5-Hydr­oxy-8-nitro-1,4-naphthoquinone

Tan, D.T.-C.; Osman, H.; Kamaruddin, A.H.; Kia, R.; Fun, H.-K.

doi:10.1107/S1600536808021594

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages o1523-o1524

doi:10.1107/S1600536808021594

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5-Hydroxy-8-nitro-1,4-naphthoquinone

Daniel Teoh-Chuan Tan,^a Hasnah Osman,^a ‡ Azlina Harun Kamaruddin,^b Reza Kia ^c and Hoong-Kun Fun ^c ^*

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSchool of Chemical Engineering, Universiti Sains Malaysia, Seri Ampangan, 14300 Nibong Tebal, Penang, Malaysia, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 9 July 2008; accepted 11 July 2008; online 19 July 2008)

The title compound, C₁₀H₅NO₅, features an intramolecular O—H⋯O hydrogen bond, forming a six-membered ring with an S(6) ring motif. The nitro group makes a dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The two rings are almost coplanar, with a dihedral angle of 4.44 (5)°. Short intermolecular distances between the centroids of the six-membered rings [3.7188 (6)–3.8299 (6) Å] indicate the existence of π–π interactions. The interesting features of the crystal structure are the short intermolecular O⋯O and O⋯N interactions. The crystal packing is stabilized by intramolecular O—H⋯O and intermolecular C—H⋯O (×3) hydrogen bonds, and C—H⋯π interactions.

Related literature

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995 ). For values of bond lengths, see Allen et al. (1987 ). For related literature, see, for example: Guingant & Barreto (1987 ); Larsen et al. (1996 ); Krohn et al. (2004 ); Krohn et al. (2004); Cui et al. (2006 ); Anuradha et al. (2006 ).

Experimental

Crystal data

C₁₀H₅NO₅
M_r = 219.15
Monoclinic, P 2₁ /n
a = 8.6809 (2) Å
b = 8.4250 (2) Å
c = 12.1845 (3) Å
β = 93.946 (1)°
V = 889.02 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 100.0 (1) K
0.35 × 0.14 × 0.13 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.900, T_max = 0.982
22792 measured reflections
3028 independent reflections
2493 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.11
3028 reflections
165 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected interatomic and centroid–centroid distances (Å)

Cg1 and Cg2 are the centroids of the C1–C5/C10 and C5–C10 rings, respectively.

Cg1⋯Cg2ⁱ	3.7188 (6)
Cg1⋯Cg2ⁱ	3.8299 (6)
O2⋯O5ⁱ	2.9940 (11)
O5⋯O5ⁱⁱ	3.0367 (11)
O5⋯N1ⁱⁱ	3.0608 (11)
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+2, -y-1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C5/C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.889 (18)	1.769 (19)	2.5695 (10)	148.5 (16)
C2—H2⋯O3ⁱⁱⁱ	0.969 (15)	2.547 (16)	3.1853 (12)	123.4 (12)
C3—H3⋯O5ⁱⁱ	0.970 (15)	2.577 (15)	3.3827 (13)	140.6 (11)
C7—H7⋯O1^iv	0.982 (16)	2.561 (16)	3.1851 (13)	121.4 (12)
C8—H8⋯Cg1^v	0.950 (15)	2.976 (14)	3.6548 (11)	129.5 (11)
Symmetry codes: (ii) -x+2, -y-1, -z+1; (iii) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021594/at2591sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808021594/at2591Isup2.hkl

checkCIF report

Comment top

5-Hydroxy-1,4-naphthoquinone (juglone) and its 5-acetoxy-2-bromo analogue is the essential dienophile in the highly convergent and regiospecific Diels-Alder synthesis of ochromycinone (Guingant & Barreto, 1987; Larsen et al., 1996; Krohn et al., 2004) a type of natural anthraquinone which exhibits remarkable antibiotic and antitumour activities (Krohn et al., 2004; Cui et al., 2006). Our aim is to prepare aromatic ring substituted juglone analogues for the purpose of synthesizing new ochromycinone analogues. The title compound was prepared by the direct nitration of juglone with nickel(II) nitrate. The method outlined previously (Anuradha et al., 2006) predicted a ortho-nitro product. However the product that we obtained is a para-nitro product.

Compound (I), ( Fig. 1), features an intramolecular O—H···O hydrogen bond to form a six-membered ring, producing a S(6) ring motif (Bernstein et al., 1995). The bond lenghts and angles are within the normal ranges (Allen et al., 1987). The two phenyl rings are almost coplanar with the dihedral angle of 4.44 (5)°. The nitro group is not coplanar with the benzene ring and its orientation is indicated by the dihedral angle of 71.66 (5)° with the plane of the benzene ring to which it is bound. The short intermolecular distances between the centroids of six-membered rings [3.7188 (6) - 3.8299 (6) Å] prove existence of π–π interactions (Table 1). The interesting feature of the crystal structure is the short intermolecular O···O and O···N interactions (Table 1). The crystal packing,(Fig. 2), of the compound shows one-dimensional infinite chains along the b axis.The crystal packing is stabilized by the intramolecular O—H···O, intermolecular C—H···O hydrogen bonds, π–π, and C—H···π interactions.

Related literature top

For related literature on hydrogen-bond motifs, see Bernstein et al. (1995). For values of bond lengths, see Allen et al. (1987). For related literature, see, for example: Guingant & Barreto (1987); Larsen et al. (1996); Krohn et al. (2004); Krohn et al. (2004); Cui et al. (2006); Anuradha et al. (2006).

Experimental top

8-Nitro-5-hydroxy-1,4-naphthoquinone was prepared from 5-hydroxy-1,4-naphthoquinone by the protocol outlined by (Anuradha et al., 2006). Single crystals of 8-nitro-5-hydroxy-1,4-naphthoquinone was obtained by slow evaporation of a chloroform solution at 286 K° C.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Intramolecular hydrogen bond is drawn as a dashed line.
	Fig. 2. The crystal packing of (I) shows a one-dimensional infinite chain along the [010] direction when viewed down the a-axis. Intramolecular and intermolecular interactions are drawn as dashed lines.

5-Hydroxy-8-nitro-1,4-naphthoquinone top

Crystal data top

C₁₀H₅NO₅	F(000) = 448
M_r = 219.15	D_x = 1.637 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5257 reflections
a = 8.6809 (2) Å	θ = 2.8–31.8°
b = 8.4250 (2) Å	µ = 0.14 mm⁻¹
c = 12.1845 (3) Å	T = 100 K
β = 93.946 (1)°	Block, brown
V = 889.02 (4) Å³	0.35 × 0.14 × 0.13 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3028 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 31.8°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→12
T_min = 0.901, T_max = 0.982	k = −12→12
22792 measured reflections	l = −18→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0671P)² + 0.1177P] where P = (F_o² + 2F_c²)/3
3028 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 0.50 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₅NO₅	V = 889.02 (4) Å³
M_r = 219.15	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.6809 (2) Å	µ = 0.14 mm⁻¹
b = 8.4250 (2) Å	T = 100 K
c = 12.1845 (3) Å	0.35 × 0.14 × 0.13 mm
β = 93.946 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3028 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2493 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.982	R_int = 0.041
22792 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.50 e Å⁻³
3028 reflections	Δρ_min = −0.23 e Å⁻³
165 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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.

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

	x	y	z	U_iso*/U_eq
O1	0.60929 (9)	0.14448 (9)	0.47684 (6)	0.01684 (17)
O2	0.70729 (9)	0.29533 (9)	0.65117 (6)	0.01718 (17)
O3	1.13635 (9)	−0.14728 (9)	0.74975 (6)	0.01826 (17)
O4	0.97394 (10)	−0.42986 (9)	0.67891 (6)	0.02146 (19)
O5	1.11804 (9)	−0.37894 (9)	0.54429 (6)	0.01912 (18)
N1	1.01058 (10)	−0.34927 (10)	0.60140 (7)	0.01427 (18)
C1	0.71200 (11)	0.03181 (12)	0.50785 (8)	0.01280 (18)
C2	0.71889 (11)	−0.10405 (12)	0.44177 (8)	0.01457 (19)
C3	0.81830 (11)	−0.22605 (12)	0.47321 (8)	0.01431 (19)
C4	0.91370 (11)	−0.21081 (11)	0.56968 (8)	0.01219 (18)
C5	0.91680 (11)	−0.07504 (11)	0.63367 (7)	0.01156 (18)
C6	1.03288 (11)	−0.05166 (12)	0.72840 (8)	0.01326 (19)
C7	1.02414 (12)	0.09636 (13)	0.79222 (8)	0.0172 (2)
C8	0.91880 (12)	0.20847 (12)	0.76649 (8)	0.0168 (2)
C9	0.80517 (11)	0.19086 (12)	0.67159 (8)	0.01387 (19)
C10	0.81225 (11)	0.04769 (11)	0.60319 (8)	0.01189 (18)
H8	0.9139 (16)	0.3051 (18)	0.8063 (12)	0.022 (4)*
H2	0.6513 (17)	−0.1106 (19)	0.3752 (12)	0.025 (4)*
H3	0.8222 (16)	−0.3231 (18)	0.4307 (12)	0.020 (3)*
H7	1.1034 (18)	0.1097 (19)	0.8530 (13)	0.029 (4)*
H1O1	0.620 (2)	0.223 (2)	0.5255 (16)	0.049 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0161 (3)	0.0151 (4)	0.0187 (4)	0.0031 (3)	−0.0031 (3)	0.0017 (3)
O2	0.0197 (4)	0.0144 (4)	0.0176 (3)	0.0040 (3)	0.0029 (3)	0.0005 (3)
O3	0.0190 (4)	0.0170 (4)	0.0179 (3)	0.0025 (3)	−0.0051 (3)	0.0005 (3)
O4	0.0285 (4)	0.0150 (4)	0.0210 (4)	0.0010 (3)	0.0023 (3)	0.0054 (3)
O5	0.0161 (3)	0.0181 (4)	0.0234 (4)	0.0026 (3)	0.0032 (3)	−0.0025 (3)
N1	0.0159 (4)	0.0110 (4)	0.0155 (4)	−0.0001 (3)	−0.0015 (3)	−0.0010 (3)
C1	0.0114 (4)	0.0132 (4)	0.0136 (4)	0.0000 (3)	−0.0003 (3)	0.0021 (3)
C2	0.0142 (4)	0.0156 (5)	0.0135 (4)	−0.0011 (3)	−0.0018 (3)	−0.0004 (3)
C3	0.0152 (4)	0.0138 (4)	0.0138 (4)	−0.0011 (3)	0.0000 (3)	−0.0021 (3)
C4	0.0122 (4)	0.0110 (4)	0.0133 (4)	0.0007 (3)	0.0005 (3)	0.0008 (3)
C5	0.0120 (4)	0.0112 (4)	0.0114 (4)	−0.0010 (3)	0.0002 (3)	−0.0001 (3)
C6	0.0143 (4)	0.0130 (4)	0.0122 (4)	−0.0011 (3)	−0.0012 (3)	0.0005 (3)
C7	0.0203 (5)	0.0157 (5)	0.0150 (4)	−0.0008 (4)	−0.0030 (3)	−0.0026 (4)
C8	0.0204 (5)	0.0144 (5)	0.0153 (4)	−0.0006 (4)	−0.0005 (3)	−0.0035 (3)
C9	0.0155 (4)	0.0123 (4)	0.0141 (4)	−0.0002 (3)	0.0031 (3)	0.0002 (3)
C10	0.0123 (4)	0.0110 (4)	0.0124 (4)	0.0001 (3)	0.0011 (3)	0.0004 (3)

Geometric parameters (Å, º) top

O1—C1	1.3388 (11)	C3—C4	1.3964 (13)
O1—H1O1	0.89 (2)	C3—H3	0.970 (15)
O2—C9	1.2367 (12)	C4—C5	1.3836 (13)
O3—C6	1.2211 (12)	C5—C10	1.4087 (13)
O4—N1	1.2229 (11)	C5—C6	1.4921 (13)
O5—N1	1.2274 (11)	C6—C7	1.4744 (14)
N1—C4	1.4741 (12)	C7—C8	1.3369 (15)
C1—C2	1.4031 (14)	C7—H7	0.982 (16)
C1—C10	1.4091 (13)	C8—C9	1.4748 (14)
C2—C3	1.3793 (14)	C8—H8	0.950 (15)
C2—H2	0.969 (15)	C9—C10	1.4699 (13)

Cg1···Cg2ⁱ	3.7188 (6)	O5···O5ⁱⁱ	3.0367 (11)
Cg1···Cg2ⁱ	3.8299 (6)	O5···N1ⁱⁱ	3.0608 (11)
O2···O5ⁱ	2.9940 (11)

C1—O1—H1O1	107.7 (12)	C4—C5—C6	122.07 (8)
O4—N1—O5	124.96 (9)	C10—C5—C6	119.72 (8)
O4—N1—C4	117.90 (8)	O3—C6—C7	120.63 (9)
O5—N1—C4	117.04 (8)	O3—C6—C5	121.69 (9)
O1—C1—C2	118.06 (8)	C7—C6—C5	117.58 (8)
O1—C1—C10	121.79 (9)	C8—C7—C6	122.22 (9)
C2—C1—C10	120.15 (9)	C8—C7—H7	121.9 (10)
C3—C2—C1	119.94 (9)	C6—C7—H7	115.8 (9)
C3—C2—H2	121.4 (9)	C7—C8—C9	121.51 (9)
C1—C2—H2	118.6 (9)	C7—C8—H8	122.7 (9)
C2—C3—C4	119.26 (9)	C9—C8—H8	115.8 (9)
C2—C3—H3	121.6 (9)	O2—C9—C10	121.66 (9)
C4—C3—H3	119.1 (9)	O2—C9—C8	119.96 (9)
C5—C4—C3	122.53 (9)	C10—C9—C8	118.38 (9)
C5—C4—N1	121.19 (8)	C5—C10—C1	119.86 (9)
C3—C4—N1	116.27 (8)	C5—C10—C9	120.27 (8)
C4—C5—C10	118.10 (8)	C1—C10—C9	119.86 (9)

O1—C1—C2—C3	−177.19 (9)	O3—C6—C7—C8	175.40 (10)
C10—C1—C2—C3	3.41 (15)	C5—C6—C7—C8	−1.17 (15)
C1—C2—C3—C4	−1.45 (15)	C6—C7—C8—C9	−0.45 (16)
C2—C3—C4—C5	−2.37 (15)	C7—C8—C9—O2	178.62 (10)
C2—C3—C4—N1	176.71 (9)	C7—C8—C9—C10	−1.51 (15)
O4—N1—C4—C5	72.88 (12)	C4—C5—C10—C1	−2.00 (14)
O5—N1—C4—C5	−110.47 (10)	C6—C5—C10—C1	174.21 (8)
O4—N1—C4—C3	−106.21 (10)	C4—C5—C10—C9	176.79 (8)
O5—N1—C4—C3	70.44 (11)	C6—C5—C10—C9	−7.00 (14)
C3—C4—C5—C10	4.07 (14)	O1—C1—C10—C5	178.97 (9)
N1—C4—C5—C10	−174.97 (8)	C2—C1—C10—C5	−1.65 (14)
C3—C4—C5—C6	−172.05 (9)	O1—C1—C10—C9	0.17 (14)
N1—C4—C5—C6	8.92 (14)	C2—C1—C10—C9	179.56 (9)
C4—C5—C6—O3	4.45 (15)	O2—C9—C10—C5	−174.82 (9)
C10—C5—C6—O3	−171.60 (9)	C8—C9—C10—C5	5.31 (14)
C4—C5—C6—C7	−179.01 (9)	O2—C9—C10—C1	3.97 (15)
C10—C5—C6—C7	4.94 (13)	C8—C9—C10—C1	−175.90 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.889 (18)	1.769 (19)	2.5695 (10)	148.5 (16)
C2—H2···O3ⁱⁱⁱ	0.969 (15)	2.547 (16)	3.1853 (12)	123.4 (12)
C3—H3···O5ⁱⁱ	0.970 (15)	2.577 (15)	3.3827 (13)	140.6 (11)
C7—H7···O1^iv	0.982 (16)	2.561 (16)	3.1851 (13)	121.4 (12)
C8—H8···Cg1^v	0.950 (15)	2.976 (14)	3.6548 (11)	129.5 (11)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₅NO₅
M_r	219.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	8.6809 (2), 8.4250 (2), 12.1845 (3)
β (°)	93.946 (1)
V (Å³)	889.02 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.14
Crystal size (mm)	0.35 × 0.14 × 0.13

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.901, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	22792, 3028, 2493
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.742

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.11
No. of reflections	3028
No. of parameters	165
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected interatomic distances (Å) top

Cg1···Cg2ⁱ	3.7188 (6)	O5···O5ⁱⁱ	3.0367 (11)
Cg1···Cg2ⁱ	3.8299 (6)	O5···N1ⁱⁱ	3.0608 (11)
O2···O5ⁱ	2.9940 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.889 (18)	1.769 (19)	2.5695 (10)	148.5 (16)
C2—H2···O3ⁱⁱⁱ	0.969 (15)	2.547 (16)	3.1853 (12)	123.4 (12)
C3—H3···O5ⁱⁱ	0.970 (15)	2.577 (15)	3.3827 (13)	140.6 (11)
C7—H7···O1^iv	0.982 (16)	2.561 (16)	3.1851 (13)	121.4 (12)
C8—H8···Cg1^v	0.950 (15)	2.976 (14)	3.6548 (11)	129.5 (11)

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

Footnotes

‡Additional correspondence author, e-mail: ohasnah@usm.my.

Acknowledgements

HO thanks the Malaysian government for the FRGS fund (grant No. 203/PKIMIA/671026). DTCT thanks Universiti Sains Malaysia for financial support. HKF and RK thank the Malaysian government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. RK thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

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