N-(4-Chloro-phen-yl)pyrrolidine-1-carboxamide.

In the title mol-ecule, C(11)H(13)ClN(2)O, the five-membered ring has an envelope conformation. In the crystal, mol-ecules are linked into chains along [100] by inter-molecular 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 = 224.68

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.07

2576 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811024111/lh5257sup1.cif

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

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

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

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

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 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

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
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*

	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)

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

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

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) .