1-(2-Methyl­phen­yl)-4,4′-bipyridin-1-ium tetra­fluorido­borate

Crystals of the title compound, C₁₇H₁₅N₂⁺·BF₄⁻, were unexpectedly grown from crystallization attempts of [Pt(4,4′-bpy)₄](BF₄)₂ [Smith et al. (2019). Comments Inorg. Chem. 39, 188–215] using toluene and aceto­nitrile. The tetra­fluoro­borate anion and the central pyridinium ring of the cation are disordered, with atomic site occupancies close to ½. The tolyl group of the cation has a 75.31 (11)° twist relative to the unsubstituted pyridyl group. This rotation allows for a centrosymmetric dimer of cations with weak hydrogen bonding between the pyridyl nitro­gen atom and a methyl H atom on the neighbouring cation.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.108
• wR factor = 0.378
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Datablock: I


Alert level B
PLAT084_ALERT_3_B High wR2 Value (i.e. > 0.25) ...................       0.38 Report

Alert level C
PLAT082_ALERT_2_C High R1 Value ..................................       0.11 Report
PLAT260_ALERT_2_C Large Average Ueq of Residue Including       F1A      0.173 Check
PLAT260_ALERT_2_C Large Average Ueq of Residue Including        F1      0.151 Check
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00558 Ang.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......     18.496 Check
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.917 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.595         14 Report
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          2 Check
PLAT939_ALERT_3_C Large Value of Not (SHELXL) Weight Optimized S .      11.90 Check

Alert level G
PLAT072_ALERT_2_G SHELXL First  Parameter in WGHT  Unusually Large       0.20 Report
PLAT171_ALERT_4_G The CIF-Embedded .res File Contains EADP Records          3 Report
PLAT187_ALERT_4_G The CIF-Embedded .res File Contains RIGU Records          2 Report
PLAT301_ALERT_3_G Main Residue  Disorder ..............(Resd  1  )        21% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  2  )       100% Note
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd  3  )       100% Note
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  2  )       2.54 Check
PLAT304_ALERT_4_G Non-Integer Number of Atoms in ..... (Resd  3  )       2.46 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............         30 Note
PLAT909_ALERT_3_G Percentage of I>2sig(I) Data at Theta(Max) Still        58% Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          1 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File         11 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Info

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
  11 ALERT type 3 Indicator that the structure quality may be low
   7 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2019); cell refinement: CrysAlis PRO (Rigaku OD, 2019); data reduction: CrysAlis PRO (Rigaku OD, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009), Mercury (Macrae et al., 2020); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-(2-Methylphenyl)-4,4'-bipyridin-1-ium tetrafluoridoborate

Crystal data

C17H15N2^+·BF4^−	F(000) = 688
Mr = 334.12	Dx = 1.409 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.4260 (5) Å	Cell parameters from 4873 reflections
b = 9.0735 (3) Å	θ = 4.4–74.8°
c = 15.5434 (5) Å	µ = 1.00 mm^−1
β = 102.118 (4)°	T = 200 K
V = 1575.54 (10) Å^3	Plate, colourless
Z = 4	0.10 × 0.09 × 0.01 mm

Data collection

XtaLAB Synergy, Dualflex, HyPix diffractometer	2786 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2296 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.023
Detector resolution: 10.0000 pixels mm^-1	θmax = 66.6°, θmin = 5.4°
ω scans	h = −13→13
Absorption correction: gaussian (CrysAlis Pro; Rigaku OD, 2019)	k = −8→10
Tmin = 0.845, Tmax = 1.000	l = −18→18
16394 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.108	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.378	H-atom parameters constrained
S = 1.63	w = 1/[σ^2(Fo^2) + (0.2P)^2] where P = (Fo^2 + 2Fc^2)/3
2786 reflections	(Δ/σ)max < 0.001
240 parameters	Δρmax = 0.45 e Å^−3
30 restraints	Δρmin = −0.24 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F1	0.3153 (14)	0.3155 (13)	0.6447 (8)	0.164 (4)	0.493 (6)
F2	0.4760 (14)	0.312 (2)	0.7610 (8)	0.169 (6)	0.493 (6)
F3	0.3583 (14)	0.524 (2)	0.7352 (10)	0.152 (5)	0.493 (6)
F4	0.4860 (11)	0.4406 (9)	0.6437 (8)	0.155 (4)	0.493 (6)
B1	0.415 (3)	0.402 (3)	0.6907 (18)	0.113 (3)	0.493 (6)
F1A	0.3290 (16)	0.530 (2)	0.7158 (11)	0.145 (5)	0.507 (6)
F2A	0.4771 (16)	0.372 (2)	0.7621 (12)	0.202 (8)	0.507 (6)
F3A	0.4091 (17)	0.418 (2)	0.6267 (7)	0.214 (9)	0.507 (6)
F4A	0.2994 (13)	0.3047 (13)	0.7003 (10)	0.193 (5)	0.507 (6)
B1A	0.380 (2)	0.409 (3)	0.7088 (17)	0.113 (3)	0.507 (6)
N1	0.2687 (4)	0.9335 (5)	0.3262 (2)	0.1134 (9)
N2	0.4946 (2)	0.8531 (3)	0.78218 (17)	0.0764 (8)
C1	0.2431 (4)	1.0258 (6)	0.3851 (3)	0.1134 (9)
H1	0.190962	1.102669	0.364388	0.136*
C2	0.2866 (4)	1.0187 (5)	0.4745 (3)	0.0982 (12)
H2	0.264380	1.088352	0.511920	0.118*
C3	0.3641 (3)	0.9056 (4)	0.5073 (2)	0.0768 (9)
C4	0.3920 (4)	0.8102 (5)	0.4469 (2)	0.0979 (12)
H4	0.443970	0.732164	0.465446	0.118*
C5	0.3441 (4)	0.8285 (6)	0.3586 (3)	0.1134 (9)
H5	0.366517	0.762100	0.319478	0.136*
C6	0.3935 (8)	0.9217 (10)	0.7527 (5)	0.0836 (12)	0.493 (6)
H6	0.349547	0.957945	0.792095	0.100*	0.493 (6)
C7	0.3526 (8)	0.9402 (9)	0.6654 (5)	0.0836 (12)	0.493 (6)
H7	0.281258	0.991286	0.646357	0.100*	0.493 (6)
C8	0.4113 (3)	0.8872 (3)	0.60354 (19)	0.0694 (8)
C9	0.5101 (8)	0.7906 (12)	0.6389 (7)	0.0836 (12)	0.493 (6)
H9	0.547025	0.737002	0.601039	0.100*	0.493 (6)
C10	0.5484 (9)	0.7783 (13)	0.7254 (8)	0.0836 (12)	0.493 (6)
H10	0.613277	0.717412	0.747470	0.100*	0.493 (6)
C11	0.5354 (3)	0.8302 (4)	0.8786 (2)	0.0833 (10)
C12	0.6227 (3)	0.9222 (4)	0.9257 (2)	0.0893 (11)
C13	0.6571 (4)	0.8949 (5)	1.0169 (2)	0.0947 (11)
H13	0.716373	0.952582	1.051149	0.114*
C14	0.6053 (4)	0.7857 (5)	1.0553 (2)	0.1002 (13)
H14	0.629212	0.770262	1.115608	0.120*
C15	0.5208 (5)	0.7005 (5)	1.0085 (3)	0.1115 (14)
H15	0.486885	0.625935	1.036254	0.134*
C16	0.4823 (4)	0.7217 (5)	0.9174 (2)	0.1013 (12)
H16	0.422234	0.663387	0.884552	0.122*
C17	0.6795 (5)	1.0384 (6)	0.8840 (3)	0.1146 (14)
H17A	0.699061	1.001150	0.830901	0.172*
H17B	0.751317	1.070252	0.923432	0.172*
H17C	0.625551	1.120184	0.870080	0.172*
C6A	0.5156 (8)	0.7563 (13)	0.7254 (8)	0.0836 (12)	0.507 (6)
H6A	0.560901	0.673187	0.745238	0.100*	0.507 (6)
C7A	0.4714 (8)	0.7748 (12)	0.6354 (7)	0.0836 (12)	0.507 (6)
H7A	0.486638	0.701903	0.597120	0.100*	0.507 (6)
C9A	0.3999 (7)	1.0067 (10)	0.6624 (5)	0.0836 (12)	0.507 (6)
H9A	0.367388	1.096731	0.640958	0.100*	0.507 (6)
C10A	0.4385 (7)	0.9833 (9)	0.7510 (5)	0.0836 (12)	0.507 (6)
H10A	0.426844	1.055966	0.790597	0.100*	0.507 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.204 (9)	0.136 (6)	0.124 (7)	−0.009 (5)	−0.031 (7)	0.010 (6)
F2	0.148 (7)	0.277 (17)	0.081 (5)	0.003 (8)	0.023 (4)	0.057 (7)
F3	0.141 (8)	0.197 (11)	0.134 (10)	−0.064 (7)	0.068 (8)	−0.078 (8)
F4	0.212 (9)	0.108 (4)	0.184 (9)	0.036 (5)	0.129 (8)	0.021 (4)
B1	0.133 (14)	0.138 (5)	0.064 (10)	−0.010 (7)	0.013 (5)	0.003 (5)
F1A	0.168 (10)	0.168 (9)	0.093 (5)	0.019 (8)	0.011 (5)	0.007 (6)
F2A	0.160 (9)	0.250 (16)	0.165 (11)	0.061 (10)	−0.038 (7)	−0.008 (9)
F3A	0.270 (15)	0.282 (17)	0.102 (5)	0.184 (15)	0.066 (8)	0.042 (7)
F4A	0.208 (9)	0.140 (6)	0.200 (12)	−0.022 (5)	−0.026 (11)	−0.006 (8)
B1A	0.133 (14)	0.138 (5)	0.064 (10)	−0.010 (7)	0.013 (5)	0.003 (5)
N1	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
N2	0.0827 (15)	0.0889 (17)	0.0585 (15)	0.0092 (12)	0.0171 (11)	−0.0079 (11)
C1	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
C2	0.114 (3)	0.110 (3)	0.067 (2)	−0.004 (2)	0.0120 (18)	0.0072 (18)
C3	0.0793 (17)	0.093 (2)	0.0607 (18)	−0.0261 (15)	0.0203 (13)	−0.0015 (14)
C4	0.112 (3)	0.119 (3)	0.065 (2)	−0.007 (2)	0.0234 (19)	−0.0141 (18)
C5	0.1264 (19)	0.146 (2)	0.0661 (14)	−0.0230 (14)	0.0169 (12)	−0.0021 (12)
C6	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C7	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C8	0.0727 (15)	0.0772 (17)	0.0618 (18)	−0.0103 (12)	0.0219 (12)	−0.0022 (12)
C9	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C10	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C11	0.0872 (19)	0.095 (2)	0.068 (2)	0.0171 (16)	0.0167 (15)	−0.0106 (15)
C12	0.099 (2)	0.102 (2)	0.069 (2)	0.0096 (18)	0.0222 (17)	−0.0071 (16)
C13	0.106 (2)	0.116 (3)	0.061 (2)	0.027 (2)	0.0174 (17)	−0.0113 (18)
C14	0.126 (3)	0.113 (3)	0.063 (2)	0.032 (2)	0.023 (2)	−0.0025 (19)
C15	0.140 (3)	0.121 (3)	0.078 (2)	0.009 (3)	0.031 (2)	0.008 (2)
C16	0.129 (3)	0.115 (3)	0.063 (2)	0.000 (2)	0.029 (2)	0.0048 (18)
C17	0.128 (3)	0.137 (4)	0.074 (2)	−0.015 (3)	0.011 (2)	−0.004 (2)
C6A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C7A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C9A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)
C10A	0.096 (3)	0.093 (2)	0.0613 (12)	0.0127 (19)	0.0175 (19)	−0.0097 (14)

Geometric parameters (Å, º)

F1—B1	1.44 (3)	C7—C8	1.369 (8)
F2—B1	1.42 (3)	C8—C9	1.444 (11)
F3—B1	1.52 (3)	C8—C7A	1.271 (11)
F4—B1	1.248 (19)	C8—C9A	1.442 (8)
F1A—B1A	1.26 (3)	C9—H9	0.9300
F2A—B1A	1.28 (4)	C9—C10	1.329 (12)
F3A—B1A	1.39 (2)	C10—H10	0.9300
F4A—B1A	1.31 (3)	C11—C12	1.387 (5)
N1—C1	1.319 (6)	C11—C16	1.362 (5)
N1—C5	1.312 (7)	C12—C13	1.411 (5)
N2—C6	1.307 (8)	C12—C17	1.460 (6)
N2—C10	1.359 (11)	C13—H13	0.9300
N2—C11	1.487 (4)	C13—C14	1.356 (6)
N2—C6A	1.303 (11)	C14—H14	0.9300
N2—C10A	1.382 (8)	C14—C15	1.328 (6)
C1—H1	0.9300	C15—H15	0.9300
C1—C2	1.375 (6)	C15—C16	1.405 (5)
C2—H2	0.9300	C16—H16	0.9300
C2—C3	1.381 (5)	C17—H17A	0.9600
C3—C4	1.363 (5)	C17—H17B	0.9600
C3—C8	1.489 (4)	C17—H17C	0.9600
C4—H4	0.9300	C6A—C7A	1.393 (12)
C4—C5	1.376 (6)	C6A—H6A	0.9300
C5—H5	0.9300	C7A—H7A	0.9300
C6—H6	0.9300	C9A—C10A	1.372 (9)
C6—C7	1.350 (9)	C9A—H9A	0.9300
C7—H7	0.9300	C10A—H10A	0.9300
F2—B1—F1	106.1 (19)	C7A—C8—C9A	118.0 (6)
F2—B1—F3	104.7 (18)	C9A—C8—C3	119.5 (4)
F4—B1—F2	110 (2)	C8—C9—H9	119.9
F4—B1—F1	114 (2)	C10—C9—C8	120.1 (7)
F4—B1—F3	117 (2)	C10—C9—H9	119.9
F1—B1—F3	104.4 (19)	N2—C10—H10	119.4
F1A—B1A—F2A	122 (3)	C9—C10—N2	121.1 (8)
F1A—B1A—F3A	103 (2)	C9—C10—H10	119.4
F1A—B1A—F4A	108 (2)	C12—C11—N2	119.2 (3)
F2A—B1A—F3A	105.7 (17)	C16—C11—N2	118.2 (3)
F2A—B1A—F4A	112 (2)	C16—C11—C12	122.6 (3)
F4A—B1A—F3A	105 (2)	C11—C12—C13	116.3 (4)
C5—N1—C1	114.6 (4)	C11—C12—C17	122.5 (3)
C6—N2—C10	119.8 (6)	C13—C12—C17	121.2 (4)
C6—N2—C11	119.1 (4)	C12—C13—H13	119.5
C10—N2—C11	119.7 (6)	C14—C13—C12	121.1 (4)
C6A—N2—C11	121.7 (6)	C14—C13—H13	119.5
C6A—N2—C10A	118.5 (6)	C13—C14—H14	119.4
C10A—N2—C11	119.8 (4)	C15—C14—C13	121.2 (4)
N1—C1—H1	117.0	C15—C14—H14	119.4
N1—C1—C2	125.9 (5)	C14—C15—H15	119.6
C2—C1—H1	117.0	C14—C15—C16	120.7 (4)
C1—C2—H2	120.8	C16—C15—H15	119.6
C1—C2—C3	118.4 (4)	C11—C16—C15	118.1 (4)
C3—C2—H2	120.8	C11—C16—H16	120.9
C2—C3—C8	121.5 (3)	C15—C16—H16	120.9
C4—C3—C2	116.2 (3)	C12—C17—H17A	109.5
C4—C3—C8	122.2 (3)	C12—C17—H17B	109.5
C3—C4—H4	119.7	C12—C17—H17C	109.5
C3—C4—C5	120.5 (4)	H17A—C17—H17B	109.5
C5—C4—H4	119.7	H17A—C17—H17C	109.5
N1—C5—C4	124.3 (4)	H17B—C17—H17C	109.5
N1—C5—H5	117.9	C8—C7A—H7A	118.7
C4—C5—H5	117.9	C8—C7A—C6A	122.7 (8)
N2—C6—H6	119.8	N2—C6A—C7A	121.3 (9)
N2—C6—C7	120.4 (6)	N2—C6A—H6A	119.4
C7—C6—H6	119.8	N2—C10A—H10A	119.6
C6—C7—H7	118.5	C8—C9A—H9A	121.0
C6—C7—C8	123.0 (6)	C6A—C7A—H7A	118.7
C8—C7—H7	118.5	C7A—C6A—H6A	119.4
C7—C8—C3	122.6 (4)	C9A—C10A—N2	120.8 (6)
C7—C8—C9	113.9 (5)	C9A—C10A—H10A	119.6
C9—C8—C3	122.6 (5)	C10A—C9A—C8	117.9 (6)
C7A—C8—C3	122.2 (5)	C10A—C9A—H9A	121.0
N1—C1—C2—C3	−0.1 (6)	C7—C8—C9—C10	−10.3 (10)
N2—C6—C7—C8	1.4 (12)	C8—C3—C4—C5	178.2 (3)
N2—C11—C12—C13	179.8 (3)	C8—C9—C10—N2	1.4 (11)
N2—C11—C12—C17	−2.1 (5)	C8—C7A—C6A—N2	1.7 (11)
N2—C11—C16—C15	−179.9 (3)	C10—N2—C6—C7	−11.3 (11)
N2—C10A—C9A—C8	4.7 (11)	C10—N2—C11—C12	92.2 (6)
C1—N1—C5—C4	1.6 (7)	C10—N2—C11—C16	−89.8 (6)
C1—C2—C3—C4	0.7 (5)	C11—N2—C6—C7	−178.1 (6)
C1—C2—C3—C8	−177.6 (3)	C11—N2—C10—C9	176.6 (6)
C2—C3—C4—C5	−0.1 (5)	C11—N2—C6A—C7A	176.5 (5)
C2—C3—C8—C7	24.5 (6)	C11—N2—C10A—C9A	−179.9 (6)
C2—C3—C8—C9	−166.9 (6)	C11—C12—C13—C14	−1.1 (5)
C2—C3—C8—C7A	171.8 (6)	C12—C11—C16—C15	−1.9 (6)
C2—C3—C8—C9A	−14.9 (6)	C12—C13—C14—C15	0.4 (6)
C3—C4—C5—N1	−1.1 (7)	C13—C14—C15—C16	−0.4 (6)
C3—C8—C9—C10	−179.9 (5)	C14—C15—C16—C11	1.1 (6)
C3—C8—C7A—C6A	−179.7 (5)	C16—C11—C12—C13	1.9 (5)
C3—C8—C9A—C10A	176.6 (5)	C16—C11—C12—C17	180.0 (4)
C4—C3—C8—C7	−153.7 (6)	C17—C12—C13—C14	−179.2 (4)
C4—C3—C8—C9	14.9 (6)	C7A—C8—C9A—C10A	−9.8 (10)
C4—C3—C8—C7A	−6.4 (7)	C6A—N2—C11—C12	113.3 (6)
C4—C3—C8—C9A	166.9 (5)	C6A—N2—C11—C16	−68.7 (6)
C5—N1—C1—C2	−1.0 (7)	C6A—N2—C10A—C9A	3.6 (10)
C6—N2—C10—C9	9.9 (11)	C10A—N2—C11—C12	−63.2 (6)
C6—N2—C11—C12	−101.0 (6)	C10A—N2—C11—C16	114.9 (5)
C6—N2—C11—C16	77.0 (6)	C10A—N2—C6A—C7A	−7.0 (9)
C6—C7—C8—C3	178.7 (6)	C9A—C8—C7A—C6A	6.9 (10)
C6—C7—C8—C9	9.2 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17A···N1^i	0.96	2.61	3.450 (6)	146

Symmetry code: (i) −x+1, −y+2, −z+1.