N-p-Tolyl-pyrrolidine-1-carboxamide.

In the title mol-ecule, C(12)H(16)N(2)O, the pyrrolidine ring has a half-chair conformation. In the crystal, mol-ecules 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 = 204.27

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.183

S = 1.14

2553 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 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/S1600536812013578/lh5444sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812013578/lh5444Isup3.cml

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

C12H16N2O	F(000) = 440
Mr = 204.27	Dx = 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

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

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(Fo2) + (0.0942P)2 + 0.2108P] where P = (Fo2 + 2Fc2)/3
2553 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 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
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*

	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)

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

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

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) .