Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003076/cf6236sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003076/cf6236Isup2.hkl |
CCDC reference: 206735
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.008 Å
- R factor = 0.043
- wR factor = 0.105
- Data-to-parameter ratio = 17.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
FORMU_01 There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C50 H61 Cl2 N4 O1 Sm1 Atom count from _chemical_formula_moiety:
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT and SHELXTL (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Sm(C24H25)(C4H6N2)2(C4H8O)Cl2]·2C7H8 | F(000) = 1972 |
Mr = 955.28 | Dx = 1.341 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 7462 reflections |
a = 21.5031 (2) Å | θ = 2.1–28.2° |
b = 13.9259 (2) Å | µ = 1.39 mm−1 |
c = 17.6668 (2) Å | T = 173 K |
β = 116.5360 (4)° | Block, yellow |
V = 4733.01 (10) Å3 | 0.50 × 0.40 × 0.20 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 4686 independent reflections |
Radiation source: fine-focus sealed tube | 4054 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 26.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −26→23 |
Tmin = 0.543, Tmax = 0.768 | k = −15→17 |
10236 measured reflections | l = −22→18 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.21 | w = 1/[σ2(Fo2) + (0.0301P)2 + 28.1537P] where P = (Fo2 + 2Fc2)/3 |
4686 reflections | (Δ/σ)max = 0.005 |
267 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.56 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 | 0.5000 | 0.00112 (2) | 0.7500 | 0.02381 (10) | |
Cl1 | 0.42150 (6) | 0.02205 (8) | 0.58340 (7) | 0.0366 (3) | |
O1 | 0.5000 | 0.1879 (3) | 0.7500 | 0.0415 (12) | |
N1 | 0.4023 (2) | 0.0618 (2) | 0.7775 (2) | 0.0296 (8) | |
N2 | 0.3473 (2) | 0.1300 (3) | 0.8428 (2) | 0.0355 (9) | |
C1 | 0.5000 | −0.1807 (4) | 0.7500 | 0.0218 (11) | |
C2 | 0.4472 (2) | −0.2356 (3) | 0.7569 (2) | 0.0236 (8) | |
C3 | 0.4467 (3) | −0.3361 (3) | 0.7558 (3) | 0.0328 (10) | |
H3A | 0.4097 | −0.3701 | 0.7591 | 0.039* | |
C4 | 0.5000 | −0.3860 (4) | 0.7500 | 0.0381 (16) | |
H4A | 0.5000 | −0.4542 | 0.7500 | 0.046* | |
C5 | 0.3268 (2) | −0.1626 (3) | 0.6954 (3) | 0.0289 (9) | |
C6 | 0.2729 (2) | −0.1211 (3) | 0.7072 (3) | 0.0330 (10) | |
H6A | 0.2313 | −0.1037 | 0.6591 | 0.040* | |
C7 | 0.2781 (3) | −0.1043 (3) | 0.7876 (3) | 0.0360 (10) | |
C8 | 0.3388 (3) | −0.1306 (3) | 0.8572 (3) | 0.0349 (10) | |
H8A | 0.3426 | −0.1207 | 0.9123 | 0.042* | |
C9 | 0.3945 (2) | −0.1710 (3) | 0.8487 (3) | 0.0280 (9) | |
C10 | 0.3885 (2) | −0.1878 (3) | 0.7670 (2) | 0.0245 (8) | |
C11 | 0.3181 (2) | −0.1813 (4) | 0.6068 (3) | 0.0377 (11) | |
H11A | 0.2751 | −0.1510 | 0.5656 | 0.057* | |
H11B | 0.3158 | −0.2507 | 0.5965 | 0.057* | |
H11C | 0.3578 | −0.1543 | 0.6008 | 0.057* | |
C12 | 0.2184 (3) | −0.0596 (5) | 0.7987 (4) | 0.0575 (15) | |
H12A | 0.2320 | −0.0506 | 0.8591 | 0.086* | |
H12B | 0.1778 | −0.1020 | 0.7741 | 0.086* | |
H12C | 0.2067 | 0.0028 | 0.7699 | 0.086* | |
C13 | 0.4611 (3) | −0.1948 (4) | 0.9268 (3) | 0.0382 (11) | |
H13A | 0.4558 | −0.1787 | 0.9776 | 0.057* | |
H13B | 0.4995 | −0.1575 | 0.9262 | 0.057* | |
H13C | 0.4711 | −0.2635 | 0.9270 | 0.057* | |
C14 | 0.4011 (2) | 0.0756 (3) | 0.8510 (3) | 0.0327 (10) | |
H14A | 0.4344 | 0.0498 | 0.9032 | 0.039* | |
C15 | 0.3107 (3) | 0.1532 (4) | 0.7585 (3) | 0.0408 (11) | |
H15A | 0.2701 | 0.1917 | 0.7333 | 0.049* | |
C16 | 0.3442 (3) | 0.1101 (4) | 0.7190 (3) | 0.0398 (11) | |
H16A | 0.3302 | 0.1124 | 0.6598 | 0.048* | |
C17 | 0.3300 (3) | 0.1593 (4) | 0.9111 (3) | 0.0498 (13) | |
H17A | 0.3646 | 0.1330 | 0.9650 | 0.075* | |
H17B | 0.2838 | 0.1349 | 0.8993 | 0.075* | |
H17C | 0.3301 | 0.2295 | 0.9146 | 0.075* | |
C18 | 0.4905 (4) | 0.2485 (4) | 0.6794 (4) | 0.0607 (17) | |
H18A | 0.5291 | 0.2391 | 0.6641 | 0.073* | |
H18B | 0.4462 | 0.2325 | 0.6296 | 0.073* | |
C19 | 0.4891 (5) | 0.3474 (4) | 0.7051 (4) | 0.093 (3) | |
H19A | 0.4416 | 0.3741 | 0.6747 | 0.111* | |
H19B | 0.5210 | 0.3873 | 0.6917 | 0.111* | |
C20 | 0.1582 (4) | 0.0697 (6) | 0.5155 (5) | 0.081 (2) | |
C21 | 0.1296 (3) | 0.0760 (5) | 0.5734 (4) | 0.0617 (18) | |
H21A | 0.1373 | 0.1322 | 0.6069 | 0.074* | |
C22 | 0.0909 (4) | 0.0026 (6) | 0.5821 (5) | 0.084 (3) | |
H22A | 0.0728 | 0.0088 | 0.6221 | 0.101* | |
C23 | 0.0781 (4) | −0.0763 (6) | 0.5366 (4) | 0.077 (2) | |
H23A | 0.0513 | −0.1266 | 0.5437 | 0.092* | |
C24 | 0.1045 (3) | −0.0850 (5) | 0.4777 (4) | 0.0600 (17) | |
H24A | 0.0943 | −0.1418 | 0.4446 | 0.072* | |
C25 | 0.1443 (4) | −0.0162 (5) | 0.4651 (4) | 0.0658 (18) | |
H25A | 0.1620 | −0.0247 | 0.4250 | 0.079* | |
C26 | 0.2002 (6) | 0.1452 (7) | 0.5039 (6) | 0.118 (4) | |
H26A | 0.2049 | 0.1988 | 0.5419 | 0.177* | |
H26B | 0.1776 | 0.1676 | 0.4451 | 0.177* | |
H26C | 0.2463 | 0.1197 | 0.5167 | 0.177* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sm1 | 0.03036 (17) | 0.01505 (14) | 0.02346 (15) | 0.000 | 0.00974 (11) | 0.000 |
Cl1 | 0.0414 (6) | 0.0337 (6) | 0.0254 (5) | −0.0050 (4) | 0.0065 (4) | 0.0015 (4) |
O1 | 0.057 (3) | 0.020 (2) | 0.055 (3) | 0.000 | 0.032 (3) | 0.000 |
N1 | 0.032 (2) | 0.0223 (18) | 0.0344 (19) | −0.0004 (14) | 0.0147 (16) | 0.0003 (14) |
N2 | 0.038 (2) | 0.030 (2) | 0.039 (2) | 0.0062 (17) | 0.0173 (18) | 0.0014 (16) |
C1 | 0.025 (3) | 0.018 (3) | 0.022 (3) | 0.000 | 0.011 (2) | 0.000 |
C2 | 0.025 (2) | 0.0204 (19) | 0.0228 (19) | −0.0026 (15) | 0.0088 (16) | 0.0000 (15) |
C3 | 0.042 (3) | 0.021 (2) | 0.036 (2) | −0.0063 (18) | 0.018 (2) | −0.0005 (17) |
C4 | 0.054 (4) | 0.018 (3) | 0.046 (4) | 0.000 | 0.026 (3) | 0.000 |
C5 | 0.029 (2) | 0.028 (2) | 0.030 (2) | −0.0089 (17) | 0.0132 (18) | −0.0005 (17) |
C6 | 0.022 (2) | 0.033 (2) | 0.040 (2) | −0.0019 (18) | 0.0108 (19) | 0.0033 (19) |
C7 | 0.034 (3) | 0.031 (2) | 0.051 (3) | −0.0022 (19) | 0.025 (2) | 0.000 (2) |
C8 | 0.045 (3) | 0.035 (2) | 0.031 (2) | −0.008 (2) | 0.023 (2) | −0.0023 (19) |
C9 | 0.031 (2) | 0.023 (2) | 0.029 (2) | −0.0036 (17) | 0.0135 (18) | 0.0001 (16) |
C10 | 0.029 (2) | 0.0176 (18) | 0.026 (2) | −0.0048 (15) | 0.0116 (17) | −0.0006 (15) |
C11 | 0.031 (3) | 0.049 (3) | 0.028 (2) | −0.007 (2) | 0.0084 (19) | 0.001 (2) |
C12 | 0.051 (4) | 0.067 (4) | 0.068 (4) | 0.010 (3) | 0.039 (3) | 0.001 (3) |
C13 | 0.041 (3) | 0.045 (3) | 0.025 (2) | 0.000 (2) | 0.012 (2) | 0.0029 (19) |
C14 | 0.031 (2) | 0.024 (2) | 0.040 (2) | 0.0022 (18) | 0.013 (2) | 0.0028 (18) |
C15 | 0.032 (3) | 0.047 (3) | 0.039 (3) | 0.008 (2) | 0.012 (2) | 0.003 (2) |
C16 | 0.040 (3) | 0.040 (3) | 0.034 (2) | 0.009 (2) | 0.011 (2) | 0.005 (2) |
C17 | 0.056 (4) | 0.051 (3) | 0.048 (3) | 0.014 (3) | 0.029 (3) | 0.001 (2) |
C18 | 0.099 (5) | 0.027 (3) | 0.059 (4) | 0.007 (3) | 0.037 (4) | 0.009 (2) |
C19 | 0.164 (9) | 0.026 (3) | 0.073 (4) | 0.004 (4) | 0.039 (5) | 0.005 (3) |
C20 | 0.058 (4) | 0.063 (4) | 0.076 (5) | 0.009 (3) | −0.010 (4) | 0.010 (4) |
C21 | 0.044 (4) | 0.067 (4) | 0.053 (4) | 0.013 (3) | 0.004 (3) | −0.025 (3) |
C22 | 0.041 (4) | 0.101 (6) | 0.086 (5) | 0.009 (4) | 0.007 (3) | −0.034 (5) |
C23 | 0.054 (4) | 0.096 (6) | 0.062 (4) | 0.024 (4) | 0.010 (3) | −0.016 (4) |
C24 | 0.058 (4) | 0.065 (4) | 0.045 (3) | 0.022 (3) | 0.012 (3) | −0.002 (3) |
C25 | 0.069 (4) | 0.058 (4) | 0.054 (4) | 0.011 (3) | 0.013 (3) | 0.001 (3) |
C26 | 0.124 (8) | 0.094 (7) | 0.088 (6) | −0.009 (6) | 0.004 (6) | 0.022 (5) |
Sm1—N1i | 2.505 (4) | C12—H12A | 0.980 |
Sm1—N1 | 2.505 (4) | C12—H12B | 0.980 |
Sm1—C1 | 2.532 (5) | C12—H12C | 0.980 |
Sm1—O1 | 2.601 (4) | C13—H13A | 0.980 |
Sm1—Cl1 | 2.6754 (10) | C13—H13B | 0.980 |
Sm1—Cl1i | 2.6754 (10) | C13—H13C | 0.980 |
O1—C18 | 1.442 (6) | C14—H14A | 0.950 |
O1—C18i | 1.442 (6) | C15—C16 | 1.348 (7) |
N1—C14 | 1.324 (6) | C15—H15A | 0.950 |
N1—C16 | 1.388 (6) | C16—H16A | 0.950 |
N2—C14 | 1.335 (6) | C17—H17A | 0.980 |
N2—C15 | 1.377 (6) | C17—H17B | 0.980 |
N2—C17 | 1.470 (6) | C17—H17C | 0.980 |
C1—C2i | 1.418 (5) | C18—C19 | 1.455 (8) |
C1—C2 | 1.418 (5) | C18—H18A | 0.990 |
C2—C3 | 1.400 (6) | C18—H18B | 0.990 |
C2—C10 | 1.507 (6) | C19—C19i | 1.440 (14) |
C3—C4 | 1.383 (6) | C19—H19A | 0.990 |
C3—H3A | 0.950 | C19—H19B | 0.990 |
C4—C3i | 1.383 (6) | C20—C25 | 1.441 (10) |
C4—H4A | 0.950 | C20—C21 | 1.411 (11) |
C5—C6 | 1.392 (6) | C20—C26 | 1.459 (12) |
C5—C10 | 1.409 (6) | C21—C22 | 1.369 (11) |
C5—C11 | 1.514 (6) | C21—H21A | 0.950 |
C6—C7 | 1.394 (7) | C22—C23 | 1.316 (10) |
C6—H6A | 0.950 | C22—H22A | 0.950 |
C7—C8 | 1.384 (7) | C23—C24 | 1.395 (10) |
C7—C12 | 1.515 (7) | C23—H23A | 0.950 |
C8—C9 | 1.390 (7) | C24—C25 | 1.367 (10) |
C8—H8A | 0.950 | C24—H24A | 0.950 |
C9—C10 | 1.410 (6) | C25—H25A | 0.950 |
C9—C13 | 1.516 (6) | C26—H26A | 0.980 |
C11—H11A | 0.980 | C26—H26B | 0.980 |
C11—H11B | 0.980 | C26—H26C | 0.980 |
C11—H11C | 0.980 | ||
N1i—Sm1—N1 | 140.56 (16) | H12A—C12—H12B | 109.5 |
N1i—Sm1—C1 | 109.72 (8) | C7—C12—H12C | 109.5 |
N1—Sm1—C1 | 109.72 (8) | H12A—C12—H12C | 109.5 |
N1i—Sm1—O1 | 70.28 (8) | H12B—C12—H12C | 109.5 |
N1—Sm1—O1 | 70.28 (8) | C9—C13—H13A | 109.5 |
C1—Sm1—O1 | 180 | C9—C13—H13B | 109.5 |
N1i—Sm1—Cl1 | 85.48 (9) | H13A—C13—H13B | 109.5 |
N1—Sm1—Cl1 | 90.30 (9) | C9—C13—H13C | 109.5 |
C1—Sm1—Cl1 | 96.25 (2) | H13A—C13—H13C | 109.5 |
O1—Sm1—Cl1 | 83.75 (2) | H13B—C13—H13C | 109.5 |
N1i—Sm1—Cl1i | 90.30 (9) | N1—C14—N2 | 111.8 (4) |
N1—Sm1—Cl1i | 85.48 (9) | N1—C14—H14A | 124.1 |
C1—Sm1—Cl1i | 96.25 (2) | N2—C14—H14A | 124.1 |
O1—Sm1—Cl1i | 83.75 (2) | C16—C15—N2 | 106.1 (4) |
Cl1—Sm1—Cl1i | 167.50 (5) | C16—C15—H15A | 127.0 |
C18—O1—C18i | 108.5 (5) | N2—C15—H15A | 127.0 |
C18—O1—Sm1 | 125.8 (3) | C15—C16—N1 | 109.9 (4) |
C18i—O1—Sm1 | 125.8 (3) | C15—C16—H16A | 125.0 |
C14—N1—C16 | 104.8 (4) | N1—C16—H16A | 125.0 |
C14—N1—Sm1 | 128.7 (3) | N2—C17—H17A | 109.5 |
C16—N1—Sm1 | 124.8 (3) | N2—C17—H17B | 109.5 |
C14—N2—C15 | 107.4 (4) | H17A—C17—H17B | 109.5 |
C14—N2—C17 | 126.4 (4) | N2—C17—H17C | 109.5 |
C15—N2—C17 | 126.2 (4) | H17A—C17—H17C | 109.5 |
C2i—C1—C2 | 114.7 (5) | H17B—C17—H17C | 109.5 |
C2i—C1—Sm1 | 122.6 (2) | C19—C18—O1 | 107.4 (5) |
C2—C1—Sm1 | 122.6 (2) | C19—C18—H18A | 110.2 |
C3—C2—C1 | 122.7 (4) | O1—C18—H18A | 110.2 |
C3—C2—C10 | 116.1 (4) | C19—C18—H18B | 110.2 |
C1—C2—C10 | 121.1 (4) | O1—C18—H18B | 110.2 |
C2—C3—C4 | 120.0 (4) | H18A—C18—H18B | 108.5 |
C2—C3—H3A | 120.0 | C18—C19—C19i | 107.6 (4) |
C4—C3—H3A | 120.0 | C18—C19—H19A | 110.2 |
C3i—C4—C3 | 119.7 (6) | C19i—C19—H19A | 110.2 |
C3i—C4—H4A | 120.1 | C18—C19—H19B | 110.2 |
C3—C4—H4A | 120.1 | C19i—C19—H19B | 110.2 |
C6—C5—C10 | 118.8 (4) | H19A—C19—H19B | 108.5 |
C6—C5—C11 | 120.0 (4) | C25—C20—C21 | 117.5 (7) |
C10—C5—C11 | 121.2 (4) | C25—C20—C26 | 118.8 (9) |
C5—C6—C7 | 122.0 (4) | C21—C20—C26 | 123.7 (8) |
C5—C6—H6A | 119.0 | C22—C21—C20 | 121.2 (7) |
C7—C6—H6A | 119.0 | C22—C21—H21A | 119.4 |
C8—C7—C6 | 118.3 (4) | C20—C21—H21A | 119.4 |
C8—C7—C12 | 120.8 (5) | C23—C22—C21 | 121.7 (9) |
C6—C7—C12 | 120.9 (5) | C23—C22—H22A | 119.1 |
C7—C8—C9 | 121.9 (4) | C21—C22—H22A | 119.1 |
C7—C8—H8A | 119.1 | C22—C23—C24 | 118.9 (9) |
C9—C8—H8A | 119.1 | C22—C23—H23A | 120.5 |
C8—C9—C10 | 119.2 (4) | C24—C23—H23A | 120.5 |
C8—C9—C13 | 120.0 (4) | C25—C24—C23 | 123.6 (7) |
C10—C9—C13 | 120.8 (4) | C25—C24—H24A | 118.2 |
C5—C10—C9 | 119.8 (4) | C23—C24—H24A | 118.2 |
C5—C10—C2 | 120.4 (4) | C24—C25—C20 | 116.9 (7) |
C9—C10—C2 | 119.8 (4) | C24—C25—H25A | 121.5 |
C5—C11—H11A | 109.5 | C20—C25—H25A | 121.5 |
C5—C11—H11B | 109.5 | C20—C26—H26A | 109.5 |
H11A—C11—H11B | 109.5 | C20—C26—H26B | 109.5 |
C5—C11—H11C | 109.5 | H26A—C26—H26B | 109.5 |
H11A—C11—H11C | 109.5 | C20—C26—H26C | 109.5 |
H11B—C11—H11C | 109.5 | H26A—C26—H26C | 109.5 |
C7—C12—H12A | 109.5 | H26B—C26—H26C | 109.5 |
C7—C12—H12B | 109.5 |
Symmetry code: (i) −x+1, y, −z+3/2. |
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