1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one

Ouzidan, Y.; Kandri Rodi, Y.; Essassi, E.M.; Luis, S.V.; Bolte, M.; El Ammari, L.

doi:10.1107/S1600536811041389

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2937

doi:10.1107/S1600536811041389

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1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one

Younes Ouzidan,^a ^* Youssef Kandri Rodi,^a El Mokhtar Essassi,^b Santiago V. Luis,^c Michael Bolte ^d and Lahcen El Ammari ^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 URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, ^cDepartamento de Quimica Inorganica & Organica, E.S.T.C.E., Universitat Jaume I, E-12080 Castellon, Spain, ^dInstitut für Anorganische Chemie, J.W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and ^eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: ouzidan@yahoo.fr

(Received 27 September 2011; accepted 7 October 2011; online 12 October 2011)

The title molecule, C₁₇H₂₅N₃O₃, is built up from fused six- and five-membered rings linked to a –C₁₀H₂₁ chain. The fused-ring system is essentially planar, the largest deviation from the mean plane being 0.009 (2) Å. The chain is roughly perpendicular to this plane, making a dihedral angle of 79.5 (2)°. In the crystal, N—H⋯O hydrogen bonds build infinite chains along [010]. There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON [Spek (2009 ). Acta Cryst. D65, 148–155].

Related literature

Experimental

Crystal data

C₁₇H₂₅N₃O₃
M_r = 319.40
Monoclinic, C 2/c
a = 32.9827 (6) Å
b = 4.55881 (9) Å
c = 29.3435 (5) Å
β = 109.481 (2)°
V = 4159.56 (13) Å³
Z = 8
Cu Kα radiation
μ = 0.57 mm⁻¹
T = 206 K
0.15 × 0.11 × 0.05 mm

Data collection

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995 )] T_min = 0.952, T_max = 0.985
20838 measured reflections
4129 independent reflections
3475 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.126
S = 1.09
4129 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.17 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	1.88	2.743 (1)	178
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2011); 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: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811041389/im2324sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041389/im2324Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041389/im2324Isup3.cml

checkCIF report

Comment top

Benzimidazoles are very useful intermediates/subunits for the development of molecules of pharmaceutical or biological interest. Benzimidazole derivatives have found applications in diverse therapeutic areas including anti-ulcers, anti-hypertensives, anti-virals, anti-fungals and anti-cancers (Gravatt et al. 1994; Horton et al. 2003; Kim et al. 1996; Roth et al. 1997).

As a continuation of our research work devoted to the development of substituted benzimidazol-2-one derivatives (Ouzidan et al., 2011a, 2011b), we report in this paper the synthesis of a new benzimidazol-2-one derivative by action of 1-bromodecane with 5-nitro-1,3-dihydro-benzimidazol-2-one in the presence of a catalytic quantity of tetra-n-butylammonium bromide under mild conditions to furnish the title compound (Scheme 1).

The molecular structure of 1-decyl-6-nitro-1,3-dihydro-benzimidazol-2-one is built up from two fused six-and five-membered rings linked to a C₁₀H₂₁ chain as schown in Fg.1. The fused rings are essentially planar, with maximum deviations of 0.008 (2) Å and -0.004 (2) Å for C2 and N1, respectively. The dihedral angle between them does not exceed 0.68 (7)°. The torsional angles C7–N2–C11–C12 and C17–C18–C19–C20 are -98.4 (2) ° and 176.7 (2)°, respectively. N1—H···O1 hydrogen bonds build up infinite one-dimensional chains along the [0 1 0] direction as shown in Fig.2 and Table 1.

Related literature top

For the pharmacological and biochemical properties of related compounds, see: Gravatt et al. (1994); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For related structures, see Ouzidan et al. (2011a,b). There are channels in the structure containing disordered hexane. The contribution of this solvent to the scattering power was suppressed using the SQUEEZE option in PLATON (Spek, 2009).

Experimental top

To 5-nitro-1,3-dihydro-benzimidazol-2-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-bromodecane (0.34 ml, 1.65 mmol). Stirring was continued at room temperature for 6 h. The precipitated salt was removed by filtration and the filtrate was 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 (yield: 27%).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. Packing diagram.

1-Decyl-6-nitro-1H-benzimidazol-2(3H)-one top

Crystal data top

C₁₇H₂₅N₃O₃	F(000) = 1376
M_r = 319.40	D_x = 1.020 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 8979 reflections
a = 32.9827 (6) Å	θ = 2.8–73.1°
b = 4.55881 (9) Å	µ = 0.57 mm⁻¹
c = 29.3435 (5) Å	T = 206 K
β = 109.481 (2)°	Block, colourless
V = 4159.56 (13) Å³	0.15 × 0.11 × 0.05 mm
Z = 8

Data collection top

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer	4129 independent reflections
Radiation source: fine-focus sealed tube	3475 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.029
Detector resolution: 0.4051 pixels mm^-1	θ_max = 73.3°, θ_min = 2.8°
ω scans	h = −40→40
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)]	k = −4→5
T_min = 0.952, T_max = 0.985	l = −36→36
20838 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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0706P)² + 0.8537P] where P = (F_o² + 2F_c²)/3
4129 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₂₅N₃O₃	V = 4159.56 (13) Å³
M_r = 319.40	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 32.9827 (6) Å	µ = 0.57 mm⁻¹
b = 4.55881 (9) Å	T = 206 K
c = 29.3435 (5) Å	0.15 × 0.11 × 0.05 mm
β = 109.481 (2)°

Data collection top

Agilent SuperNova Dual (Cu at zero) Atlas diffractometer	4129 independent reflections
Absorption correction: analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)]	3475 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.985	R_int = 0.029
20838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.09	Δρ_max = 0.16 e Å⁻³
4129 reflections	Δρ_min = −0.17 e Å⁻³
208 parameters

Special details top

Experimental. CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. Clark & Reid (1995).

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
N1	0.76316 (3)	0.5176 (2)	0.70158 (3)	0.0389 (3)
H1	0.7727	0.4612	0.7312	0.047*
N2	0.72508 (3)	0.7438 (2)	0.63471 (3)	0.0319 (2)
N3	0.80707 (4)	0.2956 (3)	0.53894 (4)	0.0493 (3)
O1	0.70806 (3)	0.8310 (2)	0.70415 (3)	0.0459 (3)
O2	0.83330 (4)	0.1068 (3)	0.53903 (4)	0.0817 (4)
O3	0.78870 (3)	0.4442 (2)	0.50339 (3)	0.0571 (3)
C1	0.77940 (3)	0.4278 (3)	0.66624 (4)	0.0337 (3)
C2	0.75516 (3)	0.5736 (3)	0.62357 (4)	0.0304 (3)
C3	0.76366 (3)	0.5367 (3)	0.58100 (4)	0.0341 (3)
H3	0.7482	0.6341	0.5527	0.041*
C4	0.79688 (4)	0.3445 (3)	0.58314 (4)	0.0384 (3)
C5	0.82078 (4)	0.1954 (3)	0.62471 (5)	0.0451 (3)
H5	0.8425	0.0676	0.6240	0.054*
C6	0.81208 (4)	0.2379 (3)	0.66730 (4)	0.0433 (3)
H6	0.8278	0.1413	0.6956	0.052*
C7	0.72984 (3)	0.7087 (3)	0.68291 (4)	0.0350 (3)
C11	0.69093 (3)	0.9198 (3)	0.60136 (4)	0.0325 (3)
H11A	0.7026	1.0276	0.5800	0.039*
H11B	0.6806	1.0613	0.6197	0.039*
C12	0.65344 (3)	0.7327 (3)	0.57121 (4)	0.0342 (3)
H12A	0.6418	0.6247	0.5925	0.041*
H12B	0.6637	0.5915	0.5529	0.041*
C13	0.61786 (4)	0.9169 (3)	0.53654 (4)	0.0355 (3)
H13A	0.6063	1.0490	0.5551	0.043*
H13B	0.6300	1.0352	0.5168	0.043*
C14	0.58145 (4)	0.7315 (3)	0.50369 (4)	0.0380 (3)
H14A	0.5691	0.6155	0.5235	0.046*
H14B	0.5931	0.5970	0.4856	0.046*
C15	0.54594 (4)	0.9122 (3)	0.46821 (4)	0.0403 (3)
H15A	0.5584	1.0310	0.4488	0.048*
H15B	0.5339	1.0442	0.4863	0.048*
C16	0.50987 (4)	0.7262 (3)	0.43470 (5)	0.0409 (3)
H16A	0.5220	0.5927	0.4170	0.049*
H16B	0.4973	0.6089	0.4541	0.049*
C17	0.47449 (4)	0.9044 (3)	0.39880 (5)	0.0417 (3)
H17A	0.4611	1.0287	0.4165	0.050*
H17B	0.4873	1.0311	0.3808	0.050*
C18	0.43994 (4)	0.7188 (3)	0.36328 (5)	0.0444 (3)
H18A	0.4535	0.5884	0.3466	0.053*
H18B	0.4263	0.5982	0.3812	0.053*
C19	0.40558 (4)	0.8947 (3)	0.32606 (5)	0.0530 (4)
H19A	0.3908	1.0171	0.3426	0.064*
H19B	0.4193	1.0233	0.3092	0.064*
C20	0.37271 (5)	0.7073 (4)	0.28924 (6)	0.0673 (5)
H20A	0.3528	0.8315	0.2659	0.101*
H20B	0.3575	0.5894	0.3053	0.101*
H20C	0.3871	0.5820	0.2732	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0368 (5)	0.0594 (7)	0.0176 (4)	−0.0018 (5)	0.0051 (3)	0.0043 (4)
N2	0.0304 (4)	0.0432 (6)	0.0192 (4)	−0.0013 (4)	0.0046 (3)	−0.0007 (4)
N3	0.0505 (6)	0.0633 (8)	0.0392 (6)	0.0032 (6)	0.0218 (5)	−0.0011 (5)
O1	0.0411 (4)	0.0714 (7)	0.0241 (4)	−0.0004 (4)	0.0095 (3)	−0.0087 (4)
O2	0.0945 (9)	0.1005 (10)	0.0648 (7)	0.0446 (8)	0.0461 (7)	0.0090 (7)
O3	0.0644 (6)	0.0789 (8)	0.0333 (5)	0.0066 (5)	0.0236 (4)	0.0067 (5)
C1	0.0310 (5)	0.0458 (7)	0.0217 (5)	−0.0058 (5)	0.0051 (4)	0.0020 (4)
C2	0.0287 (5)	0.0372 (6)	0.0228 (5)	−0.0059 (4)	0.0054 (4)	−0.0003 (4)
C3	0.0357 (5)	0.0422 (7)	0.0227 (5)	−0.0028 (5)	0.0075 (4)	0.0027 (4)
C4	0.0390 (6)	0.0479 (7)	0.0299 (6)	−0.0012 (5)	0.0137 (5)	−0.0006 (5)
C5	0.0398 (6)	0.0542 (8)	0.0399 (6)	0.0078 (6)	0.0115 (5)	0.0037 (6)
C6	0.0393 (6)	0.0544 (8)	0.0312 (6)	0.0046 (6)	0.0050 (5)	0.0098 (5)
C7	0.0316 (5)	0.0510 (7)	0.0199 (5)	−0.0082 (5)	0.0052 (4)	−0.0048 (5)
C11	0.0329 (5)	0.0361 (6)	0.0251 (5)	−0.0005 (5)	0.0050 (4)	−0.0008 (4)
C12	0.0330 (6)	0.0345 (6)	0.0299 (5)	−0.0011 (5)	0.0037 (4)	−0.0006 (5)
C13	0.0330 (5)	0.0337 (7)	0.0341 (6)	0.0002 (5)	0.0037 (4)	−0.0001 (5)
C14	0.0349 (6)	0.0345 (7)	0.0366 (6)	0.0005 (5)	0.0013 (5)	−0.0007 (5)
C15	0.0350 (6)	0.0365 (7)	0.0403 (6)	0.0008 (5)	0.0003 (5)	−0.0010 (5)
C16	0.0367 (6)	0.0362 (7)	0.0403 (6)	0.0005 (5)	0.0000 (5)	−0.0011 (5)
C17	0.0366 (6)	0.0381 (7)	0.0413 (6)	0.0013 (5)	0.0006 (5)	−0.0014 (5)
C18	0.0372 (6)	0.0414 (7)	0.0436 (7)	0.0011 (5)	−0.0011 (5)	−0.0024 (5)
C19	0.0447 (7)	0.0489 (9)	0.0499 (7)	0.0060 (6)	−0.0050 (6)	−0.0026 (6)
C20	0.0483 (8)	0.0687 (11)	0.0608 (9)	0.0079 (7)	−0.0140 (7)	−0.0078 (8)

Geometric parameters (Å, º) top

N1—C7	1.3659 (16)	C13—C14	1.5208 (15)
N1—C1	1.3785 (15)	C13—H13A	0.9700
N1—H1	0.8600	C13—H13B	0.9700
N2—C7	1.3793 (13)	C14—C15	1.5235 (15)
N2—C2	1.3819 (15)	C14—H14A	0.9700
N2—C11	1.4612 (14)	C14—H14B	0.9700
N3—O2	1.2198 (16)	C15—C16	1.5235 (16)
N3—O3	1.2218 (15)	C15—H15A	0.9700
N3—C4	1.4612 (15)	C15—H15B	0.9700
O1—C7	1.2304 (14)	C16—C17	1.5201 (16)
C1—C6	1.3745 (18)	C16—H16A	0.9700
C1—C2	1.4077 (15)	C16—H16B	0.9700
C2—C3	1.3789 (14)	C17—C18	1.5194 (16)
C3—C4	1.3879 (17)	C17—H17A	0.9700
C3—H3	0.9300	C17—H17B	0.9700
C4—C5	1.3890 (17)	C18—C19	1.5148 (17)
C5—C6	1.3862 (18)	C18—H18A	0.9700
C5—H5	0.9300	C18—H18B	0.9700
C6—H6	0.9300	C19—C20	1.5138 (19)
C11—C12	1.5197 (15)	C19—H19A	0.9700
C11—H11A	0.9700	C19—H19B	0.9700
C11—H11B	0.9700	C20—H20A	0.9600
C12—C13	1.5234 (15)	C20—H20B	0.9600
C12—H12A	0.9700	C20—H20C	0.9600
C12—H12B	0.9700

C7—N1—C1	110.52 (9)	C14—C13—H13B	109.0
C7—N1—H1	124.7	C12—C13—H13B	109.0
C1—N1—H1	124.7	H13A—C13—H13B	107.8
C7—N2—C2	109.41 (9)	C13—C14—C15	113.41 (10)
C7—N2—C11	123.32 (9)	C13—C14—H14A	108.9
C2—N2—C11	127.13 (8)	C15—C14—H14A	108.9
O2—N3—O3	122.85 (11)	C13—C14—H14B	108.9
O2—N3—C4	118.60 (11)	C15—C14—H14B	108.9
O3—N3—C4	118.55 (11)	H14A—C14—H14B	107.7
C6—C1—N1	131.94 (10)	C14—C15—C16	113.39 (10)
C6—C1—C2	121.76 (10)	C14—C15—H15A	108.9
N1—C1—C2	106.31 (10)	C16—C15—H15A	108.9
C3—C2—N2	131.46 (10)	C14—C15—H15B	108.9
C3—C2—C1	121.41 (10)	C16—C15—H15B	108.9
N2—C2—C1	107.12 (9)	H15A—C15—H15B	107.7
C2—C3—C4	115.61 (10)	C17—C16—C15	113.80 (10)
C2—C3—H3	122.2	C17—C16—H16A	108.8
C4—C3—H3	122.2	C15—C16—H16A	108.8
C3—C4—C5	123.84 (11)	C17—C16—H16B	108.8
C3—C4—N3	117.89 (10)	C15—C16—H16B	108.8
C5—C4—N3	118.28 (12)	H16A—C16—H16B	107.7
C6—C5—C4	119.74 (12)	C18—C17—C16	113.88 (10)
C6—C5—H5	120.1	C18—C17—H17A	108.8
C4—C5—H5	120.1	C16—C17—H17A	108.8
C1—C6—C5	117.64 (11)	C18—C17—H17B	108.8
C1—C6—H6	121.2	C16—C17—H17B	108.8
C5—C6—H6	121.2	H17A—C17—H17B	107.7
O1—C7—N1	127.86 (10)	C19—C18—C17	114.19 (11)
O1—C7—N2	125.50 (11)	C19—C18—H18A	108.7
N1—C7—N2	106.64 (9)	C17—C18—H18A	108.7
N2—C11—C12	112.17 (10)	C19—C18—H18B	108.7
N2—C11—H11A	109.2	C17—C18—H18B	108.7
C12—C11—H11A	109.2	H18A—C18—H18B	107.6
N2—C11—H11B	109.2	C20—C19—C18	113.67 (12)
C12—C11—H11B	109.2	C20—C19—H19A	108.8
H11A—C11—H11B	107.9	C18—C19—H19A	108.8
C11—C12—C13	112.06 (10)	C20—C19—H19B	108.8
C11—C12—H12A	109.2	C18—C19—H19B	108.8
C13—C12—H12A	109.2	H19A—C19—H19B	107.7
C11—C12—H12B	109.2	C19—C20—H20A	109.5
C13—C12—H12B	109.2	C19—C20—H20B	109.5
H12A—C12—H12B	107.9	H20A—C20—H20B	109.5
C14—C13—C12	112.76 (10)	C19—C20—H20C	109.5
C14—C13—H13A	109.0	H20A—C20—H20C	109.5
C12—C13—H13A	109.0	H20B—C20—H20C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.88	2.743 (1)	178

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₅N₃O₃
M_r	319.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	206
a, b, c (Å)	32.9827 (6), 4.55881 (9), 29.3435 (5)
β (°)	109.481 (2)
V (Å³)	4159.56 (13)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.15 × 0.11 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual (Cu at zero) Atlas diffractometer
Absorption correction	Analytical [CrysAlis PRO (Agilent, 2011) based on expressions derived by Clark & Reid (1995)]
T_min, T_max	0.952, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	20838, 4129, 3475
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.621

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.126, 1.09
No. of reflections	4129
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.88	2.743 (1)	178.2

Symmetry code: (i) −x+3/2, y−1/2, −z+3/2.

References

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Volume 67| Part 11| November 2011| Page o2937

doi:10.1107/S1600536811041389

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