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In the cation of the title compound, C15H16NO+·C24H20B-, the pyridyl ring makes a dihedral angle of 14.03° with the phenyl ring. The anion has a slightly distorted tetrahedral geometry and forms honeycomb-like sheets which extend along the b axis, forming channels containing the cations. A comparison of packing energies reveals a difference between the title compound and a similar material which has non-linear optical properties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100007538/da1127sup1.cif
Contains datablocks I, y755

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100007538/da1127Isup2.hkl
Contains datablock I

CCDC reference: 150843

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

4-[2-(4-methoxyphenyl)ethenyl]-N-methylpyridinum tetraphenylborate top
Crystal data top
C15H16NO+·C24H20BDx = 1.202 Mg m3
Mr = 545.50Melting point = 509–510 K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.029 (2) ÅCell parameters from 26 reflections
b = 10.819 (2) Åθ = 3.8–17.2°
c = 21.660 (3) ŵ = 0.07 mm1
β = 99.16 (1)°T = 296 K
V = 3014.3 (8) Å3Granular, yellow-green
Z = 40.60 × 0.56 × 0.52 mm
F(000) = 1160
Data collection top
Siemens P4
diffractometer
Rint = 0.010
Radiation source: normal-focus sealed tubeθmax = 25.0°, θmin = 1.6°
Graphite monochromatorh = 015
ω scansk = 112
6502 measured reflectionsl = 2525
5318 independent reflections3 standard reflections every 97 reflections
3204 reflections with I > 2σ(I) intensity decay: 2.7%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.047P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.87(Δ/σ)max < 0.001
5318 reflectionsΔρmax = 0.13 e Å3
382 parametersΔρmin = 0.11 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001Fc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0103 (7)
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.

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
xyzUiso*/Ueq
O0.10266 (9)0.19999 (12)0.53477 (6)0.0769 (4)
N0.29052 (10)0.74021 (13)0.65390 (6)0.0595 (4)
B0.69076 (13)0.64864 (16)0.65696 (7)0.0442 (4)
C10.33552 (16)0.86130 (17)0.67301 (8)0.0823 (6)
H1A0.34870.90590.63680.099*
H1B0.28770.90720.69360.099*
H1C0.39950.85000.70120.099*
C20.22191 (14)0.68803 (17)0.68588 (8)0.0672 (5)
H20.19960.73140.71840.081*
C30.18459 (13)0.57303 (18)0.67152 (8)0.0665 (5)
H30.13690.53880.69430.080*
C40.21622 (12)0.50480 (16)0.62314 (7)0.0541 (4)
C50.28438 (12)0.56409 (16)0.58945 (7)0.0597 (4)
H50.30530.52460.55540.072*
C60.32044 (13)0.67866 (17)0.60586 (7)0.0638 (5)
H60.36720.71580.58330.077*
C70.18011 (13)0.37902 (17)0.61133 (7)0.0614 (5)
H70.12620.35290.63160.074*
C80.21639 (12)0.29757 (16)0.57449 (7)0.0590 (4)
H80.26720.32560.55220.071*
C90.18524 (12)0.16908 (16)0.56520 (7)0.0552 (4)
C100.10596 (13)0.11727 (17)0.59262 (8)0.0674 (5)
H100.07180.16640.61820.081*
C110.07637 (14)0.00368 (17)0.58330 (8)0.0665 (5)
H110.02280.03540.60230.080*
C120.12592 (13)0.07825 (17)0.54584 (7)0.0591 (4)
C130.20576 (13)0.02960 (18)0.51816 (8)0.0679 (5)
H130.24000.07950.49300.082*
C140.23460 (13)0.09173 (18)0.52766 (7)0.0645 (5)
H140.28820.12300.50860.077*
C150.01622 (14)0.25046 (17)0.55875 (9)0.0774 (5)
H15A0.04530.20440.54280.093*
H15B0.00690.33530.54600.093*
H15C0.02870.24580.60360.093*
C160.61630 (11)0.63389 (13)0.71136 (6)0.0420 (3)
C170.63123 (12)0.69754 (14)0.76809 (7)0.0549 (4)
H170.68900.74870.77730.066*
C180.56405 (14)0.68797 (16)0.81118 (8)0.0655 (5)
H180.57670.73350.84800.079*
C190.47916 (13)0.61218 (16)0.80010 (8)0.0632 (5)
H190.43430.60540.82930.076*
C200.46104 (12)0.54604 (15)0.74514 (7)0.0581 (4)
H200.40420.49320.73720.070*
C210.52774 (11)0.55848 (14)0.70190 (7)0.0497 (4)
H210.51310.51460.66460.060*
C220.74043 (11)0.51675 (14)0.63833 (6)0.0460 (4)
C230.71699 (12)0.39954 (14)0.65789 (7)0.0527 (4)
H230.66770.39200.68430.063*
C240.76355 (14)0.29307 (15)0.63989 (8)0.0642 (5)
H240.74520.21670.65450.077*
C250.83580 (14)0.29923 (18)0.60106 (8)0.0693 (5)
H250.86710.22780.58900.083*
C260.86168 (14)0.41300 (19)0.58002 (8)0.0759 (5)
H260.91080.41900.55330.091*
C270.81494 (13)0.51884 (16)0.59837 (8)0.0660 (5)
H270.83390.59470.58350.079*
C280.61428 (11)0.70558 (13)0.59592 (6)0.0441 (4)
C290.58404 (12)0.64129 (14)0.54018 (6)0.0523 (4)
H290.61130.56280.53620.063*
C300.51534 (13)0.68871 (17)0.49038 (7)0.0626 (5)
H300.49680.64170.45440.075*
C310.47465 (13)0.80478 (18)0.49410 (8)0.0653 (5)
H310.42970.83780.46050.078*
C320.50112 (12)0.87181 (15)0.54827 (8)0.0593 (4)
H320.47400.95060.55150.071*
C330.56820 (11)0.82186 (14)0.59802 (7)0.0503 (4)
H330.58330.86790.63460.060*
C340.79047 (11)0.73873 (14)0.68235 (7)0.0460 (4)
C350.80708 (12)0.85890 (15)0.66266 (7)0.0547 (4)
H350.75820.89400.63160.066*
C360.89368 (15)0.92842 (17)0.68753 (9)0.0668 (5)
H360.90051.00900.67380.080*
C370.96907 (14)0.87920 (19)0.73217 (9)0.0705 (5)
H371.02740.92520.74850.085*
C380.95669 (13)0.76085 (18)0.75218 (8)0.0663 (5)
H381.00740.72540.78200.080*
C390.86929 (12)0.69418 (15)0.72819 (7)0.0578 (4)
H390.86240.61480.74350.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O0.0729 (8)0.0727 (9)0.0892 (9)0.0025 (7)0.0258 (7)0.0152 (7)
N0.0592 (9)0.0726 (10)0.0466 (8)0.0076 (8)0.0077 (7)0.0002 (7)
B0.0484 (10)0.0422 (10)0.0430 (9)0.0007 (8)0.0101 (8)0.0015 (8)
C10.0983 (15)0.0854 (15)0.0637 (11)0.0269 (12)0.0145 (11)0.0150 (10)
C20.0722 (12)0.0813 (14)0.0514 (10)0.0039 (11)0.0201 (9)0.0045 (10)
C30.0659 (12)0.0800 (13)0.0590 (11)0.0078 (10)0.0265 (9)0.0017 (10)
C40.0501 (10)0.0646 (11)0.0479 (9)0.0012 (9)0.0085 (8)0.0067 (8)
C50.0613 (11)0.0704 (12)0.0500 (9)0.0059 (10)0.0168 (8)0.0017 (9)
C60.0652 (11)0.0808 (13)0.0486 (10)0.0114 (10)0.0186 (8)0.0014 (9)
C70.0560 (10)0.0738 (13)0.0575 (10)0.0026 (10)0.0186 (9)0.0064 (9)
C80.0515 (10)0.0763 (12)0.0501 (9)0.0017 (9)0.0103 (8)0.0078 (9)
C90.0492 (9)0.0711 (12)0.0460 (9)0.0001 (9)0.0097 (7)0.0022 (8)
C100.0704 (12)0.0703 (13)0.0674 (11)0.0024 (10)0.0293 (10)0.0073 (9)
C110.0636 (11)0.0751 (13)0.0668 (11)0.0019 (10)0.0290 (9)0.0036 (10)
C120.0542 (10)0.0687 (12)0.0541 (10)0.0034 (9)0.0071 (8)0.0046 (9)
C130.0549 (11)0.0853 (14)0.0676 (11)0.0020 (10)0.0221 (9)0.0159 (10)
C140.0508 (10)0.0870 (14)0.0587 (10)0.0036 (10)0.0186 (8)0.0055 (10)
C150.0711 (13)0.0777 (13)0.0830 (13)0.0075 (11)0.0114 (11)0.0008 (10)
C160.0449 (8)0.0392 (8)0.0413 (8)0.0059 (7)0.0054 (6)0.0033 (7)
C170.0581 (10)0.0591 (10)0.0491 (9)0.0033 (9)0.0137 (8)0.0072 (8)
C180.0745 (12)0.0751 (12)0.0511 (9)0.0029 (11)0.0220 (9)0.0107 (9)
C190.0604 (11)0.0764 (12)0.0585 (11)0.0127 (10)0.0264 (9)0.0143 (10)
C200.0492 (10)0.0617 (11)0.0643 (11)0.0005 (9)0.0120 (8)0.0120 (9)
C210.0516 (9)0.0511 (10)0.0466 (9)0.0035 (8)0.0080 (7)0.0015 (7)
C220.0482 (9)0.0490 (10)0.0410 (8)0.0010 (8)0.0073 (7)0.0015 (7)
C230.0603 (10)0.0503 (10)0.0489 (9)0.0081 (9)0.0131 (8)0.0009 (8)
C240.0769 (12)0.0496 (10)0.0650 (11)0.0081 (9)0.0078 (10)0.0031 (9)
C250.0707 (12)0.0657 (13)0.0700 (12)0.0163 (10)0.0072 (10)0.0185 (10)
C260.0701 (12)0.0855 (15)0.0788 (13)0.0094 (11)0.0323 (10)0.0165 (11)
C270.0709 (12)0.0576 (11)0.0762 (12)0.0005 (9)0.0319 (10)0.0046 (9)
C280.0492 (9)0.0438 (9)0.0417 (8)0.0051 (7)0.0146 (7)0.0017 (7)
C290.0625 (10)0.0528 (10)0.0430 (9)0.0039 (8)0.0131 (8)0.0007 (8)
C300.0687 (11)0.0770 (13)0.0419 (9)0.0161 (10)0.0084 (8)0.0043 (9)
C310.0595 (11)0.0835 (14)0.0515 (10)0.0049 (10)0.0050 (8)0.0246 (10)
C320.0587 (10)0.0583 (11)0.0626 (10)0.0052 (9)0.0150 (9)0.0194 (9)
C330.0552 (10)0.0494 (10)0.0476 (9)0.0014 (8)0.0122 (7)0.0028 (8)
C340.0489 (9)0.0486 (10)0.0429 (8)0.0025 (8)0.0149 (7)0.0017 (7)
C350.0592 (10)0.0519 (10)0.0558 (10)0.0029 (9)0.0182 (8)0.0030 (8)
C360.0723 (13)0.0571 (11)0.0774 (12)0.0146 (10)0.0319 (11)0.0105 (10)
C370.0593 (12)0.0825 (15)0.0741 (12)0.0226 (11)0.0240 (10)0.0258 (11)
C380.0506 (10)0.0881 (14)0.0600 (11)0.0029 (10)0.0083 (9)0.0084 (10)
C390.0540 (10)0.0599 (11)0.0602 (10)0.0031 (9)0.0108 (8)0.0005 (9)
Geometric parameters (Å, º) top
O—C121.3642 (19)C16—C211.4014 (19)
O—C151.4221 (19)C17—C181.381 (2)
N—C21.340 (2)C18—C191.367 (2)
N—C61.3443 (19)C19—C201.377 (2)
N—C11.468 (2)C20—C211.382 (2)
B—C221.643 (2)C22—C231.386 (2)
B—C281.643 (2)C22—C271.400 (2)
B—C341.647 (2)C23—C241.386 (2)
B—C161.649 (2)C24—C251.360 (2)
C2—C31.354 (2)C25—C261.373 (2)
C3—C41.397 (2)C26—C271.385 (2)
C4—C51.392 (2)C28—C291.3946 (19)
C4—C71.449 (2)C28—C331.398 (2)
C5—C61.353 (2)C29—C301.386 (2)
C7—C81.325 (2)C30—C311.370 (2)
C8—C91.453 (2)C31—C321.376 (2)
C9—C101.389 (2)C32—C331.385 (2)
C9—C141.393 (2)C34—C391.396 (2)
C10—C111.370 (2)C34—C351.396 (2)
C11—C121.376 (2)C35—C361.391 (2)
C12—C131.385 (2)C36—C371.371 (2)
C13—C141.372 (2)C37—C381.370 (2)
C16—C171.3950 (19)C38—C391.378 (2)
C12—O—C15118.24 (14)C21—C16—B121.08 (12)
C2—N—C6119.41 (15)C18—C17—C16122.94 (15)
C2—N—C1119.98 (15)C19—C18—C17120.55 (15)
C6—N—C1120.56 (14)C18—C19—C20119.09 (15)
C22—B—C28109.87 (12)C19—C20—C21119.71 (15)
C22—B—C34105.98 (12)C20—C21—C16123.34 (14)
C28—B—C34113.07 (12)C23—C22—C27114.32 (14)
C22—B—C16113.01 (12)C23—C22—B127.21 (13)
C28—B—C16105.12 (11)C27—C22—B118.47 (14)
C34—B—C16109.94 (11)C22—C23—C24123.13 (15)
N—C2—C3120.88 (16)C25—C24—C23120.67 (17)
C2—C3—C4121.34 (16)C24—C25—C26118.68 (17)
C5—C4—C3116.02 (16)C25—C26—C27120.24 (16)
C5—C4—C7123.80 (15)C26—C27—C22122.97 (16)
C3—C4—C7120.16 (15)C29—C28—C33114.42 (14)
C6—C5—C4120.54 (15)C29—C28—B124.13 (13)
N—C6—C5121.72 (15)C33—C28—B121.31 (13)
C8—C7—C4126.42 (16)C30—C29—C28123.21 (15)
C7—C8—C9126.94 (15)C31—C30—C29120.09 (16)
C10—C9—C14116.80 (17)C30—C31—C32119.11 (16)
C10—C9—C8122.48 (15)C31—C32—C33119.97 (16)
C14—C9—C8120.71 (15)C32—C33—C28123.17 (15)
C11—C10—C9122.23 (16)C39—C34—C35114.00 (14)
C10—C11—C12119.97 (16)C39—C34—B119.02 (13)
O—C12—C11123.91 (16)C35—C34—B126.98 (14)
O—C12—C13116.88 (16)C36—C35—C34122.74 (16)
C11—C12—C13119.20 (17)C37—C36—C35120.59 (17)
C14—C13—C12120.37 (16)C38—C37—C36118.61 (17)
C13—C14—C9121.42 (16)C37—C38—C39120.13 (18)
C17—C16—C21114.35 (13)C38—C39—C34123.90 (16)
C17—C16—B124.50 (13)
C6—N—C2—C31.8 (2)C34—B—C22—C23128.17 (15)
C1—N—C2—C3175.73 (16)C16—B—C22—C237.7 (2)
N—C2—C3—C40.1 (3)C28—B—C22—C2770.63 (17)
C2—C3—C4—C52.6 (2)C34—B—C22—C2751.85 (17)
C2—C3—C4—C7176.09 (16)C16—B—C22—C27172.32 (13)
C3—C4—C5—C63.2 (2)C27—C22—C23—C240.4 (2)
C7—C4—C5—C6175.39 (16)B—C22—C23—C24179.64 (15)
C2—N—C6—C51.1 (2)C22—C23—C24—C250.3 (3)
C1—N—C6—C5176.38 (16)C23—C24—C25—C260.0 (3)
C4—C5—C6—N1.5 (2)C24—C25—C26—C270.2 (3)
C5—C4—C7—C810.4 (3)C25—C26—C27—C220.1 (3)
C3—C4—C7—C8168.18 (16)C23—C22—C27—C260.2 (2)
C4—C7—C8—C9175.97 (15)B—C22—C27—C26179.80 (16)
C7—C8—C9—C103.9 (3)C22—B—C28—C299.31 (19)
C7—C8—C9—C14176.17 (16)C34—B—C28—C29127.49 (15)
C14—C9—C10—C110.4 (2)C16—B—C28—C29112.57 (15)
C8—C9—C10—C11179.47 (16)C22—B—C28—C33175.26 (12)
C9—C10—C11—C120.2 (3)C34—B—C28—C3357.09 (17)
C15—O—C12—C115.8 (2)C16—B—C28—C3362.85 (16)
C15—O—C12—C13175.51 (14)C33—C28—C29—C301.0 (2)
C10—C11—C12—O178.95 (16)B—C28—C29—C30176.67 (13)
C10—C11—C12—C130.3 (3)C28—C29—C30—C310.9 (2)
O—C12—C13—C14179.23 (15)C29—C30—C31—C321.5 (2)
C11—C12—C13—C140.4 (3)C30—C31—C32—C330.1 (2)
C12—C13—C14—C90.2 (3)C31—C32—C33—C281.9 (2)
C10—C9—C14—C130.2 (2)C29—C28—C33—C322.4 (2)
C8—C9—C14—C13179.66 (15)B—C28—C33—C32178.20 (13)
C22—B—C16—C17123.47 (15)C22—B—C34—C3950.68 (16)
C28—B—C16—C17116.71 (15)C28—B—C34—C39171.10 (13)
C34—B—C16—C175.28 (19)C16—B—C34—C3971.76 (16)
C22—B—C16—C2159.85 (17)C22—B—C34—C35128.85 (14)
C28—B—C16—C2159.97 (17)C28—B—C34—C358.4 (2)
C34—B—C16—C21178.03 (13)C16—B—C34—C35108.71 (16)
C21—C16—C17—C180.5 (2)C39—C34—C35—C361.1 (2)
B—C16—C17—C18176.39 (15)B—C34—C35—C36179.30 (14)
C16—C17—C18—C191.2 (3)C34—C35—C36—C371.8 (2)
C17—C18—C19—C200.4 (3)C35—C36—C37—C380.7 (2)
C18—C19—C20—C210.9 (2)C36—C37—C38—C390.8 (2)
C19—C20—C21—C161.6 (2)C37—C38—C39—C341.5 (2)
C17—C16—C21—C200.9 (2)C35—C34—C39—C380.5 (2)
B—C16—C21—C20177.89 (13)B—C34—C39—C38179.12 (14)
C28—B—C22—C23109.35 (16)
Ion packing energies (PE) (kJ mol-1) top
InteractionPE
anion···anioni-12.1
anion···anionii-10.0
anion···anioniii-10.0
anion···anioniv-7.1
anion···anionv-7.1
cation···cationvi-15.3
cation···cationvii-12.6
cation···cationviii-12.6
anion···cationi-23.6
anion···cationii-25.7
anion···cationiii-25.7
anion···cationvii-6.9
anion···cationviii-6.9
anion···cationvi-0.2
Symmetry codes: (i) 1 - x, -y - 1, 1 - z; (ii) 1 - x, y - 1/2, 3/2 - z; (iii) 1 - x, y + 1/2, 3/2 - z; (iv) 2 - x, y - 1/2, 3/2 - z; (v) 2 - x, y + 1/2, 3/2 - z; (vi) -x, -y, 1 - z; (vii) x, y - 1, z; (viii) x, y + 1, z.
 

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