1,1′-(1,4-Phenyl­enedimethyl­ene)­dipyridinium bis­(tetra­phenyl­borate)

Wu, Y.-J.; Liu, X.-C.; Du, C.-X.; Niu, Y.-Y.

doi:10.1107/S1600536807032588

1,1′-(1,4-Phenylenedimethylene)dipyridinium bis(tetraphenylborate)

Y.-J. Wu, X.-C. Liu, C.-X. Du and Y.-Y. Niu

The title compound, C₁₈H₁₈N₂²⁺·2B(C₆H₅)₄⁻, consists of a 1,1′-(1,4-phenylenedimethylene)dipyridinium cation located on an inversion center and two tetraphenylborate anions. There are C—H

π interactions of intermediate strength between the pyridinium group of the cation and the surrounding anions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032588/is2181sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032588/is2181Isup2.hkl Contains datablock I

CCDC reference: 657734

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Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R factor = 0.058
wR factor = 0.149
Data-to-parameter ratio = 15.2

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No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The tetraphenylborate ion, BPh₄^-, has been widely used as a counterion in cation complex systems. These cations include metal atoms, organic ammonium cations, bipyridinium cations and arenediazonium cations (Kiviniemi et al., 2001). In our previous studies we have investigated the organo-inorganic hybrid compounds containing the 1,ω-alkylidene dipyridine cations (Liu, Liao et al., 2007; Liu, Shi et al., 2007). Herein we report the crystal structure of 1,1'-(1,4-phenylenedimethylene)dipyridinium cation with tetraphenylborate.

The asymmetric unit of the title compound (Fig. 1), (C₁₈H₁₈N₂)_0.5.B(C₆H₅)₄, contains half a 1,1'-(1,4-phenylenedimethylene)dipyridinium cation and one tetraphenylborate anion; the cation is located on an inversion center. The cation is surrounded by four anions and interacts with three of them via C—H···π interactions (Table 1 and Fig. 2).

Related literature top

For related literature, see: Kiviniemi et al. (2001); Liu, Liao et al. (2007); Liu, Shi et al. (2007). Cg1, Cg2 and Cg3 are the centroids of the C16–C21, C22–C27 and C28–C33 phenyl rings, respectively.

Experimental top

All chemicals used were purchased from Jinan Henghua Sci. & Tec. Co., Ltd. The salt was synthesized from the reaction of 1,1'-(1,4-phenylenedimethylene)dipyridinium dichloride (0.033 g, 0.1 mmol) in methanol (5 ml) and Na[BPh₄] (0.034 g, 0.1 mmol) in DMF (10 ml). The mixture was set aside for the formation of colorless crystals in 54% yield after several days. Anal. Calc. for C₃₃H₂₉BN: C 88.00, H 6.44, N 3.11%; Found: C 87.96, H 6.47, N 3.07%.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Atoms labeled with I are at the symmetry position (-x + 2, -y + 2, -z + 1).
	Fig. 2. A partial packing diagram of the title compound, showing C—H···π interactions (dashed lines).

1,1'-(1,4-Phenylenedimethylene)dipyridinium bis(tetraphenylborate) top

Crystal data top

C₁₈H₁₈N₂²⁺·2C₂₄H₂₀B⁻	Z = 1
M_r = 900.76	F(000) = 478
Triclinic, P1	D_x = 1.200 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8194 (8) Å	Cell parameters from 1607 reflections
b = 10.3074 (9) Å	θ = 1.5–26.0°
c = 13.3980 (12) Å	µ = 0.07 mm⁻¹
α = 97.224 (2)°	T = 298 K
β = 92.143 (2)°	Plate, colorless
γ = 111.530 (2)°	0.40 × 0.20 × 0.06 mm
V = 1246.28 (19) Å³

Data collection top

Bruker APEX II CCD area-detector diffractometer	3179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.038
Graphite monochromator	θ_max = 26.0°, θ_min = 1.5°
φ and ω scans	h = −12→8
9445 measured reflections	k = −12→12
4794 independent reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H-atom parameters not refined
S = 1.00	w = 1/[σ²(F_o²) + (0.0666P)²] where P = (F_o² + 2F_c²)/3
4794 reflections	(Δ/σ)_max = 0.008
316 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₈H₁₈N₂²⁺·2C₂₄H₂₀B⁻	γ = 111.530 (2)°
M_r = 900.76	V = 1246.28 (19) Å³
Triclinic, P1	Z = 1
a = 9.8194 (8) Å	Mo Kα radiation
b = 10.3074 (9) Å	µ = 0.07 mm⁻¹
c = 13.3980 (12) Å	T = 298 K
α = 97.224 (2)°	0.40 × 0.20 × 0.06 mm
β = 92.143 (2)°

Data collection top

Bruker APEX II CCD area-detector diffractometer	3179 reflections with I > 2σ(I)
9445 measured reflections	R_int = 0.038
4794 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.149	H-atom parameters not refined
S = 1.00	Δρ_max = 0.22 e Å⁻³
4794 reflections	Δρ_min = −0.18 e Å⁻³
316 parameters

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

	x	y	z	U_iso*/U_eq
B1	0.2031 (2)	0.5217 (2)	0.23828 (15)	0.0340 (5)
C1	0.6064 (2)	0.9191 (2)	0.28743 (14)	0.0455 (6)
H1	0.5622	0.8386	0.3171	0.055*
C2	0.5276 (2)	0.9974 (2)	0.26334 (15)	0.0499 (6)
H2	0.4295	0.9705	0.2767	0.060*
C3	0.5923 (3)	1.1152 (2)	0.21966 (16)	0.0551 (6)
H3	0.5396	1.1701	0.2046	0.066*
C4	0.7366 (3)	1.1521 (2)	0.19802 (16)	0.0552 (6)
H4	0.7814	1.2308	0.1667	0.066*
C5	0.8125 (2)	1.0725 (2)	0.22287 (16)	0.0505 (6)
H5	0.9099	1.0967	0.2085	0.061*
C6	0.8356 (3)	0.8804 (2)	0.30283 (16)	0.0551 (6)
H6A	0.9058	0.8784	0.2542	0.066*
H6B	0.7710	0.7838	0.3052	0.066*
C7	0.9178 (2)	0.9449 (2)	0.40600 (15)	0.0422 (5)
C8	0.9777 (2)	0.8658 (2)	0.45543 (16)	0.0507 (6)
H8	0.9631	0.7745	0.4260	0.061*
C9	1.0587 (3)	0.9201 (2)	0.54765 (17)	0.0539 (6)
H9	1.0984	0.8650	0.5793	0.065*
C10	0.2930 (2)	0.61470 (19)	0.15340 (13)	0.0339 (5)
C11	0.4208 (2)	0.5992 (2)	0.12074 (14)	0.0415 (5)
H11	0.4465	0.5281	0.1420	0.050*
C12	0.5106 (2)	0.6841 (2)	0.05859 (16)	0.0500 (6)
H12	0.5949	0.6701	0.0396	0.060*
C13	0.4750 (3)	0.7892 (2)	0.02493 (15)	0.0529 (6)
H13	0.5346	0.8467	−0.0171	0.064*
C14	0.3507 (3)	0.8083 (2)	0.05401 (16)	0.0509 (6)
H14	0.3252	0.8786	0.0311	0.061*
C15	0.2626 (2)	0.7235 (2)	0.11752 (14)	0.0420 (5)
H15	0.1797	0.7399	0.1370	0.050*
C16	0.3055 (2)	0.60729 (18)	0.34397 (13)	0.0335 (5)
C17	0.4272 (2)	0.5815 (2)	0.38034 (14)	0.0395 (5)
H17	0.4453	0.5050	0.3478	0.047*
C18	0.5221 (2)	0.6652 (2)	0.46290 (16)	0.0507 (6)
H18	0.6019	0.6443	0.4844	0.061*
C19	0.4984 (3)	0.7787 (2)	0.51278 (16)	0.0578 (7)
H19	0.5613	0.8347	0.5683	0.069*
C20	0.3803 (3)	0.8085 (2)	0.47958 (16)	0.0552 (6)
H20	0.3636	0.8856	0.5125	0.066*
C21	0.2863 (2)	0.7241 (2)	0.39730 (14)	0.0425 (5)
H21	0.2069	0.7461	0.3766	0.051*
C22	0.1924 (2)	0.35750 (19)	0.21150 (14)	0.0371 (5)
C23	0.1626 (2)	0.2894 (2)	0.11149 (17)	0.0548 (6)
H23	0.1498	0.3392	0.0610	0.066*
C24	0.1514 (3)	0.1520 (3)	0.0841 (2)	0.0778 (9)
H24	0.1314	0.1112	0.0165	0.093*
C25	0.1699 (3)	0.0756 (3)	0.1571 (3)	0.0847 (10)
H25	0.1644	−0.0165	0.1391	0.102*
C26	0.1965 (3)	0.1365 (3)	0.2568 (3)	0.0727 (8)
H26	0.2087	0.0857	0.3068	0.087*
C27	0.2053 (2)	0.2746 (2)	0.28269 (18)	0.0525 (6)
H27	0.2205	0.3131	0.3507	0.063*
C28	0.0339 (2)	0.51288 (19)	0.24453 (14)	0.0367 (5)
C29	−0.0361 (2)	0.4910 (2)	0.33345 (16)	0.0471 (6)
H29	0.0169	0.4856	0.3907	0.056*
C30	−0.1818 (3)	0.4770 (2)	0.3396 (2)	0.0636 (7)
H30	−0.2243	0.4625	0.4001	0.076*
C31	−0.2631 (3)	0.4847 (3)	0.2560 (2)	0.0695 (8)
H31	−0.3598	0.4778	0.2602	0.083*
C32	−0.2002 (3)	0.5025 (2)	0.1667 (2)	0.0633 (7)
H32	−0.2547	0.5061	0.1095	0.076*
C33	−0.0560 (2)	0.5152 (2)	0.16148 (17)	0.0478 (6)
H33	−0.0163	0.5259	0.0997	0.057*
N1	0.74748 (19)	0.95834 (17)	0.26829 (12)	0.0426 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0316 (12)	0.0335 (11)	0.0338 (12)	0.0088 (9)	0.0024 (9)	0.0047 (9)
C1	0.0451 (13)	0.0409 (12)	0.0370 (11)	0.0012 (10)	0.0015 (10)	0.0042 (9)
C2	0.0422 (13)	0.0529 (14)	0.0466 (13)	0.0113 (11)	−0.0045 (10)	0.0013 (10)
C3	0.0562 (16)	0.0518 (14)	0.0544 (14)	0.0204 (12)	−0.0155 (12)	0.0031 (11)
C4	0.0580 (16)	0.0441 (13)	0.0564 (14)	0.0088 (11)	−0.0043 (12)	0.0169 (10)
C5	0.0403 (13)	0.0487 (13)	0.0534 (13)	0.0047 (10)	0.0035 (10)	0.0120 (11)
C6	0.0610 (16)	0.0481 (13)	0.0570 (14)	0.0246 (12)	−0.0064 (12)	0.0007 (11)
C7	0.0412 (12)	0.0399 (11)	0.0472 (12)	0.0165 (9)	0.0046 (9)	0.0087 (9)
C8	0.0609 (15)	0.0400 (12)	0.0554 (14)	0.0260 (11)	−0.0008 (11)	0.0018 (10)
C9	0.0638 (16)	0.0484 (13)	0.0573 (14)	0.0314 (12)	−0.0077 (11)	0.0073 (11)
C10	0.0326 (11)	0.0337 (10)	0.0307 (10)	0.0084 (8)	0.0005 (8)	0.0010 (8)
C11	0.0394 (12)	0.0414 (11)	0.0428 (11)	0.0134 (9)	0.0051 (9)	0.0081 (9)
C12	0.0419 (13)	0.0538 (14)	0.0482 (13)	0.0103 (11)	0.0135 (10)	0.0066 (11)
C13	0.0594 (16)	0.0486 (13)	0.0386 (12)	0.0035 (12)	0.0122 (11)	0.0126 (10)
C14	0.0611 (15)	0.0407 (12)	0.0473 (13)	0.0126 (11)	0.0037 (11)	0.0132 (10)
C15	0.0453 (12)	0.0374 (11)	0.0411 (11)	0.0129 (10)	0.0037 (9)	0.0061 (9)
C16	0.0304 (11)	0.0321 (10)	0.0350 (10)	0.0063 (8)	0.0059 (8)	0.0105 (8)
C17	0.0361 (12)	0.0359 (10)	0.0423 (11)	0.0082 (9)	0.0001 (9)	0.0087 (9)
C18	0.0421 (13)	0.0533 (14)	0.0511 (13)	0.0093 (10)	−0.0074 (10)	0.0174 (11)
C19	0.0550 (15)	0.0604 (15)	0.0401 (12)	0.0045 (12)	−0.0103 (11)	0.0009 (11)
C20	0.0576 (15)	0.0479 (13)	0.0471 (13)	0.0092 (11)	0.0058 (11)	−0.0072 (10)
C21	0.0387 (12)	0.0423 (12)	0.0432 (11)	0.0132 (9)	0.0040 (9)	0.0007 (9)
C22	0.0265 (10)	0.0347 (10)	0.0469 (12)	0.0075 (8)	0.0056 (9)	0.0057 (9)
C23	0.0566 (15)	0.0389 (12)	0.0555 (14)	0.0050 (10)	0.0167 (11)	−0.0040 (10)
C24	0.0744 (19)	0.0477 (15)	0.088 (2)	0.0017 (14)	0.0370 (16)	−0.0168 (15)
C25	0.0541 (17)	0.0379 (14)	0.159 (3)	0.0157 (13)	0.0357 (19)	−0.0005 (19)
C26	0.0406 (14)	0.0446 (14)	0.134 (3)	0.0135 (11)	−0.0015 (15)	0.0274 (16)
C27	0.0370 (12)	0.0394 (12)	0.0757 (16)	0.0078 (10)	−0.0050 (11)	0.0118 (11)
C28	0.0326 (11)	0.0292 (10)	0.0435 (11)	0.0074 (8)	0.0024 (9)	0.0015 (8)
C29	0.0352 (12)	0.0446 (12)	0.0528 (13)	0.0065 (9)	0.0080 (10)	0.0012 (10)
C30	0.0471 (15)	0.0517 (14)	0.0799 (18)	0.0079 (11)	0.0253 (13)	−0.0061 (12)
C31	0.0325 (13)	0.0546 (15)	0.118 (2)	0.0180 (11)	0.0076 (15)	−0.0039 (15)
C32	0.0392 (14)	0.0535 (15)	0.095 (2)	0.0164 (11)	−0.0103 (14)	0.0091 (13)
C33	0.0361 (12)	0.0430 (12)	0.0600 (14)	0.0099 (9)	−0.0022 (10)	0.0092 (10)
N1	0.0456 (11)	0.0380 (9)	0.0397 (10)	0.0108 (8)	−0.0036 (8)	0.0062 (7)

Geometric parameters (Å, º) top

B1—C28	1.637 (3)	C15—H15	0.9300
B1—C10	1.649 (3)	C16—C21	1.399 (3)
B1—C22	1.649 (3)	C16—C17	1.399 (3)
B1—C16	1.650 (3)	C17—C18	1.389 (3)
C1—N1	1.338 (3)	C17—H17	0.9300
C1—C2	1.364 (3)	C18—C19	1.373 (3)
C1—H1	0.9300	C18—H18	0.9300
C2—C3	1.364 (3)	C19—C20	1.376 (3)
C2—H2	0.9300	C19—H19	0.9300
C3—C4	1.378 (3)	C20—C21	1.385 (3)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.356 (3)	C21—H21	0.9300
C4—H4	0.9300	C22—C27	1.390 (3)
C5—N1	1.349 (3)	C22—C23	1.399 (3)
C5—H5	0.9300	C23—C24	1.380 (3)
C6—N1	1.477 (3)	C23—H23	0.9300
C6—C7	1.515 (3)	C24—C25	1.377 (4)
C6—H6A	0.9700	C24—H24	0.9300
C6—H6B	0.9700	C25—C26	1.375 (4)
C7—C8	1.381 (3)	C25—H25	0.9300
C7—C9ⁱ	1.383 (3)	C26—C27	1.392 (3)
C8—C9	1.378 (3)	C26—H26	0.9300
C8—H8	0.9300	C27—H27	0.9300
C9—C7ⁱ	1.383 (3)	C28—C29	1.399 (3)
C9—H9	0.9300	C28—C33	1.402 (3)
C10—C15	1.396 (3)	C29—C30	1.391 (3)
C10—C11	1.401 (3)	C29—H29	0.9300
C11—C12	1.381 (3)	C30—C31	1.379 (4)
C11—H11	0.9300	C30—H30	0.9300
C12—C13	1.375 (3)	C31—C32	1.369 (4)
C12—H12	0.9300	C31—H31	0.9300
C13—C14	1.368 (3)	C32—C33	1.378 (3)
C13—H13	0.9300	C32—H32	0.9300
C14—C15	1.387 (3)	C33—H33	0.9300
C14—H14	0.9300

C28—B1—C10	114.81 (16)	C17—C16—B1	123.67 (16)
C28—B1—C22	106.03 (15)	C18—C17—C16	122.81 (19)
C10—B1—C22	109.62 (16)	C18—C17—H17	118.6
C28—B1—C16	111.05 (15)	C16—C17—H17	118.6
C10—B1—C16	101.99 (14)	C19—C18—C17	120.1 (2)
C22—B1—C16	113.55 (16)	C19—C18—H18	120.0
N1—C1—C2	119.8 (2)	C17—C18—H18	120.0
N1—C1—H1	120.1	C18—C19—C20	119.19 (19)
C2—C1—H1	120.1	C18—C19—H19	120.4
C1—C2—C3	120.1 (2)	C20—C19—H19	120.4
C1—C2—H2	120.0	C19—C20—C21	120.2 (2)
C3—C2—H2	120.0	C19—C20—H20	119.9
C2—C3—C4	119.4 (2)	C21—C20—H20	119.9
C2—C3—H3	120.3	C20—C21—C16	122.9 (2)
C4—C3—H3	120.3	C20—C21—H21	118.6
C5—C4—C3	119.3 (2)	C16—C21—H21	118.6
C5—C4—H4	120.4	C27—C22—C23	114.86 (19)
C3—C4—H4	120.4	C27—C22—B1	124.77 (17)
N1—C5—C4	120.4 (2)	C23—C22—B1	120.32 (18)
N1—C5—H5	119.8	C24—C23—C22	123.2 (2)
C4—C5—H5	119.8	C24—C23—H23	118.4
N1—C6—C7	112.98 (16)	C22—C23—H23	118.4
N1—C6—H6A	109.0	C25—C24—C23	119.8 (3)
C7—C6—H6A	109.0	C25—C24—H24	120.1
N1—C6—H6B	109.0	C23—C24—H24	120.1
C7—C6—H6B	109.0	C26—C25—C24	119.4 (2)
H6A—C6—H6B	107.8	C26—C25—H25	120.3
C8—C7—C9ⁱ	117.79 (19)	C24—C25—H25	120.3
C8—C7—C6	118.02 (18)	C25—C26—C27	119.7 (3)
C9ⁱ—C7—C6	124.15 (19)	C25—C26—H26	120.1
C9—C8—C7	121.02 (19)	C27—C26—H26	120.1
C9—C8—H8	119.5	C22—C27—C26	122.9 (2)
C7—C8—H8	119.5	C22—C27—H27	118.5
C8—C9—C7ⁱ	121.2 (2)	C26—C27—H27	118.5
C8—C9—H9	119.4	C29—C28—C33	114.58 (19)
C7ⁱ—C9—H9	119.4	C29—C28—B1	121.42 (17)
C15—C10—C11	114.40 (18)	C33—C28—B1	123.82 (18)
C15—C10—B1	125.01 (18)	C30—C29—C28	122.6 (2)
C11—C10—B1	120.16 (17)	C30—C29—H29	118.7
C12—C11—C10	123.4 (2)	C28—C29—H29	118.7
C12—C11—H11	118.3	C31—C30—C29	120.0 (2)
C10—C11—H11	118.3	C31—C30—H30	120.0
C13—C12—C11	119.8 (2)	C29—C30—H30	120.0
C13—C12—H12	120.1	C32—C31—C30	119.3 (2)
C11—C12—H12	120.1	C32—C31—H31	120.3
C14—C13—C12	119.2 (2)	C30—C31—H31	120.3
C14—C13—H13	120.4	C31—C32—C33	120.0 (2)
C12—C13—H13	120.4	C31—C32—H32	120.0
C13—C14—C15	120.4 (2)	C33—C32—H32	120.0
C13—C14—H14	119.8	C32—C33—C28	123.4 (2)
C15—C14—H14	119.8	C32—C33—H33	118.3
C14—C15—C10	122.8 (2)	C28—C33—H33	118.3
C14—C15—H15	118.6	C1—N1—C5	121.03 (19)
C10—C15—H15	118.6	C1—N1—C6	119.39 (18)
C21—C16—C17	114.86 (16)	C5—N1—C6	119.48 (19)
C21—C16—B1	121.03 (17)

N1—C1—C2—C3	0.1 (3)	B1—C16—C21—C20	−172.40 (19)
C1—C2—C3—C4	1.6 (3)	C28—B1—C22—C27	−94.2 (2)
C2—C3—C4—C5	−1.6 (3)	C10—B1—C22—C27	141.32 (19)
C3—C4—C5—N1	0.0 (3)	C16—B1—C22—C27	28.0 (3)
N1—C6—C7—C8	166.3 (2)	C28—B1—C22—C23	83.1 (2)
N1—C6—C7—C9ⁱ	−16.1 (3)	C10—B1—C22—C23	−41.4 (2)
C9ⁱ—C7—C8—C9	−0.3 (4)	C16—B1—C22—C23	−154.74 (18)
C6—C7—C8—C9	177.4 (2)	C27—C22—C23—C24	−2.1 (3)
C7—C8—C9—C7ⁱ	0.3 (4)	B1—C22—C23—C24	−179.6 (2)
C28—B1—C10—C15	25.6 (2)	C22—C23—C24—C25	0.0 (4)
C22—B1—C10—C15	144.80 (17)	C23—C24—C25—C26	1.3 (4)
C16—B1—C10—C15	−94.6 (2)	C24—C25—C26—C27	−0.4 (4)
C28—B1—C10—C11	−162.31 (15)	C23—C22—C27—C26	3.0 (3)
C22—B1—C10—C11	−43.1 (2)	B1—C22—C27—C26	−179.58 (19)
C16—B1—C10—C11	77.51 (19)	C25—C26—C27—C22	−1.9 (4)
C15—C10—C11—C12	0.3 (3)	C10—B1—C28—C29	−153.73 (17)
B1—C10—C11—C12	−172.63 (17)	C22—B1—C28—C29	85.1 (2)
C10—C11—C12—C13	−0.7 (3)	C16—B1—C28—C29	−38.7 (2)
C11—C12—C13—C14	0.2 (3)	C10—B1—C28—C33	31.4 (2)
C12—C13—C14—C15	0.7 (3)	C22—B1—C28—C33	−89.8 (2)
C13—C14—C15—C10	−1.1 (3)	C16—B1—C28—C33	146.43 (18)
C11—C10—C15—C14	0.6 (3)	C33—C28—C29—C30	−1.8 (3)
B1—C10—C15—C14	173.11 (17)	B1—C28—C29—C30	−177.17 (18)
C28—B1—C16—C21	−37.3 (2)	C28—C29—C30—C31	−0.1 (3)
C10—B1—C16—C21	85.5 (2)	C29—C30—C31—C32	1.6 (4)
C22—B1—C16—C21	−156.69 (17)	C30—C31—C32—C33	−1.2 (4)
C28—B1—C16—C17	150.74 (18)	C31—C32—C33—C28	−0.9 (3)
C10—B1—C16—C17	−86.5 (2)	C29—C28—C33—C32	2.4 (3)
C22—B1—C16—C17	31.4 (3)	B1—C28—C33—C32	177.55 (19)
C21—C16—C17—C18	−0.1 (3)	C2—C1—N1—C5	−1.8 (3)
B1—C16—C17—C18	172.29 (19)	C2—C1—N1—C6	174.56 (17)
C16—C17—C18—C19	0.2 (3)	C4—C5—N1—C1	1.7 (3)
C17—C18—C19—C20	−0.4 (3)	C4—C5—N1—C6	−174.63 (18)
C18—C19—C20—C21	0.5 (3)	C7—C6—N1—C1	−92.6 (2)
C19—C20—C21—C16	−0.4 (3)	C7—C6—N1—C5	83.8 (2)
C17—C16—C21—C20	0.2 (3)

Symmetry code: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···N1ⁱ	0.93	2.57	2.897 (3)	101
C1—H1···Cg1	0.93	2.44	3.313 (2)	156
C4—H4···Cg3ⁱⁱ	0.93	2.63	3.280 (2)	127
C5—H5···Cg2ⁱⁱ	0.93	2.53	3.446 (2)	168

Symmetry codes: (i) −x+2, −y+2, −z+1; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₂²⁺·2C₂₄H₂₀B⁻
M_r	900.76
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.8194 (8), 10.3074 (9), 13.3980 (12)
α, β, γ (°)	97.224 (2), 92.143 (2), 111.530 (2)
V (Å³)	1246.28 (19)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.40 × 0.20 × 0.06

Data collection
Diffractometer	Bruker APEX II CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9445, 4794, 3179
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.149, 1.00
No. of reflections	4794
No. of parameters	316
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: APEX2 (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.