Dimethyl 3-acetyl-3-(1,3-benzothia-zol-2-yl)penta-nedioate.

The title compound, C(16)H(17)NO(5)S, was one of two condensation products from the reaction of 1-(1,3-benzothia-zol-2-yl)propan-2-one with methyl chloro-acetate. The non-H atoms in each of the four substituent groups on the central quaternary C atom are virtually coplanar. The maximum deviations from the least-squares planes are 0.015 (2) and 0.020 (2) Å for the methyl C atoms in the methyl acetate substituents and 0.033 (1) Å for the linked C atom of the benzothia-zole substituent. The S, C and N atoms in the thia-zole ring of the benzothia-zole substituent lie -0.037 (2), 0.046 (2) and -0.028 (2) Å, respectively, from the mean plane defined by the benzene ring atoms.

Related literature

For general background, see: Palmer et al. (1971 ▶); Bénéteau et al., 1999 ▶; El-Sherbeny (2000 ▶); Abayeh et al. (1994 ▶); Ivanov & Yuritsyn (1971 ▶); Monsanto (1968 ▶); Lee et al. (2001 ▶). For related structures, see: Chen (1994 ▶); Chu et al. (2003 ▶).

Experimental

Crystal data

C16H17NO5S

M = 335.37

Monoclinic,

a = 14.4075 (3) Å

b = 8.8089 (2) Å

c = 13.8968 (3) Å

β = 118.011 (1)°

V = 1557.10 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 100 (2) K

0.54 × 0.47 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.883, T max = 0.945

94263 measured reflections

3766 independent reflections

3396 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.02

3766 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2004 ▶); 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: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808035782/fj2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035782/fj2155Isup2.hkl

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

C16H17NO5S	F000 = 704
Mr = 335.37	Dx = 1.431 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9633 reflections
a = 14.4075 (3) Å	θ = 2.8–32.7º
b = 8.8089 (2) Å	µ = 0.23 mm−1
c = 13.8968 (3) Å	T = 100 (2) K
β = 118.011 (1)º	Irregular, colourless
V = 1557.10 (6) Å3	0.54 × 0.47 × 0.25 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	3766 independent reflections
Radiation source: fine-focus sealed tube	3396 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.030
T = 100(2) K	θmax = 28.0º
φ and ω scans	θmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 2004)	h = −16→19
Tmin = 0.884, Tmax = 0.945	k = −11→11
94263 measured reflections	l = −18→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0379P)2 + 0.9909P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
3766 reflections	Δρmax = 0.40 e Å−3
211 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.07547 (2)	0.86573 (3)	0.43919 (2)	0.01676 (8)
C2	0.19378 (9)	0.80630 (13)	0.54977 (9)	0.0140 (2)
N3	0.20635 (8)	0.66132 (11)	0.56438 (8)	0.01443 (19)
C4	0.11159 (9)	0.42603 (14)	0.47444 (10)	0.0170 (2)
H4	0.1637	0.3622	0.5273	0.024 (2)*
C5	0.02392 (10)	0.36495 (14)	0.38745 (10)	0.0190 (2)
H5	0.0163	0.2578	0.3802	0.024 (2)*
C6	−0.05382 (10)	0.45859 (15)	0.30984 (10)	0.0193 (2)
H6	−0.1132	0.4135	0.2508	0.024 (2)*
C7	−0.04607 (9)	0.61526 (15)	0.31719 (9)	0.0179 (2)
H7	−0.0991	0.6784	0.2646	0.024 (2)*
C8	0.04263 (9)	0.67687 (14)	0.40475 (9)	0.0149 (2)
C9	0.12163 (9)	0.58417 (13)	0.48265 (9)	0.0141 (2)
C1	0.27346 (9)	0.92387 (13)	0.62176 (9)	0.0145 (2)
C10	0.22105 (9)	1.00619 (14)	0.68333 (9)	0.0160 (2)
O10	0.18549 (8)	1.13226 (10)	0.65710 (8)	0.0249 (2)
C11	0.20998 (10)	0.91849 (15)	0.77027 (10)	0.0219 (3)
H111	0.2794	0.9052	0.8335	0.0431 (14)*
H112	0.1792	0.8188	0.7417	0.0431 (14)*
H113	0.1641	0.9743	0.7922	0.0431 (14)*
C20	0.37450 (9)	0.84101 (13)	0.70162 (10)	0.0173 (2)
H201	0.3553	0.7532	0.7331	0.0431 (14)*
H202	0.4102	0.8014	0.6608	0.0431 (14)*
C21	0.45015 (9)	0.94072 (14)	0.79307 (10)	0.0170 (2)
O21	0.43873 (8)	1.07423 (11)	0.80278 (8)	0.0304 (2)
O22	0.53173 (7)	0.86031 (10)	0.86465 (8)	0.0229 (2)
C22	0.60859 (10)	0.94308 (15)	0.95845 (11)	0.0232 (3)
H221	0.6652	0.8742	1.0055	0.0431 (14)*
H222	0.5747	0.9852	0.9993	0.0431 (14)*
H223	0.6379	1.0258	0.9339	0.0431 (14)*
C30	0.29294 (10)	1.04297 (13)	0.55238 (10)	0.0168 (2)
H301	0.2280	1.1038	0.5129	0.0431 (14)*
H302	0.3489	1.1126	0.6021	0.0431 (14)*
C31	0.32428 (9)	0.98185 (14)	0.47030 (10)	0.0177 (2)
O31	0.34329 (8)	0.85225 (11)	0.45908 (8)	0.0272 (2)
O32	0.32806 (9)	1.09691 (11)	0.40907 (8)	0.0281 (2)
C32	0.36038 (13)	1.05932 (17)	0.32765 (12)	0.0309 (3)
H321	0.3587	1.1509	0.2869	0.0431 (14)*
H322	0.3123	0.9833	0.2774	0.0431 (14)*
H323	0.4320	1.0183	0.3636	0.0431 (14)*

	U11	U22	U33	U12	U13	U23
S1	0.01835 (15)	0.01332 (14)	0.01468 (14)	0.00202 (10)	0.00450 (11)	0.00100 (10)
C2	0.0143 (5)	0.0144 (5)	0.0137 (5)	0.0014 (4)	0.0071 (4)	0.0008 (4)
N3	0.0153 (4)	0.0135 (5)	0.0152 (5)	−0.0003 (4)	0.0078 (4)	−0.0001 (4)
C4	0.0197 (6)	0.0144 (5)	0.0205 (6)	0.0007 (4)	0.0124 (5)	0.0000 (4)
C5	0.0231 (6)	0.0159 (6)	0.0229 (6)	−0.0043 (5)	0.0150 (5)	−0.0047 (5)
C6	0.0201 (6)	0.0236 (6)	0.0165 (5)	−0.0058 (5)	0.0105 (5)	−0.0067 (5)
C7	0.0184 (5)	0.0222 (6)	0.0134 (5)	0.0001 (5)	0.0077 (5)	−0.0014 (4)
C8	0.0178 (5)	0.0144 (5)	0.0153 (5)	0.0001 (4)	0.0100 (5)	−0.0011 (4)
C9	0.0155 (5)	0.0150 (5)	0.0146 (5)	−0.0009 (4)	0.0094 (4)	−0.0010 (4)
C1	0.0161 (5)	0.0113 (5)	0.0160 (5)	0.0002 (4)	0.0074 (4)	0.0002 (4)
C10	0.0153 (5)	0.0164 (6)	0.0149 (5)	−0.0015 (4)	0.0059 (4)	−0.0022 (4)
O10	0.0319 (5)	0.0192 (5)	0.0284 (5)	0.0088 (4)	0.0181 (4)	0.0030 (4)
C11	0.0260 (6)	0.0235 (6)	0.0189 (6)	−0.0034 (5)	0.0127 (5)	−0.0007 (5)
C20	0.0157 (5)	0.0131 (5)	0.0193 (6)	0.0001 (4)	0.0050 (5)	−0.0006 (4)
C21	0.0146 (5)	0.0172 (6)	0.0189 (6)	−0.0013 (4)	0.0077 (5)	−0.0003 (4)
O21	0.0262 (5)	0.0173 (5)	0.0323 (5)	0.0016 (4)	0.0011 (4)	−0.0066 (4)
O22	0.0195 (4)	0.0179 (4)	0.0214 (4)	−0.0004 (3)	0.0013 (4)	−0.0009 (4)
C22	0.0160 (5)	0.0240 (6)	0.0220 (6)	−0.0038 (5)	0.0026 (5)	−0.0027 (5)
C30	0.0211 (6)	0.0121 (5)	0.0191 (6)	−0.0011 (4)	0.0110 (5)	−0.0004 (4)
C31	0.0172 (5)	0.0173 (6)	0.0187 (6)	−0.0036 (4)	0.0086 (5)	−0.0019 (5)
O31	0.0409 (6)	0.0178 (5)	0.0324 (5)	0.0027 (4)	0.0250 (5)	−0.0007 (4)
O32	0.0501 (6)	0.0179 (5)	0.0291 (5)	−0.0045 (4)	0.0290 (5)	−0.0020 (4)
C32	0.0486 (9)	0.0270 (7)	0.0308 (7)	−0.0086 (6)	0.0300 (7)	−0.0046 (6)

S1—C8	1.7343 (12)	C11—H112	0.9800
S1—C2	1.7552 (12)	C11—H113	0.9800
C2—N3	1.2924 (15)	C20—C21	1.5078 (16)
C2—C1	1.5207 (16)	C20—H201	0.9900
N3—C9	1.3926 (15)	C20—H202	0.9900
C4—C5	1.3827 (18)	C21—O21	1.2038 (16)
C4—C9	1.3997 (16)	C21—O22	1.3320 (15)
C4—H4	0.9500	O22—C22	1.4496 (15)
C5—C6	1.4012 (18)	C22—H221	0.9800
C5—H5	0.9500	C22—H222	0.9800
C6—C7	1.3845 (18)	C22—H223	0.9800
C6—H6	0.9500	C30—C31	1.5095 (16)
C7—C8	1.3957 (17)	C30—H301	0.9900
C7—H7	0.9500	C30—H302	0.9900
C8—C9	1.4060 (16)	C31—O31	1.2012 (15)
C1—C30	1.5373 (16)	C31—O32	1.3409 (15)
C1—C20	1.5383 (16)	O32—C32	1.4497 (16)
C1—C10	1.5605 (16)	C32—H321	0.9800
C10—O10	1.2055 (15)	C32—H322	0.9800
C10—C11	1.5043 (17)	C32—H323	0.9800
C11—H111	0.9800
C8—S1—C2	88.99 (6)	C10—C11—H113	109.5
N3—C2—C1	124.25 (10)	H111—C11—H113	109.5
N3—C2—S1	116.04 (9)	H112—C11—H113	109.5
C1—C2—S1	119.70 (8)	C21—C20—C1	113.34 (10)
C2—N3—C9	110.46 (10)	C21—C20—H201	108.9
C5—C4—C9	118.40 (11)	C1—C20—H201	108.9
C5—C4—H4	120.8	C21—C20—H202	108.9
C9—C4—H4	120.8	C1—C20—H202	108.9
C4—C5—C6	121.04 (11)	H201—C20—H202	107.7
C4—C5—H5	119.5	O21—C21—O22	123.70 (11)
C6—C5—H5	119.5	O21—C21—C20	125.51 (11)
C7—C6—C5	121.49 (11)	O22—C21—C20	110.77 (10)
C7—C6—H6	119.3	C21—O22—C22	115.95 (10)
C5—C6—H6	119.3	O22—C22—H221	109.5
C6—C7—C8	117.45 (11)	O22—C22—H222	109.5
C6—C7—H7	121.3	H221—C22—H222	109.5
C8—C7—H7	121.3	O22—C22—H223	109.5
C7—C8—C9	121.61 (11)	H221—C22—H223	109.5
C7—C8—S1	129.28 (10)	H222—C22—H223	109.5
C9—C8—S1	109.11 (9)	C31—C30—C1	115.97 (10)
N3—C9—C4	124.73 (11)	C31—C30—H301	108.3
N3—C9—C8	115.28 (10)	C1—C30—H301	108.3
C4—C9—C8	120.00 (11)	C31—C30—H302	108.3
C2—C1—C30	110.85 (9)	C1—C30—H302	108.3
C2—C1—C20	108.53 (9)	H301—C30—H302	107.4
C30—C1—C20	112.75 (10)	O31—C31—O32	123.80 (11)
C2—C1—C10	105.49 (9)	O31—C31—C30	127.20 (11)
C30—C1—C10	107.74 (9)	O32—C31—C30	109.00 (10)
C20—C1—C10	111.26 (9)	C31—O32—C32	116.51 (11)
O10—C10—C11	121.71 (11)	O32—C32—H321	109.5
O10—C10—C1	120.57 (11)	O32—C32—H322	109.5
C11—C10—C1	117.58 (10)	H321—C32—H322	109.5
C10—C11—H111	109.5	O32—C32—H323	109.5
C10—C11—H112	109.5	H321—C32—H323	109.5
H111—C11—H112	109.5	H322—C32—H323	109.5
C8—S1—C2—N3	−3.31 (9)	N3—C2—C1—C10	−111.43 (12)
C8—S1—C2—C1	177.11 (9)	S1—C2—C1—C10	68.12 (11)
C1—C2—N3—C9	−177.68 (10)	C2—C1—C10—O10	−104.69 (13)
S1—C2—N3—C9	2.75 (12)	C30—C1—C10—O10	13.77 (15)
C9—C4—C5—C6	−0.72 (17)	C20—C1—C10—O10	137.83 (12)
C4—C5—C6—C7	−0.08 (18)	C2—C1—C10—C11	71.08 (12)
C5—C6—C7—C8	0.34 (17)	C30—C1—C10—C11	−170.47 (10)
C6—C7—C8—C9	0.21 (17)	C20—C1—C10—C11	−46.41 (14)
C6—C7—C8—S1	−178.77 (9)	C2—C1—C20—C21	−167.17 (9)
C2—S1—C8—C7	−178.22 (11)	C30—C1—C20—C21	69.63 (13)
C2—S1—C8—C9	2.70 (8)	C10—C1—C20—C21	−51.54 (13)
C2—N3—C9—C4	179.46 (11)	C1—C20—C21—O21	−3.89 (18)
C2—N3—C9—C8	−0.50 (14)	C1—C20—C21—O22	174.63 (10)
C5—C4—C9—N3	−178.70 (10)	O21—C21—O22—C22	0.40 (18)
C5—C4—C9—C8	1.25 (17)	C20—C21—O22—C22	−178.16 (10)
C7—C8—C9—N3	178.94 (10)	C2—C1—C30—C31	−53.93 (13)
S1—C8—C9—N3	−1.90 (12)	C20—C1—C30—C31	67.97 (13)
C7—C8—C9—C4	−1.02 (17)	C10—C1—C30—C31	−168.88 (10)
S1—C8—C9—C4	178.15 (9)	C1—C30—C31—O31	−6.12 (19)
N3—C2—C1—C30	132.23 (12)	C1—C30—C31—O32	173.84 (10)
S1—C2—C1—C30	−48.22 (12)	O31—C31—O32—C32	−1.96 (19)
N3—C2—C1—C20	7.89 (15)	C30—C31—O32—C32	178.08 (11)
S1—C2—C1—C20	−172.56 (8)