Ethyl 2-(3-chloro-2-pyridyl)-5-oxopyrazolidine-3-carboxylate.

In the mol-ecule of the title compound, C(11)H(12)ClN(3)O(3), the five membered ring adopts an envelope conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric dimers.

Related literature

For the synthetic procedure, see: Lahm et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H12ClN3O3

M = 269.69

Orthorhombic,

a = 15.488 (3) Å

b = 10.009 (2) Å

c = 16.249 (3) Å

V = 2518.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.31 mm−1

T = 298 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.913, T max = 0.970

4453 measured reflections

2273 independent reflections

1635 reflections with I > 2σ(I)

R int = 0.029

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.110

S = 1.03

2273 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809020789/hk2697sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020789/hk2697Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C11H12ClN3O3	F(000) = 1120
Mr = 269.69	Dx = 1.422 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 15.488 (3) Å	θ = 0.9–1.0°
b = 10.009 (2) Å	µ = 0.31 mm−1
c = 16.249 (3) Å	T = 298 K
V = 2518.9 (8) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1635 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
graphite	θmax = 25.3°, θmin = 2.5°
ω/2θ scans	h = 0→18
Absorption correction: ψ scan (North et al., 1968)	k = 0→12
Tmin = 0.913, Tmax = 0.970	l = −19→19
4453 measured reflections	3 standard reflections every 120 min
2273 independent reflections	intensity decay: none

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.110	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.824P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2273 reflections	Δρmax = 0.29 e Å−3
164 parameters	Δρmin = −0.23 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (7)

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.

	x	y	z	Uiso*/Ueq
Cl	0.45523 (4)	0.14184 (7)	0.43566 (5)	0.0629 (3)
O1	0.30427 (10)	0.43898 (19)	0.31272 (11)	0.0561 (5)
O2	0.34478 (11)	0.4578 (2)	0.44373 (11)	0.0597 (5)
O3	0.55616 (12)	0.7407 (2)	0.33051 (13)	0.0667 (6)
N1	0.54947 (12)	0.55100 (18)	0.40815 (12)	0.0372 (5)
H1A	0.5776	0.5814	0.4497	0.045*
N2	0.51613 (11)	0.41865 (17)	0.40548 (11)	0.0328 (4)
N3	0.66149 (12)	0.3566 (2)	0.37919 (13)	0.0456 (5)
C1	0.1756 (2)	0.3232 (4)	0.3592 (2)	0.0876 (11)
H1B	0.1163	0.3358	0.3745	0.131*
H1C	0.2069	0.2863	0.4049	0.131*
H1D	0.1789	0.2631	0.3133	0.131*
C2	0.21401 (15)	0.4539 (3)	0.3359 (2)	0.0666 (9)
H2A	0.1820	0.4915	0.2902	0.080*
H2B	0.2096	0.5152	0.3820	0.080*
C3	0.36204 (14)	0.4419 (2)	0.37295 (15)	0.0389 (6)
C4	0.45184 (14)	0.4216 (2)	0.33772 (13)	0.0363 (5)
H4A	0.4542	0.3381	0.3063	0.044*
C5	0.48079 (15)	0.5388 (3)	0.28374 (15)	0.0471 (6)
H5A	0.5154	0.5078	0.2378	0.056*
H5B	0.4315	0.5878	0.2627	0.056*
C6	0.53378 (15)	0.6246 (3)	0.34130 (15)	0.0434 (6)
C7	0.58184 (14)	0.3194 (2)	0.39697 (13)	0.0332 (5)
C8	0.72260 (16)	0.2612 (3)	0.37550 (18)	0.0565 (8)
H8A	0.7790	0.2872	0.3639	0.068*
C9	0.70658 (18)	0.1279 (3)	0.38781 (17)	0.0548 (7)
H9A	0.7509	0.0655	0.3842	0.066*
C10	0.62367 (17)	0.0884 (3)	0.40552 (16)	0.0490 (6)
H10A	0.6104	−0.0013	0.4134	0.059*
C11	0.56048 (14)	0.1858 (2)	0.41127 (15)	0.0389 (6)

	U11	U22	U33	U12	U13	U23
Cl	0.0487 (4)	0.0514 (4)	0.0885 (6)	−0.0128 (3)	0.0079 (4)	0.0135 (4)
O1	0.0322 (9)	0.0815 (14)	0.0546 (11)	0.0039 (9)	−0.0095 (8)	−0.0041 (10)
O2	0.0367 (10)	0.0944 (16)	0.0479 (11)	0.0071 (10)	0.0002 (8)	−0.0127 (11)
O3	0.0629 (12)	0.0508 (12)	0.0864 (16)	−0.0110 (10)	−0.0068 (10)	0.0283 (11)
N1	0.0399 (10)	0.0307 (10)	0.0411 (11)	−0.0008 (8)	−0.0056 (9)	−0.0020 (9)
N2	0.0301 (9)	0.0308 (10)	0.0374 (10)	0.0009 (8)	−0.0036 (8)	−0.0011 (8)
N3	0.0314 (10)	0.0402 (12)	0.0650 (14)	0.0003 (9)	0.0035 (10)	−0.0027 (10)
C1	0.0537 (19)	0.097 (3)	0.112 (3)	−0.0200 (19)	0.0081 (19)	−0.017 (2)
C2	0.0295 (13)	0.087 (2)	0.084 (2)	0.0059 (14)	−0.0081 (14)	−0.0055 (18)
C3	0.0339 (12)	0.0399 (14)	0.0429 (14)	0.0027 (10)	−0.0047 (11)	−0.0039 (11)
C4	0.0342 (11)	0.0409 (13)	0.0339 (12)	0.0046 (10)	−0.0039 (9)	−0.0051 (10)
C5	0.0389 (13)	0.0647 (17)	0.0377 (13)	0.0061 (12)	−0.0017 (10)	0.0091 (12)
C6	0.0364 (13)	0.0465 (16)	0.0474 (15)	0.0045 (11)	0.0034 (11)	0.0107 (12)
C7	0.0318 (11)	0.0340 (12)	0.0337 (12)	0.0022 (10)	−0.0027 (10)	−0.0002 (10)
C8	0.0323 (12)	0.0542 (18)	0.083 (2)	0.0046 (12)	0.0019 (13)	−0.0045 (15)
C9	0.0498 (16)	0.0481 (16)	0.0666 (19)	0.0201 (13)	−0.0077 (14)	−0.0037 (13)
C10	0.0581 (16)	0.0342 (13)	0.0548 (15)	0.0072 (13)	−0.0068 (13)	0.0069 (12)
C11	0.0379 (13)	0.0351 (13)	0.0439 (14)	−0.0019 (10)	−0.0037 (10)	0.0032 (11)

Cl—C11	1.735 (2)	C2—H2A	0.9700
O1—C2	1.456 (3)	C2—H2B	0.9700
O1—C3	1.326 (3)	C3—C4	1.518 (3)
O2—C3	1.191 (3)	C4—C5	1.531 (3)
O3—C6	1.226 (3)	C4—H4A	0.9800
N1—N2	1.422 (2)	C5—C6	1.512 (4)
N1—C6	1.335 (3)	C5—H5A	0.9700
N1—H1A	0.8600	C5—H5B	0.9700
N2—C4	1.485 (3)	C7—C11	1.396 (3)
N2—C7	1.429 (3)	C8—C9	1.372 (4)
N3—C7	1.321 (3)	C8—H8A	0.9300
N3—C8	1.346 (3)	C9—C10	1.374 (4)
C1—C2	1.485 (4)	C9—H9A	0.9300
C1—H1B	0.9600	C10—C11	1.385 (3)
C1—H1C	0.9600	C10—H10A	0.9300
C1—H1D	0.9600
C3—O1—C2	117.0 (2)	C3—C4—H4A	110.1
N2—N1—H1A	122.5	C5—C4—H4A	110.1
C6—N1—N2	115.02 (19)	C6—C5—C4	103.85 (18)
C6—N1—H1A	122.5	C6—C5—H5A	111.0
N1—N2—C7	113.08 (17)	C4—C5—H5A	111.0
N1—N2—C4	104.33 (16)	C6—C5—H5B	111.0
C7—N2—C4	114.82 (17)	C4—C5—H5B	111.0
C7—N3—C8	117.8 (2)	H5A—C5—H5B	109.0
C2—C1—H1B	109.5	O3—C6—N1	126.0 (2)
C2—C1—H1C	109.5	O3—C6—C5	127.1 (2)
H1B—C1—H1C	109.5	N1—C6—C5	106.8 (2)
C2—C1—H1D	109.5	N3—C7—C11	121.9 (2)
H1B—C1—H1D	109.5	N3—C7—N2	119.3 (2)
H1C—C1—H1D	109.5	C11—C7—N2	118.7 (2)
O1—C2—C1	111.1 (2)	N3—C8—C9	123.8 (2)
O1—C2—H2A	109.4	N3—C8—H8A	118.1
C1—C2—H2A	109.4	C9—C8—H8A	118.1
O1—C2—H2B	109.4	C8—C9—C10	118.6 (2)
C1—C2—H2B	109.4	C8—C9—H9A	120.7
H2A—C2—H2B	108.0	C10—C9—H9A	120.7
O2—C3—O1	124.3 (2)	C9—C10—C11	118.2 (2)
O2—C3—C4	126.0 (2)	C9—C10—H10A	120.9
O1—C3—C4	109.70 (19)	C11—C10—H10A	120.9
N2—C4—C3	109.73 (17)	C10—C11—C7	119.7 (2)
N2—C4—C5	104.11 (18)	C10—C11—Cl	120.06 (19)
C3—C4—C5	112.46 (19)	C7—C11—Cl	120.25 (17)
N2—C4—H4A	110.1
C6—N1—N2—C7	108.8 (2)	C4—C5—C6—O3	−164.6 (2)
C6—N1—N2—C4	−16.6 (2)	C4—C5—C6—N1	13.3 (2)
C3—O1—C2—C1	−85.7 (3)	C8—N3—C7—C11	−0.3 (3)
C2—O1—C3—O2	−1.2 (4)	C8—N3—C7—N2	176.9 (2)
C2—O1—C3—C4	178.6 (2)	N1—N2—C7—N3	−10.9 (3)
N1—N2—C4—C3	−97.1 (2)	C4—N2—C7—N3	108.6 (2)
C7—N2—C4—C3	138.54 (19)	N1—N2—C7—C11	166.3 (2)
N1—N2—C4—C5	23.4 (2)	C4—N2—C7—C11	−74.1 (3)
C7—N2—C4—C5	−100.9 (2)	C7—N3—C8—C9	1.1 (4)
O2—C3—C4—N2	2.4 (3)	N3—C8—C9—C10	−0.5 (4)
O1—C3—C4—N2	−177.44 (18)	C8—C9—C10—C11	−0.9 (4)
O2—C3—C4—C5	−113.0 (3)	C9—C10—C11—C7	1.7 (4)
O1—C3—C4—C5	67.2 (2)	C9—C10—C11—Cl	−178.6 (2)
N2—C4—C5—C6	−22.5 (2)	N3—C7—C11—C10	−1.1 (4)
C3—C4—C5—C6	96.2 (2)	N2—C7—C11—C10	−178.3 (2)
N2—N1—C6—O3	179.8 (2)	N3—C7—C11—Cl	179.22 (18)
N2—N1—C6—C5	1.8 (3)	N2—C7—C11—Cl	2.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2i	0.86	2.14	2.910 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2i	0.86	2.14	2.910 (3)	149

Symmetry code: (i) .