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

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ISSN: 2414-3146

Bis{3,5-di-tert-butyl-N-[(4-di­methylamino)phenyl]salicylaldiminato}cobalt(II)

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 28 March 2017; accepted 6 April 2017; online 11 April 2017)

In the title complex [systematic name: bis(2,4-di-tert-butyl-6-{N-[4-(dimethyl­amino)phenyl]carboximidoyl}phenolato)cobalt(II)], [Co(C23H31N2O)2], the cobalt(II) atom is coordinated by pairs of O and N atoms in a distorted tetra­hedral coordination geometry. The dihedral angles formed by the aromatic rings of the same ligand are 51.99 (11) and 36.58 (9)°. The mol­ecular conformation features weak intra­molecular C—H⋯O hydrogen bonds. In the crystal, inversion-related pairs of complex mol­ecules are linked into dimers by weak C—H⋯π inter­actions. The methyl C atoms of tert-butyl groups have rotational disorder, with site occupancies of 0.647 (7) and 0.617 (6) for the major components and 0.353 (7) and 0.383 (6) for the minor components. One of the methyl C atoms of the di­methyl­amino groups is also disordered over two orientations, with an occupancy ratio of 0.75 (4):0.25 (4).

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

Structure description

Metal complexes of N- and O-chelating ligands have attracted considerable attention because of their inter­esting physicochemical properties and pronounced biological activities. The N and O atoms 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.]). Schiff base–cobalt(II) metal complexes are constantly used in numerous applications varying from catalysis to pharmaceuticals (Holla et al., 2003[Holla, B. S., Veerendra, B., Shivananda, M. K. & Poojary, B. (2003). Eur. J. Med. Chem. 38, 759-767.]). We herein report the synthesis and the structure of the title compound (Fig. 1[link]). The metal cation has a distorted tetra­hedral coordination geometry provided by two O and two N atoms. The Co—O distances [Co1—O1 = 1.8844 (19), Co1—O2 = 1.8882 (19), Co1—N1 = 1.980 (2), Co1—N2 = 1.984 (2) Å] agree well with the values observed 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.]).

[Figure 1]
Figure 1
The mol­ecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

The dihedral angle between the aromatic rings C1–C6 and C24–C29 is 85.85 (15)° while the C16–C21 ring makes a dihedral angle of 55.59 (17)° with the C39–C44 ring. The mol­ecular conformation is stabilized by weak C—H⋯O hydrogen bonds (Table 1[link]). The crystal structure exhibits dimeric units formed by weak C—H⋯π inter­actions (Table 1[link]) occurring between inversion-related complex mol­ecules..

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C8—H8C⋯O1 0.96 2.38 3.007 (4) 123
C9—H9A⋯O1 0.96 2.28 2.953 (4) 126
C32—H32C⋯O2 0.96 2.33 2.974 (4) 124
C33—H33C⋯O2 0.96 2.28 2.925 (4) 124
C45—H45BCgi 0.96 2.96 3.914 (5) 171
Symmetry code: (i) -x, -y, -z.

Synthesis and crystallization

Methano­lic solutions of the Schiff base (1 mmol, 10 ml) and Co(AcO)2·H2O (0.5 mmol; 10 ml) were mixed thoroughly and boiled under reflux for 4–6 h, and then cooled to room temperature. The resulting precipitate was filtered, washed in ice-cold ethanol and dried in vacuo. X-ray quality single crystals were grown by layering a CHCl3 (3 ml) solution 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 exhibit rotational disorder, with site occupancies of 0.647 (7) (C12–C14) and 0.617 (6) (C36–C38) for the major components. One methyl C atom of the di­methyl­amino groups is disordered over two orientations with site occupancies of 0.75 (4) and 0.25 (4) for the major (C46A) and minor (C46) components, respectively. The anisotropic displacement parameters of the disordered C atoms were restrained by SIMU instructions within 0.001 standard deviations. DELU restraints were also applied. The C—C and C—N bond lengths involving the disordered atoms were restrained to 1.50 (1) and 1.40 (1) Å, respectively. A potential solvent-accessible void of 179 Å3 was detected but no residual electron density could be located in the final difference-Fourier map.

Table 2
Experimental details

Crystal data
Chemical formula [Co(C23H31N2O)2]
Mr 761.92
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 295
a, b, c (Å) 11.5598 (3), 13.3787 (4), 17.3035 (5)
α, β, γ (°) 111.756 (1), 96.694 (2), 98.293 (1)
V3) 2417.01 (12)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.39
Crystal size (mm) 0.34 × 0.30 × 0.26
 
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 0.691, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections 41823, 9288, 6088
Rint 0.056
(sin θ/λ)max−1) 0.619
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.175, 1.07
No. of reflections 9288
No. of parameters 567
No. of restraints 100
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.73, −0.42
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.]), SHELXL2016/4 (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: SHELXL2016/4 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2016/4 (Sheldrick, 2015) and PLATON (Spek, 2009).

Bis(2,4-di-tert-butyl-6-{N-[4-(dimethylamino)phenyl]carboximidoyl}phenolato)cobalt(II) top
Crystal data top
[Co(C23H31N2O)2]Z = 2
Mr = 761.92F(000) = 818
Triclinic, P1Dx = 1.047 Mg m3
a = 11.5598 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 13.3787 (4) ÅCell parameters from 5165 reflections
c = 17.3035 (5) Åθ = 2.4–22.4°
α = 111.756 (1)°µ = 0.39 mm1
β = 96.694 (2)°T = 295 K
γ = 98.293 (1)°Block, colourless
V = 2417.01 (12) Å30.34 × 0.30 × 0.26 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6088 reflections with I > 2σ(I)
ω and φ scanRint = 0.056
Absorption correction: multi-scan
(SADABS; Bruker, 2004)
θmax = 26.1°, θmin = 2.0°
Tmin = 0.691, Tmax = 0.905h = 1414
41823 measured reflectionsk = 1616
9288 independent reflectionsl = 2121
Refinement top
Refinement on F2100 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.175 w = 1/[σ2(Fo2) + (0.0983P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
9288 reflectionsΔρmax = 0.73 e Å3
567 parametersΔρmin = 0.42 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.2392 (3)0.3564 (2)0.32262 (16)0.0487 (6)
C20.3243 (3)0.3202 (2)0.36672 (17)0.0521 (7)
C30.2911 (3)0.2850 (2)0.42796 (18)0.0572 (8)
H30.3468930.2598510.4554350.069*
C40.1792 (3)0.2847 (2)0.45161 (18)0.0569 (8)
C50.1001 (3)0.3215 (2)0.41019 (18)0.0588 (8)
H50.0250300.3225220.4244850.071*
C60.1260 (3)0.3586 (2)0.34614 (18)0.0545 (7)
C70.4508 (3)0.3225 (3)0.3475 (2)0.0630 (8)
C80.5119 (3)0.4395 (3)0.3655 (2)0.0771 (10)
H8A0.5910670.4400210.3537560.116*
H8B0.5154850.4852170.4238960.116*
H8C0.4676680.4671910.3301490.116*
C90.4461 (4)0.2495 (3)0.2558 (3)0.0921 (12)
H9A0.3951950.2716780.2199230.138*
H9B0.4153400.1745080.2463840.138*
H9C0.5246980.2560070.2429880.138*
C100.5286 (4)0.2817 (4)0.4031 (3)0.1014 (14)
H10A0.4931580.2077110.3936120.152*
H10B0.5348430.3283250.4616700.152*
H10C0.6064840.2836370.3888760.152*
C110.1529 (3)0.2444 (3)0.5206 (2)0.0769 (8)
C120.1685 (9)0.1236 (5)0.4929 (4)0.0885 (12)0.647 (7)
H12A0.1178680.0795980.4391160.133*0.647 (7)
H12B0.1473900.0959680.5343090.133*0.647 (7)
H12C0.2498720.1203550.4879470.133*0.647 (7)
C130.2446 (7)0.3136 (6)0.6022 (4)0.0916 (15)0.647 (7)
H13A0.3229560.3037630.5921260.137*0.647 (7)
H13B0.2271030.2903830.6465480.137*0.647 (7)
H13C0.2410230.3898100.6187420.137*0.647 (7)
C140.0284 (6)0.2520 (7)0.5411 (5)0.0919 (13)0.647 (7)
H14A0.0147240.3244140.5507980.138*0.647 (7)
H14B0.0221570.2373740.5908660.138*0.647 (7)
H14C0.0298760.1988860.4942980.138*0.647 (7)
C12A0.0924 (15)0.1241 (7)0.4790 (7)0.0908 (14)0.353 (7)
H12D0.0926680.0929990.5209500.136*0.353 (7)
H12E0.1344470.0855200.4363260.136*0.353 (7)
H12F0.0118520.1174180.4535130.136*0.353 (7)
C13A0.2612 (10)0.2610 (12)0.5856 (8)0.0911 (15)0.353 (7)
H13D0.2370210.2643230.6375440.137*0.353 (7)
H13E0.3143180.3285090.5955210.137*0.353 (7)
H13F0.3010980.2008110.5648990.137*0.353 (7)
C14A0.0690 (12)0.3134 (12)0.5702 (8)0.0904 (16)0.353 (7)
H14D0.0063260.2977300.5337960.136*0.353 (7)
H14E0.1037410.3901460.5898330.136*0.353 (7)
H14F0.0576140.2951110.6178510.136*0.353 (7)
C150.0334 (3)0.3962 (2)0.31094 (18)0.0563 (7)
H150.0370590.3903620.3314650.068*
C160.0729 (3)0.4689 (2)0.22694 (17)0.0524 (7)
C170.1871 (3)0.4126 (3)0.2210 (2)0.0637 (8)
H170.1959650.3508160.2341350.076*
C180.2850 (3)0.4452 (3)0.1967 (2)0.0727 (9)
H180.3595530.4063230.1946020.087*
C190.2774 (3)0.5363 (3)0.1743 (2)0.0705 (9)
C200.1621 (3)0.5927 (3)0.1802 (2)0.0687 (9)
H200.1526570.6546270.1673030.082*
C210.0632 (3)0.5580 (3)0.20448 (18)0.0594 (8)
H210.0118200.5954160.2058290.071*
C220.3705 (5)0.6594 (5)0.1289 (4)0.151 (2)
H22A0.3270610.7231580.1768100.226*
H22B0.4494540.6695740.1144710.226*
H22C0.3307010.6488950.0816870.226*
C230.4932 (4)0.5161 (5)0.1508 (4)0.151 (2)
H23A0.4947990.4397690.1383680.227*
H23B0.5508590.5229280.1093000.227*
H23C0.5117860.5505840.2060050.227*
C240.2719 (2)0.6722 (2)0.20125 (16)0.0455 (6)
C250.3247 (3)0.7857 (2)0.24113 (18)0.0551 (7)
C260.3539 (3)0.8404 (3)0.1900 (2)0.0693 (9)
H260.3892960.9146040.2164680.083*
C270.3342 (4)0.7929 (3)0.1020 (2)0.0741 (10)
C280.2816 (3)0.6844 (2)0.06418 (19)0.0621 (8)
H280.2665340.6505320.0053850.075*
C290.2488 (2)0.6212 (2)0.11110 (16)0.0458 (6)
C300.1986 (2)0.5076 (2)0.06280 (16)0.0463 (6)
H300.1845930.4859980.0043290.056*
C310.3491 (3)0.8427 (3)0.3376 (2)0.0731 (10)
C320.4384 (4)0.7915 (4)0.3751 (3)0.1115 (16)
H32A0.4489020.8235350.4357230.167*
H32B0.5132900.8051600.3581420.167*
H32C0.4091780.7137040.3549190.167*
C330.2319 (4)0.8322 (3)0.3708 (2)0.0974 (13)
H33A0.1772580.8654660.3470690.146*
H33B0.2475050.8686350.4313810.146*
H33C0.1978800.7558830.3545640.146*
C340.4014 (4)0.9676 (3)0.3675 (3)0.1069 (15)
H34A0.3454181.0013600.3454130.160*
H34B0.4743030.9774150.3472510.160*
H34C0.4166111.0012490.4282250.160*
C350.3697 (5)0.8590 (3)0.0497 (3)0.1238 (15)
C360.3825 (11)0.9787 (5)0.0901 (6)0.1324 (18)0.617 (6)
H36A0.4577611.0101610.1280560.199*0.617 (6)
H36B0.3194420.9958620.1211220.199*0.617 (6)
H36C0.3787561.0085370.0473850.199*0.617 (6)
C370.2571 (8)0.8347 (6)0.0220 (5)0.1301 (17)0.617 (6)
H37A0.1909610.8568600.0040030.195*0.617 (6)
H37B0.2370300.7575450.0569470.195*0.617 (6)
H37C0.2756100.8752410.0561140.195*0.617 (6)
C380.4587 (9)0.8060 (7)0.0010 (6)0.1289 (17)0.617 (6)
H38A0.4718380.8372190.0418440.193*0.617 (6)
H38B0.4282270.7283220.0298100.193*0.617 (6)
H38C0.5324360.8188110.0363440.193*0.617 (6)
C36A0.3089 (15)0.9562 (10)0.0745 (10)0.1322 (18)0.383 (6)
H36D0.3336341.0023690.0456850.198*0.383 (6)
H36E0.3301810.9974810.1345350.198*0.383 (6)
H36F0.2242150.9304190.0588810.198*0.383 (6)
C37A0.3976 (17)0.8000 (11)0.0333 (7)0.1303 (19)0.383 (6)
H37D0.4345250.8518230.0538210.195*0.383 (6)
H37E0.3256970.7564050.0720380.195*0.383 (6)
H37F0.4510320.7529840.0285680.195*0.383 (6)
C38A0.4954 (10)0.9361 (10)0.1014 (7)0.1305 (18)0.383 (6)
H38D0.5536570.8915840.1009000.196*0.383 (6)
H38E0.4883680.9770800.1588050.196*0.383 (6)
H38F0.5197150.9860660.0755690.196*0.383 (6)
C390.1211 (3)0.3227 (2)0.02700 (17)0.0513 (7)
C400.0333 (3)0.3022 (3)0.04044 (19)0.0605 (8)
H400.0028980.3604790.0456980.073*
C410.0110 (3)0.1980 (3)0.1005 (2)0.0742 (9)
H410.0712730.1869710.1451500.089*
C420.0327 (4)0.1093 (3)0.0957 (2)0.0823 (11)
C430.1216 (4)0.1305 (3)0.0271 (3)0.1016 (15)
H430.1538010.0727470.0224230.122*
C440.1630 (4)0.2342 (3)0.0339 (2)0.0834 (11)
H440.2199770.2452090.0804530.100*
C450.0965 (6)0.0143 (4)0.2300 (3)0.143 (2)
H45A0.1671460.0097840.2126920.215*
H45B0.1161220.0911180.2661790.215*
H45C0.0632600.0267900.2601420.215*
C460.063 (4)0.075 (3)0.164 (3)0.152 (6)0.25 (4)
H46A0.1365830.0502380.1777320.228*0.25 (4)
H46B0.0233070.1447060.2082110.228*0.25 (4)
H46C0.0780340.0842420.1114870.228*0.25 (4)
C46A0.010 (2)0.0919 (8)0.1400 (9)0.155 (6)0.75 (4)
H46D0.0891340.1016030.1462200.233*0.75 (4)
H46E0.0461220.1560890.1794650.233*0.75 (4)
H46F0.0005410.0810300.0833360.233*0.75 (4)
N10.0330 (2)0.43793 (18)0.25358 (14)0.0506 (6)
N20.1700 (2)0.43048 (17)0.08950 (13)0.0465 (5)
N30.3767 (3)0.5688 (4)0.1488 (2)0.1057 (12)
N40.0112 (4)0.0029 (3)0.1565 (2)0.1211 (14)
O10.26661 (18)0.38732 (17)0.26223 (12)0.0586 (5)
O20.24583 (18)0.61680 (15)0.24693 (11)0.0555 (5)
CO10.18236 (3)0.46551 (3)0.21245 (2)0.04969 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0650 (14)0.0425 (15)0.0427 (14)0.0144 (13)0.0106 (12)0.0201 (12)
C20.068 (2)0.0421 (15)0.0498 (16)0.0136 (13)0.0111 (14)0.0206 (13)
C30.074 (2)0.0530 (18)0.0533 (17)0.0214 (15)0.0070 (15)0.0296 (14)
C40.078 (2)0.0535 (17)0.0477 (16)0.0153 (15)0.0127 (15)0.0278 (14)
C50.071 (2)0.0628 (19)0.0530 (17)0.0158 (16)0.0174 (15)0.0315 (15)
C60.0666 (16)0.0554 (17)0.0505 (16)0.0163 (14)0.0141 (12)0.0287 (13)
C70.071 (2)0.066 (2)0.0652 (19)0.0236 (16)0.0148 (16)0.0361 (16)
C80.083 (2)0.074 (2)0.077 (2)0.0095 (19)0.0156 (19)0.0350 (19)
C90.097 (3)0.082 (3)0.090 (3)0.034 (2)0.031 (2)0.015 (2)
C100.091 (3)0.135 (4)0.125 (4)0.051 (3)0.031 (3)0.090 (3)
C110.111 (2)0.0800 (19)0.0583 (17)0.0217 (18)0.0234 (15)0.0449 (16)
C120.126 (3)0.085 (2)0.076 (2)0.027 (2)0.022 (2)0.053 (2)
C130.127 (3)0.096 (3)0.064 (2)0.026 (3)0.015 (2)0.045 (2)
C140.118 (3)0.100 (3)0.080 (3)0.025 (3)0.035 (2)0.054 (2)
C12A0.123 (3)0.093 (3)0.079 (2)0.024 (3)0.029 (2)0.054 (2)
C13A0.128 (3)0.092 (3)0.071 (2)0.027 (3)0.016 (2)0.050 (2)
C14A0.118 (3)0.099 (4)0.078 (3)0.029 (3)0.038 (3)0.053 (3)
C150.0612 (16)0.0652 (19)0.0501 (16)0.0156 (14)0.0145 (13)0.0291 (14)
C160.060 (2)0.0617 (18)0.0428 (14)0.0209 (15)0.0140 (13)0.0245 (13)
C170.065 (2)0.067 (2)0.0631 (19)0.0134 (17)0.0117 (16)0.0302 (16)
C180.061 (2)0.095 (3)0.068 (2)0.0235 (19)0.0130 (17)0.035 (2)
C190.066 (2)0.105 (3)0.0531 (18)0.042 (2)0.0182 (16)0.0343 (19)
C200.090 (3)0.079 (2)0.0600 (19)0.040 (2)0.0245 (17)0.0408 (17)
C210.063 (2)0.073 (2)0.0563 (17)0.0219 (16)0.0161 (15)0.0372 (16)
C220.128 (5)0.204 (6)0.199 (6)0.102 (4)0.050 (4)0.137 (5)
C230.079 (4)0.197 (6)0.216 (7)0.071 (4)0.035 (4)0.106 (5)
C240.0474 (16)0.0487 (16)0.0452 (15)0.0152 (12)0.0095 (12)0.0218 (13)
C250.0591 (19)0.0501 (17)0.0531 (17)0.0097 (14)0.0086 (14)0.0179 (14)
C260.093 (3)0.0420 (17)0.075 (2)0.0084 (16)0.0313 (19)0.0221 (16)
C270.112 (3)0.0514 (19)0.070 (2)0.0149 (18)0.041 (2)0.0295 (17)
C280.092 (2)0.0548 (19)0.0534 (17)0.0240 (16)0.0267 (16)0.0292 (15)
C290.0518 (17)0.0464 (16)0.0458 (15)0.0145 (12)0.0136 (12)0.0227 (12)
C300.0551 (17)0.0533 (17)0.0378 (13)0.0180 (13)0.0091 (12)0.0236 (12)
C310.091 (3)0.059 (2)0.0564 (19)0.0043 (18)0.0025 (18)0.0159 (16)
C320.121 (4)0.099 (3)0.083 (3)0.008 (3)0.039 (3)0.024 (2)
C330.139 (4)0.080 (3)0.063 (2)0.021 (2)0.042 (2)0.0110 (19)
C340.155 (4)0.063 (2)0.071 (2)0.002 (2)0.005 (3)0.004 (2)
C350.223 (5)0.079 (2)0.100 (3)0.025 (2)0.080 (3)0.056 (2)
C360.222 (5)0.080 (2)0.126 (3)0.027 (3)0.078 (3)0.063 (2)
C370.224 (5)0.087 (2)0.118 (3)0.031 (3)0.077 (3)0.070 (2)
C380.217 (5)0.089 (2)0.116 (3)0.026 (3)0.086 (3)0.066 (2)
C36A0.223 (5)0.084 (2)0.124 (3)0.029 (3)0.076 (3)0.067 (3)
C37A0.221 (5)0.090 (2)0.117 (3)0.028 (3)0.082 (3)0.068 (3)
C38A0.219 (5)0.085 (2)0.121 (3)0.024 (3)0.082 (3)0.066 (3)
C390.0624 (19)0.0498 (17)0.0451 (15)0.0113 (14)0.0098 (13)0.0225 (13)
C400.063 (2)0.0558 (19)0.0617 (19)0.0130 (15)0.0015 (15)0.0246 (15)
C410.081 (2)0.065 (2)0.063 (2)0.0063 (18)0.0075 (17)0.0180 (17)
C420.117 (3)0.052 (2)0.060 (2)0.004 (2)0.001 (2)0.0122 (17)
C430.162 (4)0.053 (2)0.080 (3)0.031 (2)0.013 (3)0.022 (2)
C440.122 (3)0.055 (2)0.063 (2)0.022 (2)0.017 (2)0.0209 (17)
C450.174 (5)0.098 (4)0.090 (3)0.009 (3)0.024 (3)0.018 (3)
C460.298 (14)0.053 (4)0.101 (7)0.046 (7)0.024 (8)0.025 (4)
C46A0.301 (14)0.057 (4)0.101 (7)0.039 (7)0.025 (7)0.025 (3)
N10.0582 (15)0.0523 (14)0.0473 (13)0.0157 (11)0.0083 (11)0.0251 (11)
N20.0561 (14)0.0433 (13)0.0424 (12)0.0138 (10)0.0055 (10)0.0192 (10)
N30.084 (3)0.154 (4)0.122 (3)0.067 (2)0.026 (2)0.085 (3)
N40.184 (4)0.057 (2)0.083 (2)0.001 (2)0.016 (2)0.0049 (18)
O10.0688 (13)0.0738 (14)0.0542 (11)0.0259 (10)0.0205 (10)0.0417 (10)
O20.0741 (14)0.0513 (11)0.0418 (10)0.0081 (9)0.0097 (9)0.0213 (9)
CO10.0632 (3)0.0506 (3)0.0427 (2)0.01369 (18)0.01155 (17)0.02546 (18)
Geometric parameters (Å, º) top
C1—O11.313 (3)C25—C311.527 (4)
C1—C61.417 (4)C26—C271.391 (5)
C1—C21.421 (4)C26—H260.9300
C2—C31.380 (4)C27—C281.362 (4)
C2—C71.535 (4)C27—C351.532 (5)
C3—C41.402 (4)C28—C291.415 (4)
C3—H30.9300C28—H280.9300
C4—C51.353 (4)C29—C301.428 (4)
C4—C111.524 (4)C30—N21.295 (3)
C5—C61.417 (4)C30—H300.9300
C5—H50.9300C31—C321.528 (5)
C6—C151.414 (4)C31—C331.540 (5)
C7—C91.513 (5)C31—C341.556 (5)
C7—C81.522 (4)C32—H32A0.9600
C7—C101.537 (5)C32—H32B0.9600
C8—H8A0.9600C32—H32C0.9600
C8—H8B0.9600C33—H33A0.9600
C8—H8C0.9600C33—H33B0.9600
C9—H9A0.9600C33—H33C0.9600
C9—H9B0.9600C34—H34A0.9600
C9—H9C0.9600C34—H34B0.9600
C10—H10A0.9600C34—H34C0.9600
C10—H10B0.9600C35—C37A1.459 (9)
C10—H10C0.9600C35—C361.468 (7)
C11—C13A1.512 (8)C35—C381.513 (7)
C11—C12A1.517 (8)C35—C36A1.514 (9)
C11—C141.530 (6)C35—C371.594 (7)
C11—C131.540 (6)C35—C38A1.599 (9)
C11—C14A1.547 (8)C36—H36A0.9600
C11—C121.551 (6)C36—H36B0.9600
C12—H12A0.9600C36—H36C0.9600
C12—H12B0.9600C37—H37A0.9600
C12—H12C0.9600C37—H37B0.9600
C13—H13A0.9600C37—H37C0.9600
C13—H13B0.9600C38—H38A0.9600
C13—H13C0.9600C38—H38B0.9600
C14—H14A0.9600C38—H38C0.9600
C14—H14B0.9600C36A—H36D0.9600
C14—H14C0.9600C36A—H36E0.9600
C12A—H12D0.9600C36A—H36F0.9600
C12A—H12E0.9600C37A—H37D0.9600
C12A—H12F0.9600C37A—H37E0.9600
C13A—H13D0.9600C37A—H37F0.9600
C13A—H13E0.9600C38A—H38D0.9600
C13A—H13F0.9600C38A—H38E0.9600
C14A—H14D0.9600C38A—H38F0.9600
C14A—H14E0.9600C39—C401.368 (4)
C14A—H14F0.9600C39—C441.381 (4)
C15—N11.307 (3)C39—N21.426 (3)
C15—H150.9300C40—C411.371 (4)
C16—C211.378 (4)C40—H400.9300
C16—C171.395 (4)C41—C421.381 (5)
C16—N11.428 (4)C41—H410.9300
C17—C181.347 (5)C42—C431.388 (5)
C17—H170.9300C42—N41.395 (4)
C18—C191.403 (5)C43—C441.369 (5)
C18—H180.9300C43—H430.9300
C19—N31.368 (4)C44—H440.9300
C19—C201.406 (5)C45—N41.439 (6)
C20—C211.372 (4)C45—H45A0.9600
C20—H200.9300C45—H45B0.9600
C21—H210.9300C45—H45C0.9600
C22—N31.372 (6)C46—N41.424 (10)
C22—H22A0.9600C46—H46A0.9600
C22—H22B0.9600C46—H46B0.9600
C22—H22C0.9600C46—H46C0.9600
C23—N31.437 (6)C46A—N41.445 (10)
C23—H23A0.9600C46A—H46D0.9600
C23—H23B0.9600C46A—H46E0.9600
C23—H23C0.9600C46A—H46F0.9600
C24—O21.300 (3)N1—CO11.980 (2)
C24—C251.418 (4)N2—CO11.984 (2)
C24—C291.425 (4)O1—CO11.8844 (19)
C25—C261.382 (4)O2—CO11.8882 (19)
O1—C1—C6121.6 (2)C27—C28—H28118.8
O1—C1—C2120.1 (3)C29—C28—H28118.8
C6—C1—C2118.2 (2)C28—C29—C24119.2 (3)
C3—C2—C1118.5 (3)C28—C29—C30116.0 (2)
C3—C2—C7121.0 (3)C24—C29—C30124.7 (2)
C1—C2—C7120.5 (2)N2—C30—C29128.7 (2)
C2—C3—C4124.5 (3)N2—C30—H30115.7
C2—C3—H3117.8C29—C30—H30115.7
C4—C3—H3117.8C25—C31—C32109.6 (3)
C5—C4—C3116.2 (3)C25—C31—C33109.7 (3)
C5—C4—C11124.0 (3)C32—C31—C33110.7 (3)
C3—C4—C11119.8 (3)C25—C31—C34111.2 (3)
C4—C5—C6123.2 (3)C32—C31—C34108.5 (3)
C4—C5—H5118.4C33—C31—C34107.1 (3)
C6—C5—H5118.4C31—C32—H32A109.5
C15—C6—C1125.3 (3)C31—C32—H32B109.5
C15—C6—C5115.4 (3)H32A—C32—H32B109.5
C1—C6—C5119.3 (3)C31—C32—H32C109.5
C9—C7—C8109.9 (3)H32A—C32—H32C109.5
C9—C7—C2109.9 (3)H32B—C32—H32C109.5
C8—C7—C2110.2 (3)C31—C33—H33A109.5
C9—C7—C10108.0 (3)C31—C33—H33B109.5
C8—C7—C10106.8 (3)H33A—C33—H33B109.5
C2—C7—C10112.0 (3)C31—C33—H33C109.5
C7—C8—H8A109.5H33A—C33—H33C109.5
C7—C8—H8B109.5H33B—C33—H33C109.5
H8A—C8—H8B109.5C31—C34—H34A109.5
C7—C8—H8C109.5C31—C34—H34B109.5
H8A—C8—H8C109.5H34A—C34—H34B109.5
H8B—C8—H8C109.5C31—C34—H34C109.5
C7—C9—H9A109.5H34A—C34—H34C109.5
C7—C9—H9B109.5H34B—C34—H34C109.5
H9A—C9—H9B109.5C36—C35—C38122.2 (6)
C7—C9—H9C109.5C37A—C35—C36A126.9 (10)
H9A—C9—H9C109.5C37A—C35—C27118.0 (6)
H9B—C9—H9C109.5C36—C35—C27117.0 (5)
C7—C10—H10A109.5C38—C35—C27107.6 (4)
C7—C10—H10B109.5C36A—C35—C27107.2 (6)
H10A—C10—H10B109.5C36—C35—C3797.9 (6)
C7—C10—H10C109.5C38—C35—C37102.5 (6)
H10A—C10—H10C109.5C27—C35—C37106.8 (4)
H10B—C10—H10C109.5C37A—C35—C38A102.2 (10)
C13A—C11—C12A110.5 (7)C36A—C35—C38A91.4 (9)
C13A—C11—C4114.1 (6)C27—C35—C38A104.6 (5)
C12A—C11—C4108.6 (5)C35—C36—H36A109.5
C4—C11—C14113.7 (3)C35—C36—H36B109.5
C4—C11—C13109.0 (4)H36A—C36—H36B109.5
C14—C11—C13108.3 (5)C35—C36—H36C109.5
C13A—C11—C14A105.7 (8)H36A—C36—H36C109.5
C12A—C11—C14A110.2 (7)H36B—C36—H36C109.5
C4—C11—C14A107.7 (5)C35—C37—H37A109.5
C4—C11—C12108.8 (3)C35—C37—H37B109.5
C14—C11—C12109.4 (4)H37A—C37—H37B109.5
C13—C11—C12107.5 (4)C35—C37—H37C109.5
C11—C12—H12A109.5H37A—C37—H37C109.5
C11—C12—H12B109.5H37B—C37—H37C109.5
H12A—C12—H12B109.5C35—C38—H38A109.5
C11—C12—H12C109.5C35—C38—H38B109.5
H12A—C12—H12C109.5H38A—C38—H38B109.5
H12B—C12—H12C109.5C35—C38—H38C109.5
C11—C13—H13A109.5H38A—C38—H38C109.5
C11—C13—H13B109.5H38B—C38—H38C109.5
H13A—C13—H13B109.5C35—C36A—H36D109.5
C11—C13—H13C109.5C35—C36A—H36E109.5
H13A—C13—H13C109.5H36D—C36A—H36E109.5
H13B—C13—H13C109.5C35—C36A—H36F109.5
C11—C14—H14A109.5H36D—C36A—H36F109.5
C11—C14—H14B109.5H36E—C36A—H36F109.5
H14A—C14—H14B109.5C35—C37A—H37D109.5
C11—C14—H14C109.5C35—C37A—H37E109.5
H14A—C14—H14C109.5H37D—C37A—H37E109.5
H14B—C14—H14C109.5C35—C37A—H37F109.5
C11—C12A—H12D109.5H37D—C37A—H37F109.5
C11—C12A—H12E109.5H37E—C37A—H37F109.5
H12D—C12A—H12E109.5C35—C38A—H38D109.5
C11—C12A—H12F109.5C35—C38A—H38E109.5
H12D—C12A—H12F109.5H38D—C38A—H38E109.5
H12E—C12A—H12F109.5C35—C38A—H38F109.5
C11—C13A—H13D109.5H38D—C38A—H38F109.5
C11—C13A—H13E109.5H38E—C38A—H38F109.5
H13D—C13A—H13E109.5C40—C39—C44117.7 (3)
C11—C13A—H13F109.5C40—C39—N2122.9 (3)
H13D—C13A—H13F109.5C44—C39—N2119.4 (3)
H13E—C13A—H13F109.5C39—C40—C41121.8 (3)
C11—C14A—H14D109.5C39—C40—H40119.1
C11—C14A—H14E109.5C41—C40—H40119.1
H14D—C14A—H14E109.5C40—C41—C42121.0 (3)
C11—C14A—H14F109.5C40—C41—H41119.5
H14D—C14A—H14F109.5C42—C41—H41119.5
H14E—C14A—H14F109.5C41—C42—C43116.9 (3)
N1—C15—C6129.0 (3)C41—C42—N4121.6 (4)
N1—C15—H15115.5C43—C42—N4121.4 (4)
C6—C15—H15115.5C44—C43—C42121.8 (3)
C21—C16—C17117.5 (3)C44—C43—H43119.1
C21—C16—N1119.0 (3)C42—C43—H43119.1
C17—C16—N1123.4 (3)C43—C44—C39120.7 (3)
C18—C17—C16121.7 (3)C43—C44—H44119.7
C18—C17—H17119.1C39—C44—H44119.7
C16—C17—H17119.1N4—C45—H45A109.5
C17—C18—C19121.8 (3)N4—C45—H45B109.5
C17—C18—H18119.1H45A—C45—H45B109.5
C19—C18—H18119.1N4—C45—H45C109.5
N3—C19—C18121.8 (4)H45A—C45—H45C109.5
N3—C19—C20121.9 (4)H45B—C45—H45C109.5
C18—C19—C20116.3 (3)N4—C46—H46A109.5
C21—C20—C19121.3 (3)N4—C46—H46B109.5
C21—C20—H20119.4H46A—C46—H46B109.5
C19—C20—H20119.4N4—C46—H46C109.5
C20—C21—C16121.3 (3)H46A—C46—H46C109.5
C20—C21—H21119.3H46B—C46—H46C109.5
C16—C21—H21119.3N4—C46A—H46D109.5
N3—C22—H22A109.5N4—C46A—H46E109.5
N3—C22—H22B109.5H46D—C46A—H46E109.5
H22A—C22—H22B109.5N4—C46A—H46F109.5
N3—C22—H22C109.5H46D—C46A—H46F109.5
H22A—C22—H22C109.5H46E—C46A—H46F109.5
H22B—C22—H22C109.5C15—N1—C16118.8 (2)
N3—C23—H23A109.5C15—N1—CO1118.8 (2)
N3—C23—H23B109.5C16—N1—CO1122.19 (18)
H23A—C23—H23B109.5C30—N2—C39117.2 (2)
N3—C23—H23C109.5C30—N2—CO1120.48 (18)
H23A—C23—H23C109.5C39—N2—CO1122.15 (17)
H23B—C23—H23C109.5C19—N3—C22122.3 (4)
O2—C24—C25119.9 (2)C19—N3—C23120.8 (4)
O2—C24—C29121.3 (2)C22—N3—C23116.5 (4)
C25—C24—C29118.7 (2)C42—N4—C45119.6 (4)
C26—C25—C24117.8 (3)C42—N4—C46A121.1 (5)
C26—C25—C31122.3 (3)C45—N4—C46A118.3 (6)
C24—C25—C31119.8 (3)C1—O1—CO1126.92 (18)
C25—C26—C27124.9 (3)C24—O2—CO1129.44 (17)
C25—C26—H26117.5O1—CO1—O2117.06 (9)
C27—C26—H26117.5O1—CO1—N196.23 (9)
C28—C27—C26116.9 (3)O2—CO1—N1112.64 (9)
C28—C27—C35121.2 (3)O1—CO1—N2119.77 (9)
C26—C27—C35121.9 (3)O2—CO1—N295.20 (8)
C27—C28—C29122.4 (3)N1—CO1—N2117.31 (9)
O1—C1—C2—C3178.0 (3)C25—C24—C29—C30178.6 (3)
C6—C1—C2—C32.5 (4)C28—C29—C30—N2174.1 (3)
O1—C1—C2—C73.1 (4)C24—C29—C30—N23.2 (5)
C6—C1—C2—C7176.4 (3)C26—C25—C31—C32116.3 (4)
C1—C2—C3—C41.6 (4)C24—C25—C31—C3262.8 (4)
C7—C2—C3—C4177.3 (3)C26—C25—C31—C33122.0 (4)
C2—C3—C4—C50.2 (5)C24—C25—C31—C3358.9 (4)
C2—C3—C4—C11179.6 (3)C26—C25—C31—C343.7 (5)
C3—C4—C5—C60.2 (5)C24—C25—C31—C34177.2 (3)
C11—C4—C5—C6180.0 (3)C28—C27—C35—C37A27.5 (11)
O1—C1—C6—C152.0 (5)C26—C27—C35—C37A152.6 (10)
C2—C1—C6—C15177.5 (3)C28—C27—C35—C36157.3 (7)
O1—C1—C6—C5178.3 (3)C26—C27—C35—C3622.6 (9)
C2—C1—C6—C52.2 (4)C28—C27—C35—C3860.5 (7)
C4—C5—C6—C15178.8 (3)C26—C27—C35—C38119.6 (6)
C4—C5—C6—C10.9 (5)C28—C27—C35—C36A123.7 (8)
C3—C2—C7—C9120.3 (3)C26—C27—C35—C36A56.2 (9)
C1—C2—C7—C960.8 (4)C28—C27—C35—C3748.9 (6)
C3—C2—C7—C8118.5 (3)C26—C27—C35—C37131.0 (5)
C1—C2—C7—C860.4 (3)C28—C27—C35—C38A140.2 (6)
C3—C2—C7—C100.2 (4)C26—C27—C35—C38A39.9 (7)
C1—C2—C7—C10179.1 (3)C44—C39—C40—C411.1 (5)
C5—C4—C11—C13A151.0 (7)N2—C39—C40—C41178.9 (3)
C3—C4—C11—C13A28.8 (8)C39—C40—C41—C420.8 (5)
C5—C4—C11—C12A85.3 (8)C40—C41—C42—C430.8 (6)
C3—C4—C11—C12A94.9 (8)C40—C41—C42—N4179.7 (4)
C5—C4—C11—C141.4 (6)C41—C42—C43—C441.1 (7)
C3—C4—C11—C14178.4 (4)N4—C42—C43—C44178.4 (4)
C5—C4—C11—C13122.3 (5)C42—C43—C44—C393.0 (7)
C3—C4—C11—C1357.6 (5)C40—C39—C44—C433.0 (6)
C5—C4—C11—C14A34.0 (8)N2—C39—C44—C43177.1 (4)
C3—C4—C11—C14A145.8 (7)C6—C15—N1—C16179.2 (3)
C5—C4—C11—C12120.8 (5)C6—C15—N1—CO15.0 (4)
C3—C4—C11—C1259.4 (5)C21—C16—N1—C15146.7 (3)
C1—C6—C15—N12.1 (5)C17—C16—N1—C1534.3 (4)
C5—C6—C15—N1177.6 (3)C21—C16—N1—CO129.0 (3)
C21—C16—C17—C181.9 (4)C17—C16—N1—CO1150.0 (2)
N1—C16—C17—C18179.1 (3)C29—C30—N2—C39179.9 (3)
C16—C17—C18—C191.3 (5)C29—C30—N2—CO14.9 (4)
C17—C18—C19—N3179.3 (3)C40—C39—N2—C3046.4 (4)
C17—C18—C19—C201.1 (5)C44—C39—N2—C30133.7 (3)
N3—C19—C20—C21178.8 (3)C40—C39—N2—CO1128.7 (3)
C18—C19—C20—C211.5 (5)C44—C39—N2—CO151.2 (4)
C19—C20—C21—C162.3 (5)C18—C19—N3—C22178.2 (4)
C17—C16—C21—C202.4 (4)C20—C19—N3—C221.4 (6)
N1—C16—C21—C20178.6 (3)C18—C19—N3—C235.4 (6)
O2—C24—C25—C26178.2 (3)C20—C19—N3—C23174.2 (4)
C29—C24—C25—C261.6 (4)C41—C42—N4—C455.4 (7)
O2—C24—C25—C310.9 (4)C43—C42—N4—C45175.1 (5)
C29—C24—C25—C31179.3 (3)C41—C42—N4—C46A162.7 (14)
C24—C25—C26—C270.7 (5)C43—C42—N4—C46A16.7 (15)
C31—C25—C26—C27179.8 (3)C6—C1—O1—CO113.7 (4)
C25—C26—C27—C280.4 (6)C2—C1—O1—CO1165.78 (19)
C25—C26—C27—C35179.6 (4)C25—C24—O2—CO1176.91 (19)
C26—C27—C28—C290.7 (5)C29—C24—O2—CO12.9 (4)
C35—C27—C28—C29179.4 (4)C1—O1—CO1—O2102.9 (2)
C27—C28—C29—C240.3 (5)C1—O1—CO1—N116.5 (2)
C27—C28—C29—C30177.7 (3)C1—O1—CO1—N2143.0 (2)
O2—C24—C29—C28178.4 (3)C24—O2—CO1—O1126.3 (2)
C25—C24—C29—C281.4 (4)C24—O2—CO1—N1123.5 (2)
O2—C24—C29—C301.3 (4)C24—O2—CO1—N21.1 (2)
Hydrogen-bond geometry (Å, º) top
Cg is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
C8—H8C···O10.962.383.007 (4)123
C9—H9A···O10.962.282.953 (4)126
C32—H32C···O20.962.332.974 (4)124
C33—H33C···O20.962.282.925 (4)124
C45—H45B···Cgi0.962.963.914 (5)171
Symmetry code: (i) x, y, z.
 

Acknowledgements

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

References

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