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The new Schiff base ligand,
N,
N′-bis(5-methylsalicylidene)-4-methyl-1,3-phenylenediamine (H
2L), has been prepared by condensation of 5-methylsalicylaldehyde with 4-methyl-1,3-phenylenediamine. It was found that this ligand crystallizes in the monoclinic space group
P2
1/
c, with
Z′ = 1. Further studies showed that – as a result of the one-pot metal-promoted reactions – three different polymorphic forms of H
2L were obtained, with different numbers (1, 3 or 4) of symmetry-independent molecules depending on the lanthanide metal ion present in the reaction media: La (
Z′ = 3), Nd (
Z′ = 4), Sm, Tb, Ho and Yb (all
Z′ = 1); the last form is identical with that obtained by crystallization of the ligand itself. The geometrical features of all eight independent molecules of H
2L are very similar. The relatively strong intramolecular O—H
N hydrogen bonds stabilize almost co-planar conformations of terminal rings and C—C=N—C linkers, at the same time strong hydrogen-bond donors and acceptors involved in these interactions cannot take part in the determination of supramolecular architecture. Therefore, weak intermolecular interactions are important and this can be regarded as one of the reasons for packing conflicts that lead to the presence of polymorphic forms and multiple molecules. The pseudosymmetries are observed in both forms with
Z′ > 1 and the degree of pseudosymmetry is described by the values of appropriate combinations of the coordinates. In order to elucidate the differences in crystal structures the Hirshfeld surface method was applied. It shows that there are only small differences in the surface shape and in the fingerprint plots; however, the volumes of voids in three structures are significantly different.
Supporting information
CCDC references: 965026; 965027
Crystal data, data collection and structure refinement details are summarized
in Table 1.
S2. Results and discussion
top
For all compounds, data collection: CrysAlis PRO (Agilent Technologies (2011)); cell refinement: CrysAlis PRO (Agilent Technologies (2011)); data reduction: CrysAlis PRO (Agilent Technologies (2011)); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013); molecular graphics: Mercury (McRae et al., 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2013).
Crystal data top
C23H22N2O2 | F(000) = 760 |
Mr = 358.42 | Dx = 1.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.810 (2) Å | Cell parameters from 2341 reflections |
b = 20.601 (3) Å | θ = 2.2–27.0° |
c = 18.831 (3) Å | µ = 0.08 mm−1 |
β = 91.95 (2)° | T = 295 K |
V = 1864.9 (9) Å3 | Prism, red |
Z = 4 | 0.35 × 0.2 × 0.1 mm |
Data collection top
Xcalibur, Sapphire2, large Be window diffractometer | 3286 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1408 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.088 |
Detector resolution: 8.1929 pixels mm-1 | θmax = 25.0°, θmin = 2.9° |
ω–scan | h = −5→5 |
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −24→24 |
Tmin = 0.920, Tmax = 1.000 | l = −22→22 |
20558 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.078 | H-atom parameters constrained |
wR(F2) = 0.192 | w = 1/[σ2(Fo2) + (0.054P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
3286 reflections | Δρmax = 0.23 e Å−3 |
251 parameters | Δρmin = −0.29 e Å−3 |
Crystal data top
C23H22N2O2 | V = 1864.9 (9) Å3 |
Mr = 358.42 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 4.810 (2) Å | µ = 0.08 mm−1 |
b = 20.601 (3) Å | T = 295 K |
c = 18.831 (3) Å | 0.35 × 0.2 × 0.1 mm |
β = 91.95 (2)° | |
Data collection top
Xcalibur, Sapphire2, large Be window diffractometer | 3286 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 1408 reflections with I > 2σ(I) |
Tmin = 0.920, Tmax = 1.000 | Rint = 0.088 |
20558 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.192 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.23 e Å−3 |
3286 reflections | Δρmin = −0.29 e Å−3 |
251 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.7953 (7) | 0.25676 (17) | 0.70651 (19) | 0.0497 (10) | |
C2 | 0.9292 (7) | 0.31344 (18) | 0.69061 (19) | 0.0543 (10) | |
H2 | 0.8821 | 0.3344 | 0.6482 | 0.065* | |
C3 | 1.1340 (7) | 0.34087 (18) | 0.7358 (2) | 0.0532 (10) | |
C4 | 1.2038 (8) | 0.3106 (2) | 0.7998 (2) | 0.0571 (11) | |
C41 | 1.4152 (8) | 0.33892 (19) | 0.8513 (2) | 0.0758 (13) | |
H413 | 1.5848 | 0.3472 | 0.8274 | 0.114* | |
H412 | 1.4507 | 0.3089 | 0.8896 | 0.114* | |
H411 | 1.3455 | 0.3789 | 0.8700 | 0.114* | |
C5 | 1.0669 (8) | 0.25315 (19) | 0.8149 (2) | 0.0642 (12) | |
H5 | 1.1121 | 0.2320 | 0.8574 | 0.077* | |
C6 | 0.8674 (8) | 0.22615 (18) | 0.7700 (2) | 0.0610 (11) | |
H6 | 0.7813 | 0.1875 | 0.7822 | 0.073* | |
N11 | 0.5866 (6) | 0.23598 (15) | 0.65678 (15) | 0.0527 (8) | |
C12 | 0.4709 (7) | 0.18069 (18) | 0.66149 (18) | 0.0524 (10) | |
H12 | 0.5290 | 0.1528 | 0.6979 | 0.063* | |
C13 | 0.2524 (7) | 0.15984 (17) | 0.61228 (18) | 0.0483 (9) | |
C14 | 0.1599 (7) | 0.19820 (19) | 0.55564 (19) | 0.0523 (10) | |
O14 | 0.2735 (6) | 0.25714 (13) | 0.54310 (14) | 0.0729 (9) | |
H14 | 0.4234 | 0.2619 | 0.5801 | 0.087* | |
C15 | −0.0497 (8) | 0.1759 (2) | 0.51045 (19) | 0.0628 (11) | |
H15 | −0.1124 | 0.2015 | 0.4725 | 0.075* | |
C16 | −0.1663 (8) | 0.1164 (2) | 0.5210 (2) | 0.0624 (11) | |
H16 | −0.3067 | 0.1021 | 0.4896 | 0.075* | |
C17 | −0.0819 (8) | 0.07647 (18) | 0.5772 (2) | 0.0555 (10) | |
C171 | −0.2119 (8) | 0.01104 (19) | 0.5884 (2) | 0.0788 (13) | |
H17C | −0.2037 | −0.0140 | 0.5455 | 0.118* | |
H17B | −0.4026 | 0.0165 | 0.6007 | 0.118* | |
H17A | −0.1126 | −0.0112 | 0.6262 | 0.118* | |
C18 | 0.1261 (8) | 0.09974 (18) | 0.62136 (19) | 0.0554 (10) | |
H18 | 0.1864 | 0.0741 | 0.6595 | 0.067* | |
N31 | 1.2734 (6) | 0.39883 (17) | 0.71940 (18) | 0.0621 (9) | |
C32 | 1.2189 (12) | 0.4301 (3) | 0.6659 (3) | 0.141 (3) | |
H32 | 1.0798 | 0.4138 | 0.6354 | 0.169* | |
C33 | 1.3493 (10) | 0.4904 (2) | 0.6450 (3) | 0.0942 (16) | |
C34 | 1.5428 (12) | 0.5180 (3) | 0.6855 (3) | 0.0935 (16) | |
O34 | 1.6300 (10) | 0.4891 (2) | 0.7468 (2) | 0.165 (2) | |
H34 | 1.5902 | 0.4440 | 0.7440 | 0.198* | |
C35 | 1.6600 (15) | 0.5763 (3) | 0.6644 (3) | 0.146 (3) | |
H35 | 1.8009 | 0.5958 | 0.6919 | 0.175* | |
C36 | 1.5641 (14) | 0.6048 (2) | 0.6021 (3) | 0.1080 (19) | |
H36 | 1.6394 | 0.6446 | 0.5895 | 0.130* | |
C37 | 1.3749 (12) | 0.5794 (3) | 0.5600 (4) | 0.128 (2) | |
C371 | 1.2878 (16) | 0.6134 (4) | 0.4920 (4) | 0.231 (5) | |
H37C | 1.4423 | 0.6375 | 0.4747 | 0.346* | |
H37B | 1.1371 | 0.6426 | 0.5008 | 0.346* | |
H37A | 1.2285 | 0.5819 | 0.4571 | 0.346* | |
C38 | 1.2714 (14) | 0.5216 (3) | 0.5835 (4) | 0.197 (4) | |
H38 | 1.1351 | 0.5017 | 0.5549 | 0.237* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.046 (2) | 0.050 (2) | 0.053 (2) | 0.0046 (19) | −0.0048 (19) | −0.0084 (19) |
C2 | 0.051 (2) | 0.055 (3) | 0.057 (2) | 0.004 (2) | −0.006 (2) | −0.0018 (19) |
C3 | 0.045 (2) | 0.054 (3) | 0.060 (3) | 0.004 (2) | −0.006 (2) | −0.013 (2) |
C4 | 0.051 (2) | 0.061 (3) | 0.059 (3) | 0.013 (2) | −0.012 (2) | −0.017 (2) |
C41 | 0.070 (3) | 0.088 (3) | 0.068 (3) | 0.011 (2) | −0.021 (2) | −0.023 (2) |
C5 | 0.068 (3) | 0.062 (3) | 0.061 (3) | 0.017 (2) | −0.016 (2) | −0.004 (2) |
C6 | 0.068 (3) | 0.051 (2) | 0.063 (3) | 0.003 (2) | −0.010 (2) | −0.001 (2) |
N11 | 0.053 (2) | 0.054 (2) | 0.0515 (19) | −0.0015 (17) | −0.0059 (16) | −0.0073 (16) |
C12 | 0.053 (2) | 0.051 (3) | 0.052 (2) | 0.007 (2) | −0.003 (2) | 0.0007 (19) |
C13 | 0.046 (2) | 0.050 (2) | 0.049 (2) | −0.0020 (19) | −0.0035 (18) | −0.0001 (18) |
C14 | 0.050 (2) | 0.060 (3) | 0.047 (2) | −0.003 (2) | −0.001 (2) | 0.001 (2) |
O14 | 0.075 (2) | 0.0711 (19) | 0.0718 (19) | −0.0178 (16) | −0.0162 (15) | 0.0186 (15) |
C15 | 0.064 (3) | 0.075 (3) | 0.049 (2) | −0.006 (2) | −0.011 (2) | 0.011 (2) |
C16 | 0.055 (3) | 0.078 (3) | 0.054 (3) | −0.009 (2) | −0.007 (2) | −0.008 (2) |
C17 | 0.049 (2) | 0.057 (3) | 0.061 (3) | −0.005 (2) | 0.004 (2) | −0.006 (2) |
C171 | 0.075 (3) | 0.067 (3) | 0.095 (3) | −0.017 (2) | 0.005 (3) | −0.006 (2) |
C18 | 0.058 (3) | 0.055 (3) | 0.053 (2) | 0.002 (2) | −0.001 (2) | 0.0012 (19) |
N31 | 0.055 (2) | 0.067 (2) | 0.064 (2) | −0.0106 (19) | −0.0035 (18) | −0.0092 (18) |
C32 | 0.148 (6) | 0.118 (5) | 0.150 (5) | −0.082 (4) | −0.085 (5) | 0.049 (4) |
C33 | 0.080 (3) | 0.081 (4) | 0.120 (4) | −0.036 (3) | −0.034 (3) | 0.010 (3) |
C34 | 0.121 (4) | 0.099 (4) | 0.060 (3) | −0.041 (3) | 0.004 (3) | −0.023 (3) |
O34 | 0.226 (5) | 0.165 (4) | 0.101 (3) | −0.124 (4) | −0.056 (3) | 0.005 (3) |
C35 | 0.210 (7) | 0.124 (5) | 0.103 (5) | −0.117 (5) | −0.012 (5) | −0.017 (4) |
C36 | 0.154 (6) | 0.079 (4) | 0.093 (4) | −0.042 (4) | 0.040 (4) | −0.020 (3) |
C37 | 0.114 (5) | 0.112 (5) | 0.156 (6) | −0.057 (4) | −0.038 (4) | 0.026 (4) |
C371 | 0.241 (9) | 0.190 (7) | 0.252 (9) | −0.126 (7) | −0.125 (7) | 0.155 (7) |
C38 | 0.194 (7) | 0.163 (6) | 0.225 (8) | −0.125 (6) | −0.132 (6) | 0.120 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.371 (5) | C16—H16 | 0.9300 |
C1—C6 | 1.385 (5) | C17—C18 | 1.366 (5) |
C1—N11 | 1.416 (4) | C17—C171 | 1.504 (5) |
C2—C3 | 1.399 (5) | C171—H17C | 0.9600 |
C2—H2 | 0.9300 | C171—H17B | 0.9600 |
C3—C4 | 1.387 (5) | C171—H17A | 0.9600 |
C3—N31 | 1.409 (4) | C18—H18 | 0.9300 |
C4—C5 | 1.388 (5) | N31—C32 | 1.217 (5) |
C4—C41 | 1.500 (5) | C32—C33 | 1.451 (6) |
C41—H413 | 0.9600 | C32—H32 | 0.9300 |
C41—H412 | 0.9600 | C33—C34 | 1.313 (6) |
C41—H411 | 0.9600 | C33—C38 | 1.365 (6) |
C5—C6 | 1.375 (5) | C34—O34 | 1.353 (5) |
C5—H5 | 0.9300 | C34—C35 | 1.391 (6) |
C6—H6 | 0.9300 | O34—H34 | 0.9494 |
N11—C12 | 1.272 (4) | C35—C36 | 1.376 (7) |
C12—C13 | 1.443 (5) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—C37 | 1.297 (7) |
C13—C14 | 1.388 (4) | C36—H36 | 0.9300 |
C13—C18 | 1.392 (4) | C37—C38 | 1.370 (7) |
C14—O14 | 1.356 (4) | C37—C371 | 1.508 (7) |
C14—C15 | 1.376 (5) | C371—H37C | 0.9600 |
O14—H14 | 0.9898 | C371—H37B | 0.9600 |
C15—C16 | 1.366 (5) | C371—H37A | 0.9600 |
C15—H15 | 0.9300 | C38—H38 | 0.9300 |
C16—C17 | 1.389 (5) | | |
| | | |
C2—C1—C6 | 118.1 (3) | C18—C17—C16 | 116.4 (4) |
C2—C1—N11 | 116.1 (3) | C18—C17—C171 | 121.9 (4) |
C6—C1—N11 | 125.8 (3) | C16—C17—C171 | 121.7 (4) |
C1—C2—C3 | 122.5 (4) | C17—C171—H17C | 109.5 |
C1—C2—H2 | 118.8 | C17—C171—H17B | 109.5 |
C3—C2—H2 | 118.8 | H17C—C171—H17B | 109.5 |
C4—C3—C2 | 119.4 (4) | C17—C171—H17A | 109.5 |
C4—C3—N31 | 118.0 (4) | H17C—C171—H17A | 109.5 |
C2—C3—N31 | 122.6 (4) | H17B—C171—H17A | 109.5 |
C3—C4—C5 | 117.4 (3) | C17—C18—C13 | 123.4 (4) |
C3—C4—C41 | 121.7 (4) | C17—C18—H18 | 118.3 |
C5—C4—C41 | 121.0 (4) | C13—C18—H18 | 118.3 |
C4—C41—H413 | 109.5 | C32—N31—C3 | 122.7 (4) |
C4—C41—H412 | 109.5 | N31—C32—C33 | 126.5 (5) |
H413—C41—H412 | 109.5 | N31—C32—H32 | 116.7 |
C4—C41—H411 | 109.5 | C33—C32—H32 | 116.7 |
H413—C41—H411 | 109.5 | C34—C33—C38 | 117.2 (5) |
H412—C41—H411 | 109.5 | C34—C33—C32 | 121.2 (5) |
C6—C5—C4 | 122.9 (4) | C38—C33—C32 | 121.6 (5) |
C6—C5—H5 | 118.5 | C33—C34—O34 | 119.8 (5) |
C4—C5—H5 | 118.5 | C33—C34—C35 | 119.7 (5) |
C5—C6—C1 | 119.7 (4) | O34—C34—C35 | 120.5 (5) |
C5—C6—H6 | 120.1 | C34—O34—H34 | 109.2 |
C1—C6—H6 | 120.1 | C36—C35—C34 | 119.0 (5) |
C12—N11—C1 | 121.8 (3) | C36—C35—H35 | 120.5 |
N11—C12—C13 | 122.2 (3) | C34—C35—H35 | 120.5 |
N11—C12—H12 | 118.9 | C37—C36—C35 | 123.8 (5) |
C13—C12—H12 | 118.9 | C37—C36—H36 | 118.1 |
C14—C13—C18 | 118.1 (3) | C35—C36—H36 | 118.1 |
C14—C13—C12 | 122.1 (3) | C36—C37—C38 | 114.1 (6) |
C18—C13—C12 | 119.8 (3) | C36—C37—C371 | 120.0 (6) |
O14—C14—C15 | 118.9 (3) | C38—C37—C371 | 125.8 (6) |
O14—C14—C13 | 121.5 (3) | C37—C371—H37C | 109.5 |
C15—C14—C13 | 119.6 (4) | C37—C371—H37B | 109.5 |
C14—O14—H14 | 104.8 | H37C—C371—H37B | 109.5 |
C16—C15—C14 | 120.4 (4) | C37—C371—H37A | 109.5 |
C16—C15—H15 | 119.8 | H37C—C371—H37A | 109.5 |
C14—C15—H15 | 119.8 | H37B—C371—H37A | 109.5 |
C15—C16—C17 | 122.1 (4) | C33—C38—C37 | 126.2 (5) |
C15—C16—H16 | 118.9 | C33—C38—H38 | 116.9 |
C17—C16—H16 | 118.9 | C37—C38—H38 | 116.9 |
| | | |
C6—C1—C2—C3 | 0.1 (5) | C15—C16—C17—C18 | −0.4 (6) |
N11—C1—C2—C3 | 178.0 (3) | C15—C16—C17—C171 | 179.9 (4) |
C1—C2—C3—C4 | −0.8 (5) | C16—C17—C18—C13 | −0.2 (5) |
C1—C2—C3—N31 | 179.5 (3) | C171—C17—C18—C13 | 179.6 (4) |
C2—C3—C4—C5 | 1.0 (5) | C14—C13—C18—C17 | 0.6 (5) |
N31—C3—C4—C5 | −179.4 (3) | C12—C13—C18—C17 | −180.0 (3) |
C2—C3—C4—C41 | −178.0 (3) | C4—C3—N31—C32 | −177.2 (5) |
N31—C3—C4—C41 | 1.7 (5) | C2—C3—N31—C32 | 2.5 (7) |
C3—C4—C5—C6 | −0.5 (6) | C3—N31—C32—C33 | 179.5 (5) |
C41—C4—C5—C6 | 178.5 (3) | N31—C32—C33—C34 | −1.7 (11) |
C4—C5—C6—C1 | −0.2 (6) | N31—C32—C33—C38 | −180.0 (7) |
C2—C1—C6—C5 | 0.4 (5) | C38—C33—C34—O34 | −179.5 (6) |
N11—C1—C6—C5 | −177.3 (3) | C32—C33—C34—O34 | 2.1 (9) |
C2—C1—N11—C12 | 171.8 (3) | C38—C33—C34—C35 | −0.5 (9) |
C6—C1—N11—C12 | −10.5 (5) | C32—C33—C34—C35 | −178.9 (6) |
C1—N11—C12—C13 | 178.2 (3) | C33—C34—C35—C36 | 1.8 (9) |
N11—C12—C13—C14 | 1.7 (5) | O34—C34—C35—C36 | −179.2 (6) |
N11—C12—C13—C18 | −177.7 (3) | C34—C35—C36—C37 | −2.3 (11) |
C18—C13—C14—O14 | −179.7 (3) | C35—C36—C37—C38 | 1.4 (11) |
C12—C13—C14—O14 | 0.9 (5) | C35—C36—C37—C371 | −178.5 (7) |
C18—C13—C14—C15 | −0.4 (5) | C34—C33—C38—C37 | −0.4 (12) |
C12—C13—C14—C15 | −179.9 (3) | C32—C33—C38—C37 | 177.9 (7) |
O14—C14—C15—C16 | 179.2 (3) | C36—C37—C38—C33 | 0.0 (13) |
C13—C14—C15—C16 | −0.1 (6) | C371—C37—C38—C33 | 179.9 (8) |
C14—C15—C16—C17 | 0.5 (6) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N11 | 0.99 | 1.71 | 2.612 (4) | 150 |
O34—H34···N31 | 0.95 | 1.83 | 2.570 (5) | 132 |
C371—H37C···O14i | 0.96 | 2.59 | 3.477 (6) | 153 |
C18—H18···O34ii | 0.93 | 2.62 | 3.541 (5) | 172 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2. |
Crystal data top
C23H22N2O2 | F(000) = 2280 |
Mr = 358.42 | Dx = 1.233 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 21.694 (3) Å | Cell parameters from 5042 reflections |
b = 12.599 (2) Å | θ = 2.8–74.1° |
c = 21.236 (3) Å | µ = 0.63 mm−1 |
β = 93.38 (2)° | T = 295 K |
V = 5794.2 (15) Å3 | Needle, yellow |
Z = 12 | 0.25 × 0.1 × 0.1 mm |
Data collection top
SuperNova, Single source at offset), Atlas diffractometer | 10386 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 5091 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.043 |
Detector resolution: 10.5357 pixels mm-1 | θmax = 67.5°, θmin = 4.1° |
ω–scan | h = −25→25 |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −14→15 |
Tmin = 0.332, Tmax = 1.000 | l = −20→25 |
28367 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.078 | H-atom parameters constrained |
wR(F2) = 0.220 | w = 1/[σ2(Fo2) + (0.080P)2 + 0.750P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.003 |
10386 reflections | Δρmax = 0.29 e Å−3 |
745 parameters | Δρmin = −0.21 e Å−3 |
Crystal data top
C23H22N2O2 | V = 5794.2 (15) Å3 |
Mr = 358.42 | Z = 12 |
Monoclinic, P21/c | Cu Kα radiation |
a = 21.694 (3) Å | µ = 0.63 mm−1 |
b = 12.599 (2) Å | T = 295 K |
c = 21.236 (3) Å | 0.25 × 0.1 × 0.1 mm |
β = 93.38 (2)° | |
Data collection top
SuperNova, Single source at offset), Atlas diffractometer | 10386 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 5091 reflections with I > 2σ(I) |
Tmin = 0.332, Tmax = 1.000 | Rint = 0.043 |
28367 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.078 | 0 restraints |
wR(F2) = 0.220 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.29 e Å−3 |
10386 reflections | Δρmin = −0.21 e Å−3 |
745 parameters | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1A | 0.67523 (13) | 0.8291 (3) | 0.89295 (16) | 0.0776 (9) | |
C2A | 0.62963 (14) | 0.7552 (3) | 0.90060 (16) | 0.0801 (9) | |
H2A | 0.6398 | 0.6834 | 0.9007 | 0.096* | |
C3A | 0.56844 (14) | 0.7850 (3) | 0.90821 (16) | 0.0762 (8) | |
C4A | 0.55243 (15) | 0.8919 (3) | 0.90822 (17) | 0.0816 (9) | |
C41A | 0.48713 (15) | 0.9277 (3) | 0.9175 (2) | 0.0975 (11) | |
H41A | 0.4757 | 0.9074 | 0.9588 | 0.146* | |
H41B | 0.4595 | 0.8950 | 0.8862 | 0.146* | |
H41C | 0.4846 | 1.0035 | 0.9133 | 0.146* | |
C5A | 0.59849 (16) | 0.9662 (3) | 0.89907 (19) | 0.0944 (11) | |
H5A | 0.5884 | 1.0380 | 0.8980 | 0.113* | |
C6A | 0.65879 (15) | 0.9361 (3) | 0.89157 (18) | 0.0906 (10) | |
H6A | 0.6886 | 0.9875 | 0.8856 | 0.109* | |
N11A | 0.73558 (12) | 0.7898 (2) | 0.88599 (13) | 0.0828 (8) | |
C12A | 0.78396 (14) | 0.8489 (3) | 0.89778 (17) | 0.0825 (9) | |
H12A | 0.7787 | 0.9181 | 0.9118 | 0.099* | |
C13A | 0.84589 (14) | 0.8099 (3) | 0.88967 (16) | 0.0745 (8) | |
C14A | 0.85597 (15) | 0.7053 (3) | 0.87067 (17) | 0.0820 (9) | |
O14A | 0.80901 (11) | 0.63621 (18) | 0.85715 (15) | 0.1024 (8) | |
H14A | 0.7760 | 0.6656 | 0.8622 | 0.123* | |
C15A | 0.91644 (17) | 0.6698 (3) | 0.86396 (19) | 0.0973 (11) | |
H15A | 0.9238 | 0.6010 | 0.8503 | 0.117* | |
C16A | 0.96512 (17) | 0.7389 (3) | 0.87798 (19) | 0.0989 (12) | |
H16A | 1.0052 | 0.7146 | 0.8743 | 0.119* | |
C17A | 0.95630 (15) | 0.8421 (3) | 0.89719 (18) | 0.0904 (10) | |
C171 | 1.00992 (16) | 0.9160 (3) | 0.9114 (2) | 0.1182 (14) | |
H17A | 0.9954 | 0.9800 | 0.9301 | 0.177* | |
H17B | 1.0290 | 0.9328 | 0.8730 | 0.177* | |
H17C | 1.0395 | 0.8822 | 0.9402 | 0.177* | |
C18A | 0.89610 (14) | 0.8758 (3) | 0.90283 (17) | 0.0845 (10) | |
H18A | 0.8892 | 0.9450 | 0.9159 | 0.101* | |
N31A | 0.52047 (11) | 0.7107 (2) | 0.91718 (14) | 0.0795 (7) | |
C32A | 0.52706 (14) | 0.6111 (3) | 0.90975 (16) | 0.0787 (9) | |
H32A | 0.5645 | 0.5859 | 0.8966 | 0.094* | |
C33A | 0.47857 (13) | 0.5352 (3) | 0.92094 (15) | 0.0742 (8) | |
C34A | 0.42095 (14) | 0.5680 (3) | 0.93970 (17) | 0.0836 (9) | |
O34A | 0.40838 (10) | 0.6715 (2) | 0.94747 (16) | 0.1105 (9) | |
H34A | 0.4398 | 0.7065 | 0.9437 | 0.133* | |
C35A | 0.37595 (15) | 0.4921 (3) | 0.94824 (19) | 0.0963 (11) | |
H35A | 0.3369 | 0.5140 | 0.9588 | 0.116* | |
C36A | 0.38717 (17) | 0.3866 (3) | 0.94161 (19) | 0.0958 (11) | |
H36A | 0.3563 | 0.3378 | 0.9489 | 0.115* | |
C37A | 0.44467 (16) | 0.3507 (3) | 0.92390 (17) | 0.0861 (10) | |
C38A | 0.48894 (15) | 0.4273 (3) | 0.91427 (17) | 0.0816 (9) | |
H38A | 0.5276 | 0.4053 | 0.9027 | 0.098* | |
C371 | 0.45684 (19) | 0.2332 (3) | 0.9171 (2) | 0.1145 (14) | |
H37G | 0.4904 | 0.2228 | 0.8902 | 0.172* | |
H37H | 0.4205 | 0.1991 | 0.8988 | 0.172* | |
H37I | 0.4674 | 0.2032 | 0.9578 | 0.172* | |
C1B | 0.01774 (13) | 0.3366 (2) | 0.94131 (15) | 0.0705 (8) | |
C2B | 0.06273 (13) | 0.2592 (2) | 0.94499 (15) | 0.0723 (8) | |
H2B | 0.0511 | 0.1884 | 0.9481 | 0.087* | |
C3B | 0.12532 (13) | 0.2845 (2) | 0.94423 (15) | 0.0705 (8) | |
C4B | 0.14329 (14) | 0.3908 (3) | 0.94466 (16) | 0.0768 (9) | |
C41B | 0.21116 (14) | 0.4211 (3) | 0.9490 (2) | 0.0971 (11) | |
H41D | 0.2306 | 0.3942 | 0.9128 | 0.146* | |
H41E | 0.2308 | 0.3912 | 0.9866 | 0.146* | |
H41F | 0.2150 | 0.4970 | 0.9503 | 0.146* | |
C5B | 0.09770 (15) | 0.4680 (3) | 0.94041 (17) | 0.0846 (10) | |
H5B | 0.1091 | 0.5391 | 0.9387 | 0.101* | |
C6B | 0.03567 (15) | 0.4418 (3) | 0.93866 (17) | 0.0823 (9) | |
H6B | 0.0060 | 0.4951 | 0.9357 | 0.099* | |
N11B | −0.04442 (11) | 0.2985 (2) | 0.94190 (13) | 0.0778 (7) | |
C12B | −0.09087 (14) | 0.3595 (3) | 0.92958 (15) | 0.0771 (9) | |
H12B | −0.0844 | 0.4309 | 0.9210 | 0.092* | |
C13B | −0.15361 (13) | 0.3187 (3) | 0.92884 (15) | 0.0723 (8) | |
C14B | −0.16571 (15) | 0.2126 (3) | 0.93894 (18) | 0.0848 (10) | |
O14B | −0.12015 (11) | 0.14134 (18) | 0.95226 (16) | 0.1075 (9) | |
H14B | −0.0868 | 0.1722 | 0.9555 | 0.129* | |
C15B | −0.22668 (16) | 0.1778 (3) | 0.9357 (2) | 0.1025 (12) | |
H15B | −0.2355 | 0.1067 | 0.9428 | 0.123* | |
C16B | −0.27374 (16) | 0.2483 (4) | 0.9218 (2) | 0.1041 (12) | |
H16B | −0.3141 | 0.2232 | 0.9194 | 0.125* | |
C17B | −0.26363 (15) | 0.3553 (3) | 0.91139 (17) | 0.0867 (10) | |
C172 | −0.31601 (17) | 0.4314 (4) | 0.8967 (2) | 0.1204 (14) | |
H17D | −0.3049 | 0.5005 | 0.9126 | 0.181* | |
H17E | −0.3522 | 0.4071 | 0.9162 | 0.181* | |
H17F | −0.3243 | 0.4352 | 0.8518 | 0.181* | |
C18B | −0.20304 (14) | 0.3885 (3) | 0.91581 (16) | 0.0817 (9) | |
H18B | −0.1946 | 0.4600 | 0.9099 | 0.098* | |
N31B | 0.17307 (11) | 0.2076 (2) | 0.94512 (13) | 0.0732 (7) | |
C32B | 0.16270 (14) | 0.1109 (3) | 0.92933 (16) | 0.0767 (9) | |
H32B | 0.1224 | 0.0900 | 0.9182 | 0.092* | |
C33B | 0.21201 (13) | 0.0327 (3) | 0.92823 (15) | 0.0731 (8) | |
C34B | 0.27389 (14) | 0.0624 (3) | 0.94116 (17) | 0.0808 (9) | |
O34B | 0.28981 (10) | 0.1635 (2) | 0.95421 (14) | 0.1018 (8) | |
H34B | 0.2589 | 0.2010 | 0.9514 | 0.122* | |
C35B | 0.31998 (15) | −0.0138 (3) | 0.94014 (19) | 0.0949 (11) | |
H35B | 0.3611 | 0.0051 | 0.9486 | 0.114* | |
C36B | 0.30446 (18) | −0.1176 (3) | 0.92647 (19) | 0.0998 (12) | |
H36B | 0.3357 | −0.1682 | 0.9265 | 0.120* | |
C37B | 0.24442 (17) | −0.1490 (3) | 0.91276 (19) | 0.0938 (11) | |
C372 | 0.2286 (2) | −0.2651 (3) | 0.9000 (2) | 0.1327 (17) | |
H37A | 0.2587 | −0.3095 | 0.9220 | 0.199* | |
H37B | 0.2286 | −0.2787 | 0.8555 | 0.199* | |
H37C | 0.1884 | −0.2802 | 0.9145 | 0.199* | |
C38B | 0.19921 (15) | −0.0729 (3) | 0.91475 (18) | 0.0888 (10) | |
H38B | 0.1583 | −0.0931 | 0.9067 | 0.107* | |
C1C | 0.16968 (13) | 0.3346 (2) | 0.78195 (15) | 0.0688 (8) | |
C2C | 0.21562 (13) | 0.2585 (2) | 0.77937 (15) | 0.0723 (8) | |
H2C | 0.2049 | 0.1870 | 0.7797 | 0.087* | |
C3C | 0.27801 (13) | 0.2870 (2) | 0.77620 (15) | 0.0705 (8) | |
C4C | 0.29430 (14) | 0.3944 (2) | 0.77632 (15) | 0.0739 (8) | |
C41C | 0.36081 (14) | 0.4291 (3) | 0.77353 (19) | 0.0911 (10) | |
H41G | 0.3768 | 0.4041 | 0.7350 | 0.137* | |
H41H | 0.3848 | 0.4000 | 0.8089 | 0.137* | |
H41I | 0.3630 | 0.5052 | 0.7749 | 0.137* | |
C5C | 0.24782 (15) | 0.4684 (3) | 0.77914 (18) | 0.0873 (10) | |
H5C | 0.2582 | 0.5400 | 0.7791 | 0.105* | |
C6C | 0.18602 (15) | 0.4406 (3) | 0.78212 (18) | 0.0854 (10) | |
H6C | 0.1559 | 0.4929 | 0.7842 | 0.102* | |
N11C | 0.10896 (11) | 0.29445 (19) | 0.78432 (12) | 0.0723 (7) | |
C12C | 0.06132 (14) | 0.3530 (2) | 0.77285 (15) | 0.0734 (8) | |
H12C | 0.0667 | 0.4239 | 0.7623 | 0.088* | |
C13C | −0.00073 (13) | 0.3114 (2) | 0.77598 (15) | 0.0712 (8) | |
C14C | −0.01131 (14) | 0.2049 (3) | 0.79059 (16) | 0.0784 (9) | |
O14C | 0.03577 (10) | 0.13595 (16) | 0.80272 (13) | 0.0927 (7) | |
H14C | 0.0686 | 0.1685 | 0.8052 | 0.111* | |
C15C | −0.07157 (16) | 0.1690 (3) | 0.79355 (18) | 0.0922 (11) | |
H15C | −0.0790 | 0.0987 | 0.8042 | 0.111* | |
C16C | −0.12024 (16) | 0.2368 (3) | 0.78082 (18) | 0.0930 (11) | |
H16C | −0.1602 | 0.2107 | 0.7823 | 0.112* | |
C17C | −0.11207 (14) | 0.3427 (3) | 0.76578 (17) | 0.0864 (10) | |
C173 | −0.16590 (16) | 0.4166 (3) | 0.7530 (2) | 0.1146 (14) | |
H17G | −0.1624 | 0.4756 | 0.7816 | 0.172* | |
H17H | −0.2037 | 0.3792 | 0.7590 | 0.172* | |
H17I | −0.1660 | 0.4419 | 0.7104 | 0.172* | |
C18C | −0.05169 (14) | 0.3784 (3) | 0.76380 (16) | 0.0789 (9) | |
H18C | −0.0448 | 0.4492 | 0.7540 | 0.095* | |
N31C | 0.32559 (11) | 0.2119 (2) | 0.77069 (13) | 0.0730 (7) | |
C32C | 0.31837 (13) | 0.1129 (3) | 0.77830 (16) | 0.0779 (9) | |
H32C | 0.2803 | 0.0886 | 0.7903 | 0.094* | |
C33C | 0.36665 (13) | 0.0360 (3) | 0.76912 (16) | 0.0728 (8) | |
C34C | 0.42593 (14) | 0.0684 (3) | 0.75296 (17) | 0.0800 (9) | |
O34C | 0.43966 (10) | 0.17226 (19) | 0.74604 (15) | 0.1026 (8) | |
H34C | 0.4080 | 0.2076 | 0.7467 | 0.123* | |
C35C | 0.47023 (15) | −0.0075 (3) | 0.74332 (19) | 0.0974 (12) | |
H35C | 0.5094 | 0.0133 | 0.7327 | 0.117* | |
C36C | 0.45710 (17) | −0.1128 (3) | 0.74920 (19) | 0.0984 (11) | |
H36C | 0.4879 | −0.1622 | 0.7427 | 0.118* | |
C37C | 0.39929 (17) | −0.1490 (3) | 0.76456 (19) | 0.0919 (10) | |
C373 | 0.3859 (2) | −0.2664 (3) | 0.7701 (3) | 0.1325 (17) | |
H37D | 0.3456 | −0.2761 | 0.7857 | 0.199* | |
H37E | 0.4163 | −0.2986 | 0.7987 | 0.199* | |
H37F | 0.3872 | −0.2991 | 0.7294 | 0.199* | |
C38C | 0.35585 (15) | −0.0723 (3) | 0.77453 (18) | 0.0866 (10) | |
H38C | 0.3170 | −0.0941 | 0.7855 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1A | 0.0600 (17) | 0.077 (2) | 0.096 (2) | −0.0061 (17) | 0.0048 (15) | −0.0024 (18) |
C2A | 0.0642 (19) | 0.071 (2) | 0.106 (3) | −0.0008 (17) | 0.0088 (16) | −0.0058 (18) |
C3A | 0.0620 (18) | 0.072 (2) | 0.094 (2) | −0.0001 (16) | 0.0056 (16) | −0.0045 (17) |
C4A | 0.070 (2) | 0.071 (2) | 0.105 (3) | 0.0015 (17) | 0.0046 (17) | −0.0081 (18) |
C41A | 0.075 (2) | 0.087 (2) | 0.131 (3) | 0.0139 (19) | 0.007 (2) | −0.006 (2) |
C5A | 0.076 (2) | 0.071 (2) | 0.135 (3) | −0.0001 (19) | −0.002 (2) | −0.005 (2) |
C6A | 0.072 (2) | 0.076 (2) | 0.123 (3) | −0.0079 (18) | −0.0002 (19) | 0.003 (2) |
N11A | 0.0683 (16) | 0.0826 (19) | 0.098 (2) | −0.0037 (14) | 0.0098 (14) | −0.0009 (15) |
C12A | 0.0677 (19) | 0.079 (2) | 0.101 (3) | −0.0037 (18) | 0.0082 (17) | −0.0038 (19) |
C13A | 0.0631 (18) | 0.073 (2) | 0.088 (2) | 0.0020 (16) | 0.0065 (15) | 0.0041 (17) |
C14A | 0.074 (2) | 0.072 (2) | 0.102 (3) | −0.0041 (18) | 0.0157 (17) | 0.0152 (19) |
O14A | 0.0888 (16) | 0.0729 (15) | 0.147 (2) | −0.0037 (13) | 0.0197 (17) | 0.0010 (15) |
C15A | 0.086 (2) | 0.080 (2) | 0.127 (3) | 0.011 (2) | 0.020 (2) | 0.013 (2) |
C16A | 0.074 (2) | 0.113 (3) | 0.111 (3) | 0.013 (2) | 0.019 (2) | 0.027 (3) |
C17A | 0.068 (2) | 0.108 (3) | 0.096 (3) | −0.005 (2) | 0.0101 (17) | 0.019 (2) |
C171 | 0.075 (2) | 0.148 (4) | 0.133 (4) | −0.019 (2) | 0.008 (2) | 0.014 (3) |
C18A | 0.070 (2) | 0.087 (2) | 0.098 (3) | −0.0064 (18) | 0.0116 (17) | 0.0058 (19) |
N31A | 0.0608 (15) | 0.0701 (18) | 0.108 (2) | −0.0010 (13) | 0.0123 (13) | 0.0005 (15) |
C32A | 0.0569 (17) | 0.079 (2) | 0.101 (2) | 0.0003 (17) | 0.0101 (16) | −0.0015 (19) |
C33A | 0.0543 (17) | 0.077 (2) | 0.092 (2) | 0.0006 (16) | 0.0065 (15) | 0.0025 (18) |
C34A | 0.0630 (19) | 0.081 (2) | 0.107 (3) | 0.0035 (18) | 0.0083 (17) | 0.002 (2) |
O34A | 0.0701 (14) | 0.0900 (18) | 0.174 (3) | 0.0110 (13) | 0.0266 (16) | 0.0032 (18) |
C35A | 0.0631 (19) | 0.104 (3) | 0.123 (3) | −0.005 (2) | 0.0171 (19) | 0.006 (2) |
C36A | 0.081 (2) | 0.094 (3) | 0.113 (3) | −0.015 (2) | 0.011 (2) | 0.008 (2) |
C37A | 0.086 (2) | 0.076 (2) | 0.096 (3) | −0.010 (2) | 0.0028 (18) | 0.0026 (19) |
C38A | 0.0669 (19) | 0.076 (2) | 0.103 (3) | 0.0026 (18) | 0.0089 (17) | 0.0020 (19) |
C371 | 0.130 (3) | 0.082 (3) | 0.131 (4) | −0.013 (2) | 0.005 (3) | 0.001 (2) |
C1B | 0.0611 (17) | 0.066 (2) | 0.085 (2) | 0.0011 (16) | 0.0152 (14) | −0.0013 (16) |
C2B | 0.0610 (17) | 0.0634 (19) | 0.094 (2) | −0.0001 (15) | 0.0145 (15) | 0.0029 (16) |
C3B | 0.0610 (17) | 0.069 (2) | 0.083 (2) | −0.0019 (15) | 0.0125 (14) | −0.0038 (16) |
C4B | 0.0666 (18) | 0.072 (2) | 0.093 (2) | −0.0041 (17) | 0.0148 (16) | −0.0087 (17) |
C41B | 0.071 (2) | 0.089 (3) | 0.133 (3) | −0.0129 (19) | 0.015 (2) | −0.011 (2) |
C5B | 0.074 (2) | 0.069 (2) | 0.111 (3) | −0.0043 (18) | 0.0136 (18) | −0.0050 (19) |
C6B | 0.070 (2) | 0.071 (2) | 0.107 (3) | 0.0071 (17) | 0.0161 (17) | −0.0062 (19) |
N11B | 0.0610 (15) | 0.0729 (17) | 0.101 (2) | 0.0075 (13) | 0.0192 (13) | −0.0010 (14) |
C12B | 0.0703 (19) | 0.069 (2) | 0.093 (2) | 0.0025 (17) | 0.0183 (16) | −0.0023 (17) |
C13B | 0.0595 (17) | 0.071 (2) | 0.088 (2) | 0.0038 (15) | 0.0178 (15) | −0.0025 (16) |
C14B | 0.072 (2) | 0.068 (2) | 0.116 (3) | 0.0071 (18) | 0.0188 (18) | 0.0003 (19) |
O14B | 0.0796 (15) | 0.0731 (16) | 0.171 (3) | 0.0071 (13) | 0.0174 (17) | 0.0130 (16) |
C15B | 0.074 (2) | 0.085 (3) | 0.149 (4) | −0.015 (2) | 0.017 (2) | 0.001 (2) |
C16B | 0.062 (2) | 0.121 (3) | 0.130 (3) | −0.003 (2) | 0.011 (2) | −0.005 (3) |
C17B | 0.065 (2) | 0.095 (3) | 0.100 (3) | 0.0114 (19) | 0.0113 (17) | 0.001 (2) |
C172 | 0.083 (2) | 0.151 (4) | 0.128 (4) | 0.029 (3) | 0.005 (2) | 0.000 (3) |
C18B | 0.073 (2) | 0.075 (2) | 0.098 (3) | 0.0084 (17) | 0.0160 (17) | 0.0018 (18) |
N31B | 0.0579 (14) | 0.0700 (17) | 0.0928 (19) | 0.0018 (13) | 0.0138 (12) | 0.0025 (14) |
C32B | 0.0580 (17) | 0.076 (2) | 0.097 (2) | 0.0052 (16) | 0.0143 (15) | −0.0005 (18) |
C33B | 0.0586 (17) | 0.074 (2) | 0.088 (2) | 0.0008 (16) | 0.0200 (14) | 0.0006 (17) |
C34B | 0.0656 (19) | 0.082 (2) | 0.096 (2) | −0.0043 (18) | 0.0169 (16) | 0.0024 (19) |
O34B | 0.0653 (13) | 0.0911 (18) | 0.149 (2) | −0.0026 (13) | 0.0113 (14) | −0.0067 (17) |
C35B | 0.0585 (19) | 0.100 (3) | 0.127 (3) | 0.017 (2) | 0.0135 (18) | 0.003 (2) |
C36B | 0.085 (3) | 0.098 (3) | 0.118 (3) | 0.029 (2) | 0.022 (2) | 0.003 (2) |
C37B | 0.089 (2) | 0.073 (2) | 0.121 (3) | 0.015 (2) | 0.020 (2) | 0.001 (2) |
C372 | 0.138 (4) | 0.090 (3) | 0.173 (5) | 0.022 (3) | 0.027 (3) | −0.019 (3) |
C38B | 0.070 (2) | 0.077 (2) | 0.121 (3) | 0.0000 (19) | 0.0162 (19) | −0.003 (2) |
C1C | 0.0608 (16) | 0.0622 (19) | 0.084 (2) | −0.0015 (15) | 0.0121 (14) | −0.0006 (16) |
C2C | 0.0617 (17) | 0.0620 (19) | 0.094 (2) | −0.0020 (15) | 0.0148 (15) | −0.0035 (16) |
C3C | 0.0631 (18) | 0.067 (2) | 0.082 (2) | −0.0027 (16) | 0.0130 (15) | −0.0001 (16) |
C4C | 0.0669 (18) | 0.068 (2) | 0.087 (2) | −0.0006 (16) | 0.0077 (15) | 0.0000 (16) |
C41C | 0.070 (2) | 0.084 (2) | 0.119 (3) | −0.0116 (18) | 0.0104 (18) | 0.002 (2) |
C5C | 0.078 (2) | 0.062 (2) | 0.122 (3) | −0.0040 (18) | 0.0070 (19) | −0.0014 (19) |
C6C | 0.074 (2) | 0.065 (2) | 0.118 (3) | 0.0066 (17) | 0.0109 (19) | −0.0053 (19) |
N11C | 0.0623 (14) | 0.0671 (16) | 0.0884 (18) | 0.0028 (13) | 0.0126 (12) | −0.0040 (13) |
C12C | 0.0690 (18) | 0.0634 (19) | 0.089 (2) | 0.0027 (16) | 0.0150 (15) | −0.0016 (16) |
C13C | 0.0648 (18) | 0.066 (2) | 0.084 (2) | 0.0035 (15) | 0.0104 (15) | −0.0071 (16) |
C14C | 0.0687 (19) | 0.074 (2) | 0.094 (2) | 0.0026 (17) | 0.0119 (16) | −0.0106 (18) |
O14C | 0.0784 (14) | 0.0636 (14) | 0.137 (2) | 0.0036 (12) | 0.0147 (15) | −0.0009 (14) |
C15C | 0.081 (2) | 0.085 (2) | 0.113 (3) | −0.013 (2) | 0.021 (2) | −0.018 (2) |
C16C | 0.066 (2) | 0.104 (3) | 0.110 (3) | −0.008 (2) | 0.0144 (18) | −0.022 (2) |
C17C | 0.066 (2) | 0.105 (3) | 0.089 (2) | 0.010 (2) | 0.0106 (16) | −0.012 (2) |
C173 | 0.073 (2) | 0.148 (4) | 0.122 (3) | 0.027 (2) | 0.003 (2) | −0.012 (3) |
C18C | 0.0688 (19) | 0.079 (2) | 0.090 (2) | 0.0084 (17) | 0.0129 (16) | −0.0031 (18) |
N31C | 0.0581 (14) | 0.0669 (17) | 0.0951 (19) | 0.0035 (13) | 0.0129 (12) | −0.0012 (14) |
C32C | 0.0532 (17) | 0.079 (2) | 0.103 (3) | −0.0008 (16) | 0.0171 (15) | 0.0027 (19) |
C33C | 0.0567 (17) | 0.072 (2) | 0.091 (2) | 0.0024 (15) | 0.0148 (15) | −0.0005 (17) |
C34C | 0.0648 (19) | 0.074 (2) | 0.103 (3) | 0.0027 (17) | 0.0198 (17) | 0.0008 (19) |
O34C | 0.0680 (13) | 0.0825 (17) | 0.161 (3) | −0.0021 (12) | 0.0334 (15) | 0.0075 (16) |
C35C | 0.063 (2) | 0.102 (3) | 0.130 (3) | 0.011 (2) | 0.0280 (19) | 0.005 (2) |
C36C | 0.083 (2) | 0.098 (3) | 0.116 (3) | 0.027 (2) | 0.019 (2) | −0.001 (2) |
C37C | 0.085 (2) | 0.073 (2) | 0.117 (3) | 0.012 (2) | 0.008 (2) | 0.001 (2) |
C373 | 0.127 (4) | 0.083 (3) | 0.188 (5) | 0.007 (3) | 0.017 (3) | 0.005 (3) |
C38C | 0.0645 (19) | 0.078 (2) | 0.118 (3) | 0.0011 (18) | 0.0124 (18) | 0.005 (2) |
Geometric parameters (Å, º) top
C1A—C2A | 1.376 (4) | C16B—H16B | 0.9300 |
C1A—C6A | 1.394 (4) | C17B—C18B | 1.377 (4) |
C1A—N11A | 1.416 (4) | C17B—C172 | 1.505 (5) |
C2A—C3A | 1.398 (4) | C172—H17D | 0.9600 |
C2A—H2A | 0.9300 | C172—H17E | 0.9600 |
C3A—C4A | 1.392 (4) | C172—H17F | 0.9600 |
C3A—N31A | 1.421 (4) | C18B—H18B | 0.9300 |
C4A—C5A | 1.391 (4) | N31B—C32B | 1.280 (4) |
C4A—C41A | 1.511 (4) | C32B—C33B | 1.456 (4) |
C41A—H41A | 0.9600 | C32B—H32B | 0.9300 |
C41A—H41B | 0.9600 | C33B—C38B | 1.385 (4) |
C41A—H41C | 0.9600 | C33B—C34B | 1.405 (4) |
C5A—C6A | 1.380 (5) | C34B—O34B | 1.344 (4) |
C5A—H5A | 0.9300 | C34B—C35B | 1.387 (4) |
C6A—H6A | 0.9300 | O34B—H34B | 0.8200 |
N11A—C12A | 1.300 (4) | C35B—C36B | 1.377 (5) |
C12A—C13A | 1.450 (4) | C35B—H35B | 0.9300 |
C12A—H12A | 0.9300 | C36B—C37B | 1.376 (5) |
C13A—C18A | 1.385 (4) | C36B—H36B | 0.9300 |
C13A—C14A | 1.399 (4) | C37B—C38B | 1.374 (4) |
C14A—O14A | 1.358 (4) | C37B—C372 | 1.523 (5) |
C14A—C15A | 1.401 (4) | C372—H37A | 0.9600 |
O14A—H14A | 0.8200 | C372—H37B | 0.9600 |
C15A—C16A | 1.387 (5) | C372—H37C | 0.9600 |
C15A—H15A | 0.9300 | C38B—H38B | 0.9300 |
C16A—C17A | 1.380 (5) | C1C—C6C | 1.383 (4) |
C16A—H16A | 0.9300 | C1C—C2C | 1.386 (4) |
C17A—C18A | 1.385 (4) | C1C—N11C | 1.415 (3) |
C17A—C171 | 1.506 (5) | C2C—C3C | 1.406 (4) |
C171—H17A | 0.9600 | C2C—H2C | 0.9300 |
C171—H17B | 0.9600 | C3C—C4C | 1.399 (4) |
C171—H17C | 0.9600 | C3C—N31C | 1.410 (4) |
C18A—H18A | 0.9300 | C4C—C5C | 1.377 (4) |
N31A—C32A | 1.274 (4) | C4C—C41C | 1.512 (4) |
C32A—C33A | 1.451 (4) | C41C—H41G | 0.9600 |
C32A—H32A | 0.9300 | C41C—H41H | 0.9600 |
C33A—C38A | 1.386 (4) | C41C—H41I | 0.9600 |
C33A—C34A | 1.397 (4) | C5C—C6C | 1.391 (4) |
C34A—O34A | 1.344 (4) | C5C—H5C | 0.9300 |
C34A—C35A | 1.386 (4) | C6C—H6C | 0.9300 |
O34A—H34A | 0.8200 | N11C—C12C | 1.281 (3) |
C35A—C36A | 1.360 (5) | C12C—C13C | 1.450 (4) |
C35A—H35A | 0.9300 | C12C—H12C | 0.9300 |
C36A—C37A | 1.399 (5) | C13C—C14C | 1.399 (4) |
C36A—H36A | 0.9300 | C13C—C18C | 1.403 (4) |
C37A—C38A | 1.386 (4) | C14C—O14C | 1.354 (3) |
C37A—C371 | 1.511 (5) | C14C—C15C | 1.388 (4) |
C38A—H38A | 0.9300 | O14C—H14C | 0.8200 |
C371—H37G | 0.9600 | C15C—C16C | 1.373 (5) |
C371—H37H | 0.9600 | C15C—H15C | 0.9300 |
C371—H37I | 0.9600 | C16C—C17C | 1.386 (5) |
C1B—C2B | 1.379 (4) | C16C—H16C | 0.9300 |
C1B—C6B | 1.384 (4) | C17C—C18C | 1.388 (4) |
C1B—N11B | 1.432 (3) | C17C—C173 | 1.505 (4) |
C2B—C3B | 1.396 (4) | C173—H17G | 0.9600 |
C2B—H2B | 0.9300 | C173—H17H | 0.9600 |
C3B—C4B | 1.395 (4) | C173—H17I | 0.9600 |
C3B—N31B | 1.418 (4) | C18C—H18C | 0.9300 |
C4B—C5B | 1.386 (4) | N31C—C32C | 1.269 (4) |
C4B—C41B | 1.518 (4) | C32C—C33C | 1.448 (4) |
C41B—H41D | 0.9600 | C32C—H32C | 0.9300 |
C41B—H41E | 0.9600 | C33C—C38C | 1.390 (4) |
C41B—H41F | 0.9600 | C33C—C34C | 1.411 (4) |
C5B—C6B | 1.384 (4) | C34C—O34C | 1.351 (4) |
C5B—H5B | 0.9300 | C34C—C35C | 1.380 (4) |
C6B—H6B | 0.9300 | O34C—H34C | 0.8200 |
N11B—C12B | 1.282 (4) | C35C—C36C | 1.364 (5) |
C12B—C13B | 1.454 (4) | C35C—H35C | 0.9300 |
C12B—H12B | 0.9300 | C36C—C37C | 1.391 (5) |
C13B—C14B | 1.382 (4) | C36C—H36C | 0.9300 |
C13B—C18B | 1.401 (4) | C37C—C38C | 1.375 (4) |
C14B—O14B | 1.353 (4) | C37C—C373 | 1.514 (5) |
C14B—C15B | 1.391 (4) | C373—H37D | 0.9600 |
O14B—H14B | 0.8200 | C373—H37E | 0.9600 |
C15B—C16B | 1.372 (5) | C373—H37F | 0.9600 |
C15B—H15B | 0.9300 | C38C—H38C | 0.9300 |
C16B—C17B | 1.386 (5) | | |
| | | |
C2A—C1A—C6A | 118.2 (3) | C18B—C17B—C16B | 116.3 (3) |
C2A—C1A—N11A | 116.8 (3) | C18B—C17B—C172 | 121.8 (4) |
C6A—C1A—N11A | 125.0 (3) | C16B—C17B—C172 | 121.9 (3) |
C1A—C2A—C3A | 121.7 (3) | C17B—C172—H17D | 109.5 |
C1A—C2A—H2A | 119.1 | C17B—C172—H17E | 109.5 |
C3A—C2A—H2A | 119.1 | H17D—C172—H17E | 109.5 |
C4A—C3A—C2A | 119.9 (3) | C17B—C172—H17F | 109.5 |
C4A—C3A—N31A | 116.9 (3) | H17D—C172—H17F | 109.5 |
C2A—C3A—N31A | 123.1 (3) | H17E—C172—H17F | 109.5 |
C5A—C4A—C3A | 118.1 (3) | C17B—C18B—C13B | 122.6 (3) |
C5A—C4A—C41A | 120.3 (3) | C17B—C18B—H18B | 118.7 |
C3A—C4A—C41A | 121.7 (3) | C13B—C18B—H18B | 118.7 |
C4A—C41A—H41A | 109.5 | C32B—N31B—C3B | 122.0 (3) |
C4A—C41A—H41B | 109.5 | N31B—C32B—C33B | 122.1 (3) |
H41A—C41A—H41B | 109.5 | N31B—C32B—H32B | 119.0 |
C4A—C41A—H41C | 109.5 | C33B—C32B—H32B | 119.0 |
H41A—C41A—H41C | 109.5 | C38B—C33B—C34B | 118.3 (3) |
H41B—C41A—H41C | 109.5 | C38B—C33B—C32B | 121.0 (3) |
C6A—C5A—C4A | 121.6 (3) | C34B—C33B—C32B | 120.7 (3) |
C6A—C5A—H5A | 119.2 | O34B—C34B—C35B | 118.8 (3) |
C4A—C5A—H5A | 119.2 | O34B—C34B—C33B | 121.6 (3) |
C5A—C6A—C1A | 120.4 (3) | C35B—C34B—C33B | 119.6 (3) |
C5A—C6A—H6A | 119.8 | C34B—O34B—H34B | 109.5 |
C1A—C6A—H6A | 119.8 | C36B—C35B—C34B | 119.5 (3) |
C12A—N11A—C1A | 121.4 (3) | C36B—C35B—H35B | 120.2 |
N11A—C12A—C13A | 121.7 (3) | C34B—C35B—H35B | 120.2 |
N11A—C12A—H12A | 119.1 | C37B—C36B—C35B | 122.3 (3) |
C13A—C12A—H12A | 119.1 | C37B—C36B—H36B | 118.8 |
C18A—C13A—C14A | 119.2 (3) | C35B—C36B—H36B | 118.8 |
C18A—C13A—C12A | 119.7 (3) | C38B—C37B—C36B | 117.4 (3) |
C14A—C13A—C12A | 121.0 (3) | C38B—C37B—C372 | 121.4 (4) |
O14A—C14A—C13A | 122.5 (3) | C36B—C37B—C372 | 121.0 (3) |
O14A—C14A—C15A | 118.0 (3) | C37B—C372—H37A | 109.5 |
C13A—C14A—C15A | 119.6 (3) | C37B—C372—H37B | 109.5 |
C14A—O14A—H14A | 109.5 | H37A—C372—H37B | 109.5 |
C16A—C15A—C14A | 118.9 (4) | C37B—C372—H37C | 109.5 |
C16A—C15A—H15A | 120.5 | H37A—C372—H37C | 109.5 |
C14A—C15A—H15A | 120.5 | H37B—C372—H37C | 109.5 |
C17A—C16A—C15A | 122.5 (3) | C37B—C38B—C33B | 122.8 (3) |
C17A—C16A—H16A | 118.7 | C37B—C38B—H38B | 118.6 |
C15A—C16A—H16A | 118.7 | C33B—C38B—H38B | 118.6 |
C16A—C17A—C18A | 117.5 (3) | C6C—C1C—C2C | 118.9 (3) |
C16A—C17A—C171 | 121.5 (4) | C6C—C1C—N11C | 125.8 (3) |
C18A—C17A—C171 | 121.0 (4) | C2C—C1C—N11C | 115.3 (3) |
C17A—C171—H17A | 109.5 | C1C—C2C—C3C | 121.5 (3) |
C17A—C171—H17B | 109.5 | C1C—C2C—H2C | 119.3 |
H17A—C171—H17B | 109.5 | C3C—C2C—H2C | 119.3 |
C17A—C171—H17C | 109.5 | C4C—C3C—C2C | 119.4 (3) |
H17A—C171—H17C | 109.5 | C4C—C3C—N31C | 117.6 (3) |
H17B—C171—H17C | 109.5 | C2C—C3C—N31C | 123.0 (3) |
C13A—C18A—C17A | 122.3 (3) | C5C—C4C—C3C | 118.0 (3) |
C13A—C18A—H18A | 118.9 | C5C—C4C—C41C | 120.6 (3) |
C17A—C18A—H18A | 118.9 | C3C—C4C—C41C | 121.4 (3) |
C32A—N31A—C3A | 122.9 (3) | C4C—C41C—H41G | 109.5 |
N31A—C32A—C33A | 122.7 (3) | C4C—C41C—H41H | 109.5 |
N31A—C32A—H32A | 118.6 | H41G—C41C—H41H | 109.5 |
C33A—C32A—H32A | 118.6 | C4C—C41C—H41I | 109.5 |
C38A—C33A—C34A | 118.2 (3) | H41G—C41C—H41I | 109.5 |
C38A—C33A—C32A | 120.4 (3) | H41H—C41C—H41I | 109.5 |
C34A—C33A—C32A | 121.4 (3) | C4C—C5C—C6C | 122.8 (3) |
O34A—C34A—C35A | 120.2 (3) | C4C—C5C—H5C | 118.6 |
O34A—C34A—C33A | 120.9 (3) | C6C—C5C—H5C | 118.6 |
C35A—C34A—C33A | 118.8 (3) | C1C—C6C—C5C | 119.4 (3) |
C34A—O34A—H34A | 109.5 | C1C—C6C—H6C | 120.3 |
C36A—C35A—C34A | 121.9 (3) | C5C—C6C—H6C | 120.3 |
C36A—C35A—H35A | 119.0 | C12C—N11C—C1C | 122.0 (3) |
C34A—C35A—H35A | 119.0 | N11C—C12C—C13C | 121.6 (3) |
C35A—C36A—C37A | 120.8 (3) | N11C—C12C—H12C | 119.2 |
C35A—C36A—H36A | 119.6 | C13C—C12C—H12C | 119.2 |
C37A—C36A—H36A | 119.6 | C14C—C13C—C18C | 118.7 (3) |
C38A—C37A—C36A | 116.8 (3) | C14C—C13C—C12C | 121.5 (3) |
C38A—C37A—C371 | 122.8 (3) | C18C—C13C—C12C | 119.8 (3) |
C36A—C37A—C371 | 120.4 (3) | O14C—C14C—C15C | 118.9 (3) |
C37A—C38A—C33A | 123.4 (3) | O14C—C14C—C13C | 121.7 (3) |
C37A—C38A—H38A | 118.3 | C15C—C14C—C13C | 119.3 (3) |
C33A—C38A—H38A | 118.3 | C14C—O14C—H14C | 109.5 |
C37A—C371—H37G | 109.5 | C16C—C15C—C14C | 120.2 (4) |
C37A—C371—H37H | 109.5 | C16C—C15C—H15C | 119.9 |
H37G—C371—H37H | 109.5 | C14C—C15C—H15C | 119.9 |
C37A—C371—H37I | 109.5 | C15C—C16C—C17C | 122.5 (3) |
H37G—C371—H37I | 109.5 | C15C—C16C—H16C | 118.7 |
H37H—C371—H37I | 109.5 | C17C—C16C—H16C | 118.7 |
C2B—C1B—C6B | 118.7 (3) | C16C—C17C—C18C | 116.9 (3) |
C2B—C1B—N11B | 115.3 (3) | C16C—C17C—C173 | 121.9 (3) |
C6B—C1B—N11B | 126.0 (3) | C18C—C17C—C173 | 121.2 (4) |
C1B—C2B—C3B | 121.6 (3) | C17C—C173—H17G | 109.5 |
C1B—C2B—H2B | 119.2 | C17C—C173—H17H | 109.5 |
C3B—C2B—H2B | 119.2 | H17G—C173—H17H | 109.5 |
C4B—C3B—C2B | 119.4 (3) | C17C—C173—H17I | 109.5 |
C4B—C3B—N31B | 116.9 (3) | H17G—C173—H17I | 109.5 |
C2B—C3B—N31B | 123.6 (3) | H17H—C173—H17I | 109.5 |
C5B—C4B—C3B | 118.4 (3) | C17C—C18C—C13C | 122.3 (3) |
C5B—C4B—C41B | 120.9 (3) | C17C—C18C—H18C | 118.8 |
C3B—C4B—C41B | 120.7 (3) | C13C—C18C—H18C | 118.8 |
C4B—C41B—H41D | 109.5 | C32C—N31C—C3C | 123.5 (3) |
C4B—C41B—H41E | 109.5 | N31C—C32C—C33C | 123.0 (3) |
H41D—C41B—H41E | 109.5 | N31C—C32C—H32C | 118.5 |
C4B—C41B—H41F | 109.5 | C33C—C32C—H32C | 118.5 |
H41D—C41B—H41F | 109.5 | C38C—C33C—C34C | 117.7 (3) |
H41E—C41B—H41F | 109.5 | C38C—C33C—C32C | 121.2 (3) |
C6B—C5B—C4B | 121.5 (3) | C34C—C33C—C32C | 121.1 (3) |
C6B—C5B—H5B | 119.2 | O34C—C34C—C35C | 119.7 (3) |
C4B—C5B—H5B | 119.2 | O34C—C34C—C33C | 121.1 (3) |
C1B—C6B—C5B | 120.2 (3) | C35C—C34C—C33C | 119.2 (3) |
C1B—C6B—H6B | 119.9 | C34C—O34C—H34C | 109.5 |
C5B—C6B—H6B | 119.9 | C36C—C35C—C34C | 120.6 (3) |
C12B—N11B—C1B | 121.8 (3) | C36C—C35C—H35C | 119.7 |
N11B—C12B—C13B | 120.9 (3) | C34C—C35C—H35C | 119.7 |
N11B—C12B—H12B | 119.5 | C35C—C36C—C37C | 122.4 (3) |
C13B—C12B—H12B | 119.5 | C35C—C36C—H36C | 118.8 |
C14B—C13B—C18B | 119.2 (3) | C37C—C36C—H36C | 118.8 |
C14B—C13B—C12B | 121.8 (3) | C38C—C37C—C36C | 116.2 (3) |
C18B—C13B—C12B | 119.0 (3) | C38C—C37C—C373 | 122.6 (4) |
O14B—C14B—C13B | 122.1 (3) | C36C—C37C—C373 | 121.2 (3) |
O14B—C14B—C15B | 118.8 (3) | C37C—C373—H37D | 109.5 |
C13B—C14B—C15B | 119.1 (3) | C37C—C373—H37E | 109.5 |
C14B—O14B—H14B | 109.5 | H37D—C373—H37E | 109.5 |
C16B—C15B—C14B | 120.0 (4) | C37C—C373—H37F | 109.5 |
C16B—C15B—H15B | 120.0 | H37D—C373—H37F | 109.5 |
C14B—C15B—H15B | 120.0 | H37E—C373—H37F | 109.5 |
C15B—C16B—C17B | 122.8 (3) | C37C—C38C—C33C | 123.8 (3) |
C15B—C16B—H16B | 118.6 | C37C—C38C—H38C | 118.1 |
C17B—C16B—H16B | 118.6 | C33C—C38C—H38C | 118.1 |
| | | |
C6A—C1A—C2A—C3A | −1.4 (5) | C15B—C16B—C17B—C18B | −0.2 (6) |
N11A—C1A—C2A—C3A | 179.7 (3) | C15B—C16B—C17B—C172 | −179.6 (4) |
C1A—C2A—C3A—C4A | 0.0 (5) | C16B—C17B—C18B—C13B | 1.2 (5) |
C1A—C2A—C3A—N31A | −179.0 (3) | C172—C17B—C18B—C13B | −179.4 (3) |
C2A—C3A—C4A—C5A | 1.4 (5) | C14B—C13B—C18B—C17B | −1.3 (5) |
N31A—C3A—C4A—C5A | −179.5 (3) | C12B—C13B—C18B—C17B | 177.0 (3) |
C2A—C3A—C4A—C41A | −178.9 (3) | C4B—C3B—N31B—C32B | −162.3 (3) |
N31A—C3A—C4A—C41A | 0.1 (5) | C2B—C3B—N31B—C32B | 19.8 (5) |
C3A—C4A—C5A—C6A | −1.4 (6) | C3B—N31B—C32B—C33B | 177.9 (3) |
C41A—C4A—C5A—C6A | 178.9 (3) | N31B—C32B—C33B—C38B | 176.0 (3) |
C4A—C5A—C6A—C1A | 0.0 (6) | N31B—C32B—C33B—C34B | −3.7 (5) |
C2A—C1A—C6A—C5A | 1.4 (5) | C38B—C33B—C34B—O34B | 179.6 (3) |
N11A—C1A—C6A—C5A | −179.8 (3) | C32B—C33B—C34B—O34B | −0.7 (5) |
C2A—C1A—N11A—C12A | −158.5 (3) | C38B—C33B—C34B—C35B | −0.1 (5) |
C6A—C1A—N11A—C12A | 22.6 (5) | C32B—C33B—C34B—C35B | 179.7 (3) |
C1A—N11A—C12A—C13A | −178.8 (3) | O34B—C34B—C35B—C36B | −179.6 (4) |
N11A—C12A—C13A—C18A | −180.0 (3) | C33B—C34B—C35B—C36B | 0.0 (6) |
N11A—C12A—C13A—C14A | −2.1 (5) | C34B—C35B—C36B—C37B | 0.9 (6) |
C18A—C13A—C14A—O14A | 179.8 (3) | C35B—C36B—C37B—C38B | −1.7 (6) |
C12A—C13A—C14A—O14A | 1.9 (5) | C35B—C36B—C37B—C372 | −177.9 (4) |
C18A—C13A—C14A—C15A | −1.4 (5) | C36B—C37B—C38B—C33B | 1.7 (6) |
C12A—C13A—C14A—C15A | −179.3 (3) | C372—C37B—C38B—C33B | 177.9 (4) |
O14A—C14A—C15A—C16A | −179.5 (3) | C34B—C33B—C38B—C37B | −0.8 (5) |
C13A—C14A—C15A—C16A | 1.6 (5) | C32B—C33B—C38B—C37B | 179.5 (3) |
C14A—C15A—C16A—C17A | −1.3 (6) | C6C—C1C—C2C—C3C | −0.7 (5) |
C15A—C16A—C17A—C18A | 0.6 (6) | N11C—C1C—C2C—C3C | 179.4 (3) |
C15A—C16A—C17A—C171 | −179.3 (4) | C1C—C2C—C3C—C4C | 0.7 (5) |
C14A—C13A—C18A—C17A | 0.7 (5) | C1C—C2C—C3C—N31C | −177.1 (3) |
C12A—C13A—C18A—C17A | 178.6 (3) | C2C—C3C—C4C—C5C | −0.4 (5) |
C16A—C17A—C18A—C13A | −0.3 (5) | N31C—C3C—C4C—C5C | 177.5 (3) |
C171—C17A—C18A—C13A | 179.6 (3) | C2C—C3C—C4C—C41C | 179.5 (3) |
C4A—C3A—N31A—C32A | 170.3 (3) | N31C—C3C—C4C—C41C | −2.6 (5) |
C2A—C3A—N31A—C32A | −10.7 (5) | C3C—C4C—C5C—C6C | 0.3 (5) |
C3A—N31A—C32A—C33A | 177.9 (3) | C41C—C4C—C5C—C6C | −179.6 (3) |
N31A—C32A—C33A—C38A | −177.7 (3) | C2C—C1C—C6C—C5C | 0.6 (5) |
N31A—C32A—C33A—C34A | 1.1 (5) | N11C—C1C—C6C—C5C | −179.5 (3) |
C38A—C33A—C34A—O34A | 179.4 (3) | C4C—C5C—C6C—C1C | −0.3 (6) |
C32A—C33A—C34A—O34A | 0.6 (5) | C6C—C1C—N11C—C12C | 15.9 (5) |
C38A—C33A—C34A—C35A | −2.7 (5) | C2C—C1C—N11C—C12C | −164.2 (3) |
C32A—C33A—C34A—C35A | 178.5 (3) | C1C—N11C—C12C—C13C | −179.4 (3) |
O34A—C34A—C35A—C36A | −179.1 (4) | N11C—C12C—C13C—C14C | −1.1 (5) |
C33A—C34A—C35A—C36A | 3.0 (6) | N11C—C12C—C13C—C18C | 179.3 (3) |
C34A—C35A—C36A—C37A | −1.9 (6) | C18C—C13C—C14C—O14C | 179.9 (3) |
C35A—C36A—C37A—C38A | 0.6 (6) | C12C—C13C—C14C—O14C | 0.3 (5) |
C35A—C36A—C37A—C371 | 179.6 (4) | C18C—C13C—C14C—C15C | −0.9 (5) |
C36A—C37A—C38A—C33A | −0.4 (5) | C12C—C13C—C14C—C15C | 179.5 (3) |
C371—C37A—C38A—C33A | −179.4 (3) | O14C—C14C—C15C—C16C | −179.3 (3) |
C34A—C33A—C38A—C37A | 1.5 (5) | C13C—C14C—C15C—C16C | 1.5 (5) |
C32A—C33A—C38A—C37A | −179.7 (3) | C14C—C15C—C16C—C17C | −1.1 (6) |
C6B—C1B—C2B—C3B | −1.9 (5) | C15C—C16C—C17C—C18C | 0.2 (5) |
N11B—C1B—C2B—C3B | 179.3 (3) | C15C—C16C—C17C—C173 | −178.9 (3) |
C1B—C2B—C3B—C4B | 5.0 (5) | C16C—C17C—C18C—C13C | 0.3 (5) |
C1B—C2B—C3B—N31B | −177.1 (3) | C173—C17C—C18C—C13C | 179.5 (3) |
C2B—C3B—C4B—C5B | −5.4 (5) | C14C—C13C—C18C—C17C | 0.0 (5) |
N31B—C3B—C4B—C5B | 176.6 (3) | C12C—C13C—C18C—C17C | 179.6 (3) |
C2B—C3B—C4B—C41B | 175.2 (3) | C4C—C3C—N31C—C32C | 170.4 (3) |
N31B—C3B—C4B—C41B | −2.8 (5) | C2C—C3C—N31C—C32C | −11.8 (5) |
C3B—C4B—C5B—C6B | 2.9 (5) | C3C—N31C—C32C—C33C | 176.5 (3) |
C41B—C4B—C5B—C6B | −177.7 (3) | N31C—C32C—C33C—C38C | −176.4 (3) |
C2B—C1B—C6B—C5B | −0.7 (5) | N31C—C32C—C33C—C34C | 2.2 (5) |
N11B—C1B—C6B—C5B | 177.9 (3) | C38C—C33C—C34C—O34C | 179.1 (3) |
C4B—C5B—C6B—C1B | 0.2 (5) | C32C—C33C—C34C—O34C | 0.5 (5) |
C2B—C1B—N11B—C12B | −169.6 (3) | C38C—C33C—C34C—C35C | 0.0 (5) |
C6B—C1B—N11B—C12B | 11.7 (5) | C32C—C33C—C34C—C35C | −178.6 (3) |
C1B—N11B—C12B—C13B | 178.4 (3) | O34C—C34C—C35C—C36C | −179.1 (4) |
N11B—C12B—C13B—C14B | −2.4 (5) | C33C—C34C—C35C—C36C | 0.1 (6) |
N11B—C12B—C13B—C18B | 179.3 (3) | C34C—C35C—C36C—C37C | 0.4 (7) |
C18B—C13B—C14B—O14B | −179.4 (3) | C35C—C36C—C37C—C38C | −0.9 (6) |
C12B—C13B—C14B—O14B | 2.3 (5) | C35C—C36C—C37C—C373 | 179.4 (4) |
C18B—C13B—C14B—C15B | 0.3 (5) | C36C—C37C—C38C—C33C | 1.0 (6) |
C12B—C13B—C14B—C15B | −178.0 (3) | C373—C37C—C38C—C33C | −179.3 (4) |
O14B—C14B—C15B—C16B | −179.6 (4) | C34C—C33C—C38C—C37C | −0.6 (6) |
C13B—C14B—C15B—C16B | 0.7 (6) | C32C—C33C—C38C—C37C | 178.0 (4) |
C14B—C15B—C16B—C17B | −0.8 (7) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18A—H18A···O14Bi | 0.93 | 2.60 | 3.531 (4) | 175 |
C36A—H36A···O34B | 0.93 | 2.63 | 3.536 (5) | 164 |
C18B—H18B···O14Aii | 0.93 | 2.49 | 3.377 (4) | 160 |
C36B—H36B···O34Aiii | 0.93 | 2.59 | 3.496 (4) | 167 |
C173—H17G···O14Aii | 0.96 | 2.68 | 3.603 (5) | 162 |
C18C—H18C···O14Civ | 0.93 | 2.66 | 3.564 (4) | 165 |
C36C—H36C···O34Cv | 0.93 | 2.61 | 3.512 (4) | 163 |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) x, y−1, z; (iv) −x, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2. |
Crystal data top
C23H22N2O2 | F(000) = 1520 |
Mr = 358.42 | Dx = 1.307 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
a = 9.464 (2) Å | Cell parameters from 3751 reflections |
b = 20.640 (3) Å | θ = 4–55° |
c = 19.219 (3) Å | µ = 0.67 mm−1 |
β = 103.93 (2)° | T = 130 K |
V = 3643.8 (11) Å3 | Prism, red |
Z = 8 | 0.2 × 0.15 × 0.1 mm |
Data collection top
SuperNova, Single source at offset), Atlas diffractometer | 12478 independent reflections |
Radiation source: SuperNova (Cu) X-ray Source | 9327 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.064 |
Detector resolution: 10.5357 pixels mm-1 | θmax = 74.4°, θmin = 2.4° |
ω–scan | h = −11→11 |
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −25→25 |
Tmin = 0.920, Tmax = 1.000 | l = −21→23 |
27193 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.0899P)2 + 0.6139P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.188 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.31 e Å−3 |
12478 reflections | Δρmin = −0.26 e Å−3 |
993 parameters | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
1 restraint | Absolute structure parameter: 0.5 (4) |
Crystal data top
C23H22N2O2 | V = 3643.8 (11) Å3 |
Mr = 358.42 | Z = 8 |
Monoclinic, P21 | Cu Kα radiation |
a = 9.464 (2) Å | µ = 0.67 mm−1 |
b = 20.640 (3) Å | T = 130 K |
c = 19.219 (3) Å | 0.2 × 0.15 × 0.1 mm |
β = 103.93 (2)° | |
Data collection top
SuperNova, Single source at offset), Atlas diffractometer | 12478 independent reflections |
Absorption correction: multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | 9327 reflections with I > 2σ(I) |
Tmin = 0.920, Tmax = 1.000 | Rint = 0.064 |
27193 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.188 | Δρmax = 0.31 e Å−3 |
S = 1.02 | Δρmin = −0.26 e Å−3 |
12478 reflections | Absolute structure: Classical Flack method preferred over Parsons because s.u. lower. |
993 parameters | Absolute structure parameter: 0.5 (4) |
1 restraint | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C37A | 0.7537 (6) | 0.5563 (3) | 0.1790 (3) | 0.0391 (12) | |
C1A | 0.4168 (7) | 0.8896 (3) | 0.0420 (3) | 0.0322 (12) | |
C2A | 0.4955 (6) | 0.8321 (3) | 0.0584 (3) | 0.0304 (11) | |
H2A | 0.4979 | 0.8111 | 0.1026 | 0.037* | |
C3A | 0.5706 (6) | 0.8046 (3) | 0.0117 (3) | 0.0306 (11) | |
C4A | 0.5745 (7) | 0.8362 (3) | −0.0525 (3) | 0.0328 (12) | |
C41A | 0.6556 (7) | 0.8069 (3) | −0.1039 (3) | 0.0356 (12) | |
H41A | 0.6588 | 0.8382 | −0.1418 | 0.053* | |
H41B | 0.6053 | 0.7676 | −0.1253 | 0.053* | |
H41C | 0.7550 | 0.7960 | −0.0779 | 0.053* | |
C5A | 0.4975 (7) | 0.8940 (3) | −0.0676 (3) | 0.0330 (12) | |
H5A | 0.4989 | 0.9158 | −0.1109 | 0.040* | |
C6A | 0.4188 (7) | 0.9213 (3) | −0.0229 (3) | 0.0331 (12) | |
H6A | 0.3671 | 0.9607 | −0.0357 | 0.040* | |
N11A | 0.3415 (6) | 0.9108 (2) | 0.0924 (3) | 0.0326 (10) | |
C12A | 0.2730 (7) | 0.9649 (3) | 0.0856 (3) | 0.0320 (11) | |
H12A | 0.2760 | 0.9923 | 0.0463 | 0.038* | |
C13A | 0.1913 (6) | 0.9851 (3) | 0.1365 (3) | 0.0305 (11) | |
C14A | 0.1809 (7) | 0.9467 (3) | 0.1958 (3) | 0.0326 (12) | |
O14A | 0.2459 (5) | 0.8877 (2) | 0.2076 (2) | 0.0388 (10) | |
H14A | 0.3007 | 0.8824 | 0.1796 | 0.047* | |
C15A | 0.1009 (7) | 0.9686 (3) | 0.2432 (3) | 0.0350 (12) | |
H15A | 0.0923 | 0.9424 | 0.2826 | 0.042* | |
C16A | 0.0345 (7) | 1.0281 (3) | 0.2330 (3) | 0.0374 (13) | |
H16A | −0.0191 | 1.0425 | 0.2660 | 0.045* | |
C17A | 0.0435 (6) | 1.0686 (3) | 0.1750 (3) | 0.0323 (11) | |
C171 | −0.0290 (7) | 1.1335 (3) | 0.1656 (3) | 0.0393 (13) | |
H17A | 0.0145 | 1.1604 | 0.1343 | 0.059* | |
H17B | −0.0158 | 1.1546 | 0.2124 | 0.059* | |
H17C | −0.1332 | 1.1281 | 0.1440 | 0.059* | |
C18A | 0.1212 (6) | 1.0455 (2) | 0.1277 (3) | 0.0323 (12) | |
H18A | 0.1273 | 1.0715 | 0.0877 | 0.039* | |
N31A | 0.6501 (5) | 0.7459 (2) | 0.0283 (2) | 0.0318 (10) | |
C32A | 0.6155 (6) | 0.7045 (2) | 0.0711 (3) | 0.0346 (10) | |
H32A | 0.5307 | 0.7121 | 0.0881 | 0.042* | |
C33A | 0.7001 (6) | 0.6468 (3) | 0.0945 (3) | 0.0354 (11) | |
C34A | 0.8186 (6) | 0.6289 (3) | 0.0655 (3) | 0.0374 (12) | |
O34A | 0.8540 (4) | 0.6636 (2) | 0.0121 (2) | 0.0457 (9) | |
H34A | 0.7947 | 0.6942 | 0.0001 | 0.055* | |
C35A | 0.9005 (6) | 0.5744 (3) | 0.0925 (3) | 0.0426 (12) | |
H35A | 0.9782 | 0.5611 | 0.0724 | 0.051* | |
C36A | 0.8692 (6) | 0.5397 (3) | 0.1485 (3) | 0.0404 (13) | |
H36A | 0.9279 | 0.5034 | 0.1669 | 0.048* | |
C371 | 0.7246 (7) | 0.5186 (3) | 0.2408 (3) | 0.0470 (13) | |
H37A | 0.6353 | 0.5346 | 0.2521 | 0.070* | |
H37B | 0.8065 | 0.5239 | 0.2827 | 0.070* | |
H37C | 0.7131 | 0.4726 | 0.2279 | 0.070* | |
C38A | 0.6712 (6) | 0.6097 (2) | 0.1507 (3) | 0.0362 (11) | |
H38A | 0.5917 | 0.6217 | 0.1701 | 0.043* | |
C1B | −0.0735 (7) | 0.8851 (3) | 0.0477 (3) | 0.0318 (12) | |
C2B | −0.0007 (6) | 0.8264 (3) | 0.0634 (3) | 0.0302 (11) | |
H2B | −0.0080 | 0.8036 | 0.1054 | 0.036* | |
C3B | 0.0826 (6) | 0.7999 (2) | 0.0197 (3) | 0.0303 (11) | |
C4B | 0.0885 (6) | 0.8308 (3) | −0.0448 (3) | 0.0309 (11) | |
C41B | 0.1664 (7) | 0.8012 (3) | −0.0968 (3) | 0.0333 (12) | |
H41D | 0.1708 | 0.8327 | −0.1344 | 0.050* | |
H41E | 0.1137 | 0.7625 | −0.1186 | 0.050* | |
H41F | 0.2654 | 0.7891 | −0.0713 | 0.050* | |
C5B | 0.0137 (7) | 0.8896 (3) | −0.0599 (3) | 0.0320 (12) | |
H5B | 0.0174 | 0.9117 | −0.1028 | 0.038* | |
C6B | −0.0648 (7) | 0.9171 (3) | −0.0159 (3) | 0.0339 (12) | |
H6B | −0.1128 | 0.9573 | −0.0284 | 0.041* | |
N11B | −0.1541 (6) | 0.9060 (2) | 0.0963 (2) | 0.0311 (10) | |
C12B | −0.2146 (6) | 0.9619 (3) | 0.0909 (3) | 0.0304 (11) | |
H12B | −0.2019 | 0.9905 | 0.0542 | 0.036* | |
C13B | −0.3017 (6) | 0.9828 (3) | 0.1392 (3) | 0.0294 (11) | |
C14B | −0.3169 (7) | 0.9455 (2) | 0.1983 (3) | 0.0315 (12) | |
O14B | −0.2492 (5) | 0.8873 (2) | 0.2127 (2) | 0.0385 (10) | |
H14B | −0.1983 | 0.8802 | 0.1832 | 0.046* | |
C15B | −0.4026 (7) | 0.9677 (3) | 0.2427 (3) | 0.0320 (11) | |
H15B | −0.4135 | 0.9422 | 0.2822 | 0.038* | |
C16B | −0.4719 (7) | 1.0271 (3) | 0.2294 (3) | 0.0345 (12) | |
H16B | −0.5289 | 1.0421 | 0.2607 | 0.041* | |
C17B | −0.4602 (6) | 1.0657 (3) | 0.1707 (3) | 0.0297 (10) | |
C172 | −0.5354 (7) | 1.1300 (3) | 0.1579 (3) | 0.0377 (12) | |
H17D | −0.4903 | 1.1564 | 0.1267 | 0.057* | |
H17E | −0.5264 | 1.1523 | 0.2038 | 0.057* | |
H17F | −0.6385 | 1.1234 | 0.1348 | 0.057* | |
C18B | −0.3742 (6) | 1.0429 (2) | 0.1273 (3) | 0.0300 (11) | |
H18B | −0.3636 | 1.0687 | 0.0879 | 0.036* | |
N31B | 0.1581 (6) | 0.7407 (2) | 0.0363 (2) | 0.0319 (10) | |
C32B | 0.1917 (5) | 0.7200 (2) | 0.1013 (3) | 0.0330 (10) | |
H32B | 0.1780 | 0.7479 | 0.1384 | 0.040* | |
C33B | 0.2498 (5) | 0.6554 (2) | 0.1201 (3) | 0.0326 (10) | |
C34B | 0.2835 (6) | 0.6144 (3) | 0.0678 (3) | 0.0351 (12) | |
O34B | 0.2728 (5) | 0.63493 (19) | −0.00018 (19) | 0.0452 (9) | |
H34B | 0.2310 | 0.6711 | −0.0062 | 0.054* | |
C35B | 0.3316 (6) | 0.5514 (3) | 0.0866 (3) | 0.0377 (11) | |
H35B | 0.3589 | 0.5240 | 0.0523 | 0.045* | |
C36B | 0.3393 (6) | 0.5290 (3) | 0.1551 (3) | 0.0361 (12) | |
H36B | 0.3701 | 0.4857 | 0.1668 | 0.043* | |
C37B | 0.3032 (6) | 0.5681 (2) | 0.2080 (3) | 0.0346 (10) | |
C372 | 0.3104 (6) | 0.5407 (3) | 0.2808 (3) | 0.0422 (12) | |
H37D | 0.2978 | 0.5756 | 0.3133 | 0.063* | |
H37E | 0.4052 | 0.5200 | 0.2991 | 0.063* | |
H37F | 0.2329 | 0.5085 | 0.2776 | 0.063* | |
C38B | 0.2625 (5) | 0.6314 (2) | 0.1893 (3) | 0.0326 (10) | |
H38B | 0.2425 | 0.6595 | 0.2249 | 0.039* | |
C1C | 0.8225 (6) | 0.4044 (3) | 0.4525 (3) | 0.0293 (11) | |
C2C | 0.7459 (7) | 0.4626 (3) | 0.4372 (3) | 0.0323 (12) | |
H2C | 0.7443 | 0.4843 | 0.3934 | 0.039* | |
C3C | 0.6717 (6) | 0.4895 (3) | 0.4846 (3) | 0.0319 (12) | |
C4C | 0.6681 (6) | 0.4575 (3) | 0.5486 (3) | 0.0308 (11) | |
C41C | 0.5891 (7) | 0.4847 (3) | 0.6003 (3) | 0.0379 (13) | |
H41G | 0.6102 | 0.4585 | 0.6441 | 0.057* | |
H41H | 0.4842 | 0.4842 | 0.5787 | 0.057* | |
H41I | 0.6211 | 0.5294 | 0.6122 | 0.057* | |
C5C | 0.7424 (7) | 0.3987 (3) | 0.5628 (3) | 0.0338 (12) | |
H5C | 0.7403 | 0.3759 | 0.6055 | 0.041* | |
C6C | 0.8189 (7) | 0.3727 (3) | 0.5165 (3) | 0.0351 (12) | |
H6C | 0.8695 | 0.3329 | 0.5282 | 0.042* | |
N11C | 0.9014 (5) | 0.3842 (2) | 0.4024 (2) | 0.0313 (10) | |
C12C | 0.9602 (6) | 0.3276 (3) | 0.4057 (3) | 0.0323 (12) | |
H12C | 0.9450 | 0.2980 | 0.4410 | 0.039* | |
C13C | 1.0482 (7) | 0.3075 (3) | 0.3578 (3) | 0.0324 (12) | |
C14C | 1.0693 (7) | 0.3474 (3) | 0.3017 (3) | 0.0330 (12) | |
O14C | 1.0048 (5) | 0.4064 (2) | 0.2889 (2) | 0.0410 (10) | |
H14C | 0.9708 | 0.4170 | 0.3238 | 0.049* | |
C15C | 1.1543 (7) | 0.3252 (3) | 0.2574 (3) | 0.0375 (13) | |
H15C | 1.1671 | 0.3514 | 0.2187 | 0.045* | |
C16C | 1.2211 (7) | 0.2650 (3) | 0.2689 (3) | 0.0355 (12) | |
H16C | 1.2796 | 0.2508 | 0.2381 | 0.043* | |
C17C | 1.2043 (7) | 0.2249 (3) | 0.3246 (3) | 0.0360 (12) | |
C173 | 1.2786 (8) | 0.1591 (3) | 0.3383 (4) | 0.0452 (15) | |
H17G | 1.2870 | 0.1463 | 0.3882 | 0.068* | |
H17H | 1.3760 | 0.1618 | 0.3291 | 0.068* | |
H17I | 1.2208 | 0.1268 | 0.3063 | 0.068* | |
N31C | 0.5923 (6) | 0.5483 (2) | 0.4686 (3) | 0.0344 (10) | |
C32C | 0.6270 (6) | 0.5894 (2) | 0.4257 (3) | 0.0358 (11) | |
H32C | 0.7124 | 0.5821 | 0.4090 | 0.043* | |
C33C | 0.5407 (6) | 0.6468 (2) | 0.4018 (3) | 0.0340 (11) | |
C34C | 0.4222 (6) | 0.6639 (3) | 0.4295 (3) | 0.0365 (12) | |
O34C | 0.3850 (5) | 0.62941 (19) | 0.4820 (2) | 0.0447 (9) | |
H34C | 0.4388 | 0.5966 | 0.4915 | 0.054* | |
C35C | 0.3387 (6) | 0.7179 (3) | 0.4018 (3) | 0.0417 (12) | |
H35C | 0.2591 | 0.7306 | 0.4208 | 0.050* | |
C36C | 0.3727 (7) | 0.7534 (3) | 0.3460 (3) | 0.0406 (13) | |
H36C | 0.3139 | 0.7896 | 0.3272 | 0.049* | |
C37C | 0.4888 (6) | 0.7376 (3) | 0.3173 (3) | 0.0388 (11) | |
C373 | 0.5218 (7) | 0.7748 (3) | 0.2554 (3) | 0.0450 (12) | |
H37G | 0.4631 | 0.7575 | 0.2102 | 0.067* | |
H37H | 0.6253 | 0.7703 | 0.2564 | 0.067* | |
H37I | 0.4984 | 0.8207 | 0.2596 | 0.067* | |
C38C | 0.5725 (6) | 0.6841 (2) | 0.3462 (3) | 0.0369 (11) | |
H38C | 0.6537 | 0.6725 | 0.3278 | 0.044* | |
C1D | 0.3339 (6) | 0.3945 (2) | 0.4605 (3) | 0.0286 (11) | |
C2D | 0.2593 (7) | 0.4524 (3) | 0.4441 (3) | 0.0323 (12) | |
H2D | 0.2652 | 0.4750 | 0.4018 | 0.039* | |
C3D | 0.1757 (6) | 0.4785 (3) | 0.4880 (3) | 0.0302 (11) | |
C4D | 0.1731 (6) | 0.4482 (3) | 0.5531 (3) | 0.0306 (11) | |
C41D | 0.0916 (7) | 0.4765 (3) | 0.6037 (3) | 0.0364 (12) | |
H41J | 0.0998 | 0.4475 | 0.6449 | 0.055* | |
H41K | −0.0112 | 0.4815 | 0.5790 | 0.055* | |
H41L | 0.1327 | 0.5189 | 0.6204 | 0.055* | |
C5D | 0.2490 (7) | 0.3901 (3) | 0.5691 (3) | 0.0317 (11) | |
H5D | 0.2464 | 0.3682 | 0.6123 | 0.038* | |
C6D | 0.3283 (7) | 0.3631 (3) | 0.5244 (3) | 0.0335 (12) | |
H6D | 0.3787 | 0.3234 | 0.5371 | 0.040* | |
N11D | 0.4149 (5) | 0.3742 (2) | 0.4111 (2) | 0.0307 (10) | |
C12D | 0.4816 (6) | 0.3193 (3) | 0.4168 (3) | 0.0319 (11) | |
H12D | 0.4775 | 0.2915 | 0.4557 | 0.038* | |
C13D | 0.5626 (6) | 0.2987 (3) | 0.3656 (3) | 0.0307 (11) | |
C14D | 0.5698 (6) | 0.3375 (3) | 0.3059 (3) | 0.0307 (11) | |
O14D | 0.5017 (5) | 0.39576 (19) | 0.2934 (2) | 0.0373 (9) | |
H14D | 0.4752 | 0.4076 | 0.3301 | 0.045* | |
C15D | 0.6463 (7) | 0.3151 (3) | 0.2580 (3) | 0.0369 (13) | |
H15D | 0.6520 | 0.3411 | 0.2180 | 0.044* | |
C16D | 0.7149 (7) | 0.2553 (3) | 0.2675 (3) | 0.0344 (12) | |
H16D | 0.7674 | 0.2411 | 0.2340 | 0.041* | |
C17D | 0.7082 (7) | 0.2155 (3) | 0.3255 (3) | 0.0367 (12) | |
C174 | 0.7795 (7) | 0.1494 (3) | 0.3351 (3) | 0.0417 (14) | |
H17J | 0.8823 | 0.1535 | 0.3344 | 0.063* | |
H17K | 0.7302 | 0.1208 | 0.2961 | 0.063* | |
H17L | 0.7722 | 0.1310 | 0.3812 | 0.063* | |
C18C | 1.1177 (7) | 0.2470 (3) | 0.3683 (3) | 0.0332 (12) | |
H18C | 1.1049 | 0.2204 | 0.4067 | 0.040* | |
N31D | 0.1003 (6) | 0.5382 (2) | 0.4713 (3) | 0.0346 (10) | |
C32D | 0.0662 (6) | 0.5585 (2) | 0.4060 (3) | 0.0338 (10) | |
H32D | 0.0798 | 0.5308 | 0.3687 | 0.041* | |
C33D | 0.0068 (5) | 0.6235 (3) | 0.3885 (3) | 0.0325 (10) | |
C34D | −0.0291 (6) | 0.6637 (3) | 0.4400 (3) | 0.0346 (12) | |
O34D | −0.0205 (5) | 0.6435 (2) | 0.50731 (19) | 0.0452 (9) | |
H34D | 0.0294 | 0.6094 | 0.5151 | 0.054* | |
C35D | −0.0770 (6) | 0.7271 (3) | 0.4209 (3) | 0.0385 (11) | |
H35D | −0.1054 | 0.7545 | 0.4549 | 0.046* | |
C36D | −0.0829 (6) | 0.7498 (3) | 0.3523 (3) | 0.0369 (12) | |
H36D | −0.1108 | 0.7935 | 0.3409 | 0.044* | |
C37D | −0.0493 (6) | 0.7108 (3) | 0.2998 (3) | 0.0362 (11) | |
C374 | −0.0547 (6) | 0.7378 (3) | 0.2262 (3) | 0.0427 (12) | |
H37J | −0.1523 | 0.7548 | 0.2053 | 0.064* | |
H37K | −0.0322 | 0.7033 | 0.1955 | 0.064* | |
H37L | 0.0170 | 0.7727 | 0.2301 | 0.064* | |
C38D | −0.0073 (5) | 0.6471 (2) | 0.3181 (3) | 0.0346 (10) | |
H38D | 0.0123 | 0.6190 | 0.2825 | 0.042* | |
C18D | 0.6336 (7) | 0.2383 (3) | 0.3741 (3) | 0.0334 (12) | |
H18D | 0.6301 | 0.2123 | 0.4145 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C37A | 0.040 (3) | 0.026 (2) | 0.048 (3) | 0.003 (2) | 0.003 (2) | 0.001 (2) |
C1A | 0.036 (3) | 0.025 (2) | 0.035 (3) | −0.006 (2) | 0.008 (2) | −0.003 (2) |
C2A | 0.031 (3) | 0.028 (2) | 0.033 (3) | −0.001 (2) | 0.007 (2) | 0.001 (2) |
C3A | 0.030 (3) | 0.023 (2) | 0.039 (3) | −0.004 (2) | 0.008 (2) | −0.001 (2) |
C4A | 0.034 (3) | 0.029 (3) | 0.034 (3) | −0.007 (2) | 0.005 (2) | −0.006 (2) |
C41A | 0.040 (3) | 0.034 (3) | 0.033 (3) | −0.008 (2) | 0.010 (2) | −0.004 (2) |
C5A | 0.039 (3) | 0.025 (2) | 0.034 (3) | −0.006 (2) | 0.008 (2) | −0.001 (2) |
C6A | 0.038 (3) | 0.022 (2) | 0.038 (3) | −0.002 (2) | 0.009 (2) | 0.001 (2) |
N11A | 0.036 (2) | 0.027 (2) | 0.035 (2) | −0.0001 (18) | 0.0085 (19) | −0.0033 (18) |
C12A | 0.041 (3) | 0.024 (2) | 0.031 (2) | −0.002 (2) | 0.009 (2) | 0.000 (2) |
C13A | 0.030 (3) | 0.028 (3) | 0.032 (3) | −0.001 (2) | 0.007 (2) | −0.004 (2) |
C14A | 0.036 (3) | 0.023 (2) | 0.035 (3) | 0.002 (2) | 0.002 (2) | 0.002 (2) |
O14A | 0.044 (2) | 0.033 (2) | 0.041 (2) | 0.0098 (17) | 0.0137 (18) | 0.0071 (17) |
C15A | 0.036 (3) | 0.037 (3) | 0.030 (3) | 0.001 (2) | 0.006 (2) | 0.002 (2) |
C16A | 0.039 (3) | 0.033 (3) | 0.039 (3) | 0.004 (2) | 0.007 (2) | −0.003 (2) |
C17A | 0.031 (3) | 0.027 (3) | 0.037 (3) | 0.001 (2) | 0.006 (2) | −0.001 (2) |
C171 | 0.040 (3) | 0.031 (3) | 0.045 (3) | 0.006 (2) | 0.008 (2) | −0.003 (2) |
C18A | 0.037 (3) | 0.019 (2) | 0.039 (3) | −0.003 (2) | 0.004 (2) | −0.001 (2) |
N31A | 0.036 (2) | 0.028 (2) | 0.032 (2) | 0.0011 (18) | 0.0096 (18) | 0.0008 (18) |
C32A | 0.037 (3) | 0.031 (2) | 0.036 (2) | 0.0025 (19) | 0.010 (2) | −0.002 (2) |
C33A | 0.035 (3) | 0.030 (2) | 0.041 (3) | −0.001 (2) | 0.009 (2) | −0.005 (2) |
C34A | 0.040 (3) | 0.033 (3) | 0.040 (3) | −0.002 (2) | 0.011 (2) | −0.010 (2) |
O34A | 0.048 (2) | 0.038 (2) | 0.055 (2) | 0.0035 (17) | 0.0192 (18) | −0.0021 (17) |
C35A | 0.042 (3) | 0.032 (3) | 0.054 (3) | 0.004 (2) | 0.013 (2) | −0.011 (2) |
C36A | 0.038 (3) | 0.028 (2) | 0.051 (3) | 0.006 (2) | 0.003 (2) | −0.009 (2) |
C371 | 0.051 (3) | 0.034 (3) | 0.054 (3) | 0.003 (2) | 0.007 (3) | 0.002 (2) |
C38A | 0.036 (3) | 0.030 (2) | 0.041 (3) | 0.002 (2) | 0.008 (2) | −0.002 (2) |
C1B | 0.037 (3) | 0.023 (2) | 0.036 (3) | −0.003 (2) | 0.010 (2) | 0.000 (2) |
C2B | 0.034 (3) | 0.026 (2) | 0.031 (2) | −0.002 (2) | 0.008 (2) | −0.001 (2) |
C3B | 0.034 (3) | 0.019 (2) | 0.036 (3) | 0.000 (2) | 0.007 (2) | 0.000 (2) |
C4B | 0.033 (3) | 0.024 (2) | 0.034 (3) | −0.005 (2) | 0.005 (2) | −0.002 (2) |
C41B | 0.042 (3) | 0.028 (2) | 0.031 (3) | −0.004 (2) | 0.011 (2) | −0.003 (2) |
C5B | 0.036 (3) | 0.026 (2) | 0.033 (3) | −0.002 (2) | 0.008 (2) | 0.004 (2) |
C6B | 0.038 (3) | 0.025 (2) | 0.039 (3) | −0.002 (2) | 0.009 (2) | 0.001 (2) |
N11B | 0.038 (2) | 0.025 (2) | 0.031 (2) | −0.0004 (18) | 0.0091 (18) | −0.0002 (17) |
C12B | 0.038 (3) | 0.021 (2) | 0.030 (2) | −0.001 (2) | 0.005 (2) | 0.0032 (19) |
C13B | 0.031 (3) | 0.025 (2) | 0.032 (3) | 0.000 (2) | 0.008 (2) | −0.002 (2) |
C14B | 0.040 (3) | 0.021 (2) | 0.031 (3) | 0.000 (2) | 0.002 (2) | 0.002 (2) |
O14B | 0.047 (2) | 0.0302 (19) | 0.042 (2) | 0.0089 (17) | 0.0167 (18) | 0.0090 (17) |
C15B | 0.037 (3) | 0.030 (3) | 0.029 (3) | −0.001 (2) | 0.007 (2) | 0.002 (2) |
C16B | 0.036 (3) | 0.028 (3) | 0.038 (3) | 0.001 (2) | 0.006 (2) | −0.004 (2) |
C17B | 0.029 (2) | 0.025 (2) | 0.036 (3) | −0.001 (2) | 0.007 (2) | −0.002 (2) |
C172 | 0.040 (3) | 0.025 (3) | 0.049 (3) | 0.004 (2) | 0.014 (2) | 0.000 (2) |
C18B | 0.036 (3) | 0.018 (2) | 0.034 (3) | −0.0022 (19) | 0.006 (2) | 0.0018 (19) |
N31B | 0.037 (2) | 0.023 (2) | 0.036 (2) | 0.0018 (18) | 0.0092 (18) | −0.0011 (18) |
C32B | 0.034 (2) | 0.026 (2) | 0.040 (2) | −0.0017 (18) | 0.011 (2) | −0.0032 (19) |
C33B | 0.031 (2) | 0.027 (2) | 0.040 (3) | −0.0001 (18) | 0.007 (2) | −0.004 (2) |
C34B | 0.036 (3) | 0.032 (3) | 0.035 (3) | 0.003 (2) | 0.005 (2) | −0.003 (2) |
O34B | 0.063 (3) | 0.0346 (19) | 0.0385 (18) | 0.0133 (18) | 0.0141 (17) | −0.0011 (16) |
C35B | 0.045 (3) | 0.028 (2) | 0.038 (2) | 0.005 (2) | 0.005 (2) | −0.006 (2) |
C36B | 0.038 (3) | 0.023 (2) | 0.044 (3) | 0.0023 (19) | 0.004 (2) | −0.003 (2) |
C37B | 0.037 (3) | 0.026 (2) | 0.041 (3) | 0.0013 (19) | 0.009 (2) | −0.001 (2) |
C372 | 0.049 (3) | 0.033 (3) | 0.045 (3) | 0.004 (2) | 0.014 (2) | 0.004 (2) |
C38B | 0.034 (2) | 0.028 (2) | 0.036 (2) | 0.0018 (18) | 0.0074 (18) | −0.0045 (19) |
C1C | 0.030 (3) | 0.027 (3) | 0.030 (2) | 0.000 (2) | 0.005 (2) | −0.004 (2) |
C2C | 0.039 (3) | 0.023 (2) | 0.034 (3) | −0.001 (2) | 0.009 (2) | 0.003 (2) |
C3C | 0.031 (3) | 0.030 (3) | 0.034 (3) | −0.002 (2) | 0.007 (2) | −0.003 (2) |
C4C | 0.029 (3) | 0.027 (2) | 0.037 (3) | −0.006 (2) | 0.009 (2) | −0.004 (2) |
C41C | 0.039 (3) | 0.031 (3) | 0.046 (3) | −0.002 (2) | 0.014 (2) | 0.001 (2) |
C5C | 0.041 (3) | 0.025 (3) | 0.036 (3) | −0.004 (2) | 0.010 (2) | −0.001 (2) |
C6C | 0.041 (3) | 0.026 (2) | 0.038 (3) | 0.003 (2) | 0.009 (2) | 0.002 (2) |
N11C | 0.033 (2) | 0.026 (2) | 0.034 (2) | −0.0012 (17) | 0.0062 (18) | −0.0033 (17) |
C12C | 0.034 (3) | 0.027 (3) | 0.034 (3) | −0.002 (2) | 0.006 (2) | 0.002 (2) |
C13C | 0.034 (3) | 0.025 (3) | 0.035 (3) | −0.004 (2) | 0.003 (2) | −0.001 (2) |
C14C | 0.033 (3) | 0.029 (3) | 0.038 (3) | 0.001 (2) | 0.009 (2) | −0.001 (2) |
O14C | 0.049 (3) | 0.030 (2) | 0.047 (2) | 0.0093 (17) | 0.0176 (19) | 0.0078 (17) |
C15C | 0.043 (3) | 0.033 (3) | 0.037 (3) | −0.001 (2) | 0.010 (2) | 0.002 (2) |
C16C | 0.034 (3) | 0.039 (3) | 0.036 (3) | 0.000 (2) | 0.012 (2) | −0.007 (2) |
C17C | 0.037 (3) | 0.026 (3) | 0.040 (3) | −0.002 (2) | 0.000 (2) | −0.006 (2) |
C173 | 0.049 (4) | 0.029 (3) | 0.055 (3) | −0.001 (3) | 0.008 (3) | −0.008 (3) |
N31C | 0.036 (2) | 0.027 (2) | 0.040 (2) | 0.0006 (18) | 0.0084 (19) | −0.0009 (19) |
C32C | 0.034 (3) | 0.028 (2) | 0.047 (3) | −0.0016 (19) | 0.012 (2) | −0.003 (2) |
C33C | 0.034 (3) | 0.027 (2) | 0.040 (3) | 0.004 (2) | 0.007 (2) | −0.001 (2) |
C34C | 0.039 (3) | 0.026 (2) | 0.044 (3) | −0.003 (2) | 0.008 (2) | −0.006 (2) |
O34C | 0.054 (2) | 0.0323 (19) | 0.054 (2) | 0.0067 (17) | 0.0250 (19) | 0.0041 (17) |
C35C | 0.040 (3) | 0.033 (3) | 0.054 (3) | 0.005 (2) | 0.014 (2) | −0.008 (2) |
C36C | 0.046 (3) | 0.024 (2) | 0.047 (3) | 0.005 (2) | 0.003 (2) | −0.004 (2) |
C37C | 0.044 (3) | 0.026 (2) | 0.043 (3) | −0.002 (2) | 0.005 (2) | −0.004 (2) |
C373 | 0.052 (3) | 0.028 (2) | 0.054 (3) | 0.002 (2) | 0.010 (3) | 0.006 (2) |
C38C | 0.036 (3) | 0.028 (2) | 0.045 (3) | −0.0009 (19) | 0.007 (2) | −0.004 (2) |
C1D | 0.031 (3) | 0.023 (2) | 0.032 (2) | −0.002 (2) | 0.008 (2) | −0.003 (2) |
C2D | 0.039 (3) | 0.026 (3) | 0.031 (2) | −0.003 (2) | 0.005 (2) | 0.002 (2) |
C3D | 0.032 (3) | 0.026 (2) | 0.030 (2) | −0.002 (2) | 0.004 (2) | −0.004 (2) |
C4D | 0.030 (3) | 0.028 (2) | 0.034 (3) | −0.005 (2) | 0.009 (2) | −0.001 (2) |
C41D | 0.043 (3) | 0.027 (2) | 0.042 (3) | −0.002 (2) | 0.015 (2) | −0.001 (2) |
C5D | 0.040 (3) | 0.023 (2) | 0.032 (2) | −0.004 (2) | 0.010 (2) | 0.003 (2) |
C6D | 0.041 (3) | 0.022 (2) | 0.038 (3) | −0.001 (2) | 0.010 (2) | 0.000 (2) |
N11D | 0.034 (2) | 0.022 (2) | 0.035 (2) | −0.0015 (17) | 0.0060 (19) | −0.0014 (16) |
C12D | 0.036 (3) | 0.025 (2) | 0.033 (3) | 0.000 (2) | 0.005 (2) | 0.002 (2) |
C13D | 0.030 (3) | 0.025 (2) | 0.034 (3) | −0.002 (2) | 0.001 (2) | 0.000 (2) |
C14D | 0.031 (3) | 0.026 (2) | 0.035 (3) | −0.001 (2) | 0.008 (2) | −0.003 (2) |
O14D | 0.046 (2) | 0.0242 (18) | 0.043 (2) | 0.0060 (16) | 0.0138 (18) | 0.0034 (16) |
C15D | 0.043 (3) | 0.029 (3) | 0.036 (3) | 0.001 (2) | 0.006 (2) | 0.001 (2) |
C16D | 0.038 (3) | 0.032 (3) | 0.034 (3) | 0.000 (2) | 0.012 (2) | −0.007 (2) |
C17D | 0.037 (3) | 0.029 (3) | 0.040 (3) | 0.002 (2) | 0.000 (2) | −0.006 (2) |
C174 | 0.048 (3) | 0.025 (3) | 0.049 (3) | 0.003 (2) | 0.006 (3) | −0.005 (2) |
C18C | 0.037 (3) | 0.029 (3) | 0.033 (3) | −0.004 (2) | 0.006 (2) | −0.001 (2) |
N31D | 0.036 (2) | 0.026 (2) | 0.041 (2) | −0.0010 (19) | 0.0090 (19) | −0.0028 (19) |
C32D | 0.040 (3) | 0.026 (2) | 0.037 (2) | −0.0018 (19) | 0.012 (2) | −0.0050 (19) |
C33D | 0.028 (2) | 0.028 (2) | 0.040 (3) | 0.0025 (19) | 0.0055 (19) | −0.002 (2) |
C34D | 0.036 (3) | 0.031 (2) | 0.033 (3) | 0.002 (2) | 0.002 (2) | −0.006 (2) |
O34D | 0.061 (3) | 0.040 (2) | 0.0353 (18) | 0.0166 (18) | 0.0132 (17) | 0.0007 (15) |
C35D | 0.039 (3) | 0.033 (3) | 0.041 (3) | 0.004 (2) | 0.006 (2) | −0.009 (2) |
C36D | 0.038 (3) | 0.025 (2) | 0.044 (3) | 0.003 (2) | 0.004 (2) | −0.002 (2) |
C37D | 0.034 (3) | 0.029 (2) | 0.043 (3) | 0.0004 (19) | 0.005 (2) | 0.000 (2) |
C374 | 0.049 (3) | 0.033 (3) | 0.045 (3) | 0.005 (2) | 0.009 (2) | 0.001 (2) |
C38D | 0.039 (3) | 0.026 (2) | 0.038 (2) | −0.0002 (19) | 0.0083 (19) | −0.0027 (19) |
C18D | 0.040 (3) | 0.024 (2) | 0.034 (3) | −0.002 (2) | 0.003 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
C37A—C38A | 1.383 (7) | C1C—C2C | 1.397 (8) |
C37A—C36A | 1.401 (8) | C1C—C6C | 1.400 (8) |
C37A—C371 | 1.500 (8) | C1C—N11C | 1.417 (7) |
C1A—C2A | 1.396 (8) | C2C—C3C | 1.392 (8) |
C1A—N11A | 1.405 (8) | C2C—H2C | 0.9500 |
C1A—C6A | 1.412 (8) | C3C—C4C | 1.403 (8) |
C2A—C3A | 1.392 (8) | C3C—N31C | 1.422 (7) |
C2A—H2A | 0.9500 | C4C—C5C | 1.396 (8) |
C3A—C4A | 1.405 (9) | C4C—C41C | 1.491 (8) |
C3A—N31A | 1.421 (7) | C41C—H41G | 0.9800 |
C4A—C5A | 1.391 (9) | C41C—H41H | 0.9800 |
C4A—C41A | 1.515 (8) | C41C—H41I | 0.9800 |
C41A—H41A | 0.9800 | C5C—C6C | 1.384 (9) |
C41A—H41B | 0.9800 | C5C—H5C | 0.9500 |
C41A—H41C | 0.9800 | C6C—H6C | 0.9500 |
C5A—C6A | 1.385 (8) | N11C—C12C | 1.289 (7) |
C5A—H5A | 0.9500 | C12C—C13C | 1.442 (8) |
C6A—H6A | 0.9500 | C12C—H12C | 0.9500 |
N11A—C12A | 1.281 (8) | C13C—C18C | 1.402 (8) |
C12A—C13A | 1.448 (8) | C13C—C14C | 1.409 (8) |
C12A—H12A | 0.9500 | C14C—O14C | 1.358 (7) |
C13A—C18A | 1.403 (8) | C14C—C15C | 1.382 (9) |
C13A—C14A | 1.411 (8) | O14C—H14C | 0.8400 |
C14A—O14A | 1.359 (7) | C15C—C16C | 1.389 (9) |
C14A—C15A | 1.392 (8) | C15C—H15C | 0.9500 |
O14A—H14A | 0.8400 | C16C—C17C | 1.392 (9) |
C15A—C16A | 1.371 (9) | C16C—H16C | 0.9500 |
C15A—H15A | 0.9500 | C17C—C18C | 1.385 (9) |
C16A—C17A | 1.413 (9) | C17C—C173 | 1.523 (8) |
C16A—H16A | 0.9500 | C173—H17G | 0.9800 |
C17A—C18A | 1.384 (8) | C173—H17H | 0.9800 |
C17A—C171 | 1.497 (8) | C173—H17I | 0.9800 |
C171—H17A | 0.9800 | N31C—C32C | 1.280 (7) |
C171—H17B | 0.9800 | C32C—C33C | 1.449 (7) |
C171—H17C | 0.9800 | C32C—H32C | 0.9500 |
C18A—H18A | 0.9500 | C33C—C34C | 1.398 (8) |
N31A—C32A | 1.281 (7) | C33C—C38C | 1.406 (7) |
C32A—C33A | 1.445 (7) | C34C—O34C | 1.350 (7) |
C32A—H32A | 0.9500 | C34C—C35C | 1.396 (8) |
C33A—C38A | 1.404 (7) | O34C—H34C | 0.8400 |
C33A—C34A | 1.416 (8) | C35C—C36C | 1.398 (8) |
C34A—O34A | 1.357 (7) | C35C—H35C | 0.9500 |
C34A—C35A | 1.394 (8) | C36C—C37C | 1.382 (8) |
O34A—H34A | 0.8400 | C36C—H36C | 0.9500 |
C35A—C36A | 1.383 (9) | C37C—C38C | 1.394 (7) |
C35A—H35A | 0.9500 | C37C—C373 | 1.509 (7) |
C36A—H36A | 0.9500 | C373—H37G | 0.9800 |
C371—H37A | 0.9800 | C373—H37H | 0.9800 |
C371—H37B | 0.9800 | C373—H37I | 0.9800 |
C371—H37C | 0.9800 | C38C—H38C | 0.9500 |
C38A—H38A | 0.9500 | C1D—C2D | 1.386 (8) |
C1B—C2B | 1.390 (8) | C1D—C6D | 1.400 (8) |
C1B—C6B | 1.409 (8) | C1D—N11D | 1.420 (7) |
C1B—N11B | 1.409 (8) | C2D—C3D | 1.396 (8) |
C2B—C3B | 1.394 (8) | C2D—H2D | 0.9500 |
C2B—H2B | 0.9500 | C3D—C4D | 1.404 (8) |
C3B—C4B | 1.408 (8) | C3D—N31D | 1.421 (7) |
C3B—N31B | 1.414 (7) | C4D—C5D | 1.394 (8) |
C4B—C5B | 1.399 (8) | C4D—C41D | 1.498 (8) |
C4B—C41B | 1.507 (8) | C41D—H41J | 0.9800 |
C41B—H41D | 0.9800 | C41D—H41K | 0.9800 |
C41B—H41E | 0.9800 | C41D—H41L | 0.9800 |
C41B—H41F | 0.9800 | C5D—C6D | 1.386 (8) |
C5B—C6B | 1.374 (8) | C5D—H5D | 0.9500 |
C5B—H5B | 0.9500 | C6D—H6D | 0.9500 |
C6B—H6B | 0.9500 | N11D—C12D | 1.288 (7) |
N11B—C12B | 1.280 (7) | C12D—C13D | 1.449 (8) |
C12B—C13B | 1.446 (8) | C12D—H12D | 0.9500 |
C12B—H12B | 0.9500 | C13D—C18D | 1.408 (8) |
C13B—C14B | 1.409 (8) | C13D—C14D | 1.413 (8) |
C13B—C18B | 1.411 (8) | C14D—O14D | 1.358 (7) |
C14B—O14B | 1.359 (7) | C14D—C15D | 1.380 (9) |
C14B—C15B | 1.389 (8) | O14D—H14D | 0.8400 |
O14B—H14B | 0.8400 | C15D—C16D | 1.386 (9) |
C15B—C16B | 1.385 (8) | C15D—H15D | 0.9500 |
C15B—H15B | 0.9500 | C16D—C17D | 1.398 (9) |
C16B—C17B | 1.408 (9) | C16D—H16D | 0.9500 |
C16B—H16B | 0.9500 | C17D—C18D | 1.382 (9) |
C17B—C18B | 1.381 (8) | C17D—C174 | 1.514 (8) |
C17B—C172 | 1.498 (8) | C174—H17J | 0.9800 |
C172—H17D | 0.9800 | C174—H17K | 0.9800 |
C172—H17E | 0.9800 | C174—H17L | 0.9800 |
C172—H17F | 0.9800 | C18C—H18C | 0.9500 |
C18B—H18B | 0.9500 | N31D—C32D | 1.287 (7) |
N31B—C32B | 1.286 (7) | C32D—C33D | 1.461 (7) |
C32B—C33B | 1.453 (7) | C32D—H32D | 0.9500 |
C32B—H32B | 0.9500 | C33D—C34D | 1.397 (8) |
C33B—C38B | 1.398 (7) | C33D—C38D | 1.414 (7) |
C33B—C34B | 1.407 (7) | C34D—O34D | 1.342 (7) |
C34B—O34B | 1.354 (7) | C34D—C35D | 1.405 (8) |
C34B—C35B | 1.397 (7) | O34D—H34D | 0.8400 |
O34B—H34B | 0.8400 | C35D—C36D | 1.387 (8) |
C35B—C36B | 1.381 (8) | C35D—H35D | 0.9500 |
C35B—H35B | 0.9500 | C36D—C37D | 1.386 (8) |
C36B—C37B | 1.403 (8) | C36D—H36D | 0.9500 |
C36B—H36B | 0.9500 | C37D—C38D | 1.393 (7) |
C37B—C38B | 1.384 (7) | C37D—C374 | 1.509 (7) |
C37B—C372 | 1.496 (7) | C374—H37J | 0.9800 |
C372—H37D | 0.9800 | C374—H37K | 0.9800 |
C372—H37E | 0.9800 | C374—H37L | 0.9800 |
C372—H37F | 0.9800 | C38D—H38D | 0.9500 |
C38B—H38B | 0.9500 | C18D—H18D | 0.9500 |
| | | |
C38A—C37A—C36A | 117.0 (5) | C2C—C1C—C6C | 117.8 (5) |
C38A—C37A—C371 | 122.1 (5) | C2C—C1C—N11C | 116.2 (5) |
C36A—C37A—C371 | 120.9 (5) | C6C—C1C—N11C | 126.0 (5) |
C2A—C1A—N11A | 116.2 (5) | C3C—C2C—C1C | 121.5 (5) |
C2A—C1A—C6A | 118.3 (6) | C3C—C2C—H2C | 119.2 |
N11A—C1A—C6A | 125.5 (5) | C1C—C2C—H2C | 119.2 |
C3A—C2A—C1A | 121.9 (5) | C2C—C3C—C4C | 120.5 (5) |
C3A—C2A—H2A | 119.1 | C2C—C3C—N31C | 121.5 (5) |
C1A—C2A—H2A | 119.1 | C4C—C3C—N31C | 117.9 (5) |
C2A—C3A—C4A | 120.2 (5) | C5C—C4C—C3C | 117.6 (5) |
C2A—C3A—N31A | 121.8 (5) | C5C—C4C—C41C | 120.4 (5) |
C4A—C3A—N31A | 118.0 (5) | C3C—C4C—C41C | 122.0 (5) |
C5A—C4A—C3A | 117.3 (6) | C4C—C41C—H41G | 109.5 |
C5A—C4A—C41A | 121.9 (5) | C4C—C41C—H41H | 109.5 |
C3A—C4A—C41A | 120.8 (5) | H41G—C41C—H41H | 109.5 |
C4A—C41A—H41A | 109.5 | C4C—C41C—H41I | 109.5 |
C4A—C41A—H41B | 109.5 | H41G—C41C—H41I | 109.5 |
H41A—C41A—H41B | 109.5 | H41H—C41C—H41I | 109.5 |
C4A—C41A—H41C | 109.5 | C6C—C5C—C4C | 121.9 (5) |
H41A—C41A—H41C | 109.5 | C6C—C5C—H5C | 119.1 |
H41B—C41A—H41C | 109.5 | C4C—C5C—H5C | 119.1 |
C6A—C5A—C4A | 123.6 (5) | C5C—C6C—C1C | 120.7 (5) |
C6A—C5A—H5A | 118.2 | C5C—C6C—H6C | 119.7 |
C4A—C5A—H5A | 118.2 | C1C—C6C—H6C | 119.7 |
C5A—C6A—C1A | 118.8 (5) | C12C—N11C—C1C | 121.7 (5) |
C5A—C6A—H6A | 120.6 | N11C—C12C—C13C | 122.5 (5) |
C1A—C6A—H6A | 120.6 | N11C—C12C—H12C | 118.7 |
C12A—N11A—C1A | 122.0 (5) | C13C—C12C—H12C | 118.7 |
N11A—C12A—C13A | 121.4 (5) | C18C—C13C—C14C | 118.8 (6) |
N11A—C12A—H12A | 119.3 | C18C—C13C—C12C | 119.1 (5) |
C13A—C12A—H12A | 119.3 | C14C—C13C—C12C | 122.0 (5) |
C18A—C13A—C14A | 118.3 (5) | O14C—C14C—C15C | 119.2 (5) |
C18A—C13A—C12A | 119.3 (5) | O14C—C14C—C13C | 121.4 (5) |
C14A—C13A—C12A | 122.5 (5) | C15C—C14C—C13C | 119.3 (5) |
O14A—C14A—C15A | 118.6 (5) | C14C—O14C—H14C | 109.5 |
O14A—C14A—C13A | 121.4 (6) | C14C—C15C—C16C | 120.5 (5) |
C15A—C14A—C13A | 120.0 (5) | C14C—C15C—H15C | 119.7 |
C14A—O14A—H14A | 109.5 | C16C—C15C—H15C | 119.7 |
C16A—C15A—C14A | 120.0 (5) | C15C—C16C—C17C | 121.6 (6) |
C16A—C15A—H15A | 120.0 | C15C—C16C—H16C | 119.2 |
C14A—C15A—H15A | 120.0 | C17C—C16C—H16C | 119.2 |
C15A—C16A—C17A | 122.0 (6) | C18C—C17C—C16C | 117.7 (5) |
C15A—C16A—H16A | 119.0 | C18C—C17C—C173 | 120.4 (6) |
C17A—C16A—H16A | 119.0 | C16C—C17C—C173 | 121.9 (6) |
C18A—C17A—C16A | 117.2 (5) | C17C—C173—H17G | 109.5 |
C18A—C17A—C171 | 122.0 (5) | C17C—C173—H17H | 109.5 |
C16A—C17A—C171 | 120.8 (5) | H17G—C173—H17H | 109.5 |
C17A—C171—H17A | 109.5 | C17C—C173—H17I | 109.5 |
C17A—C171—H17B | 109.5 | H17G—C173—H17I | 109.5 |
H17A—C171—H17B | 109.5 | H17H—C173—H17I | 109.5 |
C17A—C171—H17C | 109.5 | C32C—N31C—C3C | 120.1 (5) |
H17A—C171—H17C | 109.5 | N31C—C32C—C33C | 122.3 (5) |
H17B—C171—H17C | 109.5 | N31C—C32C—H32C | 118.9 |
C17A—C18A—C13A | 122.5 (5) | C33C—C32C—H32C | 118.9 |
C17A—C18A—H18A | 118.7 | C34C—C33C—C38C | 119.3 (5) |
C13A—C18A—H18A | 118.7 | C34C—C33C—C32C | 121.8 (5) |
C32A—N31A—C3A | 120.7 (5) | C38C—C33C—C32C | 118.8 (5) |
N31A—C32A—C33A | 122.8 (5) | O34C—C34C—C35C | 118.7 (5) |
N31A—C32A—H32A | 118.6 | O34C—C34C—C33C | 122.0 (5) |
C33A—C32A—H32A | 118.6 | C35C—C34C—C33C | 119.3 (5) |
C38A—C33A—C34A | 118.6 (5) | C34C—O34C—H34C | 109.5 |
C38A—C33A—C32A | 119.6 (5) | C34C—C35C—C36C | 119.8 (5) |
C34A—C33A—C32A | 121.6 (5) | C34C—C35C—H35C | 120.1 |
O34A—C34A—C35A | 119.3 (5) | C36C—C35C—H35C | 120.1 |
O34A—C34A—C33A | 121.6 (5) | C37C—C36C—C35C | 122.4 (5) |
C35A—C34A—C33A | 119.1 (5) | C37C—C36C—H36C | 118.8 |
C34A—O34A—H34A | 109.5 | C35C—C36C—H36C | 118.8 |
C36A—C35A—C34A | 120.2 (5) | C36C—C37C—C38C | 117.2 (5) |
C36A—C35A—H35A | 119.9 | C36C—C37C—C373 | 122.0 (5) |
C34A—C35A—H35A | 119.9 | C38C—C37C—C373 | 120.8 (5) |
C35A—C36A—C37A | 122.2 (5) | C37C—C373—H37G | 109.5 |
C35A—C36A—H36A | 118.9 | C37C—C373—H37H | 109.5 |
C37A—C36A—H36A | 118.9 | H37G—C373—H37H | 109.5 |
C37A—C371—H37A | 109.5 | C37C—C373—H37I | 109.5 |
C37A—C371—H37B | 109.5 | H37G—C373—H37I | 109.5 |
H37A—C371—H37B | 109.5 | H37H—C373—H37I | 109.5 |
C37A—C371—H37C | 109.5 | C37C—C38C—C33C | 122.1 (5) |
H37A—C371—H37C | 109.5 | C37C—C38C—H38C | 118.9 |
H37B—C371—H37C | 109.5 | C33C—C38C—H38C | 118.9 |
C37A—C38A—C33A | 122.8 (5) | C2D—C1D—C6D | 118.3 (5) |
C37A—C38A—H38A | 118.6 | C2D—C1D—N11D | 115.4 (5) |
C33A—C38A—H38A | 118.6 | C6D—C1D—N11D | 126.2 (5) |
C2B—C1B—C6B | 117.9 (6) | C1D—C2D—C3D | 121.7 (5) |
C2B—C1B—N11B | 116.2 (5) | C1D—C2D—H2D | 119.1 |
C6B—C1B—N11B | 125.9 (5) | C3D—C2D—H2D | 119.1 |
C1B—C2B—C3B | 122.2 (5) | C2D—C3D—C4D | 120.1 (5) |
C1B—C2B—H2B | 118.9 | C2D—C3D—N31D | 121.6 (5) |
C3B—C2B—H2B | 118.9 | C4D—C3D—N31D | 118.2 (5) |
C2B—C3B—C4B | 120.1 (5) | C5D—C4D—C3D | 117.5 (5) |
C2B—C3B—N31B | 122.1 (5) | C5D—C4D—C41D | 120.6 (5) |
C4B—C3B—N31B | 117.7 (5) | C3D—C4D—C41D | 121.8 (5) |
C5B—C4B—C3B | 116.7 (5) | C4D—C41D—H41J | 109.5 |
C5B—C4B—C41B | 121.2 (5) | C4D—C41D—H41K | 109.5 |
C3B—C4B—C41B | 122.0 (5) | H41J—C41D—H41K | 109.5 |
C4B—C41B—H41D | 109.5 | C4D—C41D—H41L | 109.5 |
C4B—C41B—H41E | 109.5 | H41J—C41D—H41L | 109.5 |
H41D—C41B—H41E | 109.5 | H41K—C41D—H41L | 109.5 |
C4B—C41B—H41F | 109.5 | C6D—C5D—C4D | 122.3 (5) |
H41D—C41B—H41F | 109.5 | C6D—C5D—H5D | 118.8 |
H41E—C41B—H41F | 109.5 | C4D—C5D—H5D | 118.8 |
C6B—C5B—C4B | 123.5 (5) | C5D—C6D—C1D | 119.9 (5) |
C6B—C5B—H5B | 118.2 | C5D—C6D—H6D | 120.1 |
C4B—C5B—H5B | 118.2 | C1D—C6D—H6D | 120.1 |
C5B—C6B—C1B | 119.6 (5) | C12D—N11D—C1D | 122.3 (5) |
C5B—C6B—H6B | 120.2 | N11D—C12D—C13D | 121.9 (5) |
C1B—C6B—H6B | 120.2 | N11D—C12D—H12D | 119.1 |
C12B—N11B—C1B | 121.7 (5) | C13D—C12D—H12D | 119.1 |
N11B—C12B—C13B | 122.0 (5) | C18D—C13D—C14D | 118.7 (6) |
N11B—C12B—H12B | 119.0 | C18D—C13D—C12D | 119.8 (5) |
C13B—C12B—H12B | 119.0 | C14D—C13D—C12D | 121.5 (5) |
C14B—C13B—C18B | 118.1 (5) | O14D—C14D—C15D | 118.8 (5) |
C14B—C13B—C12B | 122.6 (5) | O14D—C14D—C13D | 122.1 (5) |
C18B—C13B—C12B | 119.3 (5) | C15D—C14D—C13D | 119.2 (5) |
O14B—C14B—C15B | 118.9 (5) | C14D—O14D—H14D | 109.5 |
O14B—C14B—C13B | 120.9 (5) | C14D—C15D—C16D | 121.0 (5) |
C15B—C14B—C13B | 120.3 (5) | C14D—C15D—H15D | 119.5 |
C14B—O14B—H14B | 109.5 | C16D—C15D—H15D | 119.5 |
C16B—C15B—C14B | 120.0 (5) | C15D—C16D—C17D | 121.2 (6) |
C16B—C15B—H15B | 120.0 | C15D—C16D—H16D | 119.4 |
C14B—C15B—H15B | 120.0 | C17D—C16D—H16D | 119.4 |
C15B—C16B—C17B | 121.6 (6) | C18D—C17D—C16D | 117.9 (5) |
C15B—C16B—H16B | 119.2 | C18D—C17D—C174 | 120.6 (6) |
C17B—C16B—H16B | 119.2 | C16D—C17D—C174 | 121.5 (6) |
C18B—C17B—C16B | 117.6 (5) | C17D—C174—H17J | 109.5 |
C18B—C17B—C172 | 121.9 (5) | C17D—C174—H17K | 109.5 |
C16B—C17B—C172 | 120.5 (5) | H17J—C174—H17K | 109.5 |
C17B—C172—H17D | 109.5 | C17D—C174—H17L | 109.5 |
C17B—C172—H17E | 109.5 | H17J—C174—H17L | 109.5 |
H17D—C172—H17E | 109.5 | H17K—C174—H17L | 109.5 |
C17B—C172—H17F | 109.5 | C17C—C18C—C13C | 122.1 (5) |
H17D—C172—H17F | 109.5 | C17C—C18C—H18C | 119.0 |
H17E—C172—H17F | 109.5 | C13C—C18C—H18C | 119.0 |
C17B—C18B—C13B | 122.4 (5) | C32D—N31D—C3D | 119.8 (5) |
C17B—C18B—H18B | 118.8 | N31D—C32D—C33D | 121.1 (5) |
C13B—C18B—H18B | 118.8 | N31D—C32D—H32D | 119.5 |
C32B—N31B—C3B | 120.0 (5) | C33D—C32D—H32D | 119.5 |
N31B—C32B—C33B | 122.4 (5) | C34D—C33D—C38D | 119.4 (5) |
N31B—C32B—H32B | 118.8 | C34D—C33D—C32D | 121.9 (5) |
C33B—C32B—H32B | 118.8 | C38D—C33D—C32D | 118.7 (4) |
C38B—C33B—C34B | 118.9 (5) | O34D—C34D—C33D | 121.9 (5) |
C38B—C33B—C32B | 120.2 (5) | O34D—C34D—C35D | 119.0 (5) |
C34B—C33B—C32B | 120.8 (5) | C33D—C34D—C35D | 119.1 (5) |
O34B—C34B—C35B | 118.9 (5) | C34D—O34D—H34D | 109.5 |
O34B—C34B—C33B | 121.6 (5) | C36D—C35D—C34D | 120.0 (5) |
C35B—C34B—C33B | 119.5 (5) | C36D—C35D—H35D | 120.0 |
C34B—O34B—H34B | 109.5 | C34D—C35D—H35D | 120.0 |
C36B—C35B—C34B | 119.7 (5) | C37D—C36D—C35D | 122.1 (5) |
C36B—C35B—H35B | 120.1 | C37D—C36D—H36D | 118.9 |
C34B—C35B—H35B | 120.1 | C35D—C36D—H36D | 118.9 |
C35B—C36B—C37B | 122.2 (5) | C36D—C37D—C38D | 117.8 (5) |
C35B—C36B—H36B | 118.9 | C36D—C37D—C374 | 120.4 (5) |
C37B—C36B—H36B | 118.9 | C38D—C37D—C374 | 121.9 (5) |
C38B—C37B—C36B | 117.1 (5) | C37D—C374—H37J | 109.5 |
C38B—C37B—C372 | 123.2 (5) | C37D—C374—H37K | 109.5 |
C36B—C37B—C372 | 119.7 (5) | H37J—C374—H37K | 109.5 |
C37B—C372—H37D | 109.5 | C37D—C374—H37L | 109.5 |
C37B—C372—H37E | 109.5 | H37J—C374—H37L | 109.5 |
H37D—C372—H37E | 109.5 | H37K—C374—H37L | 109.5 |
C37B—C372—H37F | 109.5 | C37D—C38D—C33D | 121.5 (5) |
H37D—C372—H37F | 109.5 | C37D—C38D—H38D | 119.2 |
H37E—C372—H37F | 109.5 | C33D—C38D—H38D | 119.2 |
C37B—C38B—C33B | 122.5 (5) | C17D—C18D—C13D | 122.0 (5) |
C37B—C38B—H38B | 118.8 | C17D—C18D—H18D | 119.0 |
C33B—C38B—H38B | 118.8 | C13D—C18D—H18D | 119.0 |
| | | |
N11A—C1A—C2A—C3A | 177.7 (5) | C6C—C1C—C2C—C3C | 1.9 (9) |
C6A—C1A—C2A—C3A | −2.2 (8) | N11C—C1C—C2C—C3C | −175.9 (5) |
C1A—C2A—C3A—C4A | 3.0 (9) | C1C—C2C—C3C—C4C | −2.1 (9) |
C1A—C2A—C3A—N31A | −179.7 (5) | C1C—C2C—C3C—N31C | −179.2 (5) |
C2A—C3A—C4A—C5A | −2.0 (8) | C2C—C3C—C4C—C5C | 0.7 (8) |
N31A—C3A—C4A—C5A | −179.3 (5) | N31C—C3C—C4C—C5C | 177.9 (5) |
C2A—C3A—C4A—C41A | −179.9 (5) | C2C—C3C—C4C—C41C | −179.6 (5) |
N31A—C3A—C4A—C41A | 2.7 (8) | N31C—C3C—C4C—C41C | −2.4 (8) |
C3A—C4A—C5A—C6A | 0.2 (8) | C3C—C4C—C5C—C6C | 0.9 (9) |
C41A—C4A—C5A—C6A | 178.1 (5) | C41C—C4C—C5C—C6C | −178.8 (5) |
C4A—C5A—C6A—C1A | 0.6 (9) | C4C—C5C—C6C—C1C | −1.0 (9) |
C2A—C1A—C6A—C5A | 0.4 (8) | C2C—C1C—C6C—C5C | −0.3 (9) |
N11A—C1A—C6A—C5A | −179.5 (5) | N11C—C1C—C6C—C5C | 177.2 (5) |
C2A—C1A—N11A—C12A | 175.6 (5) | C2C—C1C—N11C—C12C | −170.7 (5) |
C6A—C1A—N11A—C12A | −4.5 (9) | C6C—C1C—N11C—C12C | 11.7 (9) |
C1A—N11A—C12A—C13A | 177.6 (5) | C1C—N11C—C12C—C13C | −176.3 (5) |
N11A—C12A—C13A—C18A | 178.4 (5) | N11C—C12C—C13C—C18C | 175.1 (5) |
N11A—C12A—C13A—C14A | −0.6 (9) | N11C—C12C—C13C—C14C | −3.4 (9) |
C18A—C13A—C14A—O14A | 179.9 (5) | C18C—C13C—C14C—O14C | 180.0 (5) |
C12A—C13A—C14A—O14A | −1.1 (9) | C12C—C13C—C14C—O14C | −1.5 (9) |
C18A—C13A—C14A—C15A | 0.9 (8) | C18C—C13C—C14C—C15C | 1.8 (9) |
C12A—C13A—C14A—C15A | 179.9 (5) | C12C—C13C—C14C—C15C | −179.7 (6) |
O14A—C14A—C15A—C16A | 179.7 (5) | O14C—C14C—C15C—C16C | −179.7 (6) |
C13A—C14A—C15A—C16A | −1.3 (9) | C13C—C14C—C15C—C16C | −1.5 (9) |
C14A—C15A—C16A—C17A | 0.5 (10) | C14C—C15C—C16C—C17C | 0.4 (10) |
C15A—C16A—C17A—C18A | 0.7 (9) | C15C—C16C—C17C—C18C | 0.3 (9) |
C15A—C16A—C17A—C171 | −179.5 (6) | C15C—C16C—C17C—C173 | −179.2 (6) |
C16A—C17A—C18A—C13A | −1.1 (8) | C2C—C3C—N31C—C32C | −25.5 (8) |
C171—C17A—C18A—C13A | 179.1 (5) | C4C—C3C—N31C—C32C | 157.4 (5) |
C14A—C13A—C18A—C17A | 0.3 (8) | C3C—N31C—C32C—C33C | 173.4 (5) |
C12A—C13A—C18A—C17A | −178.7 (5) | N31C—C32C—C33C—C34C | 6.3 (8) |
C2A—C3A—N31A—C32A | 25.8 (8) | N31C—C32C—C33C—C38C | −170.0 (5) |
C4A—C3A—N31A—C32A | −157.0 (5) | C38C—C33C—C34C—O34C | 179.0 (5) |
C3A—N31A—C32A—C33A | −174.6 (5) | C32C—C33C—C34C—O34C | 2.7 (8) |
N31A—C32A—C33A—C38A | 168.8 (5) | C38C—C33C—C34C—C35C | −0.5 (8) |
N31A—C32A—C33A—C34A | −6.8 (8) | C32C—C33C—C34C—C35C | −176.9 (5) |
C38A—C33A—C34A—O34A | −178.7 (5) | O34C—C34C—C35C—C36C | −178.3 (5) |
C32A—C33A—C34A—O34A | −3.0 (8) | C33C—C34C—C35C—C36C | 1.3 (9) |
C38A—C33A—C34A—C35A | 1.4 (8) | C34C—C35C—C36C—C37C | −1.1 (9) |
C32A—C33A—C34A—C35A | 177.0 (5) | C35C—C36C—C37C—C38C | 0.1 (8) |
O34A—C34A—C35A—C36A | 177.9 (5) | C35C—C36C—C37C—C373 | 177.9 (5) |
C33A—C34A—C35A—C36A | −2.1 (8) | C36C—C37C—C38C—C33C | 0.7 (8) |
C34A—C35A—C36A—C37A | 1.5 (9) | C373—C37C—C38C—C33C | −177.2 (5) |
C38A—C37A—C36A—C35A | −0.1 (8) | C34C—C33C—C38C—C37C | −0.5 (8) |
C371—C37A—C36A—C35A | −178.6 (6) | C32C—C33C—C38C—C37C | 176.0 (5) |
C36A—C37A—C38A—C33A | −0.7 (8) | C6D—C1D—C2D—C3D | −2.3 (8) |
C371—C37A—C38A—C33A | 177.8 (5) | N11D—C1D—C2D—C3D | −179.7 (5) |
C34A—C33A—C38A—C37A | 0.0 (8) | C1D—C2D—C3D—C4D | 4.2 (8) |
C32A—C33A—C38A—C37A | −175.7 (5) | C1D—C2D—C3D—N31D | 179.4 (5) |
C6B—C1B—C2B—C3B | 1.9 (9) | C2D—C3D—C4D—C5D | −3.8 (8) |
N11B—C1B—C2B—C3B | 179.7 (5) | N31D—C3D—C4D—C5D | −179.2 (5) |
C1B—C2B—C3B—C4B | −3.6 (9) | C2D—C3D—C4D—C41D | 176.6 (5) |
C1B—C2B—C3B—N31B | 179.2 (5) | N31D—C3D—C4D—C41D | 1.2 (8) |
C2B—C3B—C4B—C5B | 3.0 (8) | C3D—C4D—C5D—C6D | 1.8 (8) |
N31B—C3B—C4B—C5B | −179.6 (5) | C41D—C4D—C5D—C6D | −178.6 (5) |
C2B—C3B—C4B—C41B | −174.7 (5) | C4D—C5D—C6D—C1D | 0.0 (9) |
N31B—C3B—C4B—C41B | 2.7 (8) | C2D—C1D—C6D—C5D | 0.2 (8) |
C3B—C4B—C5B—C6B | −0.9 (8) | N11D—C1D—C6D—C5D | 177.2 (5) |
C41B—C4B—C5B—C6B | 176.8 (5) | C2D—C1D—N11D—C12D | −175.2 (5) |
C4B—C5B—C6B—C1B | −0.7 (9) | C6D—C1D—N11D—C12D | 7.7 (9) |
C2B—C1B—C6B—C5B | 0.2 (8) | C1D—N11D—C12D—C13D | 179.3 (5) |
N11B—C1B—C6B—C5B | −177.4 (5) | N11D—C12D—C13D—C18D | −180.0 (5) |
C2B—C1B—N11B—C12B | 173.6 (5) | N11D—C12D—C13D—C14D | −1.3 (9) |
C6B—C1B—N11B—C12B | −8.8 (9) | C18D—C13D—C14D—O14D | 178.7 (5) |
C1B—N11B—C12B—C13B | 177.8 (5) | C12D—C13D—C14D—O14D | 0.0 (9) |
N11B—C12B—C13B—C14B | 4.9 (9) | C18D—C13D—C14D—C15D | −0.2 (8) |
N11B—C12B—C13B—C18B | −175.4 (5) | C12D—C13D—C14D—C15D | −178.8 (5) |
C18B—C13B—C14B—O14B | −179.7 (5) | O14D—C14D—C15D—C16D | −178.5 (5) |
C12B—C13B—C14B—O14B | 0.0 (9) | C13D—C14D—C15D—C16D | 0.4 (9) |
C18B—C13B—C14B—C15B | 0.7 (8) | C14D—C15D—C16D—C17D | 0.4 (10) |
C12B—C13B—C14B—C15B | −179.6 (5) | C15D—C16D—C17D—C18D | −1.4 (9) |
O14B—C14B—C15B—C16B | 179.6 (5) | C15D—C16D—C17D—C174 | 178.4 (6) |
C13B—C14B—C15B—C16B | −0.8 (9) | C16C—C17C—C18C—C13C | 0.1 (9) |
C14B—C15B—C16B—C17B | 1.1 (9) | C173—C17C—C18C—C13C | 179.6 (5) |
C15B—C16B—C17B—C18B | −1.2 (9) | C14C—C13C—C18C—C17C | −1.1 (9) |
C15B—C16B—C17B—C172 | −179.5 (5) | C12C—C13C—C18C—C17C | −179.7 (5) |
C16B—C17B—C18B—C13B | 1.1 (8) | C2D—C3D—N31D—C32D | 23.5 (8) |
C172—C17B—C18B—C13B | 179.4 (5) | C4D—C3D—N31D—C32D | −161.2 (5) |
C14B—C13B—C18B—C17B | −0.9 (8) | C3D—N31D—C32D—C33D | −171.6 (5) |
C12B—C13B—C18B—C17B | 179.4 (5) | N31D—C32D—C33D—C34D | −6.5 (8) |
C2B—C3B—N31B—C32B | −22.6 (8) | N31D—C32D—C33D—C38D | 170.1 (5) |
C4B—C3B—N31B—C32B | 160.1 (5) | C38D—C33D—C34D—O34D | 178.7 (5) |
C3B—N31B—C32B—C33B | 170.8 (5) | C32D—C33D—C34D—O34D | −4.7 (8) |
N31B—C32B—C33B—C38B | −169.6 (5) | C38D—C33D—C34D—C35D | −0.6 (8) |
N31B—C32B—C33B—C34B | 5.4 (8) | C32D—C33D—C34D—C35D | 176.0 (5) |
C38B—C33B—C34B—O34B | 179.8 (5) | O34D—C34D—C35D—C36D | 178.2 (5) |
C32B—C33B—C34B—O34B | 4.7 (8) | C33D—C34D—C35D—C36D | −2.5 (8) |
C38B—C33B—C34B—C35B | −1.4 (8) | C34D—C35D—C36D—C37D | 3.1 (9) |
C32B—C33B—C34B—C35B | −176.5 (5) | C35D—C36D—C37D—C38D | −0.6 (8) |
O34B—C34B—C35B—C36B | −178.2 (5) | C35D—C36D—C37D—C374 | −179.0 (5) |
C33B—C34B—C35B—C36B | 2.9 (8) | C36D—C37D—C38D—C33D | −2.6 (8) |
C34B—C35B—C36B—C37B | −1.4 (9) | C374—C37D—C38D—C33D | 175.8 (5) |
C35B—C36B—C37B—C38B | −1.7 (8) | C34D—C33D—C38D—C37D | 3.2 (8) |
C35B—C36B—C37B—C372 | 178.6 (5) | C32D—C33D—C38D—C37D | −173.5 (5) |
C36B—C37B—C38B—C33B | 3.3 (8) | C16D—C17D—C18D—C13D | 1.6 (9) |
C372—C37B—C38B—C33B | −177.0 (5) | C174—C17D—C18D—C13D | −178.2 (5) |
C34B—C33B—C38B—C37B | −1.8 (8) | C14D—C13D—C18D—C17D | −0.8 (9) |
C32B—C33B—C38B—C37B | 173.3 (5) | C12D—C13D—C18D—C17D | 177.8 (5) |
Experimental details
| (1) | (2) | (3) |
Crystal data |
Chemical formula | C23H22N2O2 | C23H22N2O2 | C23H22N2O2 |
Mr | 358.42 | 358.42 | 358.42 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21 |
Temperature (K) | 295 | 295 | 130 |
a, b, c (Å) | 4.810 (2), 20.601 (3), 18.831 (3) | 21.694 (3), 12.599 (2), 21.236 (3) | 9.464 (2), 20.640 (3), 19.219 (3) |
β (°) | 91.95 (2) | 93.38 (2) | 103.93 (2) |
V (Å3) | 1864.9 (9) | 5794.2 (15) | 3643.8 (11) |
Z | 4 | 12 | 8 |
Radiation type | Mo Kα | Cu Kα | Cu Kα |
µ (mm−1) | 0.08 | 0.63 | 0.67 |
Crystal size (mm) | 0.35 × 0.2 × 0.1 | 0.25 × 0.1 × 0.1 | 0.2 × 0.15 × 0.1 |
|
Data collection |
Diffractometer | Xcalibur, Sapphire2, large Be window diffractometer | SuperNova, Single source at offset), Atlas diffractometer | SuperNova, Single source at offset), Atlas diffractometer |
Absorption correction | Multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | Multi-scan CrysAlis PRO, Oxford Diffraction Ltd.,
Version 1.171.34.43 (release 21-10-2010 CrysAlis171 .NET)
(compiled Oct 21 2010,17:48:23)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. |
Tmin, Tmax | 0.920, 1.000 | 0.332, 1.000 | 0.920, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20558, 3286, 1408 | 28367, 10386, 5091 | 27193, 12478, 9327 |
Rint | 0.088 | 0.043 | 0.064 |
(sin θ/λ)max (Å−1) | 0.595 | 0.599 | 0.625 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.078, 0.192, 1.01 | 0.078, 0.220, 1.07 | 0.063, 0.188, 1.02 |
No. of reflections | 3286 | 10386 | 12478 |
No. of parameters | 251 | 745 | 993 |
No. of restraints | 0 | 0 | 1 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.29 | 0.29, −0.21 | 0.31, −0.26 |
Absolute structure | ? | ? | Classical Flack method preferred over Parsons because s.u. lower. |
Absolute structure parameter | ? | ? | 0.5 (4) |
Hydrogen-bond geometry (Å, º) for (1) top
D—H···A | D—H | H···A | D···A | D—H···A |
O14—H14···N11 | 0.99 | 1.71 | 2.612 (4) | 150.1 |
O34—H34···N31 | 0.95 | 1.83 | 2.570 (5) | 132.4 |
C371—H37C···O14i | 0.96 | 2.59 | 3.477 (6) | 153.4 |
C18—H18···O34ii | 0.93 | 2.62 | 3.541 (5) | 171.8 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, y−1/2, −z+3/2. |
Hydrogen-bond geometry (Å, º) for (2) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18A—H18A···O14Bi | 0.93 | 2.60 | 3.531 (4) | 175.1 |
C36A—H36A···O34B | 0.93 | 2.63 | 3.536 (5) | 163.9 |
C18B—H18B···O14Aii | 0.93 | 2.49 | 3.377 (4) | 159.5 |
C36B—H36B···O34Aiii | 0.93 | 2.59 | 3.496 (4) | 166.6 |
C173—H17G···O14Aii | 0.96 | 2.68 | 3.603 (5) | 162.0 |
C18C—H18C···O14Civ | 0.93 | 2.66 | 3.564 (4) | 165.4 |
C36C—H36C···O34Cv | 0.93 | 2.61 | 3.512 (4) | 162.6 |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y, z; (iii) x, y−1, z; (iv) −x, y+1/2, −z+3/2; (v) −x+1, y−1/2, −z+3/2. |
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