The molecule of the title NC
NHCS pincer
N-heterocyclic carbene palladium(II) complex, [PdBr(C
21H
25N
3S)]Br, exhibits a slightly distorted square-planar coordination at the palladium(II) atom, with the five-membered chelate ring nearly planar. The six-membered chelate ring adopts an envelope conformation. Upon chelation, the sulfur atom becomes a stereogenic centre with an
RS configuration induced by the chiral carbon of the precursor imidazolium salt. There are intramolecular C—H

Br—Pd hydrogen bonds in the structure. The two interstitial Br atoms, as the counter-anion of the structure, are both located on crystallographic twofold axes and are connected to the complex cations
via C—H

·Br hydrogen bonds.
Supporting information
CCDC reference: 2312031
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.012 Å
- R factor = 0.030
- wR factor = 0.072
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT196_ALERT_1_B No TEMP record and _measurement_temperature .NE. 293 Degree
Alert level C
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.01176 Ang.
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 79 %
Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 293 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 293 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 2) 0.50 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd 3) 0.50 Check
PLAT480_ALERT_4_G Long H...A H-Bond Reported H16 ..BR3 . 3.11 Ang.
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C1 ..BR1 . 124 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C6 ..BR2 . 173 Degree
PLAT484_ALERT_4_G Round D-H..A Angle Rep for C10 ..BR3 . 144 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Pd1 (II) . 2.13 Info
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters 1 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
0 0 1,
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 16 Note
PLAT969_ALERT_5_G The 'Henn et al.' R-Factor-gap value ........... 1.91 Note
Predicted wR2: Based on SigI 2 3.79 or SHELX Weight 7.22
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 0 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
1 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
14 ALERT level G = General information/check it is not something unexpected
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
8 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
(
SC,
RS)-Bromido(
N-{4-methyl-1-[(4-methylphenyl)sulfanyl]pentan-2-yl}-
N'-(pyridin-2-yl)imidazol-2-ylidene)palladium(II) bromide
top
Crystal data top
[PdBr(C21H25N3S)]Br | F(000) = 1216 |
Mr = 617.72 | Dx = 1.785 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54184 Å |
a = 25.8993 (7) Å | Cell parameters from 8595 reflections |
b = 6.6206 (2) Å | θ = 4.5–70.1° |
c = 13.4938 (3) Å | µ = 11.52 mm−1 |
β = 96.425 (2)° | T = 293 K |
V = 2299.23 (12) Å3 | Plate, colourless |
Z = 4 | 0.14 × 0.1 × 0.03 mm |
Data collection top
Xcalibur, Eos, Gemini diffractometer | 3950 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source | 3693 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 16.2312 pixels mm-1 | θmax = 70.5°, θmin = 3.4° |
ω scans | h = −31→31 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2023) | k = −8→6 |
Tmin = 0.419, Tmax = 1.000 | l = −16→16 |
20069 measured reflections | |
Refinement top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.033P)2 + 2.7656P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.030 | (Δ/σ)max < 0.001 |
wR(F2) = 0.072 | Δρmax = 0.36 e Å−3 |
S = 1.04 | Δρmin = −0.38 e Å−3 |
3950 reflections | Extinction correction: SHELXL-2014/7 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
258 parameters | Extinction coefficient: 0.00034 (4) |
1 restraint | Absolute structure: Flack x determined using 1371 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.030 (7) |
Hydrogen site location: inferred from neighbouring sites | |
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. The H atoms on the carbons were positioned geometrically and
constrained to ride on their parent atoms. C—H bond distances were
constrained to 0.93 Å for aromatic and alkene C—H moieties, and to 0.98,
0.91 and 0.96 Å for aliphatic C—H, CH2 and CH3 moieties, respectively.
Methyl CH3 H atoms were allowed to rotate but not to tip to best fit the
experimental electron density. Uiso(H) values were set to a multiple
of Ueq(C) with 1.5 for CH3, and 1.2 for C—H and CH2 units,
respectively. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pd1 | 0.37598 (2) | 0.06095 (8) | 0.28758 (3) | 0.03701 (15) | |
S1 | 0.40637 (6) | −0.0902 (3) | 0.15555 (12) | 0.0381 (4) | |
N1 | 0.3574 (2) | 0.2356 (11) | 0.4079 (4) | 0.0443 (16) | |
N2 | 0.4255 (2) | 0.4165 (10) | 0.3607 (4) | 0.0413 (14) | |
N3 | 0.4680 (2) | 0.3203 (10) | 0.2419 (4) | 0.0381 (13) | |
C1 | 0.3187 (3) | 0.2026 (16) | 0.4635 (6) | 0.057 (2) | |
H1 | 0.2972 | 0.0912 | 0.4501 | 0.069* | |
C2 | 0.3100 (4) | 0.3329 (18) | 0.5414 (7) | 0.069 (3) | |
H2 | 0.2832 | 0.3085 | 0.5804 | 0.083* | |
C3 | 0.3414 (4) | 0.4954 (18) | 0.5587 (7) | 0.074 (3) | |
H3 | 0.3359 | 0.5840 | 0.6099 | 0.089* | |
C4 | 0.3813 (3) | 0.5318 (18) | 0.5021 (6) | 0.061 (2) | |
H4 | 0.4033 | 0.6422 | 0.5144 | 0.073* | |
C5 | 0.3873 (3) | 0.3975 (13) | 0.4263 (5) | 0.0450 (18) | |
C6 | 0.4650 (3) | 0.5562 (15) | 0.3556 (5) | 0.0478 (16) | |
H6 | 0.4719 | 0.6686 | 0.3963 | 0.057* | |
C7 | 0.4911 (3) | 0.4978 (13) | 0.2812 (6) | 0.049 (2) | |
H7 | 0.5195 | 0.5632 | 0.2593 | 0.059* | |
C8 | 0.4280 (2) | 0.2737 (13) | 0.2911 (5) | 0.0393 (16) | |
C9 | 0.4434 (2) | 0.1033 (12) | 0.0964 (5) | 0.0415 (18) | |
H9A | 0.4574 | 0.0439 | 0.0394 | 0.050* | |
H9B | 0.4199 | 0.2108 | 0.0720 | 0.050* | |
C10 | 0.4877 (3) | 0.1938 (11) | 0.1649 (5) | 0.0366 (15) | |
H10 | 0.5072 | 0.2821 | 0.1242 | 0.044* | |
C11 | 0.5255 (2) | 0.0360 (13) | 0.2122 (5) | 0.0397 (16) | |
H11A | 0.5325 | −0.0599 | 0.1610 | 0.048* | |
H11B | 0.5085 | −0.0373 | 0.2617 | 0.048* | |
C12 | 0.5777 (3) | 0.1161 (12) | 0.2623 (5) | 0.0441 (19) | |
H12 | 0.5707 | 0.2109 | 0.3150 | 0.053* | |
C13 | 0.6081 (3) | −0.0612 (16) | 0.3099 (7) | 0.065 (3) | |
H13A | 0.5892 | −0.1208 | 0.3598 | 0.097* | |
H13B | 0.6413 | −0.0150 | 0.3404 | 0.097* | |
H13C | 0.6132 | −0.1599 | 0.2598 | 0.097* | |
C14 | 0.6090 (3) | 0.2258 (18) | 0.1894 (7) | 0.072 (3) | |
H14A | 0.6092 | 0.1467 | 0.1298 | 0.108* | |
H14B | 0.6440 | 0.2448 | 0.2196 | 0.108* | |
H14C | 0.5935 | 0.3549 | 0.1729 | 0.108* | |
C15 | 0.3558 (3) | −0.1214 (13) | 0.0549 (5) | 0.0428 (18) | |
C16 | 0.3572 (3) | −0.2944 (13) | −0.0012 (6) | 0.0494 (19) | |
H16 | 0.3814 | −0.3949 | 0.0174 | 0.059* | |
C17 | 0.3221 (3) | −0.3171 (14) | −0.0853 (6) | 0.054 (2) | |
H17 | 0.3225 | −0.4353 | −0.1224 | 0.064* | |
C18 | 0.2862 (3) | −0.1665 (14) | −0.1157 (5) | 0.048 (2) | |
C19 | 0.2848 (3) | 0.0021 (14) | −0.0560 (5) | 0.051 (2) | |
H19 | 0.2601 | 0.1015 | −0.0734 | 0.061* | |
C20 | 0.3190 (3) | 0.0263 (14) | 0.0282 (5) | 0.049 (2) | |
H20 | 0.3176 | 0.1415 | 0.0672 | 0.059* | |
C21 | 0.2512 (3) | −0.1845 (17) | −0.2126 (6) | 0.067 (3) | |
H21A | 0.2684 | −0.1290 | −0.2659 | 0.101* | |
H21B | 0.2195 | −0.1116 | −0.2075 | 0.101* | |
H21C | 0.2433 | −0.3242 | −0.2261 | 0.101* | |
Br1 | 0.30979 (4) | −0.20451 (15) | 0.29589 (7) | 0.0603 (3) | |
Br2 | 0.5000 | 0.0140 (2) | 0.5000 | 0.0609 (4) | |
Br3 | 0.5000 | 0.61892 (17) | 0.0000 | 0.0480 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.0397 (2) | 0.0390 (3) | 0.0327 (2) | −0.0004 (2) | 0.00594 (15) | −0.0005 (2) |
S1 | 0.0391 (8) | 0.0388 (11) | 0.0362 (8) | 0.0001 (7) | 0.0032 (6) | −0.0042 (8) |
N1 | 0.050 (3) | 0.054 (5) | 0.030 (3) | 0.012 (3) | 0.009 (2) | −0.007 (3) |
N2 | 0.050 (3) | 0.036 (4) | 0.038 (3) | 0.007 (3) | 0.003 (2) | −0.007 (3) |
N3 | 0.042 (3) | 0.031 (4) | 0.042 (3) | −0.003 (3) | 0.006 (2) | 0.002 (3) |
C1 | 0.054 (4) | 0.073 (7) | 0.047 (4) | 0.009 (4) | 0.015 (3) | −0.002 (4) |
C2 | 0.063 (5) | 0.091 (9) | 0.055 (5) | 0.018 (5) | 0.019 (4) | 0.003 (5) |
C3 | 0.089 (7) | 0.087 (9) | 0.050 (4) | 0.020 (6) | 0.019 (4) | −0.017 (5) |
C4 | 0.071 (5) | 0.058 (7) | 0.054 (4) | 0.012 (5) | 0.010 (3) | −0.019 (5) |
C5 | 0.051 (4) | 0.043 (5) | 0.038 (4) | 0.010 (4) | −0.006 (3) | −0.007 (4) |
C6 | 0.061 (4) | 0.030 (4) | 0.050 (4) | −0.001 (4) | −0.001 (3) | −0.008 (4) |
C7 | 0.052 (4) | 0.038 (5) | 0.055 (4) | −0.011 (3) | 0.003 (3) | 0.000 (4) |
C8 | 0.042 (3) | 0.037 (5) | 0.036 (3) | 0.005 (3) | −0.003 (3) | −0.002 (3) |
C9 | 0.042 (3) | 0.047 (6) | 0.035 (3) | 0.001 (3) | 0.003 (2) | −0.001 (3) |
C10 | 0.045 (3) | 0.031 (4) | 0.034 (3) | −0.002 (3) | 0.008 (3) | −0.001 (3) |
C11 | 0.049 (3) | 0.032 (4) | 0.039 (3) | 0.002 (3) | 0.009 (2) | 0.000 (4) |
C12 | 0.043 (3) | 0.048 (6) | 0.041 (3) | −0.005 (3) | 0.004 (3) | −0.001 (3) |
C13 | 0.051 (4) | 0.073 (7) | 0.068 (5) | 0.007 (4) | −0.005 (4) | 0.010 (5) |
C14 | 0.051 (5) | 0.096 (9) | 0.069 (6) | −0.019 (5) | 0.006 (4) | 0.022 (6) |
C15 | 0.038 (3) | 0.051 (5) | 0.039 (3) | −0.001 (3) | 0.003 (3) | −0.009 (4) |
C16 | 0.047 (4) | 0.038 (5) | 0.062 (5) | 0.003 (3) | 0.001 (3) | −0.009 (4) |
C17 | 0.056 (4) | 0.051 (6) | 0.051 (4) | −0.001 (4) | −0.006 (3) | −0.020 (4) |
C18 | 0.036 (3) | 0.058 (6) | 0.048 (4) | −0.011 (3) | 0.004 (3) | −0.006 (4) |
C19 | 0.042 (4) | 0.060 (7) | 0.050 (4) | 0.007 (3) | 0.002 (3) | 0.000 (4) |
C20 | 0.051 (4) | 0.046 (6) | 0.051 (4) | 0.014 (4) | 0.004 (3) | −0.011 (4) |
C21 | 0.058 (5) | 0.079 (8) | 0.061 (5) | −0.003 (5) | −0.014 (4) | −0.006 (5) |
Br1 | 0.0612 (5) | 0.0547 (7) | 0.0674 (5) | −0.0142 (4) | 0.0173 (4) | 0.0042 (5) |
Br2 | 0.0953 (9) | 0.0421 (9) | 0.0444 (5) | 0.000 | 0.0037 (5) | 0.000 |
Br3 | 0.0607 (6) | 0.0392 (8) | 0.0460 (5) | 0.000 | 0.0141 (4) | 0.000 |
Geometric parameters (Å, º) top
Pd1—S1 | 2.2603 (17) | C10—H10 | 0.9800 |
Pd1—N1 | 2.093 (6) | C10—C11 | 1.522 (10) |
Pd1—C8 | 1.946 (8) | C11—H11A | 0.9700 |
Pd1—Br1 | 2.4663 (10) | C11—H11B | 0.9700 |
S1—C9 | 1.836 (7) | C11—C12 | 1.537 (9) |
S1—C15 | 1.789 (7) | C12—H12 | 0.9800 |
N1—C1 | 1.335 (9) | C12—C13 | 1.517 (11) |
N1—C5 | 1.330 (10) | C12—C14 | 1.527 (10) |
N2—C5 | 1.405 (9) | C13—H13A | 0.9600 |
N2—C6 | 1.387 (10) | C13—H13B | 0.9600 |
N2—C8 | 1.340 (9) | C13—H13C | 0.9600 |
N3—C7 | 1.396 (10) | C14—H14A | 0.9600 |
N3—C8 | 1.328 (9) | C14—H14B | 0.9600 |
N3—C10 | 1.470 (9) | C14—H14C | 0.9600 |
C1—H1 | 0.9300 | C15—C16 | 1.376 (11) |
C1—C2 | 1.397 (13) | C15—C20 | 1.384 (11) |
C2—H2 | 0.9300 | C16—H16 | 0.9300 |
C2—C3 | 1.354 (15) | C16—C17 | 1.380 (11) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C3—C4 | 1.373 (12) | C17—C18 | 1.393 (12) |
C4—H4 | 0.9300 | C18—C19 | 1.379 (11) |
C4—C5 | 1.376 (11) | C18—C21 | 1.511 (10) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.329 (10) | C19—C20 | 1.370 (10) |
C7—H7 | 0.9300 | C20—H20 | 0.9300 |
C9—H9A | 0.9700 | C21—H21A | 0.9600 |
C9—H9B | 0.9700 | C21—H21B | 0.9600 |
C9—C10 | 1.513 (9) | C21—H21C | 0.9600 |
| | | |
S1—Pd1—Br1 | 91.46 (5) | C9—C10—H10 | 107.3 |
N1—Pd1—S1 | 170.64 (19) | C9—C10—C11 | 113.1 (6) |
N1—Pd1—Br1 | 97.90 (19) | C11—C10—H10 | 107.3 |
C8—Pd1—S1 | 92.2 (2) | C10—C11—H11A | 108.3 |
C8—Pd1—N1 | 78.4 (3) | C10—C11—H11B | 108.3 |
C8—Pd1—Br1 | 175.9 (2) | C10—C11—C12 | 116.1 (7) |
C9—S1—Pd1 | 106.2 (2) | H11A—C11—H11B | 107.4 |
C15—S1—Pd1 | 111.0 (2) | C12—C11—H11A | 108.3 |
C15—S1—C9 | 97.2 (3) | C12—C11—H11B | 108.3 |
C1—N1—Pd1 | 126.7 (6) | C11—C12—H12 | 108.5 |
C5—N1—Pd1 | 114.3 (5) | C13—C12—C11 | 108.0 (7) |
C5—N1—C1 | 119.0 (7) | C13—C12—H12 | 108.5 |
C6—N2—C5 | 131.8 (6) | C13—C12—C14 | 110.6 (7) |
C8—N2—C5 | 118.1 (7) | C14—C12—C11 | 112.7 (6) |
C8—N2—C6 | 110.0 (6) | C14—C12—H12 | 108.5 |
C7—N3—C10 | 125.5 (6) | C12—C13—H13A | 109.5 |
C8—N3—C7 | 109.3 (6) | C12—C13—H13B | 109.5 |
C8—N3—C10 | 124.9 (6) | C12—C13—H13C | 109.5 |
N1—C1—H1 | 119.5 | H13A—C13—H13B | 109.5 |
N1—C1—C2 | 121.1 (9) | H13A—C13—H13C | 109.5 |
C2—C1—H1 | 119.5 | H13B—C13—H13C | 109.5 |
C1—C2—H2 | 120.8 | C12—C14—H14A | 109.5 |
C3—C2—C1 | 118.4 (8) | C12—C14—H14B | 109.5 |
C3—C2—H2 | 120.8 | C12—C14—H14C | 109.5 |
C2—C3—H3 | 119.4 | H14A—C14—H14B | 109.5 |
C2—C3—C4 | 121.3 (9) | H14A—C14—H14C | 109.5 |
C4—C3—H3 | 119.4 | H14B—C14—H14C | 109.5 |
C3—C4—H4 | 121.5 | C16—C15—S1 | 116.9 (6) |
C3—C4—C5 | 117.0 (10) | C16—C15—C20 | 120.2 (7) |
C5—C4—H4 | 121.5 | C20—C15—S1 | 122.7 (6) |
N1—C5—N2 | 113.0 (6) | C15—C16—H16 | 120.4 |
N1—C5—C4 | 123.2 (8) | C15—C16—C17 | 119.2 (8) |
C4—C5—N2 | 123.8 (8) | C17—C16—H16 | 120.4 |
N2—C6—H6 | 126.8 | C16—C17—H17 | 119.3 |
C7—C6—N2 | 106.5 (7) | C16—C17—C18 | 121.4 (8) |
C7—C6—H6 | 126.8 | C18—C17—H17 | 119.3 |
N3—C7—H7 | 126.3 | C17—C18—C21 | 121.0 (8) |
C6—C7—N3 | 107.4 (7) | C19—C18—C17 | 117.9 (7) |
C6—C7—H7 | 126.3 | C19—C18—C21 | 121.1 (8) |
N2—C8—Pd1 | 116.1 (5) | C18—C19—H19 | 119.3 |
N3—C8—Pd1 | 137.2 (6) | C20—C19—C18 | 121.5 (8) |
N3—C8—N2 | 106.7 (7) | C20—C19—H19 | 119.3 |
S1—C9—H9A | 108.7 | C15—C20—H20 | 120.1 |
S1—C9—H9B | 108.7 | C19—C20—C15 | 119.7 (8) |
H9A—C9—H9B | 107.6 | C19—C20—H20 | 120.1 |
C10—C9—S1 | 114.1 (5) | C18—C21—H21A | 109.5 |
C10—C9—H9A | 108.7 | C18—C21—H21B | 109.5 |
C10—C9—H9B | 108.7 | C18—C21—H21C | 109.5 |
N3—C10—C9 | 111.0 (5) | H21A—C21—H21B | 109.5 |
N3—C10—H10 | 107.3 | H21A—C21—H21C | 109.5 |
N3—C10—C11 | 110.6 (5) | H21B—C21—H21C | 109.5 |
| | | |
Pd1—S1—C9—C10 | 58.1 (5) | C7—N3—C8—Pd1 | −179.7 (6) |
Pd1—S1—C15—C16 | −143.9 (5) | C7—N3—C8—N2 | −0.4 (8) |
Pd1—S1—C15—C20 | 41.2 (7) | C7—N3—C10—C9 | −144.6 (7) |
Pd1—N1—C1—C2 | −179.1 (6) | C7—N3—C10—C11 | 89.0 (8) |
Pd1—N1—C5—N2 | −0.3 (8) | C8—N2—C5—N1 | −1.1 (9) |
Pd1—N1—C5—C4 | 179.8 (6) | C8—N2—C5—C4 | 178.8 (8) |
S1—C9—C10—N3 | −69.7 (7) | C8—N2—C6—C7 | 0.8 (9) |
S1—C9—C10—C11 | 55.2 (7) | C8—N3—C7—C6 | 0.9 (9) |
S1—C15—C16—C17 | −173.9 (6) | C8—N3—C10—C9 | 41.5 (9) |
S1—C15—C20—C19 | 173.0 (6) | C8—N3—C10—C11 | −84.8 (8) |
N1—C1—C2—C3 | 0.7 (14) | C9—S1—C15—C16 | 105.7 (6) |
N2—C6—C7—N3 | −1.0 (9) | C9—S1—C15—C20 | −69.3 (7) |
N3—C10—C11—C12 | −68.7 (7) | C9—C10—C11—C12 | 166.1 (5) |
C1—N1—C5—N2 | −178.3 (7) | C10—N3—C7—C6 | −173.7 (7) |
C1—N1—C5—C4 | 1.8 (12) | C10—N3—C8—Pd1 | −5.0 (11) |
C1—C2—C3—C4 | −0.5 (15) | C10—N3—C8—N2 | 174.3 (6) |
C2—C3—C4—C5 | 0.9 (15) | C10—C11—C12—C13 | 176.6 (6) |
C3—C4—C5—N1 | −1.6 (13) | C10—C11—C12—C14 | −60.9 (9) |
C3—C4—C5—N2 | 178.6 (8) | C15—S1—C9—C10 | 172.5 (5) |
C5—N1—C1—C2 | −1.3 (12) | C15—C16—C17—C18 | 1.5 (13) |
C5—N2—C6—C7 | 177.4 (7) | C16—C15—C20—C19 | −1.8 (12) |
C5—N2—C8—Pd1 | 2.0 (8) | C16—C17—C18—C19 | −3.5 (12) |
C5—N2—C8—N3 | −177.4 (6) | C16—C17—C18—C21 | 174.6 (8) |
C6—N2—C5—N1 | −177.5 (7) | C17—C18—C19—C20 | 2.9 (12) |
C6—N2—C5—C4 | 2.4 (13) | C18—C19—C20—C15 | −0.3 (12) |
C6—N2—C8—Pd1 | 179.2 (5) | C20—C15—C16—C17 | 1.2 (12) |
C6—N2—C8—N3 | −0.2 (8) | C21—C18—C19—C20 | −175.2 (8) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Br1 | 0.93 | 2.90 | 3.510 (10) | 124 |
C6—H6···Br2i | 0.93 | 2.74 | 3.661 (9) | 173 |
C10—H10···Br3 | 0.98 | 2.78 | 3.624 (7) | 144 |
C16—H16···Br3ii | 0.93 | 3.11 | 3.742 (7) | 127 |
Symmetry codes: (i) x, y+1, z; (ii) x, y−1, z. |