The heteroscorpionate ligand 2,2-bis(3,5-dimethylpyrazol-1-yl)-1,1-diphenylethanol, C
24H
26N
4O, features in the solid state an intramolecular O—H
N hydrogen bond. A heteroscorpionate tungsten complex,
cis-[2,2-bis(3,5-dimethylpyrazolyl)-1,1-diphenylethanolato]chloridodioxidotungsten(VI) tetrahydrofuran monosolvate, [W(C
24H
25N
4O)ClO
2]·C
4H
8O, was prepared by the simple mixing of solutions of the ligand and WOCl
4 in tetrahydrofuran. The tungsten complex was isolated after standing for several weeks. The complex exhibits a κ
3N,
N′,
O-coordination of the ligand. This simple synthetic procedure allows access to the
cis isomer in high yield without additional purification steps. The Hirshfeld surface analysis shows a change of the intermolecular contacts due to the coordination of the WO
2Cl unit with the ligand molecule.
Supporting information
CCDC references: 1922641; 1922640
For both structures, data collection: X-AREA (Stoe & Cie, 2009); cell refinement: X-AREA (Stoe & Cie, 2009); data reduction: X-RED (Stoe & Cie, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2017 (Sheldrick 2015) for (1); SHELXL2014 (Sheldrick 2015) for (2). For both structures, molecular graphics: ORTEP-3 (Farrugia, 2012). Software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015) for (1); SHELXL2014 (Sheldrick, 2015) for (2).
2,2-Bis(3,5-dimethylpyrazol-1-yl)-1,1-diphenylethanol (1)
top
Crystal data top
C24H26N4O | Dx = 1.220 Mg m−3 |
Mr = 386.49 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 25184 reflections |
a = 19.0555 (6) Å | θ = 2.5–28.3° |
b = 12.3840 (5) Å | µ = 0.08 mm−1 |
c = 17.8388 (7) Å | T = 193 K |
V = 4209.7 (3) Å3 | Prism, colourless |
Z = 8 | 0.45 × 0.25 × 0.10 mm |
F(000) = 1648 | |
Data collection top
Stoe IPDS 2T diffractometer | 4826 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3611 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.038 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
rotation method scans | h = −24→24 |
Absorption correction: integration (X-RED; Stoe & Cie, 2009) | k = −16→14 |
Tmin = 0.789, Tmax = 0.958 | l = −23→21 |
35928 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0332P)2 + 1.8904P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
4826 reflections | Δρmax = 0.17 e Å−3 |
281 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | |
Special details top
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. The
structures were solved by direct methods with SHELXS-97 and refined by
full-matrix least-squares methods on F2 for all unique reflections
with SHELXL-2014 (Sheldrick, 2008). Crystal data, data collection and
structure refinement details are summarized in Table 1. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.71727 (6) | 0.50955 (11) | 0.88355 (7) | 0.0350 (3) | |
N2 | 0.67600 (7) | 0.41980 (12) | 0.87326 (8) | 0.0422 (3) | |
C1 | 0.75933 (13) | 0.67620 (18) | 0.81894 (12) | 0.0570 (5) | |
H1A | 0.7414 (14) | 0.732 (2) | 0.8544 (14) | 0.088 (8)* | |
H1B | 0.7562 (13) | 0.704 (2) | 0.7666 (14) | 0.086 (8)* | |
H1C | 0.8100 (13) | 0.6619 (19) | 0.8291 (13) | 0.076 (7)* | |
C2 | 0.71683 (9) | 0.57615 (15) | 0.82281 (9) | 0.0435 (4) | |
C3 | 0.67211 (11) | 0.52885 (18) | 0.77236 (10) | 0.0540 (5) | |
H3 | 0.659603 | 0.555883 | 0.724349 | 0.065* | |
C4 | 0.64862 (9) | 0.43359 (17) | 0.80515 (10) | 0.0486 (5) | |
C5 | 0.60017 (11) | 0.3506 (2) | 0.77200 (12) | 0.0691 (7) | |
H5A | 0.593914 | 0.291176 | 0.807622 | 0.104* | |
H5B | 0.620409 | 0.322745 | 0.725362 | 0.104* | |
H5C | 0.554574 | 0.383922 | 0.761400 | 0.104* | |
N3 | 0.83274 (6) | 0.48078 (10) | 0.93218 (7) | 0.0327 (3) | |
N4 | 0.84198 (7) | 0.38179 (11) | 0.89939 (7) | 0.0367 (3) | |
C6 | 0.90057 (9) | 0.64422 (15) | 0.97612 (12) | 0.0501 (4) | |
H6A | 0.874254 | 0.696254 | 0.945738 | 0.075* | |
H6B | 0.950034 | 0.665703 | 0.978072 | 0.075* | |
H6C | 0.881268 | 0.642656 | 1.027024 | 0.075* | |
C7 | 0.89471 (8) | 0.53454 (13) | 0.94184 (9) | 0.0371 (3) | |
C8 | 0.94578 (9) | 0.46741 (15) | 0.91445 (9) | 0.0425 (4) | |
H8 | 0.994835 | 0.480981 | 0.913181 | 0.051* | |
C9 | 0.91115 (9) | 0.37467 (14) | 0.88865 (9) | 0.0390 (4) | |
C10 | 0.94185 (11) | 0.27706 (17) | 0.85142 (11) | 0.0551 (5) | |
H10A | 0.909468 | 0.216062 | 0.856714 | 0.083* | |
H10B | 0.986767 | 0.259088 | 0.875095 | 0.083* | |
H10C | 0.949407 | 0.292187 | 0.798106 | 0.083* | |
C11 | 0.76206 (7) | 0.51941 (13) | 0.94908 (8) | 0.0314 (3) | |
H11 | 0.766210 | 0.598305 | 0.960180 | 0.038* | |
C12 | 0.72902 (8) | 0.46565 (12) | 1.02000 (8) | 0.0316 (3) | |
O1 | 0.72289 (6) | 0.35238 (9) | 1.00893 (7) | 0.0385 (3) | |
H1D | 0.7002 (12) | 0.3486 (18) | 0.9631 (13) | 0.072 (7)* | |
C13 | 0.65677 (8) | 0.51540 (13) | 1.03702 (8) | 0.0328 (3) | |
C14 | 0.63903 (8) | 0.62154 (14) | 1.01928 (9) | 0.0402 (4) | |
H14 | 0.672179 | 0.666295 | 0.994452 | 0.048* | |
C15 | 0.57305 (9) | 0.66278 (16) | 1.03762 (10) | 0.0460 (4) | |
H15 | 0.561649 | 0.735230 | 1.025059 | 0.055* | |
C16 | 0.52431 (9) | 0.59915 (17) | 1.07384 (10) | 0.0484 (4) | |
H16 | 0.479290 | 0.627186 | 1.085857 | 0.058* | |
C17 | 0.54161 (9) | 0.49421 (16) | 1.09246 (10) | 0.0483 (4) | |
H17 | 0.508513 | 0.450207 | 1.118006 | 0.058* | |
C18 | 0.60715 (9) | 0.45252 (14) | 1.07406 (9) | 0.0410 (4) | |
H18 | 0.618217 | 0.380070 | 1.086975 | 0.049* | |
C19 | 0.77987 (8) | 0.48281 (13) | 1.08573 (8) | 0.0334 (3) | |
C20 | 0.82916 (9) | 0.40392 (14) | 1.10228 (10) | 0.0435 (4) | |
H20 | 0.829948 | 0.338932 | 1.074007 | 0.052* | |
C21 | 0.87740 (11) | 0.41891 (17) | 1.15980 (11) | 0.0537 (5) | |
H21 | 0.911179 | 0.364485 | 1.170137 | 0.064* | |
C22 | 0.87658 (10) | 0.5119 (2) | 1.20180 (10) | 0.0575 (5) | |
H22 | 0.909183 | 0.521588 | 1.241516 | 0.069* | |
C23 | 0.82806 (11) | 0.5907 (2) | 1.18574 (12) | 0.0659 (6) | |
H23 | 0.827410 | 0.655303 | 1.214450 | 0.079* | |
C24 | 0.77993 (10) | 0.57693 (17) | 1.12796 (11) | 0.0519 (5) | |
H24 | 0.746886 | 0.632287 | 1.117310 | 0.062* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0319 (6) | 0.0431 (7) | 0.0300 (6) | 0.0036 (6) | −0.0037 (5) | −0.0028 (5) |
N2 | 0.0341 (7) | 0.0538 (9) | 0.0386 (7) | −0.0011 (6) | −0.0075 (6) | −0.0103 (6) |
C1 | 0.0682 (14) | 0.0561 (12) | 0.0467 (11) | 0.0052 (11) | 0.0001 (10) | 0.0144 (9) |
C2 | 0.0451 (9) | 0.0534 (10) | 0.0320 (8) | 0.0140 (8) | 0.0000 (7) | 0.0006 (7) |
C3 | 0.0588 (11) | 0.0700 (13) | 0.0331 (8) | 0.0190 (10) | −0.0106 (8) | −0.0044 (8) |
C4 | 0.0382 (9) | 0.0681 (13) | 0.0393 (9) | 0.0118 (9) | −0.0098 (7) | −0.0164 (8) |
C5 | 0.0524 (12) | 0.0936 (17) | 0.0613 (13) | 0.0044 (12) | −0.0246 (10) | −0.0285 (12) |
N3 | 0.0294 (6) | 0.0350 (7) | 0.0337 (6) | 0.0016 (5) | −0.0005 (5) | −0.0016 (5) |
N4 | 0.0375 (7) | 0.0391 (7) | 0.0337 (6) | 0.0052 (6) | 0.0001 (5) | −0.0032 (5) |
C6 | 0.0369 (9) | 0.0447 (10) | 0.0687 (12) | −0.0065 (8) | −0.0035 (8) | −0.0032 (9) |
C7 | 0.0318 (8) | 0.0391 (8) | 0.0405 (8) | −0.0012 (7) | −0.0027 (6) | 0.0050 (7) |
C8 | 0.0301 (8) | 0.0517 (10) | 0.0458 (9) | 0.0036 (7) | 0.0013 (7) | 0.0084 (8) |
C9 | 0.0389 (8) | 0.0447 (9) | 0.0333 (8) | 0.0099 (7) | 0.0020 (6) | 0.0046 (7) |
C10 | 0.0558 (11) | 0.0577 (12) | 0.0518 (10) | 0.0186 (10) | 0.0083 (9) | −0.0031 (9) |
C11 | 0.0289 (7) | 0.0336 (8) | 0.0316 (7) | 0.0016 (6) | −0.0027 (6) | −0.0024 (6) |
C12 | 0.0341 (7) | 0.0288 (7) | 0.0320 (7) | −0.0032 (6) | −0.0026 (6) | −0.0021 (6) |
O1 | 0.0437 (6) | 0.0311 (6) | 0.0409 (6) | −0.0054 (5) | −0.0042 (5) | −0.0044 (5) |
C13 | 0.0319 (7) | 0.0370 (8) | 0.0295 (7) | −0.0052 (6) | −0.0021 (6) | −0.0037 (6) |
C14 | 0.0348 (8) | 0.0425 (9) | 0.0432 (9) | 0.0013 (7) | 0.0042 (7) | 0.0005 (7) |
C15 | 0.0388 (9) | 0.0515 (10) | 0.0478 (9) | 0.0074 (8) | 0.0009 (7) | −0.0038 (8) |
C16 | 0.0314 (8) | 0.0664 (12) | 0.0473 (10) | 0.0007 (8) | 0.0023 (7) | −0.0112 (9) |
C17 | 0.0375 (9) | 0.0615 (12) | 0.0458 (9) | −0.0149 (9) | 0.0065 (7) | −0.0061 (8) |
C18 | 0.0412 (9) | 0.0446 (9) | 0.0374 (8) | −0.0098 (7) | 0.0012 (7) | −0.0031 (7) |
C19 | 0.0335 (7) | 0.0379 (8) | 0.0286 (7) | −0.0036 (6) | −0.0002 (6) | −0.0004 (6) |
C20 | 0.0484 (10) | 0.0386 (9) | 0.0434 (9) | −0.0008 (8) | −0.0099 (7) | 0.0037 (7) |
C21 | 0.0521 (11) | 0.0587 (12) | 0.0504 (10) | −0.0012 (9) | −0.0165 (8) | 0.0118 (9) |
C22 | 0.0499 (10) | 0.0865 (15) | 0.0360 (9) | −0.0067 (11) | −0.0114 (8) | −0.0065 (9) |
C23 | 0.0517 (11) | 0.0870 (16) | 0.0589 (12) | 0.0048 (11) | −0.0140 (10) | −0.0381 (12) |
C24 | 0.0425 (9) | 0.0586 (12) | 0.0546 (10) | 0.0062 (9) | −0.0113 (8) | −0.0233 (9) |
Geometric parameters (Å, º) top
N1—C2 | 1.362 (2) | C10—H10C | 0.9800 |
N1—N2 | 1.3739 (19) | C11—C12 | 1.562 (2) |
N1—C11 | 1.4526 (18) | C11—H11 | 1.0000 |
N2—C4 | 1.333 (2) | C12—O1 | 1.4214 (18) |
C1—C2 | 1.482 (3) | C12—C19 | 1.5359 (19) |
C1—H1A | 1.00 (3) | C12—C13 | 1.539 (2) |
C1—H1B | 1.00 (3) | O1—H1D | 0.93 (2) |
C1—H1C | 1.00 (3) | C13—C18 | 1.392 (2) |
C2—C3 | 1.371 (3) | C13—C14 | 1.394 (2) |
C3—C4 | 1.391 (3) | C14—C15 | 1.396 (2) |
C3—H3 | 0.9500 | C14—H14 | 0.9500 |
C4—C5 | 1.502 (3) | C15—C16 | 1.379 (3) |
C5—H5A | 0.9800 | C15—H15 | 0.9500 |
C5—H5B | 0.9800 | C16—C17 | 1.381 (3) |
C5—H5C | 0.9800 | C16—H16 | 0.9500 |
N3—C7 | 1.3665 (19) | C17—C18 | 1.391 (2) |
N3—N4 | 1.3696 (18) | C17—H17 | 0.9500 |
N3—C11 | 1.4608 (18) | C18—H18 | 0.9500 |
N4—C9 | 1.335 (2) | C19—C20 | 1.387 (2) |
C6—C7 | 1.494 (2) | C19—C24 | 1.388 (2) |
C6—H6A | 0.9800 | C20—C21 | 1.390 (2) |
C6—H6B | 0.9800 | C20—H20 | 0.9500 |
C6—H6C | 0.9800 | C21—C22 | 1.374 (3) |
C7—C8 | 1.370 (2) | C21—H21 | 0.9500 |
C8—C9 | 1.402 (3) | C22—C23 | 1.375 (3) |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—C10 | 1.498 (2) | C23—C24 | 1.390 (3) |
C10—H10A | 0.9800 | C23—H23 | 0.9500 |
C10—H10B | 0.9800 | C24—H24 | 0.9500 |
| | | |
C2—N1—N2 | 112.34 (13) | N1—C11—N3 | 110.37 (11) |
C2—N1—C11 | 126.38 (14) | N1—C11—C12 | 112.28 (12) |
N2—N1—C11 | 120.79 (13) | N3—C11—C12 | 113.53 (12) |
C4—N2—N1 | 104.01 (15) | N1—C11—H11 | 106.7 |
C2—C1—H1A | 111.4 (15) | N3—C11—H11 | 106.7 |
C2—C1—H1B | 107.6 (15) | C12—C11—H11 | 106.7 |
H1A—C1—H1B | 109 (2) | O1—C12—C19 | 107.13 (12) |
C2—C1—H1C | 111.8 (14) | O1—C12—C13 | 110.43 (12) |
H1A—C1—H1C | 110 (2) | C19—C12—C13 | 111.02 (12) |
H1B—C1—H1C | 107 (2) | O1—C12—C11 | 109.95 (12) |
N1—C2—C3 | 105.51 (17) | C19—C12—C11 | 107.76 (11) |
N1—C2—C1 | 122.69 (16) | C13—C12—C11 | 110.47 (12) |
C3—C2—C1 | 131.79 (18) | C12—O1—H1D | 102.2 (14) |
C2—C3—C4 | 106.64 (16) | C18—C13—C14 | 118.08 (15) |
C2—C3—H3 | 126.7 | C18—C13—C12 | 118.52 (14) |
C4—C3—H3 | 126.7 | C14—C13—C12 | 123.37 (14) |
N2—C4—C3 | 111.46 (16) | C13—C14—C15 | 120.69 (16) |
N2—C4—C5 | 120.8 (2) | C13—C14—H14 | 119.7 |
C3—C4—C5 | 127.75 (18) | C15—C14—H14 | 119.7 |
C4—C5—H5A | 109.5 | C16—C15—C14 | 120.49 (18) |
C4—C5—H5B | 109.5 | C16—C15—H15 | 119.8 |
H5A—C5—H5B | 109.5 | C14—C15—H15 | 119.8 |
C4—C5—H5C | 109.5 | C15—C16—C17 | 119.31 (16) |
H5A—C5—H5C | 109.5 | C15—C16—H16 | 120.3 |
H5B—C5—H5C | 109.5 | C17—C16—H16 | 120.3 |
C7—N3—N4 | 112.26 (12) | C16—C17—C18 | 120.46 (17) |
C7—N3—C11 | 127.68 (13) | C16—C17—H17 | 119.8 |
N4—N3—C11 | 119.99 (12) | C18—C17—H17 | 119.8 |
C9—N4—N3 | 104.32 (13) | C17—C18—C13 | 120.96 (17) |
C7—C6—H6A | 109.5 | C17—C18—H18 | 119.5 |
C7—C6—H6B | 109.5 | C13—C18—H18 | 119.5 |
H6A—C6—H6B | 109.5 | C20—C19—C24 | 118.39 (15) |
C7—C6—H6C | 109.5 | C20—C19—C12 | 119.49 (14) |
H6A—C6—H6C | 109.5 | C24—C19—C12 | 122.08 (15) |
H6B—C6—H6C | 109.5 | C19—C20—C21 | 120.73 (17) |
N3—C7—C8 | 105.86 (14) | C19—C20—H20 | 119.6 |
N3—C7—C6 | 124.00 (14) | C21—C20—H20 | 119.6 |
C8—C7—C6 | 130.14 (15) | C22—C21—C20 | 120.45 (19) |
C7—C8—C9 | 106.24 (14) | C22—C21—H21 | 119.8 |
C7—C8—H8 | 126.9 | C20—C21—H21 | 119.8 |
C9—C8—H8 | 126.9 | C21—C22—C23 | 119.29 (17) |
N4—C9—C8 | 111.31 (15) | C21—C22—H22 | 120.4 |
N4—C9—C10 | 120.17 (17) | C23—C22—H22 | 120.4 |
C8—C9—C10 | 128.50 (16) | C22—C23—C24 | 120.74 (19) |
C9—C10—H10A | 109.5 | C22—C23—H23 | 119.6 |
C9—C10—H10B | 109.5 | C24—C23—H23 | 119.6 |
H10A—C10—H10B | 109.5 | C19—C24—C23 | 120.40 (18) |
C9—C10—H10C | 109.5 | C19—C24—H24 | 119.8 |
H10A—C10—H10C | 109.5 | C23—C24—H24 | 119.8 |
H10B—C10—H10C | 109.5 | | |
| | | |
C2—N1—N2—C4 | −1.35 (18) | N3—C11—C12—O1 | −61.42 (15) |
C11—N1—N2—C4 | −173.81 (13) | N1—C11—C12—C19 | −178.92 (12) |
N2—N1—C2—C3 | 1.62 (19) | N3—C11—C12—C19 | 55.02 (16) |
C11—N1—C2—C3 | 173.56 (14) | N1—C11—C12—C13 | −57.49 (16) |
N2—N1—C2—C1 | −177.62 (17) | N3—C11—C12—C13 | 176.45 (12) |
C11—N1—C2—C1 | −5.7 (3) | O1—C12—C13—C18 | 30.60 (18) |
N1—C2—C3—C4 | −1.2 (2) | C19—C12—C13—C18 | −88.06 (16) |
C1—C2—C3—C4 | 177.9 (2) | C11—C12—C13—C18 | 152.45 (13) |
N1—N2—C4—C3 | 0.55 (19) | O1—C12—C13—C14 | −151.43 (14) |
N1—N2—C4—C5 | 179.26 (16) | C19—C12—C13—C14 | 89.90 (17) |
C2—C3—C4—N2 | 0.4 (2) | C11—C12—C13—C14 | −29.59 (19) |
C2—C3—C4—C5 | −178.19 (18) | C18—C13—C14—C15 | −0.6 (2) |
C7—N3—N4—C9 | −0.04 (17) | C12—C13—C14—C15 | −178.61 (15) |
C11—N3—N4—C9 | 177.00 (13) | C13—C14—C15—C16 | 0.2 (3) |
N4—N3—C7—C8 | −0.20 (17) | C14—C15—C16—C17 | 0.6 (3) |
C11—N3—C7—C8 | −176.97 (14) | C15—C16—C17—C18 | −0.8 (3) |
N4—N3—C7—C6 | 179.93 (15) | C16—C17—C18—C13 | 0.4 (3) |
C11—N3—C7—C6 | 3.2 (2) | C14—C13—C18—C17 | 0.4 (2) |
N3—C7—C8—C9 | 0.35 (18) | C12—C13—C18—C17 | 178.45 (14) |
C6—C7—C8—C9 | −179.80 (17) | O1—C12—C19—C20 | 24.83 (19) |
N3—N4—C9—C8 | 0.27 (17) | C13—C12—C19—C20 | 145.47 (15) |
N3—N4—C9—C10 | −178.40 (14) | C11—C12—C19—C20 | −93.43 (17) |
C7—C8—C9—N4 | −0.40 (19) | O1—C12—C19—C24 | −157.47 (16) |
C7—C8—C9—C10 | 178.12 (16) | C13—C12—C19—C24 | −36.8 (2) |
C2—N1—C11—N3 | −77.25 (19) | C11—C12—C19—C24 | 84.27 (18) |
N2—N1—C11—N3 | 94.07 (15) | C24—C19—C20—C21 | 0.0 (3) |
C2—N1—C11—C12 | 154.99 (14) | C12—C19—C20—C21 | 177.78 (16) |
N2—N1—C11—C12 | −33.69 (18) | C19—C20—C21—C22 | 0.7 (3) |
C7—N3—C11—N1 | 126.12 (16) | C20—C21—C22—C23 | −0.8 (3) |
N4—N3—C11—N1 | −50.42 (17) | C21—C22—C23—C24 | 0.3 (3) |
C7—N3—C11—C12 | −106.81 (17) | C20—C19—C24—C23 | −0.5 (3) |
N4—N3—C11—C12 | 76.65 (16) | C12—C19—C24—C23 | −178.24 (18) |
N1—C11—C12—O1 | 64.65 (15) | C22—C23—C24—C19 | 0.4 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···N4i | 1.00 (3) | 2.57 (3) | 3.503 (3) | 155 (2) |
O1—H1D···N1 | 0.93 (2) | 2.47 (2) | 2.9669 (18) | 113.9 (17) |
O1—H1D···N2 | 0.93 (2) | 1.89 (2) | 2.7116 (18) | 147 (2) |
Symmetry code: (i) −x+3/2, y+1/2, z. |
cis-[2,2-Bis(3,5-dimethylpyrazolyl)-1,1-diphenylethanolato]chloridodioxidotungsten(VI) tetrahydrofuran monosolvate (2)
top
Crystal data top
[W(C24H25N4O)ClO2]·C4H8O | F(000) = 704 |
Mr = 708.88 | Dx = 1.724 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3157 (6) Å | Cell parameters from 12354 reflections |
b = 8.4063 (3) Å | θ = 2.7–27.8° |
c = 17.4678 (10) Å | µ = 4.37 mm−1 |
β = 93.222 (5)° | T = 153 K |
V = 1365.75 (13) Å3 | Prism, colourless |
Z = 2 | 0.25 × 0.18 × 0.10 mm |
Data collection top
Stoe IPDS 2T diffractometer | 5165 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 4924 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.019 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
rotation method scans | h = −12→12 |
Absorption correction: numerical (X-RED; Stoe & Cie, 2009) | k = −10→10 |
Tmin = 0.391, Tmax = 0.639 | l = −22→21 |
12354 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.024 | w = 1/[σ2(Fo2) + (0.0148P)2 + 4.1365P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.055 | (Δ/σ)max < 0.001 |
S = 1.08 | Δρmax = 0.94 e Å−3 |
5165 reflections | Δρmin = −1.06 e Å−3 |
348 parameters | Absolute structure: Refined as an inversion twin |
2 restraints | Absolute structure parameter: 0.489 (10) |
Primary atom site location: structure-invariant direct methods | |
Special details top
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 inversion twin The
structures were solved by direct methods with SHELXS-97 and refined by
full-matrix least-squares methods on F2 for all unique reflections
with SHELXL-2014 (Sheldrick, 2008). Crystal data, data collection and
structure refinement details are summarized in Table 1. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
W1 | 1.04108 (2) | 0.91051 (2) | 0.75170 (2) | 0.02602 (7) | |
Cl1 | 0.9829 (2) | 0.6550 (2) | 0.70373 (11) | 0.0384 (4) | |
O1 | 1.0519 (5) | 1.0754 (5) | 0.8271 (2) | 0.0230 (9) | |
O2 | 0.9488 (7) | 1.0125 (7) | 0.6767 (3) | 0.0415 (13) | |
O3 | 1.2171 (6) | 0.9119 (6) | 0.7263 (3) | 0.0364 (12) | |
N1 | 1.0583 (6) | 0.7973 (6) | 0.9298 (3) | 0.0210 (11) | |
N2 | 1.1142 (6) | 0.7653 (7) | 0.8599 (3) | 0.0252 (11) | |
C1 | 1.0580 (8) | 0.6951 (8) | 1.0644 (4) | 0.0299 (15) | |
H1A | 1.097589 | 0.790459 | 1.089940 | 0.045* | |
H1B | 1.093916 | 0.600175 | 1.091828 | 0.045* | |
H1C | 0.952780 | 0.697684 | 1.064274 | 0.045* | |
C2 | 1.1027 (7) | 0.6903 (7) | 0.9844 (4) | 0.0247 (13) | |
C3 | 1.1911 (7) | 0.5849 (8) | 0.9487 (4) | 0.0287 (14) | |
H3 | 1.239197 | 0.495853 | 0.971711 | 0.034* | |
C4 | 1.1965 (7) | 0.6339 (8) | 0.8722 (4) | 0.0297 (15) | |
C5 | 1.2790 (9) | 0.5623 (10) | 0.8109 (5) | 0.044 (2) | |
H5A | 1.225357 | 0.471908 | 0.788262 | 0.066* | |
H5B | 1.372457 | 0.525620 | 0.832552 | 0.066* | |
H5C | 1.293579 | 0.642069 | 0.771120 | 0.066* | |
N3 | 0.8289 (5) | 0.9045 (6) | 0.8927 (3) | 0.0204 (10) | |
N4 | 0.8279 (6) | 0.8789 (6) | 0.8150 (3) | 0.0227 (11) | |
C6 | 0.6630 (8) | 0.9110 (9) | 1.0021 (4) | 0.0325 (15) | |
H6A | 0.709143 | 0.822947 | 1.030853 | 0.049* | |
H6B | 0.558954 | 0.907368 | 1.007703 | 0.049* | |
H6C | 0.701219 | 1.012312 | 1.022199 | 0.049* | |
C7 | 0.6929 (7) | 0.8965 (7) | 0.9195 (4) | 0.0251 (13) | |
C8 | 0.6042 (7) | 0.8661 (8) | 0.8561 (4) | 0.0297 (15) | |
H8 | 0.502680 | 0.854436 | 0.855246 | 0.036* | |
C9 | 0.6890 (7) | 0.8550 (8) | 0.7926 (4) | 0.0292 (14) | |
C10 | 0.6416 (9) | 0.8240 (10) | 0.7106 (5) | 0.0424 (19) | |
H10A | 0.700576 | 0.886772 | 0.677059 | 0.064* | |
H10B | 0.540452 | 0.854172 | 0.701891 | 0.064* | |
H10C | 0.652895 | 0.710605 | 0.699322 | 0.064* | |
C11 | 0.9639 (6) | 0.9334 (7) | 0.9354 (4) | 0.0196 (12) | |
H11 | 0.943686 | 0.948290 | 0.990534 | 0.023* | |
C12 | 1.0347 (6) | 1.0887 (7) | 0.9066 (3) | 0.0194 (11) | |
C13 | 1.1824 (6) | 1.1213 (7) | 0.9481 (4) | 0.0205 (12) | |
C14 | 1.2010 (7) | 1.1228 (8) | 1.0278 (4) | 0.0247 (14) | |
H14 | 1.126007 | 1.085861 | 1.057938 | 0.030* | |
C15 | 1.3286 (7) | 1.1779 (9) | 1.0634 (4) | 0.0294 (15) | |
H15 | 1.340200 | 1.180257 | 1.117811 | 0.035* | |
C16 | 1.4393 (7) | 1.2297 (9) | 1.0193 (4) | 0.0308 (15) | |
H16 | 1.525014 | 1.271422 | 1.043636 | 0.037* | |
C17 | 1.4254 (7) | 1.2209 (8) | 0.9408 (4) | 0.0301 (15) | |
H17 | 1.502847 | 1.252174 | 0.911013 | 0.036* | |
C18 | 1.2979 (7) | 1.1661 (8) | 0.9048 (4) | 0.0256 (13) | |
H18 | 1.289046 | 1.158918 | 0.850413 | 0.031* | |
C19 | 0.9335 (6) | 1.2298 (7) | 0.9207 (4) | 0.0199 (12) | |
C20 | 0.8932 (7) | 1.3331 (8) | 0.8612 (4) | 0.0266 (13) | |
H20 | 0.926695 | 1.315324 | 0.811532 | 0.032* | |
C21 | 0.8047 (8) | 1.4616 (8) | 0.8736 (4) | 0.0318 (15) | |
H21 | 0.778288 | 1.531871 | 0.832634 | 0.038* | |
C22 | 0.7543 (7) | 1.4884 (8) | 0.9459 (5) | 0.0302 (15) | |
H22 | 0.691265 | 1.574893 | 0.953942 | 0.036* | |
C23 | 0.7960 (7) | 1.3892 (7) | 1.0056 (4) | 0.0262 (13) | |
H23 | 0.764144 | 1.409418 | 1.055429 | 0.031* | |
C24 | 0.8843 (7) | 1.2601 (8) | 0.9937 (4) | 0.0237 (13) | |
H24 | 0.911690 | 1.191508 | 1.035213 | 0.028* | |
O4 | 0.5979 (6) | 0.4017 (7) | 0.6188 (3) | 0.0466 (14) | |
C25 | 0.6737 (9) | 0.3274 (12) | 0.6824 (5) | 0.046 (2) | |
H25A | 0.739923 | 0.403989 | 0.709070 | 0.056* | |
H25B | 0.730398 | 0.236015 | 0.664967 | 0.056* | |
C26 | 0.5618 (10) | 0.2724 (10) | 0.7348 (5) | 0.045 (2) | |
H26A | 0.539426 | 0.356030 | 0.772203 | 0.054* | |
H26B | 0.592886 | 0.174829 | 0.762814 | 0.054* | |
C27 | 0.4333 (9) | 0.2396 (10) | 0.6792 (5) | 0.046 (2) | |
H27A | 0.439564 | 0.132565 | 0.655889 | 0.055* | |
H27B | 0.341570 | 0.248830 | 0.704791 | 0.055* | |
C28 | 0.4477 (9) | 0.3688 (10) | 0.6201 (5) | 0.0432 (19) | |
H28A | 0.409240 | 0.332480 | 0.569121 | 0.052* | |
H28B | 0.394489 | 0.465268 | 0.634551 | 0.052* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
W1 | 0.03934 (12) | 0.02519 (10) | 0.01392 (10) | −0.0007 (2) | 0.00483 (7) | −0.0025 (2) |
Cl1 | 0.0601 (12) | 0.0297 (8) | 0.0256 (9) | −0.0043 (8) | 0.0043 (8) | −0.0063 (7) |
O1 | 0.034 (2) | 0.023 (2) | 0.012 (2) | −0.001 (2) | 0.0021 (17) | −0.0003 (17) |
O2 | 0.058 (4) | 0.048 (3) | 0.019 (3) | −0.006 (3) | 0.006 (2) | 0.009 (2) |
O3 | 0.047 (3) | 0.039 (3) | 0.024 (3) | 0.001 (2) | 0.016 (2) | −0.008 (2) |
N1 | 0.029 (3) | 0.022 (2) | 0.013 (3) | 0.004 (2) | 0.005 (2) | −0.0001 (19) |
N2 | 0.033 (3) | 0.024 (3) | 0.019 (3) | 0.007 (2) | 0.003 (2) | −0.002 (2) |
C1 | 0.045 (4) | 0.027 (3) | 0.019 (3) | 0.007 (3) | 0.004 (3) | 0.006 (3) |
C2 | 0.029 (3) | 0.021 (3) | 0.024 (3) | −0.001 (3) | 0.000 (3) | 0.001 (2) |
C3 | 0.033 (3) | 0.023 (3) | 0.029 (4) | 0.010 (3) | −0.003 (3) | −0.002 (3) |
C4 | 0.029 (3) | 0.028 (3) | 0.032 (4) | 0.005 (3) | 0.002 (3) | −0.003 (3) |
C5 | 0.053 (5) | 0.041 (4) | 0.039 (5) | 0.022 (4) | 0.014 (4) | −0.003 (3) |
N3 | 0.028 (3) | 0.017 (2) | 0.017 (3) | 0.004 (2) | 0.0017 (19) | −0.001 (2) |
N4 | 0.030 (3) | 0.021 (3) | 0.017 (3) | 0.002 (2) | −0.001 (2) | −0.002 (2) |
C6 | 0.032 (3) | 0.033 (3) | 0.033 (4) | 0.001 (3) | 0.010 (3) | 0.000 (3) |
C7 | 0.028 (3) | 0.018 (3) | 0.030 (4) | 0.003 (3) | 0.008 (3) | 0.002 (3) |
C8 | 0.025 (3) | 0.028 (3) | 0.036 (4) | 0.002 (3) | −0.001 (3) | 0.002 (3) |
C9 | 0.033 (4) | 0.022 (3) | 0.031 (4) | 0.002 (3) | −0.009 (3) | 0.002 (3) |
C10 | 0.045 (5) | 0.044 (4) | 0.036 (5) | 0.004 (4) | −0.017 (3) | −0.006 (3) |
C11 | 0.024 (3) | 0.019 (3) | 0.017 (3) | 0.003 (2) | 0.003 (2) | −0.001 (2) |
C12 | 0.029 (3) | 0.018 (3) | 0.012 (3) | −0.001 (2) | 0.004 (2) | 0.001 (2) |
C13 | 0.024 (3) | 0.020 (3) | 0.018 (3) | 0.004 (2) | 0.004 (2) | 0.001 (2) |
C14 | 0.024 (3) | 0.035 (4) | 0.016 (3) | 0.000 (3) | 0.003 (2) | 0.001 (3) |
C15 | 0.024 (3) | 0.042 (4) | 0.022 (4) | 0.000 (3) | 0.004 (3) | −0.001 (3) |
C16 | 0.022 (3) | 0.036 (4) | 0.034 (4) | 0.001 (3) | 0.000 (3) | 0.001 (3) |
C17 | 0.023 (3) | 0.037 (4) | 0.031 (4) | −0.001 (3) | 0.008 (3) | 0.004 (3) |
C18 | 0.034 (3) | 0.027 (3) | 0.016 (3) | 0.004 (3) | 0.007 (3) | 0.000 (2) |
C19 | 0.024 (3) | 0.017 (3) | 0.019 (3) | −0.001 (2) | 0.001 (2) | −0.003 (2) |
C20 | 0.036 (4) | 0.023 (3) | 0.020 (3) | 0.002 (3) | −0.001 (3) | 0.004 (2) |
C21 | 0.037 (4) | 0.023 (3) | 0.035 (4) | 0.005 (3) | −0.005 (3) | 0.005 (3) |
C22 | 0.029 (3) | 0.018 (3) | 0.043 (4) | 0.004 (3) | 0.004 (3) | −0.004 (3) |
C23 | 0.027 (3) | 0.021 (3) | 0.031 (4) | 0.000 (2) | 0.005 (3) | −0.005 (3) |
C24 | 0.030 (3) | 0.020 (3) | 0.022 (3) | 0.002 (3) | 0.004 (3) | 0.000 (2) |
O4 | 0.048 (3) | 0.055 (3) | 0.037 (3) | −0.016 (3) | 0.001 (2) | 0.017 (3) |
C25 | 0.047 (5) | 0.058 (5) | 0.035 (5) | −0.001 (4) | −0.001 (4) | 0.004 (4) |
C26 | 0.054 (6) | 0.046 (4) | 0.034 (6) | 0.009 (4) | 0.002 (4) | 0.008 (3) |
C27 | 0.048 (5) | 0.043 (4) | 0.048 (5) | −0.006 (4) | 0.010 (4) | 0.003 (4) |
C28 | 0.042 (4) | 0.047 (5) | 0.040 (5) | 0.004 (4) | 0.001 (3) | 0.008 (4) |
Geometric parameters (Å, º) top
W1—O3 | 1.723 (5) | C11—H11 | 1.0000 |
W1—O2 | 1.751 (6) | C12—C13 | 1.543 (9) |
W1—O1 | 1.911 (4) | C12—C19 | 1.544 (8) |
W1—N2 | 2.320 (6) | C13—C14 | 1.393 (9) |
W1—N4 | 2.342 (6) | C13—C18 | 1.401 (8) |
W1—Cl1 | 2.3572 (18) | C14—C15 | 1.390 (9) |
O1—C12 | 1.410 (7) | C14—H14 | 0.9500 |
N1—C2 | 1.358 (8) | C15—C16 | 1.392 (9) |
N1—N2 | 1.380 (7) | C15—H15 | 0.9500 |
N1—C11 | 1.450 (7) | C16—C17 | 1.372 (10) |
N2—C4 | 1.356 (8) | C16—H16 | 0.9500 |
C1—C2 | 1.481 (9) | C17—C18 | 1.391 (10) |
C1—H1A | 0.9800 | C17—H17 | 0.9500 |
C1—H1B | 0.9800 | C18—H18 | 0.9500 |
C1—H1C | 0.9800 | C19—C20 | 1.390 (9) |
C2—C3 | 1.382 (9) | C19—C24 | 1.402 (8) |
C3—C4 | 1.401 (10) | C20—C21 | 1.384 (9) |
C3—H3 | 0.9500 | C20—H20 | 0.9500 |
C4—C5 | 1.481 (9) | C21—C22 | 1.389 (10) |
C5—H5A | 0.9800 | C21—H21 | 0.9500 |
C5—H5B | 0.9800 | C22—C23 | 1.375 (10) |
C5—H5C | 0.9800 | C22—H22 | 0.9500 |
N3—N4 | 1.374 (8) | C23—C24 | 1.385 (9) |
N3—C7 | 1.376 (8) | C23—H23 | 0.9500 |
N3—C11 | 1.446 (8) | C24—H24 | 0.9500 |
N4—C9 | 1.346 (9) | O4—C25 | 1.426 (10) |
C6—C7 | 1.491 (10) | O4—C28 | 1.428 (10) |
C6—H6A | 0.9800 | C25—C26 | 1.499 (11) |
C6—H6B | 0.9800 | C25—H25A | 0.9900 |
C6—H6C | 0.9800 | C25—H25B | 0.9900 |
C7—C8 | 1.369 (10) | C26—C27 | 1.524 (13) |
C8—C9 | 1.401 (10) | C26—H26A | 0.9900 |
C8—H8 | 0.9500 | C26—H26B | 0.9900 |
C9—C10 | 1.497 (10) | C27—C28 | 1.509 (11) |
C10—H10A | 0.9800 | C27—H27A | 0.9900 |
C10—H10B | 0.9800 | C27—H27B | 0.9900 |
C10—H10C | 0.9800 | C28—H28A | 0.9900 |
C11—C12 | 1.559 (8) | C28—H28B | 0.9900 |
| | | |
O3—W1—O2 | 103.8 (3) | N1—C11—C12 | 111.7 (5) |
O3—W1—O1 | 99.1 (2) | N3—C11—H11 | 108.2 |
O2—W1—O1 | 99.5 (3) | N1—C11—H11 | 108.2 |
O3—W1—N2 | 88.5 (2) | C12—C11—H11 | 108.2 |
O2—W1—N2 | 167.7 (2) | O1—C12—C13 | 109.2 (5) |
O1—W1—N2 | 79.52 (19) | O1—C12—C19 | 108.8 (5) |
O3—W1—N4 | 165.3 (2) | C13—C12—C19 | 109.0 (5) |
O2—W1—N4 | 90.9 (2) | O1—C12—C11 | 108.9 (5) |
O1—W1—N4 | 76.70 (19) | C13—C12—C11 | 112.3 (5) |
N2—W1—N4 | 76.9 (2) | C19—C12—C11 | 108.6 (5) |
O3—W1—Cl1 | 96.76 (19) | C14—C13—C18 | 118.8 (6) |
O2—W1—Cl1 | 95.0 (2) | C14—C13—C12 | 121.9 (5) |
O1—W1—Cl1 | 155.24 (14) | C18—C13—C12 | 119.0 (6) |
N2—W1—Cl1 | 82.04 (15) | C15—C14—C13 | 120.3 (6) |
N4—W1—Cl1 | 83.14 (13) | C15—C14—H14 | 119.8 |
C12—O1—W1 | 137.0 (4) | C13—C14—H14 | 119.8 |
C2—N1—N2 | 112.2 (5) | C14—C15—C16 | 119.9 (7) |
C2—N1—C11 | 129.6 (5) | C14—C15—H15 | 120.1 |
N2—N1—C11 | 118.3 (5) | C16—C15—H15 | 120.1 |
C4—N2—N1 | 104.9 (5) | C17—C16—C15 | 120.3 (6) |
C4—N2—W1 | 134.1 (4) | C17—C16—H16 | 119.8 |
N1—N2—W1 | 120.7 (4) | C15—C16—H16 | 119.8 |
C2—C1—H1A | 109.5 | C16—C17—C18 | 120.0 (6) |
C2—C1—H1B | 109.5 | C16—C17—H17 | 120.0 |
H1A—C1—H1B | 109.5 | C18—C17—H17 | 120.0 |
C2—C1—H1C | 109.5 | C17—C18—C13 | 120.4 (6) |
H1A—C1—H1C | 109.5 | C17—C18—H18 | 119.8 |
H1B—C1—H1C | 109.5 | C13—C18—H18 | 119.8 |
N1—C2—C3 | 105.9 (6) | C20—C19—C24 | 118.6 (6) |
N1—C2—C1 | 123.6 (6) | C20—C19—C12 | 120.1 (5) |
C3—C2—C1 | 130.5 (6) | C24—C19—C12 | 121.2 (5) |
C2—C3—C4 | 107.2 (6) | C21—C20—C19 | 120.5 (6) |
C2—C3—H3 | 126.4 | C21—C20—H20 | 119.7 |
C4—C3—H3 | 126.4 | C19—C20—H20 | 119.7 |
N2—C4—C3 | 109.9 (6) | C20—C21—C22 | 120.3 (7) |
N2—C4—C5 | 121.9 (7) | C20—C21—H21 | 119.9 |
C3—C4—C5 | 128.2 (6) | C22—C21—H21 | 119.9 |
C4—C5—H5A | 109.5 | C23—C22—C21 | 119.7 (6) |
C4—C5—H5B | 109.5 | C23—C22—H22 | 120.1 |
H5A—C5—H5B | 109.5 | C21—C22—H22 | 120.1 |
C4—C5—H5C | 109.5 | C22—C23—C24 | 120.4 (6) |
H5A—C5—H5C | 109.5 | C22—C23—H23 | 119.8 |
H5B—C5—H5C | 109.5 | C24—C23—H23 | 119.8 |
N4—N3—C7 | 111.9 (5) | C23—C24—C19 | 120.4 (6) |
N4—N3—C11 | 119.5 (5) | C23—C24—H24 | 119.8 |
C7—N3—C11 | 128.6 (5) | C19—C24—H24 | 119.8 |
C9—N4—N3 | 105.3 (6) | C25—O4—C28 | 110.2 (6) |
C9—N4—W1 | 134.9 (5) | O4—C25—C26 | 106.2 (7) |
N3—N4—W1 | 119.4 (4) | O4—C25—H25A | 110.5 |
C7—C6—H6A | 109.5 | C26—C25—H25A | 110.5 |
C7—C6—H6B | 109.5 | O4—C25—H25B | 110.5 |
H6A—C6—H6B | 109.5 | C26—C25—H25B | 110.5 |
C7—C6—H6C | 109.5 | H25A—C25—H25B | 108.7 |
H6A—C6—H6C | 109.5 | C25—C26—C27 | 102.4 (7) |
H6B—C6—H6C | 109.5 | C25—C26—H26A | 111.3 |
C8—C7—N3 | 105.1 (6) | C27—C26—H26A | 111.3 |
C8—C7—C6 | 131.4 (6) | C25—C26—H26B | 111.3 |
N3—C7—C6 | 123.4 (6) | C27—C26—H26B | 111.3 |
C7—C8—C9 | 108.1 (6) | H26A—C26—H26B | 109.2 |
C7—C8—H8 | 125.9 | C28—C27—C26 | 102.0 (7) |
C9—C8—H8 | 125.9 | C28—C27—H27A | 111.4 |
N4—C9—C8 | 109.6 (6) | C26—C27—H27A | 111.4 |
N4—C9—C10 | 122.1 (7) | C28—C27—H27B | 111.4 |
C8—C9—C10 | 128.3 (7) | C26—C27—H27B | 111.4 |
C9—C10—H10A | 109.5 | H27A—C27—H27B | 109.2 |
C9—C10—H10B | 109.5 | O4—C28—C27 | 105.9 (7) |
H10A—C10—H10B | 109.5 | O4—C28—H28A | 110.5 |
C9—C10—H10C | 109.5 | C27—C28—H28A | 110.5 |
H10A—C10—H10C | 109.5 | O4—C28—H28B | 110.5 |
H10B—C10—H10C | 109.5 | C27—C28—H28B | 110.5 |
N3—C11—N1 | 110.3 (5) | H28A—C28—H28B | 108.7 |
N3—C11—C12 | 110.3 (5) | | |
| | | |
C2—N1—N2—C4 | −0.2 (7) | W1—O1—C12—C19 | −130.9 (5) |
C11—N1—N2—C4 | −180.0 (5) | W1—O1—C12—C11 | −12.7 (8) |
C2—N1—N2—W1 | 173.8 (4) | N3—C11—C12—O1 | −56.6 (6) |
C11—N1—N2—W1 | −5.9 (7) | N1—C11—C12—O1 | 66.4 (6) |
N2—N1—C2—C3 | 0.1 (8) | N3—C11—C12—C13 | −177.7 (5) |
C11—N1—C2—C3 | 179.8 (6) | N1—C11—C12—C13 | −54.7 (6) |
N2—N1—C2—C1 | −179.3 (6) | N3—C11—C12—C19 | 61.8 (6) |
C11—N1—C2—C1 | 0.4 (11) | N1—C11—C12—C19 | −175.3 (5) |
N1—C2—C3—C4 | 0.0 (8) | O1—C12—C13—C14 | −172.9 (5) |
C1—C2—C3—C4 | 179.4 (7) | C19—C12—C13—C14 | 68.4 (7) |
N1—N2—C4—C3 | 0.2 (7) | C11—C12—C13—C14 | −51.9 (7) |
W1—N2—C4—C3 | −172.6 (5) | O1—C12—C13—C18 | 13.5 (7) |
N1—N2—C4—C5 | −178.7 (7) | C19—C12—C13—C18 | −105.2 (6) |
W1—N2—C4—C5 | 8.5 (11) | C11—C12—C13—C18 | 134.5 (6) |
C2—C3—C4—N2 | −0.2 (8) | C18—C13—C14—C15 | 4.3 (10) |
C2—C3—C4—C5 | 178.6 (8) | C12—C13—C14—C15 | −169.3 (6) |
C7—N3—N4—C9 | 0.2 (7) | C13—C14—C15—C16 | −1.0 (11) |
C11—N3—N4—C9 | 179.6 (5) | C14—C15—C16—C17 | −2.5 (11) |
C7—N3—N4—W1 | 173.9 (4) | C15—C16—C17—C18 | 2.7 (11) |
C11—N3—N4—W1 | −6.7 (7) | C16—C17—C18—C13 | 0.7 (10) |
N4—N3—C7—C8 | −0.4 (7) | C14—C13—C18—C17 | −4.2 (9) |
C11—N3—C7—C8 | −179.7 (6) | C12—C13—C18—C17 | 169.6 (6) |
N4—N3—C7—C6 | 176.6 (6) | O1—C12—C19—C20 | −9.5 (8) |
C11—N3—C7—C6 | −2.7 (10) | C13—C12—C19—C20 | 109.5 (6) |
N3—C7—C8—C9 | 0.5 (7) | C11—C12—C19—C20 | −127.9 (6) |
C6—C7—C8—C9 | −176.2 (7) | O1—C12—C19—C24 | 172.8 (5) |
N3—N4—C9—C8 | 0.1 (7) | C13—C12—C19—C24 | −68.2 (7) |
W1—N4—C9—C8 | −172.2 (4) | C11—C12—C19—C24 | 54.4 (8) |
N3—N4—C9—C10 | 179.5 (6) | C24—C19—C20—C21 | −0.9 (10) |
W1—N4—C9—C10 | 7.2 (10) | C12—C19—C20—C21 | −178.8 (6) |
C7—C8—C9—N4 | −0.4 (8) | C19—C20—C21—C22 | −0.4 (11) |
C7—C8—C9—C10 | −179.7 (7) | C20—C21—C22—C23 | 1.9 (11) |
N4—N3—C11—N1 | −61.5 (7) | C21—C22—C23—C24 | −2.0 (10) |
C7—N3—C11—N1 | 117.8 (6) | C22—C23—C24—C19 | 0.7 (10) |
N4—N3—C11—C12 | 62.4 (6) | C20—C19—C24—C23 | 0.8 (10) |
C7—N3—C11—C12 | −118.4 (6) | C12—C19—C24—C23 | 178.6 (6) |
C2—N1—C11—N3 | −110.3 (7) | C28—O4—C25—C26 | −11.7 (10) |
N2—N1—C11—N3 | 69.3 (7) | O4—C25—C26—C27 | 29.8 (9) |
C2—N1—C11—C12 | 126.7 (7) | C25—C26—C27—C28 | −35.7 (9) |
N2—N1—C11—C12 | −53.7 (7) | C25—O4—C28—C27 | −11.7 (9) |
W1—O1—C12—C13 | 110.3 (6) | C26—C27—C28—O4 | 29.6 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5C···O3 | 0.98 | 2.49 | 3.325 (10) | 143 |
C10—H10A···O2 | 0.98 | 2.54 | 3.353 (11) | 140 |
C15—H15···O3i | 0.95 | 2.40 | 3.174 (9) | 139 |
C6—H6A···O4ii | 0.98 | 2.68 | 3.402 (10) | 131 |
C23—H23···O4i | 0.95 | 2.52 | 3.289 (8) | 138 |
Symmetry codes: (i) x, −y+2, z+1/2; (ii) x, −y+1, z+1/2. |