N-p-Tolyl­pyrrolidine-1-carboxamide

Li, Y.-F.

doi:10.1107/S1600536812013578

organic compounds

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Volume 68| Part 5| May 2012| Page o1275

doi:10.1107/S1600536812013578

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N-p-Tolylpyrrolidine-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 23 March 2012; accepted 29 March 2012; online 4 April 2012)

In the title molecule, C₁₂H₁₆N₂O, the pyrrolidine ring has a half-chair conformation. In the crystal, molecules are linked into C(4) chains along [001] by N—H⋯O hydrogen bonds.

Related literature

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997 ). For related structures, see: Köhn et al. (2004 ); Li (2011 ).

Experimental

Crystal data

C₁₂H₁₆N₂O
M_r = 204.27
Monoclinic, P 2₁ /c
a = 10.264 (2) Å
b = 10.803 (2) Å
c = 10.168 (2) Å
β = 98.61 (3)°
V = 1114.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker SMART CCD diffractometer
10539 measured reflections
2553 independent reflections
1897 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.183
S = 1.14
2553 reflections
136 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.23 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	2.11	2.9301 (17)	160
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812013578/lh5444sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812013578/lh5444Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812013578/lh5444Isup3.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 pyrrolidine ring has a half-chair conformation with atoms C10 and C11 forming the twist. In the crystal, the molecules are linked into chains along [001] by intermoecular N—H···O hydrogen bonds. The structures of related compounds have already been determined (Köhn et al., 2004; Li, 2011).

Related literature top

For the medicinal properties of pyrrolidine compounds, see: Yang et al. (1997). For related structures, see: Köhn et al. (2004); Li (2011).

Experimental top

A mixture of pyrrolidine (0.1 mol), and p-tolylcarbamic chloride (0.1 mol) was stirred in refluxing ethanol (20 ml) for 4 h to afford the title compound (0.068 mol, yield 68%). Colourless blocks of the title compound were obtained by recrystallization of a solution of the title compound in 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-p-Tolylpyrrolidine-1-carboxamide top

Crystal data top

C₁₂H₁₆N₂O	F(000) = 440
M_r = 204.27	D_x = 1.217 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1897 reflections
a = 10.264 (2) Å	θ = 3.2–27.5°
b = 10.803 (2) Å	µ = 0.08 mm⁻¹
c = 10.168 (2) Å	T = 293 K
β = 98.61 (3)°	Block, colorless
V = 1114.7 (4) Å³	0.25 × 0.22 × 0.19 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 27.5°, θ_min = 3.2°
ϕ and ω scans	h = −13→13
10539 measured reflections	k = −14→13
2553 independent reflections	l = −11→13

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0942P)² + 0.2108P] where P = (F_o² + 2F_c²)/3
2553 reflections	(Δ/σ)_max < 0.001
136 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₂H₁₆N₂O	V = 1114.7 (4) Å³
M_r = 204.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.264 (2) Å	µ = 0.08 mm⁻¹
b = 10.803 (2) Å	T = 293 K
c = 10.168 (2) Å	0.25 × 0.22 × 0.19 mm
β = 98.61 (3)°

Data collection top

Bruker SMART CCD diffractometer	1897 reflections with I > 2σ(I)
10539 measured reflections	R_int = 0.028
2553 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.14	Δρ_max = 0.28 e Å⁻³
2553 reflections	Δρ_min = −0.23 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
N2	0.56448 (13)	0.21960 (13)	−0.00416 (12)	0.0472 (4)
H2A	0.5404	0.2325	−0.0877	0.057*
O1	0.53582 (13)	0.27916 (14)	0.20476 (11)	0.0635 (4)
C8	0.50216 (15)	0.28509 (16)	0.08300 (14)	0.0448 (4)
N1	0.40218 (14)	0.35882 (14)	0.02833 (13)	0.0503 (4)
C5	0.66558 (15)	0.13221 (15)	0.03298 (14)	0.0429 (4)
C4	0.66667 (17)	0.02489 (17)	−0.04178 (16)	0.0509 (4)
H4A	0.6007	0.0116	−0.1137	0.061*
C6	0.76598 (17)	0.15035 (17)	0.13941 (17)	0.0530 (4)
H6A	0.7679	0.2219	0.1905	0.064*
C7	0.86316 (17)	0.06128 (18)	0.16900 (18)	0.0562 (5)
H7A	0.9295	0.0746	0.2405	0.067*
C2	0.86506 (17)	−0.04686 (16)	0.09602 (19)	0.0533 (4)
C3	0.76466 (18)	−0.06224 (17)	−0.01046 (19)	0.0562 (5)
H3A	0.7634	−0.1333	−0.0622	0.067*
C9	0.34923 (18)	0.36700 (19)	−0.11286 (16)	0.0563 (5)
H9A	0.3101	0.2890	−0.1455	0.068*
H9B	0.4176	0.3892	−0.1648	0.068*
C1	0.9702 (2)	−0.1433 (2)	0.1322 (3)	0.0733 (6)
H1A	1.0299	−0.1161	0.2086	0.110*
H1B	1.0177	−0.1554	0.0588	0.110*
H1C	0.9300	−0.2198	0.1525	0.110*
C12	0.3266 (2)	0.4321 (2)	0.1112 (2)	0.0659 (5)
H12A	0.3783	0.5009	0.1520	0.079*
H12B	0.2981	0.3816	0.1805	0.079*
C10	0.2464 (2)	0.4672 (2)	−0.1194 (2)	0.0706 (6)
H10A	0.2814	0.5451	−0.1461	0.085*
H10B	0.1697	0.4455	−0.1830	0.085*
C11	0.2112 (3)	0.4770 (3)	0.0157 (2)	0.0874 (8)
H11A	0.1342	0.4269	0.0229	0.105*
H11B	0.1915	0.5623	0.0351	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0509 (8)	0.0620 (9)	0.0274 (6)	0.0059 (6)	0.0014 (5)	0.0021 (6)
O1	0.0667 (8)	0.0948 (11)	0.0277 (6)	0.0111 (7)	0.0033 (5)	−0.0012 (6)
C8	0.0460 (8)	0.0563 (9)	0.0314 (7)	−0.0047 (7)	0.0039 (6)	0.0000 (6)
N1	0.0524 (8)	0.0602 (8)	0.0374 (7)	0.0059 (6)	0.0038 (6)	−0.0029 (6)
C5	0.0433 (8)	0.0521 (9)	0.0326 (7)	−0.0033 (6)	0.0040 (6)	0.0049 (6)
C4	0.0504 (9)	0.0588 (10)	0.0412 (8)	−0.0037 (7)	−0.0007 (7)	−0.0032 (7)
C6	0.0500 (9)	0.0587 (10)	0.0465 (9)	−0.0045 (7)	−0.0045 (7)	−0.0035 (8)
C7	0.0458 (9)	0.0646 (11)	0.0536 (10)	−0.0048 (8)	−0.0073 (7)	0.0047 (8)
C2	0.0461 (9)	0.0530 (9)	0.0609 (10)	−0.0048 (7)	0.0080 (7)	0.0134 (8)
C3	0.0567 (10)	0.0528 (10)	0.0585 (10)	−0.0036 (8)	0.0069 (8)	−0.0011 (8)
C9	0.0544 (10)	0.0718 (12)	0.0407 (8)	0.0055 (8)	0.0005 (7)	0.0075 (8)
C1	0.0562 (11)	0.0650 (12)	0.0964 (16)	0.0038 (9)	0.0036 (11)	0.0148 (11)
C12	0.0646 (12)	0.0769 (13)	0.0567 (11)	0.0122 (10)	0.0108 (9)	−0.0096 (9)
C10	0.0653 (12)	0.0741 (13)	0.0680 (13)	0.0141 (10)	−0.0041 (10)	0.0060 (10)
C11	0.0789 (15)	0.1071 (19)	0.0773 (15)	0.0339 (14)	0.0155 (12)	0.0033 (14)

Geometric parameters (Å, º) top

N2—C8	1.366 (2)	C2—C1	1.505 (3)
N2—C5	1.412 (2)	C3—H3A	0.9300
N2—H2A	0.8600	C9—C10	1.506 (3)
O1—C8	1.2362 (18)	C9—H9A	0.9700
C8—N1	1.351 (2)	C9—H9B	0.9700
N1—C9	1.460 (2)	C1—H1A	0.9600
N1—C12	1.461 (2)	C1—H1B	0.9600
C5—C4	1.387 (2)	C1—H1C	0.9600
C5—C6	1.392 (2)	C12—C11	1.496 (3)
C4—C3	1.379 (3)	C12—H12A	0.9700
C4—H4A	0.9300	C12—H12B	0.9700
C6—C7	1.386 (2)	C10—C11	1.477 (3)
C6—H6A	0.9300	C10—H10A	0.9700
C7—C2	1.386 (3)	C10—H10B	0.9700
C7—H7A	0.9300	C11—H11A	0.9700
C2—C3	1.388 (3)	C11—H11B	0.9700

C8—N2—C5	124.74 (13)	C10—C9—H9A	110.9
C8—N2—H2A	117.6	N1—C9—H9B	110.9
C5—N2—H2A	117.6	C10—C9—H9B	110.9
O1—C8—N1	121.58 (15)	H9A—C9—H9B	109.0
O1—C8—N2	122.36 (15)	C2—C1—H1A	109.5
N1—C8—N2	116.05 (13)	C2—C1—H1B	109.5
C8—N1—C9	126.04 (14)	H1A—C1—H1B	109.5
C8—N1—C12	121.21 (14)	C2—C1—H1C	109.5
C9—N1—C12	112.52 (14)	H1A—C1—H1C	109.5
C4—C5—C6	118.55 (15)	H1B—C1—H1C	109.5
C4—C5—N2	118.57 (14)	N1—C12—C11	103.79 (16)
C6—C5—N2	122.87 (15)	N1—C12—H12A	111.0
C3—C4—C5	120.61 (15)	C11—C12—H12A	111.0
C3—C4—H4A	119.7	N1—C12—H12B	111.0
C5—C4—H4A	119.7	C11—C12—H12B	111.0
C7—C6—C5	119.73 (16)	H12A—C12—H12B	109.0
C7—C6—H6A	120.1	C11—C10—C9	106.14 (17)
C5—C6—H6A	120.1	C11—C10—H10A	110.5
C2—C7—C6	122.44 (16)	C9—C10—H10A	110.5
C2—C7—H7A	118.8	C11—C10—H10B	110.5
C6—C7—H7A	118.8	C9—C10—H10B	110.5
C7—C2—C3	116.75 (16)	H10A—C10—H10B	108.7
C7—C2—C1	121.30 (17)	C10—C11—C12	107.49 (19)
C3—C2—C1	121.95 (18)	C10—C11—H11A	110.2
C4—C3—C2	121.92 (17)	C12—C11—H11A	110.2
C4—C3—H3A	119.0	C10—C11—H11B	110.2
C2—C3—H3A	119.0	C12—C11—H11B	110.2
N1—C9—C10	104.03 (16)	H11A—C11—H11B	108.5
N1—C9—H9A	110.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.11	2.9301 (17)	160

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₂O
M_r	204.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.264 (2), 10.803 (2), 10.168 (2)
β (°)	98.61 (3)
V (Å³)	1114.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.22 × 0.19

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	10539, 2553, 1897
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.183, 1.14
No. of reflections	2553
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.23

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	2.11	2.9301 (17)	160.0

Symmetry code: (i) x, −y+1/2, z−1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Köhn, U., Günther, W., Görls, H. & Anders, E. (2004). Tetrahedron Asymmetry, 15, 1419–1426. Google Scholar
Li, Y.-F. (2011). Acta Cryst. E67, o1792. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D., Soulier, J. L., Sicsic, S., Mathe-Allainmat, M., Bremont, B., Croci, T., Cardamone, R., Aureggi, G. & Langlois, M. (1997). J. Med. Chem. 40, 608–621. CSD CrossRef CAS PubMed Web of Science Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1275

doi:10.1107/S1600536812013578

Open

access