Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807049203/at2419sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807049203/at2419Isup2.hkl |
CCDC reference: 649519
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.019 Å
- R factor = 0.062
- wR factor = 0.133
- Data-to-parameter ratio = 13.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N3 PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 19 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 35.00 A 3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Sm1 (3) 3.52
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
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 me thanol, and a solution of Sm(NO3)3.6H2O (0.364 g, 1 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.
The space group was uniquely assigned from the systematic absences. All H atoms were located in difference Fourier maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å (aryl, formyl), 0.97 Å (methylene) and 0.96 Å (methyl), and with Uiso(H) = 1.2Ueq(C) (aryl, formyl, methylene) or 1.5 Ueq(C) (methyl).
As part of our ongoing research into the complexes between rare earth elements and naphthalene-1-acetato (NNA) and 1,10-phenanthroline (phen) ligands, we have recently reported the crystal structures of forth complexes [Eu(NAA)3(phen)]2.2DMF (II), [Gd(NAA)3(phen)]2.2DMF (III) (Liu et al., 2007a,b), [Pr(NAA)3(phen)]2.DMF and [Tb(NAA)3(phen)]2.2DMF (IV) (Xia, Liu, Wang & Chen, 2007; Xia, Liu, Wang & Yang, 2007). We repot here a similar structure of Hexakis(µ-naphthalene-1-acetato)bis- [(1,10-phenanthroline)samarium(III)] N,N-dimethylformamide disolvate, (I) (Fig. 1).
In the title complex, the coordination environment of Sm atom and coordination modes of the NNA ligands coordinated to the SmIII ion are in agreement with the complex (II), (III) and (IV) (Fig. 1). The average bond lengths of between the samarium center and carboxylic oxygen atoms are 2.456 (7) Å, shorter than that (2.4725 (5) Å) of complex (II), longer than that 2.441 (7) of complex (III) and that 2.450 (7) of complex (IV). The dihedral angles between the least-square-plane Sm2O2 and naphthyl rings are 58.11 (12)° (C3–C12 ring), 43.96 (18)° (C15–C24 ring) and 71.06 (15)° (C27–C36 ring), and the dihedral angle between Sm2O2 plane and phen ring is 81.45 (12)°.
In (I), the molecules are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction with R44(30) rings (Bernstein et al., 1995) surrounds an R22(14) ring centred at (n, 1/2, 1) (n = zero or integer) (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.
Cg1 is the centroid of the C3–C8 ring.
For related literature, see: Bernstein et al. (1995); Liu et al. (2007a,b); Xia, Liu, Wang & Chen (2007); Xia, Liu, Wang & Yang (2007).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
[Sm2(C12H9O2)6(C12H8N2)2]·2C3H7NO | F(000) = 1948 |
Mr = 1918.45 | Dx = 1.453 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3404 reflections |
a = 13.4961 (17) Å | θ = 2.4–25.3° |
b = 15.096 (2) Å | µ = 1.40 mm−1 |
c = 22.150 (2) Å | T = 298 K |
β = 103.720 (2)° | Block, colourless |
V = 4384.0 (10) Å3 | 0.43 × 0.13 × 0.10 mm |
Z = 2 |
Siemens SMART 1000 CCD area-detector diffractometer | 7486 independent reflections |
Radiation source: fine-focus sealed tube | 3943 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.083 |
φ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→16 |
Tmin = 0.585, Tmax = 0.873 | k = −17→17 |
19845 measured reflections | l = −21→26 |
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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + 31.99P] where P = (Fo2 + 2Fc2)/3 |
7486 reflections | (Δ/σ)max = 0.001 |
559 parameters | Δρmax = 1.07 e Å−3 |
0 restraints | Δρmin = −1.39 e Å−3 |
[Sm2(C12H9O2)6(C12H8N2)2]·2C3H7NO | V = 4384.0 (10) Å3 |
Mr = 1918.45 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.4961 (17) Å | µ = 1.40 mm−1 |
b = 15.096 (2) Å | T = 298 K |
c = 22.150 (2) Å | 0.43 × 0.13 × 0.10 mm |
β = 103.720 (2)° |
Siemens SMART 1000 CCD area-detector diffractometer | 7486 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3943 reflections with I > 2σ(I) |
Tmin = 0.585, Tmax = 0.873 | Rint = 0.083 |
19845 measured reflections |
R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + 31.99P] where P = (Fo2 + 2Fc2)/3 |
7486 reflections | Δρmax = 1.07 e Å−3 |
559 parameters | Δρmin = −1.39 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 | 0.38257 (3) | 0.42941 (3) | 1.01172 (2) | 0.03850 (16) | |
N1 | 0.2294 (6) | 0.4434 (5) | 1.0647 (4) | 0.046 (2) | |
N2 | 0.2116 (5) | 0.3639 (6) | 0.9536 (4) | 0.052 (2) | |
N3 | 0.3672 (11) | 0.3362 (9) | 0.2530 (6) | 0.097 (4) | |
O1 | 0.4406 (4) | 0.5797 (4) | 0.9790 (3) | 0.0421 (15) | |
O2 | 0.2765 (4) | 0.5553 (4) | 0.9616 (3) | 0.0493 (17) | |
O3 | 0.4038 (4) | 0.4246 (5) | 0.9082 (3) | 0.0488 (16) | |
O4 | 0.5490 (5) | 0.4870 (4) | 0.8964 (3) | 0.0445 (17) | |
O5 | 0.4123 (5) | 0.2716 (4) | 0.9893 (4) | 0.060 (2) | |
O6 | 0.4040 (5) | 0.3033 (5) | 1.0837 (3) | 0.061 (2) | |
O7 | 0.2330 (10) | 0.2449 (9) | 0.2356 (6) | 0.162 (5) | |
C1 | 0.3480 (8) | 0.5986 (7) | 0.9516 (4) | 0.047 (3) | |
C2 | 0.3348 (7) | 0.6731 (7) | 0.9059 (5) | 0.064 (3) | |
H2A | 0.3765 | 0.6611 | 0.8767 | 0.076* | |
H2B | 0.3605 | 0.7268 | 0.9282 | 0.076* | |
C3 | 0.2263 (8) | 0.6899 (8) | 0.8693 (5) | 0.060 (3) | |
C4 | 0.1777 (9) | 0.7626 (8) | 0.8802 (5) | 0.071 (3) | |
H4 | 0.2113 | 0.8020 | 0.9105 | 0.085* | |
C5 | 0.0766 (10) | 0.7825 (9) | 0.8474 (6) | 0.080 (4) | |
H5 | 0.0448 | 0.8342 | 0.8558 | 0.096* | |
C6 | 0.0269 (10) | 0.7249 (10) | 0.8035 (6) | 0.080 (4) | |
H6 | −0.0401 | 0.7366 | 0.7826 | 0.096* | |
C7 | 0.0746 (10) | 0.6487 (10) | 0.7892 (6) | 0.074 (4) | |
C8 | 0.1752 (9) | 0.6295 (9) | 0.8234 (6) | 0.068 (3) | |
C9 | 0.2213 (10) | 0.5514 (9) | 0.8093 (6) | 0.079 (4) | |
H9 | 0.2874 | 0.5379 | 0.8311 | 0.095* | |
C10 | 0.1710 (12) | 0.4948 (10) | 0.7643 (7) | 0.101 (5) | |
H10 | 0.2030 | 0.4437 | 0.7552 | 0.121* | |
C11 | 0.0702 (12) | 0.5144 (11) | 0.7317 (6) | 0.102 (5) | |
H11 | 0.0353 | 0.4755 | 0.7015 | 0.123* | |
C12 | 0.0244 (11) | 0.5892 (10) | 0.7440 (6) | 0.091 (4) | |
H12 | −0.0419 | 0.6015 | 0.7220 | 0.110* | |
C13 | 0.4737 (7) | 0.4361 (7) | 0.8807 (4) | 0.047 (2) | |
C14 | 0.4631 (8) | 0.3846 (7) | 0.8206 (5) | 0.063 (3) | |
H14A | 0.4150 | 0.3368 | 0.8203 | 0.076* | |
H14B | 0.4333 | 0.4238 | 0.7863 | 0.076* | |
C15 | 0.5586 (9) | 0.3455 (8) | 0.8080 (5) | 0.065 (3) | |
C16 | 0.5889 (9) | 0.3721 (8) | 0.7559 (5) | 0.075 (4) | |
H16 | 0.5513 | 0.4143 | 0.7295 | 0.090* | |
C17 | 0.6784 (10) | 0.3346 (9) | 0.7423 (6) | 0.083 (4) | |
H17 | 0.7009 | 0.3548 | 0.7082 | 0.099* | |
C18 | 0.7296 (10) | 0.2710 (9) | 0.7782 (6) | 0.083 (4) | |
H18 | 0.7868 | 0.2465 | 0.7680 | 0.099* | |
C19 | 0.7002 (10) | 0.2398 (9) | 0.8307 (6) | 0.074 (4) | |
C20 | 0.6132 (9) | 0.2797 (8) | 0.8467 (6) | 0.067 (3) | |
C21 | 0.5844 (10) | 0.2474 (9) | 0.8989 (6) | 0.075 (4) | |
H21 | 0.5290 | 0.2729 | 0.9105 | 0.090* | |
C22 | 0.6350 (11) | 0.1795 (9) | 0.9335 (6) | 0.089 (4) | |
H22 | 0.6133 | 0.1584 | 0.9677 | 0.106* | |
C23 | 0.7203 (11) | 0.1415 (9) | 0.9173 (7) | 0.094 (4) | |
H23 | 0.7550 | 0.0953 | 0.9409 | 0.113* | |
C24 | 0.7516 (10) | 0.1709 (9) | 0.8686 (7) | 0.086 (4) | |
H24 | 0.8089 | 0.1455 | 0.8591 | 0.103* | |
C25 | 0.4099 (9) | 0.2486 (8) | 1.0423 (7) | 0.068 (3) | |
C26 | 0.4134 (9) | 0.1489 (8) | 1.0564 (6) | 0.079 (4) | |
H26A | 0.4801 | 0.1258 | 1.0553 | 0.095* | |
H26B | 0.4035 | 0.1395 | 1.0979 | 0.095* | |
C27 | 0.3334 (12) | 0.0998 (9) | 1.0106 (7) | 0.086 (4) | |
C28 | 0.3594 (12) | 0.0468 (9) | 0.9656 (7) | 0.097 (4) | |
H28 | 0.4272 | 0.0401 | 0.9640 | 0.116* | |
C29 | 0.2805 (15) | 0.0029 (10) | 0.9220 (8) | 0.109 (5) | |
H29 | 0.2975 | −0.0360 | 0.8935 | 0.131* | |
C30 | 0.1813 (15) | 0.0166 (11) | 0.9212 (8) | 0.112 (5) | |
H30 | 0.1315 | −0.0090 | 0.8897 | 0.135* | |
C31 | 0.1520 (14) | 0.0667 (12) | 0.9650 (9) | 0.102 (5) | |
C32 | 0.2301 (13) | 0.1107 (9) | 1.0113 (7) | 0.090 (4) | |
C33 | 0.1993 (11) | 0.1620 (9) | 1.0567 (7) | 0.092 (4) | |
H33 | 0.2485 | 0.1889 | 1.0879 | 0.110* | |
C34 | 0.0965 (12) | 0.1730 (9) | 1.0558 (7) | 0.097 (5) | |
H34 | 0.0768 | 0.2076 | 1.0857 | 0.116* | |
C35 | 0.0237 (13) | 0.1313 (11) | 1.0093 (9) | 0.111 (5) | |
H35 | −0.0449 | 0.1367 | 1.0094 | 0.133* | |
C36 | 0.0496 (14) | 0.0842 (11) | 0.9652 (8) | 0.110 (5) | |
H36 | −0.0017 | 0.0619 | 0.9330 | 0.132* | |
C37 | 0.2354 (8) | 0.4826 (7) | 1.1180 (5) | 0.063 (3) | |
H37 | 0.2986 | 0.5050 | 1.1386 | 0.075* | |
C38 | 0.1539 (9) | 0.4936 (8) | 1.1466 (6) | 0.073 (4) | |
H38 | 0.1631 | 0.5219 | 1.1848 | 0.087* | |
C39 | 0.0609 (9) | 0.4615 (7) | 1.1166 (6) | 0.068 (3) | |
H39 | 0.0053 | 0.4672 | 1.1343 | 0.082* | |
C40 | 0.0497 (8) | 0.4205 (8) | 1.0598 (6) | 0.064 (3) | |
C41 | 0.1359 (8) | 0.4122 (7) | 1.0347 (5) | 0.061 (3) | |
C42 | 0.1273 (8) | 0.3709 (8) | 0.9755 (6) | 0.065 (3) | |
C43 | 0.0312 (9) | 0.3377 (8) | 0.9432 (7) | 0.076 (4) | |
C44 | 0.0264 (10) | 0.2988 (9) | 0.8859 (7) | 0.086 (4) | |
H44 | −0.0356 | 0.2778 | 0.8625 | 0.103* | |
C45 | 0.1104 (10) | 0.2911 (9) | 0.8639 (6) | 0.087 (4) | |
H45 | 0.1071 | 0.2645 | 0.8256 | 0.104* | |
C46 | 0.2031 (9) | 0.3236 (8) | 0.8995 (6) | 0.077 (4) | |
H46 | 0.2614 | 0.3166 | 0.8845 | 0.092* | |
C47 | −0.0459 (9) | 0.3862 (8) | 1.0251 (6) | 0.072 (4) | |
H47 | −0.1033 | 0.3908 | 1.0413 | 0.087* | |
C48 | −0.0539 (9) | 0.3479 (8) | 0.9704 (7) | 0.080 (4) | |
H48 | −0.1173 | 0.3270 | 0.9489 | 0.096* | |
C49 | 0.3091 (15) | 0.2754 (14) | 0.2198 (9) | 0.123 (6) | |
H49 | 0.3249 | 0.2546 | 0.1836 | 0.148* | |
C50 | 0.4569 (11) | 0.3668 (9) | 0.2338 (7) | 0.112 (5) | |
H50A | 0.4696 | 0.3286 | 0.2018 | 0.168* | |
H50B | 0.5147 | 0.3658 | 0.2687 | 0.168* | |
H50C | 0.4458 | 0.4261 | 0.2181 | 0.168* | |
C51 | 0.3411 (13) | 0.3732 (11) | 0.3057 (7) | 0.145 (7) | |
H51A | 0.2716 | 0.3587 | 0.3051 | 0.217* | |
H51B | 0.3487 | 0.4364 | 0.3051 | 0.217* | |
H51C | 0.3852 | 0.3497 | 0.3427 | 0.217* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sm1 | 0.0269 (2) | 0.0437 (3) | 0.0476 (3) | −0.0026 (3) | 0.0142 (2) | −0.0031 (3) |
N1 | 0.039 (5) | 0.049 (5) | 0.057 (5) | 0.004 (4) | 0.022 (4) | 0.007 (4) |
N2 | 0.023 (4) | 0.072 (6) | 0.056 (6) | −0.009 (4) | −0.002 (4) | −0.014 (5) |
N3 | 0.106 (11) | 0.100 (10) | 0.091 (10) | 0.017 (8) | 0.034 (8) | 0.017 (8) |
O1 | 0.032 (3) | 0.044 (4) | 0.054 (4) | −0.005 (3) | 0.018 (3) | −0.001 (3) |
O2 | 0.027 (3) | 0.061 (5) | 0.062 (4) | 0.005 (3) | 0.014 (3) | 0.011 (4) |
O3 | 0.044 (4) | 0.067 (4) | 0.040 (4) | −0.008 (4) | 0.020 (3) | −0.007 (4) |
O4 | 0.036 (4) | 0.056 (4) | 0.043 (4) | −0.011 (3) | 0.012 (3) | −0.010 (3) |
O5 | 0.073 (5) | 0.027 (4) | 0.085 (6) | −0.004 (4) | 0.029 (5) | −0.009 (4) |
O6 | 0.069 (5) | 0.059 (5) | 0.060 (5) | −0.005 (4) | 0.024 (4) | 0.002 (4) |
O7 | 0.123 (10) | 0.177 (13) | 0.181 (13) | −0.013 (9) | 0.026 (9) | 0.053 (10) |
C1 | 0.038 (6) | 0.061 (8) | 0.047 (6) | 0.003 (5) | 0.016 (5) | 0.001 (5) |
C2 | 0.052 (7) | 0.072 (8) | 0.065 (8) | −0.004 (6) | 0.011 (6) | 0.024 (6) |
C3 | 0.051 (7) | 0.071 (9) | 0.058 (8) | 0.003 (7) | 0.011 (6) | 0.023 (7) |
C4 | 0.056 (8) | 0.080 (10) | 0.070 (9) | 0.005 (7) | 0.002 (7) | 0.016 (7) |
C5 | 0.072 (9) | 0.086 (10) | 0.079 (10) | 0.016 (8) | 0.009 (7) | 0.020 (8) |
C6 | 0.064 (9) | 0.096 (11) | 0.074 (10) | 0.008 (8) | 0.005 (7) | 0.026 (8) |
C7 | 0.068 (9) | 0.085 (10) | 0.063 (9) | −0.006 (8) | 0.003 (7) | 0.019 (8) |
C8 | 0.060 (8) | 0.079 (10) | 0.061 (8) | 0.001 (7) | 0.008 (7) | 0.022 (7) |
C9 | 0.074 (9) | 0.086 (11) | 0.067 (9) | 0.004 (8) | −0.002 (7) | 0.011 (8) |
C10 | 0.105 (12) | 0.102 (12) | 0.084 (11) | 0.008 (10) | 0.000 (9) | 0.002 (9) |
C11 | 0.096 (12) | 0.104 (13) | 0.086 (11) | −0.006 (10) | −0.020 (9) | 0.008 (10) |
C12 | 0.084 (10) | 0.100 (13) | 0.079 (10) | −0.004 (9) | −0.003 (8) | 0.019 (9) |
C13 | 0.051 (6) | 0.048 (6) | 0.048 (6) | 0.003 (6) | 0.026 (5) | −0.007 (6) |
C14 | 0.069 (8) | 0.068 (8) | 0.058 (7) | −0.006 (6) | 0.027 (6) | −0.020 (6) |
C15 | 0.073 (8) | 0.070 (9) | 0.063 (8) | −0.003 (7) | 0.036 (7) | −0.023 (7) |
C16 | 0.082 (9) | 0.072 (9) | 0.075 (9) | 0.001 (7) | 0.030 (7) | −0.017 (7) |
C17 | 0.092 (10) | 0.089 (11) | 0.079 (10) | −0.004 (8) | 0.044 (8) | −0.021 (8) |
C18 | 0.081 (10) | 0.086 (11) | 0.088 (11) | −0.001 (8) | 0.033 (9) | −0.029 (8) |
C19 | 0.078 (9) | 0.072 (9) | 0.079 (10) | −0.002 (7) | 0.029 (8) | −0.021 (8) |
C20 | 0.072 (8) | 0.065 (8) | 0.071 (9) | 0.000 (7) | 0.029 (7) | −0.016 (7) |
C21 | 0.078 (9) | 0.073 (9) | 0.077 (9) | 0.003 (7) | 0.024 (8) | −0.012 (7) |
C22 | 0.094 (11) | 0.082 (11) | 0.091 (11) | 0.003 (9) | 0.026 (9) | −0.010 (9) |
C23 | 0.092 (11) | 0.084 (11) | 0.102 (12) | 0.002 (9) | 0.017 (9) | −0.009 (9) |
C24 | 0.084 (10) | 0.082 (11) | 0.094 (11) | 0.001 (8) | 0.027 (9) | −0.023 (9) |
C25 | 0.055 (8) | 0.060 (9) | 0.088 (10) | −0.007 (6) | 0.017 (7) | 0.010 (8) |
C26 | 0.075 (9) | 0.061 (8) | 0.103 (10) | −0.001 (7) | 0.024 (8) | 0.011 (8) |
C27 | 0.098 (12) | 0.061 (9) | 0.101 (12) | −0.005 (8) | 0.025 (10) | 0.010 (8) |
C28 | 0.110 (12) | 0.073 (11) | 0.108 (12) | −0.012 (9) | 0.027 (10) | 0.007 (9) |
C29 | 0.127 (15) | 0.082 (11) | 0.117 (14) | −0.011 (12) | 0.025 (13) | 0.006 (10) |
C30 | 0.123 (16) | 0.085 (13) | 0.119 (15) | −0.020 (12) | 0.009 (13) | 0.015 (11) |
C31 | 0.106 (14) | 0.076 (11) | 0.121 (14) | −0.012 (11) | 0.019 (12) | 0.018 (11) |
C32 | 0.095 (12) | 0.068 (10) | 0.104 (12) | −0.018 (9) | 0.021 (10) | 0.015 (8) |
C33 | 0.087 (11) | 0.073 (10) | 0.117 (13) | −0.011 (8) | 0.025 (10) | 0.010 (9) |
C34 | 0.085 (11) | 0.082 (11) | 0.123 (13) | −0.016 (9) | 0.021 (10) | 0.015 (9) |
C35 | 0.097 (13) | 0.094 (14) | 0.134 (16) | −0.018 (11) | 0.012 (12) | 0.017 (11) |
C36 | 0.108 (15) | 0.088 (13) | 0.125 (15) | −0.020 (11) | 0.011 (12) | 0.012 (11) |
C37 | 0.049 (7) | 0.076 (8) | 0.072 (8) | 0.005 (6) | 0.032 (6) | 0.009 (7) |
C38 | 0.063 (8) | 0.085 (9) | 0.082 (9) | 0.008 (7) | 0.040 (7) | 0.007 (7) |
C39 | 0.057 (8) | 0.070 (9) | 0.089 (10) | 0.009 (6) | 0.040 (7) | 0.016 (7) |
C40 | 0.047 (7) | 0.066 (8) | 0.086 (9) | −0.004 (6) | 0.031 (6) | 0.018 (7) |
C41 | 0.045 (7) | 0.062 (8) | 0.083 (9) | −0.008 (6) | 0.029 (6) | 0.010 (7) |
C42 | 0.046 (7) | 0.069 (8) | 0.084 (10) | −0.010 (6) | 0.024 (7) | 0.007 (7) |
C43 | 0.056 (8) | 0.078 (9) | 0.095 (10) | −0.015 (7) | 0.019 (8) | 0.010 (8) |
C44 | 0.065 (9) | 0.086 (10) | 0.101 (11) | −0.026 (8) | 0.009 (8) | −0.001 (9) |
C45 | 0.070 (9) | 0.095 (11) | 0.091 (10) | −0.024 (8) | 0.009 (8) | −0.012 (8) |
C46 | 0.057 (8) | 0.085 (10) | 0.087 (10) | −0.021 (7) | 0.014 (7) | −0.012 (8) |
C47 | 0.048 (8) | 0.073 (9) | 0.102 (11) | −0.010 (6) | 0.029 (8) | 0.022 (8) |
C48 | 0.053 (8) | 0.082 (10) | 0.106 (11) | −0.021 (7) | 0.018 (8) | 0.015 (9) |
C49 | 0.112 (16) | 0.137 (18) | 0.126 (16) | 0.002 (13) | 0.036 (13) | 0.024 (13) |
C50 | 0.113 (13) | 0.107 (12) | 0.115 (13) | 0.002 (10) | 0.024 (10) | 0.028 (10) |
C51 | 0.177 (18) | 0.146 (16) | 0.125 (15) | 0.038 (13) | 0.062 (13) | −0.004 (12) |
Sm1—O1i | 2.351 (6) | C19—C24 | 1.411 (16) |
Sm1—O3 | 2.379 (5) | C19—C20 | 1.438 (15) |
Sm1—O4i | 2.386 (6) | C20—C21 | 1.393 (15) |
Sm1—O6 | 2.456 (7) | C21—C22 | 1.362 (15) |
Sm1—O2 | 2.478 (6) | C21—H21 | 0.9300 |
Sm1—O5 | 2.486 (6) | C22—C23 | 1.407 (16) |
Sm1—N2 | 2.559 (7) | C22—H22 | 0.9300 |
Sm1—O1 | 2.560 (6) | C23—C24 | 1.325 (16) |
Sm1—N1 | 2.616 (7) | C23—H23 | 0.9300 |
Sm1—Sm1i | 3.9547 (10) | C24—H24 | 0.9300 |
N1—C37 | 1.306 (12) | C25—C26 | 1.536 (15) |
N1—C41 | 1.364 (12) | C26—C27 | 1.491 (16) |
N2—C46 | 1.325 (13) | C26—H26A | 0.9700 |
N2—C42 | 1.342 (12) | C26—H26B | 0.9700 |
N3—C49 | 1.314 (19) | C27—C28 | 1.387 (17) |
N3—C51 | 1.412 (16) | C27—C32 | 1.408 (18) |
N3—C50 | 1.450 (16) | C28—C29 | 1.420 (18) |
O1—C1 | 1.285 (10) | C28—H28 | 0.9300 |
O1—Sm1i | 2.351 (6) | C29—C30 | 1.350 (19) |
O2—C1 | 1.229 (10) | C29—H29 | 0.9300 |
O3—C13 | 1.251 (9) | C30—C31 | 1.36 (2) |
O4—C13 | 1.255 (10) | C30—H30 | 0.9300 |
O4—Sm1i | 2.386 (6) | C31—C36 | 1.41 (2) |
O5—C25 | 1.231 (13) | C31—C32 | 1.446 (19) |
O6—C25 | 1.251 (13) | C32—C33 | 1.408 (17) |
O7—C49 | 1.250 (17) | C33—C34 | 1.392 (16) |
C1—C2 | 1.495 (12) | C33—H33 | 0.9300 |
C2—C3 | 1.517 (13) | C34—C35 | 1.394 (18) |
C2—H2A | 0.9700 | C34—H34 | 0.9300 |
C2—H2B | 0.9700 | C35—C36 | 1.321 (19) |
C3—C4 | 1.330 (14) | C35—H35 | 0.9300 |
C3—C8 | 1.419 (15) | C36—H36 | 0.9300 |
C4—C5 | 1.418 (14) | C37—C38 | 1.404 (13) |
C4—H4 | 0.9300 | C37—H37 | 0.9300 |
C5—C6 | 1.357 (16) | C38—C39 | 1.363 (14) |
C5—H5 | 0.9300 | C38—H38 | 0.9300 |
C6—C7 | 1.391 (16) | C39—C40 | 1.376 (14) |
C6—H6 | 0.9300 | C39—H39 | 0.9300 |
C7—C12 | 1.395 (16) | C40—C41 | 1.409 (13) |
C7—C8 | 1.419 (15) | C40—C47 | 1.434 (14) |
C8—C9 | 1.403 (15) | C41—C42 | 1.432 (14) |
C9—C10 | 1.364 (16) | C42—C43 | 1.417 (15) |
C9—H9 | 0.9300 | C43—C44 | 1.385 (16) |
C10—C11 | 1.413 (17) | C43—C48 | 1.427 (16) |
C10—H10 | 0.9300 | C44—C45 | 1.340 (16) |
C11—C12 | 1.346 (17) | C44—H44 | 0.9300 |
C11—H11 | 0.9300 | C45—C46 | 1.401 (14) |
C12—H12 | 0.9300 | C45—H45 | 0.9300 |
C13—C14 | 1.519 (12) | C46—H46 | 0.9300 |
C14—C15 | 1.503 (13) | C47—C48 | 1.323 (15) |
C14—H14A | 0.9700 | C47—H47 | 0.9300 |
C14—H14B | 0.9700 | C48—H48 | 0.9300 |
C15—C16 | 1.373 (14) | C49—H49 | 0.9300 |
C15—C20 | 1.400 (15) | C50—H50A | 0.9600 |
C16—C17 | 1.428 (15) | C50—H50B | 0.9600 |
C16—H16 | 0.9300 | C50—H50C | 0.9600 |
C17—C18 | 1.332 (16) | C51—H51A | 0.9600 |
C17—H17 | 0.9300 | C51—H51B | 0.9600 |
C18—C19 | 1.395 (16) | C51—H51C | 0.9600 |
C18—H18 | 0.9300 | ||
O1i—Sm1—O3 | 74.35 (19) | C17—C16—H16 | 120.1 |
O1i—Sm1—O4i | 77.1 (2) | C18—C17—C16 | 120.3 (13) |
O3—Sm1—O4i | 136.7 (2) | C18—C17—H17 | 119.8 |
O1i—Sm1—O6 | 86.4 (2) | C16—C17—H17 | 119.8 |
O3—Sm1—O6 | 125.4 (2) | C17—C18—C19 | 122.1 (13) |
O4i—Sm1—O6 | 83.9 (2) | C17—C18—H18 | 119.0 |
O1i—Sm1—O2 | 123.4 (2) | C19—C18—H18 | 119.0 |
O3—Sm1—O2 | 77.3 (2) | C18—C19—C24 | 123.2 (13) |
O4i—Sm1—O2 | 92.4 (2) | C18—C19—C20 | 118.3 (13) |
O6—Sm1—O2 | 148.4 (2) | C24—C19—C20 | 118.5 (13) |
O1i—Sm1—O5 | 75.7 (2) | C21—C20—C15 | 123.2 (11) |
O3—Sm1—O5 | 73.5 (3) | C21—C20—C19 | 117.5 (12) |
O4i—Sm1—O5 | 129.0 (2) | C15—C20—C19 | 119.2 (12) |
O6—Sm1—O5 | 52.2 (2) | C22—C21—C20 | 122.0 (13) |
O2—Sm1—O5 | 138.5 (2) | C22—C21—H21 | 119.0 |
O1i—Sm1—N2 | 142.8 (2) | C20—C21—H21 | 119.0 |
O3—Sm1—N2 | 78.7 (2) | C21—C22—C23 | 119.6 (14) |
O4i—Sm1—N2 | 138.9 (2) | C21—C22—H22 | 120.2 |
O6—Sm1—N2 | 88.9 (3) | C23—C22—H22 | 120.2 |
O2—Sm1—N2 | 73.4 (2) | C24—C23—C22 | 120.7 (15) |
O5—Sm1—N2 | 72.4 (3) | C24—C23—H23 | 119.7 |
O1i—Sm1—O1 | 72.8 (2) | C22—C23—H23 | 119.7 |
O3—Sm1—O1 | 68.9 (2) | C23—C24—C19 | 121.6 (14) |
O4i—Sm1—O1 | 71.9 (2) | C23—C24—H24 | 119.2 |
O6—Sm1—O1 | 150.9 (2) | C19—C24—H24 | 119.2 |
O2—Sm1—O1 | 51.43 (19) | O5—C25—O6 | 122.3 (12) |
O5—Sm1—O1 | 135.9 (2) | O5—C25—C26 | 117.6 (12) |
N2—Sm1—O1 | 120.0 (2) | O6—C25—C26 | 120.1 (12) |
O1i—Sm1—N1 | 149.3 (2) | C27—C26—C25 | 111.5 (11) |
O3—Sm1—N1 | 136.4 (2) | C27—C26—H26A | 109.3 |
O4i—Sm1—N1 | 76.2 (2) | C25—C26—H26A | 109.3 |
O6—Sm1—N1 | 75.8 (2) | C27—C26—H26B | 109.3 |
O2—Sm1—N1 | 72.8 (2) | C25—C26—H26B | 109.3 |
O5—Sm1—N1 | 110.4 (2) | H26A—C26—H26B | 108.0 |
N2—Sm1—N1 | 62.8 (3) | C28—C27—C32 | 119.7 (15) |
O1—Sm1—N1 | 112.5 (2) | C28—C27—C26 | 120.6 (15) |
O1i—Sm1—Sm1i | 38.21 (15) | C32—C27—C26 | 119.6 (14) |
O3—Sm1—Sm1i | 66.81 (15) | C27—C28—C29 | 118.8 (15) |
O4i—Sm1—Sm1i | 70.53 (14) | C27—C28—H28 | 120.6 |
O6—Sm1—Sm1i | 121.89 (17) | C29—C28—H28 | 120.6 |
O2—Sm1—Sm1i | 85.64 (14) | C30—C29—C28 | 121.3 (17) |
O5—Sm1—Sm1i | 108.53 (16) | C30—C29—H29 | 119.4 |
N2—Sm1—Sm1i | 142.88 (19) | C28—C29—H29 | 119.4 |
O1—Sm1—Sm1i | 34.61 (13) | C29—C30—C31 | 122.0 (18) |
N1—Sm1—Sm1i | 139.33 (19) | C29—C30—H30 | 119.0 |
C37—N1—C41 | 116.6 (9) | C31—C30—H30 | 119.0 |
C37—N1—Sm1 | 123.8 (7) | C30—C31—C36 | 123.9 (19) |
C41—N1—Sm1 | 119.5 (7) | C30—C31—C32 | 118.3 (17) |
C46—N2—C42 | 117.7 (9) | C36—C31—C32 | 117.6 (18) |
C46—N2—Sm1 | 120.4 (7) | C27—C32—C33 | 122.2 (15) |
C42—N2—Sm1 | 121.9 (7) | C27—C32—C31 | 119.7 (16) |
C49—N3—C51 | 120.4 (16) | C33—C32—C31 | 118.1 (16) |
C49—N3—C50 | 119.1 (15) | C34—C33—C32 | 121.1 (15) |
C51—N3—C50 | 120.4 (15) | C34—C33—H33 | 119.5 |
C1—O1—Sm1i | 155.2 (6) | C32—C33—H33 | 119.5 |
C1—O1—Sm1 | 90.1 (5) | C33—C34—C35 | 118.9 (16) |
Sm1i—O1—Sm1 | 107.2 (2) | C33—C34—H34 | 120.6 |
C1—O2—Sm1 | 95.4 (6) | C35—C34—H34 | 120.6 |
C13—O3—Sm1 | 138.0 (6) | C36—C35—C34 | 121.7 (18) |
C13—O4—Sm1i | 133.2 (6) | C36—C35—H35 | 119.1 |
C25—O5—Sm1 | 92.1 (7) | C34—C35—H35 | 119.1 |
C25—O6—Sm1 | 93.1 (7) | C35—C36—C31 | 122.3 (19) |
O2—C1—O1 | 120.9 (9) | C35—C36—H36 | 118.8 |
O2—C1—C2 | 123.3 (9) | C31—C36—H36 | 118.8 |
O1—C1—C2 | 115.7 (9) | N1—C37—C38 | 125.1 (11) |
C1—C2—C3 | 115.7 (9) | N1—C37—H37 | 117.5 |
C1—C2—H2A | 108.4 | C38—C37—H37 | 117.5 |
C3—C2—H2A | 108.4 | C39—C38—C37 | 117.9 (12) |
C1—C2—H2B | 108.4 | C39—C38—H38 | 121.1 |
C3—C2—H2B | 108.4 | C37—C38—H38 | 121.1 |
H2A—C2—H2B | 107.4 | C38—C39—C40 | 119.6 (10) |
C4—C3—C8 | 118.9 (11) | C38—C39—H39 | 120.2 |
C4—C3—C2 | 119.8 (12) | C40—C39—H39 | 120.2 |
C8—C3—C2 | 121.3 (11) | C39—C40—C41 | 118.6 (11) |
C3—C4—C5 | 122.6 (13) | C39—C40—C47 | 122.8 (11) |
C3—C4—H4 | 118.7 | C41—C40—C47 | 118.5 (12) |
C5—C4—H4 | 118.7 | N1—C41—C40 | 122.2 (11) |
C6—C5—C4 | 118.9 (13) | N1—C41—C42 | 117.4 (9) |
C6—C5—H5 | 120.5 | C40—C41—C42 | 120.4 (11) |
C4—C5—H5 | 120.5 | N2—C42—C43 | 122.8 (11) |
C5—C6—C7 | 121.1 (13) | N2—C42—C41 | 118.3 (10) |
C5—C6—H6 | 119.5 | C43—C42—C41 | 118.8 (11) |
C7—C6—H6 | 119.5 | C44—C43—C42 | 116.8 (12) |
C6—C7—C12 | 121.6 (13) | C44—C43—C48 | 124.5 (13) |
C6—C7—C8 | 119.0 (13) | C42—C43—C48 | 118.7 (13) |
C12—C7—C8 | 119.4 (14) | C45—C44—C43 | 120.7 (13) |
C9—C8—C7 | 118.2 (13) | C45—C44—H44 | 119.7 |
C9—C8—C3 | 122.3 (12) | C43—C44—H44 | 119.7 |
C7—C8—C3 | 119.5 (13) | C44—C45—C46 | 119.0 (13) |
C10—C9—C8 | 121.2 (13) | C44—C45—H45 | 120.5 |
C10—C9—H9 | 119.4 | C46—C45—H45 | 120.5 |
C8—C9—H9 | 119.4 | N2—C46—C45 | 122.9 (11) |
C9—C10—C11 | 119.7 (14) | N2—C46—H46 | 118.5 |
C9—C10—H10 | 120.2 | C45—C46—H46 | 118.5 |
C11—C10—H10 | 120.2 | C48—C47—C40 | 121.1 (11) |
C12—C11—C10 | 120.3 (15) | C48—C47—H47 | 119.4 |
C12—C11—H11 | 119.8 | C40—C47—H47 | 119.4 |
C10—C11—H11 | 119.8 | C47—C48—C43 | 122.3 (12) |
C11—C12—C7 | 121.2 (14) | C47—C48—H48 | 118.8 |
C11—C12—H12 | 119.4 | C43—C48—H48 | 118.8 |
C7—C12—H12 | 119.4 | O7—C49—N3 | 121 (2) |
O3—C13—O4 | 127.1 (9) | O7—C49—H49 | 119.3 |
O3—C13—C14 | 115.5 (9) | N3—C49—H49 | 119.3 |
O4—C13—C14 | 117.3 (8) | N3—C50—H50A | 109.5 |
C15—C14—C13 | 117.1 (9) | N3—C50—H50B | 109.5 |
C15—C14—H14A | 108.0 | H50A—C50—H50B | 109.5 |
C13—C14—H14A | 108.0 | N3—C50—H50C | 109.5 |
C15—C14—H14B | 108.0 | H50A—C50—H50C | 109.5 |
C13—C14—H14B | 108.0 | H50B—C50—H50C | 109.5 |
H14A—C14—H14B | 107.3 | N3—C51—H51A | 109.5 |
C16—C15—C20 | 120.2 (11) | N3—C51—H51B | 109.5 |
C16—C15—C14 | 118.7 (12) | H51A—C51—H51B | 109.5 |
C20—C15—C14 | 121.0 (10) | N3—C51—H51C | 109.5 |
C15—C16—C17 | 119.8 (12) | H51A—C51—H51C | 109.5 |
C15—C16—H16 | 120.1 | H51B—C51—H51C | 109.5 |
O1i—Sm1—N1—C37 | 28.3 (10) | C4—C3—C8—C9 | −180.0 (11) |
O3—Sm1—N1—C37 | −148.2 (7) | C2—C3—C8—C9 | 0.1 (17) |
O4i—Sm1—N1—C37 | −2.2 (8) | C4—C3—C8—C7 | 1.4 (16) |
O6—Sm1—N1—C37 | 84.9 (8) | C2—C3—C8—C7 | −178.5 (9) |
O2—Sm1—N1—C37 | −99.2 (8) | C7—C8—C9—C10 | −0.4 (18) |
O5—Sm1—N1—C37 | 124.6 (8) | C3—C8—C9—C10 | −179.1 (12) |
N2—Sm1—N1—C37 | −179.0 (9) | C8—C9—C10—C11 | −1 (2) |
O1—Sm1—N1—C37 | −65.7 (8) | C9—C10—C11—C12 | 1 (2) |
Sm1i—Sm1—N1—C37 | −38.0 (9) | C10—C11—C12—C7 | 0 (2) |
O1i—Sm1—N1—C41 | −154.8 (7) | C6—C7—C12—C11 | −178.2 (13) |
O3—Sm1—N1—C41 | 28.7 (9) | C8—C7—C12—C11 | −1 (2) |
O4i—Sm1—N1—C41 | 174.6 (8) | Sm1—O3—C13—O4 | −30.4 (17) |
O6—Sm1—N1—C41 | −98.3 (7) | Sm1—O3—C13—C14 | 151.9 (7) |
O2—Sm1—N1—C41 | 77.7 (7) | Sm1i—O4—C13—O3 | 10.6 (16) |
O5—Sm1—N1—C41 | −58.5 (8) | Sm1i—O4—C13—C14 | −171.8 (6) |
N2—Sm1—N1—C41 | −2.1 (7) | O3—C13—C14—C15 | −140.4 (10) |
O1—Sm1—N1—C41 | 111.2 (7) | O4—C13—C14—C15 | 41.7 (14) |
Sm1i—Sm1—N1—C41 | 138.9 (6) | C13—C14—C15—C16 | −119.5 (11) |
O1i—Sm1—N2—C46 | −21.8 (11) | C13—C14—C15—C20 | 63.9 (14) |
O3—Sm1—N2—C46 | 22.2 (8) | C20—C15—C16—C17 | −2.2 (17) |
O4i—Sm1—N2—C46 | 176.3 (7) | C14—C15—C16—C17 | −178.8 (10) |
O6—Sm1—N2—C46 | −104.3 (9) | C15—C16—C17—C18 | 3.4 (19) |
O2—Sm1—N2—C46 | 102.2 (9) | C16—C17—C18—C19 | −1 (2) |
O5—Sm1—N2—C46 | −53.9 (8) | C17—C18—C19—C24 | 178.3 (13) |
O1—Sm1—N2—C46 | 79.5 (9) | C17—C18—C19—C20 | −1.5 (19) |
N1—Sm1—N2—C46 | −179.0 (9) | C16—C15—C20—C21 | −177.5 (11) |
Sm1i—Sm1—N2—C46 | 43.8 (10) | C14—C15—C20—C21 | −0.9 (18) |
O1i—Sm1—N2—C42 | 160.0 (7) | C16—C15—C20—C19 | −0.8 (17) |
O3—Sm1—N2—C42 | −156.0 (8) | C14—C15—C20—C19 | 175.8 (10) |
O4i—Sm1—N2—C42 | −1.9 (10) | C18—C19—C20—C21 | 179.5 (11) |
O6—Sm1—N2—C42 | 77.5 (8) | C24—C19—C20—C21 | −0.3 (17) |
O2—Sm1—N2—C42 | −76.0 (8) | C18—C19—C20—C15 | 2.6 (17) |
O5—Sm1—N2—C42 | 127.9 (9) | C24—C19—C20—C15 | −177.2 (11) |
O1—Sm1—N2—C42 | −98.7 (8) | C15—C20—C21—C22 | 175.8 (12) |
N1—Sm1—N2—C42 | 2.8 (8) | C19—C20—C21—C22 | −1.0 (18) |
Sm1i—Sm1—N2—C42 | −134.4 (7) | C20—C21—C22—C23 | 1 (2) |
O1i—Sm1—O1—C1 | 161.9 (6) | C21—C22—C23—C24 | 0 (2) |
O3—Sm1—O1—C1 | 82.4 (5) | C22—C23—C24—C19 | −1 (2) |
O4i—Sm1—O1—C1 | −116.5 (5) | C18—C19—C24—C23 | −178.4 (13) |
O6—Sm1—O1—C1 | −151.9 (6) | C20—C19—C24—C23 | 1 (2) |
O2—Sm1—O1—C1 | −8.0 (5) | Sm1—O5—C25—O6 | −5.8 (12) |
O5—Sm1—O1—C1 | 115.6 (5) | Sm1—O5—C25—C26 | 173.6 (9) |
N2—Sm1—O1—C1 | 20.2 (6) | Sm1—O6—C25—O5 | 5.9 (12) |
N1—Sm1—O1—C1 | −50.4 (5) | Sm1—O6—C25—C26 | −173.5 (10) |
Sm1i—Sm1—O1—C1 | 161.9 (6) | O5—C25—C26—C27 | −52.8 (16) |
O1i—Sm1—O1—Sm1i | 0.0 | O6—C25—C26—C27 | 126.7 (13) |
O3—Sm1—O1—Sm1i | −79.4 (2) | C25—C26—C27—C28 | 107.0 (14) |
O4i—Sm1—O1—Sm1i | 81.7 (2) | C25—C26—C27—C32 | −70.1 (16) |
O6—Sm1—O1—Sm1i | 46.2 (5) | C32—C27—C28—C29 | −1.5 (19) |
O2—Sm1—O1—Sm1i | −169.9 (3) | C26—C27—C28—C29 | −178.5 (12) |
O5—Sm1—O1—Sm1i | −46.2 (4) | C27—C28—C29—C30 | 4 (2) |
N2—Sm1—O1—Sm1i | −141.7 (3) | C28—C29—C30—C31 | −6 (2) |
N1—Sm1—O1—Sm1i | 147.7 (2) | C29—C30—C31—C36 | 178.6 (15) |
O1i—Sm1—O2—C1 | −3.2 (6) | C29—C30—C31—C32 | 4 (2) |
O3—Sm1—O2—C1 | −64.5 (6) | C28—C27—C32—C33 | 178.5 (12) |
O4i—Sm1—O2—C1 | 72.9 (6) | C26—C27—C32—C33 | −4.4 (19) |
O6—Sm1—O2—C1 | 155.2 (6) | C28—C27—C32—C31 | 0 (2) |
O5—Sm1—O2—C1 | −110.6 (6) | C26—C27—C32—C31 | 176.9 (12) |
N2—Sm1—O2—C1 | −146.3 (6) | C30—C31—C32—C27 | −1 (2) |
O1—Sm1—O2—C1 | 8.4 (5) | C36—C31—C32—C27 | −175.9 (13) |
N1—Sm1—O2—C1 | 147.7 (6) | C30—C31—C32—C33 | −179.7 (14) |
Sm1i—Sm1—O2—C1 | 2.6 (5) | C36—C31—C32—C33 | 5 (2) |
O1i—Sm1—O3—C13 | −17.0 (10) | C27—C32—C33—C34 | 178.8 (12) |
O4i—Sm1—O3—C13 | 33.6 (11) | C31—C32—C33—C34 | −3 (2) |
O6—Sm1—O3—C13 | −90.7 (10) | C32—C33—C34—C35 | 1 (2) |
O2—Sm1—O3—C13 | 113.6 (10) | C33—C34—C35—C36 | −2 (2) |
O5—Sm1—O3—C13 | −96.3 (10) | C34—C35—C36—C31 | 6 (3) |
N2—Sm1—O3—C13 | −171.1 (10) | C30—C31—C36—C35 | 178.3 (16) |
O1—Sm1—O3—C13 | 60.3 (10) | C32—C31—C36—C35 | −7 (2) |
N1—Sm1—O3—C13 | 161.2 (9) | C41—N1—C37—C38 | 0.9 (16) |
Sm1i—Sm1—O3—C13 | 22.9 (10) | Sm1—N1—C37—C38 | 177.9 (8) |
O1i—Sm1—O5—C25 | 99.8 (7) | N1—C37—C38—C39 | −0.4 (17) |
O3—Sm1—O5—C25 | 177.4 (7) | C37—C38—C39—C40 | −0.5 (17) |
O4i—Sm1—O5—C25 | 40.0 (8) | C38—C39—C40—C41 | 0.7 (17) |
O6—Sm1—O5—C25 | 3.2 (7) | C38—C39—C40—C47 | −179.1 (11) |
O2—Sm1—O5—C25 | −135.4 (7) | C37—N1—C41—C40 | −0.7 (15) |
N2—Sm1—O5—C25 | −99.5 (7) | Sm1—N1—C41—C40 | −177.7 (8) |
O1—Sm1—O5—C25 | 145.2 (6) | C37—N1—C41—C42 | 178.6 (10) |
N1—Sm1—O5—C25 | −48.5 (7) | Sm1—N1—C41—C42 | 1.5 (13) |
Sm1i—Sm1—O5—C25 | 119.6 (7) | C39—C40—C41—N1 | −0.2 (17) |
O1i—Sm1—O6—C25 | −77.7 (7) | C47—C40—C41—N1 | 179.7 (10) |
O3—Sm1—O6—C25 | −9.9 (7) | C39—C40—C41—C42 | −179.4 (11) |
O4i—Sm1—O6—C25 | −155.1 (7) | C47—C40—C41—C42 | 0.5 (16) |
O2—Sm1—O6—C25 | 120.1 (7) | C46—N2—C42—C43 | −0.4 (17) |
O5—Sm1—O6—C25 | −3.1 (6) | Sm1—N2—C42—C43 | 177.8 (8) |
N2—Sm1—O6—C25 | 65.4 (7) | C46—N2—C42—C41 | 178.4 (10) |
O1—Sm1—O6—C25 | −121.5 (7) | Sm1—N2—C42—C41 | −3.3 (14) |
N1—Sm1—O6—C25 | 127.6 (7) | N1—C41—C42—N2 | 1.1 (16) |
Sm1i—Sm1—O6—C25 | −92.6 (7) | C40—C41—C42—N2 | −179.6 (10) |
Sm1—O2—C1—O1 | −15.4 (9) | N1—C41—C42—C43 | −180.0 (10) |
Sm1—O2—C1—C2 | 162.3 (9) | C40—C41—C42—C43 | −0.7 (17) |
Sm1i—O1—C1—O2 | 149.8 (10) | N2—C42—C43—C44 | −1.6 (18) |
Sm1—O1—C1—O2 | 14.8 (9) | C41—C42—C43—C44 | 179.6 (11) |
Sm1i—O1—C1—C2 | −28 (2) | N2—C42—C43—C48 | 179.7 (11) |
Sm1—O1—C1—C2 | −163.1 (8) | C41—C42—C43—C48 | 0.9 (17) |
O2—C1—C2—C3 | −3.1 (15) | C42—C43—C44—C45 | 2 (2) |
O1—C1—C2—C3 | 174.8 (9) | C48—C43—C44—C45 | −179.4 (13) |
C1—C2—C3—C4 | 110.1 (12) | C43—C44—C45—C46 | 0 (2) |
C1—C2—C3—C8 | −69.9 (13) | C42—N2—C46—C45 | 2.1 (18) |
C8—C3—C4—C5 | −0.3 (17) | Sm1—N2—C46—C45 | −176.2 (9) |
C2—C3—C4—C5 | 179.6 (10) | C44—C45—C46—N2 | −2 (2) |
C3—C4—C5—C6 | 0.5 (18) | C39—C40—C47—C48 | 179.4 (12) |
C4—C5—C6—C7 | −1.8 (19) | C41—C40—C47—C48 | −0.5 (18) |
C5—C6—C7—C12 | −179.8 (12) | C40—C47—C48—C43 | 1 (2) |
C5—C6—C7—C8 | 2.9 (18) | C44—C43—C48—C47 | −179.5 (13) |
C6—C7—C8—C9 | 178.6 (11) | C42—C43—C48—C47 | −0.9 (19) |
C12—C7—C8—C9 | 1.3 (17) | C51—N3—C49—O7 | −4 (3) |
C6—C7—C8—C3 | −2.7 (17) | C50—N3—C49—O7 | 177.6 (15) |
C12—C7—C8—C3 | 179.9 (11) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O7ii | 0.93 | 2.55 | 3.438 (18) | 159 |
C37—H37···O4i | 0.93 | 2.37 | 3.036 (12) | 129 |
C46—H46···O3 | 0.93 | 2.48 | 3.074 (13) | 122 |
C47—H47···O2iii | 0.93 | 2.46 | 3.314 (13) | 153 |
C50—H50A···O6iv | 0.96 | 2.58 | 3.369 (16) | 139 |
C18—H18···Cg1v | 0.93 | 2.88 | 3.661 (15) | 143 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Sm2(C12H9O2)6(C12H8N2)2]·2C3H7NO |
Mr | 1918.45 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 13.4961 (17), 15.096 (2), 22.150 (2) |
β (°) | 103.720 (2) |
V (Å3) | 4384.0 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.43 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Siemens SMART 1000 CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.585, 0.873 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19845, 7486, 3943 |
Rint | 0.083 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.133, 1.03 |
No. of reflections | 7486 |
No. of parameters | 559 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + 31.99P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.07, −1.39 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Sm1—O1i | 2.351 (6) | Sm1—O5 | 2.486 (6) |
Sm1—O3 | 2.379 (5) | Sm1—N2 | 2.559 (7) |
Sm1—O4i | 2.386 (6) | Sm1—O1 | 2.560 (6) |
Sm1—O6 | 2.456 (7) | Sm1—N1 | 2.616 (7) |
Sm1—O2 | 2.478 (6) |
Symmetry code: (i) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O7ii | 0.93 | 2.55 | 3.438 (18) | 159.1 |
C37—H37···O4i | 0.93 | 2.37 | 3.036 (12) | 128.7 |
C46—H46···O3 | 0.93 | 2.48 | 3.074 (13) | 121.9 |
C47—H47···O2iii | 0.93 | 2.46 | 3.314 (13) | 152.5 |
C50—H50A···O6iv | 0.96 | 2.58 | 3.369 (16) | 139.3 |
C18—H18···Cg1v | 0.93 | 2.88 | 3.661 (15) | 143 |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) x, y, z−1; (v) −x+1, y+1/2, −z+1/2. |
As part of our ongoing research into the complexes between rare earth elements and naphthalene-1-acetato (NNA) and 1,10-phenanthroline (phen) ligands, we have recently reported the crystal structures of forth complexes [Eu(NAA)3(phen)]2.2DMF (II), [Gd(NAA)3(phen)]2.2DMF (III) (Liu et al., 2007a,b), [Pr(NAA)3(phen)]2.DMF and [Tb(NAA)3(phen)]2.2DMF (IV) (Xia, Liu, Wang & Chen, 2007; Xia, Liu, Wang & Yang, 2007). We repot here a similar structure of Hexakis(µ-naphthalene-1-acetato)bis- [(1,10-phenanthroline)samarium(III)] N,N-dimethylformamide disolvate, (I) (Fig. 1).
In the title complex, the coordination environment of Sm atom and coordination modes of the NNA ligands coordinated to the SmIII ion are in agreement with the complex (II), (III) and (IV) (Fig. 1). The average bond lengths of between the samarium center and carboxylic oxygen atoms are 2.456 (7) Å, shorter than that (2.4725 (5) Å) of complex (II), longer than that 2.441 (7) of complex (III) and that 2.450 (7) of complex (IV). The dihedral angles between the least-square-plane Sm2O2 and naphthyl rings are 58.11 (12)° (C3–C12 ring), 43.96 (18)° (C15–C24 ring) and 71.06 (15)° (C27–C36 ring), and the dihedral angle between Sm2O2 plane and phen ring is 81.45 (12)°.
In (I), the molecules are linked into sheets by means of C—H···π hydrogen bond (Fig. 2 and Table 2) and chains parallel to the a axis direction with R44(30) rings (Bernstein et al., 1995) surrounds an R22(14) ring centred at (n, 1/2, 1) (n = zero or integer) (Fig. 3) by C—H···O hydrogen bonds (Fig. 3 and Table 2). The action of a chains are to link adjacent [100] sheet into the three-dimensional framework structure.
Cg1 is the centroid of the C3–C8 ring.