N′-[(1E)-1-(4-Chloro­phen­yl)ethyl­idene]-2-(2,3-di­methyl­anilino)benzohydrazide

Mohamed, S.K.; Jasinski, J.P.; Akkurt, M.; McGurk, E.A.; Albayati, M.R.; Mohamed, A.F.

doi:10.1107/S2414314617011889

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 8| August 2017| x171188

https://doi.org/10.1107/S2414314617011889

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N′-[(1E)-1-(4-Chlorophenyl)ethylidene]-2-(2,3-dimethylanilino)benzohydrazide

Shaaban K. Mohamed,^a,^b Jerry P. Jasinski,^c Mehmet Akkurt,^d Elizabeth A. McGurk,^c Mustafa R. Albayati ^e ^* and Alaa F. Mohamed ^f

^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, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eDepartment of Chemistry, College of Education, Kirkuk University, Kirkuk, Iraq, and ^fNational Organization for Drug Control and Research, Giza, Egypt
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 7 August 2017; accepted 16 August 2017; online 21 August 2017)

In the title compound, C₂₃H₂₂ClN₃O, the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings is 62.49 (10)°. These rings make dihedral angles of 21.11 (9) and 59.85 (9)°, respectively, with the central benzene ring. In the crystal, molecules are linked into a three-dimensional supramolecular network by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds, and weak C—H⋯π interactions.

Keywords: crystal structure; mefenamic acid; non-steroidal anti-inflammatory drug; NSAID; hydrazone.

CCDC reference: 1569207

Structure description

Mefenamic acid (MA), or 2-[(2,3-dimethylphenyl)amino]benzoic acid, belongs to the family of N-arylanthranilic acids. It is one of the most widely used non-steroidal anti-inflammatory drugs (NSAIDs), having both anti-inflammatory and analgesic activities (Arun & Ashok, 2009 ). NSAIDs are associated with gastrointestinal ulcers, serious cardiovascular events and hypertension (Gupta & Kulkarni, 2013 ). Recently, it was found that masking the carboxylic acid group in the parent drug of NSAIDs led to safer prodrug profiles and enhanced the pharmacophoric efficacy (Mague et al., 2014 ). In addition, some evidence showed that the hydrazone group present in the anti-inflammatory drug structure is behind its inhibitory character (Mohamed et al., 2012 ). Further to our ongoing study of the functionalization of NSAIDs (Mohamed et al., 2015a ,b ), the title compound was synthesized as a hydrazone profile incorporating MA as a core structure without a free carboxylic group.

The title molecule (Fig. 1) is twisted, with the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings being 62.49 (10)°. The chlorophenyl and dimethylphenyl rings make dihedral angles of 21.11 (9) and 59.85 (9)° with the central benzene ring, respectively. The bridging fragment (C1/N1/N2/O1/C8) is not planar, with an N1—N2—C8—O1 torsion angle of 5.0 (2)°. All bond lengths and angles (Table 1) are comparable with those of related structures (Zhen & Han, 2005 ; Chantrapromma et al., 2014 ; Fun et al., 2011 ; Horkaew et al., 2012 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C9–C14 and C15–C20 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.86 (2)	2.53 (2)	3.3194 (18)	153 (2)
N2—H2N⋯N1ⁱ	0.86 (2)	2.34 (2)	3.0563 (18)	141 (2)
N3—H3N⋯O1	0.86 (2)	1.99 (2)	2.691 (2)	139 (2)
C10—H10⋯O1ⁱ	0.95	2.51	3.278 (2)	138
C12—H12⋯Cg3ⁱⁱ	0.95	2.91	3.737 (2)	146
C21—H21C⋯Cg2ⁱⁱⁱ	0.98	2.94	3.720 (3)	138
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+2; (iii) -x, -y+1, -z+1.

Figure 1
The structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

In the crystal (Fig. 2), molecules are linked by N—H⋯N, N—H⋯O and C—H⋯O hydrogen bonds (Table 1) into a three-dimensional network. Weak C—H⋯π interactions (Table 1) are also present.

Figure 2
Part of the packing diagram for the title compound, viewing down the c axis.

Synthesis and crystallization

The title compound was synthesized according to our previously reported procedure (Mohamed et al., 2015a). The product was recrystallized from ethanol solution to yield yellow blocks of (I) (m.p. 473–477 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms on C atoms were placed in calculated positions and allowed to ride on their carrier atoms, with aromatic C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C), and methyl C—H = 0.98 Å and U_iso(H) = 1.5U_eq(C). H atoms on N atoms were found in a difference Fourier map and were refined, with the N—H distances restrained to 0.86 (2) Å and with U_iso(H) = 1.2U_eq(N).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₃H₂₂ClN₃O
M_r	391.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.1089 (4), 19.6738 (6), 7.9333 (2)
β (°)	96.899 (2)
V (Å³)	2031.20 (10)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.80
Crystal size (mm)	0.45 × 0.25 × 0.10

Data collection
Diffractometer	Rigaku Oxford Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.749, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7509, 3854, 3295
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.01
No. of reflections	3854
No. of parameters	262
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.40
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), PLATON (Spek, 2009 ) and WinGX (Farrugia, 2012).

Structural data

CCDC reference: 1569207

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617011889/xu4031sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011889/xu4031Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617011889/xu4031Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and WinGX (Farrugia, 2012).

N'-[(1E)-1-(4-Chlorophenyl)ethylidene]-2-(2,3-dimethylanilino)benzohydrazide top

Crystal data top

C₂₃H₂₂ClN₃O	F(000) = 824
M_r = 391.88	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.1089 (4) Å	Cell parameters from 3019 reflections
b = 19.6738 (6) Å	θ = 4.1–71.1°
c = 7.9333 (2) Å	µ = 1.80 mm⁻¹
β = 96.899 (2)°	T = 173 K
V = 2031.20 (10) Å³	Prism, colourless
Z = 4	0.45 × 0.25 × 0.10 mm

Data collection top

Rigaku Oxford Gemini diffractometer	3854 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	3295 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.4°, θ_min = 4.1°
ω scans	h = −15→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −23→9
T_min = 0.749, T_max = 1.000	l = −9→9
7509 measured reflections

Refinement top

Refinement on F²	2 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) = 0.132	w = 1/[σ²(F_o²) + (0.0717P)² + 0.6046P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3854 reflections	Δρ_max = 0.37 e Å⁻³
262 parameters	Δρ_min = −0.40 e Å⁻³

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
C1	0.38673 (13)	0.82927 (9)	0.6434 (2)	0.0373 (4)
C2	0.45079 (13)	0.84964 (9)	0.5093 (2)	0.0380 (4)
C3	0.51538 (14)	0.80264 (11)	0.4452 (2)	0.0450 (4)
H3A	0.5221	0.7583	0.4928	0.054*
C4	0.57021 (15)	0.82006 (13)	0.3121 (3)	0.0554 (5)
H4	0.6157	0.7884	0.2701	0.066*
C5	0.55760 (17)	0.88399 (14)	0.2419 (3)	0.0583 (6)
C6	0.49458 (18)	0.93127 (12)	0.3018 (3)	0.0574 (6)
H6	0.4866	0.9750	0.2510	0.069*
C7	0.44242 (16)	0.91431 (10)	0.4382 (2)	0.0478 (5)
H7	0.4004	0.9473	0.4836	0.057*
C8	0.24073 (13)	0.68585 (8)	0.70860 (18)	0.0315 (3)
C9	0.17766 (12)	0.65811 (8)	0.83703 (19)	0.0320 (3)
C10	0.12799 (13)	0.70152 (9)	0.9389 (2)	0.0353 (4)
H10	0.1363	0.7492	0.9281	0.042*
C11	0.06683 (14)	0.67704 (9)	1.0554 (2)	0.0397 (4)
H11	0.0332	0.7074	1.1236	0.048*
C12	0.05530 (14)	0.60724 (10)	1.0711 (2)	0.0413 (4)
H12	0.0145	0.5898	1.1525	0.050*
C13	0.10221 (14)	0.56296 (9)	0.9703 (2)	0.0384 (4)
H13	0.0934	0.5154	0.9834	0.046*
C14	0.16279 (13)	0.58687 (8)	0.8485 (2)	0.0343 (4)
C15	0.19282 (13)	0.47261 (8)	0.7284 (2)	0.0359 (4)
C16	0.22356 (15)	0.43079 (11)	0.8668 (2)	0.0477 (4)
H16	0.2523	0.4500	0.9716	0.057*
C17	0.21207 (16)	0.36117 (11)	0.8509 (3)	0.0533 (5)
H17	0.2322	0.3325	0.9454	0.064*
C18	0.17132 (16)	0.33337 (9)	0.6975 (3)	0.0509 (5)
H18	0.1636	0.2855	0.6878	0.061*
C19	0.14150 (15)	0.37399 (9)	0.5579 (3)	0.0435 (4)
C20	0.15184 (12)	0.44481 (8)	0.5730 (2)	0.0347 (4)
C21	0.1000 (2)	0.34189 (12)	0.3907 (3)	0.0730 (7)
H21A	0.1014	0.2923	0.4023	0.110*
H21B	0.1426	0.3555	0.3030	0.110*
H21C	0.0291	0.3570	0.3583	0.110*
C22	0.12136 (16)	0.49003 (10)	0.4219 (2)	0.0464 (4)
H22A	0.1805	0.4967	0.3590	0.070*
H22B	0.0985	0.5341	0.4608	0.070*
H22C	0.0653	0.4687	0.3475	0.070*
C23	0.3623 (2)	0.87996 (12)	0.7733 (3)	0.0633 (7)
H23A	0.3985	0.9226	0.7571	0.095*
H23B	0.3844	0.8622	0.8873	0.095*
H23C	0.2881	0.8883	0.7608	0.095*
Cl1	0.62355 (6)	0.90513 (5)	0.07017 (9)	0.0951 (3)
N1	0.35227 (10)	0.76846 (7)	0.62931 (16)	0.0322 (3)
N2	0.29092 (11)	0.74519 (7)	0.74680 (16)	0.0317 (3)
H2N	0.2954 (16)	0.7615 (10)	0.848 (2)	0.038*
N3	0.20736 (14)	0.54361 (8)	0.7410 (2)	0.0445 (4)
H3N	0.2270 (18)	0.5635 (11)	0.654 (2)	0.053*
O1	0.24471 (11)	0.65752 (6)	0.57097 (15)	0.0424 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0380 (8)	0.0442 (9)	0.0299 (8)	−0.0101 (7)	0.0051 (6)	−0.0016 (7)
C2	0.0337 (8)	0.0489 (10)	0.0317 (8)	−0.0158 (7)	0.0049 (6)	−0.0047 (7)
C3	0.0376 (9)	0.0576 (11)	0.0402 (9)	−0.0108 (8)	0.0059 (7)	−0.0053 (8)
C4	0.0373 (9)	0.0833 (15)	0.0475 (11)	−0.0155 (10)	0.0129 (8)	−0.0152 (11)
C5	0.0458 (11)	0.0896 (16)	0.0419 (10)	−0.0328 (11)	0.0151 (8)	−0.0010 (11)
C6	0.0599 (12)	0.0634 (13)	0.0506 (11)	−0.0254 (11)	0.0140 (10)	0.0083 (10)
C7	0.0498 (10)	0.0492 (10)	0.0463 (10)	−0.0161 (8)	0.0136 (8)	−0.0008 (8)
C8	0.0395 (8)	0.0310 (7)	0.0240 (7)	−0.0002 (6)	0.0043 (6)	0.0035 (6)
C9	0.0359 (8)	0.0362 (8)	0.0238 (7)	−0.0069 (6)	0.0026 (6)	0.0006 (6)
C10	0.0420 (9)	0.0348 (8)	0.0291 (7)	−0.0071 (7)	0.0038 (6)	−0.0025 (6)
C11	0.0436 (9)	0.0442 (9)	0.0328 (8)	−0.0043 (7)	0.0110 (7)	−0.0043 (7)
C12	0.0443 (9)	0.0493 (10)	0.0321 (8)	−0.0109 (8)	0.0115 (7)	0.0023 (7)
C13	0.0461 (9)	0.0366 (8)	0.0333 (8)	−0.0101 (7)	0.0073 (7)	0.0026 (7)
C14	0.0402 (8)	0.0356 (8)	0.0269 (7)	−0.0070 (7)	0.0034 (6)	−0.0008 (6)
C15	0.0376 (8)	0.0324 (8)	0.0387 (8)	−0.0022 (7)	0.0092 (7)	0.0021 (7)
C16	0.0487 (10)	0.0509 (10)	0.0420 (9)	−0.0057 (8)	−0.0006 (8)	0.0085 (8)
C17	0.0514 (11)	0.0458 (10)	0.0626 (13)	0.0074 (9)	0.0058 (9)	0.0233 (9)
C18	0.0529 (11)	0.0295 (8)	0.0730 (14)	0.0021 (8)	0.0186 (10)	0.0049 (9)
C19	0.0419 (9)	0.0353 (9)	0.0543 (11)	−0.0030 (7)	0.0092 (8)	−0.0044 (8)
C20	0.0296 (7)	0.0343 (8)	0.0407 (9)	0.0021 (6)	0.0069 (6)	0.0013 (7)
C21	0.0935 (19)	0.0511 (13)	0.0728 (16)	−0.0187 (13)	0.0027 (14)	−0.0197 (12)
C22	0.0506 (10)	0.0464 (10)	0.0416 (9)	0.0018 (8)	0.0026 (8)	0.0041 (8)
C23	0.0870 (17)	0.0562 (12)	0.0537 (12)	−0.0331 (12)	0.0376 (12)	−0.0182 (10)
Cl1	0.0815 (5)	0.1470 (8)	0.0648 (4)	−0.0449 (5)	0.0413 (3)	0.0049 (4)
N1	0.0324 (7)	0.0400 (7)	0.0243 (6)	−0.0044 (6)	0.0046 (5)	0.0042 (5)
N2	0.0372 (7)	0.0375 (7)	0.0210 (6)	−0.0062 (6)	0.0059 (5)	0.0020 (5)
N3	0.0661 (10)	0.0332 (7)	0.0379 (8)	−0.0106 (7)	0.0215 (7)	−0.0013 (6)
O1	0.0654 (8)	0.0355 (6)	0.0289 (6)	−0.0076 (6)	0.0161 (5)	−0.0023 (5)

Geometric parameters (Å, º) top

C1—N1	1.279 (2)	C13—H13	0.9500
C1—C2	1.487 (2)	C14—N3	1.383 (2)
C1—C23	1.496 (3)	C15—C16	1.392 (3)
C2—C3	1.391 (3)	C15—C20	1.396 (2)
C2—C7	1.391 (3)	C15—N3	1.412 (2)
C3—C4	1.390 (3)	C16—C17	1.382 (3)
C3—H3A	0.9500	C16—H16	0.9500
C4—C5	1.377 (4)	C17—C18	1.382 (3)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.366 (4)	C18—C19	1.384 (3)
C5—Cl1	1.749 (2)	C18—H18	0.9500
C6—C7	1.389 (3)	C19—C20	1.404 (2)
C6—H6	0.9500	C19—C21	1.510 (3)
C7—H7	0.9500	C20—C22	1.508 (2)
C8—O1	1.2325 (19)	C21—H21A	0.9800
C8—N2	1.356 (2)	C21—H21B	0.9800
C8—C9	1.491 (2)	C21—H21C	0.9800
C9—C10	1.390 (2)	C22—H22A	0.9800
C9—C14	1.419 (2)	C22—H22B	0.9800
C10—C11	1.381 (2)	C22—H22C	0.9800
C10—H10	0.9500	C23—H23A	0.9800
C11—C12	1.389 (3)	C23—H23B	0.9800
C11—H11	0.9500	C23—H23C	0.9800
C12—C13	1.377 (3)	N1—N2	1.3804 (18)
C12—H12	0.9500	N2—H2N	0.859 (15)
C13—C14	1.403 (2)	N3—H3N	0.861 (16)

N1—C1—C2	114.40 (15)	C16—C15—N3	120.34 (17)
N1—C1—C23	125.56 (16)	C20—C15—N3	118.98 (15)
C2—C1—C23	119.93 (16)	C17—C16—C15	119.74 (19)
C3—C2—C7	118.80 (17)	C17—C16—H16	120.1
C3—C2—C1	120.22 (17)	C15—C16—H16	120.1
C7—C2—C1	120.85 (17)	C18—C17—C16	119.91 (18)
C4—C3—C2	120.5 (2)	C18—C17—H17	120.0
C4—C3—H3A	119.8	C16—C17—H17	120.0
C2—C3—H3A	119.8	C17—C18—C19	121.24 (17)
C5—C4—C3	119.0 (2)	C17—C18—H18	119.4
C5—C4—H4	120.5	C19—C18—H18	119.4
C3—C4—H4	120.5	C18—C19—C20	119.34 (18)
C6—C5—C4	121.96 (19)	C18—C19—C21	119.94 (19)
C6—C5—Cl1	119.00 (19)	C20—C19—C21	120.71 (19)
C4—C5—Cl1	119.04 (19)	C15—C20—C19	119.15 (16)
C5—C6—C7	118.8 (2)	C15—C20—C22	120.55 (15)
C5—C6—H6	120.6	C19—C20—C22	120.29 (17)
C7—C6—H6	120.6	C19—C21—H21A	109.5
C6—C7—C2	120.9 (2)	C19—C21—H21B	109.5
C6—C7—H7	119.5	H21A—C21—H21B	109.5
C2—C7—H7	119.5	C19—C21—H21C	109.5
O1—C8—N2	121.07 (14)	H21A—C21—H21C	109.5
O1—C8—C9	121.73 (14)	H21B—C21—H21C	109.5
N2—C8—C9	117.16 (13)	C20—C22—H22A	109.5
C10—C9—C14	119.45 (15)	C20—C22—H22B	109.5
C10—C9—C8	120.62 (14)	H22A—C22—H22B	109.5
C14—C9—C8	119.81 (15)	C20—C22—H22C	109.5
C11—C10—C9	121.66 (16)	H22A—C22—H22C	109.5
C11—C10—H10	119.2	H22B—C22—H22C	109.5
C9—C10—H10	119.2	C1—C23—H23A	109.5
C10—C11—C12	118.90 (16)	C1—C23—H23B	109.5
C10—C11—H11	120.5	H23A—C23—H23B	109.5
C12—C11—H11	120.5	C1—C23—H23C	109.5
C13—C12—C11	120.82 (16)	H23A—C23—H23C	109.5
C13—C12—H12	119.6	H23B—C23—H23C	109.5
C11—C12—H12	119.6	C1—N1—N2	118.65 (14)
C12—C13—C14	121.14 (16)	C8—N2—N1	116.17 (13)
C12—C13—H13	119.4	C8—N2—H2N	120.5 (14)
C14—C13—H13	119.4	N1—N2—H2N	121.7 (14)
N3—C14—C13	122.27 (15)	C14—N3—C15	126.10 (15)
N3—C14—C9	119.78 (15)	C14—N3—H3N	113.8 (16)
C13—C14—C9	117.94 (15)	C15—N3—H3N	116.4 (16)
C16—C15—C20	120.61 (16)

N1—C1—C2—C3	−35.9 (2)	C8—C9—C14—N3	0.3 (2)
C23—C1—C2—C3	147.8 (2)	C10—C9—C14—C13	−3.4 (2)
N1—C1—C2—C7	139.95 (17)	C8—C9—C14—C13	−179.50 (15)
C23—C1—C2—C7	−36.4 (3)	C20—C15—C16—C17	−0.9 (3)
C7—C2—C3—C4	−0.2 (3)	N3—C15—C16—C17	−177.81 (18)
C1—C2—C3—C4	175.68 (16)	C15—C16—C17—C18	0.8 (3)
C2—C3—C4—C5	−1.6 (3)	C16—C17—C18—C19	0.0 (3)
C3—C4—C5—C6	1.5 (3)	C17—C18—C19—C20	−0.7 (3)
C3—C4—C5—Cl1	−178.09 (15)	C17—C18—C19—C21	178.3 (2)
C4—C5—C6—C7	0.5 (3)	C16—C15—C20—C19	0.3 (3)
Cl1—C5—C6—C7	−179.95 (16)	N3—C15—C20—C19	177.20 (16)
C5—C6—C7—C2	−2.4 (3)	C16—C15—C20—C22	−178.26 (17)
C3—C2—C7—C6	2.2 (3)	N3—C15—C20—C22	−1.3 (2)
C1—C2—C7—C6	−173.65 (17)	C18—C19—C20—C15	0.5 (3)
O1—C8—C9—C10	−144.71 (17)	C21—C19—C20—C15	−178.4 (2)
N2—C8—C9—C10	32.9 (2)	C18—C19—C20—C22	179.07 (18)
O1—C8—C9—C14	31.3 (2)	C21—C19—C20—C22	0.1 (3)
N2—C8—C9—C14	−151.01 (15)	C2—C1—N1—N2	−179.22 (14)
C14—C9—C10—C11	2.1 (2)	C23—C1—N1—N2	−3.2 (3)
C8—C9—C10—C11	178.15 (15)	O1—C8—N2—N1	−5.0 (2)
C9—C10—C11—C12	0.3 (3)	C9—C8—N2—N1	177.36 (13)
C10—C11—C12—C13	−1.3 (3)	C1—N1—N2—C8	167.86 (15)
C11—C12—C13—C14	−0.1 (3)	C13—C14—N3—C15	5.2 (3)
C12—C13—C14—N3	−177.36 (17)	C9—C14—N3—C15	−174.63 (17)
C12—C13—C14—C9	2.5 (3)	C16—C15—N3—C14	−63.0 (3)
C10—C9—C14—N3	176.43 (16)	C20—C15—N3—C14	120.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C9–C14 and C15–C20 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.86 (2)	2.53 (2)	3.3194 (18)	153 (2)
N2—H2N···N1ⁱ	0.86 (2)	2.34 (2)	3.0563 (18)	141 (2)
N3—H3N···O1	0.86 (2)	1.99 (2)	2.691 (2)	139 (2)
C10—H10···O1ⁱ	0.95	2.51	3.278 (2)	138
C12—H12···Cg3ⁱⁱ	0.95	2.91	3.737 (2)	146
C21—H21C···Cg2ⁱⁱⁱ	0.98	2.94	3.720 (3)	138

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

Funding information

Funding for this research was provided by: NSF–MRI program (grant No. CHE-1039027), for the purchase of the X-ray diffractometer.

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