1-Nonyl-1H-benzimidazol-2(3H)-one

Ouzidan, Y.; Kandri Rodi, Y.; Butcher, R.J.; Essassi, E.M.; El Ammari, L.

doi:10.1107/S1600536810054164

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o283

doi:10.1107/S1600536810054164

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1-Nonyl-1H-benzimidazol-2(3H)-one

Younes Ouzidan,^a Youssef Kandri Rodi,^a ^* Raymond J. Butcher,^b El Mokhtar Essassi ^c 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, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cINANOTECH (Institute of Nanomaterials and Nanotechnology), MAScIR, Avenue de l'Armée Royale, 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: kandri_rodi@yahoo.fr

(Received 21 December 2010; accepted 24 December 2010; online 8 January 2011)

The crystal structure of the title compound, C₁₆H₂₄N₂O, is built up from two fused six- and five-membered rings linked to C₉H₁₉ chains. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is nearly perpendicular to this plane [dihedral angle = 80.27 (17)°]. In the crystal, intermolecular N—H⋯O hydrogen bonds form dimers with an R₂²(8) graph-set motif. These dimers are further connected through C—H⋯O hydrogen bonds, building sheets parallel to (100).

Related literature

For the pharmacological and biochemical properties of benzimidazol-2-one derivatives, see: El Azzaoui et al. (2006 ); Soderlind et al. (1999 ); Rémond et al. (1997 ); Gribkoff et al. (1994 ); Olesen et al. (1994 ); McKay et al. (1994 ). For hydrogen-bond motifs, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₂₄N₂O
M_r = 260.37
Monoclinic, P 2₁ /c
a = 18.023 (1) Å
b = 5.4585 (2) Å
c = 16.5708 (9) Å
β = 115.543 (7)°
V = 1470.86 (15) Å³
Z = 4
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 123 K
0.54 × 0.14 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.908, T_max = 0.955
4966 measured reflections
2656 independent reflections
2073 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.06
2656 reflections
177 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1ⁱ	0.92 (2)	1.92 (2)	2.817 (2)	166.1 (19)
C4—H4A⋯O1ⁱⁱ	0.95	2.50	3.284 (2)	140
C8—H8B⋯O1ⁱⁱⁱ	0.99	2.55	3.453 (2)	151
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054164/dn2641sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054164/dn2641Isup2.hkl

checkCIF report

Comment top

Benzimidazol-2-one derivatives are useful heterocyclic building blocks (El Azzaoui et al.,2006) and are prominent structural elements of compounds demonstrating a wide variety of pharmacological and biochemical properties (Soderlind et al.,1999). Examples of pharmacological activity exhibited by benzimidazol-2-ones include antagonism of neurotransmitter receptors, inhibition of aldose reductase, antiulcer and antisecretory properties, and modulation of ion channels. (Rémond et al., (1997); Gribkoff et al., (1994); Olesen et al., (1994); McKay et al., (1994).

The 1-nonyl-1H-benzimidazol-2(3H)-one molecule structure is built up from two fused six-and five-membered rings linked to C₉H₁₉ chains as schown in Fg.1. The fused-ring system is essentially planar, with a maximum deviation of 0.005 (2) Å and -0.009 (2) Å for C7 and N1 respectyvely. The dihedral angle between them does not exceed 1.03 (6)°. The torsion angles C1 N1 C8 C9 and C11 C12 C13 C14 are 113.4 (2)° and 178.9 (2)° respectively.

N-H···O hydrogen bonds result in the formation of dimers with R₂²(8) graph set motif (Etter et al., 1990; Bernstein et al., 1995). These dimer are further connected through C-H···O hydrogen bonds building sheets parallell to the (1 0 0) plane. (Table 1).

Related literature top

For the pharmacological and biochemical properties of benzimidazol-2-one derivatives, see: El Azzaoui et al. (2006); Soderlind et al. (1999); Rémond et al. (1997); Gribkoff et al. (1994); Olesen et al. (1994); McKay et al. (1994). For hydrogen-bond motifs, see: Etter et al. (1990); Bernstein et al. (1995) .

Experimental top

To benzimidazol-2-one (0,21 g, 1,5 mmol), potassium carbonate (0,41 g, 3 mmol), and tetra-n-butylammonium bromide (0.1 g, 0,3 mmol) in DMF (15 ml) was added 1-bromononane (0,57 ml, 3 mmol). Stirring was continued at room temperature for 6 h. The salts were 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 crystals were isolated when the solvent was allowed to evaporate.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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: WinGX (Farrugia, 1999).

Figures top

Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

1-Nonyl-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₆H₂₄N₂O	F(000) = 568
M_r = 260.37	D_x = 1.176 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 2656 reflections
a = 18.023 (1) Å	θ = 5.3–67.7°
b = 5.4585 (2) Å	µ = 0.57 mm⁻¹
c = 16.5708 (9) Å	T = 123 K
β = 115.543 (7)°	Needle, colorless
V = 1470.86 (15) Å³	0.54 × 0.14 × 0.08 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2656 independent reflections
Radiation source: Enhance (Cu) X-ray Source	2073 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 10.5081 pixels mm^-1	θ_max = 67.7°, θ_min = 5.3°
ω scans	h = −21→14
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −6→5
T_min = 0.908, T_max = 0.955	l = −15→19
4966 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0758P)² + 0.0676P] where P = (F_o² + 2F_c²)/3
2656 reflections	(Δ/σ)_max < 0.001
177 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₆H₂₄N₂O	V = 1470.86 (15) Å³
M_r = 260.37	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 18.023 (1) Å	µ = 0.57 mm⁻¹
b = 5.4585 (2) Å	T = 123 K
c = 16.5708 (9) Å	0.54 × 0.14 × 0.08 mm
β = 115.543 (7)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	2656 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2073 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.955	R_int = 0.038
4966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.24 e Å⁻³
2656 reflections	Δρ_min = −0.23 e Å⁻³
177 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction Ltd (2010). Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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
O1	0.04944 (8)	0.7205 (2)	0.58716 (8)	0.0258 (3)
N1	0.11884 (9)	0.9981 (3)	0.53791 (9)	0.0227 (3)
N2	0.05350 (9)	0.6926 (3)	0.44838 (9)	0.0238 (3)
H2N	0.0218 (14)	0.554 (4)	0.4288 (14)	0.040 (6)*
C1	0.07126 (10)	0.7949 (3)	0.53033 (11)	0.0217 (4)
C2	0.08761 (11)	0.8328 (3)	0.40292 (11)	0.0231 (4)
C3	0.08572 (11)	0.8103 (3)	0.31892 (12)	0.0269 (4)
H3A	0.0576	0.6787	0.2803	0.032*
C4	0.12671 (11)	0.9882 (3)	0.29310 (12)	0.0285 (4)
H4A	0.1271	0.9765	0.2361	0.034*
C5	0.16711 (12)	1.1829 (3)	0.34929 (12)	0.0288 (4)
H5A	0.1941	1.3020	0.3296	0.035*
C6	0.16872 (11)	1.2065 (3)	0.43378 (12)	0.0256 (4)
H6A	0.1960	1.3396	0.4720	0.031*
C7	0.12889 (10)	1.0278 (3)	0.45958 (11)	0.0228 (4)
C8	0.14782 (11)	1.1628 (3)	0.61482 (11)	0.0237 (4)
H8A	0.1212	1.1168	0.6539	0.028*
H8B	0.1306	1.3320	0.5935	0.028*
C9	0.24066 (11)	1.1583 (3)	0.66960 (11)	0.0244 (4)
H9A	0.2555	1.2741	0.7202	0.029*
H9B	0.2670	1.2171	0.6317	0.029*
C10	0.27540 (11)	0.9070 (3)	0.70653 (12)	0.0282 (4)
H10A	0.2660	0.7946	0.6561	0.034*
H10B	0.2457	0.8404	0.7399	0.034*
C11	0.36729 (11)	0.9157 (4)	0.76838 (12)	0.0287 (4)
H11A	0.3963	0.9927	0.7360	0.034*
H11B	0.3761	1.0207	0.8204	0.034*
C12	0.40510 (11)	0.6654 (4)	0.80204 (12)	0.0304 (4)
H12A	0.3996	0.5635	0.7503	0.036*
H12B	0.3741	0.5839	0.8314	0.036*
C13	0.49577 (12)	0.6790 (4)	0.86815 (12)	0.0300 (4)
H13A	0.5267	0.7583	0.8383	0.036*
H13B	0.5012	0.7841	0.9191	0.036*
C14	0.53471 (11)	0.4315 (3)	0.90421 (12)	0.0301 (4)
H14A	0.5305	0.3269	0.8536	0.036*
H14B	0.5035	0.3506	0.9335	0.036*
C15	0.62484 (11)	0.4504 (4)	0.97121 (12)	0.0314 (4)
H15A	0.6556	0.5360	0.9425	0.038*
H15B	0.6288	0.5511	1.0226	0.038*
C16	0.66513 (13)	0.2034 (4)	1.00569 (14)	0.0392 (5)
H16A	0.7224	0.2283	1.0491	0.059*
H16B	0.6637	0.1050	0.9556	0.059*
H16C	0.6353	0.1176	1.0346	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0284 (7)	0.0254 (7)	0.0233 (6)	−0.0011 (5)	0.0109 (5)	0.0012 (5)
N1	0.0246 (8)	0.0227 (8)	0.0190 (7)	0.0001 (6)	0.0077 (6)	0.0002 (6)
N2	0.0242 (8)	0.0228 (8)	0.0225 (8)	−0.0017 (6)	0.0083 (6)	−0.0009 (6)
C1	0.0202 (8)	0.0209 (8)	0.0214 (8)	0.0037 (7)	0.0066 (7)	0.0018 (7)
C2	0.0203 (8)	0.0227 (9)	0.0241 (9)	0.0019 (7)	0.0075 (7)	0.0012 (7)
C3	0.0265 (9)	0.0269 (10)	0.0231 (9)	0.0010 (7)	0.0065 (7)	−0.0024 (7)
C4	0.0306 (10)	0.0331 (10)	0.0216 (8)	0.0037 (8)	0.0112 (8)	0.0025 (8)
C5	0.0301 (10)	0.0290 (10)	0.0283 (10)	0.0003 (8)	0.0135 (8)	0.0044 (7)
C6	0.0254 (9)	0.0227 (9)	0.0258 (9)	−0.0010 (7)	0.0082 (7)	−0.0005 (7)
C7	0.0211 (9)	0.0246 (9)	0.0202 (8)	0.0048 (7)	0.0065 (7)	0.0026 (7)
C8	0.0266 (9)	0.0224 (9)	0.0203 (8)	0.0009 (7)	0.0083 (7)	−0.0006 (7)
C9	0.0257 (9)	0.0246 (9)	0.0218 (9)	−0.0014 (7)	0.0093 (7)	−0.0015 (7)
C10	0.0258 (10)	0.0274 (10)	0.0272 (9)	−0.0001 (8)	0.0076 (8)	0.0010 (7)
C11	0.0253 (10)	0.0310 (10)	0.0254 (9)	−0.0003 (8)	0.0066 (8)	0.0017 (7)
C12	0.0274 (10)	0.0312 (10)	0.0281 (9)	−0.0006 (8)	0.0077 (8)	0.0008 (8)
C13	0.0267 (10)	0.0304 (10)	0.0279 (10)	0.0013 (8)	0.0071 (8)	0.0026 (8)
C14	0.0272 (10)	0.0307 (10)	0.0293 (9)	0.0007 (8)	0.0092 (8)	0.0022 (8)
C15	0.0278 (10)	0.0320 (10)	0.0299 (10)	0.0015 (8)	0.0080 (8)	0.0030 (8)
C16	0.0313 (11)	0.0384 (12)	0.0405 (12)	0.0061 (9)	0.0084 (9)	0.0048 (9)

Geometric parameters (Å, º) top

O1—C1	1.235 (2)	C9—H9B	0.9900
N1—C1	1.375 (2)	C10—C11	1.527 (2)
N1—C7	1.395 (2)	C10—H10A	0.9900
N1—C8	1.460 (2)	C10—H10B	0.9900
N2—C1	1.372 (2)	C11—C12	1.522 (3)
N2—C2	1.389 (2)	C11—H11A	0.9900
N2—H2N	0.92 (2)	C11—H11B	0.9900
C2—C3	1.383 (2)	C12—C13	1.527 (3)
C2—C7	1.402 (2)	C12—H12A	0.9900
C3—C4	1.395 (3)	C12—H12B	0.9900
C3—H3A	0.9500	C13—C14	1.521 (3)
C4—C5	1.393 (3)	C13—H13A	0.9900
C4—H4A	0.9500	C13—H13B	0.9900
C5—C6	1.394 (2)	C14—C15	1.525 (2)
C5—H5A	0.9500	C14—H14A	0.9900
C6—C7	1.384 (2)	C14—H14B	0.9900
C6—H6A	0.9500	C15—C16	1.521 (3)
C8—C9	1.521 (2)	C15—H15A	0.9900
C8—H8A	0.9900	C15—H15B	0.9900
C8—H8B	0.9900	C16—H16A	0.9800
C9—C10	1.523 (2)	C16—H16B	0.9800
C9—H9A	0.9900	C16—H16C	0.9800

C1—N1—C7	109.57 (14)	C11—C10—H10A	109.1
C1—N1—C8	123.43 (14)	C9—C10—H10B	109.1
C7—N1—C8	126.84 (15)	C11—C10—H10B	109.1
C1—N2—C2	110.10 (15)	H10A—C10—H10B	107.9
C1—N2—H2N	121.8 (13)	C12—C11—C10	113.73 (16)
C2—N2—H2N	128.0 (13)	C12—C11—H11A	108.8
O1—C1—N2	127.30 (17)	C10—C11—H11A	108.8
O1—C1—N1	125.93 (16)	C12—C11—H11B	108.8
N2—C1—N1	106.77 (14)	C10—C11—H11B	108.8
C3—C2—N2	132.22 (17)	H11A—C11—H11B	107.7
C3—C2—C7	121.15 (16)	C11—C12—C13	113.00 (16)
N2—C2—C7	106.63 (15)	C11—C12—H12A	109.0
C2—C3—C4	117.41 (17)	C13—C12—H12A	109.0
C2—C3—H3A	121.3	C11—C12—H12B	109.0
C4—C3—H3A	121.3	C13—C12—H12B	109.0
C5—C4—C3	121.29 (16)	H12A—C12—H12B	107.8
C5—C4—H4A	119.4	C14—C13—C12	114.10 (16)
C3—C4—H4A	119.4	C14—C13—H13A	108.7
C4—C5—C6	121.35 (17)	C12—C13—H13A	108.7
C4—C5—H5A	119.3	C14—C13—H13B	108.7
C6—C5—H5A	119.3	C12—C13—H13B	108.7
C7—C6—C5	117.15 (17)	H13A—C13—H13B	107.6
C7—C6—H6A	121.4	C13—C14—C15	113.07 (16)
C5—C6—H6A	121.4	C13—C14—H14A	109.0
C6—C7—N1	131.46 (16)	C15—C14—H14A	109.0
C6—C7—C2	121.64 (16)	C13—C14—H14B	109.0
N1—C7—C2	106.89 (15)	C15—C14—H14B	109.0
N1—C8—C9	113.48 (14)	H14A—C14—H14B	107.8
N1—C8—H8A	108.9	C16—C15—C14	113.53 (17)
C9—C8—H8A	108.9	C16—C15—H15A	108.9
N1—C8—H8B	108.9	C14—C15—H15A	108.9
C9—C8—H8B	108.9	C16—C15—H15B	108.9
H8A—C8—H8B	107.7	C14—C15—H15B	108.9
C8—C9—C10	114.21 (15)	H15A—C15—H15B	107.7
C8—C9—H9A	108.7	C15—C16—H16A	109.5
C10—C9—H9A	108.7	C15—C16—H16B	109.5
C8—C9—H9B	108.7	H16A—C16—H16B	109.5
C10—C9—H9B	108.7	C15—C16—H16C	109.5
H9A—C9—H9B	107.6	H16A—C16—H16C	109.5
C9—C10—C11	112.36 (16)	H16B—C16—H16C	109.5
C9—C10—H10A	109.1

C2—N2—C1—O1	178.67 (16)	C8—N1—C7—C6	2.0 (3)
C2—N2—C1—N1	−1.54 (18)	C1—N1—C7—C2	−1.36 (18)
C7—N1—C1—O1	−178.42 (16)	C8—N1—C7—C2	−176.97 (15)
C8—N1—C1—O1	−2.6 (3)	C3—C2—C7—C6	0.6 (3)
C7—N1—C1—N2	1.78 (18)	N2—C2—C7—C6	−178.71 (16)
C8—N1—C1—N2	177.57 (14)	C3—C2—C7—N1	179.70 (15)
C1—N2—C2—C3	−178.49 (18)	N2—C2—C7—N1	0.39 (18)
C1—N2—C2—C7	0.71 (19)	C1—N1—C8—C9	113.44 (17)
N2—C2—C3—C4	179.37 (18)	C7—N1—C8—C9	−71.5 (2)
C7—C2—C3—C4	0.3 (2)	N1—C8—C9—C10	−58.51 (19)
C2—C3—C4—C5	−0.8 (3)	C8—C9—C10—C11	−174.43 (14)
C3—C4—C5—C6	0.5 (3)	C9—C10—C11—C12	−176.51 (15)
C4—C5—C6—C7	0.3 (3)	C10—C11—C12—C13	−176.55 (14)
C5—C6—C7—N1	−179.73 (17)	C11—C12—C13—C14	178.92 (15)
C5—C6—C7—C2	−0.9 (3)	C12—C13—C14—C15	−179.06 (15)
C1—N1—C7—C6	177.62 (18)	C13—C14—C15—C16	−178.32 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.92 (2)	1.92 (2)	2.817 (2)	166.1 (19)
C4—H4A···O1ⁱⁱ	0.95	2.50	3.284 (2)	140
C8—H8B···O1ⁱⁱⁱ	0.99	2.55	3.453 (2)	151

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₄N₂O
M_r	260.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	123
a, b, c (Å)	18.023 (1), 5.4585 (2), 16.5708 (9)
β (°)	115.543 (7)
V (Å³)	1470.86 (15)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.54 × 0.14 × 0.08

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.908, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	4966, 2656, 2073
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.06
No. of reflections	2656
No. of parameters	177
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1ⁱ	0.92 (2)	1.92 (2)	2.817 (2)	166.1 (19)
C4—H4A···O1ⁱⁱ	0.95	2.50	3.284 (2)	140
C8—H8B···O1ⁱⁱⁱ	0.99	2.55	3.453 (2)	151

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) x, y+1, z.

References

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Volume 67| Part 2| February 2011| Page o283

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