(3S,4S)-4-Phenyl-1,5-bis­(prop-2-en-1-yl)-3-(prop-2-en-1-yl­oxy)-2,3,4,5-tetra­hydro-1H-1,5-benzo­diazepin-2-one

Rida, M.; El Bakri, Y.; Sebbar, N.K.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616011755

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 7| July 2016| x161175

https://doi.org/10.1107/S2414314616011755

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(3S,4S)-4-Phenyl-1,5-bis(prop-2-en-1-yl)-3-(prop-2-en-1-yloxy)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one

Mohammed Rida,^a ^* Youness El Bakri,^a Nada Kheira Sebbar,^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: rida.m.b@hotmail.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 1 July 2016; accepted 19 July 2016; online 29 July 2016)

In the title compound, C₂₄H₂₆N₂O₂, the dihedral angle between the benzene rings is 45.69 (7)°. In the crystal, the molecules form helical supramolecular chains running parallel to the b axis via weak C—H⋯O hydrogen bonds.

Keywords: crystal structure; benzodiazepine derivative; hydrogen bond.

CCDC reference: 1494818

Structure description

1,5-Benzodiazepine derivatives have been used as therapeutics for viral infection and cardiovascular disorder (Jacob et al., 2011 ; Maleki et al., 2014 ). They are active against peptide hormones (Werner et al., 1990 ) and potassium blockers (Claremon et al., 1996 ). They are also employed as intermediates for the synthesis of several heterocyclic compounds (Minnih et al., 2014 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound.

In the title molecule (Fig. 1), the dihedral angle between the C1–C6 and C10–C15 rings is 45.69 (7)°. Analysis of the conformation of the seven-membered ring yielded puckering parameters Q(2) = 1.034 (2) Å, φ(2) = 227.0 (1)°, Q(3) = 0.174 (2) Å and φ(3) = 1.3 (6)°. In the crystal, the molecules form supramolecular helical chains parallel to the b axis through C22—H22A⋯O1(−x + 1, y + $[{1\over 2}]$ , −z) hydrogen bonds (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C22—H22A⋯O1ⁱ	0.99	2.41	3.378 (2)	165
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z]$ .

Figure 1
The title molecule with labeling scheme and 50% probability ellipsoids.

Figure 2
Packing viewed along the a axis with C—H⋯O hydrogen bonds shown as dashed lines.

Synthesis and crystallization

To a solution of 3-hydroxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one (1 g, 3.5 mmol) in DMF (20 ml) were added allyl bromide (0.5 g. 10.5 mmol), potassium carbonate (1 g, 7.4 mmol) and a catalytic quantity of tetra-n-butyl ammonium bromide. The mixture was stirred at room temperature for 24 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol solution to afford the compound as colorless crystals.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₆N₂O₂
M_r	374.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	9.6138 (2), 8.8891 (2), 11.7292 (3)
β (°)	97.127 (1)
V (Å³)	994.61 (4)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.63
Crystal size (mm)	0.21 × 0.15 × 0.14

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.84, 0.90
No. of measured, independent and observed [I > 2σ(I)] reflections	9888, 3881, 3744
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.624

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.05
No. of reflections	3881
No. of parameters	254
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.21
Absolute structure	Flack x determined using 1608 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.00 (8)
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: 1494818

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616011755/xu4010sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616011755/xu4010Isup2.hkl

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).

(3S,4S)-4-Phenyl-1,5-bis(prop-2-en-1-yl)-3-(prop-2-en-1-yloxy)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one top

Crystal data top

C₂₄H₂₆N₂O₂	F(000) = 400
M_r = 374.47	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 9.6138 (2) Å	Cell parameters from 9162 reflections
b = 8.8891 (2) Å	θ = 3.8–74.3°
c = 11.7292 (3) Å	µ = 0.63 mm⁻¹
β = 97.127 (1)°	T = 150 K
V = 994.61 (4) Å³	Block, colourless
Z = 2	0.21 × 0.15 × 0.14 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3881 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3744 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.3°, θ_min = 3.8°
ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −11→11
T_min = 0.84, T_max = 0.90	l = −14→14
9888 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.030	w = 1/[σ²(F_o²) + (0.0347P)² + 0.1749P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.075	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.18 e Å⁻³
3881 reflections	Δρ_min = −0.21 e Å⁻³
254 parameters	Extinction correction: SHELXL2014 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0076 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack x determined using 1608 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.00 (8)

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 1.00 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.36677 (15)	0.28288 (17)	0.02270 (11)	0.0310 (3)
O2	0.64430 (14)	0.29097 (15)	0.10026 (11)	0.0274 (3)
N1	0.30144 (16)	0.32889 (18)	0.19803 (13)	0.0256 (3)
N2	0.45776 (15)	0.59426 (16)	0.22157 (12)	0.0216 (3)
C1	0.40506 (18)	0.5341 (2)	0.31988 (15)	0.0223 (4)
C2	0.4206 (2)	0.6060 (2)	0.42694 (15)	0.0261 (4)
H2	0.4703	0.6984	0.4363	0.031*
C3	0.3642 (2)	0.5435 (2)	0.51948 (16)	0.0302 (4)
H3	0.3751	0.5938	0.5915	0.036*
C4	0.2924 (2)	0.4087 (2)	0.50753 (17)	0.0305 (4)
H4	0.2543	0.3662	0.5712	0.037*
C5	0.2763 (2)	0.3357 (2)	0.40224 (16)	0.0283 (4)
H5	0.2285	0.2421	0.3943	0.034*
C6	0.32954 (19)	0.3986 (2)	0.30810 (16)	0.0239 (4)
C7	0.39812 (19)	0.31974 (19)	0.12316 (15)	0.0241 (4)
C8	0.55078 (19)	0.3467 (2)	0.17397 (14)	0.0225 (4)
H8	0.5695	0.2965	0.2506	0.027*
C9	0.58168 (18)	0.51561 (19)	0.18692 (14)	0.0204 (3)
H9	0.5942	0.5537	0.1086	0.025*
C10	0.71810 (18)	0.5486 (2)	0.26366 (15)	0.0231 (4)
C11	0.8169 (2)	0.6427 (2)	0.22330 (17)	0.0289 (4)
H11	0.7991	0.6838	0.1481	0.035*
C12	0.9414 (2)	0.6774 (3)	0.2916 (2)	0.0380 (5)
H12	1.0070	0.7434	0.2635	0.046*
C13	0.9702 (2)	0.6164 (3)	0.4004 (2)	0.0387 (5)
H13	1.0559	0.6390	0.4467	0.046*
C14	0.8730 (2)	0.5220 (3)	0.44140 (18)	0.0345 (5)
H14	0.8926	0.4792	0.5159	0.041*
C15	0.7470 (2)	0.4894 (2)	0.37439 (16)	0.0285 (4)
H15	0.6802	0.4264	0.4041	0.034*
C16	0.1552 (2)	0.2936 (3)	0.15412 (18)	0.0337 (5)
H16A	0.1036	0.2701	0.2199	0.040*
H16B	0.1536	0.2025	0.1054	0.040*
C17	0.0813 (2)	0.4166 (3)	0.0863 (3)	0.0510 (7)
H17	0.1021	0.5168	0.1109	0.061*
C18	−0.0070 (4)	0.3989 (4)	−0.0016 (4)	0.0751 (10)
H18A	−0.0306	0.3004	−0.0290	0.090*
H18B	−0.0498	0.4840	−0.0404	0.090*
C19	0.6504 (2)	0.1307 (2)	0.09502 (18)	0.0312 (4)
H19A	0.6713	0.1006	0.0177	0.037*
H19B	0.5572	0.0893	0.1055	0.037*
C20	0.7576 (2)	0.0632 (2)	0.18291 (18)	0.0332 (4)
H20	0.7602	−0.0435	0.1873	0.040*
C21	0.8487 (2)	0.1365 (3)	0.25474 (19)	0.0368 (5)
H21A	0.8503	0.2434	0.2538	0.044*
H21B	0.9131	0.0828	0.3078	0.044*
C22	0.4695 (2)	0.75892 (19)	0.21535 (16)	0.0253 (4)
H22A	0.5147	0.7867	0.1469	0.030*
H22B	0.5295	0.7961	0.2843	0.030*
C23	0.3291 (2)	0.8316 (2)	0.20827 (17)	0.0316 (4)
H23	0.2597	0.7985	0.1488	0.038*
C24	0.2929 (3)	0.9369 (3)	0.2767 (2)	0.0405 (5)
H24A	0.3589	0.9734	0.3373	0.049*
H24B	0.2006	0.9769	0.2657	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0383 (8)	0.0314 (7)	0.0217 (6)	0.0001 (6)	−0.0022 (5)	−0.0053 (5)
O2	0.0341 (7)	0.0220 (6)	0.0272 (6)	0.0019 (5)	0.0080 (5)	−0.0026 (5)
N1	0.0256 (8)	0.0280 (8)	0.0224 (7)	−0.0060 (6)	0.0001 (6)	−0.0007 (6)
N2	0.0243 (7)	0.0201 (7)	0.0205 (7)	0.0002 (6)	0.0029 (5)	0.0004 (6)
C1	0.0214 (8)	0.0247 (8)	0.0205 (8)	0.0013 (7)	0.0017 (6)	0.0014 (7)
C2	0.0273 (9)	0.0274 (10)	0.0231 (9)	0.0005 (7)	0.0008 (7)	−0.0016 (7)
C3	0.0335 (10)	0.0356 (11)	0.0214 (9)	0.0044 (8)	0.0030 (7)	−0.0020 (8)
C4	0.0330 (10)	0.0345 (10)	0.0249 (9)	0.0054 (8)	0.0069 (7)	0.0067 (8)
C5	0.0296 (10)	0.0275 (9)	0.0279 (9)	0.0014 (8)	0.0048 (7)	0.0051 (8)
C6	0.0236 (8)	0.0255 (9)	0.0223 (9)	−0.0002 (7)	0.0016 (6)	0.0010 (7)
C7	0.0296 (9)	0.0187 (8)	0.0232 (8)	−0.0003 (7)	0.0004 (7)	−0.0006 (7)
C8	0.0276 (9)	0.0208 (8)	0.0190 (8)	0.0004 (7)	0.0022 (6)	−0.0008 (6)
C9	0.0238 (8)	0.0196 (8)	0.0178 (8)	0.0006 (7)	0.0028 (6)	0.0002 (6)
C10	0.0241 (9)	0.0213 (8)	0.0235 (8)	0.0031 (7)	0.0014 (6)	−0.0024 (7)
C11	0.0268 (9)	0.0300 (10)	0.0300 (10)	−0.0010 (8)	0.0036 (7)	−0.0009 (8)
C12	0.0261 (10)	0.0431 (12)	0.0446 (12)	−0.0044 (9)	0.0035 (9)	−0.0022 (10)
C13	0.0274 (10)	0.0430 (12)	0.0426 (12)	0.0030 (9)	−0.0083 (8)	−0.0104 (10)
C14	0.0374 (11)	0.0343 (10)	0.0291 (10)	0.0075 (9)	−0.0066 (8)	−0.0032 (8)
C15	0.0322 (10)	0.0272 (10)	0.0247 (9)	0.0025 (8)	−0.0016 (8)	−0.0001 (7)
C16	0.0285 (10)	0.0393 (11)	0.0317 (9)	−0.0131 (9)	−0.0026 (8)	0.0041 (9)
C17	0.0320 (12)	0.0336 (12)	0.083 (2)	−0.0002 (10)	−0.0099 (12)	0.0005 (12)
C18	0.0630 (18)	0.0597 (19)	0.092 (2)	0.0049 (16)	−0.0326 (17)	0.0235 (17)
C19	0.0375 (11)	0.0224 (9)	0.0334 (10)	0.0036 (8)	0.0030 (8)	−0.0060 (7)
C20	0.0363 (10)	0.0280 (10)	0.0366 (11)	0.0059 (8)	0.0096 (8)	0.0040 (8)
C21	0.0321 (10)	0.0410 (12)	0.0378 (11)	0.0059 (9)	0.0063 (8)	0.0041 (9)
C22	0.0301 (9)	0.0188 (8)	0.0267 (9)	−0.0014 (7)	0.0022 (7)	0.0000 (7)
C23	0.0324 (10)	0.0271 (10)	0.0340 (10)	0.0037 (8)	−0.0014 (8)	0.0005 (8)
C24	0.0416 (12)	0.0348 (12)	0.0447 (13)	0.0094 (9)	0.0044 (10)	−0.0033 (9)

Geometric parameters (Å, º) top

O1—C7	1.224 (2)	C12—C13	1.382 (3)
O2—C8	1.412 (2)	C12—H12	0.9500
O2—C19	1.427 (2)	C13—C14	1.386 (3)
N1—C7	1.358 (2)	C13—H13	0.9500
N1—C6	1.427 (2)	C14—C15	1.390 (3)
N1—C16	1.470 (2)	C14—H14	0.9500
N2—C1	1.420 (2)	C15—H15	0.9500
N2—C22	1.471 (2)	C16—C17	1.480 (3)
N2—C9	1.481 (2)	C16—H16A	0.9900
C1—C2	1.400 (3)	C16—H16B	0.9900
C1—C6	1.404 (3)	C17—C18	1.262 (4)
C2—C3	1.388 (3)	C17—H17	0.9500
C2—H2	0.9500	C18—H18A	0.9500
C3—C4	1.381 (3)	C18—H18B	0.9500
C3—H3	0.9500	C19—C20	1.491 (3)
C4—C5	1.387 (3)	C19—H19A	0.9900
C4—H4	0.9500	C19—H19B	0.9900
C5—C6	1.391 (3)	C20—C21	1.311 (3)
C5—H5	0.9500	C20—H20	0.9500
C7—C8	1.533 (2)	C21—H21A	0.9500
C8—C9	1.534 (2)	C21—H21B	0.9500
C8—H8	1.0000	C22—C23	1.490 (3)
C9—C10	1.524 (2)	C22—H22A	0.9900
C9—H9	1.0000	C22—H22B	0.9900
C10—C11	1.392 (3)	C23—C24	1.308 (3)
C10—C15	1.397 (3)	C23—H23	0.9500
C11—C12	1.390 (3)	C24—H24A	0.9500
C11—H11	0.9500	C24—H24B	0.9500

C8—O2—C19	114.15 (15)	C13—C12—H12	119.8
C7—N1—C6	122.88 (15)	C11—C12—H12	119.8
C7—N1—C16	117.54 (15)	C12—C13—C14	119.42 (19)
C6—N1—C16	118.35 (16)	C12—C13—H13	120.3
C1—N2—C22	116.90 (15)	C14—C13—H13	120.3
C1—N2—C9	115.16 (14)	C13—C14—C15	120.5 (2)
C22—N2—C9	112.75 (14)	C13—C14—H14	119.7
C2—C1—C6	118.43 (16)	C15—C14—H14	119.7
C2—C1—N2	123.16 (17)	C14—C15—C10	120.37 (19)
C6—C1—N2	118.37 (16)	C14—C15—H15	119.8
C3—C2—C1	120.67 (18)	C10—C15—H15	119.8
C3—C2—H2	119.7	N1—C16—C17	113.90 (18)
C1—C2—H2	119.7	N1—C16—H16A	108.8
C4—C3—C2	120.42 (18)	C17—C16—H16A	108.8
C4—C3—H3	119.8	N1—C16—H16B	108.8
C2—C3—H3	119.8	C17—C16—H16B	108.8
C3—C4—C5	119.72 (19)	H16A—C16—H16B	107.7
C3—C4—H4	120.1	C18—C17—C16	125.2 (3)
C5—C4—H4	120.1	C18—C17—H17	117.4
C4—C5—C6	120.49 (19)	C16—C17—H17	117.4
C4—C5—H5	119.8	C17—C18—H18A	120.0
C6—C5—H5	119.8	C17—C18—H18B	120.0
C5—C6—C1	120.23 (17)	H18A—C18—H18B	120.0
C5—C6—N1	119.76 (17)	O2—C19—C20	113.60 (17)
C1—C6—N1	119.94 (16)	O2—C19—H19A	108.8
O1—C7—N1	122.14 (17)	C20—C19—H19A	108.8
O1—C7—C8	121.71 (17)	O2—C19—H19B	108.8
N1—C7—C8	116.00 (15)	C20—C19—H19B	108.8
O2—C8—C7	111.01 (14)	H19A—C19—H19B	107.7
O2—C8—C9	105.90 (14)	C21—C20—C19	126.4 (2)
C7—C8—C9	110.85 (14)	C21—C20—H20	116.8
O2—C8—H8	109.7	C19—C20—H20	116.8
C7—C8—H8	109.7	C20—C21—H21A	120.0
C9—C8—H8	109.7	C20—C21—H21B	120.0
N2—C9—C10	114.18 (14)	H21A—C21—H21B	120.0
N2—C9—C8	109.67 (14)	N2—C22—C23	111.07 (16)
C10—C9—C8	112.88 (14)	N2—C22—H22A	109.4
N2—C9—H9	106.5	C23—C22—H22A	109.4
C10—C9—H9	106.5	N2—C22—H22B	109.4
C8—C9—H9	106.5	C23—C22—H22B	109.4
C11—C10—C15	118.51 (17)	H22A—C22—H22B	108.0
C11—C10—C9	119.24 (16)	C24—C23—C22	125.8 (2)
C15—C10—C9	122.24 (16)	C24—C23—H23	117.1
C12—C11—C10	120.82 (19)	C22—C23—H23	117.1
C12—C11—H11	119.6	C23—C24—H24A	120.0
C10—C11—H11	119.6	C23—C24—H24B	120.0
C13—C12—C11	120.3 (2)	H24A—C24—H24B	120.0

C22—N2—C1—C2	−28.3 (2)	C1—N2—C9—C10	−75.02 (19)
C9—N2—C1—C2	107.57 (19)	C22—N2—C9—C10	62.63 (19)
C22—N2—C1—C6	149.46 (16)	C1—N2—C9—C8	52.80 (19)
C9—N2—C1—C6	−74.7 (2)	C22—N2—C9—C8	−169.56 (14)
C6—C1—C2—C3	0.8 (3)	O2—C8—C9—N2	157.45 (13)
N2—C1—C2—C3	178.56 (16)	C7—C8—C9—N2	36.95 (18)
C1—C2—C3—C4	0.4 (3)	O2—C8—C9—C10	−74.02 (17)
C2—C3—C4—C5	−0.2 (3)	C7—C8—C9—C10	165.48 (14)
C3—C4—C5—C6	−1.2 (3)	N2—C9—C10—C11	−105.72 (18)
C4—C5—C6—C1	2.5 (3)	C8—C9—C10—C11	128.12 (18)
C4—C5—C6—N1	−174.51 (17)	N2—C9—C10—C15	73.3 (2)
C2—C1—C6—C5	−2.2 (3)	C8—C9—C10—C15	−52.8 (2)
N2—C1—C6—C5	179.92 (16)	C15—C10—C11—C12	−0.2 (3)
C2—C1—C6—N1	174.72 (16)	C9—C10—C11—C12	178.87 (18)
N2—C1—C6—N1	−3.1 (2)	C10—C11—C12—C13	1.2 (3)
C7—N1—C6—C5	−141.28 (18)	C11—C12—C13—C14	−0.9 (3)
C16—N1—C6—C5	51.7 (2)	C12—C13—C14—C15	−0.4 (3)
C7—N1—C6—C1	41.7 (3)	C13—C14—C15—C10	1.5 (3)
C16—N1—C6—C1	−125.30 (19)	C11—C10—C15—C14	−1.2 (3)
C6—N1—C7—O1	−167.56 (17)	C9—C10—C15—C14	179.80 (18)
C16—N1—C7—O1	−0.4 (3)	C7—N1—C16—C17	−77.9 (3)
C6—N1—C7—C8	16.9 (2)	C6—N1—C16—C17	89.8 (2)
C16—N1—C7—C8	−175.97 (16)	N1—C16—C17—C18	143.0 (3)
C19—O2—C8—C7	−70.99 (19)	C8—O2—C19—C20	−89.5 (2)
C19—O2—C8—C9	168.62 (14)	O2—C19—C20—C21	−5.3 (3)
O1—C7—C8—O2	−13.5 (2)	C1—N2—C22—C23	−63.9 (2)
N1—C7—C8—O2	162.12 (15)	C9—N2—C22—C23	159.25 (15)
O1—C7—C8—C9	103.95 (19)	N2—C22—C23—C24	125.9 (2)
N1—C7—C8—C9	−80.48 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C22—H22A···O1ⁱ	0.99	2.41	3.378 (2)	165

Symmetry code: (i) −x+1, y+1/2, −z.

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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