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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1411.
Published online 2010 October 13. doi:  10.1107/S1600536810040298
PMCID: PMC3009341

Tetra­kis[μ-2-(3,4-dimeth­oxy­phen­yl)acetato]-κ3 O 1,O 1′:O 13 O 1:O 1,O 1′4 O 1:O 1′-bis­{[2-(3,4-dimeth­oxy­phen­yl)acetato-κ2 O 1,O 1′](1,10-phenanthroline-κ2 N,N′)erbium(III)}

Abstract

In the dimeric centrosymmetric title complex, [Er2(C10H11O4)6(C12H8N2)2], the ErIII ion is nine-coordinated by five 2-(3,4-dimeth­oxy­lphen­yl)acetic acid (DMPA) ligands via seven O atoms and two N atoms from a bis-chelating 1,10-phenanthroline (phen) ligand in a distorted tricapped trigonal-prismatic geometry. The DMPA ligands are coordinated to the ErIII ion in bis-chelate, bridging and bridging tridentate modes. Relatively weak intra­molecular C—H(...)O inter­actions reinforce the stability of the mol­ecular structure. Inter­molecular C—H(...)O inter­actions are also observed.

Related literature

For the properties of carb­oxy­lic metal–organic complexes, see: Aoki et al. (2004 [triangle]); Yao et al. (2008 [triangle]). For related structures, see: Xia et al. (2008 [triangle]); Liu et al. (2007 [triangle]); Li et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1411-scheme1.jpg

Experimental

Crystal data

  • [Er2(C10H11O4)6(C12H8N2)2]
  • M r = 1866.06
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1411-efi1.jpg
  • a = 12.3101 (1) Å
  • b = 12.3646 (1) Å
  • c = 14.6260 (2) Å
  • α = 91.233 (1)°
  • β = 103.469 (1)°
  • γ = 114.876 (1)°
  • V = 1946.02 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 2.22 mm−1
  • T = 296 K
  • 0.60 × 0.23 × 0.17 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.547, T max = 0.681
  • 31446 measured reflections
  • 9031 independent reflections
  • 7784 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.059
  • S = 1.00
  • 9031 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.86 e Å−3
  • Δρmin = −0.46 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/S1600536810040298/pv2331sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040298/pv2331Isup2.hkl

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

supplementary crystallographic information

Comment

Interest in the design and synthesis of carboxylic metal-organic complexes has been increasing for decades owing to their potential practical applications, such as fluorescence (Aoki et al., 2004), magnetism (Yao et al., 2008). In this paper, we report the preparation and crystal structure of a new erbiumIII complex with the ligands 3,4-dimethoxylphenyl acetic acid (DMPA) (homoveratric acid) and 1,10-phenanthroline (phen). The crystal structures of several rare earth elements closely related to the title compound have been reported recently (Xia et al., 2008; Liu et al., 2007).

The title compound is a dimeric complex which consists of two central erbiumIII atoms coordinated with six 3,4-dimethoxylphenyl acetate ions and two phen molecules. The DMPA ligands are coordinated by three modes, bis-chelate, bridging and bridging tridentate. Each erbium atom is nine coordinated, seven O atoms from five DMPA molecules and two N atoms from a phen molecule (Fig. 1). The erbiumIII atom is in a distorted capped square prism environment. The Er—O bond lengths lie in the range 2.3006 (15)– 2.5020 (18) Å while the Er—N distances lie in the range 2.5135 (19)–2.588 (2) Å. There are no classical hydrogen bonds in the crystal structure. The most significant intermolecular interactions are C—H···O hydrogen bonds which lend stability to the structure (Table 1).

Experimental

All reagents and solvents used were of commercially available quality and wre not purified before using. The title compound was obtained by adding Er2O3 (0.5 mmol), homoveratric acid (3.0 mmol) and 1,10-phenanthroline (1.0 mmol) dissolved in 30 ml water, sealed in a 50 ml stainless steel reactor and kept at 433 K for three days. Then the reactor was cooled to room temperature at a speed of 5° per hour. The solution was filtered and the deposition was washed with ethanol to obtain pink block crystals of the title compound.

Refinement

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

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

[Er2(C10H11O4)6(C12H8N2)2]Z = 1
Mr = 1866.06F(000) = 942
Triclinic, P1Dx = 1.592 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3101 (1) ÅCell parameters from 9977 reflections
b = 12.3646 (1) Åθ = 1.8–27.6°
c = 14.6260 (2) ŵ = 2.22 mm1
α = 91.233 (1)°T = 296 K
β = 103.469 (1)°Block, pink
γ = 114.876 (1)°0.60 × 0.23 × 0.17 mm
V = 1946.02 (4) Å3

Data collection

Bruker APEXII area-detector diffractometer9031 independent reflections
Radiation source: fine-focus sealed tube7784 reflections with I > 2σ(I)
graphiteRint = 0.026
[var phi] and ω scansθmax = 27.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.547, Tmax = 0.681k = −16→16
31446 measured reflectionsl = −19→18

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)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0319P)2 + 0.6854P] where P = (Fo2 + 2Fc2)/3
9031 reflections(Δ/σ)max = 0.001
514 parametersΔρmax = 0.86 e Å3
0 restraintsΔρmin = −0.46 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
Er10.323792 (9)0.396219 (10)0.468848 (7)0.03886 (4)
C200.4065 (2)0.6372 (2)0.42582 (16)0.0393 (5)
O130.38701 (15)0.51937 (17)0.61236 (12)0.0457 (4)
O80.48695 (15)0.59812 (16)0.45693 (12)0.0446 (4)
C100.2382 (2)0.1683 (2)0.52142 (18)0.0428 (5)
O60.13086 (17)0.94341 (16)0.19422 (13)0.0499 (4)
O70.29483 (15)0.57170 (16)0.41590 (13)0.0478 (4)
O40.27956 (16)0.25477 (16)0.58501 (12)0.0459 (4)
O50.1108 (2)0.73691 (18)0.13200 (15)0.0657 (6)
C300.4893 (2)0.5821 (2)0.67136 (17)0.0434 (6)
N20.14185 (18)0.34244 (19)0.31818 (16)0.0452 (5)
O30.23958 (19)0.18490 (18)0.43671 (12)0.0537 (5)
C190.4540 (2)0.7642 (2)0.4028 (2)0.0539 (7)
H19A0.50250.81780.46170.065*
H19B0.51040.77360.36370.065*
O10.2656 (2)−0.0141 (3)0.93214 (16)0.0803 (7)
N10.11826 (19)0.3593 (2)0.49755 (16)0.0485 (5)
C310.1045 (3)0.3605 (3)0.5845 (2)0.0598 (7)
H31A0.17040.36820.63490.072*
C410.0342 (2)0.3398 (2)0.3297 (2)0.0440 (6)
C170.2058 (2)0.9018 (2)0.25119 (17)0.0391 (5)
C160.2857 (2)0.9600 (2)0.33756 (19)0.0495 (6)
H16A0.29001.03200.36240.059*
C120.1976 (2)0.7912 (2)0.21669 (17)0.0417 (5)
C240.5329 (2)0.5294 (3)0.83566 (18)0.0482 (6)
C140.3603 (2)0.8066 (2)0.35290 (19)0.0443 (6)
C50.2042 (3)0.0264 (2)0.64677 (19)0.0511 (6)
O90.7502 (3)0.5462 (3)1.0651 (2)0.0952 (9)
C130.2752 (2)0.7464 (2)0.26708 (18)0.0436 (5)
H13A0.27040.67380.24280.052*
O20.3979 (2)−0.0555 (2)0.83738 (18)0.0773 (6)
C70.3136 (3)−0.0197 (3)0.7876 (2)0.0548 (7)
C150.3609 (3)0.9109 (3)0.3883 (2)0.0558 (7)
H15A0.41290.94990.44790.067*
C400.1520 (3)0.3342 (2)0.2306 (2)0.0515 (6)
H40A0.22590.33750.22210.062*
C37−0.0644 (2)0.3288 (2)0.2518 (2)0.0549 (7)
O100.6576 (2)0.3197 (2)1.00775 (17)0.0818 (7)
C180.1621 (3)1.0676 (3)0.2155 (2)0.0599 (7)
H18A0.10491.08800.17130.090*
H18B0.24501.11550.21090.090*
H18C0.15751.08310.27880.090*
C280.6061 (4)0.1936 (4)0.9784 (3)0.0991 (14)
H28A0.64440.15791.02510.149*
H28B0.62110.17990.91870.149*
H28C0.51830.15810.97180.149*
C220.6623 (3)0.5063 (3)0.9784 (2)0.0626 (8)
C290.4884 (3)0.6070 (3)0.77314 (19)0.0533 (7)
H29A0.40480.59060.77520.064*
H29B0.54200.69120.79710.064*
C90.1860 (3)0.0392 (3)0.5431 (2)0.0598 (7)
H9A0.0977−0.00020.51190.072*
H9B0.2249−0.00260.51600.072*
C420.0212 (2)0.3471 (2)0.4237 (2)0.0470 (6)
C60.2942 (3)−0.0074 (2)0.6926 (2)0.0538 (7)
H6A0.3428−0.02210.65860.065*
C230.6219 (3)0.5780 (3)0.9218 (2)0.0564 (7)
H23A0.65510.66000.94210.068*
C390.0579 (3)0.3208 (3)0.1499 (2)0.0618 (7)
H39A0.06850.31310.08950.074*
C270.6132 (3)0.3837 (3)0.9484 (2)0.0598 (7)
C20.2414 (3)0.0033 (3)0.8388 (2)0.0550 (7)
C80.4842 (3)−0.0659 (4)0.7925 (3)0.0870 (11)
H8A0.5377−0.09190.83520.131*
H8B0.53320.01080.77570.131*
H8C0.4402−0.12370.73630.131*
C250.4838 (3)0.4076 (3)0.8068 (2)0.0585 (7)
H25A0.42370.37380.74930.070*
C30.1533 (3)0.0392 (3)0.7943 (2)0.0606 (7)
H3A0.10590.05580.82850.073*
C38−0.0498 (3)0.3191 (3)0.1611 (2)0.0635 (8)
H38A−0.11300.31160.10840.076*
C260.5234 (3)0.3349 (3)0.8629 (2)0.0641 (8)
H26A0.48920.25270.84280.077*
C33−0.1011 (3)0.3428 (3)0.5310 (3)0.0731 (10)
H33A−0.17380.33830.54290.088*
C36−0.1735 (3)0.3303 (3)0.2695 (3)0.0725 (10)
H36A−0.23680.32730.21870.087*
C40.1346 (3)0.0507 (3)0.6987 (2)0.0604 (7)
H4A0.07480.07510.66910.073*
C35−0.1856 (3)0.3360 (3)0.3573 (3)0.0763 (11)
H35A−0.25760.33670.36650.092*
C34−0.0903 (2)0.3413 (2)0.4383 (3)0.0599 (8)
C210.7933 (4)0.6639 (4)1.1050 (3)0.1027 (14)
H21A0.85410.67941.16440.154*
H21B0.72520.67671.11560.154*
H21C0.83030.71741.06280.154*
C32−0.0054 (3)0.3508 (3)0.6039 (3)0.0713 (9)
H32A−0.01270.34980.66570.086*
C110.0805 (4)0.6155 (3)0.1040 (3)0.0807 (11)
H11A0.02010.58780.04340.121*
H11B0.04680.56740.15020.121*
H11C0.15400.60880.09940.121*
C10.1893 (4)−0.0026 (4)0.9857 (3)0.0985 (13)
H1A0.2161−0.01681.04950.148*
H1B0.1048−0.06020.95780.148*
H1C0.19470.07720.98660.148*
O110.59453 (15)0.62444 (18)0.65483 (12)0.0506 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Er10.04056 (6)0.05999 (8)0.03747 (7)0.03744 (5)0.01798 (4)0.02142 (5)
C200.0433 (12)0.0584 (15)0.0339 (12)0.0370 (11)0.0129 (9)0.0172 (11)
O130.0462 (9)0.0663 (11)0.0440 (10)0.0377 (9)0.0209 (8)0.0172 (8)
O80.0462 (9)0.0686 (11)0.0445 (9)0.0443 (9)0.0194 (7)0.0268 (8)
C100.0418 (12)0.0574 (16)0.0415 (14)0.0314 (11)0.0134 (10)0.0163 (12)
O60.0578 (10)0.0528 (11)0.0477 (10)0.0380 (9)0.0026 (8)0.0126 (8)
O70.0417 (9)0.0594 (11)0.0595 (11)0.0357 (8)0.0169 (8)0.0236 (9)
O40.0544 (10)0.0561 (11)0.0413 (10)0.0338 (8)0.0191 (8)0.0156 (9)
O50.0816 (14)0.0508 (12)0.0545 (12)0.0366 (11)−0.0147 (10)−0.0007 (9)
C300.0524 (14)0.0620 (16)0.0395 (13)0.0423 (13)0.0207 (11)0.0212 (12)
N20.0429 (10)0.0523 (12)0.0533 (13)0.0318 (10)0.0141 (9)0.0193 (10)
O30.0765 (12)0.0665 (12)0.0352 (10)0.0444 (10)0.0195 (9)0.0196 (9)
C190.0426 (13)0.0563 (16)0.0697 (19)0.0326 (12)0.0052 (12)0.0174 (14)
O10.0925 (16)0.115 (2)0.0494 (13)0.0544 (15)0.0284 (11)0.0366 (13)
N10.0455 (11)0.0597 (13)0.0610 (14)0.0348 (10)0.0279 (10)0.0220 (11)
C310.0591 (16)0.075 (2)0.071 (2)0.0411 (15)0.0392 (15)0.0243 (16)
C410.0361 (11)0.0365 (12)0.0649 (17)0.0228 (10)0.0096 (11)0.0134 (11)
C170.0422 (11)0.0470 (13)0.0396 (13)0.0293 (10)0.0119 (10)0.0158 (10)
C160.0559 (14)0.0527 (15)0.0485 (15)0.0365 (13)0.0048 (11)0.0030 (12)
C120.0458 (12)0.0441 (13)0.0402 (13)0.0249 (11)0.0099 (10)0.0118 (11)
C240.0515 (13)0.0699 (18)0.0362 (13)0.0335 (13)0.0210 (11)0.0172 (12)
C140.0404 (12)0.0483 (14)0.0510 (15)0.0272 (11)0.0084 (10)0.0180 (12)
C50.0611 (15)0.0474 (15)0.0462 (15)0.0217 (12)0.0202 (12)0.0161 (12)
O90.0987 (19)0.0903 (19)0.0764 (17)0.0460 (16)−0.0207 (14)−0.0072 (15)
C130.0495 (13)0.0421 (13)0.0488 (14)0.0284 (11)0.0139 (11)0.0148 (11)
O20.0752 (14)0.0984 (17)0.0823 (16)0.0546 (13)0.0297 (12)0.0420 (14)
C70.0564 (15)0.0543 (16)0.0589 (17)0.0259 (13)0.0202 (13)0.0225 (13)
C150.0576 (15)0.0608 (17)0.0488 (16)0.0372 (14)−0.0076 (12)0.0003 (13)
C400.0538 (14)0.0599 (17)0.0509 (16)0.0355 (13)0.0106 (12)0.0177 (13)
C370.0392 (12)0.0402 (14)0.080 (2)0.0204 (11)0.0007 (13)0.0076 (13)
O100.0985 (18)0.0833 (17)0.0658 (15)0.0521 (14)0.0009 (12)0.0231 (12)
C180.0777 (19)0.0581 (17)0.0593 (18)0.0479 (16)0.0101 (14)0.0155 (14)
C280.119 (3)0.083 (3)0.095 (3)0.050 (3)0.012 (3)0.040 (2)
C220.0589 (16)0.079 (2)0.0508 (17)0.0343 (16)0.0077 (13)0.0156 (15)
C290.0659 (16)0.0726 (18)0.0462 (15)0.0471 (15)0.0265 (13)0.0179 (13)
C90.0725 (18)0.0563 (17)0.0470 (16)0.0248 (14)0.0158 (14)0.0124 (13)
C420.0362 (11)0.0379 (13)0.0766 (19)0.0222 (10)0.0205 (12)0.0140 (12)
C60.0624 (16)0.0504 (15)0.0588 (17)0.0268 (13)0.0293 (13)0.0198 (13)
C230.0593 (16)0.0619 (18)0.0491 (16)0.0279 (14)0.0140 (13)0.0061 (13)
C390.0675 (18)0.0643 (19)0.0539 (17)0.0357 (15)0.0030 (14)0.0139 (14)
C270.0652 (17)0.074 (2)0.0461 (16)0.0363 (16)0.0123 (13)0.0196 (14)
C20.0620 (16)0.0591 (17)0.0479 (16)0.0260 (14)0.0217 (13)0.0218 (13)
C80.070 (2)0.096 (3)0.115 (3)0.051 (2)0.030 (2)0.028 (2)
C250.0655 (17)0.0656 (19)0.0435 (15)0.0305 (15)0.0091 (13)0.0111 (14)
C30.0681 (18)0.074 (2)0.0573 (18)0.0394 (16)0.0315 (14)0.0205 (15)
C380.0523 (15)0.0535 (17)0.074 (2)0.0259 (13)−0.0080 (14)0.0107 (15)
C260.077 (2)0.0621 (19)0.0504 (17)0.0314 (16)0.0094 (14)0.0122 (14)
C330.0485 (16)0.0600 (19)0.129 (3)0.0275 (14)0.0486 (19)0.0112 (19)
C360.0358 (13)0.0618 (19)0.112 (3)0.0264 (13)−0.0030 (16)−0.0045 (19)
C40.0664 (17)0.073 (2)0.0565 (18)0.0415 (16)0.0197 (14)0.0242 (15)
C350.0327 (13)0.0607 (19)0.135 (4)0.0248 (13)0.0141 (17)−0.003 (2)
C340.0391 (13)0.0462 (15)0.104 (3)0.0224 (11)0.0286 (15)0.0094 (15)
C210.090 (3)0.121 (4)0.071 (3)0.040 (3)−0.010 (2)−0.024 (2)
C320.073 (2)0.075 (2)0.094 (3)0.0404 (17)0.057 (2)0.0218 (18)
C110.096 (3)0.0539 (19)0.077 (2)0.0381 (18)−0.0111 (19)−0.0072 (17)
C10.134 (4)0.129 (4)0.055 (2)0.066 (3)0.046 (2)0.028 (2)
O110.0455 (9)0.0815 (13)0.0406 (10)0.0387 (9)0.0181 (7)0.0174 (9)

Geometric parameters (Å, °)

Er1—O8i2.3006 (15)C7—C61.376 (4)
Er1—O11i2.3220 (16)C7—C21.395 (4)
Er1—O132.3313 (18)C15—H15A0.9300
Er1—O32.359 (2)C40—C391.399 (4)
Er1—O42.4494 (17)C40—H40A0.9300
Er1—O72.4554 (16)C37—C381.388 (5)
Er1—O82.5020 (18)C37—C361.432 (4)
Er1—N12.5135 (19)O10—C271.361 (4)
Er1—N22.588 (2)O10—C281.425 (5)
Er1—C102.760 (3)C18—H18A0.9600
Er1—C202.853 (2)C18—H18B0.9600
Er1—Er1i3.8637 (2)C18—H18C0.9600
C20—O71.238 (3)C28—H28A0.9600
C20—O81.275 (3)C28—H28B0.9600
C20—C191.504 (4)C28—H28C0.9600
O13—C301.255 (3)C22—C231.389 (4)
O8—Er1i2.3006 (15)C22—C271.390 (5)
C10—O41.243 (3)C29—H29A0.9700
C10—O31.263 (3)C29—H29B0.9700
C10—C91.521 (4)C9—H9A0.9700
O6—C171.367 (3)C9—H9B0.9700
O6—C181.425 (3)C42—C341.409 (3)
O5—C121.368 (3)C6—H6A0.9300
O5—C111.411 (4)C23—H23A0.9300
C30—O111.261 (3)C39—C381.366 (4)
C30—C291.517 (3)C39—H39A0.9300
N2—C401.322 (3)C27—C261.382 (4)
N2—C411.362 (3)C2—C31.374 (4)
C19—C141.507 (3)C8—H8A0.9600
C19—H19A0.9700C8—H8B0.9600
C19—H19B0.9700C8—H8C0.9600
O1—C21.370 (3)C25—C261.391 (4)
O1—C11.404 (4)C25—H25A0.9300
N1—C311.322 (4)C3—C41.384 (4)
N1—C421.363 (3)C3—H3A0.9300
C31—C321.402 (4)C38—H38A0.9300
C31—H31A0.9300C26—H26A0.9300
C41—C371.414 (4)C33—C321.359 (5)
C41—C421.427 (4)C33—C341.394 (5)
C17—C161.367 (4)C33—H33A0.9300
C17—C121.402 (3)C36—C351.331 (5)
C16—C151.395 (3)C36—H36A0.9300
C16—H16A0.9300C4—H4A0.9300
C12—C131.378 (3)C35—C341.439 (5)
C24—C251.378 (4)C35—H35A0.9300
C24—C231.386 (4)C21—H21A0.9600
C24—C291.518 (4)C21—H21B0.9600
C14—C131.385 (4)C21—H21C0.9600
C14—C151.376 (4)C32—H32A0.9300
C5—C61.381 (4)C11—H11A0.9600
C5—C41.382 (4)C11—H11B0.9600
C5—C91.502 (4)C11—H11C0.9600
O9—C221.381 (4)C1—H1A0.9600
O9—C211.382 (5)C1—H1B0.9600
C13—H13A0.9300C1—H1C0.9600
O2—C71.360 (3)O11—Er1i2.3220 (16)
O2—C81.418 (4)
O8i—Er1—O11i75.72 (6)C15—C14—C19121.1 (2)
O8i—Er1—O1375.88 (6)C6—C5—C4118.7 (3)
O11i—Er1—O13138.54 (6)C6—C5—C9119.9 (3)
O8i—Er1—O389.35 (6)C4—C5—C9121.4 (3)
O11i—Er1—O379.07 (7)C22—O9—C21118.5 (3)
O13—Er1—O3129.90 (6)C12—C13—C14121.6 (2)
O8i—Er1—O475.22 (6)C12—C13—H13A119.2
O11i—Er1—O4123.98 (6)C14—C13—H13A119.2
O13—Er1—O475.99 (6)C7—O2—C8118.1 (3)
O3—Er1—O453.92 (6)O2—C7—C6125.2 (3)
O8i—Er1—O7124.19 (6)O2—C7—C2115.6 (3)
O11i—Er1—O793.59 (6)C6—C7—C2119.2 (3)
O13—Er1—O778.30 (6)C14—C15—C16122.0 (2)
O3—Er1—O7143.05 (6)C14—C15—H15A119.0
O4—Er1—O7142.12 (6)C16—C15—H15A119.0
O8i—Er1—O872.95 (6)N2—C40—C39123.6 (3)
O11i—Er1—O871.53 (6)N2—C40—H40A118.2
O13—Er1—O871.64 (6)C39—C40—H40A118.2
O3—Er1—O8148.53 (6)C38—C37—C41118.1 (3)
O4—Er1—O8138.95 (6)C38—C37—C36122.9 (3)
O7—Er1—O852.09 (5)C41—C37—C36119.0 (3)
O8i—Er1—N1141.53 (7)C27—O10—C28116.6 (3)
O11i—Er1—N1139.61 (7)O6—C18—H18A109.5
O13—Er1—N178.63 (7)O6—C18—H18B109.5
O3—Er1—N185.34 (7)H18A—C18—H18B109.5
O4—Er1—N170.95 (6)O6—C18—H18C109.5
O7—Er1—N177.09 (6)H18A—C18—H18C109.5
O8—Er1—N1124.64 (6)H18B—C18—H18C109.5
O8i—Er1—N2150.03 (6)O10—C28—H28A109.5
O11i—Er1—N275.75 (6)O10—C28—H28B109.5
O13—Er1—N2133.22 (6)H28A—C28—H28B109.5
O3—Er1—N276.40 (6)O10—C28—H28C109.5
O4—Er1—N2114.34 (6)H28A—C28—H28C109.5
O7—Er1—N266.72 (6)H28B—C28—H28C109.5
O8—Er1—N2106.18 (6)O9—C22—C23125.4 (3)
N1—Er1—N264.39 (7)O9—C22—C27114.9 (3)
O8i—Er1—C1081.95 (6)C23—C22—C27119.7 (3)
O11i—Er1—C10102.45 (7)C30—C29—C24110.9 (2)
O13—Er1—C10102.77 (7)C30—C29—H29A109.5
O3—Er1—C1027.15 (7)C24—C29—H29A109.5
O4—Er1—C1026.78 (7)C30—C29—H29B109.5
O7—Er1—C10152.38 (6)C24—C29—H29B109.5
O8—Er1—C10154.90 (6)H29A—C29—H29B108.1
N1—Er1—C1076.13 (7)C5—C9—C10114.9 (2)
N2—Er1—C1095.40 (7)C5—C9—H9A108.5
O8i—Er1—C2099.10 (6)C10—C9—H9A108.5
O11i—Er1—C2081.86 (7)C5—C9—H9B108.5
O13—Er1—C2073.55 (6)C10—C9—H9B108.5
O3—Er1—C20156.53 (6)H9A—C9—H9B107.5
O4—Er1—C20149.47 (7)N1—C42—C34121.8 (3)
O7—Er1—C2025.58 (6)N1—C42—C41118.3 (2)
O8—Er1—C2026.51 (5)C34—C42—C41119.9 (3)
N1—Er1—C20100.73 (6)C5—C6—C7121.5 (3)
N2—Er1—C2085.77 (6)C5—C6—H6A119.3
C10—Er1—C20175.69 (7)C7—C6—H6A119.3
O8i—Er1—Er1i38.25 (4)C22—C23—C24121.1 (3)
O11i—Er1—Er1i69.39 (5)C22—C23—H23A119.4
O13—Er1—Er1i69.56 (4)C24—C23—H23A119.4
O3—Er1—Er1i123.06 (5)C38—C39—C40118.9 (3)
O4—Er1—Er1i109.66 (4)C38—C39—H39A120.6
O7—Er1—Er1i86.38 (4)C40—C39—H39A120.6
O8—Er1—Er1i34.70 (3)O10—C27—C22116.1 (3)
N1—Er1—Er1i146.54 (5)O10—C27—C26124.6 (3)
N2—Er1—Er1i134.13 (5)C22—C27—C26119.3 (3)
C10—Er1—Er1i120.20 (5)O1—C2—C3125.3 (3)
C20—Er1—Er1i60.97 (4)O1—C2—C7114.9 (3)
O7—C20—O8120.1 (2)C3—C2—C7119.7 (3)
O7—C20—C19122.8 (2)O2—C8—H8A109.5
O8—C20—C19117.0 (2)O2—C8—H8B109.5
O7—C20—Er158.95 (12)H8A—C8—H8B109.5
O8—C20—Er161.19 (13)O2—C8—H8C109.5
C19—C20—Er1178.08 (16)H8A—C8—H8C109.5
C30—O13—Er1135.18 (14)H8B—C8—H8C109.5
C20—O8—Er1i158.37 (18)C24—C25—C26120.6 (3)
C20—O8—Er192.29 (14)C24—C25—H25A119.7
Er1i—O8—Er1107.05 (6)C26—C25—H25A119.7
O4—C10—O3121.0 (2)C2—C3—C4120.3 (3)
O4—C10—C9121.2 (2)C2—C3—H3A119.9
O3—C10—C9117.8 (2)C4—C3—H3A119.9
O4—C10—Er162.56 (13)C39—C38—C37119.6 (3)
O3—C10—Er158.45 (13)C39—C38—H38A120.2
C9—C10—Er1175.98 (19)C37—C38—H38A120.2
C17—O6—C18116.0 (2)C25—C26—C27120.5 (3)
C20—O7—Er195.47 (13)C25—C26—H26A119.7
C10—O4—Er190.66 (14)C27—C26—H26A119.7
C12—O5—C11117.0 (2)C32—C33—C34119.9 (3)
O13—C30—O11126.2 (2)C32—C33—H33A120.1
O13—C30—C29117.7 (2)C34—C33—H33A120.1
O11—C30—C29116.2 (2)C35—C36—C37121.1 (3)
C40—N2—C41117.6 (2)C35—C36—H36A119.4
C40—N2—Er1124.18 (16)C37—C36—H36A119.4
C41—N2—Er1117.48 (17)C3—C4—C5120.5 (3)
C10—O3—Er194.40 (16)C3—C4—H4A119.7
C14—C19—C20118.0 (2)C5—C4—H4A119.7
C14—C19—H19A107.8C36—C35—C34121.7 (3)
C20—C19—H19A107.8C36—C35—H35A119.1
C14—C19—H19B107.8C34—C35—H35A119.1
C20—C19—H19B107.8C33—C34—C42117.9 (3)
H19A—C19—H19B107.1C33—C34—C35123.6 (3)
C2—O1—C1117.9 (3)C42—C34—C35118.5 (3)
C31—N1—C42118.5 (2)O9—C21—H21A109.5
C31—N1—Er1121.14 (18)O9—C21—H21B109.5
C42—N1—Er1120.17 (16)H21A—C21—H21B109.5
N1—C31—C32122.7 (3)O9—C21—H21C109.5
N1—C31—H31A118.6H21A—C21—H21C109.5
C32—C31—H31A118.6H21B—C21—H21C109.5
N2—C41—C37122.1 (3)C33—C32—C31119.1 (3)
N2—C41—C42118.3 (2)C33—C32—H32A120.4
C37—C41—C42119.6 (2)C31—C32—H32A120.4
O6—C17—C16124.7 (2)O5—C11—H11A109.5
O6—C17—C12116.2 (2)O5—C11—H11B109.5
C16—C17—C12119.1 (2)H11A—C11—H11B109.5
C17—C16—C15119.7 (2)O5—C11—H11C109.5
C17—C16—H16A120.1H11A—C11—H11C109.5
C15—C16—H16A120.1H11B—C11—H11C109.5
C13—C12—O5125.2 (2)O1—C1—H1A109.5
C13—C12—C17119.8 (2)O1—C1—H1B109.5
O5—C12—C17115.0 (2)H1A—C1—H1B109.5
C25—C24—C23118.8 (3)O1—C1—H1C109.5
C25—C24—C29119.6 (2)H1A—C1—H1C109.5
C23—C24—C29121.5 (3)H1B—C1—H1C109.5
C13—C14—C15117.4 (2)C30—O11—Er1i137.08 (17)
C13—C14—C19121.5 (2)
O8i—Er1—N1—C3115.8 (3)O8i—Er1—C10—O3−104.49 (15)
O11i—Er1—N1—C31166.0 (2)O11i—Er1—C10—O3−31.16 (15)
O13—Er1—N1—C31−33.4 (2)O13—Er1—C10—O3−177.93 (14)
O3—Er1—N1—C3198.9 (2)O4—Er1—C10—O3−177.6 (2)
O4—Er1—N1—C3145.5 (2)O7—Er1—C10—O392.9 (2)
O7—Er1—N1—C31−113.9 (2)O8—Er1—C10—O3−104.1 (2)
O8—Er1—N1—C31−91.4 (2)N1—Er1—C10—O3107.35 (16)
N2—Er1—N1—C31176.0 (2)N2—Er1—C10—O345.44 (15)
C10—Er1—N1—C3172.9 (2)Er1i—Er1—C10—O3−104.38 (14)
C20—Er1—N1—C31−104.0 (2)C11—O5—C12—C1313.9 (4)
Er1i—Er1—N1—C31−51.5 (3)C11—O5—C12—C17−167.2 (3)
O8i—Er1—N1—C42−169.36 (16)O8i—Er1—O13—C3022.5 (2)
O11i—Er1—N1—C42−19.2 (2)O11i—Er1—O13—C30−25.5 (3)
O13—Er1—N1—C42141.41 (19)O3—Er1—O13—C3099.4 (2)
O3—Er1—N1—C42−86.30 (19)O4—Er1—O13—C30100.5 (2)
O4—Er1—N1—C42−139.6 (2)O7—Er1—O13—C30−107.6 (2)
O7—Er1—N1—C4260.95 (18)O8—Er1—O13—C30−53.9 (2)
O8—Er1—N1—C4283.4 (2)N1—Er1—O13—C30173.4 (2)
N2—Er1—N1—C42−9.14 (17)N2—Er1—O13—C30−149.1 (2)
C10—Er1—N1—C42−112.2 (2)C10—Er1—O13—C30100.7 (2)
C20—Er1—N1—C4270.81 (19)C20—Er1—O13—C30−81.7 (2)
Er1i—Er1—N1—C42123.31 (17)Er1i—Er1—O13—C30−17.1 (2)
O8i—Er1—N2—C40−25.0 (3)O5—C12—C13—C14−179.6 (3)
O11i—Er1—N2—C40−6.8 (2)C17—C12—C13—C141.5 (4)
O13—Er1—N2—C40138.47 (19)C12—C13—C14—C152.8 (4)
O3—Er1—N2—C40−88.8 (2)C12—C13—C14—C19−173.6 (2)
O4—Er1—N2—C40−128.0 (2)C13—C14—C15—C16−4.6 (4)
O7—Er1—N2—C4093.5 (2)C19—C14—C15—C16171.8 (3)
O8—Er1—N2—C4058.7 (2)C14—C15—C16—C172.1 (5)
N1—Er1—N2—C40179.9 (2)C15—C16—C17—O6−177.9 (3)
C10—Er1—N2—C40−108.3 (2)C15—C16—C17—C122.4 (4)
C20—Er1—N2—C4075.9 (2)C18—O6—C17—C1616.8 (4)
Er1i—Er1—N2—C4034.4 (2)C18—O6—C17—C12−163.5 (2)
O8i—Er1—N2—C41164.83 (15)O5—C12—C17—C16176.9 (2)
O11i—Er1—N2—C41−176.94 (18)C13—C12—C17—C16−4.1 (4)
O13—Er1—N2—C41−31.7 (2)O5—C12—C17—O6−2.8 (3)
O3—Er1—N2—C41101.10 (18)C13—C12—C17—O6176.2 (2)
O4—Er1—N2—C4161.84 (18)C15—C14—C19—C20127.5 (3)
O7—Er1—N2—C41−76.61 (17)C13—C14—C19—C20−56.2 (4)
O8—Er1—N2—C41−111.39 (17)Er1—O7—C20—O8−1.0 (2)
N1—Er1—N2—C419.76 (16)Er1—O7—C20—C19179.2 (2)
C10—Er1—N2—C4181.55 (18)Er1i—O8—C20—O7−153.0 (3)
C20—Er1—N2—C41−94.28 (17)Er1—O8—C20—O71.0 (2)
Er1i—Er1—N2—C41−135.71 (15)Er1i—O8—C20—C1926.8 (6)
C1—O1—C2—C34.7 (5)Er1—O8—C20—C19−179.2 (2)
C1—O1—C2—C7−174.7 (3)Er1i—O8—C20—Er1−154.0 (4)
O8i—Er1—O3—C1073.48 (15)C14—C19—C20—O7−8.8 (4)
O11i—Er1—O3—C10149.04 (15)C14—C19—C20—O8171.4 (2)
O13—Er1—O3—C102.63 (18)O8i—Er1—C20—O7−169.60 (15)
O4—Er1—O3—C101.36 (13)O11i—Er1—C20—O7116.40 (15)
O7—Er1—O3—C10−129.64 (15)O13—Er1—C20—O7−97.38 (15)
O8—Er1—O3—C10127.95 (15)O3—Er1—C20—O780.5 (2)
N1—Er1—O3—C10−68.39 (15)O4—Er1—C20—O7−93.27 (18)
N2—Er1—O3—C10−133.14 (16)O8—Er1—C20—O7−179.0 (2)
C20—Er1—O3—C10−174.74 (15)N1—Er1—C20—O7−22.72 (16)
Er1i—Er1—O3—C1092.64 (14)N2—Er1—C20—O740.19 (15)
O1—C2—C3—C4−178.3 (3)Er1i—Er1—C20—O7−172.71 (17)
C7—C2—C3—C41.1 (5)O8i—Er1—C20—O89.44 (17)
O8i—Er1—O4—C10−101.61 (14)O11i—Er1—C20—O8−64.56 (14)
O11i—Er1—O4—C10−40.67 (16)O13—Er1—C20—O881.66 (14)
O13—Er1—O4—C10179.62 (14)O3—Er1—C20—O8−100.4 (2)
O3—Er1—O4—C10−1.38 (13)O4—Er1—C20—O885.76 (18)
O7—Er1—O4—C10130.94 (14)O7—Er1—C20—O8179.0 (2)
O8—Er1—O4—C10−141.74 (13)N1—Er1—C20—O8156.31 (14)
N1—Er1—O4—C1096.99 (15)N2—Er1—C20—O8−140.77 (14)
N2—Er1—O4—C1048.17 (15)Er1i—Er1—C20—O86.33 (12)
C20—Er1—O4—C10175.56 (13)C21—O9—C22—C237.2 (6)
Er1i—Er1—O4—C10−118.54 (13)C21—O9—C22—C27−172.6 (4)
C2—C3—C4—C50.0 (5)O9—C22—C23—C24−179.8 (3)
C3—C4—C5—C6−1.2 (5)C27—C22—C23—C24−0.1 (5)
C3—C4—C5—C9−179.5 (3)C22—C23—C24—C250.5 (4)
C4—C5—C6—C71.5 (4)C22—C23—C24—C29−179.7 (3)
C9—C5—C6—C7179.8 (3)C23—C24—C25—C26−0.4 (4)
O8i—Er1—O7—C2012.45 (18)C29—C24—C25—C26179.9 (3)
O11i—Er1—O7—C20−62.67 (16)C24—C25—C26—C27−0.3 (5)
O13—Er1—O7—C2076.21 (15)C28—O10—C27—C26−0.4 (5)
O3—Er1—O7—C20−139.21 (15)C28—O10—C27—C22178.9 (3)
O4—Er1—O7—C20124.29 (15)C25—C26—C27—O10−180.0 (3)
O8—Er1—O7—C200.55 (14)C25—C26—C27—C220.8 (5)
N1—Er1—O7—C20157.08 (16)O9—C22—C27—O10−0.1 (4)
N2—Er1—O7—C20−135.51 (17)C23—C22—C27—O10−179.9 (3)
C10—Er1—O7—C20171.48 (16)O9—C22—C27—C26179.2 (3)
Er1i—Er1—O7—C206.38 (15)C23—C22—C27—C26−0.6 (5)
C8—O2—C7—C68.8 (5)C25—C24—C29—C30−48.6 (3)
C8—O2—C7—C2−172.4 (3)C23—C24—C29—C30131.7 (3)
C5—C6—C7—O2178.3 (3)Er1—O13—C30—O1123.2 (4)
C5—C6—C7—C2−0.5 (4)Er1—O13—C30—C29−154.82 (18)
C3—C2—C7—O2−179.7 (3)Er1i—O11—C30—O13−9.5 (4)
O1—C2—C7—O2−0.3 (4)Er1i—O11—C30—C29168.52 (17)
C3—C2—C7—C6−0.8 (4)C24—C29—C30—O13103.7 (3)
O1—C2—C7—C6178.6 (3)C24—C29—C30—O11−74.5 (3)
O8i—Er1—O8—C20−170.25 (18)C42—N1—C31—C32−0.7 (4)
O11i—Er1—O8—C20109.53 (15)Er1—N1—C31—C32174.2 (2)
O13—Er1—O8—C20−89.87 (14)N1—C31—C32—C33−1.5 (5)
O3—Er1—O8—C20131.40 (15)C31—C32—C33—C341.4 (5)
O4—Er1—O8—C20−129.55 (14)C32—C33—C34—C420.7 (5)
O7—Er1—O8—C20−0.53 (13)C32—C33—C34—C35−178.3 (3)
N1—Er1—O8—C20−28.67 (17)C33—C34—C35—C36−177.5 (3)
N2—Er1—O8—C2041.05 (15)C42—C34—C35—C363.5 (5)
C10—Er1—O8—C20−170.62 (16)C34—C35—C36—C370.2 (5)
Er1i—Er1—O8—C20−170.25 (18)C35—C36—C37—C38177.9 (3)
O8i—Er1—O8—Er1i0.0C35—C36—C37—C41−3.3 (5)
O11i—Er1—O8—Er1i−80.22 (7)C41—C37—C38—C39−0.2 (4)
O13—Er1—O8—Er1i80.38 (7)C36—C37—C38—C39178.6 (3)
O3—Er1—O8—Er1i−58.36 (14)C37—C38—C39—C40−1.0 (4)
O4—Er1—O8—Er1i40.69 (11)C41—N2—C40—C39−1.1 (4)
O7—Er1—O8—Er1i169.72 (11)Er1—N2—C40—C39−171.2 (2)
N1—Er1—O8—Er1i141.58 (8)C38—C39—C40—N21.7 (5)
N2—Er1—O8—Er1i−148.70 (7)C40—N2—C41—C37−0.1 (4)
C10—Er1—O8—Er1i−0.4 (2)Er1—N2—C41—C37170.66 (18)
C20—Er1—O8—Er1i170.25 (18)C40—N2—C41—C42179.2 (2)
C6—C5—C9—C10−104.0 (3)Er1—N2—C41—C42−10.0 (3)
C4—C5—C9—C1074.2 (4)C38—C37—C41—N20.8 (4)
Er1—O4—C10—O32.4 (2)C36—C37—C41—N2−178.1 (3)
Er1—O4—C10—C9−178.5 (2)C38—C37—C41—C42−178.5 (2)
Er1—O3—C10—O4−2.5 (2)C36—C37—C41—C422.6 (4)
Er1—O3—C10—C9178.3 (2)C31—N1—C42—C343.0 (4)
C5—C9—C10—O4−7.7 (4)Er1—N1—C42—C34−171.98 (19)
C5—C9—C10—O3171.4 (3)C31—N1—C42—C41−176.9 (2)
O8i—Er1—C10—O473.06 (14)Er1—N1—C42—C418.1 (3)
O11i—Er1—C10—O4146.40 (13)C33—C34—C42—N1−3.0 (4)
O13—Er1—C10—O4−0.38 (14)C35—C34—C42—N1176.1 (3)
O3—Er1—C10—O4177.6 (2)C33—C34—C42—C41176.9 (3)
O7—Er1—C10—O4−89.5 (2)C35—C34—C42—C41−4.0 (4)
O8—Er1—C10—O473.4 (2)N2—C41—C42—N11.6 (3)
N1—Er1—C10—O4−75.10 (14)C37—C41—C42—N1−179.1 (2)
N2—Er1—C10—O4−137.01 (14)N2—C41—C42—C34−178.3 (2)
Er1i—Er1—C10—O473.17 (14)C37—C41—C42—C341.0 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···O6ii0.962.543.312 (4)137
C16—H16A···O3iii0.932.523.421 (3)163
C18—H18C···O3iii0.962.383.267 (4)153
C25—H25A···O40.932.603.515 (3)169
C28—H28A···O1iv0.962.483.353 (6)151
C28—H28A···O2iv0.962.443.220 (5)138
C33—H33A···O7v0.932.373.218 (3)152
C31—H31A···O40.932.512.953 (3)109
C40—H40A···O11i0.932.362.998 (4)125

Symmetry codes: (ii) x, y−1, z+1; (iii) x, y+1, z; (iv) −x+1, −y, −z+2; (v) −x, −y+1, −z+1; (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2331).

References

  • Aoki, S., Kagata, D. & Shiro, M. (2004). J. Am. Chem. Soc.126, 13377–13390. [PubMed]
  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. [PMC free article] [PubMed]
  • Liu, Y.-F., Xia, H.-T., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m2608–m2609.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xia, H.-T., Liu, Y.-F., Chen, L. & Wang, D.-Q. (2008). Acta Cryst. E64, m1419–m1420. [PMC free article] [PubMed]
  • Yao, Y.-L., Che, Y.-X. & Zheng, J.-M. (2008). Cryst. Growth. Des.8, 2299–2306.

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