research communications
κS]bis(triphenylphosphane-κP)silver(I)
of chlorido[1-(4-nitrophenyl)thiourea-aDepartment of Chemistry, Boston University, Boston, Massachusetts 02215, University, and bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112 , Thailand
*Correspondence e-mail: yupa.t@psu.ac.th
In the title compound, [AgCl(C7H7N3O2S)(C18H15P)2], the AgI ion is in a distorted tetrahedral coordination environment formed by P atoms from two triphenylphosphane ligands, one terminal S atom from the 1-(4-nitrophenyl)thiourea ligand and a chloride ion. In the crystal, bifurcated (N—H)2⋯Cl hydrogen bonds [with graph-set motif R21(6)] connect complex molecules, forming zigzag chains along [001]. These chains are linked via weak C—H⋯O hydrogen bonds, forming a two-dimensional network parallel to (100). An intramolecular N—H⋯Cl hydrogen bond forming an S(6) ring is also observed.
Keywords: crystal structure; N—H⋯Cl hydrogen bonding; intramolecular hydrogen bonding; intermolecular hydrogen bonding.
CCDC reference: 1546767
1. Chemical context
Studies of thiourea and thiourea derivatives have recently attracted considerable attention because of their variety of biological properties such as increasing technologies for plasma membrane proteomics (Cordwell & Thingholm, 2010), antimicrobial and cytotoxic activity (Bielenica et al., 2015) and significant antifungal and anti-viral activity of curative rates (Wu et al., 2012). Silver(I) complexes containing triphenylphosphane as precursors have been studied extensively for the preparation of mixed ligands with thiourea derivatives (Mekarat et al., 2014; Wattanakanjana et al., 2014). Recently, we reported a complex that was prepared by reacting copper(I) chloride containing triphenylphosphane and 1-(4-nitrophenyl)thiourea ligands (Nimthong-Roldán et al., 2017). Herein, we report the of the compound formed using silver(I) instead of copper(I) under the same conditions, [AgCl(C7H7N3O2S)(C18H15P)2] (I).
2. Structural commentary
In compound (I), triphenylphosphane, PPh3, and a 1-(4-nitrophenyl)thiourea ligand, NPTU, as co-ligands coordinate the AgI ion with two P atoms from two PPh3 ligands, one terminal S atom from the NPTU ligand and one chloride ion, resulting in a distorted tetrahedral environment (Fig. 1). The Ag—S bond length of 2.6316 (5) is similar to that of 2.603 (4) Å found in [Ag2Cl2(CH5N3S)2(C18H15P)2], (Wattanakanjana et al., 2012). An intramolecular N2—H2B⋯Cl1 hydrogen bond with graph-set motif S(6) is observed (Table 1).
3. Supramolecular features
In the crystal, N2—H2A⋯Cl1 and N1—H1⋯Cl1 hydrogen bonds link the molecules, forming a zigzag chain along [001]. These chains are linked by weak C12—H12⋯O2 hydrogen bonds, leading to the formation of a two-dimensional network parallel to (100) (Fig. 2 and Table 1).
4. Database survey
A search of the Cambridge Structural Database (Version 5.37, Feb 2016 with two updates; Groom et al., 2016) revealed no complexes with the 1-(4-nitrophenyl)thiourea ligand, and only the of the ligand itself has been reported (LONSEN; Xian et al., 2008). A search for phenylthiourea ligands with substitutions on the phenyl ring yielded 34 hits. Of these, four hits were AgI complexes, namely TUYZAQ (Wattanakanjana et al., 2015), SUFDUU (Nimthong-Roldán et al., 2015b), WUFBIK (Nimthong-Roldán et al., 2015a), and XOFDED (Mekarat et al., 2014)
5. Synthesis and crystallization
Triphenylphosphane, PPh3 (0.16 g, 0.51 mmol) was dissolved in 30 ml of acetonitrile at 340 K and then silver(I) chloride, AgCl (0.04 g, 0.25 mmol) , was added. The mixture was stirred for 3 h and then 1-(4-nitrophenyl)-2- thiourea, NPTU (0.05 g, 0.25 mmol), was added. The resulting reaction mixture was heated under reflux for 3 h during which the precipitate gradually disappeared. The resulting clear solution was filtered and left to evaporate at room temperature. The crystalline complex, which deposited upon standing for a couple of days, was filtered off and dried in vacuo (0.16 g, 66% yield). M.p. 465–467 K. IR bands (KBr, cm−1): 3259 (w), 3134 (w), 3051(w), 2366 (w), 2345 (w), 1584 (w), 1509 (w), 1498 (w), 1458 (w), 1433 (w), 1399 (w), 1334 (s), 1297 (w), 1259 (w), 1181 (w), 1157 (w), 1110 (w), 1095 (w), 1027 (w), 998 (w), 890 (w), 851 (w), 746 (m), 720 (w), 694 (s), 670 (w), 594 (w), 515 (m), 501 (m), 491 (m).
6. Refinement
Crystal data, data collection and structure . All H atoms attached to carbon atoms and atom H1 attached to nitrogen atom N1 were positioned geometrically and constrained to ride on their parent atoms, with C—H = 0.95 Å and N1—H1 = 0.88 Å. The other nitrogen-bound H atoms were located in difference-Fourier maps and were refined with an N—H distance restraint of 0.88 (2) Å. Uiso(H) values were set to 1.2Ueq(C/N). Reflections 1 1 0, 1 1, 0 2 0, 1 2 0, 0 4 0, 2 1, 0 2 1, 0 1 1, 1 0 0, −5 11, 13 8 1, 6 15 10, 12 10 4, 15 13, 20 2, 0 22 11, 12 1 5, 23 11, 26 10, 4 9 12, 10 14 6, 20 9, 7 22 7, 8 5, 10 10 7, 0 5 14, 7 5 10, 8 4, 25 10, 20 12 and 14 9 were affected by the beam stop and were omitted from the refinement.
details are summarized in Table 2Supporting information
CCDC reference: 1546767
https://doi.org/10.1107/S2056989017006405/lh5841sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017006405/lh5841Isup2.hkl
Data collection: CrystalClear-SM Expert (Rigaku, 2014); cell
HKL-3000 (Otwinowski & Minor, 1997); data reduction: HKL-3000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).[AgCl(C7H7N3O2S)(C18H15P)2] | F(000) = 1768 |
Mr = 865.07 | Dx = 1.463 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 11.8581 (2) Å | Cell parameters from 73254 reflections |
b = 28.5087 (4) Å | θ = 6.0–72.3° |
c = 12.0272 (2) Å | µ = 6.33 mm−1 |
β = 104.9338 (17)° | T = 100 K |
V = 3928.57 (11) Å3 | Fragment, colourless |
Z = 4 | 0.25 × 0.23 × 0.18 mm |
Rigaku RAPID II curved image plate diffractometer | 7590 independent reflections |
Radiation source: microfocus X-ray tube | 7495 reflections with I > 2σ(I) |
Laterally graded multilayer (Goebel) mirror monochromator | Rint = 0.051 |
ω scans | θmax = 72.3°, θmin = 6.0° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −13→14 |
Tmin = 0.253, Tmax = 0.395 | k = −34→34 |
73254 measured reflections | l = −14→14 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0286P)2 + 4.5052P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
7590 reflections | Δρmax = 0.43 e Å−3 |
485 parameters | Δρmin = −0.37 e Å−3 |
2 restraints | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00032 (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. |
Refinement. NH2 hydrogen positions were refined with an N-H distance restraint of 0.88 (2) Angstrom. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.82775 (17) | 0.17354 (7) | 0.72805 (16) | 0.0133 (4) | |
C2 | 0.96312 (17) | 0.14219 (7) | 0.61654 (16) | 0.0139 (4) | |
C3 | 1.03535 (18) | 0.16067 (7) | 0.55233 (18) | 0.0165 (4) | |
H3 | 1.0332 | 0.1933 | 0.5361 | 0.020* | |
C4 | 1.10993 (18) | 0.13194 (7) | 0.51217 (18) | 0.0190 (4) | |
H4 | 1.1578 | 0.1444 | 0.4670 | 0.023* | |
C5 | 1.11381 (18) | 0.08464 (7) | 0.53871 (17) | 0.0174 (4) | |
C6 | 1.04603 (19) | 0.06567 (7) | 0.60585 (18) | 0.0194 (4) | |
H6 | 1.0514 | 0.0333 | 0.6249 | 0.023* | |
C7 | 0.97043 (19) | 0.09454 (7) | 0.64472 (18) | 0.0187 (4) | |
H7 | 0.9235 | 0.0819 | 0.6906 | 0.022* | |
C8 | 0.74747 (17) | 0.13044 (7) | 1.26846 (16) | 0.0138 (4) | |
C9 | 0.65144 (19) | 0.15917 (7) | 1.26283 (18) | 0.0179 (4) | |
H9 | 0.6270 | 0.1806 | 1.2007 | 0.022* | |
C10 | 0.5909 (2) | 0.15680 (7) | 1.3476 (2) | 0.0210 (5) | |
H10 | 0.5264 | 0.1770 | 1.3442 | 0.025* | |
C11 | 0.62485 (18) | 0.12492 (7) | 1.43677 (18) | 0.0189 (4) | |
H11 | 0.5831 | 0.1230 | 1.4943 | 0.023* | |
C12 | 0.71971 (18) | 0.09583 (7) | 1.44220 (17) | 0.0190 (4) | |
H12 | 0.7422 | 0.0737 | 1.5030 | 0.023* | |
C13 | 0.78211 (18) | 0.09879 (7) | 1.35929 (17) | 0.0166 (4) | |
H13 | 0.8482 | 0.0793 | 1.3644 | 0.020* | |
C14 | 0.93770 (17) | 0.17768 (6) | 1.20401 (16) | 0.0136 (4) | |
C15 | 0.93999 (18) | 0.20815 (7) | 1.29504 (17) | 0.0164 (4) | |
H15 | 0.8819 | 0.2059 | 1.3364 | 0.020* | |
C16 | 1.02734 (19) | 0.24204 (7) | 1.32554 (18) | 0.0205 (4) | |
H16 | 1.0283 | 0.2629 | 1.3873 | 0.025* | |
C17 | 1.11251 (19) | 0.24539 (7) | 1.26628 (19) | 0.0225 (5) | |
H17 | 1.1731 | 0.2680 | 1.2886 | 0.027* | |
C18 | 1.10938 (19) | 0.21572 (8) | 1.17397 (19) | 0.0235 (5) | |
H18 | 1.1675 | 0.2182 | 1.1326 | 0.028* | |
C19 | 1.02183 (18) | 0.18265 (8) | 1.14223 (18) | 0.0192 (4) | |
H19 | 1.0188 | 0.1631 | 1.0776 | 0.023* | |
C20 | 0.89340 (19) | 0.07855 (7) | 1.15416 (17) | 0.0181 (4) | |
C21 | 1.0099 (2) | 0.06968 (8) | 1.21129 (18) | 0.0233 (5) | |
H21 | 1.0565 | 0.0936 | 1.2558 | 0.028* | |
C22 | 1.0570 (3) | 0.02535 (9) | 1.2023 (2) | 0.0361 (6) | |
H22 | 1.1365 | 0.0193 | 1.2399 | 0.043* | |
C23 | 0.9895 (3) | −0.00974 (9) | 1.1395 (2) | 0.0416 (7) | |
H23 | 1.0225 | −0.0397 | 1.1336 | 0.050* | |
C24 | 0.8739 (3) | −0.00123 (8) | 1.0852 (2) | 0.0399 (7) | |
H24 | 0.8268 | −0.0256 | 1.0435 | 0.048* | |
C25 | 0.8263 (2) | 0.04271 (8) | 1.0911 (2) | 0.0294 (5) | |
H25 | 0.7472 | 0.0485 | 1.0518 | 0.035* | |
C26 | 0.40317 (17) | 0.12920 (7) | 0.91747 (17) | 0.0144 (4) | |
C27 | 0.43678 (19) | 0.11373 (8) | 1.03101 (18) | 0.0211 (4) | |
H27 | 0.5168 | 0.1076 | 1.0661 | 0.025* | |
C28 | 0.3548 (2) | 0.10713 (8) | 1.0934 (2) | 0.0258 (5) | |
H28 | 0.3784 | 0.0962 | 1.1705 | 0.031* | |
C29 | 0.2380 (2) | 0.11659 (8) | 1.0429 (2) | 0.0251 (5) | |
H29 | 0.1817 | 0.1122 | 1.0855 | 0.030* | |
C30 | 0.20359 (19) | 0.13244 (8) | 0.9305 (2) | 0.0236 (5) | |
H30 | 0.1237 | 0.1393 | 0.8966 | 0.028* | |
C31 | 0.28542 (18) | 0.13847 (7) | 0.86665 (19) | 0.0189 (4) | |
H31 | 0.2613 | 0.1488 | 0.7891 | 0.023* | |
C32 | 0.45452 (17) | 0.17405 (7) | 0.72094 (17) | 0.0145 (4) | |
C33 | 0.45617 (18) | 0.22199 (7) | 0.74552 (19) | 0.0190 (4) | |
H33 | 0.4862 | 0.2326 | 0.8224 | 0.023* | |
C34 | 0.41417 (19) | 0.25422 (7) | 0.6582 (2) | 0.0229 (5) | |
H34 | 0.4137 | 0.2867 | 0.6758 | 0.028* | |
C35 | 0.37279 (19) | 0.23917 (8) | 0.5452 (2) | 0.0237 (5) | |
H35 | 0.3453 | 0.2613 | 0.4853 | 0.028* | |
C36 | 0.37170 (19) | 0.19174 (8) | 0.52005 (19) | 0.0225 (4) | |
H36 | 0.3438 | 0.1814 | 0.4427 | 0.027* | |
C37 | 0.41126 (18) | 0.15910 (7) | 0.60767 (18) | 0.0178 (4) | |
H37 | 0.4087 | 0.1266 | 0.5901 | 0.021* | |
C38 | 0.51237 (17) | 0.07648 (7) | 0.77110 (17) | 0.0151 (4) | |
C39 | 0.4272 (2) | 0.04295 (8) | 0.7711 (2) | 0.0248 (5) | |
H39 | 0.3669 | 0.0495 | 0.8077 | 0.030* | |
C40 | 0.4301 (2) | −0.00014 (8) | 0.7180 (2) | 0.0308 (5) | |
H40 | 0.3719 | −0.0229 | 0.7187 | 0.037* | |
C41 | 0.5173 (2) | −0.01007 (7) | 0.66374 (19) | 0.0252 (5) | |
H41 | 0.5186 | −0.0395 | 0.6270 | 0.030* | |
C42 | 0.60271 (19) | 0.02319 (7) | 0.66335 (18) | 0.0212 (4) | |
H42 | 0.6624 | 0.0166 | 0.6259 | 0.025* | |
C43 | 0.60110 (19) | 0.06598 (7) | 0.71745 (18) | 0.0186 (4) | |
H43 | 0.6606 | 0.0884 | 0.7182 | 0.022* | |
N1 | 0.88013 (15) | 0.17306 (6) | 0.64028 (14) | 0.0148 (3) | |
H1 | 0.8585 | 0.1958 | 0.5899 | 0.018* | |
N2 | 0.74178 (15) | 0.20477 (6) | 0.71595 (15) | 0.0162 (3) | |
H2A | 0.727 (2) | 0.2227 (8) | 0.6547 (17) | 0.019* | |
H2B | 0.721 (2) | 0.2127 (8) | 0.7774 (17) | 0.019* | |
N3 | 1.18951 (16) | 0.05374 (6) | 0.49253 (16) | 0.0226 (4) | |
O1 | 1.25615 (14) | 0.07175 (6) | 0.44157 (15) | 0.0309 (4) | |
O2 | 1.18095 (15) | 0.01114 (6) | 0.50467 (15) | 0.0314 (4) | |
S1 | 0.86821 (4) | 0.13848 (2) | 0.84576 (4) | 0.01445 (10) | |
Cl1 | 0.73410 (4) | 0.24665 (2) | 0.97189 (4) | 0.01787 (10) | |
Ag1 | 0.70884 (2) | 0.15453 (2) | 0.95816 (2) | 0.01254 (6) | |
P1 | 0.51614 (4) | 0.13383 (2) | 0.83979 (4) | 0.01185 (10) | |
P2 | 0.82115 (4) | 0.13508 (2) | 1.15318 (4) | 0.01158 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0103 (9) | 0.0120 (9) | 0.0179 (9) | −0.0021 (7) | 0.0045 (7) | −0.0016 (7) |
C2 | 0.0143 (10) | 0.0136 (9) | 0.0140 (9) | 0.0017 (7) | 0.0042 (7) | −0.0015 (7) |
C3 | 0.0171 (11) | 0.0123 (9) | 0.0214 (10) | −0.0012 (7) | 0.0072 (8) | −0.0011 (7) |
C4 | 0.0163 (11) | 0.0192 (10) | 0.0233 (10) | −0.0021 (8) | 0.0082 (8) | −0.0030 (8) |
C5 | 0.0146 (10) | 0.0176 (10) | 0.0202 (10) | 0.0040 (8) | 0.0049 (8) | −0.0038 (8) |
C6 | 0.0235 (11) | 0.0126 (9) | 0.0230 (10) | 0.0048 (8) | 0.0076 (9) | 0.0022 (8) |
C7 | 0.0222 (11) | 0.0156 (10) | 0.0214 (10) | 0.0022 (8) | 0.0113 (8) | 0.0022 (8) |
C8 | 0.0136 (10) | 0.0127 (9) | 0.0157 (9) | −0.0030 (7) | 0.0047 (7) | −0.0008 (7) |
C9 | 0.0188 (11) | 0.0146 (10) | 0.0213 (10) | 0.0012 (8) | 0.0068 (8) | 0.0018 (8) |
C10 | 0.0192 (12) | 0.0178 (10) | 0.0293 (12) | 0.0029 (8) | 0.0118 (9) | −0.0001 (8) |
C11 | 0.0185 (11) | 0.0180 (10) | 0.0234 (10) | −0.0045 (8) | 0.0113 (8) | −0.0033 (8) |
C12 | 0.0207 (11) | 0.0178 (10) | 0.0192 (10) | −0.0020 (8) | 0.0064 (8) | 0.0031 (8) |
C13 | 0.0140 (10) | 0.0152 (9) | 0.0208 (10) | 0.0011 (7) | 0.0052 (8) | 0.0019 (8) |
C14 | 0.0120 (10) | 0.0103 (9) | 0.0179 (9) | 0.0008 (7) | 0.0028 (7) | 0.0028 (7) |
C15 | 0.0173 (10) | 0.0130 (9) | 0.0192 (10) | 0.0013 (7) | 0.0056 (8) | 0.0005 (7) |
C16 | 0.0251 (12) | 0.0116 (9) | 0.0219 (10) | −0.0014 (8) | 0.0009 (9) | −0.0014 (8) |
C17 | 0.0177 (11) | 0.0165 (10) | 0.0289 (11) | −0.0052 (8) | −0.0020 (9) | 0.0039 (8) |
C18 | 0.0150 (11) | 0.0290 (12) | 0.0278 (11) | −0.0047 (9) | 0.0077 (9) | 0.0037 (9) |
C19 | 0.0136 (10) | 0.0227 (11) | 0.0215 (10) | −0.0018 (8) | 0.0050 (8) | −0.0021 (8) |
C20 | 0.0256 (11) | 0.0145 (10) | 0.0177 (9) | 0.0016 (8) | 0.0116 (8) | 0.0019 (8) |
C21 | 0.0290 (12) | 0.0211 (11) | 0.0218 (10) | 0.0117 (9) | 0.0105 (9) | 0.0064 (8) |
C22 | 0.0482 (16) | 0.0373 (14) | 0.0283 (12) | 0.0303 (12) | 0.0197 (11) | 0.0134 (11) |
C23 | 0.085 (2) | 0.0183 (12) | 0.0312 (13) | 0.0258 (13) | 0.0327 (14) | 0.0094 (10) |
C24 | 0.076 (2) | 0.0108 (11) | 0.0357 (14) | 0.0014 (12) | 0.0192 (14) | −0.0020 (9) |
C25 | 0.0399 (15) | 0.0176 (11) | 0.0316 (12) | −0.0019 (10) | 0.0110 (11) | −0.0044 (9) |
C26 | 0.0130 (10) | 0.0102 (9) | 0.0215 (10) | −0.0009 (7) | 0.0072 (8) | −0.0034 (7) |
C27 | 0.0159 (11) | 0.0244 (11) | 0.0234 (10) | 0.0003 (8) | 0.0061 (8) | 0.0003 (8) |
C28 | 0.0268 (12) | 0.0283 (12) | 0.0262 (11) | −0.0029 (9) | 0.0137 (9) | 0.0009 (9) |
C29 | 0.0224 (12) | 0.0209 (11) | 0.0390 (13) | −0.0035 (9) | 0.0208 (10) | −0.0038 (9) |
C30 | 0.0125 (11) | 0.0210 (11) | 0.0400 (13) | −0.0005 (8) | 0.0115 (9) | −0.0033 (9) |
C31 | 0.0152 (10) | 0.0157 (10) | 0.0255 (10) | 0.0003 (8) | 0.0049 (8) | −0.0028 (8) |
C32 | 0.0082 (9) | 0.0146 (9) | 0.0218 (10) | −0.0002 (7) | 0.0056 (7) | 0.0013 (7) |
C33 | 0.0131 (10) | 0.0168 (10) | 0.0262 (10) | 0.0000 (8) | 0.0034 (8) | 0.0000 (8) |
C34 | 0.0152 (11) | 0.0150 (10) | 0.0380 (12) | 0.0000 (8) | 0.0059 (9) | 0.0027 (9) |
C35 | 0.0147 (11) | 0.0254 (11) | 0.0299 (11) | 0.0012 (8) | 0.0041 (9) | 0.0124 (9) |
C36 | 0.0159 (11) | 0.0321 (12) | 0.0201 (10) | −0.0002 (9) | 0.0054 (8) | 0.0043 (9) |
C37 | 0.0121 (10) | 0.0200 (10) | 0.0224 (10) | −0.0012 (7) | 0.0064 (8) | −0.0004 (8) |
C38 | 0.0147 (10) | 0.0120 (9) | 0.0177 (9) | 0.0017 (7) | 0.0027 (8) | 0.0005 (7) |
C39 | 0.0241 (12) | 0.0201 (11) | 0.0333 (12) | −0.0063 (9) | 0.0131 (10) | −0.0074 (9) |
C40 | 0.0374 (14) | 0.0161 (11) | 0.0423 (14) | −0.0132 (10) | 0.0165 (11) | −0.0091 (10) |
C41 | 0.0345 (13) | 0.0134 (10) | 0.0283 (11) | −0.0011 (9) | 0.0089 (10) | −0.0050 (8) |
C42 | 0.0228 (11) | 0.0169 (10) | 0.0252 (10) | 0.0034 (8) | 0.0088 (9) | −0.0027 (8) |
C43 | 0.0185 (11) | 0.0142 (10) | 0.0242 (10) | −0.0020 (8) | 0.0073 (8) | −0.0027 (8) |
N1 | 0.0176 (9) | 0.0113 (8) | 0.0181 (8) | 0.0044 (6) | 0.0091 (7) | 0.0038 (6) |
N2 | 0.0171 (9) | 0.0159 (8) | 0.0181 (8) | 0.0049 (6) | 0.0090 (7) | 0.0037 (7) |
N3 | 0.0205 (10) | 0.0211 (9) | 0.0262 (9) | 0.0052 (7) | 0.0063 (8) | −0.0058 (7) |
O1 | 0.0248 (9) | 0.0320 (9) | 0.0425 (10) | 0.0001 (7) | 0.0205 (8) | −0.0101 (7) |
O2 | 0.0366 (10) | 0.0196 (8) | 0.0410 (10) | 0.0112 (7) | 0.0158 (8) | −0.0010 (7) |
S1 | 0.0120 (2) | 0.0160 (2) | 0.0164 (2) | 0.00335 (17) | 0.00569 (17) | 0.00330 (17) |
Cl1 | 0.0236 (3) | 0.0121 (2) | 0.0184 (2) | −0.00173 (17) | 0.00615 (18) | −0.00192 (16) |
Ag1 | 0.00999 (9) | 0.01314 (8) | 0.01461 (8) | −0.00147 (4) | 0.00338 (6) | 0.00063 (5) |
P1 | 0.0085 (2) | 0.0110 (2) | 0.0165 (2) | −0.00051 (16) | 0.00401 (18) | −0.00144 (17) |
P2 | 0.0108 (2) | 0.0098 (2) | 0.0145 (2) | −0.00040 (17) | 0.00404 (18) | 0.00016 (17) |
C1—N2 | 1.333 (3) | C24—C25 | 1.384 (3) |
C1—N1 | 1.356 (2) | C24—H24 | 0.9500 |
C1—S1 | 1.698 (2) | C25—H25 | 0.9500 |
C2—C3 | 1.396 (3) | C26—C27 | 1.392 (3) |
C2—C7 | 1.397 (3) | C26—C31 | 1.398 (3) |
C2—N1 | 1.403 (2) | C26—P1 | 1.825 (2) |
C3—C4 | 1.381 (3) | C27—C28 | 1.386 (3) |
C3—H3 | 0.9500 | C27—H27 | 0.9500 |
C4—C5 | 1.384 (3) | C28—C29 | 1.387 (3) |
C4—H4 | 0.9500 | C28—H28 | 0.9500 |
C5—C6 | 1.388 (3) | C29—C30 | 1.384 (3) |
C5—N3 | 1.465 (3) | C29—H29 | 0.9500 |
C6—C7 | 1.384 (3) | C30—C31 | 1.394 (3) |
C6—H6 | 0.9500 | C30—H30 | 0.9500 |
C7—H7 | 0.9500 | C31—H31 | 0.9500 |
C8—C9 | 1.390 (3) | C32—C37 | 1.393 (3) |
C8—C13 | 1.395 (3) | C32—C33 | 1.398 (3) |
C8—P2 | 1.824 (2) | C32—P1 | 1.831 (2) |
C9—C10 | 1.391 (3) | C33—C34 | 1.388 (3) |
C9—H9 | 0.9500 | C33—H33 | 0.9500 |
C10—C11 | 1.385 (3) | C34—C35 | 1.389 (3) |
C10—H10 | 0.9500 | C34—H34 | 0.9500 |
C11—C12 | 1.385 (3) | C35—C36 | 1.385 (3) |
C11—H11 | 0.9500 | C35—H35 | 0.9500 |
C12—C13 | 1.389 (3) | C36—C37 | 1.393 (3) |
C12—H12 | 0.9500 | C36—H36 | 0.9500 |
C13—H13 | 0.9500 | C37—H37 | 0.9500 |
C14—C15 | 1.392 (3) | C38—C39 | 1.391 (3) |
C14—C19 | 1.396 (3) | C38—C43 | 1.401 (3) |
C14—P2 | 1.823 (2) | C38—P1 | 1.827 (2) |
C15—C16 | 1.395 (3) | C39—C40 | 1.389 (3) |
C15—H15 | 0.9500 | C39—H39 | 0.9500 |
C16—C17 | 1.381 (3) | C40—C41 | 1.387 (3) |
C16—H16 | 0.9500 | C40—H40 | 0.9500 |
C17—C18 | 1.389 (3) | C41—C42 | 1.388 (3) |
C17—H17 | 0.9500 | C41—H41 | 0.9500 |
C18—C19 | 1.381 (3) | C42—C43 | 1.385 (3) |
C18—H18 | 0.9500 | C42—H42 | 0.9500 |
C19—H19 | 0.9500 | C43—H43 | 0.9500 |
C20—C25 | 1.394 (3) | N1—H1 | 0.8800 |
C20—C21 | 1.398 (3) | N2—H2A | 0.877 (16) |
C20—P2 | 1.824 (2) | N2—H2B | 0.870 (16) |
C21—C22 | 1.397 (3) | N3—O1 | 1.230 (3) |
C21—H21 | 0.9500 | N3—O2 | 1.231 (2) |
C22—C23 | 1.379 (4) | S1—Ag1 | 2.6316 (5) |
C22—H22 | 0.9500 | Cl1—Ag1 | 2.6435 (5) |
C23—C24 | 1.379 (4) | Ag1—P1 | 2.4330 (5) |
C23—H23 | 0.9500 | Ag1—P2 | 2.4440 (5) |
N2—C1—N1 | 114.37 (17) | C28—C27—H27 | 119.6 |
N2—C1—S1 | 121.88 (15) | C26—C27—H27 | 119.6 |
N1—C1—S1 | 123.74 (15) | C27—C28—C29 | 119.8 (2) |
C3—C2—C7 | 119.50 (18) | C27—C28—H28 | 120.1 |
C3—C2—N1 | 116.00 (17) | C29—C28—H28 | 120.1 |
C7—C2—N1 | 124.28 (18) | C30—C29—C28 | 120.1 (2) |
C4—C3—C2 | 120.63 (19) | C30—C29—H29 | 120.0 |
C4—C3—H3 | 119.7 | C28—C29—H29 | 120.0 |
C2—C3—H3 | 119.7 | C29—C30—C31 | 120.4 (2) |
C3—C4—C5 | 118.92 (19) | C29—C30—H30 | 119.8 |
C3—C4—H4 | 120.5 | C31—C30—H30 | 119.8 |
C5—C4—H4 | 120.5 | C30—C31—C26 | 119.6 (2) |
C4—C5—C6 | 121.62 (19) | C30—C31—H31 | 120.2 |
C4—C5—N3 | 119.05 (19) | C26—C31—H31 | 120.2 |
C6—C5—N3 | 119.31 (18) | C37—C32—C33 | 119.18 (19) |
C7—C6—C5 | 119.18 (19) | C37—C32—P1 | 122.97 (15) |
C7—C6—H6 | 120.4 | C33—C32—P1 | 117.79 (15) |
C5—C6—H6 | 120.4 | C34—C33—C32 | 120.3 (2) |
C6—C7—C2 | 120.08 (19) | C34—C33—H33 | 119.8 |
C6—C7—H7 | 120.0 | C32—C33—H33 | 119.8 |
C2—C7—H7 | 120.0 | C33—C34—C35 | 120.2 (2) |
C9—C8—C13 | 119.44 (18) | C33—C34—H34 | 119.9 |
C9—C8—P2 | 117.84 (15) | C35—C34—H34 | 119.9 |
C13—C8—P2 | 122.70 (15) | C36—C35—C34 | 119.7 (2) |
C8—C9—C10 | 120.44 (19) | C36—C35—H35 | 120.1 |
C8—C9—H9 | 119.8 | C34—C35—H35 | 120.1 |
C10—C9—H9 | 119.8 | C35—C36—C37 | 120.3 (2) |
C11—C10—C9 | 119.8 (2) | C35—C36—H36 | 119.8 |
C11—C10—H10 | 120.1 | C37—C36—H36 | 119.8 |
C9—C10—H10 | 120.1 | C32—C37—C36 | 120.2 (2) |
C10—C11—C12 | 120.00 (19) | C32—C37—H37 | 119.9 |
C10—C11—H11 | 120.0 | C36—C37—H37 | 119.9 |
C12—C11—H11 | 120.0 | C39—C38—C43 | 118.99 (18) |
C11—C12—C13 | 120.40 (19) | C39—C38—P1 | 123.24 (16) |
C11—C12—H12 | 119.8 | C43—C38—P1 | 117.76 (15) |
C13—C12—H12 | 119.8 | C40—C39—C38 | 120.3 (2) |
C12—C13—C8 | 119.86 (19) | C40—C39—H39 | 119.9 |
C12—C13—H13 | 120.1 | C38—C39—H39 | 119.9 |
C8—C13—H13 | 120.1 | C41—C40—C39 | 120.4 (2) |
C15—C14—C19 | 118.90 (18) | C41—C40—H40 | 119.8 |
C15—C14—P2 | 122.60 (15) | C39—C40—H40 | 119.8 |
C19—C14—P2 | 118.24 (15) | C40—C41—C42 | 119.7 (2) |
C14—C15—C16 | 120.11 (19) | C40—C41—H41 | 120.2 |
C14—C15—H15 | 119.9 | C42—C41—H41 | 120.2 |
C16—C15—H15 | 119.9 | C43—C42—C41 | 120.1 (2) |
C17—C16—C15 | 120.3 (2) | C43—C42—H42 | 119.9 |
C17—C16—H16 | 119.9 | C41—C42—H42 | 119.9 |
C15—C16—H16 | 119.9 | C42—C43—C38 | 120.50 (19) |
C16—C17—C18 | 119.86 (19) | C42—C43—H43 | 119.7 |
C16—C17—H17 | 120.1 | C38—C43—H43 | 119.7 |
C18—C17—H17 | 120.1 | C1—N1—C2 | 130.59 (17) |
C19—C18—C17 | 120.0 (2) | C1—N1—H1 | 114.7 |
C19—C18—H18 | 120.0 | C2—N1—H1 | 114.7 |
C17—C18—H18 | 120.0 | C1—N2—H2A | 117.7 (16) |
C18—C19—C14 | 120.8 (2) | C1—N2—H2B | 117.4 (16) |
C18—C19—H19 | 119.6 | H2A—N2—H2B | 122 (2) |
C14—C19—H19 | 119.6 | O1—N3—O2 | 123.66 (18) |
C25—C20—C21 | 119.2 (2) | O1—N3—C5 | 118.22 (18) |
C25—C20—P2 | 116.29 (17) | O2—N3—C5 | 118.10 (18) |
C21—C20—P2 | 124.46 (17) | C1—S1—Ag1 | 103.88 (7) |
C22—C21—C20 | 119.3 (2) | P1—Ag1—P2 | 134.741 (17) |
C22—C21—H21 | 120.3 | P1—Ag1—S1 | 110.349 (16) |
C20—C21—H21 | 120.3 | P2—Ag1—S1 | 99.654 (16) |
C23—C22—C21 | 120.8 (3) | P1—Ag1—Cl1 | 110.591 (16) |
C23—C22—H22 | 119.6 | P2—Ag1—Cl1 | 98.075 (15) |
C21—C22—H22 | 119.6 | S1—Ag1—Cl1 | 96.894 (15) |
C22—C23—C24 | 119.8 (2) | C26—P1—C38 | 103.36 (9) |
C22—C23—H23 | 120.1 | C26—P1—C32 | 104.31 (9) |
C24—C23—H23 | 120.1 | C38—P1—C32 | 104.41 (9) |
C23—C24—C25 | 120.3 (3) | C26—P1—Ag1 | 114.88 (7) |
C23—C24—H24 | 119.9 | C38—P1—Ag1 | 113.04 (7) |
C25—C24—H24 | 119.9 | C32—P1—Ag1 | 115.51 (6) |
C24—C25—C20 | 120.5 (3) | C14—P2—C20 | 105.80 (9) |
C24—C25—H25 | 119.7 | C14—P2—C8 | 105.29 (9) |
C20—C25—H25 | 119.7 | C20—P2—C8 | 104.31 (9) |
C27—C26—C31 | 119.35 (19) | C14—P2—Ag1 | 110.44 (6) |
C27—C26—P1 | 117.57 (15) | C20—P2—Ag1 | 110.21 (7) |
C31—C26—P1 | 123.02 (16) | C8—P2—Ag1 | 119.78 (7) |
C28—C27—C26 | 120.7 (2) | ||
C7—C2—C3—C4 | 2.9 (3) | C38—C39—C40—C41 | −0.4 (4) |
N1—C2—C3—C4 | −171.96 (18) | C39—C40—C41—C42 | 0.4 (4) |
C2—C3—C4—C5 | −1.4 (3) | C40—C41—C42—C43 | 0.4 (3) |
C3—C4—C5—C6 | −1.0 (3) | C41—C42—C43—C38 | −1.2 (3) |
C3—C4—C5—N3 | 177.66 (18) | C39—C38—C43—C42 | 1.2 (3) |
C4—C5—C6—C7 | 1.7 (3) | P1—C38—C43—C42 | −179.65 (16) |
N3—C5—C6—C7 | −176.90 (19) | N2—C1—N1—C2 | −171.97 (19) |
C5—C6—C7—C2 | −0.1 (3) | S1—C1—N1—C2 | 9.2 (3) |
C3—C2—C7—C6 | −2.1 (3) | C3—C2—N1—C1 | −153.6 (2) |
N1—C2—C7—C6 | 172.30 (19) | C7—C2—N1—C1 | 31.8 (3) |
C13—C8—C9—C10 | 0.6 (3) | C4—C5—N3—O1 | 7.4 (3) |
P2—C8—C9—C10 | 179.24 (16) | C6—C5—N3—O1 | −173.91 (19) |
C8—C9—C10—C11 | −1.4 (3) | C4—C5—N3—O2 | −171.0 (2) |
C9—C10—C11—C12 | 0.7 (3) | C6—C5—N3—O2 | 7.7 (3) |
C10—C11—C12—C13 | 0.8 (3) | N2—C1—S1—Ag1 | 7.68 (17) |
C11—C12—C13—C8 | −1.5 (3) | N1—C1—S1—Ag1 | −173.58 (15) |
C9—C8—C13—C12 | 0.8 (3) | C27—C26—P1—C38 | 91.38 (17) |
P2—C8—C13—C12 | −177.71 (15) | C31—C26—P1—C38 | −85.81 (18) |
C19—C14—C15—C16 | −1.9 (3) | C27—C26—P1—C32 | −159.69 (16) |
P2—C14—C15—C16 | −175.92 (15) | C31—C26—P1—C32 | 23.13 (19) |
C14—C15—C16—C17 | −0.5 (3) | C27—C26—P1—Ag1 | −32.24 (18) |
C15—C16—C17—C18 | 1.7 (3) | C31—C26—P1—Ag1 | 150.58 (15) |
C16—C17—C18—C19 | −0.6 (3) | C39—C38—P1—C26 | 8.1 (2) |
C17—C18—C19—C14 | −1.8 (3) | C43—C38—P1—C26 | −170.92 (16) |
C15—C14—C19—C18 | 3.1 (3) | C39—C38—P1—C32 | −100.71 (19) |
P2—C14—C19—C18 | 177.33 (17) | C43—C38—P1—C32 | 80.22 (17) |
C25—C20—C21—C22 | 1.1 (3) | C39—C38—P1—Ag1 | 132.96 (17) |
P2—C20—C21—C22 | −177.62 (17) | C43—C38—P1—Ag1 | −46.11 (17) |
C20—C21—C22—C23 | −1.0 (3) | C37—C32—P1—C26 | −104.98 (18) |
C21—C22—C23—C24 | −0.3 (4) | C33—C32—P1—C26 | 77.84 (17) |
C22—C23—C24—C25 | 1.6 (4) | C37—C32—P1—C38 | 3.18 (19) |
C23—C24—C25—C20 | −1.6 (4) | C33—C32—P1—C38 | −174.00 (16) |
C21—C20—C25—C24 | 0.2 (3) | C37—C32—P1—Ag1 | 127.96 (16) |
P2—C20—C25—C24 | 179.03 (19) | C33—C32—P1—Ag1 | −49.22 (17) |
C31—C26—C27—C28 | 0.5 (3) | C15—C14—P2—C20 | −126.80 (16) |
P1—C26—C27—C28 | −176.77 (17) | C19—C14—P2—C20 | 59.16 (17) |
C26—C27—C28—C29 | −0.8 (3) | C15—C14—P2—C8 | −16.70 (18) |
C27—C28—C29—C30 | 0.2 (3) | C19—C14—P2—C8 | 169.26 (16) |
C28—C29—C30—C31 | 0.8 (3) | C15—C14—P2—Ag1 | 113.94 (15) |
C29—C30—C31—C26 | −1.1 (3) | C19—C14—P2—Ag1 | −60.09 (16) |
C27—C26—C31—C30 | 0.5 (3) | C25—C20—P2—C14 | −163.63 (17) |
P1—C26—C31—C30 | 177.59 (16) | C21—C20—P2—C14 | 15.1 (2) |
C37—C32—C33—C34 | 0.6 (3) | C25—C20—P2—C8 | 85.58 (18) |
P1—C32—C33—C34 | 177.89 (16) | C21—C20—P2—C8 | −95.71 (19) |
C32—C33—C34—C35 | −1.6 (3) | C25—C20—P2—Ag1 | −44.22 (18) |
C33—C34—C35—C36 | 1.1 (3) | C21—C20—P2—Ag1 | 134.49 (16) |
C34—C35—C36—C37 | 0.4 (3) | C9—C8—P2—C14 | 92.78 (17) |
C33—C32—C37—C36 | 0.9 (3) | C13—C8—P2—C14 | −88.67 (17) |
P1—C32—C37—C36 | −176.27 (16) | C9—C8—P2—C20 | −156.06 (16) |
C35—C36—C37—C32 | −1.4 (3) | C13—C8—P2—C20 | 22.50 (19) |
C43—C38—C39—C40 | −0.4 (3) | C9—C8—P2—Ag1 | −32.22 (18) |
P1—C38—C39—C40 | −179.50 (19) | C13—C8—P2—Ag1 | 146.34 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl1i | 0.88 | 2.41 | 3.2454 (17) | 159 |
N2—H2A···Cl1i | 0.88 (2) | 2.39 (2) | 3.2257 (18) | 160 (2) |
N2—H2B···Cl1 | 0.87 (2) | 2.50 (2) | 3.3247 (18) | 159 (2) |
C12—H12···O2ii | 0.95 | 2.60 | 3.272 (3) | 129 |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+2, −y, −z+2. |
Acknowledgements
Financial support from the Department of Chemistry, Faculty of Science, Prince of Songkla University, is gratefully acknowledged. We would like to thank Dr Matthias Zeller and Purdue University for assistance with the X-ray
and use of structure programs based on funding by the National Science Foundation of the United States (CHE-1625543).References
Bielenica, A., Stefańska, J., Stępień, K., Napiórkowska, A., Augustynowicz-Kopeć, E., Sanna, G., Madeddu, S., Boi, S., Giliberti, G., Wrzosek, M. & Struga, M. (2015). Eur. J. Med. Chem. 101, 111–125. Web of Science CrossRef CAS PubMed Google Scholar
Cordwell, S. C. & Thingholm, T. E. (2010). Proteomics, 10, 611–627. Web of Science CrossRef PubMed CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hübschle, C. B., Sheldrick, G. M. & Dittrich, B. (2011). J. Appl. Cryst. 44, 1281–1284. Web of Science CrossRef IUCr Journals 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
Mekarat, S., Pakawatchai, C. & Saithong, S. (2014). Acta Cryst. E70, m281–m282. CSD CrossRef IUCr Journals Google Scholar
Nimthong-Roldán, A., Promsuwhan, N., Puetpaiboon, W. & Wattanakanjana, Y. (2017). Acta Cryst. E73, 41–44. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nimthong-Roldán, A., Ratthiwal, J. & Wattanakanjana, Y. (2015a). Acta Cryst. E71, m133–m134. Web of Science CSD CrossRef IUCr Journals Google Scholar
Nimthong-Roldán, A., Wattanakanjana, Y. & Rodkeaw, J. (2015b). Acta Cryst. E71, m89–m90. Web of Science CSD CrossRef IUCr Journals Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rigaku (2014). CrystalClear-SM Expert. Rigaku Corporation, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wattanakanjana, Y., Nimthong, A. & Darasuriyong, C. (2014). Acta Cryst. E70, m337–m338. CSD CrossRef IUCr Journals Google Scholar
Wattanakanjana, Y., Nimthong-Roldán, A., Palavat, S. & Puetpaiboon, W. (2015). Acta Cryst. E71, m187–m188. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wattanakanjana, Y., Pakawatchai, C., Kowittheeraphong, S. & Nimthong, R. (2012). Acta Cryst. E68, m1572–m1573. 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
Wu, J., Shi, Q., Chen, Z., He, M., Jin, L. & Hu, D. (2012). Molecules, 17, 5139–5150. Web of Science CrossRef CAS PubMed Google Scholar
Xian, L., Wang, Y. & Zhang, B. (2008). Z. Kristallogr. New Cryst. Struct. 223, 411–412. CAS Google Scholar
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