Methyl 4-(tri-fluoro-meth-yl)-1H-pyrrole-3-carboxyl-ate.

In the title compound, C7H6F3NO2, all the non-H atoms except for one of the F atoms lie on a crystallographic mirror plane. In the crystal, the mol-ecules are linked into inversion dimers by pairs of C-H⋯F inter-actions, forming R 2 (2)(10) loops. These dimers are connected into C(6) chains along [001] through N-H⋯O hydrogen bonds. Aromatic π-π stacking inter-actions [centroid-centroid separation = 3.8416 (10) A°] connect the mol-ecules into a three-dimensional network.

Related literature

For background to the pharmacological activity of pyrrole derivatives, see: Toja et al. (1987 ▶); Muchowski et al. (1985 ▶); Dannhardt et al. (2000 ▶); Burnham et al. (1998 ▶); Krowicki et al. (1988 ▶).

Experimental

Crystal data

C7H6F3NO2

M = 193.13

Monoclinic,

a = 16.643 (2) Å

b = 7.1118 (10) Å

c = 6.9618 (11) Å

β = 98.903 (7)°

V = 814.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 293 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.969

3752 measured reflections

707 independent reflections

645 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.180

S = 1.09

707 reflections

81 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.32 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S160053681302549X/hb7136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302549X/hb7136Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302549X/hb7136Isup3.cml

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

C7H6F3NO2	prism
Mr = 193.13	Dx = 1.576 Mg m−3
Monoclinic, C2/m	Melting point: 405 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 16.643 (2) Å	Cell parameters from 645 reflections
b = 7.1118 (10) Å	θ = 3.0–24.4°
c = 6.9618 (11) Å	µ = 0.16 mm−1
β = 98.903 (7)°	T = 293 K
V = 814.1 (2) Å3	Prism, colourless
Z = 4	0.24 × 0.22 × 0.20 mm
F(000) = 392

Bruker APEXII CCD diffractometer	707 independent reflections
Radiation source: fine-focus sealed tube	645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 1.08 pixels mm-1	θmax = 24.4°, θmin = 3.0°
ω scans	h = −19→19
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −8→8
Tmin = 0.963, Tmax = 0.969	l = −3→7
3752 measured reflections

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)] = 0.065	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.1299P)2 + 0.3175P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
707 reflections	Δρmax = 0.37 e Å−3
81 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.08 (2)
Primary atom site location: structure-invariant direct methods

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	Occ. (<1)
H	0.275 (3)	0.0000	−0.341 (8)	0.073 (13)*
C1	0.0515 (2)	0.0000	0.2701 (6)	0.0765 (12)
H1A	0.0456	0.1254	0.3171	0.115*	0.50
H1B	0.0701	−0.0816	0.3777	0.115*	0.50
H1C	0.0000	−0.0438	0.2042	0.115*	0.50
C2	0.18890 (17)	0.0000	0.2149 (4)	0.0436 (9)
C3	0.24211 (16)	0.0000	0.0673 (4)	0.0391 (8)
C4	0.21641 (19)	0.0000	−0.1280 (4)	0.0480 (8)
H4	0.1625	0.0000	−0.1881	0.058*
C5	0.3504 (2)	0.0000	−0.0863 (5)	0.0563 (10)
H5	0.4034	0.0000	−0.1137	0.068*
C6	0.32889 (16)	0.0000	0.0952 (4)	0.0443 (8)
C7	0.38690 (18)	0.0000	0.2762 (5)	0.0544 (9)
F1	0.46353 (14)	0.0000	0.2439 (4)	0.1048 (12)
F2	0.38017 (10)	0.1475 (2)	0.3904 (2)	0.0853 (8)
N	0.28189 (18)	0.0000	−0.2200 (5)	0.0587 (9)
O1	0.20994 (15)	0.0000	0.3872 (3)	0.0718 (9)
O2	0.11034 (12)	0.0000	0.1358 (3)	0.0586 (8)

	U11	U22	U33	U12	U13	U23
C1	0.057 (2)	0.116 (3)	0.058 (3)	0.000	0.0154 (17)	0.000
C2	0.0503 (16)	0.0517 (15)	0.026 (2)	0.000	−0.0038 (11)	0.000
C3	0.0478 (15)	0.0422 (13)	0.0235 (19)	0.000	−0.0066 (11)	0.000
C4	0.0574 (17)	0.0589 (16)	0.0237 (19)	0.000	−0.0065 (12)	0.000
C5	0.0570 (17)	0.0708 (19)	0.042 (2)	0.000	0.0092 (14)	0.000
C6	0.0491 (16)	0.0483 (14)	0.0331 (18)	0.000	−0.0007 (11)	0.000
C7	0.0481 (16)	0.0667 (17)	0.045 (2)	0.000	−0.0052 (13)	0.000
F1	0.0486 (13)	0.185 (3)	0.076 (2)	0.000	−0.0056 (11)	0.000
F2	0.0959 (13)	0.0903 (13)	0.0570 (14)	−0.0019 (7)	−0.0278 (8)	−0.0240 (7)
N	0.077 (2)	0.0781 (18)	0.020 (2)	0.000	0.0034 (13)	0.000
O1	0.0645 (15)	0.125 (2)	0.0230 (17)	0.000	−0.0013 (10)	0.000
O2	0.0470 (13)	0.0914 (16)	0.0352 (16)	0.000	−0.0006 (9)	0.000

C1—O2	1.455 (4)	C4—H4	0.9300
C1—H1A	0.9600	C5—N	1.356 (5)
C1—H1B	0.9600	C5—C6	1.366 (5)
C1—H1C	0.9600	C5—H5	0.9300
C2—O1	1.196 (4)	C6—C7	1.464 (5)
C2—O2	1.338 (4)	C7—F1	1.329 (4)
C2—C3	1.457 (4)	C7—F2i	1.332 (3)
C3—C4	1.360 (4)	C7—F2	1.332 (3)
C3—C6	1.427 (4)	N—H	0.84 (5)
C4—N	1.347 (4)
O2—C1—H1A	109.5	N—C5—H5	125.6
O2—C1—H1B	109.5	C6—C5—H5	125.6
H1A—C1—H1B	109.5	C5—C6—C3	106.2 (3)
O2—C1—H1C	109.5	C5—C6—C7	124.3 (3)
H1A—C1—H1C	109.5	C3—C6—C7	129.5 (3)
H1B—C1—H1C	109.5	F1—C7—F2i	105.81 (19)
O1—C2—O2	121.9 (3)	F1—C7—F2	105.81 (19)
O1—C2—C3	126.3 (3)	F2i—C7—F2	104.0 (3)
O2—C2—C3	111.8 (3)	F1—C7—C6	112.2 (3)
C4—C3—C6	106.9 (3)	F2i—C7—C6	114.12 (17)
C4—C3—C2	125.0 (3)	F2—C7—C6	114.12 (17)
C6—C3—C2	128.1 (3)	C4—N—C5	109.3 (3)
N—C4—C3	108.8 (3)	C4—N—H	119 (3)
N—C4—H4	125.6	C5—N—H	131 (3)
C3—C4—H4	125.6	C2—O2—C1	116.6 (3)
N—C5—C6	108.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···O1ii	0.83 (6)	2.03 (5)	2.810 (4)	156
C5—H5···F1iii	0.93	2.52	3.442 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯O1i	0.83 (6)	2.03 (5)	2.810 (4)	156
C5—H5⋯F1ii	0.93	2.52	3.442 (4)	171

Symmetry codes: (i) ; (ii) .