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

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ISSN: 2414-3146

Bis[(4-methyl­phen­yl)di­phenyl­phosphine-κP](nitrito-κ2O,O′)silver(I)

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aDepartment of Chemical Sciences, University of Johannesburg, PO Box 524, Auckland Park, 2006, Johannesburg, South Africa, and bDepartment of Chemistry, University of Pretoria, Lynnwood Road, Hatfield, Pretoria, 0002, South Africa
*Correspondence e-mail: rmeijboom@uj.ac.za

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 29 July 2022; accepted 1 August 2022; online 12 August 2022)

The title AgI complex, [Ag(NO2)(C19H17P)2], reveals a distorted pseudo-trigonal–planar shape around the AgI atom geometry resulting from the coordination of two phosphine ligands, as well as a nitrito-O,O′ ligand coordinating to the silver(I) atom through the oxygen atoms; in this description, the two oxygen atoms are assumed to occupy one position, forming an acute O—Ag—O angle of 51.44 (9)°. The plane resulting from the NO2 coordination to Ag is nearly perpendicular to the plane from the coordination of the phosphine-P atoms to Ag [dihedral angle = 86.43 (9)°].

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

Structure description

The mol­ecular structure of the title compound is shown in Fig. 1[link]. The complex crystallizes in the monoclinic space group P21/c with Z = 4. The asymmetric unit contains one complete silver complex mol­ecule, featuring an AgI atom, two diphenyl-p-tolyl­phosphine ligands, and one NO2 coordinating in a bidentate fashion. Near-identical Ag—P bond lengths are observed [Ag1—P1 = 2.4209 (7) Å and Ag1—P2 = 2.4251 (8) Å]. The nitrito ligand is similarly coordinating in a near symmetric fashion (Ag1—O1 = 2.422 (2), Ag1—O2 = 2.415 (2), N1—O1 = 1.253 (4) and N1–O2 = 1.255 (4) Å). As seen in Fig. 1[link], the four-coordinate silver(I) atom essentially exhibits a pseudo trigonal–planar shape with the three coordinating ligands, with bond angles P1—Ag1—P2 [129.51 (3)°], P1—Ag1—O1 [116.23 (7)°], P1—Ag1—O2 [111.09 (7)°], P2—Ag1—O1 [110.79 (7)°], P2—Ag1—O2 [111.96 (7)°], and O1—Ag1—O2 [51.44 (9)°]; in this description, the two oxygen atoms are assumed to occupy one position. The plane Pl1 defined by Ag1, O1, O2 and N1 crosses the plane Pl2 defined by P1, P2 and Ag1 at an angle of 86.43 (9)°. The ipso-carbon atoms of each of the phosphine ligands overlap in a near-eclipsed fashion when viewed down the P1—Ag1—P2 plane Pl2. Corresponding torsion angles are Ag1—P1—C1—C2 = −23.4 (3)°, Ag1—P1—C7—C8 = −51.9 (3)°, Ag1—P1—C13—C14 = 147.8 (3)°, Ag1—P2—C20—C21 = −29.0 (3)°, Ag1—P2—C26—C27 = 133.3 (3) and Ag1—P2—C32—C33 = 132.3 (3)°. The complex packs in three dimensions as layers of mol­ecules, leaving thin corrugated channels in between the inorganic layers when viewed along the a axis (Fig. 2[link]).

[Figure 1]
Figure 1
Perspective view of the mol­ecular structure of the title compound showing displacement ellipsoids at the 50% probability level. Hydrogen atoms are omitted for clarity.
[Figure 2]
Figure 2
Packing diagrams as viewed along the (a) a and (b) c axes. Hydrogen atoms are omitted for clarity.

Synthesis and crystallization

Diphenyl-p-tolyl­phosphine (1 mmol) was dissolved in aceto­nitrile (10 ml). Silver nitrite (1 mmol) was dissolved in aceto­nitrile (5 ml). The diphenyl-p-tolyl­phosphine solution (10 ml) was added to the silver nitrite solution (5 ml), to give a 2:1 molar ratio reaction. The mixture was heated under reflux for 2 h after which the solution was left to crystallize.

Refinement

For full experimental details including crystal data, data collection and structure refinement details, refer to Table 1[link].

Table 1
Experimental details

Crystal data
Chemical formula [Ag(NO2)(C19H17P)2]
Mr 706.47
Crystal system, space group Monoclinic, P21/c
Temperature (K) 150
a, b, c (Å) 11.8709 (2), 18.6292 (2), 15.4003 (2)
β (°) 103.055 (1)
V3) 3317.68 (8)
Z 4
Radiation type Cu Kα
μ (mm−1) 6.05
Crystal size (mm) 0.24 × 0.13 × 0.10
 
Data collection
Diffractometer XtaLAB Synergy R, DW system, HyPix
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2022[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.188, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 41716, 7030, 6535
Rint 0.049
(sin θ/λ)max−1) 0.637
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.104, 1.07
No. of reflections 7030
No. of parameters 399
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.68, −0.82
Computer programs: CrysAlis PRO (Rigaku OD, 2022[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXT (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), SHELXL (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), and OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]).

Structural data


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: ShelXT (Sheldrick, 2015b); program(s) used to refine structure: SHELXL (Sheldrick, 2015a); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Bis[(4-methylphenyl)diphenylphosphine-κP](nitrito-κ2O,O')silver(I) top
Crystal data top
[Ag(NO2)(C19H17P)2]F(000) = 1448
Mr = 706.47Dx = 1.414 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
a = 11.8709 (2) ÅCell parameters from 29792 reflections
b = 18.6292 (2) Åθ = 3.8–78.9°
c = 15.4003 (2) ŵ = 6.05 mm1
β = 103.055 (1)°T = 150 K
V = 3317.68 (8) Å3Block, colourless
Z = 40.24 × 0.13 × 0.10 mm
Data collection top
XtaLAB Synergy R, DW system, HyPix
diffractometer
7030 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source6535 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.049
Detector resolution: 10.0000 pixels mm-1θmax = 79.2°, θmin = 3.8°
ω scansh = 1415
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2022)
k = 2323
Tmin = 0.188, Tmax = 1.000l = 1819
41716 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0425P)2 + 5.6399P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.002
7030 reflectionsΔρmax = 0.68 e Å3
399 parametersΔρmin = 0.82 e Å3
0 restraints
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.33615 (2)0.79867 (2)0.56752 (2)0.03178 (8)
P10.52794 (6)0.74875 (4)0.61894 (5)0.02991 (16)
P20.14991 (6)0.73885 (4)0.53633 (6)0.03298 (17)
O10.3244 (2)0.91204 (13)0.48903 (17)0.0459 (6)
O20.3250 (2)0.91839 (14)0.62523 (18)0.0506 (6)
N10.3202 (3)0.95191 (15)0.5538 (2)0.0492 (8)
C70.5331 (3)0.69367 (17)0.7177 (2)0.0325 (6)
C10.6466 (3)0.81224 (16)0.6530 (2)0.0321 (6)
C250.0805 (3)0.77034 (18)0.4467 (2)0.0380 (7)
H250.08570.72240.42530.046*
C200.0223 (3)0.79524 (16)0.5000 (2)0.0334 (6)
C260.1234 (3)0.69196 (16)0.6342 (2)0.0355 (7)
C130.5720 (3)0.68644 (16)0.5419 (2)0.0337 (6)
C60.7500 (3)0.79432 (18)0.7117 (2)0.0385 (7)
H60.76100.74730.73600.046*
C240.1757 (3)0.8154 (2)0.4248 (2)0.0443 (8)
H240.24620.79800.38880.053*
C320.1398 (3)0.66934 (17)0.4515 (2)0.0360 (7)
C20.6317 (3)0.88145 (17)0.6186 (2)0.0352 (7)
H20.56100.89430.57900.042*
C80.4942 (3)0.7238 (2)0.7887 (2)0.0413 (7)
H80.47260.77290.78700.050*
C370.1822 (3)0.68542 (19)0.3764 (2)0.0425 (8)
H370.20950.73250.36900.051*
C310.2138 (3)0.65361 (19)0.6870 (3)0.0456 (8)
H310.28590.65100.67020.055*
C50.8371 (3)0.8450 (2)0.7349 (3)0.0461 (8)
H50.90760.83260.77500.055*
C180.4881 (3)0.64259 (19)0.4912 (3)0.0440 (8)
H180.40960.64850.49410.053*
C100.5184 (3)0.6103 (2)0.8646 (2)0.0459 (8)
H100.51190.58160.91430.055*
C120.5662 (3)0.62220 (17)0.7224 (2)0.0374 (7)
H120.59420.60140.67500.045*
C140.6851 (3)0.6784 (2)0.5339 (3)0.0474 (8)
H140.74370.70890.56650.057*
C110.5589 (3)0.5806 (2)0.7959 (2)0.0447 (8)
H110.58190.53170.79850.054*
C40.8218 (3)0.9132 (2)0.7003 (2)0.0453 (8)
H40.88170.94780.71670.054*
C30.7192 (3)0.93168 (19)0.6415 (2)0.0445 (8)
H30.70900.97870.61710.053*
C230.1685 (3)0.8854 (2)0.4552 (3)0.0457 (8)
H230.23350.91640.43980.055*
C210.0295 (3)0.86579 (18)0.5299 (3)0.0447 (8)
H210.10000.88370.56530.054*
C270.0206 (3)0.6970 (2)0.6615 (3)0.0491 (9)
H270.04220.72350.62710.059*
C290.0976 (4)0.6233 (2)0.7899 (3)0.0515 (9)
H290.08780.59920.84210.062*
C350.1463 (3)0.5644 (2)0.3217 (3)0.0482 (8)
C90.4873 (3)0.6817 (2)0.8616 (2)0.0492 (9)
H90.46090.70230.90980.059*
C220.0663 (3)0.9098 (2)0.5080 (3)0.0518 (9)
H220.06150.95770.52970.062*
C360.1850 (3)0.6340 (2)0.3126 (3)0.0465 (8)
H360.21370.64620.26170.056*
C300.2004 (3)0.6192 (2)0.7633 (3)0.0520 (9)
H300.26280.59240.79780.062*
C170.5172 (4)0.5902 (2)0.4363 (3)0.0523 (9)
H170.45850.56010.40280.063*
C330.0991 (3)0.60034 (19)0.4599 (3)0.0488 (9)
H330.06890.58820.51010.059*
C150.7132 (4)0.6261 (2)0.4787 (3)0.0580 (11)
H150.79140.62100.47440.070*
C160.6305 (4)0.5809 (2)0.4296 (3)0.0542 (10)
C280.0095 (4)0.6631 (2)0.7393 (3)0.0579 (10)
H280.06110.66760.75810.069*
C340.1023 (4)0.5492 (2)0.3954 (3)0.0568 (10)
H340.07350.50250.40190.068*
C380.1539 (4)0.5072 (3)0.2557 (3)0.0684 (12)
H38A0.08150.50560.21000.103*
H38B0.16680.46070.28600.103*
H38C0.21830.51770.22750.103*
C190.6634 (5)0.5233 (3)0.3706 (4)0.0806 (16)
H19A0.64000.47630.38890.121*
H19B0.74730.52390.37630.121*
H19C0.62420.53250.30850.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02537 (12)0.02500 (12)0.04510 (14)0.00004 (7)0.00826 (9)0.00223 (8)
P10.0263 (3)0.0251 (3)0.0388 (4)0.0012 (3)0.0084 (3)0.0051 (3)
P20.0250 (3)0.0251 (4)0.0489 (5)0.0007 (3)0.0084 (3)0.0014 (3)
O10.0571 (15)0.0328 (12)0.0506 (14)0.0036 (11)0.0179 (12)0.0019 (10)
O20.0616 (16)0.0403 (14)0.0527 (15)0.0017 (12)0.0191 (12)0.0120 (12)
N10.0524 (18)0.0248 (14)0.071 (2)0.0032 (12)0.0154 (15)0.0042 (14)
C70.0261 (14)0.0343 (16)0.0376 (16)0.0021 (11)0.0080 (12)0.0028 (12)
C10.0288 (14)0.0299 (15)0.0390 (16)0.0013 (12)0.0104 (12)0.0028 (12)
C250.0315 (16)0.0320 (16)0.0496 (19)0.0001 (12)0.0075 (13)0.0020 (14)
C200.0252 (14)0.0295 (15)0.0462 (17)0.0008 (11)0.0098 (12)0.0019 (12)
C260.0319 (15)0.0267 (14)0.0482 (18)0.0009 (12)0.0097 (13)0.0024 (13)
C130.0364 (16)0.0284 (14)0.0373 (16)0.0020 (12)0.0105 (13)0.0086 (12)
C60.0302 (16)0.0354 (17)0.0488 (19)0.0031 (12)0.0064 (13)0.0082 (14)
C240.0332 (17)0.051 (2)0.0455 (19)0.0061 (15)0.0027 (14)0.0003 (16)
C320.0291 (15)0.0294 (15)0.0499 (18)0.0013 (12)0.0094 (13)0.0004 (13)
C20.0336 (16)0.0323 (15)0.0381 (16)0.0010 (12)0.0049 (12)0.0034 (12)
C80.0414 (18)0.0389 (17)0.0440 (18)0.0020 (14)0.0107 (14)0.0029 (14)
C370.0407 (18)0.0345 (17)0.052 (2)0.0064 (14)0.0102 (15)0.0017 (15)
C310.0332 (17)0.0369 (17)0.068 (2)0.0016 (14)0.0136 (16)0.0122 (16)
C50.0319 (16)0.053 (2)0.051 (2)0.0049 (15)0.0037 (14)0.0041 (16)
C180.0378 (18)0.0388 (18)0.056 (2)0.0015 (14)0.0121 (15)0.0036 (15)
C100.0444 (19)0.054 (2)0.0378 (18)0.0127 (16)0.0067 (14)0.0094 (15)
C120.0369 (16)0.0339 (16)0.0428 (17)0.0064 (13)0.0119 (13)0.0091 (13)
C140.0400 (19)0.046 (2)0.063 (2)0.0086 (15)0.0252 (17)0.0084 (17)
C110.0467 (19)0.0419 (19)0.0436 (19)0.0007 (15)0.0064 (15)0.0128 (15)
C40.0398 (18)0.0428 (19)0.053 (2)0.0134 (15)0.0101 (15)0.0008 (16)
C30.0465 (19)0.0351 (17)0.050 (2)0.0054 (14)0.0082 (15)0.0064 (15)
C230.0373 (18)0.0406 (18)0.059 (2)0.0137 (14)0.0114 (15)0.0070 (16)
C210.0310 (16)0.0308 (16)0.071 (2)0.0017 (13)0.0083 (15)0.0048 (15)
C270.0391 (19)0.050 (2)0.062 (2)0.0066 (16)0.0194 (17)0.0084 (17)
C290.068 (3)0.0368 (18)0.054 (2)0.0029 (17)0.0217 (19)0.0043 (16)
C350.0433 (19)0.0421 (19)0.061 (2)0.0021 (15)0.0152 (17)0.0068 (17)
C90.049 (2)0.064 (2)0.0366 (18)0.0079 (18)0.0137 (15)0.0050 (16)
C220.044 (2)0.0314 (17)0.081 (3)0.0053 (15)0.0172 (19)0.0036 (17)
C360.0430 (19)0.052 (2)0.048 (2)0.0034 (16)0.0178 (16)0.0013 (16)
C300.047 (2)0.0399 (19)0.067 (2)0.0023 (16)0.0076 (18)0.0153 (17)
C170.056 (2)0.046 (2)0.057 (2)0.0090 (17)0.0154 (18)0.0139 (17)
C330.058 (2)0.0320 (17)0.062 (2)0.0083 (16)0.0264 (18)0.0040 (16)
C150.052 (2)0.056 (2)0.078 (3)0.0100 (19)0.040 (2)0.016 (2)
C160.069 (3)0.044 (2)0.059 (2)0.0045 (19)0.033 (2)0.0089 (17)
C280.057 (2)0.056 (2)0.071 (3)0.0122 (19)0.036 (2)0.012 (2)
C340.069 (3)0.0321 (18)0.076 (3)0.0061 (17)0.032 (2)0.0040 (18)
C380.071 (3)0.065 (3)0.076 (3)0.001 (2)0.030 (2)0.014 (2)
C190.094 (4)0.072 (3)0.090 (4)0.013 (3)0.051 (3)0.037 (3)
Geometric parameters (Å, º) top
Ag1—P12.4209 (7)C32—C371.395 (5)
Ag1—P22.4251 (8)C32—C331.390 (5)
Ag1—O12.422 (2)C2—C31.383 (5)
Ag1—O22.415 (2)C8—C91.386 (5)
P1—C71.825 (3)C37—C361.377 (5)
P1—C11.823 (3)C31—C301.380 (5)
P1—C131.820 (3)C5—C41.373 (5)
P2—C201.824 (3)C18—C171.385 (5)
P2—C261.830 (3)C10—C111.373 (5)
P2—C321.824 (3)C10—C91.380 (6)
O1—N11.253 (4)C12—C111.389 (5)
O2—N11.255 (4)C14—C151.382 (5)
C7—C81.396 (5)C4—C31.387 (5)
C7—C121.386 (4)C23—C221.377 (5)
C1—C61.391 (4)C21—C221.380 (5)
C1—C21.390 (4)C27—C281.386 (6)
C25—C201.388 (4)C29—C301.374 (6)
C25—C241.387 (5)C29—C281.374 (6)
C20—C211.389 (4)C35—C361.394 (5)
C26—C311.388 (5)C35—C341.381 (6)
C26—C271.381 (5)C35—C381.489 (6)
C13—C181.384 (5)C17—C161.383 (6)
C13—C141.384 (5)C33—C341.383 (5)
C6—C51.386 (5)C15—C161.381 (6)
C24—C231.381 (5)C16—C191.513 (6)
P1—Ag1—P2129.51 (3)C5—C6—C1120.1 (3)
P1—Ag1—O1116.23 (7)C23—C24—C25120.3 (3)
O1—Ag1—P2110.79 (7)C37—C32—P2117.7 (2)
O2—Ag1—P1111.09 (7)C33—C32—P2123.9 (3)
O2—Ag1—P2111.96 (7)C33—C32—C37118.3 (3)
O2—Ag1—O151.44 (9)C3—C2—C1120.4 (3)
C7—P1—Ag1109.92 (10)C9—C8—C7119.8 (3)
C1—P1—Ag1116.95 (10)C36—C37—C32120.9 (3)
C1—P1—C7104.28 (14)C30—C31—C26121.0 (3)
C13—P1—Ag1114.79 (11)C4—C5—C6120.3 (3)
C13—P1—C7103.00 (14)C13—C18—C17120.9 (3)
C13—P1—C1106.52 (14)C11—C10—C9119.9 (3)
C20—P2—Ag1116.91 (10)C7—C12—C11120.6 (3)
C20—P2—C26104.02 (15)C15—C14—C13120.3 (4)
C26—P2—Ag1112.02 (11)C10—C11—C12120.1 (3)
C32—P2—Ag1112.17 (10)C5—C4—C3120.2 (3)
C32—P2—C20105.88 (15)C2—C3—C4119.8 (3)
C32—P2—C26104.80 (15)C22—C23—C24119.4 (3)
N1—O1—Ag197.3 (2)C22—C21—C20119.8 (3)
N1—O2—Ag197.59 (19)C26—C27—C28119.7 (4)
O1—N1—O2113.6 (3)C28—C29—C30118.3 (4)
C8—C7—P1118.2 (2)C36—C35—C38121.7 (4)
C12—C7—P1122.7 (3)C34—C35—C36117.8 (3)
C12—C7—C8119.0 (3)C34—C35—C38120.5 (4)
C6—C1—P1122.8 (2)C10—C9—C8120.6 (3)
C2—C1—P1117.9 (2)C23—C22—C21121.0 (3)
C2—C1—C6119.2 (3)C37—C36—C35121.0 (3)
C24—C25—C20120.1 (3)C29—C30—C31120.6 (4)
C25—C20—P2123.2 (2)C16—C17—C18121.0 (4)
C25—C20—C21119.4 (3)C34—C33—C32120.2 (4)
C21—C20—P2117.3 (2)C16—C15—C14121.7 (4)
C31—C26—P2118.3 (3)C17—C16—C19121.4 (4)
C27—C26—P2123.1 (3)C15—C16—C17117.8 (4)
C27—C26—C31118.4 (3)C15—C16—C19120.8 (4)
C18—C13—P1117.9 (3)C29—C28—C27121.8 (4)
C14—C13—P1123.7 (3)C35—C34—C33121.8 (4)
C14—C13—C18118.3 (3)
 

Acknowledgements

We would like to greatly acknowledge the National Research Foundation (NRF, SA), University of Pretoria and the University of Johannesburg for funding provided.

Funding information

Funding for this research was provided by: National Research Foundation (grant No. 138280).

References

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First citationRigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.  Google Scholar
First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar

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