Bis­[(S)-(–)-1-phenyl­ethyl­ammonium] tetra­chloro­palladate(II)

In the title compound, (C₈H₁₂N)₂[PdCl₄], the ammonium functionality is involved in three bifurcated hydrogen contacts with the Cl atoms of symmetry-related tetra­chloro­palladate anions, with H...Cl separations in the range 2.48 (3)–2.95 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.028
• wR factor = 0.074
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT390_ALERT_3_B Deviating Methyl C2      X-C-H Bond Angle ......      98.00 Deg.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor ....       2.58
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CL1      =       2.95 Ang.
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.856(19) ......       2.11 su-Rat
              N1   -H11     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.860(19) ......       2.11 su-Rat
              N1   -H12     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.98(5), Rep     0.98(2) ......       2.50 su-Rat
              C2   -H21     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.856(19) ......       2.11 su-Rat
              N1   -H11     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.856(19) ......       2.11 su-Rat
              N1   -H11     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.860(19) ......       2.11 su-Rat
              N1   -H12     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.860(19) ......       2.11 su-Rat
              N1   -H12     1.555   1.555

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           29.99
           From the CIF: _reflns_number_total               1904
           Count of symmetry unique reflns         1676
           Completeness (_total/calc)            113.60%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       228
           Fraction of Friedel pairs measured     0.136
           Are heavy atom types Z>Si present          yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  13 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

(S)-(-)-1-Phenylethylammonium tetrachloropalladate(II)

Crystal data

(C8H12N)2[PdCl4]	F(000) = 496
Mr = 492.57	Dx = 1.526 Mg m^−3
Monoclinic, C2	Melting point: 463 K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 11.2280 (11) Å	Cell parameters from 79 reflections
b = 7.2220 (11) Å	θ = 4.6–13.0°
c = 13.3393 (16) Å	µ = 1.36 mm^−1
β = 97.80 (1)°	T = 296 K
V = 1071.7 (2) Å^3	Plate, orange
Z = 2	0.60 × 0.28 × 0.08 mm

Data collection

Bruker P4 diffractometer	1836 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, FN4	Rint = 0.025
Graphite monochromator	θmax = 30.0°, θmin = 3.1°
2θ/ω scans	h = −15→3
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −1→10
Tmin = 0.643, Tmax = 0.898	l = −18→18
2431 measured reflections	3 standard reflections every 97 reflections
1904 independent reflections	intensity decay: <1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.074	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 0.1903P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1904 reflections	Δρmax = 0.51 e Å^−3
125 parameters	Δρmin = −1.17 e Å^−3
7 restraints	Absolute structure: Flack (1983), 227 Friedel pairs
Primary atom site location: heavy-atom method	Absolute structure parameter: −0.01 (4)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Pd1	0.5000	0.61456 (9)	0.5000	0.03668 (9)
Cl1	0.59668 (18)	0.84213 (12)	0.42090 (15)	0.0469 (3)
Cl2	0.58619 (19)	0.38868 (15)	0.41181 (17)	0.0536 (4)
C1	0.3641 (3)	0.0700 (5)	0.2733 (2)	0.0463 (8)
H1A	0.4512	0.0674	0.2725	0.056*
N1	0.3428 (2)	0.1143 (10)	0.37981 (16)	0.0444 (5)
H11	0.390 (4)	0.205 (5)	0.399 (4)	0.057 (7)*
H12	0.361 (4)	0.023 (6)	0.420 (3)	0.057 (7)*
H13	0.268 (2)	0.134 (10)	0.389 (3)	0.057 (7)*
C2	0.3161 (6)	−0.1224 (8)	0.2451 (4)	0.0672 (12)
H21	0.349 (5)	−0.136 (9)	0.181 (3)	0.066 (9)*
H22	0.2290 (19)	−0.127 (9)	0.234 (4)	0.066 (9)*
H23	0.351 (5)	−0.224 (6)	0.289 (3)	0.066 (9)*
C3	0.3133 (4)	0.2192 (6)	0.2021 (3)	0.0533 (8)
C4	0.3890 (7)	0.3280 (9)	0.1525 (4)	0.0802 (17)
H4A	0.4718	0.3112	0.1649	0.096*
C5	0.3397 (11)	0.4637 (11)	0.0833 (5)	0.115 (3)
H5A	0.3905	0.5372	0.0507	0.138*
C6	0.2194 (11)	0.4886 (10)	0.0638 (4)	0.122 (4)
H6A	0.1880	0.5768	0.0167	0.146*
C7	0.1437 (8)	0.3843 (12)	0.1131 (4)	0.099 (3)
H7A	0.0612	0.4046	0.1010	0.119*
C8	0.1900 (5)	0.2477 (9)	0.1815 (3)	0.0704 (13)
H8A	0.1380	0.1753	0.2135	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.03646 (13)	0.03294 (13)	0.03924 (13)	0.000	0.00010 (8)	0.000
Cl1	0.0515 (7)	0.0392 (6)	0.0513 (6)	−0.0028 (5)	0.0116 (5)	0.0002 (5)
Cl2	0.0541 (8)	0.0409 (7)	0.0681 (9)	−0.0051 (6)	0.0163 (6)	−0.0142 (6)
C1	0.0498 (14)	0.047 (2)	0.0430 (13)	0.0004 (12)	0.0080 (11)	−0.0019 (12)
N1	0.0487 (11)	0.0464 (12)	0.0367 (9)	0.001 (3)	0.0004 (8)	0.002 (2)
C2	0.091 (3)	0.050 (2)	0.058 (2)	−0.003 (2)	0.000 (2)	−0.0122 (19)
C3	0.077 (2)	0.048 (2)	0.0351 (13)	0.0007 (18)	0.0091 (14)	−0.0041 (15)
C4	0.119 (5)	0.067 (3)	0.055 (2)	−0.028 (3)	0.016 (3)	0.000 (2)
C5	0.222 (11)	0.066 (4)	0.057 (3)	−0.026 (5)	0.017 (4)	0.014 (3)
C6	0.235 (12)	0.074 (4)	0.047 (2)	0.041 (6)	−0.020 (4)	0.008 (3)
C7	0.134 (6)	0.107 (5)	0.051 (2)	0.057 (5)	−0.012 (3)	−0.003 (3)
C8	0.083 (3)	0.083 (4)	0.0433 (16)	0.023 (3)	0.0023 (18)	0.002 (2)

Geometric parameters (Å, º)

Pd1—Cl1	2.3030 (17)	C2—H23	0.99 (2)
Pd1—Cl2	2.3001 (18)	C3—C8	1.390 (7)
Pd1—Cl1^i	2.3030 (16)	C3—C4	1.390 (7)
Pd1—Cl2^i	2.3001 (18)	C4—C5	1.406 (10)
C1—N1	1.506 (4)	C4—H4A	0.9300
C1—C2	1.519 (6)	C5—C6	1.353 (13)
C1—C3	1.497 (5)	C5—H5A	0.9300
C1—H1A	0.9800	C6—C7	1.369 (12)
N1—H11	0.856 (19)	C6—H6A	0.9300
N1—H12	0.860 (19)	C7—C8	1.395 (8)
N1—H13	0.872 (19)	C7—H7A	0.9300
C2—H21	0.98 (2)	C8—H8A	0.9300
C2—H22	0.970 (19)
Cl2^i—Pd1—Cl2	89.66 (9)	H21—C2—H22	111 (5)
Cl2^i—Pd1—Cl1^i	90.84 (3)	H21—C2—H23	106 (5)
Cl2—Pd1—Cl1^i	176.08 (10)	H22—C2—H23	112 (5)
Cl2^i—Pd1—Cl1	176.08 (10)	C8—C3—C4	118.6 (5)
Cl2—Pd1—Cl1	90.84 (3)	C8—C3—C1	121.0 (4)
Cl1^i—Pd1—Cl1	88.94 (8)	C4—C3—C1	120.3 (5)
C3—C1—N1	110.5 (3)	C3—C4—C5	119.6 (8)
C3—C1—C2	114.2 (3)	C3—C4—H4A	120.2
N1—C1—C2	109.4 (4)	C5—C4—H4A	120.2
C3—C1—H1A	107.5	C6—C5—C4	120.9 (8)
N1—C1—H1A	107.5	C6—C5—H5A	119.6
C2—C1—H1A	107.5	C4—C5—H5A	119.6
C1—N1—H11	106 (3)	C5—C6—C7	120.2 (6)
C1—N1—H12	112 (4)	C5—C6—H6A	119.9
C1—N1—H13	116 (3)	C7—C6—H6A	119.9
H11—N1—H12	109 (4)	C6—C7—C8	120.2 (7)
H11—N1—H13	113 (6)	C6—C7—H7A	119.9
H12—N1—H13	101 (5)	C8—C7—H7A	119.9
C1—C2—H21	98 (4)	C3—C8—C7	120.5 (6)
C1—C2—H22	113 (4)	C3—C8—H8A	119.8
C1—C2—H23	116 (3)	C7—C8—H8A	119.8
N1—C1—C3—C8	−67.6 (5)	C3—C4—C5—C6	−0.6 (10)
C2—C1—C3—C8	56.2 (5)	C4—C5—C6—C7	1.5 (11)
N1—C1—C3—C4	114.7 (4)	C5—C6—C7—C8	−2.0 (10)
C2—C1—C3—C4	−121.5 (5)	C4—C3—C8—C7	−0.7 (7)
C8—C3—C4—C5	0.2 (8)	C1—C3—C8—C7	−178.4 (5)
C1—C3—C4—C5	178.0 (5)	C6—C7—C8—C3	1.6 (9)

Symmetry code: (i) −x+1, y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···Cl2	0.86 (2)	2.56 (3)	3.356 (5)	155 (4)
N1—H11···Cl2^i	0.86 (2)	2.83 (4)	3.419 (5)	127 (4)
N1—H12···Cl1^ii	0.86 (2)	2.48 (3)	3.302 (5)	160 (5)
N1—H12···Cl1^iii	0.86 (2)	2.95 (4)	3.444 (5)	119 (4)
N1—H13···Cl1^iv	0.87 (2)	2.53 (4)	3.325 (5)	153 (7)
N1—H13···Cl2^iv	0.87 (2)	2.76 (6)	3.387 (5)	130 (6)

Symmetry codes: (i) −x+1, y, −z+1; (ii) −x+1, y−1, −z+1; (iii) x, y−1, z; (iv) x−1/2, y−1/2, z.