Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-fluoro­phen­yl)-N-isopropyl-2-(methyl­sulfon­yl)acetamide

In the title compound, which is related to the herbicide flufenacet, the amide group and fluoro­benzene ring are almost perpendicular. A short O...π contact is observed in the crystal.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.031
• wR factor = 0.079
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report

Alert level G
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          1 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          5 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          3 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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
   3 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: APEX3 (Bruker, 2016); cell refinement: APEX3 (Bruker, 2016); data reduction: APEX3 (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2019/2 (Sheldrick, 2015b); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and CrystalExplorer (Spackman et al., 2021); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

N-(4-Fluorophenyl)-2-(methylsulfonyl)-N-(propan-2-yl)acetamide

Crystal data

C12H16FNO3S	F(000) = 576
Mr = 273.32	Dx = 1.381 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9530 (3) Å	Cell parameters from 9889 reflections
b = 8.7657 (2) Å	θ = 2.8–27.5°
c = 11.7723 (3) Å	µ = 0.26 mm^−1
β = 100.457 (1)°	T = 90 K
V = 1314.45 (5) Å^3	Rounded plate, colourless
Z = 4	0.32 × 0.31 × 0.09 mm

Data collection

Bruker D8 Venture dual source diffractometer	3010 independent reflections
Radiation source: microsource	2678 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	Rint = 0.030
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −16→16
Tmin = 0.833, Tmax = 0.971	k = −11→11
22801 measured reflections	l = −15→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: difference Fourier map
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0327P)^2 + 0.7883P] where P = (Fo^2 + 2Fc^2)/3
3010 reflections	(Δ/σ)max = 0.001
166 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. The crystal was mounted using polyisobutene oil on the tip of a fine glass fibre, which was fastened in a copper mounting pin with electrical solder. It was placed directly into the cold gas stream of a liquid-nitrogen based cryostat (Hope, 1994; Parkin & Hope, 1998).

Diffraction data were collected with the crystal at 90K, which is standard practice in this laboratory for the majority of flash-cooled crystals.

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 progress was checked using Platon (Spek, 2020) and by an R-tensor (Parkin, 2000). The final model was further checked with the IUCr utility checkCIF.

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

	x	y	z	Uiso*/Ueq
S1	0.54145 (2)	0.29322 (3)	0.38570 (3)	0.01394 (9)
F1	0.77308 (7)	0.83954 (10)	0.77262 (8)	0.0265 (2)
C1	0.70051 (10)	0.18349 (15)	0.54790 (11)	0.0153 (3)
N1	0.78957 (9)	0.26470 (13)	0.58233 (10)	0.0169 (2)
O1	0.69978 (7)	0.04745 (11)	0.52217 (8)	0.0193 (2)
C2	0.59691 (10)	0.26923 (15)	0.53498 (11)	0.0154 (3)
H2A	0.608749	0.370378	0.572495	0.018*
H2AB	0.547429	0.211700	0.573787	0.018*
O2	0.62454 (7)	0.33486 (11)	0.32511 (8)	0.0208 (2)
O3	0.45431 (7)	0.39662 (11)	0.38023 (8)	0.0201 (2)
C3	0.49181 (11)	0.11358 (15)	0.33711 (12)	0.0208 (3)
H3A	0.459299	0.120203	0.255330	0.031*
H3B	0.439182	0.081074	0.382298	0.031*
H3C	0.549247	0.039248	0.346600	0.031*
C9	0.7902 (1)	0.68848 (16)	0.61179 (12)	0.0191 (3)
H9	0.794529	0.777562	0.566931	0.023*
C8	0.79425 (10)	0.54409 (16)	0.56408 (12)	0.0188 (3)
H8	0.801145	0.533426	0.485496	0.023*
C7	0.7882 (1)	0.41507 (15)	0.63150 (11)	0.0154 (3)
C6	0.97208 (12)	0.2845 (2)	0.54665 (14)	0.0295 (3)
H6A	1.036051	0.225348	0.545252	0.044*
H6B	0.988878	0.372611	0.597886	0.044*
H6C	0.943028	0.319875	0.468411	0.044*
C5	0.93224 (12)	0.1303 (2)	0.71320 (14)	0.0309 (4)
H5A	0.877506	0.070798	0.740427	0.046*
H5B	0.950692	0.218725	0.763798	0.046*
H5C	0.994531	0.066468	0.714444	0.046*
C4	0.89195 (10)	0.18467 (16)	0.59065 (13)	0.0216 (3)
H4	0.880049	0.092462	0.539939	0.026*
C10	0.77975 (10)	0.69895 (15)	0.72594 (12)	0.0180 (3)
C11	0.77354 (10)	0.57396 (16)	0.79470 (11)	0.0174 (3)
H11	0.766284	0.585728	0.873082	0.021*
C12	0.77814 (10)	0.42986 (15)	0.74673 (11)	0.0162 (3)
H12	0.774416	0.341486	0.792531	0.019*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01361 (16)	0.01232 (15)	0.01522 (16)	0.00096 (11)	0.00086 (11)	−0.00046 (11)
F1	0.0312 (5)	0.0167 (4)	0.0308 (5)	−0.0009 (3)	0.0033 (4)	−0.0072 (3)
C1	0.0176 (6)	0.0165 (6)	0.0114 (6)	0.0028 (5)	0.0012 (5)	0.0006 (5)
N1	0.0158 (5)	0.0159 (5)	0.0179 (5)	0.0033 (4)	0.0001 (4)	−0.0022 (4)
O1	0.0224 (5)	0.0142 (5)	0.0202 (5)	0.0033 (4)	0.0015 (4)	−0.0020 (4)
C2	0.0164 (6)	0.0151 (6)	0.0142 (6)	0.0012 (5)	0.0016 (5)	−0.0018 (5)
O2	0.0210 (5)	0.0217 (5)	0.0208 (5)	0.0013 (4)	0.0070 (4)	0.0049 (4)
O3	0.0170 (5)	0.0180 (5)	0.0237 (5)	0.0049 (4)	−0.0007 (4)	−0.0018 (4)
C3	0.0208 (7)	0.0155 (6)	0.0243 (7)	−0.0016 (5)	−0.0004 (5)	−0.0058 (5)
C9	0.0184 (6)	0.0176 (6)	0.0212 (7)	−0.0010 (5)	0.0030 (5)	0.0043 (5)
C8	0.0194 (6)	0.0220 (7)	0.0152 (6)	0.0020 (5)	0.0038 (5)	0.0017 (5)
C7	0.0124 (6)	0.0158 (6)	0.0171 (6)	0.0004 (5)	0.0002 (5)	−0.0017 (5)
C6	0.0227 (7)	0.0418 (9)	0.0258 (8)	0.0094 (7)	0.0093 (6)	0.0081 (7)
C5	0.0184 (7)	0.0345 (9)	0.0389 (9)	0.0043 (6)	0.0030 (6)	0.0195 (7)
C4	0.0155 (6)	0.0222 (7)	0.0258 (7)	0.0052 (5)	0.0003 (5)	−0.0036 (6)
C10	0.0147 (6)	0.0158 (6)	0.0227 (7)	−0.0007 (5)	0.0010 (5)	−0.0035 (5)
C11	0.0148 (6)	0.0225 (7)	0.0148 (6)	−0.0027 (5)	0.0021 (5)	−0.0026 (5)
C12	0.0140 (6)	0.0181 (6)	0.0160 (6)	−0.0021 (5)	0.0010 (5)	0.0025 (5)

Geometric parameters (Å, º)

S1—O3	1.4399 (9)	C9—H9	0.9500
S1—O2	1.4419 (10)	C8—C7	1.3920 (18)
S1—C3	1.7570 (13)	C8—H8	0.9500
S1—C2	1.7862 (13)	C7—C12	1.3922 (18)
F1—C10	1.3586 (15)	C6—C4	1.519 (2)
C1—O1	1.2300 (16)	C6—H6A	0.9800
C1—N1	1.3535 (17)	C6—H6B	0.9800
C1—C2	1.5213 (17)	C6—H6C	0.9800
N1—C7	1.4411 (16)	C5—C4	1.519 (2)
N1—C4	1.4876 (16)	C5—H5A	0.9800
C2—H2A	0.9900	C5—H5B	0.9800
C2—H2AB	0.9900	C5—H5C	0.9800
C3—H3A	0.9800	C4—H4	1.0000
C3—H3B	0.9800	C10—C11	1.3732 (19)
C3—H3C	0.9800	C11—C12	1.3892 (19)
C9—C10	1.378 (2)	C11—H11	0.9500
C9—C8	1.3896 (19)	C12—H12	0.9500
O3—S1—O2	117.90 (6)	C8—C7—C12	120.32 (12)
O3—S1—C3	108.18 (6)	C8—C7—N1	120.53 (12)
O2—S1—C3	109.13 (7)	C12—C7—N1	119.13 (12)
O3—S1—C2	106.87 (6)	C4—C6—H6A	109.5
O2—S1—C2	108.27 (6)	C4—C6—H6B	109.5
C3—S1—C2	105.84 (7)	H6A—C6—H6B	109.5
O1—C1—N1	123.48 (12)	C4—C6—H6C	109.5
O1—C1—C2	119.15 (12)	H6A—C6—H6C	109.5
N1—C1—C2	117.29 (11)	H6B—C6—H6C	109.5
C1—N1—C7	121.96 (11)	C4—C5—H5A	109.5
C1—N1—C4	118.22 (11)	C4—C5—H5B	109.5
C7—N1—C4	118.74 (11)	H5A—C5—H5B	109.5
C1—C2—S1	110.27 (9)	C4—C5—H5C	109.5
C1—C2—H2A	109.6	H5A—C5—H5C	109.5
S1—C2—H2A	109.6	H5B—C5—H5C	109.5
C1—C2—H2AB	109.6	N1—C4—C6	111.23 (12)
S1—C2—H2AB	109.6	N1—C4—C5	111.03 (12)
H2A—C2—H2AB	108.1	C6—C4—C5	111.49 (12)
S1—C3—H3A	109.5	N1—C4—H4	107.6
S1—C3—H3B	109.5	C6—C4—H4	107.6
H3A—C3—H3B	109.5	C5—C4—H4	107.6
S1—C3—H3C	109.5	F1—C10—C11	118.07 (12)
H3A—C3—H3C	109.5	F1—C10—C9	118.66 (12)
H3B—C3—H3C	109.5	C11—C10—C9	123.26 (12)
C10—C9—C8	118.19 (12)	C10—C11—C12	118.32 (12)
C10—C9—H9	120.9	C10—C11—H11	120.8
C8—C9—H9	120.9	C12—C11—H11	120.8
C9—C8—C7	119.96 (12)	C11—C12—C7	119.94 (12)
C9—C8—H8	120.0	C11—C12—H12	120.0
C7—C8—H8	120.0	C7—C12—H12	120.0
O1—C1—N1—C7	−168.59 (12)	C1—N1—C7—C12	78.93 (16)
C2—C1—N1—C7	14.68 (17)	C4—N1—C7—C12	−88.93 (15)
O1—C1—N1—C4	−0.67 (19)	C1—N1—C4—C6	139.85 (13)
C2—C1—N1—C4	−177.40 (11)	C7—N1—C4—C6	−51.84 (16)
O1—C1—C2—S1	−69.97 (14)	C1—N1—C4—C5	−95.38 (15)
N1—C1—C2—S1	106.91 (11)	C7—N1—C4—C5	72.93 (16)
O3—S1—C2—C1	−170.32 (9)	C8—C9—C10—F1	−178.38 (11)
O2—S1—C2—C1	−42.36 (11)	C8—C9—C10—C11	0.2 (2)
C3—S1—C2—C1	74.53 (10)	F1—C10—C11—C12	178.69 (11)
C10—C9—C8—C7	−0.3 (2)	C9—C10—C11—C12	0.1 (2)
C9—C8—C7—C12	−0.03 (19)	C10—C11—C12—C7	−0.36 (19)
C9—C8—C7—N1	178.39 (12)	C8—C7—C12—C11	0.34 (19)
C1—N1—C7—C8	−99.51 (15)	N1—C7—C12—C11	−178.10 (11)
C4—N1—C7—C8	92.63 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O3^i	0.99	2.31	3.2025 (16)	150
C3—H3B···O1^ii	0.98	2.55	3.5196 (17)	170
C5—H5A···F1^iii	0.98	2.50	3.4295 (18)	158
C11—H11···O1^iv	0.95	2.39	3.1851 (16)	141
C12—H12···O2^iv	0.95	2.56	3.2955 (16)	134

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y, −z+1; (iii) x, y−1, z; (iv) x, −y+1/2, z+1/2.