Crystal structure of (E)-4-[N-(7-methyl-2-phenyl-imidazo[1,2-a]pyridin-3-yl)carboximido-yl]phenol.

The mol-ecule of the title compound, C21H17N3O, is built up from fused five- and six-membered rings connected to a methyl group, a phenyl ring and an (imino-meth-yl)phenol group. The fused ring system is almost planar (r.m.s. deviation = 0.031 Å) and forms dihedral angles of 64.97 (7) and 18.52 (6)° with the phenyl ring and the (imino-meth-yl)phenol group, respectively. In the crystal, centrosymmetric mol-ecules are linked by pairs of C-H⋯π inter-actions into dimeric units, which are further connected by O-H⋯N hydrogen bonds to form layers parallel to (101).

Related literature

For the biological activities of imidazo[1,2a]pyridine derivatives, see: Solomons et al. (1997 ▸); Bhandari et al. (2008 ▸); Ertl et al. (2000 ▸). For the synthesis of related compounds, see: Radi et al. (2015 ▸); Elaatiaoui et al. (2014 ▸).

Experimental

Crystal data

C21H17N3O

M = 327.38

Monoclinic

a = 12.295 (3) Å

b = 9.587 (2) Å

c = 14.977 (4) Å

β = 101.548 (1)°

V = 1729.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.42 × 0.31 × 0.26 mm

Data collection

Bruker X8 APEX Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.673, T max = 0.746

26727 measured reflections

4126 independent reflections

2970 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.140

S = 1.02

4126 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015017843/rz5169sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015017843/rz5169Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S2056989015017843/rz5169fig1.tif

The mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles of arbitrary radius.

Click here for additional data file.

. DOI: 10.1107/S2056989015017843/rz5169fig2.tif

Packing diagram of the title compound showing the fornation of a layer parallel to the (1 0 1) plane by O—H⋯N hydrogen bonds cyan dotted lines) and C—H⋯π hydrogen inter­actions (red dotted lines). Hydrogen atoms not invoolved in hydrogen bonding are omitted.

CCDC reference: 1426925

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H17N3O	F(000) = 688
Mr = 327.38	Dx = 1.257 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.295 (3) Å	Cell parameters from 4126 reflections
b = 9.587 (2) Å	θ = 2.4–27.9°
c = 14.977 (4) Å	µ = 0.08 mm−1
β = 101.548 (1)°	T = 296 K
V = 1729.6 (7) Å3	Block, green
Z = 4	0.42 × 0.31 × 0.26 mm

Bruker X8 APEX Diffractometer	4126 independent reflections
Radiation source: fine-focus sealed tube	2970 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.673, Tmax = 0.746	k = −12→12
26727 measured reflections	l = −15→19

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.140	w = 1/[σ2(Fo2) + (0.0656P)2 + 0.4096P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
4126 reflections	Δρmax = 0.30 e Å−3
226 parameters	Δρmin = −0.18 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.

	x	y	z	Uiso*/Ueq
C1	0.54952 (12)	0.49279 (15)	0.29735 (10)	0.0451 (3)
C2	0.50833 (14)	0.40312 (17)	0.22392 (11)	0.0535 (4)
H2	0.5552	0.3713	0.1867	0.064*
C3	0.39967 (15)	0.36297 (19)	0.20743 (12)	0.0615 (4)
C4	0.33099 (15)	0.4141 (2)	0.26548 (14)	0.0695 (5)
H4	0.2572	0.3858	0.2555	0.083*
C5	0.36876 (13)	0.5026 (2)	0.33486 (13)	0.0620 (5)
H5	0.3219	0.5349	0.3719	0.074*
C6	0.53862 (12)	0.62960 (16)	0.41673 (10)	0.0452 (3)
C7	0.64653 (12)	0.62297 (15)	0.40304 (9)	0.0418 (3)
C8	0.75103 (12)	0.68006 (16)	0.45771 (9)	0.0436 (3)
C9	0.83189 (14)	0.58748 (19)	0.50032 (11)	0.0561 (4)
H9	0.8193	0.4920	0.4940	0.067*
C10	0.93079 (16)	0.6352 (2)	0.55190 (12)	0.0696 (5)
H10	0.9839	0.5719	0.5805	0.083*
C11	0.95080 (16)	0.7758 (3)	0.56102 (14)	0.0751 (6)
H11	1.0170	0.8079	0.5964	0.090*
C12	0.87302 (17)	0.8688 (2)	0.51789 (14)	0.0727 (5)
H12	0.8872	0.9641	0.5232	0.087*
C13	0.77345 (14)	0.82168 (18)	0.46638 (12)	0.0579 (4)
H13	0.7212	0.8856	0.4374	0.069*
C14	0.52384 (14)	0.78868 (19)	0.52891 (12)	0.0562 (4)
H14	0.5941	0.8193	0.5237	0.067*
C15	0.47106 (12)	0.85783 (17)	0.59525 (10)	0.0484 (4)
C16	0.36939 (12)	0.81542 (16)	0.61444 (10)	0.0470 (3)
H16	0.3318	0.7408	0.5826	0.056*
C17	0.32421 (12)	0.88222 (16)	0.67956 (10)	0.0464 (3)
H17	0.2574	0.8511	0.6924	0.056*
C18	0.37814 (12)	0.99643 (16)	0.72644 (10)	0.0457 (3)
C19	0.47875 (13)	1.04114 (19)	0.70700 (11)	0.0556 (4)
H19	0.5152	1.1177	0.7373	0.067*
C20	0.52369 (13)	0.9715 (2)	0.64294 (11)	0.0586 (4)
H20	0.5914	1.0013	0.6311	0.070*
C21	0.3546 (2)	0.2628 (2)	0.13212 (16)	0.0885 (7)
H21A	0.2772	0.2469	0.1308	0.133*
H21B	0.3636	0.3014	0.0749	0.133*
H21C	0.3942	0.1761	0.1425	0.133*
N1	0.65214 (10)	0.53861 (13)	0.32982 (8)	0.0456 (3)
N2	0.47802 (10)	0.54401 (13)	0.34959 (8)	0.0465 (3)
N3	0.48107 (11)	0.68926 (14)	0.47735 (9)	0.0506 (3)
O1	0.33670 (9)	1.06880 (13)	0.78932 (7)	0.0589 (3)
H1	0.2777	1.0339	0.7953	0.088*

	U11	U22	U33	U12	U13	U23
C1	0.0404 (7)	0.0465 (8)	0.0483 (8)	0.0019 (6)	0.0084 (6)	0.0070 (6)
C2	0.0550 (9)	0.0524 (9)	0.0513 (9)	−0.0014 (7)	0.0063 (7)	0.0013 (7)
C3	0.0577 (10)	0.0605 (10)	0.0600 (10)	−0.0065 (8)	−0.0028 (8)	0.0048 (8)
C4	0.0408 (9)	0.0817 (13)	0.0793 (13)	−0.0094 (9)	−0.0039 (8)	0.0051 (10)
C5	0.0361 (8)	0.0752 (11)	0.0742 (11)	0.0034 (8)	0.0096 (8)	0.0066 (9)
C6	0.0412 (8)	0.0482 (8)	0.0463 (8)	0.0044 (6)	0.0095 (6)	0.0059 (6)
C7	0.0411 (7)	0.0428 (7)	0.0422 (7)	0.0013 (6)	0.0096 (6)	0.0064 (6)
C8	0.0408 (7)	0.0510 (8)	0.0399 (7)	−0.0002 (6)	0.0106 (6)	0.0044 (6)
C9	0.0544 (9)	0.0591 (9)	0.0527 (9)	0.0081 (8)	0.0053 (7)	0.0004 (7)
C10	0.0537 (10)	0.0908 (14)	0.0582 (10)	0.0154 (10)	−0.0031 (8)	−0.0059 (10)
C11	0.0495 (10)	0.1046 (16)	0.0673 (12)	−0.0103 (11)	0.0020 (8)	−0.0204 (11)
C12	0.0654 (12)	0.0690 (12)	0.0826 (13)	−0.0206 (10)	0.0119 (10)	−0.0095 (10)
C13	0.0540 (9)	0.0538 (9)	0.0642 (10)	−0.0036 (8)	0.0078 (8)	0.0086 (8)
C14	0.0481 (9)	0.0665 (10)	0.0577 (9)	0.0027 (8)	0.0193 (7)	0.0031 (8)
C15	0.0444 (8)	0.0551 (9)	0.0469 (8)	0.0026 (7)	0.0121 (6)	0.0052 (7)
C16	0.0457 (8)	0.0453 (8)	0.0497 (8)	0.0000 (6)	0.0092 (6)	0.0052 (6)
C17	0.0381 (7)	0.0524 (8)	0.0500 (8)	−0.0015 (6)	0.0118 (6)	0.0073 (7)
C18	0.0406 (8)	0.0560 (8)	0.0403 (7)	0.0008 (6)	0.0077 (6)	0.0037 (6)
C19	0.0467 (8)	0.0688 (10)	0.0520 (9)	−0.0129 (8)	0.0116 (7)	−0.0071 (8)
C20	0.0435 (8)	0.0778 (11)	0.0576 (9)	−0.0110 (8)	0.0180 (7)	−0.0022 (8)
C21	0.0867 (15)	0.0875 (15)	0.0824 (14)	−0.0259 (12)	−0.0044 (12)	−0.0115 (12)
N1	0.0410 (6)	0.0489 (7)	0.0476 (7)	−0.0011 (5)	0.0108 (5)	0.0019 (5)
N2	0.0366 (6)	0.0509 (7)	0.0513 (7)	0.0028 (5)	0.0068 (5)	0.0054 (6)
N3	0.0474 (7)	0.0553 (8)	0.0508 (7)	0.0083 (6)	0.0139 (6)	0.0045 (6)
O1	0.0498 (6)	0.0726 (8)	0.0577 (7)	−0.0102 (5)	0.0184 (5)	−0.0137 (6)

C1—N1	1.3326 (19)	C11—H11	0.9300
C1—N2	1.3789 (19)	C12—C13	1.386 (3)
C1—C2	1.408 (2)	C12—H12	0.9300
C2—C3	1.364 (2)	C13—H13	0.9300
C2—H2	0.9300	C14—N3	1.272 (2)
C3—C4	1.415 (3)	C14—C15	1.451 (2)
C3—C21	1.500 (3)	C14—H14	0.9300
C4—C5	1.350 (3)	C15—C20	1.390 (2)
C4—H4	0.9300	C15—C16	1.398 (2)
C5—N2	1.375 (2)	C16—C17	1.374 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—N3	1.3818 (19)	C17—C18	1.395 (2)
C6—C7	1.384 (2)	C17—H17	0.9300
C6—N2	1.393 (2)	C18—O1	1.3491 (18)
C7—N1	1.3753 (19)	C18—C19	1.394 (2)
C7—C8	1.483 (2)	C19—C20	1.372 (2)
C8—C13	1.386 (2)	C19—H19	0.9300
C8—C9	1.389 (2)	C20—H20	0.9300
C9—C10	1.382 (2)	C21—H21A	0.9600
C9—H9	0.9300	C21—H21B	0.9600
C10—C11	1.372 (3)	C21—H21C	0.9600
C10—H10	0.9300	O1—H1	0.8200
C11—C12	1.371 (3)
N1—C1—N2	109.89 (13)	C12—C13—C8	120.56 (17)
N1—C1—C2	130.74 (14)	C12—C13—H13	119.7
N2—C1—C2	119.36 (14)	C8—C13—H13	119.7
C3—C2—C1	119.98 (16)	N3—C14—C15	124.79 (16)
C3—C2—H2	120.0	N3—C14—H14	117.6
C1—C2—H2	120.0	C15—C14—H14	117.6
C2—C3—C4	118.30 (16)	C20—C15—C16	117.76 (14)
C2—C3—C21	121.16 (19)	C20—C15—C14	118.96 (14)
C4—C3—C21	120.50 (18)	C16—C15—C14	123.28 (15)
C5—C4—C3	122.34 (16)	C17—C16—C15	121.05 (15)
C5—C4—H4	118.8	C17—C16—H16	119.5
C3—C4—H4	118.8	C15—C16—H16	119.5
C4—C5—N2	118.64 (17)	C16—C17—C18	120.29 (14)
C4—C5—H5	120.7	C16—C17—H17	119.9
N2—C5—H5	120.7	C18—C17—H17	119.9
N3—C6—C7	138.47 (15)	O1—C18—C19	117.56 (14)
N3—C6—N2	116.61 (13)	O1—C18—C17	123.18 (13)
C7—C6—N2	104.84 (12)	C19—C18—C17	119.25 (14)
N1—C7—C6	110.35 (13)	C20—C19—C18	119.66 (16)
N1—C7—C8	118.76 (12)	C20—C19—H19	120.2
C6—C7—C8	130.65 (13)	C18—C19—H19	120.2
C13—C8—C9	118.18 (15)	C19—C20—C15	121.97 (15)
C13—C8—C7	123.17 (14)	C19—C20—H20	119.0
C9—C8—C7	118.62 (14)	C15—C20—H20	119.0
C10—C9—C8	120.95 (17)	C3—C21—H21A	109.5
C10—C9—H9	119.5	C3—C21—H21B	109.5
C8—C9—H9	119.5	H21A—C21—H21B	109.5
C11—C10—C9	120.06 (18)	C3—C21—H21C	109.5
C11—C10—H10	120.0	H21A—C21—H21C	109.5
C9—C10—H10	120.0	H21B—C21—H21C	109.5
C12—C11—C10	119.85 (18)	C1—N1—C7	106.85 (12)
C12—C11—H11	120.1	C5—N2—C1	121.28 (14)
C10—C11—H11	120.1	C5—N2—C6	130.54 (14)
C11—C12—C13	120.37 (19)	C1—N2—C6	108.05 (12)
C11—C12—H12	119.8	C14—N3—C6	120.33 (14)
C13—C12—H12	119.8	C18—O1—H1	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···Cg1i	0.93	2.74	3.6705 (18)	175
O1—H1···N1ii	0.82	1.86	2.6699 (17)	170

Table 1

Hydrogen-bond geometry (, )

Cg1 is the centroid of the C15C20 ring.

DHA	DH	HA	D A	DHA
C13H13Cg1i	0.93	2.74	3.6705(18)	175
O1H1N1ii	0.82	1.86	2.6699(17)	170

Symmetry codes: (i) ; (ii) .