Tetra­kis(μ-2-phen­oxy­propionato)-κ3O,O′:O′;κ3O:O,O′;κ4O:O′-bis­[(1,10-phenanthroline-κ2N,N′)(2-phen­oxy­propionato-κ2O,O′)holmium(III)]

Shen, J.-B.; Liu, J.-L.; Zhao, G.-L.

doi:10.1107/S160053681103738X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1401

https://doi.org/10.1107/S160053681103738X

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Tetrakis(μ-2-phenoxypropionato)-κ³O,O′:O′;κ³O:O,O′;κ⁴O:O′-bis[(1,10-phenanthroline-κ²N,N′)(2-phenoxypropionato-κ²O,O′)holmium(III)]

Jin-Bei Shen,^a Jia-Lu Liu ^a and Guo-Liang Zhao ^a,^b ^*

^aCollege of Chemistry and Life Sciences, Zhejiang Normal University, Jinhua 321004, Zhejiang, People's Republic of China, and ^bZhejiang Normal University Xingzhi College, Jinhua, Zhejiang 321004, People's Republic of China
^*Correspondence e-mail: sky53@zjnu.cn

(Received 9 August 2011; accepted 14 September 2011; online 20 September 2011)

The title compound, [Ho₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂], lies about a centre of symmetry and is comprised of six 2-phenoxypropionate (POPA) anions and two 1,10-phenanthroline (phen) ligands. The two Ho^III ions are linked by four POPA groups utilizing both bi- and tridentate bridging modes to form an inversion-symmetric dimer. Each Ho^III ion is nine-coordinate, with a chelating 1,10-phenanthroline molecule, one bidentate chelating carboxylate group, two bidentate bridging carboxylate groups and two tridentate bridging carboxylate groups in a distorted mono-capped square antiprism geometry. There are weak π–π aromatic interactions between the phen groups and aromatic rings of the POPA ligands [centroid–centroid distance = 3.829 (1) Å].

Related literature

For phenoxyalkanoic acids, see: Markus & Buser (1997 ). For holmium complexes, see: Hu et al. (2006 ); Zhao et al. (2010 ). For isotypic complexes, see: Shen et al. (2011a ,b ,c ,d ).

Experimental

Crystal data

[Ho₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]
M_r = 1681.24
Monoclinic, P 2₁ /c
a = 11.4657 (2) Å
b = 25.7960 (3) Å
c = 13.8366 (2) Å
β = 120.687 (1)°
V = 3519.37 (9) Å³
Z = 2
Mo Kα radiation
μ = 2.31 mm⁻¹
T = 296 K
0.25 × 0.16 × 0.06 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.656, T_max = 0.877
24604 measured reflections
6189 independent reflections
4266 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.062
S = 1.00
6189 reflections
464 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock global. DOI: https://doi.org/10.1107/S160053681103738X/pk2341sup1.cif

checkCIF report

Comment top

The group of phenoxyalkanoic acids includes a considerable number of important herbicides. The desired biological activity is largely dependent on the length of the carbon chain of the alkanoic acid, the nature of the phenoxy group, and the position of its attachment to the carbon chain (Markus & Buser, 1997). The fascinating structures of 2-phenoxypropionic acid complexes coupled with their special functionality catch our interests. Recently, we have reported our partial research results (Shen et al., 2011a,b,c,d). Here we describe a new Ho^III complex.

The structure of the complex is shown in Fig. 1 and the coordination environment of Ho^III is shown in Fig. 2. The dimeric title compound is centrosymmetric and is comprised of six L and two phen ligands. The two Ho^III ions are linked together by four L groups by bi- and tridentate bridging modes to form a dimeric unit with crystallographic inversion symmetry. The distance between two Ho^III ions is 3.9769 (4) Å, which is similar to analogous complexes (Hu et al., 2006; Zhao et al., 2010). Each Ho^III ion is coordinated to nine atoms, of which five are oxygen atoms from bridging carboxylates, two are oxygen atoms from the bidentate chelating carboxylate groups, and two are nitrogen atoms from a 1,10-phenanthroline molecule. The analysis of structural features indicates that the central Ho^III ion adopts a distorted mono-capped square antiprism geometry (Fig. 2). The Ho—O distances are all within the range 2.312 (3)–2.618 (3) Å, and the Ho—N distances are 2.500 (3) and 2.594 (3) Å. There are weak π–π aromatic interactions from phen molecules and aromatic rings of the L ligands.

Related literature top

For phenoxyalkanoic acids, see: Markus & Buser (1997). For holmium complexes, see: Hu et al. (2006); Zhao et al. (2010). For isotypic complexes, see: Shen et al. (2011a,b,c,d).

Experimental top

Reagents and solvents were of commercially available quality and were used without further purification. 2-phenoxypropionic acid (1.5 mmol), Ho(NO₃)₃.6H₂O (0.5 mmol) and 1,10-phenanthroline (0.5 mmol) were dissolved in 20 ml ethanol, then 10 ml water was added. The mixed solution was stirred for 12 h at room temperature. Solid deposits were removed by filtration, and the colourless solution allowed to slowly evaporate in air. Colourless crystals were obtained after several days.

Structure description top

For phenoxyalkanoic acids, see: Markus & Buser (1997). For holmium complexes, see: Hu et al. (2006); Zhao et al. (2010). For isotypic complexes, see: Shen et al. (2011a,b,c,d).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The coordination environment of the Ho^III.

Tetrakis(µ-2-phenoxypropionato)-κ³O,O':O'; κ³O:O,O';κ⁴O:O'-bis[(1,10- phenanthroline-κ²N,N')(2-phenoxypropionato- κ²O,O')holmium(III)] top

Crystal data top

[Ho₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]	F(000) = 1688
M_r = 1681.24	D_x = 1.587 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4156 reflections
a = 11.4657 (2) Å	θ = 1.6–25.0°
b = 25.7960 (3) Å	µ = 2.31 mm⁻¹
c = 13.8366 (2) Å	T = 296 K
β = 120.687 (1)°	Block, colourless
V = 3519.37 (9) Å³	0.25 × 0.16 × 0.06 mm
Z = 2

Data collection top

Bruker APEXII area-detector diffractometer	6189 independent reflections
Radiation source: fine-focus sealed tube	4266 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→10
T_min = 0.656, T_max = 0.877	k = −30→30
24604 measured reflections	l = −16→16

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0194P)²] where P = (F_o² + 2F_c²)/3
6189 reflections	(Δ/σ)_max = 0.001
464 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Ho₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]	V = 3519.37 (9) Å³
M_r = 1681.24	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.4657 (2) Å	µ = 2.31 mm⁻¹
b = 25.7960 (3) Å	T = 296 K
c = 13.8366 (2) Å	0.25 × 0.16 × 0.06 mm
β = 120.687 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	6189 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4266 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.877	R_int = 0.053
24604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.062	H-atom parameters constrained
S = 1.00	Δρ_max = 0.67 e Å⁻³
6189 reflections	Δρ_min = −0.55 e Å⁻³
464 parameters

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	U_iso*/U_eq
Ho1	0.453322 (18)	−0.002635 (6)	0.840539 (15)	0.02616 (7)
O1	0.3839 (3)	0.03107 (9)	0.9827 (2)	0.0317 (7)
O2	0.2468 (3)	0.04173 (9)	0.8017 (2)	0.0334 (7)
O3	0.0920 (3)	0.11048 (9)	0.8413 (2)	0.0406 (8)
O4	0.3347 (3)	−0.06690 (9)	0.8774 (2)	0.0315 (7)
O5	0.5809 (3)	0.06950 (9)	0.9358 (2)	0.0385 (8)
O6	0.1723 (3)	−0.15132 (11)	0.8456 (3)	0.0537 (9)
O7	0.5312 (3)	−0.08474 (9)	0.8029 (2)	0.0393 (8)
O8	0.6179 (3)	−0.01225 (9)	0.7835 (3)	0.0427 (8)
O9	0.5943 (3)	−0.13350 (10)	0.6562 (3)	0.0516 (9)
N1	0.3815 (3)	0.06779 (11)	0.6866 (3)	0.0317 (8)
N2	0.2831 (3)	−0.03033 (11)	0.6449 (3)	0.0303 (8)
C1	0.2748 (4)	0.04761 (13)	0.9009 (4)	0.0293 (10)
C2	0.1741 (4)	0.07333 (14)	0.9257 (4)	0.0348 (11)
H2	0.2229	0.0904	0.9991	0.052*
C3	0.0773 (5)	0.03325 (16)	0.9260 (4)	0.0511 (13)
H3A	0.0131	0.0500	0.9406	0.077*
H3B	0.1277	0.0080	0.9835	0.077*
H3C	0.0300	0.0164	0.8542	0.077*
C4	0.1569 (5)	0.15377 (15)	0.8342 (4)	0.0401 (12)
C5	0.2863 (5)	0.16791 (17)	0.9097 (5)	0.076 (2)
H5	0.3398	0.1469	0.9715	0.091*
C6	0.3385 (7)	0.2135 (2)	0.8946 (6)	0.102 (2)
H6	0.4262	0.2234	0.9481	0.123*
C7	0.2635 (7)	0.24415 (19)	0.8027 (6)	0.088 (2)
H7	0.3004	0.2742	0.7919	0.105*
C8	0.1341 (7)	0.22997 (19)	0.7274 (5)	0.0779 (19)
H8	0.0814	0.2510	0.6654	0.094*
C9	0.0793 (5)	0.18452 (17)	0.7415 (5)	0.0618 (15)
H9	−0.0090	0.1749	0.6888	0.074*
C10	0.3458 (4)	−0.08535 (14)	0.9658 (4)	0.0313 (11)
C11	0.2612 (5)	−0.13343 (15)	0.9561 (4)	0.0384 (12)
H11	0.3240	−0.1616	0.9984	0.058*
C12	0.1759 (5)	−0.12281 (17)	1.0082 (4)	0.0574 (14)
H12A	0.1252	−0.1533	1.0032	0.086*
H12B	0.1145	−0.0948	0.9689	0.086*
H12C	0.2337	−0.1135	1.0857	0.086*
C13	0.2213 (6)	−0.18197 (14)	0.7927 (4)	0.0466 (13)
C14	0.3536 (6)	−0.18429 (15)	0.8191 (4)	0.0537 (14)
H14	0.4204	−0.1658	0.8799	0.064*
C15	0.3859 (7)	−0.21419 (19)	0.7548 (6)	0.082 (2)
H15	0.4755	−0.2156	0.7718	0.098*
C16	0.2897 (10)	−0.2419 (2)	0.6662 (6)	0.100 (3)
H16	0.3138	−0.2624	0.6238	0.121*
C17	0.1569 (9)	−0.2397 (2)	0.6396 (5)	0.094 (2)
H17	0.0907	−0.2583	0.5786	0.113*
C18	0.1218 (6)	−0.20985 (16)	0.7032 (5)	0.0650 (16)
H18	0.0323	−0.2084	0.6862	0.078*
C19	0.6011 (5)	−0.06062 (16)	0.7727 (4)	0.0369 (11)
C20	0.6725 (5)	−0.09027 (16)	0.7207 (4)	0.0440 (12)
H20	0.6894	−0.0669	0.6733	0.066*
C21	0.8065 (5)	−0.11263 (18)	0.8140 (4)	0.0668 (16)
H21A	0.8502	−0.1313	0.7812	0.100*
H21B	0.7891	−0.1357	0.8597	0.100*
H21C	0.8642	−0.0849	0.8596	0.100*
C22	0.4850 (5)	−0.12432 (17)	0.5496 (4)	0.0447 (12)
C23	0.4492 (5)	−0.07704 (18)	0.4982 (4)	0.0508 (13)
H23	0.4958	−0.0473	0.5362	0.061*
C24	0.3431 (6)	−0.0744 (2)	0.3893 (5)	0.0618 (15)
H24	0.3197	−0.0424	0.3532	0.074*
C25	0.2704 (5)	−0.1175 (2)	0.3321 (5)	0.0665 (16)
H25	0.1985	−0.1151	0.2585	0.080*
C26	0.3070 (6)	−0.1646 (2)	0.3868 (5)	0.0679 (17)
H26	0.2585	−0.1942	0.3498	0.081*
C27	0.4133 (5)	−0.16837 (17)	0.4946 (5)	0.0557 (14)
H27	0.4372	−0.2003	0.5306	0.067*
C28	0.4299 (5)	0.11540 (14)	0.7059 (4)	0.0415 (12)
H28	0.5047	0.1229	0.7760	0.050*
C29	0.3747 (5)	0.15526 (15)	0.6267 (4)	0.0509 (14)
H29	0.4124	0.1883	0.6440	0.061*
C30	0.2652 (5)	0.14510 (15)	0.5242 (4)	0.0486 (13)
H30	0.2272	0.1712	0.4705	0.058*
C31	0.0953 (5)	0.08180 (17)	0.3942 (4)	0.0459 (13)
H31	0.0526	0.1072	0.3394	0.055*
C32	0.0474 (5)	0.03298 (17)	0.3718 (4)	0.0419 (12)
H32	−0.0276	0.0253	0.3019	0.050*
C33	0.0655 (4)	−0.05879 (16)	0.4337 (4)	0.0401 (12)
H33	−0.0076	−0.0686	0.3644	0.048*
C34	0.1309 (5)	−0.09425 (16)	0.5172 (4)	0.0425 (12)
H34	0.1041	−0.1288	0.5047	0.051*
C35	0.2385 (4)	−0.07875 (14)	0.6218 (4)	0.0372 (11)
H35	0.2808	−0.1036	0.6779	0.045*
C36	0.2098 (5)	0.09545 (15)	0.4997 (4)	0.0365 (11)
C37	0.2728 (4)	0.05725 (14)	0.5842 (4)	0.0295 (10)
C38	0.1101 (4)	−0.00725 (15)	0.4539 (3)	0.0359 (10)
C39	0.2193 (4)	0.00509 (14)	0.5603 (3)	0.0292 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ho1	0.02474 (12)	0.02897 (10)	0.02041 (12)	−0.00023 (10)	0.00836 (9)	−0.00045 (9)
O1	0.0256 (19)	0.0364 (15)	0.0211 (18)	0.0048 (13)	0.0032 (16)	0.0027 (13)
O2	0.0289 (19)	0.0441 (16)	0.0230 (19)	0.0058 (13)	0.0103 (17)	0.0018 (13)
O3	0.0237 (18)	0.0361 (15)	0.049 (2)	0.0042 (13)	0.0094 (17)	0.0010 (14)
O4	0.0348 (19)	0.0339 (14)	0.0211 (18)	−0.0086 (13)	0.0108 (16)	−0.0037 (13)
O5	0.045 (2)	0.0368 (15)	0.027 (2)	−0.0107 (14)	0.0129 (18)	−0.0025 (14)
O6	0.045 (2)	0.0491 (18)	0.052 (3)	−0.0090 (16)	0.014 (2)	−0.0099 (16)
O7	0.033 (2)	0.0384 (15)	0.044 (2)	0.0008 (14)	0.0175 (18)	−0.0031 (14)
O8	0.048 (2)	0.0388 (17)	0.050 (2)	−0.0029 (14)	0.0315 (19)	−0.0047 (14)
O9	0.061 (2)	0.0438 (17)	0.040 (2)	0.0085 (16)	0.018 (2)	−0.0067 (16)
N1	0.032 (2)	0.0333 (18)	0.026 (2)	−0.0017 (16)	0.012 (2)	0.0012 (16)
N2	0.028 (2)	0.0331 (17)	0.021 (2)	−0.0006 (16)	0.0064 (19)	−0.0003 (16)
C1	0.027 (3)	0.026 (2)	0.032 (3)	−0.0072 (19)	0.013 (3)	−0.002 (2)
C2	0.031 (3)	0.039 (2)	0.029 (3)	0.004 (2)	0.012 (2)	0.000 (2)
C3	0.048 (3)	0.062 (3)	0.059 (4)	−0.003 (2)	0.039 (3)	0.000 (3)
C4	0.030 (3)	0.035 (2)	0.045 (4)	0.006 (2)	0.012 (3)	−0.002 (2)
C5	0.043 (4)	0.044 (3)	0.084 (5)	−0.010 (3)	−0.010 (4)	0.016 (3)
C6	0.071 (5)	0.065 (4)	0.111 (6)	−0.023 (3)	0.002 (5)	0.017 (4)
C7	0.077 (5)	0.047 (3)	0.115 (6)	−0.010 (3)	0.032 (5)	0.016 (4)
C8	0.087 (5)	0.055 (3)	0.067 (5)	0.004 (3)	0.021 (4)	0.017 (3)
C9	0.052 (4)	0.048 (3)	0.060 (4)	0.004 (3)	0.011 (3)	0.002 (3)
C10	0.031 (3)	0.029 (2)	0.037 (3)	0.0013 (19)	0.020 (3)	−0.001 (2)
C11	0.040 (3)	0.040 (2)	0.030 (3)	−0.015 (2)	0.013 (3)	−0.007 (2)
C12	0.052 (4)	0.072 (3)	0.056 (4)	−0.019 (3)	0.033 (3)	−0.010 (3)
C13	0.070 (4)	0.023 (2)	0.047 (4)	−0.002 (2)	0.030 (3)	−0.005 (2)
C14	0.060 (4)	0.037 (3)	0.062 (4)	−0.002 (3)	0.029 (4)	−0.005 (2)
C15	0.110 (6)	0.048 (3)	0.116 (6)	0.007 (3)	0.079 (5)	0.004 (3)
C16	0.177 (9)	0.065 (4)	0.086 (6)	0.007 (5)	0.086 (7)	−0.012 (4)
C17	0.135 (7)	0.058 (4)	0.057 (5)	−0.005 (5)	0.026 (5)	−0.022 (3)
C18	0.073 (4)	0.036 (3)	0.059 (4)	−0.002 (3)	0.014 (4)	−0.001 (3)
C19	0.030 (3)	0.048 (3)	0.024 (3)	0.002 (2)	0.007 (2)	−0.005 (2)
C20	0.039 (3)	0.055 (3)	0.036 (3)	0.000 (2)	0.018 (3)	−0.010 (2)
C21	0.045 (4)	0.096 (4)	0.051 (4)	0.027 (3)	0.018 (3)	−0.012 (3)
C22	0.048 (4)	0.054 (3)	0.037 (3)	0.008 (3)	0.025 (3)	−0.005 (3)
C23	0.050 (4)	0.056 (3)	0.042 (4)	−0.001 (3)	0.021 (3)	−0.004 (3)
C24	0.054 (4)	0.082 (4)	0.053 (4)	0.010 (3)	0.030 (4)	0.019 (3)
C25	0.041 (4)	0.118 (5)	0.033 (4)	−0.003 (4)	0.014 (3)	−0.010 (4)
C26	0.059 (4)	0.075 (4)	0.068 (5)	−0.014 (3)	0.031 (4)	−0.026 (3)
C27	0.053 (4)	0.049 (3)	0.059 (4)	0.001 (3)	0.024 (3)	−0.013 (3)
C28	0.042 (3)	0.040 (2)	0.035 (3)	−0.002 (2)	0.014 (3)	0.001 (2)
C29	0.059 (4)	0.035 (2)	0.049 (4)	−0.004 (2)	0.020 (3)	0.007 (2)
C30	0.052 (4)	0.040 (3)	0.050 (4)	0.009 (2)	0.023 (3)	0.018 (2)
C31	0.047 (3)	0.058 (3)	0.032 (3)	0.015 (3)	0.020 (3)	0.012 (2)
C32	0.034 (3)	0.063 (3)	0.020 (3)	0.008 (2)	0.008 (3)	−0.001 (2)
C33	0.033 (3)	0.058 (3)	0.021 (3)	−0.004 (2)	0.007 (3)	−0.012 (2)
C34	0.045 (3)	0.045 (2)	0.032 (3)	−0.013 (2)	0.016 (3)	−0.010 (2)
C35	0.038 (3)	0.039 (2)	0.030 (3)	−0.001 (2)	0.014 (3)	−0.001 (2)
C36	0.037 (3)	0.045 (2)	0.027 (3)	0.010 (2)	0.016 (3)	0.007 (2)
C37	0.024 (3)	0.040 (2)	0.026 (3)	0.008 (2)	0.014 (2)	0.001 (2)
C38	0.028 (3)	0.056 (3)	0.018 (3)	−0.001 (2)	0.008 (2)	−0.002 (2)
C39	0.028 (2)	0.039 (2)	0.021 (2)	−0.001 (2)	0.013 (2)	−0.006 (2)

Geometric parameters (Å, º) top

Ho1—O1ⁱ	2.312 (3)	C12—H12B	0.9600
Ho1—O5	2.318 (3)	C12—H12C	0.9600
Ho1—O4	2.359 (3)	C13—C14	1.368 (6)
Ho1—O8	2.401 (3)	C13—C18	1.382 (6)
Ho1—O2	2.431 (3)	C14—C15	1.364 (7)
Ho1—O7	2.455 (2)	C14—H14	0.9300
Ho1—N2	2.500 (3)	C15—C16	1.361 (8)
Ho1—N1	2.594 (3)	C15—H15	0.9300
Ho1—O1	2.618 (3)	C16—C17	1.373 (8)
Ho1—C19	2.759 (4)	C16—H16	0.9300
Ho1—C1	2.883 (4)	C17—C18	1.374 (8)
Ho1—Ho1ⁱ	3.9769 (4)	C17—H17	0.9300
O1—C1	1.258 (5)	C18—H18	0.9300
O1—Ho1ⁱ	2.312 (3)	C19—C20	1.541 (5)
O2—C1	1.249 (5)	C20—C21	1.528 (6)
O3—C4	1.373 (5)	C20—H20	0.9800
O3—C2	1.430 (4)	C21—H21A	0.9600
O4—C10	1.257 (5)	C21—H21B	0.9600
O5—C10ⁱ	1.249 (5)	C21—H21C	0.9600
O6—C13	1.377 (5)	C22—C23	1.365 (6)
O6—C11	1.414 (5)	C22—C27	1.381 (6)
O7—C19	1.243 (5)	C23—C24	1.372 (6)
O8—C19	1.260 (4)	C23—H23	0.9300
O9—C22	1.384 (5)	C24—C25	1.374 (6)
O9—C20	1.424 (5)	C24—H24	0.9300
N1—C28	1.318 (4)	C25—C26	1.377 (7)
N1—C37	1.354 (5)	C25—H25	0.9300
N2—C35	1.325 (4)	C26—C27	1.365 (6)
N2—C39	1.366 (5)	C26—H26	0.9300
C1—C2	1.515 (5)	C27—H27	0.9300
C2—C3	1.518 (5)	C28—C29	1.397 (5)
C2—H2	0.9800	C28—H28	0.9300
C3—H3A	0.9600	C29—C30	1.356 (6)
C3—H3B	0.9600	C29—H29	0.9300
C3—H3C	0.9600	C30—C36	1.392 (5)
C4—C5	1.358 (6)	C30—H30	0.9300
C4—C9	1.379 (6)	C31—C32	1.346 (5)
C5—C6	1.382 (6)	C31—C36	1.422 (6)
C5—H5	0.9300	C31—H31	0.9300
C6—C7	1.367 (7)	C32—C38	1.432 (5)
C6—H6	0.9300	C32—H32	0.9300
C7—C8	1.357 (7)	C33—C34	1.360 (5)
C7—H7	0.9300	C33—C38	1.401 (5)
C8—C9	1.391 (6)	C33—H33	0.9300
C8—H8	0.9300	C34—C35	1.398 (5)
C9—H9	0.9300	C34—H34	0.9300
C10—O5ⁱ	1.249 (5)	C35—H35	0.9300
C10—C11	1.538 (5)	C36—C37	1.413 (5)
C11—C12	1.507 (6)	C37—C39	1.445 (5)
C11—H11	0.9800	C38—C39	1.398 (5)
C12—H12A	0.9600

O1ⁱ—Ho1—O5	73.65 (9)	C6—C7—H7	120.6
O1ⁱ—Ho1—O4	77.96 (9)	C7—C8—C9	121.0 (5)
O5—Ho1—O4	135.01 (9)	C7—C8—H8	119.5
O1ⁱ—Ho1—O8	88.25 (10)	C9—C8—H8	119.5
O5—Ho1—O8	84.04 (9)	C4—C9—C8	119.5 (5)
O4—Ho1—O8	129.41 (8)	C4—C9—H9	120.2
O1ⁱ—Ho1—O2	123.55 (9)	C8—C9—H9	120.2
O5—Ho1—O2	90.48 (9)	O5ⁱ—C10—O4	127.9 (4)
O4—Ho1—O2	76.97 (9)	O5ⁱ—C10—C11	113.7 (4)
O8—Ho1—O2	144.74 (9)	O4—C10—C11	118.3 (4)
O1ⁱ—Ho1—O7	76.49 (9)	O6—C11—C12	106.9 (4)
O5—Ho1—O7	128.40 (10)	O6—C11—C10	115.6 (4)
O4—Ho1—O7	75.63 (9)	C12—C11—C10	110.3 (3)
O8—Ho1—O7	53.80 (9)	O6—C11—H11	107.9
O2—Ho1—O7	141.07 (9)	C12—C11—H11	107.9
O1ⁱ—Ho1—N2	144.81 (9)	C10—C11—H11	107.9
O5—Ho1—N2	139.68 (10)	C11—C12—H12A	109.5
O4—Ho1—N2	79.38 (10)	C11—C12—H12B	109.5
O8—Ho1—N2	85.69 (10)	H12A—C12—H12B	109.5
O2—Ho1—N2	76.18 (10)	C11—C12—H12C	109.5
O7—Ho1—N2	72.01 (10)	H12A—C12—H12C	109.5
O1ⁱ—Ho1—N1	146.90 (10)	H12B—C12—H12C	109.5
O5—Ho1—N1	75.43 (10)	C14—C13—O6	125.5 (4)
O4—Ho1—N1	133.91 (10)	C14—C13—C18	120.8 (5)
O8—Ho1—N1	77.03 (10)	O6—C13—C18	113.7 (5)
O2—Ho1—N1	67.89 (10)	C15—C14—C13	119.0 (5)
O7—Ho1—N1	115.29 (10)	C15—C14—H14	120.5
N2—Ho1—N1	64.27 (10)	C13—C14—H14	120.5
O1ⁱ—Ho1—O1	72.63 (10)	C16—C15—C14	121.3 (6)
O5—Ho1—O1	69.61 (9)	C16—C15—H15	119.3
O4—Ho1—O1	68.97 (8)	C14—C15—H15	119.3
O8—Ho1—O1	150.74 (9)	C15—C16—C17	119.8 (7)
O2—Ho1—O1	51.26 (9)	C15—C16—H16	120.1
O7—Ho1—O1	136.78 (9)	C17—C16—H16	120.1
N2—Ho1—O1	122.64 (10)	C16—C17—C18	120.0 (6)
N1—Ho1—O1	107.07 (9)	C16—C17—H17	120.0
O1ⁱ—Ho1—C19	83.31 (11)	C18—C17—H17	120.0
O5—Ho1—C19	108.06 (12)	C17—C18—C13	119.2 (6)
O4—Ho1—C19	102.38 (12)	C17—C18—H18	120.4
O8—Ho1—C19	27.15 (10)	C13—C18—H18	120.4
O2—Ho1—C19	151.44 (11)	O7—C19—O8	122.8 (4)
O7—Ho1—C19	26.78 (10)	O7—C19—C20	119.7 (4)
N2—Ho1—C19	75.67 (11)	O8—C19—C20	117.5 (4)
N1—Ho1—C19	95.34 (12)	O7—C19—Ho1	62.9 (2)
O1—Ho1—C19	155.57 (11)	O8—C19—Ho1	60.4 (2)
O1ⁱ—Ho1—C1	98.36 (12)	C20—C19—Ho1	173.1 (3)
O5—Ho1—C1	79.01 (10)	O9—C20—C21	105.9 (4)
O4—Ho1—C1	71.37 (9)	O9—C20—C19	111.5 (4)
O8—Ho1—C1	159.21 (9)	C21—C20—C19	109.7 (4)
O2—Ho1—C1	25.40 (10)	O9—C20—H20	109.9
O7—Ho1—C1	146.93 (10)	C21—C20—H20	109.9
N2—Ho1—C1	99.48 (12)	C19—C20—H20	109.9
N1—Ho1—C1	87.04 (11)	C20—C21—H21A	109.5
O1—Ho1—C1	25.86 (10)	C20—C21—H21B	109.5
C19—Ho1—C1	172.89 (12)	H21A—C21—H21B	109.5
O1ⁱ—Ho1—Ho1ⁱ	38.93 (6)	C20—C21—H21C	109.5
O5—Ho1—Ho1ⁱ	66.86 (7)	H21A—C21—H21C	109.5
O4—Ho1—Ho1ⁱ	69.05 (6)	H21B—C21—H21C	109.5
O8—Ho1—Ho1ⁱ	123.82 (7)	C23—C22—C27	120.8 (5)
O2—Ho1—Ho1ⁱ	84.79 (7)	C23—C22—O9	125.2 (4)
O7—Ho1—Ho1ⁱ	110.11 (7)	C27—C22—O9	114.0 (4)
N2—Ho1—Ho1ⁱ	146.12 (7)	C22—C23—C24	118.6 (5)
N1—Ho1—Ho1ⁱ	132.87 (7)	C22—C23—H23	120.7
O1—Ho1—Ho1ⁱ	33.70 (6)	C24—C23—H23	120.7
C19—Ho1—Ho1ⁱ	122.12 (9)	C23—C24—C25	121.9 (5)
C1—Ho1—Ho1ⁱ	59.47 (9)	C23—C24—H24	119.1
C1—O1—Ho1ⁱ	162.7 (3)	C25—C24—H24	119.1
C1—O1—Ho1	88.9 (2)	C24—C25—C26	118.2 (5)
Ho1ⁱ—O1—Ho1	107.37 (10)	C24—C25—H25	120.9
C1—O2—Ho1	98.0 (3)	C26—C25—H25	120.9
C4—O3—C2	116.6 (3)	C27—C26—C25	121.0 (5)
C10—O4—Ho1	133.9 (3)	C27—C26—H26	119.5
C10ⁱ—O5—Ho1	139.6 (3)	C25—C26—H26	119.5
C13—O6—C11	119.9 (4)	C26—C27—C22	119.4 (5)
C19—O7—Ho1	90.4 (2)	C26—C27—H27	120.3
C19—O8—Ho1	92.4 (3)	C22—C27—H27	120.3
C22—O9—C20	118.1 (3)	N1—C28—C29	123.5 (4)
C28—N1—C37	117.8 (3)	N1—C28—H28	118.3
C28—N1—Ho1	124.2 (3)	C29—C28—H28	118.3
C37—N1—Ho1	117.1 (2)	C30—C29—C28	119.0 (4)
C35—N2—C39	116.8 (4)	C30—C29—H29	120.5
C35—N2—Ho1	121.5 (3)	C28—C29—H29	120.5
C39—N2—Ho1	121.1 (2)	C29—C30—C36	119.7 (4)
O2—C1—O1	121.8 (4)	C29—C30—H30	120.1
O2—C1—C2	120.2 (4)	C36—C30—H30	120.1
O1—C1—C2	117.9 (4)	C32—C31—C36	121.5 (4)
O2—C1—Ho1	56.6 (2)	C32—C31—H31	119.2
O1—C1—Ho1	65.2 (2)	C36—C31—H31	119.2
C2—C1—Ho1	176.6 (3)	C31—C32—C38	121.0 (4)
O3—C2—C1	111.6 (3)	C31—C32—H32	119.5
O3—C2—C3	106.3 (3)	C38—C32—H32	119.5
C1—C2—C3	110.2 (3)	C34—C33—C38	118.8 (4)
O3—C2—H2	109.5	C34—C33—H33	120.6
C1—C2—H2	109.5	C38—C33—H33	120.6
C3—C2—H2	109.5	C33—C34—C35	120.0 (4)
C2—C3—H3A	109.5	C33—C34—H34	120.0
C2—C3—H3B	109.5	C35—C34—H34	120.0
H3A—C3—H3B	109.5	N2—C35—C34	123.2 (4)
C2—C3—H3C	109.5	N2—C35—H35	118.4
H3A—C3—H3C	109.5	C34—C35—H35	118.4
H3B—C3—H3C	109.5	C30—C36—C37	117.6 (4)
C5—C4—O3	125.7 (4)	C30—C36—C31	123.0 (4)
C5—C4—C9	119.6 (5)	C37—C36—C31	119.4 (4)
O3—C4—C9	114.7 (4)	N1—C37—C36	122.3 (4)
C4—C5—C6	120.0 (5)	N1—C37—C39	118.9 (3)
C4—C5—H5	120.0	C36—C37—C39	118.8 (4)
C6—C5—H5	120.0	C39—C38—C33	117.8 (4)
C7—C6—C5	121.2 (6)	C39—C38—C32	119.2 (4)
C7—C6—H6	119.4	C33—C38—C32	123.0 (4)
C5—C6—H6	119.4	N2—C39—C38	123.4 (4)
C8—C7—C6	118.7 (5)	N2—C39—C37	116.6 (4)
C8—C7—H7	120.6	C38—C39—C37	120.0 (4)

O1ⁱ—Ho1—O1—C1	−174.0 (3)	O4—Ho1—C1—O2	−98.9 (2)
O5—Ho1—O1—C1	107.5 (2)	O8—Ho1—C1—O2	79.4 (4)
O4—Ho1—O1—C1	−90.5 (2)	O7—Ho1—C1—O2	−95.1 (3)
O8—Ho1—O1—C1	134.6 (2)	N2—Ho1—C1—O2	−23.6 (2)
O2—Ho1—O1—C1	−0.6 (2)	N1—Ho1—C1—O2	39.7 (2)
O7—Ho1—O1—C1	−127.6 (2)	O1—Ho1—C1—O2	−179.0 (4)
N2—Ho1—O1—C1	−29.2 (2)	Ho1ⁱ—Ho1—C1—O2	−175.1 (2)
N1—Ho1—O1—C1	40.7 (2)	O1ⁱ—Ho1—C1—O1	5.8 (2)
C19—Ho1—O1—C1	−163.6 (3)	O5—Ho1—C1—O1	−65.6 (2)
Ho1ⁱ—Ho1—O1—C1	−174.0 (3)	O4—Ho1—C1—O1	80.1 (2)
O1ⁱ—Ho1—O1—Ho1ⁱ	0.0	O8—Ho1—C1—O1	−101.6 (4)
O5—Ho1—O1—Ho1ⁱ	−78.56 (11)	O2—Ho1—C1—O1	179.0 (4)
O4—Ho1—O1—Ho1ⁱ	83.47 (11)	O7—Ho1—C1—O1	83.9 (3)
O8—Ho1—O1—Ho1ⁱ	−51.4 (2)	N2—Ho1—C1—O1	155.4 (2)
O2—Ho1—O1—Ho1ⁱ	173.40 (14)	N1—Ho1—C1—O1	−141.3 (2)
O7—Ho1—O1—Ho1ⁱ	46.34 (16)	Ho1ⁱ—Ho1—C1—O1	3.89 (16)
N2—Ho1—O1—Ho1ⁱ	144.74 (10)	C4—O3—C2—C1	−66.7 (4)
N1—Ho1—O1—Ho1ⁱ	−145.30 (10)	C4—O3—C2—C3	173.1 (3)
C19—Ho1—O1—Ho1ⁱ	10.4 (3)	O2—C1—C2—O3	−30.2 (5)
C1—Ho1—O1—Ho1ⁱ	174.0 (3)	O1—C1—C2—O3	152.3 (3)
O1ⁱ—Ho1—O2—C1	8.1 (2)	O2—C1—C2—C3	87.8 (4)
O5—Ho1—O2—C1	−62.5 (2)	O1—C1—C2—C3	−89.8 (4)
O4—Ho1—O2—C1	73.9 (2)	C2—O3—C4—C5	−10.2 (6)
O8—Ho1—O2—C1	−142.8 (2)	C2—O3—C4—C9	170.4 (4)
O7—Ho1—O2—C1	120.1 (2)	O3—C4—C5—C6	−177.9 (5)
N2—Ho1—O2—C1	156.0 (2)	C9—C4—C5—C6	1.5 (9)
N1—Ho1—O2—C1	−136.5 (2)	C4—C5—C6—C7	−2.1 (10)
O1—Ho1—O2—C1	0.6 (2)	C5—C6—C7—C8	2.1 (11)
C19—Ho1—O2—C1	165.9 (3)	C6—C7—C8—C9	−1.5 (10)
Ho1ⁱ—Ho1—O2—C1	4.2 (2)	C5—C4—C9—C8	−0.9 (8)
O1ⁱ—Ho1—O4—C10	26.4 (3)	O3—C4—C9—C8	178.6 (4)
O5—Ho1—O4—C10	−25.2 (4)	C7—C8—C9—C4	0.9 (9)
O8—Ho1—O4—C10	104.0 (3)	Ho1—O4—C10—O5ⁱ	8.8 (7)
O2—Ho1—O4—C10	−102.6 (3)	Ho1—O4—C10—C11	−171.0 (2)
O7—Ho1—O4—C10	105.4 (3)	C13—O6—C11—C12	−155.4 (4)
N2—Ho1—O4—C10	179.3 (4)	C13—O6—C11—C10	81.5 (5)
N1—Ho1—O4—C10	−143.2 (3)	O5ⁱ—C10—C11—O6	177.4 (4)
O1—Ho1—O4—C10	−49.4 (3)	O4—C10—C11—O6	−2.8 (6)
C19—Ho1—O4—C10	106.7 (3)	O5ⁱ—C10—C11—C12	56.0 (5)
C1—Ho1—O4—C10	−76.8 (4)	O4—C10—C11—C12	−124.2 (4)
Ho1ⁱ—Ho1—O4—C10	−13.2 (3)	C11—O6—C13—C14	−22.5 (6)
O1ⁱ—Ho1—O5—C10ⁱ	−24.5 (4)	C11—O6—C13—C18	160.5 (4)
O4—Ho1—O5—C10ⁱ	28.6 (5)	O6—C13—C14—C15	−176.1 (4)
O8—Ho1—O5—C10ⁱ	−114.4 (4)	C18—C13—C14—C15	0.7 (7)
O2—Ho1—O5—C10ⁱ	100.5 (4)	C13—C14—C15—C16	−0.6 (8)
O7—Ho1—O5—C10ⁱ	−81.6 (4)	C14—C15—C16—C17	0.6 (10)
N2—Ho1—O5—C10ⁱ	169.5 (4)	C15—C16—C17—C18	−0.7 (11)
N1—Ho1—O5—C10ⁱ	167.5 (4)	C16—C17—C18—C13	0.7 (9)
O1—Ho1—O5—C10ⁱ	52.7 (4)	C14—C13—C18—C17	−0.8 (8)
C19—Ho1—O5—C10ⁱ	−101.6 (4)	O6—C13—C18—C17	176.4 (4)
C1—Ho1—O5—C10ⁱ	77.7 (4)	Ho1—O7—C19—O8	7.8 (4)
Ho1ⁱ—Ho1—O5—C10ⁱ	16.4 (4)	Ho1—O7—C19—C20	−172.7 (4)
O1ⁱ—Ho1—O7—C19	−102.1 (3)	Ho1—O8—C19—O7	−8.0 (4)
O5—Ho1—O7—C19	−46.2 (3)	Ho1—O8—C19—C20	172.5 (3)
O4—Ho1—O7—C19	177.1 (3)	O1ⁱ—Ho1—C19—O7	73.2 (2)
O8—Ho1—O7—C19	−4.3 (2)	O5—Ho1—C19—O7	143.5 (2)
O2—Ho1—O7—C19	130.5 (2)	O4—Ho1—C19—O7	−2.9 (3)
N2—Ho1—O7—C19	93.8 (3)	O8—Ho1—C19—O7	172.4 (4)
N1—Ho1—O7—C19	44.9 (3)	O2—Ho1—C19—O7	−88.4 (3)
O1—Ho1—O7—C19	−147.4 (2)	N2—Ho1—C19—O7	−78.4 (2)
C1—Ho1—O7—C19	173.3 (3)	N1—Ho1—C19—O7	−140.1 (2)
Ho1ⁱ—Ho1—O7—C19	−122.1 (2)	O1—Ho1—C19—O7	63.2 (4)
O1ⁱ—Ho1—O8—C19	78.7 (2)	Ho1ⁱ—Ho1—C19—O7	70.0 (3)
O5—Ho1—O8—C19	152.5 (3)	O1ⁱ—Ho1—C19—O8	−99.3 (2)
O4—Ho1—O8—C19	5.9 (3)	O5—Ho1—C19—O8	−28.9 (3)
O2—Ho1—O8—C19	−125.2 (2)	O4—Ho1—C19—O8	−175.4 (2)
O7—Ho1—O8—C19	4.2 (2)	O2—Ho1—C19—O8	99.2 (3)
N2—Ho1—O8—C19	−66.6 (2)	O7—Ho1—C19—O8	−172.4 (4)
N1—Ho1—O8—C19	−131.2 (3)	N2—Ho1—C19—O8	109.2 (3)
O1—Ho1—O8—C19	127.0 (3)	N1—Ho1—C19—O8	47.5 (2)
C1—Ho1—O8—C19	−172.1 (3)	O1—Ho1—C19—O8	−109.3 (3)
Ho1ⁱ—Ho1—O8—C19	95.5 (2)	Ho1ⁱ—Ho1—C19—O8	−102.5 (2)
O1ⁱ—Ho1—N1—C28	−22.1 (4)	C22—O9—C20—C21	−162.5 (4)
O5—Ho1—N1—C28	−0.7 (3)	C22—O9—C20—C19	78.2 (5)
O4—Ho1—N1—C28	139.1 (3)	O7—C19—C20—O9	33.8 (6)
O8—Ho1—N1—C28	−87.8 (3)	O8—C19—C20—O9	−146.8 (4)
O2—Ho1—N1—C28	95.9 (3)	O7—C19—C20—C21	−83.2 (5)
O7—Ho1—N1—C28	−126.6 (3)	O8—C19—C20—C21	96.3 (5)
N2—Ho1—N1—C28	−179.3 (4)	C20—O9—C22—C23	3.4 (6)
O1—Ho1—N1—C28	62.2 (3)	C20—O9—C22—C27	−178.5 (4)
C19—Ho1—N1—C28	−108.0 (3)	C27—C22—C23—C24	−2.0 (7)
C1—Ho1—N1—C28	78.7 (3)	O9—C22—C23—C24	176.0 (4)
Ho1ⁱ—Ho1—N1—C28	36.6 (4)	C22—C23—C24—C25	1.6 (8)
O1ⁱ—Ho1—N1—C37	168.8 (2)	C23—C24—C25—C26	−0.3 (8)
O5—Ho1—N1—C37	−169.8 (3)	C24—C25—C26—C27	−0.6 (8)
O4—Ho1—N1—C37	−30.0 (3)	C25—C26—C27—C22	0.2 (8)
O8—Ho1—N1—C37	103.0 (3)	C23—C22—C27—C26	1.2 (7)
O2—Ho1—N1—C37	−73.2 (3)	O9—C22—C27—C26	−177.0 (4)
O7—Ho1—N1—C37	64.2 (3)	C37—N1—C28—C29	0.2 (6)
N2—Ho1—N1—C37	11.6 (2)	Ho1—N1—C28—C29	−168.9 (3)
O1—Ho1—N1—C37	−107.0 (3)	N1—C28—C29—C30	0.2 (7)
C19—Ho1—N1—C37	82.9 (3)	C28—C29—C30—C36	0.1 (7)
C1—Ho1—N1—C37	−90.4 (3)	C36—C31—C32—C38	0.1 (7)
Ho1ⁱ—Ho1—N1—C37	−132.5 (2)	C38—C33—C34—C35	1.5 (7)
O1ⁱ—Ho1—N2—C35	18.3 (4)	C39—N2—C35—C34	−0.5 (6)
O5—Ho1—N2—C35	174.6 (3)	Ho1—N2—C35—C34	171.3 (3)
O4—Ho1—N2—C35	−32.4 (3)	C33—C34—C35—N2	−0.9 (7)
O8—Ho1—N2—C35	99.1 (3)	C29—C30—C36—C37	−0.8 (6)
O2—Ho1—N2—C35	−111.4 (3)	C29—C30—C36—C31	−179.9 (4)
O7—Ho1—N2—C35	45.8 (3)	C32—C31—C36—C30	177.5 (4)
N1—Ho1—N2—C35	176.7 (3)	C32—C31—C36—C37	−1.6 (6)
O1—Ho1—N2—C35	−88.8 (3)	C28—N1—C37—C36	−1.0 (6)
C19—Ho1—N2—C35	73.5 (3)	Ho1—N1—C37—C36	168.9 (3)
C1—Ho1—N2—C35	−101.2 (3)	C28—N1—C37—C39	179.0 (4)
Ho1ⁱ—Ho1—N2—C35	−53.7 (4)	Ho1—N1—C37—C39	−11.2 (4)
O1ⁱ—Ho1—N2—C39	−170.3 (2)	C30—C36—C37—N1	1.3 (6)
O5—Ho1—N2—C39	−14.0 (4)	C31—C36—C37—N1	−179.6 (4)
O4—Ho1—N2—C39	139.0 (3)	C30—C36—C37—C39	−178.7 (4)
O8—Ho1—N2—C39	−89.5 (3)	C31—C36—C37—C39	0.5 (6)
O2—Ho1—N2—C39	60.0 (3)	C34—C33—C38—C39	−0.8 (6)
O7—Ho1—N2—C39	−142.8 (3)	C34—C33—C38—C32	−179.5 (4)
N1—Ho1—N2—C39	−11.9 (3)	C31—C32—C38—C39	2.6 (6)
O1—Ho1—N2—C39	82.6 (3)	C31—C32—C38—C33	−178.7 (4)
C19—Ho1—N2—C39	−115.1 (3)	C35—N2—C39—C38	1.2 (6)
C1—Ho1—N2—C39	70.2 (3)	Ho1—N2—C39—C38	−170.5 (3)
Ho1ⁱ—Ho1—N2—C39	117.7 (3)	C35—N2—C39—C37	−177.0 (3)
Ho1—O2—C1—O1	−1.1 (4)	Ho1—N2—C39—C37	11.3 (5)
Ho1—O2—C1—C2	−178.6 (3)	C33—C38—C39—N2	−0.6 (6)
Ho1ⁱ—O1—C1—O2	−159.3 (6)	C32—C38—C39—N2	178.1 (4)
Ho1—O1—C1—O2	1.0 (4)	C33—C38—C39—C37	177.5 (4)
Ho1ⁱ—O1—C1—C2	18.2 (10)	C32—C38—C39—C37	−3.7 (6)
Ho1—O1—C1—C2	178.5 (3)	N1—C37—C39—N2	0.5 (5)
Ho1ⁱ—O1—C1—Ho1	−160.3 (8)	C36—C37—C39—N2	−179.5 (3)
O1ⁱ—Ho1—C1—O2	−173.2 (2)	N1—C37—C39—C38	−177.8 (3)
O5—Ho1—C1—O2	115.4 (2)	C36—C37—C39—C38	2.2 (6)

Symmetry code: (i) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ho₂(C₉H₉O₃)₆(C₁₂H₈N₂)₂]
M_r	1681.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.4657 (2), 25.7960 (3), 13.8366 (2)
β (°)	120.687 (1)
V (Å³)	3519.37 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.31
Crystal size (mm)	0.25 × 0.16 × 0.06

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.656, 0.877
No. of measured, independent and observed [I > 2σ(I)] reflections	24604, 6189, 4266
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.062, 1.00
No. of reflections	6189
No. of parameters	464
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.55

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Markus, D. M. & Buser, H. R. (1997). Environ. Sci. Technol. 31, 1953–1959. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Shen, J.-B., Liu, J.-L. & Zhao, G.-L. (2011b). Acta Cryst. E67, m1319. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Zhao, G.-L., Liu, J.-L. & Liu, J.-F. (2010). Acta Cryst. E66, m1272–m1273. Web of Science CSD CrossRef IUCr Journals Google Scholar

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