Literature DB >> 22412470

Chlorido[2-({[2-(diphenyl-phosphan-yl)-benzyl-idene]amino}-meth-yl)thio-phene-κN,P]methyl-palladium(II).

William M Motswainyana, Martin O Onani, Roger A Lalancette.   

Abstract

In the title compound, [Pd(CH(3))Cl(C(24)H(20)NPS)], the Pd(II) ion is coordinated in a distorted square-planar environment which includes the P and N atoms of the bis-chelating ligand. The thio-phene ring is rotationally ordered, unlike in the majority of crystal structures containing this group.

Entities:  

Year:  2012        PMID： 22412470      PMCID： PMC3297280          DOI： 10.1107/S1600536812007295

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of pan class="Chemical">imino-phosphine ligands and their transition pan class="Chemical">metal-based complexes, see: Nobre & Monteiro (2009 ▶); Pelagatti et al. (2005 ▶); Reddy et al. (2001 ▶); Espinet & Soulantica (1999 ▶). For related structures, see: Onani et al. (2010 ▶); Vaughan et al. (2011 ▶).

Experimental

Crystal data

[pan class="Chemical">Pd(CH3)Cl(pan class="Chemical">C24H20NPS)] M = 542.32 Monopan class="Chemical">clinipan class="Chemical">c, a = 24.6534 (4) Å b = 10.0118 (1) Å pan class="Chemical">c = 18.4507 (3) Å β = 98.027 (1)° V = 4509.47 (11) Å3 Z = 8 pan class="Chemical">Cu Kα radiation μ = 9.35 mm−1 T = 100 K 0.26 × 0.15 × 0.08 mm

Data collection

Bruker SMART pan class="Chemical">Cpan class="Chemical">CD APEXII diffractometer Absorption pan class="Chemical">correction: numerical (SADABS; Sheldrick, 2008a ▶) T min = 0.195, T max = 0.522 22554 measured reflepan class="Chemical">ctions 4048 independent reflepan class="Chemical">ctions 3919 reflepan class="Chemical">ctions with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.024 wR(F 2) = 0.062 S = 1.11 4048 reflepan class="Chemical">ctions 272 parameters H-atom parameters pan class="Chemical">constrained Δρmax = 0.50 e Å−3 Δρmin = −0.44 e Å−3 Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. pan class="Chemical">Crystal structure: contains datablock(s) I, New_Global_Publ_Block, global. DOI: 10.1107/S1600536812007295/lh5417sup1.cif Strupan class="Chemical">cture factors: contains datablock(s) I. DOI: 10.1107/S1600536812007295/lh5417Isup2.hkl Additional supplementary materials: pan class="Chemical">crystallograpn>hipan class="Chemical">c information; 3D view; checkCIF report
[Pd(CH3)Cl(C24H20NPS)]F(000) = 2192
Mr = 542.32Dx = 1.598 Mg m−3
Monoclinic, C2/cCu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2ycCell parameters from 9937 reflections
a = 24.6534 (4) Åθ = 3.6–72.0°
b = 10.0118 (1) ŵ = 9.35 mm−1
c = 18.4507 (3) ÅT = 100 K
β = 98.027 (1)°Plate, yellow
V = 4509.47 (11) Å30.26 × 0.15 × 0.08 mm
Z = 8
Bruker SMART CCD APEXII diffractometer4048 independent reflections
Radiation source: fine-focus sealed tube3919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 71.9°, θmin = 3.6°
Absorption correction: numerical (SADABS; Sheldrick, 2008a)h = −29→28
Tmin = 0.195, Tmax = 0.522k = −11→11
22554 measured reflectionsl = −21→22
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.024Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0291P)2 + 12.1978P] where P = (Fo2 + 2Fc2)/3
4048 reflections(Δ/σ)max < 0.001
272 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Experimental. crystal mounted on a Cryoloop using Paratone-N
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
xyzUiso*/Ueq
Pd10.111634 (7)0.271512 (17)0.253204 (8)0.01132 (7)
Cl10.10246 (2)0.09406 (6)0.33614 (3)0.02005 (13)
S10.08000 (3)−0.00649 (6)0.02911 (3)0.02051 (14)
P10.11772 (2)0.45419 (6)0.18890 (3)0.01083 (12)
N10.04735 (8)0.1992 (2)0.17213 (11)0.0150 (4)
C10.05000 (9)0.5072 (2)0.14458 (12)0.0125 (5)
C20.00859 (9)0.4126 (2)0.12111 (12)0.0140 (5)
C3−0.04027 (10)0.4576 (3)0.08017 (13)0.0178 (5)
H3−0.06820.39480.06370.021*
C4−0.04872 (10)0.5906 (3)0.06324 (13)0.0194 (5)
H4−0.08230.61880.03590.023*
C5−0.00817 (10)0.6833 (3)0.08607 (14)0.0192 (5)
H5−0.01380.77520.07440.023*
C60.04080 (10)0.6410 (3)0.12609 (13)0.0161 (5)
H60.06860.70480.14120.019*
C70.01250 (10)0.2671 (2)0.12986 (13)0.0153 (5)
H7−0.01460.21670.09990.018*
C80.04345 (10)0.0513 (2)0.16373 (14)0.0180 (5)
H8A0.00750.02720.13610.022*
H8B0.04640.00890.21260.022*
C90.08836 (10)0.0011 (2)0.12399 (13)0.0162 (5)
C100.14046 (10)−0.0368 (2)0.15316 (14)0.0178 (5)
H100.1533−0.03920.20410.021*
C110.17293 (10)−0.0723 (3)0.09775 (14)0.0197 (5)
H110.2099−0.10130.10830.024*
C120.14600 (11)−0.0609 (3)0.02862 (15)0.0217 (5)
H120.1616−0.0804−0.01440.026*
C130.17473 (10)0.3382 (3)0.32856 (13)0.0194 (5)
H13A0.19280.26190.35500.029*
H13B0.16030.39810.36330.029*
H13C0.20120.38650.30340.029*
C140.15438 (9)0.4419 (2)0.10996 (12)0.0127 (5)
C150.16901 (10)0.5568 (3)0.07414 (13)0.0160 (5)
H150.16190.64270.09260.019*
C160.19398 (10)0.5452 (3)0.01147 (13)0.0181 (5)
H160.20480.6232−0.01220.022*
C170.20320 (10)0.4202 (3)−0.01671 (13)0.0179 (5)
H170.21980.4127−0.06000.021*
C180.18818 (9)0.3060 (3)0.01822 (13)0.0156 (5)
H180.19420.2205−0.00150.019*
C190.16432 (9)0.3164 (2)0.08196 (13)0.0133 (5)
H190.15480.23800.10640.016*
C200.14646 (10)0.5991 (2)0.23982 (12)0.0138 (5)
C210.11485 (10)0.6668 (2)0.28528 (13)0.0156 (5)
H210.07760.64300.28530.019*
C220.13771 (11)0.7685 (2)0.33021 (14)0.0190 (5)
H220.11590.81490.36060.023*
C230.19234 (11)0.8030 (3)0.33115 (13)0.0203 (5)
H230.20780.87380.36160.024*
C240.22424 (11)0.7342 (3)0.28783 (14)0.0202 (5)
H240.26180.75670.28930.024*
C250.20175 (10)0.6324 (3)0.24205 (13)0.0169 (5)
H250.22390.58560.21230.020*
U11U22U33U12U13U23
Pd10.01188 (10)0.01295 (11)0.00892 (10)0.00129 (6)0.00075 (7)0.00036 (6)
Cl10.0251 (3)0.0184 (3)0.0173 (3)0.0039 (2)0.0054 (2)0.0064 (2)
S10.0201 (3)0.0235 (3)0.0165 (3)0.0007 (2)−0.0027 (2)−0.0013 (2)
P10.0099 (3)0.0129 (3)0.0091 (3)−0.0002 (2)−0.0006 (2)−0.0002 (2)
N10.0142 (10)0.0149 (10)0.0162 (10)−0.0028 (8)0.0028 (8)−0.0019 (8)
C10.0117 (11)0.0174 (12)0.0083 (10)0.0009 (9)0.0007 (9)−0.0002 (9)
C20.0117 (11)0.0205 (13)0.0101 (11)−0.0001 (9)0.0027 (9)−0.0012 (9)
C30.0115 (11)0.0260 (14)0.0156 (12)−0.0014 (10)0.0012 (10)−0.0017 (10)
C40.0133 (12)0.0299 (14)0.0143 (12)0.0058 (10)−0.0010 (10)0.0014 (10)
C50.0204 (13)0.0197 (13)0.0178 (12)0.0043 (10)0.0032 (10)0.0038 (10)
C60.0146 (12)0.0186 (13)0.0146 (11)−0.0005 (9)0.0005 (10)−0.0001 (10)
C70.0113 (12)0.0205 (13)0.0145 (12)−0.0027 (9)0.0032 (10)−0.0036 (9)
C80.0187 (12)0.0134 (12)0.0218 (13)−0.0023 (10)0.0027 (10)−0.0017 (10)
C90.0194 (12)0.0124 (12)0.0158 (12)−0.0040 (9)−0.0013 (10)0.0011 (9)
C100.0236 (13)0.0099 (12)0.0205 (12)0.0000 (10)0.0048 (11)0.0024 (10)
C110.0177 (12)0.0160 (13)0.0248 (13)0.0013 (10)0.0004 (10)−0.0006 (10)
C120.0248 (13)0.0190 (13)0.0215 (13)0.0009 (11)0.0043 (11)−0.0014 (10)
C130.0216 (13)0.0221 (14)0.0118 (11)−0.0003 (10)−0.0067 (10)−0.0014 (10)
C140.0097 (10)0.0178 (12)0.0098 (11)−0.0005 (9)−0.0020 (9)−0.0006 (9)
C150.0176 (12)0.0172 (13)0.0123 (11)0.0003 (10)−0.0009 (10)−0.0010 (9)
C160.0195 (12)0.0208 (13)0.0135 (12)−0.0031 (10)0.0006 (10)0.0042 (10)
C170.0138 (11)0.0278 (14)0.0117 (11)0.0012 (10)0.0011 (10)−0.0001 (10)
C180.0113 (11)0.0189 (12)0.0157 (12)0.0032 (9)−0.0018 (9)−0.0022 (10)
C190.0079 (10)0.0164 (12)0.0143 (11)0.0015 (9)−0.0033 (9)0.0019 (9)
C200.0168 (12)0.0136 (12)0.0099 (11)−0.0014 (9)−0.0021 (9)0.0008 (9)
C210.0161 (12)0.0167 (13)0.0135 (11)0.0002 (9)0.0003 (9)0.0019 (9)
C220.0292 (14)0.0149 (12)0.0127 (12)0.0032 (10)0.0027 (11)0.0005 (9)
C230.0310 (14)0.0143 (12)0.0130 (12)−0.0059 (11)−0.0059 (11)0.0013 (10)
C240.0180 (13)0.0258 (14)0.0147 (12)−0.0075 (10)−0.0048 (10)0.0032 (10)
C250.0160 (12)0.0211 (13)0.0129 (11)0.0001 (10)−0.0003 (9)0.0002 (10)
Pd1—C132.048 (2)C11—C121.358 (4)
Pd1—N12.147 (2)C11—H110.9500
Pd1—P12.1965 (6)C12—H120.9500
Pd1—Cl12.3761 (6)C13—H13A0.9800
S1—C121.717 (3)C13—H13B0.9800
S1—C91.736 (2)C13—H13C0.9800
P1—C201.817 (2)C14—C191.394 (3)
P1—C141.822 (2)C14—C151.399 (3)
P1—C11.832 (2)C15—C161.389 (3)
N1—C71.273 (3)C15—H150.9500
N1—C81.490 (3)C16—C171.386 (4)
C1—C61.393 (4)C16—H160.9500
C1—C21.416 (3)C17—C181.388 (4)
C2—C31.404 (3)C17—H170.9500
C2—C71.467 (3)C18—C191.390 (3)
C3—C41.377 (4)C18—H180.9500
C3—H30.9500C19—H190.9500
C4—C51.386 (4)C20—C211.398 (3)
C4—H40.9500C20—C251.399 (3)
C5—C61.390 (3)C21—C221.382 (4)
C5—H50.9500C21—H210.9500
C6—H60.9500C22—C231.388 (4)
C7—H70.9500C22—H220.9500
C8—C91.498 (3)C23—C241.381 (4)
C8—H8A0.9900C23—H230.9500
C8—H8B0.9900C24—C251.389 (4)
C9—C101.375 (4)C24—H240.9500
C10—C111.428 (4)C25—H250.9500
C10—H100.9500
C13—Pd1—N1178.18 (9)C12—C11—C10113.7 (2)
C13—Pd1—P189.57 (8)C12—C11—H11123.2
N1—Pd1—P190.23 (6)C10—C11—H11123.2
C13—Pd1—Cl186.45 (8)C11—C12—S1111.2 (2)
N1—Pd1—Cl193.96 (6)C11—C12—H12124.4
P1—Pd1—Cl1171.99 (2)S1—C12—H12124.4
C12—S1—C992.29 (12)Pd1—C13—H13A109.5
C20—P1—C14105.43 (11)Pd1—C13—H13B109.5
C20—P1—C1105.36 (11)H13A—C13—H13B109.5
C14—P1—C1100.70 (10)Pd1—C13—H13C109.5
C20—P1—Pd1115.88 (8)H13A—C13—H13C109.5
C14—P1—Pd1117.03 (8)H13B—C13—H13C109.5
C1—P1—Pd1110.82 (8)C19—C14—C15119.8 (2)
C7—N1—C8116.0 (2)C19—C14—P1119.31 (18)
C7—N1—Pd1128.02 (17)C15—C14—P1120.75 (18)
C8—N1—Pd1115.98 (15)C16—C15—C14119.9 (2)
C6—C1—C2118.9 (2)C16—C15—H15120.1
C6—C1—P1119.66 (18)C14—C15—H15120.1
C2—C1—P1121.07 (18)C17—C16—C15120.2 (2)
C3—C2—C1118.5 (2)C17—C16—H16119.9
C3—C2—C7114.6 (2)C15—C16—H16119.9
C1—C2—C7126.7 (2)C16—C17—C18120.1 (2)
C4—C3—C2121.6 (2)C16—C17—H17120.0
C4—C3—H3119.2C18—C17—H17120.0
C2—C3—H3119.2C17—C18—C19120.2 (2)
C3—C4—C5119.9 (2)C17—C18—H18119.9
C3—C4—H4120.0C19—C18—H18119.9
C5—C4—H4120.0C18—C19—C14119.9 (2)
C4—C5—C6119.5 (2)C18—C19—H19120.1
C4—C5—H5120.2C14—C19—H19120.1
C6—C5—H5120.2C21—C20—C25119.3 (2)
C5—C6—C1121.5 (2)C21—C20—P1119.21 (18)
C5—C6—H6119.2C25—C20—P1120.93 (18)
C1—C6—H6119.2C22—C21—C20120.2 (2)
N1—C7—C2128.7 (2)C22—C21—H21119.9
N1—C7—H7115.6C20—C21—H21119.9
C2—C7—H7115.6C21—C22—C23120.3 (2)
N1—C8—C9110.1 (2)C21—C22—H22119.9
N1—C8—H8A109.6C23—C22—H22119.9
C9—C8—H8A109.6C24—C23—C22119.9 (2)
N1—C8—H8B109.6C24—C23—H23120.0
C9—C8—H8B109.6C22—C23—H23120.0
H8A—C8—H8B108.2C23—C24—C25120.4 (2)
C10—C9—C8128.0 (2)C23—C24—H24119.8
C10—C9—S1110.83 (19)C25—C24—H24119.8
C8—C9—S1121.11 (18)C24—C25—C20119.9 (2)
C9—C10—C11112.0 (2)C24—C25—H25120.1
C9—C10—H10124.0C20—C25—H25120.1
C11—C10—H10124.0
C13—Pd1—P1—C20−25.48 (12)N1—C8—C9—C1088.4 (3)
N1—Pd1—P1—C20156.33 (10)N1—C8—C9—S1−87.7 (2)
Cl1—Pd1—P1—C2034.72 (19)C12—S1—C9—C100.2 (2)
C13—Pd1—P1—C1499.93 (11)C12—S1—C9—C8176.9 (2)
N1—Pd1—P1—C14−78.26 (10)C8—C9—C10—C11−176.7 (2)
Cl1—Pd1—P1—C14160.13 (16)S1—C9—C10—C11−0.3 (3)
C13—Pd1—P1—C1−145.43 (11)C9—C10—C11—C120.3 (3)
N1—Pd1—P1—C136.37 (10)C10—C11—C12—S1−0.1 (3)
Cl1—Pd1—P1—C1−85.23 (18)C9—S1—C12—C11−0.1 (2)
C13—Pd1—N1—C7−113 (3)C20—P1—C14—C19147.04 (18)
P1—Pd1—N1—C7−29.4 (2)C1—P1—C14—C19−103.59 (19)
Cl1—Pd1—N1—C7143.8 (2)Pd1—P1—C14—C1916.6 (2)
C13—Pd1—N1—C866 (3)C20—P1—C14—C15−37.7 (2)
P1—Pd1—N1—C8149.87 (16)C1—P1—C14—C1571.7 (2)
Cl1—Pd1—N1—C8−36.96 (16)Pd1—P1—C14—C15−168.13 (16)
C20—P1—C1—C628.9 (2)C19—C14—C15—C16−0.8 (3)
C14—P1—C1—C6−80.5 (2)P1—C14—C15—C16−176.12 (18)
Pd1—P1—C1—C6154.97 (17)C14—C15—C16—C171.6 (4)
C20—P1—C1—C2−158.43 (18)C15—C16—C17—C18−0.9 (4)
C14—P1—C1—C292.1 (2)C16—C17—C18—C19−0.6 (4)
Pd1—P1—C1—C2−32.4 (2)C17—C18—C19—C141.4 (3)
C6—C1—C2—C3−0.2 (3)C15—C14—C19—C18−0.7 (3)
P1—C1—C2—C3−172.87 (17)P1—C14—C19—C18174.69 (17)
C6—C1—C2—C7174.5 (2)C14—P1—C20—C21155.04 (18)
P1—C1—C2—C71.8 (3)C1—P1—C20—C2149.0 (2)
C1—C2—C3—C4−0.6 (4)Pd1—P1—C20—C21−73.8 (2)
C7—C2—C3—C4−175.9 (2)C14—P1—C20—C25−33.8 (2)
C2—C3—C4—C50.7 (4)C1—P1—C20—C25−139.78 (19)
C3—C4—C5—C6−0.1 (4)Pd1—P1—C20—C2597.34 (19)
C4—C5—C6—C1−0.7 (4)C25—C20—C21—C222.0 (4)
C2—C1—C6—C50.8 (4)P1—C20—C21—C22173.29 (18)
P1—C1—C6—C5173.59 (19)C20—C21—C22—C23−0.7 (4)
C8—N1—C7—C2−174.8 (2)C21—C22—C23—C24−1.0 (4)
Pd1—N1—C7—C24.4 (4)C22—C23—C24—C251.4 (4)
C3—C2—C7—N1−168.7 (2)C23—C24—C25—C20−0.1 (4)
C1—C2—C7—N116.5 (4)C21—C20—C25—C24−1.6 (4)
C7—N1—C8—C9104.4 (2)P1—C20—C25—C24−172.73 (19)
Pd1—N1—C8—C9−74.9 (2)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Chlorido{N-[2-(diphenylphosphanyl)benz-ylidene]-2-(2-thienyl)ethanamine-κN,P}methylpalladium(II) dichloromethane hemisolvate.

Authors:  Martin O Onani; William M Motswainyana; Emmanuel I Iwuoha; James Darkwa; Roger A Lalancette
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-22
  2 in total

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