Crystal structure of (2E)-1-(1-benzo-furan-2-yl)-3-(2-bromo-phen-yl)prop-2-en-1-one monohydrate.

The title compound, C17H11BrO2·H2O, crystallizes as a monohydrate in the chiral ortho-rhom-bic space group P212121, and has non-linear optical (NLO) properties. The mol-ecule has an E conformation about the C=C bond and is relatively planar with the benzo-furan and bromo-phenyl rings being inclined to one another by 10.60 (14)°. In the crystal, the water mol-ecule is linked to the organic mol-ecule by O-H⋯O hydrogen bonds, forming an R (2) 2(7) ring motif while C-H⋯O hydrogen bonds lead to the formation of helices along the b-axis direction.

Related literature

For background to chalcones and their biological and other properties, see: Choudary et al. (1999 ▸); Jayarama et al. (2013 ▸); Tomazela et al. (2000 ▸); Gu et al. (2008 ▸). For the crystal structure of a similar compound, see: Benmekhbi et al. (2009 ▸).

Experimental

Crystal data

C17H11BrO2·H2O

M = 345.18

Orthorhombic,

a = 4.8614 (4) Å

b = 13.8220 (15) Å

c = 21.755 (2) Å

V = 1461.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.82 mm−1

T = 296 K

0.40 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.399, T max = 0.539

3636 measured reflections

3636 independent reflections

2134 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.102

S = 1.01

3636 reflections

196 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▸), 1497 Friedel pairs

Absolute structure parameter: −0.011 (11)

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S2056989015018897/su5214sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018897/su5214Isup3.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015018897/su5214Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015018897/su5214fig1.tif

A view of the mol­ecular structure of title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989015018897/su5214fig2.tif

A view along the a-axis of the crystal packing of the title compound. The inter­molecular inter­actions are represented by dashed lines (see Table 1).

CCDC reference: 1430039

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H11BrO2·H2O	F(000) = 696
Mr = 345.18	Dx = 1.568 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2499 reflections
a = 4.8614 (4) Å	θ = 4.8–41.6°
b = 13.8220 (15) Å	µ = 2.82 mm−1
c = 21.755 (2) Å	T = 296 K
V = 1461.8 (2) Å3	Block, golden-yellow
Z = 4	0.40 × 0.30 × 0.25 mm

Bruker Kappa APEXII CCD diffractometer	3636 independent reflections
Radiation source: fine-focus sealed tube	2134 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
ω and φ scan	θmax = 28.4°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −6→5
Tmin = 0.399, Tmax = 0.539	k = −18→18
3636 measured reflections	l = −28→29

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0372P)2 + 0.0197P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.001
3636 reflections	Δρmax = 0.42 e Å−3
196 parameters	Δρmin = −0.29 e Å−3
3 restraints	Absolute structure: Flack (1983), 1497 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.011 (11)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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
Br1	1.34723 (10)	0.98219 (3)	0.06738 (2)	0.0902 (2)
O1	0.3289 (4)	0.93267 (17)	0.32535 (10)	0.0513 (5)
O2	0.6697 (5)	0.99535 (19)	0.23842 (13)	0.0720 (7)
C1	0.1694 (7)	0.8801 (2)	0.36525 (14)	0.0463 (8)
C2	−0.0186 (7)	0.9171 (3)	0.40591 (16)	0.0593 (10)
H2	−0.0523	0.9831	0.4093	0.071*
C3	−0.1522 (7)	0.8509 (3)	0.44089 (16)	0.0634 (10)
H3	−0.2812	0.8724	0.4694	0.076*
C4	−0.1034 (7)	0.7519 (3)	0.43576 (17)	0.0607 (9)
H4	−0.2020	0.7091	0.4603	0.073*
C5	0.0860 (7)	0.7169 (3)	0.39547 (16)	0.0587 (10)
H5	0.1185	0.6507	0.3923	0.070*
C6	0.2301 (6)	0.7824 (3)	0.35908 (14)	0.0444 (8)
C7	0.4402 (6)	0.7757 (3)	0.31357 (15)	0.0468 (8)
H7	0.5256	0.7195	0.2997	0.056*
C8	0.4907 (6)	0.8671 (3)	0.29448 (15)	0.0463 (9)
C9	0.6756 (7)	0.9078 (3)	0.24929 (15)	0.0503 (8)
C10	0.8640 (6)	0.8424 (2)	0.21760 (14)	0.0446 (7)
H10	0.8712	0.7779	0.2297	0.054*
C11	1.0223 (6)	0.8713 (3)	0.17288 (16)	0.0480 (8)
H11	1.0081	0.9361	0.1619	0.058*
C12	1.2190 (6)	0.8136 (3)	0.13815 (14)	0.0439 (8)
C13	1.2629 (7)	0.7170 (3)	0.15197 (16)	0.0523 (9)
H13	1.1617	0.6892	0.1837	0.063*
C14	1.4478 (7)	0.6610 (3)	0.12115 (19)	0.0615 (10)
H14	1.4691	0.5961	0.1315	0.074*
C15	1.6028 (7)	0.7008 (3)	0.07476 (17)	0.0603 (10)
H15	1.7313	0.6633	0.0539	0.072*
C16	1.5667 (7)	0.7964 (3)	0.05931 (16)	0.0557 (9)
H16	1.6695	0.8239	0.0278	0.067*
C17	1.3787 (7)	0.8507 (3)	0.09068 (14)	0.0493 (8)
O1S	0.1601 (7)	1.1082 (2)	0.23870 (17)	0.0950 (10)
H1SA	0.179 (11)	1.078 (4)	0.2780 (12)	0.143*
H1SB	0.300 (9)	1.070 (3)	0.220 (2)	0.143*

	U11	U22	U33	U12	U13	U23
Br1	0.1130 (4)	0.0695 (3)	0.0881 (3)	0.0070 (3)	0.0327 (3)	0.0255 (2)
O1	0.0458 (12)	0.0526 (14)	0.0555 (14)	0.0017 (11)	0.0037 (12)	−0.0104 (11)
O2	0.0594 (14)	0.0592 (19)	0.0974 (19)	0.0071 (14)	0.0271 (13)	0.0068 (15)
C1	0.0391 (17)	0.057 (2)	0.0426 (18)	−0.0028 (18)	−0.0028 (16)	−0.0049 (15)
C2	0.0461 (19)	0.079 (3)	0.053 (2)	0.0023 (19)	0.0023 (17)	−0.016 (2)
C3	0.0426 (18)	0.104 (3)	0.044 (2)	−0.003 (2)	0.0102 (19)	−0.009 (2)
C4	0.056 (2)	0.081 (3)	0.0447 (19)	−0.0068 (19)	0.002 (2)	0.008 (2)
C5	0.058 (2)	0.065 (2)	0.054 (2)	0.0003 (19)	−0.0023 (18)	0.0054 (19)
C6	0.0340 (17)	0.058 (2)	0.0408 (17)	0.0013 (15)	−0.0096 (14)	−0.0056 (16)
C7	0.0383 (17)	0.056 (2)	0.0460 (19)	0.0050 (15)	−0.0053 (15)	−0.0044 (17)
C8	0.0323 (16)	0.060 (2)	0.047 (2)	0.0051 (16)	−0.0044 (14)	−0.0082 (18)
C9	0.0368 (17)	0.060 (2)	0.054 (2)	−0.0001 (18)	−0.0042 (16)	−0.0041 (17)
C10	0.0346 (16)	0.052 (2)	0.0469 (18)	−0.0021 (17)	0.0011 (16)	0.0002 (15)
C11	0.0423 (16)	0.055 (2)	0.047 (2)	0.0008 (16)	−0.0021 (16)	0.0048 (16)
C12	0.0302 (16)	0.060 (2)	0.0419 (18)	−0.0028 (15)	−0.0042 (13)	−0.0007 (16)
C13	0.050 (2)	0.056 (2)	0.051 (2)	0.0004 (17)	0.0043 (15)	0.0046 (18)
C14	0.059 (2)	0.057 (2)	0.068 (3)	0.0079 (19)	−0.003 (2)	−0.001 (2)
C15	0.051 (2)	0.074 (3)	0.055 (2)	0.0128 (19)	0.0024 (18)	−0.014 (2)
C16	0.0437 (18)	0.085 (3)	0.0389 (19)	−0.0034 (18)	0.0069 (15)	0.0009 (19)
C17	0.0434 (18)	0.063 (2)	0.0418 (18)	−0.0013 (18)	−0.0009 (15)	0.0050 (15)
O1S	0.098 (2)	0.071 (2)	0.117 (3)	0.0067 (18)	0.019 (2)	0.0037 (18)

Br1—C17	1.893 (4)	C9—C10	1.460 (5)
O1—C1	1.372 (4)	C10—C11	1.303 (4)
O1—C8	1.375 (4)	C10—H10	0.9300
O2—C9	1.234 (4)	C11—C12	1.456 (4)
C1—C2	1.370 (5)	C11—H11	0.9300
C1—C6	1.390 (5)	C12—C13	1.385 (5)
C2—C3	1.356 (5)	C12—C17	1.390 (4)
C2—H2	0.9300	C13—C14	1.363 (5)
C3—C4	1.393 (5)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.374 (5)
C4—C5	1.361 (5)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.375 (5)
C5—C6	1.392 (5)	C15—H15	0.9300
C5—H5	0.9300	C16—C17	1.366 (5)
C6—C7	1.426 (4)	C16—H16	0.9300
C7—C8	1.353 (5)	O1S—H1SA	0.958 (19)
C7—H7	0.9300	O1S—H1SB	0.954 (19)
C8—C9	1.446 (5)
C1—O1—C8	106.5 (3)	C8—C9—C10	118.1 (3)
C2—C1—O1	126.0 (3)	C11—C10—C9	122.2 (3)
C2—C1—C6	124.5 (3)	C11—C10—H10	118.9
O1—C1—C6	109.5 (3)	C9—C10—H10	118.9
C3—C2—C1	115.5 (4)	C10—C11—C12	127.4 (4)
C3—C2—H2	122.2	C10—C11—H11	116.3
C1—C2—H2	122.2	C12—C11—H11	116.3
C2—C3—C4	122.4 (3)	C13—C12—C17	115.6 (3)
C2—C3—H3	118.8	C13—C12—C11	121.1 (3)
C4—C3—H3	118.8	C17—C12—C11	123.4 (3)
C5—C4—C3	121.1 (3)	C14—C13—C12	122.8 (3)
C5—C4—H4	119.4	C14—C13—H13	118.6
C3—C4—H4	119.4	C12—C13—H13	118.6
C4—C5—C6	118.4 (4)	C13—C14—C15	119.7 (4)
C4—C5—H5	120.8	C13—C14—H14	120.2
C6—C5—H5	120.8	C15—C14—H14	120.2
C1—C6—C5	118.1 (3)	C14—C15—C16	119.7 (3)
C1—C6—C7	106.4 (3)	C14—C15—H15	120.2
C5—C6—C7	135.5 (4)	C16—C15—H15	120.2
C8—C7—C6	106.4 (3)	C17—C16—C15	119.4 (3)
C8—C7—H7	126.8	C17—C16—H16	120.3
C6—C7—H7	126.8	C15—C16—H16	120.3
C7—C8—O1	111.2 (3)	C16—C17—C12	122.8 (3)
C7—C8—C9	133.2 (3)	C16—C17—Br1	116.6 (3)
O1—C8—C9	115.6 (3)	C12—C17—Br1	120.6 (3)
O2—C9—C8	119.8 (3)	H1SA—O1S—H1SB	94 (2)
O2—C9—C10	122.1 (3)
C8—O1—C1—C2	178.7 (3)	O1—C8—C9—O2	−3.8 (5)
C8—O1—C1—C6	−0.4 (3)	C7—C8—C9—C10	−3.6 (6)
O1—C1—C2—C3	−179.9 (3)	O1—C8—C9—C10	176.5 (3)
C6—C1—C2—C3	−1.0 (5)	O2—C9—C10—C11	−5.2 (5)
C1—C2—C3—C4	−0.3 (5)	C8—C9—C10—C11	174.5 (3)
C2—C3—C4—C5	1.0 (6)	C9—C10—C11—C12	179.5 (3)
C3—C4—C5—C6	−0.3 (5)	C10—C11—C12—C13	−2.0 (5)
C2—C1—C6—C5	1.6 (5)	C10—C11—C12—C17	179.6 (3)
O1—C1—C6—C5	−179.3 (3)	C17—C12—C13—C14	−0.5 (5)
C2—C1—C6—C7	−178.3 (3)	C11—C12—C13—C14	−179.0 (3)
O1—C1—C6—C7	0.8 (3)	C12—C13—C14—C15	1.0 (5)
C4—C5—C6—C1	−0.9 (5)	C13—C14—C15—C16	−1.0 (5)
C4—C5—C6—C7	179.0 (3)	C14—C15—C16—C17	0.5 (5)
C1—C6—C7—C8	−0.9 (3)	C15—C16—C17—C12	−0.1 (5)
C5—C6—C7—C8	179.1 (3)	C15—C16—C17—Br1	178.9 (3)
C6—C7—C8—O1	0.8 (4)	C13—C12—C17—C16	0.1 (5)
C6—C7—C8—C9	−179.1 (3)	C11—C12—C17—C16	178.6 (3)
C1—O1—C8—C7	−0.3 (4)	C13—C12—C17—Br1	−178.9 (2)
C1—O1—C8—C9	179.6 (3)	C11—C12—C17—Br1	−0.4 (4)
C7—C8—C9—O2	176.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1S—H1SA···O1	0.96 (2)	2.37 (4)	3.181 (4)	142 (4)
O1S—H1SB···O2	0.95 (2)	2.11 (4)	2.928 (4)	143 (4)
C7—H7···O1Si	0.93	2.32	3.229 (5)	164
C10—H10···O1Si	0.93	2.45	3.375 (5)	174

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O1SH1SAO1	0.96(2)	2.37(4)	3.181(4)	142(4)
O1SH1SBO2	0.95(2)	2.11(4)	2.928(4)	143(4)
C7H7O1S i	0.93	2.32	3.229(5)	164
C10H10O1S i	0.93	2.45	3.375(5)	174

Symmetry code: (i) .