PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m410.
Published online 2008 January 25. doi:  10.1107/S1600536808001955
PMCID: PMC2960405

Diaqua­bis[6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato-κ3 N,N′,O](nitrato-κ2 O,O′)lanthanum(III) monohydrate

Abstract

In the title complex, [La(C11H10N3O2)2(NO3)(H2O)2]·H2O, the La atom is coordinated by four N atoms and six O atoms derived from two 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate ligands, one nitrate anion and two water mol­ecules. The mol­ecules are linked together via hydrogen bonds involving the water mol­ecules, forming a three-dimensional network.

Related literature

For related literature, see: Zhao et al. (2007 [triangle]); Yin et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m410-scheme1.jpg

Experimental

Crystal data

  • [La(C11H10N3O2)2(NO3)(H2O)2]·H2O
  • M r = 687.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m410-efi1.jpg
  • a = 17.396 (2) Å
  • b = 15.0270 (18) Å
  • c = 10.1607 (13) Å
  • β = 94.737 (2)°
  • V = 2647.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.68 mm−1
  • T = 298 (2) K
  • 0.46 × 0.45 × 0.40 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.512, T max = 0.553 (expected range = 0.473–0.510)
  • 13524 measured reflections
  • 4656 independent reflections
  • 3941 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.076
  • S = 1.01
  • 4656 reflections
  • 361 parameters
  • H-atom parameters constrained
  • Δρmax = 0.68 e Å−3
  • Δρmin = −0.55 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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/S1600536808001955/hg2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808001955/hg2369Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (grant No. 20761002). This research was sponsored by the Fund of the Talented Highland Research Programme of Guangxi University (grant No. 205121), the Science Foundation of the State Ethnic Affairs Commission (grant No. 07GX05), the Ministry of Education, Science and Technology Key Projects (grant No. 205121), the Development Foundation of Guangxi Research Institute of Chemical Industry, and the Science Foundation of Guangxi University for Nationalities (grant Nos. 0409032, 0409012, 0509ZD047), People’s Republic of China.

supplementary crystallographic information

Comment

Recently we reported the crystal structures of bis(6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato)zinc(II) trihydrate (Yin et al., 2007) and bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]cobalt(II) 2.5- hydrate (Zhao et al., 2007). As a continuation of these investigations, we report in this paper the crystal structure of Nitrato-diaqua-bis(6-(3,5-dimethyl-1H-pyrazol-1-yl)) picolinato)lanthanum(III) monohydrate.

The asymmetric unit of the title structure consists of the central mononuclear lanthanum(III) complex and one uncoordinated water molecule. The La atom is ten-coordinated by four N atoms and six O atoms derived from two 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinate ligands (DPP), one bidentate nitrate anion and two water molecules that define a pseudotricapped trigonal environment for the lanthanum atom. The angles around La(III) atom range from 47.99 (8) to 144.42 (10)°, the La—O distances range from 2.452 (2) to 2.676 (3) Å, the La—N distances range is from 2.688 (3) to 2.811 (3) Å.

In the crystal structure, the oxygen atoms contribute to the formation of intermolecular hydrogen bonds involving the water molecules; three water molecules and three DDP O atoms form a rings via intermolecular H—O···H hydrogen bonds. A great number of hydrogen contacts link the complex into a three-dimensional network. (Fig. 2; for symmetry codes see Table 2).

Experimental

6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and La(NO3)3. 6H2O were available commercially and were used without further purification. Equimolar 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 217 mg) was dissolved in anhydrous ethyl alcohol (AR,99.9%) (15 ml). The mixture was stirred to give a clear solution, To this solution was added La(NO3)3. 6H2O (0.33 mmol, 144 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, colorless blocks of the title complex were formed. The crystals were isolated, washed with alcohol three times (Yield 75%). Elemental analysis: found: C, 38.24; H, 3.91; N, 14.16%; calc. for C22H26LaN7O10: C, 38.44; H, 3.81; N, 14.26%.

Refinement

H atoms on C atoms were positoned geometrically and refined using a riding model with C—H = 0.96Å and Uiso(H) = 1.2Ueq(C). The water H atoms were located in difference Fourier maps and the O—H distances were constrained 0.85 Å, with Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
The structure of the title compound (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
Fig. 2.
Crystal packing of (I) showing the hydrogen bonded interactions as dashed lines.

Crystal data

[La(C11H10N3O2)2(NO3)(H2O)2]·H2OF000 = 1376
Mr = 687.41Dx = 1.725 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8663 reflections
a = 17.396 (2) Åθ = 2.4–28.3º
b = 15.0270 (18) ŵ = 1.68 mm1
c = 10.1607 (13) ÅT = 298 (2) K
β = 94.737 (2)ºBlock, colorless
V = 2647.0 (6) Å30.46 × 0.45 × 0.40 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer4656 independent reflections
Radiation source: fine-focus sealed tube3941 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.022
T = 298(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −19→20
Tmin = 0.512, Tmax = 0.553k = −17→13
13524 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.077  w = 1/[σ2(Fo2) + (0.0425P)2 + 3.0256P] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4656 reflectionsΔρmax = 0.68 e Å3
361 parametersΔρmin = −0.55 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
La10.725615 (10)−0.033374 (12)0.360394 (18)0.02756 (8)
N10.86114 (15)−0.10885 (18)0.4512 (3)0.0267 (6)
N20.88283 (16)0.0047 (2)0.6034 (3)0.0325 (6)
N30.82454 (16)0.05236 (19)0.5339 (3)0.0342 (7)
N40.59938 (17)0.0651 (2)0.2758 (3)0.0353 (7)
N50.6301 (2)0.0557 (2)0.0593 (3)0.0460 (8)
N60.6814 (2)−0.0130 (3)0.0897 (3)0.0489 (9)
N70.83143 (19)0.0967 (2)0.2242 (4)0.0497 (9)
O10.75996 (14)−0.17799 (17)0.2701 (3)0.0428 (6)
O20.83910 (15)−0.28912 (17)0.2271 (3)0.0442 (6)
O30.64201 (14)0.02652 (17)0.5260 (3)0.0391 (6)
O40.53914 (16)0.0940 (2)0.5969 (3)0.0562 (8)
O50.76750 (16)0.12248 (19)0.2609 (3)0.0500 (7)
O60.84704 (16)0.01423 (19)0.2392 (3)0.0479 (7)
O70.87668 (19)0.1474 (3)0.1778 (5)0.0911 (14)
O80.60430 (15)−0.13605 (19)0.3366 (3)0.0529 (8)
H8B0.5958−0.15490.25780.064*
H8C0.5645−0.10900.35900.064*
O90.72302 (15)−0.12026 (18)0.5879 (3)0.0466 (7)
H9B0.7684−0.13520.61670.056*
H9C0.6957−0.16700.57730.056*
O100.6289 (2)0.7859 (2)0.0804 (4)0.0771 (10)
H10C0.63330.83330.12600.093*
H10D0.66850.75440.10170.093*
C10.8231 (2)−0.2207 (2)0.2862 (3)0.0329 (8)
C20.88316 (19)−0.1827 (2)0.3894 (3)0.0303 (7)
C30.9541 (2)−0.2219 (3)0.4173 (4)0.0423 (9)
H30.9677−0.27310.37330.051*
C41.0046 (2)−0.1830 (2)0.5129 (4)0.0458 (10)
H41.0528−0.20820.53400.055*
C50.9835 (2)−0.1071 (3)0.5771 (4)0.0394 (9)
H51.0172−0.07980.64060.047*
C60.91020 (18)−0.0727 (2)0.5436 (3)0.0293 (7)
C70.9641 (3)0.0119 (4)0.8243 (5)0.0706 (15)
H7A1.01500.02090.79710.106*
H7B0.9554−0.05050.83670.106*
H7C0.95900.04280.90580.106*
C80.9060 (2)0.0469 (3)0.7204 (4)0.0434 (9)
C90.8629 (2)0.1226 (3)0.7219 (4)0.0497 (10)
H90.86570.16540.78820.060*
C100.8133 (2)0.1242 (3)0.6055 (4)0.0401 (9)
C110.7556 (3)0.1936 (3)0.5615 (5)0.0584 (12)
H11A0.73760.18340.47090.088*
H11B0.77920.25130.56990.088*
H11C0.71290.19090.61540.088*
C120.5787 (2)0.0682 (3)0.5086 (4)0.0376 (8)
C130.5506 (2)0.0867 (2)0.3666 (4)0.0387 (9)
C140.4786 (2)0.1229 (3)0.3322 (5)0.0543 (11)
H140.44700.14010.39710.065*
C150.4546 (3)0.1331 (3)0.2014 (5)0.0624 (13)
H150.40580.15580.17660.075*
C160.5029 (2)0.1095 (3)0.1070 (5)0.0558 (11)
H160.48710.11430.01750.067*
C170.5761 (2)0.0784 (3)0.1492 (4)0.0417 (9)
C180.6004 (3)0.1738 (3)−0.1168 (5)0.0749 (16)
H18A0.63310.2046−0.17330.112*
H18B0.58840.2124−0.04600.112*
H18C0.55360.1564−0.16680.112*
C190.6413 (3)0.0926 (3)−0.0609 (4)0.0540 (11)
C200.6981 (3)0.0444 (3)−0.1085 (5)0.0657 (14)
H200.71790.0526−0.18980.079*
C210.7219 (3)−0.0198 (3)−0.0151 (4)0.0567 (12)
C220.7836 (3)−0.0884 (4)−0.0240 (5)0.0836 (17)
H22A0.8261−0.07520.03940.125*
H22B0.8010−0.0879−0.11120.125*
H22C0.7633−0.1461−0.00580.125*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
La10.02153 (12)0.03166 (13)0.02925 (12)0.00294 (8)0.00059 (8)−0.00108 (8)
N10.0216 (14)0.0310 (15)0.0276 (14)0.0017 (11)0.0031 (11)0.0041 (12)
N20.0269 (15)0.0347 (15)0.0346 (16)−0.0006 (12)−0.0041 (12)−0.0010 (13)
N30.0275 (15)0.0330 (16)0.0408 (17)0.0017 (12)−0.0058 (13)−0.0021 (13)
N40.0287 (16)0.0377 (16)0.0386 (17)0.0042 (13)−0.0018 (13)0.0012 (13)
N50.046 (2)0.057 (2)0.0322 (17)0.0051 (16)−0.0084 (15)0.0046 (15)
N60.046 (2)0.068 (2)0.0322 (17)0.0118 (17)0.0012 (15)0.0004 (16)
N70.0322 (18)0.055 (2)0.060 (2)−0.0042 (16)−0.0058 (16)0.0234 (18)
O10.0303 (14)0.0451 (16)0.0511 (16)0.0081 (11)−0.0078 (11)−0.0149 (12)
O20.0428 (15)0.0388 (15)0.0513 (16)0.0042 (12)0.0063 (12)−0.0164 (13)
O30.0309 (14)0.0502 (16)0.0362 (14)0.0111 (11)0.0028 (11)−0.0030 (11)
O40.0382 (16)0.074 (2)0.0579 (18)0.0116 (14)0.0128 (14)−0.0184 (16)
O50.0420 (16)0.0489 (17)0.0589 (18)0.0097 (13)0.0025 (13)0.0137 (14)
O60.0377 (15)0.0482 (18)0.0587 (18)0.0069 (12)0.0092 (13)0.0159 (14)
O70.0435 (19)0.080 (3)0.150 (4)−0.0069 (18)0.011 (2)0.064 (3)
O80.0298 (14)0.0544 (18)0.076 (2)−0.0034 (12)0.0101 (13)−0.0254 (15)
O90.0365 (15)0.0539 (17)0.0491 (16)0.0021 (12)0.0020 (12)0.0141 (13)
O100.071 (2)0.065 (2)0.092 (3)0.0011 (18)−0.013 (2)−0.0078 (19)
C10.0314 (19)0.035 (2)0.0331 (19)−0.0008 (15)0.0071 (15)−0.0003 (16)
C20.0265 (17)0.0276 (18)0.0375 (19)0.0006 (13)0.0066 (14)0.0032 (14)
C30.031 (2)0.037 (2)0.058 (3)0.0095 (16)0.0051 (18)−0.0014 (18)
C40.0286 (19)0.044 (2)0.064 (3)0.0105 (17)−0.0001 (18)0.005 (2)
C50.0275 (18)0.043 (2)0.047 (2)−0.0014 (16)−0.0042 (16)0.0060 (17)
C60.0243 (17)0.0311 (18)0.0324 (18)−0.0037 (14)0.0020 (14)0.0044 (14)
C70.058 (3)0.110 (4)0.040 (2)0.013 (3)−0.016 (2)−0.010 (3)
C80.034 (2)0.061 (3)0.035 (2)0.0005 (18)−0.0042 (16)−0.0093 (18)
C90.044 (2)0.058 (3)0.046 (2)−0.002 (2)−0.0007 (19)−0.025 (2)
C100.034 (2)0.039 (2)0.047 (2)−0.0022 (16)0.0020 (17)−0.0086 (17)
C110.055 (3)0.041 (2)0.077 (3)0.009 (2)−0.006 (2)−0.021 (2)
C120.030 (2)0.037 (2)0.046 (2)0.0014 (16)0.0061 (17)−0.0076 (17)
C130.0272 (18)0.036 (2)0.052 (2)0.0031 (15)−0.0005 (16)−0.0022 (17)
C140.035 (2)0.056 (3)0.072 (3)0.0158 (19)0.004 (2)0.004 (2)
C150.034 (2)0.071 (3)0.080 (3)0.019 (2)−0.010 (2)0.015 (3)
C160.044 (2)0.064 (3)0.055 (3)0.008 (2)−0.017 (2)0.012 (2)
C170.038 (2)0.044 (2)0.042 (2)0.0004 (17)−0.0060 (17)0.0018 (17)
C180.101 (4)0.068 (3)0.052 (3)−0.006 (3)−0.013 (3)0.016 (3)
C190.066 (3)0.060 (3)0.034 (2)−0.008 (2)−0.005 (2)0.000 (2)
C200.086 (4)0.078 (4)0.034 (2)−0.013 (3)0.007 (2)0.002 (2)
C210.063 (3)0.071 (3)0.037 (2)0.003 (2)0.009 (2)−0.012 (2)
C220.087 (4)0.107 (5)0.061 (3)0.023 (4)0.028 (3)−0.005 (3)

Geometric parameters (Å, °)

La1—O12.452 (2)C3—C41.384 (5)
La1—O32.482 (2)C3—H30.9300
La1—O82.609 (3)C4—C51.379 (5)
La1—O62.630 (3)C4—H40.9300
La1—O92.659 (3)C5—C61.392 (5)
La1—O52.676 (3)C5—H50.9300
La1—N32.688 (3)C7—C81.495 (6)
La1—N12.709 (3)C7—H7A0.9600
La1—N42.727 (3)C7—H7B0.9600
La1—N62.811 (3)C7—H7C0.9600
N1—C61.331 (4)C8—C91.363 (6)
N1—C21.347 (4)C9—C101.405 (5)
N2—C81.378 (5)C9—H90.9300
N2—N31.386 (4)C10—C111.491 (6)
N2—C61.413 (5)C11—H11A0.9600
N3—C101.325 (5)C11—H11B0.9600
N4—C171.331 (5)C11—H11C0.9600
N4—C131.344 (5)C12—C131.510 (5)
N5—C191.369 (5)C13—C141.383 (5)
N5—N61.382 (5)C14—C151.369 (7)
N5—C171.406 (5)C14—H140.9300
N6—C211.329 (6)C15—C161.373 (7)
N7—O71.218 (4)C15—H150.9300
N7—O51.263 (4)C16—C171.392 (5)
N7—O61.275 (4)C16—H160.9300
O1—C11.271 (4)C18—C191.501 (7)
O2—C11.234 (4)C18—H18A0.9600
O3—C121.266 (4)C18—H18B0.9600
O4—C121.238 (4)C18—H18C0.9600
O8—H8B0.8499C19—C201.346 (7)
O8—H8C0.8500C20—C211.393 (7)
O9—H9B0.8500C20—H200.9300
O9—H9C0.8499C21—C221.496 (7)
O10—H10C0.8501C22—H22A0.9600
O10—H10D0.8499C22—H22B0.9600
C1—C21.528 (5)C22—H22C0.9600
C2—C31.375 (5)
O1—La1—O3138.56 (9)O2—C1—C2118.4 (3)
O1—La1—O870.21 (8)O1—C1—C2115.8 (3)
O3—La1—O876.27 (9)N1—C2—C3122.8 (3)
O1—La1—O680.56 (9)N1—C2—C1115.0 (3)
O3—La1—O6139.19 (9)C3—C2—C1122.2 (3)
O8—La1—O6142.37 (9)C2—C3—C4118.1 (4)
O1—La1—O984.97 (9)C2—C3—H3121.0
O3—La1—O962.33 (8)C4—C3—H3121.0
O8—La1—O973.66 (9)C5—C4—C3120.3 (3)
O6—La1—O9127.78 (8)C5—C4—H4119.9
O1—La1—O5123.50 (10)C3—C4—H4119.9
O3—La1—O597.58 (9)C4—C5—C6117.7 (3)
O8—La1—O5136.54 (9)C4—C5—H5121.1
O6—La1—O547.99 (8)C6—C5—H5121.1
O9—La1—O5141.55 (9)N1—C6—C5122.8 (3)
O1—La1—N3120.50 (8)N1—C6—N2114.8 (3)
O3—La1—N376.17 (9)C5—C6—N2122.3 (3)
O8—La1—N3144.42 (10)C8—C7—H7A109.5
O6—La1—N371.41 (10)C8—C7—H7B109.5
O9—La1—N373.81 (9)H7A—C7—H7B109.5
O5—La1—N369.44 (9)C8—C7—H7C109.5
O1—La1—N161.59 (8)H7A—C7—H7C109.5
O3—La1—N1117.58 (8)H7B—C7—H7C109.5
O8—La1—N1117.29 (9)C9—C8—N2105.7 (3)
O6—La1—N164.12 (8)C9—C8—C7128.8 (4)
O9—La1—N164.84 (8)N2—C8—C7125.4 (4)
O5—La1—N1103.81 (8)C8—C9—C10107.8 (3)
N3—La1—N159.02 (8)C8—C9—H9126.1
O1—La1—N4125.28 (8)C10—C9—H9126.1
O3—La1—N461.02 (9)N3—C10—C9109.9 (3)
O8—La1—N470.58 (9)N3—C10—C11122.1 (3)
O6—La1—N4111.20 (9)C9—C10—C11128.0 (4)
O9—La1—N4118.00 (9)C10—C11—H11A109.5
O5—La1—N469.10 (9)C10—C11—H11B109.5
N3—La1—N4113.69 (9)H11A—C11—H11B109.5
N1—La1—N4171.90 (9)C10—C11—H11C109.5
O1—La1—N677.64 (10)H11A—C11—H11C109.5
O3—La1—N6119.69 (9)H11B—C11—H11C109.5
O8—La1—N679.60 (11)O4—C12—O3125.6 (4)
O6—La1—N671.22 (10)O4—C12—C13118.7 (3)
O9—La1—N6151.80 (10)O3—C12—C13115.7 (3)
O5—La1—N666.17 (10)N4—C13—C14122.1 (4)
N3—La1—N6134.28 (10)N4—C13—C12116.0 (3)
N1—La1—N6122.64 (9)C14—C13—C12121.9 (4)
N4—La1—N658.94 (9)C15—C14—C13119.1 (4)
C6—N1—C2118.3 (3)C15—C14—H14120.4
C6—N1—La1124.0 (2)C13—C14—H14120.4
C2—N1—La1117.3 (2)C14—C15—C16119.6 (4)
C8—N2—N3110.6 (3)C14—C15—H15120.2
C8—N2—C6131.7 (3)C16—C15—H15120.2
N3—N2—C6117.7 (3)C15—C16—C17118.0 (4)
C10—N3—N2106.0 (3)C15—C16—H16121.0
C10—N3—La1129.4 (2)C17—C16—H16121.0
N2—N3—La1119.2 (2)N4—C17—C16123.1 (4)
C17—N4—C13117.9 (3)N4—C17—N5115.2 (3)
C17—N4—La1124.0 (2)C16—C17—N5121.7 (4)
C13—N4—La1116.9 (2)C19—C18—H18A109.5
C19—N5—N6111.5 (4)C19—C18—H18B109.5
C19—N5—C17129.2 (4)H18A—C18—H18B109.5
N6—N5—C17119.3 (3)C19—C18—H18C109.5
C21—N6—N5104.7 (3)H18A—C18—H18C109.5
C21—N6—La1130.9 (3)H18B—C18—H18C109.5
N5—N6—La1114.8 (2)C20—C19—N5105.4 (4)
O7—N7—O5122.4 (4)C20—C19—C18129.8 (4)
O7—N7—O6121.1 (4)N5—C19—C18124.7 (4)
O5—N7—O6116.5 (3)C19—C20—C21108.3 (4)
C1—O1—La1129.3 (2)C19—C20—H20125.9
C12—O3—La1129.5 (2)C21—C20—H20125.9
N7—O5—La196.7 (2)N6—C21—C20110.2 (4)
N7—O6—La198.6 (2)N6—C21—C22122.2 (4)
La1—O8—H8B111.1C20—C21—C22127.7 (5)
La1—O8—H8C111.3C21—C22—H22A109.5
H8B—O8—H8C109.2C21—C22—H22B109.5
La1—O9—H9B110.3H22A—C22—H22B109.5
La1—O9—H9C110.2C21—C22—H22C109.5
H9B—O9—H9C108.6H22A—C22—H22C109.5
H10C—O10—H10D107.0H22B—C22—H22C109.5
O2—C1—O1125.8 (3)
O1—La1—N1—C6−179.1 (3)N4—La1—O3—C125.2 (3)
O3—La1—N1—C6−46.4 (3)N6—La1—O3—C12−0.6 (3)
O8—La1—N1—C6−134.5 (2)O7—N7—O5—La1−175.3 (4)
O6—La1—N1—C687.7 (3)O6—N7—O5—La14.1 (3)
O9—La1—N1—C6−80.9 (2)O1—La1—O5—N7−33.0 (3)
O5—La1—N1—C660.0 (3)O3—La1—O5—N7152.8 (2)
N3—La1—N1—C64.7 (2)O8—La1—O5—N7−129.2 (2)
N4—La1—N1—C631.5 (7)O6—La1—O5—N7−2.4 (2)
N6—La1—N1—C6130.3 (2)O9—La1—O5—N798.7 (2)
O1—La1—N1—C27.7 (2)N3—La1—O5—N780.7 (2)
O3—La1—N1—C2140.5 (2)N1—La1—O5—N731.9 (2)
O8—La1—N1—C252.3 (2)N4—La1—O5—N7−152.2 (2)
O6—La1—N1—C2−85.4 (2)N6—La1—O5—N7−88.0 (2)
O9—La1—N1—C2106.0 (2)O7—N7—O6—La1175.2 (4)
O5—La1—N1—C2−113.1 (2)O5—N7—O6—La1−4.2 (4)
N3—La1—N1—C2−168.4 (3)O1—La1—O6—N7156.9 (2)
N4—La1—N1—C2−141.6 (6)O3—La1—O6—N7−37.2 (3)
N6—La1—N1—C2−42.8 (3)O8—La1—O6—N7117.9 (2)
C8—N2—N3—C101.6 (4)O9—La1—O6—N7−127.1 (2)
C6—N2—N3—C10−175.5 (3)O5—La1—O6—N72.4 (2)
C8—N2—N3—La1−155.0 (3)N3—La1—O6—N7−76.3 (2)
C6—N2—N3—La127.9 (4)N1—La1—O6—N7−140.2 (2)
O1—La1—N3—C10−170.6 (3)N4—La1—O6—N732.6 (2)
O3—La1—N3—C10−31.9 (3)N6—La1—O6—N776.8 (2)
O8—La1—N3—C10−72.1 (4)La1—O1—C1—O2−172.2 (3)
O6—La1—N3—C10122.9 (3)La1—O1—C1—C28.3 (5)
O9—La1—N3—C10−96.7 (3)C6—N1—C2—C3−0.3 (5)
O5—La1—N3—C1071.8 (3)La1—N1—C2—C3173.2 (3)
N1—La1—N3—C10−166.7 (4)C6—N1—C2—C1179.2 (3)
N4—La1—N3—C1017.3 (3)La1—N1—C2—C1−7.3 (4)
N6—La1—N3—C1086.3 (3)O2—C1—C2—N1−179.0 (3)
O1—La1—N3—N2−20.2 (3)O1—C1—C2—N10.6 (4)
O3—La1—N3—N2118.4 (3)O2—C1—C2—C30.4 (5)
O8—La1—N3—N278.3 (3)O1—C1—C2—C3−180.0 (3)
O6—La1—N3—N2−86.7 (2)N1—C2—C3—C4−0.2 (6)
O9—La1—N3—N253.7 (2)C1—C2—C3—C4−179.6 (3)
O5—La1—N3—N2−137.8 (3)C2—C3—C4—C5−0.2 (6)
N1—La1—N3—N2−16.3 (2)C3—C4—C5—C61.0 (6)
N4—La1—N3—N2167.7 (2)C2—N1—C6—C51.2 (5)
N6—La1—N3—N2−123.4 (2)La1—N1—C6—C5−171.9 (3)
O1—La1—N4—C17−44.0 (3)C2—N1—C6—N2179.8 (3)
O3—La1—N4—C17−175.1 (3)La1—N1—C6—N26.8 (4)
O8—La1—N4—C17−90.4 (3)C4—C5—C6—N1−1.5 (5)
O6—La1—N4—C1749.4 (3)C4—C5—C6—N2179.9 (3)
O9—La1—N4—C17−148.8 (3)C8—N2—C6—N1161.2 (4)
O5—La1—N4—C1773.0 (3)N3—N2—C6—N1−22.4 (4)
N3—La1—N4—C17127.6 (3)C8—N2—C6—C5−20.2 (6)
N1—La1—N4—C17102.6 (6)N3—N2—C6—C5156.2 (3)
N6—La1—N4—C17−1.1 (3)N3—N2—C8—C9−1.4 (4)
O1—La1—N4—C13123.1 (3)C6—N2—C8—C9175.2 (4)
O3—La1—N4—C13−8.1 (2)N3—N2—C8—C7175.9 (4)
O8—La1—N4—C1376.6 (3)C6—N2—C8—C7−7.5 (7)
O6—La1—N4—C13−143.6 (3)N2—C8—C9—C100.7 (5)
O9—La1—N4—C1318.3 (3)C7—C8—C9—C10−176.5 (5)
O5—La1—N4—C13−120.0 (3)N2—N3—C10—C9−1.1 (4)
N3—La1—N4—C13−65.3 (3)La1—N3—C10—C9152.2 (3)
N1—La1—N4—C13−90.3 (6)N2—N3—C10—C11178.7 (4)
N6—La1—N4—C13166.0 (3)La1—N3—C10—C11−28.0 (6)
C19—N5—N6—C21−2.3 (5)C8—C9—C10—N30.3 (5)
C17—N5—N6—C21177.8 (4)C8—C9—C10—C11−179.5 (4)
C19—N5—N6—La1147.9 (3)La1—O3—C12—O4177.9 (3)
C17—N5—N6—La1−32.0 (4)La1—O3—C12—C13−1.9 (5)
O1—La1—N6—C21−58.1 (4)C17—N4—C13—C14−0.9 (6)
O3—La1—N6—C21162.6 (4)La1—N4—C13—C14−168.8 (3)
O8—La1—N6—C21−129.9 (4)C17—N4—C13—C12178.5 (3)
O6—La1—N6—C2126.0 (4)La1—N4—C13—C1210.6 (4)
O9—La1—N6—C21−111.3 (4)O4—C12—C13—N4173.7 (4)
O5—La1—N6—C2177.5 (4)O3—C12—C13—N4−6.5 (5)
N3—La1—N6—C2162.7 (4)O4—C12—C13—C14−7.0 (6)
N1—La1—N6—C21−14.1 (5)O3—C12—C13—C14172.9 (4)
N4—La1—N6—C21156.6 (4)N4—C13—C14—C153.3 (7)
O1—La1—N6—N5161.5 (3)C12—C13—C14—C15−176.0 (4)
O3—La1—N6—N522.2 (3)C13—C14—C15—C16−1.8 (7)
O8—La1—N6—N589.7 (3)C14—C15—C16—C17−1.9 (7)
O6—La1—N6—N5−114.4 (3)C13—N4—C17—C16−3.1 (6)
O9—La1—N6—N5108.3 (3)La1—N4—C17—C16163.9 (3)
O5—La1—N6—N5−62.9 (3)C13—N4—C17—N5179.1 (3)
N3—La1—N6—N5−77.7 (3)La1—N4—C17—N5−13.9 (5)
N1—La1—N6—N5−154.5 (2)C15—C16—C17—N44.5 (7)
N4—La1—N6—N516.2 (3)C15—C16—C17—N5−177.9 (4)
O3—La1—O1—C1−109.3 (3)C19—N5—C17—N4−148.7 (4)
O8—La1—O1—C1−147.2 (3)N6—N5—C17—N431.1 (5)
O6—La1—O1—C156.9 (3)C19—N5—C17—C1633.4 (7)
O9—La1—O1—C1−72.8 (3)N6—N5—C17—C16−146.7 (4)
O5—La1—O1—C179.4 (3)N6—N5—C19—C202.3 (5)
N3—La1—O1—C1−4.9 (3)C17—N5—C19—C20−177.8 (4)
N1—La1—O1—C1−8.7 (3)N6—N5—C19—C18−173.9 (4)
N4—La1—O1—C1166.2 (3)C17—N5—C19—C186.0 (7)
N6—La1—O1—C1129.6 (3)N5—C19—C20—C21−1.4 (5)
O1—La1—O3—C12−106.5 (3)C18—C19—C20—C21174.5 (5)
O8—La1—O3—C12−70.0 (3)N5—N6—C21—C201.3 (5)
O6—La1—O3—C1294.7 (3)La1—N6—C21—C20−141.9 (4)
O9—La1—O3—C12−148.5 (3)N5—N6—C21—C22−178.8 (5)
O5—La1—O3—C1266.2 (3)La1—N6—C21—C2237.9 (7)
N3—La1—O3—C12132.8 (3)C19—C20—C21—N60.0 (6)
N1—La1—O3—C12176.2 (3)C19—C20—C21—C22−179.8 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O8—H8B···O10i0.852.132.918 (5)154
O8—H8C···O4ii0.851.912.713 (4)158
O9—H9B···O2iii0.851.962.731 (4)151
O9—H9B···N10.852.462.878 (4)112
O10—H10C···N6iv0.852.493.156 (5)136
O10—H10D···O9v0.852.242.977 (5)146
O10—H10D···O1iv0.852.462.913 (4)114

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2369).

References

  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yin, X.-H., Zhao, K., Feng, Y. & Zhu, J. (2007). Acta Cryst. E63, m2926.
  • Zhao, K., Yin, X.-H., Feng, Y. & Zhu, J. (2007). Acta Cryst. E63, m3024.

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