1,4-Di-n-octyl-1,2,3,4-tetra­hydro­quinoxaline-2,3-dione

El Bourakadi, K.; El Bakri, Y.; Sebhaoui, J.; Rayni, I.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S241431461700520X

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 4| April 2017| x170520

https://doi.org/10.1107/S241431461700520X

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1,4-Di-n-octyl-1,2,3,4-tetrahydroquinoxaline-2,3-dione

Khadija El Bourakadi,^a ^* Youness El Bakri,^a Jihad Sebhaoui,^a Ibtissam Rayni,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Mohammed V University, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: elbourakadi25@gmail.com

Edited by P. C. Healy, Griffith University, Australia (Received 24 March 2017; accepted 5 April 2017; online 11 April 2017)

In the title compound, C₂₄H₃₈N₂O₂, the heterocyclic ring (r.m.s. = 0.015 Å) deviates from planarity to a greater extent than the benzene ring (r.m.s. deviation = 0.007 Å). In the crystal, the molecules pack to form polar and non-polar regions. The major intermolecular interaction appears to be complementary π-stacking between oppositely oriented tetrahydroquinoxaline units.

Keywords: crystal structure; π-stacking; quinoxaline.

CCDC reference: 1542476

Structure description

Quinoxaline derivatives are known as antagonists for the excitatory system (Fray et al., 2001 ), anticonvulsants, (De Sarro et al., 2003 ) and as antibacterial and antifungal agents (Tandon et al., 2006 ; Kotharkar & Shinde, 2006 ). As a continuation of our work in this area (Mustaphi et al., 2001 ; Ferfra et al., 2001 ), we have synthesized the new title compound and determined its crystal structure.

In the title molecule (Fig. 1), the C1–C6 ring is planar to within 0.0109 (16) Å with an r.m.s. deviation of the fitted atoms of 0.007 Å. By contrast, the maximum deviations from the N1/C7/C8/N1/C1/C2 ring are 0.0251 (16) Å (C8) and −0.0228 (15) Å (N2) with an r.m.s. deviation of 0.015 Å. As depicted in Fig. 2, the molecules pack to form polar and non-polar regions. The major intermolecular interaction appears to be complementary π-stacking between oppositely oriented tetrahydroquinoxaline units [Cg1⋯Cg2ⁱ = 3.767 (2) Å; Cg1 and Cg2 are the centroids of the N1/C7/C8/N1/C1/C2 and C1–C6 rings, respectively; symmetry code: (i) −x + $[{3\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1], which make a dihedral angle of 2.0 (1)°.

Figure 1
The title molecule with labeling scheme and 30% probability ellipsoids.

Figure 2
Packing viewed along the c-axis direction.

Synthesis and crystallization

A mixture of quinoxaline-2,3-dione (1 g, 6.17 mmol), K₂CO₃ (2.13 g, 15.42 mmol), octyl bromide(2.13 ml, 12.33 mmol) and tetra n-butylammonium bromide as a catalyst in dimethylformamide (60 ml), was stirred at room temperature for 48 h. The solution was filtered by suction and the solvent was removed under reduced pressure. The residue was chromatographed on a silica-gel column using hexane and ethyl acetate (90/10) as eluents to afford the title compound as colorless crystals upon recrystallization from ethanol solution.

Refinement

Crystal data, data collection and structure and refinement data are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₂₄H₃₈N₂O₂
M_r	386.56
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	26.407 (1), 14.3718 (5), 12.9624 (5)
β (°)	108.312 (2)
V (Å³)	4670.3 (3)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.54
Crystal size (mm)	0.25 × 0.20 × 0.07

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.78, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	17969, 4687, 2965
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.203, 1.02
No. of reflections	4687
No. of parameters	365
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.28
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014/7 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1542476

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S241431461700520X/hg4021sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S241431461700520X/hg4021Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S241431461700520X/hg4021Isup3.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: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

1,4-Di-n-octyl-1,2,3,4-tetrahydroquinoxaline-2,3-dione top

Crystal data top

C₂₄H₃₈N₂O₂	F(000) = 1696
M_r = 386.56	D_x = 1.100 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 26.407 (1) Å	Cell parameters from 8815 reflections
b = 14.3718 (5) Å	θ = 3.6–74.6°
c = 12.9624 (5) Å	µ = 0.54 mm⁻¹
β = 108.312 (2)°	T = 298 K
V = 4670.3 (3) Å³	Thick plate, colourless
Z = 8	0.25 × 0.20 × 0.07 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4687 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2965 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.065
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.9°, θ_min = 3.6°
ω scans	h = −30→33
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −17→17
T_min = 0.78, T_max = 0.96	l = −15→16
17969 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.072	Hydrogen site location: mixed
wR(F²) = 0.203	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0811P)² + 3.6894P] where P = (F_o² + 2F_c²)/3
4687 reflections	(Δ/σ)_max < 0.001
365 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.28 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. 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. Because of the significant librational motions of the last two carbon atoms of the octyl chains, it was not possible to locate the associated hydrogen atoms with confidence. These were included as riding contributions in idealized positions.

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

	x	y	z	U_iso*/U_eq
O1	0.74116 (9)	0.54364 (12)	0.59734 (18)	0.0900 (7)
O2	0.77845 (9)	0.45664 (13)	0.79053 (15)	0.0833 (6)
N1	0.70490 (8)	0.40936 (13)	0.51553 (16)	0.0557 (5)
N2	0.73887 (8)	0.32196 (12)	0.71746 (14)	0.0532 (5)
C1	0.71139 (9)	0.26985 (14)	0.62490 (18)	0.0492 (5)
C2	0.70215 (10)	0.17526 (17)	0.6314 (2)	0.0595 (6)
H2	0.7170 (10)	0.1495 (16)	0.697 (2)	0.056 (7)*
C3	0.67539 (12)	0.12529 (18)	0.5395 (2)	0.0708 (8)
H3	0.6691 (10)	0.062 (2)	0.545 (2)	0.076 (8)*
C4	0.65768 (12)	0.16928 (19)	0.4408 (3)	0.0728 (8)
H4	0.6376 (12)	0.138 (2)	0.380 (3)	0.089 (10)*
C5	0.66673 (11)	0.26283 (17)	0.4326 (2)	0.0621 (7)
H5	0.6520 (10)	0.2918 (18)	0.365 (2)	0.067 (8)*
C6	0.69430 (9)	0.31416 (15)	0.52398 (18)	0.0503 (5)
C7	0.73204 (10)	0.46110 (16)	0.6031 (2)	0.0626 (7)
C8	0.75199 (10)	0.41277 (16)	0.7119 (2)	0.0604 (6)
C9	0.69058 (11)	0.4552 (2)	0.4085 (2)	0.0644 (7)
H9A	0.7150 (11)	0.507 (2)	0.419 (2)	0.079 (8)*
H9B	0.6974 (10)	0.4120 (19)	0.356 (2)	0.070 (8)*
C10	0.63381 (11)	0.48941 (19)	0.3665 (2)	0.0619 (7)
H10A	0.6284 (10)	0.5282 (18)	0.422 (2)	0.064 (7)*
H10B	0.6084 (10)	0.4385 (19)	0.360 (2)	0.069 (7)*
C11	0.62461 (12)	0.5370 (2)	0.2581 (3)	0.0745 (8)
H11A	0.6500 (13)	0.589 (2)	0.269 (2)	0.099 (10)*
H11B	0.6350 (15)	0.492 (3)	0.203 (3)	0.121 (12)*
C12	0.56892 (13)	0.5723 (2)	0.2037 (3)	0.0769 (8)
H12A	0.5564 (13)	0.612 (2)	0.255 (3)	0.105 (11)*
H12B	0.5409 (13)	0.523 (2)	0.194 (2)	0.096 (10)*
C13	0.56333 (15)	0.6179 (3)	0.0948 (3)	0.0942 (11)
H13A	0.5897 (17)	0.668 (3)	0.112 (3)	0.136 (16)*
H13B	0.5719 (16)	0.566 (3)	0.044 (3)	0.143 (16)*
C14	0.50903 (18)	0.6512 (3)	0.0323 (3)	0.1102 (13)
H14B	0.4791 (18)	0.598 (3)	0.030 (3)	0.157 (17)*
H14A	0.4975 (10)	0.6937 (18)	0.085 (2)	0.063 (7)*
C15	0.50677 (19)	0.6956 (4)	−0.0776 (4)	0.1469 (19)
H15A	0.5305	0.7506	−0.0632	0.176*
H15B	0.5211	0.6503	−0.1190	0.176*
C16	0.4567 (2)	0.7227 (5)	−0.1415 (4)	0.177 (2)
H16A	0.4590	0.7499	−0.2092	0.266*
H16B	0.4330	0.6684	−0.1583	0.266*
H16C	0.4424	0.7690	−0.1025	0.266*
C17	0.75789 (12)	0.2801 (2)	0.8271 (2)	0.0619 (7)
H17A	0.7569 (10)	0.327 (2)	0.873 (2)	0.071 (8)*
H17B	0.7347 (11)	0.2350 (19)	0.827 (2)	0.069 (8)*
C18	0.81408 (12)	0.2432 (2)	0.8558 (2)	0.0640 (7)
H18A	0.8340 (11)	0.285 (2)	0.827 (2)	0.081 (9)*
H18B	0.8127 (10)	0.1829 (19)	0.819 (2)	0.064 (7)*
C19	0.84036 (14)	0.2334 (2)	0.9775 (2)	0.0696 (7)
H19A	0.8744 (11)	0.195 (2)	0.990 (2)	0.077 (8)*
H19B	0.8182 (12)	0.201 (2)	1.009 (2)	0.086 (10)*
C20	0.85371 (18)	0.3267 (2)	1.0348 (3)	0.0858 (9)
H20B	0.8221 (13)	0.361 (2)	1.027 (2)	0.089 (10)*
H20A	0.8800 (15)	0.362 (2)	1.013 (3)	0.113 (13)*
C21	0.88719 (16)	0.3219 (3)	1.1508 (3)	0.0897 (10)
H21B	0.8680 (13)	0.276 (2)	1.190 (3)	0.099 (10)*
H21A	0.9239 (16)	0.288 (3)	1.155 (3)	0.134 (14)*
C22	0.8982 (2)	0.4168 (3)	1.2046 (4)	0.1124 (14)
H22A	0.9188 (14)	0.453 (3)	1.168 (3)	0.102 (13)*
H22B	0.8648 (17)	0.445 (3)	1.199 (3)	0.136 (16)*
C23	0.9322 (2)	0.4163 (4)	1.3191 (4)	0.1512 (19)
H23A	0.9674	0.3896	1.3240	0.181*
H23B	0.9157	0.3762	1.3618	0.181*
C24	0.9397 (3)	0.5124 (5)	1.3667 (5)	0.233 (4)
H24A	0.9624	0.5095	1.4426	0.349*
H24B	0.9566	0.5520	1.3254	0.349*
H24C	0.9049	0.5386	1.3631	0.349*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1099 (17)	0.0429 (10)	0.1054 (16)	−0.0037 (9)	0.0169 (13)	0.0042 (9)
O2	0.1063 (16)	0.0604 (11)	0.0740 (13)	−0.0030 (10)	0.0151 (11)	−0.0195 (10)
N1	0.0601 (12)	0.0460 (10)	0.0617 (12)	0.0050 (8)	0.0200 (10)	0.0052 (9)
N2	0.0612 (12)	0.0481 (10)	0.0517 (11)	0.0075 (8)	0.0199 (10)	−0.0027 (8)
C1	0.0497 (12)	0.0458 (11)	0.0546 (13)	0.0056 (9)	0.0198 (11)	−0.0015 (10)
C2	0.0661 (16)	0.0495 (13)	0.0618 (16)	0.0061 (11)	0.0185 (13)	0.0081 (12)
C3	0.0801 (19)	0.0443 (13)	0.0819 (19)	−0.0054 (12)	0.0168 (15)	−0.0018 (13)
C4	0.081 (2)	0.0570 (15)	0.0701 (18)	−0.0004 (13)	0.0087 (16)	−0.0105 (14)
C5	0.0685 (16)	0.0571 (14)	0.0566 (15)	0.0097 (12)	0.0139 (13)	0.0004 (12)
C6	0.0515 (13)	0.0448 (11)	0.0568 (14)	0.0062 (9)	0.0199 (11)	−0.0008 (10)
C7	0.0680 (16)	0.0432 (12)	0.0752 (17)	0.0056 (11)	0.0208 (14)	−0.0004 (12)
C8	0.0656 (16)	0.0497 (13)	0.0654 (16)	0.0062 (11)	0.0200 (13)	−0.0092 (12)
C9	0.0667 (17)	0.0571 (14)	0.0695 (17)	0.0029 (12)	0.0215 (14)	0.0145 (13)
C10	0.0627 (16)	0.0545 (14)	0.0685 (17)	0.0045 (12)	0.0204 (14)	0.0072 (12)
C11	0.0706 (19)	0.0750 (18)	0.0780 (19)	0.0070 (15)	0.0235 (16)	0.0205 (15)
C12	0.0704 (19)	0.0771 (19)	0.080 (2)	0.0067 (15)	0.0189 (16)	0.0140 (16)
C13	0.083 (2)	0.109 (3)	0.083 (2)	0.014 (2)	0.0160 (19)	0.029 (2)
C14	0.098 (3)	0.127 (3)	0.098 (3)	0.022 (3)	0.021 (2)	0.026 (2)
C15	0.113 (3)	0.205 (5)	0.107 (3)	0.038 (3)	0.011 (3)	0.058 (3)
C16	0.163 (5)	0.228 (7)	0.139 (4)	0.051 (5)	0.044 (4)	0.034 (4)
C17	0.0705 (18)	0.0654 (16)	0.0525 (15)	0.0023 (13)	0.0234 (13)	−0.0026 (13)
C18	0.0739 (18)	0.0602 (15)	0.0580 (16)	0.0107 (13)	0.0210 (14)	0.0002 (13)
C19	0.080 (2)	0.0648 (16)	0.0616 (17)	0.0072 (15)	0.0191 (15)	0.0048 (13)
C20	0.099 (3)	0.076 (2)	0.074 (2)	0.0035 (19)	0.0147 (19)	−0.0045 (16)
C21	0.093 (2)	0.091 (2)	0.076 (2)	0.0020 (19)	0.0146 (19)	−0.0038 (18)
C22	0.107 (3)	0.109 (3)	0.102 (3)	0.002 (3)	0.006 (3)	−0.032 (2)
C23	0.138 (4)	0.164 (5)	0.127 (4)	0.012 (3)	0.007 (3)	−0.034 (3)
C24	0.242 (8)	0.192 (6)	0.202 (6)	0.013 (5)	−0.021 (6)	−0.111 (5)

Geometric parameters (Å, º) top

O1—C7	1.217 (3)	C14—C15	1.545 (6)
O2—C8	1.215 (3)	C14—H14B	1.10 (5)
N1—C7	1.358 (3)	C14—H14A	1.03 (3)
N1—C6	1.408 (3)	C15—C16	1.378 (6)
N1—C9	1.474 (3)	C15—H15A	0.9900
N2—C8	1.358 (3)	C15—H15B	0.9900
N2—C1	1.407 (3)	C16—H16A	0.9800
N2—C17	1.478 (3)	C16—H16B	0.9800
C1—C2	1.388 (3)	C16—H16C	0.9800
C1—C6	1.396 (3)	C17—C18	1.508 (4)
C2—C3	1.380 (4)	C17—H17A	0.91 (3)
C2—H2	0.90 (2)	C17—H17B	0.89 (3)
C3—C4	1.371 (4)	C18—C19	1.518 (4)
C3—H3	0.93 (3)	C18—H18A	0.95 (3)
C4—C5	1.376 (4)	C18—H18B	0.98 (3)
C4—H4	0.91 (3)	C19—C20	1.519 (4)
C5—C6	1.391 (3)	C19—H19A	1.03 (3)
C5—H5	0.94 (3)	C19—H19B	0.94 (3)
C7—C8	1.511 (4)	C20—C21	1.488 (5)
C9—C10	1.507 (4)	C20—H20B	0.95 (3)
C9—H9A	0.97 (3)	C20—H20A	0.97 (4)
C9—H9B	0.98 (3)	C21—C22	1.518 (5)
C10—C11	1.512 (4)	C21—H21B	1.05 (3)
C10—H10A	0.96 (3)	C21—H21A	1.07 (4)
C10—H10B	0.98 (3)	C22—C23	1.473 (6)
C11—C12	1.505 (4)	C22—H22A	0.98 (3)
C11—H11A	0.98 (3)	C22—H22B	0.96 (4)
C11—H11B	1.06 (4)	C23—C24	1.500 (7)
C12—C13	1.520 (4)	C23—H23A	0.9900
C12—H12A	1.01 (3)	C23—H23B	0.9900
C12—H12B	1.01 (3)	C24—H24A	0.9800
C13—C14	1.487 (5)	C24—H24B	0.9800
C13—H13A	0.98 (4)	C24—H24C	0.9800
C13—H13B	1.06 (4)

C7—N1—C6	122.2 (2)	C13—C14—H14A	105.3 (15)
C7—N1—C9	117.0 (2)	C15—C14—H14A	115.7 (15)
C6—N1—C9	120.6 (2)	H14B—C14—H14A	94 (3)
C8—N2—C1	122.6 (2)	C16—C15—C14	115.0 (4)
C8—N2—C17	115.3 (2)	C16—C15—H15A	108.5
C1—N2—C17	122.1 (2)	C14—C15—H15A	108.5
C2—C1—C6	119.5 (2)	C16—C15—H15B	108.5
C2—C1—N2	121.5 (2)	C14—C15—H15B	108.5
C6—C1—N2	119.0 (2)	H15A—C15—H15B	107.5
C3—C2—C1	120.6 (3)	C15—C16—H16A	109.5
C3—C2—H2	123.8 (15)	C15—C16—H16B	109.5
C1—C2—H2	115.3 (15)	H16A—C16—H16B	109.5
C4—C3—C2	119.8 (3)	C15—C16—H16C	109.5
C4—C3—H3	120.0 (17)	H16A—C16—H16C	109.5
C2—C3—H3	120.2 (17)	H16B—C16—H16C	109.5
C3—C4—C5	120.4 (3)	N2—C17—C18	113.0 (2)
C3—C4—H4	121.1 (19)	N2—C17—H17A	105.4 (17)
C5—C4—H4	118.4 (19)	C18—C17—H17A	109.1 (17)
C4—C5—C6	120.7 (3)	N2—C17—H17B	105.8 (17)
C4—C5—H5	118.4 (16)	C18—C17—H17B	111.4 (18)
C6—C5—H5	120.8 (16)	H17A—C17—H17B	112 (2)
C5—C6—C1	119.0 (2)	C17—C18—C19	112.5 (2)
C5—C6—N1	120.9 (2)	C17—C18—H18A	107.5 (17)
C1—C6—N1	120.2 (2)	C19—C18—H18A	109.9 (17)
O1—C7—N1	123.1 (2)	C17—C18—H18B	107.8 (15)
O1—C7—C8	119.2 (2)	C19—C18—H18B	111.0 (14)
N1—C7—C8	117.8 (2)	H18A—C18—H18B	108 (2)
O2—C8—N2	122.9 (2)	C18—C19—C20	112.8 (2)
O2—C8—C7	119.0 (2)	C18—C19—H19A	107.6 (15)
N2—C8—C7	118.1 (2)	C20—C19—H19A	110.4 (16)
N1—C9—C10	114.7 (2)	C18—C19—H19B	110.5 (18)
N1—C9—H9A	104.7 (17)	C20—C19—H19B	108.4 (18)
C10—C9—H9A	110.1 (16)	H19A—C19—H19B	107 (2)
N1—C9—H9B	108.5 (15)	C21—C20—C19	115.2 (3)
C10—C9—H9B	109.7 (15)	C21—C20—H20B	111.0 (19)
H9A—C9—H9B	109 (2)	C19—C20—H20B	110.3 (19)
C9—C10—C11	109.6 (2)	C21—C20—H20A	94 (2)
C9—C10—H10A	106.5 (15)	C19—C20—H20A	113 (2)
C11—C10—H10A	114.7 (15)	H20B—C20—H20A	112 (3)
C9—C10—H10B	111.3 (15)	C20—C21—C22	112.9 (3)
C11—C10—H10B	110.9 (15)	C20—C21—H21B	107.0 (18)
H10A—C10—H10B	104 (2)	C22—C21—H21B	113.2 (18)
C12—C11—C10	115.9 (3)	C20—C21—H21A	108 (2)
C12—C11—H11A	109.4 (19)	C22—C21—H21A	110 (2)
C10—C11—H11A	108.2 (19)	H21B—C21—H21A	105 (3)
C12—C11—H11B	108 (2)	C23—C22—C21	115.2 (4)
C10—C11—H11B	110 (2)	C23—C22—H22A	104 (2)
H11A—C11—H11B	104 (3)	C21—C22—H22A	108 (2)
C11—C12—C13	112.1 (3)	C23—C22—H22B	109 (3)
C11—C12—H12A	111.0 (19)	C21—C22—H22B	108 (3)
C13—C12—H12A	114.1 (19)	H22A—C22—H22B	112 (4)
C11—C12—H12B	113.0 (18)	C22—C23—C24	111.7 (5)
C13—C12—H12B	109.6 (18)	C22—C23—H23A	109.3
H12A—C12—H12B	96 (3)	C24—C23—H23A	109.3
C14—C13—C12	116.1 (3)	C22—C23—H23B	109.3
C14—C13—H13A	112 (3)	C24—C23—H23B	109.3
C12—C13—H13A	105 (2)	H23A—C23—H23B	107.9
C14—C13—H13B	104 (2)	C23—C24—H24A	109.5
C12—C13—H13B	107 (2)	C23—C24—H24B	109.5
H13A—C13—H13B	113 (3)	H24A—C24—H24B	109.5
C13—C14—C15	112.7 (4)	C23—C24—H24C	109.5
C13—C14—H14B	111 (2)	H24A—C24—H24C	109.5
C15—C14—H14B	117 (2)	H24B—C24—H24C	109.5

C8—N2—C1—C2	174.8 (2)	C17—N2—C8—O2	1.5 (4)
C17—N2—C1—C2	−2.0 (3)	C1—N2—C8—C7	5.3 (3)
C8—N2—C1—C6	−3.6 (3)	C17—N2—C8—C7	−177.7 (2)
C17—N2—C1—C6	179.6 (2)	O1—C7—C8—O2	−2.8 (4)
C6—C1—C2—C3	−1.3 (4)	N1—C7—C8—O2	176.7 (2)
N2—C1—C2—C3	−179.6 (2)	O1—C7—C8—N2	176.5 (2)
C1—C2—C3—C4	0.0 (4)	N1—C7—C8—N2	−4.0 (3)
C2—C3—C4—C5	0.4 (5)	C7—N1—C9—C10	−99.8 (3)
C3—C4—C5—C6	0.5 (4)	C6—N1—C9—C10	85.0 (3)
C4—C5—C6—C1	−1.8 (4)	N1—C9—C10—C11	178.6 (3)
C4—C5—C6—N1	178.3 (2)	C9—C10—C11—C12	178.1 (3)
C2—C1—C6—C5	2.1 (3)	C10—C11—C12—C13	−179.3 (3)
N2—C1—C6—C5	−179.5 (2)	C11—C12—C13—C14	177.3 (4)
C2—C1—C6—N1	−177.9 (2)	C12—C13—C14—C15	−179.4 (4)
N2—C1—C6—N1	0.5 (3)	C13—C14—C15—C16	176.4 (5)
C7—N1—C6—C5	−179.5 (2)	C8—N2—C17—C18	−85.7 (3)
C9—N1—C6—C5	−4.6 (3)	C1—N2—C17—C18	91.4 (3)
C7—N1—C6—C1	0.6 (3)	N2—C17—C18—C19	159.0 (2)
C9—N1—C6—C1	175.5 (2)	C17—C18—C19—C20	−70.9 (4)
C6—N1—C7—O1	−179.4 (2)	C18—C19—C20—C21	−170.6 (3)
C9—N1—C7—O1	5.5 (4)	C19—C20—C21—C22	−178.7 (4)
C6—N1—C7—C8	1.2 (3)	C20—C21—C22—C23	−178.7 (4)
C9—N1—C7—C8	−173.9 (2)	C21—C22—C23—C24	−178.3 (5)
C1—N2—C8—O2	−175.5 (2)

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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