catena-Poly[[[aqua-[3-(3-hy-droxy-phen-yl)prop-2-enoato]samarium(III)]-bis-[μ(2)-3-(3-hy-droxy-phen-yl)prop-2-enoato]] monohydrate].

The title Sm(III) compound, {[Sm(C(9)H(7)O(3))(3)(H(2)O)]·H(2)O}(n), was obtained under hydrothermal conditions. Its structure is isotypic with the analogous Eu complex. The latter was reported incorrectly in space group P1 by Yan et al. [J. Mol. Struct. (2008), 891, 298-304]. This was corrected by Marsh [Acta Cryst. B65, 782-783] to P-1. The Sm(III) ion is nine-coordinated by O atoms from one coordinating water molecule and the remaining ones from the 3-(3-hy-droxy-phen-yl)prop-2-enoatate anions (one bidentate, two bidentate and bridging, two monodentate bridging), leading to a distorted tricapped trigonal-prismatic coordination polyhedron surrounded by solvent water mol-ecules. In the crystal, extensive intermolecular O-H⋯O hydrogen-bonding inter-actions and π-π inter-actions [centroid-centroid separation = 3.9393 (1) Å] lead to the formation of a three-dimensional supra-molecular network.

Related literature

For the isotypic Eu structure, see: Yan et al. (2008 ▶) and for the corrected space-group assignment, see: Marsh (2009 ▶). For related structures, see: Niu et al. (2008 ▶); Tang et al. (2009 ▶); Wang & Feng (2010 ▶); Xue et al. (2007 ▶); Ye et al. (2005 ▶).

Experimental

Crystal data

[Sm(C9H7O3)3(H2O)]·H2O

M = 675.82

Triclinic,

a = 7.9411 (1) Å

b = 13.0312 (2) Å

c = 13.6564 (2) Å

α = 97.356 (1)°

β = 97.120 (1)°

γ = 103.739 (1)°

V = 1343.87 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.25 mm−1

T = 296 K

0.52 × 0.24 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.53, T max = 0.71

17958 measured reflections

4722 independent reflections

4590 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.037

S = 1.04

4722 reflections

373 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812013724/zj2052sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013724/zj2052Isup2.hkl

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

[Sm(C9H7O3)3(H2O)]·H2O	Z = 2
Mr = 675.82	F(000) = 674
Triclinic, P1	Dx = 1.670 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9411 (1) Å	Cell parameters from 9871 reflections
b = 13.0312 (2) Å	θ = 1.6–25.0°
c = 13.6564 (2) Å	µ = 2.25 mm−1
α = 97.356 (1)°	T = 296 K
β = 97.120 (1)°	Block, yellow
γ = 103.739 (1)°	0.52 × 0.24 × 0.15 mm
V = 1343.87 (3) Å3

Bruker APEXII area-detector diffractometer	4722 independent reflections
Radiation source: fine-focus sealed tube	4590 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.53, Tmax = 0.71	k = −15→15
17958 measured reflections	l = −16→16

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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.037	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0243P)2 + 0.3656P] where P = (Fo2 + 2Fc2)/3
4722 reflections	(Δ/σ)max = 0.002
373 parameters	Δρmax = 0.40 e Å−3
10 restraints	Δρmin = −0.47 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
Sm1	0.231707 (9)	0.462033 (5)	0.480253 (5)	0.01695 (4)
O1	0.06012 (15)	0.55519 (9)	0.59671 (8)	0.0240 (2)
O1W	0.07151 (18)	0.32289 (11)	0.56401 (11)	0.0324 (3)
H1WA	−0.034 (2)	0.318 (2)	0.5643 (17)	0.049*
H1WB	0.109 (3)	0.312 (2)	0.6205 (14)	0.049*
O2	0.32583 (16)	0.54888 (12)	0.65526 (9)	0.0349 (3)
O2W	0.7925 (2)	0.70266 (18)	0.25319 (14)	0.0629 (5)
H2WA	0.786 (4)	0.7600 (17)	0.232 (3)	0.094*
H2WB	0.697 (3)	0.661 (2)	0.232 (3)	0.094*
O3	0.4554 (2)	0.56809 (15)	1.19165 (12)	0.0515 (4)
H3	0.401 (3)	0.5246 (19)	1.2314 (18)	0.062*
O4	0.51185 (15)	0.59885 (9)	0.47391 (9)	0.0240 (3)
O5	0.26831 (15)	0.64608 (9)	0.43899 (10)	0.0278 (3)
O6	1.0331 (2)	1.09500 (12)	0.39523 (14)	0.0506 (4)
H6	1.080 (3)	1.1627 (15)	0.382 (2)	0.061*
O7	0.19076 (17)	0.29241 (9)	0.36232 (9)	0.0306 (3)
O8	0.28389 (16)	0.44152 (9)	0.30584 (9)	0.0259 (3)
O9	0.3333 (5)	0.1288 (2)	−0.16532 (17)	0.1181 (11)
H9	0.351 (6)	0.077 (3)	−0.215 (3)	0.142*
C1	0.3318 (3)	0.59470 (16)	1.12695 (14)	0.0358 (4)
C2	0.1850 (3)	0.62021 (18)	1.15591 (15)	0.0437 (5)
H2A	0.1672	0.6218	1.2221	0.052*
C3	0.0638 (3)	0.6435 (2)	1.08592 (16)	0.0479 (6)
H3A	−0.0346	0.6618	1.1056	0.057*
C4	0.0877 (3)	0.63986 (18)	0.98720 (15)	0.0401 (5)
H4A	0.0039	0.6541	0.9406	0.048*
C5	0.2359 (3)	0.61510 (15)	0.95721 (14)	0.0313 (4)
C6	0.3595 (3)	0.59493 (16)	1.02878 (14)	0.0349 (4)
H6A	0.4621	0.5814	1.0104	0.042*
C7	0.2629 (2)	0.60020 (16)	0.85277 (14)	0.0320 (4)
H7A	0.3726	0.5922	0.8417	0.038*
C8	0.1498 (2)	0.59684 (16)	0.77289 (13)	0.0306 (4)
H8A	0.0447	0.6140	0.7811	0.037*
C9	0.1830 (2)	0.56691 (14)	0.67091 (13)	0.0237 (4)
C10	0.8553 (3)	1.07639 (15)	0.38269 (15)	0.0351 (4)
C11	0.7683 (3)	1.14997 (15)	0.35253 (16)	0.0406 (5)
H11A	0.8315	1.2160	0.3411	0.049*
C12	0.5879 (3)	1.12497 (16)	0.33946 (18)	0.0457 (5)
H12A	0.5299	1.1749	0.3196	0.055*
C13	0.4906 (3)	1.02652 (16)	0.35534 (17)	0.0395 (5)
H13A	0.3686	1.0104	0.3454	0.047*
C14	0.5770 (3)	0.95222 (14)	0.38628 (14)	0.0305 (4)
C15	0.7603 (3)	0.97840 (14)	0.40027 (15)	0.0329 (4)
H15A	0.8194	0.9296	0.4216	0.040*
C16	0.4745 (3)	0.84864 (14)	0.40343 (14)	0.0306 (4)
H16A	0.3529	0.8359	0.3920	0.037*
C17	0.5399 (2)	0.77163 (14)	0.43369 (14)	0.0291 (4)
H17A	0.6614	0.7836	0.4458	0.035*
C18	0.4330 (2)	0.66875 (13)	0.44924 (12)	0.0214 (3)
C19	0.2960 (5)	0.0830 (2)	−0.0827 (2)	0.0676 (8)
C20	0.2780 (5)	−0.0240 (2)	−0.0819 (2)	0.0729 (9)
H20A	0.2905	−0.0681	−0.1383	0.087*
C21	0.2415 (5)	−0.0653 (2)	0.0023 (3)	0.0786 (10)
H21A	0.2308	−0.1377	0.0036	0.094*
C22	0.2202 (4)	−0.0002 (2)	0.0858 (2)	0.0643 (8)
H22A	0.1926	−0.0294	0.1422	0.077*
C23	0.2398 (3)	0.10820 (18)	0.08566 (17)	0.0436 (5)
C24	0.2779 (4)	0.1496 (2)	0.00018 (18)	0.0572 (7)
H24A	0.2912	0.2222	−0.0014	0.069*
C25	0.2225 (3)	0.17526 (16)	0.17687 (15)	0.0390 (5)
H25A	0.1776	0.1391	0.2262	0.047*
C26	0.2632 (3)	0.28090 (15)	0.19707 (14)	0.0319 (4)
H26A	0.3052	0.3196	0.1486	0.038*
C27	0.2452 (2)	0.34016 (14)	0.29289 (13)	0.0241 (4)

	U11	U22	U33	U12	U13	U23
Sm1	0.01437 (6)	0.01882 (5)	0.01808 (6)	0.00429 (3)	0.00325 (3)	0.00391 (3)
O1	0.0194 (6)	0.0320 (6)	0.0198 (6)	0.0078 (5)	0.0009 (5)	0.0018 (5)
O1W	0.0274 (7)	0.0365 (7)	0.0393 (8)	0.0103 (6)	0.0122 (6)	0.0173 (6)
O2	0.0209 (6)	0.0605 (9)	0.0234 (6)	0.0171 (6)	0.0007 (5)	−0.0023 (6)
O2W	0.0519 (11)	0.0872 (14)	0.0500 (11)	0.0134 (10)	0.0081 (8)	0.0216 (10)
O3	0.0422 (9)	0.0771 (11)	0.0373 (8)	0.0086 (8)	0.0032 (7)	0.0328 (8)
O4	0.0185 (6)	0.0208 (6)	0.0340 (7)	0.0063 (5)	0.0027 (5)	0.0084 (5)
O5	0.0190 (6)	0.0254 (6)	0.0420 (7)	0.0076 (5)	0.0066 (5)	0.0109 (5)
O6	0.0413 (9)	0.0343 (8)	0.0739 (12)	−0.0010 (7)	0.0068 (8)	0.0225 (8)
O7	0.0377 (7)	0.0244 (6)	0.0275 (7)	0.0027 (5)	0.0086 (6)	0.0033 (5)
O8	0.0275 (6)	0.0257 (6)	0.0250 (6)	0.0059 (5)	0.0077 (5)	0.0046 (5)
O9	0.224 (3)	0.0984 (18)	0.0477 (12)	0.057 (2)	0.0579 (17)	0.0054 (12)
C1	0.0355 (11)	0.0413 (11)	0.0270 (10)	0.0019 (8)	0.0010 (8)	0.0113 (8)
C2	0.0549 (14)	0.0517 (13)	0.0255 (10)	0.0117 (10)	0.0127 (10)	0.0080 (9)
C3	0.0507 (14)	0.0636 (15)	0.0366 (12)	0.0248 (11)	0.0167 (10)	0.0062 (10)
C4	0.0420 (12)	0.0539 (12)	0.0298 (10)	0.0225 (10)	0.0066 (9)	0.0067 (9)
C5	0.0336 (10)	0.0350 (10)	0.0244 (9)	0.0083 (8)	0.0038 (8)	0.0033 (7)
C6	0.0297 (10)	0.0445 (11)	0.0302 (10)	0.0073 (8)	0.0038 (8)	0.0095 (8)
C7	0.0271 (9)	0.0444 (11)	0.0255 (9)	0.0113 (8)	0.0050 (8)	0.0039 (8)
C8	0.0260 (9)	0.0455 (11)	0.0231 (9)	0.0159 (8)	0.0047 (8)	0.0022 (8)
C9	0.0225 (9)	0.0256 (8)	0.0217 (9)	0.0056 (7)	0.0024 (7)	0.0017 (7)
C10	0.0425 (12)	0.0257 (9)	0.0333 (10)	0.0021 (8)	0.0039 (9)	0.0059 (8)
C11	0.0544 (13)	0.0226 (9)	0.0425 (12)	0.0029 (9)	0.0067 (10)	0.0115 (8)
C12	0.0588 (15)	0.0289 (10)	0.0549 (14)	0.0175 (10)	0.0061 (11)	0.0179 (10)
C13	0.0418 (12)	0.0326 (10)	0.0466 (12)	0.0125 (9)	0.0050 (10)	0.0121 (9)
C14	0.0398 (11)	0.0236 (9)	0.0287 (9)	0.0075 (8)	0.0070 (8)	0.0061 (7)
C15	0.0391 (11)	0.0235 (9)	0.0373 (10)	0.0069 (8)	0.0053 (9)	0.0116 (8)
C16	0.0304 (10)	0.0258 (9)	0.0370 (10)	0.0069 (7)	0.0072 (8)	0.0089 (8)
C17	0.0239 (9)	0.0256 (9)	0.0389 (10)	0.0052 (7)	0.0087 (8)	0.0086 (8)
C18	0.0215 (9)	0.0216 (8)	0.0222 (8)	0.0068 (6)	0.0047 (7)	0.0036 (6)
C19	0.096 (2)	0.0696 (18)	0.0382 (14)	0.0266 (16)	0.0186 (14)	−0.0042 (12)
C20	0.095 (2)	0.0618 (18)	0.0569 (18)	0.0250 (16)	0.0176 (16)	−0.0221 (14)
C21	0.116 (3)	0.0413 (14)	0.074 (2)	0.0186 (15)	0.0223 (19)	−0.0111 (14)
C22	0.091 (2)	0.0405 (13)	0.0580 (16)	0.0123 (13)	0.0192 (15)	−0.0024 (12)
C23	0.0502 (13)	0.0402 (12)	0.0371 (12)	0.0117 (10)	0.0068 (10)	−0.0057 (9)
C24	0.086 (2)	0.0462 (13)	0.0402 (13)	0.0215 (13)	0.0153 (13)	−0.0018 (10)
C25	0.0472 (12)	0.0391 (11)	0.0306 (10)	0.0121 (9)	0.0084 (9)	0.0021 (8)
C26	0.0350 (10)	0.0364 (10)	0.0251 (9)	0.0112 (8)	0.0072 (8)	0.0019 (8)
C27	0.0175 (8)	0.0307 (9)	0.0240 (9)	0.0070 (7)	0.0024 (7)	0.0030 (7)

Sm1—O1i	2.3695 (11)	C5—C6	1.392 (3)
Sm1—O4ii	2.3973 (11)	C5—C7	1.464 (3)
Sm1—O1W	2.4517 (13)	C6—H6A	0.9300
Sm1—O2	2.4524 (12)	C7—C8	1.313 (3)
Sm1—O8	2.4598 (12)	C7—H7A	0.9300
Sm1—O7	2.4905 (12)	C8—C9	1.470 (2)
Sm1—O5	2.4919 (12)	C8—H8A	0.9300
Sm1—O4	2.5176 (11)	C10—C11	1.382 (3)
Sm1—O1	2.5861 (11)	C10—C15	1.387 (3)
Sm1—C27	2.8616 (17)	C11—C12	1.375 (3)
Sm1—C9	2.8959 (17)	C11—H11A	0.9300
Sm1—C18	2.8991 (16)	C12—C13	1.390 (3)
O1—C9	1.283 (2)	C12—H12A	0.9300
O1—Sm1i	2.3695 (11)	C13—C14	1.391 (3)
O1W—H1WA	0.824 (15)	C13—H13A	0.9300
O1W—H1WB	0.834 (16)	C14—C15	1.397 (3)
O2—C9	1.249 (2)	C14—C16	1.465 (2)
O2W—H2WA	0.844 (17)	C15—H15A	0.9300
O2W—H2WB	0.814 (17)	C16—C17	1.322 (3)
O3—C1	1.374 (3)	C16—H16A	0.9300
O3—H3	0.906 (17)	C17—C18	1.463 (2)
O4—C18	1.278 (2)	C17—H17A	0.9300
O4—Sm1ii	2.3973 (11)	C19—C20	1.369 (4)
O5—C18	1.256 (2)	C19—C24	1.379 (3)
O6—C10	1.360 (3)	C20—C21	1.365 (5)
O6—H6	0.923 (17)	C20—H20A	0.9300
O7—C27	1.264 (2)	C21—C22	1.384 (4)
O8—C27	1.267 (2)	C21—H21A	0.9300
O9—C19	1.374 (4)	C22—C23	1.384 (3)
O9—H9	0.944 (19)	C22—H22A	0.9300
C1—C2	1.375 (3)	C23—C24	1.384 (4)
C1—C6	1.385 (3)	C23—C25	1.468 (3)
C2—C3	1.385 (3)	C24—H24A	0.9300
C2—H2A	0.9300	C25—C26	1.321 (3)
C3—C4	1.381 (3)	C25—H25A	0.9300
C3—H3A	0.9300	C26—C27	1.473 (2)
C4—C5	1.387 (3)	C26—H26A	0.9300
C4—H4A	0.9300
O1i—Sm1—O4ii	155.55 (4)	C1—C2—H2A	120.2
O1i—Sm1—O1W	79.70 (5)	C3—C2—H2A	120.2
O4ii—Sm1—O1W	87.34 (4)	C4—C3—C2	120.7 (2)
O1i—Sm1—O2	119.15 (4)	C4—C3—H3A	119.7
O4ii—Sm1—O2	78.18 (4)	C2—C3—H3A	119.7
O1W—Sm1—O2	79.90 (5)	C3—C4—C5	120.3 (2)
O1i—Sm1—O8	82.67 (4)	C3—C4—H4A	119.9
O4ii—Sm1—O8	88.82 (4)	C5—C4—H4A	119.9
O1W—Sm1—O8	126.86 (4)	C4—C5—C6	118.54 (18)
O2—Sm1—O8	150.00 (4)	C4—C5—C7	123.46 (18)
O1i—Sm1—O7	81.62 (4)	C6—C5—C7	117.80 (17)
O4ii—Sm1—O7	75.09 (4)	C1—C6—C5	120.92 (19)
O1W—Sm1—O7	75.65 (4)	C1—C6—H6A	119.5
O2—Sm1—O7	144.28 (5)	C5—C6—H6A	119.5
O8—Sm1—O7	52.30 (4)	C8—C7—C5	127.42 (18)
O1i—Sm1—O5	81.25 (4)	C8—C7—H7A	116.3
O4ii—Sm1—O5	119.02 (4)	C5—C7—H7A	116.3
O1W—Sm1—O5	147.03 (4)	C7—C8—C9	122.50 (17)
O2—Sm1—O5	86.30 (5)	C7—C8—H8A	118.8
O8—Sm1—O5	76.50 (4)	C9—C8—H8A	118.8
O7—Sm1—O5	127.52 (4)	O2—C9—O1	119.34 (15)
O1i—Sm1—O4	130.35 (4)	O2—C9—C8	121.45 (16)
O4ii—Sm1—O4	67.43 (4)	O1—C9—C8	119.16 (15)
O1W—Sm1—O4	148.72 (4)	O2—C9—Sm1	57.08 (9)
O2—Sm1—O4	77.13 (4)	O1—C9—Sm1	63.25 (8)
O8—Sm1—O4	72.92 (4)	C8—C9—Sm1	167.72 (13)
O7—Sm1—O4	112.86 (4)	O6—C10—C11	122.73 (17)
O5—Sm1—O4	51.62 (4)	O6—C10—C15	117.38 (19)
O1i—Sm1—O1	67.98 (4)	C11—C10—C15	119.9 (2)
O4ii—Sm1—O1	128.01 (4)	C12—C11—C10	119.62 (18)
O1W—Sm1—O1	73.82 (4)	C12—C11—H11A	120.2
O2—Sm1—O1	51.34 (4)	C10—C11—H11A	120.2
O8—Sm1—O1	140.98 (4)	C11—C12—C13	121.2 (2)
O7—Sm1—O1	139.96 (4)	C11—C12—H12A	119.4
O5—Sm1—O1	74.17 (4)	C13—C12—H12A	119.4
O4—Sm1—O1	106.71 (4)	C12—C13—C14	119.5 (2)
O1i—Sm1—C27	82.20 (4)	C12—C13—H13A	120.2
O4ii—Sm1—C27	80.18 (5)	C14—C13—H13A	120.2
O1W—Sm1—C27	101.49 (5)	C13—C14—C15	118.97 (18)
O2—Sm1—C27	158.23 (5)	C13—C14—C16	119.57 (18)
O8—Sm1—C27	26.17 (5)	C15—C14—C16	121.46 (17)
O7—Sm1—C27	26.16 (5)	C10—C15—C14	120.72 (19)
O5—Sm1—C27	102.28 (5)	C10—C15—H15A	119.6
O4—Sm1—C27	92.42 (4)	C14—C15—H15A	119.6
O1—Sm1—C27	150.18 (4)	C17—C16—C14	125.68 (18)
O1i—Sm1—C9	93.84 (4)	C17—C16—H16A	117.2
O4ii—Sm1—C9	102.04 (5)	C14—C16—H16A	117.2
O1W—Sm1—C9	72.73 (5)	C16—C17—C18	124.04 (17)
O2—Sm1—C9	25.32 (5)	C16—C17—H17A	118.0
O8—Sm1—C9	158.51 (5)	C18—C17—H17A	118.0
O7—Sm1—C9	148.35 (4)	O5—C18—O4	118.84 (15)
O5—Sm1—C9	82.02 (5)	O5—C18—C17	123.16 (16)
O4—Sm1—C9	94.00 (4)	O4—C18—C17	118.00 (15)
O1—Sm1—C9	26.30 (4)	O5—C18—Sm1	58.79 (8)
C27—Sm1—C9	173.57 (5)	O4—C18—Sm1	60.05 (8)
O1i—Sm1—C18	105.70 (4)	C17—C18—Sm1	178.01 (12)
O4ii—Sm1—C18	93.51 (4)	C20—C19—O9	121.7 (2)
O1W—Sm1—C18	160.17 (5)	C20—C19—C24	121.1 (3)
O2—Sm1—C18	80.89 (5)	O9—C19—C24	117.2 (3)
O8—Sm1—C18	72.97 (4)	C21—C20—C19	119.3 (2)
O7—Sm1—C18	123.71 (4)	C21—C20—H20A	120.3
O5—Sm1—C18	25.53 (4)	C19—C20—H20A	120.3
O4—Sm1—C18	26.09 (4)	C20—C21—C22	120.5 (3)
O1—Sm1—C18	90.30 (4)	C20—C21—H21A	119.7
C27—Sm1—C18	98.18 (5)	C22—C21—H21A	119.7
C9—Sm1—C18	87.75 (5)	C23—C22—C21	120.3 (3)
C9—O1—Sm1i	155.04 (11)	C23—C22—H22A	119.9
C9—O1—Sm1	90.44 (9)	C21—C22—H22A	119.9
Sm1i—O1—Sm1	112.02 (4)	C22—C23—C24	118.8 (2)
Sm1—O1W—H1WA	117.4 (17)	C22—C23—C25	118.7 (2)
Sm1—O1W—H1WB	123.4 (17)	C24—C23—C25	122.5 (2)
H1WA—O1W—H1WB	104.8 (19)	C19—C24—C23	119.9 (3)
C9—O2—Sm1	97.61 (10)	C19—C24—H24A	120.0
H2WA—O2W—H2WB	105 (2)	C23—C24—H24A	120.0
C1—O3—H3	109.8 (18)	C26—C25—C23	127.6 (2)
C18—O4—Sm1ii	153.49 (10)	C26—C25—H25A	116.2
C18—O4—Sm1	93.86 (9)	C23—C25—H25A	116.2
Sm1ii—O4—Sm1	112.57 (4)	C25—C26—C27	123.00 (19)
C18—O5—Sm1	95.67 (10)	C25—C26—H26A	118.5
C10—O6—H6	108.7 (17)	C27—C26—H26A	118.5
C27—O7—Sm1	93.54 (10)	O7—C27—O8	119.10 (15)
C27—O8—Sm1	94.92 (10)	O7—C27—C26	121.68 (16)
C19—O9—H9	109 (3)	O8—C27—C26	119.22 (16)
O3—C1—C2	122.80 (18)	O7—C27—Sm1	60.30 (9)
O3—C1—C6	117.30 (19)	O8—C27—Sm1	58.92 (8)
C2—C1—C6	119.90 (19)	C26—C27—Sm1	176.60 (13)
C1—C2—C3	119.56 (19)
O1i—Sm1—O1—C9	168.85 (12)	O1i—Sm1—C9—O2	−178.87 (11)
O4ii—Sm1—O1—C9	10.38 (11)	O4ii—Sm1—C9—O2	19.83 (12)
O1W—Sm1—O1—C9	83.64 (10)	O1W—Sm1—C9—O2	103.17 (12)
O2—Sm1—O1—C9	−6.26 (10)	O8—Sm1—C9—O2	−99.16 (16)
O8—Sm1—O1—C9	−147.01 (10)	O7—Sm1—C9—O2	100.89 (13)
O7—Sm1—O1—C9	125.36 (10)	O5—Sm1—C9—O2	−98.27 (11)
O5—Sm1—O1—C9	−104.36 (10)	O4—Sm1—C9—O2	−47.93 (12)
O4—Sm1—O1—C9	−63.72 (10)	O1—Sm1—C9—O2	−168.52 (18)
C27—Sm1—O1—C9	168.52 (10)	C18—Sm1—C9—O2	−73.28 (12)
C18—Sm1—O1—C9	−84.31 (10)	O1i—Sm1—C9—O1	−10.35 (11)
O1i—Sm1—O1—Sm1i	0.0	O4ii—Sm1—C9—O1	−171.66 (9)
O4ii—Sm1—O1—Sm1i	−158.47 (4)	O1W—Sm1—C9—O1	−88.32 (10)
O1W—Sm1—O1—Sm1i	−85.21 (6)	O2—Sm1—C9—O1	168.52 (17)
O2—Sm1—O1—Sm1i	−175.11 (8)	O8—Sm1—C9—O1	69.36 (16)
O8—Sm1—O1—Sm1i	44.14 (8)	O7—Sm1—C9—O1	−90.60 (13)
O7—Sm1—O1—Sm1i	−43.49 (8)	O5—Sm1—C9—O1	70.24 (9)
O5—Sm1—O1—Sm1i	86.80 (5)	O4—Sm1—C9—O1	120.58 (9)
O4—Sm1—O1—Sm1i	127.43 (5)	C18—Sm1—C9—O1	95.23 (10)
C27—Sm1—O1—Sm1i	−0.32 (11)	O1i—Sm1—C9—C8	94.1 (6)
C9—Sm1—O1—Sm1i	−168.85 (12)	O4ii—Sm1—C9—C8	−67.2 (6)
C18—Sm1—O1—Sm1i	106.84 (5)	O1W—Sm1—C9—C8	16.2 (6)
O1i—Sm1—O2—C9	1.29 (13)	O2—Sm1—C9—C8	−87.0 (6)
O4ii—Sm1—O2—C9	−160.19 (12)	O8—Sm1—C9—C8	173.9 (5)
O1W—Sm1—O2—C9	−70.81 (11)	O7—Sm1—C9—C8	13.9 (6)
O8—Sm1—O2—C9	133.68 (11)	O5—Sm1—C9—C8	174.7 (6)
O7—Sm1—O2—C9	−118.04 (12)	O4—Sm1—C9—C8	−134.9 (6)
O5—Sm1—O2—C9	79.13 (11)	O1—Sm1—C9—C8	104.5 (6)
O4—Sm1—O2—C9	130.57 (12)	C18—Sm1—C9—C8	−160.3 (6)
O1—Sm1—O2—C9	6.49 (10)	O6—C10—C11—C12	178.7 (2)
C27—Sm1—O2—C9	−166.51 (12)	C15—C10—C11—C12	−0.5 (3)
C18—Sm1—O2—C9	104.25 (12)	C10—C11—C12—C13	−0.5 (3)
O1i—Sm1—O4—C18	21.91 (11)	C11—C12—C13—C14	0.8 (3)
O4ii—Sm1—O4—C18	−177.95 (12)	C12—C13—C14—C15	−0.3 (3)
O1W—Sm1—O4—C18	−139.30 (10)	C12—C13—C14—C16	179.75 (19)
O2—Sm1—O4—C18	−95.58 (10)	O6—C10—C15—C14	−178.21 (18)
O8—Sm1—O4—C18	86.05 (10)	C11—C10—C15—C14	1.1 (3)
O7—Sm1—O4—C18	120.58 (9)	C13—C14—C15—C10	−0.7 (3)
O5—Sm1—O4—C18	−0.04 (9)	C16—C14—C15—C10	179.31 (18)
O1—Sm1—O4—C18	−53.10 (10)	C13—C14—C16—C17	−179.3 (2)
C27—Sm1—O4—C18	103.73 (10)	C15—C14—C16—C17	0.7 (3)
C9—Sm1—O4—C18	−76.57 (10)	C14—C16—C17—C18	−179.51 (17)
O1i—Sm1—O4—Sm1ii	−160.13 (4)	Sm1—O5—C18—O4	−0.08 (16)
O4ii—Sm1—O4—Sm1ii	0.0	Sm1—O5—C18—C17	179.55 (15)
O1W—Sm1—O4—Sm1ii	38.66 (10)	Sm1ii—O4—C18—O5	−175.69 (16)
O2—Sm1—O4—Sm1ii	82.38 (5)	Sm1—O4—C18—O5	0.08 (16)
O8—Sm1—O4—Sm1ii	−96.00 (5)	Sm1ii—O4—C18—C17	4.7 (3)
O7—Sm1—O4—Sm1ii	−61.47 (6)	Sm1—O4—C18—C17	−179.57 (13)
O5—Sm1—O4—Sm1ii	177.91 (7)	Sm1ii—O4—C18—Sm1	−175.8 (3)
O1—Sm1—O4—Sm1ii	124.86 (5)	C16—C17—C18—O5	−3.0 (3)
C27—Sm1—O4—Sm1ii	−78.32 (6)	C16—C17—C18—O4	176.63 (17)
C9—Sm1—O4—Sm1ii	101.38 (6)	O1i—Sm1—C18—O5	17.26 (11)
C18—Sm1—O4—Sm1ii	177.95 (12)	O4ii—Sm1—C18—O5	−178.03 (10)
O1i—Sm1—O5—C18	−163.20 (10)	O1W—Sm1—C18—O5	−86.14 (17)
O4ii—Sm1—O5—C18	2.25 (11)	O2—Sm1—C18—O5	−100.60 (10)
O1W—Sm1—O5—C18	141.53 (11)	O8—Sm1—C18—O5	94.28 (10)
O2—Sm1—O5—C18	76.54 (10)	O7—Sm1—C18—O5	107.58 (10)
O8—Sm1—O5—C18	−78.70 (10)	O4—Sm1—C18—O5	−179.92 (16)
O7—Sm1—O5—C18	−90.91 (11)	O1—Sm1—C18—O5	−49.91 (10)
O4—Sm1—O5—C18	0.04 (9)	C27—Sm1—C18—O5	101.40 (10)
O1—Sm1—O5—C18	127.32 (10)	C9—Sm1—C18—O5	−76.10 (10)
C27—Sm1—O5—C18	−83.23 (10)	O1i—Sm1—C18—O4	−162.82 (9)
C9—Sm1—O5—C18	101.64 (10)	O4ii—Sm1—C18—O4	1.89 (11)
O1i—Sm1—O7—C27	89.35 (11)	O1W—Sm1—C18—O4	93.79 (16)
O4ii—Sm1—O7—C27	−98.15 (11)	O2—Sm1—C18—O4	79.32 (9)
O1W—Sm1—O7—C27	170.79 (11)	O8—Sm1—C18—O4	−85.80 (9)
O2—Sm1—O7—C27	−140.97 (10)	O7—Sm1—C18—O4	−72.50 (10)
O8—Sm1—O7—C27	2.16 (9)	O5—Sm1—C18—O4	179.92 (16)
O5—Sm1—O7—C27	17.23 (12)	O1—Sm1—C18—O4	130.01 (9)
O4—Sm1—O7—C27	−41.05 (11)	C27—Sm1—C18—O4	−78.68 (10)
O1—Sm1—O7—C27	129.50 (10)	C9—Sm1—C18—O4	103.82 (10)
C9—Sm1—O7—C27	173.03 (10)	C24—C19—C20—C21	0.0 (6)
C18—Sm1—O7—C27	−13.98 (12)	C19—C20—C21—C22	0.9 (6)
O1i—Sm1—O8—C27	−87.21 (10)	C20—C21—C22—C23	−1.5 (6)
O4ii—Sm1—O8—C27	69.81 (10)	C21—C22—C23—C24	1.1 (5)
O1W—Sm1—O8—C27	−15.98 (12)	C21—C22—C23—C25	−177.8 (3)
O2—Sm1—O8—C27	133.36 (11)	C20—C19—C24—C23	−0.4 (5)
O7—Sm1—O8—C27	−2.16 (9)	O9—C19—C24—C23	179.8 (3)
O5—Sm1—O8—C27	−169.92 (10)	C22—C23—C24—C19	−0.2 (5)
O4—Sm1—O8—C27	136.53 (10)	C25—C23—C24—C19	178.7 (3)
O1—Sm1—O8—C27	−127.82 (10)	C22—C23—C25—C26	168.4 (3)
C9—Sm1—O8—C27	−169.02 (11)	C24—C23—C25—C26	−10.5 (4)
C18—Sm1—O8—C27	163.84 (11)	C23—C25—C26—C27	−178.1 (2)
O3—C1—C2—C3	−178.3 (2)	Sm1—O7—C27—O8	−3.80 (17)
C6—C1—C2—C3	1.5 (3)	Sm1—O7—C27—C26	176.78 (15)
C1—C2—C3—C4	0.9 (4)	Sm1—O8—C27—O7	3.86 (17)
C2—C3—C4—C5	−1.5 (4)	Sm1—O8—C27—C26	−176.71 (14)
C3—C4—C5—C6	−0.4 (3)	C25—C26—C27—O7	0.8 (3)
C3—C4—C5—C7	174.3 (2)	C25—C26—C27—O8	−178.66 (19)
O3—C1—C6—C5	176.38 (18)	O1i—Sm1—C27—O7	−86.87 (10)
C2—C1—C6—C5	−3.5 (3)	O4ii—Sm1—C27—O7	76.12 (10)
C4—C5—C6—C1	2.9 (3)	O1W—Sm1—C27—O7	−9.11 (11)
C7—C5—C6—C1	−172.11 (18)	O2—Sm1—C27—O7	82.40 (16)
C4—C5—C7—C8	−7.3 (3)	O8—Sm1—C27—O7	−176.12 (17)
C6—C5—C7—C8	167.4 (2)	O5—Sm1—C27—O7	−166.09 (10)
C5—C7—C8—C9	−171.47 (18)	O4—Sm1—C27—O7	142.72 (10)
Sm1—O2—C9—O1	−11.77 (18)	O1—Sm1—C27—O7	−86.56 (14)
Sm1—O2—C9—C8	165.59 (15)	C18—Sm1—C27—O7	168.29 (10)
Sm1i—O1—C9—O2	165.90 (18)	O1i—Sm1—C27—O8	89.25 (10)
Sm1—O1—C9—O2	11.05 (17)	O4ii—Sm1—C27—O8	−107.76 (10)
Sm1i—O1—C9—C8	−11.5 (4)	O1W—Sm1—C27—O8	167.01 (10)
Sm1—O1—C9—C8	−166.37 (15)	O2—Sm1—C27—O8	−101.48 (16)
Sm1i—O1—C9—Sm1	154.8 (3)	O7—Sm1—C27—O8	176.12 (17)
C7—C8—C9—O2	−4.1 (3)	O5—Sm1—C27—O8	10.03 (10)
C7—C8—C9—O1	173.30 (18)	O4—Sm1—C27—O8	−41.16 (10)
C7—C8—C9—Sm1	75.2 (6)	O1—Sm1—C27—O8	89.55 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O5i	0.82 (2)	2.02 (2)	2.8183 (18)	163 (2)
O3—H3···O8iii	0.91 (2)	1.76 (2)	2.6692 (19)	176 (3)
O6—H6···O7iv	0.92 (2)	1.78 (2)	2.7005 (19)	174 (3)
O2W—H2WA···O9v	0.84 (2)	2.15 (2)	2.947 (4)	158 (3)
O1W—H1WB···O2Wii	0.83 (2)	1.86 (2)	2.688 (2)	175 (2)
O2W—H2WB···O3vi	0.81 (2)	1.98 (2)	2.790 (3)	173 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O5i	0.82 (2)	2.02 (2)	2.8183 (18)	163 (2)
O3—H3⋯O8ii	0.91 (2)	1.76 (2)	2.6692 (19)	176 (3)
O6—H6⋯O7iii	0.92 (2)	1.78 (2)	2.7005 (19)	174 (3)
O2W—H2WA⋯O9iv	0.84 (2)	2.15 (2)	2.947 (4)	158 (3)
O1W—H1WB⋯O2Wv	0.83 (2)	1.86 (2)	2.688 (2)	175 (2)
O2W—H2WB⋯O3vi	0.81 (2)	1.98 (2)	2.790 (3)	173 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .