PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 October 1; 66(Pt 10): m1332–m1333.
Published online 2010 September 30. doi:  10.1107/S1600536810038109
PMCID: PMC2983206

(Methanol-κO)bis­{2-meth­oxy-6-[(4-methyl­phen­yl)iminiometh­yl]phenolato-κ2 O,O′}tris­(nitrato-κ2 O,O′)lanthanum(III)

Abstract

The asymmetric unit of title compound, [La(NO3)3(C15H15NO2)2(CH3OH)], consists of two Schiff base 2-meth­oxy-6-[(4-methyl­phen­yl)iminiometh­yl]phenolato (HL) ligands, three independent nitrate anions and one methanol mol­ecule coordinated to LaIII. The coordination environment of the LaIII ion is formed by eleven O atoms. Three bidentate nitrate anions coordinate to the LaIII ion, while two HL ligands chelate the metal center with O atoms from the phenolate and meth­oxy groups. The HL ligands are zwitterionic, with protonated imine N atoms. The coordination sphere is completed by one methanol mol­ecule. The protonated imine N atoms are involved in intra­molecular N—H(...)O hydrogen bonds with the phen­oxy groups and nitrate ligands. One O atom of one nitrate group is disordered over two sites of equal occupancy.

Related literature

For Schiff base ligands derived from o-vanillin and aniline and their rare earth complexes, see: Burrows & Bailar (1966 [triangle]); Li et al. (2008 [triangle]); Xian et al. (2008 [triangle]); Zhao et al. (2007 [triangle]). For their applications, see: Leadbeater & Marco (2002 [triangle]); Quici et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1332-scheme1.jpg

Experimental

Crystal data

  • [La(NO3)3(C15H15NO2)2(CH4O)]
  • M r = 839.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1332-efi1.jpg
  • a = 7.8616 (2) Å
  • b = 14.6502 (5) Å
  • c = 16.6470 (5) Å
  • α = 73.210 (2)°
  • β = 85.648 (2)°
  • γ = 79.320 (1)°
  • V = 1803.26 (9) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.26 mm−1
  • T = 296 K
  • 0.43 × 0.31 × 0.20 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.634, T max = 0.783
  • 30011 measured reflections
  • 8464 independent reflections
  • 7465 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.101
  • S = 1.08
  • 8464 reflections
  • 473 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.23 e Å−3
  • Δρmin = −0.51 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: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038109/bh2313sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810038109/bh2313Isup2.hkl

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

supplementary crystallographic information

Comment

Schiff base ligands derived from substituted o-vanillin and aniline and their rare earth metal complexes have generated considerable attention in the past decades, due to their intriguing novel structural features (Burrows & Bailar, 1966; Zhao et al., 2007; Xian et al., 2008; Li et al., 2008) and promising applications in various fields such as catalysis, optoelectronic devices, and so on (Leadbeater & Marco, 2002; Quici et al., 2004). Interested in this field, we have been engaged in a major effort directed toward the synthesis of new analogous Schiff base derived from o-vanillin and their rare metal complexes. In few previous articles, we have reported our partial research results (Zhao et al., 2007; Xian et al., 2008; Li et al., 2008). Herein, we describe a new La(III) complex.

The single-crystal structure is shown in Fig. 1, which illustrates that the La(III) ion in this complex is eleven-coordinated by six O atoms from three nitrate radical ions, four O atoms from the Schiff bases, and one O atom from methanol. The Schiff bases are coordinated to the La(III) ion in the bidentate mode, using O atoms from methoxy groups and deprotonated phenolic hydroxyl groups. The bonds between La(III) and O atoms from phenoxy groups are 2.429 (2) and 2.482 (2) Å, which are shorter than those between La(III) and O atoms of methoxy groups [2.808 (2) and 2.964 (3) Å]. The nitrate radical anions coordinate to the La(III) with O atoms with the distances ranging from 2.574 (19) to 2.741 (3) Å, which are intermediate between the La—O(phenolic) and the La—O(methoxy) bond lengths. The La—O(methanol) bong length is only slightly longer than the La—O(phenolic). In addition, the O5 atom in a nitrate anion is disordered over two sites.

The hydrogen bonds and π···π weak non-covalent interactions give stability to the crystal structure. In each HL ligand, the proton of phenolic hydroxyl group is transferred to the imine N atom, which is involved in the formation of intramolecular hydrogen bonds. There are no classic hydrogen bonds between the adjacent molecules. π···π interactions exist in the crystal between symmetry-related molecules.

Experimental

Reagents and solvents are commercially available and were not purified before use. The Schiff base ligand 2-[(4-methylphenyl)iminomethyl]-6-methoxy-phenol was synthesized by condensation of o-vanillin and p-methylaniline. The title complex was obtained by adding La(NO3)3 (1 mmol, dissolved in 20 ml methanol) to N-salicylidene-p-toluidine (2 mmol) in methanol. The mixture was stirred for 8 h at room temperature. The resulting solid was then filtered out and the reddish-brown solution was kept aside. Red crystals were obtained after several days.

Refinement

The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C)) and N—H = 0.86 Å, Uiso(H) = 1.2Ueq(N)]. H atom of the hydroxyl group in methanol, H14, was found in a difference map and refined freely.

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

[La(NO3)3(C15H15NO2)2(CH4O)]Z = 2
Mr = 839.54F(000) = 848
Triclinic, P1Dx = 1.546 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8616 (2) ÅCell parameters from 9937 reflections
b = 14.6502 (5) Åθ = 1.5–27.7°
c = 16.6470 (5) ŵ = 1.26 mm1
α = 73.210 (2)°T = 296 K
β = 85.648 (2)°Block, red
γ = 79.320 (1)°0.43 × 0.31 × 0.20 mm
V = 1803.26 (9) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer8464 independent reflections
Radiation source: fine-focus sealed tube7465 reflections with I > 2σ(I)
graphiteRint = 0.024
[var phi] and ω scansθmax = 27.7°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→10
Tmin = 0.634, Tmax = 0.783k = −19→18
30011 measured reflectionsl = −21→21

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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8812P] where P = (Fo2 + 2Fc2)/3
8464 reflections(Δ/σ)max = 0.001
473 parametersΔρmax = 1.23 e Å3
0 restraintsΔρmin = −0.51 e Å3
0 constraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
La0.50959 (2)0.172767 (11)0.194416 (10)0.04293 (7)
O10.3524 (3)0.32578 (16)0.11163 (14)0.0509 (5)
O20.4089 (4)0.20682 (18)0.01876 (17)0.0673 (7)
O30.4311 (3)0.05673 (16)0.32705 (14)0.0534 (5)
O40.2435 (3)0.23100 (17)0.30077 (18)0.0668 (7)
O50.665 (2)0.0504 (12)0.1156 (11)0.093 (5)0.50
O5'0.610 (3)0.0211 (12)0.1433 (13)0.118 (7)0.50
O60.7262 (5)−0.0014 (2)0.2482 (2)0.0983 (11)
O70.8172 (5)−0.0934 (3)0.1712 (3)0.1174 (14)
O80.8476 (4)0.1764 (3)0.17935 (19)0.0857 (9)
O90.7128 (4)0.2593 (2)0.06973 (19)0.0807 (9)
O100.9881 (4)0.2497 (3)0.0703 (2)0.0941 (11)
O110.5728 (4)0.32810 (17)0.22884 (17)0.0652 (6)
O120.6419 (4)0.19922 (19)0.32788 (15)0.0659 (6)
O130.6879 (4)0.3357 (2)0.34005 (19)0.0815 (8)
O140.2457 (4)0.1086 (3)0.1706 (2)0.0912 (11)
N10.2882 (4)0.50830 (19)0.11960 (17)0.0521 (6)
H1A0.33980.45020.14210.063*
N20.5013 (3)−0.12440 (19)0.41794 (17)0.0486 (6)
H2A0.5240−0.08010.37380.058*
N30.7281 (5)−0.0207 (2)0.1827 (3)0.0753 (9)
N40.8512 (4)0.2286 (2)0.10540 (19)0.0582 (7)
N50.6358 (4)0.2885 (2)0.29964 (18)0.0542 (6)
C10.2592 (5)0.4606 (2)−0.0041 (2)0.0548 (8)
C20.3205 (4)0.3609 (2)0.03234 (19)0.0453 (6)
C30.3459 (4)0.3002 (2)−0.0216 (2)0.0523 (7)
C40.3071 (6)0.3360 (3)−0.1045 (2)0.0694 (10)
H4A0.32380.2945−0.13860.083*
C50.2422 (7)0.4346 (3)−0.1392 (2)0.0822 (13)
H5A0.21640.4580−0.19590.099*
C60.2170 (7)0.4957 (3)−0.0904 (2)0.0775 (12)
H6A0.17200.5608−0.11330.093*
C70.2388 (5)0.5277 (2)0.0433 (2)0.0611 (9)
H7A0.18580.59070.01770.073*
C80.4344 (12)0.1407 (4)−0.0311 (5)0.162 (4)
H8C0.49550.07940.00060.194*
H8A0.50060.1657−0.08080.194*
H8B0.32400.1327−0.04650.194*
C90.2656 (4)0.5737 (2)0.1702 (2)0.0512 (7)
C100.3521 (6)0.5460 (3)0.2447 (3)0.0675 (10)
H10A0.42550.48660.26050.081*
C110.3294 (6)0.6071 (3)0.2957 (3)0.0724 (11)
H11A0.38750.58820.34600.087*
C120.2219 (5)0.6955 (3)0.2731 (3)0.0651 (9)
C130.1410 (6)0.7226 (3)0.1976 (3)0.0747 (11)
H13A0.07130.78320.18080.090*
C140.1595 (6)0.6631 (3)0.1459 (3)0.0683 (10)
H14A0.10180.68260.09540.082*
C150.1923 (7)0.7602 (4)0.3311 (4)0.0954 (16)
H15A0.11480.81870.30550.143*
H15B0.30080.77580.34090.143*
H15C0.14270.72720.38340.143*
C160.3056 (4)−0.0007 (2)0.4620 (2)0.0464 (7)
C170.3251 (4)0.0727 (2)0.3862 (2)0.0463 (6)
C180.2207 (4)0.1652 (2)0.3780 (2)0.0535 (7)
C190.1127 (5)0.1833 (3)0.4407 (3)0.0617 (9)
H19A0.04620.24440.43380.074*
C200.0999 (5)0.1110 (3)0.5159 (3)0.0654 (10)
H20A0.02660.12490.55890.078*
C210.1928 (5)0.0211 (3)0.5269 (2)0.0574 (8)
H21A0.1826−0.02640.57710.069*
C220.3935 (4)−0.0961 (2)0.4727 (2)0.0495 (7)
H22A0.3732−0.14220.52250.059*
C230.1142 (7)0.3155 (3)0.2773 (4)0.108 (2)
H23A0.03860.31970.32470.162*
H23B0.04830.31200.23240.162*
H23C0.16870.37180.25910.162*
C240.5857 (4)−0.2201 (2)0.4228 (2)0.0514 (7)
C250.6855 (6)−0.2367 (3)0.3564 (3)0.0787 (12)
H25A0.6994−0.18530.30960.094*
C260.7662 (6)−0.3292 (3)0.3578 (3)0.0841 (13)
H26A0.8345−0.33870.31180.101*
C270.7489 (6)−0.4063 (3)0.4239 (3)0.0730 (11)
C280.6463 (9)−0.3883 (3)0.4903 (3)0.1021 (18)
H28A0.6307−0.44000.53650.122*
C290.5661 (8)−0.2968 (3)0.4906 (3)0.0885 (15)
H29A0.4988−0.28710.53680.106*
C300.8370 (9)−0.5076 (4)0.4238 (4)0.109 (2)
H30A0.8078−0.55300.47500.163*
H30B0.9602−0.51030.41950.163*
H30C0.7988−0.52340.37690.163*
C310.1924 (9)0.0164 (4)0.2049 (5)0.137 (3)
H31A0.08370.01740.18180.205*
H31B0.17980.00300.26480.205*
H31C0.2781−0.03300.19120.205*
H140.166 (8)0.151 (4)0.140 (4)0.107 (18)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
La0.04001 (10)0.03162 (10)0.05135 (11)−0.00059 (6)−0.00069 (7)−0.00613 (7)
O10.0568 (13)0.0394 (11)0.0507 (12)0.0028 (9)−0.0089 (10)−0.0083 (9)
O20.0818 (18)0.0450 (13)0.0776 (17)0.0009 (12)−0.0210 (14)−0.0238 (12)
O30.0528 (12)0.0415 (11)0.0574 (13)−0.0024 (9)0.0127 (10)−0.0076 (10)
O40.0578 (14)0.0412 (12)0.0850 (17)0.0052 (10)0.0178 (13)−0.0056 (12)
O50.110 (12)0.067 (7)0.104 (8)0.032 (6)−0.050 (7)−0.043 (6)
O5'0.101 (11)0.094 (12)0.174 (18)0.049 (8)−0.058 (10)−0.087 (12)
O60.119 (3)0.071 (2)0.086 (2)0.0160 (19)0.017 (2)−0.0171 (17)
O70.124 (3)0.079 (2)0.137 (3)0.052 (2)−0.015 (3)−0.052 (2)
O80.0601 (16)0.105 (2)0.0719 (18)−0.0099 (16)−0.0042 (14)0.0051 (17)
O90.0552 (16)0.095 (2)0.0764 (18)−0.0136 (15)−0.0031 (13)0.0012 (16)
O100.0467 (14)0.114 (3)0.093 (2)−0.0199 (16)0.0056 (14)0.0177 (19)
O110.0798 (17)0.0453 (13)0.0675 (15)−0.0025 (12)−0.0209 (13)−0.0115 (11)
O120.0837 (18)0.0540 (15)0.0525 (13)−0.0075 (13)−0.0064 (12)−0.0044 (11)
O130.083 (2)0.096 (2)0.0820 (19)−0.0218 (17)−0.0105 (15)−0.0456 (17)
O140.0644 (18)0.075 (2)0.118 (3)−0.0223 (16)−0.0334 (18)0.0124 (19)
N10.0589 (16)0.0360 (13)0.0546 (15)0.0036 (11)0.0003 (12)−0.0096 (11)
N20.0531 (15)0.0417 (14)0.0496 (14)−0.0111 (11)−0.0007 (11)−0.0091 (11)
N30.067 (2)0.0517 (18)0.103 (3)0.0121 (16)−0.003 (2)−0.0288 (19)
N40.0460 (15)0.0540 (17)0.0614 (17)−0.0079 (12)−0.0002 (13)0.0039 (13)
N50.0507 (15)0.0585 (17)0.0544 (15)−0.0073 (13)0.0012 (12)−0.0192 (13)
C10.065 (2)0.0433 (17)0.0476 (16)−0.0017 (15)0.0010 (15)−0.0053 (13)
C20.0413 (15)0.0434 (16)0.0487 (16)−0.0046 (12)−0.0021 (12)−0.0103 (13)
C30.0495 (17)0.0488 (18)0.0593 (18)−0.0070 (14)−0.0040 (14)−0.0166 (15)
C40.084 (3)0.069 (3)0.060 (2)−0.011 (2)−0.0033 (19)−0.0273 (19)
C50.121 (4)0.071 (3)0.0464 (19)−0.008 (3)−0.010 (2)−0.0080 (18)
C60.114 (4)0.051 (2)0.055 (2)0.000 (2)−0.009 (2)−0.0021 (17)
C70.079 (2)0.0389 (17)0.0545 (19)0.0021 (16)0.0017 (17)−0.0045 (14)
C80.268 (10)0.070 (3)0.159 (6)0.047 (5)−0.110 (7)−0.072 (4)
C90.0521 (17)0.0398 (16)0.0586 (18)−0.0004 (13)0.0020 (14)−0.0145 (14)
C100.080 (3)0.0431 (18)0.073 (2)0.0112 (17)−0.016 (2)−0.0168 (17)
C110.086 (3)0.057 (2)0.075 (2)0.002 (2)−0.020 (2)−0.0235 (19)
C120.061 (2)0.054 (2)0.086 (3)−0.0032 (17)−0.0025 (19)−0.0319 (19)
C130.078 (3)0.051 (2)0.091 (3)0.0182 (19)−0.013 (2)−0.029 (2)
C140.075 (2)0.051 (2)0.071 (2)0.0181 (18)−0.0130 (19)−0.0204 (17)
C150.103 (4)0.078 (3)0.121 (4)0.002 (3)−0.016 (3)−0.060 (3)
C160.0428 (15)0.0488 (17)0.0517 (16)−0.0143 (13)−0.0006 (12)−0.0164 (13)
C170.0391 (14)0.0462 (16)0.0559 (17)−0.0101 (12)0.0028 (12)−0.0170 (14)
C180.0452 (16)0.0453 (17)0.069 (2)−0.0086 (13)0.0073 (14)−0.0165 (15)
C190.0544 (19)0.056 (2)0.079 (2)−0.0056 (16)0.0100 (17)−0.0302 (18)
C200.059 (2)0.081 (3)0.067 (2)−0.0169 (19)0.0161 (17)−0.040 (2)
C210.059 (2)0.068 (2)0.0501 (17)−0.0175 (17)0.0057 (15)−0.0211 (16)
C220.0530 (17)0.0502 (18)0.0459 (15)−0.0155 (14)−0.0042 (13)−0.0098 (13)
C230.085 (3)0.068 (3)0.124 (4)0.026 (2)0.030 (3)0.013 (3)
C240.0543 (18)0.0441 (17)0.0582 (18)−0.0107 (14)−0.0079 (14)−0.0149 (14)
C250.091 (3)0.050 (2)0.088 (3)−0.011 (2)0.025 (2)−0.016 (2)
C260.087 (3)0.065 (3)0.104 (3)−0.010 (2)0.022 (3)−0.037 (3)
C270.080 (3)0.048 (2)0.096 (3)−0.0049 (19)−0.019 (2)−0.026 (2)
C280.160 (6)0.052 (2)0.082 (3)−0.003 (3)−0.004 (3)−0.009 (2)
C290.136 (4)0.053 (2)0.061 (2)0.000 (2)0.014 (3)−0.0070 (19)
C300.128 (5)0.064 (3)0.145 (5)0.008 (3)−0.027 (4)−0.054 (3)
C310.117 (5)0.084 (4)0.205 (8)−0.049 (4)−0.060 (5)0.001 (4)

Geometric parameters (Å, °)

La—O12.429 (2)C8—H8A0.9600
La—O32.482 (2)C8—H8B0.9600
La—O142.532 (3)C9—C101.378 (5)
La—O5'2.574 (19)C9—C141.384 (5)
La—O52.59 (2)C10—C111.383 (5)
La—O112.640 (2)C10—H10A0.9300
La—O82.659 (3)C11—C121.376 (5)
La—O122.677 (3)C11—H11A0.9300
La—O92.682 (3)C12—C131.372 (6)
La—O62.741 (3)C12—C151.515 (5)
La—O42.808 (2)C13—C141.374 (5)
La—O22.964 (3)C13—H13A0.9300
O1—C21.296 (4)C14—H14A0.9300
O2—C31.355 (4)C15—H15A0.9600
O2—C81.426 (5)C15—H15B0.9600
O3—C171.287 (4)C15—H15C0.9600
O4—C181.388 (4)C16—C221.406 (5)
O4—C231.426 (5)C16—C211.416 (5)
O5—N31.342 (18)C16—C171.422 (5)
O5'—N31.15 (2)C17—C181.423 (4)
O6—N31.201 (5)C18—C191.351 (5)
O7—N31.218 (4)C19—C201.397 (6)
O8—N41.249 (4)C19—H19A0.9300
O9—N41.225 (4)C20—C211.350 (6)
O10—N41.232 (4)C20—H20A0.9300
O11—N51.248 (4)C21—H21A0.9300
O12—N51.248 (4)C22—H22A0.9300
O13—N51.230 (4)C23—H23A0.9600
O14—C311.434 (6)C23—H23B0.9600
O14—H140.87 (6)C23—H23C0.9600
N1—C71.293 (4)C24—C251.361 (5)
N1—C91.428 (4)C24—C291.366 (5)
N1—H1A0.8600C25—C261.380 (6)
N2—C221.301 (4)C25—H25A0.9300
N2—C241.417 (4)C26—C271.350 (7)
N2—H2A0.8600C26—H26A0.9300
C1—C71.408 (5)C27—C281.375 (7)
C1—C21.416 (4)C27—C301.518 (6)
C1—C61.421 (5)C28—C291.373 (6)
C2—C31.416 (4)C28—H28A0.9300
C3—C41.364 (5)C29—H29A0.9300
C4—C51.403 (6)C30—H30A0.9600
C4—H4A0.9300C30—H30B0.9600
C5—C61.354 (6)C30—H30C0.9600
C5—H5A0.9300C31—H31A0.9600
C6—H6A0.9300C31—H31B0.9600
C7—H7A0.9300C31—H31C0.9600
C8—H8C0.9600
O1—La—O3131.51 (8)O1—C2—C3120.9 (3)
O1—La—O1483.19 (10)O1—C2—C1121.9 (3)
O3—La—O1471.17 (10)C3—C2—C1117.2 (3)
O1—La—O5'125.4 (5)O2—C3—C4126.2 (3)
O3—La—O5'84.7 (4)O2—C3—C2112.6 (3)
O14—La—O5'71.2 (4)C4—C3—C2121.2 (3)
O1—La—O5117.8 (4)C3—C4—C5120.8 (4)
O3—La—O599.1 (3)C3—C4—H4A119.6
O14—La—O582.3 (4)C5—C4—H4A119.6
O5'—La—O515.8 (6)C6—C5—C4120.2 (4)
O1—La—O1164.68 (8)C6—C5—H5A119.9
O3—La—O11108.70 (8)C4—C5—H5A119.9
O14—La—O11136.91 (11)C5—C6—C1120.1 (4)
O5'—La—O11151.1 (4)C5—C6—H6A119.9
O5—La—O11137.2 (4)C1—C6—H6A119.9
O1—La—O8109.57 (9)N1—C7—C1125.0 (3)
O3—La—O8112.38 (8)N1—C7—H7A117.5
O14—La—O8151.69 (14)C1—C7—H7A117.5
O5'—La—O881.0 (4)O2—C8—H8C109.5
O5—La—O869.4 (4)O2—C8—H8A109.5
O11—La—O870.22 (10)H8C—C8—H8A109.5
O1—La—O12109.48 (8)O2—C8—H8B109.5
O3—La—O1268.27 (8)H8C—C8—H8B109.5
O14—La—O12134.66 (11)H8A—C8—H8B109.5
O5'—La—O12123.0 (5)C10—C9—C14120.1 (3)
O5—La—O12123.1 (4)C10—C9—N1118.6 (3)
O11—La—O1247.22 (8)C14—C9—N1121.4 (3)
O8—La—O1266.28 (10)C9—C10—C11119.7 (3)
O1—La—O969.51 (9)C9—C10—H10A120.2
O3—La—O9158.15 (9)C11—C10—H10A120.2
O14—La—O9123.52 (11)C12—C11—C10121.0 (4)
O5'—La—O985.6 (4)C12—C11—H11A119.5
O5—La—O969.8 (3)C10—C11—H11A119.5
O11—La—O972.62 (10)C13—C12—C11118.3 (3)
O8—La—O946.59 (9)C13—C12—C15121.2 (4)
O12—La—O9101.36 (9)C11—C12—C15120.5 (4)
O1—La—O6165.10 (9)C12—C13—C14122.1 (3)
O3—La—O661.97 (9)C12—C13—H13A118.9
O14—La—O697.88 (12)C14—C13—H13A118.9
O5'—La—O642.8 (5)C13—C14—C9118.9 (4)
O5—La—O648.1 (4)C13—C14—H14A120.6
O11—La—O6120.64 (11)C9—C14—H14A120.6
O8—La—O663.33 (12)C12—C15—H15A109.5
O12—La—O680.39 (10)C12—C15—H15B109.5
O9—La—O698.05 (11)H15A—C15—H15B109.5
O1—La—O474.24 (7)C12—C15—H15C109.5
O3—La—O459.36 (7)H15A—C15—H15C109.5
O14—La—O473.01 (12)H15B—C15—H15C109.5
O5'—La—O4135.7 (4)C22—C16—C21119.2 (3)
O5—La—O4151.3 (4)C22—C16—C17120.8 (3)
O11—La—O471.17 (9)C21—C16—C17120.0 (3)
O8—La—O4134.08 (10)O3—C17—C16121.9 (3)
O12—La—O469.48 (9)O3—C17—C18121.1 (3)
O9—La—O4136.83 (9)C16—C17—C18117.1 (3)
O6—La—O4120.37 (9)C19—C18—O4125.7 (3)
O1—La—O256.74 (7)C19—C18—C17121.4 (3)
O3—La—O2131.40 (8)O4—C18—C17113.0 (3)
O14—La—O262.19 (10)C18—C19—C20120.6 (3)
O5'—La—O268.6 (5)C18—C19—H19A119.7
O5—La—O263.1 (4)C20—C19—H19A119.7
O11—La—O2114.18 (7)C21—C20—C19120.9 (3)
O8—La—O2102.91 (9)C21—C20—H20A119.6
O12—La—O2160.04 (8)C19—C20—H20A119.6
O9—La—O261.45 (9)C20—C21—C16120.1 (3)
O6—La—O2110.58 (9)C20—C21—H21A120.0
O4—La—O2115.03 (8)C16—C21—H21A120.0
C2—O1—La133.08 (19)N2—C22—C16124.7 (3)
C3—O2—C8115.9 (4)N2—C22—H22A117.7
C3—O2—La114.91 (19)C16—C22—H22A117.7
C8—O2—La128.8 (3)O4—C23—H23A109.5
C17—O3—La128.9 (2)O4—C23—H23B109.5
C18—O4—C23117.0 (3)H23A—C23—H23B109.5
C18—O4—La117.00 (18)O4—C23—H23C109.5
C23—O4—La125.3 (3)H23A—C23—H23C109.5
N3—O5—La97.9 (10)H23B—C23—H23C109.5
N3—O5'—La105.2 (13)C25—C24—C29118.7 (4)
N3—O6—La94.6 (2)C25—C24—N2118.8 (3)
N4—O8—La98.3 (2)C29—C24—N2122.5 (3)
N4—O9—La97.8 (2)C24—C25—C26120.6 (4)
N5—O11—La98.73 (19)C24—C25—H25A119.7
N5—O12—La96.91 (18)C26—C25—H25A119.7
C31—O14—La131.9 (3)C27—C26—C25121.9 (4)
C31—O14—H14112 (4)C27—C26—H26A119.0
La—O14—H14116 (4)C25—C26—H26A119.0
C7—N1—C9126.5 (3)C26—C27—C28116.8 (4)
C7—N1—H1A116.7C26—C27—C30121.1 (5)
C9—N1—H1A116.7C28—C27—C30122.1 (5)
C22—N2—C24127.3 (3)C29—C28—C27122.4 (5)
C22—N2—H2A116.4C29—C28—H28A118.8
C24—N2—H2A116.4C27—C28—H28A118.8
O5'—N3—O6112.0 (11)C24—C29—C28119.7 (4)
O5'—N3—O7123.3 (11)C24—C29—H29A120.2
O6—N3—O7122.0 (4)C28—C29—H29A120.2
O5'—N3—O532.1 (13)C27—C30—H30A109.5
O6—N3—O5117.7 (9)C27—C30—H30B109.5
O7—N3—O5118.3 (9)H30A—C30—H30B109.5
O9—N4—O10121.4 (3)C27—C30—H30C109.5
O9—N4—O8117.3 (3)H30A—C30—H30C109.5
O10—N4—O8121.3 (3)H30B—C30—H30C109.5
O13—N5—O11121.3 (3)O14—C31—H31A109.5
O13—N5—O12121.6 (3)O14—C31—H31B109.5
O11—N5—O12117.1 (3)H31A—C31—H31B109.5
C7—C1—C2121.5 (3)O14—C31—H31C109.5
C7—C1—C6118.1 (3)H31A—C31—H31C109.5
C2—C1—C6120.4 (3)H31B—C31—H31C109.5
O3—La—O1—C2−131.3 (3)O1—La—O11—N5161.2 (2)
O14—La—O1—C2−74.0 (3)O3—La—O11—N533.3 (2)
O5'—La—O1—C2−12.8 (6)O14—La—O11—N5115.4 (2)
O5—La—O1—C23.6 (5)O5'—La—O11—N5−80.9 (10)
O11—La—O1—C2135.5 (3)O5—La—O11—N5−94.4 (6)
O8—La—O1—C280.0 (3)O8—La—O11—N5−74.5 (2)
O12—La—O1—C2150.9 (3)O12—La—O11—N51.05 (18)
O9—La—O1—C255.7 (3)O9—La—O11—N5−123.8 (2)
O6—La—O1—C221.1 (5)O6—La—O11—N5−34.6 (2)
O4—La—O1—C2−148.2 (3)O4—La—O11—N580.1 (2)
O2—La—O1—C2−12.9 (3)O2—La—O11—N5−170.17 (19)
O1—La—O2—C39.7 (2)O1—La—O12—N5−20.1 (2)
O3—La—O2—C3128.2 (2)O3—La—O12—N5−148.1 (2)
O14—La—O2—C3110.3 (3)O14—La—O12—N5−120.0 (2)
O5'—La—O2—C3−170.3 (5)O5'—La—O12—N5144.1 (5)
O5—La—O2—C3−154.0 (5)O5—La—O12—N5125.2 (4)
O11—La—O2—C3−21.6 (3)O11—La—O12—N5−1.04 (18)
O8—La—O2—C3−95.5 (2)O8—La—O12—N583.4 (2)
O12—La—O2—C3−40.7 (4)O9—La—O12—N552.0 (2)
O9—La—O2—C3−73.5 (2)O6—La—O12—N5148.4 (2)
O6—La—O2—C3−161.5 (2)O4—La—O12—N5−84.0 (2)
O4—La—O2—C358.0 (3)O2—La—O12—N523.0 (4)
O1—La—O2—C8−177.5 (6)O1—La—O14—C31−171.4 (6)
O3—La—O2—C8−58.9 (6)O3—La—O14—C31−33.1 (6)
O14—La—O2—C8−76.8 (6)O5'—La—O14—C3157.6 (8)
O5'—La—O2—C82.6 (7)O5—La—O14—C3169.3 (7)
O5—La—O2—C818.9 (7)O11—La—O14—C31−130.7 (6)
O11—La—O2—C8151.3 (6)O8—La—O14—C3169.3 (7)
O8—La—O2—C877.4 (6)O12—La—O14—C31−60.6 (7)
O12—La—O2—C8132.1 (6)O9—La—O14—C31128.8 (6)
O9—La—O2—C899.4 (6)O6—La—O14—C3123.6 (6)
O6—La—O2—C811.3 (6)O4—La—O14—C31−95.8 (6)
O4—La—O2—C8−129.2 (6)O2—La—O14—C31132.8 (6)
O1—La—O3—C17−25.9 (3)La—O5'—N3—O624.1 (11)
O14—La—O3—C17−87.9 (3)La—O5'—N3—O7−174.5 (4)
O5'—La—O3—C17−159.9 (5)La—O5'—N3—O5−83 (3)
O5—La—O3—C17−166.5 (5)La—O6—N3—O5'−21.8 (10)
O11—La—O3—C1746.5 (3)La—O6—N3—O7176.6 (4)
O8—La—O3—C17122.2 (3)La—O6—N3—O513.1 (9)
O12—La—O3—C1771.4 (3)La—O5—N3—O5'74 (3)
O9—La—O3—C17136.3 (3)La—O5—N3—O6−13.9 (10)
O6—La—O3—C17161.9 (3)La—O5—N3—O7−178.0 (4)
O4—La—O3—C17−6.9 (2)La—O9—N4—O10179.3 (3)
O2—La—O3—C17−104.6 (3)La—O9—N4—O8−1.8 (4)
O1—La—O4—C18172.4 (3)La—O8—N4—O91.9 (4)
O3—La—O4—C187.0 (2)La—O8—N4—O10−179.3 (3)
O14—La—O4—C1884.9 (2)La—O11—N5—O13178.8 (3)
O5'—La—O4—C1847.5 (7)La—O11—N5—O12−1.8 (3)
O5—La—O4—C1852.8 (9)La—O12—N5—O13−178.9 (3)
O11—La—O4—C18−119.5 (2)La—O12—N5—O111.8 (3)
O8—La—O4—C18−85.4 (3)La—O1—C2—C314.8 (4)
O12—La—O4—C18−69.2 (2)La—O1—C2—C1−165.3 (2)
O9—La—O4—C18−153.9 (2)C7—C1—C2—O13.6 (5)
O6—La—O4—C18−4.4 (3)C6—C1—C2—O1−176.7 (4)
O2—La—O4—C18131.9 (2)C7—C1—C2—C3−176.5 (3)
O1—La—O4—C232.6 (4)C6—C1—C2—C33.2 (5)
O3—La—O4—C23−162.7 (4)C8—O2—C3—C4−0.7 (7)
O14—La—O4—C23−84.9 (4)La—O2—C3—C4173.1 (3)
O5'—La—O4—C23−122.3 (8)C8—O2—C3—C2178.7 (5)
O5—La—O4—C23−117.0 (9)La—O2—C3—C2−7.5 (4)
O11—La—O4—C2370.7 (4)O1—C2—C3—O2−1.7 (4)
O8—La—O4—C23104.8 (4)C1—C2—C3—O2178.4 (3)
O12—La—O4—C23121.0 (4)O1—C2—C3—C4177.8 (3)
O9—La—O4—C2336.3 (4)C1—C2—C3—C4−2.2 (5)
O6—La—O4—C23−174.2 (4)O2—C3—C4—C5180.0 (4)
O2—La—O4—C23−37.9 (4)C2—C3—C4—C50.6 (6)
O1—La—O5—N3−178.7 (6)C3—C4—C5—C6−0.1 (8)
O3—La—O5—N3−31.2 (9)C4—C5—C6—C11.2 (8)
O14—La—O5—N3−100.7 (8)C7—C1—C6—C5176.9 (5)
O5'—La—O5—N3−56 (3)C2—C1—C6—C5−2.8 (7)
O11—La—O5—N399.4 (8)C9—N1—C7—C1−178.2 (4)
O8—La—O5—N379.4 (8)C2—C1—C7—N17.1 (6)
O12—La—O5—N338.7 (10)C6—C1—C7—N1−172.6 (4)
O9—La—O5—N3129.3 (9)C7—N1—C9—C10−168.9 (4)
O6—La—O5—N37.2 (5)C7—N1—C9—C1411.1 (6)
O4—La—O5—N3−69.8 (13)C14—C9—C10—C111.5 (6)
O2—La—O5—N3−163.3 (10)N1—C9—C10—C11−178.6 (4)
O1—La—O5'—N3153.7 (9)C9—C10—C11—C12−0.3 (7)
O3—La—O5'—N3−67.7 (11)C10—C11—C12—C13−1.5 (7)
O14—La—O5'—N3−139.6 (12)C10—C11—C12—C15177.6 (5)
O5—La—O5'—N388 (3)C11—C12—C13—C142.2 (7)
O11—La—O5'—N352.1 (17)C15—C12—C13—C14−176.9 (5)
O8—La—O5'—N346.0 (10)C12—C13—C14—C9−1.1 (7)
O12—La—O5'—N3−7.9 (13)C10—C9—C14—C13−0.8 (6)
O9—La—O5'—N392.7 (11)N1—C9—C14—C13179.2 (4)
O6—La—O5'—N3−14.2 (7)La—O3—C17—C16−174.5 (2)
O4—La—O5'—N3−101.8 (11)La—O3—C17—C186.2 (4)
O2—La—O5'—N3153.8 (12)C22—C16—C17—O3−4.4 (5)
O1—La—O6—N3−28.9 (6)C21—C16—C17—O3177.4 (3)
O3—La—O6—N3127.9 (3)C22—C16—C17—C18175.0 (3)
O14—La—O6—N364.2 (3)C21—C16—C17—C18−3.2 (4)
O5'—La—O6—N313.1 (6)C23—O4—C18—C19−16.6 (6)
O5—La—O6—N3−8.0 (5)La—O4—C18—C19172.7 (3)
O11—La—O6—N3−135.9 (3)C23—O4—C18—C17163.4 (4)
O8—La—O6—N3−93.5 (3)La—O4—C18—C17−7.2 (4)
O12—La—O6—N3−161.7 (3)O3—C17—C18—C19−178.1 (3)
O9—La—O6—N3−61.4 (3)C16—C17—C18—C192.5 (5)
O4—La—O6—N3139.1 (3)O3—C17—C18—O41.8 (4)
O2—La—O6—N31.0 (3)C16—C17—C18—O4−177.6 (3)
O1—La—O8—N4−33.1 (3)O4—C18—C19—C20179.8 (3)
O3—La—O8—N4171.8 (2)C17—C18—C19—C20−0.3 (6)
O14—La—O8—N480.2 (3)C18—C19—C20—C21−1.2 (6)
O5'—La—O8—N491.4 (5)C19—C20—C21—C160.4 (6)
O5—La—O8—N480.2 (5)C22—C16—C21—C20−176.3 (3)
O11—La—O8—N4−85.5 (3)C17—C16—C21—C201.9 (5)
O12—La—O8—N4−136.4 (3)C24—N2—C22—C16−175.9 (3)
O9—La—O8—N4−1.0 (2)C21—C16—C22—N2−179.3 (3)
O6—La—O8—N4132.6 (3)C17—C16—C22—N22.5 (5)
O4—La—O8—N4−119.8 (2)C22—N2—C24—C25175.6 (4)
O2—La—O8—N425.9 (3)C22—N2—C24—C29−2.3 (6)
O1—La—O9—N4148.8 (3)C29—C24—C25—C26−0.4 (7)
O3—La—O9—N4−17.0 (4)N2—C24—C25—C26−178.4 (4)
O14—La—O9—N4−144.7 (2)C24—C25—C26—C270.5 (8)
O5'—La—O9—N4−80.7 (5)C25—C26—C27—C280.1 (8)
O5—La—O9—N4−79.2 (5)C25—C26—C27—C30179.3 (5)
O11—La—O9—N480.0 (2)C26—C27—C28—C29−0.7 (9)
O8—La—O9—N41.1 (2)C30—C27—C28—C29−179.9 (6)
O12—La—O9—N442.1 (3)C25—C24—C29—C28−0.2 (8)
O6—La—O9—N4−39.7 (3)N2—C24—C29—C28177.6 (5)
O4—La—O9—N4114.1 (2)C27—C28—C29—C240.8 (9)
O2—La—O9—N4−148.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.012.668 (3)132
N1—H1A···O110.862.523.307 (4)153
N2—H2A···O30.861.952.627 (3)135
N2—H2A···O60.862.653.440 (5)154

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2313).

References

  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Burrows, R. C. & Bailar, J. C. (1966). J. Am. Chem. Soc.88, 4150–4156.
  • Leadbeater, N. E. & Marco, M. (2002). Chem. Rev.102, 3217–3273. [PubMed]
  • Li, H.-Q., Xian, H.-D., Liu, J.-F. & Zhao, G.-L. (2008). Acta Cryst. E64, m1593–m1594. [PMC free article] [PubMed]
  • Quici, S., Marzanni, G., Forni, A., Accorsi, G. & Barigelletti, F. (2004). Inorg. Chem.43, 1294–1301. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xian, H.-D., Liu, J.-F., Li, H.-Q. & Zhao, G.-L. (2008). Acta Cryst. E64, m1422. [PMC free article] [PubMed]
  • Zhao, G.-L., Shi, X. & Ng, S. W. (2007). Acta Cryst. E63, m267–m268.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography