Ethyl 5-(4-chloro­phen­yl)-2-[(Z)-(methoxy­carbon­yl)methyl­ene]-7-methyl-3-oxo-3,5-dihydro-2H-thia­zolo[3,2-a]pyrimi­dine-6-carboxyl­ate

Hou, Z.-H.; Zhou, N.-B.; He, B.-H.; Li, X.-F.

doi:10.1107/S1600536809002451

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o375

doi:10.1107/S1600536809002451

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Ethyl 5-(4-chlorophenyl)-2-[(Z)-(methoxycarbonyl)methylene]-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate

Zhao-Hui Hou,^a ^* Ning-Bo Zhou,^a Bin-Hong He ^a and Xiao-Fang Li ^b

^aDepartment of Chemistry and Chemical Engineering, Hunan Institute of Science and Technology, Yueyang 414000, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, People's Republic of China
^*Correspondence e-mail: houzhaohui1972@163.com

(Received 14 January 2009; accepted 20 January 2009; online 23 January 2009)

The title compound, C₁₉H₁₇ClN₂O₅S, was synthesized by the reaction of ethyl 6-(4-chlorophenyl)-2-mercapto-4-methyl-1,6-dihydropyrimidine-5-carboxylate and dimethyl acetylenedicarboxylate in methanol. In the molecule, the nearly planar thiazole ring, with a mean deviation from the plane of 0.0108 (3) Å, is fused with a dihydropyrimidine ring in a flattened half-chair conformation.

Related literature

For the biological activity of fused pyrimidine derivatives, see: Ashok et al. (2007 ); Monks et al. (1991 ). For structures containing a fused pyrimidine ring, see: Liu et al. (2004 ); Sridhar et al. (2006 ); Hou (2009 ).

Experimental

Crystal data

C₁₉H₁₇ClN₂O₅S
M_r = 420.86
Triclinic, $[P \overline 1]$
a = 9.6687 (19) Å
b = 11.052 (2) Å
c = 11.064 (2) Å
α = 108.04 (3)°
β = 104.70 (3)°
γ = 111.82 (3)°
V = 948.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 113 (2) K
0.20 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.934, T_max = 0.966
6937 measured reflections
3324 independent reflections
2622 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.090
S = 1.08
3324 reflections
256 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrystalClear (Rigaku, 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 I, global. DOI: 10.1107/S1600536809002451/fl2231sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002451/fl2231Isup2.hkl

checkCIF report

Comment top

Fused pyrimidine derivatives represent important target molecules due to their highly pronounced biological properties. (Ashok et al., 2007; Monks et al., 1991). In this paper, the structure of the title compound (I) is reported (Fig. 1).

The thiazole ring (C5—N1—C15—C16—S1) has the usual essentially planar geometry observed in other fused thiazolopyrimidine compounds (Liu et al., 2004; Sridhar et al., 2006; Hou, 2009). The thiazole ring makes a dihedral angles of 90.3 (2) ° with the benzene ring (C9–C14). The pyrimidine ring adopts a flattened half-chair conformation. The C16—C17 double bond exist in the Z configuration. Molecular packing (Fig. 2) is stabilized mainly by weak van der Waals forces.

Related literature top

For biological activity of fused pyrimidine derivatives, see: Ashok et al. (2007); Monks et al. (1991). For crystals containing fused pyrimidine, see: Liu et al. (2004); Sridhar et al. (2006); Hou (2009).

Experimental top

A mixture of ethyl 2-mercapto-4-methyl-6-(4-chlorophenyl)-1,6- dihydro-pyrimidine-5-carboxylate (0.01 mol), dimethyl acetylenedicarboxylate (0.01 mol) in methanol (25 ml) was refluxed for 3 h. The reaction mixture was cooled and filtered. The resulting solid was collected and crystallized from methanol to obtain the final product (90% yield, mp 434–435 K). ¹H NMR (CDCl₃, p.p.m.): 1.20 (t, J=7.0 Hz, 3H), 2.53 (s, 3H), 3.86 (s, 3H), 4.10–4.12 (m, 2H), 6.12 (s, 1H), 6.90 (s, 1H), 7.28–7.32 (m, 4H); The compound was recrystallized by slow evaporation of a methanol solution, yielding yellow, blocklike single crystals suitable for X–ray diffraction.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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), drawn with 30% probability ellipsoids. H atoms have been omitted for clarity.
	Fig. 2. The crystal structure of (I), viewed along a axis.

Ethyl 5-(4-chlorophenyl)-2-[(Z)-(methoxycarbonyl)methylene]-7-methyl-3-oxo- 3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate top

Crystal data top

C₁₉H₁₇ClN₂O₅S	Z = 2
M_r = 420.86	F(000) = 436
Triclinic, P1	D_x = 1.474 Mg m⁻³
a = 9.6687 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.052 (2) Å	Cell parameters from 3131 reflections
c = 11.064 (2) Å	θ = 2.1–27.9°
α = 108.04 (3)°	µ = 0.35 mm⁻¹
β = 104.70 (3)°	T = 113 K
γ = 111.82 (3)°	Block, yellow
V = 948.2 (3) Å³	0.20 × 0.14 × 0.10 mm

Data collection top

Rigaku Saturn diffractometer	3324 independent reflections
Radiation source: rotating anode	2622 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.025
ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −11→11
T_min = 0.934, T_max = 0.966	k = −13→13
6937 measured reflections	l = −11→13

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0541P)²] where P = (F_o² + 2F_c²)/3
3324 reflections	(Δ/σ)_max = 0.005
256 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₁₉H₁₇ClN₂O₅S	γ = 111.82 (3)°
M_r = 420.86	V = 948.2 (3) Å³
Triclinic, P1	Z = 2
a = 9.6687 (19) Å	Mo Kα radiation
b = 11.052 (2) Å	µ = 0.35 mm⁻¹
c = 11.064 (2) Å	T = 113 K
α = 108.04 (3)°	0.20 × 0.14 × 0.10 mm
β = 104.70 (3)°

Data collection top

Rigaku Saturn diffractometer	3324 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2622 reflections with I > 2σ(I)
T_min = 0.934, T_max = 0.966	R_int = 0.025
6937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
3324 reflections	Δρ_min = −0.31 e Å⁻³
256 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
S1	0.27994 (5)	0.74177 (5)	0.87884 (4)	0.01936 (13)
Cl1	0.83796 (7)	0.55727 (6)	0.46536 (6)	0.04201 (17)
O1	0.64107 (15)	1.21151 (13)	0.64452 (12)	0.0252 (3)
O2	0.83679 (14)	1.16857 (12)	0.74775 (11)	0.0186 (3)
O3	0.73679 (14)	0.84993 (13)	0.99591 (12)	0.0221 (3)
O4	0.19590 (15)	0.58671 (13)	1.02307 (12)	0.0243 (3)
O5	0.35078 (15)	0.50934 (13)	1.13158 (13)	0.0262 (3)
N1	0.54957 (16)	0.88470 (15)	0.85693 (13)	0.0157 (3)
N2	0.31742 (17)	0.89611 (16)	0.73589 (14)	0.0200 (3)
C1	0.3241 (2)	1.0508 (2)	0.62209 (18)	0.0232 (4)
H1A	0.3709	1.1541	0.6765	0.035*
H1B	0.2115	1.0024	0.6075	0.035*
H1C	0.3300	1.0314	0.5333	0.035*
C2	0.4179 (2)	0.99530 (18)	0.69891 (16)	0.0178 (4)
C3	0.5774 (2)	1.03422 (18)	0.73312 (16)	0.0158 (4)
C4	0.6610 (2)	0.96835 (18)	0.80727 (17)	0.0158 (4)
H4	0.7612	1.0482	0.8889	0.019*
C5	0.3874 (2)	0.85167 (18)	0.81262 (16)	0.0170 (4)
C6	0.6833 (2)	1.14651 (18)	0.70222 (16)	0.0173 (4)
C7	0.9543 (2)	1.27881 (19)	0.72632 (19)	0.0233 (4)
H7A	0.9846	1.3759	0.7921	0.028*
H7B	0.9079	1.2670	0.6320	0.028*
C8	1.1019 (2)	1.2568 (2)	0.7497 (2)	0.0328 (5)
H8A	1.1400	1.2595	0.8401	0.049*
H8B	1.1874	1.3330	0.7455	0.049*
H8C	1.0723	1.1640	0.6786	0.049*
C9	0.7070 (2)	0.86924 (18)	0.71575 (17)	0.0155 (4)
C10	0.8681 (2)	0.89652 (19)	0.76003 (18)	0.0210 (4)
H10	0.9482	0.9778	0.8434	0.025*
C11	0.9108 (2)	0.8038 (2)	0.6811 (2)	0.0253 (4)
H11	1.0189	0.8226	0.7102	0.030*
C12	0.7895 (2)	0.6831 (2)	0.5585 (2)	0.0254 (4)
C13	0.6299 (2)	0.6568 (2)	0.50944 (19)	0.0236 (4)
H13	0.5509	0.5776	0.4242	0.028*
C14	0.5891 (2)	0.75084 (18)	0.58961 (17)	0.0186 (4)
H14	0.4818	0.7340	0.5582	0.022*
C15	0.5986 (2)	0.82795 (18)	0.94441 (16)	0.0167 (4)
C16	0.4553 (2)	0.73775 (18)	0.96435 (17)	0.0178 (4)
C17	0.4656 (2)	0.66465 (18)	1.04032 (17)	0.0193 (4)
H17	0.5632	0.6650	1.0787	0.023*
C18	0.3229 (2)	0.58440 (18)	1.06279 (17)	0.0200 (4)
C19	0.2160 (3)	0.4307 (2)	1.1621 (2)	0.0341 (5)
H19A	0.2063	0.4991	1.2332	0.051*
H19B	0.2374	0.3656	1.1945	0.051*
H19C	0.1156	0.3756	1.0787	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0146 (2)	0.0231 (3)	0.0214 (2)	0.0090 (2)	0.00922 (19)	0.0103 (2)
Cl1	0.0664 (4)	0.0408 (3)	0.0612 (4)	0.0422 (3)	0.0514 (3)	0.0323 (3)
O1	0.0212 (7)	0.0253 (7)	0.0322 (7)	0.0122 (6)	0.0078 (6)	0.0180 (6)
O2	0.0143 (6)	0.0174 (6)	0.0248 (6)	0.0073 (5)	0.0076 (5)	0.0112 (5)
O3	0.0144 (7)	0.0281 (7)	0.0257 (7)	0.0108 (6)	0.0070 (5)	0.0152 (6)
O4	0.0203 (7)	0.0257 (7)	0.0259 (7)	0.0094 (6)	0.0118 (6)	0.0108 (6)
O5	0.0321 (8)	0.0242 (7)	0.0363 (7)	0.0160 (7)	0.0232 (7)	0.0200 (6)
N1	0.0134 (8)	0.0181 (8)	0.0170 (7)	0.0084 (7)	0.0066 (6)	0.0083 (6)
N2	0.0156 (8)	0.0245 (9)	0.0232 (8)	0.0119 (7)	0.0087 (6)	0.0115 (7)
C1	0.0180 (10)	0.0290 (11)	0.0252 (9)	0.0152 (9)	0.0066 (8)	0.0127 (8)
C2	0.0195 (10)	0.0186 (9)	0.0140 (8)	0.0110 (8)	0.0062 (7)	0.0045 (7)
C3	0.0169 (9)	0.0153 (9)	0.0147 (8)	0.0099 (8)	0.0053 (7)	0.0047 (7)
C4	0.0120 (9)	0.0165 (9)	0.0173 (8)	0.0058 (7)	0.0054 (7)	0.0079 (7)
C5	0.0129 (9)	0.0164 (9)	0.0173 (8)	0.0066 (8)	0.0064 (7)	0.0032 (7)
C6	0.0175 (9)	0.0162 (9)	0.0150 (8)	0.0092 (8)	0.0049 (7)	0.0037 (7)
C7	0.0163 (10)	0.0206 (10)	0.0287 (10)	0.0040 (8)	0.0071 (8)	0.0143 (8)
C8	0.0212 (11)	0.0423 (13)	0.0442 (12)	0.0149 (10)	0.0168 (9)	0.0284 (11)
C9	0.0165 (9)	0.0172 (9)	0.0204 (9)	0.0103 (8)	0.0101 (7)	0.0130 (7)
C10	0.0167 (10)	0.0217 (10)	0.0292 (10)	0.0099 (8)	0.0106 (8)	0.0152 (8)
C11	0.0205 (10)	0.0301 (11)	0.0445 (12)	0.0179 (9)	0.0220 (9)	0.0253 (10)
C12	0.0403 (12)	0.0271 (11)	0.0373 (11)	0.0257 (10)	0.0311 (10)	0.0240 (9)
C13	0.0311 (11)	0.0199 (10)	0.0236 (9)	0.0137 (9)	0.0141 (8)	0.0104 (8)
C14	0.0175 (10)	0.0200 (9)	0.0211 (9)	0.0102 (8)	0.0086 (8)	0.0110 (8)
C15	0.0192 (10)	0.0156 (9)	0.0143 (8)	0.0095 (8)	0.0067 (7)	0.0048 (7)
C16	0.0160 (9)	0.0166 (9)	0.0168 (8)	0.0077 (8)	0.0075 (7)	0.0027 (7)
C17	0.0196 (10)	0.0185 (9)	0.0190 (9)	0.0100 (8)	0.0081 (8)	0.0064 (7)
C18	0.0235 (10)	0.0166 (9)	0.0165 (9)	0.0090 (8)	0.0091 (8)	0.0040 (7)
C19	0.0415 (13)	0.0302 (12)	0.0459 (12)	0.0164 (11)	0.0317 (11)	0.0252 (10)

Geometric parameters (Å, º) top

S1—C16	1.7436 (17)	C7—C8	1.507 (2)
S1—C5	1.7582 (17)	C7—H7A	0.9700
Cl1—C12	1.7484 (18)	C7—H7B	0.9700
O1—C6	1.2084 (18)	C8—H8A	0.9600
O2—C6	1.338 (2)	C8—H8B	0.9600
O2—C7	1.4556 (19)	C8—H8C	0.9600
O3—C15	1.2063 (19)	C9—C14	1.383 (3)
O4—C18	1.208 (2)	C9—C10	1.389 (2)
O5—C18	1.3390 (19)	C10—C11	1.388 (2)
O5—C19	1.460 (2)	C10—H10	0.9300
N1—C5	1.380 (2)	C11—C12	1.380 (3)
N1—C15	1.385 (2)	C11—H11	0.9300
N1—C4	1.4804 (19)	C12—C13	1.380 (3)
N2—C5	1.278 (2)	C13—C14	1.390 (2)
N2—C2	1.415 (2)	C13—H13	0.9300
C1—C2	1.506 (2)	C14—H14	0.9300
C1—H1A	0.9600	C15—C16	1.492 (2)
C1—H1B	0.9600	C16—C17	1.344 (2)
C1—H1C	0.9600	C17—C18	1.467 (2)
C2—C3	1.348 (2)	C17—H17	0.9300
C3—C6	1.484 (2)	C19—H19A	0.9600
C3—C4	1.525 (2)	C19—H19B	0.9600
C4—C9	1.525 (2)	C19—H19C	0.9600
C4—H4	0.9800

C16—S1—C5	90.62 (8)	C7—C8—H8C	109.5
C6—O2—C7	116.24 (12)	H8A—C8—H8C	109.5
C18—O5—C19	115.21 (14)	H8B—C8—H8C	109.5
C5—N1—C15	115.79 (14)	C14—C9—C10	119.53 (15)
C5—N1—C4	121.86 (13)	C14—C9—C4	120.55 (14)
C15—N1—C4	122.26 (13)	C10—C9—C4	119.91 (16)
C5—N2—C2	116.82 (14)	C11—C10—C9	120.70 (18)
C2—C1—H1A	109.5	C11—C10—H10	119.7
C2—C1—H1B	109.5	C9—C10—H10	119.7
H1A—C1—H1B	109.5	C12—C11—C10	118.56 (16)
C2—C1—H1C	109.5	C12—C11—H11	120.7
H1A—C1—H1C	109.5	C10—C11—H11	120.7
H1B—C1—H1C	109.5	C11—C12—C13	121.80 (16)
C3—C2—N2	122.50 (14)	C11—C12—Cl1	119.10 (14)
C3—C2—C1	126.35 (16)	C13—C12—Cl1	119.07 (16)
N2—C2—C1	111.13 (14)	C12—C13—C14	118.87 (18)
C2—C3—C6	121.48 (14)	C12—C13—H13	120.6
C2—C3—C4	122.65 (15)	C14—C13—H13	120.6
C6—C3—C4	115.87 (14)	C9—C14—C13	120.43 (16)
N1—C4—C3	108.32 (12)	C9—C14—H14	119.8
N1—C4—C9	109.42 (13)	C13—C14—H14	119.8
C3—C4—C9	113.84 (12)	O3—C15—N1	124.33 (15)
N1—C4—H4	108.4	O3—C15—C16	126.19 (14)
C3—C4—H4	108.4	N1—C15—C16	109.48 (13)
C9—C4—H4	108.4	C17—C16—C15	122.53 (15)
N2—C5—N1	126.49 (15)	C17—C16—S1	125.85 (14)
N2—C5—S1	121.06 (13)	C15—C16—S1	111.62 (11)
N1—C5—S1	112.42 (11)	C16—C17—C18	120.08 (15)
O1—C6—O2	123.10 (15)	C16—C17—H17	120.0
O1—C6—C3	126.17 (15)	C18—C17—H17	120.0
O2—C6—C3	110.73 (13)	O4—C18—O5	124.64 (15)
O2—C7—C8	106.32 (13)	O4—C18—C17	123.25 (15)
O2—C7—H7A	110.5	O5—C18—C17	112.11 (14)
C8—C7—H7A	110.5	O5—C19—H19A	109.5
O2—C7—H7B	110.5	O5—C19—H19B	109.5
C8—C7—H7B	110.5	H19A—C19—H19B	109.5
H7A—C7—H7B	108.7	O5—C19—H19C	109.5
C7—C8—H8A	109.5	H19A—C19—H19C	109.5
C7—C8—H8B	109.5	H19B—C19—H19C	109.5
H8A—C8—H8B	109.5

C5—N2—C2—C3	4.8 (2)	C3—C4—C9—C14	−56.3 (2)
C5—N2—C2—C1	−173.86 (14)	N1—C4—C9—C10	−114.05 (16)
N2—C2—C3—C6	−175.50 (14)	C3—C4—C9—C10	124.61 (16)
C1—C2—C3—C6	2.9 (3)	C14—C9—C10—C11	−1.9 (2)
N2—C2—C3—C4	3.6 (2)	C4—C9—C10—C11	177.13 (13)
C1—C2—C3—C4	−178.02 (15)	C9—C10—C11—C12	−0.7 (2)
C5—N1—C4—C3	12.4 (2)	C10—C11—C12—C13	3.4 (2)
C15—N1—C4—C3	−171.19 (13)	C10—C11—C12—Cl1	−174.78 (11)
C5—N1—C4—C9	−112.22 (16)	C11—C12—C13—C14	−3.3 (2)
C15—N1—C4—C9	64.19 (19)	Cl1—C12—C13—C14	174.86 (12)
C2—C3—C4—N1	−11.4 (2)	C10—C9—C14—C13	2.0 (2)
C6—C3—C4—N1	167.76 (13)	C4—C9—C14—C13	−177.04 (13)
C2—C3—C4—C9	110.58 (18)	C12—C13—C14—C9	0.5 (2)
C6—C3—C4—C9	−70.30 (19)	C5—N1—C15—O3	−177.63 (15)
C2—N2—C5—N1	−3.7 (2)	C4—N1—C15—O3	5.8 (2)
C2—N2—C5—S1	174.06 (11)	C5—N1—C15—C16	2.09 (19)
C15—N1—C5—N2	177.49 (15)	C4—N1—C15—C16	−174.52 (13)
C4—N1—C5—N2	−5.9 (3)	O3—C15—C16—C17	−2.8 (3)
C15—N1—C5—S1	−0.44 (18)	N1—C15—C16—C17	177.46 (15)
C4—N1—C5—S1	176.18 (11)	O3—C15—C16—S1	176.86 (14)
C16—S1—C5—N2	−179.16 (14)	N1—C15—C16—S1	−2.86 (16)
C16—S1—C5—N1	−1.10 (13)	C5—S1—C16—C17	−178.09 (16)
C7—O2—C6—O1	1.0 (2)	C5—S1—C16—C15	2.24 (12)
C7—O2—C6—C3	−178.78 (13)	C15—C16—C17—C18	176.57 (14)
C2—C3—C6—O1	−0.9 (3)	S1—C16—C17—C18	−3.1 (2)
C4—C3—C6—O1	180.00 (15)	C19—O5—C18—O4	−2.1 (2)
C2—C3—C6—O2	178.93 (14)	C19—O5—C18—C17	177.95 (14)
C4—C3—C6—O2	−0.21 (19)	C16—C17—C18—O4	−4.6 (3)
C6—O2—C7—C8	−165.55 (14)	C16—C17—C18—O5	175.35 (15)
N1—C4—C9—C14	65.01 (17)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇ClN₂O₅S
M_r	420.86
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	9.6687 (19), 11.052 (2), 11.064 (2)
α, β, γ (°)	108.04 (3), 104.70 (3), 111.82 (3)
V (Å³)	948.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.20 × 0.14 × 0.10

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.934, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	6937, 3324, 2622
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.090, 1.08
No. of reflections	3324
No. of parameters	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.31

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

References

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