In the title salt, 1-(4-fluorobenzyl)pyridinium 7,7,8,8-tetracyanoquinodimethanide 7,7,8,8-tetracyanoquinodimethane, C
13H
13FN
+·C
8H
4(CN)
4−·C
8H
4(CN)
4, the asymmetric unit contains one cation, one anion and a neutral molecule. Intramolecular C—H
N and intermolecular C—H
N and C—H
F hydrogen bonds and π—π stacking interactions seem to be effective in the stabilization of the crystal structure.
Supporting information
CCDC reference: 636688
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.087
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 200 Deg.
PLAT230_ALERT_2_C Hirshfeld Test Diff for C15 - C16 .. 5.01 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C26 - C28 .. 6.04 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for C35 - C36 .. 6.93 su
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C14 - C16 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C15 - C16 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C24 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C23 - C25 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C26 - C28 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C27 - C28 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C35 - C36 ... 1.42 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C35 - C37 ... 1.42 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
16 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
12 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 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
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
1-(4-fluorobenzyl)pyridinium 7,7,8,8-tetracyanoquinodimethanide
7,7,8,8-tetracyanoquinodimethane
top
Crystal data top
C13H13FN+·C12H4N4−·C12H4N4 | Z = 2 |
Mr = 610.63 | F(000) = 630 |
Triclinic, P1 | Dx = 1.325 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5476 (13) Å | Cell parameters from 1378 reflections |
b = 10.8917 (14) Å | θ = 2.6–25.7° |
c = 15.346 (2) Å | µ = 0.09 mm−1 |
α = 101.203 (2)° | T = 294 K |
β = 94.189 (2)° | Block, dark green |
γ = 100.215 (2)° | 0.20 × 0.16 × 0.12 mm |
V = 1531.1 (3) Å3 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 5336 independent reflections |
Radiation source: sealed tube | 2529 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −11→11 |
Tmin = 0.983, Tmax = 0.990 | k = −9→12 |
7803 measured reflections | l = −18→18 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3 |
5336 reflections | (Δ/σ)max < 0.001 |
425 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | Uiso*/Ueq | |
F1 | 0.25409 (16) | 0.44607 (16) | 0.11758 (11) | 0.0928 (6) | |
N1 | 0.8145 (2) | 0.2174 (2) | 0.03154 (11) | 0.0459 (5) | |
N2 | 0.8331 (2) | 0.2859 (2) | 0.25040 (13) | 0.0668 (7) | |
N3 | 0.5938 (2) | 0.5315 (2) | 0.40316 (13) | 0.0692 (7) | |
N4 | 1.2725 (3) | 0.1953 (3) | 0.72285 (15) | 0.0889 (9) | |
N5 | 1.0286 (2) | 0.4229 (2) | 0.88049 (13) | 0.0626 (7) | |
N6 | 0.4525 (2) | 0.0476 (2) | 0.13401 (14) | 0.0736 (8) | |
N7 | 0.2346 (3) | 0.3067 (2) | 0.29747 (14) | 0.0817 (8) | |
N8 | 0.9181 (3) | −0.0341 (2) | 0.59835 (14) | 0.0761 (8) | |
N9 | 0.6803 (3) | 0.2067 (2) | 0.75973 (14) | 0.0784 (8) | |
C1 | 0.3715 (3) | 0.4045 (3) | 0.0867 (2) | 0.0608 (8) | |
C2 | 0.3615 (3) | 0.3449 (3) | −0.0006 (2) | 0.0675 (9) | |
H2 | 0.2761 | 0.3305 | −0.0376 | 0.081* | |
C3 | 0.4816 (3) | 0.3062 (3) | −0.03300 (17) | 0.0589 (8) | |
H3 | 0.4771 | 0.2641 | −0.0923 | 0.071* | |
C4 | 0.6084 (3) | 0.3300 (2) | 0.02257 (17) | 0.0484 (7) | |
C5 | 0.6123 (3) | 0.3895 (3) | 0.11090 (16) | 0.0559 (8) | |
H5 | 0.6971 | 0.4044 | 0.1486 | 0.067* | |
C6 | 0.4927 (3) | 0.4275 (3) | 0.14447 (17) | 0.0599 (8) | |
H6 | 0.4951 | 0.4671 | 0.2041 | 0.072* | |
C7 | 0.7419 (3) | 0.3000 (3) | −0.01631 (15) | 0.0641 (8) | |
H7A | 0.7170 | 0.2574 | −0.0786 | 0.077* | |
H7B | 0.8084 | 0.3793 | −0.0141 | 0.077* | |
C8 | 0.9560 (3) | 0.2512 (3) | 0.05677 (14) | 0.0513 (7) | |
H8 | 1.0070 | 0.3277 | 0.0473 | 0.062* | |
C9 | 1.0254 (3) | 0.1732 (3) | 0.09638 (15) | 0.0524 (7) | |
H9 | 1.1236 | 0.1968 | 0.1131 | 0.063* | |
C10 | 0.9522 (3) | 0.0610 (3) | 0.11171 (15) | 0.0491 (7) | |
C11 | 0.8071 (3) | 0.0301 (3) | 0.08543 (16) | 0.0563 (7) | |
H11 | 0.7540 | −0.0452 | 0.0953 | 0.068* | |
C12 | 0.7403 (3) | 0.1081 (3) | 0.04523 (15) | 0.0543 (7) | |
H12 | 0.6424 | 0.0852 | 0.0271 | 0.065* | |
C13 | 1.0269 (3) | −0.0223 (3) | 0.15860 (17) | 0.0750 (9) | |
H13A | 1.0255 | 0.0034 | 0.2220 | 0.112* | |
H13B | 1.1243 | −0.0139 | 0.1451 | 0.112* | |
H13C | 0.9787 | −0.1096 | 0.1388 | 0.112* | |
C14 | 0.8132 (2) | 0.3324 (2) | 0.32015 (16) | 0.0431 (7) | |
C15 | 0.6788 (3) | 0.4696 (2) | 0.40626 (14) | 0.0450 (7) | |
C16 | 0.7854 (2) | 0.3934 (2) | 0.40635 (14) | 0.0389 (6) | |
C17 | 0.8574 (2) | 0.3776 (2) | 0.48440 (14) | 0.0348 (6) | |
C18 | 0.9645 (2) | 0.3014 (2) | 0.48149 (14) | 0.0395 (6) | |
H18 | 0.9863 | 0.2610 | 0.4264 | 0.047* | |
C19 | 1.0350 (2) | 0.2866 (2) | 0.55694 (14) | 0.0400 (6) | |
H19 | 1.1049 | 0.2368 | 0.5528 | 0.048* | |
C20 | 1.0046 (2) | 0.3459 (2) | 0.64319 (14) | 0.0376 (6) | |
C21 | 0.8979 (2) | 0.4228 (2) | 0.64632 (14) | 0.0398 (6) | |
H21 | 0.8764 | 0.4633 | 0.7015 | 0.048* | |
C22 | 0.8273 (2) | 0.4379 (2) | 0.57044 (14) | 0.0393 (6) | |
H22 | 0.7581 | 0.4884 | 0.5744 | 0.047* | |
C23 | 1.0773 (2) | 0.3288 (2) | 0.72101 (14) | 0.0422 (6) | |
C24 | 1.1859 (3) | 0.2545 (3) | 0.72027 (15) | 0.0547 (8) | |
C25 | 1.0468 (2) | 0.3826 (2) | 0.80847 (17) | 0.0461 (7) | |
C26 | 0.4435 (3) | 0.1018 (3) | 0.20434 (17) | 0.0492 (7) | |
C27 | 0.3203 (3) | 0.2456 (3) | 0.29492 (15) | 0.0531 (7) | |
C28 | 0.4257 (2) | 0.1678 (2) | 0.29137 (15) | 0.0430 (6) | |
C29 | 0.5025 (2) | 0.1537 (2) | 0.36817 (14) | 0.0380 (6) | |
C30 | 0.6072 (2) | 0.0752 (2) | 0.36351 (14) | 0.0402 (6) | |
H30 | 0.6256 | 0.0332 | 0.3080 | 0.048* | |
C31 | 0.6806 (2) | 0.0607 (2) | 0.43845 (14) | 0.0410 (6) | |
H31 | 0.7498 | 0.0101 | 0.4336 | 0.049* | |
C32 | 0.6534 (2) | 0.1219 (2) | 0.52484 (14) | 0.0381 (6) | |
C33 | 0.5485 (2) | 0.2007 (2) | 0.52952 (14) | 0.0407 (6) | |
H33 | 0.5292 | 0.2419 | 0.5850 | 0.049* | |
C34 | 0.4770 (2) | 0.2164 (2) | 0.45445 (14) | 0.0409 (6) | |
H34 | 0.4099 | 0.2690 | 0.4591 | 0.049* | |
C35 | 0.7268 (2) | 0.1048 (2) | 0.60223 (15) | 0.0416 (6) | |
C36 | 0.8330 (3) | 0.0277 (3) | 0.59921 (15) | 0.0506 (7) | |
C37 | 0.7001 (3) | 0.1621 (2) | 0.68933 (17) | 0.0493 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0578 (11) | 0.0936 (14) | 0.1417 (15) | 0.0331 (11) | 0.0258 (10) | 0.0382 (12) |
N1 | 0.0436 (13) | 0.0603 (17) | 0.0343 (12) | 0.0118 (13) | 0.0065 (10) | 0.0095 (11) |
N2 | 0.0783 (17) | 0.084 (2) | 0.0391 (13) | 0.0292 (15) | 0.0048 (13) | 0.0052 (13) |
N3 | 0.0797 (18) | 0.0694 (19) | 0.0644 (16) | 0.0377 (16) | 0.0008 (13) | 0.0103 (14) |
N4 | 0.095 (2) | 0.099 (2) | 0.0817 (18) | 0.0591 (19) | −0.0048 (15) | 0.0096 (16) |
N5 | 0.0649 (15) | 0.0800 (19) | 0.0418 (13) | 0.0187 (14) | 0.0045 (12) | 0.0062 (14) |
N6 | 0.0766 (17) | 0.091 (2) | 0.0432 (14) | 0.0076 (16) | 0.0083 (13) | −0.0018 (14) |
N7 | 0.091 (2) | 0.091 (2) | 0.0646 (16) | 0.0497 (18) | −0.0100 (14) | −0.0005 (15) |
N8 | 0.093 (2) | 0.079 (2) | 0.0673 (16) | 0.0458 (17) | 0.0029 (14) | 0.0171 (14) |
N9 | 0.0972 (19) | 0.091 (2) | 0.0392 (14) | 0.0106 (17) | 0.0089 (14) | 0.0027 (15) |
C1 | 0.0451 (18) | 0.053 (2) | 0.094 (2) | 0.0157 (17) | 0.0132 (18) | 0.0313 (19) |
C2 | 0.0435 (18) | 0.071 (2) | 0.088 (2) | 0.0060 (17) | −0.0129 (17) | 0.030 (2) |
C3 | 0.0590 (18) | 0.062 (2) | 0.0534 (17) | 0.0055 (17) | −0.0087 (15) | 0.0171 (15) |
C4 | 0.0428 (16) | 0.061 (2) | 0.0477 (16) | 0.0142 (15) | 0.0018 (13) | 0.0234 (15) |
C5 | 0.0453 (16) | 0.080 (2) | 0.0469 (17) | 0.0146 (16) | 0.0000 (13) | 0.0241 (16) |
C6 | 0.0554 (18) | 0.073 (2) | 0.0561 (17) | 0.0168 (17) | 0.0130 (15) | 0.0188 (16) |
C7 | 0.0608 (18) | 0.097 (2) | 0.0448 (16) | 0.0247 (18) | 0.0057 (14) | 0.0329 (17) |
C8 | 0.0437 (16) | 0.061 (2) | 0.0463 (16) | 0.0017 (16) | 0.0091 (13) | 0.0105 (15) |
C9 | 0.0414 (16) | 0.066 (2) | 0.0489 (16) | 0.0104 (16) | 0.0026 (13) | 0.0126 (16) |
C10 | 0.0547 (18) | 0.052 (2) | 0.0402 (15) | 0.0132 (16) | 0.0106 (13) | 0.0045 (14) |
C11 | 0.0584 (19) | 0.0432 (19) | 0.0642 (19) | 0.0035 (16) | 0.0129 (15) | 0.0077 (15) |
C12 | 0.0428 (16) | 0.060 (2) | 0.0500 (17) | 0.0003 (17) | 0.0005 (13) | −0.0027 (15) |
C13 | 0.086 (2) | 0.078 (2) | 0.073 (2) | 0.035 (2) | 0.0122 (16) | 0.0263 (18) |
C14 | 0.0490 (16) | 0.0470 (18) | 0.0351 (15) | 0.0127 (14) | 0.0012 (13) | 0.0112 (14) |
C15 | 0.0573 (18) | 0.0430 (18) | 0.0340 (14) | 0.0113 (15) | 0.0022 (13) | 0.0062 (13) |
C16 | 0.0461 (15) | 0.0385 (16) | 0.0327 (14) | 0.0122 (13) | 0.0051 (12) | 0.0053 (12) |
C17 | 0.0410 (14) | 0.0316 (15) | 0.0305 (13) | 0.0073 (13) | 0.0038 (11) | 0.0036 (12) |
C18 | 0.0472 (15) | 0.0386 (16) | 0.0333 (14) | 0.0142 (13) | 0.0064 (12) | 0.0029 (12) |
C19 | 0.0419 (15) | 0.0412 (17) | 0.0377 (14) | 0.0143 (13) | 0.0062 (12) | 0.0041 (13) |
C20 | 0.0397 (14) | 0.0372 (16) | 0.0359 (14) | 0.0076 (13) | 0.0032 (12) | 0.0082 (12) |
C21 | 0.0462 (15) | 0.0410 (17) | 0.0315 (14) | 0.0116 (14) | 0.0057 (12) | 0.0026 (12) |
C22 | 0.0447 (15) | 0.0384 (16) | 0.0376 (14) | 0.0163 (13) | 0.0062 (12) | 0.0063 (13) |
C23 | 0.0462 (15) | 0.0454 (17) | 0.0368 (15) | 0.0148 (14) | 0.0028 (12) | 0.0080 (13) |
C24 | 0.063 (2) | 0.061 (2) | 0.0423 (16) | 0.0220 (17) | 0.0000 (14) | 0.0086 (15) |
C25 | 0.0459 (16) | 0.0520 (19) | 0.0413 (16) | 0.0136 (14) | −0.0037 (14) | 0.0119 (15) |
C26 | 0.0466 (16) | 0.056 (2) | 0.0442 (17) | 0.0099 (15) | −0.0011 (14) | 0.0123 (15) |
C27 | 0.0611 (19) | 0.059 (2) | 0.0380 (15) | 0.0175 (17) | −0.0032 (14) | 0.0057 (14) |
C28 | 0.0479 (16) | 0.0468 (18) | 0.0346 (15) | 0.0124 (14) | 0.0036 (12) | 0.0069 (13) |
C29 | 0.0413 (15) | 0.0378 (16) | 0.0339 (14) | 0.0074 (13) | 0.0061 (12) | 0.0051 (12) |
C30 | 0.0493 (15) | 0.0400 (16) | 0.0311 (14) | 0.0122 (14) | 0.0069 (12) | 0.0027 (12) |
C31 | 0.0462 (15) | 0.0382 (17) | 0.0391 (14) | 0.0132 (13) | 0.0076 (12) | 0.0039 (13) |
C32 | 0.0433 (15) | 0.0344 (16) | 0.0356 (14) | 0.0044 (13) | 0.0045 (12) | 0.0080 (12) |
C33 | 0.0478 (15) | 0.0398 (17) | 0.0341 (14) | 0.0110 (14) | 0.0080 (12) | 0.0031 (12) |
C34 | 0.0440 (15) | 0.0401 (17) | 0.0390 (15) | 0.0129 (13) | 0.0069 (12) | 0.0043 (13) |
C35 | 0.0476 (16) | 0.0401 (17) | 0.0374 (15) | 0.0102 (14) | 0.0050 (12) | 0.0078 (13) |
C36 | 0.0647 (19) | 0.050 (2) | 0.0375 (15) | 0.0104 (16) | −0.0001 (14) | 0.0129 (14) |
C37 | 0.0547 (17) | 0.0496 (19) | 0.0428 (16) | 0.0057 (15) | 0.0017 (14) | 0.0128 (15) |
Geometric parameters (Å, º) top
F1—C1 | 1.364 (3) | C13—H13B | 0.9600 |
N1—C12 | 1.336 (3) | C13—H13C | 0.9600 |
N1—C8 | 1.343 (3) | C14—C16 | 1.426 (3) |
N1—C7 | 1.494 (3) | C15—C16 | 1.423 (3) |
N2—C14 | 1.136 (3) | C16—C17 | 1.392 (3) |
N3—C15 | 1.146 (3) | C17—C18 | 1.426 (3) |
N4—C24 | 1.138 (3) | C17—C22 | 1.429 (3) |
N5—C25 | 1.145 (3) | C18—C19 | 1.348 (3) |
N6—C26 | 1.142 (3) | C18—H18 | 0.9300 |
N7—C27 | 1.140 (3) | C19—C20 | 1.429 (3) |
N8—C36 | 1.143 (3) | C19—H19 | 0.9300 |
N9—C37 | 1.139 (3) | C20—C23 | 1.398 (3) |
C1—C2 | 1.359 (3) | C20—C21 | 1.427 (3) |
C1—C6 | 1.360 (3) | C21—C22 | 1.355 (3) |
C2—C3 | 1.383 (3) | C21—H21 | 0.9300 |
C2—H2 | 0.9300 | C22—H22 | 0.9300 |
C3—C4 | 1.383 (3) | C23—C24 | 1.423 (3) |
C3—H3 | 0.9300 | C23—C25 | 1.429 (3) |
C4—C5 | 1.379 (3) | C26—C28 | 1.426 (3) |
C4—C7 | 1.507 (3) | C27—C28 | 1.424 (3) |
C5—C6 | 1.382 (3) | C28—C29 | 1.391 (3) |
C5—H5 | 0.9300 | C29—C30 | 1.423 (3) |
C6—H6 | 0.9300 | C29—C34 | 1.426 (3) |
C7—H7A | 0.9700 | C30—C31 | 1.353 (3) |
C7—H7B | 0.9700 | C30—H30 | 0.9300 |
C8—C9 | 1.368 (3) | C31—C32 | 1.428 (3) |
C8—H8 | 0.9300 | C31—H31 | 0.9300 |
C9—C10 | 1.368 (3) | C32—C35 | 1.395 (3) |
C9—H9 | 0.9300 | C32—C33 | 1.426 (3) |
C10—C11 | 1.377 (3) | C33—C34 | 1.351 (3) |
C10—C13 | 1.502 (3) | C33—H33 | 0.9300 |
C11—C12 | 1.359 (3) | C34—H34 | 0.9300 |
C11—H11 | 0.9300 | C35—C37 | 1.422 (3) |
C12—H12 | 0.9300 | C35—C36 | 1.424 (3) |
C13—H13A | 0.9600 | | |
| | | |
C12—N1—C8 | 120.5 (2) | C15—C16—C14 | 115.21 (19) |
C12—N1—C7 | 120.1 (2) | C16—C17—C18 | 121.2 (2) |
C8—N1—C7 | 119.4 (2) | C16—C17—C22 | 121.3 (2) |
C2—C1—C6 | 123.7 (3) | C18—C17—C22 | 117.47 (18) |
C2—C1—F1 | 118.1 (3) | C19—C18—C17 | 121.4 (2) |
C6—C1—F1 | 118.2 (3) | C19—C18—H18 | 119.3 |
C1—C2—C3 | 118.3 (3) | C17—C18—H18 | 119.3 |
C1—C2—H2 | 120.8 | C18—C19—C20 | 121.4 (2) |
C3—C2—H2 | 120.8 | C18—C19—H19 | 119.3 |
C4—C3—C2 | 120.1 (3) | C20—C19—H19 | 119.3 |
C4—C3—H3 | 119.9 | C23—C20—C21 | 121.7 (2) |
C2—C3—H3 | 119.9 | C23—C20—C19 | 120.9 (2) |
C5—C4—C3 | 119.2 (2) | C21—C20—C19 | 117.37 (19) |
C5—C4—C7 | 121.3 (2) | C22—C21—C20 | 121.2 (2) |
C3—C4—C7 | 119.3 (2) | C22—C21—H21 | 119.4 |
C4—C5—C6 | 121.3 (2) | C20—C21—H21 | 119.4 |
C4—C5—H5 | 119.4 | C21—C22—C17 | 121.2 (2) |
C6—C5—H5 | 119.4 | C21—C22—H22 | 119.4 |
C1—C6—C5 | 117.3 (3) | C17—C22—H22 | 119.4 |
C1—C6—H6 | 121.4 | C20—C23—C24 | 123.2 (2) |
C5—C6—H6 | 121.4 | C20—C23—C25 | 122.7 (2) |
N1—C7—C4 | 113.20 (19) | C24—C23—C25 | 114.13 (19) |
N1—C7—H7A | 108.9 | N4—C24—C23 | 177.6 (3) |
C4—C7—H7A | 108.9 | N5—C25—C23 | 176.0 (2) |
N1—C7—H7B | 108.9 | N6—C26—C28 | 177.5 (3) |
C4—C7—H7B | 108.9 | N7—C27—C28 | 179.1 (3) |
H7A—C7—H7B | 107.8 | C29—C28—C27 | 122.0 (2) |
N1—C8—C9 | 120.0 (2) | C29—C28—C26 | 122.3 (2) |
N1—C8—H8 | 120.0 | C27—C28—C26 | 115.6 (2) |
C9—C8—H8 | 120.0 | C28—C29—C30 | 121.3 (2) |
C10—C9—C8 | 120.9 (2) | C28—C29—C34 | 120.8 (2) |
C10—C9—H9 | 119.6 | C30—C29—C34 | 117.85 (19) |
C8—C9—H9 | 119.6 | C31—C30—C29 | 121.2 (2) |
C9—C10—C11 | 117.4 (2) | C31—C30—H30 | 119.4 |
C9—C10—C13 | 121.0 (2) | C29—C30—H30 | 119.4 |
C11—C10—C13 | 121.6 (3) | C30—C31—C32 | 120.9 (2) |
C12—C11—C10 | 120.9 (3) | C30—C31—H31 | 119.5 |
C12—C11—H11 | 119.5 | C32—C31—H31 | 119.5 |
C10—C11—H11 | 119.5 | C35—C32—C33 | 121.1 (2) |
N1—C12—C11 | 120.3 (2) | C35—C32—C31 | 121.0 (2) |
N1—C12—H12 | 119.8 | C33—C32—C31 | 117.93 (19) |
C11—C12—H12 | 119.8 | C34—C33—C32 | 120.9 (2) |
C10—C13—H13A | 109.5 | C34—C33—H33 | 119.5 |
C10—C13—H13B | 109.5 | C32—C33—H33 | 119.5 |
H13A—C13—H13B | 109.5 | C33—C34—C29 | 121.2 (2) |
C10—C13—H13C | 109.5 | C33—C34—H34 | 119.4 |
H13A—C13—H13C | 109.5 | C29—C34—H34 | 119.4 |
H13B—C13—H13C | 109.5 | C32—C35—C37 | 122.4 (2) |
N2—C14—C16 | 178.0 (3) | C32—C35—C36 | 122.1 (2) |
N3—C15—C16 | 177.5 (3) | C37—C35—C36 | 115.5 (2) |
C17—C16—C15 | 123.0 (2) | N8—C36—C35 | 178.8 (3) |
C17—C16—C14 | 121.7 (2) | N9—C37—C35 | 178.7 (3) |
| | | |
C6—C1—C2—C3 | −0.5 (4) | C17—C18—C19—C20 | 0.5 (3) |
F1—C1—C2—C3 | 178.0 (2) | C18—C19—C20—C23 | 179.3 (2) |
C1—C2—C3—C4 | −1.0 (4) | C18—C19—C20—C21 | −0.8 (3) |
C2—C3—C4—C5 | 1.7 (4) | C23—C20—C21—C22 | −179.5 (2) |
C2—C3—C4—C7 | −173.4 (2) | C19—C20—C21—C22 | 0.6 (3) |
C3—C4—C5—C6 | −1.0 (4) | C20—C21—C22—C17 | −0.2 (3) |
C7—C4—C5—C6 | 174.0 (2) | C16—C17—C22—C21 | −179.7 (2) |
C2—C1—C6—C5 | 1.2 (4) | C18—C17—C22—C21 | −0.2 (3) |
F1—C1—C6—C5 | −177.3 (2) | C21—C20—C23—C24 | −178.9 (2) |
C4—C5—C6—C1 | −0.4 (4) | C19—C20—C23—C24 | 0.9 (4) |
C12—N1—C7—C4 | 52.0 (3) | C21—C20—C23—C25 | 2.3 (4) |
C8—N1—C7—C4 | −131.1 (2) | C19—C20—C23—C25 | −177.8 (2) |
C5—C4—C7—N1 | 57.8 (3) | C27—C28—C29—C30 | 179.8 (2) |
C3—C4—C7—N1 | −127.1 (2) | C26—C28—C29—C30 | 2.2 (4) |
C12—N1—C8—C9 | 0.3 (3) | C27—C28—C29—C34 | 0.7 (4) |
C7—N1—C8—C9 | −176.5 (2) | C26—C28—C29—C34 | −176.9 (2) |
N1—C8—C9—C10 | −0.7 (4) | C28—C29—C30—C31 | −179.3 (2) |
C8—C9—C10—C11 | 0.2 (4) | C34—C29—C30—C31 | −0.1 (3) |
C8—C9—C10—C13 | −177.5 (2) | C29—C30—C31—C32 | 1.2 (4) |
C9—C10—C11—C12 | 0.5 (4) | C30—C31—C32—C35 | 178.6 (2) |
C13—C10—C11—C12 | 178.2 (2) | C30—C31—C32—C33 | −1.2 (3) |
C8—N1—C12—C11 | 0.4 (3) | C35—C32—C33—C34 | −179.6 (2) |
C7—N1—C12—C11 | 177.3 (2) | C31—C32—C33—C34 | 0.3 (3) |
C10—C11—C12—N1 | −0.9 (4) | C32—C33—C34—C29 | 0.7 (3) |
C15—C16—C17—C18 | −179.4 (2) | C28—C29—C34—C33 | 178.3 (2) |
C14—C16—C17—C18 | 1.3 (3) | C30—C29—C34—C33 | −0.8 (3) |
C15—C16—C17—C22 | 0.2 (4) | C33—C32—C35—C37 | 1.3 (4) |
C14—C16—C17—C22 | −179.2 (2) | C31—C32—C35—C37 | −178.6 (2) |
C16—C17—C18—C19 | 179.5 (2) | C33—C32—C35—C36 | −179.3 (2) |
C22—C17—C18—C19 | 0.0 (3) | C31—C32—C35—C36 | 0.8 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···N2 | 0.93 | 2.62 | 3.380 (3) | 139 |
C7—H7A···N9i | 0.97 | 2.42 | 3.366 (3) | 165 |
C8—H8···F1ii | 0.93 | 2.53 | 3.190 (3) | 128 |
C12—H12···N6 | 0.93 | 2.56 | 3.177 (4) | 124 |
C12—H12···N6iii | 0.93 | 2.62 | 3.189 (3) | 120 |
Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z; (iii) −x+1, −y, −z. |