N-(2,3,4-Trifluoro-phen-yl)pyrrolidine-1-carboxamide.

In the title compound, C(11)H(11)F(3)N(2)O, a urea derivative, the best plane through the pyrrole ring makes a dihedral angle of 9.69 (13)° with the benzene ring. The amino H atom is shielded, so that it is not involved in any hydrogen-bonding inter-actions.

Related literature

For background to this class of compounds, see Zheng et al. (2010 ▶).

Experimental

Crystal data

C11H11F3N2O

M = 244.22

Monoclinic,

a = 6.0708 (4) Å

b = 24.2124 (15) Å

c = 7.4232 (6) Å

β = 100.508 (7)°

V = 1072.83 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.35 × 0.35 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.964, T max = 1.000

4465 measured reflections

2190 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.151

S = 1.04

2190 reflections

158 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051385/bt5716sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051385/bt5716Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051385/bt5716Isup3.cml

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

C11H11F3N2O	F(000) = 504
Mr = 244.22	Dx = 1.512 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 6.0708 (4) Å	Cell parameters from 1445 reflections
b = 24.2124 (15) Å	θ = 2.9–28.9°
c = 7.4232 (6) Å	µ = 0.13 mm−1
β = 100.508 (7)°	T = 293 K
V = 1072.83 (13) Å3	Block, colorless
Z = 4	0.35 × 0.35 × 0.25 mm

Oxford Diffraction Xcalibur Eos diffractometer	2190 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1374 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.0874 pixels mm-1	θmax = 26.4°, θmin = 2.9°
ω scans	h = −7→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −30→27
Tmin = 0.964, Tmax = 1.000	l = −8→9
4465 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.055P)2 + 0.3084P] where P = (Fo2 + 2Fc2)/3
2190 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.22 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
F1	0.1373 (2)	−0.04074 (6)	0.1339 (2)	0.0855 (6)
F2	0.2120 (3)	−0.14684 (7)	0.2355 (3)	0.0987 (7)
F3	0.6185 (3)	−0.17950 (6)	0.4120 (2)	0.0908 (6)
O1	0.7849 (3)	0.08144 (8)	0.2954 (3)	0.0827 (6)
N1	0.4504 (4)	0.03783 (9)	0.2033 (3)	0.0586 (6)
H1	0.325 (4)	0.0407 (10)	0.159 (4)	0.061 (9)*
N2	0.4818 (3)	0.13161 (8)	0.1745 (3)	0.0577 (6)
C1	0.3428 (4)	−0.05587 (11)	0.2237 (3)	0.0577 (6)
C2	0.3786 (5)	−0.10989 (11)	0.2741 (4)	0.0626 (7)
C3	0.5855 (5)	−0.12546 (11)	0.3645 (4)	0.0649 (7)
C4	0.7542 (5)	−0.08815 (11)	0.4034 (4)	0.0676 (7)
H4	0.8950	−0.0992	0.4640	0.081*
C5	0.7159 (4)	−0.03335 (11)	0.3522 (4)	0.0645 (7)
H5	0.8315	−0.0078	0.3799	0.077*
C6	0.5075 (4)	−0.01615 (10)	0.2603 (3)	0.0521 (6)
C7	0.5845 (4)	0.08395 (10)	0.2289 (3)	0.0558 (6)
C8	0.2441 (4)	0.13970 (10)	0.1006 (4)	0.0637 (7)
H8A	0.1513	0.1238	0.1807	0.076*
H8B	0.2032	0.1234	−0.0203	0.076*
C9	0.2219 (5)	0.20173 (12)	0.0924 (5)	0.0955 (11)
H9A	0.1181	0.2128	−0.0170	0.115*
H9B	0.1664	0.2153	0.1987	0.115*
C10	0.4431 (5)	0.22379 (13)	0.0893 (5)	0.0987 (11)
H10A	0.4614	0.2594	0.1501	0.118*
H10B	0.4652	0.2284	−0.0359	0.118*
C11	0.6072 (5)	0.18321 (11)	0.1877 (4)	0.0744 (8)
H11A	0.7371	0.1800	0.1293	0.089*
H11B	0.6562	0.1939	0.3146	0.089*

	U11	U22	U33	U12	U13	U23
F1	0.0581 (10)	0.0683 (10)	0.1208 (14)	−0.0094 (8)	−0.0083 (9)	0.0058 (9)
F2	0.0865 (13)	0.0638 (10)	0.1378 (17)	−0.0188 (9)	−0.0004 (11)	0.0062 (10)
F3	0.1087 (15)	0.0639 (11)	0.0979 (14)	0.0123 (9)	0.0135 (10)	0.0105 (9)
O1	0.0462 (11)	0.0746 (13)	0.1207 (18)	−0.0060 (9)	−0.0020 (10)	0.0012 (11)
N1	0.0477 (13)	0.0583 (14)	0.0662 (15)	−0.0060 (11)	0.0010 (11)	−0.0014 (10)
N2	0.0468 (12)	0.0521 (12)	0.0723 (14)	−0.0087 (10)	0.0060 (10)	−0.0041 (10)
C1	0.0524 (15)	0.0623 (16)	0.0570 (15)	−0.0028 (13)	0.0064 (11)	−0.0034 (12)
C2	0.0659 (17)	0.0541 (16)	0.0686 (17)	−0.0082 (14)	0.0147 (13)	−0.0042 (13)
C3	0.082 (2)	0.0562 (16)	0.0581 (16)	0.0061 (15)	0.0158 (14)	−0.0003 (12)
C4	0.0633 (17)	0.0739 (18)	0.0628 (17)	0.0100 (15)	0.0039 (13)	0.0012 (14)
C5	0.0563 (16)	0.0664 (17)	0.0675 (17)	−0.0033 (14)	0.0029 (12)	−0.0041 (13)
C6	0.0538 (15)	0.0576 (15)	0.0451 (14)	−0.0014 (12)	0.0097 (11)	−0.0049 (11)
C7	0.0506 (15)	0.0584 (15)	0.0588 (15)	−0.0065 (13)	0.0112 (11)	−0.0061 (12)
C8	0.0516 (15)	0.0632 (16)	0.0736 (18)	−0.0067 (13)	0.0045 (12)	0.0055 (13)
C9	0.069 (2)	0.069 (2)	0.144 (3)	−0.0005 (17)	0.007 (2)	0.0207 (19)
C10	0.082 (2)	0.0619 (19)	0.146 (3)	−0.0105 (18)	0.003 (2)	0.0102 (19)
C11	0.0585 (17)	0.0621 (17)	0.101 (2)	−0.0144 (14)	0.0086 (15)	−0.0058 (15)

F1—C1	1.353 (3)	C4—C5	1.388 (4)
F2—C2	1.341 (3)	C5—H5	0.9300
F3—C3	1.360 (3)	C5—C6	1.387 (3)
O1—C7	1.228 (3)	C8—H8A	0.9700
N1—H1	0.77 (3)	C8—H8B	0.9700
N1—C6	1.398 (3)	C8—C9	1.508 (4)
N1—C7	1.375 (3)	C9—H9A	0.9700
N2—C7	1.338 (3)	C9—H9B	0.9700
N2—C8	1.461 (3)	C9—C10	1.449 (4)
N2—C11	1.457 (3)	C10—H10A	0.9700
C1—C2	1.367 (4)	C10—H10B	0.9700
C1—C6	1.378 (3)	C10—C11	1.492 (4)
C2—C3	1.365 (4)	C11—H11A	0.9700
C3—C4	1.357 (4)	C11—H11B	0.9700
C4—H4	0.9300
C6—N1—H1	112.6 (19)	N2—C7—N1	115.3 (2)
C7—N1—H1	120 (2)	N2—C8—H8A	111.2
C7—N1—C6	127.6 (2)	N2—C8—H8B	111.2
C7—N2—C8	127.1 (2)	N2—C8—C9	102.9 (2)
C7—N2—C11	120.7 (2)	H8A—C8—H8B	109.1
C11—N2—C8	112.3 (2)	C9—C8—H8A	111.2
F1—C1—C2	118.7 (2)	C9—C8—H8B	111.2
F1—C1—C6	118.6 (2)	C8—C9—H9A	110.3
C2—C1—C6	122.7 (2)	C8—C9—H9B	110.3
F2—C2—C1	120.2 (2)	H9A—C9—H9B	108.6
F2—C2—C3	120.7 (2)	C10—C9—C8	106.9 (2)
C3—C2—C1	119.0 (2)	C10—C9—H9A	110.3
F3—C3—C2	118.2 (3)	C10—C9—H9B	110.3
C4—C3—F3	121.0 (3)	C9—C10—H10A	110.4
C4—C3—C2	120.8 (3)	C9—C10—H10B	110.4
C3—C4—H4	120.1	C9—C10—C11	106.7 (3)
C3—C4—C5	119.7 (3)	H10A—C10—H10B	108.6
C5—C4—H4	120.1	C11—C10—H10A	110.4
C4—C5—H5	119.5	C11—C10—H10B	110.4
C6—C5—C4	120.9 (3)	N2—C11—C10	103.7 (2)
C6—C5—H5	119.5	N2—C11—H11A	111.0
C1—C6—N1	117.5 (2)	N2—C11—H11B	111.0
C1—C6—C5	116.8 (2)	C10—C11—H11A	111.0
C5—C6—N1	125.7 (2)	C10—C11—H11B	111.0
O1—C7—N1	122.3 (2)	H11A—C11—H11B	109.0
O1—C7—N2	122.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···F1	0.77 (3)	2.27 (3)	2.672 (3)	113 (2)