metal-organic compounds
Dibromidobis(3-bromobenzyl-κC)(4,7-diphenyl-1,10-phenanthroline-κ2N,N′)tin(IV)
aDepartment of Chemistry, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, Tamilnadu, India, bArignar Anna Government Arts College, Musiri, Tiruchirappalli 621 211, Tamilnadu, India, cDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, Tamilnadu, India, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: baskarvsp@gmail.com
In the title compound, [SnBr2(C7H6Br)2(C24H16N2)], the Sn atom is coordinated to a 4,7-diphenyl-1,10-phenanthroline, two 3-bromobenzyl and two bromide ligands, leading to a six-coordinate C2Br2N2 donor set. The bromobenzyl ligands are trans to each other, while the Br anions are in a cis arrangement. One of the two 3-bromobenzyl ligands is disordered over two similar conformations, with occupancies of 0.7078 (18) and 0.2922 (18). In the crystal, molecules are linked into centrosymmetric dimers by Br⋯Br halogen bonds [3.5972 (12) Å], which are linked into a supramolecular layer in the ac plane by weak intermolecular C—H⋯Br interactions.
CCDC reference: 1901922
Structure description
Organotin compounds are mostly known for their biocidal effects and have been used for multiple applications, being utilized as wood preservatives, acaricides, disinfectants, bactericides, fungicides, molluscicides, PVC stabilizers and marine antifouling products (Snoeij et al., 1987). In addition, much recent interest has focused on the potential applications of organotin compounds for their cytotoxicity and antitumour activities against various cell lines (Yadav et al., 2015; Varela-Ramirez et al., 2011). Metal complexes of 1,10-phenanthroline have also been found to show excellent biological activity, playing several roles, displaying both antimicrobial and antifungal activities (McCann et al., 2012a) and anticancer potential (McCann et al., 2012b). Several studies show that this ligand and a number of its complexes are effective against various strains of microorganisms (Josa Parada et al., 2017). Both diorgano- and triorganotin compounds have been confirmed to show cytotoxicity against various cancer cell lines (Yadav et al., 2015).
In light of these biological activities for both organotin compounds and metal complexes of phenanthroline derivatives, and the lack of such examples in the literature where both Sn and 4,7-diphenyl-1,10-phenanthroline were combined [the Cambridge Structural Database (CSD; Groom et al., 2016) gave two hits: (4,7-diphenyl-1,10-phenanthroline)dimethylbis(isothiocyanato)tin(IV) (Najafi et al., 2011) and di-n-butyl-dichlorido(4,7-diphenylphenanthroline)tin(IV) (Hu et al., 1989)], it was decided to synthesize and structurally characterize the title compound, (I). Its biological activity will be reported elsewhere.
In (I), the Sn atom is coordinated by a 4,7-diphenyl-1,10-phenanthroline, two 3-bromobenzyl and two bromide ligands, leading to a six-coordinate C2Br2N2 donor set (see Fig. 1). The bromobenzyl ligands are trans to each other, while the Br anions are in a cis arrangement. The geometry about the Sn atom is distorted octahedral due in part to the small bite distance of the 4,7-diphenyl-1,10-phenanthroline ligand. The cis angles range from 70.32 (11) to 94.2 (2)° and the trans angles range from 174.0 (3) to 161.60 (8)° (Table 1). One of the interesting aspects of the structure is the conformation adopted by the 3-bromobenzyl ligands. As indicated above, these are arranged in a trans fashion in the Sn coordination sphere. However, they are not arranged in the normal way to minimize steric repulsion, but rather are both tilted away from the SnN2Br2 plane, with a dihedral angle of 40.1 (2)° between them. The reason for this appears to be so that they can form intramolecular π–π interactions with the central phenanthroline moiety [Cg⋯Cg = 3.584 (2) and 3.694 (3) Å]. The 3-bromobenzyl rings and the phenanthroline ring are not mutually parallel, but make dihedral angles of 24.4 (2) and 21.7 (3)°. These values are about the closest these rings can approach each other while maintaining a tetrahedral (sp3) angle at the benzyl C atoms.
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As far as comparisons with related structures are concerned, there is only one other structure which bears some resemblance to (I), namely dibromobis(pentafluoroethyl)(1,10-phenanthroline)tin(IV), (II) (Klosener et al., 2017). The phenanthroline bite angle for (II) is 72.40 (9)°, which is slightly wider that the value found for (I) of 70.32 (11)°
In the crystal, molecules are linked into centrosymmetric dimers (Fig. 2) by Br⋯Br halogen bonds [Br3⋯Br4 = 3.5972 (12) Å] and the dimers are linked into a supramolecular layer in the ac plane by weak intermolecular C—H⋯Br interactions (Table 2 and Fig. 3).
Synthesis and crystallization
3-Bromobenzyl bromide, tin powder and 4,7-diphenyl-1,10-phenanthroline were purchased from Sigma–Aldrich and used without further purification. All solvents were dried according to standard procedures.
Synthesis of bis (3-bromobenzyl) tin dibromide. Tin powder (2 g, 16.8 mmol) and 3-bromobenzyl bromide (4.21 g, 16.8 mmol) in toluene (60 ml) were refluxed at 110 °C for 3 h. The crystallized products were extracted under vacuum, purified with chloroform and used for the synthesis of the complex.
Synthesis of dibromidobis(3-bromobenzyl)(4,7-diphenyl-1,10-phenanthroline)tin(IV), (I). Bis(3-bromobenzyl)tin dibromide (0.46 g, 0.752 mmol) in methanol (50 ml) was reacted with 4,7-diphenyl-1,10-phenanthroline (0.25 g, 0.752 mmol) at room temperature for 24 h. The yellow product was recrystallized by the vapour-diffusion method using chloroform as solvent and petroleum ether as antisolvent.
Refinement
Crystal data, data collection and structure . One of the two 3-bromobenzyl ligands is disordered over two similar conformations, with occupancies of 0.7078 (18) and 0.2929 (18), and were constrained to have similar geometries using the SAME command in SHELXL2018 (Sheldrick, 2015b). H atoms were idealized using a riding model, with Uiso(H) = 1.2Ueq(C). The maximum and minimum residual electron-density peaks of 1.14 and −1.47 Å−3, respectively, were located 0.71 and 0.77 Å from the C12 and Br3 atoms.
details are summarized in Table 3Structural data
CCDC reference: 1901922
https://doi.org/10.1107/S2414314619003365/tk4055sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619003365/tk4055Isup2.hkl
Data collection: APEX3 (Bruker, 2016); cell
APEX3/SAINT (Bruker, 2016); data reduction: SAINT/XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).[SnBr2(C7H6Br)2(C24H16N2)] | Z = 2 |
Mr = 950.95 | F(000) = 920 |
Triclinic, P1 | Dx = 1.824 Mg m−3 |
a = 10.1328 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.2430 (3) Å | Cell parameters from 9823 reflections |
c = 16.7726 (4) Å | θ = 3.0–28.6° |
α = 83.216 (2)° | µ = 5.38 mm−1 |
β = 72.639 (2)° | T = 296 K |
γ = 71.787 (1)° | Block, yellow |
V = 1731.72 (8) Å3 | 0.10 × 0.10 × 0.05 mm |
Bruker Kappa APEX3 CMOS diffractometer | 6920 reflections with I > 2σ(I) |
ω and φ scan | Rint = 0.056 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | θmax = 30.7°, θmin = 3.2° |
Tmin = 0.588, Tmax = 0.746 | h = −14→14 |
77114 measured reflections | k = −16→16 |
10637 independent reflections | l = −23→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0373P)2 + 5.1192P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
10637 reflections | Δρmax = 1.14 e Å−3 |
444 parameters | Δρmin = −1.47 e Å−3 |
342 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0039 (4) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Sn1 | 0.38752 (3) | 0.17331 (3) | 0.72938 (2) | 0.03379 (10) | |
Br1 | 0.33777 (7) | 0.02517 (5) | 0.63249 (4) | 0.06410 (18) | |
Br2 | 0.16984 (6) | 0.19942 (6) | 0.86610 (4) | 0.06052 (16) | |
N1 | 0.4864 (4) | 0.2968 (3) | 0.7817 (2) | 0.0308 (7) | |
N2 | 0.5998 (4) | 0.1939 (3) | 0.6302 (2) | 0.0341 (7) | |
C1 | 0.4282 (5) | 0.3489 (4) | 0.8548 (3) | 0.0366 (9) | |
H1A | 0.341361 | 0.336726 | 0.887668 | 0.044* | |
C2 | 0.4896 (5) | 0.4216 (4) | 0.8856 (3) | 0.0371 (9) | |
H2A | 0.442692 | 0.458385 | 0.937283 | 0.045* | |
C3 | 0.6184 (4) | 0.4389 (4) | 0.8402 (2) | 0.0319 (8) | |
C4 | 0.6838 (4) | 0.3835 (3) | 0.7609 (2) | 0.0298 (8) | |
C5 | 0.6128 (4) | 0.3139 (3) | 0.7340 (2) | 0.0281 (7) | |
C6 | 0.6732 (4) | 0.2596 (3) | 0.6529 (2) | 0.0286 (8) | |
C7 | 0.8030 (4) | 0.2756 (4) | 0.6007 (2) | 0.0328 (8) | |
C8 | 0.8698 (5) | 0.3509 (4) | 0.6294 (3) | 0.0410 (10) | |
H8A | 0.953686 | 0.365947 | 0.594406 | 0.049* | |
C9 | 0.8143 (5) | 0.4001 (4) | 0.7055 (3) | 0.0395 (10) | |
H9A | 0.862230 | 0.446305 | 0.722592 | 0.047* | |
C10 | 0.8584 (4) | 0.2214 (4) | 0.5210 (2) | 0.0347 (9) | |
C11 | 0.7795 (5) | 0.1564 (4) | 0.4997 (3) | 0.0426 (10) | |
H11A | 0.811934 | 0.120607 | 0.447548 | 0.051* | |
C12 | 0.6517 (5) | 0.1440 (4) | 0.5558 (3) | 0.0451 (11) | |
H12A | 0.600943 | 0.098914 | 0.540185 | 0.054* | |
C13 | 0.9940 (5) | 0.2357 (4) | 0.4614 (2) | 0.0357 (9) | |
C14 | 0.9906 (5) | 0.2837 (4) | 0.3814 (3) | 0.0440 (10) | |
H14A | 0.905237 | 0.304162 | 0.365872 | 0.053* | |
C15 | 1.1139 (6) | 0.3008 (5) | 0.3255 (3) | 0.0537 (12) | |
H15A | 1.111680 | 0.333651 | 0.272256 | 0.064* | |
C16 | 1.2389 (6) | 0.2699 (5) | 0.3477 (3) | 0.0570 (14) | |
H16A | 1.321496 | 0.283353 | 0.309874 | 0.068* | |
C17 | 1.2442 (5) | 0.2190 (5) | 0.4256 (4) | 0.0565 (13) | |
H17A | 1.330992 | 0.195671 | 0.439754 | 0.068* | |
C18 | 1.1215 (5) | 0.2023 (5) | 0.4826 (3) | 0.0469 (11) | |
H18A | 1.125085 | 0.168349 | 0.535556 | 0.056* | |
C19 | 0.6850 (5) | 0.5157 (4) | 0.8721 (2) | 0.0359 (9) | |
C20 | 0.8143 (6) | 0.4632 (5) | 0.8906 (3) | 0.0525 (12) | |
H20A | 0.862273 | 0.378558 | 0.881796 | 0.063* | |
C21 | 0.8736 (7) | 0.5360 (7) | 0.9224 (4) | 0.0700 (18) | |
H21A | 0.960660 | 0.499760 | 0.935713 | 0.084* | |
C22 | 0.8050 (8) | 0.6607 (7) | 0.9343 (4) | 0.077 (2) | |
H22A | 0.845981 | 0.709600 | 0.954680 | 0.092* | |
C23 | 0.6777 (8) | 0.7127 (6) | 0.9163 (4) | 0.0697 (18) | |
H23A | 0.631127 | 0.797693 | 0.924707 | 0.084* | |
C24 | 0.6150 (6) | 0.6415 (4) | 0.8855 (3) | 0.0481 (11) | |
H24A | 0.526526 | 0.678099 | 0.873946 | 0.058* | |
Br3 | 0.17356 (10) | 0.71660 (8) | 0.85740 (6) | 0.0998 (3) | |
C25 | 0.2648 (5) | 0.3378 (4) | 0.6683 (3) | 0.0419 (10) | |
H25A | 0.286528 | 0.321174 | 0.609603 | 0.050* | |
H25B | 0.162171 | 0.349458 | 0.693184 | 0.050* | |
C26 | 0.2978 (4) | 0.4559 (2) | 0.67555 (18) | 0.0470 (11) | |
C27 | 0.2270 (3) | 0.5234 (3) | 0.74818 (16) | 0.0504 (12) | |
H27A | 0.157510 | 0.496840 | 0.790011 | 0.060* | |
C28 | 0.2602 (4) | 0.6307 (3) | 0.75830 (17) | 0.0594 (14) | |
C29 | 0.3642 (4) | 0.6704 (3) | 0.6958 (2) | 0.0749 (19) | |
H29A | 0.386364 | 0.742139 | 0.702556 | 0.090* | |
C30 | 0.4349 (4) | 0.6028 (3) | 0.62315 (19) | 0.0682 (16) | |
H30A | 0.504435 | 0.629389 | 0.581319 | 0.082* | |
C31 | 0.4017 (4) | 0.4956 (3) | 0.61303 (16) | 0.0599 (14) | |
H31A | 0.449046 | 0.450363 | 0.564427 | 0.072* | |
Br4 | 0.74161 (13) | 0.12905 (11) | 0.99659 (6) | 0.0867 (4) | 0.7078 (18) |
C32 | 0.5264 (7) | 0.0032 (13) | 0.7775 (6) | 0.0418 (14) | 0.7078 (18) |
H32A | 0.467748 | −0.025946 | 0.828296 | 0.050* | 0.7078 (18) |
H32D | 0.559912 | −0.061825 | 0.736771 | 0.050* | 0.7078 (18) |
C33 | 0.6549 (4) | 0.0197 (5) | 0.7958 (2) | 0.0411 (12) | 0.7078 (18) |
C34 | 0.6406 (3) | 0.0586 (5) | 0.8744 (2) | 0.0452 (13) | 0.7078 (18) |
H34A | 0.552033 | 0.073368 | 0.914914 | 0.054* | 0.7078 (18) |
C35 | 0.7588 (4) | 0.0755 (5) | 0.8924 (2) | 0.0522 (14) | 0.7078 (18) |
C36 | 0.8912 (4) | 0.0534 (5) | 0.8319 (3) | 0.0576 (15) | 0.7078 (18) |
H36A | 0.970292 | 0.064717 | 0.843903 | 0.069* | 0.7078 (18) |
C37 | 0.9055 (4) | 0.0145 (5) | 0.7533 (2) | 0.0583 (16) | 0.7078 (18) |
H37A | 0.994127 | −0.000251 | 0.712761 | 0.070* | 0.7078 (18) |
C38 | 0.7874 (4) | −0.0024 (5) | 0.73526 (19) | 0.0489 (14) | 0.7078 (18) |
H38A | 0.796916 | −0.028410 | 0.682694 | 0.059* | 0.7078 (18) |
Br4' | 1.0330 (2) | 0.0096 (2) | 0.73285 (14) | 0.0682 (7) | 0.2922 (18) |
C32' | 0.4920 (14) | 0.010 (4) | 0.7812 (12) | 0.045 (3) | 0.2922 (18) |
H32B | 0.420210 | −0.019752 | 0.823919 | 0.054* | 0.2922 (18) |
H32C | 0.537565 | −0.051949 | 0.738235 | 0.054* | 0.2922 (18) |
C33' | 0.6043 (6) | 0.0184 (14) | 0.8195 (6) | 0.045 (2) | 0.2922 (18) |
C34' | 0.7443 (7) | 0.0041 (13) | 0.7687 (5) | 0.045 (2) | 0.2922 (18) |
H34B | 0.768330 | −0.016692 | 0.713079 | 0.054* | 0.2922 (18) |
C35' | 0.8483 (5) | 0.0208 (12) | 0.8011 (4) | 0.050 (2) | 0.2922 (18) |
C36' | 0.8124 (7) | 0.0519 (13) | 0.8843 (4) | 0.052 (2) | 0.2922 (18) |
H36B | 0.881969 | 0.063077 | 0.905934 | 0.063* | 0.2922 (18) |
C37' | 0.6724 (7) | 0.0662 (13) | 0.9350 (4) | 0.057 (2) | 0.2922 (18) |
H37B | 0.648295 | 0.086977 | 0.990655 | 0.069* | 0.2922 (18) |
C38' | 0.5683 (6) | 0.0495 (13) | 0.9026 (5) | 0.051 (2) | 0.2922 (18) |
H38B | 0.474636 | 0.059043 | 0.936589 | 0.061* | 0.2922 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.03763 (16) | 0.03340 (15) | 0.03712 (16) | −0.01548 (11) | −0.01446 (12) | −0.00210 (11) |
Br1 | 0.0924 (4) | 0.0533 (3) | 0.0721 (4) | −0.0312 (3) | −0.0480 (3) | −0.0061 (3) |
Br2 | 0.0514 (3) | 0.0794 (4) | 0.0558 (3) | −0.0348 (3) | −0.0020 (2) | −0.0114 (3) |
N1 | 0.0349 (17) | 0.0314 (17) | 0.0296 (16) | −0.0130 (14) | −0.0109 (14) | −0.0003 (13) |
N2 | 0.0368 (18) | 0.0363 (18) | 0.0328 (17) | −0.0127 (15) | −0.0096 (14) | −0.0088 (14) |
C1 | 0.035 (2) | 0.039 (2) | 0.039 (2) | −0.0182 (18) | −0.0082 (18) | 0.0038 (17) |
C2 | 0.039 (2) | 0.043 (2) | 0.030 (2) | −0.0129 (18) | −0.0060 (17) | −0.0088 (17) |
C3 | 0.039 (2) | 0.0291 (19) | 0.0292 (19) | −0.0091 (16) | −0.0122 (16) | −0.0048 (15) |
C4 | 0.035 (2) | 0.0280 (18) | 0.0278 (19) | −0.0086 (15) | −0.0092 (15) | −0.0062 (15) |
C5 | 0.0321 (19) | 0.0286 (18) | 0.0253 (18) | −0.0079 (15) | −0.0099 (15) | −0.0039 (14) |
C6 | 0.036 (2) | 0.0269 (18) | 0.0247 (18) | −0.0088 (15) | −0.0098 (15) | −0.0044 (14) |
C7 | 0.038 (2) | 0.034 (2) | 0.0267 (19) | −0.0104 (17) | −0.0086 (16) | −0.0049 (15) |
C8 | 0.042 (2) | 0.049 (3) | 0.034 (2) | −0.023 (2) | −0.0020 (18) | −0.0083 (19) |
C9 | 0.042 (2) | 0.045 (2) | 0.036 (2) | −0.023 (2) | −0.0018 (18) | −0.0116 (18) |
C10 | 0.038 (2) | 0.034 (2) | 0.028 (2) | −0.0054 (17) | −0.0073 (17) | −0.0040 (16) |
C11 | 0.046 (2) | 0.051 (3) | 0.032 (2) | −0.016 (2) | −0.0057 (19) | −0.0146 (19) |
C12 | 0.055 (3) | 0.038 (2) | 0.054 (3) | −0.017 (2) | −0.027 (2) | −0.008 (2) |
C13 | 0.041 (2) | 0.035 (2) | 0.028 (2) | −0.0105 (17) | −0.0029 (17) | −0.0089 (16) |
C14 | 0.049 (3) | 0.042 (2) | 0.038 (2) | −0.011 (2) | −0.010 (2) | −0.0022 (19) |
C15 | 0.064 (3) | 0.051 (3) | 0.040 (3) | −0.020 (2) | −0.003 (2) | 0.003 (2) |
C16 | 0.054 (3) | 0.055 (3) | 0.053 (3) | −0.022 (2) | 0.009 (2) | −0.013 (2) |
C17 | 0.039 (3) | 0.060 (3) | 0.067 (4) | −0.011 (2) | −0.009 (2) | −0.016 (3) |
C18 | 0.041 (2) | 0.052 (3) | 0.045 (3) | −0.008 (2) | −0.014 (2) | −0.005 (2) |
C19 | 0.045 (2) | 0.042 (2) | 0.0265 (19) | −0.0201 (19) | −0.0087 (17) | −0.0046 (16) |
C20 | 0.051 (3) | 0.067 (3) | 0.047 (3) | −0.020 (2) | −0.017 (2) | −0.016 (2) |
C21 | 0.060 (3) | 0.116 (5) | 0.053 (3) | −0.044 (4) | −0.017 (3) | −0.020 (3) |
C22 | 0.092 (5) | 0.114 (6) | 0.050 (3) | −0.075 (5) | −0.002 (3) | −0.027 (3) |
C23 | 0.107 (5) | 0.057 (3) | 0.052 (3) | −0.052 (3) | 0.002 (3) | −0.017 (3) |
C24 | 0.065 (3) | 0.043 (3) | 0.038 (2) | −0.023 (2) | −0.008 (2) | −0.0061 (19) |
Br3 | 0.1022 (6) | 0.0841 (5) | 0.1170 (7) | −0.0153 (4) | −0.0318 (5) | −0.0468 (5) |
C25 | 0.051 (3) | 0.038 (2) | 0.047 (3) | −0.016 (2) | −0.028 (2) | 0.0059 (19) |
C26 | 0.054 (3) | 0.039 (2) | 0.050 (3) | −0.008 (2) | −0.025 (2) | 0.006 (2) |
C27 | 0.055 (3) | 0.041 (3) | 0.060 (3) | −0.014 (2) | −0.027 (2) | 0.006 (2) |
C28 | 0.065 (3) | 0.044 (3) | 0.075 (4) | −0.006 (2) | −0.038 (3) | −0.003 (3) |
C29 | 0.088 (5) | 0.042 (3) | 0.108 (5) | −0.028 (3) | −0.046 (4) | 0.019 (3) |
C30 | 0.083 (4) | 0.061 (4) | 0.061 (4) | −0.027 (3) | −0.023 (3) | 0.020 (3) |
C31 | 0.076 (4) | 0.054 (3) | 0.053 (3) | −0.025 (3) | −0.021 (3) | 0.013 (2) |
Br4 | 0.1113 (9) | 0.1036 (8) | 0.0660 (6) | −0.0356 (6) | −0.0479 (6) | −0.0095 (5) |
C32 | 0.039 (3) | 0.032 (3) | 0.060 (3) | −0.008 (4) | −0.026 (3) | 0.000 (3) |
C33 | 0.043 (3) | 0.032 (2) | 0.054 (3) | −0.012 (2) | −0.022 (2) | 0.000 (2) |
C34 | 0.046 (3) | 0.042 (3) | 0.054 (3) | −0.012 (2) | −0.024 (2) | 0.003 (2) |
C35 | 0.055 (3) | 0.050 (3) | 0.060 (3) | −0.013 (3) | −0.030 (3) | −0.004 (3) |
C36 | 0.046 (3) | 0.059 (3) | 0.075 (4) | −0.013 (3) | −0.030 (3) | −0.003 (3) |
C37 | 0.041 (3) | 0.060 (3) | 0.071 (4) | −0.009 (3) | −0.016 (3) | −0.005 (3) |
C38 | 0.044 (3) | 0.043 (3) | 0.061 (3) | −0.007 (3) | −0.021 (3) | −0.006 (3) |
Br4' | 0.0440 (11) | 0.0825 (15) | 0.0820 (15) | −0.0203 (10) | −0.0192 (9) | −0.0073 (11) |
C32' | 0.043 (5) | 0.036 (5) | 0.062 (5) | −0.011 (6) | −0.025 (5) | 0.000 (5) |
C33' | 0.044 (4) | 0.036 (4) | 0.057 (4) | −0.009 (4) | −0.022 (3) | 0.002 (4) |
C34' | 0.043 (4) | 0.041 (4) | 0.056 (4) | −0.009 (4) | −0.023 (4) | 0.000 (4) |
C35' | 0.046 (4) | 0.047 (4) | 0.063 (4) | −0.011 (4) | −0.025 (3) | −0.001 (4) |
C36' | 0.050 (4) | 0.051 (4) | 0.062 (4) | −0.013 (4) | −0.026 (4) | −0.004 (4) |
C37' | 0.057 (5) | 0.058 (5) | 0.059 (5) | −0.010 (4) | −0.027 (4) | −0.003 (4) |
C38' | 0.049 (4) | 0.048 (4) | 0.057 (4) | −0.011 (4) | −0.023 (4) | 0.000 (4) |
Sn1—C32' | 2.05 (4) | C22—C23 | 1.347 (10) |
Sn1—C25 | 2.211 (4) | C22—H22A | 0.9300 |
Sn1—C32 | 2.218 (13) | C23—C24 | 1.387 (7) |
Sn1—N1 | 2.320 (3) | C23—H23A | 0.9300 |
Sn1—N2 | 2.353 (3) | C24—H24A | 0.9300 |
Sn1—Br2 | 2.6355 (6) | Br3—Br4i | 3.5972 (12) |
Sn1—Br1 | 2.7059 (5) | Br3—C28 | 1.856 (2) |
N1—C1 | 1.310 (5) | C25—C26 | 1.493 (4) |
N1—C5 | 1.350 (5) | C25—H25A | 0.9700 |
N2—C12 | 1.317 (6) | C25—H25B | 0.9700 |
N2—C6 | 1.351 (5) | C26—C27 | 1.3900 |
C1—C2 | 1.390 (6) | C26—C31 | 1.3900 |
C1—H1A | 0.9300 | C27—C28 | 1.3900 |
C2—C3 | 1.360 (6) | C27—H27A | 0.9300 |
C2—H2A | 0.9300 | C28—C29 | 1.3900 |
C3—C4 | 1.417 (5) | C29—C30 | 1.3900 |
C3—C19 | 1.477 (5) | C29—H29A | 0.9300 |
C4—C5 | 1.401 (5) | C30—C31 | 1.3900 |
C4—C9 | 1.424 (6) | C30—H30A | 0.9300 |
C5—C6 | 1.435 (5) | C31—H31A | 0.9300 |
C6—C7 | 1.398 (6) | Br4—C35 | 1.857 (2) |
C7—C10 | 1.415 (5) | C32—C33 | 1.492 (4) |
C7—C8 | 1.434 (6) | C32—H32A | 0.9700 |
C8—C9 | 1.339 (6) | C32—H32D | 0.9700 |
C8—H8A | 0.9300 | C33—C34 | 1.3900 |
C9—H9A | 0.9300 | C33—C38 | 1.3900 |
C10—C11 | 1.377 (6) | C34—C35 | 1.3900 |
C10—C13 | 1.481 (6) | C34—H34A | 0.9300 |
C11—C12 | 1.392 (7) | C35—C36 | 1.3900 |
C11—H11A | 0.9300 | C36—C37 | 1.3900 |
C12—H12A | 0.9300 | C36—H36A | 0.9300 |
C13—C18 | 1.370 (6) | C37—C38 | 1.3900 |
C13—C14 | 1.393 (6) | C37—H37A | 0.9300 |
C14—C15 | 1.373 (7) | C38—H38A | 0.9300 |
C14—H14A | 0.9300 | Br4'—C35' | 1.854 (3) |
C15—C16 | 1.356 (8) | C32'—C33' | 1.493 (4) |
C15—H15A | 0.9300 | C32'—H32B | 0.9700 |
C16—C17 | 1.372 (8) | C32'—H32C | 0.9700 |
C16—H16A | 0.9300 | C33'—C34' | 1.3900 |
C17—C18 | 1.375 (7) | C33'—C38' | 1.3900 |
C17—H17A | 0.9300 | C34'—C35' | 1.3900 |
C18—H18A | 0.9300 | C34'—H34B | 0.9300 |
C19—C20 | 1.370 (7) | C35'—C36' | 1.3900 |
C19—C24 | 1.380 (6) | C36'—C37' | 1.3900 |
C20—C21 | 1.385 (7) | C36'—H36B | 0.9300 |
C20—H20A | 0.9300 | C37'—C38' | 1.3900 |
C21—C22 | 1.365 (10) | C37'—H37B | 0.9300 |
C21—H21A | 0.9300 | C38'—H38B | 0.9300 |
C32'—Sn1—C25 | 174.2 (5) | C21—C20—H20A | 120.0 |
C25—Sn1—C32 | 174.0 (3) | C22—C21—C20 | 120.3 (6) |
C32'—Sn1—N1 | 94.2 (5) | C22—C21—H21A | 119.9 |
C25—Sn1—N1 | 91.65 (13) | C20—C21—H21A | 119.9 |
C32—Sn1—N1 | 89.8 (2) | C23—C22—C21 | 119.9 (5) |
C32'—Sn1—N2 | 94.0 (4) | C23—C22—H22A | 120.1 |
C25—Sn1—N2 | 88.03 (15) | C21—C22—H22A | 120.1 |
C32—Sn1—N2 | 87.0 (2) | C22—C23—C24 | 120.9 (6) |
N1—Sn1—N2 | 70.32 (11) | C22—C23—H23A | 119.5 |
C32'—Sn1—Br2 | 88.2 (4) | C24—C23—H23A | 119.5 |
C25—Sn1—Br2 | 91.60 (13) | C19—C24—C23 | 119.5 (5) |
C32—Sn1—Br2 | 94.2 (2) | C19—C24—H24A | 120.3 |
N1—Sn1—Br2 | 91.31 (8) | C23—C24—H24A | 120.3 |
N2—Sn1—Br2 | 161.60 (8) | C26—C25—Sn1 | 113.4 (3) |
C32'—Sn1—Br1 | 86.1 (5) | C26—C25—H25A | 108.9 |
C25—Sn1—Br1 | 88.35 (10) | Sn1—C25—H25A | 108.9 |
C32—Sn1—Br1 | 88.7 (2) | C26—C25—H25B | 108.9 |
N1—Sn1—Br1 | 164.19 (8) | Sn1—C25—H25B | 108.9 |
N2—Sn1—Br1 | 93.89 (8) | H25A—C25—H25B | 107.7 |
Br2—Sn1—Br1 | 104.49 (2) | C27—C26—C31 | 120.0 |
C1—N1—C5 | 118.5 (3) | C27—C26—C25 | 118.7 (3) |
C1—N1—Sn1 | 124.0 (3) | C31—C26—C25 | 121.3 (3) |
C5—N1—Sn1 | 117.5 (2) | C28—C27—C26 | 120.0 |
C12—N2—C6 | 118.9 (4) | C28—C27—H27A | 120.0 |
C12—N2—Sn1 | 124.4 (3) | C26—C27—H27A | 120.0 |
C6—N2—Sn1 | 116.7 (2) | C29—C28—C27 | 120.0 |
N1—C1—C2 | 123.3 (4) | C29—C28—Br3 | 119.64 (18) |
N1—C1—H1A | 118.4 | C27—C28—Br3 | 120.28 (18) |
C2—C1—H1A | 118.4 | C28—C29—C30 | 120.0 |
C3—C2—C1 | 120.0 (4) | C28—C29—H29A | 120.0 |
C3—C2—H2A | 120.0 | C30—C29—H29A | 120.0 |
C1—C2—H2A | 120.0 | C31—C30—C29 | 120.0 |
C2—C3—C4 | 117.8 (4) | C31—C30—H30A | 120.0 |
C2—C3—C19 | 120.7 (4) | C29—C30—H30A | 120.0 |
C4—C3—C19 | 121.5 (4) | C30—C31—C26 | 120.0 |
C5—C4—C3 | 118.3 (4) | C30—C31—H31A | 120.0 |
C5—C4—C9 | 118.3 (3) | C26—C31—H31A | 120.0 |
C3—C4—C9 | 123.3 (3) | C33—C32—Sn1 | 115.4 (8) |
N1—C5—C4 | 122.0 (3) | C33—C32—H32A | 108.4 |
N1—C5—C6 | 118.0 (3) | Sn1—C32—H32A | 108.4 |
C4—C5—C6 | 120.0 (3) | C33—C32—H32D | 108.4 |
N2—C6—C7 | 122.3 (3) | Sn1—C32—H32D | 108.4 |
N2—C6—C5 | 117.4 (3) | H32A—C32—H32D | 107.5 |
C7—C6—C5 | 120.3 (3) | C34—C33—C38 | 120.0 |
C6—C7—C10 | 118.5 (4) | C34—C33—C32 | 119.2 (3) |
C6—C7—C8 | 118.0 (3) | C38—C33—C32 | 120.8 (3) |
C10—C7—C8 | 123.5 (4) | C33—C34—C35 | 120.0 |
C9—C8—C7 | 121.6 (4) | C33—C34—H34A | 120.0 |
C9—C8—H8A | 119.2 | C35—C34—H34A | 120.0 |
C7—C8—H8A | 119.2 | C36—C35—C34 | 120.0 |
C8—C9—C4 | 121.8 (4) | C36—C35—Br4 | 119.3 (2) |
C8—C9—H9A | 119.1 | C34—C35—Br4 | 120.7 (2) |
C4—C9—H9A | 119.1 | C37—C36—C35 | 120.0 |
C11—C10—C7 | 117.5 (4) | C37—C36—H36A | 120.0 |
C11—C10—C13 | 120.7 (4) | C35—C36—H36A | 120.0 |
C7—C10—C13 | 121.8 (4) | C36—C37—C38 | 120.0 |
C10—C11—C12 | 120.4 (4) | C36—C37—H37A | 120.0 |
C10—C11—H11A | 119.8 | C38—C37—H37A | 120.0 |
C12—C11—H11A | 119.8 | C37—C38—C33 | 120.0 |
N2—C12—C11 | 122.4 (4) | C37—C38—H38A | 120.0 |
N2—C12—H12A | 118.8 | C33—C38—H38A | 120.0 |
C11—C12—H12A | 118.8 | C33'—C32'—Sn1 | 116 (2) |
C18—C13—C14 | 119.6 (4) | C33'—C32'—H32B | 108.3 |
C18—C13—C10 | 122.0 (4) | Sn1—C32'—H32B | 108.3 |
C14—C13—C10 | 118.4 (4) | C33'—C32'—H32C | 108.3 |
C15—C14—C13 | 119.7 (5) | Sn1—C32'—H32C | 108.3 |
C15—C14—H14A | 120.2 | H32B—C32'—H32C | 107.4 |
C13—C14—H14A | 120.2 | C34'—C33'—C38' | 120.0 |
C16—C15—C14 | 120.3 (5) | C34'—C33'—C32' | 118.7 (4) |
C16—C15—H15A | 119.8 | C38'—C33'—C32' | 121.1 (4) |
C14—C15—H15A | 119.8 | C33'—C34'—C35' | 120.0 |
C15—C16—C17 | 120.3 (5) | C33'—C34'—H34B | 120.0 |
C15—C16—H16A | 119.8 | C35'—C34'—H34B | 120.0 |
C17—C16—H16A | 119.8 | C36'—C35'—C34' | 120.0 |
C16—C17—C18 | 120.2 (5) | C36'—C35'—Br4' | 119.5 (3) |
C16—C17—H17A | 119.9 | C34'—C35'—Br4' | 120.4 (3) |
C18—C17—H17A | 119.9 | C37'—C36'—C35' | 120.0 |
C13—C18—C17 | 119.9 (5) | C37'—C36'—H36B | 120.0 |
C13—C18—H18A | 120.1 | C35'—C36'—H36B | 120.0 |
C17—C18—H18A | 120.1 | C36'—C37'—C38' | 120.0 |
C20—C19—C24 | 119.4 (4) | C36'—C37'—H37B | 120.0 |
C20—C19—C3 | 120.8 (4) | C38'—C37'—H37B | 120.0 |
C24—C19—C3 | 119.8 (4) | C37'—C38'—C33' | 120.0 |
C19—C20—C21 | 120.1 (5) | C37'—C38'—H38B | 120.0 |
C19—C20—H20A | 120.0 | C33'—C38'—H38B | 120.0 |
C5—N1—C1—C2 | 0.3 (6) | C14—C13—C18—C17 | 1.5 (7) |
Sn1—N1—C1—C2 | 179.3 (3) | C10—C13—C18—C17 | −179.1 (4) |
N1—C1—C2—C3 | −1.6 (7) | C16—C17—C18—C13 | 0.5 (8) |
C1—C2—C3—C4 | 1.5 (6) | C2—C3—C19—C20 | 115.5 (5) |
C1—C2—C3—C19 | −179.9 (4) | C4—C3—C19—C20 | −66.0 (6) |
C2—C3—C4—C5 | −0.2 (6) | C2—C3—C19—C24 | −63.0 (6) |
C19—C3—C4—C5 | −178.7 (4) | C4—C3—C19—C24 | 115.5 (5) |
C2—C3—C4—C9 | 176.5 (4) | C24—C19—C20—C21 | 0.0 (7) |
C19—C3—C4—C9 | −2.0 (6) | C3—C19—C20—C21 | −178.5 (5) |
C1—N1—C5—C4 | 1.1 (6) | C19—C20—C21—C22 | −1.0 (9) |
Sn1—N1—C5—C4 | −178.0 (3) | C20—C21—C22—C23 | 1.1 (9) |
C1—N1—C5—C6 | −178.1 (4) | C21—C22—C23—C24 | −0.2 (9) |
Sn1—N1—C5—C6 | 2.8 (4) | C20—C19—C24—C23 | 0.9 (7) |
C3—C4—C5—N1 | −1.2 (6) | C3—C19—C24—C23 | 179.4 (4) |
C9—C4—C5—N1 | −178.1 (4) | C22—C23—C24—C19 | −0.8 (8) |
C3—C4—C5—C6 | 178.0 (4) | Sn1—C25—C26—C27 | −82.9 (3) |
C9—C4—C5—C6 | 1.1 (6) | Sn1—C25—C26—C31 | 94.2 (3) |
C12—N2—C6—C7 | −0.6 (6) | C31—C26—C27—C28 | 0.0 |
Sn1—N2—C6—C7 | 178.2 (3) | C25—C26—C27—C28 | 177.1 (3) |
C12—N2—C6—C5 | 179.3 (4) | C26—C27—C28—C29 | 0.0 |
Sn1—N2—C6—C5 | −2.0 (5) | C26—C27—C28—Br3 | −176.7 (3) |
N1—C5—C6—N2 | −0.6 (5) | C27—C28—C29—C30 | 0.0 |
C4—C5—C6—N2 | −179.8 (4) | Br3—C28—C29—C30 | 176.7 (3) |
N1—C5—C6—C7 | 179.3 (3) | C28—C29—C30—C31 | 0.0 |
C4—C5—C6—C7 | 0.1 (6) | C29—C30—C31—C26 | 0.0 |
N2—C6—C7—C10 | 0.3 (6) | C27—C26—C31—C30 | 0.0 |
C5—C6—C7—C10 | −179.5 (4) | C25—C26—C31—C30 | −177.1 (3) |
N2—C6—C7—C8 | 177.7 (4) | Sn1—C32—C33—C34 | 88.1 (6) |
C5—C6—C7—C8 | −2.1 (6) | Sn1—C32—C33—C38 | −91.4 (5) |
C6—C7—C8—C9 | 3.1 (7) | C38—C33—C34—C35 | 0.0 |
C10—C7—C8—C9 | −179.7 (4) | C32—C33—C34—C35 | −179.5 (7) |
C7—C8—C9—C4 | −1.9 (7) | C33—C34—C35—C36 | 0.0 |
C5—C4—C9—C8 | −0.2 (7) | C33—C34—C35—Br4 | 179.3 (4) |
C3—C4—C9—C8 | −176.9 (4) | C34—C35—C36—C37 | 0.0 |
C6—C7—C10—C11 | 0.5 (6) | Br4—C35—C36—C37 | −179.4 (4) |
C8—C7—C10—C11 | −176.8 (4) | C35—C36—C37—C38 | 0.0 |
C6—C7—C10—C13 | 179.0 (4) | C36—C37—C38—C33 | 0.0 |
C8—C7—C10—C13 | 1.8 (6) | C34—C33—C38—C37 | 0.0 |
C7—C10—C11—C12 | −1.0 (7) | C32—C33—C38—C37 | 179.4 (8) |
C13—C10—C11—C12 | −179.6 (4) | Sn1—C32'—C33'—C34' | −86.4 (12) |
C6—N2—C12—C11 | 0.1 (7) | Sn1—C32'—C33'—C38' | 88.6 (14) |
Sn1—N2—C12—C11 | −178.6 (3) | C38'—C33'—C34'—C35' | 0.0 |
C10—C11—C12—N2 | 0.7 (7) | C32'—C33'—C34'—C35' | 175 (2) |
C11—C10—C13—C18 | −126.2 (5) | C33'—C34'—C35'—C36' | 0.0 |
C7—C10—C13—C18 | 55.2 (6) | C33'—C34'—C35'—Br4' | −177.0 (9) |
C11—C10—C13—C14 | 53.2 (6) | C34'—C35'—C36'—C37' | 0.0 |
C7—C10—C13—C14 | −125.3 (4) | Br4'—C35'—C36'—C37' | 177.0 (9) |
C18—C13—C14—C15 | −2.1 (7) | C35'—C36'—C37'—C38' | 0.0 |
C10—C13—C14—C15 | 178.5 (4) | C36'—C37'—C38'—C33' | 0.0 |
C13—C14—C15—C16 | 0.7 (7) | C34'—C33'—C38'—C37' | 0.0 |
C14—C15—C16—C17 | 1.3 (8) | C32'—C33'—C38'—C37' | −175 (2) |
C15—C16—C17—C18 | −1.9 (8) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···Br2 | 0.93 | 2.78 | 3.477 (4) | 133 |
C12—H12A···Br1 | 0.93 | 2.97 | 3.656 (5) | 132 |
C36—H36A···Br2ii | 0.93 | 3.00 | 3.883 (3) | 159 |
Symmetry code: (ii) x+1, y, z. |
Acknowledgements
The authors thank SAIF, IIT Madras, for providing the intensity data collection.
References
Bruker (2016). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Hu, S.-Z., Lin, W., Wan, J. & Huang, Z. (1989). Jiegou Huaxue (Chin. J. Struct. Chem.), 8, 36–42. CAS Google Scholar
Klosener, J., Wiesemann, M., Niemann, M., Neumann, B., Stammler, H.-G. & Hoge, B. (2017). Chem. Eur. J. 23, 8295–8298. Google Scholar
McCann, M., Kellett, A., Kavanagh, K., Devereux, M. & Santos, A. L. (2012a). Curr. Med. Chem. 19, 2703–2714. CrossRef CAS Google Scholar
McCann, M., Santos, A. L. S., da Silva, B. A., Romanos, M. T. V., Pyrrho, A. S., Devereux, M., Kavanagh, K., Fichtner, I. & Kellett, A. (2012b). Toxicol. Res. 1, 47–54. CrossRef CAS Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m244. CrossRef IUCr Journals Google Scholar
Parada, J., Ana, M. A., Guillermo, W. E. R. & Gino, C. (2017). J. Chil. Chem. Soc. 62, 3746–3751. CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Snoeij, N. J., Penninks, A. H. & Seinen, W. (1987). Environ. Res. 44, 335–353. CrossRef CAS Google Scholar
Varela-Ramirez, A., Costanzo, M., Carrasco, Y. P., Pannell, K. H. & Aguilera, R. J. (2011). Cell Biol. Toxicol. 27, 159–168. CAS Google Scholar
Yadav, S., Yousuf, I., Usman, M., Ahmad, M. F., Arjmanda, F. & Tabassum, S. (2015). RSC Adv. 5, 50673–50690. CrossRef CAS Google Scholar
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