(3Z,5E)-2-Amino-4,6-bis(pyridin-3-yl)hepta-1,3,5-triene-1,1,3-tricarbo­nitrile

Cai, C.; Lin, B.; Wu, W.; Zhu, Q.

doi:10.1107/S2414314620012468

(3Z,5E)-2-Amino-4,6-bis(pyridin-3-yl)hepta-1,3,5-triene-1,1,3-tricarbonitrile

C. Cai, B. Lin, W. Wu and Q. Zhu

In the title compound, C₂₀H₁₄N₆, the dihedral angle between the pyridine rings is 37.98 (7)°. In the crystal, N—H

N hydrogen bonds link the molecules into (10 $\overline{2}$ ) sheets.

Keywords: crystal structure; pyridine ring; dicyano.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314620012468/hb4363sup1.cif Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2414314620012468/hb4363Isup3.hkl Contains datablock I

CCDC reference: 2020071

checkCIF report

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level C
PLAT193_ALERT_1_C Cell and Diffraction Temperatures Differ by ....          3 Degree

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group  P21/c        P21/n Note
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C1       --C2       .        6.7 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C2       --C3       .        7.3 s.u.
PLAT230_ALERT_2_G Hirshfeld Test Diff for    C5       --C6       .        8.3 s.u.
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        264 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.6 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         10 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: olex2.solve (Bourhis et al., 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

(3Z,5E)-2-Amino-4,6-bis(pyridin-3-yl)hepta-1,3,5-triene-1,1,3-tricarbonitrile top

Crystal data top

C₂₀H₁₄N₆	F(000) = 704
M_r = 338.37	D_x = 1.236 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.4636 (13) Å	Cell parameters from 7944 reflections
b = 9.8402 (15) Å	θ = 2.3–27.2°
c = 22.701 (3) Å	µ = 0.08 mm⁻¹
β = 105.917 (5)°	T = 296 K
V = 1818.1 (5) Å³	Block, yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker APEXII CCD diffractometer	3314 reflections with I > 2σ(I)
ω scans	R_int = 0.043
Absorption correction: multi-scan (SADABS; Bruker, 2013)	θ_max = 27.5°, θ_min = 1.9°
T_min = 0.593, T_max = 0.746	h = −11→10
14113 measured reflections	k = −12→12
3912 independent reflections	l = −28→28

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.0519P)² + 0.4095P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
3912 reflections	Δρ_max = 0.24 e Å⁻³
236 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The C-bound H atoms were geometrically placed (C—H = 0.93–0.96 Å) and refined as riding atoms. The N-bound H atoms were located in difference maps and refined as riding atoms in their as-found relative positions.

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

	x	y	z	U_iso*/U_eq
N1	0.56958 (17)	0.53555 (15)	0.42295 (5)	0.0603 (4)
N2	0.94585 (16)	0.23652 (13)	0.49739 (6)	0.0549 (3)
N3	0.79713 (13)	0.65640 (10)	0.57511 (5)	0.0390 (2)
H3A	0.741712	0.707730	0.544186	0.047*
H3B	0.814112	0.687880	0.612586	0.047*
N4	1.21602 (16)	0.64094 (15)	0.67229 (7)	0.0643 (4)
N5	1.19544 (15)	0.19840 (13)	0.79606 (5)	0.0520 (3)
N6	0.35370 (14)	0.13699 (12)	0.52035 (6)	0.0500 (3)
C1	0.67660 (15)	0.50431 (13)	0.46360 (5)	0.0388 (3)
C2	0.80838 (14)	0.46093 (12)	0.51396 (5)	0.0325 (2)
C3	0.88674 (15)	0.33700 (13)	0.50564 (5)	0.0375 (3)
C4	0.85396 (13)	0.53460 (11)	0.56833 (5)	0.0313 (2)
C5	0.97970 (14)	0.47672 (12)	0.62215 (5)	0.0337 (3)
C6	1.11384 (15)	0.56647 (14)	0.64999 (6)	0.0410 (3)
C7	0.96757 (14)	0.35134 (12)	0.64586 (5)	0.0343 (3)
C8	1.10641 (15)	0.29486 (13)	0.69512 (5)	0.0369 (3)
C9	1.26451 (16)	0.28301 (16)	0.68862 (6)	0.0492 (3)
H9	1.288538	0.312862	0.653171	0.059*
C10	1.38551 (18)	0.22577 (18)	0.73606 (7)	0.0580 (4)
H10	1.491932	0.215363	0.732728	0.070*
C11	1.34588 (19)	0.18459 (16)	0.78815 (6)	0.0556 (4)
H11	1.427618	0.145165	0.819473	0.067*
C12	1.07878 (16)	0.25103 (14)	0.74965 (6)	0.0432 (3)
H12	0.973100	0.258789	0.754047	0.052*
C13	0.81217 (14)	0.27732 (13)	0.62629 (5)	0.0366 (3)
H13	0.718338	0.331166	0.615438	0.044*
C14	0.78551 (15)	0.14270 (13)	0.62173 (6)	0.0410 (3)
C15	0.9134 (2)	0.03265 (16)	0.63531 (9)	0.0667 (5)
H15A	1.019436	0.071646	0.638498	0.100*
H15B	0.888321	−0.033182	0.602860	0.100*
H15C	0.914337	−0.010841	0.673256	0.100*
C16	0.61170 (16)	0.09860 (13)	0.59646 (6)	0.0415 (3)
C17	0.53955 (19)	−0.00536 (16)	0.62118 (7)	0.0566 (4)
H17	0.601159	−0.054456	0.654636	0.068*
C18	0.3753 (2)	−0.03560 (16)	0.59575 (8)	0.0622 (4)
H18	0.325133	−0.104969	0.611867	0.075*
C19	0.28733 (18)	0.03862 (15)	0.54626 (8)	0.0557 (4)
H19	0.176290	0.019311	0.530079	0.067*
C20	0.51241 (16)	0.16395 (14)	0.54536 (6)	0.0440 (3)
H20	0.560161	0.231478	0.527256	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0603 (8)	0.0704 (9)	0.0382 (6)	0.0141 (7)	−0.0065 (6)	−0.0033 (6)
N2	0.0563 (7)	0.0427 (7)	0.0675 (8)	0.0025 (6)	0.0203 (6)	−0.0034 (6)
N3	0.0455 (6)	0.0360 (5)	0.0295 (5)	0.0030 (4)	0.0003 (4)	0.0003 (4)
N4	0.0456 (7)	0.0640 (9)	0.0725 (9)	−0.0165 (6)	−0.0019 (6)	−0.0138 (7)
N5	0.0559 (7)	0.0589 (7)	0.0328 (5)	0.0047 (6)	−0.0018 (5)	0.0094 (5)
N6	0.0394 (6)	0.0452 (6)	0.0561 (7)	−0.0040 (5)	−0.0027 (5)	0.0045 (5)
C1	0.0417 (7)	0.0415 (7)	0.0301 (6)	−0.0004 (5)	0.0047 (5)	−0.0034 (5)
C2	0.0317 (6)	0.0340 (6)	0.0290 (5)	−0.0029 (5)	0.0038 (4)	0.0014 (4)
C3	0.0359 (6)	0.0386 (7)	0.0367 (6)	−0.0054 (5)	0.0076 (5)	0.0005 (5)
C4	0.0294 (5)	0.0324 (6)	0.0294 (5)	−0.0051 (4)	0.0033 (4)	0.0038 (4)
C5	0.0287 (6)	0.0379 (6)	0.0297 (5)	−0.0033 (5)	−0.0002 (4)	0.0001 (4)
C6	0.0346 (6)	0.0438 (7)	0.0390 (6)	−0.0025 (5)	0.0008 (5)	0.0001 (5)
C7	0.0319 (6)	0.0384 (6)	0.0287 (5)	0.0009 (5)	0.0020 (4)	0.0035 (5)
C8	0.0340 (6)	0.0392 (6)	0.0316 (6)	−0.0002 (5)	−0.0008 (5)	0.0038 (5)
C9	0.0396 (7)	0.0625 (9)	0.0423 (7)	0.0063 (6)	0.0059 (6)	0.0091 (6)
C10	0.0381 (7)	0.0731 (10)	0.0559 (9)	0.0140 (7)	0.0014 (6)	0.0050 (7)
C11	0.0521 (8)	0.0585 (9)	0.0422 (7)	0.0135 (7)	−0.0105 (6)	0.0059 (6)
C12	0.0404 (7)	0.0509 (8)	0.0337 (6)	0.0014 (6)	0.0025 (5)	0.0062 (5)
C13	0.0317 (6)	0.0393 (6)	0.0343 (6)	0.0004 (5)	0.0015 (5)	0.0092 (5)
C14	0.0362 (6)	0.0399 (7)	0.0412 (6)	−0.0013 (5)	0.0007 (5)	0.0100 (5)
C15	0.0485 (9)	0.0434 (8)	0.0924 (12)	0.0043 (7)	−0.0072 (8)	0.0069 (8)
C16	0.0387 (7)	0.0349 (6)	0.0461 (7)	−0.0031 (5)	0.0036 (5)	0.0055 (5)
C17	0.0525 (8)	0.0470 (8)	0.0626 (9)	−0.0076 (7)	0.0026 (7)	0.0190 (7)
C18	0.0535 (9)	0.0503 (9)	0.0794 (11)	−0.0157 (7)	0.0123 (8)	0.0137 (8)
C19	0.0400 (7)	0.0483 (8)	0.0722 (10)	−0.0092 (6)	0.0043 (7)	−0.0005 (7)
C20	0.0396 (7)	0.0400 (7)	0.0466 (7)	−0.0050 (5)	0.0018 (5)	0.0064 (6)

Geometric parameters (Å, º) top

N1—C1	1.1438 (16)	C9—C10	1.3859 (19)
N2—C3	1.1465 (17)	C10—H10	0.9300
N3—H3A	0.8873	C10—C11	1.376 (2)
N3—H3B	0.8795	C11—H11	0.9300
N3—C4	1.3161 (15)	C12—H12	0.9300
N4—C6	1.1407 (18)	C13—H13	0.9300
N5—C11	1.341 (2)	C13—C14	1.3430 (18)
N5—C12	1.3352 (16)	C14—C15	1.502 (2)
N6—C19	1.3341 (19)	C14—C16	1.4894 (18)
N6—C20	1.3337 (17)	C15—H15A	0.9600
C1—C2	1.4261 (16)	C15—H15B	0.9600
C2—C3	1.4253 (17)	C15—H15C	0.9600
C2—C4	1.3915 (16)	C16—C17	1.3865 (19)
C4—C5	1.4956 (15)	C16—C20	1.3895 (18)
C5—C6	1.4403 (17)	C17—H17	0.9300
C5—C7	1.3611 (17)	C17—C18	1.384 (2)
C7—C8	1.4898 (15)	C18—H18	0.9300
C7—C13	1.4619 (16)	C18—C19	1.375 (2)
C8—C9	1.3908 (18)	C19—H19	0.9300
C8—C12	1.3898 (17)	C20—H20	0.9300
C9—H9	0.9300

H3A—N3—H3B	118.4	C10—C11—H11	118.3
C4—N3—H3A	123.8	N5—C12—C8	123.68 (13)
C4—N3—H3B	117.8	N5—C12—H12	118.2
C12—N5—C11	117.23 (12)	C8—C12—H12	118.2
C20—N6—C19	116.96 (12)	C7—C13—H13	115.4
N1—C1—C2	178.16 (15)	C14—C13—C7	129.28 (12)
C3—C2—C1	116.10 (10)	C14—C13—H13	115.4
C4—C2—C1	121.38 (11)	C13—C14—C15	126.78 (12)
C4—C2—C3	122.50 (10)	C13—C14—C16	116.38 (11)
N2—C3—C2	177.90 (14)	C16—C14—C15	116.69 (12)
N3—C4—C2	123.83 (10)	C14—C15—H15A	109.5
N3—C4—C5	116.89 (10)	C14—C15—H15B	109.5
C2—C4—C5	119.23 (10)	C14—C15—H15C	109.5
C6—C5—C4	115.06 (10)	H15A—C15—H15B	109.5
C7—C5—C4	123.66 (10)	H15A—C15—H15C	109.5
C7—C5—C6	121.21 (10)	H15B—C15—H15C	109.5
N4—C6—C5	177.52 (15)	C17—C16—C14	123.86 (12)
C5—C7—C8	120.36 (10)	C17—C16—C20	116.53 (12)
C5—C7—C13	119.38 (10)	C20—C16—C14	119.61 (11)
C13—C7—C8	120.07 (10)	C16—C17—H17	120.2
C9—C8—C7	122.37 (11)	C18—C17—C16	119.57 (13)
C12—C8—C7	119.57 (11)	C18—C17—H17	120.2
C12—C8—C9	118.05 (11)	C17—C18—H18	120.5
C8—C9—H9	120.7	C19—C18—C17	118.91 (14)
C10—C9—C8	118.62 (13)	C19—C18—H18	120.5
C10—C9—H9	120.7	N6—C19—C18	123.14 (13)
C9—C10—H10	120.5	N6—C19—H19	118.4
C11—C10—C9	119.03 (14)	C18—C19—H19	118.4
C11—C10—H10	120.5	N6—C20—C16	124.84 (12)
N5—C11—C10	123.35 (12)	N6—C20—H20	117.6
N5—C11—H11	118.3	C16—C20—H20	117.6

N3—C4—C5—C6	−48.83 (14)	C8—C9—C10—C11	−0.9 (2)
N3—C4—C5—C7	128.18 (13)	C9—C8—C12—N5	0.1 (2)
C1—C2—C4—N3	−9.54 (18)	C9—C10—C11—N5	−0.9 (3)
C1—C2—C4—C5	173.02 (11)	C11—N5—C12—C8	−1.8 (2)
C2—C4—C5—C6	128.78 (12)	C12—N5—C11—C10	2.2 (2)
C2—C4—C5—C7	−54.20 (16)	C12—C8—C9—C10	1.3 (2)
C3—C2—C4—N3	172.02 (11)	C13—C7—C8—C9	129.94 (14)
C3—C2—C4—C5	−5.42 (17)	C13—C7—C8—C12	−49.56 (17)
C4—C5—C7—C8	173.26 (11)	C13—C14—C16—C17	−135.69 (15)
C4—C5—C7—C13	−11.86 (18)	C13—C14—C16—C20	43.89 (18)
C5—C7—C8—C9	−55.22 (18)	C14—C16—C17—C18	177.62 (15)
C5—C7—C8—C12	125.28 (13)	C14—C16—C20—N6	−177.12 (14)
C5—C7—C13—C14	149.68 (13)	C15—C14—C16—C17	48.4 (2)
C6—C5—C7—C8	−9.90 (18)	C15—C14—C16—C20	−132.01 (15)
C6—C5—C7—C13	164.97 (11)	C16—C17—C18—C19	0.1 (3)
C7—C8—C9—C10	−178.20 (13)	C17—C16—C20—N6	2.5 (2)
C7—C8—C12—N5	179.59 (13)	C17—C18—C19—N6	1.6 (3)
C7—C13—C14—C15	−0.9 (2)	C19—N6—C20—C16	−0.9 (2)
C7—C13—C14—C16	−176.34 (11)	C20—N6—C19—C18	−1.2 (2)
C8—C7—C13—C14	−35.42 (19)	C20—C16—C17—C18	−2.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N6ⁱ	0.89	2.12	2.9903 (17)	168
N3—H3B···N5ⁱⁱ	0.88	2.10	2.9372 (16)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.

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(3Z,5E)-2-Amino-4,6-bis(pyridin-3-yl)hepta-1,3,5-triene-1,1,3-tricarbo­nitrile

Supporting information

checkCIF/PLATON results

(3Z,5E)-2-Amino-4,6-bis(pyridin-3-yl)hepta-1,3,5-triene-1,1,3-tricarbonitrile