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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): m1377–m1378.
Published online 2010 October 9. doi:  10.1107/S1600536810037153
PMCID: PMC3009179

Tetra­kis[μ-2-(3,4-dimeth­oxy­phen­yl)acetato]-κ4 O:O′;κ3 O,O′:O3 O:O,O′-bis­{[2-(3,4-dimeth­oxy­phen­yl)acetato-κ2 O,O′](1,10-phenanthroline-κ2 N,N′)samarium(III)}

Abstract

In the centrosymmetric dinuclear title complex, [Sm2(C10H11O4)6(C12H8N2)2], the SmIII ion is nine-coordinated by seven O atoms of five 2-(3,4-dimeth­oxy­phen­yl)acetate (DMPA) ligands and two N atoms of one bis-chelating 1,10-phenanthroline (phen) ligand, forming a distorted tricapped trigonal-prismatic environment. The DMPA ligands coordinate in bis-chelate, bridging and bridging tridentate modes. An intra­molecular C—H(...)O hydrogen bond occurs. Inter­molecular C—H(...)O inter­actions are also present in the crystal.

Related literature

For the importance of coordination chemistry in magnetism, see: Fang & Zhang (2006 [triangle]); Yao et al. (2008 [triangle]); Wang & Sevov (2008 [triangle]). For related structures, see: Li et al. (2008 [triangle]); Liu et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1377-scheme1.jpg

Experimental

Crystal data

  • [Sm2(C10H11O4)6(C12H8N2)2]
  • M r = 1832.26
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1377-efi1.jpg
  • a = 12.3696 (1) Å
  • b = 12.4344 (1) Å
  • c = 14.7467 (1) Å
  • α = 90.641 (1)°
  • β = 103.492 (1)°
  • γ = 116.648 (1)°
  • V = 1953.71 (3) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 1.57 mm−1
  • T = 296 K
  • 0.35 × 0.15 × 0.09 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.757, T max = 0.874
  • 30687 measured reflections
  • 9023 independent reflections
  • 7540 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.102
  • S = 0.76
  • 9023 reflections
  • 514 parameters
  • H-atom parameters constrained
  • Δρmax = 0.80 e Å−3
  • Δρmin = −0.49 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810037153/fk2022sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037153/fk2022Isup2.hkl

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

supplementary crystallographic information

Comment

In recent years, there has been an increasing interest in the coordination chemistry due to the increased recognition of it's importance in magnetism (Yao, et al., 2008; Fang, et al., 2006; Wang, et al., 2008) and antibacterial properties; we have worked in it before (Li, et al., 2008; Liu, et al., 2010). Here we report the crystal structure of a new samariumIII complex with the ligand 3,4-dimethoxylphenyl acetic acid. The title compound consists of two central samariumIII atoms coordinated with six homoveratric acid molecules and two phen molecules. In the bicentric structure, the DMPA ligands coordinate in the bis-chelate, bridging and bridging tridentate modes. Each samarium atom is nine coordinated from seven O atoms from five DMPA molecules and two N atoms from a phen molecule (Fig.1). The samariumIII atom is in a distorted capped square prismatic environment. The Sm—O bond lengths range from 2.397 (2) Å to 2.563 (2) Å and the Sm—N distances range from 2.591 (3) Å to 2.656 (3) Å. Intermolecular interactions (see Table 1) are C—H···O hydrogen bonds and weak π···π aromatic interactions from phen molecules and aromatic rings of the L ligands.

Experimental

All reagents and solvents used were of commercially available quality and without purified before using. The title compound was obtained by adding Sm2O3(0.5 mmol), homoveratric acid (3 mmol) phen (1 mmol) dissolved in 30 ml water, sealed in a 50 ml stainless steel reactor and kept three days at temperature of 433 K. Then the reactor was cooled to room temperature at a speed of 5 K per hour. After filtration of the solution and washing the deposition with ethanol, colorless crystals were obtained.

Refinement

The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C))].

Figures

Fig. 1.
The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

[Sm2(C10H11O4)6(C12H8N2)2]Z = 1
Mr = 1832.26F(000) = 930
Triclinic, P1Dx = 1.557 Mg m3
Hall symbol: -p 1Mo Kα radiation, λ = 0.71073 Å
a = 12.3696 (1) ÅCell parameters from 9931 reflections
b = 12.4344 (1) Åθ = 1.4–27.6°
c = 14.7467 (1) ŵ = 1.57 mm1
α = 90.641 (1)°T = 296 K
β = 103.492 (1)°Block, colourless
γ = 116.648 (1)°0.35 × 0.15 × 0.09 mm
V = 1953.71 (3) Å3

Data collection

Bruker APEXII area-detector diffractometer9023 independent reflections
Radiation source: fine-focus sealed tube7540 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.6°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009h = −16→16
Tmin = 0.757, Tmax = 0.874k = −15→16
30687 measured reflectionsl = −19→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.76w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
9023 reflections(Δ/σ)max = 0.001
514 parametersΔρmax = 0.80 e Å3
0 restraintsΔρmin = −0.49 e Å3

Special details

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)

xyzUiso*/Ueq
Sm1−0.181987 (12)0.388581 (13)0.966794 (9)0.03674 (7)
N1−0.3981 (3)0.3465 (3)0.9898 (2)0.0492 (6)
O1−0.2349 (3)−0.0181 (3)1.4333 (2)0.0785 (9)
C1−0.3117 (6)−0.0058 (5)1.4856 (3)0.0959 (16)
H1A−0.2851−0.01801.54950.144*
H1B−0.3974−0.06511.45840.144*
H1C−0.30490.07421.48460.144*
N2−0.3687 (2)0.3332 (2)0.81292 (19)0.0438 (6)
C2−0.2610 (4)−0.0030 (3)1.3402 (3)0.0565 (9)
O2−0.1033 (3)−0.0586 (3)1.3409 (2)0.0763 (8)
O3−0.2346 (2)0.24081 (19)1.08276 (15)0.0456 (5)
C3−0.3491 (4)0.0293 (4)1.2953 (3)0.0646 (10)
H3A−0.39600.04601.32890.078*
O4−0.2685 (3)0.1685 (2)0.93737 (15)0.0560 (6)
C4−0.3697 (4)0.0374 (4)1.1995 (3)0.0603 (9)
H4A−0.43090.05851.16930.072*
O5−0.3659 (2)0.9419 (2)0.69521 (16)0.0506 (6)
C5−0.3001 (3)0.0143 (3)1.1488 (2)0.0496 (8)
O6−0.3882 (3)0.7370 (2)0.63142 (19)0.0662 (8)
C6−0.2089 (3)−0.0154 (3)1.1954 (2)0.0513 (8)
H6A−0.1600−0.02931.16220.062*
O7−0.01393 (19)0.6002 (2)0.95385 (15)0.0430 (5)
C7−0.1884 (3)−0.0251 (3)1.2902 (3)0.0537 (8)
O8−0.20791 (19)0.5702 (2)0.91159 (16)0.0454 (5)
C8−0.0163 (4)−0.0667 (5)1.2970 (4)0.0873 (15)
H8A0.0377−0.09071.33990.131*
H8B0.03320.01091.27950.131*
H8C−0.0609−0.12591.24180.131*
C9−0.3203 (4)0.0245 (3)1.0452 (3)0.0583 (9)
H9A−0.4096−0.01931.01480.070*
H9B−0.2801−0.01491.01910.070*
O90.1593 (3)0.3222 (3)1.5044 (2)0.0808 (9)
C10−0.2708 (3)0.1535 (3)1.0213 (2)0.0416 (7)
O100.2503 (4)0.5480 (3)1.5625 (3)0.0970 (12)
O11−0.1156 (2)0.5174 (2)1.11307 (15)0.0463 (5)
C110.1067 (6)0.1954 (5)1.4761 (4)0.0946 (17)
H11A0.14560.16081.52240.142*
H11B0.12070.18211.41660.142*
H11C0.01810.15761.47020.142*
C120.1146 (4)0.3845 (4)1.4466 (3)0.0630 (10)
C130.0240 (4)0.3342 (4)1.3610 (3)0.0657 (10)
H13A−0.00940.25191.34050.079*
C14−0.0176 (4)0.4051 (4)1.3056 (3)0.0633 (10)
H14A−0.07820.37021.24850.076*
C150.0310 (3)0.5265 (3)1.3353 (2)0.0483 (7)
C160.1196 (4)0.5780 (4)1.4207 (3)0.0595 (9)
H16A0.15100.65991.44140.071*
C170.1624 (4)0.5066 (4)1.4765 (3)0.0631 (10)
C180.2931 (6)0.6660 (5)1.6030 (4)0.108 (2)
H18A0.35370.68221.66220.161*
H18B0.22380.67581.61280.161*
H18C0.33140.72181.56180.161*
C19−0.0160 (4)0.6028 (4)1.2739 (2)0.0564 (9)
H19A−0.10110.58141.27550.068*
H19B0.03640.68811.29840.068*
C20−0.0131 (3)0.5816 (3)1.1727 (2)0.0437 (7)
C21−0.3324 (4)1.0664 (3)0.7158 (3)0.0589 (9)
H21A−0.39031.08560.67240.088*
H21B−0.24901.11570.70990.088*
H21C−0.33511.08220.77880.088*
C22−0.2914 (3)0.9014 (3)0.7514 (2)0.0414 (6)
C23−0.2108 (3)0.9586 (3)0.8370 (2)0.0523 (8)
H23A−0.20611.02990.86240.063*
C24−0.1356 (4)0.9118 (3)0.8867 (3)0.0580 (9)
H24A−0.08270.95130.94580.070*
C25−0.1372 (3)0.8079 (3)0.8506 (2)0.0461 (7)
C26−0.2253 (3)0.7462 (3)0.7652 (2)0.0430 (7)
H26A−0.23280.67290.74120.052*
C27−0.3006 (3)0.7910 (3)0.7161 (2)0.0404 (6)
C28−0.4229 (5)0.6147 (4)0.6042 (3)0.0784 (14)
H28A−0.48420.58670.54430.118*
H28B−0.45790.56660.65030.118*
H28C−0.35020.60750.59960.118*
C29−0.0443 (3)0.7655 (3)0.8985 (3)0.0548 (9)
H29A0.00740.82000.95630.066*
H29B0.01040.77430.85840.066*
C30−0.0952 (3)0.6370 (3)0.9225 (2)0.0368 (6)
C31−0.4152 (4)0.3464 (4)1.0747 (3)0.0639 (10)
H31A−0.35280.34891.12550.077*
C32−0.5237 (4)0.3425 (4)1.0913 (4)0.0748 (13)
H32A−0.53390.34061.15190.090*
C33−0.6140 (4)0.3416 (4)1.0176 (4)0.0772 (14)
H33A−0.68560.34091.02790.093*
C34−0.5995 (3)0.3415 (3)0.9269 (3)0.0621 (10)
C35−0.6890 (3)0.3424 (4)0.8447 (4)0.0786 (15)
H35A−0.75980.34610.85250.094*
C36−0.6745 (4)0.3382 (4)0.7580 (4)0.0728 (13)
H36A−0.73390.34020.70700.087*
C37−0.5682 (3)0.3307 (3)0.7439 (3)0.0567 (10)
C38−0.5517 (4)0.3200 (3)0.6545 (3)0.0631 (10)
H38A−0.61300.31360.60130.076*
C39−0.4458 (4)0.3189 (3)0.6458 (3)0.0611 (9)
H39A−0.43290.31310.58670.073*
C40−0.3554 (3)0.3268 (3)0.7272 (2)0.0513 (8)
H40A−0.28220.32750.72020.062*
C41−0.4741 (3)0.3349 (3)0.8221 (3)0.0447 (7)
C42−0.4901 (3)0.3408 (3)0.9152 (3)0.0484 (8)
O120.0936 (2)0.6289 (2)1.15752 (15)0.0510 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Sm10.03906 (10)0.05158 (12)0.03811 (10)0.03329 (8)0.01703 (7)0.01837 (7)
N10.0488 (15)0.0539 (16)0.0651 (17)0.0325 (12)0.0322 (13)0.0199 (13)
O10.090 (2)0.111 (3)0.0478 (15)0.0536 (19)0.0266 (14)0.0320 (15)
C10.131 (5)0.122 (4)0.058 (3)0.069 (4)0.045 (3)0.027 (3)
N20.0387 (13)0.0473 (14)0.0554 (15)0.0284 (11)0.0124 (11)0.0135 (12)
C20.061 (2)0.059 (2)0.0487 (19)0.0244 (17)0.0201 (16)0.0199 (16)
O20.0709 (18)0.102 (2)0.0763 (19)0.0536 (17)0.0251 (15)0.0396 (16)
O30.0597 (13)0.0469 (12)0.0419 (11)0.0310 (10)0.0213 (10)0.0136 (9)
C30.074 (2)0.080 (3)0.059 (2)0.045 (2)0.0318 (19)0.0208 (19)
O40.0879 (18)0.0600 (14)0.0364 (11)0.0461 (13)0.0202 (11)0.0164 (10)
C40.068 (2)0.075 (2)0.053 (2)0.045 (2)0.0181 (17)0.0225 (18)
O50.0597 (14)0.0521 (13)0.0489 (12)0.0389 (11)0.0031 (10)0.0108 (10)
C50.0547 (18)0.0403 (17)0.0520 (18)0.0197 (14)0.0154 (15)0.0166 (14)
O60.0804 (18)0.0497 (14)0.0550 (15)0.0353 (13)−0.0162 (13)−0.0021 (11)
C60.0575 (19)0.0453 (18)0.0577 (19)0.0243 (15)0.0254 (16)0.0179 (15)
O70.0450 (11)0.0622 (13)0.0460 (11)0.0416 (10)0.0191 (9)0.0239 (10)
C70.0521 (19)0.053 (2)0.058 (2)0.0245 (15)0.0172 (16)0.0228 (16)
O80.0412 (11)0.0519 (12)0.0590 (13)0.0337 (10)0.0155 (10)0.0204 (10)
C80.063 (3)0.091 (3)0.121 (4)0.047 (3)0.024 (3)0.032 (3)
C90.080 (3)0.054 (2)0.0434 (18)0.0308 (19)0.0204 (17)0.0118 (15)
O90.096 (2)0.082 (2)0.0684 (18)0.0536 (18)0.0025 (16)0.0195 (15)
C100.0421 (15)0.0515 (18)0.0416 (16)0.0304 (14)0.0113 (12)0.0132 (13)
O100.097 (3)0.092 (2)0.086 (2)0.047 (2)−0.010 (2)−0.0098 (19)
O110.0458 (12)0.0621 (14)0.0460 (12)0.0346 (11)0.0188 (10)0.0139 (10)
C110.111 (4)0.081 (3)0.090 (4)0.050 (3)0.012 (3)0.033 (3)
C120.067 (2)0.076 (3)0.054 (2)0.040 (2)0.0149 (17)0.0184 (18)
C130.080 (3)0.063 (2)0.053 (2)0.035 (2)0.0121 (18)0.0099 (17)
C140.074 (2)0.072 (3)0.0454 (18)0.038 (2)0.0099 (17)0.0114 (17)
C150.0489 (17)0.064 (2)0.0435 (16)0.0315 (16)0.0216 (14)0.0143 (14)
C160.057 (2)0.063 (2)0.059 (2)0.0290 (17)0.0156 (17)0.0093 (17)
C170.058 (2)0.082 (3)0.054 (2)0.039 (2)0.0096 (17)0.0145 (19)
C180.095 (4)0.114 (5)0.085 (4)0.043 (3)−0.012 (3)−0.037 (3)
C190.067 (2)0.075 (2)0.0487 (18)0.0458 (19)0.0264 (16)0.0152 (16)
C200.0490 (17)0.0607 (19)0.0416 (16)0.0387 (15)0.0196 (13)0.0193 (14)
C210.077 (2)0.061 (2)0.058 (2)0.051 (2)0.0119 (18)0.0148 (16)
C220.0420 (15)0.0451 (16)0.0468 (16)0.0279 (13)0.0129 (13)0.0136 (13)
C230.065 (2)0.0527 (19)0.0485 (17)0.0414 (17)0.0032 (15)0.0003 (14)
C240.066 (2)0.057 (2)0.0491 (19)0.0392 (18)−0.0101 (16)−0.0028 (15)
C250.0429 (16)0.0466 (17)0.0570 (18)0.0287 (14)0.0105 (14)0.0176 (14)
C260.0544 (17)0.0399 (16)0.0445 (16)0.0301 (14)0.0132 (13)0.0101 (12)
C270.0438 (15)0.0379 (15)0.0408 (15)0.0217 (12)0.0079 (12)0.0091 (12)
C280.091 (3)0.051 (2)0.072 (3)0.032 (2)−0.012 (2)−0.0083 (19)
C290.0419 (17)0.051 (2)0.074 (2)0.0295 (15)0.0028 (16)0.0179 (18)
C300.0440 (15)0.0483 (16)0.0352 (14)0.0344 (13)0.0134 (12)0.0139 (12)
C310.063 (2)0.071 (3)0.077 (3)0.037 (2)0.042 (2)0.021 (2)
C320.080 (3)0.065 (2)0.102 (3)0.033 (2)0.064 (3)0.017 (2)
C330.051 (2)0.057 (2)0.139 (4)0.0272 (18)0.049 (3)0.002 (2)
C340.0412 (17)0.0409 (18)0.111 (3)0.0208 (14)0.0294 (19)0.0022 (19)
C350.0306 (17)0.059 (2)0.148 (5)0.0268 (16)0.014 (2)0.003 (3)
C360.0404 (19)0.058 (2)0.112 (4)0.0266 (17)−0.001 (2)0.001 (2)
C370.0363 (16)0.0342 (16)0.092 (3)0.0176 (13)0.0016 (17)0.0106 (16)
C380.055 (2)0.053 (2)0.069 (2)0.0244 (17)−0.0029 (18)0.0116 (18)
C390.067 (2)0.060 (2)0.057 (2)0.0346 (19)0.0060 (17)0.0135 (17)
C400.0532 (19)0.0536 (19)0.0545 (19)0.0321 (16)0.0118 (15)0.0157 (15)
C410.0350 (14)0.0347 (15)0.067 (2)0.0198 (12)0.0107 (14)0.0103 (14)
C420.0343 (14)0.0346 (15)0.086 (2)0.0215 (12)0.0210 (15)0.0099 (15)
O120.0462 (12)0.0756 (15)0.0424 (11)0.0352 (11)0.0174 (9)0.0122 (11)

Geometric parameters (Å, °)

Sm1—O7i2.373 (2)C12—C131.391 (5)
Sm1—O12i2.397 (2)C13—C141.392 (6)
Sm1—O112.410 (2)C13—H13A0.9300
Sm1—O42.440 (2)C14—C151.372 (5)
Sm1—O32.498 (2)C14—H14A0.9300
Sm1—O82.537 (2)C15—C161.380 (5)
Sm1—O72.564 (2)C15—C191.525 (5)
Sm1—N12.590 (3)C16—C171.407 (6)
Sm1—N22.655 (3)C16—H16A0.9300
Sm1—C102.825 (3)C18—H18A0.9600
Sm1—C302.919 (3)C18—H18B0.9600
Sm1—Sm1i3.9495 (3)C18—H18C0.9600
N1—C311.318 (5)C19—C201.524 (4)
N1—C421.360 (5)C19—H19A0.9700
O1—C21.370 (4)C19—H19B0.9700
O1—C11.411 (6)C20—O121.257 (4)
C1—H1A0.9600C21—H21A0.9600
C1—H1B0.9600C21—H21B0.9600
C1—H1C0.9600C21—H21C0.9600
N2—C401.319 (4)C22—C231.360 (5)
N2—C411.352 (4)C22—C271.409 (4)
C2—C31.360 (6)C23—C241.386 (5)
C2—C71.396 (5)C23—H23A0.9300
O2—C71.369 (4)C24—C251.381 (5)
O2—C81.418 (6)C24—H24A0.9300
O3—C101.246 (4)C25—C261.397 (4)
C3—C41.388 (5)C25—C291.507 (4)
C3—H3A0.9300C26—C271.364 (4)
O4—C101.258 (4)C26—H26A0.9300
C4—C51.379 (5)C28—H28A0.9600
C4—H4A0.9300C28—H28B0.9600
O5—C221.363 (4)C28—H28C0.9600
O5—C211.420 (4)C29—C301.512 (5)
C5—C61.379 (5)C29—H29A0.9700
C5—C91.506 (5)C29—H29B0.9700
O6—C271.372 (4)C31—C321.399 (6)
O6—C281.406 (5)C31—H31A0.9300
C6—C71.378 (5)C32—C331.361 (7)
C6—H6A0.9300C32—H32A0.9300
O7—C301.279 (3)C33—C341.390 (7)
O7—Sm1i2.3731 (19)C33—H33A0.9300
O8—C301.230 (4)C34—C421.407 (4)
C8—H8A0.9600C34—C351.443 (7)
C8—H8B0.9600C35—C361.336 (7)
C8—H8C0.9600C35—H35A0.9300
C9—C101.518 (5)C36—C371.421 (6)
C9—H9A0.9700C36—H36A0.9300
C9—H9B0.9700C37—C381.394 (6)
O9—C121.345 (5)C37—C411.415 (5)
O9—C111.422 (6)C38—C391.351 (6)
O10—C171.377 (5)C38—H38A0.9300
O10—C181.387 (6)C39—C401.405 (5)
O11—C201.255 (4)C39—H39A0.9300
C11—H11A0.9600C40—H40A0.9300
C11—H11B0.9600C41—C421.438 (5)
C11—H11C0.9600O12—Sm1i2.397 (2)
C12—C171.381 (6)
O7i—Sm1—O12i75.89 (7)O4—C10—Sm159.49 (17)
O7i—Sm1—O1175.04 (7)C9—C10—Sm1177.0 (2)
O12i—Sm1—O11137.69 (8)C17—O10—C18118.7 (4)
O7i—Sm1—O488.68 (8)C20—O11—Sm1135.8 (2)
O12i—Sm1—O479.61 (8)O9—C11—H11A109.5
O11—Sm1—O4129.32 (7)O9—C11—H11B109.5
O7i—Sm1—O375.96 (7)H11A—C11—H11B109.5
O12i—Sm1—O3124.10 (8)O9—C11—H11C109.5
O11—Sm1—O376.85 (7)H11A—C11—H11C109.5
O4—Sm1—O352.55 (7)H11B—C11—H11C109.5
O7i—Sm1—O8123.58 (7)O9—C12—C17116.6 (4)
O12i—Sm1—O893.53 (8)O9—C12—C13124.7 (4)
O11—Sm1—O877.97 (7)C17—C12—C13118.8 (4)
O4—Sm1—O8144.58 (8)C12—C13—C14121.0 (4)
O3—Sm1—O8142.00 (7)C12—C13—H13A119.5
O7i—Sm1—O773.80 (7)C14—C13—H13A119.5
O12i—Sm1—O771.45 (8)C15—C14—C13119.9 (4)
O11—Sm1—O771.33 (7)C15—C14—H14A120.1
O4—Sm1—O7148.95 (8)C13—C14—H14A120.1
O3—Sm1—O7140.55 (7)C14—C15—C16120.1 (4)
O8—Sm1—O750.76 (6)C14—C15—C19119.2 (3)
O7i—Sm1—N1142.48 (8)C16—C15—C19120.7 (4)
O12i—Sm1—N1138.87 (9)C15—C16—C17120.1 (4)
O11—Sm1—N179.86 (8)C15—C16—H16A120.0
O4—Sm1—N186.07 (9)C17—C16—H16A120.0
O3—Sm1—N171.45 (8)O10—C17—C12114.7 (4)
O8—Sm1—N176.46 (8)O10—C17—C16125.1 (4)
O7—Sm1—N1123.34 (8)C12—C17—C16120.1 (4)
O7i—Sm1—N2151.34 (8)O10—C18—H18A109.5
O12i—Sm1—N276.66 (8)O10—C18—H18B109.5
O11—Sm1—N2132.54 (8)H18A—C18—H18B109.5
O4—Sm1—N278.41 (8)O10—C18—H18C109.5
O3—Sm1—N2113.77 (8)H18A—C18—H18C109.5
O8—Sm1—N266.22 (7)H18B—C18—H18C109.5
O7—Sm1—N2104.89 (7)C20—C19—C15110.5 (3)
N1—Sm1—N262.70 (9)C20—C19—H19A109.5
O7i—Sm1—C1081.44 (8)C15—C19—H19A109.5
O12i—Sm1—C10102.32 (9)C20—C19—H19B109.5
O11—Sm1—C10102.99 (9)C15—C19—H19B109.5
O4—Sm1—C1026.38 (8)H19A—C19—H19B108.1
O3—Sm1—C1026.17 (8)O11—C20—O12126.1 (3)
O8—Sm1—C10153.37 (8)O11—C20—C19117.7 (3)
O7—Sm1—C10155.23 (8)O12—C20—C19116.1 (3)
N1—Sm1—C1077.54 (9)O5—C21—H21A109.5
N2—Sm1—C1096.56 (9)O5—C21—H21B109.5
O7i—Sm1—C3099.31 (8)H21A—C21—H21B109.5
O12i—Sm1—C3081.97 (8)O5—C21—H21C109.5
O11—Sm1—C3073.21 (8)H21A—C21—H21C109.5
O4—Sm1—C30157.47 (8)H21B—C21—H21C109.5
O3—Sm1—C30149.86 (8)C23—C22—O5125.4 (3)
O8—Sm1—C3024.81 (7)C23—C22—C27118.7 (3)
O7—Sm1—C3025.95 (7)O5—C22—C27116.0 (3)
N1—Sm1—C3099.58 (8)C22—C23—C24120.6 (3)
N2—Sm1—C3084.83 (8)C22—C23—H23A119.7
C10—Sm1—C30175.68 (8)C24—C23—H23A119.7
O7i—Sm1—Sm1i38.56 (5)C25—C24—C23121.6 (3)
O12i—Sm1—Sm1i69.33 (5)C25—C24—H24A119.2
O11—Sm1—Sm1i68.72 (5)C23—C24—H24A119.2
O4—Sm1—Sm1i122.84 (7)C24—C25—C26117.2 (3)
O3—Sm1—Sm1i110.82 (5)C24—C25—C29121.7 (3)
O8—Sm1—Sm1i85.51 (5)C26—C25—C29121.0 (3)
O7—Sm1—Sm1i35.24 (4)C27—C26—C25121.5 (3)
N1—Sm1—Sm1i146.45 (7)C27—C26—H26A119.3
N2—Sm1—Sm1i133.95 (6)C25—C26—H26A119.3
C10—Sm1—Sm1i119.99 (6)C26—C27—O6125.1 (3)
C30—Sm1—Sm1i60.89 (6)C26—C27—C22120.2 (3)
C31—N1—C42118.9 (3)O6—C27—C22114.6 (3)
C31—N1—Sm1120.7 (3)O6—C28—H28A109.5
C42—N1—Sm1119.8 (2)O6—C28—H28B109.5
C2—O1—C1116.7 (4)H28A—C28—H28B109.5
O1—C1—H1A109.5O6—C28—H28C109.5
O1—C1—H1B109.5H28A—C28—H28C109.5
H1A—C1—H1B109.5H28B—C28—H28C109.5
O1—C1—H1C109.5C25—C29—C30117.9 (3)
H1A—C1—H1C109.5C25—C29—H29A108.0
H1B—C1—H1C109.5C30—C29—H29A108.0
C40—N2—C41117.6 (3)C25—C29—H29B108.0
C40—N2—Sm1123.0 (2)C30—C29—H29B108.0
C41—N2—Sm1118.2 (2)H29A—C29—H29B107.0
C3—C2—O1126.0 (4)O8—C30—O7121.2 (3)
C3—C2—C7119.8 (3)O8—C30—C29122.8 (3)
O1—C2—C7114.2 (4)O7—C30—C29116.0 (3)
C7—O2—C8117.9 (3)O8—C30—Sm159.92 (16)
C10—O3—Sm191.70 (18)O7—C30—Sm161.30 (16)
C2—C3—C4120.5 (4)C29—C30—Sm1177.0 (2)
C2—C3—H3A119.8N1—C31—C32122.4 (4)
C4—C3—H3A119.8N1—C31—H31A118.8
C10—O4—Sm194.1 (2)C32—C31—H31A118.8
C5—C4—C3120.6 (4)C33—C32—C31119.1 (4)
C5—C4—H4A119.7C33—C32—H32A120.4
C3—C4—H4A119.7C31—C32—H32A120.4
C22—O5—C21116.1 (3)C32—C33—C34120.2 (4)
C6—C5—C4118.5 (3)C32—C33—H33A119.9
C6—C5—C9120.4 (4)C34—C33—H33A119.9
C4—C5—C9121.0 (4)C33—C34—C42117.5 (4)
C27—O6—C28116.8 (3)C33—C34—C35124.2 (4)
C7—C6—C5121.5 (4)C42—C34—C35118.3 (4)
C7—C6—H6A119.2C36—C35—C34122.8 (4)
C5—C6—H6A119.2C36—C35—H35A118.6
C30—O7—Sm1i158.2 (2)C34—C35—H35A118.6
C30—O7—Sm192.76 (18)C35—C36—C37119.8 (4)
Sm1i—O7—Sm1106.20 (7)C35—C36—H36A120.1
O2—C7—C6125.1 (4)C37—C36—H36A120.1
O2—C7—C2115.7 (3)C38—C37—C41117.7 (3)
C6—C7—C2119.1 (3)C38—C37—C36122.2 (4)
C30—O8—Sm195.27 (17)C41—C37—C36120.1 (4)
O2—C8—H8A109.5C39—C38—C37119.5 (3)
O2—C8—H8B109.5C39—C38—H38A120.3
H8A—C8—H8B109.5C37—C38—H38A120.3
O2—C8—H8C109.5C38—C39—C40119.2 (4)
H8A—C8—H8C109.5C38—C39—H39A120.4
H8B—C8—H8C109.5C40—C39—H39A120.4
C5—C9—C10114.8 (3)N2—C40—C39123.5 (4)
C5—C9—H9A108.6N2—C40—H40A118.3
C10—C9—H9A108.6C39—C40—H40A118.3
C5—C9—H9B108.6N2—C41—C37122.5 (3)
C10—C9—H9B108.6N2—C41—C42118.0 (3)
H9A—C9—H9B107.5C37—C41—C42119.5 (3)
C12—O9—C11116.9 (4)N1—C42—C34121.8 (4)
O3—C10—O4121.6 (3)N1—C42—C41118.9 (3)
O3—C10—C9120.9 (3)C34—C42—C41119.3 (3)
O4—C10—C9117.5 (3)C20—O12—Sm1i136.8 (2)
O3—C10—Sm162.13 (17)
O7i—Sm1—N1—C3114.7 (4)O7i—Sm1—C10—O4−104.6 (2)
O12i—Sm1—N1—C31166.7 (3)O12i—Sm1—C10—O4−31.1 (2)
O11—Sm1—N1—C31−33.7 (3)O11—Sm1—C10—O4−176.9 (2)
O4—Sm1—N1—C3197.4 (3)O3—Sm1—C10—O4179.9 (3)
O3—Sm1—N1—C3145.7 (3)O8—Sm1—C10—O494.0 (3)
O8—Sm1—N1—C31−113.7 (3)O7—Sm1—C10—O4−103.4 (3)
O7—Sm1—N1—C31−93.3 (3)N1—Sm1—C10—O4106.7 (2)
N2—Sm1—N1—C31176.4 (3)N2—Sm1—C10—O446.6 (2)
C10—Sm1—N1—C3172.1 (3)Sm1i—Sm1—C10—O4−104.2 (2)
C30—Sm1—N1—C31−104.6 (3)O7i—Sm1—O11—C2021.9 (3)
Sm1i—Sm1—N1—C31−54.2 (3)O12i—Sm1—O11—C20−26.2 (3)
O7i—Sm1—N1—C42−174.3 (2)O4—Sm1—O11—C2097.4 (3)
O12i—Sm1—N1—C42−22.3 (3)O3—Sm1—O11—C20100.6 (3)
O11—Sm1—N1—C42137.3 (2)O8—Sm1—O11—C20−108.1 (3)
O4—Sm1—N1—C42−91.6 (2)O7—Sm1—O11—C20−55.7 (3)
O3—Sm1—N1—C42−143.3 (2)N1—Sm1—O11—C20173.8 (3)
O8—Sm1—N1—C4257.4 (2)N2—Sm1—O11—C20−149.0 (3)
O7—Sm1—N1—C4277.8 (2)C10—Sm1—O11—C2099.2 (3)
N2—Sm1—N1—C42−12.6 (2)C30—Sm1—O11—C20−82.9 (3)
C10—Sm1—N1—C42−116.8 (2)Sm1i—Sm1—O11—C20−18.2 (3)
C30—Sm1—N1—C4266.5 (2)C11—O9—C12—C17177.4 (4)
Sm1i—Sm1—N1—C42116.8 (2)C11—O9—C12—C13−1.9 (7)
O7i—Sm1—N2—C40−23.7 (3)O9—C12—C13—C14179.7 (4)
O12i—Sm1—N2—C40−6.7 (3)C17—C12—C13—C140.5 (7)
O11—Sm1—N2—C40137.8 (2)C12—C13—C14—C150.0 (7)
O4—Sm1—N2—C40−88.6 (3)C13—C14—C15—C16−1.0 (6)
O3—Sm1—N2—C40−128.4 (3)C13—C14—C15—C19−179.7 (3)
O8—Sm1—N2—C4093.3 (3)C14—C15—C16—C171.5 (6)
O7—Sm1—N2—C4059.7 (3)C19—C15—C16—C17−179.8 (3)
N1—Sm1—N2—C40179.8 (3)C18—O10—C17—C12−172.9 (5)
C10—Sm1—N2—C40−107.8 (3)C18—O10—C17—C166.1 (7)
C30—Sm1—N2—C4076.3 (3)O9—C12—C17—O10−0.2 (6)
Sm1i—Sm1—N2—C4036.2 (3)C13—C12—C17—O10179.1 (4)
O7i—Sm1—N2—C41169.52 (19)O9—C12—C17—C16−179.3 (4)
O12i—Sm1—N2—C41−173.5 (2)C13—C12—C17—C160.0 (6)
O11—Sm1—N2—C41−29.0 (3)C15—C16—C17—O10180.0 (4)
O4—Sm1—N2—C41104.6 (2)C15—C16—C17—C12−1.0 (6)
O3—Sm1—N2—C4164.9 (2)C14—C15—C19—C20−49.5 (5)
O8—Sm1—N2—C41−73.5 (2)C16—C15—C19—C20131.7 (4)
O7—Sm1—N2—C41−107.1 (2)Sm1—O11—C20—O1225.7 (5)
N1—Sm1—N2—C4113.1 (2)Sm1—O11—C20—C19−152.8 (2)
C10—Sm1—N2—C4185.4 (2)C15—C19—C20—O11105.0 (4)
C30—Sm1—N2—C41−90.5 (2)C15—C19—C20—O12−73.7 (4)
Sm1i—Sm1—N2—C41−130.55 (19)C21—O5—C22—C2317.6 (5)
C1—O1—C2—C33.9 (6)C21—O5—C22—C27−162.3 (3)
C1—O1—C2—C7−175.5 (4)O5—C22—C23—C24−177.4 (3)
O7i—Sm1—O3—C10−99.26 (19)C27—C22—C23—C242.6 (5)
O12i—Sm1—O3—C10−37.5 (2)C22—C23—C24—C251.6 (6)
O11—Sm1—O3—C10−176.9 (2)C23—C24—C25—C26−5.1 (6)
O4—Sm1—O3—C100.05 (18)C23—C24—C25—C29172.1 (4)
O8—Sm1—O3—C10133.44 (19)C24—C25—C26—C274.5 (5)
O7—Sm1—O3—C10−140.09 (18)C29—C25—C26—C27−172.8 (3)
N1—Sm1—O3—C1099.6 (2)C25—C26—C27—O6179.1 (3)
N2—Sm1—O3—C1052.2 (2)C25—C26—C27—C22−0.4 (5)
C30—Sm1—O3—C10176.40 (16)C28—O6—C27—C2615.4 (6)
Sm1i—Sm1—O3—C10−116.03 (18)C28—O6—C27—C22−165.0 (4)
O1—C2—C3—C4−177.7 (4)C23—C22—C27—C26−3.2 (5)
C7—C2—C3—C41.7 (6)O5—C22—C27—C26176.8 (3)
O7i—Sm1—O4—C1073.2 (2)C23—C22—C27—O6177.2 (3)
O12i—Sm1—O4—C10149.1 (2)O5—C22—C27—O6−2.8 (4)
O11—Sm1—O4—C103.9 (2)C24—C25—C29—C30125.6 (4)
O3—Sm1—O4—C10−0.05 (18)C26—C25—C29—C30−57.3 (5)
O8—Sm1—O4—C10−129.52 (19)Sm1—O8—C30—O7−0.6 (3)
O7—Sm1—O4—C10127.8 (2)Sm1—O8—C30—C29178.4 (3)
N1—Sm1—O4—C10−69.6 (2)Sm1i—O7—C30—O8−150.3 (4)
N2—Sm1—O4—C10−132.5 (2)Sm1—O7—C30—O80.6 (3)
C30—Sm1—O4—C10−175.27 (18)Sm1i—O7—C30—C2930.7 (7)
Sm1i—Sm1—O4—C1092.2 (2)Sm1—O7—C30—C29−178.5 (3)
C2—C3—C4—C5−0.8 (6)Sm1i—O7—C30—Sm1−150.8 (5)
C3—C4—C5—C6−0.8 (6)C25—C29—C30—O8−6.2 (5)
C3—C4—C5—C9−179.2 (4)C25—C29—C30—O7172.8 (3)
C4—C5—C6—C71.5 (5)O7i—Sm1—C30—O8−168.86 (18)
C9—C5—C6—C7179.9 (3)O12i—Sm1—C30—O8116.95 (19)
O7i—Sm1—O7—C30−169.2 (2)O11—Sm1—C30—O8−97.69 (19)
O12i—Sm1—O7—C30110.65 (18)O4—Sm1—C30—O881.6 (3)
O11—Sm1—O7—C30−89.85 (18)O3—Sm1—C30—O8−90.8 (2)
O4—Sm1—O7—C30132.80 (19)O7—Sm1—C30—O8−179.4 (3)
O3—Sm1—O7—C30−127.81 (17)N1—Sm1—C30—O8−21.4 (2)
O8—Sm1—O7—C30−0.31 (16)N2—Sm1—C30—O839.73 (19)
N1—Sm1—O7—C30−26.3 (2)Sm1i—Sm1—C30—O8−172.3 (2)
N2—Sm1—O7—C3040.59 (18)O7i—Sm1—C30—O710.6 (2)
C10—Sm1—O7—C30−170.29 (18)O12i—Sm1—C30—O7−63.63 (17)
Sm1i—Sm1—O7—C30−169.2 (2)O11—Sm1—C30—O781.73 (17)
O7i—Sm1—O7—Sm1i0.0O4—Sm1—C30—O7−99.0 (3)
O12i—Sm1—O7—Sm1i−80.20 (9)O3—Sm1—C30—O788.6 (2)
O11—Sm1—O7—Sm1i79.30 (9)O8—Sm1—C30—O7179.4 (3)
O4—Sm1—O7—Sm1i−58.05 (17)N1—Sm1—C30—O7157.99 (17)
O3—Sm1—O7—Sm1i41.34 (14)N2—Sm1—C30—O7−140.85 (17)
O8—Sm1—O7—Sm1i168.84 (13)Sm1i—Sm1—C30—O77.14 (14)
N1—Sm1—O7—Sm1i142.90 (9)C42—N1—C31—C32−1.0 (6)
N2—Sm1—O7—Sm1i−150.26 (9)Sm1—N1—C31—C32170.1 (3)
C10—Sm1—O7—Sm1i−1.1 (2)N1—C31—C32—C33−1.5 (6)
C30—Sm1—O7—Sm1i169.2 (2)C31—C32—C33—C341.5 (6)
C8—O2—C7—C69.9 (6)C32—C33—C34—C420.8 (6)
C8—O2—C7—C2−172.0 (4)C32—C33—C34—C35−179.0 (4)
C5—C6—C7—O2177.4 (3)C33—C34—C35—C36−177.7 (4)
C5—C6—C7—C2−0.7 (5)C42—C34—C35—C362.5 (6)
C3—C2—C7—O2−179.2 (4)C34—C35—C36—C370.9 (6)
O1—C2—C7—O20.2 (5)C35—C36—C37—C38176.8 (4)
C3—C2—C7—C6−0.9 (6)C35—C36—C37—C41−3.8 (6)
O1—C2—C7—C6178.5 (3)C41—C37—C38—C39−2.6 (5)
O7i—Sm1—O8—C3013.2 (2)C36—C37—C38—C39176.9 (3)
O12i—Sm1—O8—C30−62.17 (19)C37—C38—C39—C401.0 (6)
O11—Sm1—O8—C3075.94 (19)C41—N2—C40—C39−1.5 (5)
O4—Sm1—O8—C30−139.16 (19)Sm1—N2—C40—C39−168.4 (3)
O3—Sm1—O8—C30125.36 (19)C38—C39—C40—N21.2 (6)
O7—Sm1—O8—C300.33 (17)C40—N2—C41—C37−0.3 (5)
N1—Sm1—O8—C30158.3 (2)Sm1—N2—C41—C37167.2 (2)
N2—Sm1—O8—C30−135.9 (2)C40—N2—C41—C42179.5 (3)
C10—Sm1—O8—C30170.97 (18)Sm1—N2—C41—C42−13.0 (4)
Sm1i—Sm1—O8—C306.76 (18)C38—C37—C41—N22.3 (5)
C6—C5—C9—C10−105.2 (4)C36—C37—C41—N2−177.2 (3)
C4—C5—C9—C1073.1 (5)C38—C37—C41—C42−177.4 (3)
Sm1—O3—C10—O4−0.1 (3)C36—C37—C41—C423.1 (5)
Sm1—O3—C10—C9−179.7 (3)C31—N1—C42—C343.5 (5)
Sm1—O4—C10—O30.1 (3)Sm1—N1—C42—C34−167.7 (2)
Sm1—O4—C10—C9179.7 (3)C31—N1—C42—C41−176.9 (3)
C5—C9—C10—O3−10.5 (5)Sm1—N1—C42—C4111.9 (4)
C5—C9—C10—O4169.9 (3)C33—C34—C42—N1−3.4 (5)
O7i—Sm1—C10—O375.53 (19)C35—C34—C42—N1176.4 (3)
O12i—Sm1—C10—O3148.96 (18)C33—C34—C42—C41177.1 (3)
O11—Sm1—C10—O33.1 (2)C35—C34—C42—C41−3.1 (5)
O4—Sm1—C10—O3−179.9 (3)N2—C41—C42—N11.1 (4)
O8—Sm1—C10—O3−85.9 (3)C37—C41—C42—N1−179.1 (3)
O7—Sm1—C10—O376.6 (3)N2—C41—C42—C34−179.4 (3)
N1—Sm1—C10—O3−73.20 (19)C37—C41—C42—C340.4 (5)
N2—Sm1—C10—O3−133.32 (19)O11—C20—O12—Sm1i−12.2 (6)
Sm1i—Sm1—C10—O375.88 (19)C19—C20—O12—Sm1i166.3 (2)

Symmetry codes: (i) −x, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C1—H1A···O5ii0.962.543.323 (5)139
C21—H21C···O4iii0.962.363.274 (5)160
C23—H23A···O4iii0.932.523.404 (4)160
C31—H31A···O30.932.553.040 (5)113

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2022).

References

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