Crystal structure of phenyl 2,4,5-tri­chloro­benzene­sulfonate

Riley, S.; Staples, R.J.; Biros, S.M.; Ngassa, F.N.

doi:10.1107/S2056989016007325

research communications

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Volume 72| Part 6| June 2016| Pages 789-792

https://doi.org/10.1107/S2056989016007325

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Crystal structure of phenyl 2,4,5-trichlorobenzenesulfonate

Sean Riley,^a Richard J. Staples,^b Shannon M. Biros ^a and Felix N. Ngassa ^a ^*

^aDepartment of Chemistry, Grand Valley State University, 1 Campus Dr., Allendale, MI 49401, USA, and ^bCenter for Crystallographic Research, Department of Chemistry, Michigan State University, 578 S. Shaw Lane, East Lansing, MI, 48824, USA
^*Correspondence e-mail: ngassaf@gvsu.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 27 April 2016; accepted 2 May 2016; online 6 May 2016)

The title compound, C₁₂H₇Cl₃O₃S, was synthesized via a nucleophilic substitution reaction between phenol and 2,4,5-trichlorobenzenesulfonyl chloride. The two aryl rings are oriented gauche to one another around the sulfonate S—O bond, with a C—S—O—C torsion angle of −70.68 (16)°, and the two rings are inclined to one another by 72.40 (7)°. In the crystal, molecules are linked via various C—Cl⋯π interactions, forming ribbons propagating along [100]. Neighboring ribbons are linked by a weak C—Cl⋯π interaction, forming layers parallel to (010).

Keywords: crystal structure; sulfonate; C—Cl⋯π interactions.

CCDC reference: 1477649

1. Chemical context

The use of arene-sulfonates as leaving groups has been explored in synthetic organic chemistry for quite some time (Crossland et al., 1971 ; Klán et al., 2013 ; Sardzinski et al., 2015 ). The stability of sulfonate ester leaving groups and the identification of suitable protecting groups for sulfonates has been reported (Miller, 2010 ). A competitive C—O and S—O bond fission has been reported in the reaction of amine nucleophiles with arene-sulfonates (Um et al., 2004 ). The basicity of the amine nucleophile and the electronic nature of the substituent on the sulfonyl moiety are responsible for the difference in regioselectivity. We have synthesized various arene-sulfonate analogues in order to investigate the factors responsible for the competition between C—O and S—O bond fission in the reaction with nitrogen nucleophiles (Atanasova et al., 2015 ; Cooley et al., 2015 ).

The sulfonamide moiety has found many useful applications in medicinal chemistry (Navia, 2000 ). Sulfonamides can be synthesized conveniently from the corresponding sulfonyl chloride and amine nucleophiles. In our recent work, we reported on the synthesis and crystal structure of a chiral sulfonamide (Ngassa et al., 2015 ). The direct synthesis of sulfonamides from arene-sulfonates has been reported (Caddick et al., 2004 ). Taking advantage of the regioselectivity of C—O vs S—O bond fission, we have explored the use of arene-sulfonates as electrophilic substrates in the synthesis of sulfonamides. We are interested in the role of the substituent on the sulfonyl moiety and the basicity of the amine nucleophile on the nucleophilic substitution. As the title compound is of interest in our ongoing effort to investigate the role of the substituent on the sulfonyl moiety in nucleophilic substitution reactions with nitrogen- and oxygen-nucleophiles, we report herein on the synthesis and crystal structure of this electrophilic arene-sulfonate.

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The two aryl rings are oriented gauche to one another around the sulfonate S1—O1 bond, with a C1—S1—O1—C7 torsion angle of −70.68 (16)°. The two rings (C1–C6 and C7–C12) are inclined to one another by 72.40 (7)°.

Figure 1
The molecular structure of the title compound, showing the atom labeling. Displacement ellipsoids are drawn at the 50% probability level.

3. Supramolecular features

In the crystal, molecules are linked by Cl⋯π interactions (Table 1 and Fig. 2). These intermolecular interactions range in Cl⋯ring centroid distances from 3.525 (1) to 3.972 (1) Å (Table 1). This distance falls near the accepted average as previously noted (Imai, et al., 2008 ), and all interactions have a `face-on' geometry. The two strong interactions involving atoms Cl1 and Cl2 with the centroid of ring C7–C12 form ribbons propagating along the a-axis direction. Within the ribbon there is also a weaker Cl⋯π interaction involving atom Cl3 and the centroid of ring C1–C6. Neighbouring ribbons are linked by a second weak Cl1⋯π interaction (Table 1 and Fig. 2), forming layers parallel to the ac plane. There are no other significant intermolecular interactions present in the crystal.

Table 1
Geometric parameters (Å, °) for C—Cl⋯π contacts in the title compound.

Cg 1 and Cg2 are the centroids of rings C1–C6 and C7–C12, respectively.

C—Cl⋯Cg	C—Cl	Cl⋯Cg	C⋯Cg	C—Cl⋯Cg
C2—Cl1⋯Cg2ⁱ	1.727 (2)	3.5250 (10)	5.028 (2)	144.23 (7)
C4—Cl2⋯Cg2ⁱⁱ	1.721 (2)	3.7914 (11)	5.160 (2)	135.37 (7)
C5—Cl3⋯Cg1ⁱⁱ	1.725 (2)	3.6298 (10)	4.211 (2)	97.25 (7)
C2—Cl1..Cg1ⁱⁱⁱ	1.727 (2)	3.9722 (10)	4.989 (2)	116.56 (7)
Symmetry codes:(i) −x + 2, −y + 1, −z + 1; (ii) −x + 1, −y + 2, −z + 1; (iii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ .

Figure 2
A view of the various C—Cl⋯π interactions (blue dashed lines; see Table 1

) present in the crystal lattice of the title compound. H atoms have been omitted for clarity [symmetry codes: (i) −x + 2, −y + 1, −z + 1; (ii) −x + 1, −y + 2, −z + 1; (iii) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{3\over 2}]$ ].

4. Database survey

The Cambridge Structural Database (CSD, Version 5.37, February 2016; Groom et al., 2016 ) contains eight structures of phenyl sulfonates where the group bonded directly to the sulfur atom is an aromatic ring. Other substituents on this ring include p-tolyl (FIQCIS: Manivannan et al., 2005 ), nitro (AJIWUL: Vembu et al., 2003 ; XUKBOV: Vembu & Fronczek, 2009 ), napthyl (VOJBOM: Vennila et al., 2008 ) and amino-napthyl (LEZWAP: Beyeh et al., 2007 ). Of particular interest is the structure JEGWEY (Wright et al., 2006 ) where the substituted aromatic ring bears chlorine atoms in the 2- and 5-positions. The torsion angle around the sulfonate S—O bond is 73.15 (19)°, similar to that seen in the title compound [70.68 (16)°]. In the crystal of this compound, one C—Cl⋯π interaction is present [Cl⋯π distance: 3.4187 (16) Å] along with C—H⋯O hydrogen bonds.

Two recent publications describing the crystal structures of benzopyrimidoazepine derivatives have also noted C—Cl⋯π interactions present in the lattice (Acosta et al., 2015 ; Acosta Quintero et al., 2016 ). In these examples, the C—Cl⋯π interactions are complemented by either C—H⋯π or π–π interactions between molecules in the solid state.

5. Synthesis and crystallization

Phenol (0.941g, 10 mmol) was dissolved in 10 ml of chilled dichloromethane. This was followed by the addition of pyridine (1.6 ml, 20 mmol). The resulting solution was cooled in an ice bath under an N₂ atmosphere, followed by the addition of 2,4,5-trichlorobenzenesulfonyl chloride (1.91 g, 10 mmol) portion-wise. The mixture was stirred at 273 K for 30 min and then at room temperature for 12 h. Reaction completion was verified by using TLC analysis. After dilution with 15 ml of CH₂Cl₂, the organic phase was washed with H₂O, brine, and dried over anhydrous Na₂SO₄. After the solvent was evaporated the crude product was obtained as a tan solid. The title compound was recrystallized from CH₂Cl₂/hexanes to afford colourless needle-like crystals (56% yield, m.p. 380–381 K) suitable for X-ray diffraction analysis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The positions of all hydrogen atoms were calculated geometrically and refined to ride on their parent atoms: C—H = 0. 95 Å with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₇Cl₃O₃S
M_r	337.59
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	12.3401 (11), 6.5421 (6), 16.1350 (14)
β (°)	92.1159 (10)
V (Å³)	1301.7 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.86
Crystal size (mm)	0.24 × 0.18 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.689, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	10912, 2568, 2172
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.06
No. of reflections	2568
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.28
Computer programs: APEX2 (Bruker, 2013), SAINT (Bruker, 2013), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), OLEX2 (Dolomanov et al., 2009 ; Bourhis et al., 2015 ), CrystalMaker (Palmer, 2007 ).

Supporting information

CCDC reference: 1477649

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989016007325/su5297sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016007325/su5297Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989016007325/su5297Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009; Bourhis et al., 2015); software used to prepare material for publication: CrystalMaker (Palmer, 2007).

Phenyl 2,4,5-trichlorobenzenesulfonate top

Crystal data top

C₁₂H₇Cl₃O₃S	F(000) = 680
M_r = 337.59	D_x = 1.723 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.3401 (11) Å	Cell parameters from 5969 reflections
b = 6.5421 (6) Å	θ = 2.5–26.0°
c = 16.1350 (14) Å	µ = 0.86 mm⁻¹
β = 92.1159 (10)°	T = 173 K
V = 1301.7 (2) Å³	Needle, colourless
Z = 4	0.24 × 0.18 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	2172 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.029
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 26.1°, θ_min = 2.0°
T_min = 0.689, T_max = 0.745	h = −15→15
10912 measured reflections	k = −8→8
2568 independent reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H-atom parameters constrained
wR(F²) = 0.083	w = 1/[σ²(F_o²) + (0.0396P)² + 0.7507P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2568 reflections	Δρ_max = 0.26 e Å⁻³
172 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cl3	0.40330 (4)	0.76082 (9)	0.56242 (3)	0.03498 (15)
Cl2	0.43839 (5)	1.20119 (9)	0.64173 (4)	0.04126 (17)
Cl1	0.86246 (4)	1.05869 (8)	0.68164 (3)	0.03599 (16)
S1	0.83040 (4)	0.61521 (8)	0.58959 (3)	0.02676 (14)
O2	0.78797 (12)	0.4493 (2)	0.54149 (9)	0.0322 (3)
O3	0.88861 (13)	0.5784 (2)	0.66557 (9)	0.0367 (4)
C1	0.72261 (16)	0.7865 (3)	0.60570 (12)	0.0250 (4)
C12	0.86103 (16)	0.9951 (3)	0.43502 (13)	0.0297 (5)
H12	0.8568	1.0940	0.4779	0.036*
O1	0.91219 (11)	0.7437 (2)	0.53709 (8)	0.0283 (3)
C3	0.64884 (17)	1.1015 (3)	0.65532 (12)	0.0287 (5)
H3	0.6587	1.2317	0.6806	0.034*
C6	0.61918 (16)	0.7233 (3)	0.58012 (12)	0.0260 (4)
H6	0.6093	0.5947	0.5535	0.031*
C8	0.89316 (17)	0.6461 (3)	0.39295 (13)	0.0309 (5)
H8	0.9107	0.5088	0.4072	0.037*
C5	0.53069 (16)	0.8467 (3)	0.59320 (12)	0.0267 (4)
C4	0.54605 (17)	1.0382 (3)	0.62926 (12)	0.0285 (5)
C2	0.73697 (17)	0.9755 (3)	0.64467 (12)	0.0273 (4)
C7	0.88520 (16)	0.7940 (3)	0.45289 (12)	0.0256 (4)
C10	0.84980 (18)	0.9035 (4)	0.29115 (13)	0.0352 (5)
H10	0.8371	0.9415	0.2348	0.042*
C11	0.84316 (18)	1.0485 (3)	0.35269 (14)	0.0345 (5)
H11	0.8262	1.1860	0.3385	0.041*
C9	0.87469 (18)	0.7041 (4)	0.31090 (14)	0.0359 (5)
H9	0.8793	0.6053	0.2680	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl3	0.0269 (3)	0.0401 (3)	0.0379 (3)	0.0003 (2)	0.0017 (2)	0.0008 (2)
Cl2	0.0432 (3)	0.0361 (3)	0.0451 (3)	0.0146 (2)	0.0111 (3)	0.0001 (2)
Cl1	0.0383 (3)	0.0317 (3)	0.0375 (3)	−0.0058 (2)	−0.0056 (2)	−0.0032 (2)
S1	0.0288 (3)	0.0241 (3)	0.0275 (3)	0.0027 (2)	0.0018 (2)	0.0006 (2)
O2	0.0345 (8)	0.0237 (8)	0.0386 (8)	−0.0003 (6)	0.0043 (6)	−0.0037 (6)
O3	0.0419 (9)	0.0386 (9)	0.0295 (8)	0.0100 (7)	−0.0021 (7)	0.0046 (7)
C1	0.0287 (11)	0.0228 (10)	0.0235 (10)	0.0032 (8)	0.0033 (8)	0.0015 (8)
C12	0.0290 (11)	0.0256 (11)	0.0347 (11)	−0.0001 (9)	0.0044 (9)	−0.0039 (9)
O1	0.0244 (7)	0.0334 (8)	0.0271 (7)	−0.0018 (6)	0.0002 (6)	0.0006 (6)
C3	0.0420 (12)	0.0232 (10)	0.0210 (10)	0.0007 (9)	0.0046 (9)	0.0001 (8)
C6	0.0296 (11)	0.0245 (10)	0.0241 (10)	0.0000 (8)	0.0042 (8)	0.0001 (8)
C8	0.0299 (11)	0.0287 (11)	0.0344 (11)	0.0034 (9)	0.0048 (9)	−0.0034 (9)
C5	0.0281 (10)	0.0285 (11)	0.0236 (10)	0.0006 (8)	0.0035 (8)	0.0029 (8)
C4	0.0354 (11)	0.0266 (11)	0.0239 (10)	0.0073 (9)	0.0088 (8)	0.0042 (8)
C2	0.0347 (11)	0.0247 (10)	0.0226 (10)	−0.0043 (9)	0.0011 (8)	0.0006 (8)
C7	0.0212 (10)	0.0305 (11)	0.0251 (10)	−0.0006 (8)	0.0022 (8)	0.0005 (8)
C10	0.0323 (12)	0.0458 (14)	0.0275 (11)	−0.0051 (10)	0.0022 (9)	0.0029 (10)
C11	0.0339 (12)	0.0301 (12)	0.0394 (12)	−0.0003 (9)	−0.0001 (10)	0.0066 (10)
C9	0.0371 (12)	0.0393 (13)	0.0316 (11)	−0.0027 (10)	0.0055 (9)	−0.0108 (10)

Geometric parameters (Å, º) top

Cl3—C5	1.725 (2)	C3—C4	1.385 (3)
Cl2—C4	1.721 (2)	C3—C2	1.380 (3)
Cl1—C2	1.727 (2)	C6—H6	0.9500
S1—O2	1.4229 (15)	C6—C5	1.380 (3)
S1—O3	1.4184 (15)	C8—H8	0.9500
S1—C1	1.766 (2)	C8—C7	1.374 (3)
S1—O1	1.5828 (15)	C8—C9	1.388 (3)
C1—C6	1.390 (3)	C5—C4	1.391 (3)
C1—C2	1.395 (3)	C10—H10	0.9500
C12—H12	0.9500	C10—C11	1.378 (3)
C12—C7	1.377 (3)	C10—C9	1.375 (3)
C12—C11	1.383 (3)	C11—H11	0.9500
O1—C7	1.425 (2)	C9—H9	0.9500
C3—H3	0.9500

O2—S1—C1	107.48 (9)	C6—C5—Cl3	118.90 (16)
O2—S1—O1	110.01 (8)	C6—C5—C4	119.61 (19)
O3—S1—O2	120.41 (9)	C4—C5—Cl3	121.47 (16)
O3—S1—C1	109.92 (9)	C3—C4—Cl2	118.78 (16)
O3—S1—O1	103.89 (9)	C3—C4—C5	120.35 (19)
O1—S1—C1	103.92 (9)	C5—C4—Cl2	120.87 (17)
C6—C1—S1	117.13 (15)	C1—C2—Cl1	122.17 (16)
C6—C1—C2	119.83 (19)	C3—C2—Cl1	117.99 (16)
C2—C1—S1	123.01 (16)	C3—C2—C1	119.84 (19)
C7—C12—H12	121.1	C12—C7—O1	117.49 (18)
C7—C12—C11	117.9 (2)	C8—C7—C12	123.09 (19)
C11—C12—H12	121.1	C8—C7—O1	119.19 (18)
C7—O1—S1	120.10 (12)	C11—C10—H10	119.8
C4—C3—H3	120.0	C9—C10—H10	119.8
C2—C3—H3	120.0	C9—C10—C11	120.3 (2)
C2—C3—C4	120.04 (19)	C12—C11—H11	119.8
C1—C6—H6	119.9	C10—C11—C12	120.4 (2)
C5—C6—C1	120.24 (19)	C10—C11—H11	119.8
C5—C6—H6	119.9	C8—C9—H9	119.7
C7—C8—H8	121.1	C10—C9—C8	120.5 (2)
C7—C8—C9	117.7 (2)	C10—C9—H9	119.7
C9—C8—H8	121.1

Cl3—C5—C4—Cl2	−2.0 (2)	C6—C1—C2—Cl1	177.38 (15)
Cl3—C5—C4—C3	178.38 (15)	C6—C1—C2—C3	−2.0 (3)
S1—C1—C6—C5	177.92 (15)	C6—C5—C4—Cl2	176.71 (15)
S1—C1—C2—Cl1	−0.5 (3)	C6—C5—C4—C3	−2.9 (3)
S1—C1—C2—C3	−179.86 (15)	C4—C3—C2—Cl1	−177.78 (15)
S1—O1—C7—C12	109.03 (18)	C4—C3—C2—C1	1.6 (3)
S1—O1—C7—C8	−76.3 (2)	C2—C1—C6—C5	−0.1 (3)
O2—S1—C1—C6	7.64 (18)	C2—C3—C4—Cl2	−178.78 (15)
O2—S1—C1—C2	−174.44 (16)	C2—C3—C4—C5	0.8 (3)
O2—S1—O1—C7	44.13 (16)	C7—C12—C11—C10	−0.1 (3)
O3—S1—C1—C6	−125.09 (16)	C7—C8—C9—C10	0.3 (3)
O3—S1—C1—C2	52.8 (2)	C11—C12—C7—O1	174.98 (18)
O3—S1—O1—C7	174.30 (14)	C11—C12—C7—C8	0.6 (3)
C1—S1—O1—C7	−70.68 (16)	C11—C10—C9—C8	0.2 (3)
C1—C6—C5—Cl3	−178.73 (15)	C9—C8—C7—C12	−0.6 (3)
C1—C6—C5—C4	2.5 (3)	C9—C8—C7—O1	−174.96 (18)
O1—S1—C1—C6	124.24 (15)	C9—C10—C11—C12	−0.2 (3)
O1—S1—C1—C2	−57.85 (18)

Geometric parameters (Å, °) for C—Cl···π contacts in the title compound. top

Cg 1 and Cg2 are the centroids of rings C1–C6 and C7–C12, respectively.

C—Cl···Cg	C—Cl	Cl···Cg	C···Cg	C—Cl···Cg
C2—Cl1···Cg2ⁱ	1.727 (2)	3.5250 (10)	5.028 (2)	144.23 (7)
C4—Cl2···Cg2ⁱⁱ	1.721 (2)	3.7914 (11)	5.160 (2)	135.37 (7)
C5—Cl3···Cg1ⁱⁱ	1.725 (2)	3.6298 (10)	4.211 (2)	97.25 (7)
C2—Cl1..Cg1ⁱⁱⁱ	1.727 (2)	3.9722 (10)	4.989 (2)	116.56 (7)

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

Acknowledgements

The authors thank GVSU for financial support (Weldon Fund, CSCE), the NSF for a 300 MHz Jeol FT–NMR (CCLI-0087655) and Pfizer, Inc. for the donation of a Varian Inova 400 F T NMR. The CCD-based X-ray diffractometers at Michigan State University were upgraded and/or replaced by departmental funds.

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