Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620004994/qf3037sup1.cif | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620004994/qf3037sup2.pdf | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004994/qf3037shelxsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004994/qf3037shelx_1sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620004994/qf3037shelx_2sup5.hkl |
CCDC references: 1945859; 1944731; 1955626
For all structures, data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).
C20H18F2N4O2·CH4O | Dx = 1.367 Mg m−3 |
Mr = 416.42 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 13218 reflections |
a = 7.5679 (3) Å | θ = 1.8–31.0° |
b = 15.2500 (7) Å | µ = 0.11 mm−1 |
c = 17.5264 (7) Å | T = 296 K |
V = 2022.73 (15) Å3 | Prism, yellow |
Z = 4 | 0.79 × 0.55 × 0.38 mm |
F(000) = 872 |
Stoe IPDS 2 diffractometer | 6161 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3553 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.042 |
Detector resolution: 6.67 pixels mm-1 | θmax = 30.6°, θmin = 1.8° |
rotation method scans | h = −10→10 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −21→21 |
Tmin = 0.926, Tmax = 0.962 | l = −24→23 |
15870 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0509P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.111 | (Δ/σ)max < 0.001 |
S = 0.96 | Δρmax = 0.13 e Å−3 |
6161 reflections | Δρmin = −0.11 e Å−3 |
284 parameters | Absolute structure: Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.3 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of LF, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite. Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997). |
x | y | z | Uiso*/Ueq | ||
F1 | 0.4528 (3) | 1.10675 (12) | 0.60787 (11) | 0.1035 (7) | |
F2 | 0.2132 (3) | 0.39921 (15) | 0.70516 (9) | 0.0940 (6) | |
O1 | 0.5341 (4) | 0.70430 (13) | 0.53813 (10) | 0.0830 (7) | |
O2 | 0.4777 (4) | 0.36341 (13) | 0.36771 (10) | 0.0892 (8) | |
O3 | 0.5958 (3) | 0.37338 (14) | 0.20009 (11) | 0.0703 (6) | |
C21 | 0.7497 (6) | 0.3294 (3) | 0.2170 (2) | 0.0987 (12) | |
H21A | 0.827747 | 0.367562 | 0.244577 | 0.148* | |
H21B | 0.805659 | 0.310958 | 0.170523 | 0.148* | |
H21C | 0.723055 | 0.278930 | 0.247671 | 0.148* | |
N2 | 0.5744 (3) | 0.67763 (13) | 0.38715 (11) | 0.0534 (5) | |
N3 | 0.5911 (3) | 0.51341 (12) | 0.30988 (10) | 0.0498 (5) | |
N4 | 0.5234 (3) | 0.50838 (14) | 0.38164 (11) | 0.0506 (5) | |
N1 | 0.5658 (3) | 0.75956 (15) | 0.41977 (12) | 0.0583 (6) | |
C4 | 0.5121 (3) | 0.85858 (16) | 0.52371 (12) | 0.0513 (6) | |
C13 | 0.6506 (3) | 0.58657 (16) | 0.28352 (12) | 0.0492 (5) | |
C7 | 0.5350 (4) | 0.76724 (16) | 0.49571 (14) | 0.0551 (6) | |
C20 | 0.4054 (4) | 0.49610 (18) | 0.53713 (14) | 0.0596 (7) | |
H20 | 0.451810 | 0.549547 | 0.521260 | 0.071* | |
C15 | 0.4015 (3) | 0.42542 (17) | 0.48752 (13) | 0.0523 (6) | |
C14 | 0.4700 (4) | 0.42869 (17) | 0.40741 (13) | 0.0556 (6) | |
C12 | 0.7263 (4) | 0.57862 (19) | 0.20362 (15) | 0.0668 (7) | |
H12A | 0.838595 | 0.548106 | 0.206539 | 0.080* | |
H12B | 0.647050 | 0.543028 | 0.173088 | 0.080* | |
C3 | 0.4258 (4) | 0.92197 (18) | 0.48190 (14) | 0.0595 (6) | |
H3 | 0.380437 | 0.908133 | 0.434073 | 0.071* | |
C8 | 0.6539 (3) | 0.67224 (16) | 0.32176 (13) | 0.0497 (5) | |
C1 | 0.4732 (4) | 1.02404 (19) | 0.58029 (16) | 0.0663 (8) | |
C19 | 0.3397 (4) | 0.48679 (19) | 0.61068 (15) | 0.0654 (7) | |
H19 | 0.341261 | 0.533756 | 0.644520 | 0.078* | |
C6 | 0.5574 (4) | 0.9638 (2) | 0.62366 (15) | 0.0704 (8) | |
H6 | 0.601161 | 0.978450 | 0.671570 | 0.085* | |
C11 | 0.7544 (4) | 0.66483 (18) | 0.16377 (14) | 0.0637 (7) | |
H11A | 0.819733 | 0.655622 | 0.116840 | 0.076* | |
H11B | 0.641152 | 0.690762 | 0.150970 | 0.076* | |
C5 | 0.5766 (4) | 0.88046 (19) | 0.59531 (14) | 0.0647 (7) | |
H5 | 0.633697 | 0.838109 | 0.624468 | 0.078* | |
C16 | 0.3321 (4) | 0.34702 (19) | 0.51202 (15) | 0.0649 (7) | |
H16 | 0.329343 | 0.299550 | 0.478728 | 0.078* | |
C10 | 0.8552 (4) | 0.7251 (2) | 0.21512 (16) | 0.0691 (8) | |
H10A | 0.885119 | 0.778288 | 0.187610 | 0.083* | |
H10B | 0.964379 | 0.697093 | 0.230779 | 0.083* | |
C9 | 0.7468 (4) | 0.74831 (17) | 0.28522 (15) | 0.0630 (7) | |
H9A | 0.824373 | 0.774966 | 0.322699 | 0.076* | |
H9B | 0.659324 | 0.791780 | 0.270923 | 0.076* | |
C17 | 0.2660 (4) | 0.3372 (2) | 0.58539 (16) | 0.0702 (8) | |
H17 | 0.218584 | 0.284189 | 0.601711 | 0.084* | |
C18 | 0.2729 (4) | 0.4077 (2) | 0.63241 (14) | 0.0653 (7) | |
C2 | 0.4060 (4) | 1.00577 (18) | 0.51028 (16) | 0.0682 (7) | |
H2 | 0.347961 | 1.048702 | 0.482120 | 0.082* | |
H4 | 0.515 (4) | 0.5565 (19) | 0.4053 (15) | 0.059 (8)* | |
H1 | 0.569 (4) | 0.803 (2) | 0.3933 (19) | 0.080 (10)* | |
H3A | 0.574 (6) | 0.406 (3) | 0.234 (2) | 0.122 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.1378 (18) | 0.0714 (12) | 0.1011 (13) | −0.0034 (12) | 0.0141 (13) | −0.0412 (10) |
F2 | 0.1037 (13) | 0.1268 (16) | 0.0516 (9) | 0.0061 (12) | 0.0230 (9) | 0.0144 (10) |
O1 | 0.145 (2) | 0.0554 (12) | 0.0489 (10) | 0.0052 (13) | −0.0005 (12) | 0.0060 (8) |
O2 | 0.152 (2) | 0.0567 (12) | 0.0592 (11) | −0.0272 (13) | 0.0288 (13) | −0.0102 (9) |
O3 | 0.0958 (16) | 0.0657 (13) | 0.0496 (10) | −0.0005 (11) | −0.0034 (10) | −0.0111 (9) |
C21 | 0.123 (3) | 0.098 (3) | 0.075 (2) | 0.037 (2) | −0.008 (2) | −0.012 (2) |
N2 | 0.0699 (13) | 0.0449 (11) | 0.0453 (10) | 0.0021 (10) | 0.0058 (10) | −0.0019 (8) |
N3 | 0.0611 (12) | 0.0501 (12) | 0.0382 (9) | 0.0015 (10) | 0.0037 (9) | −0.0019 (8) |
N4 | 0.0652 (13) | 0.0467 (12) | 0.0400 (10) | −0.0027 (10) | 0.0052 (9) | 0.0000 (9) |
N1 | 0.0874 (17) | 0.0443 (12) | 0.0432 (11) | 0.0002 (11) | 0.0114 (11) | −0.0013 (9) |
C4 | 0.0609 (15) | 0.0526 (14) | 0.0404 (11) | −0.0041 (12) | 0.0061 (11) | −0.0019 (10) |
C13 | 0.0560 (13) | 0.0495 (14) | 0.0421 (12) | 0.0025 (11) | 0.0036 (10) | 0.0018 (10) |
C7 | 0.0673 (16) | 0.0516 (14) | 0.0463 (12) | −0.0006 (12) | 0.0034 (12) | 0.0002 (11) |
C20 | 0.0742 (17) | 0.0567 (16) | 0.0478 (12) | 0.0009 (13) | −0.0008 (12) | 0.0043 (11) |
C15 | 0.0595 (14) | 0.0529 (14) | 0.0444 (11) | −0.0034 (12) | −0.0008 (10) | 0.0048 (11) |
C14 | 0.0707 (16) | 0.0510 (14) | 0.0452 (11) | −0.0058 (13) | 0.0025 (11) | −0.0006 (11) |
C12 | 0.0879 (19) | 0.0629 (17) | 0.0496 (13) | −0.0047 (15) | 0.0183 (13) | −0.0026 (13) |
C3 | 0.0724 (17) | 0.0608 (16) | 0.0454 (12) | 0.0029 (15) | −0.0033 (12) | −0.0085 (12) |
C8 | 0.0557 (13) | 0.0491 (13) | 0.0443 (12) | 0.0010 (11) | 0.0041 (10) | 0.0032 (10) |
C1 | 0.0765 (19) | 0.0568 (16) | 0.0654 (16) | −0.0066 (14) | 0.0147 (15) | −0.0202 (13) |
C19 | 0.0798 (18) | 0.0705 (18) | 0.0458 (13) | 0.0121 (15) | 0.0026 (13) | −0.0028 (12) |
C6 | 0.085 (2) | 0.082 (2) | 0.0444 (13) | −0.0116 (17) | 0.0011 (14) | −0.0180 (13) |
C11 | 0.0787 (19) | 0.0659 (18) | 0.0464 (13) | −0.0048 (14) | 0.0112 (12) | 0.0069 (12) |
C5 | 0.0823 (19) | 0.0667 (17) | 0.0451 (13) | −0.0034 (14) | −0.0003 (13) | 0.0010 (12) |
C16 | 0.0820 (19) | 0.0598 (16) | 0.0530 (14) | −0.0093 (15) | 0.0041 (14) | 0.0031 (12) |
C10 | 0.0786 (18) | 0.0662 (17) | 0.0624 (16) | −0.0108 (15) | 0.0191 (15) | 0.0069 (14) |
C9 | 0.0788 (18) | 0.0500 (15) | 0.0604 (15) | −0.0069 (13) | 0.0175 (14) | −0.0002 (12) |
C17 | 0.078 (2) | 0.074 (2) | 0.0587 (15) | −0.0124 (16) | 0.0044 (14) | 0.0173 (15) |
C18 | 0.0642 (17) | 0.087 (2) | 0.0452 (13) | 0.0074 (15) | 0.0093 (12) | 0.0149 (14) |
C2 | 0.0851 (19) | 0.0600 (17) | 0.0594 (15) | 0.0106 (15) | 0.0028 (15) | −0.0081 (13) |
F1—C1 | 1.360 (3) | C12—C11 | 1.504 (4) |
F2—C18 | 1.359 (3) | C12—H12A | 0.9700 |
O1—C7 | 1.214 (3) | C12—H12B | 0.9700 |
O2—C14 | 1.216 (3) | C3—C2 | 1.379 (4) |
O3—C21 | 1.377 (4) | C3—H3 | 0.9300 |
O3—H3A | 0.79 (4) | C8—C9 | 1.500 (3) |
C21—H21A | 0.9600 | C1—C6 | 1.352 (4) |
C21—H21B | 0.9600 | C1—C2 | 1.357 (4) |
C21—H21C | 0.9600 | C19—C18 | 1.362 (4) |
N2—C8 | 1.297 (3) | C19—H19 | 0.9300 |
N2—N1 | 1.376 (3) | C6—C5 | 1.372 (4) |
N3—C13 | 1.289 (3) | C6—H6 | 0.9300 |
N3—N4 | 1.360 (3) | C11—C10 | 1.496 (4) |
N4—C14 | 1.358 (3) | C11—H11A | 0.9700 |
N4—H4 | 0.85 (3) | C11—H11B | 0.9700 |
N1—C7 | 1.356 (3) | C5—H5 | 0.9300 |
N1—H1 | 0.81 (3) | C16—C17 | 1.388 (4) |
C4—C3 | 1.378 (4) | C16—H16 | 0.9300 |
C4—C5 | 1.387 (3) | C10—C9 | 1.519 (4) |
C4—C7 | 1.487 (3) | C10—H10A | 0.9700 |
C13—C8 | 1.469 (3) | C10—H10B | 0.9700 |
C13—C12 | 1.518 (3) | C9—H9A | 0.9700 |
C20—C15 | 1.385 (4) | C9—H9B | 0.9700 |
C20—C19 | 1.389 (4) | C17—C18 | 1.355 (4) |
C20—H20 | 0.9300 | C17—H17 | 0.9300 |
C15—C16 | 1.375 (4) | C2—H2 | 0.9300 |
C15—C14 | 1.498 (3) | ||
C21—O3—H3A | 109 (3) | C13—C8—C9 | 120.1 (2) |
O3—C21—H21A | 109.5 | C6—C1—C2 | 123.1 (3) |
O3—C21—H21B | 109.5 | C6—C1—F1 | 119.0 (3) |
H21A—C21—H21B | 109.5 | C2—C1—F1 | 118.0 (3) |
O3—C21—H21C | 109.5 | C18—C19—C20 | 118.9 (3) |
H21A—C21—H21C | 109.5 | C18—C19—H19 | 120.6 |
H21B—C21—H21C | 109.5 | C20—C19—H19 | 120.6 |
C8—N2—N1 | 116.5 (2) | C1—C6—C5 | 118.4 (2) |
C13—N3—N4 | 120.80 (19) | C1—C6—H6 | 120.8 |
C14—N4—N3 | 118.0 (2) | C5—C6—H6 | 120.8 |
C14—N4—H4 | 126.3 (18) | C10—C11—C12 | 109.3 (2) |
N3—N4—H4 | 115.7 (18) | C10—C11—H11A | 109.8 |
C7—N1—N2 | 119.6 (2) | C12—C11—H11A | 109.8 |
C7—N1—H1 | 120 (2) | C10—C11—H11B | 109.8 |
N2—N1—H1 | 120 (2) | C12—C11—H11B | 109.8 |
C3—C4—C5 | 118.6 (2) | H11A—C11—H11B | 108.3 |
C3—C4—C7 | 122.5 (2) | C6—C5—C4 | 120.9 (3) |
C5—C4—C7 | 118.9 (2) | C6—C5—H5 | 119.6 |
N3—C13—C8 | 127.8 (2) | C4—C5—H5 | 119.6 |
N3—C13—C12 | 113.2 (2) | C15—C16—C17 | 121.4 (3) |
C8—C13—C12 | 119.1 (2) | C15—C16—H16 | 119.3 |
O1—C7—N1 | 122.3 (2) | C17—C16—H16 | 119.3 |
O1—C7—C4 | 122.5 (2) | C11—C10—C9 | 110.8 (2) |
N1—C7—C4 | 115.1 (2) | C11—C10—H10A | 109.5 |
C15—C20—C19 | 119.7 (2) | C9—C10—H10A | 109.5 |
C15—C20—H20 | 120.2 | C11—C10—H10B | 109.5 |
C19—C20—H20 | 120.2 | C9—C10—H10B | 109.5 |
C16—C15—C20 | 119.3 (2) | H10A—C10—H10B | 108.1 |
C16—C15—C14 | 117.0 (2) | C8—C9—C10 | 114.7 (2) |
C20—C15—C14 | 123.7 (2) | C8—C9—H9A | 108.6 |
O2—C14—N4 | 121.9 (2) | C10—C9—H9A | 108.6 |
O2—C14—C15 | 121.7 (2) | C8—C9—H9B | 108.6 |
N4—C14—C15 | 116.4 (2) | C10—C9—H9B | 108.6 |
C11—C12—C13 | 114.3 (2) | H9A—C9—H9B | 107.6 |
C11—C12—H12A | 108.7 | C18—C17—C16 | 117.7 (3) |
C13—C12—H12A | 108.7 | C18—C17—H17 | 121.2 |
C11—C12—H12B | 108.7 | C16—C17—H17 | 121.2 |
C13—C12—H12B | 108.7 | C17—C18—F2 | 118.8 (3) |
H12A—C12—H12B | 107.6 | C17—C18—C19 | 123.1 (2) |
C4—C3—C2 | 120.6 (2) | F2—C18—C19 | 118.0 (3) |
C4—C3—H3 | 119.7 | C1—C2—C3 | 118.4 (3) |
C2—C3—H3 | 119.7 | C1—C2—H2 | 120.8 |
N2—C8—C13 | 116.9 (2) | C3—C2—H2 | 120.8 |
N2—C8—C9 | 123.1 (2) | ||
C13—N3—N4—C14 | −177.1 (2) | C12—C13—C8—N2 | 174.3 (2) |
C8—N2—N1—C7 | −160.1 (2) | N3—C13—C8—C9 | 173.3 (2) |
N4—N3—C13—C8 | −1.2 (4) | C12—C13—C8—C9 | −6.0 (4) |
N4—N3—C13—C12 | 178.1 (2) | C15—C20—C19—C18 | 0.2 (4) |
N2—N1—C7—O1 | 8.5 (4) | C2—C1—C6—C5 | 0.4 (5) |
N2—N1—C7—C4 | −174.7 (2) | F1—C1—C6—C5 | 179.8 (3) |
C3—C4—C7—O1 | −145.9 (3) | C13—C12—C11—C10 | 50.5 (3) |
C5—C4—C7—O1 | 32.6 (4) | C1—C6—C5—C4 | 0.3 (4) |
C3—C4—C7—N1 | 37.3 (4) | C3—C4—C5—C6 | −0.9 (4) |
C5—C4—C7—N1 | −144.2 (3) | C7—C4—C5—C6 | −179.5 (3) |
C19—C20—C15—C16 | 0.1 (4) | C20—C15—C16—C17 | 0.0 (4) |
C19—C20—C15—C14 | −179.6 (3) | C14—C15—C16—C17 | 179.7 (3) |
N3—N4—C14—O2 | −1.7 (4) | C12—C11—C10—C9 | −65.6 (3) |
N3—N4—C14—C15 | 178.2 (2) | N2—C8—C9—C10 | 171.0 (3) |
C16—C15—C14—O2 | −5.9 (4) | C13—C8—C9—C10 | −8.8 (4) |
C20—C15—C14—O2 | 173.8 (3) | C11—C10—C9—C8 | 44.5 (3) |
C16—C15—C14—N4 | 174.2 (2) | C15—C16—C17—C18 | −0.3 (5) |
C20—C15—C14—N4 | −6.0 (4) | C16—C17—C18—F2 | −178.3 (3) |
N3—C13—C12—C11 | 165.4 (2) | C16—C17—C18—C19 | 0.6 (5) |
C8—C13—C12—C11 | −15.3 (4) | C20—C19—C18—C17 | −0.5 (5) |
C5—C4—C3—C2 | 0.8 (4) | C20—C19—C18—F2 | 178.4 (3) |
C7—C4—C3—C2 | 179.4 (3) | C6—C1—C2—C3 | −0.5 (5) |
N1—N2—C8—C13 | −175.0 (2) | F1—C1—C2—C3 | −179.9 (3) |
N1—N2—C8—C9 | 5.2 (4) | C4—C3—C2—C1 | −0.1 (4) |
N3—C13—C8—N2 | −6.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2 | 0.85 (3) | 1.93 (3) | 2.611 (3) | 137 (2) |
O3—H3A···N3 | 0.79 (4) | 2.11 (4) | 2.875 (3) | 161 (4) |
[ZnCl2(C20H18F2N4O2)] | F(000) = 1056 |
Mr = 520.65 | Dx = 1.587 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.7682 (5) Å | Cell parameters from 19667 reflections |
b = 17.3071 (7) Å | θ = 2.0–30.6° |
c = 13.3524 (7) Å | µ = 1.41 mm−1 |
β = 105.165 (4)° | T = 296 K |
V = 2178.74 (19) Å3 | Prism, yellow |
Z = 4 | 0.64 × 0.38 × 0.22 mm |
Stoe IPDS 2 diffractometer | 6409 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3712 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.078 |
Detector resolution: 6.67 pixels mm-1 | θmax = 30.2°, θmin = 2.0° |
rotation method scans | h = −13→13 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −24→23 |
Tmin = 0.510, Tmax = 0.767 | l = −18→18 |
21812 measured reflections |
Refinement on F2 | 48 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.077 | H-atom parameters constrained |
wR(F2) = 0.199 | w = 1/[σ2(Fo2) + (0.0859P)2 + 1.9025P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6409 reflections | Δρmax = 0.52 e Å−3 |
281 parameters | Δρmin = −0.47 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of LF, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite. Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997). |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.19181 (6) | 0.70598 (3) | 0.54901 (5) | 0.05246 (18) | |
Cl2 | 0.01999 (14) | 0.77893 (8) | 0.46033 (13) | 0.0703 (4) | |
Cl1 | 0.2705 (2) | 0.71079 (10) | 0.71779 (12) | 0.0819 (4) | |
O1 | 0.1684 (3) | 0.59503 (19) | 0.4980 (3) | 0.0571 (8) | |
F2 | 0.2590 (4) | 0.27168 (18) | 0.3162 (3) | 0.0835 (11) | |
N3 | 0.5860 (4) | 0.6720 (2) | 0.3910 (3) | 0.0492 (8) | |
N1 | 0.3594 (4) | 0.6238 (2) | 0.4391 (3) | 0.0483 (8) | |
H1 | 0.421951 | 0.610293 | 0.407526 | 0.058* | |
N4 | 0.6968 (4) | 0.6576 (2) | 0.3497 (3) | 0.0508 (9) | |
H4 | 0.758323 | 0.692937 | 0.348394 | 0.061* | |
N2 | 0.3557 (4) | 0.6969 (2) | 0.4781 (3) | 0.0473 (8) | |
F1 | 1.1319 (5) | 0.5202 (3) | 0.1138 (3) | 0.1075 (14) | |
O2 | 0.6224 (5) | 0.5357 (3) | 0.3142 (4) | 0.0893 (15) | |
C1 | 0.2586 (5) | 0.5739 (3) | 0.4532 (4) | 0.0483 (9) | |
C8 | 0.4467 (5) | 0.7493 (2) | 0.4697 (4) | 0.0466 (9) | |
C2 | 0.2610 (5) | 0.4946 (3) | 0.4151 (4) | 0.0479 (9) | |
C16 | 0.9308 (5) | 0.6247 (3) | 0.2591 (4) | 0.0529 (11) | |
H16 | 0.930078 | 0.672740 | 0.290291 | 0.064* | |
C15 | 0.8279 (5) | 0.5709 (3) | 0.2626 (3) | 0.0482 (10) | |
C14 | 0.7081 (5) | 0.5858 (3) | 0.3104 (4) | 0.0538 (11) | |
C3 | 0.3707 (5) | 0.4666 (3) | 0.3757 (4) | 0.0549 (11) | |
H3 | 0.444737 | 0.499317 | 0.371927 | 0.066* | |
C17 | 1.0353 (5) | 0.6076 (3) | 0.2094 (4) | 0.0620 (13) | |
H17 | 1.105896 | 0.643234 | 0.207633 | 0.074* | |
C13 | 0.5671 (5) | 0.7398 (3) | 0.4236 (4) | 0.0473 (9) | |
C4 | 0.3709 (6) | 0.3914 (3) | 0.3426 (4) | 0.0582 (12) | |
H4A | 0.444624 | 0.372141 | 0.317747 | 0.070* | |
C7 | 0.1485 (5) | 0.4456 (3) | 0.4166 (4) | 0.0591 (12) | |
H7 | 0.073834 | 0.463939 | 0.441126 | 0.071* | |
C18 | 1.0318 (6) | 0.5371 (4) | 0.1633 (5) | 0.0693 (15) | |
C5 | 0.2581 (6) | 0.3460 (3) | 0.3475 (4) | 0.0580 (12) | |
C20 | 0.8284 (6) | 0.5001 (3) | 0.2158 (5) | 0.0647 (13) | |
H20 | 0.758710 | 0.464022 | 0.218068 | 0.078* | |
C12 | 0.6609 (7) | 0.8080 (3) | 0.4220 (6) | 0.0733 (13) | |
H12A | 0.752590 | 0.797740 | 0.469714 | 0.088* | |
H12B | 0.675424 | 0.811855 | 0.353031 | 0.088* | |
C6 | 0.1464 (7) | 0.3714 (3) | 0.3828 (5) | 0.0679 (14) | |
H6 | 0.071023 | 0.338822 | 0.383577 | 0.082* | |
C19 | 0.9318 (7) | 0.4819 (4) | 0.1652 (5) | 0.0773 (17) | |
H19 | 0.933085 | 0.434035 | 0.133773 | 0.093* | |
C9 | 0.4196 (7) | 0.8266 (3) | 0.5119 (6) | 0.0737 (13) | |
H9A | 0.334071 | 0.847954 | 0.466134 | 0.088* | |
H9B | 0.400906 | 0.818418 | 0.578941 | 0.088* | |
C10 | 0.5312 (8) | 0.8836 (4) | 0.5243 (6) | 0.0833 (12) | |
H10A | 0.488976 | 0.934266 | 0.524712 | 0.100* | |
H10B | 0.596824 | 0.875944 | 0.591942 | 0.100* | |
C11 | 0.6105 (8) | 0.8841 (4) | 0.4491 (6) | 0.0845 (12) | |
H11A | 0.692419 | 0.917203 | 0.474247 | 0.101* | |
H11B | 0.552395 | 0.907309 | 0.386107 | 0.101* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0449 (3) | 0.0530 (3) | 0.0640 (3) | 0.0010 (2) | 0.0223 (2) | −0.0069 (3) |
Cl2 | 0.0520 (7) | 0.0632 (7) | 0.0941 (10) | 0.0091 (6) | 0.0165 (7) | −0.0010 (7) |
Cl1 | 0.0963 (11) | 0.0831 (10) | 0.0636 (8) | 0.0024 (9) | 0.0163 (8) | −0.0063 (7) |
O1 | 0.0519 (18) | 0.0521 (18) | 0.074 (2) | −0.0067 (15) | 0.0275 (17) | −0.0095 (16) |
F2 | 0.113 (3) | 0.0467 (15) | 0.103 (3) | −0.0188 (17) | 0.048 (2) | −0.0197 (16) |
N3 | 0.0446 (19) | 0.051 (2) | 0.056 (2) | 0.0066 (16) | 0.0215 (17) | −0.0021 (17) |
N1 | 0.0435 (18) | 0.0417 (18) | 0.063 (2) | 0.0012 (15) | 0.0187 (17) | −0.0063 (16) |
N4 | 0.052 (2) | 0.0467 (19) | 0.062 (2) | 0.0044 (16) | 0.0289 (19) | 0.0025 (17) |
N2 | 0.0429 (17) | 0.0418 (18) | 0.062 (2) | 0.0013 (14) | 0.0216 (16) | −0.0084 (16) |
F1 | 0.099 (3) | 0.135 (4) | 0.113 (3) | 0.027 (3) | 0.070 (3) | −0.011 (3) |
O2 | 0.078 (3) | 0.076 (3) | 0.136 (4) | −0.028 (2) | 0.067 (3) | −0.037 (3) |
C1 | 0.045 (2) | 0.046 (2) | 0.053 (2) | −0.0015 (18) | 0.012 (2) | −0.0036 (19) |
C8 | 0.044 (2) | 0.042 (2) | 0.055 (2) | 0.0002 (17) | 0.0153 (19) | −0.0070 (18) |
C2 | 0.049 (2) | 0.044 (2) | 0.052 (2) | 0.0013 (18) | 0.014 (2) | 0.0011 (18) |
C16 | 0.053 (2) | 0.051 (2) | 0.058 (3) | 0.009 (2) | 0.020 (2) | 0.004 (2) |
C15 | 0.048 (2) | 0.052 (2) | 0.047 (2) | 0.0099 (19) | 0.016 (2) | 0.0032 (19) |
C14 | 0.050 (2) | 0.058 (3) | 0.059 (3) | 0.005 (2) | 0.023 (2) | −0.002 (2) |
C3 | 0.055 (3) | 0.045 (2) | 0.069 (3) | −0.008 (2) | 0.024 (2) | −0.009 (2) |
C17 | 0.051 (3) | 0.074 (3) | 0.068 (3) | 0.004 (2) | 0.028 (2) | 0.010 (3) |
C13 | 0.044 (2) | 0.048 (2) | 0.052 (2) | 0.0010 (18) | 0.0169 (19) | −0.0048 (19) |
C4 | 0.065 (3) | 0.048 (2) | 0.065 (3) | −0.002 (2) | 0.023 (3) | −0.009 (2) |
C7 | 0.054 (3) | 0.056 (3) | 0.072 (3) | −0.007 (2) | 0.025 (2) | −0.003 (2) |
C18 | 0.071 (3) | 0.081 (4) | 0.067 (3) | 0.020 (3) | 0.037 (3) | 0.003 (3) |
C5 | 0.079 (3) | 0.041 (2) | 0.056 (3) | −0.007 (2) | 0.022 (3) | −0.0051 (19) |
C20 | 0.060 (3) | 0.061 (3) | 0.076 (4) | 0.002 (2) | 0.023 (3) | −0.012 (3) |
C12 | 0.073 (3) | 0.060 (2) | 0.101 (3) | −0.009 (2) | 0.047 (3) | −0.003 (2) |
C6 | 0.073 (3) | 0.059 (3) | 0.079 (4) | −0.023 (3) | 0.031 (3) | −0.006 (3) |
C19 | 0.090 (4) | 0.070 (4) | 0.077 (4) | 0.021 (3) | 0.030 (3) | −0.020 (3) |
C9 | 0.078 (3) | 0.053 (2) | 0.107 (3) | −0.0073 (19) | 0.053 (3) | −0.019 (2) |
C10 | 0.087 (3) | 0.059 (2) | 0.117 (3) | −0.0146 (19) | 0.049 (2) | −0.018 (2) |
C11 | 0.088 (3) | 0.061 (2) | 0.117 (3) | −0.014 (2) | 0.049 (2) | −0.014 (2) |
Zn1—O1 | 2.030 (3) | C3—C4 | 1.375 (7) |
Zn1—N2 | 2.068 (3) | C3—H3 | 0.9300 |
Zn1—Cl1 | 2.1842 (17) | C17—C18 | 1.363 (8) |
Zn1—Cl2 | 2.1848 (15) | C17—H17 | 0.9300 |
O1—C1 | 1.243 (5) | C13—C12 | 1.497 (7) |
F2—C5 | 1.353 (6) | C4—C5 | 1.368 (7) |
N3—C13 | 1.281 (6) | C4—H4A | 0.9300 |
N3—N4 | 1.360 (5) | C7—C6 | 1.360 (8) |
N1—C1 | 1.360 (6) | C7—H7 | 0.9300 |
N1—N2 | 1.372 (5) | C18—C19 | 1.372 (9) |
N1—H1 | 0.8600 | C5—C6 | 1.370 (8) |
N4—C14 | 1.366 (6) | C20—C19 | 1.391 (8) |
N4—H4 | 0.8600 | C20—H20 | 0.9300 |
N2—C8 | 1.296 (5) | C12—C11 | 1.484 (8) |
F1—C18 | 1.347 (6) | C12—H12A | 0.9700 |
O2—C14 | 1.215 (6) | C12—H12B | 0.9700 |
C1—C2 | 1.466 (6) | C6—H6 | 0.9300 |
C8—C13 | 1.472 (6) | C19—H19 | 0.9300 |
C8—C9 | 1.502 (6) | C9—C10 | 1.447 (8) |
C2—C7 | 1.392 (6) | C9—H9A | 0.9700 |
C2—C3 | 1.398 (6) | C9—H9B | 0.9700 |
C16—C15 | 1.380 (7) | C10—C11 | 1.420 (9) |
C16—C17 | 1.388 (7) | C10—H10A | 0.9700 |
C16—H16 | 0.9300 | C10—H10B | 0.9700 |
C15—C20 | 1.377 (7) | C11—H11A | 0.9700 |
C15—C14 | 1.494 (6) | C11—H11B | 0.9700 |
O1—Zn1—N2 | 78.88 (13) | C5—C4—H4A | 121.3 |
O1—Zn1—Cl1 | 111.12 (12) | C3—C4—H4A | 121.3 |
N2—Zn1—Cl1 | 111.68 (13) | C6—C7—C2 | 120.9 (5) |
O1—Zn1—Cl2 | 111.20 (12) | C6—C7—H7 | 119.5 |
N2—Zn1—Cl2 | 111.90 (12) | C2—C7—H7 | 119.5 |
Cl1—Zn1—Cl2 | 123.39 (7) | F1—C18—C17 | 118.7 (6) |
C1—O1—Zn1 | 114.1 (3) | F1—C18—C19 | 118.0 (5) |
C13—N3—N4 | 120.4 (4) | C17—C18—C19 | 123.3 (5) |
C1—N1—N2 | 116.1 (3) | F2—C5—C4 | 117.4 (5) |
C1—N1—H1 | 121.9 | F2—C5—C6 | 118.8 (5) |
N2—N1—H1 | 121.9 | C4—C5—C6 | 123.8 (5) |
N3—N4—C14 | 118.4 (4) | C15—C20—C19 | 120.8 (5) |
N3—N4—H4 | 120.8 | C15—C20—H20 | 119.6 |
C14—N4—H4 | 120.8 | C19—C20—H20 | 119.6 |
C8—N2—N1 | 121.7 (3) | C11—C12—C13 | 116.9 (5) |
C8—N2—Zn1 | 128.1 (3) | C11—C12—H12A | 108.1 |
N1—N2—Zn1 | 110.2 (3) | C13—C12—H12A | 108.1 |
O1—C1—N1 | 120.7 (4) | C11—C12—H12B | 108.1 |
O1—C1—C2 | 121.4 (4) | C13—C12—H12B | 108.1 |
N1—C1—C2 | 117.9 (4) | H12A—C12—H12B | 107.3 |
N2—C8—C13 | 126.9 (4) | C7—C6—C5 | 118.2 (5) |
N2—C8—C9 | 113.5 (4) | C7—C6—H6 | 120.9 |
C13—C8—C9 | 119.7 (4) | C5—C6—H6 | 120.9 |
C7—C2—C3 | 118.7 (4) | C18—C19—C20 | 117.6 (5) |
C7—C2—C1 | 118.7 (4) | C18—C19—H19 | 121.2 |
C3—C2—C1 | 122.6 (4) | C20—C19—H19 | 121.2 |
C15—C16—C17 | 120.4 (5) | C10—C9—C8 | 116.7 (5) |
C15—C16—H16 | 119.8 | C10—C9—H9A | 108.1 |
C17—C16—H16 | 119.8 | C8—C9—H9A | 108.1 |
C20—C15—C16 | 119.8 (4) | C10—C9—H9B | 108.1 |
C20—C15—C14 | 116.3 (4) | C8—C9—H9B | 108.1 |
C16—C15—C14 | 123.9 (4) | H9A—C9—H9B | 107.3 |
O2—C14—N4 | 120.5 (4) | C11—C10—C9 | 117.2 (6) |
O2—C14—C15 | 121.4 (4) | C11—C10—H10A | 108.0 |
N4—C14—C15 | 118.1 (4) | C9—C10—H10A | 108.0 |
C4—C3—C2 | 121.0 (4) | C11—C10—H10B | 108.0 |
C4—C3—H3 | 119.5 | C9—C10—H10B | 108.0 |
C2—C3—H3 | 119.5 | H10A—C10—H10B | 107.2 |
C18—C17—C16 | 118.2 (5) | C10—C11—C12 | 116.4 (6) |
C18—C17—H17 | 120.9 | C10—C11—H11A | 108.2 |
C16—C17—H17 | 120.9 | C12—C11—H11A | 108.2 |
N3—C13—C8 | 116.5 (4) | C10—C11—H11B | 108.2 |
N3—C13—C12 | 125.0 (4) | C12—C11—H11B | 108.2 |
C8—C13—C12 | 118.5 (4) | H11A—C11—H11B | 107.4 |
C5—C4—C3 | 117.3 (5) | ||
C13—N3—N4—C14 | −176.2 (5) | N4—N3—C13—C12 | −0.9 (8) |
C1—N1—N2—C8 | 179.7 (4) | N2—C8—C13—N3 | −2.0 (8) |
C1—N1—N2—Zn1 | 0.5 (5) | C9—C8—C13—N3 | 178.6 (5) |
Zn1—O1—C1—N1 | −1.7 (6) | N2—C8—C13—C12 | −179.6 (5) |
Zn1—O1—C1—C2 | 177.6 (3) | C9—C8—C13—C12 | 1.0 (8) |
N2—N1—C1—O1 | 0.8 (7) | C2—C3—C4—C5 | 1.4 (8) |
N2—N1—C1—C2 | −178.5 (4) | C3—C2—C7—C6 | 1.5 (8) |
N1—N2—C8—C13 | −2.7 (7) | C1—C2—C7—C6 | −179.5 (5) |
Zn1—N2—C8—C13 | 176.5 (4) | C16—C17—C18—F1 | 179.3 (5) |
N1—N2—C8—C9 | 176.7 (5) | C16—C17—C18—C19 | −1.2 (9) |
Zn1—N2—C8—C9 | −4.2 (7) | C3—C4—C5—F2 | −179.1 (5) |
O1—C1—C2—C7 | 8.9 (7) | C3—C4—C5—C6 | 0.4 (9) |
N1—C1—C2—C7 | −171.8 (5) | C16—C15—C20—C19 | 0.2 (8) |
O1—C1—C2—C3 | −172.1 (5) | C14—C15—C20—C19 | 177.2 (5) |
N1—C1—C2—C3 | 7.2 (7) | N3—C13—C12—C11 | 171.5 (6) |
C17—C16—C15—C20 | −0.5 (8) | C8—C13—C12—C11 | −11.1 (9) |
C17—C16—C15—C14 | −177.3 (5) | C2—C7—C6—C5 | 0.3 (9) |
N3—N4—C14—O2 | −1.4 (8) | F2—C5—C6—C7 | 178.3 (5) |
N3—N4—C14—C15 | 178.4 (4) | C4—C5—C6—C7 | −1.2 (9) |
C20—C15—C14—O2 | 5.3 (8) | F1—C18—C19—C20 | −179.6 (6) |
C16—C15—C14—O2 | −177.8 (5) | C17—C18—C19—C20 | 1.0 (10) |
C20—C15—C14—N4 | −174.4 (5) | C15—C20—C19—C18 | −0.4 (9) |
C16—C15—C14—N4 | 2.4 (7) | N2—C8—C9—C10 | 168.1 (6) |
C7—C2—C3—C4 | −2.3 (8) | C13—C8—C9—C10 | −12.5 (9) |
C1—C2—C3—C4 | 178.7 (5) | C8—C9—C10—C11 | 35.5 (10) |
C15—C16—C17—C18 | 1.0 (8) | C9—C10—C11—C12 | −46.5 (11) |
N4—N3—C13—C8 | −178.3 (4) | C13—C12—C11—C10 | 33.6 (10) |
[HgCl2(C20H18F2N4O2)] | F(000) = 1256 |
Mr = 655.87 | Dx = 2.008 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.4902 (4) Å | Cell parameters from 14848 reflections |
b = 16.7227 (8) Å | θ = 2.3–31.5° |
c = 12.6827 (5) Å | µ = 7.38 mm−1 |
β = 102.769 (3)° | T = 296 K |
V = 2169.83 (16) Å3 | Prism, yellow |
Z = 4 | 0.47 × 0.27 × 0.12 mm |
Stoe IPDS 2 diffractometer | 1875 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 1756 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.047 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.1°, θmin = 2.3° |
rotation method scans | h = −12→12 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −19→19 |
Tmin = 0.207, Tmax = 0.498 | l = −13→14 |
7006 measured reflections |
Refinement on F2 | 71 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.062 | w = 1/[σ2(Fo2) + (0.0337P)2 + 2.9357P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.002 |
1875 reflections | Δρmax = 0.94 e Å−3 |
141 parameters | Δρmin = −0.72 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. STOE diffractometer equipped with an IPDS II image plate detector was used to collect the crystal data of LF, 1 and 2. The collection was carried out at room temperature (296K) using graphite monochromated Mo Kα radiation (λ=0.71073Å) inω-scanning mode. SHELXS-97(Sheldrick, 1997)was used to solve (direct methods) and refine (full-matrix least-squares method) the structures, implemented in the WinGX (Farrugia, 1999)program suite. Data collection: X-AREA and data reduction: X-RED32 (Cie, 2002). All non-hydrogen atoms were assigned anisotropic thermal parameters. Experimental details of the crystal data, data collection and refinement are illustrated inTable 1. The structure analysis and presentation of the results were done by the general-purpose crystallographic tool PLATON(Spek, 2009), while themolecular graphics were made by ORTEP-3 for Windows(Farrugia, 1997). |
x | y | z | Uiso*/Ueq | ||
Hg1 | 0.500000 | 0.65290 (2) | 0.750000 | 0.04720 (11) | |
F1 | 1.0855 (3) | 0.5866 (2) | 0.3494 (3) | 0.0696 (8) | |
N2 | 0.6516 (3) | 0.51689 (19) | 0.6058 (3) | 0.0424 (7) | |
H2 | 0.690358 | 0.474158 | 0.591702 | 0.051* | |
C3 | 0.8594 (5) | 0.6532 (2) | 0.5040 (4) | 0.0511 (11) | |
H3 | 0.843729 | 0.697804 | 0.542989 | 0.061* | |
C8 | 0.5457 (4) | 0.4456 (2) | 0.7125 (3) | 0.0382 (7) | |
C4 | 0.9615 (5) | 0.6542 (3) | 0.4522 (5) | 0.0547 (11) | |
H4 | 1.015527 | 0.698667 | 0.455775 | 0.066* | |
C2 | 0.7790 (4) | 0.5863 (2) | 0.4991 (4) | 0.0402 (9) | |
C9 | 0.6077 (5) | 0.3686 (2) | 0.6904 (4) | 0.0513 (9) | |
H9A | 0.585428 | 0.358532 | 0.613139 | 0.062* | |
H9B | 0.701942 | 0.374285 | 0.711759 | 0.062* | |
C5 | 0.9806 (4) | 0.5882 (3) | 0.3957 (4) | 0.0489 (10) | |
C1 | 0.6763 (4) | 0.5882 (2) | 0.5626 (4) | 0.0459 (10) | |
C7 | 0.7989 (4) | 0.5215 (2) | 0.4369 (4) | 0.0422 (9) | |
H7 | 0.743705 | 0.477409 | 0.430856 | 0.051* | |
C10 | 0.5677 (6) | 0.2982 (3) | 0.7473 (6) | 0.0685 (12) | |
H10A | 0.585476 | 0.249945 | 0.710576 | 0.082* | |
H10B | 0.620898 | 0.296542 | 0.820238 | 0.082* | |
C6 | 0.9004 (5) | 0.5220 (3) | 0.3838 (4) | 0.0488 (10) | |
H6 | 0.914304 | 0.478947 | 0.341211 | 0.059* | |
N1 | 0.5645 (3) | 0.5138 (2) | 0.6718 (3) | 0.0405 (6) | |
O2 | 0.6206 (5) | 0.64934 (19) | 0.5777 (4) | 0.0746 (13) | |
Cl1 | 0.69446 (14) | 0.68047 (9) | 0.87181 (15) | 0.0789 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.04234 (14) | 0.04600 (15) | 0.05688 (18) | 0.000 | 0.01874 (10) | 0.000 |
F1 | 0.0507 (15) | 0.106 (2) | 0.062 (2) | 0.0051 (15) | 0.0333 (14) | 0.0133 (16) |
N2 | 0.0440 (16) | 0.0395 (15) | 0.052 (2) | 0.0048 (13) | 0.0288 (13) | 0.0030 (13) |
C3 | 0.059 (3) | 0.042 (2) | 0.059 (3) | −0.0009 (19) | 0.027 (2) | −0.0013 (19) |
C8 | 0.0359 (15) | 0.0380 (13) | 0.0455 (19) | −0.0002 (13) | 0.0194 (15) | −0.0001 (12) |
C4 | 0.051 (3) | 0.054 (2) | 0.064 (3) | −0.013 (2) | 0.021 (2) | 0.006 (2) |
C2 | 0.044 (2) | 0.0378 (19) | 0.043 (2) | 0.0029 (16) | 0.0184 (18) | 0.0071 (16) |
C9 | 0.0517 (19) | 0.0437 (16) | 0.066 (2) | 0.0059 (15) | 0.0296 (17) | −0.0036 (16) |
C5 | 0.036 (2) | 0.072 (3) | 0.042 (3) | 0.0020 (19) | 0.0165 (18) | 0.012 (2) |
C1 | 0.050 (2) | 0.041 (2) | 0.053 (3) | 0.0035 (18) | 0.026 (2) | 0.0062 (18) |
C7 | 0.046 (2) | 0.041 (2) | 0.041 (2) | −0.0002 (17) | 0.0138 (18) | 0.0022 (16) |
C10 | 0.075 (3) | 0.049 (2) | 0.092 (3) | 0.004 (2) | 0.043 (2) | 0.005 (2) |
C6 | 0.054 (2) | 0.058 (3) | 0.037 (3) | 0.010 (2) | 0.0181 (19) | 0.0000 (18) |
N1 | 0.0379 (14) | 0.0427 (10) | 0.0470 (18) | 0.0012 (12) | 0.0228 (12) | 0.0050 (10) |
O2 | 0.097 (3) | 0.0472 (18) | 0.103 (3) | 0.0241 (18) | 0.073 (3) | 0.0219 (17) |
Cl1 | 0.0568 (7) | 0.0628 (7) | 0.1067 (12) | −0.0105 (6) | −0.0044 (7) | 0.0040 (7) |
Hg1—Cl1 | 2.3167 (14) | C4—C5 | 1.354 (7) |
Hg1—Cl1i | 2.3168 (14) | C4—H4 | 0.9300 |
Hg1—N1 | 2.674 (3) | C2—C7 | 1.383 (6) |
Hg1—N1i | 2.674 (3) | C2—C1 | 1.481 (6) |
Hg1—O1 | 2.757 | C9—C10 | 1.489 (6) |
Hg1—O2 | 2.757 | C9—H9A | 0.9700 |
F1—C5 | 1.358 (5) | C9—H9B | 0.9700 |
N2—C1 | 1.361 (5) | C5—C6 | 1.379 (7) |
N2—N1 | 1.371 (4) | C1—O2 | 1.213 (5) |
N2—H2 | 0.8600 | C7—C6 | 1.380 (6) |
C3—C4 | 1.375 (7) | C7—H7 | 0.9300 |
C3—C2 | 1.394 (6) | C10—C10i | 1.437 (11) |
C3—H3 | 0.9300 | C10—H10A | 0.9700 |
C8—N1 | 1.284 (5) | C10—H10B | 0.9700 |
C8—C8i | 1.493 (7) | C6—H6 | 0.9300 |
C8—C9 | 1.497 (6) | ||
Cl1—Hg1—Cl1i | 157.05 (8) | C8—C9—H9A | 108.7 |
Cl1—Hg1—N1 | 99.37 (9) | C10—C9—H9B | 108.7 |
Cl1i—Hg1—N1 | 100.57 (9) | C8—C9—H9B | 108.7 |
Cl1—Hg1—N1i | 100.57 (9) | H9A—C9—H9B | 107.6 |
Cl1i—Hg1—N1i | 99.37 (9) | C4—C5—F1 | 118.3 (4) |
Cl1—Hg1—O2 | 92.42 (9) | C4—C5—C6 | 123.7 (4) |
Cl1—Hg1—O2i | 88.08 (9) | F1—C5—C6 | 118.0 (4) |
N1—Hg1—N1i | 59.05 (14) | O2—C1—N2 | 122.3 (4) |
C1—N2—N1 | 119.4 (3) | O2—C1—C2 | 122.5 (4) |
C1—N2—H2 | 120.3 | N2—C1—C2 | 115.2 (3) |
N1—N2—H2 | 120.3 | C6—C7—C2 | 120.3 (4) |
C4—C3—C2 | 121.1 (4) | C6—C7—H7 | 119.9 |
C4—C3—H3 | 119.4 | C2—C7—H7 | 119.9 |
C2—C3—H3 | 119.4 | C10i—C10—C9 | 114.3 (5) |
N1—C8—C8i | 115.7 (2) | C10i—C10—H10A | 108.7 |
N1—C8—C9 | 125.2 (3) | C9—C10—H10A | 108.7 |
C8i—C8—C9 | 119.1 (2) | C10i—C10—H10B | 108.7 |
C5—C4—C3 | 117.7 (4) | C9—C10—H10B | 108.7 |
C5—C4—H4 | 121.2 | H10A—C10—H10B | 107.6 |
C3—C4—H4 | 121.2 | C5—C6—C7 | 118.0 (4) |
C7—C2—C3 | 119.2 (4) | C5—C6—H6 | 121.0 |
C7—C2—C1 | 123.2 (4) | C7—C6—H6 | 121.0 |
C3—C2—C1 | 117.6 (4) | C8—N1—N2 | 117.5 (3) |
C10—C9—C8 | 114.1 (4) | C8—N1—Hg1 | 123.3 (3) |
C10—C9—H9A | 108.7 | N2—N1—Hg1 | 116.8 (2) |
C2—C3—C4—C5 | 0.4 (8) | C3—C2—C7—C6 | 2.5 (7) |
C4—C3—C2—C7 | −3.0 (7) | C1—C2—C7—C6 | −176.9 (4) |
C4—C3—C2—C1 | 176.4 (5) | C8—C9—C10—C10i | 38.4 (9) |
N1—C8—C9—C10 | −179.3 (5) | C4—C5—C6—C7 | −3.3 (7) |
C8i—C8—C9—C10 | 0.7 (8) | F1—C5—C6—C7 | 175.7 (4) |
C3—C4—C5—F1 | −176.2 (4) | C2—C7—C6—C5 | 0.6 (7) |
C3—C4—C5—C6 | 2.8 (8) | C8i—C8—N1—N2 | 177.6 (4) |
N1—N2—C1—O2 | −2.4 (7) | C9—C8—N1—N2 | −2.4 (7) |
N1—N2—C1—C2 | 175.7 (4) | C8i—C8—N1—Hg1 | 15.7 (6) |
C7—C2—C1—O2 | −147.4 (5) | C9—C8—N1—Hg1 | −164.3 (4) |
C3—C2—C1—O2 | 33.3 (7) | C1—N2—N1—C8 | −178.7 (4) |
C7—C2—C1—N2 | 34.6 (6) | C1—N2—N1—Hg1 | −15.6 (5) |
C3—C2—C1—N2 | −144.8 (4) |
Symmetry code: (i) −x+1, y, −z+3/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···F1ii | 0.86 | 2.52 | 3.198 (4) | 137 |
C9—H9B···F1ii | 0.97 | 2.60 | 3.447 (5) | 146 |
Symmetry code: (ii) −x+2, −y+1, −z+1. |
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