organic compounds
[(1R*,3S*,4S*)-3-(2-Hydroxybenzoyl)-1,2,3,4-tetrahydro-1,4-epoxynaphthalen-1-yl]methyl 4-nitrobenzoate
aDepartment of Chemistry, University of Toronto, Toronto, Ontario, M5S 3H6, Canada, and bDepartment of Chemistry, University of Guelph, Guelph, Ontario, N1G 2W1, Canada
*Correspondence e-mail: alan.lough@utoronto.ca
The relative stereo- and regiochemistry of the racemic title compound, C25H19NO7, were established from the The fused benzene ring forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hydroxy-substituted benzene ring and the nitro-substituted benzene ring, respectively. The dihedral angle between the hydroxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intramolecular O—H⋯O hydrogen bond closes an S(6) ring. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules, forming layers parallel to (100). Within these layers, there are weak π–π stacking interactions with a ring centroid–ring centroid distance of 3.555 (1) Å.
Keywords: crystal structure; regioselectivity; weak hydrogen bonding.
CCDC reference: 1986297
Structure description
In past years, our research group (Ballantine et al., 2009; Edmunds et al., 2015; Hill & Tam, 2019; Edmunds et al., 2016; Raheem et al., 2014) has investigated the effects of various C1-substituted oxabenzonorbornadienes (OBD) on controlling the regioselectivity of ring-opening reactions. In 2015, Nagamoto and Nishimura reported the iridium-catalysed hydroacylation reaction of bicyclic with 2-hydroxybenzaldehyde and its derivatives. Based upon these findings, we set out to determine the effect of C1 substitution on controlling the regioselectivity in the iridium-catalysed hydroacylation reaction with salicylaldehyde II (see Fig. 1) on unsymmetrical oxabenzonorbornadienes. Reaction of C1-substituted OBD (I) with salicylaldehyde II in the presence of [Ir(COD)Cl]2 (COD = 1,5-cyclooctaiene), and 5 M KOH afforded exclusively the title C3 regioisomer (III) in a 82% yield. The relative stereo- and regiochemistry of the adduct system was determined by single-crystal X-ray analysis. There are two possible as the addition can occur on the exo or the endo face, and two possible regioisomers as the addition can occur at the C2 or C3 position. Of the four possible stereo- and regio-isomers, only the exo-C3 isomer was obtained. The title compound is racemic: in the arbitrarily chosen the stereogenic centres are as follows: C1 R; C3 S; C4 S.
The molecular structure of the title compound is shown in Fig. 2. The fused benzene ring (C5–C10) forms dihedral angles of 77.3 (1) and 60.3 (1)° with the hydroxy-substituted benzene ring (C12–C17) and the nitro-substituted benzene ring (C20–C25), respectively. The dihedral angle between the hydroxy-substituted benzene ring and the nitro-substituted benzene ring is 76.4 (1)°. An intramolecular O—H⋯O hydrogen bond is observed. In the crystal, weak C—H⋯O hydrogen bonds (Table 1) connect the molecules, forming layers lying parallel to (100) (Fig. 3). Within these layers, there are weak π–π stacking interactions with a ring centroid–ring centroid distance of 3.555 (1) Å for Cg⋯Cg(1 − x, −y, 1 − z) where Cg is the centroid of the C20–C25 ring.
Synthesis and crystallization
To a dried screw-cap vial, was added [Ir(COD)Cl]2 (10 mg, 5 mol%), C1-substituted oxabenzonorbornadiene (I) (Fig. 1) (0.3 mmol, 1.2 equiv.), salicylaldehyde II (27 µl, 1 equiv.) and 5M KOH (0.03 mmol, 10 mol%) dissolved in 2 ml of 1,4-dioxane. The reaction was left to stir at 338 K for 20 h, the resultant mixture was loaded directly onto a column and the crude reaction mixture was purified by flash (EtOAc:hexanes 25:75) to obtain the adduct product III (101 mg, 0.23 mmol, 82%) as a yellow solid. The product was then subsequently recrystallized from solution in pure hexanes by slow evaporation of the solvent to give product III as colourless crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1986297
https://doi.org/10.1107/S2414314620002655/hb4338sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620002655/hb4338Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620002655/hb4338Isup3.cml
Data collection: APEX3 (Bruker, 2019); cell
APEX3 (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: PLATON (Spek, 2020); software used to prepare material for publication: publCIF (Westrip, 2010).C25H19NO7 | F(000) = 928 |
Mr = 445.41 | Dx = 1.434 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.7455 (10) Å | Cell parameters from 9213 reflections |
b = 11.9504 (8) Å | θ = 2.4–27.2° |
c = 11.9649 (8) Å | µ = 0.11 mm−1 |
β = 101.898 (2)° | T = 150 K |
V = 2063.1 (2) Å3 | Shard, colourless |
Z = 4 | 0.32 × 0.30 × 0.16 mm |
Bruker Kappa APEX DUO PHOTON II diffractometer | 3399 reflections with I > 2σ(I) |
Radiation source: sealed tube with Bruker Triumph monochromator | Rint = 0.059 |
φ and ω scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan (Krause et al., 2015) | h = −19→19 |
Tmin = 0.623, Tmax = 0.746 | k = −15→15 |
40054 measured reflections | l = −15→15 |
4727 independent reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.5845P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4727 reflections | Δρmax = 0.25 e Å−3 |
302 parameters | Δρmin = −0.21 e Å−3 |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.21520 (6) | 0.45410 (8) | 0.52221 (8) | 0.0254 (2) | |
O2 | 0.09918 (8) | 0.66077 (8) | 0.55530 (9) | 0.0357 (3) | |
O3 | 0.08195 (8) | 0.86474 (10) | 0.60434 (9) | 0.0376 (3) | |
H3O | 0.0802 (14) | 0.7862 (18) | 0.6067 (18) | 0.069 (6)* | |
O4 | 0.37771 (6) | 0.32000 (8) | 0.53811 (9) | 0.0295 (2) | |
O5 | 0.53204 (7) | 0.32594 (9) | 0.60060 (9) | 0.0336 (2) | |
O6 | 0.35631 (8) | −0.23766 (9) | 0.63820 (10) | 0.0430 (3) | |
O7 | 0.50514 (8) | −0.25121 (9) | 0.65612 (9) | 0.0393 (3) | |
N1 | 0.43308 (9) | −0.19667 (10) | 0.64302 (10) | 0.0317 (3) | |
C1 | 0.27856 (9) | 0.46052 (11) | 0.44429 (11) | 0.0239 (3) | |
C2 | 0.26049 (9) | 0.58196 (11) | 0.39894 (12) | 0.0247 (3) | |
H2A | 0.275088 | 0.590603 | 0.322264 | 0.030* | |
H2B | 0.296733 | 0.637046 | 0.451839 | 0.030* | |
C3 | 0.15431 (9) | 0.59376 (11) | 0.39449 (11) | 0.0238 (3) | |
H3A | 0.120016 | 0.605331 | 0.314073 | 0.029* | |
C4 | 0.13143 (9) | 0.47745 (11) | 0.43864 (12) | 0.0249 (3) | |
H4A | 0.072919 | 0.474098 | 0.468439 | 0.030* | |
C5 | 0.13776 (9) | 0.39344 (11) | 0.34635 (12) | 0.0249 (3) | |
C6 | 0.07283 (10) | 0.33873 (12) | 0.26533 (13) | 0.0302 (3) | |
H6A | 0.008319 | 0.348599 | 0.261361 | 0.036* | |
C7 | 0.10549 (11) | 0.26840 (12) | 0.18949 (13) | 0.0332 (3) | |
H7A | 0.062396 | 0.228731 | 0.133444 | 0.040* | |
C8 | 0.19923 (11) | 0.25522 (12) | 0.19418 (12) | 0.0319 (3) | |
H8A | 0.219548 | 0.206293 | 0.141757 | 0.038* | |
C9 | 0.26456 (10) | 0.31274 (11) | 0.27481 (12) | 0.0283 (3) | |
H9A | 0.329065 | 0.304773 | 0.277455 | 0.034* | |
C10 | 0.23228 (9) | 0.38140 (11) | 0.35039 (11) | 0.0235 (3) | |
C11 | 0.13163 (9) | 0.68588 (11) | 0.47082 (11) | 0.0254 (3) | |
C12 | 0.14368 (9) | 0.80400 (11) | 0.44234 (12) | 0.0250 (3) | |
C13 | 0.11508 (10) | 0.88844 (12) | 0.50972 (12) | 0.0283 (3) | |
C14 | 0.11990 (10) | 1.00024 (12) | 0.47954 (14) | 0.0349 (4) | |
H14A | 0.100414 | 1.056998 | 0.524970 | 0.042* | |
C15 | 0.15290 (11) | 1.02872 (12) | 0.38389 (14) | 0.0369 (4) | |
H15A | 0.155158 | 1.105273 | 0.363255 | 0.044* | |
C16 | 0.18300 (10) | 0.94724 (12) | 0.31691 (13) | 0.0340 (3) | |
H16A | 0.206590 | 0.967947 | 0.251714 | 0.041* | |
C17 | 0.17825 (10) | 0.83600 (12) | 0.34613 (12) | 0.0287 (3) | |
H17A | 0.198678 | 0.780174 | 0.300444 | 0.034* | |
C18 | 0.37610 (10) | 0.43650 (11) | 0.50427 (12) | 0.0279 (3) | |
H18A | 0.419456 | 0.449528 | 0.452497 | 0.034* | |
H18B | 0.394223 | 0.485260 | 0.572100 | 0.034* | |
C19 | 0.46027 (9) | 0.27418 (12) | 0.57989 (11) | 0.0253 (3) | |
C20 | 0.45169 (9) | 0.15105 (11) | 0.59774 (11) | 0.0247 (3) | |
C21 | 0.36672 (9) | 0.09770 (12) | 0.56869 (12) | 0.0274 (3) | |
H21A | 0.312763 | 0.139404 | 0.536667 | 0.033* | |
C22 | 0.36020 (10) | −0.01641 (12) | 0.58624 (12) | 0.0287 (3) | |
H22A | 0.302095 | −0.053641 | 0.568005 | 0.034* | |
C23 | 0.44020 (10) | −0.07438 (12) | 0.63079 (11) | 0.0273 (3) | |
C24 | 0.52603 (10) | −0.02386 (12) | 0.65983 (12) | 0.0293 (3) | |
H24A | 0.579934 | −0.066435 | 0.689955 | 0.035* | |
C25 | 0.53146 (10) | 0.09052 (12) | 0.64388 (12) | 0.0284 (3) | |
H25A | 0.589463 | 0.127695 | 0.664342 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0287 (5) | 0.0252 (5) | 0.0235 (5) | 0.0008 (4) | 0.0085 (4) | 0.0022 (4) |
O2 | 0.0536 (7) | 0.0288 (5) | 0.0292 (5) | 0.0063 (5) | 0.0189 (5) | 0.0028 (4) |
O3 | 0.0493 (7) | 0.0330 (6) | 0.0332 (6) | 0.0069 (5) | 0.0145 (5) | −0.0052 (5) |
O4 | 0.0247 (5) | 0.0248 (5) | 0.0380 (6) | 0.0019 (4) | 0.0040 (4) | 0.0041 (4) |
O5 | 0.0259 (5) | 0.0370 (6) | 0.0358 (6) | −0.0032 (5) | 0.0019 (4) | 0.0034 (5) |
O6 | 0.0423 (7) | 0.0330 (6) | 0.0484 (7) | −0.0031 (5) | −0.0029 (5) | 0.0024 (5) |
O7 | 0.0485 (7) | 0.0354 (6) | 0.0344 (6) | 0.0168 (5) | 0.0097 (5) | 0.0035 (5) |
N1 | 0.0408 (8) | 0.0302 (7) | 0.0224 (6) | 0.0058 (6) | 0.0027 (5) | −0.0004 (5) |
C1 | 0.0258 (7) | 0.0230 (7) | 0.0245 (7) | −0.0012 (5) | 0.0085 (6) | 0.0011 (5) |
C2 | 0.0277 (7) | 0.0212 (6) | 0.0260 (7) | −0.0009 (5) | 0.0074 (6) | 0.0007 (5) |
C3 | 0.0272 (7) | 0.0219 (7) | 0.0228 (7) | 0.0008 (5) | 0.0059 (5) | 0.0002 (5) |
C4 | 0.0236 (7) | 0.0241 (7) | 0.0278 (7) | 0.0015 (5) | 0.0072 (6) | 0.0017 (6) |
C5 | 0.0278 (7) | 0.0193 (6) | 0.0280 (7) | −0.0008 (5) | 0.0069 (6) | 0.0025 (5) |
C6 | 0.0279 (7) | 0.0254 (7) | 0.0360 (8) | −0.0022 (6) | 0.0036 (6) | 0.0018 (6) |
C7 | 0.0402 (9) | 0.0258 (7) | 0.0307 (8) | −0.0053 (6) | 0.0007 (7) | −0.0019 (6) |
C8 | 0.0441 (9) | 0.0242 (7) | 0.0284 (7) | 0.0012 (6) | 0.0098 (7) | −0.0032 (6) |
C9 | 0.0311 (8) | 0.0251 (7) | 0.0305 (8) | 0.0010 (6) | 0.0105 (6) | 0.0011 (6) |
C10 | 0.0265 (7) | 0.0202 (6) | 0.0242 (7) | −0.0012 (5) | 0.0058 (5) | 0.0031 (5) |
C11 | 0.0273 (7) | 0.0263 (7) | 0.0220 (7) | 0.0039 (6) | 0.0036 (6) | 0.0020 (6) |
C12 | 0.0250 (7) | 0.0240 (7) | 0.0239 (7) | 0.0026 (5) | 0.0003 (5) | 0.0000 (5) |
C13 | 0.0268 (7) | 0.0280 (7) | 0.0279 (7) | 0.0035 (6) | 0.0010 (6) | −0.0021 (6) |
C14 | 0.0317 (8) | 0.0259 (7) | 0.0440 (9) | 0.0040 (6) | 0.0005 (7) | −0.0062 (7) |
C15 | 0.0372 (9) | 0.0223 (7) | 0.0460 (9) | 0.0010 (6) | −0.0032 (7) | 0.0046 (7) |
C16 | 0.0354 (8) | 0.0305 (8) | 0.0338 (8) | −0.0035 (6) | 0.0015 (7) | 0.0066 (6) |
C17 | 0.0307 (7) | 0.0267 (7) | 0.0269 (7) | −0.0006 (6) | 0.0018 (6) | 0.0006 (6) |
C18 | 0.0282 (7) | 0.0227 (7) | 0.0322 (8) | −0.0011 (6) | 0.0044 (6) | 0.0022 (6) |
C19 | 0.0237 (7) | 0.0326 (8) | 0.0197 (7) | 0.0025 (6) | 0.0049 (5) | −0.0008 (6) |
C20 | 0.0265 (7) | 0.0281 (7) | 0.0200 (6) | 0.0027 (6) | 0.0060 (5) | −0.0010 (5) |
C21 | 0.0244 (7) | 0.0293 (7) | 0.0286 (7) | 0.0057 (6) | 0.0053 (6) | −0.0008 (6) |
C22 | 0.0269 (7) | 0.0287 (7) | 0.0305 (7) | 0.0004 (6) | 0.0058 (6) | −0.0025 (6) |
C23 | 0.0336 (8) | 0.0277 (7) | 0.0208 (7) | 0.0061 (6) | 0.0062 (6) | −0.0002 (5) |
C24 | 0.0289 (8) | 0.0335 (8) | 0.0243 (7) | 0.0090 (6) | 0.0030 (6) | 0.0004 (6) |
C25 | 0.0248 (7) | 0.0344 (8) | 0.0251 (7) | 0.0023 (6) | 0.0035 (6) | −0.0018 (6) |
O1—C4 | 1.4471 (16) | C8—C9 | 1.396 (2) |
O1—C1 | 1.4515 (15) | C8—H8A | 0.9500 |
O2—C11 | 1.2410 (16) | C9—C10 | 1.3766 (19) |
O3—C13 | 1.3523 (18) | C9—H9A | 0.9500 |
O3—H3O | 0.94 (2) | C11—C12 | 1.4715 (19) |
O4—C19 | 1.3345 (16) | C12—C17 | 1.405 (2) |
O4—C18 | 1.4487 (16) | C12—C13 | 1.4093 (19) |
O5—C19 | 1.2066 (16) | C13—C14 | 1.390 (2) |
O6—N1 | 1.2238 (16) | C14—C15 | 1.375 (2) |
O7—N1 | 1.2287 (15) | C14—H14A | 0.9500 |
N1—C23 | 1.4746 (19) | C15—C16 | 1.391 (2) |
C1—C18 | 1.4968 (19) | C15—H15A | 0.9500 |
C1—C10 | 1.5185 (18) | C16—C17 | 1.380 (2) |
C1—C2 | 1.5531 (18) | C16—H16A | 0.9500 |
C2—C3 | 1.5620 (19) | C17—H17A | 0.9500 |
C2—H2A | 0.9900 | C18—H18A | 0.9900 |
C2—H2B | 0.9900 | C18—H18B | 0.9900 |
C3—C11 | 1.5112 (18) | C19—C20 | 1.4959 (19) |
C3—C4 | 1.5486 (18) | C20—C21 | 1.3848 (19) |
C3—H3A | 1.0000 | C20—C25 | 1.3942 (19) |
C4—C5 | 1.5095 (19) | C21—C22 | 1.386 (2) |
C4—H4A | 1.0000 | C21—H21A | 0.9500 |
C5—C6 | 1.3788 (19) | C22—C23 | 1.3770 (19) |
C5—C10 | 1.3920 (19) | C22—H22A | 0.9500 |
C6—C7 | 1.393 (2) | C23—C24 | 1.380 (2) |
C6—H6A | 0.9500 | C24—C25 | 1.385 (2) |
C7—C8 | 1.381 (2) | C24—H24A | 0.9500 |
C7—H7A | 0.9500 | C25—H25A | 0.9500 |
C4—O1—C1 | 96.71 (9) | O2—C11—C12 | 120.38 (12) |
C13—O3—H3O | 104.6 (13) | O2—C11—C3 | 119.12 (12) |
C19—O4—C18 | 117.40 (11) | C12—C11—C3 | 120.43 (12) |
O6—N1—O7 | 124.11 (13) | C17—C12—C13 | 118.41 (13) |
O6—N1—C23 | 118.42 (12) | C17—C12—C11 | 122.17 (12) |
O7—N1—C23 | 117.46 (13) | C13—C12—C11 | 119.33 (13) |
O1—C1—C18 | 111.35 (11) | O3—C13—C14 | 117.75 (13) |
O1—C1—C10 | 101.05 (10) | O3—C13—C12 | 122.09 (13) |
C18—C1—C10 | 118.44 (11) | C14—C13—C12 | 120.16 (14) |
O1—C1—C2 | 100.78 (10) | C15—C14—C13 | 119.99 (14) |
C18—C1—C2 | 115.17 (11) | C15—C14—H14A | 120.0 |
C10—C1—C2 | 107.74 (11) | C13—C14—H14A | 120.0 |
C1—C2—C3 | 101.24 (10) | C14—C15—C16 | 121.06 (14) |
C1—C2—H2A | 111.5 | C14—C15—H15A | 119.5 |
C3—C2—H2A | 111.5 | C16—C15—H15A | 119.5 |
C1—C2—H2B | 111.5 | C17—C16—C15 | 119.31 (15) |
C3—C2—H2B | 111.5 | C17—C16—H16A | 120.3 |
H2A—C2—H2B | 109.3 | C15—C16—H16A | 120.3 |
C11—C3—C4 | 110.90 (11) | C16—C17—C12 | 121.05 (14) |
C11—C3—C2 | 112.98 (11) | C16—C17—H17A | 119.5 |
C4—C3—C2 | 101.22 (10) | C12—C17—H17A | 119.5 |
C11—C3—H3A | 110.5 | O4—C18—C1 | 106.08 (11) |
C4—C3—H3A | 110.5 | O4—C18—H18A | 110.5 |
C2—C3—H3A | 110.5 | C1—C18—H18A | 110.5 |
O1—C4—C5 | 101.80 (10) | O4—C18—H18B | 110.5 |
O1—C4—C3 | 101.18 (10) | C1—C18—H18B | 110.5 |
C5—C4—C3 | 107.26 (11) | H18A—C18—H18B | 108.7 |
O1—C4—H4A | 115.0 | O5—C19—O4 | 124.08 (13) |
C5—C4—H4A | 115.0 | O5—C19—C20 | 124.85 (12) |
C3—C4—H4A | 115.0 | O4—C19—C20 | 111.08 (11) |
C6—C5—C10 | 121.37 (13) | C21—C20—C25 | 120.42 (13) |
C6—C5—C4 | 133.71 (13) | C21—C20—C19 | 121.05 (12) |
C10—C5—C4 | 104.82 (11) | C25—C20—C19 | 118.53 (12) |
C5—C6—C7 | 117.43 (13) | C20—C21—C22 | 120.16 (13) |
C5—C6—H6A | 121.3 | C20—C21—H21A | 119.9 |
C7—C6—H6A | 121.3 | C22—C21—H21A | 119.9 |
C8—C7—C6 | 121.32 (14) | C23—C22—C21 | 118.22 (13) |
C8—C7—H7A | 119.3 | C23—C22—H22A | 120.9 |
C6—C7—H7A | 119.3 | C21—C22—H22A | 120.9 |
C7—C8—C9 | 120.95 (13) | C22—C23—C24 | 123.04 (14) |
C7—C8—H8A | 119.5 | C22—C23—N1 | 117.66 (13) |
C9—C8—H8A | 119.5 | C24—C23—N1 | 119.26 (12) |
C10—C9—C8 | 117.70 (13) | C23—C24—C25 | 118.24 (13) |
C10—C9—H9A | 121.2 | C23—C24—H24A | 120.9 |
C8—C9—H9A | 121.2 | C25—C24—H24A | 120.9 |
C9—C10—C5 | 121.20 (13) | C24—C25—C20 | 119.91 (13) |
C9—C10—C1 | 133.92 (12) | C24—C25—H25A | 120.0 |
C5—C10—C1 | 104.80 (11) | C20—C25—H25A | 120.0 |
C4—O1—C1—C18 | −178.46 (11) | O2—C11—C12—C17 | −178.58 (13) |
C4—O1—C1—C10 | −51.79 (11) | C3—C11—C12—C17 | −1.5 (2) |
C4—O1—C1—C2 | 58.90 (11) | O2—C11—C12—C13 | −2.1 (2) |
O1—C1—C2—C3 | −35.63 (12) | C3—C11—C12—C13 | 174.94 (12) |
C18—C1—C2—C3 | −155.56 (11) | C17—C12—C13—O3 | −179.28 (12) |
C10—C1—C2—C3 | 69.79 (12) | C11—C12—C13—O3 | 4.1 (2) |
C1—C2—C3—C11 | 118.93 (12) | C17—C12—C13—C14 | 1.1 (2) |
C1—C2—C3—C4 | 0.30 (12) | C11—C12—C13—C14 | −175.51 (13) |
C1—O1—C4—C5 | 51.61 (11) | O3—C13—C14—C15 | −179.85 (13) |
C1—O1—C4—C3 | −58.89 (11) | C12—C13—C14—C15 | −0.2 (2) |
C11—C3—C4—O1 | −84.83 (12) | C13—C14—C15—C16 | −0.9 (2) |
C2—C3—C4—O1 | 35.28 (12) | C14—C15—C16—C17 | 1.0 (2) |
C11—C3—C4—C5 | 168.93 (11) | C15—C16—C17—C12 | −0.1 (2) |
C2—C3—C4—C5 | −70.96 (12) | C13—C12—C17—C16 | −0.9 (2) |
O1—C4—C5—C6 | 151.71 (15) | C11—C12—C17—C16 | 175.55 (13) |
C3—C4—C5—C6 | −102.49 (17) | C19—O4—C18—C1 | 171.18 (11) |
O1—C4—C5—C10 | −32.04 (13) | O1—C1—C18—O4 | 66.60 (13) |
C3—C4—C5—C10 | 73.76 (13) | C10—C1—C18—O4 | −49.87 (15) |
C10—C5—C6—C7 | 1.7 (2) | C2—C1—C18—O4 | −179.47 (11) |
C4—C5—C6—C7 | 177.47 (14) | C18—O4—C19—O5 | 6.95 (19) |
C5—C6—C7—C8 | −0.9 (2) | C18—O4—C19—C20 | −173.23 (11) |
C6—C7—C8—C9 | −0.5 (2) | O5—C19—C20—C21 | −178.22 (13) |
C7—C8—C9—C10 | 1.0 (2) | O4—C19—C20—C21 | 1.96 (18) |
C8—C9—C10—C5 | −0.2 (2) | O5—C19—C20—C25 | 1.4 (2) |
C8—C9—C10—C1 | −176.44 (14) | O4—C19—C20—C25 | −178.39 (11) |
C6—C5—C10—C9 | −1.2 (2) | C25—C20—C21—C22 | 0.6 (2) |
C4—C5—C10—C9 | −178.00 (12) | C19—C20—C21—C22 | −179.80 (13) |
C6—C5—C10—C1 | 176.00 (12) | C20—C21—C22—C23 | −1.2 (2) |
C4—C5—C10—C1 | −0.82 (13) | C21—C22—C23—C24 | 0.8 (2) |
O1—C1—C10—C9 | −150.10 (15) | C21—C22—C23—N1 | −176.67 (12) |
C18—C1—C10—C9 | −28.3 (2) | O6—N1—C23—C22 | −16.19 (19) |
C2—C1—C10—C9 | 104.67 (17) | O7—N1—C23—C22 | 162.95 (12) |
O1—C1—C10—C5 | 33.25 (12) | O6—N1—C23—C24 | 166.29 (13) |
C18—C1—C10—C5 | 155.09 (12) | O7—N1—C23—C24 | −14.57 (18) |
C2—C1—C10—C5 | −71.98 (13) | C22—C23—C24—C25 | 0.4 (2) |
C4—C3—C11—O2 | −0.02 (17) | N1—C23—C24—C25 | 177.78 (12) |
C2—C3—C11—O2 | −112.86 (14) | C23—C24—C25—C20 | −1.1 (2) |
C4—C3—C11—C12 | −177.14 (12) | C21—C20—C25—C24 | 0.6 (2) |
C2—C3—C11—C12 | 70.02 (15) | C19—C20—C25—C24 | −179.03 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3O···O2 | 0.94 (2) | 1.67 (2) | 2.5321 (15) | 151.7 (19) |
C3—H3A···O3i | 1.00 | 2.48 | 3.4510 (17) | 163 |
C8—H8A···O1ii | 0.95 | 2.38 | 3.2782 (17) | 157 |
C9—H9A···O7iii | 0.95 | 2.49 | 3.4057 (19) | 161 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+1/2, z−1/2; (iii) −x+1, −y, −z+1. |
Acknowledgements
The University of Toronto thanks NSERC Canada for funding.
References
Ballantine, M., Menard, M. L. & Tam, W. (2009). J. Org. Chem. 74, 7570–7573. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2019). APEX3 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Edmunds, M., Menard, M. L. & Tam, W. (2015). Synth. Commun. 45, 458–466. Web of Science CrossRef CAS Google Scholar
Edmunds, M., Raheem, M.-A., Boutin, R., Tait, K. & Tam, W. (2016). Beilstein J. Org. Chem. 12, 239–244. Web of Science CrossRef CAS PubMed Google Scholar
Hill, J. & Tam, W. (2019). J. Org. Chem. 84, 8309–8314. CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Nagamoto, M. & Nishimura, T. (2015). Chem. Commun. 51, 13791–13794. CrossRef CAS Google Scholar
Raheem, M. A., Edmunds, M. & Tam, W. (2014). Can. J. Chem. 92, 888–895. CrossRef CAS Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.