organic compounds
4,4-Diphenyl-1-propyl-2-propylsulfanyl-4,5-dihydro-1H-imidazol-5-one
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: y.ramli@um5s.net.ma
In the title molecule, C21H24N2OS, the five-membered ring is planar with an r.m.s. deviation of 0.0142 Å. The phenyl rings are inclined to the plane of the dihydroimidazolone ring by 60.81 (6) and 79.23 (6)°. In the crystal, inversion dimers are formed by a C—H⋯O hydrogen bond and a C—H⋯π(ring) interaction. Additional C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions connect these dimers into chains along the c-axis direction.
CCDC reference: 1852189
Structure description
Over the past thirty years, imidazolone derivatives of hydantoin or thiohydantoin have been the focus of interest for the synthetic and pharmaceutical industries because of their biological properties. As part of our ongoing studies of 4,4- and 5,5-diphenylimidazolidine-2,4-dione and 5,5-diphenyl-2-thioxoimidazolidin-4-one 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.
In the title molecule (Fig. 1), the C10–C15 and C16–C21 benzene rings are inclined to the plane of the central five-membered ring by 60.81 (6) and 79.23 (6)°, respectively. In the crystal, C8—H8A⋯O1 hydrogen bonds and C9—H9A⋯Cg3 interactions, Table 1, form inversion dimers, which are connected into chains extending along the c-axis direction by C19—H19⋯O1 hydrogen bonds and C20—H20⋯Cg2 interactions (Table 1 and Fig. 2).
Synthesis and crystallization
Thiohydantoin (0.7 g) was placed in a flask with K2CO3 (0.9 g, 0.0065 mmol) in absolute dimethylformamide (DMF), and two equivalents of propyl iodide were added. The solution was left stirring for 2 h at room temperature. The solvent was then removed after filtration of the base and the oil obtained was recrystallized from methanol solution to yield colourless block-shaped single crystals (Guerrab et al., 2017c, 2018).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2
|
Structural data
CCDC reference: 1852189
https://doi.org/10.1107/S2414314618009343/sj4186sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618009343/sj4186Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618009343/sj4186Isup3.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: SHELXL2018 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C21H24N2OS | F(000) = 752 |
Mr = 352.48 | Dx = 1.266 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.898 (2) Å | Cell parameters from 9958 reflections |
b = 14.878 (2) Å | θ = 2.7–30.0° |
c = 8.4007 (13) Å | µ = 0.19 mm−1 |
β = 96.780 (2)° | T = 100 K |
V = 1849.0 (5) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.27 × 0.22 mm |
Bruker SMART APEX CCD diffractometer | 5241 independent reflections |
Radiation source: fine-focus sealed tube | 4279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 30.2°, θmin = 1.9° |
φ and ω scans | h = −21→21 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −20→20 |
Tmin = 0.84, Tmax = 0.96 | l = −11→11 |
35375 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | All H-atom parameters refined |
wR(F2) = 0.114 | w = 1/[σ2(Fo2) + (0.0755P)2 + 0.1235P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
5241 reflections | Δρmax = 0.51 e Å−3 |
322 parameters | Δρmin = −0.19 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 20 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.28969 (2) | 0.21368 (2) | 0.56491 (4) | 0.02040 (10) | |
O1 | 0.40566 (5) | 0.52459 (5) | 0.63859 (9) | 0.01851 (18) | |
N1 | 0.36245 (6) | 0.37573 (6) | 0.62527 (11) | 0.01618 (19) | |
N2 | 0.22807 (6) | 0.37922 (6) | 0.46398 (11) | 0.01469 (18) | |
C1 | 0.26378 (7) | 0.47263 (7) | 0.47678 (12) | 0.0131 (2) | |
C2 | 0.35317 (7) | 0.46531 (7) | 0.59014 (12) | 0.0146 (2) | |
C3 | 0.28811 (7) | 0.33033 (7) | 0.54480 (12) | 0.0153 (2) | |
C4 | 0.18745 (8) | 0.18173 (8) | 0.44041 (14) | 0.0203 (2) | |
H4A | 0.1989 (11) | 0.1189 (11) | 0.404 (2) | 0.037 (4)* | |
H4B | 0.1770 (12) | 0.2204 (10) | 0.342 (2) | 0.038 (5)* | |
C5 | 0.10239 (8) | 0.18493 (8) | 0.52482 (15) | 0.0217 (2) | |
H5A | 0.1147 (10) | 0.1580 (10) | 0.6326 (19) | 0.027 (4)* | |
H5B | 0.0847 (10) | 0.2504 (11) | 0.5396 (17) | 0.025 (3)* | |
C6 | 0.02608 (9) | 0.13272 (9) | 0.42926 (17) | 0.0264 (3) | |
H6A | 0.0410 (11) | 0.0673 (11) | 0.4339 (19) | 0.038 (4)* | |
H6B | 0.0169 (10) | 0.1538 (10) | 0.3164 (19) | 0.030 (4)* | |
H6C | −0.0330 (11) | 0.1417 (10) | 0.4759 (18) | 0.032 (4)* | |
C7 | 0.44183 (7) | 0.33597 (8) | 0.71897 (13) | 0.0181 (2) | |
H7A | 0.4663 (10) | 0.3808 (10) | 0.7962 (18) | 0.022 (3)* | |
H7B | 0.4168 (11) | 0.2821 (9) | 0.7763 (18) | 0.030 (4)* | |
C8 | 0.51335 (8) | 0.30657 (8) | 0.61454 (14) | 0.0189 (2) | |
H8A | 0.5325 (10) | 0.3615 (10) | 0.5576 (18) | 0.025 (4)* | |
H8B | 0.4848 (9) | 0.2635 (9) | 0.5348 (16) | 0.018 (3)* | |
C9 | 0.59323 (8) | 0.26092 (9) | 0.71236 (16) | 0.0232 (2) | |
H9A | 0.6227 (10) | 0.3009 (10) | 0.7940 (19) | 0.027 (4)* | |
H9B | 0.6360 (11) | 0.2419 (10) | 0.6369 (19) | 0.031 (4)* | |
H9C | 0.5719 (12) | 0.2071 (11) | 0.765 (2) | 0.038 (4)* | |
C10 | 0.19982 (7) | 0.53663 (7) | 0.54917 (12) | 0.0139 (2) | |
C11 | 0.11947 (7) | 0.50725 (7) | 0.59961 (13) | 0.0171 (2) | |
H11 | 0.1028 (9) | 0.4450 (10) | 0.5864 (17) | 0.022 (3)* | |
C12 | 0.06233 (8) | 0.56794 (8) | 0.66487 (14) | 0.0211 (2) | |
H12 | 0.0049 (10) | 0.5497 (10) | 0.7005 (17) | 0.024 (4)* | |
C13 | 0.08580 (8) | 0.65759 (8) | 0.68128 (14) | 0.0228 (2) | |
H13 | 0.0461 (10) | 0.6994 (10) | 0.7219 (18) | 0.025 (4)* | |
C14 | 0.16667 (9) | 0.68758 (8) | 0.63317 (15) | 0.0233 (2) | |
H14 | 0.1854 (10) | 0.7476 (10) | 0.6499 (17) | 0.023 (3)* | |
C15 | 0.22333 (8) | 0.62766 (7) | 0.56654 (14) | 0.0190 (2) | |
H15 | 0.2804 (10) | 0.6485 (10) | 0.5290 (17) | 0.025 (4)* | |
C16 | 0.28335 (7) | 0.50095 (7) | 0.30928 (12) | 0.0142 (2) | |
C17 | 0.36676 (8) | 0.48304 (7) | 0.25711 (14) | 0.0181 (2) | |
H17 | 0.4160 (10) | 0.4566 (10) | 0.3323 (17) | 0.027 (4)* | |
C18 | 0.38154 (9) | 0.50281 (8) | 0.10041 (14) | 0.0228 (3) | |
H18 | 0.4394 (11) | 0.4880 (11) | 0.0687 (19) | 0.038 (4)* | |
C19 | 0.31434 (9) | 0.54172 (8) | −0.00507 (14) | 0.0245 (3) | |
H19 | 0.3236 (10) | 0.5579 (10) | −0.1119 (19) | 0.033 (4)* | |
C20 | 0.23084 (9) | 0.55984 (8) | 0.04611 (14) | 0.0236 (2) | |
H20 | 0.1804 (11) | 0.5876 (11) | −0.026 (2) | 0.035 (4)* | |
C21 | 0.21515 (8) | 0.53930 (8) | 0.20199 (13) | 0.0189 (2) | |
H21 | 0.1559 (10) | 0.5492 (9) | 0.2374 (17) | 0.026 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02010 (16) | 0.01411 (15) | 0.02723 (17) | 0.00107 (9) | 0.00377 (12) | 0.00478 (10) |
O1 | 0.0172 (4) | 0.0200 (4) | 0.0179 (4) | −0.0018 (3) | 0.0004 (3) | −0.0023 (3) |
N1 | 0.0156 (4) | 0.0167 (4) | 0.0156 (4) | 0.0016 (3) | −0.0007 (3) | 0.0024 (3) |
N2 | 0.0165 (4) | 0.0126 (4) | 0.0154 (4) | −0.0007 (3) | 0.0036 (3) | 0.0000 (3) |
C1 | 0.0130 (5) | 0.0136 (5) | 0.0125 (5) | −0.0004 (3) | 0.0011 (4) | 0.0006 (3) |
C2 | 0.0155 (5) | 0.0179 (5) | 0.0108 (5) | 0.0010 (4) | 0.0030 (4) | 0.0000 (4) |
C3 | 0.0168 (5) | 0.0155 (5) | 0.0143 (5) | −0.0004 (4) | 0.0048 (4) | 0.0017 (4) |
C4 | 0.0239 (6) | 0.0158 (5) | 0.0219 (6) | −0.0021 (4) | 0.0061 (4) | −0.0009 (4) |
C5 | 0.0214 (6) | 0.0221 (6) | 0.0225 (6) | −0.0015 (4) | 0.0064 (5) | −0.0018 (5) |
C6 | 0.0243 (6) | 0.0254 (6) | 0.0296 (7) | −0.0039 (5) | 0.0038 (5) | −0.0027 (5) |
C7 | 0.0171 (5) | 0.0219 (5) | 0.0149 (5) | 0.0044 (4) | 0.0002 (4) | 0.0029 (4) |
C8 | 0.0180 (5) | 0.0226 (5) | 0.0159 (5) | 0.0016 (4) | 0.0018 (4) | 0.0016 (4) |
C9 | 0.0205 (6) | 0.0237 (6) | 0.0248 (6) | 0.0053 (5) | 0.0007 (5) | 0.0013 (5) |
C10 | 0.0146 (5) | 0.0158 (5) | 0.0110 (5) | 0.0015 (4) | 0.0005 (4) | 0.0011 (4) |
C11 | 0.0175 (5) | 0.0184 (5) | 0.0155 (5) | −0.0003 (4) | 0.0020 (4) | 0.0007 (4) |
C12 | 0.0173 (5) | 0.0277 (6) | 0.0187 (6) | 0.0029 (4) | 0.0044 (4) | 0.0015 (4) |
C13 | 0.0242 (6) | 0.0250 (6) | 0.0196 (6) | 0.0103 (5) | 0.0041 (5) | 0.0003 (4) |
C14 | 0.0281 (6) | 0.0160 (5) | 0.0258 (6) | 0.0030 (4) | 0.0036 (5) | −0.0014 (4) |
C15 | 0.0193 (5) | 0.0174 (5) | 0.0206 (6) | −0.0001 (4) | 0.0031 (4) | 0.0001 (4) |
C16 | 0.0175 (5) | 0.0129 (5) | 0.0122 (5) | −0.0025 (4) | 0.0023 (4) | −0.0003 (4) |
C17 | 0.0180 (5) | 0.0182 (5) | 0.0186 (5) | −0.0014 (4) | 0.0040 (4) | −0.0021 (4) |
C18 | 0.0252 (6) | 0.0240 (6) | 0.0209 (6) | −0.0065 (5) | 0.0105 (5) | −0.0063 (4) |
C19 | 0.0390 (7) | 0.0230 (6) | 0.0125 (5) | −0.0094 (5) | 0.0068 (5) | −0.0025 (4) |
C20 | 0.0311 (6) | 0.0238 (6) | 0.0146 (5) | −0.0026 (5) | −0.0024 (5) | 0.0012 (4) |
C21 | 0.0192 (5) | 0.0211 (5) | 0.0160 (5) | 0.0006 (4) | 0.0006 (4) | 0.0001 (4) |
S1—C3 | 1.7436 (11) | C9—H9A | 0.973 (16) |
S1—C4 | 1.8066 (13) | C9—H9B | 0.991 (16) |
O1—C2 | 1.2165 (13) | C9—H9C | 0.987 (16) |
N1—C2 | 1.3686 (14) | C10—C11 | 1.3867 (15) |
N1—C3 | 1.4012 (14) | C10—C15 | 1.4022 (15) |
N1—C7 | 1.4657 (14) | C11—C12 | 1.3967 (15) |
N2—C3 | 1.2832 (14) | C11—H11 | 0.961 (15) |
N2—C1 | 1.4874 (13) | C12—C13 | 1.3816 (18) |
C1—C10 | 1.5236 (14) | C12—H12 | 0.977 (14) |
C1—C16 | 1.5295 (14) | C13—C14 | 1.3889 (18) |
C1—C2 | 1.5469 (15) | C13—H13 | 0.949 (15) |
C4—C5 | 1.5242 (16) | C14—C15 | 1.3900 (16) |
C4—H4A | 1.003 (17) | C14—H14 | 0.941 (15) |
C4—H4B | 1.002 (17) | C15—H15 | 0.991 (14) |
C5—C6 | 1.5248 (18) | C16—C17 | 1.3914 (15) |
C5—H5A | 0.987 (15) | C16—C21 | 1.3978 (15) |
C5—H5B | 1.020 (16) | C17—C18 | 1.3915 (16) |
C6—H6A | 0.997 (17) | C17—H17 | 0.992 (15) |
C6—H6B | 0.993 (16) | C18—C19 | 1.3832 (19) |
C6—H6C | 1.014 (16) | C18—H18 | 0.958 (16) |
C7—C8 | 1.5222 (15) | C19—C20 | 1.3897 (18) |
C7—H7A | 0.971 (15) | C19—H19 | 0.955 (16) |
C7—H7B | 1.028 (15) | C20—C21 | 1.3911 (16) |
C8—C9 | 1.5238 (16) | C20—H20 | 0.997 (16) |
C8—H8A | 1.005 (15) | C21—H21 | 0.976 (15) |
C8—H8B | 0.987 (14) | ||
C3—S1—C4 | 101.83 (5) | C9—C8—H8B | 108.9 (8) |
C2—N1—C3 | 108.15 (9) | H8A—C8—H8B | 109.2 (11) |
C2—N1—C7 | 124.29 (9) | C8—C9—H9A | 111.5 (9) |
C3—N1—C7 | 127.32 (9) | C8—C9—H9B | 107.6 (9) |
C3—N2—C1 | 105.69 (9) | H9A—C9—H9B | 110.8 (13) |
N2—C1—C10 | 112.18 (8) | C8—C9—H9C | 109.4 (10) |
N2—C1—C16 | 107.23 (8) | H9A—C9—H9C | 108.7 (13) |
C10—C1—C16 | 113.03 (8) | H9B—C9—H9C | 108.8 (13) |
N2—C1—C2 | 104.68 (8) | C11—C10—C15 | 119.12 (10) |
C10—C1—C2 | 109.38 (8) | C11—C10—C1 | 121.87 (9) |
C16—C1—C2 | 110.00 (8) | C15—C10—C1 | 119.00 (9) |
O1—C2—N1 | 126.11 (10) | C10—C11—C12 | 120.28 (10) |
O1—C2—C1 | 128.88 (10) | C10—C11—H11 | 119.3 (8) |
N1—C2—C1 | 105.01 (8) | C12—C11—H11 | 120.4 (8) |
N2—C3—N1 | 116.35 (10) | C13—C12—C11 | 120.30 (11) |
N2—C3—S1 | 128.03 (8) | C13—C12—H12 | 117.3 (8) |
N1—C3—S1 | 115.61 (8) | C11—C12—H12 | 122.4 (8) |
C5—C4—S1 | 114.39 (8) | C12—C13—C14 | 119.94 (11) |
C5—C4—H4A | 110.5 (9) | C12—C13—H13 | 120.5 (9) |
S1—C4—H4A | 105.0 (9) | C14—C13—H13 | 119.6 (9) |
C5—C4—H4B | 107.9 (10) | C13—C14—C15 | 120.01 (11) |
S1—C4—H4B | 111.3 (10) | C13—C14—H14 | 120.9 (8) |
H4A—C4—H4B | 107.6 (13) | C15—C14—H14 | 119.0 (9) |
C4—C5—C6 | 110.39 (10) | C14—C15—C10 | 120.34 (11) |
C4—C5—H5A | 109.8 (8) | C14—C15—H15 | 120.8 (8) |
C6—C5—H5A | 108.8 (9) | C10—C15—H15 | 118.8 (8) |
C4—C5—H5B | 109.1 (8) | C17—C16—C21 | 118.90 (10) |
C6—C5—H5B | 111.3 (8) | C17—C16—C1 | 120.76 (9) |
H5A—C5—H5B | 107.3 (12) | C21—C16—C1 | 120.18 (9) |
C5—C6—H6A | 109.1 (9) | C16—C17—C18 | 120.30 (11) |
C5—C6—H6B | 110.6 (9) | C16—C17—H17 | 119.8 (8) |
H6A—C6—H6B | 110.6 (13) | C18—C17—H17 | 119.9 (8) |
C5—C6—H6C | 110.9 (9) | C19—C18—C17 | 120.74 (11) |
H6A—C6—H6C | 108.2 (12) | C19—C18—H18 | 121.7 (10) |
H6B—C6—H6C | 107.4 (12) | C17—C18—H18 | 117.5 (10) |
N1—C7—C8 | 112.44 (9) | C18—C19—C20 | 119.32 (11) |
N1—C7—H7A | 107.3 (9) | C18—C19—H19 | 122.3 (9) |
C8—C7—H7A | 110.4 (9) | C20—C19—H19 | 118.4 (9) |
N1—C7—H7B | 104.6 (9) | C19—C20—C21 | 120.30 (11) |
C8—C7—H7B | 111.3 (8) | C19—C20—H20 | 121.9 (9) |
H7A—C7—H7B | 110.6 (12) | C21—C20—H20 | 117.8 (9) |
C7—C8—C9 | 111.87 (9) | C20—C21—C16 | 120.44 (11) |
C7—C8—H8A | 107.4 (8) | C20—C21—H21 | 120.8 (9) |
C9—C8—H8A | 111.8 (9) | C16—C21—H21 | 118.7 (9) |
C7—C8—H8B | 107.6 (8) | ||
C3—N2—C1—C10 | −121.87 (9) | C16—C1—C10—C11 | 123.08 (10) |
C3—N2—C1—C16 | 113.47 (9) | C2—C1—C10—C11 | −114.01 (11) |
C3—N2—C1—C2 | −3.36 (10) | N2—C1—C10—C15 | −178.90 (9) |
C3—N1—C2—O1 | −179.50 (10) | C16—C1—C10—C15 | −57.51 (13) |
C7—N1—C2—O1 | −4.77 (17) | C2—C1—C10—C15 | 65.41 (12) |
C3—N1—C2—C1 | −0.08 (10) | C15—C10—C11—C12 | 0.83 (16) |
C7—N1—C2—C1 | 174.66 (9) | C1—C10—C11—C12 | −179.76 (10) |
N2—C1—C2—O1 | −178.56 (10) | C10—C11—C12—C13 | −0.67 (17) |
C10—C1—C2—O1 | −58.17 (13) | C11—C12—C13—C14 | −0.19 (18) |
C16—C1—C2—O1 | 66.53 (13) | C12—C13—C14—C15 | 0.89 (18) |
N2—C1—C2—N1 | 2.04 (10) | C13—C14—C15—C10 | −0.73 (18) |
C10—C1—C2—N1 | 122.43 (9) | C11—C10—C15—C14 | −0.13 (17) |
C16—C1—C2—N1 | −112.87 (9) | C1—C10—C15—C14 | −179.56 (10) |
C1—N2—C3—N1 | 3.68 (12) | N2—C1—C16—C17 | −88.04 (11) |
C1—N2—C3—S1 | −175.29 (8) | C10—C1—C16—C17 | 147.81 (10) |
C2—N1—C3—N2 | −2.40 (12) | C2—C1—C16—C17 | 25.24 (13) |
C7—N1—C3—N2 | −176.93 (10) | N2—C1—C16—C21 | 87.17 (11) |
C2—N1—C3—S1 | 176.70 (7) | C10—C1—C16—C21 | −36.98 (13) |
C7—N1—C3—S1 | 2.17 (14) | C2—C1—C16—C21 | −159.55 (9) |
C4—S1—C3—N2 | 1.13 (11) | C21—C16—C17—C18 | −0.24 (16) |
C4—S1—C3—N1 | −177.84 (8) | C1—C16—C17—C18 | 175.03 (10) |
C3—S1—C4—C5 | −85.29 (9) | C16—C17—C18—C19 | 1.00 (17) |
S1—C4—C5—C6 | −163.91 (9) | C17—C18—C19—C20 | −0.98 (17) |
C2—N1—C7—C8 | −90.02 (12) | C18—C19—C20—C21 | 0.20 (18) |
C3—N1—C7—C8 | 83.69 (13) | C19—C20—C21—C16 | 0.55 (18) |
N1—C7—C8—C9 | −177.00 (10) | C17—C16—C21—C20 | −0.53 (16) |
N2—C1—C10—C11 | 1.68 (14) | C1—C16—C21—C20 | −175.83 (10) |
Cg2 and Cg3 are the centroids of the C10–C15 and C16–C21 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8A···O1i | 1.005 (15) | 2.607 (15) | 3.5908 (14) | 166.2 (11) |
C9—H9A···Cg3i | 0.973 (16) | 2.908 (15) | 3.7370 (15) | 143.8 (12) |
C19—H19···O1ii | 0.955 (16) | 2.596 (16) | 3.4407 (15) | 147.7 (12) |
C20—H20···Cg2ii | 0.997 (16) | 2.999 (17) | 3.7390 (14) | 131.9 (12) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z−1. |
Funding information
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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