6-Bromo-2-(4-meth­oxy­phen­yl)-3-methyl-3H-imidazo[4,5-b]pyridine

In the title compound, C₁₄H₁₂BrN₃O, the dihedral angle between the mean planes of the imidazo[4,5-b]pyridine ring system and the meth­oxy­phenyl ring is 41.53 (12)°. In the crystal, weak C—H...N hydrogen bonds link the mol­ecules into chains along the c-axis direction. Weak π–π stacking inter­actions involving the imidazole and the meth­oxy­phenyl rings further stabilize the crystal packing.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.107
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.825 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         16 Report

Alert level G
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min)           1 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         50 Note
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...         13 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          2 Note

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

6-Bromo-2-(4-methoxyphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Crystal data

C14H12BrN3O	F(000) = 640
Mr = 318.18	Dx = 1.617 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.8643 (6) Å	Cell parameters from 1624 reflections
b = 7.6795 (4) Å	θ = 3.8–71.4°
c = 12.0690 (5) Å	µ = 4.25 mm^−1
β = 108.465 (4)°	T = 293 K
V = 1306.75 (11) Å^3	Prism, colourless
Z = 4	0.26 × 0.24 × 0.12 mm

Data collection

Rigaku Oxford diffraction diffractometer	2477 independent reflections
Radiation source: fine-focus sealed X-ray tube, Enhance (Cu) X-ray Source	2015 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
Detector resolution: 16.0416 pixels mm^-1	θmax = 71.3°, θmin = 6.3°
ω scans	h = −17→18
Absorption correction: multi-scan (CrysAlis PRO; Rigaku Oxford Diffraction, 2015)	k = −9→7
Tmin = 0.354, Tmax = 1.000	l = −14→12
4519 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.039	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.0898P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.001
S = 1.05	Δρmax = 0.39 e Å^−3
2477 reflections	Δρmin = −0.37 e Å^−3
175 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0104 (5)
Primary atom site location: dual

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Br1	0.95243 (2)	0.30457 (6)	0.64922 (3)	0.0757 (2)
O1	0.14946 (16)	0.3891 (4)	0.0701 (2)	0.0741 (7)
N1	0.57950 (16)	0.3218 (3)	0.41193 (19)	0.0418 (5)
N2	0.60882 (15)	0.4032 (3)	0.24692 (17)	0.0367 (5)
N3	0.77969 (16)	0.4084 (3)	0.31660 (19)	0.0468 (5)
C1	0.54200 (18)	0.3648 (3)	0.3004 (2)	0.0371 (5)
C2	0.69556 (18)	0.3826 (3)	0.3305 (2)	0.0372 (5)
C3	0.8520 (2)	0.3820 (4)	0.4124 (3)	0.0506 (7)
H3	0.9130	0.3978	0.4088	0.061*
C4	0.8416 (2)	0.3316 (4)	0.5193 (2)	0.0476 (6)
C5	0.7541 (2)	0.3027 (4)	0.5315 (2)	0.0441 (6)
H5	0.7472	0.2658	0.6017	0.053*
C6	0.67646 (19)	0.3320 (3)	0.4325 (2)	0.0386 (6)
C7	0.43977 (18)	0.3688 (4)	0.2376 (2)	0.0403 (6)
C8	0.3766 (2)	0.4354 (4)	0.2917 (2)	0.0470 (6)
H8	0.3997	0.4782	0.3675	0.056*
C9	0.2809 (2)	0.4381 (4)	0.2341 (3)	0.0542 (7)
H9	0.2397	0.4818	0.2714	0.065*
C10	0.2451 (2)	0.3758 (4)	0.1202 (3)	0.0521 (7)
C11	0.3059 (2)	0.3046 (4)	0.0662 (3)	0.0499 (7)
H11	0.2822	0.2589	−0.0088	0.060*
C12	0.4027 (2)	0.3022 (3)	0.1251 (2)	0.0446 (6)
H12	0.4436	0.2551	0.0885	0.053*
C13	0.5959 (2)	0.4800 (4)	0.1325 (2)	0.0442 (6)
H13A	0.6519	0.5435	0.1341	0.066*
H13B	0.5425	0.5576	0.1131	0.066*
H13C	0.5846	0.3893	0.0749	0.066*
C15	0.1094 (3)	0.3397 (6)	−0.0496 (4)	0.0848 (13)
H15A	0.1385	0.4059	−0.0964	0.127*
H15B	0.0424	0.3621	−0.0749	0.127*
H15C	0.1202	0.2179	−0.0578	0.127*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Br1	0.0492 (2)	0.1056 (4)	0.0576 (3)	−0.01003 (18)	−0.00400 (16)	0.0134 (2)
O1	0.0440 (11)	0.0872 (17)	0.0781 (16)	−0.0058 (12)	0.0008 (11)	0.0013 (15)
N1	0.0420 (11)	0.0494 (13)	0.0327 (10)	−0.0049 (9)	0.0100 (9)	0.0067 (9)
N2	0.0451 (11)	0.0371 (11)	0.0284 (9)	0.0023 (9)	0.0123 (8)	0.0014 (8)
N3	0.0477 (12)	0.0560 (14)	0.0403 (11)	0.0020 (11)	0.0190 (10)	0.0032 (11)
C1	0.0437 (13)	0.0341 (13)	0.0319 (11)	−0.0015 (10)	0.0097 (10)	0.0027 (10)
C2	0.0457 (13)	0.0356 (13)	0.0310 (11)	0.0022 (10)	0.0133 (10)	−0.0011 (10)
C3	0.0449 (14)	0.0584 (18)	0.0505 (15)	−0.0022 (13)	0.0179 (12)	0.0009 (14)
C4	0.0438 (14)	0.0534 (17)	0.0393 (13)	−0.0015 (12)	0.0040 (11)	0.0009 (12)
C5	0.0487 (14)	0.0497 (16)	0.0318 (12)	−0.0059 (12)	0.0095 (11)	0.0031 (11)
C6	0.0447 (13)	0.0389 (14)	0.0323 (12)	−0.0045 (10)	0.0124 (10)	0.0019 (10)
C7	0.0429 (13)	0.0383 (13)	0.0371 (12)	−0.0017 (11)	0.0091 (10)	0.0075 (11)
C8	0.0507 (15)	0.0496 (16)	0.0400 (13)	−0.0034 (12)	0.0134 (11)	−0.0010 (12)
C9	0.0485 (15)	0.0588 (18)	0.0569 (17)	−0.0002 (14)	0.0190 (13)	−0.0031 (15)
C10	0.0460 (15)	0.0474 (16)	0.0561 (17)	−0.0068 (12)	0.0067 (13)	0.0070 (14)
C11	0.0547 (16)	0.0498 (17)	0.0388 (13)	−0.0116 (13)	0.0058 (12)	0.0007 (12)
C12	0.0521 (15)	0.0422 (15)	0.0390 (13)	−0.0050 (12)	0.0136 (12)	0.0002 (12)
C13	0.0535 (14)	0.0510 (16)	0.0296 (11)	0.0045 (12)	0.0153 (10)	0.0041 (11)
C15	0.061 (2)	0.086 (3)	0.080 (3)	−0.012 (2)	−0.016 (2)	0.001 (2)

Geometric parameters (Å, º)

Br1—C4	1.892 (3)	C7—C8	1.399 (4)
O1—C10	1.361 (4)	C7—C12	1.392 (4)
O1—C15	1.428 (5)	C8—H8	0.9300
N1—C1	1.325 (3)	C8—C9	1.371 (4)
N1—C6	1.385 (3)	C9—H9	0.9300
N2—C1	1.377 (3)	C9—C10	1.393 (4)
N2—C2	1.371 (3)	C10—C11	1.383 (5)
N2—C13	1.457 (3)	C11—H11	0.9300
N3—C2	1.328 (3)	C11—C12	1.388 (4)
N3—C3	1.321 (4)	C12—H12	0.9300
C1—C7	1.468 (3)	C13—H13A	0.9600
C2—C6	1.404 (3)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C3—C4	1.402 (4)	C15—H15A	0.9600
C4—C5	1.372 (4)	C15—H15B	0.9600
C5—H5	0.9300	C15—H15C	0.9600
C5—C6	1.392 (4)
C10—O1—C15	118.2 (3)	C7—C8—H8	119.6
C1—N1—C6	104.3 (2)	C9—C8—C7	120.8 (3)
C1—N2—C13	129.2 (2)	C9—C8—H8	119.6
C2—N2—C1	106.3 (2)	C8—C9—H9	119.8
C2—N2—C13	123.7 (2)	C8—C9—C10	120.4 (3)
C3—N3—C2	113.8 (2)	C10—C9—H9	119.8
N1—C1—N2	113.3 (2)	O1—C10—C9	115.6 (3)
N1—C1—C7	124.3 (2)	O1—C10—C11	124.5 (3)
N2—C1—C7	122.4 (2)	C11—C10—C9	119.9 (3)
N2—C2—C6	105.8 (2)	C10—C11—H11	120.3
N3—C2—N2	126.4 (2)	C10—C11—C12	119.3 (3)
N3—C2—C6	127.7 (2)	C12—C11—H11	120.3
N3—C3—H3	118.2	C7—C12—H12	119.3
N3—C3—C4	123.5 (3)	C11—C12—C7	121.4 (3)
C4—C3—H3	118.2	C11—C12—H12	119.3
C3—C4—Br1	118.2 (2)	N2—C13—H13A	109.5
C5—C4—Br1	120.0 (2)	N2—C13—H13B	109.5
C5—C4—C3	121.9 (3)	N2—C13—H13C	109.5
C4—C5—H5	122.0	H13A—C13—H13B	109.5
C4—C5—C6	116.0 (2)	H13A—C13—H13C	109.5
C6—C5—H5	122.0	H13B—C13—H13C	109.5
N1—C6—C2	110.3 (2)	O1—C15—H15A	109.5
N1—C6—C5	132.7 (2)	O1—C15—H15B	109.5
C5—C6—C2	117.1 (2)	O1—C15—H15C	109.5
C8—C7—C1	120.3 (2)	H15A—C15—H15B	109.5
C12—C7—C1	121.4 (3)	H15A—C15—H15C	109.5
C12—C7—C8	118.2 (3)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13C···N1^i	0.96	2.53	3.480 (3)	169

Symmetry code: (i) x, −y+1/2, z−1/2.