Supramolecular synthesis based on piperidone derivatives and pharmaceutically acceptable co-formers
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113006185/qs3023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006185/qs3023IIIsup4.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006185/qs3023IIsup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006185/qs3023IIIsup6.cml |
CCDC references: 934618; 934619; 934620
For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C27H35N3O·CH4O | F(000) = 976 |
Mr = 449.62 | Dx = 1.195 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 7753 reflections |
a = 14.8473 (5) Å | θ = 2.8–30.3° |
b = 7.7578 (3) Å | µ = 0.08 mm−1 |
c = 21.8602 (7) Å | T = 100 K |
β = 96.954 (1)° | Plate, red |
V = 2499.39 (15) Å3 | 0.25 × 0.15 × 0.05 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 6039 independent reflections |
Radiation source: fine-focus sealed tube | 4998 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
φ and ω scans | θmax = 28.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −19→19 |
Tmin = 0.981, Tmax = 0.996 | k = −10→10 |
24794 measured reflections | l = −28→27 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.108 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0562P)2 + 0.76P] where P = (Fo2 + 2Fc2)/3 |
6039 reflections | (Δ/σ)max < 0.001 |
311 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | −0.00038 (6) | 0.64946 (12) | 0.42442 (4) | 0.0264 (2) | |
N1 | 0.15945 (6) | 0.50058 (13) | 0.29390 (4) | 0.0176 (2) | |
H1 | 0.1734 (10) | 0.609 (2) | 0.2891 (6) | 0.025 (4)* | |
N2 | 0.50399 (7) | 0.36491 (14) | 0.60934 (5) | 0.0265 (2) | |
N3 | −0.34302 (6) | 0.57380 (12) | 0.09261 (4) | 0.0184 (2) | |
C2 | 0.19183 (7) | 0.44718 (14) | 0.35672 (5) | 0.0175 (2) | |
H2A | 0.2550 | 0.4884 | 0.3670 | 0.021* | |
H2B | 0.1932 | 0.3196 | 0.3581 | 0.021* | |
C3 | 0.13620 (7) | 0.51119 (14) | 0.40577 (5) | 0.0165 (2) | |
C4 | 0.04303 (7) | 0.57945 (14) | 0.38662 (5) | 0.0183 (2) | |
C5 | 0.00409 (7) | 0.55836 (14) | 0.32113 (5) | 0.0169 (2) | |
C6 | 0.06224 (7) | 0.47205 (15) | 0.27791 (5) | 0.0180 (2) | |
H6A | 0.0503 | 0.3465 | 0.2778 | 0.022* | |
H6B | 0.0441 | 0.5154 | 0.2356 | 0.022* | |
C7 | 0.16591 (8) | 0.51218 (14) | 0.46674 (5) | 0.0185 (2) | |
H7 | 0.1223 | 0.5510 | 0.4920 | 0.022* | |
C8 | 0.25284 (8) | 0.46434 (14) | 0.50058 (5) | 0.0181 (2) | |
C9 | 0.32269 (8) | 0.37078 (14) | 0.47781 (5) | 0.0193 (2) | |
H9 | 0.3134 | 0.3290 | 0.4367 | 0.023* | |
C10 | 0.40422 (8) | 0.33753 (14) | 0.51311 (5) | 0.0205 (2) | |
H10 | 0.4494 | 0.2736 | 0.4957 | 0.025* | |
C11 | 0.42215 (8) | 0.39629 (15) | 0.57462 (6) | 0.0213 (2) | |
C12 | 0.35142 (9) | 0.48654 (16) | 0.59851 (6) | 0.0243 (3) | |
H12 | 0.3599 | 0.5265 | 0.6399 | 0.029* | |
C13 | 0.27032 (8) | 0.51723 (15) | 0.56236 (6) | 0.0224 (2) | |
H13 | 0.2240 | 0.5770 | 0.5801 | 0.027* | |
C14 | 0.57408 (8) | 0.26334 (15) | 0.58470 (6) | 0.0226 (2) | |
H14A | 0.6334 | 0.2888 | 0.6087 | 0.027* | |
H14B | 0.5776 | 0.2985 | 0.5415 | 0.027* | |
C15 | 0.55674 (8) | 0.07010 (15) | 0.58652 (6) | 0.0228 (2) | |
H15A | 0.6025 | 0.0093 | 0.5660 | 0.034* | |
H15B | 0.4962 | 0.0448 | 0.5653 | 0.034* | |
H15C | 0.5603 | 0.0319 | 0.6295 | 0.034* | |
C16 | 0.52166 (9) | 0.42674 (16) | 0.67271 (6) | 0.0253 (3) | |
H16A | 0.5728 | 0.3604 | 0.6944 | 0.030* | |
H16B | 0.4675 | 0.4043 | 0.6939 | 0.030* | |
C17 | 0.54427 (9) | 0.61812 (17) | 0.67766 (6) | 0.0291 (3) | |
H17A | 0.5521 | 0.6525 | 0.7211 | 0.044* | |
H17B | 0.4947 | 0.6848 | 0.6553 | 0.044* | |
H17C | 0.6005 | 0.6402 | 0.6597 | 0.044* | |
C18 | −0.08113 (8) | 0.61735 (14) | 0.30447 (5) | 0.0185 (2) | |
H18 | −0.1063 | 0.6772 | 0.3363 | 0.022* | |
C19 | −0.14147 (7) | 0.60650 (14) | 0.24708 (5) | 0.0175 (2) | |
C20 | −0.13078 (7) | 0.50118 (14) | 0.19586 (5) | 0.0175 (2) | |
H20 | −0.0774 | 0.4334 | 0.1966 | 0.021* | |
C21 | −0.19492 (7) | 0.49294 (14) | 0.14489 (5) | 0.0176 (2) | |
H21 | −0.1839 | 0.4222 | 0.1111 | 0.021* | |
C22 | −0.27709 (7) | 0.58768 (14) | 0.14170 (5) | 0.0164 (2) | |
C23 | −0.28765 (8) | 0.69586 (15) | 0.19233 (5) | 0.0205 (2) | |
H23 | −0.3408 | 0.7645 | 0.1917 | 0.025* | |
C24 | −0.22217 (8) | 0.70345 (15) | 0.24259 (5) | 0.0214 (2) | |
H24 | −0.2319 | 0.7775 | 0.2758 | 0.026* | |
C25 | −0.33774 (8) | 0.44712 (15) | 0.04373 (5) | 0.0207 (2) | |
H25A | −0.3997 | 0.4074 | 0.0283 | 0.025* | |
H25B | −0.3026 | 0.3460 | 0.0609 | 0.025* | |
C26 | −0.29326 (10) | 0.51986 (18) | −0.00960 (6) | 0.0309 (3) | |
H26A | −0.2912 | 0.4309 | −0.0412 | 0.046* | |
H26B | −0.2314 | 0.5571 | 0.0052 | 0.046* | |
H26C | −0.3284 | 0.6187 | −0.0273 | 0.046* | |
C27 | −0.42747 (7) | 0.67278 (15) | 0.08884 (5) | 0.0200 (2) | |
H27A | −0.4519 | 0.6879 | 0.0450 | 0.024* | |
H27B | −0.4143 | 0.7886 | 0.1067 | 0.024* | |
C28 | −0.49906 (8) | 0.58568 (17) | 0.12264 (7) | 0.0282 (3) | |
H28A | −0.5549 | 0.6542 | 0.1175 | 0.042* | |
H28B | −0.4767 | 0.5767 | 0.1666 | 0.042* | |
H28C | −0.5116 | 0.4701 | 0.1056 | 0.042* | |
O2 | 0.24587 (6) | 0.32664 (11) | 0.21038 (4) | 0.02339 (19) | |
H2 | 0.2172 (11) | 0.381 (2) | 0.2394 (8) | 0.041 (5)* | |
C29 | 0.28729 (9) | 0.45617 (18) | 0.17799 (6) | 0.0295 (3) | |
H29A | 0.2404 | 0.5228 | 0.1529 | 0.044* | |
H29B | 0.3277 | 0.4026 | 0.1512 | 0.044* | |
H29C | 0.3225 | 0.5329 | 0.2074 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0251 (4) | 0.0340 (5) | 0.0201 (4) | 0.0104 (4) | 0.0022 (3) | −0.0049 (4) |
N1 | 0.0173 (5) | 0.0182 (5) | 0.0178 (5) | −0.0008 (4) | 0.0036 (4) | 0.0005 (4) |
N2 | 0.0282 (5) | 0.0225 (5) | 0.0258 (6) | 0.0079 (4) | −0.0086 (4) | −0.0080 (4) |
N3 | 0.0173 (4) | 0.0208 (5) | 0.0172 (5) | 0.0022 (4) | 0.0022 (4) | −0.0030 (4) |
C2 | 0.0163 (5) | 0.0174 (5) | 0.0185 (5) | 0.0007 (4) | 0.0017 (4) | −0.0007 (4) |
C3 | 0.0173 (5) | 0.0136 (5) | 0.0188 (6) | −0.0008 (4) | 0.0022 (4) | −0.0006 (4) |
C4 | 0.0192 (5) | 0.0161 (5) | 0.0197 (6) | 0.0014 (4) | 0.0027 (4) | 0.0000 (4) |
C5 | 0.0195 (5) | 0.0150 (5) | 0.0164 (5) | −0.0009 (4) | 0.0031 (4) | −0.0004 (4) |
C6 | 0.0174 (5) | 0.0202 (5) | 0.0166 (5) | 0.0009 (4) | 0.0022 (4) | −0.0011 (4) |
C7 | 0.0199 (5) | 0.0150 (5) | 0.0206 (6) | 0.0005 (4) | 0.0029 (4) | −0.0019 (4) |
C8 | 0.0205 (5) | 0.0145 (5) | 0.0190 (6) | −0.0006 (4) | 0.0006 (4) | −0.0005 (4) |
C9 | 0.0241 (6) | 0.0161 (5) | 0.0172 (5) | −0.0004 (4) | 0.0009 (4) | −0.0008 (4) |
C10 | 0.0220 (5) | 0.0165 (5) | 0.0230 (6) | 0.0028 (4) | 0.0020 (5) | −0.0017 (4) |
C11 | 0.0249 (6) | 0.0148 (5) | 0.0227 (6) | 0.0017 (4) | −0.0031 (5) | −0.0014 (4) |
C12 | 0.0300 (6) | 0.0216 (6) | 0.0198 (6) | 0.0035 (5) | −0.0026 (5) | −0.0050 (5) |
C13 | 0.0255 (6) | 0.0200 (6) | 0.0217 (6) | 0.0038 (5) | 0.0020 (5) | −0.0042 (5) |
C14 | 0.0198 (5) | 0.0202 (6) | 0.0266 (6) | 0.0005 (4) | −0.0023 (5) | −0.0001 (5) |
C15 | 0.0247 (6) | 0.0197 (6) | 0.0242 (6) | 0.0041 (5) | 0.0037 (5) | −0.0002 (5) |
C16 | 0.0294 (6) | 0.0224 (6) | 0.0216 (6) | 0.0034 (5) | −0.0070 (5) | −0.0014 (5) |
C17 | 0.0289 (6) | 0.0249 (6) | 0.0319 (7) | 0.0005 (5) | −0.0033 (5) | −0.0087 (5) |
C18 | 0.0210 (5) | 0.0171 (5) | 0.0178 (5) | 0.0009 (4) | 0.0041 (4) | −0.0016 (4) |
C19 | 0.0170 (5) | 0.0173 (5) | 0.0185 (6) | 0.0007 (4) | 0.0034 (4) | 0.0004 (4) |
C20 | 0.0158 (5) | 0.0168 (5) | 0.0206 (6) | 0.0023 (4) | 0.0053 (4) | 0.0011 (4) |
C21 | 0.0195 (5) | 0.0171 (5) | 0.0172 (5) | 0.0012 (4) | 0.0062 (4) | −0.0007 (4) |
C22 | 0.0173 (5) | 0.0158 (5) | 0.0164 (5) | −0.0009 (4) | 0.0030 (4) | 0.0019 (4) |
C23 | 0.0181 (5) | 0.0213 (6) | 0.0219 (6) | 0.0057 (4) | 0.0022 (4) | −0.0026 (4) |
C24 | 0.0214 (6) | 0.0221 (6) | 0.0208 (6) | 0.0038 (4) | 0.0026 (4) | −0.0051 (5) |
C25 | 0.0226 (5) | 0.0207 (6) | 0.0184 (6) | 0.0015 (4) | 0.0013 (4) | −0.0038 (4) |
C26 | 0.0444 (8) | 0.0294 (7) | 0.0200 (6) | 0.0103 (6) | 0.0090 (6) | 0.0017 (5) |
C27 | 0.0171 (5) | 0.0209 (6) | 0.0217 (6) | 0.0027 (4) | 0.0008 (4) | −0.0009 (4) |
C28 | 0.0206 (6) | 0.0278 (7) | 0.0379 (7) | 0.0007 (5) | 0.0098 (5) | −0.0019 (5) |
O2 | 0.0279 (4) | 0.0200 (4) | 0.0243 (5) | 0.0013 (3) | 0.0113 (4) | −0.0004 (3) |
C29 | 0.0323 (7) | 0.0321 (7) | 0.0258 (7) | −0.0029 (5) | 0.0101 (5) | 0.0057 (5) |
O1—C4 | 1.2337 (14) | C15—H15C | 0.9800 |
N1—C2 | 1.4590 (14) | C16—C17 | 1.5231 (18) |
N1—C6 | 1.4601 (14) | C16—H16A | 0.9900 |
N1—H1 | 0.878 (15) | C16—H16B | 0.9900 |
N2—C11 | 1.3742 (15) | C17—H17A | 0.9800 |
N2—C14 | 1.4594 (16) | C17—H17B | 0.9800 |
N2—C16 | 1.4594 (16) | C17—H17C | 0.9800 |
N3—C22 | 1.3664 (14) | C18—C19 | 1.4530 (16) |
N3—C25 | 1.4608 (14) | C18—H18 | 0.9500 |
N3—C27 | 1.4641 (14) | C19—C24 | 1.4079 (15) |
C2—C3 | 1.5144 (15) | C19—C20 | 1.4105 (15) |
C2—H2A | 0.9900 | C20—C21 | 1.3769 (16) |
C2—H2B | 0.9900 | C20—H20 | 0.9500 |
C3—C7 | 1.3524 (16) | C21—C22 | 1.4186 (15) |
C3—C4 | 1.4929 (15) | C21—H21 | 0.9500 |
C4—C5 | 1.4867 (16) | C22—C23 | 1.4127 (16) |
C5—C18 | 1.3535 (16) | C23—C24 | 1.3774 (16) |
C5—C6 | 1.5112 (15) | C23—H23 | 0.9500 |
C6—H6A | 0.9900 | C24—H24 | 0.9500 |
C6—H6B | 0.9900 | C25—C26 | 1.5167 (17) |
C7—C8 | 1.4559 (16) | C25—H25A | 0.9900 |
C7—H7 | 0.9500 | C25—H25B | 0.9900 |
C8—C13 | 1.4052 (16) | C26—H26A | 0.9800 |
C8—C9 | 1.4054 (16) | C26—H26B | 0.9800 |
C9—C10 | 1.3789 (16) | C26—H26C | 0.9800 |
C9—H9 | 0.9500 | C27—C28 | 1.5238 (16) |
C10—C11 | 1.4143 (16) | C27—H27A | 0.9900 |
C10—H10 | 0.9500 | C27—H27B | 0.9900 |
C11—C12 | 1.4136 (17) | C28—H28A | 0.9800 |
C12—C13 | 1.3787 (17) | C28—H28B | 0.9800 |
C12—H12 | 0.9500 | C28—H28C | 0.9800 |
C13—H13 | 0.9500 | O2—C29 | 1.4123 (15) |
C14—C15 | 1.5224 (17) | O2—H2 | 0.910 (18) |
C14—H14A | 0.9900 | C29—H29A | 0.9800 |
C14—H14B | 0.9900 | C29—H29B | 0.9800 |
C15—H15A | 0.9800 | C29—H29C | 0.9800 |
C15—H15B | 0.9800 | ||
C2—N1—C6 | 112.69 (9) | N2—C16—H16A | 108.8 |
C2—N1—H1 | 109.3 (9) | C17—C16—H16A | 108.8 |
C6—N1—H1 | 111.0 (9) | N2—C16—H16B | 108.8 |
C11—N2—C14 | 120.94 (10) | C17—C16—H16B | 108.8 |
C11—N2—C16 | 120.75 (10) | H16A—C16—H16B | 107.7 |
C14—N2—C16 | 118.27 (10) | C16—C17—H17A | 109.5 |
C22—N3—C25 | 122.05 (9) | C16—C17—H17B | 109.5 |
C22—N3—C27 | 122.01 (9) | H17A—C17—H17B | 109.5 |
C25—N3—C27 | 115.67 (9) | C16—C17—H17C | 109.5 |
N1—C2—C3 | 115.31 (9) | H17A—C17—H17C | 109.5 |
N1—C2—H2A | 108.4 | H17B—C17—H17C | 109.5 |
C3—C2—H2A | 108.4 | C5—C18—C19 | 132.18 (10) |
N1—C2—H2B | 108.4 | C5—C18—H18 | 113.9 |
C3—C2—H2B | 108.4 | C19—C18—H18 | 113.9 |
H2A—C2—H2B | 107.5 | C24—C19—C20 | 115.52 (10) |
C7—C3—C4 | 117.06 (10) | C24—C19—C18 | 117.37 (10) |
C7—C3—C2 | 123.98 (10) | C20—C19—C18 | 127.01 (10) |
C4—C3—C2 | 118.96 (10) | C21—C20—C19 | 122.41 (10) |
O1—C4—C5 | 121.31 (10) | C21—C20—H20 | 118.8 |
O1—C4—C3 | 120.65 (10) | C19—C20—H20 | 118.8 |
C5—C4—C3 | 118.03 (9) | C20—C21—C22 | 121.47 (10) |
C18—C5—C4 | 117.64 (10) | C20—C21—H21 | 119.3 |
C18—C5—C6 | 124.60 (10) | C22—C21—H21 | 119.3 |
C4—C5—C6 | 117.76 (9) | N3—C22—C23 | 121.68 (10) |
N1—C6—C5 | 113.96 (9) | N3—C22—C21 | 121.85 (10) |
N1—C6—H6A | 108.8 | C23—C22—C21 | 116.47 (10) |
C5—C6—H6A | 108.8 | C24—C23—C22 | 121.04 (10) |
N1—C6—H6B | 108.8 | C24—C23—H23 | 119.5 |
C5—C6—H6B | 108.8 | C22—C23—H23 | 119.5 |
H6A—C6—H6B | 107.7 | C23—C24—C19 | 123.04 (11) |
C3—C7—C8 | 131.50 (11) | C23—C24—H24 | 118.5 |
C3—C7—H7 | 114.3 | C19—C24—H24 | 118.5 |
C8—C7—H7 | 114.3 | N3—C25—C26 | 112.27 (10) |
C13—C8—C9 | 115.65 (10) | N3—C25—H25A | 109.2 |
C13—C8—C7 | 117.59 (10) | C26—C25—H25A | 109.2 |
C9—C8—C7 | 126.76 (10) | N3—C25—H25B | 109.2 |
C10—C9—C8 | 122.27 (11) | C26—C25—H25B | 109.2 |
C10—C9—H9 | 118.9 | H25A—C25—H25B | 107.9 |
C8—C9—H9 | 118.9 | C25—C26—H26A | 109.5 |
C9—C10—C11 | 121.55 (11) | C25—C26—H26B | 109.5 |
C9—C10—H10 | 119.2 | H26A—C26—H26B | 109.5 |
C11—C10—H10 | 119.2 | C25—C26—H26C | 109.5 |
N2—C11—C12 | 122.03 (11) | H26A—C26—H26C | 109.5 |
N2—C11—C10 | 121.34 (11) | H26B—C26—H26C | 109.5 |
C12—C11—C10 | 116.62 (10) | N3—C27—C28 | 112.52 (10) |
C13—C12—C11 | 120.67 (11) | N3—C27—H27A | 109.1 |
C13—C12—H12 | 119.7 | C28—C27—H27A | 109.1 |
C11—C12—H12 | 119.7 | N3—C27—H27B | 109.1 |
C12—C13—C8 | 123.18 (11) | C28—C27—H27B | 109.1 |
C12—C13—H13 | 118.4 | H27A—C27—H27B | 107.8 |
C8—C13—H13 | 118.4 | C27—C28—H28A | 109.5 |
N2—C14—C15 | 113.05 (10) | C27—C28—H28B | 109.5 |
N2—C14—H14A | 109.0 | H28A—C28—H28B | 109.5 |
C15—C14—H14A | 109.0 | C27—C28—H28C | 109.5 |
N2—C14—H14B | 109.0 | H28A—C28—H28C | 109.5 |
C15—C14—H14B | 109.0 | H28B—C28—H28C | 109.5 |
H14A—C14—H14B | 107.8 | C29—O2—H2 | 106.7 (11) |
C14—C15—H15A | 109.5 | O2—C29—H29A | 109.5 |
C14—C15—H15B | 109.5 | O2—C29—H29B | 109.5 |
H15A—C15—H15B | 109.5 | H29A—C29—H29B | 109.5 |
C14—C15—H15C | 109.5 | O2—C29—H29C | 109.5 |
H15A—C15—H15C | 109.5 | H29A—C29—H29C | 109.5 |
H15B—C15—H15C | 109.5 | H29B—C29—H29C | 109.5 |
N2—C16—C17 | 113.61 (11) | ||
C6—N1—C2—C3 | −48.39 (13) | C11—C12—C13—C8 | −0.77 (19) |
N1—C2—C3—C7 | −163.33 (10) | C9—C8—C13—C12 | 2.36 (18) |
N1—C2—C3—C4 | 16.07 (14) | C7—C8—C13—C12 | −177.14 (11) |
C7—C3—C4—O1 | 7.25 (16) | C11—N2—C14—C15 | −78.79 (15) |
C2—C3—C4—O1 | −172.19 (11) | C16—N2—C14—C15 | 98.87 (13) |
C7—C3—C4—C5 | −171.98 (10) | C11—N2—C16—C17 | −77.86 (15) |
C2—C3—C4—C5 | 8.58 (15) | C14—N2—C16—C17 | 104.48 (13) |
O1—C4—C5—C18 | −0.59 (17) | C4—C5—C18—C19 | −174.55 (11) |
C3—C4—C5—C18 | 178.64 (10) | C6—C5—C18—C19 | 5.2 (2) |
O1—C4—C5—C6 | 179.64 (11) | C5—C18—C19—C24 | −171.40 (12) |
C3—C4—C5—C6 | −1.14 (15) | C5—C18—C19—C20 | 12.4 (2) |
C2—N1—C6—C5 | 56.02 (13) | C24—C19—C20—C21 | −0.20 (16) |
C18—C5—C6—N1 | 149.39 (11) | C18—C19—C20—C21 | 176.03 (11) |
C4—C5—C6—N1 | −30.85 (14) | C19—C20—C21—C22 | −1.57 (17) |
C4—C3—C7—C8 | −176.56 (11) | C25—N3—C22—C23 | −172.35 (10) |
C2—C3—C7—C8 | 2.9 (2) | C27—N3—C22—C23 | 1.40 (16) |
C3—C7—C8—C13 | 165.37 (12) | C25—N3—C22—C21 | 6.93 (16) |
C3—C7—C8—C9 | −14.1 (2) | C27—N3—C22—C21 | −179.31 (10) |
C13—C8—C9—C10 | −1.95 (17) | C20—C21—C22—N3 | −176.75 (10) |
C7—C8—C9—C10 | 177.50 (11) | C20—C21—C22—C23 | 2.57 (16) |
C8—C9—C10—C11 | −0.03 (18) | N3—C22—C23—C24 | 177.42 (11) |
C14—N2—C11—C12 | 176.63 (11) | C21—C22—C23—C24 | −1.90 (17) |
C16—N2—C11—C12 | −0.96 (18) | C22—C23—C24—C19 | 0.20 (19) |
C14—N2—C11—C10 | −2.58 (18) | C20—C19—C24—C23 | 0.88 (17) |
C16—N2—C11—C10 | 179.82 (11) | C18—C19—C24—C23 | −175.72 (11) |
C9—C10—C11—N2 | −179.08 (11) | C22—N3—C25—C26 | −92.64 (13) |
C9—C10—C11—C12 | 1.67 (17) | C27—N3—C25—C26 | 93.24 (12) |
N2—C11—C12—C13 | 179.47 (12) | C22—N3—C27—C28 | −84.62 (13) |
C10—C11—C12—C13 | −1.28 (18) | C25—N3—C27—C28 | 89.50 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.878 (15) | 2.068 (15) | 2.9009 (13) | 158.1 (13) |
O2—H2···N1 | 0.910 (18) | 1.806 (18) | 2.7144 (13) | 176.4 (16) |
Symmetry code: (i) −x+1/2, y+1/2, −z+1/2. |
2C27H36N3O+·C4H4O42− | Z = 2 |
Mr = 953.27 | F(000) = 1028 |
Triclinic, P1 | Dx = 1.244 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.1075 (15) Å | Cell parameters from 4344 reflections |
b = 12.9650 (18) Å | θ = 2.2–30.4° |
c = 17.899 (3) Å | µ = 0.08 mm−1 |
α = 96.320 (3)° | T = 100 K |
β = 92.211 (3)° | Prism, yellow |
γ = 95.861 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 2545.3 (7) Å3 |
Bruker APEXII CCD area-detector diffractometer | 9952 independent reflections |
Radiation source: fine-focus sealed tube | 6795 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
φ and ω scans | θmax = 26.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −13→13 |
Tmin = 0.976, Tmax = 0.992 | k = −15→15 |
16330 measured reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.067 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0897P)2 + 1.4P] where P = (Fo2 + 2Fc2)/3 |
9952 reflections | (Δ/σ)max < 0.001 |
647 parameters | Δρmax = 0.56 e Å−3 |
6 restraints | Δρmin = −0.52 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1A | 1.08996 (17) | 0.70377 (16) | 0.87565 (11) | 0.0340 (5) | |
N1A | 0.8329 (2) | 0.65779 (18) | 0.70200 (12) | 0.0292 (5) | |
H1A | 0.7842 | 0.6912 | 0.7335 | 0.035* | |
H1B | 0.7948 | 0.6358 | 0.6549 | 0.035* | |
N2A | 1.2124 (4) | 1.1885 (2) | 0.60754 (14) | 0.0719 (12) | |
N3A | 0.60699 (19) | 0.18989 (18) | 0.94333 (12) | 0.0274 (5) | |
C2A | 0.9450 (2) | 0.7225 (2) | 0.68893 (14) | 0.0283 (6) | |
H2A | 0.9237 | 0.7859 | 0.6675 | 0.034* | |
H2B | 0.9912 | 0.6830 | 0.6514 | 0.034* | |
C3A | 1.0241 (2) | 0.7545 (2) | 0.75943 (15) | 0.0249 (6) | |
C4A | 1.0192 (2) | 0.6846 (2) | 0.81997 (15) | 0.0256 (6) | |
C5A | 0.9263 (2) | 0.5930 (2) | 0.81242 (14) | 0.0241 (6) | |
C6A | 0.8555 (3) | 0.5653 (2) | 0.73858 (15) | 0.0302 (6) | |
H6A | 0.9007 | 0.5194 | 0.7047 | 0.036* | |
H6B | 0.7770 | 0.5260 | 0.7471 | 0.036* | |
C7A | 1.0967 (2) | 0.8454 (2) | 0.77244 (15) | 0.0263 (6) | |
H7A | 1.1371 | 0.8565 | 0.8209 | 0.032* | |
C8A | 1.1246 (2) | 0.9290 (2) | 0.72648 (15) | 0.0270 (6) | |
C9A | 1.1204 (3) | 0.9191 (2) | 0.64753 (17) | 0.0392 (7) | |
H9A | 1.0962 | 0.8526 | 0.6203 | 0.047* | |
C10A | 1.1502 (4) | 1.0027 (3) | 0.60840 (18) | 0.0497 (9) | |
H10A | 1.1459 | 0.9926 | 0.5549 | 0.060* | |
C11A | 1.1873 (3) | 1.1039 (2) | 0.64603 (17) | 0.0428 (8) | |
C12A | 1.1943 (2) | 1.1130 (2) | 0.72471 (16) | 0.0314 (6) | |
H12A | 1.2197 | 1.1789 | 0.7524 | 0.038* | |
C13A | 1.1651 (2) | 1.0283 (2) | 0.76219 (16) | 0.0292 (6) | |
H13A | 1.1727 | 1.0376 | 0.8156 | 0.035* | |
C14A | 1.1806 (3) | 1.1851 (4) | 0.52497 (19) | 0.0368 (11) | 0.631 (6) |
H14A | 1.1583 | 1.2539 | 0.5137 | 0.044* | 0.631 (6) |
H14B | 1.1103 | 1.1324 | 0.5104 | 0.044* | 0.631 (6) |
C15A | 1.2895 (4) | 1.1568 (4) | 0.4801 (2) | 0.0472 (13) | 0.631 (6) |
H15A | 1.2669 | 1.1492 | 0.4262 | 0.071* | 0.631 (6) |
H15B | 1.3148 | 1.0909 | 0.4940 | 0.071* | 0.631 (6) |
H15C | 1.3566 | 1.2122 | 0.4915 | 0.071* | 0.631 (6) |
C14C | 1.2712 (5) | 1.1664 (6) | 0.5353 (2) | 0.0368 (11) | 0.37 |
H14E | 1.3034 | 1.0977 | 0.5332 | 0.044* | 0.369 (6) |
H14F | 1.3398 | 1.2204 | 0.5315 | 0.044* | 0.369 (6) |
C15C | 1.1780 (7) | 1.1659 (8) | 0.4696 (2) | 0.0472 (13) | 0.37 |
H15G | 1.2152 | 1.1468 | 0.4220 | 0.071* | 0.369 (6) |
H15H | 1.1510 | 1.2355 | 0.4696 | 0.071* | 0.369 (6) |
H15I | 1.1083 | 1.1151 | 0.4752 | 0.071* | 0.369 (6) |
C16A | 1.2574 (3) | 1.2909 (2) | 0.64667 (18) | 0.0423 (8) | |
H16A | 1.2104 | 1.3038 | 0.6920 | 0.051* | |
H16B | 1.2418 | 1.3447 | 0.6134 | 0.051* | |
C17A | 1.3906 (3) | 1.3044 (3) | 0.6704 (2) | 0.0558 (10) | |
H17A | 1.4121 | 1.3743 | 0.6974 | 0.084* | |
H17B | 1.4386 | 1.2961 | 0.6258 | 0.084* | |
H17C | 1.4075 | 1.2517 | 0.7036 | 0.084* | |
C18A | 0.9078 (2) | 0.5437 (2) | 0.87439 (15) | 0.0273 (6) | |
H18A | 0.9572 | 0.5737 | 0.9174 | 0.033* | |
C19A | 0.8261 (2) | 0.4532 (2) | 0.88704 (14) | 0.0261 (6) | |
C20A | 0.7762 (2) | 0.3734 (2) | 0.83172 (15) | 0.0294 (6) | |
H20A | 0.7931 | 0.3785 | 0.7805 | 0.035* | |
C21A | 0.7038 (2) | 0.2881 (2) | 0.84951 (15) | 0.0292 (6) | |
H21A | 0.6724 | 0.2356 | 0.8104 | 0.035* | |
C22A | 0.6751 (2) | 0.2763 (2) | 0.92421 (15) | 0.0247 (6) | |
C23A | 0.7251 (2) | 0.3564 (2) | 0.98010 (15) | 0.0249 (6) | |
H23A | 0.7077 | 0.3521 | 1.0313 | 0.030* | |
C24A | 0.7982 (2) | 0.4401 (2) | 0.96141 (14) | 0.0245 (6) | |
H24A | 0.8317 | 0.4916 | 1.0006 | 0.029* | |
C25A | 0.5669 (2) | 0.1008 (2) | 0.88766 (16) | 0.0305 (6) | |
H25A | 0.5560 | 0.0370 | 0.9135 | 0.037* | |
H25B | 0.6310 | 0.0916 | 0.8513 | 0.037* | |
C26A | 0.4494 (3) | 0.1125 (3) | 0.84498 (17) | 0.0391 (7) | |
H26A | 0.4250 | 0.0490 | 0.8106 | 0.059* | |
H26B | 0.4613 | 0.1723 | 0.8160 | 0.059* | |
H26C | 0.3861 | 0.1238 | 0.8807 | 0.059* | |
C27A | 0.5607 (2) | 0.1861 (2) | 1.01812 (15) | 0.0269 (6) | |
H27A | 0.4814 | 0.1430 | 1.0137 | 0.032* | |
H27B | 0.5472 | 0.2576 | 1.0392 | 0.032* | |
C28A | 0.6443 (2) | 0.1420 (2) | 1.07231 (16) | 0.0308 (6) | |
H28A | 0.6063 | 0.1388 | 1.1206 | 0.046* | |
H28B | 0.7212 | 0.1870 | 1.0799 | 0.046* | |
H28C | 0.6595 | 0.0717 | 1.0515 | 0.046* | |
O2A | 0.74229 (17) | 0.58814 (18) | 0.57166 (11) | 0.0394 (5) | |
O3A | 0.57358 (18) | 0.5652 (2) | 0.63151 (11) | 0.0486 (6) | |
C29A | 0.6289 (2) | 0.5587 (2) | 0.57354 (14) | 0.0268 (6) | |
C30A | 0.5680 (2) | 0.5105 (2) | 0.49952 (15) | 0.0305 (6) | |
H30A | 0.6015 | 0.4438 | 0.4845 | 0.037* | |
H30B | 0.5882 | 0.5575 | 0.4608 | 0.037* | |
O1B | 0.36751 (17) | 0.34005 (17) | 0.15765 (12) | 0.0404 (5) | |
N1B | 0.63635 (19) | 0.35149 (17) | 0.31356 (11) | 0.0240 (5) | |
H1C | 0.5822 | 0.3891 | 0.3372 | 0.029* | |
H1D | 0.7004 | 0.3539 | 0.3494 | 0.029* | |
N2B | 0.2396 (2) | −0.16004 (19) | 0.40590 (14) | 0.0355 (6) | |
N3B | 0.90546 (19) | 0.76950 (18) | 0.02450 (13) | 0.0298 (5) | |
C2B | 0.5783 (2) | 0.2450 (2) | 0.29200 (15) | 0.0268 (6) | |
H2C | 0.5531 | 0.2140 | 0.3378 | 0.032* | |
H2D | 0.6378 | 0.2020 | 0.2677 | 0.032* | |
C3B | 0.4693 (2) | 0.2427 (2) | 0.23874 (14) | 0.0238 (6) | |
C4B | 0.4620 (2) | 0.3319 (2) | 0.19360 (15) | 0.0266 (6) | |
C5B | 0.5710 (2) | 0.4086 (2) | 0.19306 (14) | 0.0233 (5) | |
C6B | 0.6763 (2) | 0.4015 (2) | 0.24740 (14) | 0.0245 (6) | |
H6C | 0.7363 | 0.3607 | 0.2215 | 0.029* | |
H6D | 0.7164 | 0.4725 | 0.2641 | 0.029* | |
C7B | 0.3743 (2) | 0.1687 (2) | 0.23265 (14) | 0.0230 (5) | |
H7B | 0.3138 | 0.1771 | 0.1954 | 0.028* | |
C8B | 0.3476 (2) | 0.0785 (2) | 0.27265 (14) | 0.0245 (6) | |
C9B | 0.4326 (2) | 0.0286 (2) | 0.31196 (15) | 0.0269 (6) | |
H9B | 0.5165 | 0.0509 | 0.3100 | 0.032* | |
C10B | 0.3976 (2) | −0.0510 (2) | 0.35273 (16) | 0.0291 (6) | |
H10B | 0.4580 | −0.0839 | 0.3773 | 0.035* | |
C11B | 0.2739 (2) | −0.0864 (2) | 0.35979 (15) | 0.0291 (6) | |
C12B | 0.1891 (2) | −0.0404 (2) | 0.31694 (15) | 0.0300 (6) | |
H12B | 0.1053 | −0.0640 | 0.3173 | 0.036* | |
C13B | 0.2259 (2) | 0.0378 (2) | 0.27498 (15) | 0.0262 (6) | |
H13B | 0.1664 | 0.0659 | 0.2460 | 0.031* | |
C14B | 0.3279 (3) | −0.2195 (3) | 0.43982 (19) | 0.0419 (8) | |
H14C | 0.3933 | −0.2303 | 0.4046 | 0.050* | |
H14D | 0.2877 | −0.2889 | 0.4476 | 0.050* | |
C15B | 0.3832 (3) | −0.1653 (3) | 0.51439 (19) | 0.0540 (10) | |
H15D | 0.4439 | −0.2067 | 0.5338 | 0.081* | |
H15E | 0.3195 | −0.1582 | 0.5505 | 0.081* | |
H15F | 0.4219 | −0.0960 | 0.5072 | 0.081* | |
C16B | 0.1130 (3) | −0.1993 (2) | 0.41177 (16) | 0.0341 (7) | |
H16C | 0.0623 | −0.1409 | 0.4101 | 0.041* | |
H16D | 0.1031 | −0.2267 | 0.4609 | 0.041* | |
C17B | 0.0692 (3) | −0.2850 (3) | 0.34902 (18) | 0.0462 (8) | |
H17D | −0.0125 | −0.3151 | 0.3587 | 0.069* | |
H17E | 0.1244 | −0.3395 | 0.3470 | 0.069* | |
H17F | 0.0675 | −0.2556 | 0.3009 | 0.069* | |
C18B | 0.5682 (2) | 0.4784 (2) | 0.14258 (14) | 0.0241 (6) | |
H18B | 0.4918 | 0.4757 | 0.1162 | 0.029* | |
C19B | 0.6584 (2) | 0.5569 (2) | 0.12043 (14) | 0.0232 (5) | |
C20B | 0.7802 (2) | 0.5779 (2) | 0.14715 (14) | 0.0242 (6) | |
H20B | 0.8086 | 0.5409 | 0.1861 | 0.029* | |
C21B | 0.8595 (2) | 0.6505 (2) | 0.11854 (14) | 0.0246 (6) | |
H21B | 0.9400 | 0.6647 | 0.1399 | 0.029* | |
C22B | 0.8243 (2) | 0.7046 (2) | 0.05833 (15) | 0.0257 (6) | |
C23B | 0.7015 (2) | 0.6851 (2) | 0.03169 (16) | 0.0273 (6) | |
H23B | 0.6731 | 0.7211 | −0.0078 | 0.033* | |
C24B | 0.6229 (2) | 0.6140 (2) | 0.06267 (15) | 0.0260 (6) | |
H24B | 0.5408 | 0.6032 | 0.0440 | 0.031* | |
C25B | 1.0324 (2) | 0.7902 (2) | 0.05277 (16) | 0.0289 (6) | |
H25C | 1.0822 | 0.8134 | 0.0118 | 0.035* | |
H25D | 1.0603 | 0.7241 | 0.0661 | 0.035* | |
C26B | 1.0547 (3) | 0.8715 (2) | 0.12062 (17) | 0.0361 (7) | |
H26D | 1.1415 | 0.8824 | 0.1349 | 0.054* | |
H26E | 1.0098 | 0.8475 | 0.1626 | 0.054* | |
H26F | 1.0271 | 0.9373 | 0.1082 | 0.054* | |
C27B | 0.8677 (2) | 0.8222 (2) | −0.03969 (16) | 0.0308 (6) | |
H27C | 0.8102 | 0.7733 | −0.0735 | 0.037* | |
H27D | 0.9395 | 0.8411 | −0.0684 | 0.037* | |
C28B | 0.8084 (3) | 0.9193 (2) | −0.01591 (19) | 0.0406 (8) | |
H28D | 0.7796 | 0.9486 | −0.0607 | 0.061* | |
H28E | 0.8673 | 0.9708 | 0.0136 | 0.061* | |
H28F | 0.7396 | 0.9017 | 0.0148 | 0.061* | |
O2B | 0.80151 (16) | 0.35015 (15) | 0.41720 (10) | 0.0305 (4) | |
O3B | 0.87862 (18) | 0.49971 (16) | 0.38002 (11) | 0.0380 (5) | |
C29B | 0.8752 (2) | 0.4360 (2) | 0.42502 (14) | 0.0241 (6) | |
C30B | 0.9598 (2) | 0.4489 (2) | 0.49504 (15) | 0.0254 (6) | |
H30C | 0.9107 | 0.4443 | 0.5398 | 0.030* | |
H30D | 1.0112 | 0.3908 | 0.4921 | 0.030* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0239 (10) | 0.0401 (12) | 0.0363 (11) | −0.0053 (9) | −0.0094 (8) | 0.0088 (9) |
N1A | 0.0239 (12) | 0.0356 (13) | 0.0258 (12) | 0.0019 (10) | −0.0065 (9) | −0.0034 (10) |
N2A | 0.147 (3) | 0.0305 (16) | 0.0324 (15) | −0.0212 (19) | 0.0272 (18) | −0.0022 (12) |
N3A | 0.0221 (11) | 0.0302 (13) | 0.0273 (12) | −0.0036 (10) | −0.0024 (9) | −0.0007 (10) |
C2A | 0.0315 (15) | 0.0276 (15) | 0.0240 (13) | 0.0000 (12) | −0.0023 (11) | −0.0005 (11) |
C3A | 0.0152 (12) | 0.0293 (15) | 0.0291 (14) | 0.0030 (11) | −0.0009 (10) | −0.0007 (11) |
C4A | 0.0151 (12) | 0.0312 (15) | 0.0300 (14) | 0.0037 (11) | −0.0017 (11) | 0.0005 (12) |
C5A | 0.0191 (12) | 0.0274 (14) | 0.0250 (13) | 0.0032 (11) | −0.0022 (10) | 0.0002 (11) |
C6A | 0.0284 (14) | 0.0316 (15) | 0.0286 (14) | −0.0030 (12) | −0.0049 (11) | 0.0026 (12) |
C7A | 0.0162 (12) | 0.0330 (15) | 0.0293 (14) | 0.0049 (11) | −0.0023 (10) | 0.0007 (12) |
C8A | 0.0189 (13) | 0.0286 (15) | 0.0332 (15) | 0.0023 (11) | 0.0022 (11) | 0.0018 (12) |
C9A | 0.0531 (19) | 0.0292 (16) | 0.0331 (16) | −0.0003 (14) | 0.0115 (14) | −0.0055 (13) |
C10A | 0.081 (3) | 0.0347 (18) | 0.0303 (16) | −0.0048 (17) | 0.0196 (17) | −0.0047 (14) |
C11A | 0.064 (2) | 0.0258 (16) | 0.0375 (17) | −0.0021 (15) | 0.0169 (15) | −0.0015 (13) |
C12A | 0.0294 (15) | 0.0287 (15) | 0.0344 (15) | −0.0004 (12) | 0.0040 (12) | −0.0015 (12) |
C13A | 0.0197 (13) | 0.0369 (16) | 0.0300 (14) | 0.0024 (12) | 0.0000 (11) | 0.0009 (12) |
C14A | 0.034 (2) | 0.027 (2) | 0.053 (3) | 0.0108 (19) | 0.011 (2) | 0.009 (2) |
C15A | 0.040 (2) | 0.048 (3) | 0.054 (3) | 0.008 (2) | 0.011 (2) | 0.003 (2) |
C14C | 0.034 (2) | 0.027 (2) | 0.053 (3) | 0.0108 (19) | 0.011 (2) | 0.009 (2) |
C15C | 0.040 (2) | 0.048 (3) | 0.054 (3) | 0.008 (2) | 0.011 (2) | 0.003 (2) |
C16A | 0.062 (2) | 0.0228 (15) | 0.0422 (18) | 0.0020 (15) | 0.0106 (16) | 0.0026 (13) |
C17A | 0.053 (2) | 0.051 (2) | 0.071 (2) | 0.0193 (18) | 0.0223 (19) | 0.0219 (19) |
C18A | 0.0182 (12) | 0.0329 (15) | 0.0297 (14) | 0.0040 (11) | −0.0021 (11) | −0.0006 (12) |
C19A | 0.0223 (13) | 0.0297 (15) | 0.0260 (13) | 0.0039 (11) | −0.0022 (11) | 0.0025 (11) |
C20A | 0.0295 (14) | 0.0328 (16) | 0.0250 (14) | 0.0024 (12) | 0.0020 (11) | 0.0006 (12) |
C21A | 0.0255 (14) | 0.0316 (15) | 0.0280 (14) | −0.0009 (12) | −0.0026 (11) | −0.0029 (12) |
C22A | 0.0167 (12) | 0.0266 (14) | 0.0303 (14) | 0.0023 (11) | −0.0023 (10) | 0.0019 (11) |
C23A | 0.0195 (12) | 0.0290 (15) | 0.0260 (13) | 0.0041 (11) | −0.0002 (10) | 0.0014 (11) |
C24A | 0.0214 (13) | 0.0252 (14) | 0.0261 (13) | 0.0043 (11) | −0.0018 (10) | −0.0019 (11) |
C25A | 0.0260 (14) | 0.0302 (15) | 0.0322 (15) | −0.0033 (12) | −0.0004 (11) | −0.0033 (12) |
C26A | 0.0244 (15) | 0.054 (2) | 0.0343 (16) | −0.0041 (14) | −0.0064 (12) | −0.0033 (14) |
C27A | 0.0177 (12) | 0.0297 (15) | 0.0323 (14) | −0.0005 (11) | 0.0001 (11) | 0.0024 (12) |
C28A | 0.0267 (14) | 0.0331 (16) | 0.0317 (15) | −0.0003 (12) | −0.0032 (12) | 0.0041 (12) |
O2A | 0.0222 (10) | 0.0596 (14) | 0.0315 (11) | −0.0077 (10) | −0.0046 (8) | −0.0029 (10) |
O3A | 0.0278 (11) | 0.0831 (18) | 0.0288 (11) | 0.0009 (11) | −0.0009 (9) | −0.0151 (11) |
C29A | 0.0248 (14) | 0.0300 (15) | 0.0246 (14) | 0.0019 (11) | −0.0025 (11) | 0.0002 (11) |
C30A | 0.0248 (14) | 0.0415 (17) | 0.0226 (13) | −0.0006 (12) | −0.0020 (11) | −0.0024 (12) |
O1B | 0.0233 (10) | 0.0426 (13) | 0.0546 (13) | −0.0082 (9) | −0.0168 (9) | 0.0191 (10) |
N1B | 0.0180 (10) | 0.0314 (12) | 0.0204 (11) | −0.0035 (9) | −0.0046 (8) | 0.0014 (9) |
N2B | 0.0313 (13) | 0.0332 (14) | 0.0426 (14) | −0.0010 (11) | 0.0008 (11) | 0.0116 (11) |
N3B | 0.0183 (11) | 0.0329 (13) | 0.0390 (13) | −0.0006 (10) | −0.0024 (10) | 0.0122 (11) |
C2B | 0.0239 (13) | 0.0274 (14) | 0.0280 (14) | −0.0030 (11) | −0.0040 (11) | 0.0053 (11) |
C3B | 0.0195 (12) | 0.0292 (14) | 0.0219 (13) | 0.0012 (11) | 0.0012 (10) | 0.0011 (11) |
C4B | 0.0198 (13) | 0.0316 (15) | 0.0269 (14) | 0.0001 (11) | −0.0009 (11) | 0.0008 (11) |
C5B | 0.0182 (12) | 0.0264 (14) | 0.0243 (13) | 0.0001 (11) | −0.0007 (10) | 0.0012 (11) |
C6B | 0.0182 (12) | 0.0310 (15) | 0.0231 (13) | −0.0018 (11) | −0.0017 (10) | 0.0030 (11) |
C7B | 0.0196 (12) | 0.0278 (14) | 0.0202 (12) | 0.0024 (11) | 0.0000 (10) | −0.0034 (10) |
C8B | 0.0242 (13) | 0.0263 (14) | 0.0201 (12) | −0.0037 (11) | −0.0003 (10) | −0.0032 (10) |
C9B | 0.0212 (13) | 0.0301 (15) | 0.0279 (14) | 0.0007 (11) | 0.0004 (11) | −0.0008 (11) |
C10B | 0.0254 (14) | 0.0266 (15) | 0.0348 (15) | 0.0040 (12) | −0.0006 (12) | 0.0012 (12) |
C11B | 0.0301 (15) | 0.0262 (14) | 0.0295 (14) | −0.0018 (12) | −0.0012 (11) | 0.0018 (11) |
C12B | 0.0238 (14) | 0.0313 (15) | 0.0319 (15) | −0.0073 (12) | −0.0041 (11) | 0.0012 (12) |
C13B | 0.0254 (14) | 0.0239 (14) | 0.0274 (14) | 0.0006 (11) | −0.0039 (11) | −0.0017 (11) |
C14B | 0.0388 (17) | 0.0380 (18) | 0.054 (2) | 0.0086 (14) | 0.0091 (15) | 0.0212 (15) |
C15B | 0.0351 (18) | 0.084 (3) | 0.049 (2) | 0.0098 (18) | 0.0050 (15) | 0.0279 (19) |
C16B | 0.0328 (15) | 0.0320 (16) | 0.0374 (16) | −0.0021 (13) | 0.0052 (13) | 0.0075 (13) |
C17B | 0.054 (2) | 0.0392 (19) | 0.0419 (18) | −0.0129 (16) | 0.0023 (15) | 0.0069 (15) |
C18B | 0.0158 (12) | 0.0288 (14) | 0.0259 (13) | 0.0010 (11) | −0.0031 (10) | −0.0019 (11) |
C19B | 0.0212 (13) | 0.0224 (13) | 0.0252 (13) | 0.0028 (11) | 0.0005 (10) | −0.0002 (10) |
C20B | 0.0210 (13) | 0.0286 (14) | 0.0221 (13) | 0.0020 (11) | −0.0015 (10) | 0.0005 (11) |
C21B | 0.0184 (12) | 0.0277 (14) | 0.0266 (13) | 0.0020 (11) | −0.0010 (10) | −0.0003 (11) |
C22B | 0.0208 (13) | 0.0256 (14) | 0.0305 (14) | 0.0023 (11) | 0.0010 (11) | 0.0023 (11) |
C23B | 0.0202 (13) | 0.0259 (14) | 0.0367 (15) | 0.0028 (11) | −0.0042 (11) | 0.0099 (12) |
C24B | 0.0162 (12) | 0.0288 (15) | 0.0330 (14) | 0.0033 (11) | −0.0043 (11) | 0.0046 (12) |
C25B | 0.0180 (13) | 0.0324 (15) | 0.0362 (15) | −0.0014 (11) | −0.0002 (11) | 0.0076 (12) |
C26B | 0.0290 (15) | 0.0345 (17) | 0.0433 (17) | −0.0002 (13) | 0.0022 (13) | 0.0007 (13) |
C27B | 0.0236 (14) | 0.0341 (16) | 0.0352 (15) | 0.0008 (12) | 0.0027 (12) | 0.0071 (13) |
C28B | 0.0295 (16) | 0.0354 (17) | 0.058 (2) | 0.0028 (13) | 0.0056 (14) | 0.0123 (15) |
O2B | 0.0264 (10) | 0.0300 (11) | 0.0328 (10) | −0.0068 (8) | −0.0099 (8) | 0.0065 (8) |
O3B | 0.0379 (12) | 0.0343 (12) | 0.0389 (12) | −0.0103 (9) | −0.0150 (9) | 0.0113 (9) |
C29B | 0.0177 (12) | 0.0269 (14) | 0.0271 (14) | −0.0003 (11) | −0.0013 (10) | 0.0038 (11) |
C30B | 0.0219 (13) | 0.0256 (14) | 0.0275 (14) | −0.0010 (11) | −0.0053 (11) | 0.0034 (11) |
O1A—C4A | 1.232 (3) | C30A—C30Ai | 1.508 (5) |
N1A—C6A | 1.466 (4) | C30A—H30A | 0.9900 |
N1A—C2A | 1.470 (3) | C30A—H30B | 0.9900 |
N1A—H1A | 0.9030 | O1B—C4B | 1.230 (3) |
N1A—H1B | 0.9300 | N1B—C2B | 1.466 (3) |
N2A—C11A | 1.369 (4) | N1B—C6B | 1.473 (3) |
N2A—C16A | 1.462 (4) | N1B—H1C | 0.9010 |
N2A—C14C | 1.485 (3) | N1B—H1D | 0.9361 |
N2A—C14A | 1.501 (3) | N2B—C11B | 1.364 (4) |
N3A—C22A | 1.370 (3) | N2B—C16B | 1.457 (4) |
N3A—C27A | 1.456 (3) | N2B—C14B | 1.461 (4) |
N3A—C25A | 1.461 (3) | N3B—C22B | 1.373 (3) |
C2A—C3A | 1.504 (4) | N3B—C25B | 1.468 (3) |
C2A—H2A | 0.9900 | N3B—C27B | 1.469 (3) |
C2A—H2B | 0.9900 | C2B—C3B | 1.508 (4) |
C3A—C7A | 1.351 (4) | C2B—H2C | 0.9900 |
C3A—C4A | 1.487 (4) | C2B—H2D | 0.9900 |
C4A—C5A | 1.482 (4) | C3B—C7B | 1.344 (4) |
C5A—C18A | 1.352 (4) | C3B—C4B | 1.488 (4) |
C5A—C6A | 1.501 (4) | C4B—C5B | 1.487 (3) |
C6A—H6A | 0.9900 | C5B—C18B | 1.350 (4) |
C6A—H6B | 0.9900 | C5B—C6B | 1.509 (3) |
C7A—C8A | 1.447 (4) | C6B—H6C | 0.9900 |
C7A—H7A | 0.9500 | C6B—H6D | 0.9900 |
C8A—C13A | 1.395 (4) | C7B—C8B | 1.449 (4) |
C8A—C9A | 1.403 (4) | C7B—H7B | 0.9500 |
C9A—C10A | 1.374 (4) | C8B—C13B | 1.404 (4) |
C9A—H9A | 0.9500 | C8B—C9B | 1.407 (4) |
C10A—C11A | 1.421 (4) | C9B—C10B | 1.362 (4) |
C10A—H10A | 0.9500 | C9B—H9B | 0.9500 |
C11A—C12A | 1.399 (4) | C10B—C11B | 1.418 (4) |
C12A—C13A | 1.367 (4) | C10B—H10B | 0.9500 |
C12A—H12A | 0.9500 | C11B—C12B | 1.411 (4) |
C13A—H13A | 0.9500 | C12B—C13B | 1.365 (4) |
C14A—C15A | 1.530 (3) | C12B—H12B | 0.9500 |
C14A—H14A | 0.9900 | C13B—H13B | 0.9500 |
C14A—H14B | 0.9900 | C14B—C15B | 1.515 (5) |
C15A—H15A | 0.9800 | C14B—H14C | 0.9900 |
C15A—H15B | 0.9800 | C14B—H14D | 0.9900 |
C15A—H15C | 0.9800 | C15B—H15D | 0.9800 |
C14C—C15C | 1.536 (3) | C15B—H15E | 0.9800 |
C14C—H14E | 0.9900 | C15B—H15F | 0.9800 |
C14C—H14F | 0.9900 | C16B—C17B | 1.519 (4) |
C15C—H15G | 0.9800 | C16B—H16C | 0.9900 |
C15C—H15H | 0.9800 | C16B—H16D | 0.9900 |
C15C—H15I | 0.9800 | C17B—H17D | 0.9800 |
C16A—C17A | 1.510 (5) | C17B—H17E | 0.9800 |
C16A—H16A | 0.9900 | C17B—H17F | 0.9800 |
C16A—H16B | 0.9900 | C18B—C19B | 1.451 (3) |
C17A—H17A | 0.9800 | C18B—H18B | 0.9500 |
C17A—H17B | 0.9800 | C19B—C24B | 1.404 (4) |
C17A—H17C | 0.9800 | C19B—C20B | 1.407 (3) |
C18A—C19A | 1.453 (4) | C20B—C21B | 1.377 (4) |
C18A—H18A | 0.9500 | C20B—H20B | 0.9500 |
C19A—C24A | 1.403 (4) | C21B—C22B | 1.413 (4) |
C19A—C20A | 1.405 (4) | C21B—H21B | 0.9500 |
C20A—C21A | 1.374 (4) | C22B—C23B | 1.416 (4) |
C20A—H20A | 0.9500 | C23B—C24B | 1.380 (4) |
C21A—C22A | 1.407 (4) | C23B—H23B | 0.9500 |
C21A—H21A | 0.9500 | C24B—H24B | 0.9500 |
C22A—C23A | 1.414 (4) | C25B—C26B | 1.513 (4) |
C23A—C24A | 1.367 (4) | C25B—H25C | 0.9900 |
C23A—H23A | 0.9500 | C25B—H25D | 0.9900 |
C24A—H24A | 0.9500 | C26B—H26D | 0.9800 |
C25A—C26A | 1.516 (4) | C26B—H26E | 0.9800 |
C25A—H25A | 0.9900 | C26B—H26F | 0.9800 |
C25A—H25B | 0.9900 | C27B—C28B | 1.508 (4) |
C26A—H26A | 0.9800 | C27B—H27C | 0.9900 |
C26A—H26B | 0.9800 | C27B—H27D | 0.9900 |
C26A—H26C | 0.9800 | C28B—H28D | 0.9800 |
C27A—C28A | 1.513 (4) | C28B—H28E | 0.9800 |
C27A—H27A | 0.9900 | C28B—H28F | 0.9800 |
C27A—H27B | 0.9900 | O2B—C29B | 1.304 (3) |
C28A—H28A | 0.9800 | O3B—C29B | 1.214 (3) |
C28A—H28B | 0.9800 | C29B—C30B | 1.521 (4) |
C28A—H28C | 0.9800 | C30B—C30Bii | 1.510 (5) |
O2A—C29A | 1.281 (3) | C30B—H30C | 0.9900 |
O3A—C29A | 1.226 (3) | C30B—H30D | 0.9900 |
C29A—C30A | 1.505 (4) | ||
C6A—N1A—C2A | 112.8 (2) | C30Ai—C30A—H30A | 108.7 |
C6A—N1A—H1A | 103.7 | C29A—C30A—H30B | 108.7 |
C2A—N1A—H1A | 113.2 | C30Ai—C30A—H30B | 108.7 |
C6A—N1A—H1B | 108.5 | H30A—C30A—H30B | 107.6 |
C2A—N1A—H1B | 106.5 | C2B—N1B—C6B | 111.6 (2) |
H1A—N1A—H1B | 112.2 | C2B—N1B—H1C | 108.3 |
C11A—N2A—C16A | 121.4 (3) | C6B—N1B—H1C | 109.1 |
C11A—N2A—C14C | 115.0 (4) | C2B—N1B—H1D | 112.4 |
C16A—N2A—C14C | 112.1 (4) | C6B—N1B—H1D | 110.9 |
C11A—N2A—C14A | 122.1 (3) | H1C—N1B—H1D | 104.2 |
C16A—N2A—C14A | 116.0 (3) | C11B—N2B—C16B | 122.0 (2) |
C22A—N3A—C27A | 121.8 (2) | C11B—N2B—C14B | 121.4 (2) |
C22A—N3A—C25A | 121.6 (2) | C16B—N2B—C14B | 115.3 (2) |
C27A—N3A—C25A | 116.3 (2) | C22B—N3B—C25B | 120.8 (2) |
N1A—C2A—C3A | 112.9 (2) | C22B—N3B—C27B | 121.3 (2) |
N1A—C2A—H2A | 109.0 | C25B—N3B—C27B | 117.9 (2) |
C3A—C2A—H2A | 109.0 | N1B—C2B—C3B | 112.0 (2) |
N1A—C2A—H2B | 109.0 | N1B—C2B—H2C | 109.2 |
C3A—C2A—H2B | 109.0 | C3B—C2B—H2C | 109.2 |
H2A—C2A—H2B | 107.8 | N1B—C2B—H2D | 109.2 |
C7A—C3A—C4A | 117.6 (2) | C3B—C2B—H2D | 109.2 |
C7A—C3A—C2A | 123.8 (2) | H2C—C2B—H2D | 107.9 |
C4A—C3A—C2A | 118.6 (2) | C7B—C3B—C4B | 117.5 (2) |
O1A—C4A—C5A | 121.1 (2) | C7B—C3B—C2B | 124.4 (2) |
O1A—C4A—C3A | 120.3 (2) | C4B—C3B—C2B | 118.0 (2) |
C5A—C4A—C3A | 118.6 (2) | O1B—C4B—C5B | 121.8 (2) |
C18A—C5A—C4A | 116.9 (2) | O1B—C4B—C3B | 119.7 (2) |
C18A—C5A—C6A | 124.9 (2) | C5B—C4B—C3B | 118.4 (2) |
C4A—C5A—C6A | 118.1 (2) | C18B—C5B—C4B | 116.8 (2) |
N1A—C6A—C5A | 112.3 (2) | C18B—C5B—C6B | 125.1 (2) |
N1A—C6A—H6A | 109.1 | C4B—C5B—C6B | 118.1 (2) |
C5A—C6A—H6A | 109.1 | N1B—C6B—C5B | 111.4 (2) |
N1A—C6A—H6B | 109.1 | N1B—C6B—H6C | 109.4 |
C5A—C6A—H6B | 109.1 | C5B—C6B—H6C | 109.4 |
H6A—C6A—H6B | 107.9 | N1B—C6B—H6D | 109.4 |
C3A—C7A—C8A | 132.1 (3) | C5B—C6B—H6D | 109.4 |
C3A—C7A—H7A | 113.9 | H6C—C6B—H6D | 108.0 |
C8A—C7A—H7A | 113.9 | C3B—C7B—C8B | 131.5 (2) |
C13A—C8A—C9A | 115.5 (3) | C3B—C7B—H7B | 114.2 |
C13A—C8A—C7A | 118.6 (2) | C8B—C7B—H7B | 114.2 |
C9A—C8A—C7A | 125.9 (3) | C13B—C8B—C9B | 116.0 (2) |
C10A—C9A—C8A | 121.9 (3) | C13B—C8B—C7B | 118.0 (2) |
C10A—C9A—H9A | 119.0 | C9B—C8B—C7B | 126.0 (2) |
C8A—C9A—H9A | 119.0 | C10B—C9B—C8B | 121.6 (2) |
C9A—C10A—C11A | 121.5 (3) | C10B—C9B—H9B | 119.2 |
C9A—C10A—H10A | 119.2 | C8B—C9B—H9B | 119.2 |
C11A—C10A—H10A | 119.2 | C9B—C10B—C11B | 122.2 (3) |
N2A—C11A—C12A | 121.6 (3) | C9B—C10B—H10B | 118.9 |
N2A—C11A—C10A | 121.9 (3) | C11B—C10B—H10B | 118.9 |
C12A—C11A—C10A | 116.4 (3) | N2B—C11B—C12B | 122.3 (2) |
C13A—C12A—C11A | 120.8 (3) | N2B—C11B—C10B | 121.6 (3) |
C13A—C12A—H12A | 119.6 | C12B—C11B—C10B | 116.1 (2) |
C11A—C12A—H12A | 119.6 | C13B—C12B—C11B | 120.8 (2) |
C12A—C13A—C8A | 123.8 (3) | C13B—C12B—H12B | 119.6 |
C12A—C13A—H13A | 118.1 | C11B—C12B—H12B | 119.6 |
C8A—C13A—H13A | 118.1 | C12B—C13B—C8B | 123.1 (3) |
N2A—C14A—C15A | 109.4 (2) | C12B—C13B—H13B | 118.5 |
N2A—C14A—H14A | 109.8 | C8B—C13B—H13B | 118.5 |
C15A—C14A—H14A | 109.8 | N2B—C14B—C15B | 112.6 (3) |
N2A—C14A—H14B | 109.8 | N2B—C14B—H14C | 109.1 |
C15A—C14A—H14B | 109.8 | C15B—C14B—H14C | 109.1 |
H14A—C14A—H14B | 108.2 | N2B—C14B—H14D | 109.1 |
N2A—C14C—C15C | 109.4 (3) | C15B—C14B—H14D | 109.1 |
N2A—C14C—H14E | 109.8 | H14C—C14B—H14D | 107.8 |
C15C—C14C—H14E | 109.8 | C14B—C15B—H15D | 109.5 |
N2A—C14C—H14F | 109.8 | C14B—C15B—H15E | 109.5 |
C15C—C14C—H14F | 109.8 | H15D—C15B—H15E | 109.5 |
H14E—C14C—H14F | 108.2 | C14B—C15B—H15F | 109.5 |
C14C—C15C—H15G | 109.5 | H15D—C15B—H15F | 109.5 |
C14C—C15C—H15H | 109.5 | H15E—C15B—H15F | 109.5 |
H15G—C15C—H15H | 109.5 | N2B—C16B—C17B | 112.2 (3) |
C14C—C15C—H15I | 109.5 | N2B—C16B—H16C | 109.2 |
H15G—C15C—H15I | 109.5 | C17B—C16B—H16C | 109.2 |
H15H—C15C—H15I | 109.5 | N2B—C16B—H16D | 109.2 |
N2A—C16A—C17A | 115.1 (3) | C17B—C16B—H16D | 109.2 |
N2A—C16A—H16A | 108.5 | H16C—C16B—H16D | 107.9 |
C17A—C16A—H16A | 108.5 | C16B—C17B—H17D | 109.5 |
N2A—C16A—H16B | 108.5 | C16B—C17B—H17E | 109.5 |
C17A—C16A—H16B | 108.5 | H17D—C17B—H17E | 109.5 |
H16A—C16A—H16B | 107.5 | C16B—C17B—H17F | 109.5 |
C16A—C17A—H17A | 109.5 | H17D—C17B—H17F | 109.5 |
C16A—C17A—H17B | 109.5 | H17E—C17B—H17F | 109.5 |
H17A—C17A—H17B | 109.5 | C5B—C18B—C19B | 132.9 (2) |
C16A—C17A—H17C | 109.5 | C5B—C18B—H18B | 113.5 |
H17A—C17A—H17C | 109.5 | C19B—C18B—H18B | 113.5 |
H17B—C17A—H17C | 109.5 | C24B—C19B—C20B | 116.0 (2) |
C5A—C18A—C19A | 131.6 (3) | C24B—C19B—C18B | 116.7 (2) |
C5A—C18A—H18A | 114.2 | C20B—C19B—C18B | 127.2 (2) |
C19A—C18A—H18A | 114.2 | C21B—C20B—C19B | 122.0 (2) |
C24A—C19A—C20A | 116.0 (2) | C21B—C20B—H20B | 119.0 |
C24A—C19A—C18A | 118.0 (2) | C19B—C20B—H20B | 119.0 |
C20A—C19A—C18A | 126.0 (2) | C20B—C21B—C22B | 121.7 (2) |
C21A—C20A—C19A | 121.9 (3) | C20B—C21B—H21B | 119.2 |
C21A—C20A—H20A | 119.1 | C22B—C21B—H21B | 119.2 |
C19A—C20A—H20A | 119.1 | N3B—C22B—C21B | 122.2 (2) |
C20A—C21A—C22A | 121.7 (2) | N3B—C22B—C23B | 121.0 (2) |
C20A—C21A—H21A | 119.2 | C21B—C22B—C23B | 116.7 (2) |
C22A—C21A—H21A | 119.2 | C24B—C23B—C22B | 120.4 (2) |
N3A—C22A—C21A | 122.5 (2) | C24B—C23B—H23B | 119.8 |
N3A—C22A—C23A | 120.8 (2) | C22B—C23B—H23B | 119.8 |
C21A—C22A—C23A | 116.6 (2) | C23B—C24B—C19B | 123.1 (2) |
C24A—C23A—C22A | 120.8 (2) | C23B—C24B—H24B | 118.4 |
C24A—C23A—H23A | 119.6 | C19B—C24B—H24B | 118.4 |
C22A—C23A—H23A | 119.6 | N3B—C25B—C26B | 114.5 (2) |
C23A—C24A—C19A | 123.0 (2) | N3B—C25B—H25C | 108.6 |
C23A—C24A—H24A | 118.5 | C26B—C25B—H25C | 108.6 |
C19A—C24A—H24A | 118.5 | N3B—C25B—H25D | 108.6 |
N3A—C25A—C26A | 113.3 (2) | C26B—C25B—H25D | 108.6 |
N3A—C25A—H25A | 108.9 | H25C—C25B—H25D | 107.6 |
C26A—C25A—H25A | 108.9 | C25B—C26B—H26D | 109.5 |
N3A—C25A—H25B | 108.9 | C25B—C26B—H26E | 109.5 |
C26A—C25A—H25B | 108.9 | H26D—C26B—H26E | 109.5 |
H25A—C25A—H25B | 107.7 | C25B—C26B—H26F | 109.5 |
C25A—C26A—H26A | 109.5 | H26D—C26B—H26F | 109.5 |
C25A—C26A—H26B | 109.5 | H26E—C26B—H26F | 109.5 |
H26A—C26A—H26B | 109.5 | N3B—C27B—C28B | 112.6 (2) |
C25A—C26A—H26C | 109.5 | N3B—C27B—H27C | 109.1 |
H26A—C26A—H26C | 109.5 | C28B—C27B—H27C | 109.1 |
H26B—C26A—H26C | 109.5 | N3B—C27B—H27D | 109.1 |
N3A—C27A—C28A | 113.7 (2) | C28B—C27B—H27D | 109.1 |
N3A—C27A—H27A | 108.8 | H27C—C27B—H27D | 107.8 |
C28A—C27A—H27A | 108.8 | C27B—C28B—H28D | 109.5 |
N3A—C27A—H27B | 108.8 | C27B—C28B—H28E | 109.5 |
C28A—C27A—H27B | 108.8 | H28D—C28B—H28E | 109.5 |
H27A—C27A—H27B | 107.7 | C27B—C28B—H28F | 109.5 |
C27A—C28A—H28A | 109.5 | H28D—C28B—H28F | 109.5 |
C27A—C28A—H28B | 109.5 | H28E—C28B—H28F | 109.5 |
H28A—C28A—H28B | 109.5 | O3B—C29B—O2B | 123.6 (2) |
C27A—C28A—H28C | 109.5 | O3B—C29B—C30B | 122.3 (2) |
H28A—C28A—H28C | 109.5 | O2B—C29B—C30B | 114.1 (2) |
H28B—C28A—H28C | 109.5 | C30Bii—C30B—C29B | 113.2 (3) |
O3A—C29A—O2A | 123.1 (2) | C30Bii—C30B—H30C | 108.9 |
O3A—C29A—C30A | 121.6 (2) | C29B—C30B—H30C | 108.9 |
O2A—C29A—C30A | 115.3 (2) | C30Bii—C30B—H30D | 108.9 |
C29A—C30A—C30Ai | 114.4 (3) | C29B—C30B—H30D | 108.9 |
C29A—C30A—H30A | 108.7 | H30C—C30B—H30D | 107.7 |
C6A—N1A—C2A—C3A | −54.7 (3) | C25A—N3A—C27A—C28A | 94.0 (3) |
N1A—C2A—C3A—C7A | −148.4 (3) | O3A—C29A—C30A—C30Ai | 10.3 (5) |
N1A—C2A—C3A—C4A | 29.1 (3) | O2A—C29A—C30A—C30Ai | −172.2 (3) |
C7A—C3A—C4A—O1A | −8.5 (4) | C6B—N1B—C2B—C3B | −59.1 (3) |
C2A—C3A—C4A—O1A | 173.8 (2) | N1B—C2B—C3B—C7B | −152.7 (2) |
C7A—C3A—C4A—C5A | 170.4 (2) | N1B—C2B—C3B—C4B | 22.9 (3) |
C2A—C3A—C4A—C5A | −7.3 (4) | C7B—C3B—C4B—O1B | 6.0 (4) |
O1A—C4A—C5A—C18A | 12.0 (4) | C2B—C3B—C4B—O1B | −169.9 (3) |
C3A—C4A—C5A—C18A | −166.8 (2) | C7B—C3B—C4B—C5B | −173.6 (2) |
O1A—C4A—C5A—C6A | −171.2 (3) | C2B—C3B—C4B—C5B | 10.5 (4) |
C3A—C4A—C5A—C6A | 9.9 (4) | O1B—C4B—C5B—C18B | −9.9 (4) |
C2A—N1A—C6A—C5A | 57.4 (3) | C3B—C4B—C5B—C18B | 169.7 (2) |
C18A—C5A—C6A—N1A | 142.1 (3) | O1B—C4B—C5B—C6B | 171.2 (3) |
C4A—C5A—C6A—N1A | −34.3 (3) | C3B—C4B—C5B—C6B | −9.2 (4) |
C4A—C3A—C7A—C8A | 178.5 (3) | C2B—N1B—C6B—C5B | 60.1 (3) |
C2A—C3A—C7A—C8A | −3.9 (5) | C18B—C5B—C6B—N1B | 156.1 (3) |
C3A—C7A—C8A—C13A | 156.3 (3) | C4B—C5B—C6B—N1B | −25.1 (3) |
C3A—C7A—C8A—C9A | −27.0 (5) | C4B—C3B—C7B—C8B | −173.8 (3) |
C13A—C8A—C9A—C10A | −2.2 (5) | C2B—C3B—C7B—C8B | 1.8 (5) |
C7A—C8A—C9A—C10A | −179.0 (3) | C3B—C7B—C8B—C13B | 156.7 (3) |
C8A—C9A—C10A—C11A | 0.2 (6) | C3B—C7B—C8B—C9B | −21.3 (5) |
C16A—N2A—C11A—C12A | 5.1 (6) | C13B—C8B—C9B—C10B | −3.2 (4) |
C14C—N2A—C11A—C12A | 145.5 (4) | C7B—C8B—C9B—C10B | 174.9 (3) |
C14A—N2A—C11A—C12A | −166.9 (3) | C8B—C9B—C10B—C11B | −1.8 (4) |
C16A—N2A—C11A—C10A | −176.3 (4) | C16B—N2B—C11B—C12B | 2.5 (4) |
C14C—N2A—C11A—C10A | −35.9 (6) | C14B—N2B—C11B—C12B | 169.5 (3) |
C14A—N2A—C11A—C10A | 11.7 (6) | C16B—N2B—C11B—C10B | −178.0 (3) |
C9A—C10A—C11A—N2A | −177.3 (4) | C14B—N2B—C11B—C10B | −11.1 (4) |
C9A—C10A—C11A—C12A | 1.4 (5) | C9B—C10B—C11B—N2B | −174.3 (3) |
N2A—C11A—C12A—C13A | 177.9 (3) | C9B—C10B—C11B—C12B | 5.2 (4) |
C10A—C11A—C12A—C13A | −0.8 (5) | N2B—C11B—C12B—C13B | 175.9 (3) |
C11A—C12A—C13A—C8A | −1.3 (4) | C10B—C11B—C12B—C13B | −3.6 (4) |
C9A—C8A—C13A—C12A | 2.8 (4) | C11B—C12B—C13B—C8B | −1.3 (4) |
C7A—C8A—C13A—C12A | 179.9 (3) | C9B—C8B—C13B—C12B | 4.7 (4) |
C11A—N2A—C14A—C15A | −93.6 (5) | C7B—C8B—C13B—C12B | −173.5 (3) |
C16A—N2A—C14A—C15A | 94.1 (5) | C11B—N2B—C14B—C15B | 88.1 (3) |
C14C—N2A—C14A—C15A | −0.7 (5) | C16B—N2B—C14B—C15B | −104.1 (3) |
C11A—N2A—C14C—C15C | 104.9 (6) | C11B—N2B—C16B—C17B | 82.7 (4) |
C16A—N2A—C14C—C15C | −111.1 (6) | C14B—N2B—C16B—C17B | −85.0 (3) |
C14A—N2A—C14C—C15C | −6.1 (5) | C4B—C5B—C18B—C19B | −173.2 (3) |
C11A—N2A—C16A—C17A | 78.5 (4) | C6B—C5B—C18B—C19B | 5.6 (5) |
C14C—N2A—C16A—C17A | −62.9 (4) | C5B—C18B—C19B—C24B | 177.8 (3) |
C14A—N2A—C16A—C17A | −109.1 (4) | C5B—C18B—C19B—C20B | 2.0 (5) |
C4A—C5A—C18A—C19A | −179.8 (3) | C24B—C19B—C20B—C21B | 0.3 (4) |
C6A—C5A—C18A—C19A | 3.7 (5) | C18B—C19B—C20B—C21B | 176.1 (3) |
C5A—C18A—C19A—C24A | −159.5 (3) | C19B—C20B—C21B—C22B | −2.9 (4) |
C5A—C18A—C19A—C20A | 24.1 (5) | C25B—N3B—C22B—C21B | −3.6 (4) |
C24A—C19A—C20A—C21A | 0.5 (4) | C27B—N3B—C22B—C21B | 177.9 (3) |
C18A—C19A—C20A—C21A | 177.0 (3) | C25B—N3B—C22B—C23B | 179.5 (3) |
C19A—C20A—C21A—C22A | 0.4 (4) | C27B—N3B—C22B—C23B | 0.9 (4) |
C27A—N3A—C22A—C21A | −169.4 (2) | C20B—C21B—C22B—N3B | −173.5 (3) |
C25A—N3A—C22A—C21A | 4.4 (4) | C20B—C21B—C22B—C23B | 3.6 (4) |
C27A—N3A—C22A—C23A | 13.7 (4) | N3B—C22B—C23B—C24B | 175.3 (3) |
C25A—N3A—C22A—C23A | −172.5 (2) | C21B—C22B—C23B—C24B | −1.8 (4) |
C20A—C21A—C22A—N3A | −177.4 (3) | C22B—C23B—C24B—C19B | −0.8 (4) |
C20A—C21A—C22A—C23A | −0.4 (4) | C20B—C19B—C24B—C23B | 1.5 (4) |
N3A—C22A—C23A—C24A | 176.6 (2) | C18B—C19B—C24B—C23B | −174.7 (3) |
C21A—C22A—C23A—C24A | −0.5 (4) | C22B—N3B—C25B—C26B | −80.6 (3) |
C22A—C23A—C24A—C19A | 1.4 (4) | C27B—N3B—C25B—C26B | 97.9 (3) |
C20A—C19A—C24A—C23A | −1.4 (4) | C22B—N3B—C27B—C28B | 81.2 (3) |
C18A—C19A—C24A—C23A | −178.2 (2) | C25B—N3B—C27B—C28B | −97.4 (3) |
C22A—N3A—C25A—C26A | −85.9 (3) | O3B—C29B—C30B—C30Bii | 4.1 (4) |
C27A—N3A—C25A—C26A | 88.3 (3) | O2B—C29B—C30B—C30Bii | −177.3 (3) |
C22A—N3A—C27A—C28A | −91.8 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1B···O2A | 0.93 | 1.61 | 2.538 (3) | 173 |
N1B—H1C···O3Ai | 0.90 | 1.97 | 2.833 (3) | 161 |
N1B—H1D···O2B | 0.94 | 1.63 | 2.561 (3) | 174 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
2C27H36N3O+·C10H16O42− | Z = 1 |
Mr = 1037.40 | F(000) = 562 |
Triclinic, P1 | Dx = 1.209 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2905 (8) Å | Cell parameters from 1012 reflections |
b = 12.7532 (13) Å | θ = 2.4–20.3° |
c = 14.0762 (14) Å | µ = 0.08 mm−1 |
α = 87.076 (2)° | T = 100 K |
β = 77.516 (2)° | Plate, red |
γ = 78.660 (2)° | 0.15 × 0.10 × 0.02 mm |
V = 1424.7 (2) Å3 |
Bruker APEXII CCD area-detector diffractometer | 7586 independent reflections |
Radiation source: fine-focus sealed tube | 5558 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
φ and ω scans | θmax = 29.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −11→11 |
Tmin = 0.989, Tmax = 0.998 | k = −17→17 |
17369 measured reflections | l = −19→19 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0554P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3 |
7586 reflections | (Δ/σ)max = 0.001 |
355 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.59902 (14) | 0.60180 (8) | 0.89599 (7) | 0.0276 (2) | |
N1 | 0.69851 (13) | 0.51716 (8) | 0.61076 (7) | 0.0165 (2) | |
H1A | 0.5880 | 0.5201 | 0.6187 | 0.020* | |
H1B | 0.7508 | 0.4990 | 0.5463 | 0.020* | |
N2 | 0.56579 (15) | 1.17048 (9) | 0.57569 (9) | 0.0254 (3) | |
N3 | 0.85021 (14) | −0.06577 (9) | 0.87313 (8) | 0.0220 (2) | |
C2 | 0.72551 (16) | 0.62570 (10) | 0.62708 (9) | 0.0174 (2) | |
H2A | 0.6663 | 0.6776 | 0.5854 | 0.021* | |
H2B | 0.8472 | 0.6271 | 0.6075 | 0.021* | |
C3 | 0.66330 (15) | 0.65947 (10) | 0.73163 (9) | 0.0171 (2) | |
C4 | 0.65092 (16) | 0.57603 (10) | 0.81004 (9) | 0.0186 (3) | |
C5 | 0.70388 (15) | 0.46187 (10) | 0.78150 (9) | 0.0170 (2) | |
C6 | 0.77337 (16) | 0.43551 (10) | 0.67543 (8) | 0.0167 (2) | |
H6A | 0.8969 | 0.4305 | 0.6610 | 0.020* | |
H6B | 0.7503 | 0.3650 | 0.6622 | 0.020* | |
C7 | 0.61652 (15) | 0.76243 (10) | 0.76075 (9) | 0.0180 (3) | |
H7 | 0.5779 | 0.7702 | 0.8291 | 0.022* | |
C8 | 0.61377 (16) | 0.86319 (10) | 0.70808 (9) | 0.0182 (3) | |
C9 | 0.68919 (16) | 0.87855 (11) | 0.60996 (9) | 0.0201 (3) | |
H9 | 0.7513 | 0.8183 | 0.5725 | 0.024* | |
C10 | 0.67564 (17) | 0.97840 (11) | 0.56669 (10) | 0.0220 (3) | |
H10 | 0.7284 | 0.9851 | 0.5003 | 0.026* | |
C11 | 0.58503 (16) | 1.07112 (10) | 0.61879 (10) | 0.0207 (3) | |
C12 | 0.51516 (17) | 1.05680 (11) | 0.71839 (10) | 0.0215 (3) | |
H12 | 0.4570 | 1.1172 | 0.7569 | 0.026* | |
C13 | 0.53041 (16) | 0.95651 (11) | 0.76011 (9) | 0.0201 (3) | |
H13 | 0.4823 | 0.9499 | 0.8273 | 0.024* | |
C14 | 0.66240 (17) | 1.18755 (11) | 0.47834 (10) | 0.0243 (3) | |
H14A | 0.6092 | 1.2558 | 0.4517 | 0.029* | |
H14B | 0.6584 | 1.1293 | 0.4355 | 0.029* | |
C15 | 0.84530 (18) | 1.19104 (12) | 0.47672 (10) | 0.0266 (3) | |
H15A | 0.9043 | 1.2011 | 0.4096 | 0.040* | |
H15B | 0.8990 | 1.1237 | 0.5029 | 0.040* | |
H15C | 0.8505 | 1.2506 | 0.5166 | 0.040* | |
C16 | 0.46798 (18) | 1.26407 (11) | 0.63129 (11) | 0.0257 (3) | |
H16A | 0.4932 | 1.3296 | 0.5951 | 0.031* | |
H16B | 0.5030 | 1.2639 | 0.6942 | 0.031* | |
C17 | 0.27894 (18) | 1.26727 (12) | 0.65061 (11) | 0.0293 (3) | |
H17A | 0.2205 | 1.3257 | 0.6953 | 0.044* | |
H17B | 0.2545 | 1.1992 | 0.6798 | 0.044* | |
H17C | 0.2404 | 1.2790 | 0.5892 | 0.044* | |
C18 | 0.68463 (16) | 0.38801 (10) | 0.85356 (9) | 0.0181 (3) | |
H18 | 0.6309 | 0.4173 | 0.9157 | 0.022* | |
C19 | 0.73132 (16) | 0.27228 (10) | 0.85293 (9) | 0.0179 (2) | |
C20 | 0.84865 (16) | 0.21016 (11) | 0.77978 (9) | 0.0196 (3) | |
H20 | 0.9018 | 0.2452 | 0.7240 | 0.024* | |
C21 | 0.88917 (16) | 0.10029 (11) | 0.78628 (9) | 0.0202 (3) | |
H21 | 0.9691 | 0.0617 | 0.7351 | 0.024* | |
C22 | 0.81410 (16) | 0.04376 (10) | 0.86766 (9) | 0.0191 (3) | |
C23 | 0.70082 (17) | 0.10605 (11) | 0.94272 (9) | 0.0217 (3) | |
H23 | 0.6508 | 0.0715 | 0.9997 | 0.026* | |
C24 | 0.66114 (17) | 0.21572 (11) | 0.93520 (9) | 0.0211 (3) | |
H24 | 0.5838 | 0.2546 | 0.9872 | 0.025* | |
C25 | 0.96848 (17) | −0.12879 (11) | 0.79549 (10) | 0.0232 (3) | |
H25A | 0.9503 | −0.0967 | 0.7322 | 0.028* | |
H25B | 0.9437 | −0.2019 | 0.7986 | 0.028* | |
C26 | 1.15265 (18) | −0.13694 (12) | 0.79899 (11) | 0.0278 (3) | |
H26A | 1.2236 | −0.1820 | 0.7456 | 0.042* | |
H26B | 1.1725 | −0.1687 | 0.8613 | 0.042* | |
H26C | 1.1806 | −0.0654 | 0.7922 | 0.042* | |
C27 | 0.77194 (18) | −0.12394 (12) | 0.95737 (10) | 0.0253 (3) | |
H27A | 0.7720 | −0.1971 | 0.9371 | 0.030* | |
H27B | 0.6532 | −0.0879 | 0.9792 | 0.030* | |
C28 | 0.8590 (2) | −0.13158 (13) | 1.04257 (11) | 0.0317 (3) | |
H28A | 0.7974 | −0.1685 | 1.0971 | 0.048* | |
H28B | 0.8616 | −0.0595 | 1.0625 | 0.048* | |
H28C | 0.9744 | −0.1717 | 1.0231 | 0.048* | |
O2 | 0.63112 (12) | 0.44419 (8) | 0.40128 (7) | 0.0248 (2) | |
O3 | 0.86938 (11) | 0.47165 (8) | 0.43417 (6) | 0.0222 (2) | |
C29 | 0.78091 (16) | 0.45307 (10) | 0.37599 (9) | 0.0167 (2) | |
C30 | 0.87086 (16) | 0.43889 (11) | 0.26976 (9) | 0.0202 (3) | |
H30A | 0.9376 | 0.4960 | 0.2516 | 0.024* | |
H30B | 0.9508 | 0.3696 | 0.2633 | 0.024* | |
C31 | 0.75748 (18) | 0.44158 (13) | 0.19799 (10) | 0.0271 (3) | |
H31A | 0.6806 | 0.5120 | 0.2017 | 0.033* | |
H31B | 0.6878 | 0.3861 | 0.2167 | 0.033* | |
C32 | 0.8557 (2) | 0.42265 (14) | 0.09303 (10) | 0.0330 (4) | |
H32A | 0.9379 | 0.3545 | 0.0905 | 0.040* | |
H32B | 0.7764 | 0.4150 | 0.0515 | 0.040* | |
C33 | 0.9489 (2) | 0.51130 (13) | 0.05157 (10) | 0.0315 (3) | |
H33A | 1.0254 | 0.5209 | 0.0942 | 0.038* | |
H33B | 0.8666 | 0.5790 | 0.0514 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0430 (6) | 0.0222 (5) | 0.0141 (4) | −0.0019 (4) | −0.0022 (4) | −0.0021 (4) |
N1 | 0.0179 (5) | 0.0208 (5) | 0.0115 (5) | −0.0050 (4) | −0.0033 (4) | −0.0008 (4) |
N2 | 0.0244 (6) | 0.0212 (6) | 0.0258 (6) | −0.0029 (5) | 0.0027 (5) | 0.0041 (5) |
N3 | 0.0253 (6) | 0.0196 (6) | 0.0197 (5) | −0.0042 (5) | −0.0015 (4) | −0.0009 (4) |
C2 | 0.0199 (6) | 0.0186 (6) | 0.0142 (6) | −0.0054 (5) | −0.0032 (5) | 0.0002 (4) |
C3 | 0.0168 (6) | 0.0214 (6) | 0.0142 (5) | −0.0054 (5) | −0.0040 (4) | 0.0008 (5) |
C4 | 0.0211 (6) | 0.0209 (6) | 0.0143 (6) | −0.0043 (5) | −0.0045 (5) | 0.0004 (5) |
C5 | 0.0170 (6) | 0.0209 (6) | 0.0137 (5) | −0.0038 (5) | −0.0038 (4) | −0.0013 (5) |
C6 | 0.0189 (6) | 0.0177 (6) | 0.0137 (5) | −0.0038 (5) | −0.0033 (4) | −0.0001 (4) |
C7 | 0.0176 (6) | 0.0224 (6) | 0.0150 (6) | −0.0050 (5) | −0.0041 (5) | −0.0003 (5) |
C8 | 0.0181 (6) | 0.0201 (6) | 0.0175 (6) | −0.0056 (5) | −0.0045 (5) | −0.0007 (5) |
C9 | 0.0202 (6) | 0.0204 (6) | 0.0192 (6) | −0.0046 (5) | −0.0017 (5) | −0.0028 (5) |
C10 | 0.0239 (7) | 0.0234 (7) | 0.0184 (6) | −0.0070 (5) | −0.0014 (5) | 0.0012 (5) |
C11 | 0.0191 (6) | 0.0197 (6) | 0.0234 (6) | −0.0052 (5) | −0.0037 (5) | 0.0019 (5) |
C12 | 0.0227 (7) | 0.0192 (6) | 0.0217 (6) | −0.0036 (5) | −0.0030 (5) | −0.0021 (5) |
C13 | 0.0207 (6) | 0.0239 (7) | 0.0165 (6) | −0.0067 (5) | −0.0033 (5) | −0.0002 (5) |
C14 | 0.0262 (7) | 0.0241 (7) | 0.0217 (6) | −0.0066 (6) | −0.0029 (5) | 0.0055 (5) |
C15 | 0.0266 (7) | 0.0277 (7) | 0.0246 (7) | −0.0089 (6) | 0.0000 (6) | −0.0012 (6) |
C16 | 0.0283 (7) | 0.0175 (6) | 0.0302 (7) | −0.0051 (6) | −0.0035 (6) | 0.0011 (5) |
C17 | 0.0274 (7) | 0.0255 (7) | 0.0314 (8) | −0.0009 (6) | −0.0030 (6) | 0.0023 (6) |
C18 | 0.0190 (6) | 0.0211 (6) | 0.0137 (5) | −0.0028 (5) | −0.0030 (5) | −0.0017 (5) |
C19 | 0.0191 (6) | 0.0208 (6) | 0.0142 (6) | −0.0045 (5) | −0.0040 (5) | 0.0002 (5) |
C20 | 0.0201 (6) | 0.0237 (7) | 0.0146 (6) | −0.0047 (5) | −0.0027 (5) | 0.0026 (5) |
C21 | 0.0213 (6) | 0.0233 (7) | 0.0146 (6) | −0.0026 (5) | −0.0015 (5) | −0.0020 (5) |
C22 | 0.0190 (6) | 0.0206 (6) | 0.0185 (6) | −0.0038 (5) | −0.0052 (5) | −0.0009 (5) |
C23 | 0.0230 (7) | 0.0233 (7) | 0.0172 (6) | −0.0051 (5) | −0.0013 (5) | 0.0028 (5) |
C24 | 0.0214 (6) | 0.0241 (7) | 0.0151 (6) | −0.0015 (5) | −0.0006 (5) | −0.0011 (5) |
C25 | 0.0250 (7) | 0.0210 (7) | 0.0233 (7) | −0.0043 (5) | −0.0032 (5) | −0.0056 (5) |
C26 | 0.0254 (7) | 0.0317 (8) | 0.0255 (7) | −0.0044 (6) | −0.0038 (6) | −0.0034 (6) |
C27 | 0.0260 (7) | 0.0230 (7) | 0.0279 (7) | −0.0077 (6) | −0.0053 (6) | 0.0012 (5) |
C28 | 0.0332 (8) | 0.0343 (8) | 0.0269 (7) | −0.0035 (7) | −0.0073 (6) | −0.0004 (6) |
O2 | 0.0187 (5) | 0.0358 (6) | 0.0197 (5) | −0.0066 (4) | −0.0026 (4) | 0.0009 (4) |
O3 | 0.0218 (5) | 0.0319 (5) | 0.0142 (4) | −0.0082 (4) | −0.0033 (3) | −0.0022 (4) |
C29 | 0.0191 (6) | 0.0156 (6) | 0.0149 (6) | −0.0026 (5) | −0.0035 (5) | 0.0007 (4) |
C30 | 0.0206 (6) | 0.0260 (7) | 0.0146 (6) | −0.0057 (5) | −0.0035 (5) | −0.0026 (5) |
C31 | 0.0254 (7) | 0.0434 (9) | 0.0163 (6) | −0.0139 (6) | −0.0059 (5) | 0.0002 (6) |
C32 | 0.0401 (9) | 0.0482 (10) | 0.0166 (6) | −0.0218 (8) | −0.0067 (6) | −0.0007 (6) |
C33 | 0.0404 (9) | 0.0392 (9) | 0.0174 (7) | −0.0148 (7) | −0.0052 (6) | 0.0018 (6) |
O1—C4 | 1.2317 (15) | C17—H17A | 0.9800 |
N1—C6 | 1.4803 (15) | C17—H17B | 0.9800 |
N1—C2 | 1.4818 (16) | C17—H17C | 0.9800 |
N1—H1A | 0.8925 | C18—C19 | 1.4503 (18) |
N1—H1B | 0.9360 | C18—H18 | 0.9500 |
N2—C11 | 1.3722 (17) | C19—C20 | 1.4076 (18) |
N2—C14 | 1.4596 (17) | C19—C24 | 1.4101 (17) |
N2—C16 | 1.4611 (18) | C20—C21 | 1.3782 (19) |
N3—C22 | 1.3717 (17) | C20—H20 | 0.9500 |
N3—C25 | 1.4554 (17) | C21—C22 | 1.4155 (18) |
N3—C27 | 1.4643 (17) | C21—H21 | 0.9500 |
C2—C3 | 1.5055 (17) | C22—C23 | 1.4116 (18) |
C2—H2A | 0.9900 | C23—C24 | 1.3764 (19) |
C2—H2B | 0.9900 | C23—H23 | 0.9500 |
C3—C7 | 1.3522 (18) | C24—H24 | 0.9500 |
C3—C4 | 1.4951 (17) | C25—C26 | 1.521 (2) |
C4—C5 | 1.4852 (18) | C25—H25A | 0.9900 |
C5—C18 | 1.3540 (17) | C25—H25B | 0.9900 |
C5—C6 | 1.5090 (16) | C26—H26A | 0.9800 |
C6—H6A | 0.9900 | C26—H26B | 0.9800 |
C6—H6B | 0.9900 | C26—H26C | 0.9800 |
C7—C8 | 1.4492 (18) | C27—C28 | 1.518 (2) |
C7—H7 | 0.9500 | C27—H27A | 0.9900 |
C8—C13 | 1.4061 (18) | C27—H27B | 0.9900 |
C8—C9 | 1.4086 (17) | C28—H28A | 0.9800 |
C9—C10 | 1.3781 (19) | C28—H28B | 0.9800 |
C9—H9 | 0.9500 | C28—H28C | 0.9800 |
C10—C11 | 1.4148 (19) | O2—C29 | 1.2417 (15) |
C10—H10 | 0.9500 | O3—C29 | 1.2699 (15) |
C11—C12 | 1.4138 (18) | C29—C30 | 1.5222 (17) |
C12—C13 | 1.3742 (18) | C30—C31 | 1.5165 (18) |
C12—H12 | 0.9500 | C30—H30A | 0.9900 |
C13—H13 | 0.9500 | C30—H30B | 0.9900 |
C14—C15 | 1.5209 (19) | C31—C32 | 1.5308 (19) |
C14—H14A | 0.9900 | C31—H31A | 0.9900 |
C14—H14B | 0.9900 | C31—H31B | 0.9900 |
C15—H15A | 0.9800 | C32—C33 | 1.516 (2) |
C15—H15B | 0.9800 | C32—H32A | 0.9900 |
C15—H15C | 0.9800 | C32—H32B | 0.9900 |
C16—C17 | 1.524 (2) | C33—C33i | 1.524 (3) |
C16—H16A | 0.9900 | C33—H33A | 0.9900 |
C16—H16B | 0.9900 | C33—H33B | 0.9900 |
C6—N1—C2 | 112.61 (9) | C16—C17—H17C | 109.5 |
C6—N1—H1A | 111.5 | H17A—C17—H17C | 109.5 |
C2—N1—H1A | 107.9 | H17B—C17—H17C | 109.5 |
C6—N1—H1B | 108.1 | C5—C18—C19 | 131.59 (12) |
C2—N1—H1B | 107.4 | C5—C18—H18 | 114.2 |
H1A—N1—H1B | 109.2 | C19—C18—H18 | 114.2 |
C11—N2—C14 | 120.58 (12) | C20—C19—C24 | 116.00 (12) |
C11—N2—C16 | 120.59 (11) | C20—C19—C18 | 126.08 (11) |
C14—N2—C16 | 118.20 (11) | C24—C19—C18 | 117.82 (11) |
C22—N3—C25 | 121.25 (11) | C21—C20—C19 | 122.30 (12) |
C22—N3—C27 | 121.39 (11) | C21—C20—H20 | 118.9 |
C25—N3—C27 | 117.35 (11) | C19—C20—H20 | 118.9 |
N1—C2—C3 | 112.45 (10) | C20—C21—C22 | 121.36 (12) |
N1—C2—H2A | 109.1 | C20—C21—H21 | 119.3 |
C3—C2—H2A | 109.1 | C22—C21—H21 | 119.3 |
N1—C2—H2B | 109.1 | N3—C22—C23 | 121.94 (12) |
C3—C2—H2B | 109.1 | N3—C22—C21 | 121.58 (12) |
H2A—C2—H2B | 107.8 | C23—C22—C21 | 116.48 (12) |
C7—C3—C4 | 116.45 (11) | C24—C23—C22 | 121.52 (12) |
C7—C3—C2 | 124.10 (11) | C24—C23—H23 | 119.2 |
C4—C3—C2 | 119.45 (11) | C22—C23—H23 | 119.2 |
O1—C4—C5 | 121.16 (11) | C23—C24—C19 | 122.26 (12) |
O1—C4—C3 | 120.57 (12) | C23—C24—H24 | 118.9 |
C5—C4—C3 | 118.28 (11) | C19—C24—H24 | 118.9 |
C18—C5—C4 | 116.98 (11) | N3—C25—C26 | 114.53 (11) |
C18—C5—C6 | 124.38 (11) | N3—C25—H25A | 108.6 |
C4—C5—C6 | 118.64 (10) | C26—C25—H25A | 108.6 |
N1—C6—C5 | 111.91 (10) | N3—C25—H25B | 108.6 |
N1—C6—H6A | 109.2 | C26—C25—H25B | 108.6 |
C5—C6—H6A | 109.2 | H25A—C25—H25B | 107.6 |
N1—C6—H6B | 109.2 | C25—C26—H26A | 109.5 |
C5—C6—H6B | 109.2 | C25—C26—H26B | 109.5 |
H6A—C6—H6B | 107.9 | H26A—C26—H26B | 109.5 |
C3—C7—C8 | 132.57 (12) | C25—C26—H26C | 109.5 |
C3—C7—H7 | 113.7 | H26A—C26—H26C | 109.5 |
C8—C7—H7 | 113.7 | H26B—C26—H26C | 109.5 |
C13—C8—C9 | 115.80 (12) | N3—C27—C28 | 113.85 (12) |
C13—C8—C7 | 117.23 (11) | N3—C27—H27A | 108.8 |
C9—C8—C7 | 126.96 (12) | C28—C27—H27A | 108.8 |
C10—C9—C8 | 121.98 (12) | N3—C27—H27B | 108.8 |
C10—C9—H9 | 119.0 | C28—C27—H27B | 108.8 |
C8—C9—H9 | 119.0 | H27A—C27—H27B | 107.7 |
C9—C10—C11 | 121.59 (12) | C27—C28—H28A | 109.5 |
C9—C10—H10 | 119.2 | C27—C28—H28B | 109.5 |
C11—C10—H10 | 119.2 | H28A—C28—H28B | 109.5 |
N2—C11—C12 | 121.18 (12) | C27—C28—H28C | 109.5 |
N2—C11—C10 | 122.15 (12) | H28A—C28—H28C | 109.5 |
C12—C11—C10 | 116.67 (12) | H28B—C28—H28C | 109.5 |
C13—C12—C11 | 120.73 (12) | O2—C29—O3 | 124.11 (11) |
C13—C12—H12 | 119.6 | O2—C29—C30 | 120.03 (11) |
C11—C12—H12 | 119.6 | O3—C29—C30 | 115.84 (11) |
C12—C13—C8 | 123.12 (12) | C31—C30—C29 | 115.39 (11) |
C12—C13—H13 | 118.4 | C31—C30—H30A | 108.4 |
C8—C13—H13 | 118.4 | C29—C30—H30A | 108.4 |
N2—C14—C15 | 113.10 (12) | C31—C30—H30B | 108.4 |
N2—C14—H14A | 109.0 | C29—C30—H30B | 108.4 |
C15—C14—H14A | 109.0 | H30A—C30—H30B | 107.5 |
N2—C14—H14B | 109.0 | C30—C31—C32 | 112.84 (12) |
C15—C14—H14B | 109.0 | C30—C31—H31A | 109.0 |
H14A—C14—H14B | 107.8 | C32—C31—H31A | 109.0 |
C14—C15—H15A | 109.5 | C30—C31—H31B | 109.0 |
C14—C15—H15B | 109.5 | C32—C31—H31B | 109.0 |
H15A—C15—H15B | 109.5 | H31A—C31—H31B | 107.8 |
C14—C15—H15C | 109.5 | C33—C32—C31 | 113.78 (13) |
H15A—C15—H15C | 109.5 | C33—C32—H32A | 108.8 |
H15B—C15—H15C | 109.5 | C31—C32—H32A | 108.8 |
N2—C16—C17 | 112.81 (12) | C33—C32—H32B | 108.8 |
N2—C16—H16A | 109.0 | C31—C32—H32B | 108.8 |
C17—C16—H16A | 109.0 | H32A—C32—H32B | 107.7 |
N2—C16—H16B | 109.0 | C32—C33—C33i | 112.81 (16) |
C17—C16—H16B | 109.0 | C32—C33—H33A | 109.0 |
H16A—C16—H16B | 107.8 | C33i—C33—H33A | 109.0 |
C16—C17—H17A | 109.5 | C32—C33—H33B | 109.0 |
C16—C17—H17B | 109.5 | C33i—C33—H33B | 109.0 |
H17A—C17—H17B | 109.5 | H33A—C33—H33B | 107.8 |
C6—N1—C2—C3 | −54.87 (14) | C11—N2—C14—C15 | −75.53 (17) |
N1—C2—C3—C7 | −155.30 (12) | C16—N2—C14—C15 | 95.50 (15) |
N1—C2—C3—C4 | 24.71 (16) | C11—N2—C16—C17 | −74.08 (17) |
C7—C3—C4—O1 | 0.63 (19) | C14—N2—C16—C17 | 114.89 (14) |
C2—C3—C4—O1 | −179.38 (12) | C4—C5—C18—C19 | −175.77 (13) |
C7—C3—C4—C5 | −178.94 (11) | C6—C5—C18—C19 | 4.8 (2) |
C2—C3—C4—C5 | 1.05 (17) | C5—C18—C19—C20 | 17.9 (2) |
O1—C4—C5—C18 | 3.15 (19) | C5—C18—C19—C24 | −165.99 (14) |
C3—C4—C5—C18 | −177.28 (11) | C24—C19—C20—C21 | 1.97 (19) |
O1—C4—C5—C6 | −177.40 (12) | C18—C19—C20—C21 | 178.15 (13) |
C3—C4—C5—C6 | 2.17 (17) | C19—C20—C21—C22 | 0.0 (2) |
C2—N1—C6—C5 | 58.13 (13) | C25—N3—C22—C23 | −179.44 (12) |
C18—C5—C6—N1 | 148.43 (12) | C27—N3—C22—C23 | 0.3 (2) |
C4—C5—C6—N1 | −30.98 (15) | C25—N3—C22—C21 | 0.39 (19) |
C4—C3—C7—C8 | 178.66 (13) | C27—N3—C22—C21 | −179.85 (12) |
C2—C3—C7—C8 | −1.3 (2) | C20—C21—C22—N3 | 178.01 (12) |
C3—C7—C8—C13 | 169.59 (13) | C20—C21—C22—C23 | −2.15 (19) |
C3—C7—C8—C9 | −11.9 (2) | N3—C22—C23—C24 | −177.85 (13) |
C13—C8—C9—C10 | −2.74 (19) | C21—C22—C23—C24 | 2.32 (19) |
C7—C8—C9—C10 | 178.72 (13) | C22—C23—C24—C19 | −0.3 (2) |
C8—C9—C10—C11 | 0.1 (2) | C20—C19—C24—C23 | −1.80 (19) |
C14—N2—C11—C12 | 169.05 (12) | C18—C19—C24—C23 | −178.31 (12) |
C16—N2—C11—C12 | −1.8 (2) | C22—N3—C25—C26 | 81.35 (16) |
C14—N2—C11—C10 | −10.6 (2) | C27—N3—C25—C26 | −98.42 (14) |
C16—N2—C11—C10 | 178.56 (13) | C22—N3—C27—C28 | −83.14 (16) |
C9—C10—C11—N2 | −177.74 (13) | C25—N3—C27—C28 | 96.63 (15) |
C9—C10—C11—C12 | 2.6 (2) | O2—C29—C30—C31 | 14.50 (18) |
N2—C11—C12—C13 | 177.85 (13) | O3—C29—C30—C31 | −166.89 (12) |
C10—C11—C12—C13 | −2.45 (19) | C29—C30—C31—C32 | −177.81 (12) |
C11—C12—C13—C8 | −0.3 (2) | C30—C31—C32—C33 | −66.58 (18) |
C9—C8—C13—C12 | 2.87 (19) | C31—C32—C33—C33i | 177.82 (17) |
C7—C8—C13—C12 | −178.44 (12) |
Symmetry code: (i) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2ii | 0.89 | 1.86 | 2.7207 (14) | 161 |
N1—H1B···O3 | 0.94 | 1.68 | 2.6122 (13) | 172 |
Symmetry code: (ii) −x+1, −y+1, −z+1. |