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4,4′-{9,9′-Spirobi[10
H-acridine]-10,10′-diyl}dibenzoic acid (
L, C
29H
26N
2O
4) was designed and synthesized as a new donor–acceptor motif molecule. Due to the large dihedral angle between the planes of the carboxyphenyl group and the spiroacridine moiety,
L possess thermally activated delayed fluorescence (TADF). By applying
L as a ligand and using Cd as a metal connector, we synthesized the coordination polymer
catena-poly[hemi-μ-aqua-aqua(μ
3-4,4′-{9,9′-spirobi[10
H-acridine]-10,10′-diyl}dibenzoato)cadmium(II)], [Cd(C
29H
24N
2O
4)(H
2O)
1.5]
n, (
I). X-ray crystallographic analysis revealed that this coordination polymer exhibits one-dimensional chains constructed from molecular twist-ring moieties, with Cd
2O
11 clusters as the connection nodes. The stacking pattern of the two-dimensional network was formed by C—H
π interactions in the solid state. Similar to
L, (
I) presents a sky-blue TADF emission, together with a photoluminescence quantum yield (PLQY) of 40%. It is worth noting that the photocatalytic activity toward the generation of singlet oxygen of this coordination polymer is confirmed.
Supporting information
CCDC references: 1854555; 1841420
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
4,4'-{9,9'-Spirobi[10
H-acridine]-10,10'-diyl}dibenzoic acid (L)
top
Crystal data top
C39H26N2O4 | Z = 2 |
Mr = 586.62 | F(000) = 612 |
Triclinic, P1 | Dx = 1.009 Mg m−3 |
a = 12.6717 (10) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 13.0727 (9) Å | Cell parameters from 3153 reflections |
c = 13.9254 (11) Å | θ = 7.0–70.6° |
α = 65.029 (7)° | µ = 0.53 mm−1 |
β = 75.294 (7)° | T = 294 K |
γ = 68.420 (7)° | Block, clear light colourless |
V = 1931.2 (3) Å3 | 0.27 × 0.13 × 0.09 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Eos detector | 7278 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 4599 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.023 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 70.9°, θmin = 3.5° |
ω scans | h = −15→14 |
Absorption correction: multi-scan (CrysAlis PRO (Rigaku OD, 2015) | k = −16→8 |
Tmin = 0.848, Tmax = 1.000 | l = −16→14 |
13193 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.200 | w = 1/[σ2(Fo2) + (0.0968P)2 + 0.174P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
7278 reflections | Δρmax = 0.21 e Å−3 |
409 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.0008 (3) |
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. 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 > 2sigma(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 | |
C22 | 0.53570 (17) | 0.67838 (18) | 0.48653 (15) | 0.0406 (4) | |
N1 | 0.65184 (15) | 0.62169 (18) | 0.49259 (14) | 0.0519 (5) | |
C27 | 0.46400 (17) | 0.70674 (17) | 0.57183 (15) | 0.0383 (4) | |
C1 | 0.50747 (17) | 0.67556 (17) | 0.67685 (15) | 0.0387 (4) | |
N2 | 0.33683 (17) | 0.72755 (17) | 0.85048 (15) | 0.0564 (5) | |
C9 | 0.37209 (19) | 0.61385 (19) | 0.84749 (16) | 0.0465 (5) | |
O3 | 0.94039 (18) | 0.41989 (18) | 0.12965 (16) | 0.0796 (6) | |
H3 | 0.9798 | 0.4149 | 0.0742 | 0.119* | |
C15 | 0.63745 (18) | 0.62050 (18) | 0.67021 (16) | 0.0432 (5) | |
C20 | 0.70306 (17) | 0.59262 (18) | 0.58282 (16) | 0.0446 (5) | |
C7 | 0.39304 (19) | 0.81187 (19) | 0.78121 (16) | 0.0477 (5) | |
C23 | 0.48805 (19) | 0.7091 (2) | 0.39345 (17) | 0.0497 (5) | |
H23 | 0.5351 | 0.6909 | 0.3360 | 0.060* | |
C26 | 0.34906 (18) | 0.76437 (19) | 0.56126 (16) | 0.0459 (5) | |
H26 | 0.3014 | 0.7838 | 0.6179 | 0.055* | |
C2 | 0.47551 (18) | 0.78941 (18) | 0.69887 (15) | 0.0413 (4) | |
O4 | 0.95665 (18) | 0.60151 (19) | 0.05478 (16) | 0.0843 (6) | |
C25 | 0.3024 (2) | 0.7942 (2) | 0.47000 (18) | 0.0535 (6) | |
H25 | 0.2249 | 0.8329 | 0.4652 | 0.064* | |
C14 | 0.45200 (18) | 0.58593 (18) | 0.76623 (15) | 0.0418 (5) | |
C13 | 0.4815 (2) | 0.47302 (19) | 0.76557 (17) | 0.0494 (5) | |
H13 | 0.5339 | 0.4544 | 0.7107 | 0.059* | |
C28 | 0.72263 (18) | 0.5949 (2) | 0.40229 (17) | 0.0493 (5) | |
C19 | 0.8203 (2) | 0.5349 (2) | 0.5862 (2) | 0.0615 (6) | |
H19 | 0.8642 | 0.5150 | 0.5286 | 0.074* | |
C24 | 0.3736 (2) | 0.7652 (2) | 0.38586 (18) | 0.0527 (5) | |
H24 | 0.3438 | 0.7839 | 0.3240 | 0.063* | |
C3 | 0.5279 (2) | 0.8758 (2) | 0.63173 (18) | 0.0532 (5) | |
H3A | 0.5817 | 0.8621 | 0.5756 | 0.064* | |
C31 | 0.85364 (18) | 0.5457 (2) | 0.22652 (17) | 0.0515 (5) | |
C10 | 0.3252 (2) | 0.5263 (2) | 0.92660 (18) | 0.0584 (6) | |
H10 | 0.2716 | 0.5444 | 0.9811 | 0.070* | |
C32 | 0.7999 (2) | 0.4666 (2) | 0.30380 (19) | 0.0581 (6) | |
H32 | 0.8080 | 0.3961 | 0.2971 | 0.070* | |
C30 | 0.8421 (2) | 0.6502 (2) | 0.23725 (18) | 0.0549 (6) | |
H30 | 0.8778 | 0.7041 | 0.1849 | 0.066* | |
C11 | 0.3568 (2) | 0.4155 (2) | 0.92503 (19) | 0.0626 (6) | |
H11 | 0.3255 | 0.3586 | 0.9785 | 0.075* | |
C12 | 0.4357 (2) | 0.3875 (2) | 0.84348 (19) | 0.0575 (6) | |
H12 | 0.4573 | 0.3122 | 0.8415 | 0.069* | |
C6 | 0.3661 (2) | 0.9199 (2) | 0.7938 (2) | 0.0638 (7) | |
H6 | 0.3100 | 0.9364 | 0.8475 | 0.077* | |
C29 | 0.7778 (2) | 0.6742 (2) | 0.32570 (18) | 0.0542 (6) | |
H29 | 0.7715 | 0.7433 | 0.3338 | 0.065* | |
C4 | 0.5026 (2) | 0.9808 (2) | 0.6457 (2) | 0.0636 (7) | |
H4 | 0.5395 | 1.0368 | 0.6004 | 0.076* | |
C16 | 0.6916 (2) | 0.5923 (2) | 0.75704 (18) | 0.0572 (6) | |
H16 | 0.6483 | 0.6112 | 0.8154 | 0.069* | |
C34 | 0.92137 (19) | 0.5231 (2) | 0.13005 (19) | 0.0559 (6) | |
C37 | 0.2650 (2) | 0.7485 (2) | 0.94296 (18) | 0.0552 (6) | |
C40 | 0.1335 (2) | 0.7950 (2) | 1.11868 (19) | 0.0604 (6) | |
O1 | −0.0419 (2) | 0.8608 (3) | 1.21770 (19) | 0.1048 (8) | |
O2 | 0.1199 (2) | 0.8055 (3) | 1.28629 (18) | 0.1035 (8) | |
H2 | 0.0760 | 0.8200 | 1.3365 | 0.155* | |
C38 | 0.1499 (2) | 0.8020 (3) | 0.9411 (2) | 0.0690 (7) | |
H38 | 0.1160 | 0.8221 | 0.8811 | 0.083* | |
C42 | 0.3145 (2) | 0.7142 (3) | 1.0333 (2) | 0.0693 (7) | |
H42 | 0.3922 | 0.6750 | 1.0351 | 0.083* | |
C33 | 0.7338 (2) | 0.4919 (2) | 0.3915 (2) | 0.0604 (6) | |
H33 | 0.6970 | 0.4388 | 0.4431 | 0.073* | |
C5 | 0.4219 (3) | 1.0013 (2) | 0.7276 (2) | 0.0685 (7) | |
H5 | 0.4048 | 1.0716 | 0.7383 | 0.082* | |
C39 | 0.0842 (2) | 0.8258 (3) | 1.0301 (2) | 0.0718 (7) | |
H39 | 0.0060 | 0.8630 | 1.0292 | 0.086* | |
C17 | 0.8071 (2) | 0.5374 (3) | 0.7595 (2) | 0.0723 (8) | |
H17 | 0.8417 | 0.5207 | 0.8181 | 0.087* | |
C41 | 0.2486 (2) | 0.7381 (3) | 1.1212 (2) | 0.0712 (8) | |
H41 | 0.2821 | 0.7157 | 1.1820 | 0.085* | |
C18 | 0.8712 (2) | 0.5073 (3) | 0.6737 (2) | 0.0729 (8) | |
H18 | 0.9490 | 0.4682 | 0.6752 | 0.087* | |
C43 | 0.0611 (3) | 0.8235 (3) | 1.2125 (2) | 0.0708 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C22 | 0.0393 (11) | 0.0459 (11) | 0.0368 (10) | −0.0105 (9) | −0.0003 (8) | −0.0197 (9) |
N1 | 0.0432 (10) | 0.0695 (12) | 0.0438 (10) | −0.0056 (9) | −0.0009 (8) | −0.0333 (9) |
C27 | 0.0435 (11) | 0.0391 (10) | 0.0333 (9) | −0.0133 (9) | 0.0006 (8) | −0.0162 (8) |
C1 | 0.0412 (11) | 0.0439 (11) | 0.0319 (9) | −0.0131 (9) | 0.0021 (8) | −0.0179 (8) |
N2 | 0.0663 (13) | 0.0571 (12) | 0.0463 (10) | −0.0238 (10) | 0.0177 (9) | −0.0284 (9) |
C9 | 0.0507 (12) | 0.0519 (13) | 0.0370 (10) | −0.0163 (10) | 0.0024 (9) | −0.0198 (9) |
O3 | 0.0809 (14) | 0.0932 (14) | 0.0723 (13) | −0.0251 (11) | 0.0247 (10) | −0.0569 (11) |
C15 | 0.0455 (11) | 0.0464 (11) | 0.0385 (10) | −0.0137 (9) | −0.0023 (8) | −0.0176 (9) |
C20 | 0.0399 (11) | 0.0477 (12) | 0.0432 (11) | −0.0077 (9) | −0.0031 (9) | −0.0196 (9) |
C7 | 0.0533 (13) | 0.0498 (12) | 0.0413 (11) | −0.0161 (10) | 0.0025 (9) | −0.0217 (9) |
C23 | 0.0541 (13) | 0.0592 (14) | 0.0391 (11) | −0.0133 (11) | −0.0013 (9) | −0.0263 (10) |
C26 | 0.0430 (11) | 0.0512 (12) | 0.0421 (11) | −0.0107 (10) | −0.0003 (9) | −0.0213 (9) |
C2 | 0.0471 (11) | 0.0443 (11) | 0.0359 (10) | −0.0160 (9) | −0.0003 (8) | −0.0185 (8) |
O4 | 0.0943 (15) | 0.0992 (15) | 0.0657 (12) | −0.0410 (12) | 0.0334 (11) | −0.0496 (12) |
C25 | 0.0468 (12) | 0.0559 (14) | 0.0564 (13) | −0.0082 (10) | −0.0103 (10) | −0.0228 (11) |
C14 | 0.0466 (11) | 0.0484 (12) | 0.0338 (10) | −0.0191 (9) | −0.0015 (8) | −0.0156 (9) |
C13 | 0.0563 (13) | 0.0507 (12) | 0.0422 (11) | −0.0153 (10) | −0.0006 (9) | −0.0211 (10) |
C28 | 0.0425 (11) | 0.0632 (14) | 0.0426 (11) | −0.0089 (10) | 0.0042 (9) | −0.0307 (10) |
C19 | 0.0437 (12) | 0.0769 (17) | 0.0554 (14) | −0.0052 (12) | −0.0025 (10) | −0.0290 (13) |
C24 | 0.0564 (14) | 0.0601 (14) | 0.0439 (12) | −0.0145 (11) | −0.0132 (10) | −0.0192 (10) |
C3 | 0.0597 (14) | 0.0579 (14) | 0.0469 (12) | −0.0256 (11) | 0.0057 (10) | −0.0234 (10) |
C31 | 0.0403 (11) | 0.0700 (15) | 0.0475 (12) | −0.0103 (10) | 0.0029 (9) | −0.0342 (11) |
C10 | 0.0673 (15) | 0.0665 (15) | 0.0408 (12) | −0.0301 (13) | 0.0118 (10) | −0.0205 (11) |
C32 | 0.0599 (15) | 0.0623 (15) | 0.0580 (14) | −0.0174 (12) | 0.0118 (11) | −0.0386 (12) |
C30 | 0.0527 (13) | 0.0643 (15) | 0.0487 (12) | −0.0199 (11) | 0.0076 (10) | −0.0271 (11) |
C11 | 0.0809 (18) | 0.0594 (15) | 0.0471 (13) | −0.0351 (13) | −0.0001 (12) | −0.0113 (11) |
C12 | 0.0728 (16) | 0.0491 (13) | 0.0524 (13) | −0.0222 (12) | −0.0068 (12) | −0.0170 (11) |
C6 | 0.0734 (17) | 0.0624 (15) | 0.0577 (14) | −0.0188 (13) | 0.0101 (12) | −0.0351 (12) |
C29 | 0.0552 (13) | 0.0572 (14) | 0.0548 (13) | −0.0131 (11) | 0.0043 (10) | −0.0340 (11) |
C4 | 0.0776 (18) | 0.0572 (15) | 0.0621 (15) | −0.0324 (13) | 0.0017 (13) | −0.0226 (12) |
C16 | 0.0524 (13) | 0.0767 (16) | 0.0428 (12) | −0.0199 (12) | −0.0049 (10) | −0.0220 (11) |
C34 | 0.0430 (12) | 0.0755 (17) | 0.0540 (14) | −0.0114 (12) | 0.0037 (10) | −0.0388 (13) |
C37 | 0.0600 (14) | 0.0596 (14) | 0.0451 (12) | −0.0199 (11) | 0.0133 (10) | −0.0273 (11) |
C40 | 0.0633 (16) | 0.0671 (16) | 0.0524 (14) | −0.0214 (13) | 0.0144 (11) | −0.0336 (12) |
O1 | 0.0699 (14) | 0.162 (2) | 0.1005 (17) | −0.0309 (14) | 0.0290 (12) | −0.0896 (17) |
O2 | 0.0859 (15) | 0.156 (2) | 0.0783 (15) | −0.0162 (15) | 0.0114 (12) | −0.0807 (16) |
C38 | 0.0582 (16) | 0.092 (2) | 0.0551 (15) | −0.0154 (14) | 0.0010 (12) | −0.0356 (14) |
C42 | 0.0551 (15) | 0.092 (2) | 0.0585 (15) | −0.0068 (14) | 0.0045 (12) | −0.0447 (15) |
C33 | 0.0639 (15) | 0.0640 (15) | 0.0558 (14) | −0.0224 (12) | 0.0117 (11) | −0.0319 (12) |
C5 | 0.0866 (19) | 0.0527 (15) | 0.0735 (17) | −0.0216 (14) | −0.0025 (14) | −0.0329 (13) |
C39 | 0.0541 (15) | 0.086 (2) | 0.0682 (17) | −0.0118 (14) | 0.0093 (13) | −0.0385 (15) |
C17 | 0.0613 (16) | 0.095 (2) | 0.0553 (15) | −0.0190 (15) | −0.0188 (12) | −0.0197 (14) |
C41 | 0.0684 (17) | 0.090 (2) | 0.0545 (15) | −0.0095 (15) | 0.0016 (12) | −0.0429 (14) |
C18 | 0.0443 (14) | 0.091 (2) | 0.0727 (17) | −0.0075 (13) | −0.0134 (12) | −0.0269 (15) |
C43 | 0.0710 (18) | 0.0831 (19) | 0.0630 (16) | −0.0261 (15) | 0.0185 (13) | −0.0434 (15) |
Geometric parameters (Å, º) top
C22—N1 | 1.389 (3) | C3—C4 | 1.376 (3) |
C22—C27 | 1.396 (3) | C31—C32 | 1.378 (3) |
C22—C23 | 1.409 (3) | C31—C30 | 1.387 (3) |
N1—C20 | 1.405 (3) | C31—C34 | 1.481 (3) |
N1—C28 | 1.441 (2) | C10—H10 | 0.9300 |
C27—C1 | 1.533 (3) | C10—C11 | 1.361 (3) |
C27—C26 | 1.385 (3) | C32—H32 | 0.9300 |
C1—C15 | 1.532 (3) | C32—C33 | 1.385 (3) |
C1—C2 | 1.534 (3) | C30—H30 | 0.9300 |
C1—C14 | 1.532 (3) | C30—C29 | 1.382 (3) |
N2—C9 | 1.402 (3) | C11—H11 | 0.9300 |
N2—C7 | 1.409 (3) | C11—C12 | 1.389 (3) |
N2—C37 | 1.443 (3) | C12—H12 | 0.9300 |
C9—C14 | 1.391 (3) | C6—H6 | 0.9300 |
C9—C10 | 1.407 (3) | C6—C5 | 1.369 (4) |
O3—H3 | 0.8200 | C29—H29 | 0.9300 |
O3—C34 | 1.282 (3) | C4—H4 | 0.9300 |
C15—C20 | 1.394 (3) | C4—C5 | 1.373 (4) |
C15—C16 | 1.388 (3) | C16—H16 | 0.9300 |
C20—C19 | 1.400 (3) | C16—C17 | 1.376 (4) |
C7—C2 | 1.394 (3) | C37—C38 | 1.368 (3) |
C7—C6 | 1.402 (3) | C37—C42 | 1.376 (3) |
C23—H23 | 0.9300 | C40—C39 | 1.363 (4) |
C23—C24 | 1.372 (3) | C40—C41 | 1.374 (4) |
C26—H26 | 0.9300 | C40—C43 | 1.496 (3) |
C26—C25 | 1.382 (3) | O1—C43 | 1.208 (4) |
C2—C3 | 1.391 (3) | O2—H2 | 0.8200 |
O4—C34 | 1.242 (3) | O2—C43 | 1.312 (4) |
C25—H25 | 0.9300 | C38—H38 | 0.9300 |
C25—C24 | 1.385 (3) | C38—C39 | 1.393 (3) |
C14—C13 | 1.386 (3) | C42—H42 | 0.9300 |
C13—H13 | 0.9300 | C42—C41 | 1.380 (3) |
C13—C12 | 1.377 (3) | C33—H33 | 0.9300 |
C28—C29 | 1.386 (3) | C5—H5 | 0.9300 |
C28—C33 | 1.370 (3) | C39—H39 | 0.9300 |
C19—H19 | 0.9300 | C17—H17 | 0.9300 |
C19—C18 | 1.374 (4) | C17—C18 | 1.382 (4) |
C24—H24 | 0.9300 | C41—H41 | 0.9300 |
C3—H3A | 0.9300 | C18—H18 | 0.9300 |
| | | |
N1—C22—C27 | 120.94 (17) | C9—C10—H10 | 119.3 |
N1—C22—C23 | 120.41 (17) | C11—C10—C9 | 121.3 (2) |
C27—C22—C23 | 118.65 (19) | C11—C10—H10 | 119.3 |
C22—N1—C20 | 122.09 (16) | C31—C32—H32 | 120.0 |
C22—N1—C28 | 118.98 (17) | C31—C32—C33 | 120.0 (2) |
C20—N1—C28 | 118.90 (17) | C33—C32—H32 | 120.0 |
C22—C27—C1 | 122.51 (18) | C31—C30—H30 | 120.0 |
C26—C27—C22 | 118.63 (17) | C29—C30—C31 | 120.0 (2) |
C26—C27—C1 | 118.86 (17) | C29—C30—H30 | 120.0 |
C27—C1—C2 | 108.34 (16) | C10—C11—H11 | 120.0 |
C15—C1—C27 | 111.04 (15) | C10—C11—C12 | 120.0 (2) |
C15—C1—C2 | 109.17 (16) | C12—C11—H11 | 120.0 |
C15—C1—C14 | 108.60 (16) | C13—C12—C11 | 119.0 (2) |
C14—C1—C27 | 108.74 (15) | C13—C12—H12 | 120.5 |
C14—C1—C2 | 110.95 (15) | C11—C12—H12 | 120.5 |
C9—N2—C7 | 121.08 (17) | C7—C6—H6 | 119.8 |
C9—N2—C37 | 119.08 (18) | C5—C6—C7 | 120.5 (2) |
C7—N2—C37 | 117.60 (18) | C5—C6—H6 | 119.8 |
N2—C9—C10 | 120.03 (19) | C28—C29—H29 | 120.1 |
C14—C9—N2 | 121.06 (19) | C30—C29—C28 | 119.8 (2) |
C14—C9—C10 | 118.9 (2) | C30—C29—H29 | 120.1 |
C34—O3—H3 | 109.5 | C3—C4—H4 | 120.6 |
C20—C15—C1 | 122.88 (17) | C5—C4—C3 | 118.8 (2) |
C16—C15—C1 | 118.51 (18) | C5—C4—H4 | 120.6 |
C16—C15—C20 | 118.6 (2) | C15—C16—H16 | 118.9 |
C15—C20—N1 | 120.28 (18) | C17—C16—C15 | 122.1 (2) |
C15—C20—C19 | 119.3 (2) | C17—C16—H16 | 118.9 |
C19—C20—N1 | 120.45 (19) | O3—C34—C31 | 116.4 (2) |
C2—C7—N2 | 120.49 (19) | O4—C34—O3 | 123.2 (2) |
C2—C7—C6 | 119.2 (2) | O4—C34—C31 | 120.4 (2) |
C6—C7—N2 | 120.4 (2) | C38—C37—N2 | 120.8 (2) |
C22—C23—H23 | 119.4 | C38—C37—C42 | 120.4 (2) |
C24—C23—C22 | 121.28 (19) | C42—C37—N2 | 118.8 (2) |
C24—C23—H23 | 119.4 | C39—C40—C41 | 120.0 (2) |
C27—C26—H26 | 118.7 | C39—C40—C43 | 119.4 (2) |
C25—C26—C27 | 122.65 (19) | C41—C40—C43 | 120.6 (2) |
C25—C26—H26 | 118.7 | C43—O2—H2 | 109.5 |
C7—C2—C1 | 122.71 (18) | C37—C38—H38 | 120.4 |
C3—C2—C1 | 118.77 (18) | C37—C38—C39 | 119.1 (2) |
C3—C2—C7 | 118.47 (19) | C39—C38—H38 | 120.4 |
C26—C25—H25 | 120.7 | C37—C42—H42 | 120.0 |
C26—C25—C24 | 118.5 (2) | C37—C42—C41 | 120.0 (2) |
C24—C25—H25 | 120.7 | C41—C42—H42 | 120.0 |
C9—C14—C1 | 122.51 (18) | C28—C33—C32 | 120.3 (2) |
C13—C14—C1 | 118.85 (18) | C28—C33—H33 | 119.9 |
C13—C14—C9 | 118.64 (19) | C32—C33—H33 | 119.9 |
C14—C13—H13 | 118.9 | C6—C5—C4 | 121.0 (2) |
C12—C13—C14 | 122.2 (2) | C6—C5—H5 | 119.5 |
C12—C13—H13 | 118.9 | C4—C5—H5 | 119.5 |
C29—C28—N1 | 120.0 (2) | C40—C39—C38 | 120.6 (2) |
C33—C28—N1 | 119.9 (2) | C40—C39—H39 | 119.7 |
C33—C28—C29 | 120.1 (2) | C38—C39—H39 | 119.7 |
C20—C19—H19 | 119.6 | C16—C17—H17 | 120.5 |
C18—C19—C20 | 120.8 (2) | C16—C17—C18 | 119.0 (2) |
C18—C19—H19 | 119.6 | C18—C17—H17 | 120.5 |
C23—C24—C25 | 120.23 (19) | C40—C41—C42 | 119.9 (2) |
C23—C24—H24 | 119.9 | C40—C41—H41 | 120.1 |
C25—C24—H24 | 119.9 | C42—C41—H41 | 120.1 |
C2—C3—H3A | 118.9 | C19—C18—C17 | 120.2 (2) |
C4—C3—C2 | 122.1 (2) | C19—C18—H18 | 119.9 |
C4—C3—H3A | 118.9 | C17—C18—H18 | 119.9 |
C32—C31—C30 | 119.8 (2) | O1—C43—C40 | 122.1 (3) |
C32—C31—C34 | 121.2 (2) | O1—C43—O2 | 124.1 (2) |
C30—C31—C34 | 119.0 (2) | O2—C43—C40 | 113.8 (3) |
| | | |
C22—N1—C20—C15 | 0.0 (3) | C7—C6—C5—C4 | 2.0 (4) |
C22—N1—C20—C19 | 179.7 (2) | C23—C22—N1—C20 | 178.2 (2) |
C22—N1—C28—C29 | 92.4 (3) | C23—C22—N1—C28 | 0.0 (3) |
C22—N1—C28—C33 | −86.6 (3) | C23—C22—C27—C1 | 179.15 (18) |
C22—C27—C1—C15 | 4.6 (3) | C23—C22—C27—C26 | −0.3 (3) |
C22—C27—C1—C2 | 124.5 (2) | C26—C27—C1—C15 | −175.95 (17) |
C22—C27—C1—C14 | −114.8 (2) | C26—C27—C1—C2 | −56.1 (2) |
C22—C27—C26—C25 | 0.4 (3) | C26—C27—C1—C14 | 64.6 (2) |
C22—C23—C24—C25 | 0.7 (4) | C26—C25—C24—C23 | −0.6 (3) |
N1—C22—C27—C1 | −1.2 (3) | C2—C1—C15—C20 | −125.5 (2) |
N1—C22—C27—C26 | 179.33 (19) | C2—C1—C15—C16 | 57.5 (2) |
N1—C22—C23—C24 | −179.9 (2) | C2—C1—C14—C9 | 7.7 (3) |
N1—C20—C19—C18 | 179.3 (2) | C2—C1—C14—C13 | −173.01 (18) |
N1—C28—C29—C30 | −177.6 (2) | C2—C7—C6—C5 | −1.5 (4) |
N1—C28—C33—C32 | 178.7 (2) | C2—C3—C4—C5 | −1.0 (4) |
C27—C22—N1—C20 | −1.4 (3) | C14—C1—C15—C20 | 113.4 (2) |
C27—C22—N1—C28 | −179.57 (19) | C14—C1—C15—C16 | −63.6 (2) |
C27—C22—C23—C24 | −0.3 (3) | C14—C1—C2—C7 | −9.0 (3) |
C27—C1—C15—C20 | −6.1 (3) | C14—C1—C2—C3 | 173.32 (19) |
C27—C1—C15—C16 | 176.87 (19) | C14—C9—C10—C11 | 0.2 (4) |
C27—C1—C2—C7 | 110.3 (2) | C14—C13—C12—C11 | 0.5 (4) |
C27—C1—C2—C3 | −67.4 (2) | C28—N1—C20—C15 | 178.1 (2) |
C27—C1—C14—C9 | −111.3 (2) | C28—N1—C20—C19 | −2.2 (3) |
C27—C1—C14—C13 | 67.9 (2) | C3—C4—C5—C6 | −0.8 (4) |
C27—C26—C25—C24 | 0.0 (3) | C31—C32—C33—C28 | −0.7 (4) |
C1—C27—C26—C25 | −179.0 (2) | C31—C30—C29—C28 | −1.5 (4) |
C1—C15—C20—N1 | 4.1 (3) | C10—C9—C14—C1 | 180.0 (2) |
C1—C15—C20—C19 | −175.6 (2) | C10—C9—C14—C13 | 0.7 (3) |
C1—C15—C16—C17 | 176.8 (2) | C10—C11—C12—C13 | 0.5 (4) |
C1—C2—C3—C4 | 179.2 (2) | C32—C31—C30—C29 | 0.6 (4) |
C1—C14—C13—C12 | 179.6 (2) | C32—C31—C34—O3 | −9.5 (3) |
N2—C9—C14—C1 | 1.0 (3) | C32—C31—C34—O4 | 170.5 (2) |
N2—C9—C14—C13 | −178.3 (2) | C30—C31—C32—C33 | 0.5 (4) |
N2—C9—C10—C11 | 179.2 (2) | C30—C31—C34—O3 | 172.2 (2) |
N2—C7—C2—C1 | 1.7 (3) | C30—C31—C34—O4 | −7.8 (3) |
N2—C7—C2—C3 | 179.3 (2) | C6—C7—C2—C1 | −177.9 (2) |
N2—C7—C6—C5 | 179.0 (2) | C6—C7—C2—C3 | −0.2 (3) |
N2—C37—C38—C39 | −177.0 (2) | C29—C28—C33—C32 | −0.2 (4) |
N2—C37—C42—C41 | 177.1 (2) | C16—C15—C20—N1 | −178.8 (2) |
C9—N2—C7—C2 | 8.3 (3) | C16—C15—C20—C19 | 1.5 (3) |
C9—N2—C7—C6 | −172.2 (2) | C16—C17—C18—C19 | 1.7 (5) |
C9—N2—C37—C38 | −101.3 (3) | C34—C31—C32—C33 | −177.8 (2) |
C9—N2—C37—C42 | 78.9 (3) | C34—C31—C30—C29 | 178.9 (2) |
C9—C14—C13—C12 | −1.1 (3) | C37—N2—C9—C14 | −172.3 (2) |
C9—C10—C11—C12 | −0.8 (4) | C37—N2—C9—C10 | 8.8 (3) |
C15—C1—C2—C7 | −128.7 (2) | C37—N2—C7—C2 | 171.1 (2) |
C15—C1—C2—C3 | 53.7 (2) | C37—N2—C7—C6 | −9.3 (3) |
C15—C1—C14—C9 | 127.7 (2) | C37—C38—C39—C40 | −0.8 (4) |
C15—C1—C14—C13 | −53.0 (2) | C37—C42—C41—C40 | 0.7 (5) |
C15—C20—C19—C18 | −1.0 (4) | C38—C37—C42—C41 | −2.7 (4) |
C15—C16—C17—C18 | −1.2 (4) | C42—C37—C38—C39 | 2.8 (4) |
C20—N1—C28—C29 | −85.8 (3) | C33—C28—C29—C30 | 1.3 (4) |
C20—N1—C28—C33 | 95.2 (3) | C39—C40—C41—C42 | 1.2 (4) |
C20—C15—C16—C17 | −0.4 (4) | C39—C40—C43—O1 | 8.7 (4) |
C20—C19—C18—C17 | −0.7 (5) | C39—C40—C43—O2 | −170.6 (3) |
C7—N2—C9—C14 | −9.7 (3) | C41—C40—C39—C38 | −1.2 (4) |
C7—N2—C9—C10 | 171.3 (2) | C41—C40—C43—O1 | −171.2 (3) |
C7—N2—C37—C38 | 95.5 (3) | C41—C40—C43—O2 | 9.5 (4) |
C7—N2—C37—C42 | −84.3 (3) | C43—C40—C39—C38 | 179.0 (3) |
C7—C2—C3—C4 | 1.5 (3) | C43—C40—C41—C42 | −178.9 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O4i | 0.82 | 1.84 | 2.648 (2) | 168 |
C4—H4···Cg1ii | 0.93 | 2.90 | 3.7568 (3) | 154 |
C33—H33···Cg1iii | 0.93 | 2.85 | 3.7156 (3) | 156 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1. |
catena-Poly[hemi-µ-aqua-aqua(µ
3-4,4'-{9,9'-spirobi[10
H-\
acridine]-10,10'-diyl}dibenzoato)cadmium(II)] (I)
top
Crystal data top
[Cd(C39H24N2O4)(H2O)1.5] | F(000) = 2936 |
Mr = 724.03 | Dx = 1.006 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
a = 27.4361 (19) Å | Cell parameters from 4113 reflections |
b = 9.0861 (9) Å | θ = 7.0–70.7° |
c = 40.473 (2) Å | µ = 3.94 mm−1 |
β = 108.581 (7)° | T = 293 K |
V = 9563.5 (13) Å3 | Block, colourless |
Z = 8 | 0.29 × 0.23 × 0.14 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 8499 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 5609 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.057 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 71.3°, θmin = 3.4° |
ω scans | h = −30→33 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −8→10 |
Tmin = 0.660, Tmax = 1.000 | l = −48→49 |
16822 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.227 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.1147P)2 + 0.6298P] where P = (Fo2 + 2Fc2)/3 |
8499 reflections | (Δ/σ)max = 0.001 |
429 parameters | Δρmax = 0.62 e Å−3 |
0 restraints | Δρmin = −1.22 e Å−3 |
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. 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 > 2sigma(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 | Occ. (<1) |
C1 | 0.5584 (3) | 0.7956 (8) | 0.29867 (12) | 0.106 (2) | |
C2 | 0.5682 (2) | 0.6943 (6) | 0.32910 (13) | 0.0791 (14) | |
C3 | 0.5327 (2) | 0.6755 (6) | 0.34653 (12) | 0.0755 (13) | |
H3 | 0.5011 | 0.7231 | 0.3388 | 0.091* | |
C4 | 0.5444 (2) | 0.5851 (6) | 0.37567 (12) | 0.0694 (12) | |
H4 | 0.5204 | 0.5716 | 0.3872 | 0.083* | |
C5 | 0.5911 (2) | 0.5156 (5) | 0.38766 (12) | 0.0625 (11) | |
C6 | 0.6267 (2) | 0.5341 (7) | 0.37075 (16) | 0.0885 (17) | |
H6 | 0.6580 | 0.4851 | 0.3787 | 0.106* | |
C7 | 0.6162 (2) | 0.6263 (7) | 0.34158 (13) | 0.0885 (17) | |
H7 | 0.6409 | 0.6419 | 0.3307 | 0.106* | |
C8 | 0.62467 (15) | 0.4923 (4) | 0.45093 (11) | 0.0497 (9) | |
C9 | 0.64304 (16) | 0.6383 (5) | 0.45344 (12) | 0.0586 (10) | |
H9 | 0.6404 | 0.6909 | 0.4332 | 0.070* | |
C10 | 0.66477 (16) | 0.7036 (5) | 0.48533 (12) | 0.0608 (10) | |
H10 | 0.6765 | 0.8001 | 0.4865 | 0.073* | |
C11 | 0.66945 (15) | 0.6279 (5) | 0.51564 (13) | 0.0607 (11) | |
H11 | 0.6846 | 0.6718 | 0.5372 | 0.073* | |
C12 | 0.65121 (16) | 0.4854 (4) | 0.51333 (12) | 0.0525 (9) | |
H12 | 0.6537 | 0.4349 | 0.5338 | 0.063* | |
C13 | 0.62916 (13) | 0.4142 (4) | 0.48160 (10) | 0.0439 (8) | |
C14 | 0.60750 (13) | 0.2580 (4) | 0.48100 (10) | 0.0458 (8) | |
C15 | 0.59464 (13) | 0.1907 (4) | 0.44474 (10) | 0.0486 (8) | |
C16 | 0.59139 (16) | 0.2758 (5) | 0.41552 (10) | 0.0558 (9) | |
C17 | 0.5745 (2) | 0.2097 (6) | 0.38240 (12) | 0.0726 (13) | |
H17 | 0.5712 | 0.2664 | 0.3627 | 0.087* | |
C18 | 0.5627 (2) | 0.0610 (6) | 0.37884 (14) | 0.0752 (14) | |
H18 | 0.5518 | 0.0181 | 0.3568 | 0.090* | |
C19 | 0.5674 (2) | −0.0239 (5) | 0.40832 (14) | 0.0717 (13) | |
H19 | 0.5598 | −0.1239 | 0.4062 | 0.086* | |
C20 | 0.58333 (18) | 0.0416 (5) | 0.44068 (13) | 0.0612 (11) | |
H20 | 0.5866 | −0.0155 | 0.4603 | 0.073* | |
C21 | 0.64751 (13) | 0.1647 (4) | 0.50724 (10) | 0.0459 (8) | |
C22 | 0.69388 (14) | 0.1350 (4) | 0.50128 (12) | 0.0538 (9) | |
H22 | 0.6992 | 0.1715 | 0.4812 | 0.065* | |
C23 | 0.73240 (16) | 0.0523 (5) | 0.52445 (14) | 0.0623 (11) | |
H23 | 0.7633 | 0.0353 | 0.5202 | 0.075* | |
C24 | 0.72417 (18) | −0.0034 (5) | 0.55340 (15) | 0.0652 (12) | |
H24 | 0.7495 | −0.0608 | 0.5687 | 0.078* | |
C25 | 0.6791 (2) | 0.0231 (6) | 0.56065 (14) | 0.0674 (12) | |
H25 | 0.6746 | −0.0150 | 0.5808 | 0.081* | |
C26 | 0.63992 (15) | 0.1085 (5) | 0.53733 (11) | 0.0543 (9) | |
C27 | 0.55297 (16) | 0.2083 (5) | 0.52074 (12) | 0.0587 (10) | |
C28 | 0.50587 (18) | 0.2225 (6) | 0.52781 (14) | 0.0727 (13) | |
H28 | 0.5027 | 0.1855 | 0.5485 | 0.087* | |
C29 | 0.46532 (16) | 0.2903 (6) | 0.50434 (15) | 0.0762 (14) | |
H29 | 0.4341 | 0.2956 | 0.5087 | 0.091* | |
C30 | 0.46954 (17) | 0.3506 (6) | 0.47460 (14) | 0.0712 (13) | |
H30 | 0.4420 | 0.4008 | 0.4593 | 0.085* | |
C31 | 0.51546 (15) | 0.3359 (5) | 0.46752 (12) | 0.0598 (10) | |
H31 | 0.5179 | 0.3736 | 0.4467 | 0.072* | |
C32 | 0.55763 (13) | 0.2673 (4) | 0.49024 (10) | 0.0498 (9) | |
C33 | 0.59179 (17) | 0.1076 (6) | 0.57899 (12) | 0.0630 (11) | |
C34 | 0.5714 (2) | −0.0190 (6) | 0.58660 (14) | 0.0733 (14) | |
H34 | 0.5596 | −0.0905 | 0.5695 | 0.088* | |
C35 | 0.5681 (2) | −0.0430 (6) | 0.61983 (15) | 0.0792 (14) | |
H35 | 0.5540 | −0.1301 | 0.6248 | 0.095* | |
C36 | 0.5853 (2) | 0.0607 (6) | 0.64484 (13) | 0.0730 (13) | |
C37 | 0.6055 (3) | 0.1877 (8) | 0.63714 (16) | 0.108 (2) | |
H37 | 0.6173 | 0.2590 | 0.6543 | 0.130* | |
C38 | 0.6088 (3) | 0.2130 (7) | 0.60375 (16) | 0.103 (2) | |
H38 | 0.6225 | 0.3006 | 0.5987 | 0.123* | |
C39 | 0.5798 (3) | 0.0383 (8) | 0.68039 (15) | 0.0851 (16) | |
Cd1 | 0.559298 (17) | 0.02398 (6) | 0.741018 (9) | 0.0866 (2) | |
N1 | 0.60290 (16) | 0.4276 (4) | 0.41861 (9) | 0.0632 (9) | |
N2 | 0.59425 (14) | 0.1350 (5) | 0.54462 (10) | 0.0691 (10) | |
O1 | 0.56019 (18) | −0.0740 (5) | 0.68698 (10) | 0.0923 (11) | |
O2 | 0.5947 (2) | 0.1424 (7) | 0.70227 (12) | 0.1301 (19) | |
O3 | 0.5889 (2) | 0.8127 (7) | 0.28346 (12) | 0.142 (2) | |
O4 | 0.5179 (3) | 0.8665 (8) | 0.29007 (13) | 0.154 (3) | |
O5 | 0.5000 | −0.1318 (9) | 0.7500 | 0.208 (6) | |
H5A | 0.4849 | −0.1937 | 0.7298 | 0.250* | 0.50 |
H5B | 0.5151 | −0.1937 | 0.7702 | 0.250* | 0.50 |
O6 | 0.6240 (4) | −0.1355 (13) | 0.76825 (19) | 0.303 (7) | |
H6A | 0.6368 | −0.1803 | 0.7512 | 0.454* | |
H6B | 0.6512 | −0.0817 | 0.7847 | 0.454* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.156 (6) | 0.118 (5) | 0.029 (2) | 0.017 (5) | 0.010 (3) | 0.011 (3) |
C2 | 0.101 (4) | 0.077 (3) | 0.055 (3) | 0.015 (3) | 0.019 (3) | 0.010 (2) |
C3 | 0.089 (3) | 0.076 (3) | 0.057 (3) | 0.020 (3) | 0.016 (2) | −0.002 (2) |
C4 | 0.083 (3) | 0.069 (3) | 0.057 (3) | 0.005 (3) | 0.022 (2) | 0.007 (2) |
C5 | 0.080 (3) | 0.061 (2) | 0.048 (2) | 0.003 (2) | 0.022 (2) | 0.0097 (19) |
C6 | 0.089 (4) | 0.106 (4) | 0.074 (4) | 0.020 (3) | 0.031 (3) | 0.035 (3) |
C7 | 0.084 (3) | 0.127 (5) | 0.061 (3) | 0.009 (3) | 0.031 (3) | 0.028 (3) |
C8 | 0.049 (2) | 0.051 (2) | 0.052 (2) | 0.0016 (16) | 0.0190 (17) | −0.0002 (17) |
C9 | 0.063 (2) | 0.051 (2) | 0.067 (3) | 0.0035 (19) | 0.028 (2) | 0.007 (2) |
C10 | 0.058 (2) | 0.052 (2) | 0.074 (3) | −0.0039 (19) | 0.024 (2) | −0.003 (2) |
C11 | 0.051 (2) | 0.056 (2) | 0.070 (3) | −0.0012 (19) | 0.0121 (19) | −0.016 (2) |
C12 | 0.052 (2) | 0.054 (2) | 0.053 (2) | 0.0049 (17) | 0.0183 (18) | −0.0005 (17) |
C13 | 0.0413 (17) | 0.0458 (19) | 0.048 (2) | 0.0083 (15) | 0.0182 (15) | 0.0018 (16) |
C14 | 0.0426 (18) | 0.049 (2) | 0.0471 (19) | 0.0039 (16) | 0.0162 (15) | 0.0051 (16) |
C15 | 0.0447 (18) | 0.051 (2) | 0.051 (2) | 0.0044 (17) | 0.0167 (16) | −0.0011 (17) |
C16 | 0.061 (2) | 0.057 (2) | 0.049 (2) | 0.0056 (19) | 0.0172 (18) | −0.0061 (18) |
C17 | 0.090 (3) | 0.075 (3) | 0.050 (2) | 0.006 (3) | 0.018 (2) | −0.006 (2) |
C18 | 0.084 (3) | 0.073 (3) | 0.063 (3) | 0.002 (3) | 0.015 (2) | −0.020 (3) |
C19 | 0.090 (3) | 0.058 (3) | 0.064 (3) | −0.004 (2) | 0.019 (3) | −0.017 (2) |
C20 | 0.065 (2) | 0.051 (2) | 0.069 (3) | −0.002 (2) | 0.023 (2) | −0.005 (2) |
C21 | 0.0434 (18) | 0.0446 (19) | 0.053 (2) | 0.0035 (16) | 0.0192 (15) | 0.0040 (16) |
C22 | 0.048 (2) | 0.052 (2) | 0.065 (2) | 0.0042 (18) | 0.0235 (18) | 0.0027 (19) |
C23 | 0.045 (2) | 0.065 (3) | 0.082 (3) | 0.011 (2) | 0.026 (2) | 0.001 (2) |
C24 | 0.059 (2) | 0.060 (3) | 0.074 (3) | 0.007 (2) | 0.018 (2) | 0.003 (2) |
C25 | 0.070 (3) | 0.080 (3) | 0.055 (3) | 0.006 (2) | 0.023 (2) | 0.016 (2) |
C26 | 0.051 (2) | 0.064 (2) | 0.052 (2) | 0.0036 (19) | 0.0216 (17) | 0.0052 (19) |
C27 | 0.050 (2) | 0.066 (3) | 0.068 (3) | 0.003 (2) | 0.0304 (19) | 0.001 (2) |
C28 | 0.066 (3) | 0.080 (3) | 0.086 (3) | 0.015 (2) | 0.044 (3) | 0.014 (3) |
C29 | 0.042 (2) | 0.089 (3) | 0.107 (4) | 0.008 (2) | 0.037 (2) | −0.002 (3) |
C30 | 0.050 (2) | 0.077 (3) | 0.087 (3) | 0.014 (2) | 0.023 (2) | 0.002 (3) |
C31 | 0.051 (2) | 0.063 (2) | 0.067 (3) | 0.012 (2) | 0.0212 (19) | 0.004 (2) |
C32 | 0.0418 (18) | 0.050 (2) | 0.061 (2) | 0.0042 (16) | 0.0221 (17) | −0.0007 (18) |
C33 | 0.061 (2) | 0.082 (3) | 0.055 (2) | 0.000 (2) | 0.029 (2) | −0.002 (2) |
C34 | 0.091 (4) | 0.086 (3) | 0.051 (3) | −0.008 (3) | 0.034 (3) | −0.002 (2) |
C35 | 0.095 (4) | 0.085 (3) | 0.072 (3) | −0.009 (3) | 0.047 (3) | 0.000 (3) |
C36 | 0.083 (3) | 0.091 (3) | 0.050 (3) | −0.010 (3) | 0.030 (2) | −0.012 (2) |
C37 | 0.152 (6) | 0.114 (5) | 0.074 (4) | −0.039 (5) | 0.059 (4) | −0.030 (4) |
C38 | 0.140 (6) | 0.093 (4) | 0.095 (4) | −0.030 (4) | 0.066 (4) | −0.012 (4) |
C39 | 0.095 (4) | 0.111 (5) | 0.055 (3) | −0.001 (3) | 0.032 (3) | −0.010 (3) |
Cd1 | 0.1117 (4) | 0.1101 (4) | 0.0434 (3) | 0.0093 (2) | 0.0321 (2) | −0.00852 (17) |
N1 | 0.090 (3) | 0.0519 (19) | 0.0467 (19) | 0.0004 (19) | 0.0209 (18) | 0.0005 (16) |
N2 | 0.063 (2) | 0.094 (3) | 0.061 (2) | 0.018 (2) | 0.0351 (18) | 0.017 (2) |
O1 | 0.122 (3) | 0.110 (3) | 0.057 (2) | −0.004 (3) | 0.045 (2) | −0.001 (2) |
O2 | 0.175 (5) | 0.158 (5) | 0.077 (3) | −0.048 (4) | 0.068 (3) | −0.040 (3) |
O3 | 0.175 (5) | 0.179 (5) | 0.068 (3) | 0.011 (4) | 0.033 (3) | 0.067 (3) |
O4 | 0.190 (6) | 0.185 (6) | 0.071 (3) | 0.079 (5) | 0.020 (3) | 0.048 (4) |
O5 | 0.330 (14) | 0.099 (5) | 0.302 (14) | 0.000 | 0.250 (13) | 0.000 |
O6 | 0.367 (13) | 0.334 (13) | 0.121 (6) | 0.229 (12) | −0.044 (7) | −0.045 (7) |
Geometric parameters (Å, º) top
C1—C2 | 1.491 (7) | C23—C24 | 1.360 (7) |
C1—O3 | 1.198 (9) | C24—H24 | 0.9300 |
C1—O4 | 1.233 (9) | C24—C25 | 1.379 (7) |
C2—C3 | 1.385 (7) | C25—H25 | 0.9300 |
C2—C7 | 1.394 (8) | C25—C26 | 1.416 (6) |
C3—H3 | 0.9300 | C26—N2 | 1.397 (5) |
C3—C4 | 1.388 (7) | C27—C28 | 1.416 (5) |
C4—H4 | 0.9300 | C27—C32 | 1.388 (6) |
C4—C5 | 1.371 (7) | C27—N2 | 1.401 (6) |
C5—C6 | 1.369 (8) | C28—H28 | 0.9300 |
C5—N1 | 1.434 (6) | C28—C29 | 1.359 (7) |
C6—H6 | 0.9300 | C29—H29 | 0.9300 |
C6—C7 | 1.400 (7) | C29—C30 | 1.360 (7) |
C7—H7 | 0.9300 | C30—H30 | 0.9300 |
C8—C9 | 1.411 (6) | C30—C31 | 1.385 (6) |
C8—C13 | 1.401 (6) | C31—H31 | 0.9300 |
C8—N1 | 1.384 (6) | C31—C32 | 1.377 (5) |
C9—H9 | 0.9300 | C33—C34 | 1.356 (7) |
C9—C10 | 1.372 (6) | C33—C38 | 1.357 (7) |
C10—H10 | 0.9300 | C33—N2 | 1.436 (5) |
C10—C11 | 1.376 (6) | C34—H34 | 0.9300 |
C11—H11 | 0.9300 | C34—C35 | 1.394 (7) |
C11—C12 | 1.380 (6) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C35—C36 | 1.353 (7) |
C12—C13 | 1.392 (6) | C36—C37 | 1.358 (8) |
C13—C14 | 1.536 (5) | C36—C39 | 1.508 (7) |
C14—C15 | 1.524 (5) | C37—H37 | 0.9300 |
C14—C21 | 1.519 (5) | C37—C38 | 1.403 (8) |
C14—C32 | 1.531 (5) | C38—H38 | 0.9300 |
C15—C16 | 1.392 (6) | C39—Cd1 | 2.689 (6) |
C15—C20 | 1.387 (6) | C39—O1 | 1.222 (7) |
C16—C17 | 1.406 (6) | C39—O2 | 1.271 (7) |
C16—N1 | 1.411 (6) | Cd1—O1 | 2.369 (4) |
C17—H17 | 0.9300 | Cd1—O2 | 2.352 (5) |
C17—C18 | 1.386 (7) | Cd1—O3i | 2.219 (4) |
C18—H18 | 0.9300 | Cd1—O4ii | 2.316 (6) |
C18—C19 | 1.392 (8) | Cd1—O5 | 2.272 (5) |
C19—H19 | 0.9300 | Cd1—O6 | 2.284 (7) |
C19—C20 | 1.377 (7) | O3—Cd1iii | 2.219 (4) |
C20—H20 | 0.9300 | O4—Cd1ii | 2.316 (6) |
C21—C22 | 1.395 (5) | O5—Cd1iv | 2.272 (5) |
C21—C26 | 1.396 (5) | O5—H5A | 0.9700 |
C22—H22 | 0.9300 | O5—H5B | 0.9700 |
C22—C23 | 1.389 (6) | O6—H6A | 0.9600 |
C23—H23 | 0.9300 | O6—H6B | 0.9600 |
| | | |
O3—C1—C2 | 122.1 (7) | C32—C27—N2 | 120.9 (3) |
O3—C1—O4 | 120.1 (6) | N2—C27—C28 | 119.5 (4) |
O4—C1—C2 | 117.8 (7) | C27—C28—H28 | 120.1 |
C3—C2—C1 | 121.7 (6) | C29—C28—C27 | 119.8 (4) |
C3—C2—C7 | 119.8 (5) | C29—C28—H28 | 120.1 |
C7—C2—C1 | 118.4 (6) | C28—C29—H29 | 119.4 |
C2—C3—H3 | 120.1 | C28—C29—C30 | 121.3 (4) |
C2—C3—C4 | 119.7 (5) | C30—C29—H29 | 119.4 |
C4—C3—H3 | 120.1 | C29—C30—H30 | 120.5 |
C3—C4—H4 | 119.6 | C29—C30—C31 | 118.9 (4) |
C5—C4—C3 | 120.7 (5) | C31—C30—H30 | 120.5 |
C5—C4—H4 | 119.6 | C30—C31—H31 | 118.9 |
C4—C5—N1 | 119.4 (4) | C32—C31—C30 | 122.1 (4) |
C6—C5—C4 | 120.1 (4) | C32—C31—H31 | 118.9 |
C6—C5—N1 | 120.5 (4) | C27—C32—C14 | 122.6 (3) |
C5—C6—H6 | 119.8 | C31—C32—C14 | 119.2 (4) |
C5—C6—C7 | 120.4 (5) | C31—C32—C27 | 118.2 (3) |
C7—C6—H6 | 119.8 | C34—C33—C38 | 120.0 (5) |
C2—C7—C6 | 119.2 (5) | C34—C33—N2 | 121.1 (5) |
C2—C7—H7 | 120.4 | C38—C33—N2 | 118.8 (5) |
C6—C7—H7 | 120.4 | C33—C34—H34 | 119.6 |
C13—C8—C9 | 118.9 (4) | C33—C34—C35 | 120.7 (5) |
N1—C8—C9 | 120.3 (4) | C35—C34—H34 | 119.6 |
N1—C8—C13 | 120.8 (4) | C34—C35—H35 | 120.1 |
C8—C9—H9 | 119.6 | C36—C35—C34 | 119.8 (5) |
C10—C9—C8 | 120.8 (4) | C36—C35—H35 | 120.1 |
C10—C9—H9 | 119.6 | C35—C36—C37 | 119.4 (5) |
C9—C10—H10 | 119.6 | C35—C36—C39 | 120.1 (5) |
C9—C10—C11 | 120.8 (4) | C37—C36—C39 | 120.4 (5) |
C11—C10—H10 | 119.6 | C36—C37—H37 | 119.4 |
C10—C11—H11 | 120.7 | C36—C37—C38 | 121.2 (6) |
C10—C11—C12 | 118.7 (4) | C38—C37—H37 | 119.4 |
C12—C11—H11 | 120.7 | C33—C38—C37 | 118.9 (6) |
C11—C12—H12 | 118.7 | C33—C38—H38 | 120.6 |
C11—C12—C13 | 122.7 (4) | C37—C38—H38 | 120.6 |
C13—C12—H12 | 118.7 | C36—C39—Cd1 | 172.2 (5) |
C8—C13—C14 | 122.0 (3) | O1—C39—C36 | 120.4 (5) |
C12—C13—C8 | 118.1 (4) | O1—C39—Cd1 | 61.7 (3) |
C12—C13—C14 | 119.8 (3) | O1—C39—O2 | 122.4 (5) |
C15—C14—C13 | 110.9 (3) | O2—C39—C36 | 117.1 (6) |
C15—C14—C32 | 107.8 (3) | O2—C39—Cd1 | 61.0 (3) |
C21—C14—C13 | 108.3 (3) | O1—Cd1—C39 | 27.01 (16) |
C21—C14—C15 | 110.1 (3) | O2—Cd1—C39 | 28.21 (17) |
C21—C14—C32 | 111.3 (3) | O2—Cd1—O1 | 55.14 (16) |
C32—C14—C13 | 108.5 (3) | O3i—Cd1—C39 | 122.9 (2) |
C16—C15—C14 | 121.8 (3) | O3i—Cd1—O1 | 149.0 (2) |
C20—C15—C14 | 118.7 (4) | O3i—Cd1—O2 | 94.8 (2) |
C20—C15—C16 | 119.4 (4) | O3i—Cd1—O4ii | 100.3 (2) |
C15—C16—C17 | 119.0 (4) | O3i—Cd1—O5 | 113.4 (2) |
C15—C16—N1 | 121.1 (4) | O3i—Cd1—O6 | 90.8 (3) |
C17—C16—N1 | 119.9 (4) | O4ii—Cd1—C39 | 84.5 (2) |
C16—C17—H17 | 119.6 | O4ii—Cd1—O1 | 86.37 (19) |
C18—C17—C16 | 120.7 (5) | O4ii—Cd1—O2 | 86.7 (2) |
C18—C17—H17 | 119.6 | O5—Cd1—C39 | 123.00 (17) |
C17—C18—H18 | 120.1 | O5—Cd1—O1 | 97.59 (15) |
C17—C18—C19 | 119.8 (5) | O5—Cd1—O2 | 149.42 (13) |
C19—C18—H18 | 120.1 | O5—Cd1—O4ii | 77.1 (2) |
C18—C19—H19 | 120.3 | O5—Cd1—O6 | 90.8 (4) |
C20—C19—C18 | 119.4 (4) | O6—Cd1—C39 | 96.6 (3) |
C20—C19—H19 | 120.3 | O6—Cd1—O1 | 88.4 (2) |
C15—C20—H20 | 119.1 | O6—Cd1—O2 | 100.9 (4) |
C19—C20—C15 | 121.7 (5) | O6—Cd1—O4ii | 166.0 (4) |
C19—C20—H20 | 119.1 | C8—N1—C5 | 119.9 (4) |
C22—C21—C14 | 118.9 (3) | C8—N1—C16 | 121.0 (4) |
C22—C21—C26 | 118.5 (4) | C16—N1—C5 | 119.1 (4) |
C26—C21—C14 | 122.6 (3) | C26—N2—C27 | 121.2 (3) |
C21—C22—H22 | 119.1 | C26—N2—C33 | 119.8 (4) |
C23—C22—C21 | 121.8 (4) | C27—N2—C33 | 118.3 (3) |
C23—C22—H22 | 119.1 | C39—O1—Cd1 | 91.3 (3) |
C22—C23—H23 | 120.5 | C39—O2—Cd1 | 90.8 (4) |
C24—C23—C22 | 118.9 (4) | C1—O3—Cd1iii | 109.9 (5) |
C24—C23—H23 | 120.5 | C1—O4—Cd1ii | 164.3 (5) |
C23—C24—H24 | 119.2 | Cd1iv—O5—Cd1 | 102.9 (3) |
C23—C24—C25 | 121.6 (4) | Cd1—O5—H5A | 111.2 |
C25—C24—H24 | 119.2 | Cd1iv—O5—H5A | 111.2 |
C24—C25—H25 | 120.1 | Cd1—O5—H5B | 111.2 |
C24—C25—C26 | 119.7 (4) | Cd1iv—O5—H5B | 111.2 |
C26—C25—H25 | 120.1 | H5A—O5—H5B | 109.1 |
C21—C26—C25 | 119.3 (4) | Cd1—O6—H6A | 109.1 |
C21—C26—N2 | 120.9 (4) | Cd1—O6—H6B | 108.9 |
N2—C26—C25 | 119.8 (4) | H6A—O6—H6B | 109.4 |
C32—C27—C28 | 119.6 (4) | | |
| | | |
C1—C2—C3—C4 | −177.1 (5) | C28—C29—C30—C31 | 3.1 (8) |
C1—C2—C7—C6 | 178.2 (6) | C29—C30—C31—C32 | −2.6 (7) |
C2—C1—O3—Cd1iii | −178.7 (5) | C30—C31—C32—C14 | −178.7 (4) |
C2—C1—O4—Cd1ii | −132 (2) | C30—C31—C32—C27 | 1.6 (7) |
C2—C3—C4—C5 | 0.8 (8) | C32—C14—C15—C16 | 104.0 (4) |
C3—C2—C7—C6 | 3.0 (9) | C32—C14—C15—C20 | −72.7 (4) |
C3—C4—C5—C6 | −0.4 (8) | C32—C14—C21—C22 | 175.0 (3) |
C3—C4—C5—N1 | 177.6 (4) | C32—C14—C21—C26 | −5.6 (5) |
C4—C5—C6—C7 | 1.3 (9) | C32—C27—C28—C29 | 1.6 (8) |
C4—C5—N1—C8 | −87.5 (6) | C32—C27—N2—C26 | −5.2 (7) |
C4—C5—N1—C16 | 91.7 (6) | C32—C27—N2—C33 | 165.3 (4) |
C5—C6—C7—C2 | −2.6 (10) | C33—C34—C35—C36 | 0.0 (9) |
C6—C5—N1—C8 | 90.5 (6) | C34—C33—C38—C37 | 0.7 (10) |
C6—C5—N1—C16 | −90.3 (6) | C34—C33—N2—C26 | −98.3 (6) |
C7—C2—C3—C4 | −2.1 (8) | C34—C33—N2—C27 | 91.1 (6) |
C8—C9—C10—C11 | 0.4 (6) | C34—C35—C36—C37 | 0.3 (9) |
C8—C13—C14—C15 | 14.7 (5) | C34—C35—C36—C39 | 177.5 (6) |
C8—C13—C14—C21 | 135.6 (3) | C35—C36—C37—C38 | 0.0 (11) |
C8—C13—C14—C32 | −103.5 (4) | C35—C36—C39—Cd1 | −103 (3) |
C9—C8—C13—C12 | 0.7 (5) | C35—C36—C39—O1 | 0.6 (9) |
C9—C8—C13—C14 | 176.7 (3) | C35—C36—C39—O2 | −177.1 (6) |
C9—C8—N1—C5 | −10.4 (6) | C36—C37—C38—C33 | −0.5 (11) |
C9—C8—N1—C16 | 170.4 (4) | C36—C39—Cd1—O1 | 108 (4) |
C9—C10—C11—C12 | −0.9 (6) | C36—C39—Cd1—O2 | −78 (3) |
C10—C11—C12—C13 | 1.3 (6) | C36—C39—Cd1—O3i | −84 (3) |
C11—C12—C13—C8 | −1.2 (6) | C36—C39—Cd1—O4ii | 15 (3) |
C11—C12—C13—C14 | −177.3 (3) | C36—C39—Cd1—O5 | 86 (3) |
C12—C13—C14—C15 | −169.3 (3) | C36—C39—Cd1—O6 | −179 (100) |
C12—C13—C14—C21 | −48.5 (4) | C36—C39—O1—Cd1 | −171.4 (5) |
C12—C13—C14—C32 | 72.4 (4) | C36—C39—O2—Cd1 | 171.4 (5) |
C13—C8—C9—C10 | −0.3 (6) | C37—C36—C39—Cd1 | 74 (4) |
C13—C8—N1—C5 | 170.0 (4) | C37—C36—C39—O1 | 177.8 (6) |
C13—C8—N1—C16 | −9.2 (6) | C37—C36—C39—O2 | 0.1 (10) |
C13—C14—C15—C16 | −14.6 (5) | C38—C33—C34—C35 | −0.4 (9) |
C13—C14—C15—C20 | 168.7 (3) | C38—C33—N2—C26 | 83.7 (7) |
C13—C14—C21—C22 | −65.9 (4) | C38—C33—N2—C27 | −86.9 (6) |
C13—C14—C21—C26 | 113.6 (4) | C39—C36—C37—C38 | −177.2 (6) |
C13—C14—C32—C27 | −113.3 (4) | C39—Cd1—O5—Cd1iv | −116.36 (19) |
C13—C14—C32—C31 | 67.0 (5) | N1—C5—C6—C7 | −176.6 (5) |
C14—C15—C16—C17 | −173.9 (4) | N1—C8—C9—C10 | −179.9 (4) |
C14—C15—C16—N1 | 3.8 (6) | N1—C8—C13—C12 | −179.7 (4) |
C14—C15—C20—C19 | 174.7 (4) | N1—C8—C13—C14 | −3.7 (6) |
C14—C21—C22—C23 | 179.1 (4) | N1—C16—C17—C18 | −179.6 (5) |
C14—C21—C26—C25 | −179.7 (4) | N2—C27—C28—C29 | −178.4 (5) |
C14—C21—C26—N2 | 0.5 (6) | N2—C27—C32—C14 | −0.8 (7) |
C15—C14—C21—C22 | 55.5 (5) | N2—C27—C32—C31 | 178.9 (4) |
C15—C14—C21—C26 | −125.1 (4) | N2—C33—C34—C35 | −178.4 (5) |
C15—C14—C32—C27 | 126.6 (4) | N2—C33—C38—C37 | 178.7 (6) |
C15—C14—C32—C31 | −53.1 (5) | O1—C39—Cd1—O2 | 174.1 (7) |
C15—C16—C17—C18 | −2.0 (7) | O1—C39—Cd1—O3i | 168.5 (4) |
C15—C16—N1—C5 | −170.0 (4) | O1—C39—Cd1—O4ii | −92.8 (4) |
C15—C16—N1—C8 | 9.3 (6) | O1—C39—Cd1—O5 | −22.0 (5) |
C16—C15—C20—C19 | −2.0 (7) | O1—C39—Cd1—O6 | 73.2 (5) |
C16—C17—C18—C19 | 0.3 (8) | O1—C39—O2—Cd1 | −6.2 (7) |
C17—C16—N1—C5 | 7.6 (7) | O1—Cd1—O2—C39 | 3.3 (4) |
C17—C16—N1—C8 | −173.1 (4) | O1—Cd1—O5—Cd1iv | −126.24 (11) |
C17—C18—C19—C20 | 0.5 (8) | O2—C39—Cd1—O1 | −174.1 (7) |
C18—C19—C20—C15 | 0.4 (8) | O2—C39—Cd1—O3i | −5.6 (5) |
C20—C15—C16—C17 | 2.8 (6) | O2—C39—Cd1—O4ii | 93.2 (5) |
C20—C15—C16—N1 | −179.6 (4) | O2—C39—Cd1—O5 | 163.9 (4) |
C21—C14—C15—C16 | −134.5 (4) | O2—C39—Cd1—O6 | −100.8 (6) |
C21—C14—C15—C20 | 48.9 (5) | O2—C39—O1—Cd1 | 6.1 (7) |
C21—C14—C32—C27 | 5.7 (5) | O2—Cd1—O1—C39 | −3.4 (4) |
C21—C14—C32—C31 | −174.0 (4) | O2—Cd1—O5—Cd1iv | −101.5 (4) |
C21—C22—C23—C24 | 1.3 (7) | O3—C1—C2—C3 | 180.0 (7) |
C21—C26—N2—C27 | 5.3 (7) | O3—C1—C2—C7 | 4.8 (10) |
C21—C26—N2—C33 | −165.0 (4) | O3—C1—O4—Cd1ii | 50 (3) |
C22—C21—C26—C25 | −0.2 (6) | O3i—Cd1—O1—C39 | −19.0 (6) |
C22—C21—C26—N2 | 179.9 (4) | O3i—Cd1—O2—C39 | 175.3 (4) |
C22—C23—C24—C25 | −1.5 (7) | O3i—Cd1—O5—Cd1iv | 54.05 (19) |
C23—C24—C25—C26 | 0.9 (8) | O4—C1—C2—C3 | 2.3 (10) |
C24—C25—C26—C21 | 0.0 (7) | O4—C1—C2—C7 | −172.8 (7) |
C24—C25—C26—N2 | 179.8 (5) | O4—C1—O3—Cd1iii | −1.1 (9) |
C25—C26—N2—C27 | −174.5 (5) | O4ii—Cd1—O1—C39 | 85.1 (4) |
C25—C26—N2—C33 | 15.1 (7) | O4ii—Cd1—O2—C39 | −84.6 (5) |
C26—C21—C22—C23 | −0.4 (6) | O4ii—Cd1—O5—Cd1iv | −41.74 (16) |
C27—C28—C29—C30 | −2.7 (8) | O5—Cd1—O1—C39 | 161.5 (4) |
C28—C27—C32—C14 | 179.2 (4) | O5—Cd1—O2—C39 | −27.1 (7) |
C28—C27—C32—C31 | −1.1 (7) | O6—Cd1—O1—C39 | −107.9 (5) |
C28—C27—N2—C26 | 174.8 (5) | O6—Cd1—O2—C39 | 83.5 (5) |
C28—C27—N2—C33 | −14.6 (7) | O6—Cd1—O5—Cd1iv | 145.28 (19) |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z−1/2; (iv) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C23—H23···Cg1iv | 0.93 | 2.66 | 3.5712 (4) | 168 |
C29—H29···Cg1v | 0.93 | 2.69 | 3.5457 (4) | 154 |
Symmetry codes: (iv) −x+1, y, −z+3/2; (v) x+3/2, y+3/2, z+1. |
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