Ethyl 4-[(4-chloro­phen­oxy)meth­yl]-2-(4-nitro­phen­yl)-1,3-thia­zole-5-carboxyl­ate

Deng, Z.-R.; Wang, S.-Q.; Dong, W.-L.; Wang, R.-L.

doi:10.1107/S1600536811049774

organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page o3433

https://doi.org/10.1107/S1600536811049774

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Ethyl 4-[(4-chlorophenoxy)methyl]-2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate

Zhi-Rong Deng,^a Shu-Qing Wang,^a Wei-Li Dong ^a ^* and Run-Ling Wang ^a ^*

^aTianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, Tianjin 300070, People's Republic of China
^*Correspondence e-mail: dwllilly@163.com,

(Received 15 November 2011; accepted 21 November 2011; online 25 November 2011)

The title compound, C₁₉H₁₅ClN₂O₅S, contains two molecules (A and B) in the asymmetric unit. In molecule A, the dihedral angles between the thiazole ring and the pendant chlorobenzene and nitrobenzene rings are 72.14 (15) and 3.03 (15)°, respectively. The corresponding angles for molecule B are 45.56 (16) and 1.51 (14)°, respectively. In the crystal, both molecules form inversion dimers linked by pairs of weak C—H⋯O interactions.

Related literature

For the biological activity of related compounds and for related structures, see: Liu et al. (2011a ,b ,c ,d ). For further synthetic details, see: Cho et al. (2010 ).

Experimental

Crystal data

C₁₉H₁₅ClN₂O₅S
M_r = 418.84
Triclinic, $[P \overline 1]$
a = 7.658 (2) Å
b = 7.736 (2) Å
c = 31.462 (9) Å
α = 95.414 (8)°
β = 93.595 (13)°
γ = 95.536 (9)°
V = 1841.9 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 113 K
0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn724+ CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.932, T_max = 0.965
16159 measured reflections
6636 independent reflections
4821 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.138
S = 1.07
6636 reflections
507 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O5ⁱ	0.95	2.37	3.314 (4)	172
C20—H20⋯O10ⁱⁱ	0.95	2.50	3.450 (4)	173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z.

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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811049774/hb6513sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049774/hb6513Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811049774/hb6513Isup3.cml

checkCIF report

Related literature top

For the biological activity of related compounds and for related structures, see: Liu et al. (2011a,b,c,d). For further synthetic details, see: Cho et al. (2010).

Experimental top

The title compound was prepared according to the literature procedures (Cho et al., 2010). Colourless blocks of (I) were grown from slow evaporation of ethanol solution at room temperature.

Structure description top

For the biological activity of related compounds and for related structures, see: Liu et al. (2011a,b,c,d). For further synthetic details, see: Cho et al. (2010).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level.

Ethyl 4-[(4-chlorophenoxy)methyl]-2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate top

Crystal data top

C₁₉H₁₅ClN₂O₅S	Z = 4
M_r = 418.84	F(000) = 864
Triclinic, P1	D_x = 1.510 Mg m⁻³
a = 7.658 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.736 (2) Å	Cell parameters from 5373 reflections
c = 31.462 (9) Å	θ = 2.0–28.0°
α = 95.414 (8)°	µ = 0.36 mm⁻¹
β = 93.595 (13)°	T = 113 K
γ = 95.536 (9)°	Block, colorless
V = 1841.9 (9) Å³	0.20 × 0.18 × 0.10 mm

Data collection top

Rigaku Saturn724+ CCD diffractometer	6636 independent reflections
Radiation source: fine-focus sealed tube	4821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 28.5714 pixels mm^-1	θ_max = 25.3°, θ_min = 2.0°
profile data from ω–scans	h = −9→9
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −9→9
T_min = 0.932, T_max = 0.965	l = −34→37
16159 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0487P)²] where P = (F_o² + 2F_c²)/3
6636 reflections	(Δ/σ)_max < 0.001
507 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

C₁₉H₁₅ClN₂O₅S	γ = 95.536 (9)°
M_r = 418.84	V = 1841.9 (9) Å³
Triclinic, P1	Z = 4
a = 7.658 (2) Å	Mo Kα radiation
b = 7.736 (2) Å	µ = 0.36 mm⁻¹
c = 31.462 (9) Å	T = 113 K
α = 95.414 (8)°	0.20 × 0.18 × 0.10 mm
β = 93.595 (13)°

Data collection top

Rigaku Saturn724+ CCD diffractometer	6636 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	4821 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.965	R_int = 0.054
16159 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.138	H-atom parameters constrained
S = 1.07	Δρ_max = 0.70 e Å⁻³
6636 reflections	Δρ_min = −0.54 e Å⁻³
507 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.06288 (14)	0.22346 (16)	0.14799 (3)	0.0624 (3)
Cl2	0.75805 (14)	0.89132 (14)	0.35049 (3)	0.0543 (3)
S1	0.31213 (10)	0.60383 (11)	0.47252 (2)	0.0282 (2)
S2	0.38418 (10)	0.69544 (11)	0.02723 (2)	0.0270 (2)
O1	−0.2945 (3)	0.9265 (4)	0.62204 (8)	0.0494 (7)
O2	−0.4697 (3)	0.9946 (3)	0.57059 (8)	0.0458 (7)
O3	0.1342 (3)	0.4482 (3)	0.33207 (7)	0.0371 (6)
O4	0.5159 (3)	0.4840 (3)	0.36414 (7)	0.0329 (6)
O5	0.5999 (3)	0.4344 (4)	0.43078 (7)	0.0481 (7)
O6	0.0810 (3)	1.2838 (4)	−0.12206 (7)	0.0473 (7)
O7	0.0164 (3)	1.4680 (3)	−0.07058 (7)	0.0431 (6)
O8	0.5491 (3)	0.8696 (3)	0.16726 (7)	0.0391 (6)
O9	0.4837 (3)	0.4928 (3)	0.13384 (7)	0.0393 (6)
O10	0.5477 (3)	0.4164 (3)	0.06707 (7)	0.0479 (7)
N1	−0.3375 (4)	0.9339 (4)	0.58378 (9)	0.0351 (7)
N2	0.0807 (3)	0.6965 (4)	0.41884 (8)	0.0284 (6)
N3	0.0757 (3)	1.3317 (4)	−0.08384 (9)	0.0329 (7)
N4	0.3024 (3)	0.9408 (4)	0.08080 (8)	0.0269 (6)
C1	0.0473 (4)	0.7472 (4)	0.53661 (10)	0.0273 (8)
H1	0.1548	0.7055	0.5458	0.033*
C2	−0.0636 (4)	0.8068 (4)	0.56656 (10)	0.0292 (8)
H2	−0.0337	0.8070	0.5963	0.035*
C3	−0.2193 (4)	0.8660 (4)	0.55205 (10)	0.0283 (8)
C4	−0.2677 (4)	0.8684 (4)	0.50915 (10)	0.0264 (7)
H4	−0.3748	0.9112	0.5002	0.032*
C5	−0.1574 (4)	0.8076 (4)	0.47948 (10)	0.0264 (8)
H5	−0.1897	0.8060	0.4498	0.032*
C6	0.0014 (4)	0.7483 (4)	0.49283 (9)	0.0258 (7)
C7	0.1180 (4)	0.6887 (4)	0.45996 (10)	0.0257 (8)
C8	0.3452 (4)	0.5764 (4)	0.41898 (9)	0.0265 (8)
C9	0.2093 (4)	0.6326 (4)	0.39547 (10)	0.0274 (8)
C10	0.1867 (4)	0.6278 (5)	0.34789 (9)	0.0337 (8)
H10A	0.0954	0.7027	0.3394	0.040*
H10B	0.2985	0.6696	0.3362	0.040*
C11	0.1246 (4)	0.4053 (5)	0.28864 (10)	0.0325 (8)
C12	0.0871 (4)	0.2302 (5)	0.27464 (11)	0.0414 (9)
H12	0.0740	0.1475	0.2950	0.050*
C13	0.0684 (4)	0.1737 (5)	0.23175 (11)	0.0435 (10)
H13	0.0434	0.0529	0.2224	0.052*
C14	0.0866 (4)	0.2951 (6)	0.20225 (11)	0.0419 (10)
C15	0.1222 (5)	0.4678 (5)	0.21532 (11)	0.0448 (10)
H15	0.1323	0.5494	0.1946	0.054*
C16	0.1441 (4)	0.5272 (5)	0.25884 (11)	0.0400 (9)
H16	0.1717	0.6479	0.2680	0.048*
C17	0.5000 (4)	0.4921 (5)	0.40608 (11)	0.0304 (8)
C18	0.6616 (4)	0.3931 (5)	0.34835 (11)	0.0395 (9)
H18A	0.6565	0.2742	0.3577	0.047*
H18B	0.7758	0.4579	0.3593	0.047*
C19	0.6409 (4)	0.3845 (5)	0.30047 (10)	0.0427 (10)
H19A	0.5281	0.3186	0.2901	0.064*
H19B	0.7370	0.3262	0.2882	0.064*
H19C	0.6440	0.5030	0.2918	0.064*
C20	0.2591 (4)	0.9569 (4)	−0.03709 (9)	0.0254 (7)
H20	0.3027	0.8497	−0.0463	0.030*
C21	0.2033 (4)	1.0641 (4)	−0.06709 (10)	0.0253 (7)
H21	0.2087	1.0325	−0.0969	0.030*
C22	0.1395 (4)	1.2188 (4)	−0.05227 (10)	0.0263 (8)
C23	0.1314 (4)	1.2715 (4)	−0.00937 (9)	0.0260 (7)
H23	0.0880	1.3790	−0.0004	0.031*
C24	0.1879 (4)	1.1641 (4)	0.02008 (10)	0.0258 (7)
H24	0.1835	1.1980	0.0498	0.031*
C25	0.2512 (3)	1.0067 (4)	0.00690 (9)	0.0215 (7)
C26	0.3069 (3)	0.8944 (4)	0.03974 (9)	0.0227 (7)
C27	0.4094 (4)	0.6720 (4)	0.08080 (9)	0.0256 (7)
C28	0.3598 (4)	0.8142 (4)	0.10414 (9)	0.0260 (8)
C29	0.3674 (4)	0.8490 (5)	0.15229 (10)	0.0352 (9)
H29A	0.3119	0.9563	0.1607	0.042*
H29B	0.3043	0.7502	0.1647	0.042*
C30	0.5855 (4)	0.8708 (5)	0.21057 (10)	0.0337 (9)
C31	0.7463 (4)	0.8208 (5)	0.22347 (11)	0.0419 (10)
H31	0.8221	0.7818	0.2026	0.050*
C32	0.7992 (5)	0.8266 (5)	0.26642 (11)	0.0437 (10)
H32	0.9109	0.7929	0.2751	0.052*
C33	0.6870 (5)	0.8826 (5)	0.29680 (10)	0.0385 (9)
C34	0.5246 (4)	0.9283 (5)	0.28490 (11)	0.0379 (9)
H34	0.4479	0.9636	0.3059	0.045*
C35	0.4729 (5)	0.9223 (5)	0.24120 (11)	0.0386 (9)
H35	0.3602	0.9537	0.2325	0.046*
C36	0.4860 (4)	0.5145 (5)	0.09238 (11)	0.0317 (8)
C37	0.5723 (6)	0.3412 (5)	0.14607 (12)	0.0566 (12)
H37A	0.5024	0.2315	0.1338	0.068*
H37B	0.6898	0.3444	0.1345	0.068*
C38	0.5903 (6)	0.3461 (6)	0.19137 (12)	0.0651 (13)
H38A	0.6576	0.4558	0.2034	0.098*
H38B	0.6522	0.2476	0.1994	0.098*
H38C	0.4735	0.3381	0.2025	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0789 (8)	0.0728 (9)	0.0332 (6)	0.0111 (6)	0.0073 (5)	−0.0124 (5)
Cl2	0.0793 (7)	0.0543 (7)	0.0292 (5)	0.0136 (6)	−0.0041 (5)	0.0023 (5)
S1	0.0269 (4)	0.0314 (5)	0.0265 (5)	0.0083 (4)	0.0003 (3)	0.0002 (4)
S2	0.0299 (4)	0.0238 (5)	0.0267 (5)	0.0065 (4)	−0.0012 (3)	−0.0019 (4)
O1	0.0576 (17)	0.063 (2)	0.0317 (15)	0.0229 (14)	0.0142 (12)	0.0032 (13)
O2	0.0411 (15)	0.0510 (19)	0.0493 (16)	0.0228 (13)	0.0121 (12)	0.0010 (13)
O3	0.0433 (14)	0.0385 (16)	0.0268 (13)	−0.0016 (12)	0.0015 (10)	−0.0046 (11)
O4	0.0287 (12)	0.0390 (16)	0.0329 (14)	0.0123 (11)	0.0078 (10)	0.0001 (11)
O5	0.0421 (15)	0.071 (2)	0.0341 (14)	0.0317 (14)	−0.0020 (11)	0.0000 (14)
O6	0.0652 (17)	0.0533 (19)	0.0289 (14)	0.0219 (14)	0.0086 (12)	0.0126 (13)
O7	0.0471 (15)	0.0401 (17)	0.0462 (16)	0.0212 (13)	0.0030 (12)	0.0088 (13)
O8	0.0378 (14)	0.0485 (18)	0.0278 (13)	−0.0048 (12)	−0.0015 (10)	−0.0016 (12)
O9	0.0582 (16)	0.0258 (15)	0.0341 (14)	0.0139 (12)	−0.0096 (11)	0.0026 (11)
O10	0.0687 (18)	0.0373 (17)	0.0391 (15)	0.0269 (14)	−0.0019 (13)	−0.0062 (12)
N1	0.0354 (17)	0.0311 (19)	0.0399 (19)	0.0074 (14)	0.0118 (14)	−0.0004 (15)
N2	0.0306 (15)	0.0284 (17)	0.0264 (15)	0.0072 (12)	0.0024 (12)	−0.0004 (12)
N3	0.0274 (15)	0.038 (2)	0.0357 (18)	0.0065 (14)	0.0037 (12)	0.0100 (14)
N4	0.0283 (15)	0.0282 (17)	0.0250 (15)	0.0064 (12)	0.0047 (11)	0.0014 (12)
C1	0.0223 (16)	0.029 (2)	0.0310 (19)	0.0076 (14)	−0.0013 (13)	0.0005 (15)
C2	0.0328 (18)	0.028 (2)	0.0263 (18)	0.0046 (15)	0.0030 (14)	0.0008 (15)
C3	0.0315 (18)	0.0208 (19)	0.0336 (19)	0.0064 (15)	0.0109 (14)	−0.0009 (15)
C4	0.0234 (17)	0.0211 (19)	0.0341 (19)	0.0030 (14)	0.0013 (14)	−0.0001 (15)
C5	0.0274 (17)	0.024 (2)	0.0271 (18)	0.0039 (14)	0.0002 (13)	−0.0004 (14)
C6	0.0298 (17)	0.0201 (19)	0.0271 (18)	0.0032 (14)	0.0014 (13)	0.0009 (14)
C7	0.0242 (17)	0.0207 (19)	0.0312 (19)	0.0023 (14)	−0.0015 (13)	0.0001 (15)
C8	0.0281 (17)	0.023 (2)	0.0272 (18)	0.0034 (14)	0.0018 (13)	−0.0023 (15)
C9	0.0305 (18)	0.029 (2)	0.0237 (17)	0.0053 (15)	0.0063 (13)	0.0010 (15)
C10	0.0356 (19)	0.038 (2)	0.0285 (19)	0.0097 (17)	0.0048 (14)	−0.0002 (16)
C11	0.0260 (18)	0.044 (2)	0.0272 (19)	0.0087 (16)	0.0039 (14)	−0.0024 (17)
C12	0.046 (2)	0.038 (3)	0.039 (2)	−0.0013 (18)	0.0043 (17)	0.0000 (18)
C13	0.041 (2)	0.042 (3)	0.045 (2)	0.0008 (19)	0.0050 (17)	−0.005 (2)
C14	0.039 (2)	0.055 (3)	0.032 (2)	0.0090 (19)	0.0072 (16)	−0.0057 (19)
C15	0.057 (2)	0.044 (3)	0.036 (2)	0.013 (2)	0.0135 (18)	0.0045 (19)
C16	0.044 (2)	0.044 (3)	0.035 (2)	0.0099 (18)	0.0080 (16)	0.0050 (18)
C17	0.0273 (18)	0.028 (2)	0.035 (2)	0.0039 (15)	0.0023 (15)	−0.0031 (16)
C18	0.0293 (19)	0.044 (3)	0.047 (2)	0.0147 (17)	0.0132 (16)	−0.0025 (18)
C19	0.048 (2)	0.040 (3)	0.042 (2)	0.0097 (18)	0.0189 (17)	0.0019 (18)
C20	0.0247 (17)	0.024 (2)	0.0281 (18)	0.0072 (14)	0.0024 (13)	0.0014 (14)
C21	0.0236 (16)	0.025 (2)	0.0256 (18)	0.0000 (14)	0.0024 (13)	−0.0012 (14)
C22	0.0198 (16)	0.029 (2)	0.0313 (19)	0.0034 (14)	0.0002 (13)	0.0070 (15)
C23	0.0197 (16)	0.026 (2)	0.0318 (19)	0.0017 (14)	0.0022 (13)	0.0004 (15)
C24	0.0228 (16)	0.030 (2)	0.0239 (17)	0.0051 (14)	0.0022 (13)	−0.0019 (15)
C25	0.0164 (15)	0.0236 (19)	0.0235 (17)	−0.0007 (13)	0.0004 (12)	0.0011 (14)
C26	0.0178 (16)	0.0202 (19)	0.0291 (18)	0.0002 (13)	0.0008 (13)	−0.0008 (14)
C27	0.0251 (17)	0.028 (2)	0.0241 (17)	0.0036 (14)	−0.0020 (13)	0.0046 (14)
C28	0.0245 (17)	0.029 (2)	0.0242 (17)	0.0018 (15)	−0.0003 (13)	0.0019 (15)
C29	0.038 (2)	0.037 (2)	0.032 (2)	0.0064 (17)	0.0060 (15)	0.0045 (17)
C30	0.047 (2)	0.028 (2)	0.0230 (18)	−0.0080 (17)	0.0034 (15)	−0.0012 (15)
C31	0.039 (2)	0.051 (3)	0.034 (2)	0.0018 (18)	0.0027 (16)	−0.0033 (19)
C32	0.046 (2)	0.048 (3)	0.037 (2)	0.0106 (19)	0.0025 (17)	−0.0035 (19)
C33	0.062 (2)	0.026 (2)	0.0265 (19)	0.0013 (18)	0.0015 (17)	0.0006 (16)
C34	0.049 (2)	0.032 (2)	0.033 (2)	0.0055 (18)	0.0071 (16)	0.0002 (17)
C35	0.045 (2)	0.037 (2)	0.035 (2)	0.0054 (18)	0.0081 (16)	−0.0008 (17)
C36	0.0324 (19)	0.031 (2)	0.030 (2)	0.0027 (16)	−0.0089 (15)	0.0029 (16)
C37	0.103 (3)	0.026 (2)	0.042 (2)	0.023 (2)	−0.011 (2)	0.0083 (19)
C38	0.090 (3)	0.040 (3)	0.064 (3)	0.015 (2)	−0.025 (2)	0.010 (2)

Geometric parameters (Å, º) top

Cl1—C14	1.737 (3)	C12—H12	0.9500
Cl2—C33	1.735 (3)	C13—C14	1.385 (5)
S1—C8	1.716 (3)	C13—H13	0.9500
S1—C7	1.721 (3)	C14—C15	1.357 (5)
S2—C27	1.713 (3)	C15—C16	1.397 (4)
S2—C26	1.722 (3)	C15—H15	0.9500
O1—N1	1.236 (3)	C16—H16	0.9500
O2—N1	1.222 (3)	C18—C19	1.499 (4)
O3—C11	1.371 (4)	C18—H18A	0.9900
O3—C10	1.441 (4)	C18—H18B	0.9900
O4—C17	1.329 (4)	C19—H19A	0.9800
O4—C18	1.463 (3)	C19—H19B	0.9800
O5—C17	1.202 (4)	C19—H19C	0.9800
O6—N3	1.229 (3)	C20—C21	1.388 (4)
O7—N3	1.235 (3)	C20—C25	1.408 (4)
O8—C30	1.373 (4)	C20—H20	0.9500
O8—C29	1.430 (4)	C21—C22	1.387 (4)
O9—C36	1.332 (4)	C21—H21	0.9500
O9—C37	1.480 (4)	C22—C23	1.380 (4)
O10—C36	1.198 (4)	C23—C24	1.379 (4)
N1—C3	1.483 (4)	C23—H23	0.9500
N2—C7	1.316 (4)	C24—C25	1.391 (4)
N2—C9	1.368 (4)	C24—H24	0.9500
N3—C22	1.475 (4)	C25—C26	1.479 (4)
N4—C26	1.311 (4)	C27—C28	1.363 (4)
N4—C28	1.368 (4)	C27—C36	1.468 (5)
C1—C2	1.384 (4)	C28—C29	1.510 (4)
C1—C6	1.401 (4)	C29—H29A	0.9900
C1—H1	0.9500	C29—H29B	0.9900
C2—C3	1.384 (4)	C30—C31	1.375 (5)
C2—H2	0.9500	C30—C35	1.389 (4)
C3—C4	1.380 (4)	C31—C32	1.381 (4)
C4—C5	1.378 (4)	C31—H31	0.9500
C4—H4	0.9500	C32—C33	1.391 (5)
C5—C6	1.395 (4)	C32—H32	0.9500
C5—H5	0.9500	C33—C34	1.365 (5)
C6—C7	1.478 (4)	C34—C35	1.402 (4)
C8—C9	1.368 (4)	C34—H34	0.9500
C8—C17	1.468 (4)	C35—H35	0.9500
C9—C10	1.493 (4)	C37—C38	1.420 (5)
C10—H10A	0.9900	C37—H37A	0.9900
C10—H10B	0.9900	C37—H37B	0.9900
C11—C12	1.382 (5)	C38—H38A	0.9800
C11—C16	1.395 (5)	C38—H38B	0.9800
C12—C13	1.373 (4)	C38—H38C	0.9800

C8—S1—C7	89.05 (15)	H18A—C18—H18B	108.7
C27—S2—C26	89.03 (15)	C18—C19—H19A	109.5
C11—O3—C10	117.6 (3)	C18—C19—H19B	109.5
C17—O4—C18	116.1 (3)	H19A—C19—H19B	109.5
C30—O8—C29	116.6 (2)	C18—C19—H19C	109.5
C36—O9—C37	113.7 (3)	H19A—C19—H19C	109.5
O2—N1—O1	124.3 (3)	H19B—C19—H19C	109.5
O2—N1—C3	118.3 (3)	C21—C20—C25	120.1 (3)
O1—N1—C3	117.5 (3)	C21—C20—H20	119.9
C7—N2—C9	110.5 (3)	C25—C20—H20	119.9
O6—N3—O7	123.3 (3)	C20—C21—C22	118.0 (3)
O6—N3—C22	118.3 (3)	C20—C21—H21	121.0
O7—N3—C22	118.4 (3)	C22—C21—H21	121.0
C26—N4—C28	110.4 (3)	C23—C22—C21	123.2 (3)
C2—C1—C6	120.1 (3)	C23—C22—N3	118.3 (3)
C2—C1—H1	120.0	C21—C22—N3	118.5 (3)
C6—C1—H1	120.0	C22—C23—C24	118.2 (3)
C1—C2—C3	118.4 (3)	C22—C23—H23	120.9
C1—C2—H2	120.8	C24—C23—H23	120.9
C3—C2—H2	120.8	C23—C24—C25	120.9 (3)
C4—C3—C2	122.7 (3)	C23—C24—H24	119.6
C4—C3—N1	118.3 (3)	C25—C24—H24	119.6
C2—C3—N1	118.9 (3)	C24—C25—C20	119.6 (3)
C5—C4—C3	118.7 (3)	C24—C25—C26	118.8 (3)
C5—C4—H4	120.7	C20—C25—C26	121.6 (3)
C3—C4—H4	120.7	N4—C26—C25	122.0 (3)
C4—C5—C6	120.3 (3)	N4—C26—S2	115.0 (2)
C4—C5—H5	119.8	C25—C26—S2	122.9 (2)
C6—C5—H5	119.8	C28—C27—C36	133.4 (3)
C5—C6—C1	119.8 (3)	C28—C27—S2	110.2 (3)
C5—C6—C7	118.6 (3)	C36—C27—S2	116.3 (2)
C1—C6—C7	121.6 (3)	C27—C28—N4	115.4 (3)
N2—C7—C6	122.3 (3)	C27—C28—C29	127.3 (3)
N2—C7—S1	115.0 (2)	N4—C28—C29	117.2 (3)
C6—C7—S1	122.6 (2)	O8—C29—C28	107.0 (2)
C9—C8—C17	131.6 (3)	O8—C29—H29A	110.3
C9—C8—S1	110.3 (2)	C28—C29—H29A	110.3
C17—C8—S1	118.0 (2)	O8—C29—H29B	110.3
N2—C9—C8	115.1 (3)	C28—C29—H29B	110.3
N2—C9—C10	117.9 (3)	H29A—C29—H29B	108.6
C8—C9—C10	126.9 (3)	O8—C30—C31	116.4 (3)
O3—C10—C9	106.2 (3)	O8—C30—C35	124.2 (3)
O3—C10—H10A	110.5	C31—C30—C35	119.4 (3)
C9—C10—H10A	110.5	C30—C31—C32	120.8 (3)
O3—C10—H10B	110.5	C30—C31—H31	119.6
C9—C10—H10B	110.5	C32—C31—H31	119.6
H10A—C10—H10B	108.7	C31—C32—C33	119.3 (4)
O3—C11—C12	116.3 (3)	C31—C32—H32	120.4
O3—C11—C16	124.0 (3)	C33—C32—H32	120.4
C12—C11—C16	119.7 (3)	C34—C33—C32	121.2 (3)
C13—C12—C11	121.0 (4)	C34—C33—Cl2	120.6 (3)
C13—C12—H12	119.5	C32—C33—Cl2	118.3 (3)
C11—C12—H12	119.5	C33—C34—C35	119.0 (3)
C12—C13—C14	119.1 (4)	C33—C34—H34	120.5
C12—C13—H13	120.4	C35—C34—H34	120.5
C14—C13—H13	120.4	C30—C35—C34	120.4 (3)
C15—C14—C13	120.8 (3)	C30—C35—H35	119.8
C15—C14—Cl1	120.1 (3)	C34—C35—H35	119.8
C13—C14—Cl1	119.1 (3)	O10—C36—O9	123.2 (3)
C14—C15—C16	120.8 (4)	O10—C36—C27	123.2 (3)
C14—C15—H15	119.6	O9—C36—C27	113.7 (3)
C16—C15—H15	119.6	C38—C37—O9	109.6 (3)
C11—C16—C15	118.5 (4)	C38—C37—H37A	109.8
C11—C16—H16	120.7	O9—C37—H37A	109.8
C15—C16—H16	120.7	C38—C37—H37B	109.8
O5—C17—O4	123.8 (3)	O9—C37—H37B	109.8
O5—C17—C8	123.5 (3)	H37A—C37—H37B	108.2
O4—C17—C8	112.7 (3)	C37—C38—H38A	109.5
O4—C18—C19	106.2 (3)	C37—C38—H38B	109.5
O4—C18—H18A	110.5	H38A—C38—H38B	109.5
C19—C18—H18A	110.5	C37—C38—H38C	109.5
O4—C18—H18B	110.5	H38A—C38—H38C	109.5
C19—C18—H18B	110.5	H38B—C38—H38C	109.5

C6—C1—C2—C3	0.2 (5)	C25—C20—C21—C22	−0.4 (4)
C1—C2—C3—C4	−0.2 (5)	C20—C21—C22—C23	0.9 (4)
C1—C2—C3—N1	−178.6 (3)	C20—C21—C22—N3	−178.5 (3)
O2—N1—C3—C4	−2.4 (5)	O6—N3—C22—C23	−179.2 (3)
O1—N1—C3—C4	178.1 (3)	O7—N3—C22—C23	−0.5 (4)
O2—N1—C3—C2	176.1 (3)	O6—N3—C22—C21	0.3 (4)
O1—N1—C3—C2	−3.4 (5)	O7—N3—C22—C21	178.9 (3)
C2—C3—C4—C5	0.7 (5)	C21—C22—C23—C24	−0.6 (4)
N1—C3—C4—C5	179.2 (3)	N3—C22—C23—C24	178.7 (3)
C3—C4—C5—C6	−1.3 (5)	C22—C23—C24—C25	−0.1 (4)
C4—C5—C6—C1	1.4 (5)	C23—C24—C25—C20	0.5 (4)
C4—C5—C6—C7	−178.3 (3)	C23—C24—C25—C26	−178.8 (3)
C2—C1—C6—C5	−0.8 (5)	C21—C20—C25—C24	−0.2 (4)
C2—C1—C6—C7	178.9 (3)	C21—C20—C25—C26	179.0 (3)
C9—N2—C7—C6	−179.7 (3)	C28—N4—C26—C25	179.8 (3)
C9—N2—C7—S1	0.2 (4)	C28—N4—C26—S2	−0.9 (3)
C5—C6—C7—N2	2.9 (5)	C24—C25—C26—N4	−1.8 (4)
C1—C6—C7—N2	−176.8 (3)	C20—C25—C26—N4	179.0 (3)
C5—C6—C7—S1	−177.0 (2)	C24—C25—C26—S2	179.0 (2)
C1—C6—C7—S1	3.3 (4)	C20—C25—C26—S2	−0.3 (4)
C8—S1—C7—N2	−0.2 (3)	C27—S2—C26—N4	0.8 (2)
C8—S1—C7—C6	179.7 (3)	C27—S2—C26—C25	−179.9 (3)
C7—S1—C8—C9	0.1 (3)	C26—S2—C27—C28	−0.4 (2)
C7—S1—C8—C17	−176.7 (3)	C26—S2—C27—C36	−177.3 (3)
C7—N2—C9—C8	−0.2 (4)	C36—C27—C28—N4	176.2 (3)
C7—N2—C9—C10	178.7 (3)	S2—C27—C28—N4	0.0 (3)
C17—C8—C9—N2	176.2 (3)	C36—C27—C28—C29	−1.5 (6)
S1—C8—C9—N2	0.0 (4)	S2—C27—C28—C29	−177.6 (2)
C17—C8—C9—C10	−2.6 (6)	C26—N4—C28—C27	0.6 (4)
S1—C8—C9—C10	−178.7 (3)	C26—N4—C28—C29	178.5 (2)
C11—O3—C10—C9	−172.6 (2)	C30—O8—C29—C28	−168.5 (3)
N2—C9—C10—O3	−104.0 (3)	C27—C28—C29—O8	65.7 (4)
C8—C9—C10—O3	74.7 (4)	N4—C28—C29—O8	−111.9 (3)
C10—O3—C11—C12	175.2 (3)	C29—O8—C30—C31	154.8 (3)
C10—O3—C11—C16	−7.1 (4)	C29—O8—C30—C35	−26.7 (5)
O3—C11—C12—C13	177.7 (3)	O8—C30—C31—C32	176.5 (3)
C16—C11—C12—C13	−0.1 (5)	C35—C30—C31—C32	−2.1 (6)
C11—C12—C13—C14	−0.4 (5)	C30—C31—C32—C33	0.5 (6)
C12—C13—C14—C15	−0.1 (5)	C31—C32—C33—C34	1.3 (6)
C12—C13—C14—Cl1	180.0 (3)	C31—C32—C33—Cl2	−179.2 (3)
C13—C14—C15—C16	1.0 (6)	C32—C33—C34—C35	−1.5 (6)
Cl1—C14—C15—C16	−179.1 (3)	Cl2—C33—C34—C35	179.0 (3)
O3—C11—C16—C15	−176.6 (3)	O8—C30—C35—C34	−176.6 (3)
C12—C11—C16—C15	1.0 (5)	C31—C30—C35—C34	1.8 (5)
C14—C15—C16—C11	−1.5 (5)	C33—C34—C35—C30	0.0 (5)
C18—O4—C17—O5	2.2 (5)	C37—O9—C36—O10	2.9 (5)
C18—O4—C17—C8	−176.8 (3)	C37—O9—C36—C27	−175.8 (3)
C9—C8—C17—O5	−172.4 (4)	C28—C27—C36—O10	−167.3 (3)
S1—C8—C17—O5	3.5 (5)	S2—C27—C36—O10	8.7 (5)
C9—C8—C17—O4	6.6 (5)	C28—C27—C36—O9	11.4 (5)
S1—C8—C17—O4	−177.5 (2)	S2—C27—C36—O9	−172.6 (2)
C17—O4—C18—C19	174.1 (3)	C36—O9—C37—C38	169.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.95	2.37	3.314 (4)	172
C20—H20···O10ⁱⁱ	0.95	2.50	3.450 (4)	173

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅ClN₂O₅S
M_r	418.84
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	7.658 (2), 7.736 (2), 31.462 (9)
α, β, γ (°)	95.414 (8), 93.595 (13), 95.536 (9)
V (Å³)	1841.9 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.20 × 0.18 × 0.10

Data collection
Diffractometer	Rigaku Saturn724+ CCD
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.932, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	16159, 6636, 4821
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.138, 1.07
No. of reflections	6636
No. of parameters	507
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.54

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O5ⁱ	0.95	2.37	3.314 (4)	172
C20—H20···O10ⁱⁱ	0.95	2.50	3.450 (4)	173

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

Acknowledgements

This work was supported financially by the National Natural Science Funds of China (grant No. 21102103), the China Postdoctoral Science Foundation (grant No. 2011M500532), the General Program of the National Natural Science Foundation of China (grant No. 20972112), the Research Fund for the Doctoral Program of Higher Education of China (grant No. 20091202110010) and the Key Program of Tianjin Municipal Natural Science Foundation (grant No. 09JCZDJC21600).

References

Cho, D., Ahn, J., De Castro, K. A., Ahn, H. & Rhee, H. (2010). Tetrahedron, 66, 5583–5588. Web of Science CrossRef CAS Google Scholar
Liu, H.-J., Weng, J.-Q., Tan, C.-X. & Liu, X.-H. (2011b). Acta Cryst. E67, o1940. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, X.-H., Pan, L., Ma, Y., Jian, Q.-W., Tan, C.-X., Li, Y. H., Shi, Y.-X., Li, B.-J., Li, Z.-M. & Zhang, Y.-G. (2011c). Chem. Biol. Drug Des. 78, 689–694. Web of Science CrossRef CAS PubMed Google Scholar
Liu, X.-H., Pan, L., Tan, C.-X., Weng, J.-Q., Wang, B.-L. & Li, Z.-M. (2011a). Pestic. BioChem. Phys. 101, 143–147. Web of Science CrossRef CAS Google Scholar
Liu, X.-H., Tan, C.-X. & Jian, Q.-W. (2011d). Phosphorus Sulfur, 186, 552–557. Web of Science CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Ethyl 4-[(4-chloro­phen­­oxy)meth­yl]-2-(4-nitro­phen­yl)-1,3-thia­zole-5-carboxyl­ate

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Ethyl 4-[(4-chlorophenoxy)methyl]-2-(4-nitrophenyl)-1,3-thiazole-5-carboxylate