5-Methyl-1-[(4-methyl-phen-yl)sulfon-yl]-1H-pyrazol-3-yl 4-methyl-benzene-sulfonate.

In the title compound, C(18)H(18)N(2)O(5)S(2), the tolyl rings are oriented at a dihedral angle of 16.15 (11)° with respect to one another. The 5-methyl-1H-pyrazol-3-ol ring is roughly planar (r.m.s. deviation = 0.0231 Å) and subtends angles of 73.82 (8) and 89.85 (8)° with the tolyl rings. In the crystal, very weak π-π inter-actions between tolyl groups, with centroid-centroid distances of 4.1364 (19) and 4.0630 (16) Å, together with a C-H⋯π contact generate a three-dimensional network.

Related literature

For related structures, see: Gogoi et al. (2009 ▶); Murtaza et al. (2012 ▶).

Experimental

Crystal data

C18H18N2O5S2

M = 406.46

Monoclinic,

a = 22.296 (2) Å

b = 8.0444 (7) Å

c = 20.915 (2) Å

β = 98.521 (6)°

V = 3709.7 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.30 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.910, T max = 0.933

15506 measured reflections

4124 independent reflections

2548 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.128

S = 1.01

4124 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812027717/sj5243sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027717/sj5243Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027717/sj5243Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H18N2O5S2	F(000) = 1696
Mr = 406.46	Dx = 1.456 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2548 reflections
a = 22.296 (2) Å	θ = 1.9–27.2°
b = 8.0444 (7) Å	µ = 0.32 mm−1
c = 20.915 (2) Å	T = 296 K
β = 98.521 (6)°	Prism, white
V = 3709.7 (6) Å3	0.30 × 0.25 × 0.22 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	4124 independent reflections
Radiation source: fine-focus sealed tube	2548 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 7.80 pixels mm-1	θmax = 27.2°, θmin = 1.9°
ω scans	h = −28→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −10→10
Tmin = 0.910, Tmax = 0.933	l = −26→26
15506 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.6607P] where P = (Fo2 + 2Fc2)/3
4124 reflections	(Δ/σ)max = 0.001
247 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
S1	0.22735 (4)	0.04624 (9)	0.37485 (3)	0.0494 (3)
S2	0.06192 (3)	0.04283 (8)	0.11235 (3)	0.0429 (2)
O1	0.29151 (9)	0.0548 (3)	0.38078 (10)	0.0662 (8)
O2	0.19810 (11)	−0.1021 (2)	0.38973 (10)	0.0691 (9)
O3	0.08101 (8)	0.1414 (2)	0.17980 (9)	0.0460 (7)
O4	0.11514 (9)	0.0014 (2)	0.08671 (10)	0.0550 (7)
O5	0.01762 (9)	0.1490 (2)	0.07870 (10)	0.0614 (8)
N1	0.20378 (10)	0.0816 (3)	0.29509 (10)	0.0418 (8)
N2	0.14243 (10)	0.0735 (3)	0.27469 (11)	0.0421 (8)
C1	0.19849 (13)	0.2141 (3)	0.41327 (12)	0.0435 (9)
C2	0.22831 (14)	0.3644 (4)	0.41528 (14)	0.0540 (11)
C3	0.20366 (17)	0.4966 (4)	0.44373 (16)	0.0641 (13)
C4	0.15110 (16)	0.4839 (4)	0.46975 (14)	0.0571 (11)
C5	0.12313 (15)	0.3307 (4)	0.46813 (14)	0.0610 (11)
C6	0.14649 (14)	0.1940 (4)	0.44013 (13)	0.0529 (11)
C7	0.12476 (17)	0.6330 (4)	0.49855 (16)	0.0890 (16)
C8	0.23506 (12)	0.1375 (3)	0.24822 (14)	0.0439 (9)
C9	0.30235 (13)	0.1595 (5)	0.25488 (17)	0.0719 (14)
C10	0.19296 (12)	0.1638 (3)	0.19549 (14)	0.0476 (10)
C11	0.13808 (12)	0.1233 (3)	0.21468 (13)	0.0365 (9)
C12	0.02738 (11)	−0.1363 (3)	0.13625 (12)	0.0370 (8)
C13	0.05269 (12)	−0.2897 (3)	0.12767 (13)	0.0452 (9)
C14	0.02264 (14)	−0.4301 (3)	0.14397 (13)	0.0489 (10)
C15	−0.03075 (13)	−0.4199 (3)	0.16949 (13)	0.0439 (9)
C16	−0.05397 (13)	−0.2635 (4)	0.17760 (15)	0.0525 (11)
C17	−0.02588 (12)	−0.1226 (3)	0.16106 (14)	0.0498 (10)
C18	−0.06254 (15)	−0.5728 (4)	0.18785 (15)	0.0629 (11)
H2	0.26411	0.37592	0.39787	0.0648*
H3	0.22345	0.59864	0.44537	0.0767*
H5	0.08773	0.31896	0.48629	0.0733*
H6	0.12740	0.09105	0.43955	0.0635*
H7A	0.15676	0.69601	0.52314	0.1338*
H7B	0.09666	0.59725	0.52636	0.1338*
H7C	0.10402	0.70111	0.46458	0.1338*
H9A	0.31306	0.19893	0.21475	0.1079*
H9B	0.32195	0.05485	0.26575	0.1079*
H9C	0.31521	0.23876	0.28843	0.1079*
H10	0.19958	0.20108	0.15503	0.0571*
H13	0.08914	−0.29844	0.11129	0.0542*
H14	0.03888	−0.53417	0.13754	0.0585*
H16	−0.08991	−0.25389	0.19489	0.0630*
H17	−0.04267	−0.01866	0.16655	0.0597*
H18A	−0.04291	−0.66955	0.17383	0.0943*
H18B	−0.10407	−0.57056	0.16754	0.0943*
H18C	−0.06101	−0.57620	0.23394	0.0943*

	U11	U22	U33	U12	U13	U23
S1	0.0648 (6)	0.0397 (4)	0.0433 (4)	0.0083 (4)	0.0063 (4)	0.0018 (3)
S2	0.0445 (4)	0.0383 (4)	0.0456 (4)	−0.0034 (3)	0.0055 (3)	0.0012 (3)
O1	0.0546 (14)	0.0807 (16)	0.0598 (14)	0.0248 (12)	−0.0034 (11)	−0.0045 (12)
O2	0.1157 (19)	0.0378 (12)	0.0559 (13)	−0.0012 (12)	0.0201 (13)	0.0062 (10)
O3	0.0365 (11)	0.0416 (11)	0.0582 (12)	0.0028 (9)	0.0017 (9)	−0.0106 (9)
O4	0.0536 (13)	0.0568 (12)	0.0595 (13)	−0.0117 (10)	0.0242 (10)	−0.0075 (10)
O5	0.0614 (14)	0.0494 (12)	0.0672 (13)	0.0001 (10)	−0.0109 (11)	0.0170 (10)
N1	0.0385 (14)	0.0469 (14)	0.0401 (12)	−0.0011 (10)	0.0059 (11)	0.0008 (10)
N2	0.0385 (14)	0.0420 (13)	0.0472 (13)	−0.0038 (10)	0.0108 (11)	−0.0029 (10)
C1	0.0525 (19)	0.0386 (15)	0.0381 (14)	0.0019 (13)	0.0029 (13)	0.0020 (12)
C2	0.057 (2)	0.0473 (18)	0.0584 (18)	−0.0057 (15)	0.0110 (15)	0.0004 (15)
C3	0.088 (3)	0.0406 (18)	0.062 (2)	0.0000 (17)	0.006 (2)	−0.0058 (15)
C4	0.076 (2)	0.054 (2)	0.0385 (15)	0.0171 (18)	−0.0003 (16)	−0.0036 (14)
C5	0.065 (2)	0.077 (2)	0.0431 (16)	0.0067 (18)	0.0148 (15)	−0.0024 (16)
C6	0.064 (2)	0.0512 (19)	0.0443 (16)	−0.0074 (15)	0.0105 (15)	0.0002 (14)
C7	0.124 (3)	0.079 (3)	0.061 (2)	0.044 (2)	0.004 (2)	−0.015 (2)
C8	0.0373 (17)	0.0417 (16)	0.0534 (16)	−0.0076 (13)	0.0095 (14)	0.0074 (13)
C9	0.040 (2)	0.097 (3)	0.080 (2)	−0.0111 (18)	0.0128 (17)	0.018 (2)
C10	0.0427 (18)	0.0506 (18)	0.0497 (17)	−0.0090 (14)	0.0071 (14)	0.0124 (13)
C11	0.0338 (16)	0.0290 (14)	0.0473 (15)	−0.0018 (11)	0.0077 (12)	−0.0048 (12)
C12	0.0335 (15)	0.0333 (14)	0.0438 (14)	−0.0009 (12)	0.0042 (12)	0.0002 (11)
C13	0.0416 (17)	0.0442 (16)	0.0522 (16)	0.0055 (13)	0.0149 (13)	−0.0022 (13)
C14	0.063 (2)	0.0357 (16)	0.0491 (16)	0.0035 (14)	0.0120 (15)	−0.0033 (13)
C15	0.0488 (18)	0.0433 (16)	0.0387 (14)	−0.0092 (13)	0.0032 (13)	0.0009 (12)
C16	0.0391 (17)	0.0541 (19)	0.067 (2)	−0.0019 (15)	0.0167 (15)	0.0012 (15)
C17	0.0439 (18)	0.0376 (16)	0.070 (2)	0.0036 (13)	0.0156 (15)	−0.0027 (14)
C18	0.074 (2)	0.053 (2)	0.0589 (19)	−0.0227 (17)	0.0003 (17)	0.0030 (15)

S1—O1	1.419 (2)	C13—C14	1.382 (4)
S1—O2	1.416 (2)	C14—C15	1.377 (4)
S1—N1	1.697 (2)	C15—C16	1.381 (4)
S1—C1	1.743 (3)	C15—C18	1.498 (4)
S2—O3	1.6193 (19)	C16—C17	1.364 (4)
S2—O4	1.413 (2)	C2—H2	0.9300
S2—O5	1.412 (2)	C3—H3	0.9300
S2—C12	1.742 (3)	C5—H5	0.9300
O3—C11	1.378 (3)	C6—H6	0.9300
N1—N2	1.373 (3)	C7—H7A	0.9600
N1—C8	1.361 (4)	C7—H7B	0.9600
N2—C11	1.307 (4)	C7—H7C	0.9600
C1—C2	1.378 (4)	C9—H9A	0.9600
C1—C6	1.371 (4)	C9—H9B	0.9600
C2—C3	1.373 (5)	C9—H9C	0.9600
C3—C4	1.367 (5)	C10—H10	0.9300
C4—C5	1.379 (5)	C13—H13	0.9300
C4—C7	1.500 (5)	C14—H14	0.9300
C5—C6	1.383 (4)	C16—H16	0.9300
C8—C9	1.497 (4)	C17—H17	0.9300
C8—C10	1.355 (4)	C18—H18A	0.9600
C10—C11	1.382 (4)	C18—H18B	0.9600
C12—C13	1.380 (3)	C18—H18C	0.9600
C12—C17	1.369 (4)
O1—S1—O2	120.84 (14)	C14—C15—C18	121.3 (2)
O1—S1—N1	103.83 (12)	C16—C15—C18	121.1 (3)
O1—S1—C1	111.00 (14)	C15—C16—C17	122.1 (3)
O2—S1—N1	105.76 (12)	C12—C17—C16	119.1 (2)
O2—S1—C1	109.76 (13)	C1—C2—H2	121.00
N1—S1—C1	103.99 (12)	C3—C2—H2	121.00
O3—S2—O4	108.61 (11)	C2—C3—H3	119.00
O3—S2—O5	102.25 (11)	C4—C3—H3	119.00
O3—S2—C12	103.03 (11)	C4—C5—H5	119.00
O4—S2—O5	121.22 (12)	C6—C5—H5	119.00
O4—S2—C12	110.23 (11)	C1—C6—H6	121.00
O5—S2—C12	109.70 (12)	C5—C6—H6	121.00
S2—O3—C11	120.84 (16)	C4—C7—H7A	109.00
S1—N1—N2	116.53 (17)	C4—C7—H7B	109.00
S1—N1—C8	130.3 (2)	C4—C7—H7C	109.00
N2—N1—C8	112.7 (2)	H7A—C7—H7B	109.00
N1—N2—C11	102.3 (2)	H7A—C7—H7C	109.00
S1—C1—C2	119.0 (2)	H7B—C7—H7C	109.00
S1—C1—C6	119.4 (2)	C8—C9—H9A	109.00
C2—C1—C6	121.7 (3)	C8—C9—H9B	109.00
C1—C2—C3	118.1 (3)	C8—C9—H9C	109.00
C2—C3—C4	122.5 (3)	H9A—C9—H9B	109.00
C3—C4—C5	117.9 (3)	H9A—C9—H9C	109.00
C3—C4—C7	120.6 (3)	H9B—C9—H9C	109.00
C5—C4—C7	121.4 (3)	C8—C10—H10	127.00
C4—C5—C6	121.6 (3)	C11—C10—H10	127.00
C1—C6—C5	118.3 (3)	C12—C13—H13	121.00
N1—C8—C9	125.9 (3)	C14—C13—H13	121.00
N1—C8—C10	105.7 (2)	C13—C14—H14	119.00
C9—C8—C10	128.4 (3)	C15—C14—H14	119.00
C8—C10—C11	105.3 (2)	C15—C16—H16	119.00
O3—C11—N2	118.2 (2)	C17—C16—H16	119.00
O3—C11—C10	127.6 (2)	C12—C17—H17	120.00
N2—C11—C10	114.1 (2)	C16—C17—H17	120.00
S2—C12—C13	119.7 (2)	C15—C18—H18A	109.00
S2—C12—C17	119.17 (19)	C15—C18—H18B	109.00
C13—C12—C17	121.1 (2)	C15—C18—H18C	109.00
C12—C13—C14	118.5 (2)	H18A—C18—H18B	109.00
C13—C14—C15	121.7 (2)	H18A—C18—H18C	109.00
C14—C15—C16	117.6 (2)	H18B—C18—H18C	109.00
O1—S1—N1—N2	177.3 (2)	N2—N1—C8—C10	−1.1 (3)
O1—S1—N1—C8	−11.9 (3)	N1—N2—C11—O3	−175.7 (2)
O2—S1—N1—N2	49.2 (2)	N1—N2—C11—C10	−0.4 (3)
O2—S1—N1—C8	−140.0 (2)	S1—C1—C2—C3	177.7 (2)
C1—S1—N1—N2	−66.5 (2)	C6—C1—C2—C3	−1.6 (4)
C1—S1—N1—C8	104.4 (3)	S1—C1—C6—C5	−177.5 (2)
O1—S1—C1—C2	31.7 (3)	C2—C1—C6—C5	1.8 (4)
O1—S1—C1—C6	−148.9 (2)	C1—C2—C3—C4	0.0 (5)
O2—S1—C1—C2	167.9 (2)	C2—C3—C4—C5	1.4 (5)
O2—S1—C1—C6	−12.8 (3)	C2—C3—C4—C7	−178.1 (3)
N1—S1—C1—C2	−79.4 (2)	C3—C4—C5—C6	−1.2 (5)
N1—S1—C1—C6	100.0 (2)	C7—C4—C5—C6	178.3 (3)
O4—S2—O3—C11	−22.9 (2)	C4—C5—C6—C1	−0.4 (4)
O5—S2—O3—C11	−152.18 (18)	N1—C8—C10—C11	0.8 (3)
C12—S2—O3—C11	93.98 (19)	C9—C8—C10—C11	179.3 (3)
O3—S2—C12—C13	−116.7 (2)	C8—C10—C11—O3	174.6 (2)
O3—S2—C12—C17	65.8 (2)	C8—C10—C11—N2	−0.3 (3)
O4—S2—C12—C13	−0.9 (3)	S2—C12—C13—C14	−176.7 (2)
O4—S2—C12—C17	−178.5 (2)	C17—C12—C13—C14	0.8 (4)
O5—S2—C12—C13	135.0 (2)	S2—C12—C17—C16	177.7 (2)
O5—S2—C12—C17	−42.5 (3)	C13—C12—C17—C16	0.2 (4)
S2—O3—C11—N2	−123.4 (2)	C12—C13—C14—C15	−1.3 (4)
S2—O3—C11—C10	61.9 (3)	C13—C14—C15—C16	0.8 (4)
S1—N1—N2—C11	173.28 (18)	C13—C14—C15—C18	−179.2 (3)
C8—N1—N2—C11	0.9 (3)	C14—C15—C16—C17	0.2 (4)
S1—N1—C8—C9	9.3 (4)	C18—C15—C16—C17	−179.8 (3)
S1—N1—C8—C10	−172.1 (2)	C15—C16—C17—C12	−0.7 (5)
N2—N1—C8—C9	−179.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18b···Cg2i	0.96	2.66	3.471 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18b⋯Cg2i	0.96	2.66	3.471 (3)	142

Symmetry code: (i) .