Literature DB >> 26870561

Crystal structure of 2-(4-meth-oxy-phen-yl)-6-nitro-imidazo[1,2-a]pyridine-3-carbaldehyde.

Mohamed Koudad¹, Abdelmalik Elaatiaoui¹, Noureddine Benchat², Mohamed Saadi³, Lahcen El Ammari³.

Abstract

In the title compound, C15H11N3O4, the imidazo[1,2-a] pyridine ring system is almost planar [r.m.s. deviation = 0.028 (2) Å]. Its mean plane makes dihedral angles of 33.92 (7) and 34.56 (6)° with the meth-oxy-phenyl ring and the nitro group, respectively. The cohesion of the crystal structure is ensured by C-H⋯N and C-H⋯O hydrogen bonds, forming layers almost parallel to the ac plane.

Entities: Chemical Disease Species

Keywords: carbaldehyde; crystal structure; hydrogen bonding; imidazo[1,2-a]pyridine

Year: 2015 PMID： 26870561 PMCID： PMC4719933 DOI： 10.1107/S2056989015021957

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For biological activities of derivatives of the title compound, see: Rupert et al. (2003 ▸); Hranjec et al. (2007 ▸); Hamdouchi et al. (1999 ▸); Rival et al. (1992 ▸); Scribner et al. (2008 ▸); Bode et al. (2011 ▸). For the synthesis of similar compounds, see: Sumalatha et al. (2009 ▸); Elaatiaoui et al. (2014 ▸, 2015 ▸).

Experimental

Crystal data

C15H11N3O4 M = 297.27 Monoclinic, a = 10.8516 (6) Å b = 12.0710 (6) Å c = 10.2631 (5) Å β = 93.200 (2)° V = 1342.26 (12) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 296 K 0.42 × 0.31 × 0.26 mm

Data collection

Bruker X8 APEX diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.673, T max = 0.746 25892 measured reflections 3472 independent reflections 2139 reflections with I > 2σ(I) R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.120 S = 1.02 3472 reflections 200 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸). Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015021957/su5244sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015021957/su5244Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015021957/su5244Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015021957/su5244fig1.tif A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. Click here for additional data file. . DOI: 10.1107/S2056989015021957/su5244fig2.tif A partial view of the crystal packing of the title compound, showing molecules linked by hydrogen bonds (dashed lines; Table 1), forming layers parallel to (101). CCDC reference: 1437519 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₅H₁₁N₃O₄	F(000) = 616
M_r = 297.27	D_x = 1.471 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8516 (6) Å	Cell parameters from 3472 reflections
b = 12.0710 (6) Å	θ = 2.5–28.7°
c = 10.2631 (5) Å	µ = 0.11 mm⁻¹
β = 93.200 (2)°	T = 296 K
V = 1342.26 (12) Å³	Block, colourless
Z = 4	0.42 × 0.31 × 0.26 mm

Bruker X8 APEX diffractometer	3472 independent reflections
Radiation source: fine-focus sealed tube	2139 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 28.7°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
T_min = 0.673, T_max = 0.746	k = −16→16
25892 measured reflections	l = −13→10

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.044	w = 1/[σ²(F_o²) + (0.0468P)² + 0.3011P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.120	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.21 e Å⁻³
3472 reflections	Δρ_min = −0.16 e Å⁻³
200 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0038 (11)

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.

	x	y	z	U_iso*/U_eq
C1	−0.02574 (15)	0.14080 (13)	0.14955 (15)	0.0384 (4)
H1	−0.0116	0.0650	0.1559	0.046*
C2	−0.11433 (16)	0.19026 (13)	0.21703 (15)	0.0396 (4)
C3	−0.13789 (17)	0.30501 (14)	0.21067 (18)	0.0479 (4)
H3	−0.1979	0.3366	0.2601	0.057*
C4	−0.07141 (17)	0.36854 (14)	0.13112 (18)	0.0479 (4)
H4	−0.0867	0.4442	0.1242	0.058*
C5	0.02062 (16)	0.31952 (12)	0.05933 (16)	0.0397 (4)
C6	0.14059 (15)	0.18113 (12)	−0.00409 (15)	0.0369 (4)
C7	0.20276 (17)	0.07630 (13)	0.00131 (16)	0.0423 (4)
H7	0.2746	0.0694	−0.0433	0.051*
C8	0.17220 (16)	0.28204 (13)	−0.05971 (15)	0.0377 (4)
C9	0.27357 (16)	0.30700 (13)	−0.14343 (15)	0.0389 (4)
C10	0.33469 (18)	0.40926 (14)	−0.12918 (18)	0.0490 (5)
H10	0.3104	0.4595	−0.0668	0.059*
C11	0.42963 (19)	0.43593 (15)	−0.20600 (19)	0.0547 (5)
H11	0.4698	0.5036	−0.1945	0.066*
C12	0.46660 (17)	0.36275 (15)	−0.30113 (17)	0.0467 (4)
C13	0.40815 (17)	0.26118 (14)	−0.31569 (16)	0.0435 (4)
H13	0.4330	0.2111	−0.3779	0.052*
C14	0.31262 (17)	0.23437 (13)	−0.23732 (16)	0.0422 (4)
H14	0.2738	0.1660	−0.2479	0.051*
C15	0.5928 (2)	0.32902 (19)	−0.4794 (2)	0.0685 (6)
H15A	0.6582	0.3633	−0.5241	0.103*
H15B	0.6204	0.2588	−0.4449	0.103*
H15C	0.5228	0.3180	−0.5394	0.103*
N1	−0.18828 (14)	0.11943 (13)	0.29732 (14)	0.0482 (4)
N2	0.04176 (12)	0.20585 (10)	0.07215 (12)	0.0356 (3)
N3	0.09779 (14)	0.36523 (11)	−0.02137 (14)	0.0438 (4)
O1	−0.17708 (14)	0.01936 (11)	0.28788 (14)	0.0623 (4)
O2	−0.25834 (15)	0.16393 (13)	0.37021 (15)	0.0741 (5)
O3	0.16791 (13)	−0.00450 (9)	0.06039 (13)	0.0548 (4)
O4	0.55866 (13)	0.39871 (12)	−0.37535 (13)	0.0631 (4)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0429 (9)	0.0298 (7)	0.0421 (9)	−0.0019 (7)	−0.0011 (8)	0.0014 (7)
C2	0.0425 (10)	0.0377 (8)	0.0385 (9)	−0.0045 (7)	0.0019 (8)	−0.0010 (7)
C3	0.0515 (11)	0.0395 (9)	0.0532 (11)	0.0025 (8)	0.0086 (9)	−0.0072 (8)
C4	0.0546 (11)	0.0304 (8)	0.0594 (11)	0.0055 (8)	0.0083 (9)	−0.0021 (8)
C5	0.0467 (10)	0.0270 (7)	0.0448 (9)	0.0014 (7)	−0.0011 (8)	0.0011 (7)
C6	0.0396 (9)	0.0325 (8)	0.0385 (8)	−0.0008 (7)	0.0011 (7)	−0.0006 (7)
C7	0.0463 (10)	0.0350 (8)	0.0456 (10)	0.0034 (7)	0.0036 (8)	0.0010 (7)
C8	0.0432 (9)	0.0326 (8)	0.0370 (8)	0.0001 (7)	−0.0026 (7)	0.0012 (6)
C9	0.0436 (9)	0.0351 (8)	0.0378 (9)	−0.0004 (7)	−0.0009 (7)	0.0040 (7)
C10	0.0588 (12)	0.0380 (9)	0.0506 (10)	−0.0050 (8)	0.0070 (9)	−0.0049 (8)
C11	0.0641 (13)	0.0406 (9)	0.0603 (12)	−0.0170 (9)	0.0103 (10)	−0.0053 (8)
C12	0.0479 (10)	0.0484 (10)	0.0441 (10)	−0.0087 (8)	0.0035 (8)	0.0026 (8)
C13	0.0490 (11)	0.0428 (9)	0.0386 (9)	−0.0031 (8)	0.0015 (8)	−0.0022 (7)
C14	0.0504 (11)	0.0342 (8)	0.0418 (9)	−0.0074 (7)	−0.0004 (8)	0.0010 (7)
C15	0.0619 (14)	0.0834 (16)	0.0622 (13)	−0.0196 (12)	0.0228 (11)	−0.0136 (11)
N1	0.0485 (9)	0.0496 (9)	0.0465 (8)	−0.0048 (7)	0.0042 (7)	0.0000 (7)
N2	0.0399 (8)	0.0277 (6)	0.0388 (7)	0.0004 (5)	−0.0002 (6)	0.0000 (5)
N3	0.0514 (9)	0.0316 (7)	0.0487 (8)	0.0017 (6)	0.0044 (7)	0.0039 (6)
O1	0.0686 (10)	0.0432 (7)	0.0765 (10)	−0.0044 (6)	0.0153 (8)	0.0124 (7)
O2	0.0803 (11)	0.0707 (10)	0.0752 (10)	−0.0053 (8)	0.0386 (9)	−0.0078 (8)
O3	0.0638 (9)	0.0343 (6)	0.0676 (8)	0.0080 (6)	0.0155 (7)	0.0104 (6)
O4	0.0654 (9)	0.0664 (9)	0.0593 (8)	−0.0241 (7)	0.0201 (7)	−0.0072 (7)

C1—C2	1.354 (2)	C9—C14	1.386 (2)
C1—N2	1.360 (2)	C9—C10	1.405 (2)
C1—H1	0.9300	C10—C11	1.370 (3)
C2—C3	1.409 (2)	C10—H10	0.9300
C2—N1	1.459 (2)	C11—C12	1.392 (3)
C3—C4	1.357 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—O4	1.361 (2)
C4—C5	1.405 (2)	C12—C13	1.385 (2)
C4—H4	0.9300	C13—C14	1.385 (2)
C5—N3	1.330 (2)	C13—H13	0.9300
C5—N2	1.3961 (19)	C14—H14	0.9300
C6—N2	1.395 (2)	C15—O4	1.424 (2)
C6—C8	1.396 (2)	C15—H15A	0.9600
C6—C7	1.434 (2)	C15—H15B	0.9600
C7—O3	1.2197 (19)	C15—H15C	0.9600
C7—H7	0.9300	N1—O1	1.2184 (19)
C8—N3	1.360 (2)	N1—O2	1.220 (2)
C8—C9	1.464 (2)

C2—C1—N2	117.71 (14)	C11—C10—H10	119.6
C2—C1—H1	121.1	C9—C10—H10	119.6
N2—C1—H1	121.1	C10—C11—C12	120.65 (17)
C1—C2—C3	122.79 (16)	C10—C11—H11	119.7
C1—C2—N1	117.32 (15)	C12—C11—H11	119.7
C3—C2—N1	119.88 (16)	O4—C12—C13	124.62 (17)
C4—C3—C2	118.83 (16)	O4—C12—C11	116.07 (16)
C4—C3—H3	120.6	C13—C12—C11	119.30 (17)
C2—C3—H3	120.6	C12—C13—C14	119.81 (16)
C3—C4—C5	119.67 (16)	C12—C13—H13	120.1
C3—C4—H4	120.2	C14—C13—H13	120.1
C5—C4—H4	120.2	C13—C14—C9	121.56 (15)
N3—C5—N2	111.14 (14)	C13—C14—H14	119.2
N3—C5—C4	129.99 (15)	C9—C14—H14	119.2
N2—C5—C4	118.85 (15)	O4—C15—H15A	109.5
N2—C6—C8	104.88 (13)	O4—C15—H15B	109.5
N2—C6—C7	122.83 (14)	H15A—C15—H15B	109.5
C8—C6—C7	131.31 (16)	O4—C15—H15C	109.5
O3—C7—C6	124.53 (17)	H15A—C15—H15C	109.5
O3—C7—H7	117.7	H15B—C15—H15C	109.5
C6—C7—H7	117.7	O1—N1—O2	123.60 (16)
N3—C8—C6	111.25 (15)	O1—N1—C2	118.41 (15)
N3—C8—C9	119.68 (14)	O2—N1—C2	118.00 (15)
C6—C8—C9	128.98 (15)	C1—N2—C6	131.33 (13)
C14—C9—C10	117.84 (16)	C1—N2—C5	122.11 (14)
C14—C9—C8	123.12 (15)	C6—N2—C5	106.55 (13)
C10—C9—C8	119.04 (15)	C5—N3—C8	106.16 (13)
C11—C10—C9	120.81 (17)	C12—O4—C15	117.45 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N3ⁱ	0.93	2.53	3.412 (2)	158
C15—H15A···O3ⁱⁱ	0.96	2.52	3.423 (2)	158
C14—H14···O1ⁱⁱⁱ	0.93	2.50	3.425 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N3ⁱ	0.93	2.53	3.412 (2)	158
C15—H15A⋯O3ⁱⁱ	0.96	2.52	3.423 (2)	158
C14—H14⋯O1ⁱⁱⁱ	0.93	2.50	3.425 (2)	177

Symmetry codes: (i) ; (ii) ; (iii) .

9 in total

1. Synthesis and antibacterial activity of some imidazo[1,2-a]pyrimidine derivatives.

Authors: Y Rival; G Grassy; G Michel
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2. Synthesis and biological activity of imidazopyridine anticoccidial agents: Part II.

Authors: Andrew Scribner; Richard Dennis; Shuliang Lee; Gilles Ouvry; David Perrey; Michael Fisher; Matthew Wyvratt; Penny Leavitt; Paul Liberator; Anne Gurnett; Chris Brown; John Mathew; Donald Thompson; Dennis Schmatz; Tesfaye Biftu
Journal: Eur J Med Chem Date: 2007-09-26 Impact factor: 6.514

3. A short history of SHELX.

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4. 2-Amino-3-substituted-6-[(E)-1-phenyl-2-(N-methylcarbamoyl)vinyl]imid azo[1,2-a]pyridines as a novel class of inhibitors of human rhinovirus: stereospecific synthesis and antiviral activity.

Authors: C Hamdouchi; J de Blas; M del Prado; J Gruber; B A Heinz; L Vance
Journal: J Med Chem Date: 1999-01-14 Impact factor: 7.446

5. Imidazopyrimidines, potent inhibitors of p38 MAP kinase.

Authors: Kenneth C Rupert; James R Henry; John H Dodd; Scott A Wadsworth; Druie E Cavender; Gilbert C Olini; Bohumila Fahmy; John J Siekierka
Journal: Bioorg Med Chem Lett Date: 2003-02-10 Impact factor: 2.823

6. Novel cyano- and amidino-substituted derivatives of styryl-2-benzimidazoles and benzimidazo[1,2-a]quinolines. Synthesis, photochemical synthesis, DNA binding, and antitumor evaluation, part 3.

Authors: Marijana Hranjec; Marijeta Kralj; Ivo Piantanida; Mirela Sedić; Lidija Suman; Kresimir Pavelić; Grace Karminski-Zamola
Journal: J Med Chem Date: 2007-10-13 Impact factor: 7.446

1 in total

1. Crystal Correlation Of Heterocyclic Imidazo[1,2-a]pyridine Analogues and Their Anticholinesterase Potential Evaluation.

Authors: Huey Chong Kwong; C S Chidan Kumar; Siau Hui Mah; Yew Leng Mah; Tze Shyang Chia; Ching Kheng Quah; Gin Keat Lim; Siddegowda Chandraju
Journal: Sci Rep Date: 2019-01-30 Impact factor: 4.379