4-[2-(4-Methoxyphenyl)ethenyl]-N-methylpyridinium tetraphenylborate

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.

Computing details

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

Crystal data

C15H16NO^+·C24H20B^−	Dx = 1.202 Mg m^−3
Mr = 545.50	Melting point = 509–510 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.029 (2) Å	Cell parameters from 26 reflections
b = 10.819 (2) Å	θ = 3.8–17.2°
c = 21.660 (3) Å	µ = 0.07 mm^−1
β = 99.16 (1)°	T = 296 K
V = 3014.3 (8) Å^3	Granular, yellow-green
Z = 4	0.60 × 0.56 × 0.52 mm
F(000) = 1160

Data collection

Siemens P4 diffractometer	Rint = 0.010
Radiation source: normal-focus sealed tube	θmax = 25.0°, θmin = 1.6°
Graphite monochromator	h = 0→15
ω scans	k = −1→12
6502 measured reflections	l = −25→25
5318 independent reflections	3 standard reflections every 97 reflections
3204 reflections with I > 2σ(I)	intensity decay: 2.7%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.047P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.87	(Δ/σ)max < 0.001
5318 reflections	Δρmax = 0.13 e Å^−3
382 parameters	Δρmin = −0.11 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001Fc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0103 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O	0.10266 (9)	0.19999 (12)	0.53477 (6)	0.0769 (4)
N	0.29052 (10)	−0.74021 (13)	0.65390 (6)	0.0595 (4)
B	0.69076 (13)	−0.64864 (16)	0.65696 (7)	0.0442 (4)
C1	0.33552 (16)	−0.86130 (17)	0.67301 (8)	0.0823 (6)
H1A	0.3487	−0.9059	0.6368	0.099*
H1B	0.2877	−0.9072	0.6936	0.099*
H1C	0.3995	−0.8500	0.7012	0.099*
C2	0.22191 (14)	−0.68803 (17)	0.68588 (8)	0.0672 (5)
H2	0.1996	−0.7314	0.7184	0.081*
C3	0.18459 (13)	−0.57303 (18)	0.67152 (8)	0.0665 (5)
H3	0.1369	−0.5388	0.6943	0.080*
C4	0.21622 (12)	−0.50480 (16)	0.62314 (7)	0.0541 (4)
C5	0.28438 (12)	−0.56409 (16)	0.58945 (7)	0.0597 (4)
H5	0.3053	−0.5246	0.5554	0.072*
C6	0.32044 (13)	−0.67866 (17)	0.60586 (7)	0.0638 (5)
H6	0.3672	−0.7158	0.5833	0.077*
C7	0.18011 (13)	−0.37902 (17)	0.61133 (7)	0.0614 (5)
H7	0.1262	−0.3529	0.6316	0.074*
C8	0.21639 (12)	−0.29757 (16)	0.57449 (7)	0.0590 (4)
H8	0.2672	−0.3256	0.5522	0.071*
C9	0.18524 (12)	−0.16908 (16)	0.56520 (7)	0.0552 (4)
C10	0.10596 (13)	−0.11727 (17)	0.59262 (8)	0.0674 (5)
H10	0.0718	−0.1664	0.6182	0.081*
C11	0.07637 (14)	0.00368 (17)	0.58330 (8)	0.0665 (5)
H11	0.0228	0.0354	0.6023	0.080*
C12	0.12592 (13)	0.07825 (17)	0.54584 (7)	0.0591 (4)
C13	0.20576 (13)	0.02960 (18)	0.51816 (8)	0.0679 (5)
H13	0.2400	0.0795	0.4930	0.082*
C14	0.23460 (13)	−0.09173 (18)	0.52766 (7)	0.0645 (5)
H14	0.2882	−0.1230	0.5086	0.077*
C15	0.01622 (14)	0.25046 (17)	0.55875 (9)	0.0774 (5)
H15A	−0.0453	0.2044	0.5428	0.093*
H15B	0.0069	0.3353	0.5460	0.093*
H15C	0.0287	0.2458	0.6036	0.093*
C16	0.61630 (11)	−0.63389 (13)	0.71136 (6)	0.0420 (3)
C17	0.63123 (12)	−0.69754 (14)	0.76809 (7)	0.0549 (4)
H17	0.6890	−0.7487	0.7773	0.066*
C18	0.56405 (14)	−0.68797 (16)	0.81118 (8)	0.0655 (5)
H18	0.5767	−0.7335	0.8480	0.079*
C19	0.47916 (13)	−0.61218 (16)	0.80010 (8)	0.0632 (5)
H19	0.4343	−0.6054	0.8293	0.076*
C20	0.46104 (12)	−0.54604 (15)	0.74514 (7)	0.0581 (4)
H20	0.4042	−0.4932	0.7372	0.070*
C21	0.52774 (11)	−0.55848 (14)	0.70190 (7)	0.0497 (4)
H21	0.5131	−0.5146	0.6646	0.060*
C22	0.74043 (11)	−0.51675 (14)	0.63833 (6)	0.0460 (4)
C23	0.71699 (12)	−0.39954 (14)	0.65789 (7)	0.0527 (4)
H23	0.6677	−0.3920	0.6843	0.063*
C24	0.76355 (14)	−0.29307 (15)	0.63989 (8)	0.0642 (5)
H24	0.7452	−0.2167	0.6545	0.077*
C25	0.83580 (14)	−0.29923 (18)	0.60106 (8)	0.0693 (5)
H25	0.8671	−0.2278	0.5890	0.083*
C26	0.86168 (14)	−0.41300 (19)	0.58002 (8)	0.0759 (5)
H26	0.9108	−0.4190	0.5533	0.091*
C27	0.81494 (13)	−0.51884 (16)	0.59837 (8)	0.0660 (5)
H27	0.8339	−0.5947	0.5835	0.079*
C28	0.61428 (11)	−0.70558 (13)	0.59592 (6)	0.0441 (4)
C29	0.58404 (12)	−0.64129 (14)	0.54018 (6)	0.0523 (4)
H29	0.6113	−0.5628	0.5362	0.063*
C30	0.51534 (13)	−0.68871 (17)	0.49038 (7)	0.0626 (5)
H30	0.4968	−0.6417	0.4544	0.075*
C31	0.47465 (13)	−0.80478 (18)	0.49410 (8)	0.0653 (5)
H31	0.4297	−0.8378	0.4605	0.078*
C32	0.50112 (12)	−0.87181 (15)	0.54827 (8)	0.0593 (4)
H32	0.4740	−0.9506	0.5515	0.071*
C33	0.56820 (11)	−0.82186 (14)	0.59802 (7)	0.0503 (4)
H33	0.5833	−0.8679	0.6346	0.060*
C34	0.79047 (11)	−0.73873 (14)	0.68235 (7)	0.0460 (4)
C35	0.80708 (12)	−0.85890 (15)	0.66266 (7)	0.0547 (4)
H35	0.7582	−0.8940	0.6316	0.066*
C36	0.89368 (15)	−0.92842 (17)	0.68753 (9)	0.0668 (5)
H36	0.9005	−1.0090	0.6738	0.080*
C37	0.96907 (14)	−0.87920 (19)	0.73217 (9)	0.0705 (5)
H37	1.0274	−0.9252	0.7485	0.085*
C38	0.95669 (13)	−0.76085 (18)	0.75218 (8)	0.0663 (5)
H38	1.0074	−0.7254	0.7820	0.080*
C39	0.86929 (12)	−0.69418 (15)	0.72819 (7)	0.0578 (4)
H39	0.8624	−0.6148	0.7435	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O	0.0729 (8)	0.0727 (9)	0.0892 (9)	0.0025 (7)	0.0258 (7)	0.0152 (7)
N	0.0592 (9)	0.0726 (10)	0.0466 (8)	0.0076 (8)	0.0077 (7)	−0.0002 (7)
B	0.0484 (10)	0.0422 (10)	0.0430 (9)	0.0007 (8)	0.0101 (8)	0.0015 (8)
C1	0.0983 (15)	0.0854 (15)	0.0637 (11)	0.0269 (12)	0.0145 (11)	0.0150 (10)
C2	0.0722 (12)	0.0813 (14)	0.0514 (10)	0.0039 (11)	0.0201 (9)	0.0045 (10)
C3	0.0659 (12)	0.0800 (13)	0.0590 (11)	0.0078 (10)	0.0265 (9)	−0.0017 (10)
C4	0.0501 (10)	0.0646 (11)	0.0479 (9)	0.0012 (9)	0.0085 (8)	−0.0067 (8)
C5	0.0613 (11)	0.0704 (12)	0.0500 (9)	0.0059 (10)	0.0168 (8)	0.0017 (9)
C6	0.0652 (11)	0.0808 (13)	0.0486 (10)	0.0114 (10)	0.0186 (8)	−0.0014 (9)
C7	0.0560 (10)	0.0738 (13)	0.0575 (10)	0.0026 (10)	0.0186 (9)	−0.0064 (9)
C8	0.0515 (10)	0.0763 (12)	0.0501 (9)	0.0017 (9)	0.0103 (8)	−0.0078 (9)
C9	0.0492 (9)	0.0711 (12)	0.0460 (9)	0.0001 (9)	0.0097 (7)	−0.0022 (8)
C10	0.0704 (12)	0.0703 (13)	0.0674 (11)	−0.0024 (10)	0.0293 (10)	0.0073 (9)
C11	0.0636 (11)	0.0751 (13)	0.0668 (11)	0.0019 (10)	0.0290 (9)	0.0036 (10)
C12	0.0542 (10)	0.0687 (12)	0.0541 (10)	−0.0034 (9)	0.0071 (8)	0.0046 (9)
C13	0.0549 (11)	0.0853 (14)	0.0676 (11)	−0.0020 (10)	0.0221 (9)	0.0159 (10)
C14	0.0508 (10)	0.0870 (14)	0.0587 (10)	0.0036 (10)	0.0186 (8)	0.0055 (10)
C15	0.0711 (13)	0.0777 (13)	0.0830 (13)	0.0075 (11)	0.0114 (11)	0.0008 (10)
C16	0.0449 (8)	0.0392 (8)	0.0413 (8)	−0.0059 (7)	0.0054 (6)	−0.0033 (7)
C17	0.0581 (10)	0.0591 (10)	0.0491 (9)	0.0033 (9)	0.0137 (8)	0.0072 (8)
C18	0.0745 (12)	0.0751 (12)	0.0511 (9)	−0.0029 (11)	0.0220 (9)	0.0107 (9)
C19	0.0604 (11)	0.0764 (12)	0.0585 (11)	−0.0127 (10)	0.0264 (9)	−0.0143 (10)
C20	0.0492 (10)	0.0617 (11)	0.0643 (11)	−0.0005 (9)	0.0120 (8)	−0.0120 (9)
C21	0.0516 (9)	0.0511 (10)	0.0466 (9)	−0.0035 (8)	0.0080 (7)	−0.0015 (7)
C22	0.0482 (9)	0.0490 (10)	0.0410 (8)	−0.0010 (8)	0.0073 (7)	0.0015 (7)
C23	0.0603 (10)	0.0503 (10)	0.0489 (9)	−0.0081 (9)	0.0131 (8)	−0.0009 (8)
C24	0.0769 (12)	0.0496 (10)	0.0650 (11)	−0.0081 (9)	0.0078 (10)	0.0031 (9)
C25	0.0707 (12)	0.0657 (13)	0.0700 (12)	−0.0163 (10)	0.0072 (10)	0.0185 (10)
C26	0.0701 (12)	0.0855 (15)	0.0788 (13)	−0.0094 (11)	0.0323 (10)	0.0165 (11)
C27	0.0709 (12)	0.0576 (11)	0.0762 (12)	0.0005 (9)	0.0319 (10)	0.0046 (9)
C28	0.0492 (9)	0.0438 (9)	0.0417 (8)	0.0051 (7)	0.0146 (7)	−0.0017 (7)
C29	0.0625 (10)	0.0528 (10)	0.0430 (9)	0.0039 (8)	0.0131 (8)	−0.0007 (8)
C30	0.0687 (11)	0.0770 (13)	0.0419 (9)	0.0161 (10)	0.0084 (8)	−0.0043 (9)
C31	0.0595 (11)	0.0835 (14)	0.0515 (10)	0.0049 (10)	0.0050 (8)	−0.0246 (10)
C32	0.0587 (10)	0.0583 (11)	0.0626 (10)	−0.0052 (9)	0.0150 (9)	−0.0194 (9)
C33	0.0552 (10)	0.0494 (10)	0.0476 (9)	0.0014 (8)	0.0122 (7)	−0.0028 (8)
C34	0.0489 (9)	0.0486 (10)	0.0429 (8)	−0.0025 (8)	0.0149 (7)	0.0017 (7)
C35	0.0592 (10)	0.0519 (10)	0.0558 (10)	0.0029 (9)	0.0182 (8)	0.0030 (8)
C36	0.0723 (13)	0.0571 (11)	0.0774 (12)	0.0146 (10)	0.0319 (11)	0.0105 (10)
C37	0.0593 (12)	0.0825 (15)	0.0741 (12)	0.0226 (11)	0.0240 (10)	0.0258 (11)
C38	0.0506 (10)	0.0881 (14)	0.0600 (11)	0.0029 (10)	0.0083 (9)	0.0084 (10)
C39	0.0540 (10)	0.0599 (11)	0.0602 (10)	0.0031 (9)	0.0108 (8)	−0.0005 (9)

Geometric parameters (Å, º)

O—C12	1.3642 (19)	C16—C21	1.4014 (19)
O—C15	1.4221 (19)	C17—C18	1.381 (2)
N—C2	1.340 (2)	C18—C19	1.367 (2)
N—C6	1.3443 (19)	C19—C20	1.377 (2)
N—C1	1.468 (2)	C20—C21	1.382 (2)
B—C22	1.643 (2)	C22—C23	1.386 (2)
B—C28	1.643 (2)	C22—C27	1.400 (2)
B—C34	1.647 (2)	C23—C24	1.386 (2)
B—C16	1.649 (2)	C24—C25	1.360 (2)
C2—C3	1.354 (2)	C25—C26	1.373 (2)
C3—C4	1.397 (2)	C26—C27	1.385 (2)
C4—C5	1.392 (2)	C28—C29	1.3946 (19)
C4—C7	1.449 (2)	C28—C33	1.398 (2)
C5—C6	1.353 (2)	C29—C30	1.386 (2)
C7—C8	1.325 (2)	C30—C31	1.370 (2)
C8—C9	1.453 (2)	C31—C32	1.376 (2)
C9—C10	1.389 (2)	C32—C33	1.385 (2)
C9—C14	1.393 (2)	C34—C39	1.396 (2)
C10—C11	1.370 (2)	C34—C35	1.396 (2)
C11—C12	1.376 (2)	C35—C36	1.391 (2)
C12—C13	1.385 (2)	C36—C37	1.371 (2)
C13—C14	1.372 (2)	C37—C38	1.370 (2)
C16—C17	1.3950 (19)	C38—C39	1.378 (2)
C12—O—C15	118.24 (14)	C21—C16—B	121.08 (12)
C2—N—C6	119.41 (15)	C18—C17—C16	122.94 (15)
C2—N—C1	119.98 (15)	C19—C18—C17	120.55 (15)
C6—N—C1	120.56 (14)	C18—C19—C20	119.09 (15)
C22—B—C28	109.87 (12)	C19—C20—C21	119.71 (15)
C22—B—C34	105.98 (12)	C20—C21—C16	123.34 (14)
C28—B—C34	113.07 (12)	C23—C22—C27	114.32 (14)
C22—B—C16	113.01 (12)	C23—C22—B	127.21 (13)
C28—B—C16	105.12 (11)	C27—C22—B	118.47 (14)
C34—B—C16	109.94 (11)	C22—C23—C24	123.13 (15)
N—C2—C3	120.88 (16)	C25—C24—C23	120.67 (17)
C2—C3—C4	121.34 (16)	C24—C25—C26	118.68 (17)
C5—C4—C3	116.02 (16)	C25—C26—C27	120.24 (16)
C5—C4—C7	123.80 (15)	C26—C27—C22	122.97 (16)
C3—C4—C7	120.16 (15)	C29—C28—C33	114.42 (14)
C6—C5—C4	120.54 (15)	C29—C28—B	124.13 (13)
N—C6—C5	121.72 (15)	C33—C28—B	121.31 (13)
C8—C7—C4	126.42 (16)	C30—C29—C28	123.21 (15)
C7—C8—C9	126.94 (15)	C31—C30—C29	120.09 (16)
C10—C9—C14	116.80 (17)	C30—C31—C32	119.11 (16)
C10—C9—C8	122.48 (15)	C31—C32—C33	119.97 (16)
C14—C9—C8	120.71 (15)	C32—C33—C28	123.17 (15)
C11—C10—C9	122.23 (16)	C39—C34—C35	114.00 (14)
C10—C11—C12	119.97 (16)	C39—C34—B	119.02 (13)
O—C12—C11	123.91 (16)	C35—C34—B	126.98 (14)
O—C12—C13	116.88 (16)	C36—C35—C34	122.74 (16)
C11—C12—C13	119.20 (17)	C37—C36—C35	120.59 (17)
C14—C13—C12	120.37 (16)	C38—C37—C36	118.61 (17)
C13—C14—C9	121.42 (16)	C37—C38—C39	120.13 (18)
C17—C16—C21	114.35 (13)	C38—C39—C34	123.90 (16)
C17—C16—B	124.50 (13)
C6—N—C2—C3	−1.8 (2)	C34—B—C22—C23	−128.17 (15)
C1—N—C2—C3	175.73 (16)	C16—B—C22—C23	−7.7 (2)
N—C2—C3—C4	−0.1 (3)	C28—B—C22—C27	−70.63 (17)
C2—C3—C4—C5	2.6 (2)	C34—B—C22—C27	51.85 (17)
C2—C3—C4—C7	−176.09 (16)	C16—B—C22—C27	172.32 (13)
C3—C4—C5—C6	−3.2 (2)	C27—C22—C23—C24	−0.4 (2)
C7—C4—C5—C6	175.39 (16)	B—C22—C23—C24	179.64 (15)
C2—N—C6—C5	1.1 (2)	C22—C23—C24—C25	0.3 (3)
C1—N—C6—C5	−176.38 (16)	C23—C24—C25—C26	0.0 (3)
C4—C5—C6—N	1.5 (2)	C24—C25—C26—C27	−0.2 (3)
C5—C4—C7—C8	−10.4 (3)	C25—C26—C27—C22	0.1 (3)
C3—C4—C7—C8	168.18 (16)	C23—C22—C27—C26	0.2 (2)
C4—C7—C8—C9	−175.97 (15)	B—C22—C27—C26	−179.80 (16)
C7—C8—C9—C10	−3.9 (3)	C22—B—C28—C29	−9.31 (19)
C7—C8—C9—C14	176.17 (16)	C34—B—C28—C29	−127.49 (15)
C14—C9—C10—C11	0.4 (2)	C16—B—C28—C29	112.57 (15)
C8—C9—C10—C11	−179.47 (16)	C22—B—C28—C33	175.26 (12)
C9—C10—C11—C12	−0.2 (3)	C34—B—C28—C33	57.09 (17)
C15—O—C12—C11	−5.8 (2)	C16—B—C28—C33	−62.85 (16)
C15—O—C12—C13	175.51 (14)	C33—C28—C29—C30	−1.0 (2)
C10—C11—C12—O	−178.95 (16)	B—C28—C29—C30	−176.67 (13)
C10—C11—C12—C13	−0.3 (3)	C28—C29—C30—C31	−0.9 (2)
O—C12—C13—C14	179.23 (15)	C29—C30—C31—C32	1.5 (2)
C11—C12—C13—C14	0.4 (3)	C30—C31—C32—C33	−0.1 (2)
C12—C13—C14—C9	−0.2 (3)	C31—C32—C33—C28	−1.9 (2)
C10—C9—C14—C13	−0.2 (2)	C29—C28—C33—C32	2.4 (2)
C8—C9—C14—C13	179.66 (15)	B—C28—C33—C32	178.20 (13)
C22—B—C16—C17	−123.47 (15)	C22—B—C34—C39	50.68 (16)
C28—B—C16—C17	116.71 (15)	C28—B—C34—C39	171.10 (13)
C34—B—C16—C17	−5.28 (19)	C16—B—C34—C39	−71.76 (16)
C22—B—C16—C21	59.85 (17)	C22—B—C34—C35	−128.85 (14)
C28—B—C16—C21	−59.97 (17)	C28—B—C34—C35	−8.4 (2)
C34—B—C16—C21	178.03 (13)	C16—B—C34—C35	108.71 (16)
C21—C16—C17—C18	0.5 (2)	C39—C34—C35—C36	1.1 (2)
B—C16—C17—C18	−176.39 (15)	B—C34—C35—C36	−179.30 (14)
C16—C17—C18—C19	−1.2 (3)	C34—C35—C36—C37	−1.8 (2)
C17—C18—C19—C20	0.4 (3)	C35—C36—C37—C38	0.7 (2)
C18—C19—C20—C21	0.9 (2)	C36—C37—C38—C39	0.8 (2)
C19—C20—C21—C16	−1.6 (2)	C37—C38—C39—C34	−1.5 (2)
C17—C16—C21—C20	0.9 (2)	C35—C34—C39—C38	0.5 (2)
B—C16—C21—C20	177.89 (13)	B—C34—C39—C38	−179.12 (14)
C28—B—C22—C23	109.35 (16)