4-(3-Chloro-2,2-dimethyl­propanamido)­benzene­sulfonamide

Yalçın, Ş.P.; Akkurt, M.; Durgun, M.; Türkkan, B.; Türkmen, H.

doi:10.1107/S1600536812046806

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3430

doi:10.1107/S1600536812046806

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4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide

Şerife Pınar Yalçın,^a,^b Mehmet Akkurt,^c ^* Mustafa Durgun,^d Baki Türkkan ^d and Hasan Türkmen ^d

^aDepartment of Physics, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey, ^bCentral Research Lab, Harran University, Osmanbey Campus, 63300 Şanlıurfa, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Chemistry, Faculty of Arts and Sciences, Harran University, 63300 Şanlıurfa, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 8 November 2012; accepted 14 November 2012; online 24 November 2012)

In the title compound, C₁₁H₁₅ClN₂O₃S, the 3-chloro-2,2-dimethylpropanamide and sulfonamide substituents are arranged on opposite sides of the benzene ring plane. In the crystal, molecules are linked by N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the antibacterial, antimicrobial and antiglaucoma activity of sulfonamides and their derivatives and for their physical properties and pharmacological applications, see: Poulsen et al. (2005 ); Supuran & Scozzafava (2000 ). For related structures, see: Akkurt et al. (2010 ); Idemudia et al. (2012 ); Asiri et al. (2012 ). For the synthesis, see: Türkmen et al. (2011 ).

Experimental

Crystal data

C₁₁H₁₅ClN₂O₃S
M_r = 290.77
Monoclinic, P 2₁ /c
a = 20.4359 (11) Å
b = 7.2437 (4) Å
c = 9.4693 (5) Å
β = 98.222 (3)°
V = 1387.35 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.43 mm⁻¹
T = 294 K
0.31 × 0.14 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: refined from ΔF (XABS2; Parkin et al., 1995 ) T_min = 0.931, T_max = 0.946
4240 measured reflections
4240 independent reflections
2054 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.231
S = 1.02
4240 reflections
175 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1—H1N⋯O1ⁱⁱ	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1—H2N⋯O1ⁱⁱⁱ	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2—H3N⋯O3^iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C11—H11B⋯O3^iv	0.97	2.44	3.391 (5)	166
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812046806/sj5282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812046806/sj5282Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812046806/sj5282Isup3.cml

checkCIF report

Comment top

Sulfonamides are of interest because of their unique biological properties. They are known inhibitors of the carbonic anhydrase enzyme, currently used for the treatment of glaucoma in clinical medicine (Poulsen et al., 2005; Supuran & Scozzafava, 2000). The design and development of new sulfanilamide derivatives can help determine any structural requirements for improved biological activity. In this study, we have prepared and determined the crystal structure of 4-(3-Chloro-2,2-dimethylpropanoylamino)-benzenesulfonamide (I).

In Fig. 1, the molecular structure of the title compound is not planar. In the 3-chloro-2,2-dimethylpropanamide moiety of (I), the N2—C7—C8—C9, N2—C7—C8—C10 and N2—C7—C8—C11 torsion angles are 178.6 (4), 57.2 (5) and -59.4 (5) °, respectively. The values of the bond lengths and bond angles in (I) are within the normal range and are comparable to those previously reported for the related structures (Akkurt et al., 2010; Idemudia et al., 2012; Asiri et al., 2012). The crystal structure is stabilized by intermolecular N—H···O and C—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the antibacterial, antimicrobial and antiglaucoma activity of sulfonamides and their derivatives and for their physical properties and pharmacological applications, see: Poulsen et al. (2005); Supuran & Scozzafava (2000). For related structures, see: Akkurt et al. (2010); Idemudia et al. (2012); Asiri et al. (2012). For the synthesis, see: Türkmen et al. (2011).

Experimental top

Nucleophilic acyl substitution of 3-chloro-2,2-dimethyl-propanoylchloride with sulfanilamide gave the title compound as described previously (Türkmen et al., 2011). Crystals suitable for X-ray diffraction studies were grown by slow evaporation of an ethanol, chloroform, dichloromethane (4/3/3 v/v) solution of the product.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. Packing of the title compound viewed along the b axis with N—H···O and C—H···O hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonding are omitted for clarity.

4-(3-Chloro-2,2-dimethylpropanamido)benzenesulfonamide top

Crystal data top

C₁₁H₁₅ClN₂O₃S	F(000) = 608
M_r = 290.77	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5710 reflections
a = 20.4359 (11) Å	θ = 2.5–30.5°
b = 7.2437 (4) Å	µ = 0.43 mm⁻¹
c = 9.4693 (5) Å	T = 294 K
β = 98.222 (3)°	Needle, white
V = 1387.35 (13) Å³	0.31 × 0.14 × 0.13 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4240 independent reflections
Radiation source: Sealed Tube	2054 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.000
Detector resolution: 10.0000 pixels mm^-1	θ_max = 30.6°, θ_min = 3.0°
ω scans	h = −29→28
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	k = 0→10
T_min = 0.931, T_max = 0.946	l = 0→13
4240 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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0751P)² + 1.0033P] where P = (F_o² + 2F_c²)/3
4240 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.36 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₁H₁₅ClN₂O₃S	V = 1387.35 (13) Å³
M_r = 290.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 20.4359 (11) Å	µ = 0.43 mm⁻¹
b = 7.2437 (4) Å	T = 294 K
c = 9.4693 (5) Å	0.31 × 0.14 × 0.13 mm
β = 98.222 (3)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	4240 independent reflections
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	2054 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.946	R_int = 0.000
4240 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	2 restraints
wR(F²) = 0.231	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.36 e Å⁻³
4240 reflections	Δρ_min = −0.33 e Å⁻³
175 parameters

Special details top

Experimental. Absorption correction: (XABS2; Parkin et al., 1995) Cubic fit to sin(theta)/lambda - 24 parameters

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
Cl1	0.05415 (8)	0.1450 (2)	0.13028 (15)	0.1040 (6)
S1	0.43958 (5)	−0.22940 (14)	0.07872 (10)	0.0540 (3)
O1	0.45415 (14)	−0.1736 (4)	−0.0593 (3)	0.0634 (10)
O2	0.42131 (15)	−0.4163 (4)	0.1004 (3)	0.0684 (11)
O3	0.19397 (15)	0.3907 (4)	0.0227 (3)	0.0689 (10)
N1	0.50493 (18)	−0.1856 (5)	0.1885 (3)	0.0592 (11)
N2	0.22555 (18)	0.2516 (5)	0.2354 (4)	0.0640 (13)
C1	0.37522 (19)	−0.0863 (6)	0.1199 (4)	0.0550 (14)
C2	0.3682 (2)	0.0917 (6)	0.0669 (4)	0.0603 (14)
C3	0.3193 (2)	0.2057 (6)	0.1041 (4)	0.0628 (17)
C4	0.2770 (2)	0.1406 (6)	0.1935 (4)	0.0579 (14)
C5	0.2852 (2)	−0.0344 (7)	0.2500 (4)	0.0691 (17)
C6	0.3339 (2)	−0.1493 (7)	0.2132 (4)	0.0675 (16)
C7	0.1859 (2)	0.3629 (6)	0.1465 (4)	0.0563 (14)
C8	0.1294 (2)	0.4544 (6)	0.2119 (4)	0.0643 (16)
C9	0.0901 (3)	0.5785 (8)	0.1019 (6)	0.102 (3)
C10	0.1581 (3)	0.5664 (8)	0.3447 (6)	0.102 (3)
C11	0.0849 (2)	0.3082 (7)	0.2637 (5)	0.0727 (18)
H1N	0.519 (3)	−0.074 (3)	0.174 (6)	0.1230*
H2	0.39660	0.13480	0.00580	0.0720*
H2N	0.500 (3)	−0.209 (8)	0.277 (2)	0.1230*
H3	0.31500	0.32570	0.06900	0.0750*
H3N	0.213 (3)	0.216 (8)	0.320 (6)	0.1230*
H5	0.25770	−0.07550	0.31350	0.0830*
H6	0.33890	−0.26790	0.25080	0.0810*
H9A	0.11770	0.67740	0.07780	0.1520*
H9B	0.05290	0.62860	0.14050	0.1520*
H9C	0.07470	0.50810	0.01780	0.1520*
H10A	0.18810	0.65780	0.31830	0.1530*
H10B	0.18120	0.48500	0.41480	0.1530*
H10C	0.12270	0.62620	0.38370	0.1530*
H11A	0.04780	0.36890	0.29760	0.0870*
H11B	0.10950	0.24310	0.34380	0.0870*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1001 (11)	0.1304 (13)	0.0862 (9)	−0.0399 (9)	0.0299 (8)	−0.0167 (8)
S1	0.0632 (6)	0.0599 (6)	0.0404 (5)	−0.0007 (5)	0.0126 (4)	0.0005 (4)
O1	0.079 (2)	0.0732 (19)	0.0411 (14)	0.0032 (15)	0.0195 (13)	−0.0002 (12)
O2	0.083 (2)	0.0627 (18)	0.0608 (17)	−0.0105 (15)	0.0144 (15)	−0.0004 (14)
O3	0.0708 (19)	0.090 (2)	0.0481 (15)	0.0074 (16)	0.0166 (13)	0.0051 (14)
N1	0.063 (2)	0.068 (2)	0.0475 (18)	−0.0015 (17)	0.0115 (16)	0.0033 (16)
N2	0.063 (2)	0.084 (3)	0.0473 (18)	0.0104 (19)	0.0163 (16)	0.0035 (18)
C1	0.058 (2)	0.066 (3)	0.0420 (19)	−0.0019 (19)	0.0104 (16)	0.0019 (17)
C2	0.061 (2)	0.070 (3)	0.053 (2)	−0.001 (2)	0.0190 (19)	0.008 (2)
C3	0.063 (3)	0.065 (3)	0.064 (3)	0.003 (2)	0.021 (2)	0.008 (2)
C4	0.056 (2)	0.075 (3)	0.044 (2)	0.001 (2)	0.0119 (17)	0.0023 (19)
C5	0.067 (3)	0.086 (3)	0.059 (3)	0.003 (2)	0.025 (2)	0.015 (2)
C6	0.067 (3)	0.079 (3)	0.059 (2)	0.008 (2)	0.018 (2)	0.017 (2)
C7	0.058 (2)	0.069 (3)	0.044 (2)	−0.003 (2)	0.0143 (17)	0.0006 (18)
C8	0.074 (3)	0.070 (3)	0.053 (2)	0.008 (2)	0.023 (2)	0.002 (2)
C9	0.113 (5)	0.104 (4)	0.098 (4)	0.042 (4)	0.048 (3)	0.032 (3)
C10	0.125 (5)	0.090 (4)	0.097 (4)	−0.007 (3)	0.035 (4)	−0.030 (3)
C11	0.073 (3)	0.095 (4)	0.054 (2)	0.008 (3)	0.023 (2)	0.002 (2)

Geometric parameters (Å, º) top

Cl1—C11	1.778 (5)	C7—C8	1.536 (6)
S1—O1	1.439 (3)	C8—C9	1.516 (7)
S1—O2	1.427 (3)	C8—C10	1.540 (7)
S1—N1	1.602 (4)	C8—C11	1.522 (6)
S1—C1	1.762 (4)	C2—H2	0.9300
O3—C7	1.224 (5)	C3—H3	0.9300
N2—C4	1.424 (6)	C5—H5	0.9300
N2—C7	1.349 (5)	C6—H6	0.9300
N1—H1N	0.88 (3)	C9—H9A	0.9600
N1—H2N	0.88 (2)	C9—H9B	0.9600
N2—H3N	0.91 (6)	C9—H9C	0.9600
C1—C2	1.384 (6)	C10—H10A	0.9600
C1—C6	1.384 (6)	C10—H10B	0.9600
C2—C3	1.380 (6)	C10—H10C	0.9600
C3—C4	1.377 (6)	C11—H11A	0.9700
C4—C5	1.377 (6)	C11—H11B	0.9700
C5—C6	1.380 (6)

O1—S1—O2	119.30 (17)	C9—C8—C10	110.6 (4)
O1—S1—N1	105.79 (17)	C9—C8—C11	110.6 (4)
O1—S1—C1	107.08 (18)	Cl1—C11—C8	113.6 (3)
O2—S1—N1	107.79 (18)	C1—C2—H2	120.00
O2—S1—C1	107.90 (19)	C3—C2—H2	120.00
N1—S1—C1	108.62 (19)	C2—C3—H3	120.00
C4—N2—C7	124.4 (4)	C4—C3—H3	120.00
H1N—N1—H2N	115 (5)	C4—C5—H5	120.00
S1—N1—H1N	110 (4)	C6—C5—H5	120.00
S1—N1—H2N	113 (4)	C1—C6—H6	120.00
C4—N2—H3N	113 (4)	C5—C6—H6	120.00
C7—N2—H3N	120 (4)	C8—C9—H9A	110.00
S1—C1—C2	120.7 (3)	C8—C9—H9B	109.00
C2—C1—C6	119.9 (4)	C8—C9—H9C	109.00
S1—C1—C6	119.4 (3)	H9A—C9—H9B	109.00
C1—C2—C3	120.4 (4)	H9A—C9—H9C	109.00
C2—C3—C4	119.6 (4)	H9B—C9—H9C	109.00
N2—C4—C3	122.1 (4)	C8—C10—H10A	109.00
N2—C4—C5	117.7 (4)	C8—C10—H10B	109.00
C3—C4—C5	120.1 (4)	C8—C10—H10C	109.00
C4—C5—C6	120.6 (4)	H10A—C10—H10B	110.00
C1—C6—C5	119.4 (4)	H10A—C10—H10C	109.00
O3—C7—C8	121.8 (4)	H10B—C10—H10C	110.00
N2—C7—C8	115.2 (3)	Cl1—C11—H11A	109.00
O3—C7—N2	123.0 (4)	Cl1—C11—H11B	109.00
C10—C8—C11	106.2 (4)	C8—C11—H11A	109.00
C7—C8—C11	110.4 (4)	C8—C11—H11B	109.00
C7—C8—C9	109.5 (4)	H11A—C11—H11B	108.00
C7—C8—C10	109.6 (4)

O1—S1—C1—C2	−29.3 (4)	C2—C3—C4—N2	−179.9 (4)
O1—S1—C1—C6	154.6 (3)	C2—C3—C4—C5	2.7 (6)
O2—S1—C1—C2	−158.9 (3)	N2—C4—C5—C6	179.7 (4)
O2—S1—C1—C6	25.0 (4)	C3—C4—C5—C6	−2.8 (6)
N1—S1—C1—C2	84.5 (4)	C4—C5—C6—C1	0.8 (6)
N1—S1—C1—C6	−91.6 (4)	O3—C7—C8—C9	−1.1 (6)
C7—N2—C4—C3	42.6 (6)	O3—C7—C8—C10	−122.6 (4)
C7—N2—C4—C5	−139.9 (4)	O3—C7—C8—C11	120.8 (4)
C4—N2—C7—O3	−6.2 (7)	N2—C7—C8—C9	178.6 (4)
C4—N2—C7—C8	174.1 (4)	N2—C7—C8—C10	57.2 (5)
S1—C1—C2—C3	−177.4 (3)	N2—C7—C8—C11	−59.4 (5)
C6—C1—C2—C3	−1.4 (6)	C7—C8—C11—Cl1	−54.2 (4)
S1—C1—C6—C5	177.4 (3)	C9—C8—C11—Cl1	67.1 (4)
C2—C1—C6—C5	1.3 (6)	C10—C8—C11—Cl1	−172.9 (3)
C1—C2—C3—C4	−0.6 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1—H1N···O1ⁱⁱ	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1—H2N···O1ⁱⁱⁱ	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2—H3N···O3^iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C3—H3···O3	0.93	2.49	2.896 (5)	106
C6—H6···O2	0.93	2.59	2.936 (5)	103
C11—H11B···O3^iv	0.97	2.44	3.391 (5)	166

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₅ClN₂O₃S
M_r	290.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	20.4359 (11), 7.2437 (4), 9.4693 (5)
β (°)	98.222 (3)
V (Å³)	1387.35 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.43
Crystal size (mm)	0.31 × 0.14 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)
T_min, T_max	0.931, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	4240, 4240, 2054
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.231, 1.02
No. of reflections	4240
No. of parameters	175
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.33

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.88 (3)	2.57 (5)	3.035 (4)	114 (4)
N1—H1N···O1ⁱⁱ	0.88 (3)	2.21 (4)	3.043 (5)	160 (5)
N1—H2N···O1ⁱⁱⁱ	0.88 (2)	2.10 (4)	2.921 (4)	155 (5)
N2—H3N···O3^iv	0.91 (6)	2.16 (6)	3.063 (5)	173 (5)
C11—H11B···O3^iv	0.97	2.44	3.391 (5)	166

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

Acknowledgements

The authors thank the Unit of Scientific Research Projects of Harran University, Turkey for a research grant (HUBAK project Nos. 874 and 1136).

References

Akkurt, M., Yalçın, Ş. P., Türkmen, H. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1559–o1560. Web of Science 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
Asiri, A. M., Faidallah, H. M., Alamry, K. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2258–o2259. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Idemudia, O. G., Sadimenko, A. P., Afolayan, A. J. & Hosten, E. C. (2012). Acta Cryst. E68, o1599. CSD CrossRef IUCr Journals Google Scholar
Parkin, S., Moezzi, B. & Hope, H. (1995). J. Appl. Cryst. 28, 53–56. CrossRef CAS Web of Science IUCr Journals Google Scholar
Poulsen, S., Bornaghi, L. F. & Healy, P. C. (2005). Bioorg. Med. Chem. Lett. 15, 5429–5433. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA. 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
Supuran, C. T. & Scozzafava, A. (2000). Exp. Opin. Ther. Pat. 10, 575–600. CrossRef CAS Google Scholar
Türkmen, H., Zengin, G. & Buyukkircali, B. (2011). Bioorg. Chem. 39 114–119. Web of Science PubMed Google Scholar