Crystal structure of 2-bromo-1,4-dihy­droxy-9,10-anthra­quinone

Furukawa, W.; Takehara, M.; Inoue, Y.; Kitamura, C.

doi:10.1107/S1600536814020996

organic compounds

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Volume 70| Part 10| October 2014| Page o1130

doi:10.1107/S1600536814020996

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Crystal structure of 2-bromo-1,4-dihydroxy-9,10-anthraquinone

Wataru Furukawa,^a Munenori Takehara,^a Yoshinori Inoue ^a and Chitoshi Kitamura ^a ^*

^aDepartment of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan
^*Correspondence e-mail: kitamura.c@mat.usp.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 7 September 2014; accepted 20 September 2014; online 27 September 2014)

In an attempt to brominate 1,4-dipropoxy-9,10-anthraquinone, a mixture of products, including the title compound, C₁₄H₇BrO₄, was obtained. The molecule is essentially planar (r.m.s. deviation = 0.029 Å) and two intramolecular O—H⋯O hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H⋯O hydrogen bonds, Br⋯O contacts [3.240 (5) Å], and π–π stacking interactions [shortest centroid–centroid separation = 3.562 (4) Å], generating a three-dimensional network.

Keywords: crystal structure; 1,4-dihydroxy-9,10-anthraquione; hydrogen bonds.

CCDC reference: 1025364

1. Related literature

For the original synthesis of the title compound, see: Peters & Tenny (1977 ). For related crystal structures of 1,4-dihydroxy-9,10-anthraquinone derivatives, see: Nigam & Deppisch (1980 ); Hall et al. (1988 ). For 1,4-dipropoxy-9,10-anthraquinone, see: Kitamura et al. (2004 ).

2. Experimental

2.1. Crystal data

C₁₄H₇BrO₄
M_r = 319.11
Orthorhombic, P c a 2₁
a = 18.977 (3) Å
b = 3.7811 (4) Å
c = 15.5047 (18) Å
V = 1112.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 3.70 mm⁻¹
T = 200 K
0.5 × 0.4 × 0.05 mm

2.2. Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: numerical (NUMABS; Higashi, 1999 ) T_min = 0.322, T_max = 0.912
15045 measured reflections
2476 independent reflections
2103 reflections with I > 2σ(I)
R_int = 0.091

2.3. Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.099
S = 1.11
2476 reflections
179 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.85 e Å⁻³
Δρ_min = −1.36 e Å⁻³
Absolute structure: Flack x determined using 846 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack, 2004 )
Absolute structure parameter: 0.000 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.80 (9)	1.82 (9)	2.536 (8)	148 (9)
O2—H2⋯O3	0.99 (10)	1.65 (10)	2.568 (9)	152 (8)
C3—H3⋯O4ⁱ	0.95	2.46	3.396 (9)	169
C9—H9⋯O1ⁱⁱ	0.95	2.59	3.308 (10)	133
C9—H9⋯O2ⁱⁱⁱ	0.95	2.69	3.394 (10)	132
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y, z]$ ; (iii) $[-x+{\script{1\over 2}}, y-1, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 1025364

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814020996/hb7282sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814020996/hb7282Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814020996/hb7282Isup3.cml

checkCIF report

Comment top

Anthraquinone and its derivatives are important dyestuff molecules. In this work, we attempted to brominate 1,4-dipropoxy-9,10-anthraquinone (Kitamura et al., 2004) with elementary bromine in acetic acid to obtain 2-bromo-1,4-dipropoxy-9,10-anthraquinone. As a result, the reaction afforded a complex mixture of products containing 2-bromo-1,4-dihydroxy-9,10-anthraquinone, C₁₄H₇BrO₄ (I). Synthesis of the title compound, (I), was already reported by Peters & Tenny (1977) using a different method. However, the X-ray structure of (I) was not reported so far. We report here the crystal structure of the title compound, (I).

The title compound crystallizes in the orthorhombic space group Pca2₁ with a Flack parameter of 0.000 (11). The molecular structure of (I) is shown in Figure 1. The molecule is nearly planar with the maximum deviation of 0.053 (7) Å for O2. The bond length of C6—O3 and C13—O4 is 1.246 (9) Å and 1.238 (9) Å, respectively. The length of the single C—O bond of C1—O1 and C4—O2 is 1.340 (9) Å and 1.348 (10) Å, respectively. There are two intramolecular hydrogen bonds, O1—H1···O4 and O2—H2···O3. The distance of O1—O4 and O2—O3 is 2.536 (8) Å and 2.568 (9) Å, respectively. These values are in good agreement with those observed for 1,4-dihydroxy-9,10-anthraquinone (Nigam & Deppisch, 1980) and 2,3-dichloro-1,4-dihydroxy-9,10-anthraquinone (Hall et al., 1988).

As shown in Figure 2, in the crystal, molecules are linked by C—H···O hydrogen bonds (Table 1) and Br···O contacts [Br1···O3ⁱ = 3.240 (5) Å; symmetry code: (i) x - 1/2, -y + 1, z], whose value is shorter than the sum of van der Waals radii of bromine and oxygen atoms. The molecules are π-stacked along the a axis with an interplanar distance of 3.450 Å.

Related literature top

For the original synthesis of the title compound, see: Peters & Tenny (1977). For related crystal structures of 1,4-dihydroxy-9,10-anthraquinone derivatives, see: Nigam & Deppisch (1980); Hall et al. (1988). For 1,4-dipropoxy-9,10-anthraquinone, see: Kitamura et al. (2004).

Experimental top

A mixture of 1,4-dipropoxy-9,10-anthraquinone (653 mg, 2.01 mmol), iron powder (50 mg, 0.89 mmol), bromine (0.40 g, 2.5 mmol) in acetic acid (20 ml) was stirred at 80 °C under air. The reaction was quenched with an aqueous solution of Na₂SO₃. Then the reaction products were precipitated. After filtration, the residue was subjected to column chromatography on silica gel using CH₂Cl₂-hexane as the eluent to afford the title compound (18 mg, 2.8% yield) as a red solid. Red platelets were obtained by slow evaporation of a CH₂Cl₂ solution.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids. The intramolecular hydrogen bonds are drawn by dashed lines.
	Fig. 2. The crystal packing of (I), showing short contacts of selected C–H···O and Br···O interactions by blue lines.

2-Bromo-1,4-dihydroxy-9,10-anthraquinone top

Crystal data top

C₁₄H₇BrO₄	D_x = 1.905 Mg m⁻³
M_r = 319.11	Melting point: 485 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 12445 reflections
a = 18.977 (3) Å	θ = 3.4–27.5°
b = 3.7811 (4) Å	µ = 3.70 mm⁻¹
c = 15.5047 (18) Å	T = 200 K
V = 1112.5 (2) Å³	Platelet, red
Z = 4	0.5 × 0.4 × 0.05 mm
F(000) = 632

Data collection top

Rigaku R-AXIS RAPID diffractometer	2476 independent reflections
Radiation source: fine-focus sealed x-ray tube	2103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 10 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ω scans	h = −24→24
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −4→4
T_min = 0.322, T_max = 0.912	l = −20→20
15045 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.057	w = 1/[σ²(F_o²) + (0.0171P)² + 1.2737P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.099	(Δ/σ)_max = 0.001
S = 1.11	Δρ_max = 0.85 e Å⁻³
2476 reflections	Δρ_min = −1.36 e Å⁻³
179 parameters	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.017 (2)
0 constraints	Absolute structure: Flack x determined using 846 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.000 (11)

Crystal data top

C₁₄H₇BrO₄	V = 1112.5 (2) Å³
M_r = 319.11	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 18.977 (3) Å	µ = 3.70 mm⁻¹
b = 3.7811 (4) Å	T = 200 K
c = 15.5047 (18) Å	0.5 × 0.4 × 0.05 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2476 independent reflections
Absorption correction: numerical (NUMABS; Higashi, 1999)	2103 reflections with I > 2σ(I)
T_min = 0.322, T_max = 0.912	R_int = 0.091
15045 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	Δρ_max = 0.85 e Å⁻³
S = 1.11	Δρ_min = −1.36 e Å⁻³
2476 reflections	Absolute structure: Flack x determined using 846 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons & Flack, 2004)
179 parameters	Absolute structure parameter: 0.000 (11)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
Br1	−0.12607 (3)	0.68820 (18)	0.29479 (9)	0.0301 (2)
O1	−0.0661 (3)	0.3974 (18)	0.4573 (4)	0.0354 (15)
O2	0.1215 (3)	0.3132 (19)	0.1883 (4)	0.0381 (15)
O3	0.2118 (2)	0.0436 (14)	0.2927 (4)	0.0350 (11)
O4	0.0247 (3)	0.1085 (17)	0.5543 (3)	0.0361 (15)
C1	−0.0179 (4)	0.373 (2)	0.3944 (5)	0.0242 (16)
C2	−0.0352 (4)	0.4934 (18)	0.3106 (5)	0.0258 (17)
C3	0.0105 (4)	0.476 (2)	0.2437 (5)	0.0259 (17)
H3	−0.0024	0.5634	0.1885	0.031*
C4	0.0786 (5)	0.325 (2)	0.2576 (5)	0.0262 (18)
C5	0.0979 (4)	0.209 (2)	0.3392 (5)	0.0222 (17)
C6	0.1685 (4)	0.061 (2)	0.3529 (5)	0.0271 (17)
C7	0.1876 (4)	−0.062 (2)	0.4400 (5)	0.0236 (15)
C8	0.2550 (4)	−0.196 (2)	0.4556 (5)	0.0280 (17)
H8	0.2885	−0.2062	0.4101	0.034*
C9	0.2731 (4)	−0.312 (2)	0.5369 (6)	0.0304 (18)
H9	0.319	−0.4027	0.5471	0.037*
C10	0.2248 (5)	−0.299 (2)	0.6038 (6)	0.0310 (19)
H10	0.2378	−0.3771	0.6598	0.037*
C11	0.1572 (4)	−0.171 (2)	0.5885 (5)	0.0282 (17)
H11	0.1239	−0.1641	0.6342	0.034*
C12	0.1385 (4)	−0.054 (2)	0.5078 (5)	0.0228 (16)
C13	0.0675 (4)	0.0989 (19)	0.4941 (5)	0.0234 (15)
C14	0.0487 (4)	0.2263 (19)	0.4077 (5)	0.0226 (15)
H1	−0.051 (5)	0.30 (2)	0.499 (6)	0.034*
H2	0.164 (5)	0.20 (2)	0.212 (6)	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0287 (4)	0.0284 (4)	0.0332 (4)	0.0024 (3)	−0.0052 (4)	0.0010 (8)
O1	0.030 (3)	0.052 (4)	0.024 (3)	0.008 (3)	0.002 (2)	0.003 (3)
O2	0.033 (3)	0.061 (4)	0.021 (3)	0.002 (3)	0.006 (2)	0.007 (3)
O3	0.031 (3)	0.048 (3)	0.025 (2)	0.003 (2)	0.006 (3)	0.000 (5)
O4	0.032 (4)	0.055 (5)	0.022 (3)	0.007 (3)	0.006 (2)	0.003 (3)
C1	0.025 (4)	0.026 (5)	0.021 (3)	−0.004 (3)	0.000 (3)	−0.003 (4)
C2	0.029 (4)	0.021 (4)	0.028 (5)	−0.002 (2)	−0.004 (3)	0.001 (4)
C3	0.038 (5)	0.017 (4)	0.023 (4)	−0.002 (3)	0.001 (3)	0.007 (3)
C4	0.027 (5)	0.028 (5)	0.023 (4)	−0.003 (3)	0.003 (3)	0.007 (4)
C5	0.025 (4)	0.018 (4)	0.023 (4)	−0.002 (3)	0.003 (3)	0.002 (4)
C6	0.030 (4)	0.025 (4)	0.026 (4)	−0.002 (3)	0.001 (3)	−0.003 (4)
C7	0.025 (4)	0.021 (4)	0.025 (4)	−0.003 (3)	0.002 (3)	−0.005 (3)
C8	0.025 (4)	0.028 (4)	0.031 (4)	0.000 (3)	0.003 (3)	0.004 (4)
C9	0.022 (4)	0.031 (4)	0.039 (5)	0.001 (3)	−0.003 (4)	0.002 (5)
C10	0.034 (5)	0.030 (5)	0.029 (4)	−0.001 (3)	−0.005 (4)	0.006 (5)
C11	0.029 (4)	0.031 (4)	0.024 (4)	0.000 (3)	0.000 (3)	−0.002 (4)
C12	0.030 (4)	0.017 (4)	0.022 (4)	−0.002 (3)	0.001 (3)	0.002 (3)
C13	0.030 (4)	0.022 (4)	0.019 (3)	−0.002 (3)	0.000 (3)	−0.001 (3)
C14	0.026 (4)	0.021 (4)	0.020 (3)	−0.001 (3)	0.001 (3)	−0.002 (3)

Geometric parameters (Å, º) top

Br1—C2	1.890 (7)	C5—C6	1.467 (12)
O1—C1	1.340 (9)	C6—C7	1.474 (11)
O1—H1	0.80 (9)	C7—C8	1.396 (11)
O2—C4	1.348 (10)	C7—C12	1.405 (10)
O2—H2	0.99 (10)	C8—C9	1.379 (12)
O3—C6	1.246 (9)	C8—H8	0.95
O4—C13	1.238 (9)	C9—C10	1.384 (13)
C1—C14	1.397 (10)	C9—H9	0.95
C1—C2	1.414 (10)	C10—C11	1.391 (12)
C2—C3	1.354 (10)	C10—H10	0.95
C3—C4	1.431 (12)	C11—C12	1.375 (11)
C3—H3	0.95	C11—H11	0.95
C4—C5	1.387 (10)	C12—C13	1.481 (10)
C5—C14	1.416 (10)	C13—C14	1.467 (10)

C1—O1—H1	108 (7)	C12—C7—C6	120.9 (7)
C4—O2—H2	102 (5)	C9—C8—C7	120.0 (7)
O1—C1—C14	122.5 (7)	C9—C8—H8	120
O1—C1—C2	119.2 (7)	C7—C8—H8	120
C14—C1—C2	118.3 (7)	C8—C9—C10	120.6 (8)
C3—C2—C1	122.6 (7)	C8—C9—H9	119.7
C3—C2—Br1	120.2 (6)	C10—C9—H9	119.7
C1—C2—Br1	117.1 (5)	C9—C10—C11	119.7 (8)
C2—C3—C4	118.8 (7)	C9—C10—H10	120.2
C2—C3—H3	120.6	C11—C10—H10	120.2
C4—C3—H3	120.6	C12—C11—C10	120.4 (7)
O2—C4—C5	123.9 (8)	C12—C11—H11	119.8
O2—C4—C3	116.0 (7)	C10—C11—H11	119.8
C5—C4—C3	120.2 (7)	C11—C12—C7	120.1 (7)
C4—C5—C14	119.7 (7)	C11—C12—C13	119.4 (7)
C4—C5—C6	119.6 (7)	C7—C12—C13	120.4 (7)
C14—C5—C6	120.7 (7)	O4—C13—C14	121.3 (7)
O3—C6—C5	120.9 (8)	O4—C13—C12	120.0 (7)
O3—C6—C7	120.5 (7)	C14—C13—C12	118.6 (6)
C5—C6—C7	118.6 (7)	C1—C14—C5	120.3 (7)
C8—C7—C12	119.2 (7)	C1—C14—C13	119.1 (7)
C8—C7—C6	119.9 (7)	C5—C14—C13	120.6 (7)

O1—C1—C2—C3	−179.7 (7)	C9—C10—C11—C12	−0.7 (14)
C14—C1—C2—C3	−1.1 (11)	C10—C11—C12—C7	−0.1 (13)
O1—C1—C2—Br1	1.0 (9)	C10—C11—C12—C13	−176.8 (7)
C14—C1—C2—Br1	179.6 (5)	C8—C7—C12—C11	1.0 (12)
C1—C2—C3—C4	1.2 (12)	C6—C7—C12—C11	179.8 (8)
Br1—C2—C3—C4	−179.5 (6)	C8—C7—C12—C13	177.6 (7)
C2—C3—C4—O2	179.5 (7)	C6—C7—C12—C13	−3.6 (11)
C2—C3—C4—C5	−2.2 (13)	C11—C12—C13—O4	−2.7 (12)
O2—C4—C5—C14	−178.8 (7)	C7—C12—C13—O4	−179.3 (8)
C3—C4—C5—C14	3.0 (14)	C11—C12—C13—C14	179.3 (7)
O2—C4—C5—C6	−0.7 (15)	C7—C12—C13—C14	2.6 (11)
C3—C4—C5—C6	−178.8 (7)	O1—C1—C14—C5	−179.6 (7)
C4—C5—C6—O3	1.6 (13)	C2—C1—C14—C5	1.9 (11)
C14—C5—C6—O3	179.6 (7)	O1—C1—C14—C13	−1.2 (11)
C4—C5—C6—C7	−179.6 (8)	C2—C1—C14—C13	−179.8 (6)
C14—C5—C6—C7	−1.5 (11)	C4—C5—C14—C1	−2.9 (12)
O3—C6—C7—C8	0.7 (12)	C6—C5—C14—C1	179.0 (7)
C5—C6—C7—C8	−178.2 (8)	C4—C5—C14—C13	178.7 (8)
O3—C6—C7—C12	−178.2 (7)	C6—C5—C14—C13	0.7 (11)
C5—C6—C7—C12	3.0 (11)	O4—C13—C14—C1	2.5 (11)
C12—C7—C8—C9	−0.9 (13)	C12—C13—C14—C1	−179.5 (7)
C6—C7—C8—C9	−179.8 (8)	O4—C13—C14—C5	−179.2 (7)
C7—C8—C9—C10	0.1 (14)	C12—C13—C14—C5	−1.1 (11)
C8—C9—C10—C11	0.8 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.80 (9)	1.82 (9)	2.536 (8)	148 (9)
O2—H2···O3	0.99 (10)	1.65 (10)	2.568 (9)	152 (8)
C3—H3···O4ⁱ	0.95	2.46	3.396 (9)	169
C9—H9···O1ⁱⁱ	0.95	2.59	3.308 (10)	133
C9—H9···O2ⁱⁱⁱ	0.95	2.69	3.394 (10)	132

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) x+1/2, −y, z; (iii) −x+1/2, y−1, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.80 (9)	1.82 (9)	2.536 (8)	148 (9)
O2—H2···O3	0.99 (10)	1.65 (10)	2.568 (9)	152 (8)
C3—H3···O4ⁱ	0.95	2.46	3.396 (9)	169
C9—H9···O1ⁱⁱ	0.95	2.59	3.308 (10)	133
C9—H9···O2ⁱⁱⁱ	0.95	2.69	3.394 (10)	132

Symmetry codes: (i) −x, −y+1, z−1/2; (ii) x+1/2, −y, z; (iii) −x+1/2, y−1, z+1/2.

References

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Volume 70| Part 10| October 2014| Page o1130

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