N-Cyclo­hexyl-3,4,5-trimethoxy­benzamide

Saeed, A.; Arshad, M.; Khera, R.A.; Bolte, M.

doi:10.1107/S1600536809050284

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3234

doi:10.1107/S1600536809050284

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N-Cyclohexyl-3,4,5-trimethoxybenzamide

Aamer Saeed,^a ^* Muhammad Arshad,^b Rasheed Ahmad Khera ^a and Michael Bolte ^c

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, ^bChemistry Division, Directorate of Science, PINSTECH, Nilore, Islamabad, Pakistan, and ^cInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: aamersaeed@yahoo.com

(Received 11 November 2009; accepted 23 November 2009; online 28 November 2009)

The 3,5-methoxy groups in the title compound, C₁₆H₂₃NO₄, are almost coplanar with the aromatic ring, whereas the 4-methoxy group is bent out of this plane. The three CH₃—O—C—C torsion angles are −1.51 (18), 0.73 (19) and 75.33 (15)°. The cyclohexane ring adopts a chair conformation. In the crystal, molecules are connected by intermolecular N—H⋯O hydrogen bonds into chains running along the b axis.

Related literature

For the biological activity of benzanilides, see: Olsson et al. (2002 ); Lindgren et al. (2001 ); Calderone et al. (2006 ). For the use of benzamides in organic synthesis, see: Zhichkin et al. (2007 ); Beccalli et al. (2005 ). For related structures, see: Bowes et al. (2003 ); Chopra & Guru Row (2008 ); Kashino et al. (1979 ); Saeed et al. (2008 ).

Experimental

Crystal data

C₁₆H₂₃NO₄
M_r = 293.35
Monoclinic, P 2₁ /c
a = 23.4539 (19) Å
b = 5.2145 (6) Å
c = 12.4559 (10) Å
β = 92.886 (6)°
V = 1521.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 K
0.37 × 0.37 × 0.33 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: none
6868 measured reflections
2823 independent reflections
2360 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.109
S = 1.05
2823 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.916 (19)	2.153 (19)	3.0262 (15)	159.0 (15)
Symmetry code: (i) x, y+1, z.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ) and SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050284/fj2261sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809050284/fj2261Isup2.hkl

checkCIF report

Comment top

N-substituted benzamides are well known anticancer compounds and the mechanism of action for N-substituted benzamide-induced apoptosis has been studied, using declopramide as a lead compound (Olsson et al., 2002). N-substituted benzamides inhibit the activity of nuclear factor- B and nuclear factor of activated T cells activity while inducing activator protein 1 activity in T lymphocytes (Lindgren et al., 2001). Heterocyclic analogs of benzanilide derivatives are potassium channel activators (Calderone et al., 2006). N-Alkylated 2-nitrobenzamides are intermediates in the synthesis of dibenzo[b,e][1,4]diazepines (Zhichkin et al., 2007) and N-Acyl-2-nitrobenzamides are precursors of 2,3-disubstitued 3H-quinazoline-4-ones (Beccalli et al., 2005).

The two m-methoxy groups the title compound are almost coplanar with the aromatic ring [CH₃—O—C—C -1.51 (18)° and 0.73 (19)°] whereas the methoxy group in para position is bent out of the plane of the aromatic ring [CH₃—O—C—C 75.33 (15)°]. The cyclohexyl ring adops a chair conformation. The molecules are connected by N—H···O hydrogen bonds to chains running along the b axis.

Related literature top

For the biological activity of benzanilides, see: Olsson et al. (2002); Lindgren et al. (2001); Calderone et al. (2006). For the use of benzamides in organic synthesis, see: Zhichkin et al. (2007); Beccalli et al. (2005). For related structures, see: Bowes et al. (2003); Chopra & Row (2008); Kashino et al. (1979); Saeed et al. (2008).

Experimental top

3,4,5-Trimethoxybenzoyl chloride (1 mmol) in CHCl₃ was treated with cyclohexylamine (3.5 mmol) under a nitrogen atmosphere at reflux for 3 h. Upon cooling, the reaction mixture was diluted with CHCl₃ and washed consecutively with 1 M aq HCl and saturated aq NaHCO₃. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in methanol afforded the title compound (78%) as colourless crystals: Anal. calcd. for C₁₆H₂₃N_O4: C, 65.51; H, 9.70; N, 4.77%; found: C, 65.58; H, 9.65; N, 4.81%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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: PLATON (Spek, 2009) and SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing viewed along [001] with intermolecular hydrogen bonds indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

N-Cyclohexyl-3,4,5-trimethoxybenzamide top

Crystal data top

C₁₆H₂₃NO₄	F(000) = 632
M_r = 293.35	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6103 reflections
a = 23.4539 (19) Å	θ = 3.4–26.0°
b = 5.2145 (6) Å	µ = 0.09 mm⁻¹
c = 12.4559 (10) Å	T = 173 K
β = 92.886 (6)°	Block, colourless
V = 1521.4 (2) Å³	0.37 × 0.37 × 0.33 mm
Z = 4

Data collection top

Stoe IPDSII two-circle diffractometer	2360 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.062
Graphite monochromator	θ_max = 25.6°, θ_min = 3.4°
ω scans	h = −28→23
6868 measured reflections	k = −5→6
2823 independent reflections	l = −15→15

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 atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0651P)² + 0.0617P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2823 reflections	Δρ_max = 0.27 e Å⁻³
198 parameters	Δρ_min = −0.22 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 (3)

Crystal data top

C₁₆H₂₃NO₄	V = 1521.4 (2) Å³
M_r = 293.35	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 23.4539 (19) Å	µ = 0.09 mm⁻¹
b = 5.2145 (6) Å	T = 173 K
c = 12.4559 (10) Å	0.37 × 0.37 × 0.33 mm
β = 92.886 (6)°

Data collection top

Stoe IPDSII two-circle diffractometer	2360 reflections with I > 2σ(I)
6868 measured reflections	R_int = 0.062
2823 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
2823 reflections	Δρ_min = −0.22 e Å⁻³
198 parameters

Special details top

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 > 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	0.19554 (5)	0.4159 (2)	0.53398 (9)	0.0237 (3)
H1	0.2089 (8)	0.579 (4)	0.5241 (13)	0.034 (4)*
O1	0.21507 (4)	−0.01048 (18)	0.53804 (8)	0.0289 (3)
O2	0.42937 (4)	0.00520 (19)	0.45580 (7)	0.0279 (3)
O3	0.43346 (4)	0.36344 (18)	0.30218 (7)	0.0242 (2)
O4	0.34531 (4)	0.66623 (18)	0.25120 (7)	0.0255 (2)
C1	0.22841 (6)	0.2119 (2)	0.51372 (10)	0.0211 (3)
C11	0.28301 (5)	0.2637 (2)	0.45950 (9)	0.0198 (3)
C12	0.32948 (6)	0.1047 (2)	0.48557 (9)	0.0213 (3)
H12	0.3265	−0.0265	0.5379	0.026*
C13	0.38033 (6)	0.1395 (3)	0.43442 (9)	0.0211 (3)
C14	0.38357 (5)	0.3267 (2)	0.35373 (9)	0.0202 (3)
C15	0.33712 (6)	0.4871 (2)	0.32918 (9)	0.0198 (3)
C16	0.28646 (6)	0.4586 (2)	0.38262 (9)	0.0201 (3)
H16	0.2550	0.5693	0.3671	0.024*
C17	0.42929 (6)	−0.1910 (3)	0.53660 (10)	0.0268 (3)
H17A	0.4199	−0.1149	0.6055	0.040*
H17B	0.4671	−0.2707	0.5438	0.040*
H17C	0.4008	−0.3214	0.5157	0.040*
C18	0.44384 (6)	0.1648 (3)	0.22488 (11)	0.0294 (3)
H18A	0.4411	−0.0034	0.2593	0.044*
H18B	0.4821	0.1863	0.1981	0.044*
H18C	0.4154	0.1767	0.1647	0.044*
C19	0.29830 (6)	0.8303 (3)	0.22110 (10)	0.0258 (3)
H19A	0.2659	0.7263	0.1939	0.039*
H19B	0.3095	0.9489	0.1649	0.039*
H19C	0.2873	0.9282	0.2839	0.039*
C21	0.14322 (6)	0.3901 (3)	0.59287 (11)	0.0247 (3)
H21	0.1261	0.2185	0.5755	0.030*
C22	0.15657 (7)	0.4025 (4)	0.71420 (11)	0.0376 (4)
H22A	0.1758	0.5670	0.7323	0.045*
H22B	0.1831	0.2617	0.7357	0.045*
C23	0.10231 (7)	0.3799 (4)	0.77699 (12)	0.0404 (4)
H23A	0.0851	0.2082	0.7649	0.048*
H23B	0.1122	0.3984	0.8548	0.048*
C24	0.05945 (7)	0.5845 (3)	0.74171 (12)	0.0372 (4)
H24A	0.0750	0.7557	0.7612	0.045*
H24B	0.0239	0.5599	0.7800	0.045*
C25	0.04589 (7)	0.5735 (4)	0.62060 (12)	0.0376 (4)
H25A	0.0196	0.7153	0.5994	0.045*
H25B	0.0264	0.4097	0.6023	0.045*
C26	0.10009 (6)	0.5950 (3)	0.55750 (11)	0.0310 (3)
H26A	0.0901	0.5757	0.4797	0.037*
H26B	0.1173	0.7668	0.5692	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0193 (6)	0.0209 (6)	0.0316 (6)	−0.0013 (5)	0.0099 (4)	0.0005 (4)
O1	0.0248 (5)	0.0215 (5)	0.0413 (6)	−0.0004 (4)	0.0099 (4)	0.0034 (4)
O2	0.0198 (5)	0.0365 (6)	0.0277 (5)	0.0075 (4)	0.0047 (4)	0.0091 (4)
O3	0.0189 (5)	0.0278 (5)	0.0266 (5)	−0.0017 (4)	0.0083 (4)	−0.0024 (4)
O4	0.0250 (5)	0.0272 (5)	0.0248 (4)	0.0026 (4)	0.0065 (4)	0.0070 (4)
C1	0.0188 (6)	0.0230 (6)	0.0215 (6)	−0.0005 (5)	0.0011 (5)	−0.0006 (5)
C11	0.0184 (6)	0.0221 (6)	0.0192 (5)	−0.0026 (5)	0.0036 (5)	−0.0048 (5)
C12	0.0218 (7)	0.0225 (6)	0.0197 (6)	−0.0007 (5)	0.0030 (5)	0.0009 (5)
C13	0.0175 (6)	0.0248 (6)	0.0210 (6)	0.0015 (5)	0.0007 (5)	−0.0025 (5)
C14	0.0172 (6)	0.0240 (6)	0.0197 (6)	−0.0025 (5)	0.0039 (5)	−0.0035 (5)
C15	0.0214 (7)	0.0205 (6)	0.0178 (6)	−0.0012 (5)	0.0024 (5)	−0.0011 (4)
C16	0.0176 (6)	0.0212 (6)	0.0215 (6)	0.0018 (5)	0.0009 (5)	−0.0017 (5)
C17	0.0278 (7)	0.0269 (7)	0.0254 (6)	0.0054 (6)	−0.0003 (5)	0.0037 (5)
C18	0.0293 (8)	0.0299 (7)	0.0301 (7)	0.0031 (6)	0.0125 (6)	−0.0023 (6)
C19	0.0287 (7)	0.0255 (7)	0.0233 (6)	0.0040 (6)	0.0007 (5)	0.0033 (5)
C21	0.0190 (7)	0.0246 (7)	0.0312 (7)	−0.0017 (6)	0.0086 (5)	−0.0003 (5)
C22	0.0250 (8)	0.0572 (10)	0.0312 (8)	0.0053 (7)	0.0064 (6)	0.0073 (7)
C23	0.0338 (9)	0.0543 (10)	0.0342 (8)	0.0028 (8)	0.0124 (7)	0.0066 (7)
C24	0.0318 (8)	0.0385 (9)	0.0431 (8)	−0.0008 (7)	0.0184 (7)	−0.0058 (7)
C25	0.0218 (8)	0.0462 (9)	0.0456 (9)	0.0068 (7)	0.0085 (6)	0.0034 (7)
C26	0.0238 (8)	0.0352 (8)	0.0346 (7)	0.0050 (6)	0.0073 (6)	0.0057 (6)

Geometric parameters (Å, º) top

N1—C1	1.3451 (17)	C18—H18B	0.9800
N1—C21	1.4670 (16)	C18—H18C	0.9800
N1—H1	0.916 (19)	C19—H19A	0.9800
O1—C1	1.2424 (16)	C19—H19B	0.9800
O2—C13	1.3615 (16)	C19—H19C	0.9800
O2—C17	1.4353 (16)	C21—C26	1.521 (2)
O3—C14	1.3761 (15)	C21—C22	1.529 (2)
O3—C18	1.4432 (16)	C21—H21	1.0000
O4—C15	1.3681 (15)	C22—C23	1.532 (2)
O4—C19	1.4307 (17)	C22—H22A	0.9900
C1—C11	1.5020 (17)	C22—H22B	0.9900
C11—C12	1.3945 (19)	C23—C24	1.516 (2)
C11—C16	1.4015 (18)	C23—H23A	0.9900
C12—C13	1.3920 (18)	C23—H23B	0.9900
C12—H12	0.9500	C24—C25	1.527 (2)
C13—C14	1.4058 (18)	C24—H24A	0.9900
C14—C15	1.3951 (19)	C24—H24B	0.9900
C15—C16	1.3988 (18)	C25—C26	1.5320 (19)
C16—H16	0.9500	C25—H25A	0.9900
C17—H17A	0.9800	C25—H25B	0.9900
C17—H17B	0.9800	C26—H26A	0.9900
C17—H17C	0.9800	C26—H26B	0.9900
C18—H18A	0.9800

C1—N1—C21	121.53 (11)	H19A—C19—H19B	109.5
C1—N1—H1	120.3 (11)	O4—C19—H19C	109.5
C21—N1—H1	117.0 (11)	H19A—C19—H19C	109.5
C13—O2—C17	118.23 (10)	H19B—C19—H19C	109.5
C14—O3—C18	112.80 (10)	N1—C21—C26	110.57 (11)
C15—O4—C19	117.42 (10)	N1—C21—C22	110.82 (11)
O1—C1—N1	122.58 (12)	C26—C21—C22	110.89 (12)
O1—C1—C11	120.55 (12)	N1—C21—H21	108.1
N1—C1—C11	116.87 (11)	C26—C21—H21	108.1
C12—C11—C16	121.26 (11)	C22—C21—H21	108.2
C12—C11—C1	117.54 (11)	C21—C22—C23	111.55 (13)
C16—C11—C1	121.16 (11)	C21—C22—H22A	109.3
C13—C12—C11	119.56 (11)	C23—C22—H22A	109.3
C13—C12—H12	120.2	C21—C22—H22B	109.3
C11—C12—H12	120.2	C23—C22—H22B	109.3
O2—C13—C12	125.32 (11)	H22A—C22—H22B	108.0
O2—C13—C14	114.92 (11)	C24—C23—C22	110.72 (13)
C12—C13—C14	119.75 (12)	C24—C23—H23A	109.5
O3—C14—C15	119.15 (11)	C22—C23—H23A	109.5
O3—C14—C13	120.54 (12)	C24—C23—H23B	109.5
C15—C14—C13	120.22 (11)	C22—C23—H23B	109.5
O4—C15—C14	115.40 (11)	H23A—C23—H23B	108.1
O4—C15—C16	124.30 (12)	C23—C24—C25	111.23 (13)
C14—C15—C16	120.29 (11)	C23—C24—H24A	109.4
C15—C16—C11	118.82 (12)	C25—C24—H24A	109.4
C15—C16—H16	120.6	C23—C24—H24B	109.4
C11—C16—H16	120.6	C25—C24—H24B	109.4
O2—C17—H17A	109.5	H24A—C24—H24B	108.0
O2—C17—H17B	109.5	C24—C25—C26	111.54 (13)
H17A—C17—H17B	109.5	C24—C25—H25A	109.3
O2—C17—H17C	109.5	C26—C25—H25A	109.3
H17A—C17—H17C	109.5	C24—C25—H25B	109.3
H17B—C17—H17C	109.5	C26—C25—H25B	109.3
O3—C18—H18A	109.5	H25A—C25—H25B	108.0
O3—C18—H18B	109.5	C21—C26—C25	110.91 (12)
H18A—C18—H18B	109.5	C21—C26—H26A	109.5
O3—C18—H18C	109.5	C25—C26—H26A	109.5
H18A—C18—H18C	109.5	C21—C26—H26B	109.5
H18B—C18—H18C	109.5	C25—C26—H26B	109.5
O4—C19—H19A	109.5	H26A—C26—H26B	108.0
O4—C19—H19B	109.5

C21—N1—C1—O1	4.06 (19)	C19—O4—C15—C16	−1.51 (18)
C21—N1—C1—C11	−175.93 (11)	O3—C14—C15—O4	2.05 (17)
O1—C1—C11—C12	−32.62 (17)	C13—C14—C15—O4	178.53 (11)
N1—C1—C11—C12	147.36 (12)	O3—C14—C15—C16	−178.18 (11)
O1—C1—C11—C16	145.07 (13)	C13—C14—C15—C16	−1.70 (18)
N1—C1—C11—C16	−34.94 (17)	O4—C15—C16—C11	178.64 (11)
C16—C11—C12—C13	−0.02 (18)	C14—C15—C16—C11	−1.11 (18)
C1—C11—C12—C13	177.67 (11)	C12—C11—C16—C15	1.99 (18)
C17—O2—C13—C12	0.73 (19)	C1—C11—C16—C15	−175.62 (11)
C17—O2—C13—C14	−179.46 (11)	C1—N1—C21—C26	−150.78 (12)
C11—C12—C13—O2	177.00 (12)	C1—N1—C21—C22	85.85 (16)
C11—C12—C13—C14	−2.81 (19)	N1—C21—C22—C23	179.14 (13)
C18—O3—C14—C15	−108.20 (13)	C26—C21—C22—C23	55.95 (18)
C18—O3—C14—C13	75.33 (15)	C21—C22—C23—C24	−56.00 (19)
O2—C13—C14—O3	0.29 (17)	C22—C23—C24—C25	55.59 (19)
C12—C13—C14—O3	−179.89 (11)	C23—C24—C25—C26	−55.74 (19)
O2—C13—C14—C15	−176.15 (11)	N1—C21—C26—C25	−178.60 (12)
C12—C13—C14—C15	3.68 (19)	C22—C21—C26—C25	−55.27 (17)
C19—O4—C15—C14	178.25 (11)	C24—C25—C26—C21	55.42 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.916 (19)	2.153 (19)	3.0262 (15)	159.0 (15)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₂₃NO₄
M_r	293.35
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	23.4539 (19), 5.2145 (6), 12.4559 (10)
β (°)	92.886 (6)
V (Å³)	1521.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.37 × 0.37 × 0.33

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6868, 2823, 2360
R_int	0.062
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.109, 1.05
No. of reflections	2823
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.22

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), XP (Sheldrick, 2008), PLATON (Spek, 2009) and SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.916 (19)	2.153 (19)	3.0262 (15)	159.0 (15)

Symmetry code: (i) x, y+1, z.

References

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Volume 65| Part 12| December 2009| Page o3234

doi:10.1107/S1600536809050284

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