3,5-Bis(tri­fluoro­meth­yl)phenyl 4-methyl­benzene­sulfonate

Mol­ecules of the title compound, C₁₅H₁₀F₆O₃S, are composed of 3,5-bis­(tri­fluoro­meth­yl)phenyl substituted with a toluene-4-sulfonate group. The dihedral angle between two aromatic moieties is 45.10 (5)°. In the crystal, mol­ecules are connected by weak C—H...O and C—H...F contacts. One of the tri­fluoro­methyl groups is disordered.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• Disorder in main residue
• R factor = 0.030
• wR factor = 0.080
• Data-to-parameter ratio = 12.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT910_ALERT_3_C Missing # of FCF Reflection(s) Below Theta(Min)           6 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         38 Report

Alert level G
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...          6 Report
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT177_ALERT_4_G The CIF-Embedded .res File Contains DELU Records          1 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT230_ALERT_2_G Hirshfeld Test Diff for    F6A    --  C15     ..       12.7 s.u.
PLAT242_ALERT_2_G Low    'MainMol' Ueq as Compared to Neighbors of        C15 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F4A     is Constrained at       0.65 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F5A     is Constrained at       0.65 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F6A     is Constrained at       0.65 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F4B     is Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F5B     is Constrained at       0.35 Check
PLAT300_ALERT_4_G Atom Site Occupancy of F6B     is Constrained at       0.35 Check
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1)..         12 % Note
PLAT395_ALERT_2_G Deviating  X-O-Y  Angle from 120 Deg for  O3          117.4 Degree
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         36 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          8 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          8 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities .......     Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Note

   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
  19 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   9 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

3,5-Bis(trifluoromethyl)phenyl 4-methylbenzenesulfonate

Crystal data

C15H10F6O3S	Z = 2
Mr = 384.29	F(000) = 388
Triclinic, P1	Dx = 1.610 Mg m^−3
a = 8.2805 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.6053 (3) Å	Cell parameters from 5437 reflections
c = 12.2396 (4) Å	θ = 3.5–26.0°
α = 103.519 (3)°	µ = 0.28 mm^−1
β = 99.935 (3)°	T = 100 K
γ = 105.188 (3)°	Irregular, colourless
V = 792.56 (5) Å^3	0.4 × 0.25 × 0.24 mm

Data collection

Oxford Diffraction Xcalibur diffractometer	2614 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.013
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	θmax = 26.0°, θmin = 3.5°
ω–scan	h = −10→10
5437 measured reflections	k = −6→10
3070 independent reflections	l = −15→15

Refinement

Refinement on F^2	36 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.080	w = 1/[σ^2(Fo^2) + (0.0445P)^2 + 0.1137P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.002
3070 reflections	Δρmax = 0.27 e Å^−3
254 parameters	Δρmin = −0.37 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.

Refinement. All H atoms were found in a difference map but set to idealized positions and treated as riding with C_Ar—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) and with C_methyl—H = 0.96 Å and U_iso(H) = 1.5U_eq(C).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.18701 (5)	0.27629 (4)	0.03515 (3)	0.01913 (11)
O1	0.07383 (14)	0.23781 (13)	−0.07602 (9)	0.0260 (3)
O2	0.28474 (14)	0.16929 (13)	0.05977 (9)	0.0253 (3)
O3	0.05670 (13)	0.27937 (12)	0.11983 (8)	0.0194 (2)
F1	0.27606 (16)	−0.09183 (13)	0.34224 (9)	0.0447 (3)
F2	0.03104 (14)	−0.12166 (12)	0.38253 (10)	0.0457 (3)
F3	0.26421 (14)	0.01544 (11)	0.51597 (8)	0.0371 (3)
F4A	0.3770 (3)	0.6057 (3)	0.62880 (19)	0.0405 (6)	0.65
F5A	0.1573 (14)	0.6652 (12)	0.5462 (8)	0.0432 (17)	0.65
F6A	0.3974 (7)	0.7323 (6)	0.4990 (3)	0.0254 (6)	0.65
F5B	0.134 (2)	0.669 (2)	0.5219 (14)	0.0266 (17)	0.35
F4B	0.2762 (7)	0.5775 (6)	0.6351 (4)	0.0582 (13)	0.35
F6B	0.3987 (15)	0.7169 (12)	0.5299 (7)	0.055 (2)	0.35
C1	0.32014 (19)	0.48591 (18)	0.07914 (12)	0.0179 (3)
C2	0.48144 (19)	0.53300 (19)	0.15499 (13)	0.0215 (3)
H2	0.5222	0.4533	0.1802	0.026*
C3	0.5807 (2)	0.7017 (2)	0.19247 (13)	0.0246 (3)
H3	0.6894	0.7346	0.2429	0.030*
C4	0.5209 (2)	0.82248 (19)	0.15611 (13)	0.0234 (3)
C5	0.3587 (2)	0.77115 (19)	0.07913 (14)	0.0242 (3)
H5	0.3177	0.8507	0.0538	0.029*
C6	0.2580 (2)	0.60379 (19)	0.03999 (13)	0.0216 (3)
H6	0.1503	0.5704	−0.0117	0.026*
C7	0.6294 (2)	1.0054 (2)	0.19699 (15)	0.0336 (4)
H7A	0.6946	1.0293	0.1418	0.050*
H7B	0.7071	1.0288	0.2710	0.050*
H7C	0.5556	1.0747	0.2042	0.050*
C8	0.12143 (18)	0.28625 (18)	0.23573 (12)	0.0172 (3)
C9	0.12658 (18)	0.13922 (17)	0.26128 (13)	0.0183 (3)
H9	0.0925	0.0376	0.2028	0.022*
C10	0.18379 (19)	0.14705 (18)	0.37620 (13)	0.0183 (3)
C11	0.23417 (19)	0.29824 (18)	0.46388 (13)	0.0193 (3)
H11	0.2714	0.3021	0.5409	0.023*
C12	0.22819 (19)	0.44313 (18)	0.43511 (13)	0.0212 (3)
C13	0.17096 (19)	0.43894 (18)	0.32017 (13)	0.0196 (3)
H13	0.1663	0.5364	0.3010	0.024*
C14	0.1894 (2)	−0.01242 (19)	0.40458 (14)	0.0247 (3)
C15	0.2802 (3)	0.6082 (2)	0.52824 (14)	0.0308 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0247 (2)	0.01547 (19)	0.01623 (19)	0.00521 (15)	0.00510 (15)	0.00420 (14)
O1	0.0326 (6)	0.0220 (6)	0.0168 (5)	0.0023 (5)	0.0022 (5)	0.0034 (4)
O2	0.0344 (6)	0.0198 (5)	0.0274 (6)	0.0126 (5)	0.0131 (5)	0.0088 (5)
O3	0.0201 (5)	0.0210 (5)	0.0170 (5)	0.0058 (4)	0.0030 (4)	0.0070 (4)
F1	0.0808 (9)	0.0347 (6)	0.0450 (7)	0.0411 (6)	0.0343 (6)	0.0212 (5)
F2	0.0434 (6)	0.0265 (5)	0.0610 (8)	−0.0035 (5)	0.0023 (5)	0.0253 (5)
F3	0.0649 (7)	0.0238 (5)	0.0235 (5)	0.0183 (5)	0.0016 (5)	0.0105 (4)
F4A	0.0712 (15)	0.0204 (9)	0.0191 (9)	0.0125 (11)	−0.0070 (11)	0.0012 (7)
F5A	0.038 (3)	0.027 (2)	0.056 (4)	0.0084 (15)	0.022 (3)	−0.008 (2)
F6A	0.0257 (11)	0.0137 (9)	0.0306 (14)	0.0016 (8)	0.0007 (11)	0.0049 (10)
F5B	0.034 (4)	0.011 (2)	0.039 (4)	0.012 (2)	0.017 (3)	0.006 (3)
F4B	0.116 (4)	0.033 (2)	0.0211 (18)	0.039 (3)	−0.005 (3)	−0.0005 (15)
F6B	0.032 (3)	0.037 (4)	0.070 (5)	0.004 (3)	0.009 (4)	−0.023 (3)
C1	0.0217 (7)	0.0169 (7)	0.0149 (7)	0.0049 (6)	0.0063 (6)	0.0042 (6)
C2	0.0247 (8)	0.0249 (8)	0.0169 (7)	0.0095 (7)	0.0054 (6)	0.0077 (6)
C3	0.0227 (8)	0.0302 (8)	0.0152 (7)	0.0036 (7)	0.0027 (6)	0.0027 (6)
C4	0.0279 (8)	0.0203 (8)	0.0187 (8)	0.0031 (7)	0.0113 (6)	0.0007 (6)
C5	0.0280 (8)	0.0200 (8)	0.0286 (9)	0.0102 (7)	0.0108 (7)	0.0092 (7)
C6	0.0213 (8)	0.0217 (8)	0.0221 (8)	0.0070 (6)	0.0043 (6)	0.0076 (6)
C7	0.0381 (10)	0.0219 (8)	0.0314 (10)	0.0005 (7)	0.0106 (8)	−0.0008 (7)
C8	0.0147 (7)	0.0199 (7)	0.0176 (7)	0.0048 (6)	0.0047 (6)	0.0066 (6)
C9	0.0188 (7)	0.0140 (7)	0.0195 (7)	0.0026 (6)	0.0050 (6)	0.0028 (6)
C10	0.0193 (7)	0.0162 (7)	0.0213 (8)	0.0059 (6)	0.0074 (6)	0.0071 (6)
C11	0.0225 (8)	0.0195 (7)	0.0166 (7)	0.0081 (6)	0.0050 (6)	0.0051 (6)
C12	0.0248 (8)	0.0177 (7)	0.0213 (8)	0.0088 (6)	0.0056 (6)	0.0039 (6)
C13	0.0220 (7)	0.0153 (7)	0.0235 (8)	0.0072 (6)	0.0058 (6)	0.0075 (6)
C14	0.0346 (9)	0.0183 (7)	0.0221 (8)	0.0086 (7)	0.0076 (7)	0.0072 (6)
C15	0.0468 (11)	0.0209 (9)	0.0233 (9)	0.0151 (9)	0.0010 (8)	0.0042 (7)

Geometric parameters (Å, º)

S1—O1	1.4234 (11)	C4—C5	1.395 (2)
S1—O2	1.4246 (11)	C4—C7	1.507 (2)
S1—O3	1.6208 (11)	C5—C6	1.382 (2)
S1—C1	1.7488 (15)	C5—H5	0.9300
O3—C8	1.4089 (17)	C6—H6	0.9300
F1—C14	1.3293 (19)	C7—H7A	0.9600
F2—C14	1.3374 (19)	C7—H7B	0.9600
F3—C14	1.3334 (18)	C7—H7C	0.9600
F4A—C15	1.356 (3)	C8—C13	1.378 (2)
F5A—C15	1.270 (11)	C8—C9	1.382 (2)
F6A—C15	1.402 (5)	C9—C10	1.384 (2)
F5B—C15	1.432 (19)	C9—H9	0.9300
F4B—C15	1.398 (5)	C10—C11	1.388 (2)
F6B—C15	1.158 (10)	C10—C14	1.502 (2)
C1—C2	1.387 (2)	C11—C12	1.383 (2)
C1—C6	1.393 (2)	C11—H11	0.9300
C2—C3	1.388 (2)	C12—C13	1.394 (2)
C2—H2	0.9300	C12—C15	1.502 (2)
C3—C4	1.391 (2)	C13—H13	0.9300
C3—H3	0.9300
O1—S1—O2	121.19 (7)	C8—C9—C10	118.28 (13)
O1—S1—O3	102.31 (6)	C8—C9—H9	120.9
O2—S1—O3	108.14 (6)	C10—C9—H9	120.9
O1—S1—C1	110.29 (7)	C9—C10—C11	121.09 (13)
O2—S1—C1	110.36 (7)	C9—C10—C14	118.55 (13)
O3—S1—C1	102.61 (6)	C11—C10—C14	120.37 (13)
C8—O3—S1	117.42 (9)	C12—C11—C10	119.08 (14)
C2—C1—C6	121.31 (14)	C12—C11—H11	120.5
C2—C1—S1	119.98 (12)	C10—C11—H11	120.5
C6—C1—S1	118.66 (11)	C11—C12—C13	121.06 (14)
C1—C2—C3	118.59 (14)	C11—C12—C15	120.26 (14)
C1—C2—H2	120.7	C13—C12—C15	118.67 (13)
C3—C2—H2	120.7	C8—C13—C12	118.07 (13)
C2—C3—C4	121.34 (14)	C8—C13—H13	121.0
C2—C3—H3	119.3	C12—C13—H13	121.0
C4—C3—H3	119.3	F1—C14—F3	107.05 (13)
C3—C4—C5	118.76 (14)	F1—C14—F2	106.36 (13)
C3—C4—C7	121.10 (15)	F3—C14—F2	106.91 (12)
C5—C4—C7	120.14 (15)	F1—C14—C10	111.94 (13)
C6—C5—C4	120.95 (15)	F3—C14—C10	112.39 (13)
C6—C5—H5	119.5	F2—C14—C10	111.81 (13)
C4—C5—H5	119.5	F5A—C15—F4A	111.0 (4)
C5—C6—C1	119.04 (14)	F6B—C15—F4B	114.9 (5)
C5—C6—H6	120.5	F5A—C15—F6A	106.2 (5)
C1—C6—H6	120.5	F4A—C15—F6A	101.2 (2)
C4—C7—H7A	109.5	F6B—C15—F5B	107.7 (8)
C4—C7—H7B	109.5	F4B—C15—F5B	94.9 (7)
H7A—C7—H7B	109.5	F6B—C15—C12	119.4 (5)
C4—C7—H7C	109.5	F5A—C15—C12	115.2 (5)
H7A—C7—H7C	109.5	F4A—C15—C12	112.22 (16)
H7B—C7—H7C	109.5	F4B—C15—C12	109.2 (2)
C13—C8—C9	122.41 (13)	F6A—C15—C12	109.9 (2)
C13—C8—O3	118.51 (12)	F5B—C15—C12	107.7 (7)
C9—C8—O3	119.03 (12)
O1—S1—O3—C8	169.55 (10)	C14—C10—C11—C12	179.80 (14)
O2—S1—O3—C8	40.56 (11)	C10—C11—C12—C13	0.7 (2)
C1—S1—O3—C8	−76.08 (11)	C10—C11—C12—C15	179.37 (15)
O1—S1—C1—C2	−152.88 (12)	C9—C8—C13—C12	0.1 (2)
O2—S1—C1—C2	−16.32 (15)	O3—C8—C13—C12	177.43 (12)
O3—S1—C1—C2	98.72 (13)	C11—C12—C13—C8	−0.4 (2)
O1—S1—C1—C6	29.51 (14)	C15—C12—C13—C8	−179.14 (15)
O2—S1—C1—C6	166.07 (11)	C9—C10—C14—F1	52.61 (19)
O3—S1—C1—C6	−78.89 (12)	C11—C10—C14—F1	−127.77 (16)
C6—C1—C2—C3	0.5 (2)	C9—C10—C14—F3	173.13 (13)
S1—C1—C2—C3	−177.05 (11)	C11—C10—C14—F3	−7.2 (2)
C1—C2—C3—C4	0.4 (2)	C9—C10—C14—F2	−66.61 (18)
C2—C3—C4—C5	−0.9 (2)	C11—C10—C14—F2	113.01 (16)
C2—C3—C4—C7	−179.91 (14)	C11—C12—C15—F6B	116.5 (6)
C3—C4—C5—C6	0.5 (2)	C13—C12—C15—F6B	−64.8 (6)
C7—C4—C5—C6	179.48 (14)	C11—C12—C15—F5A	−109.7 (5)
C4—C5—C6—C1	0.4 (2)	C13—C12—C15—F5A	69.1 (5)
C2—C1—C6—C5	−0.9 (2)	C11—C12—C15—F4A	18.7 (3)
S1—C1—C6—C5	176.65 (12)	C13—C12—C15—F4A	−162.53 (17)
S1—O3—C8—C13	101.10 (13)	C11—C12—C15—F4B	−18.6 (3)
S1—O3—C8—C9	−81.44 (14)	C13—C12—C15—F4B	160.1 (3)
C13—C8—C9—C10	0.0 (2)	C11—C12—C15—F6A	130.5 (3)
O3—C8—C9—C10	−177.35 (12)	C13—C12—C15—F6A	−50.8 (3)
C8—C9—C10—C11	0.3 (2)	C11—C12—C15—F5B	−120.5 (7)
C8—C9—C10—C14	179.88 (13)	C13—C12—C15—F5B	58.2 (7)
C9—C10—C11—C12	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···F4A^i	0.93	2.55	3.308 (3)	139
C9—H9···O1^ii	0.93	2.40	3.2959 (17)	162

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