Crystal structure of 1-anilino-5-methyl-1H-1,2,3-triazole-4-carb­oxy­lic acid monohydrate

Moreira, O.B.O.; Freitas, M.C.R.; Souza, K.C.; Jordão, A.K.; Resende, J.A.L.C.

doi:10.1107/S2056989019005711

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 75| Part 6| June 2019| Pages 738-741

https://doi.org/10.1107/S2056989019005711

Open

access

Crystal structure of 1-anilino-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate

Olívia B. O. Moreira,^a Maria Clara R. Freitas,^b Karynne C. Souza,^c Alessandro K. Jordão ^d and Jackson A. L. C. Resende ^c ^*

^aGraduate Program in Chemistry, Department of Chemistry, Universidade Federal de Juiz de Fora, Rua José Lourenço Kelmer, s/n, Juiz de Fora - MG, CEP 36036-330, Brazil, ^bInstituto de Química, Universidade Federal Rural do Rio de Janeiro, BR-465, Km 7, CEP 23.890-000, Seropédica, RJ, Brazil, ^cInstituto de Ciências Exatas e da Terra, Campus Universitário do Araguaia, Universidade Federal do Mato Grosso, Avenida Universitária, 3500, Pontal do Araguaia - MT, CEP 78698-000, Brazil, and ^dDepartamento de Farmácia, Universidade Federal do Rio Grande do Norte, R. Gen. Gustavo Cordeiro de Faria, S/N, Natal - RN, CEP 59012-570, Brazil
^*Correspondence e-mail: jacksonresende@ufmt.br

Edited by J. Ellena, Universidade de Sâo Paulo, Brazil (Received 16 April 2019; accepted 25 April 2019; online 3 May 2019)

In the molecular structure of the title compound, C₁₀H₁₀N₄O₂·H₂O, the angle between the triazole and arene rings is 87.39 (5)°. The water of crystallization connects the molecules in the crystal packing. The crystal structure exhibits N—H⋯O, O—H⋯O and O—H⋯N interactions, resulting in the formation of a three-dimensional framework. The intermolecular interactions were identified and quantified using Hirshfeld surface analysis.

Keywords: crystal structure; triazole compounds; crystal packing; hydrogen bonding; Hirshfeld surface analysis..

CCDC reference: 1912546

1. Chemical context

Triazoles are a class of compounds that have aroused chemical interest because of their wide range of applications, including their biological relevance and the development of new materials. Triazoles have potent antifungal activity, being an important class of drugs (Peyton et al., 2015 ). Their antitubercular (Zhang et al., 2017 ), anticancer (Teixeira et al., 2019 ), antimicrobial (Yadav et al., 2018 ) and antiviral (Jordão et al., 2009 ) activities have also been evaluated. This class of compounds has also aroused interest in materials chemistry, mainly in the development of systems with uptake capacity for both CO₂ and H₂ (Mukherjee et al., 2019 ).

2. Structural commentary

The title molecule (Fig. 1) is formed by planar aniline and triazolic rings, which subtend a dihedral angle of 87.41 (5)°. Atoms O1 and O2 are located 0.237 (2) and 0.208 (2) Å, respectively, outside the plane of the triazole ring. The methyl group exhibits occupational disorder of the hydrogen atoms.

Figure 1
The molecular structure of the title compound with anisotropic atomic displacement ellipsoids shown at the 50% probability level.

3. Supramolecular features

The crystal packing is stabilized by N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds between the water molecule and the organic molecule. The supramolecular arrangement is formed by four hydrogen bonds (Table 1): (A) N4—H4⋯O1Wⁱⁱ, (B) O1—H1⋯O1Wⁱ, (C) O1W—H1WA⋯O2ⁱⁱⁱ and (D) O1W—H1WB⋯N1. Separately, these hydrogen bonds do not form nets in the structure. However, when combined, they generate interesting supramolecular systems. The combination of the (A:B), (B:C) and (B:D) interactions result in intermolecular rings with R₂⁴(18), R₄⁴(12) and R₄⁴(14) motifs, respectively. Representations of the R₄⁴(12) and R₄⁴(14) motifs are illustrated in Fig. 2). A C₂²(9) motif is observed along [ $[\overline{1}]$ 10] (A:C interactions) (Fig. 3a), a C₂²(7) motif along [010] (A:D interactions) (Fig. 3b) and a C₂²(7) motif along [100] (C:D interactions).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1Wⁱ	0.94 (2)	1.68 (3)	2.6030 (19)	167 (2)
N4—H4⋯O1Wⁱⁱ	0.91 (2)	2.22 (2)	3.111 (2)	169.2 (19)
O1W—H1WA⋯O2ⁱⁱⁱ	0.82 (3)	1.99 (3)	2.773 (2)	159 (2)
O1W—H1WB⋯N1	0.92 (3)	1.88 (3)	2.800 (2)	172 (2)
Symmetry codes: (i) -x, -y+2, -z; (ii) x, y-1, z; (iii) x+1, y, z.

Figure 2
A partial packing diagram showing the hydrogen-bond network along the a axis and the R₄⁴(12) (green) and R₄⁴(14) (yellow) motifs. All hydrogen atoms bonded to carbon are omitted for clarity.

Figure 3
Views along the c axis showing the layers consolidated by the hydrogen-bond network: (a) a C₂²(7) chain along the b-axis direction and (b) a C₂²(9) chain along [ $[\overline{1}]$ 10]. All hydrogen atoms bonded to carbon are omitted for clarity.

4. Hirshfeld surface analysis

For an unequivocal description of the supramolecular system, Hirshfeld Surface (HS) analysis was performed. The isosurface was plotted for the weight function equal to 0.5. The red areas in Fig. 4 correspond to short contacts between atoms inside and outside the surface atom, d_i and d_e. There are three spots on the surface, and in the corresponding fingerprint plot (FPP; Fig. 5), they are represented as sharp spikes. Chemically, they correspond to classical hydrogen bonds. Two of these involve interactions between the carboxyl group and the water molecule while the third is the interaction between N-triazole and the water molecule. These hydrogen bonds are the shortest contacts, assigned in the FPP as O⋯H and N⋯H. The N⋯H interaction contributes 15.8% to the HS, while the O⋯H interaction corresponds to 18.1%. The majority of the interactions are H⋯H, being equal to 36.0%.

Figure 4
Hirshfeld surface mapped with d_norm.

Figure 5
The fingerprint plots for the title compound.

5. Database survey

A research of the Cambridge Structural Database (CSD version 5.40, update of November 2018; Groom et al., 2016 ) for N-phenyl-1H-1,2,3-triazol-1-amine derivatives gave 18 hits for structures that include atomic coordinates. These results include alcohols, esters and a carbohydrazide. The molecular structures of these compounds show dihedral angles between the triazole and aniline rings in the range 76 to 89°. These values are affected by the hydrogen bonds in the crystal packing. In addition, in studies of halogenated phenyl derivatives, differences in C—H⋯π interactions were shown to result in changes in the crystal packing (Jordão et al., 2012 ).

6. Vibrational spectrum

Fig. 6 shows the IR spectrum measured in ATR mode (ν_max, cm⁻¹) which exhibits the following characteristic bands: 3205 (N—H stretching); 2984 (methyl C—H stretching); 1725 (C=O stretching); 1600 (>C=N stretching); 1496 (aromatic C=C stretching); 1348 (C—N stretching of triazole); 1208 (C—O stretching) for the esther and 3431 (OH stretching); 3268 (N—H stretching); 1695 (C=O stretching); 1589 (>C=N stretching); 1496 (aromatic C=C stretching); 1381 (C—N stretching of triazole); 1259 (C—O stretching) for the acid.

Figure 6
IR spectrum of the title compound.

7. Synthesis and crystallization

The title compound was synthesized by the alkaline hydrolysis of 5-methyl-1-(phenylamino)-1H-[1,2,3]-triazole-4-carboxylic acid ethyl ester (Jordão et al., 2009), 1. 3.6 mmol of 1 were dissolved in 30.0 ml of a sodium hydroxide solution (0.1 mol L⁻¹) (NaOH, VETEC). This mixture was refluxed at 373 K for about 48 h. The product was neutralized using dilute hydrochloric acid (HCl, VETEC), filtered and dried in vacuo. The title compound was dissolved in methanol and kept at room temperature. After a few days, colourless block-shaped crystals, suitable for X-ray analysis, were obtained by slow evaporation (yield 83%).

¹H NMR (500 MHz, C₂D₆OS): 10.218 (1H, s), 9.887 (1H, s), 7.215 (2H, m), 6.872 (1H, m), 6.390(2H, d, J = 3Hz), 3.295 (1H, s).

8. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were located in a difference-Fourier map and freely refined except for hydrogen atoms bound to C10 which are disordered (occupancy 0.5) and were refined using a riding model with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₁₀N₄O₂·H₂O
M_r	236.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.2288 (14), 6.8265 (14), 23.922 (5)
β (°)	98.69 (3)
V (Å³)	1167.0 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.24 × 0.20 × 0.06

Data collection
Diffractometer	Bruker KappaCCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.701, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	11378, 2207, 1559
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.100, 1.04
No. of reflections	2207
No. of parameters	191
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15
Computer programs: COLLECT (Bruker, 2004 ), DIRAX/LSQ (Duisenberg, 1992 ), EVALCCD (Duisenberg et al., 2003 ), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2008 ).

Supporting information

CCDC reference: 1912546

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005711/ex2020sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005711/ex2020Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989019005711/ex2020Isup3.cml

checkCIF report

Computing details top

Data collection: COLLECT (Bruker, 2004); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Anilino-5-methyl-1H-1,2,3-triazole-4-carboxylic acid monohydrate top

Crystal data top

C₁₀H₁₀N₄O₂·H₂O	F(000) = 496
M_r = 236.24	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.2288 (14) Å	Cell parameters from 11378 reflections
b = 6.8265 (14) Å	θ = 3.1–25.2°
c = 23.922 (5) Å	µ = 0.10 mm⁻¹
β = 98.69 (3)°	T = 298 K
V = 1167.0 (4) Å³	Block, colourless
Z = 4	0.24 × 0.20 × 0.06 mm

Data collection top

Bruker KappaCCD diffractometer	2207 independent reflections
Horizonally mounted graphite crystal monochromator	1559 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm^-1	R_int = 0.042
CCD scans	θ_max = 25.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −8→8
T_min = 0.701, T_max = 0.745	k = −8→7
11378 measured reflections	l = −28→29

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)] = 0.041	w = 1/[σ²(F_o²) + (0.0451P)² + 0.2317P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.100	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.18 e Å⁻³
2207 reflections	Δρ_min = −0.15 e Å⁻³
191 parameters	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.016 (3)

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	Occ. (<1)
N1	0.1134 (2)	0.5773 (2)	0.07579 (6)	0.0470 (4)
N2	0.1952 (2)	0.4253 (2)	0.10201 (7)	0.0490 (4)
N3	0.0553 (2)	0.3016 (2)	0.11042 (6)	0.0408 (4)
N4	0.0956 (2)	0.1211 (2)	0.13675 (6)	0.0456 (4)
O1	−0.11452 (18)	0.8386 (2)	0.01606 (6)	0.0548 (4)
O2	−0.37050 (18)	0.6983 (2)	0.03987 (6)	0.0626 (4)
C1	−0.2030 (3)	0.7017 (3)	0.04017 (7)	0.0416 (4)
C2	−0.0763 (2)	0.5512 (3)	0.06831 (7)	0.0379 (4)
C3	−0.1165 (2)	0.3727 (2)	0.09034 (7)	0.0375 (4)
C4	0.1777 (2)	0.1351 (2)	0.19481 (7)	0.0387 (4)
C5	0.3163 (3)	0.0044 (3)	0.21538 (9)	0.0536 (5)
C6	0.3937 (3)	0.0088 (3)	0.27196 (9)	0.0608 (6)
C7	0.3320 (3)	0.1427 (3)	0.30781 (9)	0.0552 (6)
C8	0.1928 (3)	0.2721 (3)	0.28731 (9)	0.0575 (5)
C9	0.1139 (3)	0.2681 (3)	0.23076 (8)	0.0502 (5)
C10	−0.2922 (3)	0.2638 (3)	0.09330 (8)	0.0507 (5)
H10A	−0.397146	0.341238	0.076648	0.076*	0.5
H10B	−0.290788	0.142584	0.073046	0.076*	0.5
H10C	−0.302575	0.237247	0.132110	0.076*	0.5
H10D	−0.263193	0.139474	0.111221	0.076*	0.5
H10E	−0.369552	0.338129	0.114823	0.076*	0.5
H10F	−0.357764	0.243466	0.055760	0.076*	0.5
O1W	0.3100 (2)	0.9111 (2)	0.05054 (6)	0.0509 (4)
H1	−0.199 (3)	0.926 (4)	−0.0049 (10)	0.081 (7)*
H9	0.022 (3)	0.353 (3)	0.2172 (8)	0.058 (6)*
H5	0.359 (3)	−0.091 (3)	0.1907 (9)	0.067 (6)*
H6	0.495 (3)	−0.078 (3)	0.2851 (9)	0.076 (7)*
H7	0.388 (3)	0.149 (3)	0.3456 (10)	0.067 (6)*
H8	0.139 (3)	0.367 (4)	0.3125 (10)	0.083 (7)*
H4	0.170 (3)	0.056 (3)	0.1157 (9)	0.063 (6)*
H1WA	0.415 (4)	0.876 (4)	0.0455 (10)	0.074 (8)*
H1WB	0.241 (4)	0.800 (4)	0.0552 (10)	0.089 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0395 (9)	0.0483 (9)	0.0530 (9)	0.0066 (7)	0.0060 (7)	0.0148 (8)
N2	0.0410 (9)	0.0486 (9)	0.0570 (10)	0.0059 (8)	0.0067 (7)	0.0150 (8)
N3	0.0423 (9)	0.0390 (8)	0.0404 (8)	0.0054 (7)	0.0043 (6)	0.0064 (7)
N4	0.0573 (10)	0.0355 (9)	0.0431 (9)	0.0114 (7)	0.0046 (7)	0.0046 (7)
O1	0.0467 (8)	0.0527 (8)	0.0641 (9)	0.0101 (7)	0.0057 (7)	0.0233 (7)
O2	0.0394 (8)	0.0704 (10)	0.0785 (10)	0.0141 (7)	0.0102 (7)	0.0187 (8)
C1	0.0426 (11)	0.0450 (11)	0.0374 (9)	0.0082 (9)	0.0068 (8)	0.0011 (8)
C2	0.0361 (10)	0.0419 (10)	0.0355 (9)	0.0054 (8)	0.0051 (7)	0.0020 (8)
C3	0.0407 (10)	0.0403 (10)	0.0313 (9)	0.0053 (8)	0.0053 (7)	−0.0019 (8)
C4	0.0390 (10)	0.0348 (9)	0.0428 (10)	0.0029 (8)	0.0080 (8)	0.0070 (8)
C5	0.0580 (13)	0.0519 (12)	0.0522 (12)	0.0201 (10)	0.0129 (10)	0.0078 (10)
C6	0.0533 (13)	0.0678 (15)	0.0594 (14)	0.0172 (11)	0.0027 (10)	0.0192 (12)
C7	0.0569 (13)	0.0638 (14)	0.0433 (11)	−0.0076 (11)	0.0022 (10)	0.0109 (11)
C8	0.0658 (14)	0.0566 (13)	0.0506 (12)	0.0041 (11)	0.0107 (10)	−0.0039 (11)
C9	0.0498 (12)	0.0487 (12)	0.0512 (12)	0.0146 (10)	0.0045 (9)	0.0020 (10)
C10	0.0478 (11)	0.0478 (11)	0.0557 (12)	−0.0048 (9)	0.0053 (9)	−0.0045 (9)
O1W	0.0430 (9)	0.0445 (8)	0.0649 (9)	0.0073 (7)	0.0074 (7)	0.0108 (7)

Geometric parameters (Å, º) top

N1—N2	1.307 (2)	C5—H5	0.96 (2)
N1—C2	1.367 (2)	C6—C7	1.373 (3)
N2—N3	1.356 (2)	C6—H6	0.96 (2)
N3—C3	1.352 (2)	C7—C8	1.372 (3)
N3—N4	1.394 (2)	C7—H7	0.93 (2)
N4—C4	1.429 (2)	C8—C9	1.387 (3)
N4—H4	0.91 (2)	C8—H8	1.00 (2)
O1—C1	1.314 (2)	C9—H9	0.90 (2)
O1—H1	0.94 (2)	C10—H10A	0.9600
O2—C1	1.210 (2)	C10—H10B	0.9600
C1—C2	1.470 (2)	C10—H10C	0.9600
C2—C3	1.376 (2)	C10—H10D	0.9600
C3—C10	1.482 (2)	C10—H10E	0.9600
C4—C5	1.376 (3)	C10—H10F	0.9600
C4—C9	1.377 (3)	O1W—H1WA	0.82 (3)
C5—C6	1.385 (3)	O1W—H1WB	0.92 (3)

N2—N1—C2	109.36 (14)	C6—C7—H7	120.2 (13)
N1—N2—N3	105.80 (14)	C7—C8—C9	120.5 (2)
C3—N3—N2	112.91 (14)	C7—C8—H8	122.1 (13)
C3—N3—N4	126.55 (15)	C9—C8—H8	117.3 (14)
N2—N3—N4	120.53 (14)	C4—C9—C8	119.66 (19)
N3—N4—C4	114.07 (14)	C4—C9—H9	119.7 (13)
N3—N4—H4	106.5 (13)	C8—C9—H9	120.6 (13)
C4—N4—H4	112.3 (14)	C3—C10—H10A	109.5
C1—O1—H1	111.4 (14)	C3—C10—H10B	109.5
O2—C1—O1	124.32 (17)	H10A—C10—H10B	109.5
O2—C1—C2	122.91 (17)	C3—C10—H10C	109.5
O1—C1—C2	112.77 (15)	H10A—C10—H10C	109.5
N1—C2—C3	109.33 (15)	H10B—C10—H10C	109.5
N1—C2—C1	120.80 (15)	C3—C10—H10D	109.5
C3—C2—C1	129.87 (16)	H10A—C10—H10D	141.1
N3—C3—C2	102.58 (14)	H10B—C10—H10D	56.3
N3—C3—C10	123.43 (16)	H10C—C10—H10D	56.3
C2—C3—C10	133.97 (16)	C3—C10—H10E	109.5
C5—C4—C9	119.92 (18)	H10A—C10—H10E	56.3
C5—C4—N4	118.51 (16)	H10B—C10—H10E	141.1
C9—C4—N4	121.46 (16)	H10C—C10—H10E	56.3
C4—C5—C6	120.0 (2)	H10D—C10—H10E	109.5
C4—C5—H5	120.3 (13)	C3—C10—H10F	109.5
C6—C5—H5	119.7 (13)	H10A—C10—H10F	56.3
C7—C6—C5	120.3 (2)	H10B—C10—H10F	56.3
C7—C6—H6	120.8 (13)	H10C—C10—H10F	141.1
C5—C6—H6	118.8 (13)	H10D—C10—H10F	109.5
C8—C7—C6	119.7 (2)	H10E—C10—H10F	109.5
C8—C7—H7	120.1 (13)	H1WA—O1W—H1WB	108 (2)

C2—N1—N2—N3	0.73 (19)	N1—C2—C3—N3	0.32 (18)
N1—N2—N3—C3	−0.55 (19)	C1—C2—C3—N3	−179.89 (16)
N1—N2—N3—N4	178.75 (14)	N1—C2—C3—C10	−178.06 (18)
C3—N3—N4—C4	−114.38 (18)	C1—C2—C3—C10	1.7 (3)
N2—N3—N4—C4	66.4 (2)	N3—N4—C4—C5	−141.88 (17)
N2—N1—C2—C3	−0.69 (19)	N3—N4—C4—C9	41.9 (2)
N2—N1—C2—C1	179.51 (15)	C9—C4—C5—C6	−1.1 (3)
O2—C1—C2—N1	−168.96 (17)	N4—C4—C5—C6	−177.43 (18)
O1—C1—C2—N1	10.7 (2)	C4—C5—C6—C7	0.3 (3)
O2—C1—C2—C3	11.3 (3)	C5—C6—C7—C8	0.1 (3)
O1—C1—C2—C3	−169.10 (17)	C6—C7—C8—C9	0.2 (3)
N2—N3—C3—C2	0.13 (18)	C5—C4—C9—C8	1.4 (3)
N4—N3—C3—C2	−179.11 (15)	N4—C4—C9—C8	177.62 (18)
N2—N3—C3—C10	178.74 (15)	C7—C8—C9—C4	−1.0 (3)
N4—N3—C3—C10	−0.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1Wⁱ	0.94 (2)	1.68 (3)	2.6030 (19)	167 (2)
N4—H4···O1Wⁱⁱ	0.91 (2)	2.22 (2)	3.111 (2)	169.2 (19)
O1W—H1WA···O2ⁱⁱⁱ	0.82 (3)	1.99 (3)	2.773 (2)	159 (2)
O1W—H1WB···N1	0.92 (3)	1.88 (3)	2.800 (2)	172 (2)

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

Acknowledgements

The authors would like to thank LAME–UFF and LDRX–UFF for analyses.

Funding information

Funding for this research was provided by: Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro; Conselho Nacional de Desenvolvimento Científico e Tecnológico (grant No. 311142/2017-6).

References

Bruker (2004). COLLECT. Bruker AXS BV, Delft, The Netherlands. Google Scholar
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Duisenberg, A. J. M. (1992). J. Appl. Cryst. 25, 92–96. CrossRef CAS Web of Science IUCr Journals Google Scholar
Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003). J. Appl. Cryst. 36, 220–229. Web of Science 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
Jordão, A. K., Afonso, P. P., Ferreira, V. F., de Souza, M. C. B. V., Almeida, M. C. B., Beltrame, C. O., Paiva, D. P., Wardell, S. M. S. V., Wardell, J. L., Tiekink, E. R. T., Damaso, C. R. & Cunha, A. C. (2009). Eur. J. Med. Chem. 44, 3777–3783. Web of Science PubMed Google Scholar
Jordão, A. K., Ferreira, V. F., Cunha, A. C., Wardell, J. L., Wardell, S. M. S. V. & Tiekink, E. R. T. (2012). CrystEngComm, 14, 6534–6539. Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mukherjee, S., Das, M., Manna, A., Krishna, R. & Das, S. (2019). J. Mater. Chem. A, 7, 1055–1068. Web of Science CrossRef CAS Google Scholar
Peyton, L. R., Gallagher, S. & Hashemzadeh, M. (2015). Drugs Today, 51, 705–718. Web of Science CAS PubMed 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
Teixeira, R. R., Silva, A. M., Siqueira, R. P., Gonçalves, V. H. S., Pereira, H. S., Ferreira, R. S., Costa, A. V., Melo, E. B., Paula, F. R., Ferreira, M. M. C. & Bressan, G. C. (2019). J. Braz. Chem. Soc. 30, 541–561. CAS Google Scholar
Yadav, P., Lal, K., Kumar, L., Kumar, A., Kumar, A., Paul, A. K. & Kumar, R. (2018). Eur. J. Med. Chem. 155, 263–274. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhang, A., Xu, Z., Gao, G., Ren, Q. C., Chang, L., Lv, Z. S. & Feng, L. S. (2017). Eur. J. Med. Chem. 138, 501–513. Web of Science CrossRef CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.