Syntheses and crystal structures of the imides 4-(2-phenyl­eth­yl)- and 4-[2-(4-hy­droxy­phen­yl)eth­yl]-4-aza­tetra­cyclo­[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione

Bajko, J.P.; Staples, R.J.; Biros, S.M.

doi:10.1107/S2056989024011253

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 80| Part 12| December 2024| Pages 1318-1321

https://doi.org/10.1107/S2056989024011253

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Syntheses and crystal structures of the imides 4-(2-phenylethyl)- and 4-[2-(4-hydroxyphenyl)ethyl]-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione

Jonathan P. Bajko,^a Richard J. Staples ^b and Shannon M. Biros ^a ^*

^aDepartment of Chemistry, Grand Valley State University, Allendale, MI 49401, USA, and ^bCenter for Crystallographic Research, Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA
^*Correspondence e-mail: biross@gvsu.edu

Edited by M. Weil, Vienna University of Technology, Austria (Received 4 November 2024; accepted 19 November 2024; online 28 November 2024)

The syntheses and characterization (NMR and XRD) of two substituted [2.2.2]bicyclooctene ring systems are described here. The cyclohexene rings of these systems adopt a nearly perfect boat conformation according to analysis using Cremer–Pople parameters. Both structures contain a nearly planar imide ring that is oriented endo relative to a bridgehead cyclopropyl ring. 4-(2-Phenylethyl)-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione, C₁₉H₁₉NO₂, is substituted with a phenylethyl group that hosts C—H⋯π interactions in the crystal. 4-[2-(4-Hydroxyphenyl)ethyl]-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione, C₁₉H₁₉NO₃, bears a 4-hydroxyphenylethyl group on the imide ring and contains O—H⋯O and C—H⋯O hydrogen bonds.

Keywords: crystal structure; imide; tricylic compound; C—H⋯O hydrogen bond; C—H⋯π interaction.

CCDC references: 2403867; 2403866

1. Chemical context

Diels–Alder adduct a was first reported in 1939 (Fig. 1; Kohler et al., 1939 ), however its structure was not unambiguously determined until nearly 15 years later (Alder & Jacobs, 1953 ). In 2020, Winchester and co-workers reported the crystal structure of a in this journal (Hulsman et al., 2020 ). Anhydride a can be easily modified to give the corresponding imides b by heating with a primary amine. Previous work has shown that this rigid, tricyclic structure can serve as a scaffold for the design of new compounds with antiviral activity. One interesting imide derivative is compound c, Tecovirimat (Bailey et al., 2007 ; Hughes 2019 ), which has been approved as a treatment for smallpox.

Figure 1
Structures of compounds a–c related to this work.

Our interest in this chemistry is the use of this series of reactions in an upper-level undergraduate advanced organic chemistry laboratory course (Kurtz & Johnson, 1989 ). The tricyclic Diels–Alder adduct a is pedagogically useful for in-depth analysis by NMR spectroscopy, and the imides b are easily prepared and have turned out to be crystalline. In this context, we report here the syntheses, NMR characterizations and crystal structures of two of these imides, I, C₁₉H₁₉NO₂, and II, C₁₉H₁₉NO₃.

2. Structural commentary

The molecular structure of compound I is shown in Fig. 2 along with its atom-labeling scheme. The imide ring (–N1–C1–C3–C4–C2–) is nearly planar with a Cremer–Pople τ value of 1.8 (Cremer & Pople, 1975 ) and is oriented endo relative to the bridgehead cyclopropyl ring (–C9—C10—C11–). The carbonyl groups of the imide rings have bond lengths of 1.216 (2) and 1.214 (2) Å, with C—N bond lengths of 1.383 (2) and 1.390 (2) Å in the ring. The phenylethyl substituent on the imide nitrogen N1 is oriented in a nearly perfect anti conformation around the C12—C13 bond with an N1—C12—C13—C14 torsion angle of −177.61 (13)°. The N1—C12 bond is slightly longer than the N—C(O) bond at 1.458 (2) Å. The cyclopropane ring has C—C bond lengths ranging from 1.507 (3) to 1.515 (2) Å with C—C—C bond angles ranging from 59.71 (12) to 60.29 (12)°. The cyclohexene ring system (-C3–C8–C7–C6–C5–C4-) has Cremer–Pople puckering parameters of 90.46 (13) and 299.31 (13)° for θ and φ, respectively, indicating that this ring is in a nearly perfect boat conformation. The alkene group (C6=C7) of this cyclohexene ring has a bond length of 1.329 (2) Å.

Figure 2
The molecular structure of compound I along with the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level using standard CPK colors. Hydrogen atoms are shown as spheres of arbitrary size.

The molecular structure of compound II (Fig. 3) is, unsurprisingly, very similar to that of compound I. The imide ring (–N1–C1–C3–C4–C2–) again is planar and oriented endo relative to the cyclopropyl bridgehead carbon atoms C9 and C10. The key bond lengths and angles of this compound are nearly identical (within error) to those described above for compound I. The 2-ethyl-(4-hydroxyphenyl) substituent bonded to the imide nitrogen atom N1 again adopts an anti conformation around the ethyl C12—C13 bond with an N1—C12—C13—C14 torsion angle of −176.50 (10)°. The hydrogen atom of the phenol group (H3) is nearly coplanar with the atoms of the aromatic ring C14–C19 with a H3—O3—C17–C18 torsion angle of −1.4 (15)°.

Figure 3
The molecular structure of compound II along with the atom-labeling scheme. Displacement ellipsoids are shown at the 50% probability level using standard CPK colors. Hydrogen atoms are shown as spheres of arbitrary size.

3. Supramolecular features

The predominant intermolecular forces present in the crystal of compound I are C—H⋯π interactions between C11(H11A) and C12(H12B) and the centroid (Cg) of aromatic ring C14–C19 (Fig. 4, Table 1). Molecules of compound I are arranged into supramolecular sheets that lie in the ab plane.

Table 1
Hydrogen-bond geometry (Å, °) for I

Cg denotes the centroid of the C14-C19 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11ⁱ—H11A⋯Cg	0.99	2.98	3.744 (2)	135
C12ⁱⁱ—H12B⋯Cg	0.99	2.92	3.4608 (19)	115
Symmetry codes: (i) $[x-{\script{3\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) .

Figure 4
Depiction of C—H⋯π interactions (blue dashed lines) present in the crystal of compound I using standard CPK colors and a ball-and-stick model. For clarity, only those hydrogen atoms that are involved in a C—H⋯π interaction are shown. [Symmetry codes: (i) x − $[{3\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ ; (ii) −x + 1, −y + 1, −z + 1; (iii) x − $[{1\over 2}]$ , −y + $[{3\over 2}]$ , z + $[{1\over 2}]$ .]

The crystal of compound II contains classical O—H⋯O and non-classical C—H⋯O hydrogen bonds (Sutor, 1962 , 1963 ; Steiner, 1996 ) with the carbonyl oxygen atoms O1 and O2 as acceptors (Table 2). The classical O—H⋯O hydrogen bond has expectedly shorter H—A and D⋯A distances than the C—H⋯O hydrogen bonds. The hydrogen bonds between atoms H3 and O1 form centrosymmetric dimers in the crystal of compound II. These dimers are linked into columns via the H13A⋯O2 interactions that run along the a-axis direction (Fig. 5). These columns are then connected into a complex tri-periodic network via C—H⋯O interactions between H6 and O1.

Table 2
Hydrogen-bond geometry (Å, °) for II

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.92 (2)	1.98 (2)	2.8955 (13)	172 (2)
C13—H13A⋯O2ⁱⁱ	0.99	2.52	3.4396 (16)	154
C6—H6⋯O1ⁱⁱⁱ	0.95	2.50	3.4473 (15)	176
Symmetry codes: (i) ; (ii) ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 5
A depiction of the hydrogen-bonded columns present in the crystal of compound II using a ball-and-stick model with standard CPK colors. Hydrogen bonds are shown with blue dashed lines; only those hydrogen atoms involved in a hydrogen bond are shown for clarity. [Symmetry codes: (i) −x, −y + 1, −z + 1; (ii) x - 1, y, z.]

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.45, updates through June 2024, Groom et al., 2016 ) for structures containing the tricyclic ring system shared by compounds I and II and substituted with carbonyl groups at the appropriate positions returned 16 hits. These hits include anhydride a (HOKRIK and HOKRIK01; White & Goh, 2014 ; Hulsman et al., 2020) along with two imides b where the substituents are a p-bromophenyl ring (NUTTEE; Hulsman et al., 2020) and an isoxazolidine ring (LULVUM; Efremova et al., 2020 ). Also found in this subgroup of crystal structures is tecovirimat c (UPUDOZ; Zhou et al., 2010 ) along with a derivative of c where the –CF₃ group has been replaced with a –Br atom (SOKVIY; Bailey et al., 2007). An interesting hit is VONCEG (Menzek et al., 1991 ), which bears a substituted cycloheptatriene ring fused to the tricyclic core of anhydride a.

5. Synthesis and crystallization

Synthesis of imides I and II: Diels–Alder anhydride adduct a (50 mg, 0.26 mmol) was dissolved in 0.5 ml of xylenes in a small vial at ambient temperature. In a separate small vial at ambient temperature, an equimolar amount of either phenethylamine (for I) or tyramine (for II) was dissolved in 0.5 ml of xylenes and then transferred dropwise to the solution of the anhydride. The reaction mixture was heated to reflux with stirring for 30 minutes and then allowed to cool to room temperature. The stir bar was removed, and the reaction mixture was diluted with slow addition of 5 ml of hexanes. The product imide crystallized out of solution upon standing overnight.

I: ¹H-NMR (400 MHz, chloroform-d) δ 7.26 (m, 2H), 7.19 (m, 3H), 5.59 (m, 2H), 3.62 (m, 2H), 3.33 (m, 2H), 2.90 (m, 2H), 2.76 (t, J = 8.0 Hz, 2H), 1.05 (m, 2H), 0.24 (m, 1H), 0.19 (m, 1H); ¹³C-NMR (100 MHz, chloroform-d) δ 178.5, 137.9, 129.0, 128.5, 127.6, 126.6, 45.3, 39.5, 33.6, 33.5, 9.9, 4.8.

II: ¹H-NMR (400 MHz, DMSO-d₆) δ 9.19 (s, 1H, –OH), 6.88 (d, J = 8.4 Hz, 2H), 6.60 (d, J = 8.4 Hz, 2H), 5.55 (m, 2H), 3.37 (m, 2H), 3.13 (m, 2H), 2.94 (m, 2H), 2.49 (m, 2H), 1.06 (m, 2H), 0.17 (m, 1H), −0.02 (m, 1H); ¹³C-NMR (100 MHz, DMSO-d₆) δ 178.5, 156.3, 130.1, 128.5, 127.8, 115.6, 45.1, 40.6, 33.4, 32.6, 10.0, 4.9.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. All hydrogen atoms bonded to carbon atoms were placed in calculated positions and refined as riding: C—H = 0.95–1.00 Å with U_iso(H) = 1.2U_eq(C) for methylene, methine, aromatic and alkene groups. In the structure of compound II, hydrogen atom H3 (which is part of the hydroxy group) was located using electron-density difference maps and refined freely.

Table 3
Experimental details

	I	II
Crystal data
Chemical formula	C₁₉H₁₉NO₂	C₁₉H₁₉NO₃
M_r	293.35	309.35
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/n
Temperature (K)	100	100
a, b, c (Å)	6.1340 (2), 21.2794 (8), 11.4373 (3)	6.19482 (10), 20.3854 (3), 12.4574 (2)
β (°)	95.625 (3)	103.3334 (16)
V (Å³)	1485.70 (8)	1530.76 (4)
Z	4	4
Radiation type	Cu Kα	Cu Kα
μ (mm⁻¹)	0.67	0.73
Crystal size (mm)	0.28 × 0.07 × 0.03	0.25 × 0.05 × 0.03

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )	Gaussian (CrysAlis PRO; Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.816, 1.000	0.831, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11251, 3094, 2481	24225, 3219, 2738
R_int	0.068	0.053
(sin θ/λ)_max (Å⁻¹)	0.633	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.149, 1.05	0.037, 0.099, 1.03
No. of reflections	3094	3219
No. of parameters	199	212
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.32	0.24, −0.19
Computer programs: CrysAlis PRO (Rigaku OD, 2023 $[Rigaku OD (2023). CrysAlis PRO. Rigaku Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), CrystalMaker (Palmer, 2007 ) and OLEX2 (Dolomanov et al., 2009 ; Bourhis et al., 2015 ).

Supporting information

CCDC references: 2403867; 2403866

Crystal structure: contains datablocks I, II. DOI: https://doi.org/10.1107/S2056989024011253/wm5740sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989024011253/wm5740Isup2.hkl

Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989024011253/wm5740IIsup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989024011253/wm5740Isup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989024011253/wm5740IIsup5.cml

checkCIF report

Computing details top

4-(2-Phenylethyl)-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione (I) top

Crystal data top

C₁₉H₁₉NO₂	F(000) = 624
M_r = 293.35	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.1340 (2) Å	Cell parameters from 5833 reflections
b = 21.2794 (8) Å	θ = 4.1–76.8°
c = 11.4373 (3) Å	µ = 0.67 mm⁻¹
β = 95.625 (3)°	T = 100 K
V = 1485.70 (8) Å³	Irregular, colourless
Z = 4	0.28 × 0.07 × 0.03 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3094 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2481 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.068
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.2°, θ_min = 4.2°
ω scans	h = −7→7
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	k = −26→26
T_min = 0.816, T_max = 1.000	l = −14→13
11251 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.052	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0696P)² + 0.6093P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3094 reflections	Δρ_max = 0.28 e Å⁻³
199 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.1032 (2)	0.67788 (7)	0.42612 (11)	0.0319 (3)
O2	0.7405 (2)	0.66698 (6)	0.66530 (11)	0.0330 (3)
N1	0.4237 (2)	0.65809 (7)	0.54138 (12)	0.0245 (3)
C1	0.2421 (3)	0.69384 (8)	0.50360 (14)	0.0241 (4)
C2	0.5649 (3)	0.68831 (8)	0.62579 (15)	0.0256 (4)
C3	0.2536 (3)	0.75512 (8)	0.56981 (14)	0.0236 (4)
H3	0.123802	0.759793	0.615613	0.028*
C4	0.4672 (3)	0.75100 (8)	0.65382 (14)	0.0231 (4)
H4	0.433452	0.752250	0.737575	0.028*
C5	0.6221 (3)	0.80617 (8)	0.62777 (15)	0.0246 (4)
H5	0.763479	0.804214	0.679197	0.030*
C6	0.6582 (3)	0.80049 (9)	0.49988 (15)	0.0261 (4)
H6	0.799403	0.795115	0.473882	0.031*
C7	0.4770 (3)	0.80360 (8)	0.42621 (15)	0.0243 (4)
H7	0.478006	0.800593	0.343395	0.029*
C8	0.2696 (3)	0.81229 (8)	0.48505 (15)	0.0236 (4)
H8	0.138189	0.815029	0.426211	0.028*
C9	0.2871 (3)	0.86951 (8)	0.56640 (15)	0.0273 (4)
H9	0.150156	0.882946	0.600205	0.033*
C10	0.4937 (3)	0.86586 (8)	0.65038 (15)	0.0269 (4)
H10	0.480218	0.877117	0.734259	0.032*
C11	0.4636 (3)	0.91838 (9)	0.56136 (16)	0.0306 (4)
H11A	0.434327	0.961057	0.590545	0.037*
H11B	0.552811	0.917114	0.493804	0.037*
C12	0.4735 (3)	0.59815 (8)	0.48821 (15)	0.0266 (4)
H12A	0.335405	0.575070	0.466226	0.032*
H12B	0.564550	0.572440	0.546295	0.032*
C13	0.5946 (3)	0.60743 (9)	0.37955 (16)	0.0281 (4)
H13A	0.506493	0.634553	0.322642	0.034*
H13B	0.735919	0.628814	0.401942	0.034*
C14	0.6365 (3)	0.54518 (8)	0.32266 (14)	0.0243 (4)
C15	0.8332 (3)	0.51322 (9)	0.34909 (16)	0.0307 (4)
H15	0.945359	0.531513	0.401466	0.037*
C16	0.8672 (3)	0.45473 (10)	0.29953 (19)	0.0388 (5)
H16	1.001862	0.433229	0.318270	0.047*
C17	0.7048 (4)	0.42793 (10)	0.22293 (19)	0.0410 (5)
H17	0.727929	0.387999	0.189122	0.049*
C18	0.5090 (4)	0.45915 (10)	0.19556 (17)	0.0381 (5)
H18	0.397671	0.440800	0.142784	0.046*
C19	0.4755 (3)	0.51726 (9)	0.24523 (16)	0.0305 (4)
H19	0.340323	0.538453	0.226201	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0239 (6)	0.0413 (8)	0.0283 (7)	−0.0053 (5)	−0.0082 (5)	−0.0036 (5)
O2	0.0311 (7)	0.0350 (7)	0.0298 (7)	0.0080 (5)	−0.0131 (5)	−0.0025 (5)
N1	0.0244 (7)	0.0273 (8)	0.0207 (7)	0.0002 (5)	−0.0035 (5)	−0.0007 (5)
C1	0.0200 (7)	0.0305 (9)	0.0212 (8)	−0.0020 (6)	−0.0005 (6)	0.0025 (6)
C2	0.0266 (8)	0.0297 (9)	0.0189 (7)	0.0011 (6)	−0.0061 (6)	−0.0003 (6)
C3	0.0183 (7)	0.0309 (9)	0.0208 (7)	0.0002 (6)	−0.0029 (6)	0.0008 (6)
C4	0.0222 (8)	0.0279 (9)	0.0180 (7)	0.0015 (6)	−0.0043 (6)	0.0000 (6)
C5	0.0193 (7)	0.0299 (9)	0.0227 (8)	−0.0011 (6)	−0.0078 (6)	−0.0010 (6)
C6	0.0201 (8)	0.0313 (9)	0.0266 (8)	−0.0003 (6)	0.0002 (6)	−0.0007 (7)
C7	0.0238 (8)	0.0294 (9)	0.0194 (7)	−0.0011 (6)	−0.0002 (6)	0.0010 (6)
C8	0.0177 (7)	0.0295 (9)	0.0223 (8)	0.0012 (6)	−0.0043 (6)	0.0018 (6)
C9	0.0255 (8)	0.0305 (9)	0.0251 (8)	0.0042 (7)	−0.0021 (7)	0.0009 (7)
C10	0.0276 (8)	0.0291 (9)	0.0226 (8)	0.0004 (7)	−0.0046 (7)	−0.0021 (6)
C11	0.0347 (9)	0.0272 (9)	0.0284 (9)	0.0006 (7)	−0.0040 (7)	0.0001 (7)
C12	0.0294 (8)	0.0267 (8)	0.0226 (8)	−0.0009 (7)	−0.0029 (7)	−0.0011 (6)
C13	0.0298 (8)	0.0282 (9)	0.0261 (8)	−0.0021 (7)	0.0008 (7)	−0.0004 (7)
C14	0.0243 (8)	0.0278 (9)	0.0206 (7)	−0.0008 (6)	0.0005 (6)	0.0021 (6)
C15	0.0242 (8)	0.0378 (10)	0.0296 (9)	0.0004 (7)	−0.0009 (7)	0.0070 (7)
C16	0.0360 (10)	0.0377 (11)	0.0448 (11)	0.0111 (8)	0.0145 (8)	0.0110 (9)
C17	0.0576 (13)	0.0301 (10)	0.0381 (10)	−0.0008 (9)	0.0196 (9)	−0.0033 (8)
C18	0.0474 (11)	0.0378 (11)	0.0284 (9)	−0.0086 (9)	−0.0001 (8)	−0.0063 (8)
C19	0.0286 (9)	0.0348 (10)	0.0266 (8)	−0.0008 (7)	−0.0043 (7)	0.0007 (7)

Geometric parameters (Å, º) top

O1—C1	1.216 (2)	C9—C11	1.507 (3)
O2—C2	1.214 (2)	C10—H10	1.0000
N1—C1	1.383 (2)	C10—C11	1.511 (2)
N1—C2	1.390 (2)	C11—H11A	0.9900
N1—C12	1.458 (2)	C11—H11B	0.9900
C1—C3	1.506 (2)	C12—H12A	0.9900
C2—C4	1.510 (2)	C12—H12B	0.9900
C3—H3	1.0000	C12—C13	1.522 (3)
C3—C4	1.550 (2)	C13—H13A	0.9900
C3—C8	1.565 (2)	C13—H13B	0.9900
C4—H4	1.0000	C13—C14	1.509 (3)
C4—C5	1.557 (2)	C14—C15	1.392 (2)
C5—H5	1.0000	C14—C19	1.393 (2)
C5—C6	1.506 (2)	C15—H15	0.9500
C5—C10	1.530 (2)	C15—C16	1.392 (3)
C6—H6	0.9500	C16—H16	0.9500
C6—C7	1.329 (2)	C16—C17	1.384 (3)
C7—H7	0.9500	C17—H17	0.9500
C7—C8	1.507 (2)	C17—C18	1.381 (3)
C8—H8	1.0000	C18—H18	0.9500
C8—C9	1.530 (2)	C18—C19	1.385 (3)
C9—H9	1.0000	C19—H19	0.9500
C9—C10	1.515 (2)

C1—N1—C2	113.00 (15)	C11—C9—C10	60.00 (11)
C1—N1—C12	123.10 (14)	C5—C10—H10	117.0
C2—N1—C12	123.54 (14)	C9—C10—C5	110.36 (14)
O1—C1—N1	124.01 (17)	C9—C10—H10	117.0
O1—C1—C3	127.11 (16)	C11—C10—C5	122.08 (15)
N1—C1—C3	108.82 (13)	C11—C10—C9	59.71 (11)
O2—C2—N1	123.73 (16)	C11—C10—H10	117.0
O2—C2—C4	127.40 (15)	C9—C11—C10	60.29 (12)
N1—C2—C4	108.83 (14)	C9—C11—H11A	117.7
C1—C3—H3	110.4	C9—C11—H11B	117.7
C1—C3—C4	104.95 (13)	C10—C11—H11A	117.7
C1—C3—C8	111.37 (14)	C10—C11—H11B	117.7
C4—C3—H3	110.4	H11A—C11—H11B	114.9
C4—C3—C8	109.12 (13)	N1—C12—H12A	109.3
C8—C3—H3	110.4	N1—C12—H12B	109.3
C2—C4—C3	104.33 (13)	N1—C12—C13	111.47 (15)
C2—C4—H4	110.5	H12A—C12—H12B	108.0
C2—C4—C5	111.29 (14)	C13—C12—H12A	109.3
C3—C4—H4	110.5	C13—C12—H12B	109.3
C3—C4—C5	109.47 (13)	C12—C13—H13A	109.5
C5—C4—H4	110.5	C12—C13—H13B	109.5
C4—C5—H5	111.5	H13A—C13—H13B	108.1
C6—C5—C4	106.02 (13)	C14—C13—C12	110.83 (15)
C6—C5—H5	111.5	C14—C13—H13A	109.5
C6—C5—C10	110.98 (14)	C14—C13—H13B	109.5
C10—C5—C4	105.06 (14)	C15—C14—C13	121.05 (16)
C10—C5—H5	111.5	C15—C14—C19	118.36 (17)
C5—C6—H6	122.6	C19—C14—C13	120.55 (16)
C7—C6—C5	114.74 (15)	C14—C15—H15	119.7
C7—C6—H6	122.6	C16—C15—C14	120.64 (17)
C6—C7—H7	122.8	C16—C15—H15	119.7
C6—C7—C8	114.39 (15)	C15—C16—H16	120.0
C8—C7—H7	122.8	C17—C16—C15	119.94 (18)
C3—C8—H8	111.5	C17—C16—H16	120.0
C7—C8—C3	106.75 (13)	C16—C17—H17	120.0
C7—C8—H8	111.5	C18—C17—C16	120.10 (19)
C7—C8—C9	110.95 (14)	C18—C17—H17	120.0
C9—C8—C3	104.29 (14)	C17—C18—H18	120.1
C9—C8—H8	111.5	C17—C18—C19	119.83 (18)
C8—C9—H9	116.8	C19—C18—H18	120.1
C10—C9—C8	110.42 (14)	C14—C19—H19	119.4
C10—C9—H9	116.8	C18—C19—C14	121.12 (17)
C11—C9—C8	122.26 (16)	C18—C19—H19	119.4
C11—C9—H9	116.8

O1—C1—C3—C4	−177.86 (17)	C5—C6—C7—C8	0.1 (2)
O1—C1—C3—C8	−59.9 (2)	C5—C10—C11—C9	96.28 (17)
O2—C2—C4—C3	174.98 (18)	C6—C5—C10—C9	51.69 (19)
O2—C2—C4—C5	57.0 (2)	C6—C5—C10—C11	−14.6 (2)
N1—C1—C3—C4	−0.50 (18)	C6—C7—C8—C3	−58.86 (19)
N1—C1—C3—C8	117.44 (15)	C6—C7—C8—C9	54.2 (2)
N1—C2—C4—C3	−2.65 (18)	C7—C8—C9—C10	−52.07 (19)
N1—C2—C4—C5	−120.61 (15)	C7—C8—C9—C11	14.6 (2)
N1—C12—C13—C14	−177.61 (13)	C8—C3—C4—C2	−117.59 (15)
C1—N1—C2—O2	−175.20 (17)	C8—C3—C4—C5	1.61 (18)
C1—N1—C2—C4	2.5 (2)	C8—C9—C10—C5	0.2 (2)
C1—N1—C12—C13	83.9 (2)	C8—C9—C10—C11	116.27 (17)
C1—C3—C4—C2	1.86 (17)	C8—C9—C11—C10	−96.44 (17)
C1—C3—C4—C5	121.06 (15)	C10—C5—C6—C7	−54.2 (2)
C1—C3—C8—C7	−60.75 (16)	C11—C9—C10—C5	−116.06 (17)
C1—C3—C8—C9	−178.27 (13)	C12—N1—C1—O1	2.8 (3)
C2—N1—C1—O1	176.20 (17)	C12—N1—C1—C3	−174.62 (15)
C2—N1—C1—C3	−1.3 (2)	C12—N1—C2—O2	−1.9 (3)
C2—N1—C12—C13	−88.81 (19)	C12—N1—C2—C4	175.86 (15)
C2—C4—C5—C6	57.84 (17)	C12—C13—C14—C15	−94.16 (19)
C2—C4—C5—C10	175.42 (13)	C12—C13—C14—C19	83.6 (2)
C3—C4—C5—C6	−56.97 (17)	C13—C14—C15—C16	177.59 (17)
C3—C4—C5—C10	60.61 (16)	C13—C14—C19—C18	−177.77 (18)
C3—C8—C9—C10	62.51 (17)	C14—C15—C16—C17	0.2 (3)
C3—C8—C9—C11	129.18 (16)	C15—C14—C19—C18	0.1 (3)
C4—C3—C8—C7	54.64 (17)	C15—C16—C17—C18	0.0 (3)
C4—C3—C8—C9	−62.88 (16)	C16—C17—C18—C19	−0.2 (3)
C4—C5—C6—C7	59.37 (19)	C17—C18—C19—C14	0.1 (3)
C4—C5—C10—C9	−62.47 (17)	C19—C14—C15—C16	−0.2 (3)
C4—C5—C10—C11	−128.74 (16)

Hydrogen-bond geometry (Å, º) top

Cg denotes the centroid of the C14-C19 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C11ⁱ—H11A···Cg	0.99	2.98	3.744 (2)	135
C12ⁱⁱ—H12B···Cg	0.99	2.92	3.4608 (19)	115

Symmetry codes: (i) x−3/2, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1.

4-[2-(4-Hydroxyphenyl)ethyl]-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione (II) top

Crystal data top

C₁₉H₁₉NO₃	F(000) = 656
M_r = 309.35	D_x = 1.342 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
a = 6.19482 (10) Å	Cell parameters from 11000 reflections
b = 20.3854 (3) Å	θ = 4.2–77.3°
c = 12.4574 (2) Å	µ = 0.73 mm⁻¹
β = 103.3334 (16)°	T = 100 K
V = 1530.76 (4) Å³	Needle, colourless
Z = 4	0.25 × 0.05 × 0.03 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3219 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2738 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.053
Detector resolution: 10.0000 pixels mm^-1	θ_max = 77.7°, θ_min = 4.2°
ω scans	h = −7→7
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2023)	k = −25→22
T_min = 0.831, T_max = 1.000	l = −15→15
24225 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0479P)² + 0.4204P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3219 reflections	Δρ_max = 0.24 e Å⁻³
212 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.22461 (14)	0.32415 (4)	0.34473 (7)	0.0282 (2)
O2	0.92166 (14)	0.32894 (5)	0.56437 (8)	0.0312 (2)
O3	0.22408 (16)	0.63973 (4)	0.76502 (7)	0.0283 (2)
N1	0.56517 (16)	0.33992 (5)	0.46177 (8)	0.0233 (2)
C1	0.4153 (2)	0.30627 (6)	0.38185 (9)	0.0226 (2)
C2	0.7694 (2)	0.30848 (6)	0.49296 (10)	0.0235 (3)
C3	0.52553 (19)	0.24518 (6)	0.35103 (9)	0.0220 (2)
H3A	0.532143	0.246899	0.271628	0.026*
C4	0.76183 (19)	0.24663 (6)	0.42573 (10)	0.0218 (2)
H4	0.874553	0.248648	0.379854	0.026*
C5	0.79950 (19)	0.18446 (6)	0.50036 (10)	0.0226 (3)
H5	0.948741	0.184960	0.552529	0.027*
C6	0.6156 (2)	0.18277 (6)	0.56081 (10)	0.0238 (3)
H6	0.642429	0.183069	0.639031	0.029*
C7	0.4127 (2)	0.18083 (6)	0.49618 (10)	0.0253 (3)
H7	0.282883	0.179131	0.524435	0.030*
C8	0.4050 (2)	0.18152 (6)	0.37461 (10)	0.0244 (3)
H8	0.249038	0.179731	0.329527	0.029*
C9	0.5462 (2)	0.12572 (6)	0.34451 (10)	0.0261 (3)
H9	0.534891	0.117643	0.264226	0.031*
C10	0.7766 (2)	0.12710 (6)	0.41887 (10)	0.0252 (3)
H10	0.903112	0.119695	0.382893	0.030*
C11	0.6262 (2)	0.06955 (6)	0.42227 (11)	0.0303 (3)
H11A	0.562029	0.064960	0.487680	0.036*
H11B	0.661504	0.027621	0.390032	0.036*
C12	0.5151 (2)	0.40098 (6)	0.51242 (10)	0.0246 (3)
H12A	0.390600	0.423331	0.461438	0.030*
H12B	0.646043	0.430232	0.523776	0.030*
C13	0.4537 (2)	0.38991 (6)	0.62283 (10)	0.0246 (3)
H13A	0.327791	0.358846	0.612991	0.030*
H13B	0.581309	0.370480	0.676067	0.030*
C14	0.39024 (19)	0.45416 (6)	0.66741 (9)	0.0218 (2)
C15	0.5441 (2)	0.49292 (6)	0.73957 (10)	0.0252 (3)
H15	0.690945	0.477136	0.766275	0.030*
C16	0.4865 (2)	0.55417 (6)	0.77310 (10)	0.0257 (3)
H16	0.593183	0.579772	0.822688	0.031*
C17	0.2723 (2)	0.57793 (6)	0.73392 (9)	0.0231 (3)
C18	0.11533 (19)	0.53920 (6)	0.66448 (10)	0.0242 (3)
H18	−0.032540	0.554538	0.639392	0.029*
C19	0.17502 (19)	0.47814 (6)	0.63190 (10)	0.0235 (3)
H19	0.066654	0.452024	0.584257	0.028*
H3	0.077 (4)	0.6475 (12)	0.7333 (18)	0.068 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0251 (4)	0.0331 (5)	0.0243 (4)	0.0062 (4)	0.0013 (3)	0.0008 (3)
O2	0.0250 (5)	0.0298 (5)	0.0357 (5)	−0.0029 (4)	0.0006 (4)	−0.0067 (4)
O3	0.0302 (5)	0.0249 (5)	0.0298 (5)	0.0027 (4)	0.0071 (4)	−0.0037 (3)
N1	0.0247 (5)	0.0229 (5)	0.0217 (5)	0.0018 (4)	0.0041 (4)	−0.0009 (4)
C1	0.0242 (6)	0.0260 (6)	0.0175 (5)	0.0013 (5)	0.0045 (4)	0.0021 (4)
C2	0.0223 (6)	0.0239 (6)	0.0244 (6)	−0.0012 (4)	0.0058 (4)	0.0003 (5)
C3	0.0224 (6)	0.0249 (6)	0.0183 (5)	0.0011 (4)	0.0036 (4)	−0.0015 (4)
C4	0.0198 (5)	0.0243 (6)	0.0221 (6)	−0.0004 (4)	0.0062 (4)	−0.0008 (4)
C5	0.0196 (5)	0.0247 (6)	0.0229 (6)	0.0009 (4)	0.0037 (4)	−0.0001 (4)
C6	0.0255 (6)	0.0250 (6)	0.0213 (6)	0.0004 (5)	0.0062 (5)	0.0010 (4)
C7	0.0226 (6)	0.0268 (6)	0.0280 (6)	−0.0005 (5)	0.0091 (5)	−0.0004 (5)
C8	0.0202 (6)	0.0271 (6)	0.0244 (6)	−0.0016 (5)	0.0020 (4)	−0.0030 (5)
C9	0.0266 (6)	0.0258 (6)	0.0248 (6)	−0.0012 (5)	0.0039 (5)	−0.0044 (5)
C10	0.0242 (6)	0.0242 (6)	0.0276 (6)	0.0010 (5)	0.0068 (5)	−0.0013 (5)
C11	0.0333 (7)	0.0236 (6)	0.0330 (7)	−0.0012 (5)	0.0059 (5)	−0.0020 (5)
C12	0.0294 (6)	0.0207 (6)	0.0237 (6)	0.0040 (5)	0.0060 (5)	−0.0003 (4)
C13	0.0272 (6)	0.0226 (6)	0.0237 (6)	0.0018 (5)	0.0054 (5)	0.0016 (5)
C14	0.0242 (6)	0.0224 (6)	0.0194 (5)	0.0009 (4)	0.0059 (4)	0.0023 (4)
C15	0.0215 (6)	0.0279 (6)	0.0248 (6)	0.0013 (5)	0.0027 (4)	0.0007 (5)
C16	0.0241 (6)	0.0269 (6)	0.0242 (6)	−0.0028 (5)	0.0017 (4)	−0.0025 (5)
C17	0.0272 (6)	0.0221 (6)	0.0213 (5)	0.0004 (5)	0.0080 (5)	0.0001 (4)
C18	0.0211 (5)	0.0264 (6)	0.0244 (6)	0.0012 (5)	0.0041 (4)	0.0016 (5)
C19	0.0233 (6)	0.0248 (6)	0.0216 (5)	−0.0018 (4)	0.0033 (4)	0.0001 (4)

Geometric parameters (Å, º) top

O1—C1	1.2208 (15)	C9—H9	1.0000
O2—C2	1.2115 (15)	C9—C10	1.5119 (17)
O3—C17	1.3713 (15)	C9—C11	1.5079 (18)
O3—H3	0.92 (2)	C10—H10	1.0000
N1—C1	1.3774 (15)	C10—C11	1.5047 (18)
N1—C2	1.3916 (15)	C11—H11A	0.9900
N1—C12	1.4607 (15)	C11—H11B	0.9900
C1—C3	1.5118 (16)	C12—H12A	0.9900
C2—C4	1.5083 (16)	C12—H12B	0.9900
C3—H3A	1.0000	C12—C13	1.5263 (17)
C3—C4	1.5432 (16)	C13—H13A	0.9900
C3—C8	1.5585 (17)	C13—H13B	0.9900
C4—H4	1.0000	C13—C14	1.5096 (16)
C4—C5	1.5572 (16)	C14—C15	1.3947 (17)
C5—H5	1.0000	C14—C19	1.3929 (17)
C5—C6	1.5041 (16)	C15—H15	0.9500
C5—C10	1.5336 (17)	C15—C16	1.3890 (17)
C6—H6	0.9500	C16—H16	0.9500
C6—C7	1.3275 (17)	C16—C17	1.3907 (17)
C7—H7	0.9500	C17—C18	1.3891 (17)
C7—C8	1.5042 (17)	C18—H18	0.9500
C8—H8	1.0000	C18—C19	1.3857 (17)
C8—C9	1.5333 (17)	C19—H19	0.9500

C17—O3—H3	107.2 (15)	C11—C9—H9	117.0
C1—N1—C2	112.97 (10)	C11—C9—C10	59.77 (8)
C1—N1—C12	124.18 (10)	C5—C10—H10	116.7
C2—N1—C12	122.81 (10)	C9—C10—C5	110.48 (10)
O1—C1—N1	123.86 (11)	C9—C10—H10	116.7
O1—C1—C3	127.16 (11)	C11—C10—C5	122.63 (10)
N1—C1—C3	108.98 (10)	C11—C10—C9	59.98 (8)
O2—C2—N1	123.37 (11)	C11—C10—H10	116.7
O2—C2—C4	127.95 (11)	C9—C11—H11A	117.7
N1—C2—C4	108.67 (10)	C9—C11—H11B	117.7
C1—C3—H3A	110.3	C10—C11—C9	60.25 (8)
C1—C3—C4	104.61 (9)	C10—C11—H11A	117.7
C1—C3—C8	111.96 (10)	C10—C11—H11B	117.7
C4—C3—H3A	110.3	H11A—C11—H11B	114.9
C4—C3—C8	109.35 (9)	N1—C12—H12A	109.1
C8—C3—H3A	110.3	N1—C12—H12B	109.1
C2—C4—C3	104.76 (9)	N1—C12—C13	112.65 (10)
C2—C4—H4	110.3	H12A—C12—H12B	107.8
C2—C4—C5	111.57 (10)	C13—C12—H12A	109.1
C3—C4—H4	110.3	C13—C12—H12B	109.1
C3—C4—C5	109.58 (9)	C12—C13—H13A	109.6
C5—C4—H4	110.3	C12—C13—H13B	109.6
C4—C5—H5	111.6	H13A—C13—H13B	108.2
C6—C5—C4	106.92 (9)	C14—C13—C12	110.09 (10)
C6—C5—H5	111.6	C14—C13—H13A	109.6
C6—C5—C10	110.41 (10)	C14—C13—H13B	109.6
C10—C5—C4	104.31 (9)	C15—C14—C13	122.11 (11)
C10—C5—H5	111.6	C19—C14—C13	119.93 (11)
C5—C6—H6	122.7	C19—C14—C15	117.88 (11)
C7—C6—C5	114.68 (11)	C14—C15—H15	119.4
C7—C6—H6	122.7	C16—C15—C14	121.23 (11)
C6—C7—H7	122.7	C16—C15—H15	119.4
C6—C7—C8	114.59 (11)	C15—C16—H16	120.1
C8—C7—H7	122.7	C15—C16—C17	119.86 (11)
C3—C8—H8	111.6	C17—C16—H16	120.1
C7—C8—C3	106.99 (10)	O3—C17—C16	118.25 (11)
C7—C8—H8	111.6	O3—C17—C18	122.08 (11)
C7—C8—C9	110.59 (10)	C18—C17—C16	119.66 (11)
C9—C8—C3	104.27 (10)	C17—C18—H18	120.1
C9—C8—H8	111.6	C19—C18—C17	119.81 (11)
C8—C9—H9	117.0	C19—C18—H18	120.1
C10—C9—C8	110.33 (10)	C14—C19—H19	119.2
C10—C9—H9	117.0	C18—C19—C14	121.51 (11)
C11—C9—C8	121.86 (11)	C18—C19—H19	119.2

O1—C1—C3—C4	−178.30 (11)	C5—C6—C7—C8	−0.72 (16)
O1—C1—C3—C8	−59.98 (15)	C5—C10—C11—C9	96.31 (12)
O2—C2—C4—C3	178.33 (12)	C6—C5—C10—C9	52.63 (13)
O2—C2—C4—C5	59.86 (16)	C6—C5—C10—C11	−14.10 (16)
O3—C17—C18—C19	177.36 (10)	C6—C7—C8—C3	−58.08 (14)
N1—C1—C3—C4	0.97 (12)	C6—C7—C8—C9	54.89 (14)
N1—C1—C3—C8	119.29 (10)	C7—C8—C9—C10	−51.60 (13)
N1—C2—C4—C3	−0.39 (12)	C7—C8—C9—C11	14.71 (16)
N1—C2—C4—C5	−118.87 (10)	C8—C3—C4—C2	−120.42 (10)
N1—C12—C13—C14	−176.50 (10)	C8—C3—C4—C5	−0.61 (12)
C1—N1—C2—O2	−177.71 (11)	C8—C9—C10—C5	−0.86 (14)
C1—N1—C2—C4	1.08 (13)	C8—C9—C10—C11	115.82 (12)
C1—N1—C12—C13	97.13 (13)	C8—C9—C11—C10	−96.40 (12)
C1—C3—C4—C2	−0.34 (12)	C10—C5—C6—C7	−54.04 (14)
C1—C3—C4—C5	119.47 (10)	C11—C9—C10—C5	−116.68 (11)
C1—C3—C8—C7	−59.82 (12)	C12—N1—C1—O1	0.18 (18)
C1—C3—C8—C9	−177.03 (9)	C12—N1—C1—C3	−179.12 (10)
C2—N1—C1—O1	177.99 (11)	C12—N1—C2—O2	0.13 (19)
C2—N1—C1—C3	−1.31 (13)	C12—N1—C2—C4	178.92 (10)
C2—N1—C12—C13	−80.46 (14)	C12—C13—C14—C15	−92.81 (13)
C2—C4—C5—C6	60.69 (12)	C12—C13—C14—C19	83.66 (13)
C2—C4—C5—C10	177.68 (9)	C13—C14—C15—C16	175.06 (11)
C3—C4—C5—C6	−54.85 (12)	C13—C14—C19—C18	−175.00 (11)
C3—C4—C5—C10	62.13 (11)	C14—C15—C16—C17	−0.43 (18)
C3—C8—C9—C10	63.09 (12)	C15—C14—C19—C18	1.62 (17)
C3—C8—C9—C11	129.40 (12)	C15—C16—C17—O3	−177.24 (10)
C4—C3—C8—C7	55.64 (12)	C15—C16—C17—C18	2.23 (18)
C4—C3—C8—C9	−61.57 (11)	C16—C17—C18—C19	−2.10 (18)
C4—C5—C6—C7	58.84 (14)	C17—C18—C19—C14	0.15 (18)
C4—C5—C10—C9	−61.91 (12)	C19—C14—C15—C16	−1.48 (18)
C4—C5—C10—C11	−128.65 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.92 (2)	1.98 (2)	2.8955 (13)	172 (2)
C13—H13A···O2ⁱⁱ	0.99	2.52	3.4396 (16)	154
C6—H6···O1ⁱⁱⁱ	0.95	2.50	3.4473 (15)	176

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y, z; (iii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We are grateful to GVSU's Weldon Fund for financial support of this work. We thank Dr Randy Winchester (GVSU) for sharing these experiments with the Fall 2023 CHM 480 course and Dr Matt Hart (GVSU) for use of the amine starting materials.

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research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Syntheses and crystal structures of the imides 4-(2-phenyl­eth­yl)- and 4-[2-(4-hy­dr­oxy­phen­yl)eth­yl]-4-aza­tetra­cyclo­[5.3.2.02,6.08,10]dodec-11-ene-3,5-dione

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

References

research communications

Syntheses and crystal structures of the imides 4-(2-phenylethyl)- and 4-[2-(4-hydroxyphenyl)ethyl]-4-azatetracyclo[5.3.2.0^2,6.0^8,10]dodec-11-ene-3,5-dione

3. Supramolecular features