Structural characterization of the derivatives of bis­{[2,6-(di­methyl­amino)­meth­yl]phen­yl} selenide with palladium(II) and mercury(II)

The intra­molecularly coordinated homoleptic diorgano selenide bis­{2,6-bis­[(di­methyl­amino)­meth­yl]phen­yl} selenide, C₂₄H₃₈N₄Se or R₂Se, where R is 2,6-(Me₂NCH₂)₂C₆H₃, 14, was synthesized and its ligation reactions with Pd^II and Hg^II precursors were explored. The reaction of 14 with SO₂Cl₂ and K₂PdCl₄ resulted in the formation of the meta C—H-activated dipalladated com­plex {μ-2,2′-bis­[(di­methyl­amino)­meth­yl]-4,4′-bis­[(di­methyl­aza­nium­yl)meth­yl]-3,3′-selane­diyldiphenyl-κ⁴C¹,N²:C^1′,N^2′}bis­[di­chlorido­palladium(II)], [Pd₂Cl₄(C₂₄H₃₈N₄Se)] or [{R(H)PdCl₂}₂Se], 15. On the other hand, when ligand 14 was reacted with HgCl₂, the reaction afforded a dimercurated seleno­late com­plex, {μ-bis­{2,6-bis­[(di­methyl­amino)­meth­yl]benzene­selanolato-κ⁴N²,Se:Se,N⁶}-μ-chlorido-bis­[chlorido­mercury(II)], [Hg₂(C₁₂H₁₉N₂Se)Cl₃] or RSeHg₂Cl₃, 16, where two Hg^II ions are bridged by seleno­late and chloride ligands. In palladium com­plex 15, there are two mol­ecules located on crystallographic twofold axes and within each mol­ecule the Pd moieties are related by symmetry, but there are still two independent Pd centers. Mercury com­plex 16 results from the cleavage of one of the Se—C bonds to form a bifurcated SeHg₂ moiety with the formal charge on the Se atom being −1. In addition, one of the Cl ligands bridges the two Hg atoms and there are two terminal Hg—Cl bonds. Each Hg atom is in a distorted environment which can be best described as a T-shaped base with the bridging Cl atom in an apical position, with several angles close to 90° and with one angle much larger and closer to 180°.

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2019) for (14); APEX2 (Bruker, 2005) for (15), (16). Cell refinement: CrysAlis PRO (Rigaku OD, 2019) for (14); APEX2 (Bruker, 2005) for (15), (16). Data reduction: CrysAlis PRO (Rigaku OD, 2019) for (14); APEX2 (Bruker, 2005) for (15), (16). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (14); SUPERFLIP (Palatinus & Chapuis, 2007) for (15), (16). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis{2,6-bis[(dimethylamino)methyl]phenyl} selenide (14)

Crystal data

C24H38N4Se	F(000) = 976
Mr = 461.54	Dx = 1.241 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.9417 (3) Å	Cell parameters from 12119 reflections
b = 29.0031 (6) Å	θ = 2.3–27.3°
c = 10.2398 (3) Å	µ = 1.54 mm^−1
β = 111.572 (4)°	T = 120 K
V = 2469.55 (14) Å^3	Prism, orange
Z = 4	0.33 × 0.26 × 0.18 mm

Data collection

Rigaku Saturn 724 Dual Source CCD diffractometer	4617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.023
ω scans	θmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2019)	h = −10→10
Tmin = 0.653, Tmax = 0.786	k = −16→36
16025 measured reflections	l = −12→12
5013 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0259P)^2 + 1.2484P] where P = (Fo^2 + 2Fc^2)/3
5013 reflections	(Δ/σ)max = 0.002
270 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Se1	0.61845 (2)	0.33765 (2)	0.40458 (2)	0.01303 (5)
N1A	0.56051 (15)	0.29275 (4)	0.10664 (13)	0.0182 (3)
N2A	0.15431 (14)	0.39116 (4)	0.44403 (13)	0.0164 (2)
N1B	0.79086 (15)	0.29743 (4)	0.70261 (13)	0.0181 (3)
N2B	0.71373 (15)	0.48656 (4)	0.30274 (13)	0.0192 (3)
C1B	0.69907 (16)	0.38827 (5)	0.53679 (14)	0.0139 (3)
C1A	0.44067 (17)	0.36871 (4)	0.26112 (14)	0.0142 (3)
C2A	0.43523 (18)	0.36711 (5)	0.12159 (15)	0.0167 (3)
C2B	0.71804 (16)	0.37979 (5)	0.67768 (15)	0.0155 (3)
C3A	0.30749 (18)	0.38784 (5)	0.01577 (15)	0.0197 (3)
H3AA	0.302742	0.386715	−0.078396	0.024*
C3B	0.77076 (17)	0.41537 (5)	0.77507 (15)	0.0188 (3)
H3BA	0.782387	0.410085	0.869877	0.023*
C4A	0.18653 (19)	0.41021 (5)	0.04597 (16)	0.0214 (3)
H4AA	0.100523	0.424687	−0.026911	0.026*
C4B	0.80663 (18)	0.45856 (5)	0.73544 (16)	0.0213 (3)
H4BA	0.838598	0.482920	0.802017	0.026*
C5B	0.79562 (18)	0.46595 (5)	0.59858 (16)	0.0192 (3)
H5BA	0.823600	0.495252	0.572861	0.023*
C5A	0.19211 (18)	0.41128 (5)	0.18301 (16)	0.0189 (3)
H5AA	0.108984	0.426524	0.203087	0.023*
C6B	0.74393 (16)	0.43098 (5)	0.49733 (15)	0.0155 (3)
C6A	0.31754 (17)	0.39038 (5)	0.29232 (15)	0.0152 (3)
C7A	0.56599 (19)	0.34280 (5)	0.08725 (15)	0.0178 (3)
H7AA	0.552573	0.349415	−0.011275	0.021*
H7AB	0.672283	0.354743	0.148794	0.021*
C7B	0.68455 (18)	0.33272 (5)	0.72380 (15)	0.0172 (3)
H7BA	0.699518	0.333825	0.824473	0.021*
H7BB	0.571279	0.324237	0.669857	0.021*
C8A	0.7158 (2)	0.27148 (5)	0.12962 (16)	0.0236 (3)
H8AA	0.709310	0.238288	0.144620	0.035*
H8AB	0.797902	0.285254	0.212484	0.035*
H8AC	0.744610	0.276605	0.047211	0.035*
C8B	0.7311 (2)	0.25133 (5)	0.71549 (17)	0.0253 (3)
H8BA	0.804024	0.228079	0.702619	0.038*
H8BB	0.623525	0.247220	0.643615	0.038*
H8BC	0.725716	0.247811	0.808847	0.038*
C9B	0.95556 (19)	0.30328 (6)	0.80101 (17)	0.0262 (3)
H9BA	1.023075	0.278685	0.786654	0.039*
H9BB	0.957896	0.301826	0.897363	0.039*
H9BC	0.996504	0.333277	0.785234	0.039*
C9A	0.4339 (2)	0.27182 (5)	−0.01324 (16)	0.0250 (3)
H9AA	0.423761	0.239111	0.006049	0.037*
H9AB	0.461344	0.274795	−0.097116	0.037*
H9AC	0.331658	0.287521	−0.029048	0.037*
C10A	0.31633 (17)	0.39211 (5)	0.43994 (15)	0.0171 (3)
H10A	0.378049	0.365519	0.493885	0.021*
H10B	0.371412	0.420589	0.486577	0.021*
C10B	0.75399 (18)	0.43933 (5)	0.35454 (15)	0.0171 (3)
H10C	0.864527	0.432258	0.360219	0.021*
H10D	0.679970	0.417785	0.285938	0.021*
C11A	0.16618 (19)	0.39812 (5)	0.58899 (16)	0.0221 (3)
H11A	0.212623	0.428541	0.621570	0.033*
H11B	0.235138	0.374210	0.649046	0.033*
H11C	0.058738	0.396269	0.593469	0.033*
C11B	0.54322 (19)	0.49610 (6)	0.26906 (18)	0.0268 (3)
H11D	0.519831	0.528037	0.236702	0.040*
H11E	0.516980	0.491570	0.353053	0.040*
H11F	0.478442	0.475103	0.194836	0.040*
C12A	0.0765 (2)	0.34683 (5)	0.39286 (17)	0.0234 (3)
H12A	0.064020	0.342768	0.294375	0.035*
H12B	−0.029473	0.346212	0.400615	0.035*
H12C	0.142980	0.321831	0.449329	0.035*
C12B	0.7540 (2)	0.49281 (6)	0.17780 (18)	0.0283 (4)
H12D	0.726143	0.524235	0.141906	0.042*
H12E	0.693245	0.470638	0.105526	0.042*
H12F	0.869424	0.487744	0.202206	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Se1	0.01277 (8)	0.01188 (7)	0.01350 (8)	0.00028 (5)	0.00373 (6)	0.00024 (5)
N1A	0.0207 (7)	0.0164 (6)	0.0157 (6)	−0.0007 (5)	0.0045 (5)	−0.0028 (5)
N2A	0.0134 (6)	0.0167 (6)	0.0199 (6)	0.0000 (5)	0.0070 (5)	−0.0011 (5)
N1B	0.0201 (7)	0.0160 (6)	0.0175 (6)	0.0028 (5)	0.0061 (5)	0.0025 (5)
N2B	0.0184 (6)	0.0157 (6)	0.0230 (7)	0.0001 (5)	0.0072 (5)	0.0048 (5)
C1B	0.0099 (6)	0.0150 (6)	0.0145 (7)	0.0013 (5)	0.0019 (5)	−0.0010 (5)
C1A	0.0136 (7)	0.0115 (6)	0.0153 (7)	−0.0023 (5)	0.0026 (6)	0.0009 (5)
C2A	0.0183 (7)	0.0139 (6)	0.0171 (7)	−0.0036 (5)	0.0058 (6)	−0.0001 (5)
C2B	0.0110 (7)	0.0181 (7)	0.0167 (7)	0.0030 (5)	0.0043 (6)	0.0008 (5)
C3A	0.0234 (8)	0.0200 (7)	0.0131 (7)	−0.0039 (6)	0.0036 (6)	0.0017 (5)
C3B	0.0167 (7)	0.0227 (7)	0.0151 (7)	0.0039 (6)	0.0037 (6)	−0.0015 (6)
C4A	0.0177 (8)	0.0213 (7)	0.0197 (7)	−0.0008 (6)	0.0006 (6)	0.0059 (6)
C4B	0.0194 (8)	0.0199 (7)	0.0209 (8)	0.0007 (6)	0.0030 (6)	−0.0057 (6)
C5B	0.0158 (7)	0.0155 (7)	0.0238 (8)	0.0002 (6)	0.0044 (6)	−0.0004 (6)
C5A	0.0146 (7)	0.0178 (7)	0.0226 (8)	0.0003 (6)	0.0050 (6)	0.0024 (6)
C6B	0.0100 (7)	0.0156 (6)	0.0186 (7)	0.0021 (5)	0.0024 (6)	0.0005 (5)
C6A	0.0127 (7)	0.0139 (6)	0.0174 (7)	−0.0030 (5)	0.0035 (6)	0.0005 (5)
C7A	0.0221 (8)	0.0182 (7)	0.0142 (7)	−0.0026 (6)	0.0079 (6)	−0.0006 (5)
C7B	0.0180 (7)	0.0200 (7)	0.0147 (7)	0.0015 (6)	0.0073 (6)	0.0021 (5)
C8A	0.0269 (9)	0.0227 (8)	0.0202 (8)	0.0024 (6)	0.0076 (7)	−0.0029 (6)
C8B	0.0342 (10)	0.0184 (7)	0.0258 (8)	0.0010 (7)	0.0138 (7)	0.0028 (6)
C9B	0.0220 (8)	0.0270 (8)	0.0253 (8)	0.0065 (6)	0.0036 (7)	0.0034 (7)
C9A	0.0263 (9)	0.0247 (8)	0.0210 (8)	−0.0043 (7)	0.0053 (7)	−0.0071 (6)
C10A	0.0129 (7)	0.0203 (7)	0.0175 (7)	0.0002 (5)	0.0048 (6)	0.0000 (6)
C10B	0.0171 (7)	0.0143 (6)	0.0195 (7)	−0.0003 (5)	0.0062 (6)	0.0016 (5)
C11A	0.0203 (8)	0.0257 (8)	0.0229 (8)	0.0025 (6)	0.0110 (7)	−0.0006 (6)
C11B	0.0216 (8)	0.0243 (8)	0.0318 (9)	0.0056 (6)	0.0065 (7)	0.0066 (7)
C12A	0.0238 (8)	0.0198 (7)	0.0283 (9)	−0.0057 (6)	0.0118 (7)	−0.0021 (6)
C12B	0.0343 (10)	0.0238 (8)	0.0294 (9)	−0.0014 (7)	0.0148 (8)	0.0077 (7)

Geometric parameters (Å, º)

Se1—C1A	1.9440 (14)	C5A—H5AA	0.9500
Se1—C1B	1.9468 (13)	C6B—C10B	1.5170 (19)
Se1—N1B	3.0969 (12)	C6A—C10A	1.5164 (19)
Se1—N1A	3.1796 (12)	C7A—H7AA	0.9900
N1A—C8A	1.457 (2)	C7A—H7AB	0.9900
N1A—C9A	1.4612 (19)	C7B—H7BA	0.9900
N1A—C7A	1.4683 (17)	C7B—H7BB	0.9900
N2A—C11A	1.4626 (18)	C8A—H8AA	0.9800
N2A—C12A	1.4640 (18)	C8A—H8AB	0.9800
N2A—C10A	1.4650 (17)	C8A—H8AC	0.9800
N1B—C9B	1.457 (2)	C8B—H8BA	0.9800
N1B—C8B	1.4640 (19)	C8B—H8BB	0.9800
N1B—C7B	1.4662 (18)	C8B—H8BC	0.9800
N2B—C11B	1.461 (2)	C9B—H9BA	0.9800
N2B—C12B	1.4619 (19)	C9B—H9BB	0.9800
N2B—C10B	1.4653 (17)	C9B—H9BC	0.9800
C1B—C6B	1.4065 (19)	C9A—H9AA	0.9800
C1B—C2B	1.4108 (19)	C9A—H9AB	0.9800
C1A—C6A	1.4029 (19)	C9A—H9AC	0.9800
C1A—C2A	1.4124 (19)	C10A—H10A	0.9900
C2A—C3A	1.389 (2)	C10A—H10B	0.9900
C2A—C7A	1.513 (2)	C10B—H10C	0.9900
C2B—C3B	1.391 (2)	C10B—H10D	0.9900
C2B—C7B	1.5102 (19)	C11A—H11A	0.9800
C3A—C4A	1.390 (2)	C11A—H11B	0.9800
C3A—H3AA	0.9500	C11A—H11C	0.9800
C3B—C4B	1.390 (2)	C11B—H11D	0.9800
C3B—H3BA	0.9500	C11B—H11E	0.9800
C4A—C5A	1.386 (2)	C11B—H11F	0.9800
C4A—H4AA	0.9500	C12A—H12A	0.9800
C4B—C5B	1.385 (2)	C12A—H12B	0.9800
C4B—H4BA	0.9500	C12A—H12C	0.9800
C5B—C6B	1.402 (2)	C12B—H12D	0.9800
C5B—H5BA	0.9500	C12B—H12E	0.9800
C5A—C6A	1.398 (2)	C12B—H12F	0.9800
C1A—Se1—C1B	99.61 (6)	N1B—C7B—C2B	111.77 (11)
C1A—Se1—N1B	153.08 (5)	N1B—C7B—H7BA	109.3
C1B—Se1—N1B	71.09 (5)	C2B—C7B—H7BA	109.3
C1A—Se1—N1A	70.44 (5)	N1B—C7B—H7BB	109.3
C1B—Se1—N1A	149.78 (5)	C2B—C7B—H7BB	109.3
N1B—Se1—N1A	129.62 (3)	H7BA—C7B—H7BB	107.9
C8A—N1A—C9A	110.97 (12)	N1A—C8A—H8AA	109.5
C8A—N1A—C7A	111.29 (12)	N1A—C8A—H8AB	109.5
C9A—N1A—C7A	110.56 (12)	H8AA—C8A—H8AB	109.5
C8A—N1A—Se1	102.06 (8)	N1A—C8A—H8AC	109.5
C9A—N1A—Se1	141.15 (9)	H8AA—C8A—H8AC	109.5
C7A—N1A—Se1	73.92 (7)	H8AB—C8A—H8AC	109.5
C11A—N2A—C12A	109.40 (11)	N1B—C8B—H8BA	109.5
C11A—N2A—C10A	108.84 (11)	N1B—C8B—H8BB	109.5
C12A—N2A—C10A	110.54 (11)	H8BA—C8B—H8BB	109.5
C9B—N1B—C8B	110.72 (12)	N1B—C8B—H8BC	109.5
C9B—N1B—C7B	111.22 (12)	H8BA—C8B—H8BC	109.5
C8B—N1B—C7B	110.26 (12)	H8BB—C8B—H8BC	109.5
C9B—N1B—Se1	130.41 (9)	N1B—C9B—H9BA	109.5
C8B—N1B—Se1	111.52 (9)	N1B—C9B—H9BB	109.5
C7B—N1B—Se1	76.59 (7)	H9BA—C9B—H9BB	109.5
C11B—N2B—C12B	109.95 (13)	N1B—C9B—H9BC	109.5
C11B—N2B—C10B	111.02 (11)	H9BA—C9B—H9BC	109.5
C12B—N2B—C10B	109.02 (11)	H9BB—C9B—H9BC	109.5
C6B—C1B—C2B	120.50 (12)	N1A—C9A—H9AA	109.5
C6B—C1B—Se1	122.43 (10)	N1A—C9A—H9AB	109.5
C2B—C1B—Se1	117.02 (10)	H9AA—C9A—H9AB	109.5
C6A—C1A—C2A	120.47 (13)	N1A—C9A—H9AC	109.5
C6A—C1A—Se1	121.85 (10)	H9AA—C9A—H9AC	109.5
C2A—C1A—Se1	117.63 (10)	H9AB—C9A—H9AC	109.5
C3A—C2A—C1A	119.17 (13)	N2A—C10A—C6A	113.42 (12)
C3A—C2A—C7A	120.29 (13)	N2A—C10A—H10A	108.9
C1A—C2A—C7A	120.54 (13)	C6A—C10A—H10A	108.9
C3B—C2B—C1B	119.04 (13)	N2A—C10A—H10B	108.9
C3B—C2B—C7B	120.01 (13)	C6A—C10A—H10B	108.9
C1B—C2B—C7B	120.94 (12)	H10A—C10A—H10B	107.7
C2A—C3A—C4A	120.82 (13)	N2B—C10B—C6B	113.86 (11)
C2A—C3A—H3AA	119.6	N2B—C10B—H10C	108.8
C4A—C3A—H3AA	119.6	C6B—C10B—H10C	108.8
C4B—C3B—C2B	120.85 (13)	N2B—C10B—H10D	108.8
C4B—C3B—H3BA	119.6	C6B—C10B—H10D	108.8
C2B—C3B—H3BA	119.6	H10C—C10B—H10D	107.7
C5A—C4A—C3A	119.62 (14)	N2A—C11A—H11A	109.5
C5A—C4A—H4AA	120.2	N2A—C11A—H11B	109.5
C3A—C4A—H4AA	120.2	H11A—C11A—H11B	109.5
C5B—C4B—C3B	119.79 (13)	N2A—C11A—H11C	109.5
C5B—C4B—H4BA	120.1	H11A—C11A—H11C	109.5
C3B—C4B—H4BA	120.1	H11B—C11A—H11C	109.5
C4B—C5B—C6B	121.18 (13)	N2B—C11B—H11D	109.5
C4B—C5B—H5BA	119.4	N2B—C11B—H11E	109.5
C6B—C5B—H5BA	119.4	H11D—C11B—H11E	109.5
C4A—C5A—C6A	121.36 (14)	N2B—C11B—H11F	109.5
C4A—C5A—H5AA	119.3	H11D—C11B—H11F	109.5
C6A—C5A—H5AA	119.3	H11E—C11B—H11F	109.5
C5B—C6B—C1B	118.43 (13)	N2A—C12A—H12A	109.5
C5B—C6B—C10B	118.49 (12)	N2A—C12A—H12B	109.5
C1B—C6B—C10B	122.81 (12)	H12A—C12A—H12B	109.5
C5A—C6A—C1A	118.53 (13)	N2A—C12A—H12C	109.5
C5A—C6A—C10A	119.08 (12)	H12A—C12A—H12C	109.5
C1A—C6A—C10A	122.39 (12)	H12B—C12A—H12C	109.5
N1A—C7A—C2A	111.24 (11)	N2B—C12B—H12D	109.5
N1A—C7A—H7AA	109.4	N2B—C12B—H12E	109.5
C2A—C7A—H7AA	109.4	H12D—C12B—H12E	109.5
N1A—C7A—H7AB	109.4	N2B—C12B—H12F	109.5
C2A—C7A—H7AB	109.4	H12D—C12B—H12F	109.5
H7AA—C7A—H7AB	108.0	H12E—C12B—H12F	109.5
C6A—C1A—C2A—C3A	0.9 (2)	C4A—C5A—C6A—C10A	−179.22 (13)
Se1—C1A—C2A—C3A	178.23 (10)	C2A—C1A—C6A—C5A	−1.6 (2)
C6A—C1A—C2A—C7A	−178.59 (12)	Se1—C1A—C6A—C5A	−178.83 (10)
Se1—C1A—C2A—C7A	−1.25 (17)	C2A—C1A—C6A—C10A	178.70 (12)
C6B—C1B—C2B—C3B	4.6 (2)	Se1—C1A—C6A—C10A	1.47 (18)
Se1—C1B—C2B—C3B	−178.10 (10)	C8A—N1A—C7A—C2A	−157.07 (12)
C6B—C1B—C2B—C7B	−174.40 (13)	C9A—N1A—C7A—C2A	79.13 (15)
Se1—C1B—C2B—C7B	2.88 (17)	Se1—N1A—C7A—C2A	−60.12 (10)
C1A—C2A—C3A—C4A	0.4 (2)	C3A—C2A—C7A—N1A	−111.26 (15)
C7A—C2A—C3A—C4A	179.89 (13)	C1A—C2A—C7A—N1A	68.21 (17)
C1B—C2B—C3B—C4B	−0.9 (2)	C9B—N1B—C7B—C2B	70.47 (15)
C7B—C2B—C3B—C4B	178.13 (13)	C8B—N1B—C7B—C2B	−166.31 (12)
C2A—C3A—C4A—C5A	−1.0 (2)	Se1—N1B—C7B—C2B	−58.01 (10)
C2B—C3B—C4B—C5B	−2.4 (2)	C3B—C2B—C7B—N1B	−117.48 (14)
C3B—C4B—C5B—C6B	2.0 (2)	C1B—C2B—C7B—N1B	61.53 (17)
C3A—C4A—C5A—C6A	0.2 (2)	C11A—N2A—C10A—C6A	−173.77 (11)
C4B—C5B—C6B—C1B	1.7 (2)	C12A—N2A—C10A—C6A	66.06 (15)
C4B—C5B—C6B—C10B	−172.60 (13)	C5A—C6A—C10A—N2A	32.96 (17)
C2B—C1B—C6B—C5B	−5.0 (2)	C1A—C6A—C10A—N2A	−147.35 (13)
Se1—C1B—C6B—C5B	177.90 (10)	C11B—N2B—C10B—C6B	−68.42 (16)
C2B—C1B—C6B—C10B	169.02 (13)	C12B—N2B—C10B—C6B	170.30 (13)
Se1—C1B—C6B—C10B	−8.11 (19)	C5B—C6B—C10B—N2B	−38.24 (18)
C4A—C5A—C6A—C1A	1.1 (2)	C1B—C6B—C10B—N2B	147.78 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10A—H10A···Se1	0.99	2.75	3.2623 (14)	113
C10B—H10D···Se1	0.99	2.77	3.2992 (14)	114
C11A—H11A···N2B^i	0.98	2.59	3.563 (2)	170

Symmetry code: (i) −x+1, −y+1, −z+1.

{µ-2,2'-Bis[(dimethylamino)methyl]-4,4'-bis[(dimethylazaniumyl)methyl]-3,3'-selanediyldiphenyl-κ⁴C¹,N²:C^1',N^2'}bis[dichloridopalladium(II)] (15)

Crystal data

[Pd2Cl4(C24H38N4Se)]	F(000) = 3232
Mr = 816.14	Dx = 1.365 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 21.422 (1) Å	Cell parameters from 9802 reflections
b = 21.8012 (10) Å	θ = 2.8–28.4°
c = 19.1405 (10) Å	µ = 2.11 mm^−1
β = 117.290 (2)°	T = 100 K
V = 7944.1 (7) Å^3	Plate, brown
Z = 8	0.26 × 0.25 × 0.08 mm

Data collection

Bruker Quest diffractometer	7722 reflections with I > 2σ(I)
ω scans	Rint = 0.032
Absorption correction: analytical (APEX2; Bruker, 2005)	θmax = 28.4°, θmin = 2.3°
Tmin = 0.583, Tmax = 0.945	h = −24→28
27098 measured reflections	k = −28→29
9460 independent reflections	l = −25→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: mixed
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0185P)^2 + 71.8262P] where P = (Fo^2 + 2Fc^2)/3
9460 reflections	(Δ/σ)max = 0.001
331 parameters	Δρmax = 1.16 e Å^−3
2 restraints	Δρmin = −1.42 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
Pd1	0.59869 (2)	−0.05743 (2)	0.47261 (2)	0.02383 (8)
Se1A	0.500000	0.13801 (2)	0.250000	0.02063 (11)
Cl1A	0.70577 (5)	−0.10481 (5)	0.57390 (7)	0.0323 (2)
Cl2A	0.53094 (6)	−0.13521 (5)	0.48594 (7)	0.0312 (2)
N1A	0.65190 (17)	0.01586 (17)	0.4525 (2)	0.0272 (7)
N2A	0.3529 (2)	0.17182 (16)	0.3198 (2)	0.0281 (7)
H2AA	0.355 (3)	0.155 (2)	0.360 (2)	0.034*
C1A	0.5154 (2)	−0.01040 (18)	0.3988 (2)	0.0239 (8)
C2A	0.53077 (19)	0.03635 (18)	0.3577 (2)	0.0209 (7)
C3A	0.47963 (19)	0.07845 (17)	0.3118 (2)	0.0196 (7)
C4A	0.4125 (2)	0.07638 (17)	0.3079 (2)	0.0222 (7)
C5A	0.3978 (2)	0.02871 (19)	0.3474 (3)	0.0259 (8)
H5AA	0.352097	0.025675	0.343721	0.031*
C6A	0.4488 (2)	−0.01430 (18)	0.3920 (2)	0.0246 (8)
H6AA	0.437470	−0.046410	0.417798	0.030*
C7A	0.6051 (2)	0.03783 (19)	0.3702 (2)	0.0250 (8)
H7AA	0.618135	0.080105	0.363158	0.030*
H7AB	0.610287	0.010865	0.331533	0.030*
C8A	0.7218 (2)	0.0007 (2)	0.4597 (3)	0.0363 (10)
H8AA	0.741351	0.036865	0.446197	0.054*
H8AB	0.717354	−0.032920	0.423737	0.054*
H8AC	0.753133	−0.011730	0.513803	0.054*
C9A	0.6592 (2)	0.0657 (2)	0.5083 (3)	0.0307 (9)
H9AA	0.685427	0.099871	0.500995	0.046*
H9AB	0.684597	0.050340	0.562271	0.046*
H9AC	0.612541	0.079953	0.498530	0.046*
C10A	0.3549 (2)	0.12247 (18)	0.2652 (3)	0.0255 (8)
H10A	0.309085	0.100995	0.240662	0.031*
H10B	0.362263	0.141788	0.222794	0.031*
C11A	0.4123 (3)	0.2147 (2)	0.3443 (3)	0.0344 (10)
H11A	0.408696	0.246081	0.378889	0.052*
H11B	0.411350	0.234373	0.297753	0.052*
H11C	0.456550	0.192181	0.372523	0.052*
C12A	0.2843 (3)	0.2052 (2)	0.2814 (3)	0.0360 (10)
H12A	0.285099	0.239686	0.314641	0.054*
H12B	0.246135	0.177171	0.274191	0.054*
H12C	0.276868	0.220772	0.230046	0.054*
Pd2	0.41782 (2)	0.42261 (2)	0.36778 (2)	0.02558 (8)
Se1B	0.500000	0.63190 (3)	0.250000	0.02969 (14)
Cl1B	0.31592 (6)	0.36455 (5)	0.35503 (8)	0.0411 (3)
Cl2B	0.49272 (6)	0.35269 (5)	0.45935 (7)	0.0351 (2)
N1B	0.35807 (19)	0.48686 (18)	0.2830 (2)	0.0315 (8)
N2B	0.6116 (2)	0.68782 (16)	0.4641 (2)	0.0304 (8)
H2BA	0.604 (3)	0.673 (2)	0.502 (2)	0.036*
C1B	0.4936 (2)	0.48115 (18)	0.3851 (2)	0.0225 (8)
C2B	0.4763 (2)	0.52518 (18)	0.3253 (2)	0.0235 (8)
C3B	0.5216 (2)	0.57438 (17)	0.3352 (2)	0.0231 (8)
C4B	0.5827 (2)	0.58241 (18)	0.4057 (3)	0.0239 (8)
C5B	0.5988 (2)	0.53807 (18)	0.4644 (3)	0.0241 (8)
H5BA	0.640374	0.542458	0.512653	0.029*
C6B	0.5556 (2)	0.48803 (18)	0.4539 (2)	0.0247 (8)
H6BA	0.568680	0.458108	0.494252	0.030*
C7B	0.4060 (2)	0.51609 (18)	0.2548 (2)	0.0244 (8)
H7BA	0.386657	0.556024	0.229534	0.029*
H7BB	0.410910	0.489269	0.215832	0.029*
C8B	0.2969 (3)	0.4609 (3)	0.2132 (3)	0.0446 (13)
H8BA	0.274262	0.493397	0.174272	0.067*
H8BB	0.263130	0.444042	0.229451	0.067*
H8BC	0.312954	0.428325	0.190100	0.067*
C9B	0.3337 (3)	0.5340 (2)	0.3192 (3)	0.0404 (11)
H9BA	0.304542	0.563822	0.279202	0.061*
H9BB	0.374304	0.554999	0.360553	0.061*
H9BC	0.305988	0.514808	0.342168	0.061*
C10B	0.6315 (2)	0.63673 (19)	0.4247 (3)	0.0290 (9)
H10C	0.630372	0.652421	0.375547	0.035*
H10D	0.680164	0.623311	0.459777	0.035*
C11B	0.5438 (3)	0.71755 (19)	0.4100 (3)	0.0335 (10)
H11D	0.532117	0.749038	0.438596	0.050*
H11E	0.506512	0.686577	0.389673	0.050*
H11F	0.548222	0.736560	0.366039	0.050*
C12B	0.6685 (3)	0.7345 (2)	0.4960 (3)	0.0468 (13)
H12D	0.653409	0.769171	0.517165	0.070*
H12E	0.678865	0.748950	0.453945	0.070*
H12F	0.710857	0.716118	0.538035	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pd1	0.02879 (15)	0.02520 (15)	0.02320 (15)	0.00442 (12)	0.01682 (12)	0.00370 (11)
Se1A	0.0233 (2)	0.0222 (2)	0.0186 (3)	0.000	0.0115 (2)	0.000
Cl1A	0.0318 (5)	0.0365 (5)	0.0353 (6)	0.0103 (4)	0.0210 (4)	0.0116 (4)
Cl2A	0.0396 (5)	0.0223 (5)	0.0349 (6)	−0.0017 (4)	0.0199 (5)	−0.0002 (4)
N1A	0.0226 (16)	0.0366 (19)	0.0262 (18)	0.0046 (14)	0.0146 (14)	0.0097 (15)
N2A	0.0377 (19)	0.0268 (17)	0.0278 (19)	0.0039 (15)	0.0219 (16)	−0.0020 (14)
C1A	0.032 (2)	0.0251 (19)	0.0182 (18)	0.0018 (16)	0.0145 (16)	−0.0020 (14)
C2A	0.0166 (16)	0.0287 (19)	0.0183 (18)	0.0011 (14)	0.0090 (14)	−0.0018 (14)
C3A	0.0224 (17)	0.0243 (18)	0.0160 (17)	−0.0008 (14)	0.0121 (14)	−0.0021 (14)
C4A	0.0249 (18)	0.0223 (18)	0.0214 (19)	0.0010 (14)	0.0122 (15)	−0.0027 (14)
C5A	0.0275 (19)	0.029 (2)	0.030 (2)	−0.0029 (16)	0.0205 (17)	−0.0051 (16)
C6A	0.030 (2)	0.0226 (18)	0.027 (2)	0.0015 (15)	0.0188 (17)	−0.0018 (15)
C7A	0.0237 (18)	0.030 (2)	0.025 (2)	0.0044 (15)	0.0139 (16)	0.0086 (16)
C8A	0.028 (2)	0.045 (3)	0.043 (3)	0.0093 (19)	0.022 (2)	0.015 (2)
C9A	0.026 (2)	0.037 (2)	0.025 (2)	−0.0061 (17)	0.0081 (17)	0.0024 (17)
C10A	0.0255 (19)	0.0265 (19)	0.028 (2)	0.0017 (15)	0.0155 (17)	−0.0044 (16)
C11A	0.046 (3)	0.026 (2)	0.032 (2)	−0.0029 (19)	0.018 (2)	−0.0044 (17)
C12A	0.043 (3)	0.029 (2)	0.043 (3)	0.0129 (19)	0.026 (2)	0.0057 (19)
Pd2	0.03141 (16)	0.02333 (15)	0.02325 (16)	−0.00183 (12)	0.01361 (13)	0.00145 (11)
Se1B	0.0537 (4)	0.0189 (3)	0.0227 (3)	0.000	0.0229 (3)	0.000
Cl1B	0.0407 (6)	0.0351 (6)	0.0427 (7)	−0.0112 (5)	0.0150 (5)	0.0053 (5)
Cl2B	0.0445 (6)	0.0246 (5)	0.0376 (6)	0.0045 (4)	0.0199 (5)	0.0078 (4)
N1B	0.0283 (18)	0.038 (2)	0.0274 (19)	−0.0010 (15)	0.0118 (15)	0.0065 (15)
N2B	0.040 (2)	0.0223 (17)	0.032 (2)	−0.0089 (15)	0.0190 (17)	0.0008 (14)
C1B	0.0271 (19)	0.0238 (18)	0.0207 (19)	0.0001 (15)	0.0145 (16)	−0.0027 (14)
C2B	0.032 (2)	0.0235 (18)	0.0203 (18)	0.0045 (15)	0.0162 (16)	−0.0011 (14)
C3B	0.034 (2)	0.0192 (17)	0.025 (2)	0.0038 (15)	0.0221 (17)	−0.0011 (14)
C4B	0.0295 (19)	0.0222 (18)	0.031 (2)	0.0006 (15)	0.0232 (17)	−0.0009 (15)
C5B	0.0264 (19)	0.0222 (18)	0.029 (2)	0.0060 (15)	0.0170 (17)	0.0033 (15)
C6B	0.0291 (19)	0.0236 (19)	0.024 (2)	0.0039 (15)	0.0146 (16)	0.0005 (15)
C7B	0.031 (2)	0.0269 (19)	0.0172 (18)	−0.0021 (16)	0.0126 (16)	0.0036 (15)
C8B	0.035 (2)	0.057 (3)	0.034 (3)	−0.007 (2)	0.009 (2)	0.011 (2)
C9B	0.041 (3)	0.045 (3)	0.044 (3)	0.018 (2)	0.028 (2)	0.017 (2)
C10B	0.032 (2)	0.030 (2)	0.034 (2)	−0.0037 (17)	0.0233 (19)	−0.0003 (17)
C11B	0.048 (3)	0.023 (2)	0.035 (2)	−0.0021 (18)	0.023 (2)	−0.0060 (17)
C12B	0.055 (3)	0.039 (3)	0.042 (3)	−0.024 (2)	0.019 (3)	−0.004 (2)

Geometric parameters (Å, º)

Pd1—C1A	1.980 (4)	Pd2—C1B	1.969 (4)
Pd1—N1A	2.098 (4)	Pd2—N1B	2.081 (4)
Pd1—Cl2A	2.3209 (11)	Pd2—Cl2B	2.3220 (11)
Pd1—Cl1A	2.4515 (11)	Pd2—Cl1B	2.4368 (12)
Se1A—C3A	1.936 (4)	Se1B—C3B^i	1.937 (4)
Se1A—C3A^i	1.936 (4)	Se1B—C3B	1.938 (4)
N1A—C8A	1.477 (5)	N1B—C9B	1.464 (6)
N1A—C9A	1.481 (6)	N1B—C8B	1.488 (6)
N1A—C7A	1.506 (5)	N1B—C7B	1.504 (5)
N2A—C11A	1.472 (6)	N2B—C12B	1.488 (6)
N2A—C12A	1.497 (6)	N2B—C11B	1.491 (6)
N2A—C10A	1.513 (5)	N2B—C10B	1.512 (6)
N2A—H2AA	0.836 (19)	N2B—H2BA	0.860 (19)
C1A—C6A	1.374 (6)	C1B—C6B	1.384 (5)
C1A—C2A	1.415 (6)	C1B—C2B	1.408 (6)
C2A—C3A	1.390 (5)	C2B—C3B	1.399 (6)
C2A—C7A	1.498 (5)	C2B—C7B	1.505 (5)
C3A—C4A	1.406 (5)	C3B—C4B	1.394 (6)
C4A—C5A	1.404 (6)	C4B—C5B	1.400 (6)
C4A—C10A	1.509 (5)	C4B—C10B	1.510 (6)
C5A—C6A	1.395 (6)	C5B—C6B	1.384 (6)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—H6AA	0.9500	C6B—H6BA	0.9500
C7A—H7AA	0.9900	C7B—H7BA	0.9900
C7A—H7AB	0.9900	C7B—H7BB	0.9900
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800
C10A—H10A	0.9900	C10B—H10C	0.9900
C10A—H10B	0.9900	C10B—H10D	0.9900
C11A—H11A	0.9800	C11B—H11D	0.9800
C11A—H11B	0.9800	C11B—H11E	0.9800
C11A—H11C	0.9800	C11B—H11F	0.9800
C12A—H12A	0.9800	C12B—H12D	0.9800
C12A—H12B	0.9800	C12B—H12E	0.9800
C12A—H12C	0.9800	C12B—H12F	0.9800
C1A—Pd1—N1A	82.10 (15)	C1B—Pd2—N1B	81.94 (15)
C1A—Pd1—Cl2A	93.00 (12)	C1B—Pd2—Cl2B	93.86 (12)
N1A—Pd1—Cl2A	175.02 (10)	N1B—Pd2—Cl2B	174.73 (11)
C1A—Pd1—Cl1A	173.22 (12)	C1B—Pd2—Cl1B	169.92 (12)
N1A—Pd1—Cl1A	94.35 (9)	N1B—Pd2—Cl1B	93.97 (11)
Cl2A—Pd1—Cl1A	90.62 (4)	Cl2B—Pd2—Cl1B	90.68 (4)
C3A—Se1A—C3A^i	95.8 (2)	C3B^i—Se1B—C3B	99.3 (2)
C8A—N1A—C9A	109.2 (4)	C9B—N1B—C8B	109.4 (4)
C8A—N1A—C7A	109.2 (3)	C9B—N1B—C7B	108.9 (4)
C9A—N1A—C7A	108.7 (3)	C8B—N1B—C7B	107.8 (4)
C8A—N1A—Pd1	115.2 (3)	C9B—N1B—Pd2	109.2 (3)
C9A—N1A—Pd1	108.3 (3)	C8B—N1B—Pd2	114.7 (3)
C7A—N1A—Pd1	106.1 (2)	C7B—N1B—Pd2	106.7 (2)
C11A—N2A—C12A	111.0 (3)	C12B—N2B—C11B	110.0 (4)
C11A—N2A—C10A	112.2 (3)	C12B—N2B—C10B	110.1 (4)
C12A—N2A—C10A	109.8 (3)	C11B—N2B—C10B	112.4 (4)
C11A—N2A—H2AA	108 (4)	C12B—N2B—H2BA	109 (4)
C12A—N2A—H2AA	107 (4)	C11B—N2B—H2BA	104 (4)
C10A—N2A—H2AA	109 (4)	C10B—N2B—H2BA	110 (4)
C6A—C1A—C2A	119.2 (4)	C6B—C1B—C2B	118.6 (4)
C6A—C1A—Pd1	126.3 (3)	C6B—C1B—Pd2	126.0 (3)
C2A—C1A—Pd1	113.9 (3)	C2B—C1B—Pd2	114.6 (3)
C3A—C2A—C1A	120.6 (3)	C3B—C2B—C1B	120.3 (4)
C3A—C2A—C7A	123.9 (3)	C3B—C2B—C7B	124.7 (4)
C1A—C2A—C7A	115.4 (3)	C1B—C2B—C7B	114.9 (4)
C2A—C3A—C4A	120.2 (3)	C4B—C3B—C2B	120.8 (4)
C2A—C3A—Se1A	119.7 (3)	C4B—C3B—Se1B	119.3 (3)
C4A—C3A—Se1A	120.1 (3)	C2B—C3B—Se1B	119.9 (3)
C5A—C4A—C3A	118.2 (4)	C3B—C4B—C5B	117.8 (4)
C5A—C4A—C10A	117.0 (4)	C3B—C4B—C10B	124.8 (4)
C3A—C4A—C10A	124.8 (4)	C5B—C4B—C10B	117.4 (4)
C6A—C5A—C4A	121.3 (4)	C6B—C5B—C4B	121.7 (4)
C6A—C5A—H5AA	119.3	C6B—C5B—H5BA	119.1
C4A—C5A—H5AA	119.3	C4B—C5B—H5BA	119.1
C1A—C6A—C5A	120.3 (4)	C5B—C6B—C1B	120.6 (4)
C1A—C6A—H6AA	119.9	C5B—C6B—H6BA	119.7
C5A—C6A—H6AA	119.9	C1B—C6B—H6BA	119.7
C2A—C7A—N1A	108.0 (3)	N1B—C7B—C2B	107.6 (3)
C2A—C7A—H7AA	110.1	N1B—C7B—H7BA	110.2
N1A—C7A—H7AA	110.1	C2B—C7B—H7BA	110.2
C2A—C7A—H7AB	110.1	N1B—C7B—H7BB	110.2
N1A—C7A—H7AB	110.1	C2B—C7B—H7BB	110.2
H7AA—C7A—H7AB	108.4	H7BA—C7B—H7BB	108.5
N1A—C8A—H8AA	109.5	N1B—C8B—H8BA	109.5
N1A—C8A—H8AB	109.5	N1B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
N1A—C8A—H8AC	109.5	N1B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5
N1A—C9A—H9AA	109.5	N1B—C9B—H9BA	109.5
N1A—C9A—H9AB	109.5	N1B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
N1A—C9A—H9AC	109.5	N1B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
C4A—C10A—N2A	112.0 (3)	C4B—C10B—N2B	112.0 (3)
C4A—C10A—H10A	109.2	C4B—C10B—H10C	109.2
N2A—C10A—H10A	109.2	N2B—C10B—H10C	109.2
C4A—C10A—H10B	109.2	C4B—C10B—H10D	109.2
N2A—C10A—H10B	109.2	N2B—C10B—H10D	109.2
H10A—C10A—H10B	107.9	H10C—C10B—H10D	107.9
N2A—C11A—H11A	109.5	N2B—C11B—H11D	109.5
N2A—C11A—H11B	109.5	N2B—C11B—H11E	109.5
H11A—C11A—H11B	109.5	H11D—C11B—H11E	109.5
N2A—C11A—H11C	109.5	N2B—C11B—H11F	109.5
H11A—C11A—H11C	109.5	H11D—C11B—H11F	109.5
H11B—C11A—H11C	109.5	H11E—C11B—H11F	109.5
N2A—C12A—H12A	109.5	N2B—C12B—H12D	109.5
N2A—C12A—H12B	109.5	N2B—C12B—H12E	109.5
H12A—C12A—H12B	109.5	H12D—C12B—H12E	109.5
N2A—C12A—H12C	109.5	N2B—C12B—H12F	109.5
H12A—C12A—H12C	109.5	H12D—C12B—H12F	109.5
H12B—C12A—H12C	109.5	H12E—C12B—H12F	109.5
C6A—C1A—C2A—C3A	0.8 (6)	C6B—C1B—C2B—C3B	0.6 (6)
Pd1—C1A—C2A—C3A	−171.4 (3)	Pd2—C1B—C2B—C3B	171.2 (3)
C6A—C1A—C2A—C7A	178.7 (4)	C6B—C1B—C2B—C7B	−176.5 (3)
Pd1—C1A—C2A—C7A	6.4 (5)	Pd2—C1B—C2B—C7B	−5.9 (4)
C1A—C2A—C3A—C4A	2.4 (6)	C1B—C2B—C3B—C4B	−3.1 (6)
C7A—C2A—C3A—C4A	−175.3 (4)	C7B—C2B—C3B—C4B	173.7 (4)
C1A—C2A—C3A—Se1A	−175.3 (3)	C1B—C2B—C3B—Se1B	176.3 (3)
C7A—C2A—C3A—Se1A	7.0 (5)	C7B—C2B—C3B—Se1B	−6.8 (5)
C2A—C3A—C4A—C5A	−3.9 (6)	C2B—C3B—C4B—C5B	3.0 (6)
Se1A—C3A—C4A—C5A	173.7 (3)	Se1B—C3B—C4B—C5B	−176.4 (3)
C2A—C3A—C4A—C10A	175.1 (4)	C2B—C3B—C4B—C10B	−174.5 (4)
Se1A—C3A—C4A—C10A	−7.3 (5)	Se1B—C3B—C4B—C10B	6.1 (5)
C3A—C4A—C5A—C6A	2.5 (6)	C3B—C4B—C5B—C6B	−0.6 (6)
C10A—C4A—C5A—C6A	−176.6 (4)	C10B—C4B—C5B—C6B	177.1 (4)
C2A—C1A—C6A—C5A	−2.3 (6)	C4B—C5B—C6B—C1B	−1.8 (6)
Pd1—C1A—C6A—C5A	168.9 (3)	C2B—C1B—C6B—C5B	1.8 (6)
C4A—C5A—C6A—C1A	0.6 (6)	Pd2—C1B—C6B—C5B	−167.6 (3)
C3A—C2A—C7A—N1A	145.8 (4)	C9B—N1B—C7B—C2B	78.0 (4)
C1A—C2A—C7A—N1A	−32.0 (5)	C8B—N1B—C7B—C2B	−163.4 (4)
C8A—N1A—C7A—C2A	164.8 (4)	Pd2—N1B—C7B—C2B	−39.7 (4)
C9A—N1A—C7A—C2A	−76.2 (4)	C3B—C2B—C7B—N1B	−145.9 (4)
Pd1—N1A—C7A—C2A	40.1 (4)	C1B—C2B—C7B—N1B	31.1 (5)
C5A—C4A—C10A—N2A	83.1 (4)	C3B—C4B—C10B—N2B	90.5 (5)
C3A—C4A—C10A—N2A	−95.9 (5)	C5B—C4B—C10B—N2B	−87.1 (5)
C11A—N2A—C10A—C4A	72.1 (4)	C12B—N2B—C10B—C4B	168.6 (4)
C12A—N2A—C10A—C4A	−164.0 (4)	C11B—N2B—C10B—C4B	−68.3 (5)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2AA···Cl1A^ii	0.84 (2)	2.45 (3)	3.194 (4)	149 (5)
N2A—H2AA···Cl2A^ii	0.84 (2)	2.87 (4)	3.488 (4)	132 (4)
C8A—H8AC···Cl1A	0.98	2.75	3.299 (5)	116
C10A—H10B···Se1A	0.99	2.75	3.270 (4)	113
C11A—H11A···Cl2B	0.98	2.91	3.659 (4)	134
C11A—H11C···Cl2A^ii	0.98	2.88	3.379 (5)	113
C12A—H12A···Cl1B	0.98	2.82	3.692 (5)	148
N2B—H2BA···Cl1B^iii	0.86 (2)	2.61 (4)	3.282 (4)	135 (4)
N2B—H2BA···Cl2B^iii	0.86 (2)	2.58 (3)	3.306 (4)	143 (4)
C8B—H8BB···Cl1B	0.98	2.75	3.306 (5)	117
C10B—H10C···Se1B	0.99	2.76	3.239 (5)	110
C10B—H10D···Cl1A^iv	0.99	2.83	3.542 (4)	130
C11B—H11D···Cl2A^v	0.98	2.69	3.587 (4)	153
C12B—H12D···Cl1A^v	0.98	2.98	3.747 (5)	136
C12B—H12F···Cl1B^iii	0.98	2.95	3.468 (6)	114

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, −y+1/2, −z+1; (v) x, y+1, z.

{µ-Bis{2,6-bis[(dimethylamino)methyl]benzeneselanolato-κ⁴N²,Se:Se,N⁶}-µ-chlorido-bis[chloridomercury(II)] (16)

Crystal data

[Hg2(C12H19N2Se)Cl3]	F(000) = 1400
Mr = 777.78	Dx = 2.861 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.4366 (12) Å	Cell parameters from 19623 reflections
b = 8.3635 (8) Å	θ = 2.7–33.2°
c = 18.9894 (19) Å	µ = 19.44 mm^−1
β = 96.230 (4)°	T = 100 K
V = 1805.6 (3) Å^3	Plate, colourless
Z = 4	0.18 × 0.15 × 0.08 mm

Data collection

Bruker Quest diffractometer	9995 reflections with I > 2σ(I)
ω scans	θmax = 33.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.307, Tmax = 0.746	k = 0→12
18121 measured reflections	l = 0→29
11191 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.169	H-atom parameters constrained
S = 1.17	w = 1/[σ^2(Fo^2) + 163.3856P] where P = (Fo^2 + 2Fc^2)/3
11191 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 4.41 e Å^−3
116 restraints	Δρmin = −4.77 e Å^−3

Special details

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. Refined as a 2-component twin

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

	x	y	z	Uiso*/Ueq
Hg1	0.58521 (5)	0.70850 (8)	0.74456 (3)	0.01472 (12)
Hg2	0.84222 (5)	0.71587 (8)	0.68071 (3)	0.01328 (12)
Se1	0.66670 (13)	0.53356 (18)	0.65169 (8)	0.0107 (3)
Cl1	0.6915 (4)	0.9731 (4)	0.68621 (19)	0.0142 (6)
Cl2	0.5438 (4)	0.8042 (6)	0.8563 (2)	0.0241 (9)
Cl3	1.0216 (3)	0.8054 (6)	0.7406 (2)	0.0212 (8)
N1	0.3935 (13)	0.7331 (18)	0.6769 (7)	0.016 (2)
N2	0.8741 (13)	0.7528 (15)	0.5567 (7)	0.014 (2)
C1	0.5960 (13)	0.6438 (18)	0.5680 (8)	0.012 (2)
C2	0.4735 (14)	0.6746 (19)	0.5606 (8)	0.013 (2)
C3	0.4235 (16)	0.7457 (18)	0.4981 (8)	0.016 (3)
H3A	0.341543	0.767683	0.492727	0.019*
C4	0.4893 (15)	0.786 (2)	0.4436 (8)	0.017 (3)
H4A	0.452749	0.833456	0.401436	0.020*
C5	0.6085 (18)	0.7550 (18)	0.4511 (8)	0.017 (3)
H5A	0.653682	0.783596	0.413854	0.020*
C6	0.6654 (14)	0.6819 (17)	0.5130 (7)	0.011 (2)
C7	0.3949 (13)	0.626 (2)	0.6149 (8)	0.014 (2)
H7A	0.313580	0.617772	0.591310	0.017*
H7B	0.418802	0.518194	0.632318	0.017*
C8	0.3049 (15)	0.671 (2)	0.7230 (10)	0.023 (3)
H8A	0.226532	0.672053	0.696356	0.035*
H8B	0.304750	0.739546	0.764916	0.035*
H8C	0.325503	0.561638	0.737843	0.035*
C9	0.3672 (18)	0.898 (2)	0.6557 (10)	0.023 (3)
H9A	0.287027	0.904118	0.631753	0.035*
H9B	0.423066	0.933740	0.623368	0.035*
H9C	0.373896	0.966432	0.697797	0.035*
C10	0.7933 (14)	0.641 (2)	0.5139 (8)	0.014 (2)
H10A	0.806222	0.531640	0.533047	0.017*
H10B	0.813806	0.640717	0.464600	0.017*
C11	0.8541 (17)	0.918 (2)	0.5332 (9)	0.019 (3)
H11A	0.864962	0.926067	0.482889	0.028*
H11B	0.910252	0.988082	0.560823	0.028*
H11C	0.773758	0.949458	0.540288	0.028*
C12	0.9964 (14)	0.706 (2)	0.5520 (9)	0.020 (3)
H12A	1.017901	0.732188	0.504762	0.029*
H12B	1.005253	0.591211	0.560413	0.029*
H12C	1.047963	0.764777	0.587797	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Hg1	0.0112 (3)	0.0221 (3)	0.0114 (2)	0.0009 (2)	0.00382 (17)	−0.0022 (2)
Hg2	0.0094 (2)	0.0196 (2)	0.0112 (2)	−0.0019 (2)	0.00269 (17)	−0.0017 (2)
Se1	0.0105 (6)	0.0109 (6)	0.0110 (6)	−0.0001 (5)	0.0023 (5)	0.0013 (5)
Cl1	0.0144 (16)	0.0140 (15)	0.0139 (15)	0.0005 (14)	0.0006 (12)	−0.0003 (12)
Cl2	0.029 (2)	0.027 (2)	0.0179 (16)	−0.0016 (18)	0.0096 (15)	−0.0063 (16)
Cl3	0.0094 (16)	0.028 (2)	0.0261 (19)	−0.0010 (15)	0.0020 (13)	−0.0119 (16)
N1	0.008 (5)	0.020 (6)	0.021 (5)	0.003 (4)	0.003 (4)	0.002 (5)
N2	0.013 (5)	0.014 (6)	0.016 (5)	0.002 (4)	0.006 (4)	0.004 (4)
C1	0.013 (5)	0.009 (5)	0.013 (5)	0.000 (4)	−0.001 (4)	0.001 (4)
C2	0.011 (5)	0.012 (5)	0.015 (4)	0.000 (4)	−0.005 (4)	0.002 (4)
C3	0.018 (6)	0.013 (6)	0.016 (5)	0.001 (5)	−0.003 (4)	0.002 (5)
C4	0.023 (6)	0.013 (5)	0.012 (5)	−0.001 (5)	−0.007 (4)	0.007 (5)
C5	0.020 (6)	0.015 (6)	0.013 (5)	−0.006 (5)	−0.004 (4)	0.003 (4)
C6	0.016 (5)	0.011 (5)	0.007 (4)	0.003 (4)	0.001 (4)	−0.002 (4)
C7	0.009 (5)	0.014 (5)	0.018 (5)	0.001 (5)	−0.004 (4)	0.002 (4)
C8	0.010 (7)	0.027 (8)	0.033 (8)	0.003 (6)	0.007 (6)	0.003 (7)
C9	0.027 (9)	0.015 (6)	0.027 (8)	0.005 (6)	−0.004 (7)	0.000 (6)
C10	0.018 (5)	0.014 (5)	0.011 (5)	0.000 (5)	0.002 (4)	−0.003 (5)
C11	0.026 (8)	0.016 (6)	0.016 (6)	−0.001 (6)	0.010 (6)	0.007 (6)
C12	0.010 (6)	0.023 (8)	0.026 (7)	0.000 (6)	0.007 (5)	−0.003 (7)

Geometric parameters (Å, º)

Hg1—Cl2	2.364 (4)	C3—C4	1.39 (3)
Hg1—N1	2.427 (13)	C3—H3A	0.9500
Hg1—Se1	2.5449 (16)	C4—C5	1.38 (3)
Hg1—Cl1	2.809 (4)	C4—H4A	0.9500
Hg1—Hg2	3.2995 (9)	C5—C6	1.420 (19)
Hg1—Cl1^i	3.376 (4)	C5—H5A	0.9500
Hg2—Cl3	2.358 (4)	C6—C10	1.50 (2)
Hg2—N2	2.442 (14)	C7—H7A	0.9900
Hg2—Se1	2.5334 (16)	C7—H7B	0.9900
Hg2—Cl1	2.766 (4)	C8—H8A	0.9800
Hg2—Cl1^i	3.297 (4)	C8—H8B	0.9800
Se1—C1	1.936 (14)	C8—H8C	0.9800
Se1—N1	3.619 (15)	C9—H9A	0.9800
Se1—N2	3.630 (15)	C9—H9B	0.9800
N1—C9	1.46 (2)	C9—H9C	0.9800
N1—C7	1.48 (2)	C10—H10A	0.9900
N1—C8	1.50 (2)	C10—H10B	0.9900
N2—C11	1.46 (2)	C11—H11A	0.9800
N2—C12	1.46 (2)	C11—H11B	0.9800
N2—C10	1.49 (2)	C11—H11C	0.9800
C1—C6	1.42 (2)	C12—H12A	0.9800
C1—C2	1.42 (2)	C12—H12B	0.9800
C2—C3	1.39 (2)	C12—H12C	0.9800
C2—C7	1.50 (2)
Cl2—Hg1—N1	100.9 (4)	C12—N2—Se1	125.2 (10)
Cl2—Hg1—Se1	160.22 (13)	C10—N2—Se1	63.5 (8)
N1—Hg1—Se1	93.4 (4)	Hg2—N2—Se1	44.2 (2)
Cl2—Hg1—Cl1	102.99 (14)	C6—C1—C2	120.9 (13)
N1—Hg1—Cl1	97.4 (4)	C6—C1—Se1	119.6 (11)
Se1—Hg1—Cl1	88.45 (9)	C2—C1—Se1	119.3 (11)
Cl2—Hg1—Hg2	126.64 (12)	C3—C2—C1	118.3 (16)
N1—Hg1—Hg2	126.4 (4)	C3—C2—C7	118.8 (15)
Se1—Hg1—Hg2	49.33 (4)	C1—C2—C7	122.9 (13)
Cl1—Hg1—Hg2	53.11 (9)	C4—C3—C2	122.2 (17)
Cl2—Hg1—Cl1^i	93.71 (14)	C4—C3—H3A	118.9
N1—Hg1—Cl1^i	149.0 (4)	C2—C3—H3A	118.9
Se1—Hg1—Cl1^i	67.42 (7)	C5—C4—C3	119.3 (14)
Cl1—Hg1—Cl1^i	105.76 (5)	C5—C4—H4A	120.4
Hg2—Hg1—Cl1^i	59.17 (7)	C3—C4—H4A	120.4
Cl3—Hg2—N2	102.2 (4)	C4—C5—C6	121.6 (18)
Cl3—Hg2—Se1	157.47 (13)	C4—C5—H5A	119.2
N2—Hg2—Se1	93.7 (3)	C6—C5—H5A	119.2
Cl3—Hg2—Cl1	104.37 (14)	C1—C6—C5	117.7 (16)
N2—Hg2—Cl1	95.6 (3)	C1—C6—C10	124.4 (12)
Se1—Hg2—Cl1	89.65 (9)	C5—C6—C10	117.8 (16)
Cl3—Hg2—Cl1^i	89.64 (14)	N1—C7—C2	116.4 (14)
N2—Hg2—Cl1^i	149.2 (3)	N1—C7—H7A	108.2
Se1—Hg2—Cl1^i	68.92 (7)	C2—C7—H7A	108.2
Cl1—Hg2—Cl1^i	108.96 (5)	N1—C7—H7B	108.2
Cl3—Hg2—Hg1	126.29 (11)	C2—C7—H7B	108.2
N2—Hg2—Hg1	126.1 (3)	H7A—C7—H7B	107.3
Se1—Hg2—Hg1	49.63 (4)	N1—C8—H8A	109.5
Cl1—Hg2—Hg1	54.33 (9)	N1—C8—H8B	109.5
Cl1^i—Hg2—Hg1	61.57 (7)	H8A—C8—H8B	109.5
C1—Se1—Hg2	98.2 (5)	N1—C8—H8C	109.5
C1—Se1—Hg1	98.2 (5)	H8A—C8—H8C	109.5
Hg2—Se1—Hg1	81.04 (5)	H8B—C8—H8C	109.5
C1—Se1—N1	66.4 (5)	N1—C9—H9A	109.5
Hg2—Se1—N1	111.6 (2)	N1—C9—H9B	109.5
Hg1—Se1—N1	42.0 (2)	H9A—C9—H9B	109.5
C1—Se1—N2	65.7 (5)	N1—C9—H9C	109.5
Hg2—Se1—N2	42.2 (2)	H9A—C9—H9C	109.5
Hg1—Se1—N2	111.2 (2)	H9B—C9—H9C	109.5
N1—Se1—N2	116.9 (3)	N2—C10—C6	114.2 (13)
Hg2—Cl1—Hg1	72.57 (9)	N2—C10—H10A	108.7
C9—N1—C7	111.9 (13)	C6—C10—H10A	108.7
C9—N1—C8	110.8 (15)	N2—C10—H10B	108.7
C7—N1—C8	108.8 (14)	C6—C10—H10B	108.7
C9—N1—Hg1	111.9 (11)	H10A—C10—H10B	107.6
C7—N1—Hg1	106.4 (9)	N2—C11—H11A	109.5
C8—N1—Hg1	106.8 (10)	N2—C11—H11B	109.5
C9—N1—Se1	123.7 (12)	H11A—C11—H11B	109.5
C7—N1—Se1	62.1 (8)	N2—C11—H11C	109.5
C8—N1—Se1	124.4 (10)	H11A—C11—H11C	109.5
Hg1—N1—Se1	44.6 (2)	H11B—C11—H11C	109.5
C11—N2—C12	110.6 (14)	N2—C12—H12A	109.5
C11—N2—C10	111.0 (12)	N2—C12—H12B	109.5
C12—N2—C10	110.0 (13)	H12A—C12—H12B	109.5
C11—N2—Hg2	112.3 (10)	N2—C12—H12C	109.5
C12—N2—Hg2	105.6 (9)	H12A—C12—H12C	109.5
C10—N2—Hg2	107.3 (9)	H12B—C12—H12C	109.5
C11—N2—Se1	122.7 (11)
C6—C1—C2—C3	−1 (2)	C4—C5—C6—C10	175.1 (15)
Se1—C1—C2—C3	−176.4 (12)	C9—N1—C7—C2	53.9 (18)
C6—C1—C2—C7	175.6 (14)	C8—N1—C7—C2	176.6 (13)
Se1—C1—C2—C7	0 (2)	Hg1—N1—C7—C2	−68.6 (13)
C1—C2—C3—C4	1 (2)	Se1—N1—C7—C2	−63.7 (11)
C7—C2—C3—C4	−176.2 (15)	C3—C2—C7—N1	−102.2 (16)
C2—C3—C4—C5	0 (3)	C1—C2—C7—N1	81.2 (19)
C3—C4—C5—C6	1 (2)	C11—N2—C10—C6	−55.2 (18)
C2—C1—C6—C5	1 (2)	C12—N2—C10—C6	−177.9 (13)
Se1—C1—C6—C5	176.7 (11)	Hg2—N2—C10—C6	67.7 (13)
C2—C1—C6—C10	−174.7 (14)	Se1—N2—C10—C6	61.8 (11)
Se1—C1—C6—C10	0.6 (19)	C1—C6—C10—N2	−80.2 (18)
C4—C5—C6—C1	−1 (2)	C5—C6—C10—N2	103.7 (15)

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cl3^ii	0.98	2.81	3.479 (18)	127
C8—H8C···Cl3^i	0.98	2.77	3.67 (2)	154
C12—H12A···Cl2^iii	0.98	2.88	3.814 (18)	159
C12—H12B···Cl2^i	0.98	2.96	3.84 (2)	150
C12—H12C···Cl3	0.98	2.97	3.657 (18)	128

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) x+1/2, −y+3/2, z−1/2.