Bis(μ-2-{bis-[(2-oxidobenzyl-idene)amino]-meth-yl}phenolato)bis-[(tetra-hydro-furan)-samarium(III)] tetra-hydro-furan disolvate.

In the centrosymmetric binuclear complex of the title solvate, [Sm(2)(C(21)H(15)N(2)O(3))(2)(C(4)H(8)O)(2)]·2C(4)H(8)O, the Sm(III) is coordin-ated in a distorted monocapped octa-hedral geometry by four O atoms and two N atoms from two tridentate deprotonated 2-{bis-[(2-oxidobenzyl-idene)amino]-meth-yl}phenolate ligands and an O atom of a tetra-hydro-furan (THF) mol-ecule. The Sm⋯Sm distance in the complex is 3.8057 (4) Å. Parts of the coordinating THF mol-ecule are disordered over two sets of sites in a 0.56 (3):0.44 (3) ratio. The complex and solvent mol-ecules are linked into a three-dimensional structure via C-H⋯O hydrogen-bonding inter-actions.

Related literature

For general reports on the tripodal ligand 2-bis-(salicyl­idiene­­amino)­methyl­phenol, see: Nabulsi et al. (1988 ▶); Achim et al. (2001 ▶); Yu et al. (1991 ▶); Snyder et al.(1989 ▶); Chaudhuri et al. (1998 ▶); Illingsworth et al. (2002 ▶). For related structures, see: Howell et al. (1998 ▶); Liu et al. (1998 ▶); Dubé et al. (1998 ▶). For ionic radii, see: Shannon (1976 ▶).

Experimental

Crystal data

[Sm2(C21H15N2O3)2(C4H8O)2]·2C4H8O

M = 1275.84

Monoclinic,

a = 11.7184 (11) Å

b = 21.378 (2) Å

c = 11.1464 (11) Å

β = 99.058 (1)°

V = 2757.5 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.17 mm−1

T = 293 K

0.23 × 0.18 × 0.16 mm

Data collection

Rigaku Rapid I CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.635, T max = 0.723

23697 measured reflections

6291 independent reflections

5362 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.01

6291 reflections

353 parameters

42 restraints

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.49 e Å−3

Data collection: CrystalClear (Rigaku, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: publCIF (Westrip, 2010 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015759/wm2610sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015759/wm2610Isup2.hkl

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

[Sm2(C21H15N2O3)2(C4H8O)2]·2C4H8O	F(000) = 1284
Mr = 1275.84	Dx = 1.537 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6291 reflections
a = 11.7184 (11) Å	θ = 1.8–27.5°
b = 21.378 (2) Å	µ = 2.17 mm−1
c = 11.1464 (11) Å	T = 293 K
β = 99.058 (1)°	Prism, yellow
V = 2757.5 (5) Å3	0.23 × 0.18 × 0.16 mm
Z = 2

Rigaku Rapid I CCD diffractometer	6291 independent reflections
Radiation source: fine-focus sealed tube	5362 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
phi and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→15
Tmin = 0.635, Tmax = 0.723	k = −27→27
23697 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0311P)2 + 2.4255P] where P = (Fo2 + 2Fc2)/3
6291 reflections	(Δ/σ)max = 0.001
353 parameters	Δρmax = 0.62 e Å−3
42 restraints	Δρmin = −0.49 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)
Sm1	0.633331 (14)	0.050642 (8)	0.045466 (14)	0.03765 (7)
O1	0.4566 (2)	0.04480 (10)	−0.0885 (2)	0.0399 (5)
N1	0.4689 (2)	0.08291 (12)	0.1669 (2)	0.0368 (6)
C1	0.4042 (3)	0.10064 (16)	−0.1113 (3)	0.0415 (7)
O2	0.7114 (2)	0.05416 (12)	0.2385 (2)	0.0510 (6)
N2	0.2865 (2)	0.03847 (12)	0.0800 (2)	0.0376 (6)
C2	0.4009 (4)	0.1298 (2)	−0.2238 (3)	0.0587 (10)
H2B	0.4309	0.1096	−0.2858	0.070*
O3	0.2239 (2)	−0.08830 (12)	0.0432 (3)	0.0640 (8)
C3	0.3533 (4)	0.1885 (2)	−0.2430 (5)	0.0777 (14)
H3A	0.3516	0.2075	−0.3182	0.093*
C4	0.3082 (4)	0.2194 (2)	−0.1527 (5)	0.0732 (13)
H4A	0.2778	0.2595	−0.1660	0.088*
O5	0.1336 (5)	0.3502 (3)	−0.1746 (6)	0.1290 (16)
C5	0.3088 (3)	0.19034 (17)	−0.0424 (4)	0.0570 (10)
H5A	0.2766	0.2109	0.0178	0.068*
C6	0.3561 (3)	0.13107 (16)	−0.0184 (3)	0.0425 (7)
C7	0.3516 (3)	0.09823 (15)	0.0998 (3)	0.0401 (7)
H7A	0.3123	0.1254	0.1511	0.048*
C8	0.6870 (3)	0.05687 (15)	0.3492 (3)	0.0461 (8)
C9	0.7750 (4)	0.0467 (2)	0.4482 (4)	0.0656 (12)
H9A	0.8493	0.0377	0.4336	0.079*
C10	0.7542 (5)	0.0496 (2)	0.5665 (4)	0.0794 (15)
H10A	0.8145	0.0427	0.6301	0.095*
C11	0.6450 (5)	0.0626 (2)	0.5916 (4)	0.0789 (15)
H11A	0.6309	0.0646	0.6713	0.095*
C12	0.5580 (4)	0.0726 (2)	0.4966 (3)	0.0645 (11)
H12A	0.4843	0.0811	0.5133	0.077*
C13	0.5755 (3)	0.07050 (17)	0.3742 (3)	0.0454 (8)
C14	0.4763 (3)	0.08349 (16)	0.2826 (3)	0.0443 (8)
H14A	0.4087	0.0937	0.3120	0.053*
C15	0.1322 (3)	−0.07402 (19)	0.0914 (3)	0.0505 (8)
C16	0.0517 (4)	−0.1210 (2)	0.1098 (4)	0.0672 (12)
H16A	0.0643	−0.1620	0.0876	0.081*
C17	−0.0452 (4)	−0.1066 (2)	0.1603 (4)	0.0672 (12)
H17A	−0.0966	−0.1383	0.1721	0.081*
C18	−0.0673 (3)	−0.0468 (2)	0.1935 (4)	0.0619 (11)
H18A	−0.1333	−0.0377	0.2269	0.074*
C19	0.0096 (3)	−0.0006 (2)	0.1764 (3)	0.0517 (9)
H19A	−0.0054	0.0402	0.1984	0.062*
C20	0.1104 (3)	−0.01278 (17)	0.1268 (3)	0.0425 (7)
C21	0.1904 (3)	0.03821 (16)	0.1224 (3)	0.0419 (7)
H21A	0.1698	0.0759	0.1546	0.050*
O4	0.6278 (2)	0.17034 (12)	0.0626 (2)	0.0548 (7)
C22	0.6431 (5)	0.2121 (2)	−0.0357 (4)	0.0754 (14)
H22A	0.5697	0.2300	−0.0723	0.091*
H22B	0.6767	0.1902	−0.0978	0.091*
C23	0.7226 (16)	0.2615 (7)	0.0220 (11)	0.079 (4)	0.56 (3)
H23A	0.8018	0.2524	0.0127	0.094*	0.56 (3)
H23B	0.7014	0.3021	−0.0137	0.094*	0.56 (3)
C23'	0.647 (3)	0.2738 (6)	0.0115 (14)	0.088 (6)	0.44 (3)
H23C	0.5731	0.2945	−0.0144	0.106*	0.44 (3)
H23D	0.7064	0.2977	−0.0188	0.106*	0.44 (3)
C24	0.709 (3)	0.2603 (12)	0.146 (2)	0.138 (10)	0.56 (3)
H24A	0.6689	0.2977	0.1659	0.166*	0.56 (3)
H24B	0.7842	0.2595	0.1970	0.166*	0.56 (3)
C24'	0.671 (3)	0.2708 (12)	0.144 (3)	0.102 (8)	0.44 (3)
H24C	0.7510	0.2802	0.1741	0.122*	0.44 (3)
H24D	0.6220	0.2998	0.1803	0.122*	0.44 (3)
C25	0.6426 (6)	0.2047 (2)	0.1716 (5)	0.099 (2)
H25A	0.6848	0.1804	0.2377	0.119*
H25B	0.5685	0.2166	0.1930	0.119*
C26	0.1419 (11)	0.3737 (5)	−0.0552 (11)	0.182 (4)
H26A	0.1247	0.4181	−0.0561	0.219*
H26B	0.2189	0.3671	−0.0104	0.219*
C27	0.0526 (12)	0.3368 (7)	0.0020 (11)	0.210 (5)
H27A	0.0870	0.3019	0.0501	0.252*
H27B	0.0110	0.3632	0.0512	0.252*
C28	−0.0164 (13)	0.3174 (7)	−0.1032 (16)	0.234 (7)
H28A	−0.0423	0.2752	−0.0907	0.281*
H28B	−0.0844	0.3440	−0.1166	0.281*
C29	0.0337 (11)	0.3180 (5)	−0.2067 (13)	0.189 (5)
H29A	0.0490	0.2758	−0.2318	0.227*
H29B	−0.0159	0.3388	−0.2726	0.227*

	U11	U22	U33	U12	U13	U23
Sm1	0.04306 (11)	0.03983 (11)	0.03134 (10)	0.00188 (7)	0.00982 (7)	−0.00368 (6)
O1	0.0485 (13)	0.0387 (12)	0.0329 (12)	0.0053 (9)	0.0080 (10)	0.0013 (9)
N1	0.0417 (14)	0.0387 (14)	0.0301 (13)	0.0009 (11)	0.0057 (11)	−0.0049 (11)
C1	0.0417 (17)	0.0445 (18)	0.0359 (17)	−0.0001 (14)	−0.0015 (13)	0.0054 (14)
O2	0.0491 (14)	0.0656 (17)	0.0367 (13)	0.0100 (11)	0.0022 (11)	−0.0019 (11)
N2	0.0392 (14)	0.0422 (14)	0.0316 (14)	0.0018 (11)	0.0060 (11)	−0.0041 (11)
C2	0.069 (3)	0.063 (2)	0.042 (2)	0.002 (2)	0.0040 (18)	0.0136 (18)
O3	0.0641 (17)	0.0511 (15)	0.086 (2)	−0.0039 (13)	0.0419 (16)	−0.0080 (14)
C3	0.090 (3)	0.070 (3)	0.068 (3)	0.006 (3)	−0.005 (3)	0.032 (2)
C4	0.075 (3)	0.048 (2)	0.090 (4)	0.010 (2)	−0.005 (3)	0.022 (2)
O5	0.146 (4)	0.104 (3)	0.140 (4)	−0.003 (3)	0.031 (3)	0.027 (3)
C5	0.052 (2)	0.044 (2)	0.074 (3)	0.0074 (17)	0.0041 (19)	−0.0034 (18)
C6	0.0416 (18)	0.0374 (17)	0.0472 (19)	0.0013 (13)	0.0029 (14)	0.0009 (14)
C7	0.0438 (18)	0.0424 (17)	0.0342 (16)	0.0055 (14)	0.0067 (13)	−0.0074 (13)
C8	0.060 (2)	0.0399 (18)	0.0357 (18)	0.0019 (15)	−0.0008 (15)	−0.0005 (13)
C9	0.069 (3)	0.076 (3)	0.047 (2)	0.016 (2)	−0.007 (2)	0.0040 (19)
C10	0.100 (4)	0.092 (4)	0.038 (2)	0.015 (3)	−0.016 (2)	0.008 (2)
C11	0.109 (4)	0.094 (4)	0.031 (2)	0.002 (3)	0.004 (2)	0.007 (2)
C12	0.079 (3)	0.082 (3)	0.034 (2)	−0.002 (2)	0.0131 (19)	0.0017 (19)
C13	0.054 (2)	0.0492 (19)	0.0322 (17)	−0.0051 (16)	0.0049 (15)	0.0009 (14)
C14	0.0471 (19)	0.052 (2)	0.0350 (17)	−0.0029 (15)	0.0118 (14)	−0.0041 (15)
C15	0.048 (2)	0.059 (2)	0.046 (2)	−0.0026 (17)	0.0133 (16)	0.0009 (17)
C16	0.065 (3)	0.059 (2)	0.083 (3)	−0.012 (2)	0.028 (2)	−0.005 (2)
C17	0.047 (2)	0.084 (3)	0.072 (3)	−0.016 (2)	0.015 (2)	0.003 (2)
C18	0.038 (2)	0.098 (3)	0.051 (2)	−0.001 (2)	0.0095 (17)	0.006 (2)
C19	0.0440 (19)	0.071 (2)	0.0399 (19)	0.0075 (17)	0.0066 (15)	0.0024 (17)
C20	0.0377 (17)	0.061 (2)	0.0281 (16)	0.0022 (15)	0.0029 (13)	0.0010 (14)
C21	0.0444 (18)	0.0512 (19)	0.0305 (16)	0.0064 (14)	0.0067 (14)	−0.0026 (13)
O4	0.0740 (18)	0.0430 (14)	0.0503 (15)	−0.0026 (12)	0.0192 (13)	−0.0008 (11)
C22	0.117 (4)	0.054 (2)	0.057 (3)	−0.003 (3)	0.018 (3)	0.013 (2)
C23	0.083 (8)	0.075 (7)	0.081 (7)	−0.023 (6)	0.025 (7)	0.012 (5)
C23'	0.129 (17)	0.041 (6)	0.093 (9)	−0.019 (8)	0.010 (10)	0.004 (6)
C24	0.23 (2)	0.093 (15)	0.078 (11)	−0.082 (15)	−0.006 (13)	−0.015 (9)
C24'	0.20 (2)	0.040 (7)	0.082 (12)	−0.008 (10)	0.077 (14)	−0.004 (7)
C25	0.184 (7)	0.058 (3)	0.062 (3)	−0.022 (3)	0.038 (4)	−0.011 (2)
C26	0.216 (8)	0.150 (7)	0.170 (7)	−0.023 (6)	−0.001 (7)	−0.007 (6)
C27	0.209 (9)	0.256 (9)	0.175 (8)	0.040 (7)	0.066 (7)	0.020 (7)
C28	0.231 (10)	0.228 (10)	0.262 (10)	−0.026 (8)	0.096 (9)	−0.013 (8)
C29	0.175 (10)	0.126 (8)	0.259 (15)	0.000 (7)	0.013 (10)	0.013 (9)

Sm1—O2	2.203 (2)	C15—C20	1.402 (5)
Sm1—O3i	2.223 (3)	C15—C16	1.414 (5)
Sm1—O1	2.358 (2)	C16—C17	1.380 (6)
Sm1—O1i	2.380 (2)	C16—H16A	0.9300
Sm1—O4	2.568 (3)	C17—C18	1.365 (6)
Sm1—N1	2.616 (3)	C17—H17A	0.9300
Sm1—N2i	2.623 (3)	C18—C19	1.371 (6)
Sm1—Sm1i	3.8057 (4)	C18—H18A	0.9300
O1—C1	1.348 (4)	C19—C20	1.405 (5)
O1—Sm1i	2.380 (2)	C19—H19A	0.9300
N1—C14	1.279 (4)	C20—C21	1.443 (5)
N1—C7	1.494 (4)	C21—H21A	0.9300
C1—C2	1.396 (5)	O4—C25	1.407 (5)
C1—C6	1.413 (5)	O4—C22	1.446 (5)
O2—C8	1.312 (4)	C22—C23'	1.419 (14)
N2—C21	1.289 (4)	C22—C23	1.486 (12)
N2—C7	1.487 (4)	C22—H22A	0.9700
N2—Sm1i	2.623 (3)	C22—H22B	0.9700
C2—C3	1.375 (6)	C23—C24	1.42 (3)
C2—H2B	0.9300	C23—H23A	0.9700
O3—C15	1.310 (4)	C23—H23B	0.9700
O3—Sm1i	2.223 (3)	C23'—C24'	1.46 (3)
C3—C4	1.379 (7)	C23'—H23C	0.9700
C3—H3A	0.9300	C23'—H23D	0.9700
C4—C5	1.376 (6)	C24—C25	1.47 (3)
C4—H4A	0.9300	C24—H24A	0.9700
O5—C29	1.357 (11)	C24—H24B	0.9700
O5—C26	1.412 (11)	C24'—C25	1.49 (3)
C5—C6	1.392 (5)	C24'—H24C	0.9700
C5—H5A	0.9300	C24'—H24D	0.9700
C6—C7	1.501 (5)	C25—H25A	0.9700
C7—H7A	0.9800	C25—H25B	0.9700
C8—C9	1.403 (5)	C26—C27	1.527 (14)
C8—C13	1.409 (5)	C26—H26A	0.9700
C9—C10	1.380 (7)	C26—H26B	0.9700
C9—H9A	0.9300	C27—C28	1.379 (16)
C10—C11	1.381 (8)	C27—H27A	0.9700
C10—H10A	0.9300	C27—H27B	0.9700
C11—C12	1.365 (7)	C28—C29	1.374 (15)
C11—H11A	0.9300	C28—H28A	0.9700
C12—C13	1.412 (5)	C28—H28B	0.9700
C12—H12A	0.9300	C29—H29A	0.9700
C13—C14	1.447 (5)	C29—H29B	0.9700
C14—H14A	0.9300
O2—Sm1—O3i	101.30 (11)	C18—C17—C16	121.5 (4)
O2—Sm1—O1	143.97 (9)	C18—C17—H17A	119.2
O3i—Sm1—O1	112.64 (10)	C16—C17—H17A	119.2
O2—Sm1—O1i	87.80 (9)	C17—C18—C19	118.7 (4)
O3i—Sm1—O1i	142.00 (8)	C17—C18—H18A	120.7
O1—Sm1—O1i	73.11 (8)	C19—C18—H18A	120.7
O2—Sm1—O4	84.53 (9)	C18—C19—C20	122.2 (4)
O3i—Sm1—O4	72.66 (9)	C18—C19—H19A	118.9
O1—Sm1—O4	94.01 (8)	C20—C19—H19A	118.9
O1i—Sm1—O4	145.32 (8)	C15—C20—C19	119.0 (3)
O2—Sm1—N1	73.27 (9)	C15—C20—C21	123.2 (3)
O3i—Sm1—N1	143.28 (9)	C19—C20—C21	117.6 (3)
O1—Sm1—N1	72.33 (8)	N2—C21—C20	128.7 (3)
O1i—Sm1—N1	74.71 (8)	N2—C21—H21A	115.6
O4—Sm1—N1	70.69 (8)	C20—C21—H21A	115.6
O2—Sm1—N2i	114.64 (9)	C25—O4—C22	108.6 (3)
O3i—Sm1—N2i	70.63 (9)	C25—O4—Sm1	125.7 (3)
O1—Sm1—N2i	88.65 (8)	C22—O4—Sm1	123.5 (2)
O1i—Sm1—N2i	72.04 (8)	C23'—C22—O4	107.1 (7)
O4—Sm1—N2i	141.16 (8)	O4—C22—C23	104.8 (6)
N1—Sm1—N2i	145.30 (8)	C23'—C22—H22A	76.2
C1—O1—Sm1	113.65 (19)	O4—C22—H22A	110.8
C1—O1—Sm1i	126.4 (2)	C23—C22—H22A	110.8
Sm1—O1—Sm1i	106.89 (8)	C23'—C22—H22B	136.3
C14—N1—C7	114.4 (3)	O4—C22—H22B	110.8
C14—N1—Sm1	125.9 (2)	C23—C22—H22B	110.8
C7—N1—Sm1	119.56 (18)	H22A—C22—H22B	108.9
O1—C1—C2	120.8 (3)	C24—C23—C22	104.4 (11)
O1—C1—C6	119.5 (3)	C24—C23—H23A	110.9
C2—C1—C6	119.7 (3)	C22—C23—H23A	110.9
C8—O2—Sm1	143.3 (2)	C24—C23—H23B	110.9
C21—N2—C7	114.0 (3)	C22—C23—H23B	110.9
C21—N2—Sm1i	126.8 (2)	H23A—C23—H23B	108.9
C7—N2—Sm1i	119.02 (18)	C22—C23'—C24'	108.8 (13)
C3—C2—C1	120.0 (4)	C22—C23'—H23C	109.9
C3—C2—H2B	120.0	C24'—C23'—H23C	109.9
C1—C2—H2B	120.0	C22—C23'—H23D	109.9
C15—O3—Sm1i	145.1 (3)	C24'—C23'—H23D	109.9
C2—C3—C4	121.1 (4)	H23C—C23'—H23D	108.3
C2—C3—H3A	119.4	C23—C24—C25	110.3 (14)
C4—C3—H3A	119.4	C23—C24—H24A	109.6
C5—C4—C3	119.1 (4)	C25—C24—H24A	109.6
C5—C4—H4A	120.5	C23—C24—H24B	109.6
C3—C4—H4A	120.5	C25—C24—H24B	109.6
C29—O5—C26	110.9 (9)	H24A—C24—H24B	108.1
C4—C5—C6	122.0 (4)	C25—C24'—C23'	103.6 (18)
C4—C5—H5A	119.0	C25—C24'—H24C	111.0
C6—C5—H5A	119.0	C23'—C24'—H24C	111.0
C5—C6—C1	118.1 (3)	C25—C24'—H24D	111.0
C5—C6—C7	121.8 (3)	C23'—C24'—H24D	111.0
C1—C6—C7	120.1 (3)	H24C—C24'—H24D	109.0
N2—C7—N1	107.2 (2)	O4—C25—C24'	108.6 (11)
N2—C7—C6	111.1 (3)	O4—C25—C24	104.7 (10)
N1—C7—C6	112.7 (3)	O4—C25—H25A	110.8
N2—C7—H7A	108.6	C24'—C25—H25A	124.0
N1—C7—H7A	108.6	C24—C25—H25A	110.8
C6—C7—H7A	108.6	O4—C25—H25B	110.8
O2—C8—C9	119.4 (4)	C24'—C25—H25B	92.0
O2—C8—C13	122.8 (3)	C24—C25—H25B	110.8
C9—C8—C13	117.8 (4)	H25A—C25—H25B	108.9
C10—C9—C8	121.7 (5)	O5—C26—C27	105.1 (9)
C10—C9—H9A	119.1	O5—C26—H26A	110.7
C8—C9—H9A	119.1	C27—C26—H26A	110.7
C9—C10—C11	120.7 (4)	O5—C26—H26B	110.7
C9—C10—H10A	119.6	C27—C26—H26B	110.7
C11—C10—H10A	119.6	H26A—C26—H26B	108.8
C12—C11—C10	118.5 (4)	C28—C27—C26	98.6 (10)
C12—C11—H11A	120.7	C28—C27—H27A	112.1
C10—C11—H11A	120.7	C26—C27—H27A	112.1
C11—C12—C13	122.7 (4)	C28—C27—H27B	112.1
C11—C12—H12A	118.6	C26—C27—H27B	112.1
C13—C12—H12A	118.6	H27A—C27—H27B	109.7
C8—C13—C12	118.5 (4)	C29—C28—C27	116.1 (14)
C8—C13—C14	124.5 (3)	C29—C28—H28A	108.3
C12—C13—C14	117.0 (4)	C27—C28—H28A	108.3
N1—C14—C13	129.0 (3)	C29—C28—H28B	108.3
N1—C14—H14A	115.5	C27—C28—H28B	108.3
C13—C14—H14A	115.5	H28A—C28—H28B	107.4
O3—C15—C20	122.0 (3)	O5—C29—C28	104.4 (12)
O3—C15—C16	120.2 (4)	O5—C29—H29A	110.9
C20—C15—C16	117.8 (3)	C28—C29—H29A	110.9
C17—C16—C15	120.8 (4)	O5—C29—H29B	110.9
C17—C16—H16A	119.6	C28—C29—H29B	110.9
C15—C16—H16A	119.6	H29A—C29—H29B	108.9

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O5	0.93	2.56	3.450 (7)	159
C21—H21A···O5ii	0.93	2.56	3.424 (6)	155
C22—H22B···O3i	0.97	2.50	3.079 (6)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O5	0.93	2.56	3.450 (7)	159
C21—H21A⋯O5i	0.93	2.56	3.424 (6)	155
C22—H22B⋯O3ii	0.97	2.50	3.079 (6)	118

Symmetry codes: (i) ; (ii) .