Crystal structure, PIXEL calculations of inter­molecular inter­action energies and solid-state characterization of the herbicide isoxaflutole

The packing of isoxaflutole mol­ecules can be rationalized in terms of a hierarchy of inter­action energies within columnar and layer arrangements, in each case dominated by the dispersion energy term.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.038
• wR factor = 0.097
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10A     ..O18      .       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H3       ..O21      .       2.71 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          5 Report

Alert level G
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C19 Check
PLAT395_ALERT_2_G Deviating  X-O-Y   Angle From 120 for O1       .      108.9 Degree
PLAT434_ALERT_2_G Short Inter HL..HL Contact F20      ..F20      .       2.83 Ang.
                                                2-x,1-y,1-z  =      3_766 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          7 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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: CrysAlis PRO (Rigaku OD, 2020); cell refinement: CrysAlis PRO (Rigaku OD, 2020); data reduction: CrysAlis PRO (Rigaku OD, 2020); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: XP (Bruker, 1998) and Mercury (Macrae et al., 2020); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF Westrip (2010).

(5-Cyclopropyl-1,2-oxazol-4-yl)[2-(methylsulfonyl)-4-(trifluoromethyl)\ phenyl]methanone

Crystal data

C15H12F3NO4S	F(000) = 736
Mr = 359.32	Dx = 1.604 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.5689 (16) Å	Cell parameters from 2902 reflections
b = 9.2906 (8) Å	θ = 5.0–29.8°
c = 13.4358 (15) Å	µ = 0.27 mm^−1
β = 118.530 (15)°	T = 193 K
V = 1488.1 (3) Å^3	Prism, colourless
Z = 4	0.25 × 0.10 × 0.08 mm

Data collection

Xcalibur, Ruby, Gemini ultra diffractometer	3275 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source	2667 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 10.3575 pixels mm^-1	θmax = 27.1°, θmin = 2.8°
ω scans	h = −17→16
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2020)	k = −11→9
Tmin = 0.925, Tmax = 1.000	l = −17→17
9962 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.038	Only H-atom displacement parameters refined
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.6729P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max = 0.001
3275 reflections	Δρmax = 0.31 e Å^−3
231 parameters	Δρmin = −0.35 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0203 (15)

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.

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

	x	y	z	Uiso*/Ueq
O1	0.24820 (10)	0.73141 (14)	0.02968 (10)	0.0294 (3)
N2	0.32693 (13)	0.75772 (18)	−0.01032 (12)	0.0306 (4)
C3	0.42144 (15)	0.7107 (2)	0.06926 (14)	0.0258 (4)
H3	0.4898	0.7158	0.0662	0.033 (5)*
C4	0.41253 (14)	0.65039 (18)	0.16220 (13)	0.0217 (4)
C5	0.30138 (14)	0.66771 (19)	0.13150 (13)	0.0225 (4)
C6	0.49824 (14)	0.58226 (19)	0.26500 (14)	0.0242 (4)
O7	0.47773 (11)	0.52442 (17)	0.33418 (11)	0.0398 (4)
C8	0.23389 (15)	0.6311 (2)	0.18562 (15)	0.0283 (4)
H8	0.2763	0.6121	0.2689	0.051 (6)*
C9	0.11929 (16)	0.6956 (2)	0.14281 (18)	0.0364 (5)
H9A	0.0941	0.7183	0.1991	0.047 (6)*
H9B	0.0930	0.7637	0.0785	0.061 (8)*
C10	0.12928 (17)	0.5426 (2)	0.11990 (19)	0.0381 (5)
H10A	0.1094	0.5152	0.0413	0.050 (7)*
H10B	0.1105	0.4698	0.1620	0.059 (7)*
C11	0.61644 (14)	0.58208 (18)	0.28108 (13)	0.0216 (4)
C12	0.70654 (13)	0.65149 (18)	0.37110 (13)	0.0193 (3)
C13	0.81286 (13)	0.64965 (18)	0.38042 (13)	0.0203 (3)
H13	0.8729	0.6992	0.4408	0.024 (5)*
C14	0.83109 (14)	0.57524 (18)	0.30129 (13)	0.0206 (3)
C15	0.74423 (14)	0.50231 (18)	0.21388 (14)	0.0234 (4)
H15	0.7574	0.4491	0.1610	0.035 (5)*
C16	0.63762 (14)	0.50723 (19)	0.20371 (14)	0.0255 (4)
H16	0.5778	0.4584	0.1426	0.031 (5)*
S17	0.69237 (4)	0.74778 (5)	0.47805 (3)	0.02312 (14)
O18	0.78878 (12)	0.83833 (16)	0.53321 (11)	0.0387 (4)
C19	0.94598 (15)	0.5802 (2)	0.31081 (14)	0.0258 (4)
F20	1.02531 (9)	0.53642 (16)	0.41237 (10)	0.0490 (4)
O21	0.58332 (12)	0.81258 (15)	0.42868 (11)	0.0375 (4)
C22	0.69982 (18)	0.6145 (2)	0.57370 (15)	0.0336 (4)
H22A	0.7714	0.5632	0.6026	0.048 (7)*
H22B	0.6378	0.5465	0.5351	0.057 (7)*
H22C	0.6945	0.6594	0.6370	0.046 (6)*
F23	0.95559 (9)	0.49764 (13)	0.23536 (10)	0.0394 (3)
F24	0.97390 (10)	0.71318 (13)	0.29720 (12)	0.0467 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0211 (7)	0.0400 (8)	0.0249 (6)	0.0034 (5)	0.0093 (5)	0.0067 (5)
N2	0.0295 (9)	0.0387 (10)	0.0257 (7)	−0.0010 (7)	0.0150 (7)	0.0041 (6)
C3	0.0232 (9)	0.0302 (10)	0.0261 (8)	−0.0031 (7)	0.0133 (7)	0.0004 (7)
C4	0.0185 (8)	0.0246 (9)	0.0229 (8)	−0.0039 (7)	0.0106 (7)	−0.0007 (7)
C5	0.0198 (8)	0.0243 (9)	0.0214 (8)	−0.0009 (7)	0.0081 (7)	0.0002 (7)
C6	0.0188 (8)	0.0295 (10)	0.0249 (8)	−0.0023 (7)	0.0110 (7)	0.0016 (7)
O7	0.0245 (7)	0.0600 (10)	0.0369 (7)	0.0013 (7)	0.0162 (6)	0.0207 (7)
C8	0.0191 (9)	0.0374 (11)	0.0299 (9)	−0.0001 (8)	0.0129 (7)	0.0032 (8)
C9	0.0270 (10)	0.0378 (11)	0.0528 (12)	0.0047 (9)	0.0259 (9)	0.0006 (9)
C10	0.0296 (11)	0.0376 (11)	0.0547 (12)	−0.0076 (9)	0.0263 (10)	−0.0072 (9)
C11	0.0176 (8)	0.0243 (9)	0.0230 (8)	0.0003 (7)	0.0099 (7)	0.0054 (6)
C12	0.0181 (8)	0.0202 (8)	0.0207 (7)	0.0016 (6)	0.0100 (6)	0.0020 (6)
C13	0.0171 (8)	0.0213 (8)	0.0207 (8)	−0.0003 (6)	0.0076 (6)	0.0004 (6)
C14	0.0193 (8)	0.0210 (8)	0.0235 (8)	0.0024 (6)	0.0118 (7)	0.0042 (6)
C15	0.0263 (9)	0.0231 (9)	0.0235 (8)	0.0000 (7)	0.0140 (7)	−0.0008 (7)
C16	0.0227 (9)	0.0281 (10)	0.0240 (8)	−0.0061 (7)	0.0097 (7)	−0.0044 (7)
S17	0.0255 (3)	0.0244 (2)	0.0244 (2)	0.00307 (17)	0.01593 (19)	0.00053 (16)
O18	0.0450 (9)	0.0421 (8)	0.0388 (7)	−0.0153 (7)	0.0280 (7)	−0.0174 (6)
C19	0.0238 (9)	0.0284 (10)	0.0296 (9)	0.0024 (7)	0.0164 (7)	0.0029 (7)
F20	0.0193 (6)	0.0889 (10)	0.0363 (6)	0.0101 (6)	0.0112 (5)	0.0143 (6)
O21	0.0378 (8)	0.0411 (8)	0.0414 (8)	0.0201 (6)	0.0252 (7)	0.0109 (6)
C22	0.0411 (12)	0.0370 (11)	0.0263 (9)	0.0069 (9)	0.0191 (9)	0.0082 (8)
F23	0.0358 (7)	0.0455 (7)	0.0497 (7)	0.0046 (5)	0.0306 (6)	−0.0083 (5)
F24	0.0436 (7)	0.0327 (7)	0.0844 (9)	−0.0068 (6)	0.0471 (7)	0.0000 (6)

Geometric parameters (Å, º)

O1—C5	1.341 (2)	C11—C12	1.400 (2)
O1—N2	1.4276 (19)	C12—C13	1.387 (2)
N2—C3	1.292 (2)	C12—S17	1.7794 (16)
C3—C4	1.426 (2)	C13—C14	1.386 (2)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.370 (2)	C14—C15	1.380 (2)
C4—C6	1.458 (2)	C14—C19	1.503 (2)
C5—C8	1.456 (2)	C15—C16	1.387 (2)
C6—O7	1.215 (2)	C15—H15	0.9500
C6—C11	1.513 (2)	C16—H16	0.9500
C8—C9	1.501 (3)	S17—O18	1.4291 (14)
C8—C10	1.508 (3)	S17—O21	1.4333 (14)
C8—H8	1.0000	S17—C22	1.7521 (18)
C9—C10	1.474 (3)	C19—F23	1.326 (2)
C9—H9A	0.9900	C19—F24	1.330 (2)
C9—H9B	0.9900	C19—F20	1.335 (2)
C10—H10A	0.9900	C22—H22A	0.9800
C10—H10B	0.9900	C22—H22B	0.9800
C11—C16	1.390 (2)	C22—H22C	0.9800
C5—O1—N2	108.95 (12)	C12—C11—C6	123.48 (15)
C3—N2—O1	104.84 (13)	C13—C12—C11	120.91 (14)
N2—C3—C4	113.07 (16)	C13—C12—S17	116.24 (12)
N2—C3—H3	123.5	C11—C12—S17	122.85 (12)
C4—C3—H3	123.5	C14—C13—C12	119.72 (15)
C5—C4—C3	103.41 (14)	C14—C13—H13	120.1
C5—C4—C6	126.98 (15)	C12—C13—H13	120.1
C3—C4—C6	129.59 (15)	C15—C14—C13	120.32 (15)
O1—C5—C4	109.72 (14)	C15—C14—C19	121.13 (15)
O1—C5—C8	116.89 (15)	C13—C14—C19	118.51 (15)
C4—C5—C8	133.39 (15)	C14—C15—C16	119.61 (15)
O7—C6—C4	123.08 (16)	C14—C15—H15	120.2
O7—C6—C11	120.32 (15)	C16—C15—H15	120.2
C4—C6—C11	116.57 (13)	C15—C16—C11	121.41 (15)
C5—C8—C9	119.94 (16)	C15—C16—H16	119.3
C5—C8—C10	118.40 (16)	C11—C16—H16	119.3
C9—C8—C10	58.67 (13)	O18—S17—O21	118.66 (9)
C5—C8—H8	115.9	O18—S17—C22	108.52 (10)
C9—C8—H8	115.9	O21—S17—C22	108.75 (9)
C10—C8—H8	115.9	O18—S17—C12	106.83 (8)
C10—C9—C8	60.89 (13)	O21—S17—C12	108.86 (8)
C10—C9—H9A	117.7	C22—S17—C12	104.27 (9)
C8—C9—H9A	117.7	F23—C19—F24	107.07 (14)
C10—C9—H9B	117.7	F23—C19—F20	106.22 (14)
C8—C9—H9B	117.7	F24—C19—F20	106.25 (16)
H9A—C9—H9B	114.8	F23—C19—C14	113.20 (15)
C9—C10—C8	60.44 (13)	F24—C19—C14	111.64 (14)
C9—C10—H10A	117.7	F20—C19—C14	112.02 (13)
C8—C10—H10A	117.7	S17—C22—H22A	109.5
C9—C10—H10B	117.7	S17—C22—H22B	109.5
C8—C10—H10B	117.7	H22A—C22—H22B	109.5
H10A—C10—H10B	114.8	S17—C22—H22C	109.5
C16—C11—C12	117.98 (15)	H22A—C22—H22C	109.5
C16—C11—C6	118.53 (15)	H22B—C22—H22C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O21^i	0.95	2.35	3.214 (2)	151
C10—H10A···O18^i	0.99	2.63	3.355 (2)	130
C3—H3···O21^ii	0.95	2.71	3.522 (2)	144

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2.