Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110009687/pi5004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110009687/pi5004ZnSMesup2.hkl |
CCDC reference: 782726
Data reduction: SORTAV Blessing 1997; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: Volkov et al., (2006); molecular graphics: Volkov et al., (2006); software used to prepare material for publication: Volkov et al., (2006).
C26H22N2S2Zn | F(000) = 1016 |
Mr = 491.99 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9906 reflections |
a = 9.9280 (4) Å | θ = 27.7–52.1° |
b = 19.9226 (8) Å | µ = 1.29 mm−1 |
c = 12.0100 (5) Å | T = 90 K |
β = 107.924 (1)° | Sphere, pale yellow |
V = 2260.18 (16) Å3 | 0.15 mm (radius) |
Z = 4 |
Bruker SMART Apex II CCD Detector diffractometer | 26207 independent reflections |
Radiation source: rotating anode | 21306 reflections with > 3σ(I) |
Graphite monochromator | Rint = 0.0000 |
φ scans | θmax = 52.3°, θmin = 2.0° |
Absorption correction: empirical (using intensity measurements) spherical | h = −22→21 |
Tmin = 0.754, Tmax = 0.781 | k = 0→44 |
293231 measured reflections | l = 0→26 |
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.014 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.017 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0379P)2 + 0.141P] where P = (Fo2 + 2Fc2)/3 |
21306 reflections | (Δ/σ)max = 0.00003 |
837 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Zn(1) | 0.287310 (7) | 0.507532 (3) | 0.230086 (5) | 0.012 | |
S(1) | 0.226142 (7) | 0.616984 (3) | 0.204640 (5) | 0.015 | |
S(2) | 0.222559 (8) | 0.434642 (3) | 0.350058 (6) | 0.017 | |
N(1) | 0.50274 (3) | 0.493770 (12) | 0.24780 (2) | 0.013 | |
N(2) | 0.27238 (3) | 0.454914 (12) | 0.07355 (2) | 0.012 | |
C(1) | 0.61377 (3) | 0.512840 (12) | 0.33614 (2) | 0.016 | |
C(2) | 0.75334 (3) | 0.496864 (14) | 0.34102 (3) | 0.019 | |
C(3) | 0.77728 (3) | 0.459483 (14) | 0.25200 (3) | 0.018 | |
C(4) | 0.66055 (3) | 0.437642 (12) | 0.15836 (2) | 0.014 | |
C(5) | 0.67406 (3) | 0.396265 (14) | 0.06430 (3) | 0.018 | |
C(6) | 0.55733 (3) | 0.374143 (14) | −0.02115 (3) | 0.017 | |
C(7) | 0.41754 (3) | 0.392513 (12) | −0.02074 (2) | 0.014 | |
C(8) | 0.29357 (3) | 0.369352 (14) | −0.10547 (2) | 0.017 | |
C(9) | 0.16322 (3) | 0.389250 (14) | −0.09842 (2) | 0.017 | |
C(10) | 0.15747 (3) | 0.432398 (13) | −0.00754 (2) | 0.015 | |
C(11) | 0.40109 (3) | 0.434829 (10) | 0.068215 (18) | 0.011 | |
C(12) | 0.52446 (3) | 0.456736 (10) | 0.160153 (19) | 0.012 | |
C(13) | 0.18199 (2) | 0.639192 (11) | 0.33256 (2) | 0.012 | |
C(14) | 0.09253 (3) | 0.599965 (12) | 0.37673 (2) | 0.014 | |
C(15) | 0.05412 (3) | 0.621549 (12) | 0.47327 (2) | 0.014 | |
C(16) | 0.10297 (3) | 0.682432 (12) | 0.52901 (2) | 0.013 | |
C(17) | 0.19224 (3) | 0.721347 (12) | 0.48491 (2) | 0.015 | |
C(18) | 0.23139 (3) | 0.700267 (12) | 0.38847 (2) | 0.015 | |
C(19) | 0.27536 (3) | 0.361333 (12) | 0.28908 (2) | 0.014 | |
C(20) | 0.17496 (3) | 0.324279 (14) | 0.20372 (2) | 0.016 | |
C(21) | 0.21519 (3) | 0.269380 (14) | 0.14935 (2) | 0.016 | |
C(22) | 0.35699 (3) | 0.249743 (12) | 0.17769 (2) | 0.015 | |
C(23) | 0.45697 (3) | 0.285552 (13) | 0.26540 (2) | 0.015 | |
C(24) | 0.41715 (3) | 0.340316 (13) | 0.32100 (2) | 0.015 | |
C(25) | 0.06010 (4) | 0.705248 (14) | 0.63267 (2) | 0.02 | |
C(26) | 0.39901 (4) | 0.192671 (17) | 0.11325 (3) | 0.024 | |
H(1) | 0.596214 | 0.541683 | 0.406922 | 0.019079 | |
H(2) | 0.841397 | 0.513639 | 0.413835 | 0.022576 | |
H(3) | 0.884229 | 0.447196 | 0.254112 | 0.021758 | |
H(5) | 0.778377 | 0.382523 | 0.061108 | 0.02113 | |
H(6) | 0.570274 | 0.342318 | −0.090142 | 0.020734 | |
H(8) | 0.300519 | 0.336416 | −0.175097 | 0.020423 | |
H(9) | 0.066774 | 0.3718 | −0.162217 | 0.0209 | |
H(10) | 0.054622 | 0.448032 | −0.003362 | 0.018393 | |
H(14) | 0.052923 | 0.552587 | 0.335486 | 0.016232 | |
H(15) | −0.015119 | 0.590509 | 0.505786 | 0.016901 | |
H(17) | 0.231662 | 0.7687 | 0.526341 | 0.017732 | |
H(18) | 0.300705 | 0.73146 | 0.356337 | 0.017343 | |
H(20) | 0.064427 | 0.338535 | 0.179504 | 0.019136 | |
H(21) | 0.135235 | 0.241366 | 0.084203 | 0.019609 | |
H(23) | 0.567117 | 0.270535 | 0.290694 | 0.018315 | |
H(24) | 0.496353 | 0.366796 | 0.3893 | 0.017956 | |
H(261) | 0.489087 | 0.16691 | 0.166544 | 0.03478 | |
H(251) | 0.062757 | 0.758118 | 0.642506 | 0.04148 | |
H(253) | −0.041837 | 0.687854 | 0.62969 | 0.04539 | |
H(262) | 0.314418 | 0.158668 | 0.078428 | 0.04149 | |
H(263) | 0.431425 | 0.212184 | 0.043583 | 0.03674 | |
H(252) | 0.132637 | 0.684663 | 0.708928 | 0.03658 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn(1) | 0.01443 (3) | 0.01229 (3) | 0.01206 (3) | 0.001129 (19) | 0.00620 (2) | −0.001416 (17) |
S(1) | 0.01847 (2) | 0.013401 (19) | 0.01460 (2) | 0.002679 (16) | 0.009212 (17) | 0.000825 (15) |
S(2) | 0.02446 (3) | 0.01439 (2) | 0.01657 (2) | 0.000138 (19) | 0.01276 (2) | −0.001199 (16) |
N(1) | 0.01337 (7) | 0.01281 (6) | 0.01200 (7) | 0.00014 (6) | 0.00404 (6) | −0.00201 (6) |
N(2) | 0.01208 (7) | 0.01422 (7) | 0.01120 (6) | 0.00110 (6) | 0.00402 (6) | −0.00150 (5) |
C(1) | 0.01633 (9) | 0.01521 (8) | 0.01471 (8) | −0.00132 (6) | 0.00263 (7) | −0.00329 (6) |
C(2) | 0.01480 (9) | 0.01797 (9) | 0.02071 (10) | −0.00170 (7) | 0.00115 (8) | −0.00317 (8) |
C(3) | 0.01261 (9) | 0.01763 (8) | 0.02312 (10) | −0.00017 (7) | 0.00388 (8) | −0.00152 (8) |
C(4) | 0.01233 (8) | 0.01391 (7) | 0.01702 (8) | 0.00097 (6) | 0.00578 (6) | −0.00055 (6) |
C(5) | 0.01543 (9) | 0.01855 (9) | 0.02114 (9) | 0.00264 (7) | 0.00910 (8) | −0.00271 (8) |
C(6) | 0.01828 (10) | 0.01873 (9) | 0.01730 (8) | 0.00281 (7) | 0.00908 (8) | −0.00357 (7) |
C(7) | 0.01601 (9) | 0.01465 (7) | 0.01149 (6) | 0.00171 (6) | 0.00571 (6) | −0.00189 (6) |
C(8) | 0.01970 (10) | 0.01917 (9) | 0.01183 (7) | 0.00106 (7) | 0.00411 (7) | −0.00400 (7) |
C(9) | 0.01700 (10) | 0.02072 (9) | 0.01271 (7) | 0.00010 (7) | 0.00166 (7) | −0.00317 (7) |
C(10) | 0.01309 (8) | 0.01858 (8) | 0.01357 (7) | 0.00124 (6) | 0.00285 (6) | −0.00175 (6) |
C(11) | 0.01266 (7) | 0.01219 (6) | 0.01033 (6) | 0.00118 (5) | 0.00461 (5) | −0.00081 (5) |
C(12) | 0.01203 (7) | 0.01163 (6) | 0.01193 (6) | 0.00054 (5) | 0.00457 (6) | −0.00064 (5) |
C(13) | 0.01334 (7) | 0.01192 (6) | 0.01266 (6) | 0.00036 (6) | 0.00555 (6) | −0.00041 (5) |
C(14) | 0.01597 (8) | 0.01245 (6) | 0.01386 (7) | −0.00220 (6) | 0.00687 (6) | −0.00258 (5) |
C(15) | 0.01675 (8) | 0.01352 (7) | 0.01385 (7) | −0.00318 (6) | 0.00735 (6) | −0.00242 (6) |
C(16) | 0.01614 (8) | 0.01310 (7) | 0.01173 (6) | −0.00150 (6) | 0.00543 (6) | −0.00201 (5) |
C(17) | 0.01771 (8) | 0.01281 (7) | 0.01485 (7) | −0.00322 (6) | 0.00637 (7) | −0.00261 (6) |
C(18) | 0.01627 (8) | 0.01297 (7) | 0.01599 (7) | −0.00243 (6) | 0.00745 (7) | −0.00128 (6) |
C(19) | 0.01770 (9) | 0.01339 (7) | 0.01295 (7) | −0.00010 (6) | 0.00669 (6) | −0.00058 (6) |
C(20) | 0.01550 (9) | 0.01690 (8) | 0.01597 (8) | 0.00023 (7) | 0.00544 (7) | −0.00154 (7) |
C(21) | 0.01682 (9) | 0.01601 (8) | 0.01556 (8) | −0.00100 (7) | 0.00391 (7) | −0.00286 (7) |
C(22) | 0.01799 (9) | 0.01283 (7) | 0.01434 (7) | 0.00070 (6) | 0.00512 (7) | −0.00112 (6) |
C(23) | 0.01597 (9) | 0.01448 (7) | 0.01495 (7) | 0.00102 (6) | 0.00412 (7) | −0.00022 (6) |
C(24) | 0.01729 (9) | 0.01429 (7) | 0.01304 (7) | −0.00094 (7) | 0.00412 (6) | −0.00114 (6) |
C(25) | 0.02845 (12) | 0.01906 (9) | 0.01543 (8) | −0.00325 (8) | 0.01132 (8) | −0.00465 (6) |
C(26) | 0.02708 (12) | 0.01935 (9) | 0.02427 (11) | 0.00420 (9) | 0.00693 (9) | −0.00719 (8) |
ZN(1)—S(1) | 2.2589 (1) | C(13)—C(14) | 1.4039 (3) |
ZN(1)—S(2) | 2.2734 (1) | C(13)—C(18) | 1.4033 (3) |
S(1)—C(13) | 1.7784 (2) | C(14)—C(15) | 1.3953 (3) |
S(2)—C(19) | 1.7834 (3) | C(14)—H(14) | 1.0822 (2) |
N(1)—C(1) | 1.3287 (3) | C(15)—C(16) | 1.3981 (3) |
N(1)—C(12) | 1.3559 (3) | C(15)—H(15) | 1.0829 (2) |
N(2)—C(10) | 1.3294 (3) | C(16)—C(17) | 1.3985 (4) |
N(2)—C(11) | 1.3592 (3) | C(16)—C(25) | 1.5046 (4) |
C(1)—C(2) | 1.4052 (4) | C(17)—C(18) | 1.3950 (4) |
C(1)—H(1) | 1.0837 (3) | C(17)—H(17) | 1.0821 (2) |
C(2)—C(3) | 1.3822 (5) | C(18)—H(18) | 1.0827 (3) |
C(2)—H(2) | 1.0818 (3) | C(19)—C(20) | 1.4002 (4) |
C(3)—C(4) | 1.4124 (4) | C(19)—C(24) | 1.4042 (4) |
C(3)—H(3) | 1.0823 (3) | C(20)—C(21) | 1.3938 (4) |
C(4)—C(5) | 1.4376 (4) | C(20)—H(20) | 1.0831 (3) |
C(4)—C(12) | 1.4102 (3) | C(21)—C(22) | 1.3985 (4) |
C(5)—C(6) | 1.3632 (4) | C(21)—H(21) | 1.0824 (3) |
C(5)—H(5) | 1.0833 (3) | C(22)—C(23) | 1.4001 (4) |
C(6)—C(7) | 1.4367 (4) | C(22)—C(26) | 1.5048 (4) |
C(6)—H(6) | 1.0820 (3) | C(23)—C(24) | 1.3982 (4) |
C(7)—C(8) | 1.4115 (4) | C(23)—H(23) | 1.0831 (3) |
C(7)—C(11) | 1.4094 (3) | C(24)—H(24) | 1.0828 (3) |
C(8)—C(9) | 1.3808 (4) | C(25)—H(251) | 1.0593 (3) |
C(8)—H(8) | 1.0817 (3) | C(25)—H(253) | 1.0599 (3) |
C(9)—C(10) | 1.4043 (4) | C(25)—H(252) | 1.0581 (3) |
C(9)—H(9) | 1.0832 (3) | C(26)—H(261) | 1.0585 (3) |
C(10)—H(10) | 1.0833 (3) | C(26)—H(262) | 1.0597 (4) |
C(11)—C(12) | 1.4414 (3) | C(26)—H(263) | 1.0586 (4) |
S(1)—ZN(1)—S(2) | 125.850 (3) | C(13)—C(14)—H(14) | 119.71 (2) |
ZN(1)—S(1)—C(13) | 104.523 (8) | C(15)—C(14)—H(14) | 119.70 (2) |
ZN(1)—S(2)—C(19) | 94.972 (8) | C(14)—C(15)—C(16) | 121.47 (2) |
C(1)—N(1)—C(12) | 118.97 (2) | C(14)—C(15)—H(15) | 119.33 (2) |
C(10)—N(2)—C(11) | 118.25 (2) | C(16)—C(15)—H(15) | 119.20 (2) |
N(1)—C(1)—C(2) | 122.25 (3) | C(15)—C(16)—C(17) | 117.81 (2) |
N(1)—C(1)—H(1) | 118.93 (3) | C(15)—C(16)—C(25) | 120.90 (2) |
C(2)—C(1)—H(1) | 118.82 (3) | C(17)—C(16)—C(25) | 121.30 (2) |
C(1)—C(2)—C(3) | 119.46 (3) | C(16)—C(17)—C(18) | 121.23 (2) |
C(1)—C(2)—H(2) | 120.32 (3) | C(16)—C(17)—H(17) | 119.40 (2) |
C(3)—C(2)—H(2) | 120.21 (3) | C(18)—C(17)—H(17) | 119.37 (2) |
C(2)—C(3)—C(4) | 119.18 (3) | C(13)—C(18)—C(17) | 120.84 (2) |
C(2)—C(3)—H(3) | 120.31 (3) | C(13)—C(18)—H(18) | 119.60 (2) |
C(4)—C(3)—H(3) | 120.51 (3) | C(17)—C(18)—H(18) | 119.55 (2) |
C(3)—C(4)—C(5) | 123.38 (3) | S(2)—C(19)—C(20) | 119.96 (2) |
C(3)—C(4)—C(12) | 117.38 (2) | S(2)—C(19)—C(24) | 121.92 (2) |
C(5)—C(4)—C(12) | 119.22 (2) | C(20)—C(19)—C(24) | 118.07 (2) |
C(4)—C(5)—C(6) | 120.91 (3) | C(19)—C(20)—C(21) | 120.98 (3) |
C(4)—C(5)—H(5) | 119.61 (3) | C(19)—C(20)—H(20) | 119.50 (3) |
C(6)—C(5)—H(5) | 119.48 (3) | C(21)—C(20)—H(20) | 119.52 (3) |
C(5)—C(6)—C(7) | 120.89 (2) | C(20)—C(21)—C(22) | 121.17 (3) |
C(5)—C(6)—H(6) | 119.49 (3) | C(20)—C(21)—H(21) | 119.42 (3) |
C(7)—C(6)—H(6) | 119.63 (3) | C(22)—C(21)—H(21) | 119.41 (3) |
C(6)—C(7)—C(8) | 122.90 (2) | C(21)—C(22)—C(23) | 117.91 (2) |
C(6)—C(7)—C(11) | 119.50 (2) | C(21)—C(22)—C(26) | 120.25 (3) |
C(8)—C(7)—C(11) | 117.60 (2) | C(23)—C(22)—C(26) | 121.83 (3) |
C(7)—C(8)—C(9) | 119.19 (2) | C(22)—C(23)—C(24) | 121.18 (3) |
C(7)—C(8)—H(8) | 120.45 (3) | C(22)—C(23)—H(23) | 119.41 (2) |
C(9)—C(8)—H(8) | 120.36 (3) | C(24)—C(23)—H(23) | 119.41 (3) |
C(8)—C(9)—C(10) | 119.11 (3) | C(19)—C(24)—C(23) | 120.62 (2) |
C(8)—C(9)—H(9) | 120.37 (3) | C(19)—C(24)—H(24) | 119.66 (2) |
C(10)—C(9)—H(9) | 120.51 (3) | C(23)—C(24)—H(24) | 119.73 (3) |
N(2)—C(10)—C(9) | 123.02 (3) | C(16)—C(25)—H(251) | 112.90 (2) |
N(2)—C(10)—H(10) | 118.53 (2) | C(16)—C(25)—H(253) | 112.56 (2) |
C(9)—C(10)—H(10) | 118.45 (2) | C(16)—C(25)—H(252) | 107.98 (3) |
N(2)—C(11)—C(7) | 122.81 (2) | H(251)—C(25)—H(253) | 108.64 (3) |
N(2)—C(11)—C(12) | 117.67 (2) | H(251)—C(25)—H(252) | 107.57 (2) |
C(7)—C(11)—C(12) | 119.50 (2) | H(253)—C(25)—H(252) | 106.91 (2) |
N(1)—C(12)—C(4) | 122.73 (2) | C(22)—C(26)—H(261) | 111.82 (3) |
N(1)—C(12)—C(11) | 117.31 (2) | C(22)—C(26)—H(262) | 112.00 (3) |
C(4)—C(12)—C(11) | 119.93 (2) | C(22)—C(26)—H(263) | 109.20 (3) |
S(1)—C(13)—C(14) | 122.734 (18) | H(261)—C(26)—H(262) | 110.37 (3) |
S(1)—C(13)—C(18) | 119.100 (18) | H(261)—C(26)—H(263) | 104.49 (3) |
C(14)—C(13)—C(18) | 118.06 (2) | H(262)—C(26)—H(263) | 108.64 (3) |
C(13)—C(14)—C(15) | 120.59 (2) |