organic compounds
3-n-Pentyl-5,5-diphenylimidazolidine-2,4-dione
aLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: gerrab_walid@yahoo.com
In the title compound, C20H22N2O2, the central five-membered imidazolidine ring makes dihedral angles of 63.85 (6) and 70.38 (6)° with the two substituent phenyl rings. In the crystal, molecules form an inversion dimer through a pair of N—H⋯O hydrogen bonds. These are linked into a three-dimensional network via C—H⋯O hydrogen bonds. The n-pentyl chain is disordered over two sites, with an occupancy ratio of 0.876 (2):0.124 (2).
Keywords: crystal structure; hydrogen bond; imidazolidine-2,4-dione.
CCDC reference: 1587332
Structure description
As part of our ongoing studies of 5,5-diphenylimidazolidine-2,4-dione derivatives (Ramli, Akrad et al., 2017; Ramli, Guerrab et al., 2017; Akrad et al., 2017; Guerrab et al., 2017a,b), the title compound was prepared and its is reported here. The imidazolidine-2,4-dione ring has two phenyl groups attached at the 5-position (Fig. 1). The C4–C9 and C10–C15 rings are inclined to the five-membered ring by 70.38 (6) and 63.85 (6)°, respectively. In the crystal, a pair of N—H⋯O hydrogen bonds (N1—H1⋯O1i; symmetry code as in Table 1) link the molecules into an inversion dimer. The dimers are further linked into a three-dimensional network via C—H⋯O hydrogen bonds (C12—H12⋯O2ii and C14—H14⋯O2iii; Table 1 and Fig. 2). The structure consists of channels running along the a axis and having an approximately oval of ca 16.8 × 7.8 Å2 (Fig. 3).
Synthesis and crystallization
To a solution of 5,5-diphenylimidazolidine-2,4-dione (1 g, 3.96 mmol), one equivalent of pentyl bromide in absolute dimethylformamide (DMF) was added and the resulting solution heated under reflux for 3 h in the presence of 1.3 equivalents of K2CO3. The reaction mixture was filtered while hot, and the solvent evaporated under reduced pressure. The residue obtained was dried and crystallized from an ethanol solution to yield colourless block-shaped single crystals of the title compound.
Refinement
Crystal data, data collection and structure . The n-pentyl chain is disordered over two sites and the occupancy ratio was refined to 0.876 (2):0.124 (2). The geometries of the disordered components were restrained to be comparable. Constraints of the same anisotropic displacement parameters were also applied for the disordered non-H atoms.
details are summarized in Table 2Structural data
CCDC reference: 1587332
https://doi.org/10.1107/S2414314617016935/is4020sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016935/is4020Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617016935/is4020Isup3.cml
Data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Bruker, 2016).C20H22N2O2 | F(000) = 688 |
Mr = 322.39 | Dx = 1.246 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5949 (9) Å | Cell parameters from 9926 reflections |
b = 8.5931 (9) Å | θ = 2.4–29.2° |
c = 23.276 (2) Å | µ = 0.08 mm−1 |
β = 90.348 (2)° | T = 100 K |
V = 1719.1 (3) Å3 | Plate, colourless |
Z = 4 | 0.46 × 0.43 × 0.13 mm |
Bruker SMART APEX CCD diffractometer | 4644 independent reflections |
Radiation source: fine-focus sealed tube | 3849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.3°, θmin = 1.8° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −11→11 |
Tmin = 0.91, Tmax = 0.99 | l = −31→31 |
32274 measured reflections |
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)] = 0.047 | Hydrogen site location: mixed |
wR(F2) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0803P)2 + 0.3238P] where P = (Fo2 + 2Fc2)/3 |
4644 reflections | (Δ/σ)max < 0.001 |
236 parameters | Δρmax = 0.54 e Å−3 |
8 restraints | Δρmin = −0.38 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 sec/frame. |
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. |
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 > 2sigma(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.70156 (9) | 0.59673 (10) | 0.50462 (3) | 0.02237 (19) | |
O2 | 0.87704 (9) | 0.41015 (10) | 0.33272 (4) | 0.02262 (19) | |
N1 | 0.58128 (10) | 0.44972 (11) | 0.43413 (4) | 0.0180 (2) | |
H1 | 0.4913 (18) | 0.4382 (18) | 0.4518 (6) | 0.027 (4)* | |
N2 | 0.82575 (10) | 0.52328 (11) | 0.42027 (4) | 0.0178 (2) | |
C1 | 0.69930 (12) | 0.52957 (12) | 0.45825 (5) | 0.0168 (2) | |
C2 | 0.61887 (11) | 0.38545 (12) | 0.37780 (4) | 0.0158 (2) | |
C3 | 0.78989 (12) | 0.43843 (12) | 0.37198 (5) | 0.0170 (2) | |
C4 | 0.61088 (11) | 0.20752 (12) | 0.37723 (5) | 0.0171 (2) | |
C5 | 0.61400 (12) | 0.12283 (13) | 0.42812 (5) | 0.0212 (2) | |
H5 | 0.621107 | 0.175526 | 0.463921 | 0.025* | |
C6 | 0.60671 (14) | −0.03919 (14) | 0.42677 (5) | 0.0254 (3) | |
H6 | 0.609122 | −0.096649 | 0.461635 | 0.030* | |
C7 | 0.59598 (14) | −0.11648 (14) | 0.37474 (6) | 0.0262 (3) | |
H7 | 0.588795 | −0.226785 | 0.373962 | 0.031* | |
C8 | 0.59569 (14) | −0.03291 (14) | 0.32362 (6) | 0.0257 (3) | |
H8 | 0.590429 | −0.086110 | 0.287885 | 0.031* | |
C9 | 0.60312 (13) | 0.12879 (13) | 0.32486 (5) | 0.0215 (2) | |
H9 | 0.602914 | 0.185852 | 0.289907 | 0.026* | |
C10 | 0.51272 (12) | 0.45835 (12) | 0.33207 (4) | 0.0160 (2) | |
C11 | 0.35237 (13) | 0.44099 (13) | 0.33893 (5) | 0.0213 (2) | |
H11 | 0.313738 | 0.380959 | 0.370002 | 0.026* | |
C12 | 0.24873 (13) | 0.51060 (15) | 0.30077 (5) | 0.0253 (2) | |
H12 | 0.139838 | 0.498098 | 0.305787 | 0.030* | |
C13 | 0.30454 (14) | 0.59832 (15) | 0.25538 (6) | 0.0274 (3) | |
H13 | 0.233993 | 0.647602 | 0.229603 | 0.033* | |
C14 | 0.46365 (14) | 0.61397 (15) | 0.24768 (5) | 0.0282 (3) | |
H14 | 0.501879 | 0.672776 | 0.216217 | 0.034* | |
C15 | 0.56768 (13) | 0.54401 (14) | 0.28578 (5) | 0.0229 (2) | |
H15 | 0.676517 | 0.554837 | 0.280135 | 0.027* | |
C16 | 0.97712 (12) | 0.59637 (14) | 0.43206 (5) | 0.0234 (2) | 0.876 (2) |
H16A | 1.060263 | 0.526078 | 0.418348 | 0.028* | 0.876 (2) |
H16B | 0.989924 | 0.607509 | 0.474154 | 0.028* | 0.876 (2) |
C17 | 0.99889 (15) | 0.75387 (15) | 0.40460 (7) | 0.0243 (3) | 0.876 (2) |
H17A | 0.912726 | 0.823496 | 0.416073 | 0.029* | 0.876 (2) |
H17B | 0.995667 | 0.742857 | 0.362273 | 0.029* | 0.876 (2) |
C18 | 1.15373 (14) | 0.82592 (16) | 0.42272 (7) | 0.0253 (3) | 0.876 (2) |
H18A | 1.157565 | 0.833338 | 0.465144 | 0.030* | 0.876 (2) |
H18B | 1.239395 | 0.756659 | 0.410473 | 0.030* | 0.876 (2) |
C19 | 1.17926 (16) | 0.98717 (18) | 0.39724 (7) | 0.0315 (3) | 0.876 (2) |
H19A | 1.170114 | 0.980564 | 0.354896 | 0.038* | 0.876 (2) |
H19B | 1.286242 | 1.021956 | 0.406625 | 0.038* | 0.876 (2) |
C20 | 1.0637 (3) | 1.1084 (2) | 0.41924 (13) | 0.0403 (5) | 0.876 (2) |
H20A | 1.086008 | 1.209360 | 0.401548 | 0.061* | 0.876 (2) |
H20B | 1.073526 | 1.117197 | 0.461086 | 0.061* | 0.876 (2) |
H20C | 0.957600 | 1.076219 | 0.409194 | 0.061* | 0.876 (2) |
C16A | 0.97712 (12) | 0.59637 (14) | 0.43206 (5) | 0.0234 (2) | 0.124 (2) |
H16C | 1.062281 | 0.519706 | 0.427870 | 0.028* | 0.124 (2) |
H16D | 0.980364 | 0.639019 | 0.471557 | 0.028* | 0.124 (2) |
C17A | 0.9931 (9) | 0.7259 (9) | 0.3882 (3) | 0.0243 (3) | 0.124 (2) |
H17C | 0.910011 | 0.803538 | 0.394727 | 0.029* | 0.124 (2) |
H17D | 0.977141 | 0.681752 | 0.349278 | 0.029* | 0.124 (2) |
C18A | 1.1499 (8) | 0.8083 (8) | 0.3900 (4) | 0.0253 (3) | 0.124 (2) |
H18C | 1.232160 | 0.730682 | 0.398215 | 0.030* | 0.124 (2) |
H18D | 1.170922 | 0.853276 | 0.351630 | 0.030* | 0.124 (2) |
C19A | 1.1596 (11) | 0.9373 (10) | 0.4346 (4) | 0.0315 (3) | 0.124 (2) |
H19C | 1.269877 | 0.952670 | 0.445714 | 0.038* | 0.124 (2) |
H19D | 1.102479 | 0.904136 | 0.469368 | 0.038* | 0.124 (2) |
C20A | 1.093 (3) | 1.0922 (12) | 0.4137 (10) | 0.0403 (5) | 0.124 (2) |
H20D | 1.150894 | 1.127650 | 0.380078 | 0.061* | 0.124 (2) |
H20E | 1.101665 | 1.169795 | 0.444423 | 0.061* | 0.124 (2) |
H20F | 0.983034 | 1.078467 | 0.403273 | 0.061* | 0.124 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0187 (4) | 0.0286 (4) | 0.0199 (4) | −0.0031 (3) | 0.0018 (3) | −0.0075 (3) |
O2 | 0.0168 (4) | 0.0281 (4) | 0.0230 (4) | −0.0014 (3) | 0.0074 (3) | −0.0041 (3) |
N1 | 0.0139 (4) | 0.0234 (5) | 0.0169 (4) | −0.0037 (3) | 0.0042 (3) | −0.0052 (3) |
N2 | 0.0128 (4) | 0.0208 (4) | 0.0200 (4) | −0.0026 (3) | 0.0029 (3) | −0.0030 (3) |
C1 | 0.0139 (4) | 0.0180 (5) | 0.0185 (5) | −0.0003 (3) | 0.0019 (4) | −0.0014 (4) |
C2 | 0.0137 (4) | 0.0185 (5) | 0.0151 (5) | −0.0021 (3) | 0.0040 (3) | −0.0031 (4) |
C3 | 0.0143 (4) | 0.0174 (5) | 0.0193 (5) | −0.0008 (3) | 0.0025 (4) | −0.0003 (4) |
C4 | 0.0130 (4) | 0.0183 (5) | 0.0200 (5) | −0.0009 (3) | 0.0022 (4) | −0.0004 (4) |
C5 | 0.0190 (5) | 0.0241 (5) | 0.0206 (5) | −0.0010 (4) | 0.0003 (4) | 0.0015 (4) |
C6 | 0.0241 (6) | 0.0240 (6) | 0.0280 (6) | 0.0011 (4) | 0.0023 (4) | 0.0068 (4) |
C7 | 0.0242 (6) | 0.0187 (5) | 0.0357 (7) | 0.0021 (4) | 0.0032 (5) | 0.0005 (4) |
C8 | 0.0289 (6) | 0.0207 (6) | 0.0276 (6) | 0.0021 (4) | 0.0019 (5) | −0.0054 (4) |
C9 | 0.0239 (5) | 0.0204 (5) | 0.0203 (5) | 0.0008 (4) | 0.0022 (4) | −0.0017 (4) |
C10 | 0.0166 (5) | 0.0150 (5) | 0.0165 (5) | −0.0013 (3) | 0.0015 (4) | −0.0028 (4) |
C11 | 0.0168 (5) | 0.0245 (5) | 0.0226 (5) | −0.0016 (4) | 0.0036 (4) | 0.0017 (4) |
C12 | 0.0171 (5) | 0.0312 (6) | 0.0277 (6) | 0.0009 (4) | 0.0009 (4) | 0.0002 (5) |
C13 | 0.0260 (6) | 0.0285 (6) | 0.0278 (6) | 0.0014 (4) | −0.0043 (5) | 0.0039 (5) |
C14 | 0.0286 (6) | 0.0311 (6) | 0.0249 (6) | −0.0077 (5) | −0.0008 (5) | 0.0086 (5) |
C15 | 0.0186 (5) | 0.0271 (6) | 0.0230 (6) | −0.0059 (4) | 0.0029 (4) | 0.0018 (4) |
C16 | 0.0137 (5) | 0.0272 (6) | 0.0293 (6) | −0.0034 (4) | 0.0004 (4) | −0.0044 (5) |
C17 | 0.0178 (5) | 0.0221 (6) | 0.0330 (8) | −0.0044 (5) | −0.0019 (5) | −0.0039 (6) |
C18 | 0.0157 (5) | 0.0267 (7) | 0.0334 (8) | −0.0048 (5) | −0.0028 (5) | −0.0018 (6) |
C19 | 0.0198 (6) | 0.0308 (7) | 0.0440 (9) | −0.0077 (5) | 0.0029 (6) | 0.0045 (6) |
C20 | 0.0269 (13) | 0.0265 (7) | 0.0677 (13) | −0.0030 (6) | 0.0068 (9) | −0.0033 (8) |
C16A | 0.0137 (5) | 0.0272 (6) | 0.0293 (6) | −0.0034 (4) | 0.0004 (4) | −0.0044 (5) |
C17A | 0.0178 (5) | 0.0221 (6) | 0.0330 (8) | −0.0044 (5) | −0.0019 (5) | −0.0039 (6) |
C18A | 0.0157 (5) | 0.0267 (7) | 0.0334 (8) | −0.0048 (5) | −0.0028 (5) | −0.0018 (6) |
C19A | 0.0198 (6) | 0.0308 (7) | 0.0440 (9) | −0.0077 (5) | 0.0029 (6) | 0.0045 (6) |
C20A | 0.0269 (13) | 0.0265 (7) | 0.0677 (13) | −0.0030 (6) | 0.0068 (9) | −0.0033 (8) |
O1—C1 | 1.2238 (13) | C14—H14 | 0.9500 |
O2—C3 | 1.2098 (13) | C15—H15 | 0.9500 |
N1—C1 | 1.3447 (13) | C16—C17 | 1.5088 (18) |
N1—C2 | 1.4608 (13) | C16—H16A | 0.9900 |
N1—H1 | 0.884 (16) | C16—H16B | 0.9900 |
N2—C3 | 1.3732 (14) | C17—C18 | 1.5250 (17) |
N2—C1 | 1.4062 (13) | C17—H17A | 0.9900 |
N2—C16A | 1.4690 (13) | C17—H17B | 0.9900 |
N2—C16 | 1.4690 (13) | C18—C19 | 1.523 (2) |
C2—C4 | 1.5305 (15) | C18—H18A | 0.9900 |
C2—C10 | 1.5316 (15) | C18—H18B | 0.9900 |
C2—C3 | 1.5455 (14) | C19—C20 | 1.529 (2) |
C4—C5 | 1.3904 (15) | C19—H19A | 0.9900 |
C4—C9 | 1.3953 (15) | C19—H19B | 0.9900 |
C5—C6 | 1.3940 (17) | C20—H20A | 0.9800 |
C5—H5 | 0.9500 | C20—H20B | 0.9800 |
C6—C7 | 1.3839 (18) | C20—H20C | 0.9800 |
C6—H6 | 0.9500 | C16A—C17A | 1.518 (3) |
C7—C8 | 1.3898 (18) | C16A—H16C | 0.9900 |
C7—H7 | 0.9500 | C16A—H16D | 0.9900 |
C8—C9 | 1.3913 (16) | C17A—C18A | 1.523 (3) |
C8—H8 | 0.9500 | C17A—H17C | 0.9900 |
C9—H9 | 0.9500 | C17A—H17D | 0.9900 |
C10—C15 | 1.3899 (15) | C18A—C19A | 1.521 (4) |
C10—C11 | 1.3964 (14) | C18A—H18C | 0.9900 |
C11—C12 | 1.3894 (16) | C18A—H18D | 0.9900 |
C11—H11 | 0.9500 | C19A—C20A | 1.528 (4) |
C12—C13 | 1.3859 (18) | C19A—H19C | 0.9900 |
C12—H12 | 0.9500 | C19A—H19D | 0.9900 |
C13—C14 | 1.3868 (17) | C20A—H20D | 0.9800 |
C13—H13 | 0.9500 | C20A—H20E | 0.9800 |
C14—C15 | 1.3920 (17) | C20A—H20F | 0.9800 |
C1—N1—C2 | 113.42 (8) | N2—C16—H16B | 108.6 |
C1—N1—H1 | 121.5 (10) | C17—C16—H16B | 108.6 |
C2—N1—H1 | 125.0 (10) | H16A—C16—H16B | 107.6 |
C3—N2—C1 | 111.38 (8) | C16—C17—C18 | 110.94 (11) |
C3—N2—C16 | 125.03 (9) | C16—C17—H17A | 109.5 |
C1—N2—C16 | 123.58 (9) | C18—C17—H17A | 109.5 |
O1—C1—N1 | 128.08 (10) | C16—C17—H17B | 109.5 |
O1—C1—N2 | 124.36 (9) | C18—C17—H17B | 109.5 |
N1—C1—N2 | 107.56 (9) | H17A—C17—H17B | 108.0 |
N1—C2—C4 | 112.04 (9) | C19—C18—C17 | 112.90 (11) |
N1—C2—C10 | 109.58 (8) | C19—C18—H18A | 109.0 |
C4—C2—C10 | 112.09 (8) | C17—C18—H18A | 109.0 |
N1—C2—C3 | 100.53 (8) | C19—C18—H18B | 109.0 |
C4—C2—C3 | 109.64 (8) | C17—C18—H18B | 109.0 |
C10—C2—C3 | 112.43 (8) | H18A—C18—H18B | 107.8 |
O2—C3—N2 | 126.02 (10) | C18—C19—C20 | 113.19 (15) |
O2—C3—C2 | 126.90 (10) | C18—C19—H19A | 108.9 |
N2—C3—C2 | 107.07 (8) | C20—C19—H19A | 108.9 |
C5—C4—C9 | 119.41 (10) | C18—C19—H19B | 108.9 |
C5—C4—C2 | 121.00 (10) | C20—C19—H19B | 108.9 |
C9—C4—C2 | 119.59 (9) | H19A—C19—H19B | 107.8 |
C4—C5—C6 | 120.20 (11) | C19—C20—H20A | 109.5 |
C4—C5—H5 | 119.9 | C19—C20—H20B | 109.5 |
C6—C5—H5 | 119.9 | H20A—C20—H20B | 109.5 |
C7—C6—C5 | 120.12 (11) | C19—C20—H20C | 109.5 |
C7—C6—H6 | 119.9 | H20A—C20—H20C | 109.5 |
C5—C6—H6 | 119.9 | H20B—C20—H20C | 109.5 |
C6—C7—C8 | 120.07 (11) | N2—C16A—C17A | 105.8 (3) |
C6—C7—H7 | 120.0 | N2—C16A—H16C | 110.6 |
C8—C7—H7 | 120.0 | C17A—C16A—H16C | 110.6 |
C7—C8—C9 | 119.90 (11) | N2—C16A—H16D | 110.6 |
C7—C8—H8 | 120.1 | C17A—C16A—H16D | 110.6 |
C9—C8—H8 | 120.1 | H16C—C16A—H16D | 108.7 |
C8—C9—C4 | 120.29 (11) | C16A—C17A—C18A | 114.0 (4) |
C8—C9—H9 | 119.9 | C16A—C17A—H17C | 108.8 |
C4—C9—H9 | 119.9 | C18A—C17A—H17C | 108.8 |
C15—C10—C11 | 119.04 (10) | C16A—C17A—H17D | 108.8 |
C15—C10—C2 | 123.47 (9) | C18A—C17A—H17D | 108.8 |
C11—C10—C2 | 117.46 (9) | H17C—C17A—H17D | 107.7 |
C12—C11—C10 | 120.69 (10) | C19A—C18A—C17A | 113.7 (4) |
C12—C11—H11 | 119.7 | C19A—C18A—H18C | 108.8 |
C10—C11—H11 | 119.7 | C17A—C18A—H18C | 108.8 |
C13—C12—C11 | 119.86 (11) | C19A—C18A—H18D | 108.8 |
C13—C12—H12 | 120.1 | C17A—C18A—H18D | 108.8 |
C11—C12—H12 | 120.1 | H18C—C18A—H18D | 107.7 |
C12—C13—C14 | 119.83 (11) | C18A—C19A—C20A | 113.5 (5) |
C12—C13—H13 | 120.1 | C18A—C19A—H19C | 108.9 |
C14—C13—H13 | 120.1 | C20A—C19A—H19C | 108.9 |
C13—C14—C15 | 120.39 (11) | C18A—C19A—H19D | 108.9 |
C13—C14—H14 | 119.8 | C20A—C19A—H19D | 108.9 |
C15—C14—H14 | 119.8 | H19C—C19A—H19D | 107.7 |
C10—C15—C14 | 120.17 (10) | C19A—C20A—H20D | 109.5 |
C10—C15—H15 | 119.9 | C19A—C20A—H20E | 109.5 |
C14—C15—H15 | 119.9 | H20D—C20A—H20E | 109.5 |
N2—C16—C17 | 114.61 (10) | C19A—C20A—H20F | 109.5 |
N2—C16—H16A | 108.6 | H20D—C20A—H20F | 109.5 |
C17—C16—H16A | 108.6 | H20E—C20A—H20F | 109.5 |
C2—N1—C1—O1 | 179.44 (11) | C4—C5—C6—C7 | −0.15 (17) |
C2—N1—C1—N2 | −0.74 (12) | C5—C6—C7—C8 | 1.34 (17) |
C3—N2—C1—O1 | 179.30 (10) | C6—C7—C8—C9 | −1.27 (17) |
C16A—N2—C1—O1 | 0.42 (17) | C7—C8—C9—C4 | 0.01 (17) |
C16—N2—C1—O1 | 0.42 (17) | C5—C4—C9—C8 | 1.17 (16) |
C3—N2—C1—N1 | −0.53 (12) | C2—C4—C9—C8 | −179.95 (10) |
C16A—N2—C1—N1 | −179.41 (10) | N1—C2—C10—C15 | 119.65 (11) |
C16—N2—C1—N1 | −179.41 (10) | C4—C2—C10—C15 | −115.31 (11) |
C1—N1—C2—C4 | 117.89 (10) | C3—C2—C10—C15 | 8.75 (14) |
C1—N1—C2—C10 | −117.03 (10) | N1—C2—C10—C11 | −58.20 (12) |
C1—N1—C2—C3 | 1.52 (11) | C4—C2—C10—C11 | 66.84 (12) |
C1—N2—C3—O2 | −178.01 (11) | C3—C2—C10—C11 | −169.10 (9) |
C16A—N2—C3—O2 | 0.85 (18) | C15—C10—C11—C12 | −1.22 (17) |
C16—N2—C3—O2 | 0.85 (18) | C2—C10—C11—C12 | 176.73 (10) |
C1—N2—C3—C2 | 1.48 (12) | C10—C11—C12—C13 | −0.02 (18) |
C16A—N2—C3—C2 | −179.66 (10) | C11—C12—C13—C14 | 1.11 (19) |
C16—N2—C3—C2 | −179.66 (10) | C12—C13—C14—C15 | −1.0 (2) |
N1—C2—C3—O2 | 177.74 (11) | C11—C10—C15—C14 | 1.37 (17) |
C4—C2—C3—O2 | 59.60 (14) | C2—C10—C15—C14 | −176.45 (10) |
C10—C2—C3—O2 | −65.80 (14) | C13—C14—C15—C10 | −0.29 (19) |
N1—C2—C3—N2 | −1.74 (11) | C3—N2—C16—C17 | 83.71 (14) |
C4—C2—C3—N2 | −119.88 (9) | C1—N2—C16—C17 | −97.57 (13) |
C10—C2—C3—N2 | 114.71 (10) | N2—C16—C17—C18 | 175.78 (10) |
N1—C2—C4—C5 | −17.72 (13) | C16—C17—C18—C19 | −178.55 (12) |
C10—C2—C4—C5 | −141.40 (10) | C17—C18—C19—C20 | 65.5 (2) |
C3—C2—C4—C5 | 93.00 (11) | C3—N2—C16A—C17A | 67.9 (5) |
N1—C2—C4—C9 | 163.42 (9) | C1—N2—C16A—C17A | −113.4 (5) |
C10—C2—C4—C9 | 39.74 (13) | N2—C16A—C17A—C18A | −175.2 (5) |
C3—C2—C4—C9 | −85.86 (11) | C16A—C17A—C18A—C19A | −84.2 (9) |
C9—C4—C5—C6 | −1.10 (16) | C17A—C18A—C19A—C20A | −83.6 (13) |
C2—C4—C5—C6 | −179.96 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.884 (16) | 1.972 (16) | 2.8538 (12) | 175.9 (15) |
C12—H12···O2ii | 0.95 | 2.47 | 3.3960 (14) | 166 |
C14—H14···O2iii | 0.95 | 2.56 | 3.4475 (15) | 156 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1, y, z; (iii) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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