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

Journal logoIUCrDATA
ISSN: 2414-3146

Bis(4,6-di-tert-butyl-2-{N-[4-(di­ethyl­amino)­phen­yl]carboximido­yl}phenolato)cobalt(II)

CROSSMARK_Color_square_no_text.svg

aDepartment of Chemistry, Vaigai College of Engineering, Madurai 625122, Tamil Nadu, India, bDepartment of Chemistry, University of Pitesti, Pitesti 11040, Romania, cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and dPG & Research Department of Chemistry, Chikkanna Government Arts College, Tiruppur 641 602, Tamil Nadu, India
*Correspondence e-mail: chakkaravarthi_2005@yahoo.com, rajagopal18@yahoo.com

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 23 May 2017; accepted 26 May 2017; online 2 June 2017)

In the title complex, [Co(C25H35N2O)2], the cobalt(II) atom has a distorted tetra­hedral geometry provided by pairs of O and N atoms. The dihedral angles between the benzene rings of the same ligand are 52.39 (9) and 34.96 (9)°. The mol­ecular structure is stabilized by weak intra­molecular C—H⋯O hydrogen bonds. The crystal packing is stabilized mainly by van der Waals forces. The structure contains a solvent-accessible void of 276 Å3 which was treated using the SQUEEZE routine from PLATON [Spek (2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]). Acta Cryst. C71, 9–18]. The methyl C atoms of the tert-butyl groups are rotationally disordered, with site occupancies of 0.802 (3) and 0.548 (9) for the major components and 0.198 (3) and 0.452 (9) for the minor components.

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

Structure description

In our continuing work on the development of new N- and O-chelating ligands able to play a key role in the coordination of metals at the active sites of numerous metallobimolecules (Nair et al., 2006[Nair, B., Shah, A., Baluja, S. & Chanda, S. (2006). J. Serb. Chem. Soc. 71, 733-744.]), we herein report on the synthesis and the crystal structure of the title compound (Fig. 1[link]). The cobalt(II) atom is coordinated in a distorted tetra­hedral geometry by two O and two N atoms. The Co—O and Co—N bond lengths [Co1—O1 = 1.8844 (18), Co1—O2 = 1.8867 (17), Co1—N1 = 20 1.978 (2) and Co1—N2 = 1.971 (2) Å] are similar to those reported in related structures (Adam et al., 1997[Adam, K. R., Anderson, P. A., Astley, T., Atkinson, I. M., Charnock, J. M., Garner, C. D., Gulbis, J. M., Hambley, T. W., Hitchman, M. A., Keene, F. R. & Tiekink, E. R. T. (1997). J. Chem. Soc. Dalton Trans. pp. 519-530.]; Chen et al., 2014[Chen, Y. M., Gao, Q., Zhang, H. F., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2014). Polyhedron, 71, 91-98.], 2015[Chen, Y. M., Gao, Q., Chen, W. Q., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2015). Chem. Asian J. 10, 411-421.]). Within the same ligand, the dihedral angles formed by the benzene rings are 52.39 (9) and 34.96 (9)°. The mol­ecular structure is stabilized by weak C—H⋯O hydrogen bonds (Table 1[link]). The crystal packing is mainly stabilized by van der Waals forces.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8C⋯O2 0.96 2.31 2.936 (4) 123
C9—H9C⋯O2 0.96 2.35 2.987 (4) 123
C33—H33A⋯O1 0.96 2.34 2.980 (4) 123
C34—H34A⋯O1 0.96 2.31 2.955 (4) 124
[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with the atom labelling and 30% probability displacement ellipsoids.

Synthesis and crystallization

To a solution of the Schiff base (1 mmol) in 10 ml methanol was added a solution of Co(AcO)2·H2O (0.5 mmol) in 10 ml ethanol. The resulting mixture was refluxed for 4–6 h and then cooled to room temperature. The precipitate obtained was filtered, washed in ice-cold ethanol and dried in vacuo. X-ray quality crystals were grown by layering a CHCl3 solution (3 ml) of the compound with CH3CN (5 ml).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The methyl C atoms of the tert-butyl groups are rotationally disordered, with site occupancies of 0.802 (3) and 0.548 (9) for the major components (C12, C13, C14 and C37A, C38A, C39A), and 0.198 (3) and 0.452 (9) for the minor components (C12A, C13A, C14A and C37, C38, C39). The C—C bond lengths involving the disordered atoms were restrained to 1.50 (1) Å. SIMU, SADI and DELU restraints were also applied. The structure contains a solvent-accessible void which was treated using the SQUEEZE routine from PLATON (Spek, 2015[Spek, A. L. (2015). Acta Cryst. C71, 9-18.]).

Table 2
Experimental details

Crystal data
Chemical formula [Co(C25H35N2O)2]
Mr 818.03
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 295
a, b, c (Å) 11.9460 (1), 13.2180 (2), 17.4340 (2)
α, β, γ (°) 109.348 (1), 96.350 (1), 98.881 (2)
V3) 2527.33 (6)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.38
Crystal size (mm) 0.28 × 0.24 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.851, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections 38553, 8091, 5894
Rint 0.045
(sin θ/λ)max−1) 0.579
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.146, 1.12
No. of reflections 8091
No. of parameters 592
No. of restraints 105
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.43, −0.36
Computer programs: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. A71, 3-8.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

Bis(4,6-di-tert-butyl-2-{N-[4-(diethylamino)phenyl]carboximidoyl}phenolato)cobalt(II) top
Crystal data top
[Co(C25H35N2O)2]Z = 2
Mr = 818.03F(000) = 882
Triclinic, P1Dx = 1.075 Mg m3
a = 11.9460 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.2180 (2) ÅCell parameters from 8860 reflections
c = 17.4340 (2) Åθ = 2.2–22.1°
α = 109.348 (1)°µ = 0.38 mm1
β = 96.350 (1)°T = 295 K
γ = 98.881 (2)°Block, colourless
V = 2527.33 (6) Å30.28 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5894 reflections with I > 2σ(I)
ω and φ scanRint = 0.045
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
θmax = 24.3°, θmin = 2.0°
Tmin = 0.851, Tmax = 0.928h = 1313
38553 measured reflectionsk = 1515
8091 independent reflectionsl = 2020
Refinement top
Refinement on F2105 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.146 w = 1/[σ2(Fo2) + (0.0808P)2 + 0.0839P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
8091 reflectionsΔρmax = 0.43 e Å3
592 parametersΔρmin = 0.36 e Å3
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 H atoms were positioned geometrically and refined as riding, with C–H = 0.93–0.97 Å, and Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for methyl H atoms. A rotating model was used for the methyl groups.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.7275 (2)0.1630 (2)0.29792 (15)0.0416 (6)
C20.6716 (2)0.2748 (2)0.25854 (16)0.0491 (7)
C30.6434 (2)0.3331 (2)0.30879 (18)0.0555 (7)
H30.6067820.4061700.2830270.067*
C40.6648 (2)0.2921 (2)0.39406 (18)0.0521 (7)
C50.7202 (2)0.1854 (2)0.43080 (17)0.0487 (7)
H50.7370780.1553960.4881240.058*
C60.7527 (2)0.1189 (2)0.38531 (15)0.0409 (6)
C70.6438 (3)0.3258 (2)0.16368 (18)0.0656 (8)
C80.7551 (3)0.3166 (3)0.1273 (2)0.0901 (11)
H8A0.7373750.3516940.0683970.135*
H8B0.8079890.3515620.1497750.135*
H8C0.7892870.2407340.1411750.135*
C90.5597 (3)0.2679 (3)0.1303 (2)0.0868 (11)
H9A0.4890360.2777170.1508770.130*
H9B0.5445910.2983770.0711070.130*
H9C0.5926240.1911080.1480600.130*
C100.5880 (4)0.4482 (3)0.1350 (2)0.1087 (15)
H10A0.5161800.4563720.1543790.163*
H10B0.6384700.4856520.1570710.163*
H10C0.5746980.4790190.0758460.163*
C110.6289 (3)0.3656 (2)0.44291 (19)0.0719 (7)
C120.5005 (4)0.4117 (4)0.4184 (3)0.0872 (9)0.802 (3)
H12A0.4780520.4578830.4488390.131*0.802 (3)
H12B0.4824100.4537150.3603740.131*0.802 (3)
H12C0.4597480.3526220.4305570.131*0.802 (3)
C130.6935 (4)0.4590 (3)0.4250 (3)0.0826 (9)0.802 (3)
H13A0.7747180.4297580.4405930.124*0.802 (3)
H13B0.6756740.5020090.3671350.124*0.802 (3)
H13C0.6708120.5043720.4560290.124*0.802 (3)
C140.6576 (4)0.3049 (3)0.5350 (2)0.0847 (9)0.802 (3)
H14A0.6305500.3529600.5629690.127*0.802 (3)
H14B0.6210430.2429770.5493030.127*0.802 (3)
H14C0.7394090.2801720.5514070.127*0.802 (3)
C12A0.5553 (16)0.3073 (13)0.5019 (11)0.0844 (11)0.198 (3)
H12D0.4780140.3212980.4731540.127*0.198 (3)
H12E0.5862330.2298930.5228120.127*0.198 (3)
H12F0.5552890.3337440.5469200.127*0.198 (3)
C13A0.7398 (10)0.3798 (15)0.4855 (11)0.0827 (11)0.198 (3)
H13D0.7989410.3163600.4961540.124*0.198 (3)
H13E0.7626640.4435090.4506150.124*0.198 (3)
H13F0.7281530.3886020.5367220.124*0.198 (3)
C14A0.5353 (15)0.4650 (12)0.3886 (10)0.0848 (13)0.198 (3)
H14D0.5702440.5189500.3532170.127*0.198 (3)
H14E0.4818060.4422590.3556560.127*0.198 (3)
H14F0.4953800.4958570.4231320.127*0.198 (3)
C150.8064 (2)0.0076 (2)0.43271 (15)0.0423 (6)
H150.8205290.0100260.4896240.051*
C160.8867 (2)0.1774 (2)0.46795 (16)0.0456 (6)
C170.9717 (2)0.1937 (2)0.53267 (17)0.0516 (7)
H171.0023260.1347010.5364980.062*
C181.0128 (2)0.2958 (2)0.59233 (18)0.0614 (8)
H181.0705370.3038510.6356090.074*
C190.9708 (3)0.3870 (2)0.5898 (2)0.0684 (9)
C200.8859 (3)0.3693 (2)0.5225 (2)0.0848 (11)
H200.8555820.4281290.5178820.102*
C210.8457 (3)0.2674 (2)0.46256 (19)0.0710 (9)
H210.7901970.2590230.4178720.085*
C221.0854 (4)0.5023 (3)0.7256 (3)0.1123 (13)
H22A1.1205680.5791680.7535730.135*
H22B1.1467050.4623980.7128870.135*
C231.0226 (5)0.4633 (5)0.7818 (3)0.146 (2)
H23A0.9561040.4956670.7893260.220*
H23B1.0718300.4836790.8341460.220*
H23C0.9987100.3849880.7584920.220*
C240.9676 (6)0.5846 (3)0.6445 (3)0.1307 (19)
H24A0.9527870.5790070.5872560.157*
H24B1.0259360.6502190.6741670.157*
C250.8610 (6)0.5962 (4)0.6791 (4)0.163 (3)
H25A0.8033230.5308390.6512090.244*
H25B0.8339880.6577010.6717640.244*
H25C0.8762780.6076720.7369380.244*
C260.7745 (3)0.1623 (2)0.18080 (17)0.0545 (7)
C270.6898 (3)0.1961 (2)0.13590 (18)0.0626 (8)
C280.7208 (4)0.2304 (3)0.0733 (2)0.0753 (10)
H280.6656580.2534950.0447260.090*
C290.8283 (3)0.2333 (3)0.0495 (2)0.0760 (10)
C300.9069 (3)0.1995 (3)0.09240 (19)0.0744 (9)
H300.9798030.2008110.0782980.089*
C310.8839 (3)0.1624 (2)0.15762 (17)0.0588 (8)
C320.5673 (3)0.1897 (3)0.1547 (2)0.0740 (9)
C330.5136 (3)0.0718 (3)0.1415 (2)0.0919 (11)
H33A0.5586360.0464520.1776590.138*
H33B0.5114340.0265570.0852020.138*
H33C0.4366990.0680860.1531900.138*
C340.5693 (4)0.2634 (3)0.2430 (3)0.1117 (14)
H34A0.6141500.2394390.2803180.168*
H34B0.4921380.2596080.2541160.168*
H34C0.6028800.3374880.2503530.168*
C350.4890 (4)0.2265 (4)0.0968 (3)0.1154 (15)
H35A0.4133230.2219690.1108670.173*
H35B0.4845270.1796990.0406640.173*
H35C0.5202940.3007290.1030260.173*
C360.8494 (4)0.2657 (3)0.0253 (2)0.1072 (11)
C370.7516 (10)0.191 (2)0.0954 (14)0.124 (2)0.452 (9)
H37A0.7592470.2069110.1446530.185*0.452 (9)
H37B0.6788620.2031750.0799810.185*0.452 (9)
H37C0.7558260.1157100.1054850.185*0.452 (9)
C380.8413 (13)0.3803 (8)0.0184 (10)0.1228 (16)0.452 (9)
H38A0.8363020.3859190.0720990.184*0.452 (9)
H38B0.9084600.4303430.0173110.184*0.452 (9)
H38C0.7739760.3979650.0040550.184*0.452 (9)
C390.9580 (8)0.2355 (12)0.0555 (7)0.1231 (16)0.452 (9)
H39A0.9699900.2604690.1003650.185*0.452 (9)
H39B0.9503750.1574320.0741100.185*0.452 (9)
H39C1.0224130.2695040.0112780.185*0.452 (9)
C37A0.7884 (10)0.1753 (17)0.1055 (12)0.126 (2)0.548 (9)
H37D0.7907280.2023220.1502340.190*0.548 (9)
H37E0.7097290.1522830.1013690.190*0.548 (9)
H37F0.8261190.1142470.1156700.190*0.548 (9)
C38A0.7892 (11)0.3676 (8)0.0172 (8)0.1213 (18)0.548 (9)
H38D0.8015400.3930200.0617100.182*0.548 (9)
H38E0.8216450.4254410.0345000.182*0.548 (9)
H38F0.7080900.3454830.0194070.182*0.548 (9)
C39A0.9775 (8)0.3155 (10)0.0167 (7)0.1234 (15)0.548 (9)
H39D1.0217700.2595870.0219340.185*0.548 (9)
H39E1.0031850.3725520.0363150.185*0.548 (9)
H39F0.9874620.3455120.0593120.185*0.548 (9)
C400.9729 (3)0.1215 (2)0.19182 (17)0.0596 (8)
H401.0420640.1294690.1725990.072*
C411.0694 (2)0.0376 (2)0.27158 (16)0.0504 (7)
C421.0537 (2)0.0517 (2)0.29725 (18)0.0581 (7)
H420.9796200.0839460.2990530.070*
C431.1444 (2)0.0933 (3)0.31992 (18)0.0614 (8)
H431.1305100.1535330.3364360.074*
C441.2574 (2)0.0476 (3)0.31887 (17)0.0596 (8)
C451.2722 (3)0.0442 (2)0.29534 (19)0.0651 (8)
H451.3462970.0781220.2949350.078*
C461.1813 (2)0.0855 (2)0.27293 (18)0.0605 (8)
H461.1949560.1472350.2582520.073*
C471.4628 (3)0.0539 (3)0.3249 (3)0.0932 (12)
H47A1.4548600.0370220.2747780.112*
H47B1.5041180.1133250.3161980.112*
C481.5312 (3)0.0439 (4)0.3937 (3)0.139 (2)
H48A1.4872100.1004320.4067660.209*
H48B1.6009360.0699230.3773480.209*
H48C1.5497280.0245810.4413140.209*
C491.3332 (3)0.1838 (3)0.3668 (2)0.0879 (10)
H49A1.2728920.1785740.4000260.105*
H49B1.4036590.1816470.4013920.105*
C501.3027 (4)0.2902 (3)0.2973 (3)0.1095 (13)
H50A1.2335020.2927440.2623770.164*
H50B1.2906660.3486370.3185280.164*
H50C1.3640970.2980370.2660060.164*
N10.83819 (17)0.07252 (16)0.40685 (12)0.0425 (5)
N20.96972 (19)0.07446 (18)0.24633 (13)0.0509 (6)
N31.0126 (3)0.4891 (2)0.64881 (19)0.0967 (10)
N41.3492 (2)0.0897 (2)0.34047 (19)0.0805 (8)
O10.74859 (17)0.13208 (15)0.24188 (12)0.0600 (5)
O20.75399 (15)0.10400 (14)0.25273 (11)0.0515 (5)
CO10.82532 (3)0.04522 (3)0.28727 (2)0.04779 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0400 (14)0.0473 (15)0.0432 (15)0.0107 (12)0.0066 (12)0.0226 (13)
C20.0516 (16)0.0493 (16)0.0465 (16)0.0101 (13)0.0042 (13)0.0185 (14)
C30.0653 (18)0.0441 (16)0.0550 (19)0.0027 (13)0.0051 (14)0.0203 (14)
C40.0565 (17)0.0516 (17)0.0545 (18)0.0089 (13)0.0108 (14)0.0274 (15)
C50.0573 (17)0.0499 (16)0.0425 (15)0.0098 (13)0.0081 (13)0.0218 (13)
C60.0424 (14)0.0446 (15)0.0404 (15)0.0102 (11)0.0058 (11)0.0211 (13)
C70.089 (2)0.0531 (18)0.0467 (18)0.0040 (16)0.0022 (16)0.0155 (15)
C80.118 (3)0.091 (3)0.062 (2)0.030 (2)0.034 (2)0.019 (2)
C90.092 (3)0.101 (3)0.056 (2)0.008 (2)0.0154 (18)0.027 (2)
C100.168 (4)0.069 (2)0.055 (2)0.019 (2)0.003 (2)0.0048 (19)
C110.0978 (17)0.0614 (16)0.0729 (15)0.0074 (12)0.0216 (14)0.0469 (14)
C120.0994 (17)0.083 (2)0.0907 (19)0.0038 (14)0.0222 (16)0.0503 (17)
C130.110 (2)0.0690 (17)0.0847 (19)0.0148 (14)0.0173 (17)0.0495 (15)
C140.114 (2)0.0785 (19)0.0745 (15)0.0078 (16)0.0229 (15)0.0478 (14)
C12A0.105 (2)0.080 (2)0.081 (2)0.0084 (17)0.0287 (17)0.0464 (19)
C13A0.110 (2)0.074 (2)0.080 (2)0.0142 (17)0.0164 (17)0.0509 (18)
C14A0.103 (2)0.074 (2)0.087 (2)0.0041 (17)0.0185 (19)0.0468 (19)
C150.0431 (14)0.0513 (16)0.0349 (14)0.0113 (12)0.0057 (11)0.0178 (13)
C160.0507 (16)0.0426 (15)0.0435 (15)0.0036 (12)0.0074 (13)0.0179 (13)
C170.0483 (16)0.0502 (17)0.0545 (18)0.0098 (13)0.0043 (14)0.0179 (15)
C180.0570 (18)0.065 (2)0.0527 (18)0.0050 (15)0.0037 (14)0.0162 (16)
C190.086 (2)0.0522 (19)0.059 (2)0.0042 (16)0.0000 (18)0.0173 (16)
C200.131 (3)0.0429 (18)0.074 (2)0.0189 (19)0.011 (2)0.0210 (18)
C210.097 (2)0.0518 (19)0.0578 (19)0.0114 (17)0.0149 (17)0.0221 (16)
C220.118 (3)0.082 (3)0.094 (2)0.016 (2)0.0260 (19)0.009 (2)
C230.174 (5)0.185 (5)0.077 (3)0.078 (4)0.004 (3)0.030 (3)
C240.204 (6)0.058 (3)0.098 (4)0.003 (3)0.020 (4)0.012 (2)
C250.217 (7)0.110 (4)0.158 (6)0.076 (4)0.004 (5)0.035 (4)
C260.081 (2)0.0424 (15)0.0418 (16)0.0072 (14)0.0040 (15)0.0211 (13)
C270.093 (2)0.0466 (17)0.0488 (17)0.0129 (15)0.0014 (16)0.0223 (15)
C280.111 (3)0.061 (2)0.056 (2)0.0119 (19)0.006 (2)0.0320 (17)
C290.108 (3)0.073 (2)0.0515 (19)0.005 (2)0.0001 (19)0.0381 (18)
C300.088 (2)0.084 (2)0.060 (2)0.0049 (19)0.0132 (18)0.0426 (19)
C310.075 (2)0.0591 (18)0.0475 (17)0.0064 (15)0.0057 (15)0.0300 (15)
C320.090 (3)0.068 (2)0.075 (2)0.0286 (18)0.0062 (19)0.0353 (19)
C330.091 (3)0.093 (3)0.099 (3)0.010 (2)0.011 (2)0.048 (2)
C340.133 (4)0.106 (3)0.103 (3)0.059 (3)0.025 (3)0.029 (3)
C350.112 (3)0.127 (4)0.133 (4)0.040 (3)0.003 (3)0.081 (3)
C360.162 (3)0.114 (2)0.0623 (18)0.015 (2)0.019 (2)0.0590 (18)
C370.178 (4)0.143 (5)0.050 (5)0.035 (6)0.019 (6)0.035 (3)
C380.172 (4)0.124 (3)0.109 (3)0.014 (3)0.042 (3)0.090 (3)
C390.170 (3)0.132 (3)0.104 (4)0.017 (3)0.046 (3)0.089 (3)
C37A0.184 (5)0.145 (5)0.054 (4)0.038 (6)0.025 (6)0.037 (2)
C38A0.171 (4)0.122 (3)0.109 (3)0.014 (3)0.041 (4)0.091 (3)
C39A0.170 (3)0.129 (3)0.107 (3)0.015 (3)0.043 (3)0.089 (3)
C400.0631 (19)0.0670 (19)0.0467 (17)0.0008 (15)0.0099 (14)0.0230 (16)
C410.0524 (17)0.0573 (17)0.0428 (15)0.0101 (14)0.0112 (13)0.0192 (14)
C420.0491 (17)0.076 (2)0.0617 (19)0.0145 (15)0.0160 (14)0.0374 (17)
C430.0580 (19)0.078 (2)0.0628 (19)0.0206 (16)0.0171 (15)0.0385 (17)
C440.0548 (19)0.078 (2)0.0507 (18)0.0221 (16)0.0126 (14)0.0236 (16)
C450.0477 (17)0.071 (2)0.072 (2)0.0048 (15)0.0116 (15)0.0218 (18)
C460.0601 (19)0.0571 (18)0.064 (2)0.0071 (15)0.0168 (15)0.0215 (16)
C470.0572 (18)0.106 (3)0.118 (3)0.030 (2)0.022 (2)0.033 (3)
C480.072 (3)0.125 (4)0.185 (5)0.026 (3)0.010 (3)0.016 (4)
C490.076 (2)0.120 (3)0.088 (2)0.043 (2)0.014 (2)0.0536 (19)
C500.109 (3)0.103 (3)0.127 (3)0.033 (3)0.019 (3)0.050 (2)
N10.0425 (12)0.0460 (12)0.0436 (12)0.0081 (10)0.0058 (10)0.0227 (11)
N20.0563 (14)0.0540 (14)0.0453 (13)0.0077 (11)0.0082 (11)0.0232 (12)
N30.127 (3)0.0534 (17)0.0806 (19)0.0029 (17)0.0119 (16)0.0025 (16)
N40.0546 (14)0.095 (2)0.098 (2)0.0249 (14)0.0105 (14)0.0391 (18)
O10.0760 (13)0.0679 (13)0.0530 (12)0.0266 (10)0.0176 (10)0.0362 (10)
O20.0610 (11)0.0532 (11)0.0426 (10)0.0054 (9)0.0069 (9)0.0236 (9)
CO10.0559 (3)0.0516 (3)0.0434 (2)0.01044 (17)0.00958 (17)0.02650 (19)
Geometric parameters (Å, º) top
C1—O21.309 (3)C26—C271.426 (4)
C1—C61.417 (3)C27—C281.379 (4)
C1—C21.422 (3)C27—C321.530 (5)
C2—C31.381 (4)C28—C291.391 (5)
C2—C71.540 (4)C28—H280.9300
C3—C41.381 (4)C29—C301.355 (4)
C3—H30.9300C29—C361.535 (5)
C4—C51.362 (4)C30—C311.417 (4)
C4—C111.534 (4)C30—H300.9300
C5—C61.406 (3)C31—C401.424 (4)
C5—H50.9300C32—C341.520 (5)
C6—C151.430 (3)C32—C331.522 (4)
C7—C91.529 (4)C32—C351.545 (5)
C7—C101.540 (4)C33—H33A0.9600
C7—C81.540 (5)C33—H33B0.9600
C8—H8A0.9600C33—H33C0.9600
C8—H8B0.9600C34—H34A0.9600
C8—H8C0.9600C34—H34B0.9600
C9—H9A0.9600C34—H34C0.9600
C9—H9B0.9600C35—H35A0.9600
C9—H9C0.9600C35—H35B0.9600
C10—H10A0.9600C35—H35C0.9600
C10—H10B0.9600C36—C381.498 (7)
C10—H10C0.9600C36—C391.514 (6)
C11—C141.510 (4)C36—C37A1.522 (12)
C11—C13A1.515 (8)C36—C371.538 (8)
C11—C121.517 (4)C36—C39A1.540 (10)
C11—C12A1.518 (8)C36—C38A1.595 (11)
C11—C131.521 (4)C37—H37A0.9600
C11—C14A1.536 (8)C37—H37B0.9600
C12—H12A0.9600C37—H37C0.9600
C12—H12B0.9600C38—H38A0.9600
C12—H12C0.9600C38—H38B0.9600
C13—H13A0.9600C38—H38C0.9600
C13—H13B0.9600C39—H39A0.9600
C13—H13C0.9600C39—H39B0.9600
C14—H14A0.9600C39—H39C0.9600
C14—H14B0.9600C37A—H37D0.9600
C14—H14C0.9600C37A—H37E0.9600
C12A—H12D0.9600C37A—H37F0.9600
C12A—H12E0.9600C38A—H38D0.9600
C12A—H12F0.9600C38A—H38E0.9600
C13A—H13D0.9600C38A—H38F0.9600
C13A—H13E0.9600C39A—H39D0.9600
C13A—H13F0.9600C39A—H39E0.9600
C14A—H14D0.9600C39A—H39F0.9600
C14A—H14E0.9600C40—N21.297 (3)
C14A—H14F0.9600C40—H400.9300
C15—N11.303 (3)C41—C461.383 (4)
C15—H150.9300C41—C421.388 (4)
C16—C171.367 (4)C41—N21.434 (3)
C16—C211.381 (4)C42—C431.366 (4)
C16—N11.425 (3)C42—H420.9300
C17—C181.377 (4)C43—C441.396 (4)
C17—H170.9300C43—H430.9300
C18—C191.387 (4)C44—N41.374 (4)
C18—H180.9300C44—C451.397 (4)
C19—N31.374 (4)C45—C461.364 (4)
C19—C201.394 (4)C45—H450.9300
C20—C211.375 (4)C46—H460.9300
C20—H200.9300C47—N41.452 (4)
C21—H210.9300C47—C481.485 (5)
C22—N31.457 (5)C47—H47A0.9700
C22—C231.472 (7)C47—H47B0.9700
C22—H22A0.9700C48—H48A0.9600
C22—H22B0.9700C48—H48B0.9600
C23—H23A0.9600C48—H48C0.9600
C23—H23B0.9600C49—N41.456 (4)
C23—H23C0.9600C49—C501.480 (5)
C24—N31.467 (5)C49—H49A0.9700
C24—C251.476 (7)C49—H49B0.9700
C24—H24A0.9700C50—H50A0.9600
C24—H24B0.9700C50—H50B0.9600
C25—H25A0.9600C50—H50C0.9600
C25—H25B0.9600N1—CO11.978 (2)
C25—H25C0.9600N2—CO11.971 (2)
C26—O11.306 (3)O1—CO11.8844 (18)
C26—C311.409 (4)O2—CO11.8867 (17)
O2—C1—C6122.0 (2)C30—C29—C36123.9 (4)
O2—C1—C2119.3 (2)C28—C29—C36119.9 (3)
C6—C1—C2118.6 (2)C29—C30—C31123.4 (3)
C3—C2—C1117.2 (2)C29—C30—H30118.3
C3—C2—C7122.7 (2)C31—C30—H30118.3
C1—C2—C7120.1 (2)C26—C31—C30118.9 (3)
C2—C3—C4125.6 (3)C26—C31—C40124.8 (2)
C2—C3—H3117.2C30—C31—C40116.3 (3)
C4—C3—H3117.2C34—C32—C33110.3 (3)
C5—C4—C3116.5 (2)C34—C32—C27109.9 (3)
C5—C4—C11123.0 (3)C33—C32—C27109.7 (3)
C3—C4—C11120.5 (3)C34—C32—C35108.0 (3)
C4—C5—C6122.5 (2)C33—C32—C35106.8 (3)
C4—C5—H5118.8C27—C32—C35112.0 (3)
C6—C5—H5118.8C32—C33—H33A109.5
C5—C6—C1119.6 (2)C32—C33—H33B109.5
C5—C6—C15115.9 (2)H33A—C33—H33B109.5
C1—C6—C15124.4 (2)C32—C33—H33C109.5
C9—C7—C2109.8 (2)H33A—C33—H33C109.5
C9—C7—C10108.2 (3)H33B—C33—H33C109.5
C2—C7—C10110.9 (2)C32—C34—H34A109.5
C9—C7—C8110.2 (3)C32—C34—H34B109.5
C2—C7—C8110.1 (3)H34A—C34—H34B109.5
C10—C7—C8107.6 (3)C32—C34—H34C109.5
C7—C8—H8A109.5H34A—C34—H34C109.5
C7—C8—H8B109.5H34B—C34—H34C109.5
H8A—C8—H8B109.5C32—C35—H35A109.5
C7—C8—H8C109.5C32—C35—H35B109.5
H8A—C8—H8C109.5H35A—C35—H35B109.5
H8B—C8—H8C109.5C32—C35—H35C109.5
C7—C9—H9A109.5H35A—C35—H35C109.5
C7—C9—H9B109.5H35B—C35—H35C109.5
H9A—C9—H9B109.5C38—C36—C39111.9 (7)
C7—C9—H9C109.5C38—C36—C29116.8 (6)
H9A—C9—H9C109.5C39—C36—C29112.2 (5)
H9B—C9—H9C109.5C37A—C36—C29111.0 (12)
C7—C10—H10A109.5C38—C36—C37105.6 (14)
C7—C10—H10B109.5C39—C36—C37104.3 (6)
H10A—C10—H10B109.5C29—C36—C37104.8 (14)
C7—C10—H10C109.5C37A—C36—C39A119.1 (8)
H10A—C10—H10C109.5C29—C36—C39A110.5 (4)
H10B—C10—H10C109.5C37A—C36—C38A106.4 (10)
C14—C11—C12109.2 (3)C29—C36—C38A105.7 (5)
C13A—C11—C12A113.9 (11)C39A—C36—C38A102.9 (6)
C14—C11—C13106.2 (3)C36—C37—H37A109.5
C12—C11—C13109.5 (3)C36—C37—H37B109.5
C14—C11—C4112.3 (3)H37A—C37—H37B109.5
C13A—C11—C4105.9 (6)C36—C37—H37C109.5
C12—C11—C4109.5 (3)H37A—C37—H37C109.5
C12A—C11—C4106.7 (7)H37B—C37—H37C109.5
C13—C11—C4110.0 (3)C36—C38—H38A109.5
C13A—C11—C14A121.2 (10)C36—C38—H38B109.5
C12A—C11—C14A98.0 (11)H38A—C38—H38B109.5
C4—C11—C14A110.4 (7)C36—C38—H38C109.5
C11—C12—H12A109.5H38A—C38—H38C109.5
C11—C12—H12B109.5H38B—C38—H38C109.5
H12A—C12—H12B109.5C36—C39—H39A109.5
C11—C12—H12C109.5C36—C39—H39B109.5
H12A—C12—H12C109.5H39A—C39—H39B109.5
H12B—C12—H12C109.5C36—C39—H39C109.5
C11—C13—H13A109.5H39A—C39—H39C109.5
C11—C13—H13B109.5H39B—C39—H39C109.5
H13A—C13—H13B109.5C36—C37A—H37D109.5
C11—C13—H13C109.5C36—C37A—H37E109.5
H13A—C13—H13C109.5H37D—C37A—H37E109.5
H13B—C13—H13C109.5C36—C37A—H37F109.5
C11—C14—H14A109.5H37D—C37A—H37F109.5
C11—C14—H14B109.5H37E—C37A—H37F109.5
H14A—C14—H14B109.5C36—C38A—H38D109.5
C11—C14—H14C109.5C36—C38A—H38E109.5
H14A—C14—H14C109.5H38D—C38A—H38E109.5
H14B—C14—H14C109.5C36—C38A—H38F109.5
C11—C12A—H12D109.5H38D—C38A—H38F109.5
C11—C12A—H12E109.5H38E—C38A—H38F109.5
H12D—C12A—H12E109.5C36—C39A—H39D109.5
C11—C12A—H12F109.5C36—C39A—H39E109.5
H12D—C12A—H12F109.5H39D—C39A—H39E109.5
H12E—C12A—H12F109.5C36—C39A—H39F109.5
C11—C13A—H13D109.5H39D—C39A—H39F109.5
C11—C13A—H13E109.5H39E—C39A—H39F109.5
H13D—C13A—H13E109.5N2—C40—C31128.3 (3)
C11—C13A—H13F109.5N2—C40—H40115.8
H13D—C13A—H13F109.5C31—C40—H40115.8
H13E—C13A—H13F109.5C46—C41—C42117.2 (3)
C11—C14A—H14D109.5C46—C41—N2124.4 (2)
C11—C14A—H14E109.5C42—C41—N2118.4 (2)
H14D—C14A—H14E109.5C43—C42—C41121.7 (3)
C11—C14A—H14F109.5C43—C42—H42119.2
H14D—C14A—H14F109.5C41—C42—H42119.2
H14E—C14A—H14F109.5C42—C43—C44121.5 (3)
N1—C15—C6128.7 (2)C42—C43—H43119.2
N1—C15—H15115.7C44—C43—H43119.2
C6—C15—H15115.7N4—C44—C43122.1 (3)
C17—C16—C21117.9 (3)N4—C44—C45121.7 (3)
C17—C16—N1123.2 (2)C43—C44—C45116.2 (3)
C21—C16—N1118.9 (2)C46—C45—C44121.9 (3)
C16—C17—C18121.3 (3)C46—C45—H45119.0
C16—C17—H17119.3C44—C45—H45119.0
C18—C17—H17119.3C45—C46—C41121.4 (3)
C17—C18—C19122.0 (3)C45—C46—H46119.3
C17—C18—H18119.0C41—C46—H46119.3
C19—C18—H18119.0N4—C47—C48112.9 (3)
N3—C19—C18122.1 (3)N4—C47—H47A109.0
N3—C19—C20122.0 (3)C48—C47—H47A109.0
C18—C19—C20115.9 (3)N4—C47—H47B109.0
C21—C20—C19122.0 (3)C48—C47—H47B109.0
C21—C20—H20119.0H47A—C47—H47B107.8
C19—C20—H20119.0C47—C48—H48A109.5
C20—C21—C16120.8 (3)C47—C48—H48B109.5
C20—C21—H21119.6H48A—C48—H48B109.5
C16—C21—H21119.6C47—C48—H48C109.5
N3—C22—C23113.3 (4)H48A—C48—H48C109.5
N3—C22—H22A108.9H48B—C48—H48C109.5
C23—C22—H22A108.9N4—C49—C50113.5 (3)
N3—C22—H22B108.9N4—C49—H49A108.9
C23—C22—H22B108.9C50—C49—H49A108.9
H22A—C22—H22B107.7N4—C49—H49B108.9
C22—C23—H23A109.5C50—C49—H49B108.9
C22—C23—H23B109.5H49A—C49—H49B107.7
H23A—C23—H23B109.5C49—C50—H50A109.5
C22—C23—H23C109.5C49—C50—H50B109.5
H23A—C23—H23C109.5H50A—C50—H50B109.5
H23B—C23—H23C109.5C49—C50—H50C109.5
N3—C24—C25113.7 (4)H50A—C50—H50C109.5
N3—C24—H24A108.8H50B—C50—H50C109.5
C25—C24—H24A108.8C15—N1—C16117.2 (2)
N3—C24—H24B108.8C15—N1—CO1120.36 (17)
C25—C24—H24B108.8C16—N1—CO1122.34 (15)
H24A—C24—H24B107.7C40—N2—C41119.3 (2)
C24—C25—H25A109.5C40—N2—CO1119.7 (2)
C24—C25—H25B109.5C41—N2—CO1120.85 (16)
H25A—C25—H25B109.5C19—N3—C22120.7 (3)
C24—C25—H25C109.5C19—N3—C24121.2 (3)
H25A—C25—H25C109.5C22—N3—C24117.1 (3)
H25B—C25—H25C109.5C44—N4—C47121.0 (3)
O1—C26—C31122.1 (3)C44—N4—C49121.4 (3)
O1—C26—C27119.2 (3)C47—N4—C49116.9 (3)
C31—C26—C27118.8 (3)C26—O1—CO1126.01 (19)
C28—C27—C26117.8 (3)C1—O2—CO1128.76 (16)
C28—C27—C32121.4 (3)O1—CO1—O2116.00 (8)
C26—C27—C32120.7 (3)O1—CO1—N295.76 (8)
C27—C28—C29125.1 (3)O2—CO1—N2114.94 (8)
C27—C28—H28117.5O1—CO1—N1119.33 (8)
C29—C28—H28117.5O2—CO1—N195.57 (8)
C30—C29—C28116.1 (3)N2—CO1—N1116.77 (9)
O2—C1—C2—C3178.8 (2)C26—C27—C32—C3359.5 (4)
C6—C1—C2—C31.1 (4)C28—C27—C32—C350.5 (4)
O2—C1—C2—C70.7 (4)C26—C27—C32—C35178.0 (3)
C6—C1—C2—C7179.4 (2)C30—C29—C36—C38120.1 (8)
C1—C2—C3—C40.0 (4)C28—C29—C36—C3864.3 (9)
C7—C2—C3—C4179.4 (3)C30—C29—C36—C3910.9 (8)
C2—C3—C4—C51.1 (4)C28—C29—C36—C39164.7 (7)
C2—C3—C4—C11179.9 (3)C30—C29—C36—C37A103.3 (7)
C3—C4—C5—C61.0 (4)C28—C29—C36—C37A72.3 (8)
C11—C4—C5—C6180.0 (3)C30—C29—C36—C37123.5 (8)
C4—C5—C6—C10.2 (4)C28—C29—C36—C3752.2 (9)
C4—C5—C6—C15177.8 (2)C30—C29—C36—C39A31.2 (7)
O2—C1—C6—C5178.7 (2)C28—C29—C36—C39A153.2 (6)
C2—C1—C6—C51.2 (3)C30—C29—C36—C38A141.8 (6)
O2—C1—C6—C151.2 (4)C28—C29—C36—C38A42.6 (6)
C2—C1—C6—C15178.7 (2)C26—C31—C40—N22.7 (5)
C3—C2—C7—C9116.6 (3)C30—C31—C40—N2173.5 (3)
C1—C2—C7—C962.8 (3)C46—C41—C42—C432.5 (4)
C3—C2—C7—C102.9 (4)N2—C41—C42—C43178.1 (3)
C1—C2—C7—C10177.7 (3)C41—C42—C43—C440.4 (5)
C3—C2—C7—C8121.9 (3)C42—C43—C44—N4179.1 (3)
C1—C2—C7—C858.7 (3)C42—C43—C44—C451.5 (4)
C5—C4—C11—C142.3 (4)N4—C44—C45—C46179.2 (3)
C3—C4—C11—C14178.8 (3)C43—C44—C45—C461.4 (4)
C5—C4—C11—C13A66.3 (9)C44—C45—C46—C410.7 (5)
C3—C4—C11—C13A112.7 (8)C42—C41—C46—C452.6 (4)
C5—C4—C11—C12123.7 (3)N2—C41—C46—C45178.0 (3)
C3—C4—C11—C1257.3 (4)C6—C15—N1—C16177.9 (2)
C5—C4—C11—C12A55.4 (9)C6—C15—N1—CO14.9 (3)
C3—C4—C11—C12A125.6 (9)C17—C16—N1—C1548.4 (3)
C5—C4—C11—C13115.8 (3)C21—C16—N1—C15130.9 (3)
C3—C4—C11—C1363.1 (4)C17—C16—N1—CO1128.7 (2)
C5—C4—C11—C14A160.8 (10)C21—C16—N1—CO152.0 (3)
C3—C4—C11—C14A20.2 (10)C31—C40—N2—C41179.0 (3)
C5—C6—C15—N1175.3 (2)C31—C40—N2—CO13.4 (4)
C1—C6—C15—N12.2 (4)C46—C41—N2—C4029.8 (4)
C21—C16—C17—C182.1 (4)C42—C41—N2—C40150.9 (3)
N1—C16—C17—C18177.2 (2)C46—C41—N2—CO1154.7 (2)
C16—C17—C18—C190.2 (5)C42—C41—N2—CO124.7 (3)
C17—C18—C19—N3179.3 (3)C18—C19—N3—C2213.0 (6)
C17—C18—C19—C201.1 (5)C20—C19—N3—C22168.9 (4)
N3—C19—C20—C21178.7 (4)C18—C19—N3—C24179.4 (4)
C18—C19—C20—C210.5 (5)C20—C19—N3—C241.3 (6)
C19—C20—C21—C161.4 (6)C23—C22—N3—C1971.5 (5)
C17—C16—C21—C202.7 (5)C23—C22—N3—C2496.5 (5)
N1—C16—C21—C20176.7 (3)C25—C24—N3—C1983.3 (5)
O1—C26—C27—C28178.2 (3)C25—C24—N3—C2284.7 (5)
C31—C26—C27—C281.9 (4)C43—C44—N4—C47168.8 (3)
O1—C26—C27—C324.3 (4)C45—C44—N4—C4711.8 (5)
C31—C26—C27—C32175.7 (3)C43—C44—N4—C490.8 (5)
C26—C27—C28—C291.0 (5)C45—C44—N4—C49178.5 (3)
C32—C27—C28—C29176.5 (3)C48—C47—N4—C4488.3 (4)
C27—C28—C29—C300.2 (5)C48—C47—N4—C49101.6 (4)
C27—C28—C29—C36175.8 (3)C50—C49—N4—C4483.7 (4)
C28—C29—C30—C310.4 (5)C50—C49—N4—C4786.4 (4)
C36—C29—C30—C31175.4 (3)C31—C26—O1—CO120.2 (4)
O1—C26—C31—C30178.0 (3)C27—C26—O1—CO1159.71 (19)
C27—C26—C31—C302.1 (4)C6—C1—O2—CO11.0 (3)
O1—C26—C31—C405.9 (4)C2—C1—O2—CO1178.88 (16)
C27—C26—C31—C40174.0 (3)C26—O1—CO1—O2100.4 (2)
C29—C30—C31—C261.4 (5)C26—O1—CO1—N221.0 (2)
C29—C30—C31—C40175.1 (3)C26—O1—CO1—N1146.1 (2)
C28—C27—C32—C34120.6 (3)C1—O2—CO1—O1127.7 (2)
C26—C27—C32—C3462.0 (4)C1—O2—CO1—N2121.8 (2)
C28—C27—C32—C33117.9 (3)C1—O2—CO1—N11.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8C···O20.962.312.936 (4)123
C9—H9C···O20.962.352.987 (4)123
C33—H33A···O10.962.342.980 (4)123
C34—H34A···O10.962.312.955 (4)124
 

Acknowledgements

The authors acknowledge the SAIF, IIT, Madras, for the data collection.

References

First citationAdam, K. R., Anderson, P. A., Astley, T., Atkinson, I. M., Charnock, J. M., Garner, C. D., Gulbis, J. M., Hambley, T. W., Hitchman, M. A., Keene, F. R. & Tiekink, E. R. T. (1997). J. Chem. Soc. Dalton Trans. pp. 519–530.  CSD CrossRef Web of Science Google Scholar
First citationBruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, Y. M., Gao, Q., Chen, W. Q., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2015). Chem. Asian J. 10, 411–421.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationChen, Y. M., Gao, Q., Zhang, H. F., Gao, D. D., Li, Y. H., Liu, W. & Li, W. (2014). Polyhedron, 71, 91–98.  Web of Science CSD CrossRef CAS Google Scholar
First citationNair, B., Shah, A., Baluja, S. & Chanda, S. (2006). J. Serb. Chem. Soc. 71, 733–744.  Web of Science CrossRef CAS 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. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2015). Acta Cryst. C71, 9–18.  Web of Science CrossRef IUCr Journals 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
Follow IUCr Journals
Sign up for e-alerts
Follow IUCr on Twitter
Follow us on facebook
Sign up for RSS feeds