5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one

Ouzidan, Y.; Kandri Rodi, Y.; Essassi, E.M.; El Ammari, L.; Fronczek, F.R.; Venkatraman, R.

doi:10.1107/S1600536811005654

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o669

doi:10.1107/S1600536811005654

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5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one

Younes Ouzidan,^a Youssef Kandri Rodi,^a ^* El Mokhtar Essassi,^b Lahcen El Ammari,^c Frank R. Fronczek ^d and Ramaiyer Venkatraman ^e

^aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed, Ben Abdallah, Faculté des Sciences et Techniques, Route d'Immouzzer, BP 2202 Fès, Morocco, ^bLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences, Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V-Agdal, Rabat, Morocco, ^cLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, ^dDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA, and ^eDepartment of Chemistry and Biochemistry, Jackson State University, Jackson, MS 39217, USA
^*Correspondence e-mail: kandri_rodi@yahoo.fr

(Received 17 January 2011; accepted 15 February 2011; online 19 February 2011)

In the title molecule, C₁₆H₂₃N₃O₃, the dihedral angle between the benzimidazole and nitro group planes is 5.34 (9)° and the dihedral angle between the benzimidazole and aliphatic chain mean planes is 73.23 (5)°. The C—C—C—C torsion angles (about $[\pm]$ 176°) of the nonyl group indicate an all-antiperiplanar conformation. In the crystal, adjacent molecules are linked by pairs of N—H⋯O hydrogen bonds into inversion dimers. These molecules are further connected through C—H⋯O interactions, building tapes parallel to ( $[\overline1]$ 22).

Related literature

For background to the pharmacological and biochemical properties of benzimidazolones, see: Gbadamassi et al. (1988 ); Singh et al. (2000 ); Derand et al. (2003 ); Badarau et al. (2009 ). For similar structures, see: Saber et al. (2010 ); Ouzidan et al. (2011 ).

Experimental

Crystal data

C₁₆H₂₃N₃O₃
M_r = 305.37
Triclinic, $[P \overline 1]$
a = 5.483 (1) Å
b = 10.2092 (15) Å
c = 14.746 (3) Å
α = 74.275 (9)°
β = 79.727 (6)°
γ = 83.410 (8)°
V = 779.9 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 90 K
0.35 × 0.27 × 0.22 mm

Data collection

Nonius KappaCCD diffractometer
21087 measured reflections
6349 independent reflections
5183 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.113
S = 1.03
6349 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	1.89	2.7651 (9)	170
C6—H6⋯O3ⁱⁱ	0.95	2.58	3.3139 (11)	134
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x, -y+1, -z+1.

Data collection: COLLECT (Nonius, 2000 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811005654/gk2342sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811005654/gk2342Isup2.hkl

checkCIF report

Comment top

Benzimidazoles are useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest (Gbadamassi et al., 1988). Benzimidazolone and its derivatives are also an important class of bioactive molecules in the field of drugs and pharmaceuticals (Derand et al., 2003). They found potential applications in diverse therapeutic areas including, anti-hypertensives and anti-virals (Badarau et al., 2009; Singh et al., 2000). The structural studies of benzimidazolone, linked to an isopropenyl and nonyl group respectively, have been published by Saber et al. (2010)and Ouzidan et al. (2011).

The 5-nitro-1-nonyl-1H-benzimidazol-2(3H)-one molecule structure is built up from two fused six-and five-membered rings linked to C₉H₁₉ chain as shown in Fig.1. The aliphatic chain has all-antiperiplanar (all-trans) conformation. Furthermore, the fused-ring system and the nitro group are almost planar, with a maximum deviation of 0.0414 (8) Å and 0.0250 (7) Å for C4 and N1 respectively. The dihedral angle between the two rings and nitro group planes is 5.34 (9)°. The torsion angles C1 N2 C8 C9 and C13 C14 C15 C16 are 113.66 (8)° and 177.26 (7)° respectively.

In the crystal, adjacent molecules are linked by pairs of N—H···O hydrogen bonds into inversion dimers. These molecules are further connected through C—H···O hydrogen bonds into a tape parallel to the (-1 2 2) plane, as schown in Fig. 2 and Table 1.

Related literature top

For background to the pharmacological and biochemical properties of benzimidazolones, see: Gbadamassi et al. (1988); Singh et al. (2000); Derand et al. (2003); Badarau et al. (2009). For similar structures, see: Saber et al. (2010); Ouzidan et al. (2011).

Experimental top

To 5-nitro-1H-benzoimidazol-2(3H)-one (0.2 g, 1.1 mmol), potassium carbonate (0.30 g, 2.2 mmol) and tetra-n-butylammonium bromide (0.07 g, 0.2 mmol) in DMF (15 ml) was added 1-bromononane (0.43 ml, 2.2 mmol). Stirring was continued at room temperature for 6 h. The salt was removed by filtration and the filtrate concentrated under reduced pressure. The residue was separated by chromatography on a column of silica gel with ethyl acetate/hexane (1/2) as eluent. Colorless needle-shaped crystals were isolated when the solvent was allowed to evaporate [(m.p. 392–394 K (ethanol)].

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. : Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Partial packing view of the title compound, showing tapes in the (-1 2 2) plane, built up from molecules linked through N—H···O hydrogen bonds and intermolecular C–H···O contacts (dashed lines).

5-Nitro-1-nonyl-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₆H₂₃N₃O₃	Z = 2
M_r = 305.37	F(000) = 328
Triclinic, P1	D_x = 1.300 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.483 (1) Å	Cell parameters from 5537 reflections
b = 10.2092 (15) Å	θ = 2.5–34.9°
c = 14.746 (3) Å	µ = 0.09 mm⁻¹
α = 74.275 (9)°	T = 90 K
β = 79.727 (6)°	Needle, colourless
γ = 83.410 (8)°	0.35 × 0.27 × 0.22 mm
V = 779.9 (2) Å³

Data collection top

Nonius KappaCCD diffractometer	5183 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	θ_max = 34.9°, θ_min = 2.8°
ω and ϕ scans	h = −8→8
21087 measured reflections	k = −15→16
6349 independent reflections	l = −23→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0578P)² + 0.1462P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6349 reflections	Δρ_max = 0.45 e Å⁻³
201 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (5)

Crystal data top

C₁₆H₂₃N₃O₃	γ = 83.410 (8)°
M_r = 305.37	V = 779.9 (2) Å³
Triclinic, P1	Z = 2
a = 5.483 (1) Å	Mo Kα radiation
b = 10.2092 (15) Å	µ = 0.09 mm⁻¹
c = 14.746 (3) Å	T = 90 K
α = 74.275 (9)°	0.35 × 0.27 × 0.22 mm
β = 79.727 (6)°

Data collection top

Nonius KappaCCD diffractometer	5183 reflections with I > 2σ(I)
21087 measured reflections	R_int = 0.023
6349 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.03	Δρ_max = 0.45 e Å⁻³
6349 reflections	Δρ_min = −0.28 e Å⁻³
201 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > σ(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	0.92795 (11)	1.07035 (6)	0.37556 (4)	0.01618 (12)
O2	0.40529 (12)	0.45052 (6)	0.71989 (4)	0.02109 (13)
O3	0.12666 (12)	0.41865 (6)	0.64166 (5)	0.02143 (13)
N1	0.78463 (12)	0.88673 (7)	0.50035 (5)	0.01369 (12)
H1	0.8751	0.8904	0.5431	0.016*
N2	0.61923 (12)	0.93607 (7)	0.36748 (4)	0.01292 (12)
N3	0.29292 (13)	0.48382 (7)	0.65097 (5)	0.01591 (13)
C1	0.79248 (13)	0.97452 (8)	0.41127 (5)	0.01294 (13)
C2	0.50448 (13)	0.82444 (7)	0.42883 (5)	0.01255 (13)
C3	0.61268 (13)	0.79137 (8)	0.51286 (5)	0.01240 (13)
C4	0.54726 (13)	0.68061 (8)	0.58770 (5)	0.01379 (13)
H4	0.6229	0.6565	0.6437	0.017*
C5	0.36219 (13)	0.60623 (7)	0.57568 (5)	0.01384 (13)
C6	0.24677 (14)	0.63920 (8)	0.49481 (6)	0.01500 (13)
H6	0.1193	0.5860	0.4912	0.018*
C7	0.31799 (14)	0.75013 (8)	0.41917 (5)	0.01431 (13)
H7	0.2421	0.7740	0.3632	0.017*
C8	0.56136 (14)	1.00911 (8)	0.27295 (5)	0.01453 (13)
H8A	0.6475	1.0948	0.2508	0.017*
H8B	0.3804	1.0338	0.2778	0.017*
C9	0.63787 (14)	0.92606 (8)	0.19926 (5)	0.01496 (13)
H9A	0.5714	0.9758	0.1402	0.018*
H9B	0.5589	0.8382	0.2237	0.018*
C10	0.91760 (14)	0.89612 (8)	0.17380 (5)	0.01536 (14)
H10A	0.9848	0.8397	0.2311	0.018*
H10B	1.0005	0.9829	0.1522	0.018*
C11	0.97314 (15)	0.82089 (8)	0.09493 (6)	0.01648 (14)
H11A	0.8959	0.7325	0.1186	0.020*
H11B	0.8936	0.8751	0.0400	0.020*
C12	1.24889 (15)	0.79376 (8)	0.06003 (6)	0.01714 (14)
H12A	1.3281	0.7349	0.1137	0.021*
H12B	1.3293	0.8813	0.0386	0.021*
C13	1.29159 (14)	0.72462 (8)	−0.02204 (6)	0.01650 (14)
H13A	1.2188	0.6349	0.0010	0.020*
H13B	1.2018	0.7809	−0.0735	0.020*
C14	1.56428 (15)	0.70296 (8)	−0.06374 (6)	0.01707 (14)
H14A	1.6346	0.7928	−0.0918	0.020*
H14B	1.6575	0.6522	−0.0118	0.020*
C15	1.59873 (15)	0.62433 (9)	−0.14015 (6)	0.01812 (15)
H15A	1.5350	0.5330	−0.1111	0.022*
H15B	1.4981	0.6728	−0.1903	0.022*
C16	1.86819 (17)	0.60708 (10)	−0.18635 (7)	0.02506 (18)
H16A	1.9271	0.6967	−0.2215	0.038*
H16B	1.8795	0.5492	−0.2304	0.038*
H16C	1.9712	0.5643	−0.1368	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0171 (2)	0.0163 (3)	0.0153 (2)	−0.00631 (19)	−0.00140 (19)	−0.0029 (2)
O2	0.0265 (3)	0.0195 (3)	0.0162 (3)	−0.0041 (2)	−0.0049 (2)	−0.0008 (2)
O3	0.0224 (3)	0.0188 (3)	0.0235 (3)	−0.0096 (2)	−0.0006 (2)	−0.0048 (2)
N1	0.0147 (3)	0.0147 (3)	0.0125 (3)	−0.0040 (2)	−0.0026 (2)	−0.0035 (2)
N2	0.0138 (3)	0.0137 (3)	0.0117 (3)	−0.0029 (2)	−0.0018 (2)	−0.0032 (2)
N3	0.0177 (3)	0.0143 (3)	0.0153 (3)	−0.0031 (2)	0.0006 (2)	−0.0044 (2)
C1	0.0130 (3)	0.0138 (3)	0.0126 (3)	−0.0014 (2)	−0.0010 (2)	−0.0048 (2)
C2	0.0120 (3)	0.0132 (3)	0.0126 (3)	−0.0014 (2)	−0.0005 (2)	−0.0043 (2)
C3	0.0119 (3)	0.0133 (3)	0.0130 (3)	−0.0020 (2)	−0.0009 (2)	−0.0052 (2)
C4	0.0143 (3)	0.0145 (3)	0.0128 (3)	−0.0020 (2)	−0.0011 (2)	−0.0041 (2)
C5	0.0147 (3)	0.0123 (3)	0.0141 (3)	−0.0024 (2)	0.0000 (2)	−0.0034 (2)
C6	0.0140 (3)	0.0150 (3)	0.0168 (3)	−0.0028 (2)	−0.0017 (2)	−0.0051 (3)
C7	0.0132 (3)	0.0159 (3)	0.0148 (3)	−0.0020 (2)	−0.0030 (2)	−0.0046 (2)
C8	0.0158 (3)	0.0147 (3)	0.0125 (3)	0.0003 (2)	−0.0026 (2)	−0.0028 (2)
C9	0.0157 (3)	0.0172 (3)	0.0125 (3)	−0.0017 (2)	−0.0026 (2)	−0.0043 (2)
C10	0.0163 (3)	0.0171 (3)	0.0135 (3)	−0.0011 (2)	−0.0024 (2)	−0.0053 (3)
C11	0.0173 (3)	0.0189 (3)	0.0142 (3)	−0.0006 (3)	−0.0017 (2)	−0.0065 (3)
C12	0.0179 (3)	0.0196 (4)	0.0153 (3)	−0.0003 (3)	−0.0029 (3)	−0.0071 (3)
C13	0.0168 (3)	0.0184 (3)	0.0150 (3)	−0.0001 (3)	−0.0020 (2)	−0.0063 (3)
C14	0.0173 (3)	0.0181 (3)	0.0157 (3)	−0.0004 (3)	−0.0015 (3)	−0.0053 (3)
C15	0.0200 (3)	0.0183 (4)	0.0157 (3)	0.0012 (3)	−0.0015 (3)	−0.0056 (3)
C16	0.0217 (4)	0.0302 (5)	0.0221 (4)	0.0022 (3)	0.0013 (3)	−0.0094 (3)

Geometric parameters (Å, º) top

O1—C1	1.2387 (9)	C9—H9A	0.9900
O2—N3	1.2313 (9)	C9—H9B	0.9900
O3—N3	1.2352 (9)	C10—C11	1.5297 (11)
N1—C1	1.3715 (10)	C10—H10A	0.9900
N1—C3	1.3864 (9)	C10—H10B	0.9900
N1—H1	0.8800	C11—C12	1.5268 (11)
N2—C1	1.3838 (10)	C11—H11A	0.9900
N2—C2	1.3842 (10)	C11—H11B	0.9900
N2—C8	1.4628 (10)	C12—C13	1.5303 (11)
N3—C5	1.4646 (10)	C12—H12A	0.9900
C2—C7	1.3893 (10)	C12—H12B	0.9900
C2—C3	1.4109 (10)	C13—C14	1.5272 (11)
C3—C4	1.3787 (11)	C13—H13A	0.9900
C4—C5	1.3970 (11)	C13—H13B	0.9900
C4—H4	0.9500	C14—C15	1.5263 (11)
C5—C6	1.3924 (11)	C14—H14A	0.9900
C6—C7	1.3930 (11)	C14—H14B	0.9900
C6—H6	0.9500	C15—C16	1.5246 (12)
C7—H7	0.9500	C15—H15A	0.9900
C8—C9	1.5266 (11)	C15—H15B	0.9900
C8—H8A	0.9900	C16—H16A	0.9800
C8—H8B	0.9900	C16—H16B	0.9800
C9—C10	1.5284 (11)	C16—H16C	0.9800

C1—N1—C3	109.78 (6)	C9—C10—C11	110.76 (6)
C1—N1—H1	125.1	C9—C10—H10A	109.5
C3—N1—H1	125.1	C11—C10—H10A	109.5
C1—N2—C2	109.39 (6)	C9—C10—H10B	109.5
C1—N2—C8	124.01 (6)	C11—C10—H10B	109.5
C2—N2—C8	126.52 (6)	H10A—C10—H10B	108.1
O2—N3—O3	123.41 (7)	C12—C11—C10	114.85 (6)
O2—N3—C5	118.20 (7)	C12—C11—H11A	108.6
O3—N3—C5	118.39 (7)	C10—C11—H11A	108.6
O1—C1—N1	127.21 (7)	C12—C11—H11B	108.6
O1—C1—N2	125.74 (7)	C10—C11—H11B	108.6
N1—C1—N2	107.04 (6)	H11A—C11—H11B	107.5
N2—C2—C7	131.59 (7)	C11—C12—C13	112.22 (6)
N2—C2—C3	106.99 (6)	C11—C12—H12A	109.2
C7—C2—C3	121.42 (7)	C13—C12—H12A	109.2
C4—C3—N1	131.24 (7)	C11—C12—H12B	109.2
C4—C3—C2	121.98 (7)	C13—C12—H12B	109.2
N1—C3—C2	106.77 (6)	H12A—C12—H12B	107.9
C3—C4—C5	115.49 (7)	C14—C13—C12	114.38 (7)
C3—C4—H4	122.3	C14—C13—H13A	108.7
C5—C4—H4	122.3	C12—C13—H13A	108.7
C6—C5—C4	123.69 (7)	C14—C13—H13B	108.7
C6—C5—N3	118.32 (7)	C12—C13—H13B	108.7
C4—C5—N3	117.95 (7)	H13A—C13—H13B	107.6
C5—C6—C7	120.08 (7)	C15—C14—C13	112.45 (7)
C5—C6—H6	120.0	C15—C14—H14A	109.1
C7—C6—H6	120.0	C13—C14—H14A	109.1
C2—C7—C6	117.29 (7)	C15—C14—H14B	109.1
C2—C7—H7	121.4	C13—C14—H14B	109.1
C6—C7—H7	121.4	H14A—C14—H14B	107.8
N2—C8—C9	113.04 (6)	C16—C15—C14	113.56 (7)
N2—C8—H8A	109.0	C16—C15—H15A	108.9
C9—C8—H8A	109.0	C14—C15—H15A	108.9
N2—C8—H8B	109.0	C16—C15—H15B	108.9
C9—C8—H8B	109.0	C14—C15—H15B	108.9
H8A—C8—H8B	107.8	H15A—C15—H15B	107.7
C8—C9—C10	115.31 (6)	C15—C16—H16A	109.5
C8—C9—H9A	108.4	C15—C16—H16B	109.5
C10—C9—H9A	108.4	H16A—C16—H16B	109.5
C8—C9—H9B	108.4	C15—C16—H16C	109.5
C10—C9—H9B	108.4	H16A—C16—H16C	109.5
H9A—C9—H9B	107.5	H16B—C16—H16C	109.5

C3—N1—C1—O1	−178.59 (7)	C3—C4—C5—N3	177.28 (6)
C3—N1—C1—N2	1.29 (8)	O2—N3—C5—C6	175.91 (7)
C2—N2—C1—O1	179.64 (7)	O3—N3—C5—C6	−3.41 (11)
C8—N2—C1—O1	−3.45 (12)	O2—N3—C5—C4	−1.82 (10)
C2—N2—C1—N1	−0.24 (8)	O3—N3—C5—C4	178.86 (7)
C8—N2—C1—N1	176.67 (6)	C4—C5—C6—C7	1.40 (12)
C1—N2—C2—C7	178.96 (8)	N3—C5—C6—C7	−176.19 (7)
C8—N2—C2—C7	2.15 (13)	N2—C2—C7—C6	178.47 (7)
C1—N2—C2—C3	−0.87 (8)	C3—C2—C7—C6	−1.72 (11)
C8—N2—C2—C3	−177.68 (6)	C5—C6—C7—C2	−0.33 (11)
C1—N1—C3—C4	176.91 (8)	C1—N2—C8—C9	113.65 (8)
C1—N1—C3—C2	−1.82 (8)	C2—N2—C8—C9	−69.97 (9)
N2—C2—C3—C4	−177.25 (7)	N2—C8—C9—C10	−66.44 (9)
C7—C2—C3—C4	2.90 (11)	C8—C9—C10—C11	−176.26 (6)
N2—C2—C3—N1	1.62 (8)	C9—C10—C11—C12	176.47 (7)
C7—C2—C3—N1	−178.23 (7)	C10—C11—C12—C13	−177.19 (7)
N1—C3—C4—C5	179.65 (7)	C11—C12—C13—C14	176.46 (7)
C2—C3—C4—C5	−1.79 (11)	C12—C13—C14—C15	175.71 (7)
C3—C4—C5—C6	−0.32 (11)	C13—C14—C15—C16	177.26 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.89	2.7651 (9)	170
C6—H6···O3ⁱⁱ	0.95	2.58	3.3139 (11)	134

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

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃N₃O₃
M_r	305.37
Crystal system, space group	Triclinic, P1
Temperature (K)	90
a, b, c (Å)	5.483 (1), 10.2092 (15), 14.746 (3)
α, β, γ (°)	74.275 (9), 79.727 (6), 83.410 (8)
V (Å³)	779.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.27 × 0.22

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	21087, 6349, 5183
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.805

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.113, 1.03
No. of reflections	6349
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.28

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	1.89	2.7651 (9)	170
C6—H6···O3ⁱⁱ	0.95	2.58	3.3139 (11)	134

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

References

Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339–340. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 3| March 2011| Page o669

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