Methyl 2-(2-amino-1,3-thia­zol-4-yl)-2-[(Z)-methoxy­carbonyl­methoxy­imino]ethano­ate

Sharif, S.; Tahir, M.N.; Khan, I.U.; Ahmad, S.; Salariya, M.A.

doi:10.1107/S1600536809007661

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o713

doi:10.1107/S1600536809007661

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Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]ethanoate

Shahzad Sharif,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Sarfraz Ahmad ^c and Manan Ayub Salariya ^c

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cPharmagen Ltd, Lahore 54000, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 1 March 2009; accepted 2 March 2009; online 6 March 2009)

In the molecule of the title compound, C₉H₁₁N₃O₅S, the thiazole ring is oriented at dihedral angles of 87.33 (3) and 87.18 (3)° with respect to the planar (r.m.s. deviations 0.0136 and 0.0139 Å) methyl ester groups. The dihedral angle between the methyl ester groups is 44.20 (3)°. In the crystal structure, intermolecular N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds link the molecules along the a axis, through R₂²(8) and R₂²(22) ring motifs, forming infinite two-dimensional polymeric sheets. π–π Contacts between the thiazole rings [centroid–centroid distance = 3.536 (2) Å] may further stabilize the structure.

Related literature

For general background, see: Fu et al. (2005 ); Saprykina et al. (2006 ). For a related structure, see: Cheng (2007 ). For bond-length data, see: Allen et al. (1987 ). For ring motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₁₁N₃O₅S
M_r = 273.27
Monoclinic, P 2₁ /c
a = 12.240 (2) Å
b = 5.7500 (8) Å
c = 19.887 (3) Å
β = 120.016 (8)°
V = 1211.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.22 × 0.08 × 0.06 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.975, T_max = 0.982
10459 measured reflections
2168 independent reflections
1102 reflections with I > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.124
S = 1.01
2168 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1ⁱ	0.86	2.22	3.057 (5)	163
N2—H2B⋯O5ⁱⁱ	0.86	2.27	3.097 (5)	160
C6—H6A⋯O3ⁱⁱⁱ	0.96	2.53	3.408 (5)	152
C6—H6C⋯O4^iv	0.96	2.51	3.385 (6)	152
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) x, y+1, z; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); 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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007661/hk2639sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809007661/hk2639Isup2.hkl

checkCIF report

Comment top

The title compound belongs to thiazole group of organic compounds. Thiazole derivatives have been widely used as intermediates for the syntheses of pharmaceutical active products (Saprykina et al., 2006). 2-Amino thiazole derivatives are the special compounds, which are used for the syntheses of antibiotics (Fu et al., 2005) such as cephalosporins. We report herein the crystal structure of the title compound, (I), which was obtained by alkolysis of mica ester (S-2-benzothiazolyl(Z)-2-(2-aminothiazole -4-yl)-2-methoxy-carbonylmethoxyiminothioacetate) in methanol.

In the molecule of (I), (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. (I) is different from (Z)-(2-amino- thiazol-1-ium-4-yl)-2-(t-butoxycarbonylmethoxyimino)acetate monohydrate, (II) (Cheng, 2007), due to the attachements at carboxylate groups. In (I), ring A (S1/N1/C1-C3) is, of course, planar, and it is oriented with respect to the planar methyl ester moieties (O1/O2/C5/C6) and (O4/O5/C8/C9) at dihedral angles of 87.33 (3) and 87.18 (3) °, respectively, while the dihedral angle between the methyl ester moieties is 44.20 (3)°.

In the crystal structure, intermolecular N-H···N, N-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. The N-H···N hydrogen bonds link the molecules into dimers by forming the R₂²(8) ring motifs (Bernstein et al., 1995), then N-H···O hydrogen bonds connect the dimers by forming R₂²(22) ring motifs, and C-H···O hydrogen bonds interlink the dimers along the a axis forming infinite two-dimensional polymeric sheets. The π-π contact between the thiazole rings, Cg1—Cg1ⁱ [symmetry code: (i) -x, 1 - y, 1 - z, where Cg1 is centroid of the ring A (S1/N1/C1-C3)] may further stabilize the structure, with centroid-centroid distance of 3.536 (2) Å.

Related literature top

For general background, see: Fu et al. (2005); Saprykina et al. (2006). For a related structure, see: Cheng (2007). For bond-length data, see: Allen et al. (1987). For ring motifs, see: Bernstein et al. (1995).

Experimental top

For the preparation of the title compound, mica ester, S-2-benzo- thiazolyl-(Z)-2-(2-aminothiazole-4-yl)-2-methoxy-carbonylmethoxyimino- thioacetate) (1.0 g, 2.195 mmol) was suspended in methanol (10 ml). The suspension was heated, stirred at pH = 6.5 for 15 min. The clear transparent mixture was allowed to cool at room temperature from which light yellow crystals were obtained after 3 d.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]ethanoate top

Crystal data top

C₉H₁₁N₃O₅S	F(000) = 568
M_r = 273.27	D_x = 1.498 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2168 reflections
a = 12.240 (2) Å	θ = 2.2–25.2°
b = 5.7500 (8) Å	µ = 0.29 mm⁻¹
c = 19.887 (3) Å	T = 296 K
β = 120.016 (8)°	Needle, yellow
V = 1211.9 (3) Å³	0.22 × 0.08 × 0.06 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2168 independent reflections
Radiation source: fine-focus sealed tube	1102 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.100
Detector resolution: 7.80 pixels mm^-1	θ_max = 25.2°, θ_min = 2.2°
ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −6→6
T_min = 0.975, T_max = 0.982	l = −23→23
10459 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0434P)²] where P = (F_o² + 2F_c²)/3
2168 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₉H₁₁N₃O₅S	V = 1211.9 (3) Å³
M_r = 273.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.240 (2) Å	µ = 0.29 mm⁻¹
b = 5.7500 (8) Å	T = 296 K
c = 19.887 (3) Å	0.22 × 0.08 × 0.06 mm
β = 120.016 (8)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	2168 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1102 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.982	R_int = 0.100
10459 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.24 e Å⁻³
2168 reflections	Δρ_min = −0.25 e Å⁻³
163 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.20130 (10)	0.51478 (17)	0.37288 (6)	0.0437 (4)
O1	0.2059 (3)	0.7883 (4)	0.38158 (15)	0.0513 (11)
O2	0.1345 (3)	0.5059 (5)	0.29312 (18)	0.0625 (14)
O3	0.3512 (2)	0.3538 (4)	0.46873 (15)	0.0426 (10)
O4	0.5574 (3)	0.3846 (5)	0.67254 (18)	0.0613 (12)
O5	0.4360 (3)	0.6603 (5)	0.59065 (17)	0.0574 (11)
N1	−0.0076 (3)	0.2430 (5)	0.43907 (18)	0.0351 (11)
N2	−0.1795 (3)	0.1177 (5)	0.45036 (18)	0.0469 (14)
N3	0.2360 (3)	0.3246 (5)	0.46982 (18)	0.0383 (12)
C1	0.0212 (3)	0.4257 (6)	0.4048 (2)	0.0312 (12)
C2	−0.0702 (3)	0.5859 (6)	0.3675 (2)	0.0408 (16)
C3	−0.1223 (4)	0.2676 (6)	0.4263 (2)	0.0348 (12)
C4	0.1463 (4)	0.4379 (6)	0.4141 (2)	0.0322 (12)
C5	0.1617 (4)	0.5785 (7)	0.3553 (3)	0.0372 (14)
C6	0.2126 (4)	0.9446 (7)	0.3265 (3)	0.0620 (19)
C7	0.4506 (3)	0.2847 (6)	0.5423 (2)	0.0422 (14)
C8	0.4774 (4)	0.4681 (7)	0.6026 (3)	0.0426 (16)
C9	0.6022 (5)	0.5459 (9)	0.7365 (3)	0.082 (2)
H2	−0.06294	0.71649	0.34245	0.0490*
H2A	−0.14022	−0.00431	0.47613	0.0560*
H2B	−0.25559	0.14364	0.44005	0.0560*
H6A	0.24631	1.09153	0.35108	0.0935*
H6B	0.12955	0.96701	0.28279	0.0935*
H6C	0.26633	0.87853	0.30921	0.0935*
H7A	0.52605	0.25699	0.53910	0.0503*
H7B	0.42814	0.14045	0.55766	0.0503*
H9A	0.65920	0.46760	0.78391	0.1228*
H9B	0.53185	0.60529	0.73993	0.1228*
H9C	0.64524	0.67231	0.72808	0.1228*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0355 (6)	0.0453 (6)	0.0495 (8)	0.0083 (5)	0.0206 (6)	0.0116 (5)
O1	0.074 (2)	0.0389 (17)	0.047 (2)	−0.0059 (15)	0.0348 (18)	0.0026 (14)
O2	0.094 (3)	0.0595 (19)	0.043 (2)	−0.0171 (18)	0.0411 (19)	−0.0062 (16)
O3	0.0295 (16)	0.0579 (18)	0.0405 (18)	−0.0004 (13)	0.0175 (14)	0.0102 (14)
O4	0.057 (2)	0.061 (2)	0.045 (2)	0.0107 (16)	0.0098 (18)	0.0004 (16)
O5	0.052 (2)	0.0447 (19)	0.069 (2)	0.0084 (15)	0.0254 (18)	0.0027 (15)
N1	0.033 (2)	0.0328 (18)	0.039 (2)	0.0001 (15)	0.0176 (18)	0.0045 (15)
N2	0.034 (2)	0.046 (2)	0.062 (3)	0.0034 (16)	0.025 (2)	0.0216 (18)
N3	0.031 (2)	0.047 (2)	0.040 (2)	−0.0043 (16)	0.0200 (19)	0.0012 (17)
C1	0.031 (2)	0.035 (2)	0.027 (2)	0.0002 (18)	0.014 (2)	0.0013 (17)
C2	0.044 (3)	0.041 (2)	0.039 (3)	0.005 (2)	0.022 (2)	0.0073 (19)
C3	0.031 (2)	0.035 (2)	0.031 (2)	0.0007 (19)	0.010 (2)	0.0015 (17)
C4	0.034 (2)	0.034 (2)	0.030 (2)	0.0019 (18)	0.017 (2)	0.0007 (18)
C5	0.035 (2)	0.037 (2)	0.040 (3)	−0.0008 (19)	0.019 (2)	0.000 (2)
C6	0.092 (4)	0.042 (3)	0.064 (3)	0.002 (2)	0.048 (3)	0.017 (2)
C7	0.028 (2)	0.044 (2)	0.046 (3)	0.0050 (19)	0.012 (2)	0.010 (2)
C8	0.028 (2)	0.049 (3)	0.051 (3)	−0.001 (2)	0.020 (2)	0.004 (2)
C9	0.084 (4)	0.096 (4)	0.045 (3)	0.004 (3)	0.017 (3)	−0.019 (3)

Geometric parameters (Å, º) top

S1—C2	1.710 (4)	N2—H2B	0.8600
S1—C3	1.748 (4)	C1—C2	1.349 (5)
O1—C5	1.318 (5)	C1—C4	1.449 (7)
O1—C6	1.451 (6)	C4—C5	1.509 (6)
O2—C5	1.184 (6)	C7—C8	1.505 (6)
O3—N3	1.431 (5)	C2—H2	0.9300
O3—C7	1.413 (4)	C6—H6A	0.9600
O4—C8	1.327 (6)	C6—H6B	0.9600
O4—C9	1.443 (6)	C6—H6C	0.9600
O5—C8	1.189 (5)	C7—H7A	0.9700
N1—C1	1.390 (5)	C7—H7B	0.9700
N1—C3	1.303 (7)	C9—H9A	0.9600
N2—C3	1.341 (6)	C9—H9B	0.9600
N3—C4	1.281 (5)	C9—H9C	0.9600
N2—H2A	0.8600

S1···N1	2.583 (4)	N1···H2A^vii	2.2200
S1···O5ⁱ	3.446 (4)	N2···H9A^viii	2.9300
S1···N3ⁱ	3.486 (4)	N3···H6Aⁱⁱⁱ	2.7700
S1···C8ⁱ	3.649 (6)	N3···H2A^vii	2.6800
S1···C9ⁱⁱ	3.605 (5)	C1···C3ⁱ	3.430 (5)
S1···H9Cⁱⁱ	3.1100	C2···C6^v	3.443 (6)
O1···O3	3.054 (4)	C3···C1ⁱ	3.430 (5)
O1···N3	3.111 (4)	C6···O3^vi	3.408 (5)
O2···N3	3.257 (4)	C6···O4^iv	3.385 (6)
O2···C6ⁱⁱⁱ	3.337 (5)	C6···O2^vi	3.337 (5)
O3···C6ⁱⁱⁱ	3.408 (5)	C6···C2^ix	3.443 (6)
O3···C8^iv	3.231 (6)	C7···C7^iv	3.530 (5)
O3···C7^iv	3.284 (5)	C7···O3^iv	3.284 (5)
O3···O5	2.747 (4)	C8···O3^iv	3.231 (6)
O3···O1	3.054 (4)	C8···S1ⁱ	3.649 (6)
O4···C6^iv	3.385 (6)	C9···S1^x	3.605 (5)
O5···S1ⁱ	3.446 (4)	C2···H6B^v	2.7800
O5···N3	3.100 (4)	C3···H9A^viii	3.0700
O5···N2ⁱ	3.097 (5)	C4···H6Aⁱⁱⁱ	2.9300
O5···O3	2.747 (4)	C5···H6Aⁱⁱⁱ	3.0000
O1···H7A^iv	2.8500	C5···H2	2.7500
O2···H6B	2.6600	H2···C5	2.7500
O2···H6Aⁱⁱⁱ	2.7000	H2···O2^ix	2.9100
O2···H6C	2.6000	H2A···N1^vii	2.2200
O2···H2^v	2.9100	H2A···N3^vii	2.6800
O2···H6B^v	2.8100	H2B···O5ⁱ	2.2700
O3···H7A^iv	2.7400	H6A···O2^vi	2.7000
O3···H6Aⁱⁱⁱ	2.5300	H6A···O3^vi	2.5300
O4···H6C^iv	2.5100	H6A···N3^vi	2.7700
O5···H9C	2.6500	H6A···C4^vi	2.9300
O5···H7B^vi	2.8300	H6A···C5^vi	3.0000
O5···H9B	2.6100	H6B···O2	2.6600
O5···H2Bⁱ	2.2700	H6B···O2^ix	2.8100
O5···H7A^iv	2.8800	H6B···C2^ix	2.7800
N1···S1	2.583 (4)	H6C···O2	2.6000
N1···N3	2.768 (6)	H6C···O4^iv	2.5100
N1···N2^vii	3.057 (5)	H7A···O1^iv	2.8500
N2···N3^vii	3.250 (5)	H7A···O3^iv	2.7400
N2···O5ⁱ	3.097 (5)	H7A···O5^iv	2.8800
N2···N1^vii	3.057 (5)	H7B···O5ⁱⁱⁱ	2.8300
N3···O5	3.100 (4)	H9A···N2^xi	2.9300
N3···N2^vii	3.250 (5)	H9A···C3^xi	3.0700
N3···O1	3.111 (4)	H9B···O5	2.6100
N3···O2	3.257 (4)	H9C···O5	2.6500
N3···S1ⁱ	3.486 (4)	H9C···S1^x	3.1100
N3···N1	2.768 (6)

C2—S1—C3	88.9 (2)	O4—C8—O5	124.3 (4)
C5—O1—C6	115.8 (3)	O4—C8—C7	109.5 (3)
N3—O3—C7	107.2 (3)	O5—C8—C7	126.2 (4)
C8—O4—C9	116.6 (4)	S1—C2—H2	125.00
C1—N1—C3	109.6 (3)	C1—C2—H2	125.00
O3—N3—C4	110.6 (3)	O1—C6—H6A	109.00
C3—N2—H2B	120.00	O1—C6—H6B	109.00
H2A—N2—H2B	120.00	O1—C6—H6C	109.00
C3—N2—H2A	120.00	H6A—C6—H6B	109.00
N1—C1—C2	116.2 (4)	H6A—C6—H6C	110.00
N1—C1—C4	119.0 (3)	H6B—C6—H6C	109.00
C2—C1—C4	124.7 (3)	O3—C7—H7A	109.00
S1—C2—C1	110.4 (3)	O3—C7—H7B	109.00
N1—C3—N2	124.4 (3)	C8—C7—H7A	109.00
S1—C3—N2	120.7 (4)	C8—C7—H7B	109.00
S1—C3—N1	114.9 (3)	H7A—C7—H7B	108.00
N3—C4—C1	118.7 (4)	O4—C9—H9A	109.00
N3—C4—C5	123.9 (5)	O4—C9—H9B	109.00
C1—C4—C5	117.4 (4)	O4—C9—H9C	109.00
O2—C5—C4	122.8 (4)	H9A—C9—H9B	110.00
O1—C5—O2	125.6 (4)	H9A—C9—H9C	110.00
O1—C5—C4	111.6 (4)	H9B—C9—H9C	109.00
O3—C7—C8	111.1 (3)

C3—S1—C2—C1	−0.1 (3)	O3—N3—C4—C5	0.9 (5)
C2—S1—C3—N1	0.4 (3)	N1—C1—C2—S1	−0.3 (4)
C2—S1—C3—N2	−178.8 (3)	C4—C1—C2—S1	−177.4 (3)
C6—O1—C5—O2	4.4 (8)	N1—C1—C4—N3	−19.6 (5)
C6—O1—C5—C4	−174.3 (4)	N1—C1—C4—C5	158.5 (3)
C7—O3—N3—C4	163.2 (3)	C2—C1—C4—N3	157.4 (4)
N3—O3—C7—C8	−76.2 (4)	C2—C1—C4—C5	−24.5 (5)
C9—O4—C8—O5	−4.5 (8)	N3—C4—C5—O1	−83.5 (5)
C9—O4—C8—C7	174.4 (4)	N3—C4—C5—O2	97.7 (6)
C3—N1—C1—C2	0.6 (4)	C1—C4—C5—O1	98.6 (5)
C3—N1—C1—C4	177.8 (3)	C1—C4—C5—O2	−80.2 (6)
C1—N1—C3—S1	−0.6 (4)	O3—C7—C8—O4	170.8 (4)
C1—N1—C3—N2	178.6 (3)	O3—C7—C8—O5	−10.3 (7)
O3—N3—C4—C1	178.8 (3)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, −y+3/2, z−1/2; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x, y−1/2, −z+1/2; (vi) x, y+1, z; (vii) −x, −y, −z+1; (viii) x−1, −y+1/2, z−1/2; (ix) −x, y+1/2, −z+1/2; (x) x+1, −y+3/2, z+1/2; (xi) x+1, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1^vii	0.86	2.22	3.057 (5)	163
N2—H2B···O5ⁱ	0.86	2.27	3.097 (5)	160
C6—H6A···O3^vi	0.96	2.53	3.408 (5)	152
C6—H6C···O4^iv	0.96	2.51	3.385 (6)	152

Symmetry codes: (i) −x, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₉H₁₁N₃O₅S
M_r	273.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.240 (2), 5.7500 (8), 19.887 (3)
β (°)	120.016 (8)
V (Å³)	1211.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.22 × 0.08 × 0.06

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	10459, 2168, 1102
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.124, 1.01
No. of reflections	2168
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1ⁱ	0.86	2.22	3.057 (5)	163
N2—H2B···O5ⁱⁱ	0.86	2.27	3.097 (5)	160
C6—H6A···O3ⁱⁱⁱ	0.96	2.53	3.408 (5)	152
C6—H6C···O4^iv	0.96	2.51	3.385 (6)	152

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science 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). SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cheng, X.-W. (2007). Acta Cryst. E63, o3728. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Fu, D. C., Chu, F. M. & Guo, Z. R. (2005). Chin. Chem. Lett. 16, 1305–1308. CAS Google Scholar
Saprykina, V. A., Vinogradova, V. I., Ambartsumova, R. F., Ibragimov, T. F. & Shakhidoyatov, Kh. M. (2006). Chem. Nat. Compd (USSR), 42, 4470–4472. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 4| April 2009| Page o713

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

Methyl 2-(2-amino-1,3-thia­zol-4-yl)-2-[(Z)-meth­oxy­carbonyl­meth­oxy­imino]ethano­ate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl 2-(2-amino-1,3-thiazol-4-yl)-2-[(Z)-methoxycarbonylmethoxyimino]ethanoate