2-[(5-Methyl-1,3,4-thia­diazol-2-yl)sulfan­yl]-N′-(4-nitro­benzyl­idene)acetohydrazide monohydrate

Nidhishree, M.; Gomathi, S.; Nirmalram, J.S.; Mathivathanan, L.

doi:10.1107/S2414314625003645

organic compounds

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ISSN: 2414-3146

Volume 10| Part 4| April 2025| x250364

https://doi.org/10.1107/S2414314625003645

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2-[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-N′-(4-nitrobenzylidene)acetohydrazide monohydrate

Murugan Nidhishree,^a Sundaramoorthy Gomathi,^a ^* Jeyaraman Selvaraj Nirmalram ^b and Logesh Mathivathanan ^c

^aDepartment of Chemistry, Periyar Maniammai Institute of Science & Technology, Thanjavur-613403, Tamilnadu, India, ^bDepartment of Chemistry, Research and Development Cell, PRIST Deemed to be University, Thanjavur-613403, Tamilnadu, India, and ^cDepartment of Chemistry, School of Advanced Sciences, Vellore Institute of Technology, Vellore-632014, Tamil Nadu, India
^*Correspondence e-mail: gomathichemist@pmu.edu

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 March 2025; accepted 22 April 2025; online 24 April 2025)

In the title hydrate, C₁₂H₁₁N₅O₃S₂·H₂O, the dihedral angle between the aromatic rings is 9.6 (3)°. In the crystal, N—H⋯O and O—H⋯N hydrogen bonds link the components into (101) sheets.

Keywords: crystal structure; 1,3,4-thiadiazole; hydrogen bonds.

CCDC reference: 2445786

Structure description

1,3,4-Thiadiazole derivatives exhibit various biological activities such as cytotoxic (Janowska et al., 2020 ), anticancer (Hekal et al., 2023 ), anticonvulsant (Luszczki et al., 2015 ), anti-epileptic (Anthwal & Nain, 2022 ), antinociceptive (Altıntop et al., 2016 ), antitubercular (Jain et al., 2013 ), antimicrobial, antifungal and anthelmintic activities (Bhinge et al., 2015 ). As part of the ongoing studies in this area, the present work describes the synthesis and structure of the title hydrate, C₁₂H₁₁N₅O₃S₂·H₂O (I) (Fig. 1 and scheme).

Figure 1
The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level.

The dihedral angle between the C2/C5/N3/N4/S1 1,3,4-thiadiazole ring and the C10–C15 benzylidene ring is 9.6 (3)°. The torsion angles O1—C8—N1—N2, C7—C8—N1—N2 and C8—N1—N2—C9 are 177.1 (5), −2.5 (8) and 174.6 (5)°, respectively. The first and third of these indicate that the molecule adopts a near-planar trans conformation. The small value for the second appears to minimize steric hindrance and maintains overall near-planarity. The bond angles for the hydrazide nitrogen atoms (N1 and N2) are close to 120°, indicative of the expected sp² hybridization (Mohan et al., 2011 ). Overall, the organic molecule is close to planar (r.m.s. deviation for the non-hydrogen atoms = 0.139 Å).

In the crystal, the components are linked by N—H⋯O_w and O_w—H⋯N (w = water) hydrogen bonds (Table 1), generating infinite (10 $[\overline{1}]$ ) sheets. Various supramolecular assemblies arise from this connectivity including R₄⁴(10) R₂²(24), R₃³(17), R₄⁴(10), R₃³(17) and R₂²(24) loops (Fig. 2). Two weak C—H⋯O interactions also occur.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.82 (4)	2.08 (4)	2.900 (8)	176 (5)
O4—H4A⋯N4ⁱⁱ	0.72 (9)	2.32 (9)	3.037 (8)	175 (10)
O4—H4B⋯N3	0.75 (8)	2.15 (9)	2.898 (8)	176 (13)
C7—H7B⋯O3ⁱⁱⁱ	0.97	2.51	3.400 (7)	153
C12—H12⋯O1^iv	0.93	2.46	3.349 (6)	159
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) ; (iii) ; (iv) $[x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Part of a supramolecular layer in the crystal of (I) showing various supramolecular motifs. Symmetry codes (i) −1 + x, y, z; (ii) −x, −y, −z; (iii) $[{1\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z; (iv) − $[{3\over 2}]$ + x, $[{1\over 2}]$ − y, − $[{1\over 2}]$ + z; (v) 1 − x, −y, 1 − z].

The quantitative contribution of each type interaction to the Hirshfeld surface is provided in the two-dimensional finger print plots and it is supported by the HS mapped with d_norm. The O⋯H/H⋯O contacts provide a maximum contribution (28.4%) through strong hydrogen bonding, followed by H⋯H (25.2%), and a significant role is played by N⋯H/H⋯N (9.2%) contacts. The other contact types S⋯H/H⋯S (7.7%), C⋯H/H⋯C (8.6%) O⋯C/C⋯O (5.4%) N⋯C/C⋯N (3.9%) and S⋯O/O⋯S (3.4%) presumably play a minor role on the crystal packing of (I) (see Figs. S1 and S2 in the supporting information).

Synthesis and crystallization

The title compound was synthesized by mixing 20 mL of an ethanolic solution of (5-methyl-[1,3,4]lthiadiazol-2-ylsulfanyl) acetic acid hydrazide (0.25 mmol) and ethanol:water mixture (3:1 v/v) 4-nitrobenzaldehyde (0.25 mmol). The resulting mixture was refluxed under basic conditions for approximately 2 h. The resultant product was dissolved in 20 mL of ethanol, and the solution was allowed to crystallize via slow evaporation at room temperature, from which golden crystals of the title compound were harvested.

Refinement

The crystal data, data collection and structure refinement details for the compound are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₂H₁₁N₅O₃S₂·H₂O
M_r	355.39
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	4.9431 (3), 18.3181 (11), 17.2223 (9)
β (°)	95.557 (2)
V (Å³)	1552.12 (16)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.37
Crystal size (mm)	0.14 × 0.10 × 0.04

Data collection
Diffractometer	Bruker D8 Quest
No. of measured, independent and observed [I > 2σ(I)] reflections	7776, 2857, 1703
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.090, 0.155, 1.22
No. of reflections	2857
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.35
Computer programs: APEX2 and SAINT (Bruker, 2016 ), SHELXT2018 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), PLATON (Spek, 2020 ), Mercury (Macrae et al., 2020 ), POVRay (Cason, 2004 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2445786

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314625003645/hb4512sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625003645/hb4512Isup2.hkl

The supporting information contains Two dimensional fingerprint plot showing the total contribution of individual types of interactions and HS mapped with dnorm. DOI: https://doi.org/10.1107/S2414314625003645/hb4512sup3.pdf

Supporting information file. DOI: https://doi.org/10.1107/S2414314625003645/hb4512Isup4.cml

checkCIF report

Computing details top

2-[(5-Methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-N'-(4-nitrobenzylidene)acetohydrazide monohydrate top

Crystal data top

C₁₂H₁₁N₅O₃S₂·H₂O	F(000) = 736
M_r = 355.39	D_x = 1.521 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2857 reflections
a = 4.9431 (3) Å	θ = 2.5–26.3°
b = 18.3181 (11) Å	µ = 0.37 mm⁻¹
c = 17.2223 (9) Å	T = 273 K
β = 95.557 (2)°	Trapezoid, gold
V = 1552.12 (16) Å³	0.14 × 0.10 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.098
φ and ω scans	θ_max = 26.3°, θ_min = 2.5°
7776 measured reflections	h = −5→5
2857 independent reflections	k = −22→19
1703 reflections with I > 2σ(I)	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.090	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.155	W = 1/[Σ²(FO²) + 5.0708P] WHERE P = (FO² + 2FC²)/3
S = 1.22	(Δ/σ)_max < 0.001
2857 reflections	Δρ_max = 0.35 e Å⁻³
221 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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.

The nitrogen- and oxygen-bound hydrogen atoms (H1, H14A & H14B) were located from the difference-Fourier map and refined freely. All other H atoms were positioned geometrically and refined via a riding model.

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

	x	y	z	U_iso*/U_eq
S1	0.3438 (3)	0.03917 (9)	0.27832 (9)	0.0388 (5)
S2	0.7558 (3)	0.16604 (9)	0.27385 (9)	0.0406 (6)
O1	0.8363 (9)	0.2756 (2)	0.1699 (2)	0.0502 (17)
O2	−0.8321 (10)	0.0733 (3)	−0.2101 (3)	0.0619 (17)
O3	−0.7278 (10)	−0.0085 (2)	−0.1227 (3)	0.0576 (17)
N1	0.5049 (11)	0.2563 (3)	0.0730 (3)	0.0344 (17)
N2	0.2957 (10)	0.2128 (3)	0.0442 (3)	0.0329 (17)
N3	0.7537 (10)	0.0603 (3)	0.3767 (3)	0.0419 (17)
N4	0.6281 (11)	−0.0020 (3)	0.4009 (3)	0.0423 (17)
N5	−0.6936 (11)	0.0505 (3)	−0.1527 (3)	0.0421 (19)
C2	0.6256 (12)	0.0873 (3)	0.3140 (3)	0.033 (2)
O4	1.1824 (13)	0.1213 (3)	0.4840 (4)	0.0509 (19)
C5	0.4153 (12)	−0.0206 (3)	0.3560 (4)	0.038 (2)
C6	0.2509 (12)	−0.0867 (3)	0.3681 (4)	0.049 (3)
C7	0.5363 (12)	0.1752 (3)	0.1848 (3)	0.039 (2)
C8	0.6405 (13)	0.2400 (3)	0.1429 (3)	0.034 (2)
C9	0.1601 (12)	0.2331 (3)	−0.0185 (3)	0.035 (2)
C10	−0.0591 (11)	0.1862 (3)	−0.0527 (3)	0.0319 (19)
C11	−0.2248 (12)	0.2078 (3)	−0.1184 (3)	0.038 (2)
C12	−0.4307 (12)	0.1647 (3)	−0.1523 (3)	0.039 (2)
C13	−0.4703 (11)	0.0975 (3)	−0.1198 (3)	0.032 (2)
C14	−0.3105 (13)	0.0738 (3)	−0.0551 (4)	0.044 (2)
C15	−0.1059 (13)	0.1177 (3)	−0.0217 (4)	0.042 (2)
H1	0.557 (9)	0.292 (2)	0.050 (3)	0.006 (13)*
H6A	0.29906	−0.10554	0.41958	0.0740*
H6B	0.28606	−0.12305	0.33019	0.0740*
H6C	0.06142	−0.07423	0.36230	0.0740*
H7A	0.35003	0.18331	0.19596	0.0460*
H7B	0.54276	0.13154	0.15321	0.0460*
H9	0.19963	0.27696	−0.04217	0.0420*
H11	−0.19521	0.25314	−0.14028	0.0460*
H12	−0.54010	0.18052	−0.19606	0.0460*
H14	−0.34078	0.02823	−0.03384	0.0530*
H15	0.00261	0.10145	0.02197	0.0500*
H4A	1.231 (18)	0.092 (5)	0.509 (5)	0.10 (4)*
H4B	1.070 (16)	0.104 (5)	0.458 (5)	0.09 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0353 (9)	0.0392 (9)	0.0406 (10)	−0.0011 (8)	−0.0025 (7)	0.0083 (8)
S2	0.0422 (10)	0.0379 (9)	0.0388 (10)	−0.0074 (8)	−0.0111 (8)	0.0063 (8)
O1	0.056 (3)	0.048 (3)	0.044 (3)	−0.026 (2)	−0.009 (2)	0.004 (2)
O2	0.060 (3)	0.064 (3)	0.056 (3)	−0.010 (3)	−0.023 (3)	0.000 (3)
O3	0.067 (3)	0.041 (3)	0.064 (3)	−0.018 (3)	0.002 (3)	0.007 (3)
N1	0.043 (3)	0.028 (3)	0.032 (3)	−0.010 (3)	0.002 (3)	0.007 (2)
N2	0.033 (3)	0.035 (3)	0.030 (3)	−0.003 (2)	0.000 (2)	−0.003 (2)
N3	0.045 (3)	0.043 (3)	0.035 (3)	−0.003 (3)	−0.010 (3)	0.010 (3)
N4	0.046 (3)	0.045 (3)	0.036 (3)	0.006 (3)	0.005 (3)	0.017 (3)
N5	0.045 (3)	0.044 (4)	0.037 (3)	−0.001 (3)	0.003 (3)	−0.010 (3)
C2	0.035 (4)	0.033 (3)	0.030 (4)	0.003 (3)	0.002 (3)	0.003 (3)
O4	0.061 (4)	0.043 (3)	0.046 (3)	0.006 (3)	−0.009 (3)	−0.004 (3)
C5	0.033 (4)	0.039 (4)	0.041 (4)	0.009 (3)	0.005 (3)	0.005 (3)
C6	0.040 (4)	0.044 (4)	0.065 (5)	−0.005 (3)	0.010 (4)	0.020 (4)
C7	0.043 (4)	0.035 (4)	0.036 (4)	−0.010 (3)	−0.006 (3)	0.007 (3)
C8	0.042 (4)	0.027 (3)	0.031 (4)	0.000 (3)	−0.001 (3)	−0.004 (3)
C9	0.037 (4)	0.037 (4)	0.031 (4)	0.002 (3)	0.002 (3)	0.001 (3)
C10	0.029 (3)	0.037 (4)	0.030 (3)	0.003 (3)	0.004 (3)	−0.002 (3)
C11	0.041 (4)	0.034 (3)	0.038 (4)	0.003 (3)	−0.004 (3)	0.014 (3)
C12	0.039 (4)	0.045 (4)	0.030 (4)	0.000 (3)	−0.006 (3)	0.002 (3)
C13	0.028 (4)	0.034 (4)	0.032 (4)	−0.002 (3)	0.001 (3)	−0.003 (3)
C14	0.048 (4)	0.038 (4)	0.046 (4)	0.000 (3)	0.003 (3)	0.011 (3)
C15	0.041 (4)	0.042 (4)	0.040 (4)	0.001 (3)	−0.010 (3)	0.014 (3)

Geometric parameters (Å, º) top

S1—C2	1.712 (6)	C10—C15	1.392 (8)
S1—C5	1.738 (7)	C10—C11	1.389 (8)
S2—C2	1.749 (6)	C11—C12	1.373 (8)
S2—C7	1.799 (6)	C12—C13	1.374 (8)
O1—C8	1.221 (7)	C13—C14	1.372 (8)
O2—N5	1.220 (7)	C14—C15	1.374 (9)
O3—N5	1.217 (7)	O4—H4A	0.72 (9)
N1—N2	1.361 (8)	O4—H4B	0.75 (8)
N1—C8	1.353 (8)	C6—H6C	0.9600
N2—C9	1.270 (7)	C6—H6A	0.9600
N3—N4	1.383 (8)	C6—H6B	0.9600
N3—C2	1.296 (7)	C7—H7B	0.9700
N4—C5	1.290 (8)	C7—H7A	0.9700
N5—C13	1.470 (8)	C9—H9	0.9300
N1—H1	0.82 (4)	C11—H11	0.9300
C5—C6	1.484 (8)	C12—H12	0.9300
C7—C8	1.506 (8)	C14—H14	0.9300
C9—C10	1.461 (8)	C15—H15	0.9300

C2—S1—C5	87.2 (3)	N5—C13—C14	118.7 (5)
C2—S2—C7	101.5 (3)	N5—C13—C12	119.9 (5)
N2—N1—C8	119.3 (5)	C12—C13—C14	121.4 (5)
N1—N2—C9	117.3 (5)	C13—C14—C15	119.8 (5)
N4—N3—C2	111.6 (5)	C10—C15—C14	120.7 (6)
N3—N4—C5	113.7 (5)	H4A—O4—H4B	103 (10)
O2—N5—O3	123.9 (6)	C5—C6—H6B	109.00
O2—N5—C13	117.0 (5)	C5—C6—H6C	109.00
O3—N5—C13	119.1 (5)	C5—C6—H6A	109.00
C8—N1—H1	117 (3)	H6A—C6—H6C	110.00
N2—N1—H1	124 (3)	H6B—C6—H6C	109.00
S1—C2—N3	114.7 (4)	H6A—C6—H6B	109.00
S2—C2—N3	118.4 (4)	S2—C7—H7B	111.00
S1—C2—S2	126.9 (3)	C8—C7—H7A	110.00
N4—C5—C6	123.9 (6)	C8—C7—H7B	110.00
S1—C5—N4	112.9 (4)	H7A—C7—H7B	109.00
S1—C5—C6	123.3 (5)	S2—C7—H7A	111.00
S2—C7—C8	106.0 (4)	C10—C9—H9	121.00
N1—C8—C7	115.9 (5)	N2—C9—H9	121.00
O1—C8—C7	122.3 (5)	C10—C11—H11	119.00
O1—C8—N1	121.8 (5)	C12—C11—H11	119.00
N2—C9—C10	118.7 (5)	C13—C12—H12	121.00
C11—C10—C15	117.6 (5)	C11—C12—H12	121.00
C9—C10—C11	121.1 (5)	C13—C14—H14	120.00
C9—C10—C15	121.3 (5)	C15—C14—H14	120.00
C10—C11—C12	122.5 (5)	C10—C15—H15	120.00
C11—C12—C13	118.1 (5)	C14—C15—H15	120.00

C5—S1—C2—S2	178.8 (4)	O2—N5—C13—C14	179.8 (6)
C5—S1—C2—N3	0.1 (5)	O3—N5—C13—C12	−179.2 (5)
C2—S1—C5—N4	0.5 (5)	O3—N5—C13—C14	−1.3 (8)
C2—S1—C5—C6	−178.4 (5)	S2—C7—C8—O1	−0.4 (7)
C7—S2—C2—S1	−4.9 (5)	S2—C7—C8—N1	179.2 (4)
C7—S2—C2—N3	173.8 (5)	N2—C9—C10—C11	175.9 (5)
C2—S2—C7—C8	−177.1 (4)	N2—C9—C10—C15	−5.5 (8)
C8—N1—N2—C9	174.6 (5)	C9—C10—C11—C12	179.4 (5)
N2—N1—C8—O1	177.1 (5)	C15—C10—C11—C12	0.7 (8)
N2—N1—C8—C7	−2.5 (8)	C9—C10—C15—C14	−179.1 (6)
N1—N2—C9—C10	177.6 (5)	C11—C10—C15—C14	−0.5 (9)
C2—N3—N4—C5	1.0 (7)	C10—C11—C12—C13	−0.6 (9)
N4—N3—C2—S1	−0.6 (6)	C11—C12—C13—N5	178.1 (5)
N4—N3—C2—S2	−179.5 (4)	C11—C12—C13—C14	0.3 (8)
N3—N4—C5—S1	−1.0 (7)	N5—C13—C14—C15	−177.9 (6)
N3—N4—C5—C6	177.9 (5)	C12—C13—C14—C15	−0.1 (9)
O2—N5—C13—C12	1.9 (8)	C13—C14—C15—C10	0.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.82 (4)	2.08 (4)	2.900 (8)	176 (5)
O4—H4A···N4ⁱⁱ	0.72 (9)	2.32 (9)	3.037 (8)	175 (10)
O4—H4B···N3	0.75 (8)	2.15 (9)	2.898 (8)	176 (13)
C7—H7B···O3ⁱⁱⁱ	0.97	2.51	3.400 (7)	153
C12—H12···O1^iv	0.93	2.46	3.349 (6)	159

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

Acknowledgements

LM thanks Professor Raphael G. Raptis at Florida International University, Miami, for access to the single-crystal X-ray diffraction facility. MN and SG thank R. Shayamaladevi for the support provided during the experimental phase.

References

Altıntop, M. D., Can, Ö. D., Demir Özkay, Ü. & Kaplancıklı, Z. A. (2016). Molecules, 21, 1004. Google Scholar
Anthwal, T. & Nain, S. (2022). Front. Chem. 9, 671212–671212. CrossRef PubMed Google Scholar
Bhinge, S. D., Chature, V. & Sonawane, L. V. (2015). Pharm. Chem. J. 49, 367–372. Web of Science CrossRef CAS Google Scholar
Bruker (2016). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cason, C. J. (2004). POV-RAY. Persistence of Vision Raytracer Pty. Ltd, Victoria, Australia. Google Scholar
Hekal, M. H., Farag, P. S., Hemdan, M. M., El-Sayed, A. A., Hassaballah, A. I. & El-Sayed, W. M. (2023). RSC Adv. 13, 15810–15825. CrossRef CAS PubMed Google Scholar
Jain, A. K., Sharma, S., Vaidya, A., Ravichandran, V. & Agrawal, R. K. (2013). Chem. Biol. Drug Des. 81, 557–576. Web of Science CrossRef CAS PubMed Google Scholar
Janowska, S., Paneth, A. & Wujec, M. (2020). Molecules 25, 4309–4309. CrossRef PubMed Google Scholar
Luszczki, J. J., Karpińska, M., Matysiak, J. & Niewiadomy, A. (2015). Pharmacol. Rep. 67, 588–592. CrossRef CAS PubMed 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
Mohan, S., Ananthan, S., Ramesh, P., Saravanan, D. & Ponnuswamy, M. N. (2011). Acta Cryst. E67, o2612. CSD CrossRef IUCr Journals 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
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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