Crystal structure and Hirshfeld surface analysis of 1,3,3-trimethyl-2,6-di­phenyl­piperidin-4-yl 2-phenyl­prop-2-enoate

Ananthabharathi, A.; Janarthanan, S.; Gopalakrishnan, M.; Pazhamalai, S.; Selvanayagam, S.

doi:10.1107/S2056989025008709

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ISSN: 2056-9890

Volume 81| Part 11| November 2025| Pages 1004-1007

https://doi.org/10.1107/S2056989025008709

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Crystal structure and Hirshfeld surface analysis of 1,3,3-trimethyl-2,6-diphenylpiperidin-4-yl 2-phenylprop-2-enoate

Aranganathan Ananthabharathi,^a Sekar Janarthanan,^a Mannathusamy Gopalakrishnan,^a Srinivasan Pazhamalai ^a ^* and Sivashanmugam Selvanayagam ^b ‡

^aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and ^bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 10 September 2025; accepted 3 October 2025; online 9 October 2025)

The title compound, C₂₉H₃₁NO₂, is a multi-substituted piperidine derivative in which the piperidine ring adopts a chair conformation. Intermolecular C—H⋯O hydrogen bonds as well as C—H⋯π interactions are observed in the crystal, leading to the formation of inversion dimers and chains, respectively. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis, revealing that H⋯H interactions contribute the most (70.5%) to the crystal packing.

Keywords: piperidine derivative; intermolecular hydrogen bonds; crystal structure.

CCDC reference: 2493059

1. Chemical context

Compounds with piperidine-based scaffolds represent an important class of nitrogen heterocycles, occurring widely in natural alkaloids and serving as versatile building blocks in medicinal chemistry due to their wide-ranging pharmacological importance. Examples are arecoline and pethidine. Moreover, piperidine derivatives show therapeutic properties as anti-cancer, antimicrobial, analgesic, anti-inflammatory, or antipsychotic agents (Abdelshaheed et al., 2021 ). Structural modifications on the piperidine framework often modulate biological activity, lipophilicity, and supramolecular interactions, making them valuable targets for both medicinal and crystallographic studies (Mitra et al., 2022 ; Grover et al., 2023 ).

In the context of piperidine frameworks given above, we synthesized the title compound, (I), C₂₉H₃₁NO₂, and report here its molecular and crystal structures, as well as the results of a Hirshfeld surface analysis.

2. Structural commentary

The molecular structure of (I) is shown in Fig. 1. The C13=O2 [1.198 (2) Å] and C14=C15 [1.319 (2) Å] bond lengths confirm the double-bond character. The piperidine ring (N1/C1–C5) adopts a chair conformation with puckering parameters (Cremer & Pople, 1975 ) of q₂ = 0.101 (2) Å, q₃ = −0.553 (2) Å, Q_T = 0.562 (2) Å, θ = 169.7 (2)° and φ = 24.4 (9)°. Atoms C1 and C4 deviate by 0.574 (2) and −0.726 (1) Å, respectively, from the least-squares plane through the remaining four atoms (N1/C2/C3/C5) of the ring. The mean plane calculation of the prop-2-enoic acid moiety (O1/C13/O2/C14/C15) reveals that atoms C15 and C14 deviate by −0.050 (2) and 0.038 (2) Å, respectively, from the plane. This moiety makes a dihedral angle of 54.1 (1)° with respect to the attached phenyl ring (C16–C21). The two other phenyl rings (C7–C12 and C24–C29) subtend a dihedral angle of 26.6 (1)°.

Figure 1
The molecular structure of compound (I)

, showing the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. Intramolecular short contacts are shown as dashed lines.

3. Supramolecular features

In the crystal, molecules associate pairwise via C18—H18⋯O2ⁱ hydrogen bonds (Table 1) into inversion dimers with an R₂²(14) graph-set motif (Etter et al., 1990 ; Bernstein et al., 1995 ), as shown in Fig. 2. In addition, molecules are linked into a C(5) chain motif by C—H⋯π interactions, C15—H15A⋯Cg, where Cg is the centroid of the C16–C21 benzene ring of the symmetry-related molecules at x, y + 1, z (Table 1). These C(5) chains run in a parallel manner along the [010] direction (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C16–C21 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.55	3.473 (3)	170
C15—H15A⋯Cgⁱⁱ	0.93	2.94	3.613 (2)	130
Symmetry codes: (i) ; (ii) .

Figure 2
The formation of an inversion dimer through C—H⋯O hydrogen bonds in the crystal structure of (I)

. [Symmetry code: (a) −x, −y − 1, −z.]

Figure 3
The crystal packing of (I)

. Intermolecular C—H⋯π interactions are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

4. Hirshfeld surface analysis

In order to further characterize and quantify the intermolecular interactions in the title compound, a Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ) was carried out using CrystalExplorer (Spackman et al., 2021 ). The HS mapped over d_norm is illustrated in Fig. 4 where the deep-red spots at O2 and H18 are indicative of the intermolecular C—H⋯O hydrogen bonds discussed in the previous section.

Figure 4
A view of the Hirshfeld surface mapped over d_norm for compound (I)

The associated two-dimensional fingerprint plots (McKinnon et al., 2007 ) provide quantitative information about the non-covalent interactions in the crystal packing in terms of the percentage contribution of the interatomic contacts (Spackman & McKinnon, 2002 ). As shown in Fig. 5, the overall two-dimensional fingerprint plot for compound (I) is delineated in H⋯H, H⋯C/C⋯H, H⋯O/O⋯H and C⋯C contacts, revealing that H⋯H and H⋯C/C⋯H are the main contributors to the crystal packing.

Figure 5
Two-dimensional fingerprint plots for compound (I)

, showing all interactions, and delineated into H⋯H, H⋯C/C⋯H, H⋯O/O⋯H and C⋯C interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

5. Synthesis and crystallization

>A solution of 1,3,3-trimethyl-2,6-diphenylpiperidin-4-ol (0.5 g), tropic acid (0.29 g), N,N′-dicyclohexylcarbodiimide (0.74 g) and N,N-dimethylaminopyridine 0.25 g) in dry dichloromethane (30 ml) was refluxed at 313 K for 6–8 h. After filtration, the organic layer was washed with aqueous NaHCO₃ (10%_wt) and brine. The combined organic layer was then concentrated under reduced pressure. The crude ester was purified by column chromatography (silica gel 100–200 mesh, petroleum ether/ethyl acetate v:v 9:1) and recrystallized from acetonitrile solution (99%), affording colourless crystals of the title compound [see Jordan et al., 2021 ) for the synthesis procedure for esterification by using DCC and DMAP catalysts].

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å, with U_iso(H) = 1.5U_eq(C-methyl) and 1.2U_eq for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₉H₃₁NO₂
M_r	425.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	13.2165 (8), 5.8983 (4), 31.503 (2)
β (°)	99.174 (2)
V (Å³)	2424.4 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.36 × 0.22 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.975, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	43823, 6019, 4053
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.168, 1.03
No. of reflections	6019
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20
Computer programs: APEX3 and SAINT (Bruker, 2017 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2493059

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989025008709/wm5771sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025008709/wm5771Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025008709/wm5771Isup3.cml

checkCIF report

Computing details top

1,3,3-Trimethyl-2,6-diphenylpiperidin-4-yl 2-phenylprop-2-enoate top

Crystal data top

C₂₉H₃₁NO₂	F(000) = 912
M_r = 425.55	D_x = 1.166 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.2165 (8) Å	Cell parameters from 9887 reflections
b = 5.8983 (4) Å	θ = 2.8–27.9°
c = 31.503 (2) Å	µ = 0.07 mm⁻¹
β = 99.174 (2)°	T = 300 K
V = 2424.4 (3) Å³	Block, colourless
Z = 4	0.36 × 0.22 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	4053 reflections with I > 2σ(I)
Radiation source: i-mu-s microfocus source	R_int = 0.041
ω and φ scans	θ_max = 28.3°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −17→17
T_min = 0.975, T_max = 0.988	k = −7→7
43823 measured reflections	l = −41→42
6019 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.052	w = 1/[σ²(F_o²) + (0.0655P)² + 0.7185P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.168	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.18 e Å⁻³
6019 reflections	Δρ_min = −0.20 e Å⁻³
290 parameters	Extinction correction: SHELXL (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0181 (18)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
O1	0.03926 (8)	0.06917 (18)	0.11420 (4)	0.0611 (3)
O2	0.01154 (12)	−0.2824 (2)	0.08983 (5)	0.0893 (5)
N1	0.32017 (9)	0.0625 (2)	0.20033 (4)	0.0513 (3)
C1	0.32010 (12)	−0.0081 (3)	0.15561 (5)	0.0552 (4)
H1	0.324364	−0.173859	0.154789	0.066*
C2	0.22312 (12)	0.0663 (3)	0.12589 (5)	0.0588 (4)
H2A	0.223440	0.229827	0.122584	0.071*
H2B	0.221726	−0.001316	0.097742	0.071*
C3	0.12920 (11)	−0.0044 (3)	0.14390 (5)	0.0522 (4)
H3	0.128246	−0.169932	0.146411	0.063*
C4	0.12649 (11)	0.1003 (2)	0.18778 (5)	0.0496 (4)
C5	0.22462 (10)	0.0116 (2)	0.21721 (5)	0.0485 (3)
H5	0.218782	−0.153685	0.218778	0.058*
C6	0.40668 (12)	−0.0499 (3)	0.22744 (6)	0.0677 (5)
H6A	0.408156	−0.006072	0.256875	0.101*
H6B	0.398667	−0.211382	0.224883	0.101*
H6C	0.469652	−0.005757	0.218237	0.101*
C7	0.41087 (12)	0.0892 (3)	0.13812 (6)	0.0631 (4)
C8	0.44879 (16)	−0.0219 (5)	0.10551 (7)	0.0933 (7)
H8	0.422477	−0.162846	0.096242	0.112*
C9	0.5256 (2)	0.0747 (8)	0.08650 (9)	0.1305 (13)
H9	0.549227	−0.000456	0.064059	0.157*
C10	0.5670 (2)	0.2776 (8)	0.10007 (11)	0.1260 (13)
H10	0.619400	0.339895	0.087301	0.151*
C11	0.53136 (18)	0.3897 (5)	0.13259 (10)	0.1038 (8)
H11	0.559606	0.528631	0.142098	0.125*
C12	0.45310 (15)	0.2967 (4)	0.15145 (7)	0.0782 (6)
H12	0.428654	0.374833	0.173367	0.094*
C13	−0.01149 (11)	−0.0858 (3)	0.08867 (5)	0.0518 (4)
C14	−0.10124 (11)	0.0090 (3)	0.05961 (5)	0.0525 (4)
C15	−0.12826 (15)	0.2228 (3)	0.06286 (6)	0.0742 (5)
H15A	−0.185104	0.279718	0.044785	0.089*
H15B	−0.090481	0.316592	0.083223	0.089*
C16	−0.15837 (12)	−0.1489 (3)	0.02779 (5)	0.0564 (4)
C17	−0.10977 (16)	−0.2729 (4)	−0.00014 (5)	0.0708 (5)
H17	−0.039023	−0.262514	0.001575	0.085*
C18	−0.1648 (2)	−0.4116 (4)	−0.03050 (7)	0.0958 (8)
H18	−0.130994	−0.493464	−0.049229	0.115*
C19	−0.2677 (3)	−0.4298 (5)	−0.03334 (8)	0.1134 (10)
H19	−0.304484	−0.523105	−0.054083	0.136*
C20	−0.3175 (2)	−0.3114 (6)	−0.00582 (9)	0.1157 (10)
H20	−0.388066	−0.325807	−0.007462	0.139*
C21	−0.26323 (14)	−0.1701 (5)	0.02451 (7)	0.0876 (7)
H21	−0.297792	−0.088081	0.042958	0.105*
C22	0.03109 (12)	0.0142 (3)	0.20437 (6)	0.0672 (5)
H22A	0.028268	0.078936	0.232114	0.101*
H22B	−0.028940	0.057586	0.184710	0.101*
H22C	0.033936	−0.148016	0.206701	0.101*
C23	0.12310 (14)	0.3598 (3)	0.18558 (6)	0.0634 (4)
H23A	0.121449	0.420168	0.213756	0.095*
H23B	0.182901	0.414792	0.175117	0.095*
H23C	0.062811	0.406964	0.166470	0.095*
C24	0.23188 (12)	0.1029 (3)	0.26259 (5)	0.0561 (4)
C25	0.19071 (14)	−0.0174 (4)	0.29329 (6)	0.0799 (6)
H25	0.161466	−0.158856	0.286507	0.096*
C26	0.19262 (19)	0.0714 (7)	0.33434 (8)	0.1145 (11)
H26	0.162999	−0.008895	0.354612	0.137*
C27	0.2381 (2)	0.2771 (8)	0.34496 (9)	0.1189 (12)
H27	0.239505	0.335912	0.372438	0.143*
C28	0.2812 (2)	0.3951 (5)	0.31534 (8)	0.0972 (8)
H28	0.312974	0.533335	0.322796	0.117*
C29	0.27811 (15)	0.3109 (3)	0.27429 (6)	0.0705 (5)
H29	0.307183	0.393851	0.254201	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0508 (6)	0.0468 (6)	0.0766 (7)	0.0009 (5)	−0.0178 (5)	−0.0037 (5)
O2	0.1007 (10)	0.0557 (8)	0.0928 (10)	0.0142 (7)	−0.0415 (8)	−0.0174 (7)
N1	0.0407 (6)	0.0533 (7)	0.0568 (7)	−0.0003 (5)	−0.0017 (5)	0.0011 (6)
C1	0.0486 (8)	0.0503 (9)	0.0638 (9)	0.0032 (7)	0.0002 (7)	−0.0031 (7)
C2	0.0496 (8)	0.0642 (10)	0.0588 (9)	0.0016 (7)	−0.0033 (7)	−0.0036 (8)
C3	0.0428 (7)	0.0413 (8)	0.0664 (9)	0.0017 (6)	−0.0098 (6)	−0.0019 (7)
C4	0.0417 (7)	0.0390 (7)	0.0645 (9)	−0.0008 (6)	−0.0020 (6)	−0.0011 (6)
C5	0.0431 (7)	0.0375 (7)	0.0622 (8)	−0.0021 (6)	0.0000 (6)	0.0019 (6)
C6	0.0457 (8)	0.0804 (12)	0.0723 (11)	0.0086 (8)	−0.0046 (7)	0.0084 (9)
C7	0.0442 (8)	0.0781 (12)	0.0647 (10)	0.0083 (8)	0.0020 (7)	0.0031 (9)
C8	0.0619 (11)	0.133 (2)	0.0858 (14)	0.0136 (13)	0.0135 (10)	−0.0206 (14)
C9	0.0649 (15)	0.236 (4)	0.0952 (18)	0.021 (2)	0.0280 (13)	−0.007 (2)
C10	0.0565 (14)	0.212 (4)	0.111 (2)	0.0020 (19)	0.0203 (14)	0.056 (2)
C11	0.0638 (13)	0.116 (2)	0.131 (2)	−0.0098 (13)	0.0130 (14)	0.0376 (17)
C12	0.0596 (10)	0.0799 (14)	0.0959 (14)	−0.0054 (10)	0.0141 (10)	0.0095 (11)
C13	0.0477 (8)	0.0516 (9)	0.0535 (8)	−0.0001 (7)	−0.0004 (6)	−0.0047 (7)
C14	0.0441 (7)	0.0599 (9)	0.0520 (8)	0.0031 (7)	0.0030 (6)	0.0002 (7)
C15	0.0654 (11)	0.0712 (12)	0.0792 (12)	0.0136 (9)	−0.0098 (9)	−0.0016 (10)
C16	0.0502 (8)	0.0694 (10)	0.0462 (8)	0.0009 (7)	−0.0027 (6)	0.0016 (7)
C17	0.0755 (12)	0.0803 (13)	0.0535 (9)	0.0080 (10)	0.0012 (8)	−0.0048 (9)
C18	0.126 (2)	0.0941 (16)	0.0582 (11)	0.0157 (15)	−0.0134 (12)	−0.0170 (11)
C19	0.130 (2)	0.113 (2)	0.0787 (15)	−0.0208 (18)	−0.0422 (15)	−0.0145 (14)
C20	0.0711 (14)	0.157 (3)	0.1056 (19)	−0.0240 (16)	−0.0276 (13)	−0.0177 (19)
C21	0.0515 (10)	0.1270 (19)	0.0786 (12)	−0.0030 (11)	−0.0071 (9)	−0.0169 (12)
C22	0.0451 (8)	0.0701 (11)	0.0842 (12)	−0.0022 (8)	0.0041 (8)	0.0017 (9)
C23	0.0632 (10)	0.0438 (9)	0.0768 (11)	0.0056 (7)	−0.0087 (8)	−0.0018 (8)
C24	0.0465 (8)	0.0604 (10)	0.0587 (9)	0.0047 (7)	0.0001 (6)	0.0037 (7)
C25	0.0568 (10)	0.1088 (17)	0.0729 (12)	0.0005 (10)	0.0063 (9)	0.0203 (12)
C26	0.0678 (14)	0.208 (4)	0.0691 (14)	0.0195 (19)	0.0144 (11)	0.0227 (18)
C27	0.0841 (17)	0.198 (4)	0.0686 (15)	0.051 (2)	−0.0054 (13)	−0.030 (2)
C28	0.0943 (16)	0.1037 (18)	0.0817 (15)	0.0283 (14)	−0.0223 (13)	−0.0331 (13)
C29	0.0712 (11)	0.0642 (11)	0.0700 (11)	0.0039 (9)	−0.0075 (9)	−0.0096 (9)

Geometric parameters (Å, º) top

O1—C13	1.3268 (18)	C13—C14	1.487 (2)
O1—C3	1.4566 (17)	C14—C15	1.319 (2)
O2—C13	1.198 (2)	C14—C16	1.484 (2)
N1—C1	1.469 (2)	C15—H15A	0.9300
N1—C6	1.471 (2)	C15—H15B	0.9300
N1—C5	1.4768 (19)	C16—C21	1.379 (2)
C1—C7	1.511 (2)	C16—C17	1.379 (2)
C1—C2	1.526 (2)	C17—C18	1.375 (3)
C1—H1	0.9800	C17—H17	0.9300
C2—C3	1.504 (2)	C18—C19	1.354 (4)
C2—H2A	0.9700	C18—H18	0.9300
C2—H2B	0.9700	C19—C20	1.361 (4)
C3—C4	1.520 (2)	C19—H19	0.9300
C3—H3	0.9800	C20—C21	1.380 (3)
C4—C22	1.527 (2)	C20—H20	0.9300
C4—C23	1.532 (2)	C21—H21	0.9300
C4—C5	1.5593 (19)	C22—H22A	0.9600
C5—C24	1.516 (2)	C22—H22B	0.9600
C5—H5	0.9800	C22—H22C	0.9600
C6—H6A	0.9600	C23—H23A	0.9600
C6—H6B	0.9600	C23—H23B	0.9600
C6—H6C	0.9600	C23—H23C	0.9600
C7—C8	1.378 (3)	C24—C25	1.379 (3)
C7—C12	1.382 (3)	C24—C29	1.394 (2)
C8—C9	1.381 (4)	C25—C26	1.392 (4)
C8—H8	0.9300	C25—H25	0.9300
C9—C10	1.357 (5)	C26—C27	1.372 (5)
C9—H9	0.9300	C26—H26	0.9300
C10—C11	1.365 (5)	C27—C28	1.360 (4)
C10—H10	0.9300	C27—H27	0.9300
C11—C12	1.386 (3)	C28—C29	1.380 (3)
C11—H11	0.9300	C28—H28	0.9300
C12—H12	0.9300	C29—H29	0.9300

C13—O1—C3	117.78 (12)	O2—C13—O1	123.16 (14)
C1—N1—C6	108.09 (13)	O2—C13—C14	123.83 (14)
C1—N1—C5	114.69 (11)	O1—C13—C14	112.98 (13)
C6—N1—C5	109.24 (12)	C15—C14—C16	122.53 (15)
N1—C1—C7	111.29 (13)	C15—C14—C13	120.74 (15)
N1—C1—C2	112.27 (13)	C16—C14—C13	116.73 (14)
C7—C1—C2	107.75 (14)	C14—C15—H15A	120.0
N1—C1—H1	108.5	C14—C15—H15B	120.0
C7—C1—H1	108.5	H15A—C15—H15B	120.0
C2—C1—H1	108.5	C21—C16—C17	117.98 (17)
C3—C2—C1	110.60 (14)	C21—C16—C14	120.31 (16)
C3—C2—H2A	109.5	C17—C16—C14	121.68 (15)
C1—C2—H2A	109.5	C18—C17—C16	120.7 (2)
C3—C2—H2B	109.5	C18—C17—H17	119.6
C1—C2—H2B	109.5	C16—C17—H17	119.6
H2A—C2—H2B	108.1	C19—C18—C17	120.5 (2)
O1—C3—C2	108.26 (13)	C19—C18—H18	119.8
O1—C3—C4	109.16 (12)	C17—C18—H18	119.8
C2—C3—C4	111.78 (12)	C18—C19—C20	120.0 (2)
O1—C3—H3	109.2	C18—C19—H19	120.0
C2—C3—H3	109.2	C20—C19—H19	120.0
C4—C3—H3	109.2	C19—C20—C21	120.0 (2)
C3—C4—C22	108.46 (13)	C19—C20—H20	120.0
C3—C4—C23	111.67 (14)	C21—C20—H20	120.0
C22—C4—C23	109.15 (14)	C16—C21—C20	120.8 (2)
C3—C4—C5	105.45 (12)	C16—C21—H21	119.6
C22—C4—C5	109.82 (13)	C20—C21—H21	119.6
C23—C4—C5	112.19 (12)	C4—C22—H22A	109.5
N1—C5—C24	109.76 (12)	C4—C22—H22B	109.5
N1—C5—C4	113.32 (12)	H22A—C22—H22B	109.5
C24—C5—C4	111.28 (12)	C4—C22—H22C	109.5
N1—C5—H5	107.4	H22A—C22—H22C	109.5
C24—C5—H5	107.4	H22B—C22—H22C	109.5
C4—C5—H5	107.4	C4—C23—H23A	109.5
N1—C6—H6A	109.5	C4—C23—H23B	109.5
N1—C6—H6B	109.5	H23A—C23—H23B	109.5
H6A—C6—H6B	109.5	C4—C23—H23C	109.5
N1—C6—H6C	109.5	H23A—C23—H23C	109.5
H6A—C6—H6C	109.5	H23B—C23—H23C	109.5
H6B—C6—H6C	109.5	C25—C24—C29	118.22 (18)
C8—C7—C12	118.1 (2)	C25—C24—C5	120.39 (17)
C8—C7—C1	119.70 (19)	C29—C24—C5	121.38 (15)
C12—C7—C1	122.07 (17)	C24—C25—C26	120.5 (3)
C7—C8—C9	120.4 (3)	C24—C25—H25	119.8
C7—C8—H8	119.8	C26—C25—H25	119.8
C9—C8—H8	119.8	C27—C26—C25	120.1 (3)
C10—C9—C8	121.0 (3)	C27—C26—H26	119.9
C10—C9—H9	119.5	C25—C26—H26	119.9
C8—C9—H9	119.5	C28—C27—C26	120.0 (2)
C9—C10—C11	119.6 (3)	C28—C27—H27	120.0
C9—C10—H10	120.2	C26—C27—H27	120.0
C11—C10—H10	120.2	C27—C28—C29	120.4 (3)
C10—C11—C12	120.0 (3)	C27—C28—H28	119.8
C10—C11—H11	120.0	C29—C28—H28	119.8
C12—C11—H11	120.0	C28—C29—C24	120.7 (2)
C7—C12—C11	120.9 (2)	C28—C29—H29	119.6
C7—C12—H12	119.6	C24—C29—H29	119.6
C11—C12—H12	119.6

C6—N1—C1—C7	−68.92 (17)	C9—C10—C11—C12	−0.2 (4)
C5—N1—C1—C7	168.96 (12)	C8—C7—C12—C11	−0.1 (3)
C6—N1—C1—C2	170.20 (14)	C1—C7—C12—C11	−175.15 (19)
C5—N1—C1—C2	48.08 (18)	C10—C11—C12—C7	0.7 (4)
N1—C1—C2—C3	−51.25 (19)	C3—O1—C13—O2	2.1 (2)
C7—C1—C2—C3	−174.15 (14)	C3—O1—C13—C14	−179.60 (13)
C13—O1—C3—C2	102.68 (16)	O2—C13—C14—C15	173.29 (19)
C13—O1—C3—C4	−135.44 (14)	O1—C13—C14—C15	−5.0 (2)
C1—C2—C3—O1	−179.58 (12)	O2—C13—C14—C16	−5.9 (2)
C1—C2—C3—C4	60.16 (17)	O1—C13—C14—C16	175.90 (13)
O1—C3—C4—C22	62.12 (16)	C15—C14—C16—C21	−50.8 (3)
C2—C3—C4—C22	−178.14 (13)	C13—C14—C16—C21	128.38 (19)
O1—C3—C4—C23	−58.19 (16)	C15—C14—C16—C17	127.2 (2)
C2—C3—C4—C23	61.55 (16)	C13—C14—C16—C17	−53.7 (2)
O1—C3—C4—C5	179.71 (11)	C21—C16—C17—C18	0.5 (3)
C2—C3—C4—C5	−60.55 (15)	C14—C16—C17—C18	−177.43 (18)
C1—N1—C5—C24	−177.09 (12)	C16—C17—C18—C19	−0.4 (4)
C6—N1—C5—C24	61.42 (16)	C17—C18—C19—C20	−0.4 (4)
C1—N1—C5—C4	−52.00 (17)	C18—C19—C20—C21	1.0 (5)
C6—N1—C5—C4	−173.50 (13)	C17—C16—C21—C20	0.1 (3)
C3—C4—C5—N1	55.93 (15)	C14—C16—C21—C20	178.1 (2)
C22—C4—C5—N1	172.60 (13)	C19—C20—C21—C16	−0.9 (4)
C23—C4—C5—N1	−65.83 (17)	N1—C5—C24—C25	−142.18 (15)
C3—C4—C5—C24	−179.80 (12)	C4—C5—C24—C25	91.57 (18)
C22—C4—C5—C24	−63.13 (17)	N1—C5—C24—C29	39.07 (19)
C23—C4—C5—C24	58.43 (18)	C4—C5—C24—C29	−87.18 (17)
N1—C1—C7—C8	153.59 (17)	C29—C24—C25—C26	2.1 (3)
C2—C1—C7—C8	−82.9 (2)	C5—C24—C25—C26	−176.69 (18)
N1—C1—C7—C12	−31.4 (2)	C24—C25—C26—C27	−1.8 (3)
C2—C1—C7—C12	92.05 (19)	C25—C26—C27—C28	0.2 (4)
C12—C7—C8—C9	−1.0 (3)	C26—C27—C28—C29	1.0 (4)
C1—C7—C8—C9	174.1 (2)	C27—C28—C29—C24	−0.7 (3)
C7—C8—C9—C10	1.6 (4)	C25—C24—C29—C28	−0.9 (3)
C8—C9—C10—C11	−0.9 (5)	C5—C24—C29—C28	177.91 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C16–C21 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···N1	0.93	2.56	2.869 (2)	100
C3—H3···O2	0.98	2.26	2.677 (2)	104
C15—H15B···O1	0.93	2.34	2.683 (2)	101
C22—H22B···O1	0.96	2.53	2.878 (2)	102
C23—H23C···O1	0.96	2.57	2.903 (2)	100
C18—H18···O2ⁱ	0.93	2.55	3.473 (3)	170
C15—H15A···Cgⁱⁱ	0.93	2.94	3.613 (2)	130

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

Footnotes

‡Additional correspondence author, e-mail: [email protected]

Acknowledgements

The authors thank the Single Crystal XRD Facility at VIT, Vellore, Tamil Nadu, India, for providing the instrumentation and support necessary for this study.

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