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The importance of using structural mimics for mapping out the structural landscape of a poorly soluble active pharmaceutical ingredient was investigated using erlotinib as an example. A mimic was synthesized by preserving the main molecular functionalities responsible for creating the most probable structural arrangements in the solid state. Calculated molecular electrostatic potentials on both erlotinib and the mimic showed very comparable values indicating that the latter would be able to form hydrogen bonds of similar probability and strength as those of erlotinib. In order to establish the binding preference in co-crystallization experiments, the mimic molecule was co-crystallized with US Food and Drug Administration approved dicarboxylic acids. The crystal structures of the mimic and of four co-crystals thereof were obtained. The mimic forms hydrogen bonds in a way that closely resembles those found in the crystal structure of erlotinib. The four co-crystals display self-consistent hydrogen-bond interactions. Thermal and solubility data for the co-crystals demonstrate that by making systematic and controllable changes to the solid forms of the mimic, it is also possible to alter the behaviour and properties of the new solid forms. The use of a suitable structural mimic can allow for a systematic structural examination of a compound that is otherwise not amenable to such investigations by facilitating the elucidation and mapping out of a closely related structural landscape.
Supporting information
CCDC references: 1588890; 1588891; 1588892; 1588893; 1588894
For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008). Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for MP1601, MP1609, MP1611, MP1614; SHELXL2013 (Sheldrick, 2013) for MP1604. For all structures, molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.
Crystal data top
C18H16N3O2·Cl | Dx = 1.381 Mg m−3 |
Mr = 341.79 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 9849 reflections |
a = 9.507 (2) Å | θ = 2.3–26.1° |
b = 7.9958 (17) Å | µ = 0.25 mm−1 |
c = 43.262 (9) Å | T = 130 K |
V = 3288.6 (12) Å3 | Block, colourless |
Z = 8 | 0.49 × 0.30 × 0.15 mm |
F(000) = 1424 | |
Data collection top
Bruker APEX-II CCD diffractometer | 3440 independent reflections |
Radiation source: Fine-focus sealed tube | 2741 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.053 |
φ and ω scans | θmax = 26.8°, θmin = 0.9° |
Absorption correction: multi-scan SADABS | h = −11→11 |
Tmin = 0.89, Tmax = 0.96 | k = −9→10 |
44653 measured reflections | l = −53→54 |
Refinement top
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)] = 0.038 | Hydrogen site location: mixed |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0435P)2 + 2.0184P] where P = (Fo2 + 2Fc2)/3 |
3440 reflections | (Δ/σ)max = 0.001 |
227 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.61043 (16) | 0.5662 (2) | 0.37679 (3) | 0.0204 (3) | |
H1 | 0.707 (3) | 0.574 (3) | 0.3806 (6) | 0.050 (7)* | |
C2 | 0.56235 (18) | 0.4826 (2) | 0.35244 (4) | 0.0220 (4) | |
H2 | 0.6295 | 0.4294 | 0.3395 | 0.026* | |
N3 | 0.42816 (15) | 0.4677 (2) | 0.34488 (3) | 0.0216 (3) | |
C4 | 0.33158 (18) | 0.5386 (2) | 0.36391 (4) | 0.0191 (4) | |
C5 | 0.27757 (18) | 0.6876 (2) | 0.41456 (4) | 0.0191 (4) | |
H5 | 0.179 | 0.677 | 0.4116 | 0.023* | |
C6 | 0.32851 (18) | 0.7690 (2) | 0.44030 (4) | 0.0189 (4) | |
C7 | 0.47767 (18) | 0.7891 (2) | 0.44460 (4) | 0.0193 (4) | |
C8 | 0.57063 (17) | 0.7212 (2) | 0.42374 (4) | 0.0191 (4) | |
H8 | 0.6692 | 0.7325 | 0.4267 | 0.023* | |
C9 | 0.51783 (18) | 0.6349 (2) | 0.39794 (4) | 0.0184 (4) | |
C10 | 0.37196 (18) | 0.6196 (2) | 0.39250 (4) | 0.0183 (4) | |
H11 | 0.131 (2) | 0.568 (3) | 0.3676 (5) | 0.034 (6)* | |
N11 | 0.19569 (16) | 0.5314 (2) | 0.35527 (3) | 0.0210 (3) | |
C12 | 0.14402 (18) | 0.4718 (2) | 0.32624 (4) | 0.0198 (4) | |
C13 | 0.01653 (18) | 0.3863 (2) | 0.32640 (4) | 0.0197 (4) | |
H13 | −0.0294 | 0.3637 | 0.3455 | 0.024* | |
C14 | −0.04463 (19) | 0.3332 (2) | 0.29848 (4) | 0.0213 (4) | |
C15 | 0.0252 (2) | 0.3641 (3) | 0.27057 (4) | 0.0257 (4) | |
H15 | −0.0135 | 0.3253 | 0.2516 | 0.031* | |
C16 | 0.1514 (2) | 0.4520 (3) | 0.27069 (4) | 0.0281 (4) | |
H16 | 0.1976 | 0.4744 | 0.2517 | 0.034* | |
C17 | 0.21101 (19) | 0.5075 (3) | 0.29817 (4) | 0.0252 (4) | |
H17 | 0.2964 | 0.5692 | 0.2979 | 0.03* | |
C18 | −0.1822 (2) | 0.2567 (2) | 0.29888 (4) | 0.0237 (4) | |
C19 | −0.2992 (2) | 0.2029 (3) | 0.29934 (5) | 0.0293 (5) | |
H19 | −0.3924 | 0.1601 | 0.2997 | 0.035* | |
O20 | 0.24816 (13) | 0.83706 (17) | 0.46320 (3) | 0.0242 (3) | |
C21 | 0.09758 (18) | 0.8180 (3) | 0.46041 (4) | 0.0264 (4) | |
H21A | 0.0656 | 0.8705 | 0.4412 | 0.04* | |
H21B | 0.0513 | 0.8718 | 0.478 | 0.04* | |
H21C | 0.0737 | 0.6988 | 0.4601 | 0.04* | |
O22 | 0.51524 (13) | 0.87877 (17) | 0.46991 (3) | 0.0245 (3) | |
C23 | 0.66261 (19) | 0.9183 (3) | 0.47316 (4) | 0.0277 (4) | |
H23A | 0.7163 | 0.8149 | 0.476 | 0.042* | |
H23B | 0.676 | 0.9912 | 0.4911 | 0.042* | |
H23C | 0.6956 | 0.9758 | 0.4545 | 0.042* | |
Cl24 | 0.91894 (4) | 0.63367 (6) | 0.39344 (2) | 0.02598 (15) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0155 (7) | 0.0237 (8) | 0.0221 (8) | 0.0010 (7) | 0.0004 (6) | −0.0015 (7) |
C2 | 0.0212 (9) | 0.0226 (9) | 0.0222 (9) | 0.0020 (8) | 0.0018 (7) | −0.0002 (8) |
N3 | 0.0194 (8) | 0.0231 (8) | 0.0225 (8) | 0.0022 (7) | −0.0008 (6) | −0.0018 (7) |
C4 | 0.0180 (8) | 0.0190 (9) | 0.0203 (9) | −0.0012 (7) | 0.0005 (7) | 0.0028 (8) |
C5 | 0.0151 (8) | 0.0214 (9) | 0.0207 (8) | −0.0005 (7) | −0.0012 (7) | 0.0012 (8) |
C6 | 0.0189 (8) | 0.0200 (9) | 0.0179 (8) | 0.0006 (8) | 0.0019 (7) | 0.0017 (8) |
C7 | 0.0217 (9) | 0.0193 (9) | 0.0169 (8) | −0.0016 (8) | −0.0033 (7) | 0.0001 (8) |
C8 | 0.0149 (8) | 0.0206 (9) | 0.0218 (9) | −0.0017 (7) | −0.0027 (7) | 0.0014 (8) |
C9 | 0.0181 (8) | 0.0176 (9) | 0.0194 (8) | 0.0006 (7) | 0.0018 (7) | 0.0039 (8) |
C10 | 0.0188 (9) | 0.0170 (9) | 0.0190 (8) | 0.0001 (7) | −0.0008 (7) | 0.0018 (7) |
N11 | 0.0163 (7) | 0.0289 (9) | 0.0178 (7) | −0.0004 (7) | −0.0011 (6) | −0.0026 (7) |
C12 | 0.0199 (9) | 0.0212 (9) | 0.0182 (8) | 0.0017 (8) | −0.0033 (7) | −0.0009 (8) |
C13 | 0.0201 (9) | 0.0208 (9) | 0.0182 (8) | 0.0008 (8) | −0.0002 (7) | 0.0010 (8) |
C14 | 0.0212 (9) | 0.0193 (9) | 0.0235 (9) | 0.0012 (8) | −0.0031 (7) | −0.0013 (8) |
C15 | 0.0252 (9) | 0.0333 (11) | 0.0186 (9) | 0.0014 (9) | −0.0034 (7) | −0.0043 (9) |
C16 | 0.0269 (10) | 0.0365 (11) | 0.0208 (9) | −0.0006 (9) | 0.0030 (8) | 0.0007 (9) |
C17 | 0.0199 (9) | 0.0317 (11) | 0.0240 (9) | −0.0037 (8) | 0.0000 (7) | 0.0016 (9) |
C18 | 0.0303 (10) | 0.0214 (9) | 0.0193 (9) | 0.0010 (9) | −0.0046 (7) | −0.0029 (8) |
C19 | 0.0274 (10) | 0.0277 (10) | 0.0328 (11) | −0.0067 (9) | −0.0035 (8) | −0.0027 (9) |
O20 | 0.0184 (6) | 0.0321 (7) | 0.0221 (6) | 0.0007 (6) | 0.0023 (5) | −0.0066 (6) |
C21 | 0.0178 (9) | 0.0347 (11) | 0.0268 (9) | 0.0017 (8) | 0.0036 (7) | −0.0024 (9) |
O22 | 0.0202 (6) | 0.0310 (7) | 0.0224 (7) | −0.0034 (6) | −0.0022 (5) | −0.0051 (6) |
C23 | 0.0208 (9) | 0.0352 (11) | 0.0271 (10) | −0.0058 (9) | −0.0036 (8) | −0.0062 (9) |
Cl24 | 0.0149 (2) | 0.0340 (3) | 0.0290 (3) | −0.00064 (19) | −0.00027 (17) | −0.0003 (2) |
Geometric parameters (Å, º) top
N1—C2 | 1.329 (2) | C12—C17 | 1.401 (2) |
N1—C9 | 1.384 (2) | C13—C14 | 1.406 (2) |
N1—H1 | 0.94 (3) | C13—H13 | 0.95 |
C2—N3 | 1.322 (2) | C14—C15 | 1.400 (3) |
C2—H2 | 0.95 | C14—C18 | 1.444 (3) |
N3—C4 | 1.357 (2) | C15—C16 | 1.390 (3) |
C4—N11 | 1.346 (2) | C15—H15 | 0.95 |
C4—C10 | 1.448 (2) | C16—C17 | 1.390 (3) |
C5—C6 | 1.378 (2) | C16—H16 | 0.95 |
C5—C10 | 1.418 (2) | C17—H17 | 0.95 |
C5—H5 | 0.95 | C18—C19 | 1.193 (3) |
C6—O20 | 1.364 (2) | C19—H19 | 0.95 |
C6—C7 | 1.439 (2) | O20—C21 | 1.445 (2) |
C7—O22 | 1.356 (2) | C21—H21A | 0.98 |
C7—C8 | 1.375 (2) | C21—H21B | 0.98 |
C8—C9 | 1.405 (2) | C21—H21C | 0.98 |
C8—H8 | 0.95 | O22—C23 | 1.443 (2) |
C9—C10 | 1.412 (2) | C23—H23A | 0.98 |
N11—C12 | 1.430 (2) | C23—H23B | 0.98 |
N11—H11 | 0.87 (2) | C23—H23C | 0.98 |
C12—C13 | 1.392 (3) | | |
| | | |
C2—N1—C9 | 120.35 (16) | C17—C12—N11 | 122.50 (16) |
C2—N1—H1 | 120.6 (15) | C12—C13—C14 | 120.28 (16) |
C9—N1—H1 | 118.9 (15) | C12—C13—H13 | 119.9 |
N3—C2—N1 | 124.98 (17) | C14—C13—H13 | 119.9 |
N3—C2—H2 | 117.5 | C15—C14—C13 | 119.42 (17) |
N1—C2—H2 | 117.5 | C15—C14—C18 | 120.98 (16) |
C2—N3—C4 | 117.71 (15) | C13—C14—C18 | 119.49 (16) |
N11—C4—N3 | 117.59 (16) | C16—C15—C14 | 119.70 (17) |
N11—C4—C10 | 120.70 (16) | C16—C15—H15 | 120.2 |
N3—C4—C10 | 121.71 (16) | C14—C15—H15 | 120.2 |
C6—C5—C10 | 120.16 (16) | C15—C16—C17 | 121.11 (17) |
C6—C5—H5 | 119.9 | C15—C16—H16 | 119.4 |
C10—C5—H5 | 119.9 | C17—C16—H16 | 119.4 |
O20—C6—C5 | 125.35 (16) | C16—C17—C12 | 119.39 (17) |
O20—C6—C7 | 114.39 (15) | C16—C17—H17 | 120.3 |
C5—C6—C7 | 120.25 (15) | C12—C17—H17 | 120.3 |
O22—C7—C8 | 124.71 (16) | C19—C18—C14 | 176.1 (2) |
O22—C7—C6 | 115.02 (15) | C18—C19—H19 | 180.0 |
C8—C7—C6 | 120.27 (16) | C6—O20—C21 | 116.87 (14) |
C7—C8—C9 | 119.07 (16) | O20—C21—H21A | 109.5 |
C7—C8—H8 | 120.5 | O20—C21—H21B | 109.5 |
C9—C8—H8 | 120.5 | H21A—C21—H21B | 109.5 |
N1—C9—C8 | 119.55 (16) | O20—C21—H21C | 109.5 |
N1—C9—C10 | 118.71 (16) | H21A—C21—H21C | 109.5 |
C8—C9—C10 | 121.72 (16) | H21B—C21—H21C | 109.5 |
C9—C10—C5 | 118.44 (16) | C7—O22—C23 | 116.74 (14) |
C9—C10—C4 | 116.19 (15) | O22—C23—H23A | 109.5 |
C5—C10—C4 | 125.34 (16) | O22—C23—H23B | 109.5 |
C4—N11—C12 | 125.98 (16) | H23A—C23—H23B | 109.5 |
C4—N11—H11 | 120.0 (15) | O22—C23—H23C | 109.5 |
C12—N11—H11 | 114.0 (15) | H23A—C23—H23C | 109.5 |
C13—C12—C17 | 120.04 (16) | H23B—C23—H23C | 109.5 |
C13—C12—N11 | 117.28 (15) | | |
| | | |
C9—N1—C2—N3 | 5.3 (3) | N11—C4—C10—C9 | −173.99 (16) |
N1—C2—N3—C4 | −2.2 (3) | N3—C4—C10—C9 | 5.9 (3) |
C2—N3—C4—N11 | 176.37 (17) | N11—C4—C10—C5 | 4.2 (3) |
C2—N3—C4—C10 | −3.5 (3) | N3—C4—C10—C5 | −175.95 (17) |
C10—C5—C6—O20 | −179.04 (17) | N3—C4—N11—C12 | −7.2 (3) |
C10—C5—C6—C7 | 1.5 (3) | C10—C4—N11—C12 | 172.68 (17) |
O20—C6—C7—O22 | −2.8 (2) | C4—N11—C12—C13 | 144.60 (18) |
C5—C6—C7—O22 | 176.68 (16) | C4—N11—C12—C17 | −40.3 (3) |
O20—C6—C7—C8 | 177.74 (16) | C17—C12—C13—C14 | 0.9 (3) |
C5—C6—C7—C8 | −2.8 (3) | N11—C12—C13—C14 | 176.14 (16) |
O22—C7—C8—C9 | −178.21 (16) | C12—C13—C14—C15 | 1.2 (3) |
C6—C7—C8—C9 | 1.2 (3) | C12—C13—C14—C18 | −175.01 (17) |
C2—N1—C9—C8 | 179.27 (16) | C13—C14—C15—C16 | −2.2 (3) |
C2—N1—C9—C10 | −2.3 (3) | C18—C14—C15—C16 | 173.96 (18) |
C7—C8—C9—N1 | 179.93 (16) | C14—C15—C16—C17 | 1.1 (3) |
C7—C8—C9—C10 | 1.6 (3) | C15—C16—C17—C12 | 1.1 (3) |
N1—C9—C10—C5 | 178.86 (16) | C13—C12—C17—C16 | −2.1 (3) |
C8—C9—C10—C5 | −2.8 (3) | N11—C12—C17—C16 | −177.07 (18) |
N1—C9—C10—C4 | −2.8 (2) | C5—C6—O20—C21 | 1.6 (3) |
C8—C9—C10—C4 | 175.50 (16) | C7—C6—O20—C21 | −178.90 (16) |
C6—C5—C10—C9 | 1.2 (3) | C8—C7—O22—C23 | 6.3 (3) |
C6—C5—C10—C4 | −176.94 (17) | C6—C7—O22—C23 | −173.08 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Cl24 | 0.94 (3) | 2.14 (3) | 3.0681 (17) | 169 (2) |
N11—H11···Cl24i | 0.87 (2) | 2.36 (2) | 3.2121 (17) | 167 (2) |
Symmetry code: (i) x−1, y, z. |
Crystal data top
2(C18H16N3O2)·C6H8O4·C6H10O4·CH4O | Z = 2 |
Mr = 934.98 | F(000) = 988 |
Triclinic, P1 | Dx = 1.393 Mg m−3 |
a = 9.304 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 15.756 (8) Å | Cell parameters from 3033 reflections |
c = 15.829 (7) Å | θ = 2.3–24.9° |
α = 94.54 (2)° | µ = 0.10 mm−1 |
β = 93.95 (2)° | T = 130 K |
γ = 104.56 (2)° | Blocks, colourless |
V = 2229.4 (18) Å3 | 0.44 × 0.30 × 0.17 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 8806 independent reflections |
Radiation source: Fine-focus sealed tube | 4654 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.115 |
φ and ω scans | θmax = 26.6°, θmin = 1.3° |
Absorption correction: multi-scan SADABS | h = −11→11 |
Tmin = 0.96, Tmax = 0.98 | k = −19→19 |
35562 measured reflections | l = −19→19 |
Refinement top
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)] = 0.065 | Hydrogen site location: mixed |
wR(F2) = 0.198 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0887P)2] where P = (Fo2 + 2Fc2)/3 |
8806 reflections | (Δ/σ)max = 0.001 |
646 parameters | Δρmax = 0.48 e Å−3 |
5 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.6662 (3) | 0.18681 (18) | 0.77454 (17) | 0.0233 (7) | |
H1 | 0.681 (5) | 0.193 (3) | 0.715 (2) | 0.057 (13)* | |
C2 | 0.5454 (4) | 0.1311 (2) | 0.7921 (2) | 0.0252 (8) | |
H2 | 0.4819 | 0.0967 | 0.7455 | 0.03* | |
N3 | 0.5035 (3) | 0.11826 (18) | 0.86899 (17) | 0.0243 (7) | |
C4 | 0.5897 (4) | 0.1676 (2) | 0.9349 (2) | 0.0210 (8) | |
C5 | 0.8181 (4) | 0.2863 (2) | 0.9882 (2) | 0.0226 (8) | |
H5 | 0.7956 | 0.2825 | 1.0457 | 0.027* | |
C6 | 0.9428 (4) | 0.3442 (2) | 0.9699 (2) | 0.0219 (8) | |
C7 | 0.9787 (4) | 0.3497 (2) | 0.8842 (2) | 0.0205 (8) | |
C8 | 0.8884 (4) | 0.2977 (2) | 0.8198 (2) | 0.0227 (8) | |
H8 | 0.9126 | 0.301 | 0.7626 | 0.027* | |
C9 | 0.7594 (4) | 0.2393 (2) | 0.83913 (19) | 0.0198 (8) | |
C10 | 0.7218 (4) | 0.2315 (2) | 0.92261 (19) | 0.0204 (8) | |
H11 | 0.607 (4) | 0.193 (3) | 1.058 (2) | 0.044 (12)* | |
N11 | 0.5492 (3) | 0.15582 (19) | 1.01379 (18) | 0.0245 (7) | |
C12 | 0.4287 (4) | 0.0953 (2) | 1.0418 (2) | 0.0232 (8) | |
C13 | 0.4316 (4) | 0.0930 (2) | 1.1295 (2) | 0.0245 (8) | |
H13 | 0.5123 | 0.1309 | 1.1652 | 0.029* | |
C14 | 0.3195 (4) | 0.0365 (2) | 1.1658 (2) | 0.0293 (9) | |
C15 | 0.2024 (4) | −0.0179 (2) | 1.1132 (2) | 0.0336 (9) | |
H15 | 0.1231 | −0.0568 | 1.1366 | 0.04* | |
C16 | 0.2021 (5) | −0.0150 (2) | 1.0272 (2) | 0.0380 (10) | |
H16 | 0.1216 | −0.0527 | 0.9912 | 0.046* | |
C17 | 0.3136 (4) | 0.0402 (2) | 0.9912 (2) | 0.0341 (9) | |
H17 | 0.3108 | 0.0402 | 0.931 | 0.041* | |
C18 | 0.3309 (4) | 0.0337 (2) | 1.2559 (2) | 0.0354 (10) | |
C19 | 0.3483 (5) | 0.0289 (3) | 1.3293 (3) | 0.0509 (12) | |
H19 | 0.3624 | 0.025 | 1.3888 | 0.061* | |
O20 | 1.0398 (3) | 0.40036 (15) | 1.02769 (13) | 0.0277 (6) | |
C21 | 0.9977 (4) | 0.4064 (2) | 1.1127 (2) | 0.0280 (9) | |
H21A | 0.902 | 0.4217 | 1.1125 | 0.042* | |
H21B | 1.0741 | 0.4519 | 1.1482 | 0.042* | |
H21C | 0.9882 | 0.3495 | 1.1359 | 0.042* | |
O22 | 1.1057 (3) | 0.40882 (15) | 0.87362 (13) | 0.0254 (6) | |
C23 | 1.1396 (4) | 0.4219 (2) | 0.7875 (2) | 0.0281 (9) | |
H23A | 1.1443 | 0.3659 | 0.7577 | 0.042* | |
H23B | 1.2359 | 0.4653 | 0.788 | 0.042* | |
H23C | 1.0615 | 0.4435 | 0.7583 | 0.042* | |
H24 | 0.568 (5) | 0.402 (3) | 1.073 (2) | 0.066 (14)* | |
N24 | 0.5623 (3) | 0.40509 (19) | 1.01208 (18) | 0.0260 (7) | |
C25 | 0.6648 (4) | 0.4553 (2) | 0.9720 (2) | 0.0265 (8) | |
H25 | 0.7459 | 0.4951 | 1.0059 | 0.032* | |
N26 | 0.6648 (3) | 0.45541 (18) | 0.88867 (17) | 0.0254 (7) | |
C27 | 0.5539 (4) | 0.3985 (2) | 0.8411 (2) | 0.0229 (8) | |
C28 | 0.3248 (4) | 0.2740 (2) | 0.8317 (2) | 0.0242 (8) | |
H28 | 0.3203 | 0.2664 | 0.7713 | 0.029* | |
C29 | 0.2198 (4) | 0.2218 (2) | 0.8727 (2) | 0.0225 (8) | |
C30 | 0.2230 (4) | 0.2338 (2) | 0.9627 (2) | 0.0231 (8) | |
C31 | 0.3362 (4) | 0.2940 (2) | 1.0082 (2) | 0.0246 (8) | |
H31 | 0.3411 | 0.3005 | 1.0686 | 0.03* | |
C32 | 0.4453 (4) | 0.3460 (2) | 0.9661 (2) | 0.0219 (8) | |
C33 | 0.4396 (4) | 0.3389 (2) | 0.8773 (2) | 0.0223 (8) | |
H34 | 0.485 (4) | 0.360 (2) | 0.724 (2) | 0.028 (10)* | |
N34 | 0.5571 (3) | 0.39817 (19) | 0.75652 (18) | 0.0249 (7) | |
C35 | 0.6682 (4) | 0.4573 (2) | 0.7176 (2) | 0.0242 (8) | |
C36 | 0.6774 (4) | 0.5464 (2) | 0.7279 (2) | 0.0261 (8) | |
H36 | 0.6111 | 0.5683 | 0.7613 | 0.031* | |
C37 | 0.7850 (4) | 0.6032 (2) | 0.6886 (2) | 0.0280 (9) | |
C38 | 0.8813 (4) | 0.5702 (2) | 0.6406 (2) | 0.0313 (9) | |
H38 | 0.9562 | 0.6095 | 0.6145 | 0.038* | |
C39 | 0.8697 (4) | 0.4824 (2) | 0.6304 (2) | 0.0310 (9) | |
H39 | 0.9358 | 0.4603 | 0.5969 | 0.037* | |
C40 | 0.7618 (4) | 0.4252 (2) | 0.6686 (2) | 0.0277 (9) | |
H40 | 0.7526 | 0.3636 | 0.661 | 0.033* | |
C41 | 0.7927 (5) | 0.6952 (3) | 0.6962 (2) | 0.0396 (11) | |
C42 | 0.7942 (6) | 0.7694 (3) | 0.7012 (3) | 0.0616 (15) | |
H42 | 0.7954 | 0.8301 | 0.7052 | 0.074* | |
O43 | 0.1059 (3) | 0.15688 (15) | 0.83480 (14) | 0.0278 (6) | |
C44 | 0.0984 (4) | 0.1412 (2) | 0.7442 (2) | 0.0324 (9) | |
H44A | 0.0925 | 0.195 | 0.7186 | 0.049* | |
H44B | 0.0097 | 0.0937 | 0.7237 | 0.049* | |
H44C | 0.1879 | 0.1242 | 0.7281 | 0.049* | |
O45 | 0.1087 (3) | 0.18256 (15) | 0.99632 (14) | 0.0297 (6) | |
C46 | 0.1123 (4) | 0.1918 (2) | 1.0869 (2) | 0.0334 (9) | |
H46A | 0.193 | 0.1691 | 1.1115 | 0.05* | |
H46B | 0.0169 | 0.1585 | 1.1042 | 0.05* | |
H46C | 0.1294 | 0.2542 | 1.1074 | 0.05* | |
O47 | 0.9328 (3) | 0.26142 (16) | 0.60987 (14) | 0.0298 (6) | |
O48 | 0.6959 (3) | 0.19518 (16) | 0.60562 (14) | 0.0307 (6) | |
C49 | 0.8127 (4) | 0.2235 (2) | 0.5699 (2) | 0.0241 (8) | |
C50 | 0.8003 (4) | 0.2123 (2) | 0.47383 (19) | 0.0256 (8) | |
H50A | 0.7339 | 0.1536 | 0.4531 | 0.031* | |
H50B | 0.8999 | 0.2151 | 0.4542 | 0.031* | |
C51 | 0.7384 (4) | 0.2837 (2) | 0.4365 (2) | 0.0270 (9) | |
H51A | 0.6403 | 0.282 | 0.4579 | 0.032* | |
H51B | 0.8064 | 0.3421 | 0.4563 | 0.032* | |
C52 | 0.7203 (4) | 0.2727 (2) | 0.34023 (19) | 0.0265 (8) | |
H52A | 0.8182 | 0.2735 | 0.3189 | 0.032* | |
H52B | 0.6513 | 0.2145 | 0.3206 | 0.032* | |
C53 | 0.6612 (4) | 0.3433 (2) | 0.3027 (2) | 0.0312 (9) | |
H53A | 0.7299 | 0.4012 | 0.3235 | 0.037* | |
H53B | 0.5635 | 0.342 | 0.3244 | 0.037* | |
C54 | 0.6418 (4) | 0.3363 (2) | 0.2067 (2) | 0.0241 (8) | |
O55 | 0.5912 (3) | 0.39546 (16) | 0.17526 (14) | 0.0295 (6) | |
O56 | 0.6743 (3) | 0.27537 (15) | 0.16538 (14) | 0.0310 (6) | |
H57 | 0.916 (5) | 0.696 (3) | 0.439 (3) | 0.09 (2)* | |
O57 | 0.8451 (3) | 0.66976 (18) | 0.46871 (16) | 0.0376 (7) | |
O58 | 0.6968 (3) | 0.68517 (17) | 0.36078 (15) | 0.0359 (7) | |
C59 | 0.7146 (4) | 0.6617 (2) | 0.4309 (2) | 0.0263 (8) | |
C60 | 0.5907 (4) | 0.6203 (2) | 0.4806 (2) | 0.0258 (8) | |
H60A | 0.4981 | 0.6342 | 0.4582 | 0.031* | |
H60B | 0.6136 | 0.6457 | 0.5407 | 0.031* | |
C61 | 0.5654 (4) | 0.5210 (2) | 0.4765 (2) | 0.0247 (8) | |
H61A | 0.5474 | 0.4959 | 0.4162 | 0.03* | |
H61B | 0.6563 | 0.5072 | 0.5015 | 0.03* | |
H62 | 0.479 (4) | 0.833 (3) | 0.445 (3) | 0.077 (17)* | |
O62 | 0.5681 (3) | 0.83802 (19) | 0.47393 (17) | 0.0425 (7) | |
O63 | 0.6431 (3) | 0.9375 (2) | 0.3863 (2) | 0.0609 (10) | |
C64 | 0.6705 (4) | 0.8968 (2) | 0.4431 (2) | 0.0317 (9) | |
C65 | 0.8222 (4) | 0.9052 (2) | 0.4820 (2) | 0.0304 (9) | |
H65A | 0.8664 | 0.8628 | 0.4503 | 0.037* | |
H65B | 0.8168 | 0.8897 | 0.5413 | 0.037* | |
C66 | 0.9216 (4) | 0.9964 (2) | 0.4823 (2) | 0.0325 (9) | |
H66A | 0.8804 | 1.0384 | 0.5166 | 0.039* | |
H66B | 0.9228 | 1.0132 | 0.4233 | 0.039* | |
C67 | 0.8009 (6) | 0.0793 (3) | 0.2371 (3) | 0.0607 (14) | |
H67A | 0.8625 | 0.1104 | 0.2884 | 0.091* | |
H67B | 0.8379 | 0.029 | 0.2171 | 0.091* | |
H67C | 0.6973 | 0.0583 | 0.2502 | 0.091* | |
H68 | 0.768 (9) | 0.180 (4) | 0.192 (5) | 0.22 (4)* | |
O68 | 0.8081 (4) | 0.1374 (2) | 0.17298 (18) | 0.0526 (8) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0260 (19) | 0.0235 (16) | 0.0186 (15) | 0.0027 (14) | 0.0029 (13) | 0.0018 (12) |
C2 | 0.026 (2) | 0.0267 (19) | 0.0210 (18) | 0.0036 (17) | 0.0006 (16) | −0.0004 (15) |
N3 | 0.0247 (19) | 0.0251 (16) | 0.0215 (15) | 0.0035 (14) | 0.0013 (13) | 0.0033 (12) |
C4 | 0.021 (2) | 0.0205 (18) | 0.0211 (18) | 0.0035 (16) | 0.0045 (15) | 0.0034 (14) |
C5 | 0.026 (2) | 0.0228 (18) | 0.0189 (17) | 0.0054 (17) | 0.0061 (15) | 0.0021 (14) |
C6 | 0.024 (2) | 0.0215 (18) | 0.0184 (17) | 0.0042 (16) | 0.0003 (15) | 0.0015 (14) |
C7 | 0.019 (2) | 0.0176 (17) | 0.0234 (18) | −0.0003 (16) | 0.0061 (15) | 0.0053 (14) |
C8 | 0.030 (2) | 0.0208 (18) | 0.0179 (17) | 0.0064 (16) | 0.0047 (15) | 0.0050 (14) |
C9 | 0.022 (2) | 0.0170 (17) | 0.0190 (17) | 0.0024 (15) | 0.0024 (15) | 0.0017 (13) |
C10 | 0.022 (2) | 0.0189 (17) | 0.0193 (17) | 0.0039 (16) | 0.0037 (15) | 0.0020 (13) |
N11 | 0.025 (2) | 0.0249 (16) | 0.0205 (15) | 0.0011 (14) | 0.0022 (14) | 0.0044 (13) |
C12 | 0.021 (2) | 0.0211 (18) | 0.0262 (18) | 0.0011 (16) | 0.0070 (16) | 0.0037 (14) |
C13 | 0.022 (2) | 0.0256 (19) | 0.0267 (19) | 0.0052 (16) | 0.0067 (16) | 0.0052 (15) |
C14 | 0.035 (3) | 0.029 (2) | 0.027 (2) | 0.0095 (19) | 0.0148 (17) | 0.0099 (16) |
C15 | 0.029 (3) | 0.028 (2) | 0.040 (2) | −0.0013 (18) | 0.0125 (19) | 0.0041 (17) |
C16 | 0.034 (3) | 0.034 (2) | 0.036 (2) | −0.009 (2) | 0.0082 (19) | −0.0026 (17) |
C17 | 0.029 (3) | 0.039 (2) | 0.028 (2) | −0.0021 (19) | 0.0035 (18) | 0.0031 (17) |
C18 | 0.037 (3) | 0.033 (2) | 0.036 (2) | 0.0061 (19) | 0.0116 (19) | 0.0075 (17) |
C19 | 0.062 (3) | 0.058 (3) | 0.036 (2) | 0.017 (3) | 0.013 (2) | 0.011 (2) |
O20 | 0.0254 (16) | 0.0333 (14) | 0.0173 (12) | −0.0036 (12) | 0.0011 (11) | −0.0023 (10) |
C21 | 0.030 (2) | 0.031 (2) | 0.0194 (18) | 0.0015 (18) | 0.0032 (16) | −0.0029 (15) |
O22 | 0.0267 (16) | 0.0275 (13) | 0.0197 (12) | 0.0008 (12) | 0.0070 (11) | 0.0048 (10) |
C23 | 0.029 (2) | 0.033 (2) | 0.0214 (18) | 0.0046 (18) | 0.0090 (16) | 0.0078 (15) |
N24 | 0.028 (2) | 0.0273 (17) | 0.0212 (16) | 0.0045 (15) | 0.0009 (14) | 0.0053 (13) |
C25 | 0.025 (2) | 0.0251 (19) | 0.0263 (19) | 0.0015 (17) | −0.0006 (16) | 0.0043 (15) |
N26 | 0.0237 (19) | 0.0274 (16) | 0.0215 (15) | 0.0000 (14) | −0.0016 (13) | 0.0048 (12) |
C27 | 0.024 (2) | 0.0244 (18) | 0.0204 (17) | 0.0047 (17) | 0.0019 (15) | 0.0059 (14) |
C28 | 0.024 (2) | 0.0258 (19) | 0.0223 (18) | 0.0049 (17) | 0.0018 (16) | 0.0048 (15) |
C29 | 0.019 (2) | 0.0213 (18) | 0.0258 (18) | 0.0017 (16) | 0.0019 (15) | 0.0064 (14) |
C30 | 0.020 (2) | 0.0257 (19) | 0.0246 (18) | 0.0037 (16) | 0.0076 (16) | 0.0105 (15) |
C31 | 0.025 (2) | 0.030 (2) | 0.0192 (17) | 0.0071 (17) | 0.0029 (16) | 0.0067 (15) |
C32 | 0.023 (2) | 0.0216 (18) | 0.0208 (17) | 0.0057 (16) | −0.0006 (15) | 0.0048 (14) |
C33 | 0.022 (2) | 0.0213 (18) | 0.0235 (18) | 0.0048 (16) | 0.0017 (15) | 0.0067 (14) |
N34 | 0.0205 (19) | 0.0272 (17) | 0.0212 (16) | −0.0054 (14) | 0.0019 (14) | 0.0046 (13) |
C35 | 0.024 (2) | 0.0270 (19) | 0.0183 (17) | 0.0014 (17) | −0.0006 (15) | 0.0038 (14) |
C36 | 0.026 (2) | 0.030 (2) | 0.0192 (17) | 0.0016 (17) | 0.0011 (15) | 0.0043 (15) |
C37 | 0.030 (2) | 0.027 (2) | 0.0227 (18) | 0.0021 (18) | −0.0043 (17) | 0.0028 (15) |
C38 | 0.026 (2) | 0.038 (2) | 0.0241 (19) | −0.0044 (18) | −0.0002 (17) | 0.0119 (16) |
C39 | 0.024 (2) | 0.041 (2) | 0.0268 (19) | 0.0031 (18) | 0.0041 (16) | 0.0117 (17) |
C40 | 0.028 (2) | 0.030 (2) | 0.0252 (18) | 0.0056 (18) | 0.0032 (16) | 0.0064 (15) |
C41 | 0.053 (3) | 0.034 (2) | 0.025 (2) | −0.002 (2) | 0.0018 (19) | 0.0046 (17) |
C42 | 0.110 (5) | 0.034 (3) | 0.039 (3) | 0.014 (3) | 0.006 (3) | 0.006 (2) |
O43 | 0.0275 (16) | 0.0280 (14) | 0.0224 (12) | −0.0041 (12) | 0.0038 (11) | 0.0045 (10) |
C44 | 0.037 (3) | 0.031 (2) | 0.0229 (19) | −0.0014 (19) | 0.0018 (17) | 0.0010 (15) |
O45 | 0.0292 (16) | 0.0337 (14) | 0.0237 (13) | 0.0002 (12) | 0.0069 (11) | 0.0097 (11) |
C46 | 0.035 (3) | 0.041 (2) | 0.0226 (19) | 0.0009 (19) | 0.0123 (17) | 0.0097 (16) |
O47 | 0.0238 (16) | 0.0389 (15) | 0.0216 (13) | −0.0021 (12) | −0.0002 (11) | 0.0086 (11) |
O48 | 0.0214 (16) | 0.0444 (16) | 0.0207 (13) | −0.0034 (12) | 0.0040 (11) | 0.0076 (11) |
C49 | 0.026 (2) | 0.0245 (19) | 0.0190 (18) | 0.0006 (17) | 0.0010 (17) | 0.0044 (14) |
C50 | 0.029 (2) | 0.029 (2) | 0.0178 (17) | 0.0064 (17) | 0.0015 (15) | 0.0028 (14) |
C51 | 0.032 (2) | 0.029 (2) | 0.0197 (18) | 0.0061 (17) | 0.0042 (16) | 0.0019 (14) |
C52 | 0.031 (2) | 0.031 (2) | 0.0181 (17) | 0.0080 (17) | 0.0042 (16) | 0.0016 (14) |
C53 | 0.041 (3) | 0.034 (2) | 0.0191 (18) | 0.0103 (19) | 0.0035 (17) | 0.0031 (15) |
C54 | 0.024 (2) | 0.027 (2) | 0.0162 (17) | −0.0043 (17) | 0.0024 (15) | 0.0029 (15) |
O55 | 0.0338 (17) | 0.0350 (14) | 0.0199 (12) | 0.0081 (13) | 0.0018 (11) | 0.0074 (10) |
O56 | 0.0404 (18) | 0.0290 (14) | 0.0212 (13) | 0.0045 (13) | 0.0043 (12) | 0.0015 (11) |
O57 | 0.0248 (18) | 0.0530 (18) | 0.0310 (15) | −0.0019 (14) | 0.0027 (13) | 0.0181 (13) |
O58 | 0.0298 (17) | 0.0485 (17) | 0.0236 (14) | −0.0026 (13) | 0.0008 (11) | 0.0113 (12) |
C59 | 0.025 (2) | 0.0269 (19) | 0.0227 (19) | 0.0005 (17) | −0.0014 (16) | 0.0017 (15) |
C60 | 0.025 (2) | 0.029 (2) | 0.0213 (18) | −0.0003 (17) | 0.0045 (16) | 0.0058 (15) |
C61 | 0.021 (2) | 0.0270 (19) | 0.0234 (18) | −0.0010 (16) | 0.0026 (15) | 0.0075 (14) |
O62 | 0.0279 (19) | 0.0521 (18) | 0.0410 (16) | −0.0042 (15) | −0.0016 (14) | 0.0169 (13) |
O63 | 0.033 (2) | 0.074 (2) | 0.066 (2) | −0.0120 (16) | −0.0105 (16) | 0.0406 (18) |
C64 | 0.029 (3) | 0.031 (2) | 0.029 (2) | −0.0043 (19) | 0.0041 (18) | 0.0055 (17) |
C65 | 0.026 (2) | 0.033 (2) | 0.028 (2) | 0.0015 (18) | −0.0004 (17) | 0.0037 (16) |
C66 | 0.029 (2) | 0.031 (2) | 0.034 (2) | 0.0025 (19) | 0.0005 (18) | 0.0054 (17) |
C67 | 0.085 (4) | 0.049 (3) | 0.051 (3) | 0.025 (3) | −0.004 (3) | 0.008 (2) |
O68 | 0.055 (2) | 0.064 (2) | 0.0421 (17) | 0.0155 (18) | 0.0166 (15) | 0.0096 (15) |
Geometric parameters (Å, º) top
N1—C2 | 1.303 (4) | C35—C36 | 1.380 (5) |
N1—C9 | 1.365 (4) | C36—C37 | 1.383 (5) |
N1—H1 | 0.97 (3) | C36—H36 | 0.95 |
C2—N3 | 1.318 (4) | C37—C38 | 1.384 (5) |
C2—H2 | 0.95 | C37—C41 | 1.428 (5) |
N3—C4 | 1.333 (4) | C38—C39 | 1.357 (5) |
C4—N11 | 1.342 (4) | C38—H38 | 0.95 |
C4—C10 | 1.416 (5) | C39—C40 | 1.380 (5) |
C5—C6 | 1.349 (5) | C39—H39 | 0.95 |
C5—C10 | 1.403 (5) | C40—H40 | 0.95 |
C5—H5 | 0.95 | C41—C42 | 1.162 (6) |
C6—O20 | 1.338 (4) | C42—H42 | 0.95 |
C6—C7 | 1.423 (4) | O43—C44 | 1.430 (4) |
C7—O22 | 1.339 (4) | C44—H44A | 0.98 |
C7—C8 | 1.350 (5) | C44—H44B | 0.98 |
C8—C9 | 1.386 (5) | C44—H44C | 0.98 |
C8—H8 | 0.95 | O45—C46 | 1.428 (4) |
C9—C10 | 1.397 (4) | C46—H46A | 0.98 |
N11—C12 | 1.400 (4) | C46—H46B | 0.98 |
N11—H11 | 0.92 (4) | C46—H46C | 0.98 |
C12—C17 | 1.359 (5) | O47—C49 | 1.231 (4) |
C12—C13 | 1.390 (4) | O48—C49 | 1.257 (4) |
C13—C14 | 1.381 (5) | C49—C50 | 1.510 (4) |
C13—H13 | 0.95 | C50—C51 | 1.527 (5) |
C14—C15 | 1.381 (5) | C50—H50A | 0.99 |
C14—C18 | 1.427 (5) | C50—H50B | 0.99 |
C15—C16 | 1.366 (5) | C51—C52 | 1.513 (4) |
C15—H15 | 0.95 | C51—H51A | 0.99 |
C16—C17 | 1.366 (5) | C51—H51B | 0.99 |
C16—H16 | 0.95 | C52—C53 | 1.503 (5) |
C17—H17 | 0.95 | C52—H52A | 0.99 |
C18—C19 | 1.174 (5) | C52—H52B | 0.99 |
C19—H19 | 0.95 | C53—C54 | 1.511 (4) |
O20—C21 | 1.431 (4) | C53—H53A | 0.99 |
C21—H21A | 0.98 | C53—H53B | 0.99 |
C21—H21B | 0.98 | C54—O56 | 1.231 (4) |
C21—H21C | 0.98 | C54—O55 | 1.265 (4) |
O22—C23 | 1.439 (4) | O57—C59 | 1.288 (4) |
C23—H23A | 0.98 | O57—H57 | 0.87 (3) |
C23—H23B | 0.98 | O58—C59 | 1.211 (4) |
C23—H23C | 0.98 | C59—C60 | 1.483 (5) |
N24—C25 | 1.312 (4) | C60—C61 | 1.517 (5) |
N24—C32 | 1.362 (4) | C60—H60A | 0.99 |
N24—H24 | 0.97 (3) | C60—H60B | 0.99 |
C25—N26 | 1.320 (4) | C61—C61i | 1.508 (6) |
C25—H25 | 0.95 | C61—H61A | 0.99 |
N26—C27 | 1.325 (4) | C61—H61B | 0.99 |
C27—N34 | 1.342 (4) | O62—C64 | 1.302 (4) |
C27—C33 | 1.417 (5) | O62—H62 | 0.90 (3) |
C28—C29 | 1.348 (5) | O63—C64 | 1.195 (4) |
C28—C33 | 1.391 (5) | C64—C65 | 1.470 (5) |
C28—H28 | 0.95 | C65—C66 | 1.500 (5) |
C29—O43 | 1.341 (4) | C65—H65A | 0.99 |
C29—C30 | 1.421 (4) | C65—H65B | 0.99 |
C30—O45 | 1.334 (4) | C66—C66ii | 1.500 (7) |
C30—C31 | 1.346 (5) | C66—H66A | 0.99 |
C31—C32 | 1.382 (5) | C66—H66B | 0.99 |
C31—H31 | 0.95 | C67—O68 | 1.413 (5) |
C32—C33 | 1.397 (4) | C67—H67A | 0.98 |
N34—C35 | 1.419 (4) | C67—H67B | 0.98 |
N34—H34 | 0.88 (4) | C67—H67C | 0.98 |
C35—C40 | 1.367 (5) | O68—H68 | 0.88 (3) |
| | | |
C2—N1—C9 | 119.5 (3) | C35—C36—H36 | 120.6 |
C2—N1—H1 | 118 (2) | C37—C36—H36 | 120.6 |
C9—N1—H1 | 122 (3) | C38—C37—C36 | 119.8 (3) |
N1—C2—N3 | 125.7 (3) | C38—C37—C41 | 120.7 (4) |
N1—C2—H2 | 117.2 | C36—C37—C41 | 119.5 (4) |
N3—C2—H2 | 117.2 | C39—C38—C37 | 120.7 (4) |
C2—N3—C4 | 117.8 (3) | C39—C38—H38 | 119.7 |
N3—C4—N11 | 118.9 (3) | C37—C38—H38 | 119.7 |
N3—C4—C10 | 121.0 (3) | C38—C39—C40 | 119.9 (4) |
N11—C4—C10 | 120.1 (3) | C38—C39—H39 | 120.1 |
C6—C5—C10 | 120.1 (3) | C40—C39—H39 | 120.1 |
C6—C5—H5 | 120.0 | C35—C40—C39 | 119.8 (3) |
C10—C5—H5 | 120.0 | C35—C40—H40 | 120.1 |
O20—C6—C5 | 124.5 (3) | C39—C40—H40 | 120.1 |
O20—C6—C7 | 115.0 (3) | C42—C41—C37 | 177.7 (5) |
C5—C6—C7 | 120.5 (3) | C41—C42—H42 | 180.0 |
O22—C7—C8 | 123.9 (3) | C29—O43—C44 | 116.9 (3) |
O22—C7—C6 | 115.3 (3) | O43—C44—H44A | 109.5 |
C8—C7—C6 | 120.8 (3) | O43—C44—H44B | 109.5 |
C7—C8—C9 | 118.3 (3) | H44A—C44—H44B | 109.5 |
C7—C8—H8 | 120.9 | O43—C44—H44C | 109.5 |
C9—C8—H8 | 120.9 | H44A—C44—H44C | 109.5 |
N1—C9—C8 | 119.0 (3) | H44B—C44—H44C | 109.5 |
N1—C9—C10 | 118.7 (3) | C30—O45—C46 | 116.3 (3) |
C8—C9—C10 | 122.3 (3) | O45—C46—H46A | 109.5 |
C9—C10—C5 | 118.0 (3) | O45—C46—H46B | 109.5 |
C9—C10—C4 | 117.3 (3) | H46A—C46—H46B | 109.5 |
C5—C10—C4 | 124.7 (3) | O45—C46—H46C | 109.5 |
C4—N11—C12 | 130.4 (3) | H46A—C46—H46C | 109.5 |
C4—N11—H11 | 118 (2) | H46B—C46—H46C | 109.5 |
C12—N11—H11 | 112 (2) | O47—C49—O48 | 122.6 (3) |
C17—C12—C13 | 119.1 (3) | O47—C49—C50 | 120.0 (3) |
C17—C12—N11 | 125.7 (3) | O48—C49—C50 | 117.4 (3) |
C13—C12—N11 | 115.2 (3) | C49—C50—C51 | 111.2 (3) |
C14—C13—C12 | 121.3 (3) | C49—C50—H50A | 109.4 |
C14—C13—H13 | 119.4 | C51—C50—H50A | 109.4 |
C12—C13—H13 | 119.4 | C49—C50—H50B | 109.4 |
C13—C14—C15 | 118.7 (3) | C51—C50—H50B | 109.4 |
C13—C14—C18 | 119.2 (4) | H50A—C50—H50B | 108.0 |
C15—C14—C18 | 122.1 (3) | C52—C51—C50 | 112.5 (3) |
C16—C15—C14 | 119.2 (4) | C52—C51—H51A | 109.1 |
C16—C15—H15 | 120.4 | C50—C51—H51A | 109.1 |
C14—C15—H15 | 120.4 | C52—C51—H51B | 109.1 |
C15—C16—C17 | 122.2 (4) | C50—C51—H51B | 109.1 |
C15—C16—H16 | 118.9 | H51A—C51—H51B | 107.8 |
C17—C16—H16 | 118.9 | C53—C52—C51 | 113.0 (3) |
C12—C17—C16 | 119.6 (4) | C53—C52—H52A | 109.0 |
C12—C17—H17 | 120.2 | C51—C52—H52A | 109.0 |
C16—C17—H17 | 120.2 | C53—C52—H52B | 109.0 |
C19—C18—C14 | 175.4 (5) | C51—C52—H52B | 109.0 |
C18—C19—H19 | 180.0 | H52A—C52—H52B | 107.8 |
C6—O20—C21 | 117.0 (3) | C52—C53—C54 | 115.5 (3) |
O20—C21—H21A | 109.5 | C52—C53—H53A | 108.4 |
O20—C21—H21B | 109.5 | C54—C53—H53A | 108.4 |
H21A—C21—H21B | 109.5 | C52—C53—H53B | 108.4 |
O20—C21—H21C | 109.5 | C54—C53—H53B | 108.4 |
H21A—C21—H21C | 109.5 | H53A—C53—H53B | 107.5 |
H21B—C21—H21C | 109.5 | O56—C54—O55 | 125.2 (3) |
C7—O22—C23 | 117.0 (3) | O56—C54—C53 | 119.4 (3) |
O22—C23—H23A | 109.5 | O55—C54—C53 | 115.4 (3) |
O22—C23—H23B | 109.5 | C59—O57—H57 | 112 (3) |
H23A—C23—H23B | 109.5 | O58—C59—O57 | 122.2 (3) |
O22—C23—H23C | 109.5 | O58—C59—C60 | 123.9 (3) |
H23A—C23—H23C | 109.5 | O57—C59—C60 | 113.8 (3) |
H23B—C23—H23C | 109.5 | C59—C60—C61 | 112.2 (3) |
C25—N24—C32 | 119.3 (3) | C59—C60—H60A | 109.2 |
C25—N24—H24 | 124 (3) | C61—C60—H60A | 109.2 |
C32—N24—H24 | 116 (3) | C59—C60—H60B | 109.2 |
N24—C25—N26 | 125.6 (3) | C61—C60—H60B | 109.2 |
N24—C25—H25 | 117.2 | H60A—C60—H60B | 107.9 |
N26—C25—H25 | 117.2 | C61i—C61—C60 | 111.9 (4) |
C25—N26—C27 | 117.4 (3) | C61i—C61—H61A | 109.2 |
N26—C27—N34 | 116.7 (3) | C60—C61—H61A | 109.2 |
N26—C27—C33 | 122.0 (3) | C61i—C61—H61B | 109.2 |
N34—C27—C33 | 121.3 (3) | C60—C61—H61B | 109.2 |
C29—C28—C33 | 120.4 (3) | H61A—C61—H61B | 107.9 |
C29—C28—H28 | 119.8 | C64—O62—H62 | 110 (3) |
C33—C28—H28 | 119.8 | O63—C64—O62 | 122.5 (4) |
O43—C29—C28 | 125.0 (3) | O63—C64—C65 | 123.6 (4) |
O43—C29—C30 | 114.5 (3) | O62—C64—C65 | 113.8 (3) |
C28—C29—C30 | 120.4 (3) | C64—C65—C66 | 112.6 (3) |
O45—C30—C31 | 124.4 (3) | C64—C65—H65A | 109.1 |
O45—C30—C29 | 115.5 (3) | C66—C65—H65A | 109.1 |
C31—C30—C29 | 120.0 (3) | C64—C65—H65B | 109.1 |
C30—C31—C32 | 119.2 (3) | C66—C65—H65B | 109.1 |
C30—C31—H31 | 120.4 | H65A—C65—H65B | 107.8 |
C32—C31—H31 | 120.4 | C65—C66—C66ii | 112.5 (4) |
N24—C32—C31 | 119.3 (3) | C65—C66—H66A | 109.1 |
N24—C32—C33 | 119.1 (3) | C66ii—C66—H66A | 109.1 |
C31—C32—C33 | 121.6 (3) | C65—C66—H66B | 109.1 |
C28—C33—C32 | 118.2 (3) | C66ii—C66—H66B | 109.1 |
C28—C33—C27 | 125.3 (3) | H66A—C66—H66B | 107.8 |
C32—C33—C27 | 116.6 (3) | O68—C67—H67A | 109.5 |
C27—N34—C35 | 123.2 (3) | O68—C67—H67B | 109.5 |
C27—N34—H34 | 118 (2) | H67A—C67—H67B | 109.5 |
C35—N34—H34 | 119 (2) | O68—C67—H67C | 109.5 |
C40—C35—C36 | 121.0 (3) | H67A—C67—H67C | 109.5 |
C40—C35—N34 | 119.6 (3) | H67B—C67—H67C | 109.5 |
C36—C35—N34 | 119.3 (3) | C67—O68—H68 | 107 (6) |
C35—C36—C37 | 118.7 (3) | | |
| | | |
C9—N1—C2—N3 | −1.6 (5) | C28—C29—C30—O45 | 175.9 (3) |
N1—C2—N3—C4 | 1.6 (5) | O43—C29—C30—C31 | 176.6 (3) |
C2—N3—C4—N11 | 179.9 (3) | C28—C29—C30—C31 | −4.1 (5) |
C2—N3—C4—C10 | −0.1 (5) | O45—C30—C31—C32 | −177.3 (3) |
C10—C5—C6—O20 | 178.6 (3) | C29—C30—C31—C32 | 2.7 (5) |
C10—C5—C6—C7 | −0.8 (5) | C25—N24—C32—C31 | −179.1 (3) |
O20—C6—C7—O22 | 1.3 (4) | C25—N24—C32—C33 | 1.7 (5) |
C5—C6—C7—O22 | −179.3 (3) | C30—C31—C32—N24 | −178.1 (3) |
O20—C6—C7—C8 | −178.8 (3) | C30—C31—C32—C33 | 1.1 (5) |
C5—C6—C7—C8 | 0.6 (5) | C29—C28—C33—C32 | 2.2 (5) |
O22—C7—C8—C9 | −179.7 (3) | C29—C28—C33—C27 | −178.6 (3) |
C6—C7—C8—C9 | 0.4 (5) | N24—C32—C33—C28 | 175.6 (3) |
C2—N1—C9—C8 | 179.3 (3) | C31—C32—C33—C28 | −3.6 (5) |
C2—N1—C9—C10 | 0.0 (5) | N24—C32—C33—C27 | −3.6 (5) |
C7—C8—C9—N1 | 179.4 (3) | C31—C32—C33—C27 | 177.2 (3) |
C7—C8—C9—C10 | −1.3 (5) | N26—C27—C33—C28 | −176.1 (3) |
N1—C9—C10—C5 | −179.6 (3) | N34—C27—C33—C28 | 2.1 (5) |
C8—C9—C10—C5 | 1.1 (5) | N26—C27—C33—C32 | 3.1 (5) |
N1—C9—C10—C4 | 1.3 (5) | N34—C27—C33—C32 | −178.8 (3) |
C8—C9—C10—C4 | −178.0 (3) | N26—C27—N34—C35 | −2.6 (5) |
C6—C5—C10—C9 | 0.0 (5) | C33—C27—N34—C35 | 179.2 (3) |
C6—C5—C10—C4 | 178.9 (3) | C27—N34—C35—C40 | 116.9 (4) |
N3—C4—C10—C9 | −1.3 (5) | C27—N34—C35—C36 | −64.9 (5) |
N11—C4—C10—C9 | 178.7 (3) | C40—C35—C36—C37 | −0.9 (5) |
N3—C4—C10—C5 | 179.7 (3) | N34—C35—C36—C37 | −179.1 (3) |
N11—C4—C10—C5 | −0.2 (5) | C35—C36—C37—C38 | −0.4 (5) |
N3—C4—N11—C12 | 3.0 (5) | C35—C36—C37—C41 | 177.9 (3) |
C10—C4—N11—C12 | −177.1 (3) | C36—C37—C38—C39 | 1.1 (5) |
C4—N11—C12—C17 | −8.5 (6) | C41—C37—C38—C39 | −177.2 (3) |
C4—N11—C12—C13 | 171.2 (3) | C37—C38—C39—C40 | −0.5 (5) |
C17—C12—C13—C14 | −0.5 (5) | C36—C35—C40—C39 | 1.5 (5) |
N11—C12—C13—C14 | 179.7 (3) | N34—C35—C40—C39 | 179.7 (3) |
C12—C13—C14—C15 | −0.4 (5) | C38—C39—C40—C35 | −0.8 (5) |
C12—C13—C14—C18 | 177.2 (3) | C28—C29—O43—C44 | 1.4 (5) |
C13—C14—C15—C16 | 0.8 (6) | C30—C29—O43—C44 | −179.2 (3) |
C18—C14—C15—C16 | −176.7 (4) | C31—C30—O45—C46 | −1.9 (5) |
C14—C15—C16—C17 | −0.3 (6) | C29—C30—O45—C46 | 178.2 (3) |
C13—C12—C17—C16 | 1.1 (6) | O47—C49—C50—C51 | −97.3 (4) |
N11—C12—C17—C16 | −179.2 (3) | O48—C49—C50—C51 | 80.6 (4) |
C15—C16—C17—C12 | −0.7 (6) | C49—C50—C51—C52 | −178.3 (3) |
C5—C6—O20—C21 | −8.2 (5) | C50—C51—C52—C53 | −179.3 (3) |
C7—C6—O20—C21 | 171.2 (3) | C51—C52—C53—C54 | 179.5 (3) |
C8—C7—O22—C23 | 5.4 (5) | C52—C53—C54—O56 | −0.1 (5) |
C6—C7—O22—C23 | −174.7 (3) | C52—C53—C54—O55 | 179.6 (3) |
C32—N24—C25—N26 | 1.2 (5) | O58—C59—C60—C61 | 101.4 (4) |
N24—C25—N26—C27 | −1.8 (5) | O57—C59—C60—C61 | −77.9 (4) |
C25—N26—C27—N34 | −178.7 (3) | C59—C60—C61—C61i | −177.2 (4) |
C25—N26—C27—C33 | −0.5 (5) | O63—C64—C65—C66 | 32.3 (5) |
C33—C28—C29—O43 | −179.2 (3) | O62—C64—C65—C66 | −150.3 (3) |
C33—C28—C29—C30 | 1.5 (5) | C64—C65—C66—C66ii | −177.0 (4) |
O43—C29—C30—O45 | −3.5 (4) | | |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O48 | 0.97 (3) | 1.75 (3) | 2.717 (4) | 175 (4) |
N11—H11···O56iii | 0.92 (4) | 2.01 (4) | 2.908 (4) | 164 (3) |
N24—H24···O55iii | 0.97 (3) | 1.63 (3) | 2.599 (4) | 175 (4) |
N34—H34···O58i | 0.88 (4) | 2.02 (4) | 2.863 (4) | 159 (3) |
O57—H57···O47iv | 0.87 (3) | 1.67 (3) | 2.536 (4) | 171 (5) |
O62—H62···O48i | 0.90 (3) | 1.70 (3) | 2.592 (4) | 170 (5) |
O68—H68···O56 | 0.88 (3) | 1.98 (5) | 2.770 (4) | 148 (8) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (iii) x, y, z+1; (iv) −x+2, −y+1, −z+1. |
Crystal data top
C18H15N3O2·0.5(C4H6O4) | F(000) = 764 |
Mr = 364.37 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.145 (4) Å | Cell parameters from 3472 reflections |
b = 18.472 (7) Å | θ = 3.0–25.2° |
c = 9.421 (3) Å | µ = 0.10 mm−1 |
β = 91.423 (19)° | T = 130 K |
V = 1764.9 (11) Å3 | Blocks, colourless |
Z = 4 | 0.27 × 0.24 × 0.16 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3419 independent reflections |
Radiation source: Fine-focus sealed tube | 2215 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
φ and ω scans | θmax = 26.1°, θmin = 2.0° |
Absorption correction: multi-scan SADABS | h = −12→12 |
Tmin = 0.97, Tmax = 0.98 | k = −22→22 |
28660 measured reflections | l = −11→11 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.2707P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3419 reflections | Δρmax = 0.26 e Å−3 |
255 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Extinction correction: SHELXL-2014/7 (Sheldrick 2014) |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0050 (11) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.51651 (18) | 0.53982 (9) | 0.77636 (18) | 0.0273 (4) | |
C2 | 0.4391 (2) | 0.48388 (12) | 0.7941 (2) | 0.0288 (5) | |
H2 | 0.4561 | 0.4557 | 0.8769 | 0.035* | |
N3 | 0.33813 (18) | 0.46140 (9) | 0.70914 (18) | 0.0281 (4) | |
C4 | 0.3150 (2) | 0.49941 (11) | 0.5901 (2) | 0.0243 (5) | |
C5 | 0.3707 (2) | 0.60615 (11) | 0.4354 (2) | 0.0247 (5) | |
H5 | 0.3042 | 0.5936 | 0.3671 | 0.03* | |
C6 | 0.4460 (2) | 0.66645 (11) | 0.4161 (2) | 0.0254 (5) | |
C7 | 0.5452 (2) | 0.68637 (11) | 0.5188 (2) | 0.0265 (5) | |
C8 | 0.5674 (2) | 0.64392 (11) | 0.6369 (2) | 0.0272 (5) | |
H8 | 0.6341 | 0.6568 | 0.7049 | 0.033* | |
C9 | 0.4911 (2) | 0.58153 (11) | 0.6565 (2) | 0.0253 (5) | |
C10 | 0.3916 (2) | 0.56205 (11) | 0.5574 (2) | 0.0237 (5) | |
H11 | 0.207 (2) | 0.5055 (12) | 0.419 (2) | 0.031 (6)* | |
N11 | 0.21595 (18) | 0.47807 (9) | 0.49875 (19) | 0.0256 (4) | |
C12 | 0.1267 (2) | 0.41941 (11) | 0.5067 (2) | 0.0266 (5) | |
C13 | 0.0353 (2) | 0.41364 (11) | 0.3935 (2) | 0.0272 (5) | |
H13 | 0.0356 | 0.4487 | 0.3198 | 0.033* | |
C14 | −0.0561 (2) | 0.35748 (11) | 0.3869 (2) | 0.0283 (5) | |
C15 | −0.0570 (2) | 0.30668 (12) | 0.4970 (2) | 0.0350 (6) | |
H15 | −0.1182 | 0.2678 | 0.4944 | 0.042* | |
C16 | 0.0322 (2) | 0.31368 (13) | 0.6094 (3) | 0.0389 (6) | |
H16 | 0.0306 | 0.2792 | 0.6842 | 0.047* | |
C17 | 0.1244 (2) | 0.36943 (12) | 0.6170 (2) | 0.0336 (6) | |
H17 | 0.1843 | 0.3733 | 0.6957 | 0.04* | |
C18 | −0.1490 (2) | 0.35361 (12) | 0.2677 (2) | 0.0310 (5) | |
C19 | −0.2273 (3) | 0.35234 (13) | 0.1714 (3) | 0.0403 (6) | |
H19 | −0.2897 | 0.3513 | 0.0945 | 0.048* | |
O20 | 0.43352 (15) | 0.71195 (8) | 0.30247 (15) | 0.0321 (4) | |
C21 | 0.3405 (2) | 0.69172 (12) | 0.1930 (2) | 0.0347 (6) | |
H21A | 0.3645 | 0.6443 | 0.1548 | 0.052* | |
H21B | 0.3413 | 0.7278 | 0.1168 | 0.052* | |
H21C | 0.2521 | 0.6891 | 0.2323 | 0.052* | |
O22 | 0.61062 (15) | 0.74870 (8) | 0.48992 (15) | 0.0343 (4) | |
C23 | 0.7077 (2) | 0.77249 (13) | 0.5941 (2) | 0.0382 (6) | |
H23A | 0.666 | 0.7782 | 0.6862 | 0.057* | |
H23B | 0.7447 | 0.8189 | 0.5645 | 0.057* | |
H23C | 0.7783 | 0.7364 | 0.6025 | 0.057* | |
O24 | 0.82302 (15) | 0.46782 (8) | 0.81886 (16) | 0.0362 (4) | |
H25 | 0.654 (3) | 0.5508 (16) | 0.870 (3) | 0.077 (10)* | |
O25 | 0.72992 (16) | 0.55982 (9) | 0.93348 (17) | 0.0362 (4) | |
C26 | 0.8266 (2) | 0.51419 (11) | 0.9120 (2) | 0.0270 (5) | |
C27 | 0.9433 (2) | 0.52588 (12) | 1.0112 (2) | 0.0320 (5) | |
H27A | 0.9139 | 0.5209 | 1.1102 | 0.038* | |
H27B | 0.9756 | 0.576 | 0.9993 | 0.038* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0247 (10) | 0.0293 (10) | 0.0277 (10) | 0.0030 (8) | −0.0027 (8) | −0.0014 (8) |
C2 | 0.0260 (12) | 0.0308 (13) | 0.0295 (12) | 0.0025 (10) | −0.0029 (10) | 0.0051 (9) |
N3 | 0.0265 (10) | 0.0271 (10) | 0.0305 (10) | 0.0020 (8) | −0.0025 (9) | 0.0020 (8) |
C4 | 0.0215 (11) | 0.0251 (12) | 0.0263 (11) | 0.0048 (9) | −0.0003 (9) | −0.0031 (9) |
C5 | 0.0222 (11) | 0.0255 (12) | 0.0262 (11) | 0.0025 (9) | −0.0040 (9) | −0.0031 (9) |
C6 | 0.0257 (12) | 0.0236 (11) | 0.0269 (11) | 0.0026 (9) | −0.0015 (10) | −0.0019 (9) |
C7 | 0.0257 (12) | 0.0220 (12) | 0.0318 (12) | −0.0001 (9) | 0.0017 (10) | −0.0037 (9) |
C8 | 0.0234 (12) | 0.0266 (12) | 0.0314 (12) | −0.0008 (9) | −0.0026 (10) | −0.0076 (9) |
C9 | 0.0232 (11) | 0.0264 (12) | 0.0264 (11) | 0.0042 (9) | 0.0011 (10) | −0.0034 (9) |
C10 | 0.0214 (11) | 0.0234 (11) | 0.0263 (11) | 0.0036 (9) | −0.0002 (9) | −0.0018 (9) |
N11 | 0.0273 (10) | 0.0233 (10) | 0.0260 (10) | −0.0020 (8) | −0.0022 (8) | 0.0014 (8) |
C12 | 0.0233 (12) | 0.0240 (12) | 0.0324 (12) | 0.0026 (9) | 0.0013 (10) | −0.0035 (9) |
C13 | 0.0281 (12) | 0.0245 (12) | 0.0291 (12) | 0.0002 (9) | 0.0013 (10) | 0.0000 (9) |
C14 | 0.0251 (12) | 0.0274 (12) | 0.0323 (12) | −0.0003 (10) | 0.0010 (10) | −0.0055 (9) |
C15 | 0.0318 (14) | 0.0300 (13) | 0.0431 (13) | −0.0078 (10) | −0.0011 (12) | 0.0029 (10) |
C16 | 0.0393 (15) | 0.0353 (14) | 0.0418 (14) | −0.0075 (11) | −0.0031 (12) | 0.0119 (11) |
C17 | 0.0316 (13) | 0.0317 (13) | 0.0371 (13) | −0.0044 (10) | −0.0064 (11) | 0.0043 (10) |
C18 | 0.0301 (13) | 0.0260 (12) | 0.0371 (13) | −0.0008 (10) | 0.0037 (12) | −0.0031 (10) |
C19 | 0.0399 (15) | 0.0388 (15) | 0.0419 (14) | 0.0027 (12) | −0.0079 (13) | −0.0093 (11) |
O20 | 0.0331 (9) | 0.0295 (9) | 0.0332 (8) | −0.0062 (7) | −0.0101 (7) | 0.0053 (7) |
C21 | 0.0385 (14) | 0.0348 (14) | 0.0304 (12) | −0.0047 (11) | −0.0098 (11) | 0.0041 (10) |
O22 | 0.0340 (9) | 0.0314 (9) | 0.0371 (9) | −0.0096 (7) | −0.0077 (8) | 0.0017 (7) |
C23 | 0.0364 (14) | 0.0397 (14) | 0.0381 (13) | −0.0120 (11) | −0.0068 (12) | −0.0018 (11) |
O24 | 0.0341 (10) | 0.0346 (9) | 0.0393 (9) | 0.0009 (7) | −0.0082 (8) | −0.0073 (7) |
O25 | 0.0280 (9) | 0.0432 (10) | 0.0369 (9) | 0.0053 (8) | −0.0077 (8) | −0.0073 (7) |
C26 | 0.0281 (12) | 0.0258 (12) | 0.0271 (11) | −0.0013 (10) | −0.0010 (10) | 0.0043 (9) |
C27 | 0.0312 (13) | 0.0343 (13) | 0.0303 (12) | 0.0008 (10) | −0.0044 (11) | −0.0036 (10) |
Geometric parameters (Å, º) top
N1—C2 | 1.311 (3) | C14—C18 | 1.450 (3) |
N1—C9 | 1.386 (3) | C15—C16 | 1.382 (3) |
C2—N3 | 1.349 (3) | C15—H15 | 0.95 |
C2—H2 | 0.95 | C16—C17 | 1.391 (3) |
N3—C4 | 1.339 (3) | C16—H16 | 0.95 |
C4—N11 | 1.365 (3) | C17—H17 | 0.95 |
C4—C10 | 1.432 (3) | C18—C19 | 1.191 (3) |
C5—C6 | 1.365 (3) | C19—H19 | 0.95 |
C5—C10 | 1.421 (3) | O20—C21 | 1.430 (3) |
C5—H5 | 0.95 | C21—H21A | 0.98 |
C6—O20 | 1.364 (2) | C21—H21B | 0.98 |
C6—C7 | 1.427 (3) | C21—H21C | 0.98 |
C7—O22 | 1.360 (2) | O22—C23 | 1.441 (2) |
C7—C8 | 1.376 (3) | C23—H23A | 0.98 |
C8—C9 | 1.403 (3) | C23—H23B | 0.98 |
C8—H8 | 0.95 | C23—H23C | 0.98 |
C9—C10 | 1.404 (3) | O24—C26 | 1.226 (2) |
N11—C12 | 1.415 (3) | O25—C26 | 1.313 (3) |
N11—H11 | 0.91 (2) | O25—H25 | 0.98 (2) |
C12—C17 | 1.391 (3) | C26—C27 | 1.506 (3) |
C12—C13 | 1.400 (3) | C27—C27i | 1.514 (4) |
C13—C14 | 1.391 (3) | C27—H27A | 0.99 |
C13—H13 | 0.95 | C27—H27B | 0.99 |
C14—C15 | 1.399 (3) | | |
| | | |
C2—N1—C9 | 116.22 (18) | C15—C14—C18 | 121.7 (2) |
N1—C2—N3 | 127.97 (19) | C16—C15—C14 | 119.3 (2) |
N1—C2—H2 | 116.0 | C16—C15—H15 | 120.3 |
N3—C2—H2 | 116.0 | C14—C15—H15 | 120.3 |
C4—N3—C2 | 116.75 (18) | C15—C16—C17 | 122.3 (2) |
N3—C4—N11 | 119.20 (19) | C15—C16—H16 | 118.9 |
N3—C4—C10 | 121.26 (19) | C17—C16—H16 | 118.9 |
N11—C4—C10 | 119.55 (18) | C12—C17—C16 | 118.5 (2) |
C6—C5—C10 | 120.2 (2) | C12—C17—H17 | 120.7 |
C6—C5—H5 | 119.9 | C16—C17—H17 | 120.7 |
C10—C5—H5 | 119.9 | C19—C18—C14 | 177.9 (2) |
O20—C6—C5 | 124.47 (19) | C18—C19—H19 | 180.0 |
O20—C6—C7 | 115.05 (18) | C6—O20—C21 | 116.84 (16) |
C5—C6—C7 | 120.48 (19) | O20—C21—H21A | 109.5 |
O22—C7—C8 | 124.98 (19) | O20—C21—H21B | 109.5 |
O22—C7—C6 | 114.97 (18) | H21A—C21—H21B | 109.5 |
C8—C7—C6 | 120.04 (19) | O20—C21—H21C | 109.5 |
C7—C8—C9 | 119.6 (2) | H21A—C21—H21C | 109.5 |
C7—C8—H8 | 120.2 | H21B—C21—H21C | 109.5 |
C9—C8—H8 | 120.2 | C7—O22—C23 | 116.77 (16) |
N1—C9—C8 | 118.13 (19) | O22—C23—H23A | 109.5 |
N1—C9—C10 | 121.01 (19) | O22—C23—H23B | 109.5 |
C8—C9—C10 | 120.87 (19) | H23A—C23—H23B | 109.5 |
C9—C10—C5 | 118.77 (19) | O22—C23—H23C | 109.5 |
C9—C10—C4 | 116.71 (18) | H23A—C23—H23C | 109.5 |
C5—C10—C4 | 124.50 (19) | H23B—C23—H23C | 109.5 |
C4—N11—C12 | 130.53 (18) | C26—O25—H25 | 112.2 (18) |
C4—N11—H11 | 114.6 (14) | O24—C26—O25 | 123.3 (2) |
C12—N11—H11 | 114.9 (14) | O24—C26—C27 | 123.6 (2) |
C17—C12—C13 | 119.7 (2) | O25—C26—C27 | 113.03 (19) |
C17—C12—N11 | 124.8 (2) | C26—C27—C27i | 114.2 (2) |
C13—C12—N11 | 115.52 (19) | C26—C27—H27A | 108.7 |
C14—C13—C12 | 121.3 (2) | C27i—C27—H27A | 108.7 |
C14—C13—H13 | 119.4 | C26—C27—H27B | 108.7 |
C12—C13—H13 | 119.4 | C27i—C27—H27B | 108.7 |
C13—C14—C15 | 118.9 (2) | H27A—C27—H27B | 107.6 |
C13—C14—C18 | 119.4 (2) | | |
| | | |
C9—N1—C2—N3 | 0.7 (3) | N11—C4—C10—C9 | 179.36 (18) |
N1—C2—N3—C4 | 1.7 (3) | N3—C4—C10—C5 | −178.25 (19) |
C2—N3—C4—N11 | 178.54 (18) | N11—C4—C10—C5 | 1.4 (3) |
C2—N3—C4—C10 | −1.8 (3) | N3—C4—N11—C12 | 0.1 (3) |
C10—C5—C6—O20 | 179.86 (18) | C10—C4—N11—C12 | −179.5 (2) |
C10—C5—C6—C7 | −0.8 (3) | C4—N11—C12—C17 | −0.1 (4) |
O20—C6—C7—O22 | 1.4 (3) | C4—N11—C12—C13 | 179.4 (2) |
C5—C6—C7—O22 | −177.96 (18) | C17—C12—C13—C14 | −1.9 (3) |
O20—C6—C7—C8 | −179.25 (18) | N11—C12—C13—C14 | 178.63 (18) |
C5—C6—C7—C8 | 1.3 (3) | C12—C13—C14—C15 | 0.9 (3) |
O22—C7—C8—C9 | 178.49 (19) | C12—C13—C14—C18 | 179.98 (19) |
C6—C7—C8—C9 | −0.7 (3) | C13—C14—C15—C16 | 0.3 (3) |
C2—N1—C9—C8 | 176.97 (19) | C18—C14—C15—C16 | −178.8 (2) |
C2—N1—C9—C10 | −2.9 (3) | C14—C15—C16—C17 | −0.5 (4) |
C7—C8—C9—N1 | 179.71 (18) | C13—C12—C17—C16 | 1.6 (3) |
C7—C8—C9—C10 | −0.4 (3) | N11—C12—C17—C16 | −179.0 (2) |
N1—C9—C10—C5 | −179.17 (18) | C15—C16—C17—C12 | −0.4 (4) |
C8—C9—C10—C5 | 0.9 (3) | C5—C6—O20—C21 | −4.2 (3) |
N1—C9—C10—C4 | 2.7 (3) | C7—C6—O20—C21 | 176.47 (18) |
C8—C9—C10—C4 | −177.15 (18) | C8—C7—O22—C23 | −1.9 (3) |
C6—C5—C10—C9 | −0.3 (3) | C6—C7—O22—C23 | 177.35 (18) |
C6—C5—C10—C4 | 177.59 (19) | O24—C26—C27—C27i | −1.2 (4) |
N3—C4—C10—C9 | −0.3 (3) | O25—C26—C27—C27i | −179.9 (2) |
Symmetry code: (i) −x+2, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O25—H25···N1 | 0.98 (2) | 1.64 (2) | 2.618 (2) | 174 (3) |
N11—H11···O24ii | 0.91 (2) | 2.31 (2) | 3.170 (3) | 158.5 (19) |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Crystal data top
C18H15N3O2·0.5(C8H14O4) | Z = 2 |
Mr = 392.42 | F(000) = 414 |
Triclinic, P1 | Dx = 1.308 Mg m−3 |
a = 7.889 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.157 (4) Å | Cell parameters from 2665 reflections |
c = 14.832 (7) Å | θ = 2.4–24.4° |
α = 86.153 (19)° | µ = 0.09 mm−1 |
β = 83.38 (2)° | T = 130 K |
γ = 69.517 (18)° | Blocks, colourless |
V = 996.6 (8) Å3 | 0.28 × 0.20 × 0.12 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3506 independent reflections |
Radiation source: Fine-focus sealed tube | 2377 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
φ and ω scans | θmax = 25.6°, θmin = 1.4° |
Absorption correction: multi-scan SADABS | h = −9→9 |
Tmin = 0.97, Tmax = 0.99 | k = −11→11 |
15029 measured reflections | l = −17→17 |
Refinement top
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)] = 0.049 | Hydrogen site location: mixed |
wR(F2) = 0.151 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0759P)2] where P = (Fo2 + 2Fc2)/3 |
3506 reflections | (Δ/σ)max < 0.001 |
272 parameters | Δρmax = 0.33 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.5049 (3) | 0.6611 (2) | 0.62907 (12) | 0.0233 (5) | |
C2 | 0.4289 (3) | 0.7651 (3) | 0.56568 (16) | 0.0225 (6) | |
H2 | 0.3233 | 0.8496 | 0.5856 | 0.027* | |
N3 | 0.4840 (2) | 0.7643 (2) | 0.47696 (12) | 0.0215 (5) | |
C4 | 0.6265 (3) | 0.6404 (3) | 0.44643 (15) | 0.0192 (5) | |
C5 | 0.8736 (3) | 0.3863 (3) | 0.48137 (15) | 0.0193 (6) | |
H5 | 0.9162 | 0.3721 | 0.4189 | 0.023* | |
C6 | 0.9591 (3) | 0.2779 (3) | 0.54546 (15) | 0.0213 (6) | |
C7 | 0.9013 (3) | 0.3019 (3) | 0.64031 (15) | 0.0230 (6) | |
C8 | 0.7531 (3) | 0.4288 (3) | 0.66750 (15) | 0.0238 (6) | |
H8 | 0.7138 | 0.444 | 0.7302 | 0.029* | |
C9 | 0.6595 (3) | 0.5364 (3) | 0.60203 (15) | 0.0201 (6) | |
C10 | 0.7220 (3) | 0.5187 (3) | 0.50867 (14) | 0.0174 (5) | |
H11 | 0.752 (3) | 0.532 (3) | 0.3311 (15) | 0.031 (7)* | |
N11 | 0.6772 (3) | 0.6318 (2) | 0.35628 (12) | 0.0187 (5) | |
C12 | 0.6008 (3) | 0.7479 (3) | 0.28883 (14) | 0.0188 (5) | |
C13 | 0.5686 (3) | 0.6988 (3) | 0.20754 (14) | 0.0205 (6) | |
H13 | 0.5911 | 0.5912 | 0.2 | 0.025* | |
C14 | 0.5034 (3) | 0.8064 (3) | 0.13660 (15) | 0.0220 (6) | |
C15 | 0.4714 (3) | 0.9632 (3) | 0.14857 (16) | 0.0275 (6) | |
H15 | 0.4277 | 1.0376 | 0.1013 | 0.033* | |
C16 | 0.5035 (3) | 1.0109 (3) | 0.22978 (16) | 0.0280 (6) | |
H16 | 0.4802 | 1.1185 | 0.2376 | 0.034* | |
C17 | 0.5691 (3) | 0.9048 (3) | 0.30013 (16) | 0.0230 (6) | |
H17 | 0.5918 | 0.9393 | 0.355 | 0.028* | |
C18 | 0.4684 (3) | 0.7559 (3) | 0.05265 (16) | 0.0272 (6) | |
C19 | 0.4407 (3) | 0.7144 (3) | −0.01672 (17) | 0.0345 (7) | |
H19 | 0.4186 | 0.6813 | −0.0722 | 0.041* | |
O20 | 1.1032 (2) | 0.14567 (19) | 0.52593 (10) | 0.0281 (4) | |
C21 | 1.1560 (3) | 0.1125 (3) | 0.43072 (16) | 0.0320 (7) | |
H21A | 1.0515 | 0.109 | 0.4022 | 0.048* | |
H21B | 1.2548 | 0.0116 | 0.4247 | 0.048* | |
H21C | 1.1974 | 0.1945 | 0.4008 | 0.048* | |
O22 | 1.0030 (2) | 0.1916 (2) | 0.69722 (10) | 0.0319 (5) | |
C23 | 0.9730 (4) | 0.2246 (4) | 0.79337 (16) | 0.0411 (8) | |
H23A | 0.982 | 0.3267 | 0.8018 | 0.062* | |
H23B | 1.0651 | 0.144 | 0.8258 | 0.062* | |
H23C | 0.8517 | 0.2251 | 0.8174 | 0.062* | |
H24 | 0.384 (5) | 0.677 (4) | 0.7194 (18) | 0.099 (13)* | |
O24 | 0.3148 (2) | 0.7039 (2) | 0.78516 (11) | 0.0325 (5) | |
O25 | 0.0956 (2) | 0.6337 (2) | 0.73686 (11) | 0.0302 (5) | |
C26 | 0.1490 (3) | 0.7026 (3) | 0.79021 (16) | 0.0248 (6) | |
C27 | 0.0194 (3) | 0.7900 (3) | 0.86841 (16) | 0.0288 (6) | |
H27A | −0.0722 | 0.8842 | 0.8439 | 0.035* | |
H27B | 0.0886 | 0.8247 | 0.9088 | 0.035* | |
C28 | −0.0786 (3) | 0.6909 (3) | 0.92413 (16) | 0.0302 (6) | |
H28A | −0.1681 | 0.7567 | 0.9704 | 0.036* | |
H28B | −0.1464 | 0.6553 | 0.8834 | 0.036* | |
C29 | 0.0493 (3) | 0.5487 (3) | 0.97159 (16) | 0.0291 (6) | |
H29A | 0.1186 | 0.5841 | 1.0116 | 0.035* | |
H29B | 0.1376 | 0.4819 | 0.9252 | 0.035* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0215 (11) | 0.0239 (12) | 0.0255 (11) | −0.0097 (10) | −0.0006 (9) | −0.0004 (10) |
C2 | 0.0202 (13) | 0.0209 (14) | 0.0273 (13) | −0.0088 (11) | 0.0024 (10) | −0.0050 (11) |
N3 | 0.0168 (11) | 0.0228 (12) | 0.0243 (11) | −0.0066 (10) | 0.0005 (8) | −0.0018 (9) |
C4 | 0.0157 (13) | 0.0194 (13) | 0.0249 (13) | −0.0092 (11) | −0.0006 (10) | −0.0018 (11) |
C5 | 0.0155 (12) | 0.0232 (14) | 0.0194 (12) | −0.0076 (11) | −0.0003 (10) | 0.0011 (11) |
C6 | 0.0140 (13) | 0.0199 (14) | 0.0284 (14) | −0.0047 (11) | −0.0010 (10) | 0.0013 (11) |
C7 | 0.0180 (13) | 0.0267 (15) | 0.0257 (13) | −0.0099 (12) | −0.0055 (10) | 0.0078 (12) |
C8 | 0.0210 (14) | 0.0337 (16) | 0.0187 (12) | −0.0136 (13) | −0.0010 (10) | 0.0051 (12) |
C9 | 0.0166 (13) | 0.0197 (14) | 0.0253 (13) | −0.0085 (11) | −0.0002 (10) | −0.0010 (11) |
C10 | 0.0157 (12) | 0.0176 (13) | 0.0203 (12) | −0.0074 (11) | −0.0038 (10) | 0.0026 (10) |
N11 | 0.0201 (11) | 0.0151 (11) | 0.0179 (11) | −0.0024 (10) | −0.0016 (8) | −0.0002 (9) |
C12 | 0.0125 (12) | 0.0208 (14) | 0.0208 (12) | −0.0045 (11) | 0.0011 (9) | 0.0023 (11) |
C13 | 0.0161 (12) | 0.0196 (13) | 0.0251 (13) | −0.0064 (11) | 0.0008 (10) | 0.0010 (11) |
C14 | 0.0158 (12) | 0.0263 (15) | 0.0232 (13) | −0.0075 (11) | −0.0010 (10) | 0.0030 (11) |
C15 | 0.0243 (14) | 0.0256 (15) | 0.0297 (14) | −0.0069 (12) | −0.0018 (11) | 0.0094 (12) |
C16 | 0.0313 (15) | 0.0178 (14) | 0.0331 (15) | −0.0073 (12) | −0.0010 (12) | 0.0011 (12) |
C17 | 0.0236 (14) | 0.0203 (14) | 0.0265 (13) | −0.0098 (12) | −0.0008 (10) | −0.0020 (11) |
C18 | 0.0231 (14) | 0.0324 (16) | 0.0257 (14) | −0.0103 (12) | −0.0027 (11) | 0.0071 (12) |
C19 | 0.0340 (16) | 0.0467 (19) | 0.0272 (15) | −0.0190 (14) | −0.0068 (12) | 0.0029 (13) |
O20 | 0.0224 (10) | 0.0253 (11) | 0.0283 (10) | 0.0012 (8) | −0.0020 (7) | 0.0042 (8) |
C21 | 0.0254 (14) | 0.0259 (16) | 0.0359 (16) | 0.0008 (12) | 0.0006 (11) | 0.0016 (13) |
O22 | 0.0257 (10) | 0.0387 (11) | 0.0260 (10) | −0.0055 (9) | −0.0069 (7) | 0.0120 (8) |
C23 | 0.0288 (16) | 0.064 (2) | 0.0251 (15) | −0.0109 (15) | −0.0070 (12) | 0.0137 (14) |
O24 | 0.0306 (10) | 0.0447 (12) | 0.0240 (10) | −0.0169 (9) | 0.0038 (8) | −0.0042 (9) |
O25 | 0.0267 (10) | 0.0335 (11) | 0.0294 (10) | −0.0076 (9) | −0.0076 (8) | −0.0025 (9) |
C26 | 0.0257 (14) | 0.0240 (14) | 0.0212 (13) | −0.0055 (12) | −0.0017 (11) | 0.0058 (11) |
C27 | 0.0251 (14) | 0.0260 (15) | 0.0291 (14) | −0.0020 (12) | 0.0008 (11) | −0.0013 (12) |
C28 | 0.0277 (14) | 0.0312 (16) | 0.0259 (14) | −0.0053 (13) | 0.0043 (11) | 0.0011 (12) |
C29 | 0.0247 (14) | 0.0327 (16) | 0.0256 (14) | −0.0059 (13) | 0.0007 (11) | 0.0020 (12) |
Geometric parameters (Å, º) top
N1—C2 | 1.327 (3) | C16—C17 | 1.392 (3) |
N1—C9 | 1.387 (3) | C16—H16 | 0.95 |
C2—N3 | 1.337 (3) | C17—H17 | 0.95 |
C2—H2 | 0.95 | C18—C19 | 1.189 (3) |
N3—C4 | 1.347 (3) | C19—H19 | 0.95 |
C4—N11 | 1.350 (3) | O20—C21 | 1.447 (3) |
C4—C10 | 1.448 (3) | C21—H21A | 0.98 |
C5—C6 | 1.377 (3) | C21—H21B | 0.98 |
C5—C10 | 1.416 (3) | C21—H21C | 0.98 |
C5—H5 | 0.95 | O22—C23 | 1.453 (3) |
C6—O20 | 1.360 (3) | C23—H23A | 0.98 |
C6—C7 | 1.435 (3) | C23—H23B | 0.98 |
C7—O22 | 1.361 (3) | C23—H23C | 0.98 |
C7—C8 | 1.372 (3) | O24—C26 | 1.305 (3) |
C8—C9 | 1.410 (3) | O24—H24 | 1.06 (2) |
C8—H8 | 0.95 | O25—C26 | 1.237 (3) |
C9—C10 | 1.416 (3) | C26—C27 | 1.520 (3) |
N11—C12 | 1.429 (3) | C27—C28 | 1.532 (3) |
N11—H11 | 0.97 (3) | C27—H27A | 0.99 |
C12—C17 | 1.388 (3) | C27—H27B | 0.99 |
C12—C13 | 1.394 (3) | C28—C29 | 1.526 (3) |
C13—C14 | 1.405 (3) | C28—H28A | 0.99 |
C13—H13 | 0.95 | C28—H28B | 0.99 |
C14—C15 | 1.387 (3) | C29—C29i | 1.531 (5) |
C14—C18 | 1.445 (3) | C29—H29A | 0.99 |
C15—C16 | 1.387 (3) | C29—H29B | 0.99 |
C15—H15 | 0.95 | | |
| | | |
C2—N1—C9 | 117.6 (2) | C17—C16—H16 | 119.2 |
N1—C2—N3 | 127.3 (2) | C12—C17—C16 | 119.0 (2) |
N1—C2—H2 | 116.3 | C12—C17—H17 | 120.5 |
N3—C2—H2 | 116.3 | C16—C17—H17 | 120.5 |
C2—N3—C4 | 117.3 (2) | C19—C18—C14 | 179.5 (3) |
N3—C4—N11 | 118.4 (2) | C18—C19—H19 | 180.0 |
N3—C4—C10 | 120.8 (2) | C6—O20—C21 | 116.38 (17) |
N11—C4—C10 | 120.8 (2) | O20—C21—H21A | 109.5 |
C6—C5—C10 | 119.9 (2) | O20—C21—H21B | 109.5 |
C6—C5—H5 | 120.0 | H21A—C21—H21B | 109.5 |
C10—C5—H5 | 120.0 | O20—C21—H21C | 109.5 |
O20—C6—C5 | 124.3 (2) | H21A—C21—H21C | 109.5 |
O20—C6—C7 | 115.17 (19) | H21B—C21—H21C | 109.5 |
C5—C6—C7 | 120.5 (2) | C7—O22—C23 | 117.3 (2) |
O22—C7—C8 | 125.0 (2) | O22—C23—H23A | 109.5 |
O22—C7—C6 | 115.0 (2) | O22—C23—H23B | 109.5 |
C8—C7—C6 | 120.0 (2) | H23A—C23—H23B | 109.5 |
C7—C8—C9 | 119.8 (2) | O22—C23—H23C | 109.5 |
C7—C8—H8 | 120.1 | H23A—C23—H23C | 109.5 |
C9—C8—H8 | 120.1 | H23B—C23—H23C | 109.5 |
N1—C9—C8 | 119.9 (2) | C26—O24—H24 | 112.4 (19) |
N1—C9—C10 | 119.6 (2) | O25—C26—O24 | 124.0 (2) |
C8—C9—C10 | 120.5 (2) | O25—C26—C27 | 120.0 (2) |
C9—C10—C5 | 119.1 (2) | O24—C26—C27 | 116.1 (2) |
C9—C10—C4 | 117.2 (2) | C26—C27—C28 | 112.8 (2) |
C5—C10—C4 | 123.8 (2) | C26—C27—H27A | 109.0 |
C4—N11—C12 | 126.0 (2) | C28—C27—H27A | 109.0 |
C4—N11—H11 | 119.3 (14) | C26—C27—H27B | 109.0 |
C12—N11—H11 | 113.3 (14) | C28—C27—H27B | 109.0 |
C17—C12—C13 | 119.9 (2) | H27A—C27—H27B | 107.8 |
C17—C12—N11 | 121.9 (2) | C29—C28—C27 | 113.5 (2) |
C13—C12—N11 | 118.1 (2) | C29—C28—H28A | 108.9 |
C12—C13—C14 | 120.8 (2) | C27—C28—H28A | 108.9 |
C12—C13—H13 | 119.6 | C29—C28—H28B | 108.9 |
C14—C13—H13 | 119.6 | C27—C28—H28B | 108.9 |
C15—C14—C13 | 118.9 (2) | H28A—C28—H28B | 107.7 |
C15—C14—C18 | 120.2 (2) | C28—C29—C29i | 113.4 (3) |
C13—C14—C18 | 120.9 (2) | C28—C29—H29A | 108.9 |
C16—C15—C14 | 119.8 (2) | C29i—C29—H29A | 108.9 |
C16—C15—H15 | 120.1 | C28—C29—H29B | 108.9 |
C14—C15—H15 | 120.1 | C29i—C29—H29B | 108.9 |
C15—C16—C17 | 121.6 (2) | H29A—C29—H29B | 107.7 |
C15—C16—H16 | 119.2 | | |
| | | |
C9—N1—C2—N3 | 0.1 (3) | N3—C4—C10—C5 | −179.4 (2) |
N1—C2—N3—C4 | 4.1 (3) | N11—C4—C10—C5 | 1.2 (3) |
C2—N3—C4—N11 | 175.64 (19) | N3—C4—N11—C12 | 4.3 (3) |
C2—N3—C4—C10 | −3.8 (3) | C10—C4—N11—C12 | −176.24 (19) |
C10—C5—C6—O20 | 178.7 (2) | C4—N11—C12—C17 | 45.9 (3) |
C10—C5—C6—C7 | −3.0 (3) | C4—N11—C12—C13 | −138.1 (2) |
O20—C6—C7—O22 | 2.2 (3) | C17—C12—C13—C14 | −0.3 (3) |
C5—C6—C7—O22 | −176.24 (19) | N11—C12—C13—C14 | −176.40 (19) |
O20—C6—C7—C8 | −177.7 (2) | C12—C13—C14—C15 | 0.1 (3) |
C5—C6—C7—C8 | 3.8 (3) | C12—C13—C14—C18 | −179.4 (2) |
O22—C7—C8—C9 | 179.3 (2) | C13—C14—C15—C16 | −0.2 (3) |
C6—C7—C8—C9 | −0.8 (3) | C18—C14—C15—C16 | 179.3 (2) |
C2—N1—C9—C8 | 175.46 (19) | C14—C15—C16—C17 | 0.6 (4) |
C2—N1—C9—C10 | −4.4 (3) | C13—C12—C17—C16 | 0.6 (3) |
C7—C8—C9—N1 | 177.2 (2) | N11—C12—C17—C16 | 176.6 (2) |
C7—C8—C9—C10 | −3.0 (3) | C15—C16—C17—C12 | −0.8 (4) |
N1—C9—C10—C5 | −176.38 (19) | C5—C6—O20—C21 | −6.0 (3) |
C8—C9—C10—C5 | 3.8 (3) | C7—C6—O20—C21 | 175.57 (18) |
N1—C9—C10—C4 | 4.4 (3) | C8—C7—O22—C23 | −11.4 (3) |
C8—C9—C10—C4 | −175.47 (19) | C6—C7—O22—C23 | 168.65 (19) |
C6—C5—C10—C9 | −0.8 (3) | O25—C26—C27—C28 | 50.7 (3) |
C6—C5—C10—C4 | 178.4 (2) | O24—C26—C27—C28 | −128.2 (2) |
N3—C4—C10—C9 | −0.2 (3) | C26—C27—C28—C29 | 63.3 (3) |
N11—C4—C10—C9 | −179.63 (19) | C27—C28—C29—C29i | 179.1 (3) |
Symmetry code: (i) −x, −y+1, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O24—H24···N1 | 1.06 (2) | 1.54 (3) | 2.583 (3) | 168 (3) |
N11—H11···O25ii | 0.97 (3) | 1.85 (3) | 2.804 (3) | 168 (2) |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
Crystal data top
C18H15N3O2·0.5(C12H22O4) | F(000) = 892 |
Mr = 420.48 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5496 (16) Å | Cell parameters from 4114 reflections |
b = 16.434 (4) Å | θ = 2.4–22.1° |
c = 17.094 (4) Å | µ = 0.09 mm−1 |
β = 93.547 (12)° | T = 130 K |
V = 2116.8 (8) Å3 | Blocks, colourless |
Z = 4 | 0.26 × 0.17 × 0.08 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3787 independent reflections |
Radiation source: Fine-focus sealed tube | 2480 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
φ and ω scans | θmax = 25.2°, θmin = 1.7° |
Absorption correction: multi-scan SADABS | h = −9→8 |
Tmin = 0.98, Tmax = 0.99 | k = −19→19 |
36479 measured reflections | l = −20→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.158 | w = 1/[σ2(Fo2) + (0.0776P)2 + 0.6292P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3787 reflections | Δρmax = 0.36 e Å−3 |
291 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Extinction correction: SHELXL-2014/7 (Sheldrick 2014 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0082 (14) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.6254 (3) | 0.65958 (13) | 0.48852 (13) | 0.0293 (6) | |
C2 | 0.7057 (4) | 0.64947 (17) | 0.55798 (17) | 0.0344 (7) | |
H2 | 0.7081 | 0.6954 | 0.5918 | 0.041* | |
N3 | 0.7847 (3) | 0.58218 (14) | 0.58695 (13) | 0.0323 (6) | |
C4 | 0.7814 (3) | 0.51752 (15) | 0.54094 (15) | 0.0246 (6) | |
C5 | 0.7046 (3) | 0.45603 (16) | 0.40816 (15) | 0.0251 (6) | |
H5 | 0.7578 | 0.4055 | 0.4231 | 0.03* | |
C6 | 0.6300 (3) | 0.46588 (15) | 0.33421 (15) | 0.0272 (6) | |
C7 | 0.5480 (3) | 0.54088 (16) | 0.31148 (15) | 0.0270 (6) | |
C8 | 0.5459 (3) | 0.60287 (16) | 0.36330 (15) | 0.0271 (6) | |
H8 | 0.4905 | 0.6528 | 0.3482 | 0.033* | |
C9 | 0.6248 (3) | 0.59394 (15) | 0.43919 (15) | 0.0231 (6) | |
C10 | 0.7032 (3) | 0.52037 (15) | 0.46265 (15) | 0.0235 (6) | |
H11 | 0.844 (3) | 0.4048 (18) | 0.5368 (17) | 0.039 (9)* | |
N11 | 0.8545 (3) | 0.44731 (14) | 0.56861 (13) | 0.0269 (5) | |
C12 | 0.9348 (3) | 0.42888 (16) | 0.64288 (15) | 0.0267 (6) | |
C13 | 1.0138 (3) | 0.35264 (16) | 0.65014 (15) | 0.0260 (6) | |
H13 | 1.0121 | 0.3174 | 0.606 | 0.031* | |
C14 | 1.0952 (3) | 0.32727 (17) | 0.72108 (16) | 0.0292 (6) | |
C15 | 1.0975 (3) | 0.37897 (18) | 0.78553 (16) | 0.0354 (7) | |
H15 | 1.151 | 0.3621 | 0.8346 | 0.042* | |
C16 | 1.0217 (3) | 0.45443 (18) | 0.77759 (16) | 0.0364 (7) | |
H16 | 1.0254 | 0.49 | 0.8215 | 0.044* | |
C17 | 0.9400 (3) | 0.48033 (18) | 0.70726 (15) | 0.0325 (7) | |
H17 | 0.8879 | 0.5329 | 0.7031 | 0.039* | |
C18 | 1.1834 (3) | 0.25032 (18) | 0.72682 (15) | 0.0319 (7) | |
C19 | 1.2620 (4) | 0.1888 (2) | 0.73251 (17) | 0.0398 (8) | |
H19 | 1.3256 | 0.1389 | 0.7371 | 0.048* | |
O20 | 0.6278 (2) | 0.40878 (11) | 0.27656 (10) | 0.0345 (5) | |
C21 | 0.7238 (4) | 0.33589 (17) | 0.29364 (19) | 0.0433 (8) | |
H21A | 0.8485 | 0.349 | 0.3073 | 0.065* | |
H21B | 0.7158 | 0.3003 | 0.2476 | 0.065* | |
H21C | 0.6733 | 0.3081 | 0.3378 | 0.065* | |
O22 | 0.4801 (2) | 0.54319 (11) | 0.23643 (10) | 0.0340 (5) | |
C23 | 0.4111 (4) | 0.61974 (18) | 0.20932 (17) | 0.0403 (8) | |
H23A | 0.3111 | 0.6353 | 0.24 | 0.06* | |
H23B | 0.3707 | 0.6153 | 0.1539 | 0.06* | |
H23C | 0.5042 | 0.6612 | 0.2154 | 0.06* | |
O24 | 0.2162 (2) | 0.71648 (11) | 0.50407 (12) | 0.0404 (5) | |
H25 | 0.503 (5) | 0.737 (2) | 0.463 (2) | 0.096 (14)* | |
O25 | 0.4281 (3) | 0.78249 (12) | 0.44477 (13) | 0.0455 (6) | |
C26 | 0.2657 (4) | 0.77359 (18) | 0.46550 (17) | 0.0335 (7) | |
C27 | 0.1432 (4) | 0.84005 (17) | 0.43659 (17) | 0.0371 (7) | |
H27A | 0.0938 | 0.8262 | 0.3833 | 0.045* | |
H27B | 0.2116 | 0.8912 | 0.4329 | 0.045* | |
C28 | −0.0082 (4) | 0.85381 (18) | 0.48929 (17) | 0.0385 (7) | |
H28A | −0.0699 | 0.8015 | 0.4968 | 0.046* | |
H28B | 0.0408 | 0.8725 | 0.5413 | 0.046* | |
C29 | −0.1411 (4) | 0.91585 (18) | 0.45635 (16) | 0.0364 (7) | |
H29A | −0.1936 | 0.896 | 0.4054 | 0.044* | |
H29B | −0.0783 | 0.9674 | 0.4467 | 0.044* | |
C30 | −0.2888 (3) | 0.93252 (17) | 0.51023 (16) | 0.0338 (7) | |
H30A | −0.3473 | 0.8806 | 0.5227 | 0.041* | |
H30B | −0.2376 | 0.956 | 0.5599 | 0.041* | |
C31 | −0.4260 (3) | 0.99058 (18) | 0.47367 (16) | 0.0370 (7) | |
H31A | −0.3665 | 1.042 | 0.4604 | 0.044* | |
H31B | −0.4775 | 0.9666 | 0.4242 | 0.044* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0296 (12) | 0.0266 (13) | 0.0314 (13) | 0.0020 (10) | 0.0006 (10) | −0.0025 (10) |
C2 | 0.0389 (16) | 0.0305 (16) | 0.0336 (17) | 0.0017 (13) | −0.0003 (13) | −0.0076 (13) |
N3 | 0.0329 (13) | 0.0304 (14) | 0.0333 (14) | 0.0056 (10) | 0.0001 (10) | −0.0014 (11) |
C4 | 0.0215 (13) | 0.0250 (15) | 0.0273 (15) | 0.0000 (11) | 0.0029 (11) | 0.0038 (12) |
C5 | 0.0214 (13) | 0.0221 (14) | 0.0313 (15) | −0.0006 (11) | −0.0009 (11) | 0.0021 (12) |
C6 | 0.0247 (14) | 0.0243 (15) | 0.0322 (16) | −0.0051 (12) | −0.0001 (12) | −0.0061 (12) |
C7 | 0.0199 (13) | 0.0311 (16) | 0.0294 (15) | −0.0027 (12) | −0.0042 (11) | 0.0036 (13) |
C8 | 0.0212 (14) | 0.0268 (15) | 0.0330 (16) | 0.0012 (11) | −0.0015 (12) | 0.0027 (13) |
C9 | 0.0167 (13) | 0.0236 (14) | 0.0291 (15) | −0.0009 (11) | 0.0018 (11) | 0.0015 (12) |
C10 | 0.0182 (13) | 0.0257 (15) | 0.0268 (14) | −0.0032 (11) | 0.0025 (11) | 0.0010 (12) |
N11 | 0.0259 (12) | 0.0279 (13) | 0.0266 (13) | 0.0016 (10) | −0.0021 (10) | −0.0003 (11) |
C12 | 0.0177 (13) | 0.0346 (16) | 0.0278 (15) | −0.0010 (11) | 0.0015 (11) | 0.0035 (12) |
C13 | 0.0224 (13) | 0.0316 (15) | 0.0241 (14) | −0.0009 (12) | 0.0013 (11) | 0.0027 (12) |
C14 | 0.0210 (13) | 0.0367 (17) | 0.0297 (16) | −0.0009 (12) | 0.0008 (11) | 0.0063 (13) |
C15 | 0.0301 (15) | 0.0492 (19) | 0.0263 (16) | 0.0015 (14) | −0.0015 (12) | 0.0042 (14) |
C16 | 0.0374 (16) | 0.0458 (19) | 0.0258 (15) | 0.0017 (14) | −0.0009 (12) | −0.0041 (14) |
C17 | 0.0310 (15) | 0.0384 (17) | 0.0278 (16) | 0.0033 (13) | −0.0010 (12) | −0.0008 (13) |
C18 | 0.0302 (15) | 0.0394 (18) | 0.0252 (16) | −0.0037 (14) | −0.0057 (12) | 0.0064 (13) |
C19 | 0.0398 (17) | 0.0418 (19) | 0.0362 (18) | 0.0035 (15) | −0.0105 (14) | 0.0043 (15) |
O20 | 0.0416 (11) | 0.0261 (11) | 0.0350 (11) | 0.0004 (9) | −0.0048 (9) | −0.0050 (9) |
C21 | 0.0543 (19) | 0.0274 (17) | 0.0475 (19) | 0.0058 (14) | −0.0027 (15) | −0.0068 (14) |
O22 | 0.0361 (11) | 0.0334 (11) | 0.0309 (11) | 0.0033 (9) | −0.0110 (9) | 0.0009 (9) |
C23 | 0.0428 (17) | 0.0406 (18) | 0.0360 (17) | 0.0052 (14) | −0.0096 (14) | 0.0055 (14) |
O24 | 0.0427 (12) | 0.0308 (12) | 0.0469 (13) | 0.0014 (9) | −0.0034 (10) | 0.0107 (10) |
O25 | 0.0357 (12) | 0.0328 (12) | 0.0690 (16) | 0.0066 (10) | 0.0102 (11) | 0.0077 (11) |
C26 | 0.0357 (17) | 0.0311 (17) | 0.0337 (17) | 0.0025 (13) | 0.0009 (13) | −0.0061 (14) |
C27 | 0.0379 (16) | 0.0352 (17) | 0.0380 (17) | 0.0053 (13) | 0.0009 (13) | 0.0015 (14) |
C28 | 0.0392 (16) | 0.0366 (17) | 0.0398 (18) | 0.0059 (14) | 0.0019 (14) | 0.0017 (14) |
C29 | 0.0371 (16) | 0.0376 (17) | 0.0340 (17) | 0.0051 (13) | −0.0026 (13) | 0.0000 (13) |
C30 | 0.0307 (15) | 0.0328 (16) | 0.0374 (17) | 0.0053 (13) | −0.0025 (13) | 0.0003 (13) |
C31 | 0.0365 (16) | 0.0453 (18) | 0.0288 (16) | 0.0056 (14) | −0.0020 (12) | 0.0014 (14) |
Geometric parameters (Å, º) top
N1—C2 | 1.310 (3) | C18—C19 | 1.174 (4) |
N1—C9 | 1.369 (3) | C19—H19 | 0.95 |
C2—N3 | 1.337 (3) | O20—C21 | 1.421 (3) |
C2—H2 | 0.95 | C21—H21A | 0.98 |
N3—C4 | 1.321 (3) | C21—H21B | 0.98 |
C4—N11 | 1.352 (3) | C21—H21C | 0.98 |
C4—C10 | 1.430 (3) | O22—C23 | 1.428 (3) |
C5—C6 | 1.361 (3) | C23—H23A | 0.98 |
C5—C10 | 1.410 (3) | C23—H23B | 0.98 |
C5—H5 | 0.95 | C23—H23C | 0.98 |
C6—O20 | 1.360 (3) | O24—C26 | 1.219 (3) |
C6—C7 | 1.422 (4) | O25—C26 | 1.305 (3) |
C7—C8 | 1.351 (4) | O25—H25 | 0.98 (3) |
C7—O22 | 1.352 (3) | C26—C27 | 1.495 (4) |
C8—C9 | 1.402 (3) | C27—C28 | 1.515 (4) |
C8—H8 | 0.95 | C27—H27A | 0.99 |
C9—C10 | 1.394 (3) | C27—H27B | 0.99 |
N11—C12 | 1.406 (3) | C28—C29 | 1.515 (4) |
N11—H11 | 0.89 (3) | C28—H28A | 0.99 |
C12—C17 | 1.386 (4) | C28—H28B | 0.99 |
C12—C13 | 1.390 (4) | C29—C30 | 1.515 (4) |
C13—C14 | 1.389 (3) | C29—H29A | 0.99 |
C13—H13 | 0.95 | C29—H29B | 0.99 |
C14—C15 | 1.390 (4) | C30—C31 | 1.514 (4) |
C14—C18 | 1.430 (4) | C30—H30A | 0.99 |
C15—C16 | 1.369 (4) | C30—H30B | 0.99 |
C15—H15 | 0.95 | C31—C31i | 1.510 (5) |
C16—C17 | 1.384 (4) | C31—H31A | 0.99 |
C16—H16 | 0.95 | C31—H31B | 0.99 |
C17—H17 | 0.95 | | |
| | | |
C2—N1—C9 | 116.2 (2) | C6—O20—C21 | 116.7 (2) |
N1—C2—N3 | 127.7 (3) | O20—C21—H21A | 109.5 |
N1—C2—H2 | 116.2 | O20—C21—H21B | 109.5 |
N3—C2—H2 | 116.2 | H21A—C21—H21B | 109.5 |
C4—N3—C2 | 116.9 (2) | O20—C21—H21C | 109.5 |
N3—C4—N11 | 119.1 (2) | H21A—C21—H21C | 109.5 |
N3—C4—C10 | 121.5 (2) | H21B—C21—H21C | 109.5 |
N11—C4—C10 | 119.4 (2) | C7—O22—C23 | 116.2 (2) |
C6—C5—C10 | 120.3 (2) | O22—C23—H23A | 109.5 |
C6—C5—H5 | 119.8 | O22—C23—H23B | 109.5 |
C10—C5—H5 | 119.8 | H23A—C23—H23B | 109.5 |
O20—C6—C5 | 125.2 (2) | O22—C23—H23C | 109.5 |
O20—C6—C7 | 114.5 (2) | H23A—C23—H23C | 109.5 |
C5—C6—C7 | 120.3 (2) | H23B—C23—H23C | 109.5 |
C8—C7—O22 | 125.6 (2) | C26—O25—H25 | 111 (2) |
C8—C7—C6 | 119.8 (2) | O24—C26—O25 | 123.9 (3) |
O22—C7—C6 | 114.6 (2) | O24—C26—C27 | 122.5 (3) |
C7—C8—C9 | 120.4 (2) | O25—C26—C27 | 113.6 (3) |
C7—C8—H8 | 119.8 | C26—C27—C28 | 112.7 (2) |
C9—C8—H8 | 119.8 | C26—C27—H27A | 109.0 |
N1—C9—C10 | 121.4 (2) | C28—C27—H27A | 109.0 |
N1—C9—C8 | 118.2 (2) | C26—C27—H27B | 109.0 |
C10—C9—C8 | 120.4 (2) | C28—C27—H27B | 109.0 |
C9—C10—C5 | 118.7 (2) | H27A—C27—H27B | 107.8 |
C9—C10—C4 | 116.2 (2) | C29—C28—C27 | 112.7 (2) |
C5—C10—C4 | 125.1 (2) | C29—C28—H28A | 109.0 |
C4—N11—C12 | 130.1 (2) | C27—C28—H28A | 109.0 |
C4—N11—H11 | 116.2 (18) | C29—C28—H28B | 109.0 |
C12—N11—H11 | 113.6 (18) | C27—C28—H28B | 109.0 |
C17—C12—C13 | 119.2 (2) | H28A—C28—H28B | 107.8 |
C17—C12—N11 | 125.1 (2) | C28—C29—C30 | 113.1 (2) |
C13—C12—N11 | 115.7 (2) | C28—C29—H29A | 109.0 |
C14—C13—C12 | 120.8 (3) | C30—C29—H29A | 109.0 |
C14—C13—H13 | 119.6 | C28—C29—H29B | 109.0 |
C12—C13—H13 | 119.6 | C30—C29—H29B | 109.0 |
C13—C14—C15 | 119.4 (3) | H29A—C29—H29B | 107.8 |
C13—C14—C18 | 120.3 (2) | C31—C30—C29 | 111.9 (2) |
C15—C14—C18 | 120.2 (2) | C31—C30—H30A | 109.2 |
C16—C15—C14 | 119.4 (3) | C29—C30—H30A | 109.2 |
C16—C15—H15 | 120.3 | C31—C30—H30B | 109.2 |
C14—C15—H15 | 120.3 | C29—C30—H30B | 109.2 |
C15—C16—C17 | 121.7 (3) | H30A—C30—H30B | 107.9 |
C15—C16—H16 | 119.1 | C31i—C31—C30 | 113.3 (3) |
C17—C16—H16 | 119.1 | C31i—C31—H31A | 108.9 |
C16—C17—C12 | 119.4 (3) | C30—C31—H31A | 108.9 |
C16—C17—H17 | 120.3 | C31i—C31—H31B | 108.9 |
C12—C17—H17 | 120.3 | C30—C31—H31B | 108.9 |
C19—C18—C14 | 177.3 (3) | H31A—C31—H31B | 107.7 |
C18—C19—H19 | 180.0 | | |
| | | |
C9—N1—C2—N3 | −1.2 (4) | N11—C4—C10—C5 | −4.1 (4) |
N1—C2—N3—C4 | −0.5 (4) | N3—C4—N11—C12 | 1.8 (4) |
C2—N3—C4—N11 | −177.9 (2) | C10—C4—N11—C12 | −178.5 (2) |
C2—N3—C4—C10 | 2.5 (4) | C4—N11—C12—C17 | 6.4 (4) |
C10—C5—C6—O20 | 178.3 (2) | C4—N11—C12—C13 | −173.6 (2) |
C10—C5—C6—C7 | −0.8 (4) | C17—C12—C13—C14 | 0.9 (4) |
O20—C6—C7—C8 | −178.5 (2) | N11—C12—C13—C14 | −179.1 (2) |
C5—C6—C7—C8 | 0.7 (4) | C12—C13—C14—C15 | 0.0 (4) |
O20—C6—C7—O22 | 0.4 (3) | C12—C13—C14—C18 | −177.0 (2) |
C5—C6—C7—O22 | 179.5 (2) | C13—C14—C15—C16 | −1.0 (4) |
O22—C7—C8—C9 | −178.3 (2) | C18—C14—C15—C16 | 176.0 (2) |
C6—C7—C8—C9 | 0.4 (4) | C14—C15—C16—C17 | 1.1 (4) |
C2—N1—C9—C10 | 1.0 (4) | C15—C16—C17—C12 | −0.2 (4) |
C2—N1—C9—C8 | −177.8 (2) | C13—C12—C17—C16 | −0.8 (4) |
C7—C8—C9—N1 | 177.4 (2) | N11—C12—C17—C16 | 179.3 (2) |
C7—C8—C9—C10 | −1.4 (4) | C5—C6—O20—C21 | −5.4 (4) |
N1—C9—C10—C5 | −177.5 (2) | C7—C6—O20—C21 | 173.7 (2) |
C8—C9—C10—C5 | 1.3 (3) | C8—C7—O22—C23 | 4.2 (4) |
N1—C9—C10—C4 | 0.8 (3) | C6—C7—O22—C23 | −174.5 (2) |
C8—C9—C10—C4 | 179.5 (2) | O24—C26—C27—C28 | 28.8 (4) |
C6—C5—C10—C9 | −0.2 (4) | O25—C26—C27—C28 | −151.9 (2) |
C6—C5—C10—C4 | −178.3 (2) | C26—C27—C28—C29 | −174.9 (2) |
N3—C4—C10—C9 | −2.6 (3) | C27—C28—C29—C30 | −177.6 (2) |
N11—C4—C10—C9 | 177.7 (2) | C28—C29—C30—C31 | −176.3 (2) |
N3—C4—C10—C5 | 175.5 (2) | C29—C30—C31—C31i | −179.2 (3) |
Symmetry code: (i) −x−1, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O24ii | 0.89 (3) | 2.15 (3) | 2.999 (3) | 160 (3) |
O25—H25···N1 | 0.98 (3) | 1.61 (3) | 2.592 (3) | 177 (4) |
Symmetry code: (ii) −x+1, −y+1, −z+1. |
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