4-(Morpholin-4-yl)-3-(trifluoro-meth-yl)-benzonitrile.

In the title benzonitrile compound, C(12)H(11)F(3)N(2)O, an intra-molecular C-H⋯F hydrogen bond generates an S(7) ring motif. The trifluoro-methyl group is disordered over two orientations with a refined occupancy ratio of 0.549 (16):0.451 (16). The morpholine ring adopts a chair conformation. The benzene ring and mean plane of the morpholine ring make a dihedral angle of 58.04 (10)° with each other. In the crystal, mol-ecules are connected by inter-molecular C-H⋯F and C-H⋯O inter-actions to form R(2) (2)(8) ring motifs. These inter-actions also link the mol-ecules into chains parallel to the [10[Formula: see text]] direction.

Related literature

For general background and applications of materials related to the title compound, see: Raparti et al. (2009 ▶). For the synthesis of fluvoxamine, see: Schareina et al. (2004 ▶). For synthesis of the title compound, see: Kleemann et al. (2001 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For definition of puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C12H11F3N2O

M = 256.23

Monoclinic,

a = 12.7003 (12) Å

b = 6.8990 (7) Å

c = 13.3484 (13) Å

β = 91.668 (2)°

V = 1169.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 296 K

0.85 × 0.25 × 0.12 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.899, T max = 0.985

11929 measured reflections

3382 independent reflections

2399 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.132

S = 1.07

3382 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811020666/rz2604sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811020666/rz2604Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811020666/rz2604Isup3.cml

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

C12H11F3N2O	F(000) = 528
Mr = 256.23	Dx = 1.456 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3536 reflections
a = 12.7003 (12) Å	θ = 3.1–29.3°
b = 6.8990 (7) Å	µ = 0.13 mm−1
c = 13.3484 (13) Å	T = 296 K
β = 91.668 (2)°	Plate, colourless
V = 1169.1 (2) Å3	0.85 × 0.25 × 0.12 mm
Z = 4

Bruker APEX DUO CCD area-detector diffractometer	3382 independent reflections
Radiation source: fine-focus sealed tube	2399 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→17
Tmin = 0.899, Tmax = 0.985	k = −9→9
11929 measured reflections	l = −18→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.0566P)2 + 0.1831P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
3382 reflections	Δρmax = 0.25 e Å−3
192 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (2)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
F1	0.7836 (5)	0.4513 (6)	0.0784 (4)	0.0736 (12)	0.549 (16)
F2	0.8776 (5)	0.2468 (9)	0.1535 (5)	0.0737 (13)	0.549 (16)
F3	0.7289 (6)	0.3126 (14)	0.2091 (5)	0.102 (2)	0.549 (16)
F1B	0.7282 (13)	0.4501 (8)	0.1030 (7)	0.110 (3)	0.451 (16)
F2B	0.8734 (6)	0.301 (2)	0.1241 (10)	0.107 (3)	0.451 (16)
F3B	0.7507 (7)	0.2605 (15)	0.2204 (4)	0.090 (2)	0.451 (16)
O1	0.98647 (10)	0.34879 (18)	−0.21269 (9)	0.0691 (4)
N1	0.85532 (8)	0.17086 (16)	−0.07037 (8)	0.0412 (3)
N2	0.45173 (11)	−0.3350 (2)	0.12877 (13)	0.0742 (4)
C1	0.92779 (15)	0.0579 (2)	−0.12999 (16)	0.0747 (6)
H1A	0.8918	0.0116	−0.1905	0.090*
H1B	0.9527	−0.0536	−0.0919	0.090*
C2	1.01990 (16)	0.1842 (3)	−0.15715 (18)	0.0829 (7)
H2A	1.0570	0.2260	−0.0964	0.099*
H2B	1.0685	0.1093	−0.1964	0.099*
C3	0.91524 (13)	0.4581 (2)	−0.15705 (15)	0.0675 (5)
H3A	0.8916	0.5687	−0.1965	0.081*
H3B	0.9510	0.5067	−0.0970	0.081*
C4	0.82075 (12)	0.3401 (2)	−0.12777 (13)	0.0598 (4)
H4A	0.7746	0.4189	−0.0878	0.072*
H4B	0.7816	0.2990	−0.1875	0.072*
C5	0.77145 (9)	0.06434 (17)	−0.02829 (8)	0.0364 (3)
C6	0.72846 (11)	−0.0982 (2)	−0.07585 (10)	0.0487 (3)
H6A	0.7562	−0.1390	−0.1361	0.058*
C7	0.64609 (11)	−0.2008 (2)	−0.03650 (11)	0.0505 (3)
H7A	0.6187	−0.3087	−0.0699	0.061*
C8	0.60446 (10)	−0.14135 (19)	0.05332 (10)	0.0418 (3)
C9	0.64620 (9)	0.01808 (19)	0.10331 (9)	0.0394 (3)
H9A	0.6182	0.0571	0.1637	0.047*
C10	0.72972 (9)	0.12021 (17)	0.06375 (9)	0.0360 (3)
C11	0.77589 (11)	0.2827 (2)	0.12573 (11)	0.0481 (3)
C12	0.51905 (11)	−0.2485 (2)	0.09623 (11)	0.0517 (3)

	U11	U22	U33	U12	U13	U23
F1	0.100 (3)	0.0403 (11)	0.0802 (18)	−0.0085 (14)	−0.0012 (17)	−0.0078 (10)
F2	0.053 (2)	0.0799 (19)	0.086 (3)	−0.0015 (17)	−0.020 (2)	−0.0182 (16)
F3	0.085 (2)	0.134 (5)	0.090 (4)	−0.050 (2)	0.059 (2)	−0.073 (3)
F1B	0.175 (8)	0.0450 (17)	0.107 (4)	0.028 (3)	−0.034 (4)	−0.021 (2)
F2B	0.058 (3)	0.148 (7)	0.118 (6)	−0.054 (4)	0.036 (3)	−0.083 (5)
F3B	0.133 (5)	0.104 (4)	0.0318 (17)	−0.054 (3)	0.004 (2)	−0.013 (2)
O1	0.0764 (8)	0.0712 (7)	0.0617 (7)	−0.0107 (6)	0.0354 (6)	0.0108 (6)
N1	0.0425 (5)	0.0427 (5)	0.0392 (5)	−0.0004 (4)	0.0159 (4)	0.0028 (4)
N2	0.0601 (8)	0.0777 (10)	0.0852 (11)	−0.0232 (7)	0.0116 (7)	0.0158 (8)
C1	0.0833 (12)	0.0516 (9)	0.0924 (13)	0.0031 (8)	0.0588 (10)	0.0010 (8)
C2	0.0725 (11)	0.0692 (11)	0.1103 (16)	0.0081 (9)	0.0591 (11)	0.0188 (11)
C3	0.0664 (10)	0.0548 (9)	0.0829 (12)	−0.0047 (7)	0.0286 (9)	0.0168 (8)
C4	0.0516 (8)	0.0597 (9)	0.0687 (10)	−0.0008 (7)	0.0136 (7)	0.0229 (7)
C5	0.0377 (6)	0.0381 (6)	0.0337 (6)	−0.0008 (5)	0.0066 (4)	0.0022 (5)
C6	0.0578 (8)	0.0498 (7)	0.0391 (7)	−0.0086 (6)	0.0120 (6)	−0.0086 (5)
C7	0.0559 (8)	0.0448 (7)	0.0508 (8)	−0.0115 (6)	0.0041 (6)	−0.0066 (6)
C8	0.0362 (6)	0.0433 (6)	0.0461 (7)	−0.0038 (5)	0.0028 (5)	0.0078 (5)
C9	0.0361 (6)	0.0456 (6)	0.0368 (6)	0.0005 (5)	0.0074 (4)	0.0028 (5)
C10	0.0356 (6)	0.0380 (6)	0.0348 (6)	−0.0006 (4)	0.0058 (4)	−0.0012 (5)
C11	0.0506 (7)	0.0496 (7)	0.0447 (7)	−0.0063 (6)	0.0117 (6)	−0.0101 (6)
C12	0.0448 (7)	0.0528 (8)	0.0577 (8)	−0.0089 (6)	0.0026 (6)	0.0081 (6)

F1—C11	1.328 (4)	C3—C4	1.511 (2)
F2—C11	1.357 (6)	C3—H3A	0.9700
F3—C11	1.294 (5)	C3—H3B	0.9700
F1B—C11	1.335 (5)	C4—H4A	0.9700
F2B—C11	1.245 (7)	C4—H4B	0.9700
F3B—C11	1.321 (6)	C5—C6	1.3925 (18)
O1—C3	1.4064 (19)	C5—C10	1.4060 (16)
O1—C2	1.415 (2)	C6—C7	1.3794 (18)
N1—C5	1.4230 (14)	C6—H6A	0.9300
N1—C4	1.4573 (18)	C7—C8	1.3863 (19)
N1—C1	1.4597 (17)	C7—H7A	0.9300
N2—C12	1.1388 (18)	C8—C9	1.3840 (18)
C1—C2	1.511 (2)	C8—C12	1.4449 (18)
C1—H1A	0.9700	C9—C10	1.3902 (16)
C1—H1B	0.9700	C9—H9A	0.9300
C2—H2A	0.9700	C10—C11	1.5023 (18)
C2—H2B	0.9700
C3—O1—C2	109.97 (12)	C5—C6—H6A	119.0
C5—N1—C4	113.82 (10)	C6—C7—C8	119.37 (12)
C5—N1—C1	115.51 (11)	C6—C7—H7A	120.3
C4—N1—C1	109.04 (12)	C8—C7—H7A	120.3
N1—C1—C2	109.13 (14)	C9—C8—C7	120.10 (11)
N1—C1—H1A	109.9	C9—C8—C12	119.81 (12)
C2—C1—H1A	109.9	C7—C8—C12	120.08 (12)
N1—C1—H1B	109.9	C8—C9—C10	120.36 (11)
C2—C1—H1B	109.9	C8—C9—H9A	119.8
H1A—C1—H1B	108.3	C10—C9—H9A	119.8
O1—C2—C1	111.47 (17)	C9—C10—C5	120.27 (11)
O1—C2—H2A	109.3	C9—C10—C11	117.32 (11)
C1—C2—H2A	109.3	C5—C10—C11	122.33 (11)
O1—C2—H2B	109.3	F2B—C11—F3	118.8 (5)
C1—C2—H2B	109.3	F2B—C11—F3B	107.3 (6)
H2A—C2—H2B	108.0	F2B—C11—F1	79.4 (6)
O1—C3—C4	112.06 (14)	F3—C11—F1	108.2 (4)
O1—C3—H3A	109.2	F3B—C11—F1	125.4 (4)
C4—C3—H3A	109.2	F2B—C11—F1B	110.7 (4)
O1—C3—H3B	109.2	F3—C11—F1B	80.8 (4)
C4—C3—H3B	109.2	F3B—C11—F1B	101.4 (5)
H3A—C3—H3B	107.9	F3—C11—F2	104.7 (4)
N1—C4—C3	109.77 (13)	F3B—C11—F2	88.5 (5)
N1—C4—H4A	109.7	F1—C11—F2	101.9 (3)
C3—C4—H4A	109.7	F1B—C11—F2	129.9 (6)
N1—C4—H4B	109.7	F2B—C11—C10	116.0 (4)
C3—C4—H4B	109.7	F3—C11—C10	114.2 (3)
H4A—C4—H4B	108.2	F3B—C11—C10	109.8 (4)
C6—C5—C10	117.81 (11)	F1—C11—C10	115.1 (2)
C6—C5—N1	121.60 (11)	F1B—C11—C10	110.7 (3)
C10—C5—N1	120.59 (11)	F2—C11—C10	111.6 (3)
C7—C6—C5	122.07 (12)	N2—C12—C8	178.91 (18)
C7—C6—H6A	119.0
C5—N1—C1—C2	−172.23 (15)	C8—C9—C10—C5	1.04 (18)
C4—N1—C1—C2	58.1 (2)	C8—C9—C10—C11	−175.72 (12)
C3—O1—C2—C1	58.5 (2)	C6—C5—C10—C9	−1.85 (18)
N1—C1—C2—O1	−59.4 (2)	N1—C5—C10—C9	178.54 (11)
C2—O1—C3—C4	−57.5 (2)	C6—C5—C10—C11	174.75 (12)
C5—N1—C4—C3	172.24 (13)	N1—C5—C10—C11	−4.86 (18)
C1—N1—C4—C3	−57.19 (18)	C9—C10—C11—F2B	141.6 (9)
O1—C3—C4—N1	57.6 (2)	C5—C10—C11—F2B	−35.0 (9)
C4—N1—C5—C6	96.34 (15)	C9—C10—C11—F3	−2.1 (6)
C1—N1—C5—C6	−30.95 (19)	C5—C10—C11—F3	−178.8 (5)
C4—N1—C5—C10	−84.08 (15)	C9—C10—C11—F3B	19.9 (5)
C1—N1—C5—C10	148.64 (14)	C5—C10—C11—F3B	−156.8 (5)
C10—C5—C6—C7	1.4 (2)	C9—C10—C11—F1	−128.2 (4)
N1—C5—C6—C7	−178.98 (13)	C5—C10—C11—F1	55.1 (4)
C5—C6—C7—C8	−0.1 (2)	C9—C10—C11—F1B	−91.2 (8)
C6—C7—C8—C9	−0.7 (2)	C5—C10—C11—F1B	92.2 (8)
C6—C7—C8—C12	−179.22 (13)	C9—C10—C11—F2	116.3 (3)
C7—C8—C9—C10	0.27 (19)	C5—C10—C11—F2	−60.4 (3)
C12—C8—C9—C10	178.77 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···F3i	0.97	2.49	3.242 (5)	135.
C4—H4A···F1	0.97	2.23	2.909 (6)	126.
C9—H9A···O1ii	0.93	2.47	3.3588 (16)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯F3i	0.97	2.49	3.242 (5)	135
C4—H4A⋯F1	0.97	2.23	2.909 (6)	126
C9—H9A⋯O1ii	0.93	2.47	3.3588 (16)	160

Symmetry codes: (i) ; (ii) .