Literature DB >> 21579092

Methyl 2-(1,1,3-trioxo-2,3-dihydro-1,2-benzothia-zol-2-yl)acetate: a monoclinic polymorph.

Muhammad Zia-Ur-Rehman, Muhammad Nadeem Arshad, Shafaq Mubarak, Islam Ullah Khan.

Abstract

In the title compound, C(10)H(9)NO(5)S, the fused ring system and the planar (r.m.s. deviation = 0.0037 Å) methoxy-carbonyl-methyl side chain form a dihedral angle of 84.67 (10)°. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds. A triclinic polymorph of the title compound is already known [Siddiqui et al. (2008 ▶). Acta Cryst. E64, o859].

Entities: Chemical Disease Gene

Year: 2010 PMID： 21579092 PMCID： PMC2979295 DOI： 10.1107/S1600536810012006

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For the synthesis and biological activity of related compounds, see: Ahmad et al. (2010 ▶); Zia-ur-Rehman et al. (2005 ▶, 2006 ▶, 2007 ▶). For a related structure, see: Arshad et al. (2009 ▶). For the triclinic polymorph, see: Siddiqui et al. (2008 ▶).

Experimental

Crystal data

C10H9NO5S M = 255.24 Monoclinic, a = 8.9418 (4) Å b = 12.7595 (6) Å c = 10.3145 (5) Å β = 107.300 (1)° V = 1123.57 (9) Å3 Z = 4 Mo Kα radiation μ = 0.30 mm−1 T = 296 K 0.43 × 0.41 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.883, T max = 0.962 12621 measured reflections 2796 independent reflections 2022 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.115 S = 1.03 2796 reflections 155 parameters H-atom parameters constrained Δρmax = 0.24 e Å−3 Δρmin = −0.32 e Å−3 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012006/bt5235sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012006/bt5235Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₀H₉NO₅S	F(000) = 528
M_r = 255.24	D_x = 1.509 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4707 reflections
a = 8.9418 (4) Å	θ = 2.7–26.7°
b = 12.7595 (6) Å	µ = 0.30 mm⁻¹
c = 10.3145 (5) Å	T = 296 K
β = 107.300 (1)°	Needles, colourless
V = 1123.57 (9) Å³	0.43 × 0.41 × 0.13 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2796 independent reflections
Radiation source: fine-focus sealed tube	2022 reflections with I > 2σ(I)
graphite	R_int = 0.025
phi and ω scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
T_min = 0.883, T_max = 0.962	k = −16→17
12621 measured reflections	l = −13→12

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) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0523P)² + 0.2836P] where P = (F_o² + 2F_c²)/3
2796 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	U_iso*/U_eq
S1	0.38220 (5)	0.08616 (4)	0.63435 (4)	0.05841 (18)
O1	0.16399 (18)	0.16167 (11)	0.27984 (13)	0.0700 (4)
O2	0.33381 (18)	0.13244 (13)	0.74048 (13)	0.0744 (4)
O3	0.54303 (16)	0.05974 (16)	0.66339 (16)	0.0892 (5)
O4	0.17124 (19)	0.34008 (12)	0.54605 (16)	0.0776 (4)
O5	0.33001 (19)	0.44091 (12)	0.46863 (15)	0.0729 (4)
N1	0.3269 (2)	0.16078 (13)	0.49608 (15)	0.0602 (4)
C1	0.25915 (19)	−0.01610 (14)	0.55496 (17)	0.0491 (4)
C2	0.2399 (3)	−0.11272 (17)	0.6095 (2)	0.0649 (5)
H2	0.2951	−0.1303	0.6984	0.078*
C3	0.1358 (3)	−0.18129 (17)	0.5268 (2)	0.0720 (6)
H3	0.1196	−0.2466	0.5605	0.086*
C4	0.0549 (3)	−0.15539 (16)	0.3951 (2)	0.0681 (6)
H4	−0.0144	−0.2036	0.3413	0.082*
C5	0.0746 (2)	−0.05929 (15)	0.3415 (2)	0.0556 (4)
H5	0.0201	−0.0423	0.2523	0.067*
C6	0.17697 (18)	0.01082 (13)	0.42324 (16)	0.0449 (4)
C7	0.2156 (2)	0.11722 (15)	0.38655 (17)	0.0508 (4)
C8	0.3914 (3)	0.26501 (17)	0.4912 (2)	0.0697 (6)
H8A	0.4143	0.2735	0.4056	0.084*
H8B	0.4892	0.2714	0.5636	0.084*
C9	0.2822 (2)	0.35100 (16)	0.50537 (18)	0.0603 (5)
C10	0.2369 (3)	0.53266 (18)	0.4757 (2)	0.0805 (7)
H10A	0.1314	0.5223	0.4189	0.121*
H10B	0.2809	0.5930	0.4450	0.121*
H10C	0.2368	0.5433	0.5678	0.121*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0530 (3)	0.0830 (4)	0.0369 (2)	0.0002 (2)	0.00972 (18)	−0.0025 (2)
O1	0.0958 (11)	0.0643 (9)	0.0439 (7)	0.0047 (7)	0.0117 (7)	0.0109 (6)
O2	0.0837 (10)	0.0975 (11)	0.0418 (7)	−0.0028 (8)	0.0183 (7)	−0.0136 (7)
O3	0.0478 (8)	0.1463 (16)	0.0655 (10)	0.0058 (9)	0.0046 (7)	−0.0070 (10)
O4	0.0842 (10)	0.0759 (10)	0.0847 (11)	−0.0175 (8)	0.0436 (9)	0.0019 (8)
O5	0.0924 (11)	0.0655 (9)	0.0701 (9)	−0.0261 (8)	0.0383 (8)	−0.0062 (7)
N1	0.0750 (10)	0.0620 (10)	0.0416 (8)	−0.0159 (8)	0.0140 (7)	−0.0033 (7)
C1	0.0490 (9)	0.0595 (10)	0.0414 (8)	0.0098 (8)	0.0176 (7)	0.0036 (7)
C2	0.0748 (13)	0.0683 (13)	0.0589 (12)	0.0215 (10)	0.0312 (10)	0.0200 (10)
C3	0.0869 (15)	0.0536 (12)	0.0892 (16)	0.0044 (11)	0.0471 (13)	0.0101 (11)
C4	0.0695 (13)	0.0585 (12)	0.0837 (15)	−0.0092 (10)	0.0340 (11)	−0.0112 (11)
C5	0.0519 (10)	0.0594 (11)	0.0543 (10)	0.0007 (8)	0.0139 (8)	−0.0039 (8)
C6	0.0437 (8)	0.0503 (9)	0.0416 (8)	0.0061 (7)	0.0140 (7)	0.0016 (7)
C7	0.0589 (10)	0.0548 (10)	0.0387 (9)	0.0022 (8)	0.0146 (8)	−0.0011 (7)
C8	0.0799 (14)	0.0725 (14)	0.0637 (12)	−0.0248 (11)	0.0319 (11)	−0.0117 (10)
C9	0.0734 (13)	0.0662 (12)	0.0434 (10)	−0.0248 (10)	0.0203 (9)	−0.0088 (8)
C10	0.1110 (19)	0.0673 (14)	0.0676 (14)	−0.0142 (13)	0.0335 (13)	−0.0033 (11)

S1—O3	1.4196 (15)	C3—C4	1.376 (3)
S1—O2	1.4199 (14)	C3—H3	0.9300
S1—N1	1.6630 (16)	C4—C5	1.378 (3)
S1—C1	1.7457 (19)	C4—H4	0.9300
O1—C7	1.202 (2)	C5—C6	1.375 (2)
O4—C9	1.194 (2)	C5—H5	0.9300
O5—C9	1.319 (2)	C6—C7	1.478 (3)
O5—C10	1.451 (3)	C8—C9	1.505 (3)
N1—C7	1.381 (2)	C8—H8A	0.9700
N1—C8	1.456 (3)	C8—H8B	0.9700
C1—C6	1.382 (2)	C10—H10A	0.9600
C1—C2	1.387 (3)	C10—H10B	0.9600
C2—C3	1.374 (3)	C10—H10C	0.9600
C2—H2	0.9300

O3—S1—O2	117.25 (9)	C6—C5—H5	120.8
O3—S1—N1	109.94 (10)	C4—C5—H5	120.8
O2—S1—N1	110.00 (10)	C5—C6—C1	120.23 (17)
O3—S1—C1	112.28 (10)	C5—C6—C7	127.21 (16)
O2—S1—C1	112.24 (9)	C1—C6—C7	112.55 (15)
N1—S1—C1	92.32 (8)	O1—C7—N1	123.13 (17)
C9—O5—C10	116.58 (17)	O1—C7—C6	127.78 (17)
C7—N1—C8	122.39 (16)	N1—C7—C6	109.08 (15)
C7—N1—S1	115.42 (13)	N1—C8—C9	112.79 (16)
C8—N1—S1	122.19 (14)	N1—C8—H8A	109.0
C6—C1—C2	121.73 (18)	C9—C8—H8A	109.0
C6—C1—S1	110.62 (13)	N1—C8—H8B	109.0
C2—C1—S1	127.65 (15)	C9—C8—H8B	109.0
C3—C2—C1	117.17 (19)	H8A—C8—H8B	107.8
C3—C2—H2	121.4	O4—C9—O5	125.2 (2)
C1—C2—H2	121.4	O4—C9—C8	125.44 (19)
C2—C3—C4	121.4 (2)	O5—C9—C8	109.32 (17)
C2—C3—H3	119.3	O5—C10—H10A	109.5
C4—C3—H3	119.3	O5—C10—H10B	109.5
C3—C4—C5	121.2 (2)	H10A—C10—H10B	109.5
C3—C4—H4	119.4	O5—C10—H10C	109.5
C5—C4—H4	119.4	H10A—C10—H10C	109.5
C6—C5—C4	118.33 (19)	H10B—C10—H10C	109.5

O3—S1—N1—C7	115.77 (16)	C2—C1—C6—C5	−1.0 (3)
O2—S1—N1—C7	−113.66 (15)	S1—C1—C6—C5	179.06 (13)
C1—S1—N1—C7	1.03 (15)	C2—C1—C6—C7	179.97 (16)
O3—S1—N1—C8	−64.37 (18)	S1—C1—C6—C7	0.06 (18)
O2—S1—N1—C8	66.20 (18)	C8—N1—C7—O1	0.0 (3)
C1—S1—N1—C8	−179.10 (16)	S1—N1—C7—O1	179.84 (15)
O3—S1—C1—C6	−113.27 (13)	C8—N1—C7—C6	179.00 (16)
O2—S1—C1—C6	112.14 (13)	S1—N1—C7—C6	−1.14 (19)
N1—S1—C1—C6	−0.60 (13)	C5—C6—C7—O1	0.7 (3)
O3—S1—C1—C2	66.84 (19)	C1—C6—C7—O1	179.61 (18)
O2—S1—C1—C2	−67.76 (18)	C5—C6—C7—N1	−178.26 (17)
N1—S1—C1—C2	179.51 (17)	C1—C6—C7—N1	0.6 (2)
C6—C1—C2—C3	0.3 (3)	C7—N1—C8—C9	77.7 (2)
S1—C1—C2—C3	−179.82 (14)	S1—N1—C8—C9	−102.1 (2)
C1—C2—C3—C4	0.4 (3)	C10—O5—C9—O4	−1.6 (3)
C2—C3—C4—C5	−0.4 (3)	C10—O5—C9—C8	179.77 (17)
C3—C4—C5—C6	−0.4 (3)	N1—C8—C9—O4	16.0 (3)
C4—C5—C6—C1	1.0 (3)	N1—C8—C9—O5	−165.36 (16)
C4—C5—C6—C7	179.88 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.97	2.46	3.371 (3)	156
C2—H2···O4ⁱⁱ	0.93	2.59	3.455 (3)	155
C3—H3···O2ⁱⁱ	0.93	2.50	3.331 (3)	148
C10—H10C···O2ⁱⁱⁱ	0.96	2.52	3.419 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1ⁱ	0.97	2.46	3.371 (3)	156
C2—H2⋯O4ⁱⁱ	0.93	2.59	3.455 (3)	155
C3—H3⋯O2ⁱⁱ	0.93	2.50	3.331 (3)	148
C10—H10C⋯O2ⁱⁱⁱ	0.96	2.52	3.419 (3)	156

Symmetry codes: (i) ; (ii) ; (iii) .

6 in total

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Authors: Muhammad Zia-ur-Rehman; Jamil Anwar Choudary; Saeed Ahmad; Hamid Latif Siddiqui
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