Experimental
Data collection
Oxford Diffraction KM4CCD diffractometer Absorption correction: none 15025 measured reflections 9143 independent reflections 8015 reflections with I > 2σ(I) Rint = 0.037
|
Refinement
R[F2 > 2σ(F2)] = 0.044 wR(F2) = 0.126 S = 1.19 9143 reflections 793 parameters 3 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 1.13 e Å−3 Δρmin = −0.66 e Å−3 Absolute structure: Flack (1983); 2104 Friedel pairs Flack parameter: 0.462 (16)
|
Zn1—N1 | 2.075 (5) | Zn1—S2 | 2.2664 (18) | Zn1—S1 | 2.2732 (16) | Zn1—O1 | 2.357 (4) | Zn1—O4 | 2.554 (4) | Zn2—N2 | 2.098 (5) | Zn2—O13 | 2.156 (5) | Zn2—S4 | 2.2627 (16) | Zn2—S3 | 2.2704 (17) | | N1—Zn1—S2 | 111.39 (14) | N1—Zn1—S1 | 107.81 (15) | S2—Zn1—S1 | 139.71 (7) | N1—Zn1—O1 | 92.46 (17) | S2—Zn1—O1 | 108.85 (12) | S1—Zn1—O1 | 77.94 (11) | N1—Zn1—O4 | 90.91 (17) | S2—Zn1—O4 | 74.68 (10) | S1—Zn1—O4 | 96.04 (11) | O1—Zn1—O4 | 173.77 (14) | N2—Zn2—O13 | 93.72 (19) | N2—Zn2—S4 | 105.61 (15) | O13—Zn2—S4 | 99.79 (13) | N2—Zn2—S3 | 109.24 (15) | O13—Zn2—S3 | 100.81 (13) | S4—Zn2—S3 | 137.87 (6) | | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | O13—H13A⋯O10 | 0.99 (1) | 1.86 (4) | 2.771 (6) | 151 (6) | | |
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
The title compound was obtained by the reaction of zinc acetyloacetonate (0.54 g, 2 mmol), 4,4'-bipyridine (0.312 g, 2 mmol) and tri-tert-butoxysilanethiol (0.9 ml, 3 mmol) in methanol (30 ml) and recrystallized from methanol at ambient temperature. For synthesis of substrates see, Becker et al. (2001).
The tBu group attached to O9 is disordered over two orientations with respect to rotation about O9—C33 bond. The site occupancies of the disordered atoms C34,C35,C36/C34A,C35A,C36A were refined to 0.52 (2)/0.48 (2). The same anisotropic displacement parameters were used for atoms C29, C30, C31 and C32, and for atoms C45, C46, C47 and C48. The hydroxyl H atom was located in a difference map and its positional parameters were refined with a O—H distance restraint of 0.99 (1) Å. The remaining H atoms were positioned geometrically and refined using a riding model, with C–H 0.95–0.98 Å and Uiso(H) = 1.2Ueq(C,O) or 1.5Ueq(methyl C). The highest residual electron-density peak is located 0.04 Å from atom C45.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
µ-4,4'-bipyridyl-1:2
κ2N:
N'-methanol-2
κO-tetrakis(tri-
tert-butoxysilanethiolato)-1
κ4O,S;2
κ2S-dizinc(II)
top Crystal data top [Zn2(C12H27O3SSi)4(C10H8N2)(CH4O)] | F(000) = 3088 |
Mr = 1436.91 | Dx = 1.202 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 12077 reflections |
a = 9.5897 (2) Å | θ = 2.2–32.5° |
b = 36.8378 (11) Å | µ = 0.82 mm−1 |
c = 22.7611 (5) Å | T = 120 K |
β = 99.127 (2)° | Prism, colourless |
V = 7938.9 (3) Å3 | 0.31 × 0.12 × 0.10 mm |
Z = 4 | |
Data collection top Oxford Diffraction KM-4-CCD diffractometer | 8015 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 8.1883 pixels mm-1 | θmax = 25.1°, θmin = 2.2° |
ω scans, 0.70 deg width | h = −7→11 |
15025 measured reflections | k = −33→43 |
9143 independent reflections | l = −27→27 |
Refinement top Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.071P)2 + 7.4679P] where P = (Fo2 + 2Fc2)/3 |
S = 1.19 | (Δ/σ)max = 0.013 |
9143 reflections | Δρmax = 1.13 e Å−3 |
793 parameters | Δρmin = −0.66 e Å−3 |
3 restraints | Absolute structure: Flack (1983); 2104 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.462 (16) |
Crystal data top [Zn2(C12H27O3SSi)4(C10H8N2)(CH4O)] | V = 7938.9 (3) Å3 |
Mr = 1436.91 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 9.5897 (2) Å | µ = 0.82 mm−1 |
b = 36.8378 (11) Å | T = 120 K |
c = 22.7611 (5) Å | 0.31 × 0.12 × 0.10 mm |
β = 99.127 (2)° | |
Data collection top Oxford Diffraction KM-4-CCD diffractometer | 8015 reflections with I > 2σ(I) |
15025 measured reflections | Rint = 0.037 |
9143 independent reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | Δρmax = 1.13 e Å−3 |
S = 1.19 | Δρmin = −0.66 e Å−3 |
9143 reflections | Absolute structure: Flack (1983); 2104 Friedel pairs |
793 parameters | Absolute structure parameter: 0.462 (16) |
3 restraints | |
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 | Occ. (<1) |
Zn1 | 0.87328 (8) | 0.419112 (17) | 0.52174 (3) | 0.02354 (17) | |
Zn2 | 0.02975 (8) | 0.208801 (17) | 0.49213 (3) | 0.02269 (17) | |
S1 | 0.75131 (17) | 0.47221 (4) | 0.50965 (7) | 0.0238 (3) | |
S2 | 1.08592 (17) | 0.39609 (4) | 0.50945 (7) | 0.0243 (3) | |
S3 | −0.13485 (16) | 0.22289 (4) | 0.54999 (7) | 0.0242 (3) | |
S4 | 0.12611 (17) | 0.15828 (4) | 0.45870 (7) | 0.0255 (3) | |
Si1 | 0.77984 (18) | 0.47450 (4) | 0.60187 (7) | 0.0198 (3) | |
Si2 | 1.02088 (18) | 0.39671 (4) | 0.41728 (7) | 0.0214 (4) | |
Si3 | −0.00917 (18) | 0.20566 (4) | 0.62862 (8) | 0.0222 (4) | |
Si4 | −0.04263 (19) | 0.14141 (4) | 0.39600 (8) | 0.0226 (4) | |
O1 | 0.8867 (5) | 0.43946 (11) | 0.62064 (18) | 0.0235 (9) | |
O2 | 0.6414 (5) | 0.46546 (11) | 0.6328 (2) | 0.0259 (10) | |
O3 | 0.8409 (5) | 0.51256 (11) | 0.63097 (18) | 0.0260 (10) | |
O4 | 0.8502 (4) | 0.40405 (11) | 0.41111 (18) | 0.0244 (9) | |
O5 | 1.1011 (5) | 0.42614 (11) | 0.38143 (19) | 0.0268 (10) | |
O6 | 1.0387 (5) | 0.35829 (11) | 0.3837 (2) | 0.0262 (10) | |
O7 | −0.0682 (5) | 0.17051 (12) | 0.6606 (2) | 0.0304 (10) | |
O8 | 0.0160 (5) | 0.23723 (12) | 0.6794 (2) | 0.0336 (11) | |
O9 | 0.1467 (5) | 0.19839 (12) | 0.6113 (2) | 0.0327 (11) | |
O10 | −0.0793 (5) | 0.17008 (11) | 0.3394 (2) | 0.0288 (10) | |
O11 | −0.0115 (5) | 0.10291 (10) | 0.36563 (19) | 0.0290 (10) | |
O12 | −0.1833 (5) | 0.14153 (12) | 0.42733 (19) | 0.0291 (10) | |
N1 | 0.7317 (5) | 0.37820 (12) | 0.5337 (2) | 0.0212 (11) | |
N2 | 0.1936 (6) | 0.24711 (13) | 0.5063 (2) | 0.0246 (12) | |
C1 | 0.9323 (8) | 0.42254 (17) | 0.6785 (3) | 0.0296 (15) | |
C2 | 0.9660 (11) | 0.4513 (2) | 0.7258 (4) | 0.052 (2) | |
H2A | 1.0365 | 0.4681 | 0.7144 | 0.078* | |
H2B | 1.0036 | 0.4398 | 0.7639 | 0.078* | |
H2C | 0.8798 | 0.4648 | 0.7299 | 0.078* | |
C3 | 1.0618 (8) | 0.4007 (2) | 0.6716 (4) | 0.0427 (19) | |
H3A | 1.0358 | 0.3814 | 0.6422 | 0.064* | |
H3B | 1.1015 | 0.3898 | 0.7099 | 0.064* | |
H3C | 1.1323 | 0.4166 | 0.658 | 0.064* | |
C4 | 0.8154 (9) | 0.39783 (19) | 0.6933 (3) | 0.0400 (17) | |
H4A | 0.732 | 0.4124 | 0.6974 | 0.06* | |
H4B | 0.8481 | 0.3851 | 0.7308 | 0.06* | |
H4C | 0.7908 | 0.3801 | 0.6613 | 0.06* | |
C5 | 0.5252 (8) | 0.48737 (18) | 0.6439 (3) | 0.0345 (16) | |
C6 | 0.5703 (10) | 0.5089 (2) | 0.7006 (4) | 0.048 (2) | |
H6A | 0.6128 | 0.4925 | 0.7324 | 0.072* | |
H6B | 0.4877 | 0.5208 | 0.7125 | 0.072* | |
H6C | 0.6396 | 0.5273 | 0.6937 | 0.072* | |
C7 | 0.4094 (9) | 0.4608 (2) | 0.6530 (5) | 0.053 (2) | |
H7A | 0.3749 | 0.4484 | 0.6154 | 0.08* | |
H7B | 0.3315 | 0.4739 | 0.6664 | 0.08* | |
H7C | 0.4473 | 0.4428 | 0.6831 | 0.08* | |
C8 | 0.4762 (8) | 0.5125 (2) | 0.5918 (4) | 0.0421 (18) | |
H8A | 0.5515 | 0.5298 | 0.5875 | 0.063* | |
H8B | 0.392 | 0.5257 | 0.5991 | 0.063* | |
H8C | 0.4536 | 0.4982 | 0.5553 | 0.063* | |
C9 | 0.9372 (7) | 0.53963 (17) | 0.6156 (3) | 0.0288 (15) | |
C10 | 0.9754 (12) | 0.5622 (2) | 0.6713 (4) | 0.058 (3) | |
H10A | 0.8898 | 0.5733 | 0.6818 | 0.086* | |
H10B | 1.0419 | 0.5813 | 0.6641 | 0.086* | |
H10C | 1.0192 | 0.5466 | 0.704 | 0.086* | |
C11 | 0.8618 (9) | 0.56240 (18) | 0.5651 (3) | 0.0369 (17) | |
H11A | 0.8297 | 0.5468 | 0.5308 | 0.055* | |
H11B | 0.9267 | 0.5808 | 0.5541 | 0.055* | |
H11C | 0.7803 | 0.5744 | 0.5778 | 0.055* | |
C12 | 1.0658 (9) | 0.5221 (2) | 0.5975 (5) | 0.062 (3) | |
H12A | 1.1144 | 0.5075 | 0.6306 | 0.092* | |
H12B | 1.1298 | 0.541 | 0.5871 | 0.092* | |
H12C | 1.0369 | 0.5064 | 0.5629 | 0.092* | |
C13 | 0.7380 (7) | 0.39982 (17) | 0.3603 (3) | 0.0274 (14) | |
C14 | 0.6177 (8) | 0.4239 (2) | 0.3728 (4) | 0.0407 (18) | |
H14A | 0.5851 | 0.4158 | 0.4093 | 0.061* | |
H14B | 0.5396 | 0.4225 | 0.3394 | 0.061* | |
H14C | 0.6507 | 0.4491 | 0.3777 | 0.061* | |
C15 | 0.6936 (8) | 0.35970 (18) | 0.3574 (3) | 0.0345 (16) | |
H15A | 0.7749 | 0.3445 | 0.3524 | 0.052* | |
H15B | 0.618 | 0.356 | 0.3236 | 0.052* | |
H15C | 0.6596 | 0.353 | 0.3943 | 0.052* | |
C16 | 0.7898 (8) | 0.4118 (2) | 0.3033 (3) | 0.0407 (18) | |
H16A | 0.8273 | 0.4366 | 0.3083 | 0.061* | |
H16B | 0.7109 | 0.4113 | 0.2702 | 0.061* | |
H16C | 0.8643 | 0.3954 | 0.2949 | 0.061* | |
C17 | 1.1433 (8) | 0.46377 (18) | 0.3905 (3) | 0.0329 (16) | |
C18 | 1.0280 (10) | 0.4857 (2) | 0.4107 (5) | 0.062 (3) | |
H18A | 0.9399 | 0.4822 | 0.3829 | 0.093* | |
H18B | 1.0538 | 0.5115 | 0.4117 | 0.093* | |
H18C | 1.0149 | 0.4779 | 0.4506 | 0.093* | |
C19 | 1.2794 (10) | 0.4656 (2) | 0.4338 (4) | 0.053 (2) | |
H19A | 1.2637 | 0.4565 | 0.4727 | 0.08* | |
H19B | 1.3119 | 0.4908 | 0.4377 | 0.08* | |
H19C | 1.3511 | 0.4507 | 0.4191 | 0.08* | |
C20 | 1.1674 (12) | 0.4766 (2) | 0.3301 (4) | 0.061 (3) | |
H20A | 1.2357 | 0.4606 | 0.3152 | 0.091* | |
H20B | 1.2043 | 0.5014 | 0.3331 | 0.091* | |
H20C | 1.0779 | 0.4761 | 0.3025 | 0.091* | |
C21 | 1.1553 (7) | 0.34331 (16) | 0.3591 (3) | 0.0277 (14) | |
C22 | 1.2936 (8) | 0.3511 (2) | 0.3992 (4) | 0.0384 (17) | |
H22A | 1.312 | 0.3772 | 0.3999 | 0.058* | |
H22B | 1.3703 | 0.3383 | 0.384 | 0.058* | |
H22C | 1.2881 | 0.3426 | 0.4396 | 0.058* | |
C23 | 1.1565 (9) | 0.3581 (2) | 0.2971 (3) | 0.0420 (18) | |
H23A | 1.071 | 0.3502 | 0.2708 | 0.063* | |
H23B | 1.24 | 0.349 | 0.2819 | 0.063* | |
H23C | 1.1594 | 0.3847 | 0.2985 | 0.063* | |
C24 | 1.1282 (9) | 0.30224 (18) | 0.3556 (4) | 0.0389 (17) | |
H24A | 1.1268 | 0.2927 | 0.3957 | 0.058* | |
H24B | 1.2034 | 0.2903 | 0.3383 | 0.058* | |
H24C | 1.0369 | 0.2975 | 0.3307 | 0.058* | |
C25 | −0.1345 (7) | 0.13685 (15) | 0.6370 (3) | 0.0261 (14) | |
C26 | −0.0969 (9) | 0.10901 (19) | 0.6873 (3) | 0.0394 (18) | |
H26A | 0.0055 | 0.1051 | 0.6944 | 0.059* | |
H26B | −0.145 | 0.086 | 0.6758 | 0.059* | |
H26C | −0.1272 | 0.1182 | 0.7237 | 0.059* | |
C27 | −0.2920 (8) | 0.14394 (19) | 0.6247 (3) | 0.0350 (16) | |
H27A | −0.3245 | 0.1516 | 0.6614 | 0.053* | |
H27B | −0.3415 | 0.1217 | 0.6099 | 0.053* | |
H27C | −0.3121 | 0.1631 | 0.5946 | 0.053* | |
C28 | −0.0792 (8) | 0.12438 (18) | 0.5822 (3) | 0.0333 (16) | |
H28A | −0.1017 | 0.1425 | 0.5506 | 0.05* | |
H28B | −0.1232 | 0.1012 | 0.5688 | 0.05* | |
H28C | 0.0235 | 0.1213 | 0.5913 | 0.05* | |
C29 | −0.0737 (11) | 0.2549 (3) | 0.7148 (5) | 0.0671 (14) | |
C30 | −0.2263 (10) | 0.2463 (3) | 0.6977 (5) | 0.0671 (14) | |
H30A | −0.2587 | 0.2547 | 0.6569 | 0.101* | |
H30B | −0.2803 | 0.2587 | 0.7249 | 0.101* | |
H30C | −0.2404 | 0.2201 | 0.6999 | 0.101* | |
C31 | −0.0402 (11) | 0.2948 (3) | 0.7126 (5) | 0.0671 (14) | |
H31A | 0.0621 | 0.2984 | 0.7227 | 0.101* | |
H31B | −0.0878 | 0.3079 | 0.7413 | 0.101* | |
H31C | −0.0731 | 0.3042 | 0.6725 | 0.101* | |
C32 | −0.0275 (11) | 0.2409 (3) | 0.7777 (5) | 0.0671 (14) | |
H32A | −0.0693 | 0.217 | 0.7818 | 0.101* | |
H32B | −0.0593 | 0.2578 | 0.8061 | 0.101* | |
H32C | 0.0757 | 0.239 | 0.7856 | 0.101* | |
C33 | 0.2783 (7) | 0.1869 (2) | 0.6471 (4) | 0.0407 (18) | |
C34 | 0.399 (3) | 0.2111 (7) | 0.6362 (11) | 0.046 (5) | 0.52 (2) |
H34A | 0.4824 | 0.206 | 0.6661 | 0.07* | 0.52 (2) |
H34B | 0.3719 | 0.2366 | 0.6391 | 0.07* | 0.52 (2) |
H34C | 0.4218 | 0.2064 | 0.5964 | 0.07* | 0.52 (2) |
C35 | 0.3074 (16) | 0.1498 (4) | 0.6381 (8) | 0.036 (4) | 0.52 (2) |
H35A | 0.3988 | 0.1434 | 0.6615 | 0.054* | 0.52 (2) |
H35B | 0.3104 | 0.1456 | 0.5958 | 0.054* | 0.52 (2) |
H35C | 0.2332 | 0.1348 | 0.6507 | 0.054* | 0.52 (2) |
C36 | 0.2727 (17) | 0.1917 (5) | 0.7189 (7) | 0.044 (5) | 0.52 (2) |
H36A | 0.27 | 0.2175 | 0.7287 | 0.066* | 0.52 (2) |
H36B | 0.3568 | 0.1806 | 0.7421 | 0.066* | 0.52 (2) |
H36C | 0.1879 | 0.1797 | 0.7286 | 0.066* | 0.52 (2) |
C34A | 0.365 (3) | 0.2192 (6) | 0.6588 (12) | 0.045 (6) | 0.48 (2) |
H34D | 0.4557 | 0.2127 | 0.6825 | 0.067* | 0.48 (2) |
H34E | 0.3162 | 0.2368 | 0.6808 | 0.067* | 0.48 (2) |
H34F | 0.3805 | 0.2299 | 0.621 | 0.067* | 0.48 (2) |
C35A | 0.3435 (18) | 0.1624 (5) | 0.5985 (9) | 0.044 (6) | 0.48 (2) |
H35D | 0.4311 | 0.1508 | 0.6177 | 0.065* | 0.48 (2) |
H35E | 0.3636 | 0.178 | 0.5659 | 0.065* | 0.48 (2) |
H35F | 0.2751 | 0.1437 | 0.5827 | 0.065* | 0.48 (2) |
C36A | 0.2532 (19) | 0.1649 (6) | 0.6954 (10) | 0.058 (7) | 0.48 (2) |
H36D | 0.1923 | 0.178 | 0.719 | 0.088* | 0.48 (2) |
H36E | 0.3433 | 0.1592 | 0.7206 | 0.088* | 0.48 (2) |
H36F | 0.2067 | 0.1423 | 0.6802 | 0.088* | 0.48 (2) |
C37 | −0.0162 (8) | 0.17337 (18) | 0.2852 (3) | 0.0321 (16) | |
C38 | −0.0609 (9) | 0.20988 (19) | 0.2604 (4) | 0.0411 (18) | |
H38A | −0.1642 | 0.2111 | 0.2521 | 0.062* | |
H38B | −0.0226 | 0.2138 | 0.2234 | 0.062* | |
H38C | −0.025 | 0.2287 | 0.2893 | 0.062* | |
C39 | 0.1417 (9) | 0.1706 (2) | 0.2994 (4) | 0.0427 (19) | |
H39A | 0.1778 | 0.1894 | 0.3283 | 0.064* | |
H39B | 0.1823 | 0.174 | 0.2629 | 0.064* | |
H39C | 0.168 | 0.1466 | 0.3161 | 0.064* | |
C40 | −0.0791 (11) | 0.1440 (2) | 0.2413 (3) | 0.051 (2) | |
H40A | −0.0577 | 0.12 | 0.2591 | 0.077* | |
H40B | −0.0383 | 0.1461 | 0.2046 | 0.077* | |
H40C | −0.1817 | 0.1472 | 0.2322 | 0.077* | |
C41 | 0.0531 (8) | 0.06921 (17) | 0.3891 (3) | 0.0327 (16) | |
C42 | 0.2117 (9) | 0.0722 (2) | 0.3932 (4) | 0.046 (2) | |
H42A | 0.235 | 0.0791 | 0.3543 | 0.069* | |
H42B | 0.2554 | 0.0488 | 0.4054 | 0.069* | |
H42C | 0.2475 | 0.0908 | 0.4227 | 0.069* | |
C43 | −0.0073 (12) | 0.04046 (19) | 0.3439 (4) | 0.058 (2) | |
H43A | −0.1103 | 0.0397 | 0.3413 | 0.087* | |
H43B | 0.0325 | 0.0167 | 0.3566 | 0.087* | |
H43C | 0.0169 | 0.0465 | 0.3048 | 0.087* | |
C44 | 0.0133 (9) | 0.06086 (18) | 0.4498 (3) | 0.0386 (18) | |
H44A | 0.051 | 0.0798 | 0.4781 | 0.058* | |
H44B | 0.053 | 0.0373 | 0.4638 | 0.058* | |
H44C | −0.0898 | 0.0601 | 0.4466 | 0.058* | |
C45 | −0.3318 (11) | 0.1365 (3) | 0.4069 (5) | 0.0726 (15) | |
C46 | −0.3974 (10) | 0.1729 (3) | 0.4057 (5) | 0.0726 (15) | |
H46A | −0.3683 | 0.185 | 0.4441 | 0.109* | |
H46B | −0.5005 | 0.1705 | 0.3982 | 0.109* | |
H46C | −0.3669 | 0.1875 | 0.374 | 0.109* | |
C47 | −0.3877 (10) | 0.1155 (3) | 0.4557 (5) | 0.0726 (15) | |
H47A | −0.3379 | 0.0923 | 0.4621 | 0.109* | |
H47B | −0.489 | 0.111 | 0.4438 | 0.109* | |
H47C | −0.3724 | 0.1297 | 0.4926 | 0.109* | |
C48 | −0.3621 (10) | 0.1192 (3) | 0.3481 (5) | 0.0726 (15) | |
H48A | −0.3231 | 0.1341 | 0.3189 | 0.109* | |
H48B | −0.4645 | 0.117 | 0.3362 | 0.109* | |
H48C | −0.3189 | 0.0951 | 0.3499 | 0.109* | |
C49 | 0.7655 (7) | 0.34292 (15) | 0.5319 (3) | 0.0252 (14) | |
H49 | 0.8607 | 0.3366 | 0.53 | 0.03* | |
C50 | 0.6686 (7) | 0.31558 (16) | 0.5325 (3) | 0.0256 (14) | |
H50 | 0.6969 | 0.2909 | 0.5313 | 0.031* | |
C51 | 0.5279 (7) | 0.32437 (15) | 0.5350 (3) | 0.0232 (13) | |
C52 | 0.4154 (7) | 0.29640 (16) | 0.5279 (3) | 0.0251 (14) | |
C53 | 0.4244 (7) | 0.26550 (17) | 0.4945 (3) | 0.0294 (15) | |
H53 | 0.5077 | 0.2607 | 0.4782 | 0.035* | |
C54 | 0.3124 (7) | 0.24173 (17) | 0.4849 (3) | 0.0272 (15) | |
H54 | 0.3208 | 0.2205 | 0.4619 | 0.033* | |
C56 | 0.1850 (7) | 0.27639 (16) | 0.5404 (3) | 0.0272 (14) | |
H56 | 0.1014 | 0.28 | 0.5572 | 0.033* | |
C57 | 0.2920 (7) | 0.30154 (16) | 0.5523 (3) | 0.0286 (15) | |
H57 | 0.2821 | 0.3221 | 0.5765 | 0.034* | |
C58 | 0.4954 (7) | 0.36096 (15) | 0.5397 (3) | 0.0222 (13) | |
H58 | 0.4023 | 0.3681 | 0.5438 | 0.027* | |
C59 | 0.5983 (7) | 0.38676 (16) | 0.5385 (3) | 0.0265 (14) | |
H59 | 0.5739 | 0.4116 | 0.541 | 0.032* | |
C60 | −0.1725 (9) | 0.2591 (2) | 0.4021 (4) | 0.0415 (18) | |
H60A | −0.2562 | 0.2493 | 0.4163 | 0.062* | |
H60B | −0.1969 | 0.2658 | 0.3601 | 0.062* | |
H60C | −0.1388 | 0.2806 | 0.4255 | 0.062* | |
O13 | −0.0646 (5) | 0.23231 (11) | 0.4085 (2) | 0.0299 (10) | |
H13A | −0.076 (8) | 0.2162 (16) | 0.3734 (19) | 0.036* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0201 (4) | 0.0164 (3) | 0.0347 (4) | −0.0013 (3) | 0.0061 (3) | 0.0003 (3) |
Zn2 | 0.0219 (4) | 0.0166 (3) | 0.0305 (4) | −0.0032 (3) | 0.0070 (3) | −0.0025 (3) |
S1 | 0.0293 (8) | 0.0179 (7) | 0.0232 (8) | 0.0019 (6) | 0.0014 (7) | 0.0007 (6) |
S2 | 0.0197 (7) | 0.0307 (8) | 0.0220 (8) | 0.0022 (7) | 0.0015 (6) | −0.0003 (6) |
S3 | 0.0215 (8) | 0.0227 (7) | 0.0289 (8) | 0.0030 (6) | 0.0053 (6) | 0.0010 (6) |
S4 | 0.0224 (8) | 0.0201 (7) | 0.0344 (9) | −0.0028 (6) | 0.0052 (7) | −0.0070 (6) |
Si1 | 0.0220 (8) | 0.0161 (7) | 0.0213 (8) | −0.0018 (7) | 0.0037 (7) | 0.0007 (6) |
Si2 | 0.0199 (8) | 0.0228 (8) | 0.0213 (9) | −0.0025 (7) | 0.0024 (7) | 0.0000 (6) |
Si3 | 0.0190 (8) | 0.0197 (8) | 0.0286 (9) | 0.0022 (7) | 0.0057 (7) | −0.0007 (7) |
Si4 | 0.0254 (9) | 0.0191 (8) | 0.0242 (9) | −0.0060 (7) | 0.0068 (7) | −0.0028 (7) |
O1 | 0.025 (2) | 0.023 (2) | 0.020 (2) | −0.0015 (18) | −0.0018 (18) | 0.0022 (17) |
O2 | 0.028 (2) | 0.018 (2) | 0.032 (2) | −0.0014 (18) | 0.008 (2) | 0.0051 (17) |
O3 | 0.032 (3) | 0.021 (2) | 0.026 (2) | −0.0078 (19) | 0.007 (2) | −0.0009 (17) |
O4 | 0.021 (2) | 0.030 (2) | 0.022 (2) | 0.0007 (19) | 0.0027 (18) | −0.0019 (18) |
O5 | 0.031 (2) | 0.024 (2) | 0.025 (2) | −0.0058 (19) | 0.003 (2) | 0.0005 (18) |
O6 | 0.023 (2) | 0.025 (2) | 0.031 (2) | −0.0030 (19) | 0.0070 (19) | −0.0006 (18) |
O7 | 0.034 (3) | 0.029 (2) | 0.029 (2) | −0.004 (2) | 0.006 (2) | 0.0001 (19) |
O8 | 0.026 (2) | 0.036 (3) | 0.038 (3) | 0.000 (2) | 0.005 (2) | −0.010 (2) |
O9 | 0.024 (2) | 0.037 (3) | 0.039 (3) | 0.007 (2) | 0.009 (2) | 0.008 (2) |
O10 | 0.034 (3) | 0.022 (2) | 0.031 (2) | −0.004 (2) | 0.007 (2) | −0.0002 (18) |
O11 | 0.042 (3) | 0.021 (2) | 0.024 (2) | −0.005 (2) | 0.004 (2) | −0.0030 (17) |
O12 | 0.027 (2) | 0.035 (2) | 0.027 (2) | −0.009 (2) | 0.008 (2) | −0.0058 (19) |
N1 | 0.019 (3) | 0.017 (2) | 0.027 (3) | −0.001 (2) | 0.004 (2) | −0.004 (2) |
N2 | 0.025 (3) | 0.021 (3) | 0.028 (3) | −0.006 (2) | 0.005 (2) | 0.003 (2) |
C1 | 0.033 (4) | 0.032 (3) | 0.022 (3) | 0.000 (3) | 0.000 (3) | 0.005 (3) |
C2 | 0.078 (6) | 0.039 (4) | 0.032 (4) | −0.003 (4) | −0.013 (4) | 0.004 (3) |
C3 | 0.039 (4) | 0.049 (4) | 0.041 (4) | 0.017 (4) | 0.006 (4) | 0.022 (3) |
C4 | 0.047 (5) | 0.037 (4) | 0.037 (4) | −0.002 (4) | 0.008 (4) | 0.013 (3) |
C5 | 0.032 (4) | 0.028 (3) | 0.048 (4) | 0.003 (3) | 0.020 (3) | 0.010 (3) |
C6 | 0.070 (6) | 0.037 (4) | 0.045 (5) | 0.007 (4) | 0.031 (4) | 0.004 (3) |
C7 | 0.031 (4) | 0.049 (5) | 0.085 (7) | 0.000 (4) | 0.025 (4) | 0.024 (4) |
C8 | 0.029 (4) | 0.040 (4) | 0.059 (5) | 0.009 (3) | 0.012 (4) | 0.010 (4) |
C9 | 0.033 (4) | 0.024 (3) | 0.028 (4) | −0.011 (3) | 0.000 (3) | 0.003 (3) |
C10 | 0.088 (7) | 0.048 (5) | 0.034 (4) | −0.043 (5) | 0.003 (4) | −0.003 (4) |
C11 | 0.043 (4) | 0.026 (4) | 0.041 (4) | −0.005 (3) | 0.003 (3) | 0.002 (3) |
C12 | 0.029 (4) | 0.047 (5) | 0.109 (8) | −0.009 (4) | 0.013 (5) | 0.020 (5) |
C13 | 0.023 (3) | 0.028 (3) | 0.028 (4) | −0.002 (3) | −0.005 (3) | −0.003 (3) |
C14 | 0.023 (4) | 0.054 (5) | 0.042 (4) | 0.010 (3) | −0.004 (3) | −0.011 (4) |
C15 | 0.034 (4) | 0.042 (4) | 0.026 (4) | −0.007 (3) | 0.000 (3) | −0.007 (3) |
C16 | 0.036 (4) | 0.058 (5) | 0.027 (4) | −0.010 (4) | −0.001 (3) | 0.002 (3) |
C17 | 0.034 (4) | 0.028 (3) | 0.036 (4) | −0.011 (3) | 0.007 (3) | 0.002 (3) |
C18 | 0.057 (6) | 0.023 (4) | 0.110 (8) | −0.007 (4) | 0.024 (6) | −0.003 (4) |
C19 | 0.053 (5) | 0.052 (5) | 0.050 (5) | −0.028 (4) | −0.003 (4) | −0.001 (4) |
C20 | 0.082 (7) | 0.056 (5) | 0.042 (5) | −0.035 (5) | 0.005 (5) | 0.011 (4) |
C21 | 0.027 (3) | 0.025 (3) | 0.034 (4) | −0.002 (3) | 0.014 (3) | 0.001 (3) |
C22 | 0.032 (4) | 0.036 (4) | 0.047 (4) | 0.001 (3) | 0.005 (3) | −0.003 (3) |
C23 | 0.047 (5) | 0.049 (4) | 0.032 (4) | 0.001 (4) | 0.013 (4) | −0.002 (3) |
C24 | 0.040 (4) | 0.031 (4) | 0.049 (5) | 0.004 (3) | 0.017 (4) | −0.005 (3) |
C25 | 0.030 (4) | 0.017 (3) | 0.033 (4) | −0.004 (3) | 0.011 (3) | 0.007 (2) |
C26 | 0.051 (5) | 0.033 (4) | 0.037 (4) | 0.005 (3) | 0.014 (4) | 0.008 (3) |
C27 | 0.031 (4) | 0.032 (4) | 0.044 (4) | 0.001 (3) | 0.012 (3) | 0.008 (3) |
C28 | 0.036 (4) | 0.029 (4) | 0.036 (4) | 0.000 (3) | 0.009 (3) | 0.000 (3) |
C29 | 0.052 (3) | 0.074 (3) | 0.081 (3) | 0.000 (3) | 0.026 (3) | −0.025 (3) |
C30 | 0.052 (3) | 0.074 (3) | 0.081 (3) | 0.000 (3) | 0.026 (3) | −0.025 (3) |
C31 | 0.052 (3) | 0.074 (3) | 0.081 (3) | 0.000 (3) | 0.026 (3) | −0.025 (3) |
C32 | 0.052 (3) | 0.074 (3) | 0.081 (3) | 0.000 (3) | 0.026 (3) | −0.025 (3) |
C33 | 0.017 (3) | 0.041 (4) | 0.063 (5) | 0.008 (3) | 0.002 (3) | 0.004 (4) |
C34 | 0.036 (12) | 0.041 (12) | 0.059 (16) | −0.009 (9) | 0.000 (10) | 0.004 (10) |
C35 | 0.034 (8) | 0.026 (7) | 0.045 (11) | 0.007 (6) | −0.005 (7) | −0.003 (6) |
C36 | 0.033 (8) | 0.057 (11) | 0.038 (9) | 0.010 (8) | −0.003 (7) | −0.005 (8) |
C34A | 0.044 (15) | 0.036 (12) | 0.046 (15) | −0.004 (10) | −0.019 (11) | 0.000 (10) |
C35A | 0.029 (9) | 0.040 (10) | 0.058 (13) | 0.018 (7) | −0.003 (8) | −0.021 (9) |
C36A | 0.028 (9) | 0.072 (16) | 0.069 (15) | 0.001 (9) | −0.012 (9) | 0.033 (13) |
C37 | 0.039 (4) | 0.032 (4) | 0.028 (4) | −0.004 (3) | 0.014 (3) | 0.004 (3) |
C38 | 0.043 (5) | 0.041 (4) | 0.041 (4) | 0.002 (4) | 0.013 (4) | 0.009 (3) |
C39 | 0.049 (5) | 0.035 (4) | 0.050 (5) | 0.001 (4) | 0.026 (4) | 0.014 (3) |
C40 | 0.087 (7) | 0.044 (4) | 0.027 (4) | −0.018 (4) | 0.021 (4) | −0.005 (3) |
C41 | 0.046 (4) | 0.021 (3) | 0.031 (4) | −0.001 (3) | 0.009 (3) | −0.004 (3) |
C42 | 0.051 (5) | 0.031 (4) | 0.059 (5) | 0.005 (4) | 0.021 (4) | −0.002 (3) |
C43 | 0.092 (7) | 0.026 (4) | 0.052 (5) | 0.000 (4) | 0.002 (5) | −0.015 (4) |
C44 | 0.049 (5) | 0.025 (3) | 0.043 (4) | 0.003 (3) | 0.011 (4) | 0.008 (3) |
C45 | 0.040 (3) | 0.106 (4) | 0.068 (3) | −0.020 (3) | −0.002 (2) | −0.009 (3) |
C46 | 0.040 (3) | 0.106 (4) | 0.068 (3) | −0.020 (3) | −0.002 (2) | −0.009 (3) |
C47 | 0.040 (3) | 0.106 (4) | 0.068 (3) | −0.020 (3) | −0.002 (2) | −0.009 (3) |
C48 | 0.040 (3) | 0.106 (4) | 0.068 (3) | −0.020 (3) | −0.002 (2) | −0.009 (3) |
C49 | 0.024 (3) | 0.022 (3) | 0.028 (3) | 0.001 (3) | 0.001 (3) | −0.001 (2) |
C50 | 0.022 (3) | 0.017 (3) | 0.036 (4) | 0.003 (3) | 0.001 (3) | −0.001 (3) |
C51 | 0.022 (3) | 0.019 (3) | 0.028 (3) | −0.007 (3) | 0.001 (3) | 0.000 (2) |
C52 | 0.025 (3) | 0.019 (3) | 0.031 (4) | −0.006 (3) | 0.006 (3) | 0.004 (2) |
C53 | 0.023 (3) | 0.028 (3) | 0.038 (4) | −0.002 (3) | 0.008 (3) | −0.005 (3) |
C54 | 0.030 (4) | 0.021 (3) | 0.033 (4) | −0.004 (3) | 0.011 (3) | −0.004 (3) |
C56 | 0.028 (4) | 0.021 (3) | 0.035 (4) | −0.002 (3) | 0.012 (3) | 0.001 (3) |
C57 | 0.032 (4) | 0.016 (3) | 0.039 (4) | −0.001 (3) | 0.009 (3) | −0.001 (3) |
C58 | 0.019 (3) | 0.020 (3) | 0.029 (3) | −0.001 (3) | 0.006 (3) | −0.003 (2) |
C59 | 0.027 (4) | 0.017 (3) | 0.036 (4) | 0.002 (3) | 0.006 (3) | −0.009 (3) |
C60 | 0.044 (4) | 0.039 (4) | 0.043 (4) | 0.011 (4) | 0.011 (4) | 0.009 (3) |
O13 | 0.036 (3) | 0.024 (2) | 0.030 (3) | 0.001 (2) | 0.007 (2) | 0.0027 (18) |
Geometric parameters (Å, º) top Zn1—N1 | 2.075 (5) | C24—H24A | 0.98 |
Zn1—S2 | 2.2664 (18) | C24—H24B | 0.98 |
Zn1—S1 | 2.2732 (16) | C24—H24C | 0.98 |
Zn1—O1 | 2.357 (4) | C25—C28 | 1.504 (9) |
Zn1—O4 | 2.554 (4) | C25—C27 | 1.515 (10) |
Zn2—N2 | 2.098 (5) | C25—C26 | 1.536 (9) |
Zn2—O13 | 2.156 (5) | C26—H26A | 0.98 |
Zn2—S4 | 2.2627 (16) | C26—H26B | 0.98 |
Zn2—S3 | 2.2704 (17) | C26—H26C | 0.98 |
S1—Si1 | 2.075 (2) | C27—H27A | 0.98 |
S2—Si2 | 2.092 (2) | C27—H27B | 0.98 |
S3—Si3 | 2.091 (2) | C27—H27C | 0.98 |
S4—Si4 | 2.076 (2) | C28—H28A | 0.98 |
Si1—O3 | 1.620 (4) | C28—H28B | 0.98 |
Si1—O2 | 1.633 (5) | C28—H28C | 0.98 |
Si1—O1 | 1.661 (4) | C29—C30 | 1.487 (14) |
Si2—O5 | 1.622 (5) | C29—C31 | 1.510 (14) |
Si2—O6 | 1.630 (4) | C29—C32 | 1.520 (16) |
Si2—O4 | 1.643 (5) | C30—H30A | 0.98 |
Si3—O9 | 1.628 (5) | C30—H30B | 0.98 |
Si3—O8 | 1.630 (5) | C30—H30C | 0.98 |
Si3—O7 | 1.631 (5) | C31—H31A | 0.98 |
Si4—O12 | 1.623 (5) | C31—H31B | 0.98 |
Si4—O11 | 1.626 (4) | C31—H31C | 0.98 |
Si4—O10 | 1.660 (5) | C32—H32A | 0.98 |
O1—C1 | 1.460 (7) | C32—H32B | 0.98 |
O2—C5 | 1.430 (8) | C32—H32C | 0.98 |
O3—C9 | 1.439 (7) | C33—C35 | 1.417 (15) |
O4—C13 | 1.457 (8) | C33—C36A | 1.42 (2) |
O5—C17 | 1.450 (8) | C33—C34A | 1.45 (3) |
O6—C21 | 1.438 (8) | C33—C34 | 1.51 (2) |
O7—C25 | 1.456 (8) | C33—C35A | 1.627 (18) |
O8—C29 | 1.425 (10) | C33—C36 | 1.654 (18) |
O9—C33 | 1.453 (9) | C34—H34A | 0.98 |
O10—C37 | 1.462 (8) | C34—H34B | 0.98 |
O11—C41 | 1.451 (8) | C34—H34C | 0.98 |
O12—C45 | 1.438 (11) | C35—H35A | 0.98 |
N1—C59 | 1.338 (8) | C35—H35B | 0.98 |
N1—C49 | 1.342 (8) | C35—H35C | 0.98 |
N2—C54 | 1.323 (9) | C36—H36A | 0.98 |
N2—C56 | 1.339 (8) | C36—H36B | 0.98 |
C1—C2 | 1.510 (10) | C36—H36C | 0.98 |
C1—C3 | 1.510 (10) | C34A—H34D | 0.98 |
C1—C4 | 1.523 (10) | C34A—H34E | 0.98 |
C2—H2A | 0.98 | C34A—H34F | 0.98 |
C2—H2B | 0.98 | C35A—H35D | 0.98 |
C2—H2C | 0.98 | C35A—H35E | 0.98 |
C3—H3A | 0.98 | C35A—H35F | 0.98 |
C3—H3B | 0.98 | C36A—H36D | 0.98 |
C3—H3C | 0.98 | C36A—H36E | 0.98 |
C4—H4A | 0.98 | C36A—H36F | 0.98 |
C4—H4B | 0.98 | C37—C38 | 1.495 (10) |
C4—H4C | 0.98 | C37—C39 | 1.501 (11) |
C5—C8 | 1.518 (10) | C37—C40 | 1.529 (10) |
C5—C6 | 1.519 (11) | C38—H38A | 0.98 |
C5—C7 | 1.520 (10) | C38—H38B | 0.98 |
C6—H6A | 0.98 | C38—H38C | 0.98 |
C6—H6B | 0.98 | C39—H39A | 0.98 |
C6—H6C | 0.98 | C39—H39B | 0.98 |
C7—H7A | 0.98 | C39—H39C | 0.98 |
C7—H7B | 0.98 | C40—H40A | 0.98 |
C7—H7C | 0.98 | C40—H40B | 0.98 |
C8—H8A | 0.98 | C40—H40C | 0.98 |
C8—H8B | 0.98 | C41—C42 | 1.513 (11) |
C8—H8C | 0.98 | C41—C44 | 1.523 (10) |
C9—C12 | 1.507 (11) | C41—C43 | 1.525 (10) |
C9—C10 | 1.510 (10) | C42—H42A | 0.98 |
C9—C11 | 1.511 (10) | C42—H42B | 0.98 |
C10—H10A | 0.98 | C42—H42C | 0.98 |
C10—H10B | 0.98 | C43—H43A | 0.98 |
C10—H10C | 0.98 | C43—H43B | 0.98 |
C11—H11A | 0.98 | C43—H43C | 0.98 |
C11—H11B | 0.98 | C44—H44A | 0.98 |
C11—H11C | 0.98 | C44—H44B | 0.98 |
C12—H12A | 0.98 | C44—H44C | 0.98 |
C12—H12B | 0.98 | C45—C48 | 1.469 (14) |
C12—H12C | 0.98 | C45—C46 | 1.482 (15) |
C13—C14 | 1.518 (9) | C45—C47 | 1.519 (15) |
C13—C16 | 1.527 (10) | C46—H46A | 0.98 |
C13—C15 | 1.537 (9) | C46—H46B | 0.98 |
C14—H14A | 0.98 | C46—H46C | 0.98 |
C14—H14B | 0.98 | C47—H47A | 0.98 |
C14—H14C | 0.98 | C47—H47B | 0.98 |
C15—H15A | 0.98 | C47—H47C | 0.98 |
C15—H15B | 0.98 | C48—H48A | 0.98 |
C15—H15C | 0.98 | C48—H48B | 0.98 |
C16—H16A | 0.98 | C48—H48C | 0.98 |
C16—H16B | 0.98 | C49—C50 | 1.372 (9) |
C16—H16C | 0.98 | C49—H49 | 0.95 |
C17—C18 | 1.499 (11) | C50—C51 | 1.398 (9) |
C17—C19 | 1.506 (11) | C50—H50 | 0.95 |
C17—C20 | 1.508 (10) | C51—C58 | 1.392 (8) |
C18—H18A | 0.98 | C51—C52 | 1.482 (8) |
C18—H18B | 0.98 | C52—C53 | 1.380 (9) |
C18—H18C | 0.98 | C52—C57 | 1.396 (9) |
C19—H19A | 0.98 | C53—C54 | 1.376 (9) |
C19—H19B | 0.98 | C53—H53 | 0.95 |
C19—H19C | 0.98 | C54—H54 | 0.95 |
C20—H20A | 0.98 | C56—C57 | 1.378 (9) |
C20—H20B | 0.98 | C56—H56 | 0.95 |
C20—H20C | 0.98 | C57—H57 | 0.95 |
C21—C22 | 1.513 (10) | C58—C59 | 1.373 (9) |
C21—C23 | 1.513 (10) | C58—H58 | 0.95 |
C21—C24 | 1.535 (9) | C59—H59 | 0.95 |
C22—H22A | 0.98 | C60—O13 | 1.419 (9) |
C22—H22B | 0.98 | C60—H60A | 0.98 |
C22—H22C | 0.98 | C60—H60B | 0.98 |
C23—H23A | 0.98 | C60—H60C | 0.98 |
C23—H23B | 0.98 | O13—H13A | 0.988 (10) |
C23—H23C | 0.98 | | |
| | | |
N1—Zn1—S2 | 111.39 (14) | H24A—C24—H24B | 109.5 |
N1—Zn1—S1 | 107.81 (15) | C21—C24—H24C | 109.5 |
S2—Zn1—S1 | 139.71 (7) | H24A—C24—H24C | 109.5 |
N1—Zn1—O1 | 92.46 (17) | H24B—C24—H24C | 109.5 |
S2—Zn1—O1 | 108.85 (12) | O7—C25—C28 | 112.0 (5) |
S1—Zn1—O1 | 77.94 (11) | O7—C25—C27 | 106.6 (5) |
N1—Zn1—O4 | 90.91 (17) | C28—C25—C27 | 111.8 (6) |
S2—Zn1—O4 | 74.68 (10) | O7—C25—C26 | 104.9 (5) |
S1—Zn1—O4 | 96.04 (11) | C28—C25—C26 | 110.0 (5) |
O1—Zn1—O4 | 173.77 (14) | C27—C25—C26 | 111.3 (6) |
N2—Zn2—O13 | 93.72 (19) | C25—C26—H26A | 109.5 |
N2—Zn2—S4 | 105.61 (15) | C25—C26—H26B | 109.5 |
O13—Zn2—S4 | 99.79 (13) | H26A—C26—H26B | 109.5 |
N2—Zn2—S3 | 109.24 (15) | C25—C26—H26C | 109.5 |
O13—Zn2—S3 | 100.81 (13) | H26A—C26—H26C | 109.5 |
S4—Zn2—S3 | 137.87 (6) | H26B—C26—H26C | 109.5 |
Si1—S1—Zn1 | 85.98 (7) | C25—C27—H27A | 109.5 |
Si2—S2—Zn1 | 89.35 (8) | C25—C27—H27B | 109.5 |
Si3—S3—Zn2 | 93.88 (8) | H27A—C27—H27B | 109.5 |
Si4—S4—Zn2 | 99.32 (8) | C25—C27—H27C | 109.5 |
O3—Si1—O2 | 105.5 (2) | H27A—C27—H27C | 109.5 |
O3—Si1—O1 | 113.5 (2) | H27B—C27—H27C | 109.5 |
O2—Si1—O1 | 104.0 (2) | C25—C28—H28A | 109.5 |
O3—Si1—S1 | 115.46 (17) | C25—C28—H28B | 109.5 |
O2—Si1—S1 | 116.22 (19) | H28A—C28—H28B | 109.5 |
O1—Si1—S1 | 101.86 (16) | C25—C28—H28C | 109.5 |
O5—Si2—O6 | 104.6 (2) | H28A—C28—H28C | 109.5 |
O5—Si2—O4 | 113.1 (2) | H28B—C28—H28C | 109.5 |
O6—Si2—O4 | 106.3 (2) | O8—C29—C30 | 114.4 (8) |
O5—Si2—S2 | 114.96 (19) | O8—C29—C31 | 106.0 (8) |
O6—Si2—S2 | 115.06 (18) | C30—C29—C31 | 113.8 (9) |
O4—Si2—S2 | 102.83 (17) | O8—C29—C32 | 105.5 (8) |
O9—Si3—O8 | 104.5 (3) | C30—C29—C32 | 107.6 (9) |
O9—Si3—O7 | 112.0 (2) | C31—C29—C32 | 109.2 (9) |
O8—Si3—O7 | 105.8 (2) | C29—C30—H30A | 109.5 |
O9—Si3—S3 | 105.60 (19) | C29—C30—H30B | 109.5 |
O8—Si3—S3 | 112.98 (19) | H30A—C30—H30B | 109.5 |
O7—Si3—S3 | 115.4 (2) | C29—C30—H30C | 109.5 |
O12—Si4—O11 | 114.3 (2) | H30A—C30—H30C | 109.5 |
O12—Si4—O10 | 104.5 (2) | H30B—C30—H30C | 109.5 |
O11—Si4—O10 | 104.8 (2) | C29—C31—H31A | 109.5 |
O12—Si4—S4 | 107.98 (19) | C29—C31—H31B | 109.5 |
O11—Si4—S4 | 112.2 (2) | H31A—C31—H31B | 109.5 |
O10—Si4—S4 | 112.91 (18) | C29—C31—H31C | 109.5 |
C1—O1—Si1 | 130.4 (4) | H31A—C31—H31C | 109.5 |
C1—O1—Zn1 | 133.6 (3) | H31B—C31—H31C | 109.5 |
Si1—O1—Zn1 | 93.64 (18) | C29—C32—H32A | 109.5 |
C5—O2—Si1 | 132.1 (4) | C29—C32—H32B | 109.5 |
C9—O3—Si1 | 134.8 (4) | H32A—C32—H32B | 109.5 |
C13—O4—Si2 | 130.6 (4) | C29—C32—H32C | 109.5 |
C13—O4—Zn1 | 138.0 (4) | H32A—C32—H32C | 109.5 |
Si2—O4—Zn1 | 91.27 (19) | H32B—C32—H32C | 109.5 |
C17—O5—Si2 | 135.3 (4) | C35—C33—C36A | 67.8 (13) |
C21—O6—Si2 | 131.4 (4) | C35—C33—C34A | 134.3 (13) |
C25—O7—Si3 | 132.4 (4) | C36A—C33—C34A | 119.3 (15) |
C29—O8—Si3 | 133.7 (5) | C35—C33—O9 | 111.9 (8) |
C33—O9—Si3 | 131.4 (5) | C36A—C33—O9 | 111.3 (9) |
C37—O10—Si4 | 129.9 (4) | C34A—C33—O9 | 106.5 (11) |
C41—O11—Si4 | 133.4 (4) | C35—C33—C34 | 111.8 (12) |
C45—O12—Si4 | 135.0 (6) | C36A—C33—C34 | 133.8 (14) |
C59—N1—C49 | 118.0 (5) | O9—C33—C34 | 110.8 (11) |
C59—N1—Zn1 | 119.5 (4) | C36A—C33—C35A | 110.0 (13) |
C49—N1—Zn1 | 122.2 (4) | C34A—C33—C35A | 108.0 (13) |
C54—N2—C56 | 118.0 (6) | O9—C33—C35A | 100.0 (8) |
C54—N2—Zn2 | 120.7 (4) | C35—C33—C36 | 106.5 (10) |
C56—N2—Zn2 | 121.2 (4) | C34A—C33—C36 | 80.7 (13) |
O1—C1—C2 | 110.1 (5) | O9—C33—C36 | 111.3 (7) |
O1—C1—C3 | 105.5 (5) | C34—C33—C36 | 104.2 (12) |
C2—C1—C3 | 111.3 (7) | C33—C34—H34A | 109.5 |
O1—C1—C4 | 109.2 (6) | C33—C34—H34B | 109.5 |
C2—C1—C4 | 110.1 (6) | C33—C34—H34C | 109.5 |
C3—C1—C4 | 110.5 (6) | C33—C35—H35A | 109.5 |
C1—C2—H2A | 109.5 | C33—C35—H35B | 109.5 |
C1—C2—H2B | 109.5 | C33—C35—H35C | 109.5 |
H2A—C2—H2B | 109.5 | C33—C36—H36A | 109.5 |
C1—C2—H2C | 109.5 | C33—C36—H36B | 109.5 |
H2A—C2—H2C | 109.5 | C33—C36—H36C | 109.5 |
H2B—C2—H2C | 109.5 | C33—C34A—H34D | 109.5 |
C1—C3—H3A | 109.5 | C33—C34A—H34E | 109.5 |
C1—C3—H3B | 109.5 | H34D—C34A—H34E | 109.5 |
H3A—C3—H3B | 109.5 | C33—C34A—H34F | 109.5 |
C1—C3—H3C | 109.5 | H34D—C34A—H34F | 109.5 |
H3A—C3—H3C | 109.5 | H34E—C34A—H34F | 109.5 |
H3B—C3—H3C | 109.5 | C33—C35A—H35D | 109.5 |
C1—C4—H4A | 109.5 | C33—C35A—H35E | 109.5 |
C1—C4—H4B | 109.5 | H35D—C35A—H35E | 109.5 |
H4A—C4—H4B | 109.5 | C33—C35A—H35F | 109.5 |
C1—C4—H4C | 109.5 | H35D—C35A—H35F | 109.5 |
H4A—C4—H4C | 109.5 | H35E—C35A—H35F | 109.5 |
H4B—C4—H4C | 109.5 | C33—C36A—H36D | 109.5 |
O2—C5—C8 | 111.1 (5) | C33—C36A—H36E | 109.5 |
O2—C5—C6 | 108.7 (6) | H36D—C36A—H36E | 109.5 |
C8—C5—C6 | 110.9 (6) | C33—C36A—H36F | 109.5 |
O2—C5—C7 | 105.5 (5) | H36D—C36A—H36F | 109.5 |
C8—C5—C7 | 110.9 (7) | H36E—C36A—H36F | 109.5 |
C6—C5—C7 | 109.6 (7) | O10—C37—C38 | 105.1 (5) |
C5—C6—H6A | 109.5 | O10—C37—C39 | 110.6 (6) |
C5—C6—H6B | 109.5 | C38—C37—C39 | 111.1 (6) |
H6A—C6—H6B | 109.5 | O10—C37—C40 | 108.6 (5) |
C5—C6—H6C | 109.5 | C38—C37—C40 | 109.2 (7) |
H6A—C6—H6C | 109.5 | C39—C37—C40 | 111.8 (7) |
H6B—C6—H6C | 109.5 | C37—C38—H38A | 109.5 |
C5—C7—H7A | 109.5 | C37—C38—H38B | 109.5 |
C5—C7—H7B | 109.5 | H38A—C38—H38B | 109.5 |
H7A—C7—H7B | 109.5 | C37—C38—H38C | 109.5 |
C5—C7—H7C | 109.5 | H38A—C38—H38C | 109.5 |
H7A—C7—H7C | 109.5 | H38B—C38—H38C | 109.5 |
H7B—C7—H7C | 109.5 | C37—C39—H39A | 109.5 |
C5—C8—H8A | 109.5 | C37—C39—H39B | 109.5 |
C5—C8—H8B | 109.5 | H39A—C39—H39B | 109.5 |
H8A—C8—H8B | 109.5 | C37—C39—H39C | 109.5 |
C5—C8—H8C | 109.5 | H39A—C39—H39C | 109.5 |
H8A—C8—H8C | 109.5 | H39B—C39—H39C | 109.5 |
H8B—C8—H8C | 109.5 | C37—C40—H40A | 109.5 |
O3—C9—C12 | 110.7 (5) | C37—C40—H40B | 109.5 |
O3—C9—C10 | 104.9 (5) | H40A—C40—H40B | 109.5 |
C12—C9—C10 | 111.4 (7) | C37—C40—H40C | 109.5 |
O3—C9—C11 | 108.7 (6) | H40A—C40—H40C | 109.5 |
C12—C9—C11 | 110.0 (6) | H40B—C40—H40C | 109.5 |
C10—C9—C11 | 110.8 (6) | O11—C41—C42 | 109.1 (5) |
C9—C10—H10A | 109.5 | O11—C41—C44 | 110.7 (5) |
C9—C10—H10B | 109.5 | C42—C41—C44 | 110.6 (7) |
H10A—C10—H10B | 109.5 | O11—C41—C43 | 104.6 (6) |
C9—C10—H10C | 109.5 | C42—C41—C43 | 111.4 (7) |
H10A—C10—H10C | 109.5 | C44—C41—C43 | 110.4 (6) |
H10B—C10—H10C | 109.5 | C41—C42—H42A | 109.5 |
C9—C11—H11A | 109.5 | C41—C42—H42B | 109.5 |
C9—C11—H11B | 109.5 | H42A—C42—H42B | 109.5 |
H11A—C11—H11B | 109.5 | C41—C42—H42C | 109.5 |
C9—C11—H11C | 109.5 | H42A—C42—H42C | 109.5 |
H11A—C11—H11C | 109.5 | H42B—C42—H42C | 109.5 |
H11B—C11—H11C | 109.5 | C41—C43—H43A | 109.5 |
C9—C12—H12A | 109.5 | C41—C43—H43B | 109.5 |
C9—C12—H12B | 109.5 | H43A—C43—H43B | 109.5 |
H12A—C12—H12B | 109.5 | C41—C43—H43C | 109.5 |
C9—C12—H12C | 109.5 | H43A—C43—H43C | 109.5 |
H12A—C12—H12C | 109.5 | H43B—C43—H43C | 109.5 |
H12B—C12—H12C | 109.5 | C41—C44—H44A | 109.5 |
O4—C13—C14 | 106.1 (5) | C41—C44—H44B | 109.5 |
O4—C13—C16 | 110.1 (5) | H44A—C44—H44B | 109.5 |
C14—C13—C16 | 110.4 (6) | C41—C44—H44C | 109.5 |
O4—C13—C15 | 107.6 (5) | H44A—C44—H44C | 109.5 |
C14—C13—C15 | 110.9 (6) | H44B—C44—H44C | 109.5 |
C16—C13—C15 | 111.5 (6) | O12—C45—C48 | 113.2 (8) |
C13—C14—H14A | 109.5 | O12—C45—C46 | 106.5 (8) |
C13—C14—H14B | 109.5 | C48—C45—C46 | 110.7 (10) |
H14A—C14—H14B | 109.5 | O12—C45—C47 | 106.0 (8) |
C13—C14—H14C | 109.5 | C48—C45—C47 | 113.8 (9) |
H14A—C14—H14C | 109.5 | C46—C45—C47 | 106.1 (9) |
H14B—C14—H14C | 109.5 | C45—C46—H46A | 109.5 |
C13—C15—H15A | 109.5 | C45—C46—H46B | 109.5 |
C13—C15—H15B | 109.5 | H46A—C46—H46B | 109.5 |
H15A—C15—H15B | 109.5 | C45—C46—H46C | 109.5 |
C13—C15—H15C | 109.5 | H46A—C46—H46C | 109.5 |
H15A—C15—H15C | 109.5 | H46B—C46—H46C | 109.5 |
H15B—C15—H15C | 109.5 | C45—C47—H47A | 109.5 |
C13—C16—H16A | 109.5 | C45—C47—H47B | 109.5 |
C13—C16—H16B | 109.5 | H47A—C47—H47B | 109.5 |
H16A—C16—H16B | 109.5 | C45—C47—H47C | 109.5 |
C13—C16—H16C | 109.5 | H47A—C47—H47C | 109.5 |
H16A—C16—H16C | 109.5 | H47B—C47—H47C | 109.5 |
H16B—C16—H16C | 109.5 | C45—C48—H48A | 109.5 |
O5—C17—C18 | 110.9 (6) | C45—C48—H48B | 109.5 |
O5—C17—C19 | 109.3 (6) | H48A—C48—H48B | 109.5 |
C18—C17—C19 | 112.4 (7) | C45—C48—H48C | 109.5 |
O5—C17—C20 | 104.4 (6) | H48A—C48—H48C | 109.5 |
C18—C17—C20 | 109.7 (8) | H48B—C48—H48C | 109.5 |
C19—C17—C20 | 109.9 (7) | N1—C49—C50 | 122.9 (6) |
C17—C18—H18A | 109.5 | N1—C49—H49 | 118.5 |
C17—C18—H18B | 109.5 | C50—C49—H49 | 118.5 |
H18A—C18—H18B | 109.5 | C49—C50—C51 | 119.4 (5) |
C17—C18—H18C | 109.5 | C49—C50—H50 | 120.3 |
H18A—C18—H18C | 109.5 | C51—C50—H50 | 120.3 |
H18B—C18—H18C | 109.5 | C58—C51—C50 | 117.2 (5) |
C17—C19—H19A | 109.5 | C58—C51—C52 | 120.9 (6) |
C17—C19—H19B | 109.5 | C50—C51—C52 | 121.7 (5) |
H19A—C19—H19B | 109.5 | C53—C52—C57 | 117.5 (6) |
C17—C19—H19C | 109.5 | C53—C52—C51 | 121.6 (6) |
H19A—C19—H19C | 109.5 | C57—C52—C51 | 120.7 (6) |
H19B—C19—H19C | 109.5 | C54—C53—C52 | 119.8 (6) |
C17—C20—H20A | 109.5 | C54—C53—H53 | 120.1 |
C17—C20—H20B | 109.5 | C52—C53—H53 | 120.1 |
H20A—C20—H20B | 109.5 | N2—C54—C53 | 122.9 (6) |
C17—C20—H20C | 109.5 | N2—C54—H54 | 118.6 |
H20A—C20—H20C | 109.5 | C53—C54—H54 | 118.6 |
H20B—C20—H20C | 109.5 | N2—C56—C57 | 122.9 (6) |
O6—C21—C22 | 110.7 (5) | N2—C56—H56 | 118.6 |
O6—C21—C23 | 110.3 (6) | C57—C56—H56 | 118.6 |
C22—C21—C23 | 111.0 (6) | C56—C57—C52 | 118.9 (6) |
O6—C21—C24 | 105.2 (5) | C56—C57—H57 | 120.6 |
C22—C21—C24 | 110.0 (6) | C52—C57—H57 | 120.6 |
C23—C21—C24 | 109.5 (6) | C59—C58—C51 | 119.9 (6) |
C21—C22—H22A | 109.5 | C59—C58—H58 | 120 |
C21—C22—H22B | 109.5 | C51—C58—H58 | 120 |
H22A—C22—H22B | 109.5 | N1—C59—C58 | 122.5 (5) |
C21—C22—H22C | 109.5 | N1—C59—H59 | 118.7 |
H22A—C22—H22C | 109.5 | C58—C59—H59 | 118.7 |
H22B—C22—H22C | 109.5 | O13—C60—H60A | 109.5 |
C21—C23—H23A | 109.5 | O13—C60—H60B | 109.5 |
C21—C23—H23B | 109.5 | H60A—C60—H60B | 109.5 |
H23A—C23—H23B | 109.5 | O13—C60—H60C | 109.5 |
C21—C23—H23C | 109.5 | H60A—C60—H60C | 109.5 |
H23A—C23—H23C | 109.5 | H60B—C60—H60C | 109.5 |
H23B—C23—H23C | 109.5 | C60—O13—Zn2 | 124.5 (4) |
C21—C24—H24A | 109.5 | C60—O13—H13A | 111 (5) |
C21—C24—H24B | 109.5 | Zn2—O13—H13A | 117 (4) |
| | | |
N1—Zn1—S1—Si1 | 84.07 (16) | O4—Zn1—N1—C59 | −102.5 (5) |
S2—Zn1—S1—Si1 | −109.63 (11) | S2—Zn1—N1—C49 | −2.2 (5) |
O1—Zn1—S1—Si1 | −4.64 (12) | S1—Zn1—N1—C49 | 168.3 (4) |
O4—Zn1—S1—Si1 | 176.98 (12) | O1—Zn1—N1—C49 | −113.6 (5) |
N1—Zn1—S2—Si2 | 92.88 (17) | O4—Zn1—N1—C49 | 71.6 (5) |
S1—Zn1—S2—Si2 | −73.10 (12) | O13—Zn2—N2—C54 | −87.8 (5) |
O1—Zn1—S2—Si2 | −166.61 (12) | S4—Zn2—N2—C54 | 13.4 (5) |
O4—Zn1—S2—Si2 | 8.02 (11) | S3—Zn2—N2—C54 | 169.4 (5) |
N2—Zn2—S3—Si3 | −73.62 (17) | O13—Zn2—N2—C56 | 96.7 (5) |
O13—Zn2—S3—Si3 | −171.46 (13) | S4—Zn2—N2—C56 | −162.1 (4) |
S4—Zn2—S3—Si3 | 70.56 (12) | S3—Zn2—N2—C56 | −6.1 (5) |
N2—Zn2—S4—Si4 | −141.77 (16) | Si1—O1—C1—C2 | −42.1 (8) |
O13—Zn2—S4—Si4 | −45.08 (15) | Zn1—O1—C1—C2 | 160.4 (5) |
S3—Zn2—S4—Si4 | 73.25 (12) | Si1—O1—C1—C3 | −162.2 (5) |
Zn1—S1—Si1—O3 | 130.0 (2) | Zn1—O1—C1—C3 | 40.3 (8) |
Zn1—S1—Si1—O2 | −105.65 (18) | Si1—O1—C1—C4 | 79.0 (6) |
Zn1—S1—Si1—O1 | 6.58 (17) | Zn1—O1—C1—C4 | −78.5 (7) |
Zn1—S2—Si2—O5 | 111.0 (2) | Si1—O2—C5—C8 | 40.1 (9) |
Zn1—S2—Si2—O6 | −127.46 (19) | Si1—O2—C5—C6 | −82.2 (7) |
Zn1—S2—Si2—O4 | −12.39 (17) | Si1—O2—C5—C7 | 160.4 (6) |
Zn2—S3—Si3—O9 | 10.0 (2) | Si1—O3—C9—C12 | −44.4 (9) |
Zn2—S3—Si3—O8 | 123.7 (2) | Si1—O3—C9—C10 | −164.8 (6) |
Zn2—S3—Si3—O7 | −114.32 (19) | Si1—O3—C9—C11 | 76.6 (7) |
Zn2—S4—Si4—O12 | −49.28 (19) | Si2—O4—C13—C14 | −158.0 (5) |
Zn2—S4—Si4—O11 | −176.06 (18) | Zn1—O4—C13—C14 | 28.1 (8) |
Zn2—S4—Si4—O10 | 65.8 (2) | Si2—O4—C13—C16 | −38.6 (7) |
O3—Si1—O1—C1 | 65.0 (6) | Zn1—O4—C13—C16 | 147.6 (5) |
O2—Si1—O1—C1 | −49.0 (6) | Si2—O4—C13—C15 | 83.2 (6) |
S1—Si1—O1—C1 | −170.2 (5) | Zn1—O4—C13—C15 | −90.7 (6) |
O3—Si1—O1—Zn1 | −131.1 (2) | Si2—O5—C17—C18 | −43.3 (9) |
O2—Si1—O1—Zn1 | 114.8 (2) | Si2—O5—C17—C19 | 81.1 (8) |
S1—Si1—O1—Zn1 | −6.34 (16) | Si2—O5—C17—C20 | −161.4 (6) |
N1—Zn1—O1—C1 | 61.1 (5) | Si2—O6—C21—C22 | 40.5 (8) |
S2—Zn1—O1—C1 | −52.5 (5) | Si2—O6—C21—C23 | −82.7 (7) |
S1—Zn1—O1—C1 | 168.8 (5) | Si2—O6—C21—C24 | 159.3 (5) |
N1—Zn1—O1—Si1 | −101.9 (2) | Si3—O7—C25—C28 | 33.0 (8) |
S2—Zn1—O1—Si1 | 144.49 (14) | Si3—O7—C25—C27 | −89.5 (6) |
S1—Zn1—O1—Si1 | 5.79 (15) | Si3—O7—C25—C26 | 152.3 (5) |
O3—Si1—O2—C5 | 45.9 (6) | Si3—O8—C29—C30 | −8.7 (14) |
O1—Si1—O2—C5 | 165.6 (6) | Si3—O8—C29—C31 | −134.9 (7) |
S1—Si1—O2—C5 | −83.4 (6) | Si3—O8—C29—C32 | 109.3 (8) |
O2—Si1—O3—C9 | −163.3 (6) | Si3—O9—C33—C35 | 103.0 (10) |
O1—Si1—O3—C9 | 83.5 (6) | Si3—O9—C33—C36A | 29.3 (15) |
S1—Si1—O3—C9 | −33.6 (6) | Si3—O9—C33—C34A | −102.3 (13) |
O5—Si2—O4—C13 | 70.5 (5) | Si3—O9—C33—C34 | −131.5 (11) |
O6—Si2—O4—C13 | −43.7 (5) | Si3—O9—C33—C35A | 145.4 (9) |
S2—Si2—O4—C13 | −164.9 (5) | Si3—O9—C33—C36 | −16.0 (11) |
O5—Si2—O4—Zn1 | −113.6 (2) | Si4—O10—C37—C38 | −163.9 (5) |
O6—Si2—O4—Zn1 | 132.24 (19) | Si4—O10—C37—C39 | −43.8 (8) |
S2—Si2—O4—Zn1 | 10.98 (15) | Si4—O10—C37—C40 | 79.3 (8) |
N1—Zn1—O4—C13 | 53.2 (5) | Si4—O11—C41—C42 | −84.6 (7) |
S2—Zn1—O4—C13 | 165.1 (5) | Si4—O11—C41—C44 | 37.3 (9) |
S1—Zn1—O4—C13 | −54.9 (5) | Si4—O11—C41—C43 | 156.2 (6) |
N1—Zn1—O4—Si2 | −122.2 (2) | Si4—O12—C45—C48 | 17.0 (14) |
S2—Zn1—O4—Si2 | −10.24 (14) | Si4—O12—C45—C46 | −104.8 (9) |
S1—Zn1—O4—Si2 | 129.79 (16) | Si4—O12—C45—C47 | 142.5 (7) |
O6—Si2—O5—C17 | −170.3 (6) | C59—N1—C49—C50 | 2.3 (9) |
O4—Si2—O5—C17 | 74.6 (7) | Zn1—N1—C49—C50 | −171.9 (5) |
S2—Si2—O5—C17 | −43.1 (7) | N1—C49—C50—C51 | 0.3 (10) |
O5—Si2—O6—C21 | 38.7 (6) | C49—C50—C51—C58 | −3.2 (9) |
O4—Si2—O6—C21 | 158.6 (5) | C49—C50—C51—C52 | 172.0 (6) |
S2—Si2—O6—C21 | −88.4 (5) | C58—C51—C52—C53 | 146.2 (7) |
O9—Si3—O7—C25 | −80.1 (6) | C50—C51—C52—C53 | −28.8 (10) |
O8—Si3—O7—C25 | 166.6 (5) | C58—C51—C52—C57 | −30.0 (9) |
S3—Si3—O7—C25 | 40.9 (6) | C50—C51—C52—C57 | 155.1 (6) |
O9—Si3—O8—C29 | −177.0 (8) | C57—C52—C53—C54 | 1.8 (10) |
O7—Si3—O8—C29 | −58.6 (8) | C51—C52—C53—C54 | −174.5 (6) |
S3—Si3—O8—C29 | 68.7 (8) | C56—N2—C54—C53 | −2.4 (10) |
O8—Si3—O9—C33 | 59.0 (6) | Zn2—N2—C54—C53 | −178.0 (5) |
O7—Si3—O9—C33 | −55.1 (6) | C52—C53—C54—N2 | 0.3 (10) |
S3—Si3—O9—C33 | 178.5 (5) | C54—N2—C56—C57 | 2.3 (9) |
O12—Si4—O10—C37 | −159.1 (5) | Zn2—N2—C56—C57 | 178.0 (5) |
O11—Si4—O10—C37 | −38.6 (6) | N2—C56—C57—C52 | −0.2 (10) |
S4—Si4—O10—C37 | 83.8 (5) | C53—C52—C57—C56 | −1.8 (10) |
O12—Si4—O11—C41 | −80.9 (6) | C51—C52—C57—C56 | 174.5 (6) |
O10—Si4—O11—C41 | 165.3 (6) | C50—C51—C58—C59 | 3.6 (9) |
S4—Si4—O11—C41 | 42.4 (6) | C52—C51—C58—C59 | −171.6 (6) |
O11—Si4—O12—C45 | −62.1 (9) | C49—N1—C59—C58 | −1.9 (9) |
O10—Si4—O12—C45 | 51.9 (9) | Zn1—N1—C59—C58 | 172.5 (5) |
S4—Si4—O12—C45 | 172.3 (8) | C51—C58—C59—N1 | −1.1 (10) |
S2—Zn1—N1—C59 | −176.4 (4) | N2—Zn2—O13—C60 | −92.0 (5) |
S1—Zn1—N1—C59 | −5.9 (5) | S4—Zn2—O13—C60 | 161.5 (5) |
O1—Zn1—N1—C59 | 72.3 (5) | S3—Zn2—O13—C60 | 18.4 (5) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13A···O10 | 0.99 (1) | 1.86 (4) | 2.771 (6) | 151 (6) |
Experimental details
Crystal data |
Chemical formula | [Zn2(C12H27O3SSi)4(C10H8N2)(CH4O)] |
Mr | 1436.91 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 120 |
a, b, c (Å) | 9.5897 (2), 36.8378 (11), 22.7611 (5) |
β (°) | 99.127 (2) |
V (Å3) | 7938.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.82 |
Crystal size (mm) | 0.31 × 0.12 × 0.10 |
|
Data collection |
Diffractometer | Oxford Diffraction KM-4-CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15025, 9143, 8015 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.596 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.126, 1.19 |
No. of reflections | 9143 |
No. of parameters | 793 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.13, −0.66 |
Absolute structure | Flack (1983); 2104 Friedel pairs |
Absolute structure parameter | 0.462 (16) |
Selected geometric parameters (Å, º) topZn1—N1 | 2.075 (5) | Zn2—S4 | 2.2627 (16) |
Zn1—S2 | 2.2664 (18) | Zn2—S3 | 2.2704 (17) |
Zn1—S1 | 2.2732 (16) | S1—Si1 | 2.075 (2) |
Zn1—O1 | 2.357 (4) | S2—Si2 | 2.092 (2) |
Zn1—O4 | 2.554 (4) | S3—Si3 | 2.091 (2) |
Zn2—N2 | 2.098 (5) | S4—Si4 | 2.076 (2) |
Zn2—O13 | 2.156 (5) | | |
| | | |
N1—Zn1—S2 | 111.39 (14) | N2—Zn2—O13 | 93.72 (19) |
N1—Zn1—S1 | 107.81 (15) | N2—Zn2—S4 | 105.61 (15) |
S2—Zn1—S1 | 139.71 (7) | O13—Zn2—S4 | 99.79 (13) |
N1—Zn1—O1 | 92.46 (17) | N2—Zn2—S3 | 109.24 (15) |
S2—Zn1—O1 | 108.85 (12) | O13—Zn2—S3 | 100.81 (13) |
S1—Zn1—O1 | 77.94 (11) | S4—Zn2—S3 | 137.87 (6) |
N1—Zn1—O4 | 90.91 (17) | Si1—S1—Zn1 | 85.98 (7) |
S2—Zn1—O4 | 74.68 (10) | Si2—S2—Zn1 | 89.35 (8) |
S1—Zn1—O4 | 96.04 (11) | Si3—S3—Zn2 | 93.88 (8) |
O1—Zn1—O4 | 173.77 (14) | Si4—S4—Zn2 | 99.32 (8) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13A···O10 | 0.99 (1) | 1.86 (4) | 2.771 (6) | 151 (6) |
Acknowledgements
This work was undertaken with financial support from the Polish State Committee, grant No. 3 T09A 12028.
References
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Two different coordination patterns are observed for zinc atoms in the title binuclear complex. Atom Zn1 is pentacoordinated by two O,S–chelating tri-tert-butoxysilanethiolate moieties and one N atom of a 4,4'-bipyridine ligand. Atom Zn2 is tetrahedrally coordinated by two tri-tert-butoxysilanethiolate anions acting as monodentate S-ligands, methanol oxygen and the other N of the 4,4'-bipyridine ligand (Table 1). This non-symmetric coordination results in a significant distortion of the pyridine rings of the 4,4'-bipyridine ligand; they are not only twisted [torsion angle C50—C51—C52—C53 = -28.8 (10)° and C58—C51—C52—C57 - 30.0 (9)°] but also bent [dihedral angle 31.7 (3)°] as well. The system is chiral and twinned by inversion with the Flack parameter of 0.462 (16) indicating almost equal shares of two crystal domains.
Coordination of methanol on zinc is strengthened by an intramolecular O—H···O hydrogen bonding with one of the adjacent tert-butoxy groups (Fig. 1).