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We report the design, synthesis, and crystal structure of a conjugated aryl­ene­ethynyl mol­ecule, 2-(2-{4,5-dimeth­oxy-2-[2-(2,3,4-tri­fluoro­phen­yl)ethyn­yl]phen­yl}ethyn­yl)-6-[2-(pyri­din-2-yl)ethyn­yl]pyri­dine, C30H17F3N2O2, that adopts a planar rhombus conformation in the solid state. The mol­ecule crystallizes in the space group P\overline{1}, with Z = 2, and features two intra­molecular sp2-C—H...N hydro­gen bonds that co-operatively hold the aryl­ethynyl mol­ecule in a rhombus conformation. The H atoms are activated towards hydro­gen bonding since they are situated on a tri­fluoro­phenyl ring and the H...N distances are 2.470 (16) and 2.646 (16) Å, with C—H...N angles of 161.7 (2) and 164.7 (2)°, respectively. Mol­ecular electrostatic potential calculations support the formation of C—H...N hydro­gen bonds to the tri­fluoro­phenyl moiety. Hirshfeld surface analysis identifies a self-com­plementary C—H...O dimeric inter­action between adjacent 1,2-di­meth­oxy­ben­zene segments that is shown to be common in structures containing that moiety.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621007427/ov3152sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229621007427/ov3152Isup2.hkl
Contains datablock I

cdx

Chemdraw file https://doi.org/10.1107/S2053229621007427/ov3152Isup3.cdx
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229621007427/ov3152Isup4.cml
Supplementary material

CCDC reference: 2097561

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: X-SEED (Barbour, 2020); software used to prepare material for publication: X-SEED (Barbour, 2020).

2-(2-{4,5-Dimethoxy-2-[2-(2,3,4-trifluorophenyl)ethynyl]phenyl}ethynyl)-6-[2-(pyridin-2-yl)ethynyl]pyridine top
Crystal data top
C30H17F3N2O2Z = 2
Mr = 494.45F(000) = 508
Triclinic, P1Dx = 1.428 Mg m3
a = 8.0037 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.1365 (6) ÅCell parameters from 4694 reflections
c = 13.4922 (6) Åθ = 2.7–27.1°
α = 104.697 (1)°µ = 0.11 mm1
β = 103.023 (1)°T = 100 K
γ = 106.619 (1)°Block, colorless
V = 1150.30 (10) Å30.56 × 0.23 × 0.21 mm
Data collection top
Bruker APEXI CCD
diffractometer
5017 independent reflections
Radiation source: fine-focus sealed tube3939 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
Detector resolution: 8.3660 pixels mm-1θmax = 27.2°, θmin = 1.7°
phi and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2014)
k = 1515
Tmin = 0.714, Tmax = 0.746l = 1717
14094 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: mixed
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0588P)2 + 0.8077P]
where P = (Fo2 + 2Fc2)/3
5017 reflections(Δ/σ)max < 0.001
342 parametersΔρmax = 0.62 e Å3
2 restraintsΔρmin = 0.28 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.

Refinement. A single crystal of (1) was mounted on a Kryoloop using viscous hydrocarbon oil. Data were collected using a Bruker Apex1 CCD diffractometer equipped with Mo Kα radiation with λ = 0.71073 Å. Data collection at low temperature was facilitated by use of a Kryoflex system with an accuracy of ±1 K. Initial data processing was carried out using the Apex II software suite (Bruker, 2014). Structures were solved using the dual-space method SHELXT-2018 (Sheldrick, 2015a) and refined against F2 using SHELXL-2018 (Sheldrick, 2015a). The program X-Seed was used as a graphical interface (Barbour, 2020).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.93690 (15)0.08813 (10)0.37066 (9)0.0311 (3)
O11.31660 (17)0.88155 (10)0.44776 (10)0.0240 (3)
N10.0723 (3)0.13168 (17)0.13171 (14)0.0378 (4)
C10.1550 (3)0.2497 (2)0.11907 (17)0.0425 (5)
H10.0825830.2899520.1497350.051*
F20.69008 (17)0.13974 (10)0.31484 (10)0.0363 (3)
O21.49544 (17)0.74849 (11)0.49921 (10)0.0250 (3)
N20.2829 (2)0.32816 (14)0.18746 (12)0.0252 (3)
C20.3375 (3)0.3149 (2)0.06455 (19)0.0468 (6)
H20.3909150.3975880.0595380.056*
F30.33172 (17)0.19383 (10)0.20777 (11)0.0415 (3)
C30.4429 (3)0.2590 (2)0.01701 (19)0.0517 (7)
H30.5696940.3031590.0226530.062*
C40.3609 (3)0.1355 (2)0.02768 (18)0.0433 (6)
H40.4303780.0946610.0045310.052*
C50.1755 (3)0.0755 (2)0.08671 (15)0.0318 (4)
C60.0797 (3)0.0525 (2)0.10419 (16)0.0314 (4)
C70.0030 (3)0.1584 (2)0.12007 (16)0.0315 (4)
C80.0992 (3)0.28441 (18)0.13770 (15)0.0287 (4)
C90.0065 (3)0.3576 (2)0.10534 (17)0.0357 (5)
H90.1225740.3234110.0691850.043*
C100.1020 (3)0.4785 (2)0.12585 (18)0.0386 (5)
H100.0392910.5290350.1056460.046*
C110.2900 (3)0.5265 (2)0.17605 (16)0.0316 (4)
H110.3599090.6099520.1908970.038*
C120.3745 (3)0.44607 (17)0.20460 (14)0.0248 (4)
C130.5703 (3)0.49169 (16)0.25491 (15)0.0247 (4)
C140.7342 (3)0.53331 (15)0.29700 (14)0.0229 (4)
C150.9293 (2)0.58423 (15)0.34847 (14)0.0208 (4)
C161.0247 (2)0.71038 (15)0.37281 (14)0.0211 (4)
H160.9583100.7601910.3553640.025*
C171.2128 (2)0.76185 (15)0.42156 (14)0.0204 (4)
C181.3113 (2)0.68818 (15)0.44922 (13)0.0203 (3)
C191.2188 (2)0.56456 (15)0.42579 (14)0.0203 (3)
H191.2855840.5153880.4443510.024*
C201.0280 (2)0.51129 (15)0.37507 (13)0.0200 (3)
C210.9300 (2)0.38337 (15)0.35011 (14)0.0212 (4)
C220.8351 (2)0.27841 (15)0.32648 (14)0.0213 (4)
C230.7068 (2)0.15664 (15)0.29617 (14)0.0211 (4)
C240.7605 (2)0.06497 (16)0.31951 (14)0.0224 (4)
C250.6342 (3)0.05248 (16)0.29105 (15)0.0268 (4)
C260.4526 (3)0.07785 (16)0.23721 (16)0.0291 (4)
C270.3928 (3)0.00974 (18)0.21204 (17)0.0311 (4)
H270.262 (2)0.024 (2)0.1754 (17)0.037*
C280.5200 (3)0.12693 (17)0.24219 (15)0.0258 (4)
H280.478 (3)0.1913 (17)0.2256 (17)0.031*
C291.2213 (3)0.95978 (16)0.42264 (16)0.0257 (4)
H29A1.1565400.9297300.3446440.039*
H29B1.3101781.0431710.4442200.039*
H29C1.1321470.9598550.4618970.039*
C301.6007 (3)0.68180 (17)0.53796 (16)0.0288 (4)
H30A1.5503890.6478550.5881650.043*
H30B1.7291760.7367520.5755210.043*
H30C1.5946640.6150850.4767430.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0262 (6)0.0265 (6)0.0392 (6)0.0096 (5)0.0059 (5)0.0127 (5)
O10.0253 (6)0.0133 (6)0.0321 (7)0.0059 (5)0.0059 (5)0.0099 (5)
N10.0381 (10)0.0376 (10)0.0318 (9)0.0048 (8)0.0098 (8)0.0136 (8)
C10.0477 (13)0.0429 (13)0.0286 (11)0.0050 (11)0.0127 (10)0.0113 (9)
F20.0454 (7)0.0206 (6)0.0502 (7)0.0155 (5)0.0194 (6)0.0161 (5)
O20.0241 (6)0.0157 (6)0.0330 (7)0.0061 (5)0.0049 (5)0.0100 (5)
N20.0243 (8)0.0321 (8)0.0230 (8)0.0117 (7)0.0105 (6)0.0113 (7)
C20.0442 (13)0.0459 (13)0.0365 (12)0.0008 (11)0.0220 (11)0.0034 (10)
F30.0377 (7)0.0186 (6)0.0579 (8)0.0012 (5)0.0197 (6)0.0054 (5)
C30.0231 (10)0.0602 (16)0.0393 (13)0.0034 (11)0.0093 (9)0.0140 (11)
C40.0262 (10)0.0588 (15)0.0310 (11)0.0089 (10)0.0087 (9)0.0006 (10)
C50.0251 (9)0.0409 (11)0.0235 (9)0.0031 (8)0.0121 (8)0.0078 (8)
C60.0245 (10)0.0405 (12)0.0269 (10)0.0081 (9)0.0108 (8)0.0099 (9)
C70.0254 (10)0.0443 (12)0.0264 (10)0.0123 (9)0.0106 (8)0.0127 (9)
C80.0284 (10)0.0362 (11)0.0245 (9)0.0120 (8)0.0124 (8)0.0114 (8)
C90.0268 (10)0.0575 (14)0.0339 (11)0.0236 (10)0.0121 (9)0.0220 (10)
C100.0435 (12)0.0529 (14)0.0395 (12)0.0337 (11)0.0181 (10)0.0259 (11)
C110.0346 (11)0.0410 (11)0.0290 (10)0.0199 (9)0.0150 (8)0.0166 (9)
C120.0266 (9)0.0320 (10)0.0203 (8)0.0135 (8)0.0110 (7)0.0098 (7)
C130.0302 (10)0.0209 (9)0.0255 (9)0.0105 (8)0.0099 (8)0.0100 (7)
C140.0305 (10)0.0161 (8)0.0245 (9)0.0083 (7)0.0111 (8)0.0088 (7)
C150.0258 (9)0.0169 (8)0.0194 (8)0.0063 (7)0.0087 (7)0.0063 (7)
C160.0262 (9)0.0167 (8)0.0234 (9)0.0090 (7)0.0092 (7)0.0092 (7)
C170.0273 (9)0.0117 (7)0.0212 (8)0.0045 (7)0.0093 (7)0.0058 (6)
C180.0236 (9)0.0177 (8)0.0199 (8)0.0066 (7)0.0078 (7)0.0069 (7)
C190.0269 (9)0.0155 (8)0.0216 (8)0.0096 (7)0.0092 (7)0.0081 (7)
C200.0278 (9)0.0148 (8)0.0180 (8)0.0066 (7)0.0095 (7)0.0059 (6)
C210.0254 (9)0.0191 (8)0.0215 (8)0.0086 (7)0.0100 (7)0.0080 (7)
C220.0248 (9)0.0188 (8)0.0215 (8)0.0082 (7)0.0089 (7)0.0070 (7)
C230.0257 (9)0.0169 (8)0.0201 (8)0.0056 (7)0.0109 (7)0.0049 (7)
C240.0239 (9)0.0200 (8)0.0233 (9)0.0068 (7)0.0100 (7)0.0063 (7)
C250.0391 (11)0.0165 (8)0.0302 (10)0.0125 (8)0.0171 (8)0.0086 (7)
C260.0276 (10)0.0182 (9)0.0333 (10)0.0014 (7)0.0150 (8)0.0021 (8)
C270.0235 (9)0.0271 (10)0.0358 (11)0.0036 (8)0.0105 (8)0.0050 (8)
C280.0268 (9)0.0221 (9)0.0284 (9)0.0079 (8)0.0119 (8)0.0071 (7)
C290.0293 (9)0.0157 (8)0.0343 (10)0.0089 (7)0.0087 (8)0.0125 (7)
C300.0272 (10)0.0231 (9)0.0351 (10)0.0103 (8)0.0038 (8)0.0126 (8)
Geometric parameters (Å, º) top
F1—C241.336 (2)C12—C131.434 (3)
O1—C171.3573 (19)C13—C141.199 (3)
O1—C291.435 (2)C14—C151.430 (3)
N1—C11.342 (3)C15—C201.404 (2)
N1—C51.350 (3)C15—C161.413 (2)
C1—C21.364 (3)C16—C171.377 (2)
C1—H10.9500C16—H160.9500
F2—C251.343 (2)C17—C181.415 (2)
O2—C181.359 (2)C18—C191.385 (2)
O2—C301.430 (2)C19—C201.399 (2)
N2—C121.340 (2)C19—H190.9500
N2—C81.350 (2)C20—C211.435 (2)
C2—C31.374 (4)C21—C221.197 (2)
C2—H20.9500C22—C231.429 (2)
F3—C261.356 (2)C23—C241.383 (2)
C3—C41.408 (4)C23—C281.401 (3)
C3—H30.9500C24—C251.387 (2)
C4—C51.386 (3)C25—C261.375 (3)
C4—H40.9500C26—C271.369 (3)
C5—C61.452 (3)C27—C281.384 (3)
C6—C71.202 (3)C27—H270.966 (16)
C7—C81.431 (3)C28—H280.991 (15)
C8—C91.400 (3)C29—H29A0.9800
C9—C101.367 (3)C29—H29B0.9800
C9—H90.9500C29—H29C0.9800
C10—C111.378 (3)C30—H30A0.9800
C10—H100.9500C30—H30B0.9800
C11—C121.417 (3)C30—H30C0.9800
C11—H110.9500
C17—O1—C29116.89 (14)O1—C17—C16125.12 (15)
C1—N1—C5117.94 (19)O1—C17—C18115.18 (15)
N1—C1—C2123.5 (2)C16—C17—C18119.70 (15)
N1—C1—H1118.3O2—C18—C19125.11 (15)
C2—C1—H1118.3O2—C18—C17114.96 (14)
C18—O2—C30117.80 (13)C19—C18—C17119.92 (16)
C12—N2—C8116.88 (16)C18—C19—C20120.71 (16)
C1—C2—C3118.9 (2)C18—C19—H19119.6
C1—C2—H2120.5C20—C19—H19119.6
C3—C2—H2120.5C19—C20—C15119.59 (15)
C2—C3—C4119.3 (2)C19—C20—C21121.44 (15)
C2—C3—H3120.4C15—C20—C21118.97 (16)
C4—C3—H3120.4C22—C21—C20174.56 (19)
C5—C4—C3117.9 (2)C21—C22—C23174.48 (19)
C5—C4—H4121.1C24—C23—C28117.76 (16)
C3—C4—H4121.1C24—C23—C22121.90 (16)
N1—C5—C4122.4 (2)C28—C23—C22120.33 (16)
N1—C5—C6115.63 (17)F1—C24—C23120.29 (15)
C4—C5—C6121.9 (2)F1—C24—C25118.35 (16)
C7—C6—C5178.6 (2)C23—C24—C25121.35 (17)
C6—C7—C8179.1 (2)F2—C25—C26120.96 (16)
N2—C8—C9122.28 (18)F2—C25—C24120.12 (18)
N2—C8—C7116.30 (17)C26—C25—C24118.91 (17)
C9—C8—C7121.42 (18)F3—C26—C27119.98 (18)
C10—C9—C8119.89 (19)F3—C26—C25118.14 (17)
C10—C9—H9120.1C27—C26—C25121.88 (17)
C8—C9—H9120.1C26—C27—C28118.57 (19)
C9—C10—C11119.56 (19)C26—C27—H27110.7 (14)
C9—C10—H10120.2C28—C27—H27130.7 (14)
C11—C10—H10120.2C27—C28—C23121.51 (18)
C10—C11—C12117.26 (19)C27—C28—H28119.1 (13)
C10—C11—H11121.4C23—C28—H28119.4 (13)
C12—C11—H11121.4O1—C29—H29A109.5
N2—C12—C11124.10 (17)O1—C29—H29B109.5
N2—C12—C13116.87 (16)H29A—C29—H29B109.5
C11—C12—C13119.04 (17)O1—C29—H29C109.5
C14—C13—C12178.00 (18)H29A—C29—H29C109.5
C13—C14—C15179.1 (2)H29B—C29—H29C109.5
C20—C15—C16119.37 (16)O2—C30—H30A109.5
C20—C15—C14121.26 (15)O2—C30—H30B109.5
C16—C15—C14119.37 (15)H30A—C30—H30B109.5
C17—C16—C15120.70 (16)O2—C30—H30C109.5
C17—C16—H16119.6H30A—C30—H30C109.5
C15—C16—H16119.6H30B—C30—H30C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11···F3i0.952.413.220 (2)143
C27—H27···N10.97 (2)2.47 (2)3.400 (3)162 (2)
C28—H28···N20.99 (2)2.65 (2)3.612 (2)165 (2)
C29—H29B···O2ii0.982.373.350 (2)175
Symmetry codes: (i) x, y+1, z; (ii) x+3, y+2, z+1.
 

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