9—C10—C11	−179.8 (6)
O1—S1—C1—C2	−36.0 (6)	C9—C10—C11—C12	−0.4 (10)
N1—S1—C1—C2	77.6 (6)	C10—C11—C12—C13	0.3 (11)
O2—S1—C1—C6	11.3 (6)	C11—C12—C13—C14	0.4 (10)
O1—S1—C1—C6	142.8 (5)	C12—C13—C14—C9	−0.9 (8)
N1—S1—C1—C6	−103.7 (5)	C12—C13—C14—N1	−179.4 (6)
C6—C1—C2—C3	−0.2 (11)	C10—C9—C14—C13	0.9 (8)
S1—C1—C2—C3	178.6 (7)	C8—C9—C14—C13	−179.4 (5)
C1—C2—C3—C4	−0.5 (15)	C10—C9—C14—N1	179.7 (5)
C2—C3—C4—C5	1.1 (17)	C8—C9—C14—N1	−0.6 (6)
C3—C4—C5—C6	−1.0 (16)	C7—N1—C14—C13	179.9 (6)
C4—C5—C6—C1	0.3 (13)	S1—N1—C14—C13	0.4 (8)
C2—C1—C6—C5	0.2 (11)	C7—N1—C14—C9	1.3 (6)
S1—C1—C6—C5	−178.5 (6)	S1—N1—C14—C9	−178.2 (4)
C14—N1—C7—C8	−1.5 (6)	C8—C7—C15—Cl1	76.0 (8)
S1—N1—C7—C8	178.0 (4)	N1—C7—C15—Cl1	−98.7 (7)
C14—N1—C7—C15	174.1 (5)	C7—C8—C16—Br1A	−112.1 (6)
S1—N1—C7—C15	−6.4 (8)	C9—C8—C16—Br1A	69.5 (8)
N1—C7—C8—C9	1.1 (6)	C7—C8—C16—Br1	−98.2 (7)
C15—C7—C8—C9	−174.3 (5)	C9—C8—C16—Br1	83.4 (8)
N1—C7—C8—C16	−177.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.51	2.877 (9)	104
C13—H13···O1	0.93	2.31	2.873 (10)	118
C15—H15B···O2	0.97	2.17	2.939 (10)	136

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃BrClNO₂S
M_r	398.69
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	11.8501 (9), 16.3525 (13), 8.5793 (6)
β (°)	108.766 (3)
V (Å³)	1574.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.92
Crystal size (mm)	0.16 × 0.14 × 0.14

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.559, 0.665
No. of measured, independent and observed [I > 2σ(I)] reflections	14367, 2770, 1822
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.231, 1.06
No. of reflections	2770
No. of parameters	209
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.92

Computer programs: APEX2 (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2	0.93	2.51	2.877 (9)	104
C13—H13···O1	0.93	2.31	2.873 (10)	118
C15—H15B···O2	0.97	2.17	2.939 (10)	136

Acknowledgements

The authors acknowledge the Sophisticated Analytical Instrument Facility, Indian Institute of Technology, Madras, for the data collection.

References

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