(4E)-1-Decyl-4-(2-oxo­propyl­idene)-2,3,4,5-tetra­hydro-1H-1,5-benzodiazepin-2-one

Sebhaoui, J.; Zang Ondo, C.M.; El Bakri, Y.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616011743

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 7| July 2016| x161174

https://doi.org/10.1107/S2414314616011743

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(4E)-1-Decyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Jihad Sebhaoui,^a ^* Cherryl Mirabelle Zang Ondo,^a Youness El Bakri,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aHeterocyclic Organic Chemistry Laboratory URAC 21, Faculty of Sciences, Mohammed V University in Rabat, Av. Ibn Battouta, BP 1014 Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: sebhaoui.jihad@gmail.com

Edited by S. Bernès, Benemérita Universidad Autónoma de Puebla, México (Received 18 June 2016; accepted 19 July 2016; online 22 July 2016)

The title compound, C₂₂H₃₂N₂O₂, forms bilayers with the n-decyl chains in extended conformation oriented towards the interior of the bilayer structure. Weak C—H⋯O interactions help to stabilize the exterior surfaces. The conformation of the seven-membered ring has been analysed.

Keywords: crystal structure; benzodiazepine; bilayer.

CCDC references: 1494817; 1494817

Structure description

1,5-Benzodiazepine derivatives constitute an important class of nitrogen-containing heterocycles and possess interesting activities as anticonvulsant (Ben-Cherif et al., 2010 ), antimicrobial (Wang et al., 2015 ), and anti-inflammatory (Ha et al., 2010 ) agents. They have also been used as intermediates for the synthesis of benzimidazoles (El Azzaoui et al., 1999 ) and quinoxalines (Doumbia et al., 2008 ).

In the crystal, the title compound adopts a U-shaped conformation (Fig. 1). A puckering analysis of the conformation of the seven-membered ring yielded the parameters q₂ = 0.888 (1) Å, φ₂ = 32.74 (8)°, q₃ = 0.203 (1) Å and φ₃ = 127.5 (4)°. An intramolecular N2—H2A⋯O2 hydrogen bond (Table 1) occurs.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.887 (16)	1.904 (16)	2.6459 (14)	140.0 (14)
C5—H5⋯O2ⁱ	0.93	2.54	3.3123 (17)	140
Symmetry code: (i) x+1, y-1, z.

Figure 1
The title molecule with 30% probability ellipsoids for non-H atoms. The dashed line represents an intramolecular hydrogen bond (Table 1

, entry 1).

In the crystal, the molecules pack to form bilayers with the n-decyl chains extended to fill the interior, and with the substituted benzodiazepine units on the surfaces (Fig. 2). Weak C5—H5⋯O2ⁱ contacts [symmetry code (i): x + 1, y − 1, z] help to stabilize the hydrophilic portion (Table 1 and Fig. 2).

Figure 2
Packing structure viewed along the a axis, with C—H⋯O interactions shown as dashed lines. For clarity only the H atoms involved in these interactions are included.

Synthesis and crystallization

To a solution of (4E)-2-oxopropylidene-1,5-benzodiazepin-2-one (0.01 mol, 2.16 g) in N,N-dimethylformamide (60 ml), was added K₂CO₃ (0.02 mol, 2.76 g), 1-bromodecane (0.02 mol, 4.42 g) and tetra-n-butylammonium bromide (0.001 mol, 0.321 g). The reaction mixture was stirred at room temperature for 48 h. The solution was filtered and the solvent was removed under reduced pressure. The obtained residue was chromatographed on a silica-gel column using a mixture of hexane and ethyl acetate (80/20) as eluent, to afford the title compound as colourless crystals.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₃₂N₂O₂
M_r	356.49
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.4132 (14), 8.4870 (14), 16.670 (3)
α, β, γ (°)	83.560 (2), 85.919 (2), 62.599 (2)
V (Å³)	1049.8 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.44 × 0.32 × 0.26

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.85, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	20426, 5575, 3821
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.136, 1.04
No. of reflections	5575
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.15
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC references: 1494817; 1494817

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616011743/bh4008sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616011743/bh4008Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616011743/bh4008Isup4.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314616011743/bh4008Isup4.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).

(4E)-1-Decyl-4-(2-oxopropylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top

Crystal data top

C₂₂H₃₂N₂O₂	Z = 2
M_r = 356.49	F(000) = 388
Triclinic, P1	D_x = 1.128 Mg m⁻³
a = 8.4132 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.4870 (14) Å	Cell parameters from 7410 reflections
c = 16.670 (3) Å	θ = 2.5–28.9°
α = 83.560 (2)°	µ = 0.07 mm⁻¹
β = 85.919 (2)°	T = 296 K
γ = 62.599 (2)°	Block, colourless
V = 1049.8 (3) Å³	0.44 × 0.32 × 0.26 mm

Data collection top

Bruker SMART APEX CCD diffractometer	5575 independent reflections
Radiation source: fine-focus sealed tube	3821 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.2°, θ_min = 2.5°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→11
T_min = 0.85, T_max = 0.98	l = −22→22
20426 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)] = 0.047	Hydrogen site location: mixed
wR(F²) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0569P)² + 0.119P] where P = (F_o² + 2F_c²)/3
5575 reflections	(Δ/σ)_max = 0.001
241 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, collected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 5 sec/frame.

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

	x	y	z	U_iso*/U_eq
O1	0.47356 (13)	0.07555 (12)	0.87693 (7)	0.0643 (3)
O2	0.11670 (14)	0.84072 (12)	0.87720 (7)	0.0745 (3)
N1	0.65022 (13)	0.19922 (12)	0.82244 (6)	0.0450 (2)
N2	0.43528 (14)	0.56271 (13)	0.86512 (6)	0.0466 (3)
H2A	0.360 (2)	0.678 (2)	0.8561 (10)	0.074 (5)*
C1	0.61644 (16)	0.49845 (15)	0.84118 (7)	0.0430 (3)
C2	0.68986 (19)	0.61726 (17)	0.83285 (8)	0.0528 (3)
H2	0.6181	0.7360	0.8420	0.063*
C3	0.8672 (2)	0.5606 (2)	0.81126 (9)	0.0641 (4)
H3	0.9141	0.6415	0.8043	0.077*
C4	0.9758 (2)	0.3830 (2)	0.79987 (10)	0.0686 (4)
H4	1.0970	0.3432	0.7877	0.082*
C5	0.90426 (18)	0.26497 (18)	0.80653 (9)	0.0576 (3)
H5	0.9781	0.1460	0.7985	0.069*
C6	0.72332 (16)	0.32080 (15)	0.82512 (7)	0.0440 (3)
C7	0.53781 (16)	0.17720 (14)	0.88058 (8)	0.0448 (3)
C8	0.49415 (15)	0.29106 (14)	0.95032 (7)	0.0429 (3)
H8A	0.4383	0.2477	0.9942	0.052*
H8B	0.6035	0.2837	0.9699	0.052*
C9	0.36916 (15)	0.48169 (14)	0.92314 (7)	0.0410 (3)
C10	0.20044 (16)	0.56744 (15)	0.95487 (8)	0.0457 (3)
H10	0.1610	0.5038	0.9931	0.055*
C11	0.08004 (17)	0.75103 (16)	0.93245 (9)	0.0530 (3)
C12	−0.09418 (18)	0.83550 (19)	0.97834 (11)	0.0696 (4)
H12A	−0.0899	0.7611	1.0268	0.104*
H12B	−0.1898	0.8492	0.9455	0.104*
H12C	−0.1145	0.9503	0.9921	0.104*
C13	0.69323 (19)	0.09919 (17)	0.75086 (8)	0.0561 (3)
H13A	0.6405	0.0180	0.7577	0.067*
H13B	0.8221	0.0286	0.7460	0.067*
C14	0.62465 (19)	0.22126 (19)	0.67381 (8)	0.0580 (3)
H14A	0.6848	0.2958	0.6653	0.070*
H14B	0.6569	0.1486	0.6287	0.070*
C15	0.42421 (19)	0.34017 (19)	0.67379 (8)	0.0561 (3)
H15A	0.3926	0.4197	0.7162	0.067*
H15B	0.3635	0.2667	0.6860	0.067*
C16	0.3583 (2)	0.4507 (2)	0.59375 (8)	0.0614 (4)
H16A	0.4224	0.5209	0.5812	0.074*
H16B	0.3887	0.3703	0.5518	0.074*
C17	0.1596 (2)	0.5751 (2)	0.59099 (9)	0.0618 (4)
H17A	0.1287	0.6593	0.6313	0.074*
H17B	0.0943	0.5064	0.6047	0.074*
C18	0.1012 (2)	0.6778 (2)	0.50848 (9)	0.0656 (4)
H18A	0.1697	0.7432	0.4946	0.079*
H18B	0.1316	0.5925	0.4687	0.079*
C19	−0.0946 (2)	0.8067 (2)	0.50190 (9)	0.0663 (4)
H19A	−0.1258	0.8926	0.5414	0.080*
H19B	−0.1639	0.7418	0.5151	0.080*
C20	−0.1467 (2)	0.9068 (2)	0.41840 (10)	0.0711 (4)
H20A	−0.0756	0.9696	0.4051	0.085*
H20B	−0.1159	0.8203	0.3792	0.085*
C21	−0.3395 (3)	1.0373 (2)	0.40996 (12)	0.0848 (5)
H21A	−0.3708	1.1237	0.4492	0.102*
H21B	−0.4110	0.9746	0.4227	0.102*
C22	−0.3878 (3)	1.1358 (3)	0.32680 (14)	0.1133 (8)
H22A	−0.5132	1.2178	0.3262	0.170*
H22B	−0.3615	1.0519	0.2876	0.170*
H22C	−0.3194	1.2003	0.3139	0.170*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0662 (6)	0.0505 (5)	0.0877 (7)	−0.0352 (5)	0.0045 (5)	−0.0153 (5)
O2	0.0675 (7)	0.0420 (5)	0.0939 (8)	−0.0118 (5)	−0.0011 (6)	0.0115 (5)
N1	0.0496 (6)	0.0347 (5)	0.0484 (6)	−0.0169 (4)	−0.0028 (4)	−0.0047 (4)
N2	0.0485 (6)	0.0308 (5)	0.0531 (6)	−0.0127 (4)	−0.0031 (5)	0.0018 (4)
C1	0.0498 (7)	0.0377 (5)	0.0405 (6)	−0.0195 (5)	−0.0069 (5)	0.0020 (5)
C2	0.0699 (9)	0.0460 (6)	0.0484 (7)	−0.0322 (6)	−0.0057 (6)	0.0019 (5)
C3	0.0759 (10)	0.0689 (9)	0.0639 (9)	−0.0489 (8)	−0.0032 (7)	0.0037 (7)
C4	0.0558 (9)	0.0781 (10)	0.0751 (10)	−0.0359 (8)	0.0017 (7)	0.0036 (8)
C5	0.0497 (8)	0.0514 (7)	0.0646 (8)	−0.0187 (6)	0.0018 (6)	0.0002 (6)
C6	0.0473 (7)	0.0388 (6)	0.0441 (6)	−0.0185 (5)	−0.0046 (5)	0.0010 (5)
C7	0.0414 (6)	0.0314 (5)	0.0568 (7)	−0.0124 (5)	−0.0083 (5)	0.0001 (5)
C8	0.0425 (6)	0.0357 (5)	0.0464 (6)	−0.0150 (5)	−0.0063 (5)	0.0031 (5)
C9	0.0455 (6)	0.0333 (5)	0.0435 (6)	−0.0166 (5)	−0.0090 (5)	−0.0019 (4)
C10	0.0425 (6)	0.0368 (5)	0.0556 (7)	−0.0158 (5)	−0.0066 (5)	−0.0018 (5)
C11	0.0469 (7)	0.0394 (6)	0.0688 (9)	−0.0151 (6)	−0.0122 (6)	−0.0043 (6)
C12	0.0465 (8)	0.0482 (7)	0.1026 (12)	−0.0105 (6)	−0.0050 (8)	−0.0099 (8)
C13	0.0605 (8)	0.0414 (6)	0.0596 (8)	−0.0157 (6)	−0.0004 (6)	−0.0132 (6)
C14	0.0638 (9)	0.0600 (8)	0.0493 (7)	−0.0262 (7)	0.0052 (6)	−0.0144 (6)
C15	0.0617 (8)	0.0586 (8)	0.0466 (7)	−0.0262 (7)	−0.0004 (6)	−0.0057 (6)
C16	0.0710 (9)	0.0645 (8)	0.0481 (7)	−0.0306 (8)	−0.0023 (6)	−0.0034 (6)
C17	0.0704 (9)	0.0626 (8)	0.0512 (8)	−0.0294 (8)	−0.0069 (7)	−0.0011 (6)
C18	0.0774 (10)	0.0632 (8)	0.0546 (8)	−0.0309 (8)	−0.0082 (7)	0.0008 (7)
C19	0.0772 (10)	0.0621 (8)	0.0581 (9)	−0.0304 (8)	−0.0100 (7)	−0.0001 (7)
C20	0.0874 (12)	0.0642 (9)	0.0642 (9)	−0.0366 (9)	−0.0170 (8)	0.0040 (7)
C21	0.0953 (13)	0.0717 (10)	0.0833 (12)	−0.0334 (10)	−0.0272 (10)	0.0032 (9)
C22	0.149 (2)	0.0893 (13)	0.1018 (16)	−0.0534 (14)	−0.0625 (14)	0.0264 (12)

Geometric parameters (Å, º) top

O1—C7	1.2190 (14)	C13—H13A	0.9700
O2—C11	1.2415 (16)	C13—H13B	0.9700
N1—C7	1.3640 (16)	C14—C15	1.515 (2)
N1—C6	1.4295 (15)	C14—H14A	0.9700
N1—C13	1.4692 (16)	C14—H14B	0.9700
N2—C9	1.3579 (15)	C15—C16	1.5210 (19)
N2—C1	1.4060 (16)	C15—H15A	0.9700
N2—H2A	0.887 (16)	C15—H15B	0.9700
C1—C2	1.3955 (16)	C16—C17	1.512 (2)
C1—C6	1.4007 (16)	C16—H16A	0.9700
C2—C3	1.374 (2)	C16—H16B	0.9700
C2—H2	0.9300	C17—C18	1.525 (2)
C3—C4	1.384 (2)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.377 (2)	C18—C19	1.504 (2)
C4—H4	0.9300	C18—H18A	0.9700
C5—C6	1.3927 (18)	C18—H18B	0.9700
C5—H5	0.9300	C19—C20	1.526 (2)
C7—C8	1.5115 (17)	C19—H19A	0.9700
C8—C9	1.5054 (15)	C19—H19B	0.9700
C8—H8A	0.9700	C20—C21	1.490 (2)
C8—H8B	0.9700	C20—H20A	0.9700
C9—C10	1.3612 (17)	C20—H20B	0.9700
C10—C11	1.4367 (17)	C21—C22	1.514 (3)
C10—H10	0.9300	C21—H21A	0.9700
C11—C12	1.498 (2)	C21—H21B	0.9700
C12—H12A	0.9600	C22—H22A	0.9600
C12—H12B	0.9600	C22—H22B	0.9600
C12—H12C	0.9600	C22—H22C	0.9600
C13—C14	1.5208 (19)

C7—N1—C6	123.72 (10)	C15—C14—C13	114.50 (11)
C7—N1—C13	118.75 (10)	C15—C14—H14A	108.6
C6—N1—C13	117.46 (10)	C13—C14—H14A	108.6
C9—N2—C1	125.52 (10)	C15—C14—H14B	108.6
C9—N2—H2A	111.0 (10)	C13—C14—H14B	108.6
C1—N2—H2A	120.2 (10)	H14A—C14—H14B	107.6
C2—C1—C6	119.63 (12)	C14—C15—C16	113.14 (12)
C2—C1—N2	118.29 (11)	C14—C15—H15A	109.0
C6—C1—N2	122.07 (10)	C16—C15—H15A	109.0
C3—C2—C1	120.68 (13)	C14—C15—H15B	109.0
C3—C2—H2	119.7	C16—C15—H15B	109.0
C1—C2—H2	119.7	H15A—C15—H15B	107.8
C2—C3—C4	119.84 (13)	C17—C16—C15	115.36 (12)
C2—C3—H3	120.1	C17—C16—H16A	108.4
C4—C3—H3	120.1	C15—C16—H16A	108.4
C5—C4—C3	120.01 (14)	C17—C16—H16B	108.4
C5—C4—H4	120.0	C15—C16—H16B	108.4
C3—C4—H4	120.0	H16A—C16—H16B	107.5
C4—C5—C6	121.13 (13)	C16—C17—C18	112.79 (12)
C4—C5—H5	119.4	C16—C17—H17A	109.0
C6—C5—H5	119.4	C18—C17—H17A	109.0
C5—C6—C1	118.53 (11)	C16—C17—H17B	109.0
C5—C6—N1	119.33 (11)	C18—C17—H17B	109.0
C1—C6—N1	122.03 (11)	H17A—C17—H17B	107.8
O1—C7—N1	123.17 (12)	C19—C18—C17	115.60 (13)
O1—C7—C8	121.50 (12)	C19—C18—H18A	108.4
N1—C7—C8	115.32 (10)	C17—C18—H18A	108.4
C9—C8—C7	109.74 (9)	C19—C18—H18B	108.4
C9—C8—H8A	109.7	C17—C18—H18B	108.4
C7—C8—H8A	109.7	H18A—C18—H18B	107.4
C9—C8—H8B	109.7	C18—C19—C20	113.76 (14)
C7—C8—H8B	109.7	C18—C19—H19A	108.8
H8A—C8—H8B	108.2	C20—C19—H19A	108.8
N2—C9—C10	122.13 (10)	C18—C19—H19B	108.8
N2—C9—C8	115.85 (10)	C20—C19—H19B	108.8
C10—C9—C8	122.02 (10)	H19A—C19—H19B	107.7
C9—C10—C11	123.47 (12)	C21—C20—C19	115.22 (15)
C9—C10—H10	118.3	C21—C20—H20A	108.5
C11—C10—H10	118.3	C19—C20—H20A	108.5
O2—C11—C10	122.16 (12)	C21—C20—H20B	108.5
O2—C11—C12	119.60 (12)	C19—C20—H20B	108.5
C10—C11—C12	118.24 (13)	H20A—C20—H20B	107.5
C11—C12—H12A	109.5	C20—C21—C22	114.29 (19)
C11—C12—H12B	109.5	C20—C21—H21A	108.7
H12A—C12—H12B	109.5	C22—C21—H21A	108.7
C11—C12—H12C	109.5	C20—C21—H21B	108.7
H12A—C12—H12C	109.5	C22—C21—H21B	108.7
H12B—C12—H12C	109.5	H21A—C21—H21B	107.6
N1—C13—C14	112.14 (10)	C21—C22—H22A	109.5
N1—C13—H13A	109.2	C21—C22—H22B	109.5
C14—C13—H13A	109.2	H22A—C22—H22B	109.5
N1—C13—H13B	109.2	C21—C22—H22C	109.5
C14—C13—H13B	109.2	H22A—C22—H22C	109.5
H13A—C13—H13B	107.9	H22B—C22—H22C	109.5

C9—N2—C1—C2	−133.51 (13)	O1—C7—C8—C9	−106.01 (13)
C9—N2—C1—C6	46.96 (17)	N1—C7—C8—C9	72.89 (13)
C6—C1—C2—C3	−1.84 (19)	C1—N2—C9—C10	166.11 (11)
N2—C1—C2—C3	178.62 (12)	C1—N2—C9—C8	−13.82 (17)
C1—C2—C3—C4	−1.9 (2)	C7—C8—C9—N2	−63.37 (13)
C2—C3—C4—C5	3.0 (2)	C7—C8—C9—C10	116.70 (12)
C3—C4—C5—C6	−0.4 (2)	N2—C9—C10—C11	−2.25 (19)
C4—C5—C6—C1	−3.3 (2)	C8—C9—C10—C11	177.68 (11)
C4—C5—C6—N1	172.92 (13)	C9—C10—C11—O2	6.2 (2)
C2—C1—C6—C5	4.37 (18)	C9—C10—C11—C12	−173.27 (12)
N2—C1—C6—C5	−176.11 (11)	C7—N1—C13—C14	115.76 (13)
C2—C1—C6—N1	−171.75 (11)	C6—N1—C13—C14	−61.51 (15)
N2—C1—C6—N1	7.77 (18)	N1—C13—C14—C15	−58.53 (16)
C7—N1—C6—C5	135.27 (13)	C13—C14—C15—C16	−175.86 (12)
C13—N1—C6—C5	−47.61 (15)	C14—C15—C16—C17	−178.65 (12)
C7—N1—C6—C1	−48.64 (16)	C15—C16—C17—C18	−178.22 (13)
C13—N1—C6—C1	128.48 (12)	C16—C17—C18—C19	−178.91 (13)
C6—N1—C7—O1	178.57 (11)	C17—C18—C19—C20	179.79 (13)
C13—N1—C7—O1	1.49 (17)	C18—C19—C20—C21	−179.32 (14)
C6—N1—C7—C8	−0.31 (16)	C19—C20—C21—C22	179.61 (15)
C13—N1—C7—C8	−177.39 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.887 (16)	1.904 (16)	2.6459 (14)	140.0 (14)
C5—H5···O2ⁱ	0.93	2.54	3.3123 (17)	140

Symmetry code: (i) x+1, y−1, z.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

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