2,4,6-Tri­nitro­phenyl 4-bromo­benzoate

Moreno-Fuquen, R.

doi:10.1107/S1600536813031061

organic compounds

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Volume 69| Part 12| December 2013| Page o1787

doi:10.1107/S1600536813031061

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2,4,6-Trinitrophenyl 4-bromobenzoate

Rodolfo Moreno-Fuquen ^a ^*

^aDepartamento de Química – Facultad de Ciencias, Universidad del Valle, Apartado 25360, Santiago de Cali, Colombia
^*Correspondence e-mail: rodimo26@yahoo.es

(Received 8 November 2013; accepted 12 November 2013; online 20 November 2013)

In the title benzoate derivative, C₁₃H₆BrN₃O₈, the benzene rings form a dihedral angle of 80.90 (9)°. The ester moiety forms dihedral angles of 3.2 (2) and 82.8 4(10)° with the benzene and picryl rings, respectively. The Br atom is disordered over two positions, with the site occupancy for the minor component being 0.48 (4). The crystal structure features C—H⋯O interactions, which generate a three-dimensional network.

CCDC reference: 971547

Related literature

For similar esters, see: Moreno-Fuquen et al. (2013 ). For hydrogen bonding, see: Nardelli (1995 ).

Experimental

Crystal data

C₁₃H₆BrN₃O₈
M_r = 412.12
Monoclinic, P 2₁ /c
a = 10.8409 (5) Å
b = 10.0152 (7) Å
c = 13.9777 (7) Å
β = 99.246 (3)°
V = 1497.89 (15) Å³
Z = 4
Mo Kα radiation
μ = 2.80 mm⁻¹
T = 295 K
0.34 × 0.13 × 0.11 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.668, T_max = 0.753
10473 measured reflections
3340 independent reflections
2092 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.134
S = 1.02
3340 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.93	2.48	3.169 (4)	131
C12—H12⋯O1ⁱⁱ	0.93	2.49	3.273 (4)	142
C5—H5⋯O8ⁱⁱⁱ	0.93	2.46	3.384 (4)	173
C3—H3⋯O6^iv	0.93	2.42	3.291 (4)	157
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 971547

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813031061/tk5272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813031061/tk5272Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813031061/tk5272Isup3.cml

checkCIF report

Experimental top

Synthesis and crystallization top

The reagents and solvents for the synthesis were obtained from the Aldrich Chemical Co., and were used without additional purification. The title molecule was obtained through a two-step reaction. First 4-bromobenzoic acid (0.223 g, 0.541 mmol) was refluxed in an excess of thionyl chloride (10 ml) for 1 h. Then, thionyl chloride was distilled off under reduced pressure to purify the 4-bromobenzoyl chloride which was obtained as a pale-yellow translucent liquid. The same reaction flask was rearranged and a solution of picric acid (0.115 g, 0.541 mmol) in acetonitrile, was added drop-wise with constant stirring. The reaction mixture was left to reflux for about 1 h. A pale-yellow solid was obtained after leaving the solvent to evaporate. Crystals of good quality and suitable for single-crystal X-ray diffraction were grown from its acetonitrile solution. M.pt 457 (1) K.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. All H-atoms were positioned at geometrically idealized positions with C—H distances of 0.93 Å, and with U_iso(H) = 1.2U_eq(C). The Br atom was disordered over two positions [site occupancy for the minor component = 0.48 (4)].

Results and discussion top

In the present work, the structure of the 2,4,6-trinitrophenyl 4-bromobenzoate (I) has been determined and is part of a series of picryl substituted-esters compounds that have been synthesized in our research group. The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles are normal and are comparable with those reported for related compounds (Moreno-Fuquen et al., 2013). The title molecule is twisted: the benzene rings form a dihedral angle of 80.90 (9)°. The central ester moiety C1—O7—C7(O8)—C8 is effectively planar (r.m.s. deviation of all non-hydrogen atoms = 0.0122 Å) and it forms angles of 3.2 (3) and 82.84 (10)° with the benzoate and the picryl rings, respectively. The nitro groups form dihedral angles with the attached benzene ring of 3.7 (3), 8.8 (3) and 20.8 (2)° for O1—N1—O2, O3—N2—O4 and O5—N3—O6, respectively.

In the crystal, in a first substructure, the molecules are intertwined by weak C—H···O interactions, forming helical chains along [100]. The C10 atom of the benzoate ring acts as a hydrogen-bond donor to atom O2 at (-x+1, +y+1/2, -z+3/2). Growth in this direction is reinforced by the weak C5—H5···O8 interaction, in which the C5 atom of the picryl ring acts as hydrogen-bond donor to carbonyl atom O8 at (-x+2,+y+1/2, -z+3/2). In this same substructure the C12 atom in the molecule acts as a hydrogen-bond donor to nitro-O1 atom at (-x+1, -y, -z+1), whose interaction contributes to the growth of the crystal along [010]. The combination of these three contacts generate R²₂(20) and R⁶₆(38) rings along [100] (Fig. 2). In a second substructure shown in Fig. 3, it can be observed the formation of a chain of molecules through the weak C3—H3···O6 interactions. The C3 atom acts as hydrogen-bond donor to O6 atom of the nitro group in the molecule at (x, -y+1/2, +z+1/2), forming C(7) chains along [001]. Thus, the crystal system is a three-dimensional structure, sustained via C—H···O interactions (see Table 1; Nardelli, 1995). No Br···Br interactions are found in the crystal structure.

Related literature top

For similar esters, see: Moreno-Fuquen et al. (2013). For hydrogen bonding, see: Nardelli (1995).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. Molecular conformation and atom numbering scheme for the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I), showing the formation of helical chains which running along [100] and [010]. Symmetry codes: (i) -x+1, +y+1/2, -z+3/2; (ii) -x+1, -y, -z+1; (iii) -x+2, +y+1/2, -z+3/2.
	Fig. 3. Part of the crystal structure of (I), showing the formation of chains of molecules which running along [001]. Symmetry code: (iv) x, -y+1/2,+z+1/2.

2,4,6-Trinitrophenyl 4-bromobenzoate top

Crystal data top

C₁₃H₆BrN₃O₈	F(000) = 816
M_r = 412.12	D_x = 1.827 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 457(1) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.8409 (5) Å	Cell parameters from 6103 reflections
b = 10.0152 (7) Å	θ = 2.9–27.5°
c = 13.9777 (7) Å	µ = 2.80 mm⁻¹
β = 99.246 (3)°	T = 295 K
V = 1497.89 (15) Å³	Block, pale yellow
Z = 4	0.34 × 0.13 × 0.11 mm

Data collection top

Nonius KappaCCD diffractometer	3340 independent reflections
Radiation source: fine-focus sealed tube	2092 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
CCD rotation images, thick slices scans	θ_max = 27.6°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→13
T_min = 0.668, T_max = 0.753	k = −11→13
10473 measured reflections	l = −18→16

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0632P)² + 0.3604P] where P = (F_o² + 2F_c²)/3
3340 reflections	(Δ/σ)_max < 0.001
236 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₃H₆BrN₃O₈	V = 1497.89 (15) Å³
M_r = 412.12	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8409 (5) Å	µ = 2.80 mm⁻¹
b = 10.0152 (7) Å	T = 295 K
c = 13.9777 (7) Å	0.34 × 0.13 × 0.11 mm
β = 99.246 (3)°

Data collection top

Nonius KappaCCD diffractometer	3340 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2092 reflections with I > 2σ(I)
T_min = 0.668, T_max = 0.753	R_int = 0.060
10473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
3340 reflections	Δρ_min = −0.50 e Å⁻³
236 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Br1A	0.3092 (13)	0.2505 (17)	0.2655 (8)	0.100 (2)	0.48 (4)
Br1B	0.2896 (6)	0.2267 (6)	0.2775 (5)	0.0781 (10)	0.52 (4)
O7	0.70356 (18)	0.2879 (2)	0.69502 (15)	0.0547 (5)
O8	0.8026 (2)	0.1287 (3)	0.62476 (17)	0.0831 (8)
N1	0.6967 (3)	0.0905 (3)	0.8454 (2)	0.0606 (7)
C13	0.6090 (3)	0.1222 (3)	0.4631 (2)	0.0517 (7)
H13	0.6728	0.0598	0.4646	0.062*
N3	0.9026 (2)	0.4791 (3)	0.7109 (2)	0.0630 (7)
O6	0.8478 (3)	0.4642 (3)	0.62908 (16)	0.0870 (8)
C6	0.8938 (3)	0.3763 (3)	0.78448 (19)	0.0475 (6)
O1	0.6128 (3)	0.0871 (3)	0.7775 (2)	0.0940 (9)
C8	0.6080 (3)	0.2073 (3)	0.5414 (2)	0.0478 (7)
C5	0.9857 (3)	0.3788 (3)	0.8661 (2)	0.0515 (7)
H5	1.0486	0.4429	0.8731	0.062*
O2	0.7002 (3)	0.0195 (3)	0.9141 (2)	0.1052 (11)
O4	1.1481 (3)	0.3782 (3)	1.0350 (2)	0.0979 (10)
O5	0.9625 (3)	0.5792 (3)	0.7381 (2)	0.1012 (10)
C12	0.5168 (3)	0.1292 (3)	0.3836 (2)	0.0579 (8)
H12	0.5183	0.0729	0.3308	0.070*
C7	0.7141 (3)	0.1995 (3)	0.6211 (2)	0.0525 (7)
C3	0.8886 (3)	0.1888 (3)	0.9281 (2)	0.0496 (7)
H3	0.8878	0.1250	0.9764	0.060*
C4	0.9808 (3)	0.2838 (3)	0.9359 (2)	0.0501 (7)
N2	1.0775 (3)	0.2846 (3)	1.0231 (2)	0.0663 (8)
C1	0.7978 (2)	0.2826 (3)	0.77309 (18)	0.0456 (6)
O3	1.0787 (3)	0.1913 (3)	1.0790 (2)	0.1036 (10)
C2	0.7973 (3)	0.1898 (3)	0.84741 (19)	0.0472 (6)
C9	0.5104 (3)	0.2978 (4)	0.5407 (2)	0.0615 (8)
H9	0.5080	0.3537	0.5935	0.074*
C10	0.4172 (3)	0.3040 (4)	0.4609 (3)	0.0714 (10)
H10	0.3515	0.3640	0.4597	0.086*
C11	0.4220 (3)	0.2211 (3)	0.3833 (2)	0.0621 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.086 (3)	0.139 (4)	0.0585 (17)	0.037 (2)	−0.0375 (19)	−0.026 (2)
Br1B	0.0657 (12)	0.087 (2)	0.0686 (17)	0.0096 (11)	−0.0283 (9)	−0.0107 (9)
O7	0.0510 (11)	0.0685 (13)	0.0392 (10)	0.0097 (9)	−0.0088 (8)	−0.0089 (10)
O8	0.0712 (15)	0.104 (2)	0.0630 (14)	0.0406 (14)	−0.0233 (11)	−0.0294 (14)
N1	0.0652 (16)	0.0599 (16)	0.0532 (15)	−0.0119 (13)	−0.0010 (13)	−0.0088 (13)
C13	0.0490 (15)	0.0539 (17)	0.0486 (15)	0.0026 (12)	−0.0027 (13)	−0.0045 (14)
N3	0.0569 (15)	0.0748 (19)	0.0550 (16)	0.0002 (14)	0.0021 (12)	0.0124 (14)
O6	0.124 (2)	0.0891 (19)	0.0434 (13)	0.0033 (16)	0.0012 (14)	0.0082 (13)
C6	0.0503 (15)	0.0517 (16)	0.0384 (14)	0.0037 (12)	0.0008 (11)	0.0024 (13)
O1	0.0849 (17)	0.095 (2)	0.0896 (19)	−0.0353 (15)	−0.0253 (15)	0.0026 (16)
C8	0.0465 (14)	0.0545 (17)	0.0392 (14)	0.0024 (12)	−0.0029 (12)	−0.0010 (13)
C5	0.0476 (15)	0.0572 (17)	0.0470 (16)	−0.0027 (12)	−0.0004 (12)	−0.0035 (14)
O2	0.120 (2)	0.112 (2)	0.0748 (18)	−0.060 (2)	−0.0083 (17)	0.0232 (17)
O4	0.0877 (18)	0.113 (2)	0.0782 (18)	−0.0375 (17)	−0.0326 (14)	0.0049 (16)
O5	0.0850 (18)	0.102 (2)	0.103 (2)	−0.0365 (16)	−0.0261 (16)	0.0474 (18)
C12	0.0588 (17)	0.0632 (19)	0.0469 (16)	0.0008 (14)	−0.0062 (13)	−0.0123 (15)
C7	0.0522 (16)	0.0636 (19)	0.0378 (15)	0.0066 (14)	−0.0042 (12)	−0.0073 (14)
C3	0.0576 (16)	0.0526 (17)	0.0361 (14)	0.0007 (13)	−0.0002 (12)	−0.0006 (13)
C4	0.0478 (15)	0.0589 (18)	0.0392 (15)	0.0009 (13)	−0.0061 (12)	−0.0030 (14)
N2	0.0621 (16)	0.080 (2)	0.0495 (15)	−0.0071 (15)	−0.0141 (13)	0.0007 (15)
C1	0.0439 (14)	0.0572 (17)	0.0326 (13)	0.0046 (12)	−0.0036 (11)	−0.0070 (12)
O3	0.105 (2)	0.112 (2)	0.0749 (18)	−0.0181 (18)	−0.0409 (17)	0.0316 (18)
C2	0.0508 (15)	0.0494 (16)	0.0394 (14)	−0.0040 (12)	0.0011 (12)	−0.0071 (13)
C9	0.0556 (17)	0.075 (2)	0.0479 (17)	0.0163 (16)	−0.0087 (14)	−0.0156 (16)
C10	0.0628 (19)	0.086 (3)	0.058 (2)	0.0252 (18)	−0.0121 (16)	−0.0195 (19)
C11	0.0549 (17)	0.075 (2)	0.0489 (17)	0.0057 (15)	−0.0149 (14)	−0.0107 (16)

Geometric parameters (Å, º) top

Br1A—C11	1.909 (7)	C8—C7	1.469 (4)
Br1B—C11	1.889 (6)	C5—C4	1.371 (4)
O7—C1	1.371 (3)	C5—H5	0.9300
O7—C7	1.379 (4)	O4—N2	1.205 (4)
O8—C7	1.188 (4)	C12—C11	1.380 (5)
N1—O2	1.191 (4)	C12—H12	0.9300
N1—O1	1.205 (3)	C3—C4	1.372 (4)
N1—C2	1.473 (4)	C3—C2	1.376 (4)
C13—C12	1.371 (4)	C3—H3	0.9300
C13—C8	1.389 (4)	C4—N2	1.474 (4)
C13—H13	0.9300	N2—O3	1.217 (4)
N3—O6	1.210 (3)	C1—C2	1.394 (4)
N3—O5	1.222 (4)	C9—C10	1.381 (4)
N3—C6	1.469 (4)	C9—H9	0.9300
C6—C5	1.389 (4)	C10—C11	1.374 (5)
C6—C1	1.392 (4)	C10—H10	0.9300
C8—C9	1.392 (4)

C1—O7—C7	115.5 (2)	C4—C3—H3	120.7
O2—N1—O1	122.8 (3)	C2—C3—H3	120.7
O2—N1—C2	117.4 (3)	C5—C4—C3	122.4 (3)
O1—N1—C2	119.8 (3)	C5—C4—N2	118.8 (3)
C12—C13—C8	120.7 (3)	C3—C4—N2	118.8 (3)
C12—C13—H13	119.6	O4—N2—O3	124.6 (3)
C8—C13—H13	119.6	O4—N2—C4	118.0 (3)
O6—N3—O5	123.5 (3)	O3—N2—C4	117.4 (3)
O6—N3—C6	119.9 (3)	O7—C1—C6	120.8 (2)
O5—N3—C6	116.6 (3)	O7—C1—C2	121.9 (2)
C5—C6—C1	122.1 (3)	C6—C1—C2	117.2 (2)
C5—C6—N3	116.4 (3)	C3—C2—C1	121.9 (3)
C1—C6—N3	121.6 (2)	C3—C2—N1	116.3 (3)
C13—C8—C9	119.7 (3)	C1—C2—N1	121.8 (2)
C13—C8—C7	117.5 (2)	C10—C9—C8	119.5 (3)
C9—C8—C7	122.8 (3)	C10—C9—H9	120.3
C4—C5—C6	117.9 (3)	C8—C9—H9	120.3
C4—C5—H5	121.0	C11—C10—C9	119.6 (3)
C6—C5—H5	121.0	C11—C10—H10	120.2
C13—C12—C11	118.8 (3)	C9—C10—H10	120.2
C13—C12—H12	120.6	C10—C11—C12	121.6 (3)
C11—C12—H12	120.6	C10—C11—Br1B	118.7 (3)
O8—C7—O7	121.0 (3)	C12—C11—Br1B	119.6 (3)
O8—C7—C8	126.3 (3)	C10—C11—Br1A	119.2 (3)
O7—C7—C8	112.7 (2)	C12—C11—Br1A	118.6 (3)
C4—C3—C2	118.6 (3)

O6—N3—C6—C5	161.2 (3)	C7—O7—C1—C2	−83.5 (3)
O5—N3—C6—C5	−21.7 (4)	C5—C6—C1—O7	175.6 (3)
O6—N3—C6—C1	−19.3 (4)	N3—C6—C1—O7	−3.9 (4)
O5—N3—C6—C1	157.8 (3)	C5—C6—C1—C2	−0.1 (4)
C12—C13—C8—C9	2.1 (5)	N3—C6—C1—C2	−179.6 (3)
C12—C13—C8—C7	−176.2 (3)	C4—C3—C2—C1	1.3 (4)
C1—C6—C5—C4	1.0 (4)	C4—C3—C2—N1	−176.6 (3)
N3—C6—C5—C4	−179.6 (3)	O7—C1—C2—C3	−176.7 (2)
C8—C13—C12—C11	−0.9 (5)	C6—C1—C2—C3	−1.0 (4)
C1—O7—C7—O8	−3.2 (5)	O7—C1—C2—N1	1.2 (4)
C1—O7—C7—C8	178.0 (2)	C6—C1—C2—N1	176.8 (3)
C13—C8—C7—O8	1.5 (5)	O2—N1—C2—C3	1.7 (4)
C9—C8—C7—O8	−176.8 (4)	O1—N1—C2—C3	179.0 (3)
C13—C8—C7—O7	−179.9 (3)	O2—N1—C2—C1	−176.2 (3)
C9—C8—C7—O7	1.8 (4)	O1—N1—C2—C1	1.1 (4)
C6—C5—C4—C3	−0.7 (4)	C13—C8—C9—C10	−1.6 (5)
C6—C5—C4—N2	180.0 (3)	C7—C8—C9—C10	176.7 (3)
C2—C3—C4—C5	−0.5 (5)	C8—C9—C10—C11	−0.1 (6)
C2—C3—C4—N2	178.9 (3)	C9—C10—C11—C12	1.3 (6)
C5—C4—N2—O4	8.8 (5)	C9—C10—C11—Br1B	177.4 (4)
C3—C4—N2—O4	−170.6 (3)	C9—C10—C11—Br1A	−169.6 (9)
C5—C4—N2—O3	−172.5 (3)	C13—C12—C11—C10	−0.8 (6)
C3—C4—N2—O3	8.1 (5)	C13—C12—C11—Br1B	−176.9 (3)
C7—O7—C1—C6	101.0 (3)	C13—C12—C11—Br1A	170.2 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.48	3.169 (4)	131
C12—H12···O1ⁱⁱ	0.93	2.49	3.273 (4)	142
C5—H5···O8ⁱⁱⁱ	0.93	2.46	3.384 (4)	173
C3—H3···O6^iv	0.93	2.42	3.291 (4)	157

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+2, y+1/2, −z+3/2; (iv) x, −y+1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.93	2.48	3.169 (4)	131
C12—H12···O1ⁱⁱ	0.93	2.49	3.273 (4)	142
C5—H5···O8ⁱⁱⁱ	0.93	2.46	3.384 (4)	173
C3—H3···O6^iv	0.93	2.42	3.291 (4)	157

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+2, y+1/2, −z+3/2; (iv) x, −y+1/2, z+1/2.

Acknowledgements

RMF thanks the Universidad del Valle, Colombia, for partial financial support.

References

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