metal-organic compounds
The title compound, [Zn(C12H10N2O2S)2(C2H6OS)], is monomeric with the Zn atom in a five-coordinate environment. The geometry of the polyhedron is distorted trigonal bipyramidal, with angles of the equatorial atoms about the central Zn atom in the range 77.84 (10)–126.66 (12) Å. The O—Zn—O axial bond angle is 173.12 (12)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025194/cv6242sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025194/cv6242Isup2.hkl |
CCDC reference: 227746
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Crystal data top
[Zn(C12H10N2O2S)2(C2H6OS)] | Z = 2 |
Mr = 610.02 | F(000) = 628 |
Triclinic, P1 | Dx = 1.470 Mg m−3 |
a = 10.4060 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.640 (2) Å | Cell parameters from 5500 reflections |
c = 13.152 (2) Å | θ = 1.5–26.0° |
α = 93.067 (4)° | µ = 1.16 mm−1 |
β = 98.772 (4)° | T = 293 K |
γ = 105.796 (4)° | Block, yellow |
V = 1377.9 (4) Å3 | 0.34 × 0.28 × 0.10 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5322 independent reflections |
Radiation source: fine-focus sealed tube | 4164 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 83.66 pixels mm-1 | θmax = 26.0°, θmin = 1.5° |
ω scans | h = −12→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.693, Tmax = 0.892 | l = −16→16 |
10224 measured reflections |
Refinement top
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0898P)2] where P = (Fo2 + 2Fc2)/3 |
5322 reflections | (Δ/σ)max < 0.001 |
344 parameters | Δρmax = 0.56 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Zn1 | 0.21612 (4) | 0.31041 (3) | 0.17871 (3) | 0.04759 (16) | |
S1 | 0.57587 (11) | 0.73894 (9) | 0.36371 (7) | 0.0614 (3) | |
S2 | −0.24350 (11) | 0.07357 (10) | 0.29388 (10) | 0.0748 (3) | |
S3A | 0.30698 (15) | 0.28592 (14) | −0.03581 (10) | 0.0804 (6) | 0.923 (4) |
S3B | 0.254 (2) | 0.185 (2) | −0.026 (3) | 0.121 (11) | 0.077 (4) |
O1 | 0.1665 (2) | 0.4641 (2) | 0.11215 (19) | 0.0581 (6) | |
O2 | 0.3145 (3) | 0.8089 (2) | 0.1509 (2) | 0.0611 (7) | |
O3 | 0.2424 (4) | 0.2207 (3) | 0.0494 (2) | 0.0775 (9) | |
O4 | 0.2546 (2) | 0.1625 (2) | 0.25925 (19) | 0.0545 (6) | |
O5 | 0.2640 (3) | −0.0574 (3) | 0.3475 (3) | 0.0886 (10) | |
N1 | 0.3594 (3) | 0.5867 (2) | 0.2225 (2) | 0.0485 (7) | |
N2 | 0.3690 (3) | 0.4667 (3) | 0.2509 (2) | 0.0476 (7) | |
N3 | 0.0278 (3) | 0.1196 (3) | 0.2715 (2) | 0.0512 (7) | |
N4 | 0.0368 (3) | 0.2328 (3) | 0.2247 (2) | 0.0481 (7) | |
C1 | 0.1199 (4) | 0.7072 (4) | 0.0504 (3) | 0.0611 (10) | |
H1B | 0.0448 | 0.6418 | 0.0157 | 0.073* | |
C2 | 0.1455 (5) | 0.8436 (4) | 0.0447 (3) | 0.0717 (11) | |
H2A | 0.0907 | 0.8858 | 0.0056 | 0.086* | |
C3 | 0.2617 (5) | 0.8992 (4) | 0.1057 (3) | 0.0670 (11) | |
H3B | 0.3027 | 0.9893 | 0.1164 | 0.080* | |
C4 | 0.2244 (3) | 0.6900 (3) | 0.1152 (3) | 0.0488 (8) | |
C5 | 0.2520 (3) | 0.5717 (3) | 0.1520 (3) | 0.0465 (8) | |
C6 | 0.4681 (3) | 0.4682 (3) | 0.3227 (3) | 0.0492 (8) | |
H6A | 0.4720 | 0.3865 | 0.3424 | 0.059* | |
C7 | 0.5727 (4) | 0.5771 (3) | 0.3761 (3) | 0.0517 (8) | |
C8 | 0.7174 (5) | 0.7928 (4) | 0.4550 (3) | 0.0766 (13) | |
H8A | 0.7598 | 0.8810 | 0.4770 | 0.092* | |
C9 | 0.7611 (4) | 0.6960 (5) | 0.4914 (3) | 0.0720 (12) | |
H9A | 0.8389 | 0.7095 | 0.5409 | 0.086* | |
C10 | 0.6800 (4) | 0.5712 (4) | 0.4490 (3) | 0.0589 (9) | |
C11 | 0.7105 (5) | 0.4482 (5) | 0.4782 (4) | 0.0813 (13) | |
H11A | 0.6423 | 0.3742 | 0.4399 | 0.122* | |
H11B | 0.7112 | 0.4426 | 0.5509 | 0.122* | |
H11C | 0.7977 | 0.4482 | 0.4626 | 0.122* | |
C12 | 0.0558 (5) | −0.1095 (4) | 0.3753 (3) | 0.0768 (12) | |
H12A | −0.0327 | −0.1079 | 0.3772 | 0.092* | |
C13 | 0.2389 (7) | −0.1689 (6) | 0.3942 (5) | 0.114 (2) | |
H13A | 0.3015 | −0.2158 | 0.4106 | 0.137* | |
C14 | 0.1161 (7) | −0.2027 (5) | 0.4134 (4) | 0.1016 (17) | |
H14A | 0.0764 | −0.2749 | 0.4461 | 0.122* | |
C15 | 0.1477 (4) | −0.0231 (4) | 0.3355 (3) | 0.0546 (9) | |
C17 | −0.0695 (3) | 0.2736 (3) | 0.2118 (3) | 0.0501 (8) | |
H17A | −0.0594 | 0.3524 | 0.1823 | 0.060* | |
C18 | −0.2004 (3) | 0.2162 (3) | 0.2359 (3) | 0.0524 (8) | |
C19 | −0.4056 (4) | 0.0814 (5) | 0.2858 (4) | 0.0878 (15) | |
H19A | −0.4727 | 0.0198 | 0.3105 | 0.105* | |
C20 | −0.4267 (4) | 0.1841 (4) | 0.2410 (4) | 0.0806 (14) | |
H20A | −0.5103 | 0.2015 | 0.2309 | 0.097* | |
C21 | −0.3113 (4) | 0.2640 (4) | 0.2101 (3) | 0.0635 (10) | |
C22 | −0.3061 (5) | 0.3865 (5) | 0.1630 (4) | 0.0984 (17) | |
H22A | −0.2165 | 0.4243 | 0.1489 | 0.148* | |
H22B | −0.3281 | 0.4469 | 0.2097 | 0.148* | |
H22C | −0.3703 | 0.3687 | 0.0996 | 0.148* | |
C23 | 0.4115 (6) | 0.1870 (7) | −0.0688 (4) | 0.121 (2) | |
H23A | 0.4882 | 0.2002 | −0.0144 | 0.181* | 0.923 (4) |
H23B | 0.3599 | 0.0962 | −0.0777 | 0.181* | 0.923 (4) |
H23C | 0.4424 | 0.2114 | −0.1320 | 0.181* | 0.923 (4) |
H23D | 0.4670 | 0.1599 | −0.0140 | 0.181* | 0.077 (4) |
H23E | 0.3956 | 0.1279 | −0.1301 | 0.181* | 0.077 (4) |
H23F | 0.4568 | 0.2742 | −0.0824 | 0.181* | 0.077 (4) |
C24 | 0.1827 (6) | 0.2371 (6) | −0.1477 (4) | 0.1080 (18) | |
H24A | 0.1146 | 0.2817 | −0.1444 | 0.162* | 0.923 (4) |
H24C | 0.1418 | 0.1440 | −0.1525 | 0.162* | 0.923 (4) |
H24D | 0.2239 | 0.2588 | −0.2074 | 0.162* | 0.923 (4) |
H24B | 0.0933 | 0.2428 | −0.1431 | 0.162* | 0.077 (4) |
H24E | 0.2392 | 0.3218 | −0.1575 | 0.162* | 0.077 (4) |
H24F | 0.1780 | 0.1755 | −0.2052 | 0.162* | 0.077 (4) |
C16 | 0.1465 (3) | 0.0945 (3) | 0.2850 (2) | 0.0470 (8) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0349 (2) | 0.0439 (2) | 0.0623 (3) | 0.00863 (16) | 0.00945 (17) | 0.00098 (16) |
S1 | 0.0620 (6) | 0.0520 (5) | 0.0608 (6) | 0.0036 (4) | 0.0060 (4) | 0.0031 (4) |
S2 | 0.0550 (6) | 0.0645 (6) | 0.1086 (9) | 0.0129 (5) | 0.0302 (6) | 0.0153 (5) |
S3A | 0.0929 (10) | 0.0724 (10) | 0.0751 (8) | 0.0112 (7) | 0.0342 (7) | 0.0103 (6) |
S3B | 0.096 (14) | 0.066 (13) | 0.24 (3) | 0.055 (11) | 0.077 (17) | 0.045 (14) |
O1 | 0.0463 (14) | 0.0487 (13) | 0.0697 (16) | 0.0072 (11) | −0.0072 (12) | 0.0048 (11) |
O2 | 0.0566 (16) | 0.0466 (13) | 0.0733 (16) | 0.0133 (11) | −0.0052 (13) | 0.0016 (11) |
O3 | 0.104 (3) | 0.0652 (18) | 0.0727 (19) | 0.0245 (17) | 0.0459 (18) | −0.0004 (14) |
O4 | 0.0387 (13) | 0.0571 (14) | 0.0733 (16) | 0.0200 (11) | 0.0132 (11) | 0.0127 (11) |
O5 | 0.083 (2) | 0.094 (2) | 0.121 (3) | 0.0560 (18) | 0.0441 (19) | 0.0512 (19) |
N1 | 0.0396 (15) | 0.0400 (14) | 0.0629 (17) | 0.0099 (11) | 0.0028 (13) | 0.0032 (12) |
N2 | 0.0320 (14) | 0.0464 (15) | 0.0631 (17) | 0.0104 (11) | 0.0051 (12) | 0.0052 (12) |
N3 | 0.0406 (16) | 0.0536 (16) | 0.0607 (17) | 0.0145 (13) | 0.0092 (13) | 0.0102 (13) |
N4 | 0.0330 (14) | 0.0515 (15) | 0.0604 (17) | 0.0127 (12) | 0.0082 (12) | 0.0077 (12) |
C1 | 0.054 (2) | 0.058 (2) | 0.065 (2) | 0.0122 (17) | −0.0013 (18) | 0.0076 (16) |
C2 | 0.078 (3) | 0.062 (2) | 0.075 (3) | 0.028 (2) | −0.002 (2) | 0.0101 (19) |
C3 | 0.076 (3) | 0.0440 (19) | 0.078 (3) | 0.0173 (19) | 0.004 (2) | 0.0069 (17) |
C4 | 0.0452 (19) | 0.0486 (18) | 0.0521 (19) | 0.0122 (15) | 0.0098 (15) | 0.0015 (14) |
C5 | 0.0386 (18) | 0.0474 (17) | 0.0543 (19) | 0.0122 (14) | 0.0111 (15) | 0.0037 (14) |
C6 | 0.0414 (19) | 0.0479 (18) | 0.061 (2) | 0.0167 (14) | 0.0095 (16) | 0.0061 (14) |
C7 | 0.0436 (19) | 0.059 (2) | 0.0520 (19) | 0.0118 (15) | 0.0100 (15) | 0.0058 (15) |
C8 | 0.079 (3) | 0.066 (3) | 0.065 (3) | −0.005 (2) | 0.002 (2) | −0.0024 (19) |
C9 | 0.049 (2) | 0.097 (3) | 0.054 (2) | 0.001 (2) | −0.0030 (18) | −0.001 (2) |
C10 | 0.048 (2) | 0.080 (3) | 0.0489 (19) | 0.0166 (18) | 0.0122 (16) | 0.0081 (17) |
C11 | 0.071 (3) | 0.095 (3) | 0.081 (3) | 0.037 (3) | −0.004 (2) | 0.016 (2) |
C12 | 0.064 (3) | 0.077 (3) | 0.093 (3) | 0.020 (2) | 0.019 (2) | 0.031 (2) |
C13 | 0.130 (5) | 0.122 (5) | 0.141 (5) | 0.087 (4) | 0.061 (4) | 0.080 (4) |
C14 | 0.108 (4) | 0.090 (4) | 0.125 (4) | 0.038 (3) | 0.041 (4) | 0.059 (3) |
C15 | 0.055 (2) | 0.061 (2) | 0.053 (2) | 0.0242 (17) | 0.0114 (17) | 0.0037 (16) |
C17 | 0.0377 (18) | 0.0536 (19) | 0.060 (2) | 0.0142 (15) | 0.0104 (15) | 0.0052 (15) |
C18 | 0.0381 (18) | 0.058 (2) | 0.061 (2) | 0.0149 (15) | 0.0099 (15) | −0.0048 (15) |
C19 | 0.050 (3) | 0.082 (3) | 0.135 (4) | 0.009 (2) | 0.043 (3) | 0.006 (3) |
C20 | 0.045 (2) | 0.074 (3) | 0.124 (4) | 0.018 (2) | 0.025 (2) | −0.020 (3) |
C21 | 0.042 (2) | 0.069 (2) | 0.082 (3) | 0.0203 (18) | 0.0156 (18) | −0.0089 (19) |
C22 | 0.074 (3) | 0.111 (4) | 0.132 (5) | 0.057 (3) | 0.022 (3) | 0.025 (3) |
C23 | 0.091 (4) | 0.196 (7) | 0.096 (4) | 0.071 (4) | 0.028 (3) | 0.011 (4) |
C24 | 0.092 (4) | 0.144 (5) | 0.096 (4) | 0.041 (4) | 0.019 (3) | 0.026 (3) |
C16 | 0.0437 (19) | 0.0506 (18) | 0.0458 (17) | 0.0138 (15) | 0.0060 (14) | 0.0011 (13) |
Geometric parameters (Å, º) top
Zn1—O3 | 1.997 (3) | C7—C10 | 1.374 (5) |
Zn1—N4 | 2.022 (3) | C8—C9 | 1.319 (7) |
Zn1—N2 | 2.032 (3) | C8—H8A | 0.9300 |
Zn1—O4 | 2.038 (2) | C9—C10 | 1.397 (5) |
Zn1—O1 | 2.045 (2) | C9—H9A | 0.9300 |
S1—C8 | 1.693 (4) | C10—C11 | 1.485 (6) |
S1—C7 | 1.730 (4) | C11—H11A | 0.9600 |
S2—C19 | 1.699 (5) | C11—H11B | 0.9600 |
S2—C18 | 1.716 (4) | C11—H11C | 0.9600 |
S3A—O3 | 1.500 (3) | C12—C15 | 1.326 (5) |
S3A—C24 | 1.755 (6) | C12—C14 | 1.387 (7) |
S3A—C23 | 1.788 (6) | C12—H12A | 0.9300 |
S3A—H23F | 1.7921 | C13—C14 | 1.297 (8) |
S3A—H24E | 1.7527 | C13—H13A | 0.9300 |
S3B—O3 | 1.07 (3) | C14—H14A | 0.9300 |
S3B—C23 | 1.81 (2) | C15—C16 | 1.451 (5) |
S3B—C24 | 1.84 (3) | C17—C18 | 1.425 (5) |
S3B—H23B | 1.8186 | C17—H17A | 0.9300 |
O1—C5 | 1.271 (4) | C18—C21 | 1.387 (5) |
O2—C3 | 1.352 (5) | C19—C20 | 1.322 (7) |
O2—C4 | 1.362 (4) | C19—H19A | 0.9300 |
O4—C16 | 1.266 (4) | C20—C21 | 1.399 (6) |
O5—C13 | 1.346 (6) | C20—H20A | 0.9300 |
O5—C15 | 1.346 (5) | C21—C22 | 1.465 (6) |
N1—C5 | 1.306 (4) | C22—H22A | 0.9600 |
N1—N2 | 1.374 (4) | C22—H22B | 0.9600 |
N2—C6 | 1.283 (4) | C22—H22C | 0.9600 |
N3—C16 | 1.321 (4) | C23—H23A | 0.9600 |
N3—N4 | 1.370 (4) | C23—H23B | 0.9600 |
N4—C17 | 1.285 (4) | C23—H23C | 0.9599 |
C1—C4 | 1.335 (5) | C23—H23D | 0.9600 |
C1—C2 | 1.411 (5) | C23—H23E | 0.9600 |
C1—H1B | 0.9300 | C23—H23F | 0.9599 |
C2—C3 | 1.311 (6) | C24—H24A | 0.9600 |
C2—H2A | 0.9300 | C24—H24C | 0.9600 |
C3—H3B | 0.9300 | C24—H24D | 0.9600 |
C4—C5 | 1.457 (5) | C24—H24B | 0.9601 |
C6—C7 | 1.419 (5) | C24—H24E | 0.9600 |
C6—H6A | 0.9300 | C24—H24F | 0.9599 |
O3—Zn1—N4 | 115.33 (12) | C13—C14—H14A | 126.8 |
O3—Zn1—N2 | 118.01 (13) | C12—C14—H14A | 126.8 |
N4—Zn1—N2 | 126.66 (12) | C12—C15—O5 | 109.3 (4) |
O3—Zn1—O4 | 89.96 (12) | C12—C15—C16 | 133.6 (4) |
N4—Zn1—O4 | 78.15 (10) | O5—C15—C16 | 117.2 (3) |
N2—Zn1—O4 | 101.19 (10) | N4—C17—C18 | 129.8 (3) |
O3—Zn1—O1 | 96.51 (12) | N4—C17—H17A | 115.1 |
N4—Zn1—O1 | 96.89 (11) | C18—C17—H17A | 115.1 |
N2—Zn1—O1 | 77.84 (10) | C21—C18—C17 | 124.4 (4) |
O4—Zn1—O1 | 173.12 (10) | C21—C18—S2 | 111.3 (3) |
C8—S1—C7 | 91.4 (2) | C17—C18—S2 | 124.2 (3) |
C19—S2—C18 | 90.8 (2) | C20—C19—S2 | 113.2 (3) |
O3—S3A—C24 | 105.7 (3) | C20—C19—H19A | 123.4 |
O3—S3A—C23 | 104.2 (3) | S2—C19—H19A | 123.4 |
C24—S3A—C23 | 96.8 (3) | C19—C20—C21 | 113.7 (4) |
O3—S3A—H23F | 129.8 | C19—C20—H20A | 123.1 |
C24—S3A—H23F | 102.3 | C21—C20—H20A | 123.1 |
C23—S3A—H23F | 31.1 | C18—C21—C20 | 111.0 (4) |
O3—S3A—H24E | 132.5 | C18—C21—C22 | 124.4 (4) |
C24—S3A—H24E | 31.8 | C20—C21—C22 | 124.5 (4) |
C23—S3A—H24E | 102.0 | C21—C22—H22A | 109.5 |
H23F—S3A—H24E | 90.7 | C21—C22—H22B | 109.5 |
O3—S3B—C23 | 127 (2) | H22A—C22—H22B | 109.5 |
O3—S3B—C24 | 123.9 (13) | C21—C22—H22C | 109.5 |
C23—S3B—C24 | 93.0 (14) | H22A—C22—H22C | 109.5 |
O3—S3B—H23B | 136.9 | H22B—C22—H22C | 109.5 |
C23—S3B—H23B | 30.7 | S3A—C23—S3B | 35.4 (6) |
C24—S3B—H23B | 98.0 | S3A—C23—H23A | 109.6 |
C5—O1—Zn1 | 110.0 (2) | S3B—C23—H23A | 114.9 |
C3—O2—C4 | 105.9 (3) | S3A—C23—H23B | 109.4 |
S3B—O3—S3A | 46.7 (11) | S3B—C23—H23B | 75.1 |
S3B—O3—Zn1 | 171.4 (11) | H23A—C23—H23B | 109.5 |
S3A—O3—Zn1 | 126.41 (19) | S3A—C23—H23C | 109.4 |
C16—O4—Zn1 | 109.8 (2) | S3B—C23—H23C | 130.7 |
C13—O5—C15 | 105.8 (4) | H23A—C23—H23C | 109.5 |
C5—N1—N2 | 110.3 (2) | H23B—C23—H23C | 109.5 |
C6—N2—N1 | 116.4 (3) | S3A—C23—H23D | 118.7 |
C6—N2—Zn1 | 128.6 (2) | S3B—C23—H23D | 107.4 |
N1—N2—Zn1 | 114.91 (19) | H23A—C23—H23D | 25.7 |
C16—N3—N4 | 110.0 (3) | H23B—C23—H23D | 83.9 |
C17—N4—N3 | 117.0 (3) | H23C—C23—H23D | 122.0 |
C17—N4—Zn1 | 128.2 (2) | S3A—C23—H23E | 127.1 |
N3—N4—Zn1 | 114.8 (2) | S3B—C23—H23E | 111.1 |
C4—C1—C2 | 106.8 (3) | H23A—C23—H23E | 123.4 |
C4—C1—H1B | 126.6 | H23B—C23—H23E | 54.1 |
C2—C1—H1B | 126.6 | H23C—C23—H23E | 55.4 |
C3—C2—C1 | 106.3 (4) | H23D—C23—H23E | 109.5 |
C3—C2—H2A | 126.8 | S3A—C23—H23F | 74.7 |
C1—C2—H2A | 126.8 | S3B—C23—H23F | 110.0 |
C2—C3—O2 | 111.4 (3) | H23A—C23—H23F | 84.0 |
C2—C3—H3B | 124.3 | H23B—C23—H23F | 162.5 |
O2—C3—H3B | 124.3 | H23C—C23—H23F | 54.2 |
C1—C4—O2 | 109.5 (3) | H23D—C23—H23F | 109.5 |
C1—C4—C5 | 131.4 (3) | H23E—C23—H23F | 109.5 |
O2—C4—C5 | 119.1 (3) | S3A—C24—S3B | 35.3 (7) |
O1—C5—N1 | 127.0 (3) | S3A—C24—H24A | 109.5 |
O1—C5—C4 | 115.6 (3) | S3B—C24—H24A | 116.6 |
N1—C5—C4 | 117.4 (3) | S3A—C24—H24C | 109.5 |
N2—C6—C7 | 129.0 (3) | S3B—C24—H24C | 74.8 |
N2—C6—H6A | 115.5 | H24A—C24—H24C | 109.5 |
C7—C6—H6A | 115.5 | S3A—C24—H24D | 109.5 |
C10—C7—C6 | 126.0 (3) | S3B—C24—H24D | 129.1 |
C10—C7—S1 | 110.1 (3) | H24A—C24—H24D | 109.5 |
C6—C7—S1 | 123.8 (3) | H24C—C24—H24D | 109.5 |
C9—C8—S1 | 112.6 (3) | S3A—C24—H24B | 117.7 |
C9—C8—H8A | 123.7 | S3B—C24—H24B | 108.5 |
S1—C8—H8A | 123.7 | H24A—C24—H24B | 25.0 |
C8—C9—C10 | 113.9 (4) | H24C—C24—H24B | 84.6 |
C8—C9—H9A | 123.0 | H24D—C24—H24B | 122.4 |
C10—C9—H9A | 123.0 | S3A—C24—H24E | 74.0 |
C7—C10—C9 | 112.0 (4) | S3B—C24—H24E | 109.0 |
C7—C10—C11 | 124.8 (4) | H24A—C24—H24E | 84.6 |
C9—C10—C11 | 123.2 (4) | H24C—C24—H24E | 162.4 |
C10—C11—H11A | 109.5 | H24D—C24—H24E | 54.3 |
C10—C11—H11B | 109.5 | H24B—C24—H24E | 109.5 |
H11A—C11—H11B | 109.5 | S3A—C24—H24F | 128.4 |
C10—C11—H11C | 109.5 | S3B—C24—H24F | 110.9 |
H11A—C11—H11C | 109.5 | H24A—C24—H24F | 122.1 |
H11B—C11—H11C | 109.5 | H24C—C24—H24F | 54.4 |
C15—C12—C14 | 107.3 (5) | H24D—C24—H24F | 55.2 |
C15—C12—H12A | 126.4 | H24B—C24—H24F | 109.5 |
C14—C12—H12A | 126.4 | H24E—C24—H24F | 109.5 |
C14—C13—O5 | 111.3 (5) | O4—C16—N3 | 126.6 (3) |
C14—C13—H13A | 124.4 | O4—C16—C15 | 119.2 (3) |
O5—C13—H13A | 124.4 | N3—C16—C15 | 114.2 (3) |
C13—C14—C12 | 106.4 (4) | ||
O3—Zn1—O1—C5 | −119.2 (2) | C1—C4—C5—O1 | 4.4 (6) |
N4—Zn1—O1—C5 | 124.2 (2) | O2—C4—C5—O1 | −177.1 (3) |
N2—Zn1—O1—C5 | −1.9 (2) | C1—C4—C5—N1 | −174.7 (4) |
O4—Zn1—O1—C5 | 80.7 (8) | O2—C4—C5—N1 | 3.8 (5) |
C23—S3B—O3—S3A | 64.2 (16) | N1—N2—C6—C7 | −1.6 (6) |
C24—S3B—O3—S3A | −61.3 (13) | Zn1—N2—C6—C7 | −177.6 (3) |
C23—S3B—O3—Zn1 | 104 (9) | N2—C6—C7—C10 | −176.6 (4) |
C24—S3B—O3—Zn1 | −22 (11) | N2—C6—C7—S1 | 7.7 (6) |
C24—S3A—O3—S3B | 52.5 (17) | C8—S1—C7—C10 | −0.3 (3) |
C23—S3A—O3—S3B | −49.0 (17) | C8—S1—C7—C6 | 176.0 (3) |
C24—S3A—O3—Zn1 | −120.7 (3) | C7—S1—C8—C9 | 1.0 (4) |
C23—S3A—O3—Zn1 | 137.8 (3) | S1—C8—C9—C10 | −1.5 (5) |
N4—Zn1—O3—S3B | 105 (9) | C6—C7—C10—C9 | −176.6 (4) |
N2—Zn1—O3—S3B | −76 (9) | S1—C7—C10—C9 | −0.5 (4) |
O4—Zn1—O3—S3B | −178 (9) | C6—C7—C10—C11 | 5.1 (7) |
O1—Zn1—O3—S3B | 4 (9) | S1—C7—C10—C11 | −178.7 (3) |
N4—Zn1—O3—S3A | 139.8 (3) | C8—C9—C10—C7 | 1.3 (5) |
N2—Zn1—O3—S3A | −40.7 (3) | C8—C9—C10—C11 | 179.6 (4) |
O4—Zn1—O3—S3A | −143.4 (3) | C15—O5—C13—C14 | −1.5 (7) |
O1—Zn1—O3—S3A | 39.0 (3) | O5—C13—C14—C12 | 1.3 (8) |
O3—Zn1—O4—C16 | −109.3 (2) | C15—C12—C14—C13 | −0.5 (7) |
N4—Zn1—O4—C16 | 6.6 (2) | C14—C12—C15—O5 | −0.3 (5) |
N2—Zn1—O4—C16 | 132.1 (2) | C14—C12—C15—C16 | 179.9 (4) |
O1—Zn1—O4—C16 | 50.9 (8) | C13—O5—C15—C12 | 1.1 (5) |
C5—N1—N2—C6 | −177.7 (3) | C13—O5—C15—C16 | −179.1 (4) |
C5—N1—N2—Zn1 | −1.1 (4) | N3—N4—C17—C18 | −2.4 (5) |
O3—Zn1—N2—C6 | −91.3 (3) | Zn1—N4—C17—C18 | 174.6 (3) |
N4—Zn1—N2—C6 | 88.1 (3) | N4—C17—C18—C21 | −174.2 (4) |
O4—Zn1—N2—C6 | 4.7 (3) | N4—C17—C18—S2 | 1.9 (5) |
O1—Zn1—N2—C6 | 177.7 (3) | C19—S2—C18—C21 | −1.3 (3) |
O3—Zn1—N2—N1 | 92.6 (2) | C19—S2—C18—C17 | −177.8 (3) |
N4—Zn1—N2—N1 | −87.9 (2) | C18—S2—C19—C20 | 0.8 (4) |
O4—Zn1—N2—N1 | −171.4 (2) | S2—C19—C20—C21 | −0.1 (6) |
O1—Zn1—N2—N1 | 1.7 (2) | C17—C18—C21—C20 | 178.0 (3) |
C16—N3—N4—C17 | −176.2 (3) | S2—C18—C21—C20 | 1.4 (4) |
C16—N3—N4—Zn1 | 6.4 (3) | C17—C18—C21—C22 | −5.7 (6) |
O3—Zn1—N4—C17 | −100.0 (3) | S2—C18—C21—C22 | 177.7 (4) |
N2—Zn1—N4—C17 | 80.5 (3) | C19—C20—C21—C18 | −0.8 (6) |
O4—Zn1—N4—C17 | 175.7 (3) | C19—C20—C21—C22 | −177.1 (5) |
O1—Zn1—N4—C17 | 0.5 (3) | O3—S3A—C23—S3B | 34.2 (19) |
O3—Zn1—N4—N3 | 77.0 (2) | C24—S3A—C23—S3B | −73.9 (19) |
N2—Zn1—N4—N3 | −102.5 (2) | O3—S3B—C23—S3A | −71.9 (18) |
O4—Zn1—N4—N3 | −7.3 (2) | C24—S3B—C23—S3A | 65.5 (11) |
O1—Zn1—N4—N3 | 177.6 (2) | O3—S3A—C24—S3B | −35.7 (12) |
C4—C1—C2—C3 | −0.1 (5) | C23—S3A—C24—S3B | 71.2 (12) |
C1—C2—C3—O2 | 0.1 (6) | O3—S3B—C24—S3A | 71 (2) |
C4—O2—C3—C2 | 0.0 (5) | C23—S3B—C24—S3A | −68.3 (10) |
C2—C1—C4—O2 | 0.1 (5) | Zn1—O4—C16—N3 | −5.8 (4) |
C2—C1—C4—C5 | 178.7 (4) | Zn1—O4—C16—C15 | 174.8 (2) |
C3—O2—C4—C1 | 0.0 (4) | N4—N3—C16—O4 | −0.2 (5) |
C3—O2—C4—C5 | −178.8 (3) | N4—N3—C16—C15 | 179.2 (3) |
Zn1—O1—C5—N1 | 2.1 (5) | C12—C15—C16—O4 | 176.4 (4) |
Zn1—O1—C5—C4 | −176.9 (2) | O5—C15—C16—O4 | −3.4 (5) |
N2—N1—C5—O1 | −0.7 (5) | C12—C15—C16—N3 | −3.1 (6) |
N2—N1—C5—C4 | 178.3 (3) | O5—C15—C16—N3 | 177.1 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O1i | 0.93 | 2.50 | 3.385 (5) | 159 |
C20—H20A···O4ii | 0.93 | 2.46 | 3.308 (5) | 152 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x−1, y, z. |