4-Hy-droxy-2-[(4-iodo-benzo-yl)meth-yl]-3-(3-meth-oxy-benzo-yl)-2H-1,2-benzothia-zine 1,1-dioxide.

In the title mol-ecule, C(24)H(18)INO(6)S, the heterocyclic thia-zine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.381 (5) and -0.449 (5) Å, respectively, from the plane formed by the remaining atoms in the ring; the puckering parameters are Q = 0.550 (2) Å, θ = 61.7 (2)° and ϕ = 31.4 (3)°. The conformation is stabilized by an intra-molecular O-H⋯O hydrogen bond. The two nonfused benzene rings lie almost parallel to each other [dihedral angle = 9.18 (4)°], with a separation of 3.754 (2) Å between the centres of gravity of the two rings, indicating strong π-π inter-actions.

Related literature

For biological applications of benzothia­zines, see: Lombardino & Wiseman (1972 ▶); Zinnes et al. (1982 ▶); Zia-ur-Rehman et al. (2005 ▶); Turck et al. (1996 ▶); Ahmad et al. (2010 ▶). For crystal structures of related compounds, see: Siddiqui et al. (2008 ▶); Gul et al. (2010 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C24H18INO6S

M = 575.35

Monoclinic,

a = 9.7392 (2) Å

b = 11.5288 (3) Å

c = 20.4634 (4) Å

β = 100.5288 (11)°

V = 2258.97 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.55 mm−1

T = 173 K

0.12 × 0.10 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1997 ▶) T min = 0.836, T max = 0.886

16229 measured reflections

3960 independent reflections

3620 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.061

S = 1.08

3960 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.76 e Å−3

Δρmin = −0.83 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DEn class="Chemical">NZO (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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032265/pk2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032265/pk2258Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C24H18INO6S	F(000) = 1144
Mr = 575.35	Dx = 1.692 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5266 reflections
a = 9.7392 (2) Å	θ = 1.0–27.5°
b = 11.5288 (3) Å	µ = 1.55 mm−1
c = 20.4634 (4) Å	T = 173 K
β = 100.5288 (11)°	Prism, yellow
V = 2258.97 (9) Å3	0.12 × 0.10 × 0.08 mm
Z = 4

Nonius KappaCCD diffractometer	3960 independent reflections
Radiation source: fine-focus sealed tube	3620 reflections with I > 2σ(I)
graphite	Rint = 0.017
ω and φ scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
Tmin = 0.836, Tmax = 0.886	k = −13→13
16229 measured reflections	l = −24→24

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)] = 0.026	Hydrogen site location: difference Fourier map
wR(F2) = 0.061	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0174P)2 + 2.9397P] where P = (Fo2 + 2Fc2)/3
3960 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.76 e Å−3
0 restraints	Δρmin = −0.83 e Å−3

Experimental. Yield: 1.96 g, 70%, m.p. 413–414 K, IR (KBr, νmax): 2957, 1682, 1340, 1128 cm-1, EI–MS (m/z): 575.0

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
I1	0.309451 (19)	0.222186 (19)	0.434249 (8)	0.04263 (8)
S1	−0.12938 (6)	0.42205 (5)	0.72012 (3)	0.02558 (14)
O1	−0.15136 (17)	0.53974 (15)	0.69887 (9)	0.0335 (4)
O2	−0.18899 (17)	0.33084 (16)	0.67691 (9)	0.0330 (4)
O3	0.1160 (2)	0.56345 (19)	0.89527 (10)	0.0465 (5)
H3O	0.1921	0.5875	0.8867	0.070*
O4	0.30729 (19)	0.59168 (17)	0.82968 (11)	0.0448 (5)
O5	0.1389 (2)	0.5711 (2)	0.54065 (11)	0.0515 (6)
O6	0.33468 (18)	0.27269 (16)	0.77976 (9)	0.0310 (4)
N1	0.04075 (19)	0.40214 (17)	0.73891 (10)	0.0239 (4)
C1	−0.1770 (3)	0.4068 (2)	0.79852 (12)	0.0281 (5)
C2	−0.3034 (3)	0.3567 (2)	0.80468 (14)	0.0346 (6)
H2	−0.3641	0.3266	0.7668	0.042*
C3	−0.3395 (3)	0.3513 (3)	0.86691 (16)	0.0465 (7)
H3	−0.4260	0.3178	0.8720	0.056*
C4	−0.2503 (4)	0.3946 (3)	0.92140 (17)	0.0563 (9)
H4	−0.2765	0.3917	0.9639	0.068*
C5	−0.1229 (3)	0.4422 (3)	0.91516 (15)	0.0495 (8)
H5	−0.0621	0.4705	0.9535	0.059*
C6	−0.0831 (3)	0.4489 (2)	0.85358 (13)	0.0334 (6)
C7	0.0526 (3)	0.4997 (2)	0.84576 (14)	0.0343 (6)
C8	0.1083 (2)	0.4833 (2)	0.78869 (13)	0.0277 (5)
C9	0.2346 (3)	0.5410 (2)	0.78018 (15)	0.0350 (6)
C10	0.2832 (3)	0.5437 (2)	0.71554 (15)	0.0337 (6)
C11	0.1901 (3)	0.5553 (2)	0.65576 (15)	0.0359 (6)
H11	0.0927	0.5602	0.6556	0.043*
C12	0.2394 (3)	0.5599 (2)	0.59636 (16)	0.0403 (7)
C13	0.3816 (3)	0.5525 (3)	0.59645 (17)	0.0448 (7)
H13	0.4154	0.5543	0.5557	0.054*
C14	0.4742 (3)	0.5427 (3)	0.65634 (17)	0.0461 (8)
H14	0.5716	0.5386	0.6564	0.055*
C15	0.4271 (3)	0.5388 (2)	0.71568 (16)	0.0403 (7)
H15	0.4915	0.5328	0.7564	0.048*
C16	0.1815 (4)	0.5671 (4)	0.47757 (17)	0.0605 (10)
H16A	0.0988	0.5674	0.4422	0.073*
H16B	0.2355	0.4963	0.4745	0.073*
H16C	0.2394	0.6350	0.4727	0.073*
C17	0.0871 (3)	0.2799 (2)	0.75191 (12)	0.0251 (5)
H17A	0.0214	0.2265	0.7240	0.030*
H17B	0.0890	0.2602	0.7992	0.030*
C18	0.2332 (3)	0.2673 (2)	0.73533 (12)	0.0250 (5)
C19	0.2470 (3)	0.2523 (2)	0.66453 (12)	0.0256 (5)
C20	0.1333 (3)	0.2615 (2)	0.61251 (13)	0.0292 (6)
H20	0.0426	0.2741	0.6220	0.035*
C21	0.1508 (3)	0.2524 (2)	0.54714 (13)	0.0334 (6)
H21	0.0731	0.2603	0.5119	0.040*
C22	0.2828 (3)	0.2318 (2)	0.53356 (13)	0.0313 (6)
C23	0.3973 (3)	0.2196 (3)	0.58470 (14)	0.0355 (6)
H23	0.4872	0.2037	0.5750	0.043*
C24	0.3789 (3)	0.2308 (2)	0.64959 (13)	0.0320 (6)
H24	0.4572	0.2238	0.6847	0.038*

	U11	U22	U33	U12	U13	U23
I1	0.03981 (12)	0.06393 (15)	0.02580 (11)	−0.00825 (9)	0.01039 (8)	−0.00513 (8)
S1	0.0217 (3)	0.0240 (3)	0.0290 (3)	−0.0021 (2)	−0.0009 (2)	0.0009 (2)
O1	0.0263 (9)	0.0271 (9)	0.0435 (11)	0.0010 (7)	−0.0030 (8)	0.0076 (8)
O2	0.0305 (9)	0.0333 (10)	0.0335 (10)	−0.0090 (8)	0.0016 (8)	−0.0047 (8)
O3	0.0362 (11)	0.0499 (13)	0.0488 (12)	−0.0011 (10)	−0.0046 (9)	−0.0239 (10)
O4	0.0290 (10)	0.0373 (11)	0.0609 (13)	−0.0048 (8)	−0.0103 (9)	−0.0153 (10)
O5	0.0337 (10)	0.0716 (16)	0.0476 (13)	0.0016 (10)	0.0034 (9)	0.0235 (11)
O6	0.0295 (9)	0.0363 (10)	0.0248 (9)	0.0047 (8)	−0.0017 (8)	0.0009 (8)
N1	0.0211 (10)	0.0205 (10)	0.0281 (11)	−0.0006 (8)	−0.0011 (8)	−0.0003 (8)
C1	0.0288 (13)	0.0257 (13)	0.0294 (13)	0.0046 (10)	0.0040 (10)	0.0006 (10)
C2	0.0311 (13)	0.0314 (15)	0.0417 (15)	0.0026 (11)	0.0074 (12)	0.0027 (12)
C3	0.0421 (16)	0.0507 (19)	0.0509 (18)	0.0010 (15)	0.0194 (14)	0.0049 (15)
C4	0.062 (2)	0.072 (2)	0.0396 (17)	0.0041 (18)	0.0203 (16)	0.0002 (17)
C5	0.0495 (18)	0.061 (2)	0.0362 (16)	0.0040 (16)	0.0044 (14)	−0.0104 (15)
C6	0.0328 (13)	0.0322 (15)	0.0341 (14)	0.0061 (11)	0.0029 (11)	−0.0045 (11)
C7	0.0291 (13)	0.0288 (14)	0.0403 (15)	0.0056 (11)	−0.0066 (11)	−0.0076 (12)
C8	0.0231 (12)	0.0223 (12)	0.0340 (14)	0.0038 (10)	−0.0048 (10)	−0.0031 (11)
C9	0.0256 (13)	0.0203 (13)	0.0540 (17)	0.0053 (10)	−0.0059 (12)	−0.0003 (12)
C10	0.0239 (12)	0.0187 (13)	0.0559 (17)	−0.0031 (10)	0.0004 (12)	0.0030 (12)
C11	0.0221 (12)	0.0288 (14)	0.0542 (17)	−0.0044 (11)	0.0001 (12)	0.0113 (13)
C12	0.0321 (14)	0.0317 (15)	0.0551 (18)	−0.0028 (12)	0.0030 (13)	0.0171 (13)
C13	0.0318 (14)	0.0421 (17)	0.062 (2)	−0.0022 (13)	0.0123 (14)	0.0108 (15)
C14	0.0235 (13)	0.0397 (17)	0.074 (2)	−0.0025 (12)	0.0065 (14)	0.0071 (16)
C15	0.0230 (13)	0.0295 (15)	0.063 (2)	−0.0016 (11)	−0.0053 (13)	0.0036 (14)
C16	0.0512 (19)	0.078 (3)	0.053 (2)	0.0050 (18)	0.0125 (16)	0.0238 (19)
C17	0.0303 (13)	0.0198 (12)	0.0252 (12)	0.0014 (10)	0.0049 (10)	−0.0005 (10)
C18	0.0303 (13)	0.0178 (12)	0.0262 (13)	0.0029 (10)	0.0033 (11)	0.0017 (10)
C19	0.0270 (12)	0.0248 (13)	0.0239 (12)	0.0013 (10)	0.0019 (10)	0.0019 (10)
C20	0.0249 (12)	0.0365 (15)	0.0259 (13)	−0.0008 (11)	0.0035 (10)	0.0013 (11)
C21	0.0265 (13)	0.0463 (16)	0.0254 (13)	−0.0035 (12)	−0.0007 (10)	0.0014 (12)
C22	0.0337 (14)	0.0378 (15)	0.0230 (13)	−0.0045 (12)	0.0072 (11)	−0.0024 (11)
C23	0.0260 (13)	0.0472 (17)	0.0335 (15)	0.0013 (12)	0.0063 (11)	−0.0031 (13)
C24	0.0257 (13)	0.0403 (16)	0.0277 (14)	0.0034 (11)	−0.0014 (10)	−0.0014 (11)

I1—C22	2.098 (3)	C10—C11	1.389 (4)
S1—O2	1.4272 (18)	C10—C15	1.402 (4)
S1—O1	1.4290 (18)	C11—C12	1.387 (4)
S1—N1	1.6472 (19)	C11—H11	0.9500
S1—C1	1.758 (3)	C12—C13	1.388 (4)
O3—C7	1.311 (3)	C13—C14	1.387 (4)
O3—H3O	0.8400	C13—H13	0.9500
O4—C9	1.267 (3)	C14—C15	1.375 (4)
O5—C12	1.366 (4)	C14—H14	0.9500
O5—C16	1.427 (4)	C15—H15	0.9500
O6—C18	1.216 (3)	C16—H16A	0.9800
N1—C8	1.450 (3)	C16—H16B	0.9800
N1—C17	1.489 (3)	C16—H16C	0.9800
C1—C2	1.386 (4)	C17—C18	1.530 (3)
C1—C6	1.402 (4)	C17—H17A	0.9900
C2—C3	1.383 (4)	C17—H17B	0.9900
C2—H2	0.9500	C18—C19	1.489 (3)
C3—C4	1.376 (5)	C19—C20	1.393 (3)
C3—H3	0.9500	C19—C24	1.396 (4)
C4—C5	1.383 (5)	C20—C21	1.383 (4)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.387 (4)	C21—C22	1.384 (4)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.480 (4)	C22—C23	1.390 (4)
C7—C8	1.388 (4)	C23—C24	1.378 (4)
C8—C9	1.437 (4)	C23—H23	0.9500
C9—C10	1.484 (4)	C24—H24	0.9500
O2—S1—O1	119.32 (11)	O5—C12—C13	124.7 (3)
O2—S1—N1	108.66 (10)	C11—C12—C13	120.1 (3)
O1—S1—N1	106.96 (10)	C14—C13—C12	119.6 (3)
O2—S1—C1	110.27 (12)	C14—C13—H13	120.2
O1—S1—C1	108.82 (12)	C12—C13—H13	120.2
N1—S1—C1	101.24 (11)	C15—C14—C13	121.0 (3)
C7—O3—H3O	109.5	C15—C14—H14	119.5
C12—O5—C16	118.0 (2)	C13—C14—H14	119.5
C8—N1—C17	113.69 (18)	C14—C15—C10	119.5 (3)
C8—N1—S1	112.47 (15)	C14—C15—H15	120.3
C17—N1—S1	115.63 (15)	C10—C15—H15	120.3
C2—C1—C6	122.1 (2)	O5—C16—H16A	109.5
C2—C1—S1	120.8 (2)	O5—C16—H16B	109.5
C6—C1—S1	117.17 (19)	H16A—C16—H16B	109.5
C3—C2—C1	118.8 (3)	O5—C16—H16C	109.5
C3—C2—H2	120.6	H16A—C16—H16C	109.5
C1—C2—H2	120.6	H16B—C16—H16C	109.5
C4—C3—C2	120.0 (3)	N1—C17—C18	108.30 (19)
C4—C3—H3	120.0	N1—C17—H17A	110.0
C2—C3—H3	120.0	C18—C17—H17A	110.0
C3—C4—C5	120.9 (3)	N1—C17—H17B	110.0
C3—C4—H4	119.6	C18—C17—H17B	110.0
C5—C4—H4	119.6	H17A—C17—H17B	108.4
C4—C5—C6	120.7 (3)	O6—C18—C19	121.9 (2)
C4—C5—H5	119.6	O6—C18—C17	119.4 (2)
C6—C5—H5	119.6	C19—C18—C17	118.7 (2)
C5—C6—C1	117.5 (3)	C20—C19—C24	118.7 (2)
C5—C6—C7	121.6 (3)	C20—C19—C18	122.3 (2)
C1—C6—C7	120.9 (2)	C24—C19—C18	118.9 (2)
O3—C7—C8	121.7 (2)	C21—C20—C19	120.8 (2)
O3—C7—C6	116.2 (2)	C21—C20—H20	119.6
C8—C7—C6	122.1 (2)	C19—C20—H20	119.6
C7—C8—C9	120.9 (2)	C20—C21—C22	119.4 (2)
C7—C8—N1	118.8 (2)	C20—C21—H21	120.3
C9—C8—N1	120.2 (2)	C22—C21—H21	120.3
O4—C9—C8	118.8 (3)	C21—C22—C23	120.9 (2)
O4—C9—C10	118.7 (2)	C21—C22—I1	119.18 (19)
C8—C9—C10	122.5 (2)	C23—C22—I1	119.96 (19)
C11—C10—C15	119.8 (3)	C24—C23—C22	119.2 (2)
C11—C10—C9	121.6 (2)	C24—C23—H23	120.4
C15—C10—C9	118.6 (3)	C22—C23—H23	120.4
C12—C11—C10	120.1 (2)	C23—C24—C19	121.0 (2)
C12—C11—H11	120.0	C23—C24—H24	119.5
C10—C11—H11	120.0	C19—C24—H24	119.5
O5—C12—C11	115.2 (2)
O2—S1—N1—C8	−173.39 (16)	C7—C8—C9—C10	−168.2 (2)
O1—S1—N1—C8	56.56 (19)	N1—C8—C9—C10	14.9 (4)
C1—S1—N1—C8	−57.30 (19)	O4—C9—C10—C11	−141.7 (3)
O2—S1—N1—C17	−40.51 (19)	C8—C9—C10—C11	38.2 (4)
O1—S1—N1—C17	−170.56 (17)	O4—C9—C10—C15	35.8 (4)
C1—S1—N1—C17	75.58 (18)	C8—C9—C10—C15	−144.3 (3)
O2—S1—C1—C2	−30.4 (2)	C15—C10—C11—C12	1.2 (4)
O1—S1—C1—C2	102.2 (2)	C9—C10—C11—C12	178.7 (3)
N1—S1—C1—C2	−145.3 (2)	C16—O5—C12—C11	−175.2 (3)
O2—S1—C1—C6	150.53 (19)	C16—O5—C12—C13	4.5 (4)
O1—S1—C1—C6	−76.8 (2)	C10—C11—C12—O5	179.8 (2)
N1—S1—C1—C6	35.6 (2)	C10—C11—C12—C13	0.1 (4)
C6—C1—C2—C3	2.0 (4)	O5—C12—C13—C14	179.2 (3)
S1—C1—C2—C3	−177.0 (2)	C11—C12—C13—C14	−1.1 (4)
C1—C2—C3—C4	−0.4 (5)	C12—C13—C14—C15	0.7 (5)
C2—C3—C4—C5	−1.0 (5)	C13—C14—C15—C10	0.6 (4)
C3—C4—C5—C6	0.9 (5)	C11—C10—C15—C14	−1.6 (4)
C4—C5—C6—C1	0.6 (5)	C9—C10—C15—C14	−179.2 (3)
C4—C5—C6—C7	179.9 (3)	C8—N1—C17—C18	−74.6 (2)
C2—C1—C6—C5	−2.0 (4)	S1—N1—C17—C18	153.04 (16)
S1—C1—C6—C5	177.0 (2)	N1—C17—C18—O6	97.6 (3)
C2—C1—C6—C7	178.7 (2)	N1—C17—C18—C19	−80.6 (3)
S1—C1—C6—C7	−2.3 (3)	O6—C18—C19—C20	−171.2 (2)
C5—C6—C7—O3	−16.8 (4)	C17—C18—C19—C20	6.9 (3)
C1—C6—C7—O3	162.5 (2)	O6—C18—C19—C24	7.4 (4)
C5—C6—C7—C8	164.7 (3)	C17—C18—C19—C24	−174.5 (2)
C1—C6—C7—C8	−16.0 (4)	C24—C19—C20—C21	−1.6 (4)
O3—C7—C8—C9	−3.4 (4)	C18—C19—C20—C21	177.0 (2)
C6—C7—C8—C9	175.0 (2)	C19—C20—C21—C22	1.3 (4)
O3—C7—C8—N1	173.5 (2)	C20—C21—C22—C23	0.3 (4)
C6—C7—C8—N1	−8.0 (4)	C20—C21—C22—I1	−178.5 (2)
C17—N1—C8—C7	−85.5 (3)	C21—C22—C23—C24	−1.4 (4)
S1—N1—C8—C7	48.3 (3)	I1—C22—C23—C24	177.4 (2)
C17—N1—C8—C9	91.4 (3)	C22—C23—C24—C19	1.0 (4)
S1—N1—C8—C9	−134.7 (2)	C20—C19—C24—C23	0.5 (4)
C7—C8—C9—O4	11.6 (4)	C18—C19—C24—C23	−178.2 (2)
N1—C8—C9—O4	−165.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O4	0.84	1.76	2.509 (3)	147
C11—H11···N1	0.95	2.61	3.006 (3)	106
C17—H17A···O2	0.99	2.42	2.902 (3)	109

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O4	0.84	1.76	2.509 (3)	147