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

In title mol-ecule, C(11)H(11)F(3)N(2)O(2), the central -N-C(=O)-N- unit is essentially planar [maximum deviation = 0.013 (2) Å] and forms a dihedral angle of 57.33 (9)° with the benzene ring. The morpholine ring is in a chair conformation. In the crystal, mol-ecules are linked into chains along [001] by N-H⋯O hydrogen bonds.

Related literature

For background to urea derivatives as anti­bacterial and anti­fungal agents, see: Zheng et al. (2010 ▶).

Experimental

Crystal data

C11H11F3N2O2

M = 260.22

Monoclinic,

a = 7.8515 (4) Å

b = 17.8264 (6) Å

c = 8.6872 (4) Å

β = 109.790 (5)°

V = 1144.09 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Agilent Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.994, T max = 1.000

4250 measured reflections

2009 independent reflections

1587 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.103

S = 1.07

2009 reflections

167 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011) ▶; 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051300/lh5385sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051300/lh5385Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051300/lh5385Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811051300/lh5385Isup4.cml

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

C11H11F3N2O2	F(000) = 536
Mr = 260.22	Dx = 1.511 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.7107 Å
a = 7.8515 (4) Å	Cell parameters from 1772 reflections
b = 17.8264 (6) Å	θ = 3.0–29.1°
c = 8.6872 (4) Å	µ = 0.14 mm−1
β = 109.790 (5)°	T = 293 K
V = 1144.09 (8) Å3	Block, colorless
Z = 4	0.40 × 0.35 × 0.30 mm

Agilent Xcalibur Eos diffractometer	2009 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1587 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 16.0874 pixels mm-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −7→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −13→21
Tmin = 0.994, Tmax = 1.000	l = −10→7
4250 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.044P)2 + 0.1807P] where P = (Fo2 + 2Fc2)/3
2009 reflections	(Δ/σ)max < 0.001
167 parameters	Δρmax = 0.15 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
F1	0.88764 (17)	0.67437 (6)	0.52547 (15)	0.0574 (4)
F2	1.12312 (17)	0.76456 (7)	0.45200 (16)	0.0681 (4)
F3	1.11974 (18)	0.91342 (7)	0.50200 (18)	0.0764 (4)
O1	0.2304 (2)	0.51651 (8)	0.66738 (18)	0.0617 (4)
O2	0.50780 (18)	0.68346 (7)	0.37155 (14)	0.0427 (4)
N1	0.6148 (2)	0.73140 (8)	0.63043 (18)	0.0384 (4)
N2	0.4106 (2)	0.63276 (8)	0.56564 (16)	0.0370 (4)
C1	0.8741 (3)	0.74877 (10)	0.5421 (2)	0.0380 (4)
C2	0.9976 (3)	0.79446 (11)	0.5078 (2)	0.0434 (5)
C3	0.9947 (3)	0.87006 (11)	0.5337 (2)	0.0469 (5)
C4	0.8722 (3)	0.90070 (11)	0.5949 (2)	0.0471 (5)
H4	0.8739	0.9519	0.6159	0.057*
C5	0.7451 (3)	0.85485 (10)	0.6255 (2)	0.0397 (5)
H5	0.6604	0.8757	0.6662	0.048*
C6	0.7420 (2)	0.77841 (9)	0.59651 (19)	0.0331 (4)
C7	0.5081 (2)	0.68272 (9)	0.5135 (2)	0.0328 (4)
C8	0.2658 (3)	0.59059 (10)	0.4469 (2)	0.0422 (5)
H8A	0.2909	0.5865	0.3452	0.051*
H8B	0.1523	0.6173	0.4244	0.051*
C9	0.2489 (3)	0.51341 (11)	0.5100 (3)	0.0546 (6)
H9A	0.1442	0.4885	0.4342	0.065*
H9B	0.3553	0.4842	0.5165	0.065*
C10	0.3837 (3)	0.55182 (12)	0.7792 (2)	0.0587 (6)
H10A	0.4916	0.5240	0.7841	0.070*
H10B	0.3735	0.5512	0.8874	0.070*
C11	0.4023 (3)	0.63175 (11)	0.7304 (2)	0.0484 (5)
H11A	0.2996	0.6610	0.7340	0.058*
H11B	0.5115	0.6538	0.8063	0.058*
H1	0.576 (3)	0.7459 (10)	0.705 (2)	0.039 (5)*

	U11	U22	U33	U12	U13	U23
F1	0.0633 (8)	0.0337 (6)	0.0872 (9)	0.0021 (5)	0.0412 (7)	−0.0068 (6)
F2	0.0613 (8)	0.0643 (8)	0.1001 (10)	0.0016 (6)	0.0552 (8)	−0.0071 (7)
F3	0.0789 (10)	0.0583 (8)	0.1138 (11)	−0.0191 (7)	0.0613 (9)	0.0059 (7)
O1	0.0655 (10)	0.0587 (10)	0.0722 (10)	−0.0197 (8)	0.0380 (9)	0.0057 (8)
O2	0.0571 (9)	0.0439 (8)	0.0345 (7)	−0.0081 (6)	0.0253 (6)	−0.0018 (5)
N1	0.0493 (10)	0.0379 (9)	0.0361 (8)	−0.0088 (7)	0.0252 (8)	−0.0071 (7)
N2	0.0437 (9)	0.0384 (8)	0.0333 (8)	−0.0090 (7)	0.0188 (7)	0.0005 (6)
C1	0.0448 (11)	0.0291 (9)	0.0438 (10)	0.0012 (8)	0.0199 (9)	−0.0017 (8)
C2	0.0428 (11)	0.0460 (12)	0.0497 (11)	0.0019 (9)	0.0266 (9)	−0.0013 (9)
C3	0.0494 (12)	0.0427 (11)	0.0549 (12)	−0.0112 (10)	0.0259 (10)	0.0050 (9)
C4	0.0572 (13)	0.0308 (10)	0.0576 (12)	−0.0045 (9)	0.0252 (11)	−0.0012 (9)
C5	0.0449 (11)	0.0349 (10)	0.0435 (10)	0.0010 (9)	0.0206 (9)	−0.0045 (8)
C6	0.0398 (10)	0.0326 (9)	0.0294 (8)	−0.0031 (8)	0.0150 (8)	−0.0008 (7)
C7	0.0379 (10)	0.0300 (9)	0.0338 (9)	0.0033 (8)	0.0165 (8)	0.0014 (7)
C8	0.0408 (11)	0.0433 (11)	0.0449 (11)	−0.0065 (9)	0.0177 (9)	−0.0050 (9)
C9	0.0563 (14)	0.0431 (12)	0.0725 (14)	−0.0106 (10)	0.0326 (12)	−0.0082 (10)
C10	0.0637 (15)	0.0638 (14)	0.0549 (13)	−0.0065 (12)	0.0283 (12)	0.0179 (11)
C11	0.0588 (13)	0.0536 (12)	0.0389 (10)	−0.0124 (10)	0.0247 (9)	0.0023 (9)

F1—C1	1.342 (2)	C3—C4	1.361 (3)
F2—C2	1.347 (2)	C4—H4	0.9300
F3—C3	1.349 (2)	C4—C5	1.383 (3)
O1—C9	1.424 (2)	C5—H5	0.9300
O1—C10	1.413 (3)	C5—C6	1.384 (2)
O2—C7	1.232 (2)	C8—H8A	0.9700
N1—C6	1.409 (2)	C8—H8B	0.9700
N1—C7	1.383 (2)	C8—C9	1.504 (3)
N1—H1	0.843 (18)	C9—H9A	0.9700
N2—C7	1.349 (2)	C9—H9B	0.9700
N2—C8	1.459 (2)	C10—H10A	0.9700
N2—C11	1.455 (2)	C10—H10B	0.9700
C1—C2	1.374 (3)	C10—C11	1.508 (3)
C1—C6	1.382 (2)	C11—H11A	0.9700
C2—C3	1.368 (3)	C11—H11B	0.9700
C10—O1—C9	109.68 (15)	O2—C7—N2	122.31 (16)
C6—N1—H1	116.2 (13)	N2—C7—N1	116.05 (15)
C7—N1—C6	121.05 (14)	N2—C8—H8A	109.5
C7—N1—H1	118.2 (13)	N2—C8—H8B	109.5
C7—N2—C8	119.83 (14)	N2—C8—C9	110.94 (15)
C7—N2—C11	123.95 (15)	H8A—C8—H8B	108.0
C11—N2—C8	113.93 (15)	C9—C8—H8A	109.5
F1—C1—C2	118.37 (17)	C9—C8—H8B	109.5
F1—C1—C6	120.70 (16)	O1—C9—C8	111.42 (17)
C2—C1—C6	120.91 (17)	O1—C9—H9A	109.3
F2—C2—C1	119.96 (17)	O1—C9—H9B	109.3
F2—C2—C3	120.24 (18)	C8—C9—H9A	109.3
C3—C2—C1	119.78 (18)	C8—C9—H9B	109.3
F3—C3—C2	118.52 (18)	H9A—C9—H9B	108.0
F3—C3—C4	120.61 (18)	O1—C10—H10A	109.3
C4—C3—C2	120.83 (18)	O1—C10—H10B	109.3
C3—C4—H4	120.4	O1—C10—C11	111.65 (17)
C3—C4—C5	119.28 (18)	H10A—C10—H10B	108.0
C5—C4—H4	120.4	C11—C10—H10A	109.3
C4—C5—H5	119.5	C11—C10—H10B	109.3
C4—C5—C6	121.08 (18)	N2—C11—C10	109.20 (16)
C6—C5—H5	119.5	N2—C11—H11A	109.8
C1—C6—N1	120.74 (15)	N2—C11—H11B	109.8
C1—C6—C5	117.99 (17)	C10—C11—H11A	109.8
C5—C6—N1	121.17 (16)	C10—C11—H11B	109.8
O2—C7—N1	121.59 (16)	H11A—C11—H11B	108.3

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.843 (18)	2.120 (19)	2.9306 (19)	161.2 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.843 (18)	2.120 (19)	2.9306 (19)	161.2 (17)

Symmetry code: (i) .