N,N′-Bis(4-pyridylmethyl­ene)benzene-1,4-diamine

Hou, Q.-F.; Ye, L.; Jiang, S.-M.

doi:10.1107/S1600536807002978

N,N′-Bis(4-pyridylmethylene)benzene-1,4-diamine

In the crystal structure of the title compound, C₁₈H₁₄N₄, there are two independent centrosymmetric molecules with different conformations. The two molecules are linked to each other via weak C—H

N hydrogen bonds and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807002978/xu2190sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807002978/xu2190Isup2.hkl Contains datablock I

CCDC reference: 618484

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.046
wR factor = 0.139
Data-to-parameter ratio = 16.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000)        3000 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C5      ..       5.12 su

   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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

N,N'-Bis(4-pyridylmethylene)benzene-1,4-diamine top

Crystal data top

C₁₈H₁₄N₄	Z = 2
M_r = 286.33	F(000) = 300
Triclinic, P1	D_x = 1.287 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5282 (15) Å	Cell parameters from 4360 reflections
b = 9.6334 (19) Å	θ = 3.0–27.5°
c = 10.975 (2) Å	µ = 0.08 mm⁻¹
α = 79.66 (3)°	T = 298 K
β = 81.89 (3)°	Block, yellow
γ = 71.31 (3)°	0.56 × 0.23 × 0.11 mm
V = 738.7 (3) Å³

Data collection top

Rigaku R-AXIS RAPID diffractometer	2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −9→9
6161 measured reflections	k = −12→11
3278 independent reflections	l = −14→14

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0662P)² + 0.0465P] where P = (F_o² + 2F_c²)/3
3278 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

4.8622 (0.0053) x + 6.6389 (0.0073) y + 7.9102 (0.0073) z = 4.2142 (0.0033)

* -0.0082 (0.0014) N1 * 0.0043 (0.0014) C1 * 0.0035 (0.0015) C2 * 0.0043 (0.0014) C3 * 0.0051 (0.0014) C4 * -0.0090 (0.0013) C5

Rms deviation of fitted atoms = 0.0061

0.2541 (0.0183) x + 9.2243 (0.0082) y + 1.5315 (0.0210) z = 0.7502 (0.0081)

Angle to previous plane (with approximate e.s.d.) = 58.23 (0.14)

* 0.0000 (0.0000) C7 * 0.0000 (0.0000) C8 * 0.0000 (0.0000) C9

Rms deviation of fitted atoms = 0.0000

5.8777 (0.0063) x - 3.1017 (0.0086) y + 1.9910 (0.0277) z = 0.4287 (0.0256)

Angle to previous plane (with approximate e.s.d.) = 54.66 (0.15)

* 0.0000 (0.0000) C16 * 0.0000 (0.0000) C17 * 0.0000 (0.0000) C18

Rms deviation of fitted atoms = 0.0000

7.0579 (0.0042) x + 5.4286 (0.0073) y + 4.1362 (0.0075) z = 6.5693 (0.0052)

Angle to previous plane (with approximate e.s.d.) = 53.29 (0.08)

* 0.0032 (0.0013) N3 * -0.0028 (0.0013) C10 * 0.0009 (0.0014) C11 * -0.0017 (0.0013) C12 * 0.0056 (0.0012) C13 * -0.0052 (0.0013) C14

Rms deviation of fitted atoms = 0.0037

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 (Å²) top

	x	y	z	U_iso*/U_eq
N4	0.10019 (18)	0.55151 (16)	0.74331 (13)	0.0424 (3)
C16	0.0522 (2)	0.52070 (18)	0.87244 (15)	0.0384 (4)
C15	0.1934 (2)	0.4478 (2)	0.68393 (16)	0.0474 (4)
H15	0.2299	0.3521	0.7267	0.057*
C12	0.1834 (2)	0.6076 (2)	0.47755 (17)	0.0483 (4)
H12	0.1005	0.6879	0.5125	0.058*
C18	−0.0252 (2)	0.40770 (19)	0.92487 (16)	0.0429 (4)
H18	−0.0435	0.3460	0.8748	0.051*
C17	0.0746 (2)	0.61232 (19)	0.94885 (15)	0.0424 (4)
H17	0.1241	0.6891	0.9143	0.051*
C13	0.2472 (2)	0.4708 (2)	0.54993 (16)	0.0432 (4)
N3	0.3631 (2)	0.5125 (2)	0.29678 (14)	0.0585 (4)
C14	0.3683 (3)	0.3554 (2)	0.49196 (18)	0.0529 (5)
H14	0.4129	0.2614	0.5366	0.064*
C11	0.4219 (3)	0.3825 (2)	0.36659 (19)	0.0575 (5)
H11	0.5045	0.3043	0.3289	0.069*
C10	0.2443 (3)	0.6224 (2)	0.35397 (17)	0.0539 (5)
H10	0.2002	0.7147	0.3066	0.065*
C5	0.4602 (2)	0.11867 (19)	0.14916 (16)	0.0416 (4)
N2	0.32047 (19)	0.01065 (17)	0.33696 (14)	0.0496 (4)
C7	0.1567 (2)	0.00761 (19)	0.41800 (16)	0.0458 (4)
C6	0.3040 (2)	0.1107 (2)	0.24486 (17)	0.0474 (4)
H6	0.1881	0.1830	0.2366	0.057*
N1	0.7475 (2)	0.1337 (2)	−0.03993 (16)	0.0580 (4)
C4	0.6265 (2)	0.0056 (2)	0.14357 (19)	0.0549 (5)
H4	0.6460	−0.0782	0.2033	0.066*
C1	0.5875 (2)	0.2441 (2)	−0.03269 (19)	0.0551 (5)
H1	0.5724	0.3277	−0.0925	0.066*
C9	0.1684 (2)	−0.0138 (2)	0.54477 (18)	0.0508 (5)
H9	0.2817	−0.0243	0.5755	0.061*
C8	−0.0125 (2)	0.0196 (2)	0.37390 (17)	0.0500 (5)
H8	−0.0209	0.0317	0.2887	0.060*
C3	0.4429 (2)	0.2406 (2)	0.05910 (18)	0.0535 (5)
H3	0.3337	0.3207	0.0602	0.064*
C2	0.7632 (3)	0.0174 (2)	0.0495 (2)	0.0634 (6)
H2	0.8744	−0.0608	0.0477	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N4	0.0476 (7)	0.0469 (9)	0.0302 (8)	−0.0150 (6)	−0.0004 (6)	0.0000 (6)
C16	0.0379 (8)	0.0425 (9)	0.0302 (8)	−0.0099 (6)	−0.0011 (6)	0.0006 (7)
C15	0.0553 (10)	0.0454 (10)	0.0364 (10)	−0.0140 (8)	0.0008 (8)	0.0007 (8)
C12	0.0523 (9)	0.0506 (11)	0.0381 (10)	−0.0129 (8)	−0.0012 (8)	−0.0033 (8)
C18	0.0474 (9)	0.0464 (10)	0.0354 (9)	−0.0151 (7)	−0.0028 (7)	−0.0063 (7)
C17	0.0472 (9)	0.0443 (10)	0.0368 (9)	−0.0202 (7)	0.0005 (7)	−0.0003 (7)
C13	0.0457 (9)	0.0507 (10)	0.0344 (9)	−0.0180 (7)	0.0002 (7)	−0.0063 (7)
N3	0.0682 (10)	0.0733 (12)	0.0350 (9)	−0.0243 (8)	0.0010 (7)	−0.0092 (8)
C14	0.0672 (11)	0.0452 (11)	0.0426 (11)	−0.0168 (8)	0.0043 (9)	−0.0040 (8)
C11	0.0691 (12)	0.0587 (13)	0.0432 (11)	−0.0173 (9)	0.0047 (9)	−0.0144 (9)
C10	0.0666 (11)	0.0574 (12)	0.0363 (10)	−0.0211 (9)	−0.0066 (8)	0.0029 (8)
C5	0.0421 (8)	0.0457 (10)	0.0359 (9)	−0.0170 (7)	0.0025 (7)	−0.0006 (7)
N2	0.0487 (8)	0.0503 (9)	0.0410 (9)	−0.0137 (6)	0.0086 (6)	0.0039 (7)
C7	0.0471 (9)	0.0431 (10)	0.0390 (10)	−0.0113 (7)	0.0069 (7)	0.0023 (7)
C6	0.0426 (8)	0.0493 (10)	0.0422 (10)	−0.0103 (7)	0.0055 (7)	0.0006 (8)
N1	0.0513 (9)	0.0669 (11)	0.0573 (11)	−0.0267 (8)	0.0127 (7)	−0.0101 (9)
C4	0.0496 (10)	0.0482 (11)	0.0572 (12)	−0.0097 (8)	0.0061 (9)	−0.0005 (9)
C1	0.0487 (9)	0.0658 (13)	0.0469 (11)	−0.0237 (8)	0.0019 (8)	0.0088 (9)
C9	0.0485 (9)	0.0545 (11)	0.0441 (11)	−0.0159 (8)	0.0025 (8)	0.0019 (8)
C8	0.0560 (10)	0.0519 (11)	0.0356 (10)	−0.0157 (8)	0.0032 (8)	0.0035 (8)
C3	0.0398 (9)	0.0605 (12)	0.0493 (11)	−0.0105 (8)	0.0017 (8)	0.0068 (9)
C2	0.0484 (10)	0.0547 (13)	0.0782 (16)	−0.0117 (8)	0.0159 (10)	−0.0108 (11)

Geometric parameters (Å, º) top

N4—C15	1.254 (2)	C5—C4	1.373 (2)
N4—C16	1.414 (2)	C5—C3	1.377 (3)
C16—C17	1.383 (2)	C5—C6	1.474 (2)
C16—C18	1.394 (2)	N2—C6	1.255 (2)
C15—C13	1.466 (2)	N2—C7	1.420 (2)
C15—H15	0.9300	C7—C9	1.381 (3)
C12—C10	1.366 (3)	C7—C8	1.390 (3)
C12—C13	1.387 (3)	C6—H6	0.9300
C12—H12	0.9300	N1—C1	1.331 (3)
C18—C17ⁱ	1.379 (2)	N1—C2	1.336 (3)
C18—H18	0.9300	C4—C2	1.368 (3)
C17—C18ⁱ	1.379 (2)	C4—H4	0.9300
C17—H17	0.9300	C1—C3	1.379 (2)
C13—C14	1.383 (2)	C1—H1	0.9300
N3—C11	1.322 (3)	C9—C8ⁱⁱ	1.381 (2)
N3—C10	1.337 (3)	C9—H9	0.9300
C14—C11	1.381 (3)	C8—C9ⁱⁱ	1.381 (2)
C14—H14	0.9300	C8—H8	0.9300
C11—H11	0.9300	C3—H3	0.9300
C10—H10	0.9300	C2—H2	0.9300

C15—N4—C16	119.67 (15)	C4—C5—C3	116.97 (16)
C17—C16—C18	118.80 (15)	C4—C5—C6	122.33 (17)
C17—C16—N4	117.99 (15)	C3—C5—C6	120.68 (16)
C18—C16—N4	123.13 (15)	C6—N2—C7	117.93 (16)
N4—C15—C13	122.83 (17)	C9—C7—C8	119.05 (16)
N4—C15—H15	118.6	C9—C7—N2	118.80 (17)
C13—C15—H15	118.6	C8—C7—N2	122.10 (16)
C10—C12—C13	118.89 (18)	N2—C6—C5	122.93 (16)
C10—C12—H12	120.6	N2—C6—H6	118.5
C13—C12—H12	120.6	C5—C6—H6	118.5
C17ⁱ—C18—C16	119.81 (16)	C1—N1—C2	115.93 (16)
C17ⁱ—C18—H18	120.1	C2—C4—C5	119.5 (2)
C16—C18—H18	120.1	C2—C4—H4	120.3
C18ⁱ—C17—C16	121.38 (16)	C5—C4—H4	120.3
C18ⁱ—C17—H17	119.3	N1—C1—C3	123.22 (19)
C16—C17—H17	119.3	N1—C1—H1	118.4
C14—C13—C12	117.71 (16)	C3—C1—H1	118.4
C14—C13—C15	120.26 (17)	C7—C9—C8ⁱⁱ	120.23 (18)
C12—C13—C15	122.01 (16)	C7—C9—H9	119.9
C11—N3—C10	116.35 (16)	C8ⁱⁱ—C9—H9	119.9
C11—C14—C13	118.73 (18)	C9ⁱⁱ—C8—C7	120.70 (17)
C11—C14—H14	120.6	C9ⁱⁱ—C8—H8	119.6
C13—C14—H14	120.6	C7—C8—H8	119.6
N3—C11—C14	124.13 (18)	C5—C3—C1	120.03 (17)
N3—C11—H11	117.9	C5—C3—H3	120.0
C14—C11—H11	117.9	C1—C3—H3	120.0
N3—C10—C12	124.17 (19)	N1—C2—C4	124.32 (18)
N3—C10—H10	117.9	N1—C2—H2	117.8
C12—C10—H10	117.9	C4—C2—H2	117.8

C15—N4—C16—C17	135.55 (17)	C6—N2—C7—C9	−135.0 (2)
C15—N4—C16—C18	−47.8 (2)	C6—N2—C7—C8	47.6 (2)
C16—N4—C15—C13	179.52 (15)	C7—N2—C6—C5	−175.23 (17)
C17—C16—C18—C17ⁱ	−1.1 (3)	C4—C5—C6—N2	10.0 (3)
N4—C16—C18—C17ⁱ	−177.69 (14)	C3—C5—C6—N2	−171.34 (19)
C18—C16—C17—C18ⁱ	1.1 (3)	C3—C5—C4—C2	−1.3 (3)
N4—C16—C17—C18ⁱ	177.89 (14)	C6—C5—C4—C2	177.42 (18)
C10—C12—C13—C14	−0.8 (3)	C2—N1—C1—C3	−1.2 (3)
C10—C12—C13—C15	177.80 (16)	C8—C7—C9—C8ⁱⁱ	−1.5 (3)
N4—C15—C13—C14	172.39 (17)	N2—C7—C9—C8ⁱⁱ	−178.98 (18)
N4—C15—C13—C12	−6.1 (3)	C9—C7—C8—C9ⁱⁱ	1.5 (3)
C12—C13—C14—C11	1.1 (3)	N2—C7—C8—C9ⁱⁱ	178.91 (18)
C15—C13—C14—C11	−177.49 (17)	C4—C5—C3—C1	1.3 (3)
C10—N3—C11—C14	−0.1 (3)	C6—C5—C3—C1	−177.51 (18)
C13—C14—C11—N3	−0.7 (3)	N1—C1—C3—C5	0.0 (3)
C11—N3—C10—C12	0.5 (3)	C1—N1—C2—C4	1.1 (3)
C13—C12—C10—N3	0.0 (3)	C5—C4—C2—N1	0.2 (3)

Symmetry codes: (i) −x, −y+1, −z+2; (ii) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···N3ⁱⁱⁱ	0.93	2.56	3.443 (3)	158

Symmetry code: (iii) −x+1, −y+1, −z.

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N,N′-Bis(4-pyridylmethyl­ene)benzene-1,4-diamine

Supporting information

Key indicators

checkCIF/PLATON results

N,N′-Bis(4-pyridylmethylene)benzene-1,4-diamine