Crystal structure of poly[μ-acetato-bis­[μ-2-oxo-2-(quinolin-8-yl)ethano­ato]tris­odium]

Nicholls, R.L.; Pask, C.M.; Nguyen, B.

doi:10.1107/S1600536814023423

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages m385-m386

doi:10.1107/S1600536814023423

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Crystal structure of poly[μ-acetato-bis[μ-2-oxo-2-(quinolin-8-yl)ethanoato]trisodium]

Rachel L. Nicholls,^a Christopher M. Pask ^a and Bao Nguyen ^a ^*

^aSchool of Chemistry, University of Leeds, Woodhouse Lane, Leeds, LS2 9JT, England
^*Correspondence e-mail: B.Nguyen@leeds.ac.uk

Edited by T. J. Prior, University of Hull, England (Received 6 October 2014; accepted 23 October 2014; online 31 October 2014)

The title compound [Na₃(C₁₁H₆NO₃)₂(C₂H₃O₂)]_n, crystallized through diffusion of diethyl ether into methanol as needles. There are three crystallographically independent Na⁺ cations present, each exhibiting a distorted octahedral coordination geometry, two through coordination by five O atoms and one N atom, and one through coordination by six O atoms. A series of intermolecular O⋯Na and N⋯Na contacts leads to the formation of chains along the a-axis direction.

Keywords: crystal structure; keto acid; sodium; acetate.

CCDC reference: 1030741

1. Related literature

The sodium salt of 2-oxo-2-(quinolin-8-yl)ethanoic acid was prepared as an authentic product during a catalytic process development within our group. Ethyl 2-oxo-2-(quinolin-8-yl)ethanoate was prepared by a literature procedure (Crespo-Peña et al., 2012 ) and then hydrolysed under basic conditions to yield the title compound. For sodium salts of keto-acids, see; Lis & Matuszewski (1984 ); Jain et al. (1969 ); Tavale et al. (1961 , 1964 ); Rach et al. (1988 ). A similar Na⋯C=N(quinoline) interaction is observed in a previously published samarium Schiff base complex (Li et al., 2008 ).

2. Experimental

2.1. Crystal data

[Na₃(C₁₁H₆NO₃)₂(C₂H₃O₂)]
M_r = 528.35
Monoclinic, P 2₁ /c
a = 6.1101 (5) Å
b = 22.7075 (19) Å
c = 16.1587 (12) Å
β = 94.626 (7)°
V = 2234.6 (3) Å³
Z = 4
Cu Kα radiation
μ = 1.50 mm⁻¹
T = 120 K
0.19 × 0.04 × 0.03 mm

2.2. Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014 ), based on expressions derived by Clark & Reid (1995 )] T_min = 0.887, T_max = 0.971
7799 measured reflections
3943 independent reflections
2557 reflections with I > 2σ(I)
R_int = 0.059

2.3. Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.130
S = 0.99
3943 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1030741

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814023423/pj2016sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023423/pj2016Isup2.hkl

checkCIF report

Comment top

The sodium salt (1) of 2-oxo-2-(quinolin-8-yl)ethanoic acid was prepared as an authentic product during a catalytic process development within our group. Ethyl 2-oxo-2-(quinolin-8-yl)ethanoate was prepared by a literature procedure (Crespo-Peña et al., 2012) and then hydrolysed under basic conditions to yield the title compound.

The asymmetric unit of 1 (Fig. 1) contains two crystallographically independent 2-oxo-2-(quinolin-8-yl)ethanoate anions, one acetate anion and three crystallographically independent sodium cations. Each sodium cation exhibits distorted octahedral geometry. One sodium cation (Na36) is coordinated by six oxygen atoms from the oxo-2'-quinolin-8'-yl-ethanoate and acetate ions. Na···O bond distances are in the range 2.290 (3) to 2.610 (3) Å. The other two sodium cations (Na35, Na37) are coordinated by five oxygen atoms (2.272 (3)-2.727 (3) Å) and what appears to be an η₂ interaction with a C=N of the quinoline ring (Na···N = 2.769 (3), 2.814 (3); Na···C = 3.035 (4), 3.073 (4)). A similar Na···C=N (quinoline) interaction is observed in a previously published samarium Schiff base complex (Li et al., 2008), although this is somewhat shorter than that observed in 1. Na···O bond lengths are comparable to previously published sodium salts of keto acids (Lis et al., 1984, Jain et al., 1969, Tavale et al., 1961, 1964, Rach et al., 1988).

These Na···O interactions lead to the formation of one-dimensional chains along the crystallographic a-axis (Fig. 2). The quinoline rings of the oxo(8-quinolyl)acetate groups and methyl groups of acetate ions appear to act as a hydrophobic sheath, encapsulating the Na···O core of the chains, keeping them separated in the solid state. (Fig. 3).

Experimental top

A solution of ethyl 2-oxo-2-(quinolin-8-yl)ethanoate (217 mg, 0.947 mmol) in methanol (3mL) was cooled to 0 °C and aqueous 2M NaOH (3 mL) added and stirred at room temperature for 90 min. The methanol was removed under vacuum and the remaining aqueous solution was washed at pH 9 with ethyl acetate (2 x 20 mL). The aqueous solution was acidified to pH 5 with 1M HCl and washed with ethyl acetate (2 x 20 mL). The remaining aqueous solution was reduced under vacuum to give a white solid (0.231 g) which was dissolved in methanol and filtered to remove NaCl. The product was recrystallised through diffusion of diethyl ether into a solution of the product in a minimum amount of methanol over three days to afford colourless needles.

Refinement top

No special refinement procedures were applied to this crystal structure. All hydrogen atoms were placed in calculated positions and refined isotropically using a riding model.

Related literature top

The sodium salt of 2-oxo-2-(quinolin-8-yl)ethanoic acid was prepared as an authentic product during a catalytic process development within our group. Ethyl 2-oxo-2-(quinolin-8-yl)ethanoate was prepared by a literature procedure (Crespo-Peña et al., 2012) and then hydrolysed under basic conditions to yield the title compound. For sodium salts of keto-acids, see; Lis & Matuszewski (1984); Jain et al. (1969); Tavale et al. (1961), (1964); Rach et al. (1988). A similar Na···C═ N(quinoline) interaction is observed in a previously published samarium Schiff base complex (Li et al., 2008).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

The asymmetric unit of (1) showing the labelling scheme. Displacement ellipsoids are at the 50% probability level. Hydrogen atoms have been omitted for clarity.

Partial packing diagram of (1) showing the one-dimensional chain along the crystallographic a-axis. Displacement ellipsoids are at the 50% probability level.

Partial packing diagram of (1) viewed on the bc plane. Displacement ellipsoids are at the 50% probability level.

Poly[µ-acetato-bis[µ-2-oxo-2-(quinolin-8-yl)ethanoato]trisodium] top

Crystal data top

[Na₃(C₁₁H₆NO₃)₂(C₂H₃O₂)]	F(000) = 1080
M_r = 528.35	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 6.1101 (5) Å	Cell parameters from 1524 reflections
b = 22.7075 (19) Å	θ = 5.5–72.4°
c = 16.1587 (12) Å	µ = 1.50 mm⁻¹
β = 94.626 (7)°	T = 120 K
V = 2234.6 (3) Å³	Needle, colourless
Z = 4	0.19 × 0.04 × 0.03 mm

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3943 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	2557 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
Detector resolution: 10.6191 pixels mm^-1	θ_max = 66.6°, θ_min = 3.4°
ω scans	h = −4→7
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]	k = −25→26
T_min = 0.887, T_max = 0.971	l = −18→19
7799 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0475P)²] where P = (F_o² + 2F_c²)/3
3943 reflections	(Δ/σ)_max < 0.001
335 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

[Na₃(C₁₁H₆NO₃)₂(C₂H₃O₂)]	V = 2234.6 (3) Å³
M_r = 528.35	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 6.1101 (5) Å	µ = 1.50 mm⁻¹
b = 22.7075 (19) Å	T = 120 K
c = 16.1587 (12) Å	0.19 × 0.04 × 0.03 mm
β = 94.626 (7)°

Data collection top

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	3943 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]	2557 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.971	R_int = 0.059
7799 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 0.99	Δρ_max = 0.25 e Å⁻³
3943 reflections	Δρ_min = −0.29 e Å⁻³
335 parameters

Special details top

Experimental. Absorption correction: CrysAlisPro, Agilent Technologies, Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET) (compiled Mar 27 2014,17:12:48) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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

	x	y	z	U_iso*/U_eq
N1	0.2460 (5)	0.59015 (12)	0.32073 (16)	0.0248 (6)
C2	0.0893 (6)	0.56634 (17)	0.3616 (2)	0.0324 (8)
H2	0.0647	0.5261	0.3557	0.039*
C3	−0.0423 (7)	0.59804 (19)	0.4134 (2)	0.0447 (11)
H3	−0.1491	0.5789	0.4413	0.054*
C4	−0.0117 (7)	0.65702 (19)	0.4222 (2)	0.0428 (10)
H4	−0.0980	0.6786	0.4561	0.051*
C5	0.1503 (5)	0.68536 (16)	0.3801 (2)	0.0267 (7)
C6	0.2792 (5)	0.65001 (14)	0.33027 (19)	0.0220 (7)
C7	0.1939 (6)	0.74641 (16)	0.3868 (2)	0.0303 (8)
H7	0.1080	0.7698	0.4186	0.036*
C8	0.3585 (6)	0.77153 (15)	0.3477 (2)	0.0281 (8)
H8	0.3841	0.8118	0.3524	0.034*
C9	0.4899 (6)	0.73642 (14)	0.3001 (2)	0.0259 (7)
H9	0.6058	0.7538	0.2752	0.031*
C10	0.4523 (5)	0.67691 (13)	0.28926 (18)	0.0197 (6)
C11	0.5912 (5)	0.64329 (14)	0.23363 (19)	0.0204 (7)
C12	0.5049 (5)	0.58940 (13)	0.18503 (18)	0.0180 (6)
O13	0.7770 (4)	0.66025 (11)	0.22217 (15)	0.0303 (6)
O14	0.3382 (4)	0.59685 (10)	0.13640 (13)	0.0237 (5)
O15	0.6225 (4)	0.54440 (10)	0.19491 (14)	0.0255 (5)
N16	0.2494 (4)	0.56492 (12)	−0.33221 (16)	0.0245 (6)
C17	0.4040 (6)	0.53700 (16)	−0.3695 (2)	0.0285 (8)
H17	0.4232	0.4970	−0.3590	0.034*
C18	0.5401 (7)	0.56398 (17)	−0.4235 (2)	0.0371 (9)
H18	0.6454	0.5422	−0.4487	0.045*
C19	0.5161 (7)	0.62277 (17)	−0.4390 (2)	0.0385 (9)
H19	0.6037	0.6413	−0.4755	0.046*
C20	0.3589 (6)	0.65517 (15)	−0.3995 (2)	0.0268 (7)
C21	0.2230 (5)	0.62401 (14)	−0.34723 (18)	0.0200 (6)
C22	0.3271 (6)	0.71665 (16)	−0.4110 (2)	0.0310 (8)
H22	0.4179	0.7375	−0.4440	0.037*
C23	0.1646 (6)	0.74553 (16)	−0.3741 (2)	0.0307 (8)
H23	0.1461	0.7859	−0.3816	0.037*
C24	0.0249 (5)	0.71412 (14)	−0.32455 (19)	0.0241 (7)
H24	−0.0893	0.7338	−0.3017	0.029*
C25	0.0544 (5)	0.65465 (14)	−0.30924 (18)	0.0208 (7)
C26	−0.0895 (5)	0.62462 (13)	−0.25169 (18)	0.0200 (6)
C27	−0.0049 (5)	0.57333 (13)	−0.19636 (19)	0.0182 (6)
O28	−0.2754 (4)	0.64243 (11)	−0.24306 (15)	0.0288 (5)
O29	0.1611 (3)	0.58346 (10)	−0.14860 (13)	0.0219 (5)
O30	−0.1234 (3)	0.52831 (10)	−0.20085 (13)	0.0232 (5)
C31	0.7331 (9)	0.65337 (18)	−0.0025 (3)	0.0526 (12)
H31A	0.5884	0.6654	0.0096	0.079*
H31B	0.7644	0.6685	−0.0557	0.079*
H31C	0.8387	0.6684	0.0395	0.079*
C32	0.7452 (5)	0.58759 (14)	−0.00364 (19)	0.0205 (7)
O33	0.9040 (4)	0.56211 (12)	0.03523 (14)	0.0312 (6)
O34	0.5933 (4)	0.55990 (11)	−0.04300 (14)	0.0278 (5)
Na35	0.50542 (19)	0.54983 (5)	−0.18100 (7)	0.0201 (3)
Na36	0.2478 (2)	0.54062 (6)	−0.00310 (8)	0.0247 (3)
Na37	0.99681 (19)	0.56515 (5)	0.17420 (7)	0.0198 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0263 (16)	0.0231 (15)	0.0257 (13)	−0.0049 (11)	0.0074 (11)	−0.0003 (12)
C2	0.041 (2)	0.0288 (19)	0.0285 (17)	−0.0146 (15)	0.0098 (15)	−0.0036 (15)
C3	0.044 (2)	0.053 (3)	0.041 (2)	−0.020 (2)	0.0246 (18)	−0.013 (2)
C4	0.041 (2)	0.049 (3)	0.041 (2)	−0.0106 (18)	0.0226 (18)	−0.0217 (19)
C5	0.0249 (19)	0.0326 (19)	0.0230 (16)	−0.0020 (14)	0.0042 (13)	−0.0095 (14)
C6	0.0215 (17)	0.0213 (17)	0.0228 (15)	−0.0020 (12)	0.0001 (12)	−0.0012 (13)
C7	0.0286 (19)	0.0312 (19)	0.0310 (18)	0.0072 (14)	0.0005 (14)	−0.0131 (15)
C8	0.040 (2)	0.0166 (16)	0.0269 (16)	0.0015 (14)	−0.0046 (15)	−0.0049 (14)
C9	0.0260 (18)	0.0201 (17)	0.0314 (17)	−0.0006 (13)	0.0007 (13)	−0.0020 (14)
C10	0.0200 (17)	0.0187 (16)	0.0199 (14)	−0.0002 (12)	−0.0030 (12)	−0.0037 (13)
C11	0.0175 (17)	0.0204 (16)	0.0237 (15)	−0.0006 (12)	0.0043 (12)	−0.0002 (13)
C12	0.0168 (16)	0.0168 (16)	0.0215 (14)	−0.0002 (12)	0.0080 (12)	0.0007 (12)
O13	0.0193 (13)	0.0291 (13)	0.0431 (13)	−0.0082 (9)	0.0065 (10)	−0.0104 (11)
O14	0.0174 (12)	0.0270 (12)	0.0267 (11)	−0.0040 (9)	0.0018 (9)	−0.0018 (10)
O15	0.0183 (12)	0.0200 (12)	0.0395 (13)	0.0009 (9)	0.0108 (10)	−0.0027 (10)
N16	0.0279 (16)	0.0189 (14)	0.0277 (14)	0.0010 (11)	0.0087 (11)	0.0011 (12)
C17	0.034 (2)	0.0255 (18)	0.0274 (16)	0.0027 (14)	0.0107 (14)	−0.0026 (14)
C18	0.041 (2)	0.034 (2)	0.0386 (19)	0.0038 (17)	0.0206 (17)	−0.0013 (17)
C19	0.045 (2)	0.040 (2)	0.0339 (19)	−0.0035 (17)	0.0211 (17)	0.0055 (18)
C20	0.0318 (19)	0.0251 (18)	0.0242 (15)	−0.0025 (14)	0.0059 (14)	0.0033 (14)
C21	0.0219 (17)	0.0211 (16)	0.0170 (14)	−0.0043 (12)	0.0012 (12)	0.0001 (12)
C22	0.035 (2)	0.030 (2)	0.0284 (17)	−0.0062 (15)	0.0047 (14)	0.0106 (15)
C23	0.036 (2)	0.0226 (18)	0.0320 (18)	−0.0030 (14)	−0.0043 (15)	0.0071 (15)
C24	0.0265 (18)	0.0204 (17)	0.0246 (16)	0.0025 (13)	−0.0027 (13)	0.0019 (13)
C25	0.0213 (17)	0.0215 (17)	0.0193 (14)	−0.0005 (12)	−0.0008 (12)	0.0008 (12)
C26	0.0201 (17)	0.0190 (16)	0.0206 (14)	0.0004 (12)	0.0007 (12)	−0.0029 (13)
C27	0.0133 (16)	0.0181 (16)	0.0245 (15)	0.0017 (11)	0.0085 (12)	−0.0015 (13)
O28	0.0186 (13)	0.0308 (13)	0.0375 (13)	0.0084 (10)	0.0045 (10)	0.0062 (11)
O29	0.0153 (12)	0.0242 (12)	0.0258 (11)	0.0035 (8)	−0.0010 (9)	0.0005 (9)
O30	0.0169 (12)	0.0212 (12)	0.0323 (12)	−0.0004 (9)	0.0070 (9)	0.0016 (10)
C31	0.084 (3)	0.025 (2)	0.046 (2)	−0.007 (2)	−0.013 (2)	0.0025 (18)
C32	0.0135 (15)	0.0274 (18)	0.0205 (14)	−0.0018 (12)	0.0004 (12)	0.0025 (13)
O33	0.0159 (12)	0.0532 (16)	0.0243 (11)	0.0085 (10)	0.0012 (9)	0.0068 (11)
O34	0.0150 (12)	0.0415 (15)	0.0269 (11)	−0.0051 (9)	0.0013 (9)	−0.0098 (11)
Na35	0.0146 (6)	0.0211 (6)	0.0245 (6)	0.0003 (4)	0.0016 (5)	−0.0015 (5)
Na36	0.0124 (6)	0.0279 (7)	0.0341 (7)	0.0005 (5)	0.0035 (5)	0.0016 (5)
Na37	0.0149 (6)	0.0221 (6)	0.0224 (6)	−0.0002 (4)	0.0019 (4)	0.0006 (5)

Geometric parameters (Å, º) top

N1—C2	1.321 (4)	C24—H24	0.9300
N1—C6	1.381 (4)	C24—C25	1.382 (5)
N1—Na37ⁱ	2.769 (3)	C25—C26	1.495 (4)
C2—H2	0.9300	C26—C27	1.532 (4)
C2—C3	1.406 (5)	C26—O28	1.224 (4)
C2—Na37ⁱ	3.035 (4)	C27—O29	1.245 (4)
C3—H3	0.9300	C27—O30	1.252 (4)
C3—C4	1.358 (6)	C27—Na35ⁱ	3.069 (3)
C4—H4	0.9300	O28—Na35ⁱ	2.727 (3)
C4—C5	1.402 (5)	O29—Na35	2.337 (2)
C5—C6	1.419 (5)	O29—Na36	2.560 (2)
C5—C7	1.414 (5)	O30—Na35ⁱ	2.367 (2)
C6—C10	1.430 (5)	O30—Na37ⁱⁱ	2.288 (2)
C7—H7	0.9300	C31—H31A	0.9600
C7—C8	1.355 (5)	C31—H31B	0.9600
C8—H8	0.9300	C31—H31C	0.9600
C8—C9	1.404 (5)	C31—C32	1.496 (5)
C9—H9	0.9300	C32—O33	1.254 (4)
C9—C10	1.380 (5)	C32—O34	1.251 (4)
C10—C11	1.495 (4)	C32—Na36ⁱⁱ	2.914 (4)
C11—C12	1.525 (4)	O33—Na36ⁱⁱ	2.549 (3)
C11—O13	1.227 (4)	O33—Na36ⁱⁱⁱ	2.290 (3)
C12—O14	1.247 (4)	O33—Na37	2.272 (2)
C12—O15	1.252 (4)	O34—Na35	2.263 (2)
C12—Na37	3.074 (3)	O34—Na36	2.299 (2)
O13—Na37	2.690 (3)	O34—Na36ⁱⁱ	2.567 (3)
O14—Na36	2.610 (3)	Na35—O15ⁱⁱ	2.283 (2)
O14—Na37ⁱ	2.334 (2)	Na35—C27ⁱⁱⁱ	3.069 (3)
O15—Na35ⁱⁱ	2.283 (2)	Na35—O28ⁱⁱⁱ	2.727 (3)
O15—Na37	2.385 (2)	Na35—O30ⁱⁱⁱ	2.367 (2)
N16—C17	1.322 (4)	Na35—Na36ⁱⁱ	3.8233 (18)
N16—C21	1.371 (4)	Na35—Na36	3.3934 (17)
N16—Na35	2.814 (3)	Na36—C32ⁱⁱ	2.913 (4)
C17—H17	0.9300	Na36—O33ⁱⁱ	2.549 (3)
C17—C18	1.395 (5)	Na36—O33ⁱ	2.290 (3)
C17—Na35	3.073 (4)	Na36—O34ⁱⁱ	2.567 (3)
C18—H18	0.9300	Na36—Na35ⁱⁱ	3.8233 (18)
C18—C19	1.364 (6)	Na36—Na36^iv	3.554 (3)
C19—H19	0.9300	Na36—Na36ⁱⁱ	3.586 (3)
C19—C20	1.403 (5)	Na36—Na37ⁱ	3.4027 (16)
C20—C21	1.420 (4)	Na37—N1ⁱⁱⁱ	2.769 (3)
C20—C22	1.420 (5)	Na37—C2ⁱⁱⁱ	3.035 (4)
C21—C25	1.423 (4)	Na37—O14ⁱⁱⁱ	2.334 (2)
C22—H22	0.9300	Na37—O30ⁱⁱ	2.288 (2)
C22—C23	1.366 (5)	Na37—Na36ⁱⁱⁱ	3.4026 (16)
C23—H23	0.9300	Na37—Na36ⁱⁱ	3.8705 (18)
C23—C24	1.410 (5)

C2—N1—C6	116.9 (3)	O29—Na35—Na36ⁱⁱ	107.87 (7)
C2—N1—Na37ⁱ	88.4 (2)	O29—Na35—Na37^v	154.51 (7)
C6—N1—Na37ⁱ	111.3 (2)	O29—Na35—Na37ⁱⁱ	60.34 (6)
N1—C2—H2	118.0	O30ⁱⁱⁱ—Na35—N16	112.27 (9)
N1—C2—C3	124.1 (3)	O30ⁱⁱⁱ—Na35—C17	87.99 (9)
N1—C2—Na37ⁱ	65.77 (18)	O30ⁱⁱⁱ—Na35—C27ⁱⁱⁱ	22.17 (8)
C3—C2—H2	118.0	O30ⁱⁱⁱ—Na35—O28ⁱⁱⁱ	66.74 (8)
C3—C2—Na37ⁱ	122.0 (3)	O30ⁱⁱⁱ—Na35—Na36	128.10 (7)
Na37ⁱ—C2—H2	82.7	O30ⁱⁱⁱ—Na35—Na36ⁱⁱ	70.88 (6)
C2—C3—H3	120.4	O30ⁱⁱⁱ—Na35—Na37ⁱⁱ	127.51 (7)
C4—C3—C2	119.1 (4)	O30ⁱⁱⁱ—Na35—Na37^v	30.11 (6)
C4—C3—H3	120.4	O34—Na35—O15ⁱⁱ	104.12 (10)
C3—C4—H4	120.0	O34—Na35—N16	156.15 (10)
C3—C4—C5	119.9 (3)	O34—Na35—C17	177.87 (10)
C5—C4—H4	120.0	O34—Na35—C27ⁱⁱⁱ	84.64 (9)
C4—C5—C6	117.5 (3)	O34—Na35—O28ⁱⁱⁱ	101.53 (9)
C4—C5—C7	123.3 (3)	O34—Na35—O29	83.84 (9)
C7—C5—C6	119.2 (3)	O34—Na35—O30ⁱⁱⁱ	90.03 (9)
N1—C6—C5	122.5 (3)	O34—Na35—Na36ⁱⁱ	40.55 (7)
N1—C6—C10	118.4 (3)	O34—Na35—Na36	42.34 (6)
C5—C6—C10	119.1 (3)	O34—Na35—Na37ⁱⁱ	99.15 (7)
C5—C7—H7	119.4	O34—Na35—Na37^v	85.38 (7)
C8—C7—C5	121.3 (3)	Na36—Na35—Na36ⁱⁱ	59.24 (4)
C8—C7—H7	119.4	Na36—Na35—Na37^v	109.87 (4)
C7—C8—H8	120.2	Na36ⁱⁱ—Na35—Na37ⁱⁱ	83.36 (3)
C7—C8—C9	119.6 (3)	Na36—Na35—Na37ⁱⁱ	62.07 (3)
C9—C8—H8	120.2	Na36ⁱⁱ—Na35—Na37^v	51.48 (3)
C8—C9—H9	119.0	Na37^v—Na35—Na37ⁱⁱ	98.91 (4)
C10—C9—C8	122.0 (3)	O14—Na36—C32ⁱⁱ	117.07 (9)
C10—C9—H9	119.0	O14—Na36—Na35	128.39 (7)
C6—C10—C11	122.5 (3)	O14—Na36—Na35ⁱⁱ	63.15 (6)
C9—C10—C6	118.8 (3)	O14—Na36—Na36^iv	110.54 (7)
C9—C10—C11	118.7 (3)	O14—Na36—Na36ⁱⁱ	96.09 (7)
C10—C11—C12	122.0 (3)	O14—Na36—Na37ⁱ	43.22 (5)
O13—C11—C10	120.5 (3)	O29—Na36—O14	128.38 (9)
O13—C11—C12	117.4 (3)	O29—Na36—C32ⁱⁱ	114.54 (9)
C11—C12—Na37	82.75 (17)	O29—Na36—O34ⁱⁱ	130.52 (9)
O14—C12—C11	116.5 (3)	O29—Na36—Na35	43.48 (5)
O14—C12—O15	128.5 (3)	O29—Na36—Na35ⁱⁱ	163.36 (7)
O14—C12—Na37	137.8 (2)	O29—Na36—Na36^iv	96.27 (7)
O15—C12—C11	114.7 (3)	O29—Na36—Na36ⁱⁱ	109.56 (7)
O15—C12—Na37	46.18 (15)	O29—Na36—Na37ⁱ	129.57 (7)
C11—O13—Na37	106.3 (2)	C32ⁱⁱ—Na36—Na35	94.98 (7)
C12—O14—Na36	125.7 (2)	C32ⁱⁱ—Na36—Na35ⁱⁱ	55.28 (7)
C12—O14—Na37ⁱ	119.68 (19)	C32ⁱⁱ—Na36—Na36^iv	59.35 (7)
Na37ⁱ—O14—Na36	86.79 (8)	C32ⁱⁱ—Na36—Na36ⁱⁱ	58.33 (7)
C12—O15—Na35ⁱⁱ	124.3 (2)	C32ⁱⁱ—Na36—Na37ⁱ	97.95 (7)
C12—O15—Na37	111.58 (19)	O33ⁱⁱ—Na36—O14	132.21 (9)
Na35ⁱⁱ—O15—Na37	119.72 (10)	O33ⁱ—Na36—O14	78.29 (9)
C17—N16—C21	117.8 (3)	O33ⁱⁱ—Na36—O29	96.64 (8)
C17—N16—Na35	88.3 (2)	O33ⁱ—Na36—O29	92.35 (8)
C21—N16—Na35	108.79 (19)	O33ⁱⁱ—Na36—C32ⁱⁱ	25.43 (8)
N16—C17—H17	118.0	O33ⁱ—Na36—C32ⁱⁱ	102.34 (10)
N16—C17—C18	123.9 (3)	O33ⁱ—Na36—O33ⁱⁱ	85.60 (10)
N16—C17—Na35	66.26 (18)	O33ⁱ—Na36—O34	156.71 (11)
C18—C17—H17	118.0	O33ⁱ—Na36—O34ⁱⁱ	116.40 (10)
C18—C17—Na35	119.8 (3)	O33ⁱⁱ—Na36—O34ⁱⁱ	50.81 (7)
Na35—C17—H17	84.3	O33ⁱⁱ—Na36—Na35ⁱⁱ	77.35 (6)
C17—C18—H18	120.5	O33ⁱ—Na36—Na35	135.58 (8)
C19—C18—C17	118.9 (3)	O33ⁱ—Na36—Na35ⁱⁱ	102.52 (7)
C19—C18—H18	120.5	O33ⁱⁱ—Na36—Na35	94.01 (7)
C18—C19—H19	120.1	O33ⁱⁱ—Na36—Na36ⁱⁱ	80.37 (7)
C18—C19—C20	119.9 (3)	O33ⁱ—Na36—Na36^iv	45.64 (8)
C20—C19—H19	120.1	O33ⁱ—Na36—Na36ⁱⁱ	155.10 (9)
C19—C20—C21	117.6 (3)	O33ⁱⁱ—Na36—Na36^iv	39.97 (6)
C19—C20—C22	123.2 (3)	O33ⁱⁱ—Na36—Na37ⁱ	98.05 (7)
C22—C20—C21	119.2 (3)	O33ⁱ—Na36—Na37ⁱ	41.57 (6)
N16—C21—C20	121.8 (3)	O34ⁱⁱ—Na36—O14	97.80 (8)
N16—C21—C25	118.8 (3)	O34—Na36—O14	90.80 (8)
C20—C21—C25	119.4 (3)	O34—Na36—O29	78.28 (8)
C20—C22—H22	119.6	O34ⁱⁱ—Na36—C32ⁱⁱ	25.40 (8)
C23—C22—C20	120.8 (3)	O34—Na36—C32ⁱⁱ	100.94 (10)
C23—C22—H22	119.6	O34—Na36—O33ⁱⁱ	116.40 (10)
C22—C23—H23	120.0	O34—Na36—O34ⁱⁱ	85.21 (10)
C22—C23—C24	120.0 (3)	O34ⁱⁱ—Na36—Na35ⁱⁱ	34.96 (5)
C24—C23—H23	120.0	O34ⁱⁱ—Na36—Na35	96.33 (6)
C23—C24—H24	119.3	O34—Na36—Na35ⁱⁱ	90.41 (7)
C25—C24—C23	121.3 (3)	O34—Na36—Na35	41.53 (6)
C25—C24—H24	119.3	O34—Na36—Na36ⁱⁱ	45.51 (7)
C21—C25—C26	121.9 (3)	O34ⁱⁱ—Na36—Na36ⁱⁱ	39.70 (6)
C24—C25—C21	119.3 (3)	O34ⁱⁱ—Na36—Na36^iv	80.41 (7)
C24—C25—C26	118.8 (3)	O34—Na36—Na36^iv	155.59 (9)
C25—C26—C27	121.5 (3)	O34ⁱⁱ—Na36—Na37ⁱ	94.98 (6)
O28—C26—C25	121.2 (3)	O34—Na36—Na37ⁱ	133.75 (8)
O28—C26—C27	117.2 (3)	Na35—Na36—Na35ⁱⁱ	120.76 (4)
C26—C27—Na35ⁱ	83.92 (17)	Na35—Na36—Na36ⁱⁱ	66.36 (4)
O29—C27—C26	116.2 (3)	Na35—Na36—Na36^iv	120.68 (6)
O29—C27—O30	128.7 (3)	Na35—Na36—Na37ⁱ	167.03 (5)
O29—C27—Na35ⁱ	137.1 (2)	Na36ⁱⁱ—Na36—Na35ⁱⁱ	54.40 (4)
O30—C27—C26	114.9 (3)	Na36^iv—Na36—Na35ⁱⁱ	89.01 (5)
O30—C27—Na35ⁱ	45.52 (15)	Na36^iv—Na36—Na36ⁱⁱ	117.67 (7)
C26—O28—Na35ⁱ	105.9 (2)	Na37ⁱ—Na36—Na35ⁱⁱ	66.99 (4)
C27—O29—Na35	120.25 (19)	Na37ⁱ—Na36—Na36ⁱⁱ	120.36 (6)
C27—O29—Na36	126.7 (2)	Na37ⁱ—Na36—Na36^iv	67.57 (4)
Na35—O29—Na36	87.60 (8)	N1ⁱⁱⁱ—Na37—C2ⁱⁱⁱ	25.79 (9)
C27—O30—Na35ⁱ	112.32 (19)	N1ⁱⁱⁱ—Na37—C12	112.78 (9)
C27—O30—Na37ⁱⁱ	124.2 (2)	N1ⁱⁱⁱ—Na37—Na35ⁱⁱ	118.43 (7)
Na37ⁱⁱ—O30—Na35ⁱ	118.63 (10)	N1ⁱⁱⁱ—Na37—Na35^v	75.29 (7)
H31A—C31—H31B	109.5	N1ⁱⁱⁱ—Na37—Na36ⁱⁱⁱ	119.97 (7)
H31A—C31—H31C	109.5	N1ⁱⁱⁱ—Na37—Na36ⁱⁱ	153.15 (7)
H31B—C31—H31C	109.5	C2ⁱⁱⁱ—Na37—C12	92.63 (10)
C32—C31—H31A	109.5	C2ⁱⁱⁱ—Na37—Na35ⁱⁱ	93.41 (7)
C32—C31—H31B	109.5	C2ⁱⁱⁱ—Na37—Na35^v	84.17 (8)
C32—C31—H31C	109.5	C2ⁱⁱⁱ—Na37—Na36ⁱⁱⁱ	141.35 (9)
C31—C32—Na36ⁱⁱ	176.4 (3)	C2ⁱⁱⁱ—Na37—Na36ⁱⁱ	138.44 (8)
O33—C32—C31	119.4 (3)	C12—Na37—Na35ⁱⁱ	50.62 (6)
O33—C32—Na36ⁱⁱ	60.79 (18)	C12—Na37—Na35^v	149.24 (7)
O34—C32—C31	118.2 (3)	C12—Na37—Na36ⁱⁱⁱ	125.90 (7)
O34—C32—O33	122.3 (3)	C12—Na37—Na36ⁱⁱ	80.15 (6)
O34—C32—Na36ⁱⁱ	61.64 (18)	O13—Na37—N1ⁱⁱⁱ	80.90 (8)
C32—O33—Na36ⁱⁱⁱ	130.7 (2)	O13—Na37—C2ⁱⁱⁱ	76.26 (10)
C32—O33—Na36ⁱⁱ	93.8 (2)	O13—Na37—C12	47.68 (8)
C32—O33—Na37	127.0 (2)	O13—Na37—Na35^v	155.72 (7)
Na36ⁱⁱⁱ—O33—Na36ⁱⁱ	94.40 (10)	O13—Na37—Na35ⁱⁱ	96.49 (6)
Na37—O33—Na36ⁱⁱ	106.67 (10)	O13—Na37—Na36ⁱⁱ	122.07 (7)
Na37—O33—Na36ⁱⁱⁱ	96.46 (10)	O13—Na37—Na36ⁱⁱⁱ	130.05 (7)
C32—O34—Na35	131.2 (2)	O14ⁱⁱⁱ—Na37—N1ⁱⁱⁱ	73.69 (8)
C32—O34—Na36ⁱⁱ	93.0 (2)	O14ⁱⁱⁱ—Na37—C2ⁱⁱⁱ	99.20 (9)
C32—O34—Na36	127.8 (2)	O14ⁱⁱⁱ—Na37—C12	149.10 (9)
Na35—O34—Na36ⁱⁱ	104.49 (10)	O14ⁱⁱⁱ—Na37—O13	107.78 (9)
Na35—O34—Na36	96.13 (9)	O14ⁱⁱⁱ—Na37—O15	170.06 (10)
Na36—O34—Na36ⁱⁱ	94.80 (10)	O14ⁱⁱⁱ—Na37—Na35^v	61.01 (6)
O15ⁱⁱ—Na35—N16	82.34 (9)	O14ⁱⁱⁱ—Na37—Na35ⁱⁱ	154.67 (7)
O15ⁱⁱ—Na35—C17	76.91 (9)	O14ⁱⁱⁱ—Na37—Na36ⁱⁱⁱ	49.99 (6)
O15ⁱⁱ—Na35—C27ⁱⁱⁱ	118.90 (9)	O14ⁱⁱⁱ—Na37—Na36ⁱⁱ	107.83 (7)
O15ⁱⁱ—Na35—O28ⁱⁱⁱ	149.41 (9)	O15—Na37—N1ⁱⁱⁱ	112.82 (9)
O15ⁱⁱ—Na35—O29	91.21 (9)	O15—Na37—C2ⁱⁱⁱ	88.02 (10)
O15ⁱⁱ—Na35—O30ⁱⁱⁱ	96.73 (9)	O15—Na37—C12	22.25 (8)
O15ⁱⁱ—Na35—Na36ⁱⁱ	71.54 (7)	O15—Na37—O13	67.13 (8)
O15ⁱⁱ—Na35—Na36	81.21 (7)	O15—Na37—Na35ⁱⁱ	29.41 (6)
O15ⁱⁱ—Na35—Na37ⁱⁱ	30.87 (6)	O15—Na37—Na35^v	127.04 (7)
O15ⁱⁱ—Na35—Na37^v	69.18 (6)	O15—Na37—Na36ⁱⁱ	70.01 (6)
N16—Na35—C17	25.48 (9)	O15—Na37—Na36ⁱⁱⁱ	126.03 (7)
N16—Na35—C27ⁱⁱⁱ	112.70 (9)	O30ⁱⁱ—Na37—N1ⁱⁱⁱ	82.82 (9)
N16—Na35—Na36	118.67 (7)	O30ⁱⁱ—Na37—C2ⁱⁱⁱ	77.73 (10)
N16—Na35—Na36ⁱⁱ	153.86 (7)	O30ⁱⁱ—Na37—C12	118.21 (9)
N16—Na35—Na37^v	118.11 (7)	O30ⁱⁱ—Na37—O13	149.27 (9)
N16—Na35—Na37ⁱⁱ	74.45 (6)	O30ⁱⁱ—Na37—O14ⁱⁱⁱ	92.27 (9)
C17—Na35—Na36	139.79 (8)	O30ⁱⁱ—Na37—O15	95.96 (9)
C17—Na35—Na36ⁱⁱ	139.08 (8)	O30ⁱⁱ—Na37—Na35^v	31.26 (6)
C17—Na35—Na37^v	93.29 (7)	O30ⁱⁱ—Na37—Na35ⁱⁱ	68.97 (6)
C17—Na35—Na37ⁱⁱ	82.69 (7)	O30ⁱⁱ—Na37—Na36ⁱⁱ	70.37 (7)
C27ⁱⁱⁱ—Na35—C17	93.22 (9)	O30ⁱⁱ—Na37—Na36ⁱⁱⁱ	80.69 (6)
C27ⁱⁱⁱ—Na35—Na36	126.95 (7)	O33—Na37—N1ⁱⁱⁱ	158.05 (10)
C27ⁱⁱⁱ—Na35—Na36ⁱⁱ	80.24 (7)	O33—Na37—C2ⁱⁱⁱ	176.10 (11)
C27ⁱⁱⁱ—Na35—Na37ⁱⁱ	149.63 (7)	O33—Na37—C12	83.95 (9)
C27ⁱⁱⁱ—Na35—Na37^v	51.11 (6)	O33—Na37—O13	102.63 (9)
O28ⁱⁱⁱ—Na35—N16	80.90 (8)	O33—Na37—O14ⁱⁱⁱ	84.70 (9)
O28ⁱⁱⁱ—Na35—C17	76.96 (9)	O33—Na37—O15	88.11 (9)
O28ⁱⁱⁱ—Na35—C27ⁱⁱⁱ	47.57 (7)	O33—Na37—O30ⁱⁱ	102.21 (10)
O28ⁱⁱⁱ—Na35—Na36ⁱⁱ	121.72 (6)	O33—Na37—Na35ⁱⁱ	82.97 (7)
O28ⁱⁱⁱ—Na35—Na36	129.36 (7)	O33—Na37—Na35^v	97.80 (7)
O28ⁱⁱⁱ—Na35—Na37ⁱⁱ	154.89 (7)	O33—Na37—Na36ⁱⁱ	39.11 (7)
O28ⁱⁱⁱ—Na35—Na37^v	96.80 (6)	O33—Na37—Na36ⁱⁱⁱ	41.96 (6)
O29—Na35—N16	72.98 (8)	Na35^v—Na37—Na35ⁱⁱ	98.91 (4)
O29—Na35—C17	98.04 (9)	Na36ⁱⁱⁱ—Na37—Na35ⁱⁱ	108.19 (4)
O29—Na35—C27ⁱⁱⁱ	149.60 (9)	Na36ⁱⁱ—Na37—Na35^v	82.16 (3)
O29—Na35—O28ⁱⁱⁱ	107.95 (8)	Na36ⁱⁱⁱ—Na37—Na35^v	61.53 (3)
O29—Na35—O30ⁱⁱⁱ	170.97 (10)	Na36ⁱⁱ—Na37—Na35ⁱⁱ	50.77 (3)
O29—Na35—Na36	48.92 (6)	Na36ⁱⁱⁱ—Na37—Na36ⁱⁱ	58.08 (4)

N1—C2—C3—C4	0.9 (7)	C27ⁱⁱⁱ—Na35—Na36—Na35ⁱⁱ	−46.01 (9)
N1—C6—C10—C9	−178.4 (3)	C27ⁱⁱⁱ—Na35—Na36—Na36ⁱⁱ	−46.01 (9)
N1—C6—C10—C11	2.9 (5)	C27ⁱⁱⁱ—Na35—Na36—Na36^iv	−155.26 (9)
C2—N1—C6—C5	−1.1 (5)	C27ⁱⁱⁱ—Na35—Na36—Na37ⁱ	77.9 (3)
C2—N1—C6—C10	177.9 (3)	O28—C26—C27—O29	−118.7 (3)
C2—C3—C4—C5	−0.3 (7)	O28—C26—C27—O30	55.8 (4)
C3—C4—C5—C6	−0.9 (6)	O28—C26—C27—Na35ⁱ	21.5 (3)
C3—C4—C5—C7	−179.3 (4)	O28ⁱⁱⁱ—Na35—Na36—O14	−29.13 (13)
C4—C5—C6—N1	1.7 (5)	O28ⁱⁱⁱ—Na35—Na36—O29	79.27 (11)
C4—C5—C6—C10	−177.3 (3)	O28ⁱⁱⁱ—Na35—Na36—C32ⁱⁱ	−159.81 (10)
C4—C5—C7—C8	177.2 (4)	O28ⁱⁱⁱ—Na35—Na36—O33ⁱⁱ	174.69 (9)
C5—C6—C10—C9	0.6 (5)	O28ⁱⁱⁱ—Na35—Na36—O33ⁱ	86.89 (14)
C5—C6—C10—C11	−178.1 (3)	O28ⁱⁱⁱ—Na35—Na36—O34	−58.92 (13)
C5—C7—C8—C9	−0.5 (5)	O28ⁱⁱⁱ—Na35—Na36—O34ⁱⁱ	−134.32 (9)
C6—N1—C2—C3	−0.2 (6)	O28ⁱⁱⁱ—Na35—Na36—Na35ⁱⁱ	−107.65 (9)
C6—N1—C2—Na37ⁱ	113.2 (3)	O28ⁱⁱⁱ—Na35—Na36—Na36ⁱⁱ	−107.65 (9)
C6—C5—C7—C8	−1.1 (5)	O28ⁱⁱⁱ—Na35—Na36—Na36^iv	143.10 (9)
C6—C10—C11—C12	28.7 (5)	O28ⁱⁱⁱ—Na35—Na36—Na37ⁱ	16.3 (3)
C6—C10—C11—O13	−155.2 (3)	O29—C27—O30—Na35ⁱ	121.9 (3)
C7—C5—C6—N1	−179.9 (3)	O29—C27—O30—Na37ⁱⁱ	−32.8 (4)
C7—C5—C6—C10	1.1 (5)	O29—Na35—Na36—O14	−108.40 (12)
C7—C8—C9—C10	2.3 (5)	O29—Na35—Na36—C32ⁱⁱ	120.92 (11)
C8—C9—C10—C6	−2.4 (5)	O29—Na35—Na36—O33ⁱ	7.62 (14)
C8—C9—C10—C11	176.4 (3)	O29—Na35—Na36—O33ⁱⁱ	95.43 (10)
C9—C10—C11—C12	−150.0 (3)	O29—Na35—Na36—O34ⁱⁱ	146.41 (10)
C9—C10—C11—O13	26.1 (4)	O29—Na35—Na36—O34	−138.19 (14)
C10—C11—C12—O14	58.0 (4)	O29—Na35—Na36—Na35ⁱⁱ	173.08 (10)
C10—C11—C12—O15	−127.3 (3)	O29—Na35—Na36—Na36ⁱⁱ	173.08 (10)
C10—C11—C12—Na37	−161.5 (3)	O29—Na35—Na36—Na36^iv	63.83 (10)
C10—C11—O13—Na37	157.1 (2)	O29—Na35—Na36—Na37ⁱ	−63.0 (2)
C11—C12—O14—Na36	148.1 (2)	O30—C27—O29—Na35	84.3 (4)
C11—C12—O14—Na37ⁱ	−102.7 (3)	O30—C27—O29—Na36	−27.7 (4)
C11—C12—O15—Na35ⁱⁱ	153.0 (2)	O30ⁱⁱⁱ—Na35—Na36—O14	60.53 (13)
C11—C12—O15—Na37	−50.6 (3)	O30ⁱⁱⁱ—Na35—Na36—O29	168.92 (13)
C11—C12—Na37—N1ⁱⁱⁱ	40.10 (18)	O30ⁱⁱⁱ—Na35—Na36—C32ⁱⁱ	−70.16 (11)
C11—C12—Na37—C2ⁱⁱⁱ	56.71 (18)	O30ⁱⁱⁱ—Na35—Na36—O33ⁱ	176.54 (14)
C11—C12—Na37—O13	−11.98 (15)	O30ⁱⁱⁱ—Na35—Na36—O33ⁱⁱ	−95.65 (11)
C11—C12—Na37—O14ⁱⁱⁱ	−56.1 (2)	O30ⁱⁱⁱ—Na35—Na36—O34ⁱⁱ	−44.66 (11)
C11—C12—Na37—O15	134.9 (3)	O30ⁱⁱⁱ—Na35—Na36—O34	30.74 (13)
C11—C12—Na37—O30ⁱⁱ	134.19 (17)	O30ⁱⁱⁱ—Na35—Na36—Na35ⁱⁱ	−17.99 (10)
C11—C12—Na37—O33	−125.17 (18)	O30ⁱⁱⁱ—Na35—Na36—Na36^iv	−127.25 (10)
C11—C12—Na37—Na35ⁱⁱ	148.96 (19)	O30ⁱⁱⁱ—Na35—Na36—Na36ⁱⁱ	−17.99 (10)
C11—C12—Na37—Na35^v	139.73 (16)	O30ⁱⁱⁱ—Na35—Na36—Na37ⁱ	105.9 (2)
C11—C12—Na37—Na36ⁱⁱⁱ	−126.51 (16)	C31—C32—O33—Na36ⁱⁱ	175.8 (3)
C11—C12—Na37—Na36ⁱⁱ	−164.50 (17)	C31—C32—O33—Na36ⁱⁱⁱ	−85.1 (4)
C11—O13—Na37—N1ⁱⁱⁱ	−117.1 (2)	C31—C32—O33—Na37	61.6 (4)
C11—O13—Na37—C2ⁱⁱⁱ	−91.2 (2)	C31—C32—O34—Na35	71.9 (4)
C11—O13—Na37—C12	15.48 (19)	C31—C32—O34—Na36	−77.5 (4)
C11—O13—Na37—O14ⁱⁱⁱ	173.4 (2)	C31—C32—O34—Na36ⁱⁱ	−175.9 (3)
C11—O13—Na37—O15	2.5 (2)	C32—O33—Na37—N1ⁱⁱⁱ	−114.8 (3)
C11—O13—Na37—O30ⁱⁱ	−58.2 (3)	C32—O33—Na37—C12	26.4 (3)
C11—O13—Na37—O33	85.0 (2)	C32—O33—Na37—O13	−17.8 (3)
C11—O13—Na37—Na35ⁱⁱ	0.8 (2)	C32—O33—Na37—O14ⁱⁱⁱ	−124.8 (3)
C11—O13—Na37—Na35^v	−128.4 (2)	C32—O33—Na37—O15	48.3 (3)
C11—O13—Na37—Na36ⁱⁱ	47.9 (2)	C32—O33—Na37—O30ⁱⁱ	144.0 (3)
C11—O13—Na37—Na36ⁱⁱⁱ	121.2 (2)	C32—O33—Na37—Na35ⁱⁱ	77.3 (3)
C12—C11—O13—Na37	−26.6 (3)	C32—O33—Na37—Na35^v	175.4 (3)
C12—O14—Na36—O29	−125.1 (2)	C32—O33—Na37—Na36ⁱⁱ	108.2 (3)
C12—O14—Na36—C32ⁱⁱ	53.2 (3)	C32—O33—Na37—Na36ⁱⁱⁱ	−155.2 (3)
C12—O14—Na36—O33ⁱ	151.2 (2)	C32—O34—Na35—O15ⁱⁱ	144.5 (3)
C12—O14—Na36—O33ⁱⁱ	78.3 (3)	C32—O34—Na35—N16	−112.2 (3)
C12—O14—Na36—O34ⁱⁱ	35.8 (2)	C32—O34—Na35—C27ⁱⁱⁱ	26.1 (3)
C12—O14—Na36—O34	−49.5 (2)	C32—O34—Na35—O28ⁱⁱⁱ	−18.6 (3)
C12—O14—Na36—Na35ⁱⁱ	40.6 (2)	C32—O34—Na35—O29	−125.8 (3)
C12—O14—Na36—Na35	−68.7 (3)	C32—O34—Na35—O30ⁱⁱⁱ	47.6 (3)
C12—O14—Na36—Na36ⁱⁱ	−4.2 (2)	C32—O34—Na35—Na36ⁱⁱ	107.3 (3)
C12—O14—Na36—Na36^iv	118.4 (2)	C32—O34—Na35—Na36	−156.1 (3)
C12—O14—Na36—Na37ⁱ	124.8 (3)	C32—O34—Na35—Na37ⁱⁱ	175.7 (3)
C12—O15—Na37—N1ⁱⁱⁱ	94.6 (2)	C32—O34—Na35—Na37^v	77.4 (3)
C12—O15—Na37—C2ⁱⁱⁱ	101.9 (2)	C32—O34—Na36—O14	0.2 (3)
C12—O15—Na37—O13	26.0 (2)	C32—O34—Na36—O29	129.4 (3)
C12—O15—Na37—O30ⁱⁱ	179.3 (2)	C32—O34—Na36—C32ⁱⁱ	−117.5 (3)
C12—O15—Na37—O33	−78.6 (2)	C32—O34—Na36—O33ⁱⁱ	−139.0 (3)
C12—O15—Na37—Na35ⁱⁱ	−157.6 (3)	C32—O34—Na36—O33ⁱ	61.5 (4)
C12—O15—Na37—Na35^v	−176.94 (18)	C32—O34—Na36—O34ⁱⁱ	−97.5 (3)
C12—O15—Na37—Na36ⁱⁱⁱ	−97.9 (2)	C32—O34—Na36—Na35	157.3 (3)
C12—O15—Na37—Na36ⁱⁱ	−114.1 (2)	C32—O34—Na36—Na35ⁱⁱ	−62.9 (3)
O13—C11—C12—O14	−118.2 (3)	C32—O34—Na36—Na36^iv	−151.4 (3)
O13—C11—C12—O15	56.5 (4)	C32—O34—Na36—Na36ⁱⁱ	−97.5 (3)
O13—C11—C12—Na37	22.3 (3)	C32—O34—Na36—Na37ⁱ	−5.2 (3)
O14—C12—O15—Na35ⁱⁱ	−33.0 (4)	O33—C32—O34—Na35	−109.0 (3)
O14—C12—O15—Na37	123.3 (3)	O33—C32—O34—Na36ⁱⁱ	3.2 (3)
O14—C12—Na37—N1ⁱⁱⁱ	162.1 (3)	O33—C32—O34—Na36	101.6 (3)
O14—C12—Na37—C2ⁱⁱⁱ	178.7 (3)	O34—C32—O33—Na36ⁱⁱⁱ	95.9 (4)
O14—C12—Na37—O13	110.0 (3)	O34—C32—O33—Na36ⁱⁱ	−3.3 (3)
O14—C12—Na37—O14ⁱⁱⁱ	65.9 (4)	O34—C32—O33—Na37	−117.5 (3)
O14—C12—Na37—O15	−103.0 (4)	O34—Na35—Na36—O14	29.79 (12)
O14—C12—Na37—O30ⁱⁱ	−103.8 (3)	O34—Na35—Na36—O29	138.19 (14)
O14—C12—Na37—O33	−3.1 (3)	O34—Na35—Na36—C32ⁱⁱ	−100.89 (12)
O14—C12—Na37—Na35^v	−98.2 (3)	O34—Na35—Na36—O33ⁱ	145.81 (17)
O14—C12—Na37—Na35ⁱⁱ	−89.0 (3)	O34—Na35—Na36—O33ⁱⁱ	−126.39 (12)
O14—C12—Na37—Na36ⁱⁱⁱ	−4.5 (4)	O34—Na35—Na36—O34ⁱⁱ	−75.40 (13)
O14—C12—Na37—Na36ⁱⁱ	−42.5 (3)	O34—Na35—Na36—Na35ⁱⁱ	−48.73 (10)
O15—C12—O14—Na36	−25.8 (4)	O34—Na35—Na36—Na36ⁱⁱ	−48.73 (10)
O15—C12—O14—Na37ⁱ	83.5 (4)	O34—Na35—Na36—Na36^iv	−157.98 (13)
O15—C12—Na37—N1ⁱⁱⁱ	−94.8 (2)	O34—Na35—Na36—Na37ⁱ	75.2 (2)
O15—C12—Na37—C2ⁱⁱⁱ	−78.2 (2)	Na35ⁱⁱ—O15—Na37—N1ⁱⁱⁱ	−107.78 (12)
O15—C12—Na37—O13	−146.9 (2)	Na35ⁱⁱ—O15—Na37—C2ⁱⁱⁱ	−100.52 (13)
O15—C12—Na37—O14ⁱⁱⁱ	168.9 (2)	Na35ⁱⁱ—O15—Na37—C12	157.6 (3)
O15—C12—Na37—O30ⁱⁱ	−0.8 (2)	Na35ⁱⁱ—O15—Na37—O13	−176.45 (14)
O15—C12—Na37—O33	99.9 (2)	Na35ⁱⁱ—O15—Na37—O30ⁱⁱ	−23.08 (13)
O15—C12—Na37—Na35^v	4.8 (3)	Na35ⁱⁱ—O15—Na37—O33	79.00 (13)
O15—C12—Na37—Na35ⁱⁱ	14.02 (18)	Na35ⁱⁱ—O15—Na37—Na35^v	−19.35 (15)
O15—C12—Na37—Na36ⁱⁱⁱ	98.5 (2)	Na35ⁱⁱ—O15—Na37—Na36ⁱⁱⁱ	59.73 (14)
O15—C12—Na37—Na36ⁱⁱ	60.6 (2)	Na35ⁱⁱ—O15—Na37—Na36ⁱⁱ	43.51 (10)
O15ⁱⁱ—Na35—Na36—O14	152.22 (10)	Na35—N16—C17—C18	−110.9 (4)
O15ⁱⁱ—Na35—Na36—O29	−99.39 (10)	Na35—N16—C21—C20	96.9 (3)
O15ⁱⁱ—Na35—Na36—C32ⁱⁱ	21.53 (9)	Na35—N16—C21—C25	−83.1 (3)
O15ⁱⁱ—Na35—Na36—O33ⁱⁱ	−3.96 (9)	Na35—C17—C18—C19	−79.3 (4)
O15ⁱⁱ—Na35—Na36—O33ⁱ	−91.77 (14)	Na35ⁱ—C27—O29—Na35	147.06 (19)
O15ⁱⁱ—Na35—Na36—O34	122.42 (13)	Na35ⁱ—C27—O29—Na36	35.1 (4)
O15ⁱⁱ—Na35—Na36—O34ⁱⁱ	47.02 (9)	Na35ⁱ—C27—O30—Na37ⁱⁱ	−154.8 (3)
O15ⁱⁱ—Na35—Na36—Na35ⁱⁱ	73.70 (7)	Na35—O29—Na36—O14	108.43 (10)
O15ⁱⁱ—Na35—Na36—Na36ⁱⁱ	73.70 (7)	Na35—O29—Na36—C32ⁱⁱ	−69.96 (10)
O15ⁱⁱ—Na35—Na36—Na36^iv	−35.56 (9)	Na35—O29—Na36—O33ⁱ	−174.67 (10)
O15ⁱⁱ—Na35—Na36—Na37ⁱ	−162.4 (2)	Na35—O29—Na36—O33ⁱⁱ	−88.83 (9)
N16—C17—C18—C19	0.7 (6)	Na35—O29—Na36—O34	26.83 (9)
N16—C17—Na35—O15ⁱⁱ	99.8 (2)	Na35—O29—Na36—O34ⁱⁱ	−46.33 (13)
N16—C17—Na35—C27ⁱⁱⁱ	−141.3 (2)	Na35—O29—Na36—Na35ⁱⁱ	−21.2 (3)
N16—C17—Na35—O28ⁱⁱⁱ	−96.2 (2)	Na35—O29—Na36—Na36ⁱⁱ	−6.72 (9)
N16—C17—Na35—O29	10.4 (2)	Na35—O29—Na36—Na36^iv	−129.06 (7)
N16—C17—Na35—O30ⁱⁱⁱ	−162.8 (2)	Na35—O29—Na36—Na37ⁱ	164.97 (7)
N16—C17—Na35—Na36	41.0 (2)	Na35—O34—Na36—O14	−157.08 (9)
N16—C17—Na35—Na36ⁱⁱ	139.93 (17)	Na35—O34—Na36—O29	−27.94 (9)
N16—C17—Na35—Na37^v	167.53 (19)	Na35—O34—Na36—C32ⁱⁱ	85.13 (10)
N16—C17—Na35—Na37ⁱⁱ	68.96 (19)	Na35—O34—Na36—O33ⁱ	−95.8 (3)
N16—C21—C25—C24	−179.4 (3)	Na35—O34—Na36—O33ⁱⁱ	63.71 (12)
N16—C21—C25—C26	1.9 (4)	Na35—O34—Na36—O34ⁱⁱ	105.16 (11)
N16—Na35—Na36—O14	−131.57 (11)	Na35—O34—Na36—Na35ⁱⁱ	139.77 (8)
N16—Na35—Na36—O29	−23.17 (10)	Na35—O34—Na36—Na36^iv	51.3 (3)
N16—Na35—Na36—C32ⁱⁱ	97.75 (10)	Na35—O34—Na36—Na36ⁱⁱ	105.16 (11)
N16—Na35—Na36—O33ⁱ	−15.55 (15)	Na35—O34—Na36—Na37ⁱ	−162.53 (7)
N16—Na35—Na36—O33ⁱⁱ	72.25 (10)	Na36—O29—Na35—O15ⁱⁱ	77.22 (9)
N16—Na35—Na36—O34ⁱⁱ	123.24 (9)	Na36—O29—Na35—N16	158.84 (9)
N16—Na35—Na36—O34	−161.36 (13)	Na36—O29—Na35—C17	154.17 (9)
N16—Na35—Na36—Na35ⁱⁱ	149.91 (8)	Na36—O29—Na35—C27ⁱⁱⁱ	−95.16 (17)
N16—Na35—Na36—Na36ⁱⁱ	149.91 (8)	Na36—O29—Na35—O28ⁱⁱⁱ	−127.01 (8)
N16—Na35—Na36—Na36^iv	40.66 (10)	Na36—O29—Na35—O34	−26.85 (9)
N16—Na35—Na36—Na37ⁱ	−86.2 (2)	Na36—O29—Na35—Na36ⁱⁱ	6.24 (9)
C17—N16—C21—C20	−1.3 (5)	Na36—O29—Na35—Na37^v	38.65 (19)
C17—N16—C21—C25	178.6 (3)	Na36—O29—Na35—Na37ⁱⁱ	77.37 (6)
C17—N16—Na35—O15ⁱⁱ	−75.6 (2)	Na36ⁱⁱ—C32—O33—Na36ⁱⁱⁱ	99.1 (3)
C17—N16—Na35—C27ⁱⁱⁱ	42.6 (2)	Na36ⁱⁱ—C32—O33—Na37	−114.2 (2)
C17—N16—Na35—O28ⁱⁱⁱ	78.7 (2)	Na36ⁱⁱ—C32—O34—Na35	−112.2 (3)
C17—N16—Na35—O29	−169.2 (2)	Na36ⁱⁱ—C32—O34—Na36	98.4 (2)
C17—N16—Na35—O30ⁱⁱⁱ	18.6 (2)	Na36ⁱⁱ—O33—Na37—N1ⁱⁱⁱ	137.0 (2)
C17—N16—Na35—O34	176.7 (3)	Na36ⁱⁱⁱ—O33—Na37—N1ⁱⁱⁱ	40.5 (3)
C17—N16—Na35—Na36	−151.13 (18)	Na36ⁱⁱⁱ—O33—Na37—C12	−178.38 (11)
C17—N16—Na35—Na36ⁱⁱ	−73.2 (3)	Na36ⁱⁱ—O33—Na37—C12	−81.81 (10)
C17—N16—Na35—Na37ⁱⁱ	−106.1 (2)	Na36ⁱⁱⁱ—O33—Na37—O13	137.47 (9)
C17—N16—Na35—Na37^v	−14.1 (2)	Na36ⁱⁱ—O33—Na37—O13	−125.95 (9)
C17—C18—C19—C20	1.1 (6)	Na36ⁱⁱ—O33—Na37—O14ⁱⁱⁱ	126.98 (10)
C17—Na35—Na36—O14	−150.33 (13)	Na36ⁱⁱⁱ—O33—Na37—O14ⁱⁱⁱ	30.41 (10)
C17—Na35—Na36—O29	−41.94 (14)	Na36ⁱⁱ—O33—Na37—O15	−59.89 (10)
C17—Na35—Na36—C32ⁱⁱ	78.98 (14)	Na36ⁱⁱⁱ—O33—Na37—O15	−156.47 (10)
C17—Na35—Na36—O33ⁱ	−34.32 (18)	Na36ⁱⁱ—O33—Na37—O30ⁱⁱ	35.80 (11)
C17—Na35—Na36—O33ⁱⁱ	53.49 (14)	Na36ⁱⁱⁱ—O33—Na37—O30ⁱⁱ	−60.78 (11)
C17—Na35—Na36—O34	179.87 (16)	Na36ⁱⁱ—O33—Na37—Na35^v	67.25 (9)
C17—Na35—Na36—O34ⁱⁱ	104.48 (13)	Na36ⁱⁱⁱ—O33—Na37—Na35ⁱⁱ	−127.41 (9)
C17—Na35—Na36—Na35ⁱⁱ	131.15 (12)	Na36ⁱⁱⁱ—O33—Na37—Na35^v	−29.33 (10)
C17—Na35—Na36—Na36^iv	21.89 (15)	Na36ⁱⁱ—O33—Na37—Na35ⁱⁱ	−30.84 (8)
C17—Na35—Na36—Na36ⁱⁱ	131.15 (12)	Na36ⁱⁱ—O33—Na37—Na36ⁱⁱⁱ	96.57 (12)
C17—Na35—Na36—Na37ⁱ	−104.9 (2)	Na36ⁱⁱⁱ—O33—Na37—Na36ⁱⁱ	−96.57 (12)
C18—C17—Na35—O15ⁱⁱ	−143.4 (3)	Na36—O34—Na35—O15ⁱⁱ	−59.34 (11)
C18—C17—Na35—N16	116.8 (4)	Na36ⁱⁱ—O34—Na35—O15ⁱⁱ	37.24 (11)
C18—C17—Na35—C27ⁱⁱⁱ	−24.5 (3)	Na36ⁱⁱ—O34—Na35—N16	140.5 (2)
C18—C17—Na35—O28ⁱⁱⁱ	20.6 (3)	Na36—O34—Na35—N16	43.9 (3)
C18—C17—Na35—O29	127.2 (3)	Na36ⁱⁱ—O34—Na35—C27ⁱⁱⁱ	−81.24 (9)
C18—C17—Na35—O30ⁱⁱⁱ	−46.0 (3)	Na36—O34—Na35—C27ⁱⁱⁱ	−177.82 (10)
C18—C17—Na35—Na36ⁱⁱ	−103.3 (3)	Na36—O34—Na35—O28ⁱⁱⁱ	137.48 (9)
C18—C17—Na35—Na36	157.8 (2)	Na36ⁱⁱ—O34—Na35—O28ⁱⁱⁱ	−125.94 (9)
C18—C17—Na35—Na37ⁱⁱ	−174.2 (3)	Na36ⁱⁱ—O34—Na35—O29	126.94 (10)
C18—C17—Na35—Na37^v	−75.7 (3)	Na36—O34—Na35—O29	30.36 (10)
C18—C19—C20—C21	−2.8 (6)	Na36—O34—Na35—O30ⁱⁱⁱ	−156.29 (10)
C18—C19—C20—C22	178.7 (4)	Na36ⁱⁱ—O34—Na35—O30ⁱⁱⁱ	−59.70 (10)
C19—C20—C21—N16	3.0 (5)	Na36—O34—Na35—Na36ⁱⁱ	−96.58 (11)
C19—C20—C21—C25	−177.0 (3)	Na36ⁱⁱ—O34—Na35—Na36	96.58 (11)
C19—C20—C22—C23	176.9 (4)	Na36ⁱⁱ—O34—Na35—Na37^v	−29.93 (7)
C20—C21—C25—C24	0.5 (5)	Na36—O34—Na35—Na37^v	−126.51 (8)
C20—C21—C25—C26	−178.2 (3)	Na36—O34—Na35—Na37ⁱⁱ	−28.20 (9)
C20—C22—C23—C24	−0.6 (5)	Na36ⁱⁱ—O34—Na35—Na37ⁱⁱ	68.38 (8)
C21—N16—C17—C18	−0.6 (5)	Na36ⁱⁱ—O34—Na36—O14	97.76 (8)
C21—N16—C17—Na35	110.4 (3)	Na36ⁱⁱ—O34—Na36—O29	−133.10 (9)
C21—N16—Na35—O15ⁱⁱ	165.5 (2)	Na36ⁱⁱ—O34—Na36—C32ⁱⁱ	−20.03 (9)
C21—N16—Na35—C17	−118.9 (3)	Na36ⁱⁱ—O34—Na36—O33ⁱ	159.0 (2)
C21—N16—Na35—C27ⁱⁱⁱ	−76.3 (2)	Na36ⁱⁱ—O34—Na36—O33ⁱⁱ	−41.45 (10)
C21—N16—Na35—O28ⁱⁱⁱ	−40.1 (2)	Na36ⁱⁱ—O34—Na36—O34ⁱⁱ	0.0
C21—N16—Na35—O29	71.9 (2)	Na36ⁱⁱ—O34—Na36—Na35ⁱⁱ	34.61 (6)
C21—N16—Na35—O30ⁱⁱⁱ	−100.3 (2)	Na36ⁱⁱ—O34—Na36—Na35	−105.16 (11)
C21—N16—Na35—O34	57.8 (3)	Na36ⁱⁱ—O34—Na36—Na36^iv	−53.9 (2)
C21—N16—Na35—Na36	90.0 (2)	Na36ⁱⁱ—O34—Na36—Na37ⁱ	92.31 (11)
C21—N16—Na35—Na36ⁱⁱ	167.92 (17)	Na36ⁱⁱ—Na35—Na36—O14	78.52 (9)
C21—N16—Na35—Na37^v	−133.04 (18)	Na36ⁱⁱ—Na35—Na36—O29	−173.08 (10)
C21—N16—Na35—Na37ⁱⁱ	135.0 (2)	Na36ⁱⁱ—Na35—Na36—C32ⁱⁱ	−52.16 (7)
C21—C20—C22—C23	−1.6 (5)	Na36ⁱⁱ—Na35—Na36—O33ⁱⁱ	−77.66 (7)
C21—C25—C26—C27	31.5 (4)	Na36ⁱⁱ—Na35—Na36—O33ⁱ	−165.47 (14)
C21—C25—C26—O28	−153.1 (3)	Na36ⁱⁱ—Na35—Na36—O34ⁱⁱ	−26.67 (5)
C22—C20—C21—N16	−178.4 (3)	Na36ⁱⁱ—Na35—Na36—O34	48.73 (10)
C22—C20—C21—C25	1.6 (5)	Na36ⁱⁱ—Na35—Na36—Na35ⁱⁱ	0.0
C22—C23—C24—C25	2.9 (5)	Na36ⁱⁱ—Na35—Na36—Na36^iv	−109.25 (8)
C23—C24—C25—C21	−2.8 (5)	Na36ⁱⁱ—Na35—Na36—Na37ⁱ	123.9 (2)
C23—C24—C25—C26	176.0 (3)	Na37ⁱ—N1—C2—C3	−113.3 (4)
C24—C25—C26—C27	−147.2 (3)	Na37ⁱ—N1—C6—C5	98.4 (3)
C24—C25—C26—O28	28.1 (4)	Na37ⁱ—N1—C6—C10	−82.6 (3)
C25—C26—C27—O29	56.8 (4)	Na37ⁱ—C2—C3—C4	−79.8 (5)
C25—C26—C27—O30	−128.7 (3)	Na37—C12—O14—Na36	38.1 (4)
C25—C26—C27—Na35ⁱ	−163.0 (3)	Na37—C12—O14—Na37ⁱ	147.35 (19)
C25—C26—O28—Na35ⁱ	159.2 (2)	Na37—C12—O15—Na35ⁱⁱ	−156.4 (3)
C26—C27—O29—Na35	−102.1 (3)	Na37ⁱ—O14—Na36—O29	110.11 (10)
C26—C27—O29—Na36	145.9 (2)	Na37ⁱ—O14—Na36—C32ⁱⁱ	−71.52 (11)
C26—C27—O30—Na35ⁱ	−51.8 (3)	Na37ⁱ—O14—Na36—O33ⁱ	26.48 (9)
C26—C27—O30—Na37ⁱⁱ	153.47 (19)	Na37ⁱ—O14—Na36—O33ⁱⁱ	−46.44 (14)
C27—C26—O28—Na35ⁱ	−25.2 (3)	Na37ⁱ—O14—Na36—O34	−174.25 (9)
C27—O29—Na35—O15ⁱⁱ	−54.6 (2)	Na37ⁱ—O14—Na36—O34ⁱⁱ	−88.98 (9)
C27—O29—Na35—N16	27.0 (2)	Na37ⁱ—O14—Na36—Na35ⁱⁱ	−84.20 (7)
C27—O29—Na35—C17	22.3 (2)	Na37ⁱ—O14—Na36—Na35	166.51 (7)
C27—O29—Na35—C27ⁱⁱⁱ	133.0 (3)	Na37ⁱ—O14—Na36—Na36^iv	−6.35 (9)
C27—O29—Na35—O28ⁱⁱⁱ	101.1 (2)	Na37ⁱ—O14—Na36—Na36ⁱⁱ	−128.95 (7)
C27—O29—Na35—O34	−158.7 (2)	Na37^v—Na35—Na36—O14	88.21 (9)
C27—O29—Na35—Na36ⁱⁱ	−125.6 (2)	Na37ⁱⁱ—Na35—Na36—O14	177.91 (9)
C27—O29—Na35—Na36	−131.9 (3)	Na37ⁱⁱ—Na35—Na36—O29	−73.69 (8)
C27—O29—Na35—Na37^v	−93.2 (3)	Na37^v—Na35—Na36—O29	−163.40 (9)
C27—O29—Na35—Na37ⁱⁱ	−54.5 (2)	Na37^v—Na35—Na36—C32ⁱⁱ	−42.48 (8)
C27—O29—Na36—O14	−124.9 (2)	Na37ⁱⁱ—Na35—Na36—C32ⁱⁱ	47.23 (7)
C27—O29—Na36—C32ⁱⁱ	56.7 (3)	Na37^v—Na35—Na36—O33ⁱⁱ	−67.97 (7)
C27—O29—Na36—O33ⁱ	−48.0 (2)	Na37ⁱⁱ—Na35—Na36—O33ⁱⁱ	21.73 (6)
C27—O29—Na36—O33ⁱⁱ	37.8 (2)	Na37ⁱⁱ—Na35—Na36—O33ⁱ	−66.07 (12)
C27—O29—Na36—O34	153.5 (2)	Na37^v—Na35—Na36—O33ⁱ	−155.78 (12)
C27—O29—Na36—O34ⁱⁱ	80.3 (3)	Na37ⁱⁱ—Na35—Na36—O34ⁱⁱ	72.72 (6)
C27—O29—Na36—Na35	126.7 (3)	Na37^v—Na35—Na36—O34ⁱⁱ	−16.98 (7)
C27—O29—Na36—Na35ⁱⁱ	105.5 (3)	Na37ⁱⁱ—Na35—Na36—O34	148.12 (11)
C27—O29—Na36—Na36^iv	−2.4 (2)	Na37^v—Na35—Na36—O34	58.42 (11)
C27—O29—Na36—Na36ⁱⁱ	120.0 (2)	Na37^v—Na35—Na36—Na35ⁱⁱ	9.69 (5)
C27—O29—Na36—Na37ⁱ	−68.4 (3)	Na37ⁱⁱ—Na35—Na36—Na35ⁱⁱ	99.39 (5)
C27ⁱⁱⁱ—Na35—Na36—O14	32.51 (13)	Na37ⁱⁱ—Na35—Na36—Na36^iv	−9.86 (6)
C27ⁱⁱⁱ—Na35—Na36—O29	140.91 (12)	Na37^v—Na35—Na36—Na36^iv	−99.57 (7)
C27ⁱⁱⁱ—Na35—Na36—C32ⁱⁱ	−98.17 (11)	Na37ⁱⁱ—Na35—Na36—Na36ⁱⁱ	99.39 (5)
C27ⁱⁱⁱ—Na35—Na36—O33ⁱ	148.52 (14)	Na37^v—Na35—Na36—Na36ⁱⁱ	9.69 (5)
C27ⁱⁱⁱ—Na35—Na36—O33ⁱⁱ	−123.67 (10)	Na37^v—Na35—Na36—Na37ⁱ	133.6 (2)
C27ⁱⁱⁱ—Na35—Na36—O34ⁱⁱ	−72.68 (10)	Na37ⁱⁱ—Na35—Na36—Na37ⁱ	−136.7 (2)
C27ⁱⁱⁱ—Na35—Na36—O34	2.72 (13)

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

Experimental details

Crystal data
Chemical formula	[Na₃(C₁₁H₆NO₃)₂(C₂H₃O₂)]
M_r	528.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.1101 (5), 22.7075 (19), 16.1587 (12)
β (°)	94.626 (7)
V (Å³)	2234.6 (3)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.50
Crystal size (mm)	0.19 × 0.04 × 0.03

Data collection
Diffractometer	Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction	Analytical [CrysAlis PRO (Agilent, 2014), based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.887, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	7799, 3943, 2557
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.130, 0.99
No. of reflections	3943
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.29

Computer programs: CrysAlis PRO (Agilent, 2014), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010).

Acknowledgements

The authors wish to thank the University of Leeds for a University Research Scholarship (RLN) and funding.

References

Agilent (2014). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887–897. CrossRef CAS Web of Science IUCr Journals Google Scholar
Crespo-Peña, A., Monge, D., Martín-Zamora, E., Álvarez, E., Fernández, R. & Lassaletta, J. M. (2012). J. Am. Chem. Soc. 134, 12912–12915. PubMed Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 11| November 2014| Pages m385-m386

doi:10.1107/S1600536814023423

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of poly[μ-acetato-bis­­[μ-2-oxo-2-(quinolin-8-yl)ethano­ato]tris­­odium]

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Crystal structure of poly[μ-acetato-bis[μ-2-oxo-2-(quinolin-8-yl)ethanoato]trisodium]