Two novel alkaline earth coordination polymers constructed from cinnamic acid and 1,10-phenanthroline: synthesis and structural and thermal properties

In coordination chemistry and crystal engineering, many factors influence the construction of coordination polymers and the final frameworks depend greatly on the organic ligands used. The diverse coordination modes of N-donor ligands have been employed to assemble metal–organic frameworks. Carb­oxy­lic acid ligands can deprotonate completely or partially when bonding to metal ions and can also act as donors or acceptors of hydrogen bonds; they are thus good candidates for the construction of supra­molecular architectures. We synthesized under reflux or hydro­thermal conditions two new alkaline earth(II) complexes, namely poly[(1,10-phenanthroline-κ²N,N′)bis­(μ-3-phenyl­prop-2-enoato-κ³O,O′:O)calcium(II)], [Ca(C₁₀H₇O₂)₂(C₁₀H₈N₂)]_n, (1), and poly[(1,10-phenanthroline-κ²N,N′)(μ₃-3-phenyl­prop-2-enoato-κ⁴O:O,O′:O′)(μ-3-phenyl­prop-2-enoato-κ³O,O′:O)barium(II)], [Ba(C₁₀H₇O₂)₂(C₁₀H₈N₂)]_n, (2), and characterized them by FT–IR and UV–Vis spectroscopies, thermogravimetric analysis (TGA) and single-crystal X-ray diffraction analysis, as well as by powder X-ray diffraction (PXRD) analysis. Complex (1) features a chain topology of type 2,4 C4, where the Ca atoms are connected by O and N atoms, forming a distorted bicapped trigonal prismatic geometry. Complex (2) displays chains of topology type 2,3,5 C4, where the Ba atom is nine-coordinated by seven O atoms of bridging/chelating carboxyl­ate groups from two cinnamate ligands and by two N atoms from one phenanthroline ligand, forming a distorted tricapped prismatic arrangement. Weak C—H...O hydrogen bonds and π–π stacking inter­actions between phenanthroline ligands are responsible to the formation of a supra­molecular three-dimensional network. The thermal decompositions of (1) and (2) in the temperature range 297–1173 K revealed that they both decompose in three steps and transform to the corresponding metal oxide.

Computing details

For both structures, data collection: APEX2 (Bruker, 2011); cell refinement: APEX2 (Bruker, 2011); data reduction: APEX2 (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for Ca; SHELXT (Sheldrick, 2015) for Ba. For both structures, molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012) and CRYSCAL (T. Roisnel, local program).

Poly[(1,10-phenanthroline-κ²N,N')bis(µ-3-phenylprop-2-enoato-κ³O,O':O)calcium(I)] (Ca)

Crystal data

[Ca(C10H7O2)2(C10H8N2)]	F(000) = 1072
Mr = 514.58	Dx = 1.414 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1362 reflections
a = 27.0933 (11) Å	θ = 3.0–23.0°
b = 11.2988 (4) Å	µ = 0.30 mm^−1
c = 7.8989 (3) Å	T = 295 K
V = 2418.03 (16) Å^3	Prism, colorless
Z = 4	0.25 × 0.17 × 0.15 mm

Data collection

Bruker APEXII diffractometer	1617 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.061
CCD rotation images, thick slices scans	θmax = 27°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −31→34
Tmin = 0.672, Tmax = 0.746	k = −10→14
10605 measured reflections	l = −10→10
2587 independent reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0695P)^2 + 0.1557P] where P = (Fo^2 + 2Fc^2)/3
2585 reflections	(Δ/σ)max < 0.001
168 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.07507 (9)	0.5961 (2)	0.3964 (3)	0.0418 (6)
C2	−0.11192 (10)	0.6796 (2)	0.4654 (4)	0.0515 (7)
H2	−0.1031	0.7224	0.5613	0.062*
C3	−0.15583 (10)	0.6980 (2)	0.4023 (4)	0.0484 (7)
H3	−0.1648	0.6514	0.3103	0.058*
C4	−0.19290 (9)	0.7848 (2)	0.4610 (3)	0.0411 (6)
C5	−0.18367 (10)	0.8693 (2)	0.5833 (3)	0.0521 (7)
H5	−0.1533	0.8697	0.6382	0.063*
C6	−0.21802 (13)	0.9519 (3)	0.6248 (4)	0.0641 (9)
H6	−0.2104	1.0093	0.705	0.077*
C7	−0.26384 (12)	0.9521 (3)	0.5506 (4)	0.0644 (9)
H7	−0.2871	1.009	0.5801	0.077*
C8	−0.27482 (10)	0.8667 (3)	0.4316 (4)	0.0639 (9)
H8	−0.306	0.8641	0.3821	0.077*
C9	−0.23904 (10)	0.7846 (2)	0.3862 (4)	0.0534 (7)
H9	−0.2462	0.7284	0.3038	0.064*
C11	0.02276 (9)	0.1500 (2)	0.2029 (3)	0.0436 (6)
C12	0.04485 (12)	0.0408 (2)	0.1608 (4)	0.0552 (8)
C13	0.08922 (13)	0.0451 (3)	0.0717 (4)	0.0711 (10)
H13	0.1056	−0.0249	0.0453	0.085*
C14	0.10861 (11)	0.1497 (3)	0.0234 (4)	0.0686 (9)
H14	0.1378	0.1525	−0.0382	0.082*
C15	0.08385 (10)	0.2544 (3)	0.0679 (4)	0.0554 (7)
H15	0.0972	0.3263	0.0331	0.066*
C16	0.02101 (12)	−0.0679 (3)	0.2095 (4)	0.0712 (11)
H16	0.0359	−0.1397	0.1826	0.085*
Ca1	0	0.44729 (6)	0.25	0.0390 (2)
N1	0.04254 (8)	0.25573 (18)	0.1570 (3)	0.0456 (6)
O1	−0.03319 (6)	0.59409 (17)	0.4666 (2)	0.0552 (5)
O2	−0.08423 (8)	0.53279 (18)	0.2711 (3)	0.0637 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0369 (13)	0.0426 (14)	0.0458 (15)	0.0012 (11)	0.0001 (12)	0.0045 (12)
C2	0.0469 (16)	0.0558 (16)	0.0519 (17)	0.0055 (13)	0.0015 (13)	−0.0011 (13)
C3	0.0457 (15)	0.0458 (15)	0.0538 (16)	−0.0014 (12)	−0.0004 (13)	0.0009 (13)
C4	0.0362 (13)	0.0403 (13)	0.0467 (15)	−0.0007 (11)	0.0037 (11)	0.0055 (12)
C5	0.0473 (15)	0.0578 (17)	0.0513 (16)	−0.0050 (13)	0.0051 (13)	0.0004 (14)
C6	0.076 (2)	0.0515 (17)	0.065 (2)	−0.0042 (16)	0.0192 (18)	−0.0078 (15)
C7	0.064 (2)	0.0546 (18)	0.074 (2)	0.0212 (16)	0.0251 (17)	0.0180 (17)
C8	0.0399 (16)	0.079 (2)	0.073 (2)	0.0069 (15)	0.0026 (14)	0.0232 (19)
C9	0.0468 (16)	0.0526 (16)	0.0609 (18)	−0.0019 (13)	0.0017 (14)	−0.0041 (13)
C11	0.0465 (15)	0.0457 (15)	0.0387 (14)	0.0031 (12)	−0.0144 (12)	−0.0030 (11)
C12	0.0640 (19)	0.0530 (16)	0.0488 (17)	0.0115 (15)	−0.0191 (15)	−0.0087 (13)
C13	0.072 (2)	0.073 (2)	0.068 (2)	0.0259 (18)	−0.0170 (18)	−0.0219 (18)
C14	0.0492 (17)	0.094 (3)	0.062 (2)	0.0184 (18)	0.0006 (15)	−0.0211 (19)
C15	0.0433 (15)	0.069 (2)	0.0535 (17)	0.0035 (14)	0.0000 (13)	−0.0019 (14)
C16	0.095 (3)	0.0459 (16)	0.072 (2)	0.0126 (14)	−0.029 (2)	−0.0073 (15)
Ca1	0.0344 (4)	0.0420 (4)	0.0407 (4)	0	−0.0027 (3)	0
N1	0.0407 (12)	0.0518 (13)	0.0444 (13)	0.0033 (10)	−0.0026 (10)	−0.0017 (10)
O1	0.0445 (11)	0.0700 (12)	0.0512 (11)	0.0057 (9)	−0.0077 (9)	−0.0002 (9)
O2	0.0552 (12)	0.0676 (13)	0.0682 (14)	0.0123 (10)	−0.0097 (10)	−0.0243 (11)

Geometric parameters (Å, º)

C1—O2	1.246 (3)	C11—C11^i	1.440 (5)
C1—O1	1.263 (3)	C12—C13	1.394 (4)
C1—C2	1.478 (4)	C12—C16	1.439 (4)
C1—Ca1	2.881 (3)	C13—C14	1.349 (5)
C2—C3	1.307 (4)	C13—H13	0.93
C2—H2	0.93	C14—C15	1.405 (4)
C3—C4	1.478 (3)	C14—H14	0.93
C3—H3	0.93	C15—N1	1.322 (3)
C4—C5	1.381 (4)	C15—H15	0.93
C4—C9	1.383 (4)	C16—C16^i	1.306 (7)
C5—C6	1.358 (4)	C16—H16	0.93
C5—H5	0.93	Ca1—O1^ii	2.4575 (19)
C6—C7	1.373 (5)	Ca1—O1^iii	2.4575 (19)
C6—H6	0.93	Ca1—O1	2.5468 (19)
C7—C8	1.380 (5)	Ca1—O1^i	2.5468 (19)
C7—H7	0.93	Ca1—O2^i	2.484 (2)
C8—C9	1.389 (4)	Ca1—O2	2.484 (2)
C8—H8	0.93	Ca1—N1	2.560 (2)
C9—H9	0.93	Ca1—N1^i	2.560 (2)
C11—N1	1.359 (3)	Ca1—C1^i	2.881 (3)
C11—C12	1.411 (4)	O1—Ca1^ii	2.4575 (19)
O2—C1—O1	121.1 (2)	O2—Ca1—O1^i	96.67 (7)
O2—C1—C2	121.7 (2)	O1—Ca1—O1^i	98.72 (9)
O1—C1—C2	117.2 (2)	O1^ii—Ca1—N1	86.31 (7)
O2—C1—Ca1	59.13 (14)	O1^iii—Ca1—N1	75.08 (6)
O1—C1—Ca1	62.06 (13)	O2^i—Ca1—N1	84.03 (7)
C2—C1—Ca1	175.95 (18)	O2—Ca1—N1	139.63 (7)
C3—C2—C1	125.2 (3)	O1—Ca1—N1	154.47 (6)
C3—C2—H2	117.4	O1^i—Ca1—N1	101.48 (6)
C1—C2—H2	117.4	O1^ii—Ca1—N1^i	75.08 (6)
C2—C3—C4	127.2 (3)	O1^iii—Ca1—N1^i	86.31 (7)
C2—C3—H3	116.4	O2^i—Ca1—N1^i	139.63 (7)
C4—C3—H3	116.4	O2—Ca1—N1^i	84.03 (7)
C5—C4—C9	117.6 (2)	O1—Ca1—N1^i	101.48 (6)
C5—C4—C3	123.7 (2)	O1^i—Ca1—N1^i	154.47 (7)
C9—C4—C3	118.6 (2)	N1—Ca1—N1^i	64.54 (10)
C6—C5—C4	121.3 (3)	O1^ii—Ca1—C1^i	102.61 (7)
C6—C5—H5	119.3	O1^iii—Ca1—C1^i	90.21 (7)
C4—C5—H5	119.3	O2^i—Ca1—C1^i	25.50 (6)
C5—C6—C7	121.2 (3)	O2—Ca1—C1^i	116.65 (8)
C5—C6—H6	119.4	O1—Ca1—C1^i	97.97 (7)
C7—C6—H6	119.4	O1^i—Ca1—C1^i	25.99 (6)
C6—C7—C8	119.0 (3)	N1—Ca1—C1^i	93.46 (7)
C6—C7—H7	120.5	N1^i—Ca1—C1^i	157.89 (7)
C8—C7—H7	120.5	O1^ii—Ca1—C1	90.21 (7)
C7—C8—C9	119.5 (3)	O1^iii—Ca1—C1	102.61 (7)
C7—C8—H8	120.2	O2^i—Ca1—C1	116.65 (8)
C9—C8—H8	120.2	O2—Ca1—C1	25.50 (6)
C4—C9—C8	121.3 (3)	O1—Ca1—C1	25.99 (6)
C4—C9—H9	119.3	O1^i—Ca1—C1	97.97 (7)
C8—C9—H9	119.3	N1—Ca1—C1	157.89 (7)
N1—C11—C12	122.6 (2)	N1^i—Ca1—C1	93.46 (7)
N1—C11—C11^i	118.39 (14)	C1^i—Ca1—C1	108.60 (10)
C12—C11—C11^i	119.01 (17)	O1^ii—Ca1—Ca1^ii	35.19 (4)
C13—C12—C11	117.0 (3)	O1^iii—Ca1—Ca1^ii	157.99 (4)
C13—C12—C16	123.5 (3)	O2^i—Ca1—Ca1^ii	87.24 (5)
C11—C12—C16	119.5 (3)	O2—Ca1—Ca1^ii	79.83 (5)
C14—C13—C12	120.6 (3)	O1—Ca1—Ca1^ii	33.78 (4)
C14—C13—H13	119.7	O1^i—Ca1—Ca1^ii	117.07 (5)
C12—C13—H13	119.7	N1—Ca1—Ca1^ii	121.25 (5)
C13—C14—C15	118.8 (3)	N1^i—Ca1—Ca1^ii	88.25 (5)
C13—C14—H14	120.6	C1^i—Ca1—Ca1^ii	102.46 (6)
C15—C14—H14	120.6	C1—Ca1—Ca1^ii	56.45 (5)
N1—C15—C14	123.2 (3)	O1^ii—Ca1—Ca1^iv	157.99 (4)
N1—C15—H15	118.4	O1^iii—Ca1—Ca1^iv	35.19 (4)
C14—C15—H15	118.4	O2^i—Ca1—Ca1^iv	79.83 (5)
C16^i—C16—C12	121.47 (18)	O2—Ca1—Ca1^iv	87.24 (5)
C16^i—C16—H16	119.3	O1—Ca1—Ca1^iv	117.07 (5)
C12—C16—H16	119.3	O1^i—Ca1—Ca1^iv	33.78 (4)
O1^ii—Ca1—O1^iii	158.06 (10)	N1—Ca1—Ca1^iv	88.25 (5)
O1^ii—Ca1—O2^i	78.40 (6)	N1^i—Ca1—Ca1^iv	121.25 (5)
O1^iii—Ca1—O2^i	110.43 (7)	C1^i—Ca1—Ca1^iv	56.45 (5)
O1^ii—Ca1—O2	110.43 (7)	C1—Ca1—Ca1^iv	102.46 (6)
O1^iii—Ca1—O2	78.40 (6)	Ca1^ii—Ca1—Ca1^iv	146.43 (4)
O2^i—Ca1—O2	134.22 (10)	C15—N1—C11	117.8 (2)
O1^ii—Ca1—O1	68.97 (7)	C15—N1—Ca1	122.92 (19)
O1^iii—Ca1—O1	127.35 (7)	C11—N1—Ca1	119.31 (16)
O2^i—Ca1—O1	96.67 (7)	C1—O1—Ca1^ii	137.05 (17)
O2—Ca1—O1	51.48 (6)	C1—O1—Ca1	91.95 (15)
O1^ii—Ca1—O1^i	127.35 (7)	Ca1^ii—O1—Ca1	111.03 (7)
O1^iii—Ca1—O1^i	68.97 (7)	C1—O2—Ca1	95.37 (16)
O2^i—Ca1—O1^i	51.48 (6)
O2—C1—C2—C3	−2.0 (4)	O1^i—Ca1—N1—C15	23.0 (2)
O1—C1—C2—C3	175.8 (3)	N1^i—Ca1—N1—C15	−179.6 (2)
C1—C2—C3—C4	−176.5 (2)	C1^i—Ca1—N1—C15	−1.9 (2)
C2—C3—C4—C5	7.4 (4)	C1—Ca1—N1—C15	174.2 (2)
C2—C3—C4—C9	−174.9 (3)	Ca1^ii—Ca1—N1—C15	−108.77 (19)
C9—C4—C5—C6	−2.1 (4)	Ca1^iv—Ca1—N1—C15	54.29 (19)
C3—C4—C5—C6	175.7 (3)	O1^ii—Ca1—N1—C11	74.37 (17)
C4—C5—C6—C7	2.1 (4)	O1^iii—Ca1—N1—C11	−93.90 (17)
C5—C6—C7—C8	−0.1 (5)	O2^i—Ca1—N1—C11	153.08 (18)
C6—C7—C8—C9	−1.7 (5)	O2—Ca1—N1—C11	−43.3 (2)
C5—C4—C9—C8	0.2 (4)	O1—Ca1—N1—C11	60.1 (2)
C3—C4—C9—C8	−177.7 (3)	O1^i—Ca1—N1—C11	−158.23 (17)
C7—C8—C9—C4	1.7 (4)	N1^i—Ca1—N1—C11	−0.85 (12)
N1—C11—C12—C13	1.4 (4)	C1^i—Ca1—N1—C11	176.81 (17)
C11^i—C11—C12—C13	−179.1 (3)	C1—Ca1—N1—C11	−7.1 (3)
N1—C11—C12—C16	−178.2 (2)	Ca1^ii—Ca1—N1—C11	69.98 (18)
C11^i—C11—C12—C16	1.3 (4)	Ca1^iv—Ca1—N1—C11	−126.96 (17)
C11—C12—C13—C14	−2.4 (4)	O2—C1—O1—Ca1^ii	−122.0 (3)
C16—C12—C13—C14	177.1 (3)	C2—C1—O1—Ca1^ii	60.2 (3)
C12—C13—C14—C15	1.4 (5)	Ca1—C1—O1—Ca1^ii	−124.3 (2)
C13—C14—C15—N1	0.8 (4)	O2—C1—O1—Ca1	2.3 (3)
C13—C12—C16—C16^i	−178.8 (4)	C2—C1—O1—Ca1	−175.5 (2)
C11—C12—C16—C16^i	0.7 (6)	O1^ii—Ca1—O1—C1	−142.91 (18)
O2—C1—Ca1—O1^ii	−143.41 (17)	O1^iii—Ca1—O1—C1	20.18 (17)
O1—C1—Ca1—O1^ii	34.26 (17)	O2^i—Ca1—O1—C1	142.27 (15)
O2—C1—Ca1—O1^iii	18.65 (18)	O2—Ca1—O1—C1	−1.28 (14)
O1—C1—Ca1—O1^iii	−163.68 (13)	O1^i—Ca1—O1—C1	90.32 (15)
O2—C1—Ca1—O2^i	139.48 (15)	N1—Ca1—O1—C1	−127.64 (18)
O1—C1—Ca1—O2^i	−42.85 (17)	N1^i—Ca1—O1—C1	−73.98 (15)
O1—C1—Ca1—O2	177.7 (3)	C1^i—Ca1—O1—C1	116.59 (15)
O2—C1—Ca1—O1	−177.7 (3)	Ca1^ii—Ca1—O1—C1	−142.91 (18)
O2—C1—Ca1—O1^i	88.78 (17)	Ca1^iv—Ca1—O1—C1	60.31 (15)
O1—C1—Ca1—O1^i	−93.56 (16)	O1^ii—Ca1—O1—Ca1^ii	0
O2—C1—Ca1—N1	−62.7 (3)	O1^iii—Ca1—O1—Ca1^ii	163.08 (7)
O1—C1—Ca1—N1	115.0 (2)	O2^i—Ca1—O1—Ca1^ii	−74.82 (8)
O2—C1—Ca1—N1^i	−68.34 (17)	O2—Ca1—O1—Ca1^ii	141.62 (12)
O1—C1—Ca1—N1^i	109.33 (15)	O1^i—Ca1—O1—Ca1^ii	−126.77 (9)
O2—C1—Ca1—C1^i	113.20 (18)	N1—Ca1—O1—Ca1^ii	15.27 (18)
O1—C1—Ca1—C1^i	−69.13 (14)	N1^i—Ca1—O1—Ca1^ii	68.93 (8)
O2—C1—Ca1—Ca1^ii	−153.94 (18)	C1^i—Ca1—O1—Ca1^ii	−100.51 (8)
O1—C1—Ca1—Ca1^ii	23.73 (12)	C1—Ca1—O1—Ca1^ii	142.91 (18)
O2—C1—Ca1—Ca1^iv	54.73 (17)	Ca1^iv—Ca1—O1—Ca1^ii	−156.78 (5)
O1—C1—Ca1—Ca1^iv	−127.61 (14)	O1—C1—O2—Ca1	−2.4 (3)
C14—C15—N1—C11	−1.9 (4)	C2—C1—O2—Ca1	175.4 (2)
C14—C15—N1—Ca1	176.9 (2)	O1^ii—Ca1—O2—C1	39.50 (18)
C12—C11—N1—C15	0.7 (3)	O1^iii—Ca1—O2—C1	−161.42 (18)
C11^i—C11—N1—C15	−178.8 (3)	O2^i—Ca1—O2—C1	−54.12 (15)
C12—C11—N1—Ca1	−178.07 (18)	O1—Ca1—O2—C1	1.31 (15)
C11^i—C11—N1—Ca1	2.4 (3)	O1^i—Ca1—O2—C1	−94.55 (17)
O1^ii—Ca1—N1—C15	−104.4 (2)	N1—Ca1—O2—C1	148.90 (15)
O1^iii—Ca1—N1—C15	87.4 (2)	N1^i—Ca1—O2—C1	111.13 (17)
O2^i—Ca1—N1—C15	−25.7 (2)	C1^i—Ca1—O2—C1	−77.1 (2)
O2—Ca1—N1—C15	137.96 (19)	Ca1^ii—Ca1—O2—C1	21.84 (16)
O1—Ca1—N1—C15	−118.6 (2)	Ca1^iv—Ca1—O2—C1	−127.05 (16)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2	0.93	2.58	2.886 (3)	100

Poly[(1,10-phenanthroline-κ²N,N')(µ-3-phenylprop-2-enoato-κ³O,O':O)(µ-3-phenylprop-2-enoato-κ⁴O:O,O':O')barium(I)] (Ba)

Crystal data

[Ba(C10H7O2)2(C10H8N2)]	Dx = 1.535 Mg m^−3
Mr = 611.84	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 9950 reflections
Hall symbol: -R 3	θ = 2.6–26.4°
a = 36.4542 (7) Å	µ = 1.54 mm^−1
c = 10.3535 (2) Å	T = 295 K
V = 11915.5 (6) Å^3	Prism, colorless
Z = 18	0.16 × 0.14 × 0.13 mm
F(000) = 5472

Data collection

Bruker APEXII diffractometer	7729 independent reflections
Radiation source: Enraf Nonius FR590	5619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
CCD rotation images, thick slices scans	θmax = 30.1°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −51→51
Tmin = 0.668, Tmax = 0.764	k = −45→51
66922 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0391P)^2 + 16.9728P] where P = (Fo^2 + 2Fc^2)/3
7729 reflections	(Δ/σ)max = 0.006
334 parameters	Δρmax = 1.98 e Å^−3
0 restraints	Δρmin = −0.55 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.37461 (9)	0.05822 (9)	1.3496 (3)	0.0332 (6)
C1B	0.42708 (9)	0.10078 (9)	0.8721 (3)	0.0361 (6)
C2A	0.42061 (11)	0.09183 (10)	1.3431 (3)	0.0473 (8)
H2A	0.433	0.1016	1.2626	0.057*
C2B	0.46905 (10)	0.12678 (10)	0.9366 (3)	0.0409 (7)
H2B	0.475	0.1157	1.0093	0.049*
C3A	0.44365 (11)	0.10765 (10)	1.4460 (3)	0.0472 (8)
H3A	0.4293	0.0993	1.5243	0.057*
C3B	0.49809 (10)	0.16460 (10)	0.8960 (3)	0.0441 (7)
H3B	0.4906	0.1757	0.8265	0.053*
C4A	0.48975 (11)	0.13723 (11)	1.4543 (4)	0.0558 (9)
C4B	0.54107 (10)	0.19127 (10)	0.9487 (3)	0.0440 (7)
C5A	0.51003 (13)	0.13953 (14)	1.5686 (5)	0.0729 (12)
H5A	0.494	0.1231	1.6379	0.088*
C5B	0.56149 (12)	0.17450 (12)	1.0195 (4)	0.0584 (10)
H5B	0.5476	0.1456	1.0366	0.07*
C6A	0.55259 (16)	0.16488 (18)	1.5842 (6)	0.0986 (18)
H6A	0.5655	0.1653	1.6622	0.118*
C6B	0.60215 (13)	0.20007 (14)	1.0650 (4)	0.0716 (12)
H6B	0.6156	0.1882	1.1106	0.086*
C7A	0.57595 (17)	0.1896 (2)	1.4837 (8)	0.125 (3)
H7A	0.6052	0.2065	1.4923	0.15*
C7B	0.62277 (13)	0.24273 (14)	1.0435 (5)	0.0732 (12)
H7B	0.6499	0.26	1.0762	0.088*
C8A	0.55688 (19)	0.1899 (2)	1.3701 (7)	0.127 (3)
H8A	0.5729	0.2079	1.3036	0.152*
C9B	0.60304 (13)	0.26010 (12)	0.9725 (5)	0.0709 (12)
H9B	0.617	0.2891	0.9572	0.085*
C10A	0.51308 (15)	0.16288 (16)	1.3537 (5)	0.0978 (18)
H10A	0.5001	0.1624	1.2759	0.117*
C10B	0.56295 (12)	0.23465 (11)	0.9247 (4)	0.0554 (9)
H10B	0.5502	0.2466	0.8756	0.066*
C11	0.46767 (10)	0.03124 (11)	0.8532 (3)	0.0439 (7)
H11	0.4458	0.0207	0.793	0.053*
C12	0.50933 (11)	0.05264 (12)	0.8076 (3)	0.0506 (8)
H12	0.5148	0.0561	0.7193	0.061*
C13	0.54152 (11)	0.06817 (11)	0.8933 (4)	0.0506 (8)
H13	0.5694	0.0822	0.8645	0.061*
C14	0.53275 (10)	0.06311 (10)	1.0260 (3)	0.0409 (7)
C15	0.56511 (11)	0.07948 (12)	1.1230 (4)	0.0526 (9)
H15	0.5934	0.0937	1.098	0.063*
C16	0.55558 (11)	0.07484 (12)	1.2474 (4)	0.0554 (9)
H16	0.5773	0.0867	1.308	0.066*
C17	0.51261 (10)	0.05196 (10)	1.2904 (3)	0.0428 (7)
C18	0.50107 (12)	0.04412 (13)	1.4216 (3)	0.0557 (9)
H18	0.5219	0.0552	1.4852	0.067*
C19	0.45939 (13)	0.02022 (13)	1.4559 (3)	0.0559 (9)
H19	0.4516	0.0146	1.5423	0.067*
C20	0.42900 (11)	0.00459 (11)	1.3587 (3)	0.0446 (8)
H20	0.4007	−0.0116	1.3828	0.054*
C21	0.47915 (9)	0.03451 (9)	1.1999 (3)	0.0344 (6)
C22	0.48975 (9)	0.04100 (9)	1.0638 (3)	0.0339 (6)
N1	0.45755 (7)	0.02511 (8)	0.9766 (2)	0.0351 (5)
N2	0.43772 (8)	0.01131 (8)	1.2350 (2)	0.0372 (6)
O1A	0.35922 (7)	0.03538 (7)	1.2511 (2)	0.0443 (5)
O1B	0.39982 (6)	0.06800 (6)	0.9313 (2)	0.0399 (5)
O2A	0.35425 (7)	0.05311 (7)	1.4510 (2)	0.0438 (5)
O2B	0.42084 (7)	0.11185 (7)	0.7640 (2)	0.0496 (6)
Ba1	0.368903 (5)	−0.007544 (5)	1.049353 (15)	0.02866 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0411 (16)	0.0282 (14)	0.0334 (15)	0.0196 (13)	0.0030 (12)	0.0032 (12)
C1B	0.0387 (16)	0.0299 (15)	0.0389 (17)	0.0166 (13)	−0.0008 (13)	0.0000 (12)
C2A	0.0506 (19)	0.0420 (18)	0.0426 (19)	0.0180 (16)	0.0094 (15)	−0.0072 (15)
C2B	0.0428 (17)	0.0385 (16)	0.0365 (17)	0.0165 (14)	−0.0047 (13)	0.0022 (13)
C3A	0.0469 (19)	0.0421 (18)	0.050 (2)	0.0204 (16)	0.0070 (15)	−0.0040 (15)
C3B	0.0414 (17)	0.0397 (17)	0.0487 (19)	0.0184 (15)	−0.0035 (14)	0.0036 (14)
C4A	0.0436 (19)	0.0442 (19)	0.069 (3)	0.0140 (16)	0.0059 (18)	−0.0175 (18)
C4B	0.0401 (17)	0.0392 (17)	0.0458 (19)	0.0147 (14)	0.0011 (14)	−0.0039 (14)
C5A	0.051 (2)	0.073 (3)	0.078 (3)	0.019 (2)	−0.005 (2)	−0.019 (2)
C5B	0.052 (2)	0.0428 (19)	0.071 (3)	0.0168 (17)	−0.0123 (19)	0.0008 (18)
C6A	0.055 (3)	0.114 (4)	0.099 (4)	0.021 (3)	−0.009 (3)	−0.035 (3)
C6B	0.050 (2)	0.076 (3)	0.079 (3)	0.024 (2)	−0.014 (2)	0.005 (2)
C7A	0.048 (3)	0.142 (6)	0.133 (6)	0.009 (3)	0.002 (3)	−0.071 (5)
C7B	0.043 (2)	0.065 (3)	0.085 (3)	0.007 (2)	−0.009 (2)	−0.013 (2)
C8A	0.077 (4)	0.126 (5)	0.099 (5)	−0.008 (3)	0.036 (3)	−0.024 (4)
C9B	0.048 (2)	0.040 (2)	0.102 (3)	0.0049 (18)	0.008 (2)	−0.010 (2)
C10A	0.063 (3)	0.095 (4)	0.077 (3)	−0.003 (3)	0.009 (2)	−0.022 (3)
C10B	0.050 (2)	0.0376 (18)	0.074 (3)	0.0184 (16)	0.0056 (18)	0.0018 (17)
C11	0.0433 (18)	0.062 (2)	0.0325 (16)	0.0306 (17)	−0.0021 (13)	−0.0016 (14)
C12	0.051 (2)	0.066 (2)	0.0402 (19)	0.0328 (18)	0.0099 (16)	0.0019 (16)
C13	0.0384 (18)	0.056 (2)	0.060 (2)	0.0258 (16)	0.0090 (16)	0.0018 (17)
C14	0.0363 (16)	0.0445 (17)	0.0489 (19)	0.0255 (14)	0.0023 (14)	−0.0005 (14)
C15	0.0314 (17)	0.060 (2)	0.065 (2)	0.0213 (16)	−0.0060 (16)	−0.0061 (18)
C16	0.0380 (18)	0.067 (2)	0.060 (2)	0.0254 (17)	−0.0181 (16)	−0.0142 (19)
C17	0.0440 (18)	0.0485 (18)	0.0441 (18)	0.0293 (15)	−0.0136 (14)	−0.0103 (14)
C18	0.062 (2)	0.073 (3)	0.041 (2)	0.040 (2)	−0.0215 (17)	−0.0121 (18)
C19	0.069 (3)	0.075 (3)	0.0335 (18)	0.044 (2)	−0.0061 (17)	−0.0010 (17)
C20	0.0479 (19)	0.056 (2)	0.0361 (17)	0.0304 (16)	−0.0003 (14)	0.0029 (15)
C21	0.0365 (15)	0.0364 (15)	0.0366 (16)	0.0230 (13)	−0.0084 (12)	−0.0050 (12)
C22	0.0352 (15)	0.0351 (15)	0.0382 (16)	0.0226 (13)	−0.0049 (12)	−0.0033 (12)
N1	0.0337 (13)	0.0442 (14)	0.0322 (13)	0.0229 (11)	−0.0012 (10)	−0.0003 (11)
N2	0.0368 (14)	0.0460 (15)	0.0323 (13)	0.0234 (12)	−0.0050 (10)	−0.0015 (11)
O1A	0.0504 (13)	0.0427 (12)	0.0346 (12)	0.0194 (11)	0.0036 (10)	−0.0057 (9)
O1B	0.0371 (11)	0.0330 (11)	0.0437 (12)	0.0132 (9)	0.0011 (9)	0.0068 (9)
O2A	0.0509 (13)	0.0445 (12)	0.0306 (11)	0.0199 (11)	0.0088 (10)	0.0012 (9)
O2B	0.0450 (13)	0.0493 (13)	0.0406 (13)	0.0132 (11)	−0.0053 (10)	0.0118 (10)
Ba1	0.03078 (9)	0.03180 (10)	0.02337 (9)	0.01563 (7)	0.00041 (6)	0.00206 (6)

Geometric parameters (Å, º)

C1A—O2A	1.244 (3)	C11—H11	0.93
C1A—O1A	1.258 (3)	C12—C13	1.350 (5)
C1A—C2A	1.505 (4)	C12—H12	0.93
C1A—Ba1^i	3.279 (3)	C13—C14	1.402 (5)
C1B—O2B	1.249 (4)	C13—H13	0.93
C1B—O1B	1.266 (3)	C14—C22	1.413 (4)
C1B—C2B	1.495 (4)	C14—C15	1.433 (5)
C1B—Ba1^ii	3.209 (3)	C15—C16	1.322 (5)
C2A—C3A	1.300 (5)	C15—H15	0.93
C2A—H2A	0.93	C16—C17	1.429 (5)
C2B—C3B	1.318 (4)	C16—H16	0.93
C2B—H2B	0.93	C17—C18	1.408 (5)
C3A—C4A	1.477 (5)	C17—C21	1.413 (4)
C3A—H3A	0.93	C18—C19	1.367 (5)
C3B—C4B	1.475 (4)	C18—H18	0.93
C3B—H3B	0.93	C19—C20	1.391 (5)
C4A—C10A	1.374 (6)	C19—H19	0.93
C4A—C5A	1.375 (6)	C20—N2	1.313 (4)
C4B—C5B	1.386 (5)	C20—H20	0.93
C4B—C10B	1.392 (5)	C21—N2	1.361 (4)
C5A—C6A	1.361 (6)	C21—C22	1.449 (4)
C5A—H5A	0.93	C22—N1	1.359 (4)
C5B—C6B	1.381 (5)	Ba1—N1	2.929 (2)
C5B—H5B	0.93	Ba1—N2	2.956 (2)
C6A—C7A	1.361 (9)	O1A—Ba1	2.736 (2)
C6A—H6A	0.93	O1A—Ba1^i	2.893 (2)
C6B—C7B	1.365 (6)	O1B—Ba1	2.692 (2)
C6B—H6B	0.93	O1B—Ba1^ii	2.908 (2)
C7A—C8A	1.369 (9)	O2A—Ba1^iii	2.779 (2)
C7A—H7A	0.93	O2A—Ba1^i	2.976 (2)
C7B—C9B	1.383 (6)	O2B—Ba1^ii	2.778 (2)
C7B—H7B	0.93	Ba1—O1A^ii	2.893 (2)
C8A—C10A	1.405 (7)	Ba1—O1B^i	2.908 (2)
C8A—H8A	0.93	Ba1—O2A^iv	2.779 (2)
C9B—C10B	1.373 (5)	Ba1—O2A^ii	2.975 (2)
C9B—H9B	0.93	Ba1—O2B^i	2.778 (2)
C10A—H10A	0.93	Ba1—C1A^ii	3.279 (3)
C10B—H10B	0.93	Ba1—C1B^i	3.209 (3)
C11—N1	1.318 (4)	Ba1—Ba1^ii	4.2721 (2)
C11—C12	1.398 (5)
O2A—C1A—O1A	123.4 (3)	C19—C20—H20	118
O2A—C1A—C2A	119.9 (3)	N2—C21—C17	122.9 (3)
O1A—C1A—C2A	116.7 (3)	N2—C21—C22	118.9 (2)
O2A—C1A—Ba1^i	65.01 (16)	C17—C21—C22	118.2 (3)
O1A—C1A—Ba1^i	61.26 (15)	N1—C22—C14	122.3 (3)
C2A—C1A—Ba1^i	159.5 (2)	N1—C22—C21	118.2 (3)
O2B—C1B—O1B	123.7 (3)	C14—C22—C21	119.4 (3)
O2B—C1B—C2B	119.3 (3)	C11—N1—C22	117.6 (3)
O1B—C1B—C2B	117.0 (3)	C11—N1—Ba1	118.45 (19)
O2B—C1B—Ba1^ii	58.89 (15)	C22—N1—Ba1	123.01 (18)
O1B—C1B—Ba1^ii	64.90 (15)	C20—N2—C21	117.8 (3)
C2B—C1B—Ba1^ii	175.3 (2)	C20—N2—Ba1	119.5 (2)
C3A—C2A—C1A	122.3 (3)	C21—N2—Ba1	121.33 (18)
C3A—C2A—H2A	118.9	C1A—O1A—Ba1	148.8 (2)
C1A—C2A—H2A	118.9	C1A—O1A—Ba1^i	96.34 (17)
C3B—C2B—C1B	123.6 (3)	Ba1—O1A—Ba1^i	98.70 (6)
C3B—C2B—H2B	118.2	C1B—O1B—Ba1	156.17 (19)
C1B—C2B—H2B	118.2	C1B—O1B—Ba1^ii	91.89 (17)
C2A—C3A—C4A	128.2 (3)	Ba1—O1B—Ba1^ii	99.37 (6)
C2A—C3A—H3A	115.9	C1A—O2A—Ba1^iii	154.8 (2)
C4A—C3A—H3A	115.9	C1A—O2A—Ba1^i	92.71 (17)
C2B—C3B—C4B	127.2 (3)	Ba1^iii—O2A—Ba1^i	95.81 (6)
C2B—C3B—H3B	116.4	C1B—O2B—Ba1^ii	98.47 (18)
C4B—C3B—H3B	116.4	O1B—Ba1—O1A	82.49 (6)
C10A—C4A—C5A	118.7 (4)	O1B—Ba1—O2B^i	157.13 (6)
C10A—C4A—C3A	123.0 (4)	O1A—Ba1—O2B^i	118.04 (6)
C5A—C4A—C3A	118.4 (4)	O1B—Ba1—O2A^iv	71.95 (7)
C5B—C4B—C10B	117.8 (3)	O1A—Ba1—O2A^iv	147.88 (7)
C5B—C4B—C3B	122.2 (3)	O2B^i—Ba1—O2A^iv	91.27 (7)
C10B—C4B—C3B	120.0 (3)	O1B—Ba1—O1A^ii	73.92 (6)
C6A—C5A—C4A	122.6 (5)	O1A—Ba1—O1A^ii	90.240 (18)
C6A—C5A—H5A	118.7	O2B^i—Ba1—O1A^ii	113.42 (7)
C4A—C5A—H5A	118.7	O2A^iv—Ba1—O1A^ii	64.53 (6)
C6B—C5B—C4B	121.0 (4)	O1B—Ba1—O1B^i	155.46 (7)
C6B—C5B—H5B	119.5	O1A—Ba1—O1B^i	73.03 (6)
C4B—C5B—H5B	119.5	O2B^i—Ba1—O1B^i	45.83 (6)
C7A—C6A—C5A	118.8 (6)	O2A^iv—Ba1—O1B^i	131.45 (6)
C7A—C6A—H6A	120.6	O1A^ii—Ba1—O1B^i	107.26 (6)
C5A—C6A—H6A	120.6	O1B—Ba1—N1	69.82 (6)
C7B—C6B—C5B	120.5 (4)	O1A—Ba1—N1	113.29 (7)
C7B—C6B—H6B	119.8	O2B^i—Ba1—N1	91.50 (7)
C5B—C6B—H6B	119.8	O2A^iv—Ba1—N1	76.15 (6)
C6A—C7A—C8A	120.7 (5)	O1A^ii—Ba1—N1	132.85 (6)
C6A—C7A—H7A	119.7	O1B^i—Ba1—N1	118.29 (6)
C8A—C7A—H7A	119.7	O1B—Ba1—N2	100.66 (7)
C6B—C7B—C9B	119.5 (4)	O1A—Ba1—N2	73.01 (7)
C6B—C7B—H7B	120.3	O2B^i—Ba1—N2	77.90 (7)
C9B—C7B—H7B	120.3	O2A^iv—Ba1—N2	129.86 (7)
C7A—C8A—C10A	120.1 (6)	O1A^ii—Ba1—N2	163.05 (7)
C7A—C8A—H8A	119.9	O1B^i—Ba1—N2	70.89 (7)
C10A—C8A—H8A	119.9	N1—Ba1—N2	55.74 (7)
C10B—C9B—C7B	120.2 (4)	O1B—Ba1—O2A^ii	104.64 (6)
C10B—C9B—H9B	119.9	O1A—Ba1—O2A^ii	63.90 (6)
C7B—C9B—H9B	119.9	O2B^i—Ba1—O2A^ii	94.17 (7)
C4A—C10A—C8A	119.0 (5)	O2A^iv—Ba1—O2A^ii	103.62 (5)
C4A—C10A—H10A	120.5	O1A^ii—Ba1—O2A^ii	44.06 (6)
C8A—C10A—H10A	120.5	O1B^i—Ba1—O2A^ii	66.22 (6)
C9B—C10B—C4B	121.0 (4)	N1—Ba1—O2A^ii	174.33 (6)
C9B—C10B—H10B	119.5	N2—Ba1—O2A^ii	125.69 (6)
C4B—C10B—H10B	119.5	O1B—Ba1—C1B^i	174.52 (7)
N1—C11—C12	123.8 (3)	O1A—Ba1—C1B^i	95.98 (7)
N1—C11—H11	118.1	O2B^i—Ba1—C1B^i	22.64 (7)
C12—C11—H11	118.1	O2A^iv—Ba1—C1B^i	111.18 (7)
C13—C12—C11	119.1 (3)	O1A^ii—Ba1—C1B^i	111.41 (7)
C13—C12—H12	120.5	O1B^i—Ba1—C1B^i	23.22 (6)
C11—C12—H12	120.5	N1—Ba1—C1B^i	106.20 (7)
C12—C13—C14	119.7 (3)	N2—Ba1—C1B^i	73.86 (7)
C12—C13—H13	120.1	O2A^ii—Ba1—C1B^i	79.23 (7)
C14—C13—H13	120.1	O1B—Ba1—C1A^ii	86.61 (7)
C13—C14—C22	117.5 (3)	O1A—Ba1—C1A^ii	73.36 (7)
C13—C14—C15	123.1 (3)	O2B^i—Ba1—C1A^ii	108.06 (7)
C22—C14—C15	119.4 (3)	O2A^iv—Ba1—C1A^ii	85.76 (7)
C16—C15—C14	121.3 (3)	O1A^ii—Ba1—C1A^ii	22.41 (6)
C16—C15—H15	119.3	O1B^i—Ba1—C1A^ii	88.00 (6)
C14—C15—H15	119.3	N1—Ba1—C1A^ii	153.69 (7)
C15—C16—C17	121.3 (3)	N2—Ba1—C1A^ii	144.25 (7)
C15—C16—H16	119.3	O2A^ii—Ba1—C1A^ii	22.28 (6)
C17—C16—H16	119.3	C1B^i—Ba1—C1A^ii	98.03 (7)
C18—C17—C21	116.5 (3)	O1B—Ba1—Ba1^ii	42.19 (4)
C18—C17—C16	123.3 (3)	O1A—Ba1—Ba1^ii	104.02 (5)
C21—C17—C16	120.2 (3)	O2B^i—Ba1—Ba1^ii	131.02 (5)
C19—C18—C17	120.2 (3)	O2A^iv—Ba1—Ba1^ii	43.86 (5)
C19—C18—H18	119.9	O1A^ii—Ba1—Ba1^ii	39.28 (4)
C17—C18—H18	119.9	O1B^i—Ba1—Ba1^ii	146.35 (4)
C18—C19—C20	118.5 (3)	N1—Ba1—Ba1^ii	94.03 (5)
C18—C19—H19	120.7	N2—Ba1—Ba1^ii	141.58 (5)
C20—C19—H19	120.7	O2A^ii—Ba1—Ba1^ii	82.19 (4)
N2—C20—C19	124.1 (3)	C1B^i—Ba1—Ba1^ii	143.09 (5)
N2—C20—H20	118	C1A^ii—Ba1—Ba1^ii	59.91 (5)
O2A—C1A—C2A—C3A	20.4 (5)	Ba1^ii—O1B—Ba1—O1A	−120.62 (7)
O1A—C1A—C2A—C3A	−156.8 (3)	C1B—O1B—Ba1—O2B^i	−32.9 (6)
Ba1^i—C1A—C2A—C3A	−77.9 (7)	Ba1^ii—O1B—Ba1—O2B^i	84.22 (18)
O2B—C1B—C2B—C3B	11.0 (5)	C1B—O1B—Ba1—O2A^iv	−77.5 (5)
O1B—C1B—C2B—C3B	−169.9 (3)	Ba1^ii—O1B—Ba1—O2A^iv	39.68 (6)
C1A—C2A—C3A—C4A	173.1 (3)	C1B—O1B—Ba1—O1A^ii	−145.3 (5)
C1B—C2B—C3B—C4B	−176.1 (3)	Ba1^ii—O1B—Ba1—O1A^ii	−28.19 (6)
C2A—C3A—C4A—C10A	21.6 (6)	C1B—O1B—Ba1—O1B^i	118.2 (4)
C2A—C3A—C4A—C5A	−159.3 (4)	Ba1^ii—O1B—Ba1—O1B^i	−124.62 (13)
C2B—C3B—C4B—C5B	22.1 (6)	C1B—O1B—Ba1—N1	4.0 (5)
C2B—C3B—C4B—C10B	−159.7 (4)	Ba1^ii—O1B—Ba1—N1	121.13 (8)
C10A—C4A—C5A—C6A	−2.8 (7)	C1B—O1B—Ba1—N2	51.2 (5)
C3A—C4A—C5A—C6A	178.0 (4)	Ba1^ii—O1B—Ba1—N2	168.33 (6)
C10B—C4B—C5B—C6B	0.2 (6)	C1B—O1B—Ba1—O2A^ii	−177.3 (5)
C3B—C4B—C5B—C6B	178.4 (4)	Ba1^ii—O1B—Ba1—O2A^ii	−60.16 (7)
C4A—C5A—C6A—C7A	1.3 (8)	C1B—O1B—Ba1—C1A^ii	−164.1 (5)
C4B—C5B—C6B—C7B	1.5 (7)	Ba1^ii—O1B—Ba1—C1A^ii	−46.97 (7)
C5A—C6A—C7A—C8A	1.8 (10)	C1B—O1B—Ba1—Ba1^ii	−117.1 (5)
C5B—C6B—C7B—C9B	−1.7 (7)	C1A—O1A—Ba1—O1B	−88.1 (4)
C6A—C7A—C8A—C10A	−3.3 (11)	Ba1^i—O1A—Ba1—O1B	153.97 (8)
C6B—C7B—C9B—C10B	0.3 (7)	C1A—O1A—Ba1—O2B^i	81.2 (4)
C5A—C4A—C10A—C8A	1.3 (8)	Ba1^i—O1A—Ba1—O2B^i	−36.69 (10)
C3A—C4A—C10A—C8A	−179.6 (5)	C1A—O1A—Ba1—O2A^iv	−125.2 (3)
C7A—C8A—C10A—C4A	1.7 (10)	Ba1^i—O1A—Ba1—O2A^iv	116.88 (11)
C7B—C9B—C10B—C4B	1.4 (6)	C1A—O1A—Ba1—O1A^ii	−161.9 (4)
C5B—C4B—C10B—C9B	−1.6 (6)	Ba1^i—O1A—Ba1—O1A^ii	80.22 (5)
C3B—C4B—C10B—C9B	−179.9 (3)	C1A—O1A—Ba1—O1B^i	90.2 (4)
N1—C11—C12—C13	0.0 (5)	Ba1^i—O1A—Ba1—O1B^i	−27.77 (6)
C11—C12—C13—C14	−0.8 (5)	C1A—O1A—Ba1—N1	−23.9 (4)
C12—C13—C14—C22	0.9 (5)	Ba1^i—O1A—Ba1—N1	−141.85 (6)
C12—C13—C14—C15	−178.6 (3)	C1A—O1A—Ba1—N2	15.5 (4)
C13—C14—C15—C16	178.6 (4)	Ba1^i—O1A—Ba1—N2	−102.42 (8)
C22—C14—C15—C16	−1.0 (5)	C1A—O1A—Ba1—O2A^ii	161.5 (4)
C14—C15—C16—C17	2.3 (6)	Ba1^i—O1A—Ba1—O2A^ii	43.57 (6)
C15—C16—C17—C18	176.2 (4)	C1A—O1A—Ba1—C1B^i	86.6 (4)
C15—C16—C17—C21	−1.4 (5)	Ba1^i—O1A—Ba1—C1B^i	−31.33 (8)
C21—C17—C18—C19	0.9 (5)	C1A—O1A—Ba1—C1A^ii	−176.8 (4)
C16—C17—C18—C19	−176.8 (4)	Ba1^i—O1A—Ba1—C1A^ii	65.28 (7)
C17—C18—C19—C20	−1.0 (6)	C1A—O1A—Ba1—Ba1^ii	−124.7 (4)
C18—C19—C20—N2	0.0 (6)	Ba1^i—O1A—Ba1—Ba1^ii	117.40 (5)
C18—C17—C21—N2	0.1 (4)	C11—N1—Ba1—O1B	−61.9 (2)
C16—C17—C21—N2	177.9 (3)	C22—N1—Ba1—O1B	106.4 (2)
C18—C17—C21—C22	−178.6 (3)	C11—N1—Ba1—O1A	−133.9 (2)
C16—C17—C21—C22	−0.8 (4)	C22—N1—Ba1—O1A	34.5 (2)
C13—C14—C22—N1	−0.3 (4)	C11—N1—Ba1—O2B^i	104.6 (2)
C15—C14—C22—N1	179.3 (3)	C22—N1—Ba1—O2B^i	−87.1 (2)
C13—C14—C22—C21	179.2 (3)	C11—N1—Ba1—O2A^iv	13.6 (2)
C15—C14—C22—C21	−1.2 (4)	C22—N1—Ba1—O2A^iv	−178.0 (2)
N2—C21—C22—N1	2.9 (4)	C11—N1—Ba1—O1A^ii	−20.0 (3)
C17—C21—C22—N1	−178.4 (3)	C22—N1—Ba1—O1A^ii	148.41 (19)
N2—C21—C22—C14	−176.7 (3)	C11—N1—Ba1—O1B^i	143.5 (2)
C17—C21—C22—C14	2.0 (4)	C22—N1—Ba1—O1B^i	−48.1 (2)
C12—C11—N1—C22	0.6 (5)	C11—N1—Ba1—N2	178.8 (3)
C12—C11—N1—Ba1	169.7 (3)	C22—N1—Ba1—N2	−12.8 (2)
C14—C22—N1—C11	−0.5 (4)	C11—N1—Ba1—C1B^i	122.0 (2)
C21—C22—N1—C11	−180.0 (3)	C22—N1—Ba1—C1B^i	−69.6 (2)
C14—C22—N1—Ba1	−169.0 (2)	C11—N1—Ba1—C1A^ii	−34.3 (3)
C21—C22—N1—Ba1	11.5 (3)	C22—N1—Ba1—C1A^ii	134.1 (2)
C19—C20—N2—C21	1.0 (5)	C11—N1—Ba1—Ba1^ii	−26.8 (2)
C19—C20—N2—Ba1	−166.1 (3)	C22—N1—Ba1—Ba1^ii	141.6 (2)
C17—C21—N2—C20	−1.0 (4)	C20—N2—Ba1—O1B	124.2 (2)
C22—C21—N2—C20	177.6 (3)	C21—N2—Ba1—O1B	−42.3 (2)
C17—C21—N2—Ba1	165.8 (2)	C20—N2—Ba1—O1A	45.6 (2)
C22—C21—N2—Ba1	−15.6 (3)	C21—N2—Ba1—O1A	−121.0 (2)
O2A—C1A—O1A—Ba1	−138.8 (3)	C20—N2—Ba1—O2B^i	−79.0 (2)
C2A—C1A—O1A—Ba1	38.4 (5)	C21—N2—Ba1—O2B^i	114.4 (2)
Ba1^i—C1A—O1A—Ba1	−118.5 (4)	C20—N2—Ba1—O2A^iv	−160.4 (2)
O2A—C1A—O1A—Ba1^i	−20.3 (3)	C21—N2—Ba1—O2A^iv	33.0 (2)
C2A—C1A—O1A—Ba1^i	156.9 (2)	C20—N2—Ba1—O1A^ii	54.7 (4)
O2B—C1B—O1B—Ba1	122.3 (4)	C21—N2—Ba1—O1A^ii	−111.9 (3)
C2B—C1B—O1B—Ba1	−56.7 (6)	C20—N2—Ba1—O1B^i	−31.9 (2)
Ba1^ii—C1B—O1B—Ba1	118.5 (5)	C21—N2—Ba1—O1B^i	161.5 (2)
O2B—C1B—O1B—Ba1^ii	3.8 (3)	C20—N2—Ba1—N1	−179.3 (3)
C2B—C1B—O1B—Ba1^ii	−175.3 (2)	C21—N2—Ba1—N1	14.09 (19)
O1A—C1A—O2A—Ba1^iii	129.4 (4)	C20—N2—Ba1—O2A^ii	7.4 (3)
C2A—C1A—O2A—Ba1^iii	−47.7 (6)	C21—N2—Ba1—O2A^ii	−159.21 (19)
Ba1^i—C1A—O2A—Ba1^iii	109.8 (4)	C20—N2—Ba1—C1B^i	−56.1 (2)
O1A—C1A—O2A—Ba1^i	19.6 (3)	C21—N2—Ba1—C1B^i	137.4 (2)
C2A—C1A—O2A—Ba1^i	−157.5 (2)	C20—N2—Ba1—C1A^ii	25.1 (3)
O1B—C1B—O2B—Ba1^ii	−4.0 (3)	C21—N2—Ba1—C1A^ii	−141.46 (19)
C2B—C1B—O2B—Ba1^ii	175.0 (2)	C20—N2—Ba1—Ba1^ii	136.9 (2)
C1B—O1B—Ba1—O1A	122.2 (5)	C21—N2—Ba1—Ba1^ii	−29.7 (2)

Symmetry codes: (i) −x+y+2/3, −x+1/3, z+1/3; (ii) −y+1/3, x−y−1/3, z−1/3; (iii) −y+1/3, x−y−1/3, z+2/3; (iv) −x+y+2/3, −x+1/3, z−2/3.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3A···O2A	0.93	2.51	2.846 (5)	102
C3A—H3A···O2B^v	0.93	2.57	3.418 (4)	152
C3B—H3B···O2B	0.93	2.53	2.843 (5)	100
C11—H11···O2A^iv	0.93	2.54	3.303 (5)	140
C13—H13···O2B^vi	0.93	2.60	3.379 (6)	142
C20—H20···O1B^i	0.93	2.54	3.248 (5)	133

Symmetry codes: (i) −x+y+2/3, −x+1/3, z+1/3; (iv) −x+y+2/3, −x+1/3, z−2/3; (v) x, y, z+1; (vi) x−y+1/3, x−1/3, −z+5/3.