research communications
Synthesis, E)-benzo[d][1,3]dioxole-5-carbaldehyde oxime
and Hirshfeld surface analysis of (aP. G. & Research Department of Physics, Jamal Mohamed College (Autonomous), (affiliated to Bharathidasan University), Tiruchirappalli 620 020, Tamilnadu, India, bLaboratoire Chimie Organique Catalyse et Environnement, Faculté des Sciences, Kenitra, Morocco, cLaboratory of Chemistry and Environment, Applied Bioorganic Chemistry Team, Faculty of Sciences, Ibn Zohr University, Agadir, Morocco, dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ePrincipal (Retired), Kunthavai Naacchiyaar Government Arts College for Women (Autonomous), Thanjavur 613 007, Tamilnadu, India
*Correspondence e-mail: thiruvalluvar.a@gmail.com
The 8H7NO3, consists of two molecules differing slightly in conformation and in their intermolecular interactions in the solid. The dihedral angle between the benzene and dioxolane rings is 0.20 (7)° in one molecule and 0.31 (7)° in the other. In the crystal, the two molecules are linked into dimers through pairwise O—H⋯N hydrogen bonds, with these units being formed into stacks by two different sets of aromatic π-stacking interactions. The stacks are connected by C—H⋯O hydrogen bonds. A Hirshfeld surface analysis indicates that the most significant contacts in the crystal packing are H⋯O/O⋯H (36.7%), H⋯H (32.2%) and C⋯H/H⋯C (12.7%).
of the title molecule, CKeywords: synthesis; crystal structure; benzodioxolane; oxime; O—H⋯N; C—H⋯O; hydrogen bonds; π-stacking; Hirshfeld surface analysis..
CCDC reference: 2262070
1. Chemical context
Oxime compounds containing an R2C=N—OH have been studied for many years because of their important role as acetylcholinesterase reactivators and their utility as therapeutic agents for various diseases (Musilek et al., 2011; Canario et al., 2018). Various have been identified in plants as biosynthetic intermediates and can facilitate a range of processes associated with plant growth and development (Sørensen et al., 2018). also have a wide range of biological activities, such as human immunodeficiency virus (HIV) agents that can inhibit HIV protease (Komai et al., 1997) and can act as anti-inflammatories (Li et al., 2018; Kwon et al., 2014). The introduction of an oxime group into an appropriate chemical backbone is a reasonable approach for the preparation of cytotoxic agents and many oxime derivatives have been reported to have therapeutic activity for cancer (Canario et al., 2018; Shen et al., 2015) and neurodegenerative disorders (Avrahami et al., 2013; Yuskaitis et al., 2009).
As part of our studies in this area, we now describe the synthesis, structure and Hirshfeld surface analysis of the title compound (I).
2. Structural commentary
The ) consists of two independent molecules differing slightly in the orientation of some hydrogen atoms. The benzodioxolane portion of the molecule containing O1 is planar to within 0.0171 (12) Å (r.m.s. deviation of the fitted atoms = 0.0091 Å) with C7 deviating by 0.0171 (12) Å from one side of the mean plane and O1 by 0.0170 (10) Å from the other, indicating a slight twist in the dioxolane ring. The corresponding portion of the second molecule containing O4 is planar to within 0.0041 (11) Å (r.m.s. deviation of the fitted atoms = 0.0030 Å), indicating a conformational difference, albeit small, between the two molecules. The overlay fit of inverted molecule 2 on molecule 1 is shown in Fig. 2 with the weighted r.m.s. fit of the 12 non-H atoms being 0.036 Å and showing the major differences to be in the hydrogen-atom positions. The C6—C1—C8—N1 and C1—C8—N1—O3 torsion angles are, respectively, 3.9 (2) and −179.96 (11)°, indicating the side chain to be nearly coplanar with the benzodioxolane unit. The corresponding torsion angles in the second molecule are virtually the same as above. The two molecules are connected into dimers through O3—H3A⋯N2 and O6—H6A⋯N1 hydrogen bonds (Table 1 and Fig. 1), generating R22(6) loops.
(Fig. 13. Supramolecular features
In the crystal, the dimers are connected into stacks extending along the [101] direction through slipped π-stacking interactions between the six-membered (Cg2: C1–C6 and Cg5: C9–C14) rings. For the C1–C6 rings, the centroid–centroid distance is 3.6024 (11) Å with a slippage of 1.185 Å between molecules at x, y, z and −x, −y + 1, −z. These paired molecules make weak, slipped π-stacking interactions with corresponding pairs at −x + 1, −y + 1, −z + 1 with a centroid–centroid distance of 3.8479 (11) Å and a slippage of 1.947 Å. The C9–C14 ring has slipped π-stacking interactions with its counterparts in molecules at x − , −y + , z − and at x + , −y + , z + with centroid–centroid distances of 3.8380 (11) Å and dihedral angles of 2.41 (6)° for both. The slippages for these interactions (Fig. 3) are 1.572 and 1.662 Å, respectively. These differences in the π-stacking interactions also support the independence of the two molecules in the The stacks are associated through C7—H7B⋯O4, C8—H8⋯O6, C15—H15A⋯O1 and C16—H16⋯O3 hydrogen bonds (Table 1 and Fig. 4).
4. Database survey
A search using CCDC ConQuest of the Cambridge Structural Database (CSD, Version 5.44, updated to April 2023; Groom et al., 2016) using the title molecule with all hydrogen atoms deleted gave 26 hits. Most of these contain the search fragment as part of a larger, often polycyclic molecule, but three are considered similar to (I). These are N-[1-(2,2-dimethyl-2H-1,3-benzodioxol-5-yl)-2-(1H-imidazol-1-yl)ethylidene]hydroxylamine (CSD refcode: GAVWUZ; Ren et al., 2022), in which the benzo[d][1,3]dioxole unit is similar to that in (I), 1-(1,3-benzodioxol-5-yl)-N-hydroxy-3-(1H-imidazol-1-yl)propan-1-imine isopropanol solvate (QEKMAX; Al-Wabli et al., 2017), in which the benzo[d][1,3]dioxole-5-carbaldehydeoxime takes a (Z) form and (Z)-3,4-methylenedioxybenzaldehyde oximium 4-toluenesulfonate (VADDIN; Jerslev et al., 1988), in which the benzo[d][1,3]dioxole unit is similar to that in (I).
5. Hirshfeld surface analysis
The Hirshfeld surface analysis was performed with Crystal Explorer (Version 21.5; Spackman et al., 2021). Fig. 5 shows views of the dnorm surfaces for the two molecules in the plotted over the limits from −0.63 to 1.18 a.u for molecule 1 and −0.63 to 1.07 a.u for molecule 2. The O—H⋯N hydrogen bonds, which generate the dimers are indicated by the bright-red spots in Fig. 5(a) and 5(b), respectively. Fig. 6 presents the two-dimensional fingerprint plots involving all intermolecular interactions [Fig. 6(a)] and delineated into C⋯H/H⋯C [Fig. 6(c)], and H⋯O/O⋯H [Fig. 6(h)] interactions. For completeness, the H⋯H interactions constitute 32.2% of the surface [Fig. 6(b)]. The other interactions contribute small amounts, viz., C⋯N/N⋯C (1.0%), C⋯O/O⋯C (2.4%), C⋯C (9.5%), H⋯N/N⋯H (4.1%), N⋯O/O⋯N (1.1%), N⋯N (0.0%) and O⋯O (0.4%).
6. Synthesis and crystallization
A solution of 5.0 g of sodium hydroxide dissolved in 20 ml of water was mixed with 8.0 g of hydroxylamine hydrochloride dissolved in 15 ml of water, then 8.0 g of benzo[d][1,3]dioxole-5-carbaldehyde dissolved in 50 ml of ethanol was added to the mixture. After 5 h of stirring at 273 K, the product was allowed to precipitate and then filtered with a yield of 90%. Single crystals were recrystallized from ethanol solution.
7. Refinement
Crystal data, data collection and structure . H atoms attached to carbon were placed in calculated positions (C—H = 0.95–0.99 Å) while those attached to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give O—H = 0.87 Å. All were included as riding contributions with isotropic displacement parameters 1.2–1.5 times those of the attached atoms.
details are summarized in Table 2
|
Supporting information
CCDC reference: 2262070
https://doi.org/10.1107/S2056989023004139/hb8064sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989023004139/hb8064Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989023004139/hb8064Isup3.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2056989023004139/hb8064Isup4.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: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012), PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b), PLATON (Spek, 2020) and publCIF (Westrip, 2010).C8H7NO3 | F(000) = 688 |
Mr = 165.15 | Dx = 1.459 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8724 (14) Å | Cell parameters from 6661 reflections |
b = 33.502 (7) Å | θ = 2.4–28.1° |
c = 7.3449 (15) Å | µ = 0.11 mm−1 |
β = 117.238 (3)° | T = 150 K |
V = 1503.6 (5) Å3 | Plate, colourless |
Z = 8 | 0.36 × 0.17 × 0.10 mm |
Bruker SMART APEX CCD diffractometer | 3858 independent reflections |
Radiation source: fine-focus sealed tube | 2836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.7°, θmin = 2.4° |
φ and ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −45→43 |
Tmin = 0.82, Tmax = 0.99 | l = −9→9 |
28032 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: mixed |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0621P)2 + 0.2227P] where P = (Fo2 + 2Fc2)/3 |
3858 reflections | (Δ/σ)max < 0.001 |
217 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | 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, collected 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.99 Å) while those attached to oxygen were placed in locations derived from a difference map and their coordinates adjusted to give O—H = 0.87 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 | ||
O1 | 0.21075 (18) | 0.58110 (3) | 0.12890 (17) | 0.0385 (3) | |
O2 | 0.50131 (18) | 0.54433 (3) | 0.13879 (17) | 0.0377 (3) | |
O3 | 0.40957 (17) | 0.36128 (3) | 0.45505 (17) | 0.0377 (3) | |
H3A | 0.516808 | 0.349351 | 0.445154 | 0.057* | |
N1 | 0.43129 (18) | 0.40031 (3) | 0.39281 (18) | 0.0287 (3) | |
C1 | 0.2551 (2) | 0.46413 (4) | 0.30915 (19) | 0.0254 (3) | |
C2 | 0.0814 (2) | 0.48668 (4) | 0.3030 (2) | 0.0290 (3) | |
H2 | −0.020388 | 0.474321 | 0.339202 | 0.035* | |
C3 | 0.0524 (2) | 0.52685 (4) | 0.2452 (2) | 0.0316 (3) | |
H3 | −0.065828 | 0.542093 | 0.241589 | 0.038* | |
C4 | 0.2043 (2) | 0.54306 (4) | 0.1939 (2) | 0.0280 (3) | |
C5 | 0.3775 (2) | 0.52084 (4) | 0.1994 (2) | 0.0262 (3) | |
C6 | 0.4081 (2) | 0.48172 (4) | 0.25517 (19) | 0.0252 (3) | |
H6 | 0.527136 | 0.466906 | 0.257669 | 0.030* | |
C7 | 0.4031 (3) | 0.58311 (4) | 0.0990 (3) | 0.0379 (4) | |
H7A | 0.363159 | 0.591287 | −0.043339 | 0.045* | |
H7B | 0.507199 | 0.602939 | 0.193416 | 0.045* | |
C8 | 0.2711 (2) | 0.42252 (4) | 0.3722 (2) | 0.0285 (3) | |
H8 | 0.159251 | 0.411565 | 0.398925 | 0.034* | |
O4 | 0.79029 (19) | 0.15551 (3) | 0.4126 (2) | 0.0489 (3) | |
O5 | 0.54405 (19) | 0.19665 (3) | 0.4559 (2) | 0.0488 (3) | |
O6 | 0.84324 (18) | 0.38394 (3) | 0.42029 (17) | 0.0392 (3) | |
H6A | 0.725059 | 0.395443 | 0.409864 | 0.059* | |
N2 | 0.78297 (19) | 0.34360 (4) | 0.42083 (18) | 0.0299 (3) | |
C9 | 0.8894 (2) | 0.27623 (4) | 0.4103 (2) | 0.0266 (3) | |
C10 | 1.0360 (2) | 0.25112 (4) | 0.3838 (2) | 0.0319 (3) | |
H10 | 1.152810 | 0.262583 | 0.366388 | 0.038* | |
C11 | 1.0166 (2) | 0.20967 (5) | 0.3820 (2) | 0.0354 (3) | |
H11 | 1.116764 | 0.192674 | 0.363450 | 0.043* | |
C12 | 0.8452 (2) | 0.19468 (4) | 0.4082 (2) | 0.0320 (3) | |
C13 | 0.6986 (2) | 0.21941 (4) | 0.4347 (2) | 0.0302 (3) | |
C14 | 0.7148 (2) | 0.25990 (4) | 0.4373 (2) | 0.0292 (3) | |
H14 | 0.613289 | 0.276437 | 0.456418 | 0.035* | |
C15 | 0.5989 (3) | 0.15609 (4) | 0.4420 (2) | 0.0369 (3) | |
H15A | 0.476274 | 0.142790 | 0.325521 | 0.044* | |
H15B | 0.626735 | 0.141616 | 0.569104 | 0.044* | |
C16 | 0.9197 (2) | 0.31931 (4) | 0.4083 (2) | 0.0299 (3) | |
H16 | 1.043047 | 0.329466 | 0.397484 | 0.036* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0392 (6) | 0.0285 (6) | 0.0509 (7) | 0.0074 (4) | 0.0234 (5) | 0.0055 (5) |
O2 | 0.0400 (6) | 0.0297 (6) | 0.0560 (7) | 0.0021 (4) | 0.0328 (5) | 0.0076 (5) |
O3 | 0.0355 (6) | 0.0243 (5) | 0.0599 (7) | −0.0013 (4) | 0.0277 (5) | 0.0051 (5) |
N1 | 0.0266 (6) | 0.0231 (6) | 0.0357 (6) | −0.0034 (4) | 0.0137 (5) | −0.0002 (5) |
C1 | 0.0204 (6) | 0.0296 (7) | 0.0245 (6) | −0.0017 (5) | 0.0088 (5) | −0.0042 (5) |
C2 | 0.0205 (7) | 0.0358 (8) | 0.0324 (7) | −0.0030 (5) | 0.0137 (6) | −0.0045 (6) |
C3 | 0.0223 (7) | 0.0361 (8) | 0.0373 (8) | 0.0048 (6) | 0.0144 (6) | −0.0047 (6) |
C4 | 0.0270 (7) | 0.0264 (7) | 0.0282 (7) | 0.0034 (5) | 0.0105 (6) | −0.0011 (5) |
C5 | 0.0240 (7) | 0.0308 (7) | 0.0257 (6) | −0.0017 (5) | 0.0131 (5) | −0.0023 (5) |
C6 | 0.0212 (6) | 0.0281 (7) | 0.0275 (7) | 0.0020 (5) | 0.0121 (5) | −0.0020 (5) |
C7 | 0.0463 (9) | 0.0327 (8) | 0.0414 (9) | 0.0046 (7) | 0.0259 (7) | 0.0068 (6) |
C8 | 0.0229 (7) | 0.0298 (7) | 0.0343 (7) | −0.0043 (5) | 0.0143 (6) | −0.0035 (6) |
O4 | 0.0423 (7) | 0.0275 (6) | 0.0825 (9) | 0.0000 (5) | 0.0335 (7) | −0.0056 (5) |
O5 | 0.0397 (6) | 0.0279 (6) | 0.0940 (10) | −0.0066 (5) | 0.0439 (7) | −0.0038 (6) |
O6 | 0.0347 (6) | 0.0276 (6) | 0.0612 (7) | −0.0021 (4) | 0.0269 (5) | 0.0071 (5) |
N2 | 0.0272 (6) | 0.0265 (6) | 0.0360 (6) | −0.0026 (5) | 0.0145 (5) | 0.0037 (5) |
C9 | 0.0208 (6) | 0.0313 (7) | 0.0277 (7) | −0.0005 (5) | 0.0110 (5) | 0.0000 (5) |
C10 | 0.0214 (7) | 0.0408 (9) | 0.0354 (8) | 0.0005 (6) | 0.0147 (6) | −0.0002 (6) |
C11 | 0.0240 (7) | 0.0399 (9) | 0.0435 (8) | 0.0058 (6) | 0.0165 (6) | −0.0040 (6) |
C12 | 0.0265 (7) | 0.0287 (8) | 0.0377 (8) | 0.0025 (5) | 0.0119 (6) | −0.0026 (6) |
C13 | 0.0211 (7) | 0.0319 (8) | 0.0380 (8) | −0.0029 (5) | 0.0139 (6) | −0.0017 (6) |
C14 | 0.0227 (7) | 0.0296 (7) | 0.0371 (8) | 0.0011 (5) | 0.0154 (6) | −0.0017 (6) |
C15 | 0.0358 (8) | 0.0286 (8) | 0.0441 (9) | −0.0017 (6) | 0.0164 (7) | 0.0016 (6) |
C16 | 0.0237 (7) | 0.0357 (8) | 0.0331 (7) | −0.0029 (6) | 0.0153 (6) | 0.0023 (6) |
O1—C4 | 1.3685 (17) | O4—C12 | 1.3699 (18) |
O1—C7 | 1.4377 (19) | O4—C15 | 1.427 (2) |
O2—C5 | 1.3742 (16) | O5—C13 | 1.3730 (17) |
O2—C7 | 1.4311 (17) | O5—C15 | 1.4264 (18) |
O3—N1 | 1.4154 (15) | O6—N2 | 1.4140 (15) |
O3—H3A | 0.8702 | O6—H6A | 0.8701 |
N1—C8 | 1.2790 (18) | N2—C16 | 1.2776 (18) |
C1—C2 | 1.3957 (18) | C9—C10 | 1.3931 (19) |
C1—C6 | 1.4110 (18) | C9—C14 | 1.4129 (18) |
C1—C8 | 1.4570 (19) | C9—C16 | 1.4595 (19) |
C2—C3 | 1.398 (2) | C10—C11 | 1.394 (2) |
C2—H2 | 0.9500 | C10—H10 | 0.9500 |
C3—C4 | 1.373 (2) | C11—C12 | 1.373 (2) |
C3—H3 | 0.9500 | C11—H11 | 0.9500 |
C4—C5 | 1.3890 (19) | C12—C13 | 1.3849 (19) |
C5—C6 | 1.3603 (19) | C13—C14 | 1.3606 (19) |
C6—H6 | 0.9500 | C14—H14 | 0.9500 |
C7—H7A | 0.9900 | C15—H15A | 0.9900 |
C7—H7B | 0.9900 | C15—H15B | 0.9900 |
C8—H8 | 0.9500 | C16—H16 | 0.9500 |
C4—O1—C7 | 106.02 (11) | C12—O4—C15 | 105.87 (11) |
C5—O2—C7 | 106.39 (11) | C13—O5—C15 | 106.11 (11) |
N1—O3—H3A | 100.3 | N2—O6—H6A | 99.2 |
C8—N1—O3 | 111.31 (11) | C16—N2—O6 | 112.48 (11) |
C2—C1—C6 | 120.04 (13) | C10—C9—C14 | 120.06 (13) |
C2—C1—C8 | 117.85 (12) | C10—C9—C16 | 118.69 (12) |
C6—C1—C8 | 122.10 (12) | C14—C9—C16 | 121.24 (12) |
C1—C2—C3 | 122.15 (13) | C9—C10—C11 | 122.04 (13) |
C1—C2—H2 | 118.9 | C9—C10—H10 | 119.0 |
C3—C2—H2 | 118.9 | C11—C10—H10 | 119.0 |
C4—C3—C2 | 116.33 (12) | C12—C11—C10 | 116.57 (13) |
C4—C3—H3 | 121.8 | C12—C11—H11 | 121.7 |
C2—C3—H3 | 121.8 | C10—C11—H11 | 121.7 |
O1—C4—C3 | 127.89 (13) | O4—C12—C11 | 128.09 (13) |
O1—C4—C5 | 110.19 (12) | O4—C12—C13 | 110.11 (13) |
C3—C4—C5 | 121.91 (13) | C11—C12—C13 | 121.80 (14) |
C6—C5—O2 | 128.03 (12) | C14—C13—O5 | 127.91 (12) |
C6—C5—C4 | 122.51 (12) | C14—C13—C12 | 122.58 (13) |
O2—C5—C4 | 109.45 (12) | O5—C13—C12 | 109.51 (13) |
C5—C6—C1 | 117.05 (12) | C13—C14—C9 | 116.94 (12) |
C5—C6—H6 | 121.5 | C13—C14—H14 | 121.5 |
C1—C6—H6 | 121.5 | C9—C14—H14 | 121.5 |
O2—C7—O1 | 107.86 (11) | O5—C15—O4 | 108.40 (12) |
O2—C7—H7A | 110.1 | O5—C15—H15A | 110.0 |
O1—C7—H7A | 110.1 | O4—C15—H15A | 110.0 |
O2—C7—H7B | 110.1 | O5—C15—H15B | 110.0 |
O1—C7—H7B | 110.1 | O4—C15—H15B | 110.0 |
H7A—C7—H7B | 108.4 | H15A—C15—H15B | 108.4 |
N1—C8—C1 | 122.00 (12) | N2—C16—C9 | 121.07 (12) |
N1—C8—H8 | 119.0 | N2—C16—H16 | 119.5 |
C1—C8—H8 | 119.0 | C9—C16—H16 | 119.5 |
C6—C1—C2—C3 | −0.3 (2) | C14—C9—C10—C11 | 0.2 (2) |
C8—C1—C2—C3 | 179.76 (13) | C16—C9—C10—C11 | −179.38 (13) |
C1—C2—C3—C4 | 0.2 (2) | C9—C10—C11—C12 | −0.2 (2) |
C7—O1—C4—C3 | 179.08 (14) | C15—O4—C12—C11 | −179.48 (15) |
C7—O1—C4—C5 | −2.05 (15) | C15—O4—C12—C13 | 0.38 (16) |
C2—C3—C4—O1 | 178.64 (13) | C10—C11—C12—O4 | −179.98 (14) |
C2—C3—C4—C5 | −0.1 (2) | C10—C11—C12—C13 | 0.2 (2) |
C7—O2—C5—C6 | −179.40 (14) | C15—O5—C13—C14 | 179.94 (14) |
C7—O2—C5—C4 | 1.47 (15) | C15—O5—C13—C12 | 0.07 (17) |
O1—C4—C5—C6 | −178.80 (12) | O4—C12—C13—C14 | 179.83 (13) |
C3—C4—C5—C6 | 0.1 (2) | C11—C12—C13—C14 | −0.3 (2) |
O1—C4—C5—O2 | 0.38 (16) | O4—C12—C13—O5 | −0.29 (17) |
C3—C4—C5—O2 | 179.33 (12) | C11—C12—C13—O5 | 179.58 (14) |
O2—C5—C6—C1 | −179.25 (13) | O5—C13—C14—C9 | −179.49 (14) |
C4—C5—C6—C1 | −0.2 (2) | C12—C13—C14—C9 | 0.4 (2) |
C2—C1—C6—C5 | 0.29 (19) | C10—C9—C14—C13 | −0.3 (2) |
C8—C1—C6—C5 | −179.76 (12) | C16—C9—C14—C13 | 179.28 (13) |
C5—O2—C7—O1 | −2.71 (15) | C13—O5—C15—O4 | 0.16 (17) |
C4—O1—C7—O2 | 2.92 (15) | C12—O4—C15—O5 | −0.33 (16) |
O3—N1—C8—C1 | −179.96 (11) | O6—N2—C16—C9 | 178.85 (11) |
C2—C1—C8—N1 | −176.17 (13) | C10—C9—C16—N2 | 176.16 (13) |
C6—C1—C8—N1 | 3.9 (2) | C14—C9—C16—N2 | −3.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···N2 | 0.87 | 1.93 | 2.7549 (16) | 158 |
C7—H7B···O4i | 0.99 | 2.58 | 3.239 (2) | 124 |
C8—H8···O6ii | 0.95 | 2.43 | 3.3754 (18) | 173 |
O6—H6A···N1 | 0.87 | 1.97 | 2.7989 (17) | 158 |
C15—H15A···O1iii | 0.99 | 2.54 | 3.1775 (19) | 122 |
C16—H16···O3iv | 0.95 | 2.59 | 3.5173 (18) | 167 |
Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x−1, y, z; (iii) −x+1/2, y−1/2, −z+1/2; (iv) x+1, y, z. |
Acknowledgements
JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
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