Piperidinium 4-hydr-oxy-3-methoxy-carbon-yl-1,2-benzothia-zin-2-ide 1,1-dioxide.

In the anion of the title compound, C(5)H(12)N(+)·C(10)H(8)NO(5)S(-), the thia-zine ring adopts a distorted half-chair conformation and the enolic H atom is involved in an intra-molecular O-H⋯O hydrogen bond, forming a six-membered ring. The anions and cations are connected via N-H⋯N and N-H⋯O inter-actions.

Related literature

For the synthesis of related mol­ecules, see: Zia-ur-Rehman et al. (2005 ▶, 2006 ▶); Braun (1923 ▶). For the biological activity of 1,2-benzothia­zine1,pan class="Chemical">1-dioxidesn>, see: Bihovsky et al. (2004 ▶); Turck et al. (1996 ▶); Zia-ur-Rehman et al. (2009 ▶). For related structures, see: Golič & Leban (1987 ▶).

Experimental

Crystal data

pan class="Chemical">C5H12Nn>+·pan class="Chemical">C10H8NO5S−

M = 340.39

Monoclinic,

a = 12.0423 (5) Å

b = 9.1791 (3) Å

c = 14.5193 (5) Å

β = 90.556 (2)°

V = 1604.85 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.39 × 0.33 × 0.29 mm

Data collection

Bruker KAPn class="Chemical">PA APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2007 ▶) T min = 0.921, T max = 0.940

16000 measured reflections

3690 independent reflections

2896 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.103

S = 1.03

3690 reflections

216 parameters

pan class="Disease">H atomsn> treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.34 e Å−3

Data collection: n class="Gene">APEX2n> (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.

Crystal structure: contains datablocks I, New_Global_pan class="Chemical">Pn>ubl_Block. DOI: 10.1107/S1600536809036204/bt5055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036204/bt5055Isup2.hkl

Additional supn class="Chemical">plementary materials: crystallographic information; 3D view; checkCIF report

C5H12N+·C10H8NO5S−	F(000) = 720
Mr = 340.39	Dx = 1.409 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6881 reflections
a = 12.0423 (5) Å	θ = 2.6–27.4°
b = 9.1791 (3) Å	µ = 0.23 mm−1
c = 14.5193 (5) Å	T = 296 K
β = 90.556 (2)°	Needle, white yellow
V = 1604.85 (10) Å3	0.39 × 0.33 × 0.29 mm
Z = 4

Bruker KAPPA APEXII CCD diffractometer	3690 independent reflections
Radiation source: fine-focus sealed tube	2896 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker 2007)	h = −15→15
Tmin = 0.921, Tmax = 0.940	k = −11→11
16000 measured reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0492P)2 + 0.5427P] where P = (Fo2 + 2Fc2)/3
3690 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.46805 (3)	0.74091 (4)	0.76725 (3)	0.02947 (12)
O1	0.48950 (11)	0.80132 (14)	0.85705 (8)	0.0461 (3)
O2	0.38877 (9)	0.62124 (13)	0.76755 (8)	0.0388 (3)
O3	0.51396 (13)	0.69087 (18)	0.47854 (8)	0.0570 (4)
H3	0.4706	0.7429	0.4497	0.085*
O4	0.36167 (13)	0.88585 (17)	0.45879 (8)	0.0598 (4)
O5	0.30030 (10)	1.00194 (13)	0.58304 (8)	0.0428 (3)
N1	0.33595 (12)	0.12173 (16)	0.77625 (10)	0.0354 (3)
H2N	0.2658 (17)	0.113 (2)	0.7631 (13)	0.042*
H1N	0.3719 (16)	0.041 (2)	0.7515 (13)	0.042*
N2	0.43544 (11)	0.86485 (14)	0.69844 (9)	0.0334 (3)
C1	0.59021 (13)	0.64809 (18)	0.62624 (12)	0.0358 (4)
C2	0.67446 (15)	0.5623 (2)	0.58853 (15)	0.0502 (5)
H2A	0.6768	0.5474	0.5252	0.060*
C3	0.75373 (15)	0.4998 (2)	0.64477 (17)	0.0576 (6)
H3A	0.8079	0.4405	0.6191	0.069*
C4	0.75421 (15)	0.5235 (2)	0.73845 (17)	0.0536 (5)
H4	0.8104	0.4843	0.7752	0.064*
C5	0.67134 (14)	0.60531 (19)	0.77759 (14)	0.0425 (4)
H5	0.6711	0.6216	0.8408	0.051*
C6	0.58827 (12)	0.66317 (17)	0.72195 (11)	0.0322 (3)
C7	0.50910 (14)	0.72383 (19)	0.56940 (11)	0.0359 (4)
C8	0.43901 (13)	0.82600 (18)	0.60482 (10)	0.0319 (3)
C9	0.36534 (14)	0.90591 (19)	0.54163 (11)	0.0366 (4)
C10	0.22478 (18)	1.0821 (2)	0.52354 (13)	0.0553 (5)
H10A	0.1749	1.0154	0.4934	0.083*
H10B	0.2664	1.1342	0.4781	0.083*
H10C	0.1829	1.1499	0.5597	0.083*
C11	0.37737 (15)	0.25674 (18)	0.73166 (12)	0.0396 (4)
H11A	0.3354	0.3399	0.7534	0.047*
H11B	0.3670	0.2498	0.6655	0.047*
C12	0.49815 (17)	0.2779 (2)	0.75380 (14)	0.0483 (5)
H12A	0.5242	0.3667	0.7249	0.058*
H12B	0.5404	0.1971	0.7292	0.058*
C13	0.51701 (19)	0.2874 (2)	0.85636 (15)	0.0592 (6)
H13A	0.4815	0.3743	0.8800	0.071*
H13B	0.5960	0.2945	0.8694	0.071*
C14	0.47016 (19)	0.1542 (2)	0.90404 (13)	0.0560 (5)
H14A	0.5143	0.0697	0.8880	0.067*
H14B	0.4758	0.1676	0.9702	0.067*
C15	0.35025 (17)	0.1258 (2)	0.87800 (13)	0.0517 (5)
H15A	0.3268	0.0336	0.9040	0.062*
H15B	0.3038	0.2020	0.9033	0.062*

	U11	U22	U33	U12	U13	U23
S1	0.0313 (2)	0.0288 (2)	0.0283 (2)	0.00206 (15)	−0.00296 (14)	0.00160 (15)
O1	0.0628 (8)	0.0457 (7)	0.0298 (6)	0.0067 (6)	−0.0103 (5)	−0.0026 (5)
O2	0.0301 (6)	0.0365 (6)	0.0498 (7)	−0.0018 (5)	0.0027 (5)	0.0071 (5)
O3	0.0690 (10)	0.0707 (10)	0.0313 (7)	0.0207 (8)	0.0058 (6)	−0.0064 (6)
O4	0.0770 (10)	0.0738 (10)	0.0285 (6)	0.0239 (8)	−0.0077 (6)	0.0021 (6)
O5	0.0503 (7)	0.0440 (7)	0.0339 (6)	0.0158 (6)	−0.0076 (5)	0.0031 (5)
N1	0.0295 (7)	0.0335 (8)	0.0431 (8)	0.0014 (6)	−0.0020 (6)	−0.0021 (6)
N2	0.0425 (7)	0.0295 (7)	0.0280 (6)	0.0070 (6)	−0.0034 (5)	−0.0003 (5)
C1	0.0305 (8)	0.0330 (8)	0.0439 (9)	−0.0015 (7)	0.0060 (7)	0.0023 (7)
C2	0.0409 (10)	0.0493 (11)	0.0606 (12)	0.0078 (9)	0.0150 (9)	−0.0001 (10)
C3	0.0320 (9)	0.0491 (12)	0.0918 (17)	0.0096 (9)	0.0121 (10)	0.0026 (11)
C4	0.0289 (9)	0.0453 (11)	0.0863 (16)	0.0027 (8)	−0.0118 (9)	0.0105 (11)
C5	0.0342 (8)	0.0358 (9)	0.0573 (11)	−0.0029 (7)	−0.0120 (8)	0.0066 (8)
C6	0.0258 (7)	0.0268 (8)	0.0438 (9)	−0.0035 (6)	−0.0018 (6)	0.0021 (7)
C7	0.0375 (9)	0.0401 (9)	0.0301 (8)	−0.0004 (7)	0.0038 (6)	0.0003 (7)
C8	0.0350 (8)	0.0322 (8)	0.0284 (7)	−0.0001 (7)	−0.0011 (6)	0.0022 (6)
C9	0.0417 (9)	0.0363 (9)	0.0317 (8)	−0.0004 (8)	−0.0021 (7)	0.0030 (7)
C10	0.0630 (13)	0.0602 (13)	0.0426 (10)	0.0239 (10)	−0.0116 (9)	0.0095 (9)
C11	0.0444 (9)	0.0312 (9)	0.0430 (9)	−0.0001 (7)	−0.0060 (7)	0.0015 (7)
C12	0.0467 (10)	0.0394 (10)	0.0589 (12)	−0.0109 (8)	−0.0033 (9)	0.0003 (9)
C13	0.0645 (14)	0.0474 (12)	0.0653 (13)	−0.0078 (10)	−0.0238 (11)	−0.0101 (10)
C14	0.0728 (14)	0.0560 (13)	0.0389 (10)	0.0058 (11)	−0.0160 (9)	−0.0044 (9)
C15	0.0611 (12)	0.0534 (12)	0.0409 (10)	0.0075 (10)	0.0129 (9)	0.0001 (9)

S1—O1	1.4379 (12)	C4—H4	0.9300
S1—O2	1.4554 (12)	C5—C6	1.385 (2)
S1—N2	1.5618 (13)	C5—H5	0.9300
S1—C6	1.7483 (16)	C7—C8	1.366 (2)
O3—C7	1.3553 (19)	C8—C9	1.467 (2)
O3—H3	0.8200	C10—H10A	0.9600
O4—C9	1.217 (2)	C10—H10B	0.9600
O5—C9	1.327 (2)	C10—H10C	0.9600
O5—C10	1.449 (2)	C11—C12	1.499 (3)
N1—C15	1.486 (2)	C11—H11A	0.9700
N1—C11	1.487 (2)	C11—H11B	0.9700
N1—H2N	0.87 (2)	C12—C13	1.507 (3)
N1—H1N	0.93 (2)	C12—H12A	0.9700
N2—C8	1.4063 (19)	C12—H12B	0.9700
C1—C6	1.397 (2)	C13—C14	1.516 (3)
C1—C2	1.400 (2)	C13—H13A	0.9700
C1—C7	1.450 (2)	C13—H13B	0.9700
C2—C3	1.375 (3)	C14—C15	1.512 (3)
C2—H2A	0.9300	C14—H14A	0.9700
C3—C4	1.377 (3)	C14—H14B	0.9700
C3—H3A	0.9300	C15—H15A	0.9700
C4—C5	1.376 (3)	C15—H15B	0.9700
O1—S1—O2	113.61 (8)	O4—C9—O5	122.16 (16)
O1—S1—N2	109.94 (7)	O4—C9—C8	123.95 (16)
O2—S1—N2	113.00 (7)	O5—C9—C8	113.88 (14)
O1—S1—C6	110.88 (8)	O5—C10—H10A	109.5
O2—S1—C6	103.81 (7)	O5—C10—H10B	109.5
N2—S1—C6	105.11 (7)	H10A—C10—H10B	109.5
C7—O3—H3	109.5	O5—C10—H10C	109.5
C9—O5—C10	115.92 (14)	H10A—C10—H10C	109.5
C15—N1—C11	112.06 (15)	H10B—C10—H10C	109.5
C15—N1—H2N	108.9 (12)	N1—C11—C12	110.10 (15)
C11—N1—H2N	108.1 (13)	N1—C11—H11A	109.6
C15—N1—H1N	110.7 (11)	C12—C11—H11A	109.6
C11—N1—H1N	109.6 (11)	N1—C11—H11B	109.6
H2N—N1—H1N	107.3 (17)	C12—C11—H11B	109.6
C8—N2—S1	115.08 (11)	H11A—C11—H11B	108.2
C6—C1—C2	117.64 (16)	C11—C12—C13	110.86 (17)
C6—C1—C7	120.06 (14)	C11—C12—H12A	109.5
C2—C1—C7	122.27 (17)	C13—C12—H12A	109.5
C3—C2—C1	120.25 (19)	C11—C12—H12B	109.5
C3—C2—H2A	119.9	C13—C12—H12B	109.5
C1—C2—H2A	119.9	H12A—C12—H12B	108.1
C2—C3—C4	121.11 (18)	C12—C13—C14	110.59 (16)
C2—C3—H3A	119.4	C12—C13—H13A	109.5
C4—C3—H3A	119.4	C14—C13—H13A	109.5
C5—C4—C3	119.85 (18)	C12—C13—H13B	109.5
C5—C4—H4	120.1	C14—C13—H13B	109.5
C3—C4—H4	120.1	H13A—C13—H13B	108.1
C4—C5—C6	119.40 (19)	C15—C14—C13	112.54 (17)
C4—C5—H5	120.3	C15—C14—H14A	109.1
C6—C5—H5	120.3	C13—C14—H14A	109.1
C5—C6—C1	121.54 (16)	C15—C14—H14B	109.1
C5—C6—S1	122.21 (14)	C13—C14—H14B	109.1
C1—C6—S1	115.89 (12)	H14A—C14—H14B	107.8
O3—C7—C8	123.54 (15)	N1—C15—C14	110.74 (15)
O3—C7—C1	114.31 (15)	N1—C15—H15A	109.5
C8—C7—C1	122.03 (15)	C14—C15—H15A	109.5
C7—C8—N2	124.26 (14)	N1—C15—H15B	109.5
C7—C8—C9	118.70 (14)	C14—C15—H15B	109.5
N2—C8—C9	116.99 (14)	H15A—C15—H15B	108.1
O1—S1—N2—C8	165.08 (12)	C2—C1—C7—O3	7.3 (2)
O2—S1—N2—C8	−66.84 (13)	C6—C1—C7—C8	9.0 (3)
C6—S1—N2—C8	45.69 (13)	C2—C1—C7—C8	−168.87 (17)
C6—C1—C2—C3	−2.0 (3)	O3—C7—C8—N2	−177.84 (16)
C7—C1—C2—C3	175.93 (18)	C1—C7—C8—N2	−2.0 (3)
C1—C2—C3—C4	−2.0 (3)	O3—C7—C8—C9	−0.5 (3)
C2—C3—C4—C5	3.1 (3)	C1—C7—C8—C9	175.28 (15)
C3—C4—C5—C6	−0.1 (3)	S1—N2—C8—C7	−29.7 (2)
C4—C5—C6—C1	−4.0 (3)	S1—N2—C8—C9	152.98 (12)
C4—C5—C6—S1	168.73 (14)	C10—O5—C9—O4	−0.2 (3)
C2—C1—C6—C5	5.0 (2)	C10—O5—C9—C8	−179.11 (16)
C7—C1—C6—C5	−172.97 (16)	C7—C8—C9—O4	0.8 (3)
C2—C1—C6—S1	−168.17 (13)	N2—C8—C9—O4	178.31 (17)
C7—C1—C6—S1	13.8 (2)	C7—C8—C9—O5	179.66 (15)
O1—S1—C6—C5	28.75 (16)	N2—C8—C9—O5	−2.8 (2)
O2—S1—C6—C5	−93.61 (15)	C15—N1—C11—C12	59.0 (2)
N2—S1—C6—C5	147.50 (14)	N1—C11—C12—C13	−58.6 (2)
O1—S1—C6—C1	−158.11 (12)	C11—C12—C13—C14	55.4 (2)
O2—S1—C6—C1	79.53 (13)	C12—C13—C14—C15	−52.5 (2)
N2—S1—C6—C1	−39.36 (14)	C11—N1—C15—C14	−55.5 (2)
C6—C1—C7—O3	−174.80 (15)	C13—C14—C15—N1	52.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.82	1.86	2.577 (2)	145
N1—H1N···N2i	0.932 (19)	1.951 (19)	2.881 (2)	175.4 (18)
N1—H2N···O2ii	0.87 (2)	1.91 (2)	2.7739 (18)	172.4 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.82	1.86	2.577 (2)	145
N1—H1N⋯N2i	0.932 (19)	1.951 (19)	2.881 (2)	175.4 (18)
N1—H2N⋯O2ii	0.87 (2)	1.91 (2)	2.7739 (18)	172.4 (18)

Symmetry codes: (i) ; (ii) .