N,N′-Di-2-pyridyl­methyl­enedi­amine

The title compound, C₁₁H₁₂N₄, was synthesized by the reaction of N,N-1,3-bis­(hydroxy­methyl)-5-fluoro­uracil with 2-amino­pyridine in ethanol in the absence of a catalyst. The pyridine rings are approximately perpendicular to one another and are linked in the crystal structue via intermolecular N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.039
• wR factor = 0.088
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.62 mm
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       6.02 su
PLAT420_ALERT_2_C D-H Without Acceptor       N2     -   H2N    ...          ?

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

N,N'-Di-2-pyridylmethylenediamine

Crystal data

C11H12N4	F(000) = 848
Mr = 200.25	Dx = 1.286 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 38 reflections
a = 17.960 (4) Å	θ = 3.8–13.7°
b = 5.723 (1) Å	µ = 0.08 mm^−1
c = 20.419 (4) Å	T = 296 K
β = 99.72 (2)°	Rhombohedral, white
V = 2068.8 (7) Å^3	0.62 × 0.18 × 0.12 mm
Z = 8

Data collection

Siemens P4 diffractometer	Rint = 0.024
Radiation source: normal-focus sealed tube	θmax = 25.3°, θmin = 2.0°
Graphite monochromator	h = 0→21
ω scans	k = 0→6
2229 measured reflections	l = −24→24
1873 independent reflections	3 standard reflections every 97 reflections
1057 reflections with I > 2σ(I)	intensity decay: 3.7%

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0407P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.81	(Δ/σ)max < 0.001
1873 reflections	Δρmax = 0.15 e Å^−3
145 parameters	Δρmin = −0.12 e Å^−3
2 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0065 (6)

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	0.34502 (9)	0.9466 (3)	0.34080 (8)	0.0533 (5)
N2	0.26994 (10)	0.7053 (3)	0.39203 (8)	0.0548 (5)
N3	0.31646 (10)	0.3312 (3)	0.43926 (8)	0.0545 (5)
N4	0.35483 (9)	0.5755 (3)	0.52878 (7)	0.0519 (5)
C1	0.38397 (12)	0.9842 (4)	0.29101 (11)	0.0626 (6)
H1	0.4082	1.1274	0.2901	0.075*
C2	0.39061 (12)	0.8288 (4)	0.24194 (10)	0.0598 (6)
H2	0.4189	0.8632	0.2090	0.072*
C3	0.35379 (11)	0.6187 (4)	0.24308 (9)	0.0563 (6)
H3	0.3561	0.5089	0.2099	0.068*
C4	0.31379 (10)	0.5705 (3)	0.29278 (8)	0.0474 (5)
H4	0.2891	0.4282	0.2940	0.057*
C5	0.31077 (10)	0.7390 (3)	0.34175 (8)	0.0439 (5)
C6	0.25273 (11)	0.4773 (4)	0.41543 (9)	0.0560 (6)
H6A	0.2237	0.4972	0.4510	0.067*
H6B	0.2208	0.3963	0.3795	0.067*
C7	0.36757 (10)	0.3840 (3)	0.49489 (9)	0.0450 (5)
C8	0.42917 (12)	0.2399 (4)	0.51489 (10)	0.0634 (6)
H8	0.4362	0.1063	0.4908	0.076*
C9	0.47930 (13)	0.2963 (5)	0.57024 (11)	0.0769 (7)
H9	0.5211	0.2018	0.5842	0.092*
C10	0.46790 (12)	0.4931 (5)	0.60536 (10)	0.0678 (7)
H10	0.5017	0.5355	0.6432	0.081*
C11	0.40581 (12)	0.6247 (4)	0.58340 (9)	0.0594 (6)
H11	0.3979	0.7574	0.6076	0.071*
H3N	0.3285 (10)	0.218 (2)	0.4145 (7)	0.052 (6)*
H2N	0.2787 (11)	0.816 (3)	0.4208 (8)	0.071 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0599 (11)	0.0466 (11)	0.0498 (10)	0.0070 (9)	−0.0009 (9)	−0.0027 (9)
N2	0.0667 (12)	0.0583 (13)	0.0398 (9)	0.0117 (10)	0.0105 (9)	−0.0058 (9)
N3	0.0631 (12)	0.0548 (12)	0.0442 (10)	0.0123 (10)	0.0055 (9)	−0.0085 (9)
N4	0.0518 (10)	0.0608 (11)	0.0419 (9)	0.0088 (9)	0.0040 (8)	−0.0087 (9)
C1	0.0571 (14)	0.0576 (15)	0.0696 (15)	−0.0041 (12)	0.0006 (12)	0.0066 (13)
C2	0.0565 (13)	0.0698 (16)	0.0544 (12)	0.0044 (12)	0.0137 (10)	0.0049 (12)
C3	0.0618 (14)	0.0615 (15)	0.0460 (12)	0.0097 (12)	0.0104 (10)	−0.0099 (11)
C4	0.0511 (12)	0.0480 (12)	0.0422 (11)	0.0011 (10)	0.0051 (9)	−0.0073 (10)
C5	0.0432 (11)	0.0486 (12)	0.0367 (10)	0.0121 (10)	−0.0023 (8)	−0.0021 (10)
C6	0.0517 (13)	0.0744 (15)	0.0409 (11)	0.0021 (12)	0.0051 (9)	−0.0027 (11)
C7	0.0501 (12)	0.0492 (12)	0.0379 (10)	0.0042 (10)	0.0137 (9)	0.0036 (10)
C8	0.0679 (14)	0.0611 (14)	0.0615 (13)	0.0224 (13)	0.0122 (12)	0.0027 (12)
C9	0.0590 (15)	0.098 (2)	0.0711 (15)	0.0319 (15)	0.0045 (13)	0.0125 (15)
C10	0.0535 (14)	0.0962 (19)	0.0491 (13)	0.0016 (14)	−0.0042 (11)	0.0021 (13)
C11	0.0624 (14)	0.0701 (15)	0.0452 (11)	0.0022 (13)	0.0072 (11)	−0.0076 (11)

Geometric parameters (Å, º)

N1—C5	1.339 (2)	C3—C4	1.367 (2)
N1—C1	1.345 (2)	C3—H3	0.9300
N2—C5	1.372 (2)	C4—C5	1.397 (2)
N2—C6	1.441 (2)	C4—H4	0.9300
N2—H2N	0.862 (9)	C6—H6A	0.9700
N3—C7	1.368 (2)	C6—H6B	0.9700
N3—C6	1.434 (2)	C7—C8	1.385 (3)
N3—H3N	0.872 (9)	C8—C9	1.360 (3)
N4—C7	1.336 (2)	C8—H8	0.9300
N4—C11	1.348 (2)	C9—C10	1.369 (3)
C1—C2	1.360 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.357 (3)
C2—C3	1.374 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—H11	0.9300
C5—N1—C1	116.84 (18)	N2—C5—C4	121.91 (19)
C5—N2—C6	123.16 (17)	N3—C6—N2	115.88 (17)
C5—N2—H2N	110.3 (14)	N3—C6—H6A	108.3
C6—N2—H2N	117.8 (14)	N2—C6—H6A	108.3
C7—N3—C6	122.55 (17)	N3—C6—H6B	108.3
C7—N3—H3N	116.6 (12)	N2—C6—H6B	108.3
C6—N3—H3N	119.9 (12)	H6A—C6—H6B	107.4
C7—N4—C11	116.61 (17)	N4—C7—N3	117.48 (17)
N1—C1—C2	125.0 (2)	N4—C7—C8	122.25 (18)
N1—C1—H1	117.5	N3—C7—C8	120.26 (19)
C2—C1—H1	117.5	C9—C8—C7	119.2 (2)
C1—C2—C3	117.2 (2)	C9—C8—H8	120.4
C1—C2—H2	121.4	C7—C8—H8	120.4
C3—C2—H2	121.4	C8—C9—C10	119.6 (2)
C4—C3—C2	120.26 (19)	C8—C9—H9	120.2
C4—C3—H3	119.9	C10—C9—H9	120.2
C2—C3—H3	119.9	C11—C10—C9	118.1 (2)
C3—C4—C5	118.74 (19)	C11—C10—H10	121.0
C3—C4—H4	120.6	C9—C10—H10	121.0
C5—C4—H4	120.6	N4—C11—C10	124.3 (2)
N1—C5—N2	116.13 (18)	N4—C11—H11	117.9
N1—C5—C4	121.91 (18)	C10—C11—H11	117.9
C5—N1—C1—C2	0.4 (3)	C5—N2—C6—N3	57.9 (2)
N1—C1—C2—C3	0.9 (3)	C11—N4—C7—N3	−179.96 (17)
C1—C2—C3—C4	−1.3 (3)	C11—N4—C7—C8	1.0 (3)
C2—C3—C4—C5	0.5 (3)	C6—N3—C7—N4	2.4 (3)
C1—N1—C5—N2	−178.66 (16)	C6—N3—C7—C8	−178.45 (17)
C1—N1—C5—C4	−1.3 (2)	N4—C7—C8—C9	−1.1 (3)
C6—N2—C5—N1	−157.00 (17)	N3—C7—C8—C9	179.82 (19)
C6—N2—C5—C4	25.6 (3)	C7—C8—C9—C10	0.3 (3)
C3—C4—C5—N1	0.9 (3)	C8—C9—C10—C11	0.5 (3)
C3—C4—C5—N2	178.10 (17)	C7—N4—C11—C10	−0.1 (3)
C7—N3—C6—N2	65.8 (2)	C9—C10—C11—N4	−0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1^i	0.87 (1)	2.22 (1)	3.082 (2)	172 (1)

Symmetry code: (i) x, y−1, z.