N-(tert-But­yl)-2-(2-nitro­phen­yl)imidazo[1,2-a]pyridin-3-amine

In the title compound, C₁₇H₁₈N₄O₂, the dihedral angle between the pyridine and benzene rings is 55.68 (11)°. In the crystal, N—H...N hydrogen bonds link the mol­ecules into [010] chains.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.048
• wR factor = 0.133
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         N4 Check
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of        C15 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         25 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....         21 Note

Alert level G
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        71% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT933_ALERT_2_G Number of OMIT Records in Embedded .res File ...          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          4 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 and SAINT (Bruker, 2016); data reduction: SAINT and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

N-(tert-Butyl)-2-(2-nitrophenyl)imidazo[1,2-a]pyridin-3-amine

Crystal data

C17H18N4O2	F(000) = 656
Mr = 310.35	Dx = 1.298 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.046 (7) Å	Cell parameters from 9919 reflections
b = 11.038 (10) Å	θ = 2.9–30.5°
c = 17.912 (15) Å	µ = 0.09 mm^−1
β = 93.47 (3)°	T = 296 K
V = 1588 (2) Å^3	Block, brown
Z = 4	0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEX2 CMOS diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	2430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω and φ scan	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −9→9
Tmin = 0.678, Tmax = 0.746	k = −13→13
27960 measured reflections	l = −21→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.9086P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2770 reflections	Δρmax = 0.20 e Å^−3
212 parameters	Δρmin = −0.20 e Å^−3

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
C1	0.30330 (19)	0.23121 (15)	0.15414 (9)	0.0301 (4)
C2	0.2519 (2)	0.17506 (17)	0.08591 (10)	0.0379 (4)
H2	0.274952	0.093657	0.078025	0.045*
C3	0.1687 (3)	0.24088 (19)	0.03207 (10)	0.0459 (5)
H3	0.133177	0.204120	−0.012811	0.055*
C4	0.1353 (3)	0.36484 (19)	0.04332 (11)	0.0486 (5)
H4	0.077691	0.408864	0.005807	0.058*
C5	0.1860 (2)	0.42014 (17)	0.10783 (10)	0.0394 (4)
H5	0.164764	0.502022	0.114921	0.047*
C6	0.33523 (19)	0.38898 (14)	0.23310 (9)	0.0279 (4)
C7	0.40432 (19)	0.28449 (15)	0.26309 (9)	0.0299 (4)
C8	0.4982 (2)	0.26944 (15)	0.33571 (9)	0.0326 (4)
C9	0.4610 (2)	0.18049 (16)	0.38715 (10)	0.0387 (4)
C10	0.5537 (3)	0.16271 (18)	0.45377 (11)	0.0493 (5)
H10	0.524721	0.102488	0.486886	0.059*
C11	0.6900 (3)	0.2359 (2)	0.47024 (12)	0.0534 (6)
H11	0.753904	0.225574	0.514800	0.064*
C12	0.7309 (3)	0.3245 (2)	0.42035 (13)	0.0535 (5)
H12	0.823182	0.373485	0.431392	0.064*
C13	0.6367 (2)	0.34146 (18)	0.35419 (11)	0.0425 (4)
H13	0.666250	0.402001	0.321398	0.051*
C15	0.1893 (2)	0.54261 (15)	0.30802 (10)	0.0355 (4)
C16	0.1656 (3)	0.67880 (18)	0.30153 (14)	0.0581 (6)
H16A	0.083002	0.704460	0.334670	0.087*
H16B	0.269065	0.718842	0.314819	0.087*
H16C	0.129591	0.699179	0.251009	0.087*
C17	0.2453 (3)	0.5097 (2)	0.38823 (12)	0.0607 (6)
H17A	0.160266	0.532130	0.420949	0.091*
H17B	0.264531	0.423958	0.391680	0.091*
H17C	0.346312	0.552144	0.402593	0.091*
C18	0.0280 (3)	0.4774 (2)	0.28534 (15)	0.0605 (6)
H18A	−0.055408	0.498849	0.319132	0.091*
H18B	−0.008882	0.500645	0.235408	0.091*
H18C	0.046138	0.391461	0.287147	0.091*
N1	0.26936 (16)	0.35359 (12)	0.16279 (7)	0.0289 (3)
N2	0.38504 (17)	0.18709 (13)	0.21493 (8)	0.0334 (3)
N3	0.31833 (18)	0.50905 (12)	0.25542 (8)	0.0315 (3)
N4	0.3144 (2)	0.10426 (16)	0.37388 (10)	0.0530 (5)
O1	0.3307 (3)	−0.00446 (17)	0.38458 (14)	0.1032 (8)
O2	0.1814 (2)	0.15316 (18)	0.35684 (9)	0.0685 (5)
H3A	0.410 (3)	0.544 (2)	0.2658 (12)	0.045 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (8)	0.0275 (8)	0.0324 (9)	0.0014 (6)	0.0033 (6)	−0.0013 (7)
C2	0.0429 (10)	0.0343 (9)	0.0364 (9)	0.0015 (7)	0.0011 (8)	−0.0052 (7)
C3	0.0528 (11)	0.0516 (12)	0.0324 (9)	0.0022 (9)	−0.0032 (8)	−0.0083 (8)
C4	0.0586 (12)	0.0519 (12)	0.0340 (10)	0.0139 (10)	−0.0082 (8)	0.0040 (8)
C5	0.0485 (10)	0.0346 (9)	0.0346 (9)	0.0094 (8)	−0.0014 (8)	0.0040 (7)
C6	0.0286 (8)	0.0269 (8)	0.0281 (8)	−0.0014 (6)	0.0018 (6)	0.0008 (6)
C7	0.0291 (8)	0.0295 (9)	0.0308 (8)	−0.0001 (6)	0.0006 (6)	0.0002 (6)
C8	0.0344 (8)	0.0287 (8)	0.0341 (9)	0.0065 (7)	−0.0019 (7)	−0.0011 (7)
C9	0.0457 (10)	0.0325 (9)	0.0371 (9)	0.0030 (8)	−0.0037 (8)	0.0005 (7)
C10	0.0678 (13)	0.0388 (10)	0.0398 (10)	0.0066 (9)	−0.0090 (9)	0.0062 (8)
C11	0.0628 (13)	0.0491 (12)	0.0454 (11)	0.0098 (10)	−0.0210 (10)	−0.0016 (9)
C12	0.0480 (11)	0.0521 (12)	0.0577 (13)	−0.0014 (9)	−0.0179 (10)	−0.0033 (10)
C13	0.0407 (10)	0.0409 (10)	0.0448 (11)	−0.0020 (8)	−0.0051 (8)	0.0026 (8)
C15	0.0380 (9)	0.0287 (9)	0.0405 (10)	0.0012 (7)	0.0089 (7)	−0.0022 (7)
C16	0.0647 (14)	0.0332 (11)	0.0792 (16)	0.0088 (9)	0.0255 (12)	−0.0001 (10)
C17	0.0765 (16)	0.0661 (15)	0.0409 (11)	0.0157 (12)	0.0149 (11)	−0.0004 (10)
C18	0.0394 (11)	0.0638 (14)	0.0799 (16)	−0.0092 (10)	0.0179 (11)	−0.0181 (12)
N1	0.0311 (7)	0.0266 (7)	0.0290 (7)	0.0024 (5)	0.0013 (5)	0.0015 (5)
N2	0.0369 (8)	0.0288 (7)	0.0342 (8)	0.0045 (6)	−0.0004 (6)	−0.0007 (6)
N3	0.0318 (8)	0.0258 (7)	0.0372 (8)	−0.0029 (6)	0.0040 (6)	−0.0021 (6)
N4	0.0664 (12)	0.0468 (11)	0.0445 (10)	−0.0142 (9)	−0.0074 (8)	0.0111 (8)
O1	0.1304 (19)	0.0502 (11)	0.1245 (19)	−0.0298 (11)	−0.0298 (15)	0.0251 (11)
O2	0.0582 (10)	0.0850 (13)	0.0613 (10)	−0.0176 (9)	−0.0049 (8)	0.0064 (9)

Geometric parameters (Å, º)

C1—N2	1.330 (2)	C11—C12	1.378 (3)
C1—N1	1.389 (2)	C11—H11	0.9300
C1—C2	1.410 (3)	C12—C13	1.380 (3)
C2—C3	1.352 (3)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.411 (3)	C15—N3	1.490 (2)
C3—H3	0.9300	C15—C18	1.518 (3)
C4—C5	1.348 (3)	C15—C16	1.519 (3)
C4—H4	0.9300	C15—C17	1.523 (3)
C5—N1	1.371 (2)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—C7	1.375 (2)	C16—H16C	0.9600
C6—N1	1.392 (2)	C17—H17A	0.9600
C6—N3	1.393 (2)	C17—H17B	0.9600
C7—N2	1.381 (2)	C17—H17C	0.9600
C7—C8	1.473 (2)	C18—H18A	0.9600
C8—C9	1.391 (3)	C18—H18B	0.9600
C8—C13	1.392 (3)	C18—H18C	0.9600
C9—C10	1.382 (3)	N3—H3A	0.85 (2)
C9—N4	1.457 (3)	N4—O2	1.221 (3)
C10—C11	1.380 (3)	N4—O1	1.221 (3)
C10—H10	0.9300
N2—C1—N1	110.84 (14)	C12—C13—H13	119.4
N2—C1—C2	130.80 (16)	C8—C13—H13	119.4
N1—C1—C2	118.36 (15)	N3—C15—C18	109.28 (16)
C3—C2—C1	119.26 (18)	N3—C15—C16	106.68 (15)
C3—C2—H2	120.4	C18—C15—C16	110.31 (18)
C1—C2—H2	120.4	N3—C15—C17	111.07 (16)
C2—C3—C4	120.63 (18)	C18—C15—C17	109.77 (18)
C2—C3—H3	119.7	C16—C15—C17	109.69 (18)
C4—C3—H3	119.7	C15—C16—H16A	109.5
C5—C4—C3	120.74 (17)	C15—C16—H16B	109.5
C5—C4—H4	119.6	H16A—C16—H16B	109.5
C3—C4—H4	119.6	C15—C16—H16C	109.5
C4—C5—N1	118.85 (18)	H16A—C16—H16C	109.5
C4—C5—H5	120.6	H16B—C16—H16C	109.5
N1—C5—H5	120.6	C15—C17—H17A	109.5
C7—C6—N1	103.93 (14)	C15—C17—H17B	109.5
C7—C6—N3	136.86 (16)	H17A—C17—H17B	109.5
N1—C6—N3	119.21 (14)	C15—C17—H17C	109.5
C6—C7—N2	112.41 (15)	H17A—C17—H17C	109.5
C6—C7—C8	127.80 (15)	H17B—C17—H17C	109.5
N2—C7—C8	119.72 (15)	C15—C18—H18A	109.5
C9—C8—C13	116.53 (16)	C15—C18—H18B	109.5
C9—C8—C7	123.01 (16)	H18A—C18—H18B	109.5
C13—C8—C7	120.37 (16)	C15—C18—H18C	109.5
C10—C9—C8	123.05 (18)	H18A—C18—H18C	109.5
C10—C9—N4	116.62 (17)	H18B—C18—H18C	109.5
C8—C9—N4	120.27 (16)	C5—N1—C1	122.15 (15)
C11—C10—C9	118.80 (19)	C5—N1—C6	129.96 (15)
C11—C10—H10	120.6	C1—N1—C6	107.89 (13)
C9—C10—H10	120.6	C1—N2—C7	104.93 (14)
C12—C11—C10	119.67 (18)	C6—N3—C15	120.11 (14)
C12—C11—H11	120.2	C6—N3—H3A	113.4 (15)
C10—C11—H11	120.2	C15—N3—H3A	112.5 (15)
C11—C12—C13	120.8 (2)	O2—N4—O1	123.9 (2)
C11—C12—H12	119.6	O2—N4—C9	118.32 (18)
C13—C12—H12	119.6	O1—N4—C9	117.6 (2)
C12—C13—C8	121.11 (19)
N2—C1—C2—C3	179.80 (18)	C4—C5—N1—C1	0.0 (3)
N1—C1—C2—C3	−1.4 (2)	C4—C5—N1—C6	179.30 (17)
C1—C2—C3—C4	0.8 (3)	N2—C1—N1—C5	−179.99 (15)
C2—C3—C4—C5	0.2 (3)	C2—C1—N1—C5	1.0 (2)
C3—C4—C5—N1	−0.6 (3)	N2—C1—N1—C6	0.59 (18)
N1—C6—C7—N2	0.24 (18)	C2—C1—N1—C6	−178.43 (14)
N3—C6—C7—N2	−179.97 (17)	C7—C6—N1—C5	−179.84 (16)
N1—C6—C7—C8	177.11 (15)	N3—C6—N1—C5	0.3 (2)
N3—C6—C7—C8	−3.1 (3)	C7—C6—N1—C1	−0.49 (16)
C6—C7—C8—C9	129.2 (2)	N3—C6—N1—C1	179.68 (14)
N2—C7—C8—C9	−54.2 (2)	N1—C1—N2—C7	−0.43 (17)
C6—C7—C8—C13	−54.4 (3)	C2—C1—N2—C7	178.44 (17)
N2—C7—C8—C13	122.28 (19)	C6—C7—N2—C1	0.11 (18)
C13—C8—C9—C10	0.4 (3)	C8—C7—N2—C1	−177.04 (14)
C7—C8—C9—C10	176.93 (17)	C7—C6—N3—C15	−77.9 (3)
C13—C8—C9—N4	177.47 (17)	N1—C6—N3—C15	101.86 (18)
C7—C8—C9—N4	−5.9 (3)	C18—C15—N3—C6	−43.1 (2)
C8—C9—C10—C11	−0.3 (3)	C16—C15—N3—C6	−162.30 (17)
N4—C9—C10—C11	−177.48 (19)	C17—C15—N3—C6	78.2 (2)
C9—C10—C11—C12	−0.1 (3)	C10—C9—N4—O2	128.0 (2)
C10—C11—C12—C13	0.4 (3)	C8—C9—N4—O2	−49.3 (3)
C11—C12—C13—C8	−0.3 (3)	C10—C9—N4—O1	−48.0 (3)
C9—C8—C13—C12	−0.1 (3)	C8—C9—N4—O1	134.7 (2)
C7—C8—C13—C12	−176.75 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2^i	0.85 (2)	2.29 (2)	3.112 (3)	164 (2)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.