organic compounds
Ethyl 2-(2,5-dioxo-4,4-diphenylimidazolidin-1-yl)acetate
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: rakrad@yahoo.com
The five-membered ring of the title compound, C19H18N2O4, adopts an In the crystal, pairwise N—H⋯O hydrogen bonds form centrosymmetric dimers which are connected into chains parallel to the c-axis direction by pairwise C—H⋯O hydrogen bonds. A second set of C—H⋯O hydrogen bonds links these chains into sheets oriented parallel to (100). A combination of additional C—H⋯O hydrogen bonds and C—H⋯π(ring) interactions combine the sheets into a three-dimensional network.
Keywords: crystal structure; imidazole; hydrogen bonds.
CCDC reference: 1528488
Structure description
An enormous variety of hydantoin derivatives with varied pharmaceutical and medicinal applications, have been reported (Weichet, 1974; Havera & Strycker, 1976; Khodair et al., 1997; Thenmozhiyal et al., 2004). As a continuation of our research into hydantoin derivatives (Akrad et al. 2017), the title compound (Fig. 1) was prepared and its molecular and is reported here.
A puckering analysis of the five-membered ring gave the parameters Q(2) = 0.0712 (16) Å and φ(2) = 279.3 (13)°. The conformation of the ring is best described as an envelope on C1. The dihedral angle between the C4–C9 benzene ring and the mean plane of the five-membered ring is 80.56 (6)°, while the corresponding angle for the C10–C15 ring is 61.79 (4)°.
In the crystal, the molecules form centrosymmetric dimers through complementary N1—H1⋯O2 hydrogen bonds. The dimers are linked into chains running parallel to the c-axis direction by pairwise C15—H15⋯O1 hydrogen bonds (Table 1 and Figs. 2 and 3). The chains are formed into sheets oriented parallel to (100) by C16—H16A⋯O4 hydrogen bonds (Table 2 and Figs. 2 and 3) while the sheets are associated by a combination of C18—H18A⋯O3 hydrogen bonds and C7—H7⋯π(Cg3) interactions (Table 1 and Figs. 2 and 3). The packing is further aided by C12—H12⋯π(Cg2) and C19—H19⋯π(Cg2) (interactions (Table 2 and Figs. 2 and 3).
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Synthesis and crystallization
To a solution of 5,5-diphenylimidazolidine-2,4-dione (3.96 mol, 1 g) in 20 ml of ethanol was added ethyl bromoacetate (3.96 mol, 438 mm l), K2CO3 (3.96 mol) and a catalytic amount of tetrabutylammonium bromide. The mixture was stirred at room temperature for 24 h. Progress was monitored by TLC and, when complete, the solid material was removed by filtration and the solvent evaporated under vacuum. The solid product was purified by recrystallization from ethanol solution to afford colourless block-like crystals of the title compound (yield 67%).
Refinement
Crystal data, data collection and structure . Analysis of the 1461 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008a) showed the crystal to belong to the triclinic system and to consist of two major and at least two minor components. Since 91% of the reflections could be indexed on the two major components, it was decided to treat the crystal as having two components. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.
details are summarized in Table 2Structural data
CCDC reference: 1528488
https://doi.org/10.1107/S2414314617000980/sj4081sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617000980/sj4081Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617000980/sj4081Isup3.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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).C19H18N2O4 | Z = 2 |
Mr = 338.35 | F(000) = 356 |
Triclinic, P1 | Dx = 1.351 Mg m−3 |
a = 8.5041 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.6959 (5) Å | Cell parameters from 9879 reflections |
c = 12.5024 (8) Å | θ = 2.6–29.1° |
α = 71.002 (1)° | µ = 0.10 mm−1 |
β = 88.165 (1)° | T = 100 K |
γ = 72.572 (1)° | Column, colourless |
V = 831.87 (9) Å3 | 0.43 × 0.29 × 0.26 mm |
Bruker SMART APEX CCD diffractometer | 31786 independent reflections |
Radiation source: fine-focus sealed tube | 21954 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.2°, θmin = 1.7° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009) | k = −11→11 |
Tmin = 0.96, Tmax = 0.97 | l = −17→17 |
31786 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: difference Fourier map |
wR(F2) = 0.130 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.0554P] where P = (Fo2 + 2Fc2)/3 |
31786 reflections | (Δ/σ)max < 0.001 |
299 parameters | Δρmax = 0.51 e Å−3 |
0 restraints | Δρmin = −0.32 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 7.5 sec/frame. Analysis of 1461 reflections having I/σ(I) > 13 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the triclinic system and to consist of two major and at least two minor components. Since 91% of the reflections could be indexed on the two major components, it was decided to treat the crystal as having tw components. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW. |
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. The structure was refined as a two-component twin. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.66938 (14) | 0.42374 (14) | 0.40959 (9) | 0.0212 (3) | |
O2 | 0.48505 (14) | 0.30571 (14) | 0.11562 (9) | 0.0236 (3) | |
O3 | 0.85782 (14) | 0.08216 (15) | 0.34383 (10) | 0.0273 (3) | |
O4 | 0.73722 (13) | −0.10111 (13) | 0.46031 (9) | 0.0205 (3) | |
N1 | 0.54197 (16) | 0.54676 (16) | 0.12269 (11) | 0.0163 (3) | |
H1 | 0.534 (2) | 0.603 (2) | 0.0466 (17) | 0.033 (5)* | |
N2 | 0.55850 (16) | 0.33561 (16) | 0.28322 (10) | 0.0168 (3) | |
C1 | 0.61488 (18) | 0.44787 (19) | 0.31540 (12) | 0.0160 (3) | |
C2 | 0.52414 (18) | 0.39103 (19) | 0.16561 (13) | 0.0165 (3) | |
C3 | 0.59387 (18) | 0.60646 (19) | 0.20887 (12) | 0.0143 (3) | |
C4 | 0.75973 (18) | 0.64172 (19) | 0.18369 (12) | 0.0157 (3) | |
C5 | 0.8844 (2) | 0.5282 (2) | 0.14690 (14) | 0.0207 (3) | |
H5 | 0.862 (2) | 0.428 (2) | 0.1372 (15) | 0.025 (5)* | |
C6 | 1.0353 (2) | 0.5584 (2) | 0.12179 (14) | 0.0249 (4) | |
H6 | 1.121 (2) | 0.476 (2) | 0.0956 (15) | 0.029 (5)* | |
C7 | 1.0626 (2) | 0.7013 (2) | 0.13345 (15) | 0.0270 (4) | |
H7 | 1.171 (2) | 0.725 (2) | 0.1153 (16) | 0.036 (5)* | |
C8 | 0.9406 (2) | 0.8130 (2) | 0.17129 (15) | 0.0272 (4) | |
H8 | 0.956 (2) | 0.912 (2) | 0.1786 (16) | 0.035 (5)* | |
C9 | 0.7894 (2) | 0.7831 (2) | 0.19693 (14) | 0.0218 (4) | |
H9 | 0.702 (2) | 0.864 (2) | 0.2216 (15) | 0.026 (5)* | |
C10 | 0.45633 (18) | 0.76081 (19) | 0.21919 (13) | 0.0151 (3) | |
C11 | 0.3922 (2) | 0.8989 (2) | 0.12049 (14) | 0.0190 (3) | |
H11 | 0.437 (2) | 0.894 (2) | 0.0486 (15) | 0.021 (4)* | |
C12 | 0.2686 (2) | 1.0425 (2) | 0.12466 (15) | 0.0219 (4) | |
H12 | 0.222 (2) | 1.140 (2) | 0.0536 (15) | 0.027 (5)* | |
C13 | 0.2049 (2) | 1.0487 (2) | 0.22742 (14) | 0.0218 (4) | |
H13 | 0.117 (2) | 1.150 (2) | 0.2302 (14) | 0.025 (5)* | |
C14 | 0.2662 (2) | 0.9111 (2) | 0.32521 (15) | 0.0223 (4) | |
H14 | 0.220 (2) | 0.911 (2) | 0.3975 (16) | 0.028 (5)* | |
C15 | 0.3926 (2) | 0.7678 (2) | 0.32182 (14) | 0.0191 (3) | |
H15 | 0.436 (2) | 0.676 (2) | 0.3905 (15) | 0.024 (5)* | |
C16 | 0.5624 (2) | 0.1679 (2) | 0.35767 (14) | 0.0185 (3) | |
H16A | 0.515 (2) | 0.177 (2) | 0.4279 (16) | 0.025 (5)* | |
H16B | 0.497 (2) | 0.126 (2) | 0.3197 (15) | 0.026 (5)* | |
C17 | 0.73753 (19) | 0.0476 (2) | 0.38441 (13) | 0.0180 (3) | |
C18 | 0.8993 (2) | −0.2297 (2) | 0.50004 (16) | 0.0238 (4) | |
H18A | 0.964 (2) | −0.185 (2) | 0.5386 (15) | 0.026 (5)* | |
H18B | 0.955 (2) | −0.249 (2) | 0.4347 (16) | 0.027 (5)* | |
C19 | 0.8664 (2) | −0.3865 (2) | 0.57850 (17) | 0.0293 (4) | |
H19A | 0.977 (3) | −0.481 (3) | 0.6116 (17) | 0.039 (6)* | |
H19B | 0.801 (3) | −0.364 (2) | 0.6446 (17) | 0.039 (6)* | |
H19C | 0.799 (3) | −0.430 (2) | 0.5386 (17) | 0.039 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0269 (6) | 0.0215 (6) | 0.0139 (6) | −0.0064 (5) | −0.0011 (4) | −0.0048 (5) |
O2 | 0.0338 (7) | 0.0224 (6) | 0.0201 (6) | −0.0164 (5) | 0.0009 (5) | −0.0072 (5) |
O3 | 0.0228 (6) | 0.0235 (7) | 0.0349 (7) | −0.0082 (5) | 0.0108 (5) | −0.0087 (5) |
O4 | 0.0216 (6) | 0.0148 (6) | 0.0212 (6) | −0.0043 (4) | 0.0010 (4) | −0.0018 (5) |
N1 | 0.0224 (7) | 0.0167 (7) | 0.0116 (6) | −0.0089 (5) | 0.0002 (5) | −0.0042 (5) |
N2 | 0.0217 (7) | 0.0142 (7) | 0.0142 (6) | −0.0080 (5) | 0.0010 (5) | −0.0020 (5) |
C1 | 0.0159 (7) | 0.0163 (8) | 0.0150 (7) | −0.0040 (6) | 0.0029 (5) | −0.0054 (6) |
C2 | 0.0164 (7) | 0.0174 (8) | 0.0161 (7) | −0.0066 (6) | 0.0012 (6) | −0.0048 (6) |
C3 | 0.0177 (7) | 0.0153 (8) | 0.0112 (7) | −0.0070 (6) | 0.0011 (5) | −0.0046 (6) |
C4 | 0.0183 (7) | 0.0176 (8) | 0.0113 (7) | −0.0073 (6) | 0.0006 (5) | −0.0031 (6) |
C5 | 0.0216 (8) | 0.0192 (8) | 0.0209 (8) | −0.0065 (6) | 0.0015 (6) | −0.0060 (7) |
C6 | 0.0190 (8) | 0.0295 (10) | 0.0241 (9) | −0.0048 (7) | 0.0028 (6) | −0.0085 (8) |
C7 | 0.0197 (8) | 0.0365 (11) | 0.0258 (9) | −0.0144 (8) | 0.0017 (7) | −0.0064 (8) |
C8 | 0.0271 (9) | 0.0302 (10) | 0.0321 (10) | −0.0171 (8) | 0.0018 (7) | −0.0130 (8) |
C9 | 0.0218 (8) | 0.0254 (9) | 0.0237 (9) | −0.0103 (7) | 0.0033 (6) | −0.0123 (7) |
C10 | 0.0155 (7) | 0.0146 (8) | 0.0173 (8) | −0.0077 (6) | 0.0012 (5) | −0.0051 (6) |
C11 | 0.0216 (8) | 0.0188 (8) | 0.0166 (8) | −0.0087 (6) | 0.0035 (6) | −0.0036 (7) |
C12 | 0.0219 (8) | 0.0173 (8) | 0.0238 (9) | −0.0074 (6) | 0.0002 (6) | −0.0019 (7) |
C13 | 0.0179 (8) | 0.0182 (8) | 0.0311 (9) | −0.0058 (6) | 0.0027 (7) | −0.0103 (7) |
C14 | 0.0222 (8) | 0.0260 (9) | 0.0221 (9) | −0.0085 (7) | 0.0054 (6) | −0.0119 (7) |
C15 | 0.0217 (8) | 0.0203 (8) | 0.0154 (8) | −0.0069 (6) | 0.0010 (6) | −0.0055 (7) |
C16 | 0.0204 (8) | 0.0153 (8) | 0.0182 (8) | −0.0077 (6) | 0.0027 (6) | −0.0014 (6) |
C17 | 0.0224 (8) | 0.0157 (8) | 0.0176 (8) | −0.0064 (6) | 0.0032 (6) | −0.0073 (6) |
C18 | 0.0218 (8) | 0.0188 (9) | 0.0272 (9) | −0.0006 (7) | −0.0012 (7) | −0.0077 (7) |
C19 | 0.0322 (10) | 0.0221 (9) | 0.0264 (10) | −0.0013 (8) | −0.0018 (8) | −0.0047 (8) |
O1—C1 | 1.2088 (17) | C8—H8 | 0.943 (19) |
O2—C2 | 1.2307 (18) | C9—H9 | 0.978 (18) |
O3—C17 | 1.2025 (19) | C10—C15 | 1.389 (2) |
O4—C17 | 1.3325 (19) | C10—C11 | 1.396 (2) |
O4—C18 | 1.4681 (19) | C11—C12 | 1.386 (2) |
N1—C2 | 1.3378 (19) | C11—H11 | 0.975 (18) |
N1—C3 | 1.4687 (18) | C12—C13 | 1.389 (2) |
N1—H1 | 0.91 (2) | C12—H12 | 0.996 (18) |
N2—C1 | 1.3760 (19) | C13—C14 | 1.383 (2) |
N2—C2 | 1.4005 (19) | C13—H13 | 0.978 (18) |
N2—C16 | 1.4433 (19) | C14—C15 | 1.392 (2) |
C1—C3 | 1.543 (2) | C14—H14 | 0.973 (19) |
C3—C10 | 1.533 (2) | C15—H15 | 0.954 (18) |
C3—C4 | 1.533 (2) | C16—C17 | 1.515 (2) |
C4—C9 | 1.387 (2) | C16—H16A | 0.971 (18) |
C4—C5 | 1.395 (2) | C16—H16B | 0.958 (18) |
C5—C6 | 1.392 (2) | C18—C19 | 1.497 (3) |
C5—H5 | 0.989 (18) | C18—H18A | 0.977 (18) |
C6—C7 | 1.383 (2) | C18—H18B | 0.968 (19) |
C6—H6 | 0.985 (19) | C19—H19A | 1.03 (2) |
C7—C8 | 1.381 (3) | C19—H19B | 1.02 (2) |
C7—H7 | 1.01 (2) | C19—H19C | 0.99 (2) |
C8—C9 | 1.393 (2) | ||
C17—O4—C18 | 116.34 (13) | C15—C10—C3 | 122.84 (13) |
C2—N1—C3 | 113.27 (13) | C11—C10—C3 | 118.04 (14) |
C2—N1—H1 | 122.0 (12) | C12—C11—C10 | 120.65 (15) |
C3—N1—H1 | 124.3 (12) | C12—C11—H11 | 120.4 (10) |
C1—N2—C2 | 111.55 (12) | C10—C11—H11 | 118.9 (10) |
C1—N2—C16 | 124.09 (13) | C11—C12—C13 | 120.01 (15) |
C2—N2—C16 | 123.48 (13) | C11—C12—H12 | 120.1 (10) |
O1—C1—N2 | 125.56 (14) | C13—C12—H12 | 119.8 (10) |
O1—C1—C3 | 127.87 (14) | C14—C13—C12 | 119.56 (16) |
N2—C1—C3 | 106.56 (12) | C14—C13—H13 | 120.5 (10) |
O2—C2—N1 | 128.79 (14) | C12—C13—H13 | 120.0 (10) |
O2—C2—N2 | 123.61 (14) | C13—C14—C15 | 120.65 (16) |
N1—C2—N2 | 107.59 (13) | C13—C14—H14 | 120.7 (11) |
N1—C3—C10 | 109.98 (11) | C15—C14—H14 | 118.6 (11) |
N1—C3—C4 | 110.84 (12) | C10—C15—C14 | 120.00 (15) |
C10—C3—C4 | 113.22 (12) | C10—C15—H15 | 120.4 (11) |
N1—C3—C1 | 100.42 (11) | C14—C15—H15 | 119.6 (11) |
C10—C3—C1 | 111.28 (12) | N2—C16—C17 | 111.31 (13) |
C4—C3—C1 | 110.38 (12) | N2—C16—H16A | 109.3 (11) |
C9—C4—C5 | 119.09 (14) | C17—C16—H16A | 109.1 (10) |
C9—C4—C3 | 121.76 (14) | N2—C16—H16B | 107.2 (11) |
C5—C4—C3 | 119.15 (13) | C17—C16—H16B | 110.0 (11) |
C6—C5—C4 | 120.39 (16) | H16A—C16—H16B | 109.8 (15) |
C6—C5—H5 | 121.0 (11) | O3—C17—O4 | 125.56 (15) |
C4—C5—H5 | 118.6 (11) | O3—C17—C16 | 125.00 (15) |
C7—C6—C5 | 120.01 (17) | O4—C17—C16 | 109.44 (13) |
C7—C6—H6 | 121.3 (11) | O4—C18—C19 | 106.36 (15) |
C5—C6—H6 | 118.7 (11) | O4—C18—H18A | 108.3 (11) |
C8—C7—C6 | 119.93 (16) | C19—C18—H18A | 112.0 (11) |
C8—C7—H7 | 119.3 (11) | O4—C18—H18B | 108.4 (11) |
C6—C7—H7 | 120.8 (11) | C19—C18—H18B | 112.7 (10) |
C7—C8—C9 | 120.29 (17) | H18A—C18—H18B | 108.9 (15) |
C7—C8—H8 | 121.1 (12) | C18—C19—H19A | 109.9 (11) |
C9—C8—H8 | 118.6 (12) | C18—C19—H19B | 112.2 (11) |
C4—C9—C8 | 120.27 (16) | H19A—C19—H19B | 108.1 (16) |
C4—C9—H9 | 119.2 (10) | C18—C19—H19C | 111.1 (12) |
C8—C9—H9 | 120.5 (10) | H19A—C19—H19C | 109.3 (16) |
C15—C10—C11 | 119.11 (14) | H19B—C19—H19C | 106.1 (17) |
C2—N2—C1—O1 | −172.06 (14) | C4—C5—C6—C7 | 0.1 (2) |
C16—N2—C1—O1 | −2.5 (2) | C5—C6—C7—C8 | 0.8 (3) |
C2—N2—C1—C3 | 8.07 (16) | C6—C7—C8—C9 | −0.5 (3) |
C16—N2—C1—C3 | 177.66 (13) | C5—C4—C9—C8 | 1.4 (2) |
C3—N1—C2—O2 | −178.70 (15) | C3—C4—C9—C8 | −178.82 (14) |
C3—N1—C2—N2 | 1.34 (17) | C7—C8—C9—C4 | −0.6 (3) |
C1—N2—C2—O2 | 173.90 (14) | N1—C3—C10—C15 | 126.47 (15) |
C16—N2—C2—O2 | 4.2 (2) | C4—C3—C10—C15 | −108.93 (16) |
C1—N2—C2—N1 | −6.13 (17) | C1—C3—C10—C15 | 16.09 (19) |
C16—N2—C2—N1 | −175.80 (13) | N1—C3—C10—C11 | −52.87 (17) |
C2—N1—C3—C10 | −114.14 (14) | C4—C3—C10—C11 | 71.73 (17) |
C2—N1—C3—C4 | 119.90 (14) | C1—C3—C10—C11 | −163.25 (13) |
C2—N1—C3—C1 | 3.23 (16) | C15—C10—C11—C12 | 1.1 (2) |
O1—C1—C3—N1 | 173.53 (15) | C3—C10—C11—C12 | −179.49 (13) |
N2—C1—C3—N1 | −6.61 (14) | C10—C11—C12—C13 | −1.3 (2) |
O1—C1—C3—C10 | −70.07 (19) | C11—C12—C13—C14 | 0.3 (2) |
N2—C1—C3—C10 | 109.79 (13) | C12—C13—C14—C15 | 0.9 (2) |
O1—C1—C3—C4 | 56.5 (2) | C11—C10—C15—C14 | 0.1 (2) |
N2—C1—C3—C4 | −123.62 (13) | C3—C10—C15—C14 | −179.25 (14) |
N1—C3—C4—C9 | 138.84 (14) | C13—C14—C15—C10 | −1.1 (2) |
C10—C3—C4—C9 | 14.70 (19) | C1—N2—C16—C17 | −70.75 (19) |
C1—C3—C4—C9 | −110.80 (16) | C2—N2—C16—C17 | 97.63 (17) |
N1—C3—C4—C5 | −41.42 (18) | C18—O4—C17—O3 | 2.5 (2) |
C10—C3—C4—C5 | −165.55 (13) | C18—O4—C17—C16 | −176.91 (13) |
C1—C3—C4—C5 | 68.94 (17) | N2—C16—C17—O3 | −4.4 (2) |
C9—C4—C5—C6 | −1.2 (2) | N2—C16—C17—O4 | 174.99 (12) |
C3—C4—C5—C6 | 179.04 (14) | C17—O4—C18—C19 | −176.90 (14) |
Cg2 and Cg3 are the centroids of the C4–C9 and C10–C15 benzene rings, respectively, |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.91 (2) | 1.91 (2) | 2.8203 (17) | 172.6 (17) |
C15—H15···O1ii | 0.954 (18) | 2.591 (18) | 3.332 (2) | 134.8 (14) |
C16—H16A···O4iii | 0.971 (18) | 2.653 (19) | 3.415 (2) | 135.7 (13) |
C18—H18A···O3iv | 0.977 (18) | 2.658 (19) | 3.633 (2) | 175.9 (14) |
C7—H7···Cg3v | 1.01 (2) | 2.976 (18) | 3.6661 (19) | 126.6 (13) |
C12—H12···Cg2vi | 0.996 (18) | 2.701 (18) | 3.6673 (19) | 163.1 (18) |
C19—H19A···Cg2 | 1.03 (2) | 2.83 (2) | 3.572 (2) | 129.0 (16) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y, −z+1; (v) x+1, y, z; (vi) −x+1, −y+2, −z. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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