N-[2-(Amino­carbon­yl)phen­yl]-4-hydr­oxy-2-methyl-2H-1,2-benzothia­zine-3-carboxamide 1,1-dioxide

Arshad, M.N.; Zia-ur-Rehman, M.; Khan, I.U.

doi:10.1107/S1600536809038951

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2596

doi:10.1107/S1600536809038951

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N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Muhammad Nadeem Arshad,^a Muhammad Zia-ur-Rehman ^b ^* and Islam Ullah Khan ^a

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, and ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Ferozpure Road, Lahore 54600, Pakistan
^*Correspondence e-mail: rehman_pcsir@hotmail.com

(Received 24 September 2009; accepted 25 September 2009; online 30 September 2009)

In the title compound, C₁₇H₁₅N₃O₅S, the thiazine ring adopts a distorted half-chair conformation. The molecular structure is stabilized by intramolecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonding. Pairs of molecules are bound together as centrosymmetric dimers through N—H⋯O hydrogen bonds.

Related literature

For the synthesis of related molecules, see: Braun (1923 ); Ahmad et al. (2008 ); Zia-ur-Rehman et al. (2005 , 2009 ). For the biological activity of 1,2-benzothiazine 1,1-dioxides, see: Bihovsky et al. (2004 ); Turck et al. (1996 ); Zia-ur-Rehman et al. (2006 ). For similar molecules, see: Kojić-Prodić & Rużić-Toroš (1982 ); Siddiqui et al. (2009 ); Weast et al. (1984 ); Zia-ur-Rehman et al. (2007 ).

Experimental

Crystal data

C₁₇H₁₅N₃O₅S
M_r = 373.38
Monoclinic, P 2₁ /c
a = 8.1377 (6) Å
b = 7.0515 (6) Å
c = 29.069 (2) Å
β = 96.502 (3)°
V = 1657.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.39 × 0.25 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.915, T_max = 0.975
16109 measured reflections
3753 independent reflections
3011 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.213
S = 1.09
3753 reflections
237 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.82	1.85	2.569 (5)	145
N2—H2⋯O5	0.86	1.92	2.607 (5)	136
N2—H2⋯N1	0.86	2.28	2.728 (5)	113
N3—H3A⋯O5ⁱ	0.86	2.22	2.941 (6)	141
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: 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: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038951/bt5073sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038951/bt5073Isup2.hkl

checkCIF report

Comment top

Owing to the verstaile applications of 1,2-benzothiazine 1,1-dioxides, considerable attention has been given to their synthesis since their very first synthesis (Braun, 1923). Among these, Piroxicam (Zia-ur-Rehman et al., 2005), and Meloxicam (Turck et al., 1996) are familiar for their analgesic action and are being used world wide as non-steroidal anti-inflammatory drugs (NSAIDs). Some of the 3,4-dihydro-1,2-benzothiazine-3-carboxylate 1,1-dioxide α-ketomide and P(2)—P(3) peptide mimetic aldehyde compounds act as potent calpain I inhibitors (Bihovsky et al., 2004) while 1,2-benzothiazin-3-yl-quinazolin-4(3H)-ones possess anti-bacterial properties (Zia-ur-Rehman et al., 2006).

In continuation of our work on the synthesis (Zia-ur-Rehman et al., 2006, biological activity (Zia-ur-Rehman et al., 2009) and crystal structures (Zia-ur-Rehman et al., 2007; Ahmad et al., 2008, Siddiqui et al., 2009) of various 1,2-benzothiazine-1,1-dioxides, we herein report the crystal structure of the title compound (I) (Scheme and figure 1). Like its already reported dimethylsulfoxide solvate analogue (Zia-ur-Rehman et al., 2007), thiazine ring involving two double bonds, exhibits sofa conformation; with S1/C1/C2/C7 relatively planar and N1 showing significant departure from plane due to its pyramidal geometry. The enolic hydrogen on O1 is involved in intramolecular hydrogen bonding [O1—H1···O4] with the carbonyl oxygen at C9 giving rise to a six-membered hydrogen bond ring (Table 1). Atom H2 forms hydrogen bonds with both N1 and O5 giving rise to five and six-membered hydrogen bond rings respectively. The C1—S1 [1.755 Å] bond is shorter than a normal C—S single bond (1.81–2.55 Å) (Weast et al., 1984) due to partial double bond character and is in agreement with similar molecules (Kojić-Prodić & Rużić-Toroš, 1982). Each molecule is centrosymmetrically linked to its adjacent one forming a dimer through intermolecular [N—H3B···O5] hydrogen bonds (Fig. 2).

Related literature top

For synthesis of related molecules, see: Braun (1923); Ahmad et al. (2008); Zia-ur-Rehman et al. (2005); Zia-ur-Rehman et al. (2009). For biological activity of 1,2-benzothiazine 1,1-dioxides, see: Bihovsky et al. (2004); Turck et al. (1996); Zia-ur-Rehman et al. (2006). For similar molecules, see: Kojić-Prodić & Rużić-Toroš (1982); Siddiqui et al. (2009); Weast et al. (1984); Zia-ur-Rehman et al. (2007).

Experimental top

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine- 3-carboxamide 1,1-dioxide was synthesized according to a literature method (Zia-ur-Rehman et al., 2006). Suitable crystals were obtained by dissoving the compound in chloroform followed by slow evaporation at room temperature.The compound was dissolved in a mixture of methanol and DMSO (80:20 v/v) at room temperature. Crystals were obtained by slow evaporation and dried under high vacuum.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids at the 50% probability level.
	Fig. 2. Perspective view of the three-dimensional crystal packing showing hydrogen-bonded interactions (dashed lines). H atoms not involved in hydrogen bonding have been omitted for clarity.

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2- benzothiazine-3-carboxamide 1,1-dioxide top

Crystal data top

C₁₇H₁₅N₃O₅S	F(000) = 776
M_r = 373.38	D_x = 1.496 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6164 reflections
a = 8.1377 (6) Å	θ = 2.5–27.1°
b = 7.0515 (6) Å	µ = 0.23 mm⁻¹
c = 29.069 (2) Å	T = 296 K
β = 96.502 (3)°	Needles, colourless
V = 1657.3 (2) Å³	0.39 × 0.25 × 0.11 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3753 independent reflections
Radiation source: fine-focus sealed tube	3011 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −10→10
T_min = 0.915, T_max = 0.975	k = −9→9
16109 measured reflections	l = −32→37

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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.213	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0335P)² + 9.427P] where P = (F_o² + 2F_c²)/3
3753 reflections	(Δ/σ)_max < 0.001
237 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₁₇H₁₅N₃O₅S	V = 1657.3 (2) Å³
M_r = 373.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1377 (6) Å	µ = 0.23 mm⁻¹
b = 7.0515 (6) Å	T = 296 K
c = 29.069 (2) Å	0.39 × 0.25 × 0.11 mm
β = 96.502 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3753 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	3011 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.975	R_int = 0.039
16109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	0 restraints
wR(F²) = 0.213	H-atom parameters constrained
S = 1.09	Δρ_max = 0.38 e Å⁻³
3753 reflections	Δρ_min = −0.40 e Å⁻³
237 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
S1	0.35684 (14)	0.5031 (2)	0.33289 (4)	0.0343 (3)
O2	0.2977 (5)	0.6850 (5)	0.34450 (12)	0.0427 (9)
O3	0.5306 (4)	0.4668 (7)	0.33922 (13)	0.0538 (11)
O4	−0.1641 (4)	0.3152 (6)	0.38428 (12)	0.0480 (10)
O5	0.3670 (4)	0.3198 (6)	0.47838 (12)	0.0484 (10)
N1	0.2640 (5)	0.3427 (6)	0.36214 (13)	0.0310 (9)
N2	0.0743 (5)	0.2848 (6)	0.43247 (12)	0.0306 (8)
H2	0.1801	0.2826	0.4328	0.037*
N3	0.3804 (6)	0.4241 (8)	0.55160 (15)	0.0534 (13)
H3A	0.4817	0.4585	0.5513	0.064*
H3B	0.3319	0.4407	0.5761	0.064*
O1	−0.1513 (4)	0.3895 (6)	0.29823 (12)	0.0436 (9)
H1	−0.1968	0.3747	0.3218	0.065*
C1	0.2765 (6)	0.4493 (7)	0.27578 (16)	0.0329 (10)
C2	0.1069 (6)	0.4046 (7)	0.26901 (16)	0.0322 (10)
C3	0.0347 (8)	0.3766 (8)	0.22406 (17)	0.0445 (13)
H3	−0.0780	0.3516	0.2183	0.053*
C4	0.1301 (9)	0.3861 (9)	0.18781 (19)	0.0577 (17)
H4	0.0805	0.3685	0.1577	0.069*
C5	0.2966 (9)	0.4210 (10)	0.19540 (19)	0.0580 (17)
H5	0.3594	0.4221	0.1706	0.070*
C6	0.3718 (7)	0.4546 (9)	0.23979 (19)	0.0470 (14)
H6	0.4845	0.4802	0.2451	0.056*
C7	0.0124 (6)	0.3801 (7)	0.30885 (16)	0.0314 (10)
C8	0.0874 (6)	0.3479 (7)	0.35254 (16)	0.0308 (10)
C9	−0.0106 (6)	0.3133 (7)	0.39093 (15)	0.0315 (10)
C10	0.0150 (6)	0.2579 (6)	0.47583 (15)	0.0287 (9)
C11	0.1236 (6)	0.2888 (7)	0.51660 (16)	0.0323 (10)
C12	0.0636 (7)	0.2643 (7)	0.55876 (17)	0.0402 (12)
H12	0.1350	0.2810	0.5858	0.048*
C13	−0.0980 (7)	0.2160 (8)	0.56205 (18)	0.0441 (13)
H13	−0.1358	0.2046	0.5909	0.053*
C14	−0.2039 (7)	0.1845 (8)	0.5223 (2)	0.0448 (13)
H14	−0.3134	0.1514	0.5245	0.054*
C15	−0.1485 (6)	0.2019 (7)	0.47945 (17)	0.0374 (11)
H15	−0.2197	0.1764	0.4528	0.045*
C16	0.2986 (6)	0.3449 (8)	0.51412 (16)	0.0368 (11)
C17	0.3393 (7)	0.1508 (9)	0.3632 (2)	0.0521 (15)
H17A	0.3025	0.0790	0.3882	0.078*
H17B	0.4576	0.1619	0.3678	0.078*
H17C	0.3065	0.0873	0.3344	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0273 (5)	0.0450 (7)	0.0309 (6)	−0.0003 (5)	0.0047 (4)	0.0006 (5)
O2	0.048 (2)	0.041 (2)	0.0391 (19)	−0.0070 (17)	0.0065 (16)	−0.0037 (16)
O3	0.0284 (18)	0.084 (3)	0.049 (2)	0.000 (2)	0.0067 (16)	0.010 (2)
O4	0.0289 (18)	0.079 (3)	0.0368 (19)	0.0027 (19)	0.0076 (14)	0.0050 (19)
O5	0.0350 (19)	0.075 (3)	0.0354 (19)	−0.0012 (19)	0.0067 (15)	−0.0072 (19)
N1	0.0278 (19)	0.038 (2)	0.0276 (19)	0.0065 (17)	0.0039 (15)	0.0006 (16)
N2	0.0260 (19)	0.039 (2)	0.0280 (19)	0.0001 (17)	0.0063 (15)	0.0053 (17)
N3	0.042 (3)	0.082 (4)	0.036 (2)	−0.006 (3)	0.0011 (19)	−0.009 (2)
O1	0.0307 (18)	0.065 (3)	0.0335 (18)	−0.0013 (18)	−0.0011 (14)	0.0024 (18)
C1	0.040 (3)	0.032 (2)	0.028 (2)	0.001 (2)	0.0079 (19)	0.0016 (18)
C2	0.037 (2)	0.031 (2)	0.029 (2)	−0.001 (2)	0.0064 (19)	0.0005 (19)
C3	0.063 (4)	0.042 (3)	0.029 (2)	−0.005 (3)	0.005 (2)	−0.002 (2)
C4	0.087 (5)	0.056 (4)	0.029 (3)	−0.013 (3)	0.004 (3)	−0.005 (3)
C5	0.076 (4)	0.071 (4)	0.031 (3)	−0.005 (4)	0.024 (3)	−0.004 (3)
C6	0.046 (3)	0.057 (4)	0.041 (3)	−0.003 (3)	0.016 (2)	−0.001 (3)
C7	0.030 (2)	0.034 (2)	0.030 (2)	0.0008 (19)	0.0067 (18)	−0.0015 (19)
C8	0.028 (2)	0.034 (2)	0.030 (2)	0.0032 (19)	0.0029 (17)	0.0000 (19)
C9	0.034 (2)	0.032 (2)	0.029 (2)	0.0000 (19)	0.0034 (18)	−0.0003 (19)
C10	0.032 (2)	0.026 (2)	0.028 (2)	0.0039 (18)	0.0082 (18)	0.0025 (18)
C11	0.039 (3)	0.028 (2)	0.031 (2)	0.004 (2)	0.0072 (19)	0.0029 (19)
C12	0.058 (3)	0.035 (3)	0.029 (2)	0.002 (2)	0.011 (2)	0.001 (2)
C13	0.063 (4)	0.039 (3)	0.035 (3)	0.000 (3)	0.023 (2)	0.003 (2)
C14	0.045 (3)	0.039 (3)	0.054 (3)	−0.002 (2)	0.021 (3)	0.005 (3)
C15	0.036 (3)	0.039 (3)	0.039 (3)	0.000 (2)	0.012 (2)	0.007 (2)
C16	0.034 (3)	0.044 (3)	0.031 (2)	0.006 (2)	−0.0011 (19)	0.003 (2)
C17	0.052 (3)	0.049 (3)	0.058 (4)	0.020 (3)	0.020 (3)	0.014 (3)

Geometric parameters (Å, º) top

S1—O2	1.424 (4)	C4—C5	1.371 (9)
S1—O3	1.428 (4)	C4—H4	0.9300
S1—N1	1.648 (4)	C5—C6	1.384 (8)
S1—C1	1.755 (5)	C5—H5	0.9300
O4—C9	1.242 (6)	C6—H6	0.9300
O5—C16	1.246 (6)	C7—C8	1.364 (6)
N1—C8	1.433 (6)	C8—C9	1.464 (6)
N1—C17	1.484 (7)	C10—C15	1.403 (6)
N2—C9	1.337 (6)	C10—C11	1.413 (6)
N2—C10	1.412 (5)	C11—C12	1.380 (6)
N2—H2	0.8600	C11—C16	1.488 (7)
N3—C16	1.333 (6)	C12—C13	1.372 (8)
N3—H3A	0.8600	C12—H12	0.9300
N3—H3B	0.8600	C13—C14	1.378 (8)
O1—C7	1.335 (5)	C13—H13	0.9300
O1—H1	0.8200	C14—C15	1.379 (7)
C1—C6	1.372 (7)	C14—H14	0.9300
C1—C2	1.407 (7)	C15—H15	0.9300
C2—C3	1.385 (7)	C17—H17A	0.9600
C2—C7	1.471 (6)	C17—H17B	0.9600
C3—C4	1.379 (8)	C17—H17C	0.9600
C3—H3	0.9300

O2—S1—O3	119.2 (3)	O1—C7—C2	114.2 (4)
O2—S1—N1	108.0 (2)	C8—C7—C2	122.3 (4)
O3—S1—N1	108.4 (2)	C7—C8—N1	121.2 (4)
O2—S1—C1	108.6 (2)	C7—C8—C9	120.8 (4)
O3—S1—C1	109.9 (2)	N1—C8—C9	117.9 (4)
N1—S1—C1	101.3 (2)	O4—C9—N2	123.4 (4)
C8—N1—C17	115.4 (4)	O4—C9—C8	120.3 (4)
C8—N1—S1	113.0 (3)	N2—C9—C8	116.3 (4)
C17—N1—S1	115.1 (3)	C15—C10—N2	121.8 (4)
C9—N2—C10	129.2 (4)	C15—C10—C11	119.3 (4)
C9—N2—H2	115.4	N2—C10—C11	118.9 (4)
C10—N2—H2	115.4	C12—C11—C10	118.4 (5)
C16—N3—H3A	120.0	C12—C11—C16	120.9 (5)
C16—N3—H3B	120.0	C10—C11—C16	120.8 (4)
H3A—N3—H3B	120.0	C13—C12—C11	122.1 (5)
C7—O1—H1	109.5	C13—C12—H12	119.0
C6—C1—C2	122.0 (5)	C11—C12—H12	119.0
C6—C1—S1	122.2 (4)	C12—C13—C14	119.7 (5)
C2—C1—S1	115.8 (3)	C12—C13—H13	120.2
C3—C2—C1	118.0 (5)	C14—C13—H13	120.2
C3—C2—C7	121.5 (5)	C13—C14—C15	120.4 (5)
C1—C2—C7	120.5 (4)	C13—C14—H14	119.8
C4—C3—C2	119.9 (6)	C15—C14—H14	119.8
C4—C3—H3	120.1	C14—C15—C10	120.2 (5)
C2—C3—H3	120.1	C14—C15—H15	119.9
C5—C4—C3	121.2 (5)	C10—C15—H15	119.9
C5—C4—H4	119.4	O5—C16—N3	120.8 (5)
C3—C4—H4	119.4	O5—C16—C11	121.6 (4)
C4—C5—C6	120.4 (5)	N3—C16—C11	117.6 (4)
C4—C5—H5	119.8	N1—C17—H17A	109.5
C6—C5—H5	119.8	N1—C17—H17B	109.5
C1—C6—C5	118.5 (5)	H17A—C17—H17B	109.5
C1—C6—H6	120.7	N1—C17—H17C	109.5
C5—C6—H6	120.7	H17A—C17—H17C	109.5
O1—C7—C8	123.6 (4)	H17B—C17—H17C	109.5

O2—S1—N1—C8	58.6 (4)	O1—C7—C8—C9	2.6 (8)
O3—S1—N1—C8	−171.0 (3)	C2—C7—C8—C9	−176.4 (4)
C1—S1—N1—C8	−55.4 (4)	C17—N1—C8—C7	−96.6 (6)
O2—S1—N1—C17	−165.8 (4)	S1—N1—C8—C7	38.8 (6)
O3—S1—N1—C17	−35.4 (4)	C17—N1—C8—C9	82.0 (5)
C1—S1—N1—C17	80.2 (4)	S1—N1—C8—C9	−142.6 (4)
O2—S1—C1—C6	106.1 (5)	C10—N2—C9—O4	−2.0 (8)
O3—S1—C1—C6	−25.9 (5)	C10—N2—C9—C8	176.5 (4)
N1—S1—C1—C6	−140.4 (5)	C7—C8—C9—O4	−0.9 (8)
O2—S1—C1—C2	−72.5 (4)	N1—C8—C9—O4	−179.6 (5)
O3—S1—C1—C2	155.5 (4)	C7—C8—C9—N2	−179.5 (5)
N1—S1—C1—C2	41.0 (4)	N1—C8—C9—N2	1.9 (7)
C6—C1—C2—C3	−3.9 (8)	C9—N2—C10—C15	19.3 (8)
S1—C1—C2—C3	174.7 (4)	C9—N2—C10—C11	−160.5 (5)
C6—C1—C2—C7	173.4 (5)	C15—C10—C11—C12	−0.6 (7)
S1—C1—C2—C7	−8.0 (6)	N2—C10—C11—C12	179.2 (4)
C1—C2—C3—C4	2.4 (8)	C15—C10—C11—C16	178.9 (4)
C7—C2—C3—C4	−174.9 (5)	N2—C10—C11—C16	−1.3 (7)
C2—C3—C4—C5	0.7 (10)	C10—C11—C12—C13	−1.7 (8)
C3—C4—C5—C6	−2.4 (11)	C16—C11—C12—C13	178.8 (5)
C2—C1—C6—C5	2.2 (9)	C11—C12—C13—C14	2.2 (8)
S1—C1—C6—C5	−176.3 (5)	C12—C13—C14—C15	−0.2 (8)
C4—C5—C6—C1	0.9 (10)	C13—C14—C15—C10	−2.1 (8)
C3—C2—C7—O1	−20.1 (7)	N2—C10—C15—C14	−177.3 (5)
C1—C2—C7—O1	162.7 (5)	C11—C10—C15—C14	2.5 (7)
C3—C2—C7—C8	159.0 (5)	C12—C11—C16—O5	160.7 (5)
C1—C2—C7—C8	−18.2 (7)	C10—C11—C16—O5	−18.7 (8)
O1—C7—C8—N1	−178.8 (4)	C12—C11—C16—N3	−19.5 (7)
C2—C7—C8—N1	2.1 (7)	C10—C11—C16—N3	161.1 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.82	1.85	2.569 (5)	145
N2—H2···O5	0.86	1.92	2.607 (5)	136
N2—H2···N1	0.86	2.28	2.728 (5)	113
N3—H3A···O5ⁱ	0.86	2.22	2.941 (6)	141

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅N₃O₅S
M_r	373.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.1377 (6), 7.0515 (6), 29.069 (2)
β (°)	96.502 (3)
V (Å³)	1657.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.39 × 0.25 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.915, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	16109, 3753, 3011
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.213, 1.09
No. of reflections	3753
No. of parameters	237
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.40

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.8200	1.8500	2.569 (5)	145.00
N2—H2···O5	0.8600	1.9200	2.607 (5)	136.00
N2—H2···N1	0.8600	2.2800	2.728 (5)	113.00
N3—H3A···O5ⁱ	0.8600	2.2200	2.941 (6)	141.00

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors are grateful to the PCSIR Laboratories Complex, Lahore, for the provision of facilities necessary to complete this work.

References

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
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Volume 65| Part 10| October 2009| Page o2596

doi:10.1107/S1600536809038951

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N-[2-(Amino­carbon­yl)phen­yl]-4-hydr­­oxy-2-methyl-2H-1,2-benzo­thia­zine-3-carboxamide 1,1-dioxide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide