Crystal structures of five new substituted tetra­hydro-1-benzazepines with potential anti­parasitic activity

Macías, M.A.; Acosta, L.M.; Sanabria, C.M.; Palma, A.; Roussel, P.; Gauthier, G.H.; Suescun, L.

doi:10.1107/S2053229616004885

Crystal structures of five new substituted tetrahydro-1-benzazepines with potential antiparasitic activity

M. A. Macías, L. M. Acosta, C. M. Sanabria, A. Palma, P. Roussel, G. H. Gauthier and L. Suescun

Tetrahydro-1-benzazepines have been described as potential antiparasitic drugs for the treatment of chagas disease and leishmaniasis, two of the most important so-called `forgotten tropical diseases' affecting South and Central America, caused by Trypanosoma cruzi and Leishmania chagasi parasites, respectively. Continuing our extensive work describing the structural characteristics of some related compounds with interesting biological properties, the crystallographic features of three epoxy-1-benzazepines, namely (2SR,4RS)-6,8-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (1), (2SR,4RS)-6,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (2), and (2SR,4RS)-8,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (3), all C₂₂H₂₁NO, and two 1-benzazepin-4-ols, namely 7-fluoro-cis-2-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol, C₁₈H₁₈FNO, (4), and 7-fluoro-cis-2-[(E)-pent-1-enyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol, C₁₅H₂₀FNO, (5), are described. Some peculiarities in the crystallization behaviour were found, involving significant variations in the crystalline structures as a result of modest changes in the peripheral substituents in (1)-(3) and the occurrence of discrete disorder due to the molecular overlay of enantiomers with more than one conformation in (5). In particular, an interesting phase change on cooling was observed for compound (5), accompanied by an approximate fourfold increase of the unit-cell volume and a change of the Z' value from 1 to 4. This transition is a consequence of the partial ordering of the pentenyl chains in half of the molecules breaking half of the $\overline{3}$ symmetry axes observed in the room-temperature structure of (5). The structural assembly in all the title compounds is characterized by not only (N,O)-H

(O,N) hydrogen bonds, but also by unconventional C-H

O contacts, resulting in a wide diversity of packing.

Keywords: benzazepine derivatives; reaction pathway; antiparasitic activity; phase transition; discrete disorder; crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616004885/wq3111sup1.cif Contains datablocks Compound_1, Compound_2, Compound_3, Compound_4, Compound_5a, Compound_5b
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_1sup2.hkl Contains datablock Compound_1
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_2sup3.hkl Contains datablock Compound_2
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_3sup4.hkl Contains datablock Compound_3
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_4sup5.hkl Contains datablock Compound_4
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_5asup6.hkl Contains datablock Compound_5a
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616004885/wq3111Compound_5bsup7.hkl Contains datablock Compound_5b
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616004885/wq3111sup8.pdf Figure showing the conformers of (5LT)

CCDC references: 1470211; 1470210; 1470209; 1470208; 1470207; 1470206

Introduction top

\ Tetrahydro-1-benzazepines have been described as potential antiparasitic drugs for the treatment of chagas disease and leishmaniasis, two of the most important, so-called `forgotten tropical diseases' affecting South and Central America, caused by Trypanosoma cruzi and Leishmania chagasi parasites, respectively (Gómez-Ayala et al., 2010). A simple synthetic approach for the stereoselective synthesis of exo-2-aryl-1,4-epoxytetrahydro-1-benzazepines and the alcohol derivatives exo-2-aryl-1,4-tetrahydro-1-benzazepine-4-ols, through the selective oxidation of substituted ortho-allyl-N-benzylanilines and subsequent intramolecular 1,3-dipolar cycloaddition of the formed nitrones and posterior opening of the epoxide, was described (Gómez-Ayala et al., 2006; Acosta, Palma & Bahsas, 2010; Acosta et al., 2012) and systematically applied to prepare new compounds in the search for molecules with better biological activity against these parasites. Part of this systematic study of particularly active molecules (Acosta et al., 2009; Acosta et al., 2008; Acosta, Palma, Bahsas et al., 2010; Gómez et al., 2008, 2009, 2010, 2011; Sanabria et al., 2010; Blanco et al., 2012a,b,c; Yépes et al., 2012, 2013; Guerrero et al., 2014; Sanabría et al., 2014) included the crystal structure determination. Two series of structures are presented and their conformation and packing are described and compared in this paper: (2SR,4RS)-6,8-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-\ 1H-1,4-epoxy-1-benzazepine, (1), (2SR,4RS)-6,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-\ 1H-1,4-epoxy-1-benzazepine, (2), (2SR,4RS)-8,9-dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-\ 1H-1,4-epoxy-1-benzazepine, (3), are epoxy-1-benzazepines differing only in the position of two methyl groups in the 6-, 8- and 9-positions in the fused benzene ring, and 7-fluoro-cis-2-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1-\ benzazepin-4-ol, (4), and 7-fluoro-cis-2-[(E)-pent-1-enyl]-2,3,4,5-tetrahydro-1H-\ 1-benzazepin-4-ol, (5), are 1-benzazepin-4-ols replacing both methyl residues for fluorine at the 7-position 7, differing in the residues at the 2-position.

Experimental top

Synthesis and crystallization top

The syntheses of the compounds (1)–(5) were carried out following our previously estabished experimental conditions (Acosta, Palma & Bahsas, 2010; Acosta et al., 2012). Particular details are described as follows. Recrystallization of (1)–(3) by slow evaporation of a solution in heptane gave crystals of suitable size and quality for single-crystal X-ray diffraction. In the case of compounds (4) and (5), the recrystallization was performed from a heptane–ethyl acetate (1:1 v/v) mixture which also gave crystals suitable for single-crystal X-ray diffraction.

Compounds (1)–(3) top

Sodium tungstate dihydrate, Na₂WO₄·2H₂O (7 mol%), followed by 30% aqueous hydrogen peroxide solution (0.30 mol), were added to a stirred and cooled (273 K) solution of the appropriate dimethyl-substituted 2-allyl-N-(naphthalen-1-ylmethyl)aniline (0.10 mol) in methanol (20 ml). The resulting mixtures were then stirred at ambient temperature for 72 h. Each mixture was filtered and the solvent removed under reduced pressure. Toluene (30 ml) was added to the solid residue and the resulting solution was heated under reflux for 18 h. After cooling each solution to ambient temperature, the solvent was removed under reduced pressure and the crude product was purified by chromatography on silica using heptane–ethyl acetate (compositions ranged from 60:1 to 10:1 v/v) as eluent to give compounds (1)–(3) with yields of 69, 67 and 59%, respectively (see Scheme 1).

Compounds (4) and (5) top

To stirred and ice-bath-cooled methanolic solutions of the 1,4-epoxy cycloadducts were added zinc powder (10 mmol), glacial acetic acid (7 mmol) and hydrochloric acid (7 mmol, 37% HCl). The resulting mixtures were stirred at 273 K for an additional 30 min and the crude products were filtered. Each filtrate was then basified with 25% aqueous NH₄OH to pH 8, extracted with EtOAc (3 × 50 ml), and the combined organic layers were dried over anhydrous Na₂SO₄. The solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, heptane–EtOAc, 10:1 to 1:1 v/v) to give the compounds (4) and (5) with yields of 93 and 90%, respectively (see Scheme 2).

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were placed in calculated positions (C—H = 0.93–1.00 Å) and included as riding contributions with isotropic displacement parameters set at 1.2-1.5 times of the U_eq value of the parent atom. H atoms belonging to OH and NH groups were located in difference density maps and refined freely. Some low-angle reflections strongly affected by the experiment, attenuated by the beam stop, for instance, were omitted for the final refinements, viz. for (1) 366 and 366, for (2) 011 and for (5) 120.

Results and discussion top

The two groups of compounds described show different conformational and packing characteristics due to the size and position of substituents and the different conformations of the benzodiazepine nucleus (rigid in the epoxides and more flexible in the alcohols).

Three structural isomers of naphthalen-1-yl-substituted tetrahydro-1-benzazepines with interesting crystallization behaviour top

The non-enantioselective synthesis pathway (Gómez-Ayala et al., 2010; Acosta, Palma & Bahsas, 2010; OR Acosta, Palma, Bahsas et al., 2010) that produce racemic mixtures of the structural isomers (1), (2) and (3), however, they crystallize in different forms. Compound (1) crystallizes as a racemate in the space group P2₁/c, with Z' = 2, where the two molecules in the asymmetric unit were selected to have the same absolute configuration [(2S, 4R), as shown in Fig. 1]. Compund (2) crystallizes in the Schonke space group P2₁2₁2₁, selecting the same (2S,4R) absolute configuration for the refinement (Fig. 2a), and compound (3) crystallizes in the Sohncke space group P2₁ and the crystal selected for structure determination was the (2S, 4R) enantiomer (Fig. 2b). This crystallization behaviour of slightly different isomers in different space groups with different crystalline symmetries has been described previously for this kind of compound (Acosta et al., 2008; Acosta, Palma, Bahsas et al., 2010).

The A conformer in (1) is conformationally identical to molecules (2) and (3), since the epoxybenzazepine nucleus is rather rigid, as shown by the overlay of the nuclei of (1A) and (2) with (3) (atoms N1, O1, C2, C3, C4, C5, C5A, C6, C7, C8, C9 and C9A), that give r.m.s. deviations of 0.0345 and 0.0249 Å, respectively. The dihedral angle between the naphthyl and benzyl rings are 88.14 (6), 87.66 (9) and 85.74 (6)° in (1A), (2) and (3), respectively, which indicates that the orthogonal conformation of the rings is the most stable for these molecules. Considering the conformation of the fused rings in the nuclei of the molecules (1A), (2) and (3), the five- (O1/N1/C2–C4) and six-membered (O1/N1/C9A/C5A/C5/C4) rings adopt an intermediate conformation between half-chair and envelope (Table 2) (Cremer & Pople, 1975).

The (1B) conformer in (1) shows a similar but not identical conformation of the epoxybenzazepine nucleus with respect to (1A) [r.m.s. deviation = 0.045 Å, larger than that of (1A) and (2) with (3)] with slightly different puckering parameters for the five- and six-memebred rings than those observed between (1A), (2) and (3) (Table 2). The main difference between (1B) and the other molecules is the dihedral angle between the naphthyl and benzyl rings of 4.26 (6)°, indicating that both rings are almost parallel and that molecule (1B) shows a relatively planar arrangement.

Even though the three compounds show different space groups, a motif of intermolecular interactions seems to be common to the three structures that form chains of molecules related by a 2₁ screw axis in the three cases along b. In the three compunds, weak C—H···O and C—H···π interactions direct the formation of chains (Tables 3, 4 and 5). In (1A), one C2A—H2A···O1Aⁱ [symmetry code: (i) -x+1, y+1/2] and one C5A—H5AA···Cg_1A2ⁱⁱ [Cg_1A2 is the centroid of the C20A–C24A/C29A ring; symmetry code: (ii) -x+1, y-1/2, -z+1/2] interaction connect molecules related by a 2₁ screw axis (Fig. 3a), in (2), only one weak C82—H82···O1ⁱ [symmetry code: (i) -x+1, y+1/2, ???] hydrogen bond connects consecutive molecules (Fig. 3b), and in (3), one C8—H8···O1ⁱⁱⁱ [symmetry code: (iii) x, y+1, z] and two C27—H27···Cg₃₁^iv and C28—H28···Cg₃₂^iv [Cg₃₁ and Cg₃₂ are the centroids of the C20–C24/C29 and C24–C29 rings, respectively; symmetry code: (iv) -x, y+1/2, -z+1] connect consecutive molecules (Fig. 3c), with additional C—H···π or van der Waals interactions connecting parallel chains. The case of compound (1) is more complex, though, since the crystal is centrosymmetric, therefore inverted chains of (1A) (2R,4S) enantiomers also run parallel to the b axis; furthermore, molecule (1B), with a different conformation, is also present. It is interesting, however, that molecules (1A) pack in separate layers from (1B) which form inversion dimers through C4B—H4B···O1B^v [symmetry code: (v) -x+2, -y, -z+1] and each molecule stacks with another inverted molecule along b (Fig. 3a). Chains of dimers, related by the c-glide plane have an parallel disposition of the planar benzyl and naphthyl ring that allows for C—H···π interactions.

Two new examples in the tetrahydro-1-benzazepine series: occurrence of discrete disorder top

Compounds (4) and (5) crystallize as racemates in the centrosymmetric Pbca and R3 space groups, respectively; both compounds were studied at room temperature and at 100 K. Compound (4) shows the same structure at both temperatures, but compound (5) shows a phase transition between room temperature, i.e. compound (5RT), and 100 K, i.e. compound (5LT), as will be described below.

For both compounds, the seven-membered ring adopts a chair conformation (Table 2) with the hydroxy, and styryl/pentenyl substituents [in (4) and (5)] in equatorial positions and the fluorobenzyl ring in a bisectional conformation, as shown in Fig. 4. Even though the seven-memebered ring of the tetrahydrobenzazepine nucleus has conformational freedom, all the independent molecules in (4), (5RT) and (5LT) show a very consistent conformation, with a maximum average r.m.s. deviation of 0.0794 Å of the common 7-fluorotetrahydrobenzazepine nucleus (atoms N1, O1, C2, C3, C4, C5, C52, C6, C7, C8, C9 and C92) between the molecule in (4) and molecule 3 of (5LT).

In the molecule of (4), the C22–C28 plane containing the styryl group is oriented towards the 7-fluorotetrahydrobenzazepine nucleus, making a dihedral angle of 60.99 (5)° (Fig. 4a). This general conformation is conserved at room temperature and 100 K. In this molecule, the styryl group is not completely planar since the C24—C23—C22—C21 torsion angle, which has a value of 168.68 (13)°, is slightly distorted considering that only Csp² atoms are involved. The heterocyclic ring (atoms N1/C2–C5/C5A/C9A) in both compounds has similar puckering parameters values (Table 2) (Cremer & Pople, 1975).

Atoms of the pentenyl chain of the room-temperature structure of compound (5), denoted (5RT), exhibited high anisotropic displacement ellipsoids in the initial refinement cycles consistent with positional disorder in two different conformations of the same chain, slightly rotated along the C2—C10 bond, and were modelled as such (Fig. 4b). This positional disorder turned out to be very important when a new data collection was performed at 100 K, denoted (5LT), where it was observed that this disorder would correspond to the co-existence of various possible conformations of the pentenyl residue (Fig. 4c). The disorder in the room-temperature structure was refined successfully assuming two pentenyl chains in the same conformation with refined occupancies of 48.3 (5) and 51.7 (5)%, and an average C11—C12—C13—C14 torsion angle of -167.9° (Fig. 4b). However, the data at 100 K revealed that in fact it is possible to differentiate a new conformation as result of a rotation in the C12—C13 bond giving rise to a structure with a Z' value of 4. The four independent molecules in the asymmetric unit, each with different degree of disorder, are the result of the averaging of different proportions of two main different conformation of the pentenyl chain [with one of the conformations showing two possible torsion angles as in (5RT)]. In this sense, molecules 1 (2R,4S) and 2 (2S,4R) (see Fig. 4c) correspond to two ordered conformers, with torsion angles (C111—C112—C113—C114 and C211—C212—C213—C214) of -179.22 (14) and 72.11 (16)°, respectively (called conformers α and β in Fig. S1 of the Supporting information). Molecule 3 (2S,4R) shows disorder, similar to that of (5RT), successfully described as the co-existence of two chains with the same α conformation but in slightly different positions, with occupancies of 84.1 (2) and 15.9 (2)% and torsion angles of 176.06 (19) and 174.5 (11)°. Molecule 4 (2S,4R) represents a mixture of both α and β conformers, with two orientations of the former, with occupancies of 31.9 (8) and 34.0 (8)%, and an average torsion angle of ~176.5°, and a third one corresponding to the β conformer having an occupancy of 34.2 (3) and a torsion angle of 71.5 (6)° (see Fig. S1 in the Supporting information). The molecular connectivity in (5) (Tables 6 and 7) is quite different from that in (4). At room temperature, six molecules are connected by N1—H1N···O1ⁱ [symmetry code: (i) x-y+2/3, x+1/3, -z+4/3] [not in Table 6, but in Table 8 for compound (4)?] hydrogen bonds in a racemic ring parallel to (001), leaving the pentenyl substituents oriented to the centre and the F atoms oriented outward, describing a threefold rotoinversion axis with [001] direction (Fig. 5a). Each six-membered ring is connected to six other equivalent structures along the three dimensions connected by six pairs of N1—H1N···O1ⁱ and O1—H1O···N1ⁱⁱ [symmetry code: (ii) -y+2/3, x-y+1/3, z+1/3] [not in Table 6, but in Table 8 for compound (4)?] hydrogen bonds generating R₄⁴(8) motifs (Fig. 5b). Each pair of enantiomers are also related by an inversion centre at (1/2, 1/2, 1/2) and connected between them by probably induced dipolar interactions involving the halogen substituent. In a supramolecular perspective, a view along [001] allows one to differentiate the centre of the rings at (2/3, 1/3, z) and (1/3, 2/3, z) (Fig. 5a). The structure at 100 K is transformed in a superstructure of the crystal structure at room temperature since the conformers (see Fig. S1 in the Supporting information) are perceptibly different. In this case, the molecular connectivity remains as room temperature and each individual molecule in the asymmetric unit constitutes a racemic sixfold molecular ring by N(1,2,3,4)1—H(1,2,3,4)N···O(3ⁱ,1ⁱⁱ,2ⁱⁱⁱ,4^iv)1 [symmetry codes: (i) x, y, z+1; (ii) -y+2/3, x-y+1/3, z-2/3; (iii) x-y+2/3, x+1/3, -z+1/3; (iv) y-1/3, -x+y+1/3, -z+4/3] hydrogen bonds (Table 7). However, the presence of both α and β conformers break half of the threefold rotoinversion axes observed at room temperature leaving a threefold screw axis with [001] direction in the centre of each molecular ring (Fig. 5c).

The supramolecular assembly of both molecules in their crystals differ significantly, as expected for the very different sizes of the styryl and pentenyl substituents. In compound (4), each molecule is connected to four equivalent molecules at the same z value by two pairs of N1—H1N···O1ⁱ and O1—H1O···N1ⁱⁱ [symmetry codes: (i) x, y-1, z; (ii) -x+3/2, y+1/2, z] hydrogen bonds (Table 8), where atoms N1 and O1 act each as donor and acceptor. Hydrogen-bonded molecules form enantiomorphic chains along the [010] direction (Fig. 6). The chains have a polar disposition, since all molecules in a chain are related by the b-glide plane normal to a (Fig. 6a). This makes the F atoms from all the molecules lie on the same side of the chain, leaving all nonpolar moieties on the other side. Each chain connects with an inverted chain on the [001] direction through weak C6—H6···F1ⁱⁱⁱ [symmetry code: (iii) -x+1, -y+1, -z+1] dipolar interactions (2.47 Å) (Jelsch et al., 2015) (Figs. 6b and 6c). The interactions among double chains in the [100] and [001] directions are weak and probably dipolar or van der Waals in nature since no weak hydrogen bonds or π–π stacking interactions are detected.

Compund (5) shows different structures at room temperature and 100 K, with the low-temperature structure crystallizing in a klassengleiche subgroup of the room-temperature one, with a quadrupling of the unit-cell volume in the (110) plane. The descriptions of (5LT) could be obtained from that of (5RT) by the matrix P = [200 220 001] (International Tables for Crystallography, 2011). In order to confirm the group/subgroup relation of both structures and determine the degree of distortion of one respect to the other, the ordered part of the molecule in the (5RT) crystal was transformed into the subgroup of (5LT) using TRANSTRU program in the Bilbao Crystallography Server (Aroyo, Kirov et al., 2006; Aroyo, Perez-Mato et al., 2006; Aroyo et al., 2011) and the output structure, consisting of the ordered nuclei of the molecules was compared with the same nuclei in the (5LT) structure (all pentenyl residues, ordered and disordered, were removed) using COMPSTRU (Tasci et al., 2012) and an almost perfect overlap was obtained with an average/maximum atom displacement of 0.1667/0.2539 Å (for atom F1A). These deviations are very small considering the temperature difference and the fact that the room-temperature structure shows one molecule with the pentenyl chain split in two main positions, while the 100 K structure shows four independent molecules, two of them ordered and the other two displaying two and three different pentenyl chain conformations. This strongly suggests that the phase transition observed between room temperature and 100 K could be entirely explained by the partial ordering of the pentenly chains in half of the molecules, that breaks half of the 3 symmetry axes of the room-temperature structure on cooling. The refinement of the 100 K structure using the room-temperature model (R3 space group with halved a and b unit-cell parameters) using hkl data transformed using the inverse of the matrix above, provides a reasonable but significantly poorer model, with unreasonable displacement parameters (too high for a low-temperature model), a higher R factor and a much larger degree of disorder of the pentenyl chain that is very hard to model with less than three separate conformations. This clearly justifies the use of the subgroup to model the 100 K structure and again confirm that the ordering of the pentenyl chains is key to this phase transition.

Structure description top

Synthesis and crystallization top

Refinement details top

Computing details top

For all compounds, data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for Compound_1, Compound_2, Compound_4; SUPERFLIP (Palatinus & Chapuis, 2007) for Compound_3, Compound_5a, Compound_5b. Program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) for Compound_1, Compound_3, Compound_4, Compound_5a, Compound_5b; SHELXL2014 (Sheldrick, 2008a, 2015b) for Compound_2. For all compounds, molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures top

	Fig. 1. The two independent molecules of compound (1), both shown as the (2S,4R) enantiomorph. The molecular structures show displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The molecular structure of (a) compound (2) and (b) compound (3), showing displacement ellipsoids drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. The crystal structures of (a) compound (1), (b) compound (2) and (c) compound (3), showing the formation of hydrogen-bonded chains along the [010] direction.
	Fig. 4. The molecular structures of (a) compound (4), (b) compound (5) at room temperature and (c) compound (5) at 100 K with Z' = 4, showing displacement ellipsoids drawn at the 50% probability level.
	Fig. 5. (a) The packing of compound (5) at room temperature, showing the molecular rings with threefold rotoinvertion symmetry. (b) Compound (5) at room temperature, showing the R₄⁴(8) motifs. (c) The packing of compound (5) at 100 K, shown as the superstructure of the crystal structure at room temperature.
	Fig. 6. (a) The packing of the compound (4). Views along (b) [100] and (c) [010], showing the (N,O)—H···(O,N) and C—H···F hydrogen bonds.

(Compound_1) (2SR,4RS)-6,8-Dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine top

Crystal data top

C₂₂H₂₁NO	F(000) = 1344
M_r = 315.40	D_x = 1.300 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.8049 (10) Å	Cell parameters from 9740 reflections
b = 10.7126 (5) Å	θ = 2.5–27.4°
c = 12.1932 (4) Å	µ = 0.08 mm⁻¹
β = 95.929 (1)°	T = 100 K
V = 3222.7 (2) Å³	Parallelipiped, less
Z = 8	0.45 × 0.35 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	6012 reflections with I > 2σ(I)
π and ω scans	R_int = 0.040
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 27.5°, θ_min = 2.1°
T_min = 0.640, T_max = 0.746	h = −32→29
48596 measured reflections	k = −12→13
7121 independent reflections	l = −11→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0523P)² + 2.1093P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
7121 reflections	Δρ_max = 0.37 e Å⁻³
437 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₂H₂₁NO	V = 3222.7 (2) Å³
M_r = 315.40	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 24.8049 (10) Å	µ = 0.08 mm⁻¹
b = 10.7126 (5) Å	T = 100 K
c = 12.1932 (4) Å	0.45 × 0.35 × 0.20 mm
β = 95.929 (1)°

Data collection top

Bruker Kappa APEXII diffractometer	7121 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	6012 reflections with I > 2σ(I)
T_min = 0.640, T_max = 0.746	R_int = 0.040
48596 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.37 e Å⁻³
7121 reflections	Δρ_min = −0.26 e Å⁻³
437 parameters

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
C28B	0.90602 (6)	0.47577 (14)	0.66839 (12)	0.0197 (3)
H28B	0.9428	0.4893	0.6563	0.024*
C21B	0.86514 (6)	0.22394 (14)	0.46455 (12)	0.0209 (3)
H21B	0.8796	0.1749	0.4096	0.025*
C22B	0.81091 (6)	0.20496 (15)	0.48594 (12)	0.0235 (3)
H22B	0.7895	0.1438	0.4453	0.028*
C23B	0.78897 (6)	0.27362 (15)	0.56446 (12)	0.0219 (3)
H23B	0.7524	0.2600	0.5782	0.026*
C27B	0.88377 (6)	0.54502 (15)	0.74688 (12)	0.0230 (3)
H27B	0.9051	0.6056	0.7883	0.028*
C26B	0.82940 (6)	0.52654 (15)	0.76618 (12)	0.0239 (3)
H26B	0.8141	0.5750	0.8204	0.029*
C25B	0.79852 (6)	0.43897 (15)	0.70720 (12)	0.0224 (3)
H25B	0.7619	0.4271	0.7209	0.027*
C24B	0.82058 (6)	0.36549 (14)	0.62571 (11)	0.0193 (3)
C29B	0.87542 (6)	0.38444 (13)	0.60482 (11)	0.0178 (3)
C20B	0.89752 (6)	0.31156 (13)	0.52118 (11)	0.0172 (3)
C21A	0.40742 (6)	0.75903 (14)	0.28172 (11)	0.0183 (3)
H21A	0.4300	0.7129	0.3349	0.022*
C22A	0.35143 (6)	0.76661 (14)	0.29133 (12)	0.0200 (3)
H22A	0.3367	0.7245	0.3500	0.024*
C23A	0.31807 (6)	0.83392 (14)	0.21706 (12)	0.0190 (3)
H23A	0.2804	0.8390	0.2247	0.023*
C24A	0.33970 (6)	0.89639 (13)	0.12832 (11)	0.0171 (3)
C25A	0.30620 (6)	0.96909 (14)	0.05136 (12)	0.0201 (3)
H25A	0.2686	0.9765	0.0592	0.024*
C26A	0.32723 (6)	1.02862 (14)	−0.03388 (12)	0.0219 (3)
H26A	0.3043	1.0771	−0.0845	0.026*
C27A	0.38279 (6)	1.01832 (14)	−0.04672 (12)	0.0208 (3)
H27A	0.3971	1.0590	−0.1066	0.025*
C28A	0.41652 (6)	0.94975 (14)	0.02680 (11)	0.0179 (3)
H28A	0.4540	0.9440	0.0173	0.021*
C29A	0.39618 (6)	0.88722 (13)	0.11701 (11)	0.0158 (3)
C20A	0.43018 (6)	0.81698 (13)	0.19693 (11)	0.0158 (3)
N1A	0.52000 (5)	0.75543 (11)	0.28857 (9)	0.0164 (3)
O1A	0.51701 (4)	0.62248 (9)	0.26606 (8)	0.0186 (2)
C2A	0.49058 (6)	0.80977 (13)	0.18739 (11)	0.0157 (3)
H2A	0.5048	0.8954	0.1751	0.019*
C3A	0.50543 (6)	0.72134 (14)	0.09308 (11)	0.0185 (3)
H3AA	0.4725	0.6922	0.0474	0.022*
H3AB	0.5296	0.7636	0.0451	0.022*
C4A	0.53460 (6)	0.61237 (14)	0.15643 (11)	0.0190 (3)
H4A	0.5226	0.5309	0.1220	0.023*
C5A	0.59618 (6)	0.62154 (14)	0.16806 (11)	0.0190 (3)
H5AA	0.6121	0.5416	0.1965	0.023*
H5AB	0.6089	0.6374	0.0949	0.023*
C6A	0.66938 (6)	0.76068 (14)	0.26448 (11)	0.0185 (3)
C7A	0.68360 (6)	0.86332 (15)	0.33189 (12)	0.0207 (3)
H7A	0.7207	0.8867	0.3444	0.025*
C8A	0.64515 (6)	0.93285 (14)	0.38160 (11)	0.0199 (3)
C9A	0.59144 (6)	0.89464 (14)	0.36574 (11)	0.0184 (3)
H9A	0.5646	0.9391	0.4001	0.022*
N1B	0.99146 (5)	0.27205 (11)	0.59408 (9)	0.0168 (3)
O1B	0.99060 (4)	0.14348 (9)	0.55752 (8)	0.0201 (2)
C2B	0.95622 (6)	0.33158 (13)	0.50117 (11)	0.0167 (3)
H2B	0.9640	0.4231	0.4996	0.020*
C3B	0.97530 (6)	0.26920 (14)	0.39758 (11)	0.0187 (3)
H3BA	0.9441	0.2473	0.3437	0.022*
H3BB	1.0001	0.3246	0.3615	0.022*
C4B	1.00495 (6)	0.15132 (14)	0.44408 (11)	0.0203 (3)
H4B	0.9923	0.0757	0.4008	0.024*
C5B	1.06598 (6)	0.16314 (15)	0.45203 (12)	0.0221 (3)
H5BA	1.0773	0.1847	0.3789	0.027*
H5BB	1.0829	0.0826	0.4756	0.027*
C6B	1.13816 (6)	0.30607 (15)	0.54831 (12)	0.0227 (3)
C7B	1.15254 (6)	0.40022 (16)	0.62457 (12)	0.0242 (3)
H7B	1.1890	0.4285	0.6336	0.029*
C8B	1.11508 (6)	0.45440 (15)	0.68815 (12)	0.0227 (3)
C9B	1.06216 (6)	0.41094 (14)	0.67492 (11)	0.0193 (3)
H9B	1.0360	0.4459	0.7177	0.023*
C5A2	0.61473 (6)	0.72585 (14)	0.24602 (11)	0.0170 (3)
C6A2	0.71170 (6)	0.69000 (15)	0.20949 (13)	0.0243 (3)
H6AA	0.7475	0.7256	0.2320	0.036*
H6AB	0.7038	0.6964	0.1293	0.036*
H6AC	0.7113	0.6020	0.2315	0.036*
C8A2	0.66182 (7)	1.04589 (15)	0.45163 (13)	0.0249 (3)
H8AA	0.6303	1.0782	0.4849	0.037*
H8AB	0.6758	1.1106	0.4053	0.037*
H8AC	0.6901	1.0220	0.5099	0.037*
C9A2	0.57655 (6)	0.79158 (14)	0.29984 (11)	0.0166 (3)
C5B2	1.08444 (6)	0.26388 (14)	0.53455 (11)	0.0193 (3)
C6B2	1.17984 (7)	0.25149 (18)	0.48023 (13)	0.0305 (4)
H6BA	1.1802	0.1604	0.4879	0.046*
H6BB	1.2157	0.2848	0.5060	0.046*
H6BC	1.1707	0.2738	0.4026	0.046*
C8B2	1.13274 (7)	0.55414 (16)	0.77154 (13)	0.0310 (4)
H8BA	1.1487	0.6241	0.7344	0.046*
H8BB	1.1597	0.5195	0.8278	0.046*
H8BC	1.1013	0.5836	0.8066	0.046*
C9B2	1.04695 (6)	0.31645 (13)	0.59952 (11)	0.0170 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C28B	0.0206 (7)	0.0186 (8)	0.0196 (7)	0.0005 (6)	0.0012 (5)	0.0010 (5)
C21B	0.0265 (8)	0.0190 (8)	0.0173 (7)	−0.0007 (6)	0.0023 (6)	−0.0015 (5)
C22B	0.0253 (8)	0.0220 (8)	0.0224 (7)	−0.0053 (6)	−0.0018 (6)	−0.0007 (6)
C23B	0.0196 (7)	0.0234 (8)	0.0224 (7)	−0.0019 (6)	0.0008 (6)	0.0036 (6)
C27B	0.0290 (8)	0.0201 (8)	0.0196 (7)	0.0013 (6)	0.0001 (6)	−0.0027 (6)
C26B	0.0297 (8)	0.0230 (8)	0.0191 (7)	0.0072 (6)	0.0033 (6)	−0.0009 (6)
C25B	0.0226 (8)	0.0256 (8)	0.0191 (7)	0.0041 (6)	0.0029 (6)	0.0034 (6)
C24B	0.0219 (7)	0.0184 (7)	0.0170 (6)	0.0022 (6)	−0.0005 (5)	0.0042 (5)
C29B	0.0223 (7)	0.0152 (7)	0.0154 (6)	0.0010 (6)	−0.0002 (5)	0.0036 (5)
C20B	0.0219 (7)	0.0140 (7)	0.0155 (6)	0.0006 (6)	0.0009 (5)	0.0026 (5)
C21A	0.0218 (7)	0.0175 (7)	0.0152 (6)	0.0009 (6)	0.0003 (5)	0.0015 (5)
C22A	0.0234 (8)	0.0199 (8)	0.0174 (7)	−0.0024 (6)	0.0054 (5)	0.0007 (6)
C23A	0.0164 (7)	0.0199 (8)	0.0212 (7)	−0.0011 (6)	0.0044 (5)	−0.0030 (6)
C24A	0.0214 (7)	0.0130 (7)	0.0166 (6)	−0.0008 (5)	0.0004 (5)	−0.0046 (5)
C25A	0.0197 (7)	0.0185 (8)	0.0214 (7)	0.0020 (6)	−0.0007 (5)	−0.0037 (6)
C26A	0.0267 (8)	0.0180 (8)	0.0197 (7)	0.0034 (6)	−0.0044 (6)	0.0004 (6)
C27A	0.0272 (8)	0.0178 (7)	0.0170 (7)	−0.0018 (6)	0.0003 (6)	0.0025 (5)
C28A	0.0200 (7)	0.0171 (7)	0.0164 (6)	−0.0014 (6)	0.0011 (5)	−0.0005 (5)
C29A	0.0204 (7)	0.0125 (7)	0.0141 (6)	−0.0012 (5)	0.0003 (5)	−0.0023 (5)
C20A	0.0197 (7)	0.0133 (7)	0.0142 (6)	−0.0012 (5)	0.0008 (5)	−0.0020 (5)
N1A	0.0197 (6)	0.0146 (6)	0.0147 (5)	0.0001 (5)	−0.0001 (4)	0.0015 (4)
O1A	0.0239 (5)	0.0145 (5)	0.0177 (5)	−0.0011 (4)	0.0031 (4)	0.0021 (4)
C2A	0.0198 (7)	0.0155 (7)	0.0116 (6)	−0.0008 (5)	0.0005 (5)	0.0019 (5)
C3A	0.0198 (7)	0.0212 (8)	0.0144 (6)	0.0018 (6)	0.0012 (5)	−0.0003 (5)
C4A	0.0233 (8)	0.0173 (7)	0.0161 (7)	−0.0004 (6)	0.0015 (5)	−0.0010 (5)
C5A	0.0220 (8)	0.0174 (7)	0.0176 (7)	0.0025 (6)	0.0024 (5)	0.0018 (5)
C6A	0.0200 (7)	0.0190 (7)	0.0166 (6)	0.0017 (6)	0.0014 (5)	0.0076 (5)
C7A	0.0173 (7)	0.0242 (8)	0.0200 (7)	−0.0035 (6)	−0.0006 (5)	0.0067 (6)
C8A	0.0245 (8)	0.0204 (8)	0.0140 (6)	−0.0019 (6)	−0.0011 (5)	0.0034 (5)
C9A	0.0219 (7)	0.0214 (8)	0.0119 (6)	0.0021 (6)	0.0015 (5)	0.0021 (5)
N1B	0.0231 (6)	0.0115 (6)	0.0157 (6)	0.0002 (5)	0.0021 (5)	0.0004 (4)
O1B	0.0302 (6)	0.0125 (5)	0.0182 (5)	−0.0009 (4)	0.0051 (4)	0.0005 (4)
C2B	0.0225 (7)	0.0142 (7)	0.0133 (6)	−0.0005 (6)	0.0006 (5)	0.0010 (5)
C3B	0.0226 (7)	0.0183 (7)	0.0154 (6)	−0.0017 (6)	0.0029 (5)	−0.0009 (5)
C4B	0.0311 (8)	0.0155 (7)	0.0148 (6)	−0.0004 (6)	0.0041 (6)	−0.0027 (5)
C5B	0.0294 (8)	0.0200 (8)	0.0176 (7)	0.0050 (6)	0.0053 (6)	−0.0012 (6)
C6B	0.0239 (8)	0.0275 (9)	0.0166 (7)	0.0028 (6)	0.0022 (6)	0.0088 (6)
C7B	0.0223 (8)	0.0285 (9)	0.0210 (7)	−0.0040 (6)	−0.0024 (6)	0.0085 (6)
C8B	0.0298 (8)	0.0210 (8)	0.0158 (7)	−0.0030 (6)	−0.0044 (6)	0.0054 (6)
C9B	0.0265 (8)	0.0183 (8)	0.0127 (6)	0.0028 (6)	0.0005 (5)	0.0028 (5)
C5A2	0.0203 (7)	0.0174 (7)	0.0132 (6)	0.0009 (6)	0.0011 (5)	0.0050 (5)
C6A2	0.0194 (8)	0.0244 (8)	0.0294 (8)	0.0019 (6)	0.0046 (6)	0.0050 (6)
C8A2	0.0280 (8)	0.0229 (8)	0.0227 (7)	−0.0052 (6)	−0.0023 (6)	0.0008 (6)
C9A2	0.0186 (7)	0.0197 (7)	0.0114 (6)	−0.0003 (6)	−0.0001 (5)	0.0052 (5)
C5B2	0.0251 (8)	0.0184 (8)	0.0144 (6)	0.0023 (6)	0.0019 (5)	0.0039 (5)
C6B2	0.0241 (8)	0.0430 (11)	0.0249 (8)	0.0051 (7)	0.0054 (6)	0.0081 (7)
C8B2	0.0384 (10)	0.0273 (9)	0.0247 (8)	−0.0075 (7)	−0.0091 (7)	0.0005 (7)
C9B2	0.0222 (7)	0.0157 (7)	0.0128 (6)	0.0011 (6)	0.0001 (5)	0.0043 (5)

Geometric parameters (Å, º) top

C28B—C27B	1.371 (2)	C2A—C3A	1.5629 (19)
C28B—C29B	1.419 (2)	C3A—C4A	1.539 (2)
C21B—C20B	1.374 (2)	C4A—C5A	1.523 (2)
C21B—C22B	1.411 (2)	C5A—C5A2	1.508 (2)
C22B—C23B	1.364 (2)	C6A—C7A	1.396 (2)
C23B—C24B	1.421 (2)	C6A—C5A2	1.402 (2)
C27B—C26B	1.407 (2)	C6A—C6A2	1.507 (2)
C26B—C25B	1.367 (2)	C7A—C8A	1.397 (2)
C25B—C24B	1.421 (2)	C8A—C9A	1.388 (2)
C24B—C29B	1.424 (2)	C8A—C8A2	1.514 (2)
C29B—C20B	1.437 (2)	C9A—C9A2	1.393 (2)
C20B—C2B	1.516 (2)	N1B—O1B	1.4471 (15)
C21A—C20A	1.376 (2)	N1B—C9B2	1.4513 (18)
C21A—C22A	1.408 (2)	N1B—C2B	1.4998 (17)
C22A—C23A	1.367 (2)	O1B—C4B	1.4658 (16)
C23A—C24A	1.424 (2)	C2B—C3B	1.5459 (19)
C24A—C25A	1.420 (2)	C3B—C4B	1.540 (2)
C24A—C29A	1.425 (2)	C4B—C5B	1.512 (2)
C25A—C26A	1.368 (2)	C5B—C5B2	1.514 (2)
C26A—C27A	1.407 (2)	C6B—C7B	1.393 (2)
C27A—C28A	1.374 (2)	C6B—C5B2	1.401 (2)
C28A—C29A	1.4240 (19)	C6B—C6B2	1.509 (2)
C29A—C20A	1.4343 (19)	C7B—C8B	1.397 (2)
C20A—C2A	1.517 (2)	C8B—C9B	1.386 (2)
N1A—C9A2	1.4480 (18)	C8B—C8B2	1.508 (2)
N1A—O1A	1.4509 (16)	C9B—C9B2	1.393 (2)
N1A—C2A	1.4858 (16)	C5A2—C9A2	1.397 (2)
O1A—C4A	1.4525 (17)	C5B2—C9B2	1.401 (2)

C27B—C28B—C29B	121.56 (14)	C5A—C4A—C3A	114.40 (12)
C20B—C21B—C22B	121.63 (14)	C5A2—C5A—C4A	110.14 (12)
C23B—C22B—C21B	120.60 (14)	C7A—C6A—C5A2	119.05 (14)
C22B—C23B—C24B	120.24 (14)	C7A—C6A—C6A2	120.83 (13)
C28B—C27B—C26B	120.17 (14)	C5A2—C6A—C6A2	120.10 (14)
C25B—C26B—C27B	120.21 (14)	C6A—C7A—C8A	122.21 (14)
C26B—C25B—C24B	120.84 (14)	C9A—C8A—C7A	118.09 (14)
C25B—C24B—C23B	121.32 (14)	C9A—C8A—C8A2	121.10 (14)
C25B—C24B—C29B	119.34 (14)	C7A—C8A—C8A2	120.80 (14)
C23B—C24B—C29B	119.34 (13)	C8A—C9A—C9A2	120.51 (14)
C28B—C29B—C24B	117.88 (13)	O1B—N1B—C9B2	108.04 (11)
C28B—C29B—C20B	122.73 (13)	O1B—N1B—C2B	100.56 (10)
C24B—C29B—C20B	119.39 (13)	C9B2—N1B—C2B	111.79 (11)
C21B—C20B—C29B	118.80 (13)	N1B—O1B—C4B	103.82 (10)
C21B—C20B—C2B	122.47 (13)	N1B—C2B—C20B	108.23 (11)
C29B—C20B—C2B	118.71 (12)	N1B—C2B—C3B	103.27 (11)
C20A—C21A—C22A	121.42 (13)	C20B—C2B—C3B	116.78 (12)
C23A—C22A—C21A	120.65 (13)	C4B—C3B—C2B	103.21 (11)
C22A—C23A—C24A	120.10 (13)	O1B—C4B—C5B	106.46 (11)
C25A—C24A—C23A	121.29 (13)	O1B—C4B—C3B	103.96 (11)
C25A—C24A—C29A	119.20 (13)	C5B—C4B—C3B	113.07 (12)
C23A—C24A—C29A	119.50 (13)	C4B—C5B—C5B2	109.53 (12)
C26A—C25A—C24A	120.98 (14)	C7B—C6B—C5B2	119.24 (14)
C25A—C26A—C27A	120.18 (13)	C7B—C6B—C6B2	120.32 (15)
C28A—C27A—C26A	120.43 (14)	C5B2—C6B—C6B2	120.43 (15)
C27A—C28A—C29A	121.00 (14)	C6B—C7B—C8B	122.15 (14)
C28A—C29A—C24A	118.20 (12)	C9B—C8B—C7B	118.17 (14)
C28A—C29A—C20A	122.77 (13)	C9B—C8B—C8B2	121.45 (15)
C24A—C29A—C20A	119.03 (13)	C7B—C8B—C8B2	120.34 (15)
C21A—C20A—C29A	119.28 (13)	C8B—C9B—C9B2	120.63 (14)
C21A—C20A—C2A	121.32 (12)	C9A2—C5A2—C6A	118.79 (13)
C29A—C20A—C2A	119.39 (12)	C9A2—C5A2—C5A	119.49 (13)
C9A2—N1A—O1A	108.10 (11)	C6A—C5A2—C5A	121.70 (13)
C9A2—N1A—C2A	111.22 (11)	C9A—C9A2—C5A2	121.22 (13)
O1A—N1A—C2A	102.50 (10)	C9A—C9A2—N1A	117.60 (13)
N1A—O1A—C4A	103.47 (10)	C5A2—C9A2—N1A	121.17 (13)
N1A—C2A—C20A	111.14 (11)	C6B—C5B2—C9B2	118.79 (14)
N1A—C2A—C3A	103.92 (11)	C6B—C5B2—C5B	121.89 (14)
C20A—C2A—C3A	113.39 (11)	C9B2—C5B2—C5B	119.31 (13)
C4A—C3A—C2A	102.99 (11)	C9B—C9B2—C5B2	120.99 (14)
O1A—C4A—C5A	107.67 (11)	C9B—C9B2—N1B	117.34 (13)
O1A—C4A—C3A	103.59 (11)	C5B2—C9B2—N1B	121.63 (13)

C20B—C21B—C22B—C23B	−0.2 (2)	C6A2—C6A—C7A—C8A	178.20 (13)
C21B—C22B—C23B—C24B	0.1 (2)	C6A—C7A—C8A—C9A	2.3 (2)
C29B—C28B—C27B—C26B	0.0 (2)	C6A—C7A—C8A—C8A2	−178.25 (13)
C28B—C27B—C26B—C25B	0.4 (2)	C7A—C8A—C9A—C9A2	−1.5 (2)
C27B—C26B—C25B—C24B	−0.1 (2)	C8A2—C8A—C9A—C9A2	179.07 (13)
C26B—C25B—C24B—C23B	179.56 (14)	C9B2—N1B—O1B—C4B	−66.29 (12)
C26B—C25B—C24B—C29B	−0.6 (2)	C2B—N1B—O1B—C4B	50.95 (12)
C22B—C23B—C24B—C25B	179.42 (14)	O1B—N1B—C2B—C20B	82.23 (12)
C22B—C23B—C24B—C29B	−0.4 (2)	C9B2—N1B—C2B—C20B	−163.33 (11)
C27B—C28B—C29B—C24B	−0.6 (2)	O1B—N1B—C2B—C3B	−42.17 (12)
C27B—C28B—C29B—C20B	179.27 (14)	C9B2—N1B—C2B—C3B	72.27 (13)
C25B—C24B—C29B—C28B	0.9 (2)	C21B—C20B—C2B—N1B	−103.42 (15)
C23B—C24B—C29B—C28B	−179.22 (13)	C29B—C20B—C2B—N1B	74.69 (15)
C25B—C24B—C29B—C20B	−179.01 (13)	C21B—C20B—C2B—C3B	12.5 (2)
C23B—C24B—C29B—C20B	0.9 (2)	C29B—C20B—C2B—C3B	−169.40 (12)
C22B—C21B—C20B—C29B	0.6 (2)	N1B—C2B—C3B—C4B	18.56 (14)
C22B—C21B—C20B—C2B	178.69 (13)	C20B—C2B—C3B—C4B	−100.06 (14)
C28B—C29B—C20B—C21B	179.16 (13)	N1B—O1B—C4B—C5B	80.74 (13)
C24B—C29B—C20B—C21B	−0.9 (2)	N1B—O1B—C4B—C3B	−38.89 (13)
C28B—C29B—C20B—C2B	1.0 (2)	C2B—C3B—C4B—O1B	11.42 (14)
C24B—C29B—C20B—C2B	−179.11 (12)	C2B—C3B—C4B—C5B	−103.62 (13)
C20A—C21A—C22A—C23A	−1.0 (2)	O1B—C4B—C5B—C5B2	−48.84 (15)
C21A—C22A—C23A—C24A	0.5 (2)	C3B—C4B—C5B—C5B2	64.69 (15)
C22A—C23A—C24A—C25A	−178.65 (14)	C5B2—C6B—C7B—C8B	0.0 (2)
C22A—C23A—C24A—C29A	0.6 (2)	C6B2—C6B—C7B—C8B	179.14 (14)
C23A—C24A—C25A—C26A	−179.84 (14)	C6B—C7B—C8B—C9B	0.8 (2)
C29A—C24A—C25A—C26A	0.9 (2)	C6B—C7B—C8B—C8B2	178.66 (14)
C24A—C25A—C26A—C27A	0.1 (2)	C7B—C8B—C9B—C9B2	−0.5 (2)
C25A—C26A—C27A—C28A	−0.8 (2)	C8B2—C8B—C9B—C9B2	−178.30 (13)
C26A—C27A—C28A—C29A	0.3 (2)	C7A—C6A—C5A2—C9A2	−2.9 (2)
C27A—C28A—C29A—C24A	0.7 (2)	C6A2—C6A—C5A2—C9A2	178.76 (13)
C27A—C28A—C29A—C20A	−178.61 (13)	C7A—C6A—C5A2—C5A	175.77 (13)
C25A—C24A—C29A—C28A	−1.35 (19)	C6A2—C6A—C5A2—C5A	−2.5 (2)
C23A—C24A—C29A—C28A	179.40 (13)	C4A—C5A—C5A2—C9A2	3.82 (17)
C25A—C24A—C29A—C20A	178.03 (12)	C4A—C5A—C5A2—C6A	−174.86 (12)
C23A—C24A—C29A—C20A	−1.22 (19)	C8A—C9A—C9A2—C5A2	−1.5 (2)
C22A—C21A—C20A—C29A	0.4 (2)	C8A—C9A—C9A2—N1A	178.84 (12)
C22A—C21A—C20A—C2A	179.38 (13)	C6A—C5A2—C9A2—C9A	3.8 (2)
C28A—C29A—C20A—C21A	−179.91 (13)	C5A—C5A2—C9A2—C9A	−174.96 (12)
C24A—C29A—C20A—C21A	0.7 (2)	C6A—C5A2—C9A2—N1A	−176.61 (12)
C28A—C29A—C20A—C2A	1.1 (2)	C5A—C5A2—C9A2—N1A	4.67 (19)
C24A—C29A—C20A—C2A	−178.28 (12)	O1A—N1A—C9A2—C9A	−152.72 (11)
C9A2—N1A—O1A—C4A	−68.06 (12)	C2A—N1A—C9A2—C9A	95.49 (14)
C2A—N1A—O1A—C4A	49.48 (12)	O1A—N1A—C9A2—C5A2	27.63 (16)
C9A2—N1A—C2A—C20A	−157.54 (12)	C2A—N1A—C9A2—C5A2	−84.15 (15)
O1A—N1A—C2A—C20A	87.16 (12)	C7B—C6B—C5B2—C9B2	−1.1 (2)
C9A2—N1A—C2A—C3A	80.15 (13)	C6B2—C6B—C5B2—C9B2	179.77 (13)
O1A—N1A—C2A—C3A	−35.15 (13)	C7B—C6B—C5B2—C5B	179.15 (13)
C21A—C20A—C2A—N1A	−10.41 (18)	C6B2—C6B—C5B2—C5B	0.0 (2)
C29A—C20A—C2A—N1A	168.59 (12)	C4B—C5B—C5B2—C6B	−171.67 (13)
C21A—C20A—C2A—C3A	106.23 (15)	C4B—C5B—C5B2—C9B2	8.55 (18)
C29A—C20A—C2A—C3A	−74.77 (16)	C8B—C9B—C9B2—C5B2	−0.6 (2)
N1A—C2A—C3A—C4A	9.28 (14)	C8B—C9B—C9B2—N1B	177.22 (12)
C20A—C2A—C3A—C4A	−111.52 (12)	C6B—C5B2—C9B2—C9B	1.4 (2)
N1A—O1A—C4A—C5A	78.62 (12)	C5B—C5B2—C9B2—C9B	−178.81 (13)
N1A—O1A—C4A—C3A	−42.92 (12)	C6B—C5B2—C9B2—N1B	−176.36 (12)
C2A—C3A—C4A—O1A	19.79 (14)	C5B—C5B2—C9B2—N1B	3.4 (2)
C2A—C3A—C4A—C5A	−97.11 (13)	O1B—N1B—C9B2—C9B	−152.18 (11)
O1A—C4A—C5A—C5A2	−44.43 (15)	C2B—N1B—C9B2—C9B	98.08 (14)
C3A—C4A—C5A—C5A2	70.10 (15)	O1B—N1B—C9B2—C5B2	25.66 (16)
C5A2—C6A—C7A—C8A	−0.1 (2)	C2B—N1B—C9B2—C5B2	−84.08 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A···O1Aⁱ	1.00	2.61	3.4061 (17)	137
C5A—H5AA···Cg_1A2ⁱⁱ	1.00	2.60	3.5600 (16)	163
C4B—H4B···O1Bⁱⁱⁱ	1.00	2.43	3.1601 (18)	129

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

(Compound_2) (2SR,4RS)-6,9-Dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine top

Crystal data top

C₂₂H₂₁NO	D_x = 1.217 Mg m⁻³
M_r = 315.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9810 reflections
a = 7.5541 (3) Å	θ = 2.8–23.6°
b = 14.7914 (5) Å	µ = 0.07 mm⁻¹
c = 15.4049 (5) Å	T = 298 K
V = 1721.28 (11) Å³	Parallelipiped, less
Z = 4	0.51 × 0.32 × 0.25 mm
F(000) = 672

Data collection top

Bruker Kappa APEXII diffractometer	4013 reflections with I > 2σ(I)
π and ω scans	R_int = 0.041
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 31.5°, θ_min = 2.6°
T_min = 0.86, T_max = 0.98	h = −11→11
69991 measured reflections	k = −21→21
5630 independent reflections	l = −21→20

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.043	w = 1/[σ²(F_o²) + (0.0474P)² + 0.1943P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.109	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.17 e Å⁻³
5630 reflections	Δρ_min = −0.16 e Å⁻³
220 parameters	Absolute structure: Refined as an inversion twin
0 restraints	Absolute structure parameter: 0 (2)

Crystal data top

C₂₂H₂₁NO	V = 1721.28 (11) Å³
M_r = 315.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.5541 (3) Å	µ = 0.07 mm⁻¹
b = 14.7914 (5) Å	T = 298 K
c = 15.4049 (5) Å	0.51 × 0.32 × 0.25 mm

Data collection top

Bruker Kappa APEXII diffractometer	5630 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	4013 reflections with I > 2σ(I)
T_min = 0.86, T_max = 0.98	R_int = 0.041
69991 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.17 e Å⁻³
S = 1.03	Δρ_min = −0.16 e Å⁻³
5630 reflections	Absolute structure: Refined as an inversion twin
220 parameters	Absolute structure parameter: 0 (2)
0 restraints

Special details top

Refinement. Refined as a 2-component inversion twin

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

	x	y	z	U_iso*/U_eq
N1	0.9800 (2)	0.52882 (10)	0.31021 (10)	0.0423 (3)
O1	0.9286 (2)	0.43694 (9)	0.33014 (10)	0.0568 (4)
C2	0.9364 (2)	0.57663 (11)	0.39184 (11)	0.0377 (4)
H2	0.9125	0.6403	0.3788	0.045*
C3	0.7626 (3)	0.53080 (15)	0.42245 (13)	0.0485 (4)
H3A	0.7685	0.5151	0.4835	0.058*
H3B	0.6614	0.5699	0.4129	0.058*
C4	0.7519 (3)	0.44603 (14)	0.36570 (14)	0.0577 (5)
H4	0.7213	0.3931	0.4009	0.069*
C5	0.6282 (3)	0.45441 (15)	0.28903 (15)	0.0612 (6)
H5A	0.6195	0.3968	0.2592	0.073*
H5B	0.5109	0.4713	0.3089	0.073*
C6	0.5982 (3)	0.55849 (14)	0.15960 (12)	0.0501 (5)
H6	0.4869	0.5341	0.1488	0.060*
C7	0.6613 (3)	0.62674 (14)	0.10782 (13)	0.0509 (5)
H7	0.5918	0.6478	0.0623	0.061*
C8	0.8273 (3)	0.66520 (12)	0.12205 (12)	0.0461 (4)
C9	0.9331 (2)	0.63197 (12)	0.18904 (11)	0.0407 (4)
C20	1.0829 (2)	0.57094 (11)	0.45868 (11)	0.0392 (4)
C21	1.2146 (3)	0.50741 (14)	0.45314 (14)	0.0492 (5)
H21	1.2173	0.4679	0.4062	0.059*
C22	1.3460 (3)	0.50135 (16)	0.51779 (16)	0.0607 (6)
H22	1.4333	0.4572	0.5134	0.073*
C23	1.3470 (3)	0.55880 (16)	0.58620 (15)	0.0601 (6)
H23	1.4357	0.5541	0.6278	0.072*
C24	1.2156 (3)	0.62541 (14)	0.59503 (13)	0.0488 (5)
C25	1.2122 (4)	0.68617 (16)	0.66644 (14)	0.0626 (6)
H25	1.2999	0.6821	0.7086	0.075*
C26	1.0850 (4)	0.74953 (16)	0.67460 (14)	0.0661 (7)
H26	1.0858	0.7886	0.7219	0.079*
C27	0.9521 (4)	0.75635 (14)	0.61188 (14)	0.0611 (6)
H27	0.8648	0.8003	0.6177	0.073*
C28	0.9485 (3)	0.69931 (13)	0.54195 (13)	0.0499 (5)
H28	0.8584	0.7046	0.5012	0.060*
C82	0.8909 (4)	0.74143 (16)	0.06431 (15)	0.0690 (7)
H82A	0.9963	0.7230	0.0344	0.104*
H82B	0.9161	0.7936	0.0992	0.104*
H82C	0.8005	0.7560	0.0228	0.104*
C92	1.1147 (3)	0.67050 (16)	0.20596 (15)	0.0568 (5)
H92A	1.1760	0.6781	0.1519	0.085*
H92B	1.1801	0.6299	0.2425	0.085*
H92C	1.1034	0.7280	0.2343	0.085*
C29	1.0806 (2)	0.63220 (12)	0.53094 (11)	0.0410 (4)
C5A	0.6987 (3)	0.52552 (12)	0.22777 (12)	0.0443 (4)
C9A	0.8675 (2)	0.56170 (11)	0.24071 (11)	0.0384 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0461 (8)	0.0365 (7)	0.0444 (8)	0.0033 (6)	0.0020 (7)	−0.0003 (6)
O1	0.0657 (9)	0.0355 (6)	0.0692 (9)	0.0050 (7)	−0.0012 (8)	0.0036 (6)
C2	0.0380 (8)	0.0373 (8)	0.0380 (8)	0.0039 (7)	0.0012 (7)	0.0031 (7)
C3	0.0395 (9)	0.0625 (11)	0.0435 (10)	−0.0025 (8)	−0.0005 (8)	0.0102 (9)
C4	0.0630 (13)	0.0467 (11)	0.0633 (13)	−0.0132 (10)	−0.0025 (10)	0.0147 (10)
C5	0.0634 (13)	0.0558 (12)	0.0645 (13)	−0.0229 (10)	−0.0061 (11)	0.0019 (10)
C6	0.0475 (11)	0.0545 (10)	0.0484 (10)	−0.0077 (9)	−0.0069 (9)	−0.0148 (9)
C7	0.0582 (12)	0.0535 (10)	0.0410 (10)	0.0029 (10)	−0.0102 (9)	−0.0068 (9)
C8	0.0582 (12)	0.0444 (9)	0.0356 (9)	0.0014 (8)	0.0018 (8)	−0.0049 (8)
C9	0.0433 (9)	0.0424 (8)	0.0363 (8)	−0.0003 (8)	0.0039 (7)	−0.0072 (7)
C20	0.0353 (8)	0.0385 (8)	0.0439 (9)	−0.0005 (7)	0.0010 (7)	0.0107 (7)
C21	0.0407 (10)	0.0476 (10)	0.0593 (11)	0.0042 (8)	0.0019 (9)	0.0096 (9)
C22	0.0370 (10)	0.0629 (13)	0.0823 (16)	0.0086 (9)	−0.0019 (10)	0.0257 (12)
C23	0.0427 (11)	0.0694 (13)	0.0682 (13)	−0.0091 (10)	−0.0185 (10)	0.0267 (12)
C24	0.0458 (10)	0.0515 (10)	0.0492 (10)	−0.0164 (9)	−0.0089 (9)	0.0194 (9)
C25	0.0709 (15)	0.0672 (14)	0.0496 (11)	−0.0296 (13)	−0.0192 (11)	0.0122 (10)
C26	0.0900 (18)	0.0605 (13)	0.0477 (11)	−0.0238 (14)	−0.0030 (12)	−0.0040 (10)
C27	0.0774 (16)	0.0526 (11)	0.0533 (11)	−0.0014 (11)	0.0038 (11)	−0.0043 (10)
C28	0.0568 (12)	0.0472 (10)	0.0458 (10)	0.0028 (9)	−0.0060 (9)	0.0012 (8)
C82	0.0864 (18)	0.0655 (13)	0.0552 (12)	−0.0094 (13)	−0.0058 (12)	0.0149 (11)
C92	0.0458 (11)	0.0675 (13)	0.0572 (12)	−0.0125 (10)	0.0024 (10)	0.0045 (10)
C29	0.0425 (9)	0.0407 (8)	0.0397 (9)	−0.0071 (8)	−0.0034 (8)	0.0108 (7)
C5A	0.0483 (10)	0.0402 (8)	0.0443 (9)	−0.0050 (8)	−0.0008 (8)	−0.0082 (7)
C9A	0.0422 (9)	0.0359 (7)	0.0371 (8)	0.0034 (7)	0.0023 (7)	−0.0085 (7)

Geometric parameters (Å, º) top

N1—O1	1.446 (2)	C9—C9A	1.400 (2)
N1—C9A	1.451 (2)	C9—C92	1.508 (3)
N1—C2	1.480 (2)	C20—C21	1.371 (3)
O1—C4	1.450 (3)	C20—C29	1.435 (3)
C2—C20	1.514 (2)	C21—C22	1.409 (3)
C2—C3	1.551 (3)	C22—C23	1.354 (3)
C3—C4	1.531 (3)	C23—C24	1.405 (3)
C4—C5	1.511 (3)	C24—C25	1.421 (3)
C5—C5A	1.510 (3)	C24—C29	1.423 (3)
C6—C7	1.372 (3)	C25—C26	1.348 (4)
C6—C5A	1.384 (3)	C26—C27	1.397 (4)
C7—C8	1.395 (3)	C27—C28	1.369 (3)
C8—C9	1.395 (3)	C28—C29	1.418 (3)
C8—C82	1.514 (3)	C5A—C9A	1.397 (3)

O1—N1—C9A	108.33 (14)	C21—C20—C2	121.75 (17)
O1—N1—C2	102.06 (13)	C29—C20—C2	118.92 (15)
C9A—N1—C2	109.66 (13)	C20—C21—C22	120.7 (2)
N1—O1—C4	103.89 (14)	C23—C22—C21	121.0 (2)
N1—C2—C20	112.86 (14)	C22—C23—C24	120.77 (19)
N1—C2—C3	103.77 (14)	C23—C24—C25	122.1 (2)
C20—C2—C3	112.82 (14)	C23—C24—C29	119.2 (2)
C4—C3—C2	103.24 (16)	C25—C24—C29	118.6 (2)
O1—C4—C5	106.37 (18)	C26—C25—C24	121.7 (2)
O1—C4—C3	104.08 (16)	C25—C26—C27	119.9 (2)
C5—C4—C3	114.32 (18)	C28—C27—C26	120.9 (2)
C5A—C5—C4	109.11 (17)	C27—C28—C29	120.8 (2)
C7—C6—C5A	120.65 (19)	C28—C29—C24	118.09 (18)
C6—C7—C8	121.40 (19)	C28—C29—C20	122.90 (16)
C9—C8—C7	119.21 (18)	C24—C29—C20	119.01 (18)
C9—C8—C82	121.02 (19)	C6—C5A—C9A	118.28 (18)
C7—C8—C82	119.77 (19)	C6—C5A—C5	121.72 (18)
C8—C9—C9A	118.63 (17)	C9A—C5A—C5	119.97 (18)
C8—C9—C92	121.06 (17)	C5A—C9A—C9	121.78 (17)
C9A—C9—C92	120.31 (17)	C5A—C9A—N1	120.77 (16)
C21—C20—C29	119.30 (17)	C9—C9A—N1	117.44 (16)

C9A—N1—O1—C4	−66.50 (17)	C23—C24—C25—C26	−179.6 (2)
C2—N1—O1—C4	49.16 (17)	C29—C24—C25—C26	−0.1 (3)
O1—N1—C2—C20	84.80 (17)	C24—C25—C26—C27	0.2 (3)
C9A—N1—C2—C20	−160.50 (14)	C25—C26—C27—C28	0.1 (3)
O1—N1—C2—C3	−37.66 (16)	C26—C27—C28—C29	−0.5 (3)
C9A—N1—C2—C3	77.04 (16)	C27—C28—C29—C24	0.6 (3)
N1—C2—C3—C4	13.45 (17)	C27—C28—C29—C20	−179.87 (18)
C20—C2—C3—C4	−109.03 (17)	C23—C24—C29—C28	179.27 (18)
N1—O1—C4—C5	81.05 (18)	C25—C24—C29—C28	−0.3 (2)
N1—O1—C4—C3	−40.02 (18)	C23—C24—C29—C20	−0.3 (2)
C2—C3—C4—O1	15.50 (18)	C25—C24—C29—C20	−179.85 (17)
C2—C3—C4—C5	−100.11 (19)	C21—C20—C29—C28	−179.47 (18)
O1—C4—C5—C5A	−49.5 (2)	C2—C20—C29—C28	−1.2 (3)
C3—C4—C5—C5A	64.8 (2)	C21—C20—C29—C24	0.1 (2)
C5A—C6—C7—C8	−0.2 (3)	C2—C20—C29—C24	178.37 (15)
C6—C7—C8—C9	1.6 (3)	C7—C6—C5A—C9A	−1.9 (3)
C6—C7—C8—C82	−179.03 (19)	C7—C6—C5A—C5	176.3 (2)
C7—C8—C9—C9A	−0.9 (3)	C4—C5—C5A—C6	−168.88 (18)
C82—C8—C9—C9A	179.70 (18)	C4—C5—C5A—C9A	9.2 (3)
C7—C8—C9—C92	179.07 (18)	C6—C5A—C9A—C9	2.5 (3)
C82—C8—C9—C92	−0.3 (3)	C5—C5A—C9A—C9	−175.63 (17)
N1—C2—C20—C21	−17.7 (2)	C6—C5A—C9A—N1	−178.99 (16)
C3—C2—C20—C21	99.5 (2)	C5—C5A—C9A—N1	2.9 (3)
N1—C2—C20—C29	164.02 (15)	C8—C9—C9A—C5A	−1.1 (2)
C3—C2—C20—C29	−78.74 (19)	C92—C9—C9A—C5A	178.87 (17)
C29—C20—C21—C22	0.6 (3)	C8—C9—C9A—N1	−179.66 (15)
C2—C20—C21—C22	−177.71 (17)	C92—C9—C9A—N1	0.3 (2)
C20—C21—C22—C23	−1.0 (3)	O1—N1—C9A—C5A	25.6 (2)
C21—C22—C23—C24	0.7 (3)	C2—N1—C9A—C5A	−84.97 (19)
C22—C23—C24—C25	179.44 (19)	O1—N1—C9A—C9	−155.80 (14)
C22—C23—C24—C29	−0.1 (3)	C2—N1—C9A—C9	93.59 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C82—H82···O1ⁱ	0.96	2.66	3.587 (3)	164

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

(Compound_3) (2SR,4RS)-8,9-Dimethyl-2-(naphthalen-1-yl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine top

Crystal data top

C₂₂H₂₁NO	F(000) = 336
M_r = 315.40	D_x = 1.262 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 7.2201 (2) Å	Cell parameters from 9843 reflections
b = 7.8128 (3) Å	θ = 2.8–30.2°
c = 14.7409 (5) Å	µ = 0.08 mm⁻¹
β = 93.690 (2)°	T = 100 K
V = 829.80 (5) Å³	Paralelipiped, less
Z = 2	0.30 × 0.30 × 0.15 mm

Data collection top

Bruker Kappa APEXII diffractometer	4638 reflections with I > 2σ(I)
π and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 30.3°, θ_min = 1.4°
T_min = 0.92, T_max = 0.99	h = −10→10
27947 measured reflections	k = −11→11
4874 independent reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0566P)² + 0.1148P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4874 reflections	Δρ_max = 0.30 e Å⁻³
219 parameters	Δρ_min = −0.19 e Å⁻³
1 restraint	Absolute structure: Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: iterative	Absolute structure parameter: −0.1 (3)

Crystal data top

C₂₂H₂₁NO	V = 829.80 (5) Å³
M_r = 315.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.2201 (2) Å	µ = 0.08 mm⁻¹
b = 7.8128 (3) Å	T = 100 K
c = 14.7409 (5) Å	0.30 × 0.30 × 0.15 mm
β = 93.690 (2)°

Data collection top

Bruker Kappa APEXII diffractometer	4874 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	4638 reflections with I > 2σ(I)
T_min = 0.92, T_max = 0.99	R_int = 0.023
27947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.092	Δρ_max = 0.30 e Å⁻³
S = 1.04	Δρ_min = −0.19 e Å⁻³
4874 reflections	Absolute structure: Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
219 parameters	Absolute structure parameter: −0.1 (3)
1 restraint

Special details top

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

	x	y	z	U_iso*/U_eq
N1	0.15129 (17)	0.35804 (16)	0.21245 (8)	0.0165 (2)
O1	0.09164 (15)	0.19439 (14)	0.17551 (7)	0.0205 (2)
C2	0.08542 (18)	0.35174 (18)	0.30555 (9)	0.0150 (2)
H2	0.0643	0.4709	0.3274	0.018*
C3	−0.10421 (19)	0.2564 (2)	0.29297 (10)	0.0187 (3)
H3A	−0.1127	0.1637	0.3383	0.022*
H3B	−0.2094	0.3364	0.2983	0.022*
C4	−0.1017 (2)	0.1839 (2)	0.19629 (10)	0.0209 (3)
H4	−0.1451	0.0624	0.1945	0.025*
C5	−0.2114 (2)	0.2901 (2)	0.12504 (10)	0.0227 (3)
H5A	−0.2169	0.2296	0.0659	0.027*
H5B	−0.3399	0.3060	0.1432	0.027*
C6	−0.2051 (2)	0.5930 (2)	0.06265 (10)	0.0230 (3)
C7	−0.1176 (2)	0.7511 (2)	0.05942 (10)	0.0254 (3)
H7	−0.1746	0.8403	0.0238	0.030*
C8	0.0513 (2)	0.7813 (2)	0.10715 (10)	0.0230 (3)
H8	0.1064	0.8915	0.1050	0.028*
C9	0.1414 (2)	0.65198 (18)	0.15833 (9)	0.0189 (3)
C20	0.22202 (18)	0.26185 (18)	0.37162 (9)	0.0149 (2)
C21	0.37597 (19)	0.1793 (2)	0.34334 (10)	0.0189 (3)
H21	0.4001	0.1809	0.2807	0.023*
C22	0.4994 (2)	0.0918 (2)	0.40580 (11)	0.0227 (3)
H22	0.6040	0.0340	0.3846	0.027*
C23	0.46936 (19)	0.0897 (2)	0.49629 (11)	0.0218 (3)
H23	0.5533	0.0309	0.5376	0.026*
C24	0.31329 (18)	0.17489 (19)	0.52887 (9)	0.0170 (3)
C25	0.2805 (2)	0.1761 (2)	0.62270 (10)	0.0208 (3)
H25	0.3651	0.1193	0.6646	0.025*
C26	0.1294 (2)	0.2575 (2)	0.65411 (10)	0.0220 (3)
H26	0.1100	0.2576	0.7172	0.026*
C27	0.0027 (2)	0.3414 (2)	0.59219 (10)	0.0210 (3)
H27	−0.1031	0.3966	0.6138	0.025*
C28	0.03096 (19)	0.34389 (19)	0.50090 (10)	0.0178 (3)
H28	−0.0552	0.4018	0.4603	0.021*
C62	−0.3885 (2)	0.5624 (3)	0.01018 (12)	0.0316 (4)
H62A	−0.4141	0.6570	−0.0325	0.047*
H62B	−0.4874	0.5558	0.0525	0.047*
H62C	−0.3829	0.4547	−0.0236	0.047*
C92	0.3224 (2)	0.6848 (2)	0.21182 (10)	0.0230 (3)
H92A	0.4071	0.5888	0.2037	0.035*
H92B	0.3000	0.6965	0.2764	0.035*
H92C	0.3779	0.7905	0.1902	0.035*
C29	0.18719 (18)	0.26126 (18)	0.46621 (9)	0.0147 (2)
C5A	−0.1198 (2)	0.46197 (19)	0.11569 (9)	0.0193 (3)
C9A	0.0542 (2)	0.49217 (18)	0.16048 (9)	0.0170 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0208 (5)	0.0128 (5)	0.0158 (5)	0.0005 (4)	0.0010 (4)	−0.0013 (4)
O1	0.0228 (5)	0.0150 (5)	0.0240 (5)	−0.0001 (4)	0.0026 (4)	−0.0053 (4)
C2	0.0153 (5)	0.0133 (6)	0.0165 (5)	0.0015 (5)	0.0019 (4)	0.0008 (5)
C3	0.0171 (6)	0.0178 (6)	0.0210 (6)	−0.0004 (5)	0.0003 (5)	0.0013 (5)
C4	0.0217 (6)	0.0162 (6)	0.0247 (6)	−0.0019 (5)	0.0009 (5)	−0.0031 (6)
C5	0.0229 (7)	0.0239 (7)	0.0208 (6)	−0.0028 (6)	−0.0030 (5)	−0.0036 (5)
C6	0.0242 (7)	0.0286 (8)	0.0160 (6)	0.0067 (6)	0.0002 (5)	−0.0013 (6)
C7	0.0318 (8)	0.0257 (7)	0.0188 (6)	0.0095 (6)	0.0031 (6)	0.0045 (6)
C8	0.0311 (7)	0.0187 (7)	0.0197 (6)	0.0026 (6)	0.0066 (6)	0.0029 (5)
C9	0.0230 (7)	0.0187 (7)	0.0154 (6)	−0.0001 (5)	0.0033 (5)	0.0003 (5)
C20	0.0151 (5)	0.0113 (5)	0.0182 (6)	0.0002 (5)	0.0012 (4)	0.0010 (5)
C21	0.0176 (6)	0.0160 (6)	0.0234 (6)	0.0014 (5)	0.0048 (5)	0.0015 (6)
C22	0.0160 (6)	0.0200 (7)	0.0328 (8)	0.0057 (6)	0.0061 (5)	0.0055 (6)
C23	0.0161 (6)	0.0191 (7)	0.0299 (7)	0.0026 (5)	−0.0009 (5)	0.0067 (6)
C24	0.0154 (6)	0.0134 (6)	0.0218 (6)	−0.0016 (5)	−0.0007 (5)	0.0030 (5)
C25	0.0233 (7)	0.0178 (6)	0.0208 (6)	−0.0055 (5)	−0.0030 (5)	0.0049 (6)
C26	0.0301 (7)	0.0179 (6)	0.0181 (6)	−0.0078 (6)	0.0031 (5)	0.0004 (5)
C27	0.0250 (7)	0.0161 (6)	0.0227 (7)	−0.0012 (6)	0.0075 (5)	−0.0008 (6)
C28	0.0188 (6)	0.0141 (6)	0.0206 (6)	0.0022 (5)	0.0025 (5)	0.0003 (5)
C62	0.0271 (8)	0.0422 (10)	0.0246 (7)	0.0097 (7)	−0.0056 (6)	−0.0028 (7)
C92	0.0255 (7)	0.0223 (7)	0.0212 (6)	−0.0057 (6)	0.0013 (5)	0.0005 (6)
C29	0.0150 (5)	0.0108 (5)	0.0183 (6)	−0.0009 (5)	0.0013 (4)	0.0009 (5)
C5A	0.0216 (6)	0.0201 (7)	0.0161 (6)	0.0014 (5)	0.0000 (5)	−0.0023 (5)
C9A	0.0209 (6)	0.0167 (6)	0.0136 (5)	0.0022 (5)	0.0014 (5)	−0.0004 (5)

Geometric parameters (Å, º) top

N1—O1	1.4445 (15)	C9—C9A	1.400 (2)
N1—C9A	1.4516 (18)	C9—C92	1.504 (2)
N1—C2	1.4819 (17)	C20—C21	1.3730 (19)
O1—C4	1.4504 (18)	C20—C29	1.4328 (17)
C2—C20	1.5135 (18)	C21—C22	1.415 (2)
C2—C3	1.5591 (19)	C22—C23	1.365 (2)
C3—C4	1.535 (2)	C23—C24	1.419 (2)
C4—C5	1.520 (2)	C24—C25	1.4182 (19)
C5—C5A	1.507 (2)	C24—C29	1.4245 (17)
C6—C7	1.390 (2)	C25—C26	1.369 (2)
C6—C5A	1.406 (2)	C26—C27	1.411 (2)
C6—C62	1.509 (2)	C27—C28	1.374 (2)
C7—C8	1.389 (2)	C28—C29	1.4229 (18)
C8—C9	1.396 (2)	C5A—C9A	1.4008 (19)

O1—N1—C9A	108.54 (10)	C21—C20—C2	121.96 (12)
O1—N1—C2	102.36 (10)	C29—C20—C2	118.67 (11)
C9A—N1—C2	109.87 (11)	C20—C21—C22	121.16 (13)
N1—O1—C4	103.76 (10)	C23—C22—C21	120.57 (13)
N1—C2—C20	112.13 (11)	C22—C23—C24	120.30 (13)
N1—C2—C3	103.74 (11)	C25—C24—C23	121.29 (13)
C20—C2—C3	112.69 (11)	C25—C24—C29	119.29 (12)
C4—C3—C2	102.93 (11)	C23—C24—C29	119.42 (12)
O1—C4—C5	106.80 (12)	C26—C25—C24	121.31 (13)
O1—C4—C3	104.16 (11)	C25—C26—C27	119.64 (13)
C5—C4—C3	113.79 (13)	C28—C27—C26	120.60 (14)
C5A—C5—C4	109.70 (12)	C27—C28—C29	121.10 (13)
C7—C6—C5A	118.84 (14)	C28—C29—C24	118.05 (12)
C7—C6—C62	120.59 (15)	C28—C29—C20	122.76 (12)
C5A—C6—C62	120.57 (16)	C24—C29—C20	119.19 (11)
C8—C7—C6	121.34 (15)	C9A—C5A—C6	119.15 (14)
C7—C8—C9	120.94 (15)	C9A—C5A—C5	119.50 (13)
C8—C9—C9A	117.59 (14)	C6—C5A—C5	121.36 (14)
C8—C9—C92	121.23 (14)	C9—C9A—C5A	122.05 (13)
C9A—C9—C92	121.14 (13)	C9—C9A—N1	116.95 (12)
C21—C20—C29	119.36 (12)	C5A—C9A—N1	121.00 (13)

C9A—N1—O1—C4	−66.84 (13)	C24—C25—C26—C27	0.3 (2)
C2—N1—O1—C4	49.28 (12)	C25—C26—C27—C28	−0.9 (2)
O1—N1—C2—C20	84.76 (12)	C26—C27—C28—C29	0.5 (2)
C9A—N1—C2—C20	−160.08 (11)	C27—C28—C29—C24	0.3 (2)
O1—N1—C2—C3	−37.12 (12)	C27—C28—C29—C20	−179.63 (13)
C9A—N1—C2—C3	78.04 (13)	C25—C24—C29—C28	−0.81 (19)
N1—C2—C3—C4	12.43 (14)	C23—C24—C29—C28	179.32 (14)
C20—C2—C3—C4	−109.07 (13)	C25—C24—C29—C20	179.14 (14)
N1—O1—C4—C5	79.98 (13)	C23—C24—C29—C20	−0.73 (19)
N1—O1—C4—C3	−40.73 (13)	C21—C20—C29—C28	179.95 (14)
C2—C3—C4—O1	16.50 (15)	C2—C20—C29—C28	−1.0 (2)
C2—C3—C4—C5	−99.41 (14)	C21—C20—C29—C24	0.01 (19)
O1—C4—C5—C5A	−48.20 (15)	C2—C20—C29—C24	179.07 (12)
C3—C4—C5—C5A	66.15 (16)	C7—C6—C5A—C9A	−2.7 (2)
C5A—C6—C7—C8	0.1 (2)	C62—C6—C5A—C9A	177.31 (13)
C62—C6—C7—C8	−179.88 (14)	C7—C6—C5A—C5	177.46 (14)
C6—C7—C8—C9	1.6 (2)	C62—C6—C5A—C5	−2.5 (2)
C7—C8—C9—C9A	−0.7 (2)	C4—C5—C5A—C9A	8.16 (18)
C7—C8—C9—C92	−178.66 (14)	C4—C5—C5A—C6	−172.01 (13)
N1—C2—C20—C21	−7.43 (19)	C8—C9—C9A—C5A	−1.9 (2)
C3—C2—C20—C21	109.19 (15)	C92—C9—C9A—C5A	176.00 (13)
N1—C2—C20—C29	173.53 (12)	C8—C9—C9A—N1	178.78 (12)
C3—C2—C20—C29	−69.86 (16)	C92—C9—C9A—N1	−3.28 (19)
C29—C20—C21—C22	0.8 (2)	C6—C5A—C9A—C9	3.7 (2)
C2—C20—C21—C22	−178.19 (14)	C5—C5A—C9A—C9	−176.48 (13)
C20—C21—C22—C23	−1.0 (2)	C6—C5A—C9A—N1	−177.07 (12)
C21—C22—C23—C24	0.2 (2)	C5—C5A—C9A—N1	2.8 (2)
C22—C23—C24—C25	−179.25 (14)	O1—N1—C9A—C9	−154.16 (12)
C22—C23—C24—C29	0.6 (2)	C2—N1—C9A—C9	94.67 (14)
C23—C24—C25—C26	−179.64 (14)	O1—N1—C9A—C5A	26.55 (16)
C29—C24—C25—C26	0.5 (2)	C2—N1—C9A—C5A	−84.62 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.95	2.59	3.3880 (19)	142
C27—H27···Cg₃₁ⁱⁱ	0.95	2.86	3.6294 (16)	139
C28—H28···Cg₃₂ⁱⁱ	0.95	2.90	3.6116 (16)	133

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

(Compound_4) 7-Fluoro-cis-2-[(E)-styryl]-2,3,4,5-tetrahydro-1H-1-\ benzazepin-4-ol top

Crystal data top

C₁₈H₁₈FNO	D_x = 1.281 Mg m⁻³
M_r = 283.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9770 reflections
a = 7.5932 (3) Å	θ = 2.4–29.8°
b = 7.5859 (4) Å	µ = 0.09 mm⁻¹
c = 51.010 (3) Å	T = 100 K
V = 2938.2 (2) Å³	Parallelepiped, less
Z = 8	0.30 × 0.25 × 0.20 mm
F(000) = 1200

Data collection top

Bruker Kappa APEXII diffractometer	3407 reflections with I > 2σ(I)
π and ω scans	R_int = 0.027
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 30.3°, θ_min = 1.6°
T_min = 0.90, T_max = 0.98	h = −10→10
40696 measured reflections	k = −10→10
3764 independent reflections	l = −67→69

Refinement top

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)] = 0.045	Hydrogen site location: mixed
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0371P)² + 2.0455P] where P = (F_o² + 2F_c²)/3
3764 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₈FNO	V = 2938.2 (2) Å³
M_r = 283.33	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.5932 (3) Å	µ = 0.09 mm⁻¹
b = 7.5859 (4) Å	T = 100 K
c = 51.010 (3) Å	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	3764 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3407 reflections with I > 2σ(I)
T_min = 0.90, T_max = 0.98	R_int = 0.027
40696 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.108	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.32 e Å⁻³
3764 reflections	Δρ_min = −0.23 e Å⁻³
198 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.58993 (12)	0.76036 (12)	0.39113 (2)	0.0191 (2)
N1	0.52091 (13)	0.18488 (14)	0.39564 (2)	0.0147 (2)
F1	0.41254 (14)	0.24707 (13)	0.50268 (2)	0.0359 (2)
C2	0.42190 (15)	0.29702 (16)	0.37707 (2)	0.0149 (2)
H2	0.3001	0.3145	0.3841	0.018*
C3	0.50905 (16)	0.47789 (16)	0.37386 (2)	0.0159 (2)
H3A	0.6324	0.4595	0.3682	0.019*
H3B	0.4478	0.5417	0.3596	0.019*
C4	0.51013 (16)	0.59518 (16)	0.39810 (2)	0.0163 (2)
H4	0.3853	0.6182	0.4033	0.020*
C5	0.60719 (16)	0.51906 (16)	0.42174 (2)	0.0161 (2)
H5A	0.7259	0.4823	0.4159	0.019*
H5B	0.6234	0.6151	0.4347	0.019*
C6	0.49800 (17)	0.37683 (17)	0.46270 (2)	0.0204 (3)
H6	0.5217	0.4839	0.4717	0.025*
C7	0.43774 (18)	0.23177 (19)	0.47628 (2)	0.0230 (3)
C8	0.40179 (17)	0.07342 (18)	0.46443 (3)	0.0213 (3)
H8	0.3626	−0.0252	0.4743	0.026*
C9	0.42478 (16)	0.06272 (17)	0.43749 (2)	0.0178 (2)
H9	0.3990	−0.0447	0.4287	0.021*
C21	0.40917 (16)	0.21035 (17)	0.35058 (2)	0.0175 (2)
H21	0.3378	0.2677	0.3379	0.021*
C22	0.48755 (16)	0.06184 (17)	0.34316 (2)	0.0189 (3)
H22	0.5561	0.0026	0.3560	0.023*
C23	0.47892 (17)	−0.02029 (17)	0.31701 (2)	0.0194 (3)
C24	0.59407 (19)	−0.1587 (2)	0.31126 (3)	0.0260 (3)
H24	0.6742	−0.1984	0.3243	0.031*
C25	0.5932 (2)	−0.2391 (2)	0.28677 (3)	0.0305 (3)
H25	0.6731	−0.3322	0.2831	0.037*
C26	0.4756 (2)	−0.1834 (2)	0.26774 (3)	0.0287 (3)
H26	0.4751	−0.2376	0.2510	0.034*
C27	0.3588 (2)	−0.04858 (19)	0.27327 (3)	0.0268 (3)
H27	0.2773	−0.0113	0.2603	0.032*
C28	0.35978 (19)	0.03281 (18)	0.29769 (2)	0.0230 (3)
H28	0.2788	0.1252	0.3013	0.028*
C5A	0.52398 (15)	0.36544 (16)	0.43571 (2)	0.0156 (2)
C9A	0.48504 (15)	0.20665 (16)	0.42300 (2)	0.0145 (2)
H1N	0.503 (2)	0.071 (2)	0.3910 (3)	0.016 (4)*
H1O	0.705 (3)	0.743 (3)	0.3911 (3)	0.038 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0207 (4)	0.0099 (4)	0.0268 (5)	−0.0010 (3)	−0.0003 (4)	0.0033 (3)
N1	0.0191 (5)	0.0097 (5)	0.0153 (5)	0.0002 (4)	−0.0008 (4)	0.0010 (4)
F1	0.0618 (6)	0.0304 (5)	0.0156 (4)	−0.0003 (4)	0.0054 (4)	0.0026 (3)
C2	0.0149 (5)	0.0127 (6)	0.0170 (5)	−0.0006 (4)	−0.0016 (4)	0.0019 (4)
C3	0.0172 (5)	0.0124 (5)	0.0181 (5)	−0.0004 (4)	−0.0010 (4)	0.0034 (4)
C4	0.0164 (5)	0.0101 (5)	0.0222 (6)	−0.0006 (4)	0.0005 (4)	0.0029 (4)
C5	0.0182 (5)	0.0115 (5)	0.0185 (5)	−0.0013 (4)	−0.0012 (4)	−0.0002 (4)
C6	0.0270 (6)	0.0166 (6)	0.0177 (6)	0.0022 (5)	−0.0009 (5)	−0.0007 (5)
C7	0.0297 (6)	0.0251 (7)	0.0142 (5)	0.0032 (6)	0.0006 (5)	0.0039 (5)
C8	0.0232 (6)	0.0192 (6)	0.0214 (6)	−0.0011 (5)	0.0003 (5)	0.0077 (5)
C9	0.0177 (5)	0.0145 (6)	0.0213 (6)	−0.0017 (5)	−0.0027 (4)	0.0028 (5)
C21	0.0191 (5)	0.0162 (6)	0.0171 (5)	−0.0031 (5)	−0.0039 (4)	0.0030 (4)
C22	0.0198 (6)	0.0200 (6)	0.0168 (6)	−0.0003 (5)	−0.0034 (4)	0.0011 (5)
C23	0.0235 (6)	0.0170 (6)	0.0178 (6)	−0.0033 (5)	0.0000 (5)	0.0007 (5)
C24	0.0275 (7)	0.0266 (7)	0.0240 (6)	0.0029 (6)	−0.0017 (5)	−0.0016 (5)
C25	0.0342 (7)	0.0289 (8)	0.0283 (7)	0.0014 (6)	0.0042 (6)	−0.0065 (6)
C26	0.0407 (8)	0.0270 (7)	0.0184 (6)	−0.0099 (6)	0.0042 (6)	−0.0034 (5)
C27	0.0401 (8)	0.0233 (7)	0.0170 (6)	−0.0078 (6)	−0.0048 (5)	0.0033 (5)
C28	0.0311 (7)	0.0180 (6)	0.0200 (6)	−0.0015 (5)	−0.0036 (5)	0.0018 (5)
C5A	0.0156 (5)	0.0134 (6)	0.0176 (5)	0.0025 (4)	−0.0008 (4)	0.0014 (4)
C9A	0.0131 (5)	0.0146 (6)	0.0158 (5)	0.0012 (4)	−0.0014 (4)	0.0016 (4)

Geometric parameters (Å, º) top

O1—C4	1.4367 (14)	C8—C9	1.3880 (17)
N1—C9A	1.4312 (15)	C9—C9A	1.3957 (17)
N1—C2	1.4786 (15)	C21—C22	1.3292 (18)
F1—C7	1.3649 (14)	C22—C23	1.4739 (17)
C2—C21	1.5058 (17)	C23—C28	1.3970 (18)
C2—C3	1.5321 (16)	C23—C24	1.3974 (19)
C3—C4	1.5235 (17)	C24—C25	1.390 (2)
C4—C5	1.5264 (16)	C25—C26	1.385 (2)
C5—C5A	1.5050 (16)	C26—C27	1.382 (2)
C6—C7	1.3785 (19)	C27—C28	1.3904 (18)
C6—C5A	1.3936 (17)	C5A—C9A	1.3995 (17)
C7—C8	1.372 (2)

C9A—N1—C2	117.48 (10)	C21—C22—C23	126.59 (12)
N1—C2—C21	110.88 (10)	C28—C23—C24	118.28 (12)
N1—C2—C3	111.35 (9)	C28—C23—C22	123.04 (12)
C21—C2—C3	108.83 (10)	C24—C23—C22	118.68 (12)
C4—C3—C2	116.02 (10)	C25—C24—C23	121.02 (13)
O1—C4—C3	108.10 (10)	C26—C25—C24	119.93 (14)
O1—C4—C5	108.78 (10)	C27—C26—C25	119.75 (13)
C3—C4—C5	115.01 (10)	C26—C27—C28	120.53 (13)
C5A—C5—C4	117.65 (10)	C27—C28—C23	120.48 (13)
C7—C6—C5A	119.61 (12)	C6—C5A—C9A	118.76 (11)
F1—C7—C8	118.75 (12)	C6—C5A—C5	118.63 (11)
F1—C7—C6	118.32 (12)	C9A—C5A—C5	122.40 (11)
C8—C7—C6	122.92 (12)	C9—C9A—C5A	119.82 (11)
C7—C8—C9	117.54 (12)	C9—C9A—N1	119.24 (11)
C8—C9—C9A	121.33 (12)	C5A—C9A—N1	120.71 (11)
C22—C21—C2	126.64 (11)

C9A—N1—C2—C21	−154.56 (10)	C22—C23—C24—C25	−179.08 (13)
C9A—N1—C2—C3	84.10 (12)	C23—C24—C25—C26	−0.7 (2)
N1—C2—C3—C4	−65.54 (13)	C24—C25—C26—C27	−0.4 (2)
C21—C2—C3—C4	171.93 (10)	C25—C26—C27—C28	0.7 (2)
C2—C3—C4—O1	−177.68 (9)	C26—C27—C28—C23	0.1 (2)
C2—C3—C4—C5	60.58 (14)	C24—C23—C28—C27	−1.1 (2)
O1—C4—C5—C5A	168.01 (10)	C22—C23—C28—C27	179.41 (12)
C3—C4—C5—C5A	−70.62 (14)	C7—C6—C5A—C9A	1.06 (18)
C5A—C6—C7—F1	−179.62 (12)	C7—C6—C5A—C5	−173.82 (12)
C5A—C6—C7—C8	0.2 (2)	C4—C5—C5A—C6	−126.84 (12)
F1—C7—C8—C9	178.58 (12)	C4—C5—C5A—C9A	58.48 (16)
C6—C7—C8—C9	−1.3 (2)	C8—C9—C9A—C5A	0.20 (18)
C7—C8—C9—C9A	1.04 (19)	C8—C9—C9A—N1	174.73 (11)
N1—C2—C21—C22	−6.00 (17)	C6—C5A—C9A—C9	−1.26 (17)
C3—C2—C21—C22	116.81 (14)	C5—C5A—C9A—C9	173.41 (11)
C2—C21—C22—C23	−178.19 (12)	C6—C5A—C9A—N1	−175.70 (11)
C21—C22—C23—C28	−11.9 (2)	C5—C5A—C9A—N1	−1.03 (17)
C21—C22—C23—C24	168.68 (13)	C2—N1—C9A—C9	120.88 (12)
C28—C23—C24—C25	1.4 (2)	C2—N1—C9A—C5A	−64.65 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.904 (17)	2.450 (16)	3.2709 (14)	151 (13)
O1—H1O···N1ⁱⁱ	0.88 (2)	2.14 (2)	3.0187 (14)	172.9 (16)
C5—H5A···N1ⁱⁱ	0.99	2.67	3.3657 (16)	128
C6—H6···F1ⁱⁱⁱ	0.95	2.47	3.4236 (16)	177
C5—H5A···O1^iv	0.99	2.53	3.4027 (15)	148

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

(Compound_5a) 7-Fluoro-cis-2-[(E)-pent-1-enyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol top

Crystal data top

C₁₅H₂₀FNO	D_x = 1.207 Mg m⁻³
M_r = 249.32	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3:H	Cell parameters from 9421 reflections
a = 25.119 (2) Å	θ = 2.8–22.2°
c = 11.2812 (12) Å	µ = 0.08 mm⁻¹
V = 6164.2 (12) Å³	T = 298 K
Z = 18	Parallelepiped, less
F(000) = 2412	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	2024 reflections with I > 2σ(I)
π and ω scans	R_int = 0.036
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 26.4°, θ_min = 2.6°
T_min = 0.68, T_max = 0.74	h = −31→31
34372 measured reflections	k = −31→26
2814 independent reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: mixed
wR(F²) = 0.229	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1155P)² + 11.0098P] where P = (F_o² + 2F_c²)/3
2814 reflections	(Δ/σ)_max < 0.001
212 parameters	Δρ_max = 0.55 e Å⁻³
159 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₅H₂₀FNO	Z = 18
M_r = 249.32	Mo Kα radiation
Trigonal, R3:H	µ = 0.08 mm⁻¹
a = 25.119 (2) Å	T = 298 K
c = 11.2812 (12) Å	0.30 × 0.25 × 0.20 mm
V = 6164.2 (12) Å³

Data collection top

Bruker Kappa APEXII diffractometer	2814 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	2024 reflections with I > 2σ(I)
T_min = 0.68, T_max = 0.74	R_int = 0.036
34372 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	159 restraints
wR(F²) = 0.229	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1155P)² + 11.0098P] where P = (F_o² + 2F_c²)/3
2814 reflections	Δρ_max = 0.55 e Å⁻³
212 parameters	Δρ_min = −0.41 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.44770 (10)	0.47721 (10)	0.65896 (18)	0.0460 (5)
F1	0.53114 (10)	0.41476 (10)	1.06076 (18)	0.0891 (7)
C2	0.39810 (12)	0.49241 (11)	0.6739 (2)	0.0480 (6)
C3	0.33455 (11)	0.43494 (12)	0.6811 (2)	0.0494 (6)
H3A	0.3041	0.4480	0.6832	0.059*
H3B	0.3279	0.4116	0.6087	0.059*
H1N	0.4810 (14)	0.5102 (14)	0.634 (3)	0.062 (8)*
C4	0.32254 (10)	0.39220 (11)	0.7848 (2)	0.0448 (6)
H4	0.3283	0.4148	0.8589	0.054*
H2	0.4062 (13)	0.5176 (13)	0.745 (3)	0.054 (7)*
C5	0.36406 (11)	0.36420 (11)	0.7852 (2)	0.0454 (6)
H5A	0.3460	0.3285	0.8366	0.055*
H5B	0.3653	0.3502	0.7057	0.055*
C6	0.45135 (13)	0.39216 (12)	0.9261 (2)	0.0530 (6)
H6	0.4260	0.3566	0.9687	0.064*
C7	0.51085 (14)	0.43021 (14)	0.9618 (3)	0.0616 (7)
O7	0.25956 (8)	0.34478 (9)	0.77523 (17)	0.0593 (6)
H7O	0.2424 (9)	0.3368 (13)	0.846 (3)	0.089*
C8	0.54992 (14)	0.48273 (15)	0.9022 (3)	0.0675 (8)
H8	0.5902	0.5076	0.9276	0.081*
C9	0.52822 (12)	0.49807 (13)	0.8031 (3)	0.0566 (7)
H9	0.5542	0.5338	0.7616	0.068*
C10A	0.39929 (15)	0.53013 (13)	0.5698 (3)	0.0644 (11)	0.483 (5)
H10A	0.4025	0.5136	0.4981	0.077*	0.483 (5)
C11A	0.3970 (8)	0.5805 (5)	0.5554 (10)	0.089 (3)	0.483 (5)
H11A	0.3990	0.6020	0.6241	0.107*	0.483 (5)
C12A	0.3909 (5)	0.6096 (6)	0.4329 (11)	0.118 (3)	0.483 (5)
H12A	0.3870	0.6455	0.4493	0.141*	0.483 (5)
H12B	0.3542	0.5798	0.3912	0.141*	0.483 (5)
C13A	0.4515 (6)	0.6295 (6)	0.3498 (9)	0.115 (3)	0.483 (5)
H13A	0.4899	0.6515	0.3932	0.138*	0.483 (5)
H13B	0.4497	0.5951	0.3070	0.138*	0.483 (5)
C14A	0.4386 (9)	0.6712 (6)	0.2717 (14)	0.148 (5)	0.483 (5)
H14A	0.4390	0.6607	0.1900	0.222*	0.483 (5)
H14B	0.4697	0.7132	0.2848	0.222*	0.483 (5)
H14C	0.3990	0.6658	0.2912	0.222*	0.483 (5)
C10B	0.39929 (15)	0.53013 (13)	0.5698 (3)	0.0644 (11)	0.517 (5)
H10B	0.3975	0.5162	0.4927	0.077*	0.517 (5)
C11B	0.4029 (7)	0.5829 (4)	0.5902 (8)	0.078 (2)	0.517 (5)
H11B	0.4047	0.5958	0.6682	0.094*	0.517 (5)
C12B	0.4042 (4)	0.6253 (4)	0.4865 (7)	0.096 (2)	0.517 (5)
H12C	0.4381	0.6667	0.4994	0.115*	0.517 (5)
H12D	0.3664	0.6270	0.4885	0.115*	0.517 (5)
C13B	0.4115 (6)	0.6019 (5)	0.3546 (8)	0.112 (3)	0.517 (5)
H13C	0.4457	0.5943	0.3592	0.134*	0.517 (5)
H13D	0.3749	0.5624	0.3410	0.134*	0.517 (5)
C14B	0.4214 (8)	0.6408 (6)	0.2428 (13)	0.150 (4)	0.517 (5)
H14D	0.4142	0.6159	0.1736	0.224*	0.517 (5)
H14E	0.4629	0.6746	0.2416	0.224*	0.517 (5)
H14F	0.3934	0.6563	0.2435	0.224*	0.517 (5)
C5A	0.42899 (11)	0.40696 (11)	0.8254 (2)	0.0435 (6)
C9A	0.46799 (11)	0.46087 (11)	0.7641 (2)	0.0438 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0457 (11)	0.0416 (11)	0.0437 (11)	0.0167 (9)	0.0038 (9)	0.0029 (9)
F1	0.0927 (14)	0.1043 (15)	0.0805 (13)	0.0569 (12)	−0.0324 (11)	0.0035 (11)
C2	0.0540 (14)	0.0443 (13)	0.0463 (14)	0.0251 (11)	−0.0033 (11)	0.0000 (10)
C3	0.0476 (13)	0.0537 (14)	0.0480 (14)	0.0262 (11)	−0.0002 (10)	0.0032 (11)
C4	0.0407 (12)	0.0495 (13)	0.0398 (12)	0.0192 (10)	0.0006 (9)	−0.0003 (10)
C5	0.0478 (13)	0.0412 (12)	0.0418 (13)	0.0181 (10)	0.0012 (10)	0.0027 (9)
C6	0.0587 (15)	0.0557 (15)	0.0513 (15)	0.0337 (13)	−0.0018 (12)	0.0029 (12)
C7	0.0658 (17)	0.0717 (18)	0.0590 (17)	0.0430 (16)	−0.0138 (14)	−0.0040 (14)
O7	0.0418 (9)	0.0710 (12)	0.0495 (11)	0.0166 (9)	0.0016 (8)	0.0092 (9)
C8	0.0541 (16)	0.0657 (18)	0.081 (2)	0.0289 (14)	−0.0206 (15)	−0.0135 (16)
C9	0.0488 (14)	0.0485 (14)	0.0675 (18)	0.0205 (11)	−0.0045 (12)	−0.0019 (12)
C10A	0.069 (2)	0.0536 (17)	0.0644 (19)	0.0259 (15)	−0.0082 (15)	0.0126 (14)
C11A	0.093 (4)	0.084 (4)	0.095 (5)	0.047 (3)	−0.015 (4)	0.024 (3)
C12A	0.120 (4)	0.103 (4)	0.116 (5)	0.045 (3)	−0.017 (4)	0.013 (4)
C13A	0.119 (5)	0.110 (4)	0.102 (4)	0.046 (4)	−0.025 (4)	0.022 (4)
C14A	0.156 (8)	0.126 (8)	0.134 (8)	0.049 (7)	−0.023 (6)	0.024 (6)
C10B	0.069 (2)	0.0536 (17)	0.0644 (19)	0.0259 (15)	−0.0082 (15)	0.0126 (14)
C11B	0.083 (4)	0.074 (3)	0.078 (4)	0.040 (3)	−0.015 (4)	0.021 (3)
C12B	0.113 (4)	0.080 (3)	0.092 (4)	0.046 (3)	−0.035 (3)	0.022 (3)
C13B	0.120 (5)	0.107 (4)	0.087 (4)	0.040 (4)	−0.013 (4)	0.019 (4)
C14B	0.175 (9)	0.125 (8)	0.137 (6)	0.066 (7)	0.002 (7)	0.042 (6)
C5A	0.0465 (12)	0.0452 (12)	0.0430 (12)	0.0260 (10)	0.0003 (10)	−0.0019 (10)
C9A	0.0464 (13)	0.0418 (12)	0.0451 (13)	0.0235 (10)	0.0003 (10)	−0.0034 (10)

Geometric parameters (Å, º) top

N1—C9A	1.430 (3)	C7—C8	1.365 (5)
N1—C2	1.484 (3)	C8—C9	1.380 (4)
F1—C7	1.361 (3)	C9—C9A	1.393 (4)
C2—C10A	1.500 (4)	C10A—C11A	1.306 (5)
C2—C3	1.528 (4)	C11A—C12A	1.606 (10)
C3—C4	1.512 (3)	C12A—C13A	1.639 (11)
C4—O7	1.431 (3)	C13A—C14A	1.522 (11)
C4—C5	1.522 (3)	C11B—C12B	1.572 (8)
C5—C5A	1.506 (3)	C12B—C13B	1.645 (10)
C6—C7	1.372 (4)	C13B—C14B	1.537 (10)
C6—C5A	1.398 (4)	C5A—C9A	1.395 (3)

C9A—N1—C2	116.44 (19)	C8—C9—C9A	121.1 (3)
N1—C2—C10A	108.6 (2)	C11A—C10A—C2	135.5 (6)
N1—C2—C3	112.2 (2)	C10A—C11A—C12A	127.5 (10)
C10A—C2—C3	108.6 (2)	C11A—C12A—C13A	110.2 (10)
C4—C3—C2	117.1 (2)	C14A—C13A—C12A	93.2 (11)
O7—C4—C3	106.11 (19)	C11B—C12B—C13B	113.5 (7)
O7—C4—C5	110.1 (2)	C14B—C13B—C12B	121.7 (10)
C3—C4—C5	113.0 (2)	C9A—C5A—C6	118.7 (2)
C5A—C5—C4	114.8 (2)	C9A—C5A—C5	121.8 (2)
C7—C6—C5A	119.8 (3)	C6—C5A—C5	119.4 (2)
F1—C7—C8	119.3 (3)	C9—C9A—C5A	119.6 (2)
F1—C7—C6	118.4 (3)	C9—C9A—N1	119.5 (2)
C8—C7—C6	122.3 (3)	C5A—C9A—N1	120.8 (2)
C7—C8—C9	118.4 (3)

C9A—N1—C2—C10A	158.9 (2)	C10A—C11A—C12A—C13A	−63.7 (19)
C9A—N1—C2—C3	−81.0 (3)	C11A—C12A—C13A—C14A	−162.5 (10)
N1—C2—C3—C4	63.2 (3)	C11B—C12B—C13B—C14B	−172.6 (12)
C10A—C2—C3—C4	−176.7 (2)	C7—C6—C5A—C9A	−0.6 (4)
C2—C3—C4—O7	176.5 (2)	C7—C6—C5A—C5	178.6 (2)
C2—C3—C4—C5	−62.8 (3)	C4—C5—C5A—C9A	−62.1 (3)
O7—C4—C5—C5A	−165.3 (2)	C4—C5—C5A—C6	118.6 (2)
C3—C4—C5—C5A	76.3 (3)	C8—C9—C9A—C5A	−0.5 (4)
C5A—C6—C7—F1	179.5 (2)	C8—C9—C9A—N1	−178.0 (3)
C5A—C6—C7—C8	−0.2 (4)	C6—C5A—C9A—C9	1.0 (4)
F1—C7—C8—C9	−179.1 (3)	C5—C5A—C9A—C9	−178.3 (2)
C6—C7—C8—C9	0.7 (5)	C6—C5A—C9A—N1	178.5 (2)
C7—C8—C9—C9A	−0.3 (5)	C5—C5A—C9A—N1	−0.8 (3)
N1—C2—C10A—C11A	−133.6 (11)	C2—N1—C9A—C9	−116.0 (3)
C3—C2—C10A—C11A	104.1 (12)	C2—N1—C9A—C5A	66.5 (3)
C2—C10A—C11A—C12A	−172.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O7ⁱ	0.88 (3)	2.49 (3)	3.356 (3)	171 (3)
O7—H7O···N1ⁱⁱ	0.88	2.02	2.889 (3)	169
C9—H9···O7ⁱ	0.93	2.63	3.451 (4)	147

Symmetry codes: (i) x−y+2/3, x+1/3, −z+4/3; (ii) −y+2/3, x−y+1/3, z+1/3.

(Compound_5b) 7-Fluoro-cis-2-[(E)-pent-1-enyl]-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol top

Crystal data top

C₁₅H₂₀FNO	D_x = 1.262 Mg m⁻³
M_r = 249.32	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3:H	Cell parameters from 9791 reflections
a = 49.395 (2) Å	θ = 2.9–27.4°
c = 11.1802 (5) Å	µ = 0.09 mm⁻¹
V = 23623 (2) Å³	T = 100 K
Z = 72	Parallelepiped, less
F(000) = 9648	0.30 × 0.25 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	8771 reflections with I > 2σ(I)
π and ω scans	R_int = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2006)	θ_max = 27.5°, θ_min = 1.4°
T_min = 0.89, T_max = 0.98	h = −62→62
124259 measured reflections	k = −63→64
12035 independent reflections	l = −14→13

Refinement top

Refinement on F²	459 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.048P)² + 28.8932P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
12035 reflections	Δρ_max = 0.44 e Å⁻³
786 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₂₀FNO	Z = 72
M_r = 249.32	Mo Kα radiation
Trigonal, R3:H	µ = 0.09 mm⁻¹
a = 49.395 (2) Å	T = 100 K
c = 11.1802 (5) Å	0.30 × 0.25 × 0.20 mm
V = 23623 (2) Å³

Data collection top

Bruker Kappa APEXII diffractometer	12035 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	8771 reflections with I > 2σ(I)
T_min = 0.89, T_max = 0.98	R_int = 0.043
124259 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	459 restraints
wR(F²) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.048P)² + 28.8932P] where P = (F_o² + 2F_c²)/3
12035 reflections	Δρ_max = 0.44 e Å⁻³
786 parameters	Δρ_min = −0.28 e Å⁻³

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N11	0.34466 (3)	0.40532 (3)	1.00064 (10)	0.0169 (2)
F11	0.27312 (2)	0.37140 (2)	0.58610 (7)	0.0270 (2)
C411	0.29720 (4)	0.59163 (4)	0.57416 (16)	0.0377 (4)	0.319 (8)
H11C	0.2986	0.6002	0.6516	0.045*	0.319 (8)
C412	0.2953 (3)	0.6093 (3)	0.4671 (7)	0.0305 (11)	0.319 (8)
H12E	0.2812	0.6174	0.4885	0.037*	0.319 (8)
H12F	0.3163	0.6276	0.4544	0.037*	0.319 (8)
C413	0.2844 (2)	0.59265 (19)	0.3497 (7)	0.0308 (13)	0.319 (8)
H13E	0.2641	0.5732	0.3605	0.037*	0.319 (8)
H13F	0.2997	0.5870	0.3196	0.037*	0.319 (8)
C414	0.28076 (17)	0.61383 (14)	0.2595 (6)	0.0300 (14)	0.319 (8)
H14G	0.2715	0.6021	0.1857	0.045*	0.319 (8)
H14H	0.3013	0.6319	0.2419	0.045*	0.319 (8)
H14I	0.2672	0.6211	0.2931	0.045*	0.319 (8)
C415	0.29720 (4)	0.59163 (4)	0.57416 (16)	0.0377 (4)	0.341 (3)
H15	0.2921	0.5936	0.6545	0.045*	0.341 (3)
C416	0.30233 (12)	0.62061 (12)	0.5067 (5)	0.0299 (9)	0.341 (3)
H16A	0.2848	0.6245	0.5204	0.036*	0.341 (3)
H16B	0.3220	0.6393	0.5323	0.036*	0.341 (3)
C417	0.30403 (10)	0.61315 (11)	0.3761 (4)	0.0273 (9)	0.341 (3)
H17A	0.3190	0.6054	0.3676	0.033*	0.341 (3)
H17B	0.3120	0.6325	0.3283	0.033*	0.341 (3)
C418	0.27235 (13)	0.58869 (13)	0.3269 (5)	0.0323 (12)	0.341 (3)
H18A	0.2744	0.5854	0.2416	0.048*	0.341 (3)
H18B	0.2573	0.5959	0.3374	0.048*	0.341 (3)
H18C	0.2650	0.5690	0.3700	0.048*	0.341 (3)
C419	0.29720 (4)	0.59163 (4)	0.57416 (16)	0.0377 (4)	0.340 (8)
H19A	0.2981	0.6011	0.6492	0.045*	0.340 (8)
C420	0.2958 (3)	0.6069 (2)	0.4514 (7)	0.0306 (11)	0.340 (8)
H20A	0.2784	0.6112	0.4580	0.037*	0.340 (8)
H20B	0.3153	0.6274	0.4463	0.037*	0.340 (8)
C421	0.29209 (17)	0.59085 (15)	0.3319 (6)	0.0289 (11)	0.340 (8)
H21A	0.2725	0.5704	0.3329	0.035*	0.340 (8)
H21B	0.3097	0.5870	0.3204	0.035*	0.340 (8)
C422	0.29106 (17)	0.61025 (12)	0.2260 (6)	0.0293 (14)	0.340 (8)
H22A	0.2890	0.5991	0.1511	0.044*	0.340 (8)
H22B	0.3104	0.6306	0.2244	0.044*	0.340 (8)
H22C	0.2731	0.6134	0.2352	0.044*	0.340 (8)
C410	0.29701 (4)	0.56496 (4)	0.56497 (14)	0.0307 (4)
C49A	0.26156 (3)	0.49464 (3)	0.76169 (12)	0.0185 (3)
C49	0.23086 (3)	0.48294 (3)	0.80082 (13)	0.0224 (3)
H9C	0.2175	0.4883	0.7585	0.027*
C48	0.21945 (3)	0.46363 (3)	0.90032 (14)	0.0254 (3)
H8C	0.1985	0.4555	0.9261	0.030*
H2O	0.2841 (4)	0.4991 (5)	0.5109 (18)	0.050 (6)*
C47	0.23945 (3)	0.45664 (3)	0.96036 (13)	0.0240 (3)
H3O	0.3292 (4)	0.4518 (4)	0.1705 (17)	0.041 (5)*
C46	0.26982 (3)	0.46764 (3)	0.92451 (12)	0.0205 (3)
H6C	0.2829	0.4622	0.9683	0.025*
H1O	0.3815 (4)	0.3372 (4)	0.8117 (17)	0.043 (5)*
C45A	0.28138 (3)	0.48676 (3)	0.82365 (12)	0.0178 (3)
H4O	0.3758 (4)	0.5448 (4)	0.8477 (18)	0.044 (5)*
C45	0.31449 (3)	0.49801 (3)	0.78342 (12)	0.0175 (3)
H5CA	0.3139	0.4901	0.7016	0.021*
H5CB	0.3238	0.4889	0.8367	0.021*
C44	0.33575 (3)	0.53372 (3)	0.78294 (12)	0.0178 (3)
H4C	0.3324	0.5425	0.8585	0.021*
H2N	0.3134 (4)	0.4083 (4)	0.2895 (14)	0.026 (4)*
C43	0.32988 (3)	0.54921 (3)	0.67663 (12)	0.0195 (3)
H3CA	0.3329	0.5401	0.6026	0.023*
H3CB	0.3459	0.5717	0.6772	0.023*
H1N	0.3431 (3)	0.4215 (4)	1.0311 (14)	0.023 (4)*
C42	0.29770 (3)	0.54646 (3)	0.67063 (12)	0.0197 (3)
H2C	0.2941	0.5553	0.7455	0.024*
H10C	0.2965 (4)	0.5564 (4)	0.4860 (17)	0.045 (5)*
H3N	0.4201 (4)	0.5736 (4)	−0.0348 (14)	0.027 (4)*
H4N	0.2554 (4)	0.5138 (4)	0.6247 (14)	0.024 (4)*
O11	0.37855 (2)	0.34202 (2)	0.88342 (9)	0.0209 (2)
N21	0.31433 (3)	0.42554 (3)	0.31909 (10)	0.0169 (2)
F21	0.39145 (2)	0.45825 (2)	0.71821 (7)	0.0300 (2)
O21	0.28801 (2)	0.49469 (2)	0.43828 (9)	0.0223 (2)
C22	0.28152 (3)	0.41842 (3)	0.34093 (11)	0.0173 (3)
H2B	0.2741	0.4072	0.4191	0.021*
C12	0.37836 (3)	0.41447 (3)	0.99245 (12)	0.0174 (3)
H2A	0.3879	0.4283	0.9212	0.021*
N31	0.40300 (3)	0.55637 (3)	−0.00756 (10)	0.0185 (2)
F31	0.37125 (2)	0.59685 (2)	0.40456 (8)	0.0333 (2)
O31	0.33407 (2)	0.45989 (2)	0.09972 (9)	0.0210 (2)
N41	0.27191 (3)	0.51345 (3)	0.65589 (10)	0.0193 (2)
F41	0.22883 (2)	0.43795 (2)	1.05925 (8)	0.0328 (2)
O41	0.36780 (2)	0.54157 (2)	0.77562 (9)	0.0221 (2)
C23	0.27900 (3)	0.44792 (3)	0.34420 (12)	0.0187 (3)
H3BA	0.2877	0.4595	0.2686	0.022*
H3BB	0.2566	0.4416	0.3467	0.022*
C13	0.38308 (3)	0.38618 (3)	0.98311 (12)	0.0181 (3)
H3A	0.4058	0.3939	0.9826	0.022*
H3B	0.3744	0.3734	1.0564	0.022*
C32	0.40991 (3)	0.53030 (3)	0.00136 (12)	0.0186 (3)
H2D	0.4223	0.5330	0.0758	0.022*
C24	0.29539 (3)	0.47014 (3)	0.44786 (12)	0.0185 (3)
H4B	0.2869	0.4587	0.5249	0.022*
C14	0.36875 (3)	0.36484 (3)	0.87580 (11)	0.0175 (3)
H14	0.3773	0.3773	0.8008	0.021*
C33	0.38020 (3)	0.49827 (3)	0.00420 (12)	0.0181 (3)
H3DA	0.3681	0.4960	−0.0695	0.022*
H3DB	0.3864	0.4820	0.0019	0.022*
C34	0.35875 (3)	0.49174 (3)	0.11100 (12)	0.0180 (3)
H4D	0.3707	0.4941	0.1863	0.022*
C25	0.33097 (3)	0.48406 (3)	0.44610 (12)	0.0184 (3)
H5BA	0.3386	0.4912	0.3638	0.022*
H5BB	0.3406	0.5026	0.4988	0.022*
C15	0.33288 (3)	0.34862 (3)	0.87380 (12)	0.0176 (3)
H15A	0.3247	0.3300	0.8215	0.021*
H15B	0.3249	0.3413	0.9556	0.021*
C35	0.34482 (3)	0.51345 (3)	0.11627 (12)	0.0183 (3)
H5DA	0.3377	0.5150	0.0351	0.022*
H5DB	0.3262	0.5038	0.1688	0.022*
C35A	0.36701 (3)	0.54597 (3)	0.16138 (12)	0.0187 (3)
C25A	0.34204 (3)	0.46199 (3)	0.48536 (11)	0.0176 (3)
C15A	0.32065 (3)	0.36931 (3)	0.83032 (11)	0.0166 (3)
C16	0.30230 (3)	0.36121 (3)	0.72687 (11)	0.0185 (3)
H6A	0.2976	0.3427	0.6843	0.022*
C17	0.29108 (3)	0.38009 (3)	0.68695 (12)	0.0204 (3)
C36	0.35949 (3)	0.55690 (3)	0.26442 (12)	0.0216 (3)
H6D	0.3407	0.5437	0.3067	0.026*
C26	0.36144 (3)	0.46957 (3)	0.58553 (12)	0.0205 (3)
H6B	0.3671	0.4881	0.6294	0.025*
C18	0.29731 (3)	0.40719 (3)	0.74472 (12)	0.0218 (3)
H8A	0.2893	0.4199	0.7154	0.026*
C37	0.37940 (3)	0.58679 (4)	0.30412 (13)	0.0253 (3)
C27	0.37238 (3)	0.45005 (3)	0.62031 (12)	0.0224 (3)
C19	0.31558 (3)	0.41541 (3)	0.84723 (12)	0.0199 (3)
H9A	0.3202	0.4341	0.8884	0.024*
C38	0.40681 (3)	0.60682 (3)	0.24662 (13)	0.0269 (3)
H8D	0.4201	0.6274	0.2757	0.032*
C28	0.36511 (3)	0.42299 (3)	0.56027 (12)	0.0219 (3)
H8B	0.3732	0.4101	0.5855	0.026*
C19A	0.32728 (3)	0.39686 (3)	0.89089 (11)	0.0168 (3)
C39	0.41454 (3)	0.59611 (3)	0.14481 (13)	0.0235 (3)
H9D	0.4335	0.6095	0.1040	0.028*
C29	0.34556 (3)	0.41512 (3)	0.46162 (12)	0.0199 (3)
H9B	0.3400	0.3964	0.4193	0.024*
C110	0.39442 (3)	0.43229 (3)	1.10426 (12)	0.0183 (3)
H10A	0.3848	0.4236	1.1790	0.022*
C29A	0.33387 (3)	0.43422 (3)	0.42330 (11)	0.0169 (3)
C111	0.42101 (3)	0.45923 (3)	1.10490 (12)	0.0207 (3)
H11A	0.4297	0.4681	1.0292	0.025*
C39A	0.39492 (3)	0.56594 (3)	0.10127 (12)	0.0188 (3)
C210	0.26079 (3)	0.39767 (3)	0.24270 (12)	0.0188 (3)
H10B	0.2658	0.4047	0.1624	0.023*
C112	0.43889 (3)	0.47726 (3)	1.21326 (12)	0.0240 (3)
H12A	0.4428	0.4989	1.2061	0.029*
H12B	0.4595	0.4784	1.2130	0.029*
C211	0.23589 (3)	0.37001 (3)	0.26272 (12)	0.0201 (3)
H11B	0.2329	0.3628	0.3430	0.024*
C113	0.42333 (3)	0.46421 (3)	1.33300 (12)	0.0259 (3)
H13A	0.4198	0.4428	1.3426	0.031*
H13B	0.4027	0.4630	1.3347	0.031*
C212	0.21183 (3)	0.34868 (3)	0.17418 (12)	0.0226 (3)
H12C	0.1918	0.3476	0.1937	0.027*
H12D	0.2087	0.3274	0.1851	0.027*
C114	0.44315 (4)	0.48443 (4)	1.43649 (13)	0.0292 (3)
H14A	0.4325	0.4752	1.5123	0.044*
H14B	0.4462	0.5055	1.4285	0.044*
H14C	0.4635	0.4856	1.4354	0.044*
C310	0.42927 (3)	0.53233 (3)	−0.10552 (13)	0.0246 (3)	0.841 (2)
H10D	0.4221	0.5336	−0.1831	0.029*	0.841 (2)
C311	0.45638 (4)	0.53238 (5)	−0.09460 (18)	0.0219 (4)	0.841 (2)
H11D	0.4627	0.5306	−0.0161	0.026*	0.841 (2)
C312	0.47778 (4)	0.53507 (4)	−0.19651 (14)	0.0243 (4)	0.841 (2)
H12G	0.4996	0.5496	−0.1717	0.029*	0.841 (2)
H12H	0.4758	0.5143	−0.2089	0.029*	0.841 (2)
C313	0.47219 (4)	0.54616 (4)	−0.31500 (14)	0.0263 (4)	0.841 (2)
H13G	0.4730	0.5664	−0.3036	0.032*	0.841 (2)
H13H	0.4511	0.5309	−0.3448	0.032*	0.841 (2)
C314	0.49656 (6)	0.55001 (8)	−0.4072 (2)	0.0279 (6)	0.841 (2)
H14J	0.4935	0.5590	−0.4806	0.042*	0.841 (2)
H14K	0.4943	0.5296	−0.4249	0.042*	0.841 (2)
H14L	0.5175	0.5640	−0.3753	0.042*	0.841 (2)
C315	0.42927 (3)	0.53233 (3)	−0.10552 (13)	0.0246 (3)	0.159 (2)
H15C	0.4233	0.5396	−0.1737	0.029*	0.159 (2)
C316	0.4522 (2)	0.5269 (3)	−0.1319 (8)	0.0275 (17)	0.159 (2)
H16C	0.4632	0.5234	−0.0696	0.033*	0.159 (2)
C317	0.46092 (17)	0.5261 (2)	−0.2607 (7)	0.0246 (13)	0.159 (2)
H17C	0.4478	0.5308	−0.3144	0.030*	0.159 (2)
H17D	0.4576	0.5051	−0.2810	0.030*	0.159 (2)
C318	0.49498 (18)	0.5505 (2)	−0.2755 (8)	0.0315 (16)	0.159 (2)
H18D	0.5077	0.5469	−0.2157	0.038*	0.159 (2)
H18E	0.4978	0.5715	−0.2617	0.038*	0.159 (2)
C319	0.5060 (4)	0.5487 (5)	−0.4001 (9)	0.032 (3)	0.159 (2)
H19D	0.5044	0.5283	−0.4116	0.049*	0.159 (2)
H19E	0.5277	0.5653	−0.4102	0.049*	0.159 (2)
H19F	0.4928	0.5514	−0.4592	0.049*	0.159 (2)
C214	0.24464 (4)	0.35197 (4)	−0.00572 (13)	0.0307 (4)
H14D	0.2478	0.3573	−0.0909	0.046*
H14E	0.2385	0.3299	0.0048	0.046*
H14F	0.2641	0.3652	0.0380	0.046*
C213	0.21896 (3)	0.35743 (3)	0.04241 (13)	0.0248 (3)
H13C	0.1997	0.3449	−0.0050	0.030*
H13D	0.2254	0.3798	0.0322	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N11	0.0186 (6)	0.0182 (6)	0.0144 (5)	0.0096 (5)	−0.0010 (4)	−0.0021 (4)
F11	0.0271 (4)	0.0340 (5)	0.0193 (4)	0.0148 (4)	−0.0085 (3)	−0.0012 (4)
C411	0.0301 (7)	0.0378 (7)	0.0467 (8)	0.0181 (6)	0.0053 (6)	0.0203 (6)
C412	0.0296 (15)	0.0302 (15)	0.0358 (15)	0.0181 (13)	0.0027 (14)	0.0090 (13)
C413	0.030 (2)	0.0295 (17)	0.0336 (17)	0.0154 (15)	−0.0001 (17)	0.0063 (15)
C414	0.030 (3)	0.036 (2)	0.027 (2)	0.018 (2)	0.002 (2)	0.0070 (19)
C415	0.0301 (7)	0.0378 (7)	0.0467 (8)	0.0181 (6)	0.0053 (6)	0.0203 (6)
C416	0.0289 (15)	0.0305 (15)	0.0327 (15)	0.0167 (12)	0.0035 (13)	0.0080 (13)
C417	0.0280 (15)	0.0272 (15)	0.0289 (15)	0.0155 (12)	0.0036 (13)	0.0020 (13)
C418	0.031 (2)	0.035 (2)	0.032 (2)	0.0180 (19)	0.0005 (19)	0.0049 (17)
C419	0.0301 (7)	0.0378 (7)	0.0467 (8)	0.0181 (6)	0.0053 (6)	0.0203 (6)
C420	0.0308 (15)	0.0290 (15)	0.0352 (15)	0.0174 (12)	0.0023 (14)	0.0081 (13)
C421	0.0294 (18)	0.0279 (16)	0.0314 (16)	0.0158 (14)	0.0002 (15)	0.0069 (14)
C422	0.032 (3)	0.027 (2)	0.028 (2)	0.0147 (18)	−0.001 (2)	0.0059 (18)
C410	0.0285 (8)	0.0486 (10)	0.0239 (8)	0.0259 (8)	0.0086 (6)	0.0161 (7)
C49A	0.0208 (7)	0.0175 (7)	0.0174 (7)	0.0096 (6)	−0.0010 (5)	−0.0049 (5)
C49	0.0203 (7)	0.0235 (7)	0.0254 (7)	0.0123 (6)	−0.0017 (6)	−0.0039 (6)
C48	0.0193 (7)	0.0215 (7)	0.0328 (8)	0.0082 (6)	0.0059 (6)	−0.0010 (6)
C47	0.0274 (8)	0.0181 (7)	0.0234 (7)	0.0091 (6)	0.0057 (6)	0.0023 (6)
C46	0.0224 (7)	0.0174 (7)	0.0213 (7)	0.0096 (6)	−0.0011 (6)	−0.0020 (5)
C45A	0.0184 (7)	0.0154 (6)	0.0181 (7)	0.0072 (5)	−0.0016 (5)	−0.0046 (5)
C45	0.0187 (7)	0.0186 (7)	0.0164 (6)	0.0102 (6)	−0.0013 (5)	−0.0018 (5)
C44	0.0179 (7)	0.0194 (7)	0.0148 (6)	0.0082 (6)	−0.0011 (5)	−0.0005 (5)
C43	0.0213 (7)	0.0196 (7)	0.0166 (7)	0.0095 (6)	−0.0015 (5)	0.0008 (5)
C42	0.0249 (7)	0.0222 (7)	0.0151 (6)	0.0141 (6)	0.0015 (5)	0.0019 (5)
O11	0.0280 (5)	0.0257 (5)	0.0157 (5)	0.0184 (5)	−0.0018 (4)	−0.0022 (4)
N21	0.0177 (6)	0.0181 (6)	0.0151 (5)	0.0090 (5)	−0.0021 (4)	−0.0037 (5)
F21	0.0293 (5)	0.0378 (5)	0.0230 (4)	0.0168 (4)	−0.0125 (4)	−0.0041 (4)
O21	0.0270 (5)	0.0275 (5)	0.0181 (5)	0.0178 (5)	−0.0031 (4)	−0.0062 (4)
C22	0.0164 (6)	0.0189 (7)	0.0143 (6)	0.0071 (5)	0.0000 (5)	−0.0008 (5)
C12	0.0161 (6)	0.0172 (7)	0.0156 (6)	0.0058 (5)	0.0000 (5)	0.0011 (5)
N31	0.0185 (6)	0.0178 (6)	0.0163 (6)	0.0069 (5)	0.0011 (5)	0.0011 (5)
F31	0.0363 (5)	0.0374 (5)	0.0286 (5)	0.0202 (4)	−0.0018 (4)	−0.0149 (4)
O31	0.0231 (5)	0.0174 (5)	0.0166 (5)	0.0056 (4)	0.0019 (4)	0.0003 (4)
N41	0.0193 (6)	0.0261 (6)	0.0153 (6)	0.0134 (5)	−0.0032 (5)	−0.0024 (5)
F41	0.0324 (5)	0.0291 (5)	0.0334 (5)	0.0127 (4)	0.0128 (4)	0.0121 (4)
O41	0.0174 (5)	0.0274 (5)	0.0176 (5)	0.0084 (4)	−0.0026 (4)	0.0032 (4)
C23	0.0163 (7)	0.0215 (7)	0.0172 (7)	0.0087 (6)	−0.0010 (5)	−0.0026 (5)
C13	0.0173 (7)	0.0201 (7)	0.0164 (6)	0.0089 (6)	−0.0009 (5)	−0.0011 (5)
C32	0.0175 (7)	0.0214 (7)	0.0160 (6)	0.0091 (6)	−0.0005 (5)	0.0008 (5)
C24	0.0202 (7)	0.0222 (7)	0.0148 (6)	0.0119 (6)	−0.0010 (5)	−0.0020 (5)
C14	0.0212 (7)	0.0203 (7)	0.0139 (6)	0.0126 (6)	−0.0002 (5)	0.0006 (5)
C33	0.0195 (7)	0.0192 (7)	0.0160 (6)	0.0099 (6)	−0.0006 (5)	0.0000 (5)
C34	0.0176 (7)	0.0176 (7)	0.0156 (6)	0.0064 (6)	−0.0012 (5)	−0.0004 (5)
C25	0.0203 (7)	0.0186 (7)	0.0157 (6)	0.0091 (6)	−0.0015 (5)	−0.0032 (5)
C15	0.0200 (7)	0.0178 (7)	0.0144 (6)	0.0091 (6)	−0.0002 (5)	−0.0009 (5)
C35	0.0161 (6)	0.0205 (7)	0.0163 (6)	0.0077 (6)	0.0002 (5)	0.0002 (5)
C35A	0.0195 (7)	0.0209 (7)	0.0176 (7)	0.0115 (6)	−0.0039 (5)	−0.0004 (5)
C25A	0.0146 (6)	0.0202 (7)	0.0158 (6)	0.0070 (5)	0.0019 (5)	0.0002 (5)
C15A	0.0151 (6)	0.0190 (7)	0.0141 (6)	0.0072 (5)	0.0023 (5)	0.0011 (5)
C16	0.0172 (7)	0.0200 (7)	0.0159 (6)	0.0076 (6)	0.0011 (5)	−0.0011 (5)
C17	0.0159 (7)	0.0275 (7)	0.0140 (6)	0.0079 (6)	−0.0019 (5)	0.0016 (6)
C36	0.0208 (7)	0.0249 (7)	0.0206 (7)	0.0126 (6)	−0.0010 (6)	−0.0006 (6)
C26	0.0176 (7)	0.0217 (7)	0.0177 (7)	0.0065 (6)	−0.0001 (5)	−0.0019 (5)
C18	0.0196 (7)	0.0240 (7)	0.0235 (7)	0.0122 (6)	−0.0009 (6)	0.0056 (6)
C37	0.0292 (8)	0.0308 (8)	0.0211 (7)	0.0190 (7)	−0.0041 (6)	−0.0081 (6)
C27	0.0180 (7)	0.0292 (8)	0.0163 (7)	0.0091 (6)	−0.0035 (5)	0.0004 (6)
C19	0.0200 (7)	0.0194 (7)	0.0191 (7)	0.0089 (6)	0.0002 (5)	0.0013 (5)
C38	0.0246 (8)	0.0242 (8)	0.0305 (8)	0.0112 (6)	−0.0068 (6)	−0.0090 (6)
C28	0.0190 (7)	0.0247 (7)	0.0226 (7)	0.0114 (6)	−0.0008 (6)	0.0033 (6)
C19A	0.0148 (6)	0.0182 (7)	0.0150 (6)	0.0064 (5)	0.0018 (5)	0.0014 (5)
C39	0.0205 (7)	0.0229 (7)	0.0242 (7)	0.0088 (6)	−0.0035 (6)	−0.0025 (6)
C29	0.0184 (7)	0.0197 (7)	0.0199 (7)	0.0083 (6)	0.0010 (5)	−0.0003 (5)
C110	0.0214 (7)	0.0192 (7)	0.0148 (6)	0.0105 (6)	−0.0005 (5)	0.0004 (5)
C29A	0.0136 (6)	0.0191 (7)	0.0142 (6)	0.0054 (5)	0.0016 (5)	0.0010 (5)
C111	0.0221 (7)	0.0214 (7)	0.0180 (7)	0.0103 (6)	0.0011 (5)	−0.0006 (5)
C39A	0.0192 (7)	0.0219 (7)	0.0169 (7)	0.0114 (6)	−0.0030 (5)	−0.0008 (5)
C210	0.0212 (7)	0.0204 (7)	0.0156 (6)	0.0110 (6)	−0.0032 (5)	−0.0024 (5)
C112	0.0204 (7)	0.0221 (7)	0.0231 (7)	0.0059 (6)	−0.0020 (6)	−0.0026 (6)
C211	0.0219 (7)	0.0221 (7)	0.0176 (7)	0.0120 (6)	−0.0007 (5)	−0.0007 (5)
C113	0.0238 (7)	0.0252 (8)	0.0212 (7)	0.0066 (6)	−0.0022 (6)	−0.0027 (6)
C212	0.0188 (7)	0.0223 (7)	0.0242 (7)	0.0084 (6)	−0.0034 (6)	−0.0036 (6)
C114	0.0281 (8)	0.0312 (8)	0.0231 (8)	0.0110 (7)	−0.0040 (6)	−0.0048 (6)
C310	0.0286 (8)	0.0210 (7)	0.0206 (7)	0.0098 (6)	0.0049 (6)	0.0006 (6)
C311	0.0266 (9)	0.0180 (10)	0.0206 (9)	0.0109 (8)	0.0057 (7)	0.0001 (8)
C312	0.0243 (9)	0.0282 (9)	0.0239 (9)	0.0158 (7)	0.0041 (7)	0.0039 (7)
C313	0.0289 (9)	0.0337 (10)	0.0203 (8)	0.0186 (8)	0.0023 (7)	0.0009 (7)
C314	0.0274 (14)	0.0324 (11)	0.0222 (10)	0.0137 (11)	0.0009 (9)	−0.0014 (8)
C315	0.0286 (8)	0.0210 (7)	0.0206 (7)	0.0098 (6)	0.0049 (6)	0.0006 (6)
C316	0.034 (2)	0.022 (2)	0.025 (2)	0.0130 (17)	0.0087 (19)	−0.004 (2)
C317	0.028 (2)	0.026 (2)	0.021 (2)	0.0145 (19)	0.0042 (19)	0.000 (2)
C318	0.030 (2)	0.033 (2)	0.022 (2)	0.009 (2)	0.005 (2)	−0.003 (2)
C319	0.032 (5)	0.036 (5)	0.019 (4)	0.010 (5)	0.009 (4)	−0.001 (4)
C214	0.0352 (9)	0.0323 (9)	0.0230 (8)	0.0157 (7)	0.0017 (7)	−0.0036 (6)
C213	0.0287 (8)	0.0226 (7)	0.0222 (7)	0.0120 (6)	−0.0084 (6)	−0.0048 (6)

Geometric parameters (Å, º) top

N11—C19A	1.4347 (16)	C32—C33	1.5283 (18)
N11—C12	1.4938 (17)	C24—C25	1.5342 (18)
F11—C17	1.3646 (15)	C14—C15	1.5370 (18)
C411—C410	1.317 (2)	C33—C34	1.5201 (18)
C411—C412	1.511 (9)	C34—C35	1.5378 (18)
C412—C413	1.497 (10)	C25—C25A	1.5084 (18)
C413—C414	1.527 (8)	C15—C15A	1.5041 (18)
C416—C417	1.518 (6)	C35—C35A	1.5085 (18)
C417—C418	1.523 (6)	C35A—C36	1.3989 (19)
C420—C421	1.515 (8)	C35A—C39A	1.4016 (19)
C421—C422	1.540 (7)	C25A—C26	1.3980 (18)
C410—C42	1.5042 (19)	C25A—C29A	1.4045 (19)
C49A—C49	1.3956 (19)	C15A—C16	1.3989 (18)
C49A—C45A	1.4040 (19)	C15A—C19A	1.4044 (18)
C49A—N41	1.4313 (17)	C16—C17	1.3757 (19)
C49—C48	1.388 (2)	C17—C18	1.375 (2)
C48—C47	1.374 (2)	C36—C37	1.376 (2)
C47—F41	1.3660 (16)	C26—C27	1.376 (2)
C47—C46	1.375 (2)	C18—C19	1.3881 (19)
C46—C45A	1.3964 (19)	C37—C38	1.373 (2)
C45A—C45	1.5091 (18)	C27—C28	1.373 (2)
C45—C44	1.5368 (18)	C19—C19A	1.3934 (19)
C44—O41	1.4320 (16)	C38—C39	1.387 (2)
C44—C43	1.5176 (18)	C28—C29	1.3873 (19)
C43—C42	1.5276 (19)	C39—C39A	1.3973 (19)
C42—N41	1.4940 (18)	C29—C29A	1.3972 (19)
O11—C14	1.4340 (15)	C110—C111	1.3219 (19)
N21—C29A	1.4347 (16)	C111—C112	1.5015 (19)
N21—C22	1.4970 (17)	C210—C211	1.3227 (19)
F21—C27	1.3666 (15)	C112—C113	1.518 (2)
O21—C24	1.4342 (16)	C211—C212	1.4999 (19)
C22—C210	1.5016 (18)	C113—C114	1.5222 (19)
C22—C23	1.5240 (18)	C212—C213	1.526 (2)
C12—C110	1.5063 (18)	C310—C311	1.343 (2)
C12—C13	1.5305 (18)	C311—C312	1.514 (2)
N31—C39A	1.4323 (17)	C312—C313	1.511 (2)
N31—C32	1.4917 (17)	C313—C314	1.523 (2)
F31—C37	1.3674 (16)	C316—C317	1.509 (4)
O31—C34	1.4350 (16)	C317—C318	1.510 (4)
C23—C24	1.5213 (18)	C318—C319	1.512 (4)
C13—C14	1.5184 (18)	C214—C213	1.521 (2)
C32—C310	1.5024 (19)

C19A—N11—C12	116.72 (10)	C15A—C15—C14	113.62 (11)
C410—C411—C412	122.9 (5)	C35A—C35—C34	114.54 (11)
C413—C412—C411	119.1 (8)	C36—C35A—C39A	118.74 (12)
C412—C413—C414	109.6 (7)	C36—C35A—C35	119.63 (12)
C416—C417—C418	112.3 (4)	C39A—C35A—C35	121.62 (12)
C420—C421—C422	112.7 (6)	C26—C25A—C29A	118.75 (12)
C411—C410—C42	123.74 (16)	C26—C25A—C25	119.16 (12)
C49—C49A—C45A	119.63 (13)	C29A—C25A—C25	122.08 (12)
C49—C49A—N41	119.29 (12)	C16—C15A—C19A	118.67 (12)
C45A—C49A—N41	121.02 (12)	C16—C15A—C15	119.72 (12)
C48—C49—C49A	121.30 (13)	C19A—C15A—C15	121.60 (11)
C47—C48—C49	117.91 (13)	C17—C16—C15A	119.82 (12)
F41—C47—C48	118.94 (13)	F11—C17—C18	119.20 (12)
F41—C47—C46	118.51 (13)	F11—C17—C16	118.28 (12)
C48—C47—C46	122.54 (13)	C18—C17—C16	122.52 (12)
C47—C46—C45A	119.92 (13)	C37—C36—C35A	119.64 (13)
C46—C45A—C49A	118.69 (12)	C27—C26—C25A	119.71 (13)
C46—C45A—C45	119.41 (12)	C17—C18—C19	117.96 (13)
C49A—C45A—C45	121.90 (12)	F31—C37—C38	119.07 (13)
C45A—C45—C44	114.61 (11)	F31—C37—C36	118.20 (13)
O41—C44—C43	106.43 (10)	C38—C37—C36	122.72 (13)
O41—C44—C45	109.82 (10)	F21—C27—C28	119.07 (12)
C43—C44—C45	112.84 (11)	F21—C27—C26	118.20 (12)
C44—C43—C42	116.23 (11)	C28—C27—C26	122.72 (13)
N41—C42—C410	108.08 (12)	C18—C19—C19A	121.31 (13)
N41—C42—C43	112.55 (11)	C37—C38—C39	118.00 (13)
C410—C42—C43	108.60 (11)	C27—C28—C29	117.90 (13)
C29A—N21—C22	115.16 (10)	C19—C19A—C15A	119.72 (12)
N21—C22—C210	109.25 (10)	C19—C19A—N11	119.51 (12)
N21—C22—C23	112.08 (11)	C15A—C19A—N11	120.70 (12)
C210—C22—C23	108.45 (11)	C38—C39—C39A	121.09 (14)
N11—C12—C110	107.90 (10)	C28—C29—C29A	121.29 (13)
N11—C12—C13	112.54 (11)	C111—C110—C12	124.10 (12)
C110—C12—C13	108.31 (10)	C29—C29A—C25A	119.61 (12)
C39A—N31—C32	116.73 (10)	C29—C29A—N21	119.36 (12)
C49A—N41—C42	116.76 (10)	C25A—C29A—N21	121.00 (12)
C24—C23—C22	116.08 (11)	C110—C111—C112	126.52 (13)
C14—C13—C12	117.19 (11)	C39—C39A—C35A	119.80 (13)
N31—C32—C310	107.59 (11)	C39—C39A—N31	119.25 (12)
N31—C32—C33	112.30 (11)	C35A—C39A—N31	120.89 (12)
C310—C32—C33	109.59 (11)	C211—C210—C22	123.08 (12)
O21—C24—C23	106.52 (10)	C111—C112—C113	115.91 (12)
O21—C24—C25	109.80 (11)	C210—C211—C212	127.95 (13)
C23—C24—C25	113.00 (11)	C112—C113—C114	111.64 (12)
O11—C14—C13	105.99 (10)	C211—C212—C213	116.65 (12)
O11—C14—C15	110.20 (10)	C311—C310—C32	121.91 (14)
C13—C14—C15	112.89 (11)	C310—C311—C312	125.68 (17)
C34—C33—C32	116.27 (11)	C313—C312—C311	116.45 (15)
O31—C34—C33	106.46 (10)	C312—C313—C314	111.25 (16)
O31—C34—C35	109.70 (10)	C316—C317—C318	107.7 (7)
C33—C34—C35	112.93 (11)	C317—C318—C319	110.1 (9)
C25A—C25—C24	114.85 (11)	C214—C213—C212	112.71 (12)

C410—C411—C412—C413	16.5 (14)	C15—C15A—C16—C17	180.00 (12)
C411—C412—C413—C414	173.5 (8)	C15A—C16—C17—F11	−179.65 (11)
C412—C411—C410—C42	−177.6 (7)	C15A—C16—C17—C18	0.4 (2)
C45A—C49A—C49—C48	0.1 (2)	C39A—C35A—C36—C37	0.2 (2)
N41—C49A—C49—C48	177.53 (12)	C35—C35A—C36—C37	−178.61 (13)
C49A—C49—C48—C47	0.8 (2)	C29A—C25A—C26—C27	0.76 (19)
C49—C48—C47—F41	179.33 (12)	C25—C25A—C26—C27	−178.24 (12)
C49—C48—C47—C46	−0.9 (2)	F11—C17—C18—C19	179.85 (12)
F41—C47—C46—C45A	179.89 (12)	C16—C17—C18—C19	−0.2 (2)
C48—C47—C46—C45A	0.2 (2)	C35A—C36—C37—F31	179.48 (12)
C47—C46—C45A—C49A	0.78 (19)	C35A—C36—C37—C38	0.0 (2)
C47—C46—C45A—C45	−178.47 (12)	C25A—C26—C27—F21	179.64 (12)
C49—C49A—C45A—C46	−0.91 (19)	C25A—C26—C27—C28	0.1 (2)
N41—C49A—C45A—C46	−178.27 (12)	C17—C18—C19—C19A	−0.1 (2)
C49—C49A—C45A—C45	178.32 (12)	F31—C37—C38—C39	−179.87 (12)
N41—C49A—C45A—C45	0.96 (19)	C36—C37—C38—C39	−0.4 (2)
C46—C45A—C45—C44	−119.35 (13)	F21—C27—C28—C29	179.62 (12)
C49A—C45A—C45—C44	61.43 (16)	C26—C27—C28—C29	−0.9 (2)
C45A—C45—C44—O41	164.37 (11)	C18—C19—C19A—C15A	0.2 (2)
C45A—C45—C44—C43	−77.07 (14)	C18—C19—C19A—N11	−176.67 (12)
O41—C44—C43—C42	−175.04 (11)	C16—C15A—C19A—C19	0.00 (19)
C45—C44—C43—C42	64.44 (15)	C15—C15A—C19A—C19	179.73 (12)
C411—C410—C42—N41	129.58 (16)	C16—C15A—C19A—N11	176.83 (11)
C411—C410—C42—C43	−108.04 (17)	C15—C15A—C19A—N11	−3.44 (19)
C44—C43—C42—N41	−64.28 (15)	C12—N11—C19A—C19	−114.64 (13)
C44—C43—C42—C410	176.10 (12)	C12—N11—C19A—C15A	68.53 (16)
C29A—N21—C22—C210	−156.69 (11)	C37—C38—C39—C39A	0.6 (2)
C29A—N21—C22—C23	83.09 (13)	C27—C28—C29—C29A	0.7 (2)
C19A—N11—C12—C110	161.36 (11)	N11—C12—C110—C111	−132.05 (14)
C19A—N11—C12—C13	−79.20 (14)	C13—C12—C110—C111	105.86 (15)
C49—C49A—N41—C42	117.04 (14)	C28—C29—C29A—C25A	0.1 (2)
C45A—C49A—N41—C42	−65.59 (16)	C28—C29—C29A—N21	178.50 (12)
C410—C42—N41—C49A	−159.36 (12)	C26—C25A—C29A—C29	−0.89 (19)
C43—C42—N41—C49A	80.71 (14)	C25—C25A—C29A—C29	178.08 (12)
N21—C22—C23—C24	−66.36 (14)	C26—C25A—C29A—N21	−179.22 (12)
C210—C22—C23—C24	172.95 (11)	C25—C25A—C29A—N21	−0.25 (19)
N11—C12—C13—C14	60.97 (15)	C22—N21—C29A—C29	116.14 (13)
C110—C12—C13—C14	−179.82 (11)	C22—N21—C29A—C25A	−65.52 (16)
C39A—N31—C32—C310	−158.27 (11)	C12—C110—C111—C112	−176.79 (13)
C39A—N31—C32—C33	81.05 (14)	C38—C39—C39A—C35A	−0.4 (2)
C22—C23—C24—O21	−175.67 (11)	C38—C39—C39A—N31	176.81 (13)
C22—C23—C24—C25	63.68 (15)	C36—C35A—C39A—C39	0.0 (2)
C12—C13—C14—O11	175.57 (11)	C35—C35A—C39A—C39	178.78 (12)
C12—C13—C14—C15	−63.70 (15)	C36—C35A—C39A—N31	−177.17 (12)
N31—C32—C33—C34	−63.64 (15)	C35—C35A—C39A—N31	1.64 (19)
C310—C32—C33—C34	176.84 (12)	C32—N31—C39A—C39	116.01 (14)
C32—C33—C34—O31	−175.46 (11)	C32—N31—C39A—C35A	−66.84 (16)
C32—C33—C34—C35	64.10 (15)	N21—C22—C210—C211	122.85 (14)
O21—C24—C25—C25A	165.75 (10)	C23—C22—C210—C211	−114.73 (14)
C23—C24—C25—C25A	−75.49 (14)	C110—C111—C112—C113	−5.0 (2)
O11—C14—C15—C15A	−163.06 (10)	C22—C210—C211—C212	173.60 (13)
C13—C14—C15—C15A	78.65 (14)	C111—C112—C113—C114	−179.24 (13)
O31—C34—C35—C35A	164.07 (11)	C210—C211—C212—C213	9.3 (2)
C33—C34—C35—C35A	−77.36 (14)	N31—C32—C310—C311	128.42 (16)
C34—C35—C35A—C36	−119.81 (13)	C33—C32—C310—C311	−109.21 (17)
C34—C35—C35A—C39A	61.39 (17)	C32—C310—C311—C312	−178.55 (15)
C24—C25—C25A—C26	−118.94 (13)	C310—C311—C312—C313	15.3 (3)
C24—C25—C25A—C29A	62.09 (16)	C311—C312—C313—C314	176.05 (19)
C14—C15—C15A—C16	118.18 (13)	C316—C317—C318—C319	174.7 (10)
C14—C15—C15A—C19A	−61.55 (16)	C211—C212—C213—C214	72.12 (16)
C19A—C15A—C16—C17	−0.27 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1N···O31ⁱ	0.906 (16)	2.287 (16)	3.1897 (15)	173.9 (13)
N21—H2N···O11ⁱⁱ	0.895 (16)	2.370 (17)	3.2455 (15)	165.8 (13)
N31—H3N···O21ⁱⁱⁱ	0.901 (17)	2.326 (17)	3.2208 (15)	172.2 (14)
N41—H4N···O41^iv	0.893 (16)	2.310 (16)	3.1952 (15)	170.9 (14)
O11—H1O···N11^v	0.869 (19)	2.00 (2)	2.8553 (15)	166.1 (17)
O21—H2O···N41	0.89 (2)	1.98 (2)	2.8542 (15)	168.6 (18)
O31—H3O···N21	0.864 (19)	2.008 (19)	2.8619 (15)	169.5 (17)
O41—H4O···N31ⁱ	0.88 (2)	2.00 (2)	2.8570 (15)	167.3 (17)

Symmetry codes: (i) x, y, z+1; (ii) −y+2/3, x−y+1/3, z−2/3; (iii) x−y+2/3, x+1/3, −z+1/3; (iv) y−1/3, −x+y+1/3, −z+4/3; (v) −x+y+1/3, −x+2/3, z−1/3.

Experimental details

	(Compound_1)	(Compound_2)	(Compound_3)
Crystal data
Chemical formula	C₂₂H₂₁NO	C₂₂H₂₁NO	C₂₂H₂₁NO
M_r	315.40	315.40	315.40
Crystal system, space group	Monoclinic, P2₁/c	Orthorhombic, P2₁2₁2₁	Monoclinic, P2₁
Temperature (K)	100	298	100
a, b, c (Å)	24.8049 (10), 10.7126 (5), 12.1932 (4)	7.5541 (3), 14.7914 (5), 15.4049 (5)	7.2201 (2), 7.8128 (3), 14.7409 (5)
α, β, γ (°)	90, 95.929 (1), 90	90, 90, 90	90, 93.690 (2), 90
V (Å³)	3222.7 (2)	1721.28 (11)	829.80 (5)
Z	8	4	2
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.08	0.07	0.08
Crystal size (mm)	0.45 × 0.35 × 0.20	0.51 × 0.32 × 0.25	0.30 × 0.30 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII	Bruker Kappa APEXII	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2006)	Multi-scan (SADABS; Bruker, 2006)	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.640, 0.746	0.86, 0.98	0.92, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	48596, 7121, 6012	69991, 5630, 4013	27947, 4874, 4638
R_int	0.040	0.041	0.023
(sin θ/λ)_max (Å⁻¹)	0.649	0.734	0.709

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 1.04	0.043, 0.109, 1.03	0.033, 0.092, 1.04
No. of reflections	7121	5630	4874
No. of parameters	437	220	219
No. of restraints	0	0	1
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0523P)² + 2.1093P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0474P)² + 0.1943P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.0566P)² + 0.1148P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26	0.17, −0.16	0.30, −0.19
Absolute structure	?	Refined as an inversion twin	Flack x determined using 2066 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter	?	0 (2)	−0.1 (3)

	(Compound_4)	(Compound_5a)	(Compound_5b)
Crystal data
Chemical formula	C₁₈H₁₈FNO	C₁₅H₂₀FNO	C₁₅H₂₀FNO
M_r	283.33	249.32	249.32
Crystal system, space group	Orthorhombic, Pbca	Trigonal, R3:H	Trigonal, R3:H
Temperature (K)	100	298	100
a, b, c (Å)	7.5932 (3), 7.5859 (4), 51.010 (3)	25.119 (2), 25.119 (2), 11.2812 (12)	49.395 (2), 49.395 (2), 11.1802 (5)
α, β, γ (°)	90, 90, 90	90, 90, 120	90, 90, 120
V (Å³)	2938.2 (2)	6164.2 (12)	23623 (2)
Z	8	18	72
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.09	0.08	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20	0.30 × 0.25 × 0.20	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII	Bruker Kappa APEXII	Bruker Kappa APEXII
Absorption correction	Multi-scan (SADABS; Bruker, 2006)	Multi-scan (SADABS; Bruker, 2006)	Multi-scan (SADABS; Bruker, 2006)
T_min, T_max	0.90, 0.98	0.68, 0.74	0.89, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	40696, 3764, 3407	34372, 2814, 2024	124259, 12035, 8771
R_int	0.027	0.036	0.043
(sin θ/λ)_max (Å⁻¹)	0.709	0.625	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.108, 1.09	0.066, 0.229, 1.07	0.046, 0.122, 1.02
No. of reflections	3764	2814	12035
No. of parameters	198	212	786
No. of restraints	0	159	459
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0371P)² + 2.0455P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.1155P)² + 11.0098P] where P = (F_o² + 2F_c²)/3	w = 1/[σ²(F_o²) + (0.048P)² + 28.8932P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23	0.55, −0.41	0.44, −0.28
Absolute structure	?	?	?
Absolute structure parameter	?	?	?

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SIR92 (Altomare et al., 1994), SUPERFLIP (Palatinus & Chapuis, 2007), SHELXL2014 (Sheldrick, 2015), SHELXL2014 (Sheldrick, 2008a, 2015b), Mercury (Macrae et al., 2008).

Selected ring-puckering parameters (Å, °) top

For compounds (1)–(3), ring-puckering parameters in the five-membered rings refer to the atom sequence O1–N1–C2–C3–C4 and those in the six-membered rings refer to the atom sequence O1–N1–C9A–C5A–C5–C4. For compounds (4) and (5), ring-puckering parameters in the seven-membered rings refer to the atom sequence N1–C2–C3–C4–C5–C5A–C9A.

Five-membered rings
Molecule	Q₂	φ₂
(1A)	0.4489 (14)	191.38 (19)
(1B)	0.4678 (14)	202.91 (19)
(2)	0.443 (2)	197.0 (3)
(3)	0.4431 (14)	195.7 (2)
Idealized half-chair		234°
Idealized envelope		180°

Six-membered rings
Molecule	Q	θ	φ
(1A)	0.6289 (13)	55.02 (13)	348.05 (17)
(1B)	0.6332 (14)	53.46 (13)	342.82 (17)
(2)	0.629 (2)	53.01 (18)	342.4 (2)
(3)	0.6260 (14)	53.20 (13)	343.83 (17)
Idealized half-chair		50.8°	330°
Idealized envelope		54.7°	360°

Seven-membered rings
Molecule	Q₂	φ₂	φ₃
(4)	0.3446 (12)	164.5 (2)	230.19 (11)
(5RT)	0.385 (3)	154.7 (4)	231.6 (2)
(5LT), Molecule 1	0.4038 (15)	148.8 (2)	231.63 (13)
(5LT), Molecule 2	0.3760 (15)	158.2 (2)	231.28 (13)
(5LT), Molecule 3	0.3708 (15)	153.3 (2)	231.88 (14)
(5LT), Molecule 4	0.3790 (15)	152.7 (2)	231.65 (13)

Hydrogen-bond geometry (Å, º) for (Compound_1) top

D—H···A	D—H	H···A	D···A	D—H···A
C2A—H2A···O1Aⁱ	1.00	2.61	3.4061 (17)	137
C5A—H5AA···Cg_1A2ⁱⁱ	1.00	2.60	3.5600 (16)	163
C4B—H4B···O1Bⁱⁱⁱ	1.00	2.43	3.1601 (18)	129

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

Hydrogen-bond geometry (Å, º) for (Compound_2) top

D—H···A	D—H	H···A	D···A	D—H···A
C82—H82···O1ⁱ	0.959	2.66	3.587 (3)	164

Symmetry code: (i) −x+2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) for (Compound_3) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.95	2.59	3.3880 (19)	141.9
C27—H27···Cg₃₁ⁱⁱ	0.95	2.86	3.6294 (16)	139
C28—H28···Cg₃₂ⁱⁱ	0.95	2.90	3.6116 (16)	133

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

Hydrogen-bond geometry (Å, º) for (Compound_4) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.904 (17)	2.450 (16)	3.2709 (14)	151 (13)
O1—H1O···N1ⁱⁱ	0.88 (2)	2.14 (2)	3.0187 (14)	172.9 (16)
C5—H5A···N1ⁱⁱ	0.99	2.67	3.3657 (16)	127.6
C6—H6···F1ⁱⁱⁱ	0.95	2.47	3.4236 (16)	176.8
C5—H5A···O1^iv	0.99	2.53	3.4027 (15)	147.5

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

Hydrogen-bond geometry (Å, º) for (Compound_5a) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O7ⁱ	0.88 (3)	2.49 (3)	3.356 (3)	171 (3)
O7—H7O···N1ⁱⁱ	0.88	2.02	2.889 (3)	168.8
C9—H9···O7ⁱ	0.93	2.63	3.451 (4)	147.3

Symmetry codes: (i) x−y+2/3, x+1/3, −z+4/3; (ii) −y+2/3, x−y+1/3, z+1/3.

Hydrogen-bond geometry (Å, º) for (Compound_5b) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H1N···O31ⁱ	0.906 (16)	2.287 (16)	3.1897 (15)	173.9 (13)
N21—H2N···O11ⁱⁱ	0.895 (16)	2.370 (17)	3.2455 (15)	165.8 (13)
N31—H3N···O21ⁱⁱⁱ	0.901 (17)	2.326 (17)	3.2208 (15)	172.2 (14)
N41—H4N···O41^iv	0.893 (16)	2.310 (16)	3.1952 (15)	170.9 (14)
O11—H1O···N11^v	0.869 (19)	2.00 (2)	2.8553 (15)	166.1 (17)
O21—H2O···N41	0.89 (2)	1.98 (2)	2.8542 (15)	168.6 (18)
O31—H3O···N21	0.864 (19)	2.008 (19)	2.8619 (15)	169.5 (17)
O41—H4O···N31ⁱ	0.88 (2)	2.00 (2)	2.8570 (15)	167.3 (17)

Symmetry codes: (i) x, y, z+1; (ii) −y+2/3, x−y+1/3, z−2/3; (iii) x−y+2/3, x+1/3, −z+1/3; (iv) y−1/3, −x+y+1/3, −z+4/3; (v) −x+y+1/3, −x+2/3, z−1/3.

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Crystal structures of five new substituted tetra­hydro-1-benzazepines with potential anti­parasitic activity

Supporting information

Crystal structures of five new substituted tetrahydro-1-benzazepines with potential antiparasitic activity