[5-(2-Fur­yl)-6-nitro-1,2,3,5,6,7-hexa­hydro­imidazo[1,2-a]pyridin-8-yl](phen­yl)methanone

Yaqub, M.; Shafiq, Z.; Qureshi, A.M.; Najam-ul-Haq, M.

doi:10.1107/S1600536809033716

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2283

doi:10.1107/S1600536809033716

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[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-8-yl](phenyl)methanone

Muhammad Yaqub,^a ^* Zahid Shafiq,^a Ashfaq M. Qureshi ^a and Muhammad Najam-ul-Haq ^a

^aDepartment of Chemistry, Bahauddin Zakariya University, Multan 60800, Pakistan
^*Correspondence e-mail: mayaqub2@yahoo.com

(Received 27 July 2009; accepted 24 August 2009; online 29 August 2009)

In the title compound, C₁₈H₁₇N₃O₄, the furyl and phenyl rings are inclined at almost right angles [85.77 (7) and 63.25 (7)°, respectively] to the central imidazo[1,2-a]pyridinyl unit. The structure displays both inter- and intramolecular N—H⋯O hydrogen bonding.

Related literature

For cyclic 1,1-enediamines as intermediates for the construction of heterocyclic compounds, see: Yu et al. (2006 ); Yaqub et al. (2008 ); Wang et al. (1999 ). For related structures, see: Yu et al. (2007 ); Yaqub et al. (2009 ).

Experimental

Crystal data

C₁₈H₁₇N₃O₄
M_r = 339.35
Monoclinic, C 2/c
a = 11.980 (2) Å
b = 15.047 (3) Å
c = 17.932 (4) Å
β = 101.94 (3)°
V = 3162.7 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.45 × 0.33 × 0.32 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.955, T_max = 0.968
5401 measured reflections
2801 independent reflections
2426 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.128
S = 1.14
2801 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4	0.88	2.17	2.714 (2)	119
N1—H1A⋯O4ⁱ	0.88	2.40	3.025 (3)	128
Symmetry code: (i) $[-x, y, -z+{\script{3\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 2001 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809033716/pv2191sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809033716/pv2191Isup2.hkl

checkCIF report

Comment top

The significance of cyclic 1,1-enediamines known as heterocyclic ketene aminals (HKAs) is obvious as a building block in many synthetic operations especially as intermediates for the construction of novel heterocyclic compound (Yaqub et al., 2008; Yu et al., 2006). The condensation through β-carbon and secondary nitrogen with bis-electrophile to form heterocyclic ring is one of the most favorable features of HKAs, (Yaqub et al., 2009; Yu, et al., 2007; Wang et al., 1999) which was utilized to synthesize the title compound (I) by treating nitro derivative of Baylis-Hillman acetates with five membered analogue of heterocyclic ketene aminal. In this paper, we describe the crystal structure of (I).

In the title compound (Fig. 1), the pyridyl ring of the nitroimidazo-pyridinyl moiety adopts a half-chair conformation with C4 lying 0.666 (3) Å out of the plane formed by the atoms N1/N2/C1/C2/C3/C5/C6/C7; N2 showing the maximum deviation of 0.069 (2) Å from this plane. The mean-planes of the furanyl and benzyl rings lie at angles 85.77 (7) and 0.63.25 (7)°, respectively, with respect to the mean-plane formed by the atoms N1/N2/C1/C2/C3/C5/C6/C7 of the nitroimidazo-pyridinyl moiety. The structure is stabilized by both inter- and intra-molecular hydrogen bonding of the type N—H···O (details have been provided in Table 1).

Related literature top

For cyclic 1,1-enediamines as intermediates for the construction of heterocyclic compounds, see: Yu et al. (2006); Yaqub et al. (2008); Wang et al. (1999). For related structures, see: Yu et al. (2007); Yaqub et al. (2009).

Experimental top

Heterocyclic ketene aminal (0.13 g, 0.71 mmol) and (E)-2-nitro-3-(2-furanyl)allylacetate (0.15 g, 0.71 mmol) were stirred in 30 ml of dichloromethane at 273 K for one hour, followed by stirring at room temperature for 6 h (Scheme 2). Solvent was evaporated and residue was passed through short chromatographic column. The elution was carried out by petroleum ether: ethyl acetate (4:1) mixture to get the title compound (I) as a light yellow solid. The single crystals were grown in dichloromethane - petroleum ether (1:5) system at room temperature by slow evaporation. Yield: 75% (0.18 g), m.p. 440–441 K (lit. m. p. 441–442 K) (Yaqub et al., 2008).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2001); cell refinement: RAPID-AUTO (Rigaku, 2001); data reduction: RAPID-AUTO (Rigaku, 2001); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound.
	Fig. 2. The formation of the title compound.

[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin- 8-yl](phenyl)methanone top

Crystal data top

C₁₈H₁₇N₃O₄	F(000) = 1424
M_r = 339.35	D_x = 1.425 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 989 reflections
a = 11.980 (2) Å	θ = 2.2–27.5°
b = 15.047 (3) Å	µ = 0.10 mm⁻¹
c = 17.932 (4) Å	T = 173 K
β = 101.94 (3)°	Block, yellow
V = 3162.7 (11) Å³	0.45 × 0.33 × 0.32 mm
Z = 8

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2801 independent reflections
Radiation source: rotating anode	2426 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans at fixed χ = 45°	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.955, T_max = 0.968	k = −17→17
5401 measured reflections	l = −21→21

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0499P)² + 3.4672P] where P = (F_o² + 2F_c²)/3
2801 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₈H₁₇N₃O₄	V = 3162.7 (11) Å³
M_r = 339.35	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 11.980 (2) Å	µ = 0.10 mm⁻¹
b = 15.047 (3) Å	T = 173 K
c = 17.932 (4) Å	0.45 × 0.33 × 0.32 mm
β = 101.94 (3)°

Data collection top

Rigaku R-AXIS RAPID IP area-detector diffractometer	2801 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2426 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.968	R_int = 0.031
5401 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.14	Δρ_max = 0.37 e Å⁻³
2801 reflections	Δρ_min = −0.36 e Å⁻³
226 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
O1	0.43109 (14)	0.20626 (10)	0.91996 (10)	0.0384 (4)
O2	0.2016 (2)	0.3319 (2)	0.63070 (12)	0.0835 (8)
O3	0.12099 (18)	0.35426 (18)	0.72302 (12)	0.0722 (7)
O4	0.11567 (13)	0.00988 (10)	0.71141 (9)	0.0319 (4)
N1	0.10262 (16)	0.11596 (13)	0.83171 (10)	0.0327 (5)
H1A	0.0780	0.0626	0.8163	0.039*
N2	0.21072 (15)	0.23408 (12)	0.84736 (11)	0.0302 (5)
N3	0.20184 (17)	0.32982 (14)	0.69714 (12)	0.0370 (5)
C1	0.05883 (19)	0.16761 (16)	0.88815 (13)	0.0329 (5)
H1B	0.0652	0.1341	0.9363	0.039*
H1C	−0.0219	0.1844	0.8689	0.039*
C2	0.1352 (2)	0.2487 (2)	0.89931 (15)	0.0473 (7)
H2A	0.0902	0.3038	0.8863	0.057*
H2B	0.1785	0.2527	0.9526	0.057*
C3	0.18456 (17)	0.15910 (14)	0.80613 (12)	0.0244 (5)
C7	0.29353 (18)	0.29889 (14)	0.83329 (13)	0.0280 (5)
H7A	0.2646	0.3596	0.8419	0.034*
C4	0.30665 (18)	0.29262 (15)	0.75038 (13)	0.0289 (5)
H4A	0.3742	0.3290	0.7446	0.035*
C5	0.32660 (18)	0.19731 (14)	0.72796 (13)	0.0286 (5)
H5A	0.3265	0.1949	0.6728	0.034*
H5B	0.4024	0.1773	0.7560	0.034*
C6	0.23556 (17)	0.13503 (14)	0.74538 (12)	0.0247 (5)
C8	0.40885 (18)	0.28698 (14)	0.88525 (12)	0.0254 (5)
C9	0.5402 (2)	0.21114 (16)	0.96169 (14)	0.0359 (6)
H9A	0.5781	0.1644	0.9925	0.043*
C10	0.58593 (19)	0.28997 (15)	0.95339 (13)	0.0312 (5)
H10A	0.6607	0.3094	0.9761	0.037*
C11	0.50011 (19)	0.33953 (15)	0.90356 (13)	0.0318 (5)
H11A	0.5067	0.3987	0.8866	0.038*
C12	0.19701 (17)	0.05876 (14)	0.70164 (12)	0.0240 (5)
C13	0.25482 (18)	0.03347 (13)	0.63770 (12)	0.0243 (5)
C14	0.37074 (19)	0.01371 (15)	0.65132 (14)	0.0327 (5)
H14A	0.4159	0.0210	0.7011	0.039*
C15	0.4210 (2)	−0.01643 (16)	0.59321 (16)	0.0402 (6)
H15A	0.4997	−0.0314	0.6036	0.048*
C16	0.3569 (2)	−0.02476 (15)	0.52020 (15)	0.0396 (6)
H16A	0.3916	−0.0449	0.4802	0.047*
C17	0.2425 (2)	−0.00372 (16)	0.50545 (14)	0.0360 (6)
H17A	0.1987	−0.0080	0.4549	0.043*
C18	0.19096 (19)	0.02370 (14)	0.56414 (13)	0.0296 (5)
H18A	0.1114	0.0359	0.5539	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0377 (9)	0.0257 (8)	0.0469 (11)	−0.0042 (7)	−0.0025 (8)	0.0091 (7)
O2	0.0725 (15)	0.145 (2)	0.0326 (12)	0.0368 (16)	0.0095 (10)	0.0255 (13)
O3	0.0543 (13)	0.109 (2)	0.0460 (13)	0.0391 (13)	−0.0055 (10)	−0.0096 (12)
O4	0.0336 (9)	0.0286 (8)	0.0354 (9)	−0.0075 (7)	0.0116 (7)	−0.0056 (7)
N1	0.0386 (11)	0.0359 (11)	0.0264 (10)	−0.0111 (9)	0.0133 (9)	−0.0063 (8)
N2	0.0266 (10)	0.0309 (10)	0.0345 (11)	−0.0049 (8)	0.0098 (8)	−0.0099 (8)
N3	0.0362 (11)	0.0383 (12)	0.0333 (12)	−0.0004 (9)	−0.0006 (9)	−0.0010 (9)
C1	0.0270 (11)	0.0424 (13)	0.0301 (12)	0.0030 (10)	0.0077 (9)	−0.0023 (10)
C2	0.0517 (16)	0.0595 (18)	0.0352 (15)	−0.0184 (14)	0.0196 (12)	−0.0203 (13)
C3	0.0224 (10)	0.0259 (11)	0.0223 (11)	0.0008 (9)	−0.0013 (8)	−0.0001 (9)
C7	0.0284 (11)	0.0224 (11)	0.0315 (12)	−0.0015 (9)	0.0021 (9)	−0.0052 (9)
C4	0.0260 (11)	0.0277 (12)	0.0309 (12)	−0.0036 (9)	0.0010 (9)	−0.0002 (9)
C5	0.0269 (11)	0.0302 (12)	0.0294 (12)	−0.0043 (9)	0.0069 (9)	−0.0038 (9)
C6	0.0229 (10)	0.0274 (11)	0.0236 (11)	−0.0023 (8)	0.0042 (9)	−0.0018 (9)
C8	0.0313 (12)	0.0212 (10)	0.0239 (11)	0.0008 (9)	0.0064 (9)	−0.0007 (9)
C9	0.0341 (13)	0.0347 (13)	0.0341 (14)	0.0052 (10)	−0.0038 (10)	0.0043 (10)
C10	0.0277 (12)	0.0322 (12)	0.0314 (13)	0.0004 (9)	0.0010 (10)	−0.0056 (10)
C11	0.0330 (12)	0.0226 (11)	0.0373 (13)	−0.0044 (9)	0.0013 (10)	0.0009 (10)
C12	0.0232 (11)	0.0233 (11)	0.0247 (11)	0.0016 (8)	0.0032 (9)	0.0025 (9)
C13	0.0285 (11)	0.0174 (10)	0.0278 (12)	−0.0002 (8)	0.0078 (9)	−0.0013 (8)
C14	0.0286 (12)	0.0327 (12)	0.0360 (13)	0.0024 (10)	0.0049 (10)	0.0049 (10)
C15	0.0364 (13)	0.0335 (13)	0.0562 (17)	0.0082 (11)	0.0226 (13)	0.0089 (12)
C16	0.0561 (16)	0.0248 (12)	0.0469 (16)	0.0038 (11)	0.0316 (13)	−0.0007 (11)
C17	0.0514 (15)	0.0284 (12)	0.0297 (13)	−0.0041 (11)	0.0118 (11)	−0.0044 (10)
C18	0.0314 (12)	0.0253 (11)	0.0313 (13)	0.0001 (9)	0.0048 (10)	−0.0014 (9)

Geometric parameters (Å, º) top

O1—C8	1.366 (3)	C5—C6	1.519 (3)
O1—C9	1.367 (3)	C5—H5A	0.9900
O2—N3	1.191 (3)	C5—H5B	0.9900
O3—N3	1.214 (3)	C6—C12	1.413 (3)
O4—C12	1.262 (3)	C8—C11	1.334 (3)
N1—C3	1.335 (3)	C9—C10	1.328 (3)
N1—C1	1.457 (3)	C9—H9A	0.9500
N1—H1A	0.8800	C10—C11	1.425 (3)
N2—C3	1.350 (3)	C10—H10A	0.9500
N2—C2	1.443 (3)	C11—H11A	0.9500
N2—C7	1.450 (3)	C12—C13	1.506 (3)
N3—C4	1.518 (3)	C13—C18	1.389 (3)
C1—C2	1.513 (3)	C13—C14	1.392 (3)
C1—H1B	0.9900	C14—C15	1.384 (3)
C1—H1C	0.9900	C14—H14A	0.9500
C2—H2A	0.9900	C15—C16	1.380 (4)
C2—H2B	0.9900	C15—H15A	0.9500
C3—C6	1.402 (3)	C16—C17	1.378 (4)
C7—C8	1.509 (3)	C16—H16A	0.9500
C7—C4	1.530 (3)	C17—C18	1.389 (3)
C7—H7A	1.0000	C17—H17A	0.9500
C4—C5	1.522 (3)	C18—H18A	0.9500
C4—H4A	1.0000

C8—O1—C9	106.02 (17)	C6—C5—H5B	109.3
C3—N1—C1	112.05 (19)	C4—C5—H5B	109.3
C3—N1—H1A	124.0	H5A—C5—H5B	108.0
C1—N1—H1A	124.0	C3—C6—C12	119.75 (19)
C3—N2—C2	112.04 (18)	C3—C6—C5	116.57 (19)
C3—N2—C7	123.81 (18)	C12—C6—C5	123.59 (19)
C2—N2—C7	123.56 (19)	C11—C8—O1	110.01 (19)
O2—N3—O3	122.5 (2)	C11—C8—C7	132.9 (2)
O2—N3—C4	117.9 (2)	O1—C8—C7	117.03 (18)
O3—N3—C4	119.5 (2)	C10—C9—O1	110.9 (2)
N1—C1—C2	103.13 (18)	C10—C9—H9A	124.5
N1—C1—H1B	111.1	O1—C9—H9A	124.5
C2—C1—H1B	111.1	C9—C10—C11	106.0 (2)
N1—C1—H1C	111.1	C9—C10—H10A	127.0
C2—C1—H1C	111.1	C11—C10—H10A	127.0
H1B—C1—H1C	109.1	C8—C11—C10	107.0 (2)
N2—C2—C1	103.57 (19)	C8—C11—H11A	126.5
N2—C2—H2A	111.0	C10—C11—H11A	126.5
C1—C2—H2A	111.0	O4—C12—C6	124.7 (2)
N2—C2—H2B	111.0	O4—C12—C13	116.65 (18)
C1—C2—H2B	111.0	C6—C12—C13	118.62 (18)
H2A—C2—H2B	109.0	C18—C13—C14	118.5 (2)
N1—C3—N2	108.79 (19)	C18—C13—C12	120.01 (19)
N1—C3—C6	127.7 (2)	C14—C13—C12	121.3 (2)
N2—C3—C6	123.53 (19)	C15—C14—C13	120.8 (2)
N2—C7—C8	112.63 (18)	C15—C14—H14A	119.6
N2—C7—C4	109.83 (17)	C13—C14—H14A	119.6
C8—C7—C4	109.13 (18)	C16—C15—C14	120.1 (2)
N2—C7—H7A	108.4	C16—C15—H15A	120.0
C8—C7—H7A	108.4	C14—C15—H15A	120.0
C4—C7—H7A	108.4	C17—C16—C15	119.8 (2)
N3—C4—C5	109.63 (18)	C17—C16—H16A	120.1
N3—C4—C7	110.51 (18)	C15—C16—H16A	120.1
C5—C4—C7	111.60 (18)	C16—C17—C18	120.2 (2)
N3—C4—H4A	108.3	C16—C17—H17A	119.9
C5—C4—H4A	108.3	C18—C17—H17A	119.9
C7—C4—H4A	108.3	C17—C18—C13	120.5 (2)
C6—C5—C4	111.62 (18)	C17—C18—H18A	119.8
C6—C5—H5A	109.3	C13—C18—H18A	119.8
C4—C5—H5A	109.3

C3—N1—C1—C2	−4.9 (3)	C4—C5—C6—C12	148.1 (2)
C3—N2—C2—C1	3.0 (3)	C9—O1—C8—C11	0.8 (3)
C7—N2—C2—C1	174.5 (2)	C9—O1—C8—C7	178.42 (19)
N1—C1—C2—N2	1.0 (3)	N2—C7—C8—C11	−163.8 (2)
C1—N1—C3—N2	6.9 (3)	C4—C7—C8—C11	74.0 (3)
C1—N1—C3—C6	−171.3 (2)	N2—C7—C8—O1	19.2 (3)
C2—N2—C3—N1	−6.2 (3)	C4—C7—C8—O1	−103.0 (2)
C7—N2—C3—N1	−177.64 (19)	C8—O1—C9—C10	−0.9 (3)
C2—N2—C3—C6	172.1 (2)	O1—C9—C10—C11	0.6 (3)
C7—N2—C3—C6	0.7 (3)	O1—C8—C11—C10	−0.4 (3)
C3—N2—C7—C8	−97.8 (2)	C7—C8—C11—C10	−177.5 (2)
C2—N2—C7—C8	91.7 (3)	C9—C10—C11—C8	−0.1 (3)
C3—N2—C7—C4	24.0 (3)	C3—C6—C12—O4	2.1 (3)
C2—N2—C7—C4	−146.4 (2)	C5—C6—C12—O4	−174.3 (2)
O2—N3—C4—C5	−58.9 (3)	C3—C6—C12—C13	−178.84 (19)
O3—N3—C4—C5	119.4 (3)	C5—C6—C12—C13	4.7 (3)
O2—N3—C4—C7	177.6 (2)	O4—C12—C13—C18	55.0 (3)
O3—N3—C4—C7	−4.0 (3)	C6—C12—C13—C18	−124.1 (2)
N2—C7—C4—N3	72.3 (2)	O4—C12—C13—C14	−120.7 (2)
C8—C7—C4—N3	−163.80 (17)	C6—C12—C13—C14	60.2 (3)
N2—C7—C4—C5	−50.0 (2)	C18—C13—C14—C15	−1.1 (3)
C8—C7—C4—C5	73.9 (2)	C12—C13—C14—C15	174.7 (2)
N3—C4—C5—C6	−69.8 (2)	C13—C14—C15—C16	1.9 (4)
C7—C4—C5—C6	53.0 (2)	C14—C15—C16—C17	−0.6 (4)
N1—C3—C6—C12	2.7 (3)	C15—C16—C17—C18	−1.6 (4)
N2—C3—C6—C12	−175.3 (2)	C16—C17—C18—C13	2.5 (3)
N1—C3—C6—C5	179.4 (2)	C14—C13—C18—C17	−1.1 (3)
N2—C3—C6—C5	1.4 (3)	C12—C13—C18—C17	−176.9 (2)
C4—C5—C6—C3	−28.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.88	2.17	2.714 (2)	119
N1—H1A···O4ⁱ	0.88	2.40	3.025 (3)	128

Symmetry code: (i) −x, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₃O₄
M_r	339.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	11.980 (2), 15.047 (3), 17.932 (4)
β (°)	101.94 (3)
V (Å³)	3162.7 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.33 × 0.32

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP area-detector diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.955, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	5401, 2801, 2426
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.128, 1.14
No. of reflections	2801
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.36

Computer programs: RAPID-AUTO (Rigaku, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4	0.88	2.17	2.714 (2)	119.2
N1—H1A···O4ⁱ	0.88	2.40	3.025 (3)	127.8

Symmetry code: (i) −x, y, −z+3/2.

Acknowledgements

We thank the Institute of Chemistry Chinese Academy of Science, Beijing, China for providing X-ray single-crystal facilities and the Higher Education Commission, Islamabad, Pakistan for providing financial support.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (2001). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, M.-X., Miao, W.-S., Cheng, Y. & Huang, Z.-T. (1999). Tetrahedron, 55, 14611–14622. Web of Science CrossRef CAS Google Scholar
Yaqub, M., Shafiq, Z., Qureshi, A. M. & Najam-ul-Haq, M. (2009). Acta Cryst. E65, o1869. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yaqub, M., Yu, C.-Y., Jia, Y.-M. & Huang, Z.-T. (2008). Synlett, pp. 1357–1360. Google Scholar
Yu, C.-Y., Yang, P.-H., Zhao, M.-X. & Huang, Z.-T. (2006). Synlett, pp. 1835–1840. Web of Science CrossRef Google Scholar
Yu, C.-Y., Yuan, X.-N. & Huang, Z.-T. (2007). Acta Cryst. E63, o3186. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 9| September 2009| Page o2283

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

[5-(2-Fur­yl)-6-nitro-1,2,3,5,6,7-hexa­hydro­imidazo[1,2-a]pyridin-8-yl](phen­yl)methanone

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

[5-(2-Furyl)-6-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-8-yl](phenyl)methanone