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

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 4| Part 2| February 2019| x190211
https://doi.org/10.1107/S2414314619002116

5-[(4-Chloro­phen­yl)diazen­yl]-2-[5-(4-fluoro­phen­yl)-3-(furan-2-yl)-4,5-di­hydro-1H-pyrazol-1-yl]-4-methyl­thia­zole

CROSSMARK_Color_square_no_text.svg
Gamal A El-Hiti,a* Bakr F. Abdel-Wahab,b,c Emad Yousif,d Mohammad Hayal Alotaibi,e Amany S. Hegazyf and Benson M. Kariukif‡

aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, dDepartment of Chemistry, College of Science, Al-Nahrain University, Baghdad 64021, Iraq, eNational Center for Petrochemicals Technology, King Abdulaziz City for Science and Technology, PO Box 6086, Riyadh 11442, Saudi Arabia, and fSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 5 February 2019; accepted 6 February 2019; online 12 February 2019)

The title compound, C23H17ClFN5OS, comprises fluoro­phenyl (A), furanyl (B), pyrazolyl (C), methyl­thiazoyl (D) and chloro­phenyl (E) rings. The B–C–D–E linked ring system is close to planar with the dihedral angles B/C, C/D and D/E being 7.6 (1), 3.4 (1) and 8.4 (1)°, respectively. The fluoro­phenyl group is almost perpendicular to the pyrazoyl ring, as indicated by an A/C twist angle of 79.4 (1)°. In the crystal, inversion dimers linked by pairs of C—H⋯S contacts are observed.

CCDC reference: 1895864

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

Structure description

Thia­zoles are of importance in medicinal chemistry as they have various biological activities (Kashyap et al., 2012[Kashyap, S. J., Garg, V. K., Sharma, P. K., Kumar, N., Dudhe, R. & Gupta, J. K. (2012). Med. Chem. Res. 21, 2123-2132.]) and occur in natural products (Chhabria et al., 2016[Chhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841-2862.]). Pyrazoles have a broad spectrum of biological activities (Faria et al., 2017[Faria, J. V., Vegi, P. F., Miguita, A. G. C., Dos Santos, M. S., Boechat, N. & Bernardino, A. M. R. (2017). Bioorg. Med. Chem. 25, 5891-5903.]). As part of our studies in these areas, we now describe the structure of the title compound.

The asymmetric unit consists of one mol­ecule of the title compound and comprises fluoro­phenyl (A), furanyl (B), pyrazolyl (C), methyl­thiazoyl (D) and chloro­phenyl (E) rings (Fig. 1[link]). The B–C–D–E linked ring system is close to planar with the B/C, C/D and D/E angles between neighbouring rings being 7.6 (1), 3.4 (1) and 8.4 (1)°, respectively. The fluoro­phenyl group (A) is almost perpendicular to the B–E system as indicated by an A/C twist angle of 79.4 (1)°. In the crystal, inversion dimers linked by pairs of C—H⋯S bonds (Table 1[link]) generate R22(18) loops, which are stacked in the [100] direction (Fig. 2[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C13—H13⋯S2i 0.93 2.85 3.612 (2) 140
Symmetry code: (i) -x-1, -y, -z.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 50% displacement ellipsoids.
[Figure 2]
Figure 2
A view of the crystal structure down [100] showing inter­molecular short contacts as dotted lines.

Synthesis and crystallization

The title compound was synthesized by the condensation of 5-(4-fluoro­phen­yl)-3-(furan-2-yl)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide with N′-(4-chloro­phen­yl)-2-oxo­propane­hydrazonoyl chloride in ethanol containing catalytic amount of tri­ethyl­amine as previously reported (Abdel-Wahab et al., 2013[Abdel-Wahab, B. F., Sediek, A., Mohamed, H. A. & Awad, G. E. A. (2013). Lett. Drug. Des. Discov. 10, 111-118.]). The product was recrystallized from di­methyl­formamide solution to give colourless crystals (74%), m.p. 227–228°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C23H17ClFN5OS
Mr 465.92
Crystal system, space group Monoclinic, P21/c
Temperature (K) 298
a, b, c (Å) 5.2879 (3), 26.3742 (10), 15.7872 (7)
β (°) 98.293 (4)
V (Å3) 2178.72 (18)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.31
Crystal size (mm) 0.49 × 0.16 × 0.15
 
Data collection
Diffractometer Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.993, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections 21057, 5523, 4143
Rint 0.028
(sin θ/λ)max (Å−1) 0.697
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.113, 1.04
No. of reflections 5523
No. of parameters 290
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.16, −0.31
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CHEMDRAW Ultra (Cambridge Soft, 2001[Cambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.]).

Structural data

CCDC reference: 1895864

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002116/hb4284sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002116/hb4284Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002116/hb4284Isup3.cml

checkCIF report


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: CHEMDRAW Ultra (Cambridge Soft, 2001).

5-[(4-Chlorophenyl)diazenyl]-2-[5-(4-fluorophenyl)-3-(furan-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-methylthiazole top
Crystal data top
C23H17ClFN5OSF(000) = 960
Mr = 465.92Dx = 1.420 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 5.2879 (3) ÅCell parameters from 6690 reflections
b = 26.3742 (10) Åθ = 4.2–28.8°
c = 15.7872 (7) ŵ = 0.31 mm−1
β = 98.293 (4)°T = 298 K
V = 2178.72 (18) Å3Needle, colourless
Z = 40.49 × 0.16 × 0.14 mm
Data collection top
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
diffractometer		4143 reflections with I > 2σ(I)
ω scansRint = 0.028
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2015)		θmax = 29.7°, θmin = 3.5°
Tmin = 0.993, Tmax = 0.997h = −6→6
21057 measured reflectionsk = −33→36
5523 independent reflectionsl = −18→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0435P)2 + 0.7096P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5523 reflectionsΔρmax = 0.16 e Å−3
290 parametersΔρmin = −0.31 e Å−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.

Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Bond distances for aromatic, methine and methylene C—H hydrogen atoms were set to 0.93 Å, 0.98 Å and 0.93 Å, respectively and their Uiso values set to 1.2 times Ueq(C). Bond distances for methyl C—H hydrogen atoms were set to 0.96 Å and their Uiso set to 1.5 times Ueq(C) with the group free to rotate about the C—C bond.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0781 (5)0.26438 (8)0.25920 (13)0.0626 (6)
C2−0.0593 (4)0.22058 (9)0.25800 (12)0.0632 (6)
H2−0.1881070.2169920.2919210.076*
C3−0.0025 (4)0.18144 (8)0.20494 (11)0.0508 (4)
H3−0.0949470.1513510.2027360.061*
C40.1904 (3)0.18705 (6)0.15553 (10)0.0385 (3)
C50.3267 (4)0.23211 (6)0.15976 (11)0.0465 (4)
H50.4581230.2359500.1269870.056*
C60.2705 (5)0.27143 (7)0.21185 (13)0.0594 (5)
H60.3612950.3017220.2144160.071*
C70.2489 (3)0.14657 (6)0.09325 (11)0.0414 (4)
H70.4278710.1488750.0840200.050*
C80.0710 (4)0.14838 (6)0.00674 (11)0.0458 (4)
H8A−0.0308110.1791170.0013920.055*
H8B0.1675530.146253−0.0409170.055*
C9−0.0937 (3)0.10222 (6)0.01124 (10)0.0406 (4)
C10−0.3123 (4)0.09025 (6)−0.05042 (11)0.0431 (4)
C11−0.4169 (4)0.11166 (7)−0.12524 (11)0.0510 (4)
H11−0.3588380.140346−0.1507840.061*
C12−0.6331 (4)0.08164 (8)−0.15704 (12)0.0559 (5)
H12−0.7438480.086687−0.2076900.067*
C13−0.6459 (4)0.04478 (8)−0.09992 (13)0.0568 (5)
H13−0.7707050.019689−0.1047600.068*
C140.3140 (3)0.07128 (6)0.19213 (11)0.0413 (4)
C150.5955 (4)0.05794 (7)0.30614 (11)0.0453 (4)
C160.4562 (4)0.01408 (6)0.30647 (11)0.0451 (4)
C170.8202 (4)0.07168 (8)0.37081 (13)0.0588 (5)
H17A0.9636040.0794460.3421090.088*
H17B0.8624430.0436750.4090910.088*
H17C0.7787700.1007330.4027700.088*
C180.3905 (4)−0.10285 (7)0.40559 (11)0.0457 (4)
C190.6009 (4)−0.10844 (8)0.46822 (13)0.0598 (5)
H190.722638−0.0827980.4770580.072*
C200.6311 (4)−0.15181 (8)0.51757 (13)0.0628 (6)
H200.772774−0.1555800.5594250.075*
C210.4493 (4)−0.18944 (7)0.50416 (11)0.0475 (4)
C220.2386 (4)−0.18456 (7)0.44334 (12)0.0565 (5)
H220.116268−0.2101000.4353020.068*
C230.2105 (4)−0.14106 (7)0.39398 (13)0.0563 (5)
H230.068133−0.1375040.3523400.068*
N10.1930 (3)0.09521 (5)0.12251 (9)0.0466 (4)
N2−0.0195 (3)0.07306 (5)0.07564 (9)0.0444 (3)
N30.5145 (3)0.09084 (5)0.24081 (9)0.0452 (3)
N40.5021 (3)−0.02481 (6)0.36380 (9)0.0480 (4)
N50.3409 (3)−0.06088 (6)0.34945 (10)0.0503 (4)
F10.0203 (4)0.30294 (6)0.31041 (9)0.1010 (6)
S20.20523 (9)0.01261 (2)0.22069 (3)0.04565 (13)
Cl10.49098 (13)−0.24529 (2)0.56357 (3)0.07087 (18)
O1−0.4519 (3)0.04886 (5)−0.03373 (8)0.0550 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0723 (15)0.0617 (12)0.0474 (10)0.0251 (11)−0.0127 (10)−0.0170 (9)
C20.0544 (13)0.0884 (16)0.0475 (10)0.0187 (11)0.0095 (9)−0.0047 (10)
C30.0451 (11)0.0570 (11)0.0504 (10)−0.0036 (8)0.0076 (8)−0.0034 (8)
C40.0371 (9)0.0372 (8)0.0398 (8)−0.0012 (6)0.0012 (6)0.0004 (6)
C50.0482 (11)0.0399 (9)0.0491 (9)−0.0048 (7)−0.0007 (8)0.0001 (7)
C60.0702 (15)0.0404 (10)0.0604 (12)0.0013 (9)−0.0152 (10)−0.0079 (8)
C70.0424 (10)0.0352 (8)0.0473 (9)−0.0052 (7)0.0087 (7)−0.0015 (7)
C80.0553 (11)0.0403 (9)0.0417 (9)−0.0062 (8)0.0071 (8)−0.0021 (7)
C90.0450 (10)0.0357 (8)0.0416 (8)−0.0002 (7)0.0078 (7)−0.0031 (6)
C100.0469 (10)0.0380 (8)0.0445 (9)−0.0023 (7)0.0073 (7)−0.0038 (7)
C110.0572 (12)0.0473 (10)0.0472 (9)0.0034 (8)0.0035 (8)0.0022 (8)
C120.0574 (13)0.0578 (11)0.0486 (10)0.0084 (9)−0.0050 (9)−0.0065 (8)
C130.0500 (12)0.0548 (11)0.0613 (11)−0.0068 (9)−0.0066 (9)−0.0083 (9)
C140.0432 (10)0.0344 (8)0.0460 (9)0.0005 (7)0.0048 (7)−0.0042 (7)
C150.0430 (10)0.0462 (9)0.0460 (9)0.0013 (7)0.0038 (7)−0.0081 (7)
C160.0466 (10)0.0436 (9)0.0434 (9)0.0026 (7)0.0007 (7)−0.0034 (7)
C170.0512 (12)0.0675 (13)0.0543 (11)−0.0070 (10)−0.0043 (9)−0.0089 (9)
C180.0461 (11)0.0468 (9)0.0428 (9)0.0037 (8)0.0013 (7)0.0001 (7)
C190.0511 (12)0.0591 (12)0.0647 (12)−0.0075 (9)−0.0071 (9)0.0090 (9)
C200.0536 (13)0.0695 (13)0.0588 (11)−0.0006 (10)−0.0136 (9)0.0128 (10)
C210.0543 (12)0.0478 (9)0.0399 (8)0.0058 (8)0.0054 (8)0.0036 (7)
C220.0565 (13)0.0495 (10)0.0592 (11)−0.0059 (9)−0.0066 (9)0.0042 (8)
C230.0532 (12)0.0534 (11)0.0559 (11)−0.0018 (9)−0.0138 (9)0.0042 (8)
N10.0522 (9)0.0332 (7)0.0506 (8)−0.0070 (6)−0.0060 (7)0.0001 (6)
N20.0472 (9)0.0367 (7)0.0469 (8)−0.0040 (6)−0.0011 (6)−0.0018 (6)
N30.0457 (9)0.0403 (7)0.0485 (8)−0.0033 (6)0.0024 (6)−0.0046 (6)
N40.0510 (10)0.0463 (8)0.0456 (8)0.0020 (7)0.0030 (7)−0.0001 (6)
N50.0530 (10)0.0462 (8)0.0493 (8)0.0020 (7)−0.0006 (7)0.0027 (6)
F10.1302 (14)0.0924 (10)0.0740 (9)0.0464 (10)−0.0072 (9)−0.0408 (8)
S20.0486 (3)0.0353 (2)0.0500 (2)−0.00246 (17)−0.00321 (19)−0.00071 (16)
Cl10.0867 (4)0.0649 (3)0.0580 (3)0.0043 (3)0.0002 (3)0.0203 (2)
O10.0565 (9)0.0499 (7)0.0546 (7)−0.0141 (6)−0.0052 (6)0.0049 (6)
Geometric parameters (Å, º) top
C1—C61.359 (3)C13—H130.9300
C1—F11.361 (2)C14—N31.321 (2)
C1—C21.363 (3)C14—N11.346 (2)
C2—C31.389 (3)C14—S21.7330 (17)
C2—H20.9300C15—N31.369 (2)
C3—C41.379 (2)C15—C161.372 (3)
C3—H30.9300C15—C171.495 (3)
C4—C51.386 (2)C16—N41.366 (2)
C4—C71.513 (2)C16—S21.7546 (18)
C5—C61.382 (3)C17—H17A0.9600
C5—H50.9300C17—H17B0.9600
C6—H60.9300C17—H17C0.9600
C7—N11.475 (2)C18—C231.380 (3)
C7—C81.543 (2)C18—C191.386 (3)
C7—H70.9800C18—N51.419 (2)
C8—C91.504 (2)C19—C201.380 (3)
C8—H8A0.9700C19—H190.9300
C8—H8B0.9700C20—C211.377 (3)
C9—N21.290 (2)C20—H200.9300
C9—C101.435 (2)C21—C221.368 (3)
C10—C111.353 (2)C21—Cl11.7432 (18)
C10—O11.365 (2)C22—C231.383 (3)
C11—C121.422 (3)C22—H220.9300
C11—H110.9300C23—H230.9300
C12—C131.334 (3)N1—N21.3823 (19)
C12—H120.9300N4—N51.276 (2)
C13—O11.359 (2)
C6—C1—F1118.3 (2)O1—C13—H13124.6
C6—C1—C2123.24 (18)N3—C14—N1122.60 (15)
F1—C1—C2118.4 (2)N3—C14—S2117.77 (13)
C1—C2—C3118.5 (2)N1—C14—S2119.63 (13)
C1—C2—H2120.8N3—C15—C16115.32 (16)
C3—C2—H2120.8N3—C15—C17119.51 (16)
C4—C3—C2120.21 (19)C16—C15—C17125.17 (17)
C4—C3—H3119.9N4—C16—C15126.26 (17)
C2—C3—H3119.9N4—C16—S2122.47 (14)
C3—C4—C5119.12 (16)C15—C16—S2111.26 (13)
C3—C4—C7121.94 (15)C15—C17—H17A109.5
C5—C4—C7118.85 (15)C15—C17—H17B109.5
C6—C5—C4121.13 (19)H17A—C17—H17B109.5
C6—C5—H5119.4C15—C17—H17C109.5
C4—C5—H5119.4H17A—C17—H17C109.5
C1—C6—C5117.82 (19)H17B—C17—H17C109.5
C1—C6—H6121.1C23—C18—C19118.99 (17)
C5—C6—H6121.1C23—C18—N5115.16 (16)
N1—C7—C4112.05 (14)C19—C18—N5125.85 (17)
N1—C7—C8100.45 (13)C20—C19—C18120.42 (19)
C4—C7—C8113.43 (14)C20—C19—H19119.8
N1—C7—H7110.2C18—C19—H19119.8
C4—C7—H7110.2C21—C20—C19119.30 (18)
C8—C7—H7110.2C21—C20—H20120.4
C9—C8—C7102.49 (13)C19—C20—H20120.4
C9—C8—H8A111.3C22—C21—C20121.34 (17)
C7—C8—H8A111.3C22—C21—Cl1118.96 (15)
C9—C8—H8B111.3C20—C21—Cl1119.67 (15)
C7—C8—H8B111.3C21—C22—C23118.96 (18)
H8A—C8—H8B109.2C21—C22—H22120.5
N2—C9—C10121.82 (15)C23—C22—H22120.5
N2—C9—C8114.04 (15)C18—C23—C22120.99 (18)
C10—C9—C8124.13 (15)C18—C23—H23119.5
C11—C10—O1109.75 (16)C22—C23—H23119.5
C11—C10—C9133.48 (17)C14—N1—N2119.53 (14)
O1—C10—C9116.77 (15)C14—N1—C7126.37 (14)
C10—C11—C12106.40 (17)N2—N1—C7113.86 (13)
C10—C11—H11126.8C9—N2—N1107.54 (14)
C12—C11—H11126.8C14—N3—C15109.17 (14)
C13—C12—C11106.48 (17)N5—N4—C16113.09 (15)
C13—C12—H12126.8N4—N5—C18114.36 (15)
C11—C12—H12126.8C14—S2—C1686.48 (8)
C12—C13—O1110.85 (17)C13—O1—C10106.51 (14)
C12—C13—H13124.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···S2i0.932.853.612 (2)140
Symmetry code: (i) −x−1, −y, −z.
 

Footnotes

‡Additional correspondence author: e-mail kariukib@cardiff.ac.uk.

Acknowledgements

The authors thank King Saud and Cardiff Universities for continuous support.

Funding information

Funding for this research was provided by: King Abdulaziz City for Science and Technology (KACST), Saudi Arabia (award No. 020-0180).

References

First citationAbdel-Wahab, B. F., Sediek, A., Mohamed, H. A. & Awad, G. E. A. (2013). Lett. Drug. Des. Discov. 10, 111–118.  CAS Google Scholar
 First citationCambridge Soft (2001). CHEMDRAW Ultra. Cambridge Soft Corporation, Cambridge, Massachusetts, USA.  Google Scholar
 First citationChhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841–2862.  CAS Google Scholar
 First citationFaria, J. V., Vegi, P. F., Miguita, A. G. C., Dos Santos, M. S., Boechat, N. & Bernardino, A. M. R. (2017). Bioorg. Med. Chem. 25, 5891–5903.  CrossRef CAS Google Scholar
 First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationKashyap, S. J., Garg, V. K., Sharma, P. K., Kumar, N., Dudhe, R. & Gupta, J. K. (2012). Med. Chem. Res. 21, 2123–2132.  CrossRef CAS Google Scholar
 First citationRigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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ISSN: 2414-3146
Volume 4| Part 2| February 2019| x190211
https://doi.org/10.1107/S2414314619002116
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