research communications
κS)bromidobis(triphenylphosphane-κP)silver(I)
and Hirshfeld-surface analysis of (benzenecarbothioamide-aDepartment of Chemistry and Center of Excellence for Innovation in Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: chavengp@gmail.com
The title complex, [AgBr(C7H7NS)(C18H15P)2], was obtained from the reaction of silver(I) bromide with benzenecarbothioamide (C7H7NS) and triphenylphosphane (C18H15P) in the mixed solvent of acetonitrile and ethanol. The mononuclear complex exhibits a distorted tetrahedral coordination geometry about the metal atom, arising from one S atom of a benzenecarbothioamide ligand, two P atoms of two triphenylphosphane molecules and one bromide ion. An intramolecular N—H⋯Br hydrogen bond is observed and in the inversion dimers linked by pairs of N—H⋯Br and C—H⋯Br hydrogen bonds are observed. In addition, C—H⋯π interactions occur, leading to [101] chains. Hirshfeld-surface analyses are presented and discussed.
Keywords: crystal structure; AgI complex; benzenecarbothioamide; triphenylphosphane; hydrogen bonding; Hirshfeld surface; supramolecular interaction.
CCDC reference: 1484796
1. Chemical context
Mixed-ligand complexes of AgI-containing phosphorus and sulfur donor ligands have been studied and published extensively in recent years (Dennehy et al., 2007; Ruangwut & Pakawatchai, 2014) because of their potential ability to inhibit bacteria (Isab et al., 2010; Nawaz et al., 2011). Triphenylphosphane and thione ligands, which contain P and S donor atoms, respectively, are capable of forming mixed-ligand silver(I) complexes as mononuclear (Aslanidis et al., 1997) and dinuclear models (Cox et al., 2000). In this paper, we report the synthesis and structure of the mixed-ligand complex of silver(I) bromide with triphenylphosphane and benzenecarbothioamide ligands.
2. Structural commentary
The monomeric complex of the title compound crystallizes in the monoclinic P21/n, and is shown in Fig. 1. The silver ion is four-coordinated exhibiting a distorted tetrahedral environment. This deviation can be explained by P1—Ag1—P2 angle which has the highest value of 121.60 (2)° due to the and the repulsion between two bulky triphenylphosphane molecules. The range of angles around the Ag atom of 97.338 (18)–121.60 (2)° is similar to that observed in the analogous mononuclear silver(I) complex [AgCl(C7H7NS)(C18H15P)2] previously synthesized by us (Ruangwut & Pakawatchai, 2014), in which the angles about the metal ion are 97.298 (16)–120.053 (16)°. The Ag—S bond length of 2.6015 (8) Å is slightly longer than in [AgCl(C7H7NS)(C18H15P)2], 2.5580 (5) Å. The Ag—P bond lengths of 2.4682 (7) and 2.4671 (6) Å for Ag1—P1 and Ag1—P2, respectively, are similar to those of the Ag—P bond lengths in [AgCl(C7H7NS)(C18H15P)2] [2.4529 (5) and 2.4578 (5) Å], and similar to the Ag—P distances of analogous tetrahedrally coordinated AgI complexes such as [Ag(NO3)(C2H3N3S)(C18H15P)2] [2.4485 (6) and 2.4493 (6) Å; Wattanakanjana et al., 2014], [Ag(Htsa)(PPh3)3] [2.574 (7)–2.611 (6) Å; Nomiya et al., 1998] and [Ag(PPh3)2(bzoxtH)]·2NO3 [2.480 (1) and 2.514 (2) Å; McFarlane et al., 1998]. An intramolecular hydrogen bond N1—H1B⋯Br1 [3.413 (3) Å; Table 1] is found between one of the H atoms from an amine group of the benzenecarbothioamide molecule and the bromide ion, as depicted in Fig. 2, which also shows the inter-molecular dimeric hydrogen bonds.
3. Supramolecular features
In the crystal, the dimeric intermolecular interactions are generated through a crystallographic inversion center by linking through the N1—H1A⋯Br1i [3.357 (3)Å] and C17—H17⋯Br1i [3.789 (3) Å] [symmetry code: (i) 1 – x, 1 – y, 1 – z] hydrogen bonds between a pair of adjacent complex molecules; these are similar to the those in the above-mentioned complex [AgCl(C7H7NS)(C18H15P)2] (Ruangwut & Pakawatchai, 2014). There are two cyclic patterns of R42(8) loops formed by two pairs of N1—H1A⋯Br1 and N1—H1B⋯Br1 interactions and of R22(14) loops forming by a pair of C17—H17⋯Br1 interactions, as illustrated in Fig. 2. In addition, supramolecular C—H⋯π chains (Fig. 3) are formed between the Csp2 atoms of the phenyl rings and the centroids of another phenyl ring [C22—H22⋯Cg3 = 3.782 (3) Å].
4. Hirshfeld surface analysis
For the title complex, the Hirshfeld-surfaces analysis (McKinnon et al., 2004; Spackman & Jayatilaka, 2009) was generated by Crystal Explorer 3.1 (Wolff et al., 2012) and mapped over dnorm, de and di fingerprint plot (Spackman & McKinnon 2002; McKinnon et al., 2007). The contact distances to the closest atom inside (di) and outside (de) of the Hirshfeld surface analyse the intermolecular interactions via the mapping of dnorm, as depicted in Fig. 4. The interactions are shown on the Hirshfeld surfaces with short contacts indicated in red. The corresponding fingerprint plots (Fig. 5a–d) for Hirshfeld surfaces of the complex are shown with characteristic pseudo-symmetry wings in the upper left and lower right sides of the de and di diagonal axes that represent the overall 2D fingerprint plot and those delineated into H⋯H, H⋯Br/Br⋯H, and C⋯H/H⋯C contacts are shown in Fig. 5a–d, respectively. The fingerprint plot of H⋯H contacts represented by the largest contribution within the Hirshfeld surfaces (60.8%) are shown as one distinct pattern with a minimum value of de + di ∼2.6 Å. The reciprocal H⋯Br/Br⋯H contacts consist of 5.4% of the total Hirshfeld surface with de + di ∼3.3 Å, exhibited by two symmetrical narrow pointed wings indicating the intermolecular hydrogen-bond interactions N1—H1A⋯Br1 and C17—H17⋯Br1 in the crystal packing. The presence of C—H⋯π interactions on the fingerprint plot, which contribute 29.7% of overall Hirshfeld surface, are indicated by de + di ∼3.0 Å.
5. Synthesis and crystallization
Silver(I) bromide (0.10 g, 0.5 mmol) was dissolved in the mixed solvent of 15 ml of acetonitrile and 15 ml of ethanol and then triphenylphosphane (0.27 g, 1 mmol) was added. The mixture was refluxed for 2 h at 343 K and a white precipitate was formed. After that, benzenecarbothioamide (0.13 g, 1 mmol) was added and continually refluxed for 5 h. At that time, the white precipitate dissolved. The clear yellow solution was filtered and left to evaporate at room temperature. After a day, pale-yellow blocks of the title compound were filtered off and dried in vacuo. Calculated for C43H37AgBrNP2S: C 61.07, H 4.37, N 1.65 and S 3.78%. Found: C 60.50, H 4.21, N 1.43 and S 3.70%.
6. Refinement
Crystal data and details of . All H atoms on carbon atoms were positioned geometrically and refined using a riding-model approximation with C—H = 0.93 Å with Uiso(H) = 1.2 Ueq(C). N-bound H atoms were found from difference maps and refined isotropically with distance restraint N—H = 0.85–0.86 Å.
are summarized in Table 2Supporting information
CCDC reference: 1484796
https://doi.org/10.1107/S2056989016009518/hb7592sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016009518/hb7592Isup2.hkl
Data collection: SMART (Bruker, 2003); cell
SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012) and publCIF (Westrip, 2010).[AgBr(C7H7NS)(C18H15P)2] | F(000) = 1720 |
Mr = 849.51 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 14.4354 (5) Å | Cell parameters from 7218 reflections |
b = 14.1925 (5) Å | θ = 2.4–22.5° |
c = 19.1682 (6) Å | µ = 1.72 mm−1 |
β = 98.786 (1)° | T = 293 K |
V = 3881.0 (2) Å3 | Block, pale yellow |
Z = 4 | 0.23 × 0.13 × 0.08 mm |
Bruker APEX CCD area-detector diffractometer | 6704 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Frames, each covering 0.3 ° in ω scans | θmax = 27.9°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −18→18 |
Tmin = 0.885, Tmax = 1.000 | k = −18→18 |
52150 measured reflections | l = −25→25 |
9261 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | Hydrogen site location: mixed |
wR(F2) = 0.085 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.3053P] where P = (Fo2 + 2Fc2)/3 |
9261 reflections | (Δ/σ)max = 0.002 |
450 parameters | Δρmax = 0.47 e Å−3 |
2 restraints | Δρmin = −0.24 e Å−3 |
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 | ||
Ag1 | 0.46287 (2) | 0.62099 (2) | 0.69031 (2) | 0.04396 (7) | |
Br1 | 0.58251 (2) | 0.50868 (2) | 0.63144 (2) | 0.05659 (9) | |
P2 | 0.48182 (4) | 0.57124 (5) | 0.81500 (3) | 0.03691 (15) | |
P1 | 0.52341 (5) | 0.77367 (5) | 0.65520 (3) | 0.03869 (15) | |
S1 | 0.29135 (5) | 0.58599 (6) | 0.63246 (4) | 0.0582 (2) | |
N1 | 0.36464 (19) | 0.50017 (19) | 0.53303 (13) | 0.0570 (6) | |
C31 | 0.46028 (17) | 0.44578 (18) | 0.82667 (13) | 0.0400 (6) | |
C13 | 0.52381 (17) | 0.79219 (17) | 0.56084 (13) | 0.0400 (6) | |
C19 | 0.59722 (17) | 0.58766 (17) | 0.86800 (13) | 0.0398 (6) | |
C25 | 0.40173 (17) | 0.63235 (18) | 0.86506 (13) | 0.0418 (6) | |
C1 | 0.64521 (18) | 0.78817 (18) | 0.69490 (14) | 0.0446 (6) | |
C7 | 0.46305 (18) | 0.87882 (18) | 0.68001 (13) | 0.0431 (6) | |
C38 | 0.20344 (19) | 0.5373 (2) | 0.49980 (13) | 0.0479 (6) | |
C8 | 0.5067 (2) | 0.95988 (19) | 0.70832 (14) | 0.0496 (7) | |
H8 | 0.5717 | 0.9634 | 0.7165 | 0.059* | |
C14 | 0.5523 (2) | 0.87597 (18) | 0.53392 (15) | 0.0505 (7) | |
H14 | 0.5707 | 0.9259 | 0.5643 | 0.061* | |
C37 | 0.29051 (18) | 0.53868 (19) | 0.55164 (13) | 0.0438 (6) | |
C26 | 0.3653 (2) | 0.5943 (2) | 0.92112 (15) | 0.0575 (7) | |
H26 | 0.3812 | 0.5330 | 0.9354 | 0.069* | |
C18 | 0.4949 (2) | 0.7197 (2) | 0.51477 (14) | 0.0567 (8) | |
H18 | 0.4745 | 0.6633 | 0.5319 | 0.068* | |
C36 | 0.4922 (2) | 0.39729 (19) | 0.88842 (15) | 0.0527 (7) | |
H36 | 0.5274 | 0.4286 | 0.9261 | 0.063* | |
C15 | 0.5538 (2) | 0.8863 (2) | 0.46293 (16) | 0.0570 (8) | |
H15 | 0.5739 | 0.9427 | 0.4456 | 0.068* | |
C32 | 0.4108 (2) | 0.39653 (19) | 0.77074 (15) | 0.0533 (7) | |
H32 | 0.3904 | 0.4272 | 0.7283 | 0.064* | |
C9 | 0.4535 (3) | 1.0364 (2) | 0.72469 (15) | 0.0627 (8) | |
H9 | 0.4832 | 1.0904 | 0.7444 | 0.075* | |
C30 | 0.3763 (2) | 0.7235 (2) | 0.84460 (17) | 0.0589 (8) | |
H30 | 0.3992 | 0.7501 | 0.8063 | 0.071* | |
C6 | 0.7174 (2) | 0.7775 (2) | 0.65652 (18) | 0.0662 (8) | |
H6 | 0.7044 | 0.7668 | 0.6081 | 0.079* | |
C35 | 0.4722 (2) | 0.3025 (2) | 0.89437 (16) | 0.0629 (8) | |
H35 | 0.4934 | 0.2708 | 0.9362 | 0.075* | |
C20 | 0.6114 (2) | 0.6257 (2) | 0.93455 (15) | 0.0625 (8) | |
H20 | 0.5601 | 0.6456 | 0.9547 | 0.075* | |
C16 | 0.5258 (2) | 0.8140 (2) | 0.41780 (15) | 0.0638 (8) | |
H16 | 0.5267 | 0.8212 | 0.3697 | 0.077* | |
C34 | 0.4216 (2) | 0.2551 (2) | 0.83930 (18) | 0.0647 (8) | |
H34 | 0.4078 | 0.1916 | 0.8437 | 0.078* | |
C12 | 0.3662 (2) | 0.8761 (2) | 0.66785 (19) | 0.0675 (9) | |
H12 | 0.3354 | 0.8221 | 0.6490 | 0.081* | |
C22 | 0.7760 (2) | 0.6065 (2) | 0.9435 (2) | 0.0730 (10) | |
H22 | 0.8361 | 0.6122 | 0.9689 | 0.088* | |
C17 | 0.4962 (3) | 0.7304 (2) | 0.44316 (16) | 0.0703 (9) | |
H17 | 0.4772 | 0.6812 | 0.4123 | 0.084* | |
C33 | 0.3916 (2) | 0.3018 (2) | 0.77778 (18) | 0.0676 (9) | |
H33 | 0.3577 | 0.2695 | 0.7400 | 0.081* | |
C43 | 0.1355 (2) | 0.6041 (3) | 0.50190 (18) | 0.0769 (11) | |
H43 | 0.1446 | 0.6509 | 0.5363 | 0.092* | |
C27 | 0.3056 (2) | 0.6455 (3) | 0.95658 (19) | 0.0755 (10) | |
H27 | 0.2818 | 0.6189 | 0.9945 | 0.091* | |
C24 | 0.6743 (2) | 0.5599 (2) | 0.83923 (16) | 0.0646 (8) | |
H24 | 0.6667 | 0.5344 | 0.7940 | 0.077* | |
C28 | 0.2820 (2) | 0.7350 (3) | 0.9356 (2) | 0.0835 (11) | |
H28 | 0.2413 | 0.7693 | 0.9592 | 0.100* | |
C39 | 0.1878 (2) | 0.4692 (2) | 0.44791 (17) | 0.0699 (9) | |
H39 | 0.2329 | 0.4232 | 0.4450 | 0.084* | |
C2 | 0.6671 (2) | 0.8013 (2) | 0.76686 (15) | 0.0621 (8) | |
H2 | 0.6190 | 0.8066 | 0.7939 | 0.075* | |
C3 | 0.7590 (3) | 0.8066 (3) | 0.7994 (2) | 0.0811 (11) | |
H3 | 0.7727 | 0.8166 | 0.8478 | 0.097* | |
C29 | 0.3173 (2) | 0.7755 (3) | 0.8803 (2) | 0.0775 (10) | |
H29 | 0.3019 | 0.8372 | 0.8669 | 0.093* | |
C23 | 0.7633 (2) | 0.5695 (3) | 0.8772 (2) | 0.0807 (11) | |
H23 | 0.8151 | 0.5505 | 0.8573 | 0.097* | |
C21 | 0.7004 (2) | 0.6350 (3) | 0.97230 (18) | 0.0788 (10) | |
H21 | 0.7085 | 0.6608 | 1.0174 | 0.095* | |
C4 | 0.8294 (3) | 0.7974 (3) | 0.7605 (2) | 0.0887 (12) | |
H4 | 0.8914 | 0.8012 | 0.7823 | 0.106* | |
C10 | 0.3588 (3) | 1.0325 (3) | 0.71206 (19) | 0.0775 (11) | |
H10 | 0.3236 | 1.0839 | 0.7228 | 0.093* | |
C41 | 0.0393 (3) | 0.5356 (3) | 0.40405 (18) | 0.0859 (12) | |
H41 | −0.0162 | 0.5347 | 0.3722 | 0.103* | |
C11 | 0.3150 (3) | 0.9533 (3) | 0.6836 (2) | 0.0874 (12) | |
H11 | 0.2499 | 0.9512 | 0.6746 | 0.105* | |
C5 | 0.8099 (2) | 0.7825 (3) | 0.6898 (2) | 0.0874 (11) | |
H5 | 0.8586 | 0.7757 | 0.6636 | 0.105* | |
C40 | 0.1056 (3) | 0.4688 (3) | 0.4003 (2) | 0.0889 (12) | |
H40 | 0.0957 | 0.4226 | 0.3656 | 0.107* | |
C42 | 0.0537 (3) | 0.6035 (3) | 0.4541 (2) | 0.0978 (14) | |
H42 | 0.0085 | 0.6497 | 0.4562 | 0.117* | |
H1A | 0.370 (2) | 0.485 (2) | 0.4908 (7) | 0.064 (10)* | |
H1B | 0.4142 (14) | 0.498 (2) | 0.5637 (13) | 0.071 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.05487 (13) | 0.04402 (12) | 0.03328 (10) | −0.00277 (9) | 0.00765 (8) | 0.00067 (8) |
Br1 | 0.06087 (19) | 0.06224 (19) | 0.04602 (16) | 0.01813 (14) | 0.00608 (13) | −0.00806 (13) |
P2 | 0.0384 (4) | 0.0428 (4) | 0.0294 (3) | −0.0038 (3) | 0.0046 (3) | −0.0006 (3) |
P1 | 0.0405 (4) | 0.0387 (4) | 0.0364 (3) | −0.0011 (3) | 0.0043 (3) | 0.0022 (3) |
S1 | 0.0462 (4) | 0.0899 (6) | 0.0381 (4) | 0.0004 (4) | 0.0049 (3) | −0.0146 (4) |
N1 | 0.0511 (16) | 0.0765 (18) | 0.0416 (15) | 0.0049 (13) | 0.0016 (12) | −0.0149 (13) |
C31 | 0.0390 (14) | 0.0432 (14) | 0.0395 (14) | −0.0028 (11) | 0.0117 (11) | −0.0001 (11) |
C13 | 0.0413 (14) | 0.0394 (14) | 0.0392 (13) | 0.0008 (11) | 0.0056 (11) | 0.0026 (11) |
C19 | 0.0410 (14) | 0.0418 (13) | 0.0357 (13) | −0.0033 (11) | 0.0032 (11) | 0.0038 (11) |
C25 | 0.0335 (13) | 0.0524 (16) | 0.0381 (13) | −0.0018 (11) | 0.0009 (10) | −0.0091 (11) |
C1 | 0.0417 (15) | 0.0399 (14) | 0.0508 (16) | −0.0016 (11) | 0.0031 (12) | 0.0019 (12) |
C7 | 0.0475 (15) | 0.0438 (15) | 0.0387 (14) | 0.0029 (12) | 0.0090 (11) | 0.0079 (11) |
C38 | 0.0470 (16) | 0.0564 (17) | 0.0388 (15) | −0.0034 (13) | 0.0017 (12) | −0.0017 (12) |
C8 | 0.0599 (18) | 0.0475 (16) | 0.0412 (15) | 0.0022 (14) | 0.0076 (13) | 0.0020 (12) |
C14 | 0.0604 (18) | 0.0443 (15) | 0.0478 (16) | −0.0077 (13) | 0.0111 (13) | −0.0001 (12) |
C37 | 0.0480 (16) | 0.0474 (15) | 0.0358 (13) | −0.0048 (12) | 0.0062 (11) | −0.0004 (11) |
C26 | 0.0495 (17) | 0.076 (2) | 0.0486 (17) | 0.0003 (15) | 0.0137 (13) | −0.0011 (15) |
C18 | 0.081 (2) | 0.0434 (16) | 0.0426 (16) | −0.0081 (14) | −0.0016 (14) | 0.0039 (12) |
C36 | 0.0664 (19) | 0.0514 (17) | 0.0409 (15) | −0.0057 (14) | 0.0105 (13) | 0.0014 (12) |
C15 | 0.069 (2) | 0.0506 (17) | 0.0537 (18) | −0.0045 (14) | 0.0185 (15) | 0.0128 (14) |
C32 | 0.0589 (18) | 0.0466 (17) | 0.0518 (17) | −0.0013 (13) | −0.0006 (14) | −0.0021 (13) |
C9 | 0.099 (3) | 0.0502 (18) | 0.0401 (16) | 0.0130 (17) | 0.0152 (16) | 0.0038 (13) |
C30 | 0.0547 (18) | 0.0578 (19) | 0.0644 (19) | 0.0051 (14) | 0.0103 (15) | −0.0063 (15) |
C6 | 0.0484 (18) | 0.083 (2) | 0.067 (2) | 0.0052 (16) | 0.0095 (15) | −0.0037 (17) |
C35 | 0.086 (2) | 0.0514 (18) | 0.0558 (18) | 0.0008 (16) | 0.0264 (17) | 0.0143 (15) |
C20 | 0.0428 (16) | 0.094 (2) | 0.0492 (17) | −0.0026 (16) | 0.0020 (13) | −0.0187 (16) |
C16 | 0.088 (2) | 0.067 (2) | 0.0371 (15) | 0.0064 (18) | 0.0116 (15) | 0.0091 (15) |
C34 | 0.075 (2) | 0.0433 (17) | 0.080 (2) | −0.0069 (15) | 0.0283 (18) | −0.0005 (16) |
C12 | 0.0484 (18) | 0.0524 (18) | 0.102 (3) | 0.0035 (15) | 0.0115 (17) | 0.0094 (17) |
C22 | 0.0412 (18) | 0.090 (3) | 0.081 (3) | −0.0003 (17) | −0.0120 (16) | 0.005 (2) |
C17 | 0.112 (3) | 0.0534 (19) | 0.0414 (16) | −0.0049 (18) | −0.0030 (17) | −0.0042 (14) |
C33 | 0.075 (2) | 0.0524 (19) | 0.072 (2) | −0.0125 (16) | 0.0024 (17) | −0.0101 (16) |
C43 | 0.074 (2) | 0.093 (3) | 0.057 (2) | 0.022 (2) | −0.0118 (17) | −0.0258 (18) |
C27 | 0.055 (2) | 0.107 (3) | 0.069 (2) | −0.001 (2) | 0.0270 (17) | −0.015 (2) |
C24 | 0.0506 (18) | 0.085 (2) | 0.0585 (19) | 0.0097 (17) | 0.0088 (15) | −0.0137 (17) |
C28 | 0.057 (2) | 0.107 (3) | 0.088 (3) | 0.007 (2) | 0.019 (2) | −0.039 (2) |
C39 | 0.068 (2) | 0.071 (2) | 0.066 (2) | 0.0066 (17) | −0.0053 (16) | −0.0185 (17) |
C2 | 0.0574 (19) | 0.073 (2) | 0.0520 (18) | −0.0008 (16) | −0.0031 (14) | 0.0007 (15) |
C3 | 0.076 (3) | 0.085 (3) | 0.072 (2) | −0.008 (2) | −0.022 (2) | −0.0021 (19) |
C29 | 0.065 (2) | 0.068 (2) | 0.097 (3) | 0.0170 (18) | 0.006 (2) | −0.018 (2) |
C23 | 0.0428 (18) | 0.110 (3) | 0.089 (3) | 0.0174 (19) | 0.0091 (17) | −0.007 (2) |
C21 | 0.059 (2) | 0.111 (3) | 0.060 (2) | −0.005 (2) | −0.0114 (16) | −0.0200 (19) |
C4 | 0.051 (2) | 0.091 (3) | 0.115 (4) | −0.007 (2) | −0.019 (2) | 0.002 (2) |
C10 | 0.101 (3) | 0.065 (2) | 0.076 (2) | 0.036 (2) | 0.040 (2) | 0.0163 (18) |
C41 | 0.064 (2) | 0.128 (3) | 0.057 (2) | 0.006 (2) | −0.0167 (17) | −0.015 (2) |
C11 | 0.058 (2) | 0.082 (3) | 0.128 (3) | 0.022 (2) | 0.031 (2) | 0.020 (2) |
C5 | 0.045 (2) | 0.108 (3) | 0.111 (3) | 0.0058 (19) | 0.017 (2) | 0.005 (3) |
C40 | 0.083 (3) | 0.101 (3) | 0.072 (2) | 0.000 (2) | −0.020 (2) | −0.035 (2) |
C42 | 0.082 (3) | 0.130 (4) | 0.071 (2) | 0.043 (2) | −0.021 (2) | −0.027 (2) |
Ag1—P2 | 2.4671 (6) | C30—H30 | 0.9300 |
Ag1—P1 | 2.4682 (7) | C6—C5 | 1.391 (5) |
Ag1—S1 | 2.6015 (8) | C6—H6 | 0.9300 |
Ag1—Br1 | 2.7189 (3) | C35—C34 | 1.365 (4) |
P2—C31 | 1.827 (3) | C35—H35 | 0.9300 |
P2—C19 | 1.829 (2) | C20—C21 | 1.381 (4) |
P2—C25 | 1.830 (3) | C20—H20 | 0.9300 |
P1—C1 | 1.818 (3) | C16—C17 | 1.374 (4) |
P1—C7 | 1.827 (3) | C16—H16 | 0.9300 |
P1—C13 | 1.828 (2) | C34—C33 | 1.364 (4) |
S1—C37 | 1.687 (3) | C34—H34 | 0.9300 |
N1—C37 | 1.299 (4) | C12—C11 | 1.380 (5) |
N1—H1A | 0.852 (10) | C12—H12 | 0.9300 |
N1—H1B | 0.854 (10) | C22—C21 | 1.358 (5) |
C31—C32 | 1.383 (3) | C22—C23 | 1.361 (5) |
C31—C36 | 1.386 (3) | C22—H22 | 0.9300 |
C13—C18 | 1.378 (4) | C17—H17 | 0.9300 |
C13—C14 | 1.384 (3) | C33—H33 | 0.9300 |
C19—C20 | 1.371 (4) | C43—C42 | 1.380 (5) |
C19—C24 | 1.373 (4) | C43—H43 | 0.9300 |
C25—C26 | 1.377 (4) | C27—C28 | 1.361 (5) |
C25—C30 | 1.385 (4) | C27—H27 | 0.9300 |
C1—C6 | 1.373 (4) | C24—C23 | 1.383 (4) |
C1—C2 | 1.380 (4) | C24—H24 | 0.9300 |
C7—C8 | 1.382 (4) | C28—C29 | 1.372 (5) |
C7—C12 | 1.383 (4) | C28—H28 | 0.9300 |
C38—C43 | 1.370 (4) | C39—C40 | 1.382 (4) |
C38—C39 | 1.381 (4) | C39—H39 | 0.9300 |
C38—C37 | 1.479 (4) | C2—C3 | 1.380 (4) |
C8—C9 | 1.393 (4) | C2—H2 | 0.9300 |
C8—H8 | 0.9300 | C3—C4 | 1.355 (5) |
C14—C15 | 1.372 (4) | C3—H3 | 0.9300 |
C14—H14 | 0.9300 | C29—H29 | 0.9300 |
C26—C27 | 1.383 (4) | C23—H23 | 0.9300 |
C26—H26 | 0.9300 | C21—H21 | 0.9300 |
C18—C17 | 1.384 (4) | C4—C5 | 1.357 (5) |
C18—H18 | 0.9300 | C4—H4 | 0.9300 |
C36—C35 | 1.385 (4) | C10—C11 | 1.363 (5) |
C36—H36 | 0.9300 | C10—H10 | 0.9300 |
C15—C16 | 1.363 (4) | C41—C42 | 1.353 (5) |
C15—H15 | 0.9300 | C41—C40 | 1.357 (5) |
C32—C33 | 1.384 (4) | C41—H41 | 0.9300 |
C32—H32 | 0.9300 | C11—H11 | 0.9300 |
C9—C10 | 1.352 (5) | C5—H5 | 0.9300 |
C9—H9 | 0.9300 | C40—H40 | 0.9300 |
C30—C29 | 1.384 (4) | C42—H42 | 0.9300 |
P2—Ag1—P1 | 121.60 (2) | C34—C35—C36 | 120.6 (3) |
P2—Ag1—S1 | 108.40 (2) | C34—C35—H35 | 119.7 |
P1—Ag1—S1 | 113.89 (3) | C36—C35—H35 | 119.7 |
P2—Ag1—Br1 | 104.528 (18) | C19—C20—C21 | 121.3 (3) |
P1—Ag1—Br1 | 97.338 (18) | C19—C20—H20 | 119.3 |
S1—Ag1—Br1 | 109.550 (19) | C21—C20—H20 | 119.3 |
C31—P2—C19 | 102.34 (11) | C15—C16—C17 | 120.2 (3) |
C31—P2—C25 | 105.36 (12) | C15—C16—H16 | 119.9 |
C19—P2—C25 | 104.08 (11) | C17—C16—H16 | 119.9 |
C31—P2—Ag1 | 113.69 (8) | C33—C34—C35 | 119.4 (3) |
C19—P2—Ag1 | 117.29 (8) | C33—C34—H34 | 120.3 |
C25—P2—Ag1 | 112.76 (9) | C35—C34—H34 | 120.3 |
C1—P1—C7 | 105.53 (12) | C11—C12—C7 | 120.1 (3) |
C1—P1—C13 | 104.41 (12) | C11—C12—H12 | 119.9 |
C7—P1—C13 | 102.34 (11) | C7—C12—H12 | 119.9 |
C1—P1—Ag1 | 110.20 (8) | C21—C22—C23 | 119.5 (3) |
C7—P1—Ag1 | 116.31 (8) | C21—C22—H22 | 120.3 |
C13—P1—Ag1 | 116.78 (8) | C23—C22—H22 | 120.3 |
C37—S1—Ag1 | 109.90 (10) | C16—C17—C18 | 119.9 (3) |
C37—N1—H1A | 124 (2) | C16—C17—H17 | 120.1 |
C37—N1—H1B | 118 (2) | C18—C17—H17 | 120.1 |
H1A—N1—H1B | 117 (3) | C34—C33—C32 | 120.9 (3) |
C32—C31—C36 | 118.4 (2) | C34—C33—H33 | 119.5 |
C32—C31—P2 | 118.3 (2) | C32—C33—H33 | 119.5 |
C36—C31—P2 | 123.2 (2) | C38—C43—C42 | 121.3 (3) |
C18—C13—C14 | 118.7 (2) | C38—C43—H43 | 119.3 |
C18—C13—P1 | 118.69 (19) | C42—C43—H43 | 119.3 |
C14—C13—P1 | 122.6 (2) | C28—C27—C26 | 119.5 (3) |
C20—C19—C24 | 118.1 (2) | C28—C27—H27 | 120.2 |
C20—C19—P2 | 124.1 (2) | C26—C27—H27 | 120.2 |
C24—C19—P2 | 117.8 (2) | C19—C24—C23 | 120.3 (3) |
C26—C25—C30 | 118.1 (3) | C19—C24—H24 | 119.9 |
C26—C25—P2 | 124.8 (2) | C23—C24—H24 | 119.9 |
C30—C25—P2 | 117.1 (2) | C27—C28—C29 | 120.9 (3) |
C6—C1—C2 | 118.3 (3) | C27—C28—H28 | 119.6 |
C6—C1—P1 | 121.9 (2) | C29—C28—H28 | 119.6 |
C2—C1—P1 | 119.5 (2) | C38—C39—C40 | 120.5 (3) |
C8—C7—C12 | 118.5 (3) | C38—C39—H39 | 119.8 |
C8—C7—P1 | 125.1 (2) | C40—C39—H39 | 119.8 |
C12—C7—P1 | 116.3 (2) | C1—C2—C3 | 121.1 (3) |
C43—C38—C39 | 117.8 (3) | C1—C2—H2 | 119.5 |
C43—C38—C37 | 120.7 (3) | C3—C2—H2 | 119.5 |
C39—C38—C37 | 121.5 (3) | C4—C3—C2 | 119.8 (4) |
C7—C8—C9 | 120.2 (3) | C4—C3—H3 | 120.1 |
C7—C8—H8 | 119.9 | C2—C3—H3 | 120.1 |
C9—C8—H8 | 119.9 | C28—C29—C30 | 119.2 (3) |
C15—C14—C13 | 120.8 (3) | C28—C29—H29 | 120.4 |
C15—C14—H14 | 119.6 | C30—C29—H29 | 120.4 |
C13—C14—H14 | 119.6 | C22—C23—C24 | 120.8 (3) |
N1—C37—C38 | 117.5 (2) | C22—C23—H23 | 119.6 |
N1—C37—S1 | 121.9 (2) | C24—C23—H23 | 119.6 |
C38—C37—S1 | 120.6 (2) | C22—C21—C20 | 120.0 (3) |
C25—C26—C27 | 121.2 (3) | C22—C21—H21 | 120.0 |
C25—C26—H26 | 119.4 | C20—C21—H21 | 120.0 |
C27—C26—H26 | 119.4 | C3—C4—C5 | 120.4 (3) |
C13—C18—C17 | 120.3 (3) | C3—C4—H4 | 119.8 |
C13—C18—H18 | 119.9 | C5—C4—H4 | 119.8 |
C17—C18—H18 | 119.9 | C9—C10—C11 | 120.0 (3) |
C35—C36—C31 | 120.4 (3) | C9—C10—H10 | 120.0 |
C35—C36—H36 | 119.8 | C11—C10—H10 | 120.0 |
C31—C36—H36 | 119.8 | C42—C41—C40 | 120.1 (3) |
C16—C15—C14 | 120.0 (3) | C42—C41—H41 | 120.0 |
C16—C15—H15 | 120.0 | C40—C41—H41 | 120.0 |
C14—C15—H15 | 120.0 | C10—C11—C12 | 120.8 (3) |
C31—C32—C33 | 120.2 (3) | C10—C11—H11 | 119.6 |
C31—C32—H32 | 119.9 | C12—C11—H11 | 119.6 |
C33—C32—H32 | 119.9 | C4—C5—C6 | 120.3 (4) |
C10—C9—C8 | 120.3 (3) | C4—C5—H5 | 119.9 |
C10—C9—H9 | 119.8 | C6—C5—H5 | 119.9 |
C8—C9—H9 | 119.8 | C41—C40—C39 | 120.3 (3) |
C29—C30—C25 | 121.0 (3) | C41—C40—H40 | 119.8 |
C29—C30—H30 | 119.5 | C39—C40—H40 | 119.8 |
C25—C30—H30 | 119.5 | C41—C42—C43 | 119.9 (3) |
C1—C6—C5 | 120.2 (3) | C41—C42—H42 | 120.0 |
C1—C6—H6 | 119.9 | C43—C42—H42 | 120.0 |
C5—C6—H6 | 119.9 | ||
C19—P2—C31—C32 | −145.9 (2) | P1—C13—C18—C17 | −178.6 (2) |
C25—P2—C31—C32 | 105.5 (2) | C32—C31—C36—C35 | −2.1 (4) |
Ag1—P2—C31—C32 | −18.4 (2) | P2—C31—C36—C35 | 178.9 (2) |
C19—P2—C31—C36 | 33.1 (2) | C13—C14—C15—C16 | 0.8 (5) |
C25—P2—C31—C36 | −75.4 (2) | C36—C31—C32—C33 | 2.1 (4) |
Ag1—P2—C31—C36 | 160.6 (2) | P2—C31—C32—C33 | −178.9 (2) |
C1—P1—C13—C18 | 119.0 (2) | C7—C8—C9—C10 | −1.0 (4) |
C7—P1—C13—C18 | −131.2 (2) | C26—C25—C30—C29 | 1.2 (4) |
Ag1—P1—C13—C18 | −3.0 (3) | P2—C25—C30—C29 | −178.8 (2) |
C1—P1—C13—C14 | −60.7 (2) | C2—C1—C6—C5 | −1.8 (5) |
C7—P1—C13—C14 | 49.1 (2) | P1—C1—C6—C5 | −175.4 (3) |
Ag1—P1—C13—C14 | 177.32 (19) | C31—C36—C35—C34 | 0.7 (5) |
C31—P2—C19—C20 | −101.0 (3) | C24—C19—C20—C21 | −0.8 (5) |
C25—P2—C19—C20 | 8.6 (3) | P2—C19—C20—C21 | 179.1 (3) |
Ag1—P2—C19—C20 | 133.9 (2) | C14—C15—C16—C17 | −0.2 (5) |
C31—P2—C19—C24 | 78.9 (2) | C36—C35—C34—C33 | 0.6 (5) |
C25—P2—C19—C24 | −171.6 (2) | C8—C7—C12—C11 | 0.3 (5) |
Ag1—P2—C19—C24 | −46.3 (3) | P1—C7—C12—C11 | −178.6 (3) |
C31—P2—C25—C26 | 24.4 (3) | C15—C16—C17—C18 | 0.0 (5) |
C19—P2—C25—C26 | −82.9 (2) | C13—C18—C17—C16 | −0.5 (5) |
Ag1—P2—C25—C26 | 148.9 (2) | C35—C34—C33—C32 | −0.7 (5) |
C31—P2—C25—C30 | −155.6 (2) | C31—C32—C33—C34 | −0.7 (5) |
C19—P2—C25—C30 | 97.1 (2) | C39—C38—C43—C42 | 0.3 (6) |
Ag1—P2—C25—C30 | −31.0 (2) | C37—C38—C43—C42 | −179.7 (3) |
C7—P1—C1—C6 | −129.4 (2) | C25—C26—C27—C28 | 0.3 (5) |
C13—P1—C1—C6 | −21.9 (3) | C20—C19—C24—C23 | 0.6 (5) |
Ag1—P1—C1—C6 | 104.2 (2) | P2—C19—C24—C23 | −179.2 (3) |
C7—P1—C1—C2 | 57.0 (3) | C26—C27—C28—C29 | −0.7 (6) |
C13—P1—C1—C2 | 164.5 (2) | C43—C38—C39—C40 | −0.5 (5) |
Ag1—P1—C1—C2 | −69.4 (2) | C37—C38—C39—C40 | 179.5 (3) |
C1—P1—C7—C8 | 13.5 (3) | C6—C1—C2—C3 | 2.1 (5) |
C13—P1—C7—C8 | −95.4 (2) | P1—C1—C2—C3 | 175.9 (3) |
Ag1—P1—C7—C8 | 136.0 (2) | C1—C2—C3—C4 | −1.1 (5) |
C1—P1—C7—C12 | −167.7 (2) | C27—C28—C29—C30 | 1.3 (5) |
C13—P1—C7—C12 | 83.3 (2) | C25—C30—C29—C28 | −1.6 (5) |
Ag1—P1—C7—C12 | −45.2 (2) | C21—C22—C23—C24 | −0.6 (6) |
C12—C7—C8—C9 | 0.6 (4) | C19—C24—C23—C22 | 0.1 (6) |
P1—C7—C8—C9 | 179.4 (2) | C23—C22—C21—C20 | 0.5 (6) |
C18—C13—C14—C15 | −1.3 (4) | C19—C20—C21—C22 | 0.2 (6) |
P1—C13—C14—C15 | 178.4 (2) | C2—C3—C4—C5 | −0.3 (6) |
C43—C38—C37—N1 | −154.4 (3) | C8—C9—C10—C11 | 0.4 (5) |
C39—C38—C37—N1 | 25.6 (4) | C9—C10—C11—C12 | 0.6 (6) |
C43—C38—C37—S1 | 27.4 (4) | C7—C12—C11—C10 | −0.9 (6) |
C39—C38—C37—S1 | −152.6 (3) | C3—C4—C5—C6 | 0.6 (6) |
Ag1—S1—C37—N1 | 19.3 (3) | C1—C6—C5—C4 | 0.5 (6) |
Ag1—S1—C37—C38 | −162.44 (19) | C42—C41—C40—C39 | 0.6 (7) |
C30—C25—C26—C27 | −0.5 (4) | C38—C39—C40—C41 | 0.1 (6) |
P2—C25—C26—C27 | 179.5 (2) | C40—C41—C42—C43 | −0.8 (7) |
C14—C13—C18—C17 | 1.2 (4) | C38—C43—C42—C41 | 0.4 (7) |
Cg3 is the centroid of the C13–C18 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Br1i | 0.85 (1) | 2.54 (1) | 3.357 (3) | 161 (3) |
N1—H1B···Br1 | 0.85 (1) | 2.58 (1) | 3.413 (3) | 166 (3) |
C17—H17···Br1i | 0.93 | 2.91 | 3.789 (3) | 158 |
C22—H22···Cg3ii | 0.93 | 2.94 | 3.78 (3) | 151 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1/2, −y+3/2, z+1/2. |
Acknowledgements
We are grateful for financial support from the Center of Excellence for Innovation in Chemistry (PERCH–CIC), Office of the Higher Education Commission, Ministry of Education, the Department of Chemistry and the Graduate school, Prince of Songkla University.
References
Aslanidis, P., Karagiannidis, P., Akrivos, P. D., Krebs, B. & Läge, M. (1997). Inorg. Chim. Acta, 254, 277–284. CSD CrossRef CAS Web of Science Google Scholar
Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cox, P. J., Aslanidis, P., Karagiannidis, P. & Hadjikakou, S. (2000). Inorg. Chim. Acta, 310, 268–272. Web of Science CSD CrossRef CAS Google Scholar
Dennehy, M., Quinzani, O. V. & Jennings, M. (2007). J. Mol. Struct. 841, 110–117. Web of Science CSD CrossRef CAS Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Isab, A. A., Nawaz, S., Saleem, M., Altaf, M., Monim-ul-Mehboob, M., Ahmad, S. & Evans, H. S. (2010). Polyhedron, 29, 1251–1256. Web of Science CSD CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
McFarlane, W., Akrivos, P. D., Aslanidis, P., Karagiannidis, P., Hatzisymeon, C., Numan, M. & Kokkou, S. (1998). Inorg. Chim. Acta, 281, 121–125. Web of Science CSD CrossRef CAS Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
McKinnon, J. J., Spackman, M. A. & Mitchell, A. S. (2004). Acta Cryst. B60, 627–668. Web of Science CrossRef CAS IUCr Journals Google Scholar
Nawaz, S., Isab, A. A., Merz, K., Vasylyeva, V., Metzler-Nolte, N., Saleem, M. & Ahmad, S. (2011). Polyhedron, 30, 1502–1506. Web of Science CSD CrossRef CAS Google Scholar
Nomiya, K., Kasuga, N. C., Takamori, I. & Tsuda, K. (1998). Polyhedron, 17, 3519–3530. CSD CrossRef CAS Google Scholar
Ruangwut, W. & Pakawatchai, C. (2014). Acta Cryst. E70, m310–m311. CSD CrossRef IUCr Journals 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
Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19–32. Web of Science CrossRef CAS Google Scholar
Spackman, M. A. & McKinnon, J. J. (2002). CrystEngComm, 4, 378–392. Web of Science CrossRef CAS Google Scholar
Wattanakanjana, Y., Palamae, S., Ratthiwan, J. & Nimthong, R. (2014). Acta Cryst. E70, m61–m62. CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer. The University of Western Australia. Google Scholar
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