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The title compound, (C12H9N2)3[Y(C7H3NO4)3]·C2H6OS·5H2O or (phenH)3[Y(pydc)3]·DMSO·5H2O (phenH is 1,10-phenanthrolinium, pydc is pyridine-2,6-dicarboxyl­ate and DMSO is dimethyl sulfoxide), was synthesized by the reaction of YCl3 with the proton-transfer compound (phenH)2(pydc) in DMSO as solvent. The nine donor atoms of the three pydc2− fragments form a distorted tricapped trigonal–prismatic arrangement around the YIII centre. Considerable π–π and C—H...π stacking inter­actions between the aromatic rings of pydc2− [centroid–centroid distances 3.659 (4) and 3.662 (4) Å], and between the CH groups of DMSO with the benzene rings of the pydc2− fragments, are observed. In the crystal structure, a wide range of non-covalent inter­actions consisting of hydrogen bonding [of the types O—H...O, O—H...S, N—H...O and C—H...O], ion pairing, π–π and C—H...π stacking connect the various components into a supra­molecular structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060047/om2178sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060047/om2178Isup2.hkl
Contains datablock I

CCDC reference: 649971

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.054
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H16A .. H17A .. 2.02 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg. PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C8 - C9 ... 1.53 Ang. PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CG1 (N3 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C21 H9 N3 O12 Y PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C12 H9 N2 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 6 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 7 H2 O PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 9 H2 O
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.59 From the CIF: _reflns_number_total 11832 Count of symmetry unique reflns 6446 Completeness (_total/calc) 183.56% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 5386 Fraction of Friedel pairs measured 0.836 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Just as there is a field of molecular chemistry based on the covalent bond, there is a field of supramolecular chemistry, the chemistry of molecular assemblies and of the intermolecular bond. The non-covalent interactions such as ion pairing, hydrogen bonding and ππ stacking are observed in these ionic compounds. The importance of weak hydrogen bonds in the context of crystal engineering, molecular recognition and supramolecular chemistry has been well recognized in recent years. Recently, we have defined a plan to prepare water soluble proton transfer compounds as novel self-assembled systems that can function as suitable ligands in the synthesis of metal complexes. In this regard, we have reported cases in which proton transfer from pyridine-2,6-dicarboxylic acid, pydcH2, and benzene-1,2,4,5-tetracarboxylicacid, btcH4, to propane-1,3-diamine (pn) and 1,10-phenanthroline, (phen), results in the formation of self-assembled (pnH2)(pydc).(pydcH2)·2.5H2O, (pnH2)2(btc)·2H2O and (phenH)4(btcH3)2(btcH2) systems, respectively. Our attempts to obtain single crystals of the proton transfer compound (phenH)2(pydc) were not successful. The resulting compounds with some remaining sites as electron donors can coordinate to metal ions (Aghabozorg, Attar Gharamaleki Ghadermazi et al., 2007; Aghabozorg, Attar Gharamaleki, Ghasemikhah et al., 2007; Aghabozorg, Daneshvar et al., 2007, and references therein).

The molecular structure of the anion of the title compound, (phenH)3[Y(pydc)3].DMSO.5H2O is presented in Fig. 1, while its disposition with respect to the remaining constituents is illustrated in Fig. 2. Bond lengths and angles are presented in Table 1. Fig. 3 presents the hydrogen bonding between its components. Also hydrogen bond lengths are given separately in Table 2.

In the structure, YIII is coordinated by three pydc2- groups as tridentate ligands, and a nine coordinate complex results. For balancing the charge, three protonated 1,10-phenanthrolines, (phenH)+, exist.

The sum of the bond angles, N1—Y1—N2, N1—Y1—N3 and N2—Y1—N3 equals to 359.94° and indicates that YIII is located in the center of N1N2N3 plane. The three O atoms O1, O8 and O12 form a triangle and the other three, O4, O5 and O9 form another triangle around the YIII. Considering the angles between the oxygen atoms, a prismatic geometry consisting of the six O atoms and three nitrogen caps on its faces is proposed (Fig. 4). This anion has been previously reported to have a tricapped prismatic geometry (Tancrez et al., 2005; Brayshaw, et al., 2005).

In the structure of the (phenH)3[Y(pydc)3]·DMSO·5H2O complex, the spaces between two layers of [Y(pydc)3]3– anions are filled with (phenH)+ cations, DMSO and water molecules (Fig. 5). A noticeable feature of the title compound is the presence of a C–H···π stacking interactions between a C—H group of DMSO molecules with an aromatic ring of a pydc2- unit. The C—H···π distance (measured to the centre of phenyl ring) is 2.84 Å for C58—H58C···Cg(1) (1 + x, y, z) with the angles of 119°, [Cg(1) is the centroid of N3,C16—C20] (Fig. 6). Also a considerable π-π stacking interactions between aromatic rings of pyridine-2,6-dicarboxylate fragments with distances of 3.659 (4) Å for X1B···X1A (x, y, z) and 3.662 (4) Å for X1A···X1C (1 + x, -1 + y, 1 + z) are observed (Fig. 7). A wide range of non-covalent interactions consisting of hydrogen bonding (of the type O—H···O, O—H···S, N—H···O and C—H···O with D···A ranging from 2.612 (6) Å to 3.650 (4) Å, ion pairing, ππ and C—H···π stacking connect the various components into a supramolecular structure (Table 2, Fig. 2 and Fig. 3).

Related literature top

For related literature, see: Aghabozorg, Attar Gharamaleki, Ghadermazi et al. (2007); Aghabozorg, Attar Gharamaleki, Ghasemikhah et al. (2007); Aghabozorg, Daneshvar et al. (2007); Brayshaw et al. (2005); Tancrez et al. (2005).

Experimental top

The proton transfer compound of (phenH)2(pydc) was prepared according to our reported procedure. A solution of YCl3 (0.05 mmol, 11 mg) in dimethylsulfoxide (DMSO) (5 ml) was added to a stirring solution of (phenH)2(pydc) (0.095 mmol, 50 mg) in DMSO (5 ml). The volume of the resulting suspension was increased by adding 5 ml H2O at room temperature. Due to the high viscosity of DMSO solvent, the crystallization time for the title complex was very long, so that it took about nine months for the colorless crystals to be obtained from the solution.

Refinement top

Hydrogen atoms were positioned geometrically and refined with a riding model (including torsional freedom for methyl groups), with C—H = 0.95–0.98 Å, and with U(H) constrained to be 1.2 (1.5 for methyl groups) times Ueq of the carrier atom. Hydrogen atoms on phen were initially found in a difference Fourier map and placed with no ambiguity.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The structure of the anion of the title compound showing the atom-numbering scheme and displacement ellipsoids at the 50% probability level.
[Figure 2] Fig. 2. The anion, cations, DMSO and water molecules with their atom numbering and thermal ellipsoids at the 50% probability level are shown.
[Figure 3] Fig. 3. The hydrogen bonding between different components of the title compound.
[Figure 4] Fig. 4. Coordination environment of the central Y atom.
[Figure 5] Fig. 5. A packing diagram as viewed down the a axis. The space between the two layers of [Y(pydc)3]3– fragments is filled with a layer of (phenH)+ cations, DMSO and water molecules.
[Figure 6] Fig. 6. C–H···π stacking interactions between C—H groups of DMSO with aromatic rings of pydc2- units. The C—H···π distances (measured to the centre of phenyl ring) are 2.840 Å for C58—H58C···Cg(1) (1 + x, y, z) with the angles of 119° [Cg(1) is the centroid of N3,C16—C20]
[Figure 7] Fig. 7. π-π stacking interactions between aromatic rings of pyridine-2,6-dicarboxylate fragments with distances of 3.659 (4) Å for X1B···X1A (x, y, z) and 3.662 (4) Å for X1A···X1C (1 + x, -1 + y, 1 + z).
Tris(1,10-phenanthrolinium) tris(pyridine-2,6-dicarboxylato)yttriumate dimethyl sulfoxide pentahydrate top
Crystal data top
(C12H9N2)3[Y(C7H3NO4)3]·C2H6OS·5H2OZ = 1
Mr = 1296.08F(000) = 668
Triclinic, P1Dx = 1.554 Mg m3
a = 10.4185 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.9689 (14) ÅCell parameters from 5015 reflections
c = 14.3844 (19) Åθ = 2.2–26.9°
α = 70.599 (2)°µ = 1.18 mm1
β = 81.174 (2)°T = 150 K
γ = 63.298 (2)°Block, colourless
V = 1385.1 (3) Å30.30 × 0.20 × 0.17 mm
Data collection top
Bruker SMART 1000
diffractometer
11832 independent reflections
Radiation source: fine-focus sealed tube8989 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.045
Detector resolution: 8.3 pixels mm-1θmax = 27.6°, θmin = 1.5°
ω scansh = 1313
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1414
Tmin = 0.719, Tmax = 0.825l = 1818
15984 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0623P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
11832 reflectionsΔρmax = 0.70 e Å3
795 parametersΔρmin = 0.85 e Å3
3 restraintsAbsolute structure: Flack (1983), 5621 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (4)
Crystal data top
(C12H9N2)3[Y(C7H3NO4)3]·C2H6OS·5H2Oγ = 63.298 (2)°
Mr = 1296.08V = 1385.1 (3) Å3
Triclinic, P1Z = 1
a = 10.4185 (14) ÅMo Kα radiation
b = 10.9689 (14) ŵ = 1.18 mm1
c = 14.3844 (19) ÅT = 150 K
α = 70.599 (2)°0.30 × 0.20 × 0.17 mm
β = 81.174 (2)°
Data collection top
Bruker SMART 1000
diffractometer
11832 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
8989 reflections with I > 2σ(I)
Tmin = 0.719, Tmax = 0.825Rint = 0.045
15984 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.131Δρmax = 0.70 e Å3
S = 1.00Δρmin = 0.85 e Å3
11832 reflectionsAbsolute structure: Flack (1983), 5621 Friedel pairs
795 parametersAbsolute structure parameter: 0.004 (4)
3 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Y10.11333 (4)1.34289 (4)0.10288 (3)0.01762 (11)
S10.57322 (16)0.90591 (15)0.26814 (10)0.0275 (3)
C10.1728 (5)1.2743 (5)0.0431 (4)0.0211 (11)
C20.2177 (5)1.3214 (5)0.0298 (3)0.0201 (10)
C30.3466 (5)1.3313 (5)0.0244 (3)0.0233 (11)
H30.41661.30180.02390.028*
C40.3713 (6)1.3855 (6)0.0914 (4)0.0285 (13)
H40.45821.39500.08830.034*
C50.2700 (6)1.4250 (6)0.1616 (4)0.0267 (11)
H50.28491.46280.20750.032*
C60.1447 (5)1.4084 (5)0.1641 (3)0.0191 (10)
C70.0253 (6)1.4468 (5)0.2388 (4)0.0210 (12)
C80.4004 (6)1.3917 (6)0.2435 (4)0.0210 (12)
C90.4383 (5)1.5452 (5)0.1780 (3)0.0200 (10)
C100.5669 (6)1.6627 (6)0.1831 (4)0.0257 (11)
H100.63921.65180.22960.031*
C110.5869 (5)1.7963 (6)0.1186 (4)0.0258 (12)
H110.67401.87800.11980.031*
C120.4786 (6)1.8093 (5)0.0525 (3)0.0253 (11)
H120.48951.90030.00920.030*
C130.3546 (5)1.6882 (5)0.0505 (3)0.0208 (10)
C140.2305 (5)1.6851 (5)0.0200 (3)0.0171 (10)
C150.0479 (5)1.0031 (5)0.2240 (4)0.0191 (11)
C160.0399 (5)0.9977 (5)0.1514 (3)0.0197 (10)
C170.0407 (5)0.8733 (5)0.1476 (4)0.0249 (11)
H170.01580.78330.19200.030*
C180.1265 (6)0.8829 (6)0.0769 (4)0.0315 (13)
H180.13050.79970.07350.038*
C190.2050 (6)1.0148 (5)0.0123 (4)0.0239 (11)
H190.26051.02330.03810.029*
C200.2014 (5)1.1354 (5)0.0223 (3)0.0182 (10)
C210.2849 (5)1.2869 (5)0.0419 (4)0.0195 (11)
C220.0197 (6)1.6003 (6)0.2235 (4)0.0274 (12)
H220.00151.54350.15680.033*
C230.0303 (6)1.5373 (6)0.2976 (4)0.0300 (12)
H230.08651.43690.28200.036*
C240.0000 (6)1.6179 (6)0.3936 (4)0.0271 (11)
H240.03491.57340.44450.033*
C250.0831 (5)1.7670 (6)0.4174 (4)0.0240 (11)
C260.1224 (5)1.8588 (6)0.5159 (4)0.0250 (11)
H260.09431.81870.56910.030*
C270.1994 (6)2.0022 (6)0.5345 (4)0.0274 (12)
H270.22542.06110.60030.033*
C280.2424 (5)2.0666 (5)0.4547 (4)0.0218 (10)
C290.3192 (6)2.2141 (6)0.4711 (4)0.0277 (12)
H290.34732.27700.53580.033*
C300.3530 (6)2.2658 (6)0.3917 (4)0.0290 (12)
H300.40742.36520.40030.035*
C310.3064 (6)2.1705 (6)0.2977 (4)0.0260 (11)
H310.32822.20870.24390.031*
C320.2051 (5)1.9802 (6)0.3578 (3)0.0215 (11)
C330.1271 (5)1.8279 (5)0.3387 (3)0.0210 (10)
C340.6437 (6)0.6252 (6)0.5886 (4)0.0276 (12)
H340.67780.57570.54040.033*
C350.6634 (6)0.5496 (6)0.6878 (4)0.0294 (12)
H350.70840.44810.70800.035*
C360.6179 (6)0.6217 (6)0.7562 (4)0.0268 (11)
H360.63370.56980.82420.032*
C370.5478 (5)0.7724 (5)0.7274 (4)0.0238 (11)
C380.4972 (6)0.8541 (6)0.7952 (4)0.0269 (11)
H380.50840.80620.86390.032*
C390.4333 (6)0.9990 (6)0.7635 (4)0.0275 (12)
H390.40311.05140.80980.033*
C400.4112 (5)1.0732 (6)0.6606 (4)0.0235 (11)
C410.3423 (6)1.2238 (6)0.6245 (4)0.0298 (12)
H410.31141.27960.66880.036*
C420.3207 (6)1.2879 (6)0.5268 (4)0.0322 (13)
H420.27751.38930.50140.039*
C430.3627 (5)1.2033 (6)0.4629 (4)0.0280 (12)
H430.34211.25020.39470.034*
C440.4522 (5)0.9982 (6)0.5910 (4)0.0198 (11)
C450.5276 (5)0.8437 (6)0.6255 (3)0.0231 (11)
C460.2254 (6)0.7322 (6)0.8653 (4)0.0370 (14)
H460.26900.63070.88820.044*
C470.1944 (7)0.8066 (7)0.9344 (4)0.0343 (15)
H470.21780.75641.00190.041*
C480.1301 (6)0.9523 (6)0.9030 (4)0.0316 (13)
H480.10781.00470.94880.038*
C490.0967 (5)1.0254 (6)0.8022 (4)0.0255 (11)
C500.0286 (5)1.1781 (6)0.7624 (4)0.0255 (11)
H500.00191.23620.80480.031*
C510.0026 (5)1.2391 (6)0.6651 (4)0.0260 (11)
H510.04291.34050.64020.031*
C520.0411 (5)1.1570 (6)0.5982 (4)0.0253 (11)
C530.0167 (6)1.2180 (6)0.4955 (4)0.0287 (12)
H530.02671.31890.46750.034*
C540.0557 (6)1.1312 (6)0.4368 (4)0.0270 (12)
H540.03471.17150.36840.032*
C550.1259 (6)0.9844 (6)0.4771 (4)0.0262 (11)
H550.15710.92460.43560.031*
C560.1094 (5)1.0079 (5)0.6353 (3)0.0205 (10)
C570.1364 (5)0.9385 (5)0.7395 (3)0.0235 (11)
C580.6083 (6)1.0556 (6)0.2559 (4)0.0354 (13)
H58A0.56111.09640.30990.053*
H58B0.57081.12810.19280.053*
H58C0.71221.02450.25840.053*
C590.3837 (6)0.9890 (8)0.2812 (5)0.0442 (16)
H59A0.34560.91760.29520.066*
H59B0.34161.06440.22000.066*
H59C0.35911.03080.33570.066*
O10.0544 (4)1.2653 (4)0.0241 (2)0.0232 (7)
O20.2516 (4)1.2526 (4)0.1156 (3)0.0313 (9)
O30.0386 (4)1.4951 (5)0.3015 (3)0.0365 (10)
O40.0820 (4)1.4254 (3)0.2307 (2)0.0224 (7)
O50.2825 (4)1.2997 (4)0.2228 (2)0.0237 (8)
O60.4872 (4)1.3728 (4)0.3087 (2)0.0279 (8)
O70.2408 (4)1.7992 (3)0.0822 (2)0.0246 (8)
O80.1265 (4)1.5639 (4)0.0103 (2)0.0236 (7)
O90.0411 (3)1.1243 (3)0.2129 (2)0.0203 (7)
O100.1179 (4)0.8896 (4)0.2879 (2)0.0265 (8)
O110.3584 (4)1.3055 (4)0.1099 (2)0.0259 (8)
O120.2730 (4)1.3829 (3)0.0188 (2)0.0237 (7)
O130.6314 (4)0.8034 (4)0.3684 (3)0.0361 (9)
O141.1684 (4)0.6103 (4)0.3790 (3)0.0316 (9)
H14A1.12410.71120.35090.038*
H14B1.11320.58110.35180.038*
O150.3899 (4)1.4263 (4)0.2256 (3)0.0348 (9)
H15A0.44731.41390.17480.042*
H15B0.35751.35890.18230.042*
O160.3079 (5)0.6530 (4)0.6028 (3)0.0427 (11)
H16A0.35580.63040.54500.051*
H16B0.34910.56710.65520.051*
O170.4315 (4)1.5831 (4)0.4392 (3)0.0385 (10)
H17A0.34411.59200.41920.046*
H17B0.51231.54080.40100.046*
O180.7177 (4)0.5189 (4)0.3788 (3)0.0319 (9)
H18A0.67730.61810.37230.038*
H18B0.78300.48540.32940.038*
N10.1196 (4)1.3584 (4)0.0993 (3)0.0173 (8)
N20.3370 (4)1.5585 (4)0.1120 (3)0.0195 (8)
N30.1199 (4)1.1258 (4)0.0899 (3)0.0173 (8)
N40.0982 (4)1.7415 (4)0.2452 (3)0.0210 (9)
H4A0.11841.78200.19270.025*
N50.2338 (4)2.0302 (4)0.2794 (3)0.0230 (9)
N60.5770 (4)0.7673 (4)0.5610 (3)0.0223 (9)
H6A0.57110.81770.49270.027*
N70.4295 (4)1.0614 (4)0.4924 (3)0.0240 (9)
N80.1977 (5)0.7944 (5)0.7706 (3)0.0279 (10)
N90.1502 (4)0.9265 (5)0.5734 (3)0.0235 (9)
H90.21040.82720.59730.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Y10.0206 (2)0.0181 (2)0.0154 (2)0.0093 (2)0.00083 (17)0.00465 (17)
S10.0338 (8)0.0343 (8)0.0200 (7)0.0186 (7)0.0039 (6)0.0110 (6)
C10.015 (3)0.017 (3)0.028 (3)0.005 (2)0.003 (2)0.007 (2)
C20.021 (3)0.017 (2)0.018 (2)0.007 (2)0.0003 (19)0.003 (2)
C30.020 (2)0.031 (3)0.018 (2)0.012 (2)0.0012 (19)0.005 (2)
C40.028 (3)0.039 (3)0.023 (3)0.020 (3)0.005 (2)0.005 (3)
C50.034 (3)0.034 (3)0.020 (2)0.021 (3)0.005 (2)0.007 (2)
C60.023 (2)0.018 (2)0.018 (2)0.009 (2)0.0027 (19)0.005 (2)
C70.030 (3)0.023 (3)0.017 (2)0.016 (3)0.000 (2)0.008 (2)
C80.036 (3)0.021 (3)0.009 (2)0.013 (3)0.005 (2)0.004 (2)
C90.023 (3)0.028 (3)0.013 (2)0.014 (2)0.0002 (19)0.008 (2)
C100.026 (3)0.032 (3)0.018 (2)0.010 (2)0.002 (2)0.009 (2)
C110.022 (3)0.029 (3)0.021 (3)0.004 (2)0.001 (2)0.012 (2)
C120.032 (3)0.021 (3)0.019 (2)0.005 (2)0.008 (2)0.006 (2)
C130.031 (3)0.022 (3)0.012 (2)0.011 (2)0.0037 (19)0.0079 (19)
C140.024 (3)0.019 (3)0.014 (2)0.013 (2)0.0023 (19)0.005 (2)
C150.018 (3)0.022 (3)0.019 (2)0.010 (2)0.000 (2)0.006 (2)
C160.023 (2)0.023 (3)0.016 (2)0.014 (2)0.0001 (19)0.003 (2)
C170.031 (3)0.018 (3)0.024 (3)0.010 (2)0.008 (2)0.003 (2)
C180.040 (3)0.023 (3)0.035 (3)0.012 (3)0.010 (3)0.010 (2)
C190.033 (3)0.026 (3)0.020 (2)0.016 (2)0.007 (2)0.008 (2)
C200.017 (2)0.019 (2)0.019 (2)0.007 (2)0.0017 (19)0.007 (2)
C210.017 (2)0.027 (3)0.019 (2)0.011 (2)0.0014 (19)0.007 (2)
C220.027 (3)0.025 (3)0.026 (3)0.011 (2)0.001 (2)0.003 (2)
C230.033 (3)0.026 (3)0.032 (3)0.012 (3)0.003 (2)0.012 (2)
C240.029 (3)0.032 (3)0.025 (3)0.015 (3)0.006 (2)0.014 (2)
C250.022 (3)0.029 (3)0.026 (3)0.015 (2)0.006 (2)0.011 (2)
C260.027 (3)0.036 (3)0.022 (3)0.018 (3)0.006 (2)0.016 (2)
C270.029 (3)0.037 (3)0.015 (2)0.016 (3)0.001 (2)0.005 (2)
C280.023 (3)0.025 (3)0.019 (2)0.013 (2)0.003 (2)0.004 (2)
C290.026 (3)0.032 (3)0.023 (3)0.013 (3)0.004 (2)0.003 (2)
C300.031 (3)0.018 (3)0.036 (3)0.009 (2)0.005 (2)0.005 (2)
C310.030 (3)0.026 (3)0.024 (3)0.010 (2)0.002 (2)0.013 (2)
C320.020 (3)0.027 (3)0.019 (2)0.011 (2)0.001 (2)0.007 (2)
C330.024 (3)0.027 (3)0.019 (2)0.016 (2)0.002 (2)0.007 (2)
C340.030 (3)0.021 (3)0.028 (3)0.006 (2)0.000 (2)0.010 (2)
C350.033 (3)0.022 (3)0.024 (3)0.010 (2)0.001 (2)0.000 (2)
C360.027 (3)0.028 (3)0.019 (3)0.010 (2)0.004 (2)0.002 (2)
C370.021 (3)0.025 (3)0.024 (3)0.009 (2)0.000 (2)0.007 (2)
C380.031 (3)0.031 (3)0.013 (2)0.011 (3)0.002 (2)0.003 (2)
C390.030 (3)0.038 (3)0.022 (3)0.017 (3)0.001 (2)0.013 (2)
C400.020 (3)0.030 (3)0.025 (3)0.012 (2)0.001 (2)0.011 (2)
C410.028 (3)0.026 (3)0.038 (3)0.011 (2)0.004 (2)0.014 (3)
C420.026 (3)0.020 (3)0.047 (3)0.008 (2)0.004 (3)0.006 (3)
C430.024 (3)0.026 (3)0.029 (3)0.011 (2)0.003 (2)0.001 (2)
C440.018 (2)0.025 (3)0.017 (2)0.010 (2)0.0005 (19)0.005 (2)
C450.022 (3)0.030 (3)0.020 (2)0.014 (2)0.000 (2)0.006 (2)
C460.046 (4)0.028 (3)0.025 (3)0.009 (3)0.006 (3)0.000 (2)
C470.037 (4)0.042 (4)0.014 (3)0.012 (3)0.002 (2)0.002 (3)
C480.031 (3)0.047 (4)0.021 (3)0.017 (3)0.002 (2)0.016 (3)
C490.024 (3)0.037 (3)0.024 (3)0.016 (3)0.003 (2)0.016 (2)
C500.023 (3)0.027 (3)0.029 (3)0.007 (2)0.000 (2)0.017 (2)
C510.026 (3)0.021 (3)0.030 (3)0.008 (2)0.002 (2)0.011 (2)
C520.025 (3)0.030 (3)0.025 (3)0.014 (2)0.002 (2)0.009 (2)
C530.032 (3)0.026 (3)0.026 (3)0.014 (3)0.008 (2)0.000 (2)
C540.031 (3)0.033 (3)0.019 (2)0.018 (3)0.004 (2)0.003 (2)
C550.030 (3)0.034 (3)0.019 (3)0.017 (3)0.004 (2)0.011 (2)
C560.019 (2)0.027 (3)0.019 (2)0.011 (2)0.001 (2)0.009 (2)
C570.025 (3)0.029 (3)0.019 (2)0.013 (2)0.003 (2)0.009 (2)
C580.044 (3)0.032 (3)0.035 (3)0.023 (3)0.005 (3)0.009 (3)
C590.041 (4)0.070 (5)0.042 (4)0.034 (4)0.006 (3)0.028 (3)
O10.0274 (19)0.0265 (19)0.0204 (17)0.0142 (16)0.0033 (14)0.0104 (15)
O20.031 (2)0.043 (2)0.028 (2)0.018 (2)0.0092 (17)0.0211 (19)
O30.041 (2)0.058 (3)0.034 (2)0.030 (2)0.0090 (18)0.033 (2)
O40.0299 (19)0.0225 (18)0.0167 (16)0.0108 (16)0.0029 (14)0.0076 (14)
O50.028 (2)0.0233 (19)0.0205 (17)0.0120 (17)0.0043 (15)0.0079 (15)
O60.029 (2)0.036 (2)0.0180 (18)0.0179 (19)0.0040 (15)0.0045 (16)
O70.035 (2)0.0182 (18)0.0184 (17)0.0110 (17)0.0005 (15)0.0025 (14)
O80.0233 (19)0.0223 (19)0.0205 (17)0.0085 (17)0.0006 (14)0.0028 (14)
O90.0236 (18)0.0159 (17)0.0204 (17)0.0075 (15)0.0049 (14)0.0032 (14)
O100.031 (2)0.0187 (19)0.0239 (19)0.0076 (17)0.0105 (16)0.0004 (15)
O110.027 (2)0.031 (2)0.0206 (18)0.0103 (18)0.0087 (15)0.0080 (16)
O120.0256 (19)0.0220 (18)0.0216 (17)0.0085 (16)0.0068 (14)0.0036 (14)
O130.052 (3)0.026 (2)0.0247 (19)0.0127 (19)0.0007 (18)0.0055 (16)
O140.040 (2)0.0213 (19)0.035 (2)0.0134 (18)0.0141 (17)0.0036 (16)
O150.035 (2)0.038 (2)0.0256 (19)0.0154 (19)0.0090 (17)0.0014 (17)
O160.058 (3)0.028 (2)0.025 (2)0.003 (2)0.0015 (19)0.0096 (18)
O170.035 (2)0.054 (3)0.031 (2)0.018 (2)0.0026 (17)0.021 (2)
O180.034 (2)0.025 (2)0.030 (2)0.0073 (18)0.0042 (17)0.0099 (17)
N10.0173 (19)0.017 (2)0.0138 (18)0.0063 (17)0.0002 (15)0.0022 (15)
N20.024 (2)0.020 (2)0.0183 (19)0.0097 (18)0.0009 (16)0.0095 (16)
N30.0168 (19)0.018 (2)0.0181 (19)0.0070 (17)0.0006 (15)0.0076 (16)
N40.020 (2)0.021 (2)0.021 (2)0.0089 (19)0.0018 (17)0.0063 (18)
N50.028 (2)0.024 (2)0.019 (2)0.011 (2)0.0001 (18)0.0082 (18)
N60.023 (2)0.023 (2)0.017 (2)0.0074 (19)0.0015 (17)0.0042 (18)
N70.024 (2)0.024 (2)0.019 (2)0.009 (2)0.0005 (17)0.0032 (18)
N80.036 (3)0.026 (2)0.021 (2)0.013 (2)0.0019 (19)0.0062 (19)
N90.025 (2)0.027 (2)0.019 (2)0.013 (2)0.0031 (17)0.0066 (18)
Geometric parameters (Å, º) top
Y1—O52.362 (3)C30—C311.401 (7)
Y1—O92.374 (3)C30—H300.9500
Y1—O82.386 (3)C31—N51.325 (6)
Y1—O122.398 (3)C31—H310.9500
Y1—O12.415 (3)C32—N51.350 (6)
Y1—O42.421 (3)C32—C331.438 (7)
Y1—N32.481 (4)C33—N41.348 (6)
Y1—N22.490 (4)C34—N61.331 (6)
Y1—N12.500 (4)C34—C351.384 (7)
S1—O131.513 (4)C34—H340.9500
S1—C591.774 (6)C35—C361.362 (7)
S1—C581.786 (5)C35—H350.9500
C1—O21.244 (6)C36—C371.410 (7)
C1—O11.263 (6)C36—H360.9500
C1—C21.520 (7)C37—C451.411 (7)
C2—N11.339 (6)C37—C381.425 (7)
C2—C31.384 (6)C38—C391.355 (7)
C3—C41.394 (7)C38—H380.9500
C3—H30.9500C39—C401.428 (7)
C4—C51.369 (7)C39—H390.9500
C4—H40.9500C40—C441.401 (7)
C5—C61.392 (7)C40—C411.411 (7)
C5—H50.9500C41—C421.349 (8)
C6—N11.333 (6)C41—H410.9500
C6—C71.516 (7)C42—C431.407 (8)
C7—O31.240 (6)C42—H420.9500
C7—O41.269 (6)C43—N71.328 (6)
C8—O61.233 (6)C43—H430.9500
C8—O51.261 (6)C44—N71.360 (6)
C8—C91.530 (7)C44—C451.449 (7)
C9—N21.332 (6)C45—N61.345 (6)
C9—C101.394 (7)C46—N81.316 (6)
C10—C111.390 (7)C46—C471.400 (8)
C10—H100.9500C46—H460.9500
C11—C121.387 (7)C47—C481.363 (8)
C11—H110.9500C47—H470.9500
C12—C131.381 (7)C48—C491.414 (7)
C12—H120.9500C48—H480.9500
C13—N21.348 (6)C49—C571.411 (7)
C13—C141.511 (7)C49—C501.434 (7)
C14—O71.243 (5)C50—C511.346 (7)
C14—O81.260 (6)C50—H500.9500
C15—O101.247 (6)C51—C521.425 (7)
C15—O91.255 (6)C51—H510.9500
C15—C161.522 (6)C52—C561.399 (7)
C16—N31.341 (6)C52—C531.414 (7)
C16—C171.387 (6)C53—C541.366 (7)
C17—C181.403 (7)C53—H530.9500
C17—H170.9500C54—C551.383 (7)
C18—C191.379 (7)C54—H540.9500
C18—H180.9500C55—N91.328 (6)
C19—C201.395 (6)C55—H550.9500
C19—H190.9500C56—N91.356 (6)
C20—N31.336 (6)C56—C571.445 (7)
C20—C211.516 (7)C57—N81.348 (6)
C21—O111.242 (6)C58—H58A0.9800
C21—O121.264 (6)C58—H58B0.9800
C22—N41.335 (6)C58—H58C0.9800
C22—C231.371 (7)C59—H59A0.9800
C22—H220.9500C59—H59B0.9800
C23—C241.364 (7)C59—H59C0.9800
C23—H230.9500O14—H14A0.9499
C24—C251.410 (7)O14—H14B0.9500
C24—H240.9500O15—H15A0.9501
C25—C331.417 (7)O15—H15B0.9501
C25—C261.432 (7)O16—H16A0.9499
C26—C271.357 (8)O16—H16B0.9501
C26—H260.9500O17—H17A0.9500
C27—C281.453 (7)O17—H17B0.9499
C27—H270.9500O18—H18A0.9499
C28—C321.396 (7)O18—H18B0.9502
C28—C291.398 (7)N4—H4A0.9499
C29—C301.370 (7)N6—H6A0.9501
C29—H290.9500N9—H90.9500
O5—Y1—O980.12 (11)C29—C30—H30120.3
O5—Y1—O8129.11 (11)C31—C30—H30120.3
O9—Y1—O8143.86 (11)N5—C31—C30123.9 (5)
O5—Y1—O1287.24 (11)N5—C31—H31118.1
O9—Y1—O12129.23 (11)C30—C31—H31118.1
O8—Y1—O1278.83 (11)N5—C32—C28124.3 (5)
O5—Y1—O1146.72 (11)N5—C32—C33116.6 (4)
O9—Y1—O185.57 (11)C28—C32—C33119.1 (5)
O8—Y1—O177.80 (11)N4—C33—C25119.3 (5)
O12—Y1—O178.82 (11)N4—C33—C32120.2 (4)
O5—Y1—O477.91 (11)C25—C33—C32120.5 (5)
O9—Y1—O478.84 (11)N6—C34—C35119.8 (5)
O8—Y1—O486.76 (11)N6—C34—H34120.1
O12—Y1—O4145.62 (11)C35—C34—H34120.1
O1—Y1—O4128.50 (11)C36—C35—C34119.7 (5)
O5—Y1—N374.91 (12)C36—C35—H35120.2
O9—Y1—N364.97 (11)C34—C35—H35120.2
O8—Y1—N3135.60 (12)C35—C36—C37120.8 (5)
O12—Y1—N364.26 (12)C35—C36—H36119.6
O1—Y1—N371.81 (11)C37—C36—H36119.6
O4—Y1—N3137.61 (12)C36—C37—C45117.1 (5)
O5—Y1—N264.65 (12)C36—C37—C38123.6 (5)
O9—Y1—N2137.89 (12)C45—C37—C38119.3 (5)
O8—Y1—N264.46 (12)C39—C38—C37121.3 (4)
O12—Y1—N273.53 (12)C39—C38—H38119.4
O1—Y1—N2136.49 (12)C37—C38—H38119.4
O4—Y1—N272.09 (12)C38—C39—C40120.3 (5)
N3—Y1—N2121.88 (12)C38—C39—H39119.8
O5—Y1—N1137.25 (12)C40—C39—H39119.8
O9—Y1—N174.06 (11)C44—C40—C41116.9 (5)
O8—Y1—N169.83 (12)C44—C40—C39120.9 (5)
O12—Y1—N1135.39 (11)C41—C40—C39122.2 (5)
O1—Y1—N164.36 (11)C42—C41—C40119.6 (5)
O4—Y1—N164.18 (12)C42—C41—H41120.2
N3—Y1—N1121.09 (13)C40—C41—H41120.2
N2—Y1—N1116.97 (12)C41—C42—C43119.3 (5)
O13—S1—C59106.4 (3)C41—C42—H42120.3
O13—S1—C58105.0 (3)C43—C42—H42120.3
C59—S1—C5898.2 (3)N7—C43—C42123.7 (5)
O2—C1—O1126.5 (5)N7—C43—H43118.1
O2—C1—C2118.4 (4)C42—C43—H43118.1
O1—C1—C2115.1 (4)N7—C44—C40124.1 (5)
N1—C2—C3121.5 (4)N7—C44—C45117.7 (4)
N1—C2—C1114.7 (4)C40—C44—C45118.2 (4)
C3—C2—C1123.8 (4)N6—C45—C37119.6 (5)
C2—C3—C4118.5 (5)N6—C45—C44120.5 (4)
C2—C3—H3120.7C37—C45—C44119.9 (4)
C4—C3—H3120.7N8—C46—C47124.0 (5)
C5—C4—C3119.8 (5)N8—C46—H46118.0
C5—C4—H4120.1C47—C46—H46118.0
C3—C4—H4120.1C48—C47—C46118.8 (5)
C4—C5—C6118.3 (4)C48—C47—H47120.6
C4—C5—H5120.9C46—C47—H47120.6
C6—C5—H5120.9C47—C48—C49119.9 (5)
N1—C6—C5122.1 (4)C47—C48—H48120.1
N1—C6—C7114.6 (4)C49—C48—H48120.1
C5—C6—C7123.3 (4)C57—C49—C48115.9 (5)
O3—C7—O4125.5 (5)C57—C49—C50120.2 (5)
O3—C7—C6119.1 (4)C48—C49—C50123.9 (5)
O4—C7—C6115.4 (4)C51—C50—C49120.1 (5)
O6—C8—O5128.2 (5)C51—C50—H50120.0
O6—C8—C9117.1 (5)C49—C50—H50120.0
O5—C8—C9114.7 (4)C50—C51—C52122.3 (5)
N2—C9—C10121.4 (5)C50—C51—H51118.9
N2—C9—C8113.8 (4)C52—C51—H51118.9
C10—C9—C8124.7 (4)C56—C52—C53117.8 (5)
C11—C10—C9118.4 (5)C56—C52—C51118.6 (4)
C11—C10—H10120.8C53—C52—C51123.6 (5)
C9—C10—H10120.8C54—C53—C52119.7 (5)
C12—C11—C10119.5 (5)C54—C53—H53120.1
C12—C11—H11120.2C52—C53—H53120.1
C10—C11—H11120.2C53—C54—C55119.9 (5)
C13—C12—C11119.0 (5)C53—C54—H54120.0
C13—C12—H12120.5C55—C54—H54120.0
C11—C12—H12120.5N9—C55—C54120.5 (5)
N2—C13—C12121.2 (5)N9—C55—H55119.7
N2—C13—C14113.9 (4)C54—C55—H55119.7
C12—C13—C14124.9 (4)N9—C56—C52120.2 (4)
O7—C14—O8126.4 (4)N9—C56—C57119.2 (5)
O7—C14—C13118.1 (4)C52—C56—C57120.6 (4)
O8—C14—C13115.5 (4)N8—C57—C49124.3 (5)
O10—C15—O9126.7 (4)N8—C57—C56117.5 (4)
O10—C15—C16118.0 (4)C49—C57—C56118.2 (5)
O9—C15—C16115.3 (4)S1—C58—H58A109.5
N3—C16—C17121.6 (4)S1—C58—H58B109.5
N3—C16—C15114.1 (4)H58A—C58—H58B109.5
C17—C16—C15124.3 (4)S1—C58—H58C109.5
C16—C17—C18118.7 (4)H58A—C58—H58C109.5
C16—C17—H17120.7H58B—C58—H58C109.5
C18—C17—H17120.7S1—C59—H59A109.5
C19—C18—C17119.2 (5)S1—C59—H59B109.5
C19—C18—H18120.4H59A—C59—H59B109.5
C17—C18—H18120.4S1—C59—H59C109.5
C18—C19—C20118.8 (4)H59A—C59—H59C109.5
C18—C19—H19120.6H59B—C59—H59C109.5
C20—C19—H19120.6C1—O1—Y1125.6 (3)
N3—C20—C19121.8 (4)C7—O4—Y1125.4 (3)
N3—C20—C21113.9 (4)C8—O5—Y1126.9 (3)
C19—C20—C21124.3 (4)C14—O8—Y1126.2 (3)
O11—C21—O12126.5 (5)C15—O9—Y1125.9 (3)
O11—C21—C20118.3 (4)C21—O12—Y1125.8 (3)
O12—C21—C20115.1 (4)H14A—O14—H14B102.1
N4—C22—C23119.9 (5)H15A—O15—H15B90.8
N4—C22—H22120.0H16A—O16—H16B105.2
C23—C22—H22120.0H17A—O17—H17B113.6
C24—C23—C22120.4 (5)H18A—O18—H18B118.2
C24—C23—H23119.8C6—N1—C2119.7 (4)
C22—C23—H23119.8C6—N1—Y1120.4 (3)
C23—C24—C25120.1 (5)C2—N1—Y1119.9 (3)
C23—C24—H24119.9C9—N2—C13120.4 (4)
C25—C24—H24119.9C9—N2—Y1119.8 (3)
C24—C25—C33117.4 (5)C13—N2—Y1119.8 (3)
C24—C25—C26123.7 (5)C20—N3—C16120.0 (4)
C33—C25—C26118.9 (5)C20—N3—Y1120.7 (3)
C27—C26—C25121.0 (5)C16—N3—Y1119.4 (3)
C27—C26—H26119.5C22—N4—C33122.6 (5)
C25—C26—H26119.5C22—N4—H4A116.8
C26—C27—C28120.7 (5)C33—N4—H4A119.6
C26—C27—H27119.7C31—N5—C32116.2 (4)
C28—C27—H27119.7C34—N6—C45123.1 (4)
C32—C28—C29117.8 (5)C34—N6—H6A118.6
C32—C28—C27119.8 (5)C45—N6—H6A118.1
C29—C28—C27122.4 (5)C43—N7—C44116.3 (4)
C30—C29—C28118.4 (5)C46—N8—C57117.1 (5)
C30—C29—H29120.8C55—N9—C56121.8 (5)
C28—C29—H29120.8C55—N9—H9118.2
C29—C30—C31119.3 (5)C56—N9—H9119.3
O2—C1—C2—N1172.6 (4)N3—Y1—O4—C7112.1 (4)
O1—C1—C2—N15.4 (6)N2—Y1—O4—C7129.9 (4)
O2—C1—C2—C35.0 (8)N1—Y1—O4—C73.4 (4)
O1—C1—C2—C3176.9 (5)O6—C8—O5—Y1176.2 (4)
N1—C2—C3—C42.0 (7)C9—C8—O5—Y14.1 (6)
C1—C2—C3—C4175.5 (5)O9—Y1—O5—C8153.6 (4)
C2—C3—C4—C51.2 (7)O8—Y1—O5—C82.6 (4)
C3—C4—C5—C60.5 (7)O12—Y1—O5—C875.8 (4)
C4—C5—C6—N11.4 (7)O1—Y1—O5—C8140.5 (4)
C4—C5—C6—C7179.4 (5)O4—Y1—O5—C873.0 (4)
N1—C6—C7—O3179.5 (5)N3—Y1—O5—C8139.9 (4)
C5—C6—C7—O30.2 (7)N2—Y1—O5—C82.7 (4)
N1—C6—C7—O40.6 (6)N1—Y1—O5—C8100.4 (4)
C5—C6—C7—O4179.8 (5)O7—C14—O8—Y1176.1 (3)
O6—C8—C9—N2177.3 (4)C13—C14—O8—Y12.6 (5)
O5—C8—C9—N23.0 (6)O5—Y1—O8—C141.9 (4)
O6—C8—C9—C104.1 (7)O9—Y1—O8—C14139.5 (3)
O5—C8—C9—C10175.6 (4)O12—Y1—O8—C1475.2 (4)
N2—C9—C10—C111.2 (7)O1—Y1—O8—C14156.0 (4)
C8—C9—C10—C11179.8 (4)O4—Y1—O8—C1473.4 (4)
C9—C10—C11—C120.9 (7)N3—Y1—O8—C14108.7 (4)
C10—C11—C12—C131.8 (7)N2—Y1—O8—C141.7 (3)
C11—C12—C13—N20.6 (7)N1—Y1—O8—C14137.1 (4)
C11—C12—C13—C14177.4 (4)O10—C15—O9—Y1172.5 (4)
N2—C13—C14—O7177.0 (4)C16—C15—O9—Y17.1 (6)
C12—C13—C14—O71.2 (7)O5—Y1—O9—C1572.6 (4)
N2—C13—C14—O81.9 (6)O8—Y1—O9—C15139.5 (3)
C12—C13—C14—O8179.9 (4)O12—Y1—O9—C155.6 (4)
O10—C15—C16—N3175.4 (4)O1—Y1—O9—C1577.3 (4)
O9—C15—C16—N34.2 (6)O4—Y1—O9—C15152.1 (4)
O10—C15—C16—C174.1 (7)N3—Y1—O9—C155.3 (4)
O9—C15—C16—C17176.3 (4)N2—Y1—O9—C15105.4 (4)
N3—C16—C17—C180.6 (7)N1—Y1—O9—C15141.8 (4)
C15—C16—C17—C18179.9 (5)O11—C21—O12—Y1173.9 (4)
C16—C17—C18—C191.2 (8)C20—C21—O12—Y17.1 (6)
C17—C18—C19—C202.8 (8)O5—Y1—O12—C2179.9 (4)
C18—C19—C20—N32.6 (8)O9—Y1—O12—C215.0 (4)
C18—C19—C20—C21178.5 (5)O8—Y1—O12—C21149.4 (4)
N3—C20—C21—O11176.7 (4)O1—Y1—O12—C2169.8 (4)
C19—C20—C21—O112.2 (7)O4—Y1—O12—C21143.6 (3)
N3—C20—C21—O124.2 (6)N3—Y1—O12—C215.3 (4)
C19—C20—C21—O12176.9 (5)N2—Y1—O12—C21144.2 (4)
N4—C22—C23—C240.2 (8)N1—Y1—O12—C21103.8 (4)
C22—C23—C24—C250.1 (8)C5—C6—N1—C20.6 (7)
C23—C24—C25—C332.5 (7)C7—C6—N1—C2179.9 (4)
C23—C24—C25—C26178.6 (5)C5—C6—N1—Y1176.9 (4)
C24—C25—C26—C27178.2 (5)C7—C6—N1—Y12.3 (5)
C33—C25—C26—C270.7 (7)C3—C2—N1—C61.2 (7)
C25—C26—C27—C280.7 (8)C1—C2—N1—C6176.6 (4)
C26—C27—C28—C320.4 (7)C3—C2—N1—Y1178.7 (3)
C26—C27—C28—C29178.7 (5)C1—C2—N1—Y11.0 (5)
C32—C28—C29—C300.3 (7)O5—Y1—N1—C632.8 (4)
C27—C28—C29—C30178.8 (5)O9—Y1—N1—C687.9 (3)
C28—C29—C30—C311.8 (7)O8—Y1—N1—C693.5 (3)
C29—C30—C31—N52.1 (8)O12—Y1—N1—C6141.7 (3)
C29—C28—C32—N52.4 (7)O1—Y1—N1—C6179.3 (4)
C27—C28—C32—N5176.7 (5)O4—Y1—N1—C62.8 (3)
C29—C28—C32—C33179.5 (4)N3—Y1—N1—C6134.6 (3)
C27—C28—C32—C331.4 (7)N2—Y1—N1—C648.1 (4)
C24—C25—C33—N45.1 (7)O5—Y1—N1—C2149.7 (3)
C26—C25—C33—N4175.9 (4)O9—Y1—N1—C294.5 (3)
C24—C25—C33—C32176.4 (4)O8—Y1—N1—C284.0 (3)
C26—C25—C33—C322.5 (7)O12—Y1—N1—C235.8 (4)
N5—C32—C33—N46.2 (7)O1—Y1—N1—C21.8 (3)
C28—C32—C33—N4175.6 (4)O4—Y1—N1—C2179.6 (4)
N5—C32—C33—C25175.4 (4)N3—Y1—N1—C247.9 (4)
C28—C32—C33—C252.9 (7)N2—Y1—N1—C2129.4 (3)
N6—C34—C35—C361.9 (8)C10—C9—N2—C132.5 (7)
C34—C35—C36—C371.6 (8)C8—C9—N2—C13178.8 (4)
C35—C36—C37—C450.1 (7)C10—C9—N2—Y1177.8 (3)
C35—C36—C37—C38179.8 (5)C8—C9—N2—Y10.8 (5)
C36—C37—C38—C39178.5 (5)C12—C13—N2—C91.6 (7)
C45—C37—C38—C391.6 (8)C14—C13—N2—C9179.8 (4)
C37—C38—C39—C402.0 (8)C12—C13—N2—Y1178.7 (3)
C38—C39—C40—C441.3 (7)C14—C13—N2—Y10.5 (5)
C38—C39—C40—C41178.6 (5)O5—Y1—N2—C90.7 (3)
C44—C40—C41—C420.7 (7)O9—Y1—N2—C935.5 (4)
C39—C40—C41—C42178.1 (5)O8—Y1—N2—C9179.2 (4)
C40—C41—C42—C432.2 (8)O12—Y1—N2—C995.5 (3)
C41—C42—C43—N73.2 (8)O1—Y1—N2—C9148.3 (3)
C41—C40—C44—N70.1 (7)O4—Y1—N2—C984.1 (3)
C39—C40—C44—N7177.3 (5)N3—Y1—N2—C951.3 (4)
C41—C40—C44—C45177.8 (4)N1—Y1—N2—C9131.5 (3)
C39—C40—C44—C454.8 (7)O5—Y1—N2—C13179.7 (4)
C36—C37—C45—N61.0 (7)O9—Y1—N2—C13144.2 (3)
C38—C37—C45—N6179.0 (4)O8—Y1—N2—C130.4 (3)
C36—C37—C45—C44178.0 (4)O12—Y1—N2—C1384.8 (3)
C38—C37—C45—C442.0 (7)O1—Y1—N2—C1332.0 (4)
N7—C44—C45—N62.1 (7)O4—Y1—N2—C1395.5 (3)
C40—C44—C45—N6175.9 (4)N3—Y1—N2—C13129.0 (3)
N7—C44—C45—C37176.9 (4)N1—Y1—N2—C1348.2 (4)
C40—C44—C45—C375.1 (7)C19—C20—N3—C160.8 (7)
N8—C46—C47—C480.9 (10)C21—C20—N3—C16179.7 (4)
C46—C47—C48—C490.3 (9)C19—C20—N3—Y1178.8 (3)
C47—C48—C49—C571.2 (7)C21—C20—N3—Y10.1 (5)
C47—C48—C49—C50179.7 (5)C17—C16—N3—C200.8 (7)
C57—C49—C50—C510.1 (7)C15—C16—N3—C20179.6 (4)
C48—C49—C50—C51179.0 (5)C17—C16—N3—Y1179.5 (3)
C49—C50—C51—C520.3 (8)C15—C16—N3—Y10.0 (5)
C50—C51—C52—C560.6 (8)O5—Y1—N3—C2096.6 (3)
C50—C51—C52—C53179.3 (5)O9—Y1—N3—C20177.4 (4)
C56—C52—C53—C542.0 (7)O8—Y1—N3—C2034.6 (4)
C51—C52—C53—C54179.4 (5)O12—Y1—N3—C202.3 (3)
C52—C53—C54—C553.5 (8)O1—Y1—N3—C2083.8 (3)
C53—C54—C55—N93.0 (8)O4—Y1—N3—C20148.5 (3)
C53—C52—C56—N90.1 (7)N2—Y1—N3—C2050.2 (4)
C51—C52—C56—N9178.6 (4)N1—Y1—N3—C20126.9 (3)
C53—C52—C56—C57179.4 (4)O5—Y1—N3—C1683.7 (3)
C51—C52—C56—C571.9 (7)O9—Y1—N3—C162.2 (3)
C48—C49—C57—N82.4 (7)O8—Y1—N3—C16145.1 (3)
C50—C49—C57—N8178.4 (4)O12—Y1—N3—C16178.0 (4)
C48—C49—C57—C56177.8 (4)O1—Y1—N3—C1695.9 (3)
C50—C49—C57—C561.3 (7)O4—Y1—N3—C1631.8 (4)
N9—C56—C57—N82.0 (7)N2—Y1—N3—C16130.1 (3)
C52—C56—C57—N8177.6 (4)N1—Y1—N3—C1652.8 (4)
N9—C56—C57—C49178.2 (4)C23—C22—N4—C332.5 (7)
C52—C56—C57—C492.2 (7)C25—C33—N4—C225.3 (7)
O2—C1—O1—Y1169.9 (4)C32—C33—N4—C22176.3 (4)
C2—C1—O1—Y17.9 (6)C30—C31—N5—C320.0 (7)
O5—Y1—O1—C1144.4 (4)C28—C32—N5—C312.2 (7)
O9—Y1—O1—C179.9 (4)C33—C32—N5—C31179.6 (4)
O8—Y1—O1—C167.8 (4)C35—C34—N6—C450.7 (8)
O12—Y1—O1—C1148.6 (4)C37—C45—N6—C340.7 (7)
O4—Y1—O1—C18.0 (4)C44—C45—N6—C34178.2 (5)
N3—Y1—O1—C1145.0 (4)C42—C43—N7—C442.3 (7)
N2—Y1—O1—C197.5 (4)C40—C44—N7—C430.7 (7)
N1—Y1—O1—C15.5 (4)C45—C44—N7—C43178.6 (4)
O3—C7—O4—Y1176.5 (4)C47—C46—N8—C570.3 (9)
C6—C7—O4—Y13.5 (6)C49—C57—N8—C462.0 (8)
O5—Y1—O4—C7163.1 (4)C56—C57—N8—C46178.3 (5)
O9—Y1—O4—C781.0 (4)C54—C55—N9—C560.9 (7)
O8—Y1—O4—C765.7 (4)C52—C56—N9—C550.7 (7)
O12—Y1—O4—C7130.5 (4)C57—C56—N9—C55178.9 (4)
O1—Y1—O4—C75.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14A···O10i0.951.842.734 (5)156
O14—H14B···O3ii0.951.822.757 (5)169
O15—H15A···O11i0.952.022.854 (5)146
O15—H15B···O20.951.892.824 (5)166
O16—H16A···O17iii0.951.732.678 (5)175
O16—H16B···O15iv0.951.842.769 (5)165
O17—H17A···O14v0.951.912.859 (5)180
O17—H17B···O18vi0.952.032.804 (5)138
O17—H17B···O6i0.952.603.192 (5)121
O18—H18A···O130.951.852.789 (5)169
O18—H18A···S10.952.773.650 (4)155
O18—H18B···O4ii0.951.902.849 (5)177
N4—H4A···O70.951.882.680 (5)140
N6—H6A···O130.951.842.673 (5)146
N9—H9···O160.951.692.612 (6)161
C3—H3···O11i0.952.493.319 (7)146
C5—H5···O6i0.952.593.277 (8)129
C22—H22···O80.952.333.056 (6)132
C29—H29···O6vii0.952.513.380 (7)152
C31—H31···O11vi0.952.413.357 (7)174
C34—H34···O180.952.533.446 (7)162
C36—H36···O12viii0.952.463.384 (6)164
C39—H39···O2ix0.952.543.438 (7)159
C42—H42···O14v0.952.363.247 (7)155
C54—H54···O90.952.443.275 (6)146
C55—H55···O100.952.403.244 (7)147
C59—H59A···O100.982.553.381 (9)143
C58—H58C···Cg1 (N3,C16-C20)i0.982.843.424 (7)119
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1, z; (iii) x, y1, z; (iv) x, y1, z+1; (v) x1, y+1, z; (vi) x, y+1, z; (vii) x, y+1, z1; (viii) x+1, y1, z+1; (ix) x, y, z+1.

Experimental details

Crystal data
Chemical formula(C12H9N2)3[Y(C7H3NO4)3]·C2H6OS·5H2O
Mr1296.08
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)10.4185 (14), 10.9689 (14), 14.3844 (19)
α, β, γ (°)70.599 (2), 81.174 (2), 63.298 (2)
V3)1385.1 (3)
Z1
Radiation typeMo Kα
µ (mm1)1.18
Crystal size (mm)0.30 × 0.20 × 0.17
Data collection
DiffractometerBruker SMART 1000
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.719, 0.825
No. of measured, independent and
observed [I > 2σ(I)] reflections
15984, 11832, 8989
Rint0.045
(sin θ/λ)max1)0.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.131, 1.00
No. of reflections11832
No. of parameters795
No. of restraints3
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.70, 0.85
Absolute structureFlack (1983), 5621 Friedel pairs
Absolute structure parameter0.004 (4)

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2005).

Selected geometric parameters (Å, º) top
Y1—O52.362 (3)Y1—O42.421 (3)
Y1—O92.374 (3)Y1—N32.481 (4)
Y1—O82.386 (3)Y1—N22.490 (4)
Y1—O122.398 (3)Y1—N12.500 (4)
Y1—O12.415 (3)
O5—Y1—O980.12 (11)O9—Y1—O478.84 (11)
O8—Y1—O1278.83 (11)N3—Y1—N2121.88 (12)
O8—Y1—O177.80 (11)N3—Y1—N1121.09 (13)
O12—Y1—O178.82 (11)N2—Y1—N1116.97 (12)
O5—Y1—O477.91 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O14—H14A···O10i0.951.842.734 (5)156.0
O14—H14B···O3ii0.951.822.757 (5)169.3
O15—H15A···O11i0.952.022.854 (5)146.2
O15—H15B···O20.951.892.824 (5)165.8
O16—H16A···O17iii0.951.732.678 (5)174.6
O16—H16B···O15iv0.951.842.769 (5)165.2
O17—H17A···O14v0.951.912.859 (5)179.9
O17—H17B···O18vi0.952.032.804 (5)137.6
O17—H17B···O6i0.952.603.192 (5)120.6
O18—H18A···O130.951.852.789 (5)169.3
O18—H18A···S10.952.773.650 (4)154.6
O18—H18B···O4ii0.951.902.849 (5)176.8
N4—H4A···O70.951.882.680 (5)139.7
N6—H6A···O130.951.842.673 (5)145.5
N9—H9···O160.951.692.612 (6)161.4
C3—H3···O11i0.952.493.319 (7)146
C5—H5···O6i0.952.593.277 (8)129
C22—H22···O80.952.333.056 (6)132
C29—H29···O6vii0.952.513.380 (7)152
C31—H31···O11vi0.952.413.357 (7)174
C34—H34···O180.952.533.446 (7)162
C36—H36···O12viii0.952.463.384 (6)164
C39—H39···O2ix0.952.543.438 (7)159
C42—H42···O14v0.952.363.247 (7)155
C54—H54···O90.952.443.275 (6)146
C55—H55···O100.952.403.244 (7)147
C59—H59A···O100.982.553.381 (9)143
C58—H58C···Cg1 (N3,C16-C20)i0.982.843.424 (7)119
Symmetry codes: (i) x+1, y, z; (ii) x+1, y1, z; (iii) x, y1, z; (iv) x, y1, z+1; (v) x1, y+1, z; (vi) x, y+1, z; (vii) x, y+1, z1; (viii) x+1, y1, z+1; (ix) x, y, z+1.
 

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