1-(2-Amino-5-chloro­phen­yl)-2,2,2-tri­fluoro­ethan-1-one

In the title compound, C₈H₅ClF₃NO, the F—C—C=O grouping shows a syn conformation [torsion angle = 1.1 (3)°] and an intra­molecular N—H...O hydrogen bond generates an S(6) ring. In the crystal, N—H...F and N—H...O hydrogen bonds link the mol­ecules into [010] chains.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.113
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -0.749 Report
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1-(2-Amino-5-chlorophenyl)-2,2,2-trifluoroethan-1-one

Crystal data

C8H5ClF3NO	F(000) = 448
Mr = 223.58	Dx = 1.759 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.7307 (16) Å	Cell parameters from 2386 reflections
b = 9.0363 (12) Å	θ = 2.8–27.3°
c = 7.4742 (9) Å	µ = 0.46 mm^−1
β = 100.924 (4)°	T = 120 K
V = 844.24 (19) Å^3	Block, yellow
Z = 4	0.20 × 0.10 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer	1374 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.091
Absorption correction: multi-scan (SADABS; Bruker, 2005)	θmax = 27.5°, θmin = 3.3°
Tmin = 0.304, Tmax = 0.746	h = −16→15
8037 measured reflections	k = −11→11
1934 independent reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0262P)^2 + 0.5023P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1934 reflections	Δρmax = 0.37 e Å^−3
135 parameters	Δρmin = −0.32 e Å^−3
0 restraints

Special details

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. All H atoms were positioned geometrically and refined using a riding model.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.52355 (5)	0.71433 (7)	0.54712 (9)	0.0274 (2)
F2	0.19882 (12)	0.37800 (16)	0.46110 (19)	0.0281 (4)
F3	0.26469 (12)	0.36210 (16)	0.7480 (2)	0.0283 (4)
F1	0.09924 (13)	0.31042 (16)	0.6487 (2)	0.0293 (4)
O1	0.05780 (14)	0.5844 (2)	0.6915 (2)	0.0257 (4)
N1	0.0944 (2)	0.8744 (3)	0.6703 (3)	0.0273 (5)
C2	0.1916 (2)	0.8337 (3)	0.6426 (3)	0.0202 (5)
C7	0.1467 (2)	0.5662 (3)	0.6533 (3)	0.0197 (5)
C6	0.3249 (2)	0.6482 (3)	0.5988 (3)	0.0198 (5)
H6	0.345180	0.547756	0.589568	0.024*
C1	0.2214 (2)	0.6819 (3)	0.6294 (3)	0.0183 (5)
C4	0.3678 (2)	0.9071 (3)	0.5960 (3)	0.0242 (6)
H4	0.417990	0.983013	0.586013	0.029*
C8	0.1775 (2)	0.4030 (3)	0.6273 (3)	0.0226 (6)
C5	0.3962 (2)	0.7580 (3)	0.5822 (3)	0.0206 (5)
C3	0.2680 (2)	0.9429 (3)	0.6238 (3)	0.0249 (6)
H3	0.249430	1.044290	0.630777	0.030*
H1A	0.051 (2)	0.814 (3)	0.689 (4)	0.022 (8)*
H1B	0.084 (3)	0.961 (4)	0.684 (4)	0.045 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0210 (4)	0.0319 (4)	0.0306 (4)	−0.0025 (3)	0.0077 (3)	−0.0007 (3)
F2	0.0373 (10)	0.0229 (8)	0.0252 (8)	−0.0002 (7)	0.0089 (7)	−0.0039 (6)
F3	0.0246 (8)	0.0256 (8)	0.0320 (8)	0.0029 (6)	−0.0012 (7)	0.0063 (7)
F1	0.0278 (9)	0.0211 (8)	0.0395 (9)	−0.0051 (6)	0.0076 (7)	0.0037 (7)
O1	0.0215 (10)	0.0261 (10)	0.0300 (10)	−0.0009 (8)	0.0064 (8)	0.0000 (8)
N1	0.0274 (14)	0.0222 (14)	0.0338 (13)	0.0007 (11)	0.0096 (11)	−0.0012 (11)
C2	0.0233 (14)	0.0234 (12)	0.0135 (11)	0.0016 (11)	0.0027 (10)	0.0002 (10)
C7	0.0202 (13)	0.0218 (13)	0.0163 (11)	0.0003 (10)	0.0018 (10)	0.0006 (10)
C6	0.0237 (14)	0.0194 (13)	0.0157 (11)	0.0007 (10)	0.0027 (10)	0.0005 (10)
C1	0.0202 (13)	0.0198 (12)	0.0145 (11)	0.0000 (10)	0.0021 (10)	−0.0006 (9)
C4	0.0288 (15)	0.0229 (13)	0.0212 (13)	−0.0059 (11)	0.0053 (11)	0.0013 (10)
C8	0.0228 (14)	0.0228 (13)	0.0221 (12)	−0.0017 (11)	0.0041 (11)	0.0010 (10)
C5	0.0211 (13)	0.0258 (13)	0.0151 (12)	−0.0007 (11)	0.0039 (10)	−0.0003 (10)
C3	0.0341 (16)	0.0168 (13)	0.0251 (13)	0.0001 (11)	0.0086 (12)	−0.0004 (10)

Geometric parameters (Å, º)

Cl1—C5	1.736 (3)	C7—C1	1.447 (3)
F2—C8	1.340 (3)	C7—C8	1.548 (3)
F3—C8	1.343 (3)	C6—C5	1.366 (4)
F1—C8	1.334 (3)	C6—C1	1.413 (3)
O1—C7	1.229 (3)	C6—H6	0.9500
N1—C2	1.344 (3)	C4—C3	1.364 (4)
N1—H1A	0.81 (3)	C4—C5	1.404 (4)
N1—H1B	0.81 (4)	C4—H4	0.9500
C2—C3	1.411 (4)	C3—H3	0.9500
C2—C1	1.432 (3)
C2—N1—H1A	121 (2)	C3—C4—C5	119.9 (2)
C2—N1—H1B	117 (2)	C3—C4—H4	120.0
H1A—N1—H1B	121 (3)	C5—C4—H4	120.0
N1—C2—C3	119.7 (2)	F1—C8—F2	107.0 (2)
N1—C2—C1	122.4 (2)	F1—C8—F3	106.72 (19)
C3—C2—C1	117.9 (2)	F2—C8—F3	106.9 (2)
O1—C7—C1	126.0 (2)	F1—C8—C7	111.7 (2)
O1—C7—C8	115.0 (2)	F2—C8—C7	112.2 (2)
C1—C7—C8	119.0 (2)	F3—C8—C7	112.0 (2)
C5—C6—C1	121.0 (2)	C6—C5—C4	120.3 (2)
C5—C6—H6	119.5	C6—C5—Cl1	120.3 (2)
C1—C6—H6	119.5	C4—C5—Cl1	119.3 (2)
C6—C1—C2	119.0 (2)	C4—C3—C2	121.9 (2)
C6—C1—C7	121.3 (2)	C4—C3—H3	119.1
C2—C1—C7	119.7 (2)	C2—C3—H3	119.1
C5—C6—C1—C2	0.1 (3)	O1—C7—C8—F2	121.2 (2)
C5—C6—C1—C7	−177.9 (2)	C1—C7—C8—F2	−58.0 (3)
N1—C2—C1—C6	179.5 (2)	O1—C7—C8—F3	−118.6 (2)
C3—C2—C1—C6	0.1 (3)	C1—C7—C8—F3	62.2 (3)
N1—C2—C1—C7	−2.4 (4)	C1—C6—C5—C4	0.2 (4)
C3—C2—C1—C7	178.1 (2)	C1—C6—C5—Cl1	179.28 (18)
O1—C7—C1—C6	175.3 (2)	C3—C4—C5—C6	−0.8 (4)
C8—C7—C1—C6	−5.6 (3)	C3—C4—C5—Cl1	−179.91 (19)
O1—C7—C1—C2	−2.7 (4)	C5—C4—C3—C2	1.1 (4)
C8—C7—C1—C2	176.4 (2)	N1—C2—C3—C4	179.8 (2)
O1—C7—C8—F1	1.1 (3)	C1—C2—C3—C4	−0.7 (4)
C1—C7—C8—F1	−178.2 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.81 (3)	2.07 (3)	2.672 (3)	131 (3)
N1—H1A···F1^i	0.81 (3)	2.45 (3)	3.084 (3)	136 (3)
N1—H1B···O1^i	0.81 (4)	2.45 (3)	3.030 (3)	130 (3)

Symmetry code: (i) −x, y+1/2, −z+3/2.