Methyl 5-[N,N-bis­(methoxy­carbonyl­meth­yl)amino]-4-cyano-2-methoxy­carbonyl-3-thio­phene­ethan­o­ate

Wang, Q.; Li, Z.-S.; Sun, B.-W.

doi:10.1107/S1600536808028699

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1927

doi:10.1107/S1600536808028699

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Methyl 5-[N,N-bis(methoxycarbonylmethyl)amino]-4-cyano-2-methoxycarbonyl-3-thiopheneethanoate

Qiang Wang,^a Zhong-Shu Li ^a and Bai-Wang Sun ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 19 August 2008; accepted 8 September 2008; online 13 September 2008)

In the title compound, C₁₆H₁₈N₂O₈S, derived from ranelic acid, there is a highly substituted thiophene ring. The crystal structure involves intermolecular C—H⋯O and C—H⋯S hydrogen bonds.

Related literature

For related literature, see: Bonnelye et al. (2008 ); Fonseca (2008 ).

Experimental

Crystal data

C₁₆H₁₈N₂O₈S
M_r = 398.38
Triclinic, $[P \overline 1]$
a = 9.7164 (19) Å
b = 9.790 (2) Å
c = 10.170 (2) Å
α = 98.05 (3)°
β = 96.71 (3)°
γ = 95.81 (3)°
V = 944.5 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 293 (2) K
0.25 × 0.20 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.942, T_max = 0.988
9976 measured reflections
4313 independent reflections
3561 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.03
4313 reflections
246 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 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
C3—H3A⋯O3ⁱ	0.97	2.51	3.355 (3)	146
C16—H16A⋯O5ⁱⁱ	0.96	2.57	3.421 (3)	148
C16—H16C⋯Sⁱⁱ	0.96	2.87	3.727 (3)	149
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+1, -y+1, -z.

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808028699/sg2258sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028699/sg2258Isup2.hkl

checkCIF report

Comment top

The title compound, (I), C₁₆H₁₈O₈N₂S, is an important intermediate in the synthesis of strontium ranelate, a medicine for the treatment of osteoporosis (Bonnelye et al., 2008; Fonseca, 2008). Strontium ranelate is composed of two stable strontium ions combined with the anion of organic ranelic acid. The ranelic acid is a carrier that makes the treatment palatable, and the strontium is the active component with regard to the bone. We report here the crystal structure of the title compound. The molecular structure of (I) is shown in Fig. 1 and geometric parameters are given in Table 1. In the crystal (Fig. 2 and Table 2), there are intermolecular C—H···O and C—H···S hydrogen bonds leading to a one-dimensional structure.

Related literature top

For related literature, see: Bonnelye et al. (2008); Fonseca (2008).

Experimental top

All chemicals used (reagent grade) were commercially available. Methyl 5-[bis(methoxycarbonylmethyl)amino]-4-cyano-3-(methoxycarbonyl)-2-thiophene- carboxylate (0.426 g, 0.1 mmol) was added to a solution containing ethanol (8 ml) and acetone (4 ml). The mixture was stirred at room temperature for 10 min and then filtered off. Colorless crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature over several days.

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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Crystal packing of the compound (I) viewed along the b axis. Hydrogen bonds are shown as dashed lines.

methyl 5-[N,N-bis(methoxycarbonylmethyl)amino]-4-cyano-2- methoxycarbonyl-3-thiophene-ethanoate top

Crystal data top

C₁₆H₁₈N₂O₈S	Z = 2
M_r = 398.38	F(000) = 416
Triclinic, P1	D_x = 1.401 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7164 (19) Å	Cell parameters from 6733 reflections
b = 9.790 (2) Å	θ = 3.3–27.3°
c = 10.170 (2) Å	µ = 0.22 mm⁻¹
α = 98.05 (3)°	T = 293 K
β = 96.71 (3)°	Prism, colorless
γ = 95.81 (3)°	0.25 × 0.20 × 0.18 mm
V = 944.5 (3) Å³

Data collection top

Rigaku SCXmini diffractometer	4313 independent reflections
Radiation source: fine-focus sealed tube	3561 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8.192 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.942, T_max = 0.988	l = −13→13
9976 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.062P)² + 0.411P] where P = (F_o² + 2F_c²)/3
4313 reflections	(Δ/σ)_max < 0.001
246 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O₈S	γ = 95.81 (3)°
M_r = 398.38	V = 944.5 (3) Å³
Triclinic, P1	Z = 2
a = 9.7164 (19) Å	Mo Kα radiation
b = 9.790 (2) Å	µ = 0.22 mm⁻¹
c = 10.170 (2) Å	T = 293 K
α = 98.05 (3)°	0.25 × 0.20 × 0.18 mm
β = 96.71 (3)°

Data collection top

Rigaku SCXmini diffractometer	4313 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	3561 reflections with I > 2σ(I)
T_min = 0.942, T_max = 0.988	R_int = 0.027
9976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.33 e Å⁻³
4313 reflections	Δρ_min = −0.38 e Å⁻³
246 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
C1	0.0925 (5)	0.8277 (4)	0.4871 (3)	0.0967 (13)
H1A	0.165 (3)	0.894 (3)	0.4933 (6)	0.145*
H1B	0.116 (3)	0.7635 (17)	0.5387 (14)	0.145*
H1C	0.018 (2)	0.866 (3)	0.5154 (12)	0.145*
C2	0.0887 (2)	0.8372 (2)	0.2560 (2)	0.0414 (5)
C3	0.03705 (19)	0.7542 (2)	0.11943 (19)	0.0374 (4)
H3A	0.0661	0.6620	0.1164	0.045*
H3B	−0.0642	0.7441	0.1059	0.045*
C4	−0.01502 (19)	0.8243 (2)	−0.1025 (2)	0.0366 (4)
H4A	0.0231	0.8874	−0.1582	0.044*
H4B	−0.0962	0.8606	−0.0702	0.044*
C5	−0.0589 (2)	0.6829 (2)	−0.1857 (2)	0.0427 (5)
C6	−0.2176 (5)	0.5578 (4)	−0.3673 (4)	0.1086 (14)
H6A	−0.2891	0.5740	−0.4348	0.163*
H6B	−0.2567	0.4957	−0.3126	0.163*
H6C	−0.1448	0.5171	−0.4094	0.163*
C7	0.22416 (18)	0.80692 (18)	−0.00849 (18)	0.0312 (4)
C8	0.30195 (18)	0.86329 (19)	−0.09923 (18)	0.0321 (4)
C9	0.2567 (2)	0.9617 (2)	−0.18082 (19)	0.0369 (4)
C10	0.43987 (18)	0.82416 (19)	−0.09451 (18)	0.0335 (4)
C11	0.5374 (2)	0.8694 (2)	−0.18941 (19)	0.0404 (4)
H11A	0.5404	0.9690	−0.1876	0.048*
H11B	0.6307	0.8498	−0.1592	0.048*
C12	0.4935 (2)	0.7974 (2)	−0.3310 (2)	0.0446 (5)
C13	0.5241 (4)	0.8027 (4)	−0.5571 (3)	0.0940 (11)
H13A	0.5736	0.8606	−0.6092	0.141*
H13B	0.4257	0.7956	−0.5864	0.141*
H13C	0.5541	0.7119	−0.5686	0.141*
C14	0.46807 (18)	0.7442 (2)	0.00257 (18)	0.0335 (4)
C15	0.59750 (19)	0.6869 (2)	0.04245 (19)	0.0360 (4)
C16	0.7100 (2)	0.5700 (2)	0.2060 (2)	0.0501 (5)
H16A	0.6891	0.5245	0.2802	0.075*
H16B	0.7815	0.6466	0.2366	0.075*
H16C	0.7418	0.5053	0.1396	0.075*
O1	0.0564 (2)	0.76176 (18)	0.34904 (16)	0.0637 (5)
O2	0.1471 (2)	0.95261 (18)	0.27677 (18)	0.0673 (5)
O3	−0.0096 (2)	0.57999 (18)	−0.1647 (2)	0.0719 (6)
O4	−0.15997 (19)	0.68911 (18)	−0.28405 (17)	0.0626 (5)
O5	0.4141 (3)	0.6943 (2)	−0.3638 (2)	0.1020 (9)
O6	0.5525 (2)	0.8633 (2)	−0.41698 (17)	0.0695 (5)
O7	0.70142 (14)	0.69773 (18)	−0.01103 (16)	0.0520 (4)
O8	0.58547 (14)	0.62078 (16)	0.14789 (15)	0.0438 (3)
N1	0.08891 (15)	0.81812 (17)	0.01103 (16)	0.0346 (3)
N2	0.2253 (2)	1.0438 (2)	−0.2444 (2)	0.0535 (5)
S	0.32536 (5)	0.71175 (5)	0.08736 (5)	0.03457 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.151 (4)	0.103 (3)	0.0364 (14)	0.029 (2)	0.0078 (17)	0.0058 (15)
C2	0.0371 (10)	0.0491 (12)	0.0399 (11)	0.0130 (9)	0.0055 (8)	0.0071 (9)
C3	0.0266 (9)	0.0471 (11)	0.0394 (10)	0.0020 (7)	0.0078 (7)	0.0087 (8)
C4	0.0280 (9)	0.0392 (10)	0.0447 (11)	0.0078 (7)	0.0016 (8)	0.0136 (8)
C5	0.0412 (11)	0.0444 (11)	0.0418 (11)	0.0083 (9)	−0.0004 (8)	0.0071 (9)
C6	0.132 (3)	0.080 (2)	0.088 (2)	0.010 (2)	−0.054 (2)	−0.0192 (19)
C7	0.0275 (8)	0.0346 (9)	0.0308 (9)	0.0026 (7)	0.0019 (7)	0.0052 (7)
C8	0.0301 (9)	0.0364 (9)	0.0297 (9)	0.0015 (7)	0.0031 (7)	0.0069 (7)
C9	0.0335 (9)	0.0429 (10)	0.0348 (10)	0.0016 (8)	0.0064 (7)	0.0084 (8)
C10	0.0292 (9)	0.0388 (10)	0.0312 (9)	−0.0010 (7)	0.0047 (7)	0.0039 (8)
C11	0.0329 (10)	0.0530 (12)	0.0366 (10)	−0.0014 (8)	0.0081 (8)	0.0128 (9)
C12	0.0494 (12)	0.0491 (12)	0.0391 (11)	0.0046 (10)	0.0171 (9)	0.0112 (9)
C13	0.137 (3)	0.106 (3)	0.0417 (15)	−0.002 (2)	0.0369 (17)	0.0125 (16)
C14	0.0259 (8)	0.0432 (10)	0.0318 (9)	0.0027 (7)	0.0055 (7)	0.0068 (8)
C15	0.0280 (9)	0.0429 (10)	0.0358 (10)	0.0015 (7)	0.0030 (7)	0.0045 (8)
C16	0.0396 (11)	0.0547 (13)	0.0573 (13)	0.0102 (9)	−0.0046 (10)	0.0188 (11)
O1	0.0920 (13)	0.0632 (11)	0.0376 (8)	0.0077 (9)	0.0124 (8)	0.0119 (8)
O2	0.0858 (13)	0.0538 (10)	0.0547 (10)	−0.0060 (9)	−0.0015 (9)	0.0011 (8)
O3	0.0808 (13)	0.0454 (9)	0.0806 (13)	0.0218 (9)	−0.0235 (10)	−0.0024 (9)
O4	0.0680 (11)	0.0608 (10)	0.0513 (10)	0.0112 (8)	−0.0206 (8)	0.0029 (8)
O5	0.161 (2)	0.0805 (14)	0.0505 (11)	−0.0555 (15)	0.0369 (13)	−0.0065 (10)
O6	0.0858 (13)	0.0810 (12)	0.0413 (9)	−0.0148 (10)	0.0204 (9)	0.0163 (9)
O7	0.0305 (7)	0.0792 (11)	0.0519 (9)	0.0127 (7)	0.0118 (6)	0.0202 (8)
O8	0.0322 (7)	0.0563 (9)	0.0478 (8)	0.0104 (6)	0.0060 (6)	0.0207 (7)
N1	0.0255 (7)	0.0430 (9)	0.0366 (8)	0.0047 (6)	0.0049 (6)	0.0094 (7)
N2	0.0579 (12)	0.0532 (11)	0.0536 (11)	0.0069 (9)	0.0061 (9)	0.0237 (9)
S	0.0279 (2)	0.0437 (3)	0.0358 (3)	0.00654 (18)	0.00741 (17)	0.0147 (2)

Geometric parameters (Å, º) top

C1—O1	1.448 (3)	C8—C9	1.427 (3)
C1—H1A	0.9033	C8—C10	1.428 (3)
C1—H1B	0.9033	C9—N2	1.143 (3)
C1—H1C	0.9033	C10—C14	1.363 (3)
C2—O2	1.191 (3)	C10—C11	1.508 (3)
C2—O1	1.325 (3)	C11—C12	1.504 (3)
C2—C3	1.510 (3)	C11—H11A	0.9700
C3—N1	1.456 (2)	C11—H11B	0.9700
C3—H3A	0.9700	C12—O5	1.189 (3)
C3—H3B	0.9700	C12—O6	1.308 (3)
C4—N1	1.455 (2)	C13—O6	1.448 (3)
C4—C5	1.511 (3)	C13—H13A	0.9600
C4—H4A	0.9700	C13—H13B	0.9600
C4—H4B	0.9700	C13—H13C	0.9600
C5—O3	1.193 (3)	C14—C15	1.466 (3)
C5—O4	1.330 (2)	C14—S	1.7420 (18)
C6—O4	1.457 (3)	C15—O7	1.204 (2)
C6—H6A	0.9600	C15—O8	1.338 (2)
C6—H6B	0.9600	C16—O8	1.448 (2)
C6—H6C	0.9600	C16—H16A	0.9600
C7—N1	1.365 (2)	C16—H16B	0.9600
C7—C8	1.396 (2)	C16—H16C	0.9600
C7—S	1.7323 (19)

O1—C1—H1A	109.5	C14—C10—C11	126.48 (17)
O1—C1—H1B	109.5	C8—C10—C11	121.39 (17)
H1A—C1—H1B	109.5	C12—C11—C10	112.45 (16)
O1—C1—H1C	109.5	C12—C11—H11A	109.1
H1A—C1—H1C	109.5	C10—C11—H11A	109.1
H1B—C1—H1C	109.5	C12—C11—H11B	109.1
O2—C2—O1	125.5 (2)	C10—C11—H11B	109.1
O2—C2—C3	125.5 (2)	H11A—C11—H11B	107.8
O1—C2—C3	108.99 (18)	O5—C12—O6	122.9 (2)
N1—C3—C2	112.93 (16)	O5—C12—C11	125.5 (2)
N1—C3—H3A	109.0	O6—C12—C11	111.64 (19)
C2—C3—H3A	109.0	O6—C13—H13A	109.5
N1—C3—H3B	109.0	O6—C13—H13B	109.5
C2—C3—H3B	109.0	H13A—C13—H13B	109.5
H3A—C3—H3B	107.8	O6—C13—H13C	109.5
N1—C4—C5	111.64 (16)	H13A—C13—H13C	109.5
N1—C4—H4A	109.3	H13B—C13—H13C	109.5
C5—C4—H4A	109.3	C10—C14—C15	129.21 (17)
N1—C4—H4B	109.3	C10—C14—S	112.01 (14)
C5—C4—H4B	109.3	C15—C14—S	118.78 (14)
H4A—C4—H4B	108.0	O7—C15—O8	124.03 (18)
O3—C5—O4	125.0 (2)	O7—C15—C14	125.19 (18)
O3—C5—C4	124.21 (19)	O8—C15—C14	110.78 (16)
O4—C5—C4	110.76 (17)	O8—C16—H16A	109.5
O4—C6—H6A	109.5	O8—C16—H16B	109.5
O4—C6—H6B	109.5	H16A—C16—H16B	109.5
H6A—C6—H6B	109.5	O8—C16—H16C	109.5
O4—C6—H6C	109.5	H16A—C16—H16C	109.5
H6A—C6—H6C	109.5	H16B—C16—H16C	109.5
H6B—C6—H6C	109.5	C2—O1—C1	116.7 (2)
N1—C7—C8	129.48 (17)	C5—O4—C6	116.3 (2)
N1—C7—S	120.44 (14)	C12—O6—C13	117.7 (2)
C8—C7—S	110.07 (13)	C15—O8—C16	116.74 (16)
C7—C8—C9	124.59 (17)	C7—N1—C4	119.77 (16)
C7—C8—C10	113.62 (16)	C7—N1—C3	117.45 (15)
C9—C8—C10	121.51 (16)	C4—N1—C3	115.49 (15)
N2—C9—C8	177.3 (2)	C7—S—C14	92.11 (9)
C14—C10—C8	112.12 (16)

O2—C2—C3—N1	11.3 (3)	S—C14—C15—O7	177.27 (17)
O1—C2—C3—N1	−169.76 (17)	C10—C14—C15—O8	176.21 (19)
N1—C4—C5—O3	−3.4 (3)	S—C14—C15—O8	−3.1 (2)
N1—C4—C5—O4	176.17 (17)	O2—C2—O1—C1	1.7 (4)
N1—C7—C8—C9	8.5 (3)	C3—C2—O1—C1	−177.2 (2)
S—C7—C8—C9	−171.41 (15)	O3—C5—O4—C6	3.0 (4)
N1—C7—C8—C10	−177.50 (17)	C4—C5—O4—C6	−176.6 (3)
S—C7—C8—C10	2.6 (2)	O5—C12—O6—C13	−3.2 (4)
C7—C8—C9—N2	129 (5)	C11—C12—O6—C13	177.7 (2)
C10—C8—C9—N2	−45 (5)	O7—C15—O8—C16	5.2 (3)
C7—C8—C10—C14	−2.7 (2)	C14—C15—O8—C16	−174.41 (17)
C9—C8—C10—C14	171.57 (17)	C8—C7—N1—C4	34.7 (3)
C7—C8—C10—C11	177.14 (16)	S—C7—N1—C4	−145.47 (15)
C9—C8—C10—C11	−8.6 (3)	C8—C7—N1—C3	−176.48 (18)
C14—C10—C11—C12	109.2 (2)	S—C7—N1—C3	3.4 (2)
C8—C10—C11—C12	−70.6 (2)	C5—C4—N1—C7	76.6 (2)
C10—C11—C12—O5	−17.2 (4)	C5—C4—N1—C3	−72.8 (2)
C10—C11—C12—O6	161.94 (19)	C2—C3—N1—C7	76.1 (2)
C8—C10—C14—C15	−177.92 (18)	C2—C3—N1—C4	−133.71 (17)
C11—C10—C14—C15	2.3 (3)	N1—C7—S—C14	178.60 (15)
C8—C10—C14—S	1.4 (2)	C8—C7—S—C14	−1.50 (14)
C11—C10—C14—S	−178.35 (15)	C10—C14—S—C7	0.03 (15)
C10—C14—C15—O7	−3.4 (3)	C15—C14—S—C7	179.46 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.97	2.51	3.355 (3)	146
C16—H16A···O5ⁱⁱ	0.96	2.57	3.421 (3)	148
C16—H16C···Sⁱⁱ	0.96	2.87	3.727 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O₈S
M_r	398.38
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.7164 (19), 9.790 (2), 10.170 (2)
α, β, γ (°)	98.05 (3), 96.71 (3), 95.81 (3)
V (Å³)	944.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.25 × 0.20 × 0.18

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.942, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9976, 4313, 3561
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.03
No. of reflections	4313
No. of parameters	246
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.38

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O3ⁱ	0.97	2.51	3.355 (3)	146.2
C16—H16A···O5ⁱⁱ	0.96	2.57	3.421 (3)	148.4
C16—H16C···Sⁱⁱ	0.96	2.87	3.727 (3)	148.5

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

References

Bonnelye, E., Chabadel, A., Saltel, F. & Jurdic, P. (2008). Bone, 42, 129–138. Web of Science CrossRef PubMed CAS Google Scholar
Fonseca, J. E. (2008). Rheumatology, 47, iv17–iv19. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku. (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 10| October 2008| Page o1927

doi:10.1107/S1600536808028699

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

Methyl 5-[N,N-bis­­(meth­oxy­carbonyl­meth­yl)amino]-4-cyano-2-meth­oxy­carbonyl-3-thio­phene­ethan­o­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

Methyl 5-[N,N-bis(methoxycarbonylmethyl)amino]-4-cyano-2-methoxycarbonyl-3-thiopheneethanoate