2-Amino-4-(4-meth­oxy­phen­yl)-1-(4-methyl­phen­yl)-5-oxo-1,4,5,6,7,8-hexa­hydro­quinoline-3-carbo­nitrile

Tamam, A.H.A.; Kaur, M.; Akkurt, M.; Mohamed, S.K.; Jasinski, J.P.; Hussain, F.H.S.

doi:10.1107/S2414314618001670

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 2| February 2018| x180167

https://doi.org/10.1107/S2414314618001670

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2-Amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

Asmaa H. A. Tamam,^a Manpreet Kaur,^b Mehmet Akkurt,^c Shaaban K. Mohamed,^d,^e Jerry P. Jasinski ^b and Faiq H. S. Hussain ^f ^*

^aDepartment of Chemistry, Faculty of Science, Sohag University, Sohag, Egypt, ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^eChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and ^fResearch Center, University of Ishik, Erbil, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 18 January 2018; accepted 28 January 2018; online 2 February 2018)

In the title compound, C₂₄H₂₃N₃O₂, the cyclohexene and 1,4-dihydropyridine rings of the 1,4,5,6,7,8-hexahydroquinoline ring system each adopt a twisted-boat conformation. The dihedral angle between the benzene rings is 13.89 (10)°. In the crystal, molecules are linked through pairs of amino–nitrile N—H⋯N hydrogen bonds, forming inversion dimers. Weak C—H⋯O and C—H⋯π interactions connect the dimers, forming a three-dimensional network.

Keywords: crystal structure; hexahydroquinoline ring; dimers; hydroquinones; multicomponent reactions.

CCDC reference: 1820337

Structure description

Studies have shown that 1,4,5,6,7,8-hexahydroquinolines have significant cytotoxic activity against different human cancer cell lines (Mohamed et al., 2012 ; Al-Said et al., 2011 ; Alqasoumi et al., 2009 ). In recent years, hexahydroquinoline derivatives attracted more interest because of their biological and pharmacological activities, e.g. antimicrobial (Muli et al., 2014 ; Shah et al., 2012 ), antioxidant (Yang et al., 2011 ), antimalarial (Kalaria et al., 2014 ) and antiosteoporotic (Sashidhara et al., 2013 ). In addition, hexahydroquinolines have been used as calcium channel blockers for the treatment of cardiovascular diseases including hypertension (Joshi & Pawar, 2013 ; Gunduz et al., 2009 ; Aydin et al., 2006 ; Simsek et al., 2006 ).

As shown in Fig. 1, the cyclohexene (C4–C9) and 1,4-dihydropyridine (N1/C1–C4/C9) rings of the 1,4,5,6,7,8- hexahydroquinoline ring system (N1/C1–C9) each adopt a twisted-boat conformation [puckering parameters Q_T = 0.467 (2) Å, θ = 122.5 (2)°, φ = 354.0 (3)° and Q_T = 0.2541 (19) Å, θ = 106.6 (4)°, φ = 1.1 (5)°, respectively]. The methylbenzene and methoxybenzene rings form a dihedral angle of 13.89 (10)°. This angle is similar to the value of 11.52 (7)° found in the closely related structure of 2-amino-4-(4-chlorophenyl)-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile (Mohamed et al., 2015 ).

Figure 1
The title molecule, showing the atom-numbering scheme, with displacement ellipsoids drawn at the 50% probability level.

In the crystal, molecules are linked by pairs of N—H⋯N hydrogen bonds with an R₂²(12) ring motif (Table 1), forming centrosymmetric dimers (Fig. 2). These dimers are assembled into a three-dimensional network via C—H⋯O and C—H⋯π interactions.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 and Cg4 are the centroids of the C10–C15 and C16–C21 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N3ⁱ	0.86	2.31	3.016 (3)	140
C11—H11⋯O1ⁱⁱ	0.95	2.70	3.408 (2)	132
C21—H21⋯O1ⁱⁱ	0.95	2.68	3.433 (3)	136
C22—H22C⋯N3ⁱⁱⁱ	0.98	2.81	3.407 (4)	120
C23—H23B⋯O2^iv	0.98	2.76	3.484 (3)	131
C21—H21⋯Cg3^v	0.95	2.99	3.571 (2)	120
C22—H22B⋯Cg4^vi	0.98	2.92	3.695 (3)	137
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (vi) $[x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The molecular packing, viewed along the c axis, showing the intermolecular hydrogen bonds as dashed lines.

Synthesis and crystallization

To a solution of 1,3-cyclohexanedione (3.36 g, 0.03 mol) and p-toluidine (3.21 g, 0.03 mol) in ethanol (40 ml), a catalytic amount of triethylamine was added and the mixture was heated under reflux for 3 h. 4-Methoxybenzylidenemalononitrile (5.53 g, 0.03 mol) was added to the reaction mixture while refluxing for another 3 h. The reaction mixture was then cooled to room temperature. The precipitate that formed was filtered, dried and recrystallized from ethanol solution as orange crystals, yield 67%; m.p. 525 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. 28 reflections were omitted as clear outlier data.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₃N₃O₂
M_r	385.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.1066 (4), 19.6406 (9), 11.2901 (5)
β (°)	94.343 (4)
V (Å³)	2013.54 (16)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.66
Crystal size (mm)	0.38 × 0.28 × 0.22

Data collection
Diffractometer	Rigaku Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.813, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7397, 3793, 2933
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.149, 1.05
No. of reflections	3793
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.25
Computer programs: CrysAlis PRO (Rigaku Oxford Diffraction, 2015 $[Rigaku Oxford Diffraction (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2014 (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 1820337

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314618001670/ff4023sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618001670/ff4023Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

2-Amino-4-(4-methoxyphenyl)-1-(4-methylphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile top

Crystal data top

C₂₄H₂₃N₃O₂	F(000) = 816
M_r = 385.45	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 9.1066 (4) Å	Cell parameters from 2845 reflections
b = 19.6406 (9) Å	θ = 4.0–71.1°
c = 11.2901 (5) Å	µ = 0.66 mm⁻¹
β = 94.343 (4)°	T = 173 K
V = 2013.54 (16) Å³	Irregular, orange
Z = 4	0.38 × 0.28 × 0.22 mm

Data collection top

Rigaku Oxford Diffraction [model name?] diffractometer	3793 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	2933 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.3°, θ_min = 4.5°
ω scans	h = −6→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	k = −19→23
T_min = 0.813, T_max = 1.000	l = −13→13
7397 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0752P)² + 0.4388P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3793 reflections	Δρ_max = 0.33 e Å⁻³
265 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints

Special details top

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

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

	x	y	z	U_iso*/U_eq
O1	0.46137 (17)	0.69821 (8)	0.77151 (12)	0.0500 (4)
O2	0.9254 (2)	0.90959 (8)	0.55490 (16)	0.0602 (4)
N1	0.52568 (18)	0.59661 (9)	0.39959 (14)	0.0402 (4)
N2	0.7293 (2)	0.52949 (10)	0.36461 (16)	0.0505 (5)
H2A	0.7936	0.5051	0.4054	0.061*
H2B	0.6629	0.5032	0.3309	0.061*
N3	0.9846 (2)	0.54847 (10)	0.61603 (17)	0.0531 (5)
C1	0.6661 (2)	0.57350 (9)	0.43835 (16)	0.0365 (4)
C2	0.7304 (2)	0.59502 (9)	0.54430 (16)	0.0344 (4)
C3	0.6644 (2)	0.65027 (9)	0.61721 (15)	0.0338 (4)
H3	0.6793	0.6369	0.7028	0.041*
C4	0.5003 (2)	0.65333 (9)	0.58438 (16)	0.0358 (4)
C5	0.4081 (2)	0.68142 (10)	0.67280 (18)	0.0410 (4)
C6	0.2453 (2)	0.68749 (14)	0.6401 (2)	0.0557 (6)
H6A	0.2061	0.7268	0.6825	0.067*
H6B	0.1953	0.6460	0.6664	0.067*
C7	0.2102 (2)	0.69671 (13)	0.5074 (2)	0.0557 (6)
H7A	0.2479	0.7414	0.4826	0.067*
H7B	0.1022	0.6962	0.4893	0.067*
C8	0.2800 (2)	0.64023 (12)	0.43862 (19)	0.0482 (5)
H8A	0.2273	0.5970	0.4506	0.058*
H8B	0.2697	0.6511	0.3528	0.058*
C9	0.4407 (2)	0.63125 (10)	0.47773 (17)	0.0381 (4)
C10	0.7382 (2)	0.71933 (9)	0.60276 (15)	0.0334 (4)
C11	0.7090 (2)	0.75732 (10)	0.49983 (16)	0.0421 (5)
H11	0.6434	0.7399	0.4377	0.051*
C12	0.7741 (3)	0.82000 (10)	0.48682 (18)	0.0472 (5)
H12	0.7530	0.8454	0.4160	0.057*
C13	0.8699 (2)	0.84605 (10)	0.57628 (19)	0.0439 (5)
C14	0.9020 (2)	0.80888 (11)	0.67871 (19)	0.0465 (5)
H14	0.9684	0.8262	0.7404	0.056*
C15	0.8356 (2)	0.74549 (10)	0.69038 (17)	0.0415 (4)
H15	0.8580	0.7197	0.7606	0.050*
C16	0.4724 (2)	0.58466 (10)	0.27725 (16)	0.0377 (4)
C17	0.4055 (2)	0.52317 (10)	0.24530 (18)	0.0440 (5)
H17	0.3950	0.4888	0.3033	0.053*
C18	0.3542 (3)	0.51228 (11)	0.1284 (2)	0.0493 (5)
H18	0.3111	0.4696	0.1063	0.059*
C19	0.3643 (2)	0.56241 (12)	0.04289 (18)	0.0465 (5)
C20	0.4346 (2)	0.62267 (11)	0.07619 (19)	0.0471 (5)
H20	0.4450	0.6571	0.0183	0.057*
C21	0.4898 (2)	0.63388 (10)	0.19185 (19)	0.0442 (5)
H21	0.5395	0.6752	0.2126	0.053*
C22	1.0145 (3)	0.93964 (14)	0.6489 (3)	0.0714 (8)
H22A	1.0443	0.9853	0.6254	0.107*
H22B	1.1024	0.9116	0.6668	0.107*
H22C	0.9587	0.9428	0.7196	0.107*
C23	0.2984 (3)	0.55176 (15)	−0.0820 (2)	0.0655 (7)
H23A	0.2000	0.5722	−0.0907	0.098*
H23B	0.2910	0.5029	−0.0988	0.098*
H23C	0.3612	0.5733	−0.1380	0.098*
C24	0.8710 (2)	0.56923 (9)	0.58305 (17)	0.0382 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0454 (8)	0.0660 (9)	0.0386 (7)	−0.0022 (7)	0.0023 (6)	−0.0111 (7)
O2	0.0724 (11)	0.0429 (8)	0.0654 (10)	−0.0117 (8)	0.0065 (8)	0.0014 (7)
N1	0.0349 (8)	0.0502 (9)	0.0343 (8)	0.0089 (7)	−0.0056 (6)	−0.0083 (7)
N2	0.0458 (10)	0.0572 (10)	0.0466 (10)	0.0162 (8)	−0.0088 (8)	−0.0144 (8)
N3	0.0421 (10)	0.0568 (11)	0.0581 (11)	0.0144 (9)	−0.0115 (8)	−0.0075 (9)
C1	0.0336 (10)	0.0381 (9)	0.0371 (9)	0.0060 (7)	−0.0013 (7)	−0.0007 (7)
C2	0.0316 (9)	0.0349 (9)	0.0357 (9)	0.0037 (7)	−0.0035 (7)	0.0014 (7)
C3	0.0336 (9)	0.0382 (9)	0.0286 (8)	0.0025 (7)	−0.0034 (7)	0.0000 (7)
C4	0.0303 (9)	0.0405 (9)	0.0360 (9)	0.0011 (7)	−0.0010 (7)	−0.0013 (7)
C5	0.0366 (10)	0.0455 (10)	0.0408 (10)	−0.0016 (8)	0.0022 (8)	−0.0026 (8)
C6	0.0351 (11)	0.0765 (15)	0.0558 (13)	0.0034 (10)	0.0059 (9)	−0.0201 (12)
C7	0.0354 (11)	0.0706 (15)	0.0597 (13)	0.0117 (10)	−0.0049 (10)	−0.0143 (11)
C8	0.0324 (10)	0.0657 (13)	0.0451 (11)	0.0077 (9)	−0.0068 (8)	−0.0106 (10)
C9	0.0320 (10)	0.0439 (10)	0.0378 (9)	0.0035 (8)	−0.0020 (7)	−0.0022 (8)
C10	0.0315 (9)	0.0371 (9)	0.0314 (8)	0.0043 (7)	0.0009 (7)	−0.0027 (7)
C11	0.0536 (12)	0.0398 (10)	0.0316 (9)	0.0038 (9)	−0.0060 (8)	−0.0026 (7)
C12	0.0633 (14)	0.0403 (10)	0.0375 (10)	0.0057 (9)	0.0010 (9)	0.0030 (8)
C13	0.0467 (11)	0.0379 (10)	0.0479 (11)	0.0001 (8)	0.0089 (9)	−0.0024 (8)
C14	0.0403 (11)	0.0545 (12)	0.0437 (11)	−0.0078 (9)	−0.0036 (9)	−0.0047 (9)
C15	0.0387 (10)	0.0493 (11)	0.0355 (9)	−0.0012 (8)	−0.0035 (8)	0.0043 (8)
C16	0.0336 (9)	0.0431 (10)	0.0357 (9)	0.0021 (8)	−0.0026 (7)	−0.0025 (7)
C17	0.0452 (11)	0.0409 (10)	0.0450 (11)	−0.0061 (8)	−0.0026 (9)	0.0063 (8)
C18	0.0514 (13)	0.0439 (11)	0.0513 (12)	−0.0087 (9)	−0.0038 (10)	−0.0053 (9)
C19	0.0422 (11)	0.0561 (12)	0.0406 (10)	0.0000 (9)	−0.0004 (9)	−0.0019 (9)
C20	0.0460 (12)	0.0511 (11)	0.0437 (11)	−0.0058 (9)	−0.0001 (9)	0.0095 (9)
C21	0.0439 (11)	0.0380 (10)	0.0494 (11)	−0.0071 (8)	−0.0043 (9)	0.0018 (8)
C22	0.0638 (17)	0.0592 (15)	0.090 (2)	−0.0223 (13)	−0.0006 (14)	−0.0020 (14)
C23	0.0625 (16)	0.0885 (18)	0.0436 (12)	−0.0079 (14)	−0.0076 (11)	−0.0030 (12)
C24	0.0376 (11)	0.0369 (9)	0.0390 (9)	0.0016 (8)	−0.0041 (8)	−0.0028 (7)

Geometric parameters (Å, º) top

O1—C5	1.227 (2)	C10—C11	1.390 (3)
O2—C13	1.375 (2)	C10—C15	1.377 (3)
O2—C22	1.416 (3)	C11—H11	0.9500
N1—C1	1.396 (2)	C11—C12	1.379 (3)
N1—C9	1.394 (2)	C12—H12	0.9500
N1—C16	1.448 (2)	C12—C13	1.382 (3)
N2—H2A	0.8618	C13—C14	1.380 (3)
N2—H2B	0.8621	C14—H14	0.9500
N2—C1	1.358 (2)	C14—C15	1.395 (3)
N3—C24	1.148 (3)	C15—H15	0.9500
C1—C2	1.359 (3)	C16—C17	1.388 (3)
C2—C3	1.514 (2)	C16—C21	1.383 (3)
C2—C24	1.414 (3)	C17—H17	0.9500
C3—H3	1.0000	C17—C18	1.383 (3)
C3—C4	1.513 (3)	C18—H18	0.9500
C3—C10	1.528 (3)	C18—C19	1.387 (3)
C4—C5	1.461 (3)	C19—C20	1.384 (3)
C4—C9	1.354 (3)	C19—C23	1.505 (3)
C5—C6	1.505 (3)	C20—H20	0.9500
C6—H6A	0.9900	C20—C21	1.381 (3)
C6—H6B	0.9900	C21—H21	0.9500
C6—C7	1.518 (3)	C22—H22A	0.9800
C7—H7A	0.9900	C22—H22B	0.9800
C7—H7B	0.9900	C22—H22C	0.9800
C7—C8	1.521 (3)	C23—H23A	0.9800
C8—H8A	0.9900	C23—H23B	0.9800
C8—H8B	0.9900	C23—H23C	0.9800
C8—C9	1.507 (3)

C13—O2—C22	116.38 (19)	C15—C10—C11	118.20 (18)
C1—N1—C16	118.64 (15)	C10—C11—H11	119.6
C9—N1—C1	119.96 (15)	C12—C11—C10	120.78 (18)
C9—N1—C16	121.40 (15)	C12—C11—H11	119.6
H2A—N2—H2B	109.2	C11—C12—H12	119.8
C1—N2—H2A	109.2	C11—C12—C13	120.35 (19)
C1—N2—H2B	109.7	C13—C12—H12	119.8
N2—C1—N1	115.82 (16)	O2—C13—C12	115.33 (19)
N2—C1—C2	124.27 (17)	O2—C13—C14	124.8 (2)
C2—C1—N1	119.91 (17)	C14—C13—C12	119.91 (19)
C1—C2—C3	122.61 (16)	C13—C14—H14	120.5
C1—C2—C24	118.73 (17)	C13—C14—C15	119.03 (19)
C24—C2—C3	118.42 (15)	C15—C14—H14	120.5
C2—C3—H3	107.9	C10—C15—C14	121.71 (18)
C2—C3—C10	112.45 (15)	C10—C15—H15	119.1
C4—C3—C2	108.71 (15)	C14—C15—H15	119.1
C4—C3—H3	107.9	C17—C16—N1	119.85 (18)
C4—C3—C10	111.90 (15)	C21—C16—N1	120.25 (18)
C10—C3—H3	107.9	C21—C16—C17	119.89 (18)
C5—C4—C3	117.12 (16)	C16—C17—H17	120.2
C9—C4—C3	121.81 (17)	C18—C17—C16	119.51 (19)
C9—C4—C5	121.07 (18)	C18—C17—H17	120.2
O1—C5—C4	120.93 (18)	C17—C18—H18	119.4
O1—C5—C6	121.09 (19)	C17—C18—C19	121.27 (19)
C4—C5—C6	117.97 (17)	C19—C18—H18	119.4
C5—C6—H6A	109.1	C18—C19—C23	120.7 (2)
C5—C6—H6B	109.1	C20—C19—C18	118.15 (19)
C5—C6—C7	112.41 (19)	C20—C19—C23	121.1 (2)
H6A—C6—H6B	107.9	C19—C20—H20	119.3
C7—C6—H6A	109.1	C21—C20—C19	121.40 (19)
C7—C6—H6B	109.1	C21—C20—H20	119.3
C6—C7—H7A	109.5	C16—C21—H21	120.2
C6—C7—H7B	109.5	C20—C21—C16	119.67 (18)
C6—C7—C8	110.6 (2)	C20—C21—H21	120.2
H7A—C7—H7B	108.1	O2—C22—H22A	109.5
C8—C7—H7A	109.5	O2—C22—H22B	109.5
C8—C7—H7B	109.5	O2—C22—H22C	109.5
C7—C8—H8A	109.3	H22A—C22—H22B	109.5
C7—C8—H8B	109.3	H22A—C22—H22C	109.5
H8A—C8—H8B	107.9	H22B—C22—H22C	109.5
C9—C8—C7	111.70 (17)	C19—C23—H23A	109.5
C9—C8—H8A	109.3	C19—C23—H23B	109.5
C9—C8—H8B	109.3	C19—C23—H23C	109.5
N1—C9—C8	116.42 (16)	H23A—C23—H23B	109.5
C4—C9—N1	120.99 (17)	H23A—C23—H23C	109.5
C4—C9—C8	122.56 (18)	H23B—C23—H23C	109.5
C11—C10—C3	120.53 (16)	N3—C24—C2	179.1 (2)
C15—C10—C3	121.27 (16)

Hydrogen-bond geometry (Å, º) top

Cg3 and Cg4 are the centroids of the C10–C15 and C16–C21 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N3ⁱ	0.86	2.31	3.016 (3)	140
C11—H11···O1ⁱⁱ	0.95	2.70	3.408 (2)	132
C21—H21···O1ⁱⁱ	0.95	2.68	3.433 (3)	136
C22—H22C···N3ⁱⁱⁱ	0.98	2.81	3.407 (4)	120
C23—H23B···O2^iv	0.98	2.76	3.484 (3)	131
C21—H21···Cg3^v	0.95	2.99	3.571 (2)	120
C22—H22B···Cg4^vi	0.98	2.92	3.695 (3)	137

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

Funding information

JPJ would like to acknowledge the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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