An unknown solvate of 1-(2,4-di-chloro-benz-yl)-4-[(4-methyl-phen-yl)sulfon-yl]piperazine.

In the title compound, C18H20Cl2N2O2S, the piperazine ring adopts a chair conformation. The dihedral angle between the sulfonyl-bound benzene ring and the best-fit plane through the six non-H atoms of the piperazine ring is 72.22 (12)°; those between the di-chloro-benzene ring and the sulfonyl and piperazine rings are 2.44 (13) and 74.16 (2)°, respectively. In the crystal, mol-ecules are connected through weak C-H⋯O inter-actions into a hexa-meric unit generating a R 6 (6)(60) motif in the ab plane. The mol-ecules are also connected into C(4) chains through weak C-H⋯N inter-actions. The solvent used to grow the crystal was a mixture of di-chloro-methane and methanol, but the resulting electron density was uninter-pretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009 ▶). Acta Cryst. D65, 148-155]. The formula mass and unit-cell characteristics do not take into account the disordered solvent.

Related literature

For similar structures, see: Sreenivasa et al. (2013a ▶,b ▶).

Experimental

Crystal data

C18H20Cl2N2O2S

M = 399.32

Trigonal,

a = 28.2896 (5) Å

c = 13.3041 (3) Å

V = 9220.8 (3) Å3

Z = 18

Mo Kα radiation

μ = 0.43 mm−1

T = 296 K

0.31 × 0.23 × 0.19 mm

Data collection

Bruker APEXII diffractometer

15194 measured reflections

3596 independent reflections

2637 reflections with I > 2σ(I)

R int = 0.033

3608 standard reflections every 22 reflections intensity decay: 1.0%

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 0.95

3596 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301012X/tk5213sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301012X/tk5213Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301012X/tk5213Isup3.cml

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

C18H20Cl2N2O2S	Dx = 1.294 Mg m−3
Mr = 399.32	Melting point: 423 K
Trigonal, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	Cell parameters from 2637 reflections
a = 28.2896 (5) Å	θ = 2.5–25°
c = 13.3041 (3) Å	µ = 0.43 mm−1
V = 9220.8 (3) Å3	T = 296 K
Z = 18	Prism, colourless
F(000) = 3744	0.31 × 0.23 × 0.19 mm
Prism

Bruker APEXII diffractometer	Rint = 0.033
Radiation source: fine-focus sealed tube	θmax = 25.0°, θmin = 2.5°
Graphite monochromator	h = −31→33
phi and ω scans	k = −29→28
15194 measured reflections	l = −15→15
3596 independent reflections	3608 standard reflections every 22 reflections
2637 reflections with I > 2σ(I)	intensity decay: 1.0%

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.0587P)2 + 6.8101P] where P = (Fo2 + 2Fc2)/3
3596 reflections	(Δ/σ)max = 0.089
227 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.25 e Å−3
0 constraints

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

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 > 2σ(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
C1	0.64880 (8)	0.09435 (8)	0.76974 (16)	0.0464 (5)
O2	0.62445 (6)	−0.00584 (6)	0.79558 (13)	0.0674 (5)
N2	0.44379 (7)	−0.01492 (7)	0.71771 (13)	0.0488 (4)
C2	0.65949 (9)	0.14258 (9)	0.81461 (18)	0.0567 (6)
H2	0.6452	0.1423	0.8777	0.068*
N1	0.54532 (7)	0.00797 (7)	0.79761 (12)	0.0458 (4)
C3	0.69137 (10)	0.19115 (10)	0.7653 (2)	0.0654 (7)
H3	0.6984	0.2236	0.7959	0.079*
C4	0.71321 (9)	0.19286 (10)	0.67143 (19)	0.0595 (6)
C5	0.70225 (9)	0.14399 (11)	0.62852 (19)	0.0624 (6)
H5	0.7168	0.1442	0.5657	0.075*
C6	0.67040 (9)	0.09499 (10)	0.67628 (17)	0.0563 (6)
H6	0.6634	0.0625	0.6459	0.068*
O1	0.61109 (6)	0.04263 (7)	0.93700 (12)	0.0678 (5)
C7	0.74895 (12)	0.24614 (12)	0.6180 (2)	0.0928 (9)
H7A	0.7857	0.2527	0.6149	0.139*
H7B	0.7485	0.2753	0.6541	0.139*
H7C	0.7355	0.2443	0.5511	0.139*
C8	0.51725 (8)	0.03596 (9)	0.83632 (18)	0.0530 (6)
H8A	0.5293	0.0698	0.8001	0.064*
H8B	0.5258	0.0445	0.9069	0.064*
C9	0.45666 (9)	−0.00078 (9)	0.82310 (16)	0.0531 (6)
H9A	0.4444	−0.0337	0.8624	0.064*
H9B	0.4377	0.0176	0.8471	0.064*
C10	0.47094 (8)	−0.04358 (9)	0.68121 (17)	0.0522 (5)
H10A	0.4615	−0.0535	0.6113	0.063*
H10B	0.4588	−0.0769	0.7196	0.063*
C11	0.53211 (8)	−0.00766 (9)	0.69135 (16)	0.0538 (6)
H11A	0.5502	−0.0272	0.6688	0.065*
H11B	0.5447	0.0247	0.6501	0.065*
C12	0.38530 (9)	−0.04161 (9)	0.69488 (18)	0.0571 (6)
H12A	0.3804	−0.0505	0.6239	0.068*
H12B	0.3731	−0.0156	0.7069	0.068*
C13	0.34892 (8)	−0.09302 (9)	0.75381 (16)	0.0475 (5)
C14	0.33447 (8)	−0.14556 (9)	0.72265 (16)	0.0492 (5)
C15	0.30393 (8)	−0.19090 (9)	0.78093 (17)	0.0545 (6)
H15	0.2957	−0.2253	0.7586	0.065*
C16	0.28575 (9)	−0.18448 (9)	0.87298 (17)	0.0556 (6)
C17	0.29689 (9)	−0.13381 (10)	0.90606 (18)	0.0600 (6)
H17	0.2837	−0.1298	0.9676	0.072*
C18	0.32797 (9)	−0.08920 (10)	0.84600 (18)	0.0565 (6)
H18	0.3353	−0.0550	0.8681	0.068*
S1	0.60861 (2)	0.03176 (2)	0.83193 (4)	0.05200 (18)
Cl1	0.35347 (3)	−0.15637 (3)	0.60399 (5)	0.0748 (2)
Cl2	0.24812 (3)	−0.24131 (3)	0.94814 (6)	0.0875 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0379 (11)	0.0542 (13)	0.0499 (12)	0.0250 (10)	−0.0040 (9)	−0.0026 (10)
O2	0.0607 (10)	0.0627 (10)	0.0950 (13)	0.0431 (9)	−0.0010 (9)	0.0009 (9)
N2	0.0427 (10)	0.0504 (10)	0.0573 (11)	0.0264 (9)	−0.0001 (8)	0.0044 (8)
C2	0.0525 (14)	0.0616 (15)	0.0552 (14)	0.0278 (12)	0.0022 (11)	−0.0055 (12)
N1	0.0436 (10)	0.0480 (10)	0.0497 (10)	0.0258 (8)	−0.0012 (8)	−0.0079 (8)
C3	0.0589 (15)	0.0552 (15)	0.0773 (18)	0.0248 (12)	−0.0085 (13)	−0.0102 (13)
C4	0.0424 (13)	0.0638 (16)	0.0652 (16)	0.0213 (12)	−0.0084 (11)	0.0070 (12)
C5	0.0506 (14)	0.0795 (18)	0.0567 (15)	0.0321 (13)	0.0024 (11)	0.0042 (13)
C6	0.0487 (13)	0.0640 (15)	0.0590 (14)	0.0303 (12)	−0.0012 (11)	−0.0053 (12)
O1	0.0661 (11)	0.0780 (11)	0.0511 (10)	0.0297 (9)	−0.0086 (8)	0.0039 (8)
C7	0.080 (2)	0.078 (2)	0.096 (2)	0.0213 (16)	−0.0027 (17)	0.0193 (17)
C8	0.0502 (13)	0.0524 (13)	0.0600 (14)	0.0282 (11)	0.0020 (10)	−0.0105 (10)
C9	0.0504 (13)	0.0571 (14)	0.0604 (14)	0.0334 (11)	0.0053 (11)	−0.0067 (11)
C10	0.0494 (13)	0.0582 (13)	0.0500 (13)	0.0278 (11)	−0.0022 (10)	−0.0078 (10)
C11	0.0476 (13)	0.0632 (14)	0.0524 (13)	0.0290 (11)	0.0029 (10)	−0.0101 (11)
C12	0.0515 (13)	0.0636 (15)	0.0633 (15)	0.0341 (12)	−0.0051 (11)	0.0081 (11)
C13	0.0352 (11)	0.0572 (13)	0.0537 (13)	0.0259 (10)	−0.0056 (9)	−0.0021 (10)
C14	0.0367 (11)	0.0631 (14)	0.0469 (12)	0.0242 (11)	−0.0057 (9)	−0.0107 (10)
C15	0.0463 (12)	0.0504 (13)	0.0595 (14)	0.0186 (11)	−0.0053 (10)	−0.0138 (11)
C16	0.0415 (12)	0.0544 (14)	0.0569 (14)	0.0133 (11)	−0.0004 (10)	−0.0044 (11)
C17	0.0506 (13)	0.0647 (15)	0.0569 (14)	0.0230 (12)	0.0089 (11)	−0.0115 (12)
C18	0.0464 (13)	0.0557 (14)	0.0701 (16)	0.0276 (11)	0.0028 (11)	−0.0116 (12)
S1	0.0478 (3)	0.0554 (4)	0.0567 (4)	0.0288 (3)	−0.0042 (2)	0.0013 (3)
Cl1	0.0692 (4)	0.0910 (5)	0.0524 (4)	0.0312 (4)	0.0014 (3)	−0.0202 (3)
Cl2	0.0864 (5)	0.0670 (4)	0.0774 (5)	0.0146 (4)	0.0190 (4)	0.0064 (3)

C1—C2	1.377 (3)	C8—H8A	0.9700
C1—C6	1.382 (3)	C8—H8B	0.9700
C1—S1	1.760 (2)	C9—H9A	0.9700
O2—S1	1.4294 (16)	C9—H9B	0.9700
N2—C9	1.454 (3)	C10—C11	1.512 (3)
N2—C10	1.451 (3)	C10—H10A	0.9700
N2—C12	1.467 (3)	C10—H10B	0.9700
C2—C3	1.375 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
N1—C8	1.467 (2)	C12—C13	1.514 (3)
N1—C11	1.473 (3)	C12—H12A	0.9700
N1—S1	1.6317 (17)	C12—H12B	0.9700
C3—C4	1.384 (3)	C13—C18	1.390 (3)
C3—H3	0.9300	C13—C14	1.393 (3)
C4—C5	1.380 (3)	C14—C15	1.373 (3)
C4—C7	1.508 (3)	C14—Cl1	1.743 (2)
C5—C6	1.374 (3)	C15—C16	1.375 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—H6	0.9300	C16—C17	1.377 (3)
O1—S1	1.4255 (17)	C16—Cl2	1.734 (2)
C7—H7A	0.9600	C17—C18	1.376 (3)
C7—H7B	0.9600	C17—H17	0.9300
C7—H7C	0.9600	C18—H18	0.9300
C8—C9	1.506 (3)
C2—C1—C6	120.0 (2)	N2—C10—C11	110.00 (17)
C2—C1—S1	120.28 (17)	N2—C10—H10A	109.7
C6—C1—S1	119.69 (17)	C11—C10—H10A	109.7
C9—N2—C10	110.30 (16)	N2—C10—H10B	109.7
C9—N2—C12	113.84 (17)	C11—C10—H10B	109.7
C10—N2—C12	114.78 (17)	H10A—C10—H10B	108.2
C3—C2—C1	119.5 (2)	N1—C11—C10	108.70 (17)
C3—C2—H2	120.2	N1—C11—H11A	109.9
C1—C2—H2	120.2	C10—C11—H11A	109.9
C8—N1—C11	112.00 (16)	N1—C11—H11B	110.0
C8—N1—S1	117.23 (13)	C10—C11—H11B	110.0
C11—N1—S1	116.99 (13)	H11A—C11—H11B	108.3
C2—C3—C4	121.6 (2)	N2—C12—C13	115.93 (17)
C2—C3—H3	119.2	N2—C12—H12A	108.3
C4—C3—H3	119.2	C13—C12—H12A	108.3
C5—C4—C3	117.7 (2)	N2—C12—H12B	108.3
C5—C4—C7	120.6 (2)	C13—C12—H12B	108.3
C3—C4—C7	121.7 (3)	H12A—C12—H12B	107.4
C6—C5—C4	121.7 (2)	C18—C13—C14	115.9 (2)
C6—C5—H5	119.2	C18—C13—C12	119.6 (2)
C4—C5—H5	119.2	C14—C13—C12	124.5 (2)
C5—C6—C1	119.5 (2)	C15—C14—C13	122.7 (2)
C5—C6—H6	120.3	C15—C14—Cl1	116.92 (17)
C1—C6—H6	120.3	C13—C14—Cl1	120.33 (17)
C4—C7—H7A	109.5	C14—C15—C16	118.8 (2)
C4—C7—H7B	109.5	C14—C15—H15	120.6
H7A—C7—H7B	109.5	C16—C15—H15	120.6
C4—C7—H7C	109.5	C15—C16—C17	121.1 (2)
H7A—C7—H7C	109.5	C15—C16—Cl2	119.20 (18)
H7B—C7—H7C	109.5	C17—C16—Cl2	119.73 (18)
N1—C8—C9	108.85 (16)	C18—C17—C16	118.5 (2)
N1—C8—H8A	109.9	C18—C17—H17	120.7
C9—C8—H8A	109.9	C16—C17—H17	120.7
N1—C8—H8B	109.9	C17—C18—C13	122.9 (2)
C9—C8—H8B	109.9	C17—C18—H18	118.6
H8A—C8—H8B	108.3	C13—C18—H18	118.6
N2—C9—C8	110.16 (17)	O1—S1—O2	119.49 (10)
N2—C9—H9A	109.6	O1—S1—N1	106.79 (9)
C8—C9—H9A	109.6	O2—S1—N1	106.62 (9)
N2—C9—H9B	109.6	O1—S1—C1	107.86 (10)
C8—C9—H9B	109.6	O2—S1—C1	107.72 (10)
H9A—C9—H9B	108.1	N1—S1—C1	107.89 (9)
C6—C1—C2—C3	0.5 (3)	C12—C13—C14—C15	176.15 (19)
S1—C1—C2—C3	179.42 (17)	C18—C13—C14—Cl1	174.77 (15)
C1—C2—C3—C4	−0.1 (3)	C12—C13—C14—Cl1	−5.6 (3)
C2—C3—C4—C5	−0.4 (3)	C13—C14—C15—C16	1.5 (3)
C2—C3—C4—C7	−179.0 (2)	Cl1—C14—C15—C16	−176.77 (17)
C3—C4—C5—C6	0.6 (3)	C14—C15—C16—C17	1.2 (3)
C7—C4—C5—C6	179.1 (2)	C14—C15—C16—Cl2	−178.92 (16)
C4—C5—C6—C1	−0.2 (3)	C15—C16—C17—C18	−1.7 (4)
C2—C1—C6—C5	−0.3 (3)	Cl2—C16—C17—C18	178.44 (18)
S1—C1—C6—C5	−179.28 (17)	C16—C17—C18—C13	−0.5 (3)
C11—N1—C8—C9	57.6 (2)	C14—C13—C18—C17	2.9 (3)
S1—N1—C8—C9	−163.12 (15)	C12—C13—C18—C17	−176.7 (2)
C10—N2—C9—C8	60.6 (2)	C8—N1—S1—O1	44.09 (18)
C12—N2—C9—C8	−168.74 (17)	C11—N1—S1—O1	−178.60 (15)
N1—C8—C9—N2	−58.1 (2)	C8—N1—S1—O2	172.90 (15)
C9—N2—C10—C11	−60.5 (2)	C11—N1—S1—O2	−49.80 (17)
C12—N2—C10—C11	169.35 (18)	C8—N1—S1—C1	−71.63 (17)
C8—N1—C11—C10	−57.5 (2)	C11—N1—S1—C1	65.67 (17)
S1—N1—C11—C10	163.11 (15)	C2—C1—S1—O1	−23.1 (2)
N2—C10—C11—N1	57.9 (2)	C6—C1—S1—O1	155.79 (17)
C9—N2—C12—C13	−56.4 (2)	C2—C1—S1—O2	−153.37 (17)
C10—N2—C12—C13	72.1 (2)	C6—C1—S1—O2	25.6 (2)
N2—C12—C13—C18	88.3 (2)	C2—C1—S1—N1	91.89 (18)
N2—C12—C13—C14	−91.3 (3)	C6—C1—S1—N1	−89.19 (18)
C18—C13—C14—C15	−3.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2i	0.93	2.70	3.575 (3)	157
C17—H17···N2ii	0.93	2.70	3.485 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2i	0.93	2.70	3.575 (3)	157
C17—H17⋯N2ii	0.93	2.70	3.485 (3)	143

Symmetry codes: (i) ; (ii) .