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The coordination polyhedron of the Cd2+ ion in the title compound is a CdN2O5 pentagonal bipyramid formed by two bidentately coordinated carboxylic groups of different anions, one water molecule and two pyridine molecules. In the crystal, polymeric chains propagate along the [1
1] direction; the chains are linked by hydrogen bonds and π–π stacking interactions into a three-dimensional network.
Keywords: crystal structure; coordination polymer; cadmium; 4,4′-(1H-1,2,4-triazole-3,5-diyl)dibenzoate; π-stacking; hydrogen bonds.
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989024000185/hb8090sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2056989024000185/hb8090Isup2.hkl |
CCDC reference: 2321203
Computing details top
catena-Poly[[[aquabis(pyridine-κN)cadmium(II)]-µ2-4,4'-(1H-1,2,4-triazole-3,5-diyl)dibenzoato-κ4O,O':O'',O'''] 4.5-hydrate] top
Crystal data top
[Cd(C16H9N3O4)(C5H5N)2(H2O)]·4.5H2O | Z = 2 |
Mr = 676.95 | F(000) = 690 |
Triclinic, P1 | Dx = 1.544 Mg m−3 |
a = 8.1674 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.3033 (6) Å | Cell parameters from 4044 reflections |
c = 15.4877 (8) Å | θ = 1.8–26.4° |
α = 75.226 (5)° | µ = 0.81 mm−1 |
β = 86.412 (4)° | T = 293 K |
γ = 75.346 (5)° | Prism, clear light colourless |
V = 1455.89 (14) Å3 | 0.45 × 0.03 × 0.03 mm |
Data collection top
Rigaku Xcalibur Eos diffractometer | 5963 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 4538 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
Detector resolution: 16.1593 pixels mm-1 | θmax = 26.4°, θmin = 1.9° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022) | k = −15→15 |
Tmin = 0.850, Tmax = 1.000 | l = −19→19 |
14750 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.052 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0366P)2 + 0.076P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5963 reflections | Δρmax = 0.80 e Å−3 |
378 parameters | Δρmin = −0.70 e Å−3 |
6 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Cd1 | 0.64074 (4) | 0.33051 (3) | 0.91578 (2) | 0.03626 (11) | |
O1W | 0.4111 (5) | 0.3603 (4) | 1.0083 (2) | 0.1047 (16) | |
H1WA | 0.313054 | 0.349393 | 1.014089 | 0.157* | |
H1WB | 0.419894 | 0.382793 | 1.055479 | 0.157* | |
O2 | 0.4683 (4) | 0.4504 (2) | 0.77939 (17) | 0.0454 (7) | |
O2W | 0.5031 (4) | 0.3838 (2) | 0.62018 (18) | 0.0518 (8) | |
H2WA | 0.520004 | 0.310406 | 0.633938 | 0.078* | |
H2WB | 0.483954 | 0.402446 | 0.669698 | 0.078* | |
O1 | 0.5848 (4) | 0.5341 (2) | 0.85969 (17) | 0.0465 (8) | |
O4A | −0.1584 (8) | 1.1735 (5) | 0.0270 (4) | 0.0499 (11)* | 0.5 |
O4B | −0.2360 (7) | 1.2083 (5) | 0.0386 (4) | 0.0499 (11)* | 0.5 |
O3W | 0.2593 (4) | 0.5195 (3) | 0.49121 (19) | 0.0542 (8) | |
H3WA | 0.326207 | 0.479856 | 0.534058 | 0.081* | |
H3WB | 0.320787 | 0.553956 | 0.453168 | 0.081* | |
O3B | −0.1896 (12) | 1.3767 (5) | 0.0317 (5) | 0.0563 (12)* | 0.5 |
O3A | −0.1638 (12) | 1.3622 (4) | 0.0171 (5) | 0.0563 (12)* | 0.5 |
O4W | 0.4914 (4) | 0.8427 (3) | 0.3594 (2) | 0.0652 (9) | |
H4WA | 0.574823 | 0.858316 | 0.379584 | 0.098* | |
H4WB | 0.405463 | 0.877186 | 0.384414 | 0.098* | |
O5W | 0.0700 (4) | 1.3812 (2) | 0.44619 (18) | 0.0569 (9) | |
H5WA | −0.007980 | 1.408909 | 0.472957 | 0.085* | |
H5WB | 0.141350 | 1.418159 | 0.452907 | 0.085* | |
O6WB | 0.107 (2) | 0.4481 (17) | 0.9711 (12) | 0.060 (6)* | 0.25 |
H6WA | 0.113338 | 0.516203 | 0.970506 | 0.091* | 0.25 |
H6WB | 0.010258 | 0.439113 | 0.989916 | 0.091* | 0.25 |
O6WA | 0.139 (2) | 0.4433 (15) | 0.9539 (11) | 0.043 (5)* | 0.25 |
H6WC | 0.095554 | 0.514506 | 0.953184 | 0.064* | 0.25 |
H6WD | 0.069634 | 0.408256 | 0.985854 | 0.064* | 0.25 |
N1 | 0.5552 (5) | 0.1728 (3) | 0.8928 (2) | 0.0443 (9) | |
N2 | 0.8545 (4) | 0.3186 (3) | 0.8082 (2) | 0.0412 (8) | |
N3 | 0.1923 (5) | 1.1490 (3) | 0.4659 (2) | 0.0424 (9) | |
H3 | 0.157 (6) | 1.221 (4) | 0.458 (3) | 0.074 (18)* | |
N4 | 0.2590 (4) | 1.0777 (3) | 0.5443 (2) | 0.0417 (9) | |
N5 | 0.2250 (4) | 0.9751 (3) | 0.4486 (2) | 0.0379 (8) | |
C1 | 0.3958 (7) | 0.1841 (4) | 0.8749 (3) | 0.0740 (17) | |
H1 | 0.322541 | 0.257394 | 0.866349 | 0.089* | |
C2 | 0.3310 (9) | 0.0941 (6) | 0.8679 (4) | 0.093 (2) | |
H2 | 0.216205 | 0.105768 | 0.857408 | 0.111* | |
C3 | 0.4382 (9) | −0.0124 (5) | 0.8767 (3) | 0.0694 (17) | |
H3A | 0.398336 | −0.074680 | 0.870963 | 0.083* | |
C4 | 0.6026 (8) | −0.0266 (4) | 0.8939 (3) | 0.0706 (16) | |
H4 | 0.678469 | −0.098651 | 0.899798 | 0.085* | |
C5 | 0.6579 (7) | 0.0691 (4) | 0.9029 (3) | 0.0602 (14) | |
H5 | 0.771008 | 0.058824 | 0.916337 | 0.072* | |
C6 | 0.8673 (6) | 0.2579 (4) | 0.7471 (3) | 0.0479 (11) | |
H6 | 0.792523 | 0.211298 | 0.750025 | 0.057* | |
C7 | 0.9838 (7) | 0.2607 (4) | 0.6807 (3) | 0.0602 (14) | |
H7 | 0.987319 | 0.217255 | 0.639187 | 0.072* | |
C8 | 1.0954 (6) | 0.3276 (4) | 0.6753 (3) | 0.0627 (14) | |
H8 | 1.177391 | 0.329792 | 0.630844 | 0.075* | |
C9 | 1.0841 (6) | 0.3916 (4) | 0.7371 (3) | 0.0605 (13) | |
H9 | 1.157265 | 0.439178 | 0.734878 | 0.073* | |
C10 | 0.9630 (6) | 0.3840 (4) | 0.8021 (3) | 0.0532 (12) | |
H10 | 0.956621 | 0.427068 | 0.844150 | 0.064* | |
C11 | 0.5034 (5) | 0.5385 (4) | 0.7923 (2) | 0.0368 (10) | |
C12 | 0.4477 (5) | 0.6532 (3) | 0.7247 (2) | 0.0336 (9) | |
C13 | 0.3618 (6) | 0.6598 (4) | 0.6490 (3) | 0.0480 (12) | |
H13 | 0.338297 | 0.593176 | 0.640321 | 0.058* | |
C14 | 0.3102 (6) | 0.7635 (4) | 0.5858 (3) | 0.0471 (11) | |
H14 | 0.254292 | 0.765596 | 0.534647 | 0.057* | |
C15 | 0.3407 (5) | 0.8642 (3) | 0.5976 (2) | 0.0368 (10) | |
C16 | 0.4270 (6) | 0.8581 (4) | 0.6736 (3) | 0.0445 (11) | |
H16 | 0.449859 | 0.924632 | 0.682696 | 0.053* | |
C17 | 0.4793 (5) | 0.7534 (4) | 0.7362 (3) | 0.0417 (10) | |
H17 | 0.536932 | 0.750681 | 0.786919 | 0.050* | |
C18 | 0.2774 (5) | 0.9730 (3) | 0.5311 (2) | 0.0360 (10) | |
C19 | 0.1713 (5) | 1.0868 (3) | 0.4092 (2) | 0.0346 (9) | |
C20 | 0.0987 (5) | 1.1348 (3) | 0.3197 (2) | 0.0344 (9) | |
C21 | 0.0451 (6) | 1.0618 (4) | 0.2790 (3) | 0.0478 (11) | |
H21 | 0.060249 | 0.983834 | 0.308029 | 0.057* | |
C22 | −0.0295 (6) | 1.1028 (4) | 0.1969 (3) | 0.0541 (13) | |
H22 | −0.064227 | 1.052054 | 0.170832 | 0.065* | |
C23 | −0.0546 (5) | 1.2180 (4) | 0.1514 (3) | 0.0436 (11) | |
C24 | 0.0025 (6) | 1.2910 (4) | 0.1910 (3) | 0.0508 (12) | |
H24 | −0.010726 | 1.368636 | 0.161499 | 0.061* | |
C25 | 0.0788 (6) | 1.2489 (4) | 0.2741 (3) | 0.0519 (12) | |
H25 | 0.117281 | 1.298581 | 0.299591 | 0.062* | |
C26 | −0.1447 (6) | 1.2612 (3) | 0.0646 (3) | 0.0610 (14) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.0489 (2) | 0.03543 (19) | 0.02777 (17) | −0.01675 (15) | −0.00309 (13) | −0.00652 (12) |
O1W | 0.113 (3) | 0.178 (4) | 0.091 (3) | −0.104 (3) | 0.064 (2) | −0.102 (3) |
O2 | 0.062 (2) | 0.0361 (17) | 0.0383 (16) | −0.0176 (15) | −0.0097 (14) | −0.0012 (13) |
O2W | 0.063 (2) | 0.0454 (19) | 0.0480 (18) | −0.0131 (16) | −0.0013 (16) | −0.0126 (15) |
O1 | 0.065 (2) | 0.0382 (17) | 0.0318 (15) | −0.0016 (15) | −0.0174 (15) | −0.0081 (13) |
O3W | 0.046 (2) | 0.061 (2) | 0.0555 (19) | −0.0169 (16) | −0.0044 (15) | −0.0104 (16) |
O4W | 0.075 (2) | 0.048 (2) | 0.075 (2) | −0.0079 (18) | 0.0133 (19) | −0.0310 (18) |
O5W | 0.072 (2) | 0.0369 (19) | 0.063 (2) | −0.0028 (16) | −0.0130 (17) | −0.0209 (16) |
N1 | 0.064 (3) | 0.037 (2) | 0.0347 (19) | −0.023 (2) | −0.0113 (18) | −0.0010 (16) |
N2 | 0.046 (2) | 0.039 (2) | 0.039 (2) | −0.0142 (18) | 0.0006 (17) | −0.0057 (17) |
N3 | 0.060 (3) | 0.025 (2) | 0.034 (2) | 0.0077 (19) | −0.0170 (17) | −0.0070 (16) |
N4 | 0.055 (2) | 0.033 (2) | 0.0308 (18) | 0.0037 (18) | −0.0132 (16) | −0.0083 (15) |
N5 | 0.045 (2) | 0.032 (2) | 0.0330 (19) | 0.0008 (16) | −0.0100 (16) | −0.0099 (16) |
C1 | 0.080 (4) | 0.045 (3) | 0.093 (4) | −0.021 (3) | −0.051 (3) | 0.006 (3) |
C2 | 0.102 (5) | 0.077 (5) | 0.107 (5) | −0.045 (4) | −0.057 (4) | −0.001 (4) |
C3 | 0.113 (5) | 0.063 (4) | 0.050 (3) | −0.051 (4) | 0.000 (3) | −0.016 (3) |
C4 | 0.098 (5) | 0.046 (3) | 0.076 (4) | −0.029 (3) | 0.033 (3) | −0.024 (3) |
C5 | 0.068 (4) | 0.052 (3) | 0.069 (3) | −0.028 (3) | 0.021 (3) | −0.022 (3) |
C6 | 0.060 (3) | 0.048 (3) | 0.041 (3) | −0.023 (2) | 0.007 (2) | −0.011 (2) |
C7 | 0.074 (4) | 0.058 (3) | 0.049 (3) | −0.019 (3) | 0.014 (3) | −0.015 (2) |
C8 | 0.056 (3) | 0.065 (4) | 0.050 (3) | −0.007 (3) | 0.010 (3) | 0.006 (3) |
C9 | 0.044 (3) | 0.067 (4) | 0.067 (3) | −0.027 (3) | −0.002 (3) | 0.003 (3) |
C10 | 0.055 (3) | 0.056 (3) | 0.053 (3) | −0.023 (3) | −0.004 (2) | −0.011 (2) |
C11 | 0.036 (2) | 0.041 (3) | 0.030 (2) | −0.003 (2) | 0.0027 (18) | −0.0099 (19) |
C12 | 0.032 (2) | 0.036 (2) | 0.031 (2) | −0.0028 (19) | −0.0030 (17) | −0.0096 (18) |
C13 | 0.067 (3) | 0.037 (3) | 0.042 (3) | −0.010 (2) | −0.018 (2) | −0.013 (2) |
C14 | 0.061 (3) | 0.041 (3) | 0.038 (2) | −0.008 (2) | −0.025 (2) | −0.005 (2) |
C15 | 0.041 (3) | 0.031 (2) | 0.033 (2) | 0.0023 (19) | −0.0064 (18) | −0.0067 (18) |
C16 | 0.058 (3) | 0.035 (3) | 0.042 (2) | −0.006 (2) | −0.013 (2) | −0.013 (2) |
C17 | 0.050 (3) | 0.039 (3) | 0.035 (2) | −0.005 (2) | −0.014 (2) | −0.011 (2) |
C18 | 0.039 (2) | 0.033 (2) | 0.031 (2) | 0.0001 (19) | −0.0046 (18) | −0.0079 (18) |
C19 | 0.037 (2) | 0.035 (2) | 0.030 (2) | −0.0023 (19) | −0.0053 (18) | −0.0101 (18) |
C20 | 0.037 (2) | 0.038 (3) | 0.026 (2) | −0.0028 (19) | −0.0077 (17) | −0.0077 (18) |
C21 | 0.058 (3) | 0.048 (3) | 0.043 (3) | −0.020 (2) | −0.009 (2) | −0.010 (2) |
C22 | 0.069 (3) | 0.066 (3) | 0.037 (3) | −0.037 (3) | −0.017 (2) | −0.009 (2) |
C23 | 0.043 (3) | 0.062 (3) | 0.029 (2) | −0.024 (2) | −0.0029 (19) | −0.005 (2) |
C24 | 0.067 (3) | 0.043 (3) | 0.036 (2) | −0.008 (2) | −0.019 (2) | 0.003 (2) |
C25 | 0.075 (4) | 0.042 (3) | 0.039 (3) | −0.011 (3) | −0.023 (2) | −0.008 (2) |
C26 | 0.056 (3) | 0.099 (4) | 0.042 (3) | −0.051 (3) | −0.002 (2) | −0.011 (3) |
Geometric parameters (Å, º) top
Cd1—O1W | 2.300 (3) | C2—H2 | 0.9300 |
Cd1—O2 | 2.521 (3) | C2—C3 | 1.359 (8) |
Cd1—O1 | 2.366 (3) | C3—H3A | 0.9300 |
Cd1—O4Ai | 2.538 (6) | C3—C4 | 1.345 (7) |
Cd1—O4Bi | 2.216 (6) | C4—H4 | 0.9300 |
Cd1—O3Bi | 2.588 (10) | C4—C5 | 1.403 (6) |
Cd1—O3Ai | 2.471 (10) | C5—H5 | 0.9300 |
Cd1—N1 | 2.334 (3) | C6—H6 | 0.9300 |
Cd1—N2 | 2.340 (3) | C6—C7 | 1.356 (6) |
O1W—H1WA | 0.8401 | C7—H7 | 0.9300 |
O1W—H1WB | 0.8579 | C7—C8 | 1.360 (6) |
O2—C11 | 1.254 (4) | C8—H8 | 0.9300 |
O2W—H2WA | 0.8498 | C8—C9 | 1.372 (6) |
O2W—H2WB | 0.8496 | C9—H9 | 0.9300 |
O1—C11 | 1.255 (4) | C9—C10 | 1.369 (6) |
O4A—C26 | 1.379 (5) | C10—H10 | 0.9300 |
O4B—C26 | 1.2476 (10) | C11—C12 | 1.509 (5) |
O3W—H3WA | 0.8498 | C12—C13 | 1.378 (5) |
O3W—H3WB | 0.8500 | C12—C17 | 1.377 (5) |
O3B—C26 | 1.343 (6) | C13—H13 | 0.9300 |
O3A—C26 | 1.2485 (10) | C13—C14 | 1.381 (5) |
O4W—H4WA | 0.8500 | C14—H14 | 0.9300 |
O4W—H4WB | 0.8501 | C14—C15 | 1.381 (5) |
O5W—H5WA | 0.7895 | C15—C16 | 1.386 (5) |
O5W—H5WB | 0.8503 | C15—C18 | 1.461 (5) |
O6WB—H6WA | 0.8499 | C16—H16 | 0.9300 |
O6WB—H6WB | 0.8497 | C16—C17 | 1.384 (5) |
O6WA—H6WC | 0.8547 | C17—H17 | 0.9300 |
O6WA—H6WD | 0.8535 | C19—C20 | 1.459 (5) |
N1—C1 | 1.314 (6) | C20—C21 | 1.385 (5) |
N1—C5 | 1.315 (6) | C20—C25 | 1.374 (5) |
N2—C6 | 1.332 (5) | C21—H21 | 0.9300 |
N2—C10 | 1.324 (5) | C21—C22 | 1.363 (5) |
N3—H3 | 0.83 (5) | C22—H22 | 0.9300 |
N3—N4 | 1.355 (4) | C22—C23 | 1.382 (6) |
N3—C19 | 1.347 (5) | C23—C24 | 1.389 (5) |
N4—C18 | 1.325 (5) | C23—C26 | 1.481 (5) |
N5—C18 | 1.364 (4) | C24—H24 | 0.9300 |
N5—C19 | 1.324 (5) | C24—C25 | 1.382 (5) |
C1—H1 | 0.9300 | C25—H25 | 0.9300 |
C1—C2 | 1.372 (6) | ||
O1W—Cd1—O2 | 92.10 (13) | C5—C4—H4 | 120.6 |
O1W—Cd1—O1 | 87.97 (13) | N1—C5—C4 | 122.3 (5) |
O1W—Cd1—O4Ai | 98.35 (18) | N1—C5—H5 | 118.9 |
O1W—Cd1—O3Bi | 86.8 (2) | C4—C5—H5 | 118.9 |
O1W—Cd1—O3Ai | 93.9 (2) | N2—C6—H6 | 118.3 |
O1W—Cd1—N1 | 88.03 (12) | N2—C6—C7 | 123.4 (4) |
O1W—Cd1—N2 | 172.97 (14) | C7—C6—H6 | 118.3 |
O2—Cd1—O4Ai | 164.94 (13) | C6—C7—H7 | 120.3 |
O2—Cd1—O3Bi | 134.39 (13) | C6—C7—C8 | 119.5 (4) |
O1—Cd1—O2 | 53.22 (8) | C8—C7—H7 | 120.3 |
O1—Cd1—O4Ai | 137.54 (13) | C7—C8—H8 | 120.8 |
O1—Cd1—O3Bi | 81.19 (13) | C7—C8—C9 | 118.3 (4) |
O1—Cd1—O3Ai | 83.77 (11) | C9—C8—H8 | 120.8 |
O4Bi—Cd1—O1W | 83.36 (19) | C8—C9—H9 | 120.7 |
O4Bi—Cd1—O2 | 171.16 (12) | C10—C9—C8 | 118.7 (4) |
O4Bi—Cd1—O1 | 133.80 (12) | C10—C9—H9 | 120.7 |
O4Bi—Cd1—O4Ai | 15.3 (2) | N2—C10—C9 | 123.4 (4) |
O4Bi—Cd1—O3Bi | 53.15 (14) | N2—C10—H10 | 118.3 |
O4Bi—Cd1—O3Ai | 51.93 (13) | C9—C10—H10 | 118.3 |
O4Bi—Cd1—N1 | 85.58 (13) | O2—C11—O1 | 121.9 (4) |
O4Bi—Cd1—N2 | 103.63 (18) | O2—C11—C12 | 119.3 (3) |
O3Ai—Cd1—O2 | 136.29 (11) | O1—C11—C12 | 118.8 (3) |
N1—Cd1—O2 | 86.69 (10) | C13—C12—C11 | 119.9 (3) |
N1—Cd1—O1 | 139.50 (11) | C17—C12—C11 | 121.9 (3) |
N1—Cd1—O4Ai | 82.87 (14) | C17—C12—C13 | 118.2 (4) |
N1—Cd1—O3Bi | 138.73 (14) | C12—C13—H13 | 119.4 |
N1—Cd1—O3Ai | 136.72 (13) | C12—C13—C14 | 121.1 (4) |
N1—Cd1—N2 | 93.18 (12) | C14—C13—H13 | 119.4 |
N2—Cd1—O2 | 81.06 (10) | C13—C14—H14 | 119.6 |
N2—Cd1—O1 | 86.61 (11) | C13—C14—C15 | 120.7 (4) |
N2—Cd1—O4Ai | 88.68 (16) | C15—C14—H14 | 119.6 |
N2—Cd1—O3Bi | 96.7 (2) | C14—C15—C16 | 118.4 (4) |
N2—Cd1—O3Ai | 89.9 (2) | C14—C15—C18 | 119.0 (3) |
Cd1—O1W—H1WA | 138.5 | C16—C15—C18 | 122.7 (4) |
Cd1—O1W—H1WB | 119.7 | C15—C16—H16 | 119.8 |
H1WA—O1W—H1WB | 101.4 | C17—C16—C15 | 120.4 (4) |
C11—O2—Cd1 | 88.7 (2) | C17—C16—H16 | 119.8 |
H2WA—O2W—H2WB | 104.5 | C12—C17—C16 | 121.2 (4) |
C11—O1—Cd1 | 95.9 (2) | C12—C17—H17 | 119.4 |
C26—O4A—Cd1ii | 86.0 (3) | C16—C17—H17 | 119.4 |
C26—O4B—Cd1ii | 104.5 (4) | N4—C18—N5 | 113.3 (3) |
H3WA—O3W—H3WB | 104.5 | N4—C18—C15 | 124.8 (3) |
C26—O3B—Cd1ii | 84.7 (4) | N5—C18—C15 | 121.8 (3) |
C26—O3A—Cd1ii | 91.8 (5) | N3—C19—C20 | 125.6 (4) |
H4WA—O4W—H4WB | 104.5 | N5—C19—N3 | 108.8 (3) |
H5WA—O5W—H5WB | 101.0 | N5—C19—C20 | 125.7 (3) |
H6WA—O6WB—H6WB | 109.5 | C21—C20—C19 | 118.3 (4) |
H6WC—O6WA—H6WD | 103.5 | C25—C20—C19 | 123.5 (3) |
C1—N1—Cd1 | 119.7 (3) | C25—C20—C21 | 118.2 (4) |
C1—N1—C5 | 117.4 (4) | C20—C21—H21 | 119.6 |
C5—N1—Cd1 | 122.8 (3) | C22—C21—C20 | 120.9 (4) |
C6—N2—Cd1 | 124.7 (3) | C22—C21—H21 | 119.6 |
C10—N2—Cd1 | 118.3 (3) | C21—C22—H22 | 119.3 |
C10—N2—C6 | 116.8 (4) | C21—C22—C23 | 121.5 (4) |
N4—N3—H3 | 123 (3) | C23—C22—H22 | 119.3 |
C19—N3—H3 | 126 (3) | C22—C23—C24 | 117.9 (4) |
C19—N3—N4 | 110.5 (3) | C22—C23—C26 | 120.1 (3) |
C18—N4—N3 | 103.0 (3) | C24—C23—C26 | 122.0 (4) |
C19—N5—C18 | 104.4 (3) | C23—C24—H24 | 119.8 |
N1—C1—H1 | 118.1 | C25—C24—C23 | 120.4 (4) |
N1—C1—C2 | 123.9 (5) | C25—C24—H24 | 119.8 |
C2—C1—H1 | 118.1 | C20—C25—C24 | 121.1 (4) |
C1—C2—H2 | 120.7 | C20—C25—H25 | 119.4 |
C3—C2—C1 | 118.5 (6) | C24—C25—H25 | 119.4 |
C3—C2—H2 | 120.7 | O4A—C26—C23 | 113.2 (4) |
C2—C3—H3A | 120.5 | O4B—C26—O3B | 114.1 (6) |
C4—C3—C2 | 119.1 (5) | O4B—C26—C23 | 123.3 (4) |
C4—C3—H3A | 120.5 | O3B—C26—C23 | 116.7 (5) |
C3—C4—H4 | 120.6 | O3A—C26—O4A | 119.9 (6) |
C3—C4—C5 | 118.8 (5) | O3A—C26—C23 | 123.9 (5) |
Cd1—O2—C11—O1 | −4.7 (4) | C10—N2—C6—C7 | −0.1 (7) |
Cd1—O2—C11—C12 | 174.7 (3) | C11—C12—C13—C14 | −179.6 (4) |
Cd1—O1—C11—O2 | 5.1 (4) | C11—C12—C17—C16 | −179.8 (4) |
Cd1—O1—C11—C12 | −174.4 (3) | C12—C13—C14—C15 | −1.2 (7) |
Cd1ii—O4A—C26—O3A | −28.7 (7) | C13—C12—C17—C16 | −0.1 (6) |
Cd1ii—O4A—C26—C23 | 170.0 (3) | C13—C14—C15—C16 | 1.2 (7) |
Cd1ii—O4B—C26—O3B | 20.2 (7) | C13—C14—C15—C18 | −177.3 (4) |
Cd1ii—O4B—C26—C23 | 172.0 (4) | C14—C15—C16—C17 | −0.7 (6) |
Cd1ii—O3B—C26—O4B | −16.7 (6) | C14—C15—C18—N4 | 162.0 (4) |
Cd1ii—O3B—C26—C23 | −170.4 (4) | C14—C15—C18—N5 | −15.6 (6) |
Cd1ii—O3A—C26—O4A | 29.5 (7) | C15—C16—C17—C12 | 0.1 (7) |
Cd1ii—O3A—C26—C23 | −171.3 (4) | C16—C15—C18—N4 | −16.5 (6) |
Cd1—N1—C1—C2 | −174.2 (4) | C16—C15—C18—N5 | 166.0 (4) |
Cd1—N1—C5—C4 | 176.2 (3) | C17—C12—C13—C14 | 0.6 (7) |
Cd1—N2—C6—C7 | 174.0 (4) | C18—N5—C19—N3 | 0.6 (4) |
Cd1—N2—C10—C9 | −174.4 (4) | C18—N5—C19—C20 | −178.6 (4) |
O2—C11—C12—C13 | −1.2 (6) | C18—C15—C16—C17 | 177.8 (4) |
O2—C11—C12—C17 | 178.6 (4) | C19—N3—N4—C18 | 0.6 (4) |
O1—C11—C12—C13 | 178.3 (4) | C19—N5—C18—N4 | −0.2 (5) |
O1—C11—C12—C17 | −1.9 (6) | C19—N5—C18—C15 | 177.6 (4) |
N1—C1—C2—C3 | −2.6 (9) | C19—C20—C21—C22 | 177.5 (4) |
N2—C6—C7—C8 | 0.5 (8) | C19—C20—C25—C24 | −177.1 (4) |
N3—N4—C18—N5 | −0.2 (5) | C20—C21—C22—C23 | −0.1 (7) |
N3—N4—C18—C15 | −178.0 (4) | C21—C20—C25—C24 | 2.0 (7) |
N3—C19—C20—C21 | −163.4 (4) | C21—C22—C23—C24 | 1.6 (7) |
N3—C19—C20—C25 | 15.7 (7) | C21—C22—C23—C26 | −176.5 (4) |
N4—N3—C19—N5 | −0.7 (5) | C22—C23—C24—C25 | −1.2 (7) |
N4—N3—C19—C20 | 178.4 (4) | C22—C23—C26—O4A | −15.3 (7) |
N5—C19—C20—C21 | 15.5 (6) | C22—C23—C26—O4B | 18.0 (8) |
N5—C19—C20—C25 | −165.3 (4) | C22—C23—C26—O3B | 169.1 (6) |
C1—N1—C5—C4 | 0.8 (7) | C22—C23—C26—O3A | −175.7 (7) |
C1—C2—C3—C4 | 1.5 (9) | C23—C24—C25—C20 | −0.6 (7) |
C2—C3—C4—C5 | 0.5 (8) | C24—C23—C26—O4A | 166.7 (5) |
C3—C4—C5—N1 | −1.7 (7) | C24—C23—C26—O4B | −160.1 (5) |
C5—N1—C1—C2 | 1.4 (8) | C24—C23—C26—O3B | −8.9 (8) |
C6—N2—C10—C9 | 0.1 (7) | C24—C23—C26—O3A | 6.2 (9) |
C6—C7—C8—C9 | −1.0 (8) | C25—C20—C21—C22 | −1.7 (7) |
C7—C8—C9—C10 | 1.0 (7) | C26—C23—C24—C25 | 176.8 (4) |
C8—C9—C10—N2 | −0.6 (7) |
Symmetry codes: (i) x+1, y−1, z+1; (ii) x−1, y+1, z−1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WB···O1iii | 0.86 | 1.85 | 2.694 (4) | 166 |
O2W—H2WA···O4Wiv | 0.85 | 1.89 | 2.712 (4) | 164 |
O2W—H2WB···O2 | 0.85 | 1.92 | 2.767 (4) | 173 |
O3W—H3WA···O2W | 0.85 | 1.96 | 2.803 (4) | 172 |
O3W—H3WB···O2Wiv | 0.85 | 1.96 | 2.804 (4) | 170 |
O4W—H4WA···N4v | 0.85 | 2.25 | 3.079 (4) | 165 |
O4W—H4WB···N5 | 0.85 | 2.03 | 2.877 (4) | 171 |
O5W—H5WA···O3Wvi | 0.79 | 2.12 | 2.878 (4) | 161 |
O5W—H5WB···O3Wvii | 0.85 | 1.97 | 2.800 (4) | 164 |
N3—H3···O5W | 0.83 (5) | 1.89 (5) | 2.720 (4) | 177 (5) |
Symmetry codes: (iii) −x+1, −y+1, −z+2; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y+2, −z+1; (vi) −x, −y+2, −z+1; (vii) x, y+1, z. |