1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one

Belaziz, D.; Kandri Rodi, Y.; Ouazzani Chahdi, F.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812041189

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3069

doi:10.1107/S1600536812041189

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1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one

Dounia Belaziz,^a ^* Youssef Kandri Rodi,^a Fouad Ouazzani Chahdi,^a El Mokhtar Essassi,^b,^c Mohamed Saadi ^d and Lahcen El Ammari ^d

^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 URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, ^cInstitute of Nanmaterials and Nanotechnology, MASCIR, Rabat, Morocco, and ^dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: d_belaziz@yahoo.fr

(Received 15 September 2012; accepted 1 October 2012; online 6 October 2012)

In the title compound, C₁₉H₃₀N₂O, the fused ring system is essentially planar, the maximum deviation from the mean plane being 0.013 (2) Å for the N atom bearing the dodecyl chain. The 1-dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle of 82.9 (2)°between planes through the fused ring system and the first three C atoms of the chain. The C—C—C—C torsion angles (about ±179°) of the dodecyl group indicate an antiperiplanar conformation. In the crystal, inversion dimers are formed by pairs of N—H⋯O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benzimidazoles and their derivatives, see: Al Muhaimeed (1997 ); Scott et al. (2002 ); Nakano et al. (2000 ); Zhu et al. (2000 ); Zarrinmayeh et al. (1998 ). For compounds with closely related structures, see: Ouzidan et al. (2011 ); Kandri Rodi et al. (2011 ); Belaziz et al. (2012 ).

Experimental

Crystal data

C₁₉H₃₀N₂O
M_r = 302.45
Monoclinic, C 2/c
a = 38.3223 (14) Å
b = 4.8318 (2) Å
c = 21.9831 (8) Å
β = 117.843 (2)°
V = 3599.3 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.47 × 0.31 × 0.14 mm

Data collection

Bruker X8 APEX Diffractometer
29002 measured reflections
4637 independent reflections
3179 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.141
S = 1.01
4637 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.86	1.97	2.815 (1)	168
Symmetry code: (i) -x, -y+2, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536812041189/im2402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041189/im2402Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041189/im2402Isup3.cml

checkCIF report

Comment top

Benzimidazoles and their derivatives exhibit a number of important pharmacological properties, such as antihistaminic (Al Muhaimeed, 1997) anti-ulcerative (Scott et al., 2002) and antiallergic (Nakano et al., 2000). In addition, benzimidazole derivatives are effective against the human cytomegalovirus (HCMV) (Zhu et al., 2000) and are also efficient selective neuropeptide Y Y1 receptor antagonists (Zarrinmayeh et al., 1998).

In a previous study, we reacted benzimidazol-2-one with octyl bromide in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to form 1-octyl-1H-benzo[d]imidazol-2(3H)-one (Belaziz et al., 2012). The study has been extended to the synthesis of a new benzimidazol-2-one derivative by action of dodecyl bromide with 1H-benzo[d]imidazol-2(3H)-one to form the title compound (Scheme 1).

The molecular structure of 1-dodecyl-1H-benzo[d]imidazol-2(3H)-one is built up from fused six-and five-membered rings linked to a C₁₂H₂₅ chain as shown in Fig. 1. The fused-ring system is essentially planar, with a maximum deviation of -0.013 (2) Å for N2. The dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle between planes (C8 C9 C10) and (N1 N2 C1 to C7) of 82.9 (2)° and by the torsion angle (C7 N2 C8 C9) = -84.3 (2)°. In the crystal structure, inversion dimers are formed by N—H···O hydrogen bonds. in the way to form dimers (Fig. 2).

The structure of the title compound is almost identical to that observed for the following molecules: 1-nonyl-1H-benzimidazol-2(3H)-one, 1-octyl-1H-benzimidazol-2(3H)-one and 5-chloro-1-nonyl-1H-benzimidazol-2(3H)-one (Ouzidan et al., 2011, Kandri Rodi et al. 2011). Nevertheless, the different lengths of the chains leads to different unit cells with different crystal symmetry.

Related literature top

For pharmacological and biochemical properties of benzimidazoles and their derivatives, see: Al Muhaimeed (1997); Scott et al. (2002); Nakano et al. (2000); Zhu et al. (2000); Zarrinmayeh et al. (1998). For compounds with closely related structures, see: Ouzidan et al. (2011); Kandri Rodi et al. (2011); Belaziz et al. (2012).

Experimental top

To 1H-benzo[d]imidazol-2(3H)-one (0.2 g, 1.49 mmol), potassium carbonate (0.41 g, 2.98 mmol) and tetra-n-butylammonium bromide (0.05 g, 0.15 mmol) in DMF (15 ml) was added dodecyl bromide (0.30 ml, 1.78 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 (yield: 65%). The compound was recrystallized from hexan/acetate to give colourless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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. Inversion dimer with molecules linked by N—H···O hydrogen bonds.

1-Dodecyl-1H-benzo[d]imidazol-2(3H)-one top

Crystal data top

C₁₉H₃₀N₂O	F(000) = 1328
M_r = 302.45	D_x = 1.116 Mg m⁻³
Monoclinic, C2/c	Melting point: 346.5 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 38.3223 (14) Å	Cell parameters from 4637 reflections
b = 4.8318 (2) Å	θ = 2.4–28.7°
c = 21.9831 (8) Å	µ = 0.07 mm⁻¹
β = 117.843 (2)°	T = 296 K
V = 3599.3 (2) Å³	Needle, colourless
Z = 8	0.47 × 0.31 × 0.14 mm

Data collection top

Bruker X8 APEX Diffractometer	3179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 28.7°, θ_min = 2.4°
ϕ and ω scans	h = −51→51
29002 measured reflections	k = −6→6
4637 independent reflections	l = −29→28

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0721P)² + 1.030P] where P = (F_o² + 2F_c²)/3
4637 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₃₀N₂O	V = 3599.3 (2) Å³
M_r = 302.45	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 38.3223 (14) Å	µ = 0.07 mm⁻¹
b = 4.8318 (2) Å	T = 296 K
c = 21.9831 (8) Å	0.47 × 0.31 × 0.14 mm
β = 117.843 (2)°

Data collection top

Bruker X8 APEX Diffractometer	3179 reflections with I > 2σ(I)
29002 measured reflections	R_int = 0.028
4637 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.01	Δρ_max = 0.21 e Å⁻³
4637 reflections	Δρ_min = −0.21 e Å⁻³
199 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 > 2σ(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
N2	0.03233 (3)	0.5579 (2)	0.13178 (5)	0.0394 (2)
N1	−0.01601 (3)	0.7314 (2)	0.03782 (5)	0.0398 (2)
H1	−0.0289	0.8297	0.0014	0.048*
O1	0.04750 (2)	0.91076 (19)	0.07646 (4)	0.0472 (2)
C11	0.13888 (4)	0.6345 (3)	0.37748 (6)	0.0440 (3)
H11A	0.1187	0.6113	0.3920	0.053*
H11B	0.1428	0.8315	0.3747	0.053*
C7	−0.00182 (3)	0.4187 (2)	0.12105 (6)	0.0386 (3)
C9	0.08398 (3)	0.6105 (3)	0.25353 (6)	0.0431 (3)
H9A	0.0644	0.5596	0.2679	0.052*
H9B	0.0844	0.8108	0.2510	0.052*
C15	0.24328 (4)	0.5988 (3)	0.62951 (6)	0.0514 (3)
H15A	0.2457	0.7986	0.6294	0.062*
H15B	0.2233	0.5564	0.6435	0.062*
C12	0.17715 (4)	0.5077 (3)	0.43133 (6)	0.0484 (3)
H12A	0.1737	0.3089	0.4317	0.058*
H12B	0.1977	0.5418	0.4182	0.058*
C1	0.02366 (3)	0.7522 (2)	0.08097 (5)	0.0371 (3)
C13	0.19082 (4)	0.6180 (3)	0.50358 (6)	0.0498 (3)
H13A	0.1705	0.5816	0.5171	0.060*
H13B	0.1940	0.8170	0.5032	0.060*
C8	0.07235 (3)	0.4891 (3)	0.18297 (6)	0.0424 (3)
H8A	0.0906	0.5557	0.1671	0.051*
H8B	0.0749	0.2894	0.1870	0.051*
C2	−0.03246 (3)	0.5297 (2)	0.06114 (6)	0.0383 (3)
C10	0.12435 (4)	0.5075 (3)	0.30657 (6)	0.0463 (3)
H10A	0.1232	0.3081	0.3104	0.056*
H10B	0.1433	0.5476	0.2902	0.056*
C17	0.29647 (4)	0.5852 (3)	0.75462 (6)	0.0513 (3)
H17A	0.2983	0.7854	0.7541	0.062*
H17B	0.2769	0.5392	0.7693	0.062*
C14	0.22938 (4)	0.4922 (3)	0.55680 (6)	0.0517 (3)
H14A	0.2497	0.5298	0.5433	0.062*
H14B	0.2262	0.2930	0.5567	0.062*
C16	0.28233 (4)	0.4785 (3)	0.68205 (6)	0.0522 (3)
H16A	0.2798	0.2788	0.6823	0.063*
H16B	0.3022	0.5199	0.6678	0.063*
C6	−0.00851 (4)	0.2120 (3)	0.15747 (7)	0.0493 (3)
H6	0.0118	0.1406	0.1977	0.059*
C3	−0.07051 (4)	0.4301 (3)	0.03570 (7)	0.0490 (3)
H3	−0.0910	0.5015	−0.0044	0.059*
C5	−0.04689 (4)	0.1145 (3)	0.13174 (7)	0.0553 (4)
H5	−0.0524	−0.0248	0.1552	0.066*
C18	0.33590 (4)	0.4716 (3)	0.80666 (7)	0.0616 (4)
H18A	0.3555	0.5176	0.7921	0.074*
H18B	0.3341	0.2714	0.8072	0.074*
C19	0.34981 (5)	0.5790 (4)	0.87888 (7)	0.0774 (5)
H19A	0.3750	0.4990	0.9090	0.116*
H19B	0.3310	0.5294	0.8944	0.116*
H19C	0.3522	0.7768	0.8791	0.116*
C4	−0.07710 (4)	0.2207 (3)	0.07186 (8)	0.0554 (4)
H4	−0.1024	0.1494	0.0556	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N2	0.0357 (5)	0.0440 (5)	0.0272 (4)	0.0014 (4)	0.0053 (4)	0.0030 (4)
N1	0.0355 (5)	0.0458 (6)	0.0282 (4)	0.0032 (4)	0.0065 (4)	0.0038 (4)
O1	0.0404 (4)	0.0546 (5)	0.0378 (4)	−0.0026 (4)	0.0110 (4)	0.0066 (4)
C11	0.0434 (6)	0.0463 (7)	0.0299 (5)	−0.0011 (5)	0.0067 (5)	0.0014 (5)
C7	0.0416 (6)	0.0397 (6)	0.0304 (5)	0.0009 (5)	0.0134 (5)	−0.0038 (4)
C9	0.0410 (6)	0.0450 (7)	0.0305 (6)	0.0040 (5)	0.0061 (5)	0.0011 (5)
C15	0.0462 (7)	0.0619 (8)	0.0314 (6)	−0.0014 (6)	0.0057 (5)	−0.0013 (5)
C12	0.0457 (7)	0.0524 (7)	0.0306 (6)	0.0017 (6)	0.0040 (5)	−0.0013 (5)
C1	0.0373 (6)	0.0405 (6)	0.0267 (5)	0.0026 (5)	0.0092 (4)	−0.0012 (4)
C13	0.0460 (7)	0.0582 (8)	0.0308 (6)	−0.0006 (6)	0.0058 (5)	−0.0010 (5)
C8	0.0366 (6)	0.0470 (7)	0.0302 (6)	0.0069 (5)	0.0044 (5)	0.0026 (5)
C2	0.0396 (6)	0.0404 (6)	0.0309 (5)	0.0014 (5)	0.0131 (5)	−0.0049 (5)
C10	0.0432 (6)	0.0482 (7)	0.0300 (6)	0.0046 (5)	0.0025 (5)	0.0010 (5)
C17	0.0441 (7)	0.0647 (9)	0.0326 (6)	−0.0039 (6)	0.0075 (5)	−0.0003 (6)
C14	0.0478 (7)	0.0579 (8)	0.0314 (6)	−0.0002 (6)	0.0034 (5)	−0.0018 (5)
C16	0.0473 (7)	0.0597 (8)	0.0330 (6)	−0.0001 (6)	0.0048 (5)	−0.0016 (6)
C6	0.0591 (8)	0.0471 (7)	0.0393 (6)	0.0016 (6)	0.0210 (6)	0.0022 (5)
C3	0.0392 (6)	0.0564 (8)	0.0443 (7)	−0.0002 (5)	0.0135 (5)	−0.0078 (6)
C5	0.0690 (9)	0.0500 (8)	0.0572 (8)	−0.0089 (7)	0.0382 (7)	−0.0030 (6)
C18	0.0494 (8)	0.0736 (10)	0.0394 (7)	0.0005 (7)	0.0021 (6)	0.0011 (7)
C19	0.0585 (9)	0.1111 (14)	0.0367 (7)	−0.0096 (9)	0.0006 (7)	0.0009 (8)
C4	0.0502 (8)	0.0569 (8)	0.0632 (9)	−0.0117 (6)	0.0300 (7)	−0.0127 (7)

Geometric parameters (Å, º) top

N2—C1	1.3759 (15)	C8—H8A	0.9700
N2—C7	1.3899 (15)	C8—H8B	0.9700
N2—C8	1.4550 (14)	C2—C3	1.3816 (17)
N1—C1	1.3688 (14)	C10—H10A	0.9700
N1—C2	1.3827 (15)	C10—H10B	0.9700
N1—H1	0.8600	C17—C18	1.5095 (18)
O1—C1	1.2314 (14)	C17—C16	1.5156 (18)
C11—C10	1.5184 (16)	C17—H17A	0.9700
C11—C12	1.5187 (16)	C17—H17B	0.9700
C11—H11A	0.9700	C14—H14A	0.9700
C11—H11B	0.9700	C14—H14B	0.9700
C7—C6	1.3771 (18)	C16—H16A	0.9700
C7—C2	1.3986 (16)	C16—H16B	0.9700
C9—C8	1.5177 (16)	C6—C5	1.3885 (19)
C9—C10	1.5218 (16)	C6—H6	0.9300
C9—H9A	0.9700	C3—C4	1.381 (2)
C9—H9B	0.9700	C3—H3	0.9300
C15—C16	1.5157 (18)	C5—C4	1.383 (2)
C15—C14	1.5195 (18)	C5—H5	0.9300
C15—H15A	0.9700	C18—C19	1.511 (2)
C15—H15B	0.9700	C18—H18A	0.9700
C12—C13	1.5180 (17)	C18—H18B	0.9700
C12—H12A	0.9700	C19—H19A	0.9600
C12—H12B	0.9700	C19—H19B	0.9600
C13—C14	1.5186 (17)	C19—H19C	0.9600
C13—H13A	0.9700	C4—H4	0.9300
C13—H13B	0.9700

C1—N2—C7	109.94 (9)	N1—C2—C7	106.97 (10)
C1—N2—C8	123.45 (10)	C11—C10—C9	114.11 (11)
C7—N2—C8	126.15 (10)	C11—C10—H10A	108.7
C1—N1—C2	110.23 (9)	C9—C10—H10A	108.7
C1—N1—H1	124.9	C11—C10—H10B	108.7
C2—N1—H1	124.9	C9—C10—H10B	108.7
C10—C11—C12	113.25 (11)	H10A—C10—H10B	107.6
C10—C11—H11A	108.9	C18—C17—C16	114.41 (12)
C12—C11—H11A	108.9	C18—C17—H17A	108.7
C10—C11—H11B	108.9	C16—C17—H17A	108.7
C12—C11—H11B	108.9	C18—C17—H17B	108.7
H11A—C11—H11B	107.7	C16—C17—H17B	108.7
C6—C7—N2	131.94 (11)	H17A—C17—H17B	107.6
C6—C7—C2	121.55 (11)	C13—C14—C15	114.31 (12)
N2—C7—C2	106.51 (10)	C13—C14—H14A	108.7
C8—C9—C10	111.39 (10)	C15—C14—H14A	108.7
C8—C9—H9A	109.3	C13—C14—H14B	108.7
C10—C9—H9A	109.3	C15—C14—H14B	108.7
C8—C9—H9B	109.3	H14A—C14—H14B	107.6
C10—C9—H9B	109.3	C17—C16—C15	114.33 (12)
H9A—C9—H9B	108.0	C17—C16—H16A	108.7
C16—C15—C14	114.07 (12)	C15—C16—H16A	108.7
C16—C15—H15A	108.7	C17—C16—H16B	108.7
C14—C15—H15A	108.7	C15—C16—H16B	108.7
C16—C15—H15B	108.7	H16A—C16—H16B	107.6
C14—C15—H15B	108.7	C7—C6—C5	117.30 (12)
H15A—C15—H15B	107.6	C7—C6—H6	121.3
C13—C12—C11	114.18 (11)	C5—C6—H6	121.3
C13—C12—H12A	108.7	C4—C3—C2	117.68 (12)
C11—C12—H12A	108.7	C4—C3—H3	121.2
C13—C12—H12B	108.7	C2—C3—H3	121.2
C11—C12—H12B	108.7	C4—C5—C6	121.22 (13)
H12A—C12—H12B	107.6	C4—C5—H5	119.4
O1—C1—N1	127.98 (10)	C6—C5—H5	119.4
O1—C1—N2	125.67 (10)	C17—C18—C19	114.10 (14)
N1—C1—N2	106.35 (10)	C17—C18—H18A	108.7
C12—C13—C14	113.68 (12)	C19—C18—H18A	108.7
C12—C13—H13A	108.8	C17—C18—H18B	108.7
C14—C13—H13A	108.8	C19—C18—H18B	108.7
C12—C13—H13B	108.8	H18A—C18—H18B	107.6
C14—C13—H13B	108.8	C18—C19—H19A	109.5
H13A—C13—H13B	107.7	C18—C19—H19B	109.5
N2—C8—C9	113.73 (10)	H19A—C19—H19B	109.5
N2—C8—H8A	108.8	C18—C19—H19C	109.5
C9—C8—H8A	108.8	H19A—C19—H19C	109.5
N2—C8—H8B	108.8	H19B—C19—H19C	109.5
C9—C8—H8B	108.8	C3—C4—C5	121.52 (13)
H8A—C8—H8B	107.7	C3—C4—H4	119.2
C3—C2—N1	132.32 (11)	C5—C4—H4	119.2
C3—C2—C7	120.71 (12)

C1—N2—C7—C6	−179.18 (12)	N2—C7—C2—C3	178.75 (10)
C8—N2—C7—C6	8.5 (2)	C6—C7—C2—N1	179.65 (10)
C1—N2—C7—C2	0.61 (13)	N2—C7—C2—N1	−0.17 (12)
C8—N2—C7—C2	−171.76 (10)	C12—C11—C10—C9	174.05 (11)
C10—C11—C12—C13	−176.14 (11)	C8—C9—C10—C11	176.53 (11)
C2—N1—C1—O1	−179.33 (11)	C12—C13—C14—C15	−179.52 (12)
C2—N1—C1—N2	0.70 (12)	C16—C15—C14—C13	−178.39 (12)
C7—N2—C1—O1	179.22 (11)	C18—C17—C16—C15	−178.41 (13)
C8—N2—C1—O1	−8.16 (18)	C14—C15—C16—C17	179.67 (12)
C7—N2—C1—N1	−0.81 (12)	N2—C7—C6—C5	−179.26 (12)
C8—N2—C1—N1	171.81 (10)	C2—C7—C6—C5	0.99 (18)
C11—C12—C13—C14	−179.29 (11)	N1—C2—C3—C4	179.30 (12)
C1—N2—C8—C9	104.30 (13)	C7—C2—C3—C4	0.70 (18)
C7—N2—C8—C9	−84.31 (15)	C7—C6—C5—C4	0.1 (2)
C10—C9—C8—N2	174.01 (10)	C16—C17—C18—C19	179.99 (13)
C1—N1—C2—C3	−179.08 (12)	C2—C3—C4—C5	0.4 (2)
C1—N1—C2—C7	−0.33 (13)	C6—C5—C4—C3	−0.9 (2)
C6—C7—C2—C3	−1.43 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.815 (1)	168

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₃₀N₂O
M_r	302.45
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	38.3223 (14), 4.8318 (2), 21.9831 (8)
β (°)	117.843 (2)
V (Å³)	3599.3 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.47 × 0.31 × 0.14

Data collection
Diffractometer	Bruker X8 APEX Diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29002, 4637, 3179
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.675

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.141, 1.01
No. of reflections	4637
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.21

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.97	2.815 (1)	168.1

Symmetry code: (i) −x, −y+2, −z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

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