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Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1272–m1273.
Published online 2010 September 18. doi:  10.1107/S1600536810036408
PMCID: PMC2983278

Tetra­kis(μ-3,4-dimeth­oxy­phenyl­acetato)­bis­[(3,4-dimeth­oxy­phenyl­acetato)(1,10-phenanthroline)holmium(III)]

Abstract

In the centrosymmetric title compound, [Ho2(C10H11O4)6(C12H8N2)2], the HoIII atom is nine-coordinated by seven O atoms from the 3,4-dimeth­oxy­phenyl­acetate (L) anions and two N atoms from a 1,10-phenanthroline (phen) mol­ecule. The L ligands are coordinated to the HoIII ions in three modes: chelating, bridging and bridging–tridentate. Intra­molecular C—H(...)O inter­actions occur. The crystal packing is stabilized by inter­molecular C—H(...)O inter­actions and weak aromatic π–π inter­actions between phen mol­ecules and the aromatic rings of the L ligands [centroid–centroid distance = 3.821 (2) Å].

Related literature

For related structures, see: Li et al. (2005 [triangle]); Li & Zou (2005 [triangle]); Wang et al. (2010 [triangle]); Liu et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1272-scheme1.jpg

Experimental

Crystal data

  • [Ho2(C10H11O4)6(C12H8N2)2]
  • M r = 1861.40
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1272-efi1.jpg
  • a = 12.3069 (2) Å
  • b = 12.3789 (2) Å
  • c = 14.6591 (2) Å
  • α = 91.020 (1)°
  • β = 103.547 (1)°
  • γ = 115.477 (1)°
  • V = 1942.03 (5) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.11 mm−1
  • T = 296 K
  • 0.30 × 0.16 × 0.05 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.676, T max = 0.909
  • 31540 measured reflections
  • 8930 independent reflections
  • 7217 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.068
  • S = 1.04
  • 8930 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.92 e Å−3
  • Δρmin = −0.57 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810036408/pv2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036408/pv2299Isup2.hkl

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

supplementary crystallographic information

Comment

The rare earth complexes with aromatic carboxylates have a variety of structures due to the various coordination modes of carboxylate groups, which have received considerable attention for many years (Li & Zou, 2005; Li et al., 2005). We have reported some similar mixed-ligands lanthanide carboxylate complexes with dimeric structures (Wang et al., 2010; Liu et al., 2010). We have now prepared a new holmium complex [Ho(L)3phen]2, wherein L = 3,4-dimethoxyphenylacetate and phen = 1,10-phenanthroline]. In this paper, the crystal structure of the title complex is reported.

The structure of the title complex is shown in Fig. 1. It is a centrosymmetric dimer which consists of six 3,4-dimethoxyphenylacetate anions, two 1,10-phenanthroline molecules and two HoIII ions. The HoIII ion is nine-coordinated by two N atoms from one 1,10-phenanthroline and seven O atoms from carboxylate groups with a mean Ho—O bond length of 2.400 (2) Å. The ligands (L) are coordinated to the HoIII ions in three different modes: chelating, bridging and bridging tridentate. Around each HoIII, there is one L ligand in chelating mode through two O atoms from the carboxyl group. Two symmetric L ligands bridge the two Ho centers though carboxyl O atoms. Two L ligands in bidentate mode form bonds with HoIII ion with two carboxyl O atoms and simultaneously bond to another HoIII ion with one of the carboxyl O atom. The Ho—Ho separation is 3.8741 (3) Å. The packing plot of the title complex is shown in Fig. 2. The most significant forces contribulting to the formation and stabilization of the crystal packing are intermolecular interactions of the type C—H···O hydrogen bonds and weak π–π aromatic interactions from phen molecules and aromatic rings of the L ligands. The ring [N(2)/C(40)—C(41)] stacks with its symmetry related ring of an adjacent molecule. The distance of Cg and Cg* [* = -x, 1-y, -z] being 3.821 (2) Å, where Cg is the center of the ring.

Experimental

A mixture of 3,4-dimethoxyphenylacetic acid (0.5886 g, 3 mmol), Ho2O3 (0.1889 g, 0.5 mmol), 1,10-phenanthroline (0.1982 g, 1 mmol) and purified water (20 ml) was sealed in a 25 ml stainless steel reactor and kept at 433 K for 3 d. The reactor was cooled to room temperature at a speed of 5 ° per hour. A few colourless single crystals were obtained from the solution.

Refinement

The H atoms were positioned geometrically and refined using a riding model with C—H distances 0.93, 0.96 and 0.97 Å for aryl, methyl and methylene τype H-atoms, respectvely, and Uiso(H) = 1.5Ueq(methyl C) or 1.2Ueq(methylene and aryl C)

Figures

Fig. 1.
The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level and H-atoms have been excluded for clarity. Symmetry code for atoms with labels ending in A: -x+1, -y+1, -z.
Fig. 2.
The packing plot of the title complex.

Crystal data

[Ho2(C10H11O4)6(C12H8N2)2]Z = 1
Mr = 1861.40F(000) = 940
Triclinic, P1Dx = 1.592 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3069 (2) ÅCell parameters from 6803 reflections
b = 12.3789 (2) Åθ = 1.4–27.6°
c = 14.6591 (2) ŵ = 2.11 mm1
α = 91.020 (1)°T = 296 K
β = 103.547 (1)°Block, colourless
γ = 115.477 (1)°0.30 × 0.16 × 0.05 mm
V = 1942.03 (5) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer8930 independent reflections
Radiation source: fine-focus sealed tube7217 reflections with I > 2σ(I)
graphiteRint = 0.048
[var phi] and ω scansθmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→15
Tmin = 0.676, Tmax = 0.909k = −16→16
31540 measured reflectionsl = −18→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.068H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0272P)2] where P = (Fo2 + 2Fc2)/3
8930 reflections(Δ/σ)max = 0.001
514 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = −0.57 e Å3

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 (Å2)

xyzUiso*/Ueq
Ho0.322299 (13)0.394135 (14)−0.031917 (10)0.03732 (6)
N10.1393 (2)0.3395 (2)−0.18380 (19)0.0423 (6)
O10.3971 (2)−0.0570 (3)0.33827 (19)0.0714 (8)
C10.4836 (4)−0.0673 (4)0.2938 (3)0.0801 (13)
H1A0.5372−0.09280.33670.120*
H1B0.53310.00960.27660.120*
H1C0.4391−0.12570.23790.120*
N20.1144 (2)0.3556 (2)−0.0045 (2)0.0460 (7)
O20.2650 (3)−0.0150 (3)0.43207 (18)0.0762 (8)
C20.3127 (3)−0.0213 (3)0.2872 (3)0.0519 (9)
O30.2761 (2)0.2511 (2)0.08389 (15)0.0446 (5)
C30.2930 (3)−0.0101 (3)0.1925 (2)0.0506 (8)
H3A0.3412−0.02570.15870.061*
O40.2375 (2)0.1805 (2)−0.06397 (15)0.0523 (6)
C40.2034 (3)0.0236 (3)0.1462 (2)0.0482 (8)
O50.1107 (2)0.7367 (2)−0.36823 (16)0.0632 (7)
C50.1341 (3)0.0471 (3)0.1985 (3)0.0586 (10)
H5A0.07350.07020.16860.070*
O60.1314 (2)0.9430 (2)−0.30608 (15)0.0489 (6)
C60.1524 (4)0.0372 (3)0.2934 (3)0.0594 (10)
H6A0.10520.05440.32710.071*
O70.29365 (19)0.57028 (19)−0.08541 (15)0.0450 (5)
C70.2409 (3)0.0017 (3)0.3386 (2)0.0521 (9)
O80.48677 (19)0.59853 (19)−0.04397 (14)0.0429 (5)
C80.1892 (5)−0.0028 (5)0.4850 (3)0.0941 (15)
H8A0.2158−0.01670.54880.141*
H8B0.1040−0.06060.45720.141*
H8C0.19560.07730.48540.141*
O90.6574 (3)0.3196 (3)0.50641 (19)0.0787 (8)
C90.1854 (4)0.0357 (3)0.0430 (2)0.0548 (9)
H9A0.0968−0.00570.01150.066*
H9B0.2257−0.00480.01670.066*
C100.2361 (3)0.1644 (3)0.0208 (2)0.0411 (7)
O100.7495 (3)0.5463 (3)0.5641 (2)0.0917 (10)
C110.0784 (4)0.6144 (3)−0.3965 (3)0.0790 (14)
H11A0.01670.5865−0.45660.118*
H11B0.04530.5662−0.35010.118*
H11C0.15150.6075−0.40210.118*
O110.5943 (2)0.6253 (2)0.15514 (14)0.0491 (6)
C120.1977 (3)0.7908 (3)−0.2841 (2)0.0404 (7)
O120.3859 (2)0.5183 (2)0.11182 (15)0.0440 (5)
C130.2748 (3)0.7456 (3)−0.2339 (2)0.0414 (7)
H13A0.26980.6732−0.25810.050*
C140.3601 (3)0.8069 (3)−0.1476 (2)0.0421 (7)
C150.3611 (3)0.9104 (3)−0.1123 (2)0.0547 (9)
H15A0.41360.9494−0.05280.066*
C160.2862 (3)0.9592 (3)−0.1626 (2)0.0495 (9)
H16A0.29051.0309−0.13750.059*
C170.2062 (3)0.9011 (3)−0.2490 (2)0.0375 (7)
C180.1639 (4)1.0674 (3)−0.2852 (2)0.0566 (10)
H18A0.10611.0873−0.32900.085*
H18B0.24691.1155−0.29070.085*
H18C0.16061.0833−0.22180.085*
C190.4543 (3)0.7644 (3)−0.0977 (3)0.0516 (9)
H19A0.51090.7745−0.13670.062*
H19B0.50330.8180−0.03880.062*
C200.4062 (3)0.6372 (3)−0.0751 (2)0.0369 (7)
C210.6063 (5)0.1934 (4)0.4770 (3)0.0975 (16)
H21A0.64400.15790.52410.146*
H21B0.62280.18060.41790.146*
H21C0.51780.15670.46920.146*
C220.6133 (3)0.3835 (4)0.4469 (2)0.0568 (9)
C230.5234 (4)0.3343 (4)0.3615 (3)0.0631 (10)
H23A0.48960.25220.34090.076*
C240.4832 (4)0.4065 (3)0.3063 (2)0.0569 (9)
H24A0.42250.37230.24900.068*
C250.5318 (3)0.5279 (3)0.3352 (2)0.0463 (8)
C260.6210 (3)0.5777 (4)0.4211 (2)0.0560 (9)
H26A0.65440.65990.44150.067*
C270.6610 (3)0.5055 (4)0.4772 (3)0.0598 (10)
C280.7925 (5)0.6654 (5)0.6041 (3)0.0988 (17)
H28A0.85300.68150.66380.148*
H28B0.72360.67720.61360.148*
H28C0.83040.71950.56220.148*
C290.4864 (3)0.6051 (3)0.2731 (2)0.0514 (9)
H29A0.53960.68980.29740.062*
H29B0.40200.58680.27470.062*
C300.4886 (3)0.5814 (3)0.1712 (2)0.0426 (8)
C310.1508 (3)0.3323 (3)−0.2708 (2)0.0501 (8)
H31A0.22500.3356−0.27880.060*
C320.0572 (3)0.3199 (3)−0.3513 (3)0.0599 (10)
H32A0.06780.3122−0.41140.072*
C33−0.0500 (3)0.3191 (3)−0.3402 (3)0.0611 (11)
H33A−0.11300.3118−0.39300.073*
C34−0.0651 (3)0.3292 (3)−0.2503 (3)0.0515 (9)
C35−0.1740 (3)0.3324 (3)−0.2336 (4)0.0700 (12)
H35A−0.23630.3308−0.28450.084*
C36−0.1871 (3)0.3376 (3)−0.1459 (4)0.0727 (13)
H36A−0.25880.3393−0.13700.087*
C37−0.0930 (3)0.3408 (3)−0.0650 (3)0.0589 (10)
C38−0.1051 (4)0.3425 (3)0.0270 (4)0.0698 (12)
H38A−0.17710.34040.03840.084*
C39−0.0106 (4)0.3474 (3)0.1002 (3)0.0680 (11)
H39A−0.01890.34500.16160.082*
C400.0991 (4)0.3561 (3)0.0812 (3)0.0586 (10)
H40A0.16430.36250.13180.070*
C410.0185 (3)0.3453 (3)−0.0790 (3)0.0469 (8)
C420.0318 (3)0.3382 (3)−0.1724 (2)0.0427 (8)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ho0.03932 (9)0.05518 (10)0.03659 (8)0.03442 (8)0.01714 (6)0.01890 (6)
N10.0390 (15)0.0474 (16)0.0518 (16)0.0277 (13)0.0149 (12)0.0178 (13)
O10.0688 (18)0.093 (2)0.0748 (18)0.0511 (17)0.0269 (15)0.0375 (16)
C10.066 (3)0.085 (3)0.104 (4)0.044 (3)0.027 (3)0.022 (3)
N20.0441 (16)0.0546 (17)0.0583 (17)0.0318 (14)0.0273 (14)0.0200 (14)
O20.084 (2)0.112 (2)0.0462 (15)0.0508 (18)0.0265 (14)0.0322 (15)
C20.052 (2)0.051 (2)0.055 (2)0.0238 (18)0.0177 (17)0.0207 (17)
O30.0548 (14)0.0514 (14)0.0384 (12)0.0304 (12)0.0179 (10)0.0136 (11)
C30.062 (2)0.047 (2)0.053 (2)0.0265 (18)0.0280 (18)0.0170 (16)
O40.0747 (17)0.0616 (15)0.0350 (12)0.0401 (14)0.0204 (11)0.0174 (11)
C40.060 (2)0.0419 (19)0.0453 (19)0.0216 (17)0.0204 (17)0.0159 (15)
O50.0823 (18)0.0458 (15)0.0519 (14)0.0359 (14)−0.0129 (13)−0.0013 (11)
C50.065 (2)0.068 (3)0.055 (2)0.037 (2)0.0204 (19)0.0264 (19)
O60.0580 (14)0.0515 (14)0.0470 (13)0.0383 (12)0.0038 (11)0.0108 (11)
C60.070 (3)0.072 (3)0.055 (2)0.041 (2)0.0306 (19)0.0192 (19)
O70.0383 (12)0.0530 (14)0.0573 (14)0.0313 (11)0.0146 (10)0.0205 (11)
C70.057 (2)0.058 (2)0.0423 (19)0.0227 (19)0.0193 (17)0.0169 (17)
O80.0449 (12)0.0639 (15)0.0438 (12)0.0420 (12)0.0187 (10)0.0231 (11)
C80.128 (4)0.120 (4)0.053 (3)0.063 (4)0.041 (3)0.025 (3)
O90.095 (2)0.079 (2)0.0620 (17)0.0491 (18)−0.0004 (15)0.0195 (15)
C90.070 (2)0.048 (2)0.0428 (19)0.0224 (19)0.0157 (17)0.0135 (16)
C100.0415 (18)0.056 (2)0.0399 (18)0.0323 (17)0.0138 (14)0.0167 (16)
O100.096 (2)0.083 (2)0.079 (2)0.0447 (19)−0.0164 (18)−0.0074 (17)
C110.094 (3)0.049 (2)0.075 (3)0.033 (2)−0.013 (2)−0.013 (2)
O110.0441 (13)0.0771 (17)0.0401 (12)0.0366 (13)0.0169 (10)0.0145 (11)
C120.0457 (18)0.0407 (18)0.0369 (17)0.0226 (15)0.0077 (14)0.0118 (14)
O120.0438 (13)0.0596 (14)0.0450 (12)0.0332 (12)0.0206 (11)0.0150 (11)
C130.0450 (18)0.0344 (17)0.0501 (19)0.0212 (15)0.0147 (15)0.0109 (14)
C140.0394 (17)0.0439 (19)0.0482 (19)0.0238 (15)0.0101 (14)0.0148 (15)
C150.059 (2)0.057 (2)0.0455 (19)0.0353 (19)−0.0074 (17)−0.0023 (17)
C160.060 (2)0.053 (2)0.0446 (19)0.0390 (19)0.0057 (16)0.0017 (16)
C170.0413 (17)0.0442 (18)0.0391 (17)0.0281 (15)0.0140 (14)0.0142 (14)
C180.076 (3)0.056 (2)0.056 (2)0.048 (2)0.0122 (19)0.0164 (17)
C190.0405 (18)0.052 (2)0.067 (2)0.0290 (17)0.0053 (16)0.0135 (18)
C200.0438 (19)0.053 (2)0.0304 (15)0.0353 (17)0.0119 (13)0.0130 (14)
C210.123 (4)0.079 (3)0.091 (4)0.050 (3)0.015 (3)0.041 (3)
C220.063 (2)0.068 (3)0.042 (2)0.034 (2)0.0111 (17)0.0163 (18)
C230.078 (3)0.058 (2)0.050 (2)0.032 (2)0.0083 (19)0.0124 (18)
C240.069 (2)0.062 (2)0.0396 (19)0.032 (2)0.0085 (17)0.0106 (17)
C250.052 (2)0.065 (2)0.0370 (17)0.0344 (19)0.0230 (15)0.0170 (16)
C260.061 (2)0.063 (2)0.046 (2)0.030 (2)0.0136 (17)0.0060 (18)
C270.058 (2)0.078 (3)0.047 (2)0.036 (2)0.0063 (18)0.0130 (19)
C280.094 (4)0.113 (4)0.069 (3)0.042 (3)−0.004 (3)−0.023 (3)
C290.064 (2)0.068 (2)0.0447 (19)0.045 (2)0.0251 (17)0.0146 (17)
C300.051 (2)0.061 (2)0.0394 (17)0.0409 (18)0.0209 (16)0.0197 (16)
C310.052 (2)0.056 (2)0.049 (2)0.0308 (18)0.0127 (16)0.0178 (17)
C320.062 (2)0.065 (2)0.051 (2)0.033 (2)0.0030 (18)0.0132 (18)
C330.049 (2)0.051 (2)0.069 (3)0.0219 (19)−0.0097 (19)0.0106 (19)
C340.0367 (18)0.0367 (19)0.074 (3)0.0171 (16)0.0015 (17)0.0056 (17)
C350.037 (2)0.055 (2)0.111 (4)0.0254 (19)−0.001 (2)0.000 (2)
C360.0298 (19)0.058 (3)0.132 (4)0.0247 (19)0.014 (2)−0.002 (3)
C370.039 (2)0.039 (2)0.105 (3)0.0183 (17)0.028 (2)0.004 (2)
C380.047 (2)0.057 (2)0.125 (4)0.029 (2)0.047 (3)0.010 (2)
C390.071 (3)0.066 (3)0.092 (3)0.035 (2)0.057 (3)0.017 (2)
C400.058 (2)0.072 (3)0.068 (2)0.038 (2)0.037 (2)0.022 (2)
C410.0342 (17)0.0343 (18)0.079 (3)0.0187 (15)0.0201 (17)0.0131 (17)
C420.0341 (17)0.0342 (17)0.063 (2)0.0193 (14)0.0112 (15)0.0112 (15)

Geometric parameters (Å, °)

Ho—O8i2.3142 (18)C12—C131.377 (4)
Ho—O11i2.332 (2)C12—C171.403 (4)
Ho—O122.343 (2)O12—C301.255 (4)
Ho—O42.378 (2)C13—C141.391 (4)
Ho—O32.456 (2)C13—H13A0.9300
Ho—O72.4670 (19)C14—C151.367 (4)
Ho—O82.511 (2)C14—C191.516 (4)
Ho—N22.524 (2)C15—C161.391 (4)
Ho—N12.603 (2)C15—H15A0.9300
Ho—C102.770 (3)C16—C171.366 (4)
Ho—C202.867 (3)C16—H16A0.9300
Ho—Hoi3.8741 (3)C18—H18A0.9600
N1—C311.322 (4)C18—H18B0.9600
N1—C421.366 (4)C18—H18C0.9600
O1—C21.370 (4)C19—C201.500 (4)
O1—C11.419 (5)C19—H19A0.9700
C1—H1A0.9600C19—H19B0.9700
C1—H1B0.9600C21—H21A0.9600
C1—H1C0.9600C21—H21B0.9600
N2—C401.314 (4)C21—H21C0.9600
N2—C411.365 (4)C22—C231.382 (5)
O2—C71.372 (4)C22—C271.383 (5)
O2—C81.397 (5)C23—C241.384 (5)
C2—C31.372 (5)C23—H23A0.9300
C2—C71.395 (5)C24—C251.371 (5)
O3—C101.244 (4)C24—H24A0.9300
C3—C41.381 (4)C25—C261.384 (5)
C3—H3A0.9300C25—C291.517 (4)
O4—C101.264 (4)C26—C271.389 (5)
C4—C51.383 (5)C26—H26A0.9300
C4—C91.496 (4)C28—H28A0.9600
O5—C121.361 (3)C28—H28B0.9600
O5—C111.416 (4)C28—H28C0.9600
C5—C61.372 (5)C29—C301.527 (4)
C5—H5A0.9300C29—H29A0.9700
O6—C171.372 (3)C29—H29B0.9700
O6—C181.421 (4)C31—C321.395 (4)
C6—C71.380 (5)C31—H31A0.9300
C6—H6A0.9300C32—C331.362 (5)
O7—C201.240 (4)C32—H32A0.9300
O8—C201.275 (3)C33—C341.384 (5)
O8—Hoi2.3142 (18)C33—H33A0.9300
C8—H8A0.9600C34—C421.408 (4)
C8—H8B0.9600C34—C351.433 (5)
C8—H8C0.9600C35—C361.337 (6)
O9—C221.361 (4)C35—H35A0.9300
O9—C211.423 (5)C36—C371.437 (6)
C9—C101.514 (5)C36—H36A0.9300
C9—H9A0.9700C37—C381.391 (6)
C9—H9B0.9700C37—C411.413 (4)
O10—C271.385 (4)C38—C391.363 (6)
O10—C281.396 (5)C38—H38A0.9300
C11—H11A0.9600C39—C401.402 (5)
C11—H11B0.9600C39—H39A0.9300
C11—H11C0.9600C40—H40A0.9300
O11—C301.258 (4)C41—C421.422 (5)
O11—Hoi2.332 (2)
O8i—Ho—O11i75.86 (7)O4—C10—Ho58.91 (17)
O8i—Ho—O1275.67 (7)C9—C10—Ho176.4 (2)
O11i—Ho—O12138.40 (8)C27—O10—C28118.2 (3)
O8i—Ho—O489.15 (8)O5—C11—H11A109.5
O11i—Ho—O479.00 (8)O5—C11—H11B109.5
O12—Ho—O4129.94 (7)H11A—C11—H11B109.5
O8i—Ho—O375.22 (7)O5—C11—H11C109.5
O11i—Ho—O3123.94 (7)H11A—C11—H11C109.5
O12—Ho—O376.21 (7)H11B—C11—H11C109.5
O4—Ho—O353.75 (7)C30—O11—Hoi137.0 (2)
O8i—Ho—O7124.23 (7)O5—C12—C13125.1 (3)
O11i—Ho—O793.63 (8)O5—C12—C17115.0 (3)
O12—Ho—O778.23 (7)C13—C12—C17119.9 (3)
O4—Ho—O7143.26 (7)C30—O12—Ho135.23 (19)
O3—Ho—O7142.10 (7)C12—C13—C14120.9 (3)
O8i—Ho—O873.27 (7)C12—C13—H13A119.5
O11i—Ho—O871.50 (8)C14—C13—H13A119.5
O12—Ho—O871.63 (7)C15—C14—C13118.0 (3)
O4—Ho—O8148.46 (7)C15—C14—C19121.1 (3)
O3—Ho—O8139.35 (7)C13—C14—C19120.8 (3)
O7—Ho—O851.86 (6)C14—C15—C16122.1 (3)
O8i—Ho—N2141.50 (8)C14—C15—H15A118.9
O11i—Ho—N2139.60 (8)C16—C15—H15A118.9
O12—Ho—N278.71 (8)C17—C16—C15119.6 (3)
O4—Ho—N285.70 (8)C17—C16—H16A120.2
O3—Ho—N271.06 (8)C15—C16—H16A120.2
O7—Ho—N276.86 (8)C16—C17—O6124.6 (3)
O8—Ho—N2124.29 (7)C16—C17—C12119.3 (3)
O8i—Ho—N1150.25 (8)O6—C17—C12116.1 (3)
O11i—Ho—N175.80 (8)O6—C18—H18A109.5
O12—Ho—N1133.15 (7)O6—C18—H18B109.5
O4—Ho—N176.77 (8)H18A—C18—H18B109.5
O3—Ho—N1114.33 (8)O6—C18—H18C109.5
O7—Ho—N166.55 (7)H18A—C18—H18C109.5
O8—Ho—N1105.76 (7)H18B—C18—H18C109.5
N2—Ho—N164.32 (9)C20—C19—C14118.1 (3)
O8i—Ho—C1081.66 (8)C20—C19—H19A107.8
O11i—Ho—C10102.29 (9)C14—C19—H19A107.8
O12—Ho—C10102.89 (9)C20—C19—H19B107.8
O4—Ho—C1027.08 (8)C14—C19—H19B107.8
O3—Ho—C1026.68 (8)H19A—C19—H19B107.1
O7—Ho—C10152.62 (8)O7—C20—O8120.0 (3)
O8—Ho—C10154.93 (7)O7—C20—C19123.0 (2)
N2—Ho—C1076.58 (8)O8—C20—C19117.0 (3)
N1—Ho—C1095.73 (8)O7—C20—Ho58.91 (15)
O8i—Ho—C2099.25 (8)O8—C20—Ho61.05 (16)
O11i—Ho—C2081.94 (8)C19—C20—Ho178.0 (2)
O12—Ho—C2073.44 (8)O9—C21—H21A109.5
O4—Ho—C20156.61 (8)O9—C21—H21B109.5
O3—Ho—C20149.55 (8)H21A—C21—H21B109.5
O7—Ho—C2025.49 (7)O9—C21—H21C109.5
O8—Ho—C2026.38 (7)H21A—C21—H21C109.5
N2—Ho—C20100.42 (8)H21B—C21—H21C109.5
N1—Ho—C2085.54 (8)O9—C22—C23124.6 (4)
C10—Ho—C20175.76 (9)O9—C22—C27116.4 (3)
O8i—Ho—Hoi38.38 (5)C23—C22—C27119.0 (3)
O11i—Ho—Hoi69.41 (5)C22—C23—C24120.4 (4)
O12—Ho—Hoi69.39 (5)C22—C23—H23A119.8
O4—Ho—Hoi122.93 (6)C24—C23—H23A119.8
O3—Ho—Hoi109.84 (5)C25—C24—C23120.8 (3)
O7—Ho—Hoi86.31 (5)C25—C24—H24A119.6
O8—Ho—Hoi34.89 (4)C23—C24—H24A119.6
N2—Ho—Hoi146.38 (6)C24—C25—C26119.1 (3)
N1—Ho—Hoi134.01 (6)C24—C25—C29119.7 (3)
C10—Ho—Hoi120.04 (6)C26—C25—C29121.2 (3)
C20—Ho—Hoi61.00 (6)C25—C26—C27120.3 (4)
C31—N1—C42118.1 (3)C25—C26—H26A119.8
C31—N1—Ho123.9 (2)C27—C26—H26A119.8
C42—N1—Ho117.1 (2)C22—C27—O10114.8 (3)
C2—O1—C1117.6 (3)C22—C27—C26120.3 (3)
O1—C1—H1A109.5O10—C27—C26124.8 (4)
O1—C1—H1B109.5O10—C28—H28A109.5
H1A—C1—H1B109.5O10—C28—H28B109.5
O1—C1—H1C109.5H28A—C28—H28B109.5
H1A—C1—H1C109.5O10—C28—H28C109.5
H1B—C1—H1C109.5H28A—C28—H28C109.5
C40—N2—C41118.5 (3)H28B—C28—H28C109.5
C40—N2—Ho121.5 (2)C25—C29—C30110.6 (3)
C41—N2—Ho119.7 (2)C25—C29—H29A109.5
C7—O2—C8118.0 (3)C30—C29—H29A109.5
O1—C2—C3125.5 (3)C25—C29—H29B109.5
O1—C2—C7114.8 (3)C30—C29—H29B109.5
C3—C2—C7119.7 (3)H29A—C29—H29B108.1
C10—O3—Ho90.89 (18)O12—C30—O11126.1 (3)
C2—C3—C4121.5 (3)O12—C30—C29117.4 (3)
C2—C3—H3A119.2O11—C30—C29116.4 (3)
C4—C3—H3A119.2N1—C31—C32123.2 (3)
C10—O4—Ho94.0 (2)N1—C31—H31A118.4
C3—C4—C5117.9 (3)C32—C31—H31A118.4
C3—C4—C9119.9 (3)C33—C32—C31118.9 (4)
C5—C4—C9122.2 (3)C33—C32—H32A120.6
C12—O5—C11117.2 (3)C31—C32—H32A120.6
C6—C5—C4121.7 (3)C32—C33—C34120.0 (3)
C6—C5—H5A119.2C32—C33—H33A120.0
C4—C5—H5A119.2C34—C33—H33A120.0
C17—O6—C18116.1 (2)C33—C34—C42118.1 (3)
C5—C6—C7119.9 (3)C33—C34—C35122.8 (4)
C5—C6—H6A120.0C42—C34—C35119.1 (4)
C7—C6—H6A120.0C36—C35—C34121.0 (4)
C20—O7—Ho95.61 (16)C36—C35—H35A119.5
O2—C7—C6125.3 (3)C34—C35—H35A119.5
O2—C7—C2115.5 (3)C35—C36—C37121.5 (4)
C6—C7—C2119.3 (3)C35—C36—H36A119.3
C20—O8—Hoi158.2 (2)C37—C36—H36A119.3
C20—O8—Ho92.57 (19)C38—C37—C41118.2 (4)
Hoi—O8—Ho106.73 (7)C38—C37—C36123.2 (4)
O2—C8—H8A109.5C41—C37—C36118.6 (4)
O2—C8—H8B109.5C39—C38—C37119.6 (3)
H8A—C8—H8B109.5C39—C38—H38A120.2
O2—C8—H8C109.5C37—C38—H38A120.2
H8A—C8—H8C109.5C38—C39—C40118.9 (4)
H8B—C8—H8C109.5C38—C39—H39A120.6
C22—O9—C21116.7 (3)C40—C39—H39A120.6
C4—C9—C10114.9 (3)N2—C40—C39123.3 (4)
C4—C9—H9A108.5N2—C40—H40A118.4
C10—C9—H9A108.5C39—C40—H40A118.4
C4—C9—H9B108.5N2—C41—C37121.4 (3)
C10—C9—H9B108.5N2—C41—C42118.8 (3)
H9A—C9—H9B107.5C37—C41—C42119.8 (3)
O3—C10—O4121.3 (3)N1—C42—C34121.7 (3)
O3—C10—C9121.1 (3)N1—C42—C41118.4 (3)
O4—C10—C9117.6 (3)C34—C42—C41119.9 (3)
O3—C10—Ho62.44 (17)
O8i—Ho—N1—C31−25.1 (3)O8i—Ho—C10—O4−104.69 (18)
O11i—Ho—N1—C31−7.1 (2)O11i—Ho—C10—O4−31.22 (19)
O12—Ho—N1—C31138.0 (2)O12—Ho—C10—O4−177.82 (17)
O4—Ho—N1—C31−88.9 (3)O3—Ho—C10—O4−178.3 (3)
O3—Ho—N1—C31−128.2 (2)O7—Ho—C10—O492.9 (2)
O7—Ho—N1—C3193.4 (3)O8—Ho—C10—O4−103.7 (2)
O8—Ho—N1—C3158.6 (3)N2—Ho—C10—O4107.31 (19)
N2—Ho—N1—C31179.6 (3)N1—Ho—C10—O445.45 (19)
C10—Ho—N1—C31−108.3 (3)Hoi—Ho—C10—O4−104.38 (17)
C20—Ho—N1—C3175.7 (2)C11—O5—C12—C1314.0 (5)
Hoi—Ho—N1—C3134.5 (3)C11—O5—C12—C17−166.3 (3)
O8i—Ho—N1—C42166.08 (19)O8i—Ho—O12—C3022.3 (3)
O11i—Ho—N1—C42−175.9 (2)O11i—Ho—O12—C30−25.8 (3)
O12—Ho—N1—C42−30.8 (3)O4—Ho—O12—C3098.8 (3)
O4—Ho—N1—C42102.3 (2)O3—Ho—O12—C30100.3 (3)
O3—Ho—N1—C4263.0 (2)O7—Ho—O12—C30−108.0 (3)
O7—Ho—N1—C42−75.4 (2)O8—Ho—O12—C30−54.5 (3)
O8—Ho—N1—C42−110.2 (2)N2—Ho—O12—C30173.3 (3)
N2—Ho—N1—C4210.8 (2)N1—Ho—O12—C30−149.2 (3)
C10—Ho—N1—C4282.9 (2)C10—Ho—O12—C30100.1 (3)
C20—Ho—N1—C42−93.1 (2)C20—Ho—O12—C30−82.1 (3)
Hoi—Ho—N1—C42−134.35 (19)Hoi—Ho—O12—C30−17.5 (3)
O8i—Ho—N2—C4015.4 (3)O5—C12—C13—C14−179.2 (3)
O11i—Ho—N2—C40166.0 (2)C17—C12—C13—C141.2 (5)
O12—Ho—N2—C40−33.6 (3)C12—C13—C14—C152.8 (5)
O4—Ho—N2—C4098.6 (3)C12—C13—C14—C19−173.3 (3)
O3—Ho—N2—C4045.5 (3)C13—C14—C15—C16−4.3 (5)
O7—Ho—N2—C40−114.0 (3)C19—C14—C15—C16171.8 (3)
O8—Ho—N2—C40−91.9 (3)C14—C15—C16—C171.7 (6)
N1—Ho—N2—C40176.0 (3)C15—C16—C17—O6−177.6 (3)
C10—Ho—N2—C4072.8 (3)C15—C16—C17—C122.3 (5)
C20—Ho—N2—C40−104.2 (3)C18—O6—C17—C1617.2 (5)
Hoi—Ho—N2—C40−52.0 (3)C18—O6—C17—C12−162.7 (3)
O8i—Ho—N2—C41−170.87 (19)O5—C12—C17—C16176.6 (3)
O11i—Ho—N2—C41−20.2 (3)C13—C12—C17—C16−3.8 (5)
O12—Ho—N2—C41140.1 (2)O5—C12—C17—O6−3.5 (4)
O4—Ho—N2—C41−87.7 (2)C13—C12—C17—O6176.2 (3)
O3—Ho—N2—C41−140.7 (2)C15—C14—C19—C20127.4 (4)
O7—Ho—N2—C4159.8 (2)C13—C14—C19—C20−56.6 (5)
O8—Ho—N2—C4181.8 (2)Ho—O7—C20—O8−0.6 (3)
N1—Ho—N2—C41−10.3 (2)Ho—O7—C20—C19179.3 (3)
C10—Ho—N2—C41−113.5 (2)Hoi—O8—C20—O7−151.9 (4)
C20—Ho—N2—C4169.6 (2)Ho—O8—C20—O70.6 (3)
Hoi—Ho—N2—C41121.7 (2)Hoi—O8—C20—C1928.1 (7)
C1—O1—C2—C39.3 (5)Ho—O8—C20—C19−179.3 (2)
C1—O1—C2—C7−172.3 (3)Hoi—O8—C20—Ho−152.5 (5)
O8i—Ho—O3—C10−101.02 (18)C14—C19—C20—O7−8.4 (5)
O11i—Ho—O3—C10−39.8 (2)C14—C19—C20—O8171.5 (3)
O12—Ho—O3—C10−179.55 (18)O8i—Ho—C20—O7−169.38 (17)
O4—Ho—O3—C10−0.98 (17)O11i—Ho—C20—O7116.47 (18)
O7—Ho—O3—C10131.53 (18)O12—Ho—C20—O7−97.44 (18)
O8—Ho—O3—C10−141.18 (16)O4—Ho—C20—O780.8 (3)
N2—Ho—O3—C1097.85 (18)O3—Ho—C20—O7−92.9 (2)
N1—Ho—O3—C1049.00 (19)O8—Ho—C20—O7−179.4 (3)
C20—Ho—O3—C10175.93 (17)N2—Ho—C20—O7−22.65 (19)
Hoi—Ho—O3—C10−117.85 (16)N1—Ho—C20—O740.21 (18)
O1—C2—C3—C4178.4 (3)Hoi—Ho—C20—O7−172.7 (2)
C7—C2—C3—C40.0 (5)O8i—Ho—C20—O810.0 (2)
O8i—Ho—O4—C1073.18 (18)O11i—Ho—C20—O8−64.16 (16)
O11i—Ho—O4—C10148.94 (19)O12—Ho—C20—O881.94 (16)
O12—Ho—O4—C102.8 (2)O4—Ho—C20—O8−99.8 (2)
O3—Ho—O4—C100.96 (16)O3—Ho—C20—O886.5 (2)
O7—Ho—O4—C10−129.84 (18)O7—Ho—C20—O8179.4 (3)
O8—Ho—O4—C10128.11 (18)N2—Ho—C20—O8156.73 (16)
N2—Ho—O4—C10−68.64 (19)N1—Ho—C20—O8−140.42 (17)
N1—Ho—O4—C10−133.25 (19)Hoi—Ho—C20—O86.72 (14)
C20—Ho—O4—C10−175.08 (19)C21—O9—C22—C230.3 (6)
Hoi—Ho—O4—C1092.49 (18)C21—O9—C22—C27178.4 (4)
C2—C3—C4—C50.6 (5)O9—C22—C23—C24179.1 (4)
C2—C3—C4—C9179.6 (3)C27—C22—C23—C241.1 (6)
C3—C4—C5—C6−0.2 (5)C22—C23—C24—C250.1 (6)
C9—C4—C5—C6−179.2 (3)C23—C24—C25—C26−0.8 (5)
C4—C5—C6—C7−0.7 (6)C23—C24—C25—C29179.8 (3)
O8i—Ho—O7—C2012.7 (2)C24—C25—C26—C270.3 (5)
O11i—Ho—O7—C20−62.64 (18)C29—C25—C26—C27179.7 (3)
O12—Ho—O7—C2076.13 (18)O9—C22—C27—O101.0 (5)
O4—Ho—O7—C20−139.07 (18)C23—C22—C27—O10179.2 (4)
O3—Ho—O7—C20124.53 (18)O9—C22—C27—C26−179.8 (3)
O8—Ho—O7—C200.35 (16)C23—C22—C27—C26−1.6 (6)
N2—Ho—O7—C20157.12 (19)C28—O10—C27—C22−173.4 (4)
N1—Ho—O7—C20−135.5 (2)C28—O10—C27—C267.4 (6)
C10—Ho—O7—C20171.47 (19)C25—C26—C27—C220.9 (6)
Hoi—Ho—O7—C206.43 (17)C25—C26—C27—O10−180.0 (3)
C8—O2—C7—C64.3 (6)C24—C25—C29—C30−49.1 (4)
C8—O2—C7—C2−174.9 (4)C26—C25—C29—C30131.4 (3)
C5—C6—C7—O2−177.9 (4)Ho—O12—C30—O1124.1 (5)
C5—C6—C7—C21.3 (6)Ho—O12—C30—C29−154.3 (2)
O1—C2—C7—O2−0.2 (5)Hoi—O11—C30—O12−10.5 (5)
C3—C2—C7—O2178.3 (3)Hoi—O11—C30—C29167.9 (2)
O1—C2—C7—C6−179.5 (3)C25—C29—C30—O12104.4 (3)
C3—C2—C7—C6−0.9 (5)C25—C29—C30—O11−74.2 (4)
O8i—Ho—O8—C20−169.7 (2)C42—N1—C31—C32−1.9 (5)
O11i—Ho—O8—C20110.00 (17)Ho—N1—C31—C32−170.6 (3)
O12—Ho—O8—C20−89.62 (17)N1—C31—C32—C332.3 (5)
O4—Ho—O8—C20131.60 (18)C31—C32—C33—C34−0.7 (5)
O3—Ho—O8—C20−129.07 (17)C32—C33—C34—C42−0.9 (5)
O7—Ho—O8—C20−0.34 (16)C32—C33—C34—C35178.2 (3)
N2—Ho—O8—C20−28.05 (19)C33—C34—C35—C36177.5 (4)
N1—Ho—O8—C2041.30 (18)C42—C34—C35—C36−3.4 (6)
C10—Ho—O8—C20−170.7 (2)C34—C35—C36—C370.3 (6)
Hoi—Ho—O8—C20−169.7 (2)C35—C36—C37—C38−178.0 (4)
O8i—Ho—O8—Hoi0.0C35—C36—C37—C413.6 (6)
O11i—Ho—O8—Hoi−80.31 (8)C41—C37—C38—C39−0.5 (5)
O12—Ho—O8—Hoi80.07 (8)C36—C37—C38—C39−179.0 (4)
O4—Ho—O8—Hoi−58.71 (15)C37—C38—C39—C402.9 (6)
O3—Ho—O8—Hoi40.63 (13)C41—N2—C40—C39−0.5 (5)
O7—Ho—O8—Hoi169.35 (12)Ho—N2—C40—C39173.3 (3)
N2—Ho—O8—Hoi141.64 (9)C38—C39—C40—N2−2.4 (6)
N1—Ho—O8—Hoi−149.00 (8)C40—N2—C41—C373.0 (5)
C10—Ho—O8—Hoi−1.0 (2)Ho—N2—C41—C37−171.0 (2)
C20—Ho—O8—Hoi169.7 (2)C40—N2—C41—C42−176.7 (3)
C3—C4—C9—C10−105.6 (4)Ho—N2—C41—C429.4 (4)
C5—C4—C9—C1073.4 (4)C38—C37—C41—N2−2.4 (5)
Ho—O3—C10—O41.7 (3)C36—C37—C41—N2176.1 (3)
Ho—O3—C10—C9−179.1 (3)C38—C37—C41—C42177.2 (3)
Ho—O4—C10—O3−1.8 (3)C36—C37—C41—C42−4.3 (5)
Ho—O4—C10—C9179.0 (2)C31—N1—C42—C340.1 (5)
C4—C9—C10—O3−7.7 (5)Ho—N1—C42—C34169.6 (2)
C4—C9—C10—O4171.5 (3)C31—N1—C42—C41179.7 (3)
O8i—Ho—C10—O373.58 (17)Ho—N1—C42—C41−10.9 (4)
O11i—Ho—C10—O3147.05 (16)C33—C34—C42—N11.3 (5)
O12—Ho—C10—O30.45 (18)C35—C34—C42—N1−177.9 (3)
O4—Ho—C10—O3178.3 (3)C33—C34—C42—C41−178.3 (3)
O7—Ho—C10—O3−88.8 (2)C35—C34—C42—C412.6 (5)
O8—Ho—C10—O374.6 (3)N2—C41—C42—N11.3 (4)
N2—Ho—C10—O3−74.42 (18)C37—C41—C42—N1−178.3 (3)
N1—Ho—C10—O3−136.28 (17)N2—C41—C42—C34−179.1 (3)
Hoi—Ho—C10—O373.89 (18)C37—C41—C42—C341.3 (5)

Symmetry codes: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C40—H40A···O30.932.522.972 (4)110
C8—H8A···O6ii0.962.553.319 (5)138
C16—H16A···O4iii0.932.513.410 (4)162
C18—H18C···O4iii0.962.363.266 (4)156
C21—H21C···O10.962.833.291 (6)111
C21—H21C···O20.962.823.749 (6)162
C31—H31A···O11i0.932.373.008 (4)126
C38—H38A···O7iv0.932.363.215 (4)153

Symmetry codes: (ii) x, y−1, z+1; (iii) x, y+1, z; (i) −x+1, −y+1, −z; (iv) −x, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2299).

References

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