3-{[Bis(pyridin-2-ylmeth-yl)amino]-meth-yl}-2-hy-droxy-5-methyl-benz-aldehyde.

In the title compound, C(21)H(21)N(3)O(2), the pyridine rings and the benzene ring lie in a propeller arrangement around the central tertiary amine N atom. The dihedral angles formed by the benzene ring with the pyridine rings are 61.0 (3) and 49.6 (3)°, while the dihedral angle between the pyridine rings is 69.7 (3)°. The mol-ecular conformation is stabilized by intramolecular bifurcated O-H⋯N hydrogen bonds. In the crystal, inversion dimers are formed via pairs of C-H⋯N hydrogen bonds.

Related literature

For general background to unsymmetric phenolate compounds, see: Lambert et al. (1997 ▶); Dubois, Xiang et al. (2003 ▶); Dubois, Caspar et al. (2003 ▶); Carlsson et al. (2004 ▶). For the syntheses and structures of related compounds, see: Chirakul et al. (2000 ▶); Abe et al. (2006 ▶); Bortoluzzi et al. (2007 ▶); Koval, Huisman, Stassen, Gamez, Lutz, Spek & Reedijk (2004 ▶); Koval, Huisman, Stassen, Gamez, Lutz, Spek, Pursche et al. (2004 ▶); Koval et al. (2007 ▶); Zhu et al. (2007 ▶). For the synthesis of the title compound, see: Lambert et al. (1997 ▶); Koval et al. (2003 ▶).

Experimental

Crystal data

C21H21N3O2

M = 347.41

Triclinic,

a = 8.479 (3) Å

b = 9.007 (3) Å

c = 12.734 (4) Å

α = 107.565 (4)°

β = 94.068 (4)°

γ = 99.092 (4)°

V = 908.2 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.16 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.987, T max = 0.993

6434 measured reflections

3159 independent reflections

2612 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.117

S = 1.06

3159 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019940/rz2747sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019940/rz2747Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019940/rz2747Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H21N3O2	Z = 2
Mr = 347.41	F(000) = 368
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.479 (3) Å	Cell parameters from 285 reflections
b = 9.007 (3) Å	θ = 1.7–26.9°
c = 12.734 (4) Å	µ = 0.08 mm−1
α = 107.565 (4)°	T = 296 K
β = 94.068 (4)°	Prism, colourless
γ = 99.092 (4)°	0.16 × 0.12 × 0.08 mm
V = 908.2 (5) Å3

Bruker APEXII CCD diffractometer	3159 independent reflections
Radiation source: fine-focus sealed tube	2612 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
ω scans	θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −10→9
Tmin = 0.987, Tmax = 0.993	k = −10→9
6434 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.1506P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
3159 reflections	Δρmax = 0.28 e Å−3
240 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (4)

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
O1	0.30347 (14)	0.24261 (15)	0.70069 (11)	0.0612 (4)
O2	0.2793 (2)	0.4303 (2)	0.45307 (13)	0.0963 (5)
N1	0.08654 (17)	0.36504 (16)	1.11217 (10)	0.0500 (3)
N2	0.44036 (16)	0.04369 (16)	0.84649 (12)	0.0556 (4)
N3	0.13178 (14)	0.13408 (13)	0.85047 (9)	0.0373 (3)
C1	0.1725 (2)	0.4744 (2)	1.20326 (14)	0.0619 (5)
H1A	0.1422	0.4755	1.2722	0.074*
C2	0.3018 (2)	0.5841 (2)	1.20004 (17)	0.0672 (5)
H2A	0.3586	0.6568	1.2652	0.081*
C3	0.3457 (2)	0.5845 (2)	1.09924 (19)	0.0677 (5)
H3A	0.4331	0.6578	1.0944	0.081*
C4	0.2591 (2)	0.47535 (19)	1.00495 (15)	0.0544 (4)
H4A	0.2865	0.4747	0.9354	0.065*
C5	0.13093 (17)	0.36626 (16)	1.01410 (12)	0.0386 (3)
C6	0.5620 (2)	−0.0253 (2)	0.80858 (17)	0.0649 (5)
H6A	0.6501	0.0376	0.7938	0.078*
C7	0.5662 (2)	−0.1817 (2)	0.79005 (16)	0.0644 (5)
H7A	0.6543	−0.2242	0.7636	0.077*
C8	0.4367 (3)	−0.2741 (2)	0.81160 (18)	0.0719 (6)
H8A	0.4350	−0.3813	0.8001	0.086*
C9	0.3086 (2)	−0.2069 (2)	0.85051 (16)	0.0599 (5)
H9A	0.2190	−0.2683	0.8648	0.072*
C10	0.31508 (17)	−0.04723 (17)	0.86807 (12)	0.0400 (3)
C11	0.03455 (17)	0.24405 (18)	0.91278 (12)	0.0414 (3)
H11A	−0.0550	0.1841	0.9350	0.050*
H11B	−0.0093	0.2971	0.8647	0.050*
C12	0.18157 (18)	0.03443 (18)	0.91383 (12)	0.0433 (4)
H12A	0.0896	−0.0450	0.9134	0.052*
H12B	0.2170	0.0996	0.9903	0.052*
C13	0.04151 (18)	0.03472 (17)	0.74274 (12)	0.0426 (4)
H13A	−0.0639	−0.0127	0.7545	0.051*
H13B	0.0976	−0.0504	0.7096	0.051*
C14	0.02146 (18)	0.12748 (17)	0.66384 (11)	0.0417 (4)
C15	−0.1264 (2)	0.11424 (19)	0.60476 (12)	0.0488 (4)
H15A	−0.2157	0.0511	0.6179	0.059*
C16	−0.1472 (2)	0.1916 (2)	0.52628 (13)	0.0540 (4)
C17	−0.0125 (2)	0.28009 (19)	0.50600 (13)	0.0548 (4)
H17A	−0.0229	0.3306	0.4527	0.066*
C18	0.1394 (2)	0.29671 (18)	0.56266 (12)	0.0496 (4)
C19	0.15547 (19)	0.22339 (18)	0.64412 (12)	0.0447 (4)
C20	−0.3128 (3)	0.1731 (3)	0.46591 (17)	0.0776 (6)
H20A	−0.3064	0.2332	0.4151	0.116*
H20B	−0.3843	0.2111	0.5187	0.116*
H20C	−0.3529	0.0631	0.4256	0.116*
C21	0.2815 (3)	0.3831 (2)	0.53231 (16)	0.0656 (5)
H21A	0.3792	0.4027	0.5768	0.079*
H1B	0.286 (3)	0.207 (3)	0.762 (2)	0.088 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0500 (7)	0.0767 (9)	0.0618 (8)	0.0016 (6)	−0.0033 (6)	0.0369 (7)
O2	0.1206 (13)	0.1079 (12)	0.0805 (10)	0.0155 (10)	0.0190 (9)	0.0608 (10)
N1	0.0583 (8)	0.0525 (8)	0.0402 (7)	0.0139 (6)	0.0080 (6)	0.0143 (6)
N2	0.0447 (8)	0.0503 (8)	0.0726 (9)	0.0084 (6)	0.0122 (7)	0.0196 (7)
N3	0.0409 (7)	0.0406 (7)	0.0325 (6)	0.0132 (5)	0.0043 (5)	0.0118 (5)
C1	0.0779 (13)	0.0663 (12)	0.0402 (9)	0.0278 (10)	0.0011 (8)	0.0092 (8)
C2	0.0591 (12)	0.0548 (11)	0.0687 (13)	0.0207 (9)	−0.0150 (9)	−0.0082 (9)
C3	0.0483 (10)	0.0476 (10)	0.0942 (15)	0.0050 (8)	0.0077 (10)	0.0055 (10)
C4	0.0536 (10)	0.0487 (9)	0.0611 (10)	0.0094 (8)	0.0163 (8)	0.0157 (8)
C5	0.0392 (8)	0.0392 (8)	0.0411 (8)	0.0155 (6)	0.0067 (6)	0.0139 (6)
C6	0.0413 (9)	0.0742 (12)	0.0825 (13)	0.0128 (9)	0.0133 (9)	0.0277 (10)
C7	0.0553 (11)	0.0843 (14)	0.0662 (11)	0.0374 (10)	0.0134 (9)	0.0288 (10)
C8	0.0888 (14)	0.0615 (11)	0.0865 (14)	0.0411 (11)	0.0302 (12)	0.0363 (11)
C9	0.0681 (12)	0.0514 (10)	0.0752 (12)	0.0212 (9)	0.0267 (9)	0.0330 (9)
C10	0.0412 (8)	0.0450 (8)	0.0369 (7)	0.0104 (6)	0.0020 (6)	0.0172 (6)
C11	0.0396 (8)	0.0472 (8)	0.0389 (8)	0.0139 (6)	0.0059 (6)	0.0126 (6)
C12	0.0486 (9)	0.0467 (8)	0.0413 (8)	0.0146 (7)	0.0100 (7)	0.0199 (7)
C13	0.0441 (8)	0.0422 (8)	0.0390 (8)	0.0079 (6)	0.0039 (6)	0.0094 (6)
C14	0.0466 (9)	0.0431 (8)	0.0316 (7)	0.0126 (7)	0.0018 (6)	0.0050 (6)
C15	0.0493 (9)	0.0521 (9)	0.0389 (8)	0.0147 (7)	0.0011 (7)	0.0042 (7)
C16	0.0635 (11)	0.0561 (10)	0.0374 (8)	0.0255 (8)	−0.0058 (7)	0.0032 (7)
C17	0.0792 (13)	0.0498 (9)	0.0364 (8)	0.0240 (9)	−0.0012 (8)	0.0114 (7)
C18	0.0666 (11)	0.0433 (8)	0.0389 (8)	0.0148 (8)	0.0045 (7)	0.0112 (7)
C19	0.0494 (9)	0.0458 (8)	0.0369 (8)	0.0111 (7)	0.0004 (6)	0.0102 (7)
C20	0.0765 (14)	0.0919 (15)	0.0607 (12)	0.0335 (12)	−0.0152 (10)	0.0153 (11)
C21	0.0856 (14)	0.0608 (11)	0.0568 (11)	0.0146 (10)	0.0119 (10)	0.0272 (9)

O1—C19	1.3607 (19)	C9—C10	1.378 (2)
O1—H1B	0.94 (2)	C9—H9A	0.9300
O2—C21	1.207 (2)	C10—C12	1.503 (2)
N1—C5	1.3324 (19)	C11—H11A	0.9700
N1—C1	1.346 (2)	C11—H11B	0.9700
N2—C6	1.332 (2)	C12—H12A	0.9700
N2—C10	1.333 (2)	C12—H12B	0.9700
N3—C12	1.4640 (18)	C13—C14	1.505 (2)
N3—C13	1.4704 (19)	C13—H13A	0.9700
N3—C11	1.4719 (18)	C13—H13B	0.9700
C1—C2	1.367 (3)	C14—C15	1.384 (2)
C1—H1A	0.9300	C14—C19	1.401 (2)
C2—C3	1.363 (3)	C15—C16	1.396 (2)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.372 (3)	C16—C17	1.372 (3)
C3—H3A	0.9300	C16—C20	1.512 (2)
C4—C5	1.382 (2)	C17—C18	1.394 (2)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C11	1.501 (2)	C18—C19	1.397 (2)
C6—C7	1.364 (3)	C18—C21	1.469 (3)
C6—H6A	0.9300	C20—H20A	0.9600
C7—C8	1.365 (3)	C20—H20B	0.9600
C7—H7A	0.9300	C20—H20C	0.9600
C8—C9	1.376 (3)	C21—H21A	0.9300
C8—H8A	0.9300
C19—O1—H1B	106.1 (14)	H11A—C11—H11B	107.9
C5—N1—C1	117.31 (15)	N3—C12—C10	112.76 (11)
C6—N2—C10	117.32 (15)	N3—C12—H12A	109.0
C12—N3—C13	110.23 (11)	C10—C12—H12A	109.0
C12—N3—C11	111.29 (11)	N3—C12—H12B	109.0
C13—N3—C11	110.37 (11)	C10—C12—H12B	109.0
N1—C1—C2	123.62 (17)	H12A—C12—H12B	107.8
N1—C1—H1A	118.2	N3—C13—C14	112.35 (12)
C2—C1—H1A	118.2	N3—C13—H13A	109.1
C3—C2—C1	118.53 (17)	C14—C13—H13A	109.1
C3—C2—H2A	120.7	N3—C13—H13B	109.1
C1—C2—H2A	120.7	C14—C13—H13B	109.1
C2—C3—C4	119.06 (18)	H13A—C13—H13B	107.9
C2—C3—H3A	120.5	C15—C14—C19	118.35 (14)
C4—C3—H3A	120.5	C15—C14—C13	121.45 (14)
C3—C4—C5	119.49 (17)	C19—C14—C13	120.11 (13)
C3—C4—H4A	120.3	C14—C15—C16	122.85 (16)
C5—C4—H4A	120.3	C14—C15—H15A	118.6
N1—C5—C4	121.98 (14)	C16—C15—H15A	118.6
N1—C5—C11	117.07 (13)	C17—C16—C15	117.36 (15)
C4—C5—C11	120.95 (13)	C17—C16—C20	122.75 (17)
N2—C6—C7	124.44 (17)	C15—C16—C20	119.87 (18)
N2—C6—H6A	117.8	C16—C17—C18	122.13 (15)
C7—C6—H6A	117.8	C16—C17—H17A	118.9
C6—C7—C8	117.75 (16)	C18—C17—H17A	118.9
C6—C7—H7A	121.1	C17—C18—C19	119.25 (16)
C8—C7—H7A	121.1	C17—C18—C21	120.01 (15)
C7—C8—C9	119.36 (17)	C19—C18—C21	120.66 (16)
C7—C8—H8A	120.3	O1—C19—C18	118.99 (15)
C9—C8—H8A	120.3	O1—C19—C14	121.01 (13)
C8—C9—C10	119.11 (17)	C18—C19—C14	119.96 (15)
C8—C9—H9A	120.4	C16—C20—H20A	109.5
C10—C9—H9A	120.4	C16—C20—H20B	109.5
N2—C10—C9	122.01 (14)	H20A—C20—H20B	109.5
N2—C10—C12	116.25 (13)	C16—C20—H20C	109.5
C9—C10—C12	121.74 (14)	H20A—C20—H20C	109.5
N3—C11—C5	112.23 (12)	H20B—C20—H20C	109.5
N3—C11—H11A	109.2	O2—C21—C18	124.0 (2)
C5—C11—H11A	109.2	O2—C21—H21A	118.0
N3—C11—H11B	109.2	C18—C21—H21A	118.0
C5—C11—H11B	109.2

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N2	0.94 (3)	2.53 (3)	3.219 (2)	130 (2)
O1—H1B···N3	0.94 (3)	1.95 (3)	2.790 (2)	148 (2)
C3—H3A···N2i	0.93	2.59	3.390 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N2	0.94 (3)	2.53 (3)	3.219 (2)	130 (2)
O1—H1B⋯N3	0.94 (3)	1.95 (3)	2.790 (2)	148 (2)
C3—H3A⋯N2i	0.93	2.59	3.390 (3)	145

Symmetry code: (i) .