N-(4-Chloro­phen­yl)pyrrolidine-1-carboxamide

Li, Y.-F.

doi:10.1107/S1600536811024111

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1792

doi:10.1107/S1600536811024111

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N-(4-Chlorophenyl)pyrrolidine-1-carboxamide

Yu-Feng Li ^a ^*

^aMicroscale Science Institute, Department of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
^*Correspondence e-mail: liyufeng8111@163.com

(Received 19 May 2011; accepted 20 June 2011; online 25 June 2011)

In the title molecule, C₁₁H₁₃ClN₂O, the five-membered ring has an envelope conformation. In the crystal, molecules are linked into chains along [100] by intermolecular N—H⋯O hydrogen bonds.

Related literature

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997 ). For a related structure, see: Köhn et al. (2004 ).

Experimental

Crystal data

C₁₁H₁₃ClN₂O
M_r = 224.68
Orthorhombic, P b c a
a = 9.4498 (19) Å
b = 10.856 (2) Å
c = 21.930 (4) Å
V = 2249.7 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.23 × 0.19 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
20387 measured reflections
2576 independent reflections
2264 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.130
S = 1.07
2576 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.21	2.9184 (15)	140
Symmetry code: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024111/lh5257sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024111/lh5257Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024111/lh5257Isup3.cml

checkCIF report

Comment top

Pyrrolidine compounds have been shown to have medicinal properties (Yang et al., 1997). The crystal structure of the title compound is presented herein. The molecular structure of the title compound is shown in Fig. 1. The five-membered ring has an envelope conformation with atom C4 forming the flap. In the crystal, the molecules are linked into chains along [100] by intermoecular N—H···O hydrogen bonds. The structure of a related compound has already been determined (Köhn et al., 2004).

Related literature top

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997). For a related structure, see: Köhn et al. (2004).

Experimental top

A mixture of pyrrolidine (0.1 mol), and (4-chlorophenyl)carbamic chloride (0.1 mol) was stirred in refluxing ethanol (20 ml) for 4 h to afford the title compound (0.079 mol, yield 79%). Colourless blocks of the title compound were obtained by recrystallization of a solution of the title compound ethanol at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.

N-(4-Chlorophenyl)pyrrolidine-1-carboxamide top

Crystal data top

C₁₁H₁₃ClN₂O	F(000) = 944
M_r = 224.68	D_x = 1.327 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2264 reflections
a = 9.4498 (19) Å	θ = 3.0–27.6°
b = 10.856 (2) Å	µ = 0.31 mm⁻¹
c = 21.930 (4) Å	T = 293 K
V = 2249.7 (8) Å³	Bar, colorless
Z = 8	0.23 × 0.19 × 0.19 mm

Data collection top

Bruker SMART CCD diffractometer	2264 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.036
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −12→10
20387 measured reflections	k = −14→14
2576 independent reflections	l = −28→28

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) = 0.130	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0763P)² + 0.5404P] where P = (F_o² + 2F_c²)/3
2576 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₁H₁₃ClN₂O	V = 2249.7 (8) Å³
M_r = 224.68	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.4498 (19) Å	µ = 0.31 mm⁻¹
b = 10.856 (2) Å	T = 293 K
c = 21.930 (4) Å	0.23 × 0.19 × 0.19 mm

Data collection top

Bruker SMART CCD diffractometer	2264 reflections with I > 2σ(I)
20387 measured reflections	R_int = 0.036
2576 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.07	Δρ_max = 0.55 e Å⁻³
2576 reflections	Δρ_min = −0.33 e Å⁻³
136 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
Cl1	0.10254 (6)	0.10302 (5)	0.03994 (2)	0.0685 (2)
O1	0.12968 (10)	0.43109 (12)	0.28838 (5)	0.0496 (3)
N2	0.34453 (11)	0.36694 (12)	0.25166 (5)	0.0388 (3)
H2A	0.4347	0.3673	0.2570	0.047*
C6	0.28726 (13)	0.30130 (12)	0.20175 (6)	0.0347 (3)
C10	0.12280 (16)	0.15354 (14)	0.16052 (7)	0.0434 (3)
H10A	0.0507	0.0963	0.1660	0.052*
C5	0.26031 (14)	0.43003 (13)	0.29184 (6)	0.0356 (3)
C11	0.17977 (15)	0.21521 (13)	0.20997 (6)	0.0393 (3)
H11A	0.1460	0.1990	0.2490	0.047*
N1	0.32890 (12)	0.49261 (12)	0.33577 (5)	0.0417 (3)
C9	0.17459 (17)	0.17824 (14)	0.10291 (7)	0.0445 (3)
C7	0.34090 (16)	0.32181 (14)	0.14377 (7)	0.0420 (3)
H7A	0.4150	0.3770	0.1383	0.050*
C1	0.47839 (15)	0.47967 (16)	0.35253 (7)	0.0463 (4)
H1A	0.5367	0.5390	0.3310	0.056*
H1B	0.5127	0.3973	0.3439	0.056*
C8	0.28451 (17)	0.26042 (15)	0.09408 (7)	0.0460 (4)
H8A	0.3202	0.2743	0.0552	0.055*
C2	0.24919 (18)	0.5611 (2)	0.38171 (8)	0.0584 (5)
H2B	0.1790	0.5091	0.4012	0.070*
H2C	0.2023	0.6319	0.3638	0.070*
C4	0.4771 (2)	0.5051 (2)	0.42042 (8)	0.0633 (5)
H4A	0.4543	0.4313	0.4434	0.076*
H4B	0.5677	0.5367	0.4341	0.076*
C3	0.3624 (2)	0.6009 (2)	0.42688 (10)	0.0748 (7)
H3A	0.3981	0.6822	0.4169	0.090*
H3B	0.3253	0.6021	0.4681	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0781 (4)	0.0754 (4)	0.0520 (3)	−0.0222 (2)	−0.0144 (2)	−0.0182 (2)
O1	0.0252 (5)	0.0734 (8)	0.0503 (6)	−0.0018 (5)	−0.0022 (4)	−0.0141 (5)
N2	0.0250 (5)	0.0529 (7)	0.0385 (6)	−0.0035 (4)	−0.0019 (5)	−0.0104 (5)
C6	0.0300 (6)	0.0374 (7)	0.0366 (6)	−0.0003 (5)	−0.0028 (5)	−0.0035 (5)
C10	0.0401 (7)	0.0376 (7)	0.0525 (8)	−0.0078 (6)	−0.0040 (6)	−0.0022 (6)
C5	0.0273 (6)	0.0462 (7)	0.0333 (6)	−0.0018 (5)	−0.0008 (5)	−0.0012 (5)
C11	0.0378 (7)	0.0399 (7)	0.0403 (7)	−0.0038 (5)	−0.0005 (5)	0.0017 (5)
N1	0.0278 (6)	0.0607 (8)	0.0366 (6)	0.0020 (5)	−0.0021 (5)	−0.0122 (5)
C9	0.0476 (8)	0.0423 (7)	0.0435 (7)	−0.0040 (6)	−0.0103 (6)	−0.0082 (6)
C7	0.0407 (7)	0.0434 (7)	0.0420 (7)	−0.0097 (6)	0.0024 (6)	−0.0037 (6)
C1	0.0304 (7)	0.0660 (9)	0.0427 (7)	0.0017 (6)	−0.0066 (6)	−0.0109 (7)
C8	0.0516 (8)	0.0499 (8)	0.0366 (7)	−0.0080 (6)	0.0007 (6)	−0.0041 (6)
C2	0.0386 (7)	0.0854 (12)	0.0511 (9)	0.0037 (8)	0.0039 (7)	−0.0269 (9)
C4	0.0507 (10)	0.0972 (14)	0.0419 (8)	−0.0043 (9)	−0.0111 (7)	−0.0109 (8)
C3	0.0550 (10)	0.1115 (18)	0.0580 (11)	−0.0022 (11)	−0.0013 (9)	−0.0434 (11)

Geometric parameters (Å, º) top

Cl1—C9	1.7428 (15)	C7—C8	1.384 (2)
O1—C5	1.2368 (17)	C7—H7A	0.9300
N2—C5	1.3707 (18)	C1—C4	1.514 (2)
N2—C6	1.4138 (16)	C1—H1A	0.9700
N2—H2A	0.8600	C1—H1B	0.9700
C6—C7	1.387 (2)	C8—H8A	0.9300
C6—C11	1.3920 (19)	C2—C3	1.521 (3)
C10—C9	1.381 (2)	C2—H2B	0.9700
C10—C11	1.383 (2)	C2—H2C	0.9700
C10—H10A	0.9300	C4—C3	1.509 (3)
C5—N1	1.3453 (17)	C4—H4A	0.9700
C11—H11A	0.9300	C4—H4B	0.9700
N1—C2	1.4612 (19)	C3—H3A	0.9700
N1—C1	1.4664 (18)	C3—H3B	0.9700
C9—C8	1.383 (2)

C5—N2—C6	121.82 (11)	C4—C1—H1A	111.2
C5—N2—H2A	119.1	N1—C1—H1B	111.2
C6—N2—H2A	119.1	C4—C1—H1B	111.2
C7—C6—C11	119.55 (12)	H1A—C1—H1B	109.1
C7—C6—N2	119.27 (12)	C9—C8—C7	119.31 (14)
C11—C6—N2	121.17 (12)	C9—C8—H8A	120.3
C9—C10—C11	119.02 (13)	C7—C8—H8A	120.3
C9—C10—H10A	120.5	N1—C2—C3	103.37 (14)
C11—C10—H10A	120.5	N1—C2—H2B	111.1
O1—C5—N1	121.34 (13)	C3—C2—H2B	111.1
O1—C5—N2	123.01 (12)	N1—C2—H2C	111.1
N1—C5—N2	115.65 (12)	C3—C2—H2C	111.1
C10—C11—C6	120.49 (13)	H2B—C2—H2C	109.1
C10—C11—H11A	119.8	C3—C4—C1	102.93 (15)
C6—C11—H11A	119.8	C3—C4—H4A	111.2
C5—N1—C2	120.15 (12)	C1—C4—H4A	111.2
C5—N1—C1	126.53 (12)	C3—C4—H4B	111.2
C2—N1—C1	111.87 (12)	C1—C4—H4B	111.2
C10—C9—C8	121.30 (13)	H4A—C4—H4B	109.1
C10—C9—Cl1	119.70 (12)	C4—C3—C2	104.35 (15)
C8—C9—Cl1	118.99 (12)	C4—C3—H3A	110.9
C8—C7—C6	120.25 (13)	C2—C3—H3A	110.9
C8—C7—H7A	119.9	C4—C3—H3B	110.9
C6—C7—H7A	119.9	C2—C3—H3B	110.9
N1—C1—C4	102.78 (13)	H3A—C3—H3B	108.9
N1—C1—H1A	111.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.21	2.9184 (15)	140

Symmetry code: (i) x+1/2, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃ClN₂O
M_r	224.68
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	9.4498 (19), 10.856 (2), 21.930 (4)
V (Å³)	2249.7 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.23 × 0.19 × 0.19

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	20387, 2576, 2264
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.130, 1.07
No. of reflections	2576
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.33

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.21	2.9184 (15)	140

Symmetry code: (i) x+1/2, y, −z+1/2.

Acknowledgements

The author would like to thank the Natural Science Foundation of Shandong Province (No. Y2008B23).

References

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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