N,N-Bis(2-hy­droxy­eth­yl)-4-methyl­benzene­sulfonamide

Mushtaq, N.; Khan, I.U.; Yar, M.; Afzal, S.; Simpson, J.

doi:10.1107/S1600536812041682

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3142

doi:10.1107/S1600536812041682

Open

access

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide

Nafeesa Mushtaq,^a Islam Ullah Khan,^a ^* Muhammad Yar,^a Sadia Afzal ^a and Jim Simpson ^b

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, and ^bDepartment of Chemistry, University of Otago, PO Box 56, Dunedin 9054, New Zealand
^*Correspondence e-mail: iuklodhi@yahoo.com

(Received 11 August 2012; accepted 5 October 2012; online 20 October 2012)

In the title compound C₁₁H₁₇NO₄S, an intramolecular O—H⋯O hydrogen bond forms an S(8) ring and determines the conformation of the bis(2-hydroxyethyl) segment of the molecule, holding the two CH₂CH₂OH groups close to coplanar (r.m.s. deviation = 0.185 Å). In the crystal, O—H⋯O hydrogen bonds link the molecules into zigzag chains along the b axis. Weaker additional C—H⋯O and C—H⋯π contacts generate a three dimensional network, with molecules stacked along the b-axis direction.

Related literature

For pharmaceutical background to sulfonamides, see: Casini et al. (2002 ); Chambers & Jawetz (1998 ). For an alternative synthesis, see: Hori et al. (2011 ). For a related structure, see: Yoon et al. (2001 ). For standard bond lengths, see: Allen et al. (1987 ) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₁H₁₇NO₄S
M_r = 259.32
Orthorhombic, P b c a
a = 17.9308 (5) Å
b = 7.1881 (2) Å
c = 19.8333 (6) Å
V = 2556.28 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 296 K
0.16 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
3124 measured reflections
3124 independent reflections
2343 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.161
S = 0.99
3124 reflections
161 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3—H3O⋯O4ⁱ	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10—H10A⋯O1ⁱⁱ	0.97	2.61	3.361 (3)	135
C3—H3⋯Cg1ⁱⁱⁱ	0.93	2.78	3.522 (2)	138
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97, ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004 ), PLATON (Spek, 2009 ) and publCIF (Westrip 2010 ).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041682/nk2181sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041682/nk2181Isup2.hkl

checkCIF report

Comment top

Sulfonamides are an important class of drugs with antibacterial, diuretic, hypoglycemic, antithyroid and antitumor action (Casini et al., 2002). Certain sulfonamides are used in combination with other drugs as antimicrobial agents and this paved the way for an antibiotic revolution in medicine. Sulfonamides also act as anti-metabolites and compete for the enzyme involved in the production of folic acid (Chambers & Jawetz, 1998). Most sulfonamides behave as weak acids and binding to basic amino acids can occur. The crystal structure of a tritosylate of diethanolamine has been reported in which the three tosyl groups are separated from one another as much as possible, to minimize steric repulsion (Yoon et al., 2001). The promising pharmaceutical potential of sulfonamides has prompted us to synthesize and characterize diethanolamine derived sulfonamides. Diethanolamine (DEA) itself has skin irritant characteristics; however, when DEA is transformed into new materials, the resulting compounds may become pharmaceutically useful. We therefore synthesized N,N-bis(2-hydroxyethyl)-4-methylbenzenesulfonamide (N-tosyl diethanolamine) (1) and report its molecular and crystal structure here.

The molecular structure of (1) is shown in Fig. 1. The tolyl ring (C1···C6) is inclined at dihedral angles of 27.29 (0.16) ° and 37.78 (0.17) ° with respect to the N1/C8/C9 and N1/C10/C11 planes respectively. Bond distances (Allen et al., 1987) and angles within the molecule are normal and similar to those reported for N,N-bis(tosyloxyethyl)-p-toluenesulfonamide (Yoon et al., 2001). The nitrogen atom of the diethanolamine substituent is approximately sp³ hybridized with the geometry around the N1 atom close to pyramidal [C8—N1—S1 = 117.49 (14)°, C10—N1—S1 = 116.76 (14)° and C8—N1—C10 = 117.98 (18)°]. The two ethanol substituents are unsymmetrically oriented around the nitrogen atom with their conformations ultimately determined by an intramolecular O4—H4···O3 hydrogen bond that forms an S(8) ring (Bernstein et al., 1995).

In the crystal structure intermolecular O3—H3···O4 hydrogen bonds, Table 1, link molecules into zigzag chains along the b axis, Fig 2. C3—H3···π contacts, together with additional C10—H10A···O1 hydrogen bonds, further connect the chains to form a three-dimensional network structure, with molecules stacked along b, Fig 3.

Related literature top

For pharmaceutical background to sulfonamides, see: Casini et al. (2002); Chambers & Jawetz (1998). For an alternative synthesis, see: Hori et al. (2011). For a related structure, see: Yoon et al. (2001). For standard bond lengths, see: Allen et al. (1987) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Tosyl chloride (0.836 g, 4.4 mmol) was added to a flask containing diethanolamine (0.42 g, 4 mmol) dissolved in CH₂Cl₂. Pyridine was added as a base (0.35 g, 4.4 mmol) and the solution refluxed for 4 hrs. On completion of the reaction, the pyridine was removed in vacuo and the product purified by crystallization. White crystals were obtained with an overall yield of 77%; Rf 0.13 (1:1 hexane and ethyl acetate). M.P: 95–98 0 C; 1H NMR 500 MHz, CDCl₃: 7.70 (d, 2H), 7.33 (d, 2H), 3.87 (t, –CH₂OH, 4H), 3.23 (t, –CH₂N–, 4H), 2.43 (s, –CH₃, 3H). The synthesis of (1) has also been reported using triethylamine rather than pyridine (Hori et al., 2011).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip 2010).

Figures top

	Fig. 1. The molecular structure of (1) showing the atom numbering scheme with displacement ellipsoids drawn at the 50% probability level. The intramolecular hydrogen bond is drawn as an open dashed line.
	Fig. 2. Zigzag chains of molecules formed along b by intermolecular O—H···O hydrogen bonds, shown as dashed lines.
	Fig. 3. Overall packing for (1) viewed along the b axis with hydrogen bonds drawn as dashed lines.

N,N-Bis(2-hydroxyethyl)-4-methylbenzenesulfonamide top

Crystal data top

C₁₁H₁₇NO₄S	F(000) = 1104
M_r = 259.32	D_x = 1.348 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4787 reflections
a = 17.9308 (5) Å	θ = 2.3–27.7°
b = 7.1881 (2) Å	µ = 0.26 mm⁻¹
c = 19.8333 (6) Å	T = 296 K
V = 2556.28 (13) Å³	Block, colourless
Z = 8	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2343 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 28.3°, θ_min = 3.1°
ϕ and ω scans	h = 0→23
3124 measured reflections	k = 0→9
3124 independent reflections	l = 0→25

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0948P)² + 1.0844P] where P = (F_o² + 2F_c²)/3
3124 reflections	(Δ/σ)_max = 0.009
161 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₁H₁₇NO₄S	V = 2556.28 (13) Å³
M_r = 259.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.9308 (5) Å	µ = 0.26 mm⁻¹
b = 7.1881 (2) Å	T = 296 K
c = 19.8333 (6) Å	0.16 × 0.12 × 0.10 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2343 reflections with I > 2σ(I)
3124 measured reflections	R_int = 0.000
3124 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.45 e Å⁻³
3124 reflections	Δρ_min = −0.39 e Å⁻³
161 parameters

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
O1	0.20186 (10)	0.1722 (3)	0.09437 (9)	0.0733 (6)
O2	0.08536 (10)	0.0146 (2)	0.06009 (8)	0.0598 (4)
S1	0.13232 (3)	0.17523 (7)	0.05993 (3)	0.04344 (19)
C1	0.15067 (10)	0.2344 (3)	−0.02460 (10)	0.0382 (4)
C2	0.21585 (12)	0.3277 (3)	−0.04138 (12)	0.0501 (5)
H2	0.2511	0.3542	−0.0084	0.060*
C3	0.22799 (14)	0.3806 (3)	−0.10709 (13)	0.0575 (6)
H3	0.2716	0.4437	−0.1181	0.069*
C4	0.17630 (14)	0.3417 (3)	−0.15754 (12)	0.0529 (6)
C7	0.1893 (2)	0.4011 (5)	−0.22931 (15)	0.0846 (9)
H7A	0.2302	0.3318	−0.2478	0.127*
H7B	0.2008	0.5315	−0.2305	0.127*
H7C	0.1452	0.3778	−0.2554	0.127*
C5	0.11233 (13)	0.2452 (3)	−0.13986 (11)	0.0501 (5)
H5	0.0777	0.2156	−0.1731	0.060*
C6	0.09883 (11)	0.1920 (3)	−0.07401 (10)	0.0420 (4)
H6	0.0553	0.1284	−0.0630	0.050*
N1	0.08353 (9)	0.3445 (2)	0.09165 (9)	0.0429 (4)
C8	0.00254 (12)	0.3381 (3)	0.08243 (11)	0.0495 (5)
H8A	−0.0087	0.2717	0.0411	0.059*
H8B	−0.0162	0.4640	0.0777	0.059*
C9	−0.03700 (14)	0.2449 (4)	0.14009 (13)	0.0635 (7)
H9A	−0.0899	0.2359	0.1302	0.076*
H9B	−0.0177	0.1200	0.1460	0.076*
O3	−0.02636 (12)	0.3483 (3)	0.19990 (9)	0.0680 (6)
H3O	−0.036 (2)	0.286 (6)	0.2288 (19)	0.102*
C10	0.11973 (15)	0.5289 (3)	0.09459 (12)	0.0600 (7)
H10A	0.1681	0.5203	0.0729	0.072*
H10B	0.0899	0.6163	0.0689	0.072*
C11	0.12997 (17)	0.6026 (5)	0.16224 (16)	0.0775 (9)
H11A	0.1668	0.5252	0.1844	0.093*
H11B	0.1518	0.7254	0.1576	0.093*
O4	0.07285 (19)	0.6183 (4)	0.20375 (14)	0.1263 (13)
H4O	0.049 (3)	0.532 (10)	0.207 (3)	0.190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0538 (10)	0.1121 (17)	0.0539 (10)	0.0251 (9)	−0.0090 (8)	−0.0026 (10)
O2	0.0809 (11)	0.0353 (8)	0.0632 (10)	0.0006 (7)	0.0116 (8)	0.0062 (7)
S1	0.0454 (3)	0.0439 (3)	0.0411 (3)	0.00854 (19)	0.0022 (2)	−0.0011 (2)
C1	0.0384 (9)	0.0358 (9)	0.0404 (10)	0.0034 (7)	0.0051 (8)	−0.0069 (8)
C2	0.0441 (11)	0.0514 (12)	0.0548 (13)	−0.0088 (9)	0.0050 (9)	−0.0136 (10)
C3	0.0587 (13)	0.0475 (12)	0.0664 (15)	−0.0128 (10)	0.0219 (11)	−0.0084 (11)
C4	0.0680 (14)	0.0399 (11)	0.0508 (12)	0.0061 (9)	0.0193 (11)	−0.0007 (9)
C7	0.116 (3)	0.080 (2)	0.0577 (16)	0.0089 (18)	0.0318 (16)	0.0138 (15)
C5	0.0536 (12)	0.0520 (12)	0.0447 (11)	0.0054 (10)	−0.0009 (9)	−0.0071 (10)
C6	0.0383 (10)	0.0427 (11)	0.0449 (11)	−0.0004 (8)	0.0026 (8)	−0.0057 (8)
N1	0.0449 (9)	0.0390 (9)	0.0447 (9)	−0.0018 (6)	0.0129 (7)	−0.0056 (7)
C8	0.0488 (11)	0.0580 (13)	0.0418 (11)	0.0102 (9)	0.0038 (9)	−0.0003 (10)
C9	0.0537 (13)	0.0734 (16)	0.0634 (15)	−0.0154 (12)	0.0206 (11)	−0.0090 (13)
O3	0.0879 (13)	0.0678 (12)	0.0484 (10)	−0.0134 (9)	0.0284 (9)	0.0010 (8)
C10	0.0765 (15)	0.0487 (13)	0.0548 (14)	−0.0185 (11)	0.0248 (12)	−0.0147 (11)
C11	0.0856 (19)	0.080 (2)	0.0669 (18)	−0.0254 (15)	0.0062 (14)	−0.0239 (15)
O4	0.171 (3)	0.116 (2)	0.0927 (17)	−0.0743 (19)	0.0787 (18)	−0.0682 (16)

Geometric parameters (Å, º) top

O1—S1	1.4220 (18)	C6—H6	0.9300
O2—S1	1.4291 (18)	N1—C8	1.465 (3)
S1—N1	1.6252 (17)	N1—C10	1.477 (3)
S1—C1	1.761 (2)	C8—C9	1.503 (3)
C1—C2	1.388 (3)	C8—H8A	0.9700
C1—C6	1.385 (3)	C8—H8B	0.9700
C2—C3	1.375 (4)	C9—O3	1.413 (3)
C2—H2	0.9300	C9—H9A	0.9700
C3—C4	1.392 (4)	C9—H9B	0.9700
C3—H3	0.9300	O3—H3O	0.75 (4)
C4—C5	1.385 (3)	C10—C11	1.454 (4)
C4—C7	1.504 (3)	C10—H10A	0.9700
C7—H7A	0.9600	C10—H10B	0.9700
C7—H7B	0.9600	C11—O4	1.319 (4)
C7—H7C	0.9600	C11—H11A	0.9700
C5—C6	1.382 (3)	C11—H11B	0.9700
C5—H5	0.9300	O4—H4O	0.76 (7)

O1—S1—O2	120.20 (12)	C8—N1—S1	117.52 (14)
O1—S1—N1	107.31 (11)	C10—N1—S1	116.78 (14)
O2—S1—N1	106.67 (10)	N1—C8—C9	112.75 (19)
O1—S1—C1	107.29 (10)	N1—C8—H8A	109.0
O2—S1—C1	107.90 (10)	C9—C8—H8A	109.0
N1—S1—C1	106.77 (9)	N1—C8—H8B	109.0
C2—C1—C6	120.13 (19)	C9—C8—H8B	109.0
C2—C1—S1	120.15 (17)	H8A—C8—H8B	107.8
C6—C1—S1	119.70 (15)	O3—C9—C8	109.9 (2)
C3—C2—C1	119.6 (2)	O3—C9—H9A	109.7
C3—C2—H2	120.2	C8—C9—H9A	109.7
C1—C2—H2	120.2	O3—C9—H9B	109.7
C2—C3—C4	121.3 (2)	C8—C9—H9B	109.7
C2—C3—H3	119.3	H9A—C9—H9B	108.2
C4—C3—H3	119.3	C9—O3—H3O	107 (3)
C5—C4—C3	118.0 (2)	C11—C10—N1	114.8 (2)
C5—C4—C7	120.6 (3)	C11—C10—H10A	108.6
C3—C4—C7	121.3 (2)	N1—C10—H10A	108.6
C4—C7—H7A	109.5	C11—C10—H10B	108.6
C4—C7—H7B	109.5	N1—C10—H10B	108.6
H7A—C7—H7B	109.5	H10A—C10—H10B	107.6
C4—C7—H7C	109.5	O4—C11—C10	120.6 (3)
H7A—C7—H7C	109.5	O4—C11—H11A	107.2
H7B—C7—H7C	109.5	C10—C11—H11A	107.2
C6—C5—C4	121.5 (2)	O4—C11—H11B	107.2
C6—C5—H5	119.2	C10—C11—H11B	107.2
C4—C5—H5	119.2	H11A—C11—H11B	106.8
C5—C6—C1	119.36 (19)	C10—C11—H4O	105 (2)
C5—C6—H6	120.3	H11A—C11—H4O	99.7
C1—C6—H6	120.3	H11B—C11—H4O	129.5
C8—N1—C10	117.96 (18)	C11—O4—H4O	115 (5)

O1—S1—C1—C2	−22.1 (2)	C2—C1—C6—C5	−0.7 (3)
O2—S1—C1—C2	−152.92 (17)	S1—C1—C6—C5	177.53 (16)
N1—S1—C1—C2	92.73 (18)	O1—S1—N1—C8	−159.22 (16)
O1—S1—C1—C6	159.73 (17)	O2—S1—N1—C8	−29.17 (18)
O2—S1—C1—C6	28.87 (19)	C1—S1—N1—C8	86.00 (16)
N1—S1—C1—C6	−85.47 (17)	O1—S1—N1—C10	52.0 (2)
C6—C1—C2—C3	1.2 (3)	O2—S1—N1—C10	−177.94 (17)
S1—C1—C2—C3	−177.04 (17)	C1—S1—N1—C10	−62.76 (19)
C1—C2—C3—C4	−0.4 (3)	C10—N1—C8—C9	−119.1 (2)
C2—C3—C4—C5	−0.9 (3)	S1—N1—C8—C9	92.5 (2)
C2—C3—C4—C7	179.5 (2)	N1—C8—C9—O3	63.5 (3)
C3—C4—C5—C6	1.4 (3)	C8—N1—C10—C11	94.0 (3)
C7—C4—C5—C6	−179.0 (2)	S1—N1—C10—C11	−117.4 (2)
C4—C5—C6—C1	−0.6 (3)	N1—C10—C11—O4	−54.6 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3—H3O···O4ⁱ	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10—H10A···O1ⁱⁱ	0.97	2.61	3.361 (3)	135
C3—H3···Cg1ⁱⁱⁱ	0.93	2.78	3.522 (2)	138

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

Experimental details

Crystal data
Chemical formula	C₁₁H₁₇NO₄S
M_r	259.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	17.9308 (5), 7.1881 (2), 19.8333 (6)
V (Å³)	2556.28 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.16 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3124, 3124, 2343
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.161, 0.99
No. of reflections	3124
No. of parameters	161
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.39

Computer programs: APEX2 (Bruker, 2007), APEX2 and SAINT (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004), PLATON (Spek, 2009) and publCIF (Westrip 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O3	0.76 (7)	1.89 (7)	2.634 (3)	166 (7)
O3—H3O···O4ⁱ	0.75 (4)	1.92 (4)	2.661 (3)	172 (4)
C10—H10A···O1ⁱⁱ	0.97	2.61	3.361 (3)	134.5
C3—H3···Cg1ⁱⁱⁱ	0.93	2.78	3.522 (2)	138

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

Acknowledgements

The authors acknowledge Mr Ejaz for his kind assistance with the X-ray data collection.

References

Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338. Web of Science CrossRef CAS IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casini, A., Scozzafava, A., Mastrolorenzo, A. & Supuran, L. T. (2002). Curr. Cancer Drug Targets, 2, 55–75. Web of Science CrossRef PubMed CAS Google Scholar
Chambers, H. F. & Jawetz, E. (1998). Sulfonamides, trimethoprim, and quinolones, in basic and clinical pharmacology, edited by B. G. Katzung, pp. 761–763. Stamford: Appleton–Lange. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hori, Y., Pei, N., Kumagai, R. & Sasanuma, Y. (2011). Polym. Chem. 2, 2183–2185. Web of Science CrossRef CAS 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
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
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yoon, I., Park, K.-M. & Lee, S. S. (2001). Acta Cryst. C57, 321–322. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3142

doi:10.1107/S1600536812041682

Open

access