1-(4-Bromo-phen-yl)-2-ethyl-sulfinyl-2-(phenyl-selan-yl)ethanone monohydrate.

In the title hydrate, C(16)H(15)BrO(2)SSe·H(2)O, the sulfinyl O atom lies on the opposite side of the mol-ecule to the Se and carbonyl O atoms. The benzene rings form a dihedral angle of 51.66 (17)° and are splayed with respect to each other. The observed conformation allows the water mol-ecules to bridge sulfinyl O atoms via O-H⋯O hydrogen bonds, generating a linear supra-molecular chain along the b axis; the chain is further stabilized by C-H⋯O contacts. The chains are held in place in the crystal structure by C⋯H⋯π and C-Br⋯π inter-actions.

Related literature

For background to β,β-bis-substituted-carbonyl compounds, see: Reis et al. (2006 ▶). For related structures, see: Olivato et al. (2004 ▶); Zukerman-Schpector et al. (2009 ▶, 2010 ▶). For details of the synthetic protocols, see: Long (1946 ▶); Leonard & Johnson (1962 ▶); Zoretic & Soja (1976 ▶).

Experimental

Crystal data

C16H15BrO2SSe·H2O

M = 448.23

Monoclinic,

a = 14.6942 (2) Å

b = 6.1103 (1) Å

c = 21.5717 (4) Å

β = 113.714 (1)°

V = 1773.30 (5) Å3

Z = 4

Mo Kα radiation

μ = 4.50 mm−1

T = 290 K

0.36 × 0.19 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.291, T max = 0.734

32063 measured reflections

3734 independent reflections

3177 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.095

S = 1.03

3734 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.55 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012712/hg5022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012712/hg5022Isup2.hkl

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

C16H15BrO2SSe·H2O	F(000) = 888
Mr = 448.23	Dx = 1.679 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 23524 reflections
a = 14.6942 (2) Å	θ = 2.6–26.7°
b = 6.1103 (1) Å	µ = 4.50 mm−1
c = 21.5717 (4) Å	T = 290 K
β = 113.714 (1)°	Plate, colourless
V = 1773.30 (5) Å3	0.36 × 0.19 × 0.16 mm
Z = 4

Nonius KappaCCD diffractometer	3734 independent reflections
Radiation source: sealed tube	3177 reflections with I > 2σ(I)
graphite	Rint = 0.076
CCD rotation images scans	θmax = 26.7°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→18
Tmin = 0.291, Tmax = 0.734	k = −7→7
32063 measured reflections	l = −27→25

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0428P)2 + 1.5141P] where P = (Fo2 + 2Fc2)/3
3734 reflections	(Δ/σ)max < 0.001
200 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.55 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
C1	0.27316 (19)	0.2209 (5)	0.25810 (14)	0.0424 (6)
C2	0.36493 (19)	0.1572 (5)	0.32017 (13)	0.0419 (6)
H2	0.4114	0.0804	0.3055	0.050*
C3	0.5393 (2)	0.2846 (6)	0.42271 (17)	0.0593 (8)
H3A	0.5269	0.1896	0.4545	0.071*
H3B	0.5683	0.1973	0.3977	0.071*
C4	0.6102 (3)	0.4646 (8)	0.4605 (2)	0.0811 (12)
H4A	0.5806	0.5522	0.4844	0.122*
H4B	0.6243	0.5547	0.4290	0.122*
H4C	0.6709	0.4014	0.4922	0.122*
C5	0.23970 (19)	0.0756 (5)	0.19795 (14)	0.0409 (6)
C6	0.1669 (2)	0.1548 (5)	0.13798 (15)	0.0488 (6)
H6	0.1396	0.2925	0.1373	0.059*
C7	0.1349 (2)	0.0315 (5)	0.07957 (16)	0.0544 (7)
H7	0.0868	0.0854	0.0395	0.065*
C8	0.1756 (2)	−0.1734 (5)	0.08164 (15)	0.0503 (7)
C9	0.2473 (2)	−0.2565 (5)	0.14005 (16)	0.0506 (7)
H9	0.2736	−0.3952	0.1405	0.061*
C10	0.2796 (2)	−0.1304 (5)	0.19819 (15)	0.0470 (6)
H10	0.3287	−0.1843	0.2379	0.056*
C11	0.1967 (2)	0.0520 (5)	0.36178 (14)	0.0468 (6)
C12	0.1754 (3)	0.2435 (6)	0.38661 (18)	0.0612 (8)
H12	0.2261	0.3392	0.4116	0.073*
C13	0.0772 (3)	0.2921 (7)	0.3739 (2)	0.0709 (10)
H13	0.0618	0.4222	0.3900	0.085*
C14	0.0026 (3)	0.1487 (8)	0.33776 (19)	0.0722 (10)
H14	−0.0631	0.1809	0.3298	0.087*
C15	0.0248 (3)	−0.0399 (8)	0.3137 (2)	0.0713 (10)
H15	−0.0259	−0.1368	0.2894	0.086*
C16	0.1217 (2)	−0.0899 (6)	0.32472 (17)	0.0577 (8)
H16	0.1362	−0.2181	0.3073	0.069*
O1	0.22999 (15)	0.3895 (3)	0.25913 (11)	0.0532 (5)
O2	0.45208 (18)	0.5313 (4)	0.31552 (12)	0.0643 (6)
O1W	0.4391 (2)	0.4022 (4)	0.18722 (14)	0.0729 (7)
H1W	0.4651	0.2794	0.1849	0.088*
H2W	0.4411	0.4158	0.2263	0.088*
S	0.42388 (5)	0.40496 (12)	0.36491 (4)	0.04610 (18)
Se	0.33094 (2)	−0.03515 (6)	0.380920 (17)	0.05674 (12)
Br	0.13073 (3)	−0.34569 (7)	0.001765 (19)	0.07905 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0385 (13)	0.0460 (15)	0.0428 (15)	−0.0001 (11)	0.0165 (11)	0.0043 (11)
C2	0.0366 (13)	0.0488 (15)	0.0393 (14)	0.0033 (11)	0.0143 (11)	−0.0005 (11)
C3	0.0458 (16)	0.077 (2)	0.0477 (17)	−0.0005 (15)	0.0116 (13)	−0.0088 (16)
C4	0.054 (2)	0.114 (3)	0.067 (2)	−0.015 (2)	0.0156 (18)	−0.030 (2)
C5	0.0351 (12)	0.0465 (14)	0.0402 (14)	−0.0005 (11)	0.0144 (11)	0.0018 (11)
C6	0.0438 (14)	0.0497 (16)	0.0474 (16)	0.0058 (12)	0.0127 (12)	0.0029 (12)
C7	0.0494 (16)	0.0604 (18)	0.0426 (16)	0.0017 (14)	0.0073 (13)	0.0028 (13)
C8	0.0491 (15)	0.0589 (18)	0.0440 (15)	−0.0071 (13)	0.0199 (13)	−0.0048 (13)
C9	0.0498 (15)	0.0490 (16)	0.0527 (17)	0.0008 (13)	0.0203 (13)	−0.0028 (13)
C10	0.0410 (14)	0.0505 (16)	0.0442 (15)	0.0017 (12)	0.0116 (12)	0.0036 (12)
C11	0.0484 (15)	0.0545 (16)	0.0403 (15)	−0.0053 (12)	0.0207 (12)	0.0044 (12)
C12	0.0638 (19)	0.062 (2)	0.0597 (19)	−0.0092 (16)	0.0271 (16)	−0.0088 (16)
C13	0.078 (2)	0.077 (2)	0.070 (2)	0.0102 (19)	0.043 (2)	−0.0010 (19)
C14	0.0531 (19)	0.109 (3)	0.061 (2)	0.003 (2)	0.0298 (17)	0.014 (2)
C15	0.0543 (19)	0.099 (3)	0.062 (2)	−0.0205 (19)	0.0248 (17)	−0.007 (2)
C16	0.0591 (18)	0.0643 (19)	0.0530 (18)	−0.0161 (15)	0.0260 (15)	−0.0090 (15)
O1	0.0507 (11)	0.0509 (11)	0.0526 (12)	0.0099 (9)	0.0149 (9)	−0.0012 (9)
O2	0.0661 (14)	0.0659 (14)	0.0611 (14)	−0.0174 (11)	0.0258 (12)	0.0026 (11)
O1W	0.0846 (17)	0.0675 (15)	0.0766 (17)	0.0192 (13)	0.0428 (14)	0.0114 (13)
S	0.0449 (4)	0.0504 (4)	0.0427 (4)	−0.0023 (3)	0.0172 (3)	−0.0049 (3)
Se	0.05056 (19)	0.0595 (2)	0.0579 (2)	0.00582 (13)	0.01947 (15)	0.01869 (14)
Br	0.0929 (3)	0.0816 (3)	0.0526 (2)	−0.0047 (2)	0.01875 (19)	−0.02037 (18)

C1—O1	1.215 (3)	C8—Br	1.897 (3)
C1—C5	1.483 (4)	C9—C10	1.383 (4)
C1—C2	1.520 (4)	C9—H9	0.9300
C2—S	1.817 (3)	C10—H10	0.9300
C2—Se	1.969 (3)	C11—C12	1.375 (5)
C2—H2	0.9800	C11—C16	1.377 (4)
C3—C4	1.509 (5)	C11—Se	1.920 (3)
C3—S	1.809 (3)	C12—C13	1.388 (5)
C3—H3A	0.9700	C12—H12	0.9300
C3—H3B	0.9700	C13—C14	1.375 (6)
C4—H4A	0.9600	C13—H13	0.9300
C4—H4B	0.9600	C14—C15	1.357 (6)
C4—H4C	0.9600	C14—H14	0.9300
C5—C10	1.388 (4)	C15—C16	1.380 (5)
C5—C6	1.392 (4)	C15—H15	0.9300
C6—C7	1.378 (4)	C16—H16	0.9300
C6—H6	0.9300	O2—S	1.503 (2)
C7—C8	1.380 (4)	O1W—H1W	0.8525
C7—H7	0.9300	O1W—H2W	0.8362
C8—C9	1.374 (4)
O1—C1—C5	122.1 (2)	C9—C8—Br	119.1 (2)
O1—C1—C2	119.1 (3)	C7—C8—Br	119.1 (2)
C5—C1—C2	118.8 (2)	C8—C9—C10	118.8 (3)
C1—C2—S	108.62 (19)	C8—C9—H9	120.6
C1—C2—Se	111.50 (17)	C10—C9—H9	120.6
S—C2—Se	109.77 (14)	C9—C10—C5	120.8 (3)
C1—C2—H2	109.0	C9—C10—H10	119.6
S—C2—H2	109.0	C5—C10—H10	119.6
Se—C2—H2	109.0	C12—C11—C16	120.4 (3)
C4—C3—S	109.2 (3)	C12—C11—Se	121.9 (2)
C4—C3—H3A	109.8	C16—C11—Se	117.6 (2)
S—C3—H3A	109.8	C11—C12—C13	119.2 (3)
C4—C3—H3B	109.8	C11—C12—H12	120.4
S—C3—H3B	109.8	C13—C12—H12	120.4
H3A—C3—H3B	108.3	C14—C13—C12	120.2 (4)
C3—C4—H4A	109.5	C14—C13—H13	119.9
C3—C4—H4B	109.5	C12—C13—H13	119.9
H4A—C4—H4B	109.5	C15—C14—C13	119.9 (3)
C3—C4—H4C	109.5	C15—C14—H14	120.0
H4A—C4—H4C	109.5	C13—C14—H14	120.0
H4B—C4—H4C	109.5	C14—C15—C16	120.8 (3)
C10—C5—C6	118.9 (3)	C14—C15—H15	119.6
C10—C5—C1	123.3 (2)	C16—C15—H15	119.6
C6—C5—C1	117.7 (2)	C11—C16—C15	119.4 (3)
C7—C6—C5	120.8 (3)	C11—C16—H16	120.3
C7—C6—H6	119.6	C15—C16—H16	120.3
C5—C6—H6	119.6	H1W—O1W—H2W	108.1
C6—C7—C8	118.8 (3)	O2—S—C3	104.37 (15)
C6—C7—H7	120.6	O2—S—C2	105.07 (13)
C8—C7—H7	120.6	C3—S—C2	98.16 (14)
C9—C8—C7	121.8 (3)	C11—Se—C2	101.82 (11)
O1—C1—C2—S	−28.1 (3)	C16—C11—C12—C13	0.1 (5)
C5—C1—C2—S	151.4 (2)	Se—C11—C12—C13	−176.7 (3)
O1—C1—C2—Se	93.0 (3)	C11—C12—C13—C14	0.9 (5)
C5—C1—C2—Se	−87.5 (2)	C12—C13—C14—C15	−0.8 (6)
O1—C1—C5—C10	−171.6 (3)	C13—C14—C15—C16	−0.3 (6)
C2—C1—C5—C10	8.9 (4)	C12—C11—C16—C15	−1.1 (5)
O1—C1—C5—C6	10.6 (4)	Se—C11—C16—C15	175.8 (3)
C2—C1—C5—C6	−168.9 (2)	C14—C15—C16—C11	1.3 (6)
C10—C5—C6—C7	−0.2 (4)	C4—C3—S—O2	64.1 (3)
C1—C5—C6—C7	177.7 (3)	C4—C3—S—C2	172.0 (3)
C5—C6—C7—C8	0.7 (5)	C1—C2—S—O2	−61.3 (2)
C6—C7—C8—C9	−0.5 (5)	Se—C2—S—O2	176.53 (14)
C6—C7—C8—Br	179.2 (2)	C1—C2—S—C3	−168.7 (2)
C7—C8—C9—C10	−0.2 (5)	Se—C2—S—C3	69.18 (16)
Br—C8—C9—C10	−179.9 (2)	C12—C11—Se—C2	−76.2 (3)
C8—C9—C10—C5	0.7 (4)	C16—C11—Se—C2	106.9 (2)
C6—C5—C10—C9	−0.5 (4)	C1—C2—Se—C11	−27.7 (2)
C1—C5—C10—C9	−178.3 (3)	S—C2—Se—C11	92.67 (15)

Cg1 and Cg2 are the centroids of the C5–C10 and C11–C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w···O2i	0.85	1.95	2.788 (4)	169
O1w—H2w···O2	0.84	1.99	2.810 (4)	165
C2—H2···O1wi	0.98	2.40	3.334 (4)	159
C3—H3b···O1wi	0.97	2.54	3.434 (4)	153
C9—H9···O1wii	0.93	2.55	3.320 (4)	141
C10—H10···O2ii	0.93	2.58	3.456 (4)	157
C14—H14···Cg1iii	0.93	2.96	3.793 (5)	149
C8—Br···Cg2iv	1.897 (3)	3.4921 (16)	5.349 (3)	165.34 (10)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C5–C10 and C11–C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w⋯O2i	0.85	1.95	2.788 (4)	169
O1w—H2w⋯O2	0.84	1.99	2.810 (4)	165
C2—H2⋯O1wi	0.98	2.40	3.334 (4)	159
C3—H3b⋯O1wi	0.97	2.54	3.434 (4)	153
C9—H9⋯O1wii	0.93	2.55	3.320 (4)	141
C10—H10⋯O2ii	0.93	2.58	3.456 (4)	157
C14—H14⋯Cg1iii	0.93	2.96	3.793 (5)	149
C8—Br⋯Cg2iv	1.90 (1)	3.49 (1)	5.349 (3)	165 (1)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .