Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104001441/na1638sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104001441/na1638Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104001441/na1638IIsup3.hkl |
CCDC references: 235324; 235325
For the preparation of (I), a stirred solution of zinc di-n-butyl dithiocarbamate in ethanol was treated with a solution of 1,10-phenanthroline (2.2 mole equivalent) in ethanol at ambient temperature. After addition of water, a yellow precipitate was collected, which was recrystallized from ethanol/water (Ratio?). Yellow crystals of (I) were obtained (m.p. 461–462 K). Spectroscopic analysis: IR (ν, cm−1): 3050, 2970, 2925, 2860, 1625, 1595, 1570, 1515, 1500, 1470, 1465, 1425, 1405, 1370, 1355, 1350, 1305, 1300, 1290, 1255, 1240, 1255, 1210, 1195, 1180, 1140, 1105, 1090, 1045, 990, 955, 865, 850, 775, 740, 730, 720. For the preparation of (II), di-n-hexylamine (1.0 mole equivalent) and carbon disulfide (1.2 mole equivalent) were added to a stirred aqueous solution of sodium hydroxide (1.1 mole equivalent). The mixture was kept at 273 K for 30 min and then allowed to reach ambient temperature. An aqueous solution of calcium chloride (0.7 mole equivalent) was then added, followed by the addition of a solution of 1,10-phenanthroline (2.2 mole equivalent). The yellow precipitate was recrystallized from ethanol/water (Ratio?). Yellow crystals of (II) were obtained (m.p. 441 K). Spectroscopic analysis: IR (ν, cm−1): 3010, 2940, 2910, 2850, 1610, 1580, 1575, 1565, 1505, 1465, 1415, 1405, 1360, 1250, 1240, 1205, 1175, 1130, 1100, 1085, 980, 950, 940, 925, 885, 845, 830, 800, 725, 720, 690.
The crystal structure of (I) contains one ethanol molecule per unit cell. Because of the very short distances between the centres of symmetry-related molecules, all ethanol atoms were given the occupation factor 0.5. H atoms of (I) and (II) were positioned corresponding to their geometrical conditions and refined using the riding model. The hydroxyl H atom of the ethanol molecule in (I) could not be located.
For both compounds, data collection: CAD-4 Operations Manual (Enraf-Nonius, 1977); cell refinement: CAD-4 Operations Manual; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Sheldrick, 1999); software used to prepare material for publication: SHELXL97.
| Fig. 1. The molecular structure of (I) (top) and (II) (bottom), showing 30% probability displacement ellipsoids. The ethanol molecule in (I) and all H atoms have been omitted for clarity. |
[Zn(C9H18NS2)2(C12H8N2)]·0.5C2H6O | Z = 2 |
Mr = 677.34 | F(000) = 718 |
Triclinic, P1 | Dx = 1.242 Mg m−3 |
a = 10.006 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.347 (2) Å | Cell parameters from 25 reflections |
c = 15.531 (2) Å | θ = 12–20° |
α = 103.71 (1)° | µ = 0.94 mm−1 |
β = 102.78 (2)° | T = 293 K |
γ = 108.37 (2)° | Prismatic, yellow |
V = 1811.2 (8) Å3 | 0.32 × 0.29 × 0.28 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.7° |
Graphite monochromator | h = −11→11 |
2θ/ω scans | k = −15→15 |
6383 measured reflections | l = 0→18 |
6383 independent reflections | 3 standard reflections every 120 min |
5232 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.21 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
6383 reflections | (Δ/σ)max = 0.010 |
379 parameters | Δρmax = 0.79 e Å−3 |
2 restraints | Δρmin = −0.28 e Å−3 |
[Zn(C9H18NS2)2(C12H8N2)]·0.5C2H6O | γ = 108.37 (2)° |
Mr = 677.34 | V = 1811.2 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.006 (4) Å | Mo Kα radiation |
b = 13.347 (2) Å | µ = 0.94 mm−1 |
c = 15.531 (2) Å | T = 293 K |
α = 103.71 (1)° | 0.32 × 0.29 × 0.28 mm |
β = 102.78 (2)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
6383 measured reflections | 3 standard reflections every 120 min |
6383 independent reflections | intensity decay: 0.4% |
5232 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.043 | 2 restraints |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.21 | Δρmax = 0.79 e Å−3 |
6383 reflections | Δρmin = −0.28 e Å−3 |
379 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. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn | 0.20315 (3) | 0.11471 (2) | 0.837087 (19) | 0.05226 (15) | |
S15 | 0.38292 (8) | 0.29624 (6) | 0.95480 (5) | 0.05837 (19) | |
S16 | 0.09494 (8) | 0.16306 (6) | 0.96457 (5) | 0.0637 (2) | |
S17 | 0.08974 (10) | 0.16938 (9) | 0.70791 (7) | 0.0863 (3) | |
S18 | −0.03409 (11) | −0.05297 (8) | 0.71985 (6) | 0.0808 (3) | |
N1 | 0.3993 (3) | 0.1113 (2) | 0.78585 (16) | 0.0585 (5) | |
N14 | 0.2711 (2) | −0.00980 (17) | 0.88136 (15) | 0.0518 (5) | |
C2 | 0.4662 (4) | 0.1763 (3) | 0.7416 (2) | 0.0722 (7) | |
H1 | 0.4252 | 0.2245 | 0.7232 | 0.087* | |
C3 | 0.5946 (5) | 0.1745 (4) | 0.7224 (3) | 0.0891 (10) | |
H2 | 0.6375 | 0.2206 | 0.6912 | 0.107* | |
C4 | 0.6588 (4) | 0.1049 (3) | 0.7493 (3) | 0.0822 (9) | |
H3 | 0.7458 | 0.1042 | 0.7377 | 0.099* | |
C5 | 0.5893 (3) | 0.0349 (3) | 0.7946 (2) | 0.0675 (7) | |
C6 | 0.4622 (3) | 0.0439 (2) | 0.81222 (18) | 0.0578 (6) | |
C7 | 0.6419 (4) | −0.0443 (3) | 0.8229 (2) | 0.0765 (8) | |
H4 | 0.7265 | −0.0503 | 0.8109 | 0.092* | |
C8 | 0.5733 (4) | −0.1094 (3) | 0.8659 (2) | 0.0684 (7) | |
H5 | 0.6098 | −0.1604 | 0.8828 | 0.082* | |
C9 | 0.4449 (3) | −0.1012 (2) | 0.88596 (19) | 0.0564 (6) | |
C10 | 0.3895 (3) | −0.0254 (2) | 0.85984 (16) | 0.0506 (5) | |
C11 | 0.3687 (3) | −0.1662 (2) | 0.9326 (2) | 0.0648 (7) | |
H6 | 0.3995 | −0.2200 | 0.9488 | 0.078* | |
C12 | 0.2489 (3) | −0.1507 (2) | 0.9544 (2) | 0.0657 (7) | |
H7 | 0.1989 | −0.1922 | 0.9862 | 0.079* | |
C13 | 0.2051 (3) | −0.0696 (2) | 0.9268 (2) | 0.0587 (6) | |
H8 | 0.1249 | −0.0580 | 0.9417 | 0.070* | |
C19 | 0.2559 (3) | 0.2825 (2) | 1.0139 (2) | 0.0574 (6) | |
C21 | −0.0386 (3) | 0.0370 (3) | 0.6598 (2) | 0.0666 (7) | |
N20 | 0.2809 (3) | 0.3577 (2) | 1.09434 (19) | 0.0794 (8) | |
C23 | 0.4155 (5) | 0.4587 (4) | 1.1339 (3) | 0.0903 (10) | |
H9 | 0.3953 | 0.5201 | 1.1681 | 0.108* | |
H10 | 0.4499 | 0.4784 | 1.0842 | 0.108* | |
C24 | 0.5349 (6) | 0.4389 (4) | 1.1997 (4) | 0.1066 (14) | |
H11 | 0.4935 | 0.4041 | 1.2411 | 0.128* | |
H12 | 0.5702 | 0.3890 | 1.1636 | 0.128* | |
C25 | 0.6632 (7) | 0.5497 (5) | 1.2567 (4) | 0.1314 (19) | |
H13 | 0.6267 | 0.6020 | 1.2885 | 0.158* | |
H14 | 0.7106 | 0.5814 | 1.2158 | 0.158* | |
C26 | 0.7719 (6) | 0.5309 (5) | 1.3261 (4) | 0.1173 (15) | |
H15 | 0.8096 | 0.4807 | 1.2941 | 0.141* | |
H16 | 0.7241 | 0.4989 | 1.3659 | 0.141* | |
H17 | 0.8526 | 0.6010 | 1.3632 | 0.141* | |
C27 | 0.1589 (6) | 0.3612 (4) | 1.1349 (3) | 0.1045 (13) | |
H18 | 0.1547 | 0.4347 | 1.1464 | 0.125* | |
H19 | 0.0640 | 0.3064 | 1.0910 | 0.125* | |
C28 | 0.1886 (7) | 0.3363 (5) | 1.2247 (5) | 0.1249 (17) | |
H20 | 0.2846 | 0.3900 | 1.2680 | 0.150* | |
H21 | 0.1903 | 0.2621 | 1.2129 | 0.150* | |
C29 | 0.0689 (8) | 0.3427 (6) | 1.2664 (4) | 0.148 (2) | |
H22 | −0.0124 | 0.3463 | 1.2214 | 0.177* | |
H23 | 0.0305 | 0.2772 | 1.2843 | 0.177* | |
C30 | 0.1373 (6) | 0.4466 (5) | 1.3509 (4) | 0.1218 (17) | |
H24 | 0.1905 | 0.5089 | 1.3345 | 0.146* | |
H25 | 0.2047 | 0.4365 | 1.3994 | 0.146* | |
H26 | 0.0604 | 0.4609 | 1.3728 | 0.146* | |
N22 | −0.1441 (3) | 0.0058 (3) | 0.5771 (2) | 0.0932 (10) | |
C31 | −0.1295 (6) | 0.0702 (5) | 0.5153 (4) | 0.1185 (16) | |
H27 | −0.1764 | 0.0211 | 0.4508 | 0.142* | |
H28 | −0.0253 | 0.1105 | 0.5247 | 0.142* | |
C32 | −0.2035 (7) | 0.1515 (5) | 0.5360 (5) | 0.1236 (17) | |
H29 | −0.1695 | 0.1917 | 0.6026 | 0.148* | |
H30 | −0.3106 | 0.1121 | 0.5154 | 0.148* | |
C33 | −0.1598 (7) | 0.2338 (5) | 0.4817 (4) | 0.1269 (18) | |
H31 | −0.1810 | 0.2993 | 0.5052 | 0.152* | |
H32 | −0.0543 | 0.2581 | 0.4899 | 0.152* | |
C34 | −0.2471 (8) | 0.1752 (5) | 0.3810 (4) | 0.1304 (18) | |
H33 | −0.1817 | 0.1637 | 0.3463 | 0.156* | |
H34 | −0.2955 | 0.2199 | 0.3582 | 0.156* | |
H35 | −0.3204 | 0.1042 | 0.3734 | 0.156* | |
C35 | −0.2319 (8) | −0.1154 (6) | 0.5254 (5) | 0.144 (2) | |
H36 | −0.2435 | −0.1316 | 0.4593 | 0.173* | |
H37 | −0.1824 | −0.1598 | 0.5493 | 0.173* | |
C36 | −0.3760 (11) | −0.1407 (8) | 0.5397 (7) | 0.177 (3) | |
H38 | −0.4268 | −0.0979 | 0.5145 | 0.212* | |
H39 | −0.3647 | −0.1234 | 0.6059 | 0.212* | |
C37 | −0.4652 (9) | −0.2696 (9) | 0.4863 (6) | 0.186 (4) | |
H40 | −0.5697 | −0.2848 | 0.4595 | 0.224* | |
H41 | −0.4281 | −0.2942 | 0.4359 | 0.224* | |
C38 | −0.4469 (10) | −0.3297 (7) | 0.5528 (7) | 0.183 (3) | |
H42 | −0.3662 | −0.3533 | 0.5502 | 0.219* | |
H43 | −0.5369 | −0.3941 | 0.5368 | 0.219* | |
H44 | −0.4257 | −0.2812 | 0.6149 | 0.219* | |
O1E | −0.0939 (10) | 0.4038 (5) | 0.9465 (5) | 0.121 (3) | 0.50 |
C1E | 0.0417 (15) | 0.4221 (13) | 0.9234 (10) | 0.201 (8) | 0.50 |
H45 | 0.0141 | 0.4052 | 0.8561 | 0.241* | 0.50 |
H46 | 0.0763 | 0.3655 | 0.9368 | 0.241* | 0.50 |
C2E | 0.1751 (14) | 0.5317 (11) | 0.9656 (11) | 0.149 (5) | 0.50 |
H47 | 0.2201 | 0.5455 | 0.9188 | 0.179* | 0.50 |
H48 | 0.2459 | 0.5279 | 1.0164 | 0.179* | 0.50 |
H49 | 0.1443 | 0.5912 | 0.9884 | 0.179* | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0483 (2) | 0.0620 (2) | 0.0543 (2) | 0.02772 (15) | 0.01953 (14) | 0.02128 (15) |
S15 | 0.0489 (4) | 0.0642 (4) | 0.0628 (4) | 0.0212 (3) | 0.0216 (3) | 0.0200 (3) |
S16 | 0.0527 (4) | 0.0670 (4) | 0.0699 (4) | 0.0196 (3) | 0.0293 (3) | 0.0161 (3) |
S17 | 0.0621 (5) | 0.1042 (7) | 0.0738 (5) | 0.0125 (4) | 0.0069 (4) | 0.0378 (5) |
S18 | 0.0778 (5) | 0.0815 (5) | 0.0731 (5) | 0.0397 (4) | 0.0006 (4) | 0.0183 (4) |
N1 | 0.0643 (13) | 0.0688 (12) | 0.0545 (12) | 0.0328 (11) | 0.0251 (10) | 0.0265 (10) |
N14 | 0.0406 (10) | 0.0582 (11) | 0.0550 (11) | 0.0206 (8) | 0.0129 (8) | 0.0163 (9) |
C2 | 0.0770 (19) | 0.0779 (18) | 0.0691 (17) | 0.0324 (16) | 0.0289 (15) | 0.0293 (14) |
C3 | 0.094 (3) | 0.098 (2) | 0.086 (2) | 0.037 (2) | 0.042 (2) | 0.037 (2) |
C4 | 0.078 (2) | 0.096 (2) | 0.086 (2) | 0.0365 (18) | 0.0429 (18) | 0.0331 (19) |
C5 | 0.0600 (17) | 0.0841 (18) | 0.0604 (15) | 0.0341 (15) | 0.0230 (13) | 0.0156 (14) |
C6 | 0.0568 (15) | 0.0697 (15) | 0.0514 (13) | 0.0312 (13) | 0.0192 (11) | 0.0172 (11) |
C7 | 0.0708 (19) | 0.086 (2) | 0.0776 (19) | 0.0431 (17) | 0.0235 (16) | 0.0192 (16) |
C8 | 0.0648 (17) | 0.0753 (18) | 0.0726 (18) | 0.0390 (15) | 0.0194 (14) | 0.0236 (15) |
C9 | 0.0518 (14) | 0.0559 (13) | 0.0580 (14) | 0.0236 (11) | 0.0122 (11) | 0.0140 (11) |
C10 | 0.0453 (12) | 0.0563 (13) | 0.0492 (12) | 0.0227 (10) | 0.0110 (10) | 0.0157 (10) |
C11 | 0.0614 (16) | 0.0635 (15) | 0.0694 (16) | 0.0271 (13) | 0.0137 (13) | 0.0244 (13) |
C12 | 0.0620 (17) | 0.0665 (15) | 0.0670 (17) | 0.0213 (13) | 0.0166 (13) | 0.0279 (13) |
C13 | 0.0508 (13) | 0.0604 (13) | 0.0637 (15) | 0.0186 (11) | 0.0175 (11) | 0.0234 (12) |
C19 | 0.0545 (14) | 0.0579 (14) | 0.0604 (14) | 0.0230 (11) | 0.0191 (11) | 0.0184 (11) |
C21 | 0.0548 (15) | 0.0828 (18) | 0.0632 (16) | 0.0337 (14) | 0.0187 (13) | 0.0166 (14) |
N20 | 0.0755 (17) | 0.0807 (17) | 0.0646 (15) | 0.0183 (14) | 0.0287 (13) | 0.0040 (13) |
C23 | 0.080 (2) | 0.095 (2) | 0.079 (2) | 0.0287 (19) | 0.0207 (18) | 0.0132 (19) |
C24 | 0.109 (3) | 0.095 (3) | 0.107 (3) | 0.030 (2) | 0.035 (3) | 0.031 (2) |
C25 | 0.111 (4) | 0.130 (4) | 0.125 (4) | 0.027 (3) | 0.019 (3) | 0.038 (3) |
C26 | 0.107 (3) | 0.123 (4) | 0.110 (3) | 0.047 (3) | 0.018 (3) | 0.030 (3) |
C27 | 0.104 (3) | 0.107 (3) | 0.093 (3) | 0.037 (3) | 0.030 (2) | 0.022 (2) |
C28 | 0.106 (4) | 0.139 (4) | 0.130 (4) | 0.055 (3) | 0.023 (3) | 0.048 (4) |
C29 | 0.132 (5) | 0.183 (6) | 0.113 (4) | 0.035 (4) | 0.064 (4) | 0.035 (4) |
C30 | 0.107 (4) | 0.137 (4) | 0.113 (4) | 0.060 (3) | 0.028 (3) | 0.015 (3) |
N22 | 0.0658 (17) | 0.108 (2) | 0.0743 (18) | 0.0231 (16) | −0.0159 (14) | 0.0265 (16) |
C31 | 0.102 (3) | 0.147 (4) | 0.099 (3) | 0.060 (3) | 0.018 (3) | 0.025 (3) |
C32 | 0.114 (4) | 0.150 (5) | 0.145 (5) | 0.077 (4) | 0.059 (4) | 0.064 (4) |
C33 | 0.130 (4) | 0.131 (4) | 0.123 (4) | 0.056 (4) | 0.031 (3) | 0.050 (3) |
C34 | 0.137 (5) | 0.127 (4) | 0.123 (4) | 0.054 (4) | 0.040 (4) | 0.031 (3) |
C35 | 0.135 (5) | 0.165 (6) | 0.130 (5) | 0.058 (5) | 0.033 (4) | 0.052 (4) |
C36 | 0.208 (9) | 0.196 (8) | 0.185 (8) | 0.113 (8) | 0.114 (7) | 0.070 (7) |
C37 | 0.130 (5) | 0.227 (9) | 0.136 (6) | 0.021 (6) | 0.029 (5) | 0.021 (6) |
C38 | 0.182 (8) | 0.190 (8) | 0.168 (7) | 0.063 (7) | 0.037 (6) | 0.076 (6) |
O1E | 0.164 (7) | 0.087 (4) | 0.100 (4) | 0.046 (4) | 0.012 (4) | 0.044 (3) |
C1E | 0.26 (2) | 0.27 (2) | 0.155 (13) | 0.15 (2) | 0.071 (15) | 0.141 (16) |
C2E | 0.112 (8) | 0.167 (11) | 0.209 (14) | 0.056 (8) | 0.048 (9) | 0.136 (12) |
Zn—N14 | 2.178 (2) | C26—H16 | 0.9600 |
Zn—N1 | 2.284 (2) | C26—H17 | 0.9600 |
Zn—S17 | 2.4605 (10) | C27—C28 | 1.498 (7) |
Zn—S15 | 2.4793 (11) | C27—H18 | 0.9700 |
Zn—S16 | 2.5083 (9) | C27—H19 | 0.9700 |
Zn—S18 | 2.6012 (14) | C28—C29 | 1.497 (8) |
S15—C19 | 1.714 (3) | C28—H20 | 0.9700 |
S16—C19 | 1.726 (3) | C28—H21 | 0.9700 |
S17—C21 | 1.688 (3) | C29—C30 | 1.502 (8) |
S18—C21 | 1.691 (4) | C29—H22 | 0.9700 |
N1—C6 | 1.338 (4) | C29—H23 | 0.9700 |
N1—C2 | 1.338 (4) | C30—H24 | 0.9600 |
N14—C13 | 1.309 (3) | C30—H25 | 0.9600 |
N14—C10 | 1.363 (3) | C30—H26 | 0.9600 |
C2—C3 | 1.388 (5) | N22—C31 | 1.433 (6) |
C2—H1 | 0.9300 | N22—C35 | 1.486 (8) |
C3—C4 | 1.374 (6) | C31—C32 | 1.509 (7) |
C3—H2 | 0.9300 | C31—H27 | 0.9700 |
C4—C5 | 1.403 (5) | C31—H28 | 0.9700 |
C4—H3 | 0.9300 | C32—C33 | 1.553 (7) |
C5—C6 | 1.393 (4) | C32—H29 | 0.9700 |
C5—C7 | 1.434 (5) | C32—H30 | 0.9700 |
C6—C10 | 1.438 (4) | C33—C34 | 1.485 (8) |
C7—C8 | 1.332 (5) | C33—H31 | 0.9700 |
C7—H4 | 0.9300 | C33—H32 | 0.9700 |
C8—C9 | 1.417 (4) | C34—H33 | 0.9600 |
C8—H5 | 0.9300 | C34—H34 | 0.9600 |
C9—C10 | 1.395 (4) | C34—H35 | 0.9600 |
C9—C11 | 1.409 (4) | C35—C36 | 1.454 (10) |
C11—C12 | 1.377 (5) | C35—H36 | 0.9700 |
C11—H6 | 0.9300 | C35—H37 | 0.9700 |
C12—C13 | 1.408 (4) | C36—C37 | 1.572 (11) |
C12—H7 | 0.9300 | C36—H38 | 0.9700 |
C13—H8 | 0.9300 | C36—H39 | 0.9700 |
C19—N20 | 1.320 (4) | C37—C38 | 1.465 (11) |
C21—N22 | 1.344 (4) | C37—H40 | 0.9700 |
N20—C23 | 1.451 (5) | C37—H41 | 0.9700 |
N20—C27 | 1.500 (6) | C38—H42 | 0.9600 |
C23—C24 | 1.526 (7) | C38—H43 | 0.9600 |
C23—H9 | 0.9700 | C38—H44 | 0.9600 |
C23—H10 | 0.9700 | O1E—C1E | 1.441 (9) |
C24—C25 | 1.516 (7) | C1E—C2E | 1.509 (9) |
C24—H11 | 0.9700 | C1E—H45 | 0.9700 |
C24—H12 | 0.9700 | C1E—H46 | 0.9700 |
C25—C26 | 1.480 (7) | C2E—H47 | 0.9600 |
C25—H13 | 0.9700 | C2E—H48 | 0.9600 |
C25—H14 | 0.9700 | C2E—H49 | 0.9600 |
C26—H15 | 0.9600 | ||
N14—Zn—N1 | 73.48 (8) | C25—C26—H17 | 109.5 |
N14—Zn—S17 | 148.09 (6) | H15—C26—H17 | 109.5 |
N1—Zn—S17 | 93.51 (7) | H16—C26—H17 | 109.5 |
N14—Zn—S15 | 104.44 (6) | C28—C27—N20 | 109.2 (4) |
N1—Zn—S15 | 85.01 (7) | C28—C27—H18 | 109.8 |
S17—Zn—S15 | 103.22 (4) | N20—C27—H18 | 109.8 |
N14—Zn—S16 | 96.42 (6) | C28—C27—H19 | 109.8 |
N1—Zn—S16 | 151.84 (6) | N20—C27—H19 | 109.8 |
S17—Zn—S16 | 107.07 (4) | H18—C27—H19 | 108.3 |
S15—Zn—S16 | 71.92 (3) | C27—C28—C29 | 109.2 (5) |
N14—Zn—S18 | 86.24 (6) | C27—C28—H20 | 109.8 |
N1—Zn—S18 | 107.91 (7) | C29—C28—H20 | 109.9 |
S17—Zn—S18 | 69.90 (4) | C27—C28—H21 | 109.8 |
S15—Zn—S18 | 165.37 (3) | C29—C28—H21 | 109.8 |
S16—Zn—S18 | 97.29 (4) | H20—C28—H21 | 108.3 |
C19—S15—Zn | 86.25 (10) | C30—C29—C28 | 107.2 (5) |
C19—S16—Zn | 85.09 (10) | C30—C29—H22 | 110.3 |
C21—S17—Zn | 88.08 (12) | C28—C29—H22 | 110.3 |
C21—S18—Zn | 83.48 (11) | C30—C29—H23 | 110.3 |
C6—N1—C2 | 117.2 (3) | C28—C29—H23 | 110.3 |
C6—N1—Zn | 114.81 (18) | H22—C29—H23 | 108.5 |
C2—N1—Zn | 127.6 (2) | C29—C30—H24 | 109.5 |
C13—N14—C10 | 118.8 (2) | C29—C30—H25 | 109.5 |
C13—N14—Zn | 123.92 (19) | H24—C30—H25 | 109.5 |
C10—N14—Zn | 117.23 (17) | C29—C30—H26 | 109.5 |
N1—C2—C3 | 122.3 (3) | H24—C30—H26 | 109.5 |
N1—C2—H1 | 118.8 | H25—C30—H26 | 109.5 |
C3—C2—H1 | 118.8 | C21—N22—C31 | 121.7 (4) |
C4—C3—C2 | 120.4 (3) | C21—N22—C35 | 119.1 (4) |
C4—C3—H2 | 119.8 | C31—N22—C35 | 112.1 (4) |
C2—C3—H2 | 119.8 | N22—C31—C32 | 108.4 (5) |
C3—C4—C5 | 118.2 (3) | N22—C31—H27 | 110.0 |
C3—C4—H3 | 120.9 | C32—C31—H27 | 110.0 |
C5—C4—H3 | 120.9 | N22—C31—H28 | 110.0 |
C6—C5—C4 | 117.4 (3) | C32—C31—H28 | 110.0 |
C6—C5—C7 | 119.0 (3) | H27—C31—H28 | 108.4 |
C4—C5—C7 | 123.6 (3) | C31—C32—C33 | 106.6 (5) |
N1—C6—C5 | 124.5 (3) | C31—C32—H29 | 110.4 |
N1—C6—C10 | 116.7 (2) | C33—C32—H29 | 110.4 |
C5—C6—C10 | 118.8 (3) | C31—C32—H30 | 110.4 |
C8—C7—C5 | 122.1 (3) | C33—C32—H30 | 110.4 |
C8—C7—H4 | 119.0 | H29—C32—H30 | 108.6 |
C5—C7—H4 | 119.0 | C34—C33—C32 | 108.4 (5) |
C7—C8—C9 | 120.2 (3) | C34—C33—H31 | 110.0 |
C7—C8—H5 | 119.9 | C32—C33—H31 | 110.0 |
C9—C8—H5 | 119.9 | C34—C33—H32 | 110.0 |
C10—C9—C11 | 117.1 (3) | C32—C33—H32 | 110.0 |
C10—C9—C8 | 119.8 (3) | H31—C33—H32 | 108.4 |
C11—C9—C8 | 123.1 (3) | C33—C34—H33 | 109.5 |
N14—C10—C9 | 122.5 (2) | C33—C34—H34 | 109.5 |
N14—C10—C6 | 117.5 (2) | H33—C34—H34 | 109.5 |
C9—C10—C6 | 120.0 (2) | C33—C34—H35 | 109.5 |
C12—C11—C9 | 120.5 (3) | H33—C34—H35 | 109.5 |
C12—C11—H6 | 119.7 | H34—C34—H35 | 109.5 |
C9—C11—H6 | 119.7 | C36—C35—N22 | 106.6 (7) |
C11—C12—C13 | 117.5 (3) | C36—C35—H36 | 110.4 |
C11—C12—H7 | 121.3 | N22—C35—H36 | 110.4 |
C13—C12—H7 | 121.3 | C36—C35—H37 | 110.4 |
N14—C13—C12 | 123.5 (3) | N22—C35—H37 | 110.4 |
N14—C13—H8 | 118.2 | H36—C35—H37 | 108.6 |
C12—C13—H8 | 118.2 | C35—C36—C37 | 105.5 (6) |
N20—C19—S15 | 122.0 (2) | C35—C36—H38 | 110.6 |
N20—C19—S16 | 121.3 (2) | C37—C36—H38 | 110.6 |
S15—C19—S16 | 116.73 (16) | C35—C36—H39 | 110.6 |
N22—C21—S18 | 121.3 (3) | C37—C36—H39 | 110.6 |
N22—C21—S17 | 120.2 (3) | H38—C36—H39 | 108.8 |
S18—C21—S17 | 118.38 (18) | C38—C37—C36 | 108.6 (7) |
C19—N20—C23 | 120.6 (3) | C38—C37—H40 | 110.0 |
C19—N20—C27 | 122.0 (3) | C36—C37—H40 | 110.0 |
C23—N20—C27 | 115.1 (3) | C38—C37—H41 | 110.0 |
N20—C23—C24 | 109.3 (4) | C36—C37—H41 | 110.0 |
N20—C23—H9 | 109.8 | H40—C37—H41 | 108.4 |
C24—C23—H9 | 109.8 | C37—C38—H42 | 109.5 |
N20—C23—H10 | 109.8 | C37—C38—H43 | 109.5 |
C24—C23—H10 | 109.8 | H42—C38—H43 | 109.5 |
H9—C23—H10 | 108.3 | C37—C38—H44 | 109.5 |
C25—C24—C23 | 109.4 (4) | H42—C38—H44 | 109.5 |
C25—C24—H11 | 109.8 | H43—C38—H44 | 109.5 |
C23—C24—H11 | 109.8 | O1E—C1E—C2E | 123.5 (13) |
C25—C24—H12 | 109.8 | O1E—C1E—H45 | 106.4 |
C23—C24—H12 | 109.8 | C2E—C1E—H45 | 106.5 |
H11—C24—H12 | 108.2 | O1E—C1E—H46 | 106.4 |
C24—C25—C26 | 109.0 (5) | C2E—C1E—H46 | 106.4 |
C24—C25—H13 | 109.9 | H45—C1E—H46 | 106.5 |
C26—C25—H13 | 109.9 | C1E—C2E—H47 | 109.4 |
C24—C25—H14 | 109.9 | C1E—C2E—H48 | 109.5 |
C26—C25—H14 | 109.9 | H47—C2E—H48 | 109.5 |
H13—C25—H14 | 108.3 | C1E—C2E—H49 | 109.5 |
C25—C26—H15 | 109.5 | H47—C2E—H49 | 109.5 |
C25—C26—H16 | 109.5 | H48—C2E—H49 | 109.5 |
H15—C26—H16 | 109.5 |
[Ca(C13H26NS2)2(C12H8N2)2] | Z = 2 |
Mr = 921.42 | F(000) = 988 |
Triclinic, P1 | Dx = 1.191 Mg m−3 |
a = 11.875 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.129 (2) Å | Cell parameters from 25 reflections |
c = 17.547 (4) Å | θ = 12–20° |
α = 72.29 (1)° | µ = 0.32 mm−1 |
β = 80.91 (2)° | T = 293 K |
γ = 84.20 (2)° | Prismatic, yellow |
V = 2569.2 (11) Å3 | 0.30 × 0.28 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.6° |
Graphite monochromator | h = −13→14 |
2θ/ω scans | k = −14→15 |
9086 measured reflections | l = 0→20 |
9086 independent reflections | 3 standard reflections every 120 min |
7339 reflections with I > 2σ(I) | intensity decay: 0.4% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1184P)2] where P = (Fo2 + 2Fc2)/3 |
9086 reflections | (Δ/σ)max = 0.010 |
550 parameters | Δρmax = 0.82 e Å−3 |
316 restraints | Δρmin = −0.24 e Å−3 |
[Ca(C13H26NS2)2(C12H8N2)2] | γ = 84.20 (2)° |
Mr = 921.42 | V = 2569.2 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 11.875 (4) Å | Mo Kα radiation |
b = 13.129 (2) Å | µ = 0.32 mm−1 |
c = 17.547 (4) Å | T = 293 K |
α = 72.29 (1)° | 0.30 × 0.28 × 0.25 mm |
β = 80.91 (2)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.000 |
9086 measured reflections | 3 standard reflections every 120 min |
9086 independent reflections | intensity decay: 0.4% |
7339 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.042 | 316 restraints |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.82 e Å−3 |
9086 reflections | Δρmin = −0.24 e Å−3 |
550 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. |
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. |
x | y | z | Uiso*/Ueq | ||
Ca | 0.73286 (3) | 0.23019 (3) | 0.05432 (2) | 0.04401 (13) | |
S29 | 0.50466 (4) | 0.29536 (5) | 0.11549 (3) | 0.05741 (16) | |
S30 | 0.69420 (4) | 0.31815 (4) | 0.19825 (3) | 0.05478 (15) | |
S31 | 0.93539 (5) | 0.12354 (5) | 0.12471 (4) | 0.06423 (17) | |
S32 | 0.71069 (5) | 0.04059 (4) | 0.20207 (4) | 0.06023 (16) | |
N1 | 0.90333 (15) | 0.26229 (13) | −0.06464 (10) | 0.0517 (4) | |
N14 | 0.78812 (14) | 0.42403 (11) | −0.01259 (9) | 0.0461 (3) | |
N15 | 0.60723 (14) | 0.27956 (12) | −0.06285 (9) | 0.0462 (3) | |
N28 | 0.70927 (15) | 0.08110 (12) | −0.00674 (10) | 0.0512 (4) | |
N34 | 0.47861 (15) | 0.29887 (16) | 0.26815 (11) | 0.0591 (4) | |
N36 | 0.88987 (17) | 0.01289 (15) | 0.27953 (12) | 0.0637 (5) | |
C2 | 0.9597 (2) | 0.18568 (18) | −0.09347 (14) | 0.0633 (5) | |
H1 | 0.9298 | 0.1184 | −0.0769 | 0.082* | |
C3 | 1.0607 (2) | 0.2009 (2) | −0.14696 (14) | 0.0696 (6) | |
H2 | 1.0968 | 0.1449 | −0.1653 | 0.090* | |
C4 | 1.1063 (2) | 0.2998 (2) | −0.17234 (16) | 0.0717 (6) | |
H3 | 1.1739 | 0.3109 | −0.2079 | 0.093* | |
C5 | 1.05085 (17) | 0.38374 (18) | −0.14463 (12) | 0.0564 (5) | |
C6 | 0.94879 (15) | 0.36132 (14) | −0.09126 (10) | 0.0442 (4) | |
C7 | 1.0919 (2) | 0.4865 (2) | −0.16690 (18) | 0.0744 (7) | |
H4 | 1.1607 | 0.5003 | −0.2008 | 0.097* | |
C8 | 1.0356 (2) | 0.56406 (19) | −0.14105 (17) | 0.0683 (6) | |
H5 | 1.0663 | 0.6309 | −0.1568 | 0.089* | |
C9 | 0.92998 (17) | 0.54865 (15) | −0.09009 (12) | 0.0509 (4) | |
C10 | 0.88602 (15) | 0.44651 (14) | −0.06285 (10) | 0.0422 (4) | |
C11 | 0.8643 (2) | 0.62967 (15) | −0.06317 (15) | 0.0608 (5) | |
H6 | 0.8905 | 0.6983 | −0.0783 | 0.079* | |
C12 | 0.7637 (2) | 0.60804 (16) | −0.01562 (15) | 0.0608 (5) | |
H7 | 0.7185 | 0.6621 | 0.0002 | 0.079* | |
C13 | 0.72849 (19) | 0.50404 (15) | 0.00937 (13) | 0.0535 (4) | |
H8 | 0.6597 | 0.4897 | 0.0432 | 0.070* | |
C16 | 0.55512 (19) | 0.37433 (16) | −0.09103 (13) | 0.0555 (5) | |
H9 | 0.5697 | 0.4289 | −0.0710 | 0.072* | |
C17 | 0.4804 (2) | 0.39904 (18) | −0.14813 (14) | 0.0627 (5) | |
H10 | 0.4495 | 0.4685 | −0.1676 | 0.081* | |
C18 | 0.4536 (2) | 0.3185 (2) | −0.17478 (15) | 0.0665 (6) | |
H11 | 0.4015 | 0.3319 | −0.2115 | 0.087* | |
C19 | 0.50478 (17) | 0.21478 (17) | −0.14679 (13) | 0.0552 (5) | |
C20 | 0.58112 (15) | 0.19931 (15) | −0.09177 (11) | 0.0444 (4) | |
C21 | 0.4806 (2) | 0.1273 (2) | −0.17275 (18) | 0.0761 (7) | |
H12 | 0.4281 | 0.1376 | −0.2088 | 0.099* | |
C22 | 0.5332 (2) | 0.0302 (2) | −0.14550 (18) | 0.0744 (7) | |
H13 | 0.5169 | −0.0259 | −0.1633 | 0.097* | |
C23 | 0.61351 (17) | 0.01208 (17) | −0.08983 (14) | 0.0558 (5) | |
C24 | 0.63692 (15) | 0.09372 (14) | −0.06111 (12) | 0.0470 (4) | |
C25 | 0.6731 (2) | −0.08884 (16) | −0.06137 (15) | 0.0657 (6) | |
H14 | 0.6601 | −0.1462 | −0.0789 | 0.085* | |
C26 | 0.7472 (2) | −0.10075 (17) | −0.00991 (17) | 0.0695 (6) | |
H15 | 0.7889 | −0.1655 | 0.0071 | 0.090* | |
C27 | 0.7623 (2) | −0.01502 (16) | 0.01875 (15) | 0.0648 (6) | |
H16 | 0.8115 | −0.0257 | 0.0572 | 0.084* | |
C33 | 0.55384 (16) | 0.30300 (14) | 0.20069 (11) | 0.0466 (4) | |
C35 | 0.84855 (17) | 0.05518 (14) | 0.20921 (13) | 0.0503 (4) | |
C37 | 0.3559 (2) | 0.2883 (2) | 0.27189 (14) | 0.0731 (7) | |
H17 | 0.3256 | 0.2515 | 0.3271 | 0.095* | |
H18 | 0.3457 | 0.2437 | 0.2386 | 0.095* | |
C38 | 0.2882 (2) | 0.3911 (3) | 0.24500 (17) | 0.0814 (8) | |
H19 | 0.3185 | 0.4275 | 0.1897 | 0.106* | |
H20 | 0.2102 | 0.3753 | 0.2450 | 0.106* | |
C39 | 0.2863 (3) | 0.4654 (3) | 0.29387 (18) | 0.0880 (8) | |
H21 | 0.3642 | 0.4824 | 0.2928 | 0.114* | |
H22 | 0.2577 | 0.4284 | 0.3494 | 0.114* | |
C40 | 0.2170 (3) | 0.5669 (3) | 0.2685 (2) | 0.1050 (11) | |
H23 | 0.2427 | 0.6026 | 0.2122 | 0.136* | |
H24 | 0.1380 | 0.5505 | 0.2725 | 0.136* | |
C41 | 0.2223 (5) | 0.6395 (4) | 0.3152 (3) | 0.151 (2) | |
H25 | 0.3017 | 0.6535 | 0.3124 | 0.196* | |
H26 | 0.1949 | 0.6037 | 0.3712 | 0.196* | |
C42 | 0.1576 (6) | 0.7420 (5) | 0.2908 (4) | 0.168 (2) | |
H27 | 0.1092 | 0.7400 | 0.2524 | 0.219* | |
H28 | 0.2095 | 0.7981 | 0.2666 | 0.219* | |
H29 | 0.1115 | 0.7552 | 0.3373 | 0.219* | |
C43 | 0.5179 (2) | 0.2982 (2) | 0.34229 (14) | 0.0729 (6) | |
H30 | 0.4565 | 0.3281 | 0.3739 | 0.095* | |
H31 | 0.5809 | 0.3449 | 0.3288 | 0.095* | |
C44 | 0.5556 (3) | 0.1922 (3) | 0.39282 (16) | 0.0920 (9) | |
H32 | 0.4908 | 0.1473 | 0.4095 | 0.120* | |
H | 0.6126 | 0.1601 | 0.3597 | 0.120* | |
C45 | 0.6036 (4) | 0.1906 (4) | 0.4653 (2) | 0.1132 (12) | |
H33 | 0.6753 | 0.2257 | 0.4477 | 0.147* | |
H34 | 0.5522 | 0.2341 | 0.4930 | 0.147* | |
C46 | 0.6252 (5) | 0.0883 (4) | 0.5237 (2) | 0.1293 (15) | |
H35 | 0.6820 | 0.0464 | 0.4980 | 0.168* | |
H36 | 0.5554 | 0.0503 | 0.5393 | 0.168* | |
C47 | 0.6663 (6) | 0.0956 (5) | 0.5991 (3) | 0.156 (2) | |
H37 | 0.7418 | 0.1235 | 0.5843 | 0.203* | |
H38 | 0.6159 | 0.1469 | 0.6197 | 0.203* | |
C48 | 0.6718 (6) | −0.0061 (6) | 0.6647 (4) | 0.183 (3) | |
H39 | 0.6302 | −0.0582 | 0.6540 | 0.238* | |
H40 | 0.6387 | 0.0056 | 0.7151 | 0.238* | |
H41 | 0.7501 | −0.0318 | 0.6675 | 0.238* | |
C49 | 1.0085 (3) | 0.0226 (3) | 0.2883 (2) | 0.0908 (9) | |
H42 | 1.0571 | 0.0115 | 0.2413 | 0.118* | |
H43 | 1.0285 | −0.0345 | 0.3350 | 0.118* | |
C50 | 1.0347 (4) | 0.1262 (4) | 0.2977 (3) | 0.1369 (17) | |
H44 | 1.1162 | 0.1251 | 0.2990 | 0.178* | |
H45 | 1.0168 | 0.1830 | 0.2502 | 0.178* | |
C51 | 0.9753 (4) | 0.1525 (5) | 0.3685 (4) | 0.150 (2) | |
H46 | 0.9863 | 0.0926 | 0.4158 | 0.194* | |
H47 | 0.8942 | 0.1621 | 0.3644 | 0.194* | |
C52 | 1.0129 (5) | 0.2498 (5) | 0.3800 (4) | 0.167 (2) | |
H48 | 1.0088 | 0.3077 | 0.3304 | 0.217* | |
H49 | 1.0924 | 0.2373 | 0.3887 | 0.217* | |
C53 | 0.9476 (7) | 0.2855 (6) | 0.4475 (5) | 0.200 (3) | |
H50 | 0.8672 | 0.2908 | 0.4417 | 0.260* | |
H51 | 0.9579 | 0.2301 | 0.4975 | 0.260* | |
C54 | 0.9764 (6) | 0.3873 (6) | 0.4555 (5) | 0.182 (3) | |
H52 | 0.9285 | 0.4445 | 0.4262 | 0.237* | |
H53 | 1.0550 | 0.3996 | 0.4341 | 0.237* | |
H54 | 0.9644 | 0.3846 | 0.5115 | 0.237* | |
C55 | 0.8190 (2) | −0.0495 (2) | 0.35136 (16) | 0.0744 (6) | |
H55 | 0.7422 | −0.0163 | 0.3520 | 0.097* | |
H56 | 0.8484 | −0.0448 | 0.3987 | 0.097* | |
C56 | 0.8118 (3) | −0.1653 (2) | 0.35882 (19) | 0.0838 (8) | |
H57 | 0.7851 | −0.1710 | 0.3109 | 0.109* | |
H58 | 0.8877 | −0.2002 | 0.3613 | 0.109* | |
C57 | 0.7348 (4) | −0.2221 (3) | 0.4307 (3) | 0.1170 (13) | |
H59 | 0.6589 | −0.1873 | 0.4277 | 0.152* | |
H60 | 0.7611 | −0.2154 | 0.4784 | 0.152* | |
C58 | 0.7267 (6) | −0.3398 (4) | 0.4403 (4) | 0.169 (2) | |
H61 | 0.8028 | −0.3703 | 0.4279 | 0.220* | |
H62 | 0.6996 | −0.3756 | 0.4963 | 0.220* | |
C59 | 0.6518 (7) | −0.3626 (5) | 0.3896 (4) | 0.175 (2) | |
H63 | 0.5769 | −0.3287 | 0.3999 | 0.228* | |
H64 | 0.6813 | −0.3296 | 0.3335 | 0.228* | |
C60 | 0.6385 (8) | −0.4751 (6) | 0.4007 (6) | 0.225 (4) | |
H65 | 0.5784 | −0.4818 | 0.3720 | 0.292* | |
H66 | 0.6195 | −0.5112 | 0.4571 | 0.292* | |
H67 | 0.7086 | −0.5067 | 0.3802 | 0.292* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ca | 0.0501 (2) | 0.0284 (2) | 0.0577 (2) | −0.00478 (15) | −0.00767 (16) | −0.01777 (15) |
S29 | 0.0526 (3) | 0.0636 (3) | 0.0642 (3) | −0.0032 (2) | −0.0098 (2) | −0.0299 (2) |
S30 | 0.0498 (3) | 0.0533 (3) | 0.0684 (3) | −0.0107 (2) | −0.0058 (2) | −0.0269 (2) |
S31 | 0.0555 (3) | 0.0541 (3) | 0.0803 (4) | −0.0085 (2) | −0.0103 (3) | −0.0134 (3) |
S32 | 0.0577 (3) | 0.0474 (3) | 0.0761 (3) | −0.0151 (2) | −0.0166 (2) | −0.0112 (2) |
N1 | 0.0564 (9) | 0.0393 (8) | 0.0612 (9) | 0.0033 (7) | −0.0055 (7) | −0.0203 (7) |
N14 | 0.0545 (9) | 0.0311 (7) | 0.0552 (8) | −0.0074 (6) | −0.0007 (7) | −0.0182 (6) |
N15 | 0.0538 (8) | 0.0350 (7) | 0.0543 (8) | −0.0019 (6) | −0.0069 (6) | −0.0201 (6) |
N28 | 0.0611 (9) | 0.0323 (7) | 0.0647 (9) | −0.0047 (7) | −0.0130 (7) | −0.0181 (7) |
N34 | 0.0510 (9) | 0.0703 (12) | 0.0577 (9) | −0.0130 (8) | −0.0026 (7) | −0.0207 (8) |
N36 | 0.0679 (11) | 0.0513 (10) | 0.0752 (11) | −0.0031 (8) | −0.0245 (9) | −0.0157 (8) |
C2 | 0.0767 (14) | 0.0467 (11) | 0.0687 (12) | 0.0046 (10) | −0.0060 (10) | −0.0246 (9) |
C3 | 0.0694 (14) | 0.0686 (15) | 0.0670 (13) | 0.0199 (12) | 0.0028 (11) | −0.0279 (11) |
C4 | 0.0542 (12) | 0.0785 (16) | 0.0750 (14) | 0.0066 (11) | 0.0060 (10) | −0.0225 (12) |
C5 | 0.0446 (10) | 0.0638 (13) | 0.0589 (10) | −0.0006 (9) | −0.0074 (8) | −0.0155 (9) |
C6 | 0.0451 (9) | 0.0400 (9) | 0.0468 (8) | −0.0019 (7) | −0.0104 (7) | −0.0097 (7) |
C7 | 0.0468 (11) | 0.0845 (17) | 0.0903 (16) | −0.0200 (11) | 0.0052 (11) | −0.0253 (13) |
C8 | 0.0608 (13) | 0.0535 (12) | 0.0901 (16) | −0.0185 (10) | −0.0130 (11) | −0.0141 (11) |
C9 | 0.0514 (10) | 0.0411 (9) | 0.0645 (11) | −0.0157 (8) | −0.0170 (8) | −0.0128 (8) |
C10 | 0.0440 (9) | 0.0368 (9) | 0.0480 (8) | −0.0074 (7) | −0.0124 (7) | −0.0110 (7) |
C11 | 0.0704 (13) | 0.0313 (9) | 0.0853 (14) | −0.0126 (9) | −0.0204 (11) | −0.0160 (9) |
C12 | 0.0703 (13) | 0.0363 (9) | 0.0823 (13) | −0.0029 (9) | −0.0114 (11) | −0.0266 (9) |
C13 | 0.0629 (11) | 0.0364 (9) | 0.0656 (11) | −0.0053 (8) | −0.0062 (9) | −0.0218 (8) |
C16 | 0.0662 (12) | 0.0387 (9) | 0.0640 (11) | 0.0022 (8) | −0.0094 (9) | −0.0196 (8) |
C17 | 0.0628 (12) | 0.0544 (12) | 0.0657 (12) | 0.0110 (10) | −0.0040 (10) | −0.0170 (10) |
C18 | 0.0612 (13) | 0.0705 (14) | 0.0723 (13) | 0.0057 (10) | −0.0234 (10) | −0.0231 (11) |
C19 | 0.0535 (11) | 0.0533 (11) | 0.0666 (11) | −0.0068 (9) | −0.0114 (9) | −0.0260 (9) |
C20 | 0.0393 (8) | 0.0437 (9) | 0.0506 (9) | −0.0075 (7) | 0.0037 (7) | −0.0177 (7) |
C21 | 0.0808 (16) | 0.0733 (16) | 0.0925 (17) | −0.0134 (13) | −0.0347 (14) | −0.0370 (14) |
C22 | 0.0783 (15) | 0.0587 (13) | 0.1031 (18) | −0.0159 (11) | −0.0243 (13) | −0.0389 (13) |
C23 | 0.0544 (11) | 0.0472 (10) | 0.0764 (12) | −0.0145 (8) | −0.0045 (9) | −0.0321 (10) |
C24 | 0.0430 (9) | 0.0372 (9) | 0.0655 (10) | −0.0080 (7) | −0.0021 (8) | −0.0228 (8) |
C25 | 0.0887 (16) | 0.0363 (9) | 0.0799 (14) | −0.0147 (10) | −0.0061 (12) | −0.0275 (9) |
C26 | 0.0818 (15) | 0.0375 (10) | 0.0989 (17) | 0.0010 (10) | −0.0224 (13) | −0.0308 (11) |
C27 | 0.0881 (16) | 0.0311 (10) | 0.0802 (14) | 0.0010 (9) | −0.0246 (12) | −0.0184 (9) |
C33 | 0.0515 (10) | 0.0366 (8) | 0.0536 (9) | −0.0089 (7) | −0.0001 (8) | −0.0177 (7) |
C35 | 0.0552 (10) | 0.0335 (9) | 0.0654 (10) | −0.0056 (7) | −0.0134 (8) | −0.0157 (8) |
C37 | 0.0613 (13) | 0.0969 (18) | 0.0602 (12) | −0.0284 (13) | 0.0090 (10) | −0.0225 (12) |
C38 | 0.0491 (12) | 0.120 (2) | 0.0741 (14) | −0.0007 (13) | −0.0038 (10) | −0.0305 (15) |
C39 | 0.0709 (16) | 0.113 (2) | 0.0771 (16) | 0.0104 (16) | −0.0047 (13) | −0.0311 (16) |
C40 | 0.083 (2) | 0.140 (3) | 0.095 (2) | 0.020 (2) | −0.0008 (16) | −0.054 (2) |
C41 | 0.145 (4) | 0.159 (5) | 0.146 (4) | 0.064 (4) | −0.038 (3) | −0.057 (4) |
C42 | 0.164 (5) | 0.189 (6) | 0.161 (5) | 0.021 (4) | −0.025 (4) | −0.073 (5) |
C43 | 0.0758 (15) | 0.0874 (18) | 0.0594 (12) | −0.0077 (13) | 0.0002 (11) | −0.0308 (12) |
C44 | 0.102 (2) | 0.100 (2) | 0.0656 (15) | −0.0196 (17) | −0.0130 (14) | −0.0080 (14) |
C45 | 0.105 (3) | 0.153 (4) | 0.0779 (19) | −0.017 (2) | −0.0263 (17) | −0.019 (2) |
C46 | 0.156 (4) | 0.127 (3) | 0.100 (3) | −0.007 (3) | −0.042 (3) | −0.012 (2) |
C47 | 0.157 (5) | 0.163 (5) | 0.147 (4) | −0.007 (4) | −0.040 (4) | −0.036 (4) |
C48 | 0.187 (6) | 0.200 (7) | 0.143 (5) | −0.026 (5) | −0.028 (4) | −0.016 (5) |
C49 | 0.0774 (17) | 0.0821 (19) | 0.118 (2) | −0.0008 (14) | −0.0488 (17) | −0.0203 (17) |
C50 | 0.107 (3) | 0.154 (4) | 0.170 (4) | −0.030 (3) | −0.049 (3) | −0.055 (3) |
C51 | 0.126 (4) | 0.156 (5) | 0.198 (6) | −0.044 (3) | −0.010 (4) | −0.092 (4) |
C52 | 0.151 (5) | 0.186 (6) | 0.185 (6) | −0.045 (4) | −0.023 (4) | −0.075 (5) |
C53 | 0.194 (7) | 0.189 (7) | 0.228 (8) | −0.066 (6) | 0.007 (6) | −0.078 (6) |
C54 | 0.180 (6) | 0.191 (7) | 0.204 (7) | −0.046 (5) | 0.002 (5) | −0.103 (6) |
C55 | 0.0829 (17) | 0.0654 (14) | 0.0743 (14) | 0.0057 (12) | −0.0202 (12) | −0.0177 (11) |
C56 | 0.0934 (19) | 0.0608 (14) | 0.0871 (17) | −0.0021 (13) | −0.0027 (14) | −0.0125 (13) |
C57 | 0.134 (3) | 0.092 (2) | 0.112 (3) | −0.033 (2) | 0.005 (2) | −0.012 (2) |
C58 | 0.175 (6) | 0.122 (4) | 0.184 (6) | −0.047 (4) | −0.008 (5) | −0.001 (4) |
C59 | 0.212 (7) | 0.159 (6) | 0.169 (5) | −0.020 (5) | −0.017 (5) | −0.069 (5) |
C60 | 0.258 (9) | 0.196 (8) | 0.254 (10) | −0.057 (7) | −0.019 (8) | −0.110 (7) |
Ca—N28 | 2.5571 (15) | C38—C39 | 1.478 (4) |
Ca—N14 | 2.5616 (15) | C38—H19 | 0.9700 |
Ca—N15 | 2.6145 (18) | C38—H20 | 0.9700 |
Ca—N1 | 2.6333 (19) | C39—C40 | 1.478 (4) |
Ca—S29 | 2.8981 (11) | C39—H21 | 0.9700 |
Ca—S31 | 2.9114 (11) | C39—H22 | 0.9700 |
Ca—S32 | 2.9963 (8) | C40—C41 | 1.445 (6) |
Ca—S30 | 3.0371 (8) | C40—H23 | 0.9700 |
S29—C33 | 1.722 (2) | C40—H24 | 0.9700 |
S30—C33 | 1.691 (2) | C41—C42 | 1.459 (6) |
S31—C35 | 1.721 (2) | C41—H25 | 0.9700 |
S32—C35 | 1.696 (2) | C41—H26 | 0.9700 |
N1—C2 | 1.335 (3) | C42—H27 | 0.9600 |
N1—C6 | 1.376 (2) | C42—H28 | 0.9600 |
N14—C13 | 1.328 (2) | C42—H29 | 0.9600 |
N14—C10 | 1.343 (2) | C43—C44 | 1.473 (4) |
N15—C16 | 1.320 (3) | C43—H30 | 0.9700 |
N15—C20 | 1.380 (2) | C43—H31 | 0.9700 |
N28—C27 | 1.332 (3) | C44—C45 | 1.467 (4) |
N28—C24 | 1.345 (3) | C44—H32 | 0.9700 |
N34—C33 | 1.356 (3) | C44—H | 0.9700 |
N34—C43 | 1.447 (3) | C45—C46 | 1.448 (5) |
N34—C37 | 1.467 (3) | C45—H33 | 0.9700 |
N36—C35 | 1.338 (3) | C45—H34 | 0.9700 |
N36—C49 | 1.463 (3) | C46—C47 | 1.512 (6) |
N36—C55 | 1.464 (3) | C46—H35 | 0.9700 |
C2—C3 | 1.392 (3) | C46—H36 | 0.9700 |
C2—H1 | 0.9300 | C47—C48 | 1.477 (7) |
C3—C4 | 1.376 (4) | C47—H37 | 0.9700 |
C3—H2 | 0.9300 | C47—H38 | 0.9700 |
C4—C5 | 1.401 (3) | C48—H39 | 0.9600 |
C4—H3 | 0.9300 | C48—H40 | 0.9600 |
C5—C7 | 1.400 (4) | C48—H41 | 0.9600 |
C5—C6 | 1.407 (3) | C49—C50 | 1.488 (5) |
C6—C10 | 1.452 (3) | C49—H42 | 0.9700 |
C7—C8 | 1.319 (4) | C49—H43 | 0.9700 |
C7—H4 | 0.9300 | C50—C51 | 1.448 (6) |
C8—C9 | 1.414 (3) | C50—H44 | 0.9700 |
C8—H5 | 0.9300 | C50—H45 | 0.9700 |
C9—C10 | 1.404 (2) | C51—C52 | 1.474 (6) |
C9—C11 | 1.409 (3) | C51—H46 | 0.9700 |
C11—C12 | 1.347 (3) | C51—H47 | 0.9700 |
C11—H6 | 0.9300 | C52—C53 | 1.483 (7) |
C12—C13 | 1.387 (3) | C52—H48 | 0.9700 |
C12—H7 | 0.9300 | C52—H49 | 0.9700 |
C13—H8 | 0.9300 | C53—C54 | 1.464 (7) |
C16—C17 | 1.386 (3) | C53—H50 | 0.9700 |
C16—H9 | 0.9300 | C53—H51 | 0.9700 |
C17—C18 | 1.362 (4) | C54—H52 | 0.9600 |
C17—H10 | 0.9300 | C54—H53 | 0.9600 |
C18—C19 | 1.409 (3) | C54—H54 | 0.9600 |
C18—H11 | 0.9300 | C55—C56 | 1.497 (4) |
C19—C20 | 1.384 (3) | C55—H55 | 0.9700 |
C19—C21 | 1.426 (3) | C55—H56 | 0.9700 |
C20—C24 | 1.457 (3) | C56—C57 | 1.478 (4) |
C21—C22 | 1.344 (4) | C56—H57 | 0.9700 |
C21—H12 | 0.9300 | C56—H58 | 0.9700 |
C22—C23 | 1.424 (4) | C57—C58 | 1.514 (6) |
C22—H13 | 0.9300 | C57—H59 | 0.9700 |
C23—C24 | 1.383 (3) | C57—H60 | 0.9700 |
C23—C25 | 1.423 (3) | C58—C59 | 1.462 (8) |
C25—C26 | 1.323 (4) | C58—H61 | 0.9700 |
C25—H14 | 0.9300 | C58—H62 | 0.9700 |
C26—C27 | 1.402 (3) | C59—C60 | 1.452 (8) |
C26—H15 | 0.9300 | C59—H63 | 0.9700 |
C27—H16 | 0.9300 | C59—H64 | 0.9700 |
C37—C38 | 1.485 (4) | C60—H65 | 0.9600 |
C37—H17 | 0.9700 | C60—H66 | 0.9600 |
C37—H18 | 0.9700 | C60—H67 | 0.9600 |
N28—Ca—N14 | 131.02 (5) | C37—C38—H19 | 108.3 |
N28—Ca—N15 | 63.48 (5) | C39—C38—H20 | 108.3 |
N14—Ca—N15 | 81.55 (5) | C37—C38—H20 | 108.3 |
N28—Ca—N1 | 78.98 (6) | H19—C38—H20 | 107.4 |
N14—Ca—N1 | 63.20 (5) | C38—C39—C40 | 116.0 (3) |
N15—Ca—N1 | 83.56 (6) | C38—C39—H21 | 108.3 |
N28—Ca—S29 | 106.14 (5) | C40—C39—H21 | 108.3 |
N14—Ca—S29 | 92.79 (4) | C38—C39—H22 | 108.3 |
N15—Ca—S29 | 71.63 (4) | C40—C39—H22 | 108.3 |
N1—Ca—S29 | 148.04 (4) | H21—C39—H22 | 107.4 |
N28—Ca—S31 | 93.34 (4) | C41—C40—C39 | 114.2 (3) |
N14—Ca—S31 | 103.74 (5) | C41—C40—H23 | 108.7 |
N15—Ca—S31 | 150.42 (4) | C39—C40—H23 | 108.7 |
N1—Ca—S31 | 73.59 (5) | C41—C40—H24 | 108.7 |
S29—Ca—S31 | 135.86 (3) | C39—C40—H24 | 108.7 |
N28—Ca—S32 | 78.80 (4) | H23—C40—H24 | 107.6 |
N14—Ca—S32 | 148.88 (4) | C40—C41—C42 | 116.1 (5) |
N15—Ca—S32 | 126.42 (4) | C40—C41—H25 | 108.3 |
N1—Ca—S32 | 126.43 (4) | C42—C41—H25 | 108.3 |
S29—Ca—S32 | 85.16 (3) | C40—C41—H26 | 108.3 |
S31—Ca—S32 | 59.85 (3) | C42—C41—H26 | 108.3 |
N28—Ca—S30 | 149.53 (4) | H25—C41—H26 | 107.4 |
N14—Ca—S30 | 78.73 (4) | C41—C42—H27 | 109.5 |
N15—Ca—S30 | 125.70 (4) | C41—C42—H28 | 109.5 |
N1—Ca—S30 | 128.22 (4) | H27—C42—H28 | 109.5 |
S29—Ca—S30 | 59.54 (2) | C41—C42—H29 | 109.5 |
S31—Ca—S30 | 83.69 (3) | H27—C42—H29 | 109.5 |
S32—Ca—S30 | 73.50 (2) | H28—C42—H29 | 109.5 |
C33—S29—Ca | 90.14 (7) | N34—C43—C44 | 115.4 (2) |
C33—S30—Ca | 86.12 (7) | N34—C43—H30 | 108.4 |
C35—S31—Ca | 89.19 (7) | C44—C43—H30 | 108.4 |
C35—S32—Ca | 86.86 (7) | N34—C43—H31 | 108.4 |
C2—N1—C6 | 116.77 (18) | C44—C43—H31 | 108.4 |
C2—N1—Ca | 124.69 (14) | H30—C43—H31 | 107.5 |
C6—N1—Ca | 117.84 (11) | C45—C44—C43 | 116.3 (3) |
C13—N14—C10 | 117.68 (15) | C45—C44—H32 | 108.2 |
C13—N14—Ca | 120.74 (12) | C43—C44—H32 | 108.2 |
C10—N14—Ca | 121.02 (11) | C45—C44—H | 108.2 |
C16—N15—C20 | 116.09 (17) | C43—C44—H | 108.2 |
C16—N15—Ca | 124.61 (13) | H32—C44—H | 107.4 |
C20—N15—Ca | 118.84 (12) | C46—C45—C44 | 118.6 (4) |
C27—N28—C24 | 117.37 (17) | C46—C45—H33 | 107.7 |
C27—N28—Ca | 120.79 (14) | C44—C45—H33 | 107.7 |
C24—N28—Ca | 121.66 (12) | C46—C45—H34 | 107.7 |
C33—N34—C43 | 120.68 (18) | C44—C45—H34 | 107.7 |
C33—N34—C37 | 122.68 (18) | H33—C45—H34 | 107.1 |
C43—N34—C37 | 116.53 (18) | C45—C46—C47 | 114.6 (4) |
C35—N36—C49 | 122.3 (2) | C45—C46—H35 | 108.6 |
C35—N36—C55 | 121.3 (2) | C47—C46—H35 | 108.6 |
C49—N36—C55 | 116.4 (2) | C45—C46—H36 | 108.6 |
N1—C2—C3 | 123.6 (2) | C47—C46—H36 | 108.6 |
N1—C2—H1 | 118.2 | H35—C46—H36 | 107.6 |
C3—C2—H1 | 118.2 | C48—C47—C46 | 115.5 (5) |
C4—C3—C2 | 119.2 (2) | C48—C47—H37 | 108.4 |
C4—C3—H2 | 120.4 | C46—C47—H37 | 108.4 |
C2—C3—H2 | 120.4 | C48—C47—H38 | 108.4 |
C3—C4—C5 | 119.9 (2) | C46—C47—H38 | 108.4 |
C3—C4—H3 | 120.0 | H37—C47—H38 | 107.5 |
C5—C4—H3 | 120.0 | C47—C48—H39 | 109.5 |
C4—C5—C7 | 123.6 (2) | C47—C48—H40 | 109.5 |
C4—C5—C6 | 117.0 (2) | H39—C48—H40 | 109.5 |
C7—C5—C6 | 119.4 (2) | C47—C48—H41 | 109.5 |
N1—C6—C5 | 123.51 (17) | H39—C48—H41 | 109.5 |
N1—C6—C10 | 117.35 (15) | H40—C48—H41 | 109.5 |
C5—C6—C10 | 119.14 (17) | N36—C49—C50 | 115.8 (3) |
C8—C7—C5 | 121.7 (2) | N36—C49—H42 | 108.3 |
C8—C7—H4 | 119.1 | C50—C49—H42 | 108.3 |
C5—C7—H4 | 119.1 | N36—C49—H43 | 108.3 |
C7—C8—C9 | 122.0 (2) | C50—C49—H43 | 108.3 |
C7—C8—H5 | 119.0 | H42—C49—H43 | 107.4 |
C9—C8—H5 | 119.0 | C51—C50—C49 | 116.0 (4) |
C10—C9—C11 | 116.41 (18) | C51—C50—H44 | 108.3 |
C10—C9—C8 | 119.29 (19) | C49—C50—H44 | 108.3 |
C11—C9—C8 | 124.30 (18) | C51—C50—H45 | 108.3 |
N14—C10—C9 | 123.26 (17) | C49—C50—H45 | 108.3 |
N14—C10—C6 | 118.38 (15) | H44—C50—H45 | 107.4 |
C9—C10—C6 | 118.36 (17) | C50—C51—C52 | 114.1 (5) |
C12—C11—C9 | 120.22 (17) | C50—C51—H46 | 108.7 |
C12—C11—H6 | 119.9 | C52—C51—H46 | 108.7 |
C9—C11—H6 | 119.9 | C50—C51—H47 | 108.7 |
C11—C12—C13 | 119.07 (19) | C52—C51—H47 | 108.7 |
C11—C12—H7 | 120.5 | H46—C51—H47 | 107.6 |
C13—C12—H7 | 120.5 | C51—C52—C53 | 116.1 (5) |
N14—C13—C12 | 123.26 (19) | C51—C52—H48 | 108.3 |
N14—C13—H8 | 118.4 | C53—C52—H48 | 108.3 |
C12—C13—H8 | 118.4 | C51—C52—H49 | 108.3 |
N15—C16—C17 | 125.23 (19) | C53—C52—H49 | 108.3 |
N15—C16—H9 | 117.4 | H48—C52—H49 | 107.4 |
C17—C16—H9 | 117.4 | C54—C53—C52 | 117.1 (6) |
C18—C17—C16 | 117.9 (2) | C54—C53—H50 | 108.0 |
C18—C17—H10 | 121.0 | C52—C53—H50 | 108.0 |
C16—C17—H10 | 121.0 | C54—C53—H51 | 108.0 |
C17—C18—C19 | 120.1 (2) | C52—C53—H51 | 108.0 |
C17—C18—H11 | 120.0 | H50—C53—H51 | 107.3 |
C19—C18—H11 | 120.0 | C53—C54—H52 | 109.5 |
C20—C19—C18 | 117.41 (19) | C53—C54—H53 | 109.5 |
C20—C19—C21 | 119.9 (2) | H52—C54—H53 | 109.5 |
C18—C19—C21 | 122.7 (2) | C53—C54—H54 | 109.5 |
N15—C20—C19 | 123.17 (17) | H52—C54—H54 | 109.5 |
N15—C20—C24 | 117.13 (17) | H53—C54—H54 | 109.5 |
C19—C20—C24 | 119.69 (17) | N36—C55—C56 | 116.2 (2) |
C22—C21—C19 | 120.6 (2) | N36—C55—H55 | 108.2 |
C22—C21—H12 | 119.7 | C56—C55—H55 | 108.2 |
C19—C21—H12 | 119.7 | N36—C55—H56 | 108.2 |
C21—C22—C23 | 120.9 (2) | C56—C55—H56 | 108.2 |
C21—C22—H13 | 119.6 | H55—C55—H56 | 107.4 |
C23—C22—H13 | 119.6 | C57—C56—C55 | 113.3 (3) |
C24—C23—C25 | 117.0 (2) | C57—C56—H57 | 108.9 |
C24—C23—C22 | 120.5 (2) | C55—C56—H57 | 108.9 |
C25—C23—C22 | 122.47 (19) | C57—C56—H58 | 108.9 |
N28—C24—C23 | 123.48 (18) | C55—C56—H58 | 108.9 |
N28—C24—C20 | 118.13 (16) | H57—C56—H58 | 107.7 |
C23—C24—C20 | 118.40 (19) | C56—C57—C58 | 114.5 (4) |
C26—C25—C23 | 119.76 (18) | C56—C57—H59 | 108.6 |
C26—C25—H14 | 120.1 | C58—C57—H59 | 108.6 |
C23—C25—H14 | 120.1 | C56—C57—H60 | 108.6 |
C25—C26—C27 | 119.5 (2) | C58—C57—H60 | 108.6 |
C25—C26—H15 | 120.2 | H59—C57—H60 | 107.6 |
C27—C26—H15 | 120.2 | C59—C58—C57 | 114.9 (5) |
N28—C27—C26 | 122.8 (2) | C59—C58—H61 | 108.5 |
N28—C27—H16 | 118.6 | C57—C58—H61 | 108.5 |
C26—C27—H16 | 118.6 | C59—C58—H62 | 108.5 |
N34—C33—S30 | 121.19 (15) | C57—C58—H62 | 108.5 |
N34—C33—S29 | 119.23 (15) | H61—C58—H62 | 107.5 |
S30—C33—S29 | 119.57 (11) | C60—C59—C58 | 115.8 (7) |
N36—C35—S32 | 120.41 (16) | C60—C59—H63 | 108.3 |
N36—C35—S31 | 120.30 (16) | C58—C59—H63 | 108.3 |
S32—C35—S31 | 119.29 (12) | C60—C59—H64 | 108.3 |
N34—C37—C38 | 114.7 (2) | C58—C59—H64 | 108.3 |
N34—C37—H17 | 108.6 | H63—C59—H64 | 107.4 |
C38—C37—H17 | 108.6 | C59—C60—H65 | 109.5 |
N34—C37—H18 | 108.6 | C59—C60—H66 | 109.5 |
C38—C37—H18 | 108.6 | H65—C60—H66 | 109.5 |
H17—C37—H18 | 107.6 | C59—C60—H67 | 109.5 |
C39—C38—C37 | 115.8 (2) | H65—C60—H67 | 109.5 |
C39—C38—H19 | 108.3 | H66—C60—H67 | 109.5 |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Zn(C9H18NS2)2(C12H8N2)]·0.5C2H6O | [Ca(C13H26NS2)2(C12H8N2)2] |
Mr | 677.34 | 921.42 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 10.006 (4), 13.347 (2), 15.531 (2) | 11.875 (4), 13.129 (2), 17.547 (4) |
α, β, γ (°) | 103.71 (1), 102.78 (2), 108.37 (2) | 72.29 (1), 80.91 (2), 84.20 (2) |
V (Å3) | 1811.2 (8) | 2569.2 (11) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.94 | 0.32 |
Crystal size (mm) | 0.32 × 0.29 × 0.28 | 0.30 × 0.28 × 0.25 |
Data collection | ||
Diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6383, 6383, 5232 | 9086, 9086, 7339 |
Rint | 0.000 | 0.000 |
(sin θ/λ)max (Å−1) | 0.595 | 0.596 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.149, 1.21 | 0.042, 0.155, 1.07 |
No. of reflections | 6383 | 9086 |
No. of parameters | 379 | 550 |
No. of restraints | 2 | 316 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.79, −0.28 | 0.82, −0.24 |
Computer programs: CAD-4 Operations Manual (Enraf-Nonius, 1977), CAD-4 Operations Manual, MolEN (Fair, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-NT (Sheldrick, 1999), SHELXL97.
Zn—N14 | 2.178 (2) | Zn—S15 | 2.4793 (11) |
Zn—N1 | 2.284 (2) | Zn—S16 | 2.5083 (9) |
Zn—S17 | 2.4605 (10) | Zn—S18 | 2.6012 (14) |
N14—Zn—N1 | 73.48 (8) | N14—Zn—S18 | 86.24 (6) |
N1—Zn—S15 | 85.01 (7) | S17—Zn—S18 | 69.90 (4) |
S17—Zn—S15 | 103.22 (4) | S15—Zn—S18 | 165.37 (3) |
S15—Zn—S16 | 71.92 (3) | S16—Zn—S18 | 97.29 (4) |
Ca—N28 | 2.5571 (15) | Ca—S29 | 2.8981 (11) |
Ca—N14 | 2.5616 (15) | Ca—S31 | 2.9114 (11) |
Ca—N15 | 2.6145 (18) | Ca—S32 | 2.9963 (8) |
Ca—N1 | 2.6333 (19) | Ca—S30 | 3.0371 (8) |
N28—Ca—N15 | 63.48 (5) | S29—Ca—S32 | 85.16 (3) |
N28—Ca—N1 | 78.98 (6) | S31—Ca—S32 | 59.85 (3) |
N14—Ca—N1 | 63.20 (5) | N14—Ca—S30 | 78.73 (4) |
N15—Ca—S29 | 71.63 (4) | S29—Ca—S30 | 59.54 (2) |
N1—Ca—S31 | 73.59 (5) | S31—Ca—S30 | 83.69 (3) |
N28—Ca—S32 | 78.80 (4) |
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During an investigation of the antioxidant properties of metal dithiocarbamate additives (Becker & Knorr, 1996; Becker et al., 1996) in vegetable oils for technical applications, a series of model compounds has been prepared. The crystal structures of zinc dithiocarbamates designed for improved activity (Reck & Becker, 2003a) and of oxidized derivatives believed to play a role as intermediates in the antioxidant action of zinc dithiocarbamates (Reck et al., 1995; Reck & Becker, 2003b) have already been published. Against this background, we present here the crystal structures of the two title complexes, (I) and (II). \sch
While calcium dithiocarbamates themselves were seen to be unstable, the 1,10-phenanthroline complex of calcium dihexyldithiocarbamate, (II), is stable and displays a rare eight-coordination, with four N atoms of two phenanthroline ligands and four S atoms of two dihexyldithiocarbamate ligands. These eight atoms form a highly distorted cube. The average Ca—N and Ca—S distances are 2.59 (3) and 2.96 (6) Å, respectively. The bite distances of the phenanthroline and dithiocarbamate ligands are N1.·N14 2.723 (5), N15.·N28 2.721 (5), S29.·S30 2.949 (3) and S31.·S32 2.948 (3) Å.
In contrast with (II), the zinc dithiocarbamate forms a complex, (I), with only one 1,10-phenanthroline ligand. Two N atoms of the phenanthroline ligand and four S atoms of two dibutyldithiocarbamate molecules form a distorted octahedron. The coordinative bonds in (I) are significantly shorter than the corresponding bonds in (II). The average Zn—N and Zn—S distances are 2.23 (7) and 2.51 (6) Å, respectively. The bite distances of the ligands in (I) are N1.·N14 2.671 (5), S15.·S16 2.929 (3) and S17.·S18 2.902 (3) Å.
The phenanthroline ligands in (I) and (II) are almost planar; the corresponding r.m.s. deviations are 0.035, 0.039 and 0.029 Å, respectively. The dihedral angle between both symmetry-independent phenanthroline molecules in (II) is 78.84 (4)°.
In (I) as well as in (II) there are π–π interactions between symmetry-related phenanthroline ligands. These interactions are defined by the distances between the ring centroids (DC), the distances between the planes through the rings (DP) and the shifts (SH). For compound (I), the numerical values of these parameters are as follows. For ring C5—C10 and ring C9—C13/N14 at (1 − x, −y, 2 − z), DC = 3.632 (4), DP = 3.270 (16) and SH = 1.580 (35) Å. For ring C9—C13/N14 and ring C9—C13/N14 at (1 − x, −y, 2 − z), DC = 3.682 (3), DP = 3.371 (17) and SH = 1.480 (39) Å. For compound (II), these parameters are as follows. For ring C5—C10 and ring C9—C13/N14 at (2 − x, 1 − y, −z), DC = 3.773 (4), DP = 3.719 (15) and SH = 0.634 (92) Å. For ring C19—C24 and ring C23—C27/N28 at (1 − x, −y, −z), DC = 3.744 (3), DP = 3.668 (5) and SH = 0.746 (29) Å.
The crystal structure of (I) contains half an ethanol molecule per complex molecule. The butyl groups in (I) and the hexyl groups in (II) show high displacement parameters, indicating weak hydrophobic interactions between the complex molecules.