Tris(piperazinediium) bis­[tris­(pyridine-2,6-dicarboxyl­ato)-κ⁶O,N,O′;κ²O,N-indate(III)] dodeca­hydrate

The asymmetric unit of the title compound, (C₄H₁₂N₂)₃[In(C₇H₃NO₄)₃]₂·12H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](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

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Computing details

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

Crystal data

(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) Å^3	0.30 × 0.30 × 0.20 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: mixed
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.04P)^2 + 3.2P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C27^i	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—C26^i	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—C27^i	110.77 (18)
C9—C8—C13	123.81 (19)	N6—C26—H26A	109.5
C10—C9—C8	119.0 (2)	C27^i—C26—H26A	109.5
C10—C9—H9A	120.5	N6—C26—H26B	109.5
C8—C9—H9A	120.5	C27^i—C26—H26B	109.5
C11—C10—C9	119.3 (2)	H26A—C26—H26B	108.1
C11—C10—H10A	120.3	N6—C27—C26^i	111.08 (18)
C9—C10—H10A	120.3	N6—C27—H27A	109.4
C10—C11—C12	118.88 (19)	C26^i—C27—H27A	109.4
C10—C11—H11A	120.6	N6—C27—H27B	109.4
C12—C11—H11A	120.6	C26^i—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—C27^i	55.9 (3)
C5—N1—C1—C6	174.95 (18)	C26—N6—C27—C26^i	−56.0 (3)
In1—N1—C1—C6	−12.2 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

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···O1^ii	0.90	1.84	2.702 (3)	159
N5—H5A···O14^iii	0.90	1.95	2.792 (3)	155
N5—H5B···O3^iv	0.90	1.99	2.800 (3)	149
N6—H6A···O11	0.90	1.94	2.780 (3)	155
N6—H6B···O5^ii	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···O18^v	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···O2^ii	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···O1^ii	0.97	1.91	2.817 (3)	156
O17—H17B···O5^vi	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.