Tetra-μ-benzoato-bis-{[4-(pyrrolidin-1-yl)pyridine]zinc(II)}.

The central part of the title centrosymmetric dinuclear complex, [Zn(2)(C(7)H(5)O(2))(4)(C(9)H(12)N(2))(2)], has a paddle-wheel conformation with four benzoate ligands bridging two symmetry-related Zn(II) ions. The distorted square-pyramidal coordination environment around the Zn(II) ion is completed by an N atom from a 4-(pyrrolidin-1-yl)pyridine ligand. The Zn⋯Zn separation of 2.9826 (12) Å does not represent a formal direct metal-metal bond. The Zn(II) ion is displaced by 0.381 (1) Å from the mean plane of the four basal O atoms. Two of the C atoms of the pyrrolidine ring are disordered over two sites with refined occupancies of 0.53 (2) and 0.47 (2).

Related literature

For crystal structures containing the [Zn2(O2CPh)4] unit, see: Necefoglu et al. (2002 ▶); Zeleňák et al. (2004 ▶); Karmakar et al. (2006 ▶); Ohmura et al. (2005 ▶). For the crystal structures of copper(II) and zinc(II) benzoates with quinoxaline, 6-methyl­quinoline, 3-methyl­quinoline, di-2-pyridyl ketone and trans-1-(2-pyrid­yl)-2-(4-pyrid­yl)ethyl­ene, see: Lee et al. (2008 ▶); Yu et al. (2008 ▶, 2009 ▶); Park et al. (2008 ▶); Shin et al. (2009 ▶); Song et al. (2009 ▶). For transition metal ions as the major cation contributors to the inorganic composition of natural water and biological fluids, see: Daniele et al. (2008 ▶); Parkin (2004 ▶); Tshuva & Lippard (2004 ▶).

Experimental

Crystal data

[Zn2(C7H5O2)4(C9H12N2)2]

M = 911.59

Monoclinic,

a = 11.0021 (11) Å

b = 11.4303 (11) Å

c = 16.9508 (16) Å

β = 93.869 (2)°

V = 2126.8 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.19 mm−1

T = 293 K

0.08 × 0.08 × 0.01 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.909, T max = 0.988

11271 measured reflections

4159 independent reflections

2284 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.179

S = 0.90

4159 reflections

270 parameters

7 restraints

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.71 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052714/lh2962sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052714/lh2962Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Zn2(C7H5O2)4(C9H12N2)2]	F(000) = 944
Mr = 911.59	Dx = 1.423 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1481 reflections
a = 11.0021 (11) Å	θ = 2.3–19.2°
b = 11.4303 (11) Å	µ = 1.19 mm−1
c = 16.9508 (16) Å	T = 293 K
β = 93.869 (2)°	Plate, colorless
V = 2126.8 (4) Å3	0.08 × 0.08 × 0.01 mm
Z = 2

Bruker SMART CCD diffractometer	4159 independent reflections
Radiation source: fine-focus sealed tube	2284 reflections with I > 2σ(I)
graphite	Rint = 0.068
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.909, Tmax = 0.988	k = −13→14
11271 measured reflections	l = −17→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179	H-atom parameters constrained
S = 0.90	w = 1/[σ2(Fo2) + (0.1079P)2] where P = (Fo2 + 2Fc2)/3
4159 reflections	(Δ/σ)max < 0.001
270 parameters	Δρmax = 0.94 e Å−3
7 restraints	Δρmin = −0.71 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Zn1	0.11885 (5)	0.44449 (5)	0.02560 (4)	0.0380 (2)
O11	0.1576 (4)	0.5331 (3)	−0.0760 (2)	0.0524 (11)
O12	0.0192 (4)	0.3879 (4)	0.1160 (2)	0.0574 (11)
O21	0.1591 (3)	0.5941 (3)	0.0872 (2)	0.0528 (10)
O22	0.0201 (4)	0.3274 (3)	−0.0446 (2)	0.0562 (11)
N31	0.2720 (4)	0.3488 (4)	0.0436 (2)	0.0389 (10)
N32	0.5772 (4)	0.1339 (4)	0.0637 (3)	0.0494 (12)
C11	0.0949 (5)	0.5977 (5)	−0.1189 (3)	0.0409 (13)
C12	0.1545 (5)	0.6638 (4)	−0.1822 (3)	0.0428 (14)
C13	0.2792 (6)	0.6570 (5)	−0.1882 (3)	0.0556 (16)
H13	0.3250	0.6061	−0.1554	0.067*
C14	0.3364 (7)	0.7242 (6)	−0.2419 (4)	0.072 (2)
H14	0.4207	0.7224	−0.2436	0.086*
C15	0.2653 (9)	0.7955 (7)	−0.2942 (5)	0.089 (3)
H15	0.3025	0.8385	−0.3325	0.107*
C16	0.1429 (8)	0.8024 (6)	−0.2898 (4)	0.074 (2)
H16	0.0974	0.8523	−0.3236	0.089*
C17	0.0854 (6)	0.7365 (5)	−0.2356 (3)	0.0542 (15)
H17	0.0011	0.7397	−0.2342	0.065*
C21	0.0822 (6)	0.6758 (5)	0.0839 (3)	0.0444 (14)
C22	0.1148 (5)	0.7854 (4)	0.1296 (3)	0.0384 (13)
C23	0.0408 (6)	0.8808 (5)	0.1229 (4)	0.0638 (18)
H23	−0.0297	0.8774	0.0894	0.077*
C24	0.0676 (7)	0.9824 (6)	0.1645 (5)	0.084 (3)
H24	0.0174	1.0476	0.1580	0.101*
C25	0.1670 (8)	0.9853 (6)	0.2142 (5)	0.082 (2)
H25	0.1835	1.0527	0.2438	0.098*
C26	0.2463 (7)	0.8915 (6)	0.2234 (4)	0.0710 (19)
H26	0.3159	0.8950	0.2576	0.085*
C27	0.2173 (6)	0.7926 (5)	0.1794 (4)	0.0579 (17)
H27	0.2695	0.7286	0.1838	0.069*
C31	0.3724 (5)	0.3727 (5)	0.0069 (3)	0.0455 (14)
H31	0.3719	0.4391	−0.0249	0.055*
C32	0.4768 (5)	0.3064 (5)	0.0126 (4)	0.0531 (16)
H32	0.5441	0.3287	−0.0142	0.064*
C33	0.4810 (5)	0.2046 (5)	0.0591 (3)	0.0422 (13)
C34	0.3747 (5)	0.1802 (5)	0.0984 (4)	0.0517 (16)
H34	0.3719	0.1152	0.1312	0.062*
C35	0.2759 (5)	0.2528 (5)	0.0879 (3)	0.0478 (15)
H35	0.2066	0.2335	0.1136	0.057*
C36	0.6859 (5)	0.1549 (5)	0.0198 (4)	0.0573 (17)
H36A	0.7297	0.2235	0.0398	0.069*	0.47 (2)
H36B	0.6639	0.1656	−0.0361	0.069*	0.47 (2)
C37	0.7631 (14)	0.0439 (11)	0.0341 (9)	0.054 (4)*	0.47 (2)
H37A	0.7416	−0.0159	−0.0050	0.065*	0.47 (2)
H37B	0.8495	0.0607	0.0340	0.065*	0.47 (2)
C38	0.7273 (7)	0.008 (2)	0.1161 (9)	0.067 (6)*	0.47 (2)
H38A	0.7685	0.0566	0.1567	0.080*	0.47 (2)
H38B	0.7467	−0.0731	0.1268	0.080*	0.47 (2)
C39	0.5882 (5)	0.0289 (5)	0.1122 (4)	0.0607 (18)
H39A	0.5441	−0.0362	0.0872	0.073*	0.47 (2)
H39B	0.5595	0.0420	0.1643	0.073*	0.47 (2)
H36C	0.7113	0.2360	0.0238	0.069*	0.53 (2)
H36D	0.6710	0.1345	−0.0355	0.069*	0.53 (2)
C37A	0.7824 (9)	0.0733 (12)	0.0611 (11)	0.073 (5)*	0.53 (2)
H37C	0.8362	0.0425	0.0231	0.088*	0.53 (2)
H37D	0.8310	0.1156	0.1016	0.088*	0.53 (2)
C38A	0.7126 (9)	−0.0257 (12)	0.0979 (11)	0.063 (5)*	0.53 (2)
H38C	0.7539	−0.0514	0.1473	0.076*	0.53 (2)
H38D	0.7034	−0.0919	0.0622	0.076*	0.53 (2)
H39C	0.5231	−0.0254	0.0971	0.073*	0.53 (2)
H39D	0.5839	0.0486	0.1676	0.073*	0.53 (2)

	U11	U22	U33	U12	U13	U23
Zn1	0.0382 (4)	0.0339 (3)	0.0421 (4)	0.0065 (3)	0.0043 (3)	0.0011 (3)
O11	0.061 (3)	0.051 (2)	0.047 (2)	0.011 (2)	0.011 (2)	0.017 (2)
O12	0.055 (3)	0.064 (3)	0.056 (3)	0.007 (2)	0.016 (2)	0.016 (2)
O21	0.052 (3)	0.040 (2)	0.064 (3)	0.007 (2)	−0.011 (2)	−0.010 (2)
O22	0.054 (3)	0.050 (2)	0.063 (3)	−0.002 (2)	−0.010 (2)	−0.014 (2)
N31	0.038 (3)	0.038 (2)	0.041 (3)	0.005 (2)	0.002 (2)	0.005 (2)
N32	0.043 (3)	0.052 (3)	0.053 (3)	0.016 (2)	0.006 (2)	0.010 (2)
C11	0.055 (4)	0.034 (3)	0.035 (3)	−0.005 (3)	0.012 (3)	−0.003 (2)
C12	0.053 (4)	0.037 (3)	0.039 (3)	−0.004 (3)	0.012 (3)	−0.004 (3)
C13	0.063 (4)	0.061 (4)	0.044 (3)	−0.008 (3)	0.013 (3)	−0.005 (3)
C14	0.073 (5)	0.076 (5)	0.068 (5)	−0.023 (4)	0.027 (4)	−0.015 (4)
C15	0.135 (8)	0.071 (5)	0.066 (5)	−0.035 (5)	0.046 (6)	0.000 (4)
C16	0.109 (7)	0.066 (5)	0.046 (4)	−0.005 (4)	0.004 (4)	0.018 (3)
C17	0.063 (4)	0.051 (4)	0.048 (4)	−0.004 (3)	−0.001 (3)	0.008 (3)
C21	0.062 (4)	0.035 (3)	0.037 (3)	−0.002 (3)	0.017 (3)	0.004 (2)
C22	0.037 (3)	0.041 (3)	0.037 (3)	−0.007 (2)	0.005 (3)	−0.005 (2)
C23	0.047 (4)	0.049 (4)	0.096 (5)	0.006 (3)	0.003 (4)	−0.018 (4)
C24	0.062 (5)	0.060 (5)	0.128 (7)	0.012 (4)	−0.026 (5)	−0.038 (5)
C25	0.103 (7)	0.052 (4)	0.093 (6)	−0.013 (4)	0.022 (5)	−0.028 (4)
C26	0.083 (5)	0.068 (5)	0.059 (4)	−0.015 (4)	−0.016 (4)	−0.013 (4)
C27	0.080 (5)	0.038 (3)	0.054 (4)	0.000 (3)	0.000 (4)	0.002 (3)
C31	0.040 (3)	0.046 (3)	0.050 (3)	0.003 (3)	0.001 (3)	0.015 (3)
C32	0.048 (4)	0.055 (4)	0.058 (4)	0.004 (3)	0.016 (3)	0.012 (3)
C33	0.042 (3)	0.041 (3)	0.044 (3)	0.009 (3)	0.001 (3)	−0.001 (3)
C34	0.053 (4)	0.043 (3)	0.061 (4)	0.011 (3)	0.012 (3)	0.017 (3)
C35	0.043 (3)	0.043 (3)	0.059 (4)	0.005 (3)	0.016 (3)	0.011 (3)
C36	0.047 (4)	0.064 (4)	0.062 (4)	0.015 (3)	0.013 (3)	0.006 (3)
C39	0.061 (4)	0.050 (4)	0.072 (4)	0.017 (3)	0.006 (4)	0.009 (3)
C36A	0.047 (4)	0.064 (4)	0.062 (4)	0.015 (3)	0.013 (3)	0.006 (3)
C39A	0.061 (4)	0.050 (4)	0.072 (4)	0.017 (3)	0.006 (4)	0.009 (3)

Zn1—N31	2.014 (4)	C23—H23	0.9300
Zn1—O21	2.036 (4)	C24—C25	1.335 (11)
Zn1—O12	2.048 (4)	C24—H24	0.9300
Zn1—O22	2.053 (4)	C25—C26	1.384 (11)
Zn1—O11	2.068 (4)	C25—H25	0.9300
Zn1—Zn1i	2.9826 (12)	C26—C27	1.380 (8)
O11—C11	1.216 (6)	C26—H26	0.9300
O12—C11i	1.270 (6)	C27—H27	0.9300
O21—C21	1.260 (6)	C31—C32	1.374 (7)
O22—C21i	1.268 (7)	C31—H31	0.9300
N31—C35	1.329 (6)	C32—C33	1.404 (7)
N31—C31	1.333 (6)	C32—H32	0.9300
N32—C33	1.330 (6)	C33—C34	1.412 (7)
N32—C39	1.454 (7)	C34—C35	1.370 (7)
N32—C36	1.470 (7)	C34—H34	0.9300
C11—O12i	1.270 (6)	C35—H35	0.9300
C11—C12	1.500 (7)	C36—C37	1.536 (7)
C12—C13	1.384 (8)	C36—H36A	0.9700
C12—C17	1.413 (8)	C36—H36B	0.9700
C13—C14	1.375 (8)	C37—C38	1.525 (10)
C13—H13	0.9300	C37—H37A	0.9700
C14—C15	1.403 (11)	C37—H37B	0.9700
C14—H14	0.9300	C38—C39	1.545 (7)
C15—C16	1.356 (10)	C38—H38A	0.9700
C15—H15	0.9300	C38—H38B	0.9700
C16—C17	1.374 (8)	C39—H39A	0.9700
C16—H16	0.9300	C39—H39B	0.9700
C17—H17	0.9300	C37A—C38A	1.524 (10)
C21—O22i	1.268 (7)	C37A—H37C	0.9700
C21—C22	1.504 (7)	C37A—H37D	0.9700
C22—C23	1.361 (8)	C38A—H38C	0.9700
C22—C27	1.364 (8)	C38A—H38D	0.9700
C23—C24	1.380 (9)
N31—Zn1—O21	103.14 (17)	C25—C24—H24	120.6
N31—Zn1—O12	101.53 (16)	C23—C24—H24	120.6
O21—Zn1—O12	89.46 (17)	C24—C25—C26	122.3 (7)
N31—Zn1—O22	97.95 (17)	C24—C25—H25	118.9
O21—Zn1—O22	158.90 (16)	C26—C25—H25	118.9
O12—Zn1—O22	86.50 (17)	C27—C26—C25	117.0 (7)
N31—Zn1—O11	100.06 (16)	C27—C26—H26	121.5
O21—Zn1—O11	88.04 (16)	C25—C26—H26	121.5
O12—Zn1—O11	158.27 (16)	C22—C27—C26	122.3 (6)
O22—Zn1—O11	88.11 (16)	C22—C27—H27	118.8
N31—Zn1—Zn1i	169.40 (13)	C26—C27—H27	118.8
O21—Zn1—Zn1i	87.02 (11)	N31—C31—C32	124.7 (5)
O12—Zn1—Zn1i	81.31 (12)	N31—C31—H31	117.7
O22—Zn1—Zn1i	71.90 (12)	C32—C31—H31	117.7
O11—Zn1—Zn1i	77.01 (12)	C31—C32—C33	119.5 (5)
C11—O11—Zn1	130.8 (4)	C31—C32—H32	120.2
C11i—O12—Zn1	124.6 (4)	C33—C32—H32	120.2
C21—O21—Zn1	118.5 (4)	N32—C33—C32	122.2 (5)
C21i—O22—Zn1	137.7 (4)	N32—C33—C34	122.2 (5)
C35—N31—C31	115.9 (4)	C32—C33—C34	115.6 (5)
C35—N31—Zn1	122.0 (3)	C35—C34—C33	119.6 (5)
C31—N31—Zn1	122.0 (4)	C35—C34—H34	120.2
C33—N32—C39	124.8 (4)	C33—C34—H34	120.2
C33—N32—C36	122.8 (5)	N31—C35—C34	124.7 (5)
C39—N32—C36	112.4 (4)	N31—C35—H35	117.6
O11—C11—O12i	125.3 (5)	C34—C35—H35	117.6
O11—C11—C12	118.4 (5)	N32—C36—C37	104.2 (6)
O12i—C11—C12	116.3 (5)	N32—C36—H36A	110.9
C13—C12—C17	118.6 (5)	C37—C36—H36A	110.9
C13—C12—C11	120.5 (6)	N32—C36—H36B	110.9
C17—C12—C11	120.8 (5)	C37—C36—H36B	110.9
C14—C13—C12	121.2 (7)	H36A—C36—H36B	108.9
C14—C13—H13	119.4	C38—C37—C36	100.9 (9)
C12—C13—H13	119.4	C38—C37—H37A	111.6
C13—C14—C15	118.8 (7)	C36—C37—H37A	111.6
C13—C14—H14	120.6	C38—C37—H37B	111.6
C15—C14—H14	120.6	C36—C37—H37B	111.6
C16—C15—C14	120.8 (6)	H37A—C37—H37B	109.4
C16—C15—H15	119.6	C37—C38—C39	103.7 (8)
C14—C15—H15	119.6	C37—C38—H38A	111.0
C15—C16—C17	120.6 (7)	C39—C38—H38A	111.0
C15—C16—H16	119.7	C37—C38—H38B	111.0
C17—C16—H16	119.7	C39—C38—H38B	111.0
C16—C17—C12	119.9 (6)	H38A—C38—H38B	109.0
C16—C17—H17	120.0	N32—C39—C38	101.2 (8)
C12—C17—H17	120.0	N32—C39—H39A	111.5
O21—C21—O22i	124.9 (5)	C38—C39—H39A	111.5
O21—C21—C22	117.3 (6)	N32—C39—H39B	111.5
O22i—C21—C22	117.9 (5)	C38—C39—H39B	111.5
C23—C22—C27	118.0 (5)	H39A—C39—H39B	109.3
C23—C22—C21	120.2 (5)	C38A—C37A—H37C	110.4
C27—C22—C21	121.8 (5)	C38A—C37A—H37D	110.4
C22—C23—C24	121.6 (7)	H37C—C37A—H37D	108.6
C22—C23—H23	119.2	C37A—C38A—H38C	111.0
C24—C23—H23	119.2	C37A—C38A—H38D	111.0
C25—C24—C23	118.8 (7)	H38C—C38A—H38D	109.0
N31—Zn1—O11—C11	173.5 (5)	C14—C15—C16—C17	−2.3 (11)
O21—Zn1—O11—C11	−83.5 (5)	C15—C16—C17—C12	2.2 (10)
O12—Zn1—O11—C11	0.1 (8)	C13—C12—C17—C16	−2.8 (9)
O22—Zn1—O11—C11	75.8 (5)	C11—C12—C17—C16	175.6 (5)
Zn1i—Zn1—O11—C11	3.9 (5)	Zn1—O21—C21—O22i	0.0 (7)
N31—Zn1—O12—C11i	−162.7 (4)	Zn1—O21—C21—C22	−179.7 (3)
O21—Zn1—O12—C11i	94.0 (5)	O21—C21—C22—C23	174.1 (5)
O22—Zn1—O12—C11i	−65.2 (5)	O22i—C21—C22—C23	−5.6 (7)
O11—Zn1—O12—C11i	10.7 (8)	O21—C21—C22—C27	−6.7 (7)
Zn1i—Zn1—O12—C11i	7.0 (4)	O22i—C21—C22—C27	173.6 (5)
N31—Zn1—O21—C21	176.1 (4)	C27—C22—C23—C24	0.3 (9)
O12—Zn1—O21—C21	−82.2 (4)	C21—C22—C23—C24	179.5 (6)
O22—Zn1—O21—C21	−3.3 (7)	C22—C23—C24—C25	−2.0 (12)
O11—Zn1—O21—C21	76.2 (4)	C23—C24—C25—C26	2.4 (13)
Zn1i—Zn1—O21—C21	−0.8 (4)	C24—C25—C26—C27	−1.0 (12)
N31—Zn1—O22—C21i	−175.1 (5)	C23—C22—C27—C26	1.1 (9)
O21—Zn1—O22—C21i	4.4 (8)	C21—C22—C27—C26	−178.1 (5)
O12—Zn1—O22—C21i	83.8 (5)	C25—C26—C27—C22	−0.8 (10)
O11—Zn1—O22—C21i	−75.2 (5)	C35—N31—C31—C32	−0.5 (9)
Zn1i—Zn1—O22—C21i	1.8 (5)	Zn1—N31—C31—C32	−175.5 (5)
O21—Zn1—N31—C35	110.2 (4)	N31—C31—C32—C33	0.8 (10)
O12—Zn1—N31—C35	18.1 (5)	C39—N32—C33—C32	178.5 (6)
O22—Zn1—N31—C35	−70.0 (4)	C36—N32—C33—C32	−1.1 (9)
O11—Zn1—N31—C35	−159.4 (4)	C39—N32—C33—C34	−3.7 (9)
Zn1i—Zn1—N31—C35	−86.5 (8)	C36—N32—C33—C34	176.7 (6)
O21—Zn1—N31—C31	−75.2 (5)	C31—C32—C33—N32	176.6 (6)
O12—Zn1—N31—C31	−167.3 (4)	C31—C32—C33—C34	−1.3 (9)
O22—Zn1—N31—C31	104.7 (4)	N32—C33—C34—C35	−176.4 (6)
O11—Zn1—N31—C31	15.2 (5)	C32—C33—C34—C35	1.6 (9)
Zn1i—Zn1—N31—C31	88.1 (8)	C31—N31—C35—C34	0.8 (9)
Zn1—O11—C11—O12i	−10.9 (9)	Zn1—N31—C35—C34	175.8 (5)
Zn1—O11—C11—C12	171.0 (3)	C33—C34—C35—N31	−1.4 (10)
O11—C11—C12—C13	−4.1 (8)	C33—N32—C36—C37	−172.3 (9)
O12i—C11—C12—C13	177.6 (5)	C39—N32—C36—C37	8.1 (10)
O11—C11—C12—C17	177.5 (5)	N32—C36—C37—C38	−30.5 (16)
O12i—C11—C12—C17	−0.7 (7)	C36—C37—C38—C39	42 (2)
C17—C12—C13—C14	3.6 (9)	C33—N32—C39—C38	−162.0 (9)
C11—C12—C13—C14	−174.8 (5)	C36—N32—C39—C38	17.6 (10)
C12—C13—C14—C15	−3.6 (9)	C37—C38—C39—N32	−36.8 (17)
C13—C14—C15—C16	3.0 (11)