Crystal structure and Hirshfeld surface analysis of 4-bromo­anilinium nitrate

Anbarasan, R.; Eniya, P.; Kalyana Sundar, J.; Menberu Woldemariam, M.

doi:10.1107/S2056989020006945

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 76| Part 6| June 2020| Pages 973-976

https://doi.org/10.1107/S2056989020006945

Open

access

Crystal structure and Hirshfeld surface analysis of 4-bromoanilinium nitrate

Radhakrishnan Anbarasan,^a Palaniyasan Eniya,^a Jeyaperumal Kalyana Sundar ^a and Menberu Mengesha Woldemariam ^b ^*

^aMaterials Science Laboratory, Department of Physics, Periyar University, Salem, India, and ^bDepartment of Physics, Jimma University, Jimma, Ethiopia
^*Correspondence e-mail: menberu.mengesha@ju.edu.et

Edited by J. T. Mague, Tulane University, USA (Received 19 February 2020; accepted 22 May 2020; online 29 May 2020)

The title compound C₄H₇BrN⁺·NO₃⁻ crystallizes in the monoclinic crystal system with space group P2₁/c. In the crystal, π-π stacking interactions and strong N—H⋯O and C—H⋯O hydrogen bonds link the cations and anions into layers parallel to the bc plane. The O⋯H/H⋯O interactions between the cation and anion are the major factor determining the crystal packing.

Keywords: crystal structure; Hirshfeld surface; hydrogen bonds; aniline.

CCDC reference: 1909800

1. Chemical context

In recent years, halogenated anilines and their derivatives have been studied extensively for applications as anticorrosives, antibacterials and in non-linear optical systems (Glidewell et al., 2005 ; Vivek et al., 2014 ). The simplest halogenated aniline readily forms metal/non-metal complexes (Hartmann et al., 1990 ). Strong hydrogen bonding, non-covalent bonding and π–π stacking interactions are prominent in the supramolecular arrangements of this molecule. Here, we report the crystal structure of 4-bromoanilinium nitrate, a salt complex whose structure is closely related to its 4-iodo analogue regarding the hydrogen-bond networks and π–π interactions (Fu et al., 2010 ) although having significantly different unit-cell parameters.

2. Structural commentary

The asymmetric unit consists of two 4-bromoanilinium cations and two nitrate anions which are associated through N1—H10⋯O4ⁱⁱ, N2—H13⋯O3^iv and a bifurcated N1—H9⋯O2ⁱ/N1—H9⋯O3ⁱ hydrogen bonds (Fig. 1). This motif generates a van der Waals contact (O3⋯O6) of 2.980 (4) Å between the two nitrate ions. The phenyl rings in the independent cations extend in the same direction from the pair of anions with a dihedral angle of only 4.8 (2)° between their mean planes and participate in a π–π stacking interaction with a centroid⋯centroid distance of 3.932 (2) Å. Meanwhile, one cation is rotated with respect to the other so that the Br1—C2⋯C10—Br2 torsion angle is 50.4 (su?)°.

Figure 1
The asymmetric unit with labelling scheme and 50% probability ellipsoids. N—H⋯O hydrogen bonds and π-stacking interactions are shown, respectively, by blue and orange dashed lines.

3. Supramolecular features

In the crystal, the anions are arranged in coarsely corrugated layers parallel to the bc plane with the hydrogen-bonded cations protruding from each face in an alternating fashion (Fig. 2). The cations containing Br1 are perpendicular to the layers and make close Br1⋯O5 contacts of 3.229 (5) Å (0.14 Å less than the sum of the van der Waals radii) with nitrate ions in adjacent layers (Fig. 2, Table 1).

Table 1
ydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H9⋯O2ⁱ	0.89	2.19	2.930 (5)	140
N1—H9⋯O3ⁱ	0.89	2.15	3.002 (5)	160
N1—H10⋯O4ⁱ	0.89	2.08	2.957 (4)	167
N1—H11⋯O2ⁱⁱ	0.89	1.91	2.773 (4)	162
N2—H12⋯O1ⁱ	0.89	2.59	3.356 (6)	145
N2—H12⋯O6ⁱ	0.89	2.11	2.827 (5)	137
N2—H12⋯O1ⁱⁱⁱ	0.89	2.59	3.158 (5)	122
N2—H13⋯O3^iv	0.89	2.12	2.774 (5)	130
N2—H13⋯O6^iv	0.89	2.55	3.345 (5)	149
N2—H14⋯O4ⁱⁱⁱ	0.89	2.19	2.831 (5)	129
C4—H3⋯O1ⁱⁱⁱ	0.93	2.41	3.129 (5)	134
C12—H8⋯O3ⁱ	0.93	2.59	3.410 (5)	147
C12—H8⋯O6ⁱ	0.93	2.58	3.1943 (3)	124
Symmetry codes: (i) x+1, y, z; (ii) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z; (iv) -x+1, -y+1, -z+1.

Figure 2
Packing viewed along the c-axis direction showing a portion of two coarsely corrugated layers of anions with the cations extending alternately from each side. The N—H⋯O and C—H⋯O hydrogen bonds are shown, respectively, by blue and black dashed lines. The Br⋯O interactions are shown by green dashed lines.

4. Hirshfeld surface analysis

The intermolecular interactions were investigated quantitatively and visualized with Crystal Explorer 3.1 (Wolff et al., 2012 ; Spackman et al., 2009 ). The d_norm, curvedness and 2D fingerprint plots are depicted in Figs. 3–5 , respectively. The red spots on the Hirshfeld surface represent N—H⋯O contacts (Br⋯O contacts are not visible as red spots) while the blue regions correspond to weak interactions such as C—H⋯O contacts. The two triangles in the curvedness surface clearly illustrate the π–π stacking interactions. The O⋯H/H⋯O (51.4%) interactions are the major factor in the crystal packing with H⋯H (15.5%) interactions representing the next highest contribution. The percentage contributions of other weak interactions are: H⋯Br/Br⋯H (10.3%), C⋯H/H⋯C (9.2%), O⋯Br/Br⋯O (4.1%), Br⋯Br (2.7%), N⋯H/H⋯N (1.7%), O⋯O (1.6%), C⋯C (1.5%), C⋯O/O⋯C (0.8%), N⋯Br/Br⋯N (0.4), C⋯Br/Br⋯C (0.4%), N⋯O/O⋯N (0.3%) and N⋯C/C⋯N (0.1%).

Figure 3
Hirshfeld surface plotted over d_norm.

Figure 4
Curvedness surface of the title compound showing the π–π stacking.

Figure 5
Fingerprint plots for the title compound

4.1. Database survey

A search of the Cambridge Structural Database (CSD version 5.41, last update April 2020; Groom et al., 2016 ) for the 4-bromoanilinium cation gave 22 hits excluding metal complexes. Among these, 13 structures have this cation combined with various acid anions including [PO₂(OH)₂]⁻ (EBEFAV; Yoshii et al., 2015 ; UGISEI; Zhang et al., 2001 ; UGISEI01; Yoshii et al., 2015), [HC₂O₄]⁻ (ROBXOY; Radhakrishnan & Jeyaperumal, 2019 ), [C₄H₅O₆]⁻ (ROPTEX; Yoshii et al., 2014 ) and [p-CH₃C₆H₄SO₃]⁻ (VUCBAY; Sivakumar et al., 2015 ). Two more have amide anions [N(SO₂R)₂]⁻ [R = Me (TAJWOT; Jones et al., 2016 ), 4-BrC₆H₄ (DOHSOJ; Lozano et al., 2008 )]. The remainder have inorganic anions such as [SiF₆]²⁻ (PBANIL; Denne et al., 1971 ), [PF₆]⁻ (TUPWUX; Yang & Fu, 2010 ) and chloride (TAWRAL; Portalone, 2005 ). Additionally, there is an unpublished structure of the title compound (ROCNOP; Anbarasan & Sundar, 2019 ) of comparable quality to the present study but without the additional investigations presented here.

5. Synthesis and crystallization

The title salt was synthesized by dissolving analytical grade 4-bromoaniline and nitric acid in a 1:1 stoichiometric ratio in methanol. The solution was stirred continuously for 2 h. Slow evaporation of this solution at room temperature yielded transparent colourless single crystals of the product.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The H atoms were positioned geometrically and refined using a riding model: C—H = 0.93 Å with U_iso(H) = 1.2U_eq(C) and N—H = 0.86 Å with U_iso(H) = 1.2U_eq(N). Reflection (100) was obscured by the beam stop and was omitted during the final refinement cycle.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₇BrN⁺·NO₃⁻
M_r	235.04
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.7123 (8), 23.4964 (19), 7.6264 (6)
β (°)	97.052 (4)
V (Å³)	1727.2 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	4.73
Crystal size (mm)	0.42 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.374, 0.567
No. of measured, independent and observed [I > 2σ(I)] reflections	16821, 4609, 2355
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.183, 1.02
No. of reflections	4609
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.84
Computer programs: APEX2 and SAINT (Bruker, 2004 ), SHELXT (Sheldrick, 2015a ), SHELXL2017 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), PLATON (Spek, 2020 ), Mercury (Macrae et al., 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1909800

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989020006945/mw2155sup1.cif

Supporting information file. DOI: https://doi.org/10.1107/S2056989020006945/mw2155Isup2.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012), PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and publCIF (Westrip, 2010).

p-Bromoanilinium nitrate top

Crystal data top

C₆H₇BrN⁺·NO₃⁻	F(000) = 928
M_r = 235.04	D_x = 1.808 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4609 reflections
a = 9.7123 (8) Å	θ = 2.6–29.1°
b = 23.4964 (19) Å	µ = 4.73 mm⁻¹
c = 7.6264 (6) Å	T = 293 K
β = 97.052 (4)°	Needle, colorless
V = 1727.2 (2) Å³	0.42 × 0.18 × 0.12 mm
Z = 8

Data collection top

Bruker SMART APEXII CCD diffractometer	2355 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.058
ω and φ scan	θ_max = 29.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→11
T_min = 0.374, T_max = 0.567	k = −29→32
16821 measured reflections	l = −8→10
4609 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.059	w = 1/[σ²(F_o²) + (0.0927P)² + 0.2455P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.183	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.68 e Å⁻³
4609 reflections	Δρ_min = −0.84 e Å⁻³
218 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b)
0 restraints	Extinction coefficient: 0.0181 (17)

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.

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

	x	y	z	U_iso*/U_eq
N1	1.0463 (4)	0.32338 (12)	0.2075 (4)	0.0513 (8)
H10	1.083534	0.351431	0.150589	0.077*
H9	1.063697	0.329131	0.323465	0.077*
H11	1.082988	0.290327	0.180092	0.077*
N2	0.8383 (4)	0.52952 (13)	0.2737 (5)	0.0571 (9)
H14	0.798745	0.556374	0.202137	0.086*
H13	0.880154	0.545557	0.371772	0.086*
H12	0.900523	0.510739	0.219564	0.086*
N3	0.0880 (3)	0.32409 (14)	0.6621 (5)	0.0481 (8)
N4	0.1286 (3)	0.46630 (13)	0.1594 (5)	0.0531 (9)
O2	0.1085 (4)	0.28155 (12)	0.5705 (5)	0.0762 (10)
O3	0.0604 (4)	0.36877 (12)	0.5772 (5)	0.0891 (12)
O4	0.1736 (3)	0.42637 (11)	0.0733 (4)	0.0613 (8)
O5	0.0995 (5)	0.32142 (18)	0.8212 (5)	0.0941 (12)
O6	0.0681 (3)	0.45499 (12)	0.2920 (4)	0.0656 (8)
O1	0.1429 (4)	0.51579 (11)	0.1125 (5)	0.0766 (10)
C1	0.6768 (5)	0.28047 (18)	0.1770 (6)	0.0632 (12)
H1	0.622297	0.253605	0.225586	0.076*
C2	0.6166 (5)	0.31894 (18)	0.0536 (5)	0.0549 (11)
C3	0.6968 (5)	0.35869 (17)	−0.0173 (6)	0.0611 (12)
H2	0.655897	0.384689	−0.099684	0.073*
C4	0.8371 (5)	0.36032 (15)	0.0328 (5)	0.0539 (11)
H3	0.891543	0.387124	−0.016287	0.065*
C5	0.8970 (4)	0.32216 (14)	0.1558 (5)	0.0449 (9)
C6	0.8179 (5)	0.28202 (17)	0.2278 (6)	0.0576 (11)
H4	0.859217	0.256095	0.310167	0.069*
C7	0.7319 (4)	0.48981 (15)	0.3193 (5)	0.0466 (9)
C8	0.5964 (5)	0.49725 (19)	0.2493 (6)	0.0638 (12)
H5	0.571499	0.527478	0.173184	0.077*
C9	0.4971 (5)	0.4596 (2)	0.2925 (7)	0.0779 (14)
H6	0.40465	0.463954	0.245794	0.094*
C10	0.5363 (5)	0.4159 (2)	0.4046 (6)	0.0640 (12)
C11	0.6718 (5)	0.40804 (19)	0.4725 (6)	0.0607 (11)
H7	0.696645	0.377689	0.548105	0.073*
C12	0.7710 (4)	0.44517 (19)	0.4285 (5)	0.0562 (11)
H8	0.863752	0.439985	0.472598	0.067*
Br1	0.42315 (6)	0.31590 (3)	−0.02005 (7)	0.0826 (3)
Br2	0.40126 (7)	0.36433 (3)	0.47100 (8)	0.1017 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.070 (2)	0.0398 (16)	0.0435 (19)	−0.0049 (16)	0.0034 (17)	−0.0031 (14)
N2	0.056 (2)	0.0473 (19)	0.065 (2)	0.0020 (16)	−0.0038 (17)	−0.0121 (17)
N3	0.0476 (19)	0.0412 (18)	0.054 (2)	−0.0059 (14)	0.0019 (16)	0.0022 (17)
N4	0.0414 (19)	0.0379 (18)	0.075 (3)	−0.0029 (15)	−0.0123 (17)	0.0051 (18)
O2	0.113 (3)	0.0430 (17)	0.072 (2)	−0.0017 (16)	0.010 (2)	−0.0044 (15)
O3	0.119 (3)	0.0353 (16)	0.103 (3)	0.0007 (17)	−0.026 (2)	0.0073 (17)
O4	0.0609 (19)	0.0433 (15)	0.079 (2)	0.0103 (14)	0.0043 (15)	−0.0019 (14)
O5	0.095 (3)	0.140 (3)	0.047 (2)	0.007 (2)	0.0077 (19)	−0.007 (2)
O6	0.067 (2)	0.0597 (18)	0.072 (2)	−0.0003 (15)	0.0160 (17)	0.0087 (16)
O1	0.097 (3)	0.0328 (15)	0.099 (3)	−0.0081 (15)	0.007 (2)	0.0106 (16)
C1	0.068 (3)	0.065 (3)	0.058 (3)	−0.006 (2)	0.012 (2)	0.015 (2)
C2	0.063 (3)	0.060 (3)	0.042 (2)	0.008 (2)	0.0049 (19)	−0.007 (2)
C3	0.084 (4)	0.051 (2)	0.048 (3)	0.013 (2)	0.006 (2)	0.010 (2)
C4	0.073 (3)	0.036 (2)	0.053 (3)	−0.0020 (19)	0.007 (2)	0.0068 (18)
C5	0.062 (3)	0.0344 (18)	0.038 (2)	0.0014 (17)	0.0056 (18)	−0.0034 (16)
C6	0.070 (3)	0.052 (2)	0.050 (2)	−0.002 (2)	0.004 (2)	0.0139 (19)
C7	0.047 (2)	0.047 (2)	0.044 (2)	0.0037 (18)	0.0029 (17)	−0.0105 (18)
C8	0.054 (3)	0.070 (3)	0.066 (3)	0.013 (2)	0.002 (2)	0.007 (2)
C9	0.042 (3)	0.118 (4)	0.071 (3)	0.004 (3)	−0.005 (2)	0.013 (3)
C10	0.060 (3)	0.078 (3)	0.056 (3)	−0.013 (2)	0.014 (2)	−0.007 (2)
C11	0.063 (3)	0.066 (3)	0.054 (3)	−0.002 (2)	0.008 (2)	0.007 (2)
C12	0.048 (2)	0.065 (3)	0.053 (3)	0.009 (2)	−0.005 (2)	−0.001 (2)
Br1	0.0635 (4)	0.1164 (5)	0.0676 (4)	0.0127 (3)	0.0060 (3)	−0.0013 (3)
Br2	0.0876 (5)	0.1390 (6)	0.0825 (5)	−0.0422 (4)	0.0262 (3)	0.0036 (3)

Geometric parameters (Å, º) top

N1—C5	1.456 (5)	C2—Br1	1.895 (5)
N1—H10	0.89	C3—C4	1.369 (6)
N1—H9	0.89	C3—H2	0.93
N1—H11	0.89	C4—C5	1.375 (5)
N2—C7	1.465 (5)	C4—H3	0.93
N2—H14	0.89	C5—C6	1.373 (6)
N2—H13	0.89	C6—H4	0.93
N2—H12	0.89	C7—C12	1.364 (6)
N3—O5	1.207 (5)	C7—C8	1.370 (6)
N3—O3	1.245 (4)	C8—C9	1.379 (7)
N3—O2	1.249 (4)	C8—H5	0.93
N4—O1	1.229 (4)	C9—C10	1.360 (7)
N4—O4	1.254 (4)	C9—H6	0.93
N4—O6	1.258 (4)	C10—C11	1.366 (6)
C1—C6	1.378 (7)	C10—Br2	1.900 (4)
C1—C2	1.382 (6)	C11—C12	1.372 (6)
C1—H1	0.93	C11—H7	0.93
C2—C3	1.369 (6)	C12—H8	0.93

C5—N1—H10	109.5	C3—C4—C5	119.7 (4)
C5—N1—H9	109.5	C3—C4—H3	120.2
H10—N1—H9	109.5	C5—C4—H3	120.2
C5—N1—H11	109.5	C6—C5—C4	120.7 (4)
H10—N1—H11	109.5	C6—C5—N1	119.5 (3)
H9—N1—H11	109.5	C4—C5—N1	119.8 (4)
C7—N2—H14	109.5	C5—C6—C1	119.4 (4)
C7—N2—H13	109.5	C5—C6—H4	120.3
H14—N2—H13	109.5	C1—C6—H4	120.3
C7—N2—H12	109.5	C12—C7—C8	121.2 (4)
H14—N2—H12	109.5	C12—C7—N2	118.9 (4)
H13—N2—H12	109.5	C8—C7—N2	119.9 (4)
O5—N3—O3	123.7 (4)	C7—C8—C9	119.5 (4)
O5—N3—O2	121.3 (4)	C7—C8—H5	120.3
O3—N3—O2	115.0 (4)	C9—C8—H5	120.3
O1—N4—O4	119.8 (4)	C10—C9—C8	119.0 (4)
O1—N4—O6	120.9 (4)	C10—C9—H6	120.5
O4—N4—O6	119.3 (3)	C8—C9—H6	120.5
C6—C1—C2	119.8 (4)	C9—C10—C11	121.5 (4)
C6—C1—H1	120.1	C9—C10—Br2	120.0 (4)
C2—C1—H1	120.1	C11—C10—Br2	118.5 (4)
C3—C2—C1	120.1 (5)	C10—C11—C12	119.6 (4)
C3—C2—Br1	120.0 (3)	C10—C11—H7	120.2
C1—C2—Br1	119.9 (4)	C12—C11—H7	120.2
C2—C3—C4	120.3 (4)	C7—C12—C11	119.2 (4)
C2—C3—H2	119.9	C7—C12—H8	120.4
C4—C3—H2	119.9	C11—C12—H8	120.4

C6—C1—C2—C3	−0.4 (7)	C12—C7—C8—C9	1.2 (7)
C6—C1—C2—Br1	178.7 (3)	N2—C7—C8—C9	179.8 (4)
C1—C2—C3—C4	0.4 (6)	C7—C8—C9—C10	0.2 (7)
Br1—C2—C3—C4	−178.7 (3)	C8—C9—C10—C11	−1.1 (8)
C2—C3—C4—C5	−0.6 (6)	C8—C9—C10—Br2	178.5 (4)
C3—C4—C5—C6	0.7 (6)	C9—C10—C11—C12	0.6 (7)
C3—C4—C5—N1	179.2 (3)	Br2—C10—C11—C12	−179.1 (3)
C4—C5—C6—C1	−0.6 (6)	C8—C7—C12—C11	−1.8 (6)
N1—C5—C6—C1	−179.2 (4)	N2—C7—C12—C11	179.6 (4)
C2—C1—C6—C5	0.4 (7)	C10—C11—C12—C7	0.9 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H9···O2ⁱ	0.89	2.19	2.930 (5)	140
N1—H9···O3ⁱ	0.89	2.15	3.002 (5)	160
N1—H10···O4ⁱ	0.89	2.08	2.957 (4)	167
N1—H11···O2ⁱⁱ	0.89	1.91	2.773 (4)	162
N2—H12···O1ⁱ	0.89	2.59	3.356 (6)	145
N2—H12···O6ⁱ	0.89	2.11	2.827 (5)	137
N2—H12···O1ⁱⁱⁱ	0.89	2.59	3.158 (5)	122
N2—H13···O3^iv	0.89	2.12	2.774 (5)	130
N2—H13···O6^iv	0.89	2.55	3.345 (5)	149
N2—H14···O4ⁱⁱⁱ	0.89	2.19	2.831 (5)	129
C4—H3···O1ⁱⁱⁱ	0.93	2.41	3.129 (5)	134
C12—H8···O3ⁱ	0.93	2.59	3.410 (5)	147
C12—H8···O6ⁱ	0.93	2.58	3.1943 (3)	124

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

Funding information

RA gratefully acknowledges Periyar University for providing financial support under the University Research Fellowship (URF) scheme.

References

Anbarasan, R. & Sundar, J. K. (2019). CSD Communication (refcode ROCNOP). CCDC, Cambridge, England. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Denne, W. A., Mathieson, A. & Mackay, M. F. (1971). J. Cryst. Mol. Struct. 1, 55–62. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Fu, X. (2010). Acta Cryst. E66, o1326. Google Scholar
Glidewell, C., Low, J. N., Skakle, J. M. S. & Wardell, J. L. (2005). Acta Cryst. C61, o276–o280. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hartmann, J., Dou, S.-Q. & Weiss, A. (1990). Berichte der Bunsengesellschaft für physikalische Chemie, 94, 1110–1121. Google Scholar
Jones, P. G., Blaschette, A. & Moers, O. (2016). CSD Communication (refcode TAJWOT). CCDC, Cambridge, England. Google Scholar
Lozano, V., Freytag, M., Jones, P. G. & Blaschette, A. (2008). Z. Naturforsch. B, 63, 954–962. Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Portalone, G. (2005). Acta Cryst. E61, o3083–o3085. Web of Science CrossRef IUCr Journals Google Scholar
Radhakrishnan, A. & Jeyaperumal, K. S. (2019). CSD Communication (refcode ROBXOY). CCDC, Cambridge, England. Google Scholar
Sheldrick, G. M. (1996). SADABS. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sivakumar, P. K., Kumar, M. K., Kumar, R. M., Chakkaravarthi, G. & Kanagadurai, R. (2015). Acta Cryst. E71, o163–o164. Google Scholar
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Vivek, P. & Murugakoothan, P. (2014). Appl. Phys. A, 115, 1139–1146. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. University of Western Australia. Google Scholar
Yang, Y. & Fu, X. (2010). Acta Cryst. E66, o1430. Google Scholar
Yoshii, Y., Hoshino, N., Takeda, T. & Akutagawa, T. (2015). J. Phys. Chem. C, 119, 20845–20854. Google Scholar
Yoshii, Y., Hoshino, N., Takeda, T., Moritomo, H., Kawamata, J., Nakamura, T. & Akutagawa, T. (2014). Chem. Eur. J. 20, 16279–16285. Google Scholar
Zhang, B.-G., Gou, S.-H., Duan, C.-Y. & You, X.-Z. (2001). Wuhan Dax. Xuebao, Zir. Kex. 47, 425–427. Google Scholar