1-Benzene­sulfonyl-5-chloro-2,4-dimethoxy­benzene

In the title compound, C₁₄H₁₃ClO₄S, the dihedral angle between the two benzene rings is 73.0 (2)°. The supra­molecular aggregation is completed by means of C—H...O hydrogen bonds involving a sulfone O atom and an aromatic CH group, forming centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.040
• wR factor = 0.107
• Data-to-parameter ratio = 16.3

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.

1-Benzenesulfonyl-5-chloro-2,4-dimethoxybenzene

Crystal data

C14H13ClO4S	F(000) = 1296
Mr = 312.75	Dx = 1.450 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3181 reflections
a = 7.3423 (16) Å	θ = 2.3–23.7°
b = 19.487 (4) Å	µ = 0.42 mm^−1
c = 20.022 (4) Å	T = 294 K
V = 2864.7 (10) Å^3	Prism, colourless
Z = 8	0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART-1000 CCD area-detector diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	1860 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
φ and ω scans	θmax = 26.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.898, Tmax = 0.921	k = −24→23
15348 measured reflections	l = −25→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0452P)^2 + 0.9214P] where P = (Fo^2 + 2Fc^2)/3
2981 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.33 e Å^−3

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

	x	y	z	Uiso*/Ueq
S1	0.74621 (9)	0.06892 (3)	0.41420 (3)	0.04242 (18)
Cl1	0.92833 (12)	−0.16835 (3)	0.29332 (4)	0.0665 (3)
O1	0.7704 (3)	0.02060 (9)	0.46753 (8)	0.0578 (5)
O2	0.5713 (2)	0.10069 (10)	0.40637 (8)	0.0559 (5)
O3	0.7602 (2)	0.12496 (8)	0.27749 (7)	0.0472 (5)
O4	0.8868 (2)	−0.09224 (8)	0.17075 (8)	0.0520 (5)
C1	0.9083 (3)	0.13456 (12)	0.42414 (11)	0.0410 (6)
C2	1.0727 (4)	0.11938 (14)	0.45485 (12)	0.0523 (7)
H2	1.0968	0.0752	0.4700	0.063*
C3	1.2003 (4)	0.17106 (18)	0.46257 (15)	0.0677 (9)
H3	1.3104	0.1620	0.4837	0.081*
C4	1.1639 (5)	0.23599 (17)	0.43894 (16)	0.0746 (9)
H4	1.2509	0.2703	0.4436	0.090*
C5	1.0010 (5)	0.25072 (15)	0.40856 (14)	0.0648 (8)
H5	0.9780	0.2948	0.3929	0.078*
C6	0.8715 (4)	0.20004 (13)	0.40123 (12)	0.0504 (7)
H6	0.7604	0.2098	0.3811	0.061*
C7	0.8022 (3)	0.02489 (11)	0.34001 (11)	0.0373 (6)
C8	0.7948 (3)	0.05660 (11)	0.27752 (11)	0.0356 (5)
C9	0.8236 (3)	0.01836 (11)	0.22011 (11)	0.0374 (6)
H9	0.8180	0.0395	0.1785	0.045*
C10	0.8606 (3)	−0.05105 (12)	0.22430 (11)	0.0392 (6)
C11	0.8742 (3)	−0.08203 (11)	0.28706 (12)	0.0410 (6)
C12	0.8438 (3)	−0.04436 (12)	0.34382 (11)	0.0402 (6)
H12	0.8511	−0.0655	0.3854	0.048*
C13	0.7655 (4)	0.16126 (13)	0.21577 (12)	0.0519 (7)
H13A	0.8809	0.1537	0.1945	0.078*
H13B	0.7495	0.2094	0.2240	0.078*
H13C	0.6696	0.1451	0.1872	0.078*
C14	0.8444 (4)	−0.06548 (13)	0.10585 (12)	0.0545 (7)
H14A	0.7218	−0.0484	0.1057	0.082*
H14B	0.8560	−0.1013	0.0732	0.082*
H14C	0.9270	−0.0289	0.0952	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0516 (4)	0.0471 (4)	0.0286 (3)	0.0061 (3)	0.0028 (3)	0.0012 (3)
Cl1	0.0966 (6)	0.0342 (3)	0.0687 (5)	0.0078 (4)	−0.0029 (4)	0.0033 (3)
O1	0.0829 (14)	0.0584 (11)	0.0320 (9)	0.0043 (10)	0.0060 (9)	0.0082 (8)
O2	0.0487 (11)	0.0674 (12)	0.0517 (11)	0.0117 (9)	0.0051 (9)	−0.0071 (9)
O3	0.0753 (13)	0.0360 (9)	0.0302 (9)	0.0098 (8)	−0.0010 (8)	0.0009 (7)
O4	0.0763 (13)	0.0416 (10)	0.0382 (10)	0.0057 (9)	−0.0018 (9)	−0.0088 (8)
C1	0.0500 (15)	0.0455 (14)	0.0275 (12)	0.0088 (12)	−0.0009 (11)	−0.0072 (10)
C2	0.0632 (18)	0.0555 (16)	0.0383 (15)	0.0137 (14)	−0.0093 (13)	−0.0074 (12)
C3	0.060 (2)	0.081 (2)	0.062 (2)	0.0067 (18)	−0.0143 (15)	−0.0225 (17)
C4	0.083 (2)	0.065 (2)	0.075 (2)	−0.0169 (19)	0.0024 (19)	−0.0262 (17)
C5	0.091 (2)	0.0446 (16)	0.059 (2)	0.0017 (17)	−0.0019 (17)	−0.0128 (13)
C6	0.0633 (19)	0.0444 (15)	0.0437 (15)	0.0107 (13)	−0.0040 (13)	−0.0087 (12)
C7	0.0406 (15)	0.0392 (13)	0.0321 (13)	0.0014 (10)	0.0005 (10)	−0.0009 (10)
C8	0.0401 (14)	0.0345 (13)	0.0323 (12)	0.0042 (10)	−0.0016 (10)	−0.0006 (10)
C9	0.0426 (14)	0.0401 (13)	0.0296 (12)	0.0006 (11)	−0.0024 (10)	0.0028 (10)
C10	0.0428 (15)	0.0386 (13)	0.0362 (13)	−0.0018 (11)	−0.0005 (10)	−0.0045 (10)
C11	0.0457 (15)	0.0306 (12)	0.0466 (15)	−0.0005 (10)	−0.0033 (11)	0.0012 (11)
C12	0.0464 (15)	0.0390 (13)	0.0353 (13)	−0.0009 (11)	−0.0014 (11)	0.0070 (11)
C13	0.076 (2)	0.0393 (14)	0.0400 (15)	0.0108 (13)	0.0014 (13)	0.0077 (11)
C14	0.078 (2)	0.0497 (16)	0.0364 (14)	0.0018 (15)	−0.0038 (13)	−0.0089 (12)

Geometric parameters (Å, º)

S1—O2	1.4342 (19)	C5—C6	1.379 (4)
S1—O1	1.4348 (17)	C5—H5	0.9300
S1—C1	1.758 (3)	C6—H6	0.9300
S1—C7	1.764 (2)	C7—C12	1.386 (3)
Cl1—C11	1.733 (2)	C7—C8	1.397 (3)
O3—C8	1.356 (3)	C8—C9	1.386 (3)
O3—C13	1.424 (3)	C9—C10	1.382 (3)
O4—C10	1.353 (3)	C9—H9	0.9300
O4—C14	1.434 (3)	C10—C11	1.398 (3)
C1—C6	1.383 (3)	C11—C12	1.371 (3)
C1—C2	1.387 (3)	C12—H12	0.9300
C2—C3	1.384 (4)	C13—H13A	0.9600
C2—H2	0.9300	C13—H13B	0.9600
C3—C4	1.377 (4)	C13—H13C	0.9600
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.372 (4)	C14—H14B	0.9600
C4—H4	0.9300	C14—H14C	0.9600
O2—S1—O1	118.38 (11)	C8—C7—S1	122.01 (17)
O2—S1—C1	107.73 (12)	O3—C8—C9	123.80 (19)
O1—S1—C1	108.03 (11)	O3—C8—C7	116.26 (19)
O2—S1—C7	109.06 (11)	C9—C8—C7	119.9 (2)
O1—S1—C7	106.18 (11)	C10—C9—C8	120.4 (2)
C1—S1—C7	106.94 (11)	C10—C9—H9	119.8
C8—O3—C13	118.89 (17)	C8—C9—H9	119.8
C10—O4—C14	118.11 (19)	O4—C10—C9	124.1 (2)
C6—C1—C2	120.9 (2)	O4—C10—C11	116.5 (2)
C6—C1—S1	120.1 (2)	C9—C10—C11	119.4 (2)
C2—C1—S1	119.0 (2)	C12—C11—C10	120.1 (2)
C3—C2—C1	118.9 (3)	C12—C11—Cl1	119.80 (18)
C3—C2—H2	120.6	C10—C11—Cl1	120.05 (18)
C1—C2—H2	120.6	C11—C12—C7	120.8 (2)
C4—C3—C2	119.9 (3)	C11—C12—H12	119.6
C4—C3—H3	120.0	C7—C12—H12	119.6
C2—C3—H3	120.0	O3—C13—H13A	109.5
C5—C4—C3	120.9 (3)	O3—C13—H13B	109.5
C5—C4—H4	119.5	H13A—C13—H13B	109.5
C3—C4—H4	119.5	O3—C13—H13C	109.5
C4—C5—C6	119.9 (3)	H13A—C13—H13C	109.5
C4—C5—H5	120.1	H13B—C13—H13C	109.5
C6—C5—H5	120.1	O4—C14—H14A	109.5
C5—C6—C1	119.4 (3)	O4—C14—H14B	109.5
C5—C6—H6	120.3	H14A—C14—H14B	109.5
C1—C6—H6	120.3	O4—C14—H14C	109.5
C12—C7—C8	119.3 (2)	H14A—C14—H14C	109.5
C12—C7—S1	118.61 (17)	H14B—C14—H14C	109.5
O2—S1—C1—C6	−22.3 (2)	C13—O3—C8—C9	−4.4 (4)
O1—S1—C1—C6	−151.29 (19)	C13—O3—C8—C7	175.0 (2)
C7—S1—C1—C6	94.8 (2)	C12—C7—C8—O3	−177.6 (2)
O2—S1—C1—C2	157.99 (19)	S1—C7—C8—O3	6.5 (3)
O1—S1—C1—C2	29.0 (2)	C12—C7—C8—C9	1.9 (3)
C7—S1—C1—C2	−84.9 (2)	S1—C7—C8—C9	−174.03 (18)
C6—C1—C2—C3	0.2 (4)	O3—C8—C9—C10	179.1 (2)
S1—C1—C2—C3	179.9 (2)	C7—C8—C9—C10	−0.3 (4)
C1—C2—C3—C4	−1.0 (4)	C14—O4—C10—C9	−10.8 (4)
C2—C3—C4—C5	1.0 (5)	C14—O4—C10—C11	169.8 (2)
C3—C4—C5—C6	−0.2 (5)	C8—C9—C10—O4	178.7 (2)
C4—C5—C6—C1	−0.6 (4)	C8—C9—C10—C11	−1.9 (4)
C2—C1—C6—C5	0.6 (4)	O4—C10—C11—C12	−177.9 (2)
S1—C1—C6—C5	−179.1 (2)	C9—C10—C11—C12	2.7 (4)
O2—S1—C7—C12	−124.3 (2)	O4—C10—C11—Cl1	1.7 (3)
O1—S1—C7—C12	4.3 (2)	C9—C10—C11—Cl1	−177.76 (19)
C1—S1—C7—C12	119.5 (2)	C10—C11—C12—C7	−1.1 (4)
O2—S1—C7—C8	51.7 (2)	Cl1—C11—C12—C7	179.32 (18)
O1—S1—C7—C8	−179.73 (19)	C8—C7—C12—C11	−1.2 (4)
C1—S1—C7—C8	−64.6 (2)	S1—C7—C12—C11	174.87 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1^i	0.93	2.45	3.344 (5)	162

Symmetry code: (i) −x+2, −y, −z+1.