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The title 2,3′-bi­pyridine-based quaterpyridine derivative has a linear geometry. The pyridine rings are tilted slightly with respect to each other. In the crystal, π–π stacking and weak C—H...π inter­actions lead to formation of a two-dimensional layer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S205698901901274X/su5516sup1.cif
Contains datablocks I, New_Global_Publ_Block

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S205698901901274X/su5516Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S205698901901274X/su5516Isup3.cml
Supplementary material

CCDC reference: 1953451

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.054
  • wR factor = 0.160
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.14 Report PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 --C1 . 6.5 s.u.
Alert level G PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 14 Note PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 12 Info
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 2 ALERT level C = Check. Ensure it is not caused by an omission or oversight 2 ALERT level G = General information/check it is not something unexpected 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

2,2''',6,6'''-Tetramethoxy-3,2':5',3'':6'',3'''-quaterpyridine top
Crystal data top
C24H22N4O4F(000) = 904
Mr = 430.45Dx = 1.402 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 7.9556 (6) ÅCell parameters from 5328 reflections
b = 14.8583 (11) Åθ = 2.6–27.8°
c = 17.3362 (12) ŵ = 0.10 mm1
β = 95.556 (4)°T = 223 K
V = 2039.6 (3) Å3Plate, yellow
Z = 40.25 × 0.24 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
3739 reflections with I > 2σ(I)
φ and ω scansRint = 0.030
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
θmax = 28.4°, θmin = 1.8°
Tmin = 0.673, Tmax = 0.746h = 1010
19298 measured reflectionsk = 1719
5090 independent reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0773P)2 + 0.5757P]
where P = (Fo2 + 2Fc2)/3
5090 reflections(Δ/σ)max < 0.001
289 parametersΔρmax = 0.52 e Å3
0 restraintsΔρmin = 0.24 e Å3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.95531 (17)0.30630 (8)0.18517 (7)0.0449 (3)
O21.11979 (18)0.05085 (9)0.06420 (7)0.0518 (3)
O30.3179 (2)0.49944 (9)0.92984 (8)0.0598 (4)
O40.34148 (15)0.25399 (7)0.77125 (7)0.0414 (3)
N11.03508 (18)0.17731 (10)0.12555 (8)0.0393 (3)
N20.8189 (2)0.15075 (10)0.37266 (9)0.0473 (4)
N30.5594 (2)0.41616 (10)0.60438 (8)0.0446 (4)
N40.33254 (18)0.37725 (10)0.84952 (8)0.0394 (3)
C10.9663 (2)0.21499 (11)0.18490 (9)0.0384 (4)
C21.0519 (2)0.08936 (12)0.12445 (10)0.0417 (4)
C31.0021 (2)0.03287 (13)0.18274 (11)0.0464 (4)
H31.01690.02990.18120.056*
C40.9309 (2)0.07415 (11)0.24195 (10)0.0391 (4)
H40.89530.03820.28190.047*
C50.9084 (2)0.16701 (12)0.24608 (9)0.0385 (4)
C60.8322 (2)0.20736 (12)0.31288 (9)0.0378 (4)
C70.7761 (2)0.29583 (12)0.31670 (10)0.0426 (4)
H70.78400.33470.27440.051*
C80.7093 (2)0.32678 (12)0.38209 (10)0.0416 (4)
H80.67300.38680.38450.050*
C90.6954 (2)0.26934 (11)0.44454 (9)0.0362 (4)
C100.7519 (2)0.18211 (13)0.43460 (10)0.0461 (4)
H100.74200.14150.47550.055*
C110.6163 (2)0.38702 (12)0.53909 (10)0.0454 (4)
H110.65300.43060.50520.055*
C120.6258 (2)0.29739 (11)0.51692 (9)0.0352 (3)
C130.5675 (2)0.23564 (12)0.56830 (10)0.0443 (4)
H130.56920.17390.55670.053*
C140.5075 (2)0.26401 (12)0.63572 (10)0.0441 (4)
H140.46720.22170.66980.053*
C150.5059 (2)0.35488 (11)0.65387 (9)0.0350 (3)
C160.4526 (2)0.39106 (11)0.72707 (9)0.0363 (4)
C170.4828 (3)0.48144 (12)0.74535 (11)0.0464 (4)
H170.53510.51790.71030.056*
C180.4387 (3)0.51856 (13)0.81250 (12)0.0564 (5)
H180.45920.57960.82410.068*
C190.3625 (2)0.46282 (12)0.86309 (10)0.0455 (4)
C200.3758 (2)0.34235 (11)0.78363 (9)0.0350 (4)
C211.0326 (3)0.35294 (14)0.12610 (11)0.0546 (5)
H21A1.01690.41720.13200.082*
H21B1.15240.33930.13040.082*
H21C0.98130.33400.07570.082*
C221.1533 (3)0.10987 (14)0.00148 (10)0.0497 (5)
H22A1.20170.07550.03850.075*
H22B1.04870.13750.02000.075*
H22C1.23210.15630.02080.075*
C230.2306 (3)0.44212 (15)0.97894 (12)0.0624 (6)
H23A0.20540.47531.02460.094*
H23B0.12610.42150.95100.094*
H23C0.30100.39070.99450.094*
C240.2705 (2)0.20561 (12)0.83165 (11)0.0444 (4)
H24A0.25180.14350.81590.067*
H24B0.34770.20770.87850.067*
H24C0.16380.23280.84150.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0596 (8)0.0332 (6)0.0437 (7)0.0006 (5)0.0152 (6)0.0045 (5)
O20.0633 (9)0.0451 (7)0.0486 (7)0.0003 (6)0.0136 (6)0.0066 (6)
O30.0871 (11)0.0448 (8)0.0512 (8)0.0013 (7)0.0261 (7)0.0053 (6)
O40.0477 (7)0.0327 (6)0.0458 (7)0.0051 (5)0.0141 (5)0.0031 (5)
N10.0379 (8)0.0435 (8)0.0362 (7)0.0006 (6)0.0031 (6)0.0048 (6)
N20.0558 (10)0.0450 (9)0.0424 (8)0.0017 (7)0.0119 (7)0.0060 (6)
N30.0571 (9)0.0351 (8)0.0430 (8)0.0065 (7)0.0125 (7)0.0027 (6)
N40.0404 (8)0.0381 (8)0.0402 (7)0.0044 (6)0.0060 (6)0.0037 (6)
C10.0378 (9)0.0381 (9)0.0388 (8)0.0010 (7)0.0008 (7)0.0019 (7)
C20.0391 (9)0.0436 (10)0.0422 (9)0.0023 (7)0.0028 (7)0.0034 (7)
C30.0482 (10)0.0397 (9)0.0516 (10)0.0002 (8)0.0056 (8)0.0033 (8)
C40.0404 (9)0.0364 (9)0.0409 (9)0.0018 (7)0.0062 (7)0.0055 (7)
C50.0361 (9)0.0390 (9)0.0399 (9)0.0020 (7)0.0016 (7)0.0026 (7)
C60.0319 (8)0.0440 (9)0.0371 (8)0.0014 (7)0.0021 (6)0.0030 (7)
C70.0449 (10)0.0464 (10)0.0374 (8)0.0006 (8)0.0084 (7)0.0101 (7)
C80.0433 (10)0.0393 (9)0.0433 (9)0.0033 (7)0.0100 (7)0.0065 (7)
C90.0310 (8)0.0426 (9)0.0352 (8)0.0032 (7)0.0036 (6)0.0041 (7)
C100.0547 (11)0.0435 (10)0.0412 (9)0.0031 (8)0.0111 (8)0.0085 (7)
C110.0563 (11)0.0381 (9)0.0437 (9)0.0079 (8)0.0140 (8)0.0069 (7)
C120.0313 (8)0.0390 (9)0.0353 (8)0.0020 (6)0.0025 (6)0.0041 (6)
C130.0553 (11)0.0335 (9)0.0464 (9)0.0007 (8)0.0159 (8)0.0032 (7)
C140.0549 (11)0.0367 (9)0.0429 (9)0.0002 (8)0.0158 (8)0.0076 (7)
C150.0322 (8)0.0363 (8)0.0364 (8)0.0005 (6)0.0029 (6)0.0043 (6)
C160.0364 (8)0.0340 (8)0.0383 (8)0.0008 (7)0.0029 (7)0.0048 (6)
C170.0615 (12)0.0349 (9)0.0445 (9)0.0049 (8)0.0138 (8)0.0045 (7)
C180.0851 (15)0.0332 (9)0.0532 (11)0.0053 (9)0.0175 (10)0.0028 (8)
C190.0563 (11)0.0398 (10)0.0416 (9)0.0041 (8)0.0103 (8)0.0008 (7)
C200.0318 (8)0.0328 (8)0.0402 (8)0.0032 (6)0.0023 (6)0.0038 (6)
C210.0740 (14)0.0475 (11)0.0449 (10)0.0004 (9)0.0183 (9)0.0089 (8)
C220.0585 (12)0.0524 (11)0.0399 (9)0.0001 (9)0.0129 (8)0.0029 (8)
C230.0874 (16)0.0519 (12)0.0522 (11)0.0038 (11)0.0292 (11)0.0029 (9)
C240.0453 (10)0.0396 (9)0.0500 (10)0.0034 (8)0.0134 (8)0.0097 (7)
Geometric parameters (Å, º) top
O1—C11.359 (2)C9—C121.480 (2)
O1—C211.425 (2)C10—H100.9400
O2—C21.349 (2)C11—C121.390 (2)
O2—C221.442 (2)C11—H110.9400
O3—C191.357 (2)C12—C131.389 (2)
O3—C231.431 (2)C13—C141.371 (2)
O4—C201.3538 (19)C13—H130.9400
O4—C241.4308 (19)C14—C151.387 (2)
N1—C21.314 (2)C14—H140.9400
N1—C11.334 (2)C15—C161.478 (2)
N2—C101.328 (2)C16—C171.395 (2)
N2—C61.347 (2)C16—C201.405 (2)
N3—C111.331 (2)C17—C181.364 (3)
N3—C151.348 (2)C17—H170.9400
N4—C191.311 (2)C18—C191.388 (3)
N4—C201.330 (2)C18—H180.9400
C1—C51.393 (2)C21—H21A0.9700
C2—C31.400 (3)C21—H21B0.9700
C3—C41.365 (2)C21—H21C0.9700
C3—H30.9400C22—H22A0.9700
C4—C51.394 (2)C22—H22B0.9700
C4—H40.9400C22—H22C0.9700
C5—C61.485 (2)C23—H23A0.9700
C6—C71.392 (3)C23—H23B0.9700
C7—C81.377 (2)C23—H23C0.9700
C7—H70.9400C24—H24A0.9700
C8—C91.391 (2)C24—H24B0.9700
C8—H80.9400C24—H24C0.9700
C9—C101.388 (3)
C1—O1—C21116.78 (14)C12—C13—H13119.7
C2—O2—C22116.31 (14)C13—C14—C15120.29 (16)
C19—O3—C23116.79 (15)C13—C14—H14119.9
C20—O4—C24117.33 (13)C15—C14—H14119.9
C2—N1—C1118.58 (15)N3—C15—C14120.19 (15)
C10—N2—C6118.06 (15)N3—C15—C16115.81 (14)
C11—N3—C15118.40 (15)C14—C15—C16123.97 (15)
C19—N4—C20118.35 (15)C17—C16—C20114.46 (15)
N1—C1—O1116.91 (15)C17—C16—C15119.20 (15)
N1—C1—C5124.26 (16)C20—C16—C15126.31 (15)
O1—C1—C5118.82 (15)C18—C17—C16122.02 (17)
N1—C2—O2118.82 (16)C18—C17—H17119.0
N1—C2—C3123.33 (16)C16—C17—H17119.0
O2—C2—C3117.84 (16)C17—C18—C19117.52 (17)
C4—C3—C2116.12 (16)C17—C18—H18121.2
C4—C3—H3121.9C19—C18—H18121.2
C2—C3—H3121.9N4—C19—O3118.96 (16)
C3—C4—C5123.24 (16)N4—C19—C18123.26 (17)
C3—C4—H4118.4O3—C19—C18117.77 (17)
C5—C4—H4118.4N4—C20—O4116.70 (14)
C1—C5—C4114.45 (15)N4—C20—C16124.38 (15)
C1—C5—C6125.27 (16)O4—C20—C16118.91 (14)
C4—C5—C6120.26 (15)O1—C21—H21A109.5
N2—C6—C7120.26 (16)O1—C21—H21B109.5
N2—C6—C5114.61 (15)H21A—C21—H21B109.5
C7—C6—C5125.12 (15)O1—C21—H21C109.5
C8—C7—C6120.37 (16)H21A—C21—H21C109.5
C8—C7—H7119.8H21B—C21—H21C109.5
C6—C7—H7119.8O2—C22—H22A109.5
C7—C8—C9120.13 (16)O2—C22—H22B109.5
C7—C8—H8119.9H22A—C22—H22B109.5
C9—C8—H8119.9O2—C22—H22C109.5
C10—C9—C8115.14 (15)H22A—C22—H22C109.5
C10—C9—C12121.38 (15)H22B—C22—H22C109.5
C8—C9—C12123.48 (15)O3—C23—H23A109.5
N2—C10—C9126.02 (16)O3—C23—H23B109.5
N2—C10—H10117.0H23A—C23—H23B109.5
C9—C10—H10117.0O3—C23—H23C109.5
N3—C11—C12125.36 (16)H23A—C23—H23C109.5
N3—C11—H11117.3H23B—C23—H23C109.5
C12—C11—H11117.3O4—C24—H24A109.5
C13—C12—C11115.14 (15)O4—C24—H24B109.5
C13—C12—C9122.22 (15)H24A—C24—H24B109.5
C11—C12—C9122.63 (15)O4—C24—H24C109.5
C14—C13—C12120.59 (16)H24A—C24—H24C109.5
C14—C13—H13119.7H24B—C24—H24C109.5
C2—N1—C1—O1178.19 (15)N3—C11—C12—C9178.07 (17)
C2—N1—C1—C50.8 (2)C10—C9—C12—C1319.2 (3)
C21—O1—C1—N15.8 (2)C8—C9—C12—C13160.80 (17)
C21—O1—C1—C5173.33 (16)C10—C9—C12—C11159.83 (17)
C1—N1—C2—O2179.34 (15)C8—C9—C12—C1120.2 (3)
C1—N1—C2—C30.4 (3)C11—C12—C13—C140.6 (3)
C22—O2—C2—N16.0 (2)C9—C12—C13—C14178.47 (17)
C22—O2—C2—C3173.76 (16)C12—C13—C14—C150.7 (3)
N1—C2—C3—C41.0 (3)C11—N3—C15—C141.3 (3)
O2—C2—C3—C4178.75 (15)C11—N3—C15—C16176.97 (15)
C2—C3—C4—C50.4 (3)C13—C14—C15—N31.7 (3)
N1—C1—C5—C41.3 (2)C13—C14—C15—C16176.46 (17)
O1—C1—C5—C4177.71 (15)N3—C15—C16—C179.1 (2)
N1—C1—C5—C6179.71 (15)C14—C15—C16—C17169.13 (18)
O1—C1—C5—C60.7 (2)N3—C15—C16—C20172.75 (15)
C3—C4—C5—C10.6 (2)C14—C15—C16—C209.0 (3)
C3—C4—C5—C6179.12 (16)C20—C16—C17—C180.7 (3)
C10—N2—C6—C70.3 (3)C15—C16—C17—C18179.08 (18)
C10—N2—C6—C5179.94 (16)C16—C17—C18—C190.3 (3)
C1—C5—C6—N2166.43 (16)C20—N4—C19—O3179.54 (16)
C4—C5—C6—N211.9 (2)C20—N4—C19—C180.7 (3)
C1—C5—C6—C713.8 (3)C23—O3—C19—N43.8 (3)
C4—C5—C6—C7167.89 (17)C23—O3—C19—C18176.41 (19)
N2—C6—C7—C81.1 (3)C17—C18—C19—N40.4 (3)
C5—C6—C7—C8179.12 (16)C17—C18—C19—O3179.80 (19)
C6—C7—C8—C90.8 (3)C19—N4—C20—O4179.38 (15)
C7—C8—C9—C100.3 (2)C19—N4—C20—C160.2 (2)
C7—C8—C9—C12179.71 (16)C24—O4—C20—N43.2 (2)
C6—N2—C10—C91.0 (3)C24—O4—C20—C16177.18 (15)
C8—C9—C10—N21.2 (3)C17—C16—C20—N40.5 (2)
C12—C9—C10—N2178.79 (17)C15—C16—C20—N4178.68 (15)
C15—N3—C11—C120.0 (3)C17—C16—C20—O4179.93 (15)
N3—C11—C12—C131.0 (3)C15—C16—C20—O41.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg3 is the centroid of the N3/C11–C15 ring.
D—H···AD—HH···AD···AD—H···A
C7—H7···O10.942.202.808 (2)122
C4—H4···N20.942.412.760 (2)102
C14—H14···O40.942.162.808 (2)125
C17—H17···N30.942.402.752 (2)102
C22—H22C···Cg3i0.972.783.579 (2)140
Symmetry code: (i) x+1, y+1/2, z1/2.
 

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