The title compound, [Zr2(C5H5)4(C16H15PS)2]·2CH2Cl2, was prepared by insertion of diphosphinoacetylene into the Zr—C bond of the transient (η2-thioaldehyde)zirconocene formed by treatment of Cp2ZrMe2 with one equivalent of ethanediol. The sulfonium zirconocenate complex exhibits a centrosymmetric sulfur-bridged dimeric structure.
Supporting information
CCDC reference: 234817
Key indicators
- Single-crystal X-ray study
- T = 110 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.092
- Data-to-parameter ratio = 18.3
checkCIF/PLATON results
No syntax errors found
Alert level C
ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10
Absorption corrections should be applied.
Tmin and Tmax expected: 0.683 0.816
RT(exp) = 1.195
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) = 1.19
PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . C2
PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . H2
PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . C3
PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . H3
PLAT070_ALERT_1_C Duplicate or Troublesome Atomic Label on Input . C4
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H25 .. H41 = 1.84 Ang.
PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CT1
ZR CT1
PLAT711_ALERT_1_C BOND Unknown or Inconsistent Label .......... CT2
ZR CT2
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT1
CT1 ZR CT2
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT1
CT1 ZR S
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT1
CT1 ZR S
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT1
CT1 ZR C1
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT2
CT2 ZR S
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT2
CT2 ZR S
PLAT712_ALERT_1_C ANGLE Unknown or Inconsistent Label .......... CT2
CT2 ZR C1
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.50 Deg.
C3 -S -C3* 1.555 1.555 1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 26.60 Deg.
C2 -C1 -C2* 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
24 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
15 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: KappaCCD Server Software (Nonius, 1997); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997); data reduction: DENZO–SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 1999).
Crystal data top
[Zr2(C5H5)4(C16H15PS)2]·2CH2Cl2 | F(000) = 1176 |
Mr = 1153.29 | Dx = 1.532 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2116 (5) Å | Cell parameters from 1776 reflections |
b = 12.4090 (6) Å | θ = 1.0–27.5° |
c = 17.2983 (9) Å | µ = 0.82 mm−1 |
β = 107.526 (2)° | T = 110 K |
V = 2499.6 (2) Å3 | Prism, colorless |
Z = 2 | 0.50 × 0.40 × 0.25 mm |
Data collection top
KappaCCD diffractometer | Rint = 0.043 |
φ scans (κ = 0) + additional ω scans | θmax = 27.4°, θmin = 2.9° |
9529 measured reflections | h = −11→15 |
5521 independent reflections | k = −16→9 |
4454 reflections with I > 2σ(I) | l = −22→13 |
Refinement top
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0361P)2 + 2.0399P] where P = (Fo2 + 2Fc2)/3 |
5521 reflections | (Δ/σ)max = 0.001 |
302 parameters | Δρmax = 0.75 e Å−3 |
0 restraints | Δρmin = −0.91 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zr | 0.19357 (2) | −0.003236 (18) | 0.013559 (14) | 0.01232 (8) | |
P | 0.41401 (6) | 0.18619 (6) | 0.12638 (4) | 0.01934 (16) | |
S | 0.02379 (6) | 0.08115 (5) | 0.05544 (4) | 0.01817 (15) | |
C1 | 0.2588 (2) | 0.1526 (2) | 0.09472 (16) | 0.0188 (5) | |
C2* | 0.1903 (16) | 0.2047 (15) | 0.1340 (13) | 0.015 (4)* | 0.158 (7) |
H2* | 0.2296 | 0.2488 | 0.1769 | 0.018* | 0.158 (7) |
C3* | 0.0626 (15) | 0.2010 (15) | 0.1178 (13) | 0.018 (4)* | 0.158 (7) |
H3* | 0.0492 | 0.1846 | 0.1696 | 0.021* | 0.158 (7) |
C4* | 0.0047 (17) | 0.3077 (16) | 0.0896 (13) | 0.033 (6)* | 0.158 (7) |
H4*1 | −0.0765 | 0.3006 | 0.0805 | 0.05* | 0.158 (7) |
H4*2 | 0.019 | 0.3288 | 0.0401 | 0.05* | 0.158 (7) |
H4*3 | 0.0349 | 0.3614 | 0.1304 | 0.05* | 0.158 (7) |
C2 | 0.1867 (3) | 0.2313 (3) | 0.1022 (2) | 0.0165 (7) | 0.842 (7) |
H2 | 0.2191 | 0.2968 | 0.1236 | 0.02* | 0.842 (7) |
C3 | 0.0583 (3) | 0.2217 (2) | 0.0788 (2) | 0.0159 (8) | 0.842 (7) |
H3 | 0.0249 | 0.2644 | 0.0297 | 0.019* | 0.842 (7) |
C4 | 0.0130 (3) | 0.2648 (2) | 0.1460 (2) | 0.0207 (9) | 0.842 (7) |
H4A | −0.0692 | 0.2586 | 0.1297 | 0.031* | 0.842 (7) |
H4B | 0.0343 | 0.3391 | 0.156 | 0.031* | 0.842 (7) |
H4C | 0.0454 | 0.2238 | 0.1946 | 0.031* | 0.842 (7) |
C5 | 0.4129 (2) | 0.3340 (2) | 0.13473 (16) | 0.0193 (6) | |
C6 | 0.4104 (2) | 0.3935 (2) | 0.06523 (18) | 0.0275 (6) | |
H6 | 0.4175 | 0.3581 | 0.0196 | 0.033* | |
C7 | 0.3974 (3) | 0.5049 (3) | 0.0639 (2) | 0.0362 (8) | |
H7 | 0.3949 | 0.5434 | 0.0172 | 0.043* | |
C8 | 0.3881 (3) | 0.5588 (2) | 0.1317 (2) | 0.0334 (7) | |
H8 | 0.3789 | 0.6333 | 0.1305 | 0.04* | |
C9 | 0.3925 (3) | 0.5016 (2) | 0.20139 (19) | 0.0268 (6) | |
H9 | 0.3873 | 0.5376 | 0.2473 | 0.032* | |
C10 | 0.4047 (2) | 0.3900 (2) | 0.20241 (16) | 0.0207 (6) | |
H10 | 0.4074 | 0.3522 | 0.2493 | 0.025* | |
C11 | 0.4628 (2) | 0.1451 (2) | 0.23415 (16) | 0.0198 (6) | |
C12 | 0.5811 (2) | 0.1298 (2) | 0.26969 (17) | 0.0221 (6) | |
H12 | 0.6307 | 0.1414 | 0.2389 | 0.026* | |
C13 | 0.6257 (3) | 0.0976 (2) | 0.34997 (18) | 0.0280 (7) | |
H13 | 0.7046 | 0.0892 | 0.3728 | 0.034* | |
C14 | 0.5521 (3) | 0.0779 (2) | 0.39608 (18) | 0.0318 (7) | |
H14 | 0.5814 | 0.0554 | 0.4497 | 0.038* | |
C15 | 0.4345 (3) | 0.0920 (2) | 0.36160 (18) | 0.0299 (7) | |
H15 | 0.385 | 0.0787 | 0.3922 | 0.036* | |
C16 | 0.3904 (3) | 0.1260 (2) | 0.28159 (17) | 0.0250 (6) | |
H16 | 0.3117 | 0.1361 | 0.2594 | 0.03* | |
C17 | 0.2561 (2) | 0.1409 (2) | −0.06868 (16) | 0.0201 (6) | |
H17 | 0.2747 | 0.2091 | −0.0464 | 0.024* | |
C18 | 0.3328 (2) | 0.0533 (2) | −0.05998 (16) | 0.0211 (6) | |
H18 | 0.41 | 0.0528 | −0.0297 | 0.025* | |
C19 | 0.2703 (2) | −0.0333 (2) | −0.10591 (17) | 0.0230 (6) | |
H19 | 0.2998 | −0.1008 | −0.112 | 0.028* | |
C20 | 0.1572 (2) | −0.0003 (2) | −0.14037 (16) | 0.0209 (6) | |
H20 | 0.0982 | −0.0419 | −0.1735 | 0.025* | |
C21 | 0.1472 (2) | 0.1073 (2) | −0.11655 (15) | 0.0191 (6) | |
H21 | 0.0805 | 0.1485 | −0.1302 | 0.023* | |
C22 | 0.2717 (3) | −0.0906 (2) | 0.15281 (17) | 0.0264 (6) | |
H22 | 0.2647 | −0.0539 | 0.198 | 0.032* | |
C23 | 0.3658 (2) | −0.0839 (2) | 0.12128 (17) | 0.0232 (6) | |
H23 | 0.4307 | −0.0411 | 0.1413 | 0.028* | |
C24 | 0.3437 (2) | −0.1533 (2) | 0.05466 (17) | 0.0238 (6) | |
H24 | 0.3926 | −0.1664 | 0.0236 | 0.029* | |
C25 | 0.2353 (2) | −0.2000 (2) | 0.04250 (17) | 0.0224 (6) | |
H25 | 0.1988 | −0.2475 | 0.0012 | 0.027* | |
C26 | 0.1911 (3) | −0.1619 (2) | 0.10438 (17) | 0.0249 (6) | |
H26 | 0.1211 | −0.1809 | 0.1115 | 0.03* | |
Cl1 | 0.62697 (7) | 0.72608 (6) | 0.20773 (5) | 0.03334 (18) | |
Cl2 | 0.78777 (7) | 0.84031 (7) | 0.34367 (5) | 0.0421 (2) | |
C27 | 0.6760 (3) | 0.8527 (2) | 0.25177 (19) | 0.0323 (7) | |
H27A | 0.703 | 0.8948 | 0.2139 | 0.039* | |
H27B | 0.6124 | 0.8911 | 0.2616 | 0.039* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zr | 0.01496 (13) | 0.01013 (12) | 0.01270 (13) | 0.00006 (9) | 0.00542 (10) | 0.00019 (9) |
P | 0.0161 (3) | 0.0213 (4) | 0.0205 (4) | −0.0015 (3) | 0.0052 (3) | −0.0062 (3) |
S | 0.0175 (3) | 0.0146 (3) | 0.0254 (3) | −0.0039 (3) | 0.0109 (3) | −0.0078 (3) |
C1 | 0.0175 (13) | 0.0202 (13) | 0.0191 (14) | −0.0011 (11) | 0.0059 (11) | −0.0035 (11) |
C2 | 0.0196 (17) | 0.0132 (15) | 0.0174 (19) | −0.0042 (12) | 0.0066 (14) | −0.0010 (14) |
C3 | 0.0194 (17) | 0.0118 (15) | 0.0172 (19) | 0.0012 (12) | 0.0065 (14) | −0.0023 (13) |
C4 | 0.0222 (17) | 0.0169 (16) | 0.027 (2) | −0.0016 (13) | 0.0129 (14) | −0.0059 (13) |
C5 | 0.0123 (12) | 0.0236 (14) | 0.0209 (14) | −0.0025 (11) | 0.0034 (11) | 0.0000 (11) |
C6 | 0.0256 (15) | 0.0336 (16) | 0.0213 (15) | −0.0069 (13) | 0.0038 (12) | 0.0018 (12) |
C7 | 0.0332 (18) | 0.0381 (19) | 0.0336 (18) | −0.0073 (14) | 0.0043 (15) | 0.0138 (15) |
C8 | 0.0280 (16) | 0.0193 (15) | 0.048 (2) | −0.0027 (12) | 0.0039 (15) | 0.0057 (14) |
C9 | 0.0226 (15) | 0.0225 (14) | 0.0318 (17) | −0.0028 (12) | 0.0026 (13) | −0.0043 (12) |
C10 | 0.0211 (14) | 0.0189 (13) | 0.0194 (14) | −0.0031 (11) | 0.0020 (11) | 0.0013 (11) |
C11 | 0.0231 (14) | 0.0147 (12) | 0.0209 (14) | −0.0022 (11) | 0.0055 (11) | −0.0063 (10) |
C12 | 0.0214 (14) | 0.0179 (13) | 0.0264 (15) | −0.0012 (11) | 0.0065 (12) | −0.0047 (11) |
C13 | 0.0295 (16) | 0.0196 (14) | 0.0298 (17) | 0.0043 (12) | 0.0015 (13) | −0.0039 (12) |
C14 | 0.050 (2) | 0.0208 (14) | 0.0223 (15) | 0.0020 (14) | 0.0079 (15) | −0.0005 (12) |
C15 | 0.0411 (19) | 0.0256 (15) | 0.0293 (17) | −0.0036 (13) | 0.0200 (15) | −0.0035 (13) |
C16 | 0.0252 (15) | 0.0240 (14) | 0.0268 (15) | 0.0008 (12) | 0.0094 (13) | −0.0051 (12) |
C17 | 0.0271 (15) | 0.0174 (13) | 0.0162 (13) | −0.0048 (11) | 0.0071 (11) | 0.0035 (10) |
C18 | 0.0180 (13) | 0.0261 (14) | 0.0208 (14) | −0.0011 (11) | 0.0083 (11) | 0.0079 (12) |
C19 | 0.0301 (16) | 0.0213 (13) | 0.0235 (15) | 0.0051 (12) | 0.0172 (13) | 0.0029 (11) |
C20 | 0.0255 (14) | 0.0242 (14) | 0.0150 (13) | −0.0072 (12) | 0.0089 (11) | −0.0004 (11) |
C21 | 0.0194 (13) | 0.0229 (14) | 0.0157 (13) | 0.0025 (11) | 0.0062 (11) | 0.0062 (11) |
C22 | 0.0394 (18) | 0.0227 (14) | 0.0160 (14) | 0.0097 (13) | 0.0068 (13) | 0.0062 (11) |
C23 | 0.0243 (15) | 0.0162 (13) | 0.0248 (15) | 0.0026 (11) | 0.0009 (12) | 0.0045 (11) |
C24 | 0.0276 (15) | 0.0181 (13) | 0.0278 (16) | 0.0096 (12) | 0.0115 (13) | 0.0061 (11) |
C25 | 0.0310 (15) | 0.0096 (12) | 0.0249 (15) | 0.0020 (11) | 0.0058 (13) | 0.0012 (11) |
C26 | 0.0317 (16) | 0.0180 (14) | 0.0285 (16) | 0.0040 (12) | 0.0143 (13) | 0.0114 (12) |
Cl1 | 0.0319 (4) | 0.0308 (4) | 0.0352 (4) | −0.0045 (3) | 0.0068 (3) | 0.0023 (3) |
Cl2 | 0.0270 (4) | 0.0404 (5) | 0.0513 (5) | 0.0023 (3) | 0.0000 (4) | −0.0100 (4) |
C27 | 0.0430 (19) | 0.0248 (15) | 0.0312 (17) | −0.0053 (14) | 0.0141 (15) | 0.0047 (13) |
Geometric parameters (Å, º) top
Zr—Ct1 | 2.242 (3) | C7—H7 | 0.93 |
Zr—Ct2 | 2.242 (4) | C8—C9 | 1.386 (4) |
Zr—S | 2.6124 (7) | C8—H8 | 0.93 |
S—Zri | 2.7380 (7) | C9—C10 | 1.391 (4) |
Zr—C1 | 2.381 (3) | C9—H9 | 0.93 |
Zr—C17 | 2.541 (2) | C10—H10 | 0.93 |
Zr—C18 | 2.511 (2) | C11—C16 | 1.396 (4) |
Zr—C19 | 2.541 (3) | C11—C12 | 1.402 (4) |
Zr—C20 | 2.564 (3) | C12—C13 | 1.389 (4) |
Zr—C21 | 2.550 (2) | C12—H12 | 0.93 |
Zr—C22 | 2.550 (3) | C13—C14 | 1.391 (4) |
Zr—C23 | 2.557 (3) | C13—H13 | 0.93 |
Zr—C24 | 2.559 (3) | C14—C15 | 1.391 (4) |
Zr—C25 | 2.514 (3) | C14—H14 | 0.93 |
Zr—C26 | 2.525 (3) | C15—C16 | 1.391 (4) |
P—C1 | 1.856 (3) | C15—H15 | 0.93 |
P—C5 | 1.840 (3) | C16—H16 | 0.93 |
P—C11 | 1.850 (3) | C17—C21 | 1.401 (4) |
S—C3 | 1.811 (3) | C17—C18 | 1.413 (4) |
S—C3* | 1.815 (18) | C17—H17 | 0.93 |
C1—C2 | 1.347 (4) | C18—C19 | 1.416 (4) |
C1—C2* | 1.386 (18) | C18—H18 | 0.93 |
C2*—C3* | 1.50 (3) | C19—C20 | 1.391 (4) |
C2*—H2* | 0.93 | C19—H19 | 0.93 |
C3*—C4* | 1.51 (3) | C20—C21 | 1.413 (4) |
C3*—H3* | 0.98 | C20—H20 | 0.93 |
C4*—H4*1 | 0.96 | C21—H21 | 0.93 |
C4*—H4*2 | 0.96 | C22—C26 | 1.399 (4) |
C4*—H4*3 | 0.96 | C22—C23 | 1.415 (4) |
C2—C3 | 1.502 (4) | C22—H22 | 0.93 |
C2—H2 | 0.93 | C23—C24 | 1.398 (4) |
C3—C4 | 1.527 (4) | C23—H23 | 0.93 |
C3—H3 | 0.98 | C24—C25 | 1.402 (4) |
C4—H4A | 0.96 | C24—H24 | 0.93 |
C4—H4B | 0.96 | C25—C26 | 1.417 (4) |
C4—H4C | 0.96 | C25—H25 | 0.93 |
C5—C10 | 1.391 (4) | C26—H26 | 0.93 |
C5—C6 | 1.403 (4) | Cl1—C27 | 1.770 (3) |
C6—C7 | 1.391 (4) | Cl2—C27 | 1.763 (3) |
C6—H6 | 0.93 | C27—H27A | 0.97 |
C7—C8 | 1.385 (5) | C27—H27B | 0.97 |
| | | |
Ct1—Zr—Ct2 | 126.3 (1) | C2—C3—H3 | 108.6 |
Ct1—Zr—S | 113.22 (7) | C4—C3—H3 | 108.6 |
Ct1—Zr—Si | 103.22 (7) | S—C3—H3 | 108.6 |
Ct1—Zr—C1 | 102.88 (9) | C3—C4—H4A | 109.5 |
Ct2—Zr—S | 120.43 (7) | C3—C4—H4B | 109.5 |
Ct2—Zr—Si | 99.52 (7) | H4A—C4—H4B | 109.5 |
Ct2—Zr—C1 | 97.7 (1) | C3—C4—H4C | 109.5 |
S—Zr—Si | 61.07 (2) | H4A—C4—H4C | 109.5 |
C1—Zr—S | 70.33 (6) | H4B—C4—H4C | 109.5 |
C1—Zr—Si | 130.68 (7) | C10—C5—C6 | 118.0 (3) |
C3—S—Zr | 107.30 (10) | C10—C5—P | 124.6 (2) |
C3—S—Zri | 124.54 (10) | C6—C5—P | 117.1 (2) |
Zr—S—Zri | 118.93 (2) | C7—C6—C5 | 120.7 (3) |
C1—C2—C3 | 125.1 (3) | C7—C6—H6 | 119.6 |
C2—C3—C4 | 110.8 (3) | C5—C6—H6 | 119.6 |
C2—C3—S | 106.9 (2) | C8—C7—C6 | 120.3 (3) |
C4—C3—S | 113.2 (2) | C8—C7—H7 | 119.9 |
P—C1—Zr | 119.15 (12) | C6—C7—H7 | 119.9 |
C2—C1—P | 116.6 (2) | C7—C8—C9 | 119.8 (3) |
C2—C1—Zr | 122.3 (2) | C7—C8—H8 | 120.1 |
C1—Zr—C18 | 85.10 (9) | C9—C8—H8 | 120.1 |
C1—Zr—C25 | 131.27 (9) | C8—C9—C10 | 119.8 (3) |
C18—Zr—C25 | 104.18 (9) | C8—C9—H9 | 120.1 |
C1—Zr—C26 | 109.32 (9) | C10—C9—H9 | 120.1 |
C18—Zr—C26 | 132.07 (9) | C5—C10—C9 | 121.4 (3) |
C25—Zr—C26 | 32.66 (9) | C5—C10—H10 | 119.3 |
C1—Zr—C19 | 117.34 (9) | C9—C10—H10 | 119.3 |
C18—Zr—C19 | 32.56 (9) | C16—C11—C12 | 118.1 (3) |
C25—Zr—C19 | 85.24 (9) | C16—C11—P | 124.8 (2) |
C26—Zr—C19 | 117.90 (9) | C12—C11—P | 117.1 (2) |
C1—Zr—C17 | 69.84 (9) | C13—C12—C11 | 121.3 (3) |
C18—Zr—C17 | 32.47 (9) | C13—C12—H12 | 119.4 |
C25—Zr—C17 | 135.89 (9) | C11—C12—H12 | 119.4 |
C26—Zr—C17 | 163.54 (9) | C12—C13—C14 | 119.8 (3) |
C19—Zr—C17 | 53.24 (9) | C12—C13—H13 | 120.1 |
C1—Zr—C21 | 91.69 (9) | C14—C13—H13 | 120.1 |
C18—Zr—C21 | 53.60 (9) | C15—C14—C13 | 119.6 (3) |
C25—Zr—C21 | 132.56 (9) | C15—C14—H14 | 120.2 |
C26—Zr—C21 | 158.10 (9) | C13—C14—H14 | 120.2 |
C19—Zr—C21 | 53.08 (9) | C14—C15—C16 | 120.3 (3) |
C17—Zr—C21 | 31.95 (8) | C14—C15—H15 | 119.8 |
C1—Zr—C22 | 79.91 (9) | C16—C15—H15 | 119.8 |
C18—Zr—C22 | 118.65 (9) | C15—C16—C11 | 120.9 (3) |
C25—Zr—C22 | 53.35 (9) | C15—C16—H16 | 119.6 |
C26—Zr—C22 | 32.00 (9) | C11—C16—H16 | 119.6 |
C19—Zr—C22 | 125.52 (9) | C21—C17—C18 | 108.4 (2) |
C17—Zr—C22 | 137.55 (9) | C21—C17—Zr | 74.36 (14) |
C21—Zr—C22 | 169.41 (9) | C18—C17—Zr | 72.60 (14) |
C1—Zr—C23 | 80.36 (9) | C21—C17—H17 | 125.8 |
C18—Zr—C23 | 86.82 (9) | C18—C17—H17 | 125.8 |
C25—Zr—C23 | 53.25 (9) | Zr—C17—H17 | 119.1 |
C26—Zr—C23 | 53.32 (9) | C17—C18—C19 | 107.2 (2) |
C19—Zr—C23 | 96.38 (9) | C17—C18—Zr | 74.94 (14) |
C17—Zr—C23 | 111.32 (9) | C19—C18—Zr | 74.87 (15) |
C21—Zr—C23 | 140.27 (9) | C17—C18—H18 | 126.4 |
C22—Zr—C23 | 32.18 (9) | C19—C18—H18 | 126.4 |
C1—Zr—C24 | 110.05 (9) | Zr—C18—H18 | 116 |
C18—Zr—C24 | 78.85 (9) | C20—C19—C18 | 108.3 (2) |
C25—Zr—C24 | 32.06 (9) | C20—C19—Zr | 75.13 (15) |
C26—Zr—C24 | 53.23 (9) | C18—C19—Zr | 72.58 (15) |
C19—Zr—C24 | 73.16 (9) | C20—C19—H19 | 125.8 |
C17—Zr—C24 | 110.91 (9) | C18—C19—H19 | 125.8 |
C21—Zr—C24 | 125.94 (8) | Zr—C19—H19 | 118.3 |
C22—Zr—C24 | 52.79 (9) | C19—C20—C21 | 108.4 (2) |
C23—Zr—C24 | 31.72 (9) | C19—C20—Zr | 73.25 (15) |
C1—Zr—C20 | 121.54 (9) | C21—C20—Zr | 73.39 (14) |
C18—Zr—C20 | 53.26 (9) | C19—C20—H20 | 125.8 |
C25—Zr—C20 | 100.49 (9) | C21—C20—H20 | 125.8 |
C26—Zr—C20 | 128.79 (9) | Zr—C20—H20 | 119.4 |
C19—Zr—C20 | 31.62 (9) | C17—C21—C20 | 107.6 (2) |
C17—Zr—C20 | 52.83 (8) | C17—C21—Zr | 73.69 (14) |
C21—Zr—C20 | 32.09 (8) | C20—C21—Zr | 74.53 (15) |
C22—Zr—C20 | 152.29 (9) | C17—C21—H21 | 126.2 |
C23—Zr—C20 | 127.54 (9) | C20—C21—H21 | 126.2 |
C24—Zr—C20 | 100.63 (9) | Zr—C21—H21 | 117.6 |
C18—Zr—S | 138.03 (6) | C26—C22—C23 | 108.3 (2) |
C25—Zr—S | 117.66 (6) | C26—C22—Zr | 73.01 (15) |
C26—Zr—S | 88.90 (7) | C23—C22—Zr | 74.17 (15) |
C19—Zr—S | 143.37 (7) | C26—C22—H22 | 125.9 |
C17—Zr—S | 105.69 (6) | C23—C22—H22 | 125.9 |
C21—Zr—S | 92.60 (6) | Zr—C22—H22 | 118.8 |
C22—Zr—S | 90.63 (7) | C24—C23—C22 | 107.7 (3) |
C23—Zr—S | 120.15 (7) | C24—C23—Zr | 74.23 (16) |
C24—Zr—S | 140.94 (6) | C22—C23—Zr | 73.65 (16) |
C20—Zr—S | 112.25 (7) | C24—C23—H23 | 126.2 |
C5—P—C11 | 101.74 (12) | C22—C23—H23 | 126.2 |
C5—P—C1 | 102.48 (12) | Zr—C23—H23 | 118 |
C11—P—C1 | 103.05 (12) | C23—C24—C25 | 108.5 (2) |
C3—S—C3* | 22.5 (6) | C23—C24—Zr | 74.05 (15) |
C3*—S—Zr | 114.0 (6) | C25—C24—Zr | 72.19 (15) |
C3*—S—Zri | 126.4 (6) | C23—C24—H24 | 125.7 |
C2—C1—C2* | 26.6 (8) | C25—C24—H24 | 125.7 |
C2*—C1—P | 117.6 (8) | Zr—C24—H24 | 119.8 |
C2*—C1—Zr | 121.6 (8) | C24—C25—C26 | 107.8 (2) |
C1—C2*—C3* | 129.8 (16) | C24—C25—Zr | 75.75 (15) |
C1—C2*—H2* | 115.1 | C26—C25—Zr | 74.10 (15) |
C3*—C2*—H2* | 115.1 | C24—C25—H25 | 126.1 |
C2*—C3*—C4* | 113.1 (16) | C26—C25—H25 | 126.1 |
C2*—C3*—S | 101.9 (12) | Zr—C25—H25 | 116.2 |
C4*—C3*—S | 120.9 (15) | C22—C26—C25 | 107.7 (3) |
C2*—C3*—H3* | 106.6 | C22—C26—Zr | 75.00 (15) |
C4*—C3*—H3* | 106.6 | C25—C26—Zr | 73.24 (15) |
S—C3*—H3* | 106.6 | C22—C26—H26 | 126.2 |
C3*—C4*—H4*1 | 109.5 | C25—C26—H26 | 126.2 |
C3*—C4*—H4*2 | 109.5 | Zr—C26—H26 | 117.6 |
H4*1—C4*—H4*2 | 109.5 | Cl2—C27—Cl1 | 112.39 (17) |
C3*—C4*—H4*3 | 109.5 | Cl2—C27—H27A | 109.1 |
H4*1—C4*—H4*3 | 109.5 | Cl1—C27—H27A | 109.1 |
H4*2—C4*—H4*3 | 109.5 | Cl2—C27—H27B | 109.1 |
C1—C2—H2 | 117.4 | Cl1—C27—H27B | 109.1 |
C3—C2—H2 | 117.4 | H27A—C27—H27B | 107.9 |
Symmetry code: (i) −x, −y, −z. |