Crystal structure of 5-(5-chloro-2-hydroxy-benzo-yl)-2-(2-methyl-1H-indol-3-yl)nicotino-nitrile.

In the title compound, C22H14ClN3O2, the indole unit is essentially coplanar, with a maximum deviation of 0.035 Å for the C atom bearing the methyl group. The central pyridine ring is inclined to the indole ring system by 43.7 (1)°. The dihedral angle between the phenyl ring and the indole ring system is 15.7 (2)°, while that between the phenyl ring and the central pyridine ring is 46.3 (1)°. The mol-ecular structure is stabilized by an intra-molecular O-H⋯O hydrogen bonding, forming an S(6) ring motif. In the crystal, mol-ecules are linked via pairs of N-H⋯N hydrogen bonds, forming inversion dimers with an R 2 (2)(16) ring motif. The crystal structure also features C-H⋯π and π-π inter-actions [centroid-centroid separation = 3.688 (1) Å].

Related literature

For applications of acrylate derivatives, see: Barden (2011 ▸); Chai et al. (2006 ▸); Nieto et al. (2005 ▸); Singh et al. (2000 ▸); Andreani et al. (2001 ▸); Quetin-Leclercq (1994 ▸); Mukhopadhyay et al. (1981 ▸). For related crystal structures, see: Penthala et al. (2008 ▸). For graph-set analysis, see: Grell et al. (2000 ▸).

Experimental

Crystal data

C22H14ClN3O2

M = 387.81

Monoclinic

a = 16.0673 (15) Å

b = 7.4804 (7) Å

c = 17.0159 (15) Å

β = 113.452 (3)°

V = 1876.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.27 × 0.23 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.941, T max = 0.960

7690 measured reflections

3638 independent reflections

2447 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.170

S = 1.01

3638 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: APEX2 and SAINT (Bruker, 2008 ▸); data reduction: SAINT and XPREP (Bruker, 2008 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015018058/zp2018sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018058/zp2018Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015018058/zp2018Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015018058/zp2018fig1.tif

The mol­ecular structure of the title compound, with the atomic numbering scheme and displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

b . DOI: 10.1107/S2056989015018058/zp2018fig2.tif

O—H⋯O intra and N—H⋯N inter­mlecular inter­actions (dotted lines) in the crystal structure of the title compound. The crystal packing of the mol­ecules is viewed down the b axis.

CCDC reference: 1427861

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

C22H14ClN3O2	F(000) = 800
Mr = 387.81	Dx = 1.373 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2447 reflections
a = 16.0673 (15) Å	θ = 1.5–25.9°
b = 7.4804 (7) Å	µ = 0.23 mm−1
c = 17.0159 (15) Å	T = 293 K
β = 113.452 (3)°	Block, colourless
V = 1876.2 (3) Å3	0.27 × 0.23 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3638 independent reflections
Radiation source: fine-focus sealed tube	2447 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 0 pixels mm-1	θmax = 25.9°, θmin = 1.5°
ω and φ scan	h = −19→15
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −7→9
Tmin = 0.941, Tmax = 0.960	l = −20→20
7690 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0793P)2 + 1.1008P] where P = (Fo2 + 2Fc2)/3
3638 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.36 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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.6829 (2)	1.0448 (4)	0.2799 (2)	0.0475 (8)
C2	0.7315 (2)	1.0614 (5)	0.2278 (2)	0.0599 (9)
H2	0.7877	1.1176	0.2487	0.072*
C3	0.6961 (2)	0.9945 (5)	0.1459 (2)	0.0608 (9)
H3	0.7285	1.0055	0.1115	0.073*
C4	0.6122 (2)	0.9108 (5)	0.11432 (19)	0.0497 (8)
C5	0.56120 (19)	0.9038 (4)	0.16240 (17)	0.0416 (7)
H5	0.5036	0.8532	0.1393	0.050*
C6	0.59480 (17)	0.9718 (4)	0.24590 (17)	0.0377 (6)
C7	0.54170 (18)	0.9672 (4)	0.29877 (17)	0.0363 (6)
C8	0.44084 (17)	0.9513 (4)	0.26081 (16)	0.0327 (6)
C9	0.39945 (18)	0.8749 (4)	0.31059 (17)	0.0382 (6)
H9	0.4370	0.8306	0.3641	0.046*
C10	0.25482 (17)	0.9246 (3)	0.21050 (15)	0.0309 (6)
C11	0.29038 (17)	1.0110 (4)	0.15727 (15)	0.0328 (6)
C12	0.38420 (17)	1.0235 (4)	0.18271 (16)	0.0341 (6)
H12	0.4084	1.0794	0.1477	0.041*
C13	0.23147 (18)	1.0979 (4)	0.07944 (17)	0.0391 (7)
C14	0.15806 (17)	0.9068 (4)	0.19015 (16)	0.0331 (6)
C15	0.09024 (19)	0.8498 (4)	0.11465 (17)	0.0411 (7)
C16	0.02316 (18)	0.9066 (4)	0.20583 (19)	0.0424 (7)
C17	−0.0377 (2)	0.9216 (5)	0.2447 (3)	0.0577 (9)
H17	−0.0992	0.8991	0.2146	0.069*
C18	−0.0039 (2)	0.9706 (5)	0.3289 (3)	0.0625 (10)
H18	−0.0430	0.9798	0.3569	0.075*
C19	0.0883 (2)	1.0074 (4)	0.3739 (2)	0.0565 (9)
H19	0.1091	1.0423	0.4310	0.068*
C20	0.1487 (2)	0.9931 (4)	0.33560 (18)	0.0428 (7)
H20	0.2100	1.0177	0.3662	0.051*
C21	0.11658 (17)	0.9409 (3)	0.25004 (17)	0.0356 (6)
C22	0.0944 (2)	0.7734 (5)	0.03518 (18)	0.0563 (9)
H22A	0.0340	0.7473	−0.0054	0.084*
H22B	0.1296	0.6654	0.0490	0.084*
H22C	0.1221	0.8583	0.0108	0.084*
N1	0.31060 (14)	0.8602 (3)	0.28774 (13)	0.0373 (6)
N2	0.18555 (17)	1.1658 (4)	0.01731 (16)	0.0565 (7)
N3	0.00999 (15)	0.8531 (3)	0.12427 (16)	0.0481 (7)
H3A	−0.0417	0.8255	0.0849	0.058*
O1	0.72328 (15)	1.1053 (4)	0.36103 (15)	0.0673 (7)
H1	0.6973	1.0640	0.3898	0.101*
O2	0.58003 (13)	0.9826 (3)	0.37762 (12)	0.0537 (6)
Cl1	0.57239 (7)	0.81118 (15)	0.01424 (5)	0.0737 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0320 (16)	0.0497 (19)	0.0610 (19)	0.0020 (13)	0.0186 (14)	−0.0031 (15)
C2	0.0342 (18)	0.072 (2)	0.083 (2)	−0.0061 (16)	0.0330 (17)	−0.0059 (19)
C3	0.047 (2)	0.073 (2)	0.078 (2)	0.0088 (18)	0.0412 (19)	0.0046 (19)
C4	0.0410 (18)	0.061 (2)	0.0480 (17)	0.0175 (15)	0.0186 (14)	0.0019 (15)
C5	0.0311 (15)	0.0455 (17)	0.0471 (16)	0.0076 (13)	0.0143 (13)	0.0030 (13)
C6	0.0244 (14)	0.0397 (15)	0.0473 (16)	0.0027 (12)	0.0125 (12)	0.0018 (12)
C7	0.0276 (14)	0.0419 (16)	0.0384 (15)	0.0000 (12)	0.0121 (12)	0.0023 (12)
C8	0.0249 (13)	0.0380 (15)	0.0340 (13)	0.0006 (11)	0.0104 (11)	−0.0015 (11)
C9	0.0284 (14)	0.0479 (17)	0.0333 (14)	0.0022 (12)	0.0072 (11)	0.0052 (12)
C10	0.0264 (13)	0.0334 (14)	0.0303 (13)	−0.0008 (11)	0.0084 (11)	−0.0012 (10)
C11	0.0272 (14)	0.0383 (14)	0.0295 (13)	0.0006 (11)	0.0078 (11)	0.0003 (11)
C12	0.0287 (14)	0.0394 (15)	0.0357 (14)	−0.0006 (11)	0.0143 (11)	0.0017 (11)
C13	0.0300 (15)	0.0510 (17)	0.0354 (15)	−0.0029 (13)	0.0119 (12)	0.0032 (13)
C14	0.0257 (14)	0.0356 (14)	0.0356 (14)	−0.0015 (11)	0.0098 (11)	0.0032 (11)
C15	0.0326 (16)	0.0429 (16)	0.0404 (15)	−0.0040 (12)	0.0067 (12)	0.0056 (12)
C16	0.0290 (15)	0.0383 (16)	0.0590 (18)	0.0020 (12)	0.0164 (13)	0.0113 (13)
C17	0.0327 (17)	0.054 (2)	0.091 (3)	0.0040 (14)	0.0296 (18)	0.0153 (18)
C18	0.057 (2)	0.057 (2)	0.096 (3)	0.0111 (17)	0.053 (2)	0.0110 (19)
C19	0.067 (2)	0.0496 (19)	0.066 (2)	0.0045 (17)	0.0405 (18)	0.0023 (16)
C20	0.0400 (17)	0.0411 (16)	0.0504 (17)	−0.0008 (13)	0.0213 (14)	0.0007 (13)
C21	0.0255 (13)	0.0325 (14)	0.0478 (16)	0.0006 (11)	0.0134 (12)	0.0066 (12)
C22	0.058 (2)	0.058 (2)	0.0391 (16)	−0.0120 (16)	0.0050 (15)	−0.0068 (14)
N1	0.0286 (12)	0.0456 (14)	0.0353 (12)	−0.0018 (10)	0.0102 (10)	0.0055 (10)
N2	0.0393 (15)	0.074 (2)	0.0440 (15)	−0.0056 (13)	0.0042 (12)	0.0157 (14)
N3	0.0230 (13)	0.0574 (16)	0.0514 (15)	−0.0069 (11)	0.0018 (11)	0.0063 (12)
O1	0.0365 (13)	0.0949 (19)	0.0668 (15)	−0.0177 (12)	0.0167 (11)	−0.0186 (14)
O2	0.0325 (11)	0.0819 (16)	0.0400 (11)	−0.0051 (10)	0.0074 (9)	0.0039 (11)
Cl1	0.0757 (7)	0.0959 (8)	0.0522 (5)	0.0250 (5)	0.0283 (5)	−0.0047 (5)

C1—O1	1.349 (4)	C12—H12	0.9300
C1—C2	1.399 (4)	C13—N2	1.140 (3)
C1—C6	1.409 (4)	C14—C15	1.380 (4)
C2—C3	1.373 (5)	C14—C21	1.445 (4)
C2—H2	0.9300	C15—N3	1.363 (4)
C3—C4	1.386 (5)	C15—C22	1.494 (4)
C3—H3	0.9300	C16—N3	1.377 (4)
C4—C5	1.370 (4)	C16—C17	1.386 (4)
C4—Cl1	1.731 (3)	C16—C21	1.409 (4)
C5—C6	1.399 (4)	C17—C18	1.365 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—C7	1.466 (4)	C18—C19	1.398 (5)
C7—O2	1.239 (3)	C18—H18	0.9300
C7—C8	1.491 (4)	C19—C20	1.372 (4)
C8—C12	1.387 (4)	C19—H19	0.9300
C8—C9	1.391 (4)	C20—C21	1.393 (4)
C9—N1	1.327 (3)	C20—H20	0.9300
C9—H9	0.9300	C22—H22A	0.9600
C10—N1	1.351 (3)	C22—H22B	0.9600
C10—C11	1.405 (4)	C22—H22C	0.9600
C10—C14	1.458 (3)	N3—H3A	0.8600
C11—C12	1.396 (3)	O1—H1	0.8200
C11—C13	1.441 (4)
O1—C1—C2	117.2 (3)	N2—C13—C11	179.1 (3)
O1—C1—C6	123.0 (3)	C15—C14—C21	107.2 (2)
C2—C1—C6	119.8 (3)	C15—C14—C10	128.4 (2)
C3—C2—C1	120.0 (3)	C21—C14—C10	124.3 (2)
C3—C2—H2	120.0	N3—C15—C14	108.5 (3)
C1—C2—H2	120.0	N3—C15—C22	120.0 (3)
C2—C3—C4	120.3 (3)	C14—C15—C22	131.1 (3)
C2—C3—H3	119.9	N3—C16—C17	130.5 (3)
C4—C3—H3	119.9	N3—C16—C21	107.1 (2)
C5—C4—C3	120.4 (3)	C17—C16—C21	122.3 (3)
C5—C4—Cl1	119.8 (3)	C18—C17—C16	117.4 (3)
C3—C4—Cl1	119.8 (2)	C18—C17—H17	121.3
C4—C5—C6	120.8 (3)	C16—C17—H17	121.3
C4—C5—H5	119.6	C17—C18—C19	121.3 (3)
C6—C5—H5	119.6	C17—C18—H18	119.3
C5—C6—C1	118.4 (3)	C19—C18—H18	119.3
C5—C6—C7	122.1 (2)	C20—C19—C18	121.4 (3)
C1—C6—C7	119.5 (3)	C20—C19—H19	119.3
O2—C7—C6	120.2 (2)	C18—C19—H19	119.3
O2—C7—C8	117.5 (2)	C19—C20—C21	118.7 (3)
C6—C7—C8	122.2 (2)	C19—C20—H20	120.6
C12—C8—C9	116.9 (2)	C21—C20—H20	120.6
C12—C8—C7	124.7 (2)	C20—C21—C16	118.8 (3)
C9—C8—C7	118.0 (2)	C20—C21—C14	134.7 (2)
N1—C9—C8	125.1 (2)	C16—C21—C14	106.5 (2)
N1—C9—H9	117.4	C15—C22—H22A	109.5
C8—C9—H9	117.4	C15—C22—H22B	109.5
N1—C10—C11	120.6 (2)	H22A—C22—H22B	109.5
N1—C10—C14	115.5 (2)	C15—C22—H22C	109.5
C11—C10—C14	123.9 (2)	H22A—C22—H22C	109.5
C12—C11—C10	119.8 (2)	H22B—C22—H22C	109.5
C12—C11—C13	119.2 (2)	C9—N1—C10	118.4 (2)
C10—C11—C13	120.9 (2)	C15—N3—C16	110.7 (2)
C8—C12—C11	119.1 (2)	C15—N3—H3A	124.7
C8—C12—H12	120.4	C16—N3—H3A	124.7
C11—C12—H12	120.4	C1—O1—H1	109.5
O1—C1—C2—C3	176.8 (3)	C10—C11—C13—N2	−138 (22)
C6—C1—C2—C3	−4.8 (5)	N1—C10—C14—C15	−135.0 (3)
C1—C2—C3—C4	0.1 (5)	C11—C10—C14—C15	48.5 (4)
C2—C3—C4—C5	4.1 (5)	N1—C10—C14—C21	42.3 (3)
C2—C3—C4—Cl1	−174.8 (3)	C11—C10—C14—C21	−134.3 (3)
C3—C4—C5—C6	−3.6 (5)	C21—C14—C15—N3	2.0 (3)
Cl1—C4—C5—C6	175.3 (2)	C10—C14—C15—N3	179.6 (2)
C4—C5—C6—C1	−1.1 (4)	C21—C14—C15—C22	−170.9 (3)
C4—C5—C6—C7	179.7 (3)	C10—C14—C15—C22	6.7 (5)
O1—C1—C6—C5	−176.5 (3)	N3—C16—C17—C18	176.8 (3)
C2—C1—C6—C5	5.3 (4)	C21—C16—C17—C18	−0.3 (4)
O1—C1—C6—C7	2.8 (5)	C16—C17—C18—C19	1.1 (5)
C2—C1—C6—C7	−175.4 (3)	C17—C18—C19—C20	−1.0 (5)
C5—C6—C7—O2	160.6 (3)	C18—C19—C20—C21	0.1 (4)
C1—C6—C7—O2	−18.6 (4)	C19—C20—C21—C16	0.6 (4)
C5—C6—C7—C8	−21.8 (4)	C19—C20—C21—C14	−177.9 (3)
C1—C6—C7—C8	158.9 (3)	N3—C16—C21—C20	−178.3 (2)
O2—C7—C8—C12	144.3 (3)	C17—C16—C21—C20	−0.5 (4)
C6—C7—C8—C12	−33.3 (4)	N3—C16—C21—C14	0.6 (3)
O2—C7—C8—C9	−28.8 (4)	C17—C16—C21—C14	178.4 (3)
C6—C7—C8—C9	153.6 (3)	C15—C14—C21—C20	177.0 (3)
C12—C8—C9—N1	2.6 (4)	C10—C14—C21—C20	−0.7 (5)
C7—C8—C9—N1	176.2 (2)	C15—C14—C21—C16	−1.6 (3)
N1—C10—C11—C12	2.8 (4)	C10—C14—C21—C16	−179.4 (2)
C14—C10—C11—C12	179.2 (2)	C8—C9—N1—C10	−0.4 (4)
N1—C10—C11—C13	−172.8 (2)	C11—C10—N1—C9	−2.3 (4)
C14—C10—C11—C13	3.5 (4)	C14—C10—N1—C9	−179.0 (2)
C9—C8—C12—C11	−2.0 (4)	C14—C15—N3—C16	−1.7 (3)
C7—C8—C12—C11	−175.1 (2)	C22—C15—N3—C16	172.1 (3)
C10—C11—C12—C8	−0.5 (4)	C17—C16—N3—C15	−176.9 (3)
C13—C11—C12—C8	175.2 (2)	C21—C16—N3—C15	0.6 (3)
C12—C11—C13—N2	47 (22)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.91	2.596 (3)	140
N3—H3A···N2i	0.86	2.27	3.110 (4)	164
C2—H2···Cg3ii	0.90	2.93	3.656 (4)	136
C12—H12···Cg4iii	0.93	2.99	3.361 (4)	106

Table 1

Hydrogen-bond geometry (, )

Cg3 and Cg4 are the centroids of the C1C6 and C16C21 rings, respectively.

DHA	DH	HA	D A	DHA
O1H1O2	0.82	1.91	2.596(3)	140
N3H3AN2i	0.86	2.27	3.110(4)	164
C2H2Cg3ii	0.90	2.93	3.656(4)	136
C12H12Cg4iii	0.93	2.99	3.361(4)	106

Symmetry codes: (i) ; (ii) ; (iii) .