4-Methyl­phen­yl benz­yl sulfone

In the title compound, C₁₄H₁₄O₂S, the dihedral angle between the two benzene rings is 15.5 (1)°. In the crystal structure, an inter­molecular C—H...O inter­action links the mol­ecules into zigzag chains along the a axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.086
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.23
           From the CIF: _reflns_number_total               2225
           Count of symmetry unique reflns         1322
           Completeness (_total/calc)            168.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       903
           Fraction of Friedel pairs measured     0.683
           Are heavy atom types Z>Si present        yes

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

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

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXL97.

4-Methylphenyl benzyl sulfone

Crystal data

C14H14O2S	F(000) = 520
Mr = 246.31	Dx = 1.323 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3217 reflections
a = 5.7135 (5) Å	θ = 2.4–25.0°
b = 12.6191 (10) Å	µ = 0.25 mm^−1
c = 17.1549 (14) Å	T = 298 K
V = 1236.85 (18) Å^3	Block, colorless
Z = 4	0.26 × 0.24 × 0.16 mm

Data collection

Bruker SMART APEX area-detector diffractometer	2225 independent reflections
Radiation source: fine-focus sealed tube	2140 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
φ and ω scans	θmax = 25.2°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→4
Tmin = 0.938, Tmax = 0.953	k = −14→15
6597 measured reflections	l = −20→20

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)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 0.2051P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.016
2225 reflections	Δρmax = 0.21 e Å^−3
155 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Absolute structure: Flack (1983), 903 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.08 (8)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
S1	0.13500 (9)	0.41645 (4)	0.09205 (3)	0.03990 (16)
O1	0.1942 (3)	0.45241 (13)	0.16830 (8)	0.0596 (5)
O2	−0.1037 (3)	0.38741 (13)	0.07654 (10)	0.0589 (4)
C1	0.4770 (6)	0.7298 (2)	−0.14859 (18)	0.0797 (9)
H1A	0.4070	0.7139	−0.1981	0.120*
H1B	0.6438	0.7218	−0.1523	0.120*
H1C	0.4402	0.8014	−0.1342	0.120*
C2	0.3835 (4)	0.65519 (16)	−0.08789 (13)	0.0495 (5)
C3	0.1799 (4)	0.59898 (18)	−0.09930 (14)	0.0548 (6)
H3	0.0952	0.6095	−0.1449	0.066*
C4	0.0979 (4)	0.52747 (17)	−0.04489 (14)	0.0492 (6)
H4	−0.0390	0.4896	−0.0541	0.059*
C5	0.2223 (4)	0.51299 (16)	0.02354 (12)	0.0386 (5)
C6	0.4268 (4)	0.56914 (18)	0.03654 (13)	0.0482 (5)
H6	0.5112	0.5591	0.0823	0.058*
C7	0.5042 (4)	0.63986 (19)	−0.01867 (14)	0.0514 (6)
H7	0.6403	0.6782	−0.0094	0.062*
C8	0.3203 (4)	0.30688 (16)	0.06840 (12)	0.0401 (5)
H8A	0.2706	0.2770	0.0190	0.048*
H8B	0.4795	0.3322	0.0621	0.048*
C9	0.3170 (4)	0.22157 (16)	0.12934 (11)	0.0372 (5)
C10	0.1324 (4)	0.15123 (17)	0.13581 (11)	0.0431 (5)
H10	0.0045	0.1574	0.1026	0.052*
C11	0.1366 (4)	0.07162 (17)	0.19149 (12)	0.0475 (5)
H11	0.0108	0.0252	0.1960	0.057*
C12	0.3262 (5)	0.06126 (18)	0.23996 (12)	0.0503 (6)
H12	0.3301	0.0071	0.2767	0.060*
C13	0.5108 (5)	0.1310 (2)	0.23426 (14)	0.0544 (6)
H13	0.6397	0.1237	0.2669	0.065*
C14	0.5043 (4)	0.21169 (18)	0.17992 (14)	0.0468 (5)
H14	0.6272	0.2599	0.1773	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0357 (3)	0.0400 (3)	0.0440 (3)	−0.0010 (2)	0.0070 (2)	−0.0035 (2)
O1	0.0770 (13)	0.0566 (9)	0.0452 (8)	−0.0027 (9)	0.0126 (8)	−0.0115 (7)
O2	0.0341 (8)	0.0599 (9)	0.0829 (12)	−0.0037 (7)	0.0069 (8)	0.0113 (8)
C1	0.091 (2)	0.0661 (18)	0.082 (2)	−0.0108 (17)	−0.0061 (18)	0.0290 (16)
C2	0.0551 (14)	0.0382 (10)	0.0553 (13)	0.0051 (11)	0.0034 (13)	0.0028 (10)
C3	0.0585 (14)	0.0510 (13)	0.0550 (12)	0.0024 (11)	−0.0145 (12)	0.0055 (11)
C4	0.0422 (12)	0.0433 (12)	0.0622 (14)	−0.0060 (10)	−0.0119 (11)	−0.0019 (11)
C5	0.0360 (11)	0.0361 (10)	0.0438 (11)	0.0004 (8)	0.0020 (9)	−0.0045 (9)
C6	0.0453 (13)	0.0515 (13)	0.0477 (11)	−0.0069 (11)	−0.0095 (10)	−0.0014 (11)
C7	0.0444 (13)	0.0463 (13)	0.0634 (14)	−0.0132 (10)	−0.0019 (11)	0.0016 (11)
C8	0.0382 (11)	0.0432 (11)	0.0389 (10)	0.0020 (9)	0.0087 (9)	−0.0013 (8)
C9	0.0333 (11)	0.0391 (10)	0.0392 (10)	0.0018 (9)	0.0062 (9)	−0.0042 (8)
C10	0.0394 (11)	0.0497 (12)	0.0403 (10)	−0.0024 (11)	−0.0026 (10)	−0.0032 (9)
C11	0.0483 (13)	0.0459 (11)	0.0481 (11)	−0.0087 (12)	0.0043 (11)	−0.0018 (10)
C12	0.0616 (15)	0.0452 (12)	0.0442 (11)	0.0015 (12)	0.0010 (11)	0.0044 (10)
C13	0.0468 (13)	0.0624 (15)	0.0540 (13)	0.0031 (12)	−0.0096 (12)	0.0067 (12)
C14	0.0342 (12)	0.0492 (12)	0.0571 (13)	−0.0043 (10)	−0.0022 (10)	0.0027 (11)

Geometric parameters (Å, º)

S1—O1	1.4252 (16)	C6—H6	0.9300
S1—O2	1.4370 (17)	C7—H7	0.9300
S1—C5	1.765 (2)	C8—C9	1.501 (3)
S1—C8	1.788 (2)	C8—H8A	0.9700
C1—C2	1.502 (3)	C8—H8B	0.9700
C1—H1A	0.9600	C9—C10	1.383 (3)
C1—H1B	0.9600	C9—C14	1.383 (3)
C1—H1C	0.9600	C10—C11	1.386 (3)
C2—C3	1.376 (3)	C10—H10	0.9300
C2—C7	1.387 (3)	C11—C12	1.372 (3)
C3—C4	1.380 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.377 (4)
C4—C5	1.385 (3)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.381 (3)
C5—C6	1.384 (3)	C13—H13	0.9300
C6—C7	1.374 (3)	C14—H14	0.9300
O1—S1—O2	118.45 (11)	C6—C7—C2	121.4 (2)
O1—S1—C5	108.93 (10)	C6—C7—H7	119.3
O2—S1—C5	108.73 (10)	C2—C7—H7	119.3
O1—S1—C8	108.29 (10)	C9—C8—S1	112.91 (14)
O2—S1—C8	108.83 (11)	C9—C8—H8A	109.0
C5—S1—C8	102.43 (9)	S1—C8—H8A	109.0
C2—C1—H1A	109.5	C9—C8—H8B	109.0
C2—C1—H1B	109.5	S1—C8—H8B	109.0
H1A—C1—H1B	109.5	H8A—C8—H8B	107.8
C2—C1—H1C	109.5	C10—C9—C14	118.81 (19)
H1A—C1—H1C	109.5	C10—C9—C8	121.72 (19)
H1B—C1—H1C	109.5	C14—C9—C8	119.47 (19)
C3—C2—C7	118.0 (2)	C9—C10—C11	120.5 (2)
C3—C2—C1	121.7 (2)	C9—C10—H10	119.8
C7—C2—C1	120.3 (2)	C11—C10—H10	119.8
C2—C3—C4	121.8 (2)	C12—C11—C10	120.0 (2)
C2—C3—H3	119.1	C12—C11—H11	120.0
C4—C3—H3	119.1	C10—C11—H11	120.0
C3—C4—C5	119.0 (2)	C11—C12—C13	120.1 (2)
C3—C4—H4	120.5	C11—C12—H12	120.0
C5—C4—H4	120.5	C13—C12—H12	120.0
C6—C5—C4	120.2 (2)	C12—C13—C14	119.9 (2)
C6—C5—S1	118.99 (17)	C12—C13—H13	120.0
C4—C5—S1	120.70 (16)	C14—C13—H13	120.0
C7—C6—C5	119.5 (2)	C13—C14—C9	120.7 (2)
C7—C6—H6	120.2	C13—C14—H14	119.7
C5—C6—H6	120.2	C9—C14—H14	119.7
C7—C2—C3—C4	−1.3 (3)	C1—C2—C7—C6	−177.6 (2)
C1—C2—C3—C4	177.6 (2)	O1—S1—C8—C9	52.69 (18)
C2—C3—C4—C5	0.9 (3)	O2—S1—C8—C9	−77.32 (17)
C3—C4—C5—C6	−0.5 (3)	C5—S1—C8—C9	167.69 (15)
C3—C4—C5—S1	−175.92 (18)	S1—C8—C9—C10	76.8 (2)
O1—S1—C5—C6	36.1 (2)	S1—C8—C9—C14	−104.0 (2)
O2—S1—C5—C6	166.53 (17)	C14—C9—C10—C11	−0.7 (3)
C8—S1—C5—C6	−78.41 (18)	C8—C9—C10—C11	178.47 (19)
O1—S1—C5—C4	−148.35 (18)	C9—C10—C11—C12	−0.9 (3)
O2—S1—C5—C4	−18.0 (2)	C10—C11—C12—C13	1.1 (3)
C8—S1—C5—C4	97.11 (19)	C11—C12—C13—C14	0.3 (4)
C4—C5—C6—C7	0.5 (3)	C12—C13—C14—C9	−1.9 (4)
S1—C5—C6—C7	176.03 (19)	C10—C9—C14—C13	2.1 (3)
C5—C6—C7—C2	−0.9 (3)	C8—C9—C14—C13	−177.1 (2)
C3—C2—C7—C6	1.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O2^i	0.97	2.49	3.447 (3)	168

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