(4Z)-4-[1-(2-Amino­anilino)ethyl­idene]-3-methyl-1-phenyl-4,5-di­hydro-1H-pyrazol-5-one

Samba, M.; Djerrari, B.; Minnih, M.S.; Ramli, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617002565

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170256

https://doi.org/10.1107/S2414314617002565

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(4Z)-4-[1-(2-Aminoanilino)ethylidene]-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one

Mohamed Samba,^a ^* Bahia Djerrari,^a Mohamed Said Minnih,^b Youssef Ramli,^c El Mokhtar Essassi ^a and Joel T. Mague ^d

^aLaboratoire de Chimie Organique Heterocyclique, Faculté des Sciences, Mohammed V University, Rabat, Morocco, ^bUnité de Chimie Moleculaire et Environnement, Faculté des Sciences et Techniques, Université de Sciences, de Technologie et de Medecine Nouakchott, Mauritania, ^cLaboratory of Medicinal Chemistry, Faculty of Medicine and Pharmacy, Mohammed V University, Rabat, Morocco, and ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: mohamed_samba77@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 4 February 2017; accepted 14 February 2017; online 17 February 2017)

The conformation of the title compound, C₁₈H₁₈N₄O, is partly determined by an intramolecular N—H⋯O hydrogen bond that imposes planarity on the central aminoethylidene-3-methylpyrazol-5-one segment of the molecule. In the crystal, N—H⋯O hydrogen and N—H⋯N hydrogen bonds both form centrosymmetric dimers that enclose R₂²(18) rings. These, together with C—H⋯N and π–π stacking interactions between centrosymmetrically related pyrazalone rings, stack the molecules along the b-axis direction.

Keywords: crystal structure; hydrogen bond; pyrazolone; π-stacking.

CCDC reference: 1532587

Structure description

Pyrazole derivatives are known to possess a broad spectrum of biological activities, acting as cannabinoid receptor antagonists (Lan et al., 1999 ), antibacterial (Tanitame et al., 2004 ), anti-inflammatory and antimicrobial agents (Bekhit & Abdel-Aziem, 2004 ). In a continuation of our research using acetoacetyl pyrazole as starting material in the synthesis of several heterocyclic systems with potent pharmacological properties (Djerrari et al., 2001 ,2003 ), we report in this work the crystal structure of the title pyrazolone derivative.

The conformation of the title molecule is partially determined by an intramolecular N3—H3⋯O1 hydrogen bond (Table 1, Figs. 1 and 2). This ensures the planarity of the central C13/N3/C12(C11)[N1,N2,C1(C10)C2,C3(O1)] section of the molecule, r.m.s. deviation 0.0403 Å. The dihedral angle between the mean planes of the N1/N2/C1–C3 and C4–C9 rings is 21.31 (4)° while that between the former ring and the C13—C18 ring is 62.60 (5)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.955 (18)	1.863 (18)	2.6965 (14)	144.3 (15)
N4—H4A⋯N2ⁱ	0.92 (2)	2.47 (2)	3.2542 (17)	144.1 (16)
N4—H4B⋯O1ⁱⁱ	0.93 (2)	2.14 (2)	3.0090 (16)	153.3 (17)
C9—H9⋯N4ⁱ	1.008 (17)	2.567 (17)	3.571 (2)	173.7 (13)
C11—H11C⋯N1ⁱⁱⁱ	0.98 (2)	2.68 (2)	3.5669 (19)	152.0 (16)
C18—H18⋯N2ⁱⁱⁱ	0.997 (17)	2.439 (17)	3.3984 (18)	161.2 (13)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+2, -z+1.

Figure 1
The title molecule with the labelling scheme and 50% probability displacement ellipsoids. The intramolecular hydrogen bond is shown as a dashed line.

Figure 2
Detail of the intra- and intermolecular molecular interactions (dashed lines: N—H⋯O, blue; N—H⋯N, purple; C—H⋯O; black; π–π stacking, orange). For symmetry codes, see Table 1

In the crystal, the molecules form centrosymmetric dimers through pairwise N4—H4B⋯O1ⁱⁱ hydrogen bonds, Table 1. N1—H4A⋯N2ⁱ hydrogen bonds also form inversion dimers with both sets of dimers forming R₂²(18) ring motifs. The dimers stack along the b-axis direction aided by C9—H9⋯N4ⁱ, C11—H11C⋯N1ⁱⁱⁱ and C18—H18⋯N2ⁱⁱⁱ hydrogen bonds and offset π–π-stacking interactions [Cg1⋯Cg1^iv = 3.758 (1) Å; symmetry code: (iv) 1 − x, 1 − y, 1 − z] between pairs of centrosymmetrically related pyrazolone rings (Table 1, Figs. 2 and 3). The individual stacks show only normal van der Waals contacts between them.

Figure 3
Crystal packing, viewed along the a axis (the colour codes for the hydrogen bonds are given in Fig. 2

Synthesis and crystallization

To a solution of acetoacetyl pyrazole (0.001 mol) in 40 ml of ethanol was added o-phenylenediamine (0.002 mol). The reaction mixture was refluxed for 2 h. After cooling, the solvent was removed under reduced pressure. The residue obtained was recrystallized from ethanol to afford colourless block-like crystals of the title compound (m.p. 485–487 K, yield: 80%).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄O
M_r	306.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	8.6575 (2), 7.1749 (1), 25.3062 (5)
β (°)	93.782 (1)
V (Å³)	1568.51 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.67
Crystal size (mm)	0.19 × 0.05 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.87, 0.97
No. of measured, independent and observed [I > 2σ(I)] reflections	11756, 3032, 2596
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.04
No. of reflections	3032
No. of parameters	281
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.18
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1532587

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002565/sj4087sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002565/sj4087Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617002565/sj4087Isup3.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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(4Z)-4-[1-(2-Aminoanilino)ethylidene]-3-methyl-1-phenyl-4,5-dihydro-1H-pyrazol-5-one top

Crystal data top

C₁₈H₁₈N₄O	F(000) = 648
M_r = 306.36	D_x = 1.297 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 8.6575 (2) Å	Cell parameters from 8108 reflections
b = 7.1749 (1) Å	θ = 5.1–72.4°
c = 25.3062 (5) Å	µ = 0.67 mm⁻¹
β = 93.782 (1)°	T = 150 K
V = 1568.51 (5) Å³	Column, colourless
Z = 4	0.19 × 0.05 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3032 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2596 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.035
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.4°, θ_min = 5.1°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
T_min = 0.87, T_max = 0.97	l = −31→30
11756 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	All H-atom parameters refined
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0455P)² + 0.4468P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.29 e Å⁻³
3032 reflections	Δρ_min = −0.18 e Å⁻³
281 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0050 (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	0.23306 (10)	0.69400 (14)	0.45467 (4)	0.0305 (2)
N1	0.48083 (12)	0.71074 (15)	0.42251 (4)	0.0248 (2)
N2	0.63327 (12)	0.73552 (16)	0.44323 (4)	0.0270 (3)
N3	0.25320 (13)	0.75094 (16)	0.56022 (4)	0.0276 (3)
C1	0.62652 (14)	0.75905 (17)	0.49448 (5)	0.0248 (3)
C2	0.47020 (14)	0.74833 (17)	0.50980 (5)	0.0234 (3)
C3	0.37694 (14)	0.71531 (17)	0.46141 (5)	0.0241 (3)
H3	0.203 (2)	0.721 (2)	0.5265 (7)	0.044 (5)*
C4	0.45262 (15)	0.68737 (17)	0.36708 (5)	0.0258 (3)
H4A	0.132 (2)	0.447 (3)	0.5721 (8)	0.051 (5)*
H4B	−0.032 (2)	0.404 (3)	0.5913 (8)	0.057 (6)*
N4	0.05992 (15)	0.47138 (18)	0.59596 (6)	0.0405 (3)
C5	0.30760 (17)	0.7256 (2)	0.34286 (5)	0.0316 (3)
H5	0.221 (2)	0.771 (2)	0.3632 (7)	0.040 (4)*
C6	0.28126 (19)	0.6947 (2)	0.28880 (6)	0.0406 (4)
H6	0.179 (2)	0.722 (3)	0.2718 (7)	0.047 (5)*
C7	0.3984 (2)	0.6291 (3)	0.25907 (6)	0.0451 (4)
H7	0.379 (2)	0.604 (3)	0.2209 (8)	0.057 (5)*
C8	0.5442 (2)	0.5994 (2)	0.28307 (6)	0.0417 (4)
H8	0.631 (2)	0.552 (3)	0.2629 (7)	0.052 (5)*
C9	0.57317 (17)	0.6281 (2)	0.33724 (6)	0.0332 (3)
H9	0.680 (2)	0.607 (2)	0.3542 (6)	0.037 (4)*
C10	0.77427 (16)	0.7937 (2)	0.52661 (6)	0.0338 (3)
H10A	0.769 (2)	0.910 (3)	0.5479 (7)	0.045 (5)*
H10B	0.795 (2)	0.693 (3)	0.5525 (8)	0.054 (5)*
H10C	0.862 (2)	0.799 (3)	0.5015 (8)	0.049 (5)*
C11	0.50207 (16)	0.8055 (2)	0.60909 (5)	0.0294 (3)
H11A	0.450 (2)	0.766 (3)	0.6404 (8)	0.056 (5)*
H11B	0.601 (2)	0.738 (3)	0.6094 (8)	0.054 (5)*
H11C	0.527 (2)	0.938 (3)	0.6128 (8)	0.063 (6)*
C12	0.40601 (15)	0.76834 (17)	0.55887 (5)	0.0242 (3)
C13	0.16041 (15)	0.78645 (19)	0.60397 (5)	0.0266 (3)
C14	0.05963 (14)	0.64562 (19)	0.61874 (5)	0.0284 (3)
C15	−0.04064 (16)	0.6879 (2)	0.65830 (6)	0.0341 (3)
H15	−0.113 (2)	0.588 (3)	0.6692 (7)	0.045 (5)*
C16	−0.04014 (16)	0.8615 (2)	0.68174 (6)	0.0366 (3)
H16	−0.112 (2)	0.889 (3)	0.7101 (7)	0.046 (5)*
C17	0.06066 (17)	0.9995 (2)	0.66678 (6)	0.0367 (3)
H17	0.062 (2)	1.130 (3)	0.6819 (7)	0.050 (5)*
C18	0.15980 (16)	0.9615 (2)	0.62736 (5)	0.0325 (3)
H18	0.2297 (18)	1.060 (2)	0.6150 (6)	0.037 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0219 (4)	0.0418 (6)	0.0276 (5)	−0.0053 (4)	0.0004 (3)	−0.0017 (4)
N1	0.0222 (5)	0.0283 (6)	0.0236 (5)	−0.0018 (4)	0.0002 (4)	0.0002 (4)
N2	0.0223 (5)	0.0285 (6)	0.0301 (6)	−0.0015 (4)	0.0006 (4)	0.0002 (5)
N3	0.0266 (6)	0.0329 (6)	0.0232 (5)	−0.0051 (5)	0.0022 (4)	−0.0021 (5)
C1	0.0243 (6)	0.0210 (6)	0.0289 (6)	−0.0004 (5)	−0.0003 (5)	0.0008 (5)
C2	0.0244 (6)	0.0215 (6)	0.0243 (6)	−0.0010 (5)	−0.0002 (5)	0.0003 (5)
C3	0.0244 (6)	0.0226 (6)	0.0253 (6)	−0.0015 (5)	0.0016 (5)	0.0010 (5)
C4	0.0325 (7)	0.0213 (6)	0.0235 (6)	−0.0048 (5)	0.0025 (5)	0.0009 (5)
N4	0.0266 (6)	0.0327 (7)	0.0626 (9)	−0.0049 (5)	0.0061 (6)	−0.0072 (6)
C5	0.0326 (7)	0.0354 (8)	0.0267 (6)	−0.0071 (6)	0.0006 (5)	0.0046 (6)
C6	0.0432 (8)	0.0506 (9)	0.0274 (7)	−0.0149 (7)	−0.0036 (6)	0.0073 (7)
C7	0.0627 (10)	0.0494 (10)	0.0233 (7)	−0.0182 (8)	0.0034 (7)	0.0001 (7)
C8	0.0562 (10)	0.0385 (9)	0.0321 (7)	−0.0047 (7)	0.0146 (7)	−0.0037 (7)
C9	0.0386 (8)	0.0292 (7)	0.0323 (7)	0.0000 (6)	0.0067 (6)	−0.0004 (6)
C10	0.0249 (7)	0.0394 (8)	0.0363 (7)	−0.0009 (6)	−0.0041 (6)	−0.0039 (7)
C11	0.0323 (7)	0.0300 (7)	0.0254 (6)	−0.0018 (6)	−0.0021 (5)	−0.0013 (6)
C12	0.0275 (6)	0.0193 (6)	0.0257 (6)	−0.0019 (5)	0.0010 (5)	0.0017 (5)
C13	0.0243 (6)	0.0328 (7)	0.0229 (6)	−0.0019 (5)	0.0014 (5)	0.0021 (5)
C14	0.0218 (6)	0.0303 (7)	0.0324 (7)	−0.0008 (5)	−0.0032 (5)	0.0045 (6)
C15	0.0246 (6)	0.0406 (8)	0.0375 (7)	−0.0016 (6)	0.0038 (5)	0.0093 (6)
C16	0.0305 (7)	0.0493 (9)	0.0309 (7)	0.0033 (6)	0.0075 (6)	0.0031 (7)
C17	0.0374 (8)	0.0386 (8)	0.0345 (7)	0.0002 (6)	0.0060 (6)	−0.0040 (7)
C18	0.0337 (7)	0.0328 (7)	0.0316 (7)	−0.0057 (6)	0.0061 (6)	−0.0009 (6)

Geometric parameters (Å, º) top

O1—C3	1.2554 (15)	C7—H7	0.985 (19)
N1—C3	1.3769 (16)	C8—C9	1.392 (2)
N1—N2	1.3990 (15)	C8—H8	0.999 (19)
N1—C4	1.4178 (16)	C9—H9	1.008 (17)
N2—C1	1.3132 (17)	C10—H10A	0.99 (2)
N3—C12	1.3316 (17)	C10—H10B	0.98 (2)
N3—C13	1.4330 (16)	C10—H10C	1.021 (19)
N3—H3	0.955 (18)	C11—C12	1.4962 (18)
C1—C2	1.4342 (17)	C11—H11A	0.98 (2)
C1—C10	1.4906 (18)	C11—H11B	0.99 (2)
C2—C12	1.4007 (17)	C11—H11C	0.98 (2)
C2—C3	1.4413 (17)	C13—C18	1.388 (2)
C4—C5	1.3878 (19)	C13—C14	1.4017 (18)
C4—C9	1.3945 (19)	C14—C15	1.4007 (19)
N4—C14	1.3768 (19)	C15—C16	1.380 (2)
N4—H4A	0.92 (2)	C15—H15	1.000 (18)
N4—H4B	0.93 (2)	C16—C17	1.389 (2)
C5—C6	1.390 (2)	C16—H16	1.002 (18)
C5—H5	0.991 (17)	C17—C18	1.385 (2)
C6—C7	1.385 (2)	C17—H17	1.01 (2)
C6—H6	0.976 (19)	C18—H18	0.997 (17)
C7—C8	1.380 (2)

C3—N1—N2	111.94 (10)	C8—C9—H9	119.9 (9)
C3—N1—C4	129.21 (11)	C4—C9—H9	121.1 (9)
N2—N1—C4	118.84 (10)	C1—C10—H10A	111.7 (10)
C1—N2—N1	106.51 (10)	C1—C10—H10B	110.7 (12)
C12—N3—C13	127.72 (11)	H10A—C10—H10B	105.5 (15)
C12—N3—H3	112.9 (11)	C1—C10—H10C	108.2 (11)
C13—N3—H3	119.2 (11)	H10A—C10—H10C	111.5 (14)
N2—C1—C2	111.37 (11)	H10B—C10—H10C	109.2 (15)
N2—C1—C10	117.88 (12)	C12—C11—H11A	112.0 (12)
C2—C1—C10	130.74 (12)	C12—C11—H11B	110.7 (11)
C12—C2—C1	132.12 (12)	H11A—C11—H11B	107.4 (16)
C12—C2—C3	122.50 (11)	C12—C11—H11C	111.3 (12)
C1—C2—C3	105.35 (11)	H11A—C11—H11C	108.4 (16)
O1—C3—N1	126.09 (11)	H11B—C11—H11C	106.8 (16)
O1—C3—C2	129.10 (11)	N3—C12—C2	117.79 (11)
N1—C3—C2	104.81 (10)	N3—C12—C11	119.49 (11)
C5—C4—C9	120.57 (13)	C2—C12—C11	122.72 (12)
C5—C4—N1	120.36 (12)	C18—C13—C14	121.23 (12)
C9—C4—N1	119.06 (12)	C18—C13—N3	120.55 (12)
C14—N4—H4A	118.0 (13)	C14—C13—N3	117.93 (12)
C14—N4—H4B	120.0 (12)	N4—C14—C15	120.93 (13)
H4A—N4—H4B	115.7 (17)	N4—C14—C13	121.64 (13)
C4—C5—C6	119.22 (14)	C15—C14—C13	117.42 (13)
C4—C5—H5	121.8 (10)	C16—C15—C14	121.21 (13)
C6—C5—H5	118.9 (10)	C16—C15—H15	120.8 (10)
C7—C6—C5	120.70 (15)	C14—C15—H15	118.0 (10)
C7—C6—H6	120.2 (11)	C15—C16—C17	120.71 (13)
C5—C6—H6	119.1 (11)	C15—C16—H16	120.0 (11)
C8—C7—C6	119.64 (14)	C17—C16—H16	119.3 (11)
C8—C7—H7	119.9 (11)	C18—C17—C16	119.10 (14)
C6—C7—H7	120.5 (11)	C18—C17—H17	117.6 (10)
C7—C8—C9	120.70 (14)	C16—C17—H17	123.2 (10)
C7—C8—H8	121.8 (11)	C17—C18—C13	120.32 (13)
C9—C8—H8	117.5 (11)	C17—C18—H18	120.3 (9)
C8—C9—C4	119.05 (14)	C13—C18—H18	119.4 (9)

C3—N1—N2—C1	−1.13 (14)	C6—C7—C8—C9	2.4 (3)
C4—N1—N2—C1	178.18 (11)	C7—C8—C9—C4	0.1 (2)
N1—N2—C1—C2	0.78 (14)	C5—C4—C9—C8	−3.0 (2)
N1—N2—C1—C10	−178.48 (12)	N1—C4—C9—C8	177.95 (13)
N2—C1—C2—C12	−178.39 (13)	C13—N3—C12—C2	−172.18 (12)
C10—C1—C2—C12	0.7 (2)	C13—N3—C12—C11	8.6 (2)
N2—C1—C2—C3	−0.19 (14)	C1—C2—C12—N3	179.71 (13)
C10—C1—C2—C3	178.94 (14)	C3—C2—C12—N3	1.77 (18)
N2—N1—C3—O1	−178.75 (12)	C1—C2—C12—C11	−1.1 (2)
C4—N1—C3—O1	2.0 (2)	C3—C2—C12—C11	−179.04 (12)
N2—N1—C3—C2	0.99 (14)	C12—N3—C13—C18	58.78 (19)
C4—N1—C3—C2	−178.23 (12)	C12—N3—C13—C14	−127.44 (14)
C12—C2—C3—O1	−2.3 (2)	C18—C13—C14—N4	−179.68 (13)
C1—C2—C3—O1	179.25 (13)	N3—C13—C14—N4	6.59 (19)
C12—C2—C3—N1	177.93 (11)	C18—C13—C14—C15	−0.54 (19)
C1—C2—C3—N1	−0.48 (13)	N3—C13—C14—C15	−174.28 (12)
C3—N1—C4—C5	21.3 (2)	N4—C14—C15—C16	179.20 (13)
N2—N1—C4—C5	−157.89 (12)	C13—C14—C15—C16	0.1 (2)
C3—N1—C4—C9	−159.63 (13)	C14—C15—C16—C17	−0.2 (2)
N2—N1—C4—C9	21.19 (17)	C15—C16—C17—C18	0.8 (2)
C9—C4—C5—C6	3.4 (2)	C16—C17—C18—C13	−1.3 (2)
N1—C4—C5—C6	−177.52 (13)	C14—C13—C18—C17	1.2 (2)
C4—C5—C6—C7	−1.0 (2)	N3—C13—C18—C17	174.77 (13)
C5—C6—C7—C8	−1.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.955 (18)	1.863 (18)	2.6965 (14)	144.3 (15)
N4—H4A···N2ⁱ	0.92 (2)	2.47 (2)	3.2542 (17)	144.1 (16)
N4—H4B···O1ⁱⁱ	0.93 (2)	2.14 (2)	3.0090 (16)	153.3 (17)
C9—H9···N4ⁱ	1.008 (17)	2.567 (17)	3.571 (2)	173.7 (13)
C11—H11C···N1ⁱⁱⁱ	0.98 (2)	2.68 (2)	3.5669 (19)	152.0 (16)
C18—H18···N2ⁱⁱⁱ	0.997 (17)	2.439 (17)	3.3984 (18)	161.2 (13)

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

Acknowledgements

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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