Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

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| x190218
https://doi.org/10.1107/S2414314619002189

2-[3-(4-Chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]-8H-indeno­[1,2-d]thia­zole

CROSSMARK_Color_square_no_text.svg
Gamal A. El-Hiti,a* Bakr F. Abdel-Wahab,b,c Alaa Alqahtani,d Amany S. Hegazye and Benson M. Kariukie‡

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, dPharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia, and eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, UK
*Correspondence e-mail: gelhiti@ksu.edu.sa

Edited by A. J. Lough, University of Toronto, Canada (Received 31 January 2019; accepted 10 February 2019; online 22 February 2019)

The title mol­ecule, C25H17ClFN3S, contains indeno­thia­zolyl (A), pyrazolyl (B), fluoro­phenyl (C) and chloro­phenyl (D) groups. The dihedral angles between the ring planes A/B, B/C and B/D are 14.2 (1), 83.0 (1) and 6.5 (2)°, respectively. In the crystal, pairs of mol­ecules related by inversion symmetry are linked by pairwise weak C—H⋯N inter­actions, forming dimers. These dimers inter­act through π–π contacts between the thia­zolyl units [centroid-to-centroid distance = 3.826 (1) Å], forming chains along [010].

CCDC reference: 1896426

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

Structure description

Indeno­[1,2-d]thia­zoles act as histone de­acetyl­ase inhibitors (Zhou et al., 2013[Zhou, M., Ning, C., Liu, R., He, Y. & Yu, N. (2013). Bioorg. Med. Chem. Lett. 23, 3200-3203.]; Chordia et al., 2005[Chordia, M. D., Zigler, M., Murphree, L. J., Figler, H., Macdonald, T. L., Olsson, R. A. & Linden, J. (2005). J. Med. Chem. 48, 5131-5139.]). Thia­zoles and pyrazoles have various biological activities (Chhabria et al., 2016[Chhabria, M. T., Patel, S., Modi, P. & Brahmkshatriya, P. S. (2016). Curr. Top. Med. Chem. 16, 2841-2862.]; 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 report the synthesis and structure of the title compound.

The asymmetric unit consists of one mol­ecule of the title compound. The mol­ecule contains an indeno­thia­zolyl ring system (A) and pyrazolyl (B), fluoro­phenyl (C) and chloro­phenyl (D) rings (Fig. 1[link]). The twist angles between the planes through neighbouring ring pairs A/B, B/C and B/D are 14.2 (1)°, 83.0 (1)° and 6.5 (2)°, respectively. In the crystal, pairs of mol­ecules related by inversion symmetry are linked by C—H⋯N inter­actions, forming dimers in the crystal structure (Table 1[link], Fig. 2[link]). Neighbouring dimers inter­act through π–π contacts involving the thia­zolyl fragments with centroid-to-centroid distances of 3.826 (1) Å, forming chains along [010].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C16—H16⋯N1i 0.93 2.59 3.392 (3) 145
Symmetry code: (i) -x+1, -y+1, -z.
[Figure 1]
Figure 1
The mol­ecular structure of the title compound showing 50% probability ellipsoids.
[Figure 2]
Figure 2
The crystal packing viewed along the a axis showing inter­molecular contacts as dotted lines (C—H⋯N in green and π–π in red) with some hydrogen atoms omitted for clarity.

Synthesis and crystallization

The title compound was synthesized from the condensation reaction between 3-(4-chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazole-1-carbo­thio­amide (0.67 g, 2.0 mmol) and 2-bromo-2,3-di­hydro-1H-inden-1-one (1.10 g, 2.0 mmol) in anhydrous ethanol (20 ml) under reflux for 2 h. The solid obtained was recrystallized from di­methyl­formamide solution to give colourless crystals (72%), m.p. 510–511 K.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula C25H17ClFN3S
Mr 445.92
Crystal system, space group Monoclinic, P21/c
Temperature (K) 296
a, b, c (Å) 11.6975 (6), 11.0671 (5), 16.5395 (10)
β (°) 100.303 (6)
V (Å3) 2106.6 (2)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.31
Crystal size (mm) 0.44 × 0.32 × 0.06
 
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 Ltd, Yarnton, England.])
Tmin, Tmax 0.989, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections 21492, 5397, 3547
Rint 0.043
(sin θ/λ)max (Å−1) 0.703
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.129, 1.03
No. of reflections 5397
No. of parameters 280
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.25, −0.22
Computer programs: CrysAlis PRO (Rigaku OD, 2015[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, 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: 1896426

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002189/lh4044sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619002189/lh4044Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619002189/lh4044Isup3.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).

2-[3-(4-Chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]-8H-indeno[1,2-d]thiazole top
Crystal data top
C25H17ClFN3SF(000) = 920
Mr = 445.92Dx = 1.406 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.6975 (6) ÅCell parameters from 5333 reflections
b = 11.0671 (5) Åθ = 4.0–27.3°
c = 16.5395 (10) ŵ = 0.31 mm−1
β = 100.303 (6)°T = 296 K
V = 2106.6 (2) Å3Plate, colourless
Z = 40.44 × 0.32 × 0.06 mm
Data collection top
Rigaku Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas
diffractometer		3547 reflections with I > 2σ(I)
ω scansRint = 0.043
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2015)		θmax = 30.0°, θmin = 3.4°
Tmin = 0.989, Tmax = 0.998h = −15→15
21492 measured reflectionsk = −15→13
5397 independent reflectionsl = −22→22
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.129 w = 1/[σ2(Fo2) + (0.0434P)2 + 0.7878P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
5397 reflectionsΔρmax = 0.25 e Å−3
280 parametersΔρmin = −0.22 e Å−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.

Refinement. All hydrogen atoms were placed in calculated positions and refined using a riding model. Bond distances for methine and aromatic C—H H atoms were set to 0.98 Å and 0.93 Å respectively. Bond distances for methylene C—H H atoms were set to 0.97 Å and all Uiso(H) set to 1.2 times Ueq(C).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.36830 (18)−0.00576 (17)−0.10974 (13)0.0483 (5)
C20.44396 (17)0.08820 (17)−0.10383 (13)0.0462 (5)
C30.52516 (17)0.06919 (17)−0.15981 (12)0.0464 (5)
C40.49318 (18)−0.03929 (17)−0.20216 (13)0.0475 (5)
C50.3909 (2)−0.09670 (18)−0.17192 (14)0.0538 (5)
H5A0.324551−0.105536−0.2159510.065*
H5B0.411204−0.174911−0.1469430.065*
C60.61892 (19)0.13560 (19)−0.17651 (14)0.0544 (5)
H60.6417140.206470−0.1479140.065*
C70.6778 (2)0.0942 (2)−0.23659 (15)0.0624 (6)
H70.7408340.137899−0.2481920.075*
C80.6448 (2)−0.0103 (2)−0.27944 (15)0.0624 (6)
H80.684815−0.035674−0.3201970.075*
C90.5523 (2)−0.0782 (2)−0.26226 (14)0.0575 (6)
H90.530384−0.149161−0.2910190.069*
C100.34436 (18)0.15028 (16)−0.01316 (13)0.0471 (5)
C110.35404 (19)0.33553 (17)0.07738 (13)0.0514 (5)
H110.4391640.3339250.0869550.062*
C120.3099 (2)0.33867 (18)0.15953 (13)0.0540 (5)
H12A0.3716660.3204980.2053300.065*
H12B0.2764370.4166570.1685310.065*
C130.21881 (18)0.24094 (17)0.14765 (13)0.0497 (5)
C140.30859 (17)0.44092 (17)0.02312 (12)0.0448 (4)
C150.37269 (18)0.54709 (18)0.02780 (13)0.0483 (5)
H150.4461410.5494700.0604770.058*
C160.32965 (19)0.64896 (18)−0.01498 (14)0.0530 (5)
H160.3731570.719698−0.0117240.064*
C170.2220 (2)0.6434 (2)−0.06206 (14)0.0569 (6)
C180.1550 (2)0.5415 (2)−0.06839 (15)0.0623 (6)
H180.0814320.540603−0.1009260.075*
C190.19912 (19)0.4400 (2)−0.02540 (14)0.0553 (5)
H190.1546500.369904−0.0290610.066*
C200.13608 (18)0.21879 (18)0.20216 (13)0.0495 (5)
C210.1378 (2)0.2885 (2)0.27216 (14)0.0600 (6)
H210.1934190.3488730.2847040.072*
C220.0585 (2)0.2697 (2)0.32356 (15)0.0647 (6)
H220.0598980.3177080.3698710.078*
C24−0.0221 (2)0.1798 (2)0.30554 (15)0.0591 (6)
C25−0.0244 (2)0.1081 (2)0.23778 (17)0.0673 (6)
H25−0.0788250.0462780.2266940.081*
C260.0535 (2)0.1274 (2)0.18630 (15)0.0632 (6)
H260.0511520.0787060.1401850.076*
N10.43084 (15)0.17969 (14)−0.04911 (11)0.0488 (4)
N20.30655 (17)0.21900 (15)0.04455 (12)0.0582 (5)
N30.22147 (16)0.17424 (15)0.08447 (12)0.0529 (4)
F10.17949 (14)0.74318 (13)−0.10484 (10)0.0883 (5)
Cl1−0.12023 (6)0.15339 (7)0.37082 (5)0.0860 (2)
S10.27382 (5)0.01232 (4)−0.04205 (3)0.05072 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0528 (12)0.0401 (10)0.0530 (12)0.0004 (9)0.0120 (10)−0.0012 (9)
C20.0492 (11)0.0405 (10)0.0490 (11)0.0013 (8)0.0090 (9)0.0003 (9)
C30.0492 (11)0.0431 (10)0.0466 (11)0.0056 (9)0.0080 (9)0.0056 (9)
C40.0545 (12)0.0413 (10)0.0464 (11)0.0058 (9)0.0084 (9)0.0033 (9)
C50.0631 (13)0.0428 (11)0.0560 (13)0.0009 (10)0.0123 (11)−0.0032 (9)
C60.0576 (13)0.0480 (11)0.0594 (14)−0.0001 (10)0.0154 (11)0.0005 (10)
C70.0642 (14)0.0611 (14)0.0668 (15)0.0035 (11)0.0247 (12)0.0086 (12)
C80.0743 (16)0.0621 (14)0.0560 (14)0.0138 (12)0.0260 (12)0.0073 (11)
C90.0729 (15)0.0490 (12)0.0520 (13)0.0080 (11)0.0153 (12)−0.0003 (10)
C100.0531 (12)0.0372 (9)0.0520 (12)−0.0001 (8)0.0122 (10)−0.0003 (9)
C110.0544 (12)0.0423 (10)0.0591 (13)−0.0048 (9)0.0149 (10)−0.0069 (9)
C120.0653 (14)0.0468 (11)0.0499 (12)−0.0032 (10)0.0106 (11)−0.0019 (9)
C130.0553 (12)0.0419 (10)0.0520 (12)0.0014 (9)0.0103 (10)−0.0012 (9)
C140.0474 (11)0.0453 (10)0.0441 (11)−0.0066 (8)0.0148 (9)−0.0082 (8)
C150.0460 (11)0.0515 (11)0.0489 (12)−0.0086 (9)0.0128 (9)−0.0069 (9)
C160.0599 (13)0.0466 (11)0.0557 (13)−0.0113 (10)0.0191 (11)−0.0031 (10)
C170.0667 (14)0.0527 (12)0.0525 (13)0.0027 (11)0.0141 (11)0.0022 (10)
C180.0561 (13)0.0701 (15)0.0568 (14)−0.0075 (11)−0.0007 (11)−0.0016 (12)
C190.0555 (12)0.0529 (12)0.0574 (13)−0.0152 (10)0.0097 (11)−0.0070 (10)
C200.0552 (12)0.0435 (10)0.0503 (12)0.0047 (9)0.0108 (10)0.0026 (9)
C210.0714 (15)0.0521 (12)0.0591 (14)−0.0044 (11)0.0186 (12)−0.0020 (11)
C220.0825 (17)0.0596 (14)0.0559 (14)0.0024 (12)0.0231 (13)−0.0005 (11)
C240.0531 (13)0.0668 (14)0.0605 (14)0.0118 (11)0.0187 (11)0.0170 (12)
C250.0587 (14)0.0705 (15)0.0743 (17)−0.0080 (12)0.0163 (13)0.0031 (13)
C260.0623 (14)0.0668 (14)0.0622 (15)−0.0082 (11)0.0164 (12)−0.0100 (12)
N10.0522 (10)0.0406 (8)0.0554 (10)−0.0033 (7)0.0143 (8)−0.0059 (7)
N20.0699 (12)0.0414 (9)0.0705 (12)−0.0104 (8)0.0324 (10)−0.0115 (8)
N30.0598 (11)0.0432 (9)0.0601 (11)−0.0049 (8)0.0224 (9)−0.0049 (8)
F10.0987 (11)0.0689 (9)0.0919 (12)0.0080 (8)0.0023 (9)0.0216 (8)
Cl10.0753 (4)0.1069 (6)0.0848 (5)0.0073 (4)0.0388 (4)0.0210 (4)
S10.0565 (3)0.0401 (3)0.0580 (3)−0.0045 (2)0.0169 (3)−0.0028 (2)
Geometric parameters (Å, º) top
C1—C21.358 (3)C12—H12B0.9700
C1—C51.496 (3)C13—N31.284 (3)
C1—S11.720 (2)C13—C201.457 (3)
C2—N11.385 (3)C14—C191.384 (3)
C2—C31.455 (3)C14—C151.389 (3)
C3—C61.388 (3)C15—C161.378 (3)
C3—C41.406 (3)C15—H150.9300
C4—C91.377 (3)C16—C171.359 (3)
C4—C51.516 (3)C16—H160.9300
C5—H5A0.9700C17—F11.357 (3)
C5—H5B0.9700C17—C181.366 (3)
C6—C71.384 (3)C18—C191.379 (3)
C6—H60.9300C18—H180.9300
C7—C81.375 (3)C19—H190.9300
C7—H70.9300C20—C211.388 (3)
C8—C91.389 (3)C20—C261.391 (3)
C8—H80.9300C21—C221.382 (3)
C9—H90.9300C21—H210.9300
C10—N11.303 (3)C22—C241.367 (3)
C10—N21.355 (3)C22—H220.9300
C10—S11.7605 (19)C24—C251.369 (3)
C11—N21.469 (2)C24—Cl11.735 (2)
C11—C141.509 (3)C25—C261.371 (3)
C11—C121.538 (3)C25—H250.9300
C11—H110.9800C26—H260.9300
C12—C131.506 (3)N2—N31.381 (2)
C12—H12A0.9700
C2—C1—C5111.81 (19)N3—C13—C20121.49 (19)
C2—C1—S1110.52 (15)N3—C13—C12113.55 (19)
C5—C1—S1137.66 (16)C20—C13—C12124.95 (18)
C1—C2—N1117.39 (19)C19—C14—C15118.22 (19)
C1—C2—C3109.55 (18)C19—C14—C11122.01 (18)
N1—C2—C3133.06 (18)C15—C14—C11119.43 (18)
C6—C3—C4120.1 (2)C16—C15—C14121.32 (19)
C6—C3—C2132.74 (19)C16—C15—H15119.3
C4—C3—C2107.13 (17)C14—C15—H15119.3
C9—C4—C3120.2 (2)C17—C16—C15118.24 (19)
C9—C4—C5129.37 (19)C17—C16—H16120.9
C3—C4—C5110.41 (18)C15—C16—H16120.9
C1—C5—C4101.07 (17)F1—C17—C16118.5 (2)
C1—C5—H5A111.6F1—C17—C18118.7 (2)
C4—C5—H5A111.6C16—C17—C18122.8 (2)
C1—C5—H5B111.6C17—C18—C19118.4 (2)
C4—C5—H5B111.6C17—C18—H18120.8
H5A—C5—H5B109.4C19—C18—H18120.8
C7—C6—C3118.7 (2)C18—C19—C14121.0 (2)
C7—C6—H6120.7C18—C19—H19119.5
C3—C6—H6120.7C14—C19—H19119.5
C8—C7—C6121.2 (2)C21—C20—C26117.9 (2)
C8—C7—H7119.4C21—C20—C13120.70 (19)
C6—C7—H7119.4C26—C20—C13121.4 (2)
C7—C8—C9120.5 (2)C22—C21—C20121.2 (2)
C7—C8—H8119.8C22—C21—H21119.4
C9—C8—H8119.8C20—C21—H21119.4
C4—C9—C8119.3 (2)C24—C22—C21119.2 (2)
C4—C9—H9120.4C24—C22—H22120.4
C8—C9—H9120.4C21—C22—H22120.4
N1—C10—N2123.99 (18)C22—C24—C25120.8 (2)
N1—C10—S1117.21 (15)C22—C24—Cl1119.6 (2)
N2—C10—S1118.80 (16)C25—C24—Cl1119.6 (2)
N2—C11—C14112.88 (18)C24—C25—C26120.0 (2)
N2—C11—C12100.47 (16)C24—C25—H25120.0
C14—C11—C12111.69 (17)C26—C25—H25120.0
N2—C11—H11110.5C25—C26—C20120.8 (2)
C14—C11—H11110.5C25—C26—H26119.6
C12—C11—H11110.5C20—C26—H26119.6
C13—C12—C11102.13 (16)C10—N1—C2107.54 (16)
C13—C12—H12A111.3C10—N2—N3119.31 (16)
C11—C12—H12A111.3C10—N2—C11127.12 (18)
C13—C12—H12B111.3N3—N2—C11113.29 (17)
C11—C12—H12B111.3C13—N3—N2107.89 (17)
H12A—C12—H12B109.2C1—S1—C1087.31 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N1i0.932.593.392 (3)145
Symmetry code: (i) −x+1, −y+1, −z.
 

Footnotes

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

Acknowledgements

The authors thank Umm Al-Qura and Cardiff Universities for their continuing support.

Funding information

Funding for this research was provided by: Deanship of Scientific Research at Umm Al-Qura University (award No. 17-MED-1-03-0007).

References

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 citationChordia, M. D., Zigler, M., Murphree, L. J., Figler, H., Macdonald, T. L., Olsson, R. A. & Linden, J. (2005). J. Med. Chem. 48, 5131–5139.  CrossRef 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 citationRigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, 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
 First citationZhou, M., Ning, C., Liu, R., He, Y. & Yu, N. (2013). Bioorg. Med. Chem. Lett. 23, 3200–3203.  CrossRef CAS 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.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 4| Part 2| February 2019| x190218
https://doi.org/10.1107/S2414314619002189
Follow IUCr Journals
Sign up for e-alerts
E-alerts
Follow IUCr on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS