In the triclinic crystalline phase of the title compound, C
22H
18NO
2+·CF
3O
3S
−, the mean planes of the acridine ring systems lie parallel to each other. The benzene rings are also parallel. However, the acridine system and benzene ring in each cation are inclined at an angle of 28.5 (1)°, and the acridine system and carboxyl group are at an angle of 87.8 (2)° to each other. The structure is stabilized by C—H
O and C—H
π hydrogen bonds and π–π interactions.
Supporting information
CCDC reference: 298354
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.034
- wR factor = 0.067
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H6 .. CG3 .. 3.36 Ang.
PLAT480_ALERT_4_B Long H...A H-Bond Reported H21 .. CG3 .. 3.38 Ang.
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98
PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - O27 .. 6.56 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - O28 .. 5.77 su
PLAT231_ALERT_4_C Hirshfeld Test (Solvent) S26 - C30 .. 5.47 su
PLAT412_ALERT_2_C Short Intra XH3 .. XHn H4 .. H25C .. 1.82 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C6 .. C6 .. 3.18 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5 .. CG4 .. 3.08 Ang.
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
7 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 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
6 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2003); cell refinement: CrysAlis RED (Oxford Diffraction, 2003); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).
10-Methyl-9-(2-methylphenoxycarbonyl)acridinium trifluoromethanesulfonate
top
Crystal data top
C22H18NO2+·CF3O3S− | Z = 2 |
Mr = 477.45 | F(000) = 492 |
Triclinic, P1 | Dx = 1.527 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.160 (2) Å | Cell parameters from 5975 reflections |
b = 10.558 (2) Å | θ = 3.1–25.0° |
c = 11.060 (2) Å | µ = 0.22 mm−1 |
α = 80.35 (3)° | T = 100 K |
β = 87.87 (3)° | Needle, pale yellow |
γ = 80.03 (3)° | 0.30 × 0.15 × 0.10 mm |
V = 1038.5 (4) Å3 | |
Data collection top
Kuma KM-4-CCD κ-geometry diffractometer | 2437 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.0°, θmin = 3.1° |
ω scans | h = −9→10 |
6626 measured reflections | k = −11→12 |
3564 independent reflections | l = −13→12 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.067 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0245P)2] where P = (Fo2 + 2Fc2)/3 |
3564 reflections | (Δ/σ)max < 0.001 |
300 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.31 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.1863 (2) | 0.99908 (18) | 0.03961 (19) | 0.0171 (5) | |
H1 | 0.1905 | 1.0789 | 0.0670 | 0.020* | |
C2 | 0.1941 (2) | 0.99397 (18) | −0.08144 (19) | 0.0173 (5) | |
H2 | 0.2035 | 1.0700 | −0.1388 | 0.021* | |
C3 | 0.1884 (2) | 0.87546 (18) | −0.12311 (19) | 0.0196 (5) | |
H3 | 0.1943 | 0.8730 | −0.2086 | 0.024* | |
C4 | 0.1746 (2) | 0.76458 (19) | −0.04336 (18) | 0.0184 (5) | |
H4 | 0.1700 | 0.6863 | −0.0736 | 0.022* | |
C5 | 0.1632 (2) | 0.53996 (19) | 0.37890 (19) | 0.0202 (5) | |
H5 | 0.1727 | 0.4583 | 0.3515 | 0.024* | |
C6 | 0.1566 (2) | 0.5451 (2) | 0.5011 (2) | 0.0233 (5) | |
H6 | 0.1648 | 0.4660 | 0.5578 | 0.028* | |
C7 | 0.1378 (2) | 0.66492 (19) | 0.5464 (2) | 0.0232 (5) | |
H7 | 0.1268 | 0.6667 | 0.6319 | 0.028* | |
C8 | 0.1359 (2) | 0.77690 (19) | 0.46552 (18) | 0.0197 (5) | |
H8 | 0.1258 | 0.8573 | 0.4954 | 0.024* | |
C9 | 0.1629 (2) | 0.88846 (18) | 0.25279 (18) | 0.0154 (5) | |
N10 | 0.16051 (16) | 0.65533 (14) | 0.16876 (15) | 0.0157 (4) | |
C11 | 0.1716 (2) | 0.88606 (18) | 0.12721 (18) | 0.0149 (5) | |
C12 | 0.1671 (2) | 0.76625 (18) | 0.08407 (18) | 0.0140 (5) | |
C13 | 0.1488 (2) | 0.77680 (18) | 0.33759 (18) | 0.0157 (5) | |
C14 | 0.1560 (2) | 0.65632 (18) | 0.29237 (19) | 0.0170 (5) | |
C15 | 0.1769 (2) | 1.01267 (19) | 0.29875 (17) | 0.0166 (5) | |
O16 | 0.32269 (14) | 1.01472 (12) | 0.30869 (12) | 0.0194 (3) | |
O17 | 0.07683 (15) | 1.09417 (13) | 0.32196 (13) | 0.0241 (4) | |
C18 | 0.3684 (2) | 1.12662 (18) | 0.34204 (19) | 0.0192 (5) | |
C19 | 0.3583 (2) | 1.14740 (19) | 0.46204 (19) | 0.0202 (5) | |
C20 | 0.4221 (2) | 1.25166 (19) | 0.4882 (2) | 0.0250 (5) | |
H20 | 0.4174 | 1.2705 | 0.5694 | 0.030* | |
C21 | 0.4915 (2) | 1.3270 (2) | 0.3972 (2) | 0.0260 (5) | |
H21 | 0.5342 | 1.3966 | 0.4171 | 0.031* | |
C22 | 0.4999 (2) | 1.30342 (19) | 0.2782 (2) | 0.0254 (5) | |
H22 | 0.5478 | 1.3563 | 0.2167 | 0.031* | |
C23 | 0.4377 (2) | 1.20130 (19) | 0.2490 (2) | 0.0230 (5) | |
H23 | 0.4425 | 1.1830 | 0.1676 | 0.028* | |
C24 | 0.2861 (2) | 1.06340 (19) | 0.56189 (19) | 0.0263 (5) | |
H24A | 0.3143 | 1.0790 | 0.6420 | 0.040* | |
H24B | 0.3189 | 0.9714 | 0.5552 | 0.040* | |
H24C | 0.1782 | 1.0850 | 0.5535 | 0.040* | |
C25 | 0.1626 (2) | 0.53008 (17) | 0.12404 (19) | 0.0220 (5) | |
H25A | 0.0938 | 0.4806 | 0.1734 | 0.033* | |
H25B | 0.2630 | 0.4793 | 0.1312 | 0.033* | |
H25C | 0.1323 | 0.5476 | 0.0380 | 0.033* | |
S26 | 0.23257 (6) | 0.36221 (5) | 0.84983 (5) | 0.01791 (14) | |
O27 | 0.17644 (15) | 0.31158 (12) | 0.96862 (12) | 0.0213 (3) | |
O28 | 0.21171 (15) | 0.50317 (12) | 0.82054 (12) | 0.0229 (4) | |
O29 | 0.20178 (14) | 0.29779 (12) | 0.75065 (12) | 0.0225 (4) | |
C30 | 0.4331 (2) | 0.3167 (2) | 0.8671 (2) | 0.0231 (5) | |
F31 | 0.47393 (13) | 0.18848 (11) | 0.89992 (12) | 0.0391 (4) | |
F32 | 0.48232 (13) | 0.37370 (12) | 0.95377 (11) | 0.0359 (3) | |
F33 | 0.50550 (13) | 0.35291 (12) | 0.76367 (11) | 0.0342 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0159 (11) | 0.0117 (11) | 0.0238 (13) | −0.0026 (9) | 0.0000 (9) | −0.0031 (9) |
C2 | 0.0176 (12) | 0.0149 (11) | 0.0176 (13) | −0.0023 (9) | 0.0003 (9) | 0.0024 (9) |
C3 | 0.0191 (12) | 0.0231 (12) | 0.0166 (12) | −0.0024 (10) | −0.0013 (9) | −0.0041 (10) |
C4 | 0.0173 (12) | 0.0177 (12) | 0.0211 (13) | −0.0035 (9) | −0.0015 (9) | −0.0049 (10) |
C5 | 0.0180 (12) | 0.0169 (12) | 0.0253 (14) | −0.0045 (9) | −0.0007 (10) | −0.0002 (10) |
C6 | 0.0176 (12) | 0.0238 (13) | 0.0250 (14) | −0.0037 (10) | −0.0014 (10) | 0.0062 (10) |
C7 | 0.0183 (12) | 0.0299 (13) | 0.0198 (13) | −0.0039 (10) | −0.0013 (9) | 0.0004 (10) |
C8 | 0.0180 (12) | 0.0208 (12) | 0.0200 (13) | −0.0032 (9) | −0.0010 (9) | −0.0031 (10) |
C9 | 0.0102 (11) | 0.0160 (11) | 0.0201 (13) | −0.0011 (9) | −0.0001 (9) | −0.0047 (9) |
N10 | 0.0160 (10) | 0.0115 (9) | 0.0195 (11) | −0.0028 (7) | −0.0007 (8) | −0.0021 (8) |
C11 | 0.0092 (11) | 0.0150 (11) | 0.0194 (12) | 0.0012 (8) | −0.0013 (9) | −0.0030 (9) |
C12 | 0.0091 (11) | 0.0149 (11) | 0.0172 (12) | −0.0011 (8) | −0.0009 (9) | −0.0012 (9) |
C13 | 0.0106 (11) | 0.0202 (12) | 0.0162 (12) | −0.0016 (9) | 0.0000 (9) | −0.0039 (9) |
C14 | 0.0118 (11) | 0.0194 (12) | 0.0194 (13) | −0.0035 (9) | 0.0003 (9) | −0.0013 (9) |
C15 | 0.0221 (13) | 0.0198 (12) | 0.0075 (11) | −0.0044 (10) | −0.0022 (9) | −0.0002 (9) |
O16 | 0.0170 (8) | 0.0192 (8) | 0.0245 (9) | −0.0043 (6) | 0.0002 (6) | −0.0096 (6) |
O17 | 0.0207 (9) | 0.0223 (8) | 0.0300 (9) | 0.0021 (7) | −0.0019 (7) | −0.0116 (7) |
C18 | 0.0158 (12) | 0.0183 (11) | 0.0247 (13) | −0.0016 (9) | −0.0043 (9) | −0.0076 (10) |
C19 | 0.0184 (12) | 0.0210 (12) | 0.0203 (13) | 0.0009 (9) | −0.0007 (9) | −0.0052 (10) |
C20 | 0.0233 (13) | 0.0268 (13) | 0.0253 (13) | 0.0034 (10) | −0.0052 (10) | −0.0124 (11) |
C21 | 0.0184 (13) | 0.0224 (12) | 0.0382 (15) | −0.0005 (10) | −0.0048 (11) | −0.0098 (11) |
C22 | 0.0205 (13) | 0.0203 (12) | 0.0348 (15) | −0.0030 (10) | −0.0002 (10) | −0.0029 (10) |
C23 | 0.0183 (12) | 0.0239 (13) | 0.0264 (13) | −0.0015 (10) | 0.0007 (10) | −0.0054 (10) |
C24 | 0.0294 (14) | 0.0293 (13) | 0.0206 (13) | −0.0028 (10) | −0.0009 (10) | −0.0071 (10) |
C25 | 0.0300 (13) | 0.0156 (12) | 0.0224 (13) | −0.0055 (10) | −0.0004 (10) | −0.0070 (9) |
S26 | 0.0183 (3) | 0.0150 (3) | 0.0205 (3) | −0.0030 (2) | −0.0008 (2) | −0.0026 (2) |
O27 | 0.0254 (8) | 0.0183 (8) | 0.0190 (8) | −0.0050 (6) | 0.0058 (7) | 0.0002 (6) |
O28 | 0.0325 (9) | 0.0099 (8) | 0.0246 (9) | −0.0016 (6) | −0.0002 (7) | −0.0001 (6) |
O29 | 0.0262 (9) | 0.0223 (8) | 0.0216 (8) | −0.0063 (7) | −0.0039 (7) | −0.0078 (7) |
C30 | 0.0252 (13) | 0.0225 (13) | 0.0241 (14) | −0.0079 (10) | 0.0002 (11) | −0.0071 (10) |
F31 | 0.0269 (8) | 0.0249 (8) | 0.0603 (10) | 0.0065 (6) | −0.0058 (7) | −0.0025 (7) |
F32 | 0.0293 (8) | 0.0492 (8) | 0.0337 (8) | −0.0114 (6) | −0.0092 (6) | −0.0129 (7) |
F33 | 0.0247 (7) | 0.0499 (8) | 0.0313 (8) | −0.0148 (6) | 0.0090 (6) | −0.0095 (6) |
Geometric parameters (Å, º) top
C1—C2 | 1.348 (3) | C15—O17 | 1.196 (2) |
C1—C11 | 1.428 (2) | O16—C18 | 1.427 (2) |
C1—H1 | 0.9500 | C18—C19 | 1.378 (3) |
C2—C3 | 1.414 (3) | C18—C23 | 1.392 (3) |
C2—H2 | 0.9500 | C19—C20 | 1.407 (3) |
C3—C4 | 1.364 (3) | C19—C24 | 1.504 (3) |
C3—H3 | 0.9500 | C20—C21 | 1.382 (3) |
C4—C12 | 1.411 (3) | C20—H20 | 0.9500 |
C4—H4 | 0.9500 | C21—C22 | 1.376 (3) |
C5—C6 | 1.360 (3) | C21—H21 | 0.9500 |
C5—C14 | 1.418 (3) | C22—C23 | 1.391 (3) |
C5—H5 | 0.9500 | C22—H22 | 0.9500 |
C6—C7 | 1.418 (3) | C23—H23 | 0.9500 |
C6—H6 | 0.9500 | C24—H24A | 0.9800 |
C7—C8 | 1.356 (3) | C24—H24B | 0.9800 |
C7—H7 | 0.9500 | C24—H24C | 0.9800 |
C8—C13 | 1.416 (3) | C25—H25A | 0.9800 |
C8—H8 | 0.9500 | C25—H25B | 0.9800 |
C9—C11 | 1.392 (3) | C25—H25C | 0.9800 |
C9—C13 | 1.400 (2) | S26—O29 | 1.4438 (13) |
C9—C15 | 1.511 (3) | S26—O27 | 1.4442 (13) |
N10—C14 | 1.368 (2) | S26—O28 | 1.4494 (13) |
N10—C12 | 1.380 (2) | S26—C30 | 1.825 (2) |
N10—C25 | 1.484 (2) | C30—F31 | 1.332 (2) |
C11—C12 | 1.432 (2) | C30—F33 | 1.334 (2) |
C13—C14 | 1.433 (3) | C30—F32 | 1.343 (2) |
C15—O16 | 1.348 (2) | | |
| | | |
C2—C1—C11 | 120.89 (18) | C9—C15—O17 | 126.14 (18) |
C2—C1—H1 | 119.6 | C15—O16—C18 | 119.35 (15) |
C11—C1—H1 | 119.6 | C19—C18—C23 | 123.81 (19) |
C1—C2—C3 | 119.98 (18) | C19—C18—O16 | 120.66 (17) |
C1—C2—H2 | 120.0 | C23—C18—O16 | 115.10 (18) |
C3—C2—H2 | 120.0 | C18—C19—C20 | 116.30 (19) |
C4—C3—C2 | 121.5 (2) | C18—C19—C24 | 122.96 (18) |
C4—C3—H3 | 119.2 | C20—C19—C24 | 120.74 (19) |
C2—C3—H3 | 119.2 | C21—C20—C19 | 120.8 (2) |
C3—C4—C12 | 119.97 (18) | C21—C20—H20 | 119.6 |
C3—C4—H4 | 120.0 | C19—C20—H20 | 119.6 |
C12—C4—H4 | 120.0 | C22—C21—C20 | 121.4 (2) |
C6—C5—C14 | 120.10 (19) | C22—C21—H21 | 119.3 |
C6—C5—H5 | 119.9 | C20—C21—H21 | 119.3 |
C14—C5—H5 | 119.9 | C21—C22—C23 | 119.3 (2) |
C5—C6—C7 | 122.01 (19) | C21—C22—H22 | 120.3 |
C5—C6—H6 | 119.0 | C23—C22—H22 | 120.3 |
C7—C6—H6 | 119.0 | C22—C23—C18 | 118.3 (2) |
C8—C7—C6 | 118.8 (2) | C22—C23—H23 | 120.8 |
C8—C7—H7 | 120.6 | C18—C23—H23 | 120.8 |
C6—C7—H7 | 120.6 | C19—C24—H24A | 109.5 |
C7—C8—C13 | 121.51 (19) | C19—C24—H24B | 109.5 |
C7—C8—H8 | 119.2 | H24A—C24—H24B | 109.5 |
C13—C8—H8 | 119.2 | C19—C24—H24C | 109.5 |
C11—C9—C13 | 121.52 (17) | H24A—C24—H24C | 109.5 |
C11—C9—C15 | 119.13 (16) | H24B—C24—H24C | 109.5 |
C13—C9—C15 | 119.27 (18) | N10—C25—H25A | 109.5 |
C14—N10—C12 | 122.27 (16) | N10—C25—H25B | 109.5 |
C14—N10—C25 | 118.96 (15) | H25A—C25—H25B | 109.5 |
C12—N10—C25 | 118.75 (16) | N10—C25—H25C | 109.5 |
C9—C11—C1 | 122.17 (17) | H25A—C25—H25C | 109.5 |
C9—C11—C12 | 119.15 (17) | H25B—C25—H25C | 109.5 |
C1—C11—C12 | 118.68 (18) | O29—S26—O27 | 115.28 (8) |
N10—C12—C4 | 122.19 (17) | O29—S26—O28 | 114.83 (8) |
N10—C12—C11 | 118.83 (17) | O27—S26—O28 | 114.98 (8) |
C4—C12—C11 | 118.94 (17) | O29—S26—C30 | 103.24 (9) |
C9—C13—C8 | 122.84 (18) | O27—S26—C30 | 103.17 (9) |
C9—C13—C14 | 117.96 (18) | O28—S26—C30 | 102.86 (9) |
C8—C13—C14 | 119.11 (17) | F31—C30—F33 | 107.69 (17) |
N10—C14—C5 | 121.85 (17) | F31—C30—F32 | 107.10 (17) |
N10—C14—C13 | 119.95 (17) | F33—C30—F32 | 106.79 (15) |
C5—C14—C13 | 118.17 (19) | F31—C30—S26 | 111.75 (13) |
O17—C15—O16 | 126.38 (18) | F33—C30—S26 | 112.04 (14) |
C9—C15—O16 | 107.48 (17) | F32—C30—S26 | 111.20 (14) |
| | | |
C11—C1—C2—C3 | −0.2 (3) | C6—C5—C14—C13 | 2.9 (3) |
C1—C2—C3—C4 | 0.2 (3) | C9—C13—C14—N10 | −6.8 (3) |
C2—C3—C4—C12 | −0.6 (3) | C8—C13—C14—N10 | 176.55 (17) |
C14—C5—C6—C7 | 2.0 (3) | C9—C13—C14—C5 | 171.09 (17) |
C5—C6—C7—C8 | −4.3 (3) | C8—C13—C14—C5 | −5.6 (3) |
C6—C7—C8—C13 | 1.5 (3) | C11—C9—C15—O17 | 95.4 (2) |
C13—C9—C11—C1 | −179.90 (18) | C13—C9—C15—O17 | −87.7 (2) |
C15—C9—C11—C1 | −3.1 (3) | C11—C9—C15—O16 | −84.6 (2) |
C13—C9—C11—C12 | −0.5 (3) | C13—C9—C15—O16 | 92.3 (2) |
C15—C9—C11—C12 | 176.33 (17) | O17—C15—O16—C18 | −4.5 (3) |
C2—C1—C11—C9 | −179.84 (19) | C9—C15—O16—C18 | 175.48 (15) |
C2—C1—C11—C12 | 0.7 (3) | C15—O16—C18—C19 | 77.0 (2) |
C14—N10—C12—C4 | 178.80 (18) | C15—O16—C18—C23 | −110.11 (19) |
C25—N10—C12—C4 | 0.5 (3) | C23—C18—C19—C20 | 0.5 (3) |
C14—N10—C12—C11 | 1.0 (3) | O16—C18—C19—C20 | 172.72 (17) |
C25—N10—C12—C11 | −177.33 (16) | C23—C18—C19—C24 | −178.42 (19) |
C3—C4—C12—N10 | −176.74 (17) | O16—C18—C19—C24 | −6.2 (3) |
C3—C4—C12—C11 | 1.1 (3) | C18—C19—C20—C21 | −0.5 (3) |
C9—C11—C12—N10 | −2.7 (3) | C24—C19—C20—C21 | 178.47 (19) |
C1—C11—C12—N10 | 176.79 (16) | C19—C20—C21—C22 | 0.3 (3) |
C9—C11—C12—C4 | 179.40 (18) | C20—C21—C22—C23 | −0.2 (3) |
C1—C11—C12—C4 | −1.1 (3) | C21—C22—C23—C18 | 0.2 (3) |
C11—C9—C13—C8 | −178.38 (18) | C19—C18—C23—C22 | −0.4 (3) |
C15—C9—C13—C8 | 4.8 (3) | O16—C18—C23—C22 | −172.97 (17) |
C11—C9—C13—C14 | 5.1 (3) | O29—S26—C30—F31 | −62.96 (16) |
C15—C9—C13—C14 | −171.67 (17) | O27—S26—C30—F31 | 57.41 (16) |
C7—C8—C13—C9 | −173.09 (18) | O28—S26—C30—F31 | 177.29 (14) |
C7—C8—C13—C14 | 3.4 (3) | O29—S26—C30—F33 | 57.99 (15) |
C12—N10—C14—C5 | −173.96 (17) | O27—S26—C30—F33 | 178.36 (13) |
C25—N10—C14—C5 | 4.3 (3) | O28—S26—C30—F33 | −61.75 (15) |
C12—N10—C14—C13 | 3.8 (3) | O29—S26—C30—F32 | 177.41 (13) |
C25—N10—C14—C13 | −177.87 (16) | O27—S26—C30—F32 | −62.22 (15) |
C6—C5—C14—N10 | −179.23 (18) | O28—S26—C30—F32 | 57.66 (15) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O27i | 0.95 | 2.50 | 3.247 (2) | 136 |
C2—H2···O29i | 0.95 | 2.50 | 3.435 (2) | 166 |
C4—H4···O28ii | 0.95 | 2.39 | 3.322 (2) | 165 |
C6—H6···O29 | 0.95 | 2.53 | 3.450 (3) | 163 |
C7—H7···O28 | 0.95 | 2.53 | 3.253 (3) | 133 |
C25—H25C···O28ii | 0.98 | 2.58 | 3.423 (3) | 144 |
C5—H5···Cg4iii | 0.95 | 3.08 | 3.773 (2) | 132 |
C6—H6···Cg3iv | 0.95 | 3.36 | 3.822 (2) | 112 |
C21—H21···Cg3v | 0.95 | 3.38 | 3.954 (2) | 121 |
C24—H24B···Cg4v | 0.98 | 2.87 | 3.649 (2) | 137 |
Symmetry codes: (i) x, y+1, z−1; (ii) x, y, z−1; (iii) x, y−1, z; (iv) −x, −y+1, −z+1; (v) −x+1, −y+2, −z+1. |
π–π interactions (Å, °) in (I); Cg represents the centroid of
the C1–C4/C12/C11 ring (Fig. 1) topCgI | CgJ | Cg···Cg | Dihedral angle | Interplanar distance | Offset |
2 | 2vi | 3.789 (2) | 0.0 | 3.361 (2) | 1.634 (2) |
Notes: Cg···Cg is the distance between ring centroids.
The dihedral angle is that between the planes of the rings CgI and CgJ.
The interplanar distance is the perpendicular distance of CgI from ring J.
The offset is the perpendicular distance of ring I from ring J.
Symmetry code: (vi) -x, 2-y, -z. |