Bis­(nitrato-κ2O,O′)(1,4,7,10,13-pentaoxa­cyclo­penta­decane)­calcium(II)

Brown, M.D.; Levason, W.; Webster, M.

doi:10.1107/S1600536805012973

metal-organic compounds

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ISSN: 2056-9890

Volume 61| Part 6| June 2005| Pages m1015-m1017

https://doi.org/10.1107/S1600536805012973

Bis(nitrato-κ²O,O′)(1,4,7,10,13-pentaoxacyclopentadecane)calcium(II)

Michael D. Brown,^a William Levason ^a and Michael Webster ^a ^*

^aSchool of Chemistry, University of Southampton, Southampton SO17 1BJ, England
^*Correspondence e-mail: m.webster@soton.ac.uk

(Received 29 March 2005; accepted 22 April 2005; online 7 May 2005)

The crystal structure of the title compound, [Ca(NO₃)₂(C₁₀H₂₀O₅)], at 120 K contains discrete molecules with nine-coordinate Ca atoms. There are two molecules in the asymmetric unit, related by a pseudo-inversion centre. The crown bonds through five O atoms [Ca—O = 2.464 (2)–2.567 (2) Å] and the nitrates are bidentate [Ca—O = 2.444 (2)–2.588 (2) Å]. The structure is a polymorph of a previously reported room-temperature form.

Comment

A room-temperature crystal structure of the title compound, (I), has been reported in the space group Pbca (No. 61) (Junk & Steed, 1999 ). There appears to be a typographical error in the cell dimensions reported in the paper (a and c have been interchanged) when compared with the values in the deposited CIF.

Our orthorhombic cell parameters were similar to the published values with, as expected, slightly smaller values due to the lower temperature (cell volume ca 2.7% smaller). However, the observed absences were not consistent with space group Pbca, but rather with space group Pca2₁ (No. 29) or Pbcm (No. 57) (both referred to standard settings). No solution emerged in the centrosymmetric space group Pbcm, but a solution did result from a direct methods calculation in Pca2₁, with two similar molecules in the asymmetric unit. The Flack (1983 ) parameter indicates an inversion twin.

There is a pseudo-centre of symmetry relating the two molecules and the solution in the space group Pbca was explored, even though well over half of the reflections were `observed' in the h0l zone with l odd (in the appropriate orientation). Although a solution with one molecule in the asymmetric unit could be obtained, refinement failed to reduce R1 below 0.18 and the displacement ellipsoids were very elongated.

The conclusion is that, at 120 K, the crystal structure is correctly described in the non-centrosymmetric space group Pca2₁ and represents a polymorph of the room-temperature structure.

On transforming the data to the Pbca orientation, the systematic absences correspond to the non-standard space group setting Pb2₁a (No. 29), which is a maximal non-isomorphic subgroup of Pbca. Whether this polymorph is stable at room temperature or a structural change occurs on cooling is not clear; however, the relationship between the two structures perhaps favours the latter.

The geometry agrees well with the earlier room-temperature structure (Junk & Steed, 1999). The Ca atoms are nine-coordinate with two bidentate nitrate groups (Fig. 1 and Table 1). The Ca—O bonds to the crown ligands [2.464 (2)–2.567 (2) Å] can be compared with the literature values [2.474 (3)–2.581 (4) Å; Junk & Steed, 1999]. The nitrates are bonded fairly symmetrically [differences in Ca—O within each ligand range from 0.006 (3) to 0.144 (3) Å] and, as noted before (Valle et al., 1986 ), the terminal N—O bond is shorter than the bridging bonds by ca 0.04 Å; values for one typical ligand are included in Table 1. There is also a distortion of the angles at nitrogen, the O—N—O angle involved in the four-membered ring being several degrees smaller than the ideal value of 120°.

Figure 1
One of the two molecules in the asymmetric unit of [Ca(NO₃)₂(15-crown-5)], showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. The other molecule is very similar.

Experimental

Crystals were isolated during the attempted crystal growth of a calcium azide/15-crown-5 complex. The nitrate was present in the mixture in small amounts from the synthesis [Ca(NO₃)₂(15-crown-5) and CsN₃ in methanol] and led to the isolated product.

Crystal data

[Ca(NO₃)₂(C₁₀H₂₀O₅)]
M_r = 384.36
Orthorhombic, Pca2₁
a = 15.1940 (15) Å
b = 15.908 (3) Å
c = 13.227 (2) Å
V = 3197.1 (8) Å³
Z = 8
D_x = 1.597 Mg m⁻³
Mo Kα radiation
Cell parameters from 3946 reflections
θ = 2.9–27.5°
μ = 0.45 mm⁻¹
T = 120 (2) K
Plate, colourless
0.22 × 0.17 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.814, T_max = 0.986
24234 measured reflections
6509 independent reflections
5672 reflections with I > 2σ(I)
R_int = 0.059
θ_max = 27.5°
h = −18 → 19
k = −20 → 18
l = −17 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.089
S = 1.03
6509 reflections
435 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0324P)² + 0.774P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983), 2675 Friedel pairs
Flack parameter = 0.48 (3)

Table 1
Selected geometric parameters (Å, °)

Ca1—O1	2.514 (2)
Ca1—O2	2.561 (2)
Ca1—O3	2.4759 (19)
Ca1—O4	2.476 (2)
Ca1—O5	2.523 (2)
Ca1—O11	2.454 (2)
Ca1—O12	2.460 (2)
Ca1—O14	2.588 (2)
Ca1—O15	2.444 (2)
Ca2—O6	2.539 (2)
Ca2—O7	2.567 (2)
Ca2—O8	2.464 (2)
Ca2—O9	2.502 (2)
Ca2—O10	2.514 (2)
Ca2—O17	2.453 (2)
Ca2—O18	2.502 (2)
Ca2—O20	2.448 (2)
Ca2—O21	2.548 (2)
N1—O11	1.268 (3)
N1—O12	1.263 (3)
N1—O13	1.226 (3)

O4—Ca1—O3	66.82 (6)
O4—Ca1—O5	66.15 (6)
O1—Ca1—O5	64.39 (7)
O3—Ca1—O2	65.25 (6)
O1—Ca1—O2	64.45 (7)
O11—Ca1—O12	52.36 (7)
O15—Ca1—O14	50.61 (7)
O8—Ca2—O9	66.28 (6)
O9—Ca2—O10	65.58 (6)
O10—Ca2—O6	64.58 (7)
O8—Ca2—O7	64.85 (7)
O6—Ca2—O7	64.10 (7)
O17—Ca2—O18	51.94 (7)
O20—Ca2—O21	50.99 (7)
O13—N1—O12	121.1 (3)
O13—N1—O11	121.1 (3)
O12—N1—O11	117.8 (2)

H atoms were placed in calculated positions (C—H = 0.99 Å) with a common refined U_iso.

Data collection: COLLECT (Hooft, 1998 ) and DENZO (Otwinowski & Minor, 1997 ); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536805012973/cf6421sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536805012973/cf6421Isup2.hkl

Computing details top

Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Bis(nitrato-κ²O,O')(1,4,7,10,13-pentaoxacyclopentadecane)calcium(II) top

Crystal data top

[Ca(NO₃)₂(C₁₀H₂₀O₅)]	F(000) = 1616
M_r = 384.36	D_x = 1.597 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3946 reflections
a = 15.1940 (15) Å	θ = 2.9–27.5°
b = 15.908 (3) Å	µ = 0.45 mm⁻¹
c = 13.227 (2) Å	T = 120 K
V = 3197.1 (8) Å³	Plate, colourless
Z = 8	0.22 × 0.17 × 0.03 mm

Data collection top

Nonius KappaCCD diffractometer	6509 independent reflections
Radiation source: Nonius rotating anode	5672 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.059
φ and ω scans	θ_max = 27.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −18→19
T_min = 0.814, T_max = 0.986	k = −20→18
24234 measured reflections	l = −17→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0324P)² + 0.774P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6509 reflections	Δρ_max = 0.26 e Å⁻³
435 parameters	Δρ_min = −0.33 e Å⁻³
3 restraints	Absolute structure: Flack (1983), 2675 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.48 (3)

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.

H atoms were placed in calculated positions with a common refined isotropic adp. Two SHELXL DELU commands were used to constrain N2—O16 and N3—O18 adp components.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ca1	0.05736 (3)	0.57918 (4)	0.63467 (4)	0.01992 (13)
Ca2	0.07350 (3)	0.06744 (4)	0.68675 (4)	0.02071 (13)
O1	0.06629 (12)	0.66896 (13)	0.79072 (16)	0.0244 (5)
O2	−0.03808 (12)	0.71183 (12)	0.63316 (17)	0.0264 (4)
O3	−0.10165 (12)	0.55365 (12)	0.60764 (16)	0.0246 (5)
O4	0.00142 (11)	0.45523 (14)	0.72796 (15)	0.0239 (5)
O5	0.16019 (12)	0.52707 (13)	0.77065 (15)	0.0246 (4)
O6	0.08852 (12)	0.15369 (13)	0.52612 (16)	0.0258 (5)
O7	−0.00591 (12)	0.20987 (13)	0.68624 (17)	0.0297 (5)
O8	−0.08743 (12)	0.06023 (13)	0.70818 (18)	0.0286 (5)
O9	0.00423 (11)	−0.05636 (13)	0.60148 (15)	0.0229 (4)
O10	0.16604 (12)	0.00232 (13)	0.55007 (16)	0.0248 (4)
C1	0.0368 (2)	0.75372 (19)	0.7780 (2)	0.0297 (7)
H1A	0.0781	0.7853	0.7343	0.0332 (13)*
H1B	0.0332	0.7824	0.8443	0.0332 (13)*
C2	−0.0519 (2)	0.7492 (2)	0.7301 (2)	0.0308 (7)
H2A	−0.0922	0.7143	0.7714	0.0332 (13)*
H2B	−0.0775	0.8061	0.7230	0.0332 (13)*
C3	−0.1181 (2)	0.6982 (2)	0.5775 (3)	0.0355 (8)
H3A	−0.1044	0.6922	0.5047	0.0332 (13)*
H3B	−0.1574	0.7474	0.5857	0.0332 (13)*
C4	−0.16399 (18)	0.6209 (2)	0.6141 (3)	0.0322 (8)
H4A	−0.1839	0.6284	0.6848	0.0332 (13)*
H4B	−0.2160	0.6087	0.5714	0.0332 (13)*
C5	−0.13424 (17)	0.47439 (18)	0.6444 (3)	0.0253 (6)
H5A	−0.1206	0.4295	0.5950	0.0332 (13)*
H5B	−0.1990	0.4773	0.6524	0.0332 (13)*
C6	−0.09226 (17)	0.4543 (2)	0.7442 (2)	0.0248 (7)
H6A	−0.1090	0.4968	0.7954	0.0332 (13)*
H6B	−0.1115	0.3983	0.7682	0.0332 (13)*
C7	0.05164 (19)	0.4206 (2)	0.8107 (2)	0.0270 (7)
H7A	0.0415	0.3593	0.8162	0.0332 (13)*
H7B	0.0344	0.4474	0.8753	0.0332 (13)*
C8	0.14598 (19)	0.4382 (2)	0.7877 (2)	0.0267 (7)
H8A	0.1830	0.4191	0.8449	0.0332 (13)*
H8B	0.1638	0.4063	0.7268	0.0332 (13)*
C9	0.16558 (19)	0.5742 (2)	0.8640 (2)	0.0296 (7)
H9A	0.2242	0.5667	0.8954	0.0332 (13)*
H9B	0.1202	0.5546	0.9122	0.0332 (13)*
C10	0.15087 (19)	0.6645 (2)	0.8381 (2)	0.0313 (7)
H10A	0.1520	0.6995	0.9000	0.0332 (13)*
H10B	0.1972	0.6847	0.7915	0.0332 (13)*
C11	0.0744 (2)	0.2423 (2)	0.5396 (3)	0.0326 (7)
H11A	0.0740	0.2712	0.4733	0.0332 (13)*
H11B	0.1219	0.2668	0.5815	0.0332 (13)*
C12	−0.0122 (2)	0.2524 (2)	0.5906 (3)	0.0339 (7)
H12A	−0.0254	0.3127	0.6010	0.0332 (13)*
H12B	−0.0596	0.2274	0.5490	0.0332 (13)*
C13	−0.0875 (2)	0.2044 (2)	0.7390 (3)	0.0401 (9)
H13A	−0.1204	0.2577	0.7303	0.0332 (13)*
H13B	−0.0759	0.1968	0.8120	0.0332 (13)*
C14	−0.14260 (19)	0.1328 (2)	0.7013 (3)	0.0353 (8)
H14A	−0.1958	0.1258	0.7437	0.0332 (13)*
H14B	−0.1611	0.1426	0.6305	0.0332 (13)*
C15	−0.12943 (17)	−0.01721 (18)	0.6792 (3)	0.0264 (6)
H15A	−0.1931	−0.0075	0.6684	0.0332 (13)*
H15B	−0.1226	−0.0593	0.7337	0.0332 (13)*
C16	−0.08866 (18)	−0.0496 (2)	0.5839 (2)	0.0248 (6)
H16A	−0.1135	−0.1052	0.5665	0.0332 (13)*
H16B	−0.1004	−0.0105	0.5273	0.0332 (13)*
C17	0.04986 (19)	−0.0988 (2)	0.5207 (2)	0.0275 (7)
H17A	0.0327	−0.0748	0.4545	0.0332 (13)*
H17B	0.0355	−0.1595	0.5209	0.0332 (13)*
C18	0.14651 (19)	−0.0858 (2)	0.5393 (2)	0.0278 (7)
H18A	0.1642	−0.1160	0.6016	0.0332 (13)*
H18B	0.1806	−0.1093	0.4821	0.0332 (13)*
C19	0.1708 (2)	0.0438 (2)	0.4544 (2)	0.0307 (7)
H19A	0.1203	0.0272	0.4115	0.0332 (13)*
H19B	0.2259	0.0281	0.4191	0.0332 (13)*
C20	0.16898 (19)	0.1361 (2)	0.4732 (2)	0.0311 (7)
H20A	0.2203	0.1532	0.5145	0.0332 (13)*
H20B	0.1708	0.1672	0.4084	0.0332 (13)*
N1	0.15064 (15)	0.69136 (16)	0.50441 (19)	0.0256 (6)
N2	0.12184 (16)	0.45287 (16)	0.49052 (19)	0.0245 (5)
N3	0.17255 (16)	0.19009 (16)	0.7974 (2)	0.0286 (6)
N4	0.12030 (15)	−0.05703 (16)	0.83964 (19)	0.0236 (5)
O11	0.17180 (14)	0.68333 (15)	0.59664 (17)	0.0336 (5)
O12	0.08380 (13)	0.65180 (14)	0.47334 (16)	0.0291 (5)
O13	0.19341 (14)	0.73635 (15)	0.44738 (18)	0.0380 (6)
O14	0.03969 (13)	0.46190 (14)	0.50064 (18)	0.0309 (5)
O15	0.17028 (13)	0.49595 (15)	0.54919 (18)	0.0338 (5)
O16	0.15427 (14)	0.40636 (14)	0.42598 (17)	0.0318 (5)
O17	0.19799 (13)	0.16340 (14)	0.71155 (16)	0.0309 (5)
O18	0.11277 (14)	0.14898 (14)	0.84208 (17)	0.0317 (5)
O19	0.20596 (14)	0.25334 (14)	0.83513 (18)	0.0390 (6)
O20	0.17272 (13)	−0.03119 (15)	0.77149 (16)	0.0297 (5)
O21	0.04135 (13)	−0.03286 (14)	0.83236 (17)	0.0277 (5)
O22	0.14603 (14)	−0.10248 (15)	0.90865 (17)	0.0327 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.0196 (2)	0.0212 (3)	0.0190 (3)	−0.0011 (2)	−0.0005 (2)	0.0005 (2)
Ca2	0.0211 (3)	0.0220 (3)	0.0190 (3)	−0.0021 (2)	0.0007 (2)	−0.0015 (3)
O1	0.0248 (10)	0.0232 (12)	0.0253 (11)	−0.0018 (8)	−0.0037 (8)	−0.0003 (9)
O2	0.0281 (10)	0.0234 (11)	0.0277 (11)	−0.0023 (8)	−0.0035 (9)	−0.0042 (10)
O3	0.0194 (9)	0.0187 (10)	0.0357 (13)	0.0038 (8)	0.0001 (8)	0.0039 (9)
O4	0.0182 (10)	0.0299 (12)	0.0236 (11)	−0.0006 (8)	−0.0009 (8)	0.0042 (9)
O5	0.0253 (10)	0.0283 (12)	0.0201 (11)	0.0004 (9)	−0.0015 (8)	0.0003 (9)
O6	0.0280 (10)	0.0235 (11)	0.0260 (11)	−0.0048 (8)	0.0052 (9)	0.0038 (9)
O7	0.0359 (11)	0.0209 (10)	0.0323 (11)	−0.0011 (8)	0.0050 (10)	0.0031 (10)
O8	0.0213 (10)	0.0183 (11)	0.0463 (15)	0.0025 (8)	−0.0036 (9)	−0.0054 (10)
O9	0.0196 (10)	0.0289 (12)	0.0202 (11)	−0.0003 (8)	0.0007 (7)	−0.0049 (8)
O10	0.0246 (10)	0.0286 (12)	0.0211 (11)	−0.0008 (8)	0.0010 (8)	−0.0004 (9)
C1	0.0438 (18)	0.0194 (17)	0.0260 (16)	−0.0060 (13)	0.0026 (13)	−0.0038 (13)
C2	0.0380 (16)	0.0220 (17)	0.0324 (17)	0.0051 (14)	0.0009 (13)	−0.0015 (14)
C3	0.0339 (17)	0.0226 (17)	0.050 (2)	0.0046 (13)	−0.0173 (15)	0.0024 (15)
C4	0.0192 (13)	0.0258 (17)	0.052 (2)	0.0060 (11)	−0.0049 (13)	−0.0050 (15)
C5	0.0207 (13)	0.0198 (15)	0.0355 (17)	−0.0019 (11)	−0.0005 (13)	0.0051 (14)
C6	0.0179 (13)	0.0263 (17)	0.0302 (17)	−0.0023 (11)	0.0070 (12)	−0.0005 (13)
C7	0.0294 (16)	0.0264 (17)	0.0254 (17)	−0.0001 (12)	−0.0037 (12)	0.0090 (13)
C8	0.0285 (16)	0.0277 (18)	0.0237 (16)	0.0053 (12)	−0.0007 (12)	0.0043 (13)
C9	0.0270 (15)	0.043 (2)	0.0189 (15)	−0.0020 (13)	−0.0039 (12)	−0.0025 (14)
C10	0.0266 (15)	0.040 (2)	0.0273 (17)	−0.0067 (13)	−0.0065 (12)	−0.0044 (14)
C11	0.0465 (18)	0.0229 (17)	0.0283 (17)	−0.0073 (14)	0.0010 (14)	0.0054 (13)
C12	0.0431 (18)	0.0237 (18)	0.0349 (18)	0.0038 (14)	−0.0035 (14)	0.0050 (14)
C13	0.0427 (19)	0.0243 (18)	0.053 (2)	0.0030 (14)	0.0160 (16)	−0.0033 (16)
C14	0.0256 (15)	0.0272 (18)	0.053 (2)	0.0078 (12)	0.0064 (14)	0.0039 (16)
C15	0.0194 (13)	0.0208 (15)	0.0389 (18)	−0.0034 (11)	0.0002 (13)	−0.0004 (14)
C16	0.0205 (14)	0.0280 (17)	0.0260 (16)	−0.0049 (12)	−0.0036 (12)	0.0005 (13)
C17	0.0302 (15)	0.0279 (17)	0.0242 (16)	−0.0008 (13)	0.0043 (12)	−0.0074 (13)
C18	0.0295 (15)	0.0299 (18)	0.0241 (16)	0.0028 (13)	0.0026 (12)	−0.0049 (14)
C19	0.0240 (14)	0.046 (2)	0.0217 (16)	−0.0013 (13)	0.0056 (12)	−0.0005 (14)
C20	0.0270 (15)	0.041 (2)	0.0254 (16)	−0.0085 (13)	0.0059 (12)	0.0060 (14)
N1	0.0291 (13)	0.0195 (14)	0.0281 (14)	0.0015 (10)	0.0089 (11)	−0.0028 (11)
N2	0.0268 (13)	0.0229 (14)	0.0237 (14)	0.0013 (10)	0.0002 (10)	0.0060 (9)
N3	0.0311 (13)	0.0240 (15)	0.0306 (15)	0.0031 (11)	−0.0116 (11)	0.0004 (11)
N4	0.0230 (12)	0.0264 (14)	0.0213 (13)	−0.0023 (10)	−0.0019 (10)	−0.0060 (11)
O11	0.0340 (11)	0.0390 (14)	0.0276 (12)	−0.0093 (10)	0.0007 (9)	−0.0018 (10)
O12	0.0336 (11)	0.0302 (12)	0.0237 (11)	−0.0035 (9)	−0.0014 (9)	0.0012 (9)
O13	0.0384 (12)	0.0325 (13)	0.0430 (14)	0.0014 (10)	0.0198 (10)	0.0127 (11)
O14	0.0259 (11)	0.0315 (13)	0.0352 (13)	0.0016 (9)	0.0025 (9)	0.0000 (10)
O15	0.0282 (11)	0.0428 (15)	0.0305 (13)	0.0034 (10)	−0.0058 (9)	−0.0058 (11)
O16	0.0381 (12)	0.0259 (12)	0.0314 (12)	0.0036 (9)	0.0071 (9)	0.0015 (9)
O17	0.0323 (11)	0.0341 (12)	0.0264 (12)	−0.0081 (9)	−0.0011 (8)	−0.0004 (9)
O18	0.0378 (12)	0.0311 (13)	0.0263 (11)	−0.0053 (10)	−0.0001 (9)	−0.0001 (10)
O19	0.0418 (12)	0.0237 (12)	0.0516 (15)	0.0003 (10)	−0.0188 (11)	−0.0093 (11)
O20	0.0270 (11)	0.0362 (13)	0.0257 (12)	0.0021 (9)	0.0016 (9)	0.0002 (10)
O21	0.0223 (10)	0.0319 (13)	0.0290 (12)	0.0002 (9)	−0.0007 (8)	0.0023 (10)
O22	0.0360 (12)	0.0310 (13)	0.0312 (13)	0.0009 (10)	−0.0095 (9)	0.0020 (10)

Geometric parameters (Å, º) top

Ca1—O1	2.514 (2)	C5—C6	1.501 (4)
Ca1—O2	2.561 (2)	C5—H5A	0.990
Ca1—O3	2.4759 (19)	C5—H5B	0.990
Ca1—O4	2.476 (2)	C6—H6A	0.990
Ca1—O5	2.523 (2)	C6—H6B	0.990
Ca1—O11	2.454 (2)	C7—C8	1.492 (4)
Ca1—O12	2.460 (2)	C7—H7A	0.990
Ca1—O14	2.588 (2)	C7—H7B	0.990
Ca1—O15	2.444 (2)	C8—H8A	0.990
Ca1—N1	2.857 (3)	C8—H8B	0.990
Ca1—N2	2.938 (3)	C9—C10	1.493 (5)
Ca2—O6	2.539 (2)	C9—H9A	0.990
Ca2—O7	2.567 (2)	C9—H9B	0.990
Ca2—O8	2.464 (2)	C10—H10A	0.990
Ca2—O9	2.502 (2)	C10—H10B	0.990
Ca2—O10	2.514 (2)	C11—C12	1.487 (4)
Ca2—O17	2.453 (2)	C11—H11A	0.990
Ca2—O18	2.502 (2)	C11—H11B	0.990
Ca2—O20	2.448 (2)	C12—H12A	0.990
Ca2—O21	2.548 (2)	C12—H12B	0.990
Ca2—N3	2.866 (3)	C13—C14	1.499 (5)
Ca2—N4	2.918 (3)	C13—H13A	0.990
O1—C1	1.430 (4)	C13—H13B	0.990
O1—C10	1.432 (3)	C14—H14A	0.990
O2—C2	1.429 (4)	C14—H14B	0.990
O2—C3	1.438 (3)	C15—C16	1.495 (4)
O3—C4	1.431 (3)	C15—H15A	0.990
O3—C5	1.439 (3)	C15—H15B	0.990
O4—C6	1.439 (3)	C16—H16A	0.990
O4—C7	1.444 (3)	C16—H16B	0.990
O5—C9	1.447 (4)	C17—C18	1.503 (4)
O5—C8	1.449 (4)	C17—H17A	0.990
O6—C20	1.436 (3)	C17—H17B	0.990
O6—C11	1.437 (4)	C18—H18A	0.990
O7—C13	1.425 (4)	C18—H18B	0.990
O7—C12	1.437 (4)	C19—C20	1.489 (5)
O8—C14	1.429 (3)	C19—H19A	0.990
O8—C15	1.439 (3)	C19—H19B	0.990
O9—C16	1.434 (3)	C20—H20A	0.990
O9—C17	1.441 (3)	C20—H20B	0.990
O10—C19	1.429 (4)	N1—O11	1.268 (3)
O10—C18	1.440 (4)	N1—O12	1.263 (3)
C1—C2	1.491 (4)	N1—O13	1.226 (3)
C1—H1A	0.990	N2—O16	1.232 (3)
C1—H1B	0.990	N2—O14	1.264 (3)
C2—H2A	0.990	N2—O15	1.270 (3)
C2—H2B	0.990	N3—O19	1.233 (3)
C3—C4	1.495 (5)	N3—O18	1.266 (3)
C3—H3A	0.990	N3—O17	1.272 (3)
C3—H3B	0.990	N4—O22	1.228 (3)
C4—H4A	0.990	N4—O21	1.263 (3)
C4—H4B	0.990	N4—O20	1.271 (3)

O15—Ca1—O11	76.91 (8)	O2—C2—C1	105.6 (2)
O15—Ca1—O12	74.84 (8)	O2—C2—H2A	110.6
O15—Ca1—O4	92.30 (8)	C1—C2—H2A	110.6
O11—Ca1—O4	152.00 (7)	O2—C2—H2B	110.6
O12—Ca1—O4	149.58 (7)	C1—C2—H2B	110.6
O15—Ca1—O3	121.96 (7)	H2A—C2—H2B	108.8
O11—Ca1—O3	140.59 (7)	O2—C3—C4	110.6 (2)
O12—Ca1—O3	96.38 (7)	O2—C3—H3A	109.5
O4—Ca1—O3	66.82 (6)	C4—C3—H3A	109.5
O15—Ca1—O1	130.52 (7)	O2—C3—H3B	109.5
O11—Ca1—O1	75.31 (7)	C4—C3—H3B	109.5
O12—Ca1—O1	115.89 (7)	H3A—C3—H3B	108.1
O4—Ca1—O1	93.55 (7)	O3—C4—C3	106.7 (2)
O3—Ca1—O1	105.34 (7)	O3—C4—H4A	110.4
O15—Ca1—O5	73.56 (7)	C3—C4—H4A	110.4
O11—Ca1—O5	85.94 (7)	O3—C4—H4B	110.4
O12—Ca1—O5	132.20 (7)	C3—C4—H4B	110.4
O4—Ca1—O5	66.15 (6)	H4A—C4—H4B	108.6
O3—Ca1—O5	130.81 (7)	O3—C5—C6	109.7 (2)
O1—Ca1—O5	64.39 (7)	O3—C5—H5A	109.7
O15—Ca1—O2	147.17 (8)	C6—C5—H5A	109.7
O11—Ca1—O2	80.98 (7)	O3—C5—H5B	109.7
O12—Ca1—O2	72.46 (7)	C6—C5—H5B	109.7
O4—Ca1—O2	117.76 (7)	H5A—C5—H5B	108.2
O3—Ca1—O2	65.25 (6)	O4—C6—C5	106.7 (2)
O1—Ca1—O2	64.45 (7)	O4—C6—H6A	110.4
O5—Ca1—O2	128.84 (7)	C5—C6—H6A	110.4
O11—Ca1—O12	52.36 (7)	O4—C6—H6B	110.4
O15—Ca1—O14	50.61 (7)	C5—C6—H6B	110.4
O11—Ca1—O14	114.82 (8)	H6A—C6—H6B	108.6
O12—Ca1—O14	76.18 (7)	O4—C7—C8	106.4 (2)
O4—Ca1—O14	74.44 (7)	O4—C7—H7A	110.5
O3—Ca1—O14	71.43 (7)	C8—C7—H7A	110.5
O1—Ca1—O14	167.92 (7)	O4—C7—H7B	110.5
O5—Ca1—O14	108.41 (7)	C8—C7—H7B	110.5
O2—Ca1—O14	122.01 (7)	H7A—C7—H7B	108.6
O15—Ca1—N1	73.21 (8)	O5—C8—C7	111.0 (2)
O11—Ca1—N1	26.24 (7)	O5—C8—H8A	109.4
O12—Ca1—N1	26.15 (7)	C7—C8—H8A	109.4
O4—Ca1—N1	165.49 (7)	O5—C8—H8B	109.4
O3—Ca1—N1	119.97 (7)	C7—C8—H8B	109.4
O1—Ca1—N1	96.51 (7)	H8A—C8—H8B	108.0
O5—Ca1—N1	109.14 (7)	O5—C9—C10	107.1 (2)
O2—Ca1—N1	76.20 (7)	O5—C9—H9A	110.3
O14—Ca1—N1	95.09 (7)	C10—C9—H9A	110.3
O15—Ca1—N2	25.22 (7)	O5—C9—H9B	110.3
O11—Ca1—N2	95.30 (7)	C10—C9—H9B	110.3
O12—Ca1—N2	72.77 (7)	H9A—C9—H9B	108.5
O4—Ca1—N2	83.87 (7)	O1—C10—C9	106.4 (2)
O3—Ca1—N2	96.87 (7)	O1—C10—H10A	110.4
O1—Ca1—N2	154.61 (7)	C9—C10—H10A	110.4
O5—Ca1—N2	91.80 (7)	O1—C10—H10B	110.4
O2—Ca1—N2	138.36 (7)	C9—C10—H10B	110.4
O14—Ca1—N2	25.44 (6)	H10A—C10—H10B	108.6
N1—Ca1—N2	82.55 (7)	O6—C11—C12	107.1 (2)
O20—Ca2—O17	82.11 (8)	O6—C11—H11A	110.3
O20—Ca2—O8	121.91 (7)	C12—C11—H11A	110.3
O17—Ca2—O8	141.15 (8)	O6—C11—H11B	110.3
O20—Ca2—O18	79.01 (8)	C12—C11—H11B	110.3
O8—Ca2—O18	99.57 (7)	H11A—C11—H11B	108.5
O20—Ca2—O9	87.76 (7)	O7—C12—C11	106.9 (2)
O17—Ca2—O9	151.01 (7)	O7—C12—H12A	110.3
O8—Ca2—O9	66.28 (6)	C11—C12—H12A	110.3
O18—Ca2—O9	151.49 (7)	O7—C12—H12B	110.3
O20—Ca2—O10	73.78 (7)	C11—C12—H12B	110.3
O17—Ca2—O10	85.49 (7)	H12A—C12—H12B	108.6
O8—Ca2—O10	128.21 (7)	O7—C13—C14	111.7 (3)
O18—Ca2—O10	132.13 (7)	O7—C13—H13A	109.3
O9—Ca2—O10	65.58 (6)	C14—C13—H13A	109.3
O20—Ca2—O6	132.39 (7)	O7—C13—H13B	109.3
O17—Ca2—O6	72.92 (7)	C14—C13—H13B	109.3
O8—Ca2—O6	102.15 (7)	H13A—C13—H13B	107.9
O18—Ca2—O6	112.67 (7)	O8—C14—C13	105.4 (2)
O9—Ca2—O6	94.93 (7)	O8—C14—H14A	110.7
O10—Ca2—O6	64.58 (7)	C13—C14—H14A	110.7
O17—Ca2—O21	115.88 (7)	O8—C14—H14B	110.7
O8—Ca2—O21	72.16 (7)	C13—C14—H14B	110.7
O18—Ca2—O21	75.51 (7)	H14A—C14—H14B	108.8
O9—Ca2—O21	76.54 (7)	O8—C15—C16	109.6 (2)
O10—Ca2—O21	113.13 (7)	O8—C15—H15A	109.7
O6—Ca2—O21	171.06 (7)	C16—C15—H15A	109.7
O20—Ca2—O7	148.93 (8)	O8—C15—H15B	109.7
O17—Ca2—O7	79.25 (7)	C16—C15—H15B	109.7
O8—Ca2—O7	64.85 (7)	H15A—C15—H15B	108.2
O18—Ca2—O7	69.92 (7)	O9—C16—C15	107.3 (2)
O9—Ca2—O7	119.73 (7)	O9—C16—H16A	110.3
O10—Ca2—O7	128.67 (7)	C15—C16—H16A	110.3
O6—Ca2—O7	64.10 (7)	O9—C16—H16B	110.3
O17—Ca2—O18	51.94 (7)	C15—C16—H16B	110.3
O20—Ca2—O21	50.99 (7)	H16A—C16—H16B	108.5
O21—Ca2—O7	117.68 (7)	O9—C17—C18	106.5 (2)
O20—Ca2—N3	83.06 (8)	O9—C17—H17A	110.4
O17—Ca2—N3	26.23 (7)	C18—C17—H17A	110.4
O8—Ca2—N3	119.61 (8)	O9—C17—H17B	110.4
O18—Ca2—N3	26.17 (7)	C18—C17—H17B	110.4
O9—Ca2—N3	170.79 (7)	H17A—C17—H17B	108.6
O10—Ca2—N3	110.74 (7)	O10—C18—C17	110.6 (2)
O6—Ca2—N3	90.69 (7)	O10—C18—H18A	109.5
O21—Ca2—N3	98.11 (8)	C17—C18—H18A	109.5
O7—Ca2—N3	69.34 (7)	O10—C18—H18B	109.5
O20—Ca2—N4	25.53 (7)	C17—C18—H18B	109.5
O17—Ca2—N4	98.15 (7)	H18A—C18—H18B	108.1
O8—Ca2—N4	97.50 (7)	O10—C19—C20	107.9 (2)
O18—Ca2—N4	74.02 (7)	O10—C19—H19A	110.1
O9—Ca2—N4	83.15 (7)	C20—C19—H19A	110.1
O10—Ca2—N4	94.73 (7)	O10—C19—H19B	110.1
O6—Ca2—N4	157.59 (7)	C20—C19—H19B	110.1
O21—Ca2—N4	25.59 (6)	H19A—C19—H19B	108.4
O7—Ca2—N4	135.66 (8)	O6—C20—C19	106.8 (2)
N3—Ca2—N4	88.87 (7)	O6—C20—H20A	110.4
C1—O1—C10	112.3 (2)	C19—C20—H20A	110.4
C1—O1—Ca1	114.99 (17)	O6—C20—H20B	110.4
C10—O1—Ca1	112.31 (17)	C19—C20—H20B	110.4
C2—O2—C3	113.5 (2)	H20A—C20—H20B	108.6
C2—O2—Ca1	114.75 (17)	O13—N1—O12	121.1 (3)
C3—O2—Ca1	111.03 (16)	O13—N1—O11	121.1 (3)
C4—O3—C5	114.0 (2)	O12—N1—O11	117.8 (2)
C4—O3—Ca1	120.98 (17)	O13—N1—Ca1	176.88 (19)
C5—O3—Ca1	115.52 (15)	O12—N1—Ca1	59.09 (14)
C6—O4—C7	114.0 (2)	O11—N1—Ca1	58.84 (14)
C6—O4—Ca1	114.94 (17)	O16—N2—O14	122.4 (3)
C7—O4—Ca1	120.02 (16)	O16—N2—O15	121.0 (2)
C9—O5—C8	112.4 (2)	O14—N2—O15	116.5 (3)
C9—O5—Ca1	118.23 (16)	O16—N2—Ca1	173.4 (2)
C8—O5—Ca1	109.86 (16)	O14—N2—Ca1	61.58 (15)
C20—O6—C11	112.3 (2)	O15—N2—Ca1	55.09 (14)
C20—O6—Ca2	112.27 (17)	O19—N3—O18	121.9 (3)
C11—O6—Ca2	114.39 (18)	O19—N3—O17	120.6 (3)
C13—O7—C12	113.7 (3)	O18—N3—O17	117.6 (2)
C13—O7—Ca2	110.72 (18)	O19—N3—Ca2	168.2 (2)
C12—O7—Ca2	116.67 (18)	O18—N3—Ca2	60.66 (14)
C14—O8—C15	114.5 (2)	O17—N3—Ca2	58.45 (13)
C14—O8—Ca2	122.48 (17)	O22—N4—O21	122.5 (2)
C15—O8—Ca2	116.68 (15)	O22—N4—O20	121.2 (2)
C16—O9—C17	112.9 (2)	O21—N4—O20	116.3 (2)
C16—O9—Ca2	115.32 (16)	O22—N4—Ca2	172.71 (19)
C17—O9—Ca2	120.03 (16)	O21—N4—Ca2	60.62 (14)
C19—O10—C18	111.9 (2)	O20—N4—Ca2	56.07 (14)
C19—O10—Ca2	118.35 (17)	N1—O11—Ca1	94.91 (16)
C18—O10—Ca2	110.91 (16)	N1—O12—Ca1	94.76 (17)
O1—C1—C2	106.7 (2)	N2—O14—Ca1	92.98 (17)
O1—C1—H1A	110.4	N2—O15—Ca1	99.68 (16)
C2—C1—H1A	110.4	N3—O17—Ca2	95.32 (16)
O1—C1—H1B	110.4	N3—O18—Ca2	93.17 (17)
C2—C1—H1B	110.4	N4—O20—Ca2	98.40 (16)
H1A—C1—H1B	108.6	N4—O21—Ca2	93.79 (16)

O15—Ca1—O1—C1	125.63 (19)	O20—Ca2—O9—C17	−74.1 (2)
O11—Ca1—O1—C1	67.77 (18)	O17—Ca2—O9—C17	−4.8 (3)
O12—Ca1—O1—C1	33.78 (19)	O8—Ca2—O9—C17	159.4 (2)
O4—Ca1—O1—C1	−138.30 (18)	O18—Ca2—O9—C17	−135.9 (2)
O3—Ca1—O1—C1	−71.37 (19)	O10—Ca2—O9—C17	−0.88 (19)
O5—Ca1—O1—C1	160.3 (2)	O6—Ca2—O9—C17	58.3 (2)
O2—Ca1—O1—C1	−19.12 (17)	O21—Ca2—O9—C17	−124.4 (2)
O14—Ca1—O1—C1	−144.1 (3)	O7—Ca2—O9—C17	121.2 (2)
N1—Ca1—O1—C1	52.18 (19)	O20—Ca2—O10—C19	−161.8 (2)
N2—Ca1—O1—C1	138.5 (2)	O17—Ca2—O10—C19	−78.76 (19)
O15—Ca1—O1—C10	−4.4 (2)	O8—Ca2—O10—C19	80.0 (2)
O11—Ca1—O1—C10	−62.28 (19)	O18—Ca2—O10—C19	−103.9 (2)
O12—Ca1—O1—C10	−96.28 (19)	O9—Ca2—O10—C19	103.15 (19)
O4—Ca1—O1—C10	91.65 (19)	O6—Ca2—O10—C19	−5.54 (18)
O3—Ca1—O1—C10	158.58 (18)	O21—Ca2—O10—C19	164.99 (18)
O5—Ca1—O1—C10	30.26 (18)	O7—Ca2—O10—C19	−6.4 (2)
O2—Ca1—O1—C10	−149.2 (2)	O20—Ca2—O10—C18	66.87 (17)
O14—Ca1—O1—C10	85.8 (4)	O17—Ca2—O10—C18	149.96 (18)
N1—Ca1—O1—C10	−77.87 (19)	O8—Ca2—O10—C18	−51.3 (2)
N2—Ca1—O1—C10	8.5 (3)	O18—Ca2—O10—C18	124.81 (18)
O15—Ca1—O2—C2	−142.67 (19)	O9—Ca2—O10—C18	−28.14 (17)
O11—Ca1—O2—C2	−94.66 (18)	O6—Ca2—O10—C18	−136.82 (19)
O12—Ca1—O2—C2	−147.90 (19)	O21—Ca2—O10—C18	33.70 (19)
O4—Ca1—O2—C2	63.27 (19)	O7—Ca2—O10—C18	−137.67 (17)
O3—Ca1—O2—C2	106.19 (19)	C10—O1—C1—C2	−178.9 (2)
O1—Ca1—O2—C2	−16.71 (17)	Ca1—O1—C1—C2	51.0 (3)
O5—Ca1—O2—C2	−17.4 (2)	C3—O2—C2—C1	176.9 (2)
O14—Ca1—O2—C2	151.63 (18)	Ca1—O2—C2—C1	47.8 (3)
N1—Ca1—O2—C2	−121.00 (19)	O1—C1—C2—O2	−63.6 (3)
N2—Ca1—O2—C2	177.50 (17)	C2—O2—C3—C4	−79.5 (3)
O15—Ca1—O2—C3	87.0 (2)	Ca1—O2—C3—C4	51.5 (3)
O11—Ca1—O2—C3	135.0 (2)	C5—O3—C4—C3	177.5 (2)
O12—Ca1—O2—C3	81.8 (2)	Ca1—O3—C4—C3	32.7 (3)
O4—Ca1—O2—C3	−67.1 (2)	O2—C3—C4—O3	−54.7 (4)
O3—Ca1—O2—C3	−24.14 (19)	C4—O3—C5—C6	−107.0 (3)
O1—Ca1—O2—C3	−147.0 (2)	Ca1—O3—C5—C6	39.9 (3)
O5—Ca1—O2—C3	−147.69 (19)	C7—O4—C6—C5	−168.0 (2)
O14—Ca1—O2—C3	21.3 (2)	Ca1—O4—C6—C5	47.8 (3)
N1—Ca1—O2—C3	108.7 (2)	O3—C5—C6—O4	−56.6 (3)
N2—Ca1—O2—C3	47.2 (2)	C6—O4—C7—C8	−171.8 (2)
O15—Ca1—O3—C4	−149.1 (2)	Ca1—O4—C7—C8	−29.7 (3)
O11—Ca1—O3—C4	−39.3 (3)	C9—O5—C8—C7	79.4 (3)
O12—Ca1—O3—C4	−73.0 (2)	Ca1—O5—C8—C7	−54.5 (3)
O4—Ca1—O3—C4	133.3 (2)	O4—C7—C8—O5	55.1 (3)
O1—Ca1—O3—C4	46.1 (2)	C8—O5—C9—C10	−162.0 (2)
O5—Ca1—O3—C4	115.3 (2)	Ca1—O5—C9—C10	−32.3 (3)
O2—Ca1—O3—C4	−5.7 (2)	C1—O1—C10—C9	169.6 (2)
O14—Ca1—O3—C4	−146.1 (2)	Ca1—O1—C10—C9	−59.0 (3)
N1—Ca1—O3—C4	−61.0 (2)	O5—C9—C10—O1	58.3 (3)
N2—Ca1—O3—C4	−146.4 (2)	C20—O6—C11—C12	177.5 (3)
O15—Ca1—O3—C5	66.5 (2)	Ca2—O6—C11—C12	−53.1 (3)
O11—Ca1—O3—C5	176.32 (18)	C13—O7—C12—C11	−172.3 (3)
O12—Ca1—O3—C5	142.61 (19)	Ca2—O7—C12—C11	−41.5 (3)
O4—Ca1—O3—C5	−11.02 (18)	O6—C11—C12—O7	60.7 (3)
O1—Ca1—O3—C5	−98.29 (19)	C12—O7—C13—C14	81.9 (3)
O5—Ca1—O3—C5	−29.1 (2)	Ca2—O7—C13—C14	−51.7 (3)
O2—Ca1—O3—C5	−150.1 (2)	C15—O8—C14—C13	177.6 (3)
O14—Ca1—O3—C5	69.54 (19)	Ca2—O8—C14—C13	−31.4 (4)
N1—Ca1—O3—C5	154.62 (18)	O7—C13—C14—O8	53.9 (4)
N2—Ca1—O3—C5	69.3 (2)	C14—O8—C15—C16	112.5 (3)
O15—Ca1—O4—C6	−144.81 (19)	Ca2—O8—C15—C16	−40.2 (3)
O11—Ca1—O4—C6	149.2 (2)	C17—O9—C16—C15	171.2 (2)
O12—Ca1—O4—C6	−81.5 (2)	Ca2—O9—C16—C15	−45.6 (3)
O3—Ca1—O4—C6	−20.82 (18)	O8—C15—C16—O9	55.1 (3)
O1—Ca1—O4—C6	84.35 (19)	C16—O9—C17—C18	168.9 (2)
O5—Ca1—O4—C6	144.3 (2)	Ca2—O9—C17—C18	27.7 (3)
O2—Ca1—O4—C6	21.5 (2)	C19—O10—C18—C17	−79.2 (3)
O14—Ca1—O4—C6	−96.92 (19)	Ca2—O10—C18—C17	55.3 (3)
N1—Ca1—O4—C6	−141.8 (3)	O9—C17—C18—O10	−53.8 (3)
N2—Ca1—O4—C6	−121.00 (19)	C18—O10—C19—C20	166.3 (2)
O15—Ca1—O4—C7	73.4 (2)	Ca2—O10—C19—C20	35.4 (3)
O11—Ca1—O4—C7	7.4 (3)	C11—O6—C20—C19	−173.9 (3)
O12—Ca1—O4—C7	136.7 (2)	Ca2—O6—C20—C19	55.5 (3)
O3—Ca1—O4—C7	−162.6 (2)	O10—C19—C20—O6	−58.7 (3)
O1—Ca1—O4—C7	−57.4 (2)	O13—N1—O11—Ca1	−176.4 (2)
O5—Ca1—O4—C7	2.51 (19)	O12—N1—O11—Ca1	4.0 (3)
O2—Ca1—O4—C7	−120.33 (19)	O15—Ca1—O11—N1	78.53 (16)
O14—Ca1—O4—C7	121.3 (2)	O12—Ca1—O11—N1	−2.28 (14)
N1—Ca1—O4—C7	76.4 (4)	O4—Ca1—O11—N1	148.06 (17)
N2—Ca1—O4—C7	97.2 (2)	O3—Ca1—O11—N1	−46.4 (2)
O15—Ca1—O5—C9	155.6 (2)	O1—Ca1—O11—N1	−142.84 (17)
O11—Ca1—O5—C9	78.07 (19)	O5—Ca1—O11—N1	152.58 (16)
O12—Ca1—O5—C9	105.08 (19)	O2—Ca1—O11—N1	−77.03 (16)
O4—Ca1—O5—C9	−104.24 (19)	O14—Ca1—O11—N1	44.16 (18)
O3—Ca1—O5—C9	−86.1 (2)	O13—N1—O12—Ca1	176.4 (2)
O1—Ca1—O5—C9	2.42 (17)	O11—N1—O12—Ca1	−4.0 (3)
O2—Ca1—O5—C9	3.1 (2)	O15—Ca1—O12—N1	−82.70 (16)
O14—Ca1—O5—C9	−167.10 (18)	O11—Ca1—O12—N1	2.29 (14)
N1—Ca1—O5—C9	90.52 (19)	O4—Ca1—O12—N1	−150.40 (15)
N2—Ca1—O5—C9	173.26 (18)	O3—Ca1—O12—N1	155.87 (15)
O15—Ca1—O5—C8	−73.51 (17)	O1—Ca1—O12—N1	45.37 (17)
O11—Ca1—O5—C8	−151.05 (17)	O5—Ca1—O12—N1	−32.6 (2)
O12—Ca1—O5—C8	−124.04 (17)	O2—Ca1—O12—N1	94.36 (16)
O4—Ca1—O5—C8	26.63 (16)	O14—Ca1—O12—N1	−135.08 (16)
O3—Ca1—O5—C8	44.8 (2)	O16—N2—O14—Ca1	−173.9 (2)
O1—Ca1—O5—C8	133.30 (18)	O15—N2—O14—Ca1	4.5 (2)
O2—Ca1—O5—C8	133.96 (17)	O15—Ca1—O14—N2	−2.72 (15)
O14—Ca1—O5—C8	−36.22 (18)	O11—Ca1—O14—N2	42.63 (18)
N1—Ca1—O5—C8	−138.60 (17)	O12—Ca1—O14—N2	78.85 (16)
N2—Ca1—O5—C8	−55.86 (17)	O4—Ca1—O14—N2	−109.13 (16)
O20—Ca2—O6—C20	4.4 (2)	O3—Ca1—O14—N2	−179.41 (17)
O17—Ca2—O6—C20	66.09 (18)	O1—Ca1—O14—N2	−103.1 (3)
O8—Ca2—O6—C20	−153.80 (18)	O5—Ca1—O14—N2	−51.48 (17)
O18—Ca2—O6—C20	100.27 (19)	O2—Ca1—O14—N2	137.54 (15)
O9—Ca2—O6—C20	−87.03 (18)	O16—N2—O15—Ca1	173.6 (2)
O10—Ca2—O6—C20	−27.06 (17)	O14—N2—O15—Ca1	−4.8 (3)
O7—Ca2—O6—C20	152.2 (2)	O11—Ca1—O15—N2	−135.74 (18)
O20—Ca2—O6—C11	−124.99 (18)	O12—Ca1—O15—N2	−81.66 (17)
O17—Ca2—O6—C11	−63.34 (18)	O4—Ca1—O15—N2	70.38 (17)
O8—Ca2—O6—C11	76.76 (18)	O3—Ca1—O15—N2	6.4 (2)
O18—Ca2—O6—C11	−29.16 (19)	O1—Ca1—O15—N2	167.03 (15)
O9—Ca2—O6—C11	143.54 (17)	O5—Ca1—O15—N2	134.68 (18)
O10—Ca2—O6—C11	−156.49 (19)	O2—Ca1—O15—N2	−86.8 (2)
O7—Ca2—O6—C11	22.77 (17)	O14—Ca1—O15—N2	2.74 (15)
O20—Ca2—O7—C13	−86.4 (2)	O19—N3—O17—Ca2	−166.3 (2)
O17—Ca2—O7—C13	−140.5 (2)	O18—N3—O17—Ca2	14.3 (3)
O8—Ca2—O7—C13	24.2 (2)	O20—Ca2—O17—N3	−90.30 (16)
O18—Ca2—O7—C13	−87.3 (2)	O8—Ca2—O17—N3	42.5 (2)
O9—Ca2—O7—C13	63.0 (2)	O18—Ca2—O17—N3	−8.11 (15)
O10—Ca2—O7—C13	144.2 (2)	O9—Ca2—O17—N3	−160.95 (16)
O6—Ca2—O7—C13	143.4 (2)	O10—Ca2—O17—N3	−164.52 (16)
O21—Ca2—O7—C13	−26.8 (2)	O6—Ca2—O17—N3	130.71 (17)
O20—Ca2—O7—C12	141.49 (19)	O21—Ca2—O17—N3	−50.97 (17)
O17—Ca2—O7—C12	87.35 (19)	O7—Ca2—O17—N3	64.72 (16)
O8—Ca2—O7—C12	−107.9 (2)	O19—N3—O18—Ca2	166.6 (2)
O18—Ca2—O7—C12	140.6 (2)	O17—N3—O18—Ca2	−14.0 (2)
O9—Ca2—O7—C12	−69.1 (2)	O20—Ca2—O18—N3	96.67 (16)
O10—Ca2—O7—C12	12.1 (2)	O17—Ca2—O18—N3	8.13 (15)
O6—Ca2—O7—C12	11.24 (18)	O8—Ca2—O18—N3	−142.44 (16)
O21—Ca2—O7—C12	−158.94 (18)	O9—Ca2—O18—N3	160.52 (15)
O20—Ca2—O8—C14	150.6 (2)	O10—Ca2—O18—N3	40.7 (2)
O17—Ca2—O8—C14	29.6 (3)	O6—Ca2—O18—N3	−34.88 (17)
O18—Ca2—O8—C14	67.7 (2)	O21—Ca2—O18—N3	148.93 (17)
O9—Ca2—O8—C14	−138.3 (3)	O7—Ca2—O18—N3	−83.82 (16)
O10—Ca2—O8—C14	−115.3 (2)	O22—N4—O20—Ca2	−172.0 (2)
O6—Ca2—O8—C14	−48.2 (2)	O21—N4—O20—Ca2	7.5 (2)
O21—Ca2—O8—C14	138.9 (3)	O17—Ca2—O20—N4	128.48 (17)
O7—Ca2—O8—C14	5.3 (2)	O8—Ca2—O20—N4	−18.66 (19)
O20—Ca2—O8—C15	−59.0 (2)	O18—Ca2—O20—N4	75.86 (16)
O17—Ca2—O8—C15	179.98 (19)	O9—Ca2—O20—N4	−78.75 (16)
O18—Ca2—O8—C15	−141.9 (2)	O10—Ca2—O20—N4	−143.95 (17)
O9—Ca2—O8—C15	12.1 (2)	O6—Ca2—O20—N4	−173.39 (14)
O10—Ca2—O8—C15	35.1 (2)	O21—Ca2—O20—N4	−4.31 (14)
O6—Ca2—O8—C15	102.2 (2)	O7—Ca2—O20—N4	75.0 (2)
O21—Ca2—O8—C15	−70.7 (2)	O22—N4—O21—Ca2	172.3 (2)
O7—Ca2—O8—C15	155.7 (2)	O20—N4—O21—Ca2	−7.2 (2)
O20—Ca2—O9—C16	145.57 (19)	O20—Ca2—O21—N4	4.30 (14)
O17—Ca2—O9—C16	−145.16 (19)	O17—Ca2—O21—N4	−49.60 (17)
O8—Ca2—O9—C16	19.05 (18)	O8—Ca2—O21—N4	171.53 (17)
O18—Ca2—O9—C16	83.7 (2)	O18—Ca2—O21—N4	−83.19 (16)
O10—Ca2—O9—C16	−141.2 (2)	O9—Ca2—O21—N4	102.47 (16)
O6—Ca2—O9—C16	−82.07 (19)	O10—Ca2—O21—N4	46.84 (17)
O21—Ca2—O9—C16	95.24 (18)	O7—Ca2—O21—N4	−140.76 (15)
O7—Ca2—O9—C16	−19.2 (2)

Acknowledgements

We thank the EPSRC for financial support (MDB).

References

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Volume 61| Part 6| June 2005| Pages m1015-m1017

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