In the title compound, C
31H
27N, the fluorene unit is approximately planar (r.m.s deviation = 0.0255 Å). The dihedral angles between the fluorene fused ring system and two phenyl rings are 88.37 (5) and 66.31 (6)°. Weak intermolecular C—H
π(ring) interactions help to stabilize the crystal structure.
Supporting information
CCDC reference: 1523351
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.055
- wR factor = 0.181
- Data-to-parameter ratio = 20.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 -- C14 .. 6.0 s.u.
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ... -2.289 Report
Alert level G
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
PLAT371_ALERT_2_G Long C(sp2)-C(sp1) Bond C7 - C18 .. 1.43 Ang.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 65 Do !
C6 -C7 -C18 -C19 32.00 10.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 66 Do !
C8 -C7 -C18 -C19 -148.00 10.00 1.555 1.555 1.555 1.555
PLAT899_ALERT_4_G SHELXL97 is Deprecated and Succeeded by SHELXL 2014 Note
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min) 2 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 89 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 4 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
9 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
4 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (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); software used to prepare material for publication: PLATON (Spek, 2009).
9,9-Diethyl-7-ethynyl-
N,
N-diphenyl-9
H-fluoren-2-amine
top
Crystal data top
C31H27N | F(000) = 880 |
Mr = 413.54 | Dx = 1.139 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5915 reflections |
a = 12.7365 (7) Å | θ = 2.3–28.4° |
b = 10.5803 (9) Å | µ = 0.07 mm−1 |
c = 18.6662 (11) Å | T = 296 K |
β = 106.531 (3)° | Block, yellow |
V = 2411.4 (3) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker Kappa APEXII CCD diffractometer | 5915 independent reflections |
Radiation source: fine-focus sealed tube | 2979 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω and φ scan | θmax = 28.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −16→16 |
Tmin = 0.974, Tmax = 0.987 | k = −11→13 |
17899 measured reflections | l = −24→24 |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.181 | w = 1/[σ2(Fo2) + (0.0937P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max = 0.001 |
5915 reflections | Δρmax = 0.23 e Å−3 |
290 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0103 (17) |
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 | |
C21 | 0.55085 (16) | 0.2135 (2) | 1.03753 (10) | 0.0643 (6) | |
H21 | 0.5508 | 0.1528 | 1.0735 | 0.077* | |
C22 | 0.64185 (16) | 0.2875 (3) | 1.04460 (12) | 0.0740 (7) | |
H22 | 0.7034 | 0.2756 | 1.0851 | 0.089* | |
C23 | 0.64316 (17) | 0.3774 (3) | 0.99344 (14) | 0.0766 (7) | |
H23 | 0.7051 | 0.4271 | 0.9988 | 0.092* | |
C24 | 0.55307 (17) | 0.3948 (2) | 0.93396 (12) | 0.0768 (7) | |
H24 | 0.5537 | 0.4568 | 0.8988 | 0.092* | |
C25 | 0.46098 (16) | 0.3210 (2) | 0.92554 (10) | 0.0644 (6) | |
H25 | 0.3998 | 0.3336 | 0.8848 | 0.077* | |
C20 | 0.45945 (14) | 0.2291 (2) | 0.97722 (9) | 0.0505 (5) | |
C27 | 0.36126 (15) | 0.0663 (2) | 0.84942 (10) | 0.0546 (5) | |
H27 | 0.4332 | 0.0919 | 0.8560 | 0.066* | |
C28 | 0.30536 (17) | 0.0053 (2) | 0.78493 (10) | 0.0608 (5) | |
H28 | 0.3400 | −0.0094 | 0.7481 | 0.073* | |
C29 | 0.19913 (17) | −0.0347 (2) | 0.77381 (11) | 0.0640 (6) | |
H29 | 0.1618 | −0.0752 | 0.7297 | 0.077* | |
C30 | 0.14928 (16) | −0.0136 (2) | 0.82890 (11) | 0.0642 (6) | |
H30 | 0.0781 | −0.0419 | 0.8225 | 0.077* | |
C31 | 0.20344 (14) | 0.0488 (2) | 0.89339 (10) | 0.0562 (5) | |
H31 | 0.1680 | 0.0637 | 0.9298 | 0.067* | |
C26 | 0.31065 (14) | 0.08984 (19) | 0.90484 (9) | 0.0474 (4) | |
C2 | 0.32513 (15) | 0.1446 (2) | 1.03489 (9) | 0.0538 (5) | |
C1 | 0.31211 (14) | 0.0285 (2) | 1.06600 (9) | 0.0514 (5) | |
H1 | 0.3327 | −0.0457 | 1.0470 | 0.062* | |
C10 | 0.26812 (14) | 0.02479 (19) | 1.12564 (9) | 0.0477 (5) | |
C11 | 0.23914 (14) | 0.1362 (2) | 1.15521 (9) | 0.0518 (5) | |
C4 | 0.25459 (17) | 0.2518 (2) | 1.12523 (11) | 0.0687 (6) | |
H4 | 0.2365 | 0.3264 | 1.1452 | 0.082* | |
C3 | 0.29750 (17) | 0.2546 (2) | 1.06483 (11) | 0.0682 (6) | |
H3 | 0.3078 | 0.3320 | 1.0442 | 0.082* | |
C9 | 0.24326 (14) | −0.0910 (2) | 1.16669 (9) | 0.0520 (5) | |
C16 | 0.16364 (17) | −0.1821 (2) | 1.11368 (11) | 0.0719 (6) | |
H16A | 0.2013 | −0.2211 | 1.0810 | 0.086* | |
H16B | 0.1441 | −0.2487 | 1.1432 | 0.086* | |
C17 | 0.06195 (19) | −0.1228 (3) | 1.06713 (14) | 0.0999 (9) | |
H17A | 0.0173 | −0.1857 | 1.0356 | 0.150* | |
H17B | 0.0800 | −0.0579 | 1.0367 | 0.150* | |
H17C | 0.0225 | −0.0863 | 1.0988 | 0.150* | |
C14 | 0.34677 (18) | −0.1643 (3) | 1.20693 (12) | 0.0773 (7) | |
H14A | 0.3255 | −0.2375 | 1.2308 | 0.093* | |
H14B | 0.3807 | −0.1949 | 1.1698 | 0.093* | |
C15 | 0.43024 (18) | −0.0919 (3) | 1.26448 (13) | 0.0985 (9) | |
H15A | 0.4917 | −0.1455 | 1.2866 | 0.148* | |
H15B | 0.3986 | −0.0630 | 1.3025 | 0.148* | |
H15C | 0.4541 | −0.0205 | 1.2415 | 0.148* | |
C13 | 0.19257 (14) | −0.0270 (2) | 1.22260 (9) | 0.0509 (5) | |
C8 | 0.15084 (14) | −0.0827 (2) | 1.27558 (10) | 0.0600 (5) | |
H8 | 0.1502 | −0.1702 | 1.2800 | 0.072* | |
C7 | 0.10976 (15) | −0.0069 (3) | 1.32245 (10) | 0.0622 (6) | |
C6 | 0.11196 (16) | 0.1229 (3) | 1.31574 (10) | 0.0693 (7) | |
H6 | 0.0859 | 0.1729 | 1.3479 | 0.083* | |
C5 | 0.15192 (16) | 0.1802 (2) | 1.26230 (10) | 0.0660 (6) | |
H5 | 0.1517 | 0.2677 | 1.2576 | 0.079* | |
C12 | 0.19252 (14) | 0.1035 (2) | 1.21568 (9) | 0.0518 (5) | |
C18 | 0.06541 (18) | −0.0628 (3) | 1.37757 (12) | 0.0861 (8) | |
C19 | 0.0276 (3) | −0.1050 (4) | 1.42180 (17) | 0.1355 (14) | |
H19 | −0.0028 | −0.1390 | 1.4573 | 0.163* | |
N1 | 0.36621 (12) | 0.15140 (17) | 0.97122 (7) | 0.0590 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C21 | 0.0670 (12) | 0.0672 (16) | 0.0527 (11) | 0.0011 (11) | 0.0077 (9) | 0.0075 (10) |
C22 | 0.0524 (12) | 0.0841 (19) | 0.0727 (13) | 0.0025 (12) | −0.0028 (10) | −0.0065 (13) |
C23 | 0.0582 (13) | 0.0771 (19) | 0.0940 (16) | −0.0180 (12) | 0.0205 (12) | −0.0110 (14) |
C24 | 0.0750 (15) | 0.0739 (18) | 0.0801 (14) | −0.0177 (12) | 0.0196 (12) | 0.0172 (13) |
C25 | 0.0574 (11) | 0.0753 (16) | 0.0556 (11) | −0.0088 (11) | 0.0083 (9) | 0.0125 (11) |
C20 | 0.0503 (10) | 0.0575 (14) | 0.0459 (9) | −0.0052 (9) | 0.0173 (8) | −0.0029 (9) |
C27 | 0.0548 (10) | 0.0615 (14) | 0.0500 (10) | −0.0019 (9) | 0.0188 (8) | 0.0014 (9) |
C28 | 0.0759 (13) | 0.0580 (14) | 0.0529 (10) | 0.0068 (11) | 0.0257 (10) | −0.0049 (10) |
C29 | 0.0744 (13) | 0.0572 (15) | 0.0549 (11) | −0.0053 (11) | 0.0094 (10) | −0.0105 (10) |
C30 | 0.0560 (11) | 0.0712 (16) | 0.0619 (12) | −0.0090 (10) | 0.0108 (10) | 0.0009 (11) |
C31 | 0.0530 (11) | 0.0673 (15) | 0.0501 (10) | −0.0038 (9) | 0.0174 (8) | 0.0016 (9) |
C26 | 0.0512 (10) | 0.0503 (12) | 0.0418 (8) | −0.0019 (8) | 0.0150 (7) | 0.0035 (8) |
C2 | 0.0601 (11) | 0.0611 (14) | 0.0441 (9) | −0.0130 (9) | 0.0211 (8) | −0.0031 (9) |
C1 | 0.0587 (11) | 0.0550 (13) | 0.0443 (9) | −0.0039 (9) | 0.0206 (8) | −0.0038 (9) |
C10 | 0.0529 (10) | 0.0531 (13) | 0.0386 (8) | −0.0046 (9) | 0.0154 (7) | −0.0011 (8) |
C11 | 0.0606 (11) | 0.0532 (14) | 0.0462 (9) | −0.0104 (9) | 0.0226 (8) | −0.0066 (9) |
C4 | 0.0982 (16) | 0.0506 (15) | 0.0712 (13) | −0.0120 (12) | 0.0465 (12) | −0.0089 (11) |
C3 | 0.0951 (15) | 0.0522 (14) | 0.0692 (12) | −0.0147 (11) | 0.0427 (12) | 0.0003 (11) |
C9 | 0.0597 (11) | 0.0541 (13) | 0.0463 (9) | 0.0010 (9) | 0.0214 (8) | 0.0038 (9) |
C16 | 0.0879 (15) | 0.0630 (16) | 0.0703 (13) | −0.0146 (12) | 0.0315 (12) | −0.0076 (11) |
C17 | 0.0784 (17) | 0.120 (3) | 0.0949 (17) | −0.0123 (16) | 0.0142 (14) | −0.0243 (17) |
C14 | 0.0819 (15) | 0.0798 (19) | 0.0796 (14) | 0.0173 (13) | 0.0384 (12) | 0.0197 (13) |
C15 | 0.0623 (14) | 0.149 (3) | 0.0800 (15) | 0.0118 (16) | 0.0137 (12) | 0.0062 (17) |
C13 | 0.0496 (10) | 0.0641 (15) | 0.0393 (9) | −0.0024 (9) | 0.0132 (8) | 0.0036 (9) |
C8 | 0.0587 (11) | 0.0731 (16) | 0.0501 (10) | 0.0004 (10) | 0.0182 (9) | 0.0124 (10) |
C7 | 0.0539 (11) | 0.0919 (19) | 0.0427 (10) | −0.0035 (11) | 0.0168 (8) | 0.0059 (11) |
C6 | 0.0666 (13) | 0.098 (2) | 0.0517 (11) | −0.0093 (12) | 0.0304 (10) | −0.0158 (12) |
C5 | 0.0758 (13) | 0.0680 (16) | 0.0626 (12) | −0.0131 (11) | 0.0332 (10) | −0.0150 (11) |
C12 | 0.0541 (10) | 0.0615 (15) | 0.0430 (9) | −0.0090 (9) | 0.0187 (8) | −0.0064 (9) |
C18 | 0.0724 (14) | 0.135 (3) | 0.0576 (12) | 0.0028 (14) | 0.0290 (11) | 0.0205 (14) |
C19 | 0.124 (2) | 0.203 (4) | 0.101 (2) | 0.006 (2) | 0.0660 (19) | 0.058 (2) |
N1 | 0.0655 (10) | 0.0740 (13) | 0.0426 (8) | −0.0238 (9) | 0.0235 (7) | −0.0060 (8) |
Geometric parameters (Å, º) top
C21—C22 | 1.373 (3) | C11—C12 | 1.459 (2) |
C21—C20 | 1.380 (2) | C4—C3 | 1.386 (3) |
C21—H21 | 0.9300 | C4—H4 | 0.9300 |
C22—C23 | 1.351 (3) | C3—H3 | 0.9300 |
C22—H22 | 0.9300 | C9—C14 | 1.529 (3) |
C23—C24 | 1.363 (3) | C9—C13 | 1.532 (2) |
C23—H23 | 0.9300 | C9—C16 | 1.538 (3) |
C24—C25 | 1.380 (3) | C16—C17 | 1.478 (3) |
C24—H24 | 0.9300 | C16—H16A | 0.9700 |
C25—C20 | 1.374 (3) | C16—H16B | 0.9700 |
C25—H25 | 0.9300 | C17—H17A | 0.9600 |
C20—N1 | 1.422 (2) | C17—H17B | 0.9600 |
C27—C28 | 1.373 (3) | C17—H17C | 0.9600 |
C27—C26 | 1.388 (2) | C14—C15 | 1.490 (3) |
C27—H27 | 0.9300 | C14—H14A | 0.9700 |
C28—C29 | 1.376 (3) | C14—H14B | 0.9700 |
C28—H28 | 0.9300 | C15—H15A | 0.9600 |
C29—C30 | 1.372 (3) | C15—H15B | 0.9600 |
C29—H29 | 0.9300 | C15—H15C | 0.9600 |
C30—C31 | 1.374 (3) | C13—C8 | 1.381 (2) |
C30—H30 | 0.9300 | C13—C12 | 1.387 (3) |
C31—C26 | 1.390 (2) | C8—C7 | 1.394 (3) |
C31—H31 | 0.9300 | C8—H8 | 0.9300 |
C26—N1 | 1.400 (2) | C7—C6 | 1.380 (3) |
C2—C3 | 1.380 (3) | C7—C18 | 1.434 (3) |
C2—C1 | 1.389 (3) | C6—C5 | 1.382 (3) |
C2—N1 | 1.430 (2) | C6—H6 | 0.9300 |
C1—C10 | 1.382 (2) | C5—C12 | 1.392 (3) |
C1—H1 | 0.9300 | C5—H5 | 0.9300 |
C10—C11 | 1.395 (3) | C18—C19 | 1.158 (3) |
C10—C9 | 1.525 (3) | C19—H19 | 0.9300 |
C11—C4 | 1.383 (3) | | |
| | | |
C22—C21—C20 | 120.2 (2) | C10—C9—C14 | 112.37 (15) |
C22—C21—H21 | 119.9 | C10—C9—C13 | 100.07 (16) |
C20—C21—H21 | 119.9 | C14—C9—C13 | 111.15 (14) |
C23—C22—C21 | 120.86 (19) | C10—C9—C16 | 111.90 (14) |
C23—C22—H22 | 119.6 | C14—C9—C16 | 108.49 (19) |
C21—C22—H22 | 119.6 | C13—C9—C16 | 112.75 (15) |
C22—C23—C24 | 119.6 (2) | C17—C16—C9 | 114.8 (2) |
C22—C23—H23 | 120.2 | C17—C16—H16A | 108.6 |
C24—C23—H23 | 120.2 | C9—C16—H16A | 108.6 |
C23—C24—C25 | 120.5 (2) | C17—C16—H16B | 108.6 |
C23—C24—H24 | 119.7 | C9—C16—H16B | 108.6 |
C25—C24—H24 | 119.7 | H16A—C16—H16B | 107.5 |
C20—C25—C24 | 120.11 (18) | C16—C17—H17A | 109.5 |
C20—C25—H25 | 119.9 | C16—C17—H17B | 109.5 |
C24—C25—H25 | 119.9 | H17A—C17—H17B | 109.5 |
C25—C20—C21 | 118.68 (18) | C16—C17—H17C | 109.5 |
C25—C20—N1 | 122.16 (16) | H17A—C17—H17C | 109.5 |
C21—C20—N1 | 119.15 (18) | H17B—C17—H17C | 109.5 |
C28—C27—C26 | 120.19 (17) | C15—C14—C9 | 115.6 (2) |
C28—C27—H27 | 119.9 | C15—C14—H14A | 108.4 |
C26—C27—H27 | 119.9 | C9—C14—H14A | 108.4 |
C27—C28—C29 | 121.27 (18) | C15—C14—H14B | 108.4 |
C27—C28—H28 | 119.4 | C9—C14—H14B | 108.4 |
C29—C28—H28 | 119.4 | H14A—C14—H14B | 107.4 |
C30—C29—C28 | 118.83 (18) | C14—C15—H15A | 109.5 |
C30—C29—H29 | 120.6 | C14—C15—H15B | 109.5 |
C28—C29—H29 | 120.6 | H15A—C15—H15B | 109.5 |
C29—C30—C31 | 120.71 (18) | C14—C15—H15C | 109.5 |
C29—C30—H30 | 119.6 | H15A—C15—H15C | 109.5 |
C31—C30—H30 | 119.6 | H15B—C15—H15C | 109.5 |
C30—C31—C26 | 120.73 (18) | C8—C13—C12 | 120.10 (18) |
C30—C31—H31 | 119.6 | C8—C13—C9 | 128.4 (2) |
C26—C31—H31 | 119.6 | C12—C13—C9 | 111.46 (15) |
C27—C26—C31 | 118.25 (16) | C13—C8—C7 | 119.6 (2) |
C27—C26—N1 | 121.20 (15) | C13—C8—H8 | 120.2 |
C31—C26—N1 | 120.55 (15) | C7—C8—H8 | 120.2 |
C3—C2—C1 | 120.17 (17) | C6—C7—C8 | 119.62 (19) |
C3—C2—N1 | 119.33 (19) | C6—C7—C18 | 119.8 (2) |
C1—C2—N1 | 120.50 (18) | C8—C7—C18 | 120.6 (2) |
C10—C1—C2 | 119.07 (19) | C7—C6—C5 | 121.5 (2) |
C10—C1—H1 | 120.5 | C7—C6—H6 | 119.2 |
C2—C1—H1 | 120.5 | C5—C6—H6 | 119.2 |
C1—C10—C11 | 120.56 (18) | C6—C5—C12 | 118.3 (2) |
C1—C10—C9 | 128.10 (18) | C6—C5—H5 | 120.9 |
C11—C10—C9 | 111.33 (15) | C12—C5—H5 | 120.9 |
C4—C11—C10 | 120.23 (17) | C13—C12—C5 | 120.81 (18) |
C4—C11—C12 | 131.22 (19) | C13—C12—C11 | 108.57 (16) |
C10—C11—C12 | 108.53 (17) | C5—C12—C11 | 130.6 (2) |
C11—C4—C3 | 118.9 (2) | C19—C18—C7 | 178.1 (3) |
C11—C4—H4 | 120.6 | C18—C19—H19 | 180.0 |
C3—C4—H4 | 120.6 | C26—N1—C20 | 122.60 (14) |
C2—C3—C4 | 121.1 (2) | C26—N1—C2 | 119.97 (14) |
C2—C3—H3 | 119.5 | C20—N1—C2 | 117.29 (14) |
C4—C3—H3 | 119.5 | | |
| | | |
C20—C21—C22—C23 | 0.8 (4) | C13—C9—C14—C15 | −51.7 (2) |
C21—C22—C23—C24 | −0.1 (4) | C16—C9—C14—C15 | −176.18 (18) |
C22—C23—C24—C25 | −0.3 (4) | C10—C9—C13—C8 | 178.72 (17) |
C23—C24—C25—C20 | −0.1 (4) | C14—C9—C13—C8 | −62.4 (2) |
C24—C25—C20—C21 | 0.8 (3) | C16—C9—C13—C8 | 59.7 (2) |
C24—C25—C20—N1 | 179.5 (2) | C10—C9—C13—C12 | −1.77 (17) |
C22—C21—C20—C25 | −1.1 (3) | C14—C9—C13—C12 | 117.12 (19) |
C22—C21—C20—N1 | −179.93 (19) | C16—C9—C13—C12 | −120.81 (18) |
C26—C27—C28—C29 | −0.5 (3) | C12—C13—C8—C7 | −0.6 (2) |
C27—C28—C29—C30 | −0.6 (3) | C9—C13—C8—C7 | 178.83 (16) |
C28—C29—C30—C31 | 1.5 (3) | C13—C8—C7—C6 | −0.5 (3) |
C29—C30—C31—C26 | −1.2 (3) | C13—C8—C7—C18 | 179.61 (17) |
C28—C27—C26—C31 | 0.8 (3) | C8—C7—C6—C5 | 1.4 (3) |
C28—C27—C26—N1 | 179.70 (19) | C18—C7—C6—C5 | −178.63 (18) |
C30—C31—C26—C27 | 0.1 (3) | C7—C6—C5—C12 | −1.3 (3) |
C30—C31—C26—N1 | −178.85 (18) | C8—C13—C12—C5 | 0.8 (3) |
C3—C2—C1—C10 | 2.0 (3) | C9—C13—C12—C5 | −178.76 (15) |
N1—C2—C1—C10 | −177.44 (15) | C8—C13—C12—C11 | −179.06 (14) |
C2—C1—C10—C11 | −1.2 (3) | C9—C13—C12—C11 | 1.39 (19) |
C2—C1—C10—C9 | 177.93 (16) | C6—C5—C12—C13 | 0.2 (3) |
C1—C10—C11—C4 | −0.3 (3) | C6—C5—C12—C11 | 179.97 (17) |
C9—C10—C11—C4 | −179.56 (17) | C4—C11—C12—C13 | 178.18 (19) |
C1—C10—C11—C12 | 178.43 (15) | C10—C11—C12—C13 | −0.3 (2) |
C9—C10—C11—C12 | −0.87 (19) | C4—C11—C12—C5 | −1.7 (3) |
C10—C11—C4—C3 | 1.0 (3) | C10—C11—C12—C5 | 179.85 (18) |
C12—C11—C4—C3 | −177.32 (17) | C6—C7—C18—C19 | 32 (10) |
C1—C2—C3—C4 | −1.2 (3) | C8—C7—C18—C19 | −148 (10) |
N1—C2—C3—C4 | 178.21 (16) | C27—C26—N1—C20 | 21.4 (3) |
C11—C4—C3—C2 | −0.3 (3) | C31—C26—N1—C20 | −159.70 (19) |
C1—C10—C9—C14 | 64.3 (2) | C27—C26—N1—C2 | −163.01 (19) |
C11—C10—C9—C14 | −116.43 (18) | C31—C26—N1—C2 | 15.9 (3) |
C1—C10—C9—C13 | −177.68 (16) | C25—C20—N1—C26 | 48.3 (3) |
C11—C10—C9—C13 | 1.56 (17) | C21—C20—N1—C26 | −132.9 (2) |
C1—C10—C9—C16 | −58.0 (2) | C25—C20—N1—C2 | −127.4 (2) |
C11—C10—C9—C16 | 121.22 (17) | C21—C20—N1—C2 | 51.4 (3) |
C10—C9—C16—C17 | −51.9 (2) | C3—C2—N1—C26 | −120.5 (2) |
C14—C9—C16—C17 | −176.40 (18) | C1—C2—N1—C26 | 58.9 (2) |
C13—C9—C16—C17 | 60.0 (2) | C3—C2—N1—C20 | 55.3 (2) |
C10—C9—C14—C15 | 59.6 (2) | C1—C2—N1—C20 | −125.3 (2) |
Hydrogen-bond geometry (Å, º) topCg1 is the centroid of the C26–C31 phenyl ring and
Cg2 is the centroid of the C5–C8/C13/C12 phenyl ring of the fluorene
moiety. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg1i | 0.93 | 2.76 | 3.508 (3) | 138 |
C30—H30···Cg2ii | 0.93 | 2.94 | 3.764 (2) | 149 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) −x, −y, −z. |