The structure of the title compound, [PdCl
2(C
26H
27N
2P)]·C
4H
10O, was determined at 150 K. The palladium center is in a square-planar coordination geometry. A non-classical hydrogen bond (C—H
O) exists between the palladium complex and solvent molecule. The two chloride ligands are also involved in weak non-classical hydrogen bonds linking two neighboring molecules.
Supporting information
CCDC reference: 252785
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.031
- wR factor = 0.080
- Data-to-parameter ratio = 20.3
checkCIF/PLATON results
No syntax errors found
Alert level A
DIFF020_ALERT_1_A _diffrn_standards_interval_count and
_diffrn_standards_interval_time are missing. Number of measurements
between standards or time (min) between standards.
DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing
Percentage decrease in standards intensity.
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.82 Ratio
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. CL2 .. 2.93 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5A .. CL1 .. 2.90 Ang.
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
3 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 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
0 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Dichloro{1-[2-(diphenylphosphino-
κP)ethyl]-1,3-dihydro-3-(2,4,6-
trimethylphenyl)-2
H-imidazol-2-ylidene-
κC}palladium(II) diethyl
ether solvate
top
Crystal data top
[PdCl2(C26H27N2P)].C4H10O | F(000) = 1336 |
Mr = 649.89 | Dx = 1.432 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 926 reflections |
a = 13.046 (5) Å | θ = 2.9–26.9° |
b = 14.242 (6) Å | µ = 0.87 mm−1 |
c = 16.289 (7) Å | T = 150 K |
β = 95.01 (4)° | Plate, colorless |
V = 3015 (2) Å3 | 0.36 × 0.30 × 0.06 mm |
Z = 4 | |
Data collection top
Bruker SMART 1000 diffractometer | 6845 independent reflections |
Radiation source: fine-focus sealed tube | 5422 reflections with I > 2σ |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS, Sheldrick, 2002) | h = −16→16 |
Tmin = 0.745, Tmax = 0.950 | k = −18→18 |
29264 measured reflections | l = −20→20 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.080 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0382P)2 + 2.9149P] where P = (Fo2 + 2Fc2)/3 |
6845 reflections | (Δ/σ)max = 0.002 |
337 parameters | Δρmax = 0.77 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Pd1 | 0.665252 (14) | 0.299890 (13) | 0.586263 (11) | 0.01938 (6) | |
Cl1 | 0.55560 (5) | 0.26500 (5) | 0.46796 (4) | 0.02935 (15) | |
Cl2 | 0.80903 (5) | 0.31548 (5) | 0.50780 (4) | 0.02943 (15) | |
O1 | 1.01978 (19) | 0.59153 (19) | 0.83998 (16) | 0.0575 (7) | |
N1 | 0.75297 (16) | 0.29443 (14) | 0.76301 (13) | 0.0228 (4) | |
N2 | 0.80588 (16) | 0.41746 (14) | 0.70340 (13) | 0.0223 (4) | |
P1 | 0.53425 (5) | 0.26267 (5) | 0.65918 (4) | 0.02155 (14) | |
C1 | 0.74666 (19) | 0.34006 (17) | 0.68978 (15) | 0.0209 (5) | |
C2 | 0.8164 (2) | 0.34127 (19) | 0.82175 (16) | 0.0271 (6) | |
H2A | 0.8330 | 0.3226 | 0.8773 | 0.033* | |
C3 | 0.8501 (2) | 0.41856 (19) | 0.78480 (16) | 0.0271 (6) | |
H3A | 0.8953 | 0.4650 | 0.8093 | 0.033* | |
C4 | 0.6883 (2) | 0.21399 (18) | 0.78122 (16) | 0.0276 (6) | |
H4A | 0.7051 | 0.1936 | 0.8389 | 0.033* | |
H4B | 0.7019 | 0.1609 | 0.7445 | 0.033* | |
C5 | 0.5755 (2) | 0.2420 (2) | 0.76832 (16) | 0.0280 (6) | |
H5A | 0.5645 | 0.2999 | 0.8001 | 0.034* | |
H5B | 0.5327 | 0.1917 | 0.7896 | 0.034* | |
C6 | 0.8203 (2) | 0.49480 (17) | 0.64764 (15) | 0.0230 (5) | |
C7 | 0.7394 (2) | 0.55752 (18) | 0.62930 (16) | 0.0274 (6) | |
C8 | 0.7580 (2) | 0.63418 (19) | 0.57958 (17) | 0.0313 (6) | |
H8A | 0.7039 | 0.6775 | 0.5655 | 0.038* | |
C9 | 0.8533 (2) | 0.6490 (2) | 0.54994 (18) | 0.0353 (7) | |
C10 | 0.9316 (2) | 0.58568 (19) | 0.57066 (17) | 0.0319 (6) | |
H10A | 0.9972 | 0.5960 | 0.5511 | 0.038* | |
C11 | 0.9173 (2) | 0.50728 (18) | 0.61938 (16) | 0.0260 (5) | |
C12 | 0.6364 (2) | 0.5466 (2) | 0.66253 (19) | 0.0362 (7) | |
H12A | 0.5896 | 0.5954 | 0.6390 | 0.054* | |
H12B | 0.6442 | 0.5528 | 0.7227 | 0.054* | |
H12C | 0.6081 | 0.4846 | 0.6476 | 0.054* | |
C13 | 1.0037 (2) | 0.4394 (2) | 0.64114 (18) | 0.0331 (6) | |
H13A | 1.0598 | 0.4516 | 0.6064 | 0.050* | |
H13B | 0.9787 | 0.3751 | 0.6321 | 0.050* | |
H13C | 1.0288 | 0.4475 | 0.6992 | 0.050* | |
C14 | 0.8716 (3) | 0.7319 (3) | 0.4949 (2) | 0.0588 (10) | |
H14A | 0.9452 | 0.7467 | 0.4987 | 0.088* | |
H14B | 0.8333 | 0.7865 | 0.5126 | 0.088* | |
H14C | 0.8480 | 0.7164 | 0.4378 | 0.088* | |
C15 | 0.4316 (2) | 0.34856 (18) | 0.65952 (17) | 0.0285 (6) | |
C16 | 0.3671 (2) | 0.3499 (2) | 0.7233 (2) | 0.0429 (8) | |
H16A | 0.3770 | 0.3060 | 0.7672 | 0.051* | |
C17 | 0.2882 (3) | 0.4155 (3) | 0.7228 (3) | 0.0539 (10) | |
H17A | 0.2435 | 0.4158 | 0.7658 | 0.065* | |
C18 | 0.2748 (2) | 0.4802 (2) | 0.6598 (3) | 0.0528 (10) | |
H18A | 0.2214 | 0.5255 | 0.6600 | 0.063* | |
C19 | 0.3382 (3) | 0.4796 (2) | 0.5969 (2) | 0.0472 (9) | |
H19A | 0.3285 | 0.5245 | 0.5538 | 0.057* | |
C20 | 0.4165 (2) | 0.41347 (19) | 0.59580 (19) | 0.0363 (7) | |
H20A | 0.4596 | 0.4126 | 0.5517 | 0.044* | |
C21 | 0.4734 (2) | 0.15150 (17) | 0.62760 (15) | 0.0241 (5) | |
C22 | 0.5338 (2) | 0.0727 (2) | 0.62040 (18) | 0.0339 (6) | |
H22A | 0.6066 | 0.0778 | 0.6288 | 0.041* | |
C23 | 0.4888 (3) | −0.0141 (2) | 0.60091 (19) | 0.0391 (7) | |
H23A | 0.5309 | −0.0679 | 0.5962 | 0.047* | |
C24 | 0.3841 (3) | −0.0221 (2) | 0.58862 (18) | 0.0382 (7) | |
H24A | 0.3535 | −0.0814 | 0.5754 | 0.046* | |
C25 | 0.3233 (3) | 0.0559 (2) | 0.5955 (2) | 0.0428 (8) | |
H25A | 0.2506 | 0.0502 | 0.5872 | 0.051* | |
C26 | 0.3676 (2) | 0.1433 (2) | 0.61462 (19) | 0.0355 (7) | |
H26A | 0.3252 | 0.1970 | 0.6187 | 0.043* | |
C27 | 1.0190 (3) | 0.6758 (3) | 0.7933 (3) | 0.0676 (12) | |
H27A | 1.0543 | 0.6654 | 0.7427 | 0.081* | |
H27B | 1.0565 | 0.7256 | 0.8260 | 0.081* | |
C28 | 0.9116 (3) | 0.7060 (3) | 0.7709 (3) | 0.0635 (11) | |
H28A | 0.9116 | 0.7641 | 0.7386 | 0.095* | |
H28B | 0.8773 | 0.7171 | 0.8212 | 0.095* | |
H28C | 0.8750 | 0.6568 | 0.7381 | 0.095* | |
C29 | 1.1206 (3) | 0.5652 (3) | 0.8705 (3) | 0.0734 (13) | |
H29A | 1.1502 | 0.6138 | 0.9091 | 0.088* | |
H29B | 1.1648 | 0.5603 | 0.8243 | 0.088* | |
C30 | 1.1179 (4) | 0.4735 (4) | 0.9136 (4) | 0.113 (2) | |
H30A | 1.1878 | 0.4559 | 0.9350 | 0.169* | |
H30B | 1.0898 | 0.4254 | 0.8749 | 0.169* | |
H30C | 1.0743 | 0.4787 | 0.9594 | 0.169* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Pd1 | 0.02417 (10) | 0.02036 (10) | 0.01378 (10) | 0.00013 (8) | 0.00260 (7) | 0.00053 (7) |
Cl1 | 0.0381 (4) | 0.0327 (3) | 0.0166 (3) | −0.0059 (3) | −0.0007 (3) | −0.0015 (2) |
Cl2 | 0.0289 (3) | 0.0389 (4) | 0.0215 (3) | −0.0007 (3) | 0.0082 (2) | −0.0017 (3) |
O1 | 0.0495 (15) | 0.0637 (16) | 0.0580 (16) | −0.0149 (13) | −0.0036 (12) | −0.0034 (13) |
N1 | 0.0251 (11) | 0.0262 (11) | 0.0171 (10) | 0.0023 (9) | 0.0017 (8) | 0.0020 (8) |
N2 | 0.0216 (11) | 0.0258 (11) | 0.0192 (11) | −0.0004 (8) | 0.0006 (8) | 0.0005 (8) |
P1 | 0.0238 (3) | 0.0228 (3) | 0.0182 (3) | −0.0014 (3) | 0.0029 (2) | −0.0007 (2) |
C1 | 0.0222 (12) | 0.0241 (12) | 0.0167 (12) | 0.0028 (10) | 0.0041 (9) | 0.0004 (9) |
C2 | 0.0281 (14) | 0.0333 (14) | 0.0190 (13) | 0.0024 (11) | −0.0027 (10) | 0.0004 (11) |
C3 | 0.0251 (13) | 0.0323 (14) | 0.0232 (13) | −0.0010 (11) | −0.0019 (10) | −0.0033 (11) |
C4 | 0.0362 (15) | 0.0266 (13) | 0.0201 (13) | −0.0019 (11) | 0.0022 (11) | 0.0049 (10) |
C5 | 0.0312 (14) | 0.0345 (14) | 0.0188 (13) | −0.0057 (11) | 0.0047 (11) | −0.0006 (11) |
C6 | 0.0262 (13) | 0.0220 (12) | 0.0206 (13) | −0.0025 (10) | 0.0006 (10) | −0.0013 (10) |
C7 | 0.0300 (14) | 0.0281 (13) | 0.0232 (13) | 0.0011 (11) | −0.0025 (11) | −0.0042 (11) |
C8 | 0.0378 (16) | 0.0258 (13) | 0.0294 (15) | 0.0066 (12) | −0.0025 (12) | 0.0002 (11) |
C9 | 0.0487 (18) | 0.0289 (14) | 0.0287 (15) | −0.0004 (13) | 0.0055 (13) | 0.0031 (12) |
C10 | 0.0354 (16) | 0.0327 (15) | 0.0283 (15) | −0.0040 (12) | 0.0070 (12) | 0.0021 (12) |
C11 | 0.0262 (14) | 0.0279 (13) | 0.0237 (13) | −0.0006 (11) | 0.0005 (10) | −0.0015 (10) |
C12 | 0.0289 (15) | 0.0359 (15) | 0.0440 (18) | 0.0079 (12) | 0.0037 (13) | −0.0001 (13) |
C13 | 0.0232 (14) | 0.0367 (15) | 0.0397 (17) | 0.0006 (11) | 0.0044 (12) | 0.0045 (13) |
C14 | 0.076 (3) | 0.0449 (19) | 0.059 (2) | 0.0109 (19) | 0.023 (2) | 0.0221 (18) |
C15 | 0.0257 (14) | 0.0260 (13) | 0.0335 (15) | −0.0015 (11) | 0.0014 (11) | −0.0101 (11) |
C16 | 0.0357 (17) | 0.0428 (18) | 0.052 (2) | −0.0013 (14) | 0.0145 (15) | −0.0080 (15) |
C17 | 0.0329 (18) | 0.053 (2) | 0.078 (3) | −0.0020 (16) | 0.0194 (17) | −0.027 (2) |
C18 | 0.0266 (17) | 0.0365 (18) | 0.093 (3) | 0.0028 (13) | −0.0057 (18) | −0.0269 (19) |
C19 | 0.0405 (19) | 0.0299 (16) | 0.067 (2) | 0.0053 (13) | −0.0172 (17) | −0.0087 (15) |
C20 | 0.0377 (17) | 0.0273 (14) | 0.0422 (18) | 0.0033 (12) | −0.0058 (13) | −0.0066 (12) |
C21 | 0.0327 (14) | 0.0237 (13) | 0.0161 (12) | −0.0057 (10) | 0.0028 (10) | 0.0012 (10) |
C22 | 0.0333 (16) | 0.0317 (15) | 0.0371 (17) | 0.0000 (12) | 0.0050 (12) | −0.0022 (12) |
C23 | 0.052 (2) | 0.0249 (14) | 0.0402 (18) | 0.0010 (13) | 0.0042 (15) | −0.0029 (12) |
C24 | 0.055 (2) | 0.0294 (15) | 0.0302 (16) | −0.0129 (14) | 0.0035 (14) | −0.0005 (12) |
C25 | 0.0372 (17) | 0.0420 (18) | 0.0480 (19) | −0.0106 (14) | −0.0032 (14) | −0.0021 (15) |
C26 | 0.0343 (16) | 0.0295 (14) | 0.0421 (18) | −0.0025 (12) | −0.0014 (13) | −0.0005 (12) |
C27 | 0.058 (3) | 0.040 (2) | 0.106 (4) | −0.0155 (18) | 0.017 (2) | −0.022 (2) |
C28 | 0.073 (3) | 0.055 (2) | 0.060 (3) | −0.007 (2) | −0.005 (2) | −0.0254 (19) |
C29 | 0.055 (3) | 0.075 (3) | 0.089 (3) | −0.008 (2) | −0.003 (2) | −0.020 (3) |
C30 | 0.100 (4) | 0.139 (5) | 0.094 (4) | −0.004 (4) | −0.025 (3) | 0.041 (4) |
Geometric parameters (Å, º) top
Pd1—C1 | 1.996 (3) | C13—H13C | 0.9800 |
Pd1—P1 | 2.2287 (11) | C14—H14A | 0.9800 |
Pd1—Cl1 | 2.3505 (13) | C14—H14B | 0.9800 |
Pd1—Cl2 | 2.3705 (12) | C14—H14C | 0.9800 |
O1—C29 | 1.416 (5) | C15—C20 | 1.391 (4) |
O1—C27 | 1.421 (5) | C15—C16 | 1.394 (4) |
N1—C1 | 1.354 (3) | C16—C17 | 1.389 (5) |
N1—C2 | 1.381 (3) | C16—H16A | 0.9500 |
N1—C4 | 1.468 (3) | C17—C18 | 1.379 (5) |
N2—C1 | 1.353 (3) | C17—H17A | 0.9500 |
N2—C3 | 1.399 (3) | C18—C19 | 1.372 (5) |
N2—C6 | 1.450 (3) | C18—H18A | 0.9500 |
P1—C15 | 1.814 (3) | C19—C20 | 1.391 (4) |
P1—C21 | 1.825 (3) | C19—H19A | 0.9500 |
P1—C5 | 1.836 (3) | C20—H20A | 0.9500 |
C2—C3 | 1.347 (4) | C21—C22 | 1.382 (4) |
C2—H2A | 0.9500 | C21—C26 | 1.383 (4) |
C3—H3A | 0.9500 | C22—C23 | 1.394 (4) |
C4—C5 | 1.522 (4) | C22—H22A | 0.9500 |
C4—H4A | 0.9900 | C23—C24 | 1.367 (4) |
C4—H4B | 0.9900 | C23—H23A | 0.9500 |
C5—H5A | 0.9900 | C24—C25 | 1.375 (5) |
C5—H5B | 0.9900 | C24—H24A | 0.9500 |
C6—C7 | 1.395 (4) | C25—C26 | 1.396 (4) |
C6—C11 | 1.395 (4) | C25—H25A | 0.9500 |
C7—C8 | 1.393 (4) | C26—H26A | 0.9500 |
C7—C12 | 1.500 (4) | C27—C28 | 1.480 (5) |
C8—C9 | 1.390 (4) | C27—H27A | 0.9900 |
C8—H8A | 0.9500 | C27—H27B | 0.9900 |
C9—C10 | 1.382 (4) | C28—H28A | 0.9800 |
C9—C14 | 1.514 (4) | C28—H28B | 0.9800 |
C10—C11 | 1.392 (4) | C28—H28C | 0.9800 |
C10—H10A | 0.9500 | C29—C30 | 1.485 (7) |
C11—C13 | 1.503 (4) | C29—H29A | 0.9900 |
C12—H12A | 0.9800 | C29—H29B | 0.9900 |
C12—H12B | 0.9800 | C30—H30A | 0.9800 |
C12—H12C | 0.9800 | C30—H30B | 0.9800 |
C13—H13A | 0.9800 | C30—H30C | 0.9800 |
C13—H13B | 0.9800 | | |
| | | |
C1—Pd1—P1 | 89.67 (8) | H13A—C13—H13C | 109.5 |
C1—Pd1—Cl1 | 173.60 (7) | H13B—C13—H13C | 109.5 |
P1—Pd1—Cl1 | 86.93 (4) | C9—C14—H14A | 109.5 |
C1—Pd1—Cl2 | 92.34 (8) | C9—C14—H14B | 109.5 |
P1—Pd1—Cl2 | 171.60 (3) | H14A—C14—H14B | 109.5 |
Cl1—Pd1—Cl2 | 91.80 (4) | C9—C14—H14C | 109.5 |
C29—O1—C27 | 112.0 (3) | H14A—C14—H14C | 109.5 |
C1—N1—C2 | 111.4 (2) | H14B—C14—H14C | 109.5 |
C1—N1—C4 | 124.1 (2) | C20—C15—C16 | 119.5 (3) |
C2—N1—C4 | 123.8 (2) | C20—C15—P1 | 120.1 (2) |
C1—N2—C3 | 110.3 (2) | C16—C15—P1 | 120.4 (2) |
C1—N2—C6 | 128.3 (2) | C17—C16—C15 | 120.0 (3) |
C3—N2—C6 | 121.3 (2) | C17—C16—H16A | 120.0 |
C15—P1—C21 | 106.43 (13) | C15—C16—H16A | 120.0 |
C15—P1—C5 | 105.01 (13) | C18—C17—C16 | 120.0 (3) |
C21—P1—C5 | 102.57 (12) | C18—C17—H17A | 120.0 |
C15—P1—Pd1 | 116.23 (10) | C16—C17—H17A | 120.0 |
C21—P1—Pd1 | 113.02 (9) | C19—C18—C17 | 120.4 (3) |
C5—P1—Pd1 | 112.37 (9) | C19—C18—H18A | 119.8 |
N2—C1—N1 | 104.9 (2) | C17—C18—H18A | 119.8 |
N2—C1—Pd1 | 128.74 (18) | C18—C19—C20 | 120.3 (3) |
N1—C1—Pd1 | 126.38 (18) | C18—C19—H19A | 119.8 |
C3—C2—N1 | 106.5 (2) | C20—C19—H19A | 119.8 |
C3—C2—H2A | 126.7 | C19—C20—C15 | 119.8 (3) |
N1—C2—H2A | 126.7 | C19—C20—H20A | 120.1 |
C2—C3—N2 | 106.9 (2) | C15—C20—H20A | 120.1 |
C2—C3—H3A | 126.5 | C22—C21—C26 | 119.2 (2) |
N2—C3—H3A | 126.5 | C22—C21—P1 | 119.4 (2) |
N1—C4—C5 | 109.4 (2) | C26—C21—P1 | 121.3 (2) |
N1—C4—H4A | 109.8 | C21—C22—C23 | 120.5 (3) |
C5—C4—H4A | 109.8 | C21—C22—H22A | 119.8 |
N1—C4—H4B | 109.8 | C23—C22—H22A | 119.8 |
C5—C4—H4B | 109.8 | C24—C23—C22 | 120.2 (3) |
H4A—C4—H4B | 108.2 | C24—C23—H23A | 119.9 |
C4—C5—P1 | 111.96 (18) | C22—C23—H23A | 119.9 |
C4—C5—H5A | 109.2 | C23—C24—C25 | 119.8 (3) |
P1—C5—H5A | 109.2 | C23—C24—H24A | 120.1 |
C4—C5—H5B | 109.2 | C25—C24—H24A | 120.1 |
P1—C5—H5B | 109.2 | C24—C25—C26 | 120.6 (3) |
H5A—C5—H5B | 107.9 | C24—C25—H25A | 119.7 |
C7—C6—C11 | 122.6 (2) | C26—C25—H25A | 119.7 |
C7—C6—N2 | 118.9 (2) | C21—C26—C25 | 119.8 (3) |
C11—C6—N2 | 118.3 (2) | C21—C26—H26A | 120.1 |
C8—C7—C6 | 117.4 (3) | C25—C26—H26A | 120.1 |
C8—C7—C12 | 119.8 (2) | O1—C27—C28 | 109.9 (3) |
C6—C7—C12 | 122.8 (2) | O1—C27—H27A | 109.7 |
C9—C8—C7 | 121.8 (3) | C28—C27—H27A | 109.7 |
C9—C8—H8A | 119.1 | O1—C27—H27B | 109.7 |
C7—C8—H8A | 119.1 | C28—C27—H27B | 109.7 |
C10—C9—C8 | 118.8 (3) | H27A—C27—H27B | 108.2 |
C10—C9—C14 | 120.2 (3) | C27—C28—H28A | 109.5 |
C8—C9—C14 | 121.1 (3) | C27—C28—H28B | 109.5 |
C9—C10—C11 | 122.0 (3) | H28A—C28—H28B | 109.5 |
C9—C10—H10A | 119.0 | C27—C28—H28C | 109.5 |
C11—C10—H10A | 119.0 | H28A—C28—H28C | 109.5 |
C10—C11—C6 | 117.5 (2) | H28B—C28—H28C | 109.5 |
C10—C11—C13 | 121.0 (3) | O1—C29—C30 | 109.8 (4) |
C6—C11—C13 | 121.5 (2) | O1—C29—H29A | 109.7 |
C7—C12—H12A | 109.5 | C30—C29—H29A | 109.7 |
C7—C12—H12B | 109.5 | O1—C29—H29B | 109.7 |
H12A—C12—H12B | 109.5 | C30—C29—H29B | 109.7 |
C7—C12—H12C | 109.5 | H29A—C29—H29B | 108.2 |
H12A—C12—H12C | 109.5 | C29—C30—H30A | 109.5 |
H12B—C12—H12C | 109.5 | C29—C30—H30B | 109.5 |
C11—C13—H13A | 109.5 | H30A—C30—H30B | 109.5 |
C11—C13—H13B | 109.5 | C29—C30—H30C | 109.5 |
H13A—C13—H13B | 109.5 | H30A—C30—H30C | 109.5 |
C11—C13—H13C | 109.5 | H30B—C30—H30C | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2A···Cl2i | 0.95 | 2.93 | 3.772 (3) | 148 |
C3—H3A···O1 | 0.95 | 2.45 | 3.381 (4) | 167 |
C5—H5A···Cl1i | 0.99 | 2.90 | 3.286 (3) | 104 |
Symmetry code: (i) x, −y+1/2, z+1/2. |