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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
CCDC references: 2018902; 2018901; 2018900
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
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) Å3 | Prism, orange |
Z = 4 | 0.33 × 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 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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.023 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.056 | H-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 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···N2Bi | 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:
C1',
N2'}bis[dichloridopalladium(II)] (15)
top
Crystal data top
[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) Å3 | Plate, brown |
Z = 8 | 0.26 × 0.25 × 0.08 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: mixed |
wR(F2) = 0.102 | H 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 parameters | Δρmax = 1.16 e Å−3 |
2 restraints | Δρmin = −1.42 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C3Bi | 1.937 (4) |
Se1A—C3Ai | 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—C3Ai | 95.8 (2) | C3Bi—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2AA···Cl1Aii | 0.84 (2) | 2.45 (3) | 3.194 (4) | 149 (5) |
N2A—H2AA···Cl2Aii | 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···Cl2Aii | 0.98 | 2.88 | 3.379 (5) | 113 |
C12A—H12A···Cl1B | 0.98 | 2.82 | 3.692 (5) | 148 |
N2B—H2BA···Cl1Biii | 0.86 (2) | 2.61 (4) | 3.282 (4) | 135 (4) |
N2B—H2BA···Cl2Biii | 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···Cl1Aiv | 0.99 | 2.83 | 3.542 (4) | 130 |
C11B—H11D···Cl2Av | 0.98 | 2.69 | 3.587 (4) | 153 |
C12B—H12D···Cl1Av | 0.98 | 2.98 | 3.747 (5) | 136 |
C12B—H12F···Cl1Biii | 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)
top
Crystal data top
[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) Å3 | Plate, colourless |
Z = 4 | 0.18 × 0.15 × 0.08 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-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 parameters | Δρmax = 4.41 e Å−3 |
116 restraints | Δρmin = −4.77 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—Cl1i | 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—Cl1i | 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—Cl1i | 93.71 (14) | C4—C3—H3A | 118.9 |
N1—Hg1—Cl1i | 149.0 (4) | C2—C3—H3A | 118.9 |
Se1—Hg1—Cl1i | 67.42 (7) | C5—C4—C3 | 119.3 (14) |
Cl1—Hg1—Cl1i | 105.76 (5) | C5—C4—H4A | 120.4 |
Hg2—Hg1—Cl1i | 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—Cl1i | 89.64 (14) | N1—C7—C2 | 116.4 (14) |
N2—Hg2—Cl1i | 149.2 (3) | N1—C7—H7A | 108.2 |
Se1—Hg2—Cl1i | 68.92 (7) | C2—C7—H7A | 108.2 |
Cl1—Hg2—Cl1i | 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 |
Cl1i—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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···Cl3ii | 0.98 | 2.81 | 3.479 (18) | 127 |
C8—H8C···Cl3i | 0.98 | 2.77 | 3.67 (2) | 154 |
C12—H12A···Cl2iii | 0.98 | 2.88 | 3.814 (18) | 159 |
C12—H12B···Cl2i | 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. |
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