Isoprop­yl (3,4-dimethyl-5,5-dioxo-4H-pyrazolo­[4,3-c][1,2]benzothia­zin-2-yl)acetate

Aslam, S.; Ahmad, M.; Siddiqui, H.L.; Parvez, M.

doi:10.1107/S1600536810037797

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2630

doi:10.1107/S1600536810037797

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Isopropyl (3,4-dimethyl-5,5-dioxo-4H-pyrazolo[4,3-c][1,2]benzothiazin-2-yl)acetate

Sana Aslam,^a Matloob Ahmad,^a,^b Hamid Latif Siddiqui ^a ^* and Masood Parvez ^c

^aInstitute of Chemistry, University of the Punjab, Lahore 54590, Pakistan, ^bApplied Chemistry Research Centre, PCSIR Laboratories Complex, Lahore 54600, 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 20 September 2010; accepted 21 September 2010; online 25 September 2010)

In the title molecule, C₁₆H₁₉N₃O₄S, the heterocyclic thiazine ring adopts a half-chair conformation, with the S and N atoms displaced by 0.547 (2) and −0.254 (3) Å, respectively, from the plane formed by the remaining atoms. In the crystal, weak C—H⋯N and C—H⋯O hydrogen bonds link the molecules.

Related literature

For the biological applications of benzothiazines, see: Shavel et al. (1968 ); Krapcho (1969 ); Lombardino & Wiseman (1972 ); Kwon & Park (1996 ); Wells et al. (2001 ); Zia-ur-Rehman et al. (2006 ); Ahmad et al. (2010 ). For related structures, see: Siddiqui et al. (2008 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₉N₃O₄S
M_r = 349.40
Triclinic, $[P \overline 1]$
a = 7.6370 (2) Å
b = 8.5412 (2) Å
c = 13.3096 (4) Å
α = 98.4584 (18)°
β = 97.4870 (13)°
γ = 95.9599 (17)°
V = 844.69 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 173 K
0.18 × 0.16 × 0.11 mm

Data collection

Nonius Kappa CCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.962, T_max = 0.977
12392 measured reflections
3824 independent reflections
3552 reflections with I > 2.0σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.095
S = 1.04
3824 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.95	2.54	3.4015 (17)	150
C12—H12A⋯N2ⁱⁱ	0.99	2.50	3.4413 (17)	158
C12—H12B⋯O1ⁱⁱⁱ	0.99	2.51	3.4694 (17)	163
C15—H15B⋯O3^iv	0.98	2.53	3.456 (2)	157
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y, -z+2; (iv) -x, -y+1, -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/S1600536810037797/hb5643sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810037797/hb5643Isup2.hkl

checkCIF report

Comment top

Important anti-inflammatory and analgesic properties of 4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxides (Oxicams) (Lombardino & Wiseman, 1972; Kwon & Park, 1996) boosted research interests in benzothiazines. These studies led to discovery of a wide range of benzothiazine derivatives having potential biological activities, such as inhibitors of calpain I belonging to a family of calcium-dependent, non-lysosomal cysteine proteases (proteolytic enzymes) (Wells et al., 2001), antifungal (Shavel et al., 1968) and antibacterial agents (Zia-ur-Rehman et al., 2006), central nervous system depressants (drugs used to slow down brain activity and are used to treat anxiety, muscle tension, pain, insomnia, acute stress reactions, panic attacks and seizure disorders), tranquilizers (Krapcho, 1969) as well as antioxidants (Ahmad et al., 2010).

In the title molecule (Fig. 1), the heterocyclic thiazine ring adopts a half-chair conformation, with atoms S1 and N1 displaced from the plane C1\C6\C7\C8 by 0.547 (2) and -0.254 (3) Å, respectively. The pertinent puckering parameters (Cremer & Pople, 1975) are: Q = 0.5288 (10) Å, θ = 63.93 (13)° and ϕ = 19.41 (16)°. Similar conformations of the corresponding rings have been reported in some closely related molecules (Siddiqui et al., 2008). The intermolecular interactions of the type C—H···N and C—H···O are listed in Tab. 1.

Related literature top

For the biological applications of benzothiazines, see: Shavel et al. (1968); Krapcho (1969); Lombardino & Wiseman (1972); Kwon & Park (1996); Wells et al. (2001); Zia-ur-Rehman et al. (2006); Ahmad et al. (2010). For related structures, see: Siddiqui et al. (2008). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 3,4-dimethyl-2,4-dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide (5.00 g, 0.020 mol), anhydrous potassium carbonate (3.31 g, 0.024 mol), isopropyl chloroacetate (3.28 g, 0.024 mol) and acetonitrile (30 ml) was refluxed for 10 h at 355 K, i. e. at the boiling point of acetonitrile. The completion of reaction was monitored by thin layer chromatography (TLC). After completion of the reaction the solvent was removed under vacuum. The residue was washed with cold water to obtain the title compound as a white crystalline product. Yellow prisms of (I) of approximate size 0.10–0.30 mm were grown from a solution of 0.5 g of the title compound dissolved in 15 ml mixture of methanol and chloroform (1:1); the methanol contained 0.5% of moisture. Yield of the recrystallised product : 80%

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. The title molecule with the displacement ellipsoids at the 50% probability level.

Isopropyl 2-(3,4-dimethyl-5,5-dioxo-4H-pyrazolo[4,3-c][1,2]benzothiazin- 2-yl)acetate top

Crystal data top

C₁₆H₁₉N₃O₄S	Z = 2
M_r = 349.40	F(000) = 368
Triclinic, P1	D_x = 1.374 Mg m⁻³
Hall symbol: -P 1	Melting point = 453–455 K
a = 7.6370 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5412 (2) Å	Cell parameters from 3658 reflections
c = 13.3096 (4) Å	θ = 1.0–27.5°
α = 98.4584 (18)°	µ = 0.22 mm⁻¹
β = 97.4870 (13)°	T = 173 K
γ = 95.9599 (17)°	Prism, yellow
V = 844.69 (4) Å³	0.18 × 0.16 × 0.11 mm

Data collection top

Nonius Kappa CCD diffractometer	3824 independent reflections
Radiation source: fine-focus sealed tube	3552 reflections with I > 2.0σ(I)
Graphite monochromator	R_int = 0.017
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.7°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −9→9
T_min = 0.962, T_max = 0.977	k = −11→11
12392 measured reflections	l = −17→17

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F²) = 0.095	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0415P)² + 0.4374P] where P = (F_o² + 2F_c²)/3
3824 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³
72 constraints

Crystal data top

C₁₆H₁₉N₃O₄S	γ = 95.9599 (17)°
M_r = 349.40	V = 844.69 (4) Å³
Triclinic, P1	Z = 2
a = 7.6370 (2) Å	Mo Kα radiation
b = 8.5412 (2) Å	µ = 0.22 mm⁻¹
c = 13.3096 (4) Å	T = 173 K
α = 98.4584 (18)°	0.18 × 0.16 × 0.11 mm
β = 97.4870 (13)°

Data collection top

Nonius Kappa CCD diffractometer	3824 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	3552 reflections with I > 2.0σ(I)
T_min = 0.962, T_max = 0.977	R_int = 0.017
12392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.04	Δρ_max = 0.38 e Å⁻³
3824 reflections	Δρ_min = −0.38 e Å⁻³
221 parameters

Special details top

Experimental. Analysis of the title compound by EI (electron impact) and MS (mass spectrometry): EI—MS (m/z, i. e. mass to charge ratio): 349.1

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.35224 (5)	−0.09565 (4)	0.67475 (2)	0.02666 (11)
O1	0.53320 (15)	−0.09803 (13)	0.71900 (8)	0.0344 (3)
O2	0.26989 (18)	−0.21974 (12)	0.59324 (8)	0.0400 (3)
O3	0.07421 (14)	0.34287 (14)	1.06534 (8)	0.0343 (2)
O4	0.25929 (13)	0.47365 (12)	1.20503 (7)	0.0266 (2)
N1	0.23204 (16)	−0.09429 (13)	0.76983 (8)	0.0248 (2)
N2	0.38590 (15)	0.30879 (13)	0.90139 (8)	0.0220 (2)
N3	0.35630 (15)	0.22831 (13)	0.97981 (8)	0.0211 (2)
C1	0.33526 (18)	0.09155 (15)	0.63524 (10)	0.0228 (3)
C2	0.3215 (2)	0.10488 (17)	0.53157 (10)	0.0280 (3)
H2	0.3125	0.0127	0.4808	0.034*
C3	0.3213 (2)	0.25514 (18)	0.50375 (11)	0.0290 (3)
H3	0.3141	0.2664	0.4334	0.035*
C4	0.33137 (19)	0.38921 (17)	0.57839 (10)	0.0266 (3)
H4	0.3320	0.4917	0.5587	0.032*
C5	0.34052 (18)	0.37494 (15)	0.68136 (10)	0.0234 (3)
H5	0.3450	0.4674	0.7315	0.028*
C6	0.34316 (17)	0.22555 (15)	0.71176 (9)	0.0204 (2)
C7	0.34179 (17)	0.19804 (15)	0.81758 (9)	0.0200 (2)
C8	0.28614 (17)	0.04849 (14)	0.84320 (9)	0.0199 (2)
C9	0.29516 (17)	0.07097 (15)	0.94854 (9)	0.0202 (2)
C10	0.25095 (18)	−0.04193 (16)	1.01953 (10)	0.0244 (3)
H10A	0.2407	−0.1518	0.9834	0.037*
H10B	0.1377	−0.0222	1.0431	0.037*
H10C	0.3454	−0.0260	1.0788	0.037*
C11	0.0369 (2)	−0.13282 (19)	0.73806 (13)	0.0377 (4)
H11A	−0.0216	−0.1382	0.7990	0.057*
H11B	0.0111	−0.2360	0.6923	0.057*
H11C	−0.0077	−0.0497	0.7019	0.057*
C12	0.38752 (18)	0.31656 (15)	1.08332 (9)	0.0226 (3)
H12A	0.4809	0.4079	1.0880	0.027*
H12B	0.4313	0.2466	1.1316	0.027*
C13	0.21988 (18)	0.37767 (15)	1.11442 (9)	0.0218 (3)
C14	0.11863 (18)	0.56384 (16)	1.24023 (10)	0.0244 (3)
H14	0.0006	0.4963	1.2204	0.029*
C15	0.1178 (2)	0.71022 (19)	1.18913 (13)	0.0372 (3)
H15A	0.0255	0.7727	1.2119	0.056*
H15B	0.0933	0.6778	1.1144	0.056*
H15C	0.2343	0.7753	1.2079	0.056*
C16	0.1623 (2)	0.6019 (2)	1.35555 (11)	0.0361 (3)
H16A	0.0724	0.6629	1.3830	0.054*
H16B	0.2798	0.6651	1.3747	0.054*
H16C	0.1632	0.5024	1.3840	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0442 (2)	0.01991 (17)	0.01619 (16)	0.01115 (14)	0.00383 (13)	−0.00046 (12)
O1	0.0450 (6)	0.0374 (6)	0.0255 (5)	0.0218 (5)	0.0079 (4)	0.0062 (4)
O2	0.0736 (8)	0.0228 (5)	0.0202 (5)	0.0096 (5)	0.0019 (5)	−0.0054 (4)
O3	0.0281 (5)	0.0419 (6)	0.0263 (5)	−0.0015 (4)	0.0008 (4)	−0.0087 (4)
O4	0.0284 (5)	0.0302 (5)	0.0182 (4)	0.0082 (4)	−0.0001 (4)	−0.0060 (4)
N1	0.0368 (6)	0.0175 (5)	0.0177 (5)	0.0010 (4)	0.0021 (4)	−0.0018 (4)
N2	0.0290 (6)	0.0198 (5)	0.0163 (5)	0.0003 (4)	0.0044 (4)	0.0011 (4)
N3	0.0277 (5)	0.0197 (5)	0.0145 (5)	0.0004 (4)	0.0042 (4)	−0.0006 (4)
C1	0.0296 (7)	0.0217 (6)	0.0172 (6)	0.0072 (5)	0.0028 (5)	0.0015 (5)
C2	0.0383 (8)	0.0281 (7)	0.0171 (6)	0.0100 (6)	0.0028 (5)	−0.0005 (5)
C3	0.0368 (8)	0.0342 (7)	0.0178 (6)	0.0101 (6)	0.0037 (5)	0.0063 (5)
C4	0.0311 (7)	0.0264 (7)	0.0233 (6)	0.0056 (5)	0.0027 (5)	0.0071 (5)
C5	0.0272 (6)	0.0210 (6)	0.0209 (6)	0.0025 (5)	0.0027 (5)	0.0009 (5)
C6	0.0216 (6)	0.0222 (6)	0.0166 (6)	0.0027 (5)	0.0024 (4)	0.0010 (5)
C7	0.0235 (6)	0.0186 (6)	0.0173 (6)	0.0032 (5)	0.0033 (5)	0.0003 (4)
C8	0.0245 (6)	0.0176 (6)	0.0168 (6)	0.0028 (5)	0.0034 (5)	−0.0004 (4)
C9	0.0221 (6)	0.0193 (6)	0.0183 (6)	0.0025 (4)	0.0030 (5)	0.0004 (4)
C10	0.0284 (7)	0.0242 (6)	0.0205 (6)	0.0006 (5)	0.0041 (5)	0.0050 (5)
C11	0.0412 (9)	0.0314 (8)	0.0333 (8)	−0.0118 (6)	−0.0001 (7)	−0.0021 (6)
C12	0.0280 (6)	0.0230 (6)	0.0147 (6)	0.0017 (5)	0.0021 (5)	−0.0017 (5)
C13	0.0294 (7)	0.0198 (6)	0.0148 (6)	−0.0004 (5)	0.0030 (5)	0.0014 (4)
C14	0.0255 (6)	0.0270 (6)	0.0201 (6)	0.0064 (5)	0.0040 (5)	−0.0007 (5)
C15	0.0422 (9)	0.0327 (8)	0.0389 (8)	0.0111 (6)	0.0045 (7)	0.0096 (6)
C16	0.0431 (9)	0.0434 (9)	0.0209 (7)	0.0126 (7)	0.0056 (6)	−0.0033 (6)

Geometric parameters (Å, º) top

S1—O2	1.4288 (11)	C6—C7	1.4628 (17)
S1—O1	1.4333 (12)	C7—C8	1.4077 (17)
S1—N1	1.6567 (12)	C8—C9	1.3784 (17)
S1—C1	1.7670 (13)	C9—C10	1.4901 (17)
O3—C13	1.1990 (17)	C10—H10A	0.9800
O4—C13	1.3343 (15)	C10—H10B	0.9800
O4—C14	1.4710 (16)	C10—H10C	0.9800
N1—C8	1.4323 (15)	C11—H11A	0.9800
N1—C11	1.484 (2)	C11—H11B	0.9800
N2—C7	1.3335 (16)	C11—H11C	0.9800
N2—N3	1.3613 (15)	C12—C13	1.5153 (19)
N3—C9	1.3608 (16)	C12—H12A	0.9900
N3—C12	1.4473 (15)	C12—H12B	0.9900
C1—C2	1.3924 (18)	C14—C16	1.5066 (19)
C1—C6	1.4062 (17)	C14—C15	1.509 (2)
C2—C3	1.387 (2)	C14—H14	1.0000
C2—H2	0.9500	C15—H15A	0.9800
C3—C4	1.390 (2)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.3870 (18)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.3955 (18)	C16—H16C	0.9800
C5—H5	0.9500

O2—S1—O1	119.34 (7)	C8—C9—C10	131.29 (12)
O2—S1—N1	108.09 (7)	C9—C10—H10A	109.5
O1—S1—N1	106.69 (6)	C9—C10—H10B	109.5
O2—S1—C1	109.45 (6)	H10A—C10—H10B	109.5
O1—S1—C1	108.09 (7)	C9—C10—H10C	109.5
N1—S1—C1	104.11 (6)	H10A—C10—H10C	109.5
C13—O4—C14	117.22 (10)	H10B—C10—H10C	109.5
C8—N1—C11	114.81 (11)	N1—C11—H11A	109.5
C8—N1—S1	109.87 (9)	N1—C11—H11B	109.5
C11—N1—S1	115.46 (10)	H11A—C11—H11B	109.5
C7—N2—N3	103.99 (10)	N1—C11—H11C	109.5
C9—N3—N2	113.73 (10)	H11A—C11—H11C	109.5
C9—N3—C12	128.00 (11)	H11B—C11—H11C	109.5
N2—N3—C12	118.25 (10)	N3—C12—C13	111.71 (11)
C2—C1—C6	121.72 (12)	N3—C12—H12A	109.3
C2—C1—S1	120.34 (10)	C13—C12—H12A	109.3
C6—C1—S1	117.89 (10)	N3—C12—H12B	109.3
C3—C2—C1	118.87 (13)	C13—C12—H12B	109.3
C3—C2—H2	120.6	H12A—C12—H12B	107.9
C1—C2—H2	120.6	O3—C13—O4	125.56 (13)
C2—C3—C4	120.23 (13)	O3—C13—C12	124.87 (12)
C2—C3—H3	119.9	O4—C13—C12	109.56 (11)
C4—C3—H3	119.9	O4—C14—C16	106.21 (11)
C5—C4—C3	120.70 (13)	O4—C14—C15	108.03 (12)
C5—C4—H4	119.7	C16—C14—C15	113.37 (13)
C3—C4—H4	119.7	O4—C14—H14	109.7
C4—C5—C6	120.35 (12)	C16—C14—H14	109.7
C4—C5—H5	119.8	C15—C14—H14	109.7
C6—C5—H5	119.8	C14—C15—H15A	109.5
C5—C6—C1	118.10 (12)	C14—C15—H15B	109.5
C5—C6—C7	124.07 (11)	H15A—C15—H15B	109.5
C1—C6—C7	117.70 (11)	C14—C15—H15C	109.5
N2—C7—C8	111.10 (11)	H15A—C15—H15C	109.5
N2—C7—C6	125.65 (11)	H15B—C15—H15C	109.5
C8—C7—C6	123.21 (11)	C14—C16—H16A	109.5
C9—C8—C7	106.45 (11)	C14—C16—H16B	109.5
C9—C8—N1	129.33 (11)	H16A—C16—H16B	109.5
C7—C8—N1	124.21 (11)	C14—C16—H16C	109.5
N3—C9—C8	104.72 (11)	H16A—C16—H16C	109.5
N3—C9—C10	123.98 (11)	H16B—C16—H16C	109.5

O2—S1—N1—C8	−167.41 (9)	C1—C6—C7—N2	164.83 (13)
O1—S1—N1—C8	63.09 (10)	C5—C6—C7—C8	158.23 (13)
C1—S1—N1—C8	−51.10 (10)	C1—C6—C7—C8	−17.56 (19)
O2—S1—N1—C11	−35.64 (12)	N2—C7—C8—C9	0.78 (15)
O1—S1—N1—C11	−165.14 (10)	C6—C7—C8—C9	−177.14 (12)
C1—S1—N1—C11	80.68 (11)	N2—C7—C8—N1	−179.36 (12)
C7—N2—N3—C9	−0.01 (14)	C6—C7—C8—N1	2.7 (2)
C7—N2—N3—C12	−178.48 (11)	C11—N1—C8—C9	83.07 (17)
O2—S1—C1—C2	−26.58 (14)	S1—N1—C8—C9	−144.81 (12)
O1—S1—C1—C2	104.88 (12)	C11—N1—C8—C7	−96.76 (15)
N1—S1—C1—C2	−141.94 (12)	S1—N1—C8—C7	35.36 (16)
O2—S1—C1—C6	155.87 (11)	N2—N3—C9—C8	0.48 (15)
O1—S1—C1—C6	−72.67 (12)	C12—N3—C9—C8	178.77 (12)
N1—S1—C1—C6	40.51 (12)	N2—N3—C9—C10	−179.31 (12)
C6—C1—C2—C3	2.0 (2)	C12—N3—C9—C10	−1.0 (2)
S1—C1—C2—C3	−175.44 (11)	C7—C8—C9—N3	−0.72 (14)
C1—C2—C3—C4	−1.1 (2)	N1—C8—C9—N3	179.42 (13)
C2—C3—C4—C5	−0.5 (2)	C7—C8—C9—C10	179.05 (13)
C3—C4—C5—C6	1.2 (2)	N1—C8—C9—C10	−0.8 (2)
C4—C5—C6—C1	−0.4 (2)	C9—N3—C12—C13	−85.83 (16)
C4—C5—C6—C7	−176.15 (12)	N2—N3—C12—C13	92.39 (14)
C2—C1—C6—C5	−1.3 (2)	C14—O4—C13—O3	−10.09 (19)
S1—C1—C6—C5	176.25 (10)	C14—O4—C13—C12	170.83 (11)
C2—C1—C6—C7	174.78 (13)	N3—C12—C13—O3	8.23 (18)
S1—C1—C6—C7	−7.70 (17)	N3—C12—C13—O4	−172.68 (10)
N3—N2—C7—C8	−0.47 (14)	C13—O4—C14—C16	155.92 (12)
N3—N2—C7—C6	177.38 (12)	C13—O4—C14—C15	−82.14 (14)
C5—C6—C7—N2	−19.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.95	2.54	3.4015 (17)	150
C12—H12A···N2ⁱⁱ	0.99	2.50	3.4413 (17)	158
C12—H12B···O1ⁱⁱⁱ	0.99	2.51	3.4694 (17)	163
C15—H15B···O3^iv	0.98	2.53	3.456 (2)	157

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₉N₃O₄S
M_r	349.40
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.6370 (2), 8.5412 (2), 13.3096 (4)
α, β, γ (°)	98.4584 (18), 97.4870 (13), 95.9599 (17)
V (Å³)	844.69 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.18 × 0.16 × 0.11

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.962, 0.977
No. of measured, independent and observed [I > 2.0σ(I)] reflections	12392, 3824, 3552
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.095, 1.04
No. of reflections	3824
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.38

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
C4—H4···O2ⁱ	0.95	2.54	3.4015 (17)	150
C12—H12A···N2ⁱⁱ	0.99	2.50	3.4413 (17)	158
C12—H12B···O1ⁱⁱⁱ	0.99	2.51	3.4694 (17)	163
C15—H15B···O3^iv	0.98	2.53	3.456 (2)	157

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

Acknowledgements

HLS is grateful to the Institute of Chemistry, University of the Punjab, Lahore, Pakistan, for financial support.

References

Ahmad, M., Siddiqui, H. L., Zia-ur-Rehman, M. & Parvez, M. (2010). Eur. J. Med. Chem. 45, 698–704. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 66| Part 10| October 2010| Page o2630

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

Isoprop­yl (3,4-di­methyl-5,5-dioxo-4H-pyrazolo­[4,3-c][1,2]benzo­thia­zin-2-yl)acetate

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Acknowledgements

References

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