Buy article online - an online subscription or single-article purchase is required to access this article.
10-(4-Fluorophenyl)-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2
H,5
H)-dione, C
24H
28FNO
2, (I), crystallizes with two crystallographically independent molecules (which differ slightly in conformation), while 10-(4-fluorophenyl)-9-propyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2
H,5
H)-dione, C
26H
32FNO
2, (II), crystallizes with one molecule per asymmetric unit. In both structures, the central ring in the acridine moiety is in a sofa conformation, while the outer rings adopt intermediate half-chair/sofa conformations. The central pyridine ring is orthogonal to the substituted phenyl ring. In both structures, the packing of the crystal is stabilized by C—H
O intermolecular hydrogen bonds.
Supporting information
CCDC references: 169936; 169937
The title compounds were synthesized as follows. A mixture of
2,2'-ethylidenebis(5,5-dimethylcyclohexane-1,3-dione) (2 g, 6.5 mmol) and
4-fluoroaniline (0.63 ml, 6.5 mmol) for compound (I), and a mixture of
2,2'-butylidenebis(5,5-dimethylcyclohexane-1,3-dione) (2 g, 6.0 mmol) and
4-fluoroaniline (0.60 ml, 6.0 mmol) for compound (II), were taken as starting
materials. The reaction mixtures were refluxed in acetic acid (25 ml) for 7 h,
after which time they were concentrated and poured onto ice. The yellow solids
obtained were filtered and dried to afford the title compounds in yields of
1.8 g (72.3%) for (I) and 1.75 g (71.3%) for (II). The compounds were
dissolved in a mixture of chloroform and methanol (2:1). Slow evaporation of
the solvent at room temperature produced crystals of (I) and (II) suitable for
X-ray analysis.
Please provide brief details of H-atom refinement.
Data collection: SMART (Siemens, 1996) for (I); CAD-4 Software (Enraf-Nonius, 1989) for (II). Cell refinement: SAINT (Siemens, 1996) for (I); CAD-4 Software for (II). Data reduction: SAINT for (I); SDP (Frenz, 1985) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1983b, 1995).
(I) 10-(4-Fluorophenyl)-3,3,6,6,9-pentamethyl-3,4,6,7,9,10-hexahydroacridine-
1,8(2
H,5H)-dione
top
Crystal data top
C24H28FNO2 | F(000) = 1632 |
Mr = 381.47 | Dx = 1.167 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.1481 (2) Å | Cell parameters from 8324 reflections |
b = 17.3909 (1) Å | θ = 1.3–28.3° |
c = 15.8023 (3) Å | µ = 0.08 mm−1 |
β = 112.849 (1)° | T = 293 K |
V = 4342.79 (10) Å3 | Block, pale yellow |
Z = 8 | 0.48 × 0.38 × 0.28 mm |
Data collection top
Siemens SMART CCD area-detector diffractometer | 10547 independent reflections |
Radiation source: fine-focus sealed tube | 4439 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
Detector resolution: 8.33 pixels mm-1 | θmax = 28.3°, θmin = 1.3° |
ω scans | h = −22→22 |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | k = −23→20 |
Tmin = 0.963, Tmax = 0.978 | l = −20→21 |
29750 measured reflections | |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.0465P] where P = (Fo2 + 2Fc2)/3 |
10547 reflections | (Δ/σ)max = 0.001 |
505 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
C24H28FNO2 | V = 4342.79 (10) Å3 |
Mr = 381.47 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.1481 (2) Å | µ = 0.08 mm−1 |
b = 17.3909 (1) Å | T = 293 K |
c = 15.8023 (3) Å | 0.48 × 0.38 × 0.28 mm |
β = 112.849 (1)° | |
Data collection top
Siemens SMART CCD area-detector diffractometer | 10547 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 4439 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.978 | Rint = 0.075 |
29750 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.064 | 0 restraints |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.72 e Å−3 |
10547 reflections | Δρmin = −0.27 e Å−3 |
505 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 | Uiso*/Ueq | |
F1A | 0.13594 (12) | 0.48518 (11) | 0.62816 (10) | 0.1049 (6) | |
O1A | −0.04953 (16) | 0.19049 (14) | 0.05127 (15) | 0.1204 (9) | |
O2A | 0.21222 (15) | 0.32224 (12) | 0.06847 (14) | 0.1017 (8) | |
C1A | −0.0312 (2) | 0.20976 (19) | 0.1306 (2) | 0.0937 (10) | |
C2A | −0.0707 (3) | 0.1713 (2) | 0.1906 (2) | 0.1371 (17) | |
H2A1 | −0.1256 | 0.1512 | 0.1511 | 0.164* | |
H2A2 | −0.0356 | 0.1278 | 0.2212 | 0.164* | |
C3A | −0.0820 (2) | 0.2205 (2) | 0.2609 (2) | 0.0919 (10) | |
C4A | −0.00306 (19) | 0.26358 (17) | 0.31629 (18) | 0.0843 (9) | |
H4A1 | 0.0338 | 0.2300 | 0.3641 | 0.101* | |
H4A2 | −0.0179 | 0.3068 | 0.3459 | 0.101* | |
C5A | 0.25277 (15) | 0.39325 (13) | 0.33123 (15) | 0.0542 (6) | |
H5A1 | 0.2864 | 0.3538 | 0.3728 | 0.065* | |
H5A2 | 0.2410 | 0.4329 | 0.3678 | 0.065* | |
C6A | 0.30431 (15) | 0.42835 (12) | 0.28041 (15) | 0.0508 (6) | |
C7A | 0.30978 (17) | 0.36812 (13) | 0.21246 (17) | 0.0638 (7) | |
H7A1 | 0.3400 | 0.3898 | 0.1774 | 0.077* | |
H7A2 | 0.3418 | 0.3243 | 0.2463 | 0.077* | |
C8A | 0.22443 (19) | 0.34141 (14) | 0.14764 (18) | 0.0669 (7) | |
C9A | 0.06903 (19) | 0.31306 (17) | 0.11792 (17) | 0.0757 (8) | |
H9A | 0.0736 | 0.2776 | 0.0718 | 0.091* | |
N10A | 0.10945 (12) | 0.34586 (10) | 0.30430 (12) | 0.0529 (5) | |
C11A | 0.17107 (15) | 0.35877 (12) | 0.26816 (15) | 0.0489 (6) | |
C12A | 0.15673 (16) | 0.33728 (13) | 0.18143 (15) | 0.0580 (6) | |
C13A | 0.02875 (17) | 0.27178 (15) | 0.17348 (17) | 0.0693 (7) | |
C14A | 0.04458 (16) | 0.29298 (14) | 0.26059 (16) | 0.0615 (7) | |
C15A | −0.1479 (3) | 0.2855 (3) | 0.2019 (3) | 0.171 (2) | |
H15A | −0.2001 | 0.2616 | 0.1634 | 0.257* | |
H15B | −0.1244 | 0.3127 | 0.1644 | 0.257* | |
H15C | −0.1584 | 0.3210 | 0.2428 | 0.257* | |
C16A | −0.1222 (2) | 0.1842 (2) | 0.3200 (2) | 0.1227 (14) | |
H16A | −0.1725 | 0.1573 | 0.2819 | 0.184* | |
H16B | −0.1366 | 0.2233 | 0.3542 | 0.184* | |
H16C | −0.0832 | 0.1486 | 0.3617 | 0.184* | |
C17A | 0.26336 (18) | 0.50188 (13) | 0.23096 (18) | 0.0704 (7) | |
H17A | 0.2607 | 0.5388 | 0.2749 | 0.106* | |
H17B | 0.2072 | 0.4908 | 0.1877 | 0.106* | |
H17C | 0.2963 | 0.5224 | 0.1991 | 0.106* | |
C18A | 0.39378 (16) | 0.44616 (14) | 0.35001 (18) | 0.0683 (7) | |
H18A | 0.3909 | 0.4841 | 0.3928 | 0.102* | |
H18B | 0.4274 | 0.4655 | 0.3183 | 0.102* | |
H18C | 0.4191 | 0.4001 | 0.3825 | 0.102* | |
C19A | 0.11745 (14) | 0.38134 (13) | 0.39024 (14) | 0.0485 (5) | |
C20A | 0.08155 (16) | 0.45255 (13) | 0.38764 (16) | 0.0578 (6) | |
H20A | 0.0527 | 0.4768 | 0.3317 | 0.069* | |
C21A | 0.08855 (17) | 0.48780 (15) | 0.46870 (19) | 0.0686 (7) | |
H21A | 0.0649 | 0.5360 | 0.4682 | 0.082* | |
C22A | 0.13082 (18) | 0.45028 (17) | 0.54920 (17) | 0.0669 (7) | |
C23A | 0.16696 (18) | 0.38007 (17) | 0.55324 (17) | 0.0709 (7) | |
H23A | 0.1956 | 0.3560 | 0.6094 | 0.085* | |
C24A | 0.16023 (16) | 0.34540 (14) | 0.47259 (15) | 0.0588 (6) | |
H24A | 0.1847 | 0.2975 | 0.4738 | 0.071* | |
C25A | 0.0171 (2) | 0.3831 (2) | 0.0690 (2) | 0.1142 (12) | |
H25A | −0.0380 | 0.3667 | 0.0277 | 0.171* | |
H25B | 0.0452 | 0.4087 | 0.0349 | 0.171* | |
H25C | 0.0117 | 0.4178 | 0.1135 | 0.171* | |
F1B | 0.27680 (11) | 0.57834 (10) | 0.45252 (9) | 0.0968 (6) | |
O1B | 0.41827 (13) | 0.50994 (11) | 1.11475 (11) | 0.0866 (6) | |
O2B | 0.57048 (15) | 0.74826 (11) | 1.09019 (11) | 0.0950 (7) | |
C1B | 0.38697 (17) | 0.50616 (15) | 1.03059 (17) | 0.0636 (7) | |
C2B | 0.34041 (19) | 0.43501 (15) | 0.98335 (17) | 0.0740 (8) | |
H2B1 | 0.3127 | 0.4126 | 1.0206 | 0.089* | |
H2B2 | 0.3812 | 0.3979 | 0.9797 | 0.089* | |
C3B | 0.27400 (18) | 0.44897 (14) | 0.88664 (17) | 0.0667 (7) | |
C4B | 0.31815 (16) | 0.49122 (14) | 0.83246 (15) | 0.0623 (7) | |
H4B1 | 0.3558 | 0.4557 | 0.8196 | 0.075* | |
H4B2 | 0.2758 | 0.5078 | 0.7741 | 0.075* | |
C5B | 0.47969 (16) | 0.71803 (12) | 0.80993 (15) | 0.0569 (6) | |
H5B1 | 0.4333 | 0.7281 | 0.7517 | 0.068* | |
H5B2 | 0.5211 | 0.6870 | 0.7975 | 0.068* | |
C6B | 0.52057 (17) | 0.79446 (12) | 0.85185 (15) | 0.0592 (7) | |
C7B | 0.58246 (18) | 0.77902 (14) | 0.94911 (15) | 0.0678 (7) | |
H7B1 | 0.6288 | 0.7481 | 0.9471 | 0.081* | |
H7B2 | 0.6058 | 0.8275 | 0.9783 | 0.081* | |
C8B | 0.54295 (18) | 0.73831 (13) | 1.00602 (15) | 0.0650 (7) | |
C9B | 0.43613 (17) | 0.64231 (14) | 1.01983 (15) | 0.0601 (7) | |
H9B | 0.4820 | 0.6291 | 1.0783 | 0.072* | |
N10B | 0.38747 (12) | 0.61528 (10) | 0.82829 (11) | 0.0480 (5) | |
C11B | 0.44670 (15) | 0.67302 (11) | 0.87033 (14) | 0.0467 (5) | |
C12B | 0.47461 (16) | 0.68423 (12) | 0.96164 (14) | 0.0526 (6) | |
C13B | 0.39633 (15) | 0.56911 (13) | 0.97379 (14) | 0.0528 (6) | |
C14B | 0.36831 (14) | 0.56006 (12) | 0.88194 (14) | 0.0479 (5) | |
C18B | 0.5680 (2) | 0.82851 (15) | 0.79618 (17) | 0.0864 (9) | |
H18D | 0.5288 | 0.8382 | 0.7345 | 0.130* | |
H18E | 0.6104 | 0.7929 | 0.7953 | 0.130* | |
H18F | 0.5945 | 0.8759 | 0.8238 | 0.130* | |
C17B | 0.4532 (2) | 0.85122 (16) | 0.8533 (2) | 0.0985 (11) | |
H17D | 0.4135 | 0.8602 | 0.7917 | 0.148* | |
H17E | 0.4796 | 0.8989 | 0.8801 | 0.148* | |
H17F | 0.4241 | 0.8303 | 0.8891 | 0.148* | |
C16B | 0.2403 (2) | 0.37132 (17) | 0.84113 (19) | 0.0974 (11) | |
H16D | 0.2125 | 0.3452 | 0.8752 | 0.146* | |
H16E | 0.2865 | 0.3405 | 0.8405 | 0.146* | |
H16F | 0.2007 | 0.3796 | 0.7793 | 0.146* | |
C15B | 0.20056 (19) | 0.49684 (19) | 0.8898 (2) | 0.0939 (10) | |
H15D | 0.1736 | 0.4697 | 0.9239 | 0.141* | |
H15E | 0.1603 | 0.5057 | 0.8284 | 0.141* | |
H15F | 0.2216 | 0.5452 | 0.9190 | 0.141* | |
C19B | 0.35848 (14) | 0.60444 (12) | 0.72964 (13) | 0.0444 (5) | |
C20B | 0.28648 (15) | 0.64148 (14) | 0.67204 (15) | 0.0587 (6) | |
H20B | 0.2566 | 0.6727 | 0.6968 | 0.070* | |
C21B | 0.25804 (16) | 0.63282 (14) | 0.57779 (15) | 0.0632 (7) | |
H21B | 0.2095 | 0.6578 | 0.5386 | 0.076* | |
C22B | 0.30327 (17) | 0.58668 (14) | 0.54457 (14) | 0.0590 (6) | |
C23B | 0.37488 (17) | 0.54952 (14) | 0.59984 (16) | 0.0617 (7) | |
H23B | 0.4046 | 0.5187 | 0.5745 | 0.074* | |
C24B | 0.40297 (15) | 0.55817 (13) | 0.69396 (15) | 0.0541 (6) | |
H24B | 0.4515 | 0.5329 | 0.7327 | 0.065* | |
C25B | 0.3734 (2) | 0.69308 (18) | 1.0408 (2) | 0.0953 (10) | |
H25D | 0.4014 | 0.7391 | 1.0712 | 0.143* | |
H25E | 0.3518 | 0.6657 | 1.0798 | 0.143* | |
H25F | 0.3275 | 0.7064 | 0.9845 | 0.143* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.1169 (15) | 0.1396 (15) | 0.0615 (10) | −0.0050 (11) | 0.0383 (10) | −0.0366 (10) |
O1A | 0.135 (2) | 0.142 (2) | 0.0807 (15) | −0.0678 (16) | 0.0380 (15) | −0.0541 (14) |
O2A | 0.141 (2) | 0.1099 (16) | 0.0813 (14) | −0.0488 (14) | 0.0735 (15) | −0.0463 (12) |
C1A | 0.099 (3) | 0.106 (2) | 0.070 (2) | −0.0447 (19) | 0.0257 (18) | −0.0282 (18) |
C2A | 0.159 (4) | 0.144 (3) | 0.103 (3) | −0.099 (3) | 0.045 (3) | −0.034 (3) |
C3A | 0.083 (2) | 0.119 (3) | 0.081 (2) | −0.056 (2) | 0.0391 (19) | −0.031 (2) |
C4A | 0.088 (2) | 0.098 (2) | 0.0657 (18) | −0.0433 (17) | 0.0293 (16) | −0.0102 (15) |
C5A | 0.0563 (16) | 0.0584 (14) | 0.0478 (13) | −0.0097 (11) | 0.0201 (12) | −0.0057 (11) |
C6A | 0.0588 (16) | 0.0428 (12) | 0.0557 (14) | −0.0031 (10) | 0.0277 (12) | −0.0013 (10) |
C7A | 0.077 (2) | 0.0546 (15) | 0.0741 (17) | 0.0004 (12) | 0.0444 (16) | −0.0023 (13) |
C8A | 0.099 (2) | 0.0546 (15) | 0.0617 (16) | −0.0160 (14) | 0.0474 (16) | −0.0139 (13) |
C9A | 0.086 (2) | 0.094 (2) | 0.0487 (14) | −0.0264 (16) | 0.0277 (15) | −0.0183 (14) |
N10A | 0.0590 (13) | 0.0580 (12) | 0.0439 (11) | −0.0181 (9) | 0.0223 (10) | −0.0102 (9) |
C11A | 0.0584 (16) | 0.0432 (12) | 0.0460 (13) | −0.0073 (10) | 0.0212 (12) | −0.0042 (10) |
C12A | 0.0715 (18) | 0.0561 (14) | 0.0473 (14) | −0.0129 (12) | 0.0239 (13) | −0.0098 (11) |
C13A | 0.0723 (19) | 0.0778 (18) | 0.0526 (15) | −0.0292 (14) | 0.0187 (14) | −0.0161 (13) |
C14A | 0.0632 (18) | 0.0643 (15) | 0.0547 (15) | −0.0226 (12) | 0.0204 (13) | −0.0095 (12) |
C15A | 0.076 (3) | 0.273 (6) | 0.157 (4) | 0.014 (3) | 0.037 (3) | 0.052 (4) |
C16A | 0.111 (3) | 0.150 (3) | 0.100 (3) | −0.074 (3) | 0.033 (2) | 0.000 (2) |
C17A | 0.088 (2) | 0.0474 (14) | 0.0771 (18) | −0.0021 (13) | 0.0332 (16) | 0.0060 (12) |
C18A | 0.0593 (18) | 0.0695 (17) | 0.0786 (18) | −0.0120 (13) | 0.0294 (15) | 0.0049 (13) |
C19A | 0.0488 (14) | 0.0555 (14) | 0.0430 (13) | −0.0156 (11) | 0.0198 (11) | −0.0067 (11) |
C20A | 0.0604 (17) | 0.0611 (16) | 0.0510 (14) | −0.0033 (12) | 0.0207 (12) | 0.0011 (12) |
C21A | 0.070 (2) | 0.0701 (17) | 0.0712 (18) | −0.0016 (13) | 0.0336 (15) | −0.0112 (15) |
C22A | 0.0676 (19) | 0.092 (2) | 0.0433 (15) | −0.0150 (15) | 0.0241 (14) | −0.0197 (14) |
C23A | 0.075 (2) | 0.089 (2) | 0.0415 (14) | −0.0057 (15) | 0.0147 (13) | −0.0001 (13) |
C24A | 0.0673 (18) | 0.0616 (15) | 0.0463 (14) | −0.0017 (12) | 0.0208 (12) | 0.0021 (12) |
C25A | 0.105 (3) | 0.142 (3) | 0.067 (2) | −0.016 (2) | 0.0017 (19) | 0.028 (2) |
F1B | 0.1103 (14) | 0.1356 (15) | 0.0318 (8) | 0.0088 (10) | 0.0137 (8) | −0.0114 (8) |
O1B | 0.1111 (17) | 0.1052 (15) | 0.0386 (10) | −0.0094 (12) | 0.0237 (10) | 0.0162 (10) |
O2B | 0.144 (2) | 0.0862 (13) | 0.0374 (10) | −0.0312 (12) | 0.0164 (11) | −0.0117 (9) |
C1B | 0.0719 (19) | 0.0762 (18) | 0.0438 (14) | 0.0047 (14) | 0.0235 (13) | 0.0115 (13) |
C2B | 0.092 (2) | 0.0739 (18) | 0.0566 (16) | −0.0041 (15) | 0.0296 (15) | 0.0171 (14) |
C3B | 0.078 (2) | 0.0675 (17) | 0.0534 (15) | −0.0088 (14) | 0.0246 (14) | 0.0093 (12) |
C4B | 0.0757 (19) | 0.0657 (16) | 0.0450 (14) | −0.0076 (13) | 0.0229 (13) | 0.0012 (12) |
C5B | 0.0747 (18) | 0.0518 (14) | 0.0410 (13) | −0.0033 (12) | 0.0190 (12) | −0.0021 (11) |
C6B | 0.091 (2) | 0.0393 (12) | 0.0399 (12) | 0.0007 (12) | 0.0181 (13) | −0.0006 (10) |
C7B | 0.090 (2) | 0.0517 (14) | 0.0502 (15) | −0.0103 (13) | 0.0148 (14) | −0.0018 (12) |
C8B | 0.094 (2) | 0.0509 (14) | 0.0365 (13) | 0.0011 (13) | 0.0106 (13) | −0.0034 (11) |
C9B | 0.0791 (19) | 0.0675 (16) | 0.0326 (12) | 0.0049 (13) | 0.0205 (12) | −0.0020 (11) |
N10B | 0.0597 (13) | 0.0527 (11) | 0.0295 (9) | −0.0005 (9) | 0.0149 (9) | 0.0008 (8) |
C11B | 0.0604 (16) | 0.0431 (12) | 0.0352 (11) | 0.0092 (10) | 0.0173 (11) | −0.0004 (9) |
C12B | 0.0720 (17) | 0.0487 (13) | 0.0334 (12) | 0.0074 (11) | 0.0163 (11) | −0.0011 (10) |
C13B | 0.0636 (17) | 0.0578 (14) | 0.0376 (12) | 0.0067 (11) | 0.0205 (11) | 0.0050 (10) |
C14B | 0.0534 (15) | 0.0531 (13) | 0.0380 (12) | 0.0053 (10) | 0.0184 (11) | 0.0037 (10) |
C18B | 0.133 (3) | 0.0632 (17) | 0.0612 (17) | −0.0259 (16) | 0.0363 (18) | −0.0025 (13) |
C17B | 0.130 (3) | 0.0608 (18) | 0.098 (2) | 0.0314 (17) | 0.036 (2) | 0.0069 (16) |
C16B | 0.122 (3) | 0.085 (2) | 0.076 (2) | −0.0336 (18) | 0.0287 (19) | 0.0098 (16) |
C15B | 0.072 (2) | 0.115 (2) | 0.098 (2) | −0.0006 (18) | 0.0368 (19) | 0.0146 (19) |
C19B | 0.0498 (14) | 0.0487 (12) | 0.0312 (11) | 0.0006 (10) | 0.0120 (10) | −0.0019 (9) |
C20B | 0.0589 (17) | 0.0733 (16) | 0.0422 (13) | 0.0160 (12) | 0.0177 (12) | −0.0002 (12) |
C21B | 0.0594 (17) | 0.0784 (17) | 0.0414 (13) | 0.0129 (13) | 0.0084 (12) | 0.0072 (12) |
C22B | 0.0685 (18) | 0.0746 (16) | 0.0287 (12) | −0.0044 (13) | 0.0133 (12) | −0.0066 (11) |
C23B | 0.0670 (18) | 0.0733 (17) | 0.0449 (14) | 0.0083 (13) | 0.0219 (13) | −0.0144 (12) |
C24B | 0.0575 (16) | 0.0590 (14) | 0.0410 (13) | 0.0105 (11) | 0.0139 (11) | −0.0033 (11) |
C25B | 0.119 (3) | 0.103 (2) | 0.079 (2) | 0.0127 (19) | 0.055 (2) | −0.0173 (17) |
Geometric parameters (Å, º) top
F1A—C22A | 1.359 (3) | F1B—C22B | 1.353 (2) |
O1A—C1A | 1.216 (3) | O1B—C1B | 1.227 (3) |
O2A—C8A | 1.232 (3) | O2B—C8B | 1.239 (2) |
C1A—C13A | 1.462 (4) | C1B—C13B | 1.464 (3) |
C1A—C2A | 1.517 (4) | C1B—C2B | 1.504 (4) |
C2A—C3A | 1.475 (4) | C2B—C3B | 1.530 (3) |
C2A—H2A1 | 0.9700 | C2B—H2B1 | 0.9700 |
C2A—H2A2 | 0.9700 | C2B—H2B2 | 0.9700 |
C3A—C4A | 1.496 (4) | C3B—C15B | 1.526 (4) |
C3A—C16A | 1.499 (4) | C3B—C4B | 1.533 (3) |
C3A—C15A | 1.615 (6) | C3B—C16B | 1.534 (4) |
C4A—C14A | 1.504 (3) | C4B—C14B | 1.504 (3) |
C4A—H4A1 | 0.9700 | C4B—H4B1 | 0.9700 |
C4A—H4A2 | 0.9700 | C4B—H4B2 | 0.9700 |
C5A—C11A | 1.494 (3) | C5B—C11B | 1.504 (3) |
C5A—C6A | 1.533 (3) | C5B—C6B | 1.529 (3) |
C5A—H5A1 | 0.9700 | C5B—H5B1 | 0.9700 |
C5A—H5A2 | 0.9700 | C5B—H5B2 | 0.9700 |
C6A—C17A | 1.521 (3) | C6B—C7B | 1.515 (3) |
C6A—C7A | 1.529 (3) | C6B—C17B | 1.527 (4) |
C6A—C18A | 1.533 (3) | C6B—C18B | 1.530 (3) |
C7A—C8A | 1.498 (4) | C7B—C8B | 1.497 (3) |
C7A—H7A1 | 0.9700 | C7B—H7B1 | 0.9700 |
C7A—H7A2 | 0.9700 | C7B—H7B2 | 0.9700 |
C8A—C12A | 1.456 (3) | C8B—C12B | 1.453 (3) |
C9A—C13A | 1.495 (3) | C9B—C13B | 1.493 (3) |
C9A—C12A | 1.508 (3) | C9B—C12B | 1.511 (3) |
C9A—C25A | 1.529 (4) | C9B—C25B | 1.524 (4) |
C9A—H9A | 0.9800 | C9B—H9B | 0.9800 |
N10A—C11A | 1.401 (3) | N10B—C11B | 1.399 (3) |
N10A—C14A | 1.401 (3) | N10B—C14B | 1.402 (2) |
N10A—C19A | 1.449 (3) | N10B—C19B | 1.453 (2) |
C11A—C12A | 1.348 (3) | C11B—C12B | 1.346 (3) |
C13A—C14A | 1.347 (3) | C13B—C14B | 1.349 (3) |
C15A—H15A | 0.9600 | C18B—H18D | 0.9600 |
C15A—H15B | 0.9600 | C18B—H18E | 0.9600 |
C15A—H15C | 0.9600 | C18B—H18F | 0.9600 |
C16A—H16A | 0.9600 | C17B—H17D | 0.9600 |
C16A—H16B | 0.9600 | C17B—H17E | 0.9600 |
C16A—H16C | 0.9600 | C17B—H17F | 0.9600 |
C17A—H17A | 0.9600 | C16B—H16D | 0.9600 |
C17A—H17B | 0.9600 | C16B—H16E | 0.9600 |
C17A—H17C | 0.9600 | C16B—H16F | 0.9600 |
C18A—H18A | 0.9600 | C15B—H15D | 0.9600 |
C18A—H18B | 0.9600 | C15B—H15E | 0.9600 |
C18A—H18C | 0.9600 | C15B—H15F | 0.9600 |
C19A—C24A | 1.371 (3) | C19B—C24B | 1.372 (3) |
C19A—C20A | 1.377 (3) | C19B—C20B | 1.377 (3) |
C20A—C21A | 1.383 (3) | C20B—C21B | 1.384 (3) |
C20A—H20A | 0.9300 | C20B—H20B | 0.9300 |
C21A—C22A | 1.361 (4) | C21B—C22B | 1.355 (3) |
C21A—H21A | 0.9300 | C21B—H21B | 0.9300 |
C22A—C23A | 1.359 (4) | C22B—C23B | 1.362 (3) |
C23A—C24A | 1.374 (3) | C23B—C24B | 1.382 (3) |
C23A—H23A | 0.9300 | C23B—H23B | 0.9300 |
C24A—H24A | 0.9300 | C24B—H24B | 0.9300 |
C25A—H25A | 0.9600 | C25B—H25D | 0.9600 |
C25A—H25B | 0.9600 | C25B—H25E | 0.9600 |
C25A—H25C | 0.9600 | C25B—H25F | 0.9600 |
| | | |
O1A—C1A—C13A | 122.3 (3) | O1B—C1B—C13B | 121.2 (2) |
O1A—C1A—C2A | 121.6 (3) | O1B—C1B—C2B | 120.4 (2) |
C13A—C1A—C2A | 116.1 (2) | C13B—C1B—C2B | 118.3 (2) |
C3A—C2A—C1A | 115.8 (3) | C1B—C2B—C3B | 114.3 (2) |
C3A—C2A—H2A1 | 108.3 | C1B—C2B—H2B1 | 108.7 |
C1A—C2A—H2A1 | 108.3 | C3B—C2B—H2B1 | 108.7 |
C3A—C2A—H2A2 | 108.3 | C1B—C2B—H2B2 | 108.7 |
C1A—C2A—H2A2 | 108.3 | C3B—C2B—H2B2 | 108.7 |
H2A1—C2A—H2A2 | 107.4 | H2B1—C2B—H2B2 | 107.6 |
C2A—C3A—C4A | 112.2 (3) | C15B—C3B—C2B | 111.0 (2) |
C2A—C3A—C16A | 116.8 (3) | C15B—C3B—C4B | 110.4 (2) |
C4A—C3A—C16A | 112.2 (2) | C2B—C3B—C4B | 107.3 (2) |
C2A—C3A—C15A | 103.8 (3) | C15B—C3B—C16B | 109.3 (3) |
C4A—C3A—C15A | 105.0 (3) | C2B—C3B—C16B | 109.1 (2) |
C16A—C3A—C15A | 105.5 (3) | C4B—C3B—C16B | 109.8 (2) |
C3A—C4A—C14A | 113.7 (2) | C14B—C4B—C3B | 113.46 (19) |
C3A—C4A—H4A1 | 108.8 | C14B—C4B—H4B1 | 108.9 |
C14A—C4A—H4A1 | 108.8 | C3B—C4B—H4B1 | 108.9 |
C3A—C4A—H4A2 | 108.8 | C14B—C4B—H4B2 | 108.9 |
C14A—C4A—H4A2 | 108.8 | C3B—C4B—H4B2 | 108.9 |
H4A1—C4A—H4A2 | 107.7 | H4B1—C4B—H4B2 | 107.7 |
C11A—C5A—C6A | 113.11 (18) | C11B—C5B—C6B | 113.56 (17) |
C11A—C5A—H5A1 | 109.0 | C11B—C5B—H5B1 | 108.9 |
C6A—C5A—H5A1 | 109.0 | C6B—C5B—H5B1 | 108.9 |
C11A—C5A—H5A2 | 109.0 | C11B—C5B—H5B2 | 108.9 |
C6A—C5A—H5A2 | 109.0 | C6B—C5B—H5B2 | 108.9 |
H5A1—C5A—H5A2 | 107.8 | H5B1—C5B—H5B2 | 107.7 |
C17A—C6A—C7A | 110.93 (19) | C7B—C6B—C17B | 109.6 (2) |
C17A—C6A—C18A | 109.43 (19) | C7B—C6B—C5B | 107.96 (18) |
C7A—C6A—C18A | 108.98 (19) | C17B—C6B—C5B | 110.3 (2) |
C17A—C6A—C5A | 111.03 (19) | C7B—C6B—C18B | 109.4 (2) |
C7A—C6A—C5A | 107.47 (17) | C17B—C6B—C18B | 109.5 (2) |
C18A—C6A—C5A | 108.95 (18) | C5B—C6B—C18B | 110.12 (18) |
C8A—C7A—C6A | 112.5 (2) | C8B—C7B—C6B | 113.0 (2) |
C8A—C7A—H7A1 | 109.1 | C8B—C7B—H7B1 | 109.0 |
C6A—C7A—H7A1 | 109.1 | C6B—C7B—H7B1 | 109.0 |
C8A—C7A—H7A2 | 109.1 | C8B—C7B—H7B2 | 109.0 |
C6A—C7A—H7A2 | 109.1 | C6B—C7B—H7B2 | 109.0 |
H7A1—C7A—H7A2 | 107.8 | H7B1—C7B—H7B2 | 107.8 |
O2A—C8A—C12A | 120.9 (3) | O2B—C8B—C12B | 120.5 (2) |
O2A—C8A—C7A | 121.0 (2) | O2B—C8B—C7B | 120.4 (2) |
C12A—C8A—C7A | 118.1 (2) | C12B—C8B—C7B | 118.98 (19) |
C13A—C9A—C12A | 108.2 (2) | C13B—C9B—C12B | 109.86 (17) |
C13A—C9A—C25A | 111.7 (3) | C13B—C9B—C25B | 111.8 (2) |
C12A—C9A—C25A | 110.4 (2) | C12B—C9B—C25B | 111.4 (2) |
C13A—C9A—H9A | 108.9 | C13B—C9B—H9B | 107.9 |
C12A—C9A—H9A | 108.9 | C12B—C9B—H9B | 107.9 |
C25A—C9A—H9A | 108.9 | C25B—C9B—H9B | 107.9 |
C11A—N10A—C14A | 118.98 (18) | C11B—N10B—C14B | 120.13 (16) |
C11A—N10A—C19A | 120.14 (17) | C11B—N10B—C19B | 119.04 (17) |
C14A—N10A—C19A | 120.64 (17) | C14B—N10B—C19B | 119.81 (17) |
C12A—C11A—N10A | 120.1 (2) | C12B—C11B—N10B | 120.21 (19) |
C12A—C11A—C5A | 122.9 (2) | C12B—C11B—C5B | 122.7 (2) |
N10A—C11A—C5A | 116.93 (18) | N10B—C11B—C5B | 117.05 (17) |
C11A—C12A—C8A | 120.2 (2) | C11B—C12B—C8B | 119.7 (2) |
C11A—C12A—C9A | 119.7 (2) | C11B—C12B—C9B | 121.7 (2) |
C8A—C12A—C9A | 120.1 (2) | C8B—C12B—C9B | 118.65 (19) |
C14A—C13A—C1A | 120.1 (2) | C14B—C13B—C1B | 119.6 (2) |
C14A—C13A—C9A | 120.9 (2) | C14B—C13B—C9B | 121.9 (2) |
C1A—C13A—C9A | 119.0 (2) | C1B—C13B—C9B | 118.49 (19) |
C13A—C14A—N10A | 119.3 (2) | C13B—C14B—N10B | 120.1 (2) |
C13A—C14A—C4A | 124.4 (2) | C13B—C14B—C4B | 123.0 (2) |
N10A—C14A—C4A | 116.25 (19) | N10B—C14B—C4B | 116.87 (17) |
C3A—C15A—H15A | 109.5 | C6B—C18B—H18D | 109.5 |
C3A—C15A—H15B | 109.5 | C6B—C18B—H18E | 109.5 |
H15A—C15A—H15B | 109.5 | H18D—C18B—H18E | 109.5 |
C3A—C15A—H15C | 109.5 | C6B—C18B—H18F | 109.5 |
H15A—C15A—H15C | 109.5 | H18D—C18B—H18F | 109.5 |
H15B—C15A—H15C | 109.5 | H18E—C18B—H18F | 109.5 |
C3A—C16A—H16A | 109.5 | C6B—C17B—H17D | 109.5 |
C3A—C16A—H16B | 109.5 | C6B—C17B—H17E | 109.5 |
H16A—C16A—H16B | 109.5 | H17D—C17B—H17E | 109.5 |
C3A—C16A—H16C | 109.5 | C6B—C17B—H17F | 109.5 |
H16A—C16A—H16C | 109.5 | H17D—C17B—H17F | 109.5 |
H16B—C16A—H16C | 109.5 | H17E—C17B—H17F | 109.5 |
C6A—C17A—H17A | 109.5 | C3B—C16B—H16D | 109.5 |
C6A—C17A—H17B | 109.5 | C3B—C16B—H16E | 109.5 |
H17A—C17A—H17B | 109.5 | H16D—C16B—H16E | 109.5 |
C6A—C17A—H17C | 109.5 | C3B—C16B—H16F | 109.5 |
H17A—C17A—H17C | 109.5 | H16D—C16B—H16F | 109.5 |
H17B—C17A—H17C | 109.5 | H16E—C16B—H16F | 109.5 |
C6A—C18A—H18A | 109.5 | C3B—C15B—H15D | 109.5 |
C6A—C18A—H18B | 109.5 | C3B—C15B—H15E | 109.5 |
H18A—C18A—H18B | 109.5 | H15D—C15B—H15E | 109.5 |
C6A—C18A—H18C | 109.5 | C3B—C15B—H15F | 109.5 |
H18A—C18A—H18C | 109.5 | H15D—C15B—H15F | 109.5 |
H18B—C18A—H18C | 109.5 | H15E—C15B—H15F | 109.5 |
C24A—C19A—C20A | 120.4 (2) | C24B—C19B—C20B | 120.13 (19) |
C24A—C19A—N10A | 121.1 (2) | C24B—C19B—N10B | 120.26 (19) |
C20A—C19A—N10A | 118.5 (2) | C20B—C19B—N10B | 119.60 (19) |
C19A—C20A—C21A | 119.6 (2) | C19B—C20B—C21B | 120.8 (2) |
C19A—C20A—H20A | 120.2 | C19B—C20B—H20B | 119.6 |
C21A—C20A—H20A | 120.2 | C21B—C20B—H20B | 119.6 |
C22A—C21A—C20A | 118.5 (2) | C22B—C21B—C20B | 117.8 (2) |
C22A—C21A—H21A | 120.8 | C22B—C21B—H21B | 121.1 |
C20A—C21A—H21A | 120.8 | C20B—C21B—H21B | 121.1 |
F1A—C22A—C23A | 119.5 (3) | F1B—C22B—C21B | 118.4 (2) |
F1A—C22A—C21A | 117.7 (3) | F1B—C22B—C23B | 118.8 (2) |
C23A—C22A—C21A | 122.8 (2) | C21B—C22B—C23B | 122.8 (2) |
C22A—C23A—C24A | 118.6 (2) | C22B—C23B—C24B | 119.3 (2) |
C22A—C23A—H23A | 120.7 | C22B—C23B—H23B | 120.4 |
C24A—C23A—H23A | 120.7 | C24B—C23B—H23B | 120.4 |
C19A—C24A—C23A | 120.1 (2) | C19B—C24B—C23B | 119.3 (2) |
C19A—C24A—H24A | 119.9 | C19B—C24B—H24B | 120.4 |
C23A—C24A—H24A | 119.9 | C23B—C24B—H24B | 120.4 |
C9A—C25A—H25A | 109.5 | C9B—C25B—H25D | 109.5 |
C9A—C25A—H25B | 109.5 | C9B—C25B—H25E | 109.5 |
H25A—C25A—H25B | 109.5 | H25D—C25B—H25E | 109.5 |
C9A—C25A—H25C | 109.5 | C9B—C25B—H25F | 109.5 |
H25A—C25A—H25C | 109.5 | H25D—C25B—H25F | 109.5 |
H25B—C25A—H25C | 109.5 | H25E—C25B—H25F | 109.5 |
| | | |
O1A—C1A—C2A—C3A | −148.3 (4) | O1B—C1B—C2B—C3B | 154.3 (2) |
C13A—C1A—C2A—C3A | 30.8 (5) | C13B—C1B—C2B—C3B | −27.8 (3) |
C1A—C2A—C3A—C4A | −49.5 (5) | C1B—C2B—C3B—C15B | −67.5 (3) |
C1A—C2A—C3A—C16A | 179.0 (3) | C1B—C2B—C3B—C4B | 53.2 (3) |
C1A—C2A—C3A—C15A | 63.4 (4) | C1B—C2B—C3B—C16B | 172.1 (2) |
C2A—C3A—C4A—C14A | 39.4 (4) | C15B—C3B—C4B—C14B | 71.2 (3) |
C16A—C3A—C4A—C14A | 173.2 (3) | C2B—C3B—C4B—C14B | −49.9 (3) |
C15A—C3A—C4A—C14A | −72.7 (3) | C16B—C3B—C4B—C14B | −168.3 (2) |
C11A—C5A—C6A—C17A | 71.5 (2) | C11B—C5B—C6B—C7B | 49.1 (3) |
C11A—C5A—C6A—C7A | −50.0 (3) | C11B—C5B—C6B—C17B | −70.6 (3) |
C11A—C5A—C6A—C18A | −167.92 (19) | C11B—C5B—C6B—C18B | 168.5 (2) |
C17A—C6A—C7A—C8A | −65.3 (3) | C17B—C6B—C7B—C8B | 65.7 (3) |
C18A—C6A—C7A—C8A | 174.19 (19) | C5B—C6B—C7B—C8B | −54.4 (3) |
C5A—C6A—C7A—C8A | 56.3 (3) | C18B—C6B—C7B—C8B | −174.2 (2) |
C6A—C7A—C8A—O2A | 147.7 (2) | C6B—C7B—C8B—O2B | −150.6 (2) |
C6A—C7A—C8A—C12A | −33.5 (3) | C6B—C7B—C8B—C12B | 32.3 (3) |
C14A—N10A—C11A—C12A | 17.3 (3) | C14B—N10B—C11B—C12B | −11.6 (3) |
C19A—N10A—C11A—C12A | −168.4 (2) | C19B—N10B—C11B—C12B | −179.98 (19) |
C14A—N10A—C11A—C5A | −159.9 (2) | C14B—N10B—C11B—C5B | 165.59 (19) |
C19A—N10A—C11A—C5A | 14.4 (3) | C19B—N10B—C11B—C5B | −2.8 (3) |
C6A—C5A—C11A—C12A | 21.0 (3) | C6B—C5B—C11B—C12B | −21.4 (3) |
C6A—C5A—C11A—N10A | −161.89 (19) | C6B—C5B—C11B—N10B | 161.5 (2) |
N10A—C11A—C12A—C8A | −172.0 (2) | N10B—C11B—C12B—C8B | 173.1 (2) |
C5A—C11A—C12A—C8A | 5.0 (4) | C5B—C11B—C12B—C8B | −3.9 (3) |
N10A—C11A—C12A—C9A | 11.3 (3) | N10B—C11B—C12B—C9B | −7.4 (3) |
C5A—C11A—C12A—C9A | −171.7 (2) | C5B—C11B—C12B—C9B | 175.6 (2) |
O2A—C8A—C12A—C11A | −179.7 (2) | O2B—C8B—C12B—C11B | −178.6 (2) |
C7A—C8A—C12A—C11A | 1.5 (3) | C7B—C8B—C12B—C11B | −1.6 (3) |
O2A—C8A—C12A—C9A | −3.1 (4) | O2B—C8B—C12B—C9B | 1.8 (4) |
C7A—C8A—C12A—C9A | 178.1 (2) | C7B—C8B—C12B—C9B | 178.9 (2) |
C13A—C9A—C12A—C11A | −35.1 (3) | C13B—C9B—C12B—C11B | 24.4 (3) |
C25A—C9A—C12A—C11A | 87.3 (3) | C25B—C9B—C12B—C11B | −100.0 (3) |
C13A—C9A—C12A—C8A | 148.2 (2) | C13B—C9B—C12B—C8B | −156.1 (2) |
C25A—C9A—C12A—C8A | −89.3 (3) | C25B—C9B—C12B—C8B | 79.5 (3) |
O1A—C1A—C13A—C14A | 177.5 (3) | O1B—C1B—C13B—C14B | 173.6 (2) |
C2A—C1A—C13A—C14A | −1.6 (5) | C2B—C1B—C13B—C14B | −4.3 (4) |
O1A—C1A—C13A—C9A | 0.0 (5) | O1B—C1B—C13B—C9B | −7.1 (4) |
C2A—C1A—C13A—C9A | −179.1 (3) | C2B—C1B—C13B—C9B | 175.0 (2) |
C12A—C9A—C13A—C14A | 34.8 (4) | C12B—C9B—C13B—C14B | −25.6 (3) |
C25A—C9A—C13A—C14A | −86.9 (3) | C25B—C9B—C13B—C14B | 98.6 (3) |
C12A—C9A—C13A—C1A | −147.8 (3) | C12B—C9B—C13B—C1B | 155.1 (2) |
C25A—C9A—C13A—C1A | 90.6 (3) | C25B—C9B—C13B—C1B | −80.7 (3) |
C1A—C13A—C14A—N10A | 172.3 (3) | C1B—C13B—C14B—N10B | −171.0 (2) |
C9A—C13A—C14A—N10A | −10.2 (4) | C9B—C13B—C14B—N10B | 9.7 (3) |
C1A—C13A—C14A—C4A | −7.6 (5) | C1B—C13B—C14B—C4B | 7.4 (4) |
C9A—C13A—C14A—C4A | 169.8 (3) | C9B—C13B—C14B—C4B | −171.9 (2) |
C11A—N10A—C14A—C13A | −18.0 (4) | C11B—N10B—C14B—C13B | 10.5 (3) |
C19A—N10A—C14A—C13A | 167.7 (2) | C19B—N10B—C14B—C13B | 178.8 (2) |
C11A—N10A—C14A—C4A | 162.0 (2) | C11B—N10B—C14B—C4B | −167.9 (2) |
C19A—N10A—C14A—C4A | −12.3 (3) | C19B—N10B—C14B—C4B | 0.4 (3) |
C3A—C4A—C14A—C13A | −11.9 (5) | C3B—C4B—C14B—C13B | 21.6 (3) |
C3A—C4A—C14A—N10A | 168.1 (3) | C3B—C4B—C14B—N10B | −160.0 (2) |
C11A—N10A—C19A—C24A | −89.3 (3) | C11B—N10B—C19B—C24B | 86.5 (3) |
C14A—N10A—C19A—C24A | 85.0 (3) | C14B—N10B—C19B—C24B | −81.9 (3) |
C11A—N10A—C19A—C20A | 90.3 (3) | C11B—N10B—C19B—C20B | −92.8 (3) |
C14A—N10A—C19A—C20A | −95.5 (3) | C14B—N10B—C19B—C20B | 98.7 (2) |
C24A—C19A—C20A—C21A | −0.2 (4) | C24B—C19B—C20B—C21B | −0.1 (4) |
N10A—C19A—C20A—C21A | −179.8 (2) | N10B—C19B—C20B—C21B | 179.3 (2) |
C19A—C20A—C21A—C22A | −0.3 (4) | C19B—C20B—C21B—C22B | 0.2 (4) |
C20A—C21A—C22A—F1A | −179.0 (2) | C20B—C21B—C22B—F1B | −179.2 (2) |
C20A—C21A—C22A—C23A | 0.6 (4) | C20B—C21B—C22B—C23B | −0.4 (4) |
F1A—C22A—C23A—C24A | 179.3 (2) | F1B—C22B—C23B—C24B | 179.4 (2) |
C21A—C22A—C23A—C24A | −0.3 (4) | C21B—C22B—C23B—C24B | 0.6 (4) |
C20A—C19A—C24A—C23A | 0.5 (4) | C20B—C19B—C24B—C23B | 0.3 (3) |
N10A—C19A—C24A—C23A | −179.9 (2) | N10B—C19B—C24B—C23B | −179.1 (2) |
C22A—C23A—C24A—C19A | −0.3 (4) | C22B—C23B—C24B—C19B | −0.5 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H9A···O1A | 0.98 | 2.51 | 2.850 (4) | 100 |
C9A—H9A···O2A | 0.98 | 2.52 | 2.856 (5) | 100 |
C9B—H9B···O1B | 0.98 | 2.51 | 2.828 (4) | 98 |
C9B—H9B···O2B | 0.98 | 2.53 | 2.819 (3) | 97 |
C24A—H24A···O2Ai | 0.93 | 2.50 | 3.247 (3) | 138 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
(II) 10-(4-fluorophenyl)-9-propyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-
hexahydroacridine-1,8(2
H,5H)-dione
top
Crystal data top
C26H32FNO2 | F(000) = 1760 |
Mr = 409.53 | Dx = 1.184 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54180 Å |
a = 27.454 (1) Å | Cell parameters from 25 reflections |
b = 12.2738 (10) Å | θ = 12.5–18.0° |
c = 16.2792 (10) Å | µ = 0.63 mm−1 |
β = 123.118 (10)° | T = 293 K |
V = 4594.4 (5) Å3 | Block, pale yellow |
Z = 8 | 0.20 × 0.18 × 0.16 mm |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.053 |
Radiation source: fine-focus sealed tube | θmax = 72.7°, θmin = 3.9° |
Graphite monochromator | h = 0→34 |
ω/2θ scans | k = 0→15 |
4454 measured reflections | l = −20→16 |
4374 independent reflections | 3 standard reflections every 200 reflections |
3087 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.196 | w = 1/[σ2(Fo2) + (0.0504P)2 + 0.0465P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
4374 reflections | Δρmax = 0.17 e Å−3 |
272 parameters | Δρmin = −0.17 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00046 (13) |
Crystal data top
C26H32FNO2 | V = 4594.4 (5) Å3 |
Mr = 409.53 | Z = 8 |
Monoclinic, C2/c | Cu Kα radiation |
a = 27.454 (1) Å | µ = 0.63 mm−1 |
b = 12.2738 (10) Å | T = 293 K |
c = 16.2792 (10) Å | 0.20 × 0.18 × 0.16 mm |
β = 123.118 (10)° | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.053 |
4454 measured reflections | 3 standard reflections every 200 reflections |
4374 independent reflections | intensity decay: <1% |
3087 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.196 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.17 e Å−3 |
4374 reflections | Δρmin = −0.17 e Å−3 |
272 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 | Uiso*/Ueq | |
F1 | 0.00474 (8) | 0.66354 (13) | 0.14003 (19) | 0.1566 (9) | |
O1 | 0.23797 (7) | 0.02710 (13) | 0.51580 (11) | 0.0882 (5) | |
O2 | 0.25392 (7) | 0.03973 (14) | 0.23311 (11) | 0.0843 (5) | |
C1 | 0.20570 (8) | 0.10666 (16) | 0.48565 (14) | 0.0621 (5) | |
C2 | 0.19344 (9) | 0.16913 (17) | 0.55147 (14) | 0.0658 (5) | |
H2A | 0.2241 | 0.2223 | 0.5880 | 0.079* | |
H2B | 0.1942 | 0.1193 | 0.5984 | 0.079* | |
C3 | 0.13527 (9) | 0.22761 (16) | 0.49688 (14) | 0.0627 (5) | |
C4 | 0.13309 (9) | 0.29930 (15) | 0.41763 (14) | 0.0613 (5) | |
H4A | 0.0939 | 0.3273 | 0.3750 | 0.074* | |
H4B | 0.1589 | 0.3610 | 0.4490 | 0.074* | |
C5 | 0.15461 (9) | 0.32023 (15) | 0.13792 (14) | 0.0628 (5) | |
H5A | 0.1801 | 0.3828 | 0.1673 | 0.075* | |
H5B | 0.1150 | 0.3470 | 0.0981 | 0.075* | |
C6 | 0.16966 (9) | 0.26095 (16) | 0.07125 (14) | 0.0637 (5) | |
C7 | 0.22652 (9) | 0.20004 (19) | 0.13549 (15) | 0.0705 (5) | |
H7A | 0.2350 | 0.1587 | 0.0940 | 0.085* | |
H7B | 0.2576 | 0.2524 | 0.1720 | 0.085* | |
C8 | 0.22509 (8) | 0.12410 (16) | 0.20596 (14) | 0.0624 (5) | |
C9 | 0.19083 (8) | 0.08003 (14) | 0.31875 (14) | 0.0598 (5) | |
H9 | 0.2299 | 0.0485 | 0.3587 | 0.072* | |
N10 | 0.13451 (7) | 0.28682 (11) | 0.26690 (11) | 0.0546 (4) | |
C11 | 0.16033 (7) | 0.24963 (14) | 0.21787 (12) | 0.0533 (4) | |
C12 | 0.19015 (8) | 0.15430 (14) | 0.24492 (12) | 0.0549 (4) | |
C13 | 0.18043 (8) | 0.14522 (14) | 0.38568 (13) | 0.0549 (4) | |
C14 | 0.15026 (7) | 0.23991 (14) | 0.35640 (13) | 0.0531 (4) | |
C15 | 0.08592 (10) | 0.14393 (19) | 0.45133 (18) | 0.0790 (6) | |
H15A | 0.0894 | 0.0980 | 0.4070 | 0.118* | |
H15B | 0.0492 | 0.1811 | 0.4162 | 0.118* | |
H15C | 0.0882 | 0.1002 | 0.5022 | 0.118* | |
C16 | 0.12988 (12) | 0.3003 (2) | 0.56749 (18) | 0.0864 (7) | |
H16A | 0.0929 | 0.3366 | 0.5327 | 0.130* | |
H16B | 0.1605 | 0.3536 | 0.5953 | 0.130* | |
H16C | 0.1329 | 0.2566 | 0.6190 | 0.130* | |
C17 | 0.12170 (10) | 0.18051 (19) | 0.00377 (15) | 0.0780 (6) | |
H17A | 0.1319 | 0.1444 | −0.0371 | 0.117* | |
H17B | 0.0858 | 0.2191 | −0.0366 | 0.117* | |
H17C | 0.1173 | 0.1275 | 0.0426 | 0.117* | |
C18 | 0.17534 (14) | 0.3461 (2) | 0.00786 (19) | 0.0927 (8) | |
H18A | 0.2052 | 0.3974 | 0.0495 | 0.139* | |
H18B | 0.1390 | 0.3837 | −0.0321 | 0.139* | |
H18C | 0.1853 | 0.3104 | −0.0335 | 0.139* | |
C19 | 0.10109 (8) | 0.38656 (14) | 0.23467 (13) | 0.0546 (4) | |
C20 | 0.04193 (9) | 0.38052 (17) | 0.16834 (19) | 0.0833 (7) | |
H20 | 0.0240 | 0.3132 | 0.1451 | 0.100* | |
C21 | 0.00942 (10) | 0.4745 (2) | 0.1365 (3) | 0.1083 (10) | |
H21 | −0.0306 | 0.4718 | 0.0917 | 0.130* | |
C22 | 0.03712 (11) | 0.57131 (18) | 0.1719 (2) | 0.0931 (8) | |
C23 | 0.09522 (10) | 0.57980 (15) | 0.23732 (17) | 0.0732 (6) | |
H23 | 0.1127 | 0.6476 | 0.2600 | 0.088* | |
C24 | 0.12802 (8) | 0.48571 (14) | 0.26964 (14) | 0.0600 (5) | |
H24 | 0.1680 | 0.4893 | 0.3147 | 0.072* | |
C25 | 0.14722 (11) | −0.01493 (16) | 0.27060 (18) | 0.0757 (6) | |
H25A | 0.1576 | −0.0578 | 0.2323 | 0.091* | |
H25B | 0.1512 | −0.0616 | 0.3221 | 0.091* | |
C26 | 0.08473 (11) | 0.01783 (19) | 0.2055 (2) | 0.0889 (7) | |
H26A | 0.0797 | 0.0587 | 0.1503 | 0.107* | |
H26B | 0.0749 | 0.0657 | 0.2418 | 0.107* | |
C27 | 0.04316 (16) | −0.0778 (3) | 0.1670 (3) | 0.1358 (13) | |
H27A | 0.0040 | −0.0516 | 0.1252 | 0.204* | |
H27B | 0.0468 | −0.1171 | 0.2210 | 0.204* | |
H27C | 0.0522 | −0.1251 | 0.1302 | 0.204* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.1171 (13) | 0.0653 (10) | 0.229 (2) | 0.0436 (9) | 0.0566 (14) | 0.0379 (12) |
O1 | 0.1021 (11) | 0.0873 (11) | 0.0796 (10) | 0.0452 (9) | 0.0524 (9) | 0.0350 (9) |
O2 | 0.0903 (10) | 0.0870 (11) | 0.0814 (10) | 0.0338 (9) | 0.0507 (8) | 0.0091 (8) |
C1 | 0.0611 (10) | 0.0588 (10) | 0.0640 (11) | 0.0100 (8) | 0.0326 (9) | 0.0141 (9) |
C2 | 0.0725 (11) | 0.0663 (12) | 0.0574 (10) | 0.0040 (9) | 0.0348 (9) | 0.0078 (9) |
C3 | 0.0753 (12) | 0.0569 (10) | 0.0652 (11) | 0.0039 (9) | 0.0443 (10) | 0.0044 (9) |
C4 | 0.0748 (11) | 0.0481 (9) | 0.0658 (11) | 0.0064 (8) | 0.0415 (10) | 0.0033 (8) |
C5 | 0.0821 (12) | 0.0466 (9) | 0.0607 (10) | −0.0030 (9) | 0.0397 (9) | 0.0020 (8) |
C6 | 0.0796 (12) | 0.0560 (10) | 0.0552 (10) | −0.0081 (9) | 0.0365 (9) | −0.0017 (8) |
C7 | 0.0732 (12) | 0.0778 (14) | 0.0679 (12) | −0.0054 (10) | 0.0432 (10) | −0.0060 (10) |
C8 | 0.0605 (10) | 0.0637 (11) | 0.0578 (10) | 0.0033 (9) | 0.0289 (8) | −0.0047 (9) |
C9 | 0.0671 (10) | 0.0493 (9) | 0.0652 (11) | 0.0146 (8) | 0.0375 (9) | 0.0095 (8) |
N10 | 0.0669 (8) | 0.0413 (7) | 0.0582 (8) | 0.0097 (6) | 0.0359 (7) | 0.0076 (6) |
C11 | 0.0582 (9) | 0.0447 (8) | 0.0535 (9) | −0.0025 (7) | 0.0282 (8) | −0.0024 (7) |
C12 | 0.0594 (9) | 0.0483 (9) | 0.0547 (9) | 0.0030 (7) | 0.0296 (8) | 0.0001 (7) |
C13 | 0.0592 (9) | 0.0471 (9) | 0.0585 (10) | 0.0074 (7) | 0.0322 (8) | 0.0067 (7) |
C14 | 0.0578 (9) | 0.0448 (8) | 0.0562 (9) | 0.0024 (7) | 0.0307 (8) | 0.0054 (7) |
C15 | 0.0758 (13) | 0.0759 (14) | 0.0966 (16) | 0.0005 (11) | 0.0543 (12) | 0.0088 (12) |
C16 | 0.1130 (18) | 0.0837 (16) | 0.0808 (15) | 0.0173 (14) | 0.0645 (14) | 0.0047 (12) |
C17 | 0.0829 (13) | 0.0711 (13) | 0.0606 (11) | −0.0057 (11) | 0.0269 (10) | −0.0089 (10) |
C18 | 0.133 (2) | 0.0789 (16) | 0.0850 (15) | −0.0073 (15) | 0.0719 (16) | 0.0074 (13) |
C19 | 0.0603 (9) | 0.0414 (9) | 0.0598 (9) | 0.0047 (7) | 0.0313 (8) | 0.0068 (7) |
C20 | 0.0619 (11) | 0.0513 (11) | 0.1052 (16) | −0.0032 (9) | 0.0253 (11) | 0.0030 (11) |
C21 | 0.0601 (12) | 0.0714 (15) | 0.143 (2) | 0.0112 (11) | 0.0227 (14) | 0.0191 (16) |
C22 | 0.0816 (15) | 0.0511 (12) | 0.125 (2) | 0.0230 (11) | 0.0423 (15) | 0.0244 (13) |
C23 | 0.0885 (14) | 0.0399 (9) | 0.0858 (14) | 0.0019 (9) | 0.0441 (12) | 0.0048 (9) |
C24 | 0.0631 (10) | 0.0472 (9) | 0.0636 (10) | 0.0010 (8) | 0.0307 (8) | 0.0022 (8) |
C25 | 0.1057 (16) | 0.0433 (10) | 0.0900 (15) | 0.0019 (10) | 0.0611 (14) | 0.0009 (10) |
C26 | 0.0950 (17) | 0.0615 (13) | 0.1085 (19) | −0.0149 (12) | 0.0544 (15) | −0.0122 (13) |
C27 | 0.130 (3) | 0.096 (2) | 0.196 (4) | −0.046 (2) | 0.099 (3) | −0.048 (2) |
Geometric parameters (Å, º) top
F1—C22 | 1.355 (2) | C13—C14 | 1.354 (2) |
O1—C1 | 1.227 (2) | C15—H15A | 0.9600 |
O2—C8 | 1.230 (2) | C15—H15B | 0.9600 |
C1—C13 | 1.456 (2) | C15—H15C | 0.9600 |
C1—C2 | 1.498 (3) | C16—H16A | 0.9600 |
C2—C3 | 1.518 (3) | C16—H16B | 0.9600 |
C2—H2A | 0.9700 | C16—H16C | 0.9600 |
C2—H2B | 0.9700 | C17—H17A | 0.9600 |
C3—C16 | 1.525 (3) | C17—H17B | 0.9600 |
C3—C15 | 1.530 (3) | C17—H17C | 0.9600 |
C3—C4 | 1.536 (2) | C18—H18A | 0.9600 |
C4—C14 | 1.503 (2) | C18—H18B | 0.9600 |
C4—H4A | 0.9700 | C18—H18C | 0.9600 |
C4—H4B | 0.9700 | C19—C24 | 1.375 (2) |
C5—C11 | 1.499 (2) | C19—C20 | 1.376 (3) |
C5—C6 | 1.539 (3) | C20—C21 | 1.375 (3) |
C5—H5A | 0.9700 | C20—H20 | 0.9300 |
C5—H5B | 0.9700 | C21—C22 | 1.358 (3) |
C6—C7 | 1.519 (3) | C21—H21 | 0.9300 |
C6—C17 | 1.528 (3) | C22—C23 | 1.354 (3) |
C6—C18 | 1.536 (3) | C23—C24 | 1.380 (3) |
C7—C8 | 1.496 (3) | C23—H23 | 0.9300 |
C7—H7A | 0.9700 | C24—H24 | 0.9300 |
C7—H7B | 0.9700 | C25—C26 | 1.497 (3) |
C8—C12 | 1.457 (3) | C25—H25A | 0.9700 |
C9—C13 | 1.499 (2) | C25—H25B | 0.9700 |
C9—C12 | 1.501 (2) | C26—C27 | 1.513 (3) |
C9—C25 | 1.543 (3) | C26—H26A | 0.9700 |
C9—H9 | 0.9800 | C26—H26B | 0.9700 |
N10—C14 | 1.398 (2) | C27—H27A | 0.9600 |
N10—C11 | 1.402 (2) | C27—H27B | 0.9600 |
N10—C19 | 1.446 (2) | C27—H27C | 0.9600 |
C11—C12 | 1.356 (2) | | |
| | | |
O1—C1—C13 | 120.36 (18) | N10—C14—C4 | 117.45 (14) |
O1—C1—C2 | 121.10 (17) | C3—C15—H15A | 109.5 |
C13—C1—C2 | 118.48 (16) | C3—C15—H15B | 109.5 |
C1—C2—C3 | 113.51 (16) | H15A—C15—H15B | 109.5 |
C1—C2—H2A | 108.9 | C3—C15—H15C | 109.5 |
C3—C2—H2A | 108.9 | H15A—C15—H15C | 109.5 |
C1—C2—H2B | 108.9 | H15B—C15—H15C | 109.5 |
C3—C2—H2B | 108.9 | C3—C16—H16A | 109.5 |
H2A—C2—H2B | 107.7 | C3—C16—H16B | 109.5 |
C2—C3—C16 | 109.85 (18) | H16A—C16—H16B | 109.5 |
C2—C3—C15 | 109.63 (17) | C3—C16—H16C | 109.5 |
C16—C3—C15 | 109.45 (17) | H16A—C16—H16C | 109.5 |
C2—C3—C4 | 107.98 (15) | H16B—C16—H16C | 109.5 |
C16—C3—C4 | 108.82 (16) | C6—C17—H17A | 109.5 |
C15—C3—C4 | 111.09 (17) | C6—C17—H17B | 109.5 |
C14—C4—C3 | 113.38 (15) | H17A—C17—H17B | 109.5 |
C14—C4—H4A | 108.9 | C6—C17—H17C | 109.5 |
C3—C4—H4A | 108.9 | H17A—C17—H17C | 109.5 |
C14—C4—H4B | 108.9 | H17B—C17—H17C | 109.5 |
C3—C4—H4B | 108.9 | C6—C18—H18A | 109.5 |
H4A—C4—H4B | 107.7 | C6—C18—H18B | 109.5 |
C11—C5—C6 | 113.45 (15) | H18A—C18—H18B | 109.5 |
C11—C5—H5A | 108.9 | C6—C18—H18C | 109.5 |
C6—C5—H5A | 108.9 | H18A—C18—H18C | 109.5 |
C11—C5—H5B | 108.9 | H18B—C18—H18C | 109.5 |
C6—C5—H5B | 108.9 | C24—C19—C20 | 120.62 (17) |
H5A—C5—H5B | 107.7 | C24—C19—N10 | 120.53 (16) |
C7—C6—C17 | 109.57 (17) | C20—C19—N10 | 118.84 (16) |
C7—C6—C18 | 110.77 (19) | C21—C20—C19 | 119.7 (2) |
C17—C6—C18 | 108.70 (18) | C21—C20—H20 | 120.1 |
C7—C6—C5 | 108.55 (15) | C19—C20—H20 | 120.1 |
C17—C6—C5 | 110.75 (17) | C22—C21—C20 | 118.4 (2) |
C18—C6—C5 | 108.49 (17) | C22—C21—H21 | 120.8 |
C8—C7—C6 | 112.80 (16) | C20—C21—H21 | 120.8 |
C8—C7—H7A | 109.0 | C23—C22—F1 | 118.8 (2) |
C6—C7—H7A | 109.0 | C23—C22—C21 | 123.2 (2) |
C8—C7—H7B | 109.0 | F1—C22—C21 | 118.1 (2) |
C6—C7—H7B | 109.0 | C22—C23—C24 | 118.61 (19) |
H7A—C7—H7B | 107.8 | C22—C23—H23 | 120.7 |
O2—C8—C12 | 120.33 (18) | C24—C23—H23 | 120.7 |
O2—C8—C7 | 121.29 (18) | C19—C24—C23 | 119.44 (18) |
C12—C8—C7 | 118.34 (17) | C19—C24—H24 | 120.3 |
C13—C9—C12 | 109.51 (14) | C23—C24—H24 | 120.3 |
C13—C9—C25 | 111.65 (16) | C26—C25—C9 | 115.32 (17) |
C12—C9—C25 | 112.68 (16) | C26—C25—H25A | 108.4 |
C13—C9—H9 | 107.6 | C9—C25—H25A | 108.4 |
C12—C9—H9 | 107.6 | C26—C25—H25B | 108.4 |
C25—C9—H9 | 107.6 | C9—C25—H25B | 108.4 |
C14—N10—C11 | 119.65 (14) | H25A—C25—H25B | 107.5 |
C14—N10—C19 | 120.07 (14) | C25—C26—C27 | 113.5 (2) |
C11—N10—C19 | 119.14 (14) | C25—C26—H26A | 108.9 |
C12—C11—N10 | 119.94 (16) | C27—C26—H26A | 108.9 |
C12—C11—C5 | 122.63 (17) | C25—C26—H26B | 108.9 |
N10—C11—C5 | 117.41 (15) | C27—C26—H26B | 108.9 |
C11—C12—C8 | 120.14 (16) | H26A—C26—H26B | 107.7 |
C11—C12—C9 | 121.70 (16) | C26—C27—H27A | 109.5 |
C8—C12—C9 | 118.09 (15) | C26—C27—H27B | 109.5 |
C14—C13—C1 | 119.95 (17) | H27A—C27—H27B | 109.5 |
C14—C13—C9 | 121.65 (16) | C26—C27—H27C | 109.5 |
C1—C13—C9 | 118.35 (15) | H27A—C27—H27C | 109.5 |
C13—C14—N10 | 120.16 (16) | H27B—C27—H27C | 109.5 |
C13—C14—C4 | 122.39 (16) | | |
| | | |
O1—C1—C2—C3 | −153.64 (19) | C2—C1—C13—C14 | 4.8 (3) |
C13—C1—C2—C3 | 29.0 (3) | O1—C1—C13—C9 | 5.0 (3) |
C1—C2—C3—C16 | −172.76 (17) | C2—C1—C13—C9 | −177.60 (17) |
C1—C2—C3—C15 | 66.9 (2) | C12—C9—C13—C14 | 26.8 (2) |
C1—C2—C3—C4 | −54.2 (2) | C25—C9—C13—C14 | −98.7 (2) |
C2—C3—C4—C14 | 48.9 (2) | C12—C9—C13—C1 | −150.80 (16) |
C16—C3—C4—C14 | 168.09 (17) | C25—C9—C13—C1 | 83.7 (2) |
C15—C3—C4—C14 | −71.4 (2) | C1—C13—C14—N10 | 169.03 (16) |
C11—C5—C6—C7 | −47.3 (2) | C9—C13—C14—N10 | −8.5 (3) |
C11—C5—C6—C17 | 73.1 (2) | C1—C13—C14—C4 | −10.2 (3) |
C11—C5—C6—C18 | −167.72 (18) | C9—C13—C14—C4 | 172.34 (17) |
C17—C6—C7—C8 | −65.9 (2) | C11—N10—C14—C13 | −13.8 (3) |
C18—C6—C7—C8 | 174.17 (17) | C19—N10—C14—C13 | 178.52 (16) |
C5—C6—C7—C8 | 55.2 (2) | C11—N10—C14—C4 | 165.39 (15) |
C6—C7—C8—O2 | 149.49 (19) | C19—N10—C14—C4 | −2.3 (2) |
C6—C7—C8—C12 | −32.7 (2) | C3—C4—C14—C13 | −18.3 (3) |
C14—N10—C11—C12 | 14.5 (3) | C3—C4—C14—N10 | 162.53 (16) |
C19—N10—C11—C12 | −177.74 (16) | C14—N10—C19—C24 | 81.4 (2) |
C14—N10—C11—C5 | −164.06 (16) | C11—N10—C19—C24 | −86.3 (2) |
C19—N10—C11—C5 | 3.7 (2) | C14—N10—C19—C20 | −98.7 (2) |
C6—C5—C11—C12 | 16.6 (3) | C11—N10—C19—C20 | 93.6 (2) |
C6—C5—C11—N10 | −164.88 (15) | C24—C19—C20—C21 | 0.2 (4) |
N10—C11—C12—C8 | −169.75 (16) | N10—C19—C20—C21 | −179.7 (2) |
C5—C11—C12—C8 | 8.7 (3) | C19—C20—C21—C22 | 0.1 (5) |
N10—C11—C12—C9 | 7.1 (3) | C20—C21—C22—C23 | −0.2 (5) |
C5—C11—C12—C9 | −174.39 (16) | C20—C21—C22—F1 | 179.9 (3) |
O2—C8—C12—C11 | 177.26 (18) | F1—C22—C23—C24 | 180.0 (2) |
C7—C8—C12—C11 | −0.6 (3) | C21—C22—C23—C24 | 0.1 (4) |
O2—C8—C12—C9 | 0.3 (3) | C20—C19—C24—C23 | −0.3 (3) |
C7—C8—C12—C9 | −177.53 (16) | N10—C19—C24—C23 | 179.62 (17) |
C13—C9—C12—C11 | −26.0 (2) | C22—C23—C24—C19 | 0.2 (3) |
C25—C9—C12—C11 | 98.9 (2) | C13—C9—C25—C26 | 62.7 (2) |
C13—C9—C12—C8 | 150.88 (16) | C12—C9—C25—C26 | −61.1 (2) |
C25—C9—C12—C8 | −84.2 (2) | C9—C25—C26—C27 | −175.0 (2) |
O1—C1—C13—C14 | −172.58 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O1 | 0.98 | 2.46 | 2.802 (2) | 100 |
C9—H9···O2 | 0.98 | 2.47 | 2.798 (4) | 99 |
C5—H5A···O2i | 0.97 | 2.53 | 3.494 (2) | 171 |
C24—H24···O1ii | 0.93 | 2.56 | 3.423 (3) | 155 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C24H28FNO2 | C26H32FNO2 |
Mr | 381.47 | 409.53 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, C2/c |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 17.1481 (2), 17.3909 (1), 15.8023 (3) | 27.454 (1), 12.2738 (10), 16.2792 (10) |
β (°) | 112.849 (1) | 123.118 (10) |
V (Å3) | 4342.79 (10) | 4594.4 (5) |
Z | 8 | 8 |
Radiation type | Mo Kα | Cu Kα |
µ (mm−1) | 0.08 | 0.63 |
Crystal size (mm) | 0.48 × 0.38 × 0.28 | 0.20 × 0.18 × 0.16 |
|
Data collection |
Diffractometer | Siemens SMART CCD area-detector diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | – |
Tmin, Tmax | 0.963, 0.978 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29750, 10547, 4439 | 4454, 4374, 3087 |
Rint | 0.075 | 0.053 |
(sin θ/λ)max (Å−1) | 0.667 | 0.619 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.188, 1.02 | 0.051, 0.196, 1.10 |
No. of reflections | 10547 | 4374 |
No. of parameters | 505 | 272 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.72, −0.27 | 0.17, −0.17 |
Selected geometric parameters (Å, º) for (I) topF1A—C22A | 1.359 (3) | F1B—C22B | 1.353 (2) |
O1A—C1A | 1.216 (3) | O1B—C1B | 1.227 (3) |
O2A—C8A | 1.232 (3) | O2B—C8B | 1.239 (2) |
N10A—C11A | 1.401 (3) | N10B—C11B | 1.399 (3) |
N10A—C14A | 1.401 (3) | N10B—C14B | 1.402 (2) |
N10A—C19A | 1.449 (3) | N10B—C19B | 1.453 (2) |
| | | |
C11A—N10A—C14A | 118.98 (18) | C11B—N10B—C14B | 120.13 (16) |
C11A—N10A—C19A | 120.14 (17) | C11B—N10B—C19B | 119.04 (17) |
C14A—N10A—C19A | 120.64 (17) | C14B—N10B—C19B | 119.81 (17) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9A—H9A···O1A | 0.98 | 2.51 | 2.850 (4) | 100 |
C9A—H9A···O2A | 0.98 | 2.52 | 2.856 (5) | 100 |
C9B—H9B···O1B | 0.98 | 2.51 | 2.828 (4) | 98 |
C9B—H9B···O2B | 0.98 | 2.53 | 2.819 (3) | 97 |
C24A—H24A···O2Ai | 0.93 | 2.50 | 3.247 (3) | 138 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Selected geometric parameters (Å, º) for (II) topF1—C22 | 1.355 (2) | N10—C14 | 1.398 (2) |
O1—C1 | 1.227 (2) | N10—C11 | 1.402 (2) |
O2—C8 | 1.230 (2) | N10—C19 | 1.446 (2) |
| | | |
C14—N10—C11 | 119.65 (14) | C11—N10—C19 | 119.14 (14) |
C14—N10—C19 | 120.07 (14) | | |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9···O1 | 0.98 | 2.46 | 2.802 (2) | 100 |
C9—H9···O2 | 0.98 | 2.47 | 2.798 (4) | 99 |
C5—H5A···O2i | 0.97 | 2.53 | 3.494 (2) | 171 |
C24—H24···O1ii | 0.93 | 2.56 | 3.423 (3) | 155 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z+1. |
Puckering (Å) and asymmetry parameters (Å) of the ring systems
in (I) and (II) topRing and molecule | Total puckering amplitude | Asymmetry parameters | Conformation |
A (Ia) | 0.395 (4) | ΔCs(C3A) = 0.072 (2) | Half-chair/sofa |
| | ΔC2(C3A-C2A) = 0.039 (1) | |
A (Ib) | 0.482 (3) | ΔCs(C3B) = 0.022 (1) | Half-chair/Sofa |
| | ΔC2(C3B-C2B) = 0.099 (1) | |
A (II) | 0.485 (2) | ΔCs(C3) = 0.039 (1) | Half-chair/Sofa |
| | ΔC2(C3-C2) = 0.089 (1) | |
B (Ia) | 0.370 (3) | ΔCs(N10A) = 0.005 (1) | Sofa |
B (Ib) | 0.255 (3) | ΔCs(N10B) = 0.007 (1) | Sofa |
B (II) | 0.281 (2) | ΔCs(N10) = 0.005 (1) | Sofa |
C (Ia) | 0.488 (2) | ΔCs(C6A) = 0.049 (1) | Half-chair/Sofa |
| | ΔC2(C7A-C6A) = 0.076 (1) | |
C (Ib) | 0.469 (3) | ΔCs(C6B) = 0.042 (2) | Half-chair/Sofa |
| | ΔC2(C7B-C6B) = 0.077 (1) | |
C (II) | 0.477 (2) | ΔCs(C6) = 0.062 (1) | Half-chair/Sofa |
| | ΔC2(C7-C6) = 0.067 (1) | |
Subscribe to Acta Crystallographica Section C: Structural Chemistry
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.
Acridine and its derivatives exhibit a wide spectrum of biological activities, such as antibacterial (Acheson et al., 1956), mutagenic and antitumour (Talacki et al., 1974), and antiamoebic (Prasad Krishna et al., 1984). The potency of acridines as antiviral and antibacterial agents is due to their ability to bind DNA by intercalation (Neidle, 1979; Nandi et al., 1990). Substitutions at C9 and N10 make the central ring of acridine buckled along the C9···N10 direction, with a dihedral angle formed by the two halves ranging from 7 to 13°. These values are smaller than those found in the present work. This buckling was postulated as the cause of their biological properties by Glusker et al. (1972). In acridine-1,8-diones, the electron delocalization is along a stretch of nine non-H atoms (O1 ═ C1—C13═C14—N10—C11═C12—C8═O2) which facilitate the exhibition of fluorescence and laser activity (Selladurai et al., 1990). The effectiveness of this laser activity can be controlled by the substituents at the 9- and 10-positions of the acridine chromophore. The decahydroacridine-1,8-diones act as photo-sensitizers (Timpe et al., 1993). Acridinediones have also been found to act as laser dyes, acting at around 475–495 nm (Murugan et al., 1998). The present study of the title compounds, (I) and (II), is a part of a series of investigations on the crystal structures of acridinedione derivatives. \sch
Compound (I) has two molecules in the asymmetric unit, designated (Ia) and (Ib). Fig. 1 shows the molecular structure and the atom-labelling scheme for both (Ia) and (Ib). Compound (II) has one molecule per asymmetric unit and Fig. 2 shows the molecular structure and atom-labelling scheme for (II).
The bond lengths C═O and Csp2—F in both structures are comparable with the values found in the literature (Allen et al., 1987). The average C═O [1.224 (3) Å in (Ia), 1.233 (3) Å in (Ib) and 1.228 (3) Å in (II)] and N—C [1.417 (3) Å in (Ia), 1.418 (2) Å in (Ib) and 1.415 (3) Å in (II)] bond lengths agree well with the values in several related structures (Jeyakanthan et al., 2000; Gunasekaran et al., 1996; Britto-Arias et al., 1996). Selected geometric parameters are given in Tables 1 and 3.
The acridine moiety is folded about the line passing through atoms C9 and N10, and the dihedral angle between the two halves is 27.4 (1)° in (Ia), 18.8 (1)° in (Ib) and 21.5 (1)° in (II). These values compare well with those reported in similar acridine derivatives (Gunasekaran et al., 1996; Sivaraman et al., 1994, 1996). The dihedral angle between the outer rings A and C of the acridine moiety is 18.0 (1)° in (Ia), 9.1 (1)° in (Ib) and 15.0 (1)° in (II) and this shows considerable buckling of the acridine nucleus.
The phenyl ring D in both structures is orthogonal to the central ring B, forming a dihedral angle of 88.3 (1)° in (Ia), 87.1 (1)° in (Ib) and 87.5 (1)° in (II). The valence angles around the N atom in both structures sum to 359.8 (2)° in (Ia), 359.0 (2)° in (Ib) and 358.9 (2)° in (II), and these values are indicative of sp2 hybridization of the nitrogen.
The C25A and C25B methyls in (I) and the C25 propyl in (II) are axial, as indicated by the angles formed by the C9—C25 and C9—H9 bonds with the plane through O1/C1/C13/C14/C11/C12/C8/O2 [C9A—C25A 88.1, C9A—H9A 21, C9B—C25B 77.6 and C9B—H9B 30° in (I), and C9—C25 79.7 and C9—H9 18° in (II)]. The deviation of atoms O1 and O2 from the mean planes passing through rings A and C are 0.144 (3) and 0.175 (2) Å in (Ia), 0.022 (2) and 0.098 (2) Å in (Ib) and 0.018 (2) and 0.101 (2) Å in (II), respectively.
The puckering amplitudes (Cremer & Pople, 1975) of the rings in the acridine moiety (Table 5) agree well with those of related structures (Gunasekaran et al., 1997; Jeyakanthan et al., 2000). The conformations of the rings of the acridine moiety in both structures are defined by the asymmetry parameters (Nardelli, 1983a), also given in Table 5.
In addition to the normal van der Waals interactions, the packing of the crystals in both structures is stabilized by C—H···O intermolecular hydrogen bonds. In (I), an intermolecular C—H···O hydrogen bond joins the molecules in a chain along the b direction. In (II), four C—H···O interactions occur with H···O distances less than the sum of the van der Waals radii (Bondi, 1964) (Table 4). In this structure, the acridine molecules are stacked in a head-to-head manner (Dauter et al., 1976) and are alternately parallel to each other. This type of stacking is also found in acridinedione (Sivaraman et al., 1996) and 9-amino acridine structures (Talacki et al., 1974).