2,4-Dichloro-N-phenethyl­benzene­sulfonamide

Babu, C.S.M.; Kavitha, H.P.; Kavipriya, R.; Vennila, J.P.; Manivannan, V.

doi:10.1107/S1600536809010927

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o921

doi:10.1107/S1600536809010927

Open

access

2,4-Dichloro-N-phenethylbenzenesulfonamide

C. Suneel Manohar Babu,^a Helen P. Kavitha,^b R. Kavipriya,^b Jasmine P. Vennila ^c and V. Manivannan ^d ^*

^aNicholas Piramal Research Centre, Nicholas Piramal India Limited, Mumbai 400 063, India, ^bDepartment of Chemistry, SRM University, Ramapuram, Chennai 600 089, India, ^cDepartment of Physics, Panimalar Institute of Technology, Chennai 600 095, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, India
^*Correspondence e-mail: manivan_1999@yahoo.com

(Received 18 March 2009; accepted 24 March 2009; online 31 March 2009)

In the title compound, C₁₄H₁₃Cl₂NO₂S, the dihedral angle between the phenyl ring and the benzene ring is 69.94 (9)°. Two short intramolecular C—H⋯O contacts occur and a weak intermolecular C—H⋯π interaction is seen in the crystal.

Related literature

For the biological activity of sulfonamides, see: Gadad et al. (2000 ); Misra et al. (1982 ); Zani & Vicini (1998 ); Maren (1976 ); Supuran et al. (1998 ); Renzi et al. (2000 ); Li et al. (1995 ); Yoshino et al. (1992 ). For related structures, see: Zhang et al. (2006 ); Andrighetti-Fröhner et al. (2007 ); For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃Cl₂NO₂S
M_r = 330.21
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.5618 (5) Å
b = 10.9915 (8) Å
c = 25.045 (2) Å
V = 1531.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 295 K
0.20 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.896, T_max = 0.936
10930 measured reflections
3511 independent reflections
2955 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.104
S = 1.05
3511 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1455 Friedel pairs
Flack parameter: 0.04 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O2	0.97	2.51	2.953 (3)	108
C14—H14⋯O2	0.93	2.44	2.848 (3)	106
C6—H6⋯Cg1ⁱ	0.93	2.96	3.694 (3)	137
Symmetry code: (i) $[-x-1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010927/is2402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010927/is2402Isup2.hkl

checkCIF report

Comment top

Sulfonamides have a variety of biological activities such as antibacterial (Gadad et al., 2000; Misra et al., 1982; Zani & Vicini, 1998), insulin releasing (Maren, 1976), carbonic anhydrase inhibitory (Supuran et al., 1998; Renzi et al., 2000), anti-inflammatory (Li et al., 1995) and antitumor (Yoshino et al., 1992) activities.

The geometric parameters in the title compound, (I), agree with the reported values of similar structure (Zhang et al., 2006; Andrighetti-Fröhner et al., 2007). The dihedral angle between the phenyl ring (C9—C14) and benzene ring (C1—C6) is 69.94 (9)°. The geometry around the S1 atom is distorted from a regular tetrahedron, with the largest deviations observed for O—S—O [O1—S1—O2 118.92 (14)°] and O—S—N [O1—S1—N1 107.87 (14) °] angles. The widening of the angles may be due to repulsive interactions between the two short S=O bonds.

The crystal structure is stabilized by weak intramolecular C—H···O interaction. The C8—H8B···O2 and C14—H14···O2 interactions each generate an S(5) graph set motif, and C8—H8B···O2 and C14—H14···O2 interactions together constitute a pair of bifurcated acceptor bonds, generating an R₂¹(8) motif (Bernstein et al., 1995). The crystal packing is stabilized by a weak C—H···π (Table 1) interaction and a π–π interaction [Cg1···Cg2 (2 - x, 1/2 + y, 1/2 - z) distance of 4.3598 (18) Å; Cg1 and Cg2 are the centroids of rings C1—C6 and C9—C14, respectively].

Related literature top

For the biological activity of sulfonamides, see: Gadad et al. (2000); Misra et al. (1982); Zani & Vicini (1998); Maren (1976); Supuran et al. (1998); Renzi et al. (2000); Li et al. (1995); Yoshino et al. (1992). For related structures, see: Zhang et al. (2006); Andrighetti-Fröhner et al. (2007); For graph-set notation, see: Bernstein et al. (1995). Cg1 is the centroid of the C1–C6 ring.

Experimental top

About 1 g (8 mmol) of 2-phenylethyl amine is dissolved in 20 ml of dichloromethane. 1.3 g (16 mmol) of pyridine is added into the reaction mass. The above mixture is stirred for 5 min. To this, 2.41 g (9.8 mmol) of 2, 4-dichlorobenzene-1-sulfonyl chloride is added and heated to 35 - 40 ° C for 6 hrs. The reaction mass is then cooled to the room temperature and 20 ml of water is added to it. The aquous layer is separated. The organic layer is washed with 10% sodium chloride solution and dried over 2 g of anhydrous sodium sulfate. The excess solvent is removed under vacuum. The crude compound is purified through column chromatography using hexane and ethyl acetate as eluants.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.

2,4-Dichloro-N-phenethylbenzenesulfonamide top

Crystal data top

C₁₄H₁₃Cl₂NO₂S	F(000) = 680
M_r = 330.21	D_x = 1.433 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	θ = 1.6–27.6°
a = 5.5618 (5) Å	µ = 0.56 mm⁻¹
b = 10.9915 (8) Å	T = 295 K
c = 25.045 (2) Å	Block, white
V = 1531.0 (2) Å³	0.20 × 0.18 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3511 independent reflections
Radiation source: fine-focus sealed tube	2955 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and ϕ scans	θ_max = 27.6°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.896, T_max = 0.936	k = −8→13
10930 measured reflections	l = −32→32

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0546P)² + 0.264P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3511 reflections	Δρ_max = 0.27 e Å⁻³
181 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1455 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.04 (8)

Crystal data top

C₁₄H₁₃Cl₂NO₂S	V = 1531.0 (2) Å³
M_r = 330.21	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.5618 (5) Å	µ = 0.56 mm⁻¹
b = 10.9915 (8) Å	T = 295 K
c = 25.045 (2) Å	0.20 × 0.18 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3511 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2955 reflections with I > 2σ(I)
T_min = 0.896, T_max = 0.936	R_int = 0.026
10930 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.104	Δρ_max = 0.27 e Å⁻³
S = 1.05	Δρ_min = −0.24 e Å⁻³
3511 reflections	Absolute structure: Flack (1983), 1455 Friedel pairs
181 parameters	Absolute structure parameter: 0.04 (8)
0 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
S1	0.77658 (10)	0.02339 (6)	0.22502 (2)	0.04851 (16)
Cl2	1.21110 (11)	−0.02059 (7)	0.30970 (3)	0.06133 (19)
Cl1	0.8648 (3)	0.32987 (9)	0.43460 (4)	0.1235 (5)
C1	1.1601 (5)	0.2812 (2)	0.07918 (9)	0.0492 (6)
C2	1.3486 (6)	0.3577 (3)	0.08766 (14)	0.0721 (9)
H2	1.4664	0.3368	0.1123	0.087*
C3	1.3671 (7)	0.4658 (4)	0.06019 (18)	0.0914 (11)
H3	1.4972	0.5170	0.0664	0.110*
C4	1.1958 (8)	0.4980 (3)	0.02405 (14)	0.0816 (10)
H4	1.2091	0.5707	0.0053	0.098*
C5	1.0062 (7)	0.4235 (3)	0.01560 (11)	0.0727 (9)
H5	0.8878	0.4457	−0.0087	0.087*
C6	0.9872 (5)	0.3153 (3)	0.04272 (10)	0.0578 (7)
H6	0.8564	0.2646	0.0364	0.069*
C7	1.1389 (6)	0.1609 (3)	0.10805 (10)	0.0649 (8)
H7A	1.0433	0.1056	0.0866	0.078*
H7B	1.2979	0.1257	0.1119	0.078*
C8	1.0261 (5)	0.1724 (2)	0.16216 (9)	0.0541 (6)
H8A	1.1250	0.2242	0.1846	0.065*
H8B	0.8690	0.2100	0.1588	0.065*
C9	0.8116 (4)	0.1116 (2)	0.28395 (9)	0.0413 (5)
C10	0.9959 (5)	0.0905 (2)	0.32017 (9)	0.0464 (5)
C11	1.0144 (6)	0.1593 (3)	0.36615 (11)	0.0625 (7)
H11	1.1390	0.1460	0.3902	0.075*
C12	0.8444 (8)	0.2484 (2)	0.37570 (12)	0.0683 (9)
C13	0.6653 (7)	0.2725 (3)	0.34033 (12)	0.0649 (8)
H13	0.5550	0.3341	0.3472	0.078*
C14	0.6490 (5)	0.2044 (2)	0.29421 (11)	0.0527 (6)
H14	0.5277	0.2209	0.2697	0.063*
O1	0.7876 (4)	−0.10180 (17)	0.23927 (8)	0.0660 (5)
O2	0.5657 (3)	0.0685 (2)	0.19918 (7)	0.0652 (5)
N1	1.0011 (4)	0.05205 (19)	0.18713 (7)	0.0525 (5)
H1	1.1075	−0.0032	0.1813	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0474 (3)	0.0475 (3)	0.0506 (3)	−0.0037 (3)	−0.0090 (2)	0.0003 (3)
Cl2	0.0503 (3)	0.0567 (4)	0.0770 (4)	0.0050 (3)	−0.0114 (3)	0.0147 (3)
Cl1	0.2342 (16)	0.0666 (5)	0.0696 (5)	0.0090 (8)	−0.0224 (7)	−0.0190 (4)
C1	0.0556 (14)	0.0533 (14)	0.0387 (11)	0.0056 (12)	0.0057 (10)	−0.0047 (10)
C2	0.0584 (17)	0.077 (2)	0.081 (2)	0.0036 (16)	−0.0144 (15)	−0.0071 (16)
C3	0.071 (2)	0.077 (2)	0.127 (3)	−0.027 (2)	0.006 (2)	−0.016 (2)
C4	0.112 (3)	0.0536 (18)	0.079 (2)	−0.0024 (19)	0.033 (2)	0.0067 (15)
C5	0.088 (2)	0.075 (2)	0.0555 (16)	0.015 (2)	−0.0057 (16)	0.0062 (14)
C6	0.0588 (16)	0.0628 (17)	0.0519 (13)	−0.0051 (14)	−0.0074 (12)	0.0016 (12)
C7	0.089 (2)	0.0573 (17)	0.0487 (14)	0.0127 (16)	0.0044 (14)	0.0025 (12)
C8	0.0655 (16)	0.0460 (14)	0.0509 (13)	0.0075 (13)	0.0051 (12)	−0.0006 (11)
C9	0.0406 (11)	0.0402 (12)	0.0431 (11)	−0.0074 (9)	−0.0018 (9)	0.0066 (9)
C10	0.0468 (13)	0.0409 (13)	0.0514 (12)	−0.0059 (10)	−0.0047 (11)	0.0113 (10)
C11	0.083 (2)	0.0507 (16)	0.0538 (14)	−0.0166 (15)	−0.0199 (14)	0.0106 (12)
C12	0.111 (3)	0.0363 (14)	0.0576 (15)	−0.0069 (15)	−0.0049 (18)	0.0012 (11)
C13	0.084 (2)	0.0424 (15)	0.0684 (17)	0.0063 (14)	0.0066 (16)	0.0037 (13)
C14	0.0527 (14)	0.0469 (14)	0.0584 (14)	0.0022 (11)	0.0003 (11)	0.0085 (11)
O1	0.0804 (14)	0.0448 (10)	0.0729 (12)	−0.0147 (10)	−0.0121 (11)	0.0008 (8)
O2	0.0520 (10)	0.0814 (14)	0.0622 (11)	−0.0011 (9)	−0.0156 (9)	−0.0014 (10)
N1	0.0615 (13)	0.0455 (12)	0.0505 (11)	0.0137 (10)	0.0049 (10)	0.0022 (9)

Geometric parameters (Å, º) top

S1—O1	1.423 (2)	C6—H6	0.9300
S1—O2	1.429 (2)	C7—C8	1.499 (4)
S1—N1	1.600 (2)	C7—H7A	0.9700
S1—C9	1.777 (2)	C7—H7B	0.9700
Cl2—C10	1.730 (3)	C8—N1	1.470 (3)
Cl1—C12	1.730 (3)	C8—H8A	0.9700
C1—C2	1.361 (4)	C8—H8B	0.9700
C1—C6	1.378 (4)	C9—C14	1.387 (3)
C1—C7	1.512 (4)	C9—C10	1.388 (3)
C2—C3	1.376 (5)	C10—C11	1.382 (4)
C2—H2	0.9300	C11—C12	1.382 (5)
C3—C4	1.361 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.359 (5)
C4—C5	1.351 (5)	C13—C14	1.379 (4)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.374 (4)	C14—H14	0.9300
C5—H5	0.9300	N1—H1	0.8600

O1—S1—O2	119.00 (13)	H7A—C7—H7B	107.8
O1—S1—N1	107.80 (12)	N1—C8—C7	110.4 (2)
O2—S1—N1	107.69 (11)	N1—C8—H8A	109.6
O1—S1—C9	108.35 (11)	C7—C8—H8A	109.6
O2—S1—C9	106.06 (11)	N1—C8—H8B	109.6
N1—S1—C9	107.44 (11)	C7—C8—H8B	109.6
C2—C1—C6	118.2 (3)	H8A—C8—H8B	108.1
C2—C1—C7	121.8 (3)	C14—C9—C10	118.9 (2)
C6—C1—C7	120.0 (3)	C14—C9—S1	118.93 (18)
C1—C2—C3	120.9 (3)	C10—C9—S1	122.15 (19)
C1—C2—H2	119.6	C11—C10—C9	120.5 (3)
C3—C2—H2	119.6	C11—C10—Cl2	117.5 (2)
C4—C3—C2	120.3 (3)	C9—C10—Cl2	122.02 (19)
C4—C3—H3	119.8	C12—C11—C10	118.8 (3)
C2—C3—H3	119.8	C12—C11—H11	120.6
C5—C4—C3	119.5 (3)	C10—C11—H11	120.6
C5—C4—H4	120.2	C13—C12—C11	121.8 (3)
C3—C4—H4	120.2	C13—C12—Cl1	120.2 (3)
C4—C5—C6	120.5 (3)	C11—C12—Cl1	118.0 (3)
C4—C5—H5	119.8	C12—C13—C14	119.2 (3)
C6—C5—H5	119.8	C12—C13—H13	120.4
C5—C6—C1	120.6 (3)	C14—C13—H13	120.4
C5—C6—H6	119.7	C13—C14—C9	120.7 (3)
C1—C6—H6	119.7	C13—C14—H14	119.6
C8—C7—C1	113.0 (2)	C9—C14—H14	119.6
C8—C7—H7A	109.0	C8—N1—S1	120.22 (17)
C1—C7—H7A	109.0	C8—N1—H1	119.9
C8—C7—H7B	109.0	S1—N1—H1	119.9
C1—C7—H7B	109.0

C6—C1—C2—C3	−0.6 (5)	C14—C9—C10—C11	1.1 (3)
C7—C1—C2—C3	178.7 (3)	S1—C9—C10—C11	−178.63 (19)
C1—C2—C3—C4	0.2 (6)	C14—C9—C10—Cl2	−178.26 (18)
C2—C3—C4—C5	0.5 (6)	S1—C9—C10—Cl2	2.0 (3)
C3—C4—C5—C6	−0.8 (5)	C9—C10—C11—C12	0.9 (4)
C4—C5—C6—C1	0.4 (5)	Cl2—C10—C11—C12	−179.7 (2)
C2—C1—C6—C5	0.3 (4)	C10—C11—C12—C13	−2.3 (5)
C7—C1—C6—C5	−179.0 (3)	C10—C11—C12—Cl1	177.8 (2)
C2—C1—C7—C8	84.4 (4)	C11—C12—C13—C14	1.6 (5)
C6—C1—C7—C8	−96.4 (3)	Cl1—C12—C13—C14	−178.5 (2)
C1—C7—C8—N1	177.6 (2)	C12—C13—C14—C9	0.5 (4)
O1—S1—C9—C14	−130.6 (2)	C10—C9—C14—C13	−1.8 (4)
O2—S1—C9—C14	−1.7 (2)	S1—C9—C14—C13	177.9 (2)
N1—S1—C9—C14	113.21 (19)	C7—C8—N1—S1	−146.0 (2)
O1—S1—C9—C10	49.2 (2)	O1—S1—N1—C8	174.72 (19)
O2—S1—C9—C10	178.00 (18)	O2—S1—N1—C8	45.2 (2)
N1—S1—C9—C10	−67.0 (2)	C9—S1—N1—C8	−68.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2	0.97	2.51	2.953 (3)	108
C14—H14···O2	0.93	2.44	2.848 (3)	106
C6—H6···Cg1ⁱ	0.93	2.96	3.694 (3)	137

Symmetry code: (i) −x−1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃Cl₂NO₂S
M_r	330.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	5.5618 (5), 10.9915 (8), 25.045 (2)
V (Å³)	1531.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.20 × 0.18 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.896, 0.936
No. of measured, independent and observed [I > 2σ(I)] reflections	10930, 3511, 2955
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.104, 1.05
No. of reflections	3511
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24
Absolute structure	Flack (1983), 1455 Friedel pairs
Absolute structure parameter	0.04 (8)

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2	0.97	2.51	2.953 (3)	108
C14—H14···O2	0.93	2.44	2.848 (3)	106
C6—H6···Cg1ⁱ	0.93	2.96	3.694 (3)	137

Symmetry code: (i) −x−1, y+1/2, −z+1/2.

Acknowledgements

The authors acknowledge SAIF IIT, Chennai, for the data collection.

References

Andrighetti-Fröhner, C. R., Joussef, A. C., Simões, C. M. O., Nunes, R. J. & Bortoluzzi, A. J. (2007). Acta Cryst. E63, o3275–o3276. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Gadad, A. K., Mahajanshetti, C. S., Nimbalkar, S. & Raichurkar, A. (2000). Eur. J. Med. Chem. 35, 853–855. Web of Science CrossRef PubMed CAS Google Scholar
Li, J. J., Anderson, D., Burton, E. G., Cogburn, J. N., Collins, J. T., Garland, D. J., Gregory, S. A., Huang, H. C., Isakson, P. C., Koboldt, C. M., Logusch, E. W., Norton, M. B., Perkins, W. E., Reinhard, E. J., Seibert, K., Veenhuizem, A. W., Zang, Y. & Reitz, D. B. (1995). J. Med. Chem. 38, 4570–4570. CrossRef CAS PubMed Web of Science Google Scholar
Maren, T. H. (1976). Annu. Rev. Pharmacol. Toxicol. 16, 309–309. CrossRef CAS PubMed Web of Science Google Scholar
Misra, V. S., Saxena, V. K. & Srivastava, R. J. (1982). J. Indian Chem. Soc. 59, 781–781. CAS Google Scholar
Renzi, G., Scozzafava, A. & Supuran, C. T. (2000). Bioorg. Med. Chem. Lett. 10, 673–673. 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Supuran, C. T., Scozzafava, A., Jurca, B. C. & Iiies, M. A. (1998). Eur. J. Med. Chem. 33, 83–83. Web of Science CrossRef CAS Google Scholar
Yoshino, H., Ueda, N., Niijma, J., Sugumi, H., Kotake, Y., Koyanagi, N., Yoshimatsu, K., Asada, M., Watanabe, T., Nagasu, T., Tsukahara, K., Lijima, A. & Kitoh, K. (1992). J. Med. Chem. 35, 2496–2496. CrossRef PubMed CAS Web of Science Google Scholar
Zani, F. & Vicini, P. (1998). Arch. Pharm. 331, 219–219. CrossRef CAS Google Scholar
Zhang, X.-L., Yan, Y.-P., Ding, L. & Luo, L.-T. (2006). Acta Cryst. E62, o5809–o5810. Web of Science CSD CrossRef IUCr Journals Google Scholar