trans-Dichloro­bis[(S)-(-)-1-(1-naphth­yl)ethyl­amine]palladium(II)

The title complex, [PdCl₂(C₁₂H₁₃N₂)₂], has two amine ligands coordinated in such a way that the naphthyl and methyl groups are located in the same hemisphere with respect to the [PdN₂Cl₂] coordination plane. This configuration allows for the formation of dimers in the solid state with a metal-metal separation of 3.2499 (4) Å.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.028
• wR factor = 0.075
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pd1    -   Cl1     ..       6.03 su
PLAT420_ALERT_2_C D-H Without Acceptor       N1     -   H1A    ...          ?
PLAT420_ALERT_2_C D-H Without Acceptor       N14    -   H14B   ...          ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1A    ..  CL1     ..       2.89 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H14B   ..  CL2     ..       2.86 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           29.99
           From the CIF: _reflns_number_total               5769
           Count of symmetry unique reflns         3578
           Completeness (_total/calc)            161.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2191
           Fraction of Friedel pairs measured     0.612
           Are heavy atom types Z>Si present        yes

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

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

---

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.

trans-Dichlorobis[(S)-(-)-1-(1-naphthyl)ethylamine]palladium(II)

Crystal data

[PdCl2(C12H13N2)2]	F(000) = 1056
Mr = 519.77	Dx = 1.518 Mg m^−3
Monoclinic, C2	Melting point = 501–503 K
Hall symbol: C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 35.310 (3) Å	Cell parameters from 94 reflections
b = 6.7996 (7) Å	θ = 4.7–13.6°
c = 9.7193 (7) Å	µ = 1.06 mm^−1
β = 102.893 (4)°	T = 296 K
V = 2274.7 (3) Å^3	Plate, orange
Z = 4	0.50 × 0.20 × 0.08 mm

Data collection

Bruker P4 diffractometer	5658 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube, FN4	Rint = 0.021
Graphite monochromator	θmax = 30.0°, θmin = 2.2°
ω scans	h = −49→1
Absorption correction: ψ scan (XSCANS; Siemens, 1996)	k = −9→6
Tmin = 0.566, Tmax = 0.920	l = −13→13
6025 measured reflections	2 standard reflections every 48 reflections
5769 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: See text
R[F^2 > 2σ(F^2)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.075	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.3281P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.003
5769 reflections	Δρmax = 0.36 e Å^−3
274 parameters	Δρmin = −1.02 e Å^−3
5 restraints	Absolute structure: Flack (1983), 2217 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (2)

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.

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

	x	y	z	Uiso*/Ueq
Pd1	0.495349 (4)	0.31324 (4)	0.162605 (14)	0.02863 (5)
Cl1	0.45490 (2)	0.04223 (11)	0.13398 (8)	0.03943 (15)
Cl2	0.53499 (2)	0.58458 (12)	0.19487 (9)	0.04372 (16)
N1	0.44808 (6)	0.4992 (4)	0.1243 (2)	0.0325 (4)
H1A	0.4571 (11)	0.617 (4)	0.125 (5)	0.049*
H1B	0.4350 (9)	0.483 (6)	0.042 (2)	0.049*
C2	0.42371 (7)	0.4965 (4)	0.2325 (2)	0.0329 (4)
H2A	0.4177	0.3588	0.2485	0.039*
C3	0.38533 (7)	0.6030 (4)	0.1787 (3)	0.0352 (5)
C4	0.35585 (7)	0.5138 (4)	0.0709 (3)	0.0361 (5)
C5	0.36046 (7)	0.3298 (6)	0.0083 (3)	0.0447 (6)
H5A	0.3835	0.2604	0.0379	0.054*
C6	0.33131 (11)	0.2521 (6)	−0.0957 (4)	0.0591 (9)
H6A	0.3349	0.1315	−0.1360	0.071*
C7	0.29597 (10)	0.3542 (8)	−0.1413 (4)	0.0679 (12)
H7A	0.2765	0.3021	−0.2127	0.081*
C8	0.29041 (9)	0.5263 (7)	−0.0818 (4)	0.0623 (10)
H8A	0.2667	0.5899	−0.1110	0.075*
C9	0.31964 (8)	0.6148 (6)	0.0246 (3)	0.0471 (7)
C10	0.31380 (9)	0.7976 (7)	0.0864 (4)	0.0591 (8)
H10A	0.2902	0.8622	0.0569	0.071*
C11	0.34224 (11)	0.8810 (6)	0.1885 (4)	0.0595 (9)
H11A	0.3381	1.0018	0.2276	0.071*
C12	0.37792 (9)	0.7816 (5)	0.2340 (3)	0.0472 (7)
H12A	0.3971	0.8388	0.3038	0.057*
C13	0.44874 (8)	0.5757 (6)	0.3700 (3)	0.0460 (6)
H13A	0.4721	0.4995	0.3956	0.069*
H13B	0.4346	0.5668	0.4434	0.069*
H13C	0.4552	0.7107	0.3573	0.069*
N14	0.54304 (7)	0.1276 (4)	0.2016 (2)	0.0334 (4)
H14A	0.5540 (10)	0.125 (7)	0.132 (3)	0.050*
H14B	0.5379 (12)	0.005 (3)	0.206 (5)	0.050*
C15	0.57083 (6)	0.1594 (4)	0.3391 (2)	0.0319 (5)
H15A	0.5757	0.3010	0.3505	0.038*
C16	0.60979 (6)	0.0571 (4)	0.3498 (3)	0.0341 (5)
C17	0.64378 (6)	0.1363 (4)	0.4442 (3)	0.0352 (5)
C18	0.64390 (7)	0.3150 (7)	0.5185 (3)	0.0458 (5)
H18A	0.6210	0.3865	0.5077	0.055*
C19	0.67731 (9)	0.3861 (6)	0.6070 (3)	0.0547 (8)
H19A	0.6768	0.5041	0.6549	0.066*
C20	0.71216 (8)	0.2778 (8)	0.6241 (3)	0.0598 (11)
H20A	0.7347	0.3247	0.6839	0.072*
C21	0.71307 (8)	0.1067 (7)	0.5544 (4)	0.0574 (9)
H21A	0.7363	0.0378	0.5670	0.069*
C22	0.67929 (7)	0.0291 (5)	0.4619 (3)	0.0420 (6)
C23	0.68054 (8)	−0.1490 (6)	0.3891 (4)	0.0556 (9)
H23A	0.7036	−0.2198	0.4035	0.067*
C24	0.64816 (9)	−0.2188 (5)	0.2975 (4)	0.0552 (8)
H24A	0.6493	−0.3354	0.2485	0.066*
C25	0.61296 (8)	−0.1123 (5)	0.2778 (4)	0.0456 (6)
H25A	0.5912	−0.1592	0.2136	0.055*
C26	0.55147 (8)	0.0926 (6)	0.4552 (3)	0.0497 (7)
H26A	0.5271	0.1592	0.4458	0.075*
H26B	0.5679	0.1230	0.5453	0.075*
H26C	0.5471	−0.0467	0.4480	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02273 (7)	0.03088 (9)	0.03057 (7)	0.00039 (6)	0.00235 (4)	0.00135 (6)
Cl1	0.0332 (3)	0.0336 (4)	0.0501 (3)	−0.0034 (3)	0.0064 (2)	0.0022 (3)
Cl2	0.0354 (3)	0.0358 (4)	0.0571 (4)	−0.0065 (3)	0.0044 (3)	0.0003 (3)
N1	0.0272 (9)	0.0334 (13)	0.0363 (9)	0.0036 (9)	0.0055 (7)	0.0043 (9)
C2	0.0281 (9)	0.0359 (13)	0.0340 (9)	−0.0001 (8)	0.0055 (8)	0.0015 (9)
C3	0.0300 (10)	0.0361 (13)	0.0410 (11)	0.0007 (9)	0.0110 (8)	0.0010 (10)
C4	0.0273 (9)	0.0408 (14)	0.0405 (11)	0.0024 (9)	0.0084 (8)	0.0046 (10)
C5	0.0351 (10)	0.0483 (18)	0.0479 (11)	−0.0005 (13)	0.0036 (9)	−0.0042 (14)
C6	0.0539 (18)	0.066 (3)	0.0516 (16)	−0.0107 (16)	−0.0005 (13)	−0.0095 (15)
C7	0.0459 (15)	0.084 (4)	0.0629 (18)	−0.0120 (18)	−0.0111 (13)	0.0004 (19)
C8	0.0301 (12)	0.081 (3)	0.070 (2)	0.0029 (15)	−0.0028 (12)	0.014 (2)
C9	0.0311 (11)	0.057 (2)	0.0539 (14)	0.0074 (11)	0.0105 (10)	0.0139 (14)
C10	0.0422 (13)	0.057 (2)	0.082 (2)	0.0181 (17)	0.0213 (13)	0.015 (2)
C11	0.062 (2)	0.0453 (18)	0.079 (2)	0.0164 (15)	0.0324 (18)	−0.0020 (16)
C12	0.0459 (13)	0.0417 (19)	0.0573 (14)	0.0029 (12)	0.0185 (11)	−0.0044 (13)
C13	0.0419 (13)	0.0551 (19)	0.0388 (12)	−0.0041 (13)	0.0041 (10)	−0.0047 (12)
N14	0.0261 (9)	0.0390 (14)	0.0337 (9)	0.0030 (9)	0.0037 (7)	0.0016 (9)
C15	0.0223 (8)	0.0359 (13)	0.0350 (10)	0.0038 (8)	0.0012 (7)	0.0003 (8)
C16	0.0242 (9)	0.0358 (13)	0.0420 (11)	0.0034 (9)	0.0063 (8)	0.0041 (9)
C17	0.0244 (9)	0.0420 (14)	0.0381 (11)	0.0031 (9)	0.0049 (8)	0.0060 (10)
C18	0.0320 (9)	0.0553 (16)	0.0469 (11)	−0.0006 (15)	0.0023 (8)	−0.0062 (16)
C19	0.0417 (14)	0.070 (2)	0.0497 (14)	−0.0063 (14)	0.0045 (11)	−0.0122 (14)
C20	0.0292 (11)	0.091 (3)	0.0531 (14)	−0.0054 (15)	−0.0030 (10)	0.0005 (18)
C21	0.0244 (11)	0.081 (3)	0.0631 (18)	0.0048 (13)	0.0022 (11)	0.0115 (18)
C22	0.0258 (10)	0.0516 (18)	0.0483 (13)	0.0042 (10)	0.0079 (9)	0.0103 (12)
C23	0.0331 (11)	0.055 (2)	0.081 (2)	0.0161 (13)	0.0176 (12)	0.0073 (16)
C24	0.0412 (13)	0.038 (2)	0.089 (2)	0.0085 (12)	0.0219 (14)	−0.0069 (16)
C25	0.0315 (11)	0.0372 (14)	0.0672 (17)	0.0011 (10)	0.0088 (11)	−0.0039 (13)
C26	0.0379 (12)	0.074 (2)	0.0397 (12)	0.0128 (14)	0.0134 (10)	0.0108 (14)

Geometric parameters (Å, º)

Pd1—N1	2.061 (2)	C13—H13B	0.9600
Pd1—N14	2.071 (2)	C13—H13C	0.9600
Pd1—Cl2	2.2947 (8)	N14—C15	1.487 (3)
Pd1—Cl1	2.3099 (8)	N14—H14A	0.851 (18)
Pd1—Pd1^i	3.2499 (4)	N14—H14B	0.855 (19)
N1—C2	1.500 (3)	C15—C26	1.513 (4)
N1—H1A	0.865 (19)	C15—C16	1.524 (3)
N1—H1B	0.834 (18)	C15—H15A	0.9800
C2—C3	1.523 (3)	C16—C25	1.365 (4)
C2—C13	1.526 (4)	C16—C17	1.443 (3)
C2—H2A	0.9800	C17—C18	1.413 (5)
C3—C12	1.376 (4)	C17—C22	1.427 (3)
C3—C4	1.436 (4)	C18—C19	1.383 (4)
C4—C5	1.417 (5)	C18—H18A	0.9300
C4—C9	1.432 (4)	C19—C20	1.411 (5)
C5—C6	1.377 (4)	C19—H19A	0.9300
C5—H5A	0.9300	C20—C21	1.351 (6)
C6—C7	1.410 (6)	C20—H20A	0.9300
C6—H6A	0.9300	C21—C22	1.425 (4)
C7—C8	1.339 (7)	C21—H21A	0.9300
C7—H7A	0.9300	C22—C23	1.408 (5)
C8—C9	1.421 (5)	C23—C24	1.368 (5)
C8—H8A	0.9300	C23—H23A	0.9300
C9—C10	1.415 (6)	C24—C25	1.414 (4)
C10—C11	1.368 (6)	C24—H24A	0.9300
C10—H10A	0.9300	C25—H25A	0.9300
C11—C12	1.411 (4)	C26—H26A	0.9600
C11—H11A	0.9300	C26—H26B	0.9600
C12—H12A	0.9300	C26—H26C	0.9600
C13—H13A	0.9600
N1—Pd1—N14	179.70 (14)	C2—C13—H13B	109.5
N1—Pd1—Cl2	88.64 (7)	H13A—C13—H13B	109.5
N14—Pd1—Cl2	91.08 (9)	C2—C13—H13C	109.5
N1—Pd1—Cl1	90.78 (9)	H13A—C13—H13C	109.5
N14—Pd1—Cl1	89.50 (8)	H13B—C13—H13C	109.5
Cl2—Pd1—Cl1	178.81 (4)	C15—N14—Pd1	115.00 (18)
N1—Pd1—Pd1^i	94.47 (6)	C15—N14—H14A	113 (3)
N14—Pd1—Pd1^i	85.62 (6)	Pd1—N14—H14A	111 (3)
Cl2—Pd1—Pd1^i	86.67 (2)	C15—N14—H14B	102 (3)
Cl1—Pd1—Pd1^i	94.40 (2)	Pd1—N14—H14B	116 (3)
C2—N1—Pd1	115.74 (16)	H14A—N14—H14B	99 (4)
C2—N1—H1A	106 (3)	N14—C15—C26	108.0 (2)
Pd1—N1—H1A	107 (3)	N14—C15—C16	113.5 (2)
C2—N1—H1B	113 (3)	C26—C15—C16	111.3 (2)
Pd1—N1—H1B	110 (3)	N14—C15—H15A	107.9
H1A—N1—H1B	105 (4)	C26—C15—H15A	107.9
N1—C2—C3	111.06 (19)	C16—C15—H15A	107.9
N1—C2—C13	107.4 (2)	C25—C16—C17	119.3 (2)
C3—C2—C13	115.5 (2)	C25—C16—C15	121.7 (2)
N1—C2—H2A	107.6	C17—C16—C15	118.9 (2)
C3—C2—H2A	107.6	C18—C17—C22	118.4 (2)
C13—C2—H2A	107.6	C18—C17—C16	123.6 (2)
C12—C3—C4	119.2 (3)	C22—C17—C16	118.0 (3)
C12—C3—C2	121.2 (2)	C19—C18—C17	121.6 (3)
C4—C3—C2	119.6 (2)	C19—C18—H18A	119.2
C5—C4—C9	117.9 (3)	C17—C18—H18A	119.2
C5—C4—C3	123.6 (2)	C18—C19—C20	119.4 (4)
C9—C4—C3	118.5 (3)	C18—C19—H19A	120.3
C6—C5—C4	121.0 (3)	C20—C19—H19A	120.3
C6—C5—H5A	119.5	C21—C20—C19	120.5 (3)
C4—C5—H5A	119.5	C21—C20—H20A	119.7
C5—C6—C7	120.4 (4)	C19—C20—H20A	119.7
C5—C6—H6A	119.8	C20—C21—C22	121.7 (3)
C7—C6—H6A	119.8	C20—C21—H21A	119.2
C8—C7—C6	119.9 (3)	C22—C21—H21A	119.2
C8—C7—H7A	120.0	C23—C22—C21	121.3 (3)
C6—C7—H7A	120.0	C23—C22—C17	120.3 (3)
C7—C8—C9	122.1 (3)	C21—C22—C17	118.4 (3)
C7—C8—H8A	118.9	C24—C23—C22	120.7 (3)
C9—C8—H8A	118.9	C24—C23—H23A	119.7
C10—C9—C8	122.0 (3)	C22—C23—H23A	119.7
C10—C9—C4	119.5 (3)	C23—C24—C25	119.5 (3)
C8—C9—C4	118.6 (3)	C23—C24—H24A	120.3
C11—C10—C9	121.3 (3)	C25—C24—H24A	120.3
C11—C10—H10A	119.4	C16—C25—C24	122.2 (3)
C9—C10—H10A	119.4	C16—C25—H25A	118.9
C10—C11—C12	119.2 (3)	C24—C25—H25A	118.9
C10—C11—H11A	120.4	C15—C26—H26A	109.5
C12—C11—H11A	120.4	C15—C26—H26B	109.5
C3—C12—C11	122.3 (3)	H26A—C26—H26B	109.5
C3—C12—H12A	118.8	C15—C26—H26C	109.5
C11—C12—H12A	118.8	H26A—C26—H26C	109.5
C2—C13—H13A	109.5	H26B—C26—H26C	109.5
Cl2—Pd1—N1—C2	−113.03 (19)	Cl2—Pd1—N14—C15	55.92 (19)
Cl1—Pd1—N1—C2	65.94 (19)	Cl1—Pd1—N14—C15	−123.05 (19)
Pd1^i—Pd1—N1—C2	160.42 (19)	Pd1^i—Pd1—N14—C15	142.50 (19)
Pd1—N1—C2—C3	−167.58 (18)	Pd1—N14—C15—C26	70.0 (3)
Pd1—N1—C2—C13	65.3 (3)	Pd1—N14—C15—C16	−166.08 (17)
N1—C2—C3—C12	−109.4 (3)	N14—C15—C16—C25	−29.3 (4)
C13—C2—C3—C12	13.1 (4)	C26—C15—C16—C25	92.9 (3)
N1—C2—C3—C4	72.2 (3)	N14—C15—C16—C17	154.1 (2)
C13—C2—C3—C4	−165.3 (2)	C26—C15—C16—C17	−83.8 (3)
C12—C3—C4—C5	−179.4 (3)	C25—C16—C17—C18	177.1 (3)
C2—C3—C4—C5	−1.0 (4)	C15—C16—C17—C18	−6.2 (4)
C12—C3—C4—C9	0.1 (4)	C25—C16—C17—C22	−2.1 (4)
C2—C3—C4—C9	178.5 (2)	C15—C16—C17—C22	174.7 (2)
C9—C4—C5—C6	1.2 (4)	C22—C17—C18—C19	−0.2 (5)
C3—C4—C5—C6	−179.4 (3)	C16—C17—C18—C19	−179.4 (3)
C4—C5—C6—C7	−0.5 (5)	C17—C18—C19—C20	−0.1 (5)
C5—C6—C7—C8	−1.1 (6)	C18—C19—C20—C21	0.3 (6)
C6—C7—C8—C9	1.9 (6)	C19—C20—C21—C22	−0.1 (6)
C7—C8—C9—C10	179.4 (4)	C20—C21—C22—C23	179.7 (3)
C7—C8—C9—C4	−1.2 (5)	C20—C21—C22—C17	−0.3 (5)
C5—C4—C9—C10	179.1 (3)	C18—C17—C22—C23	−179.5 (3)
C3—C4—C9—C10	−0.4 (4)	C16—C17—C22—C23	−0.3 (4)
C5—C4—C9—C8	−0.4 (4)	C18—C17—C22—C21	0.4 (4)
C3—C4—C9—C8	−179.8 (3)	C16—C17—C22—C21	179.6 (3)
C8—C9—C10—C11	−179.9 (3)	C21—C22—C23—C24	−178.0 (3)
C4—C9—C10—C11	0.7 (5)	C17—C22—C23—C24	1.9 (5)
C9—C10—C11—C12	−0.6 (5)	C22—C23—C24—C25	−1.1 (5)
C4—C3—C12—C11	0.0 (4)	C17—C16—C25—C24	3.1 (4)
C2—C3—C12—C11	−178.4 (3)	C15—C16—C25—C24	−173.6 (3)
C10—C11—C12—C3	0.3 (5)	C23—C24—C25—C16	−1.5 (5)

Symmetry code: (i) −x+1, y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1^ii	0.87 (2)	2.89 (3)	3.700 (3)	156 (4)
N1—H1B···Cl2^i	0.83 (2)	2.83 (3)	3.339 (2)	121 (3)
N14—H14A···Cl1^i	0.85 (2)	2.60 (3)	3.330 (2)	145 (3)
N14—H14B···Cl2^iii	0.86 (2)	2.86 (2)	3.702 (3)	168 (4)

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