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

Abstract

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,

• a = 9.4498 (19) Å

• b = 10.856 (2) Å

• c = 21.930 (4) Å

• V = 2249.7 (8) ų

• 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[F ² > 2σ(F ²)] = 0.046

• wR(F ²) = 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

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.

Supplementary Material

Supplementary material file. DOI: 10.1107/S1600536811024111/lh5257Isup3.cml

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

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) .

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H distances = 0.93–0.97 Å; N—H = 0.86Å and with U_iso(H) = 1.2U_eq(C,N).

Figures

Fig. 1.

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

Crystal data

C11H13ClN2O	F(000) = 944
Mr = 224.68	Dx = 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

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

Refinement

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(Fo2) + (0.0763P)2 + 0.5404P] where P = (Fo2 + 2Fc2)/3
2576 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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

Symmetry codes: (i) x+1/2, y, −z+1/2.