Ethyl 6-amino-8-(4-chloro­phen­yl)-9-nitro-2,3,4,8-tetra­hydro­pyrido[2,1-b][1,3]thia­zine-7-carboxyl­ate

Zhang, N.; Zhang, X.; Li, D.

doi:10.1107/S1600536811032193

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2352

doi:10.1107/S1600536811032193

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Ethyl 6-amino-8-(4-chlorophenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate

Na Zhang,^a Xian Zhang ^a and Dongmei Li ^b ^*

^aSchool of Materials Science and Engineering, Shandong Institute of Light Industry, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, University of Jinan, People's Republic of China
^*Correspondence e-mail: chm_lidm@ujn.edu.cn

(Received 5 July 2011; accepted 8 August 2011; online 17 August 2011)

In the structure of the title compound, C₁₇H₁₈ClN₃O₄S, the thiazinane ring displays a twist-boat conformation. The 1,4-dihydropyridine ring is approximately perpendicular to the benzene ring [dihedral angle = 88.3 (1)°]. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by N—H⋯O interactions into a C(8) chain along [100].

Related literature

For a related structure, see: Tian et al. (2009 ). For puckering parameters, see: Cremer & Pople 1(975). For background to neonicotinoid insecticides, see: Mori et al. (2001 ); Kagabu (1997 ); Tian et al. (2007 ); Jeschke & Nauen (2008 ); Tomizawa & Casida (2005 ). For set-graph notation, see: Bernstein et al. (1995 ). For puckering parameters, see: Cremer & Pople (1975 );

Experimental

Crystal data

C₁₇H₁₈ClN₃O₄S
M_r = 395.85
Triclinic, $[P \overline 1]$
a = 8.6376 (8) Å
b = 9.9719 (8) Å
c = 12.0616 (11) Å
α = 110.970 (8)°
β = 103.252 (8)°
γ = 99.663 (7)°
V = 907.88 (16) Å³
Z = 2
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 298 K
0.58 × 0.28 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.821, T_max = 0.946
7457 measured reflections
3692 independent reflections
2856 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.119
S = 1.03
3692 reflections
242 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1	0.89 (4)	1.95 (5)	2.680 (4)	138 (4)
N2—H2A⋯O4ⁱ	0.87 (4)	2.16 (4)	2.850 (3)	137 (4)
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811032193/bx2362sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032193/bx2362Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032193/bx2362Isup3.cml

checkCIF report

Comment top

Neonicotinoids, represented by imidacloprid (IMI) are extensively utilized as systemic insecticides for crop protection against piercing-sucking insect pests, currently accounting for over one-fifth of the world insecticide market (Jeschke et al., 2008). Neonicotinoids act as selective agonists at the insect nicotinic acetylcholine receptor (nAChR), combining excellent insecticidal effectiveness with minimal risk to people and wildlife (Tomizawa et al., 2005). Our interest was introducing sulfur atom into the lead struture and synthesizing a series of new compounds, in which the title compound exhibited moderate insecticidal activities against pea aphids.

Structure of the title compound is shown in Fig. 1 with atom-numbering scheme. the thiazinane ring displays a twist-boat conformation with puckering parameters Q_T= 0.771 (3)Å, θ= 93.0 (2)°, ϕ= 156.9 (3)° (Cremer & Pople, 1975). The 1,4-dihydropyridine ring is almost plane conformation and aproximately perpendicular to the phenyl ring ( dihedral angle of 88.3 (1)°). The molecular conformation is stabilized by one intramolecular N—H···O hydrogen bond. The molecular conformation is stabilized by one intramolecular N—H···O hydrogen bond. The molecules are linked by N—H···O interactions, into a chain along [100] with graph-set notation C(8) (Bernstein et al.,1995), Table 1, Fig. 2.

Related literature top

For a related structure, see: Tian et al. (2009). For puckering parameters, see: Cremer & Pople 1(975). For background to neonicotinoid insecticides, see: Mori et al. (2001); Kagabu (1997); Tian et al. (2007); Jeschke & Nauen (2008); Tomizawa & Casida (2005). For set-graph notation, see: Bernstein et al. (1995). For puckering parameters, see: Cremer & Pople (1975);

Experimental top

A solution of Ethyl cyanoacetate (15 mmol) in anhydrous alcohol (15 ml) was added dropwise to a solution of 4-Chlorobenzaldehyde (15 mmol) in anhydrous alcohol (15 ml) at room temperature. After 5 min of stirring at room temperature, piperidine (0.1 mmol) used as catalyst was added dropwise. The resulting mixture was stirred for another 2 h, then (Z)-2- (nitromethylene)-1,3-thiazinane (10 mmol) was added to the reaction mixture, refluxed for 15–20 h, and cooled to room temperature. Solid crystal products was filtered, washed with CH₂Cl₂, and dried to give desired products. Single crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of dichloromethane and ethyl acetate of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of the title compound with atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The H atoms are shown as spheres of arbitrary size. The hydrogen bond is showing as dashed lines.

Ethyl 6-amino-8-(4-chlorophenyl)-9-nitro-2,3,4,8- tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate top

Crystal data top

C₁₇H₁₈ClN₃O₄S	Z = 2
M_r = 395.85	F(000) = 412
Triclinic, P1	D_x = 1.448 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6376 (8) Å	Cell parameters from 4541 reflections
b = 9.9719 (8) Å	θ = 2.4–27.7°
c = 12.0616 (11) Å	µ = 0.35 mm⁻¹
α = 110.970 (8)°	T = 298 K
β = 103.252 (8)°	Prism, colourless
γ = 99.663 (7)°	0.58 × 0.28 × 0.16 mm
V = 907.88 (16) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	3692 independent reflections
Radiation source: fine-focus sealed tube	2856 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→10
T_min = 0.821, T_max = 0.946	k = −12→12
7457 measured reflections	l = −15→14

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0499P)² + 0.3496P] where P = (F_o² + 2F_c²)/3
3692 reflections	(Δ/σ)_max < 0.001
242 parameters	Δρ_max = 0.30 e Å⁻³
4 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₇H₁₈ClN₃O₄S	γ = 99.663 (7)°
M_r = 395.85	V = 907.88 (16) Å³
Triclinic, P1	Z = 2
a = 8.6376 (8) Å	Mo Kα radiation
b = 9.9719 (8) Å	µ = 0.35 mm⁻¹
c = 12.0616 (11) Å	T = 298 K
α = 110.970 (8)°	0.58 × 0.28 × 0.16 mm
β = 103.252 (8)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3692 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2856 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.946	R_int = 0.021
7457 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3692 reflections	Δρ_min = −0.38 e Å⁻³
242 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	0.55649 (9)	0.69346 (7)	1.02703 (6)	0.0526 (2)
Cl1	−0.06895 (8)	0.51657 (8)	0.27303 (6)	0.0582 (2)
O1	0.7918 (2)	1.0629 (2)	0.70241 (19)	0.0661 (6)
C12	0.0733 (3)	0.6242 (3)	0.4217 (2)	0.0402 (5)
C13	0.1908 (3)	0.5640 (2)	0.4697 (2)	0.0426 (5)
H13	0.1918	0.4665	0.4251	0.051*
C10	0.1846 (3)	0.8525 (3)	0.6042 (2)	0.0415 (5)
H10	0.1810	0.9488	0.6496	0.050*
C15	0.6594 (3)	1.0300 (3)	0.7201 (2)	0.0440 (5)
C14	0.3069 (3)	0.6519 (2)	0.5857 (2)	0.0385 (5)
H14	0.3874	0.6128	0.6183	0.046*
C11	0.0684 (3)	0.7665 (3)	0.4875 (2)	0.0478 (6)
H11	−0.0120	0.8051	0.4543	0.057*
C16	0.5733 (4)	1.1999 (3)	0.6395 (3)	0.0589 (7)
H16A	0.6017	1.1547	0.5639	0.071*
H16B	0.6655	1.2843	0.6994	0.071*
C6	0.7619 (4)	0.6382 (3)	0.8644 (3)	0.0706 (8)
H6A	0.8354	0.6341	0.8141	0.085*
H6B	0.6767	0.5437	0.8247	0.085*
C5	0.7196 (3)	0.8499 (3)	0.8047 (2)	0.0405 (5)
O2	0.53736 (19)	1.09179 (17)	0.69114 (15)	0.0449 (4)
O3	0.2722 (2)	0.75602 (19)	0.98083 (15)	0.0513 (4)
O4	0.21057 (18)	0.91022 (19)	0.89999 (15)	0.0484 (4)
C3	0.4386 (2)	0.8934 (2)	0.78073 (18)	0.0317 (4)
H3	0.4147	0.9901	0.8135	0.038*
N3	0.3003 (2)	0.8315 (2)	0.92150 (16)	0.0373 (4)
C9	0.3064 (2)	0.7963 (2)	0.65422 (18)	0.0312 (4)
C1	0.5529 (3)	0.7644 (2)	0.91386 (19)	0.0347 (5)
N1	0.6833 (2)	0.7590 (2)	0.86615 (17)	0.0422 (4)
C4	0.6108 (2)	0.9223 (2)	0.76932 (19)	0.0354 (5)
C2	0.4350 (2)	0.8266 (2)	0.87397 (18)	0.0311 (4)
C8	0.7765 (4)	0.7224 (4)	1.0854 (3)	0.0815 (10)
H8A	0.8287	0.8291	1.1280	0.098*
H8B	0.7976	0.6811	1.1472	0.098*
N2	0.8663 (3)	0.8554 (3)	0.7814 (2)	0.0656 (7)
H2A	0.943 (3)	0.848 (4)	0.8361	0.068*
H2B	0.895 (4)	0.923 (4)	0.756	0.068*
C17	0.4207 (4)	1.2497 (4)	0.6110 (3)	0.0777 (9)
H17A	0.3289	1.1643	0.5560	0.117*
H17B	0.4372	1.3166	0.5713	0.117*
H17C	0.3982	1.3001	0.6873	0.117*
C7	0.8573 (5)	0.6566 (5)	0.9903 (4)	0.0968 (12)
H7A	0.9679	0.7208	1.0146	0.116*
H7B	0.8672	0.5600	0.9875	0.116*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0649 (4)	0.0527 (4)	0.0599 (4)	0.0256 (3)	0.0266 (3)	0.0369 (3)
Cl1	0.0493 (4)	0.0660 (4)	0.0387 (3)	0.0006 (3)	−0.0040 (3)	0.0164 (3)
O1	0.0412 (10)	0.0883 (14)	0.0853 (14)	0.0094 (9)	0.0283 (10)	0.0529 (12)
C12	0.0315 (11)	0.0478 (13)	0.0337 (11)	−0.0002 (9)	0.0041 (9)	0.0173 (10)
C13	0.0494 (13)	0.0377 (11)	0.0354 (12)	0.0073 (10)	0.0095 (10)	0.0139 (10)
C10	0.0344 (12)	0.0419 (12)	0.0434 (12)	0.0143 (9)	0.0070 (10)	0.0138 (10)
C15	0.0362 (12)	0.0493 (13)	0.0399 (12)	0.0006 (10)	0.0100 (10)	0.0172 (10)
C14	0.0364 (11)	0.0411 (12)	0.0380 (12)	0.0132 (9)	0.0067 (10)	0.0184 (10)
C11	0.0335 (12)	0.0581 (15)	0.0487 (14)	0.0150 (11)	0.0029 (11)	0.0238 (12)
C16	0.0721 (18)	0.0534 (15)	0.0672 (17)	0.0148 (13)	0.0333 (15)	0.0368 (14)
C6	0.087 (2)	0.0748 (19)	0.076 (2)	0.0578 (17)	0.0406 (18)	0.0346 (16)
C5	0.0283 (11)	0.0528 (13)	0.0365 (11)	0.0099 (10)	0.0089 (9)	0.0153 (10)
O2	0.0443 (9)	0.0480 (9)	0.0495 (9)	0.0093 (7)	0.0181 (8)	0.0274 (8)
O3	0.0466 (10)	0.0598 (10)	0.0512 (10)	0.0043 (8)	0.0218 (8)	0.0277 (9)
O4	0.0303 (8)	0.0637 (10)	0.0541 (10)	0.0190 (8)	0.0145 (8)	0.0241 (9)
C3	0.0271 (10)	0.0319 (10)	0.0333 (10)	0.0069 (8)	0.0085 (9)	0.0114 (8)
N3	0.0285 (9)	0.0408 (10)	0.0320 (9)	0.0012 (8)	0.0060 (8)	0.0091 (8)
C9	0.0250 (10)	0.0370 (11)	0.0313 (10)	0.0058 (8)	0.0086 (8)	0.0151 (9)
C1	0.0381 (11)	0.0283 (10)	0.0327 (11)	0.0073 (9)	0.0098 (9)	0.0085 (8)
N1	0.0406 (10)	0.0479 (11)	0.0440 (11)	0.0222 (9)	0.0157 (9)	0.0196 (9)
C4	0.0256 (10)	0.0430 (11)	0.0332 (11)	0.0049 (9)	0.0076 (9)	0.0141 (9)
C2	0.0262 (10)	0.0330 (10)	0.0294 (10)	0.0050 (8)	0.0082 (8)	0.0096 (8)
C8	0.079 (2)	0.125 (3)	0.073 (2)	0.060 (2)	0.0246 (18)	0.062 (2)
N2	0.0324 (11)	0.106 (2)	0.0749 (17)	0.0273 (12)	0.0228 (11)	0.0482 (15)
C17	0.092 (2)	0.082 (2)	0.093 (2)	0.0385 (19)	0.039 (2)	0.059 (2)
C7	0.095 (3)	0.154 (4)	0.104 (3)	0.088 (3)	0.049 (2)	0.088 (3)

Geometric parameters (Å, º) top

S1—C1	1.744 (2)	C6—H6B	0.9700
S1—C8	1.802 (3)	C5—N2	1.356 (3)
Cl1—C12	1.745 (2)	C5—C4	1.361 (3)
O1—C15	1.224 (3)	C5—N1	1.400 (3)
C12—C11	1.369 (3)	O3—N3	1.242 (2)
C12—C13	1.382 (3)	O4—N3	1.242 (2)
C13—C14	1.384 (3)	C3—C2	1.502 (3)
C13—H13	0.9300	C3—C4	1.514 (3)
C10—C11	1.387 (3)	C3—C9	1.531 (3)
C10—C9	1.390 (3)	C3—H3	0.9800
C10—H10	0.9300	N3—C2	1.410 (3)
C15—O2	1.347 (3)	C1—C2	1.362 (3)
C15—C4	1.449 (3)	C1—N1	1.378 (3)
C14—C9	1.382 (3)	C8—C7	1.488 (5)
C14—H14	0.9300	C8—H8A	0.9700
C11—H11	0.9300	C8—H8B	0.9700
C16—O2	1.450 (3)	N2—H2A	0.855 (17)
C16—C17	1.495 (4)	N2—H2B	0.859 (17)
C16—H16A	0.9700	C17—H17A	0.9600
C16—H16B	0.9700	C17—H17B	0.9600
C6—N1	1.475 (3)	C17—H17C	0.9600
C6—C7	1.482 (4)	C7—H7A	0.9700
C6—H6A	0.9700	C7—H7B	0.9700

C1—S1—C8	98.75 (13)	C9—C3—H3	107.7
C11—C12—C13	121.3 (2)	O4—N3—O3	121.78 (18)
C11—C12—Cl1	119.83 (18)	O4—N3—C2	118.18 (17)
C13—C12—Cl1	118.85 (18)	O3—N3—C2	120.02 (18)
C12—C13—C14	118.5 (2)	C14—C9—C10	118.33 (19)
C12—C13—H13	120.7	C14—C9—C3	120.93 (18)
C14—C13—H13	120.7	C10—C9—C3	120.73 (19)
C11—C10—C9	120.8 (2)	C2—C1—N1	119.40 (19)
C11—C10—H10	119.6	C2—C1—S1	124.77 (16)
C9—C10—H10	119.6	N1—C1—S1	115.80 (16)
O1—C15—O2	121.5 (2)	C1—N1—C5	120.12 (18)
O1—C15—C4	126.6 (2)	C1—N1—C6	116.9 (2)
O2—C15—C4	111.94 (18)	C5—N1—C6	122.2 (2)
C9—C14—C13	121.7 (2)	C5—C4—C15	119.96 (19)
C9—C14—H14	119.2	C5—C4—C3	121.27 (19)
C13—C14—H14	119.2	C15—C4—C3	118.76 (19)
C12—C11—C10	119.4 (2)	C1—C2—N3	119.81 (18)
C12—C11—H11	120.3	C1—C2—C3	123.84 (18)
C10—C11—H11	120.3	N3—C2—C3	116.35 (18)
O2—C16—C17	107.0 (2)	C7—C8—S1	116.0 (3)
O2—C16—H16A	110.3	C7—C8—H8A	108.3
C17—C16—H16A	110.3	S1—C8—H8A	108.3
O2—C16—H16B	110.3	C7—C8—H8B	108.3
C17—C16—H16B	110.3	S1—C8—H8B	108.3
H16A—C16—H16B	108.6	H8A—C8—H8B	107.4
N1—C6—C7	113.6 (3)	C5—N2—H2A	115 (2)
N1—C6—H6A	108.8	C5—N2—H2B	114 (2)
C7—C6—H6A	108.8	H2A—N2—H2B	116 (3)
N1—C6—H6B	108.8	C16—C17—H17A	109.5
C7—C6—H6B	108.8	C16—C17—H17B	109.5
H6A—C6—H6B	107.7	H17A—C17—H17B	109.5
N2—C5—C4	124.0 (2)	C16—C17—H17C	109.5
N2—C5—N1	115.0 (2)	H17A—C17—H17C	109.5
C4—C5—N1	121.05 (19)	H17B—C17—H17C	109.5
C15—O2—C16	116.12 (18)	C6—C7—C8	111.6 (3)
C2—C3—C4	109.50 (16)	C6—C7—H7A	109.3
C2—C3—C9	111.93 (15)	C8—C7—H7A	109.3
C4—C3—C9	112.25 (16)	C6—C7—H7B	109.3
C2—C3—H3	107.7	C8—C7—H7B	109.3
C4—C3—H3	107.7	H7A—C7—H7B	108.0

C11—C12—C13—C14	−1.3 (3)	C7—C6—N1—C5	120.1 (3)
Cl1—C12—C13—C14	177.68 (16)	N2—C5—C4—C15	−9.6 (4)
C12—C13—C14—C9	0.8 (3)	N1—C5—C4—C15	172.29 (19)
C13—C12—C11—C10	0.6 (3)	N2—C5—C4—C3	170.7 (2)
Cl1—C12—C11—C10	−178.39 (17)	N1—C5—C4—C3	−7.4 (3)
C9—C10—C11—C12	0.6 (3)	O1—C15—C4—C5	2.2 (4)
O1—C15—O2—C16	−0.7 (3)	O2—C15—C4—C5	−179.4 (2)
C4—C15—O2—C16	−179.22 (19)	O1—C15—C4—C3	−178.1 (2)
C17—C16—O2—C15	178.3 (2)	O2—C15—C4—C3	0.3 (3)
C13—C14—C9—C10	0.4 (3)	C2—C3—C4—C5	20.6 (3)
C13—C14—C9—C3	−178.31 (18)	C9—C3—C4—C5	−104.3 (2)
C11—C10—C9—C14	−1.1 (3)	C2—C3—C4—C15	−159.09 (18)
C11—C10—C9—C3	177.56 (19)	C9—C3—C4—C15	76.0 (2)
C2—C3—C9—C14	−61.2 (2)	N1—C1—C2—N3	179.49 (17)
C4—C3—C9—C14	62.4 (2)	S1—C1—C2—N3	−2.5 (3)
C2—C3—C9—C10	120.2 (2)	N1—C1—C2—C3	−0.9 (3)
C4—C3—C9—C10	−116.2 (2)	S1—C1—C2—C3	177.04 (15)
C8—S1—C1—C2	−152.2 (2)	O4—N3—C2—C1	168.14 (18)
C8—S1—C1—N1	25.8 (2)	O3—N3—C2—C1	−13.3 (3)
C2—C1—N1—C5	17.0 (3)	O4—N3—C2—C3	−11.5 (3)
S1—C1—N1—C5	−161.12 (16)	O3—N3—C2—C3	167.08 (17)
C2—C1—N1—C6	−153.1 (2)	C4—C3—C2—C1	−16.8 (3)
S1—C1—N1—C6	28.7 (3)	C9—C3—C2—C1	108.4 (2)
N2—C5—N1—C1	168.8 (2)	C4—C3—C2—N3	162.84 (16)
C4—C5—N1—C1	−12.9 (3)	C9—C3—C2—N3	−72.0 (2)
N2—C5—N1—C6	−21.6 (3)	C1—S1—C8—C7	−54.3 (3)
C4—C5—N1—C6	156.7 (2)	N1—C6—C7—C8	36.1 (5)
C7—C6—N1—C1	−70.0 (3)	S1—C8—C7—C6	25.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1	0.89 (4)	1.95 (5)	2.680 (4)	138 (4)
N2—H2A···O4ⁱ	0.87 (4)	2.16 (4)	2.850 (3)	137 (4)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈ClN₃O₄S
M_r	395.85
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.6376 (8), 9.9719 (8), 12.0616 (11)
α, β, γ (°)	110.970 (8), 103.252 (8), 99.663 (7)
V (Å³)	907.88 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.58 × 0.28 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.821, 0.946
No. of measured, independent and observed [I > 2σ(I)] reflections	7457, 3692, 2856
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.119, 1.03
No. of reflections	3692
No. of parameters	242
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.38

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1	0.89 (4)	1.95 (5)	2.680 (4)	138 (4)
N2—H2A···O4ⁱ	0.87 (4)	2.16 (4)	2.850 (3)	137 (4)

Symmetry code: (i) x+1, y, z.

Acknowledgements

The authors thank the National Natural Science Foundation of China (grant 20902037) for financial support.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Jeschke, P. & Nauen, R. (2008). Pest Manag. Sci. 64, 1084–1098. Web of Science CrossRef PubMed CAS Google Scholar
Kagabu, S. (1997). Rev. Toxicol. 1, 75–129. CAS Google Scholar
Mori, K., Okumoto, T., Kawahara, N. & Ozoe, Y. (2001). Pest. Manag. Sci. 46, 40–46. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tian, Z., Li, D. & Li, Z. (2009). Acta Cryst. E65, o2517. Web of Science CSD CrossRef IUCr Journals Google Scholar
Tian, Z. Z., Shao, X. S., Li, Z., Qian, X. H. & Huang, Q. C. (2007). J. Agric. Food. Chem. 55, 2288–2292. Web of Science CrossRef PubMed CAS Google Scholar
Tomizawa, M. & Casida, J. E. (2005). Annu. Rev. Pharmacol. Toxicol. 45, 247–268. Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 6-amino-8-(4-chloro­phen­yl)-9-nitro-2,3,4,8-tetra­hydro­pyrido[2,1-b][1,3]thia­zine-7-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 6-amino-8-(4-chlorophenyl)-9-nitro-2,3,4,8-tetrahydropyrido[2,1-b][1,3]thiazine-7-carboxylate