In both title pyridine derivatives, (I) and (II), the cation adopts an
E configuration with respect to the C=C. In compound (I), the PF
6− anion is disordered with occupancy factors of 0.614 (7):0.386 (7). In both the compounds, the crystal packing is stabilized by C—H

F intermolecular interactions results into two-dimensional molecular sheets, which are formed by

(14) ring motifs in compound (I),

(40) ring motifs in compound (II). In addition to that, the crystal packing is further stabilized by P—F

π interactions in compound (I) and π–π in compound (II).
Supporting information
CCDC references: 1893497; 971522
Key indicators
Structure: I
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.032
- wR factor = 0.084
- Data-to-parameter ratio = 10.5
Structure: II
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.009 Å
- R factor = 0.064
- wR factor = 0.203
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Datablock: I
Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........ 6.11 Note
PLAT260_ALERT_2_C Large Average Ueq of Residue Including P1 0.109 Check
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12 ..F3 . 2.60 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 Note
C15 H16 N O
PLAT915_ALERT_3_C No Flack x Check Done: Low Friedel Pair Coverage 81 %
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 13 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ... 12 Report
PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check
PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of P1 Check
PLAT302_ALERT_4_G Anion/Solvent/Minor-Residue Disorder (Resd 2 ) 86% Note
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 140 Note
PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min). 1 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
10 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
4 ALERT type 3 Indicator that the structure quality may be low
5 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Datablock: II
Alert level C
STRVA01_ALERT_4_C Flack test results are ambiguous.
From the CIF: _refine_ls_abs_structure_Flack 0.500
From the CIF: _refine_ls_abs_structure_Flack_su 0.200
PLAT260_ALERT_2_C Large Average Ueq of Residue Including P1 0.134 Check
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00953 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 ..F6 . 2.59 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H16 ..F4 . 2.59 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H21B ..F2 . 2.64 Ang.
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 7 Note
PLAT005_ALERT_5_G No Embedded Refinement Details Found in the CIF Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical ? Check
PLAT072_ALERT_2_G SHELXL First Parameter in WGHT Unusually Large 0.11 Report
PLAT093_ALERT_1_G No s.u.'s on H-positions, Refinement Reported as mixed Check
PLAT128_ALERT_4_G Alternate Setting for Input Space Group Cc Ic Note
PLAT244_ALERT_4_G Low 'Solvent' Ueq as Compared to Neighbors of P1 Check
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety ..... C21 Check
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note
F6 P
PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 65 Note
PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2018 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
7 ALERT level C = Check. Ensure it is not caused by an omission or oversight
11 ALERT level G = General information/check it is not something unexpected
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
4 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
9 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
Please specify the role of each of the co-authors
for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
For both structures, data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
4-[(
E)-2-(4-Methoxyphenyl)ethenyl]-1-methylpyridin-1-ium
hexafluoro-
λ6-phosphane (I)
top
Crystal data top
C15H16NO+·PF6− | F(000) = 380 |
Mr = 371.26 | Dx = 1.537 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2867 reflections |
a = 6.4320 (2) Å | θ = 2.7–26.0° |
b = 9.3645 (3) Å | µ = 0.24 mm−1 |
c = 13.6070 (5) Å | T = 296 K |
β = 101.868 (2)° | Block, green |
V = 802.06 (5) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 2 | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 2867 independent reflections |
Radiation source: fine-focus sealed tube | 2606 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
ω & φ scans | θmax = 26.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→7 |
Tmin = 0.921, Tmax = 0.932 | k = −9→11 |
8106 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0459P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.02 | Δρmax = 0.15 e Å−3 |
2867 reflections | Δρmin = −0.14 e Å−3 |
273 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
140 restraints | Extinction coefficient: 0.016 (3) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), 1198 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.08 (11) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | Uiso*/Ueq | Occ. (<1) |
C1 | 0.6868 (5) | 0.3750 (4) | 0.1233 (2) | 0.0795 (9) | |
H1A | 0.7984 | 0.4199 | 0.1710 | 0.119* | |
H1B | 0.7430 | 0.3396 | 0.0679 | 0.119* | |
H1C | 0.6290 | 0.2971 | 0.1550 | 0.119* | |
C2 | 0.3506 (4) | 0.4329 (3) | 0.02002 (19) | 0.0562 (6) | |
C3 | 0.1982 (4) | 0.5355 (3) | −0.0083 (2) | 0.0638 (7) | |
H3 | 0.2204 | 0.6270 | 0.0182 | 0.077* | |
C4 | 0.0127 (4) | 0.5051 (3) | −0.07556 (19) | 0.0605 (6) | |
H4 | −0.0885 | 0.5764 | −0.0937 | 0.073* | |
C5 | −0.0260 (4) | 0.3690 (3) | −0.11688 (16) | 0.0494 (6) | |
C6 | 0.1323 (4) | 0.2680 (3) | −0.08913 (18) | 0.0559 (6) | |
H6 | 0.1122 | 0.1769 | −0.1167 | 0.067* | |
C7 | 0.3206 (4) | 0.2978 (3) | −0.0214 (2) | 0.0579 (7) | |
H7 | 0.4246 | 0.2281 | −0.0042 | 0.069* | |
C8 | −0.2243 (4) | 0.3294 (4) | −0.18350 (15) | 0.0536 (5) | |
H8 | −0.2377 | 0.2349 | −0.2049 | 0.064* | |
C9 | −0.3863 (4) | 0.4140 (3) | −0.21639 (19) | 0.0573 (6) | |
H9 | −0.3690 | 0.5098 | −0.1986 | 0.069* | |
C10 | −0.5907 (4) | 0.3729 (3) | −0.27799 (17) | 0.0500 (6) | |
C11 | −0.7440 (4) | 0.4771 (3) | −0.3090 (2) | 0.0601 (6) | |
H11 | −0.7139 | 0.5720 | −0.2915 | 0.072* | |
C12 | −0.9364 (5) | 0.4417 (3) | −0.3646 (2) | 0.0613 (7) | |
H12 | −1.0367 | 0.5131 | −0.3844 | 0.074* | |
C13 | −0.8419 (5) | 0.2036 (3) | −0.3640 (2) | 0.0593 (7) | |
H13 | −0.8759 | 0.1099 | −0.3836 | 0.071* | |
C14 | −0.6466 (5) | 0.2330 (3) | −0.3077 (2) | 0.0588 (7) | |
H14 | −0.5494 | 0.1594 | −0.2888 | 0.071* | |
C15 | −1.1961 (4) | 0.2735 (4) | −0.4540 (2) | 0.0741 (8) | |
H15A | −1.2061 | 0.1728 | −0.4675 | 0.111* | |
H15B | −1.2142 | 0.3250 | −0.5162 | 0.111* | |
H15C | −1.3048 | 0.3012 | −0.4189 | 0.111* | |
N1 | −0.9864 (3) | 0.3063 (2) | −0.39178 (14) | 0.0543 (6) | |
O1 | 0.5245 (3) | 0.4760 (2) | 0.08788 (15) | 0.0736 (6) | |
P1 | 0.74137 (10) | 0.83995 (8) | 0.65677 (4) | 0.05309 (18) | |
F1 | 0.7553 (11) | 0.7695 (5) | 0.7626 (3) | 0.1143 (17) | 0.614 (7) |
F2 | 0.5074 (6) | 0.8863 (7) | 0.6568 (4) | 0.1075 (19) | 0.614 (7) |
F3 | 0.6535 (12) | 0.6952 (7) | 0.6034 (6) | 0.0961 (19) | 0.614 (7) |
F4 | 0.7210 (13) | 0.9108 (6) | 0.5533 (3) | 0.128 (2) | 0.614 (7) |
F5 | 0.9725 (6) | 0.7933 (8) | 0.6592 (6) | 0.125 (2) | 0.614 (7) |
F6 | 0.800 (3) | 0.9748 (11) | 0.7254 (10) | 0.109 (4) | 0.614 (7) |
F1' | 0.8909 (17) | 0.7393 (7) | 0.7289 (7) | 0.112 (3) | 0.386 (7) |
F2' | 0.5512 (16) | 0.7924 (12) | 0.6982 (8) | 0.140 (4) | 0.386 (7) |
F3' | 0.705 (2) | 0.7182 (14) | 0.5738 (8) | 0.101 (3) | 0.386 (7) |
F4' | 0.5990 (17) | 0.9410 (8) | 0.5792 (9) | 0.127 (4) | 0.386 (7) |
F5' | 0.9347 (16) | 0.8884 (11) | 0.6106 (7) | 0.120 (3) | 0.386 (7) |
F6' | 0.830 (4) | 0.9820 (15) | 0.7120 (14) | 0.084 (4) | 0.386 (7) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0625 (16) | 0.083 (3) | 0.0841 (18) | −0.0033 (15) | −0.0058 (14) | 0.0087 (17) |
C2 | 0.0537 (15) | 0.0581 (17) | 0.0568 (14) | −0.0038 (12) | 0.0116 (11) | 0.0032 (12) |
C3 | 0.0628 (16) | 0.0509 (17) | 0.0749 (16) | −0.0001 (12) | 0.0080 (13) | −0.0089 (13) |
C4 | 0.0593 (15) | 0.0527 (16) | 0.0669 (14) | 0.0059 (12) | 0.0070 (12) | −0.0023 (13) |
C5 | 0.0503 (12) | 0.0519 (17) | 0.0473 (10) | −0.0017 (10) | 0.0130 (9) | 0.0013 (10) |
C6 | 0.0586 (15) | 0.0464 (14) | 0.0637 (14) | −0.0030 (12) | 0.0145 (12) | −0.0061 (12) |
C7 | 0.0516 (14) | 0.0518 (18) | 0.0697 (15) | 0.0023 (10) | 0.0114 (11) | 0.0056 (12) |
C8 | 0.0580 (12) | 0.0529 (15) | 0.0515 (11) | 0.0006 (13) | 0.0147 (10) | 0.0023 (13) |
C9 | 0.0562 (14) | 0.0503 (15) | 0.0651 (13) | −0.0013 (11) | 0.0116 (11) | 0.0012 (12) |
C10 | 0.0523 (13) | 0.0486 (19) | 0.0512 (11) | −0.0008 (10) | 0.0157 (9) | 0.0026 (10) |
C11 | 0.0652 (17) | 0.0521 (16) | 0.0623 (14) | 0.0028 (13) | 0.0113 (12) | −0.0033 (13) |
C12 | 0.0594 (16) | 0.0594 (19) | 0.0648 (15) | 0.0099 (13) | 0.0123 (13) | 0.0080 (13) |
C13 | 0.0645 (16) | 0.0513 (17) | 0.0620 (14) | −0.0023 (13) | 0.0129 (13) | −0.0010 (13) |
C14 | 0.0569 (16) | 0.0503 (17) | 0.0700 (16) | 0.0082 (12) | 0.0144 (13) | 0.0036 (13) |
C15 | 0.0552 (15) | 0.097 (2) | 0.0656 (15) | −0.0093 (15) | 0.0013 (12) | 0.0037 (16) |
N1 | 0.0497 (11) | 0.0629 (19) | 0.0507 (10) | −0.0013 (9) | 0.0112 (8) | 0.0030 (9) |
O1 | 0.0622 (11) | 0.0680 (14) | 0.0816 (12) | −0.0055 (10) | −0.0061 (9) | −0.0044 (11) |
P1 | 0.0518 (3) | 0.0467 (3) | 0.0587 (3) | 0.0013 (3) | 0.0066 (2) | −0.0026 (3) |
F1 | 0.172 (5) | 0.089 (3) | 0.079 (2) | 0.006 (3) | 0.017 (3) | 0.028 (2) |
F2 | 0.0611 (19) | 0.140 (4) | 0.113 (3) | 0.024 (2) | −0.0018 (19) | −0.038 (3) |
F3 | 0.095 (4) | 0.068 (3) | 0.116 (4) | −0.008 (2) | −0.001 (3) | −0.025 (3) |
F4 | 0.213 (6) | 0.109 (4) | 0.073 (2) | 0.015 (4) | 0.057 (3) | 0.015 (2) |
F5 | 0.063 (2) | 0.139 (5) | 0.173 (5) | 0.018 (2) | 0.019 (3) | −0.057 (4) |
F6 | 0.111 (5) | 0.091 (6) | 0.121 (6) | 0.004 (4) | 0.018 (4) | −0.057 (5) |
F1' | 0.136 (6) | 0.074 (4) | 0.099 (5) | 0.026 (4) | −0.037 (4) | 0.005 (4) |
F2' | 0.115 (6) | 0.149 (7) | 0.182 (7) | −0.035 (5) | 0.092 (5) | −0.004 (6) |
F3' | 0.116 (7) | 0.093 (6) | 0.092 (5) | −0.020 (4) | 0.018 (4) | −0.039 (4) |
F4' | 0.127 (6) | 0.080 (4) | 0.136 (7) | 0.007 (4) | −0.064 (5) | 0.017 (4) |
F5' | 0.115 (5) | 0.120 (6) | 0.146 (6) | −0.027 (4) | 0.079 (5) | −0.019 (5) |
F6' | 0.102 (7) | 0.056 (5) | 0.091 (5) | −0.021 (5) | 0.010 (5) | −0.009 (4) |
Geometric parameters (Å, º) top
C1—O1 | 1.418 (4) | C11—H11 | 0.9300 |
C1—H1A | 0.9600 | C12—N1 | 1.341 (4) |
C1—H1B | 0.9600 | C12—H12 | 0.9300 |
C1—H1C | 0.9600 | C13—N1 | 1.338 (3) |
C2—O1 | 1.357 (3) | C13—C14 | 1.358 (4) |
C2—C3 | 1.370 (4) | C13—H13 | 0.9300 |
C2—C7 | 1.382 (4) | C14—H14 | 0.9300 |
C3—C4 | 1.376 (4) | C15—N1 | 1.470 (3) |
C3—H3 | 0.9300 | C15—H15A | 0.9600 |
C4—C5 | 1.395 (4) | C15—H15B | 0.9600 |
C4—H4 | 0.9300 | C15—H15C | 0.9600 |
C5—C6 | 1.385 (4) | P1—F2' | 1.515 (6) |
C5—C8 | 1.452 (3) | P1—F4 | 1.537 (4) |
C6—C7 | 1.391 (4) | P1—F5 | 1.543 (4) |
C6—H6 | 0.9300 | P1—F1' | 1.545 (6) |
C7—H7 | 0.9300 | P1—F4' | 1.566 (6) |
C8—C9 | 1.312 (4) | P1—F2 | 1.566 (4) |
C8—H8 | 0.9300 | P1—F1 | 1.570 (4) |
C9—C10 | 1.458 (4) | P1—F6 | 1.570 (8) |
C9—H9 | 0.9300 | P1—F5' | 1.571 (6) |
C10—C11 | 1.390 (4) | P1—F6' | 1.575 (12) |
C10—C14 | 1.396 (4) | P1—F3 | 1.586 (6) |
C11—C12 | 1.352 (4) | P1—F3' | 1.588 (10) |
| | | |
O1—C1—H1A | 109.5 | F2'—P1—F1' | 91.7 (6) |
O1—C1—H1B | 109.5 | F4—P1—F1' | 140.3 (5) |
H1A—C1—H1B | 109.5 | F5—P1—F1' | 48.9 (4) |
O1—C1—H1C | 109.5 | F2'—P1—F4' | 91.4 (6) |
H1A—C1—H1C | 109.5 | F5—P1—F4' | 127.8 (6) |
H1B—C1—H1C | 109.5 | F1'—P1—F4' | 176.6 (7) |
O1—C2—C3 | 115.2 (3) | F4—P1—F2 | 88.8 (3) |
O1—C2—C7 | 125.2 (3) | F5—P1—F2 | 178.8 (4) |
C3—C2—C7 | 119.7 (2) | F1'—P1—F2 | 129.9 (5) |
C2—C3—C4 | 121.0 (3) | F4'—P1—F2 | 53.4 (5) |
C2—C3—H3 | 119.5 | F2'—P1—F1 | 55.5 (5) |
C4—C3—H3 | 119.5 | F4—P1—F1 | 178.2 (4) |
C3—C4—C5 | 121.0 (3) | F5—P1—F1 | 89.4 (4) |
C3—C4—H4 | 119.5 | F4'—P1—F1 | 142.0 (6) |
C5—C4—H4 | 119.5 | F2—P1—F1 | 89.4 (3) |
C6—C5—C4 | 117.0 (2) | F2'—P1—F6 | 97.4 (7) |
C6—C5—C8 | 119.9 (2) | F4—P1—F6 | 99.3 (6) |
C4—C5—C8 | 123.1 (2) | F5—P1—F6 | 95.9 (7) |
C5—C6—C7 | 122.3 (3) | F1'—P1—F6 | 94.1 (6) |
C5—C6—H6 | 118.8 | F4'—P1—F6 | 87.2 (7) |
C7—C6—H6 | 118.8 | F2—P1—F6 | 83.7 (6) |
C2—C7—C6 | 118.9 (2) | F1—P1—F6 | 80.3 (6) |
C2—C7—H7 | 120.5 | F2'—P1—F5' | 178.3 (5) |
C6—C7—H7 | 120.5 | F4—P1—F5' | 55.6 (4) |
C9—C8—C5 | 126.3 (3) | F1'—P1—F5' | 89.4 (5) |
C9—C8—H8 | 116.8 | F4'—P1—F5' | 87.5 (6) |
C5—C8—H8 | 116.8 | F2—P1—F5' | 139.4 (5) |
C8—C9—C10 | 126.5 (3) | F1—P1—F5' | 126.0 (5) |
C8—C9—H9 | 116.7 | F6—P1—F5' | 83.8 (6) |
C10—C9—H9 | 116.7 | F2'—P1—F6' | 108.1 (9) |
C11—C10—C14 | 116.5 (2) | F4—P1—F6' | 91.5 (7) |
C11—C10—C9 | 119.2 (2) | F5—P1—F6' | 88.7 (10) |
C14—C10—C9 | 124.2 (2) | F1'—P1—F6' | 95.5 (8) |
C12—C11—C10 | 120.5 (3) | F4'—P1—F6' | 85.1 (8) |
C12—C11—H11 | 119.7 | F2—P1—F6' | 91.0 (9) |
C10—C11—H11 | 119.7 | F1—P1—F6' | 88.3 (7) |
N1—C12—C11 | 121.7 (3) | F5'—P1—F6' | 73.1 (9) |
N1—C12—H12 | 119.1 | F2'—P1—F3 | 71.4 (4) |
C11—C12—H12 | 119.1 | F4—P1—F3 | 89.7 (3) |
N1—C13—C14 | 121.5 (3) | F5—P1—F3 | 91.1 (3) |
N1—C13—H13 | 119.3 | F1'—P1—F3 | 83.5 (4) |
C14—C13—H13 | 119.3 | F4'—P1—F3 | 96.0 (4) |
C13—C14—C10 | 120.4 (3) | F2—P1—F3 | 89.1 (3) |
C13—C14—H14 | 119.8 | F1—P1—F3 | 90.5 (3) |
C10—C14—H14 | 119.8 | F6—P1—F3 | 168.4 (6) |
N1—C15—H15A | 109.5 | F5'—P1—F3 | 107.5 (4) |
N1—C15—H15B | 109.5 | F6'—P1—F3 | 178.8 (8) |
H15A—C15—H15B | 109.5 | F2'—P1—F3' | 92.4 (5) |
N1—C15—H15C | 109.5 | F4—P1—F3' | 71.7 (5) |
H15A—C15—H15C | 109.5 | F5—P1—F3' | 79.2 (5) |
H15B—C15—H15C | 109.5 | F1'—P1—F3' | 89.7 (6) |
C13—N1—C12 | 119.3 (2) | F4'—P1—F3' | 88.5 (7) |
C13—N1—C15 | 121.0 (3) | F2—P1—F3' | 101.4 (5) |
C12—N1—C15 | 119.8 (2) | F1—P1—F3' | 108.9 (5) |
C2—O1—C1 | 118.6 (3) | F6—P1—F3' | 169.4 (7) |
F2'—P1—F4 | 123.0 (5) | F5'—P1—F3' | 86.3 (5) |
F2'—P1—F5 | 139.2 (6) | F6'—P1—F3' | 158.7 (9) |
F4—P1—F5 | 92.4 (4) | | |
| | | |
O1—C2—C3—C4 | −179.0 (2) | C8—C9—C10—C14 | 2.9 (4) |
C7—C2—C3—C4 | 1.8 (4) | C14—C10—C11—C12 | 0.4 (4) |
C2—C3—C4—C5 | 0.0 (4) | C9—C10—C11—C12 | −178.7 (2) |
C3—C4—C5—C6 | −1.6 (4) | C10—C11—C12—N1 | −0.1 (4) |
C3—C4—C5—C8 | 176.3 (2) | N1—C13—C14—C10 | −0.6 (4) |
C4—C5—C6—C7 | 1.5 (4) | C11—C10—C14—C13 | 0.0 (4) |
C8—C5—C6—C7 | −176.5 (2) | C9—C10—C14—C13 | 179.0 (2) |
O1—C2—C7—C6 | 179.0 (2) | C14—C13—N1—C12 | 0.9 (4) |
C3—C2—C7—C6 | −1.9 (4) | C14—C13—N1—C15 | 179.1 (3) |
C5—C6—C7—C2 | 0.2 (4) | C11—C12—N1—C13 | −0.5 (4) |
C6—C5—C8—C9 | −179.4 (2) | C11—C12—N1—C15 | −178.7 (2) |
C4—C5—C8—C9 | 2.8 (4) | C3—C2—O1—C1 | 178.2 (3) |
C5—C8—C9—C10 | −175.8 (2) | C7—C2—O1—C1 | −2.7 (4) |
C8—C9—C10—C11 | −178.1 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1C···F2′i | 0.96 | 2.51 | 3.220 (8) | 131 |
C12—H12···F3ii | 0.93 | 2.60 | 3.509 (8) | 165 |
C12—H12···F3′ii | 0.93 | 2.53 | 3.454 (16) | 176 |
C13—H13···F5′iii | 0.93 | 2.40 | 3.270 (9) | 156 |
C15—H15A···F4iii | 0.96 | 2.53 | 3.443 (7) | 160 |
C15—H15B···F2iv | 0.96 | 2.46 | 3.235 (5) | 138 |
C15—H15B···F5′v | 0.96 | 2.49 | 3.162 (7) | 127 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x−2, y, z−1; (iii) x−2, y−1, z−1; (iv) −x−1, y−1/2, −z; (v) −x, y−1/2, −z. |
4-{(
E)-2-[4-(Dimethylamino)phenyl]ethenyl}-1-phenyl-1
λ5-pyridin-\
1-ylium hexafluoro-
λ6-phosphane (II)
top
Crystal data top
C21H21N2+·PF6− | F(000) = 920 |
Mr = 446.37 | Dx = 1.463 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 3926 reflections |
a = 19.4596 (14) Å | θ = 2.3–26.0° |
b = 10.7416 (8) Å | µ = 0.20 mm−1 |
c = 11.9654 (9) Å | T = 296 K |
β = 125.864 (2)° | Block, yellow |
V = 2026.9 (3) Å3 | 0.35 × 0.30 × 0.30 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 3926 independent reflections |
Radiation source: fine-focus sealed tube | 2895 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ & ω scans | θmax = 26.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −23→23 |
Tmin = 0.933, Tmax = 0.943 | k = −13→13 |
13796 measured reflections | l = −14→14 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.1113P)2 + 2.2166P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3926 reflections | Δρmax = 0.49 e Å−3 |
255 parameters | Δρmin = −0.41 e Å−3 |
65 restraints | Absolute structure: Flack (1983), 1927 Fridel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.5 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | Uiso*/Ueq | |
C1 | 0.0124 (4) | 0.0746 (5) | 0.2218 (7) | 0.0672 (15) | |
H1 | −0.0060 | 0.0194 | 0.1495 | 0.081* | |
C2 | −0.0338 (4) | 0.0925 (6) | 0.2738 (7) | 0.0755 (18) | |
H2 | −0.0856 | 0.0520 | 0.2332 | 0.091* | |
C3 | −0.0043 (4) | 0.1701 (6) | 0.3865 (8) | 0.0776 (17) | |
H3 | −0.0345 | 0.1785 | 0.4242 | 0.093* | |
C4 | 0.0694 (4) | 0.2339 (5) | 0.4407 (7) | 0.0746 (16) | |
H4 | 0.0884 | 0.2868 | 0.5149 | 0.090* | |
C5 | 0.1166 (3) | 0.2228 (5) | 0.3898 (6) | 0.0621 (13) | |
H5 | 0.1663 | 0.2681 | 0.4274 | 0.075* | |
C6 | 0.0876 (3) | 0.1414 (5) | 0.2800 (5) | 0.0537 (12) | |
C7 | 0.1625 (3) | 0.0050 (5) | 0.2239 (5) | 0.0556 (12) | |
H7 | 0.1460 | −0.0616 | 0.2530 | 0.067* | |
C8 | 0.2108 (3) | −0.0160 (5) | 0.1788 (5) | 0.0548 (12) | |
H8 | 0.2272 | −0.0971 | 0.1778 | 0.066* | |
C9 | 0.2369 (3) | 0.0807 (5) | 0.1335 (5) | 0.0535 (12) | |
C10 | 0.2116 (3) | 0.2004 (5) | 0.1416 (5) | 0.0600 (13) | |
H10 | 0.2280 | 0.2682 | 0.1140 | 0.072* | |
C11 | 0.1632 (3) | 0.2204 (5) | 0.1894 (5) | 0.0586 (13) | |
H11 | 0.1482 | 0.3010 | 0.1957 | 0.070* | |
C12 | 0.2873 (3) | 0.0638 (5) | 0.0829 (5) | 0.0569 (12) | |
H12 | 0.3022 | 0.1343 | 0.0566 | 0.068* | |
C13 | 0.3147 (3) | −0.0474 (5) | 0.0709 (5) | 0.0560 (12) | |
H13 | 0.2995 | −0.1165 | 0.0990 | 0.067* | |
C14 | 0.3642 (3) | −0.0719 (5) | 0.0201 (5) | 0.0541 (12) | |
C15 | 0.3748 (4) | −0.1927 (5) | −0.0088 (6) | 0.0614 (13) | |
H15 | 0.3505 | −0.2577 | 0.0080 | 0.074* | |
C16 | 0.4201 (4) | −0.2204 (5) | −0.0616 (6) | 0.0656 (14) | |
H16 | 0.4237 | −0.3024 | −0.0826 | 0.079* | |
C17 | 0.4603 (3) | −0.1265 (5) | −0.0834 (6) | 0.0600 (13) | |
C18 | 0.4494 (3) | −0.0039 (5) | −0.0559 (6) | 0.0626 (13) | |
H18 | 0.4744 | 0.0610 | −0.0715 | 0.075* | |
C19 | 0.4029 (3) | 0.0225 (5) | −0.0064 (5) | 0.0591 (13) | |
H19 | 0.3967 | 0.1050 | 0.0100 | 0.071* | |
C20 | 0.5037 (5) | −0.2756 (7) | −0.1855 (8) | 0.091 (2) | |
H20A | 0.5358 | −0.3311 | −0.1083 | 0.137* | |
H20B | 0.5284 | −0.2734 | −0.2353 | 0.137* | |
H20C | 0.4462 | −0.3045 | −0.2453 | 0.137* | |
C21 | 0.5524 (4) | −0.0558 (7) | −0.1456 (7) | 0.0751 (16) | |
H21A | 0.5151 | 0.0107 | −0.2024 | 0.113* | |
H21B | 0.5792 | −0.0895 | −0.1855 | 0.113* | |
H21C | 0.5950 | −0.0244 | −0.0550 | 0.113* | |
N1 | 0.5049 (3) | −0.1511 (5) | −0.1362 (5) | 0.0724 (13) | |
N2 | 0.1375 (2) | 0.1224 (4) | 0.2273 (4) | 0.0515 (10) | |
P1 | 0.26522 (10) | −0.40739 (11) | 0.33958 (15) | 0.0597 (4) | |
F5 | 0.1834 (3) | −0.4680 (5) | 0.2131 (5) | 0.1541 (16) | |
F4 | 0.3249 (3) | −0.5071 (4) | 0.3457 (7) | 0.1356 (14) | |
F3 | 0.3451 (3) | −0.3462 (6) | 0.4685 (5) | 0.1541 (16) | |
F2 | 0.2065 (3) | −0.3017 (4) | 0.3315 (7) | 0.1356 (14) | |
F6 | 0.2762 (3) | −0.3260 (6) | 0.2444 (6) | 0.1486 (17) | |
F1 | 0.2515 (3) | −0.4916 (5) | 0.4289 (6) | 0.1486 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.054 (3) | 0.051 (3) | 0.085 (4) | 0.003 (2) | 0.034 (3) | 0.011 (3) |
C2 | 0.063 (4) | 0.061 (4) | 0.097 (5) | 0.006 (3) | 0.044 (4) | 0.024 (3) |
C3 | 0.076 (4) | 0.067 (4) | 0.104 (5) | 0.022 (3) | 0.060 (4) | 0.023 (4) |
C4 | 0.069 (4) | 0.058 (3) | 0.090 (4) | 0.019 (3) | 0.043 (3) | 0.002 (3) |
C5 | 0.054 (3) | 0.049 (3) | 0.068 (3) | 0.010 (2) | 0.028 (3) | 0.003 (2) |
C6 | 0.050 (3) | 0.042 (2) | 0.060 (3) | 0.004 (2) | 0.027 (2) | 0.009 (2) |
C7 | 0.065 (3) | 0.043 (3) | 0.051 (3) | −0.007 (2) | 0.029 (2) | 0.004 (2) |
C8 | 0.063 (3) | 0.043 (3) | 0.058 (3) | −0.007 (2) | 0.035 (2) | 0.002 (2) |
C9 | 0.052 (3) | 0.051 (3) | 0.042 (2) | −0.002 (2) | 0.019 (2) | 0.0032 (19) |
C10 | 0.059 (3) | 0.049 (3) | 0.061 (3) | −0.008 (2) | 0.029 (3) | 0.012 (2) |
C11 | 0.058 (3) | 0.043 (3) | 0.061 (3) | 0.002 (2) | 0.027 (3) | 0.007 (2) |
C12 | 0.057 (3) | 0.059 (3) | 0.048 (2) | −0.011 (2) | 0.027 (2) | 0.006 (2) |
C13 | 0.053 (3) | 0.053 (3) | 0.050 (3) | −0.006 (2) | 0.024 (2) | 0.005 (2) |
C14 | 0.046 (3) | 0.050 (3) | 0.049 (2) | −0.006 (2) | 0.018 (2) | 0.003 (2) |
C15 | 0.058 (3) | 0.044 (3) | 0.065 (3) | −0.006 (2) | 0.027 (3) | 0.001 (2) |
C16 | 0.063 (3) | 0.039 (3) | 0.074 (3) | 0.003 (2) | 0.029 (3) | 0.001 (2) |
C17 | 0.054 (3) | 0.048 (3) | 0.056 (3) | 0.002 (2) | 0.020 (2) | −0.005 (2) |
C18 | 0.062 (3) | 0.047 (3) | 0.076 (3) | −0.014 (2) | 0.039 (3) | −0.009 (2) |
C19 | 0.069 (3) | 0.042 (3) | 0.070 (3) | −0.008 (2) | 0.042 (3) | −0.009 (2) |
C20 | 0.085 (4) | 0.081 (4) | 0.096 (5) | 0.009 (4) | 0.046 (4) | −0.030 (4) |
C21 | 0.063 (3) | 0.086 (4) | 0.082 (4) | 0.003 (3) | 0.045 (3) | −0.007 (3) |
N1 | 0.067 (3) | 0.058 (3) | 0.091 (3) | −0.003 (2) | 0.046 (3) | −0.019 (2) |
N2 | 0.050 (2) | 0.040 (2) | 0.052 (2) | −0.0041 (16) | 0.0224 (19) | 0.0060 (16) |
P1 | 0.0620 (7) | 0.0432 (6) | 0.0712 (8) | 0.0011 (6) | 0.0376 (6) | 0.0017 (6) |
F5 | 0.116 (3) | 0.133 (3) | 0.129 (3) | −0.033 (2) | 0.025 (2) | −0.040 (2) |
F4 | 0.150 (3) | 0.080 (2) | 0.227 (4) | 0.0386 (19) | 0.139 (3) | 0.023 (2) |
F3 | 0.116 (3) | 0.133 (3) | 0.129 (3) | −0.033 (2) | 0.025 (2) | −0.040 (2) |
F2 | 0.150 (3) | 0.080 (2) | 0.227 (4) | 0.0386 (19) | 0.139 (3) | 0.023 (2) |
F6 | 0.159 (3) | 0.155 (3) | 0.194 (4) | 0.054 (3) | 0.138 (3) | 0.096 (3) |
F1 | 0.159 (3) | 0.155 (3) | 0.194 (4) | 0.054 (3) | 0.138 (3) | 0.096 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.375 (9) | C13—H13 | 0.9300 |
C1—C6 | 1.395 (8) | C14—C15 | 1.389 (7) |
C1—H1 | 0.9300 | C14—C19 | 1.406 (7) |
C2—C3 | 1.391 (10) | C15—C16 | 1.384 (8) |
C2—H2 | 0.9300 | C15—H15 | 0.9300 |
C3—C4 | 1.363 (9) | C16—C17 | 1.392 (8) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.372 (9) | C17—N1 | 1.366 (7) |
C4—H4 | 0.9300 | C17—C18 | 1.403 (7) |
C5—C6 | 1.393 (7) | C18—C19 | 1.371 (7) |
C5—H5 | 0.9300 | C18—H18 | 0.9300 |
C6—N2 | 1.449 (7) | C19—H19 | 0.9300 |
C7—C8 | 1.350 (7) | C20—N1 | 1.456 (8) |
C7—N2 | 1.360 (6) | C20—H20A | 0.9600 |
C7—H7 | 0.9300 | C20—H20B | 0.9600 |
C8—C9 | 1.397 (7) | C20—H20C | 0.9600 |
C8—H8 | 0.9300 | C21—N1 | 1.428 (8) |
C9—C10 | 1.401 (7) | C21—H21A | 0.9600 |
C9—C12 | 1.435 (8) | C21—H21B | 0.9600 |
C10—C11 | 1.375 (8) | C21—H21C | 0.9600 |
C10—H10 | 0.9300 | P1—F1 | 1.539 (4) |
C11—N2 | 1.353 (6) | P1—F6 | 1.547 (4) |
C11—H11 | 0.9300 | P1—F4 | 1.550 (4) |
C12—C13 | 1.348 (8) | P1—F3 | 1.555 (4) |
C12—H12 | 0.9300 | P1—F5 | 1.557 (4) |
C13—C14 | 1.433 (7) | P1—F2 | 1.574 (4) |
| | | |
C2—C1—C6 | 118.4 (6) | C15—C16—C17 | 120.5 (5) |
C2—C1—H1 | 120.8 | C15—C16—H16 | 119.8 |
C6—C1—H1 | 120.8 | C17—C16—H16 | 119.8 |
C1—C2—C3 | 121.0 (6) | N1—C17—C16 | 121.7 (5) |
C1—C2—H2 | 119.5 | N1—C17—C18 | 121.0 (5) |
C3—C2—H2 | 119.5 | C16—C17—C18 | 117.2 (5) |
C4—C3—C2 | 118.9 (6) | C19—C18—C17 | 121.6 (5) |
C4—C3—H3 | 120.5 | C19—C18—H18 | 119.2 |
C2—C3—H3 | 120.5 | C17—C18—H18 | 119.2 |
C3—C4—C5 | 122.5 (6) | C18—C19—C14 | 121.6 (5) |
C3—C4—H4 | 118.8 | C18—C19—H19 | 119.2 |
C5—C4—H4 | 118.8 | C14—C19—H19 | 119.2 |
C4—C5—C6 | 117.8 (6) | N1—C20—H20A | 109.5 |
C4—C5—H5 | 121.1 | N1—C20—H20B | 109.5 |
C6—C5—H5 | 121.1 | H20A—C20—H20B | 109.5 |
C5—C6—C1 | 121.4 (5) | N1—C20—H20C | 109.5 |
C5—C6—N2 | 119.6 (4) | H20A—C20—H20C | 109.5 |
C1—C6—N2 | 119.0 (5) | H20B—C20—H20C | 109.5 |
C8—C7—N2 | 120.8 (5) | N1—C21—H21A | 109.5 |
C8—C7—H7 | 119.6 | N1—C21—H21B | 109.5 |
N2—C7—H7 | 119.6 | H21A—C21—H21B | 109.5 |
C7—C8—C9 | 121.9 (5) | N1—C21—H21C | 109.5 |
C7—C8—H8 | 119.1 | H21A—C21—H21C | 109.5 |
C9—C8—H8 | 119.1 | H21B—C21—H21C | 109.5 |
C8—C9—C10 | 115.6 (5) | C17—N1—C21 | 120.9 (5) |
C8—C9—C12 | 124.3 (5) | C17—N1—C20 | 120.1 (6) |
C10—C9—C12 | 120.1 (5) | C21—N1—C20 | 119.0 (5) |
C11—C10—C9 | 121.8 (5) | C11—N2—C7 | 120.2 (5) |
C11—C10—H10 | 119.1 | C11—N2—C6 | 120.6 (4) |
C9—C10—H10 | 119.1 | C7—N2—C6 | 119.1 (4) |
N2—C11—C10 | 119.7 (5) | F1—P1—F6 | 177.6 (4) |
N2—C11—H11 | 120.2 | F1—P1—F4 | 89.5 (3) |
C10—C11—H11 | 120.2 | F6—P1—F4 | 90.1 (3) |
C13—C12—C9 | 124.5 (5) | F1—P1—F3 | 92.2 (3) |
C13—C12—H12 | 117.7 | F6—P1—F3 | 90.1 (3) |
C9—C12—H12 | 117.7 | F4—P1—F3 | 87.7 (3) |
C12—C13—C14 | 127.8 (5) | F1—P1—F5 | 86.3 (3) |
C12—C13—H13 | 116.1 | F6—P1—F5 | 91.4 (3) |
C14—C13—H13 | 116.1 | F4—P1—F5 | 93.9 (3) |
C15—C14—C19 | 116.1 (5) | F3—P1—F5 | 177.8 (4) |
C15—C14—C13 | 120.8 (5) | F1—P1—F2 | 92.9 (3) |
C19—C14—C13 | 123.1 (5) | F6—P1—F2 | 87.5 (3) |
C16—C15—C14 | 122.9 (5) | F4—P1—F2 | 177.5 (3) |
C16—C15—H15 | 118.6 | F3—P1—F2 | 91.4 (3) |
C14—C15—H15 | 118.6 | F5—P1—F2 | 87.1 (3) |
| | | |
C6—C1—C2—C3 | −3.3 (8) | C14—C15—C16—C17 | 2.4 (8) |
C1—C2—C3—C4 | 3.4 (9) | C15—C16—C17—N1 | −179.6 (5) |
C2—C3—C4—C5 | −1.1 (9) | C15—C16—C17—C18 | −2.9 (8) |
C3—C4—C5—C6 | −1.0 (8) | N1—C17—C18—C19 | 178.2 (5) |
C4—C5—C6—C1 | 1.0 (7) | C16—C17—C18—C19 | 1.5 (8) |
C4—C5—C6—N2 | −177.1 (5) | C17—C18—C19—C14 | 0.5 (8) |
C2—C1—C6—C5 | 1.1 (8) | C15—C14—C19—C18 | −1.0 (7) |
C2—C1—C6—N2 | 179.2 (5) | C13—C14—C19—C18 | −179.6 (5) |
N2—C7—C8—C9 | −0.2 (7) | C16—C17—N1—C21 | −173.9 (5) |
C7—C8—C9—C10 | 1.7 (7) | C18—C17—N1—C21 | 9.5 (8) |
C7—C8—C9—C12 | −179.2 (5) | C16—C17—N1—C20 | 6.8 (9) |
C8—C9—C10—C11 | −0.9 (7) | C18—C17—N1—C20 | −169.8 (6) |
C12—C9—C10—C11 | 179.9 (5) | C10—C11—N2—C7 | 2.9 (7) |
C9—C10—C11—N2 | −1.4 (8) | C10—C11—N2—C6 | 179.0 (4) |
C8—C9—C12—C13 | 1.0 (8) | C8—C7—N2—C11 | −2.1 (7) |
C10—C9—C12—C13 | −179.9 (5) | C8—C7—N2—C6 | −178.3 (4) |
C9—C12—C13—C14 | 179.2 (5) | C5—C6—N2—C11 | −53.1 (6) |
C12—C13—C14—C15 | −168.5 (5) | C1—C6—N2—C11 | 128.8 (5) |
C12—C13—C14—C19 | 10.0 (8) | C5—C6—N2—C7 | 123.1 (5) |
C19—C14—C15—C16 | −0.4 (8) | C1—C6—N2—C7 | −55.0 (6) |
C13—C14—C15—C16 | 178.1 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···F6 | 0.93 | 2.59 | 3.486 (8) | 162 |
C11—H11···F5i | 0.93 | 2.55 | 3.363 (8) | 146 |
C16—H16···F4ii | 0.93 | 2.59 | 3.289 (7) | 132 |
C21—H21B···F2iii | 0.96 | 2.64 | 3.516 (8) | 152 |
Symmetry codes: (i) x, y+1, z; (ii) x, −y−1, z−1/2; (iii) x+1/2, −y−1/2, z−1/2. |