N-Butyl-4-hydr­oxy-2-methyl-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide

Ahmad, M.; Siddiqui, H.L.; Ahmad, S.; Farooq, S.U.; Parvez, M.

doi:10.1107/S160053680801670X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 7| July 2008| Pages o1213-o1214

doi:10.1107/S160053680801670X

Open

access

N-Butyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Matloob Ahmad,^a Hamid Latif Siddiqui,^a ^* Saeed Ahmad,^b Syed Umar Farooq ^a and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bDepartment of Chemistry, University of Science and Technology, Bannu, Pakistan, and ^cDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: drhamidlatif@yahoo.com

(Received 10 May 2008; accepted 1 June 2008; online 7 June 2008)

The title compound, C₁₄H₁₈N₂O₄S, contains hydrogen-bonded dimeric pairs of molecules arranged around inversion centers, forming 14-membered rings with an R₂²(14) motif. The structure is stabilized by extensive intramolecular interactions. The thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by −0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008 ); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008 ); Bernstein et al. (1994 ); Gupta et al. (1993 , 2002 ); Kojić-Prodić & Rużić-Toroš (1982 ); Lombardino (1971 ); Lombardino & Wiseman (1972 ); Rehman et al. (2005 , 2006 ); Sianesi et al. (1973 ); Siddiqui et al. (2008 ); Zinnes et al. (1982 ); Drebushchak et al. (2006 ).

Experimental

Crystal data

C₁₄H₁₈N₂O₄S
M_r = 310.36
Monoclinic, P 2₁ /c
a = 10.233 (2) Å
b = 14.780 (4) Å
c = 10.365 (5) Å
β = 108.79 (2)°
V = 1484.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 173 (2) K
0.14 × 0.12 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.968, T_max = 0.986
12380 measured reflections
3405 independent reflections
2646 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.100
S = 1.03
3405 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N⋯O2ⁱ	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N⋯N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B⋯O2	0.98	2.49	2.864 (2)	102
Symmetry code: (i) -x+1, -y, -z+2.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: HKL DENZO (Otwinowski & Minor, 1997 ); data reduction: 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, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks Global, I. DOI: 10.1107/S160053680801670X/bh2176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680801670X/bh2176Isup2.hkl

checkCIF report

Comment top

Several benzothiazine derivatives like piroxicam, sudoxicam (Lombardino & Wiseman, 1972; Rehman et al., 2005) and isoxicam (Zinnes et al., 1982) have been reported in the literature to be potential anti-inflammatory agents. Some of the derivatives of benzothiazines are found to be analgesic (Gupta et al., 2002), anti-cancer (Gupta et al., 1993) and exhibitors of central nervous system activity (Sianesi et al., 1973). We have reported anti-bacterial activities (Rehman et al., 2006) of a series of 1,2-benzothiazines. In continuation of our work on 1,2-benzothiazines 1,1-dioxides (Ahmad, Siddiqui, Ahmad, Irfan Ashiq & Tizzard, 2008; Ahmad, Siddiqui, Zia-ur-Rehman, Ashiq & Tizzard, 2008), we report in this paper the crystal structure of the title compound, (I), which was patented for Pfizer Inc. (Lombardino, 1971).

The structure of (I), (Fig. 1), contains dimeric pairs of molecules lying about inversion centers resulting from N2—H2N···O2 hydrogen bonds (Fig. 2). The 14-membered rings thus formed represent R₂²(14) motif in the graph set notation (Bernstein et al., 1994). Similar hydrogen-bonded dimers have been reported in structures related to the title compound (Siddiqui et al., 2008; Drebushchak et al., 2006; Kojić-Prodić & Rużić-Toroš, 1982). The structure is stabilized by extensive intramolecular interactions (Fig. 1 and Table 1). The thiazine ring in (I) adopts a half-chair conformation with atoms S1 and N1 displaced by -0.485 (3) and 0.296 (3) Å, respectively, from the plane formed by the remaining atoms of the ring.

Related literature top

For related literature, see: Ahmad, Siddiqui, Ahmad et al. (2008); Ahmad, Siddiqui, Zia-ur-Rehman et al. (2008); Bernstein et al. (1994); Gupta et al. (1993, 2002); Kojić-Prodić & Rużić-Toroš (1982); Lombardino (1971); Lombardino & Wiseman (1972); Rehman et al. (2005, 2006); Sianesi et al. (1973); Siddiqui et al. (2008); Zinnes et al. (1982); Drebushchak et al. (2006).

Experimental top

Methyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (1.0 g, 3.72 mmoles) was dissolved in n-butyl amine (5 ml) in a test tube. The mixture was placed at room temperature for 7 days. Crystals of (I) suitable for crystallographic analysis were found, which were washed with MeOH.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP-3 (Farrugia, 1997) drawing of (I) with displacement ellipsoids plotted at 50% probability level; intramolecular interactions have been indicated by dashed lines.
	Fig. 2. Unit cell packing of (I) showing hydrogen bonds with dashed lines; H atoms not involved in hydrogen bonds have been omitted.

N-Butyl-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide top

Crystal data top

C₁₄H₁₈N₂O₄S	F(000) = 656
M_r = 310.36	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12380 reflections
a = 10.233 (2) Å	θ = 3.4–27.6°
b = 14.780 (4) Å	µ = 0.24 mm⁻¹
c = 10.365 (5) Å	T = 173 K
β = 108.79 (2)°	Prism, colorless
V = 1484.1 (9) Å³	0.14 × 0.12 × 0.06 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	2646 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ω and ϕ scans	θ_max = 27.6°, θ_min = 3.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −13→13
T_min = 0.968, T_max = 0.986	k = −19→19
12380 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.045P)² + 0.606P] where P = (F_o² + 2F_c²)/3
3405 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₄H₁₈N₂O₄S	V = 1484.1 (9) Å³
M_r = 310.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.233 (2) Å	µ = 0.24 mm⁻¹
b = 14.780 (4) Å	T = 173 K
c = 10.365 (5) Å	0.14 × 0.12 × 0.06 mm
β = 108.79 (2)°

Data collection top

Nonius KappaCCD diffractometer	3405 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2646 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.986	R_int = 0.041
12380 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.100	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
3405 reflections	Δρ_min = −0.43 e Å⁻³
198 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.53051 (4)	0.13868 (3)	0.96872 (5)	0.03033 (13)
O1	0.45310 (12)	0.12905 (9)	0.82760 (14)	0.0384 (3)
O2	0.46724 (13)	0.11547 (9)	1.06916 (15)	0.0400 (3)
O3	0.86081 (13)	0.22923 (9)	0.83438 (13)	0.0336 (3)
H3O	0.899 (2)	0.1799 (16)	0.816 (2)	0.050*
O4	0.92527 (12)	0.06200 (9)	0.82242 (13)	0.0356 (3)
N1	0.67274 (13)	0.07980 (9)	0.99855 (14)	0.0265 (3)
N2	0.78434 (15)	−0.04424 (10)	0.86553 (16)	0.0327 (3)
H2N	0.714 (2)	−0.0525 (14)	0.894 (2)	0.039*
C1	0.59359 (17)	0.24980 (11)	0.99677 (17)	0.0283 (4)
C2	0.53309 (18)	0.31325 (12)	1.05849 (19)	0.0342 (4)
H2	0.4587	0.2967	1.0897	0.041*
C3	0.58309 (19)	0.40116 (12)	1.07376 (19)	0.0359 (4)
H3	0.5430	0.4455	1.1159	0.043*
C4	0.69144 (19)	0.42436 (12)	1.02763 (18)	0.0349 (4)
H4	0.7235	0.4851	1.0363	0.042*
C5	0.75381 (17)	0.36033 (12)	0.96906 (18)	0.0309 (4)
H5	0.8289	0.3772	0.9392	0.037*
C6	0.70664 (17)	0.27103 (11)	0.95385 (17)	0.0276 (4)
C7	0.77716 (16)	0.19970 (12)	0.90287 (17)	0.0272 (4)
C8	0.76003 (16)	0.11021 (12)	0.92283 (17)	0.0269 (4)
C9	0.74832 (19)	0.05636 (13)	1.14249 (18)	0.0355 (4)
H9A	0.8206	0.0121	1.1457	0.043*
H9B	0.6839	0.0305	1.1848	0.043*
H9C	0.7905	0.1110	1.1921	0.043*
C10	0.82934 (17)	0.04054 (12)	0.86719 (17)	0.0288 (4)
C11	0.8470 (2)	−0.12047 (12)	0.8176 (2)	0.0385 (4)
H11A	0.9478	−0.1107	0.8430	0.046*
H11B	0.8091	−0.1238	0.7170	0.046*
C12	0.82004 (18)	−0.20820 (12)	0.8775 (2)	0.0335 (4)
H12A	0.7192	−0.2189	0.8486	0.040*
H12B	0.8537	−0.2034	0.9781	0.040*
C13	0.88952 (19)	−0.28900 (12)	0.83487 (19)	0.0339 (4)
H13A	0.8496	−0.2975	0.7351	0.041*
H13B	0.9892	−0.2761	0.8562	0.041*
C14	0.8724 (2)	−0.37560 (13)	0.9058 (2)	0.0405 (5)
H14A	0.9237	−0.4245	0.8799	0.049*
H14B	0.7743	−0.3916	0.8787	0.049*
H14C	0.9079	−0.3668	1.0048	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0252 (2)	0.0286 (2)	0.0417 (3)	−0.00243 (16)	0.01704 (18)	−0.00165 (18)
O1	0.0263 (6)	0.0414 (8)	0.0450 (8)	−0.0039 (5)	0.0078 (5)	−0.0038 (6)
O2	0.0400 (7)	0.0340 (7)	0.0597 (9)	−0.0031 (5)	0.0352 (7)	−0.0005 (6)
O3	0.0347 (7)	0.0328 (7)	0.0411 (7)	−0.0041 (5)	0.0232 (6)	0.0015 (6)
O4	0.0316 (6)	0.0379 (7)	0.0455 (8)	−0.0004 (5)	0.0239 (6)	0.0008 (6)
N1	0.0267 (7)	0.0273 (7)	0.0306 (8)	−0.0003 (5)	0.0160 (6)	0.0018 (6)
N2	0.0306 (8)	0.0311 (8)	0.0433 (9)	−0.0001 (6)	0.0215 (7)	−0.0031 (7)
C1	0.0269 (8)	0.0267 (8)	0.0330 (9)	0.0003 (6)	0.0121 (7)	0.0023 (7)
C2	0.0317 (9)	0.0342 (10)	0.0404 (10)	0.0042 (7)	0.0167 (8)	0.0028 (8)
C3	0.0400 (10)	0.0296 (9)	0.0393 (10)	0.0073 (8)	0.0142 (8)	0.0019 (8)
C4	0.0407 (10)	0.0269 (9)	0.0353 (10)	−0.0007 (7)	0.0097 (8)	0.0024 (7)
C5	0.0306 (9)	0.0309 (9)	0.0315 (9)	−0.0027 (7)	0.0104 (7)	0.0040 (7)
C6	0.0255 (8)	0.0307 (9)	0.0267 (8)	−0.0011 (7)	0.0087 (7)	0.0019 (7)
C7	0.0229 (8)	0.0338 (9)	0.0264 (8)	−0.0028 (6)	0.0098 (7)	0.0014 (7)
C8	0.0234 (8)	0.0318 (9)	0.0282 (9)	−0.0018 (6)	0.0122 (7)	0.0008 (7)
C9	0.0385 (10)	0.0390 (10)	0.0331 (10)	−0.0019 (8)	0.0171 (8)	0.0021 (8)
C10	0.0245 (8)	0.0345 (9)	0.0290 (9)	0.0006 (7)	0.0107 (7)	0.0003 (7)
C11	0.0432 (10)	0.0326 (10)	0.0502 (12)	0.0037 (8)	0.0294 (9)	−0.0028 (8)
C12	0.0324 (9)	0.0340 (10)	0.0398 (10)	0.0013 (7)	0.0194 (8)	−0.0026 (8)
C13	0.0329 (9)	0.0348 (10)	0.0367 (10)	0.0015 (7)	0.0152 (8)	−0.0036 (8)
C14	0.0365 (10)	0.0356 (10)	0.0486 (12)	−0.0003 (8)	0.0128 (9)	−0.0003 (9)

Geometric parameters (Å, º) top

S1—O1	1.4286 (15)	C5—C6	1.397 (2)
S1—O2	1.4335 (14)	C5—H5	0.9500
S1—N1	1.6375 (14)	C6—C7	1.469 (2)
S1—C1	1.7543 (18)	C7—C8	1.359 (2)
O3—C7	1.349 (2)	C8—C10	1.470 (2)
O3—H3O	0.88 (2)	C9—H9A	0.9800
O4—C10	1.254 (2)	C9—H9B	0.9800
N1—C8	1.438 (2)	C9—H9C	0.9800
N1—C9	1.484 (2)	C11—C12	1.501 (3)
N2—C10	1.333 (2)	C11—H11A	0.9900
N2—C11	1.460 (2)	C11—H11B	0.9900
N2—H2N	0.87 (2)	C12—C13	1.526 (2)
C1—C2	1.388 (2)	C12—H12A	0.9900
C1—C6	1.402 (2)	C12—H12B	0.9900
C2—C3	1.387 (3)	C13—C14	1.514 (3)
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.385 (3)	C13—H13B	0.9900
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.386 (3)	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800

O1—S1—O2	119.25 (9)	C7—C8—C10	121.34 (15)
O1—S1—N1	107.84 (8)	N1—C8—C10	117.28 (14)
O2—S1—N1	108.51 (8)	N1—C9—H9A	109.5
O1—S1—C1	108.42 (8)	N1—C9—H9B	109.5
O2—S1—C1	109.38 (8)	H9A—C9—H9B	109.5
N1—S1—C1	102.07 (8)	N1—C9—H9C	109.5
C7—O3—H3O	104.4 (15)	H9A—C9—H9C	109.5
C8—N1—C9	114.06 (13)	H9B—C9—H9C	109.5
C8—N1—S1	113.67 (11)	O4—C10—N2	122.76 (16)
C9—N1—S1	117.24 (11)	O4—C10—C8	120.15 (15)
C10—N2—C11	122.83 (15)	N2—C10—C8	117.08 (15)
C10—N2—H2N	116.6 (14)	N2—C11—C12	111.55 (15)
C11—N2—H2N	120.6 (14)	N2—C11—H11A	109.3
C2—C1—C6	122.08 (16)	C12—C11—H11A	109.3
C2—C1—S1	120.92 (13)	N2—C11—H11B	109.3
C6—C1—S1	117.00 (13)	C12—C11—H11B	109.3
C3—C2—C1	118.85 (16)	H11A—C11—H11B	108.0
C3—C2—H2	120.6	C11—C12—C13	113.08 (14)
C1—C2—H2	120.6	C11—C12—H12A	109.0
C4—C3—C2	119.98 (17)	C13—C12—H12A	109.0
C4—C3—H3	120.0	C11—C12—H12B	109.0
C2—C3—H3	120.0	C13—C12—H12B	109.0
C3—C4—C5	121.00 (17)	H12A—C12—H12B	107.8
C3—C4—H4	119.5	C14—C13—C12	112.53 (15)
C5—C4—H4	119.5	C14—C13—H13A	109.1
C4—C5—C6	120.23 (16)	C12—C13—H13A	109.1
C4—C5—H5	119.9	C14—C13—H13B	109.1
C6—C5—H5	119.9	C12—C13—H13B	109.1
C5—C6—C1	117.78 (16)	H13A—C13—H13B	107.8
C5—C6—C7	121.80 (15)	C13—C14—H14A	109.5
C1—C6—C7	120.31 (15)	C13—C14—H14B	109.5
O3—C7—C8	122.01 (15)	H14A—C14—H14B	109.5
O3—C7—C6	115.20 (15)	C13—C14—H14C	109.5
C8—C7—C6	122.79 (15)	H14A—C14—H14C	109.5
C7—C8—N1	121.38 (14)	H14B—C14—H14C	109.5

O1—S1—N1—C8	61.67 (13)	S1—C1—C6—C7	−6.9 (2)
O2—S1—N1—C8	−167.86 (11)	C5—C6—C7—O3	−19.3 (2)
C1—S1—N1—C8	−52.42 (13)	C1—C6—C7—O3	164.56 (15)
O1—S1—N1—C9	−161.75 (12)	C5—C6—C7—C8	160.65 (16)
O2—S1—N1—C9	−31.28 (14)	C1—C6—C7—C8	−15.5 (2)
C1—S1—N1—C9	84.16 (13)	O3—C7—C8—N1	178.67 (14)
O1—S1—C1—C2	103.81 (15)	C6—C7—C8—N1	−1.3 (2)
O2—S1—C1—C2	−27.73 (17)	O3—C7—C8—C10	−1.7 (3)
N1—S1—C1—C2	−142.53 (15)	C6—C7—C8—C10	178.33 (15)
O1—S1—C1—C6	−76.03 (15)	C9—N1—C8—C7	−98.65 (19)
O2—S1—C1—C6	152.43 (13)	S1—N1—C8—C7	39.3 (2)
N1—S1—C1—C6	37.63 (15)	C9—N1—C8—C10	81.71 (18)
C6—C1—C2—C3	2.3 (3)	S1—N1—C8—C10	−140.30 (13)
S1—C1—C2—C3	−177.53 (14)	C11—N2—C10—O4	3.1 (3)
C1—C2—C3—C4	0.1 (3)	C11—N2—C10—C8	−177.77 (16)
C2—C3—C4—C5	−1.7 (3)	C7—C8—C10—O4	13.4 (3)
C3—C4—C5—C6	0.9 (3)	N1—C8—C10—O4	−166.94 (15)
C4—C5—C6—C1	1.4 (2)	C7—C8—C10—N2	−165.76 (16)
C4—C5—C6—C7	−174.82 (16)	N1—C8—C10—N2	13.9 (2)
C2—C1—C6—C5	−3.0 (3)	C10—N2—C11—C12	156.43 (17)
S1—C1—C6—C5	176.82 (13)	N2—C11—C12—C13	−177.35 (16)
C2—C1—C6—C7	173.25 (16)	C11—C12—C13—C14	174.83 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N···O2ⁱ	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N···N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B···O2	0.98	2.49	2.864 (2)	102

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₂O₄S
M_r	310.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	10.233 (2), 14.780 (4), 10.365 (5)
β (°)	108.79 (2)
V (Å³)	1484.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.14 × 0.12 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.968, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	12380, 3405, 2646
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.100, 1.03
No. of reflections	3405
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.43

Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.88 (2)	1.76 (2)	2.572 (2)	153 (2)
N2—H2N···O2ⁱ	0.87 (2)	2.21 (2)	3.052 (2)	161 (2)
N2—H2N···N1	0.87 (2)	2.34 (2)	2.753 (2)	109 (2)
C9—H9B···O2	0.98	2.49	2.864 (2)	102

Symmetry code: (i) −x+1, −y, −z+2.

References

Ahmad, M., Siddiqui, H. L., Ahmad, S., Irfan Ashiq, M. & Tizzard, G. J. (2008). Acta Cryst. E64, o594. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M., Ashiq, M. I. & Tizzard, G. J. (2008). Acta Cryst. E64, o788. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, edited by H.-B. Bürgi & J. D. Dunitz, Vol. 2, pp. 431–507. New York: VCH. Google Scholar
Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
Drebushchak, T. N., Pankrushina, N. N., Shakhtshneider, T. P. & Apenina, S. A. (2006). Acta Cryst. C62, o429–o431. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gupta, S. K., Bansal, P., Bhardwaj, R. K., Jaiswal, J. & Velpandian, T. (2002). Skin Pharmacol. Appl. Skin Physiol. 15, 105–111. Web of Science CrossRef PubMed CAS Google Scholar
Gupta, R. R., Dev, P. K., Sharma, M. L., Rajoria, C. M., Gupta, A. & Nyati, M. (1993). Anticancer Drugs, 4, 589–592. CrossRef CAS PubMed Web of Science Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Kojić-Prodić, B. & Rużić-Toroš, Ž. (1982). Acta Cryst. B38, 2948–2951. CSD CrossRef Web of Science IUCr Journals Google Scholar
Lombardino, J. G. (1971). US Patent No. 3 591 584. Google Scholar
Lombardino, J. G. & Wiseman, E. H. (1972). J. Med. Chem. 15, 848–849. CrossRef CAS PubMed Web of Science 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
Rehman, M. Z., Choudary, J. A. & Ahmad, S. (2005). Bull. Korean Chem. Soc. 54, 1171–1175. Google Scholar
Rehman, M. Z., Choudary, J. A., Ahmad, S. & Siddiqui, H. L. (2006). Chem. Pharm. Bull. 54, 1175–1178. Web of Science CrossRef PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sianesi, E., Redaelli, R., Magistretti, M. J. & Massarani, E. (1973). J. Med. Chem. 16, 1133–1137. CrossRef CAS PubMed Web of Science Google Scholar
Siddiqui, W. A., Ahmad, S., Tariq, M. I., Siddiqui, H. L. & Parvez, M. (2008). Acta Cryst. C64, o4–o6. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zinnes, H., Sircar, J. C., Lindo, N., Schwartz, M. L., Fabian, A. C., Shavel, J. Jr, Kasulanis, C. F., Genzer, J. D., Lutomski, C. & DiPasquale, G. (1982). J. Med. Chem. 25, 12–18. CrossRef CAS PubMed Web of Science 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 64| Part 7| July 2008| Pages o1213-o1214

doi:10.1107/S160053680801670X

Open

access