Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810038109/bh2313sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810038109/bh2313Isup2.hkl
Contains datablock I

CCDC reference: 797685

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.034
  • wR factor = 0.101
  • Data-to-parameter ratio = 17.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O6 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O8 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for La PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.58 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O8 -- N4 .. 5.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O11 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O12 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C24 -C29 1.37 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H19A .. H23A .. 1.83 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 66.00 A   3 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 10 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. O6 .. 2.65 Ang. PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 103
Alert level G PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O6 .. 14.47 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O8 .. 10.97 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O9 .. 9.48 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O11 .. 6.17 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O12 .. 6.47 su PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 2.00 Perc. PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 32.10 Deg. O5' -N3 -O5 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 25 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
(Methanol-κO)bis{2-methoxy-6-[(4-methylphenyl)iminiomethyl]phenolato- κ2O,O'}tris(nitrato-κ2O,O')lanthanum(III) top
Crystal data top
[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 top
Bruker APEXII CCD area-detector
diffractometer
8464 independent reflections
Radiation source: fine-focus sealed tube7465 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ϕ and ω scansθmax = 27.7°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 910
Tmin = 0.634, Tmax = 0.783k = 1918
30011 measured reflectionsl = 2121
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 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
Crystal data top
[La(NO3)3(C15H15NO2)2(CH4O)]γ = 79.320 (1)°
Mr = 839.54V = 1803.26 (9) Å3
Triclinic, P1Z = 2
a = 7.8616 (2) ÅMo Kα radiation
b = 14.6502 (5) ŵ = 1.26 mm1
c = 16.6470 (5) ÅT = 296 K
α = 73.210 (2)°0.43 × 0.31 × 0.20 mm
β = 85.648 (2)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
8464 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
7465 reflections with I > 2σ(I)
Tmin = 0.634, Tmax = 0.783Rint = 0.024
30011 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.101H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 1.23 e Å3
8464 reflectionsΔρmin = 0.51 e Å3
473 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H2A0.52400.08010.37380.058*
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)
H4A0.32380.29450.13860.083*
C50.2422 (7)0.4346 (3)0.1392 (2)0.0822 (13)
H5A0.21640.45800.19590.099*
C60.2170 (7)0.4957 (3)0.0904 (2)0.0775 (12)
H6A0.17200.56080.11330.093*
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*
H8A0.50060.16570.08080.194*
H8B0.32400.13270.04650.194*
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)
H21A0.18260.02640.57710.069*
C220.3935 (4)0.0961 (2)0.4727 (2)0.0495 (7)
H22A0.37320.14220.52250.059*
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)
H25A0.69940.18530.30960.094*
C260.7662 (6)0.3292 (3)0.3578 (3)0.0841 (13)
H26A0.83450.33870.31180.101*
C270.7489 (6)0.4063 (3)0.4239 (3)0.0730 (11)
C280.6463 (9)0.3883 (3)0.4903 (3)0.1021 (18)
H28A0.63070.44000.53650.122*
C290.5661 (8)0.2968 (3)0.4906 (3)0.0885 (15)
H29A0.49880.28710.53680.106*
C300.8370 (9)0.5076 (4)0.4238 (4)0.109 (2)
H30A0.80780.55300.47500.163*
H30B0.96020.51030.41950.163*
H30C0.79880.52340.37690.163*
C310.1924 (9)0.0164 (4)0.2049 (5)0.137 (3)
H31A0.08370.01740.18180.205*
H31B0.17980.00300.26480.205*
H31C0.27810.03300.19120.205*
H140.166 (8)0.151 (4)0.140 (4)0.107 (18)*
Atomic displacement parameters (Å2) top
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, º) top
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—C2131.3 (3)O1—La—O11—N5161.2 (2)
O14—La—O1—C274.0 (3)O3—La—O11—N533.3 (2)
O5'—La—O1—C212.8 (6)O14—La—O11—N5115.4 (2)
O5—La—O1—C23.6 (5)O5'—La—O11—N580.9 (10)
O11—La—O1—C2135.5 (3)O5—La—O11—N594.4 (6)
O8—La—O1—C280.0 (3)O8—La—O11—N574.5 (2)
O12—La—O1—C2150.9 (3)O12—La—O11—N51.05 (18)
O9—La—O1—C255.7 (3)O9—La—O11—N5123.8 (2)
O6—La—O1—C221.1 (5)O6—La—O11—N534.6 (2)
O4—La—O1—C2148.2 (3)O4—La—O11—N580.1 (2)
O2—La—O1—C212.9 (3)O2—La—O11—N5170.17 (19)
O1—La—O2—C39.7 (2)O1—La—O12—N520.1 (2)
O3—La—O2—C3128.2 (2)O3—La—O12—N5148.1 (2)
O14—La—O2—C3110.3 (3)O14—La—O12—N5120.0 (2)
O5'—La—O2—C3170.3 (5)O5'—La—O12—N5144.1 (5)
O5—La—O2—C3154.0 (5)O5—La—O12—N5125.2 (4)
O11—La—O2—C321.6 (3)O11—La—O12—N51.04 (18)
O8—La—O2—C395.5 (2)O8—La—O12—N583.4 (2)
O12—La—O2—C340.7 (4)O9—La—O12—N552.0 (2)
O9—La—O2—C373.5 (2)O6—La—O12—N5148.4 (2)
O6—La—O2—C3161.5 (2)O4—La—O12—N584.0 (2)
O4—La—O2—C358.0 (3)O2—La—O12—N523.0 (4)
O1—La—O2—C8177.5 (6)O1—La—O14—C31171.4 (6)
O3—La—O2—C858.9 (6)O3—La—O14—C3133.1 (6)
O14—La—O2—C876.8 (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—C31130.7 (6)
O11—La—O2—C8151.3 (6)O8—La—O14—C3169.3 (7)
O8—La—O2—C877.4 (6)O12—La—O14—C3160.6 (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—C3195.8 (6)
O4—La—O2—C8129.2 (6)O2—La—O14—C31132.8 (6)
O1—La—O3—C1725.9 (3)La—O5'—N3—O624.1 (11)
O14—La—O3—C1787.9 (3)La—O5'—N3—O7174.5 (4)
O5'—La—O3—C17159.9 (5)La—O5'—N3—O583 (3)
O5—La—O3—C17166.5 (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—O613.9 (10)
O6—La—O3—C17161.9 (3)La—O5—N3—O7178.0 (4)
O4—La—O3—C176.9 (2)La—O9—N4—O10179.3 (3)
O2—La—O3—C17104.6 (3)La—O9—N4—O81.8 (4)
O1—La—O4—C18172.4 (3)La—O8—N4—O91.9 (4)
O3—La—O4—C187.0 (2)La—O8—N4—O10179.3 (3)
O14—La—O4—C1884.9 (2)La—O11—N5—O13178.8 (3)
O5'—La—O4—C1847.5 (7)La—O11—N5—O121.8 (3)
O5—La—O4—C1852.8 (9)La—O12—N5—O13178.9 (3)
O11—La—O4—C18119.5 (2)La—O12—N5—O111.8 (3)
O8—La—O4—C1885.4 (3)La—O1—C2—C314.8 (4)
O12—La—O4—C1869.2 (2)La—O1—C2—C1165.3 (2)
O9—La—O4—C18153.9 (2)C7—C1—C2—O13.6 (5)
O6—La—O4—C184.4 (3)C6—C1—C2—O1176.7 (4)
O2—La—O4—C18131.9 (2)C7—C1—C2—C3176.5 (3)
O1—La—O4—C232.6 (4)C6—C1—C2—C33.2 (5)
O3—La—O4—C23162.7 (4)C8—O2—C3—C40.7 (7)
O14—La—O4—C2384.9 (4)La—O2—C3—C4173.1 (3)
O5'—La—O4—C23122.3 (8)C8—O2—C3—C2178.7 (5)
O5—La—O4—C23117.0 (9)La—O2—C3—C27.5 (4)
O11—La—O4—C2370.7 (4)O1—C2—C3—O21.7 (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—C42.2 (5)
O6—La—O4—C23174.2 (4)O2—C3—C4—C5180.0 (4)
O2—La—O4—C2337.9 (4)C2—C3—C4—C50.6 (6)
O1—La—O5—N3178.7 (6)C3—C4—C5—C60.1 (8)
O3—La—O5—N331.2 (9)C4—C5—C6—C11.2 (8)
O14—La—O5—N3100.7 (8)C7—C1—C6—C5176.9 (5)
O5'—La—O5—N356 (3)C2—C1—C6—C52.8 (7)
O11—La—O5—N399.4 (8)C9—N1—C7—C1178.2 (4)
O8—La—O5—N379.4 (8)C2—C1—C7—N17.1 (6)
O12—La—O5—N338.7 (10)C6—C1—C7—N1172.6 (4)
O9—La—O5—N3129.3 (9)C7—N1—C9—C10168.9 (4)
O6—La—O5—N37.2 (5)C7—N1—C9—C1411.1 (6)
O4—La—O5—N369.8 (13)C14—C9—C10—C111.5 (6)
O2—La—O5—N3163.3 (10)N1—C9—C10—C11178.6 (4)
O1—La—O5'—N3153.7 (9)C9—C10—C11—C120.3 (7)
O3—La—O5'—N367.7 (11)C10—C11—C12—C131.5 (7)
O14—La—O5'—N3139.6 (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—C14176.9 (5)
O8—La—O5'—N346.0 (10)C12—C13—C14—C91.1 (7)
O12—La—O5'—N37.9 (13)C10—C9—C14—C130.8 (6)
O9—La—O5'—N392.7 (11)N1—C9—C14—C13179.2 (4)
O6—La—O5'—N314.2 (7)La—O3—C17—C16174.5 (2)
O4—La—O5'—N3101.8 (11)La—O3—C17—C186.2 (4)
O2—La—O5'—N3153.8 (12)C22—C16—C17—O34.4 (5)
O1—La—O6—N328.9 (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—C183.2 (4)
O5'—La—O6—N313.1 (6)C23—O4—C18—C1916.6 (6)
O5—La—O6—N38.0 (5)La—O4—C18—C19172.7 (3)
O11—La—O6—N3135.9 (3)C23—O4—C18—C17163.4 (4)
O8—La—O6—N393.5 (3)La—O4—C18—C177.2 (4)
O12—La—O6—N3161.7 (3)O3—C17—C18—C19178.1 (3)
O9—La—O6—N361.4 (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—O4177.6 (3)
O1—La—O8—N433.1 (3)O4—C18—C19—C20179.8 (3)
O3—La—O8—N4171.8 (2)C17—C18—C19—C200.3 (6)
O14—La—O8—N480.2 (3)C18—C19—C20—C211.2 (6)
O5'—La—O8—N491.4 (5)C19—C20—C21—C160.4 (6)
O5—La—O8—N480.2 (5)C22—C16—C21—C20176.3 (3)
O11—La—O8—N485.5 (3)C17—C16—C21—C201.9 (5)
O12—La—O8—N4136.4 (3)C24—N2—C22—C16175.9 (3)
O9—La—O8—N41.0 (2)C21—C16—C22—N2179.3 (3)
O6—La—O8—N4132.6 (3)C17—C16—C22—N22.5 (5)
O4—La—O8—N4119.8 (2)C22—N2—C24—C25175.6 (4)
O2—La—O8—N425.9 (3)C22—N2—C24—C292.3 (6)
O1—La—O9—N4148.8 (3)C29—C24—C25—C260.4 (7)
O3—La—O9—N417.0 (4)N2—C24—C25—C26178.4 (4)
O14—La—O9—N4144.7 (2)C24—C25—C26—C270.5 (8)
O5'—La—O9—N480.7 (5)C25—C26—C27—C280.1 (8)
O5—La—O9—N479.2 (5)C25—C26—C27—C30179.3 (5)
O11—La—O9—N480.0 (2)C26—C27—C28—C290.7 (9)
O8—La—O9—N41.1 (2)C30—C27—C28—C29179.9 (6)
O12—La—O9—N442.1 (3)C25—C24—C29—C280.2 (8)
O6—La—O9—N439.7 (3)N2—C24—C29—C28177.6 (5)
O4—La—O9—N4114.1 (2)C27—C28—C29—C240.8 (9)
O2—La—O9—N4148.8 (3)
Hydrogen-bond geometry (Å, º) top
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

Experimental details

Crystal data
Chemical formula[La(NO3)3(C15H15NO2)2(CH4O)]
Mr839.54
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.8616 (2), 14.6502 (5), 16.6470 (5)
α, β, γ (°)73.210 (2), 85.648 (2), 79.320 (1)
V3)1803.26 (9)
Z2
Radiation typeMo Kα
µ (mm1)1.26
Crystal size (mm)0.43 × 0.31 × 0.20
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.634, 0.783
No. of measured, independent and
observed [I > 2σ(I)] reflections
30011, 8464, 7465
Rint0.024
(sin θ/λ)max1)0.654
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.101, 1.08
No. of reflections8464
No. of parameters473
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.23, 0.51

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
N1—H1A···O10.862.012.668 (3)132.2
N1—H1A···O110.862.523.307 (4)153.2
N2—H2A···O30.861.952.627 (3)134.8
N2—H2A···O60.862.653.440 (5)153.7
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds