Crystal structure of 2-[(di­chloro­methane)sulfon­yl]pyridine

Chen, Z.; Bolat, H.; Wan, X.; Li, Y.

doi:10.1107/S1600536814025148

organic compounds

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Volume 70| Part 12| December 2014| Page o1272

doi:10.1107/S1600536814025148

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Crystal structure of 2-[(dichloromethane)sulfonyl]pyridine

Zhiqiu Chen,^a Hembat Bolat,^a Xing Wan ^a and Ya Li ^a ^*

^aCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, 333 Longteng Road, Shanghai, People's Republic of China
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 13 November 2014; accepted 17 November 2014; online 21 November 2014)

The asymmetric unit of the title compound, C₆H₅Cl₂NO₂S, contains two molecules with similar conformations (r.m.s. overlay fit for the non-H atoms = 0.067 Å). Atoms attached to the pendent Csp³—S bond are arranged in a staggered conformation with one of the Cl atoms anti to the C atom in the aromatic ring [C—S—C—Cl torsion angles = 178.41 (11) and −176.70 (13)°]. In the crystal, molecules are linked by C—H⋯N and C—H⋯O hydrogen bonds, generating a three-dimensional network, and weak aromatic π–π stacking is also observed [centroid–centroid separation = 3.8902 (17) Å].

Keywords: crystal structure; sulfone; pyridine derivative; hydrogen bonding; π–π stacking.

CCDC reference: 1034519

1. Related literature

For the biological activity of sulfone derivatives, see: Chen et al. (2012 ); Drews (2000 ); Raja et al. (2009 ). For the uses of halomethyl sulfone derivatives in organic synthesis, see: Li & Hu (2005 ); Prakash et al. (2013 ); Zhao et al. (2010 ). For the synthesis of the starting material, see: Kamiyama et al. (1988 ).

2. Experimental

2.1. Crystal data

C₆H₅Cl₂NO₂S
M_r = 226.07
Monoclinic, P 2₁ /n
a = 9.9647 (10) Å
b = 12.2131 (11) Å
c = 15.7158 (15) Å
β = 108.483 (1)°
V = 1814.0 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 293 K
0.21 × 0.16 × 0.12 mm

2.2. Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.615, T_max = 0.746
10817 measured reflections
3570 independent reflections
2907 reflections with I > 2σ(I)
R_int = 0.034

2.3. Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.03
3570 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯N2ⁱ	0.98	2.37	3.321 (3)	163
C5—H5⋯O3ⁱⁱ	0.93	2.64	3.220 (3)	121
C6—H6⋯O3ⁱⁱ	0.93	2.54	3.177 (3)	126
C7—H7⋯N1ⁱ	0.98	2.36	3.303 (3)	162
C11—H11⋯O1ⁱⁱⁱ	0.93	2.64	3.292 (3)	128
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

CCDC reference: 1034519

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814025148/hb7316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814025148/hb7316Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814025148/hb7316Isup3.cml

checkCIF report

Comment top

Sulfonyl groups are well-known for imparting biological activities to a lot of natural and unnatural molecules (Chen, et al., 2012; Drews, 2000; Raja, et al., 2009). Besides, halomethyl sulfones have been widely used in the preparation of a wide variety of halogenated compounds (Li & Hu, 2005; Prakash, et al., 2013; Zhao, et al., 2010). Here, we report the crystal structure of 2-(dichloromethylsulfonyl)pyridine, the title compound, which may find potential use in the synthesis of interesting chlorinated compounds.

Experimental top

A mixture of sodium pyridine-2-sulfinate (660 mg, 4.0 mmol), chloroform (10.0 ml) and 1N KOH (5.0 ml) was refluxed over 5h. Then the orgainc layer was separated and dried over anhydrous MgSO₄. Evaporation of the solvent under vacuum, followed by flash chromatography, gave the title compound (white solid, 560 mg, 62 %). The obtained powder was recrystalized from ethyl acetate/hexane(1:10) solution to give colourless prisms.

Refinement top

The H atoms of the pyridine group were placed at calculated positions and treated as riding on the parent atoms, with Uiso(H) = 1.2Ueq(C). The dichloromethyl H atom was placed at calculated position with Uiso(H) = 1.2Ueq(C).

Related literature top

For the biological activity of sulfone derivatives, see: Chen et al. (2012); Drews (2000); Raja et al. (2009). For the uses of halomethyl sulfone derivatives in organic synthesis, see: Li & Hu (2005); Prakash et al. (2013); Zhao et al. (2010). For the synthesis of the starting material, see: Kamiyama et al. (1988).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Molecular structure of the title compound. The displacement ellipsoids are drawn at the 50% probability level.

2-[(Dichloromethane)sulfonyl]pyridine top

Crystal data top

C₆H₅Cl₂NO₂S	F(000) = 912
M_r = 226.07	D_x = 1.656 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.9647 (10) Å	Cell parameters from 4116 reflections
b = 12.2131 (11) Å	θ = 4.3–54.4°
c = 15.7158 (15) Å	µ = 0.90 mm⁻¹
β = 108.483 (1)°	T = 293 K
V = 1814.0 (3) Å³	Prism, colorless
Z = 8	0.21 × 0.16 × 0.12 mm

Data collection top

Bruker SMART CCD diffractometer	2907 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.034
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 26.0°, θ_min = 2.2°
T_min = 0.615, T_max = 0.746	h = −12→12
10817 measured reflections	k = −15→13
3570 independent reflections	l = −19→14

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.048P)² + 0.7592P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.102	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.37 e Å⁻³
3570 reflections	Δρ_min = −0.37 e Å⁻³
218 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2013), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0286 (15)

Crystal data top

C₆H₅Cl₂NO₂S	V = 1814.0 (3) Å³
M_r = 226.07	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.9647 (10) Å	µ = 0.90 mm⁻¹
b = 12.2131 (11) Å	T = 293 K
c = 15.7158 (15) Å	0.21 × 0.16 × 0.12 mm
β = 108.483 (1)°

Data collection top

Bruker SMART CCD diffractometer	3570 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2907 reflections with I > 2σ(I)
T_min = 0.615, T_max = 0.746	R_int = 0.034
10817 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.37 e Å⁻³
3570 reflections	Δρ_min = −0.37 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.22031 (6)	0.33604 (5)	0.12351 (4)	0.04809 (18)
S2	0.34445 (7)	0.72345 (5)	0.63426 (4)	0.05073 (19)
Cl1	0.13628 (8)	0.50108 (5)	0.23115 (5)	0.0676 (2)
Cl2	0.16196 (8)	0.27131 (5)	0.28379 (5)	0.0647 (2)
Cl3	0.19229 (9)	0.60561 (8)	0.73732 (6)	0.0850 (3)
Cl4	0.32582 (10)	0.81316 (7)	0.79958 (5)	0.0874 (3)
N1	0.4188 (2)	0.47686 (16)	0.13024 (13)	0.0499 (5)
N2	0.4604 (2)	0.53408 (16)	0.62759 (13)	0.0517 (5)
O1	0.0757 (2)	0.32158 (16)	0.07175 (13)	0.0733 (6)
O2	0.3169 (2)	0.24747 (14)	0.13497 (12)	0.0672 (5)
O3	0.2167 (2)	0.77708 (15)	0.58491 (13)	0.0734 (6)
O4	0.4775 (2)	0.77492 (15)	0.64783 (14)	0.0699 (5)
C1	0.2303 (2)	0.37906 (17)	0.23599 (15)	0.0447 (5)
H1	0.3296	0.3910	0.2713	0.054*
C2	0.2870 (2)	0.45238 (18)	0.08275 (14)	0.0429 (5)
C3	0.2047 (3)	0.5082 (2)	0.00872 (16)	0.0529 (6)
H3	0.1126	0.4864	−0.0220	0.064*
C4	0.2646 (3)	0.5977 (2)	−0.01787 (17)	0.0592 (6)
H4	0.2135	0.6385	−0.0675	0.071*
C5	0.4002 (3)	0.6258 (2)	0.02950 (19)	0.0607 (7)
H5	0.4425	0.6861	0.0123	0.073*
C6	0.4741 (3)	0.5646 (2)	0.10274 (18)	0.0578 (6)
H6	0.5663	0.5851	0.1345	0.069*
C7	0.3368 (3)	0.6905 (2)	0.74546 (16)	0.0523 (6)
H7	0.4239	0.6524	0.7792	0.063*
C8	0.3445 (2)	0.59091 (18)	0.58779 (15)	0.0454 (5)
C9	0.2333 (3)	0.5566 (2)	0.51689 (17)	0.0596 (6)
H9	0.1550	0.6010	0.4916	0.072*
C10	0.2428 (3)	0.4520 (2)	0.48428 (19)	0.0691 (8)
H10	0.1695	0.4238	0.4367	0.083*
C11	0.3620 (3)	0.3912 (2)	0.52340 (19)	0.0648 (7)
H11	0.3718	0.3217	0.5019	0.078*
C12	0.4667 (3)	0.4344 (2)	0.59470 (19)	0.0612 (7)
H12	0.5463	0.3918	0.6215	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0590 (4)	0.0370 (3)	0.0447 (3)	−0.0097 (2)	0.0115 (3)	−0.0018 (2)
S2	0.0659 (4)	0.0382 (3)	0.0499 (3)	0.0138 (3)	0.0209 (3)	0.0044 (2)
Cl1	0.0791 (5)	0.0434 (3)	0.0909 (5)	0.0082 (3)	0.0420 (4)	0.0000 (3)
Cl2	0.0849 (5)	0.0483 (4)	0.0719 (4)	−0.0087 (3)	0.0407 (4)	0.0051 (3)
Cl3	0.0800 (5)	0.1064 (7)	0.0806 (5)	−0.0173 (5)	0.0426 (4)	−0.0035 (5)
Cl4	0.1221 (7)	0.0714 (5)	0.0727 (5)	0.0256 (5)	0.0367 (5)	−0.0173 (4)
N1	0.0482 (11)	0.0488 (11)	0.0503 (11)	−0.0034 (9)	0.0123 (9)	0.0050 (9)
N2	0.0576 (12)	0.0422 (10)	0.0543 (11)	0.0135 (9)	0.0164 (9)	0.0040 (9)
O1	0.0736 (13)	0.0696 (12)	0.0613 (11)	−0.0329 (10)	−0.0005 (10)	0.0030 (9)
O2	0.1029 (15)	0.0415 (9)	0.0640 (11)	0.0094 (9)	0.0362 (11)	0.0002 (8)
O3	0.0935 (14)	0.0607 (11)	0.0617 (11)	0.0395 (10)	0.0183 (10)	0.0112 (9)
O4	0.0863 (14)	0.0513 (10)	0.0810 (13)	−0.0130 (9)	0.0390 (11)	−0.0032 (9)
C1	0.0474 (12)	0.0372 (11)	0.0512 (13)	−0.0037 (9)	0.0182 (10)	−0.0011 (9)
C2	0.0505 (13)	0.0383 (11)	0.0400 (11)	−0.0032 (9)	0.0145 (10)	−0.0009 (9)
C3	0.0541 (14)	0.0567 (14)	0.0444 (12)	0.0023 (11)	0.0104 (11)	0.0039 (11)
C4	0.0749 (18)	0.0531 (14)	0.0522 (14)	0.0128 (13)	0.0240 (13)	0.0148 (11)
C5	0.0749 (18)	0.0466 (13)	0.0696 (17)	−0.0037 (12)	0.0357 (15)	0.0081 (12)
C6	0.0539 (14)	0.0545 (14)	0.0655 (16)	−0.0086 (12)	0.0198 (12)	0.0043 (12)
C7	0.0574 (14)	0.0522 (13)	0.0493 (13)	0.0141 (11)	0.0195 (11)	0.0013 (11)
C8	0.0556 (13)	0.0390 (11)	0.0437 (12)	0.0071 (10)	0.0187 (10)	0.0023 (9)
C9	0.0640 (16)	0.0594 (15)	0.0512 (14)	0.0108 (12)	0.0124 (12)	0.0016 (12)
C10	0.083 (2)	0.0644 (17)	0.0554 (15)	−0.0077 (15)	0.0154 (14)	−0.0098 (13)
C11	0.093 (2)	0.0406 (13)	0.0681 (17)	0.0037 (13)	0.0359 (16)	−0.0039 (12)
C12	0.0751 (18)	0.0419 (13)	0.0687 (17)	0.0158 (12)	0.0259 (14)	0.0032 (12)

Geometric parameters (Å, º) top

S1—O2	1.4212 (19)	C2—C3	1.373 (3)
S1—O1	1.4235 (19)	C3—C4	1.372 (4)
S1—C2	1.772 (2)	C3—H3	0.9300
S1—C1	1.816 (2)	C4—C5	1.364 (4)
S2—O4	1.421 (2)	C4—H4	0.9300
S2—O3	1.4231 (19)	C5—C6	1.374 (4)
S2—C8	1.776 (2)	C5—H5	0.9300
S2—C7	1.818 (2)	C6—H6	0.9300
Cl1—C1	1.749 (2)	C7—H7	0.9800
Cl2—C1	1.756 (2)	C8—C9	1.364 (3)
Cl3—C7	1.746 (3)	C9—C10	1.390 (4)
Cl4—C7	1.743 (2)	C9—H9	0.9300
N1—C2	1.323 (3)	C10—C11	1.370 (4)
N1—C6	1.338 (3)	C10—H10	0.9300
N2—C8	1.323 (3)	C11—C12	1.371 (4)
N2—C12	1.332 (3)	C11—H11	0.9300
C1—H1	0.9800	C12—H12	0.9300

O2—S1—O1	120.03 (13)	C3—C4—H4	120.5
O2—S1—C2	109.84 (11)	C4—C5—C6	119.7 (2)
O1—S1—C2	108.69 (11)	C4—C5—H5	120.2
O2—S1—C1	105.72 (10)	C6—C5—H5	120.2
O1—S1—C1	108.98 (12)	N1—C6—C5	122.7 (2)
C2—S1—C1	102.05 (10)	N1—C6—H6	118.6
O4—S2—O3	120.59 (13)	C5—C6—H6	118.6
O4—S2—C8	110.07 (11)	Cl4—C7—Cl3	111.61 (13)
O3—S2—C8	108.19 (12)	Cl4—C7—S2	107.87 (13)
O4—S2—C7	105.97 (12)	Cl3—C7—S2	110.24 (13)
O3—S2—C7	108.84 (12)	Cl4—C7—H7	109.0
C8—S2—C7	101.49 (11)	Cl3—C7—H7	109.0
C2—N1—C6	115.8 (2)	S2—C7—H7	109.0
C8—N2—C12	116.0 (2)	N2—C8—C9	125.9 (2)
Cl1—C1—Cl2	112.46 (13)	N2—C8—S2	113.44 (17)
Cl1—C1—S1	109.92 (12)	C9—C8—S2	120.67 (18)
Cl2—C1—S1	106.89 (11)	C8—C9—C10	116.8 (2)
Cl1—C1—H1	109.2	C8—C9—H9	121.6
Cl2—C1—H1	109.2	C10—C9—H9	121.6
S1—C1—H1	109.2	C11—C10—C9	118.9 (3)
N1—C2—C3	125.8 (2)	C11—C10—H10	120.6
N1—C2—S1	113.34 (16)	C9—C10—H10	120.6
C3—C2—S1	120.84 (18)	C10—C11—C12	119.0 (2)
C4—C3—C2	116.9 (2)	C10—C11—H11	120.5
C4—C3—H3	121.5	C12—C11—H11	120.5
C2—C3—H3	121.5	N2—C12—C11	123.4 (2)
C5—C4—C3	119.1 (2)	N2—C12—H12	118.3
C5—C4—H4	120.5	C11—C12—H12	118.3

O2—S1—C1—Cl1	170.96 (12)	O4—S2—C7—Cl4	68.31 (15)
O1—S1—C1—Cl1	−58.75 (15)	O3—S2—C7—Cl4	−62.76 (16)
C2—S1—C1—Cl1	56.09 (14)	C8—S2—C7—Cl4	−176.70 (13)
O2—S1—C1—Cl2	−66.71 (14)	O4—S2—C7—Cl3	−169.59 (13)
O1—S1—C1—Cl2	63.58 (14)	O3—S2—C7—Cl3	59.34 (16)
C2—S1—C1—Cl2	178.41 (11)	C8—S2—C7—Cl3	−54.61 (15)
C6—N1—C2—C3	0.5 (4)	C12—N2—C8—C9	−0.3 (4)
C6—N1—C2—S1	−179.51 (18)	C12—N2—C8—S2	−179.28 (19)
O2—S1—C2—N1	−50.8 (2)	O4—S2—C8—N2	45.1 (2)
O1—S1—C2—N1	176.04 (17)	O3—S2—C8—N2	178.72 (18)
C1—S1—C2—N1	61.00 (19)	C7—S2—C8—N2	−66.86 (19)
O2—S1—C2—C3	129.1 (2)	O4—S2—C8—C9	−134.0 (2)
O1—S1—C2—C3	−4.0 (2)	O3—S2—C8—C9	−0.3 (2)
C1—S1—C2—C3	−119.0 (2)	C7—S2—C8—C9	114.1 (2)
N1—C2—C3—C4	−0.4 (4)	N2—C8—C9—C10	0.6 (4)
S1—C2—C3—C4	179.66 (18)	S2—C8—C9—C10	179.4 (2)
C2—C3—C4—C5	0.2 (4)	C8—C9—C10—C11	−1.1 (4)
C3—C4—C5—C6	−0.1 (4)	C9—C10—C11—C12	1.5 (4)
C2—N1—C6—C5	−0.5 (4)	C8—N2—C12—C11	0.7 (4)
C4—C5—C6—N1	0.3 (4)	C10—C11—C12—N2	−1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2ⁱ	0.98	2.37	3.321 (3)	163
C5—H5···O3ⁱⁱ	0.93	2.64	3.220 (3)	121
C6—H6···O3ⁱⁱ	0.93	2.54	3.177 (3)	126
C7—H7···N1ⁱ	0.98	2.36	3.303 (3)	162
C11—H11···O1ⁱⁱⁱ	0.93	2.64	3.292 (3)	128

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N2ⁱ	0.98	2.37	3.321 (3)	163
C5—H5···O3ⁱⁱ	0.93	2.64	3.220 (3)	121
C6—H6···O3ⁱⁱ	0.93	2.54	3.177 (3)	126
C7—H7···N1ⁱ	0.98	2.36	3.303 (3)	162
C11—H11···O1ⁱⁱⁱ	0.93	2.64	3.292 (3)	128

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

Acknowledgements

Financial support from the Innovation Program of the Shanghai University Students (cs1304009) is gratefully acknowledged.

References

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Volume 70| Part 12| December 2014| Page o1272

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