Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chloro­phen­yl)-4H-imidazo[4,5-b]pyridine

Bourichi, S.; Kandri Rodi, Y.; Hökelek, T.; Haoudi, A.; Renard, C.; Capet, F.

doi:10.1107/S2056989018017322

Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

S. Bourichi, Y. Kandri Rodi, T. Hökelek, A. Haoudi, C. Renard and F. Capet

The imidazo[4,5-b]pyridine unit is planar, while the phenyl and allyl substituents are rotated a little out of this plane. In the crystal, molecules are linked via pairs of the weak intermolecular C—H

N hydrogen bonds, forming inversion dimers with $R_{2}^{2}$ (20) ring motifs. The dimers are further connected by π–π stacking interactions between the imidazo[4,5-b]pyridine ring systems.

Keywords: crystal structure; imidazo[4,5-b]pyridine; Hirshfeld surface.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989018017322/is5505sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2056989018017322/is5505Isup2.hkl Contains datablock I
	Chemdraw file https://doi.org/10.1107/S2056989018017322/is5505Isup3.cdx Supplementary material
	Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989018017322/is5505Isup4.cml Supplementary material

CCDC reference: 1883384

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.035
wR factor = 0.089
Data-to-parameter ratio = 23.7

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.003 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         16 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   0 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: APEX2 (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2015).

4-Allyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine top

Crystal data top

C₁₅H₁₁BrClN₃	Z = 2
M_r = 348.63	F(000) = 348
Triclinic, P1	D_x = 1.641 Mg m⁻³
a = 7.6218 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5238 (5) Å	Cell parameters from 9961 reflections
c = 11.1093 (7) Å	θ = 2.4–25.8°
α = 95.739 (3)°	µ = 3.09 mm⁻¹
β = 98.880 (3)°	T = 296 K
γ = 94.979 (3)°	Plate, colourless
V = 705.66 (8) Å³	0.3 × 0.23 × 0.06 mm

Data collection top

Bruker APEX-II CCD diffractometer	3226 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.033
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 30.5°, θ_min = 1.9°
T_min = 0.591, T_max = 0.746	h = −10→10
31084 measured reflections	k = −12→12
4288 independent reflections	l = −15→15

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0395P)² + 0.2342P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
4288 reflections	Δρ_max = 0.57 e Å⁻³
181 parameters	Δρ_min = −0.47 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.17874 (3)	1.01452 (2)	0.68946 (2)	0.05997 (10)
Cl1	0.27559 (10)	−0.20635 (8)	0.05226 (6)	0.07320 (19)
N1	0.1843 (2)	0.4932 (2)	0.37610 (15)	0.0451 (4)
N2	0.3231 (2)	0.36057 (19)	0.53108 (14)	0.0408 (3)
N3	0.3389 (2)	0.57048 (19)	0.69517 (14)	0.0416 (3)
C1	0.3258 (3)	0.0867 (2)	0.36107 (18)	0.0460 (4)
H1	0.3669	0.0842	0.4441	0.055*
C2	0.3317 (3)	−0.0449 (3)	0.27905 (19)	0.0502 (5)
H2	0.3753	−0.1360	0.3063	0.060*
C3	0.2715 (3)	−0.0391 (3)	0.15560 (19)	0.0506 (5)
C4	0.2054 (3)	0.0941 (3)	0.11321 (19)	0.0538 (5)
H4	0.1664	0.0962	0.0299	0.065*
C5	0.1979 (3)	0.2241 (3)	0.19575 (19)	0.0493 (5)
H5	0.1515	0.3137	0.1678	0.059*
C6	0.2590 (3)	0.2232 (2)	0.32120 (17)	0.0420 (4)
C7	0.2538 (2)	0.3616 (2)	0.40937 (17)	0.0400 (4)
C8	0.2942 (2)	0.5038 (2)	0.57750 (16)	0.0390 (4)
C9	0.2078 (3)	0.5896 (2)	0.48503 (17)	0.0408 (4)
C10	0.1670 (3)	0.7408 (2)	0.51508 (19)	0.0453 (4)
H10	0.1095	0.7982	0.4567	0.054*
C11	0.2162 (3)	0.8041 (2)	0.63802 (19)	0.0444 (4)
C12	0.3010 (3)	0.7204 (2)	0.72501 (18)	0.0452 (4)
H12	0.3328	0.7673	0.8056	0.054*
C13	0.4300 (3)	0.4809 (3)	0.78916 (18)	0.0489 (5)
H13A	0.5192	0.5528	0.8446	0.059*
H13B	0.4916	0.4010	0.7491	0.059*
C14	0.3080 (3)	0.4023 (3)	0.8615 (2)	0.0550 (5)
H14	0.3600	0.3461	0.9228	0.066*
C15	0.1374 (4)	0.4035 (3)	0.8484 (3)	0.0709 (7)
H15A	0.0789	0.4579	0.7884	0.085*
H15B	0.0727	0.3499	0.8990	0.085*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.05960 (16)	0.03754 (12)	0.08491 (19)	0.00970 (9)	0.01673 (12)	0.00593 (10)
Cl1	0.0863 (5)	0.0732 (4)	0.0594 (3)	0.0184 (3)	0.0175 (3)	−0.0136 (3)
N1	0.0482 (9)	0.0466 (9)	0.0414 (8)	0.0074 (7)	0.0058 (7)	0.0105 (7)
N2	0.0446 (9)	0.0398 (8)	0.0399 (8)	0.0079 (7)	0.0079 (7)	0.0090 (6)
N3	0.0486 (9)	0.0397 (8)	0.0383 (8)	0.0076 (7)	0.0078 (7)	0.0100 (6)
C1	0.0462 (11)	0.0510 (11)	0.0425 (10)	0.0094 (9)	0.0090 (8)	0.0066 (8)
C2	0.0508 (12)	0.0515 (12)	0.0511 (11)	0.0131 (9)	0.0133 (9)	0.0050 (9)
C3	0.0479 (11)	0.0554 (12)	0.0489 (11)	0.0053 (9)	0.0158 (9)	−0.0042 (9)
C4	0.0542 (12)	0.0648 (14)	0.0407 (10)	0.0030 (10)	0.0055 (9)	0.0041 (9)
C5	0.0487 (11)	0.0521 (12)	0.0464 (10)	0.0054 (9)	0.0033 (9)	0.0092 (9)
C6	0.0370 (9)	0.0468 (11)	0.0426 (9)	0.0016 (8)	0.0086 (8)	0.0058 (8)
C7	0.0369 (9)	0.0427 (10)	0.0419 (9)	0.0040 (8)	0.0082 (7)	0.0094 (8)
C8	0.0390 (9)	0.0395 (9)	0.0410 (9)	0.0042 (7)	0.0095 (7)	0.0117 (7)
C9	0.0394 (10)	0.0421 (10)	0.0441 (9)	0.0056 (8)	0.0096 (8)	0.0145 (8)
C10	0.0441 (10)	0.0407 (10)	0.0546 (11)	0.0079 (8)	0.0094 (9)	0.0182 (9)
C11	0.0436 (10)	0.0347 (9)	0.0584 (11)	0.0048 (8)	0.0161 (9)	0.0094 (8)
C12	0.0508 (11)	0.0403 (10)	0.0458 (10)	0.0038 (8)	0.0130 (9)	0.0054 (8)
C13	0.0532 (12)	0.0523 (12)	0.0416 (10)	0.0121 (9)	0.0019 (9)	0.0107 (9)
C14	0.0662 (15)	0.0521 (12)	0.0472 (11)	0.0093 (10)	0.0024 (10)	0.0170 (9)
C15	0.0673 (17)	0.0755 (18)	0.0765 (17)	0.0097 (13)	0.0144 (13)	0.0348 (14)

Geometric parameters (Å, º) top

Br1—C11	1.886 (2)	C6—C1	1.395 (3)
Cl1—C3	1.744 (2)	C6—C5	1.401 (3)
N1—C7	1.342 (3)	C7—C6	1.464 (3)
N1—C9	1.371 (3)	C8—C9	1.431 (3)
N2—C7	1.375 (2)	C9—C10	1.373 (3)
N2—C8	1.327 (2)	C10—H10	0.9300
N3—C8	1.352 (2)	C11—C10	1.399 (3)
N3—C12	1.355 (3)	C11—C12	1.373 (3)
N3—C13	1.477 (2)	C12—H12	0.9300
C1—H1	0.9300	C13—H13A	0.9700
C1—C2	1.381 (3)	C13—H13B	0.9700
C2—H2	0.9300	C13—C14	1.480 (3)
C2—C3	1.384 (3)	C14—H14	0.9300
C4—H4	0.9300	C14—C15	1.287 (4)
C4—C3	1.378 (3)	C15—H15A	0.9300
C5—H5	0.9300	C15—H15B	0.9300
C5—C4	1.377 (3)

Br1···C14ⁱ	3.624 (2)	N3···H15A	2.5350
Br1···C15ⁱ	3.660 (3)	C1···C11ⁱⁱ	3.532 (3)
Br1···C2ⁱⁱ	3.677 (2)	C1···C12ⁱⁱ	3.472 (3)
Br1···C6ⁱⁱⁱ	3.729 (2)	C5···C13ⁱⁱ	3.595 (3)
Br1···H10^iv	3.1682	C6···C12ⁱⁱ	3.470 (3)
Cl1···H12^v	2.8304	C7···C8ⁱⁱ	3.512 (3)
Cl1···H14^vi	3.1002	C7···C10ⁱⁱⁱ	3.499 (3)
Cl1···H15B^vii	2.9750	C8···C15	3.559 (4)
N3···C6ⁱⁱ	3.437 (3)	C9···C9ⁱⁱⁱ	3.473 (3)
N1···H5	2.6087	C12···C15	3.378 (3)
N1···H15Aⁱⁱⁱ	2.5889	C5···H13Aⁱⁱ	2.8677
N2···H13B	2.5360	C12···H15A	2.8971
N2···H1	2.5251	H12···H13A	2.4427

C7—N1—C9	102.65 (16)	N2—C8—C9	111.53 (16)
C8—N2—C7	101.17 (15)	N3—C8—C9	120.81 (17)
C8—N3—C12	119.16 (16)	N1—C9—C8	107.12 (17)
C8—N3—C13	120.08 (16)	N1—C9—C10	132.60 (18)
C12—N3—C13	120.76 (16)	C10—C9—C8	120.27 (18)
C6—C1—H1	119.5	C9—C10—C11	116.59 (18)
C2—C1—C6	120.95 (19)	C9—C10—H10	121.7
C2—C1—H1	119.5	C11—C10—H10	121.7
C1—C2—H2	120.5	C10—C11—Br1	120.71 (15)
C1—C2—C3	118.9 (2)	C12—C11—Br1	117.03 (16)
C3—C2—H2	120.5	C12—C11—C10	122.18 (18)
C4—C3—Cl1	119.49 (17)	N3—C12—C11	120.99 (18)
C4—C3—C2	121.6 (2)	N3—C12—H12	119.5
C2—C3—Cl1	118.93 (18)	C11—C12—H12	119.5
C5—C4—H4	120.4	N3—C13—H13A	108.8
C5—C4—C3	119.2 (2)	N3—C13—H13B	108.8
C3—C4—H4	120.4	N3—C13—C14	113.74 (18)
C6—C5—H5	119.5	H13A—C13—H13B	107.7
C4—C5—C6	120.9 (2)	C14—C13—H13A	108.8
C4—C5—H5	119.5	C14—C13—H13B	108.8
C1—C6—C7	120.23 (17)	C13—C14—H14	116.6
C1—C6—C5	118.48 (19)	C15—C14—C13	126.8 (2)
C5—C6—C7	121.28 (18)	C15—C14—H14	116.6
N2—C7—C6	120.09 (17)	C14—C15—H15A	120.0
N1—C7—N2	117.53 (17)	C14—C15—H15B	120.0
N1—C7—C6	122.39 (17)	H15A—C15—H15B	120.0
N2—C8—N3	127.66 (17)

C9—N1—C7—N2	−0.3 (2)	C6—C5—C4—C3	1.1 (3)
C9—N1—C7—C6	−179.75 (17)	C5—C6—C1—C2	0.0 (3)
C7—N1—C9—C8	0.5 (2)	C7—C6—C1—C2	−179.96 (19)
C7—N1—C9—C10	179.6 (2)	C1—C6—C5—C4	−0.8 (3)
C8—N2—C7—N1	0.0 (2)	C7—C6—C5—C4	179.11 (19)
C8—N2—C7—C6	179.45 (17)	N1—C7—C6—C1	−177.28 (18)
C7—N2—C8—N3	−178.58 (19)	N1—C7—C6—C5	2.8 (3)
C7—N2—C8—C9	0.3 (2)	N2—C7—C6—C1	3.3 (3)
C12—N3—C8—N2	178.81 (19)	N2—C7—C6—C5	−176.66 (18)
C12—N3—C8—C9	0.0 (3)	N2—C8—C9—N1	−0.5 (2)
C13—N3—C8—N2	−0.5 (3)	N2—C8—C9—C10	−179.82 (17)
C13—N3—C8—C9	−179.29 (18)	N3—C8—C9—N1	178.47 (17)
C8—N3—C12—C11	0.8 (3)	N3—C8—C9—C10	−0.8 (3)
C13—N3—C12—C11	−179.93 (19)	N1—C9—C10—C11	−178.3 (2)
C8—N3—C13—C14	−97.3 (2)	C8—C9—C10—C11	0.8 (3)
C12—N3—C13—C14	83.4 (2)	C12—C11—C10—C9	0.0 (3)
C6—C1—C2—C3	0.6 (3)	Br1—C11—C10—C9	176.73 (14)
C1—C2—C3—Cl1	−178.98 (17)	Br1—C11—C12—N3	−177.67 (15)
C1—C2—C3—C4	−0.4 (3)	C10—C11—C12—N3	−0.8 (3)
C5—C4—C3—Cl1	178.14 (17)	N3—C13—C14—C15	1.2 (4)
C5—C4—C3—C2	−0.5 (3)

Symmetry codes: (i) x, y+1, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x, y−1, z−1; (vi) −x+1, −y, −z+1; (vii) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···N1ⁱⁱⁱ	0.93	2.59	3.454 (4)	155

Symmetry code: (iii) −x, −y+1, −z+1.

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Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chloro­phen­yl)-4H-imidazo[4,5-b]pyridine

Supporting information

Key indicators

checkCIF/PLATON results

Crystal structure and Hirshfeld surface analysis of 4-allyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine