metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages m1272-m1273

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

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

(Received 15 June 2010; accepted 11 September 2010; online 18 September 2010)

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 ππ 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[Li, X., Zhang, Z.-Y. & Song, H.-B. (2005). J. Mol. Struct. 751, 33-40.]); Li & Zou (2005[Li, X. & Zou, Y.-Q. (2005). Z. Kristallogr. New Cryst. Struct. 220, 33-35.]); Wang et al. (2010[Wang, Y.-F., Liu, J.-F. & Zhao, G.-L. (2010). Chin. J. Inorg. Chem. 26, 328-332.]); Liu et al. (2010[Liu, J.-F., Xu, X.-D., Li, H.-Q. & Zhao, G.-L. (2010). Acta Cryst. E66, m291.]).

[Scheme 1]

Experimental

Crystal data
  • [Ho2(C10H11O4)6(C12H8N2)2]

  • Mr = 1861.40

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.676, Tmax = 0.909

  • 31540 measured reflections

  • 8930 independent reflections

  • 7217 reflections with I > 2σ(I)

  • Rint = 0.048

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C40—H40A⋯O3 0.93 2.52 2.972 (4) 110
C8—H8A⋯O6i 0.96 2.55 3.319 (5) 138
C16—H16A⋯O4ii 0.93 2.51 3.410 (4) 162
C18—H18C⋯O4ii 0.96 2.36 3.266 (4) 156
C21—H21C⋯O1 0.96 2.83 3.291 (6) 111
C21—H21C⋯O2 0.96 2.82 3.749 (6) 162
C31—H31A⋯O11iii 0.93 2.37 3.008 (4) 126
C38—H38A⋯O7iv 0.93 2.36 3.215 (4) 153
Symmetry codes: (i) x, y-1, z+1; (ii) x, y+1, z; (iii) -x+1, -y+1, -z; (iv) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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 ππ 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.

Related literature top

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

Experimental top

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 top

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)

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
[Figure 1] 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.
[Figure 2] Fig. 2. The packing plot of the title complex.
Tetrakis(µ-3,4-dimethoxyphenylacetato)bis[(3,4-dimethoxyphenylacetato)(1,10- phenanthroline)holmium(III)] top
Crystal data top
[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 top
Bruker APEXII CCD area-detector
diffractometer
8930 independent reflections
Radiation source: fine-focus sealed tube7217 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ϕ and ω scansθmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1615
Tmin = 0.676, Tmax = 0.909k = 1616
31540 measured reflectionsl = 1819
Refinement top
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 = 1.04 w = 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
Crystal data top
[Ho2(C10H11O4)6(C12H8N2)2]γ = 115.477 (1)°
Mr = 1861.40V = 1942.03 (5) Å3
Triclinic, P1Z = 1
a = 12.3069 (2) ÅMo Kα radiation
b = 12.3789 (2) ŵ = 2.11 mm1
c = 14.6591 (2) ÅT = 296 K
α = 91.020 (1)°0.30 × 0.16 × 0.05 mm
β = 103.547 (1)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
8930 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7217 reflections with I > 2σ(I)
Tmin = 0.676, Tmax = 0.909Rint = 0.048
31540 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.068H-atom parameters constrained
S = 1.04Δρmax = 0.92 e Å3
8930 reflectionsΔρmin = 0.57 e Å3
514 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
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)
H1A0.53720.09280.33670.120*
H1B0.53310.00960.27660.120*
H1C0.43910.12570.23790.120*
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)
H3A0.34120.02570.15870.061*
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)
H8A0.21580.01670.54880.141*
H8B0.10400.06060.45720.141*
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)
H9A0.09680.00570.01150.066*
H9B0.22570.00480.01670.066*
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)
H11A0.01670.58650.45660.118*
H11B0.04530.56620.35010.118*
H11C0.15150.60750.40210.118*
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)
H13A0.26980.67320.25810.050*
C140.3601 (3)0.8069 (3)0.1476 (2)0.0421 (7)
C150.3611 (3)0.9104 (3)0.1123 (2)0.0547 (9)
H15A0.41360.94940.05280.066*
C160.2862 (3)0.9592 (3)0.1626 (2)0.0495 (9)
H16A0.29051.03090.13750.059*
C170.2062 (3)0.9011 (3)0.2490 (2)0.0375 (7)
C180.1639 (4)1.0674 (3)0.2852 (2)0.0566 (10)
H18A0.10611.08730.32900.085*
H18B0.24691.11550.29070.085*
H18C0.16061.08330.22180.085*
C190.4543 (3)0.7644 (3)0.0977 (3)0.0516 (9)
H19A0.51090.77450.13670.062*
H19B0.50330.81800.03880.062*
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)
H31A0.22500.33560.27880.060*
C320.0572 (3)0.3199 (3)0.3513 (3)0.0599 (10)
H32A0.06780.31220.41140.072*
C330.0500 (3)0.3191 (3)0.3402 (3)0.0611 (11)
H33A0.11300.31180.39300.073*
C340.0651 (3)0.3292 (3)0.2503 (3)0.0515 (9)
C350.1740 (3)0.3324 (3)0.2336 (4)0.0700 (12)
H35A0.23630.33080.28450.084*
C360.1871 (3)0.3376 (3)0.1459 (4)0.0727 (13)
H36A0.25880.33930.13700.087*
C370.0930 (3)0.3408 (3)0.0650 (3)0.0589 (10)
C380.1051 (4)0.3425 (3)0.0270 (4)0.0698 (12)
H38A0.17710.34040.03840.084*
C390.0106 (4)0.3474 (3)0.1002 (3)0.0680 (11)
H39A0.01890.34500.16160.082*
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) top
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, º) top
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—C3125.1 (3)O8i—Ho—C10—O4104.69 (18)
O11i—Ho—N1—C317.1 (2)O11i—Ho—C10—O431.22 (19)
O12—Ho—N1—C31138.0 (2)O12—Ho—C10—O4177.82 (17)
O4—Ho—N1—C3188.9 (3)O3—Ho—C10—O4178.3 (3)
O3—Ho—N1—C31128.2 (2)O7—Ho—C10—O492.9 (2)
O7—Ho—N1—C3193.4 (3)O8—Ho—C10—O4103.7 (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—C31108.3 (3)Hoi—Ho—C10—O4104.38 (17)
C20—Ho—N1—C3175.7 (2)C11—O5—C12—C1314.0 (5)
Hoi—Ho—N1—C3134.5 (3)C11—O5—C12—C17166.3 (3)
O8i—Ho—N1—C42166.08 (19)O8i—Ho—O12—C3022.3 (3)
O11i—Ho—N1—C42175.9 (2)O11i—Ho—O12—C3025.8 (3)
O12—Ho—N1—C4230.8 (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—C30108.0 (3)
O7—Ho—N1—C4275.4 (2)O8—Ho—O12—C3054.5 (3)
O8—Ho—N1—C42110.2 (2)N2—Ho—O12—C30173.3 (3)
N2—Ho—N1—C4210.8 (2)N1—Ho—O12—C30149.2 (3)
C10—Ho—N1—C4282.9 (2)C10—Ho—O12—C30100.1 (3)
C20—Ho—N1—C4293.1 (2)C20—Ho—O12—C3082.1 (3)
Hoi—Ho—N1—C42134.35 (19)Hoi—Ho—O12—C3017.5 (3)
O8i—Ho—N2—C4015.4 (3)O5—C12—C13—C14179.2 (3)
O11i—Ho—N2—C40166.0 (2)C17—C12—C13—C141.2 (5)
O12—Ho—N2—C4033.6 (3)C12—C13—C14—C152.8 (5)
O4—Ho—N2—C4098.6 (3)C12—C13—C14—C19173.3 (3)
O3—Ho—N2—C4045.5 (3)C13—C14—C15—C164.3 (5)
O7—Ho—N2—C40114.0 (3)C19—C14—C15—C16171.8 (3)
O8—Ho—N2—C4091.9 (3)C14—C15—C16—C171.7 (6)
N1—Ho—N2—C40176.0 (3)C15—C16—C17—O6177.6 (3)
C10—Ho—N2—C4072.8 (3)C15—C16—C17—C122.3 (5)
C20—Ho—N2—C40104.2 (3)C18—O6—C17—C1617.2 (5)
Hoi—Ho—N2—C4052.0 (3)C18—O6—C17—C12162.7 (3)
O8i—Ho—N2—C41170.87 (19)O5—C12—C17—C16176.6 (3)
O11i—Ho—N2—C4120.2 (3)C13—C12—C17—C163.8 (5)
O12—Ho—N2—C41140.1 (2)O5—C12—C17—O63.5 (4)
O4—Ho—N2—C4187.7 (2)C13—C12—C17—O6176.2 (3)
O3—Ho—N2—C41140.7 (2)C15—C14—C19—C20127.4 (4)
O7—Ho—N2—C4159.8 (2)C13—C14—C19—C2056.6 (5)
O8—Ho—N2—C4181.8 (2)Ho—O7—C20—O80.6 (3)
N1—Ho—N2—C4110.3 (2)Ho—O7—C20—C19179.3 (3)
C10—Ho—N2—C41113.5 (2)Hoi—O8—C20—O7151.9 (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—C19179.3 (2)
C1—O1—C2—C7172.3 (3)Hoi—O8—C20—Ho152.5 (5)
O8i—Ho—O3—C10101.02 (18)C14—C19—C20—O78.4 (5)
O11i—Ho—O3—C1039.8 (2)C14—C19—C20—O8171.5 (3)
O12—Ho—O3—C10179.55 (18)O8i—Ho—C20—O7169.38 (17)
O4—Ho—O3—C100.98 (17)O11i—Ho—C20—O7116.47 (18)
O7—Ho—O3—C10131.53 (18)O12—Ho—C20—O797.44 (18)
O8—Ho—O3—C10141.18 (16)O4—Ho—C20—O780.8 (3)
N2—Ho—O3—C1097.85 (18)O3—Ho—C20—O792.9 (2)
N1—Ho—O3—C1049.00 (19)O8—Ho—C20—O7179.4 (3)
C20—Ho—O3—C10175.93 (17)N2—Ho—C20—O722.65 (19)
Hoi—Ho—O3—C10117.85 (16)N1—Ho—C20—O740.21 (18)
O1—C2—C3—C4178.4 (3)Hoi—Ho—C20—O7172.7 (2)
C7—C2—C3—C40.0 (5)O8i—Ho—C20—O810.0 (2)
O8i—Ho—O4—C1073.18 (18)O11i—Ho—C20—O864.16 (16)
O11i—Ho—O4—C10148.94 (19)O12—Ho—C20—O881.94 (16)
O12—Ho—O4—C102.8 (2)O4—Ho—C20—O899.8 (2)
O3—Ho—O4—C100.96 (16)O3—Ho—C20—O886.5 (2)
O7—Ho—O4—C10129.84 (18)O7—Ho—C20—O8179.4 (3)
O8—Ho—O4—C10128.11 (18)N2—Ho—C20—O8156.73 (16)
N2—Ho—O4—C1068.64 (19)N1—Ho—C20—O8140.42 (17)
N1—Ho—O4—C10133.25 (19)Hoi—Ho—C20—O86.72 (14)
C20—Ho—O4—C10175.08 (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—C60.2 (5)C22—C23—C24—C250.1 (6)
C9—C4—C5—C6179.2 (3)C23—C24—C25—C260.8 (5)
C4—C5—C6—C70.7 (6)C23—C24—C25—C29179.8 (3)
O8i—Ho—O7—C2012.7 (2)C24—C25—C26—C270.3 (5)
O11i—Ho—O7—C2062.64 (18)C29—C25—C26—C27179.7 (3)
O12—Ho—O7—C2076.13 (18)O9—C22—C27—O101.0 (5)
O4—Ho—O7—C20139.07 (18)C23—C22—C27—O10179.2 (4)
O3—Ho—O7—C20124.53 (18)O9—C22—C27—C26179.8 (3)
O8—Ho—O7—C200.35 (16)C23—C22—C27—C261.6 (6)
N2—Ho—O7—C20157.12 (19)C28—O10—C27—C22173.4 (4)
N1—Ho—O7—C20135.5 (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—O10180.0 (3)
C8—O2—C7—C64.3 (6)C24—C25—C29—C3049.1 (4)
C8—O2—C7—C2174.9 (4)C26—C25—C29—C30131.4 (3)
C5—C6—C7—O2177.9 (4)Ho—O12—C30—O1124.1 (5)
C5—C6—C7—C21.3 (6)Ho—O12—C30—C29154.3 (2)
O1—C2—C7—O20.2 (5)Hoi—O11—C30—O1210.5 (5)
C3—C2—C7—O2178.3 (3)Hoi—O11—C30—C29167.9 (2)
O1—C2—C7—C6179.5 (3)C25—C29—C30—O12104.4 (3)
C3—C2—C7—C60.9 (5)C25—C29—C30—O1174.2 (4)
O8i—Ho—O8—C20169.7 (2)C42—N1—C31—C321.9 (5)
O11i—Ho—O8—C20110.00 (17)Ho—N1—C31—C32170.6 (3)
O12—Ho—O8—C2089.62 (17)N1—C31—C32—C332.3 (5)
O4—Ho—O8—C20131.60 (18)C31—C32—C33—C340.7 (5)
O3—Ho—O8—C20129.07 (17)C32—C33—C34—C420.9 (5)
O7—Ho—O8—C200.34 (16)C32—C33—C34—C35178.2 (3)
N2—Ho—O8—C2028.05 (19)C33—C34—C35—C36177.5 (4)
N1—Ho—O8—C2041.30 (18)C42—C34—C35—C363.4 (6)
C10—Ho—O8—C20170.7 (2)C34—C35—C36—C370.3 (6)
Hoi—Ho—O8—C20169.7 (2)C35—C36—C37—C38178.0 (4)
O8i—Ho—O8—Hoi0.0C35—C36—C37—C413.6 (6)
O11i—Ho—O8—Hoi80.31 (8)C41—C37—C38—C390.5 (5)
O12—Ho—O8—Hoi80.07 (8)C36—C37—C38—C39179.0 (4)
O4—Ho—O8—Hoi58.71 (15)C37—C38—C39—C402.9 (6)
O3—Ho—O8—Hoi40.63 (13)C41—N2—C40—C390.5 (5)
O7—Ho—O8—Hoi169.35 (12)Ho—N2—C40—C39173.3 (3)
N2—Ho—O8—Hoi141.64 (9)C38—C39—C40—N22.4 (6)
N1—Ho—O8—Hoi149.00 (8)C40—N2—C41—C373.0 (5)
C10—Ho—O8—Hoi1.0 (2)Ho—N2—C41—C37171.0 (2)
C20—Ho—O8—Hoi169.7 (2)C40—N2—C41—C42176.7 (3)
C3—C4—C9—C10105.6 (4)Ho—N2—C41—C429.4 (4)
C5—C4—C9—C1073.4 (4)C38—C37—C41—N22.4 (5)
Ho—O3—C10—O41.7 (3)C36—C37—C41—N2176.1 (3)
Ho—O3—C10—C9179.1 (3)C38—C37—C41—C42177.2 (3)
Ho—O4—C10—O31.8 (3)C36—C37—C41—C424.3 (5)
Ho—O4—C10—C9179.0 (2)C31—N1—C42—C340.1 (5)
C4—C9—C10—O37.7 (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—C4110.9 (4)
O11i—Ho—C10—O3147.05 (16)C33—C34—C42—N11.3 (5)
O12—Ho—C10—O30.45 (18)C35—C34—C42—N1177.9 (3)
O4—Ho—C10—O3178.3 (3)C33—C34—C42—C41178.3 (3)
O7—Ho—C10—O388.8 (2)C35—C34—C42—C412.6 (5)
O8—Ho—C10—O374.6 (3)N2—C41—C42—N11.3 (4)
N2—Ho—C10—O374.42 (18)C37—C41—C42—N1178.3 (3)
N1—Ho—C10—O3136.28 (17)N2—C41—C42—C34179.1 (3)
Hoi—Ho—C10—O373.89 (18)C37—C41—C42—C341.3 (5)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
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: (i) x+1, y+1, z; (ii) x, y1, z+1; (iii) x, y+1, z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula[Ho2(C10H11O4)6(C12H8N2)2]
Mr1861.40
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)12.3069 (2), 12.3789 (2), 14.6591 (2)
α, β, γ (°)91.020 (1), 103.547 (1), 115.477 (1)
V3)1942.03 (5)
Z1
Radiation typeMo Kα
µ (mm1)2.11
Crystal size (mm)0.30 × 0.16 × 0.05
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.676, 0.909
No. of measured, independent and
observed [I > 2σ(I)] reflections
31540, 8930, 7217
Rint0.048
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.068, 1.04
No. of reflections8930
No. of parameters514
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.92, 0.57

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C40—H40A···O30.932.522.972 (4)110
C8—H8A···O6i0.962.553.319 (5)138
C16—H16A···O4ii0.932.513.410 (4)162
C18—H18C···O4ii0.962.363.266 (4)156
C21—H21C···O10.962.833.291 (6)111
C21—H21C···O20.962.823.749 (6)162
C31—H31A···O11iii0.932.373.008 (4)126
C38—H38A···O7iv0.932.363.215 (4)153
Symmetry codes: (i) x, y1, z+1; (ii) x, y+1, z; (iii) x+1, y+1, z; (iv) x, y+1, z.
 

References

First citationBruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, X., Zhang, Z.-Y. & Song, H.-B. (2005). J. Mol. Struct. 751, 33–40.  Web of Science CSD CrossRef CAS Google Scholar
First citationLi, X. & Zou, Y.-Q. (2005). Z. Kristallogr. New Cryst. Struct. 220, 33–35.  CAS Google Scholar
First citationLiu, J.-F., Xu, X.-D., Li, H.-Q. & Zhao, G.-L. (2010). Acta Cryst. E66, m291.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Y.-F., Liu, J.-F. & Zhao, G.-L. (2010). Chin. J. Inorg. Chem. 26, 328–332.  CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 10| October 2010| Pages m1272-m1273
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds