catena-Poly[[bis­(μ-anilinoacetato-κ2O:O′)bis­(μ-anilinoacetato-κ3O,O′:O)bis­[(1,10-phenanthroline-κ2N,N′)samar­ium(III)]-μ-anilinoacetato-κ2O:O′]

Zhong, H.; Yang, X.-M.; Xie, H.-L.; Luo, C.-J.

doi:10.1107/S1600536807043528

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Retracted: catena-Poly[[bis(μ-anilinoacetato-κ²O:O′)bis(μ-anilinoacetato-κ³O,O′:O)bis[(1,10-phenanthroline-κ²N,N′)samarium(III)]-μ-anilinoacetato-κ²O:O′]

H. Zhong, X.-M. Yang, H.-L. Xie and C.-J. Luo

In the crystal structure of the title compound, [Sm₂(C₈H₈NO₂)₆(C₁₂H₈N₂)₂]_n, the Sm^III atoms are bridged by two terdentate, two bidentate and four mondentate carboxylate groups with an inversion centre between the two Sm^III ions. Each Sm atom is nine-coordinated by two N atoms of 1,10-phenanthroline and seven O atoms of four anilinoacetate ligands. In the crystal structure, the chains are linked by hydrogen bonds into a polymeric ribbon structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043528/at2392sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043528/at2392Isup2.hkl Contains datablock I

CCDC reference: 1233743

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.013 Å
R factor = 0.050
wR factor = 0.152
Data-to-parameter ratio = 18.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         N4
PLAT414_ALERT_2_B Short Intra D-H..H-X       H5     ..  H12     ..       1.81 Ang.

Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.98 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C23
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT331_ALERT_2_C Small Average Phenyl C-C Dist.   C15    -C20           1.37 Ang.
PLAT332_ALERT_2_C Large Phenyl C-C Range           C23    -C28           0.18 Ang.
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C6            1.43 Ang.
PLAT335_ALERT_2_C Large Benzene C-C Range .......  C4     -C6            0.16 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         13
PLAT414_ALERT_2_C Short Intra D-H..H-X       H1     ..  H3A     ..       1.93 Ang.
PLAT420_ALERT_2_C D-H Without Acceptor       N4     -   H4     ...          ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      71.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Sm1         (3)       2.73
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  15 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Daiguebonne et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [Sm₂(C₈H₈NO₂)₆(C₁₂H₈N₂)₂]_n, which are the metal organic framework synthesized by the anilinoacetate ligand and the rare earth metal Sm, are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two Sm^III ions. Each Sm atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The Sm—O bond lengths are in the range 2.414 (3) to 2.822 (4) Å. The Sm—N bond lengths are in the range 2.710 (4) to 2.728 (4) Å. In the crystal structure, N—H···O, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure.

Related literature top

For related literature, see: Allen et al. (1987); Daiguebonne et al. (2000); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000).

Experimental top

Crystals of the title compound (I) were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Samarium (III) nitrate hexahydrate (218.5 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetic acid (146.2 mg, 1 mmol), ammonia (0.5 mol/l, 2 ml) and distilled water (6 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 423 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

	Fig. 1. The structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, -y, 2 - z]. All H atoms have been omitted for clarity.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

catena-Poly[[bis(µ-anilinoacetato-κ²O:O')bis(µ-αnilinoacetato-κ³O,O':O)bis[(1,10-phenanthroline-\k²N,N')samarium(III)]- bis-(µ-anilinoacetato-κ²O:O')] top

Crystal data top

[Sm₂(C₈H₈NO₂)₆(C₁₂H₈N₂)₂]	F(000) = 1572
M_r = 1562.04	D_x = 1.536 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8997 reflections
a = 19.998 (3) Å	θ = 2.7–26.7°
b = 8.498 (2) Å	µ = 1.79 mm⁻¹
c = 20.783 (2) Å	T = 273 K
β = 106.998 (5)°	Plane, colourless
V = 3377.7 (10) Å³	0.33 × 0.12 × 0.08 mm
Z = 2

Data collection top

Bruker APEX II area-detector diffractometer	7519 independent reflections
Radiation source: fine-focus sealed tube	4974 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 27.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
T_min = 0.590, T_max = 0.871	k = −10→11
27195 measured reflections	l = −26→26

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) = 0.152	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.1002P)² + 0.285P] where P = (F_o² + 2F_c²)/3
7519 reflections	(Δ/σ)_max = 0.002
403 parameters	Δρ_max = 1.54 e Å⁻³
3 restraints	Δρ_min = −0.81 e Å⁻³

Crystal data top

[Sm₂(C₈H₈NO₂)₆(C₁₂H₈N₂)₂]	V = 3377.7 (10) Å³
M_r = 1562.04	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 19.998 (3) Å	µ = 1.79 mm⁻¹
b = 8.498 (2) Å	T = 273 K
c = 20.783 (2) Å	0.33 × 0.12 × 0.08 mm
β = 106.998 (5)°

Data collection top

Bruker APEX II area-detector diffractometer	7519 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4974 reflections with I > 2σ(I)
T_min = 0.590, T_max = 0.871	R_int = 0.043
27195 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	3 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 0.98	Δρ_max = 1.54 e Å⁻³
7519 reflections	Δρ_min = −0.81 e Å⁻³
403 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
Sm1	0.931196 (13)	0.19068 (3)	0.964300 (12)	0.03994 (12)
O1	0.84626 (17)	−0.0361 (4)	0.91902 (17)	0.0413 (8)
O2	0.94708 (19)	−0.1388 (5)	0.97740 (18)	0.0480 (9)
O3	0.97071 (19)	0.0614 (4)	0.87480 (17)	0.0447 (8)
O4	1.06691 (19)	−0.0829 (4)	0.92152 (17)	0.0473 (9)
O5	0.94009 (19)	0.4211 (4)	1.03423 (17)	0.0447 (8)
O6	1.0073 (2)	0.6128 (5)	1.09082 (17)	0.0531 (10)
N1	0.7968 (2)	0.2338 (6)	0.9669 (2)	0.0444 (10)
N2	0.8342 (3)	0.3067 (5)	0.8547 (2)	0.0451 (11)
N3	1.1177 (2)	−0.0164 (5)	0.8215 (2)	0.0481 (11)
H3A	1.1390	−0.0746	0.8551	0.058*
N4	0.7857 (2)	−0.3269 (5)	0.8983 (2)	0.0447 (11)
H4	0.7628	−0.3419	0.8568	0.054*
N5	0.9861 (2)	0.5266 (5)	1.20625 (19)	0.0436 (11)
H5	1.0160	0.5982	1.2047	0.052*
C1	0.7787 (3)	0.1908 (7)	1.0198 (3)	0.0606 (17)
H1	0.8137	0.1676	1.0592	0.073*
C2	0.7093 (4)	0.1781 (9)	1.0197 (4)	0.080 (2)
H2	0.6981	0.1487	1.0584	0.097*
C3	0.6582 (4)	0.2099 (9)	0.9616 (5)	0.086 (3)
H3	0.6115	0.1989	0.9603	0.103*
C4	0.6742 (4)	0.2571 (10)	0.9056 (4)	0.0717 (19)
C5	0.7467 (3)	0.2673 (7)	0.9095 (3)	0.0508 (14)
C6	0.6212 (5)	0.2936 (13)	0.8394 (6)	0.115 (4)
H6	0.5738	0.2819	0.8348	0.137*
C7	0.6416 (5)	0.3427 (12)	0.7869 (5)	0.098 (3)
H7	0.6080	0.3702	0.7471	0.118*
C8	0.7132 (4)	0.3537 (9)	0.7906 (3)	0.0653 (18)
C9	0.7671 (3)	0.3102 (6)	0.8507 (3)	0.0499 (14)
C10	0.7358 (5)	0.4034 (9)	0.7370 (3)	0.086 (2)
H10	0.7034	0.4381	0.6977	0.103*
C11	0.8045 (5)	0.4019 (9)	0.7413 (3)	0.078 (2)
H11	0.8197	0.4354	0.7054	0.094*
C12	0.8524 (4)	0.3491 (7)	0.8008 (3)	0.0611 (17)
H12	0.8994	0.3434	0.8026	0.073*
C13	1.0287 (3)	0.0024 (6)	0.8770 (2)	0.0408 (12)
C14	1.0520 (3)	0.0521 (7)	0.8172 (3)	0.0525 (14)
H14A	1.0178	0.0188	0.7760	0.063*
H14B	1.0557	0.1658	0.8164	0.063*
C15	1.1463 (3)	0.0134 (8)	0.7697 (3)	0.0604 (16)
C16	1.2074 (4)	−0.0576 (10)	0.7761 (4)	0.074 (2)
H16	1.2277	−0.1203	0.8134	0.089*
C17	1.2401 (4)	−0.0366 (11)	0.7264 (5)	0.090 (2)
H17	1.2833	−0.0832	0.7308	0.108*
C18	1.2091 (6)	0.0522 (10)	0.6712 (5)	0.104 (3)
H18	1.2311	0.0634	0.6376	0.125*
C19	1.1481 (6)	0.1232 (12)	0.6642 (5)	0.106 (3)
H19	1.1275	0.1836	0.6263	0.128*
C20	1.1148 (4)	0.1056 (10)	0.7154 (4)	0.082 (2)
H20	1.0725	0.1555	0.7122	0.098*
C21	0.8834 (3)	−0.1514 (7)	0.9387 (2)	0.0417 (12)
C22	0.8569 (3)	−0.3142 (6)	0.9196 (3)	0.0534 (15)
H22A	0.8754	−0.3514	0.8841	0.064*
H22B	0.8748	−0.3826	0.9582	0.064*
C23	0.7543 (7)	−0.3144 (10)	0.9466 (8)	0.1220 (17)
C24	0.7823 (7)	−0.2775 (10)	1.0106 (7)	0.1220 (17)
H24	0.8300	−0.2575	1.0267	0.146*
C25	0.7405 (6)	−0.2680 (12)	1.0550 (7)	0.1220 (17)
H25	0.7600	−0.2440	1.1003	0.146*
C26	0.6741 (7)	−0.2941 (11)	1.0303 (7)	0.1220 (17)
H26	0.6472	−0.2847	1.0597	0.146*
C27	0.6369 (7)	−0.3372 (11)	0.9601 (7)	0.1220 (17)
H27	0.5893	−0.3591	0.9448	0.146*
C28	0.6792 (6)	−0.3411 (12)	0.9210 (7)	0.1220 (17)
H28	0.6599	−0.3618	0.8754	0.146*
C29	0.9695 (3)	0.4988 (6)	1.0865 (3)	0.0414 (12)
C30	0.9487 (3)	0.4451 (7)	1.1472 (3)	0.0536 (14)
H30A	0.8990	0.4623	1.1392	0.064*
H30B	0.9576	0.3331	1.1537	0.064*
C31	0.9739 (3)	0.4896 (7)	1.2654 (3)	0.0531 (14)
C32	0.9277 (4)	0.3796 (9)	1.2718 (3)	0.0679 (19)
H32	0.9015	0.3244	1.2342	0.081*
C33	0.9192 (6)	0.3492 (13)	1.3339 (5)	0.106 (3)
H33	0.8883	0.2713	1.3385	0.127*
C34	0.9573 (5)	0.4356 (12)	1.3906 (4)	0.099 (3)
H34	0.9497	0.4199	1.4322	0.119*
C35	1.0045 (4)	0.5409 (10)	1.3836 (3)	0.086 (2)
H35	1.0312	0.5954	1.4212	0.103*
C36	1.0143 (4)	0.5699 (9)	1.3219 (3)	0.0692 (18)
H36	1.0477	0.6425	1.3179	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sm1	0.04626 (18)	0.03404 (18)	0.03452 (17)	−0.00154 (11)	0.00400 (11)	0.00062 (11)
O1	0.0414 (18)	0.0306 (19)	0.045 (2)	0.0002 (15)	0.0011 (15)	−0.0031 (15)
O2	0.046 (2)	0.047 (2)	0.043 (2)	−0.0021 (18)	0.0004 (16)	0.0087 (17)
O3	0.054 (2)	0.043 (2)	0.0378 (19)	0.0038 (18)	0.0138 (16)	0.0029 (16)
O4	0.057 (2)	0.046 (2)	0.040 (2)	0.0070 (18)	0.0157 (17)	0.0103 (17)
O5	0.063 (2)	0.0307 (19)	0.0391 (19)	−0.0050 (17)	0.0125 (16)	−0.0051 (15)
O6	0.077 (3)	0.049 (2)	0.0344 (19)	−0.024 (2)	0.0176 (18)	−0.0038 (17)
N1	0.043 (2)	0.038 (2)	0.045 (3)	0.003 (2)	0.002 (2)	−0.008 (2)
N2	0.057 (3)	0.038 (3)	0.032 (2)	0.002 (2)	−0.0015 (19)	0.0013 (18)
N3	0.048 (2)	0.063 (3)	0.039 (2)	0.018 (2)	0.022 (2)	0.023 (2)
N4	0.040 (2)	0.032 (3)	0.051 (3)	−0.0124 (18)	−0.003 (2)	−0.0068 (19)
N5	0.063 (3)	0.041 (3)	0.028 (2)	−0.028 (2)	0.0153 (19)	−0.0057 (17)
C1	0.052 (3)	0.072 (5)	0.056 (4)	0.007 (3)	0.014 (3)	−0.004 (3)
C2	0.057 (4)	0.108 (7)	0.081 (5)	0.001 (4)	0.029 (4)	−0.014 (4)
C3	0.046 (4)	0.090 (7)	0.118 (8)	−0.004 (4)	0.018 (4)	−0.013 (5)
C4	0.052 (4)	0.080 (5)	0.070 (5)	0.005 (4)	−0.002 (3)	−0.017 (4)
C5	0.051 (3)	0.033 (3)	0.059 (4)	0.008 (2)	0.001 (3)	−0.009 (3)
C6	0.052 (5)	0.152 (11)	0.109 (8)	0.019 (5)	−0.024 (5)	−0.037 (7)
C7	0.080 (6)	0.110 (7)	0.073 (6)	0.037 (5)	−0.027 (4)	−0.012 (5)
C8	0.067 (4)	0.063 (4)	0.045 (4)	0.018 (3)	−0.016 (3)	−0.008 (3)
C9	0.057 (3)	0.032 (3)	0.045 (3)	0.005 (2)	−0.009 (3)	−0.004 (2)
C10	0.119 (7)	0.065 (5)	0.046 (4)	0.015 (5)	−0.019 (4)	−0.002 (3)
C11	0.114 (6)	0.075 (5)	0.034 (3)	−0.001 (5)	0.003 (4)	0.011 (3)
C12	0.076 (4)	0.049 (4)	0.048 (4)	−0.003 (3)	0.003 (3)	0.008 (3)
C13	0.050 (3)	0.033 (3)	0.038 (3)	−0.008 (2)	0.010 (2)	−0.002 (2)
C14	0.063 (3)	0.053 (4)	0.043 (3)	0.005 (3)	0.019 (3)	0.010 (3)
C15	0.066 (4)	0.066 (4)	0.055 (4)	−0.009 (3)	0.027 (3)	0.002 (3)
C16	0.075 (5)	0.092 (5)	0.067 (4)	0.005 (4)	0.037 (4)	−0.001 (4)
C17	0.082 (5)	0.094 (7)	0.109 (7)	−0.009 (5)	0.053 (5)	−0.011 (5)
C18	0.138 (8)	0.077 (6)	0.138 (9)	−0.014 (6)	0.104 (7)	−0.002 (6)
C19	0.153 (9)	0.103 (7)	0.089 (6)	0.015 (7)	0.077 (6)	0.031 (5)
C20	0.098 (6)	0.087 (6)	0.077 (5)	0.001 (5)	0.053 (4)	0.020 (4)
C21	0.044 (3)	0.047 (3)	0.029 (2)	−0.006 (2)	0.004 (2)	−0.004 (2)
C22	0.059 (4)	0.045 (4)	0.052 (3)	0.003 (3)	0.010 (3)	−0.007 (3)
C23	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C24	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C25	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C26	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C27	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C28	0.134 (4)	0.086 (3)	0.169 (5)	0.015 (3)	0.079 (4)	0.031 (3)
C29	0.055 (3)	0.030 (3)	0.038 (3)	−0.001 (2)	0.012 (2)	0.003 (2)
C30	0.073 (4)	0.049 (3)	0.040 (3)	−0.021 (3)	0.018 (3)	−0.005 (2)
C31	0.072 (4)	0.052 (4)	0.033 (3)	−0.001 (3)	0.014 (3)	0.003 (2)
C32	0.071 (4)	0.088 (5)	0.046 (3)	−0.034 (4)	0.019 (3)	−0.006 (3)
C33	0.124 (8)	0.134 (8)	0.075 (6)	−0.049 (7)	0.053 (6)	0.002 (5)
C34	0.118 (7)	0.143 (8)	0.044 (4)	−0.029 (6)	0.034 (4)	0.005 (5)
C35	0.112 (6)	0.100 (6)	0.040 (4)	−0.020 (5)	0.013 (4)	−0.008 (4)
C36	0.079 (4)	0.073 (5)	0.052 (4)	−0.018 (4)	0.013 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Sm1—O1	2.559 (3)	C10—H10	0.9300
Sm1—O2	2.822 (4)	C11—C12	1.398 (9)
Sm1—O2ⁱ	2.421 (4)	C11—H11	0.9300
Sm1—O3	2.480 (3)	C12—H12	0.9300
Sm1—O4ⁱ	2.533 (3)	C13—C14	1.509 (7)
Sm1—O5	2.414 (3)	C14—H14A	0.9700
Sm1—O6ⁱⁱ	2.537 (4)	C14—H14B	0.9700
Sm1—N1	2.728 (4)	C15—C16	1.334 (9)
Sm1—N2	2.710 (4)	C15—C20	1.366 (10)
O1—C21	1.225 (6)	C16—C17	1.386 (11)
O2—C21	1.297 (6)	C16—H16	0.9300
O2—Sm1ⁱ	2.421 (4)	C17—C18	1.363 (13)
O3—C13	1.252 (6)	C17—H17	0.9300
O4—C13	1.247 (6)	C18—C19	1.331 (12)
O4—Sm1ⁱ	2.533 (3)	C18—H18	0.9300
O5—C29	1.260 (6)	C19—C20	1.419 (10)
O6—C29	1.215 (6)	C19—H19	0.9300
O6—Sm1ⁱⁱ	2.537 (4)	C20—H20	0.9300
N1—C1	1.307 (8)	C21—C22	1.493 (8)
N1—C5	1.345 (7)	C22—H22A	0.9700
N2—C9	1.321 (8)	C22—H22B	0.9700
N2—C12	1.326 (8)	C23—C24	1.320 (17)
N3—C15	1.383 (7)	C23—C28	1.457 (17)
N3—C14	1.415 (7)	C24—C25	1.418 (14)
N3—H3A	0.8600	C24—H24	0.9300
N4—C23	1.337 (13)	C25—C26	1.293 (16)
N4—C22	1.365 (7)	C25—H25	0.9300
N4—H4	0.8600	C26—C27	1.478 (17)
N5—C31	1.359 (7)	C26—H26	0.9300
N5—C30	1.418 (6)	C27—C28	1.332 (14)
N5—H5	0.8600	C27—H27	0.9300
C1—C2	1.390 (9)	C28—H28	0.9300
C1—H1	0.9300	C29—C30	1.511 (7)
C2—C3	1.363 (12)	C30—H30A	0.9700
C2—H2	0.9300	C30—H30B	0.9700
C3—C4	1.354 (12)	C31—C32	1.347 (8)
C3—H3	0.9300	C31—C36	1.395 (8)
C4—C5	1.431 (9)	C32—C33	1.375 (10)
C4—C6	1.504 (12)	C32—H32	0.9300
C5—C9	1.443 (9)	C33—C34	1.407 (12)
C6—C7	1.338 (14)	C33—H33	0.9300
C6—H6	0.9300	C34—C35	1.340 (11)
C7—C8	1.414 (12)	C34—H34	0.9300
C7—H7	0.9300	C35—C36	1.374 (10)
C8—C10	1.385 (11)	C35—H35	0.9300
C8—C9	1.440 (8)	C36—H36	0.9300
C10—C11	1.350 (11)

O1—Sm1—O2	48.11 (10)	C8—C10—H10	119.7
O1—Sm1—O3	73.35 (12)	C10—C11—C12	118.9 (7)
O1—Sm1—O5	139.14 (12)	C10—C11—H11	120.5
O2—Sm1—O3	65.25 (11)	C12—C11—H11	120.5
O2—Sm1—O5	139.49 (11)	N2—C12—C11	123.2 (7)
O3—Sm1—O5	145.83 (12)	N2—C12—H12	118.4
O1—Sm1—N1	63.68 (12)	C11—C12—H12	118.4
O2—Sm1—N1	102.42 (13)	O4—C13—O3	128.3 (5)
O3—Sm1—N1	127.29 (13)	O4—C13—C14	120.2 (5)
O5—Sm1—N1	77.22 (13)	O3—C13—C14	111.4 (4)
O1—Sm1—N2	74.31 (12)	N3—C14—C13	109.8 (4)
O2—Sm1—N2	118.35 (11)	N3—C14—H14A	109.7
O3—Sm1—N2	80.65 (13)	C13—C14—H14A	109.7
O5—Sm1—N2	96.87 (12)	N3—C14—H14B	109.7
N1—Sm1—N2	60.01 (14)	C13—C14—H14B	109.7
O5—Sm1—O2ⁱ	87.71 (14)	H14A—C14—H14B	108.2
O2ⁱ—Sm1—O3	78.49 (12)	C16—C15—C20	122.1 (6)
O5—Sm1—O4ⁱ	75.58 (12)	C16—C15—N3	114.5 (6)
O2ⁱ—Sm1—O4ⁱ	74.21 (12)	C20—C15—N3	123.4 (6)
O3—Sm1—O4ⁱ	128.43 (12)	C15—C16—C17	119.0 (8)
O5—Sm1—O6ⁱⁱ	77.15 (12)	C15—C16—H16	120.5
O2ⁱ—Sm1—O6ⁱⁱ	78.27 (13)	C17—C16—H16	120.5
O3—Sm1—O6ⁱⁱ	69.53 (12)	C18—C17—C16	120.2 (8)
O4ⁱ—Sm1—O6ⁱⁱ	141.66 (12)	C18—C17—H17	119.9
O2ⁱ—Sm1—O1	120.60 (13)	C16—C17—H17	119.9
O4ⁱ—Sm1—O1	84.19 (12)	C19—C18—C17	121.2 (8)
O6ⁱⁱ—Sm1—O1	133.38 (11)	C19—C18—H18	119.4
O2ⁱ—Sm1—N2	148.76 (14)	C17—C18—H18	119.4
O4ⁱ—Sm1—N2	136.88 (14)	C18—C19—C20	119.2 (9)
O6ⁱⁱ—Sm1—N2	72.75 (14)	C18—C19—H19	120.4
O2ⁱ—Sm1—N1	150.06 (13)	C20—C19—H19	120.4
O4ⁱ—Sm1—N1	77.01 (13)	C15—C20—C19	118.3 (8)
O6ⁱⁱ—Sm1—N1	122.05 (14)	C15—C20—H20	120.8
O2ⁱ—Sm1—O2	72.71 (14)	C19—C20—H20	120.8
O4ⁱ—Sm1—O2	65.20 (11)	O1—C21—O2	122.0 (5)
O6ⁱⁱ—Sm1—O2	129.87 (12)	O1—C21—C22	121.3 (5)
C21—O1—Sm1	102.0 (3)	O2—C21—C22	116.7 (5)
C21—O2—Sm1ⁱ	163.1 (4)	N4—C22—C21	114.5 (5)
C21—O2—Sm1	87.7 (3)	N4—C22—H22A	108.6
Sm1ⁱ—O2—Sm1	107.29 (14)	C21—C22—H22A	108.6
C13—O3—Sm1	130.2 (3)	N4—C22—H22B	108.6
C13—O4—Sm1ⁱ	138.1 (3)	C21—C22—H22B	108.6
C29—O5—Sm1	151.4 (3)	H22A—C22—H22B	107.6
C29—O6—Sm1ⁱⁱ	149.8 (3)	C24—C23—N4	128.4 (13)
C1—N1—C5	119.1 (5)	C24—C23—C28	119.6 (12)
C1—N1—Sm1	119.8 (4)	N4—C23—C28	112.0 (13)
C5—N1—Sm1	119.6 (4)	C23—C24—C25	120.7 (13)
C9—N2—C12	117.8 (5)	C23—C24—H24	119.6
C9—N2—Sm1	121.7 (4)	C25—C24—H24	119.6
C12—N2—Sm1	120.2 (4)	C26—C25—C24	117.7 (14)
C15—N3—C14	117.7 (5)	C26—C25—H25	121.2
C15—N3—H3A	121.2	C24—C25—H25	121.2
C14—N3—H3A	121.2	C25—C26—C27	126.6 (12)
C23—N4—C22	115.1 (8)	C25—C26—H26	116.7
C23—N4—H4	122.4	C27—C26—H26	116.7
C22—N4—H4	122.4	C28—C27—C26	112.5 (12)
C31—N5—C30	118.7 (4)	C28—C27—H27	123.8
C31—N5—H5	120.7	C26—C27—H27	123.8
C30—N5—H5	120.7	C27—C28—C23	122.9 (14)
N1—C1—C2	122.9 (7)	C27—C28—H28	118.6
N1—C1—H1	118.5	C23—C28—H28	118.6
C2—C1—H1	118.5	O6—C29—O5	127.3 (5)
C3—C2—C1	118.4 (7)	O6—C29—C30	119.7 (5)
C3—C2—H2	120.8	O5—C29—C30	112.8 (5)
C1—C2—H2	120.8	N5—C30—C29	111.7 (4)
C4—C3—C2	121.0 (7)	N5—C30—H30A	109.3
C4—C3—H3	119.5	C29—C30—H30A	109.3
C2—C3—H3	119.5	N5—C30—H30B	109.3
C3—C4—C5	117.4 (7)	C29—C30—H30B	109.3
C3—C4—C6	124.6 (8)	H30A—C30—H30B	107.9
C5—C4—C6	118.0 (8)	C32—C31—N5	124.0 (5)
N1—C5—C4	121.2 (6)	C32—C31—C36	120.2 (6)
N1—C5—C9	118.8 (5)	N5—C31—C36	115.8 (6)
C4—C5—C9	120.0 (6)	C31—C32—C33	119.9 (7)
C7—C6—C4	120.6 (8)	C31—C32—H32	120.1
C7—C6—H6	119.7	C33—C32—H32	120.1
C4—C6—H6	119.7	C32—C33—C34	120.2 (8)
C6—C7—C8	121.4 (7)	C32—C33—H33	119.9
C6—C7—H7	119.3	C34—C33—H33	119.9
C8—C7—H7	119.3	C35—C34—C33	118.9 (7)
C10—C8—C7	122.7 (7)	C35—C34—H34	120.5
C10—C8—C9	116.1 (7)	C33—C34—H34	120.5
C7—C8—C9	121.2 (7)	C34—C35—C36	121.2 (7)
N2—C9—C8	123.3 (6)	C34—C35—H35	119.4
N2—C9—C5	118.3 (5)	C36—C35—H35	119.4
C8—C9—C5	118.4 (6)	C35—C36—C31	119.5 (7)
C11—C10—C8	120.5 (6)	C35—C36—H36	120.3
C11—C10—H10	119.7	C31—C36—H36	120.3

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6	0.86	2.32	2.658 (5)	103
N3—H3A···O4	0.86	2.27	2.628 (5)	105
C22—H22B···O5ⁱⁱⁱ	0.97	2.40	3.345 (7)	163
C12—H12···N5ⁱⁱ	0.93	2.60	3.441 (8)	151
C12—H12···O6ⁱⁱ	0.93	2.47	3.059 (8)	121
C10—H10···O1^iv	0.93	2.35	3.218 (7)	156
C1—H1···O4ⁱ	0.93	2.41	3.108 (8)	132

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

Experimental details

Crystal data
Chemical formula	[Sm₂(C₈H₈NO₂)₆(C₁₂H₈N₂)₂]
M_r	1562.04
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	19.998 (3), 8.498 (2), 20.783 (2)
β (°)	106.998 (5)
V (Å³)	3377.7 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.79
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEX II area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.590, 0.871
No. of measured, independent and observed [I > 2σ(I)] reflections	27195, 7519, 4974
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.152, 0.98
No. of reflections	7519
No. of parameters	403
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.54, −0.81

Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Selected geometric parameters (Å, º) top

Sm1—O1	2.559 (3)	Sm1—O5	2.414 (3)
Sm1—O2	2.822 (4)	Sm1—O6ⁱⁱ	2.537 (4)
Sm1—O2ⁱ	2.421 (4)	Sm1—N1	2.728 (4)
Sm1—O3	2.480 (3)	Sm1—N2	2.710 (4)
Sm1—O4ⁱ	2.533 (3)

O1—Sm1—O2	48.11 (10)	O3—Sm1—N1	127.29 (13)
O1—Sm1—O3	73.35 (12)	O5—Sm1—N1	77.22 (13)
O1—Sm1—O5	139.14 (12)	O1—Sm1—N2	74.31 (12)
O2—Sm1—O3	65.25 (11)	O2—Sm1—N2	118.35 (11)
O2—Sm1—O5	139.49 (11)	O3—Sm1—N2	80.65 (13)
O3—Sm1—O5	145.83 (12)	O5—Sm1—N2	96.87 (12)
O1—Sm1—N1	63.68 (12)	N1—Sm1—N2	60.01 (14)
O2—Sm1—N1	102.42 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O6	0.86	2.32	2.658 (5)	103
N3—H3A···O4	0.86	2.27	2.628 (5)	105
C22—H22B···O5ⁱⁱⁱ	0.97	2.40	3.345 (7)	163
C12—H12···N5ⁱⁱ	0.93	2.60	3.441 (8)	151
C12—H12···O6ⁱⁱ	0.93	2.47	3.059 (8)	121
C10—H10···O1^iv	0.93	2.35	3.218 (7)	156
C1—H1···O4ⁱ	0.93	2.41	3.108 (8)	132

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

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Retracted: catena-Poly[[bis­(μ-anilinoacetato-κ2O:O′)bis­(μ-anilinoacetato-κ3O,O′:O)bis­[(1,10-phenanthroline-κ2N,N′)samar­ium(III)]-μ-anilinoacetato-κ2O:O′]