Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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 PdII and HgII 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:C1′,N2′}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 HgII 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°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620010311/fn3335sup1.cif
Contains datablocks 14, 15, 16, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620010311/fn333514sup2.hkl
Contains datablock 14

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620010311/fn333515sup3.hkl
Contains datablock 15

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229620010311/fn333516sup4.hkl
Contains datablock 16

CCDC references: 2018902; 2018901; 2018900

Computing details top

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) top
Crystal data top
C24H38N4SeF(000) = 976
Mr = 461.54Dx = 1.241 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.9417 (3) ÅCell parameters from 12119 reflections
b = 29.0031 (6) Åθ = 2.3–27.3°
c = 10.2398 (3) ŵ = 1.54 mm1
β = 111.572 (4)°T = 120 K
V = 2469.55 (14) Å3Prism, orange
Z = 40.33 × 0.26 × 0.18 mm
Data collection top
Rigaku Saturn 724 Dual Source CCD
diffractometer
4617 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.023
ω scansθmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2019)
h = 1010
Tmin = 0.653, Tmax = 0.786k = 1636
16025 measured reflectionsl = 1212
5013 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0259P)2 + 1.2484P]
where P = (Fo2 + 2Fc2)/3
5013 reflections(Δ/σ)max = 0.002
270 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.26 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Se10.61845 (2)0.33765 (2)0.40458 (2)0.01303 (5)
N1A0.56051 (15)0.29275 (4)0.10664 (13)0.0182 (3)
N2A0.15431 (14)0.39116 (4)0.44403 (13)0.0164 (2)
N1B0.79086 (15)0.29743 (4)0.70261 (13)0.0181 (3)
N2B0.71373 (15)0.48656 (4)0.30274 (13)0.0192 (3)
C1B0.69907 (16)0.38827 (5)0.53679 (14)0.0139 (3)
C1A0.44067 (17)0.36871 (4)0.26112 (14)0.0142 (3)
C2A0.43523 (18)0.36711 (5)0.12159 (15)0.0167 (3)
C2B0.71804 (16)0.37979 (5)0.67768 (15)0.0155 (3)
C3A0.30749 (18)0.38784 (5)0.01577 (15)0.0197 (3)
H3AA0.3027420.3867150.0783960.024*
C3B0.77076 (17)0.41537 (5)0.77507 (15)0.0188 (3)
H3BA0.7823870.4100850.8698770.023*
C4A0.18653 (19)0.41021 (5)0.04597 (16)0.0214 (3)
H4AA0.1005230.4246870.0269110.026*
C4B0.80663 (18)0.45856 (5)0.73544 (16)0.0213 (3)
H4BA0.8385980.4829200.8020170.026*
C5B0.79562 (18)0.46595 (5)0.59858 (16)0.0192 (3)
H5BA0.8236000.4952520.5728610.023*
C5A0.19211 (18)0.41128 (5)0.18301 (16)0.0189 (3)
H5AA0.1089840.4265240.2030870.023*
C6B0.74393 (16)0.43098 (5)0.49733 (15)0.0155 (3)
C6A0.31754 (17)0.39038 (5)0.29232 (15)0.0152 (3)
C7A0.56599 (19)0.34280 (5)0.08725 (15)0.0178 (3)
H7AA0.5525730.3494150.0112750.021*
H7AB0.6722830.3547430.1487940.021*
C7B0.68455 (18)0.33272 (5)0.72380 (15)0.0172 (3)
H7BA0.6995180.3338250.8244730.021*
H7BB0.5712790.3242370.6698570.021*
C8A0.7158 (2)0.27148 (5)0.12962 (16)0.0236 (3)
H8AA0.7093100.2382880.1446200.035*
H8AB0.7979020.2852540.2124840.035*
H8AC0.7446100.2766050.0472110.035*
C8B0.7311 (2)0.25133 (5)0.71549 (17)0.0253 (3)
H8BA0.8040240.2280790.7026190.038*
H8BB0.6235250.2472200.6436150.038*
H8BC0.7257160.2478110.8088470.038*
C9B0.95556 (19)0.30328 (6)0.80101 (17)0.0262 (3)
H9BA1.0230750.2786850.7866540.039*
H9BB0.9578960.3018260.8973630.039*
H9BC0.9965040.3332770.7852340.039*
C9A0.4339 (2)0.27182 (5)0.01324 (16)0.0250 (3)
H9AA0.4237610.2391110.0060490.037*
H9AB0.4613440.2747950.0971160.037*
H9AC0.3316580.2875210.0290480.037*
C10A0.31633 (17)0.39211 (5)0.43994 (15)0.0171 (3)
H10A0.3780490.3655190.4938850.021*
H10B0.3714120.4205890.4865770.021*
C10B0.75399 (18)0.43933 (5)0.35454 (15)0.0171 (3)
H10C0.8645270.4322580.3602190.021*
H10D0.6799700.4177850.2859380.021*
C11A0.16618 (19)0.39812 (5)0.58899 (16)0.0221 (3)
H11A0.2126230.4285410.6215700.033*
H11B0.2351380.3742100.6490460.033*
H11C0.0587380.3962690.5934690.033*
C11B0.54322 (19)0.49610 (6)0.26906 (18)0.0268 (3)
H11D0.5198310.5280370.2367020.040*
H11E0.5169800.4915700.3530530.040*
H11F0.4784420.4751030.1948360.040*
C12A0.0765 (2)0.34683 (5)0.39286 (17)0.0234 (3)
H12A0.0640200.3427680.2943750.035*
H12B0.0294730.3462120.4006150.035*
H12C0.1429800.3218310.4493290.035*
C12B0.7540 (2)0.49281 (6)0.17780 (18)0.0283 (4)
H12D0.7261430.5242350.1419060.042*
H12E0.6932450.4706380.1055260.042*
H12F0.8694240.4877440.2022060.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Se10.01277 (8)0.01188 (7)0.01350 (8)0.00028 (5)0.00373 (6)0.00024 (5)
N1A0.0207 (7)0.0164 (6)0.0157 (6)0.0007 (5)0.0045 (5)0.0028 (5)
N2A0.0134 (6)0.0167 (6)0.0199 (6)0.0000 (5)0.0070 (5)0.0011 (5)
N1B0.0201 (7)0.0160 (6)0.0175 (6)0.0028 (5)0.0061 (5)0.0025 (5)
N2B0.0184 (6)0.0157 (6)0.0230 (7)0.0001 (5)0.0072 (5)0.0048 (5)
C1B0.0099 (6)0.0150 (6)0.0145 (7)0.0013 (5)0.0019 (5)0.0010 (5)
C1A0.0136 (7)0.0115 (6)0.0153 (7)0.0023 (5)0.0026 (6)0.0009 (5)
C2A0.0183 (7)0.0139 (6)0.0171 (7)0.0036 (5)0.0058 (6)0.0001 (5)
C2B0.0110 (7)0.0181 (7)0.0167 (7)0.0030 (5)0.0043 (6)0.0008 (5)
C3A0.0234 (8)0.0200 (7)0.0131 (7)0.0039 (6)0.0036 (6)0.0017 (5)
C3B0.0167 (7)0.0227 (7)0.0151 (7)0.0039 (6)0.0037 (6)0.0015 (6)
C4A0.0177 (8)0.0213 (7)0.0197 (7)0.0008 (6)0.0006 (6)0.0059 (6)
C4B0.0194 (8)0.0199 (7)0.0209 (8)0.0007 (6)0.0030 (6)0.0057 (6)
C5B0.0158 (7)0.0155 (7)0.0238 (8)0.0002 (6)0.0044 (6)0.0004 (6)
C5A0.0146 (7)0.0178 (7)0.0226 (8)0.0003 (6)0.0050 (6)0.0024 (6)
C6B0.0100 (7)0.0156 (6)0.0186 (7)0.0021 (5)0.0024 (6)0.0005 (5)
C6A0.0127 (7)0.0139 (6)0.0174 (7)0.0030 (5)0.0035 (6)0.0005 (5)
C7A0.0221 (8)0.0182 (7)0.0142 (7)0.0026 (6)0.0079 (6)0.0006 (5)
C7B0.0180 (7)0.0200 (7)0.0147 (7)0.0015 (6)0.0073 (6)0.0021 (5)
C8A0.0269 (9)0.0227 (8)0.0202 (8)0.0024 (6)0.0076 (7)0.0029 (6)
C8B0.0342 (10)0.0184 (7)0.0258 (8)0.0010 (7)0.0138 (7)0.0028 (6)
C9B0.0220 (8)0.0270 (8)0.0253 (8)0.0065 (6)0.0036 (7)0.0034 (7)
C9A0.0263 (9)0.0247 (8)0.0210 (8)0.0043 (7)0.0053 (7)0.0071 (6)
C10A0.0129 (7)0.0203 (7)0.0175 (7)0.0002 (5)0.0048 (6)0.0000 (6)
C10B0.0171 (7)0.0143 (6)0.0195 (7)0.0003 (5)0.0062 (6)0.0016 (5)
C11A0.0203 (8)0.0257 (8)0.0229 (8)0.0025 (6)0.0110 (7)0.0006 (6)
C11B0.0216 (8)0.0243 (8)0.0318 (9)0.0056 (6)0.0065 (7)0.0066 (7)
C12A0.0238 (8)0.0198 (7)0.0283 (9)0.0057 (6)0.0118 (7)0.0021 (6)
C12B0.0343 (10)0.0238 (8)0.0294 (9)0.0014 (7)0.0148 (8)0.0077 (7)
Geometric parameters (Å, º) top
Se1—C1A1.9440 (14)C5A—H5AA0.9500
Se1—C1B1.9468 (13)C6B—C10B1.5170 (19)
Se1—N1B3.0969 (12)C6A—C10A1.5164 (19)
Se1—N1A3.1796 (12)C7A—H7AA0.9900
N1A—C8A1.457 (2)C7A—H7AB0.9900
N1A—C9A1.4612 (19)C7B—H7BA0.9900
N1A—C7A1.4683 (17)C7B—H7BB0.9900
N2A—C11A1.4626 (18)C8A—H8AA0.9800
N2A—C12A1.4640 (18)C8A—H8AB0.9800
N2A—C10A1.4650 (17)C8A—H8AC0.9800
N1B—C9B1.457 (2)C8B—H8BA0.9800
N1B—C8B1.4640 (19)C8B—H8BB0.9800
N1B—C7B1.4662 (18)C8B—H8BC0.9800
N2B—C11B1.461 (2)C9B—H9BA0.9800
N2B—C12B1.4619 (19)C9B—H9BB0.9800
N2B—C10B1.4653 (17)C9B—H9BC0.9800
C1B—C6B1.4065 (19)C9A—H9AA0.9800
C1B—C2B1.4108 (19)C9A—H9AB0.9800
C1A—C6A1.4029 (19)C9A—H9AC0.9800
C1A—C2A1.4124 (19)C10A—H10A0.9900
C2A—C3A1.389 (2)C10A—H10B0.9900
C2A—C7A1.513 (2)C10B—H10C0.9900
C2B—C3B1.391 (2)C10B—H10D0.9900
C2B—C7B1.5102 (19)C11A—H11A0.9800
C3A—C4A1.390 (2)C11A—H11B0.9800
C3A—H3AA0.9500C11A—H11C0.9800
C3B—C4B1.390 (2)C11B—H11D0.9800
C3B—H3BA0.9500C11B—H11E0.9800
C4A—C5A1.386 (2)C11B—H11F0.9800
C4A—H4AA0.9500C12A—H12A0.9800
C4B—C5B1.385 (2)C12A—H12B0.9800
C4B—H4BA0.9500C12A—H12C0.9800
C5B—C6B1.402 (2)C12B—H12D0.9800
C5B—H5BA0.9500C12B—H12E0.9800
C5A—C6A1.398 (2)C12B—H12F0.9800
C1A—Se1—C1B99.61 (6)N1B—C7B—C2B111.77 (11)
C1A—Se1—N1B153.08 (5)N1B—C7B—H7BA109.3
C1B—Se1—N1B71.09 (5)C2B—C7B—H7BA109.3
C1A—Se1—N1A70.44 (5)N1B—C7B—H7BB109.3
C1B—Se1—N1A149.78 (5)C2B—C7B—H7BB109.3
N1B—Se1—N1A129.62 (3)H7BA—C7B—H7BB107.9
C8A—N1A—C9A110.97 (12)N1A—C8A—H8AA109.5
C8A—N1A—C7A111.29 (12)N1A—C8A—H8AB109.5
C9A—N1A—C7A110.56 (12)H8AA—C8A—H8AB109.5
C8A—N1A—Se1102.06 (8)N1A—C8A—H8AC109.5
C9A—N1A—Se1141.15 (9)H8AA—C8A—H8AC109.5
C7A—N1A—Se173.92 (7)H8AB—C8A—H8AC109.5
C11A—N2A—C12A109.40 (11)N1B—C8B—H8BA109.5
C11A—N2A—C10A108.84 (11)N1B—C8B—H8BB109.5
C12A—N2A—C10A110.54 (11)H8BA—C8B—H8BB109.5
C9B—N1B—C8B110.72 (12)N1B—C8B—H8BC109.5
C9B—N1B—C7B111.22 (12)H8BA—C8B—H8BC109.5
C8B—N1B—C7B110.26 (12)H8BB—C8B—H8BC109.5
C9B—N1B—Se1130.41 (9)N1B—C9B—H9BA109.5
C8B—N1B—Se1111.52 (9)N1B—C9B—H9BB109.5
C7B—N1B—Se176.59 (7)H9BA—C9B—H9BB109.5
C11B—N2B—C12B109.95 (13)N1B—C9B—H9BC109.5
C11B—N2B—C10B111.02 (11)H9BA—C9B—H9BC109.5
C12B—N2B—C10B109.02 (11)H9BB—C9B—H9BC109.5
C6B—C1B—C2B120.50 (12)N1A—C9A—H9AA109.5
C6B—C1B—Se1122.43 (10)N1A—C9A—H9AB109.5
C2B—C1B—Se1117.02 (10)H9AA—C9A—H9AB109.5
C6A—C1A—C2A120.47 (13)N1A—C9A—H9AC109.5
C6A—C1A—Se1121.85 (10)H9AA—C9A—H9AC109.5
C2A—C1A—Se1117.63 (10)H9AB—C9A—H9AC109.5
C3A—C2A—C1A119.17 (13)N2A—C10A—C6A113.42 (12)
C3A—C2A—C7A120.29 (13)N2A—C10A—H10A108.9
C1A—C2A—C7A120.54 (13)C6A—C10A—H10A108.9
C3B—C2B—C1B119.04 (13)N2A—C10A—H10B108.9
C3B—C2B—C7B120.01 (13)C6A—C10A—H10B108.9
C1B—C2B—C7B120.94 (12)H10A—C10A—H10B107.7
C2A—C3A—C4A120.82 (13)N2B—C10B—C6B113.86 (11)
C2A—C3A—H3AA119.6N2B—C10B—H10C108.8
C4A—C3A—H3AA119.6C6B—C10B—H10C108.8
C4B—C3B—C2B120.85 (13)N2B—C10B—H10D108.8
C4B—C3B—H3BA119.6C6B—C10B—H10D108.8
C2B—C3B—H3BA119.6H10C—C10B—H10D107.7
C5A—C4A—C3A119.62 (14)N2A—C11A—H11A109.5
C5A—C4A—H4AA120.2N2A—C11A—H11B109.5
C3A—C4A—H4AA120.2H11A—C11A—H11B109.5
C5B—C4B—C3B119.79 (13)N2A—C11A—H11C109.5
C5B—C4B—H4BA120.1H11A—C11A—H11C109.5
C3B—C4B—H4BA120.1H11B—C11A—H11C109.5
C4B—C5B—C6B121.18 (13)N2B—C11B—H11D109.5
C4B—C5B—H5BA119.4N2B—C11B—H11E109.5
C6B—C5B—H5BA119.4H11D—C11B—H11E109.5
C4A—C5A—C6A121.36 (14)N2B—C11B—H11F109.5
C4A—C5A—H5AA119.3H11D—C11B—H11F109.5
C6A—C5A—H5AA119.3H11E—C11B—H11F109.5
C5B—C6B—C1B118.43 (13)N2A—C12A—H12A109.5
C5B—C6B—C10B118.49 (12)N2A—C12A—H12B109.5
C1B—C6B—C10B122.81 (12)H12A—C12A—H12B109.5
C5A—C6A—C1A118.53 (13)N2A—C12A—H12C109.5
C5A—C6A—C10A119.08 (12)H12A—C12A—H12C109.5
C1A—C6A—C10A122.39 (12)H12B—C12A—H12C109.5
N1A—C7A—C2A111.24 (11)N2B—C12B—H12D109.5
N1A—C7A—H7AA109.4N2B—C12B—H12E109.5
C2A—C7A—H7AA109.4H12D—C12B—H12E109.5
N1A—C7A—H7AB109.4N2B—C12B—H12F109.5
C2A—C7A—H7AB109.4H12D—C12B—H12F109.5
H7AA—C7A—H7AB108.0H12E—C12B—H12F109.5
C6A—C1A—C2A—C3A0.9 (2)C4A—C5A—C6A—C10A179.22 (13)
Se1—C1A—C2A—C3A178.23 (10)C2A—C1A—C6A—C5A1.6 (2)
C6A—C1A—C2A—C7A178.59 (12)Se1—C1A—C6A—C5A178.83 (10)
Se1—C1A—C2A—C7A1.25 (17)C2A—C1A—C6A—C10A178.70 (12)
C6B—C1B—C2B—C3B4.6 (2)Se1—C1A—C6A—C10A1.47 (18)
Se1—C1B—C2B—C3B178.10 (10)C8A—N1A—C7A—C2A157.07 (12)
C6B—C1B—C2B—C7B174.40 (13)C9A—N1A—C7A—C2A79.13 (15)
Se1—C1B—C2B—C7B2.88 (17)Se1—N1A—C7A—C2A60.12 (10)
C1A—C2A—C3A—C4A0.4 (2)C3A—C2A—C7A—N1A111.26 (15)
C7A—C2A—C3A—C4A179.89 (13)C1A—C2A—C7A—N1A68.21 (17)
C1B—C2B—C3B—C4B0.9 (2)C9B—N1B—C7B—C2B70.47 (15)
C7B—C2B—C3B—C4B178.13 (13)C8B—N1B—C7B—C2B166.31 (12)
C2A—C3A—C4A—C5A1.0 (2)Se1—N1B—C7B—C2B58.01 (10)
C2B—C3B—C4B—C5B2.4 (2)C3B—C2B—C7B—N1B117.48 (14)
C3B—C4B—C5B—C6B2.0 (2)C1B—C2B—C7B—N1B61.53 (17)
C3A—C4A—C5A—C6A0.2 (2)C11A—N2A—C10A—C6A173.77 (11)
C4B—C5B—C6B—C1B1.7 (2)C12A—N2A—C10A—C6A66.06 (15)
C4B—C5B—C6B—C10B172.60 (13)C5A—C6A—C10A—N2A32.96 (17)
C2B—C1B—C6B—C5B5.0 (2)C1A—C6A—C10A—N2A147.35 (13)
Se1—C1B—C6B—C5B177.90 (10)C11B—N2B—C10B—C6B68.42 (16)
C2B—C1B—C6B—C10B169.02 (13)C12B—N2B—C10B—C6B170.30 (13)
Se1—C1B—C6B—C10B8.11 (19)C5B—C6B—C10B—N2B38.24 (18)
C4A—C5A—C6A—C1A1.1 (2)C1B—C6B—C10B—N2B147.78 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10A—H10A···Se10.992.753.2623 (14)113
C10B—H10D···Se10.992.773.2992 (14)114
C11A—H11A···N2Bi0.982.593.563 (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:C1',N2'}bis[dichloridopalladium(II)] (15) top
Crystal data top
[Pd2Cl4(C24H38N4Se)]F(000) = 3232
Mr = 816.14Dx = 1.365 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.422 (1) ÅCell parameters from 9802 reflections
b = 21.8012 (10) Åθ = 2.8–28.4°
c = 19.1405 (10) ŵ = 2.11 mm1
β = 117.290 (2)°T = 100 K
V = 7944.1 (7) Å3Plate, brown
Z = 80.26 × 0.25 × 0.08 mm
Data collection top
Bruker Quest
diffractometer
7722 reflections with I > 2σ(I)
ω scansRint = 0.032
Absorption correction: analytical
(APEX2; Bruker, 2005)
θmax = 28.4°, θmin = 2.3°
Tmin = 0.583, Tmax = 0.945h = 2428
27098 measured reflectionsk = 2829
9460 independent reflectionsl = 2517
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: mixed
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0185P)2 + 71.8262P]
where P = (Fo2 + 2Fc2)/3
9460 reflections(Δ/σ)max = 0.001
331 parametersΔρmax = 1.16 e Å3
2 restraintsΔρmin = 1.42 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pd10.59869 (2)0.05743 (2)0.47261 (2)0.02383 (8)
Se1A0.5000000.13801 (2)0.2500000.02063 (11)
Cl1A0.70577 (5)0.10481 (5)0.57390 (7)0.0323 (2)
Cl2A0.53094 (6)0.13521 (5)0.48594 (7)0.0312 (2)
N1A0.65190 (17)0.01586 (17)0.4525 (2)0.0272 (7)
N2A0.3529 (2)0.17182 (16)0.3198 (2)0.0281 (7)
H2AA0.355 (3)0.155 (2)0.360 (2)0.034*
C1A0.5154 (2)0.01040 (18)0.3988 (2)0.0239 (8)
C2A0.53077 (19)0.03635 (18)0.3577 (2)0.0209 (7)
C3A0.47963 (19)0.07845 (17)0.3118 (2)0.0196 (7)
C4A0.4125 (2)0.07638 (17)0.3079 (2)0.0222 (7)
C5A0.3978 (2)0.02871 (19)0.3474 (3)0.0259 (8)
H5AA0.3520970.0256750.3437210.031*
C6A0.4488 (2)0.01430 (18)0.3920 (2)0.0246 (8)
H6AA0.4374700.0464100.4177980.030*
C7A0.6051 (2)0.03783 (19)0.3702 (2)0.0250 (8)
H7AA0.6181350.0801050.3631580.030*
H7AB0.6102870.0108650.3315330.030*
C8A0.7218 (2)0.0007 (2)0.4597 (3)0.0363 (10)
H8AA0.7413510.0368650.4461970.054*
H8AB0.7173540.0329200.4237370.054*
H8AC0.7531330.0117300.5138030.054*
C9A0.6592 (2)0.0657 (2)0.5083 (3)0.0307 (9)
H9AA0.6854270.0998710.5009950.046*
H9AB0.6845970.0503400.5622710.046*
H9AC0.6125410.0799530.4985300.046*
C10A0.3549 (2)0.12247 (18)0.2652 (3)0.0255 (8)
H10A0.3090850.1009950.2406620.031*
H10B0.3622630.1417880.2227940.031*
C11A0.4123 (3)0.2147 (2)0.3443 (3)0.0344 (10)
H11A0.4086960.2460810.3788890.052*
H11B0.4113500.2343730.2977530.052*
H11C0.4565500.1921810.3725230.052*
C12A0.2843 (3)0.2052 (2)0.2814 (3)0.0360 (10)
H12A0.2850990.2396860.3146410.054*
H12B0.2461350.1771710.2741910.054*
H12C0.2768680.2207720.2300460.054*
Pd20.41782 (2)0.42261 (2)0.36778 (2)0.02558 (8)
Se1B0.5000000.63190 (3)0.2500000.02969 (14)
Cl1B0.31592 (6)0.36455 (5)0.35503 (8)0.0411 (3)
Cl2B0.49272 (6)0.35269 (5)0.45935 (7)0.0351 (2)
N1B0.35807 (19)0.48686 (18)0.2830 (2)0.0315 (8)
N2B0.6116 (2)0.68782 (16)0.4641 (2)0.0304 (8)
H2BA0.604 (3)0.673 (2)0.502 (2)0.036*
C1B0.4936 (2)0.48115 (18)0.3851 (2)0.0225 (8)
C2B0.4763 (2)0.52518 (18)0.3253 (2)0.0235 (8)
C3B0.5216 (2)0.57438 (17)0.3352 (2)0.0231 (8)
C4B0.5827 (2)0.58241 (18)0.4057 (3)0.0239 (8)
C5B0.5988 (2)0.53807 (18)0.4644 (3)0.0241 (8)
H5BA0.6403740.5424580.5126530.029*
C6B0.5556 (2)0.48803 (18)0.4539 (2)0.0247 (8)
H6BA0.5686800.4581080.4942520.030*
C7B0.4060 (2)0.51609 (18)0.2548 (2)0.0244 (8)
H7BA0.3866570.5560240.2295340.029*
H7BB0.4109100.4892690.2158320.029*
C8B0.2969 (3)0.4609 (3)0.2132 (3)0.0446 (13)
H8BA0.2742620.4933970.1742720.067*
H8BB0.2631300.4440420.2294510.067*
H8BC0.3129540.4283250.1901000.067*
C9B0.3337 (3)0.5340 (2)0.3192 (3)0.0404 (11)
H9BA0.3045420.5638220.2792020.061*
H9BB0.3743040.5549990.3605530.061*
H9BC0.3059880.5148080.3421680.061*
C10B0.6315 (2)0.63673 (19)0.4247 (3)0.0290 (9)
H10C0.6303720.6524210.3755470.035*
H10D0.6801640.6233110.4597770.035*
C11B0.5438 (3)0.71755 (19)0.4100 (3)0.0335 (10)
H11D0.5321170.7490380.4385960.050*
H11E0.5065120.6865770.3896730.050*
H11F0.5482220.7365600.3660390.050*
C12B0.6685 (3)0.7345 (2)0.4960 (3)0.0468 (13)
H12D0.6534090.7691710.5171650.070*
H12E0.6788650.7489500.4539450.070*
H12F0.7108570.7161180.5380350.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pd10.02879 (15)0.02520 (15)0.02320 (15)0.00442 (12)0.01682 (12)0.00370 (11)
Se1A0.0233 (2)0.0222 (2)0.0186 (3)0.0000.0115 (2)0.000
Cl1A0.0318 (5)0.0365 (5)0.0353 (6)0.0103 (4)0.0210 (4)0.0116 (4)
Cl2A0.0396 (5)0.0223 (5)0.0349 (6)0.0017 (4)0.0199 (5)0.0002 (4)
N1A0.0226 (16)0.0366 (19)0.0262 (18)0.0046 (14)0.0146 (14)0.0097 (15)
N2A0.0377 (19)0.0268 (17)0.0278 (19)0.0039 (15)0.0219 (16)0.0020 (14)
C1A0.032 (2)0.0251 (19)0.0182 (18)0.0018 (16)0.0145 (16)0.0020 (14)
C2A0.0166 (16)0.0287 (19)0.0183 (18)0.0011 (14)0.0090 (14)0.0018 (14)
C3A0.0224 (17)0.0243 (18)0.0160 (17)0.0008 (14)0.0121 (14)0.0021 (14)
C4A0.0249 (18)0.0223 (18)0.0214 (19)0.0010 (14)0.0122 (15)0.0027 (14)
C5A0.0275 (19)0.029 (2)0.030 (2)0.0029 (16)0.0205 (17)0.0051 (16)
C6A0.030 (2)0.0226 (18)0.027 (2)0.0015 (15)0.0188 (17)0.0018 (15)
C7A0.0237 (18)0.030 (2)0.025 (2)0.0044 (15)0.0139 (16)0.0086 (16)
C8A0.028 (2)0.045 (3)0.043 (3)0.0093 (19)0.022 (2)0.015 (2)
C9A0.026 (2)0.037 (2)0.025 (2)0.0061 (17)0.0081 (17)0.0024 (17)
C10A0.0255 (19)0.0265 (19)0.028 (2)0.0017 (15)0.0155 (17)0.0044 (16)
C11A0.046 (3)0.026 (2)0.032 (2)0.0029 (19)0.018 (2)0.0044 (17)
C12A0.043 (3)0.029 (2)0.043 (3)0.0129 (19)0.026 (2)0.0057 (19)
Pd20.03141 (16)0.02333 (15)0.02325 (16)0.00183 (12)0.01361 (13)0.00145 (11)
Se1B0.0537 (4)0.0189 (3)0.0227 (3)0.0000.0229 (3)0.000
Cl1B0.0407 (6)0.0351 (6)0.0427 (7)0.0112 (5)0.0150 (5)0.0053 (5)
Cl2B0.0445 (6)0.0246 (5)0.0376 (6)0.0045 (4)0.0199 (5)0.0078 (4)
N1B0.0283 (18)0.038 (2)0.0274 (19)0.0010 (15)0.0118 (15)0.0065 (15)
N2B0.040 (2)0.0223 (17)0.032 (2)0.0089 (15)0.0190 (17)0.0008 (14)
C1B0.0271 (19)0.0238 (18)0.0207 (19)0.0001 (15)0.0145 (16)0.0027 (14)
C2B0.032 (2)0.0235 (18)0.0203 (18)0.0045 (15)0.0162 (16)0.0011 (14)
C3B0.034 (2)0.0192 (17)0.025 (2)0.0038 (15)0.0221 (17)0.0011 (14)
C4B0.0295 (19)0.0222 (18)0.031 (2)0.0006 (15)0.0232 (17)0.0009 (15)
C5B0.0264 (19)0.0222 (18)0.029 (2)0.0060 (15)0.0170 (17)0.0033 (15)
C6B0.0291 (19)0.0236 (19)0.024 (2)0.0039 (15)0.0146 (16)0.0005 (15)
C7B0.031 (2)0.0269 (19)0.0172 (18)0.0021 (16)0.0126 (16)0.0036 (15)
C8B0.035 (2)0.057 (3)0.034 (3)0.007 (2)0.009 (2)0.011 (2)
C9B0.041 (3)0.045 (3)0.044 (3)0.018 (2)0.028 (2)0.017 (2)
C10B0.032 (2)0.030 (2)0.034 (2)0.0037 (17)0.0233 (19)0.0003 (17)
C11B0.048 (3)0.023 (2)0.035 (2)0.0021 (18)0.023 (2)0.0060 (17)
C12B0.055 (3)0.039 (3)0.042 (3)0.024 (2)0.019 (3)0.004 (2)
Geometric parameters (Å, º) top
Pd1—C1A1.980 (4)Pd2—C1B1.969 (4)
Pd1—N1A2.098 (4)Pd2—N1B2.081 (4)
Pd1—Cl2A2.3209 (11)Pd2—Cl2B2.3220 (11)
Pd1—Cl1A2.4515 (11)Pd2—Cl1B2.4368 (12)
Se1A—C3A1.936 (4)Se1B—C3Bi1.937 (4)
Se1A—C3Ai1.936 (4)Se1B—C3B1.938 (4)
N1A—C8A1.477 (5)N1B—C9B1.464 (6)
N1A—C9A1.481 (6)N1B—C8B1.488 (6)
N1A—C7A1.506 (5)N1B—C7B1.504 (5)
N2A—C11A1.472 (6)N2B—C12B1.488 (6)
N2A—C12A1.497 (6)N2B—C11B1.491 (6)
N2A—C10A1.513 (5)N2B—C10B1.512 (6)
N2A—H2AA0.836 (19)N2B—H2BA0.860 (19)
C1A—C6A1.374 (6)C1B—C6B1.384 (5)
C1A—C2A1.415 (6)C1B—C2B1.408 (6)
C2A—C3A1.390 (5)C2B—C3B1.399 (6)
C2A—C7A1.498 (5)C2B—C7B1.505 (5)
C3A—C4A1.406 (5)C3B—C4B1.394 (6)
C4A—C5A1.404 (6)C4B—C5B1.400 (6)
C4A—C10A1.509 (5)C4B—C10B1.510 (6)
C5A—C6A1.395 (6)C5B—C6B1.384 (6)
C5A—H5AA0.9500C5B—H5BA0.9500
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—H7AA0.9900C7B—H7BA0.9900
C7A—H7AB0.9900C7B—H7BB0.9900
C8A—H8AA0.9800C8B—H8BA0.9800
C8A—H8AB0.9800C8B—H8BB0.9800
C8A—H8AC0.9800C8B—H8BC0.9800
C9A—H9AA0.9800C9B—H9BA0.9800
C9A—H9AB0.9800C9B—H9BB0.9800
C9A—H9AC0.9800C9B—H9BC0.9800
C10A—H10A0.9900C10B—H10C0.9900
C10A—H10B0.9900C10B—H10D0.9900
C11A—H11A0.9800C11B—H11D0.9800
C11A—H11B0.9800C11B—H11E0.9800
C11A—H11C0.9800C11B—H11F0.9800
C12A—H12A0.9800C12B—H12D0.9800
C12A—H12B0.9800C12B—H12E0.9800
C12A—H12C0.9800C12B—H12F0.9800
C1A—Pd1—N1A82.10 (15)C1B—Pd2—N1B81.94 (15)
C1A—Pd1—Cl2A93.00 (12)C1B—Pd2—Cl2B93.86 (12)
N1A—Pd1—Cl2A175.02 (10)N1B—Pd2—Cl2B174.73 (11)
C1A—Pd1—Cl1A173.22 (12)C1B—Pd2—Cl1B169.92 (12)
N1A—Pd1—Cl1A94.35 (9)N1B—Pd2—Cl1B93.97 (11)
Cl2A—Pd1—Cl1A90.62 (4)Cl2B—Pd2—Cl1B90.68 (4)
C3A—Se1A—C3Ai95.8 (2)C3Bi—Se1B—C3B99.3 (2)
C8A—N1A—C9A109.2 (4)C9B—N1B—C8B109.4 (4)
C8A—N1A—C7A109.2 (3)C9B—N1B—C7B108.9 (4)
C9A—N1A—C7A108.7 (3)C8B—N1B—C7B107.8 (4)
C8A—N1A—Pd1115.2 (3)C9B—N1B—Pd2109.2 (3)
C9A—N1A—Pd1108.3 (3)C8B—N1B—Pd2114.7 (3)
C7A—N1A—Pd1106.1 (2)C7B—N1B—Pd2106.7 (2)
C11A—N2A—C12A111.0 (3)C12B—N2B—C11B110.0 (4)
C11A—N2A—C10A112.2 (3)C12B—N2B—C10B110.1 (4)
C12A—N2A—C10A109.8 (3)C11B—N2B—C10B112.4 (4)
C11A—N2A—H2AA108 (4)C12B—N2B—H2BA109 (4)
C12A—N2A—H2AA107 (4)C11B—N2B—H2BA104 (4)
C10A—N2A—H2AA109 (4)C10B—N2B—H2BA110 (4)
C6A—C1A—C2A119.2 (4)C6B—C1B—C2B118.6 (4)
C6A—C1A—Pd1126.3 (3)C6B—C1B—Pd2126.0 (3)
C2A—C1A—Pd1113.9 (3)C2B—C1B—Pd2114.6 (3)
C3A—C2A—C1A120.6 (3)C3B—C2B—C1B120.3 (4)
C3A—C2A—C7A123.9 (3)C3B—C2B—C7B124.7 (4)
C1A—C2A—C7A115.4 (3)C1B—C2B—C7B114.9 (4)
C2A—C3A—C4A120.2 (3)C4B—C3B—C2B120.8 (4)
C2A—C3A—Se1A119.7 (3)C4B—C3B—Se1B119.3 (3)
C4A—C3A—Se1A120.1 (3)C2B—C3B—Se1B119.9 (3)
C5A—C4A—C3A118.2 (4)C3B—C4B—C5B117.8 (4)
C5A—C4A—C10A117.0 (4)C3B—C4B—C10B124.8 (4)
C3A—C4A—C10A124.8 (4)C5B—C4B—C10B117.4 (4)
C6A—C5A—C4A121.3 (4)C6B—C5B—C4B121.7 (4)
C6A—C5A—H5AA119.3C6B—C5B—H5BA119.1
C4A—C5A—H5AA119.3C4B—C5B—H5BA119.1
C1A—C6A—C5A120.3 (4)C5B—C6B—C1B120.6 (4)
C1A—C6A—H6AA119.9C5B—C6B—H6BA119.7
C5A—C6A—H6AA119.9C1B—C6B—H6BA119.7
C2A—C7A—N1A108.0 (3)N1B—C7B—C2B107.6 (3)
C2A—C7A—H7AA110.1N1B—C7B—H7BA110.2
N1A—C7A—H7AA110.1C2B—C7B—H7BA110.2
C2A—C7A—H7AB110.1N1B—C7B—H7BB110.2
N1A—C7A—H7AB110.1C2B—C7B—H7BB110.2
H7AA—C7A—H7AB108.4H7BA—C7B—H7BB108.5
N1A—C8A—H8AA109.5N1B—C8B—H8BA109.5
N1A—C8A—H8AB109.5N1B—C8B—H8BB109.5
H8AA—C8A—H8AB109.5H8BA—C8B—H8BB109.5
N1A—C8A—H8AC109.5N1B—C8B—H8BC109.5
H8AA—C8A—H8AC109.5H8BA—C8B—H8BC109.5
H8AB—C8A—H8AC109.5H8BB—C8B—H8BC109.5
N1A—C9A—H9AA109.5N1B—C9B—H9BA109.5
N1A—C9A—H9AB109.5N1B—C9B—H9BB109.5
H9AA—C9A—H9AB109.5H9BA—C9B—H9BB109.5
N1A—C9A—H9AC109.5N1B—C9B—H9BC109.5
H9AA—C9A—H9AC109.5H9BA—C9B—H9BC109.5
H9AB—C9A—H9AC109.5H9BB—C9B—H9BC109.5
C4A—C10A—N2A112.0 (3)C4B—C10B—N2B112.0 (3)
C4A—C10A—H10A109.2C4B—C10B—H10C109.2
N2A—C10A—H10A109.2N2B—C10B—H10C109.2
C4A—C10A—H10B109.2C4B—C10B—H10D109.2
N2A—C10A—H10B109.2N2B—C10B—H10D109.2
H10A—C10A—H10B107.9H10C—C10B—H10D107.9
N2A—C11A—H11A109.5N2B—C11B—H11D109.5
N2A—C11A—H11B109.5N2B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
N2A—C11A—H11C109.5N2B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
N2A—C12A—H12A109.5N2B—C12B—H12D109.5
N2A—C12A—H12B109.5N2B—C12B—H12E109.5
H12A—C12A—H12B109.5H12D—C12B—H12E109.5
N2A—C12A—H12C109.5N2B—C12B—H12F109.5
H12A—C12A—H12C109.5H12D—C12B—H12F109.5
H12B—C12A—H12C109.5H12E—C12B—H12F109.5
C6A—C1A—C2A—C3A0.8 (6)C6B—C1B—C2B—C3B0.6 (6)
Pd1—C1A—C2A—C3A171.4 (3)Pd2—C1B—C2B—C3B171.2 (3)
C6A—C1A—C2A—C7A178.7 (4)C6B—C1B—C2B—C7B176.5 (3)
Pd1—C1A—C2A—C7A6.4 (5)Pd2—C1B—C2B—C7B5.9 (4)
C1A—C2A—C3A—C4A2.4 (6)C1B—C2B—C3B—C4B3.1 (6)
C7A—C2A—C3A—C4A175.3 (4)C7B—C2B—C3B—C4B173.7 (4)
C1A—C2A—C3A—Se1A175.3 (3)C1B—C2B—C3B—Se1B176.3 (3)
C7A—C2A—C3A—Se1A7.0 (5)C7B—C2B—C3B—Se1B6.8 (5)
C2A—C3A—C4A—C5A3.9 (6)C2B—C3B—C4B—C5B3.0 (6)
Se1A—C3A—C4A—C5A173.7 (3)Se1B—C3B—C4B—C5B176.4 (3)
C2A—C3A—C4A—C10A175.1 (4)C2B—C3B—C4B—C10B174.5 (4)
Se1A—C3A—C4A—C10A7.3 (5)Se1B—C3B—C4B—C10B6.1 (5)
C3A—C4A—C5A—C6A2.5 (6)C3B—C4B—C5B—C6B0.6 (6)
C10A—C4A—C5A—C6A176.6 (4)C10B—C4B—C5B—C6B177.1 (4)
C2A—C1A—C6A—C5A2.3 (6)C4B—C5B—C6B—C1B1.8 (6)
Pd1—C1A—C6A—C5A168.9 (3)C2B—C1B—C6B—C5B1.8 (6)
C4A—C5A—C6A—C1A0.6 (6)Pd2—C1B—C6B—C5B167.6 (3)
C3A—C2A—C7A—N1A145.8 (4)C9B—N1B—C7B—C2B78.0 (4)
C1A—C2A—C7A—N1A32.0 (5)C8B—N1B—C7B—C2B163.4 (4)
C8A—N1A—C7A—C2A164.8 (4)Pd2—N1B—C7B—C2B39.7 (4)
C9A—N1A—C7A—C2A76.2 (4)C3B—C2B—C7B—N1B145.9 (4)
Pd1—N1A—C7A—C2A40.1 (4)C1B—C2B—C7B—N1B31.1 (5)
C5A—C4A—C10A—N2A83.1 (4)C3B—C4B—C10B—N2B90.5 (5)
C3A—C4A—C10A—N2A95.9 (5)C5B—C4B—C10B—N2B87.1 (5)
C11A—N2A—C10A—C4A72.1 (4)C12B—N2B—C10B—C4B168.6 (4)
C12A—N2A—C10A—C4A164.0 (4)C11B—N2B—C10B—C4B68.3 (5)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2AA···Cl1Aii0.84 (2)2.45 (3)3.194 (4)149 (5)
N2A—H2AA···Cl2Aii0.84 (2)2.87 (4)3.488 (4)132 (4)
C8A—H8AC···Cl1A0.982.753.299 (5)116
C10A—H10B···Se1A0.992.753.270 (4)113
C11A—H11A···Cl2B0.982.913.659 (4)134
C11A—H11C···Cl2Aii0.982.883.379 (5)113
C12A—H12A···Cl1B0.982.823.692 (5)148
N2B—H2BA···Cl1Biii0.86 (2)2.61 (4)3.282 (4)135 (4)
N2B—H2BA···Cl2Biii0.86 (2)2.58 (3)3.306 (4)143 (4)
C8B—H8BB···Cl1B0.982.753.306 (5)117
C10B—H10C···Se1B0.992.763.239 (5)110
C10B—H10D···Cl1Aiv0.992.833.542 (4)130
C11B—H11D···Cl2Av0.982.693.587 (4)153
C12B—H12D···Cl1Av0.982.983.747 (5)136
C12B—H12F···Cl1Biii0.982.953.468 (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) top
Crystal data top
[Hg2(C12H19N2Se)Cl3]F(000) = 1400
Mr = 777.78Dx = 2.861 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 11.4366 (12) ÅCell parameters from 19623 reflections
b = 8.3635 (8) Åθ = 2.7–33.2°
c = 18.9894 (19) ŵ = 19.44 mm1
β = 96.230 (4)°T = 100 K
V = 1805.6 (3) Å3Plate, colourless
Z = 40.18 × 0.15 × 0.08 mm
Data collection top
Bruker Quest
diffractometer
9995 reflections with I > 2σ(I)
ω scansθmax = 33.2°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1717
Tmin = 0.307, Tmax = 0.746k = 012
18121 measured reflectionsl = 029
11191 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H-atom parameters constrained
S = 1.17 w = 1/[σ2(Fo2) + 163.3856P]
where P = (Fo2 + 2Fc2)/3
11191 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 4.41 e Å3
116 restraintsΔρmin = 4.77 e Å3
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. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Hg10.58521 (5)0.70850 (8)0.74456 (3)0.01472 (12)
Hg20.84222 (5)0.71587 (8)0.68071 (3)0.01328 (12)
Se10.66670 (13)0.53356 (18)0.65169 (8)0.0107 (3)
Cl10.6915 (4)0.9731 (4)0.68621 (19)0.0142 (6)
Cl20.5438 (4)0.8042 (6)0.8563 (2)0.0241 (9)
Cl31.0216 (3)0.8054 (6)0.7406 (2)0.0212 (8)
N10.3935 (13)0.7331 (18)0.6769 (7)0.016 (2)
N20.8741 (13)0.7528 (15)0.5567 (7)0.014 (2)
C10.5960 (13)0.6438 (18)0.5680 (8)0.012 (2)
C20.4735 (14)0.6746 (19)0.5606 (8)0.013 (2)
C30.4235 (16)0.7457 (18)0.4981 (8)0.016 (3)
H3A0.3415430.7676830.4927270.019*
C40.4893 (15)0.786 (2)0.4436 (8)0.017 (3)
H4A0.4527490.8334560.4014360.020*
C50.6085 (18)0.7550 (18)0.4511 (8)0.017 (3)
H5A0.6536820.7835960.4138540.020*
C60.6654 (14)0.6819 (17)0.5130 (7)0.011 (2)
C70.3949 (13)0.626 (2)0.6149 (8)0.014 (2)
H7A0.3135800.6177720.5913100.017*
H7B0.4188020.5181940.6323180.017*
C80.3049 (15)0.671 (2)0.7230 (10)0.023 (3)
H8A0.2265320.6720530.6963560.035*
H8B0.3047500.7395460.7649160.035*
H8C0.3255030.5616380.7378430.035*
C90.3672 (18)0.898 (2)0.6557 (10)0.023 (3)
H9A0.2870270.9041180.6317530.035*
H9B0.4230660.9337400.6233680.035*
H9C0.3738960.9664320.6977970.035*
C100.7933 (14)0.641 (2)0.5139 (8)0.014 (2)
H10A0.8062220.5316400.5330470.017*
H10B0.8138060.6407170.4646000.017*
C110.8541 (17)0.918 (2)0.5332 (9)0.019 (3)
H11A0.8649620.9260670.4828890.028*
H11B0.9102520.9880820.5608230.028*
H11C0.7737580.9494580.5402880.028*
C120.9964 (14)0.706 (2)0.5520 (9)0.020 (3)
H12A1.0179010.7321880.5047620.029*
H12B1.0052530.5912110.5604130.029*
H12C1.0479630.7647770.5877970.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.0112 (3)0.0221 (3)0.0114 (2)0.0009 (2)0.00382 (17)0.0022 (2)
Hg20.0094 (2)0.0196 (2)0.0112 (2)0.0019 (2)0.00269 (17)0.0017 (2)
Se10.0105 (6)0.0109 (6)0.0110 (6)0.0001 (5)0.0023 (5)0.0013 (5)
Cl10.0144 (16)0.0140 (15)0.0139 (15)0.0005 (14)0.0006 (12)0.0003 (12)
Cl20.029 (2)0.027 (2)0.0179 (16)0.0016 (18)0.0096 (15)0.0063 (16)
Cl30.0094 (16)0.028 (2)0.0261 (19)0.0010 (15)0.0020 (13)0.0119 (16)
N10.008 (5)0.020 (6)0.021 (5)0.003 (4)0.003 (4)0.002 (5)
N20.013 (5)0.014 (6)0.016 (5)0.002 (4)0.006 (4)0.004 (4)
C10.013 (5)0.009 (5)0.013 (5)0.000 (4)0.001 (4)0.001 (4)
C20.011 (5)0.012 (5)0.015 (4)0.000 (4)0.005 (4)0.002 (4)
C30.018 (6)0.013 (6)0.016 (5)0.001 (5)0.003 (4)0.002 (5)
C40.023 (6)0.013 (5)0.012 (5)0.001 (5)0.007 (4)0.007 (5)
C50.020 (6)0.015 (6)0.013 (5)0.006 (5)0.004 (4)0.003 (4)
C60.016 (5)0.011 (5)0.007 (4)0.003 (4)0.001 (4)0.002 (4)
C70.009 (5)0.014 (5)0.018 (5)0.001 (5)0.004 (4)0.002 (4)
C80.010 (7)0.027 (8)0.033 (8)0.003 (6)0.007 (6)0.003 (7)
C90.027 (9)0.015 (6)0.027 (8)0.005 (6)0.004 (7)0.000 (6)
C100.018 (5)0.014 (5)0.011 (5)0.000 (5)0.002 (4)0.003 (5)
C110.026 (8)0.016 (6)0.016 (6)0.001 (6)0.010 (6)0.007 (6)
C120.010 (6)0.023 (8)0.026 (7)0.000 (6)0.007 (5)0.003 (7)
Geometric parameters (Å, º) top
Hg1—Cl22.364 (4)C3—C41.39 (3)
Hg1—N12.427 (13)C3—H3A0.9500
Hg1—Se12.5449 (16)C4—C51.38 (3)
Hg1—Cl12.809 (4)C4—H4A0.9500
Hg1—Hg23.2995 (9)C5—C61.420 (19)
Hg1—Cl1i3.376 (4)C5—H5A0.9500
Hg2—Cl32.358 (4)C6—C101.50 (2)
Hg2—N22.442 (14)C7—H7A0.9900
Hg2—Se12.5334 (16)C7—H7B0.9900
Hg2—Cl12.766 (4)C8—H8A0.9800
Hg2—Cl1i3.297 (4)C8—H8B0.9800
Se1—C11.936 (14)C8—H8C0.9800
Se1—N13.619 (15)C9—H9A0.9800
Se1—N23.630 (15)C9—H9B0.9800
N1—C91.46 (2)C9—H9C0.9800
N1—C71.48 (2)C10—H10A0.9900
N1—C81.50 (2)C10—H10B0.9900
N2—C111.46 (2)C11—H11A0.9800
N2—C121.46 (2)C11—H11B0.9800
N2—C101.49 (2)C11—H11C0.9800
C1—C61.42 (2)C12—H12A0.9800
C1—C21.42 (2)C12—H12B0.9800
C2—C31.39 (2)C12—H12C0.9800
C2—C71.50 (2)
Cl2—Hg1—N1100.9 (4)C12—N2—Se1125.2 (10)
Cl2—Hg1—Se1160.22 (13)C10—N2—Se163.5 (8)
N1—Hg1—Se193.4 (4)Hg2—N2—Se144.2 (2)
Cl2—Hg1—Cl1102.99 (14)C6—C1—C2120.9 (13)
N1—Hg1—Cl197.4 (4)C6—C1—Se1119.6 (11)
Se1—Hg1—Cl188.45 (9)C2—C1—Se1119.3 (11)
Cl2—Hg1—Hg2126.64 (12)C3—C2—C1118.3 (16)
N1—Hg1—Hg2126.4 (4)C3—C2—C7118.8 (15)
Se1—Hg1—Hg249.33 (4)C1—C2—C7122.9 (13)
Cl1—Hg1—Hg253.11 (9)C4—C3—C2122.2 (17)
Cl2—Hg1—Cl1i93.71 (14)C4—C3—H3A118.9
N1—Hg1—Cl1i149.0 (4)C2—C3—H3A118.9
Se1—Hg1—Cl1i67.42 (7)C5—C4—C3119.3 (14)
Cl1—Hg1—Cl1i105.76 (5)C5—C4—H4A120.4
Hg2—Hg1—Cl1i59.17 (7)C3—C4—H4A120.4
Cl3—Hg2—N2102.2 (4)C4—C5—C6121.6 (18)
Cl3—Hg2—Se1157.47 (13)C4—C5—H5A119.2
N2—Hg2—Se193.7 (3)C6—C5—H5A119.2
Cl3—Hg2—Cl1104.37 (14)C1—C6—C5117.7 (16)
N2—Hg2—Cl195.6 (3)C1—C6—C10124.4 (12)
Se1—Hg2—Cl189.65 (9)C5—C6—C10117.8 (16)
Cl3—Hg2—Cl1i89.64 (14)N1—C7—C2116.4 (14)
N2—Hg2—Cl1i149.2 (3)N1—C7—H7A108.2
Se1—Hg2—Cl1i68.92 (7)C2—C7—H7A108.2
Cl1—Hg2—Cl1i108.96 (5)N1—C7—H7B108.2
Cl3—Hg2—Hg1126.29 (11)C2—C7—H7B108.2
N2—Hg2—Hg1126.1 (3)H7A—C7—H7B107.3
Se1—Hg2—Hg149.63 (4)N1—C8—H8A109.5
Cl1—Hg2—Hg154.33 (9)N1—C8—H8B109.5
Cl1i—Hg2—Hg161.57 (7)H8A—C8—H8B109.5
C1—Se1—Hg298.2 (5)N1—C8—H8C109.5
C1—Se1—Hg198.2 (5)H8A—C8—H8C109.5
Hg2—Se1—Hg181.04 (5)H8B—C8—H8C109.5
C1—Se1—N166.4 (5)N1—C9—H9A109.5
Hg2—Se1—N1111.6 (2)N1—C9—H9B109.5
Hg1—Se1—N142.0 (2)H9A—C9—H9B109.5
C1—Se1—N265.7 (5)N1—C9—H9C109.5
Hg2—Se1—N242.2 (2)H9A—C9—H9C109.5
Hg1—Se1—N2111.2 (2)H9B—C9—H9C109.5
N1—Se1—N2116.9 (3)N2—C10—C6114.2 (13)
Hg2—Cl1—Hg172.57 (9)N2—C10—H10A108.7
C9—N1—C7111.9 (13)C6—C10—H10A108.7
C9—N1—C8110.8 (15)N2—C10—H10B108.7
C7—N1—C8108.8 (14)C6—C10—H10B108.7
C9—N1—Hg1111.9 (11)H10A—C10—H10B107.6
C7—N1—Hg1106.4 (9)N2—C11—H11A109.5
C8—N1—Hg1106.8 (10)N2—C11—H11B109.5
C9—N1—Se1123.7 (12)H11A—C11—H11B109.5
C7—N1—Se162.1 (8)N2—C11—H11C109.5
C8—N1—Se1124.4 (10)H11A—C11—H11C109.5
Hg1—N1—Se144.6 (2)H11B—C11—H11C109.5
C11—N2—C12110.6 (14)N2—C12—H12A109.5
C11—N2—C10111.0 (12)N2—C12—H12B109.5
C12—N2—C10110.0 (13)H12A—C12—H12B109.5
C11—N2—Hg2112.3 (10)N2—C12—H12C109.5
C12—N2—Hg2105.6 (9)H12A—C12—H12C109.5
C10—N2—Hg2107.3 (9)H12B—C12—H12C109.5
C11—N2—Se1122.7 (11)
C6—C1—C2—C31 (2)C4—C5—C6—C10175.1 (15)
Se1—C1—C2—C3176.4 (12)C9—N1—C7—C253.9 (18)
C6—C1—C2—C7175.6 (14)C8—N1—C7—C2176.6 (13)
Se1—C1—C2—C70 (2)Hg1—N1—C7—C268.6 (13)
C1—C2—C3—C41 (2)Se1—N1—C7—C263.7 (11)
C7—C2—C3—C4176.2 (15)C3—C2—C7—N1102.2 (16)
C2—C3—C4—C50 (3)C1—C2—C7—N181.2 (19)
C3—C4—C5—C61 (2)C11—N2—C10—C655.2 (18)
C2—C1—C6—C51 (2)C12—N2—C10—C6177.9 (13)
Se1—C1—C6—C5176.7 (11)Hg2—N2—C10—C667.7 (13)
C2—C1—C6—C10174.7 (14)Se1—N2—C10—C661.8 (11)
Se1—C1—C6—C100.6 (19)C1—C6—C10—N280.2 (18)
C4—C5—C6—C11 (2)C5—C6—C10—N2103.7 (15)
Symmetry code: (i) x+3/2, y1/2, z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8A···Cl3ii0.982.813.479 (18)127
C8—H8C···Cl3i0.982.773.67 (2)154
C12—H12A···Cl2iii0.982.883.814 (18)159
C12—H12B···Cl2i0.982.963.84 (2)150
C12—H12C···Cl30.982.973.657 (18)128
Symmetry codes: (i) x+3/2, y1/2, z+3/2; (ii) x1, y, z; (iii) x+1/2, y+3/2, z1/2.
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds