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In the title compound, C31H27N, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431461602006X/sj4075sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431461602006X/sj4075Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S241431461602006X/sj4075Isup3.cml
Supplementary material

CCDC reference: 1523351

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](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

Computing details top

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-9H-fluoren-2-amine top
Crystal data top
C31H27NF(000) = 880
Mr = 413.54Dx = 1.139 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5915 reflections
a = 12.7365 (7) Åθ = 2.3–28.4°
b = 10.5803 (9) ŵ = 0.07 mm1
c = 18.6662 (11) ÅT = 296 K
β = 106.531 (3)°Block, yellow
V = 2411.4 (3) Å30.40 × 0.30 × 0.20 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5915 independent reflections
Radiation source: fine-focus sealed tube2979 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
ω and φ scanθmax = 28.4°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1616
Tmin = 0.974, Tmax = 0.987k = 1113
17899 measured reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-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 reflectionsΔρmax = 0.23 e Å3
290 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction 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
xyzUiso*/Ueq
C210.55085 (16)0.2135 (2)1.03753 (10)0.0643 (6)
H210.55080.15281.07350.077*
C220.64185 (16)0.2875 (3)1.04460 (12)0.0740 (7)
H220.70340.27561.08510.089*
C230.64316 (17)0.3774 (3)0.99344 (14)0.0766 (7)
H230.70510.42710.99880.092*
C240.55307 (17)0.3948 (2)0.93396 (12)0.0768 (7)
H240.55370.45680.89880.092*
C250.46098 (16)0.3210 (2)0.92554 (10)0.0644 (6)
H250.39980.33360.88480.077*
C200.45945 (14)0.2291 (2)0.97722 (9)0.0505 (5)
C270.36126 (15)0.0663 (2)0.84942 (10)0.0546 (5)
H270.43320.09190.85600.066*
C280.30536 (17)0.0053 (2)0.78493 (10)0.0608 (5)
H280.34000.00940.74810.073*
C290.19913 (17)0.0347 (2)0.77381 (11)0.0640 (6)
H290.16180.07520.72970.077*
C300.14928 (16)0.0136 (2)0.82890 (11)0.0642 (6)
H300.07810.04190.82250.077*
C310.20344 (14)0.0488 (2)0.89339 (10)0.0562 (5)
H310.16800.06370.92980.067*
C260.31065 (14)0.08984 (19)0.90484 (9)0.0474 (4)
C20.32513 (15)0.1446 (2)1.03489 (9)0.0538 (5)
C10.31211 (14)0.0285 (2)1.06600 (9)0.0514 (5)
H10.33270.04571.04700.062*
C100.26812 (14)0.02479 (19)1.12564 (9)0.0477 (5)
C110.23914 (14)0.1362 (2)1.15521 (9)0.0518 (5)
C40.25459 (17)0.2518 (2)1.12523 (11)0.0687 (6)
H40.23650.32641.14520.082*
C30.29750 (17)0.2546 (2)1.06483 (11)0.0682 (6)
H30.30780.33201.04420.082*
C90.24326 (14)0.0910 (2)1.16669 (9)0.0520 (5)
C160.16364 (17)0.1821 (2)1.11368 (11)0.0719 (6)
H16A0.20130.22111.08100.086*
H16B0.14410.24871.14320.086*
C170.06195 (19)0.1228 (3)1.06713 (14)0.0999 (9)
H17A0.01730.18571.03560.150*
H17B0.08000.05791.03670.150*
H17C0.02250.08631.09880.150*
C140.34677 (18)0.1643 (3)1.20693 (12)0.0773 (7)
H14A0.32550.23751.23080.093*
H14B0.38070.19491.16980.093*
C150.43024 (18)0.0919 (3)1.26448 (13)0.0985 (9)
H15A0.49170.14551.28660.148*
H15B0.39860.06301.30250.148*
H15C0.45410.02051.24150.148*
C130.19257 (14)0.0270 (2)1.22260 (9)0.0509 (5)
C80.15084 (14)0.0827 (2)1.27558 (10)0.0600 (5)
H80.15020.17021.28000.072*
C70.10976 (15)0.0069 (3)1.32245 (10)0.0622 (6)
C60.11196 (16)0.1229 (3)1.31574 (10)0.0693 (7)
H60.08590.17291.34790.083*
C50.15192 (16)0.1802 (2)1.26230 (10)0.0660 (6)
H50.15170.26771.25760.079*
C120.19252 (14)0.1035 (2)1.21568 (9)0.0518 (5)
C180.06541 (18)0.0628 (3)1.37757 (12)0.0861 (8)
C190.0276 (3)0.1050 (4)1.42180 (17)0.1355 (14)
H190.00280.13901.45730.163*
N10.36621 (12)0.15140 (17)0.97122 (7)0.0590 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C210.0670 (12)0.0672 (16)0.0527 (11)0.0011 (11)0.0077 (9)0.0075 (10)
C220.0524 (12)0.0841 (19)0.0727 (13)0.0025 (12)0.0028 (10)0.0065 (13)
C230.0582 (13)0.0771 (19)0.0940 (16)0.0180 (12)0.0205 (12)0.0110 (14)
C240.0750 (15)0.0739 (18)0.0801 (14)0.0177 (12)0.0196 (12)0.0172 (13)
C250.0574 (11)0.0753 (16)0.0556 (11)0.0088 (11)0.0083 (9)0.0125 (11)
C200.0503 (10)0.0575 (14)0.0459 (9)0.0052 (9)0.0173 (8)0.0029 (9)
C270.0548 (10)0.0615 (14)0.0500 (10)0.0019 (9)0.0188 (8)0.0014 (9)
C280.0759 (13)0.0580 (14)0.0529 (10)0.0068 (11)0.0257 (10)0.0049 (10)
C290.0744 (13)0.0572 (15)0.0549 (11)0.0053 (11)0.0094 (10)0.0105 (10)
C300.0560 (11)0.0712 (16)0.0619 (12)0.0090 (10)0.0108 (10)0.0009 (11)
C310.0530 (11)0.0673 (15)0.0501 (10)0.0038 (9)0.0174 (8)0.0016 (9)
C260.0512 (10)0.0503 (12)0.0418 (8)0.0019 (8)0.0150 (7)0.0035 (8)
C20.0601 (11)0.0611 (14)0.0441 (9)0.0130 (9)0.0211 (8)0.0031 (9)
C10.0587 (11)0.0550 (13)0.0443 (9)0.0039 (9)0.0206 (8)0.0038 (9)
C100.0529 (10)0.0531 (13)0.0386 (8)0.0046 (9)0.0154 (7)0.0011 (8)
C110.0606 (11)0.0532 (14)0.0462 (9)0.0104 (9)0.0226 (8)0.0066 (9)
C40.0982 (16)0.0506 (15)0.0712 (13)0.0120 (12)0.0465 (12)0.0089 (11)
C30.0951 (15)0.0522 (14)0.0692 (12)0.0147 (11)0.0427 (12)0.0003 (11)
C90.0597 (11)0.0541 (13)0.0463 (9)0.0010 (9)0.0214 (8)0.0038 (9)
C160.0879 (15)0.0630 (16)0.0703 (13)0.0146 (12)0.0315 (12)0.0076 (11)
C170.0784 (17)0.120 (3)0.0949 (17)0.0123 (16)0.0142 (14)0.0243 (17)
C140.0819 (15)0.0798 (19)0.0796 (14)0.0173 (13)0.0384 (12)0.0197 (13)
C150.0623 (14)0.149 (3)0.0800 (15)0.0118 (16)0.0137 (12)0.0062 (17)
C130.0496 (10)0.0641 (15)0.0393 (9)0.0024 (9)0.0132 (8)0.0036 (9)
C80.0587 (11)0.0731 (16)0.0501 (10)0.0004 (10)0.0182 (9)0.0124 (10)
C70.0539 (11)0.0919 (19)0.0427 (10)0.0035 (11)0.0168 (8)0.0059 (11)
C60.0666 (13)0.098 (2)0.0517 (11)0.0093 (12)0.0304 (10)0.0158 (12)
C50.0758 (13)0.0680 (16)0.0626 (12)0.0131 (11)0.0332 (10)0.0150 (11)
C120.0541 (10)0.0615 (15)0.0430 (9)0.0090 (9)0.0187 (8)0.0064 (9)
C180.0724 (14)0.135 (3)0.0576 (12)0.0028 (14)0.0290 (11)0.0205 (14)
C190.124 (2)0.203 (4)0.101 (2)0.006 (2)0.0660 (19)0.058 (2)
N10.0655 (10)0.0740 (13)0.0426 (8)0.0238 (9)0.0235 (7)0.0060 (8)
Geometric parameters (Å, º) top
C21—C221.373 (3)C11—C121.459 (2)
C21—C201.380 (2)C4—C31.386 (3)
C21—H210.9300C4—H40.9300
C22—C231.351 (3)C3—H30.9300
C22—H220.9300C9—C141.529 (3)
C23—C241.363 (3)C9—C131.532 (2)
C23—H230.9300C9—C161.538 (3)
C24—C251.380 (3)C16—C171.478 (3)
C24—H240.9300C16—H16A0.9700
C25—C201.374 (3)C16—H16B0.9700
C25—H250.9300C17—H17A0.9600
C20—N11.422 (2)C17—H17B0.9600
C27—C281.373 (3)C17—H17C0.9600
C27—C261.388 (2)C14—C151.490 (3)
C27—H270.9300C14—H14A0.9700
C28—C291.376 (3)C14—H14B0.9700
C28—H280.9300C15—H15A0.9600
C29—C301.372 (3)C15—H15B0.9600
C29—H290.9300C15—H15C0.9600
C30—C311.374 (3)C13—C81.381 (2)
C30—H300.9300C13—C121.387 (3)
C31—C261.390 (2)C8—C71.394 (3)
C31—H310.9300C8—H80.9300
C26—N11.400 (2)C7—C61.380 (3)
C2—C31.380 (3)C7—C181.434 (3)
C2—C11.389 (3)C6—C51.382 (3)
C2—N11.430 (2)C6—H60.9300
C1—C101.382 (2)C5—C121.392 (3)
C1—H10.9300C5—H50.9300
C10—C111.395 (3)C18—C191.158 (3)
C10—C91.525 (3)C19—H190.9300
C11—C41.383 (3)
C22—C21—C20120.2 (2)C10—C9—C14112.37 (15)
C22—C21—H21119.9C10—C9—C13100.07 (16)
C20—C21—H21119.9C14—C9—C13111.15 (14)
C23—C22—C21120.86 (19)C10—C9—C16111.90 (14)
C23—C22—H22119.6C14—C9—C16108.49 (19)
C21—C22—H22119.6C13—C9—C16112.75 (15)
C22—C23—C24119.6 (2)C17—C16—C9114.8 (2)
C22—C23—H23120.2C17—C16—H16A108.6
C24—C23—H23120.2C9—C16—H16A108.6
C23—C24—C25120.5 (2)C17—C16—H16B108.6
C23—C24—H24119.7C9—C16—H16B108.6
C25—C24—H24119.7H16A—C16—H16B107.5
C20—C25—C24120.11 (18)C16—C17—H17A109.5
C20—C25—H25119.9C16—C17—H17B109.5
C24—C25—H25119.9H17A—C17—H17B109.5
C25—C20—C21118.68 (18)C16—C17—H17C109.5
C25—C20—N1122.16 (16)H17A—C17—H17C109.5
C21—C20—N1119.15 (18)H17B—C17—H17C109.5
C28—C27—C26120.19 (17)C15—C14—C9115.6 (2)
C28—C27—H27119.9C15—C14—H14A108.4
C26—C27—H27119.9C9—C14—H14A108.4
C27—C28—C29121.27 (18)C15—C14—H14B108.4
C27—C28—H28119.4C9—C14—H14B108.4
C29—C28—H28119.4H14A—C14—H14B107.4
C30—C29—C28118.83 (18)C14—C15—H15A109.5
C30—C29—H29120.6C14—C15—H15B109.5
C28—C29—H29120.6H15A—C15—H15B109.5
C29—C30—C31120.71 (18)C14—C15—H15C109.5
C29—C30—H30119.6H15A—C15—H15C109.5
C31—C30—H30119.6H15B—C15—H15C109.5
C30—C31—C26120.73 (18)C8—C13—C12120.10 (18)
C30—C31—H31119.6C8—C13—C9128.4 (2)
C26—C31—H31119.6C12—C13—C9111.46 (15)
C27—C26—C31118.25 (16)C13—C8—C7119.6 (2)
C27—C26—N1121.20 (15)C13—C8—H8120.2
C31—C26—N1120.55 (15)C7—C8—H8120.2
C3—C2—C1120.17 (17)C6—C7—C8119.62 (19)
C3—C2—N1119.33 (19)C6—C7—C18119.8 (2)
C1—C2—N1120.50 (18)C8—C7—C18120.6 (2)
C10—C1—C2119.07 (19)C7—C6—C5121.5 (2)
C10—C1—H1120.5C7—C6—H6119.2
C2—C1—H1120.5C5—C6—H6119.2
C1—C10—C11120.56 (18)C6—C5—C12118.3 (2)
C1—C10—C9128.10 (18)C6—C5—H5120.9
C11—C10—C9111.33 (15)C12—C5—H5120.9
C4—C11—C10120.23 (17)C13—C12—C5120.81 (18)
C4—C11—C12131.22 (19)C13—C12—C11108.57 (16)
C10—C11—C12108.53 (17)C5—C12—C11130.6 (2)
C11—C4—C3118.9 (2)C19—C18—C7178.1 (3)
C11—C4—H4120.6C18—C19—H19180.0
C3—C4—H4120.6C26—N1—C20122.60 (14)
C2—C3—C4121.1 (2)C26—N1—C2119.97 (14)
C2—C3—H3119.5C20—N1—C2117.29 (14)
C4—C3—H3119.5
C20—C21—C22—C230.8 (4)C13—C9—C14—C1551.7 (2)
C21—C22—C23—C240.1 (4)C16—C9—C14—C15176.18 (18)
C22—C23—C24—C250.3 (4)C10—C9—C13—C8178.72 (17)
C23—C24—C25—C200.1 (4)C14—C9—C13—C862.4 (2)
C24—C25—C20—C210.8 (3)C16—C9—C13—C859.7 (2)
C24—C25—C20—N1179.5 (2)C10—C9—C13—C121.77 (17)
C22—C21—C20—C251.1 (3)C14—C9—C13—C12117.12 (19)
C22—C21—C20—N1179.93 (19)C16—C9—C13—C12120.81 (18)
C26—C27—C28—C290.5 (3)C12—C13—C8—C70.6 (2)
C27—C28—C29—C300.6 (3)C9—C13—C8—C7178.83 (16)
C28—C29—C30—C311.5 (3)C13—C8—C7—C60.5 (3)
C29—C30—C31—C261.2 (3)C13—C8—C7—C18179.61 (17)
C28—C27—C26—C310.8 (3)C8—C7—C6—C51.4 (3)
C28—C27—C26—N1179.70 (19)C18—C7—C6—C5178.63 (18)
C30—C31—C26—C270.1 (3)C7—C6—C5—C121.3 (3)
C30—C31—C26—N1178.85 (18)C8—C13—C12—C50.8 (3)
C3—C2—C1—C102.0 (3)C9—C13—C12—C5178.76 (15)
N1—C2—C1—C10177.44 (15)C8—C13—C12—C11179.06 (14)
C2—C1—C10—C111.2 (3)C9—C13—C12—C111.39 (19)
C2—C1—C10—C9177.93 (16)C6—C5—C12—C130.2 (3)
C1—C10—C11—C40.3 (3)C6—C5—C12—C11179.97 (17)
C9—C10—C11—C4179.56 (17)C4—C11—C12—C13178.18 (19)
C1—C10—C11—C12178.43 (15)C10—C11—C12—C130.3 (2)
C9—C10—C11—C120.87 (19)C4—C11—C12—C51.7 (3)
C10—C11—C4—C31.0 (3)C10—C11—C12—C5179.85 (18)
C12—C11—C4—C3177.32 (17)C6—C7—C18—C1932 (10)
C1—C2—C3—C41.2 (3)C8—C7—C18—C19148 (10)
N1—C2—C3—C4178.21 (16)C27—C26—N1—C2021.4 (3)
C11—C4—C3—C20.3 (3)C31—C26—N1—C20159.70 (19)
C1—C10—C9—C1464.3 (2)C27—C26—N1—C2163.01 (19)
C11—C10—C9—C14116.43 (18)C31—C26—N1—C215.9 (3)
C1—C10—C9—C13177.68 (16)C25—C20—N1—C2648.3 (3)
C11—C10—C9—C131.56 (17)C21—C20—N1—C26132.9 (2)
C1—C10—C9—C1658.0 (2)C25—C20—N1—C2127.4 (2)
C11—C10—C9—C16121.22 (17)C21—C20—N1—C251.4 (3)
C10—C9—C16—C1751.9 (2)C3—C2—N1—C26120.5 (2)
C14—C9—C16—C17176.40 (18)C1—C2—N1—C2658.9 (2)
C13—C9—C16—C1760.0 (2)C3—C2—N1—C2055.3 (2)
C10—C9—C14—C1559.6 (2)C1—C2—N1—C20125.3 (2)
Hydrogen-bond geometry (Å, º) top
Cg1 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···AD—HH···AD···AD—H···A
C5—H5···Cg1i0.932.763.508 (3)138
C30—H30···Cg2ii0.932.943.764 (2)149
Symmetry codes: (i) x, y1/2, z1/2; (ii) x, y, z.
 

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