organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2414-3146

3-[(3,5-Di­methyl-1H-pyrazol-1-yl)meth­yl]-4-(4-methyl­phen­yl)-4,5-di­hydro-1H-1,2,4-triazole-5-thione

aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, 71515 Assiut, Egypt, fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, and gFaculty of Pharmacy, Medicinal Chemistry Department, Assiut University, Assiut 71526, Egypt
*Correspondence e-mail: shaabankamel@yahoo.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 26 January 2017; accepted 30 January 2017; online 3 February 2017)

With the pyrazolyl and p-tolyl groups lying to one side of the plane through the linking 1,2,4-triazole-5-thione residue [forming dihedral angles of 87.05 (8) and 81.41 (7)°, respectively], the title mol­ecule, C15H17N5S, adopts a `pincer' conformation stabilized in part by two intra­molecular C—H⋯π(ring) inter­actions. A three-dimensional network structure is generated by a combination of inter­molecular N—H⋯N and C—H⋯S hydrogen bonds, as well as C—H⋯π(ring) inter­actions.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Pyrazoles and their derivatives are an important class of heterocyclic compounds due to their broad spectrum of biological properties. They exhibit anti-bacterial, anti-depressant (Liu et al., 2008[Liu, X. H., Cui, P., Song, B. A., Bhadury, P. S., Zhu, H. L. & Wang, S. F. (2008). Bioorg. Med. Chem. 16, 4075-4082.]; Yhya et al., 2012[Yhya, R. K., Rai, K. M. L. & Musada, E. A. (2012). Rasayan J. Chem. 5, 376-390.]), anti-oxidant (Abdel-Aziz et al. 2009[Abdel-Aziz, M., Abuo-Rahma, D. G. & Hassan, A. A. (2009). Eur. J. Med. Chem. 44, 3480-3487.]), anti-cancer (Grosse et al., 2014[Grosse, S., Mathieu, V., Pillard, C., Massip, S., Marchivie, M., Jarry, C., Bernard, P., Kiss, R. & Guillaumet, G. (2014). Eur. J. Med. Chem. 84, 718-730.]) and anti-viral activities (Hamdy & El-Senousy, 2013[Hamdy, N. A. & El-Senousy, W. M. (2013). Acta Pol. Pharm. 70, 99-110.]) in addition to their anti-inflammatory and anti-microbial activities. Moreover, pyrazoles containing 4-substituted-1,2,4-triazole-3-thio­nes have been reported to possess anti-inflammatory activities (El-Moghazy et al., 2012[El-Moghazy, S. M., Barsoum, F. F., Abdel-Rahman, H. M. & Marzouk, A. A. (2012). Med. Chem. Res. 21, 1722-1733.]). As part of our research in this area, we report herein the synthesis and crystal structure of the title compound.

The title mol­ecule adopts a `pincer' conformation which is at least partly determined by two intra­molecular C—H⋯π(ring) inter­actions (Table 1[link] and Fig. 1[link]). The dihedral angle between the C3–C8 and N1–N3/C1/C2 rings is 81.41 (7)° while that between the latter ring and the N4/N5,C11–C13 ring is 87.05 (8)°. Pairwise N3—H3⋯N5v hydrogen bonds (Table 1[link]) form dimers which are linked into a three-dimensional network by a combination of three sets of C—H⋯S hydrogen bonds and a set of C—H⋯π(ring) inter­actions (Table 1[link] and Figs. 2[link] and 3[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C2, N4/N5/C11–C13 and C3–C8 rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8⋯Cg2 0.95 2.81 3.2544 (14) 110
C14—H14ACg3 0.98 2.79 3.6130 (17) 143
N3—H3N⋯N5i 0.878 (18) 1.978 (18) 2.8334 (17) 164.5 (16)
C15—H15C⋯N2ii 0.98 2.59 3.550 (2) 168
C9—H9BCg1ii 0.98 2.88 3.637 (2) 135
C5—H5⋯S1iii 0.95 2.93 3.824 (2) 157
C10—H10A⋯S1iv 0.99 2.93 3.747 (1) 140
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x-1, y, z; (iii) [-x+{\script{3\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}}].
[Figure 1]
Figure 1
The title mol­ecule with labelling scheme and 50% probability ellipsoids. The intra­molecular C—H⋯π(ring) inter­actions are shown as dotted lines.
[Figure 2]
Figure 2
Detail of the inter­molecular N—H⋯N (blue dotted lines) and C—H⋯S (black dotted lines) hydrogen bonds and the inter­molecular C—H⋯π(ring) (orange dotted lines) inter­actions. [Symmetry codes: (i) −1 + x, y, z; (ii) −[{1\over 2}] + x, [{1\over 2}] − y, [{1\over 2}] + 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.]
[Figure 3]
Figure 3
Packing viewed along the a axis. Inter­molecular N—H⋯N and C—H⋯S hydrogen bonds are shown, respectively, as blue and black dotted lines.

Synthesis and crystallization

A solution of 2-(2-(3,5-dimethyl-1H-pyrazol-1-yl)acet­yl)-N-p-tolyl­hydrazinecarbo­thio­amide (1.27 g; 4 mmol) in ethanol (50 ml) was added dropwise to 2 N sodium hydroxide solution (20 ml). The reaction mixture was then refluxed for 2 h, cooled, filtered and the filtrate was acidified with 2 N hydro­chloric acid solution. The separated solid was collected, washed with water and crystallized from ethanol solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C15H17N5S
Mr 299.39
Crystal system, space group Monoclinic, P21/n
Temperature (K) 150
a, b, c (Å) 7.9322 (2), 15.2415 (4), 13.6694 (4)
β (°) 106.316 (1)
V3) 1586.06 (7)
Z 4
Radiation type Cu Kα
μ (mm−1) 1.81
Crystal size (mm) 0.15 × 0.15 × 0.07
 
Data collection
Diffractometer Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction Multi-scan (SADABS; Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.82, 0.89
No. of measured, independent and observed [I > 2σ(I)] reflections 11791, 3070, 2812
Rint 0.028
(sin θ/λ)max−1) 0.618
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.091, 1.05
No. of reflections 3070
No. of parameters 191
Δρmax, Δρmin (e Å−3) 0.24, −0.21
Computer programs: APEX3 and SAINT (Bruker, 2016[Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), DIAMOND (Brandenburg & Putz, 2012[Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Structural data


Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-[(3,5-Dimethyl-1H-pyrazol-1-yl)methyl]-4-(4-methylphenyl)-4,5-dihydro-1H-1,2,4-triazole-5-thione top
Crystal data top
C15H17N5SF(000) = 632
Mr = 299.39Dx = 1.254 Mg m3
Monoclinic, P21/nCu Kα radiation, λ = 1.54178 Å
a = 7.9322 (2) ÅCell parameters from 9878 reflections
b = 15.2415 (4) Åθ = 2.9–72.4°
c = 13.6694 (4) ŵ = 1.81 mm1
β = 106.316 (1)°T = 150 K
V = 1586.06 (7) Å3Thick plate, colourless
Z = 40.15 × 0.15 × 0.07 mm
Data collection top
Bruker D8 VENTURE PHOTON 100 CMOS
diffractometer
3070 independent reflections
Radiation source: INCOATEC IµS micro-focus source2812 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.028
Detector resolution: 10.4167 pixels mm-1θmax = 72.4°, θmin = 4.5°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Bruker, 2016)
k = 1818
Tmin = 0.82, Tmax = 0.89l = 1616
11791 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0454P)2 + 0.6677P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.033(Δ/σ)max < 0.001
wR(F2) = 0.091Δρmax = 0.24 e Å3
S = 1.05Δρmin = 0.21 e Å3
3070 reflectionsExtinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
191 parametersExtinction coefficient: 0.0040 (3)
0 restraints
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
xyzUiso*/Ueq
C10.92398 (17)0.37412 (8)0.35362 (10)0.0212 (2)
C21.00943 (17)0.35248 (9)0.52192 (10)0.0212 (2)
C30.77405 (17)0.25167 (9)0.41923 (9)0.0204 (3)
C40.82341 (19)0.16998 (9)0.39224 (11)0.0268 (3)
H40.93480.16170.38050.032*
C50.7066 (2)0.10048 (10)0.38268 (12)0.0341 (4)
H50.73700.04420.36310.041*
C60.5455 (2)0.11329 (11)0.40169 (11)0.0341 (4)
H60.46730.06510.39570.041*
C70.49608 (19)0.19490 (11)0.42931 (10)0.0290 (3)
C80.61277 (17)0.26505 (9)0.43697 (10)0.0230 (3)
H80.58120.32190.45440.028*
C90.3242 (2)0.20843 (14)0.45340 (13)0.0435 (4)
H9A0.25010.15640.43270.065*
H9B0.26440.25980.41630.065*
H9C0.34610.21780.52680.065*
C101.01710 (18)0.31858 (10)0.62551 (10)0.0257 (3)
H10A1.04250.25490.62840.031*
H10B1.11390.34810.67680.031*
C110.74452 (19)0.27428 (9)0.67525 (10)0.0245 (3)
C120.6022 (2)0.32088 (10)0.68573 (11)0.0273 (3)
H120.50290.29820.70320.033*
C130.63305 (19)0.40877 (9)0.66543 (11)0.0263 (3)
C140.7851 (2)0.17859 (10)0.68567 (12)0.0327 (3)
H14A0.78840.15490.61960.049*
H14B0.69400.14820.70860.049*
H14C0.89950.16980.73570.049*
C150.5202 (2)0.48732 (11)0.66467 (15)0.0405 (4)
H15A0.57360.53880.64240.061*
H15B0.50950.49750.73350.061*
H15C0.40340.47720.61770.061*
N10.89554 (14)0.32359 (7)0.43150 (8)0.0202 (2)
N21.10763 (15)0.41591 (8)0.50617 (9)0.0250 (3)
N31.05596 (15)0.42747 (8)0.40224 (9)0.0238 (3)
H3N1.093 (2)0.4738 (12)0.3762 (13)0.029*
N40.85295 (15)0.33364 (7)0.65030 (8)0.0223 (2)
N50.78636 (15)0.41691 (7)0.64379 (9)0.0242 (3)
S10.81896 (4)0.36931 (2)0.22924 (2)0.02550 (13)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0196 (4)0.0185 (5)0.0261 (5)0.0009 (3)0.0076 (4)0.0015 (3)
C20.0196 (4)0.0185 (5)0.0261 (5)0.0009 (3)0.0076 (4)0.0015 (3)
C30.0216 (6)0.0199 (6)0.0190 (6)0.0040 (5)0.0045 (5)0.0010 (5)
C40.0271 (7)0.0236 (7)0.0307 (7)0.0008 (5)0.0099 (6)0.0023 (6)
C50.0444 (9)0.0219 (7)0.0356 (8)0.0068 (6)0.0106 (7)0.0046 (6)
C60.0377 (8)0.0338 (8)0.0283 (7)0.0171 (7)0.0052 (6)0.0003 (6)
C70.0227 (7)0.0417 (9)0.0206 (6)0.0085 (6)0.0031 (5)0.0032 (6)
C80.0209 (6)0.0272 (7)0.0200 (6)0.0003 (5)0.0042 (5)0.0013 (5)
C90.0254 (8)0.0717 (13)0.0345 (8)0.0139 (8)0.0098 (6)0.0007 (8)
C100.0222 (7)0.0287 (7)0.0245 (7)0.0012 (5)0.0037 (5)0.0025 (5)
C110.0310 (7)0.0229 (7)0.0181 (6)0.0058 (5)0.0046 (5)0.0018 (5)
C120.0311 (7)0.0281 (8)0.0249 (7)0.0085 (6)0.0114 (6)0.0027 (6)
C130.0263 (7)0.0256 (7)0.0270 (7)0.0052 (5)0.0077 (6)0.0060 (6)
C140.0397 (9)0.0235 (8)0.0328 (8)0.0026 (6)0.0069 (7)0.0069 (6)
C150.0316 (8)0.0315 (9)0.0593 (11)0.0026 (6)0.0141 (8)0.0134 (8)
N10.0187 (5)0.0188 (6)0.0232 (5)0.0019 (4)0.0062 (4)0.0005 (4)
N20.0227 (6)0.0247 (6)0.0273 (6)0.0029 (4)0.0062 (5)0.0020 (5)
N30.0254 (6)0.0202 (6)0.0272 (6)0.0047 (4)0.0094 (5)0.0004 (5)
N40.0237 (6)0.0209 (6)0.0213 (5)0.0012 (4)0.0047 (4)0.0018 (4)
N50.0253 (6)0.0198 (6)0.0267 (6)0.0026 (4)0.0059 (5)0.0008 (4)
S10.0306 (2)0.0232 (2)0.02287 (19)0.00195 (12)0.00779 (14)0.00007 (12)
Geometric parameters (Å, º) top
C1—N31.3446 (17)C9—H9C0.9800
C1—N11.3830 (17)C10—N41.4528 (18)
C1—S11.6716 (14)C10—H10A0.9900
C2—N21.2969 (18)C10—H10B0.9900
C2—N11.3821 (17)C11—N41.3562 (17)
C2—C101.4925 (18)C11—C121.375 (2)
C3—C81.3825 (19)C11—C141.492 (2)
C3—C41.3860 (19)C12—C131.403 (2)
C3—N11.4378 (16)C12—H120.9500
C4—C51.389 (2)C13—N51.3356 (19)
C4—H40.9500C13—C151.493 (2)
C5—C61.387 (2)C14—H14A0.9800
C5—H50.9500C14—H14B0.9800
C6—C71.388 (2)C14—H14C0.9800
C6—H60.9500C15—H15A0.9800
C7—C81.399 (2)C15—H15B0.9800
C7—C91.504 (2)C15—H15C0.9800
C8—H80.9500N2—N31.3749 (16)
C9—H9A0.9800N3—H3N0.877 (18)
C9—H9B0.9800N4—N51.3680 (16)
N3—C1—N1103.24 (11)C2—C10—H10B109.3
N3—C1—S1128.72 (11)H10A—C10—H10B108.0
N1—C1—S1128.04 (10)N4—C11—C12106.20 (12)
N2—C2—N1111.18 (12)N4—C11—C14122.77 (13)
N2—C2—C10123.31 (12)C12—C11—C14131.03 (13)
N1—C2—C10125.47 (12)C11—C12—C13106.16 (12)
C8—C3—C4121.58 (13)C11—C12—H12126.9
C8—C3—N1119.34 (12)C13—C12—H12126.9
C4—C3—N1119.06 (12)N5—C13—C12110.66 (13)
C3—C4—C5118.64 (14)N5—C13—C15120.36 (13)
C3—C4—H4120.7C12—C13—C15128.98 (14)
C5—C4—H4120.7C11—C14—H14A109.5
C6—C5—C4120.01 (15)C11—C14—H14B109.5
C6—C5—H5120.0H14A—C14—H14B109.5
C4—C5—H5120.0C11—C14—H14C109.5
C5—C6—C7121.50 (14)H14A—C14—H14C109.5
C5—C6—H6119.3H14B—C14—H14C109.5
C7—C6—H6119.3C13—C15—H15A109.5
C6—C7—C8118.28 (13)C13—C15—H15B109.5
C6—C7—C9121.68 (14)H15A—C15—H15B109.5
C8—C7—C9120.03 (15)C13—C15—H15C109.5
C3—C8—C7119.98 (13)H15A—C15—H15C109.5
C3—C8—H8120.0H15B—C15—H15C109.5
C7—C8—H8120.0C2—N1—C1107.70 (11)
C7—C9—H9A109.5C2—N1—C3126.55 (11)
C7—C9—H9B109.5C1—N1—C3125.71 (11)
H9A—C9—H9B109.5C2—N2—N3104.38 (11)
C7—C9—H9C109.5C1—N3—N2113.45 (11)
H9A—C9—H9C109.5C1—N3—H3N126.1 (11)
H9B—C9—H9C109.5N2—N3—H3N119.0 (11)
N4—C10—C2111.49 (11)C11—N4—N5112.00 (11)
N4—C10—H10A109.3C11—N4—C10128.80 (12)
C2—C10—H10A109.3N5—N4—C10119.10 (11)
N4—C10—H10B109.3C13—N5—N4104.98 (11)
C8—C3—C4—C50.2 (2)N3—C1—N1—C3175.76 (12)
N1—C3—C4—C5178.65 (12)S1—C1—N1—C34.15 (19)
C3—C4—C5—C61.1 (2)C8—C3—N1—C282.53 (16)
C4—C5—C6—C70.7 (2)C4—C3—N1—C295.92 (16)
C5—C6—C7—C80.5 (2)C8—C3—N1—C1100.26 (15)
C5—C6—C7—C9177.92 (14)C4—C3—N1—C181.29 (16)
C4—C3—C8—C71.0 (2)N1—C2—N2—N30.52 (15)
N1—C3—C8—C7177.44 (11)C10—C2—N2—N3178.55 (12)
C6—C7—C8—C31.3 (2)N1—C1—N3—N22.35 (15)
C9—C7—C8—C3177.12 (13)S1—C1—N3—N2177.75 (10)
N2—C2—C10—N4115.87 (14)C2—N2—N3—C11.86 (15)
N1—C2—C10—N461.87 (17)C12—C11—N4—N50.22 (15)
N4—C11—C12—C130.25 (15)C14—C11—N4—N5179.05 (12)
C14—C11—C12—C13178.93 (14)C12—C11—N4—C10176.50 (12)
C11—C12—C13—N50.21 (16)C14—C11—N4—C102.8 (2)
C11—C12—C13—C15179.17 (15)C2—C10—N4—C11121.63 (14)
N2—C2—N1—C10.89 (15)C2—C10—N4—N554.42 (16)
C10—C2—N1—C1177.09 (12)C12—C13—N5—N40.08 (15)
N2—C2—N1—C3176.74 (12)C15—C13—N5—N4179.37 (13)
C10—C2—N1—C35.3 (2)C11—N4—N5—C130.09 (14)
N3—C1—N1—C21.89 (14)C10—N4—N5—C13176.77 (11)
S1—C1—N1—C2178.20 (10)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1/C2, N4/N5/C11–C13 and C3–C8 rings, respectively.
D—H···AD—HH···AD···AD—H···A
C8—H8···Cg20.952.813.2544 (14)110
C14—H14A···Cg30.982.793.6130 (17)143
N3—H3N···N5i0.878 (18)1.978 (18)2.8334 (17)164.5 (16)
C15—H15C···N2ii0.982.593.550 (2)168
C9—H9B···Cg1ii0.982.883.637 (2)135
C5—H5···S1iii0.952.933.824 (2)157
C10—H10A···S1iv0.992.933.747 (1)140
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y, z; (iii) x+3/2, y1/2, z+1/2; (iv) x+1/2, y+1/2, z+1/2.
 

Acknowledgements

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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