2-Chloro-ethyl 2-(2-chloro-phen-yl)-2-(4,5,6,7-tetrahydro-thieno[3,2-c]pyridin-5-yl)acetate.

The mol-ecular packing of the title compound, C(17)H(17)Cl(2)NO(2)S, is stabilized by weak C-H⋯O and C-H⋯Cl inter-actions. The ester chain is almost planar with a mean deviation of 0.0605 Å and makes dihedral angles of 71.60 (4) and 74.70 (8)° with the benzene ring and the thio-phene ring, respectively. The benzene and thio-phene rings make a dihedral angle of 84.22 (7)°.

Related literature

The title compound is a derivative of clopidogrel. For background to the bioactivity and applications of the anti­platelet agent clopidogrel, see, for example, Gurbel & Tantry (2007 ▶); Muller et al. (2003 ▶); Savi et al. (1994 ▶); Sharis et al. (1998 ▶). For the synthesis of other derivatives with thienopyridine, see: Aubert et al. (1985 ▶); Bipin et al. (2002 ▶); Bouisset & Radisson (1991 ▶).

Experimental

Crystal data

C17H17Cl2NO2S

M = 370.28

Monoclinic,

a = 9.689 (1) Å

b = 11.2670 (12) Å

c = 15.5670 (16) Å

β = 100.509 (8)°

V = 1670.9 (3) Å3

Z = 4

Cu Kα radiation

μ = 4.73 mm−1

T = 113 K

0.26 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.373, T max = 0.451

18109 measured reflections

3203 independent reflections

2974 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.09

3203 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.50 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046908/fk2029sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046908/fk2029Isup2.hkl

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

C17H17Cl2NO2S	F(000) = 768
Mr = 370.28	Dx = 1.472 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 2162 reflections
a = 9.689 (1) Å	θ = 27.6–72.0°
b = 11.2670 (12) Å	µ = 4.73 mm−1
c = 15.5670 (16) Å	T = 113 K
β = 100.509 (8)°	Prism, colorless
V = 1670.9 (3) Å3	0.26 × 0.24 × 0.20 mm
Z = 4

Rigaku Saturn diffractometer	3203 independent reflections
Radiation source: fine-focus sealed tube	2974 reflections with I > 2σ(I)
multilayer	Rint = 0.065
Detector resolution: 14.63 pixels mm-1	θmax = 72.6°, θmin = 4.9°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −13→13
Tmin = 0.373, Tmax = 0.451	l = −19→15
18109 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.6161P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
3203 reflections	Δρmax = 0.55 e Å−3
210 parameters	Δρmin = −0.50 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0023 (4)

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
Cl1	0.04822 (5)	0.57741 (4)	0.11386 (3)	0.02277 (16)
Cl2	0.76621 (5)	0.81053 (4)	0.43330 (3)	0.02378 (16)
S1	−0.27359 (5)	0.25362 (4)	0.37037 (3)	0.02083 (16)
O1	0.32239 (15)	0.54792 (13)	0.45403 (9)	0.0225 (3)
O2	0.39640 (14)	0.66198 (12)	0.35279 (9)	0.0174 (3)
N1	0.08010 (16)	0.47629 (13)	0.32205 (10)	0.0130 (3)
C1	−0.1656 (2)	0.13256 (17)	0.36824 (13)	0.0210 (4)
H1	−0.1959	0.0524	0.3685	0.025*
C2	−0.0317 (2)	0.16624 (17)	0.36612 (13)	0.0179 (4)
H2	0.0432	0.1120	0.3656	0.022*
C3	−0.01587 (19)	0.29199 (16)	0.36478 (12)	0.0144 (4)
C4	−0.13725 (19)	0.35097 (16)	0.36683 (12)	0.0153 (4)
C5	−0.1531 (2)	0.48332 (16)	0.36218 (13)	0.0176 (4)
H5A	−0.2034	0.5113	0.4083	0.021*
H5B	−0.2085	0.5066	0.3048	0.021*
C6	−0.0070 (2)	0.53980 (16)	0.37471 (13)	0.0169 (4)
H6A	−0.0154	0.6242	0.3568	0.020*
H6B	0.0376	0.5364	0.4372	0.020*
C7	0.11670 (19)	0.35649 (16)	0.35549 (14)	0.0175 (4)
H7A	0.1803	0.3613	0.4129	0.021*
H7B	0.1657	0.3130	0.3146	0.021*
C8	0.19666 (18)	0.54645 (15)	0.30224 (12)	0.0139 (4)
H8	0.1549	0.6221	0.2756	0.017*
C9	0.26203 (18)	0.48536 (15)	0.23238 (12)	0.0132 (4)
C10	0.19866 (18)	0.49132 (16)	0.14532 (12)	0.0143 (4)
C11	0.2530 (2)	0.43267 (17)	0.08043 (13)	0.0175 (4)
H11	0.2070	0.4375	0.0212	0.021*
C12	0.3751 (2)	0.36703 (16)	0.10307 (13)	0.0179 (4)
H12	0.4127	0.3261	0.0592	0.021*
C13	0.44201 (19)	0.36086 (16)	0.18876 (13)	0.0164 (4)
H13	0.5268	0.3171	0.2039	0.020*
C14	0.38540 (19)	0.41882 (15)	0.25317 (13)	0.0155 (4)
H14	0.4314	0.4131	0.3124	0.019*
C15	0.31009 (19)	0.58238 (15)	0.37984 (13)	0.0160 (4)
C16	0.5174 (2)	0.69884 (17)	0.41623 (13)	0.0188 (4)
H16A	0.5675	0.6293	0.4458	0.023*
H16B	0.4892	0.7517	0.4608	0.023*
C17	0.6085 (2)	0.76441 (17)	0.36247 (14)	0.0202 (4)
H17A	0.5577	0.8345	0.3342	0.024*
H17B	0.6316	0.7118	0.3162	0.024*

	U11	U22	U33	U12	U13	U23
Cl1	0.0140 (2)	0.0368 (3)	0.0168 (3)	0.00997 (17)	0.00123 (19)	0.00264 (18)
Cl2	0.0144 (3)	0.0303 (3)	0.0259 (3)	−0.00757 (16)	0.0018 (2)	0.00000 (18)
S1	0.0121 (3)	0.0269 (3)	0.0237 (3)	−0.00480 (16)	0.0040 (2)	0.00486 (18)
O1	0.0192 (7)	0.0317 (7)	0.0173 (8)	−0.0060 (6)	0.0050 (6)	0.0020 (6)
O2	0.0138 (6)	0.0248 (7)	0.0131 (7)	−0.0073 (5)	0.0014 (5)	0.0002 (5)
N1	0.0113 (7)	0.0173 (7)	0.0119 (8)	−0.0005 (6)	0.0062 (6)	0.0000 (6)
C1	0.0235 (10)	0.0211 (9)	0.0194 (11)	−0.0054 (7)	0.0063 (8)	0.0003 (7)
C2	0.0217 (10)	0.0208 (9)	0.0126 (10)	−0.0013 (7)	0.0065 (8)	0.0001 (7)
C3	0.0136 (9)	0.0210 (9)	0.0090 (9)	−0.0004 (7)	0.0033 (7)	0.0018 (7)
C4	0.0141 (9)	0.0241 (9)	0.0079 (9)	−0.0021 (7)	0.0027 (7)	0.0012 (7)
C5	0.0148 (9)	0.0225 (9)	0.0174 (10)	0.0024 (7)	0.0077 (8)	0.0037 (7)
C6	0.0154 (9)	0.0186 (8)	0.0191 (10)	0.0005 (7)	0.0100 (8)	−0.0004 (7)
C7	0.0101 (8)	0.0171 (8)	0.0262 (11)	0.0005 (6)	0.0058 (8)	0.0031 (7)
C8	0.0111 (8)	0.0172 (8)	0.0143 (9)	−0.0011 (6)	0.0049 (7)	−0.0002 (7)
C9	0.0093 (8)	0.0167 (8)	0.0143 (9)	−0.0025 (6)	0.0044 (7)	0.0013 (6)
C10	0.0103 (8)	0.0205 (8)	0.0123 (10)	−0.0005 (6)	0.0026 (7)	0.0007 (7)
C11	0.0135 (9)	0.0243 (9)	0.0145 (10)	−0.0015 (7)	0.0020 (7)	−0.0003 (7)
C12	0.0169 (9)	0.0207 (9)	0.0174 (10)	0.0008 (7)	0.0068 (8)	−0.0030 (7)
C13	0.0131 (9)	0.0204 (9)	0.0161 (10)	0.0024 (7)	0.0036 (7)	0.0001 (7)
C14	0.0114 (9)	0.0190 (9)	0.0159 (10)	−0.0006 (6)	0.0023 (7)	0.0013 (7)
C15	0.0124 (9)	0.0183 (9)	0.0188 (11)	−0.0002 (6)	0.0068 (8)	−0.0017 (7)
C16	0.0137 (9)	0.0262 (10)	0.0162 (10)	−0.0057 (7)	0.0024 (8)	−0.0035 (7)
C17	0.0140 (9)	0.0240 (9)	0.0222 (11)	−0.0049 (7)	0.0022 (8)	−0.0004 (8)

Cl1—C10	1.7450 (18)	C6—H6B	0.9900
Cl2—C17	1.791 (2)	C7—H7A	0.9900
S1—C1	1.723 (2)	C7—H7B	0.9900
S1—C4	1.7256 (18)	C8—C9	1.520 (2)
O1—C15	1.204 (2)	C8—C15	1.532 (3)
O2—C15	1.345 (2)	C8—H8	1.0000
O2—C16	1.449 (2)	C9—C10	1.384 (3)
N1—C8	1.457 (2)	C9—C14	1.398 (3)
N1—C6	1.466 (2)	C10—C11	1.389 (3)
N1—C7	1.467 (2)	C11—C12	1.385 (3)
C1—C2	1.358 (3)	C11—H11	0.9500
C1—H1	0.9500	C12—C13	1.374 (3)
C2—C3	1.426 (3)	C12—H12	0.9500
C2—H2	0.9500	C13—C14	1.390 (3)
C3—C4	1.356 (3)	C13—H13	0.9500
C3—C7	1.506 (2)	C14—H14	0.9500
C4—C5	1.499 (3)	C16—C17	1.515 (3)
C5—C6	1.532 (3)	C16—H16A	0.9900
C5—H5A	0.9900	C16—H16B	0.9900
C5—H5B	0.9900	C17—H17A	0.9900
C6—H6A	0.9900	C17—H17B	0.9900
C1—S1—C4	91.80 (9)	C9—C8—C15	110.57 (14)
C15—O2—C16	116.73 (15)	N1—C8—H8	106.2
C8—N1—C6	113.66 (14)	C9—C8—H8	106.2
C8—N1—C7	115.33 (14)	C15—C8—H8	106.2
C6—N1—C7	112.16 (14)	C10—C9—C14	117.43 (17)
C2—C1—S1	111.44 (15)	C10—C9—C8	120.70 (16)
C2—C1—H1	124.3	C14—C9—C8	121.85 (17)
S1—C1—H1	124.3	C9—C10—C11	122.00 (17)
C1—C2—C3	112.55 (17)	C9—C10—Cl1	120.04 (14)
C1—C2—H2	123.7	C11—C10—Cl1	117.94 (15)
C3—C2—H2	123.7	C12—C11—C10	119.25 (19)
C4—C3—C2	113.01 (17)	C12—C11—H11	120.4
C4—C3—C7	121.62 (16)	C10—C11—H11	120.4
C2—C3—C7	125.23 (16)	C13—C12—C11	120.25 (18)
C3—C4—C5	124.61 (16)	C13—C12—H12	119.9
C3—C4—S1	111.19 (14)	C11—C12—H12	119.9
C5—C4—S1	124.14 (14)	C12—C13—C14	119.86 (17)
C4—C5—C6	108.82 (15)	C12—C13—H13	120.1
C4—C5—H5A	109.9	C14—C13—H13	120.1
C6—C5—H5A	109.9	C13—C14—C9	121.20 (18)
C4—C5—H5B	109.9	C13—C14—H14	119.4
C6—C5—H5B	109.9	C9—C14—H14	119.4
H5A—C5—H5B	108.3	O1—C15—O2	123.85 (18)
N1—C6—C5	109.83 (15)	O1—C15—C8	127.06 (17)
N1—C6—H6A	109.7	O2—C15—C8	109.08 (15)
C5—C6—H6A	109.7	O2—C16—C17	104.11 (16)
N1—C6—H6B	109.7	O2—C16—H16A	110.9
C5—C6—H6B	109.7	C17—C16—H16A	110.9
H6A—C6—H6B	108.2	O2—C16—H16B	110.9
N1—C7—C3	108.85 (15)	C17—C16—H16B	110.9
N1—C7—H7A	109.9	H16A—C16—H16B	109.0
C3—C7—H7A	109.9	C16—C17—Cl2	108.60 (15)
N1—C7—H7B	109.9	C16—C17—H17A	110.0
C3—C7—H7B	109.9	Cl2—C17—H17A	110.0
H7A—C7—H7B	108.3	C16—C17—H17B	110.0
N1—C8—C9	110.25 (14)	Cl2—C17—H17B	110.0
N1—C8—C15	116.67 (15)	H17A—C17—H17B	108.4
C4—S1—C1—C2	0.79 (17)	N1—C8—C9—C10	78.1 (2)
S1—C1—C2—C3	−0.9 (2)	C15—C8—C9—C10	−151.36 (16)
C1—C2—C3—C4	0.6 (2)	N1—C8—C9—C14	−100.15 (19)
C1—C2—C3—C7	−175.08 (19)	C15—C8—C9—C14	30.3 (2)
C2—C3—C4—C5	−177.23 (17)	C14—C9—C10—C11	0.9 (3)
C7—C3—C4—C5	−1.3 (3)	C8—C9—C10—C11	−177.49 (16)
C2—C3—C4—S1	0.0 (2)	C14—C9—C10—Cl1	−177.49 (13)
C7—C3—C4—S1	175.86 (15)	C8—C9—C10—Cl1	4.1 (2)
C1—S1—C4—C3	−0.42 (16)	C9—C10—C11—C12	−0.6 (3)
C1—S1—C4—C5	176.78 (17)	Cl1—C10—C11—C12	177.76 (14)
C3—C4—C5—C6	−12.0 (3)	C10—C11—C12—C13	−0.5 (3)
S1—C4—C5—C6	171.12 (14)	C11—C12—C13—C14	1.3 (3)
C8—N1—C6—C5	157.57 (15)	C12—C13—C14—C9	−1.0 (3)
C7—N1—C6—C5	−69.4 (2)	C10—C9—C14—C13	0.0 (3)
C4—C5—C6—N1	44.8 (2)	C8—C9—C14—C13	178.30 (16)
C8—N1—C7—C3	−174.85 (15)	C16—O2—C15—O1	5.7 (3)
C6—N1—C7—C3	52.9 (2)	C16—O2—C15—C8	−175.09 (14)
C4—C3—C7—N1	−18.0 (3)	N1—C8—C15—O1	9.3 (3)
C2—C3—C7—N1	157.41 (17)	C9—C8—C15—O1	−117.7 (2)
C6—N1—C8—C9	−167.86 (15)	N1—C8—C15—O2	−169.92 (14)
C7—N1—C8—C9	60.6 (2)	C9—C8—C15—O2	63.05 (18)
C6—N1—C8—C15	65.0 (2)	C15—O2—C16—C17	167.79 (15)
C7—N1—C8—C15	−66.6 (2)	O2—C16—C17—Cl2	−177.94 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7a···O1	0.99	2.53	3.140 (2)	120.0
C8—H8···Cl1	1.00	2.59	3.042 (2)	107

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7a⋯O1	0.99	2.53	3.140 (2)	120
C8—H8⋯Cl1	1.00	2.59	3.042 (2)	107