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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
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.052
- wR factor = 0.149
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.98
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.60 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C13 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C23 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... S3B PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... S3A PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C15 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 4 O4 -ZN1 -O1 -C5 80.70 0.80 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7 C23 -S3B -O3 -ZN1 104.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 C24 -S3B -O3 -ZN1 -22.00 11.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 13 N4 -ZN1 -O3 -S3B 105.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 14 N2 -ZN1 -O3 -S3B -76.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 15 O4 -ZN1 -O3 -S3B -178.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 O1 -ZN1 -O3 -S3B 4.00 9.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 24 O1 -ZN1 -O4 -C16 50.90 0.80 1.555 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.10 Deg. C23 -S3A -H23F 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 31.80 Deg. C24 -S3A -H24E 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 30.70 Deg. C23 -S3B -H23B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.40 Deg. S3A -C23 -S3B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.70 Deg. H23A -C23 -H23D 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 35.30 Deg. S3A -C24 -S3B 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 25.00 Deg. H24A -C24 -H24B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 24 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 9 ALERT type 4 Improvement, methodology, query or suggestion
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. |
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