Crystal structure of 7-{[bis­(pyridin-2-ylmeth­yl)amino]­meth­yl}-5-chloro­quinolin-8-ol

In the title compound, there is an intra­molecular O—H...N hydrogen bond forming an S(9) ring motif. In the crystal, mol­ecules are linked via C—H...O hydrogen bonds forming inversion dimers with an R₄⁴(10) ring motif. The dimers are linked by C—H...N hydrogen bonds, forming ribbons along [01-1].

Computing details

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO (Rigaku, 2006); data reduction: RAPID-AUTO (Rigaku, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: CrystalStructure (Rigaku, 2014).

7-{[Bis(pyridin-2-ylmethyl)amino]methyl}-5-chloroquinolin-8-ol

Crystal data

C22H19ClN4O	Z = 2
Mr = 390.86	F(000) = 408.00
Triclinic, P1	Dx = 1.368 Mg m^−3
a = 8.3170 (5) Å	Mo Kα radiation, λ = 0.71075 Å
b = 11.5993 (7) Å	Cell parameters from 5840 reflections
c = 11.6135 (6) Å	θ = 3.1–27.4°
α = 116.8473 (13)°	µ = 0.22 mm^−1
β = 105.2809 (13)°	T = 296 K
γ = 92.0110 (17)°	Block, yellow
V = 948.68 (10) Å^3	0.30 × 0.20 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	2329 reflections with F^2 > 2.0σ(F^2)
Detector resolution: 10.000 pixels mm^-1	Rint = 0.023
ω scans	θmax = 27.4°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.769, Tmax = 0.978	k = −15→15
9412 measured reflections	l = −14→15
4293 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0488P)^2 + 0.1777P] where P = (Fo^2 + 2Fc^2)/3
4293 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.24 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Geometry. Refinement was performed 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 sigma(F²) is used only for calculating R-factor (gt).

Refinement. Refinement was performed 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
Cl1	0.20020 (9)	0.40251 (6)	0.58501 (6)	0.0724 (2)
O2	0.3787 (2)	0.45209 (15)	0.14798 (14)	0.0563 (4)
N3	0.3767 (2)	0.22221 (18)	0.14868 (17)	0.0560 (5)
N4	0.1525 (2)	0.72637 (15)	0.33905 (15)	0.0432 (4)
N5	0.2432 (2)	0.61932 (17)	0.06500 (16)	0.0500 (4)
N6	0.2990 (2)	1.07071 (18)	0.58796 (17)	0.0562 (5)
C7	0.3408 (2)	0.4468 (2)	0.25274 (18)	0.0444 (5)
C8	0.3075 (2)	0.5531 (2)	0.35655 (19)	0.0440 (5)
C9	0.2637 (3)	0.5344 (2)	0.45812 (19)	0.0488 (5)
C10	0.2564 (3)	0.4177 (2)	0.45746 (19)	0.0474 (5)
C11	0.2949 (2)	0.3074 (2)	0.35528 (18)	0.0451 (5)
C12	0.2940 (3)	0.1827 (2)	0.3486 (2)	0.0546 (5)
C13	0.3335 (3)	0.0841 (2)	0.2454 (2)	0.0642 (6)
C14	0.3733 (3)	0.1088 (2)	0.1483 (2)	0.0645 (6)
C15	0.3387 (2)	0.3236 (2)	0.25179 (18)	0.0439 (5)
C16	0.3190 (3)	0.6889 (2)	0.3710 (2)	0.0469 (5)
C17	0.0484 (3)	0.6472 (2)	0.19651 (18)	0.0453 (5)
C18	0.1068 (3)	0.67040 (19)	0.09391 (18)	0.0440 (5)
C19	0.0266 (3)	0.7400 (2)	0.0336 (2)	0.0542 (5)
C20	0.0860 (3)	0.7593 (3)	−0.0582 (2)	0.0646 (6)
C21	0.2264 (3)	0.7087 (3)	−0.0865 (2)	0.0637 (6)
C22	0.2999 (3)	0.6399 (2)	−0.0238 (2)	0.0577 (6)
C23	0.1681 (3)	0.8665 (2)	0.3842 (2)	0.0549 (6)
C24	0.2147 (3)	0.9495 (2)	0.53687 (19)	0.0463 (5)
C25	0.1679 (3)	0.9048 (2)	0.6174 (2)	0.0563 (6)
C26	0.2149 (3)	0.9865 (2)	0.7564 (2)	0.0600 (6)
C27	0.3044 (3)	1.1103 (2)	0.8101 (2)	0.0570 (6)
C28	0.3404 (3)	1.1481 (2)	0.7224 (2)	0.0614 (6)
H2	0.329 (3)	0.526 (3)	0.129 (3)	0.098 (9)*
H9	0.23914	0.60515	0.52745	0.0585*
H12	0.26668	0.16817	0.41415	0.0655*
H13	0.33386	0.00152	0.23959	0.0771*
H14	0.39931	0.0399	0.07819	0.0774*
H16A	0.38532	0.7515	0.46354	0.0563*
H16B	0.37804	0.69349	0.31109	0.0563*
H17A	−0.06633	0.66426	0.18846	0.0544*
H17B	0.04458	0.55522	0.17233	0.0544*
H19	−0.06765	0.77418	0.05442	0.0651*
H20	0.03192	0.80564	−0.10001	0.0776*
H21	0.27022	0.72111	−0.14678	0.0764*
H22	0.39441	0.60539	−0.04348	0.0692*
H23A	0.06141	0.88388	0.34197	0.0659*
H23B	0.25394	0.89247	0.35362	0.0659*
H25	0.10548	0.82092	0.57873	0.0676*
H26	0.18619	0.95777	0.81246	0.0720*
H27	0.33951	1.16686	0.90321	0.0684*
H28	0.39751	1.2333	0.75867	0.0737*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0990 (5)	0.0762 (4)	0.0553 (4)	0.0150 (4)	0.0451 (3)	0.0312 (3)
O2	0.0698 (10)	0.0665 (10)	0.0499 (8)	0.0272 (8)	0.0355 (8)	0.0321 (8)
N3	0.0734 (13)	0.0579 (12)	0.0446 (10)	0.0263 (10)	0.0282 (9)	0.0247 (9)
N4	0.0515 (10)	0.0396 (9)	0.0336 (8)	0.0077 (8)	0.0159 (7)	0.0123 (8)
N5	0.0525 (11)	0.0546 (11)	0.0389 (9)	0.0099 (9)	0.0180 (8)	0.0169 (9)
N6	0.0747 (13)	0.0454 (11)	0.0413 (10)	0.0005 (9)	0.0243 (9)	0.0122 (9)
C7	0.0422 (11)	0.0567 (13)	0.0350 (10)	0.0116 (10)	0.0153 (9)	0.0206 (10)
C8	0.0415 (11)	0.0493 (12)	0.0364 (10)	0.0063 (9)	0.0121 (8)	0.0167 (9)
C9	0.0504 (12)	0.0543 (13)	0.0336 (10)	0.0101 (10)	0.0165 (9)	0.0125 (10)
C10	0.0511 (12)	0.0551 (14)	0.0363 (10)	0.0075 (10)	0.0161 (9)	0.0208 (10)
C11	0.0416 (11)	0.0543 (13)	0.0347 (10)	0.0079 (10)	0.0108 (8)	0.0181 (10)
C12	0.0622 (14)	0.0598 (15)	0.0463 (12)	0.0117 (11)	0.0188 (11)	0.0281 (12)
C13	0.0846 (18)	0.0573 (15)	0.0593 (14)	0.0216 (13)	0.0287 (13)	0.0308 (13)
C14	0.0896 (18)	0.0579 (15)	0.0530 (13)	0.0316 (13)	0.0333 (13)	0.0250 (12)
C15	0.0437 (11)	0.0522 (13)	0.0352 (10)	0.0132 (10)	0.0143 (9)	0.0192 (10)
C16	0.0478 (12)	0.0478 (12)	0.0364 (10)	0.0022 (10)	0.0140 (9)	0.0129 (9)
C17	0.0450 (11)	0.0461 (12)	0.0361 (10)	0.0051 (9)	0.0135 (9)	0.0122 (9)
C18	0.0441 (11)	0.0431 (11)	0.0305 (9)	0.0027 (9)	0.0095 (8)	0.0075 (9)
C19	0.0544 (13)	0.0585 (14)	0.0441 (11)	0.0130 (11)	0.0146 (10)	0.0201 (11)
C20	0.0732 (17)	0.0701 (16)	0.0520 (13)	0.0108 (13)	0.0155 (12)	0.0326 (13)
C21	0.0717 (16)	0.0737 (17)	0.0466 (12)	0.0020 (13)	0.0214 (12)	0.0288 (13)
C22	0.0566 (14)	0.0681 (15)	0.0446 (12)	0.0090 (12)	0.0230 (10)	0.0203 (12)
C23	0.0801 (16)	0.0432 (13)	0.0376 (11)	0.0105 (11)	0.0217 (11)	0.0144 (10)
C24	0.0585 (13)	0.0413 (12)	0.0363 (10)	0.0111 (10)	0.0191 (9)	0.0137 (9)
C25	0.0781 (16)	0.0463 (13)	0.0465 (12)	0.0078 (11)	0.0280 (11)	0.0193 (11)
C26	0.0820 (17)	0.0648 (16)	0.0449 (12)	0.0187 (13)	0.0331 (12)	0.0283 (12)
C27	0.0613 (14)	0.0620 (15)	0.0355 (11)	0.0108 (12)	0.0189 (10)	0.0113 (11)
C28	0.0685 (16)	0.0535 (14)	0.0442 (12)	−0.0039 (12)	0.0215 (11)	0.0076 (11)

Geometric parameters (Å, º)

Cl1—C10	1.743 (3)	C21—C22	1.366 (4)
O2—C7	1.361 (3)	C23—C24	1.514 (3)
N3—C14	1.313 (4)	C24—C25	1.382 (4)
N3—C15	1.368 (3)	C25—C26	1.384 (3)
N4—C16	1.470 (3)	C26—C27	1.369 (4)
N4—C17	1.466 (2)	C27—C28	1.370 (4)
N4—C23	1.454 (3)	O2—H2	1.04 (3)
N5—C18	1.349 (3)	C9—H9	0.930
N5—C22	1.347 (4)	C12—H12	0.930
N6—C24	1.334 (3)	C13—H13	0.930
N6—C28	1.338 (3)	C14—H14	0.930
C7—C8	1.381 (3)	C16—H16A	0.970
C7—C15	1.424 (4)	C16—H16B	0.970
C8—C9	1.422 (4)	C17—H17A	0.970
C8—C16	1.504 (3)	C17—H17B	0.970
C9—C10	1.349 (4)	C19—H19	0.930
C10—C11	1.416 (3)	C20—H20	0.930
C11—C12	1.412 (4)	C21—H21	0.930
C11—C15	1.429 (4)	C22—H22	0.930
C12—C13	1.359 (3)	C23—H23A	0.970
C13—C14	1.394 (5)	C23—H23B	0.970
C17—C18	1.521 (4)	C25—H25	0.930
C18—C19	1.375 (4)	C26—H26	0.930
C19—C20	1.384 (4)	C27—H27	0.930
C20—C21	1.376 (4)	C28—H28	0.930
C14—N3—C15	117.7 (2)	N6—C28—C27	124.4 (2)
C16—N4—C17	113.69 (15)	C7—O2—H2	112.4 (18)
C16—N4—C23	111.51 (16)	C8—C9—H9	118.825
C17—N4—C23	112.33 (18)	C10—C9—H9	118.839
C18—N5—C22	117.9 (2)	C11—C12—H12	120.293
C24—N6—C28	117.2 (2)	C13—C12—H12	120.294
O2—C7—C8	123.5 (2)	C12—C13—H13	120.515
O2—C7—C15	116.17 (17)	C14—C13—H13	120.514
C8—C7—C15	120.4 (2)	N3—C14—H14	117.649
C7—C8—C9	118.4 (2)	C13—C14—H14	117.655
C7—C8—C16	124.0 (2)	N4—C16—H16A	108.956
C9—C8—C16	117.66 (18)	N4—C16—H16B	108.959
C8—C9—C10	122.34 (19)	C8—C16—H16A	108.959
Cl1—C10—C9	119.55 (16)	C8—C16—H16B	108.962
Cl1—C10—C11	119.4 (2)	H16A—C16—H16B	107.759
C9—C10—C11	121.1 (2)	N4—C17—H17A	108.296
C10—C11—C12	124.8 (2)	N4—C17—H17B	108.295
C10—C11—C15	117.6 (2)	C18—C17—H17A	108.301
C12—C11—C15	117.59 (18)	C18—C17—H17B	108.301
C11—C12—C13	119.4 (3)	H17A—C17—H17B	107.402
C12—C13—C14	119.0 (3)	C18—C19—H19	119.991
N3—C14—C13	124.7 (2)	C20—C19—H19	119.983
N3—C15—C7	118.2 (2)	C19—C20—H20	120.561
N3—C15—C11	121.6 (2)	C21—C20—H20	120.563
C7—C15—C11	120.18 (18)	C20—C21—H21	120.849
N4—C16—C8	113.11 (17)	C22—C21—H21	120.854
N4—C17—C18	115.94 (17)	N5—C22—H22	118.151
N5—C18—C17	116.4 (2)	C21—C22—H22	118.151
N5—C18—C19	121.2 (2)	N4—C23—H23A	108.897
C17—C18—C19	122.4 (2)	N4—C23—H23B	108.899
C18—C19—C20	120.0 (2)	C24—C23—H23A	108.892
C19—C20—C21	118.9 (3)	C24—C23—H23B	108.896
C20—C21—C22	118.3 (3)	H23A—C23—H23B	107.725
N5—C22—C21	123.7 (2)	C24—C25—H25	120.400
N4—C23—C24	113.4 (2)	C26—C25—H25	120.399
N6—C24—C23	115.3 (2)	C25—C26—H26	120.492
N6—C24—C25	122.17 (18)	C27—C26—H26	120.490
C23—C24—C25	122.53 (19)	C26—C27—H27	121.022
C24—C25—C26	119.2 (2)	C28—C27—H27	121.032
C25—C26—C27	119.0 (3)	N6—C28—H28	117.816
C26—C27—C28	117.95 (19)	C27—C28—H28	117.809
C14—N3—C15—C7	−179.57 (17)	C8—C9—C10—C11	0.9 (3)
C14—N3—C15—C11	−0.6 (3)	Cl1—C10—C11—C12	−1.0 (2)
C15—N3—C14—C13	0.1 (3)	Cl1—C10—C11—C15	179.37 (11)
C16—N4—C17—C18	−70.7 (2)	C9—C10—C11—C12	178.57 (16)
C17—N4—C16—C8	−65.3 (2)	C9—C10—C11—C15	−1.1 (3)
C16—N4—C23—C24	−72.8 (2)	C10—C11—C12—C13	−179.91 (16)
C23—N4—C16—C8	166.49 (16)	C10—C11—C15—N3	−179.63 (15)
C17—N4—C23—C24	158.23 (17)	C10—C11—C15—C7	−0.7 (2)
C23—N4—C17—C18	57.1 (2)	C12—C11—C15—N3	0.7 (2)
C18—N5—C22—C21	−0.4 (2)	C12—C11—C15—C7	179.66 (15)
C22—N5—C18—C17	−178.93 (13)	C15—C11—C12—C13	−0.3 (3)
C22—N5—C18—C19	0.8 (2)	C11—C12—C13—C14	−0.2 (3)
C24—N6—C28—C27	1.1 (3)	C12—C13—C14—N3	0.4 (4)
C28—N6—C24—C23	178.99 (18)	N4—C17—C18—N5	75.0 (2)
C28—N6—C24—C25	1.3 (3)	N4—C17—C18—C19	−104.73 (19)
O2—C7—C8—C9	177.87 (14)	N5—C18—C19—C20	−0.3 (2)
O2—C7—C8—C16	−3.8 (3)	C17—C18—C19—C20	179.38 (13)
O2—C7—C15—N3	1.0 (2)	C18—C19—C20—C21	−0.5 (3)
O2—C7—C15—C11	−177.99 (13)	C19—C20—C21—C22	0.9 (3)
C8—C7—C15—N3	−178.35 (15)	C20—C21—C22—N5	−0.4 (3)
C8—C7—C15—C11	2.7 (2)	N4—C23—C24—N6	152.46 (19)
C15—C7—C8—C9	−2.8 (2)	N4—C23—C24—C25	−29.9 (3)
C15—C7—C8—C16	175.54 (14)	N6—C24—C25—C26	−2.4 (4)
C7—C8—C9—C10	1.1 (3)	C23—C24—C25—C26	−179.9 (2)
C7—C8—C16—N4	107.8 (2)	C24—C25—C26—C27	1.0 (4)
C9—C8—C16—N4	−73.8 (2)	C25—C26—C27—C28	1.2 (4)
C16—C8—C9—C10	−177.37 (15)	C26—C27—C28—N6	−2.3 (4)
C8—C9—C10—Cl1	−179.55 (14)

Hydrogen-bond geometry (Å, º)

Cg2 and Cg3 are the centroids of rings N5/C18–C22 and N6/C24–C28, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N5	1.04 (3)	1.66 (4)	2.689 (3)	168 (2)
C22—H22···O2^i	0.93	2.46	3.348 (3)	160
C27—H27···N3^ii	0.93	2.55	3.406 (3)	153
C17—H17b···Cg2^iii	0.97	2.79	3.599 (3)	141
C23—H23A···Cg3^iv	0.97	2.86	3.770 (3)	156

Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z+1; (iii) −x, −y+1, −z; (iv) −x, −y+2, −z+1.