Crystal structure and anti­mycobacterial evaluation of 2-(cyclo­hexyl­meth­yl)-7-nitro-5-(tri­fluoro­meth­yl)benzo[d]iso­thia­zol-3(2H)-one

The crystal structure of the title compound features centrosymmetric dimers formed through C—H...O weak hydrogen bonds between a C—H group of the electron-deficient benzene ring and the benzo­thia­zolinone carbonyl O atom with an (10) motif.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.116
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O2       ..N1       .       2.87 Ang.
                                             -x,1/2+y,1/2-z  =      4_455 Check

Author Response: This short O...N contact occurring between the nitro groups of adjacent symmetry-related molecules appears to be a feature of the crystal structure. There are no indications of a possibly missed hydrogen bond.

Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9 Note
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.045 Report

Alert level G
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       5.94 Why ?
PLAT967_ALERT_5_G Note: Two-Theta Cutoff Value in Embedded .res ..       51.0 Degree
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
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

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

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Computing details

2-(Cyclohexylmethyl)-7-nitro-5-(trifluoromethyl)benzo[d]isothiazol-3(2H)-one

Crystal data

C15H15F3N2O3S	F(000) = 1488
Mr = 360.35	Dx = 1.576 Mg m^−3
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 21.9709 (15) Å	Cell parameters from 9947 reflections
b = 5.1271 (4) Å	θ = 2.5–28.4°
c = 27.022 (2) Å	µ = 0.27 mm^−1
β = 93.633 (4)°	T = 100 K
V = 3037.8 (4) Å^3	Needle, yellow
Z = 8	0.20 × 0.06 × 0.06 mm

Data collection

Bruker Kappa Mach3 APEXII diffractometer	2836 independent reflections
Radiation source: microfocus X-ray source	2243 reflections with I > 2σ(I)
Incoatec Helios mirrors monochromator	Rint = 0.100
Detector resolution: 66.67 pixels mm^-1	θmax = 25.5°, θmin = 1.5°
φ and ω scans	h = −26→26
Absorption correction: gaussian (SADABS; Krause et al., 2015)	k = −6→6
Tmin = 0.967, Tmax = 0.992	l = −32→32
61976 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0554P)^2 + 5.9357P] where P = (Fo^2 + 2Fc^2)/3
2836 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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
C3	0.18859 (9)	0.1371 (5)	0.21632 (9)	0.0197 (5)
C3A	0.15790 (10)	0.1247 (5)	0.26275 (8)	0.0183 (5)
C4	0.16991 (10)	−0.0481 (5)	0.30149 (9)	0.0197 (5)
H4	0.201655	−0.173215	0.300101	0.024*
C5	0.13485 (10)	−0.0359 (5)	0.34241 (9)	0.0198 (5)
C6	0.08669 (10)	0.1406 (5)	0.34402 (9)	0.0202 (5)
H6	0.061716	0.142709	0.371460	0.024*
C7	0.07599 (10)	0.3113 (5)	0.30523 (9)	0.0196 (5)
C7A	0.11180 (9)	0.3127 (5)	0.26458 (8)	0.0186 (5)
C8	0.14904 (10)	−0.2056 (5)	0.38629 (9)	0.0217 (5)
C9	0.18439 (10)	0.4007 (5)	0.13941 (8)	0.0207 (5)
H9A	0.227784	0.350627	0.138129	0.025*
H9B	0.181497	0.591480	0.134170	0.025*
C10	0.14732 (10)	0.2631 (5)	0.09739 (8)	0.0209 (5)
H10	0.141760	0.077299	0.107440	0.025*
C11	0.08388 (10)	0.3832 (5)	0.08715 (9)	0.0234 (5)
H11A	0.060785	0.370255	0.117343	0.028*
H11B	0.088125	0.570227	0.078966	0.028*
C12	0.04881 (10)	0.2450 (6)	0.04447 (9)	0.0278 (6)
H12A	0.041006	0.062157	0.053996	0.033*
H12B	0.008923	0.331937	0.037643	0.033*
C13	0.08402 (11)	0.2483 (6)	−0.00212 (9)	0.0283 (6)
H13A	0.088292	0.430440	−0.013581	0.034*
H13B	0.061107	0.149498	−0.028697	0.034*
C14	0.14704 (11)	0.1280 (6)	0.00764 (9)	0.0278 (6)
H14A	0.142728	−0.059395	0.015561	0.033*
H14B	0.169975	0.141924	−0.022619	0.033*
C15	0.18246 (10)	0.2642 (5)	0.05047 (9)	0.0245 (6)
H15A	0.190777	0.446672	0.040981	0.029*
H15B	0.222109	0.175301	0.057240	0.029*
N1	0.02611 (9)	0.4958 (4)	0.30532 (8)	0.0226 (5)
N2	0.16422 (8)	0.3389 (4)	0.18865 (7)	0.0207 (5)
O1	0.22911 (7)	−0.0059 (4)	0.20281 (6)	0.0246 (4)
O2	0.02475 (7)	0.6650 (3)	0.27241 (6)	0.0258 (4)
O3	−0.01168 (8)	0.4766 (4)	0.33673 (7)	0.0300 (4)
F1	0.18323 (6)	−0.4115 (3)	0.37631 (5)	0.0285 (4)
F2	0.17958 (7)	−0.0767 (3)	0.42334 (5)	0.0310 (4)
F3	0.09820 (6)	−0.2979 (3)	0.40528 (5)	0.0289 (4)
S1	0.10703 (2)	0.51050 (12)	0.21373 (2)	0.02003 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C3	0.0068 (10)	0.0277 (13)	0.0242 (13)	−0.0001 (10)	−0.0013 (9)	−0.0037 (10)
C3A	0.0076 (10)	0.0246 (13)	0.0222 (12)	−0.0019 (9)	−0.0016 (9)	−0.0043 (10)
C4	0.0064 (10)	0.0272 (14)	0.0252 (12)	−0.0005 (9)	−0.0017 (9)	−0.0032 (10)
C5	0.0092 (11)	0.0281 (14)	0.0216 (12)	−0.0024 (9)	−0.0023 (9)	−0.0037 (10)
C6	0.0071 (10)	0.0309 (14)	0.0225 (12)	−0.0028 (10)	0.0006 (9)	−0.0050 (10)
C7	0.0069 (10)	0.0263 (13)	0.0254 (12)	−0.0007 (9)	−0.0005 (9)	−0.0052 (10)
C7A	0.0079 (10)	0.0250 (13)	0.0223 (12)	−0.0004 (9)	−0.0043 (9)	−0.0048 (10)
C8	0.0114 (11)	0.0308 (14)	0.0231 (12)	−0.0011 (10)	0.0029 (9)	−0.0044 (11)
C9	0.0098 (11)	0.0313 (14)	0.0211 (12)	−0.0002 (10)	0.0018 (9)	0.0016 (10)
C10	0.0089 (10)	0.0295 (14)	0.0240 (12)	−0.0012 (10)	−0.0011 (9)	0.0017 (10)
C11	0.0081 (11)	0.0362 (14)	0.0258 (13)	0.0000 (10)	0.0005 (9)	0.0032 (11)
C12	0.0101 (11)	0.0443 (17)	0.0287 (13)	−0.0033 (11)	−0.0020 (10)	0.0013 (12)
C13	0.0143 (12)	0.0441 (17)	0.0259 (13)	−0.0040 (11)	−0.0035 (10)	−0.0006 (12)
C14	0.0178 (12)	0.0401 (16)	0.0253 (13)	0.0008 (11)	0.0008 (10)	−0.0029 (12)
C15	0.0112 (11)	0.0374 (15)	0.0249 (13)	0.0014 (10)	0.0009 (9)	−0.0005 (11)
N1	0.0092 (10)	0.0306 (12)	0.0275 (11)	0.0023 (8)	−0.0015 (8)	−0.0055 (10)
N2	0.0100 (9)	0.0278 (11)	0.0243 (11)	0.0004 (8)	0.0002 (8)	0.0002 (9)
O1	0.0121 (8)	0.0344 (10)	0.0277 (9)	0.0061 (7)	0.0051 (7)	0.0018 (8)
O2	0.0152 (8)	0.0298 (10)	0.0319 (10)	0.0052 (7)	−0.0024 (7)	−0.0004 (8)
O3	0.0132 (9)	0.0445 (12)	0.0331 (10)	0.0060 (8)	0.0074 (8)	−0.0038 (9)
F1	0.0221 (7)	0.0346 (9)	0.0291 (8)	0.0088 (6)	0.0047 (6)	0.0042 (7)
F2	0.0263 (8)	0.0426 (9)	0.0229 (7)	−0.0050 (7)	−0.0073 (6)	−0.0018 (7)
F3	0.0131 (7)	0.0415 (9)	0.0326 (8)	−0.0026 (6)	0.0060 (6)	0.0070 (7)
S1	0.0096 (3)	0.0265 (3)	0.0238 (3)	0.0017 (2)	−0.0003 (2)	−0.0008 (3)

Geometric parameters (Å, º)

C3—O1	1.226 (3)	C10—C15	1.526 (3)
C3—N2	1.366 (3)	C10—C11	1.533 (3)
C3—C3A	1.463 (3)	C10—H10	1.0000
C3A—C4	1.384 (3)	C11—C12	1.521 (3)
C3A—C7A	1.402 (3)	C11—H11A	0.9900
C4—C5	1.388 (3)	C11—H11B	0.9900
C4—H4	0.9500	C12—C13	1.519 (3)
C5—C6	1.395 (3)	C12—H12A	0.9900
C5—C8	1.488 (3)	C12—H12B	0.9900
C6—C7	1.374 (3)	C13—C14	1.523 (3)
C6—H6	0.9500	C13—H13A	0.9900
C7—C7A	1.391 (3)	C13—H13B	0.9900
C7—N1	1.448 (3)	C14—C15	1.523 (3)
C7A—S1	1.706 (2)	C14—H14A	0.9900
C8—F1	1.333 (3)	C14—H14B	0.9900
C8—F2	1.343 (3)	C15—H15A	0.9900
C8—F3	1.345 (3)	C15—H15B	0.9900
C9—N2	1.464 (3)	N1—O3	1.228 (3)
C9—C10	1.528 (3)	N1—O2	1.241 (3)
C9—H9A	0.9900	N2—S1	1.709 (2)
C9—H9B	0.9900
O1—C3—N2	123.8 (2)	C11—C10—H10	107.8
O1—C3—C3A	127.7 (2)	C12—C11—C10	111.2 (2)
N2—C3—C3A	108.44 (19)	C12—C11—H11A	109.4
C4—C3A—C7A	121.2 (2)	C10—C11—H11A	109.4
C4—C3A—C3	126.9 (2)	C12—C11—H11B	109.4
C7A—C3A—C3	112.0 (2)	C10—C11—H11B	109.4
C3A—C4—C5	119.0 (2)	H11A—C11—H11B	108.0
C3A—C4—H4	120.5	C13—C12—C11	111.3 (2)
C5—C4—H4	120.5	C13—C12—H12A	109.4
C4—C5—C6	121.0 (2)	C11—C12—H12A	109.4
C4—C5—C8	120.6 (2)	C13—C12—H12B	109.4
C6—C5—C8	118.4 (2)	C11—C12—H12B	109.4
C7—C6—C5	118.9 (2)	H12A—C12—H12B	108.0
C7—C6—H6	120.6	C12—C13—C14	110.9 (2)
C5—C6—H6	120.6	C12—C13—H13A	109.5
C6—C7—C7A	121.8 (2)	C14—C13—H13A	109.5
C6—C7—N1	120.5 (2)	C12—C13—H13B	109.5
C7A—C7—N1	117.6 (2)	C14—C13—H13B	109.5
C7—C7A—C3A	118.1 (2)	H13A—C13—H13B	108.0
C7—C7A—S1	129.07 (18)	C15—C14—C13	111.2 (2)
C3A—C7A—S1	112.84 (18)	C15—C14—H14A	109.4
F1—C8—F2	106.21 (18)	C13—C14—H14A	109.4
F1—C8—F3	106.9 (2)	C15—C14—H14B	109.4
F2—C8—F3	106.07 (18)	C13—C14—H14B	109.4
F1—C8—C5	113.21 (19)	H14A—C14—H14B	108.0
F2—C8—C5	112.1 (2)	C14—C15—C10	111.6 (2)
F3—C8—C5	111.90 (18)	C14—C15—H15A	109.3
N2—C9—C10	113.45 (19)	C10—C15—H15A	109.3
N2—C9—H9A	108.9	C14—C15—H15B	109.3
C10—C9—H9A	108.9	C10—C15—H15B	109.3
N2—C9—H9B	108.9	H15A—C15—H15B	108.0
C10—C9—H9B	108.9	O3—N1—O2	124.3 (2)
H9A—C9—H9B	107.7	O3—N1—C7	119.6 (2)
C15—C10—C9	109.99 (19)	O2—N1—C7	116.06 (19)
C15—C10—C11	110.53 (19)	C3—N2—C9	122.1 (2)
C9—C10—C11	112.6 (2)	C3—N2—S1	116.46 (16)
C15—C10—H10	107.8	C9—N2—S1	121.45 (16)
C9—C10—H10	107.8	C7A—S1—N2	90.24 (10)
O1—C3—C3A—C4	2.0 (4)	C6—C5—C8—F3	41.5 (3)
N2—C3—C3A—C4	−178.5 (2)	N2—C9—C10—C15	−161.7 (2)
O1—C3—C3A—C7A	−177.3 (2)	N2—C9—C10—C11	74.5 (3)
N2—C3—C3A—C7A	2.3 (3)	C15—C10—C11—C12	55.4 (3)
C7A—C3A—C4—C5	0.9 (3)	C9—C10—C11—C12	178.9 (2)
C3—C3A—C4—C5	−178.2 (2)	C10—C11—C12—C13	−56.3 (3)
C3A—C4—C5—C6	2.4 (3)	C11—C12—C13—C14	56.3 (3)
C3A—C4—C5—C8	−175.7 (2)	C12—C13—C14—C15	−55.7 (3)
C4—C5—C6—C7	−2.8 (3)	C13—C14—C15—C10	55.6 (3)
C8—C5—C6—C7	175.3 (2)	C9—C10—C15—C14	179.9 (2)
C5—C6—C7—C7A	0.0 (3)	C11—C10—C15—C14	−55.2 (3)
C5—C6—C7—N1	179.4 (2)	C6—C7—N1—O3	−9.8 (3)
C6—C7—C7A—C3A	3.2 (3)	C7A—C7—N1—O3	169.7 (2)
N1—C7—C7A—C3A	−176.3 (2)	C6—C7—N1—O2	170.6 (2)
C6—C7—C7A—S1	−178.69 (19)	C7A—C7—N1—O2	−9.9 (3)
N1—C7—C7A—S1	1.9 (3)	O1—C3—N2—C9	0.7 (3)
C4—C3A—C7A—C7	−3.6 (3)	C3A—C3—N2—C9	−178.87 (19)
C3—C3A—C7A—C7	175.6 (2)	O1—C3—N2—S1	178.73 (18)
C4—C3A—C7A—S1	177.93 (18)	C3A—C3—N2—S1	−0.8 (2)
C3—C3A—C7A—S1	−2.8 (2)	C10—C9—N2—C3	91.3 (3)
C4—C5—C8—F1	−19.4 (3)	C10—C9—N2—S1	−86.6 (2)
C6—C5—C8—F1	162.4 (2)	C7—C7A—S1—N2	−176.2 (2)
C4—C5—C8—F2	100.7 (3)	C3A—C7A—S1—N2	1.96 (17)
C6—C5—C8—F2	−77.5 (3)	C3—N2—S1—C7A	−0.63 (18)
C4—C5—C8—F3	−140.3 (2)	C9—N2—S1—C7A	177.45 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^i	0.95	2.25	3.193 (3)	175

Symmetry code: (i) −x+1/2, −y−1/2, −z+1/2.