6-Bromo-3-(2-methyl­propen­yl)imidazo[1,2-a]pyridine

The title compound, C₁₁H₁₁BrN₂, is a new imidazo[1,2-a]pyridine-conjugated alkene derivative. It contains a planar imidazo[1,2-a]pyridine ring system and a vinyl double bond, which is not in the plane of the heterocycle.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.005 Å
• R factor = 0.038
• wR factor = 0.114
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

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Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: CrystalStructure.

6-Bromo-3-(2-methylpropenyl)imidazo[1,2-a]pyridine

Crystal data

C11H11BrN2	Z = 2
Mr = 251.13	F(000) = 252.00
Triclinic, P1	Dx = 1.610 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.7107 Å
a = 6.5532 (6) Å	Cell parameters from 2749 reflections
b = 7.594 (1) Å	θ = 2.7–27.5°
c = 11.026 (1) Å	µ = 3.94 mm^−1
α = 87.773 (3)°	T = 295 K
β = 73.715 (2)°	Chunk, colorless
γ = 79.578 (4)°	0.30 × 0.28 × 0.26 mm
V = 518.0 (1) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	1906 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.042
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −8→8
Tmin = 0.323, Tmax = 0.359	k = −9→9
4757 measured reflections	l = −14→11
2338 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0014Fo^2 + 1.3σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.038	(Δ/σ)max < 0.001
wR(F^2) = 0.114	Δρmax = 0.43 e Å^−3
S = 1.01	Δρmin = −0.42 e Å^−3
2243 reflections	Extinction correction: Larson (1970), equation 22
128 parameters	Extinction coefficient: 27 (7)
H-atom parameters constrained

Special details

Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.91071 (5)	0.06232 (5)	−0.20117 (3)	0.0565 (1)
N1	0.1140 (4)	0.4294 (4)	0.1690 (3)	0.0468 (7)
N4	0.4609 (3)	0.2919 (3)	0.1142 (2)	0.0344 (6)
C2	0.1989 (5)	0.4206 (4)	0.2709 (3)	0.0445 (8)
C3	0.4109 (4)	0.3371 (4)	0.2413 (3)	0.0382 (7)
C5	0.6489 (4)	0.2069 (4)	0.0327 (3)	0.0385 (7)
C6	0.6526 (5)	0.1793 (4)	−0.0875 (3)	0.0417 (7)
C7	0.4675 (6)	0.2363 (5)	−0.1319 (3)	0.0490 (9)
C8	0.2831 (5)	0.3197 (5)	−0.0508 (3)	0.0488 (9)
C9	0.2738 (5)	0.3509 (4)	0.0753 (3)	0.0400 (7)
C10	0.5730 (4)	0.3017 (4)	0.3101 (3)	0.0415 (7)
C11	0.5432 (5)	0.2659 (4)	0.4319 (3)	0.0398 (7)
C12	0.3314 (5)	0.2466 (5)	0.5230 (3)	0.0530 (9)
C13	0.7278 (5)	0.2393 (5)	0.4899 (3)	0.0505 (9)
H1	0.1167	0.4688	0.3551	0.052*
H2	0.7780	0.1670	0.0616	0.045*
H3	0.4737	0.2152	−0.2201	0.060*
H4	0.1545	0.3587	−0.0804	0.060*
H5	0.7221	0.3045	0.2607	0.050*
H6	0.2589	0.3612	0.5604	0.063*
H7	0.3559	0.1644	0.5879	0.063*
H8	0.2436	0.2019	0.4790	0.063*
H9	0.7237	0.3473	0.5337	0.063*
H10	0.7160	0.1422	0.5484	0.063*
H11	0.8617	0.2123	0.4246	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0548 (3)	0.0634 (3)	0.0408 (2)	0.0031 (2)	−0.0041 (1)	−0.0061 (1)
N1	0.033 (1)	0.053 (2)	0.053 (1)	−0.000 (1)	−0.015 (1)	0.004 (1)
N4	0.030 (1)	0.040 (1)	0.035 (1)	−0.0048 (9)	−0.0118 (9)	0.0037 (9)
C2	0.039 (1)	0.048 (2)	0.044 (2)	−0.005 (1)	−0.008 (1)	0.000 (1)
C3	0.034 (1)	0.044 (2)	0.035 (1)	−0.008 (1)	−0.008 (1)	0.002 (1)
C5	0.033 (1)	0.044 (2)	0.037 (1)	−0.003 (1)	−0.010 (1)	0.005 (1)
C6	0.041 (1)	0.046 (2)	0.035 (1)	−0.005 (1)	−0.008 (1)	0.002 (1)
C7	0.057 (2)	0.057 (2)	0.037 (2)	−0.010 (1)	−0.020 (1)	0.005 (1)
C8	0.044 (1)	0.058 (2)	0.049 (2)	−0.005 (1)	−0.024 (1)	0.010 (1)
C9	0.036 (1)	0.041 (2)	0.045 (2)	−0.006 (1)	−0.017 (1)	0.009 (1)
C10	0.030 (1)	0.054 (2)	0.040 (1)	−0.005 (1)	−0.010 (1)	−0.004 (1)
C11	0.038 (1)	0.042 (2)	0.040 (1)	−0.005 (1)	−0.011 (1)	−0.003 (1)
C12	0.045 (2)	0.064 (2)	0.049 (2)	−0.014 (1)	−0.009 (1)	0.010 (2)
C13	0.047 (2)	0.063 (2)	0.047 (2)	−0.008 (1)	−0.022 (1)	−0.006 (1)

Geometric parameters (Å, º)

Br1—C6	1.891 (3)	C11—C12	1.495 (4)
N1—C2	1.381 (5)	C11—C13	1.500 (5)
N1—C9	1.317 (4)	C2—H1	0.9800
N4—C3	1.389 (4)	C5—H2	0.9800
N4—C5	1.370 (3)	C7—H3	0.9800
N4—C9	1.404 (4)	C8—H4	0.9800
C2—C3	1.372 (4)	C10—H5	0.9800
C3—C10	1.452 (4)	C12—H6	0.9600
C5—C6	1.343 (4)	C12—H7	0.9600
C6—C7	1.423 (5)	C12—H8	0.9600
C7—C8	1.349 (4)	C13—H9	0.9600
C8—C9	1.402 (5)	C13—H10	0.9600
C10—C11	1.326 (4)	C13—H11	0.9600
Br1···C5	2.803 (2)	C9···H3	3.2807
Br1···C7	2.866 (3)	C9···H4	2.0703
N1···N4	2.246 (3)	C9···H4^ii	3.2287
N1···C3	2.291 (4)	C10···H1	2.9396
N1···C5	3.536 (3)	C10···H2	2.8312
N1···C6^i	3.555 (4)	C10···H6	2.9382
N1···C8	2.473 (4)	C10···H6^viii	3.4633
N1···C8^ii	3.466 (4)	C10···H7	3.2151
N4···C2	2.179 (3)	C10···H8	2.6324
N4···C6	2.334 (3)	C10···H9	2.9546
N4···C7	2.749 (4)	C10···H9^viii	3.2333
N4···C8	2.405 (4)	C10···H10	3.1574
N4···C10	2.476 (4)	C10···H11	2.5385
C2···C5	3.533 (3)	C11···H1	3.2511
C2···C8	3.526 (5)	C11···H5	1.9660
C2···C9	2.139 (4)	C11···H6	2.0283
C2···C10	2.603 (4)	C11···H6^viii	3.3348
C2···C11	3.278 (5)	C11···H7	2.0282
C2···C12	3.298 (5)	C11···H7^ix	3.2181
C3···C5	2.512 (3)	C11···H8	2.0282
C3···C7^i	3.561 (5)	C11···H9	2.0260
C3···C8	3.561 (5)	C11···H9^viii	3.1125
C3···C9	2.246 (5)	C11···H10	2.0374
C3···C11	2.494 (4)	C11···H11	2.0325
C3···C12	3.073 (4)	C12···H1	2.9344
C5···C7	2.416 (5)	C12···H1^vii	3.2890
C5···C8	2.786 (5)	C12···H3^x	3.2098
C5···C9	2.425 (4)	C12···H5	3.3566
C5···C9^i	3.594 (4)	C12···H7^ix	3.4662
C5···C10	3.051 (4)	C12···H9	2.8449
C6···N1^i	3.555 (4)	C12···H9^viii	3.0995
C6···C8	2.390 (4)	C12···H10	2.5912
C6···C9	2.756 (4)	C12···H10^ix	3.1752
C7···C3^i	3.561 (5)	C12···H11^vi	3.5921
C7···C9	2.391 (4)	C12···H11	3.3015
C8···N1^ii	3.466 (4)	C13···H1^iii	3.3194
C9···C5^i	3.594 (4)	C13···H1^viii	3.3111
C10···C12	2.504 (4)	C13···H3^x	3.1800
C10···C13	2.463 (5)	C13···H5	2.5656
C12···C13	2.510 (5)	C13···H6	2.9313
Br1···H2	2.8807	C13···H6^viii	3.0752
Br1···H3	2.9503	C13···H7	2.5316
Br1···H4^iii	3.4816	C13···H7^ix	3.3933
Br1···H7^iv	3.3755	C13···H8	3.2722
Br1···H10^v	3.3451	C13···H8^iii	3.3086
N1···H1	2.0903	C13···H8^ix	3.3314
N1···H4	2.7518	H1···C12^vii	3.2890
N1···H4^ii	2.5412	H1···C13^vi	3.3194
N1···H5^vi	2.8049	H1···C13^viii	3.3111
N1···H6^vii	3.5033	H2···C8^iii	3.5795
N1···H11^vi	3.3776	H3···C3^i	3.5989
N4···H1	3.1254	H3···C12^v	3.2098
N4···H2	2.0513	H3···C13^v	3.1800
N4···H4	3.2944	H4···Br1^vi	3.4816
N4···H5	2.6775	H4···N1^ii	2.5412
C2···H5^vi	3.4285	H4···C5^vi	3.5802
C2···H5	3.3530	H4···C8^ii	3.4200
C2···H6	3.3281	H4···C9^ii	3.2287
C2···H6^vii	3.2427	H5···N1^iii	2.8049
C2···H8	2.8311	H5···C2^iii	3.4285
C2···H9^viii	3.0393	H6···N1^vii	3.5033
C2···H11^vi	3.0356	H6···C2^vii	3.2427
C3···H1	2.0820	H6···C10^viii	3.4633
C3···H2	2.7899	H6···C11^viii	3.3348
C3···H3^i	3.5989	H6···C13^viii	3.0752
C3···H5	2.0789	H7···Br1^xi	3.3755
C3···H6	3.3799	H7···C7^x	3.4526
C3···H8	2.7771	H7···C11^ix	3.2181
C3···H9^viii	3.3385	H7···C12^ix	3.4662
C5···H3	3.2930	H7···C13^ix	3.3933
C5···H4^iii	3.5802	H8···C13^vi	3.3086
C5···H5	2.8370	H8···C13^ix	3.3314
C6···H2	2.0261	H9···C2^viii	3.0393
C6···H3	2.0974	H9···C3^viii	3.3385
C6···H4	3.2820	H9···C10^viii	3.2333
C7···H2	3.3059	H9···C11^viii	3.1125
C7···H4	2.0226	H9···C12^viii	3.0995
C7···H7^v	3.4526	H10···Br1^x	3.3451
C7···H10^v	3.4855	H10···C7^x	3.4855
C8···H2^vi	3.5795	H10···C12^ix	3.1752
C8···H3	2.0301	H11···N1^iii	3.3776
C8···H4^ii	3.4200	H11···C2^iii	3.0356
C9···H1	3.0790	H11···C12^iii	3.5921
C9···H2	3.3104
Br1—C6—C5	119.2 (2)	N4—C5—H2	120.6512
Br1—C6—C7	119.0 (2)	H1—C2—C3	123.6985
N1—C2—C3	112.6 (3)	C3—C10—H5	116.1437
C9—N1—C2	104.8 (3)	H2—C5—C6	120.6491
N1—C9—N4	111.2 (3)	C6—C7—H3	120.4560
N1—C9—C8	130.8 (3)	H3—C7—C8	120.4550
C5—N4—C3	131.1 (3)	C7—C8—H4	119.6834
N4—C3—C2	104.2 (3)	H4—C8—C9	119.6706
C9—N4—C3	107.1 (2)	H5—C10—C11	116.1477
N4—C3—C10	121.3 (2)	C11—C12—H6	109.4744
N4—C5—C6	118.7 (3)	C11—C12—H8	109.4673
C9—N4—C5	121.8 (2)	C11—C12—H7	109.4686
N4—C9—C8	118.0 (2)	C11—C13—H9	108.9247
C2—C3—C10	134.3 (3)	C11—C13—H10	109.9005
C3—C10—C11	127.7 (3)	C11—C13—H11	109.4737
C5—C6—C7	121.7 (2)	H8—C12—H6	109.4705
C6—C7—C8	119.1 (3)	H7—C12—H6	109.4723
C7—C8—C9	120.6 (3)	H8—C12—H7	109.4743
C10—C11—C12	125.0 (3)	H10—C13—H9	109.4721
C10—C11—C13	121.1 (3)	H11—C13—H9	109.7492
C13—C11—C12	113.9 (3)	H11—C13—H10	109.3078
N1—C2—H1	123.6917
C9—N1—C2—C3	0.0 (3)	N4—C3—C10—C11	−149.6 (3)
C2—N1—C9—N4	−0.2 (3)	N4—C5—C6—Br1	180.0 (2)
C2—N1—C9—C8	179.8 (3)	Br1—C6—C7—C8	179.9 (2)
C5—N4—C3—C2	179.7 (3)	C6—C7—C8—C9	0.4 (5)
C3—N4—C5—C6	179.9 (3)	C7—C8—C9—N1	179.6 (3)
C3—N4—C9—N1	0.3 (3)	C7—C8—C9—N4	−0.4 (5)
C3—N4—C9—C8	−179.7 (3)	C3—C10—C11—C12	3.0 (6)
N1—C2—C3—N4	0.1 (3)

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