In the title compound, [Sm(NO3)3(C24H28N4O2)], the Sm atom has tenfold coordination, built up from two imino N atoms, two deprotonated phenolic O atoms and three bidentate nitrate groups. The Sm ion is incorporated in an out-of-plane position relative to the macrocyclic ligand, which adopts a folded conformation.
Supporting information
CCDC reference: 298451
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.012 Å
- R factor = 0.070
- wR factor = 0.079
- Data-to-parameter ratio = 10.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT021_ALERT_1_B Ratio Unique / Expected Reflections too High ... 1.05
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.94
Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
PLAT213_ALERT_2_C Atom O8 has ADP max/min Ratio ............. 3.40 prolat
PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.93 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Sm1 - O4 .. 6.11 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O7
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Sm1
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N6
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 12
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
12 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 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
Data collection: KappaCCD Software (Nonius, 1997); cell refinement: KappaCCD Software; data reduction: TEXSAN (Molecular Structure Corporation, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: TEXSAN; molecular graphics: Please supply; software used to prepare material for publication: TEXSAN.
[11,23-Dimethyl-15,19-diaza-3,7-diazoniatricyclo[19.3.1.1
9,13]trtracosa-
1(25),2,7,9,11,13 (26),14,19,21,23-decaene-25,26-doiolato-
κ4N15,
N19,
O,
O']tris(nitrato-
κ2O,
O')samarium(III)
top
Crystal data top
[Sm(NO3)3(C24H28N4O2)] | F(000) = 1484.00 |
Mr = 740.93 | Dx = 1.734 Mg m−3 |
Monoclinic, P21/c | Ag Kα radiation, λ = 0.5608 Å |
Hall symbol: -P 2ybc | Cell parameters from 987 reflections |
a = 15.7532 (13) Å | θ = 3.0–17.0° |
b = 9.7237 (5) Å | µ = 1.15 mm−1 |
c = 19.1342 (15) Å | T = 293 K |
β = 104.457 (12)° | Prism, colorless |
V = 2838.1 (4) Å3 | 0.20 × 0.15 × 0.10 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD diffractometer | 4029 reflections with I > 2σ(I) |
Radiation source: X-ray tube | Rint = 0.082 |
Filter monochromator | θmax = 20.5°, θmin = 2.2° |
ω and φ scans | h = −19→19 |
30402 measured reflections | k = −12→12 |
6093 independent reflections | l = −23→23 |
Refinement top
Refinement on F | 0 restraints |
Least-squares matrix: full | 0 constraints |
R[F2 > 2σ(F2)] = 0.070 | H-atom parameters constrained |
wR(F2) = 0.079 | Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00006|Fo|2] |
S = 1.61 | (Δ/σ)max = 0.005 |
4029 reflections | Δρmax = 1.71 e Å−3 |
388 parameters | Δρmin = −1.71 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Sm1 | 0.26164 (3) | 0.15966 (4) | 0.58249 (2) | 0.0343 (1) | |
O1 | 0.3570 (3) | 0.3467 (5) | 0.5931 (3) | 0.043 (2) | |
O2 | 0.1766 (4) | 0.3576 (5) | 0.5472 (3) | 0.039 (1) | |
O3 | 0.4194 (4) | 0.0995 (6) | 0.6609 (4) | 0.059 (2) | |
O4 | 0.3480 (4) | −0.0724 (6) | 0.6078 (4) | 0.055 (2) | |
O5 | 0.4814 (5) | −0.0991 (8) | 0.6697 (5) | 0.087 (3) | |
O6 | 0.1672 (4) | −0.0562 (6) | 0.5787 (4) | 0.057 (2) | |
O7 | 0.1033 (4) | 0.1277 (6) | 0.5981 (4) | 0.064 (2) | |
O8 | 0.0419 (4) | −0.0665 (7) | 0.6027 (6) | 0.115 (3) | |
O9 | 0.2589 (5) | 0.0869 (7) | 0.7149 (4) | 0.066 (2) | |
O10 | 0.2386 (5) | 0.2312 (9) | 0.7957 (4) | 0.090 (3) | |
O11 | 0.2512 (4) | 0.3023 (6) | 0.6920 (3) | 0.051 (2) | |
N1 | 0.1632 (4) | 0.5723 (7) | 0.6271 (4) | 0.046 (2) | |
N2 | 0.1699 (4) | 0.1311 (6) | 0.4502 (4) | 0.041 (2) | |
N3 | 0.3611 (4) | 0.1298 (7) | 0.4915 (4) | 0.044 (2) | |
N4 | 0.3764 (4) | 0.5437 (7) | 0.6926 (4) | 0.046 (2) | |
N5 | 0.4179 (5) | −0.0252 (7) | 0.6467 (4) | 0.050 (2) | |
N6 | 0.1021 (5) | −0.0010 (7) | 0.5937 (5) | 0.062 (2) | |
N7 | 0.2492 (5) | 0.2062 (8) | 0.7361 (5) | 0.054 (2) | |
C1 | 0.2634 (7) | −0.064 (1) | 0.4337 (6) | 0.079 (3) | |
C2 | 0.1742 (6) | −0.0068 (9) | 0.4185 (5) | 0.056 (3) | |
C3 | 0.1266 (5) | 0.2210 (9) | 0.4071 (5) | 0.044 (2) | |
C4 | 0.1076 (5) | 0.3632 (8) | 0.4217 (4) | 0.036 (2) | |
C5 | 0.0647 (5) | 0.4434 (9) | 0.3636 (5) | 0.049 (3) | |
C6 | 0.0404 (5) | 0.5780 (9) | 0.3700 (5) | 0.048 (3) | |
C7 | −0.0055 (7) | 0.661 (1) | 0.3033 (6) | 0.071 (3) | |
C8 | 0.0574 (6) | 0.6351 (8) | 0.4384 (5) | 0.050 (3) | |
C9 | 0.1042 (4) | 0.5621 (7) | 0.4999 (4) | 0.033 (2) | |
C10 | 0.1319 (4) | 0.4212 (7) | 0.4914 (4) | 0.032 (2) | |
C11 | 0.1199 (5) | 0.6280 (8) | 0.5670 (5) | 0.043 (2) | |
C12 | 0.1800 (6) | 0.6407 (9) | 0.6978 (5) | 0.054 (3) | |
C13 | 0.2693 (6) | 0.7121 (9) | 0.7218 (5) | 0.059 (3) | |
C14 | 0.3464 (6) | 0.6189 (9) | 0.7474 (5) | 0.056 (3) | |
C15 | 0.4529 (5) | 0.5578 (9) | 0.6811 (5) | 0.046 (3) | |
C16 | 0.4866 (5) | 0.4780 (9) | 0.6314 (5) | 0.043 (2) | |
C17 | 0.5719 (5) | 0.5065 (9) | 0.6268 (5) | 0.053 (3) | |
C18 | 0.6095 (5) | 0.4362 (9) | 0.5806 (6) | 0.055 (3) | |
C19 | 0.7038 (6) | 0.467 (1) | 0.5742 (7) | 0.078 (4) | |
C20 | 0.5620 (5) | 0.3351 (9) | 0.5385 (5) | 0.053 (3) | |
C21 | 0.4758 (5) | 0.2989 (8) | 0.5414 (5) | 0.045 (2) | |
C22 | 0.4361 (5) | 0.3717 (8) | 0.5883 (5) | 0.041 (2) | |
C23 | 0.4325 (6) | 0.1905 (9) | 0.4936 (5) | 0.051 (3) | |
C24 | 0.3369 (7) | 0.026 (1) | 0.4334 (6) | 0.071 (3) | |
H1 | 0.2747 | −0.1045 | 0.4802 | 0.094* | |
H2 | 0.2629 | −0.1333 | 0.3986 | 0.094* | |
H3 | 0.1385 | −0.0677 | 0.4375 | 0.068* | |
H4 | 0.1521 | −0.0003 | 0.3676 | 0.068* | |
H5 | 0.1035 | 0.1910 | 0.3588 | 0.053* | |
H6 | 0.0514 | 0.4033 | 0.3169 | 0.059* | |
H7 | 0.0178 | 0.6360 | 0.2638 | 0.085* | |
H8 | −0.0666 | 0.6418 | 0.2917 | 0.085* | |
H9 | 0.0038 | 0.7562 | 0.3131 | 0.085* | |
H10 | 0.0372 | 0.7254 | 0.4441 | 0.059* | |
H11 | 0.0976 | 0.7184 | 0.5687 | 0.052* | |
H12 | 0.1853 | 0.4819 | 0.6252 | 0.055* | |
H13 | 0.1765 | 0.5733 | 0.7329 | 0.065* | |
H14 | 0.1356 | 0.7079 | 0.6957 | 0.065* | |
H15 | 0.2784 | 0.7632 | 0.6820 | 0.071* | |
H16 | 0.2672 | 0.7731 | 0.7601 | 0.071* | |
H17 | 0.3940 | 0.6734 | 0.7733 | 0.067* | |
H18 | 0.3313 | 0.5533 | 0.7791 | 0.067* | |
H19 | 0.3371 | 0.4802 | 0.6634 | 0.055* | |
H20 | 0.4899 | 0.6269 | 0.7078 | 0.056* | |
H21 | 0.6044 | 0.5764 | 0.6565 | 0.063* | |
H22 | 0.7229 | 0.5522 | 0.5970 | 0.094* | |
H23 | 0.7041 | 0.4720 | 0.5247 | 0.094* | |
H24 | 0.7420 | 0.3957 | 0.5969 | 0.094* | |
H25 | 0.5880 | 0.2872 | 0.5059 | 0.064* | |
H26 | 0.4622 | 0.1607 | 0.4588 | 0.061* | |
H27 | 0.3867 | −0.0312 | 0.4363 | 0.085* | |
H28 | 0.3234 | 0.0735 | 0.3886 | 0.085* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Sm1 | 0.0310 (2) | 0.0294 (2) | 0.0415 (2) | −0.0005 (2) | 0.0072 (2) | −0.0003 (2) |
O1 | 0.036 (3) | 0.047 (3) | 0.049 (3) | −0.005 (2) | 0.016 (2) | −0.010 (3) |
O2 | 0.044 (3) | 0.037 (3) | 0.034 (3) | 0.000 (2) | 0.005 (2) | 0.002 (3) |
O3 | 0.054 (4) | 0.051 (3) | 0.064 (5) | −0.003 (3) | −0.001 (3) | 0.002 (3) |
O4 | 0.051 (4) | 0.047 (3) | 0.063 (4) | −0.006 (3) | 0.005 (3) | −0.002 (3) |
O5 | 0.064 (4) | 0.081 (5) | 0.105 (7) | 0.029 (4) | 0.000 (4) | 0.008 (5) |
O6 | 0.043 (3) | 0.040 (3) | 0.088 (5) | 0.004 (3) | 0.021 (3) | −0.006 (3) |
O7 | 0.046 (3) | 0.040 (3) | 0.112 (6) | 0.004 (3) | 0.029 (4) | 0.000 (3) |
O8 | 0.053 (4) | 0.063 (4) | 0.25 (1) | −0.023 (3) | 0.078 (5) | −0.015 (5) |
O9 | 0.089 (5) | 0.049 (3) | 0.062 (5) | 0.011 (3) | 0.023 (4) | 0.012 (3) |
O10 | 0.142 (7) | 0.097 (6) | 0.044 (4) | 0.008 (5) | 0.049 (4) | 0.002 (4) |
O11 | 0.061 (4) | 0.044 (3) | 0.049 (4) | −0.006 (3) | 0.017 (3) | −0.001 (3) |
N1 | 0.048 (4) | 0.041 (4) | 0.051 (5) | 0.010 (3) | 0.017 (3) | −0.004 (3) |
N2 | 0.033 (3) | 0.034 (3) | 0.056 (5) | −0.005 (3) | 0.007 (3) | −0.012 (3) |
N3 | 0.038 (4) | 0.050 (4) | 0.044 (4) | 0.000 (3) | 0.012 (3) | −0.012 (3) |
N4 | 0.039 (4) | 0.052 (4) | 0.045 (4) | −0.009 (3) | 0.008 (3) | −0.011 (3) |
N5 | 0.043 (4) | 0.052 (4) | 0.051 (5) | 0.007 (4) | 0.002 (4) | 0.000 (4) |
N6 | 0.039 (4) | 0.034 (4) | 0.113 (7) | −0.005 (3) | 0.021 (4) | 0.001 (4) |
N7 | 0.054 (4) | 0.050 (4) | 0.061 (5) | 0.012 (4) | 0.019 (4) | 0.005 (4) |
C1 | 0.063 (6) | 0.064 (6) | 0.107 (9) | 0.008 (5) | 0.019 (6) | −0.055 (5) |
C2 | 0.060 (6) | 0.048 (5) | 0.060 (6) | −0.003 (4) | 0.012 (5) | −0.022 (5) |
C3 | 0.031 (4) | 0.048 (4) | 0.055 (6) | 0.005 (4) | 0.010 (4) | −0.011 (4) |
C4 | 0.019 (3) | 0.051 (5) | 0.036 (5) | 0.010 (3) | 0.000 (3) | 0.007 (4) |
C5 | 0.035 (4) | 0.059 (5) | 0.050 (6) | 0.000 (4) | 0.006 (4) | −0.007 (5) |
C6 | 0.042 (5) | 0.051 (5) | 0.054 (6) | 0.000 (4) | 0.017 (4) | 0.005 (4) |
C7 | 0.078 (7) | 0.066 (6) | 0.061 (7) | 0.011 (5) | 0.004 (6) | 0.021 (6) |
C8 | 0.041 (5) | 0.039 (4) | 0.067 (6) | 0.011 (4) | 0.013 (4) | 0.015 (4) |
C9 | 0.021 (3) | 0.029 (4) | 0.048 (5) | 0.003 (3) | 0.007 (3) | 0.003 (3) |
C10 | 0.021 (3) | 0.031 (4) | 0.042 (5) | −0.006 (3) | 0.006 (3) | 0.008 (3) |
C11 | 0.043 (4) | 0.035 (4) | 0.055 (6) | 0.003 (3) | 0.019 (4) | 0.004 (4) |
C12 | 0.066 (6) | 0.050 (5) | 0.051 (6) | 0.005 (4) | 0.026 (4) | −0.004 (4) |
C13 | 0.075 (6) | 0.045 (5) | 0.062 (6) | 0.000 (5) | 0.028 (5) | −0.014 (5) |
C14 | 0.060 (6) | 0.054 (5) | 0.052 (6) | −0.006 (5) | 0.013 (5) | −0.014 (5) |
C15 | 0.038 (5) | 0.050 (5) | 0.043 (5) | −0.004 (4) | −0.006 (4) | 0.002 (4) |
C16 | 0.027 (4) | 0.054 (5) | 0.046 (5) | −0.011 (4) | 0.003 (4) | 0.007 (4) |
C17 | 0.039 (5) | 0.053 (5) | 0.062 (6) | −0.015 (4) | 0.005 (4) | 0.006 (5) |
C18 | 0.034 (4) | 0.059 (5) | 0.072 (7) | −0.008 (4) | 0.016 (4) | 0.006 (5) |
C19 | 0.039 (5) | 0.081 (7) | 0.123 (9) | −0.015 (5) | 0.037 (5) | 0.008 (7) |
C20 | 0.041 (4) | 0.071 (6) | 0.055 (5) | 0.006 (4) | 0.025 (4) | 0.009 (5) |
C21 | 0.037 (4) | 0.046 (4) | 0.051 (6) | 0.006 (4) | 0.010 (4) | 0.008 (4) |
C22 | 0.030 (4) | 0.044 (4) | 0.049 (5) | −0.006 (3) | 0.013 (4) | 0.006 (4) |
C23 | 0.044 (5) | 0.070 (6) | 0.044 (5) | −0.005 (4) | 0.020 (4) | −0.010 (4) |
C24 | 0.066 (6) | 0.082 (7) | 0.073 (7) | −0.005 (5) | 0.030 (5) | −0.025 (6) |
Geometric parameters (Å, º) top
Sm1—O1 | 2.335 (5) | C7—H8 | 0.95 |
Sm1—O2 | 2.346 (5) | C7—H9 | 0.95 |
Sm1—O3 | 2.628 (6) | C8—C9 | 1.41 (1) |
Sm1—O4 | 2.616 (6) | C8—H10 | 0.95 |
Sm1—O6 | 2.563 (5) | C9—C10 | 1.46 (1) |
Sm1—O7 | 2.604 (6) | C9—C11 | 1.40 (1) |
Sm1—O9 | 2.641 (7) | C11—H11 | 0.95 |
Sm1—O11 | 2.552 (6) | C12—C13 | 1.53 (1) |
Sm1—N2 | 2.598 (7) | C12—H13 | 0.95 |
Sm1—N3 | 2.634 (7) | C12—H14 | 0.95 |
O1—C22 | 1.294 (9) | C13—C14 | 1.50 (1) |
O2—C10 | 1.281 (9) | C13—H15 | 0.95 |
O3—N5 | 1.242 (9) | C13—H16 | 0.95 |
O4—N5 | 1.253 (8) | C14—H17 | 0.95 |
O5—N5 | 1.220 (9) | C14—H18 | 0.95 |
O6—N6 | 1.254 (9) | C15—C16 | 1.43 (1) |
O7—N6 | 1.254 (8) | C15—H20 | 0.95 |
O8—N6 | 1.189 (9) | C16—C17 | 1.40 (1) |
O9—N7 | 1.25 (1) | C16—C22 | 1.43 (1) |
O10—N7 | 1.22 (1) | C17—C18 | 1.37 (1) |
O11—N7 | 1.265 (9) | C17—H21 | 0.95 |
N1—C11 | 1.30 (1) | C18—C19 | 1.55 (1) |
N1—C12 | 1.47 (1) | C18—C20 | 1.37 (1) |
N1—H12 | 0.95 | C19—H22 | 0.95 |
N2—C2 | 1.48 (1) | C19—H23 | 0.95 |
N2—C3 | 1.28 (1) | C19—H24 | 0.95 |
N3—C23 | 1.26 (1) | C20—C21 | 1.42 (1) |
N3—C24 | 1.48 (1) | C20—H25 | 0.95 |
N4—C14 | 1.45 (1) | C21—C22 | 1.41 (1) |
N4—C15 | 1.28 (1) | C21—C23 | 1.45 (1) |
N4—H19 | 0.95 | C23—H26 | 0.95 |
C1—C2 | 1.47 (1) | C24—H27 | 0.95 |
C1—C24 | 1.45 (1) | C24—H28 | 0.95 |
C1—H1 | 0.95 | H1—H2 | 1.55 |
C1—H2 | 0.95 | H3—H4 | 1.55 |
C2—H3 | 0.95 | H7—H8 | 1.55 |
C2—H4 | 0.95 | H7—H9 | 1.55 |
C3—C4 | 1.46 (1) | H8—H9 | 1.55 |
C3—H5 | 0.95 | H13—H14 | 1.55 |
C4—C5 | 1.39 (1) | H15—H16 | 1.55 |
C4—C10 | 1.41 (1) | H17—H18 | 1.55 |
C5—C6 | 1.38 (1) | H22—H23 | 1.55 |
C5—H6 | 0.95 | H22—H24 | 1.55 |
C6—C7 | 1.53 (1) | H23—H24 | 1.55 |
C6—C8 | 1.39 (1) | H27—H28 | 1.55 |
C7—H7 | 0.95 | | |
| | | |
O1—Sm1—O2 | 72.2 (2) | C24—C2—H4 | 102.0 |
O1—Sm1—O3 | 68.1 (2) | C24—C2—H5 | 107.2 |
O1—Sm1—O4 | 111.2 (2) | H2—C2—H3 | 101.4 |
O1—Sm1—O6 | 175.1 (2) | H3—C2—H4 | 109.5 |
O1—Sm1—O7 | 134.2 (2) | N2—C3—C4 | 129.7 (6) |
O1—Sm1—O9 | 106.8 (2) | N2—C3—C10 | 101.3 (4) |
O1—Sm1—O11 | 71.1 (2) | N2—C3—H5 | 115.2 |
O1—Sm1—N2 | 110.9 (2) | C4—C3—H5 | 115.2 |
O1—Sm1—N3 | 70.6 (2) | O2—C4—C6 | 118.2 (3) |
O2—Sm1—O3 | 137.5 (2) | N2—C4—C9 | 130.6 (3) |
O2—Sm1—O4 | 173.6 (2) | N2—C4—C10 | 99.1 (4) |
O2—Sm1—O6 | 112.2 (2) | N2—C4—H6 | 116.7 |
O2—Sm1—O7 | 68.7 (2) | C3—C4—C5 | 118.2 (5) |
O2—Sm1—O9 | 110.5 (2) | C3—C4—C10 | 122.4 (5) |
O2—Sm1—O11 | 69.0 (2) | C5—C4—C10 | 119.4 (5) |
O2—Sm1—N2 | 70.6 (2) | C6—C4—H5 | 121.3 |
O2—Sm1—N3 | 107.0 (2) | C9—C4—H6 | 112.7 |
O3—Sm1—O4 | 47.8 (2) | C3—C5—C8 | 124.8 (3) |
O3—Sm1—O6 | 107.1 (2) | C4—C5—C6 | 124.2 (6) |
O3—Sm1—O7 | 134.8 (2) | C4—C5—H6 | 117.9 |
O3—Sm1—O9 | 68.4 (2) | C6—C5—C10 | 93.5 (4) |
O3—Sm1—O11 | 84.1 (2) | C6—C5—H6 | 117.9 |
O3—Sm1—N2 | 138.5 (2) | C7—C5—C10 | 124.2 (3) |
O3—Sm1—N3 | 73.7 (2) | C4—C6—H10 | 114.0 |
O4—Sm1—O6 | 64.5 (2) | C5—C6—C7 | 121.5 (6) |
O4—Sm1—O7 | 110.2 (2) | C5—C6—C8 | 117.5 (6) |
O4—Sm1—O9 | 74.0 (2) | C5—C6—H8 | 115.9 |
O4—Sm1—O11 | 117.0 (2) | C5—C6—H9 | 144.0 |
O4—Sm1—N2 | 103.0 (2) | C5—C6—H10 | 141.8 |
O4—Sm1—N3 | 70.1 (2) | C7—C6—C8 | 121.0 (6) |
O6—Sm1—O7 | 48.7 (2) | C8—C6—H8 | 119.8 |
O6—Sm1—O9 | 70.1 (2) | C9—C6—H6 | 112.7 |
O6—Sm1—O11 | 108.2 (2) | C9—C6—H9 | 125.4 |
O6—Sm1—N2 | 73.0 (2) | H6—C6—H9 | 120.2 |
O6—Sm1—N3 | 109.1 (2) | H7—C6—H10 | 117.9 |
O7—Sm1—O9 | 67.2 (2) | C5—C7—H8 | 104.9 |
O7—Sm1—O11 | 73.2 (2) | C6—C7—H7 | 109.5 |
O7—Sm1—N2 | 77.5 (2) | C6—C7—H8 | 109.5 |
O7—Sm1—N3 | 143.9 (2) | C6—C7—H9 | 109.5 |
O9—Sm1—O11 | 48.6 (2) | C8—C7—H7 | 130.9 |
O9—Sm1—N2 | 140.2 (2) | C8—C7—H8 | 109.5 |
O9—Sm1—N3 | 139.4 (2) | H7—C7—H8 | 109.5 |
O11—Sm1—N2 | 136.4 (2) | H7—C7—H9 | 109.5 |
O11—Sm1—N3 | 140.7 (2) | H8—C7—H9 | 109.5 |
N2—Sm1—N3 | 67.8 (2) | C6—C8—C9 | 121.8 (5) |
Sm1—O1—C21 | 111.3 (2) | C6—C8—C10 | 91.2 (4) |
Sm1—O1—C22 | 138.1 (3) | C6—C8—C11 | 152.3 (4) |
Sm1—O2—N1 | 127.3 (2) | C6—C8—H10 | 119.1 |
Sm1—O2—C4 | 113.2 (2) | C7—C8—C11 | 175.7 (3) |
Sm1—O2—C9 | 171.5 (2) | C9—C8—H10 | 119.1 |
Sm1—O2—C10 | 142.7 (4) | O2—C9—H11 | 118.1 |
N1—O2—C4 | 119.3 (2) | N1—C9—H10 | 121.2 |
N1—O2—C9 | 57.0 (2) | C4—C9—H10 | 112.2 |
N1—O2—C10 | 89.5 (3) | C4—C9—H12 | 104.7 |
Sm1—O3—N5 | 97.6 (3) | C6—C9—H11 | 122.7 |
Sm1—O3—H20i | 138.4 | C8—C9—C10 | 119.3 (5) |
O4—O3—O5 | 60.5 (2) | C8—C9—C11 | 118.6 (5) |
O4—O3—H20i | 130.0 | O2—C10—C4 | 123.4 (5) |
O5—O3—H20i | 83.3 | O2—C10—C9 | 119.0 (5) |
N5—O3—H20i | 106.6 | C3—C10—C8 | 116.7 (3) |
Sm1—O4—N5 | 97.5 (3) | C4—C10—C9 | 117.6 (5) |
Sm1—O4—H1 | 79.9 | C8—C10—H12 | 103.4 |
Sm1—O4—H15ii | 111.8 | N1—C11—H11 | 117.7 |
O3—O4—H1 | 129.1 | C9—C11—H11 | 117.7 |
O3—O4—H15ii | 118.9 | N1—C12—C13 | 114.6 (5) |
O5—O4—H15ii | 96.9 | N1—C12—C14 | 103.7 (4) |
N5—O4—H1 | 139.9 | N1—C12—H13 | 108.2 |
N5—O4—H15ii | 109.8 | N1—C12—H14 | 108.2 |
H1—O4—H15ii | 108.2 | C11—C12—C13 | 114.7 (5) |
Sm1—O6—O7 | 66.5 (1) | C11—C12—C14 | 118.2 (3) |
Sm1—O6—O8 | 126.2 (2) | C11—C12—H13 | 127.7 |
Sm1—O6—H11ii | 169.9 | C13—C12—H11 | 110.7 |
O7—O6—H11ii | 123.6 | C13—C12—H12 | 109.9 |
O8—O7—H10iii | 97.8 | C13—C12—H13 | 108.2 |
N6—O7—H10iii | 122.2 | C13—C12—H14 | 108.2 |
O6—O8—H11ii | 63.9 | C14—C12—H11 | 126.7 |
O7—O8—H11ii | 123.2 | H11—C12—H16 | 118.2 |
N6—O8—H11ii | 93.7 | H12—C12—H14 | 129.2 |
O10—O9—O11 | 60.1 (2) | H13—C12—H14 | 109.5 |
O9—O10—O11 | 59.3 (2) | N4—C13—C12 | 105.3 (4) |
Sm1—O11—O10 | 128.1 (2) | C12—C13—C14 | 116.4 (5) |
C9—N1—C12 | 153.4 (4) | C12—C13—H15 | 107.7 |
C9—N1—C13 | 140.8 (3) | C12—C13—H16 | 107.7 |
C9—N1—H14 | 127.7 | C14—C13—H15 | 107.7 |
C9—N1—H15 | 119.5 | C14—C13—H16 | 107.7 |
C11—N1—C12 | 124.3 (5) | H13—C13—H17 | 118.0 |
C11—N1—C13 | 121.4 (4) | H14—C13—H18 | 117.6 |
C12—N1—H12 | 117.9 | H15—C13—H16 | 109.5 |
C13—N1—H11 | 100.4 | N4—C14—H17 | 107.9 |
C13—N1—H12 | 109.7 | N4—C14—H18 | 107.9 |
H11—N1—H12 | 143.8 | C13—C14—H17 | 107.9 |
H11—N1—H13 | 119.2 | C13—C14—H18 | 107.9 |
H11—N1—H14 | 73.8 | C15—C14—H18 | 119.3 |
H11—N1—H15 | 85.9 | H17—C14—H18 | 109.5 |
H12—N1—H13 | 95.5 | N4—C15—H20 | 117.3 |
H12—N1—H14 | 141.4 | C16—C15—H20 | 117.3 |
H12—N1—H15 | 116.2 | O1—C16—C18 | 120.5 (3) |
Sm1—N2—C1 | 90.2 (2) | O1—C16—H20 | 117.6 |
Sm1—N2—C2 | 115.4 (3) | N4—C16—H21 | 119.5 |
Sm1—N2—C3 | 129.4 (4) | C15—C16—C17 | 117.8 (5) |
Sm1—N2—H3 | 106.9 | C15—C16—C22 | 121.6 (5) |
C1—N2—C3 | 132.8 (5) | C17—C16—C22 | 120.6 (6) |
C1—N2—C4 | 152.7 (3) | C18—C16—H20 | 121.8 |
C1—N2—H5 | 108.6 | C21—C16—H19 | 105.5 |
C2—N2—C3 | 115.0 (5) | C15—C17—C20 | 122.5 (3) |
C3—N2—H3 | 120.3 | C16—C17—C18 | 122.3 (6) |
C3—N2—H4 | 88.6 | C16—C17—H21 | 118.8 |
C4—N2—H4 | 115.5 | C18—C17—H21 | 118.8 |
Sm1—N3—C21 | 99.8 (2) | C16—C18—H25 | 113.0 |
Sm1—N3—C23 | 127.0 (4) | C17—C18—C19 | 122.1 (6) |
Sm1—N3—C24 | 119.6 (4) | C17—C18—C20 | 117.8 (6) |
C1—N3—C21 | 170.3 (3) | C20—C18—H23 | 100.4 |
C1—N3—C23 | 143.6 (5) | C20—C18—H24 | 110.9 |
C1—N3—H26 | 116.6 | C21—C18—H21 | 113.6 |
C21—N3—H27 | 120.4 | C21—C18—H23 | 127.6 |
C21—N3—H28 | 125.0 | H21—C18—H23 | 114.8 |
C23—N3—C24 | 113.3 (5) | H21—C18—H24 | 103.6 |
C23—N3—H27 | 94.9 | C17—C19—H23 | 126.3 |
C23—N3—H28 | 101.0 | C17—C19—H24 | 114.7 |
H1—N3—H26 | 125.3 | C18—C19—H22 | 109.5 |
C13—N4—H20 | 110.3 | C18—C19—H23 | 109.5 |
C14—N4—C15 | 123.7 (5) | C18—C19—H24 | 109.5 |
C14—N4—C16 | 152.3 (4) | H22—C19—H23 | 109.5 |
C14—N4—H19 | 118.2 | H22—C19—H24 | 109.5 |
C15—N4—H15 | 117.6 | H23—C19—H24 | 109.5 |
C15—N4—H17 | 96.4 | C17—C20—C23 | 124.2 (3) |
C15—N4—H18 | 133.4 | C18—C20—C21 | 123.1 (6) |
C15—N4—H19 | 118.2 | C18—C20—H25 | 118.4 |
C16—N4—H17 | 125.0 | C21—C20—H25 | 118.4 |
H15—N4—H20 | 100.5 | O1—C21—C18 | 118.5 (3) |
H18—N4—H19 | 102.3 | O1—C21—H26 | 120.4 |
H18—N4—H20 | 111.6 | N3—C21—C22 | 100.6 (4) |
O3—N5—O4 | 116.9 (5) | N3—C21—H25 | 116.3 |
O3—N5—O5 | 121.5 (5) | C16—C21—H25 | 111.5 |
O4—N5—O5 | 121.6 (5) | C18—C21—H26 | 120.7 |
O6—N6—O7 | 116.8 (5) | C20—C21—C22 | 118.9 (5) |
O6—N6—O8 | 121.5 (5) | C20—C21—C23 | 117.2 (6) |
O7—N6—O8 | 121.7 (5) | C22—C21—C23 | 123.8 (5) |
O9—N7—O10 | 122.8 (6) | O1—C22—C16 | 120.4 (5) |
O9—N7—O11 | 116.3 (6) | O1—C22—C21 | 122.4 (5) |
O10—N7—O11 | 120.9 (5) | C15—C22—C20 | 115.8 (3) |
N3—C1—C2 | 104.9 (4) | C16—C22—C21 | 117.2 (5) |
C2—C1—C24 | 120.2 (6) | C17—C22—C23 | 116.4 (3) |
C2—C1—H1 | 106.7 | N3—C23—C21 | 129.1 (6) |
C2—C1—H2 | 106.7 | N3—C23—C22 | 102.0 (4) |
C2—C1—H28 | 101.8 | N3—C23—H26 | 115.4 |
C24—C1—H1 | 106.7 | C21—C23—H26 | 115.4 |
C24—C1—H2 | 106.7 | H25—C23—H27 | 122.2 |
C24—C1—H3 | 144.7 | N3—C24—C1 | 117.3 (6) |
C24—C1—H4 | 113.1 | N3—C24—C2 | 103.3 (4) |
H1—C1—H2 | 109.5 | N3—C24—H27 | 107.5 |
N2—C2—C1 | 113.4 (5) | N3—C24—H28 | 107.5 |
N2—C2—H1 | 107.3 | C1—C24—H27 | 107.5 |
N2—C2—H3 | 108.5 | C1—C24—H28 | 107.5 |
N2—C2—H4 | 108.5 | H27—C24—H28 | 109.5 |
C3—C2—C24 | 100.8 (3) | | |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, y−1, z; (iii) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O2 | 0.95 | 1.90 | 2.619 (6) | 131 |
N1—H12···O11 | 0.95 | 2.26 | 3.082 (10) | 145 |
N4—H19···O1 | 0.95 | 1.94 | 2.655 (6) | 130 |
N4—H19···O11 | 0.95 | 2.34 | 3.063 (10) | 132 |