Methyl 5-chloro-2-{[(trifluoro­methyl)­sulfonyl]amino}benzoate

The title compound [systematic name: methyl 5-chloro-2-(trifluoro­methyl­sulfonamido)benzoate], C₉H₇ClF₃NO₄S, is a novel acaricide commonly named amido­flumet. The orientations of two side chains are such that the sulfonamide H atom and the carbonyl O atom of the ester substituent are coplanar with the aromatic ring, forming an intra­molecular N—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.105
• wR factor = 0.284
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.91

Author Response: ... The crystal of amidoflumet obtained was well grown but a little fragile and the structural anisotropy was observed. These characters are likely to be intrinsic to amidoflumet molecule because the major inter-molecular interaction does not exist along C-axis. Therefore, the diffraction spots observed were rather broad and the number of them was a little smaller, but it was enough to obtain the crystal structure.

Alert level B
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.66
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         11

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.178     0.616
            Tmin(prime) and Tmax expected:      0.205     0.616
            RR(prime) =      0.870
            Please check that your absorption correction is appropriate.
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           68.24
           From the CIF: _diffrn_reflns_theta_full          68.24
           From the CIF: _reflns_number_total               2073
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         2268
           Completeness (_total/calc)             91.40%
RFACG01_ALERT_3_C  The value of the R factor is > 0.10
            R factor given   0.105
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.284
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.127
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.91
PLAT084_ALERT_2_C High R2 Value ..................................       0.28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9

   1 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: CrystalStructure.

Methyl 5-chloro-2-(trifluoromethylsulfonamido)benzoate

Crystal data

C9H7ClF3NO4S	Z = 2
Mr = 317.67	F(000) = 320.00
Triclinic, P1	Dx = 1.711 Mg m^−3
Hall symbol: -P 1	Melting point: 356 K
a = 5.341 (2) Å	Cu Kα radiation, λ = 1.5418 Å
b = 9.887 (1) Å	Cell parameters from 3856 reflections
c = 11.754 (3) Å	θ = 3.8–66.8°
α = 85.212 (9)°	µ = 4.84 mm^−1
β = 85.47 (1)°	T = 296 K
γ = 88.939 (6)°	Block, colorless
V = 616.5 (3) Å^3	0.30 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	1398 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.127
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.178, Tmax = 0.616	k = −10→10
12598 measured reflections	l = −14→14
2073 independent reflections

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.105	w = 1/[σ^2(Fo^2) + (0.1063P)^2 + 1.5441P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.284	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.36 e Å^−3
2073 reflections	Δρmin = −0.35 e Å^−3
177 parameters

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 3.0 σ(F²). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Cl1	0.8261 (5)	0.3175 (2)	0.6298 (2)	0.0859 (8)
S1	0.0020 (4)	0.1370 (2)	0.2240 (2)	0.0705 (7)
F1	0.323 (1)	0.1003 (6)	0.0536 (4)	0.099 (2)
F2	0.111 (1)	−0.0741 (5)	0.1131 (5)	0.108 (2)
F3	0.407 (1)	−0.0144 (5)	0.2087 (4)	0.094 (2)
O1	0.393 (1)	0.4687 (5)	0.1514 (5)	0.077 (2)
O2	0.740 (1)	0.5343 (6)	0.2210 (5)	0.092 (2)
O3	−0.086 (1)	0.0537 (6)	0.3218 (5)	0.089 (2)
O4	−0.159 (1)	0.1923 (6)	0.1418 (5)	0.084 (2)
N1	0.166 (1)	0.2577 (7)	0.2573 (6)	0.072 (2)
C1	0.639 (2)	0.2953 (8)	0.5191 (6)	0.066 (2)
C2	0.460 (2)	0.1950 (8)	0.5315 (7)	0.071 (2)
C3	0.307 (2)	0.1806 (8)	0.4457 (7)	0.073 (2)
C4	0.329 (1)	0.2644 (7)	0.3467 (6)	0.060 (2)
C5	0.511 (1)	0.3670 (7)	0.3317 (6)	0.058 (2)
C6	0.663 (2)	0.3799 (7)	0.4203 (6)	0.065 (2)
C7	0.539 (2)	0.4598 (7)	0.2265 (6)	0.063 (2)
C8	0.781 (2)	0.631 (1)	0.1217 (9)	0.125 (4)
C9	0.227 (2)	0.0309 (8)	0.1457 (7)	0.074 (2)
H1	0.4429	0.1362	0.5998	0.085*
H2	0.1837	0.1116	0.4547	0.088*
H3	0.7862	0.4488	0.4125	0.078*
H4	0.7968	0.5828	0.0536	0.150*
H5	0.9301	0.6795	0.1273	0.150*
H6	0.6408	0.6927	0.1183	0.150*
H7	0.18 (2)	0.304 (9)	0.200 (7)	0.08 (3)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.109 (2)	0.087 (2)	0.066 (1)	−0.000 (1)	−0.025 (1)	−0.011 (1)
S1	0.073 (1)	0.070 (1)	0.070 (1)	−0.013 (1)	−0.008 (1)	−0.0100 (9)
F1	0.115 (4)	0.103 (4)	0.074 (3)	0.009 (3)	0.004 (3)	0.001 (3)
F2	0.138 (5)	0.076 (3)	0.118 (4)	−0.020 (3)	−0.031 (4)	−0.028 (3)
F3	0.103 (4)	0.088 (3)	0.092 (3)	0.014 (3)	−0.028 (3)	−0.003 (3)
O1	0.095 (4)	0.070 (3)	0.065 (3)	−0.014 (3)	−0.021 (3)	0.007 (3)
O2	0.124 (5)	0.078 (4)	0.073 (4)	−0.035 (4)	−0.028 (3)	0.019 (3)
O3	0.097 (4)	0.095 (4)	0.072 (4)	−0.035 (3)	0.004 (3)	−0.006 (3)
O4	0.072 (3)	0.098 (4)	0.087 (4)	−0.006 (3)	−0.027 (3)	−0.007 (3)
N1	0.088 (5)	0.065 (4)	0.063 (4)	−0.013 (3)	−0.017 (4)	−0.004 (3)
C1	0.089 (6)	0.058 (5)	0.052 (4)	0.013 (4)	−0.013 (4)	−0.013 (3)
C2	0.087 (6)	0.069 (5)	0.055 (4)	−0.014 (4)	0.002 (4)	0.001 (3)
C3	0.097 (6)	0.059 (5)	0.064 (5)	−0.018 (4)	−0.008 (4)	0.000 (4)
C4	0.067 (4)	0.056 (4)	0.059 (4)	0.000 (3)	−0.004 (3)	−0.013 (3)
C5	0.069 (4)	0.047 (4)	0.058 (4)	−0.010 (3)	0.001 (3)	−0.010 (3)
C6	0.091 (5)	0.051 (4)	0.055 (4)	−0.002 (4)	−0.010 (4)	−0.016 (3)
C7	0.086 (5)	0.050 (4)	0.055 (4)	−0.007 (4)	−0.008 (4)	−0.006 (3)
C8	0.17 (1)	0.108 (8)	0.095 (7)	−0.049 (8)	−0.042 (7)	0.039 (6)
C9	0.092 (6)	0.062 (5)	0.069 (5)	−0.005 (4)	−0.017 (4)	−0.002 (4)

Geometric parameters (Å, º)

Cl1—C1	1.731 (8)	C2—C3	1.37 (1)
S1—O3	1.411 (6)	C3—C4	1.37 (1)
S1—O4	1.412 (6)	C4—C5	1.41 (1)
S1—N1	1.586 (8)	C5—C6	1.39 (1)
S1—C9	1.826 (9)	C5—C7	1.476 (9)
F1—C9	1.306 (9)	C9—S1	1.826 (9)
F2—C9	1.32 (1)	N1—H7	0.78 (8)
F3—C9	1.31 (1)	C2—H1	0.9500
O1—C7	1.22 (1)	C3—H2	0.9500
O2—C7	1.31 (1)	C6—H3	0.9500
O2—C8	1.45 (1)	C8—H4	0.9500
N1—C4	1.42 (1)	C8—H5	0.9500
C1—C2	1.38 (1)	C8—H6	0.9500
C1—C6	1.37 (1)
Cl1—C1—C2	120.1 (6)	C6—C1—C2	119.7 (7)
Cl1—C1—C6	120.2 (6)	C1—C6—C5	121.4 (7)
O4—S1—O3	122.6 (4)	C2—C3—C4	120.7 (8)
N1—S1—O3	111.3 (4)	C3—C4—C5	120.4 (7)
C9—S1—O3	104.9 (4)	C4—C5—C7	121.9 (7)
N1—S1—O4	107.1 (4)	C4—C5—C6	117.7 (6)
C9—S1—O4	105.1 (4)	C7—C5—C6	120.4 (6)
C9—S1—N1	104.1 (4)	S1—N1—H7	102 (6)
S1—N1—C4	131.0 (6)	O2—C8—H4	109.4691
S1—C9—F1	109.6 (6)	O2—C8—H5	109.4700
S1—C9—F2	109.5 (6)	O2—C8—H6	109.4653
S1—C9—F3	111.7 (6)	H7—N1—C4	121 (6)
F1—C9—F2	107.7 (7)	C1—C2—H1	119.9872
F1—C9—F3	109.8 (7)	C1—C6—H3	119.2864
F2—C9—F3	108.4 (7)	C2—C3—H2	119.6463
O1—C7—O2	122.2 (6)	H1—C2—C3	119.9873
O1—C7—C5	125.0 (7)	H2—C3—C4	119.6466
O2—C7—C5	112.8 (7)	C5—C6—H3	119.2867
C8—O2—C7	116.8 (7)	H5—C8—H4	109.4732
N1—C4—C5	116.8 (6)	H6—C8—H4	109.4777
N1—C4—C3	122.7 (7)	H6—C8—H5	109.4721
C1—C2—C3	120.0 (7)
O3—S1—N1—C4	33.1 (8)	C6—C1—C2—C3	0 (1)
O4—S1—N1—C4	169.7 (7)	Cl1—C1—C6—C5	−178.1 (6)
C9—S1—N1—C4	−79.3 (7)	C2—C1—C6—C5	−0.3 (9)
O3—S1—C9—F1	−179.0 (5)	C1—C2—C3—C4	0 (1)
O3—S1—C9—F2	63.0 (6)	C2—C3—C4—N1	−176.7 (7)
O3—S1—C9—F3	−57.2 (6)	C2—C3—C4—C5	0 (1)
O4—S1—C9—F1	50.5 (7)	N1—C4—C5—C6	176.6 (7)
O4—S1—C9—F2	−67.5 (6)	N1—C4—C5—C7	−2 (1)
O4—S1—C9—F3	172.3 (5)	C3—C4—C5—C6	0 (1)
N1—S1—C9—F1	−62.0 (6)	C3—C4—C5—C7	−179.5 (7)
N1—S1—C9—F2	−180.0 (4)	C4—C5—C6—C1	0 (1)
N1—S1—C9—F3	59.9 (6)	C7—C5—C6—C1	179.6 (7)
C8—O2—C7—O1	0 (1)	C4—C5—C7—O1	9 (1)
C8—O2—C7—C5	−178.9 (6)	C4—C5—C7—O2	−170.4 (7)
S1—N1—C4—C3	−24 (1)	C6—C5—C7—O1	−169.3 (7)
S1—N1—C4—C5	158.8 (7)	C6—C5—C7—O2	10 (1)
Cl1—C1—C2—C3	177.8 (7)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O1	0.78 (8)	2.01 (8)	2.606 (9)	132 (8)