In the title compound, [Zn(C
15H
10FN
2O
2 S)
2]·0.5H
2O, the Zn atom has a distorted tetrahedral geometry, formed by the N atoms of the quinoline and the sulfonamide groups. The water molecule occupies a special position on a twofold axis. Intermolecular C—H
O hydrogen bonds to the sulfonyl O atoms link the molecules into a three-dimensional network.
Supporting information
CCDC reference: 613603
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.007 Å
- H-atom completeness 96%
- R factor = 0.056
- wR factor = 0.143
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT306_ALERT_2_A Isolated Oxygen Atom (H-atoms Missing ?) ....... O5
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ?
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C25
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C28
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G
FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and the formula from the _atom_site* data.
Atom count from _chemical_formula_sum:C30 H21 F2 N4 O4.5 S2 Zn1
Atom count from the _atom_site data: C30 H20 F2 N4 O4.5 S2 Zn1
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
From the CIF: _cell_formula_units_Z 8
From the CIF: _chemical_formula_sum C30 H21 F2 N4 O4.50 S2 Zn
TEST: Compare cell contents of formula and atom_site data
atom Z*formula cif sites diff
C 240.00 240.00 0.00
H 168.00 160.00 8.00
F 16.00 16.00 0.00
N 32.00 32.00 0.00
O 36.00 36.00 0.00
S 16.00 16.00 0.00
Zn 8.00 8.00 0.00
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
9 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
6 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
Bis[4-fluoro-
N-(quinolin-8-yl)benzenesulfonamidato-
κ2N,
N']zinc(II) hemihydrate
top
Crystal data top
[Zn(C15H10FN2O2S)2]·0.5H2O | F(000) = 2760 |
Mr = 677.00 | Dx = 1.596 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2790 reflections |
a = 23.401 (1) Å | θ = 2.3–19.2° |
b = 16.843 (1) Å | µ = 1.08 mm−1 |
c = 17.186 (1) Å | T = 299 K |
β = 123.710 (1)° | Prism, light green |
V = 5634.8 (5) Å3 | 0.20 × 0.12 × 0.12 mm |
Z = 8 | |
Data collection top
Oxford Xcalibur Sapphire CCD area-detector diffractometer | 5667 independent reflections |
Radiation source: fine-focus sealed tube | 3364 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Rotation method data acquisition using ω and φ scans | θmax = 26.4°, θmin = 4.2° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2004) | h = −29→28 |
Tmin = 0.778, Tmax = 0.900 | k = −20→20 |
20017 measured reflections | l = −11→21 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0639P)2] where P = (Fo2 + 2Fc2)/3 |
5667 reflections | (Δ/σ)max = 0.003 |
393 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.27849 (2) | 0.22340 (3) | 0.26811 (3) | 0.0549 (2) | |
S1 | 0.31379 (7) | 0.40397 (7) | 0.30890 (8) | 0.0696 (4) | |
S2 | 0.42269 (6) | 0.14706 (6) | 0.35732 (8) | 0.0635 (3) | |
F1 | 0.54774 (16) | 0.4624 (2) | 0.6884 (2) | 0.1289 (12) | |
F2 | 0.43892 (15) | −0.19859 (16) | 0.3587 (2) | 0.0941 (9) | |
O1 | 0.27345 (17) | 0.47538 (18) | 0.2785 (2) | 0.0934 (11) | |
O2 | 0.3419 (2) | 0.3770 (2) | 0.2572 (2) | 0.1026 (13) | |
O3 | 0.41631 (16) | 0.17148 (17) | 0.4326 (2) | 0.0785 (9) | |
O4 | 0.47965 (15) | 0.17735 (18) | 0.3565 (2) | 0.0878 (10) | |
N1 | 0.27266 (18) | 0.32925 (18) | 0.3110 (2) | 0.0574 (9) | |
N2 | 0.22516 (16) | 0.19085 (18) | 0.3233 (2) | 0.0487 (8) | |
N3 | 0.35004 (16) | 0.16763 (19) | 0.2647 (2) | 0.0526 (8) | |
N4 | 0.22183 (16) | 0.19866 (16) | 0.1278 (2) | 0.0427 (7) | |
C1 | 0.2341 (2) | 0.3308 (2) | 0.3508 (3) | 0.0493 (10) | |
C2 | 0.2165 (2) | 0.3950 (3) | 0.3820 (3) | 0.0662 (12) | |
H2 | 0.2308 | 0.4454 | 0.3780 | 0.079* | |
C3 | 0.1766 (2) | 0.3854 (3) | 0.4203 (3) | 0.0742 (13) | |
H3 | 0.1657 | 0.4300 | 0.4415 | 0.089* | |
C4 | 0.1541 (2) | 0.3139 (3) | 0.4269 (3) | 0.0717 (13) | |
H4 | 0.1284 | 0.3095 | 0.4529 | 0.086* | |
C5 | 0.1694 (2) | 0.2456 (3) | 0.3947 (3) | 0.0557 (10) | |
C6 | 0.1483 (2) | 0.1683 (3) | 0.3981 (3) | 0.0648 (12) | |
H6 | 0.1226 | 0.1598 | 0.4235 | 0.078* | |
C7 | 0.1649 (2) | 0.1072 (3) | 0.3651 (3) | 0.0703 (13) | |
H7 | 0.1509 | 0.0561 | 0.3676 | 0.084* | |
C8 | 0.2034 (2) | 0.1200 (2) | 0.3270 (3) | 0.0612 (11) | |
H8 | 0.2140 | 0.0769 | 0.3033 | 0.073* | |
C9 | 0.20969 (19) | 0.2551 (2) | 0.3568 (2) | 0.0482 (9) | |
C10 | 0.3839 (2) | 0.4218 (2) | 0.4238 (3) | 0.0512 (10) | |
C11 | 0.3866 (2) | 0.4880 (2) | 0.4721 (3) | 0.0641 (12) | |
H11 | 0.3504 | 0.5240 | 0.4443 | 0.077* | |
C12 | 0.4420 (3) | 0.5015 (3) | 0.5607 (3) | 0.0740 (13) | |
H12 | 0.4442 | 0.5470 | 0.5928 | 0.089* | |
C13 | 0.4932 (3) | 0.4484 (3) | 0.6008 (4) | 0.0777 (14) | |
C14 | 0.4928 (3) | 0.3817 (3) | 0.5572 (4) | 0.0850 (15) | |
H14 | 0.5291 | 0.3460 | 0.5871 | 0.102* | |
C15 | 0.4370 (3) | 0.3674 (3) | 0.4664 (4) | 0.0726 (13) | |
H15 | 0.4355 | 0.3218 | 0.4348 | 0.087* | |
C16 | 0.3326 (2) | 0.1495 (2) | 0.1750 (3) | 0.0484 (10) | |
C17 | 0.3735 (2) | 0.1193 (3) | 0.1484 (3) | 0.0643 (12) | |
H17 | 0.4197 | 0.1101 | 0.1935 | 0.077* | |
C18 | 0.3475 (3) | 0.1019 (2) | 0.0551 (4) | 0.0702 (13) | |
H18 | 0.3771 | 0.0817 | 0.0398 | 0.084* | |
C19 | 0.2806 (3) | 0.1134 (2) | −0.0139 (3) | 0.0626 (12) | |
H19 | 0.2644 | 0.0992 | −0.0751 | 0.075* | |
C20 | 0.2357 (2) | 0.1473 (2) | 0.0074 (3) | 0.0462 (9) | |
C21 | 0.1674 (2) | 0.1659 (2) | −0.0588 (3) | 0.0568 (11) | |
H21 | 0.1485 | 0.1552 | −0.1216 | 0.068* | |
C22 | 0.1278 (2) | 0.1996 (2) | −0.0324 (3) | 0.0587 (11) | |
H22 | 0.0821 | 0.2121 | −0.0765 | 0.070* | |
C23 | 0.1575 (2) | 0.2149 (2) | 0.0620 (3) | 0.0514 (10) | |
H23 | 0.1303 | 0.2380 | 0.0798 | 0.062* | |
C24 | 0.26235 (19) | 0.16466 (19) | 0.1020 (3) | 0.0422 (9) | |
C25 | 0.43029 (19) | 0.0425 (2) | 0.3606 (3) | 0.0526 (10) | |
C26 | 0.4779 (2) | 0.0051 (3) | 0.3503 (4) | 0.0804 (15) | |
H26 | 0.5080 | 0.0351 | 0.3430 | 0.097* | |
C27 | 0.4810 (2) | −0.0767 (3) | 0.3507 (4) | 0.0812 (15) | |
H27 | 0.5133 | −0.1026 | 0.3443 | 0.097* | |
C28 | 0.4363 (2) | −0.1179 (3) | 0.3604 (3) | 0.0619 (11) | |
C29 | 0.3890 (2) | −0.0838 (3) | 0.3702 (3) | 0.0728 (13) | |
H29 | 0.3587 | −0.1147 | 0.3762 | 0.087* | |
C30 | 0.3859 (2) | −0.0031 (3) | 0.3713 (3) | 0.0680 (12) | |
H30 | 0.3539 | 0.0214 | 0.3793 | 0.082* | |
O5 | 0.5000 | 0.3306 (11) | 0.2500 | 0.556 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0616 (4) | 0.0613 (3) | 0.0510 (3) | −0.0077 (2) | 0.0370 (3) | −0.0051 (2) |
S1 | 0.0867 (9) | 0.0667 (8) | 0.0540 (7) | −0.0274 (6) | 0.0382 (7) | 0.0006 (6) |
S2 | 0.0515 (7) | 0.0607 (7) | 0.0609 (7) | −0.0058 (5) | 0.0204 (6) | 0.0107 (6) |
F1 | 0.086 (2) | 0.127 (3) | 0.092 (2) | −0.010 (2) | −0.0009 (19) | 0.008 (2) |
F2 | 0.112 (2) | 0.0643 (17) | 0.106 (2) | 0.0082 (15) | 0.061 (2) | 0.0086 (15) |
O1 | 0.092 (2) | 0.068 (2) | 0.069 (2) | −0.0163 (18) | 0.0133 (19) | 0.0275 (17) |
O2 | 0.146 (3) | 0.122 (3) | 0.079 (2) | −0.065 (2) | 0.087 (3) | −0.028 (2) |
O3 | 0.092 (2) | 0.071 (2) | 0.0509 (19) | −0.0015 (17) | 0.0261 (18) | 0.0004 (15) |
O4 | 0.055 (2) | 0.073 (2) | 0.117 (3) | −0.0117 (16) | 0.037 (2) | 0.0198 (19) |
N1 | 0.071 (2) | 0.053 (2) | 0.059 (2) | −0.0204 (17) | 0.042 (2) | −0.0088 (16) |
N2 | 0.058 (2) | 0.0483 (19) | 0.0450 (19) | −0.0076 (16) | 0.0319 (18) | −0.0021 (15) |
N3 | 0.047 (2) | 0.067 (2) | 0.043 (2) | 0.0040 (16) | 0.0250 (17) | 0.0068 (16) |
N4 | 0.0448 (19) | 0.0393 (16) | 0.0491 (19) | 0.0014 (14) | 0.0293 (17) | −0.0005 (14) |
C1 | 0.055 (3) | 0.046 (2) | 0.041 (2) | −0.0017 (19) | 0.023 (2) | −0.0035 (18) |
C2 | 0.072 (3) | 0.059 (3) | 0.063 (3) | −0.001 (2) | 0.035 (3) | −0.003 (2) |
C3 | 0.075 (3) | 0.081 (4) | 0.068 (3) | 0.021 (3) | 0.041 (3) | −0.009 (3) |
C4 | 0.060 (3) | 0.099 (4) | 0.064 (3) | 0.005 (3) | 0.039 (3) | −0.003 (3) |
C5 | 0.045 (2) | 0.082 (3) | 0.040 (2) | 0.001 (2) | 0.023 (2) | −0.003 (2) |
C6 | 0.058 (3) | 0.088 (3) | 0.059 (3) | −0.016 (2) | 0.040 (2) | 0.003 (2) |
C7 | 0.087 (4) | 0.067 (3) | 0.066 (3) | −0.023 (3) | 0.048 (3) | −0.008 (2) |
C8 | 0.076 (3) | 0.056 (3) | 0.060 (3) | −0.014 (2) | 0.043 (3) | −0.008 (2) |
C9 | 0.048 (2) | 0.056 (2) | 0.036 (2) | −0.0037 (19) | 0.021 (2) | −0.0009 (19) |
C10 | 0.055 (3) | 0.043 (2) | 0.060 (3) | −0.0092 (19) | 0.035 (2) | 0.004 (2) |
C11 | 0.065 (3) | 0.043 (2) | 0.068 (3) | 0.003 (2) | 0.027 (3) | 0.006 (2) |
C12 | 0.076 (3) | 0.064 (3) | 0.063 (3) | −0.009 (3) | 0.027 (3) | −0.009 (2) |
C13 | 0.055 (3) | 0.076 (3) | 0.079 (4) | −0.007 (3) | 0.022 (3) | 0.014 (3) |
C14 | 0.063 (3) | 0.064 (3) | 0.123 (5) | 0.007 (3) | 0.049 (4) | 0.011 (3) |
C15 | 0.073 (3) | 0.055 (3) | 0.105 (4) | −0.003 (2) | 0.059 (3) | −0.007 (3) |
C16 | 0.051 (3) | 0.046 (2) | 0.058 (3) | 0.0072 (18) | 0.037 (2) | 0.0158 (19) |
C17 | 0.059 (3) | 0.083 (3) | 0.066 (3) | 0.023 (2) | 0.045 (3) | 0.030 (2) |
C18 | 0.083 (4) | 0.070 (3) | 0.086 (4) | 0.023 (3) | 0.065 (3) | 0.020 (3) |
C19 | 0.093 (4) | 0.056 (3) | 0.064 (3) | 0.003 (2) | 0.060 (3) | 0.002 (2) |
C20 | 0.058 (3) | 0.040 (2) | 0.051 (2) | 0.0005 (18) | 0.036 (2) | 0.0024 (18) |
C21 | 0.064 (3) | 0.057 (3) | 0.048 (2) | −0.006 (2) | 0.030 (2) | −0.001 (2) |
C22 | 0.053 (3) | 0.059 (3) | 0.058 (3) | 0.000 (2) | 0.027 (2) | 0.000 (2) |
C23 | 0.055 (3) | 0.046 (2) | 0.066 (3) | 0.0003 (19) | 0.041 (2) | −0.003 (2) |
C24 | 0.054 (2) | 0.0349 (19) | 0.052 (2) | 0.0017 (17) | 0.038 (2) | 0.0047 (17) |
C25 | 0.039 (2) | 0.059 (2) | 0.047 (2) | −0.0023 (19) | 0.016 (2) | 0.0133 (19) |
C26 | 0.053 (3) | 0.081 (3) | 0.112 (4) | 0.006 (2) | 0.048 (3) | 0.032 (3) |
C27 | 0.064 (3) | 0.074 (3) | 0.115 (4) | 0.024 (3) | 0.056 (3) | 0.030 (3) |
C28 | 0.068 (3) | 0.055 (3) | 0.060 (3) | 0.004 (2) | 0.033 (3) | 0.012 (2) |
C29 | 0.088 (4) | 0.060 (3) | 0.096 (4) | −0.009 (3) | 0.067 (3) | 0.004 (3) |
C30 | 0.072 (3) | 0.066 (3) | 0.081 (3) | −0.004 (2) | 0.052 (3) | 0.008 (2) |
O5 | 0.44 (2) | 0.43 (2) | 0.261 (17) | 0.000 | −0.135 (18) | 0.000 |
Geometric parameters (Å, º) top
Zn1—N3 | 1.949 (3) | C8—H8 | 0.9300 |
Zn1—N1 | 1.963 (3) | C10—C11 | 1.370 (5) |
Zn1—N2 | 2.018 (3) | C10—C15 | 1.382 (6) |
Zn1—N4 | 2.049 (3) | C11—C12 | 1.363 (6) |
Zn1—O3 | 3.006 (3) | C11—H11 | 0.9300 |
Zn1—O2 | 3.039 (3) | C12—C13 | 1.339 (6) |
S1—O1 | 1.436 (3) | C12—H12 | 0.9300 |
S1—O2 | 1.441 (3) | C13—C14 | 1.347 (6) |
S1—N1 | 1.597 (3) | C14—C15 | 1.390 (6) |
S1—C10 | 1.756 (4) | C14—H14 | 0.9300 |
S2—O4 | 1.435 (3) | C15—H15 | 0.9300 |
S2—O3 | 1.441 (3) | C16—C17 | 1.368 (5) |
S2—N3 | 1.594 (3) | C16—C24 | 1.433 (5) |
S2—C25 | 1.768 (4) | C17—C18 | 1.394 (6) |
F1—C13 | 1.348 (5) | C17—H17 | 0.9300 |
F2—C28 | 1.361 (5) | C18—C19 | 1.354 (6) |
N1—C1 | 1.404 (5) | C18—H18 | 0.9300 |
N2—C8 | 1.313 (5) | C19—C20 | 1.413 (5) |
N2—C9 | 1.365 (5) | C19—H19 | 0.9300 |
N3—C16 | 1.392 (5) | C20—C21 | 1.389 (5) |
N4—C23 | 1.315 (5) | C20—C24 | 1.411 (5) |
N4—C24 | 1.375 (4) | C21—C22 | 1.360 (5) |
C1—C2 | 1.366 (5) | C21—H21 | 0.9300 |
C1—C9 | 1.423 (5) | C22—C23 | 1.390 (5) |
C2—C3 | 1.420 (6) | C22—H22 | 0.9300 |
C2—H2 | 0.9300 | C23—H23 | 0.9300 |
C3—C4 | 1.345 (6) | C25—C26 | 1.374 (6) |
C3—H3 | 0.9300 | C25—C30 | 1.384 (5) |
C4—C5 | 1.406 (6) | C26—C27 | 1.380 (6) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.405 (6) | C27—C28 | 1.342 (6) |
C5—C9 | 1.422 (5) | C27—H27 | 0.9300 |
C6—C7 | 1.333 (6) | C28—C29 | 1.338 (6) |
C6—H6 | 0.9300 | C29—C30 | 1.361 (6) |
C7—C8 | 1.394 (5) | C29—H29 | 0.9300 |
C7—H7 | 0.9300 | C30—H30 | 0.9300 |
| | | |
N3—Zn1—N1 | 133.55 (14) | N2—C9—C1 | 118.0 (3) |
N3—Zn1—N2 | 130.46 (13) | C5—C9—C1 | 121.9 (4) |
N1—Zn1—N2 | 83.12 (13) | C11—C10—C15 | 119.5 (4) |
N3—Zn1—N4 | 82.66 (12) | C11—C10—S1 | 121.4 (3) |
N1—Zn1—N4 | 119.49 (13) | C15—C10—S1 | 119.1 (3) |
N2—Zn1—N4 | 109.46 (12) | C12—C11—C10 | 120.5 (4) |
N3—Zn1—O3 | 52.89 (11) | C12—C11—H11 | 119.7 |
N1—Zn1—O3 | 99.97 (12) | C10—C11—H11 | 119.7 |
N2—Zn1—O3 | 95.72 (11) | C13—C12—C11 | 119.3 (5) |
N4—Zn1—O3 | 134.69 (10) | C13—C12—H12 | 120.4 |
N3—Zn1—O2 | 87.23 (12) | C11—C12—H12 | 120.4 |
N1—Zn1—O2 | 52.25 (11) | C12—C13—C14 | 122.7 (5) |
N2—Zn1—O2 | 135.27 (11) | C12—C13—F1 | 118.7 (5) |
N4—Zn1—O2 | 96.87 (10) | C14—C13—F1 | 118.6 (5) |
O3—Zn1—O2 | 90.00 (10) | C13—C14—C15 | 118.8 (5) |
O1—S1—O2 | 118.2 (2) | C13—C14—H14 | 120.6 |
O1—S1—N1 | 112.7 (2) | C15—C14—H14 | 120.6 |
O2—S1—N1 | 104.59 (18) | C10—C15—C14 | 119.2 (4) |
O1—S1—C10 | 106.31 (19) | C10—C15—H15 | 120.4 |
O2—S1—C10 | 106.6 (2) | C14—C15—H15 | 120.4 |
N1—S1—C10 | 107.93 (17) | C17—C16—N3 | 128.5 (4) |
O4—S2—O3 | 117.8 (2) | C17—C16—C24 | 116.7 (4) |
O4—S2—N3 | 113.24 (18) | N3—C16—C24 | 114.8 (3) |
O3—S2—N3 | 104.45 (18) | C16—C17—C18 | 121.6 (4) |
O4—S2—C25 | 106.08 (19) | C16—C17—H17 | 119.2 |
O3—S2—C25 | 108.31 (19) | C18—C17—H17 | 119.2 |
N3—S2—C25 | 106.33 (18) | C19—C18—C17 | 122.1 (4) |
S1—O2—Zn1 | 79.95 (13) | C19—C18—H18 | 119.0 |
S2—O3—Zn1 | 80.26 (13) | C17—C18—H18 | 119.0 |
C1—N1—S1 | 123.7 (3) | C18—C19—C20 | 119.8 (4) |
C1—N1—Zn1 | 113.4 (2) | C18—C19—H19 | 120.1 |
S1—N1—Zn1 | 122.63 (19) | C20—C19—H19 | 120.1 |
C8—N2—C9 | 120.0 (3) | C21—C20—C24 | 118.0 (3) |
C8—N2—Zn1 | 128.8 (3) | C21—C20—C19 | 124.3 (4) |
C9—N2—Zn1 | 111.1 (2) | C24—C20—C19 | 117.8 (4) |
C16—N3—S2 | 123.5 (3) | C22—C21—C20 | 120.5 (4) |
C16—N3—Zn1 | 114.2 (2) | C22—C21—H21 | 119.7 |
S2—N3—Zn1 | 122.21 (18) | C20—C21—H21 | 119.7 |
C23—N4—C24 | 118.3 (3) | C21—C22—C23 | 118.4 (4) |
C23—N4—Zn1 | 130.8 (3) | C21—C22—H22 | 120.8 |
C24—N4—Zn1 | 110.6 (2) | C23—C22—H22 | 120.8 |
C2—C1—N1 | 128.3 (4) | N4—C23—C22 | 123.8 (4) |
C2—C1—C9 | 117.4 (4) | N4—C23—H23 | 118.1 |
N1—C1—C9 | 114.2 (3) | C22—C23—H23 | 118.1 |
C1—C2—C3 | 120.7 (4) | N4—C24—C20 | 121.0 (3) |
C1—C2—H2 | 119.7 | N4—C24—C16 | 117.0 (3) |
C3—C2—H2 | 119.7 | C20—C24—C16 | 122.1 (3) |
C4—C3—C2 | 122.0 (4) | C26—C25—C30 | 119.0 (4) |
C4—C3—H3 | 119.0 | C26—C25—S2 | 121.8 (3) |
C2—C3—H3 | 119.0 | C30—C25—S2 | 119.2 (3) |
C3—C4—C5 | 120.1 (4) | C25—C26—C27 | 120.1 (4) |
C3—C4—H4 | 119.9 | C25—C26—H26 | 119.9 |
C5—C4—H4 | 119.9 | C27—C26—H26 | 119.9 |
C6—C5—C4 | 124.7 (4) | C28—C27—C26 | 118.3 (4) |
C6—C5—C9 | 117.4 (4) | C28—C27—H27 | 120.8 |
C4—C5—C9 | 117.8 (4) | C26—C27—H27 | 120.8 |
C7—C6—C5 | 120.4 (4) | C29—C28—C27 | 123.3 (4) |
C7—C6—H6 | 119.8 | C29—C28—F2 | 118.8 (4) |
C5—C6—H6 | 119.8 | C27—C28—F2 | 117.8 (4) |
C6—C7—C8 | 119.8 (4) | C28—C29—C30 | 119.1 (4) |
C6—C7—H7 | 120.1 | C28—C29—H29 | 120.5 |
C8—C7—H7 | 120.1 | C30—C29—H29 | 120.5 |
N2—C8—C7 | 122.1 (4) | C29—C30—C25 | 120.2 (4) |
N2—C8—H8 | 118.9 | C29—C30—H30 | 119.9 |
C7—C8—H8 | 118.9 | C25—C30—H30 | 119.9 |
N2—C9—C5 | 120.1 (4) | | |
| | | |
O1—S1—O2—Zn1 | −131.33 (17) | C4—C5—C6—C7 | 179.5 (4) |
N1—S1—O2—Zn1 | −5.06 (17) | C9—C5—C6—C7 | −1.2 (6) |
C10—S1—O2—Zn1 | 109.13 (14) | C5—C6—C7—C8 | −0.1 (7) |
N3—Zn1—O2—S1 | −150.45 (18) | C9—N2—C8—C7 | −0.6 (6) |
N1—Zn1—O2—S1 | 5.03 (17) | Zn1—N2—C8—C7 | −177.9 (3) |
N2—Zn1—O2—S1 | 0.5 (3) | C6—C7—C8—N2 | 1.0 (7) |
N4—Zn1—O2—S1 | 127.29 (17) | C8—N2—C9—C5 | −0.7 (5) |
O3—Zn1—O2—S1 | −97.61 (17) | Zn1—N2—C9—C5 | 177.0 (3) |
O4—S2—O3—Zn1 | 123.73 (17) | C8—N2—C9—C1 | −179.6 (4) |
N3—S2—O3—Zn1 | −2.92 (14) | Zn1—N2—C9—C1 | −1.9 (4) |
C25—S2—O3—Zn1 | −115.95 (14) | C6—C5—C9—N2 | 1.5 (5) |
N3—Zn1—O3—S2 | 2.90 (14) | C4—C5—C9—N2 | −179.1 (4) |
N1—Zn1—O3—S2 | −135.19 (14) | C6—C5—C9—C1 | −179.6 (4) |
N2—Zn1—O3—S2 | 140.81 (15) | C4—C5—C9—C1 | −0.2 (6) |
N4—Zn1—O3—S2 | 16.1 (2) | C2—C1—C9—N2 | 178.1 (4) |
O2—Zn1—O3—S2 | −83.62 (13) | N1—C1—C9—N2 | −0.7 (5) |
O1—S1—N1—C1 | −47.0 (4) | C2—C1—C9—C5 | −0.9 (6) |
O2—S1—N1—C1 | −176.7 (3) | N1—C1—C9—C5 | −179.6 (3) |
C10—S1—N1—C1 | 70.1 (4) | O1—S1—C10—C11 | 9.9 (4) |
O1—S1—N1—Zn1 | 138.8 (2) | O2—S1—C10—C11 | 136.9 (3) |
O2—S1—N1—Zn1 | 9.2 (3) | N1—S1—C10—C11 | −111.2 (3) |
C10—S1—N1—Zn1 | −104.1 (2) | O1—S1—C10—C15 | −170.6 (3) |
N3—Zn1—N1—C1 | −145.1 (2) | O2—S1—C10—C15 | −43.7 (4) |
N2—Zn1—N1—C1 | −3.2 (3) | N1—S1—C10—C15 | 68.2 (4) |
N4—Zn1—N1—C1 | 105.3 (3) | C15—C10—C11—C12 | 1.7 (6) |
O3—Zn1—N1—C1 | −97.8 (3) | S1—C10—C11—C12 | −178.9 (3) |
O2—Zn1—N1—C1 | 180.0 (3) | C10—C11—C12—C13 | −1.4 (7) |
N3—Zn1—N1—S1 | 29.6 (3) | C11—C12—C13—C14 | 0.4 (8) |
N2—Zn1—N1—S1 | 171.5 (2) | C11—C12—C13—F1 | 179.9 (4) |
N4—Zn1—N1—S1 | −80.0 (3) | C12—C13—C14—C15 | 0.3 (8) |
O3—Zn1—N1—S1 | 76.9 (2) | F1—C13—C14—C15 | −179.3 (4) |
O2—Zn1—N1—S1 | −5.31 (17) | C11—C10—C15—C14 | −1.0 (6) |
N3—Zn1—N2—C8 | −35.8 (4) | S1—C10—C15—C14 | 179.5 (3) |
N1—Zn1—N2—C8 | −179.8 (4) | C13—C14—C15—C10 | 0.0 (7) |
N4—Zn1—N2—C8 | 61.3 (4) | S2—N3—C16—C17 | −6.7 (6) |
O3—Zn1—N2—C8 | −80.4 (3) | Zn1—N3—C16—C17 | 171.8 (3) |
O2—Zn1—N2—C8 | −176.2 (3) | S2—N3—C16—C24 | 173.2 (2) |
N3—Zn1—N2—C9 | 146.8 (2) | Zn1—N3—C16—C24 | −8.4 (4) |
N1—Zn1—N2—C9 | 2.8 (2) | N3—C16—C17—C18 | 177.9 (4) |
N4—Zn1—N2—C9 | −116.1 (2) | C24—C16—C17—C18 | −1.9 (6) |
O3—Zn1—N2—C9 | 102.2 (2) | C16—C17—C18—C19 | −0.3 (7) |
O2—Zn1—N2—C9 | 6.4 (3) | C17—C18—C19—C20 | 2.7 (6) |
O4—S2—N3—C16 | 54.2 (4) | C18—C19—C20—C21 | 176.0 (4) |
O3—S2—N3—C16 | −176.4 (3) | C18—C19—C20—C24 | −2.6 (5) |
C25—S2—N3—C16 | −61.9 (3) | C24—C20—C21—C22 | −0.2 (5) |
O4—S2—N3—Zn1 | −124.2 (2) | C19—C20—C21—C22 | −178.9 (4) |
O3—S2—N3—Zn1 | 5.3 (3) | C20—C21—C22—C23 | 0.1 (6) |
C25—S2—N3—Zn1 | 119.7 (2) | C24—N4—C23—C22 | 0.1 (5) |
N1—Zn1—N3—C16 | −116.4 (3) | Zn1—N4—C23—C22 | 174.5 (3) |
N2—Zn1—N3—C16 | 117.2 (3) | C21—C22—C23—N4 | 0.0 (6) |
N4—Zn1—N3—C16 | 7.8 (2) | C23—N4—C24—C20 | −0.3 (5) |
O3—Zn1—N3—C16 | 178.4 (3) | Zn1—N4—C24—C20 | −175.7 (3) |
O2—Zn1—N3—C16 | −89.5 (3) | C23—N4—C24—C16 | 178.5 (3) |
N1—Zn1—N3—S2 | 62.1 (3) | Zn1—N4—C24—C16 | 3.1 (4) |
N2—Zn1—N3—S2 | −64.3 (3) | C21—C20—C24—N4 | 0.3 (5) |
N4—Zn1—N3—S2 | −173.7 (2) | C19—C20—C24—N4 | 179.1 (3) |
O3—Zn1—N3—S2 | −3.06 (15) | C21—C20—C24—C16 | −178.4 (3) |
O2—Zn1—N3—S2 | 89.0 (2) | C19—C20—C24—C16 | 0.4 (5) |
N3—Zn1—N4—C23 | 179.4 (3) | C17—C16—C24—N4 | −176.9 (3) |
N1—Zn1—N4—C23 | −44.1 (3) | N3—C16—C24—N4 | 3.3 (5) |
N2—Zn1—N4—C23 | 49.0 (3) | C17—C16—C24—C20 | 1.9 (5) |
O3—Zn1—N4—C23 | 168.9 (3) | N3—C16—C24—C20 | −178.0 (3) |
O2—Zn1—N4—C23 | −94.3 (3) | O4—S2—C25—C26 | −8.2 (4) |
N3—Zn1—N4—C24 | −5.9 (2) | O3—S2—C25—C26 | −135.6 (4) |
N1—Zn1—N4—C24 | 130.6 (2) | N3—S2—C25—C26 | 112.7 (4) |
N2—Zn1—N4—C24 | −136.3 (2) | O4—S2—C25—C30 | 173.6 (3) |
O3—Zn1—N4—C24 | −16.4 (3) | O3—S2—C25—C30 | 46.2 (4) |
O2—Zn1—N4—C24 | 80.4 (2) | N3—S2—C25—C30 | −65.5 (4) |
S1—N1—C1—C2 | 9.8 (6) | C30—C25—C26—C27 | 0.0 (7) |
Zn1—N1—C1—C2 | −175.6 (3) | S2—C25—C26—C27 | −178.2 (4) |
S1—N1—C1—C9 | −171.6 (3) | C25—C26—C27—C28 | 0.7 (8) |
Zn1—N1—C1—C9 | 3.1 (4) | C26—C27—C28—C29 | −0.4 (7) |
N1—C1—C2—C3 | 179.8 (4) | C26—C27—C28—F2 | 178.7 (4) |
C9—C1—C2—C3 | 1.2 (6) | C27—C28—C29—C30 | −0.6 (7) |
C1—C2—C3—C4 | −0.6 (7) | F2—C28—C29—C30 | −179.6 (4) |
C2—C3—C4—C5 | −0.5 (7) | C28—C29—C30—C25 | 1.2 (7) |
C3—C4—C5—C6 | −179.8 (4) | C26—C25—C30—C29 | −1.0 (7) |
C3—C4—C5—C9 | 0.9 (6) | S2—C25—C30—C29 | 177.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.93 | 2.33 | 3.256 (5) | 171 |
C21—H21···O2ii | 0.93 | 2.52 | 3.373 (5) | 153 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z. |