metal-organic compounds
{N,N′-Bis[2-(diphenylphosphanyl)ethan-1-ylidene]ethylenediamine}bromido(p-toluenesulfonylmethyl isocyanide)iron(II) tetraphenylborate
aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada
*Correspondence e-mail: rmorris@chem.utoronto.ca
In the title compound, [FeBr(C9H9NO2S)(C30H30N2P2)][B(C6H5)4], the FeII ion is in a distorted octahedral CBrN2P2 coordination geometry with a P—Fe—P angle of 109.95 (3)°. The relative orientation of the p-toluenesulfonylmethyl isocyanide ligand is defined by the C—S—C—N torsion angle of 67.1 (2)°. In the crystal, pairs of weak C—H⋯O hydrogen bonds connect the cations into inversion dimers, forming R22(8) rings.
CCDC reference: 990953
Related literature
For the synthesis, see: Mikhailine et al. (2008). For hydrogen-bond graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2012); cell SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 990953
10.1107/S1600536814005467/is5347sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814005467/is5347Isup2.hkl
The synthesis of the precursor [bis(acetonitrile)(N,N'-bis(2-(diphenylphosphanyl) ethyliedene)ethylenediamine) iron(II) tetraphenylborate] followed a previously published procedure (Mikhailine et al., 2008). Excess KBr (0.2 g, 1.68 mmol) was added to a solution of bis(acetonitrile)(N,N'-bis(2-(diphenylphosphanyl)ethyliedene)ethylenediamine) iron(II) tetraphenylborate (0.15 g, 0.119 mmol) in acetone (4 ml) in a three-necked round-bottom flask equipped with a magnetic stirring bar, a gas inlet, a reflux condenser and a rubber septum under an inert N2 atmosphere. para-Toluenesulfonylmethyl isocyanide (0.024 g, 0.119 mmol) in acetone (5 ml) was added with stirring at ambient temperatures. The flask was then placed into an oil bath and the reaction mixture heated to 313 K and stirred at this temperature for 30 min. The reaction mixture was allowed to cool to room temperature, hexanes (25 ml) was added, and the product isolated by filtration. The yellow precipitate was washed with water (2×10 ml), methanol (2×10 ml), and diethyl ether (2×10 ml)(Yield = 0.108 g, 80%). X-ray diffraction quality crystals were grown from the slow diffusion of diethyl ether into a dimethylsulfoxide solution of the title compound.
Hydrogen atoms were placed in calculated positions with C—H = 0.95–0.99 Å and included in the
in a riding-model approximation with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).Data collection: APEX2 (Bruker, 2012); cell
SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[FeBr(C9H9NO2S)(C30H30N2P2)](C24H20B) | Z = 2 |
Mr = 1130.70 | F(000) = 1172 |
Triclinic, P1 | Dx = 1.397 Mg m−3 |
a = 13.5738 (16) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 14.1207 (15) Å | Cell parameters from 9992 reflections |
c = 15.8419 (16) Å | θ = 3.6–65.8° |
α = 79.847 (4)° | µ = 4.42 mm−1 |
β = 76.873 (5)° | T = 147 K |
γ = 65.904 (5)° | Prism, yellow |
V = 2687.5 (5) Å3 | 0.05 × 0.03 × 0.02 mm |
Bruker Kappa APEX DUO CCD diffractometer | 7945 reflections with I > 2σ(I) |
Radiation source: Bruker ImuS with multi-layer optics | Rint = 0.057 |
ϕ and ω scans | θmax = 66.4°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −15→15 |
Tmin = 0.669, Tmax = 0.753 | k = −16→16 |
63879 measured reflections | l = −18→18 |
9108 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0408P)2 + 2.0605P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
9108 reflections | Δρmax = 0.48 e Å−3 |
668 parameters | Δρmin = −0.59 e Å−3 |
[FeBr(C9H9NO2S)(C30H30N2P2)](C24H20B) | γ = 65.904 (5)° |
Mr = 1130.70 | V = 2687.5 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.5738 (16) Å | Cu Kα radiation |
b = 14.1207 (15) Å | µ = 4.42 mm−1 |
c = 15.8419 (16) Å | T = 147 K |
α = 79.847 (4)° | 0.05 × 0.03 × 0.02 mm |
β = 76.873 (5)° |
Bruker Kappa APEX DUO CCD diffractometer | 9108 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | 7945 reflections with I > 2σ(I) |
Tmin = 0.669, Tmax = 0.753 | Rint = 0.057 |
63879 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.48 e Å−3 |
9108 reflections | Δρmin = −0.59 e Å−3 |
668 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Fe1 | 0.24184 (3) | 0.24713 (3) | 0.25224 (2) | 0.01682 (9) | |
Br1 | 0.33565 (2) | 0.07030 (2) | 0.20309 (2) | 0.02982 (8) | |
S1 | 0.13182 (5) | 0.54658 (5) | 0.45590 (4) | 0.02714 (14) | |
P1 | 0.10168 (5) | 0.25748 (4) | 0.19371 (4) | 0.01708 (13) | |
P2 | 0.34887 (5) | 0.31773 (4) | 0.15529 (4) | 0.01916 (13) | |
O1 | 0.07408 (17) | 0.64937 (16) | 0.48384 (13) | 0.0438 (5) | |
O2 | 0.12548 (16) | 0.45826 (16) | 0.51375 (12) | 0.0380 (5) | |
N1 | 0.16915 (17) | 0.18657 (15) | 0.35637 (13) | 0.0236 (4) | |
N2 | 0.35614 (17) | 0.20841 (15) | 0.32337 (13) | 0.0232 (4) | |
N3 | 0.12910 (16) | 0.45064 (15) | 0.32730 (13) | 0.0233 (4) | |
C1 | 0.0464 (2) | 0.17330 (19) | 0.27661 (16) | 0.0245 (5) | |
H1A | −0.0346 | 0.2058 | 0.2883 | 0.029* | |
H1B | 0.0685 | 0.1046 | 0.2550 | 0.029* | |
C2 | 0.0899 (2) | 0.15986 (19) | 0.35777 (16) | 0.0260 (5) | |
H2A | 0.0587 | 0.1314 | 0.4106 | 0.031* | |
C3 | 0.2166 (2) | 0.1740 (2) | 0.43463 (16) | 0.0314 (6) | |
H3A | 0.2019 | 0.1189 | 0.4773 | 0.038* | |
H3B | 0.1843 | 0.2400 | 0.4625 | 0.038* | |
C4 | 0.3391 (2) | 0.1438 (2) | 0.40458 (17) | 0.0327 (6) | |
H4A | 0.3717 | 0.1555 | 0.4497 | 0.039* | |
H4B | 0.3746 | 0.0691 | 0.3944 | 0.039* | |
C5 | 0.4415 (2) | 0.22964 (19) | 0.30114 (16) | 0.0253 (5) | |
H5A | 0.4926 | 0.2085 | 0.3397 | 0.030* | |
C6 | 0.4618 (2) | 0.2870 (2) | 0.21575 (16) | 0.0255 (5) | |
H6A | 0.5321 | 0.2441 | 0.1816 | 0.031* | |
H6B | 0.4672 | 0.3523 | 0.2245 | 0.031* | |
C7 | 0.17161 (18) | 0.37228 (18) | 0.29535 (14) | 0.0187 (5) | |
C8 | 0.0817 (2) | 0.54972 (18) | 0.35872 (15) | 0.0231 (5) | |
H8A | 0.0010 | 0.5721 | 0.3719 | 0.028* | |
H8B | 0.0997 | 0.6010 | 0.3134 | 0.028* | |
C11 | 0.2713 (2) | 0.5238 (2) | 0.42036 (16) | 0.0279 (6) | |
C12 | 0.3000 (3) | 0.6035 (2) | 0.37254 (19) | 0.0376 (7) | |
H12A | 0.2454 | 0.6678 | 0.3555 | 0.045* | |
C13 | 0.4097 (3) | 0.5877 (2) | 0.3500 (2) | 0.0424 (7) | |
H13A | 0.4301 | 0.6414 | 0.3161 | 0.051* | |
C14 | 0.4909 (2) | 0.4949 (2) | 0.37594 (18) | 0.0378 (7) | |
C15 | 0.4603 (2) | 0.4147 (2) | 0.42017 (19) | 0.0387 (7) | |
H15A | 0.5151 | 0.3495 | 0.4351 | 0.046* | |
C16 | 0.3508 (2) | 0.4283 (2) | 0.44297 (18) | 0.0330 (6) | |
H16A | 0.3305 | 0.3730 | 0.4736 | 0.040* | |
C17 | 0.6088 (3) | 0.4833 (3) | 0.3573 (2) | 0.0544 (9) | |
H17A | 0.6534 | 0.4164 | 0.3852 | 0.082* | |
H17B | 0.6151 | 0.5402 | 0.3803 | 0.082* | |
H17C | 0.6347 | 0.4856 | 0.2942 | 0.082* | |
C21 | −0.01598 (18) | 0.38122 (17) | 0.19108 (15) | 0.0190 (5) | |
C22 | −0.0468 (2) | 0.43710 (18) | 0.11316 (16) | 0.0228 (5) | |
H22A | −0.0102 | 0.4081 | 0.0595 | 0.027* | |
C23 | −0.1308 (2) | 0.5348 (2) | 0.11377 (17) | 0.0294 (6) | |
H23A | −0.1519 | 0.5721 | 0.0604 | 0.035* | |
C24 | −0.1840 (2) | 0.5786 (2) | 0.19106 (18) | 0.0321 (6) | |
H24A | −0.2400 | 0.6466 | 0.1907 | 0.039* | |
C25 | −0.1556 (2) | 0.5232 (2) | 0.26921 (17) | 0.0285 (6) | |
H25A | −0.1933 | 0.5525 | 0.3226 | 0.034* | |
C26 | −0.07257 (19) | 0.42549 (19) | 0.26938 (16) | 0.0229 (5) | |
H26A | −0.0535 | 0.3878 | 0.3231 | 0.028* | |
C31 | 0.2860 (2) | 0.46004 (18) | 0.13921 (15) | 0.0209 (5) | |
C32 | 0.3318 (2) | 0.5265 (2) | 0.15317 (18) | 0.0324 (6) | |
H32A | 0.4050 | 0.4991 | 0.1636 | 0.039* | |
C33 | 0.2701 (3) | 0.6336 (2) | 0.15184 (19) | 0.0390 (7) | |
H33A | 0.3015 | 0.6786 | 0.1622 | 0.047* | |
C34 | 0.1652 (3) | 0.6745 (2) | 0.13582 (18) | 0.0359 (7) | |
H34A | 0.1234 | 0.7472 | 0.1368 | 0.043* | |
C35 | 0.1197 (2) | 0.6100 (2) | 0.11815 (17) | 0.0322 (6) | |
H35A | 0.0477 | 0.6381 | 0.1050 | 0.039* | |
C36 | 0.1807 (2) | 0.50367 (19) | 0.12002 (16) | 0.0261 (5) | |
H36A | 0.1496 | 0.4594 | 0.1078 | 0.031* | |
C41 | 0.11374 (19) | 0.21067 (17) | 0.09031 (15) | 0.0199 (5) | |
C42 | 0.2042 (2) | 0.20105 (19) | 0.02548 (16) | 0.0252 (5) | |
H42A | 0.2626 | 0.2155 | 0.0360 | 0.030* | |
C43 | 0.2101 (2) | 0.1703 (2) | −0.05490 (17) | 0.0300 (6) | |
H43A | 0.2718 | 0.1649 | −0.0993 | 0.036* | |
C44 | 0.1263 (2) | 0.14770 (19) | −0.07000 (16) | 0.0285 (6) | |
H44A | 0.1301 | 0.1273 | −0.1251 | 0.034* | |
C45 | 0.0365 (2) | 0.15467 (19) | −0.00490 (17) | 0.0296 (6) | |
H45A | −0.0202 | 0.1372 | −0.0149 | 0.036* | |
C46 | 0.0293 (2) | 0.18725 (19) | 0.07497 (16) | 0.0247 (5) | |
H46A | −0.0330 | 0.1935 | 0.1190 | 0.030* | |
C51 | 0.42044 (19) | 0.2781 (2) | 0.04679 (16) | 0.0251 (5) | |
C52 | 0.4016 (2) | 0.3466 (2) | −0.02799 (17) | 0.0352 (6) | |
H52A | 0.3534 | 0.4173 | −0.0233 | 0.042* | |
C53 | 0.4532 (3) | 0.3119 (3) | −0.1095 (2) | 0.0487 (8) | |
H53A | 0.4401 | 0.3593 | −0.1602 | 0.058* | |
C54 | 0.5233 (3) | 0.2091 (3) | −0.1177 (2) | 0.0514 (9) | |
H54A | 0.5576 | 0.1858 | −0.1737 | 0.062* | |
C55 | 0.5430 (3) | 0.1412 (3) | −0.0444 (2) | 0.0477 (8) | |
H55A | 0.5916 | 0.0707 | −0.0499 | 0.057* | |
C56 | 0.4925 (2) | 0.1746 (2) | 0.0379 (2) | 0.0359 (6) | |
H56A | 0.5070 | 0.1268 | 0.0882 | 0.043* | |
C61 | 1.0789 (2) | 0.00682 (19) | −0.28860 (19) | 0.0302 (6) | |
C62 | 1.0266 (2) | 0.0422 (2) | −0.3622 (2) | 0.0421 (7) | |
H62A | 1.0705 | 0.0330 | −0.4185 | 0.051* | |
C63 | 0.9142 (3) | 0.0897 (2) | −0.3554 (3) | 0.0537 (9) | |
H63A | 0.8821 | 0.1126 | −0.4066 | 0.064* | |
C64 | 0.8484 (3) | 0.1038 (2) | −0.2751 (3) | 0.0548 (10) | |
H64A | 0.7711 | 0.1362 | −0.2707 | 0.066* | |
C65 | 0.8952 (3) | 0.0707 (2) | −0.2002 (3) | 0.0490 (9) | |
H65A | 0.8501 | 0.0802 | −0.1444 | 0.059* | |
C66 | 1.0101 (2) | 0.02279 (19) | −0.2078 (2) | 0.0358 (7) | |
H66A | 1.0416 | 0.0007 | −0.1564 | 0.043* | |
C71 | 1.2732 (2) | −0.09212 (18) | −0.39262 (16) | 0.0263 (6) | |
C72 | 1.2376 (2) | −0.1542 (2) | −0.42926 (18) | 0.0354 (6) | |
H72A | 1.1738 | −0.1659 | −0.3995 | 0.042* | |
C73 | 1.2918 (3) | −0.1992 (2) | −0.5074 (2) | 0.0424 (8) | |
H73A | 1.2655 | −0.2416 | −0.5286 | 0.051* | |
C74 | 1.3831 (3) | −0.1824 (2) | −0.55364 (19) | 0.0442 (8) | |
H74A | 1.4197 | −0.2122 | −0.6070 | 0.053* | |
C75 | 1.4201 (2) | −0.1216 (2) | −0.52095 (17) | 0.0359 (7) | |
H75A | 1.4829 | −0.1089 | −0.5519 | 0.043* | |
C76 | 1.3656 (2) | −0.07839 (19) | −0.44224 (16) | 0.0267 (6) | |
H76A | 1.3936 | −0.0370 | −0.4214 | 0.032* | |
C81 | 1.24591 (18) | −0.14122 (18) | −0.21894 (15) | 0.0205 (5) | |
C91 | 1.25498 (19) | 0.04773 (18) | −0.29289 (15) | 0.0203 (5) | |
C82 | 1.3511 (2) | 0.03139 (19) | −0.26384 (16) | 0.0234 (5) | |
H82A | 1.3896 | −0.0352 | −0.2365 | 0.028* | |
C92 | 1.25030 (19) | −0.12591 (19) | −0.13495 (16) | 0.0237 (5) | |
H92A | 1.2391 | −0.0580 | −0.1237 | 0.028* | |
C83 | 1.3928 (2) | 0.10846 (19) | −0.27321 (16) | 0.0266 (6) | |
H83A | 1.4579 | 0.0944 | −0.2519 | 0.032* | |
C93 | 1.2702 (2) | −0.2053 (2) | −0.06739 (17) | 0.0295 (6) | |
H93A | 1.2731 | −0.1911 | −0.0117 | 0.035* | |
C84 | 1.2859 (2) | −0.3048 (2) | −0.08126 (18) | 0.0326 (6) | |
H84A | 1.2992 | −0.3595 | −0.0355 | 0.039* | |
C94 | 1.3391 (2) | 0.2056 (2) | −0.31375 (17) | 0.0297 (6) | |
H94A | 1.3676 | 0.2584 | −0.3212 | 0.036* | |
C85 | 1.2820 (2) | −0.3233 (2) | −0.16267 (18) | 0.0329 (6) | |
H85A | 1.2925 | −0.3912 | −0.1730 | 0.039* | |
C95 | 1.2440 (2) | 0.22536 (19) | −0.34325 (17) | 0.0294 (6) | |
H95A | 1.2069 | 0.2918 | −0.3715 | 0.035* | |
C86 | 1.2629 (2) | −0.24353 (19) | −0.23000 (17) | 0.0258 (5) | |
H86A | 1.2613 | −0.2589 | −0.2856 | 0.031* | |
C96 | 1.2024 (2) | 0.14809 (18) | −0.33170 (16) | 0.0246 (5) | |
H96A | 1.1355 | 0.1640 | −0.3509 | 0.030* | |
B1 | 1.2134 (2) | −0.0454 (2) | −0.29695 (19) | 0.0231 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Fe1 | 0.01778 (19) | 0.01577 (18) | 0.01614 (19) | −0.00548 (14) | −0.00380 (15) | −0.00086 (14) |
Br1 | 0.03041 (15) | 0.02055 (13) | 0.03436 (16) | −0.00383 (11) | −0.00677 (11) | −0.00562 (11) |
S1 | 0.0310 (3) | 0.0315 (3) | 0.0180 (3) | −0.0101 (3) | −0.0016 (2) | −0.0079 (2) |
P1 | 0.0186 (3) | 0.0170 (3) | 0.0159 (3) | −0.0072 (2) | −0.0022 (2) | −0.0022 (2) |
P2 | 0.0173 (3) | 0.0211 (3) | 0.0187 (3) | −0.0069 (2) | −0.0024 (2) | −0.0029 (2) |
O1 | 0.0449 (12) | 0.0431 (12) | 0.0423 (12) | −0.0091 (9) | −0.0027 (9) | −0.0271 (10) |
O2 | 0.0371 (11) | 0.0532 (12) | 0.0217 (9) | −0.0197 (9) | −0.0052 (8) | 0.0078 (9) |
N1 | 0.0295 (11) | 0.0226 (10) | 0.0184 (10) | −0.0104 (9) | −0.0049 (9) | 0.0009 (8) |
N2 | 0.0251 (11) | 0.0204 (10) | 0.0224 (11) | −0.0057 (8) | −0.0076 (9) | −0.0011 (8) |
N3 | 0.0244 (11) | 0.0247 (11) | 0.0207 (10) | −0.0089 (9) | −0.0012 (9) | −0.0066 (9) |
C1 | 0.0287 (13) | 0.0243 (12) | 0.0244 (13) | −0.0158 (11) | −0.0039 (11) | 0.0007 (10) |
C2 | 0.0317 (14) | 0.0251 (13) | 0.0224 (13) | −0.0153 (11) | −0.0029 (11) | 0.0038 (10) |
C3 | 0.0398 (16) | 0.0411 (15) | 0.0176 (13) | −0.0207 (13) | −0.0102 (11) | 0.0068 (11) |
C4 | 0.0362 (15) | 0.0362 (15) | 0.0276 (14) | −0.0154 (12) | −0.0165 (12) | 0.0104 (12) |
C5 | 0.0221 (13) | 0.0254 (13) | 0.0286 (14) | −0.0053 (10) | −0.0112 (11) | −0.0032 (10) |
C6 | 0.0210 (12) | 0.0293 (13) | 0.0279 (14) | −0.0110 (10) | −0.0048 (10) | −0.0032 (11) |
C7 | 0.0163 (11) | 0.0256 (13) | 0.0154 (11) | −0.0104 (10) | −0.0039 (9) | 0.0022 (10) |
C8 | 0.0275 (13) | 0.0204 (12) | 0.0192 (12) | −0.0062 (10) | −0.0035 (10) | −0.0040 (10) |
C11 | 0.0328 (15) | 0.0324 (14) | 0.0219 (13) | −0.0144 (12) | −0.0036 (11) | −0.0081 (11) |
C12 | 0.0468 (18) | 0.0333 (15) | 0.0345 (16) | −0.0171 (13) | −0.0029 (13) | −0.0090 (12) |
C13 | 0.0517 (19) | 0.0412 (17) | 0.0417 (17) | −0.0286 (15) | 0.0049 (14) | −0.0125 (14) |
C14 | 0.0408 (17) | 0.0491 (18) | 0.0316 (15) | −0.0226 (14) | 0.0016 (13) | −0.0207 (13) |
C15 | 0.0368 (16) | 0.0406 (16) | 0.0397 (17) | −0.0110 (13) | −0.0113 (13) | −0.0095 (13) |
C16 | 0.0380 (16) | 0.0328 (14) | 0.0315 (15) | −0.0156 (12) | −0.0103 (12) | −0.0006 (12) |
C17 | 0.0423 (19) | 0.071 (2) | 0.060 (2) | −0.0307 (17) | 0.0093 (16) | −0.0335 (18) |
C21 | 0.0172 (11) | 0.0210 (12) | 0.0208 (12) | −0.0098 (9) | −0.0015 (9) | −0.0030 (9) |
C22 | 0.0244 (13) | 0.0235 (12) | 0.0203 (12) | −0.0100 (10) | −0.0027 (10) | −0.0012 (10) |
C23 | 0.0283 (14) | 0.0260 (13) | 0.0296 (14) | −0.0058 (11) | −0.0095 (11) | 0.0024 (11) |
C24 | 0.0235 (14) | 0.0257 (13) | 0.0405 (16) | −0.0022 (11) | −0.0047 (12) | −0.0058 (12) |
C25 | 0.0230 (13) | 0.0301 (13) | 0.0295 (14) | −0.0071 (11) | 0.0020 (11) | −0.0122 (11) |
C26 | 0.0212 (12) | 0.0260 (12) | 0.0217 (12) | −0.0087 (10) | −0.0040 (10) | −0.0030 (10) |
C31 | 0.0266 (13) | 0.0218 (12) | 0.0146 (11) | −0.0122 (10) | 0.0000 (10) | −0.0002 (9) |
C32 | 0.0395 (16) | 0.0316 (14) | 0.0332 (15) | −0.0187 (12) | −0.0150 (12) | 0.0027 (11) |
C33 | 0.065 (2) | 0.0277 (14) | 0.0367 (16) | −0.0268 (14) | −0.0196 (15) | 0.0028 (12) |
C34 | 0.0533 (19) | 0.0214 (13) | 0.0284 (14) | −0.0108 (12) | −0.0083 (13) | 0.0015 (11) |
C35 | 0.0331 (15) | 0.0266 (14) | 0.0310 (15) | −0.0095 (11) | −0.0055 (12) | 0.0071 (11) |
C36 | 0.0287 (14) | 0.0232 (12) | 0.0279 (14) | −0.0134 (11) | −0.0049 (11) | 0.0028 (10) |
C41 | 0.0251 (13) | 0.0154 (11) | 0.0185 (12) | −0.0064 (9) | −0.0047 (10) | −0.0021 (9) |
C42 | 0.0283 (14) | 0.0257 (13) | 0.0236 (13) | −0.0124 (11) | −0.0019 (11) | −0.0057 (10) |
C43 | 0.0342 (15) | 0.0302 (14) | 0.0210 (13) | −0.0098 (11) | 0.0018 (11) | −0.0054 (11) |
C44 | 0.0383 (15) | 0.0234 (13) | 0.0204 (13) | −0.0046 (11) | −0.0094 (11) | −0.0060 (10) |
C45 | 0.0341 (15) | 0.0263 (13) | 0.0315 (15) | −0.0094 (11) | −0.0131 (12) | −0.0065 (11) |
C46 | 0.0240 (13) | 0.0263 (13) | 0.0244 (13) | −0.0088 (10) | −0.0051 (10) | −0.0047 (10) |
C51 | 0.0179 (12) | 0.0358 (14) | 0.0254 (13) | −0.0140 (11) | 0.0012 (10) | −0.0090 (11) |
C52 | 0.0300 (15) | 0.0494 (17) | 0.0270 (14) | −0.0177 (13) | −0.0013 (12) | −0.0041 (13) |
C53 | 0.0466 (19) | 0.075 (2) | 0.0253 (15) | −0.0273 (18) | 0.0020 (14) | −0.0092 (15) |
C54 | 0.0410 (18) | 0.093 (3) | 0.0343 (18) | −0.0385 (19) | 0.0131 (14) | −0.0339 (18) |
C55 | 0.0361 (17) | 0.055 (2) | 0.057 (2) | −0.0209 (15) | 0.0097 (15) | −0.0333 (17) |
C56 | 0.0280 (14) | 0.0385 (15) | 0.0403 (16) | −0.0127 (12) | 0.0048 (12) | −0.0154 (13) |
C61 | 0.0250 (14) | 0.0177 (12) | 0.0492 (17) | −0.0106 (10) | −0.0093 (12) | 0.0035 (11) |
C62 | 0.0355 (17) | 0.0324 (15) | 0.059 (2) | −0.0135 (13) | −0.0213 (15) | 0.0132 (14) |
C63 | 0.0362 (18) | 0.0337 (17) | 0.090 (3) | −0.0112 (14) | −0.0290 (19) | 0.0151 (17) |
C64 | 0.0266 (16) | 0.0250 (15) | 0.111 (3) | −0.0026 (12) | −0.025 (2) | −0.0037 (17) |
C65 | 0.0334 (17) | 0.0264 (15) | 0.088 (3) | −0.0136 (13) | 0.0064 (17) | −0.0249 (16) |
C66 | 0.0235 (14) | 0.0204 (13) | 0.066 (2) | −0.0084 (11) | −0.0041 (13) | −0.0162 (13) |
C71 | 0.0342 (14) | 0.0211 (12) | 0.0240 (13) | −0.0086 (11) | −0.0135 (11) | 0.0031 (10) |
C72 | 0.0423 (17) | 0.0364 (15) | 0.0317 (15) | −0.0152 (13) | −0.0152 (13) | −0.0016 (12) |
C73 | 0.054 (2) | 0.0375 (16) | 0.0398 (17) | −0.0107 (14) | −0.0234 (15) | −0.0112 (13) |
C74 | 0.055 (2) | 0.0456 (18) | 0.0263 (15) | −0.0088 (15) | −0.0125 (14) | −0.0069 (13) |
C75 | 0.0448 (17) | 0.0318 (14) | 0.0227 (14) | −0.0081 (13) | −0.0048 (12) | 0.0004 (11) |
C76 | 0.0339 (14) | 0.0210 (12) | 0.0210 (13) | −0.0059 (11) | −0.0087 (11) | 0.0021 (10) |
C81 | 0.0132 (11) | 0.0214 (12) | 0.0238 (12) | −0.0054 (9) | 0.0009 (9) | −0.0032 (10) |
C91 | 0.0205 (12) | 0.0214 (12) | 0.0165 (12) | −0.0073 (10) | 0.0014 (9) | −0.0035 (9) |
C82 | 0.0237 (13) | 0.0215 (12) | 0.0215 (12) | −0.0061 (10) | −0.0017 (10) | −0.0027 (10) |
C92 | 0.0203 (12) | 0.0223 (12) | 0.0260 (13) | −0.0081 (10) | 0.0017 (10) | −0.0041 (10) |
C83 | 0.0232 (13) | 0.0297 (13) | 0.0270 (13) | −0.0105 (11) | 0.0006 (11) | −0.0087 (11) |
C93 | 0.0292 (14) | 0.0348 (14) | 0.0209 (13) | −0.0125 (11) | 0.0006 (11) | 0.0007 (11) |
C84 | 0.0335 (15) | 0.0282 (14) | 0.0288 (14) | −0.0115 (12) | −0.0002 (12) | 0.0076 (11) |
C94 | 0.0326 (15) | 0.0253 (13) | 0.0323 (14) | −0.0154 (11) | 0.0046 (12) | −0.0079 (11) |
C85 | 0.0345 (15) | 0.0222 (13) | 0.0386 (16) | −0.0120 (11) | 0.0015 (12) | −0.0023 (11) |
C95 | 0.0324 (15) | 0.0203 (12) | 0.0316 (14) | −0.0075 (11) | −0.0047 (12) | −0.0002 (11) |
C86 | 0.0252 (13) | 0.0239 (13) | 0.0268 (13) | −0.0099 (10) | −0.0001 (11) | −0.0033 (10) |
C96 | 0.0256 (13) | 0.0238 (12) | 0.0232 (13) | −0.0088 (10) | −0.0035 (10) | −0.0018 (10) |
B1 | 0.0215 (14) | 0.0222 (14) | 0.0260 (15) | −0.0080 (11) | −0.0061 (12) | −0.0013 (11) |
Fe1—C7 | 1.803 (2) | C36—H36A | 0.9500 |
Fe1—N2 | 1.965 (2) | C41—C42 | 1.386 (3) |
Fe1—N1 | 1.969 (2) | C41—C46 | 1.396 (3) |
Fe1—P1 | 2.2420 (7) | C42—C43 | 1.392 (3) |
Fe1—P2 | 2.2567 (7) | C42—H42A | 0.9500 |
Fe1—Br1 | 2.4700 (5) | C43—C44 | 1.378 (4) |
S1—O2 | 1.432 (2) | C43—H43A | 0.9500 |
S1—O1 | 1.434 (2) | C44—C45 | 1.388 (4) |
S1—C11 | 1.757 (3) | C44—H44A | 0.9500 |
S1—C8 | 1.806 (2) | C45—C46 | 1.391 (3) |
P1—C41 | 1.822 (2) | C45—H45A | 0.9500 |
P1—C21 | 1.825 (2) | C46—H46A | 0.9500 |
P1—C1 | 1.852 (2) | C51—C52 | 1.391 (4) |
P2—C51 | 1.830 (2) | C51—C56 | 1.398 (4) |
P2—C31 | 1.830 (2) | C52—C53 | 1.389 (4) |
P2—C6 | 1.853 (2) | C52—H52A | 0.9500 |
N1—C2 | 1.271 (3) | C53—C54 | 1.382 (5) |
N1—C3 | 1.475 (3) | C53—H53A | 0.9500 |
N2—C5 | 1.272 (3) | C54—C55 | 1.370 (5) |
N2—C4 | 1.471 (3) | C54—H54A | 0.9500 |
N3—C7 | 1.165 (3) | C55—C56 | 1.393 (4) |
N3—C8 | 1.409 (3) | C55—H55A | 0.9500 |
C1—C2 | 1.485 (3) | C56—H56A | 0.9500 |
C1—H1A | 0.9900 | C61—C66 | 1.396 (4) |
C1—H1B | 0.9900 | C61—C62 | 1.412 (4) |
C2—H2A | 0.9500 | C61—B1 | 1.649 (4) |
C3—C4 | 1.518 (4) | C62—C63 | 1.381 (4) |
C3—H3A | 0.9900 | C62—H62A | 0.9500 |
C3—H3B | 0.9900 | C63—C64 | 1.373 (5) |
C4—H4A | 0.9900 | C63—H63A | 0.9500 |
C4—H4B | 0.9900 | C64—C65 | 1.391 (5) |
C5—C6 | 1.479 (4) | C64—H64A | 0.9500 |
C5—H5A | 0.9500 | C65—C66 | 1.410 (4) |
C6—H6A | 0.9900 | C65—H65A | 0.9500 |
C6—H6B | 0.9900 | C66—H66A | 0.9500 |
C8—H8A | 0.9900 | C71—C76 | 1.387 (4) |
C8—H8B | 0.9900 | C71—C72 | 1.411 (4) |
C11—C12 | 1.384 (4) | C71—B1 | 1.657 (4) |
C11—C16 | 1.388 (4) | C72—C73 | 1.400 (4) |
C12—C13 | 1.381 (4) | C72—H72A | 0.9500 |
C12—H12A | 0.9500 | C73—C74 | 1.376 (5) |
C13—C14 | 1.392 (5) | C73—H73A | 0.9500 |
C13—H13A | 0.9500 | C74—C75 | 1.372 (4) |
C14—C15 | 1.385 (4) | C74—H74A | 0.9500 |
C14—C17 | 1.504 (4) | C75—C76 | 1.398 (4) |
C15—C16 | 1.387 (4) | C75—H75A | 0.9500 |
C15—H15A | 0.9500 | C76—H76A | 0.9500 |
C16—H16A | 0.9500 | C81—C92 | 1.403 (3) |
C17—H17A | 0.9800 | C81—C86 | 1.403 (3) |
C17—H17B | 0.9800 | C81—B1 | 1.650 (4) |
C17—H17C | 0.9800 | C91—C82 | 1.399 (3) |
C21—C22 | 1.394 (3) | C91—C96 | 1.401 (3) |
C21—C26 | 1.403 (3) | C91—B1 | 1.646 (4) |
C22—C23 | 1.385 (3) | C82—C83 | 1.391 (4) |
C22—H22A | 0.9500 | C82—H82A | 0.9500 |
C23—C24 | 1.380 (4) | C92—C93 | 1.391 (4) |
C23—H23A | 0.9500 | C92—H92A | 0.9500 |
C24—C25 | 1.387 (4) | C83—C94 | 1.382 (4) |
C24—H24A | 0.9500 | C83—H83A | 0.9500 |
C25—C26 | 1.380 (3) | C93—C84 | 1.384 (4) |
C25—H25A | 0.9500 | C93—H93A | 0.9500 |
C26—H26A | 0.9500 | C84—C85 | 1.376 (4) |
C31—C36 | 1.388 (4) | C84—H84A | 0.9500 |
C31—C32 | 1.388 (4) | C94—C95 | 1.377 (4) |
C32—C33 | 1.398 (4) | C94—H94A | 0.9500 |
C32—H32A | 0.9500 | C85—C86 | 1.391 (4) |
C33—C34 | 1.366 (4) | C85—H85A | 0.9500 |
C33—H33A | 0.9500 | C95—C96 | 1.389 (4) |
C34—C35 | 1.385 (4) | C95—H95A | 0.9500 |
C34—H34A | 0.9500 | C86—H86A | 0.9500 |
C35—C36 | 1.386 (4) | C96—H96A | 0.9500 |
C35—H35A | 0.9500 | ||
C7—Fe1—N2 | 90.99 (9) | C34—C33—H33A | 119.6 |
C7—Fe1—N1 | 88.74 (9) | C32—C33—H33A | 119.6 |
N2—Fe1—N1 | 82.96 (9) | C33—C34—C35 | 120.0 (2) |
C7—Fe1—P1 | 95.06 (7) | C33—C34—H34A | 120.0 |
N2—Fe1—P1 | 164.97 (6) | C35—C34—H34A | 120.0 |
N1—Fe1—P1 | 83.44 (6) | C34—C35—C36 | 119.0 (3) |
C7—Fe1—P2 | 87.36 (7) | C34—C35—H35A | 120.5 |
N2—Fe1—P2 | 84.02 (6) | C36—C35—H35A | 120.5 |
N1—Fe1—P2 | 166.33 (6) | C35—C36—C31 | 121.9 (2) |
P1—Fe1—P2 | 109.95 (3) | C35—C36—H36A | 119.0 |
C7—Fe1—Br1 | 176.19 (7) | C31—C36—H36A | 119.0 |
N2—Fe1—Br1 | 87.30 (6) | C42—C41—C46 | 119.4 (2) |
N1—Fe1—Br1 | 87.66 (6) | C42—C41—P1 | 120.88 (18) |
P1—Fe1—Br1 | 85.80 (2) | C46—C41—P1 | 119.65 (18) |
P2—Fe1—Br1 | 95.85 (2) | C41—C42—C43 | 120.4 (2) |
O2—S1—O1 | 119.89 (13) | C41—C42—H42A | 119.8 |
O2—S1—C11 | 107.42 (12) | C43—C42—H42A | 119.8 |
O1—S1—C11 | 109.80 (12) | C44—C43—C42 | 120.0 (2) |
O2—S1—C8 | 108.69 (12) | C44—C43—H43A | 120.0 |
O1—S1—C8 | 105.36 (12) | C42—C43—H43A | 120.0 |
C11—S1—C8 | 104.67 (12) | C43—C44—C45 | 120.1 (2) |
C41—P1—C21 | 102.28 (10) | C43—C44—H44A | 119.9 |
C41—P1—C1 | 104.54 (11) | C45—C44—H44A | 119.9 |
C21—P1—C1 | 102.80 (11) | C44—C45—C46 | 120.1 (2) |
C41—P1—Fe1 | 125.52 (8) | C44—C45—H45A | 119.9 |
C21—P1—Fe1 | 118.43 (8) | C46—C45—H45A | 119.9 |
C1—P1—Fe1 | 100.17 (8) | C45—C46—C41 | 119.9 (2) |
C51—P2—C31 | 104.38 (11) | C45—C46—H46A | 120.1 |
C51—P2—C6 | 103.41 (11) | C41—C46—H46A | 120.1 |
C31—P2—C6 | 105.94 (11) | C52—C51—C56 | 118.6 (2) |
C51—P2—Fe1 | 127.25 (8) | C52—C51—P2 | 122.0 (2) |
C31—P2—Fe1 | 113.16 (8) | C56—C51—P2 | 119.3 (2) |
C6—P2—Fe1 | 100.43 (8) | C53—C52—C51 | 120.2 (3) |
C2—N1—C3 | 122.3 (2) | C53—C52—H52A | 119.9 |
C2—N1—Fe1 | 124.73 (17) | C51—C52—H52A | 119.9 |
C3—N1—Fe1 | 112.98 (16) | C54—C53—C52 | 120.7 (3) |
C5—N2—C4 | 121.3 (2) | C54—C53—H53A | 119.6 |
C5—N2—Fe1 | 125.02 (17) | C52—C53—H53A | 119.6 |
C4—N2—Fe1 | 113.48 (16) | C55—C54—C53 | 119.5 (3) |
C7—N3—C8 | 174.7 (2) | C55—C54—H54A | 120.3 |
C2—C1—P1 | 108.78 (17) | C53—C54—H54A | 120.3 |
C2—C1—H1A | 109.9 | C54—C55—C56 | 120.7 (3) |
P1—C1—H1A | 109.9 | C54—C55—H55A | 119.7 |
C2—C1—H1B | 109.9 | C56—C55—H55A | 119.7 |
P1—C1—H1B | 109.9 | C55—C56—C51 | 120.2 (3) |
H1A—C1—H1B | 108.3 | C55—C56—H56A | 119.9 |
N1—C2—C1 | 119.9 (2) | C51—C56—H56A | 119.9 |
N1—C2—H2A | 120.1 | C66—C61—C62 | 116.1 (3) |
C1—C2—H2A | 120.1 | C66—C61—B1 | 121.5 (2) |
N1—C3—C4 | 106.7 (2) | C62—C61—B1 | 122.3 (3) |
N1—C3—H3A | 110.4 | C63—C62—C61 | 122.4 (3) |
C4—C3—H3A | 110.4 | C63—C62—H62A | 118.8 |
N1—C3—H3B | 110.4 | C61—C62—H62A | 118.8 |
C4—C3—H3B | 110.4 | C64—C63—C62 | 120.3 (3) |
H3A—C3—H3B | 108.6 | C64—C63—H63A | 119.8 |
N2—C4—C3 | 108.2 (2) | C62—C63—H63A | 119.8 |
N2—C4—H4A | 110.1 | C63—C64—C65 | 119.9 (3) |
C3—C4—H4A | 110.1 | C63—C64—H64A | 120.0 |
N2—C4—H4B | 110.1 | C65—C64—H64A | 120.0 |
C3—C4—H4B | 110.1 | C64—C65—C66 | 119.4 (3) |
H4A—C4—H4B | 108.4 | C64—C65—H65A | 120.3 |
N2—C5—C6 | 120.5 (2) | C66—C65—H65A | 120.3 |
N2—C5—H5A | 119.7 | C61—C66—C65 | 121.9 (3) |
C6—C5—H5A | 119.7 | C61—C66—H66A | 119.0 |
C5—C6—P2 | 109.99 (17) | C65—C66—H66A | 119.0 |
C5—C6—H6A | 109.7 | C76—C71—C72 | 113.6 (2) |
P2—C6—H6A | 109.7 | C76—C71—B1 | 123.6 (2) |
C5—C6—H6B | 109.7 | C72—C71—B1 | 122.7 (2) |
P2—C6—H6B | 109.7 | C73—C72—C71 | 123.0 (3) |
H6A—C6—H6B | 108.2 | C73—C72—H72A | 118.5 |
N3—C7—Fe1 | 176.1 (2) | C71—C72—H72A | 118.5 |
N3—C8—S1 | 110.59 (17) | C74—C73—C72 | 120.5 (3) |
N3—C8—H8A | 109.5 | C74—C73—H73A | 119.7 |
S1—C8—H8A | 109.5 | C72—C73—H73A | 119.7 |
N3—C8—H8B | 109.5 | C75—C74—C73 | 118.5 (3) |
S1—C8—H8B | 109.5 | C75—C74—H74A | 120.7 |
H8A—C8—H8B | 108.1 | C73—C74—H74A | 120.7 |
C12—C11—C16 | 121.0 (3) | C74—C75—C76 | 120.2 (3) |
C12—C11—S1 | 118.9 (2) | C74—C75—H75A | 119.9 |
C16—C11—S1 | 120.0 (2) | C76—C75—H75A | 119.9 |
C13—C12—C11 | 118.7 (3) | C71—C76—C75 | 124.2 (3) |
C13—C12—H12A | 120.7 | C71—C76—H76A | 117.9 |
C11—C12—H12A | 120.7 | C75—C76—H76A | 117.9 |
C12—C13—C14 | 121.6 (3) | C92—C81—C86 | 114.8 (2) |
C12—C13—H13A | 119.2 | C92—C81—B1 | 123.1 (2) |
C14—C13—H13A | 119.2 | C86—C81—B1 | 122.0 (2) |
C15—C14—C13 | 118.4 (3) | C82—C91—C96 | 115.2 (2) |
C15—C14—C17 | 121.1 (3) | C82—C91—B1 | 124.2 (2) |
C13—C14—C17 | 120.4 (3) | C96—C91—B1 | 119.9 (2) |
C14—C15—C16 | 121.0 (3) | C83—C82—C91 | 122.8 (2) |
C14—C15—H15A | 119.5 | C83—C82—H82A | 118.6 |
C16—C15—H15A | 119.5 | C91—C82—H82A | 118.6 |
C15—C16—C11 | 119.1 (3) | C93—C92—C81 | 123.2 (2) |
C15—C16—H16A | 120.4 | C93—C92—H92A | 118.4 |
C11—C16—H16A | 120.4 | C81—C92—H92A | 118.4 |
C14—C17—H17A | 109.5 | C94—C83—C82 | 119.7 (2) |
C14—C17—H17B | 109.5 | C94—C83—H83A | 120.2 |
H17A—C17—H17B | 109.5 | C82—C83—H83A | 120.2 |
C14—C17—H17C | 109.5 | C84—C93—C92 | 120.0 (2) |
H17A—C17—H17C | 109.5 | C84—C93—H93A | 120.0 |
H17B—C17—H17C | 109.5 | C92—C93—H93A | 120.0 |
C22—C21—C26 | 118.6 (2) | C85—C84—C93 | 118.7 (2) |
C22—C21—P1 | 122.08 (18) | C85—C84—H84A | 120.6 |
C26—C21—P1 | 119.14 (18) | C93—C84—H84A | 120.6 |
C23—C22—C21 | 120.2 (2) | C95—C94—C83 | 119.6 (2) |
C23—C22—H22A | 119.9 | C95—C94—H94A | 120.2 |
C21—C22—H22A | 119.9 | C83—C94—H94A | 120.2 |
C24—C23—C22 | 120.7 (2) | C84—C85—C86 | 120.8 (2) |
C24—C23—H23A | 119.7 | C84—C85—H85A | 119.6 |
C22—C23—H23A | 119.7 | C86—C85—H85A | 119.6 |
C23—C24—C25 | 119.8 (2) | C94—C95—C96 | 120.0 (2) |
C23—C24—H24A | 120.1 | C94—C95—H95A | 120.0 |
C25—C24—H24A | 120.1 | C96—C95—H95A | 120.0 |
C26—C25—C24 | 120.0 (2) | C85—C86—C81 | 122.5 (2) |
C26—C25—H25A | 120.0 | C85—C86—H86A | 118.8 |
C24—C25—H25A | 120.0 | C81—C86—H86A | 118.8 |
C25—C26—C21 | 120.7 (2) | C95—C96—C91 | 122.7 (2) |
C25—C26—H26A | 119.6 | C95—C96—H96A | 118.6 |
C21—C26—H26A | 119.6 | C91—C96—H96A | 118.6 |
C36—C31—C32 | 118.2 (2) | C91—B1—C61 | 107.87 (19) |
C36—C31—P2 | 117.03 (18) | C91—B1—C81 | 113.6 (2) |
C32—C31—P2 | 124.48 (19) | C61—B1—C81 | 108.6 (2) |
C31—C32—C33 | 119.9 (3) | C91—B1—C71 | 106.2 (2) |
C31—C32—H32A | 120.0 | C61—B1—C71 | 111.3 (2) |
C33—C32—H32A | 120.0 | C81—B1—C71 | 109.13 (19) |
C34—C33—C32 | 120.9 (3) | ||
C41—P1—C1—C2 | 148.07 (17) | C43—C44—C45—C46 | 1.8 (4) |
C21—P1—C1—C2 | −105.41 (18) | C44—C45—C46—C41 | −1.5 (4) |
Fe1—P1—C1—C2 | 17.05 (18) | C42—C41—C46—C45 | −0.1 (4) |
C3—N1—C2—C1 | −179.3 (2) | P1—C41—C46—C45 | 177.95 (19) |
Fe1—N1—C2—C1 | 0.3 (3) | C31—P2—C51—C52 | −13.4 (2) |
P1—C1—C2—N1 | −13.1 (3) | C6—P2—C51—C52 | −124.1 (2) |
C2—N1—C3—C4 | 143.4 (2) | Fe1—P2—C51—C52 | 121.4 (2) |
Fe1—N1—C3—C4 | −36.2 (2) | C31—P2—C51—C56 | 169.6 (2) |
C5—N2—C4—C3 | 153.1 (2) | C6—P2—C51—C56 | 59.0 (2) |
Fe1—N2—C4—C3 | −31.1 (3) | Fe1—P2—C51—C56 | −55.5 (2) |
N1—C3—C4—N2 | 42.2 (3) | C56—C51—C52—C53 | 0.5 (4) |
C4—N2—C5—C6 | 174.7 (2) | P2—C51—C52—C53 | −176.5 (2) |
Fe1—N2—C5—C6 | −0.5 (3) | C51—C52—C53—C54 | 0.3 (5) |
N2—C5—C6—P2 | 0.1 (3) | C52—C53—C54—C55 | −0.8 (5) |
C51—P2—C6—C5 | −132.30 (18) | C53—C54—C55—C56 | 0.5 (5) |
C31—P2—C6—C5 | 118.22 (17) | C54—C55—C56—C51 | 0.2 (4) |
Fe1—P2—C6—C5 | 0.29 (18) | C52—C51—C56—C55 | −0.7 (4) |
O2—S1—C8—N3 | −47.5 (2) | P2—C51—C56—C55 | 176.3 (2) |
O1—S1—C8—N3 | −177.15 (18) | C66—C61—C62—C63 | −0.2 (4) |
C11—S1—C8—N3 | 67.1 (2) | B1—C61—C62—C63 | −177.4 (3) |
O2—S1—C11—C12 | −171.6 (2) | C61—C62—C63—C64 | −0.2 (5) |
O1—S1—C11—C12 | −39.7 (2) | C62—C63—C64—C65 | 0.3 (5) |
C8—S1—C11—C12 | 72.9 (2) | C63—C64—C65—C66 | 0.0 (4) |
O2—S1—C11—C16 | 6.0 (2) | C62—C61—C66—C65 | 0.5 (4) |
O1—S1—C11—C16 | 137.9 (2) | B1—C61—C66—C65 | 177.8 (2) |
C8—S1—C11—C16 | −109.4 (2) | C64—C65—C66—C61 | −0.4 (4) |
C16—C11—C12—C13 | −2.2 (4) | C76—C71—C72—C73 | 1.2 (4) |
S1—C11—C12—C13 | 175.5 (2) | B1—C71—C72—C73 | −175.9 (2) |
C11—C12—C13—C14 | −1.5 (4) | C71—C72—C73—C74 | −1.4 (4) |
C12—C13—C14—C15 | 4.5 (4) | C72—C73—C74—C75 | 0.7 (4) |
C12—C13—C14—C17 | −174.6 (3) | C73—C74—C75—C76 | 0.1 (4) |
C13—C14—C15—C16 | −3.9 (4) | C72—C71—C76—C75 | −0.4 (4) |
C17—C14—C15—C16 | 175.2 (3) | B1—C71—C76—C75 | 176.7 (2) |
C14—C15—C16—C11 | 0.4 (4) | C74—C75—C76—C71 | −0.2 (4) |
C12—C11—C16—C15 | 2.7 (4) | C96—C91—C82—C83 | −0.6 (3) |
S1—C11—C16—C15 | −174.9 (2) | B1—C91—C82—C83 | 170.1 (2) |
C41—P1—C21—C22 | −24.7 (2) | C86—C81—C92—C93 | 0.2 (3) |
C1—P1—C21—C22 | −132.9 (2) | B1—C81—C92—C93 | 175.4 (2) |
Fe1—P1—C21—C22 | 117.89 (18) | C91—C82—C83—C94 | −0.9 (4) |
C41—P1—C21—C26 | 160.06 (19) | C81—C92—C93—C84 | −0.6 (4) |
C1—P1—C21—C26 | 51.8 (2) | C92—C93—C84—C85 | 0.4 (4) |
Fe1—P1—C21—C26 | −57.4 (2) | C82—C83—C94—C95 | 1.0 (4) |
C26—C21—C22—C23 | 0.8 (4) | C93—C84—C85—C86 | 0.2 (4) |
P1—C21—C22—C23 | −174.45 (19) | C83—C94—C95—C96 | 0.4 (4) |
C21—C22—C23—C24 | 0.7 (4) | C84—C85—C86—C81 | −0.5 (4) |
C22—C23—C24—C25 | −1.9 (4) | C92—C81—C86—C85 | 0.3 (4) |
C23—C24—C25—C26 | 1.5 (4) | B1—C81—C86—C85 | −174.9 (2) |
C24—C25—C26—C21 | 0.1 (4) | C94—C95—C96—C91 | −1.9 (4) |
C22—C21—C26—C25 | −1.3 (4) | C82—C91—C96—C95 | 1.9 (3) |
P1—C21—C26—C25 | 174.16 (19) | B1—C91—C96—C95 | −169.1 (2) |
C51—P2—C31—C36 | 90.5 (2) | C82—C91—B1—C61 | 153.5 (2) |
C6—P2—C31—C36 | −160.71 (19) | C96—C91—B1—C61 | −36.3 (3) |
Fe1—P2—C31—C36 | −51.6 (2) | C82—C91—B1—C81 | 33.0 (3) |
C51—P2—C31—C32 | −96.1 (2) | C96—C91—B1—C81 | −156.8 (2) |
C6—P2—C31—C32 | 12.7 (2) | C82—C91—B1—C71 | −87.0 (3) |
Fe1—P2—C31—C32 | 121.8 (2) | C96—C91—B1—C71 | 83.2 (3) |
C36—C31—C32—C33 | 3.1 (4) | C66—C61—B1—C91 | −83.2 (3) |
P2—C31—C32—C33 | −170.3 (2) | C62—C61—B1—C91 | 93.9 (3) |
C31—C32—C33—C34 | −0.9 (4) | C66—C61—B1—C81 | 40.4 (3) |
C32—C33—C34—C35 | −1.8 (4) | C62—C61—B1—C81 | −142.5 (2) |
C33—C34—C35—C36 | 2.2 (4) | C66—C61—B1—C71 | 160.6 (2) |
C34—C35—C36—C31 | 0.1 (4) | C62—C61—B1—C71 | −22.3 (3) |
C32—C31—C36—C35 | −2.7 (4) | C92—C81—B1—C91 | 33.7 (3) |
P2—C31—C36—C35 | 171.1 (2) | C86—C81—B1—C91 | −151.5 (2) |
C21—P1—C41—C42 | 114.2 (2) | C92—C81—B1—C61 | −86.4 (3) |
C1—P1—C41—C42 | −138.9 (2) | C86—C81—B1—C61 | 88.5 (3) |
Fe1—P1—C41—C42 | −24.7 (2) | C92—C81—B1—C71 | 152.1 (2) |
C21—P1—C41—C46 | −63.8 (2) | C86—C81—B1—C71 | −33.1 (3) |
C1—P1—C41—C46 | 43.1 (2) | C76—C71—B1—C91 | 19.4 (3) |
Fe1—P1—C41—C46 | 157.29 (15) | C72—C71—B1—C91 | −163.7 (2) |
C46—C41—C42—C43 | 1.3 (4) | C76—C71—B1—C61 | 136.6 (2) |
P1—C41—C42—C43 | −176.71 (19) | C72—C71—B1—C61 | −46.5 (3) |
C41—C42—C43—C44 | −1.0 (4) | C76—C71—B1—C81 | −103.5 (3) |
C42—C43—C44—C45 | −0.6 (4) | C72—C71—B1—C81 | 73.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.99 | 2.31 | 3.099 (3) | 136 |
Symmetry code: (i) −x, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O2i | 0.99 | 2.31 | 3.099 (3) | 136 |
Symmetry code: (i) −x, −y+1, −z+1. |
Acknowledgements
We thank NSERC Canada for a Discovery grant to RHM, and the Chemistry Department at the University of Toronto for funding this project through the Chemistry Teaching Fellowship Program.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Mikhailine, A. A., Kim, E., Dingels, C., Lough, A. J. & Morris, R. H. (2008). Inorg. Chem. 47, 6587–6589. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The cation of the title compound is shown in Fig. 1. The FeII ion is in a slightly-distorted octahedral coordination geometry with the P1—Fe1—P2 angle of 109.95 (3)° being the largest deviation from ideal octahedral geometry. The relative orientation of the para-toluenesulfonylmethylisocyanide ligand is defined by the C11—S1—C8—N3 torsion angle of 67.1 (2)°. In the crystal, a pair of weak C—H···O hydrogen bonds connect cations into an inversion dimer (Fig. 2) forming an R22(8) ring (Bernstein et al., 1995).