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In the title compound [systematic name: tri­aqua(1,4,7,10,13,16-hexaoxa­cyclo­octa­decane-κ6O)(2-nitro­phenolato-κO)­barium(II)–aqua(1,4,7,10,13,16-hexaoxa­cyclo­octa­decane-κ6O)- bis(2-nitro­phenolato-κ2O,O′)­barium(II)–2-nitro­phenolate (1/1/1)], [Ba(C12H24O6)(C6H4NO3)(H2O)3][Ba(C12H24O6)(C6H4NO3)2(H2O)](C6H4NO3), the two BaII atoms encapsulated by the 18-crown-6 rings have different coordinations. Although both BaII atoms are coordinated to the six O atoms of the crowns, in the neutral moiety, the BaII atom is coordinated to one terminal O atom from a water mol­ecule, two phenolate O atoms and two nitro-group O atoms, while in the cationic moiety, the BaII atom is coordinated to three terminal O atoms from water mol­ecules and one phenolate O atom. Both the crowns are eclipsed and translated along the b direction. In the asymmetric unit, the three components are interconnected by four O—H...O interactions. The packing is stabilized by two intermolecular C—H...O interactions and by one O—H...O interaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102016451/av1117sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102016451/av1117Isup2.hkl
Contains datablock I

CCDC reference: 199403

Comment top

Several complexes of barium with 1,4,7,10,13,16-hexaoxacyclooctadecane (18-crown-6) have been reported (Wei et al., 1988; Rheingold et al., 1993; Usman et al., 2002). In these papers, analyses of the structures of the complexes and the temperature-dependent crystal cell parameters were the main interest. As part of our systematic studies of the temperature-dependent crystal cell parameters of 18-crown-6 complexed with barium(II) phenolate derivatives, we have prepared the title ternary complex, (I). However, the cell parameters are almost constant in the temperature range from 300 K to 183 K. An X-ray crystal structure determination of (I) was undertaken at 300 K, and the result is reported here. Compound (I) is a ternary complex of neutral aqua-18-crown-6-barium(II)bis(o-nitrophenolate), a triaqua-18-crown-6-barium(II)-o-nitrophenolate cation, and an o-nitrophenolate anion. \sch

In the neutral moiety, the Ba2+ cation is eleven-coordinate, which is rare for Ba in 18-crown-6-barium(II) complexes, to the six O atoms of the crown (average Ba—Ocrown 2.970 Å), to the water O atom on one side [Ba—Owater 2.836 (4) Å] and to the O atoms of the phenolate and nitro groups of two o-nitrophenolates on the opposite side (average Ba—Ophenolate 2.700 Å and Ba—Onitro 2.989 Å). These average B—O bond lengths are slightly elongated when compared with those in related structures [Ba—Ocrown 2.823 Å (Rheingold et al.,1993) and 2.794 Å (Usman et al., 2002), and Ba—Ophenolate 2.689 Å and Ba—Onitro 2.995 Å (Usman et al., 2002)].

The rigid 18-crown-6, as is usually observed, has approximately D3 d symmetry, with average C—O and C—C bond distances of 1.434 and 1.479 Å, respectively, and O—C—C—O and C—O—C—C torsion angles close to +sc or -sc and ap. The O atoms of the crown form a regular hexagon ether, with nonbonded O···O distances in the range 2.771 (5)–2.871 (5) Å, and, together with atoms Ba1 and O7, they form a distorted hexagonal bipyramid. The apices Ba1 and O7 are displaced by 1.055 (1) and 1.775 (1) Å, respectively, from the basal hexagon O ether. The aromatic rings, A and B, of the two phenolates and the crown plane make dihedral angles of 12.8 (2) and 14.9 (2)°, respectively. The nitro groups (N1/O9/O10 and N2/O12/O13) are twisted by an angle of 7.1 (3)° from their attached aromatic ring.

In the cationic moiety, the Ba2+ cation is ten-coordinate, as is usually observed in 18-crown-6-barium(II) complexes (Wei et al., 1988; Rheingold et al., 1993; Usman et al., 2002), to the six O atoms of the crown (average Ba—Ocrown 2.856 Å), to the three water O molecules (average Ba—Owater 2.825 Å) and to the phenolate O atom [Ba—Ophenolate 2.982 (5) Å]. The average Ba—Ocrown and Ba—Owater bond lengths are slightly shorter, whereas the Ba—Ophenolate bond is slightly longer, when compared with the corresponding values in the neutral moiety.

The crown ether of this moiety also adopts approximately D3 d symmetry. The average C—O and C—C bond distances [1.430 and 1.484 Å, respectively], the O—C—C and C—O—C angles [average O—C—C 109.3° and C—O—C 112.2°], and O—C—C—O and C—O—C—C torsion angles are all comparable with those in the neutral moiety. Also similar is the hexagonal bipyramid formed by the regular hexagon of the O atoms of the crown ether, with atoms Ba2 and O20 being the apices. The O···O distances of the hexagon are in the range 2.778 (5)–2.826 (6) Å, and atoms Ba2 and O20 are displaced by 0.656 and 2.056 Å, respectively. The aromatic ring C of the phenolate and the crown plane make a dihedral angle of 19.9 (2)°, and the nitro group (N3/O22/O23) is twisted by an angle of 31.7 (3)° from the aromatic ring.

In the phenolate counteranion, D, the nitro group (N4/O27/O28) is twisted by an angle of 25.8 (3)° from the aromatic ring. This ring is coplanar with aromatic ring C, the corresponding angle between these two being 0.6 (2)°. The closest atom to Ba2 is atom O26, with Ba2···O26 4.277 (5) Å.

It should be noted that both crown ring systems (neutral and cation moieties) are eclipsed and coplanar to each other, with the average Ocrown—Ba1···Ba2—Ocrown torsion angle being 1.0° and the dihedral angle between the crown ring systems being 1.7 (1)°. The crown of the neutral moiety is translated by 6.766 Å from the crown of the cation moiety, approximately along the b direction. However, the two pairs of phenolates, A and B, and C and D, have slightly different orientations towards their crown rings due to the different Ba—Onitro bonds. The twisted angles of the nitro groups of phenolates A and B are also much smaller compared with those in phenolates C and D.

In the asymmetric unit of (I), the three components are interconnected via intermolecular O20—H12W···O11, O20—H12W···O12, O20—H22W···O8 and O25—H24W···O27 interactions (Table 2). The symmetry-related neutral and cationic moieties are linked by a C3—H3A···O26i intermolecular bond into molecular columns along the b direction, and these molecular columns are interconnected by C36—H36A···O27ii and O7—H21W···O26ii interactions (Fig. 2) [symmetry codes: (i) x, y - 1, z; (ii) 2 - x, 1 - y, 1 - z].

Experimental top

The title ternary complex was prepared by thoroughly mixing Ba(OH)2·8H2O (1.58 g, 5 mmol), 2-nitrophenol (1.39 g, 10 mmol) and 18-crown-6 (1.32 g, 5 mmol) in ethanol (50 ml). Distilled water (2 mmol Should this be 2 ml?) was then added and the mixture was warmed until a solution was obtained. The solution was filtered and left to evaporate slowly in air. Orange block single crystals of (I) suitable for X-ray data collection were obtained from the solution after a few days.

Refinement top

Rigid regular phenyl groups were fitted for all the phenolate aromatic rings. All H atoms were geometrically fixed with ideal bond lengths and angles, and were treated as riding atoms with Uiso(H) = 1.2Ueq(C, N). Owing to the crystal not being of the best quality, the completeness is less than 0.92. The residual highest peak and deepest hole are 2.47 e Å-3 (0.05 Å from Ba2) and 2.90 e Å-3 (0.94 Å from Ba1), respectively.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme and with 50% probability displacement ellipsoids. For the sake of clarity, all H atoms have been omitted.
[Figure 2] Fig. 2. The packing diagram for (I). Dashed lines denote the intermolecular C—H···O and O—H···O interactions. All H atoms have been omitted, except those involved in the intermolecular interactions.
triaqua(1,4,7,10,13,16-hexaoxacyclooctadecane-κ6O)(2-nitrophenolato- κO)barium(II)–2-nitrophenolate–aqua(1,4,7,10,13,16- hexaoxacyclooctadecane-κ6O)bis(2-nitrophenolato-κ2O,O')barium(II) (1/1/1) top
Crystal data top
[Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)]Z = 2
Mr = 1427.78F(000) = 1448
Triclinic, P1Dx = 1.597 Mg m3
a = 13.7492 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.9672 (3) ÅCell parameters from 7466 reflections
c = 16.8669 (3) Åθ = 2.5–28.3°
α = 97.9362 (2)°µ = 1.41 mm1
β = 109.7546 (7)°T = 293 K
γ = 108.8642 (7)°Block, orange
V = 2969.6 (1) Å30.24 × 0.22 × 0.20 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
13455 independent reflections
Radiation source: fine-focus sealed tube10337 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.081
Detector resolution: 8.33 pixels mm-1θmax = 28.3°, θmin = 2.5°
ω scansh = 1118
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1919
Tmin = 0.729, Tmax = 0.766l = 2215
17916 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)] = 0.063H-atom parameters constrained
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.0328P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.96(Δ/σ)max = 0.001
13455 reflectionsΔρmax = 2.47 e Å3
692 parametersΔρmin = 2.90 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0175 (7)
Crystal data top
[Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)]γ = 108.8642 (7)°
Mr = 1427.78V = 2969.6 (1) Å3
Triclinic, P1Z = 2
a = 13.7492 (3) ÅMo Kα radiation
b = 14.9672 (3) ŵ = 1.41 mm1
c = 16.8669 (3) ÅT = 293 K
α = 97.9362 (2)°0.24 × 0.22 × 0.20 mm
β = 109.7546 (7)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
13455 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
10337 reflections with I > 2σ(I)
Tmin = 0.729, Tmax = 0.766Rint = 0.081
17916 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.171H-atom parameters constrained
S = 0.96Δρmax = 2.47 e Å3
13455 reflectionsΔρmin = 2.90 e Å3
692 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 30 s covered 0.3° in ω. The crystal-to-detector distance was 5 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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
Ba10.00994 (2)0.022354 (19)0.250290 (16)0.02284 (11)
Ba20.03274 (2)0.414640 (19)0.243444 (17)0.02569 (11)
N10.2253 (4)0.2357 (4)0.4262 (3)0.0406 (11)
N20.2356 (5)0.0141 (4)0.0846 (3)0.0518 (14)
N30.3297 (5)0.4673 (4)0.0473 (3)0.0506 (14)
N40.3601 (4)0.7976 (4)0.4740 (3)0.0451 (12)
O10.0163 (3)0.0789 (3)0.4117 (2)0.0365 (8)
O20.2255 (3)0.0223 (3)0.4003 (2)0.0355 (8)
O30.1996 (3)0.0557 (3)0.2311 (2)0.0418 (9)
O40.0147 (4)0.0765 (3)0.0811 (2)0.0422 (9)
O50.1939 (3)0.1764 (3)0.0924 (2)0.0385 (9)
O60.1802 (3)0.1921 (3)0.2572 (2)0.0395 (9)
O70.0108 (3)0.2130 (3)0.2371 (3)0.0482 (10)
H1W10.04510.26470.19310.072*
H2W10.06730.22180.27700.072*
O80.1372 (3)0.1474 (3)0.2358 (3)0.0453 (10)
O90.1270 (4)0.1724 (3)0.3930 (3)0.0478 (10)
O100.2683 (4)0.2850 (4)0.5031 (3)0.0682 (14)
O110.1345 (3)0.0555 (3)0.2759 (3)0.0436 (9)
O120.1355 (4)0.0366 (3)0.1152 (3)0.0512 (10)
O130.2894 (6)0.0031 (6)0.0067 (4)0.106 (3)
O140.0341 (3)0.3823 (3)0.4055 (2)0.0375 (9)
O150.1715 (3)0.4434 (3)0.3871 (2)0.0364 (8)
O160.1746 (3)0.4587 (3)0.2256 (2)0.0364 (8)
O170.0278 (3)0.3499 (3)0.0772 (2)0.0353 (8)
O180.2357 (3)0.3064 (3)0.0921 (2)0.0358 (8)
O190.2324 (3)0.2854 (3)0.2528 (3)0.0424 (9)
O200.0166 (4)0.2386 (3)0.2406 (3)0.0504 (11)
H1W20.07880.18380.22520.076*
H2W20.05100.23490.25490.076*
O210.1538 (4)0.5488 (4)0.2217 (3)0.0658 (14)
O220.2441 (5)0.5154 (4)0.0416 (3)0.0694 (14)
O230.4053 (5)0.3967 (4)0.0149 (3)0.0827 (18)
O240.0079 (3)0.5676 (3)0.1566 (2)0.0409 (9)
H1W30.03140.60590.15220.061*
H2W30.05980.57700.13390.061*
O250.0383 (3)0.6025 (3)0.3634 (2)0.0389 (9)
H1W40.00340.63850.35190.058*
H2W40.10220.62520.41250.058*
O260.1824 (3)0.7160 (3)0.2995 (3)0.0423 (9)
O270.2708 (4)0.7563 (4)0.4771 (3)0.0726 (16)
O280.4388 (4)0.8640 (5)0.5382 (3)0.0865 (18)
C10.1213 (5)0.0735 (5)0.4741 (4)0.0432 (14)
H1A0.13540.13040.45480.052*
H1B0.11840.07260.53080.052*
C20.2131 (5)0.0184 (5)0.4809 (3)0.0447 (14)
H2A0.19800.07440.50090.054*
H2B0.28380.02410.52480.054*
C30.2910 (4)0.0295 (4)0.3835 (4)0.0395 (13)
H3A0.25220.09910.37520.047*
H3B0.36330.00580.43310.047*
C40.3080 (5)0.0130 (5)0.3029 (4)0.0428 (13)
H4A0.34290.05680.30970.051*
H4B0.35640.04380.29260.051*
C50.2035 (6)0.0586 (5)0.1473 (4)0.0538 (17)
H5A0.25730.08560.14260.065*
H5B0.22840.00760.14140.065*
C60.0948 (5)0.1177 (5)0.0783 (4)0.0492 (15)
H6A0.06960.18380.08450.059*
H6B0.09990.12150.02210.059*
C70.0956 (5)0.1236 (5)0.0055 (4)0.0470 (15)
H7A0.12970.07630.00370.056*
H7B0.08510.14500.04690.056*
C80.1698 (6)0.2075 (5)0.0200 (4)0.0518 (16)
H8A0.23940.24080.03220.062*
H8B0.13440.25350.03180.062*
C90.2757 (5)0.2570 (4)0.1039 (4)0.0463 (14)
H9A0.25170.31120.10610.056*
H9B0.34790.27970.05430.056*
C100.2879 (4)0.2249 (4)0.1865 (4)0.0394 (12)
H10A0.31410.17200.18410.047*
H10B0.34210.27930.19450.047*
C110.1827 (5)0.1704 (5)0.3411 (4)0.0428 (14)
H11A0.24510.22230.34340.051*
H11B0.19240.10920.35240.051*
C120.0727 (5)0.1618 (5)0.4091 (4)0.0409 (13)
H12A0.07570.15480.46620.049*
H12B0.05990.22080.39440.049*
C130.2445 (2)0.0316 (3)0.2310 (2)0.0355 (11)
C140.3076 (3)0.0297 (3)0.28049 (19)0.0488 (15)
H140.27220.04840.34140.059*
C150.4236 (3)0.0001 (4)0.2390 (3)0.071 (2)
H150.46580.00120.27210.085*
C160.4765 (2)0.0278 (4)0.1480 (3)0.078 (3)
H160.55410.04760.12020.094*
C170.4133 (3)0.0260 (3)0.0985 (2)0.0565 (17)
H170.44870.04460.03760.068*
C180.2973 (3)0.0037 (3)0.1400 (2)0.0384 (12)
C190.2466 (2)0.2082 (2)0.2851 (2)0.0353 (11)
C200.3160 (3)0.2276 (3)0.2404 (2)0.0481 (15)
H200.28710.19820.18050.058*
C210.4287 (3)0.2910 (4)0.2852 (3)0.065 (2)
H210.47520.30400.25530.078*
C220.4720 (2)0.3350 (4)0.3747 (3)0.078 (3)
H220.54740.37740.40470.094*
C230.4026 (3)0.3155 (3)0.4194 (2)0.0596 (18)
H230.43160.34500.47930.072*
C240.2899 (3)0.2521 (3)0.3746 (2)0.0355 (11)
C250.0650 (5)0.3876 (5)0.4694 (4)0.0475 (15)
H25A0.07220.32530.45780.057*
H25B0.06260.40050.52650.057*
C260.1658 (5)0.4690 (5)0.4696 (4)0.0470 (15)
H26A0.15730.53100.47810.056*
H26B0.23430.47590.51680.056*
C270.2698 (5)0.5131 (4)0.3826 (4)0.0434 (13)
H27A0.33720.52230.43230.052*
H27B0.26400.57610.38410.052*
C280.2764 (5)0.4740 (4)0.2997 (4)0.0407 (13)
H28A0.34120.52010.29510.049*
H28B0.28530.41230.29950.049*
C290.1711 (6)0.4117 (5)0.1450 (4)0.0503 (16)
H29A0.16500.34510.14400.060*
H29B0.24010.44700.13920.060*
C300.0742 (5)0.4096 (5)0.0716 (4)0.0409 (13)
H30A0.07790.47580.07410.049*
H30B0.07520.38240.01630.049*
C310.1273 (6)0.3452 (5)0.0085 (3)0.0448 (14)
H31A0.12550.32580.04810.054*
H31B0.13110.40920.01580.054*
C320.2258 (5)0.2733 (5)0.0128 (4)0.0473 (15)
H32A0.29310.26370.03700.057*
H32B0.21850.21070.01030.057*
C330.3306 (5)0.2357 (4)0.0983 (4)0.0474 (14)
H33A0.32410.17270.09340.057*
H33B0.39940.22740.05060.057*
C340.3351 (5)0.2696 (5)0.1840 (4)0.0466 (14)
H34A0.34720.33010.18730.056*
H34B0.39710.22040.18930.056*
C350.2347 (5)0.3011 (5)0.3367 (4)0.0460 (14)
H35A0.29990.24960.33600.055*
H35B0.23940.36380.35320.055*
C360.1304 (6)0.3003 (5)0.4001 (4)0.0487 (15)
H36A0.13270.30540.45740.058*
H36B0.12390.23900.38150.058*
C370.2601 (2)0.5343 (3)0.2081 (2)0.0407 (13)
C380.2836 (3)0.5573 (3)0.2804 (2)0.0502 (15)
H380.22550.58530.33610.060*
C390.3939 (4)0.5386 (4)0.2693 (3)0.066 (2)
H390.40960.55400.31770.079*
C400.4807 (3)0.4968 (4)0.1860 (3)0.079 (3)
H400.55450.48420.17860.095*
C410.4572 (3)0.4737 (3)0.1137 (2)0.0585 (18)
H410.51530.44570.05790.070*
C420.3469 (3)0.4925 (3)0.1247 (2)0.0398 (13)
C430.2894 (2)0.7333 (3)0.3130 (2)0.0340 (11)
C440.3127 (3)0.7111 (3)0.24047 (18)0.0506 (15)
H440.25450.68360.18470.061*
C450.4229 (4)0.7300 (4)0.2512 (3)0.076 (2)
H450.43850.71520.20270.091*
C460.5099 (3)0.7712 (4)0.3345 (3)0.074 (2)
H460.58360.78380.34170.089*
C470.4866 (2)0.7934 (4)0.4071 (2)0.0545 (17)
H470.54470.82090.46280.065*
C480.3763 (3)0.7744 (3)0.39634 (19)0.0365 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ba10.02353 (17)0.02290 (16)0.02523 (16)0.01037 (12)0.01214 (12)0.00759 (11)
Ba20.03054 (19)0.02262 (16)0.02452 (16)0.00905 (13)0.01297 (12)0.00757 (11)
N10.044 (3)0.042 (3)0.039 (2)0.018 (2)0.017 (2)0.018 (2)
N20.074 (4)0.058 (4)0.039 (3)0.042 (3)0.022 (3)0.023 (2)
N30.055 (4)0.047 (3)0.046 (3)0.030 (3)0.008 (3)0.011 (2)
N40.044 (3)0.044 (3)0.046 (3)0.016 (2)0.018 (2)0.014 (2)
O10.034 (2)0.046 (2)0.0339 (19)0.0151 (18)0.0165 (16)0.0204 (17)
O20.038 (2)0.040 (2)0.0349 (19)0.0186 (18)0.0167 (16)0.0155 (16)
O30.032 (2)0.054 (3)0.043 (2)0.0161 (19)0.0209 (17)0.0119 (18)
O40.053 (3)0.046 (2)0.0326 (19)0.022 (2)0.0221 (18)0.0062 (17)
O50.047 (2)0.029 (2)0.0335 (19)0.0088 (18)0.0172 (17)0.0057 (15)
O60.0276 (19)0.042 (2)0.042 (2)0.0031 (17)0.0187 (16)0.0074 (17)
O70.041 (2)0.034 (2)0.075 (3)0.0168 (19)0.026 (2)0.019 (2)
O80.046 (2)0.033 (2)0.045 (2)0.0028 (18)0.0185 (19)0.0074 (17)
O90.044 (2)0.053 (3)0.056 (3)0.016 (2)0.031 (2)0.023 (2)
O100.074 (4)0.084 (4)0.038 (2)0.022 (3)0.024 (2)0.009 (2)
O110.032 (2)0.054 (3)0.048 (2)0.022 (2)0.0151 (18)0.0152 (19)
O120.053 (3)0.049 (3)0.054 (3)0.019 (2)0.026 (2)0.015 (2)
O130.103 (5)0.202 (8)0.051 (3)0.097 (6)0.034 (3)0.058 (4)
O140.045 (2)0.041 (2)0.0332 (19)0.0167 (19)0.0217 (17)0.0183 (16)
O150.041 (2)0.037 (2)0.0291 (18)0.0118 (18)0.0162 (16)0.0090 (15)
O160.038 (2)0.041 (2)0.0367 (19)0.0189 (18)0.0194 (17)0.0119 (16)
O170.048 (2)0.035 (2)0.0286 (17)0.0206 (18)0.0171 (16)0.0111 (15)
O180.036 (2)0.029 (2)0.0340 (19)0.0080 (17)0.0113 (16)0.0069 (15)
O190.032 (2)0.054 (3)0.044 (2)0.0121 (19)0.0208 (18)0.0191 (19)
O200.055 (3)0.024 (2)0.077 (3)0.0161 (19)0.031 (2)0.0160 (19)
O210.032 (2)0.100 (4)0.054 (3)0.027 (3)0.011 (2)0.002 (3)
O220.077 (4)0.074 (4)0.070 (3)0.033 (3)0.042 (3)0.018 (3)
O230.073 (4)0.068 (4)0.065 (3)0.033 (3)0.014 (3)0.012 (3)
O240.046 (2)0.037 (2)0.047 (2)0.0191 (19)0.0255 (19)0.0088 (17)
O250.034 (2)0.041 (2)0.0360 (19)0.0105 (17)0.0110 (16)0.0121 (16)
O260.0226 (19)0.042 (2)0.052 (2)0.0057 (17)0.0086 (17)0.0147 (18)
O270.042 (3)0.091 (4)0.053 (3)0.011 (3)0.025 (2)0.001 (3)
O280.058 (3)0.097 (5)0.054 (3)0.001 (3)0.009 (3)0.013 (3)
C10.033 (3)0.051 (4)0.038 (3)0.010 (3)0.008 (2)0.022 (3)
C20.043 (3)0.052 (4)0.028 (3)0.011 (3)0.008 (2)0.013 (2)
C30.024 (3)0.038 (3)0.050 (3)0.013 (2)0.006 (2)0.011 (2)
C40.026 (3)0.046 (3)0.059 (4)0.014 (3)0.021 (3)0.013 (3)
C50.054 (4)0.065 (4)0.057 (4)0.022 (3)0.042 (3)0.013 (3)
C60.050 (4)0.058 (4)0.046 (3)0.023 (3)0.029 (3)0.003 (3)
C70.052 (4)0.059 (4)0.028 (3)0.019 (3)0.019 (3)0.009 (3)
C80.058 (4)0.046 (4)0.033 (3)0.010 (3)0.014 (3)0.006 (3)
C90.049 (4)0.026 (3)0.046 (3)0.002 (3)0.013 (3)0.002 (2)
C100.031 (3)0.032 (3)0.051 (3)0.006 (2)0.017 (2)0.013 (2)
C110.036 (3)0.050 (4)0.047 (3)0.009 (3)0.031 (3)0.016 (3)
C120.042 (3)0.051 (4)0.044 (3)0.017 (3)0.029 (3)0.029 (3)
C130.034 (3)0.028 (3)0.049 (3)0.013 (2)0.020 (2)0.017 (2)
C140.053 (4)0.057 (4)0.045 (3)0.022 (3)0.026 (3)0.024 (3)
C150.039 (4)0.090 (6)0.091 (6)0.018 (4)0.037 (4)0.035 (5)
C160.016 (3)0.082 (6)0.107 (7)0.004 (3)0.004 (4)0.034 (5)
C170.046 (4)0.053 (4)0.051 (4)0.012 (3)0.003 (3)0.021 (3)
C180.040 (3)0.034 (3)0.046 (3)0.017 (3)0.018 (3)0.018 (2)
C190.035 (3)0.027 (3)0.048 (3)0.010 (2)0.021 (2)0.019 (2)
C200.055 (4)0.049 (4)0.054 (4)0.021 (3)0.035 (3)0.024 (3)
C210.047 (4)0.081 (5)0.082 (5)0.020 (4)0.043 (4)0.040 (4)
C220.026 (3)0.098 (7)0.078 (5)0.006 (4)0.012 (3)0.025 (5)
C230.043 (4)0.065 (5)0.052 (4)0.006 (3)0.012 (3)0.016 (3)
C240.035 (3)0.037 (3)0.040 (3)0.015 (2)0.017 (2)0.020 (2)
C250.050 (4)0.064 (4)0.035 (3)0.023 (3)0.021 (3)0.026 (3)
C260.047 (4)0.058 (4)0.026 (3)0.015 (3)0.010 (2)0.009 (3)
C270.035 (3)0.038 (3)0.042 (3)0.001 (3)0.011 (2)0.011 (2)
C280.030 (3)0.045 (3)0.045 (3)0.011 (3)0.014 (2)0.019 (3)
C290.057 (4)0.062 (4)0.053 (4)0.035 (4)0.036 (3)0.018 (3)
C300.053 (4)0.048 (3)0.038 (3)0.024 (3)0.033 (3)0.016 (2)
C310.062 (4)0.053 (4)0.026 (3)0.031 (3)0.017 (3)0.014 (2)
C320.054 (4)0.043 (4)0.033 (3)0.014 (3)0.013 (3)0.001 (2)
C330.044 (4)0.036 (3)0.056 (4)0.011 (3)0.017 (3)0.015 (3)
C340.040 (3)0.042 (3)0.065 (4)0.014 (3)0.028 (3)0.024 (3)
C350.039 (3)0.053 (4)0.050 (3)0.012 (3)0.028 (3)0.014 (3)
C360.065 (4)0.048 (4)0.042 (3)0.016 (3)0.036 (3)0.021 (3)
C370.029 (3)0.041 (3)0.046 (3)0.013 (3)0.010 (2)0.010 (2)
C380.042 (4)0.049 (4)0.059 (4)0.015 (3)0.021 (3)0.019 (3)
C390.067 (5)0.078 (5)0.081 (5)0.033 (4)0.052 (4)0.041 (4)
C400.030 (4)0.105 (7)0.107 (7)0.022 (4)0.033 (4)0.046 (6)
C410.029 (3)0.052 (4)0.076 (5)0.006 (3)0.006 (3)0.025 (3)
C420.027 (3)0.026 (3)0.060 (4)0.010 (2)0.010 (2)0.016 (2)
C430.028 (3)0.029 (3)0.046 (3)0.010 (2)0.014 (2)0.019 (2)
C440.045 (4)0.063 (4)0.042 (3)0.018 (3)0.017 (3)0.016 (3)
C450.089 (6)0.091 (6)0.079 (5)0.041 (5)0.063 (5)0.033 (5)
C460.033 (4)0.103 (7)0.086 (5)0.021 (4)0.032 (4)0.017 (5)
C470.027 (3)0.066 (5)0.057 (4)0.013 (3)0.009 (3)0.015 (3)
C480.036 (3)0.032 (3)0.046 (3)0.016 (2)0.018 (2)0.018 (2)
Geometric parameters (Å, º) top
Ba1—O82.676 (4)C7—H7A0.9700
Ba1—O112.725 (4)C7—H7B0.9700
Ba1—O72.836 (4)C8—H8A0.9700
Ba1—O42.886 (4)C8—H8B0.9700
Ba1—O32.919 (4)C9—C101.493 (8)
Ba1—O122.930 (5)C9—H9A0.9700
Ba1—O12.943 (3)C9—H9B0.9700
Ba1—O22.969 (4)C10—H10A0.9700
Ba1—O93.048 (5)C10—H10B0.9700
Ba1—O63.048 (4)C11—C121.510 (8)
Ba1—O53.057 (4)C11—H11A0.9700
Ba2—O202.710 (4)C11—H11B0.9700
Ba2—O182.836 (4)C12—H12A0.9700
Ba2—O162.841 (4)C12—H12B0.9700
Ba2—O142.846 (3)C13—C141.3900
Ba2—O172.868 (3)C13—C181.3900
Ba2—O192.871 (4)C14—C151.3900
Ba2—O252.876 (4)C14—H140.9300
Ba2—O152.877 (4)C15—C161.3900
Ba2—O242.890 (4)C15—H150.9300
Ba2—O212.982 (5)C16—C171.3900
N1—O101.230 (6)C16—H160.9300
N1—O91.245 (6)C17—C181.3900
N1—C241.431 (5)C17—H170.9300
N2—O121.203 (7)C19—C201.3900
N2—O131.211 (7)C19—C241.3900
N2—C181.451 (6)C20—C211.3900
N3—O221.209 (8)C20—H200.9300
N3—O231.242 (7)C21—C221.3900
N3—C421.427 (6)C21—H210.9300
N4—O271.206 (6)C22—C231.3900
N4—O281.244 (7)C22—H220.9300
N4—C481.417 (6)C23—C241.3900
O1—C121.416 (6)C23—H230.9300
O1—C11.440 (6)C25—C261.520 (9)
O2—C31.433 (6)C25—H25A0.9700
O2—C21.434 (7)C25—H25B0.9700
O3—C51.428 (7)C26—H26A0.9700
O3—C41.431 (7)C26—H26B0.9700
O4—C61.435 (7)C27—C281.483 (8)
O4—C71.475 (7)C27—H27A0.9700
O5—C81.425 (7)C27—H27B0.9700
O5—C91.446 (7)C28—H28A0.9700
O6—C111.423 (6)C28—H28B0.9700
O6—C101.425 (6)C29—C301.468 (8)
O7—H1W10.9000C29—H29A0.9700
O7—H2W10.9001C29—H29B0.9700
O8—C191.358 (5)C30—H30A0.9700
O11—C131.337 (4)C30—H30B0.9700
O14—C251.392 (7)C31—C321.463 (9)
O14—C361.452 (7)C31—H31A0.9700
O15—C261.426 (6)C31—H31B0.9700
O15—C271.449 (7)C32—H32A0.9700
O16—C291.420 (7)C32—H32B0.9700
O16—C281.450 (6)C33—C341.494 (8)
O17—C311.437 (7)C33—H33A0.9700
O17—C301.442 (7)C33—H33B0.9700
O18—C321.427 (7)C34—H34A0.9700
O18—C331.436 (7)C34—H34B0.9700
O19—C341.413 (7)C35—C361.476 (9)
O19—C351.416 (7)C35—H35A0.9700
O20—H1W20.9002C35—H35B0.9700
O20—H2W20.9000C36—H36A0.9700
O21—C371.338 (5)C36—H36B0.9700
O24—H1W30.9001C37—C381.3900
O24—H2W30.8999C37—C421.3900
O25—H1W40.9000C38—C391.3900
O25—H2W40.9001C38—H380.9300
O26—C431.340 (4)C39—C401.3900
C1—C21.495 (8)C39—H390.9300
C1—H1A0.9700C40—C411.3900
C1—H1B0.9700C40—H400.9300
C2—H2A0.9700C41—C421.3900
C2—H2B0.9700C41—H410.9300
C3—C41.494 (8)C43—C441.3900
C3—H3A0.9700C43—C481.3900
C3—H3B0.9700C44—C451.3900
C4—H4A0.9700C44—H440.9300
C4—H4B0.9700C45—C461.3900
C5—C61.433 (9)C45—H450.9300
C5—H5A0.9700C46—C471.3900
C5—H5B0.9700C46—H460.9300
C6—H6A0.9700C47—C481.3900
C6—H6B0.9700C47—H470.9300
C7—C81.450 (9)
O8—Ba1—O1191.40 (13)C6—C5—H5A109.5
O8—Ba1—O7135.99 (12)O3—C5—H5B109.5
O11—Ba1—O7132.56 (12)C6—C5—H5B109.5
O8—Ba1—O476.35 (12)H5A—C5—H5B108.1
O11—Ba1—O4122.88 (12)C5—C6—O4110.7 (5)
O7—Ba1—O476.73 (12)C5—C6—H6A109.5
O8—Ba1—O375.05 (12)O4—C6—H6A109.5
O11—Ba1—O3166.02 (12)C5—C6—H6B109.5
O7—Ba1—O361.19 (12)O4—C6—H6B109.5
O4—Ba1—O357.86 (11)H6A—C6—H6B108.1
O8—Ba1—O1271.77 (13)C8—C7—O4110.8 (5)
O11—Ba1—O1256.46 (12)C8—C7—H7A109.5
O7—Ba1—O12126.08 (13)O4—C7—H7A109.5
O4—Ba1—O1266.81 (11)C8—C7—H7B109.5
O3—Ba1—O12120.28 (11)O4—C7—H7B109.5
O8—Ba1—O1127.92 (11)H7A—C7—H7B108.1
O11—Ba1—O183.78 (11)O5—C8—C7110.3 (5)
O7—Ba1—O169.41 (12)O5—C8—H8A109.6
O4—Ba1—O1146.04 (11)C7—C8—H8A109.6
O3—Ba1—O1101.72 (10)O5—C8—H8B109.6
O12—Ba1—O1137.79 (11)C7—C8—H8B109.6
O8—Ba1—O280.30 (12)H8A—C8—H8B108.1
O11—Ba1—O2118.68 (11)O5—C9—C10110.3 (4)
O7—Ba1—O279.57 (11)O5—C9—H9A109.6
O4—Ba1—O2113.79 (11)C10—C9—H9A109.6
O3—Ba1—O256.45 (10)O5—C9—H9B109.6
O12—Ba1—O2151.16 (12)C10—C9—H9B109.6
O1—Ba1—O258.12 (10)H9A—C9—H9B108.1
O8—Ba1—O955.42 (11)O6—C10—C9107.5 (4)
O11—Ba1—O966.41 (11)O6—C10—H10A110.2
O7—Ba1—O9135.96 (12)C9—C10—H10A110.2
O4—Ba1—O9131.66 (11)O6—C10—H10B110.2
O3—Ba1—O9102.22 (11)C9—C10—H10B110.2
O12—Ba1—O997.82 (12)H10A—C10—H10B108.5
O1—Ba1—O975.69 (11)O6—C11—C12108.1 (4)
O2—Ba1—O959.16 (11)O6—C11—H11A110.1
O8—Ba1—O6165.08 (12)C12—C11—H11A110.1
O11—Ba1—O674.46 (12)O6—C11—H11B110.1
O7—Ba1—O658.14 (11)C12—C11—H11B110.1
O4—Ba1—O6107.10 (11)H11A—C11—H11B108.4
O3—Ba1—O6119.33 (11)O1—C12—C11109.4 (4)
O12—Ba1—O695.93 (12)O1—C12—H12A109.8
O1—Ba1—O656.40 (10)C11—C12—H12A109.8
O2—Ba1—O6110.42 (10)O1—C12—H12B109.8
O9—Ba1—O6120.31 (10)C11—C12—H12B109.8
O8—Ba1—O5121.75 (11)H12A—C12—H12B108.2
O11—Ba1—O586.61 (11)O11—C13—C14116.1 (3)
O7—Ba1—O568.04 (11)O11—C13—C18123.8 (3)
O4—Ba1—O557.42 (11)C14—C13—C18120.0
O3—Ba1—O5103.29 (10)C13—C14—C15120.0
O12—Ba1—O559.17 (11)C13—C14—H14120.0
O1—Ba1—O5109.72 (10)C15—C14—H14120.0
O2—Ba1—O5147.53 (10)C16—C15—C14120.0
O9—Ba1—O5152.08 (10)C16—C15—H15120.0
O6—Ba1—O553.96 (10)C14—C15—H15120.0
O20—Ba2—O1884.63 (12)C15—C16—C17120.0
O20—Ba2—O1680.60 (12)C15—C16—H16120.0
O18—Ba2—O16118.35 (10)C17—C16—H16120.0
O20—Ba2—O1475.42 (12)C18—C17—C16120.0
O18—Ba2—O14116.35 (11)C18—C17—H17120.0
O16—Ba2—O14116.83 (11)C16—C17—H17120.0
O20—Ba2—O1774.96 (12)C17—C18—C13120.0
O18—Ba2—O1759.39 (11)C17—C18—N2116.8 (3)
O16—Ba2—O1758.96 (11)C13—C18—N2122.8 (3)
O14—Ba2—O17150.35 (11)O8—C19—C20116.0 (3)
O20—Ba2—O1973.06 (13)O8—C19—C24124.0 (3)
O18—Ba2—O1957.77 (11)C20—C19—C24120.0
O16—Ba2—O19153.57 (11)C19—C20—C21120.0
O14—Ba2—O1958.64 (11)C19—C20—H20120.0
O17—Ba2—O19110.64 (11)C21—C20—H20120.0
O20—Ba2—O25140.80 (12)C20—C21—C22120.0
O18—Ba2—O25129.64 (11)C20—C21—H21120.0
O16—Ba2—O2594.82 (11)C22—C21—H21120.0
O14—Ba2—O2572.16 (11)C23—C22—C21120.0
O17—Ba2—O25135.16 (11)C23—C22—H22120.0
O19—Ba2—O25106.84 (11)C21—C22—H22120.0
O20—Ba2—O1571.43 (12)C24—C23—C22120.0
O18—Ba2—O15156.06 (11)C24—C23—H23120.0
O16—Ba2—O1558.14 (10)C22—C23—H23120.0
O14—Ba2—O1558.93 (11)C23—C24—C19120.0
O17—Ba2—O15111.72 (10)C23—C24—N1116.1 (3)
O19—Ba2—O15113.44 (11)C19—C24—N1123.9 (3)
O25—Ba2—O1573.22 (10)O14—C25—C26110.1 (5)
O20—Ba2—O24139.13 (12)O14—C25—H25A109.6
O18—Ba2—O2487.15 (11)C26—C25—H25A109.6
O16—Ba2—O2468.49 (10)O14—C25—H25B109.6
O14—Ba2—O24142.31 (11)C26—C25—H25B109.6
O17—Ba2—O2466.49 (10)H25A—C25—H25B108.2
O19—Ba2—O24132.84 (11)O15—C26—C25107.9 (5)
O25—Ba2—O2470.19 (10)O15—C26—H26A110.1
O15—Ba2—O24110.40 (11)C25—C26—H26A110.1
O20—Ba2—O21155.03 (14)O15—C26—H26B110.1
O18—Ba2—O2175.54 (12)C25—C26—H26B110.1
O16—Ba2—O21122.14 (13)H26A—C26—H26B108.4
O14—Ba2—O2199.77 (12)O15—C27—C28108.5 (4)
O17—Ba2—O21106.55 (12)O15—C27—H27A110.0
O19—Ba2—O2183.47 (13)C28—C27—H27A110.0
O25—Ba2—O2154.37 (11)O15—C27—H27B110.0
O15—Ba2—O21127.58 (11)C28—C27—H27B110.0
O24—Ba2—O2155.81 (12)H27A—C27—H27B108.4
O10—N1—O9121.1 (5)O16—C28—C27109.8 (4)
O10—N1—C24118.9 (5)O16—C28—H28A109.7
O9—N1—C24120.0 (4)C27—C28—H28A109.7
O12—N2—O13121.8 (6)O16—C28—H28B109.7
O12—N2—C18120.9 (5)C27—C28—H28B109.7
O13—N2—C18117.3 (6)H28A—C28—H28B108.2
O22—N3—O23120.7 (7)O16—C29—C30109.9 (4)
O22—N3—C42120.5 (5)O16—C29—H29A109.7
O23—N3—C42118.8 (6)C30—C29—H29A109.7
O27—N4—O28120.4 (5)O16—C29—H29B109.7
O27—N4—C48121.0 (5)C30—C29—H29B109.7
O28—N4—C48118.6 (5)H29A—C29—H29B108.2
C12—O1—C1109.0 (4)O17—C30—C29108.8 (5)
C12—O1—Ba1120.4 (3)O17—C30—H30A109.9
C1—O1—Ba1118.9 (3)C29—C30—H30A109.9
C3—O2—C2113.0 (4)O17—C30—H30B109.9
C3—O2—Ba1114.9 (3)C29—C30—H30B109.9
C2—O2—Ba1113.1 (3)H30A—C30—H30B108.3
C5—O3—C4113.9 (4)O17—C31—C32108.6 (5)
C5—O3—Ba1115.8 (3)O17—C31—H31A110.0
C4—O3—Ba1119.9 (3)C32—C31—H31A110.0
C6—O4—C7114.8 (4)O17—C31—H31B110.0
C6—O4—Ba1116.1 (3)C32—C31—H31B110.0
C7—O4—Ba1116.1 (3)H31A—C31—H31B108.4
C8—O5—C9111.7 (4)O18—C32—C31110.4 (5)
C8—O5—Ba1114.4 (3)O18—C32—H32A109.6
C9—O5—Ba1121.0 (3)C31—C32—H32A109.6
C11—O6—C10113.2 (4)O18—C32—H32B109.6
C11—O6—Ba1109.1 (3)C31—C32—H32B109.6
C10—O6—Ba1116.6 (3)H32A—C32—H32B108.1
Ba1—O7—H1W1120.3O18—C33—C34109.9 (5)
Ba1—O7—H2W1119.7O18—C33—H33A109.7
H1W1—O7—H2W1120.0C34—C33—H33A109.7
C19—O8—Ba1130.5 (3)O18—C33—H33B109.7
N1—O9—Ba1132.7 (3)C34—C33—H33B109.7
C13—O11—Ba1132.3 (3)H33A—C33—H33B108.2
N2—O12—Ba1131.9 (4)O19—C34—C33109.0 (5)
C25—O14—C36110.7 (4)O19—C34—H34A109.9
C25—O14—Ba2118.5 (3)C33—C34—H34A109.9
C36—O14—Ba2116.4 (3)O19—C34—H34B109.9
C26—O15—C27112.4 (4)C33—C34—H34B109.9
C26—O15—Ba2111.6 (3)H34A—C34—H34B108.3
C27—O15—Ba2111.8 (3)O19—C35—C36108.1 (5)
C29—O16—C28112.2 (4)O19—C35—H35A110.1
C29—O16—Ba2117.6 (3)C36—C35—H35A110.1
C28—O16—Ba2120.5 (3)O19—C35—H35B110.1
C31—O17—C30112.7 (4)C36—C35—H35B110.1
C31—O17—Ba2109.0 (3)H35A—C35—H35B108.4
C30—O17—Ba2112.5 (3)O14—C36—C35109.4 (5)
C32—O18—C33111.1 (4)O14—C36—H36A109.8
C32—O18—Ba2117.1 (3)C35—C36—H36A109.8
C33—O18—Ba2120.6 (3)O14—C36—H36B109.8
C34—O19—C35113.6 (4)C35—C36—H36B109.8
C34—O19—Ba2115.6 (3)H36A—C36—H36B108.2
C35—O19—Ba2115.2 (3)O21—C37—C38118.3 (3)
Ba2—O20—H1W2120.0O21—C37—C42121.6 (3)
Ba2—O20—H2W2120.0C38—C37—C42120.0
H1W2—O20—H2W2120.0C37—C38—C39120.0
C37—O21—Ba2131.7 (4)C37—C38—H38120.0
Ba2—O24—H1W3120.0C39—C38—H38120.0
Ba2—O24—H2W3120.0C40—C39—C38120.0
H1W3—O24—H2W3120.0C40—C39—H39120.0
Ba2—O25—H1W4120.0C38—C39—H39120.0
Ba2—O25—H2W4120.0C41—C40—C39120.0
H1W4—O25—H2W4120.0C41—C40—H40120.0
O1—C1—C2108.2 (5)C39—C40—H40120.0
O1—C1—H1A110.1C42—C41—C40120.0
C2—C1—H1A110.1C42—C41—H41120.0
O1—C1—H1B110.1C40—C41—H41120.0
C2—C1—H1B110.1C41—C42—C37120.0
H1A—C1—H1B108.4C41—C42—N3116.6 (3)
O2—C2—C1114.0 (5)C37—C42—N3123.4 (3)
O2—C2—H2A108.8O26—C43—C44118.1 (3)
C1—C2—H2A108.8O26—C43—C48121.9 (3)
O2—C2—H2B108.8C44—C43—C48120.0
C1—C2—H2B108.8C45—C44—C43120.0
H2A—C2—H2B107.7C45—C44—H44120.0
O2—C3—C4108.8 (4)C43—C44—H44120.0
O2—C3—H3A109.9C44—C45—C46120.0
C4—C3—H3A109.9C44—C45—H45120.0
O2—C3—H3B109.9C46—C45—H45120.0
C4—C3—H3B109.9C47—C46—C45120.0
H3A—C3—H3B108.3C47—C46—H46120.0
O3—C4—C3107.5 (4)C45—C46—H46120.0
O3—C4—H4A110.2C48—C47—C46120.0
C3—C4—H4A110.2C48—C47—H47120.0
O3—C4—H4B110.2C46—C47—H47120.0
C3—C4—H4B110.2C47—C48—C43120.0
H4A—C4—H4B108.5C47—C48—N4116.2 (3)
O3—C5—C6110.7 (5)C43—C48—N4123.8 (3)
O3—C5—H5A109.5
O8—Ba1—O1—C12165.6 (4)O17—Ba2—O16—C299.4 (4)
O11—Ba1—O1—C1278.7 (4)O19—Ba2—O16—C2963.9 (5)
O7—Ba1—O1—C1261.4 (4)O25—Ba2—O16—C29150.7 (4)
O4—Ba1—O1—C1265.9 (4)O15—Ba2—O16—C29142.5 (4)
O3—Ba1—O1—C12114.3 (4)O24—Ba2—O16—C2984.2 (4)
O12—Ba1—O1—C1260.1 (4)O21—Ba2—O16—C29100.3 (4)
O2—Ba1—O1—C12151.8 (4)O20—Ba2—O16—C2874.7 (4)
O9—Ba1—O1—C12145.9 (4)O18—Ba2—O16—C28153.4 (3)
O6—Ba1—O1—C123.3 (4)O14—Ba2—O16—C286.4 (4)
O5—Ba1—O1—C125.4 (4)O17—Ba2—O16—C28152.7 (4)
O8—Ba1—O1—C155.3 (4)O19—Ba2—O16—C2879.4 (4)
O11—Ba1—O1—C1142.2 (4)O25—Ba2—O16—C2866.0 (4)
O7—Ba1—O1—C177.7 (4)O15—Ba2—O16—C280.8 (3)
O4—Ba1—O1—C173.1 (4)O24—Ba2—O16—C28132.5 (4)
O3—Ba1—O1—C124.8 (4)O21—Ba2—O16—C28116.4 (4)
O12—Ba1—O1—C1160.9 (4)O20—Ba2—O17—C31122.5 (4)
O2—Ba1—O1—C112.7 (4)O18—Ba2—O17—C3129.8 (3)
O9—Ba1—O1—C175.0 (4)O16—Ba2—O17—C31149.5 (4)
O6—Ba1—O1—C1142.4 (4)O14—Ba2—O17—C31120.0 (4)
O5—Ba1—O1—C1133.7 (4)O19—Ba2—O17—C3157.6 (4)
O8—Ba1—O2—C399.8 (4)O25—Ba2—O17—C3187.3 (4)
O11—Ba1—O2—C3173.9 (3)O15—Ba2—O17—C31175.0 (3)
O7—Ba1—O2—C340.8 (3)O24—Ba2—O17—C3171.4 (3)
O4—Ba1—O2—C329.5 (4)O21—Ba2—O17—C3131.6 (4)
O3—Ba1—O2—C321.4 (3)O20—Ba2—O17—C30111.8 (3)
O12—Ba1—O2—C3114.3 (4)O18—Ba2—O17—C30155.6 (4)
O1—Ba1—O2—C3113.0 (4)O16—Ba2—O17—C3023.8 (3)
O9—Ba1—O2—C3155.2 (4)O14—Ba2—O17—C30114.2 (4)
O6—Ba1—O2—C390.9 (3)O19—Ba2—O17—C30176.7 (3)
O5—Ba1—O2—C336.7 (4)O25—Ba2—O17—C3038.4 (4)
O8—Ba1—O2—C2128.3 (4)O15—Ba2—O17—C3049.3 (3)
O11—Ba1—O2—C242.1 (4)O24—Ba2—O17—C3054.4 (3)
O7—Ba1—O2—C291.0 (4)O21—Ba2—O17—C3094.1 (3)
O4—Ba1—O2—C2161.4 (3)O20—Ba2—O18—C3273.0 (4)
O3—Ba1—O2—C2153.2 (4)O16—Ba2—O18—C323.3 (4)
O12—Ba1—O2—C2113.9 (4)O14—Ba2—O18—C32143.8 (4)
O1—Ba1—O2—C218.9 (3)O17—Ba2—O18—C322.7 (3)
O9—Ba1—O2—C273.0 (4)O19—Ba2—O18—C32146.4 (4)
O6—Ba1—O2—C240.9 (4)O25—Ba2—O18—C32128.1 (4)
O5—Ba1—O2—C295.1 (4)O15—Ba2—O18—C3271.5 (5)
O8—Ba1—O3—C568.6 (4)O24—Ba2—O18—C3266.9 (4)
O11—Ba1—O3—C583.0 (6)O21—Ba2—O18—C32122.3 (4)
O7—Ba1—O3—C5106.6 (4)O20—Ba2—O18—C3367.5 (4)
O4—Ba1—O3—C514.5 (4)O16—Ba2—O18—C33143.8 (4)
O12—Ba1—O3—C510.7 (4)O14—Ba2—O18—C333.3 (4)
O1—Ba1—O3—C5165.0 (4)O17—Ba2—O18—C33143.2 (4)
O2—Ba1—O3—C5156.7 (4)O19—Ba2—O18—C335.8 (4)
O9—Ba1—O3—C5117.4 (4)O25—Ba2—O18—C3391.4 (4)
O6—Ba1—O3—C5107.1 (4)O15—Ba2—O18—C3369.0 (5)
O5—Ba1—O3—C551.2 (4)O24—Ba2—O18—C33152.6 (4)
O8—Ba1—O3—C474.5 (4)O21—Ba2—O18—C3397.2 (4)
O11—Ba1—O3—C460.0 (6)O20—Ba2—O19—C34120.2 (4)
O7—Ba1—O3—C4110.4 (4)O18—Ba2—O19—C3425.8 (3)
O4—Ba1—O3—C4157.5 (4)O16—Ba2—O19—C34115.4 (4)
O12—Ba1—O3—C4132.4 (4)O14—Ba2—O19—C34156.8 (4)
O1—Ba1—O3—C452.0 (4)O17—Ba2—O19—C3454.1 (4)
O2—Ba1—O3—C413.7 (4)O25—Ba2—O19—C34100.8 (4)
O9—Ba1—O3—C425.7 (4)O15—Ba2—O19—C34179.4 (3)
O6—Ba1—O3—C4109.9 (4)O24—Ba2—O19—C3422.5 (4)
O5—Ba1—O3—C4165.8 (4)O21—Ba2—O19—C3451.2 (4)
O8—Ba1—O4—C698.0 (4)O20—Ba2—O19—C35104.1 (4)
O11—Ba1—O4—C6179.3 (4)O18—Ba2—O19—C35161.6 (4)
O7—Ba1—O4—C646.8 (4)O16—Ba2—O19—C35108.9 (4)
O3—Ba1—O4—C617.3 (4)O14—Ba2—O19—C3521.1 (3)
O12—Ba1—O4—C6173.8 (4)O17—Ba2—O19—C35170.2 (3)
O1—Ba1—O4—C642.5 (5)O25—Ba2—O19—C3534.9 (4)
O2—Ba1—O4—C625.3 (4)O15—Ba2—O19—C3543.7 (4)
O9—Ba1—O4—C694.3 (4)O24—Ba2—O19—C35113.2 (4)
O6—Ba1—O4—C697.0 (4)O21—Ba2—O19—C3584.6 (4)
O5—Ba1—O4—C6119.1 (4)O20—Ba2—O21—C3710.0 (6)
O8—Ba1—O4—C7122.4 (4)O18—Ba2—O21—C3748.5 (4)
O11—Ba1—O4—C739.7 (4)O16—Ba2—O21—C37163.2 (4)
O7—Ba1—O4—C792.7 (4)O14—Ba2—O21—C3766.4 (4)
O3—Ba1—O4—C7156.8 (4)O17—Ba2—O21—C3799.8 (4)
O12—Ba1—O4—C746.7 (4)O19—Ba2—O21—C379.8 (4)
O1—Ba1—O4—C797.1 (4)O25—Ba2—O21—C37126.0 (5)
O2—Ba1—O4—C7164.8 (4)O15—Ba2—O21—C37124.5 (4)
O9—Ba1—O4—C7126.1 (4)O24—Ba2—O21—C37145.0 (5)
O6—Ba1—O4—C742.5 (4)C12—O1—C1—C2175.8 (5)
O5—Ba1—O4—C720.5 (4)Ba1—O1—C1—C240.9 (6)
O8—Ba1—O5—C855.4 (4)C3—O2—C2—C182.5 (6)
O11—Ba1—O5—C8145.0 (4)Ba1—O2—C2—C150.3 (6)
O7—Ba1—O5—C876.1 (4)O1—C1—C2—O261.2 (7)
O4—Ba1—O5—C811.9 (4)C2—O2—C3—C4174.7 (5)
O3—Ba1—O5—C825.1 (4)Ba1—O2—C3—C453.4 (5)
O12—Ba1—O5—C892.5 (4)C5—O3—C4—C3171.3 (5)
O1—Ba1—O5—C8132.9 (4)Ba1—O3—C4—C345.0 (6)
O2—Ba1—O5—C871.7 (4)O2—C3—C4—O363.8 (6)
O9—Ba1—O5—C8130.5 (4)C4—O3—C5—C6169.5 (5)
O6—Ba1—O5—C8141.8 (4)Ba1—O3—C5—C645.3 (6)
O8—Ba1—O5—C9166.3 (4)O3—C5—C6—O462.1 (7)
O11—Ba1—O5—C976.7 (4)C7—O4—C6—C5171.6 (5)
O7—Ba1—O5—C962.2 (4)Ba1—O4—C6—C548.3 (6)
O4—Ba1—O5—C9150.2 (4)C6—O4—C7—C886.8 (6)
O3—Ba1—O5—C9113.3 (4)Ba1—O4—C7—C853.2 (6)
O12—Ba1—O5—C9129.2 (4)C9—O5—C8—C7174.8 (5)
O1—Ba1—O5—C95.4 (4)Ba1—O5—C8—C743.0 (6)
O2—Ba1—O5—C966.6 (4)O4—C7—C8—O564.1 (7)
O9—Ba1—O5—C991.2 (4)C8—O5—C9—C10172.7 (5)
O6—Ba1—O5—C93.5 (4)Ba1—O5—C9—C1033.4 (6)
O8—Ba1—O6—C1181.1 (5)C11—O6—C10—C9172.9 (5)
O11—Ba1—O6—C1162.1 (3)Ba1—O6—C10—C959.3 (5)
O7—Ba1—O6—C11115.9 (4)O5—C9—C10—O659.2 (6)
O4—Ba1—O6—C11177.6 (3)C10—O6—C11—C12165.9 (5)
O3—Ba1—O6—C11115.4 (3)Ba1—O6—C11—C1262.5 (5)
O12—Ba1—O6—C11114.9 (3)C1—O1—C12—C11177.6 (5)
O1—Ba1—O6—C1130.7 (3)Ba1—O1—C12—C1135.0 (6)
O2—Ba1—O6—C1153.2 (3)O6—C11—C12—O166.2 (6)
O9—Ba1—O6—C1112.2 (4)Ba1—O11—C13—C14135.5 (3)
O5—Ba1—O6—C11159.4 (4)Ba1—O11—C13—C1840.6 (5)
O8—Ba1—O6—C1048.7 (6)O11—C13—C14—C15176.3 (4)
O11—Ba1—O6—C1067.7 (3)C13—C14—C15—C160.0
O7—Ba1—O6—C10114.3 (4)C14—C15—C16—C170.0
O4—Ba1—O6—C1052.6 (3)C15—C16—C17—C180.0
O3—Ba1—O6—C10114.8 (3)C16—C17—C18—C130.0
O12—Ba1—O6—C1015.0 (3)C16—C17—C18—N2173.4 (4)
O1—Ba1—O6—C10160.6 (4)O11—C13—C18—C17176.0 (4)
O2—Ba1—O6—C10177.0 (3)C14—C13—C18—C170.0
O9—Ba1—O6—C10117.6 (3)O11—C13—C18—N211.0 (5)
O5—Ba1—O6—C1029.6 (3)C14—C13—C18—N2173.0 (4)
O11—Ba1—O8—C19118.6 (4)O12—N2—C18—C17177.7 (4)
O7—Ba1—O8—C1964.1 (4)O13—N2—C18—C170.5 (7)
O4—Ba1—O8—C19117.9 (4)O12—N2—C18—C139.0 (7)
O3—Ba1—O8—C1958.0 (4)O13—N2—C18—C13172.7 (6)
O12—Ba1—O8—C19172.4 (4)Ba1—O8—C19—C20123.0 (3)
O1—Ba1—O8—C1935.4 (4)Ba1—O8—C19—C2458.7 (5)
O2—Ba1—O8—C190.3 (4)O8—C19—C20—C21178.4 (4)
O9—Ba1—O8—C1958.8 (4)C24—C19—C20—C210.0
O6—Ba1—O8—C19136.8 (4)C19—C20—C21—C220.0
O5—Ba1—O8—C19154.6 (3)C20—C21—C22—C230.0
O10—N1—O9—Ba1148.7 (4)C21—C22—C23—C240.0
C24—N1—O9—Ba131.3 (7)C22—C23—C24—C190.0
O8—Ba1—O9—N149.1 (4)C22—C23—C24—N1179.4 (4)
O11—Ba1—O9—N1158.6 (5)O8—C19—C24—C23178.2 (4)
O7—Ba1—O9—N173.8 (5)C20—C19—C24—C230.0
O4—Ba1—O9—N144.7 (5)O8—C19—C24—N12.5 (5)
O3—Ba1—O9—N112.9 (5)C20—C19—C24—N1179.3 (4)
O12—Ba1—O9—N1110.5 (4)O10—N1—C24—C237.4 (6)
O1—Ba1—O9—N1112.1 (5)O9—N1—C24—C23172.7 (4)
O2—Ba1—O9—N150.9 (4)O10—N1—C24—C19173.2 (4)
O6—Ba1—O9—N1147.9 (4)O9—N1—C24—C196.7 (6)
O5—Ba1—O9—N1142.7 (4)C36—O14—C25—C26175.8 (5)
O8—Ba1—O11—C13119.2 (4)Ba2—O14—C25—C2637.5 (6)
O7—Ba1—O11—C1358.3 (4)C27—O15—C26—C25175.9 (5)
O4—Ba1—O11—C1344.6 (4)Ba2—O15—C26—C2557.6 (5)
O3—Ba1—O11—C13133.1 (5)O14—C25—C26—O1563.9 (7)
O12—Ba1—O11—C1352.2 (4)C26—O15—C27—C28172.9 (5)
O1—Ba1—O11—C13112.8 (4)Ba2—O15—C27—C2860.7 (5)
O2—Ba1—O11—C13161.1 (4)C29—O16—C28—C27173.8 (5)
O9—Ba1—O11—C13170.1 (4)Ba2—O16—C28—C2728.7 (6)
O6—Ba1—O11—C1356.0 (4)O15—C27—C28—O1658.6 (6)
O5—Ba1—O11—C132.5 (4)C28—O16—C29—C30172.7 (5)
O13—N2—O12—Ba1137.8 (6)Ba2—O16—C29—C3041.1 (6)
C18—N2—O12—Ba140.4 (8)C31—O17—C30—C29178.9 (4)
O8—Ba1—O12—N2159.3 (5)Ba2—O17—C30—C2955.2 (5)
O11—Ba1—O12—N254.9 (5)O16—C29—C30—O1764.2 (6)
O7—Ba1—O12—N266.5 (5)C30—O17—C31—C32172.6 (5)
O4—Ba1—O12—N2118.1 (5)Ba2—O17—C31—C3261.7 (5)
O3—Ba1—O12—N2141.1 (5)C33—O18—C32—C31178.8 (5)
O1—Ba1—O12—N232.5 (6)Ba2—O18—C32—C3134.7 (6)
O2—Ba1—O12—N2144.3 (5)O17—C31—C32—O1865.7 (6)
O9—Ba1—O12—N2109.8 (5)C32—O18—C33—C34176.8 (5)
O6—Ba1—O12—N212.0 (5)Ba2—O18—C33—C3434.2 (6)
O5—Ba1—O12—N253.3 (5)C35—O19—C34—C33169.6 (5)
O20—Ba2—O14—C2570.4 (4)Ba2—O19—C34—C3354.0 (5)
O18—Ba2—O14—C25146.7 (4)O18—C33—C34—O1956.8 (6)
O16—Ba2—O14—C250.9 (4)C34—O19—C35—C36170.9 (5)
O17—Ba2—O14—C2572.8 (5)Ba2—O19—C35—C3652.5 (6)
O19—Ba2—O14—C25149.2 (4)C25—O14—C36—C35175.8 (5)
O25—Ba2—O14—C2587.3 (4)Ba2—O14—C36—C3545.1 (6)
O15—Ba2—O14—C256.5 (4)O19—C35—C36—O1464.2 (6)
O24—Ba2—O14—C2589.9 (4)Ba2—O21—C37—C3894.1 (4)
O21—Ba2—O14—C25134.7 (4)Ba2—O21—C37—C4282.6 (5)
O20—Ba2—O14—C3665.6 (4)O21—C37—C38—C39176.8 (5)
O18—Ba2—O14—C3610.7 (4)C42—C37—C38—C390.0
O16—Ba2—O14—C36136.9 (4)C37—C38—C39—C400.0
O17—Ba2—O14—C3663.1 (4)C38—C39—C40—C410.0
O19—Ba2—O14—C3613.2 (4)C39—C40—C41—C420.0
O25—Ba2—O14—C36136.8 (4)C40—C41—C42—C370.0
O15—Ba2—O14—C36142.4 (4)C40—C41—C42—N3179.6 (4)
O24—Ba2—O14—C36134.1 (4)O21—C37—C42—C41176.6 (5)
O21—Ba2—O14—C3689.3 (4)C38—C37—C42—C410.0
O20—Ba2—O15—C26111.4 (4)O21—C37—C42—N33.8 (6)
O18—Ba2—O15—C26112.9 (4)C38—C37—C42—N3179.6 (4)
O16—Ba2—O15—C26158.3 (4)O22—N3—C42—C41147.1 (5)
O14—Ba2—O15—C2627.5 (3)O23—N3—C42—C4131.0 (6)
O17—Ba2—O15—C26176.0 (3)O22—N3—C42—C3732.5 (7)
O19—Ba2—O15—C2650.1 (4)O23—N3—C42—C37149.4 (4)
O25—Ba2—O15—C2651.4 (4)O26—C43—C44—C45178.4 (4)
O24—Ba2—O15—C26112.1 (4)C48—C43—C44—C450.0
O21—Ba2—O15—C2650.1 (4)C43—C44—C45—C460.0
O20—Ba2—O15—C27121.8 (4)C44—C45—C46—C470.0
O18—Ba2—O15—C27120.2 (4)C45—C46—C47—C480.0
O16—Ba2—O15—C2731.5 (3)C46—C47—C48—C430.0
O14—Ba2—O15—C27154.4 (4)C46—C47—C48—N4178.8 (4)
O17—Ba2—O15—C2757.2 (4)O26—C43—C48—C47178.4 (4)
O19—Ba2—O15—C27176.9 (3)C44—C43—C48—C470.0
O25—Ba2—O15—C2775.4 (3)O26—C43—C48—N42.9 (5)
O24—Ba2—O15—C2714.7 (4)C44—C43—C48—N4178.7 (4)
O21—Ba2—O15—C2776.7 (4)O27—N4—C48—C47155.0 (5)
O20—Ba2—O16—C2968.6 (4)O28—N4—C48—C4727.5 (6)
O18—Ba2—O16—C2910.0 (4)O27—N4—C48—C4323.8 (7)
O14—Ba2—O16—C29136.9 (4)O28—N4—C48—C43153.7 (5)

Experimental details

Crystal data
Chemical formula[Ba(C12H24O6)(C6H4NO3)(H2O)3](C6H4NO3)[Ba(C12H24O6)(C6H4N O3)2(H2O)]
Mr1427.78
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)13.7492 (3), 14.9672 (3), 16.8669 (3)
α, β, γ (°)97.9362 (2), 109.7546 (7), 108.8642 (7)
V3)2969.6 (1)
Z2
Radiation typeMo Kα
µ (mm1)1.41
Crystal size (mm)0.24 × 0.22 × 0.20
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.729, 0.766
No. of measured, independent and
observed [I > 2σ(I)] reflections
17916, 13455, 10337
Rint0.081
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.171, 0.96
No. of reflections13455
No. of parameters692
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)2.47, 2.90

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O2—C21.434 (7)C1—C21.495 (8)
O1—C1—C2108.2 (5)O2—C2—C1114.0 (5)
O1—C1—C2—O261.2 (7)
Hydrogen-bonding and short-contact geometry (Å, °) top
D-H···AD-HH···AD···AD-H···A
O7-H21W···O26ii0.902.042.838 (7)147
O20-H12W···O11i0.902.232.953 (6)138
O20-H12W···O12i0.902.382.998 (6)126
O20-H22W···O8i0.902.092.880 (7)146
O25-H24W···O27i0.902.273.012 (7)139
C3-H3A···O26ii0.972.593.485 (7)154
C36-H36A···O27iii0.972.503.296 (10)139
Symmetry codes: (i) x, y, z; (ii) x, y-1, z; (iii) -x, 1-y, 1-z
 

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