N′-[(E)-4-Chloro­benzyl­idene]-2-(2,3-di­methyl­anilino)benzohydrazide

Jasinski, J.P.; Akkurt, M.; Mohamed, S.K.; Dunkley, E.M.; Albayati, M.R.

doi:10.1107/S2414314617011877

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 9| September 2017| x171187

https://doi.org/10.1107/S2414314617011877

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N′-[(E)-4-Chlorobenzylidene]-2-(2,3-dimethylanilino)benzohydrazide

Jerry P. Jasinski,^a Mehmet Akkurt,^b Shaaban K. Mohamed,^c,^d Evan M. Dunkley ^a and Mustafa R. Albayati ^e ^*

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

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 6 August 2017; accepted 15 August 2017; online 8 September 2017)

In the title compound, C₂₂H₂₀ClN₃O, the dihedral angle between the planes of the chlorophenyl and dimethylphenyl rings is 66.50 (9)°. These rings make dihedral angles 47.79 (8) and 69.24 (9)°, respectively, with the central benzene ring. In the crystal, molecules are linked into a three-dimensional supramolecular network by N—H⋯O, C—H⋯O hydrogen bonds and weak C—H⋯π interactions.

Keywords: crystal structure; mefenamic acid; non-steroidal anti-inflammatory drug (NSAID); hydrazones.

CCDC reference: 1569084

Structure description

Mefenamic acid (MA) is a non-steroidal anti-inflammatory drug (NSAID), which has analgesic, anti-inflammatory and antipyretic actions (Idowu et al., 2002 ). In addition, it can be indicated for the treatment of primary dysmenorrhea (Zhang & Wan, 1998 ) and periodontitis (Corry & Moran, 1998 ). The main side effects of MA include peptic ulceration and gastric bleeding, which can be attributed to the combination of local irritation produced by the direct contact of the free carboxylic group (Arun & Ashok, 2009 ; Tegeli & More, 2014 ). It has also been reported that compounds containing the hydrazide-hydrazone or imide moiety possess good analgesic and anti-inflammatory activity (Mohamed et al., 2012 ). A number of hydrazidehydrazones have been demonstrated to possess interesting antidepressant, antibacterial, antifungal, anticonvulsant, anti-inflammatory, antimalarial and antituberculosis activities (Mohamed et al., 2015a ,b ). Based on these findings and further to our previous interest in the synthesis of hydrazone NSAIDs, we report herein the synthesis and crystal structure determination of the title compound.

The title molecule (Fig. 1) is twisted with a dihedral angle of 66.50 (9)° between the chlorophenyl and dimethylphenyl rings. The chlorophenyl and dimethylphenyl rings make dihedral angles 47.79 (8) of and 69.24 (9)°, respectively, with the central benzene ring. The methyl groups of the 2,3-dimethylphenyl unit are co-planar with its bound benzene ring [C21—C19—C20—C22 = −1.9 (3)°]. The middle bridging fragment (C1/N1/N2/O1/C8) is not planar with the torsion angle N1—N2—C8—O1 = 16.3 (2)°. All bond lengths and angles are within normal ranges and are comparable with those in related structures (Zhen & Han, 2005 ; Chantrapromma et al., 2014 ; Fun et al., 2011 ; Horkaew et al., 2012 ).

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), the molecules are linked by N—H⋯O, and C—H⋯O hydrogen bonds (Table 1) into a three dimensional network. A weak C—H⋯π interaction (Table 1) is also observed.

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.84 (2)	2.01 (2)	2.8195 (18)	161 (2)
N3—H3N⋯O1	0.85 (2)	2.02 (2)	2.708 (2)	137 (2)
C16—H16⋯O1ⁱⁱ	0.95	2.59	3.518 (2)	166
C12—H12⋯Cg3ⁱⁱⁱ	0.95	2.81	3.6466 (19)	147
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) x, y, z-1.

Figure 2
A part of packing diagram for the title compound, with hydrogen bonds drawn as dashed lines.

Synthesis and crystallization

The title compound was synthesized according to our previously reported procedure (Mohamed et al., 2015b). The crystals were collected and recrystallized from ethanol to afford pure crystals suitable for X-ray analysis with m.p. = 473 − 477 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₀ClN₃O
M_r	377.86
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	171
a, b, c (Å)	15.6759 (5), 15.7743 (5), 8.0115 (3)
β (°)	100.530 (3)
V (Å³)	1947.69 (12)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	1.86
Crystal size (mm)	0.4 × 0.4 × 0.3

Data collection
Diffractometer	Agilent Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2014 )
T_min, T_max	0.833, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7282, 3703, 3188
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.614

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.04
No. of reflections	3703
No. of parameters	252
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)	0.25, −0.32
Computer programs: CrysAlis PRO (Agilent, 2014), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1569084

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617011877/xu4030sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617011877/xu4030Isup2.hkl

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'-[(E)-4-Chlorobenzylidene]-2-(2,3-dimethylanilino)benzohydrazide top

Crystal data top

C₂₂H₂₀ClN₃O	F(000) = 792
M_r = 377.86	D_x = 1.289 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 15.6759 (5) Å	Cell parameters from 2873 reflections
b = 15.7743 (5) Å	θ = 4.0–71.1°
c = 8.0115 (3) Å	µ = 1.86 mm⁻¹
β = 100.530 (3)°	T = 171 K
V = 1947.69 (12) Å³	Prism, colourless
Z = 4	0.4 × 0.4 × 0.3 mm

Data collection top

Agilent Xcalibur Eos Gemini diffractometer	3703 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	3188 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.3°, θ_min = 4.0°
ω scans	h = −11→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→19
T_min = 0.833, T_max = 1.000	l = −9→9
7282 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) + (0.0805P)² + 0.2369P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3703 reflections	Δρ_max = 0.25 e Å⁻³
252 parameters	Δρ_min = −0.32 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.

Refinement. The C-bound H atoms were placed in calculated positions and allowed to ride on their carrier atoms: aromatic C—H = 0.95 Å, with U_iso(H) = 1.2U_eq(C), C—H_methyl = 0.98 Å with U_iso(H) = 1.5U_eq(C). The H atom of the NH group was found in a difference Fourier map and refined with N—H = 0.87 (2) Å, with U_iso(H) = 1.2U_eq(N).

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

	x	y	z	U_iso*/U_eq
C1	0.70836 (10)	0.18574 (10)	0.3822 (2)	0.0263 (3)
H1	0.6838	0.1555	0.2825	0.032*
C2	0.79706 (10)	0.16644 (10)	0.4687 (2)	0.0248 (3)
C3	0.83570 (11)	0.21061 (11)	0.6143 (2)	0.0315 (4)
H3A	0.8025	0.2506	0.6640	0.038*
C4	0.92144 (11)	0.19700 (11)	0.6868 (2)	0.0337 (4)
H4	0.9470	0.2266	0.7867	0.040*
C5	0.96965 (11)	0.13950 (10)	0.6119 (2)	0.0302 (4)
C6	0.93316 (11)	0.09513 (10)	0.4677 (2)	0.0307 (4)
H6	0.9669	0.0560	0.4173	0.037*
C7	0.84679 (11)	0.10853 (10)	0.3977 (2)	0.0279 (3)
H7	0.8211	0.0776	0.2995	0.033*
C8	0.53377 (10)	0.32116 (10)	0.3908 (2)	0.0253 (3)
C9	0.46765 (10)	0.36110 (10)	0.2587 (2)	0.0267 (3)
C10	0.48285 (13)	0.36930 (12)	0.0929 (2)	0.0371 (4)
H10	0.5355	0.3481	0.0662	0.045*
C11	0.42359 (16)	0.40722 (14)	−0.0327 (2)	0.0483 (5)
H11	0.4354	0.4131	−0.1443	0.058*
C12	0.34591 (14)	0.43681 (13)	0.0065 (2)	0.0456 (5)
H12	0.3038	0.4617	−0.0801	0.055*
C13	0.32920 (12)	0.43061 (12)	0.1687 (2)	0.0368 (4)
H13	0.2755	0.4509	0.1921	0.044*
C14	0.39028 (11)	0.39477 (11)	0.3009 (2)	0.0293 (4)
C15	0.30223 (11)	0.42961 (12)	0.5171 (2)	0.0311 (4)
C16	0.29755 (13)	0.51764 (13)	0.5204 (3)	0.0414 (4)
H16	0.3419	0.5508	0.4862	0.050*
C17	0.22818 (15)	0.55678 (13)	0.5735 (3)	0.0480 (5)
H17	0.2247	0.6169	0.5764	0.058*
C18	0.16424 (14)	0.50783 (14)	0.6223 (3)	0.0452 (5)
H18	0.1161	0.5348	0.6568	0.054*
C19	0.16843 (12)	0.42067 (13)	0.6221 (2)	0.0375 (4)
C20	0.23916 (11)	0.37978 (11)	0.5699 (2)	0.0315 (4)
C21	0.09662 (17)	0.36903 (19)	0.6768 (4)	0.0660 (7)
H21A	0.0783	0.3240	0.5938	0.099*
H21B	0.0472	0.4060	0.6838	0.099*
H21C	0.1180	0.3437	0.7884	0.099*
C22	0.24639 (16)	0.28469 (13)	0.5726 (3)	0.0508 (5)
H22A	0.2962	0.2675	0.5224	0.076*
H22B	0.1933	0.2601	0.5070	0.076*
H22C	0.2544	0.2645	0.6901	0.076*
Cl1	1.07800 (3)	0.12222 (3)	0.70239 (7)	0.04846 (18)
N1	0.66402 (8)	0.24281 (9)	0.43998 (17)	0.0265 (3)
N2	0.58792 (8)	0.26525 (9)	0.33423 (18)	0.0277 (3)
H2N	0.5781 (13)	0.2445 (13)	0.236 (2)	0.033*
N3	0.37413 (10)	0.39047 (12)	0.4626 (2)	0.0417 (4)
H3N	0.4163 (13)	0.3735 (15)	0.537 (3)	0.050*
O1	0.54090 (7)	0.33759 (8)	0.54416 (14)	0.0299 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0240 (7)	0.0287 (8)	0.0257 (7)	−0.0011 (6)	0.0032 (6)	0.0006 (6)
C2	0.0233 (7)	0.0239 (7)	0.0272 (8)	−0.0004 (6)	0.0047 (6)	0.0034 (6)
C3	0.0296 (8)	0.0324 (8)	0.0321 (8)	0.0043 (7)	0.0042 (7)	−0.0058 (7)
C4	0.0316 (8)	0.0329 (9)	0.0339 (8)	0.0008 (7)	−0.0014 (7)	−0.0046 (7)
C5	0.0226 (7)	0.0262 (8)	0.0400 (9)	0.0006 (6)	0.0006 (6)	0.0064 (7)
C6	0.0304 (8)	0.0238 (7)	0.0385 (9)	0.0059 (6)	0.0079 (7)	0.0024 (7)
C7	0.0303 (8)	0.0243 (7)	0.0286 (8)	0.0004 (6)	0.0041 (6)	−0.0002 (6)
C8	0.0198 (7)	0.0287 (7)	0.0273 (8)	−0.0010 (6)	0.0038 (6)	0.0015 (6)
C9	0.0256 (8)	0.0275 (7)	0.0257 (7)	0.0010 (6)	0.0010 (6)	0.0014 (6)
C10	0.0424 (10)	0.0393 (9)	0.0299 (9)	0.0101 (8)	0.0075 (7)	0.0023 (7)
C11	0.0655 (14)	0.0534 (12)	0.0248 (9)	0.0192 (11)	0.0050 (9)	0.0050 (8)
C12	0.0550 (12)	0.0445 (11)	0.0309 (9)	0.0191 (9)	−0.0092 (8)	0.0018 (8)
C13	0.0336 (9)	0.0368 (9)	0.0366 (9)	0.0093 (7)	−0.0032 (7)	−0.0008 (7)
C14	0.0256 (8)	0.0311 (8)	0.0301 (8)	0.0014 (6)	0.0019 (6)	0.0029 (7)
C15	0.0259 (8)	0.0379 (9)	0.0285 (8)	0.0065 (7)	0.0026 (6)	0.0045 (7)
C16	0.0432 (10)	0.0367 (10)	0.0423 (10)	−0.0058 (8)	0.0026 (8)	0.0058 (8)
C17	0.0661 (14)	0.0301 (9)	0.0455 (11)	0.0111 (9)	0.0039 (10)	−0.0010 (8)
C18	0.0495 (11)	0.0475 (11)	0.0401 (10)	0.0195 (9)	0.0125 (8)	−0.0032 (8)
C19	0.0338 (9)	0.0460 (10)	0.0345 (9)	0.0040 (8)	0.0111 (7)	−0.0005 (8)
C20	0.0330 (9)	0.0322 (9)	0.0292 (8)	0.0040 (7)	0.0057 (7)	−0.0002 (6)
C21	0.0525 (14)	0.0758 (17)	0.0790 (18)	0.0007 (12)	0.0363 (13)	0.0073 (14)
C22	0.0660 (14)	0.0329 (10)	0.0581 (13)	0.0035 (9)	0.0237 (11)	0.0012 (9)
Cl1	0.0259 (2)	0.0426 (3)	0.0702 (4)	0.00625 (17)	−0.0086 (2)	−0.0052 (2)
N1	0.0202 (6)	0.0328 (7)	0.0256 (7)	0.0014 (5)	0.0017 (5)	0.0011 (5)
N2	0.0222 (6)	0.0360 (7)	0.0232 (7)	0.0039 (5)	−0.0001 (5)	−0.0011 (6)
N3	0.0281 (8)	0.0637 (11)	0.0339 (8)	0.0181 (7)	0.0075 (6)	0.0143 (7)
O1	0.0263 (6)	0.0389 (6)	0.0235 (5)	0.0050 (5)	0.0021 (4)	0.0003 (5)

Geometric parameters (Å, º) top

C1—N1	1.275 (2)	C13—C14	1.410 (2)
C1—C2	1.468 (2)	C13—H13	0.9500
C1—H1	0.9500	C14—N3	1.367 (2)
C2—C7	1.388 (2)	C15—C20	1.388 (2)
C2—C3	1.398 (2)	C15—C16	1.391 (3)
C3—C4	1.380 (2)	C15—N3	1.422 (2)
C3—H3A	0.9500	C16—C17	1.384 (3)
C4—C5	1.385 (3)	C16—H16	0.9500
C4—H4	0.9500	C17—C18	1.377 (3)
C5—C6	1.382 (3)	C17—H17	0.9500
C5—Cl1	1.7419 (16)	C18—C19	1.377 (3)
C6—C7	1.384 (2)	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.411 (2)
C7—H7	0.9500	C19—C21	1.518 (3)
C8—O1	1.241 (2)	C20—C22	1.504 (3)
C8—N2	1.358 (2)	C21—H21A	0.9800
C8—C9	1.480 (2)	C21—H21B	0.9800
C9—C10	1.398 (2)	C21—H21C	0.9800
C9—C14	1.420 (2)	C22—H22A	0.9800
C10—C11	1.375 (3)	C22—H22B	0.9800
C10—H10	0.9500	C22—H22C	0.9800
C11—C12	1.393 (3)	N1—N2	1.3772 (18)
C11—H11	0.9500	N2—H2N	0.843 (16)
C12—C13	1.375 (3)	N3—H3N	0.846 (16)
C12—H12	0.9500

N1—C1—C2	120.50 (15)	N3—C14—C9	121.42 (15)
N1—C1—H1	119.7	C13—C14—C9	117.62 (16)
C2—C1—H1	119.7	C20—C15—C16	121.10 (17)
C7—C2—C3	118.65 (15)	C20—C15—N3	119.75 (17)
C7—C2—C1	119.84 (15)	C16—C15—N3	119.13 (17)
C3—C2—C1	121.27 (15)	C17—C16—C15	119.90 (18)
C4—C3—C2	120.92 (16)	C17—C16—H16	120.0
C4—C3—H3A	119.5	C15—C16—H16	120.1
C2—C3—H3A	119.5	C18—C17—C16	119.39 (18)
C3—C4—C5	119.07 (16)	C18—C17—H17	120.3
C3—C4—H4	120.5	C16—C17—H17	120.3
C5—C4—H4	120.5	C19—C18—C17	121.49 (18)
C6—C5—C4	121.22 (15)	C19—C18—H18	119.3
C6—C5—Cl1	119.45 (13)	C17—C18—H18	119.3
C4—C5—Cl1	119.32 (14)	C18—C19—C20	119.83 (18)
C5—C6—C7	119.09 (16)	C18—C19—C21	119.84 (19)
C5—C6—H6	120.5	C20—C19—C21	120.33 (19)
C7—C6—H6	120.5	C15—C20—C19	118.26 (16)
C6—C7—C2	121.04 (15)	C15—C20—C22	120.87 (17)
C6—C7—H7	119.5	C19—C20—C22	120.86 (18)
C2—C7—H7	119.5	C19—C21—H21A	109.5
O1—C8—N2	121.16 (14)	C19—C21—H21B	109.5
O1—C8—C9	122.94 (15)	H21A—C21—H21B	109.5
N2—C8—C9	115.90 (14)	C19—C21—H21C	109.5
C10—C9—C14	119.52 (15)	H21A—C21—H21C	109.5
C10—C9—C8	120.00 (15)	H21B—C21—H21C	109.5
C14—C9—C8	120.41 (15)	C20—C22—H22A	109.5
C11—C10—C9	121.73 (18)	C20—C22—H22B	109.5
C11—C10—H10	119.1	H22A—C22—H22B	109.5
C9—C10—H10	119.1	C20—C22—H22C	109.5
C10—C11—C12	118.82 (18)	H22A—C22—H22C	109.5
C10—C11—H11	120.6	H22B—C22—H22C	109.5
C12—C11—H11	120.6	C1—N1—N2	115.25 (14)
C13—C12—C11	120.98 (17)	C8—N2—N1	119.05 (14)
C13—C12—H12	119.5	C8—N2—H2N	123.1 (14)
C11—C12—H12	119.5	N1—N2—H2N	117.8 (14)
C12—C13—C14	121.20 (17)	C14—N3—C15	124.34 (15)
C12—C13—H13	119.4	C14—N3—H3N	115.0 (18)
C14—C13—H13	119.4	C15—N3—H3N	118.9 (18)
N3—C14—C13	120.93 (16)

N1—C1—C2—C7	−175.36 (15)	C10—C9—C14—C13	4.0 (3)
N1—C1—C2—C3	−1.0 (2)	C8—C9—C14—C13	−178.89 (15)
C7—C2—C3—C4	−0.2 (3)	C20—C15—C16—C17	−1.4 (3)
C1—C2—C3—C4	−174.63 (16)	N3—C15—C16—C17	−179.80 (17)
C2—C3—C4—C5	0.9 (3)	C15—C16—C17—C18	−0.2 (3)
C3—C4—C5—C6	−0.7 (3)	C16—C17—C18—C19	1.1 (3)
C3—C4—C5—Cl1	179.80 (14)	C17—C18—C19—C20	−0.5 (3)
C4—C5—C6—C7	−0.2 (3)	C17—C18—C19—C21	179.9 (2)
Cl1—C5—C6—C7	179.30 (13)	C16—C15—C20—C19	2.0 (3)
C5—C6—C7—C2	0.9 (3)	N3—C15—C20—C19	−179.61 (16)
C3—C2—C7—C6	−0.7 (2)	C16—C15—C20—C22	−177.56 (19)
C1—C2—C7—C6	173.79 (15)	N3—C15—C20—C22	0.8 (3)
O1—C8—C9—C10	153.40 (17)	C18—C19—C20—C15	−1.1 (3)
N2—C8—C9—C10	−25.9 (2)	C21—C19—C20—C15	178.51 (19)
O1—C8—C9—C14	−23.7 (2)	C18—C19—C20—C22	178.48 (19)
N2—C8—C9—C14	157.00 (15)	C21—C19—C20—C22	−1.9 (3)
C14—C9—C10—C11	−1.8 (3)	C2—C1—N1—N2	169.64 (14)
C8—C9—C10—C11	−178.97 (19)	O1—C8—N2—N1	−16.3 (2)
C9—C10—C11—C12	−1.1 (3)	C9—C8—N2—N1	162.97 (14)
C10—C11—C12—C13	1.8 (3)	C1—N1—N2—C8	175.36 (14)
C11—C12—C13—C14	0.5 (3)	C13—C14—N3—C15	−8.1 (3)
C12—C13—C14—N3	178.55 (19)	C9—C14—N3—C15	173.89 (18)
C12—C13—C14—C9	−3.4 (3)	C20—C15—N3—C14	115.0 (2)
C10—C9—C14—N3	−177.95 (17)	C16—C15—N3—C14	−66.6 (3)
C8—C9—C14—N3	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.84 (2)	2.01 (2)	2.8195 (18)	161 (2)
N3—H3N···O1	0.85 (2)	2.02 (2)	2.708 (2)	137 (2)
C16—H16···O1ⁱⁱ	0.95	2.59	3.518 (2)	166
C12—H12···Cg3ⁱⁱⁱ	0.95	2.81	3.6466 (19)	147

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

Acknowledgements

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

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