2-(Benzene­sulfonyl)-1-(4-bromo­phenyl)­ethyne

The title compound, C₁₄H₉BrO₂S, contains benzene­sulfonyl and 4-bromo­phenyl moieties linked by an acetyl­ene fragment. The crystal packing is stabilized by weak van der Waals interactions and intermolecular π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.030
• wR factor = 0.069
• Data-to-parameter ratio = 9.3

checkCIF/PLATON results

No syntax errors found



Alert level C
REFNR01_ALERT_3_C  Ratio of reflections to parameters is < 10 for a
            centrosymmetric structure
            sine(theta)/lambda                0.6493
            Proportion of unique data used    0.5028
            Ratio reflections to parameters   9.2577
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.26
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C2     -   C3     ...       1.43 Ang.

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

   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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: PROCESS-AUTO; cell refinement: PROCESS-AUTO; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97; program(s) used to refine structure: CRYSTALS; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure 3.6.0.

(I)

Crystal data

C14H9BrO2S	F(000) = 640.00
Mr = 321.19	Dx = 1.626 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2yn	Cell parameters from 7173 reflections
a = 5.8032 (3) Å	θ = 1.9–27.4°
b = 21.161 (1) Å	µ = 3.29 mm^−1
c = 10.6863 (5) Å	T = 293 K
β = 90.748 (1)°	Chunk, yellow
V = 1312.2 (1) Å^3	0.53 × 0.49 × 0.33 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer	1509 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.055
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −6→7
Tmin = 0.194, Tmax = 0.338	k = −27→27
12268 measured reflections	l = −13→13
3001 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0005Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.030	(Δ/σ)max < 0.001
wR(F^2) = 0.069	Δρmax = 0.28 e Å^−3
S = 1.03	Δρmin = −0.35 e Å^−3
1509 reflections	Extinction correction: Larson (1970) Crystallographic Computing eq. 22
163 parameters	Extinction coefficient: 73 (9)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using reflections with F² > 3.0 σ(F²). The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Br1	1.26523 (7)	0.65012 (2)	1.01950 (4)	0.0767 (2)
S1	0.4135 (1)	0.38607 (4)	0.55121 (8)	0.0471 (3)
O1	0.1775 (4)	0.4051 (1)	0.5493 (2)	0.0649 (8)
O2	0.5236 (5)	0.3720 (1)	0.4358 (2)	0.0686 (9)
C1	0.5704 (6)	0.4432 (2)	0.6262 (3)	0.053 (1)
C2	0.6886 (6)	0.4768 (2)	0.6886 (3)	0.051 (1)
C3	0.8276 (6)	0.5176 (1)	0.7656 (3)	0.045 (1)
C4	1.0388 (6)	0.5393 (1)	0.7251 (3)	0.047 (1)
C5	1.1695 (6)	0.5788 (2)	0.8005 (3)	0.049 (1)
C6	1.0867 (6)	0.5957 (1)	0.9167 (3)	0.048 (1)
C7	0.8781 (6)	0.5747 (2)	0.9587 (3)	0.059 (1)
C8	0.7483 (6)	0.5355 (2)	0.8827 (3)	0.056 (1)
C9	0.4459 (6)	0.3213 (1)	0.6528 (3)	0.044 (1)
C10	0.6420 (6)	0.2851 (2)	0.6491 (3)	0.057 (1)
C11	0.6599 (8)	0.2338 (2)	0.7315 (4)	0.069 (1)
C12	0.4864 (9)	0.2212 (2)	0.8138 (4)	0.076 (1)
C13	0.2912 (8)	0.2577 (2)	0.8153 (4)	0.075 (2)
C14	0.2706 (7)	0.3081 (2)	0.7356 (3)	0.057 (1)
H1	1.0951	0.5261	0.6431	0.057*
H2	1.3188	0.5947	0.7725	0.059*
H3	0.8234	0.5870	1.0416	0.070*
H4	0.5987	0.5198	0.9108	0.067*
H5	0.7652	0.2950	0.5904	0.068*
H6	0.7980	0.2071	0.7309	0.082*
H7	0.5018	0.1852	0.8710	0.091*
H8	0.1676	0.2477	0.8737	0.090*
H9	0.1330	0.3350	0.7375	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0794 (3)	0.0766 (3)	0.0737 (3)	−0.0050 (2)	−0.0224 (2)	−0.0252 (2)
S1	0.0563 (6)	0.0449 (5)	0.0400 (5)	−0.0058 (4)	−0.0032 (4)	−0.0024 (4)
O1	0.057 (2)	0.061 (2)	0.076 (2)	0.002 (1)	−0.017 (1)	0.002 (1)
O2	0.099 (2)	0.068 (2)	0.040 (1)	−0.007 (2)	0.013 (1)	−0.002 (1)
C1	0.063 (2)	0.044 (2)	0.053 (2)	−0.004 (2)	−0.006 (2)	−0.000 (2)
C2	0.059 (2)	0.041 (2)	0.053 (2)	−0.000 (2)	−0.005 (2)	0.004 (2)
C3	0.053 (2)	0.037 (2)	0.044 (2)	−0.001 (2)	−0.010 (2)	0.002 (2)
C4	0.053 (2)	0.049 (2)	0.041 (2)	0.001 (2)	0.002 (2)	−0.003 (2)
C5	0.045 (2)	0.050 (2)	0.051 (2)	−0.004 (2)	−0.002 (2)	0.002 (2)
C6	0.049 (2)	0.045 (2)	0.048 (2)	0.001 (2)	−0.016 (2)	−0.006 (2)
C7	0.057 (2)	0.074 (3)	0.045 (2)	0.006 (2)	−0.001 (2)	−0.010 (2)
C8	0.050 (2)	0.064 (2)	0.053 (2)	−0.005 (2)	0.002 (2)	0.004 (2)
C9	0.052 (2)	0.040 (2)	0.040 (2)	−0.007 (2)	−0.002 (2)	−0.004 (1)
C10	0.059 (2)	0.059 (2)	0.052 (2)	0.001 (2)	−0.006 (2)	−0.010 (2)
C11	0.081 (3)	0.053 (3)	0.073 (3)	0.014 (2)	−0.032 (2)	−0.012 (2)
C12	0.109 (4)	0.053 (3)	0.065 (3)	−0.023 (3)	−0.032 (3)	0.011 (2)
C13	0.078 (3)	0.081 (3)	0.065 (3)	−0.025 (3)	−0.008 (2)	0.016 (2)
C14	0.058 (2)	0.063 (2)	0.051 (2)	−0.007 (2)	0.001 (2)	0.005 (2)

Geometric parameters (Å, º)

Br1—C6	1.892 (3)	C9—C14	1.385 (5)
S1—O1	1.427 (3)	C10—C11	1.400 (5)
S1—O2	1.428 (3)	C11—C12	1.372 (6)
S1—C1	1.708 (3)	C12—C13	1.372 (7)
S1—C9	1.756 (3)	C13—C14	1.369 (6)
C1—C2	1.187 (5)	C4—H1	0.9800
C2—C3	1.433 (5)	C5—H2	0.9800
C3—C4	1.384 (5)	C7—H3	0.9800
C3—C8	1.391 (5)	C8—H4	0.9800
C4—C5	1.382 (5)	C10—H5	0.9800
C5—C6	1.384 (5)	C11—H6	0.9800
C6—C7	1.370 (5)	C12—H7	0.9800
C7—C8	1.379 (5)	C13—H8	0.9800
C9—C10	1.374 (5)	C14—H9	0.9800
Br1—C6—C5	119.0 (2)	C9—C14—C13	119.7 (4)
Br1—C6—C7	119.1 (3)	C10—C11—C12	120.3 (4)
O2—S1—O1	119.1 (2)	C11—C12—C13	120.7 (4)
C1—S1—O1	108.2 (2)	C12—C13—C14	119.8 (4)
C9—S1—O1	108.9 (2)	C3—C4—H1	119.5015
C1—S1—O2	108.1 (2)	C3—C8—H4	119.2721
C9—S1—O2	109.0 (2)	C4—C5—H2	120.6741
S1—C1—C2	171.4 (3)	H1—C4—C5	120.5012
C9—S1—C1	102.1 (2)	H2—C5—C6	120.3002
S1—C9—C10	120.0 (3)	C6—C7—H3	120.5812
S1—C9—C14	118.6 (3)	H3—C7—C8	120.7318
C1—C2—C3	178.8 (4)	C7—C8—H4	120.1318
C2—C3—C4	120.9 (3)	C9—C10—H5	120.6913
C2—C3—C8	119.3 (3)	C9—C14—H9	120.1135
C3—C4—C5	120.0 (3)	H5—C10—C11	121.2953
C8—C3—C4	119.7 (3)	C10—C11—H6	119.7503
C3—C8—C7	120.6 (3)	H6—C11—C12	119.9112
C4—C5—C6	119.0 (3)	C11—C12—H7	119.3194
C5—C6—C7	122.0 (3)	C12—C13—H8	119.7574
C6—C7—C8	118.7 (3)	H7—C12—C13	119.9784
C14—C9—C10	121.4 (3)	C13—C14—H9	120.1805
C9—C10—C11	118.0 (3)	H8—C13—C14	120.4120
O1—S1—C9—C10	164.7 (3)	C4—C5—C6—C7	−0.5 (5)
O1—S1—C9—C14	−15.3 (3)	Br1—C6—C7—C8	179.5 (3)
O2—S1—C9—C10	33.2 (3)	C5—C6—C7—C8	0.3 (5)
O2—S1—C9—C14	−146.8 (3)	C6—C7—C8—C3	−0.1 (4)
C1—S1—C9—C10	−81.0 (3)	S1—C9—C10—C11	−179.8 (3)
C1—S1—C9—C14	99.0 (3)	C14—C9—C10—C11	0.3 (5)
C2—C3—C4—C5	179.7 (3)	S1—C9—C14—C13	179.7 (3)
C8—C3—C4—C5	−0.3 (5)	C10—C9—C14—C13	−0.4 (5)
C2—C3—C8—C7	−179.9 (3)	C9—C10—C11—C12	−0.6 (6)
C4—C3—C8—C7	0.1 (4)	C10—C11—C12—C13	1.1 (7)
C3—C4—C5—C6	0.5 (5)	C11—C12—C13—C14	−1.2 (7)
C4—C5—C6—Br1	−179.7 (3)	C12—C13—C14—C9	0.8 (6)