2,6-Bis[1-(2,6-dimethyl­phenyl­imino)eth­yl]pyridine

In the mol­ecule of the title compound, C₂₅H₂₇N₃, the two 2,6-dimethyl-substituted phenyl rings are connected to the pyridine ring via the C=N imine bonds. Although the compound includes three N atoms, there are no obvious hydrogen-bond or π–π inter­actions in the crystal structure.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.053
• wR factor = 0.180
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.861     0.994
            Tmin(prime) and Tmax expected:      0.956     0.964
            RR(prime) =      0.873
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.87
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.65 mm
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C7
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety         C9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C16
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C17
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C25

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  10 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: TEXSAN (Molecular Structure Corporation, 1998); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.

2,6-Bis[1-(2,6-dimethylphenylimino)ethyl]pyridine

Crystal data

C25H27N3	F(000) = 792
Mr = 369.51	Dx = 1.126 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4978 reflections
a = 10.340 (6) Å	θ = 3.1–27.5°
b = 14.433 (5) Å	µ = 0.07 mm^−1
c = 15.185 (7) Å	T = 296 K
β = 105.92 (2)°	Block, yellow
V = 2179.2 (17) Å^3	0.65 × 0.58 × 0.55 mm
Z = 4

Data collection

Rigaku Weissenberg IP diffractometer	4978 independent reflections
Radiation source: fine-focus sealed tube	3655 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (TEXSAN; Molecular Structure Corporation, 1998)	h = −13→13
Tmin = 0.861, Tmax = 0.994	k = −18→18
20802 measured reflections	l = −19→19

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.180	w = 1/[σ^2(Fo^2) + (0.0998P)^2 + 0.19P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
4978 reflections	Δρmax = 0.25 e Å^−3
254 parameters	Δρmin = −0.20 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (3)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.24509 (11)	0.76484 (7)	−0.00215 (7)	0.0454 (3)
N2	0.17681 (13)	0.56283 (9)	−0.13889 (9)	0.0564 (3)
N3	0.22111 (13)	0.98389 (9)	0.09485 (9)	0.0569 (3)
C1	0.17268 (14)	0.70416 (9)	−0.06226 (9)	0.0449 (3)
C2	0.03544 (15)	0.71403 (10)	−0.10135 (10)	0.0523 (4)
H2	−0.0128	0.6695	−0.1414	0.063*
C3	−0.02789 (15)	0.79125 (11)	−0.07961 (11)	0.0562 (4)
H3	−0.1195	0.8002	−0.1058	0.067*
C4	0.04590 (15)	0.85506 (10)	−0.01857 (10)	0.0523 (4)
H4	0.0051	0.9077	−0.0031	0.063*
C5	0.18227 (14)	0.83920 (9)	0.01941 (9)	0.0451 (3)
C6	0.24624 (15)	0.62204 (9)	−0.08462 (9)	0.0481 (3)
C7	0.39431 (16)	0.61589 (12)	−0.03964 (14)	0.0717 (5)
H7A	0.4293	0.5603	−0.0592	0.108*
H7B	0.4099	0.6146	0.0257	0.108*
H7C	0.4385	0.6688	−0.0565	0.108*
C8	0.26610 (15)	0.90273 (10)	0.08977 (9)	0.0480 (3)
C9	0.39338 (18)	0.86447 (13)	0.14983 (13)	0.0717 (5)
H9A	0.4384	0.9113	0.1920	0.108*
H9B	0.4504	0.8449	0.1130	0.108*
H9C	0.3735	0.8124	0.1833	0.108*
C10	0.23472 (15)	0.47941 (10)	−0.16091 (10)	0.0536 (4)
C11	0.23720 (19)	0.40144 (11)	−0.10691 (12)	0.0665 (4)
C12	0.2833 (2)	0.31838 (12)	−0.13485 (15)	0.0770 (5)
H12	0.2863	0.2655	−0.0994	0.092*
C13	0.3239 (2)	0.31325 (12)	−0.21301 (14)	0.0771 (6)
H13	0.3534	0.2572	−0.2308	0.093*
C14	0.3212 (2)	0.39062 (12)	−0.26485 (13)	0.0710 (5)
H14	0.3500	0.3868	−0.3177	0.085*
C15	0.27657 (17)	0.47510 (11)	−0.24066 (11)	0.0600 (4)
C16	0.1892 (3)	0.40681 (17)	−0.02265 (17)	0.1053 (8)
H16A	0.1617	0.4691	−0.0148	0.158*
H16B	0.2607	0.3892	0.0297	0.158*
H16C	0.1143	0.3656	−0.0288	0.158*
C17	0.2744 (2)	0.55996 (15)	−0.29847 (14)	0.0842 (6)
H17A	0.3064	0.5443	−0.3502	0.126*
H17B	0.3313	0.6067	−0.2627	0.126*
H17C	0.1840	0.5830	−0.3194	0.126*
C18	0.28857 (16)	1.04697 (11)	0.16436 (10)	0.0568 (4)
C19	0.38258 (18)	1.10893 (12)	0.14852 (12)	0.0654 (4)
C20	0.4335 (2)	1.17611 (15)	0.21438 (15)	0.0863 (6)
H20	0.4966	1.2182	0.2052	0.104*
C21	0.3922 (3)	1.18164 (18)	0.29294 (16)	0.0995 (8)
H21	0.4272	1.2271	0.3363	0.119*
C22	0.3004 (3)	1.12070 (19)	0.30682 (15)	0.0951 (7)
H22	0.2729	1.1252	0.3601	0.114*
C23	0.2460 (2)	1.05173 (14)	0.24407 (12)	0.0731 (5)
C24	0.4276 (3)	1.10361 (17)	0.06300 (15)	0.0942 (7)
H24A	0.3823	1.0534	0.0256	0.141*
H24B	0.5230	1.0934	0.0788	0.141*
H24C	0.4065	1.1607	0.0297	0.141*
C25	0.1448 (3)	0.9837 (2)	0.25999 (17)	0.1046 (8)
H25A	0.1273	0.9967	0.3177	0.157*
H25B	0.1796	0.9220	0.2608	0.157*
H25C	0.0627	0.9890	0.2117	0.157*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0464 (6)	0.0421 (6)	0.0464 (6)	0.0059 (5)	0.0105 (5)	−0.0002 (5)
N2	0.0536 (7)	0.0513 (7)	0.0620 (7)	0.0036 (6)	0.0118 (6)	−0.0116 (6)
N3	0.0559 (7)	0.0510 (7)	0.0572 (7)	0.0131 (6)	0.0044 (6)	−0.0092 (6)
C1	0.0470 (7)	0.0427 (7)	0.0451 (6)	0.0047 (5)	0.0130 (6)	0.0037 (6)
C2	0.0476 (8)	0.0514 (7)	0.0544 (8)	0.0005 (6)	0.0081 (6)	−0.0017 (6)
C3	0.0422 (7)	0.0571 (8)	0.0658 (9)	0.0078 (6)	0.0087 (6)	0.0028 (7)
C4	0.0498 (8)	0.0469 (7)	0.0599 (8)	0.0115 (6)	0.0147 (7)	0.0022 (7)
C5	0.0486 (7)	0.0423 (6)	0.0439 (6)	0.0074 (6)	0.0119 (6)	0.0043 (5)
C6	0.0492 (8)	0.0433 (7)	0.0514 (7)	0.0038 (6)	0.0130 (6)	−0.0004 (6)
C7	0.0508 (9)	0.0588 (9)	0.0958 (13)	0.0113 (7)	0.0037 (9)	−0.0203 (9)
C8	0.0495 (8)	0.0468 (7)	0.0466 (7)	0.0096 (6)	0.0112 (6)	−0.0001 (6)
C9	0.0625 (10)	0.0634 (10)	0.0731 (10)	0.0172 (8)	−0.0085 (8)	−0.0117 (8)
C10	0.0500 (8)	0.0463 (7)	0.0600 (8)	0.0019 (6)	0.0074 (7)	−0.0106 (6)
C11	0.0735 (11)	0.0549 (9)	0.0679 (9)	−0.0086 (8)	0.0140 (8)	−0.0078 (8)
C12	0.0888 (13)	0.0467 (8)	0.0871 (12)	−0.0003 (8)	0.0100 (11)	0.0011 (9)
C13	0.0830 (13)	0.0541 (9)	0.0877 (13)	0.0143 (9)	0.0123 (10)	−0.0145 (9)
C14	0.0724 (11)	0.0676 (10)	0.0717 (10)	0.0159 (9)	0.0174 (9)	−0.0138 (9)
C15	0.0585 (9)	0.0575 (9)	0.0615 (9)	0.0096 (7)	0.0122 (7)	−0.0050 (7)
C16	0.152 (2)	0.0814 (14)	0.0972 (15)	−0.0188 (15)	0.0584 (16)	0.0025 (12)
C17	0.1001 (16)	0.0791 (12)	0.0781 (12)	0.0282 (11)	0.0326 (11)	0.0132 (10)
C18	0.0547 (8)	0.0528 (8)	0.0561 (8)	0.0175 (7)	0.0037 (7)	−0.0101 (7)
C19	0.0648 (10)	0.0584 (9)	0.0682 (10)	0.0095 (8)	0.0099 (8)	−0.0111 (8)
C20	0.0813 (13)	0.0719 (12)	0.0963 (14)	−0.0021 (10)	0.0085 (11)	−0.0234 (11)
C21	0.1068 (18)	0.0956 (16)	0.0840 (14)	0.0064 (14)	0.0057 (13)	−0.0463 (13)
C22	0.1046 (18)	0.1091 (17)	0.0713 (12)	0.0121 (15)	0.0235 (12)	−0.0331 (12)
C23	0.0726 (11)	0.0809 (12)	0.0631 (9)	0.0176 (10)	0.0141 (8)	−0.0143 (9)
C24	0.1117 (18)	0.0871 (14)	0.0906 (14)	−0.0153 (13)	0.0391 (13)	−0.0113 (12)
C25	0.1038 (18)	0.128 (2)	0.0931 (15)	−0.0073 (16)	0.0464 (14)	−0.0112 (15)

Geometric parameters (Å, º)

N1—C1	1.3364 (18)	C13—C14	1.362 (3)
N1—C5	1.3406 (17)	C13—H13	0.9300
N2—C6	1.2651 (19)	C14—C15	1.389 (2)
N2—C10	1.4247 (18)	C14—H14	0.9300
N3—C8	1.2705 (18)	C15—C17	1.503 (3)
N3—C18	1.423 (2)	C16—H16A	0.9600
C1—C2	1.387 (2)	C16—H16B	0.9600
C1—C6	1.4967 (19)	C16—H16C	0.9600
C2—C3	1.378 (2)	C17—H17A	0.9600
C2—H2	0.9300	C17—H17B	0.9600
C3—C4	1.379 (2)	C17—H17C	0.9600
C3—H3	0.9300	C18—C19	1.390 (3)
C4—C5	1.388 (2)	C18—C23	1.399 (2)
C4—H4	0.9300	C19—C20	1.389 (3)
C5—C8	1.492 (2)	C19—C24	1.497 (3)
C6—C7	1.498 (2)	C20—C21	1.375 (3)
C7—H7A	0.9600	C20—H20	0.9300
C7—H7B	0.9600	C21—C22	1.352 (4)
C7—H7C	0.9600	C21—H21	0.9300
C8—C9	1.487 (2)	C22—C23	1.386 (3)
C9—H9A	0.9600	C22—H22	0.9300
C9—H9B	0.9600	C23—C25	1.502 (3)
C9—H9C	0.9600	C24—H24A	0.9600
C10—C11	1.388 (2)	C24—H24B	0.9600
C10—C15	1.395 (2)	C24—H24C	0.9600
C11—C12	1.398 (3)	C25—H25A	0.9600
C11—C16	1.496 (3)	C25—H25B	0.9600
C12—C13	1.366 (3)	C25—H25C	0.9600
C12—H12	0.9300
C1—N1—C5	118.24 (12)	C13—C14—C15	121.51 (18)
C6—N2—C10	121.59 (13)	C13—C14—H14	119.2
C8—N3—C18	121.45 (13)	C15—C14—H14	119.2
N1—C1—C2	122.72 (13)	C14—C15—C10	118.28 (16)
N1—C1—C6	116.72 (12)	C14—C15—C17	120.91 (16)
C2—C1—C6	120.54 (13)	C10—C15—C17	120.80 (15)
C3—C2—C1	118.57 (14)	C11—C16—H16A	109.5
C3—C2—H2	120.7	C11—C16—H16B	109.5
C1—C2—H2	120.7	H16A—C16—H16B	109.5
C2—C3—C4	119.32 (14)	C11—C16—H16C	109.5
C2—C3—H3	120.3	H16A—C16—H16C	109.5
C4—C3—H3	120.3	H16B—C16—H16C	109.5
C3—C4—C5	118.73 (13)	C15—C17—H17A	109.5
C3—C4—H4	120.6	C15—C17—H17B	109.5
C5—C4—H4	120.6	H17A—C17—H17B	109.5
N1—C5—C4	122.38 (13)	C15—C17—H17C	109.5
N1—C5—C8	116.21 (12)	H17A—C17—H17C	109.5
C4—C5—C8	121.36 (12)	H17B—C17—H17C	109.5
N2—C6—C1	116.74 (13)	C19—C18—C23	121.31 (15)
N2—C6—C7	125.68 (13)	C19—C18—N3	120.47 (15)
C1—C6—C7	117.57 (12)	C23—C18—N3	117.81 (16)
C6—C7—H7A	109.5	C20—C19—C18	118.00 (18)
C6—C7—H7B	109.5	C20—C19—C24	120.9 (2)
H7A—C7—H7B	109.5	C18—C19—C24	121.07 (16)
C6—C7—H7C	109.5	C21—C20—C19	121.3 (2)
H7A—C7—H7C	109.5	C21—C20—H20	119.4
H7B—C7—H7C	109.5	C19—C20—H20	119.4
N3—C8—C9	125.63 (14)	C22—C21—C20	119.7 (2)
N3—C8—C5	117.37 (13)	C22—C21—H21	120.1
C9—C8—C5	116.97 (12)	C20—C21—H21	120.1
C8—C9—H9A	109.5	C21—C22—C23	122.0 (2)
C8—C9—H9B	109.5	C21—C22—H22	119.0
H9A—C9—H9B	109.5	C23—C22—H22	119.0
C8—C9—H9C	109.5	C22—C23—C18	117.7 (2)
H9A—C9—H9C	109.5	C22—C23—C25	121.9 (2)
H9B—C9—H9C	109.5	C18—C23—C25	120.40 (17)
C11—C10—C15	121.12 (14)	C19—C24—H24A	109.5
C11—C10—N2	119.16 (15)	C19—C24—H24B	109.5
C15—C10—N2	119.46 (14)	H24A—C24—H24B	109.5
C10—C11—C12	117.93 (17)	C19—C24—H24C	109.5
C10—C11—C16	120.43 (17)	H24A—C24—H24C	109.5
C12—C11—C16	121.63 (18)	H24B—C24—H24C	109.5
C13—C12—C11	121.47 (17)	C23—C25—H25A	109.5
C13—C12—H12	119.3	C23—C25—H25B	109.5
C11—C12—H12	119.3	H25A—C25—H25B	109.5
C14—C13—C12	119.69 (16)	C23—C25—H25C	109.5
C14—C13—H13	120.2	H25A—C25—H25C	109.5
C12—C13—H13	120.2	H25B—C25—H25C	109.5
C5—N1—C1—C2	−1.5 (2)	N2—C10—C11—C16	−4.6 (3)
C5—N1—C1—C6	180.00 (11)	C10—C11—C12—C13	−0.4 (3)
N1—C1—C2—C3	2.3 (2)	C16—C11—C12—C13	178.4 (2)
C6—C1—C2—C3	−179.28 (13)	C11—C12—C13—C14	0.7 (3)
C1—C2—C3—C4	−1.3 (2)	C12—C13—C14—C15	−0.7 (3)
C2—C3—C4—C5	−0.2 (2)	C13—C14—C15—C10	0.4 (3)
C1—N1—C5—C4	−0.2 (2)	C13—C14—C15—C17	179.90 (19)
C1—N1—C5—C8	177.46 (12)	C11—C10—C15—C14	−0.1 (2)
C3—C4—C5—N1	1.0 (2)	N2—C10—C15—C14	−174.22 (15)
C3—C4—C5—C8	−176.52 (13)	C11—C10—C15—C17	−179.63 (18)
C10—N2—C6—C1	−176.37 (13)	N2—C10—C15—C17	6.3 (2)
C10—N2—C6—C7	2.3 (2)	C8—N3—C18—C19	92.57 (19)
N1—C1—C6—N2	177.45 (12)	C8—N3—C18—C23	−94.71 (19)
C2—C1—C6—N2	−1.1 (2)	C23—C18—C19—C20	0.0 (2)
N1—C1—C6—C7	−1.30 (19)	N3—C18—C19—C20	172.47 (15)
C2—C1—C6—C7	−179.85 (15)	C23—C18—C19—C24	−179.89 (18)
C18—N3—C8—C9	−3.0 (3)	N3—C18—C19—C24	−7.4 (2)
C18—N3—C8—C5	175.01 (14)	C18—C19—C20—C21	−0.2 (3)
N1—C5—C8—N3	162.49 (13)	C24—C19—C20—C21	179.8 (2)
C4—C5—C8—N3	−19.8 (2)	C19—C20—C21—C22	0.0 (3)
N1—C5—C8—C9	−19.3 (2)	C20—C21—C22—C23	0.2 (4)
C4—C5—C8—C9	158.36 (15)	C21—C22—C23—C18	−0.3 (3)
C6—N2—C10—C11	89.4 (2)	C21—C22—C23—C25	179.6 (2)
C6—N2—C10—C15	−96.37 (18)	C19—C18—C23—C22	0.2 (3)
C15—C10—C11—C12	0.1 (3)	N3—C18—C23—C22	−172.43 (16)
N2—C10—C11—C12	174.25 (15)	C19—C18—C23—C25	−179.68 (18)
C15—C10—C11—C16	−178.68 (19)	N3—C18—C23—C25	7.7 (2)