Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032588/is2181sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032588/is2181Isup2.hkl |
CCDC reference: 657734
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
checkCIF/PLATON results
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
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.
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%.
H atoms were generated geometrically (C—H = 0.93 or 0.97 Å) and refined as riding, with Uiso(H)= 1.2Ueq(C).
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).
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.
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.
C18H18N22+·2C24H20B− | Z = 1 |
Mr = 900.76 | F(000) = 478 |
Triclinic, P1 | Dx = 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 |
Bruker APEX II CCD area-detector diffractometer | 3179 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.038 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
φ and ω scans | h = −12→8 |
9445 measured reflections | k = −12→12 |
4794 independent reflections | l = −16→16 |
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(Fo2) + (0.0666P)2] where P = (Fo2 + 2Fc2)/3 |
4794 reflections | (Δ/σ)max = 0.008 |
316 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C18H18N22+·2C24H20B− | γ = 111.530 (2)° |
Mr = 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)° |
Bruker APEX II CCD area-detector diffractometer | 3179 reflections with I > 2σ(I) |
9445 measured reflections | Rint = 0.038 |
4794 independent reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.149 | H-atom parameters not refined |
S = 1.00 | Δρmax = 0.22 e Å−3 |
4794 reflections | Δρmin = −0.18 e Å−3 |
316 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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. |
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− |
Mr | 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 |
Rint | 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 |
Δρmax, Δρmin (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.
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. |
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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).