2-Phenyl-1,3-bis(2-pyridyl­methyl)­imidazolidine

Bjernemose, J.K.; McKenzie, C.J.; Mortensen, M.N.

doi:10.1107/S1600536803013394

2-Phenyl-1,3-bis(2-pyridylmethyl)imidazolidine

J. K. Bjernemose, C. J. McKenzie and M. N. Mortensen

In the title compound, C₂₁H₂₂N₄, all three substituents are found in equatorial positions. Intermolecular C—H

N and C—H

π interactions seem to be responsible for the packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013394/na6244sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013394/na6244Isup2.hkl Contains datablock I

CCDC reference: 217603

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R factor = 0.049
wR factor = 0.111
Data-to-parameter ratio = 17.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

Comment top

Subsequent to the publication of some coordination compounds with the ligand N-benzyl-N'-carboxymethyl-N,N'-bis(2-pyridylmethyl)-1,2-ethanediamine (Baffert et al., 2003) we have succeeded in crystallizing the ligand precursor 2-phenyl-1,3-bis(2-pyridylmethyl)imidazolidine, (I).

Fig. 1 shows the molecular structure of (I) with atom-numbering scheme. The five-membered ring is in the envelope conformation with the apex on C3 [ϕ₂ = 5.6 (2)°, total ring puckering amplitude Q₂ = 0.3974 (16) Å (Cremer & Pople, 1975)]. This has a pseudo-mirror that includes the phenyl ring through C3 and orthogonal to the C1—C2 bond. All three substituents are in equatorial positions and the pyridine rings are oriented in a syn fashion i.e. the two N atoms are both pointing in the same direction as the axial hydrogen on C2. The exact orientations of the central ring and substituents is summarized in table 1 by the dihedral angles formed by least-squares planes through the individual rings.

Extensive C—H···π interactions (closest contact 2.79 Å) exist between the aromatic rings. Short contacts include N1···H36ⁱ 3.48 Å, N2···H36ⁱ 3.07 Å, N11···H34ⁱⁱ 2.90 Å and N21···H2Bⁱⁱⁱ 2.76 Å [symmetry codes: (i) x + 1, y, z; (ii) x − 1/2, y − 1/2, 1/2 − z; (iii) −x, −y, −z]. The former two result in stacking along the a axis of the unit cell.

Experimental top

2-Phenyl-1,3-bis(2-pyridylmethyl)imidazolidine was prepared according to a literature method (Baffert et al., 2003). Colourless block-shaped single crystals suitable were grown by slow evaporation of a dichloromethane solution.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare, 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. View of (I) (50% probability displacement ellipsoids)

(I) top

Crystal data top

C₂₁H₂₂N₄	F(000) = 704
M_r = 330.43	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 415–419 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71069 Å
a = 6.003 (5) Å	Cell parameters from 22931 reflections
b = 15.175 (5) Å	θ = 2.7–26.2°
c = 19.237 (5) Å	µ = 0.08 mm⁻¹
β = 91.794 (5)°	T = 120 K
V = 1751.5 (16) Å³	Block, colourless
Z = 4	0.45 × 0.25 × 0.1 mm

Data collection top

Bruker SMART CCD diffractometer	2464 reflections with I > 2σ(I)
ω rotation scans	R_int = 0.083
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θ_max = 27.5°, θ_min = 1.7°
T_min = 0.883, T_max = 0.992	h = −7→7
20244 measured reflections	k = −19→19
4019 independent reflections	l = −24→24

Refinement top

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)] = 0.049	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0464P)² + 0.1083P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4019 reflections	Δρ_max = 0.24 e Å⁻³
227 parameters	Δρ_min = −0.2 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0053 (8)

Crystal data top

C₂₁H₂₂N₄	V = 1751.5 (16) Å³
M_r = 330.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.003 (5) Å	µ = 0.08 mm⁻¹
b = 15.175 (5) Å	T = 120 K
c = 19.237 (5) Å	0.45 × 0.25 × 0.1 mm
β = 91.794 (5)°

Data collection top

Bruker SMART CCD diffractometer	4019 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2464 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.992	R_int = 0.083
20244 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.02	Δρ_max = 0.24 e Å⁻³
4019 reflections	Δρ_min = −0.2 e Å⁻³
227 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.2844 (3)	0.04647 (11)	0.18605 (8)	0.0260 (4)
H1A	0.1993	−0.0068	0.1986	0.031*
H1B	0.4346	0.0434	0.2087	0.031*
C2	0.3002 (3)	0.05436 (11)	0.10745 (8)	0.0236 (4)
H2A	0.4575	0.0594	0.0939	0.028*
H2B	0.232	0.0026	0.0838	0.028*
C3	0.0262 (3)	0.15051 (10)	0.14702 (8)	0.0180 (4)
H3	−0.1054	0.1102	0.143	0.022*
C11	0.0466 (3)	0.11771 (11)	0.27076 (8)	0.0216 (4)
H11A	−0.0382	0.0617	0.2692	0.026*
H11B	−0.062	0.1665	0.2736	0.026*
C12	0.1960 (3)	0.11853 (10)	0.33514 (8)	0.0189 (4)
C13	0.4076 (3)	0.15388 (11)	0.33586 (9)	0.0231 (4)
H13	0.4666	0.1775	0.2946	0.028*
C14	0.5330 (3)	0.15462 (11)	0.39737 (9)	0.0285 (4)
H14	0.6796	0.1783	0.3989	0.034*
C15	0.4416 (3)	0.12039 (12)	0.45635 (9)	0.0306 (5)
H15	0.523	0.1204	0.4995	0.037*
C16	0.2294 (3)	0.08624 (12)	0.45123 (9)	0.0308 (5)
H16	0.167	0.0626	0.492	0.037*
C21	0.0582 (3)	0.13274 (11)	0.02272 (8)	0.0221 (4)
H21A	−0.0497	0.1821	0.02	0.026*
H21B	−0.0273	0.0771	0.0191	0.026*
C22	0.2104 (3)	0.13883 (10)	−0.03784 (8)	0.0196 (4)
C23	0.4226 (3)	0.17400 (11)	−0.03124 (9)	0.0236 (4)
H23	0.4807	0.1926	0.0129	0.028*
C24	0.5488 (3)	0.18162 (11)	−0.08975 (9)	0.0280 (4)
H24	0.6954	0.2051	−0.0864	0.034*
C25	0.4592 (3)	0.15483 (11)	−0.15283 (9)	0.0285 (4)
H25	0.5411	0.16	−0.1941	0.034*
C26	0.2481 (3)	0.12041 (12)	−0.15444 (9)	0.0325 (5)
H26	0.187	0.1017	−0.1981	0.039*
C31	−0.0492 (3)	0.24523 (11)	0.14910 (8)	0.0182 (4)
C32	0.1092 (3)	0.31028 (11)	0.16163 (8)	0.0229 (4)
H32	0.2595	0.2941	0.1719	0.027*
C33	0.0513 (3)	0.39829 (11)	0.15932 (9)	0.0262 (4)
H33	0.1611	0.4423	0.168	0.031*
C34	−0.1676 (3)	0.42206 (11)	0.14433 (8)	0.0276 (4)
H34	−0.2078	0.4826	0.1418	0.033*
C35	−0.3260 (3)	0.35831 (11)	0.13308 (9)	0.0284 (4)
H35	−0.4763	0.3748	0.1232	0.034*
C36	−0.2681 (3)	0.26934 (11)	0.13606 (8)	0.0237 (4)
H36	−0.3794	0.2254	0.1291	0.028*
N1	0.1676 (2)	0.12666 (8)	0.20699 (7)	0.0189 (3)
N2	0.1755 (2)	0.13554 (8)	0.08983 (7)	0.0191 (3)
N11	0.1054 (2)	0.08435 (9)	0.39190 (7)	0.0245 (4)
N21	0.1221 (3)	0.11135 (9)	−0.09878 (7)	0.0277 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0327 (11)	0.0233 (9)	0.0219 (9)	0.0075 (8)	0.0014 (8)	0.0004 (8)
C2	0.0272 (10)	0.0214 (9)	0.0224 (9)	0.0035 (8)	0.0029 (8)	0.0005 (7)
C3	0.0197 (9)	0.0185 (9)	0.0156 (8)	−0.0028 (7)	0.0003 (7)	−0.0005 (7)
C11	0.0222 (10)	0.0225 (9)	0.0200 (9)	−0.0033 (8)	0.0016 (7)	0.0001 (7)
C12	0.0223 (9)	0.0160 (8)	0.0185 (9)	0.0019 (7)	0.0022 (7)	−0.0014 (7)
C13	0.0263 (10)	0.0217 (9)	0.0215 (9)	0.0014 (8)	0.0018 (8)	−0.0011 (7)
C14	0.0275 (11)	0.0262 (10)	0.0316 (11)	0.0035 (8)	−0.0026 (9)	−0.0079 (8)
C15	0.0362 (12)	0.0333 (11)	0.0216 (10)	0.0052 (9)	−0.0071 (9)	−0.0028 (8)
C16	0.0425 (12)	0.0320 (10)	0.0179 (9)	−0.0015 (9)	0.0002 (8)	0.0025 (8)
C21	0.0235 (10)	0.0241 (9)	0.0185 (9)	−0.0012 (8)	−0.0016 (7)	−0.0010 (7)
C22	0.0249 (10)	0.0158 (9)	0.0181 (9)	0.0022 (7)	0.0000 (7)	0.0008 (7)
C23	0.0256 (10)	0.0265 (10)	0.0186 (9)	−0.0008 (8)	−0.0018 (8)	0.0016 (7)
C24	0.0257 (10)	0.0281 (10)	0.0302 (10)	0.0006 (8)	0.0022 (8)	0.0090 (8)
C25	0.0362 (12)	0.0264 (10)	0.0235 (10)	0.0030 (9)	0.0099 (9)	0.0038 (8)
C26	0.0450 (13)	0.0335 (11)	0.0192 (10)	−0.0034 (10)	0.0038 (9)	−0.0044 (8)
C31	0.0227 (10)	0.0215 (9)	0.0106 (8)	−0.0016 (7)	0.0027 (7)	−0.0010 (7)
C32	0.0255 (10)	0.0234 (9)	0.0199 (9)	−0.0007 (8)	0.0015 (7)	0.0001 (7)
C33	0.0342 (11)	0.0209 (9)	0.0237 (10)	−0.0058 (8)	0.0046 (8)	−0.0028 (7)
C34	0.0375 (12)	0.0208 (9)	0.0253 (10)	0.0061 (9)	0.0130 (9)	0.0014 (8)
C35	0.0248 (10)	0.0305 (11)	0.0304 (10)	0.0070 (9)	0.0085 (8)	0.0076 (8)
C36	0.0227 (10)	0.0230 (9)	0.0255 (10)	−0.0029 (8)	0.0025 (8)	0.0030 (8)
N1	0.0223 (8)	0.0187 (7)	0.0157 (7)	0.0023 (6)	0.0011 (6)	0.0005 (6)
N2	0.0221 (8)	0.0194 (7)	0.0157 (7)	0.0025 (6)	0.0004 (6)	−0.0002 (6)
N11	0.0306 (9)	0.0249 (8)	0.0182 (8)	−0.0011 (7)	0.0013 (7)	0.0003 (6)
N21	0.0340 (9)	0.0296 (8)	0.0196 (8)	−0.0043 (7)	0.0018 (7)	−0.0044 (6)

Geometric parameters (Å, º) top

C1—N1	1.467 (2)	C21—N2	1.452 (2)
C1—C2	1.523 (2)	C21—C22	1.506 (2)
C1—H1A	0.99	C21—H21A	0.99
C1—H1B	0.99	C21—H21B	0.99
C2—N2	1.476 (2)	C22—N21	1.338 (2)
C2—H2A	0.99	C22—C23	1.383 (3)
C2—H2B	0.99	C23—C24	1.381 (2)
C3—N1	1.456 (2)	C23—H23	0.95
C3—N2	1.459 (2)	C24—C25	1.373 (2)
C3—C31	1.508 (2)	C24—H24	0.95
C3—H3	1	C25—C26	1.370 (3)
C11—N1	1.451 (2)	C25—H25	0.95
C11—C12	1.506 (2)	C26—N21	1.337 (2)
C11—H11A	0.99	C26—H26	0.95
C11—H11B	0.99	C31—C36	1.380 (3)
C12—N11	1.340 (2)	C31—C32	1.387 (2)
C12—C13	1.379 (3)	C32—C33	1.380 (2)
C13—C14	1.382 (2)	C32—H32	0.95
C13—H13	0.95	C33—C34	1.384 (3)
C14—C15	1.377 (3)	C33—H33	0.95
C14—H14	0.95	C34—C35	1.369 (2)
C15—C16	1.376 (3)	C34—H34	0.95
C15—H15	0.95	C35—C36	1.395 (2)
C16—N11	1.343 (2)	C35—H35	0.95
C16—H16	0.95	C36—H36	0.95

N1—C1—C2	104.64 (13)	C22—C21—H21B	108.9
N1—C1—H1A	110.8	H21A—C21—H21B	107.7
C2—C1—H1A	110.8	N21—C22—C23	122.62 (15)
N1—C1—H1B	110.8	N21—C22—C21	115.19 (15)
C2—C1—H1B	110.8	C23—C22—C21	122.14 (15)
H1A—C1—H1B	108.9	C24—C23—C22	118.97 (16)
N2—C2—C1	104.28 (13)	C24—C23—H23	120.5
N2—C2—H2A	110.9	C22—C23—H23	120.5
C1—C2—H2A	110.9	C25—C24—C23	119.08 (17)
N2—C2—H2B	110.9	C25—C24—H24	120.5
C1—C2—H2B	110.9	C23—C24—H24	120.5
H2A—C2—H2B	108.9	C26—C25—C24	117.97 (17)
N1—C3—N2	101.65 (13)	C26—C25—H25	121
N1—C3—C31	112.57 (13)	C24—C25—H25	121
N2—C3—C31	111.13 (12)	N21—C26—C25	124.54 (17)
N1—C3—H3	110.4	N21—C26—H26	117.7
N2—C3—H3	110.4	C25—C26—H26	117.7
C31—C3—H3	110.4	C36—C31—C32	119.16 (16)
N1—C11—C12	113.17 (14)	C36—C31—C3	122.21 (15)
N1—C11—H11A	108.9	C32—C31—C3	118.57 (15)
C12—C11—H11A	108.9	C33—C32—C31	120.81 (17)
N1—C11—H11B	108.9	C33—C32—H32	119.6
C12—C11—H11B	108.9	C31—C32—H32	119.6
H11A—C11—H11B	107.8	C32—C33—C34	119.70 (16)
N11—C12—C13	122.69 (16)	C32—C33—H33	120.2
N11—C12—C11	114.87 (15)	C34—C33—H33	120.2
C13—C12—C11	122.43 (15)	C35—C34—C33	119.93 (17)
C12—C13—C14	119.26 (17)	C35—C34—H34	120
C12—C13—H13	120.4	C33—C34—H34	120
C14—C13—H13	120.4	C34—C35—C36	120.44 (17)
C15—C14—C13	118.78 (18)	C34—C35—H35	119.8
C15—C14—H14	120.6	C36—C35—H35	119.8
C13—C14—H14	120.6	C31—C36—C35	119.92 (16)
C16—C15—C14	118.37 (17)	C31—C36—H36	120
C16—C15—H15	120.8	C35—C36—H36	120
C14—C15—H15	120.8	C11—N1—C3	113.45 (13)
N11—C16—C15	123.79 (17)	C11—N1—C1	114.23 (13)
N11—C16—H16	118.1	C3—N1—C1	105.09 (12)
C15—C16—H16	118.1	C21—N2—C3	112.52 (13)
N2—C21—C22	113.40 (14)	C21—N2—C2	114.10 (13)
N2—C21—H21A	108.9	C3—N2—C2	106.04 (12)
C22—C21—H21A	108.9	C12—N11—C16	117.11 (15)
N2—C21—H21B	108.9	C26—N21—C22	116.82 (16)

N1—C1—C2—N2	−4.15 (18)	C3—C31—C36—C35	−174.81 (15)
N1—C11—C12—N11	−160.54 (13)	C34—C35—C36—C31	−1.3 (3)
N1—C11—C12—C13	21.1 (2)	C12—C11—N1—C3	−163.80 (13)
N11—C12—C13—C14	−0.1 (2)	C12—C11—N1—C1	75.77 (17)
C11—C12—C13—C14	178.16 (15)	N2—C3—N1—C11	−167.80 (12)
C12—C13—C14—C15	−0.4 (2)	C31—C3—N1—C11	73.23 (16)
C13—C14—C15—C16	0.5 (3)	N2—C3—N1—C1	−42.33 (15)
C14—C15—C16—N11	−0.1 (3)	C31—C3—N1—C1	−161.30 (13)
N2—C21—C22—N21	161.40 (14)	C2—C1—N1—C11	153.77 (14)
N2—C21—C22—C23	−21.3 (2)	C2—C1—N1—C3	28.79 (17)
N21—C22—C23—C24	0.3 (2)	C22—C21—N2—C3	166.43 (13)
C21—C22—C23—C24	−176.72 (15)	C22—C21—N2—C2	−72.70 (17)
C22—C23—C24—C25	0.6 (2)	N1—C3—N2—C21	165.09 (12)
C23—C24—C25—C26	−0.9 (3)	C31—C3—N2—C21	−74.92 (16)
C24—C25—C26—N21	0.3 (3)	N1—C3—N2—C2	39.70 (15)
N1—C3—C31—C36	−133.08 (16)	C31—C3—N2—C2	159.69 (13)
N2—C3—C31—C36	113.65 (17)	C1—C2—N2—C21	−146.35 (14)
N1—C3—C31—C32	49.73 (19)	C1—C2—N2—C3	−21.94 (17)
N2—C3—C31—C32	−63.54 (18)	C13—C12—N11—C16	0.5 (2)
C36—C31—C32—C33	−1.8 (2)	C11—C12—N11—C16	−177.85 (14)
C3—C31—C32—C33	175.52 (14)	C15—C16—N11—C12	−0.5 (3)
C31—C32—C33—C34	0.0 (2)	C25—C26—N21—C22	0.6 (3)
C32—C33—C34—C35	1.1 (2)	C23—C22—N21—C26	−0.9 (2)
C33—C34—C35—C36	−0.5 (3)	C21—C22—N21—C26	176.36 (15)
C32—C31—C36—C35	2.4 (2)

Experimental details

Crystal data
Chemical formula	C₂₁H₂₂N₄
M_r	330.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	6.003 (5), 15.175 (5), 19.237 (5)
β (°)	91.794 (5)
V (Å³)	1751.5 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.25 × 0.1

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.883, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	20244, 4019, 2464
R_int	0.083
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.111, 1.02
No. of reflections	4019
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.2

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR97 (Altomare, 1999), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

C1—N1	1.467 (2)	C2—N2	1.476 (2)
C1—C2	1.523 (2)	C3—N1	1.456 (2)

N1—C1—C2	104.64 (13)	C3—N1—C1	105.09 (12)
N2—C2—C1	104.28 (13)	C3—N2—C2	106.04 (12)
N1—C3—N2	101.65 (13)

Dihedral angles formed by least-squares planes (°) top

	II	III	IV
I	21.97 (8)	73.97 (8)	70.71 (9)
II		84.34 (8)	71.65 (9)
III			85.44 (9)

Least-squares planes: I N11/C12–C16, II N21/C22–C26, III C31–C36 and IV N1/C1/C2/N2/C3

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2-Phenyl-1,3-bis(2-pyridyl­methyl)­imidazolidine

Supporting information

Key indicators

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2-Phenyl-1,3-bis(2-pyridylmethyl)imidazolidine