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In the crystal structure, the title compound, C23H33BN2, exhibits approximate Cs symmetry, with B-N bond lengths of 1.414 (2) and 1.419 (2) Å, consistent with B=N double bonds. This is also reflected by the trigonal planes around the B and butyl­amino N atoms, which are virtually coplanar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805019902/sg6020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805019902/sg6020Isup2.hkl
Contains datablock I

CCDC reference: 277780

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.054
  • wR factor = 0.123
  • Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT414_ALERT_2_C Short Intra D-H..H-X H1A .. H20C .. 1.96 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1A ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART-NT (Bruker, 2001); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: XP in SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: XP in SHELXTL.

(tert-butylamino)(diisopropylamino)(9-fluorenyl)borane top
Crystal data top
C23H33BN2F(000) = 760
Mr = 348.32Dx = 1.075 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9516 reflections
a = 9.2771 (5) Åθ = 2.5–25.4°
b = 16.0667 (9) ŵ = 0.06 mm1
c = 14.5453 (8) ÅT = 193 K
β = 97.034 (1)°Block, colourless
V = 2151.7 (2) Å30.35 × 0.25 × 0.21 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
4269 independent reflections
Radiation source: fine-focus sealed tube3774 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.042
φ and ω scansθmax = 26.1°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2002)
h = 1111
Tmin = 0.954, Tmax = 0.987k = 1919
35746 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0434P)2 + 0.798P]
where P = (Fo2 + 2Fc2)/3
4269 reflections(Δ/σ)max < 0.001
246 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.20 e Å3
Special details top

Experimental. 1H NMR (300 MHz, CD2Cl2, -30°C): δ = 0.05 (6H, d, 2xCH3iPr), 1.20 (6H, d, 2xCH3iPr), 1.44 (1H, m, 2xCHiPr), 1.46 (9H, s, CH3tBu), 2.87 (1H, m, 2xCHiPr), 3.36 (1H, s, BCH), 4.21 (1H, s, NH), 7.2–7.9 (8H, m, CHFlu). 13C NMR (75 MHz, CD2Cl2, -30°C): δ = 20.9, 24.3 (2x2xCH3iPr), 34.7 (3xCH3tBu), 43.2, 47.6 (2xCHiPr), 49.4 (quarternary CtBu), 120.7, 125.0, 125.9, 127.1 (4xCHFlu), 141.7, 150.1 (quarternary CFlu), BCH not observed due to quadrupolar 13C-11B coupling. 11B NMR (64 MHz, benzene-D6, 21°C): δ = 30.2. MS (EI+); m/z (%): 347 (3) [M±H], 333 (10) [M±Me], 183 (100) [M±C13H9], 165 (19) [C13H9+], 127 (33) [M±C13H8—C4H9].

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
N21.04367 (13)0.21834 (8)0.17667 (8)0.0316 (3)
N10.84448 (14)0.11867 (8)0.13706 (9)0.0336 (3)
C20.85304 (16)0.38845 (10)0.01802 (10)0.0331 (3)
C80.95969 (16)0.26124 (10)0.04424 (10)0.0318 (3)
C100.79696 (16)0.33086 (10)0.04049 (10)0.0323 (3)
C41.03492 (17)0.37259 (11)0.13948 (11)0.0395 (4)
H4A1.03010.42910.15890.047*
C90.85763 (16)0.24511 (9)0.02682 (10)0.0305 (3)
H9A0.77550.21180.00560.037*
C71.04892 (18)0.20607 (11)0.08314 (11)0.0405 (4)
H7A1.05430.14950.06410.049*
C30.95359 (16)0.34486 (10)0.07148 (10)0.0328 (3)
C211.11618 (18)0.29824 (10)0.16332 (11)0.0406 (4)
H21A1.06070.32520.10790.049*
C181.11309 (17)0.16973 (10)0.25653 (10)0.0346 (3)
H18A1.19990.20280.28270.042*
C110.69490 (17)0.35559 (11)0.09674 (11)0.0401 (4)
H11A0.65660.31680.13660.048*
C140.72789 (17)0.06898 (10)0.08486 (11)0.0366 (4)
C51.12271 (18)0.31671 (12)0.17827 (11)0.0452 (4)
H5A1.17870.33490.22490.054*
C61.1302 (2)0.23454 (12)0.15018 (12)0.0470 (4)
H6A1.19210.19710.17730.056*
C201.01891 (19)0.16146 (12)0.33499 (11)0.0452 (4)
H20A0.98440.21660.35100.068*
H20B1.07640.13690.38930.068*
H20C0.93550.12550.31500.068*
C120.64937 (19)0.43764 (12)0.09409 (12)0.0471 (4)
H12A0.57850.45500.13200.057*
C10.80839 (18)0.47113 (10)0.01876 (12)0.0405 (4)
H1B0.84820.51070.05710.049*
B10.91893 (17)0.19214 (10)0.11748 (11)0.0282 (3)
C160.7737 (2)0.03897 (11)0.00704 (12)0.0466 (4)
H16A0.86240.00560.00500.070*
H16B0.79200.08710.04530.070*
H16C0.69590.00500.03970.070*
C130.70581 (19)0.49480 (11)0.03689 (12)0.0470 (4)
H13A0.67340.55090.03600.056*
C150.58450 (18)0.11697 (12)0.06855 (13)0.0480 (4)
H15A0.55750.13630.12800.072*
H15B0.50820.08040.03860.072*
H15C0.59600.16500.02850.072*
C191.1723 (2)0.08647 (11)0.22785 (13)0.0490 (4)
H19A1.23850.09580.18130.073*
H19B1.09170.05100.20170.073*
H19C1.22490.05910.28220.073*
C170.7053 (2)0.00683 (12)0.14449 (13)0.0534 (5)
H17A0.79650.03800.15650.080*
H17B0.63020.04270.11190.080*
H17D0.67470.01140.20340.080*
C231.1080 (3)0.35728 (12)0.24438 (14)0.0627 (6)
H23A1.00620.36560.25380.094*
H23D1.15130.41090.23100.094*
H23B1.16120.33330.30060.094*
C221.2711 (2)0.28777 (14)0.14127 (16)0.0633 (6)
H22D1.27180.25080.08770.095*
H22A1.33080.26350.19480.095*
H22B1.31060.34220.12700.095*
H1A0.8795 (19)0.0913 (11)0.1863 (12)0.040 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N20.0307 (6)0.0324 (7)0.0301 (6)0.0016 (5)0.0028 (5)0.0023 (5)
N10.0358 (7)0.0361 (7)0.0268 (6)0.0057 (5)0.0045 (5)0.0043 (5)
C20.0290 (7)0.0366 (8)0.0308 (7)0.0022 (6)0.0078 (6)0.0006 (6)
C80.0316 (8)0.0368 (8)0.0255 (7)0.0036 (6)0.0025 (6)0.0017 (6)
C100.0282 (7)0.0389 (8)0.0273 (7)0.0004 (6)0.0066 (6)0.0005 (6)
C40.0375 (9)0.0439 (9)0.0356 (8)0.0083 (7)0.0018 (7)0.0091 (7)
C90.0288 (7)0.0345 (8)0.0271 (7)0.0032 (6)0.0014 (6)0.0008 (6)
C70.0461 (9)0.0389 (9)0.0368 (8)0.0022 (7)0.0058 (7)0.0019 (7)
C30.0298 (7)0.0374 (8)0.0289 (7)0.0048 (6)0.0058 (6)0.0026 (6)
C210.0387 (9)0.0397 (9)0.0404 (9)0.0096 (7)0.0079 (7)0.0052 (7)
C180.0321 (8)0.0384 (8)0.0307 (7)0.0008 (6)0.0066 (6)0.0009 (6)
C110.0352 (8)0.0511 (10)0.0330 (8)0.0010 (7)0.0008 (7)0.0002 (7)
C140.0377 (8)0.0383 (9)0.0334 (8)0.0121 (7)0.0027 (6)0.0038 (7)
C50.0397 (9)0.0619 (12)0.0346 (8)0.0067 (8)0.0071 (7)0.0079 (8)
C60.0456 (10)0.0563 (11)0.0403 (9)0.0053 (8)0.0103 (8)0.0008 (8)
C200.0447 (10)0.0578 (11)0.0308 (8)0.0026 (8)0.0046 (7)0.0041 (8)
C120.0409 (9)0.0561 (11)0.0430 (9)0.0083 (8)0.0002 (8)0.0111 (8)
C10.0394 (9)0.0361 (9)0.0429 (9)0.0037 (7)0.0078 (7)0.0014 (7)
B10.0277 (8)0.0314 (8)0.0252 (8)0.0015 (7)0.0031 (6)0.0013 (6)
C160.0520 (10)0.0474 (10)0.0409 (9)0.0126 (8)0.0079 (8)0.0098 (8)
C130.0457 (10)0.0392 (9)0.0523 (10)0.0085 (8)0.0097 (8)0.0094 (8)
C150.0341 (9)0.0638 (12)0.0454 (10)0.0117 (8)0.0018 (7)0.0053 (9)
C190.0488 (10)0.0490 (11)0.0459 (10)0.0140 (8)0.0065 (8)0.0005 (8)
C170.0662 (12)0.0461 (10)0.0473 (10)0.0225 (9)0.0052 (9)0.0000 (8)
C230.0818 (15)0.0403 (10)0.0611 (12)0.0133 (10)0.0107 (11)0.0070 (9)
C220.0404 (10)0.0775 (15)0.0700 (13)0.0183 (10)0.0005 (9)0.0171 (11)
Geometric parameters (Å, º) top
N2—B11.419 (2)C14—C151.531 (2)
N2—C211.473 (2)C5—C61.381 (3)
N2—C181.4801 (18)C5—H5A0.9500
N1—B11.414 (2)C6—H6A0.9500
N1—C141.4773 (19)C20—H20A0.9800
N1—H1A0.869 (18)C20—H20B0.9800
C2—C11.391 (2)C20—H20C0.9800
C2—C101.400 (2)C12—C131.384 (3)
C2—C31.464 (2)C12—H12A0.9500
C8—C71.380 (2)C1—C131.376 (2)
C8—C31.400 (2)C1—H1B0.9500
C8—C91.507 (2)C16—H16A0.9800
C10—C111.383 (2)C16—H16B0.9800
C10—C91.511 (2)C16—H16C0.9800
C4—C51.379 (2)C13—H13A0.9500
C4—C31.389 (2)C15—H15A0.9800
C4—H4A0.9500C15—H15B0.9800
C9—B11.613 (2)C15—H15C0.9800
C9—H9A1.0000C19—H19A0.9800
C7—C61.382 (2)C19—H19B0.9800
C7—H7A0.9500C19—H19C0.9800
C21—C221.520 (3)C17—H17A0.9800
C21—C231.522 (3)C17—H17B0.9800
C21—H21A1.0000C17—H17D0.9800
C18—C191.524 (2)C23—H23A0.9800
C18—C201.526 (2)C23—H23D0.9800
C18—H18A1.0000C23—H23B0.9800
C11—C121.383 (2)C22—H22D0.9800
C11—H11A0.9500C22—H22A0.9800
C14—C171.525 (2)C22—H22B0.9800
C14—C161.529 (2)
B1—N2—C21122.01 (12)C7—C6—H6A119.6
B1—N2—C18124.31 (12)C18—C20—H20A109.5
C21—N2—C18113.67 (11)C18—C20—H20B109.5
B1—N1—C14133.83 (13)H20A—C20—H20B109.5
B1—N1—H1A116.5 (11)C18—C20—H20C109.5
C14—N1—H1A109.0 (12)H20A—C20—H20C109.5
C1—C2—C10120.22 (15)H20B—C20—H20C109.5
C1—C2—C3131.39 (15)C11—C12—C13120.81 (16)
C10—C2—C3108.37 (13)C11—C12—H12A119.6
C7—C8—C3120.38 (14)C13—C12—H12A119.6
C7—C8—C9129.00 (14)C13—C1—C2119.08 (16)
C3—C8—C9110.61 (13)C13—C1—H1B120.5
C11—C10—C2120.14 (15)C2—C1—H1B120.5
C11—C10—C9129.26 (14)N1—B1—N2120.51 (13)
C2—C10—C9110.52 (13)N1—B1—C9118.23 (13)
C5—C4—C3118.83 (16)N2—B1—C9121.26 (13)
C5—C4—H4A120.6C14—C16—H16A109.5
C3—C4—H4A120.6C14—C16—H16B109.5
C8—C9—C10102.07 (12)H16A—C16—H16B109.5
C8—C9—B1117.58 (12)C14—C16—H16C109.5
C10—C9—B1118.24 (12)H16A—C16—H16C109.5
C8—C9—H9A106.0H16B—C16—H16C109.5
C10—C9—H9A106.0C1—C13—C12120.65 (16)
B1—C9—H9A106.0C1—C13—H13A119.7
C8—C7—C6118.90 (16)C12—C13—H13A119.7
C8—C7—H7A120.5C14—C15—H15A109.5
C6—C7—H7A120.5C14—C15—H15B109.5
C4—C3—C8120.19 (15)H15A—C15—H15B109.5
C4—C3—C2131.44 (15)C14—C15—H15C109.5
C8—C3—C2108.37 (13)H15A—C15—H15C109.5
N2—C21—C22112.97 (15)H15B—C15—H15C109.5
N2—C21—C23111.96 (14)C18—C19—H19A109.5
C22—C21—C23111.75 (16)C18—C19—H19B109.5
N2—C21—H21A106.6H19A—C19—H19B109.5
C22—C21—H21A106.6C18—C19—H19C109.5
C23—C21—H21A106.6H19A—C19—H19C109.5
N2—C18—C19112.66 (12)H19B—C19—H19C109.5
N2—C18—C20113.52 (12)C14—C17—H17A109.5
C19—C18—C20112.78 (14)C14—C17—H17B109.5
N2—C18—H18A105.7H17A—C17—H17B109.5
C19—C18—H18A105.7C14—C17—H17D109.5
C20—C18—H18A105.7H17A—C17—H17D109.5
C10—C11—C12119.08 (16)H17B—C17—H17D109.5
C10—C11—H11A120.5C21—C23—H23A109.5
C12—C11—H11A120.5C21—C23—H23D109.5
N1—C14—C17106.40 (13)H23A—C23—H23D109.5
N1—C14—C16110.82 (13)C21—C23—H23B109.5
C17—C14—C16108.52 (14)H23A—C23—H23B109.5
N1—C14—C15112.03 (13)H23D—C23—H23B109.5
C17—C14—C15108.25 (14)C21—C22—H22D109.5
C16—C14—C15110.64 (14)C21—C22—H22A109.5
C4—C5—C6120.83 (15)H22D—C22—H22A109.5
C4—C5—H5A119.6C21—C22—H22B109.5
C6—C5—H5A119.6H22D—C22—H22B109.5
C5—C6—C7120.86 (17)H22A—C22—H22B109.5
C5—C6—H6A119.6
C1—C2—C10—C111.1 (2)B1—N2—C18—C1962.75 (19)
C3—C2—C10—C11177.88 (13)C21—N2—C18—C19117.36 (15)
C1—C2—C10—C9178.18 (13)B1—N2—C18—C2066.98 (19)
C3—C2—C10—C90.83 (16)C21—N2—C18—C20112.91 (15)
C7—C8—C9—C10178.77 (15)C2—C10—C11—C120.1 (2)
C3—C8—C9—C102.53 (15)C9—C10—C11—C12176.35 (15)
C7—C8—C9—B147.6 (2)B1—N1—C14—C17176.15 (17)
C3—C8—C9—B1133.65 (13)B1—N1—C14—C1658.4 (2)
C11—C10—C9—C8178.71 (14)B1—N1—C14—C1565.7 (2)
C2—C10—C9—C82.00 (15)C3—C4—C5—C60.1 (2)
C11—C10—C9—B150.6 (2)C4—C5—C6—C70.6 (3)
C2—C10—C9—B1132.72 (13)C8—C7—C6—C50.1 (3)
C3—C8—C7—C60.9 (2)C10—C11—C12—C130.7 (2)
C9—C8—C7—C6177.69 (15)C10—C2—C1—C131.7 (2)
C5—C4—C3—C80.9 (2)C3—C2—C1—C13177.04 (15)
C5—C4—C3—C2179.63 (15)C14—N1—B1—N2169.91 (15)
C7—C8—C3—C41.5 (2)C14—N1—B1—C910.4 (2)
C9—C8—C3—C4177.38 (13)C21—N2—B1—N1174.37 (14)
C7—C8—C3—C2178.99 (13)C18—N2—B1—N15.5 (2)
C9—C8—C3—C22.17 (16)C21—N2—B1—C95.3 (2)
C1—C2—C3—C40.2 (3)C18—N2—B1—C9174.84 (13)
C10—C2—C3—C4178.65 (15)C8—C9—B1—N1123.05 (15)
C1—C2—C3—C8179.69 (15)C10—C9—B1—N1113.69 (15)
C10—C2—C3—C80.83 (16)C8—C9—B1—N257.29 (19)
B1—N2—C21—C22116.99 (17)C10—C9—B1—N265.97 (18)
C18—N2—C21—C2263.12 (18)C2—C1—C13—C121.1 (2)
B1—N2—C21—C23115.79 (17)C11—C12—C13—C10.1 (3)
C18—N2—C21—C2364.10 (18)
 

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