Dichlorido[tris-(benzimidazol-2-ylmeth-yl)amine]-indium(III) chloride ethanol solvate dihydrate.

In the title complex, [InCl(2)(C(24)H(21)N(7))]Cl·C(2)H(5)OH·2H(2)O, the In(III) ion is coordinated by four N atoms from the tris-(benz-imidazol-2-ylmeth-yl)amine (NTB) ligand and two Cl atoms in a distorted octa-hedral environment. In the crystal structure, inter-molecular N-H⋯O, O-H⋯O, O-H⋯Cl and weak C-H⋯Cl hydrogen bonds connect the cations, anions and solvent mol-ecules into a three-dimensional network. The ethanol solvent mol-ecule is disordered over two sites with refined occupancies of 0.54 (2) and 0.46 (2).

Related literature

For background information and the applications of indium complexes, see: Green et al. (2005 ▶); Krivokapic et al. (2001 ▶); Lu et al. (2005 ▶); Sun et al. (2009 ▶); Vagin et al. (2003 ▶). For the synthetic procedure, see: Hendriks et al. (1982 ▶).

Experimental

Crystal data

[InCl2(C24H21N7)]Cl·C2H6O·2H2O

M = 710.75

Monoclinic,

a = 10.4152 (10) Å

b = 13.7394 (13) Å

c = 21.903 (2) Å

β = 103.75°

V = 3044.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.08 mm−1

T = 298 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.846, T max = 0.900

22634 measured reflections

7526 independent reflections

6941 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.089

S = 1.15

7526 reflections

403 parameters

6 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.95 e Å−3

Δρmin = −0.55 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029806/lh5092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029806/lh5092Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[InCl2(C24H21N7)]Cl·C2H6O·2H2O	F(000) = 1440
Mr = 710.75	Dx = 1.551 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5767 reflections
a = 10.4152 (10) Å	θ = 2.4–28.3°
b = 13.7394 (13) Å	µ = 1.08 mm−1
c = 21.903 (2) Å	T = 298 K
β = 103.75°	Block, colorless
V = 3044.4 (5) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker SMART CCD diffractometer	7526 independent reflections
Radiation source: fine-focus sealed tube	6941 reflections with I > 2σ(I)
graphite	Rint = 0.033
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −13→13
Tmin = 0.846, Tmax = 0.900	k = −13→18
22634 measured reflections	l = −28→29

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0382P)2 + 1.3452P] where P = (Fo2 + 2Fc2)/3
7526 reflections	(Δ/σ)max < 0.001
403 parameters	Δρmax = 0.95 e Å−3
6 restraints	Δρmin = −0.55 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
In1	0.447613 (16)	0.710677 (12)	0.302721 (8)	0.02890 (6)
C1	0.6729 (2)	0.85480 (19)	0.37586 (13)	0.0380 (6)
H1A	0.7209	0.8873	0.4137	0.046*
H1B	0.6774	0.8950	0.3400	0.046*
C2	0.7324 (2)	0.7572 (2)	0.37027 (12)	0.0354 (5)
C3	0.7475 (2)	0.6060 (2)	0.34430 (12)	0.0352 (5)
C4	0.7229 (3)	0.5111 (2)	0.32325 (13)	0.0419 (6)
H4	0.6393	0.4915	0.3011	0.050*
C5	0.8274 (3)	0.4474 (2)	0.33659 (15)	0.0547 (8)
H5	0.8143	0.3830	0.3234	0.066*
C6	0.9521 (3)	0.4770 (3)	0.36927 (18)	0.0671 (10)
H6	1.0206	0.4318	0.3769	0.081*
C7	0.9781 (3)	0.5705 (3)	0.39078 (17)	0.0615 (9)
H7	1.0621	0.5896	0.4127	0.074*
C8	0.8723 (3)	0.6355 (2)	0.37807 (13)	0.0422 (6)
C9	0.5226 (3)	0.8079 (2)	0.44197 (12)	0.0395 (6)
H9A	0.4754	0.8572	0.4596	0.047*
H9B	0.6107	0.8025	0.4691	0.047*
C10	0.4529 (3)	0.71260 (19)	0.44155 (12)	0.0352 (5)
C11	0.3720 (2)	0.5684 (2)	0.41656 (12)	0.0354 (5)
C12	0.3344 (3)	0.4790 (2)	0.38883 (14)	0.0432 (6)
H12	0.3404	0.4655	0.3480	0.052*
C13	0.2875 (3)	0.4107 (2)	0.42440 (16)	0.0521 (8)
H13	0.2617	0.3499	0.4072	0.063*
C14	0.2782 (3)	0.4307 (3)	0.48525 (17)	0.0551 (8)
H14	0.2449	0.3831	0.5074	0.066*
C15	0.3163 (3)	0.5182 (3)	0.51383 (15)	0.0521 (8)
H15	0.3101	0.5310	0.5547	0.063*
C16	0.3648 (3)	0.5868 (2)	0.47842 (13)	0.0397 (6)
C17	0.4499 (3)	0.92644 (19)	0.35714 (13)	0.0383 (6)
H17A	0.4807	0.9600	0.3244	0.046*
H17B	0.4554	0.9710	0.3920	0.046*
C18	0.3108 (3)	0.8943 (2)	0.33274 (12)	0.0363 (5)
C19	0.1407 (3)	0.8058 (2)	0.28851 (12)	0.0366 (6)
C20	0.0541 (3)	0.7343 (2)	0.25857 (15)	0.0478 (7)
H20	0.0843	0.6735	0.2495	0.057*
C21	−0.0787 (3)	0.7572 (3)	0.24282 (16)	0.0566 (8)
H21	−0.1390	0.7109	0.2225	0.068*
C22	−0.1246 (3)	0.8477 (3)	0.25658 (16)	0.0566 (9)
H22	−0.2148	0.8604	0.2448	0.068*
C23	−0.0411 (3)	0.9185 (3)	0.28691 (15)	0.0526 (8)
H23	−0.0726	0.9784	0.2967	0.063*
C24	0.0937 (3)	0.8965 (2)	0.30258 (13)	0.0408 (6)
C25	1.061 (3)	0.7795 (16)	0.5779 (14)	0.163 (9)	0.54 (2)
H25A	1.0751	0.7203	0.5572	0.244*	0.54 (2)
H25B	1.0014	0.7672	0.6045	0.244*	0.54 (2)
H25C	1.1435	0.8028	0.6029	0.244*	0.54 (2)
C26	1.0026 (12)	0.8538 (10)	0.5302 (6)	0.101 (5)	0.54 (2)
H26A	0.9071	0.8488	0.5224	0.121*	0.54 (2)
H26B	1.0271	0.9174	0.5485	0.121*	0.54 (2)
C25'	1.058 (3)	0.8492 (17)	0.5828 (15)	0.140 (9)	0.46 (2)
H25D	1.1351	0.8561	0.6166	0.209*	0.46 (2)
H25E	0.9843	0.8298	0.5993	0.209*	0.46 (2)
H25F	1.0383	0.9104	0.5613	0.209*	0.46 (2)
C26'	1.0832 (19)	0.7717 (14)	0.5365 (8)	0.115 (7)	0.46 (2)
H26C	1.1710	0.7449	0.5522	0.138*	0.46 (2)
H26D	1.0201	0.7192	0.5346	0.138*	0.46 (2)
Cl1	0.35306 (7)	0.57777 (5)	0.23656 (3)	0.04797 (17)
Cl2	0.49870 (7)	0.81165 (5)	0.21877 (3)	0.04437 (16)
Cl3	0.30232 (9)	0.53452 (6)	0.00493 (4)	0.0574 (2)
N1	0.53335 (19)	0.83983 (15)	0.37826 (9)	0.0316 (4)
N2	0.6621 (2)	0.68466 (16)	0.34018 (10)	0.0341 (5)
N3	0.8591 (2)	0.73183 (19)	0.39420 (12)	0.0431 (6)
H3	0.9204	0.7686	0.4155	0.052*
N4	0.4266 (2)	0.65021 (16)	0.39445 (10)	0.0339 (5)
N5	0.4164 (2)	0.67908 (18)	0.49227 (11)	0.0412 (5)
H5A	0.4238	0.7095	0.5272	0.049*
N6	0.2781 (2)	0.80711 (16)	0.30802 (10)	0.0350 (5)
N7	0.2042 (2)	0.95009 (17)	0.33077 (11)	0.0421 (5)
H7A	0.2045	1.0087	0.3446	0.050*
O2	0.4684 (3)	0.6888 (2)	0.09360 (12)	0.0655 (7)
H2A	0.416 (3)	0.644 (2)	0.0807 (16)	0.079*
H2B	0.460 (4)	0.706 (3)	0.1286 (11)	0.079*
O3	0.7331 (3)	0.6250 (2)	0.10069 (13)	0.0683 (7)
H3A	0.662 (3)	0.653 (3)	0.0997 (17)	0.082*
H3B	0.726 (4)	0.595 (3)	0.0673 (13)	0.082*
O1	1.0355 (12)	0.8506 (10)	0.4735 (6)	0.079 (3)	0.54 (2)
H1	1.1026	0.8828	0.4753	0.118*	0.54 (2)
O1'	1.0731 (18)	0.8074 (14)	0.4765 (8)	0.097 (5)	0.46 (2)
H1'	1.0988	0.8639	0.4787	0.146*	0.46 (2)

	U11	U22	U33	U12	U13	U23
In1	0.02836 (9)	0.02947 (10)	0.02775 (10)	0.00063 (6)	0.00442 (6)	−0.00344 (6)
C1	0.0342 (13)	0.0353 (14)	0.0431 (15)	−0.0046 (10)	0.0066 (11)	−0.0048 (11)
C2	0.0305 (12)	0.0396 (14)	0.0356 (13)	−0.0011 (10)	0.0065 (10)	−0.0018 (11)
C3	0.0306 (12)	0.0425 (15)	0.0323 (12)	0.0054 (10)	0.0071 (10)	−0.0006 (11)
C4	0.0411 (14)	0.0450 (16)	0.0378 (14)	0.0049 (12)	0.0054 (11)	−0.0067 (12)
C5	0.0592 (19)	0.0491 (19)	0.0544 (19)	0.0177 (15)	0.0111 (15)	−0.0086 (15)
C6	0.0522 (19)	0.066 (2)	0.079 (3)	0.0278 (17)	0.0071 (18)	−0.0071 (19)
C7	0.0341 (15)	0.074 (2)	0.070 (2)	0.0131 (15)	0.0005 (15)	−0.0025 (19)
C8	0.0337 (13)	0.0485 (17)	0.0437 (15)	0.0030 (12)	0.0080 (11)	−0.0016 (13)
C9	0.0470 (15)	0.0390 (15)	0.0315 (13)	−0.0032 (12)	0.0076 (11)	−0.0066 (11)
C10	0.0343 (12)	0.0371 (14)	0.0329 (13)	0.0027 (10)	0.0052 (10)	0.0017 (10)
C11	0.0311 (12)	0.0368 (14)	0.0372 (13)	0.0009 (10)	0.0058 (10)	0.0053 (11)
C12	0.0445 (15)	0.0382 (15)	0.0450 (16)	−0.0008 (12)	0.0066 (12)	0.0024 (12)
C13	0.0454 (16)	0.0393 (17)	0.068 (2)	−0.0067 (13)	0.0066 (15)	0.0069 (15)
C14	0.0465 (17)	0.053 (2)	0.065 (2)	−0.0027 (14)	0.0120 (15)	0.0229 (16)
C15	0.0501 (17)	0.064 (2)	0.0441 (16)	0.0020 (15)	0.0152 (14)	0.0172 (15)
C16	0.0370 (13)	0.0422 (15)	0.0389 (14)	0.0023 (11)	0.0067 (11)	0.0070 (12)
C17	0.0402 (14)	0.0308 (13)	0.0423 (15)	0.0016 (11)	0.0066 (11)	−0.0046 (11)
C18	0.0373 (13)	0.0352 (14)	0.0353 (13)	0.0056 (10)	0.0066 (10)	−0.0017 (11)
C19	0.0321 (12)	0.0443 (16)	0.0340 (13)	0.0044 (11)	0.0088 (10)	0.0032 (11)
C20	0.0416 (15)	0.0513 (18)	0.0489 (17)	−0.0063 (13)	0.0074 (13)	−0.0049 (14)
C21	0.0365 (15)	0.078 (2)	0.0540 (19)	−0.0108 (15)	0.0074 (14)	−0.0010 (17)
C22	0.0332 (14)	0.081 (3)	0.0549 (19)	0.0072 (15)	0.0090 (13)	0.0102 (17)
C23	0.0444 (16)	0.062 (2)	0.0530 (18)	0.0169 (14)	0.0144 (14)	0.0100 (15)
C24	0.0380 (14)	0.0466 (16)	0.0379 (14)	0.0071 (12)	0.0095 (11)	0.0036 (12)
C25	0.186 (19)	0.160 (19)	0.153 (19)	0.005 (18)	0.063 (15)	0.027 (19)
C26	0.097 (7)	0.124 (10)	0.081 (9)	0.009 (7)	0.022 (6)	−0.021 (6)
C25'	0.132 (14)	0.16 (2)	0.14 (2)	−0.010 (17)	0.058 (13)	0.017 (18)
C26'	0.114 (12)	0.120 (14)	0.102 (12)	−0.042 (10)	0.010 (9)	0.017 (10)
Cl1	0.0516 (4)	0.0418 (4)	0.0476 (4)	−0.0079 (3)	0.0061 (3)	−0.0161 (3)
Cl2	0.0537 (4)	0.0435 (4)	0.0372 (3)	−0.0036 (3)	0.0134 (3)	0.0040 (3)
Cl3	0.0627 (5)	0.0534 (5)	0.0556 (5)	0.0060 (4)	0.0133 (4)	0.0069 (4)
N1	0.0316 (10)	0.0297 (11)	0.0327 (11)	−0.0017 (8)	0.0060 (8)	−0.0022 (8)
N2	0.0304 (10)	0.0347 (11)	0.0360 (11)	0.0009 (8)	0.0053 (9)	−0.0045 (9)
N3	0.0291 (11)	0.0495 (15)	0.0471 (14)	−0.0048 (10)	0.0015 (10)	−0.0036 (11)
N4	0.0365 (11)	0.0338 (12)	0.0309 (11)	−0.0014 (9)	0.0071 (9)	0.0001 (9)
N5	0.0473 (13)	0.0463 (14)	0.0311 (11)	0.0003 (11)	0.0113 (10)	−0.0002 (10)
N6	0.0323 (10)	0.0351 (12)	0.0365 (11)	0.0030 (9)	0.0057 (9)	−0.0032 (9)
N7	0.0437 (12)	0.0378 (13)	0.0440 (13)	0.0089 (10)	0.0090 (10)	−0.0048 (10)
O2	0.087 (2)	0.0677 (18)	0.0421 (13)	−0.0024 (13)	0.0163 (13)	−0.0034 (12)
O3	0.0772 (17)	0.0528 (16)	0.0736 (18)	−0.0008 (13)	0.0156 (15)	0.0047 (13)
O1	0.073 (5)	0.092 (8)	0.068 (5)	−0.036 (5)	0.010 (4)	−0.017 (5)
O1'	0.092 (9)	0.094 (10)	0.087 (6)	−0.042 (7)	−0.015 (6)	0.005 (8)

In1—N2	2.218 (2)	C17—N1	1.481 (3)
In1—N4	2.232 (2)	C17—C18	1.487 (4)
In1—N6	2.233 (2)	C17—H17A	0.9700
In1—Cl1	2.3928 (7)	C17—H17B	0.9700
In1—N1	2.446 (2)	C18—N6	1.326 (3)
In1—Cl2	2.4604 (7)	C18—N7	1.341 (3)
C1—N1	1.481 (3)	C19—C20	1.389 (4)
C1—C2	1.495 (4)	C19—N6	1.392 (3)
C1—H1A	0.9700	C19—C24	1.399 (4)
C1—H1B	0.9700	C20—C21	1.380 (4)
C2—N2	1.317 (3)	C20—H20	0.9300
C2—N3	1.344 (3)	C21—C22	1.391 (5)
C3—C4	1.386 (4)	C21—H21	0.9300
C3—N2	1.390 (3)	C22—C23	1.367 (5)
C3—C8	1.394 (4)	C22—H22	0.9300
C4—C5	1.374 (4)	C23—C24	1.397 (4)
C4—H4	0.9300	C23—H23	0.9300
C5—C6	1.386 (5)	C24—N7	1.383 (4)
C5—H5	0.9300	C25—C26	1.48 (3)
C6—C7	1.374 (5)	C25—H25A	0.9600
C6—H6	0.9300	C25—H25B	0.9600
C7—C8	1.393 (4)	C25—H25C	0.9600
C7—H7	0.9300	C26—O1	1.366 (17)
C8—N3	1.386 (4)	C26—H26A	0.9700
C9—N1	1.492 (3)	C26—H26B	0.9700
C9—C10	1.495 (4)	C25'—C26'	1.54 (4)
C9—H9A	0.9700	C25'—H25D	0.9600
C9—H9B	0.9700	C25'—H25E	0.9600
C10—N4	1.319 (3)	C25'—H25F	0.9600
C10—N5	1.338 (3)	C26'—O1'	1.38 (2)
C11—C12	1.385 (4)	C26'—H26C	0.9700
C11—N4	1.397 (3)	C26'—H26D	0.9700
C11—C16	1.398 (4)	N3—H3	0.8600
C12—C13	1.380 (4)	N5—H5A	0.8600
C12—H12	0.9300	N7—H7A	0.8600
C13—C14	1.387 (5)	O2—H2A	0.823 (17)
C13—H13	0.9300	O2—H2B	0.825 (18)
C14—C15	1.369 (5)	O3—H3A	0.823 (18)
C14—H14	0.9300	O3—H3B	0.829 (18)
C15—C16	1.390 (4)	O1—H1	0.8200
C15—H15	0.9300	O1'—H1'	0.8195
C16—N5	1.382 (4)
N2—In1—N4	84.98 (8)	C21—C20—C19	117.1 (3)
N2—In1—N6	144.67 (8)	C21—C20—H20	121.4
N4—In1—N6	85.77 (8)	C19—C20—H20	121.4
N2—In1—Cl1	109.53 (6)	C20—C21—C22	121.7 (3)
N4—In1—Cl1	98.44 (6)	C20—C21—H21	119.1
N6—In1—Cl1	105.52 (6)	C22—C21—H21	119.1
N2—In1—N1	72.12 (7)	C23—C22—C21	122.0 (3)
N4—In1—N1	76.07 (7)	C23—C22—H22	119.0
N6—In1—N1	72.56 (7)	C21—C22—H22	119.0
Cl1—In1—N1	174.22 (5)	C22—C23—C24	116.8 (3)
N2—In1—Cl2	89.41 (6)	C22—C23—H23	121.6
N4—In1—Cl2	165.30 (6)	C24—C23—H23	121.6
N6—In1—Cl2	91.06 (6)	N7—C24—C23	132.5 (3)
Cl1—In1—Cl2	96.24 (3)	N7—C24—C19	105.9 (2)
N1—In1—Cl2	89.28 (5)	C23—C24—C19	121.5 (3)
N1—C1—C2	107.9 (2)	O1—C26—C25	118.0 (15)
N1—C1—H1A	110.1	O1—C26—H26A	107.8
C2—C1—H1A	110.1	C25—C26—H26A	107.8
N1—C1—H1B	110.1	O1—C26—H26B	107.8
C2—C1—H1B	110.1	C25—C26—H26B	107.8
H1A—C1—H1B	108.4	H26A—C26—H26B	107.1
N2—C2—N3	112.1 (2)	C26'—C25'—H25D	109.5
N2—C2—C1	121.8 (2)	C26'—C25'—H25E	109.5
N3—C2—C1	126.0 (2)	H25D—C25'—H25E	109.5
C4—C3—N2	130.2 (2)	C26'—C25'—H25F	109.5
C4—C3—C8	121.7 (2)	H25D—C25'—H25F	109.5
N2—C3—C8	108.1 (2)	H25E—C25'—H25F	109.5
C5—C4—C3	117.0 (3)	O1'—C26'—C25'	113.3 (18)
C5—C4—H4	121.5	O1'—C26'—H26C	108.9
C3—C4—H4	121.5	C25'—C26'—H26C	108.9
C4—C5—C6	121.4 (3)	O1'—C26'—H26D	108.9
C4—C5—H5	119.3	C25'—C26'—H26D	108.9
C6—C5—H5	119.3	H26C—C26'—H26D	107.7
C7—C6—C5	122.4 (3)	In1—Cl1—O2	91.52 (5)
C7—C6—H6	118.8	C17—N1—C1	112.7 (2)
C5—C6—H6	118.8	C17—N1—C9	111.1 (2)
C6—C7—C8	116.7 (3)	C1—N1—C9	111.5 (2)
C6—C7—H7	121.7	C17—N1—In1	106.19 (14)
C8—C7—H7	121.7	C1—N1—In1	106.27 (15)
N3—C8—C7	133.1 (3)	C9—N1—In1	108.81 (15)
N3—C8—C3	106.0 (2)	C2—N2—C3	106.5 (2)
C7—C8—C3	120.9 (3)	C2—N2—In1	117.06 (17)
N1—C9—C10	113.3 (2)	C3—N2—In1	136.28 (17)
N1—C9—H9A	108.9	C2—N3—C8	107.2 (2)
C10—C9—H9A	108.9	C2—N3—O1	122.7 (4)
N1—C9—H9B	108.9	C8—N3—O1	129.6 (4)
C10—C9—H9B	108.9	C2—N3—H3	126.4
H9A—C9—H9B	107.7	C8—N3—H3	126.4
N4—C10—N5	112.2 (2)	C10—N4—C11	106.1 (2)
N4—C10—C9	125.7 (2)	C10—N4—In1	114.55 (17)
N5—C10—C9	121.9 (2)	C11—N4—In1	138.28 (17)
C12—C11—N4	131.1 (3)	C10—N5—C16	107.8 (2)
C12—C11—C16	120.7 (3)	C10—N5—H5A	126.1
N4—C11—C16	108.1 (2)	C16—N5—H5A	126.1
C13—C12—C11	117.1 (3)	C18—N6—C19	106.4 (2)
C13—C12—H12	121.4	C18—N6—In1	115.33 (17)
C11—C12—H12	121.4	C19—N6—In1	138.08 (18)
C12—C13—C14	121.5 (3)	C18—N7—C24	107.8 (2)
C12—C13—H13	119.3	C18—N7—H7A	126.1
C14—C13—H13	119.3	C24—N7—H7A	126.1
C15—C14—C13	122.3 (3)	O3—O2—Cl3	102.18 (10)
C15—C14—H14	118.8	O3—O2—Cl1	108.16 (10)
C13—C14—H14	118.8	Cl3—O2—Cl1	90.17 (7)
C14—C15—C16	116.4 (3)	O3—O2—H2A	110 (3)
C14—C15—H15	121.8	Cl1—O2—H2A	71 (3)
C16—C15—H15	121.8	O3—O2—H2B	110 (3)
N5—C16—C15	132.4 (3)	Cl3—O2—H2B	128 (3)
N5—C16—C11	105.7 (2)	H2A—O2—H2B	109 (3)
C15—C16—C11	121.9 (3)	O2—O3—H3B	103 (3)
N1—C17—C18	108.9 (2)	H3A—O3—H3B	108 (3)
N1—C17—H17A	109.9	C26—O1—N3	108.6 (8)
C18—C17—H17A	109.9	C26—O1—H1	109.4
N1—C17—H17B	109.9	N3—O1—H1	141.9
C18—C17—H17B	109.9	C26—O1—H1'	106.6
H17A—C17—H17B	108.3	N3—O1—H1'	139.3
N6—C18—N7	111.9 (2)	C26'—O1'—H3	115.6
N6—C18—C17	123.3 (2)	C26'—O1'—H1	113.8
N7—C18—C17	124.8 (2)	H3—O1'—H1	116.6
C20—C19—N6	131.2 (3)	C26'—O1'—H1'	109.2
C20—C19—C24	120.8 (3)	H3—O1'—H1'	121.1
N6—C19—C24	108.0 (2)
N1—C1—C2—N2	32.2 (3)	C4—C3—N2—In1	1.4 (5)
N1—C1—C2—N3	−147.5 (3)	C8—C3—N2—In1	−175.54 (19)
N2—C3—C4—C5	−177.2 (3)	N4—In1—N2—C2	−92.1 (2)
C8—C3—C4—C5	−0.6 (4)	N6—In1—N2—C2	−16.7 (3)
C3—C4—C5—C6	−0.4 (5)	Cl1—In1—N2—C2	170.69 (18)
C4—C5—C6—C7	0.8 (6)	N1—In1—N2—C2	−15.16 (18)
C5—C6—C7—C8	−0.1 (6)	Cl2—In1—N2—C2	74.28 (19)
C6—C7—C8—N3	176.6 (3)	N4—In1—N2—C3	82.8 (3)
C6—C7—C8—C3	−1.0 (5)	N6—In1—N2—C3	158.2 (2)
C4—C3—C8—N3	−176.8 (3)	Cl1—In1—N2—C3	−14.4 (3)
N2—C3—C8—N3	0.5 (3)	N1—In1—N2—C3	159.8 (3)
C4—C3—C8—C7	1.4 (4)	Cl2—In1—N2—C3	−110.8 (2)
N2—C3—C8—C7	178.7 (3)	N2—C2—N3—C8	0.4 (3)
N1—C9—C10—N4	13.9 (4)	C1—C2—N3—C8	−179.8 (3)
N1—C9—C10—N5	−169.9 (2)	N2—C2—N3—O1	−171.9 (4)
N4—C11—C12—C13	177.5 (3)	C1—C2—N3—O1	7.9 (5)
C16—C11—C12—C13	1.3 (4)	C7—C8—N3—C2	−178.4 (3)
C11—C12—C13—C14	0.1 (4)	C3—C8—N3—C2	−0.5 (3)
C12—C13—C14—C15	−0.9 (5)	C7—C8—N3—O1	−6.8 (6)
C13—C14—C15—C16	0.3 (5)	C3—C8—N3—O1	171.0 (4)
C14—C15—C16—N5	−176.8 (3)	N5—C10—N4—C11	−1.7 (3)
C14—C15—C16—C11	1.2 (4)	C9—C10—N4—C11	174.7 (2)
C12—C11—C16—N5	176.5 (2)	N5—C10—N4—In1	168.72 (17)
N4—C11—C16—N5	−0.5 (3)	C9—C10—N4—In1	−14.8 (3)
C12—C11—C16—C15	−2.0 (4)	C12—C11—N4—C10	−175.2 (3)
N4—C11—C16—C15	−179.0 (2)	C16—C11—N4—C10	1.4 (3)
N1—C17—C18—N6	−27.6 (4)	C12—C11—N4—In1	17.9 (4)
N1—C17—C18—N7	155.0 (3)	C16—C11—N4—In1	−165.52 (19)
N6—C19—C20—C21	−177.2 (3)	N2—In1—N4—C10	80.35 (18)
C24—C19—C20—C21	0.9 (4)	N6—In1—N4—C10	−65.52 (18)
C19—C20—C21—C22	−0.4 (5)	Cl1—In1—N4—C10	−170.61 (17)
C20—C21—C22—C23	−0.6 (5)	N1—In1—N4—C10	7.55 (17)
C21—C22—C23—C24	1.2 (5)	Cl2—In1—N4—C10	12.4 (4)
C22—C23—C24—N7	177.5 (3)	N2—In1—N4—C11	−113.5 (3)
C22—C23—C24—C19	−0.7 (4)	N6—In1—N4—C11	100.6 (3)
C20—C19—C24—N7	−179.0 (3)	Cl1—In1—N4—C11	−4.5 (3)
N6—C19—C24—N7	−0.4 (3)	N1—In1—N4—C11	173.7 (3)
C20—C19—C24—C23	−0.3 (4)	Cl2—In1—N4—C11	178.55 (17)
N6—C19—C24—C23	178.2 (3)	N4—C10—N5—C16	1.4 (3)
N2—In1—Cl1—O2	−82.46 (8)	C9—C10—N5—C16	−175.2 (2)
N4—In1—Cl1—O2	−170.10 (7)	C15—C16—N5—C10	177.8 (3)
N6—In1—Cl1—O2	101.98 (8)	C11—C16—N5—C10	−0.5 (3)
Cl2—In1—Cl1—O2	9.13 (5)	N7—C18—N6—C19	0.1 (3)
C18—C17—N1—C1	153.9 (2)	C17—C18—N6—C19	−177.7 (2)
C18—C17—N1—C9	−80.2 (3)	N7—C18—N6—In1	176.14 (17)
C18—C17—N1—In1	38.0 (2)	C17—C18—N6—In1	−1.6 (3)
C2—C1—N1—C17	−155.8 (2)	C20—C19—N6—C18	178.5 (3)
C2—C1—N1—C9	78.6 (3)	C24—C19—N6—C18	0.2 (3)
C2—C1—N1—In1	−39.9 (2)	C20—C19—N6—In1	3.9 (5)
C10—C9—N1—C17	111.3 (2)	C24—C19—N6—In1	−174.4 (2)
C10—C9—N1—C1	−122.2 (2)	N2—In1—N6—C18	19.4 (3)
C10—C9—N1—In1	−5.3 (3)	N4—In1—N6—C18	94.52 (19)
N2—In1—N1—C17	150.47 (17)	Cl1—In1—N6—C18	−167.88 (18)
N4—In1—N1—C17	−120.38 (16)	N1—In1—N6—C18	17.80 (18)
N6—In1—N1—C17	−30.48 (15)	Cl2—In1—N6—C18	−71.11 (19)
Cl2—In1—N1—C17	60.86 (15)	N2—In1—N6—C19	−166.3 (2)
N2—In1—N1—C1	30.28 (16)	N4—In1—N6—C19	−91.1 (3)
N4—In1—N1—C1	119.44 (16)	Cl1—In1—N6—C19	6.5 (3)
N6—In1—N1—C1	−150.67 (17)	N1—In1—N6—C19	−167.8 (3)
Cl2—In1—N1—C1	−59.33 (15)	Cl2—In1—N6—C19	103.2 (3)
N2—In1—N1—C9	−89.91 (17)	N6—C18—N7—C24	−0.4 (3)
N4—In1—N1—C9	−0.75 (16)	C17—C18—N7—C24	177.3 (3)
N6—In1—N1—C9	89.14 (17)	C23—C24—N7—C18	−177.9 (3)
Cl2—In1—N1—C9	−179.52 (16)	C19—C24—N7—C18	0.5 (3)
N3—C2—N2—C3	−0.1 (3)	In1—Cl1—O2—O3	86.39 (9)
C1—C2—N2—C3	−179.9 (2)	In1—Cl1—O2—Cl3	−170.73 (6)
N3—C2—N2—In1	176.25 (17)	C25—C26—O1—N3	89.1 (15)
C1—C2—N2—In1	−3.6 (3)	C2—N3—O1—C26	70.9 (9)
C4—C3—N2—C2	176.7 (3)	C8—N3—O1—C26	−99.5 (8)
C8—C3—N2—C2	−0.3 (3)	C25'—C26'—O1'—H3	−107.0

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···Cl3i	0.97	2.70	3.655 (3)	168
C1—H1A···Cl3ii	0.97	2.74	3.558 (3)	142
N7—H7A···O3ii	0.86	2.01	2.826 (4)	158
N5—H5A···O2i	0.86	1.99	2.818 (4)	161
O3—H3B···Cl3iii	0.83 (2)	2.35 (2)	3.144 (3)	161 (4)
O3—H3A···O2	0.82 (2)	2.05 (2)	2.861 (4)	166 (4)
N3—H3···O1	0.86	1.90	2.745 (12)	169
N3—H3···O1'	0.86	1.89	2.718 (12)	160
O2—H2B···Cl2	0.83 (2)	2.41 (2)	3.171 (3)	154 (3)
O2—H2A···Cl3	0.82 (2)	2.34 (2)	3.108 (3)	155 (3)
O1—H1···Cl3iv	0.82	2.32	3.127 (11)	167
O1'—H1'···Cl3iv	0.82	2.49	3.178 (11)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯Cl3i	0.97	2.70	3.655 (3)	168
C1—H1A⋯Cl3ii	0.97	2.74	3.558 (3)	142
N7—H7A⋯O3ii	0.86	2.01	2.826 (4)	158
N5—H5A⋯O2i	0.86	1.99	2.818 (4)	161
O3—H3B⋯Cl3iii	0.83 (2)	2.35 (2)	3.144 (3)	161 (4)
O3—H3A⋯O2	0.82 (2)	2.05 (2)	2.861 (4)	166 (4)
N3—H3⋯O1	0.86	1.90	2.745 (12)	169
N3—H3⋯O1′	0.86	1.89	2.718 (12)	160
O2—H2B⋯Cl2	0.83 (2)	2.41 (2)	3.171 (3)	154 (3)
O2—H2A⋯Cl3	0.82 (2)	2.34 (2)	3.108 (3)	155 (3)
O1—H1⋯Cl3iv	0.82	2.32	3.127 (11)	167
O1′—H1′⋯Cl3iv	0.82	2.49	3.178 (11)	143

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .