Literature DB >> 22904934

3-(1H-1,3-Benzimidazol-2-yl)-2,7-dimeth-oxy-quinoline.

Hayette Alliouche, Sofiane Bouacida, Thierry Roisnel, Ali Belfaitah.

Abstract

In the title mol-ecule, C(18)H(15)N(3)O(2), the dihedral angle between the quinoline and benzimidazole ring systems is 23.57 (5)°. The C atoms of the meth-oxy groups are both close to being coplanar with their attached ring systems [deviations = 0.193 (2) and -0.020 (2) Å]. An intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into C(4) chains propagating in [010]. Weak C-H⋯π inter-actions also occur.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 22904934 PMCID： PMC3414947 DOI： 10.1107/S1600536812032357

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For our previous work on the preparation of functionalized heterocyclic compounds with potential biological activity, see: Benzerka et al. (2012 ▶); Hayour et al. (2011 ▶). For further synthetic details, see: Fioraventi et al. (2006 ▶).

Experimental

Crystal data

C18H15N3O2 M = 305.33 Orthorhombic, a = 6.7094 (2) Å b = 9.4134 (3) Å c = 49.1620 (16) Å V = 3104.99 (17) Å3 Z = 8 Mo Kα radiation μ = 0.09 mm−1 T = 150 K 0.51 × 0.29 × 0.09 mm

Data collection

Bruker APEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.900, T max = 0.992 14322 measured reflections 3398 independent reflections 2696 reflections with I > 2σ(I) R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.112 S = 1.03 3398 reflections 210 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032357/hb6897sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032357/hb6897Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812032357/hb6897Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₈H₁₅N₃O₂	F(000) = 1280
M_r = 305.33	D_x = 1.306 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3402 reflections
a = 6.7094 (2) Å	θ = 3.2–26.7°
b = 9.4134 (3) Å	µ = 0.09 mm⁻¹
c = 49.1620 (16) Å	T = 150 K
V = 3104.99 (17) Å³	Block, colourless
Z = 8	0.51 × 0.29 × 0.09 mm

Bruker APEXII diffractometer	2696 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
CCD rotation images, thin slices scans	θ_max = 27.1°, θ_min = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
T_min = 0.900, T_max = 0.992	k = −12→11
14322 measured reflections	l = −51→62
3398 independent reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0451P)² + 1.4136P] where P = (F_o² + 2F_c²)/3
3398 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
C1	1.2836 (2)	0.46202 (18)	0.63727 (4)	0.0326 (4)
H1A	1.272	0.4041	0.6208	0.049*
H1B	1.3178	0.4009	0.6527	0.049*
H1C	1.3884	0.5334	0.6347	0.049*
C3	1.0281 (2)	0.62110 (15)	0.62327 (3)	0.0232 (3)
C5	1.0569 (2)	0.73868 (16)	0.58254 (3)	0.0258 (3)
C6	1.1711 (3)	0.76468 (17)	0.55888 (3)	0.0301 (4)
H6	1.2896	0.7122	0.5555	0.036*
C7	1.1086 (3)	0.86695 (19)	0.54070 (3)	0.0329 (4)
C9	1.3846 (3)	0.8225 (2)	0.51100 (4)	0.0453 (5)
H9A	1.4838	0.8368	0.5254	0.068*
H9B	1.4391	0.855	0.4936	0.068*
H9C	1.3514	0.7213	0.5098	0.068*
C10	0.9307 (3)	0.94447 (19)	0.54508 (3)	0.0357 (4)
H10	0.8893	1.0141	0.5323	0.043*
C11	0.8182 (3)	0.91890 (18)	0.56783 (3)	0.0335 (4)
H11	0.6987	0.9709	0.5707	0.04*
C12	0.8784 (2)	0.81534 (16)	0.58716 (3)	0.0270 (3)
C13	0.7714 (2)	0.78642 (16)	0.61140 (3)	0.0264 (3)
H13	0.6494	0.8344	0.6149	0.032*
C14	0.8429 (2)	0.68943 (15)	0.62988 (3)	0.0231 (3)
C15	0.7363 (2)	0.66229 (15)	0.65547 (3)	0.0219 (3)
C18	0.5356 (2)	0.68915 (15)	0.68937 (3)	0.0239 (3)
C19	0.3995 (3)	0.73837 (17)	0.70884 (3)	0.0310 (4)
H19	0.3424	0.8305	0.7075	0.037*
C20	0.3513 (3)	0.64821 (18)	0.73003 (3)	0.0327 (4)
H20	0.259	0.6788	0.7435	0.039*
C21	0.4363 (3)	0.51183 (18)	0.73215 (3)	0.0307 (4)
H21	0.3998	0.4528	0.747	0.037*
C22	0.5711 (2)	0.46135 (16)	0.71324 (3)	0.0266 (3)
H22	0.6275	0.3691	0.7147	0.032*
C23	0.6202 (2)	0.55309 (15)	0.69194 (3)	0.0225 (3)
N4	1.12891 (19)	0.64018 (13)	0.60072 (3)	0.0254 (3)
N16	0.74790 (19)	0.53920 (13)	0.67005 (2)	0.0229 (3)
H16	0.8226	0.465	0.6662	0.027*
N17	0.6102 (2)	0.75567 (13)	0.66624 (3)	0.0253 (3)
O2	1.09768 (16)	0.53168 (11)	0.64249 (2)	0.0285 (3)
O8	1.2084 (2)	0.90194 (14)	0.51729 (2)	0.0424 (3)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0285 (9)	0.0335 (9)	0.0357 (9)	0.0116 (7)	0.0000 (7)	0.0024 (7)
C3	0.0269 (8)	0.0181 (7)	0.0247 (8)	−0.0009 (6)	−0.0013 (7)	−0.0007 (6)
C5	0.0301 (8)	0.0239 (7)	0.0234 (8)	−0.0010 (6)	−0.0007 (7)	−0.0015 (6)
C6	0.0320 (8)	0.0325 (9)	0.0257 (8)	0.0016 (7)	0.0022 (7)	−0.0016 (7)
C7	0.0396 (10)	0.0378 (9)	0.0213 (8)	−0.0032 (8)	0.0024 (7)	0.0019 (7)
C9	0.0401 (10)	0.0612 (13)	0.0344 (10)	0.0042 (9)	0.0114 (9)	0.0084 (9)
C10	0.0455 (10)	0.0363 (9)	0.0254 (9)	0.0032 (8)	−0.0019 (8)	0.0065 (7)
C11	0.0373 (9)	0.0348 (9)	0.0285 (9)	0.0071 (8)	−0.0002 (8)	0.0043 (7)
C12	0.0322 (8)	0.0244 (8)	0.0245 (8)	−0.0002 (7)	−0.0010 (7)	0.0001 (6)
C13	0.0277 (8)	0.0229 (7)	0.0285 (8)	0.0029 (6)	0.0007 (7)	−0.0006 (6)
C14	0.0250 (8)	0.0178 (7)	0.0265 (8)	−0.0023 (6)	0.0016 (7)	−0.0019 (6)
C15	0.0240 (7)	0.0170 (7)	0.0247 (7)	−0.0018 (6)	−0.0006 (6)	−0.0001 (6)
C18	0.0260 (8)	0.0195 (7)	0.0261 (8)	−0.0023 (6)	0.0019 (7)	−0.0006 (6)
C19	0.0319 (9)	0.0262 (8)	0.0350 (9)	0.0014 (7)	0.0063 (8)	−0.0037 (7)
C20	0.0313 (9)	0.0364 (9)	0.0303 (9)	−0.0031 (7)	0.0085 (7)	−0.0052 (7)
C21	0.0347 (9)	0.0325 (8)	0.0250 (8)	−0.0091 (7)	0.0020 (7)	0.0002 (7)
C22	0.0297 (8)	0.0233 (7)	0.0269 (8)	−0.0029 (6)	−0.0022 (7)	0.0015 (6)
C23	0.0232 (7)	0.0204 (7)	0.0239 (8)	−0.0036 (6)	−0.0002 (6)	−0.0024 (6)
N4	0.0271 (7)	0.0239 (6)	0.0251 (7)	−0.0003 (5)	0.0009 (6)	0.0005 (5)
N16	0.0256 (6)	0.0184 (6)	0.0246 (7)	0.0026 (5)	0.0018 (6)	0.0011 (5)
N17	0.0273 (7)	0.0195 (6)	0.0291 (7)	−0.0002 (5)	0.0049 (6)	0.0009 (5)
O2	0.0280 (6)	0.0260 (6)	0.0317 (6)	0.0061 (5)	0.0031 (5)	0.0067 (5)
O8	0.0475 (8)	0.0515 (8)	0.0282 (7)	0.0046 (6)	0.0086 (6)	0.0112 (6)

C1—O2	1.4327 (19)	C11—H11	0.95
C1—H1A	0.98	C12—C13	1.418 (2)
C1—H1B	0.98	C13—C14	1.375 (2)
C1—H1C	0.98	C13—H13	0.95
C3—N4	1.311 (2)	C14—C15	1.470 (2)
C3—O2	1.3490 (18)	C15—N17	1.3297 (19)
C3—C14	1.436 (2)	C15—N16	1.3646 (18)
C5—N4	1.376 (2)	C18—N17	1.3912 (19)
C5—C6	1.414 (2)	C18—C19	1.402 (2)
C5—C12	1.416 (2)	C18—C23	1.407 (2)
C6—C7	1.379 (2)	C19—C20	1.382 (2)
C6—H6	0.95	C19—H19	0.95
C7—O8	1.372 (2)	C20—C21	1.409 (2)
C7—C10	1.416 (3)	C20—H20	0.95
C9—O8	1.433 (2)	C21—C22	1.381 (2)
C9—H9A	0.98	C21—H21	0.95
C9—H9B	0.98	C22—C23	1.397 (2)
C9—H9C	0.98	C22—H22	0.95
C10—C11	1.371 (2)	C23—N16	1.3817 (19)
C10—H10	0.95	N16—H16	0.88
C11—C12	1.420 (2)

O2—C1—H1A	109.5	C14—C13—H13	119.8
O2—C1—H1B	109.5	C12—C13—H13	119.8
H1A—C1—H1B	109.5	C13—C14—C3	116.74 (14)
O2—C1—H1C	109.5	C13—C14—C15	120.74 (14)
H1A—C1—H1C	109.5	C3—C14—C15	122.49 (13)
H1B—C1—H1C	109.5	N17—C15—N16	112.88 (13)
N4—C3—O2	119.97 (14)	N17—C15—C14	122.37 (13)
N4—C3—C14	125.19 (14)	N16—C15—C14	124.70 (13)
O2—C3—C14	114.84 (13)	N17—C18—C19	130.07 (14)
N4—C5—C6	117.44 (14)	N17—C18—C23	109.77 (13)
N4—C5—C12	122.40 (14)	C19—C18—C23	120.15 (14)
C6—C5—C12	120.13 (14)	C20—C19—C18	117.66 (15)
C7—C6—C5	119.29 (16)	C20—C19—H19	121.2
C7—C6—H6	120.4	C18—C19—H19	121.2
C5—C6—H6	120.4	C19—C20—C21	121.37 (16)
O8—C7—C6	124.28 (16)	C19—C20—H20	119.3
O8—C7—C10	114.55 (15)	C21—C20—H20	119.3
C6—C7—C10	121.17 (16)	C22—C21—C20	121.94 (15)
O8—C9—H9A	109.5	C22—C21—H21	119
O8—C9—H9B	109.5	C20—C21—H21	119
H9A—C9—H9B	109.5	C21—C22—C23	116.50 (15)
O8—C9—H9C	109.5	C21—C22—H22	121.7
H9A—C9—H9C	109.5	C23—C22—H22	121.7
H9B—C9—H9C	109.5	N16—C23—C22	132.20 (14)
C11—C10—C7	119.87 (16)	N16—C23—C18	105.44 (13)
C11—C10—H10	120.1	C22—C23—C18	122.36 (14)
C7—C10—H10	120.1	C3—N4—C5	117.44 (13)
C10—C11—C12	120.65 (16)	C15—N16—C23	107.05 (12)
C10—C11—H11	119.7	C15—N16—H16	126.5
C12—C11—H11	119.7	C23—N16—H16	126.5
C5—C12—C13	117.74 (14)	C15—N17—C18	104.86 (12)
C5—C12—C11	118.88 (15)	C3—O2—C1	117.47 (12)
C13—C12—C11	123.36 (15)	C7—O8—C9	117.27 (14)
C14—C13—C12	120.40 (14)

N4—C5—C6—C7	−177.24 (15)	C23—C18—C19—C20	−0.8 (2)
C12—C5—C6—C7	1.1 (2)	C18—C19—C20—C21	0.3 (3)
C5—C6—C7—O8	179.35 (15)	C19—C20—C21—C22	−0.1 (3)
C5—C6—C7—C10	−1.1 (3)	C20—C21—C22—C23	0.4 (2)
O8—C7—C10—C11	−179.94 (16)	C21—C22—C23—N16	179.34 (16)
C6—C7—C10—C11	0.5 (3)	C21—C22—C23—C18	−1.0 (2)
C7—C10—C11—C12	0.1 (3)	N17—C18—C23—N16	0.35 (17)
N4—C5—C12—C13	−0.8 (2)	C19—C18—C23—N16	−179.03 (14)
C6—C5—C12—C13	−179.12 (14)	N17—C18—C23—C22	−179.41 (14)
N4—C5—C12—C11	177.74 (15)	C19—C18—C23—C22	1.2 (2)
C6—C5—C12—C11	−0.6 (2)	O2—C3—N4—C5	−176.33 (13)
C10—C11—C12—C5	−0.1 (3)	C14—C3—N4—C5	3.4 (2)
C10—C11—C12—C13	178.40 (16)	C6—C5—N4—C3	176.76 (14)
C5—C12—C13—C14	1.5 (2)	C12—C5—N4—C3	−1.6 (2)
C11—C12—C13—C14	−176.94 (15)	N17—C15—N16—C23	−0.02 (17)
C12—C13—C14—C3	0.0 (2)	C14—C15—N16—C23	−177.42 (14)
C12—C13—C14—C15	177.97 (14)	C22—C23—N16—C15	179.52 (16)
N4—C3—C14—C13	−2.7 (2)	C18—C23—N16—C15	−0.20 (16)
O2—C3—C14—C13	177.08 (13)	N16—C15—N17—C18	0.23 (17)
N4—C3—C14—C15	179.41 (14)	C14—C15—N17—C18	177.70 (14)
O2—C3—C14—C15	−0.8 (2)	C19—C18—N17—C15	178.94 (17)
C13—C14—C15—N17	−22.2 (2)	C23—C18—N17—C15	−0.36 (17)
C3—C14—C15—N17	155.59 (15)	N4—C3—O2—C1	0.8 (2)
C13—C14—C15—N16	154.92 (15)	C14—C3—O2—C1	−179.00 (13)
C3—C14—C15—N16	−27.2 (2)	C6—C7—O8—C9	2.5 (3)
N17—C18—C19—C20	179.94 (16)	C10—C7—O8—C9	−177.05 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16···N17ⁱ	0.88	2.02	2.8397 (17)	154
N16—H16···O2	0.88	2.27	2.7107 (17)	111
C1—H1A···Cg2ⁱⁱ	0.98	2.67	3.3101 (18)	123
C1—H1C···Cg1ⁱⁱⁱ	0.98	2.82	3.4955 (17)	127
C20—H20···Cg4^iv	0.95	2.99	3.8271 (18)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg4 are the centroids of the N16/N17/C15/C18/C23, N4/C3/C5/C12–C14 and C18–C23 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N16—H16⋯N17ⁱ	0.88	2.02	2.8397 (17)	154
N16—H16⋯O2	0.88	2.27	2.7107 (17)	111
C1—H1A⋯Cg2ⁱⁱ	0.98	2.67	3.3101 (18)	123
C1—H1C⋯Cg1ⁱⁱⁱ	0.98	2.82	3.4955 (17)	127
C20—H20⋯Cg4^iv	0.95	2.99	3.8271 (18)	148

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

2 in total

1. Parallel solution-phase synthesis of acrylonitrile scaffolds carrying L-alpha-amino acidic or D-glycosyl residues.

Authors: Stefania Fioravanti; Lucio Pellacani; Paolo A Tardella; Alberto Morreale; Giuseppe Del Signore
Journal: J Comb Chem Date: 2006 Nov-Dec

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