Crystal structure of 2-(5-bromo-2-hy­droxy­benzyl­idene)-2,3-di­hydro-1H-indene-1,3-dione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Abdelhamid, A.A.; Albayati, M.R.

doi:10.1107/S2056989015007434

organic compounds

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Volume 71| Part 5| May 2015| Pages o324-o325

https://doi.org/10.1107/S2056989015007434

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Crystal structure of 2-(5-bromo-2-hydroxybenzylidene)-2,3-dihydro-1H-indene-1,3-dione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Antar A. Abdelhamid ^e and Mustafa R. Albayati ^f ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by M. Weil, Vienna University of Technology, Austria (Received 9 April 2015; accepted 15 April 2015; online 22 April 2015)

The title molecule, C₁₆H₉BrO₃, deviates slightly from planarity. The benzene ring makes a dihedral angle of 1.02 (9)° with the plane defined by the five-membered ring of the indandione moiety. The latter exhibits a minute twist indicated by the dihedral angle of 0.47 (9)° between the planes of the five- and six-membered rings. An intramolecular C—H⋯O hydrogen bond between the attached benzene ring with one of the indandione carbonyl O atoms stabilizes the molecular conformation. In the crystal, the molecules form dimers across centres of inversion via pairwise O—H⋯O hydrogen bonds. The dimers form stacks running parallel to [010] and interact through π–π interactions between the five-membered ring of one molecule and the six-membered rings of the indandione moiety of an adjacent molecule [centroid-to-centroid distance = 3.5454 (10) Å].

Keywords: crystal structure; 3-substituted indan-1,3-diones; hydrogen bonding; π–π interactions.

CCDC reference: 1059869

1. Related literature

Indan-1,3-dione and its analogues are synthons for building highly interesting compounds with a wide range of applications in both pharmaceutical and industrial chemistry (Kuhn & Rae, 1971 ; Junek & Sterk, 1968 ; Kunz & Polansky, 1969 ; Aldersley et al., 1983 ). For chemical reactions and bio-activities of 3-substituted indan-1,3-diones, see: Hochrainer & Wessely (1966 ); Zargar & Khan (2015 ).

2. Experimental

2.1. Crystal data

C₁₆H₉BrO₃
M_r = 329.14
Monoclinic, P 2₁ /c
a = 13.8820 (4) Å
b = 3.8695 (1) Å
c = 24.0068 (5) Å
β = 102.483 (1)°
V = 1259.07 (6) Å³
Z = 4
Cu Kα radiation
μ = 4.50 mm⁻¹
T = 150 K
0.22 × 0.07 × 0.04 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: numerical (SADABS; Bruker, 2014 ) T_min = 0.67, T_max = 0.84
8943 measured reflections
2510 independent reflections
2386 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.056
S = 1.09
2510 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3	0.95	2.15	2.994 (2)	148
O1—H1⋯O2ⁱ	0.84	1.83	2.6641 (16)	173
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

CCDC reference: 1059869

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989015007434/wm5145sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989015007434/wm5145Isup2.hkl

checkCIF report

Related literature top

Indan-1,3-dione and its analogues are synthons for building highly interesting compounds with a wide range of applications in both pharmaceutical and industrial chemistry (Kuhn & Rae, 1971; Junek & Sterk, 1968; Kunz & Polansky, 1969; Aldersley et al., 1983). For chemical reactions and bio-activities of 3-substituted indan-1,3-diones, see: Hochrainer & Wessely (1966); Zargar & Khan (2015).

Experimental top

A mixture of 1 mmol (146 mg) of 1H-indene-1,3(2H)-dione and 1 mmol (201 mg) of 5-bromo-2-hydroxybenzaldehyde in 30 ml ethanol was refluxed for 30 min. The resulting solid product was collected under vacuum and re-crystallized from ethanol to afford yellow needles suitable for X-ray diffraction in 83% yield.

Structure description top

Indan-1,3-dione and its analogues are synthons for building highly interesting compounds with a wide range of applications in both pharmaceutical and industrial chemistry (Kuhn & Rae, 1971; Junek & Sterk, 1968; Kunz & Polansky, 1969; Aldersley et al., 1983). For chemical reactions and bio-activities of 3-substituted indan-1,3-diones, see: Hochrainer & Wessely (1966); Zargar & Khan (2015).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular C—H···O interaction is shown as a dotted line.
	Fig. 2. Crystal packing of the title compound viewed down [010]. Intermolecular O—H···O hydrogen bonds are shown as dotted lines.

2-(5-Bromo-2-hydroxybenzylidene)-2,3-dihydro-1H-indene-1,3-dione top

Crystal data top

C₁₆H₉BrO₃	F(000) = 656
M_r = 329.14	D_x = 1.736 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 13.8820 (4) Å	Cell parameters from 7789 reflections
b = 3.8695 (1) Å	θ = 3.3–74.5°
c = 24.0068 (5) Å	µ = 4.50 mm⁻¹
β = 102.483 (1)°	T = 150 K
V = 1259.07 (6) Å³	Needle, yellow
Z = 4	0.22 × 0.07 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2510 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2386 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.020
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.5°, θ_min = 3.3°
ω scans	h = −16→17
Absorption correction: numerical (SADABS; Bruker, 2014)	k = −4→4
T_min = 0.67, T_max = 0.84	l = −29→29
8943 measured reflections

Refinement top

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)] = 0.021	Hydrogen site location: mixed
wR(F²) = 0.056	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0301P)² + 0.6412P] where P = (F_o² + 2F_c²)/3
2510 reflections	(Δ/σ)_max = 0.003
181 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₉BrO₃	V = 1259.07 (6) Å³
M_r = 329.14	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.8820 (4) Å	µ = 4.50 mm⁻¹
b = 3.8695 (1) Å	T = 150 K
c = 24.0068 (5) Å	0.22 × 0.07 × 0.04 mm
β = 102.483 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2510 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2014)	2386 reflections with I > 2σ(I)
T_min = 0.67, T_max = 0.84	R_int = 0.020
8943 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.09	Δρ_max = 0.36 e Å⁻³
2510 reflections	Δρ_min = −0.25 e Å⁻³
181 parameters

Special details top

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while that attached to oxygen was placed in a location derived from a difference map and its coordinates adjusted to give O—H = 0.84 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.74761 (2)	0.32460 (5)	0.72665 (2)	0.02597 (8)
O1	1.00458 (9)	−0.0525 (4)	0.56417 (5)	0.0324 (3)
H1	1.0561	−0.1618	0.5789	0.039*
O2	0.82877 (9)	0.4018 (4)	0.39794 (5)	0.0275 (3)
O3	0.63542 (9)	0.6391 (4)	0.53435 (5)	0.0331 (3)
C1	0.85867 (12)	0.2074 (4)	0.57969 (6)	0.0188 (3)
C2	0.94845 (11)	0.0308 (4)	0.60120 (6)	0.0216 (3)
C3	0.97616 (11)	−0.0550 (4)	0.65901 (6)	0.0227 (3)
H3	1.0370	−0.1702	0.6731	0.027*
C4	0.91553 (12)	0.0270 (4)	0.69553 (6)	0.0215 (3)
H4	0.9339	−0.0334	0.7348	0.026*
C5	0.82703 (12)	0.1991 (4)	0.67450 (6)	0.0195 (3)
C6	0.79773 (12)	0.2902 (4)	0.61786 (6)	0.0195 (3)
H6	0.7370	0.4079	0.6046	0.023*
C7	0.83772 (12)	0.2944 (4)	0.51956 (6)	0.0196 (3)
H7	0.8883	0.2221	0.5011	0.024*
C8	0.76223 (11)	0.4559 (4)	0.48379 (6)	0.0193 (3)
C9	0.76467 (11)	0.4982 (4)	0.42218 (6)	0.0195 (3)
C10	0.67288 (11)	0.6780 (4)	0.39402 (7)	0.0191 (3)
C11	0.64124 (13)	0.7720 (4)	0.33723 (7)	0.0235 (3)
H11	0.6801	0.7253	0.3100	0.028*
C12	0.55046 (13)	0.9372 (4)	0.32177 (7)	0.0262 (3)
H12	0.5268	1.0061	0.2833	0.031*
C13	0.49331 (12)	1.0039 (5)	0.36193 (7)	0.0269 (3)
H13	0.4315	1.1172	0.3502	0.032*
C14	0.52519 (12)	0.9075 (5)	0.41869 (7)	0.0243 (3)
H14	0.4862	0.9515	0.4459	0.029*
C15	0.61626 (12)	0.7441 (4)	0.43405 (7)	0.0202 (3)
C16	0.66754 (12)	0.6133 (4)	0.49114 (7)	0.0216 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.03096 (11)	0.02856 (12)	0.02164 (10)	0.00308 (7)	0.01281 (7)	−0.00170 (6)
O1	0.0248 (6)	0.0525 (8)	0.0217 (5)	0.0200 (6)	0.0089 (4)	0.0075 (6)
O2	0.0239 (6)	0.0394 (7)	0.0207 (5)	0.0109 (5)	0.0084 (4)	0.0042 (5)
O3	0.0278 (6)	0.0513 (8)	0.0223 (6)	0.0172 (6)	0.0102 (5)	0.0053 (5)
C1	0.0181 (7)	0.0208 (8)	0.0175 (7)	0.0013 (6)	0.0038 (6)	−0.0007 (6)
C2	0.0193 (7)	0.0260 (8)	0.0200 (7)	0.0031 (7)	0.0057 (6)	0.0000 (6)
C3	0.0193 (7)	0.0266 (8)	0.0208 (7)	0.0037 (7)	0.0012 (6)	0.0023 (6)
C4	0.0236 (7)	0.0225 (8)	0.0172 (6)	−0.0010 (7)	0.0019 (6)	0.0004 (6)
C5	0.0206 (7)	0.0203 (8)	0.0193 (7)	−0.0011 (6)	0.0079 (6)	−0.0030 (6)
C6	0.0186 (7)	0.0201 (8)	0.0199 (7)	0.0023 (6)	0.0042 (6)	−0.0011 (6)
C7	0.0193 (7)	0.0217 (8)	0.0189 (7)	0.0021 (6)	0.0062 (6)	−0.0013 (6)
C8	0.0190 (7)	0.0208 (7)	0.0184 (7)	0.0014 (6)	0.0049 (5)	−0.0006 (6)
C9	0.0190 (7)	0.0201 (7)	0.0189 (7)	0.0011 (6)	0.0032 (5)	0.0006 (6)
C10	0.0181 (7)	0.0173 (7)	0.0215 (7)	−0.0004 (6)	0.0033 (6)	−0.0010 (5)
C11	0.0262 (8)	0.0230 (8)	0.0207 (7)	0.0017 (7)	0.0039 (6)	0.0016 (6)
C12	0.0299 (8)	0.0222 (8)	0.0224 (7)	0.0013 (7)	−0.0033 (6)	0.0022 (6)
C13	0.0218 (8)	0.0230 (8)	0.0317 (8)	0.0043 (7)	−0.0032 (6)	−0.0005 (7)
C14	0.0191 (7)	0.0259 (8)	0.0271 (8)	0.0039 (7)	0.0031 (6)	−0.0019 (7)
C15	0.0181 (7)	0.0203 (7)	0.0211 (7)	0.0010 (6)	0.0019 (6)	−0.0010 (6)
C16	0.0196 (7)	0.0238 (8)	0.0211 (7)	0.0040 (6)	0.0037 (6)	0.0005 (6)

Geometric parameters (Å, º) top

Br1—C5	1.9014 (15)	C7—H7	0.9500
O1—C2	1.3418 (19)	C8—C16	1.493 (2)
O1—H1	0.8400	C8—C9	1.4956 (19)
O2—C9	1.2221 (19)	C9—C10	1.481 (2)
O3—C16	1.218 (2)	C10—C11	1.387 (2)
C1—C6	1.412 (2)	C10—C15	1.390 (2)
C1—C2	1.417 (2)	C11—C12	1.390 (2)
C1—C7	1.449 (2)	C11—H11	0.9500
C2—C3	1.398 (2)	C12—C13	1.399 (3)
C3—C4	1.377 (2)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.390 (2)
C4—C5	1.393 (2)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.390 (2)
C5—C6	1.378 (2)	C14—H14	0.9500
C6—H6	0.9500	C15—C16	1.490 (2)
C7—C8	1.355 (2)

C2—O1—H1	113.9	O2—C9—C10	124.70 (14)
C6—C1—C2	118.43 (14)	O2—C9—C8	127.73 (14)
C6—C1—C7	125.05 (14)	C10—C9—C8	107.57 (13)
C2—C1—C7	116.51 (14)	C11—C10—C15	121.66 (15)
O1—C2—C3	121.74 (14)	C11—C10—C9	129.07 (15)
O1—C2—C1	117.73 (13)	C15—C10—C9	109.27 (13)
C3—C2—C1	120.53 (14)	C10—C11—C12	117.32 (15)
C4—C3—C2	120.16 (14)	C10—C11—H11	121.3
C4—C3—H3	119.9	C12—C11—H11	121.3
C2—C3—H3	119.9	C11—C12—C13	121.16 (15)
C3—C4—C5	119.47 (14)	C11—C12—H12	119.4
C3—C4—H4	120.3	C13—C12—H12	119.4
C5—C4—H4	120.3	C14—C13—C12	121.23 (15)
C6—C5—C4	121.94 (14)	C14—C13—H13	119.4
C6—C5—Br1	119.65 (12)	C12—C13—H13	119.4
C4—C5—Br1	118.37 (11)	C13—C14—C15	117.44 (15)
C5—C6—C1	119.46 (14)	C13—C14—H14	121.3
C5—C6—H6	120.3	C15—C14—H14	121.3
C1—C6—H6	120.3	C14—C15—C10	121.19 (15)
C8—C7—C1	134.39 (15)	C14—C15—C16	128.67 (15)
C8—C7—H7	112.8	C10—C15—C16	110.15 (14)
C1—C7—H7	112.8	O3—C16—C15	124.43 (15)
C7—C8—C16	133.85 (14)	O3—C16—C8	128.87 (14)
C7—C8—C9	119.83 (14)	C15—C16—C8	106.70 (13)
C16—C8—C9	106.32 (13)

C6—C1—C2—O1	178.65 (15)	C8—C9—C10—C11	−179.35 (16)
C7—C1—C2—O1	−2.4 (2)	O2—C9—C10—C15	179.00 (16)
C6—C1—C2—C3	−0.7 (2)	C8—C9—C10—C15	−0.22 (18)
C7—C1—C2—C3	178.19 (15)	C15—C10—C11—C12	0.3 (2)
O1—C2—C3—C4	−178.38 (17)	C9—C10—C11—C12	179.34 (16)
C1—C2—C3—C4	1.0 (3)	C10—C11—C12—C13	−0.3 (3)
C2—C3—C4—C5	−0.7 (3)	C11—C12—C13—C14	0.0 (3)
C3—C4—C5—C6	0.1 (3)	C12—C13—C14—C15	0.4 (3)
C3—C4—C5—Br1	−177.54 (13)	C13—C14—C15—C10	−0.4 (3)
C4—C5—C6—C1	0.1 (2)	C13—C14—C15—C16	−179.70 (17)
Br1—C5—C6—C1	177.74 (12)	C11—C10—C15—C14	0.1 (3)
C2—C1—C6—C5	0.2 (2)	C9—C10—C15—C14	−179.15 (15)
C7—C1—C6—C5	−178.61 (15)	C11—C10—C15—C16	179.48 (15)
C6—C1—C7—C8	−1.5 (3)	C9—C10—C15—C16	0.27 (19)
C2—C1—C7—C8	179.65 (18)	C14—C15—C16—O3	−1.4 (3)
C1—C7—C8—C16	−0.2 (3)	C10—C15—C16—O3	179.24 (17)
C1—C7—C8—C9	−179.21 (17)	C14—C15—C16—C8	179.14 (17)
C7—C8—C9—O2	0.1 (3)	C10—C15—C16—C8	−0.22 (19)
C16—C8—C9—O2	−179.12 (17)	C7—C8—C16—O3	1.5 (3)
C7—C8—C9—C10	179.33 (15)	C9—C8—C16—O3	−179.35 (18)
C16—C8—C9—C10	0.08 (17)	C7—C8—C16—C15	−179.02 (18)
O2—C9—C10—C11	−0.1 (3)	C9—C8—C16—C15	0.08 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3	0.95	2.15	2.994 (2)	148
O1—H1···O2ⁱ	0.84	1.83	2.6641 (16)	173

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3	0.95	2.15	2.994 (2)	148
O1—H1···O2ⁱ	0.84	1.83	2.6641 (16)	173

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of 2-(5-bromo-2-hy­dr­oxy­benzyl­­idene)-2,3-di­hydro-1H-indene-1,3-dione

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of 2-(5-bromo-2-hydroxybenzylidene)-2,3-dihydro-1H-indene-1,3-dione