Tetra­kis(μ-naphthalene-1-acetato-1:2κ2O:O′)bis­(naphthalene-1-acetato)-1κ2O,O′;2κ2O,O′-bis­(1,10-phenanthroline)-1κ2N,N′;2κ2N,N′-europium(III)samarium(III)

Xia, H.-T.; Liu, Y.-F.; Chen, L.; Wang, D.-Q.

doi:10.1107/S1600536808032960

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1419-m1420

doi:10.1107/S1600536808032960

Open

access

Tetrakis(μ-naphthalene-1-acetato-1:2κ²O:O′)bis(naphthalene-1-acetato)-1κ²O,O′;2κ²O,O′-bis(1,10-phenanthroline)-1κ²N,N′;2κ²N,N′-europium(III)samarium(III)

Hai-Tao Xia,^a ^* Yu-Fen Liu,^a Liang Chen ^a and Da-Qi Wang ^b

^aDepartment of Chemical Engineering, Huaihai Institute of Technology, Lianyungang Jiangsu 222005, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: xht161006@hhit.edu.cn

(Received 2 October 2008; accepted 11 October 2008; online 18 October 2008)

In the title compound, [EuSm(C₁₂H₉O₂)₆(C₁₂H₈N₂)₂], the metal site is statistically occupied (50:50) by Eu and Sm atoms, forming a centrosymmetric complex. The metal site is nine-coordinate, in a distorted monocapped square-antiprismatic coordination geometry. Molecules are linked into three chains by C—H⋯π interactions and C—H⋯O hydrogen bonds. The combination of these chains generates a three-dimensional framework structure. One of the bridging naphthalene-1-acetate ligands was found to be disordered over two sites; the site occupancies for the naphthylmethyl group refined to 0.628 (14) and 0.372 (14).

Related literature

For related structures, see: Liu et al. (2007 ); Xia et al. (2007 ).

Experimental

Crystal data

[EuSm(C₁₂H₉O₂)₆(C₁₂H₈N₂)₂]
M_r = 1773.87
Triclinic, $[P \overline 1]$
a = 11.9803 (18) Å
b = 12.4116 (19) Å
c = 15.041 (3) Å
α = 76.333 (3)°
β = 74.517 (3)°
γ = 66.768 (2)°
V = 1958.8 (5) Å³
Z = 1
Mo Kα radiation
μ = 1.60 mm⁻¹
T = 298 (2) K
0.28 × 0.19 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.662, T_max = 0.795
10253 measured reflections
6796 independent reflections
4983 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.128
S = 1.08
6796 reflections
608 parameters
H-atom parameters constrained
Δρ_max = 1.83 e Å⁻³
Δρ_min = −0.88 e Å⁻³

Table 1
Selected bond lengths (Å)

M denotes Eu or Sm.

M—O3ⁱ	2.362 (4)
M—O1	2.385 (5)
M—O2ⁱ	2.396 (5)
M—O6	2.447 (5)
M—O5	2.479 (6)
M—O4	2.509 (5)
M—O3	2.570 (5)
M—N1	2.612 (6)
M—N2	2.627 (6)
Symmetry code: (i) -x+2, -y+2, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C37—H37⋯O2ⁱ	0.93	2.45	3.097 (9)	127
C46—H46⋯O1	0.93	2.38	3.047 (10)	129
C11—H11⋯O5ⁱⁱ	0.93	2.48	3.38 (2)	163
C47—H47⋯O4ⁱⁱⁱ	0.93	2.50	3.352 (10)	153
C35—H35⋯O6^iv	0.93	2.67	3.327 (12)	128
C16—H16⋯Cg1^v	0.93	2.87	3.66 (3)	144
C39—H39⋯Cg2ⁱⁱⁱ	0.93	2.83	3.673 (18)	151
Symmetry codes: (i) -x+2, -y+2, -z+2; (ii) -x+1, -y+2, -z+2; (iii) -x+3, -y+1, -z+2; (iv) -x+2, -y+1, -z+3; (v) x+1, y, z. Cg1 and Cg2 are the centroids of the C7–C12 and C19–C24 rings, respectively.

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032960/at2644sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808032960/at2644Isup2.hkl

checkCIF report

Comment top

As a part of our investigation of the rare earth complexes with 1-naphthylacetic acid (NAA) and 1,10-phenanthroline (phen), we have recently reported the crystal structures of two complexes [Eu(NAA)₃(phen)]₂.2DMF(II) (Liu et al., 2007 A T2403) and [Pr(NAA)₃(phen)]₂.DMF (Xia et al., 2007 A T2404). We report here the crystal structure of a new rare earth complexes with NAA and phen, (I).

In the title complex, the coordination environment of Sm and Eu atoms and coordination modes of the NNA ligands coordinated to the Sm^III and Eu^III ions are in agreement with the complex(II) (Fig.1). The average bond lengths of between the samarium and europium center and carboxylic oxygen atoms are 2.450 (5) Å, shorter than that (2.4725 (5) Å) of complex (II). The dihedral angles of the least-square-plane Sm₂O₂or Eu₂O₂and naphthyl rings are 31.05 (84)°(C3—C12 ring), 53.76 (33)°(C15—C24 ring) and 7.96 (53)°(C27—C36 ring).

The molecules of (I) are linked into three chains sheets by means of C—H···πand C—H···O hydrogen bond (Fig. 2, Fig. 3, Fig. 4 and Table 2). The action of three chains are to link complex into the three-dimensional framework structure. Cg1 and Cg2 are the centroids of the C7—C12 and C19—C24 ring, respectively.

The naphthalene-1-acetate ligand bridged to Sm and Eu were found to be disordered over two sites, the coordinates of these two sites were refined with the occupancies tied to sum to unity, the site occupancies for C2–C12 with attached H atoms and C2'–C12' with attached H atoms refined to 0.628 (14) and 0.372 (14), respectively.

Related literature top

For related structures, see: Liu et al. (2007); Xia et al. (2007).

Experimental top

To a stirred solution of 1-naphthylacetic acid (0.5586 g, 3 mmol) and 1,10-phenanthroline monohydrate (0.198 g, 1 mmol) in 30 ml methanol, and a solution of Sm(NO₃)₃.6H₂O (0.182 g, 0.5 mmol) and Eu(NO₃)₃.6H₂O (0.223 g, 0.5 mmol)in water (10 ml) was added. The mixed solution was heated to 333 K and stirred for 3 h, and then cooled to room temperature. The precipitate was washed with water and then dissolved in DMF. A colourless crystal suitable for X-ray diffraction was obtained by evaporation of DMF solution.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are at the 30% probability level. Unlabelled atoms bonded to Sm or Eu are related to labelled atoms by (2 - x, 2 - y, 2 - z). For clarity, H atoms have been omitted.
	Fig. 2. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···π and C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds [symmetry codes: (A) 2 - x, 2 - y, 2 - z; (B) 1 - x, 2 - y, 2 - z].
	Fig. 3. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···π and C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds [symmetry codes: (C) 3 - x, 1 - y, 2 - z].
	Fig. 4. A larger portion of the crystal structure of (I), showing the formation of a hydrogen-bonded chain built from C—H···O. For clarity, H atoms not involved in the hydrogen bonding have been omitted. Dashed lines indicate hydrogen bonds [symmetry codes: (D) 2 - x, 1 - y, 3 - z].

Tetrakis(µ-naphthalene-1-acetato-1:2κ²O:O')bis(naphthalene-1-acetato)-1κ²O,O';2κ²O,O'-bis(1,10-phenanthroline)-1κ²N,N';2κ²N,N'-europium(III)samarium(III) top

Crystal data top

[EuSm(C₁₂H₉O₂)₆(C₁₂H₈N₂)₂]	Z = 1
M_r = 1773.87	F(000) = 895
Triclinic, P1	D_x = 1.504 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.9803 (18) Å	Cell parameters from 3440 reflections
b = 12.4116 (19) Å	θ = 2.6–25.1°
c = 15.041 (3) Å	µ = 1.60 mm⁻¹
α = 76.333 (3)°	T = 298 K
β = 74.517 (3)°	Block, colourless
γ = 66.768 (2)°	0.28 × 0.19 × 0.15 mm
V = 1958.8 (5) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6796 independent reflections
Radiation source: fine-focus sealed tube	4983 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.662, T_max = 0.795	k = −14→9
10253 measured reflections	l = −17→16

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0343P)² + 6.8621P] where P = (F_o² + 2F_c²)/3
6796 reflections	(Δ/σ)_max = 0.001
608 parameters	Δρ_max = 1.83 e Å⁻³
0 restraints	Δρ_min = −0.88 e Å⁻³

Crystal data top

[EuSm(C₁₂H₉O₂)₆(C₁₂H₈N₂)₂]	γ = 66.768 (2)°
M_r = 1773.87	V = 1958.8 (5) Å³
Triclinic, P1	Z = 1
a = 11.9803 (18) Å	Mo Kα radiation
b = 12.4116 (19) Å	µ = 1.60 mm⁻¹
c = 15.041 (3) Å	T = 298 K
α = 76.333 (3)°	0.28 × 0.19 × 0.15 mm
β = 74.517 (3)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	6796 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4983 reflections with I > 2σ(I)
T_min = 0.662, T_max = 0.795	R_int = 0.032
10253 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.08	Δρ_max = 1.83 e Å⁻³
6796 reflections	Δρ_min = −0.88 e Å⁻³
608 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sm1	1.07826 (4)	0.83074 (3)	1.04773 (3)	0.04137 (14)	0.50
Eu1	1.07826 (4)	0.83074 (3)	1.04773 (3)	0.04137 (14)	0.50
N1	1.2755 (5)	0.6709 (5)	1.1043 (4)	0.0494 (15)
N2	1.1592 (6)	0.6211 (5)	0.9953 (4)	0.0523 (16)
O1	0.9538 (5)	0.8600 (4)	0.9379 (4)	0.0596 (14)
O2	0.8419 (5)	1.0516 (4)	0.8993 (4)	0.0586 (14)
O3	1.0983 (4)	1.0007 (4)	0.9160 (3)	0.0479 (12)
O4	1.2420 (5)	0.8254 (4)	0.9026 (3)	0.0546 (14)
O5	0.9310 (5)	0.7296 (5)	1.1352 (4)	0.0670 (16)
O6	1.0279 (5)	0.7739 (5)	1.2167 (4)	0.0621 (15)
C1	0.8748 (9)	0.9432 (8)	0.8980 (6)	0.069 (3)
C2	0.843 (2)	0.8996 (15)	0.8199 (15)	0.082 (6)	0.628 (14)
H2A	0.9206	0.8573	0.7816	0.098*	0.628 (14)
H2B	0.8023	0.8432	0.8505	0.098*	0.628 (14)
C3	0.762 (4)	0.995 (3)	0.755 (3)	0.084 (10)	0.628 (14)
C4	0.818 (3)	1.042 (2)	0.6701 (19)	0.098 (7)	0.628 (14)
H4	0.9035	1.0132	0.6515	0.117*	0.628 (14)
C5	0.745 (3)	1.132 (3)	0.613 (3)	0.102 (8)	0.628 (14)
H5	0.7826	1.1638	0.5555	0.122*	0.628 (14)
C6	0.617 (4)	1.175 (4)	0.640 (3)	0.100 (11)	0.628 (14)
H6	0.5688	1.2357	0.6020	0.120*	0.628 (14)
C7	0.562 (7)	1.128 (4)	0.726 (4)	0.093 (14)	0.628 (14)
C8	0.634 (4)	1.038 (3)	0.783 (2)	0.081 (8)	0.628 (14)
C9	0.578 (3)	0.991 (3)	0.869 (2)	0.096 (8)	0.628 (14)
H9	0.6268	0.9302	0.9071	0.115*	0.628 (14)
C10	0.450 (2)	1.0336 (19)	0.8965 (16)	0.112 (7)	0.628 (14)
H10	0.4130	1.0020	0.9536	0.134*	0.628 (14)
C11	0.378 (2)	1.1238 (19)	0.8390 (18)	0.109 (7)	0.628 (14)
H11	0.2921	1.1526	0.8576	0.131*	0.628 (14)
C12	0.433 (3)	1.171 (2)	0.754 (3)	0.102 (9)	0.628 (14)
H12	0.3850	1.2315	0.7152	0.123*	0.628 (14)
C2'	0.766 (3)	0.906 (3)	0.882 (2)	0.081 (9)	0.372 (14)
H2'1	0.8018	0.8301	0.8602	0.097*	0.372 (14)
H2'2	0.7091	0.8990	0.9412	0.097*	0.372 (14)
C3'	0.694 (6)	1.001 (4)	0.810 (4)	0.088 (15)	0.372 (14)
C4'	0.568 (6)	1.060 (4)	0.840 (5)	0.093 (14)	0.372 (14)
H4'	0.5309	1.0457	0.9018	0.112*	0.372 (14)
C5'	0.497 (8)	1.139 (6)	0.776 (6)	0.101 (19)	0.372 (14)
H5'	0.4130	1.1782	0.7956	0.121*	0.372 (14)
C6'	0.553 (12)	1.160 (8)	0.683 (6)	0.10 (3)	0.372 (14)
H6'	0.5057	1.2132	0.6405	0.118*	0.372 (14)
C7'	0.679 (7)	1.102 (5)	0.654 (4)	0.099 (14)	0.372 (14)
C8'	0.750 (7)	1.022 (6)	0.718 (6)	0.102 (8)	0.372 (14)
C9'	0.876 (4)	0.964 (4)	0.688 (3)	0.092 (11)	0.372 (14)
H9'	0.9229	0.9111	0.7308	0.110*	0.372 (14)
C10'	0.931 (3)	0.985 (3)	0.595 (3)	0.104 (11)	0.372 (14)
H10'	1.0154	0.9461	0.5757	0.125*	0.372 (14)
C11'	0.860 (4)	1.064 (3)	0.532 (3)	0.104 (11)	0.372 (14)
H11'	0.8976	1.0785	0.4695	0.125*	0.372 (14)
C12'	0.734 (4)	1.123 (3)	0.561 (3)	0.095 (13)	0.372 (14)
H12'	0.6872	1.1759	0.5183	0.114*	0.372 (14)
C13	1.1879 (7)	0.9282 (7)	0.8676 (5)	0.0476 (18)
C14	1.2204 (8)	0.9723 (7)	0.7647 (6)	0.068 (2)
H14A	1.1490	0.9908	0.7375	0.082*
H14B	1.2340	1.0459	0.7590	0.082*
C15	1.3301 (9)	0.8920 (8)	0.7076 (6)	0.070 (2)
C16	1.4319 (10)	0.9214 (10)	0.6720 (8)	0.094 (3)
H16	1.4323	0.9900	0.6867	0.112*
C17	1.5371 (12)	0.8548 (12)	0.6142 (9)	0.113 (4)
H17	1.6058	0.8777	0.5913	0.136*
C18	1.5348 (12)	0.7552 (12)	0.5927 (8)	0.110 (4)
H18	1.6041	0.7089	0.5551	0.132*
C19	1.4310 (11)	0.7202 (10)	0.6254 (7)	0.083 (3)
C20	1.3258 (9)	0.7906 (9)	0.6834 (6)	0.072 (3)
C21	1.2229 (10)	0.7551 (10)	0.7136 (7)	0.082 (3)
H21	1.1526	0.7992	0.7518	0.099*
C22	1.2249 (12)	0.6548 (11)	0.6874 (8)	0.099 (3)
H22	1.1559	0.6321	0.7072	0.119*
C23	1.3300 (14)	0.5884 (12)	0.6315 (9)	0.108 (4)
H23	1.3308	0.5201	0.6156	0.130*
C24	1.4283 (14)	0.6184 (12)	0.6003 (8)	0.108 (4)
H24	1.4965	0.5728	0.5615	0.129*
C25	0.9553 (8)	0.7250 (7)	1.2119 (6)	0.057 (2)
C26	0.8989 (8)	0.6632 (8)	1.3013 (6)	0.074 (3)
H26A	0.8168	0.6703	1.2969	0.089*
H26B	0.8901	0.7020	1.3529	0.089*
C27	0.9768 (8)	0.5329 (8)	1.3208 (6)	0.065 (2)
C28	1.0766 (9)	0.4782 (8)	1.2587 (7)	0.073 (3)
H28	1.0975	0.5213	1.2014	0.087*
C29	1.1493 (10)	0.3589 (9)	1.2779 (8)	0.087 (3)
H29	1.2186	0.3234	1.2347	0.104*
C30	1.1168 (10)	0.2952 (9)	1.3615 (8)	0.084 (3)
H30	1.1644	0.2154	1.3742	0.101*
C31	1.0161 (10)	0.3454 (9)	1.4274 (7)	0.073 (3)
C32	0.9429 (9)	0.4671 (8)	1.4084 (6)	0.066 (2)
C33	0.8409 (9)	0.5175 (9)	1.4775 (7)	0.078 (3)
H33	0.7922	0.5972	1.4663	0.093*
C34	0.8125 (10)	0.4506 (11)	1.5611 (7)	0.089 (3)
H34	0.7444	0.4846	1.6057	0.107*
C35	0.8843 (12)	0.3342 (11)	1.5785 (8)	0.097 (3)
H35	0.8640	0.2904	1.6356	0.116*
C36	0.9831 (11)	0.2804 (10)	1.5165 (8)	0.093 (3)
H36	1.0302	0.2009	1.5312	0.111*
C37	1.3295 (7)	0.6925 (7)	1.1601 (6)	0.059 (2)
H37	1.2984	0.7680	1.1768	0.071*
C38	1.4318 (8)	0.6071 (8)	1.1957 (6)	0.071 (3)
H38	1.4674	0.6263	1.2348	0.085*
C39	1.4777 (8)	0.4974 (8)	1.1727 (6)	0.074 (3)
H39	1.5464	0.4407	1.1951	0.088*
C40	1.4237 (7)	0.4685 (7)	1.1161 (6)	0.059 (2)
C41	1.3198 (7)	0.5590 (6)	1.0821 (5)	0.052 (2)
C42	1.2593 (7)	0.5333 (6)	1.0247 (5)	0.052 (2)
C43	1.3026 (8)	0.4186 (7)	1.0016 (6)	0.063 (2)
C44	1.2385 (9)	0.3975 (8)	0.9463 (7)	0.079 (3)
H44	1.2648	0.3226	0.9293	0.094*
C45	1.1390 (9)	0.4843 (8)	0.9172 (7)	0.073 (3)
H45	1.0959	0.4704	0.8806	0.087*
C46	1.1024 (8)	0.5956 (7)	0.9435 (6)	0.065 (2)
H46	1.0338	0.6554	0.9233	0.078*
C47	1.4646 (9)	0.3538 (8)	1.0900 (7)	0.075 (3)
H47	1.5320	0.2938	1.1118	0.090*
C48	1.4090 (9)	0.3303 (8)	1.0353 (7)	0.075 (3)
H48	1.4397	0.2549	1.0185	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.0466 (2)	0.0276 (2)	0.0416 (2)	−0.00271 (15)	−0.01227 (16)	−0.00413 (14)
Eu1	0.0466 (2)	0.0276 (2)	0.0416 (2)	−0.00271 (15)	−0.01227 (16)	−0.00413 (14)
N1	0.047 (4)	0.041 (4)	0.049 (4)	−0.003 (3)	−0.013 (3)	−0.004 (3)
N2	0.059 (4)	0.033 (3)	0.059 (4)	−0.010 (3)	−0.007 (3)	−0.012 (3)
O1	0.073 (4)	0.040 (3)	0.067 (4)	−0.007 (3)	−0.036 (3)	−0.006 (3)
O2	0.075 (4)	0.037 (3)	0.077 (4)	−0.016 (3)	−0.043 (3)	−0.005 (3)
O3	0.049 (3)	0.033 (3)	0.048 (3)	0.000 (2)	−0.006 (2)	−0.008 (2)
O4	0.057 (3)	0.033 (3)	0.051 (3)	0.002 (2)	−0.005 (3)	−0.004 (2)
O5	0.081 (4)	0.059 (4)	0.063 (4)	−0.030 (3)	−0.009 (3)	−0.009 (3)
O6	0.062 (4)	0.060 (4)	0.049 (3)	−0.012 (3)	−0.012 (3)	0.002 (3)
C1	0.088 (7)	0.054 (6)	0.083 (7)	−0.024 (5)	−0.049 (6)	−0.008 (5)
C2	0.097 (14)	0.066 (10)	0.099 (15)	−0.019 (10)	−0.054 (12)	−0.019 (10)
C3	0.10 (2)	0.069 (15)	0.10 (3)	−0.028 (17)	−0.06 (2)	−0.017 (17)
C4	0.11 (2)	0.084 (18)	0.11 (2)	−0.025 (17)	−0.047 (18)	−0.013 (15)
C5	0.12 (2)	0.085 (16)	0.11 (2)	−0.028 (17)	−0.047 (19)	−0.008 (15)
C6	0.11 (3)	0.08 (2)	0.11 (3)	−0.02 (2)	−0.06 (2)	−0.007 (19)
C7	0.11 (4)	0.08 (2)	0.11 (5)	−0.03 (3)	−0.06 (3)	−0.01 (3)
C8	0.10 (2)	0.068 (15)	0.10 (2)	−0.025 (14)	−0.06 (2)	−0.019 (15)
C9	0.11 (2)	0.076 (17)	0.11 (2)	−0.019 (16)	−0.046 (16)	−0.017 (14)
C10	0.122 (19)	0.098 (16)	0.117 (17)	−0.025 (15)	−0.040 (15)	−0.026 (13)
C11	0.119 (19)	0.090 (15)	0.12 (2)	−0.017 (13)	−0.045 (16)	−0.035 (14)
C12	0.12 (2)	0.084 (16)	0.11 (2)	−0.018 (16)	−0.06 (2)	−0.020 (14)
C2'	0.10 (2)	0.066 (18)	0.09 (2)	−0.027 (18)	−0.051 (19)	−0.013 (17)
C3'	0.11 (4)	0.07 (2)	0.10 (4)	−0.03 (3)	−0.05 (4)	−0.02 (3)
C4'	0.11 (4)	0.08 (3)	0.11 (4)	−0.02 (3)	−0.05 (3)	−0.01 (3)
C5'	0.11 (6)	0.08 (3)	0.11 (6)	−0.02 (4)	−0.06 (4)	−0.02 (3)
C6'	0.11 (7)	0.08 (5)	0.11 (9)	−0.03 (5)	−0.05 (6)	−0.01 (5)
C7'	0.11 (4)	0.08 (3)	0.11 (4)	−0.02 (3)	−0.05 (4)	−0.01 (3)
C8'	0.12 (2)	0.085 (16)	0.11 (2)	−0.028 (17)	−0.047 (19)	−0.008 (15)
C9'	0.11 (3)	0.07 (3)	0.10 (3)	−0.03 (2)	−0.05 (3)	−0.01 (2)
C10'	0.12 (3)	0.08 (2)	0.11 (3)	−0.03 (2)	−0.05 (2)	−0.02 (2)
C11'	0.12 (3)	0.09 (2)	0.11 (3)	−0.03 (2)	−0.05 (2)	−0.01 (2)
C12'	0.12 (3)	0.08 (2)	0.10 (3)	−0.03 (2)	−0.06 (3)	−0.02 (2)
C13	0.050 (5)	0.038 (4)	0.052 (5)	−0.012 (4)	−0.006 (4)	−0.013 (4)
C14	0.073 (6)	0.051 (5)	0.056 (5)	−0.009 (4)	0.006 (4)	−0.009 (4)
C15	0.072 (6)	0.064 (6)	0.063 (6)	−0.018 (5)	0.001 (5)	−0.014 (5)
C16	0.088 (8)	0.084 (8)	0.096 (8)	−0.029 (7)	0.009 (7)	−0.026 (6)
C17	0.096 (9)	0.111 (10)	0.110 (10)	−0.026 (8)	0.012 (7)	−0.029 (8)
C18	0.093 (9)	0.101 (10)	0.100 (9)	−0.005 (8)	0.006 (7)	−0.028 (8)
C19	0.092 (8)	0.080 (8)	0.072 (7)	−0.017 (6)	−0.015 (6)	−0.026 (6)
C20	0.079 (7)	0.069 (6)	0.063 (6)	−0.015 (5)	−0.015 (5)	−0.016 (5)
C21	0.086 (8)	0.082 (8)	0.075 (7)	−0.022 (6)	−0.017 (6)	−0.017 (6)
C22	0.105 (9)	0.099 (9)	0.096 (9)	−0.032 (8)	−0.024 (7)	−0.021 (7)
C23	0.124 (11)	0.106 (10)	0.095 (10)	−0.024 (9)	−0.030 (9)	−0.032 (8)
C24	0.113 (11)	0.103 (10)	0.081 (8)	−0.006 (8)	−0.015 (8)	−0.028 (7)
C25	0.053 (5)	0.040 (5)	0.059 (6)	−0.009 (4)	−0.001 (4)	0.002 (4)
C26	0.071 (6)	0.063 (6)	0.065 (6)	−0.019 (5)	0.004 (5)	0.003 (5)
C27	0.069 (6)	0.059 (6)	0.064 (6)	−0.028 (5)	−0.009 (5)	−0.001 (4)
C28	0.074 (6)	0.064 (6)	0.068 (6)	−0.024 (5)	0.001 (5)	−0.004 (5)
C29	0.085 (7)	0.070 (7)	0.089 (8)	−0.018 (6)	−0.005 (6)	−0.011 (6)
C30	0.091 (8)	0.070 (7)	0.087 (8)	−0.026 (6)	−0.027 (6)	0.001 (6)
C31	0.087 (7)	0.070 (7)	0.071 (6)	−0.042 (6)	−0.022 (6)	0.007 (5)
C32	0.074 (6)	0.069 (6)	0.064 (6)	−0.039 (5)	−0.015 (5)	−0.001 (5)
C33	0.083 (7)	0.082 (7)	0.068 (6)	−0.037 (6)	−0.013 (5)	0.001 (5)
C34	0.091 (8)	0.098 (9)	0.076 (7)	−0.046 (7)	−0.008 (6)	0.000 (6)
C35	0.112 (10)	0.098 (9)	0.075 (8)	−0.046 (8)	−0.021 (7)	0.015 (7)
C36	0.106 (9)	0.080 (8)	0.088 (8)	−0.039 (7)	−0.024 (7)	0.010 (6)
C37	0.053 (5)	0.054 (5)	0.059 (5)	−0.004 (4)	−0.020 (4)	−0.006 (4)
C38	0.059 (6)	0.072 (7)	0.065 (6)	−0.005 (5)	−0.025 (5)	0.001 (5)
C39	0.056 (6)	0.059 (6)	0.072 (6)	0.002 (5)	−0.014 (5)	0.014 (5)
C40	0.048 (5)	0.040 (5)	0.062 (5)	−0.001 (4)	−0.004 (4)	0.007 (4)
C41	0.047 (5)	0.038 (4)	0.051 (5)	−0.005 (4)	−0.001 (4)	0.004 (3)
C42	0.051 (5)	0.033 (4)	0.056 (5)	−0.008 (4)	0.002 (4)	−0.004 (3)
C43	0.063 (6)	0.037 (5)	0.073 (6)	−0.013 (4)	0.002 (5)	−0.006 (4)
C44	0.083 (7)	0.043 (5)	0.089 (7)	−0.008 (5)	0.005 (6)	−0.019 (5)
C45	0.083 (7)	0.055 (6)	0.085 (7)	−0.026 (5)	−0.010 (5)	−0.025 (5)
C46	0.071 (6)	0.048 (5)	0.076 (6)	−0.018 (4)	−0.014 (5)	−0.017 (4)
C47	0.064 (6)	0.045 (6)	0.081 (7)	−0.001 (5)	0.000 (5)	0.007 (5)
C48	0.072 (6)	0.038 (5)	0.083 (7)	−0.003 (5)	0.009 (5)	−0.009 (5)

Geometric parameters (Å, º) top

Sm1—O3ⁱ	2.362 (4)	C11'—H11'	0.9300
Sm1—O1	2.385 (5)	C12'—H12'	0.9300
Sm1—O2ⁱ	2.396 (5)	C13—C14	1.514 (10)
Sm1—O6	2.447 (5)	C14—C15	1.492 (11)
Sm1—O5	2.479 (6)	C14—H14A	0.9700
Sm1—O4	2.509 (5)	C14—H14B	0.9700
Sm1—O3	2.570 (5)	C15—C16	1.348 (13)
Sm1—N1	2.612 (6)	C15—C20	1.414 (13)
Sm1—N2	2.627 (6)	C16—C17	1.400 (14)
Sm1—Eu1ⁱ	3.9500 (9)	C16—H16	0.9300
Sm1—Sm1ⁱ	3.9500 (9)	C17—C18	1.361 (16)
N1—C37	1.314 (9)	C17—H17	0.9300
N1—C41	1.366 (9)	C18—C19	1.406 (15)
N2—C46	1.320 (10)	C18—H18	0.9300
N2—C42	1.358 (9)	C19—C24	1.417 (16)
O1—C1	1.250 (9)	C19—C20	1.419 (13)
O2—C1	1.247 (9)	C20—C21	1.399 (13)
O2—Sm1ⁱ	2.396 (5)	C21—C22	1.381 (14)
O2—Eu1ⁱ	2.396 (5)	C21—H21	0.9300
O3—C13	1.274 (8)	C22—C23	1.384 (16)
O3—Eu1ⁱ	2.362 (4)	C22—H22	0.9300
O3—Sm1ⁱ	2.362 (4)	C23—C24	1.310 (16)
O4—C13	1.240 (8)	C23—H23	0.9300
O5—C25	1.248 (10)	C24—H24	0.9300
O6—C25	1.264 (10)	C25—C26	1.513 (11)
C1—C2	1.586 (17)	C26—C27	1.518 (12)
C1—C2'	1.63 (3)	C26—H26A	0.9700
C2—C3	1.53 (3)	C26—H26B	0.9700
C2—H2A	0.9700	C27—C28	1.351 (12)
C2—H2B	0.9700	C27—C32	1.426 (11)
C3—C4	1.39 (5)	C28—C29	1.396 (12)
C3—C8	1.39 (6)	C28—H28	0.9300
C4—C5	1.39 (4)	C29—C30	1.367 (13)
C4—H4	0.9300	C29—H29	0.9300
C5—C6	1.39 (5)	C30—C31	1.374 (13)
C5—H5	0.9300	C30—H30	0.9300
C6—C7	1.39 (8)	C31—C32	1.421 (13)
C6—H6	0.9300	C31—C36	1.435 (13)
C7—C8	1.39 (6)	C32—C33	1.411 (12)
C7—C12	1.39 (9)	C33—C34	1.374 (12)
C8—C9	1.39 (5)	C33—H33	0.9300
C9—C10	1.39 (4)	C34—C35	1.362 (14)
C9—H9	0.9300	C34—H34	0.9300
C10—C11	1.39 (3)	C35—C36	1.341 (15)
C10—H10	0.9300	C35—H35	0.9300
C11—C12	1.39 (4)	C36—H36	0.9300
C11—H11	0.9300	C37—C38	1.404 (10)
C12—H12	0.9300	C37—H37	0.9300
C2'—C3'	1.55 (6)	C38—C39	1.344 (12)
C2'—H2'1	0.9700	C38—H38	0.9300
C2'—H2'2	0.9700	C39—C40	1.377 (12)
C3'—C4'	1.39 (8)	C39—H39	0.9300
C3'—C8'	1.39 (11)	C40—C47	1.426 (12)
C4'—C5'	1.39 (9)	C40—C41	1.427 (10)
C4'—H4'	0.9300	C41—C42	1.421 (11)
C5'—C6'	1.39 (14)	C42—C43	1.404 (11)
C5'—H5'	0.9300	C43—C44	1.399 (13)
C6'—C7'	1.39 (15)	C43—C48	1.437 (12)
C6'—H6'	0.9300	C44—C45	1.348 (12)
C7'—C12'	1.39 (8)	C44—H44	0.9300
C7'—C8'	1.39 (8)	C45—C46	1.394 (11)
C8'—C9'	1.39 (9)	C45—H45	0.9300
C9'—C10'	1.39 (5)	C46—H46	0.9300
C9'—H9'	0.9300	C47—C48	1.328 (13)
C10'—C11'	1.39 (4)	C47—H47	0.9300
C10'—H10'	0.9300	C48—H48	0.9300
C11'—C12'	1.39 (5)

O3ⁱ—Sm1—O1	75.35 (17)	C6'—C7'—C8'	120 (7)
O3ⁱ—Sm1—O2ⁱ	76.63 (18)	C12'—C7'—C8'	120 (7)
O1—Sm1—O2ⁱ	136.94 (17)	C3'—C8'—C9'	120 (6)
O3ⁱ—Sm1—O6	80.85 (17)	C3'—C8'—C7'	120 (7)
O1—Sm1—O6	126.6 (2)	C9'—C8'—C7'	120 (8)
O2ⁱ—Sm1—O6	79.5 (2)	C10'—C9'—C8'	120 (5)
O3ⁱ—Sm1—O5	81.14 (18)	C10'—C9'—H9'	120.0
O1—Sm1—O5	76.8 (2)	C8'—C9'—H9'	120.0
O2ⁱ—Sm1—O5	129.6 (2)	C9'—C10'—C11'	120 (4)
O6—Sm1—O5	52.4 (2)	C9'—C10'—H10'	120.0
O3ⁱ—Sm1—O4	124.70 (16)	C11'—C10'—H10'	120.0
O1—Sm1—O4	82.14 (18)	C10'—C11'—C12'	120 (4)
O2ⁱ—Sm1—O4	87.72 (19)	C10'—C11'—H11'	120.0
O6—Sm1—O4	147.99 (18)	C12'—C11'—H11'	120.0
O5—Sm1—O4	140.92 (18)	C7'—C12'—C11'	120 (5)
O3ⁱ—Sm1—O3	73.64 (18)	C7'—C12'—H12'	120.0
O1—Sm1—O3	69.34 (17)	C11'—C12'—H12'	120.0
O2ⁱ—Sm1—O3	71.77 (17)	O4—C13—O3	121.4 (7)
O6—Sm1—O3	145.08 (18)	O4—C13—C14	122.0 (7)
O5—Sm1—O3	141.76 (18)	O3—C13—C14	116.5 (7)
O4—Sm1—O3	51.14 (15)	C15—C14—C13	117.6 (7)
O3ⁱ—Sm1—N1	144.94 (18)	C15—C14—H14A	107.9
O1—Sm1—N1	138.67 (19)	C13—C14—H14A	107.9
O2ⁱ—Sm1—N1	78.07 (19)	C15—C14—H14B	107.9
O6—Sm1—N1	70.97 (18)	C13—C14—H14B	107.9
O5—Sm1—N1	97.0 (2)	H14A—C14—H14B	107.2
O4—Sm1—N1	77.75 (17)	C16—C15—C20	119.0 (9)
O3—Sm1—N1	120.13 (17)	C16—C15—C14	119.6 (9)
O3ⁱ—Sm1—N2	145.13 (19)	C20—C15—C14	121.2 (9)
O1—Sm1—N2	76.94 (19)	C15—C16—C17	123.8 (11)
O2ⁱ—Sm1—N2	138.0 (2)	C15—C16—H16	118.1
O6—Sm1—N2	99.40 (19)	C17—C16—H16	118.1
O5—Sm1—N2	72.25 (19)	C18—C17—C16	117.5 (12)
O4—Sm1—N2	71.10 (18)	C18—C17—H17	121.3
O3—Sm1—N2	115.18 (17)	C16—C17—H17	121.3
N1—Sm1—N2	62.5 (2)	C17—C18—C19	122.0 (12)
O3ⁱ—Sm1—Eu1ⁱ	38.63 (11)	C17—C18—H18	119.0
O1—Sm1—Eu1ⁱ	67.62 (12)	C19—C18—H18	119.0
O2ⁱ—Sm1—Eu1ⁱ	70.01 (12)	C18—C19—C24	121.5 (12)
O6—Sm1—Eu1ⁱ	116.00 (13)	C18—C19—C20	118.8 (11)
O5—Sm1—Eu1ⁱ	114.77 (14)	C24—C19—C20	119.6 (11)
O4—Sm1—Eu1ⁱ	86.11 (11)	C21—C20—C15	123.5 (9)
O3—Sm1—Eu1ⁱ	35.01 (10)	C21—C20—C19	117.7 (10)
N1—Sm1—Eu1ⁱ	144.69 (14)	C15—C20—C19	118.8 (10)
N2—Sm1—Eu1ⁱ	140.12 (14)	C22—C21—C20	120.5 (11)
O3ⁱ—Sm1—Sm1ⁱ	38.63 (11)	C22—C21—H21	119.7
O1—Sm1—Sm1ⁱ	67.62 (12)	C20—C21—H21	119.7
O2ⁱ—Sm1—Sm1ⁱ	70.01 (12)	C21—C22—C23	119.7 (12)
O6—Sm1—Sm1ⁱ	116.00 (13)	C21—C22—H22	120.1
O5—Sm1—Sm1ⁱ	114.77 (14)	C23—C22—H22	120.1
O4—Sm1—Sm1ⁱ	86.11 (11)	C24—C23—C22	122.3 (14)
O3—Sm1—Sm1ⁱ	35.01 (10)	C24—C23—H23	118.9
N1—Sm1—Sm1ⁱ	144.69 (14)	C22—C23—H23	118.9
N2—Sm1—Sm1ⁱ	140.12 (14)	C23—C24—C19	120.1 (13)
Eu1ⁱ—Sm1—Sm1ⁱ	0.000 (14)	C23—C24—H24	119.9
C37—N1—C41	118.0 (7)	C19—C24—H24	119.9
C37—N1—Sm1	121.5 (5)	O5—C25—O6	120.0 (7)
C41—N1—Sm1	120.4 (5)	O5—C25—C26	121.7 (9)
C46—N2—C42	117.8 (7)	O6—C25—C26	118.2 (9)
C46—N2—Sm1	122.0 (5)	C25—C26—C27	112.2 (7)
C42—N2—Sm1	120.2 (5)	C25—C26—H26A	109.2
C1—O1—Sm1	138.5 (5)	C27—C26—H26A	109.2
C1—O2—Sm1ⁱ	133.7 (5)	C25—C26—H26B	109.2
C1—O2—Eu1ⁱ	133.7 (5)	C27—C26—H26B	109.2
C13—O3—Eu1ⁱ	159.7 (5)	H26A—C26—H26B	107.9
C13—O3—Sm1ⁱ	159.7 (5)	C28—C27—C32	119.5 (9)
C13—O3—Sm1	90.9 (4)	C28—C27—C26	122.4 (8)
Eu1ⁱ—O3—Sm1	106.36 (18)	C32—C27—C26	118.2 (8)
Sm1ⁱ—O3—Sm1	106.36 (18)	C27—C28—C29	122.0 (9)
C13—O4—Sm1	94.6 (4)	C27—C28—H28	119.0
C25—O5—Sm1	93.1 (5)	C29—C28—H28	119.0
C25—O6—Sm1	94.2 (5)	C30—C29—C28	118.8 (10)
O2—C1—O1	128.1 (8)	C30—C29—H29	120.6
O2—C1—C2	119.5 (9)	C28—C29—H29	120.6
O1—C1—C2	110.6 (9)	C29—C30—C31	122.0 (10)
O2—C1—C2'	112.8 (13)	C29—C30—H30	119.0
O1—C1—C2'	113.6 (12)	C31—C30—H30	119.0
C3—C2—C1	116.9 (16)	C30—C31—C32	119.2 (9)
C3—C2—H2A	108.1	C30—C31—C36	122.6 (10)
C1—C2—H2A	108.1	C32—C31—C36	118.2 (10)
C3—C2—H2B	108.1	C33—C32—C31	118.4 (9)
C1—C2—H2B	108.1	C33—C32—C27	123.1 (9)
H2A—C2—H2B	107.3	C31—C32—C27	118.5 (9)
C4—C3—C8	120 (3)	C34—C33—C32	120.9 (10)
C4—C3—C2	119 (3)	C34—C33—H33	119.5
C8—C3—C2	121 (4)	C32—C33—H33	119.5
C3—C4—C5	120 (4)	C35—C34—C33	119.9 (11)
C3—C4—H4	120.0	C35—C34—H34	120.1
C5—C4—H4	120.0	C33—C34—H34	120.1
C4—C5—C6	120 (4)	C36—C35—C34	122.6 (11)
C4—C5—H5	120.0	C36—C35—H35	118.7
C6—C5—H5	120.0	C34—C35—H35	118.7
C5—C6—C7	120 (4)	C35—C36—C31	120.0 (11)
C5—C6—H6	120.0	C35—C36—H36	120.0
C7—C6—H6	120.0	C31—C36—H36	120.0
C8—C7—C12	120 (6)	N1—C37—C38	123.1 (8)
C8—C7—C6	120 (6)	N1—C37—H37	118.4
C12—C7—C6	120 (4)	C38—C37—H37	118.4
C3—C8—C7	120 (4)	C39—C38—C37	119.3 (9)
C3—C8—C9	120 (4)	C39—C38—H38	120.3
C7—C8—C9	120 (5)	C37—C38—H38	120.3
C10—C9—C8	120 (3)	C38—C39—C40	120.3 (8)
C10—C9—H9	120.0	C38—C39—H39	119.8
C8—C9—H9	120.0	C40—C39—H39	119.8
C11—C10—C9	120 (2)	C39—C40—C47	124.0 (8)
C11—C10—H10	120.0	C39—C40—C41	117.8 (8)
C9—C10—H10	120.0	C47—C40—C41	118.2 (9)
C10—C11—C12	120 (3)	N1—C41—C42	118.5 (7)
C10—C11—H11	120.0	N1—C41—C40	121.4 (8)
C12—C11—H11	120.0	C42—C41—C40	120.1 (7)
C11—C12—C7	120 (4)	N2—C42—C43	122.1 (8)
C11—C12—H12	120.0	N2—C42—C41	118.3 (7)
C7—C12—H12	120.0	C43—C42—C41	119.5 (8)
C3'—C2'—C1	110 (3)	C44—C43—C42	117.3 (8)
C3'—C2'—H2'1	109.7	C44—C43—C48	123.7 (9)
C1—C2'—H2'1	109.7	C42—C43—C48	119.0 (9)
C3'—C2'—H2'2	109.7	C45—C44—C43	120.7 (9)
C1—C2'—H2'2	109.7	C45—C44—H44	119.6
H2'1—C2'—H2'2	108.2	C43—C44—H44	119.6
C4'—C3'—C8'	120 (7)	C44—C45—C46	118.1 (9)
C4'—C3'—C2'	118 (5)	C44—C45—H45	120.9
C8'—C3'—C2'	122 (6)	C46—C45—H45	120.9
C3'—C4'—C5'	120 (8)	N2—C46—C45	124.0 (9)
C3'—C4'—H4'	120.0	N2—C46—H46	118.0
C5'—C4'—H4'	120.0	C45—C46—H46	118.0
C6'—C5'—C4'	120 (8)	C48—C47—C40	121.7 (9)
C6'—C5'—H5'	120.0	C48—C47—H47	119.1
C4'—C5'—H5'	120.0	C40—C47—H47	119.1
C7'—C6'—C5'	120 (8)	C47—C48—C43	121.5 (9)
C7'—C6'—H6'	120.0	C47—C48—H48	119.3
C5'—C6'—H6'	120.0	C43—C48—H48	119.3
C6'—C7'—C12'	120 (6)

O3ⁱ—Sm1—N1—C37	−26.9 (7)	C12—C7—C8—C9	0 (5)
O1—Sm1—N1—C37	170.6 (5)	C6—C7—C8—C9	180 (3)
O2ⁱ—Sm1—N1—C37	17.6 (6)	C3—C8—C9—C10	180 (2)
O6—Sm1—N1—C37	−65.3 (6)	C7—C8—C9—C10	0 (4)
O5—Sm1—N1—C37	−111.4 (6)	C8—C9—C10—C11	0 (4)
O4—Sm1—N1—C37	107.9 (6)	C9—C10—C11—C12	0 (3)
O3—Sm1—N1—C37	78.1 (6)	C10—C11—C12—C7	0 (4)
N2—Sm1—N1—C37	−177.2 (6)	C8—C7—C12—C11	0 (6)
Eu1ⁱ—Sm1—N1—C37	43.1 (7)	C6—C7—C12—C11	180 (3)
Sm1ⁱ—Sm1—N1—C37	43.1 (7)	O2—C1—C2'—C3'	39 (4)
O3ⁱ—Sm1—N1—C41	148.1 (5)	O1—C1—C2'—C3'	−165 (3)
O1—Sm1—N1—C41	−14.4 (7)	C2—C1—C2'—C3'	−70 (3)
O2ⁱ—Sm1—N1—C41	−167.3 (6)	C1—C2'—C3'—C4'	−120 (4)
O6—Sm1—N1—C41	109.8 (6)	C1—C2'—C3'—C8'	66 (5)
O5—Sm1—N1—C41	63.6 (5)	C8'—C3'—C4'—C5'	0 (8)
O4—Sm1—N1—C41	−77.1 (5)	C2'—C3'—C4'—C5'	−175 (4)
O3—Sm1—N1—C41	−106.8 (5)	C3'—C4'—C5'—C6'	0 (9)
N2—Sm1—N1—C41	−2.2 (5)	C4'—C5'—C6'—C7'	0 (11)
Eu1ⁱ—Sm1—N1—C41	−141.9 (4)	C5'—C6'—C7'—C12'	180 (6)
Sm1ⁱ—Sm1—N1—C41	−141.9 (4)	C5'—C6'—C7'—C8'	0 (10)
O3ⁱ—Sm1—N2—C46	28.9 (8)	C4'—C3'—C8'—C9'	180 (5)
O1—Sm1—N2—C46	−9.2 (6)	C2'—C3'—C8'—C9'	−5 (8)
O2ⁱ—Sm1—N2—C46	−158.9 (6)	C4'—C3'—C8'—C7'	0 (8)
O6—Sm1—N2—C46	116.3 (6)	C2'—C3'—C8'—C7'	175 (4)
O5—Sm1—N2—C46	70.9 (6)	C6'—C7'—C8'—C3'	0 (9)
O4—Sm1—N2—C46	−95.3 (6)	C12'—C7'—C8'—C3'	−180 (5)
O3—Sm1—N2—C46	−68.6 (6)	C6'—C7'—C8'—C9'	−180 (6)
N1—Sm1—N2—C46	179.0 (7)	C12'—C7'—C8'—C9'	0 (8)
Eu1ⁱ—Sm1—N2—C46	−36.7 (7)	C3'—C8'—C9'—C10'	180 (4)
Sm1ⁱ—Sm1—N2—C46	−36.7 (7)	C7'—C8'—C9'—C10'	0 (8)
O3ⁱ—Sm1—N2—C42	−148.3 (5)	C8'—C9'—C10'—C11'	0 (6)
O1—Sm1—N2—C42	173.6 (6)	C9'—C10'—C11'—C12'	0 (5)
O2ⁱ—Sm1—N2—C42	23.9 (7)	C6'—C7'—C12'—C11'	180 (5)
O6—Sm1—N2—C42	−60.8 (6)	C8'—C7'—C12'—C11'	0 (7)
O5—Sm1—N2—C42	−106.2 (6)	C10'—C11'—C12'—C7'	0 (6)
O4—Sm1—N2—C42	87.6 (5)	Sm1—O4—C13—O3	14.5 (8)
O3—Sm1—N2—C42	114.2 (5)	Sm1—O4—C13—C14	−162.5 (7)
N1—Sm1—N2—C42	1.9 (5)	Eu1ⁱ—O3—C13—O4	−162.9 (10)
Eu1ⁱ—Sm1—N2—C42	146.1 (4)	Sm1ⁱ—O3—C13—O4	−162.9 (10)
Sm1ⁱ—Sm1—N2—C42	146.1 (4)	Sm1—O3—C13—O4	−14.1 (7)
O3ⁱ—Sm1—O1—C1	27.9 (9)	Eu1ⁱ—O3—C13—C14	14.2 (18)
O2ⁱ—Sm1—O1—C1	−23.1 (10)	Sm1ⁱ—O3—C13—C14	14.2 (18)
O6—Sm1—O1—C1	94.4 (9)	Sm1—O3—C13—C14	163.0 (6)
O5—Sm1—O1—C1	112.0 (9)	O4—C13—C14—C15	−6.8 (13)
O4—Sm1—O1—C1	−101.2 (9)	O3—C13—C14—C15	176.1 (8)
O3—Sm1—O1—C1	−49.8 (9)	C13—C14—C15—C16	−112.2 (10)
N1—Sm1—O1—C1	−162.4 (8)	C13—C14—C15—C20	73.3 (12)
N2—Sm1—O1—C1	−173.5 (9)	C20—C15—C16—C17	−2.3 (17)
Eu1ⁱ—Sm1—O1—C1	−12.2 (9)	C14—C15—C16—C17	−177.0 (11)
Sm1ⁱ—Sm1—O1—C1	−12.2 (9)	C15—C16—C17—C18	0.5 (19)
O3ⁱ—Sm1—O3—C13	−169.2 (5)	C16—C17—C18—C19	1 (2)
O1—Sm1—O3—C13	−89.1 (4)	C17—C18—C19—C24	178.0 (12)
O2ⁱ—Sm1—O3—C13	109.8 (4)	C17—C18—C19—C20	−0.5 (18)
O6—Sm1—O3—C13	146.0 (4)	C16—C15—C20—C21	−177.5 (10)
O5—Sm1—O3—C13	−118.4 (5)	C14—C15—C20—C21	−2.9 (14)
O4—Sm1—O3—C13	7.6 (4)	C16—C15—C20—C19	2.7 (14)
N1—Sm1—O3—C13	46.1 (5)	C14—C15—C20—C19	177.2 (8)
N2—Sm1—O3—C13	−25.4 (5)	C18—C19—C20—C21	178.9 (10)
Eu1ⁱ—Sm1—O3—C13	−169.2 (5)	C24—C19—C20—C21	0.3 (15)
Sm1ⁱ—Sm1—O3—C13	−169.2 (5)	C18—C19—C20—C15	−1.3 (15)
O3ⁱ—Sm1—O3—Eu1ⁱ	0.0	C24—C19—C20—C15	−179.9 (9)
O1—Sm1—O3—Eu1ⁱ	80.2 (2)	C15—C20—C21—C22	−180.0 (10)
O2ⁱ—Sm1—O3—Eu1ⁱ	−81.0 (2)	C19—C20—C21—C22	−0.1 (14)
O6—Sm1—O3—Eu1ⁱ	−44.7 (4)	C20—C21—C22—C23	0.7 (16)
O5—Sm1—O3—Eu1ⁱ	50.8 (3)	C21—C22—C23—C24	−1.6 (19)
O4—Sm1—O3—Eu1ⁱ	176.8 (3)	C22—C23—C24—C19	2 (2)
N1—Sm1—O3—Eu1ⁱ	−144.7 (2)	C18—C19—C24—C23	−179.6 (12)
N2—Sm1—O3—Eu1ⁱ	143.8 (2)	C20—C19—C24—C23	−1.1 (17)
Sm1ⁱ—Sm1—O3—Eu1ⁱ	0.0	Sm1—O5—C25—O6	4.5 (8)
O3ⁱ—Sm1—O3—Sm1ⁱ	0.0	Sm1—O5—C25—C26	−176.2 (7)
O1—Sm1—O3—Sm1ⁱ	80.2 (2)	Sm1—O6—C25—O5	−4.6 (8)
O2ⁱ—Sm1—O3—Sm1ⁱ	−81.0 (2)	Sm1—O6—C25—C26	176.1 (6)
O6—Sm1—O3—Sm1ⁱ	−44.7 (4)	O5—C25—C26—C27	89.4 (10)
O5—Sm1—O3—Sm1ⁱ	50.8 (3)	O6—C25—C26—C27	−91.3 (10)
O4—Sm1—O3—Sm1ⁱ	176.8 (3)	C25—C26—C27—C28	−7.3 (13)
N1—Sm1—O3—Sm1ⁱ	−144.7 (2)	C25—C26—C27—C32	172.3 (8)
N2—Sm1—O3—Sm1ⁱ	143.8 (2)	C32—C27—C28—C29	−0.9 (15)
Eu1ⁱ—Sm1—O3—Sm1ⁱ	0.0	C26—C27—C28—C29	178.7 (9)
O3ⁱ—Sm1—O4—C13	−4.1 (5)	C27—C28—C29—C30	1.3 (16)
O1—Sm1—O4—C13	61.9 (5)	C28—C29—C30—C31	−1.0 (16)
O2ⁱ—Sm1—O4—C13	−76.1 (5)	C29—C30—C31—C32	0.2 (15)
O6—Sm1—O4—C13	−142.1 (5)	C29—C30—C31—C36	−178.1 (10)
O5—Sm1—O4—C13	119.6 (5)	C30—C31—C32—C33	−179.0 (9)
O3—Sm1—O4—C13	−7.8 (4)	C36—C31—C32—C33	−0.6 (13)
N1—Sm1—O4—C13	−154.4 (5)	C30—C31—C32—C27	0.2 (13)
N2—Sm1—O4—C13	140.8 (5)	C36—C31—C32—C27	178.6 (9)
Eu1ⁱ—Sm1—O4—C13	−6.0 (4)	C28—C27—C32—C33	179.4 (9)
Sm1ⁱ—Sm1—O4—C13	−6.0 (4)	C26—C27—C32—C33	−0.3 (13)
O3ⁱ—Sm1—O5—C25	−87.8 (5)	C28—C27—C32—C31	0.2 (13)
O1—Sm1—O5—C25	−164.7 (5)	C26—C27—C32—C31	−179.4 (8)
O2ⁱ—Sm1—O5—C25	−23.4 (6)	C31—C32—C33—C34	−0.3 (14)
O6—Sm1—O5—C25	−2.6 (4)	C27—C32—C33—C34	−179.5 (9)
O4—Sm1—O5—C25	136.0 (4)	C32—C33—C34—C35	0.9 (16)
O3—Sm1—O5—C25	−136.6 (5)	C33—C34—C35—C36	−0.4 (18)
N1—Sm1—O5—C25	56.9 (5)	C34—C35—C36—C31	−0.6 (18)
N2—Sm1—O5—C25	115.0 (5)	C30—C31—C36—C35	179.4 (10)
Eu1ⁱ—Sm1—O5—C25	−107.3 (5)	C32—C31—C36—C35	1.1 (15)
Sm1ⁱ—Sm1—O5—C25	−107.3 (5)	C41—N1—C37—C38	1.6 (12)
O3ⁱ—Sm1—O6—C25	88.3 (5)	Sm1—N1—C37—C38	176.7 (6)
O1—Sm1—O6—C25	24.3 (5)	N1—C37—C38—C39	−0.3 (13)
O2ⁱ—Sm1—O6—C25	166.3 (5)	C37—C38—C39—C40	−1.1 (14)
O5—Sm1—O6—C25	2.5 (4)	C38—C39—C40—C47	−178.5 (8)
O4—Sm1—O6—C25	−125.6 (5)	C38—C39—C40—C41	1.0 (13)
O3—Sm1—O6—C25	131.5 (5)	C37—N1—C41—C42	177.7 (7)
N1—Sm1—O6—C25	−112.8 (5)	Sm1—N1—C41—C42	2.5 (9)
N2—Sm1—O6—C25	−56.3 (5)	C37—N1—C41—C40	−1.6 (11)
Eu1ⁱ—Sm1—O6—C25	104.8 (4)	Sm1—N1—C41—C40	−176.8 (5)
Sm1ⁱ—Sm1—O6—C25	104.8 (4)	C39—C40—C41—N1	0.4 (11)
Sm1ⁱ—O2—C1—O1	11.3 (16)	C47—C40—C41—N1	179.9 (7)
Eu1ⁱ—O2—C1—O1	11.3 (16)	C39—C40—C41—C42	−178.9 (7)
Sm1ⁱ—O2—C1—C2	−151.7 (11)	C47—C40—C41—C42	0.6 (11)
Eu1ⁱ—O2—C1—C2	−151.7 (11)	C46—N2—C42—C43	0.0 (11)
Sm1ⁱ—O2—C1—C2'	163.1 (15)	Sm1—N2—C42—C43	177.3 (6)
Eu1ⁱ—O2—C1—C2'	163.1 (15)	C46—N2—C42—C41	−178.8 (7)
Sm1—O1—C1—O2	7.5 (17)	Sm1—N2—C42—C41	−1.5 (9)
Sm1—O1—C1—C2	171.7 (10)	N1—C41—C42—N2	−0.6 (10)
Sm1—O1—C1—C2'	−144.1 (16)	C40—C41—C42—N2	178.7 (7)
O2—C1—C2—C3	−6 (3)	N1—C41—C42—C43	−179.5 (7)
O1—C1—C2—C3	−172 (2)	C40—C41—C42—C43	−0.1 (11)
C2'—C1—C2—C3	86 (3)	N2—C42—C43—C44	0.1 (12)
C1—C2—C3—C4	95 (3)	C41—C42—C43—C44	178.9 (7)
C1—C2—C3—C8	−82 (3)	N2—C42—C43—C48	−179.9 (7)
C8—C3—C4—C5	0 (4)	C41—C42—C43—C48	−1.2 (12)
C2—C3—C4—C5	−177 (2)	C42—C43—C44—C45	−0.3 (13)
C3—C4—C5—C6	0 (4)	C48—C43—C44—C45	179.8 (9)
C4—C5—C6—C7	0 (5)	C43—C44—C45—C46	0.3 (14)
C5—C6—C7—C8	0 (6)	C42—N2—C46—C45	−0.1 (12)
C5—C6—C7—C12	180 (3)	Sm1—N2—C46—C45	−177.3 (7)
C4—C3—C8—C7	0 (4)	C44—C45—C46—N2	−0.1 (14)
C2—C3—C8—C7	177 (3)	C39—C40—C47—C48	179.8 (9)
C4—C3—C8—C9	180 (2)	C41—C40—C47—C48	0.3 (13)
C2—C3—C8—C9	−3 (3)	C40—C47—C48—C43	−1.6 (14)
C12—C7—C8—C3	−180 (3)	C44—C43—C48—C47	−178.0 (9)
C6—C7—C8—C3	0 (6)	C42—C43—C48—C47	2.1 (13)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O2ⁱ	0.93	2.45	3.097 (9)	127
C46—H46···O1	0.93	2.38	3.047 (10)	129
C11—H11···O5ⁱⁱ	0.93	2.48	3.38 (2)	163
C47—H47···O4ⁱⁱⁱ	0.93	2.50	3.352 (10)	153
C35—H35···O6^iv	0.93	2.67	3.327 (12)	128
C16—H16···Cg1^v	0.93	2.87	3.66 (3)	144
C39—H39···Cg2ⁱⁱⁱ	0.93	2.83	3.673 (18)	151

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+2; (iii) −x+3, −y+1, −z+2; (iv) −x+2, −y+1, −z+3; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[EuSm(C₁₂H₉O₂)₆(C₁₂H₈N₂)₂]
M_r	1773.87
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	11.9803 (18), 12.4116 (19), 15.041 (3)
α, β, γ (°)	76.333 (3), 74.517 (3), 66.768 (2)
V (Å³)	1958.8 (5)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.28 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.662, 0.795
No. of measured, independent and observed [I > 2σ(I)] reflections	10253, 6796, 4983
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.128, 1.08
No. of reflections	6796
No. of parameters	608
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.83, −0.88

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Sm1—O3ⁱ	2.362 (4)	Sm1—O4	2.509 (5)
Sm1—O1	2.385 (5)	Sm1—O3	2.570 (5)
Sm1—O2ⁱ	2.396 (5)	Sm1—N1	2.612 (6)
Sm1—O6	2.447 (5)	Sm1—N2	2.627 (6)
Sm1—O5	2.479 (6)

Symmetry code: (i) −x+2, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C37—H37···O2ⁱ	0.93	2.45	3.097 (9)	126.9
C46—H46···O1	0.93	2.38	3.047 (10)	128.9
C11—H11···O5ⁱⁱ	0.93	2.48	3.38 (2)	163.2
C47—H47···O4ⁱⁱⁱ	0.93	2.50	3.352 (10)	152.6
C35—H35···O6^iv	0.93	2.67	3.327 (12)	128.1
C16—H16···Cg1^v	0.93	2.87	3.66 (3)	144.3
C39—H39···Cg2ⁱⁱⁱ	0.93	2.83	3.673 (18)	151.4

Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x+1, −y+2, −z+2; (iii) −x+3, −y+1, −z+2; (iv) −x+2, −y+1, −z+3; (v) x+1, y, z.

Acknowledgements

We acknowledge the financial support of the Huaihai Institute of Technology Science Foundation.

References

Liu, Y.-F., Xia, H.-T., Wang, D.-Q. & Yang, S.-P. (2007). Acta Cryst. E63, m2608–m2609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens. (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Xia, H.-T., Liu, Y.-F., Wang, D.-Q. & Chen, L. (2007). Acta Cryst. E63, m2610–m2611. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.