(Z)-1-(1,3-Diphenyl-1H-pyrazol-4-yl)-N-phenyl­methanimine N-oxide

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Said, A.I.; Hawaiz, F.E.; Elgarhy, S.M.I.

doi:10.1107/S2414314618002080

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 2| February 2018| x180208

https://doi.org/10.1107/S2414314618002080

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(Z)-1-(1,3-Diphenyl-1H-pyrazol-4-yl)-N-phenylmethanimine N-oxide

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Awad I. Said,^e Farouq E. Hawaiz ^f ^* and Sahar M. I. Elgarhy ^g

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Assuit University, Egypt, ^fChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq, and ^gFaculty of Science, Department of Bio Chemistry, Beni Suef University, Beni Suef, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 February 2018; accepted 3 February 2018; online 7 February 2018)

In the title nitrone, C₂₂H₁₇N₃O, the dihedral angles between the central pyrazole ring and pendant N-bound, C-bound and nitrone-bound phenyl rings are 20.93 (6), 41.27 (6), and 32.57 (6)°, respectively. In the crystal, (101) layers are generated by C—H⋯O hydrogen bonds coupled with C—H⋯π(ring) and offset π–π stacking interactions.

Keywords: crystal structure; pyrazole; N-oxide; hydrogen bond; π–π stacking; nitrones.

CCDC reference: 1821805

Structure description

Nitrones have various uses including as spin-trap reagents (Villamena et al., 2007 ) and therapeutic agents (Piperno et al., 2010 ). They react in [3 + 2] dipolar cycloadditions with carious dipolarophiles to construct functionalized isoxazolidines, which are useful intermediates in organic synthesis (Dell, 1998 ). As part of our studies in this area, we report herein the synthesis and crystal structure of the title compound (Fig. 1).

Figure 1
The title molecule, shown with 50% probability displacement ellipsoids.

The dihedral angle between the pyrazole and the C4–C9 rings is 41.27 (6)°; those between the pyrazole and the C11–C16 and C17–C22 rings are, respectively, 32.57 (6) and 20.93 (6)°.

In the crystal, zigzag chains along the c-axis direction are generated by C6—H6⋯O1 and C7—H7⋯O1 hydrogen bonds (Table 1 and Figs. 2 and 3). These are connected into layers parallel to the ac plane by C5—H5⋯O1 hydrogen bonds, three C—H⋯π(ring) interactions (Table 1) and offset π–π stacking interactions between inversion-related C17–C22 rings [centroid–centroid distance = 3.6187 (8) Å](Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are, respectively, the centroids of the C4–C9 and C11–C16 benzene rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.979 (15)	2.303 (15)	3.2561 (14)	164.1 (11)
C6—H6⋯O1ⁱⁱ	0.988 (15)	2.514 (15)	3.1746 (14)	124.1 (11)
C7—H7⋯O1ⁱⁱ	1.003 (15)	2.544 (15)	3.1837 (14)	121.4 (11)
C9—H9⋯Cg3ⁱⁱⁱ	0.975 (14)	2.764 (14)	3.6409 (13)	152.8 (11)
C14—H14⋯Cg2^iv	0.988 (17)	2.884 (16)	3.6249 (14)	132.5 (12)
C19—H19⋯Cg2ⁱ	1.003 (17)	2.678 (17)	3.6128 (14)	155.3 (12)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x, y+1, z.

Figure 2
Details of the intermolecular interactions. C—H⋯O hydrogen bonds are shown by black dashed lines while C—H⋯π(ring) and offset π–π stacking interactions are shown, respectively, by green and orange dashed lines.

Figure 3
Packing viewed along the a-axis direction, with intermolecular interactions shown as depicted in Fig. 2

Synthesis and crystallization

A solution of (20 g, 0.08 mol) 1,3-diphenyl 4-formyl pyrazole in ethanol (20 ml) was added to a solution of (9.0 g, 0.08 mol) N-phenylhydroxyamine in ethanol (50 ml) and the mixture was heated under reflux for 2 h. The product was separated in 92% yield (25 g) and recrystallized from ethanol solution to afford colourless slabs; m.p. 431 K.

FTIR (KBr) (cm⁻¹): 3150 (Ar. C—H), 3050 (H—C=N+), 1597 (C=N), 1579 (C=N⁺). ¹H-NMR spectrum: δ p.p.m. (400 MHz, CDCl₃) 7.3–8.1 (m, 16H, Ar H), 9.9 (s, 1H, CH=N⁺). Proton decoupled ¹³C NMR spectrum: δ (100.5 MHz, CDCl₃) 113.2, 119.5, 127.2, 128.9, 129.0, 129.1, 129.3, 129.6, 129.8, 129.8, 132.3, 139.6, 147.9, 153.8 (15 Ar C). Mass spectrum (electron impact): e/m (%) 339.2 (1/2), 286.8 (100), 219.1 (58). Analysis calculated for (C₂₂H₁₇N₃O) (%): C 77.86, H 5.05, N 12.38. Found; C 77.27, H 5.02, N 12.38.

Refinement

Crystal and refinement details are presented in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₁₇N₃O
M_r	339.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	9.1084 (8), 10.8314 (9), 17.2226 (14)
β (°)	94.060 (3)
V (Å³)	1694.9 (2)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.66
Crystal size (mm)	0.24 × 0.21 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.85, 0.94
No. of measured, independent and observed [I > 2σ(I)] reflections	12691, 3366, 3115
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.086, 1.06
No. of reflections	3366
No. of parameters	304
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.19
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1821805

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618002080/hb4209sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618002080/hb4209Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618002080/hb4209Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(Z)-1-(1,3-Diphenyl-1H-pyrazol-4-yl)-N-phenylmethanimine N-oxide top

Crystal data top

C₂₂H₁₇N₃O	F(000) = 712
M_r = 339.38	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.1084 (8) Å	Cell parameters from 9914 reflections
b = 10.8314 (9) Å	θ = 4.8–74.6°
c = 17.2226 (14) Å	µ = 0.66 mm⁻¹
β = 94.060 (3)°	T = 150 K
V = 1694.9 (2) Å³	Slab, colourless
Z = 4	0.24 × 0.21 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3366 independent reflections
Radiation source: INCOATEC IµS micro-focus source	3115 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.028
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.6°, θ_min = 4.8°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −13→12
T_min = 0.85, T_max = 0.94	l = −21→19
12691 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	All H-atom parameters refined
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0366P)² + 0.5699P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3366 reflections	Δρ_max = 0.25 e Å⁻³
304 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL2016 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (4)

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
O1	0.28419 (9)	0.52663 (7)	0.36611 (4)	0.0258 (2)
N1	0.47211 (10)	0.17352 (8)	0.35347 (5)	0.0215 (2)
N2	0.43135 (10)	0.11254 (8)	0.28595 (5)	0.0224 (2)
N3	0.24264 (10)	0.51508 (8)	0.29270 (5)	0.0204 (2)
C1	0.34438 (12)	0.19128 (10)	0.24500 (6)	0.0210 (2)
C2	0.32853 (12)	0.30422 (10)	0.28615 (6)	0.0213 (2)
C3	0.41176 (12)	0.28765 (10)	0.35573 (6)	0.0225 (2)
H3	0.4284 (15)	0.3403 (13)	0.4012 (8)	0.033 (4)*
C4	0.28057 (12)	0.15709 (10)	0.16696 (6)	0.0209 (2)
C5	0.36634 (12)	0.09282 (10)	0.11610 (7)	0.0233 (2)
H5	0.4686 (16)	0.0721 (13)	0.1323 (8)	0.030 (4)*
C6	0.30717 (13)	0.06002 (10)	0.04264 (7)	0.0248 (2)
H6	0.3662 (16)	0.0143 (14)	0.0062 (9)	0.033 (4)*
C7	0.16261 (13)	0.08928 (11)	0.01886 (7)	0.0264 (3)
H7	0.1217 (16)	0.0663 (13)	−0.0348 (9)	0.032 (4)*
C8	0.07650 (13)	0.15151 (11)	0.06946 (7)	0.0278 (3)
H8	−0.0281 (17)	0.1681 (14)	0.0528 (9)	0.037 (4)*
C9	0.13483 (12)	0.18579 (10)	0.14310 (7)	0.0242 (2)
H9	0.0741 (16)	0.2279 (13)	0.1793 (8)	0.030 (3)*
C10	0.25703 (12)	0.41252 (10)	0.25391 (6)	0.0221 (2)
H10	0.2241 (15)	0.4182 (12)	0.1985 (8)	0.026 (3)*
C11	0.18754 (12)	0.62568 (10)	0.25287 (6)	0.0211 (2)
C12	0.07684 (13)	0.62002 (11)	0.19349 (7)	0.0266 (3)
H12	0.0327 (17)	0.5402 (15)	0.1778 (9)	0.041 (4)*
C13	0.02996 (15)	0.72902 (12)	0.15667 (7)	0.0320 (3)
H13	−0.0492 (18)	0.7239 (15)	0.1140 (10)	0.044 (4)*
C14	0.09319 (15)	0.84091 (12)	0.17922 (8)	0.0328 (3)
H14	0.0611 (18)	0.9174 (15)	0.1518 (9)	0.046 (4)*
C15	0.20296 (15)	0.84466 (11)	0.23889 (8)	0.0329 (3)
H15	0.2490 (18)	0.9228 (16)	0.2557 (9)	0.046 (4)*
C16	0.25028 (13)	0.73711 (11)	0.27657 (7)	0.0275 (3)
H16	0.3280 (16)	0.7378 (13)	0.3209 (9)	0.033 (4)*
C17	0.57182 (12)	0.11615 (10)	0.40996 (6)	0.0222 (2)
C18	0.58624 (13)	−0.01172 (11)	0.40974 (7)	0.0246 (2)
H18	0.5275 (16)	−0.0599 (13)	0.3711 (8)	0.030 (4)*
C19	0.68443 (14)	−0.06779 (12)	0.46408 (7)	0.0309 (3)
H19	0.6950 (17)	−0.1599 (16)	0.4635 (9)	0.042 (4)*
C20	0.76560 (14)	0.00264 (13)	0.51877 (8)	0.0358 (3)
H20	0.8351 (19)	−0.0370 (16)	0.5572 (10)	0.050 (5)*
C21	0.74840 (15)	0.12980 (13)	0.51930 (8)	0.0369 (3)
H21	0.803 (2)	0.1830 (17)	0.5598 (10)	0.055 (5)*
C22	0.65314 (14)	0.18760 (12)	0.46431 (7)	0.0307 (3)
H22	0.6438 (17)	0.2784 (15)	0.4628 (9)	0.039 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0310 (4)	0.0277 (4)	0.0179 (4)	0.0011 (3)	−0.0025 (3)	−0.0018 (3)
N1	0.0239 (5)	0.0209 (5)	0.0192 (4)	0.0005 (3)	−0.0005 (4)	0.0000 (3)
N2	0.0253 (5)	0.0216 (5)	0.0199 (4)	−0.0002 (3)	−0.0010 (4)	−0.0012 (3)
N3	0.0205 (5)	0.0211 (5)	0.0195 (4)	−0.0004 (3)	0.0009 (3)	0.0003 (3)
C1	0.0217 (5)	0.0199 (5)	0.0214 (5)	−0.0008 (4)	0.0019 (4)	0.0012 (4)
C2	0.0226 (5)	0.0202 (5)	0.0214 (5)	0.0001 (4)	0.0026 (4)	0.0003 (4)
C3	0.0252 (6)	0.0203 (5)	0.0219 (5)	0.0003 (4)	0.0020 (4)	−0.0007 (4)
C4	0.0238 (5)	0.0173 (5)	0.0213 (5)	−0.0013 (4)	0.0000 (4)	0.0015 (4)
C5	0.0227 (6)	0.0225 (5)	0.0245 (5)	0.0023 (4)	−0.0006 (4)	0.0008 (4)
C6	0.0281 (6)	0.0230 (5)	0.0230 (6)	0.0011 (4)	0.0016 (4)	−0.0012 (4)
C7	0.0302 (6)	0.0245 (6)	0.0237 (6)	−0.0018 (4)	−0.0047 (5)	−0.0001 (4)
C8	0.0237 (6)	0.0267 (6)	0.0321 (6)	0.0009 (4)	−0.0052 (5)	0.0000 (5)
C9	0.0229 (6)	0.0221 (5)	0.0278 (6)	0.0008 (4)	0.0022 (4)	−0.0010 (4)
C10	0.0240 (6)	0.0220 (5)	0.0201 (5)	0.0005 (4)	0.0015 (4)	0.0001 (4)
C11	0.0222 (5)	0.0208 (5)	0.0207 (5)	0.0021 (4)	0.0040 (4)	0.0012 (4)
C12	0.0287 (6)	0.0233 (6)	0.0272 (6)	0.0010 (4)	−0.0016 (5)	−0.0012 (4)
C13	0.0363 (7)	0.0300 (6)	0.0287 (6)	0.0057 (5)	−0.0037 (5)	0.0023 (5)
C14	0.0419 (7)	0.0241 (6)	0.0324 (6)	0.0057 (5)	0.0029 (5)	0.0059 (5)
C15	0.0381 (7)	0.0209 (6)	0.0395 (7)	−0.0015 (5)	0.0011 (5)	0.0005 (5)
C16	0.0283 (6)	0.0237 (6)	0.0301 (6)	−0.0009 (4)	−0.0003 (5)	−0.0013 (5)
C17	0.0208 (5)	0.0258 (6)	0.0198 (5)	0.0002 (4)	0.0011 (4)	0.0030 (4)
C18	0.0266 (6)	0.0261 (6)	0.0213 (5)	0.0034 (4)	0.0023 (4)	−0.0007 (4)
C19	0.0327 (7)	0.0313 (7)	0.0287 (6)	0.0086 (5)	0.0026 (5)	0.0037 (5)
C20	0.0297 (7)	0.0442 (7)	0.0323 (7)	0.0036 (5)	−0.0061 (5)	0.0094 (6)
C21	0.0337 (7)	0.0415 (7)	0.0336 (7)	−0.0096 (5)	−0.0102 (5)	0.0044 (6)
C22	0.0321 (6)	0.0283 (6)	0.0307 (6)	−0.0064 (5)	−0.0053 (5)	0.0022 (5)

Geometric parameters (Å, º) top

O1—N3	1.2999 (11)	C10—H10	0.982 (14)
N1—C3	1.3546 (14)	C11—C16	1.3845 (16)
N1—N2	1.3657 (12)	C11—C12	1.3857 (16)
N1—C17	1.4257 (13)	C12—C13	1.3927 (16)
N2—C1	1.3316 (14)	C12—H12	0.983 (16)
N3—C10	1.3076 (14)	C13—C14	1.3855 (18)
N3—C11	1.4523 (13)	C13—H13	0.994 (16)
C1—C2	1.4262 (15)	C14—C15	1.3828 (18)
C1—C4	1.4733 (14)	C14—H14	0.988 (17)
C2—C3	1.3836 (15)	C15—C16	1.3872 (17)
C2—C10	1.4343 (15)	C15—H15	0.980 (17)
C3—H3	0.973 (15)	C16—H16	1.003 (15)
C4—C9	1.3966 (16)	C17—C22	1.3875 (16)
C4—C5	1.3997 (16)	C17—C18	1.3912 (16)
C5—C6	1.3859 (16)	C18—C19	1.3878 (16)
C5—H5	0.979 (14)	C18—H18	0.976 (15)
C6—C7	1.3877 (17)	C19—C20	1.3846 (19)
C6—H6	0.988 (15)	C19—H19	1.003 (17)
C7—C8	1.3878 (17)	C20—C21	1.386 (2)
C7—H7	1.002 (14)	C20—H20	0.982 (17)
C8—C9	1.3903 (16)	C21—C22	1.3876 (17)
C8—H8	0.992 (15)	C21—H21	1.009 (18)
C9—H9	0.975 (14)	C22—H22	0.987 (16)

C3—N1—N2	112.30 (9)	C16—C11—C12	121.32 (10)
C3—N1—C17	128.19 (9)	C16—C11—N3	117.27 (10)
N2—N1—C17	119.47 (9)	C12—C11—N3	121.41 (10)
C1—N2—N1	104.89 (9)	C11—C12—C13	118.82 (11)
O1—N3—C10	123.09 (9)	C11—C12—H12	120.3 (9)
O1—N3—C11	116.56 (8)	C13—C12—H12	120.9 (9)
C10—N3—C11	120.21 (9)	C14—C13—C12	120.39 (11)
N2—C1—C2	111.32 (9)	C14—C13—H13	121.4 (9)
N2—C1—C4	120.24 (10)	C12—C13—H13	118.2 (9)
C2—C1—C4	128.43 (10)	C15—C14—C13	119.89 (11)
C3—C2—C1	104.51 (9)	C15—C14—H14	120.4 (9)
C3—C2—C10	130.34 (10)	C13—C14—H14	119.7 (9)
C1—C2—C10	124.64 (10)	C14—C15—C16	120.49 (12)
N1—C3—C2	106.98 (9)	C14—C15—H15	121.2 (10)
N1—C3—H3	121.2 (8)	C16—C15—H15	118.4 (10)
C2—C3—H3	131.8 (8)	C11—C16—C15	119.08 (11)
C9—C4—C5	119.18 (10)	C11—C16—H16	119.0 (8)
C9—C4—C1	121.19 (10)	C15—C16—H16	121.9 (8)
C5—C4—C1	119.62 (10)	C22—C17—C18	120.74 (11)
C6—C5—C4	120.04 (10)	C22—C17—N1	120.07 (10)
C6—C5—H5	120.1 (8)	C18—C17—N1	119.19 (10)
C4—C5—H5	119.8 (8)	C19—C18—C17	119.36 (11)
C5—C6—C7	120.69 (11)	C19—C18—H18	121.5 (8)
C5—C6—H6	120.9 (8)	C17—C18—H18	119.2 (8)
C7—C6—H6	118.4 (8)	C20—C19—C18	120.35 (12)
C6—C7—C8	119.49 (11)	C20—C19—H19	120.5 (9)
C6—C7—H7	119.9 (8)	C18—C19—H19	119.1 (9)
C8—C7—H7	120.6 (8)	C19—C20—C21	119.78 (12)
C7—C8—C9	120.41 (11)	C19—C20—H20	120.4 (10)
C7—C8—H8	118.7 (9)	C21—C20—H20	119.8 (10)
C9—C8—H8	120.9 (9)	C20—C21—C22	120.61 (12)
C8—C9—C4	120.19 (11)	C20—C21—H21	121.5 (10)
C8—C9—H9	120.7 (8)	C22—C21—H21	117.9 (10)
C4—C9—H9	119.1 (8)	C17—C22—C21	119.14 (12)
N3—C10—C2	123.79 (10)	C17—C22—H22	119.8 (9)
N3—C10—H10	114.1 (8)	C21—C22—H22	121.1 (9)
C2—C10—H10	121.8 (8)

C3—N1—N2—C1	0.49 (12)	C3—C2—C10—N3	−10.05 (19)
C17—N1—N2—C1	−177.46 (9)	C1—C2—C10—N3	179.52 (11)
N1—N2—C1—C2	0.02 (12)	O1—N3—C11—C16	33.72 (14)
N1—N2—C1—C4	179.05 (9)	C10—N3—C11—C16	−142.14 (11)
N2—C1—C2—C3	−0.49 (13)	O1—N3—C11—C12	−146.36 (10)
C4—C1—C2—C3	−179.42 (11)	C10—N3—C11—C12	37.78 (15)
N2—C1—C2—C10	171.98 (10)	C16—C11—C12—C13	0.83 (18)
C4—C1—C2—C10	−6.94 (18)	N3—C11—C12—C13	−179.08 (10)
N2—N1—C3—C2	−0.81 (13)	C11—C12—C13—C14	−0.01 (19)
C17—N1—C3—C2	176.91 (10)	C12—C13—C14—C15	−0.3 (2)
C1—C2—C3—N1	0.76 (12)	C13—C14—C15—C16	−0.1 (2)
C10—C2—C3—N1	−171.12 (11)	C12—C11—C16—C15	−1.28 (18)
N2—C1—C4—C9	138.67 (11)	N3—C11—C16—C15	178.64 (11)
C2—C1—C4—C9	−42.49 (17)	C14—C15—C16—C11	0.91 (19)
N2—C1—C4—C5	−40.22 (15)	C3—N1—C17—C22	−19.80 (17)
C2—C1—C4—C5	138.62 (12)	N2—N1—C17—C22	157.78 (11)
C9—C4—C5—C6	0.95 (16)	C3—N1—C17—C18	160.22 (11)
C1—C4—C5—C6	179.86 (10)	N2—N1—C17—C18	−22.20 (15)
C4—C5—C6—C7	−0.57 (17)	C22—C17—C18—C19	−0.72 (17)
C5—C6—C7—C8	−0.32 (18)	N1—C17—C18—C19	179.27 (10)
C6—C7—C8—C9	0.81 (18)	C17—C18—C19—C20	1.00 (18)
C7—C8—C9—C4	−0.42 (18)	C18—C19—C20—C21	0.1 (2)
C5—C4—C9—C8	−0.46 (17)	C19—C20—C21—C22	−1.6 (2)
C1—C4—C9—C8	−179.35 (10)	C18—C17—C22—C21	−0.69 (19)
O1—N3—C10—C2	−4.28 (17)	N1—C17—C22—C21	179.32 (11)
C11—N3—C10—C2	171.30 (10)	C20—C21—C22—C17	1.8 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are, respectively, the centroids of the C4–C9 and C11–C16 benzene rings.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.979 (15)	2.303 (15)	3.2561 (14)	164.1 (11)
C6—H6···O1ⁱⁱ	0.988 (15)	2.514 (15)	3.1746 (14)	124.1 (11)
C7—H7···O1ⁱⁱ	1.003 (15)	2.544 (15)	3.1837 (14)	121.4 (11)
C9—H9···Cg3ⁱⁱⁱ	0.975 (14)	2.764 (14)	3.6409 (13)	152.8 (11)
C14—H14···Cg2^iv	0.988 (17)	2.884 (16)	3.6249 (14)	132.5 (12)
C19—H19···Cg2ⁱ	1.003 (17)	2.678 (17)	3.6128 (14)	155.3 (12)

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

Funding information

The support of NSF–MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

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