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The title compound, C26H30B10P2, was synthesized by the reaction of 1,2-dilithio­carborane with diphenyl­choro­phos­phine in diethyl ether. The mol­ecular symmetry of the mol­ecule deviates from C2v because of the different mutual orientations of the phenyl groups. The two P atoms of the -PPh2 groups and two cage C atoms are almost coplanar, with a P-C-C-P torsion angle of 10.6 (3)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805042510/lh6572sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805042510/lh6572Isup2.hkl
Contains datablock I

CCDC reference: 289021

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.049
  • wR factor = 0.145
  • Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT320_ALERT_2_C Check Hybridisation of C1 in Main Residue . ? PLAT320_ALERT_2_C Check Hybridisation of C2 in Main Residue . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT367_ALERT_2_C Long? C(sp?)-C(sp?) Bond C1 - C2 ... 1.70 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 1 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 (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1,2-Diphenylphosphino-1,2-dicarba-closo-dodecaborane top
Crystal data top
C26H30B10P2F(000) = 1064
Mr = 512.54Dx = 1.218 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 4735 reflections
a = 16.315 (6) Åθ = 2.3–26.3°
b = 10.387 (4) ŵ = 0.17 mm1
c = 17.768 (6) ÅT = 298 K
β = 111.845 (5)°Block, white
V = 2795.0 (17) Å30.43 × 0.41 × 0.40 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6721 independent reflections
Radiation source: fine-focus sealed tube4367 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 28.4°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2121
Tmin = 0.930, Tmax = 0.934k = 1213
17791 measured reflectionsl = 1123
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.065P)2 + 1.0346P]
where P = (Fo2 + 2Fc2)/3
6721 reflections(Δ/σ)max = 0.001
343 parametersΔρmax = 0.58 e Å3
3 restraintsΔρmin = 0.33 e Å3
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
P10.03941 (5)0.84048 (8)0.23665 (5)0.0329 (2)
P20.03034 (6)1.08544 (8)0.35597 (5)0.0323 (2)
B60.0029 (3)1.0920 (4)0.1748 (2)0.0332 (8)
H30.07281.11560.16030.040*
B70.0821 (3)1.2093 (4)0.2122 (2)0.0385 (9)
H40.06781.31040.22110.046*
B80.1774 (3)1.1308 (4)0.2801 (2)0.0384 (9)
H50.22461.18070.33310.046*
B30.1507 (2)0.9656 (4)0.2841 (2)0.0339 (8)
H60.17940.90850.33990.041*
B40.1270 (2)0.8981 (4)0.1854 (2)0.0365 (9)
H70.14150.79700.17680.044*
B50.0312 (3)0.9769 (4)0.1177 (2)0.0369 (9)
H80.01660.92680.06510.044*
B110.0557 (3)1.1435 (4)0.1144 (2)0.0404 (9)
H90.02381.20170.05950.048*
B120.1685 (3)1.1654 (4)0.1799 (3)0.0436 (10)
H100.21061.23800.16710.052*
B90.2116 (3)1.0149 (4)0.2244 (3)0.0425 (9)
H110.28160.98930.24120.051*
B100.1376 (3)1.0232 (4)0.1216 (3)0.0436 (10)
H120.15941.00380.07110.052*
C20.0734 (2)1.0839 (3)0.27146 (18)0.0299 (7)
C10.04424 (19)0.9464 (3)0.21637 (18)0.0290 (7)
C30.0221 (2)0.7467 (3)0.3271 (2)0.0336 (7)
C40.1008 (2)0.6802 (3)0.3427 (2)0.0387 (8)
H130.12830.68260.30520.046*
C50.1384 (3)0.6105 (4)0.4138 (2)0.0498 (10)
H140.19080.56590.42350.060*
C60.0994 (3)0.6066 (4)0.4698 (2)0.0593 (11)
H150.12510.55940.51730.071*
C70.0223 (3)0.6722 (4)0.4557 (3)0.0609 (12)
H160.00420.66970.49390.073*
C80.0165 (3)0.7424 (3)0.3848 (2)0.0460 (9)
H170.06880.78680.37590.055*
C90.0660 (2)0.7258 (3)0.1529 (2)0.0373 (8)
C100.0212 (3)0.6125 (4)0.1512 (2)0.0543 (10)
H180.02810.58910.19610.065*
C110.0492 (3)0.5341 (4)0.0832 (3)0.0668 (12)
H190.01830.45910.08270.080*
C120.1221 (3)0.5663 (5)0.0167 (3)0.0684 (13)
H200.14040.51340.02880.082*
C130.1678 (3)0.6754 (5)0.0172 (3)0.0615 (12)
H210.21730.69710.02800.074*
C140.1409 (2)0.7541 (4)0.0846 (2)0.0473 (9)
H220.17340.82770.08460.057*
C150.0540 (2)1.2110 (3)0.32898 (19)0.0353 (7)
C160.0449 (2)1.3426 (4)0.3204 (2)0.0461 (9)
H230.00971.37620.32520.055*
C170.1165 (3)1.4240 (4)0.3047 (2)0.0553 (10)
H240.10971.51190.29890.066*
C180.1974 (3)1.3766 (5)0.2976 (2)0.0575 (11)
H250.24491.43210.28790.069*
C190.2077 (3)1.2475 (5)0.3048 (3)0.0626 (12)
H260.26261.21470.29930.075*
C200.1366 (2)1.1652 (4)0.3202 (2)0.0484 (9)
H270.14451.07730.32460.058*
C210.1235 (2)1.1449 (3)0.44296 (19)0.0349 (7)
C220.1647 (3)1.2636 (4)0.4516 (2)0.0519 (10)
H280.14521.32310.40960.062*
C230.2347 (3)1.2944 (4)0.5224 (3)0.0600 (11)
H290.26181.37450.52760.072*
C240.2644 (3)1.2073 (5)0.5847 (2)0.0590 (11)
H300.31111.22860.63230.071*
C250.2253 (3)1.0893 (5)0.5767 (2)0.0619 (12)
H310.24611.02960.61860.074*
C260.1549 (3)1.0581 (4)0.5067 (2)0.0479 (9)
H320.12810.97800.50230.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0288 (4)0.0333 (5)0.0376 (5)0.0017 (3)0.0134 (4)0.0012 (4)
P20.0371 (5)0.0305 (4)0.0309 (4)0.0032 (3)0.0146 (4)0.0019 (3)
B60.0350 (19)0.0335 (19)0.0283 (18)0.0033 (15)0.0086 (16)0.0034 (15)
B70.047 (2)0.0313 (19)0.040 (2)0.0029 (17)0.0196 (19)0.0039 (16)
B80.034 (2)0.041 (2)0.042 (2)0.0090 (16)0.0155 (18)0.0009 (17)
B30.0263 (18)0.037 (2)0.038 (2)0.0013 (15)0.0114 (16)0.0042 (16)
B40.035 (2)0.039 (2)0.041 (2)0.0014 (16)0.0201 (18)0.0027 (17)
B50.040 (2)0.043 (2)0.0301 (19)0.0017 (17)0.0165 (17)0.0002 (16)
B110.047 (2)0.043 (2)0.034 (2)0.0012 (18)0.0173 (18)0.0065 (17)
B120.047 (2)0.044 (2)0.047 (2)0.0074 (19)0.025 (2)0.0021 (18)
B90.034 (2)0.048 (2)0.048 (2)0.0031 (18)0.0182 (19)0.0013 (19)
B100.045 (2)0.052 (3)0.041 (2)0.0044 (19)0.025 (2)0.0027 (19)
C20.0318 (16)0.0277 (15)0.0298 (16)0.0026 (13)0.0109 (13)0.0006 (12)
C10.0278 (15)0.0304 (16)0.0288 (16)0.0010 (12)0.0106 (13)0.0019 (12)
C30.0391 (18)0.0290 (16)0.0350 (17)0.0062 (13)0.0165 (15)0.0013 (13)
C40.0404 (19)0.0372 (18)0.0395 (19)0.0025 (15)0.0160 (16)0.0028 (15)
C50.055 (2)0.041 (2)0.047 (2)0.0015 (17)0.0107 (19)0.0067 (16)
C60.085 (3)0.051 (2)0.037 (2)0.005 (2)0.018 (2)0.0073 (18)
C70.095 (4)0.055 (3)0.048 (2)0.009 (2)0.043 (2)0.0004 (19)
C80.060 (2)0.039 (2)0.049 (2)0.0046 (17)0.0323 (19)0.0052 (17)
C90.0358 (18)0.0368 (18)0.0394 (19)0.0081 (14)0.0142 (15)0.0035 (14)
C100.059 (3)0.049 (2)0.048 (2)0.0050 (19)0.012 (2)0.0082 (18)
C110.084 (3)0.050 (3)0.066 (3)0.001 (2)0.026 (3)0.017 (2)
C120.085 (3)0.069 (3)0.049 (3)0.022 (3)0.022 (2)0.022 (2)
C130.061 (3)0.069 (3)0.044 (2)0.015 (2)0.006 (2)0.005 (2)
C140.043 (2)0.048 (2)0.046 (2)0.0061 (17)0.0100 (17)0.0010 (17)
C150.0384 (18)0.0399 (18)0.0286 (17)0.0012 (14)0.0139 (14)0.0054 (14)
C160.044 (2)0.044 (2)0.050 (2)0.0010 (16)0.0172 (18)0.0043 (17)
C170.065 (3)0.044 (2)0.053 (2)0.011 (2)0.017 (2)0.0022 (18)
C180.055 (3)0.068 (3)0.050 (2)0.023 (2)0.020 (2)0.005 (2)
C190.040 (2)0.078 (3)0.074 (3)0.004 (2)0.026 (2)0.005 (2)
C200.043 (2)0.052 (2)0.054 (2)0.0033 (17)0.0221 (19)0.0011 (18)
C210.0402 (18)0.0360 (18)0.0298 (16)0.0007 (14)0.0145 (14)0.0024 (13)
C220.058 (2)0.040 (2)0.043 (2)0.0051 (18)0.0029 (18)0.0045 (16)
C230.063 (3)0.049 (2)0.053 (3)0.017 (2)0.004 (2)0.0060 (19)
C240.054 (2)0.076 (3)0.037 (2)0.012 (2)0.0054 (19)0.001 (2)
C250.057 (3)0.074 (3)0.042 (2)0.008 (2)0.005 (2)0.020 (2)
C260.048 (2)0.052 (2)0.041 (2)0.0039 (17)0.0144 (18)0.0095 (17)
Geometric parameters (Å, º) top
P1—C31.827 (3)C2—C11.697 (4)
P1—C91.828 (3)C3—C81.390 (5)
P1—C11.889 (3)C3—C41.393 (5)
P2—C211.826 (3)C4—C51.385 (5)
P2—C151.826 (3)C4—H130.9300
P2—C21.880 (3)C5—C61.368 (6)
B6—C21.708 (5)C5—H140.9300
B6—C11.732 (5)C6—C71.368 (6)
B6—B111.763 (5)C6—H150.9300
B6—B71.779 (5)C7—C81.388 (6)
B6—B51.783 (5)C7—H160.9300
B6—H31.1000C8—H170.9300
B7—C21.714 (5)C9—C101.392 (5)
B7—B111.764 (6)C9—C141.396 (5)
B7—B121.767 (6)C10—C111.386 (6)
B7—B81.772 (6)C10—H180.9300
B7—H41.1000C11—C121.369 (7)
B8—C21.716 (5)C11—H190.9300
B8—B121.768 (6)C12—C131.358 (7)
B8—B91.775 (6)C12—H200.9300
B8—B31.779 (5)C13—C141.380 (6)
B8—H51.1000C13—H210.9300
B3—C21.714 (5)C14—H220.9300
B3—C11.717 (5)C15—C201.381 (5)
B3—B91.778 (5)C15—C161.390 (5)
B3—B41.792 (6)C16—C171.385 (5)
B3—H61.1000C16—H230.9300
B4—C11.711 (5)C17—C181.369 (6)
B4—B91.774 (6)C17—H240.9300
B4—B101.775 (6)C18—C191.363 (6)
B4—B51.778 (6)C18—H250.9300
B4—H71.1000C19—C201.385 (6)
B5—C11.714 (5)C19—H260.9300
B5—B101.778 (6)C20—H270.9300
B5—B111.782 (6)C21—C221.386 (5)
B5—H81.1000C21—C261.388 (5)
B11—B121.789 (6)C22—C231.385 (5)
B11—B101.799 (6)C22—H280.9300
B11—H91.1000C23—C241.371 (6)
B12—B101.767 (6)C23—H290.9300
B12—B91.776 (6)C24—C251.365 (6)
B12—H101.1000C24—H300.9300
B9—B101.779 (6)C25—C261.381 (5)
B9—H111.1000C25—H310.9300
B10—H121.1000C26—H320.9300
C3—P1—C9104.75 (16)B4—B9—B360.6 (2)
C3—P1—C1106.20 (14)B8—B9—B360.1 (2)
C9—P1—C1101.17 (14)B12—B9—B3107.6 (3)
C21—P2—C15106.83 (15)B4—B9—B1060.0 (2)
C21—P2—C2103.77 (15)B8—B9—B10107.8 (3)
C15—P2—C2105.40 (14)B12—B9—B1059.6 (2)
C2—B6—C159.10 (18)B3—B9—B10108.1 (3)
C2—B6—B11105.6 (3)B4—B9—H11121.3
C1—B6—B11105.7 (3)B8—B9—H11121.6
C2—B6—B758.8 (2)B12—B9—H11122.2
C1—B6—B7106.2 (3)B3—B9—H11121.6
B11—B6—B759.7 (2)B10—B9—H11122.0
C2—B6—B5105.9 (3)B12—B10—B4108.2 (3)
C1—B6—B558.4 (2)B12—B10—B5108.1 (3)
B11—B6—B560.3 (2)B4—B10—B560.1 (2)
B7—B6—B5107.9 (3)B12—B10—B960.1 (2)
C2—B6—H3123.4B4—B10—B959.9 (2)
C1—B6—H3123.4B5—B10—B9107.8 (3)
B11—B6—H3122.7B12—B10—B1160.2 (2)
B7—B6—H3122.1B4—B10—B11107.9 (3)
B5—B6—H3122.1B5—B10—B1159.7 (2)
C2—B7—B11105.4 (3)B9—B10—B11108.0 (3)
C2—B7—B12105.2 (3)B12—B10—H12121.5
B11—B7—B1260.9 (2)B4—B10—H12121.7
C2—B7—B858.9 (2)B5—B10—H12121.8
B11—B7—B8108.9 (3)B9—B10—H12121.8
B12—B7—B860.0 (2)B11—B10—H12121.8
C2—B7—B658.5 (2)C1—C2—B661.15 (19)
B11—B7—B659.7 (2)C1—C2—B7110.8 (2)
B12—B7—B6107.9 (3)B6—C2—B762.7 (2)
B8—B7—B6107.6 (3)C1—C2—B360.44 (19)
C2—B7—H4124.4B6—C2—B3113.1 (2)
B11—B7—H4121.7B7—C2—B3113.6 (3)
B12—B7—H4122.1C1—C2—B8110.3 (2)
B8—B7—H4121.3B6—C2—B8113.7 (3)
B6—B7—H4122.0B7—C2—B862.2 (2)
C2—B8—B12105.1 (3)B3—C2—B862.5 (2)
C2—B8—B758.8 (2)C1—C2—P2111.07 (19)
B12—B8—B759.9 (2)B6—C2—P2117.0 (2)
C2—B8—B9105.3 (3)B7—C2—P2128.7 (2)
B12—B8—B960.2 (2)B3—C2—P2112.1 (2)
B7—B8—B9108.1 (3)B8—C2—P2125.3 (2)
C2—B8—B358.73 (19)C2—C1—B4110.3 (2)
B12—B8—B3107.9 (3)C2—C1—B5109.6 (2)
B7—B8—B3107.8 (3)B4—C1—B562.5 (2)
B9—B8—B360.0 (2)C2—C1—B360.29 (19)
C2—B8—H5124.4B4—C1—B363.0 (2)
B12—B8—H5122.3B5—C1—B3113.8 (2)
B7—B8—H5121.6C2—C1—B659.75 (19)
B9—B8—H5122.1B4—C1—B6113.4 (3)
B3—B8—H5121.7B5—C1—B662.3 (2)
C2—B3—C159.27 (18)B3—C1—B6111.7 (2)
C2—B3—B9105.2 (3)C2—C1—P1116.6 (2)
C1—B3—B9105.0 (3)B4—C1—P1127.0 (2)
C2—B3—B858.8 (2)B5—C1—P1118.6 (2)
C1—B3—B8106.4 (3)B3—C1—P1123.2 (2)
B9—B3—B859.9 (2)B6—C1—P1110.7 (2)
C2—B3—B4105.8 (3)C8—C3—C4118.3 (3)
C1—B3—B458.3 (2)C8—C3—P1114.5 (3)
B9—B3—B459.6 (2)C4—C3—P1127.1 (3)
B8—B3—B4107.8 (3)C5—C4—C3120.2 (3)
C2—B3—H6123.4C5—C4—H13119.9
C1—B3—H6123.4C3—C4—H13119.9
B9—B3—H6123.2C6—C5—C4120.7 (4)
B8—B3—H6121.9C6—C5—H14119.6
B4—B3—H6122.4C4—C5—H14119.6
C1—B4—B9105.4 (3)C5—C6—C7119.8 (4)
C1—B4—B10105.4 (3)C5—C6—H15120.1
B9—B4—B1060.2 (2)C7—C6—H15120.1
C1—B4—B558.8 (2)C6—C7—C8120.3 (4)
B9—B4—B5108.0 (3)C6—C7—H16119.8
B10—B4—B560.0 (2)C8—C7—H16119.8
C1—B4—B358.64 (19)C7—C8—C3120.5 (4)
B9—B4—B359.8 (2)C7—C8—H17119.7
B10—B4—B3107.6 (3)C3—C8—H17119.7
B5—B4—B3107.3 (3)C10—C9—C14117.1 (3)
C1—B4—H7124.2C10—C9—P1127.0 (3)
B9—B4—H7122.1C14—C9—P1115.8 (3)
B10—B4—H7122.2C11—C10—C9120.7 (4)
B5—B4—H7121.7C11—C10—H18119.7
B3—B4—H7122.1C9—C10—H18119.7
C1—B5—B10105.2 (3)C12—C11—C10120.5 (4)
C1—B5—B458.6 (2)C12—C11—H19119.7
B10—B5—B459.9 (2)C10—C11—H19119.7
C1—B5—B11105.6 (3)C13—C12—C11120.1 (4)
B10—B5—B1160.7 (2)C13—C12—H20120.0
B4—B5—B11108.6 (3)C11—C12—H20120.0
C1—B5—B659.31 (19)C12—C13—C14120.1 (4)
B10—B5—B6107.6 (3)C12—C13—H21120.0
B4—B5—B6107.8 (3)C14—C13—H21120.0
B11—B5—B659.3 (2)C13—C14—C9121.5 (4)
C1—B5—H8124.1C13—C14—H22119.2
B10—B5—H8122.2C9—C14—H22119.2
B4—B5—H8121.5C20—C15—C16117.8 (3)
B11—B5—H8121.9C20—C15—P2113.1 (3)
B6—B5—H8121.9C16—C15—P2129.1 (3)
B6—B11—B760.6 (2)C17—C16—C15120.4 (4)
B6—B11—B560.4 (2)C17—C16—H23119.8
B7—B11—B5108.6 (3)C15—C16—H23119.8
B6—B11—B12107.6 (3)C18—C17—C16120.8 (4)
B7—B11—B1259.6 (2)C18—C17—H24119.6
B5—B11—B12106.9 (3)C16—C17—H24119.6
B6—B11—B10107.6 (3)C19—C18—C17119.6 (4)
B7—B11—B10107.2 (3)C19—C18—H25120.2
B5—B11—B1059.5 (2)C17—C18—H25120.2
B12—B11—B1059.0 (2)C18—C19—C20120.2 (4)
B6—B11—H9121.5C18—C19—H26119.9
B7—B11—H9121.5C20—C19—H26119.9
B5—B11—H9121.7C15—C20—C19121.3 (4)
B12—B11—H9122.6C15—C20—H27119.3
B10—B11—H9122.5C19—C20—H27119.3
B7—B12—B10108.5 (3)C22—C21—C26118.1 (3)
B7—B12—B860.2 (2)C22—C21—P2127.7 (3)
B10—B12—B8108.6 (3)C26—C21—P2114.2 (3)
B7—B12—B9108.3 (3)C23—C22—C21120.6 (4)
B10—B12—B960.3 (2)C23—C22—H28119.7
B8—B12—B960.1 (2)C21—C22—H28119.7
B7—B12—B1159.5 (2)C24—C23—C22120.3 (4)
B10—B12—B1160.8 (2)C24—C23—H29119.8
B8—B12—B11107.9 (3)C22—C23—H29119.8
B9—B12—B11108.6 (3)C25—C24—C23119.8 (4)
B7—B12—H10121.7C25—C24—H30120.1
B10—B12—H10121.1C23—C24—H30120.1
B8—B12—H10121.6C24—C25—C26120.3 (4)
B9—B12—H10121.4C24—C25—H31119.9
B11—B12—H10121.6C26—C25—H31119.9
B4—B9—B8108.7 (3)C25—C26—C21120.9 (4)
B4—B9—B12107.9 (3)C25—C26—H32119.6
B8—B9—B1259.7 (2)C21—C26—H32119.6
 

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