Diethyl 2-methyl-6-(2-thia­zolidinyl)-4-(2-thienyl)-1,4-di­hydro­pyridine-3,5-di­carboxyl­ate

In the title compound, C₁₉H₂₄N₂O₄S₂, the substituted 1,4-di­hydro­pyridine ring has a flat-boat conformation. The two ethoxy­carbonyl groups are twisted in the same direction and the plane of the 2-thio­phene ring is almost perpendicular to the 1,4-di­hydro­pyridine ring.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.055
• wR factor = 0.125
• Data-to-parameter ratio = 21.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_360  Alert C Short  C(sp3)-C(sp3) Bond  C(25)  -   C(26)  =       1.37 Ang.

PLAT_420  Alert C D-H Without Acceptor       N(12)  -   H(12)             ?


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction Limited, 2002); cell refinement: CrysAlis RED (Oxford Diffraction Limited, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXS97.

Diethyl 2-methyl-6-(2-thiazolidinyl)-4-(2-thienyl-1,4-dihydropyridine- -3,5-dicarboxylate

Crystal data

C19H24N2O4S2	Z = 2
Mr = 408.52	F(000) = 432
Triclinic, P1	Dx = 1.327 Mg m^−3 Dm = 1.33 (1) Mg m^−3 Dm measured by flotation in bromoform–hexane
a = 8.9441 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.222 (2) Å	Cell parameters from 6596 reflections
c = 11.489 (2) Å	θ = 12.4–28.6°
α = 69.21 (3)°	µ = 0.29 mm^−1
β = 71.47 (3)°	T = 293 K
γ = 83.99 (3)°	Prism, yellow
V = 1022.0 (4) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur CCD diffractometer	2163 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
Graphite monochromator	θmax = 29.1°, θmin = 3.1°
Detector resolution: Sapphire CCD detector pixels mm^-1	h = −10→12
Rotation method data acquisition using ω and φ scans	k = −15→15
6596 measured reflections	l = −15→15
5344 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters constrained
S = 0.96	w = 1/[σ^2(Fo^2) + (0.0448P)^2] where P = (Fo^2 + 2Fc^2)/3
5344 reflections	(Δ/σ)max = 0.022
247 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.48 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C2	−0.1335 (3)	0.9317 (2)	0.3083 (2)	0.0367 (6)
C3	−0.2244 (3)	0.8259 (2)	0.3711 (2)	0.0379 (6)
C4	−0.2930 (3)	0.7845 (2)	0.5185 (2)	0.0398 (6)
H4	−0.3911	0.7370	0.5447	0.048*
C5	−0.3315 (3)	0.9016 (3)	0.5607 (2)	0.0422 (6)
C6	−0.2438 (3)	1.0082 (3)	0.4903 (2)	0.0441 (6)
C7	−0.0330 (3)	0.9783 (2)	0.1664 (2)	0.0408 (6)
H7	−0.0990	0.9818	0.1116	0.049*
C9	0.2790 (3)	0.9854 (3)	0.0806 (3)	0.0668 (9)
H9A	0.3675	0.9523	0.1138	0.080*
H9B	0.3168	1.0165	−0.0141	0.080*
C10	0.1990 (3)	1.0904 (3)	0.1308 (3)	0.0629 (8)
H10A	0.1984	1.0705	0.2203	0.075*
H10B	0.2557	1.1702	0.0780	0.075*
N12	0.0379 (2)	1.1018 (2)	0.1242 (2)	0.0491 (6)
H12	−0.0087	1.1730	0.0985	0.059*
C12	−0.2550 (3)	0.7519 (2)	0.2986 (3)	0.0421 (6)
C15	−0.4147 (4)	0.5874 (3)	0.3114 (3)	0.0707 (9)
H15A	−0.4452	0.5019	0.3722	0.085*
H15B	−0.3272	0.5809	0.2381	0.085*
C16	−0.5468 (5)	0.6487 (5)	0.2655 (5)	0.1402 (19)
H16A	−0.6351	0.6511	0.3387	0.210*
H16B	−0.5752	0.6013	0.2205	0.210*
H16C	−0.5173	0.7340	0.2071	0.210*
C17	−0.1777 (3)	0.6962 (2)	0.5818 (2)	0.0440 (6)
C19	−0.0438 (4)	0.5525 (3)	0.7357 (3)	0.0795 (10)
H19	−0.0115	0.5013	0.8070	0.095*
C20	0.0384 (4)	0.5704 (3)	0.6137 (4)	0.0764 (10)
H20	0.1355	0.5329	0.5887	0.092*
C21	−0.0373 (4)	0.6537 (3)	0.5237 (3)	0.0660 (9)
H21	0.0059	0.6765	0.4336	0.079*
C22	−0.4587 (3)	0.8939 (3)	0.6815 (3)	0.0526 (7)
C25	−0.6520 (4)	0.7560 (4)	0.8586 (3)	0.0933 (12)
H25B	−0.6032	0.7629	0.9204	0.112*
H25A	−0.7340	0.8196	0.8519	0.112*
C26	−0.7172 (7)	0.6374 (5)	0.9031 (5)	0.194 (3)
H26A	−0.7344	0.6205	0.8321	0.291*
H26B	−0.8160	0.6334	0.9696	0.291*
H26C	−0.6470	0.5749	0.9389	0.291*
C27	−0.2552 (4)	1.1299 (3)	0.5182 (3)	0.0659 (9)
H27A	−0.3637	1.1463	0.5573	0.099*
H27B	−0.2131	1.1989	0.4381	0.099*
H27C	−0.1961	1.1227	0.5770	0.099*
N1	−0.1299 (2)	1.01246 (19)	0.37406 (19)	0.0453 (5)
H1	−0.0544	1.0674	0.3419	0.054*
O13	−0.1925 (2)	0.76672 (18)	0.18480 (17)	0.0598 (5)
O14	−0.3653 (2)	0.65982 (18)	0.37544 (17)	0.0584 (5)
O23	−0.4932 (2)	0.9723 (2)	0.73487 (19)	0.0730 (6)
O24	−0.5351 (2)	0.7802 (2)	0.73244 (18)	0.0661 (6)
S8	0.12942 (8)	0.86367 (7)	0.13985 (7)	0.0565 (2)
S18	−0.21617 (12)	0.63390 (10)	0.74823 (8)	0.0908 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C2	0.0378 (14)	0.0432 (15)	0.0329 (14)	0.0051 (12)	−0.0141 (11)	−0.0157 (12)
C3	0.0383 (14)	0.0451 (16)	0.0330 (13)	0.0022 (12)	−0.0102 (11)	−0.0175 (12)
C4	0.0424 (15)	0.0472 (16)	0.0322 (14)	−0.0006 (12)	−0.0104 (12)	−0.0168 (12)
C5	0.0446 (15)	0.0543 (17)	0.0328 (14)	0.0112 (13)	−0.0151 (12)	−0.0208 (13)
C6	0.0534 (17)	0.0487 (17)	0.0376 (15)	0.0085 (14)	−0.0186 (13)	−0.0215 (13)
C7	0.0459 (15)	0.0451 (16)	0.0325 (14)	0.0022 (13)	−0.0142 (12)	−0.0131 (12)
C9	0.0435 (17)	0.100 (3)	0.0513 (18)	−0.0014 (17)	−0.0121 (14)	−0.0201 (18)
C10	0.059 (2)	0.080 (2)	0.0523 (18)	−0.0177 (17)	−0.0180 (15)	−0.0195 (17)
N12	0.0534 (14)	0.0404 (14)	0.0505 (14)	0.0002 (11)	−0.0173 (11)	−0.0105 (11)
C12	0.0459 (16)	0.0434 (16)	0.0390 (16)	0.0024 (13)	−0.0149 (13)	−0.0151 (13)
C15	0.082 (2)	0.072 (2)	0.071 (2)	−0.0177 (19)	−0.0208 (18)	−0.0362 (18)
C16	0.121 (4)	0.154 (4)	0.232 (6)	0.042 (3)	−0.117 (4)	−0.121 (4)
C17	0.0531 (17)	0.0428 (16)	0.0374 (15)	−0.0022 (13)	−0.0150 (13)	−0.0132 (12)
C19	0.085 (3)	0.078 (2)	0.067 (2)	0.014 (2)	−0.042 (2)	−0.0010 (19)
C20	0.073 (2)	0.064 (2)	0.081 (3)	0.0168 (18)	−0.031 (2)	−0.0091 (19)
C21	0.062 (2)	0.075 (2)	0.0494 (18)	0.0161 (17)	−0.0181 (16)	−0.0108 (16)
C22	0.0483 (17)	0.073 (2)	0.0416 (17)	0.0139 (16)	−0.0197 (14)	−0.0243 (16)
C25	0.074 (2)	0.112 (3)	0.060 (2)	0.007 (2)	0.0210 (19)	−0.028 (2)
C26	0.227 (6)	0.111 (4)	0.128 (4)	−0.041 (4)	0.101 (4)	−0.029 (3)
C27	0.092 (2)	0.059 (2)	0.0544 (18)	0.0082 (17)	−0.0218 (17)	−0.0299 (16)
N1	0.0496 (13)	0.0504 (14)	0.0408 (13)	−0.0049 (11)	−0.0135 (11)	−0.0199 (11)
O13	0.0746 (14)	0.0695 (13)	0.0390 (11)	−0.0131 (11)	−0.0086 (10)	−0.0266 (10)
O14	0.0656 (13)	0.0666 (13)	0.0486 (11)	−0.0187 (11)	−0.0098 (10)	−0.0272 (10)
O23	0.0729 (14)	0.0963 (17)	0.0597 (13)	0.0193 (12)	−0.0115 (11)	−0.0508 (13)
O24	0.0567 (13)	0.0811 (16)	0.0441 (12)	0.0009 (11)	0.0087 (10)	−0.0234 (11)
S8	0.0508 (5)	0.0634 (5)	0.0457 (4)	0.0081 (4)	−0.0055 (3)	−0.0175 (4)
S18	0.1047 (8)	0.1102 (8)	0.0451 (5)	0.0306 (6)	−0.0278 (5)	−0.0158 (5)

Geometric parameters (Å, º)

C2—C3	1.346 (3)	C15—H15A	0.9700
C2—N1	1.379 (3)	C15—H15B	0.9700
C2—C7	1.517 (3)	C16—H16A	0.9600
C3—C12	1.463 (3)	C16—H16B	0.9600
C3—C4	1.517 (3)	C16—H16C	0.9600
C4—C17	1.524 (3)	C17—C21	1.349 (3)
C4—C5	1.527 (3)	C17—S18	1.717 (3)
C4—H4	0.9800	C19—C20	1.312 (4)
C5—C6	1.343 (4)	C19—S18	1.700 (3)
C5—C22	1.469 (4)	C19—H19	0.9300
C6—N1	1.387 (3)	C20—C21	1.424 (4)
C6—C27	1.497 (4)	C20—H20	0.9300
C7—N12	1.439 (3)	C21—H21	0.9300
C7—S8	1.861 (2)	C22—O23	1.205 (3)
C7—H7	0.9800	C22—O24	1.354 (3)
C9—C10	1.508 (4)	C25—C26	1.365 (5)
C9—S8	1.806 (3)	C25—O24	1.444 (3)
C9—H9A	0.9700	C25—H25B	0.9700
C9—H9B	0.9700	C25—H25A	0.9700
C10—N12	1.457 (3)	C26—H26A	0.9600
C10—H10A	0.9700	C26—H26B	0.9600
C10—H10B	0.9700	C26—H26C	0.9600
N12—H12	0.8600	C27—H27A	0.9600
C12—O13	1.204 (3)	C27—H27B	0.9600
C12—O14	1.354 (3)	C27—H27C	0.9600
C15—O14	1.449 (3)	N1—H1	0.8600
C15—C16	1.455 (5)
C3—C2—N1	119.4 (2)	H15A—C15—H15B	108.1
C3—C2—C7	127.3 (2)	C15—C16—H16A	109.5
N1—C2—C7	113.3 (2)	C15—C16—H16B	109.5
C2—C3—C12	120.6 (2)	H16A—C16—H16B	109.5
C2—C3—C4	118.6 (2)	C15—C16—H16C	109.5
C12—C3—C4	120.8 (2)	H16A—C16—H16C	109.5
C3—C4—C17	109.44 (19)	H16B—C16—H16C	109.5
C3—C4—C5	109.8 (2)	C21—C17—C4	128.7 (2)
C17—C4—C5	112.19 (19)	C21—C17—S18	109.4 (2)
C3—C4—H4	108.5	C4—C17—S18	121.89 (18)
C17—C4—H4	108.5	C20—C19—S18	112.0 (2)
C5—C4—H4	108.5	C20—C19—H19	124.0
C6—C5—C22	121.0 (2)	S18—C19—H19	124.0
C6—C5—C4	119.5 (2)	C19—C20—C21	112.6 (3)
C22—C5—C4	119.4 (2)	C19—C20—H20	123.7
C5—C6—N1	118.6 (2)	C21—C20—H20	123.7
C5—C6—C27	128.2 (2)	C17—C21—C20	113.5 (3)
N1—C6—C27	113.1 (2)	C17—C21—H21	123.2
N12—C7—C2	114.1 (2)	C20—C21—H21	123.2
N12—C7—S8	107.47 (17)	O23—C22—O24	121.8 (3)
C2—C7—S8	109.40 (16)	O23—C22—C5	127.6 (3)
N12—C7—H7	108.6	O24—C22—C5	110.6 (2)
C2—C7—H7	108.6	C26—C25—O24	110.8 (3)
S8—C7—H7	108.6	C26—C25—H25B	109.5
C10—C9—S8	105.29 (19)	O24—C25—H25B	109.5
C10—C9—H9A	110.7	C26—C25—H25A	109.5
S8—C9—H9A	110.7	O24—C25—H25A	109.5
C10—C9—H9B	110.7	H25B—C25—H25A	108.1
S8—C9—H9B	110.7	C25—C26—H26A	109.5
H9A—C9—H9B	108.8	C25—C26—H26B	109.5
N12—C10—C9	108.5 (2)	H26A—C26—H26B	109.5
N12—C10—H10A	110.0	C25—C26—H26C	109.5
C9—C10—H10A	110.0	H26A—C26—H26C	109.5
N12—C10—H10B	110.0	H26B—C26—H26C	109.5
C9—C10—H10B	110.0	C6—C27—H27A	109.5
H10A—C10—H10B	108.4	C6—C27—H27B	109.5
C7—N12—C10	111.0 (2)	H27A—C27—H27B	109.5
C7—N12—H12	124.5	C6—C27—H27C	109.5
C10—N12—H12	124.5	H27A—C27—H27C	109.5
O13—C12—O14	121.7 (2)	H27B—C27—H27C	109.5
O13—C12—C3	126.4 (2)	C2—N1—C6	122.3 (2)
O14—C12—C3	111.9 (2)	C2—N1—H1	118.9
O14—C15—C16	110.6 (3)	C6—N1—H1	118.9
O14—C15—H15A	109.5	C12—O14—C15	116.6 (2)
C16—C15—H15A	109.5	C22—O24—C25	115.6 (3)
O14—C15—H15B	109.5	C9—S8—C7	92.38 (13)
C16—C15—H15B	109.5	C19—S18—C17	92.42 (15)
N1—C2—C3—C12	168.0 (2)	C3—C4—C17—C21	−2.0 (4)
C7—C2—C3—C12	−9.9 (4)	C5—C4—C17—C21	−124.1 (3)
N1—C2—C3—C4	−12.6 (3)	C3—C4—C17—S18	178.65 (18)
C7—C2—C3—C4	169.4 (2)	C5—C4—C17—S18	56.6 (3)
C2—C3—C4—C17	−89.3 (3)	S18—C19—C20—C21	0.3 (4)
C12—C3—C4—C17	90.1 (3)	C4—C17—C21—C20	−179.1 (3)
C2—C3—C4—C5	34.2 (3)	S18—C17—C21—C20	0.3 (3)
C12—C3—C4—C5	−146.4 (2)	C19—C20—C21—C17	−0.4 (4)
C3—C4—C5—C6	−31.0 (3)	C6—C5—C22—O23	−4.9 (4)
C17—C4—C5—C6	90.9 (3)	C4—C5—C22—O23	171.9 (3)
C3—C4—C5—C22	152.1 (2)	C6—C5—C22—O24	177.3 (2)
C17—C4—C5—C22	−86.0 (3)	C4—C5—C22—O24	−5.9 (3)
C22—C5—C6—N1	−177.1 (2)	C3—C2—N1—C6	−16.7 (3)
C4—C5—C6—N1	6.0 (3)	C7—C2—N1—C6	161.5 (2)
C22—C5—C6—C27	0.6 (4)	C5—C6—N1—C2	20.1 (3)
C4—C5—C6—C27	−176.2 (2)	C27—C6—N1—C2	−158.0 (2)
C3—C2—C7—N12	173.7 (2)	O13—C12—O14—C15	−5.3 (4)
N1—C2—C7—N12	−4.4 (3)	C3—C12—O14—C15	175.0 (2)
C3—C2—C7—S8	−65.8 (3)	C16—C15—O14—C12	−89.3 (4)
N1—C2—C7—S8	116.07 (19)	O23—C22—O24—C25	−4.2 (4)
S8—C9—C10—N12	−38.0 (3)	C5—C22—O24—C25	173.8 (2)
C2—C7—N12—C10	96.5 (2)	C26—C25—O24—C22	−177.7 (4)
S8—C7—N12—C10	−25.0 (2)	C10—C9—S8—C7	20.1 (2)
C9—C10—N12—C7	41.9 (3)	N12—C7—S8—C9	1.93 (18)
C2—C3—C12—O13	8.8 (4)	C2—C7—S8—C9	−122.50 (19)
C4—C3—C12—O13	−170.6 (2)	C20—C19—S18—C17	−0.1 (3)
C2—C3—C12—O14	−171.5 (2)	C21—C17—S18—C19	−0.1 (2)
C4—C3—C12—O14	9.1 (3)	C4—C17—S18—C19	179.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N12	0.86	2.27	2.652 (2)	107