The asymmetric unit of the title compound, (C
4H
12N
2)
3[In(C
7H
3NO
4)
3]
2·12H
2O, contains one and a half cations, one anion and six water molecules. The In
III atom is eight-coordinated by two tridentate and one bidentate pyridine-2,6-dicarboxylate ligand. Intra- and intermolecular N—H
O and O—H
O hydrogen bonds seem to be effective in the stabilization of the crystal structure, resulting in the formation of a supramolecular structure.
Supporting information
CCDC reference: 609295
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.081
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for N1 - C1 .. 10.93 su
PLAT415_ALERT_2_B Short Inter D-H..H-X H9A .. H17B .. 2.04 Ang.
Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.40
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Tris(piperazinediium)
bis[tris(pyridine-2,6-dicarboxylato)-
κ6O,
N,
O';
κ2O,
N-indiate(III)] dodecahydrate
top
Crystal data top
(C4H12N2)3[In(C7H3NO4)3]2·12H2O | F(000) = 1744 |
Mr = 1700.92 | Dx = 1.682 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8588 reflections |
a = 10.5327 (6) Å | θ = 2.2–28.0° |
b = 18.1833 (10) Å | µ = 0.79 mm−1 |
c = 17.5903 (10) Å | T = 294 K |
β = 94.687 (5)° | Prism, colorless |
V = 3357.6 (3) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 2 | |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 8030 independent reflections |
Radiation source: normal-focus sealed tube | 6914 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 28.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1998) | h = −13→13 |
Tmin = 0.797, Tmax = 0.858 | k = −24→24 |
33553 measured reflections | l = −23→23 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: mixed |
wR(F2) = 0.081 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.04P)2 + 3.2P] where P = (Fo2 + 2Fc2)/3 |
8030 reflections | (Δ/σ)max = 0.002 |
469 parameters | Δρmax = 1.25 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
In1 | 0.418200 (12) | 0.280149 (8) | 0.398697 (8) | 0.02520 (5) | |
O1 | 0.08199 (16) | 0.15210 (10) | 0.26328 (11) | 0.0433 (4) | |
O2 | 0.19583 (16) | 0.24516 (9) | 0.31658 (10) | 0.0374 (4) | |
O3 | 0.64169 (16) | 0.10304 (10) | 0.49978 (10) | 0.0433 (4) | |
O4 | 0.55392 (14) | 0.21237 (8) | 0.47459 (8) | 0.0297 (3) | |
O5 | 0.14742 (17) | 0.44459 (10) | 0.30839 (10) | 0.0419 (4) | |
O6 | 0.27632 (15) | 0.37843 (9) | 0.38847 (8) | 0.0317 (3) | |
O7 | 0.66091 (17) | 0.22943 (11) | 0.20841 (10) | 0.0467 (5) | |
O8 | 0.57649 (15) | 0.22584 (9) | 0.32056 (9) | 0.0336 (3) | |
O9 | 0.1837 (2) | 0.28054 (11) | 0.58969 (13) | 0.0557 (5) | |
O10 | 0.27318 (15) | 0.24967 (10) | 0.48326 (9) | 0.0354 (3) | |
O11 | 0.74296 (17) | 0.42876 (12) | 0.46852 (12) | 0.0523 (5) | |
O12 | 0.59912 (15) | 0.36388 (10) | 0.39651 (9) | 0.0384 (4) | |
N1 | 0.37560 (16) | 0.15416 (10) | 0.37737 (10) | 0.0276 (3) | |
N2 | 0.40464 (15) | 0.32642 (9) | 0.27798 (9) | 0.0233 (3) | |
N3 | 0.45395 (16) | 0.34884 (10) | 0.50906 (10) | 0.0293 (4) | |
C1 | 0.28003 (19) | 0.12557 (12) | 0.33035 (12) | 0.0281 (4) | |
C2 | 0.2752 (2) | 0.05096 (13) | 0.31193 (14) | 0.0358 (5) | |
H2A | 0.2098 | 0.0325 | 0.2786 | 0.043* | |
C3 | 0.3692 (2) | 0.00482 (14) | 0.34400 (16) | 0.0424 (5) | |
H3A | 0.3695 | −0.0448 | 0.3313 | 0.051* | |
C4 | 0.4626 (2) | 0.03363 (13) | 0.39513 (14) | 0.0390 (5) | |
H4A | 0.5244 | 0.0032 | 0.4193 | 0.047* | |
C5 | 0.4631 (2) | 0.10830 (12) | 0.40984 (12) | 0.0287 (4) | |
C6 | 0.1781 (2) | 0.17916 (12) | 0.30080 (12) | 0.0300 (4) | |
C7 | 0.56147 (19) | 0.14361 (12) | 0.46519 (12) | 0.0286 (4) | |
C8 | 0.31369 (18) | 0.37595 (11) | 0.25859 (11) | 0.0259 (4) | |
C9 | 0.2911 (2) | 0.40029 (12) | 0.18405 (12) | 0.0318 (4) | |
H9A | 0.2279 | 0.4349 | 0.1714 | 0.038* | |
C10 | 0.3639 (2) | 0.37234 (13) | 0.12880 (12) | 0.0330 (4) | |
H10A | 0.3481 | 0.3866 | 0.0781 | 0.040* | |
C11 | 0.4602 (2) | 0.32321 (13) | 0.14962 (12) | 0.0316 (4) | |
H11A | 0.5123 | 0.3053 | 0.1136 | 0.038* | |
C12 | 0.47798 (18) | 0.30103 (12) | 0.22490 (11) | 0.0260 (4) | |
C13 | 0.23930 (19) | 0.40186 (11) | 0.32368 (12) | 0.0274 (4) | |
C14 | 0.58099 (19) | 0.24768 (13) | 0.25317 (12) | 0.0297 (4) | |
C15 | 0.3703 (2) | 0.34247 (13) | 0.56187 (13) | 0.0351 (5) | |
C16 | 0.3810 (3) | 0.38502 (18) | 0.62747 (16) | 0.0544 (7) | |
H16C | 0.3212 | 0.3809 | 0.6633 | 0.065* | |
C17 | 0.4812 (4) | 0.4334 (2) | 0.63882 (18) | 0.0661 (9) | |
H17C | 0.4896 | 0.4624 | 0.6825 | 0.079* | |
C18 | 0.5694 (3) | 0.43867 (18) | 0.58491 (17) | 0.0528 (7) | |
H18C | 0.6386 | 0.4704 | 0.5919 | 0.063* | |
C19 | 0.5515 (2) | 0.39515 (13) | 0.52010 (13) | 0.0337 (5) | |
C20 | 0.2663 (2) | 0.28687 (13) | 0.54420 (14) | 0.0362 (5) | |
C21 | 0.6392 (2) | 0.39636 (13) | 0.45613 (14) | 0.0344 (5) | |
N4 | 0.91979 (18) | 0.24966 (11) | 0.19172 (11) | 0.0339 (4) | |
H4B | 0.8456 | 0.2577 | 0.2124 | 0.041* | |
H4C | 0.9711 | 0.2243 | 0.2257 | 0.041* | |
N5 | 0.8674 (2) | 0.32306 (13) | 0.04768 (12) | 0.0466 (5) | |
H5A | 0.9401 | 0.3196 | 0.0243 | 0.056* | |
H5B | 0.8106 | 0.3481 | 0.0167 | 0.056* | |
C22 | 0.8960 (2) | 0.20589 (14) | 0.12057 (15) | 0.0382 (5) | |
H22A | 0.8523 | 0.1607 | 0.1319 | 0.046* | |
H22B | 0.9768 | 0.1928 | 0.1015 | 0.046* | |
C23 | 0.8171 (2) | 0.24758 (15) | 0.06010 (14) | 0.0403 (5) | |
H23A | 0.8149 | 0.2204 | 0.0126 | 0.048* | |
H23B | 0.7305 | 0.2513 | 0.0747 | 0.048* | |
C24 | 0.8924 (3) | 0.36402 (14) | 0.11953 (15) | 0.0439 (6) | |
H24A | 0.8126 | 0.3734 | 0.1417 | 0.053* | |
H24B | 0.9311 | 0.4110 | 0.1092 | 0.053* | |
C25 | 0.9800 (2) | 0.32103 (13) | 0.17537 (13) | 0.0338 (5) | |
H25A | 1.0608 | 0.3126 | 0.1540 | 0.041* | |
H25B | 0.9962 | 0.3488 | 0.2222 | 0.041* | |
N6 | 0.98920 (18) | 0.45760 (10) | 0.43063 (11) | 0.0326 (4) | |
H6A | 0.9091 | 0.4402 | 0.4299 | 0.039* | |
H6B | 1.0236 | 0.4408 | 0.3888 | 0.039* | |
C26 | 1.0646 (2) | 0.43007 (12) | 0.49981 (13) | 0.0342 (5) | |
H26A | 1.1531 | 0.4444 | 0.4980 | 0.041* | |
H26B | 1.0609 | 0.3768 | 0.5010 | 0.041* | |
C27 | 0.9861 (2) | 0.53925 (12) | 0.42882 (13) | 0.0342 (5) | |
H27A | 0.9326 | 0.5555 | 0.3845 | 0.041* | |
H27B | 1.0715 | 0.5579 | 0.4243 | 0.041* | |
O13 | 0.81423 (18) | 0.18025 (13) | 0.37999 (12) | 0.0541 (5) | |
H13A | 0.7388 | 0.2009 | 0.3538 | 0.065* | |
H13B | 0.8441 | 0.1375 | 0.3547 | 0.065* | |
O14 | 0.08410 (19) | 0.14123 (13) | 0.47393 (13) | 0.0595 (5) | |
H14A | 0.1184 | 0.0932 | 0.4842 | 0.071* | |
H14B | 0.1450 | 0.1798 | 0.4842 | 0.071* | |
O15 | 0.9717 (2) | 0.30157 (13) | 0.37868 (15) | 0.0632 (6) | |
H15A | 0.9341 | 0.2546 | 0.3872 | 0.076* | |
H15B | 1.0587 | 0.2983 | 0.3668 | 0.076* | |
O16 | 0.7886 (2) | 0.39033 (17) | 0.29156 (13) | 0.0770 (7) | |
H16A | 0.7137 | 0.3922 | 0.3191 | 0.092* | |
H16B | 0.8550 | 0.3607 | 0.3162 | 0.092* | |
O17 | 0.9268 (3) | 0.04136 (14) | 0.31864 (17) | 0.0815 (8) | |
H17A | 0.9972 | 0.0680 | 0.2997 | 0.098* | |
H17B | 0.8921 | 0.0066 | 0.2814 | 0.098* | |
O18 | 0.8336 (3) | 0.00046 (13) | 0.47108 (16) | 0.0729 (7) | |
H18A | 0.7551 | 0.0262 | 0.4744 | 0.087* | |
H18B | 0.8786 | 0.0151 | 0.4284 | 0.087* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
In1 | 0.02250 (8) | 0.02853 (8) | 0.02525 (8) | 0.00242 (5) | 0.00605 (5) | 0.00403 (5) |
O1 | 0.0333 (8) | 0.0398 (9) | 0.0534 (10) | −0.0038 (7) | −0.0158 (7) | 0.0085 (8) |
O2 | 0.0342 (8) | 0.0299 (8) | 0.0479 (10) | −0.0017 (6) | 0.0013 (7) | 0.0041 (7) |
O3 | 0.0335 (8) | 0.0437 (10) | 0.0506 (10) | 0.0064 (7) | −0.0085 (7) | 0.0124 (8) |
O4 | 0.0260 (7) | 0.0365 (8) | 0.0260 (7) | 0.0026 (6) | −0.0005 (6) | 0.0012 (6) |
O5 | 0.0426 (9) | 0.0460 (10) | 0.0386 (9) | 0.0197 (8) | 0.0113 (7) | 0.0063 (7) |
O6 | 0.0355 (8) | 0.0345 (8) | 0.0258 (7) | 0.0090 (6) | 0.0072 (6) | −0.0004 (6) |
O7 | 0.0341 (9) | 0.0704 (13) | 0.0376 (9) | 0.0176 (8) | 0.0151 (7) | 0.0001 (8) |
O8 | 0.0303 (8) | 0.0411 (9) | 0.0307 (8) | 0.0073 (6) | 0.0094 (6) | 0.0054 (6) |
O9 | 0.0480 (11) | 0.0620 (13) | 0.0625 (13) | 0.0048 (9) | 0.0373 (10) | 0.0086 (10) |
O10 | 0.0278 (7) | 0.0413 (9) | 0.0386 (9) | −0.0024 (7) | 0.0116 (6) | 0.0062 (7) |
O11 | 0.0341 (9) | 0.0651 (13) | 0.0584 (12) | −0.0190 (9) | 0.0078 (8) | −0.0174 (10) |
O12 | 0.0320 (8) | 0.0476 (10) | 0.0364 (8) | −0.0116 (7) | 0.0079 (6) | −0.0060 (7) |
N1 | 0.0275 (8) | 0.0266 (8) | 0.0301 (8) | 0.0032 (7) | 0.0113 (7) | 0.0048 (7) |
N2 | 0.0194 (7) | 0.0278 (8) | 0.0233 (8) | −0.0019 (6) | 0.0047 (6) | 0.0001 (6) |
N3 | 0.0262 (8) | 0.0331 (9) | 0.0290 (9) | 0.0051 (7) | 0.0040 (7) | 0.0010 (7) |
C1 | 0.0223 (9) | 0.0335 (10) | 0.0284 (10) | −0.0030 (8) | 0.0012 (7) | 0.0022 (8) |
C2 | 0.0340 (11) | 0.0338 (11) | 0.0390 (12) | −0.0018 (9) | −0.0011 (9) | −0.0008 (9) |
C3 | 0.0443 (13) | 0.0294 (11) | 0.0534 (15) | 0.0011 (10) | 0.0022 (11) | −0.0019 (10) |
C4 | 0.0387 (12) | 0.0335 (12) | 0.0442 (13) | 0.0069 (10) | −0.0011 (10) | 0.0048 (10) |
C5 | 0.0247 (9) | 0.0318 (10) | 0.0300 (10) | 0.0023 (8) | 0.0036 (8) | 0.0051 (8) |
C6 | 0.0259 (9) | 0.0335 (11) | 0.0307 (10) | −0.0008 (8) | 0.0030 (8) | 0.0067 (8) |
C7 | 0.0225 (9) | 0.0377 (11) | 0.0256 (9) | 0.0043 (8) | 0.0030 (7) | 0.0056 (8) |
C8 | 0.0230 (9) | 0.0277 (10) | 0.0273 (9) | −0.0013 (7) | 0.0043 (7) | 0.0001 (7) |
C9 | 0.0319 (10) | 0.0324 (11) | 0.0311 (11) | 0.0032 (8) | 0.0026 (8) | 0.0041 (8) |
C10 | 0.0367 (11) | 0.0389 (12) | 0.0237 (10) | −0.0018 (9) | 0.0032 (8) | 0.0037 (8) |
C11 | 0.0323 (10) | 0.0396 (12) | 0.0239 (10) | −0.0016 (9) | 0.0087 (8) | −0.0038 (8) |
C12 | 0.0223 (9) | 0.0311 (10) | 0.0250 (9) | −0.0025 (8) | 0.0056 (7) | −0.0014 (8) |
C13 | 0.0280 (9) | 0.0247 (9) | 0.0302 (10) | 0.0023 (8) | 0.0067 (8) | −0.0006 (8) |
C14 | 0.0236 (9) | 0.0358 (11) | 0.0304 (10) | 0.0009 (8) | 0.0067 (8) | −0.0036 (9) |
C15 | 0.0345 (11) | 0.0395 (12) | 0.0325 (11) | 0.0091 (9) | 0.0105 (9) | 0.0050 (9) |
C16 | 0.0618 (18) | 0.0661 (19) | 0.0379 (14) | 0.0068 (15) | 0.0200 (12) | −0.0065 (13) |
C17 | 0.082 (2) | 0.073 (2) | 0.0455 (16) | −0.0077 (18) | 0.0179 (15) | −0.0261 (15) |
C18 | 0.0559 (17) | 0.0557 (17) | 0.0468 (15) | −0.0095 (13) | 0.0049 (12) | −0.0186 (13) |
C19 | 0.0311 (10) | 0.0360 (11) | 0.0338 (11) | 0.0013 (9) | 0.0021 (8) | −0.0040 (9) |
C20 | 0.0293 (11) | 0.0412 (12) | 0.0403 (12) | 0.0095 (9) | 0.0168 (9) | 0.0139 (10) |
C21 | 0.0284 (10) | 0.0357 (11) | 0.0391 (12) | −0.0034 (9) | 0.0033 (9) | −0.0025 (9) |
N4 | 0.0270 (9) | 0.0417 (11) | 0.0324 (10) | 0.0045 (8) | −0.0017 (7) | 0.0030 (8) |
N5 | 0.0463 (12) | 0.0593 (14) | 0.0331 (10) | −0.0104 (10) | −0.0042 (9) | 0.0078 (10) |
C22 | 0.0256 (10) | 0.0380 (12) | 0.0510 (14) | 0.0044 (9) | 0.0042 (10) | −0.0086 (10) |
C23 | 0.0357 (12) | 0.0523 (14) | 0.0328 (12) | −0.0105 (11) | 0.0019 (9) | −0.0061 (10) |
C24 | 0.0475 (14) | 0.0383 (13) | 0.0449 (14) | 0.0013 (11) | −0.0015 (11) | 0.0025 (10) |
C25 | 0.0275 (10) | 0.0422 (12) | 0.0313 (11) | 0.0010 (9) | 0.0012 (8) | −0.0070 (9) |
N6 | 0.0319 (9) | 0.0333 (9) | 0.0336 (9) | −0.0013 (7) | 0.0091 (7) | −0.0070 (7) |
C26 | 0.0370 (11) | 0.0286 (10) | 0.0377 (12) | 0.0047 (9) | 0.0079 (9) | −0.0004 (9) |
C27 | 0.0372 (11) | 0.0324 (11) | 0.0339 (11) | 0.0022 (9) | 0.0088 (9) | 0.0022 (9) |
O13 | 0.0374 (9) | 0.0708 (14) | 0.0535 (11) | 0.0105 (9) | 0.0006 (8) | 0.0052 (10) |
O14 | 0.0394 (10) | 0.0612 (13) | 0.0782 (15) | −0.0063 (9) | 0.0076 (10) | 0.0068 (11) |
O15 | 0.0455 (11) | 0.0568 (12) | 0.0890 (17) | 0.0044 (10) | 0.0152 (11) | −0.0147 (12) |
O16 | 0.0647 (14) | 0.115 (2) | 0.0539 (13) | 0.0051 (14) | 0.0228 (11) | 0.0147 (14) |
O17 | 0.0816 (17) | 0.0699 (16) | 0.098 (2) | −0.0358 (13) | 0.0345 (15) | −0.0215 (14) |
O18 | 0.0776 (17) | 0.0550 (13) | 0.0861 (17) | 0.0149 (12) | 0.0074 (13) | −0.0033 (12) |
Geometric parameters (Å, º) top
In1—O4 | 2.2434 (14) | C16—C17 | 1.376 (5) |
In1—N2 | 2.2777 (16) | C16—H16C | 0.9300 |
In1—O10 | 2.2857 (15) | C17—C18 | 1.384 (4) |
In1—N3 | 2.3132 (18) | C17—H17C | 0.9300 |
In1—O6 | 2.3270 (15) | C18—C19 | 1.388 (3) |
In1—N1 | 2.3586 (18) | C18—H18C | 0.9300 |
In1—O12 | 2.4419 (16) | C19—C21 | 1.513 (3) |
In1—O8 | 2.4532 (15) | N4—C25 | 1.483 (3) |
In1—O2 | 2.7247 (15) | N4—C22 | 1.487 (3) |
O1—C6 | 1.262 (3) | N4—H4B | 0.9000 |
O2—C6 | 1.242 (3) | N4—H4C | 0.9000 |
O3—C7 | 1.243 (3) | N5—C24 | 1.472 (3) |
O4—C7 | 1.265 (3) | N5—C23 | 1.494 (3) |
O5—C13 | 1.253 (3) | N5—H5A | 0.9000 |
O6—C13 | 1.249 (3) | N5—H5B | 0.9000 |
O7—C14 | 1.244 (3) | C22—C23 | 1.500 (4) |
O8—C14 | 1.255 (3) | C22—H22A | 0.9700 |
O9—C20 | 1.234 (3) | C22—H22B | 0.9700 |
O10—C20 | 1.275 (3) | C23—H23A | 0.9700 |
O11—C21 | 1.245 (3) | C23—H23B | 0.9700 |
O12—C21 | 1.247 (3) | C24—C25 | 1.510 (3) |
N1—C5 | 1.336 (3) | C24—H24A | 0.9700 |
N1—C1 | 1.353 (3) | C24—H24B | 0.9700 |
N2—C8 | 1.339 (3) | C25—H25A | 0.9700 |
N2—C12 | 1.341 (3) | C25—H25B | 0.9700 |
N3—C19 | 1.331 (3) | N6—C26 | 1.485 (3) |
N3—C15 | 1.336 (3) | N6—C27 | 1.485 (3) |
C1—C2 | 1.395 (3) | N6—H6A | 0.9000 |
C1—C6 | 1.510 (3) | N6—H6B | 0.9000 |
C2—C3 | 1.382 (3) | C26—C27i | 1.511 (3) |
C2—H2A | 0.9300 | C26—H26A | 0.9700 |
C3—C4 | 1.381 (4) | C26—H26B | 0.9700 |
C3—H3A | 0.9300 | C27—C26i | 1.511 (3) |
C4—C5 | 1.382 (3) | C27—H27A | 0.9700 |
C4—H4A | 0.9300 | C27—H27B | 0.9700 |
C5—C7 | 1.506 (3) | O13—H13A | 0.9614 |
C8—C9 | 1.386 (3) | O13—H13B | 0.9613 |
C8—C13 | 1.514 (3) | O14—H14A | 0.9565 |
C9—C10 | 1.383 (3) | O14—H14B | 0.9582 |
C9—H9A | 0.9300 | O15—H15A | 0.9577 |
C10—C11 | 1.378 (3) | O15—H15B | 0.9589 |
C10—H10A | 0.9300 | O16—H16A | 0.9588 |
C11—C12 | 1.382 (3) | O16—H16B | 0.9586 |
C11—H11A | 0.9300 | O17—H17A | 0.9669 |
C12—C14 | 1.509 (3) | O17—H17B | 0.9609 |
C15—C16 | 1.386 (4) | O18—H18A | 0.9563 |
C15—C20 | 1.505 (4) | O18—H18B | 0.9581 |
| | | |
O4—In1—N2 | 138.25 (6) | O8—C14—C12 | 115.67 (17) |
O4—In1—O10 | 84.65 (6) | N3—C15—C16 | 121.2 (2) |
N2—In1—O10 | 134.58 (6) | N3—C15—C20 | 115.1 (2) |
O4—In1—N3 | 75.23 (6) | C16—C15—C20 | 123.7 (2) |
N2—In1—N3 | 125.20 (6) | C17—C16—C15 | 119.1 (3) |
O10—In1—N3 | 69.90 (6) | C17—C16—H16C | 120.4 |
O4—In1—O6 | 147.33 (5) | C15—C16—H16C | 120.4 |
N2—In1—O6 | 69.72 (5) | C16—C17—C18 | 119.7 (3) |
O10—In1—O6 | 77.14 (6) | C16—C17—H17C | 120.2 |
N3—In1—O6 | 73.12 (6) | C18—C17—H17C | 120.2 |
O4—In1—N1 | 70.41 (6) | C17—C18—C19 | 118.0 (3) |
N2—In1—N1 | 102.35 (6) | C17—C18—H18C | 121.0 |
O10—In1—N1 | 74.90 (6) | C19—C18—H18C | 121.0 |
N3—In1—N1 | 132.36 (6) | N3—C19—C18 | 122.1 (2) |
O6—In1—N1 | 128.39 (6) | N3—C19—C21 | 114.31 (19) |
O4—In1—O12 | 83.78 (6) | C18—C19—C21 | 123.5 (2) |
N2—In1—O12 | 75.20 (6) | O9—C20—O10 | 126.0 (2) |
O10—In1—O12 | 136.50 (6) | O9—C20—C15 | 117.9 (2) |
N3—In1—O12 | 66.60 (6) | O10—C20—C15 | 116.07 (19) |
O6—In1—O12 | 90.98 (6) | O11—C21—O12 | 127.1 (2) |
N1—In1—O12 | 137.87 (6) | O11—C21—C19 | 117.2 (2) |
O4—In1—O8 | 71.52 (5) | O12—C21—C19 | 115.68 (19) |
N2—In1—O8 | 67.67 (5) | C25—N4—C22 | 110.52 (18) |
O10—In1—O8 | 141.99 (6) | C25—N4—H4B | 109.5 |
N3—In1—O8 | 128.03 (6) | C22—N4—H4B | 109.5 |
O6—In1—O8 | 136.66 (5) | C25—N4—H4C | 109.5 |
N1—In1—O8 | 69.46 (6) | C22—N4—H4C | 109.5 |
O12—In1—O8 | 71.04 (6) | H4B—N4—H4C | 108.1 |
C7—O4—In1 | 120.61 (13) | C24—N5—C23 | 112.3 (2) |
C13—O6—In1 | 118.89 (13) | C24—N5—H5A | 109.1 |
C14—O8—In1 | 118.80 (13) | C23—N5—H5A | 109.1 |
C20—O10—In1 | 120.38 (14) | C24—N5—H5B | 109.1 |
C21—O12—In1 | 119.55 (14) | C23—N5—H5B | 109.1 |
C5—N1—C1 | 118.31 (19) | H5A—N5—H5B | 107.9 |
C5—N1—In1 | 115.00 (14) | N4—C22—C23 | 111.82 (19) |
C1—N1—In1 | 126.35 (14) | N4—C22—H22A | 109.3 |
C8—N2—C12 | 119.68 (17) | C23—C22—H22A | 109.3 |
C8—N2—In1 | 118.36 (13) | N4—C22—H22B | 109.3 |
C12—N2—In1 | 121.73 (13) | C23—C22—H22B | 109.3 |
C19—N3—C15 | 119.9 (2) | H22A—C22—H22B | 107.9 |
C19—N3—In1 | 122.35 (14) | N5—C23—C22 | 112.7 (2) |
C15—N3—In1 | 117.73 (15) | N5—C23—H23A | 109.1 |
N1—C1—C2 | 121.79 (19) | C22—C23—H23A | 109.1 |
N1—C1—C6 | 115.77 (19) | N5—C23—H23B | 109.1 |
C2—C1—C6 | 122.43 (19) | C22—C23—H23B | 109.1 |
C3—C2—C1 | 119.0 (2) | H23A—C23—H23B | 107.8 |
C3—C2—H2A | 120.5 | N5—C24—C25 | 110.7 (2) |
C1—C2—H2A | 120.5 | N5—C24—H24A | 109.5 |
C4—C3—C2 | 119.0 (2) | C25—C24—H24A | 109.5 |
C4—C3—H3A | 120.5 | N5—C24—H24B | 109.5 |
C2—C3—H3A | 120.5 | C25—C24—H24B | 109.5 |
C3—C4—C5 | 119.1 (2) | H24A—C24—H24B | 108.1 |
C3—C4—H4A | 120.5 | N4—C25—C24 | 109.33 (19) |
C5—C4—H4A | 120.5 | N4—C25—H25A | 109.8 |
N1—C5—C4 | 122.8 (2) | C24—C25—H25A | 109.8 |
N1—C5—C7 | 115.12 (19) | N4—C25—H25B | 109.8 |
C4—C5—C7 | 122.1 (2) | C24—C25—H25B | 109.8 |
O2—C6—O1 | 126.4 (2) | H25A—C25—H25B | 108.3 |
O2—C6—C1 | 117.18 (19) | C26—N6—C27 | 111.33 (18) |
O1—C6—C1 | 116.46 (19) | C26—N6—H6A | 109.4 |
O3—C7—O4 | 124.8 (2) | C27—N6—H6A | 109.4 |
O3—C7—C5 | 117.9 (2) | C26—N6—H6B | 109.4 |
O4—C7—C5 | 117.30 (18) | C27—N6—H6B | 109.4 |
N2—C8—C9 | 121.32 (19) | H6A—N6—H6B | 108.0 |
N2—C8—C13 | 114.87 (17) | N6—C26—C27i | 110.77 (18) |
C9—C8—C13 | 123.81 (19) | N6—C26—H26A | 109.5 |
C10—C9—C8 | 119.0 (2) | C27i—C26—H26A | 109.5 |
C10—C9—H9A | 120.5 | N6—C26—H26B | 109.5 |
C8—C9—H9A | 120.5 | C27i—C26—H26B | 109.5 |
C11—C10—C9 | 119.3 (2) | H26A—C26—H26B | 108.1 |
C11—C10—H10A | 120.3 | N6—C27—C26i | 111.08 (18) |
C9—C10—H10A | 120.3 | N6—C27—H27A | 109.4 |
C10—C11—C12 | 118.88 (19) | C26i—C27—H27A | 109.4 |
C10—C11—H11A | 120.6 | N6—C27—H27B | 109.4 |
C12—C11—H11A | 120.6 | C26i—C27—H27B | 109.4 |
N2—C12—C11 | 121.71 (19) | H27A—C27—H27B | 108.0 |
N2—C12—C14 | 115.55 (17) | H13A—O13—H13B | 112.5 |
C11—C12—C14 | 122.74 (18) | H14A—O14—H14B | 113.4 |
O6—C13—O5 | 125.84 (19) | H15A—O15—H15B | 113.2 |
O6—C13—C8 | 116.20 (18) | H16A—O16—H16B | 113.0 |
O5—C13—C8 | 117.96 (19) | H17A—O17—H17B | 110.7 |
O7—C14—O8 | 126.4 (2) | H18A—O18—H18B | 113.4 |
O7—C14—C12 | 117.9 (2) | | |
| | | |
N2—In1—O4—C7 | −76.20 (17) | N1—C1—C2—C3 | 1.5 (3) |
O10—In1—O4—C7 | 86.34 (16) | C6—C1—C2—C3 | −177.1 (2) |
N3—In1—O4—C7 | 156.94 (16) | C1—C2—C3—C4 | 2.0 (4) |
O6—In1—O4—C7 | 142.27 (15) | C2—C3—C4—C5 | −3.2 (4) |
N1—In1—O4—C7 | 10.49 (15) | C1—N1—C5—C4 | 2.5 (3) |
O12—In1—O4—C7 | −135.67 (16) | In1—N1—C5—C4 | −171.13 (18) |
O8—In1—O4—C7 | −63.62 (15) | C1—N1—C5—C7 | −176.28 (17) |
O4—In1—O6—C13 | 166.74 (14) | In1—N1—C5—C7 | 10.1 (2) |
N2—In1—O6—C13 | 12.94 (15) | C3—C4—C5—N1 | 0.9 (4) |
O10—In1—O6—C13 | −135.49 (16) | C3—C4—C5—C7 | 179.7 (2) |
N3—In1—O6—C13 | 151.91 (17) | N1—C1—C6—O2 | 5.9 (3) |
N1—In1—O6—C13 | −76.95 (17) | C2—C1—C6—O2 | −175.4 (2) |
O12—In1—O6—C13 | 86.76 (16) | N1—C1—C6—O1 | −173.03 (19) |
O8—In1—O6—C13 | 23.85 (19) | C2—C1—C6—O1 | 5.6 (3) |
O4—In1—O8—C14 | −169.55 (17) | In1—O4—C7—O3 | 173.06 (17) |
N2—In1—O8—C14 | 1.43 (15) | In1—O4—C7—C5 | −9.0 (2) |
O10—In1—O8—C14 | 136.41 (16) | N1—C5—C7—O3 | 176.71 (19) |
N3—In1—O8—C14 | −116.60 (16) | C4—C5—C7—O3 | −2.1 (3) |
O6—In1—O8—C14 | −9.6 (2) | N1—C5—C7—O4 | −1.3 (3) |
N1—In1—O8—C14 | 115.06 (17) | C4—C5—C7—O4 | 179.9 (2) |
O12—In1—O8—C14 | −79.89 (16) | C12—N2—C8—C9 | 1.8 (3) |
O4—In1—O10—C20 | 84.37 (17) | In1—N2—C8—C9 | −172.86 (16) |
N2—In1—O10—C20 | −111.92 (17) | C12—N2—C8—C13 | −178.57 (17) |
N3—In1—O10—C20 | 8.16 (16) | In1—N2—C8—C13 | 6.8 (2) |
O6—In1—O10—C20 | −68.33 (17) | N2—C8—C9—C10 | 0.3 (3) |
N1—In1—O10—C20 | 155.50 (18) | C13—C8—C9—C10 | −179.3 (2) |
O12—In1—O10—C20 | 9.2 (2) | C8—C9—C10—C11 | −2.5 (3) |
O8—In1—O10—C20 | 134.82 (16) | C9—C10—C11—C12 | 2.5 (3) |
O4—In1—O12—C21 | −66.67 (18) | C8—N2—C12—C11 | −1.7 (3) |
N2—In1—O12—C21 | 149.72 (19) | In1—N2—C12—C11 | 172.71 (16) |
O10—In1—O12—C21 | 8.8 (2) | C8—N2—C12—C14 | 177.68 (18) |
N3—In1—O12—C21 | 9.90 (17) | In1—N2—C12—C14 | −7.9 (2) |
O6—In1—O12—C21 | 81.01 (18) | C10—C11—C12—N2 | −0.4 (3) |
N1—In1—O12—C21 | −118.13 (17) | C10—C11—C12—C14 | −179.8 (2) |
O8—In1—O12—C21 | −139.23 (19) | In1—O6—C13—O5 | 166.35 (18) |
O4—In1—N1—C5 | −10.57 (14) | In1—O6—C13—C8 | −13.9 (2) |
N2—In1—N1—C5 | 126.55 (14) | N2—C8—C13—O6 | 4.8 (3) |
O10—In1—N1—C5 | −100.19 (15) | C9—C8—C13—O6 | −175.5 (2) |
N3—In1—N1—C5 | −56.89 (17) | N2—C8—C13—O5 | −175.44 (19) |
O6—In1—N1—C5 | −159.67 (13) | C9—C8—C13—O5 | 4.2 (3) |
O12—In1—N1—C5 | 45.05 (18) | In1—O8—C14—O7 | 174.66 (19) |
O8—In1—N1—C5 | 66.38 (14) | In1—O8—C14—C12 | −5.6 (2) |
O4—In1—N1—C1 | 176.37 (17) | N2—C12—C14—O7 | −171.5 (2) |
N2—In1—N1—C1 | −46.51 (17) | C11—C12—C14—O7 | 7.9 (3) |
O10—In1—N1—C1 | 86.74 (16) | N2—C12—C14—O8 | 8.7 (3) |
N3—In1—N1—C1 | 130.04 (16) | C11—C12—C14—O8 | −171.9 (2) |
O6—In1—N1—C1 | 27.27 (18) | C19—N3—C15—C16 | 2.0 (3) |
O12—In1—N1—C1 | −128.02 (16) | In1—N3—C15—C16 | −176.1 (2) |
O8—In1—N1—C1 | −106.69 (17) | C19—N3—C15—C20 | −178.30 (19) |
O4—In1—N2—C8 | −168.79 (13) | In1—N3—C15—C20 | 3.6 (2) |
O10—In1—N2—C8 | 36.01 (18) | N3—C15—C16—C17 | −1.4 (4) |
N3—In1—N2—C8 | −60.01 (16) | C20—C15—C16—C17 | 178.9 (3) |
O6—In1—N2—C8 | −9.77 (14) | C15—C16—C17—C18 | −0.1 (5) |
N1—In1—N2—C8 | 116.88 (14) | C16—C17—C18—C19 | 1.1 (5) |
O12—In1—N2—C8 | −106.45 (15) | C15—N3—C19—C18 | −0.9 (4) |
O8—In1—N2—C8 | 178.30 (16) | In1—N3—C19—C18 | 177.1 (2) |
O4—In1—N2—C12 | 16.68 (19) | C15—N3—C19—C21 | 179.5 (2) |
O10—In1—N2—C12 | −138.51 (14) | In1—N3—C19—C21 | −2.5 (3) |
N3—In1—N2—C12 | 125.46 (15) | C17—C18—C19—N3 | −0.6 (5) |
O6—In1—N2—C12 | 175.71 (16) | C17—C18—C19—C21 | 178.9 (3) |
N1—In1—N2—C12 | −57.65 (15) | In1—O10—C20—O9 | 171.9 (2) |
O12—In1—N2—C12 | 79.02 (15) | In1—O10—C20—C15 | −9.2 (3) |
O8—In1—N2—C12 | 3.78 (14) | N3—C15—C20—O9 | −177.5 (2) |
O4—In1—N3—C19 | 86.50 (17) | C16—C15—C20—O9 | 2.3 (4) |
N2—In1—N3—C19 | −52.82 (18) | N3—C15—C20—O10 | 3.5 (3) |
O10—In1—N3—C19 | 176.14 (18) | C16—C15—C20—O10 | −176.8 (2) |
O6—In1—N3—C19 | −101.72 (17) | In1—O12—C21—O11 | 164.9 (2) |
N1—In1—N3—C19 | 131.30 (16) | In1—O12—C21—C19 | −14.5 (3) |
O12—In1—N3—C19 | −3.05 (16) | N3—C19—C21—O11 | −168.2 (2) |
O8—In1—N3—C19 | 34.98 (19) | C18—C19—C21—O11 | 12.3 (4) |
O4—In1—N3—C15 | −95.46 (16) | N3—C19—C21—O12 | 11.3 (3) |
N2—In1—N3—C15 | 125.23 (15) | C18—C19—C21—O12 | −168.3 (3) |
O10—In1—N3—C15 | −5.81 (15) | C25—N4—C22—C23 | −55.8 (2) |
O6—In1—N3—C15 | 76.33 (16) | C24—N5—C23—C22 | −49.9 (3) |
N1—In1—N3—C15 | −50.65 (18) | N4—C22—C23—N5 | 50.1 (3) |
O12—In1—N3—C15 | 175.00 (17) | C23—N5—C24—C25 | 54.7 (3) |
O8—In1—N3—C15 | −146.98 (14) | C22—N4—C25—C24 | 60.2 (2) |
C5—N1—C1—C2 | −3.7 (3) | N5—C24—C25—N4 | −59.9 (3) |
In1—N1—C1—C2 | 169.13 (16) | C27—N6—C26—C27i | 55.9 (3) |
C5—N1—C1—C6 | 174.95 (18) | C26—N6—C27—C26i | −56.0 (3) |
In1—N1—C1—C6 | −12.2 (2) | | |
Symmetry code: (i) −x+2, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4B···O7 | 0.90 | 2.01 | 2.791 (3) | 145 |
N4—H4C···O1ii | 0.90 | 1.84 | 2.702 (3) | 159 |
N5—H5A···O14iii | 0.90 | 1.95 | 2.792 (3) | 155 |
N5—H5B···O3iv | 0.90 | 1.99 | 2.800 (3) | 149 |
N6—H6A···O11 | 0.90 | 1.94 | 2.780 (3) | 155 |
N6—H6B···O5ii | 0.90 | 2.00 | 2.836 (3) | 154 |
O13—H13A···O8 | 0.96 | 1.82 | 2.761 (3) | 166 |
O13—H13B···O17 | 0.96 | 2.08 | 3.026 (4) | 170 |
O14—H14A···O18v | 0.96 | 1.93 | 2.861 (3) | 165 |
O14—H14B···O10 | 0.96 | 1.85 | 2.798 (3) | 168 |
O15—H15A···O13 | 0.96 | 1.85 | 2.761 (3) | 159 |
O15—H15B···O2ii | 0.96 | 2.00 | 2.870 (3) | 150 |
O16—H16A···O12 | 0.96 | 1.96 | 2.868 (3) | 157 |
O16—H16B···O15 | 0.96 | 1.91 | 2.862 (3) | 171 |
O17—H17A···O1ii | 0.97 | 1.91 | 2.817 (3) | 156 |
O17—H17B···O5vi | 0.96 | 1.96 | 2.901 (3) | 167 |
O18—H18A···O3 | 0.96 | 1.91 | 2.826 (3) | 159 |
O18—H18B···O17 | 0.96 | 2.09 | 3.023 (4) | 164 |
Symmetry codes: (ii) x+1, y, z; (iii) x+1, −y+1/2, z−1/2; (iv) x, −y+1/2, z−1/2; (v) −x+1, −y, −z+1; (vi) −x+1, y−1/2, −z+1/2. |