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When grown from the melt, the title compound, C29H40Br2, crystallizes in a tetra­gonal space group. The octyl chains lie in planes parallel to the (100) and (010) planes of the unit cell. These chains extend in a direction almost perpendicular to the fluorene ring system, forcing a 13.5 Å separation between potentially overlapping parallel fluorenes, thereby preventing mol­ecular π–π stacking.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002881/bv6048sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002881/bv6048Isup2.hkl
Contains datablock I

CCDC reference: 298382

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.045
  • wR factor = 0.123
  • Data-to-parameter ratio = 20.7

checkCIF/PLATON results

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Alert level B PLAT094_ALERT_2_B Ratio of Maximum / Minimum Residual Density .... 4.30 PLAT230_ALERT_2_B Hirshfeld Test Diff for C11 - C12 .. 8.29 su PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 148.00 A   3
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.544 From the CIF: _refine_ls_abs_structure_Flack_su 0.013 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.54 PLAT230_ALERT_2_C Hirshfeld Test Diff for Br1 - C3 .. 6.65 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C9 - C10 .. 5.70 su
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.40 From the CIF: _reflns_number_total 5817 Count of symmetry unique reflns 3025 Completeness (_total/calc) 192.30% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2792 Fraction of Friedel pairs measured 0.923 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2003); software used to prepare material for publication: SHELXTL.

2,7-dibromo-9,9-di-n-octyl-9H-fluorene top
Crystal data top
C29H40Br2Dx = 1.282 Mg m3
Mr = 548.43Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4Cell parameters from 5835 reflections
Hall symbol: I -4θ = 2.2–26.2°
a = 18.7019 (5) ŵ = 2.87 mm1
c = 16.2506 (8) ÅT = 193 K
V = 5683.8 (4) Å3Prism, colourless
Z = 80.49 × 0.43 × 0.36 mm
F(000) = 2272
Data collection top
Bruker SMART 1000 CCD area-detector/PLATFORM
diffractometer
5817 independent reflections
Radiation source: fine-focus sealed tube4767 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 8.192 pixels mm-1θmax = 26.4°, θmin = 1.5°
ω scansh = 2323
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
k = 2323
Tmin = 0.280, Tmax = 0.356l = 2020
22528 measured reflections
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0792P)2 + 1.0462P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5817 reflectionsΔρmax = 1.26 e Å3
281 parametersΔρmin = 0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), with how many Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.544 (13)
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
xyzUiso*/Ueq
Br10.32720 (3)0.13941 (3)0.44836 (3)0.05784 (14)
Br20.32510 (3)0.14162 (3)0.20054 (3)0.07294 (17)
C10.3261 (2)0.16395 (17)0.1949 (2)0.0366 (8)
C20.3182 (2)0.1777 (2)0.2792 (3)0.0421 (9)
H20.30120.22240.29900.051*
C30.33604 (19)0.1235 (2)0.3311 (2)0.0348 (8)
C40.36300 (18)0.05793 (19)0.3074 (3)0.0414 (8)
H40.37560.02280.34710.050*
C50.37108 (19)0.04497 (19)0.2245 (3)0.0410 (9)
H50.38900.00030.20590.049*
C60.35271 (18)0.09808 (18)0.1679 (2)0.0358 (8)
C70.35356 (18)0.09887 (19)0.0785 (3)0.0391 (8)
C80.3726 (2)0.0464 (2)0.0218 (3)0.0488 (9)
H80.39100.00170.04000.059*
C90.3646 (2)0.0599 (3)0.0613 (3)0.0574 (11)
H90.37760.02500.10100.069*
C100.3373 (2)0.1256 (2)0.0857 (3)0.0503 (10)
C110.3188 (2)0.1750 (3)0.0312 (2)0.0433 (10)
H110.29950.21900.05030.052*
C120.3264 (2)0.16487 (18)0.0501 (2)0.0385 (8)
C130.30713 (16)0.21216 (15)0.1239 (3)0.0355 (6)
C140.22673 (16)0.23087 (16)0.1234 (3)0.0404 (7)
H14A0.21650.26120.17190.048*
H14B0.21660.25980.07380.048*
C150.17568 (17)0.16790 (17)0.1245 (3)0.0435 (7)
H15A0.18390.13960.17510.052*
H15B0.18590.13670.07670.052*
C160.09759 (17)0.19100 (18)0.1214 (3)0.0443 (7)
H16A0.08760.22310.16840.053*
H16B0.08910.21830.07010.053*
C170.04671 (18)0.12791 (19)0.1244 (4)0.0474 (8)
H17A0.05590.10060.17550.057*
H17B0.05720.09600.07730.057*
C180.03231 (18)0.14805 (19)0.1218 (4)0.0464 (8)
H18A0.04330.17980.16890.056*
H18B0.04210.17500.07060.056*
C190.08093 (18)0.08304 (19)0.1252 (4)0.0455 (8)
H19A0.06940.05490.17510.055*
H19B0.07120.05240.07670.055*
C200.16009 (18)0.1019 (2)0.1264 (4)0.0525 (9)
H20A0.17020.13130.17580.063*
H20B0.17140.13120.07740.063*
C210.2080 (2)0.0372 (2)0.1273 (4)0.0586 (9)
H21A0.25800.05250.13120.070*
H21B0.19600.00710.17470.070*
H21C0.20100.00990.07650.070*
C220.34911 (16)0.28347 (15)0.1245 (3)0.0382 (6)
H22A0.33510.31110.07510.046*
H22B0.33380.31130.17320.046*
C230.43054 (16)0.27809 (16)0.1259 (3)0.0398 (7)
H23A0.44700.25110.07710.048*
H23B0.44580.25160.17560.048*
C240.46495 (17)0.35212 (16)0.1260 (3)0.0401 (7)
H24A0.44910.37810.07610.048*
H24B0.44730.37890.17440.048*
C250.54620 (17)0.35175 (17)0.1280 (4)0.0431 (8)
H25A0.56240.32720.17860.052*
H25B0.56430.32430.08020.052*
C260.57782 (17)0.42618 (17)0.1259 (4)0.0418 (7)
H26A0.56000.45310.17420.050*
H26B0.56030.45090.07590.050*
C270.65939 (18)0.42879 (18)0.1262 (4)0.0456 (7)
H27A0.67760.40180.07810.055*
H27B0.67720.40480.17650.055*
C280.68898 (19)0.50508 (18)0.1232 (4)0.0511 (8)
H28A0.67170.52850.07230.061*
H28B0.66950.53220.17050.061*
C290.7693 (2)0.5095 (2)0.1254 (4)0.0631 (10)
H29A0.78420.55930.11800.076*
H29B0.78930.48010.08110.076*
H29C0.78660.49190.17860.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0595 (3)0.0692 (3)0.0449 (2)0.0066 (3)0.0008 (2)0.0063 (2)
Br20.0848 (4)0.0898 (5)0.0442 (3)0.0012 (4)0.0047 (3)0.0042 (3)
C10.0282 (16)0.0282 (15)0.053 (2)0.0006 (13)0.0035 (18)0.0012 (15)
C20.038 (2)0.033 (2)0.055 (3)0.0050 (17)0.0029 (17)0.0065 (17)
C30.0231 (15)0.043 (2)0.0388 (19)0.0160 (14)0.0062 (15)0.0086 (15)
C40.0358 (18)0.0342 (18)0.054 (2)0.0047 (14)0.0036 (17)0.0118 (17)
C50.0344 (18)0.0273 (18)0.061 (2)0.0018 (14)0.0014 (17)0.0036 (16)
C60.0292 (17)0.0278 (16)0.050 (2)0.0023 (13)0.0043 (16)0.0011 (15)
C70.0314 (17)0.0331 (18)0.053 (2)0.0024 (14)0.0018 (16)0.0009 (16)
C80.053 (2)0.038 (2)0.055 (2)0.0047 (17)0.0041 (19)0.0034 (18)
C90.059 (3)0.056 (3)0.057 (3)0.000 (2)0.008 (2)0.018 (2)
C100.049 (2)0.043 (2)0.059 (2)0.0084 (18)0.007 (2)0.0047 (19)
C110.0284 (17)0.071 (3)0.030 (2)0.0043 (18)0.0022 (15)0.0034 (18)
C120.0317 (16)0.0307 (16)0.053 (2)0.0021 (13)0.0013 (18)0.0023 (15)
C130.0347 (15)0.0315 (14)0.0402 (16)0.0007 (11)0.0033 (18)0.0008 (18)
C140.0379 (16)0.0342 (15)0.0490 (17)0.0066 (12)0.003 (2)0.0019 (19)
C150.0336 (16)0.0403 (16)0.057 (2)0.0033 (12)0.002 (2)0.001 (2)
C160.0332 (16)0.0487 (18)0.0511 (19)0.0020 (13)0.002 (2)0.003 (2)
C170.0362 (17)0.0526 (19)0.0536 (19)0.0010 (14)0.003 (2)0.001 (2)
C180.0362 (17)0.0483 (18)0.055 (2)0.0026 (14)0.001 (2)0.003 (2)
C190.0363 (17)0.0497 (19)0.0504 (19)0.0037 (14)0.004 (2)0.002 (2)
C200.0375 (17)0.054 (2)0.066 (2)0.0005 (15)0.003 (2)0.009 (3)
C210.045 (2)0.055 (2)0.076 (3)0.0007 (16)0.008 (3)0.003 (3)
C220.0387 (16)0.0296 (14)0.0464 (17)0.0028 (12)0.003 (2)0.0026 (19)
C230.0389 (16)0.0312 (14)0.0494 (18)0.0012 (12)0.001 (2)0.0004 (19)
C240.0379 (16)0.0339 (15)0.0484 (18)0.0023 (12)0.004 (2)0.005 (2)
C250.0367 (16)0.0351 (15)0.057 (2)0.0017 (13)0.005 (2)0.000 (2)
C260.0366 (16)0.0363 (15)0.0526 (19)0.0024 (13)0.004 (2)0.004 (2)
C270.0407 (17)0.0455 (17)0.0505 (19)0.0032 (14)0.001 (2)0.007 (2)
C280.051 (2)0.0405 (17)0.062 (2)0.0077 (15)0.005 (2)0.007 (2)
C290.053 (2)0.061 (2)0.075 (3)0.0176 (18)0.002 (3)0.005 (3)
Geometric parameters (Å, º) top
Br1—C31.936 (4)C18—C191.519 (5)
Br2—C101.904 (5)C18—H18A0.9900
C1—C21.402 (5)C18—H18B0.9900
C1—C61.399 (5)C19—C201.522 (5)
C1—C131.506 (5)C19—H19A0.9900
C2—C31.360 (6)C19—H19B0.9900
C2—H20.9500C20—C211.505 (5)
C3—C41.381 (5)C20—H20A0.9900
C4—C51.378 (6)C20—H20B0.9900
C4—H40.9500C21—H21A0.9800
C5—C61.397 (5)C21—H21B0.9800
C5—H50.9500C21—H21C0.9800
C6—C71.452 (4)C22—C231.526 (4)
C7—C81.393 (6)C22—H22A0.9900
C7—C121.413 (5)C22—H22B0.9900
C8—C91.382 (7)C23—C241.527 (4)
C8—H80.9500C23—H23A0.9900
C9—C101.388 (7)C23—H23B0.9900
C9—H90.9500C24—C251.520 (4)
C10—C111.326 (6)C24—H24A0.9900
C11—C121.342 (5)C24—H24B0.9900
C11—H110.9500C25—C261.513 (4)
C12—C131.534 (5)C25—H25A0.9900
C13—C141.544 (4)C25—H25B0.9900
C13—C221.548 (4)C26—C271.526 (5)
C14—C151.516 (4)C26—H26A0.9900
C14—H14A0.9900C26—H26B0.9900
C14—H14B0.9900C27—C281.531 (5)
C15—C161.524 (5)C27—H27A0.9900
C15—H15A0.9900C27—H27B0.9900
C15—H15B0.9900C28—C291.504 (5)
C16—C171.517 (5)C28—H28A0.9900
C16—H16A0.9900C28—H28B0.9900
C16—H16B0.9900C29—H29A0.9800
C17—C181.526 (5)C29—H29B0.9800
C17—H17A0.9900C29—H29C0.9800
C17—H17B0.9900
C2—C1—C6120.4 (3)C19—C18—H18A109.1
C2—C1—C13127.8 (3)C19—C18—H18B109.1
C6—C1—C13111.8 (3)H18A—C18—H18B107.9
C1—C2—C3116.3 (3)C18—C19—C20113.4 (3)
C1—C2—H2121.8C18—C19—H19A108.9
C3—C2—H2121.8C18—C19—H19B108.9
Br1—C3—C2118.4 (3)C20—C19—H19A108.9
Br1—C3—C4116.2 (3)C20—C19—H19B108.9
C2—C3—C4125.4 (4)H19A—C19—H19B107.7
C3—C4—C5117.9 (4)C19—C20—C21113.1 (3)
C3—C4—H4121.0C19—C20—H20A109.0
C5—C4—H4121.0C19—C20—H20B109.0
C4—C5—C6119.5 (3)C21—C20—H20A109.0
C4—C5—H5120.3C21—C20—H20B109.0
C6—C5—H5120.3H20A—C20—H20B107.8
C1—C6—C5120.5 (4)C20—C21—H21A109.5
C1—C6—C7108.0 (3)C20—C21—H21B109.5
C5—C6—C7131.5 (4)C20—C21—H21C109.5
C6—C7—C8131.1 (4)H21A—C21—H21B109.5
C6—C7—C12109.4 (4)H21A—C21—H21C109.5
C8—C7—C12119.4 (4)H21B—C21—H21C109.5
C7—C8—C9119.3 (4)C13—C22—C23116.7 (2)
C7—C8—H8120.4C13—C22—H22A108.1
C9—C8—H8120.4C13—C22—H22B108.1
C8—C9—C10118.8 (4)C23—C22—H22A108.1
C8—C9—H9120.6C23—C22—H22B108.1
C10—C9—H9120.6H22A—C22—H22B107.3
Br2—C10—C9117.6 (4)C22—C23—C24111.1 (2)
Br2—C10—C11120.9 (3)C22—C23—H23A109.4
C9—C10—C11121.4 (4)C22—C23—H23B109.4
C10—C11—C12122.1 (4)C24—C23—H23A109.4
C10—C11—H11118.9C24—C23—H23B109.4
C12—C11—H11118.9H23A—C23—H23B108.0
C7—C12—C11118.9 (4)C23—C24—C25114.7 (3)
C7—C12—C13109.4 (3)C23—C24—H24A108.6
C11—C12—C13131.6 (3)C23—C24—H24B108.6
C1—C13—C12101.4 (2)C25—C24—H24A108.6
C1—C13—C14111.7 (3)C25—C24—H24B108.6
C12—C13—C14110.8 (3)H24A—C24—H24B107.6
C1—C13—C22113.0 (3)C24—C25—C26112.7 (3)
C12—C13—C22112.5 (3)C24—C25—H25A109.0
C14—C13—C22107.4 (2)C24—C25—H25B109.0
C13—C14—C15115.9 (2)C26—C25—H25A109.0
C13—C14—H14A108.3C26—C25—H25B109.0
C13—C14—H14B108.3H25A—C25—H25B107.8
C15—C14—H14A108.3C25—C26—C27114.8 (3)
C15—C14—H14B108.3C25—C26—H26A108.6
H14A—C14—H14B107.4C25—C26—H26B108.6
C14—C15—C16112.5 (3)C27—C26—H26A108.6
C14—C15—H15A109.1C27—C26—H26B108.6
C14—C15—H15B109.1H26A—C26—H26B107.5
C16—C15—H15A109.1C26—C27—C28113.0 (3)
C16—C15—H15B109.1C26—C27—H27A109.0
H15A—C15—H15B107.8C26—C27—H27B109.0
C15—C16—C17112.3 (3)C28—C27—H27A109.0
C15—C16—H16A109.1C28—C27—H27B109.0
C15—C16—H16B109.1H27A—C27—H27B107.8
C17—C16—H16A109.1C27—C28—C29114.3 (3)
C17—C16—H16B109.1C27—C28—H28A108.7
H16A—C16—H16B107.9C27—C28—H28B108.7
C16—C17—C18114.5 (3)C29—C28—H28A108.7
C16—C17—H17A108.6C29—C28—H28B108.7
C16—C17—H17B108.6H28A—C28—H28B107.6
C18—C17—H17A108.6C28—C29—H29A109.5
C18—C17—H17B108.6C28—C29—H29B109.5
H17A—C17—H17B107.6C28—C29—H29C109.5
C17—C18—C19112.4 (3)H29A—C29—H29B109.5
C17—C18—H18A109.1H29A—C29—H29C109.5
C17—C18—H18B109.1H29B—C29—H29C109.5
C6—C1—C2—C31.4 (5)C8—C9—C10—Br2178.7 (3)
C13—C1—C2—C3176.6 (3)C8—C9—C10—C110.2 (7)
C2—C1—C6—C50.5 (5)Br2—C10—C11—C12179.5 (3)
C2—C1—C6—C7178.8 (3)C9—C10—C11—C121.2 (7)
C13—C1—C6—C5177.8 (3)C10—C11—C12—C71.4 (6)
C13—C1—C6—C70.5 (4)C10—C11—C12—C13178.0 (4)
C2—C1—C13—C12178.1 (4)C7—C12—C13—C10.7 (3)
C2—C1—C13—C1460.0 (5)C7—C12—C13—C14119.4 (3)
C2—C1—C13—C2261.2 (5)C7—C12—C13—C22120.4 (3)
C6—C1—C13—C120.1 (3)C11—C12—C13—C1176.2 (5)
C6—C1—C13—C14118.1 (3)C11—C12—C13—C1457.4 (5)
C6—C1—C13—C22120.6 (3)C11—C12—C13—C2262.8 (5)
C1—C2—C3—Br1179.4 (3)C1—C13—C14—C1554.4 (5)
C1—C2—C3—C42.0 (6)C12—C13—C14—C1557.9 (5)
Br1—C3—C4—C5179.1 (3)C22—C13—C14—C15178.9 (4)
C2—C3—C4—C51.7 (6)C1—C13—C22—C2355.8 (5)
C3—C4—C5—C60.7 (5)C12—C13—C22—C2358.4 (5)
C4—C5—C6—C10.1 (5)C14—C13—C22—C23179.4 (4)
C4—C5—C6—C7178.0 (4)C13—C14—C15—C16178.3 (4)
C1—C6—C7—C8177.6 (4)C14—C15—C16—C17178.7 (4)
C1—C6—C7—C121.0 (5)C15—C16—C17—C18179.8 (5)
C5—C6—C7—C80.5 (8)C16—C17—C18—C19179.9 (5)
C5—C6—C7—C12177.1 (4)C17—C18—C19—C20177.5 (6)
C6—C7—C8—C9176.4 (4)C18—C19—C20—C21178.3 (5)
C12—C7—C8—C90.1 (6)C13—C22—C23—C24179.8 (4)
C6—C7—C12—C11176.3 (4)C22—C23—C24—C25179.6 (5)
C6—C7—C12—C131.0 (4)C23—C24—C25—C26178.6 (5)
C8—C7—C12—C110.8 (5)C24—C25—C26—C27178.9 (5)
C8—C7—C12—C13178.1 (3)C25—C26—C27—C28179.5 (5)
C7—C8—C9—C100.3 (7)C26—C27—C28—C29178.7 (5)
 

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