Ethyl 4-(phenyl-sulfon-yl)piperazine-1-carboxyl-ate.

In the title compound, C(13)H(18)N(2)O(4)S, the piperazine ring adopts a chair conformation. The dihedral angle between the least-squares planes through the piperazine and benzene rings is 73.23 (10)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C-H⋯π inter-actions.

Related literature

For the biological activity of piperazine derivatives, see: Emami et al. (2006 ▶); Foroumadi et al. (2007 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C13H18N2O4S

M = 298.35

Monoclinic,

a = 6.1433 (5) Å

b = 20.5966 (17) Å

c = 12.5626 (8) Å

β = 114.026 (3)°

V = 1451.84 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 296 K

0.58 × 0.38 × 0.17 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.875, T max = 0.961

16507 measured reflections

4255 independent reflections

3400 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.158

S = 1.04

4255 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.60 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033162/tk2781sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033162/tk2781Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033162/tk2781Isup3.cml

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

C13H18N2O4S	F(000) = 632
Mr = 298.35	Dx = 1.365 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5957 reflections
a = 6.1433 (5) Å	θ = 2.7–29.7°
b = 20.5966 (17) Å	µ = 0.24 mm−1
c = 12.5626 (8) Å	T = 296 K
β = 114.026 (3)°	Block, yellow
V = 1451.84 (19) Å3	0.58 × 0.38 × 0.17 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	4255 independent reflections
Radiation source: fine-focus sealed tube	3400 reflections with I > 2σ(I)
graphite	Rint = 0.023
φ and ω scans	θmax = 30.1°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
Tmin = 0.875, Tmax = 0.961	k = −29→24
16507 measured reflections	l = −17→17

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0887P)2 + 0.3986P] where P = (Fo2 + 2Fc2)/3
4255 reflections	(Δ/σ)max = 0.001
182 parameters	Δρmax = 0.60 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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
S1	0.36299 (7)	−0.120155 (19)	0.94030 (3)	0.03858 (14)
O1	0.3060 (3)	−0.12052 (6)	1.04000 (10)	0.0517 (3)
O2	0.6074 (2)	−0.12032 (7)	0.95617 (12)	0.0547 (3)
O3	−0.1090 (3)	0.07756 (8)	0.52229 (12)	0.0659 (4)
O4	−0.3840 (2)	0.07205 (8)	0.59831 (12)	0.0605 (4)
N1	0.2424 (2)	−0.05482 (6)	0.86538 (10)	0.0346 (3)
N2	−0.0094 (2)	0.04239 (7)	0.70682 (12)	0.0412 (3)
C1	0.0247 (4)	−0.21553 (9)	0.86231 (18)	0.0544 (4)
H1A	−0.0323	−0.1999	0.9156	0.065*
C2	−0.0839 (4)	−0.26783 (11)	0.7902 (2)	0.0749 (7)
H2A	−0.2149	−0.2877	0.7957	0.090*
C3	−0.0001 (5)	−0.29053 (11)	0.7108 (2)	0.0813 (8)
H3A	−0.0749	−0.3255	0.6630	0.098*
C4	0.1924 (5)	−0.26197 (12)	0.7021 (2)	0.0785 (7)
H4A	0.2477	−0.2776	0.6482	0.094*
C5	0.3063 (4)	−0.20992 (11)	0.77261 (18)	0.0595 (5)
H5A	0.4375	−0.1905	0.7666	0.071*
C6	0.2208 (3)	−0.18732 (8)	0.85247 (14)	0.0421 (3)
C7	−0.0086 (3)	−0.04191 (8)	0.84341 (13)	0.0376 (3)
H7A	−0.0340	−0.0501	0.9135	0.045*
H7B	−0.1126	−0.0704	0.7824	0.045*
C8	−0.0652 (3)	0.02844 (8)	0.80650 (14)	0.0406 (3)
H8A	−0.2328	0.0367	0.7862	0.049*
H8B	0.0271	0.0567	0.8708	0.049*
C9	0.2364 (3)	0.02842 (9)	0.72652 (16)	0.0472 (4)
H9A	0.3431	0.0565	0.7873	0.057*
H9B	0.2594	0.0367	0.6558	0.057*
C10	0.2931 (3)	−0.04207 (9)	0.76225 (14)	0.0423 (3)
H10A	0.1969	−0.0703	0.6987	0.051*
H10B	0.4597	−0.0508	0.7804	0.051*
C11	−0.1625 (3)	0.06530 (8)	0.60275 (14)	0.0436 (4)
C12	−0.5669 (4)	0.09306 (12)	0.48616 (18)	0.0637 (5)
H12A	−0.5300	0.0763	0.4233	0.076*
H12C	−0.7206	0.0759	0.4769	0.076*
C13	−0.5775 (7)	0.16308 (16)	0.4804 (3)	0.1174 (13)
H13A	−0.6971	0.1763	0.4064	0.176*
H13B	−0.4254	0.1799	0.4891	0.176*
H13C	−0.6170	0.1795	0.5418	0.176*

	U11	U22	U33	U12	U13	U23
S1	0.0397 (2)	0.0421 (2)	0.0286 (2)	0.00210 (13)	0.00853 (15)	0.00111 (13)
O1	0.0710 (9)	0.0526 (7)	0.0297 (6)	0.0009 (6)	0.0187 (6)	0.0025 (5)
O2	0.0368 (6)	0.0628 (8)	0.0521 (8)	0.0056 (5)	0.0053 (5)	0.0070 (6)
O3	0.0668 (9)	0.0926 (11)	0.0443 (7)	0.0176 (8)	0.0288 (6)	0.0217 (7)
O4	0.0449 (7)	0.0863 (10)	0.0481 (7)	0.0147 (6)	0.0167 (6)	0.0204 (7)
N1	0.0342 (6)	0.0394 (6)	0.0305 (6)	0.0018 (5)	0.0136 (5)	0.0023 (5)
N2	0.0382 (6)	0.0502 (7)	0.0376 (6)	0.0057 (5)	0.0179 (5)	0.0107 (6)
C1	0.0568 (10)	0.0465 (9)	0.0550 (10)	−0.0022 (8)	0.0178 (8)	0.0017 (8)
C2	0.0690 (14)	0.0462 (11)	0.0853 (17)	−0.0098 (9)	0.0065 (12)	0.0024 (11)
C3	0.0979 (19)	0.0399 (10)	0.0691 (15)	0.0061 (11)	−0.0039 (13)	−0.0143 (10)
C4	0.1010 (19)	0.0625 (14)	0.0608 (13)	0.0193 (13)	0.0213 (13)	−0.0212 (11)
C5	0.0699 (12)	0.0580 (11)	0.0521 (10)	0.0106 (9)	0.0262 (9)	−0.0092 (9)
C6	0.0470 (8)	0.0366 (8)	0.0374 (7)	0.0065 (6)	0.0119 (6)	0.0000 (6)
C7	0.0366 (7)	0.0439 (8)	0.0364 (7)	0.0003 (6)	0.0192 (6)	0.0037 (6)
C8	0.0435 (7)	0.0449 (8)	0.0373 (7)	0.0074 (6)	0.0205 (6)	0.0040 (6)
C9	0.0376 (7)	0.0587 (10)	0.0494 (9)	0.0020 (7)	0.0220 (7)	0.0164 (8)
C10	0.0380 (7)	0.0556 (9)	0.0386 (8)	0.0075 (6)	0.0210 (6)	0.0076 (7)
C11	0.0455 (8)	0.0477 (9)	0.0375 (8)	0.0038 (6)	0.0169 (6)	0.0053 (6)
C12	0.0510 (10)	0.0811 (15)	0.0494 (10)	0.0032 (10)	0.0104 (8)	0.0043 (10)
C13	0.131 (3)	0.077 (2)	0.101 (2)	0.0254 (18)	0.003 (2)	0.0136 (17)

S1—O1	1.4312 (13)	C4—H4A	0.9300
S1—O2	1.4320 (14)	C5—C6	1.389 (2)
S1—N1	1.6365 (13)	C5—H5A	0.9300
S1—C6	1.7634 (17)	C7—C8	1.518 (2)
O3—C11	1.210 (2)	C7—H7A	0.9700
O4—C11	1.346 (2)	C7—H7B	0.9700
O4—C12	1.465 (2)	C8—H8A	0.9700
N1—C10	1.4745 (18)	C8—H8B	0.9700
N1—C7	1.4755 (18)	C9—C10	1.518 (2)
N2—C11	1.347 (2)	C9—H9A	0.9700
N2—C8	1.4554 (19)	C9—H9B	0.9700
N2—C9	1.455 (2)	C10—H10A	0.9700
C1—C6	1.387 (3)	C10—H10B	0.9700
C1—C2	1.391 (3)	C12—C13	1.444 (4)
C1—H1A	0.9300	C12—H12A	0.9700
C2—C3	1.377 (4)	C12—H12C	0.9700
C2—H2A	0.9300	C13—H13A	0.9600
C3—C4	1.365 (4)	C13—H13B	0.9600
C3—H3A	0.9300	C13—H13C	0.9600
C4—C5	1.385 (3)
O1—S1—O2	119.62 (9)	C8—C7—H7B	109.9
O1—S1—N1	107.02 (7)	H7A—C7—H7B	108.3
O2—S1—N1	106.60 (7)	N2—C8—C7	110.26 (12)
O1—S1—C6	107.94 (8)	N2—C8—H8A	109.6
O2—S1—C6	108.04 (8)	C7—C8—H8A	109.6
N1—S1—C6	107.00 (7)	N2—C8—H8B	109.6
C11—O4—C12	115.91 (15)	C7—C8—H8B	109.6
C10—N1—C7	112.47 (11)	H8A—C8—H8B	108.1
C10—N1—S1	116.33 (10)	N2—C9—C10	109.69 (13)
C7—N1—S1	116.73 (10)	N2—C9—H9A	109.7
C11—N2—C8	126.01 (13)	C10—C9—H9A	109.7
C11—N2—C9	120.02 (13)	N2—C9—H9B	109.7
C8—N2—C9	113.96 (12)	C10—C9—H9B	109.7
C6—C1—C2	118.1 (2)	H9A—C9—H9B	108.2
C6—C1—H1A	121.0	N1—C10—C9	108.96 (13)
C2—C1—H1A	121.0	N1—C10—H10A	109.9
C3—C2—C1	120.9 (2)	C9—C10—H10A	109.9
C3—C2—H2A	119.6	N1—C10—H10B	109.9
C1—C2—H2A	119.6	C9—C10—H10B	109.9
C4—C3—C2	120.2 (2)	H10A—C10—H10B	108.3
C4—C3—H3A	119.9	O3—C11—O4	123.90 (15)
C2—C3—H3A	119.9	O3—C11—N2	124.31 (16)
C3—C4—C5	120.7 (2)	O4—C11—N2	111.78 (14)
C3—C4—H4A	119.6	C13—C12—O4	110.2 (2)
C5—C4—H4A	119.6	C13—C12—H12A	109.6
C4—C5—C6	118.7 (2)	O4—C12—H12A	109.6
C4—C5—H5A	120.7	C13—C12—H12C	109.6
C6—C5—H5A	120.7	O4—C12—H12C	109.6
C1—C6—C5	121.44 (18)	H12A—C12—H12C	108.1
C1—C6—S1	119.99 (14)	C12—C13—H13A	109.5
C5—C6—S1	118.55 (15)	C12—C13—H13B	109.5
N1—C7—C8	108.73 (12)	H13A—C13—H13B	109.5
N1—C7—H7A	109.9	C12—C13—H13C	109.5
C8—C7—H7A	109.9	H13A—C13—H13C	109.5
N1—C7—H7B	109.9	H13B—C13—H13C	109.5
O1—S1—N1—C10	175.82 (11)	N1—S1—C6—C5	85.65 (15)
O2—S1—N1—C10	46.71 (13)	C10—N1—C7—C8	−58.52 (17)
C6—S1—N1—C10	−68.69 (13)	S1—N1—C7—C8	163.26 (10)
O1—S1—N1—C7	−47.57 (12)	C11—N2—C8—C7	122.68 (18)
O2—S1—N1—C7	−176.67 (11)	C9—N2—C8—C7	−56.43 (18)
C6—S1—N1—C7	67.92 (12)	N1—C7—C8—N2	55.05 (16)
C6—C1—C2—C3	−0.5 (3)	C11—N2—C9—C10	−122.59 (17)
C1—C2—C3—C4	0.2 (4)	C8—N2—C9—C10	56.58 (19)
C2—C3—C4—C5	0.0 (4)	C7—N1—C10—C9	59.10 (17)
C3—C4—C5—C6	0.0 (3)	S1—N1—C10—C9	−162.49 (11)
C2—C1—C6—C5	0.5 (3)	N2—C9—C10—N1	−55.79 (18)
C2—C1—C6—S1	179.12 (15)	C12—O4—C11—O3	2.6 (3)
C4—C5—C6—C1	−0.3 (3)	C12—O4—C11—N2	−176.51 (17)
C4—C5—C6—S1	−178.91 (16)	C8—N2—C11—O3	178.53 (18)
O1—S1—C6—C1	21.89 (16)	C9—N2—C11—O3	−2.4 (3)
O2—S1—C6—C1	152.57 (14)	C8—N2—C11—O4	−2.4 (2)
N1—S1—C6—C1	−92.99 (15)	C9—N2—C11—O4	176.66 (15)
O1—S1—C6—C5	−159.47 (14)	C11—O4—C12—C13	−88.6 (3)
O2—S1—C6—C5	−28.79 (17)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···Cg1i	0.96	2.97	3.900 (4)	165

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Cg1i	0.96	2.97	3.900 (4)	165

Symmetry code: (i) .