3,5-Dimeth-oxy-N,N-bis-(2-pyridylmeth-yl)aniline.

In the title mol-ecule, C(20)H(21)N(3)O(2), the benzene ring forms dihedral angles of 80.8 (1) and 83.5 (1)° with the two terminal pyridine rings. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link the mol-ecules into chains propagating in [001].

Related literature

For general background to organic ligand-based crystal mater­ials, see: Desiraju (2007 ▶); Moulton & Zaworotko (2001 ▶). For related structures, see: Frisch & Cahil (2008 ▶); Shattock et al. (2008 ▶); Shirman et al. (2008 ▶).

Experimental

Crystal data

C20H21N3O2

M = 335.40

Monoclinic,

a = 15.630 (3) Å

b = 5.9562 (12) Å

c = 20.088 (4) Å

β = 111.55 (3)°

V = 1739.3 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 113 K

0.27 × 0.25 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.978, T max = 0.983

14749 measured reflections

4106 independent reflections

3258 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.113

S = 1.10

4106 reflections

228 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048685/cv2657sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809048685/cv2657Isup2.hkl

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

C20H21N3O2	F(000) = 712
Mr = 335.40	Dx = 1.281 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4823 reflections
a = 15.630 (3) Å	θ = 2.2–27.9°
b = 5.9562 (12) Å	µ = 0.08 mm−1
c = 20.088 (4) Å	T = 113 K
β = 111.55 (3)°	Block, colourless
V = 1739.3 (6) Å3	0.27 × 0.25 × 0.20 mm
Z = 4

Rigaku Saturn CCD area-detector diffractometer	4106 independent reflections
Radiation source: rotating anode	3258 reflections with I > 2σ(I)
confocal	Rint = 0.038
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −20→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −7→7
Tmin = 0.978, Tmax = 0.983	l = −26→26
14749 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0655P)2] where P = (Fo2 + 2Fc2)/3
4106 reflections	(Δ/σ)max = 0.001
228 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.21 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
O1	0.46394 (5)	0.69311 (15)	0.32987 (5)	0.0298 (2)
O2	0.67567 (5)	0.25014 (13)	0.51460 (4)	0.0262 (2)
N1	0.79174 (6)	0.85369 (16)	0.41961 (5)	0.0225 (2)
N2	0.76094 (6)	1.11713 (16)	0.24609 (5)	0.0232 (2)
N3	0.98074 (6)	0.69084 (17)	0.58297 (5)	0.0270 (2)
C1	0.56528 (7)	0.47409 (19)	0.42047 (6)	0.0225 (2)
H1	0.5142	0.3882	0.4208	0.027*
C2	0.55351 (7)	0.65475 (19)	0.37374 (6)	0.0223 (2)
C3	0.62677 (7)	0.78159 (19)	0.37172 (6)	0.0215 (2)
H3	0.6168	0.9019	0.3387	0.026*
C4	0.71674 (7)	0.72922 (18)	0.41968 (6)	0.0195 (2)
C5	0.72901 (7)	0.55021 (18)	0.46686 (6)	0.0203 (2)
H5	0.7889	0.5140	0.4995	0.024*
C6	0.65369 (7)	0.42403 (18)	0.46634 (6)	0.0204 (2)
C7	0.60170 (8)	0.1182 (2)	0.51853 (7)	0.0298 (3)
H7A	0.5602	0.2138	0.5326	0.045*
H7B	0.6261	−0.0012	0.5540	0.045*
H7C	0.5679	0.0513	0.4716	0.045*
C8	0.44478 (8)	0.8805 (2)	0.28219 (7)	0.0334 (3)
H8A	0.4656	1.0189	0.3098	0.050*
H8B	0.3784	0.8893	0.2550	0.050*
H8C	0.4772	0.8618	0.2490	0.050*
C9	0.78119 (8)	1.03228 (18)	0.36833 (6)	0.0226 (2)
H9A	0.8346	1.1346	0.3873	0.027*
H9B	0.7254	1.1196	0.3637	0.027*
C10	0.77348 (7)	0.95312 (18)	0.29448 (6)	0.0196 (2)
C11	0.78065 (8)	0.72861 (19)	0.27911 (6)	0.0260 (3)
H11	0.7887	0.6166	0.3145	0.031*
C12	0.77589 (9)	0.6707 (2)	0.21078 (7)	0.0317 (3)
H12	0.7814	0.5183	0.1990	0.038*
C13	0.76299 (9)	0.8373 (2)	0.16036 (6)	0.0308 (3)
H13	0.7597	0.8028	0.1133	0.037*
C14	0.75496 (8)	1.0555 (2)	0.18028 (6)	0.0271 (3)
H14	0.7445	1.1696	0.1451	0.033*
C15	0.88451 (7)	0.7731 (2)	0.45984 (6)	0.0234 (3)
H15A	0.9269	0.8364	0.4383	0.028*
H15B	0.8854	0.6077	0.4553	0.028*
C16	0.91979 (7)	0.83373 (19)	0.53877 (6)	0.0210 (2)
C17	1.01752 (8)	0.7486 (2)	0.65253 (7)	0.0306 (3)
H17	1.0602	0.6481	0.6846	0.037*
C18	0.99727 (8)	0.9438 (2)	0.68009 (7)	0.0317 (3)
H18	1.0265	0.9791	0.7294	0.038*
C19	0.93321 (8)	1.0875 (2)	0.63410 (7)	0.0327 (3)
H19	0.9168	1.2229	0.6514	0.039*
C20	0.89329 (8)	1.0310 (2)	0.56236 (6)	0.0272 (3)
H20	0.8484	1.1260	0.5298	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0161 (4)	0.0381 (5)	0.0312 (5)	−0.0010 (3)	0.0040 (3)	0.0086 (4)
O2	0.0244 (4)	0.0261 (5)	0.0271 (4)	−0.0037 (3)	0.0083 (3)	0.0054 (3)
N1	0.0175 (5)	0.0297 (5)	0.0204 (5)	−0.0037 (4)	0.0069 (4)	0.0031 (4)
N2	0.0220 (5)	0.0220 (5)	0.0235 (5)	−0.0002 (4)	0.0058 (4)	0.0019 (4)
N3	0.0217 (5)	0.0299 (6)	0.0281 (5)	0.0012 (4)	0.0075 (4)	0.0028 (4)
C1	0.0184 (5)	0.0268 (6)	0.0234 (6)	−0.0056 (4)	0.0090 (4)	−0.0015 (5)
C2	0.0177 (5)	0.0289 (6)	0.0200 (5)	0.0005 (4)	0.0066 (4)	−0.0014 (5)
C3	0.0208 (5)	0.0243 (6)	0.0199 (5)	−0.0005 (4)	0.0082 (4)	0.0012 (4)
C4	0.0188 (5)	0.0233 (6)	0.0182 (5)	−0.0030 (4)	0.0089 (4)	−0.0046 (4)
C5	0.0166 (5)	0.0248 (6)	0.0190 (5)	−0.0006 (4)	0.0058 (4)	−0.0023 (4)
C6	0.0242 (6)	0.0210 (6)	0.0173 (5)	−0.0013 (4)	0.0093 (4)	−0.0018 (4)
C7	0.0315 (7)	0.0280 (6)	0.0317 (7)	−0.0062 (5)	0.0137 (5)	0.0036 (5)
C8	0.0237 (6)	0.0366 (7)	0.0342 (7)	0.0031 (5)	0.0040 (5)	0.0092 (6)
C9	0.0227 (5)	0.0220 (6)	0.0248 (6)	−0.0050 (4)	0.0109 (5)	−0.0017 (5)
C10	0.0147 (5)	0.0217 (6)	0.0220 (5)	−0.0023 (4)	0.0062 (4)	0.0003 (4)
C11	0.0338 (6)	0.0201 (6)	0.0268 (6)	−0.0021 (5)	0.0142 (5)	0.0030 (5)
C12	0.0460 (7)	0.0209 (6)	0.0321 (7)	−0.0032 (5)	0.0190 (6)	−0.0039 (5)
C13	0.0400 (7)	0.0305 (7)	0.0235 (6)	−0.0057 (5)	0.0135 (5)	−0.0032 (5)
C14	0.0300 (6)	0.0262 (6)	0.0218 (6)	−0.0036 (5)	0.0056 (5)	0.0039 (5)
C15	0.0162 (5)	0.0305 (6)	0.0247 (6)	−0.0033 (4)	0.0091 (4)	−0.0020 (5)
C16	0.0143 (5)	0.0239 (6)	0.0252 (6)	−0.0033 (4)	0.0076 (4)	0.0006 (5)
C17	0.0214 (6)	0.0402 (7)	0.0278 (6)	0.0024 (5)	0.0062 (5)	0.0070 (6)
C18	0.0232 (6)	0.0474 (8)	0.0228 (6)	−0.0051 (5)	0.0065 (5)	−0.0037 (6)
C19	0.0307 (7)	0.0334 (7)	0.0347 (7)	−0.0018 (5)	0.0129 (6)	−0.0090 (6)
C20	0.0217 (6)	0.0277 (6)	0.0297 (6)	0.0024 (5)	0.0063 (5)	0.0003 (5)

O1—C2	1.3719 (14)	C8—H8B	0.9800
O1—C8	1.4290 (15)	C8—H8C	0.9800
O2—C6	1.3733 (13)	C9—C10	1.5185 (15)
O2—C7	1.4237 (14)	C9—H9A	0.9900
N1—C4	1.3872 (14)	C9—H9B	0.9900
N1—C9	1.4475 (14)	C10—C11	1.3862 (16)
N1—C15	1.4577 (14)	C11—C12	1.3905 (17)
N2—C10	1.3408 (14)	C11—H11	0.9500
N2—C14	1.3417 (15)	C12—C13	1.3788 (17)
N3—C16	1.3411 (15)	C12—H12	0.9500
N3—C17	1.3458 (16)	C13—C14	1.3794 (18)
C1—C6	1.3827 (16)	C13—H13	0.9500
C1—C2	1.3949 (16)	C14—H14	0.9500
C1—H1	0.9500	C15—C16	1.5185 (16)
C2—C3	1.3847 (15)	C15—H15A	0.9900
C3—C4	1.4169 (16)	C15—H15B	0.9900
C3—H3	0.9500	C16—C20	1.3859 (16)
C4—C5	1.3923 (15)	C17—C18	1.3738 (18)
C5—C6	1.3935 (15)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.3816 (18)
C7—H7A	0.9800	C18—H18	0.9500
C7—H7B	0.9800	C19—C20	1.3852 (17)
C7—H7C	0.9800	C19—H19	0.9500
C8—H8A	0.9800	C20—H20	0.9500
C2—O1—C8	118.28 (9)	N1—C9—H9B	108.6
C6—O2—C7	117.23 (9)	C10—C9—H9B	108.6
C4—N1—C9	121.20 (9)	H9A—C9—H9B	107.6
C4—N1—C15	119.49 (9)	N2—C10—C11	122.92 (10)
C9—N1—C15	117.81 (9)	N2—C10—C9	114.84 (9)
C10—N2—C14	116.99 (10)	C11—C10—C9	122.23 (10)
C16—N3—C17	116.98 (11)	C10—C11—C12	118.68 (11)
C6—C1—C2	117.86 (10)	C10—C11—H11	120.7
C6—C1—H1	121.1	C12—C11—H11	120.7
C2—C1—H1	121.1	C13—C12—C11	119.13 (12)
O1—C2—C3	123.36 (10)	C13—C12—H12	120.4
O1—C2—C1	114.32 (10)	C11—C12—H12	120.4
C3—C2—C1	122.31 (10)	C12—C13—C14	118.00 (11)
C2—C3—C4	119.01 (10)	C12—C13—H13	121.0
C2—C3—H3	120.5	C14—C13—H13	121.0
C4—C3—H3	120.5	N2—C14—C13	124.25 (11)
N1—C4—C5	120.32 (10)	N2—C14—H14	117.9
N1—C4—C3	120.64 (10)	C13—C14—H14	117.9
C5—C4—C3	119.04 (10)	N1—C15—C16	113.97 (9)
C4—C5—C6	120.21 (10)	N1—C15—H15A	108.8
C4—C5—H5	119.9	C16—C15—H15A	108.8
C6—C5—H5	119.9	N1—C15—H15B	108.8
O2—C6—C1	124.25 (10)	C16—C15—H15B	108.8
O2—C6—C5	114.19 (9)	H15A—C15—H15B	107.7
C1—C6—C5	121.56 (10)	N3—C16—C20	122.72 (11)
O2—C7—H7A	109.5	N3—C16—C15	115.94 (10)
O2—C7—H7B	109.5	C20—C16—C15	121.27 (10)
H7A—C7—H7B	109.5	N3—C17—C18	124.13 (11)
O2—C7—H7C	109.5	N3—C17—H17	117.9
H7A—C7—H7C	109.5	C18—C17—H17	117.9
H7B—C7—H7C	109.5	C17—C18—C19	118.20 (12)
O1—C8—H8A	109.5	C17—C18—H18	120.9
O1—C8—H8B	109.5	C19—C18—H18	120.9
H8A—C8—H8B	109.5	C18—C19—C20	118.94 (12)
O1—C8—H8C	109.5	C18—C19—H19	120.5
H8A—C8—H8C	109.5	C20—C19—H19	120.5
H8B—C8—H8C	109.5	C19—C20—C16	119.00 (11)
N1—C9—C10	114.49 (9)	C19—C20—H20	120.5
N1—C9—H9A	108.6	C16—C20—H20	120.5
C10—C9—H9A	108.6
C8—O1—C2—C3	−3.27 (16)	C14—N2—C10—C11	0.28 (16)
C8—O1—C2—C1	177.50 (10)	C14—N2—C10—C9	179.13 (9)
C6—C1—C2—O1	179.80 (10)	N1—C9—C10—N2	178.10 (9)
C6—C1—C2—C3	0.56 (17)	N1—C9—C10—C11	−3.04 (15)
O1—C2—C3—C4	179.59 (10)	N2—C10—C11—C12	0.90 (17)
C1—C2—C3—C4	−1.24 (17)	C9—C10—C11—C12	−177.88 (10)
C9—N1—C4—C5	176.48 (9)	C10—C11—C12—C13	−0.87 (18)
C15—N1—C4—C5	10.78 (15)	C11—C12—C13—C14	−0.28 (18)
C9—N1—C4—C3	−3.31 (16)	C10—N2—C14—C13	−1.55 (17)
C15—N1—C4—C3	−169.01 (10)	C12—C13—C14—N2	1.56 (19)
C2—C3—C4—N1	−179.48 (10)	C4—N1—C15—C16	−83.43 (13)
C2—C3—C4—C5	0.72 (16)	C9—N1—C15—C16	110.39 (11)
N1—C4—C5—C6	−179.36 (10)	C17—N3—C16—C20	−1.19 (16)
C3—C4—C5—C6	0.44 (16)	C17—N3—C16—C15	175.75 (9)
C7—O2—C6—C1	−1.89 (16)	N1—C15—C16—N3	150.93 (10)
C7—O2—C6—C5	178.13 (10)	N1—C15—C16—C20	−32.08 (14)
C2—C1—C6—O2	−179.33 (10)	C16—N3—C17—C18	−0.83 (18)
C2—C1—C6—C5	0.65 (16)	N3—C17—C18—C19	1.91 (19)
C4—C5—C6—O2	178.84 (9)	C17—C18—C19—C20	−0.95 (18)
C4—C5—C6—C1	−1.15 (17)	C18—C19—C20—C16	−0.90 (18)
C4—N1—C9—C10	−79.37 (13)	N3—C16—C20—C19	2.06 (17)
C15—N1—C9—C10	86.56 (12)	C15—C16—C20—C19	−174.73 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O2i	0.95	2.49	3.3050 (15)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O2i	0.95	2.49	3.3050 (15)	144

Symmetry code: (i) .