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A modification of a B—Cl 1,2–aza­borinine precursor with anthracenyl lithium generates an air-stable analog of cyclo­hexa­diene. In the crystal packing, van der Waals inter­actions are dominant.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023008381/vm2290sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023008381/vm2290Isup3.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2056989023008381/vm2290sup4.pdf
Experimental Data, NMR Spectra, Platon Output, Output from Computational Geometry Optimization.

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023008381/vm2290Isup4.cml
Supplementary material

CCDC reference: 2297014

Computing details top

Data collection: PHOTON (Bruker, 2019); cell refinement: SAINT V8.40A (Bruker, 2019); data reduction: SAINT V8.40A (Bruker, 2019); program(s) used to solve structure: SHELXT2014/5 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL Sheldrick, 2015b); molecular graphics: Olex2 1.5 (Dolomanov et al., 2009) ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009), publCIF (Westrip, (2010).

2-(Anthracen-9-yl)-1-(tert-butyldimethylsilyl)-3,6-dihydro-1λ4,2λ4-azaborinine top
Crystal data top
C24H30BNSiDx = 1.162 Mg m3
Mr = 371.39Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 9845 reflections
a = 13.3292 (6) Åθ = 2.5–30.5°
b = 11.1365 (5) ŵ = 0.12 mm1
c = 28.5973 (12) ÅT = 100 K
V = 4245.0 (3) Å3Block, colourless
Z = 80.28 × 0.22 × 0.2 mm
F(000) = 1600
Data collection top
Bruker Photon 100
diffractometer
5264 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs4416 reflections with I > 2σ(I)
Mirror optics monochromatorRint = 0.049
Detector resolution: 7.9 pixels mm-1θmax = 28.3°, θmin = 2.5°
ω and φ scansh = 1717
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1414
Tmin = 0.707, Tmax = 0.746l = 3838
67479 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0421P)2 + 2.6379P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.001
5264 reflectionsΔρmax = 0.37 e Å3
249 parametersΔρmin = 0.28 e Å3
0 restraints
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Si10.64414 (3)0.53526 (3)0.67676 (2)0.01305 (9)
N10.59622 (8)0.46229 (9)0.62665 (4)0.0121 (2)
C110.52126 (9)0.64751 (11)0.58088 (4)0.0119 (2)
C190.41726 (10)0.83144 (12)0.58633 (5)0.0149 (3)
C120.59392 (9)0.71475 (11)0.55610 (4)0.0126 (2)
C240.43227 (9)0.70565 (11)0.59506 (4)0.0130 (2)
C170.57825 (10)0.84029 (12)0.54660 (5)0.0146 (3)
C180.49112 (10)0.89607 (12)0.56257 (5)0.0168 (3)
H180.4818500.9795110.5571980.020*
C130.68530 (10)0.66195 (12)0.53987 (4)0.0153 (3)
H130.6984760.5799030.5465720.018*
C160.65239 (10)0.90463 (12)0.52065 (5)0.0180 (3)
H160.6424150.9875000.5142920.022*
C230.35484 (10)0.64256 (12)0.61956 (5)0.0166 (3)
H230.3633080.5595480.6261160.020*
C140.75406 (10)0.72648 (12)0.51500 (5)0.0182 (3)
H140.8138070.6888160.5043720.022*
C20.48012 (10)0.29143 (12)0.57271 (5)0.0184 (3)
H20.4299130.2391090.5608360.022*
C10.48884 (10)0.41613 (12)0.55382 (5)0.0164 (3)
H1A0.4211310.4454680.5453450.020*
H1B0.5297190.4141800.5249230.020*
C30.54188 (11)0.25311 (12)0.60593 (5)0.0186 (3)
H30.5344850.1738180.6176850.022*
C150.73675 (11)0.84979 (13)0.50489 (5)0.0195 (3)
H150.7843450.8938320.4870810.023*
C200.32658 (11)0.88722 (13)0.60194 (5)0.0200 (3)
H200.3162060.9703320.5962360.024*
C70.58707 (11)0.46528 (13)0.73184 (5)0.0208 (3)
C50.61517 (11)0.69869 (12)0.67683 (5)0.0194 (3)
H5A0.6399790.7350620.6478490.029*
H5B0.6478560.7368980.7036850.029*
H5C0.5424320.7102050.6790060.029*
C40.62300 (10)0.33186 (11)0.62535 (5)0.0155 (3)
H4A0.6389450.3049620.6574940.019*
H4B0.6842080.3216570.6061450.019*
C220.26936 (10)0.69877 (14)0.63369 (5)0.0207 (3)
H220.2188940.6545250.6496130.025*
C210.25508 (11)0.82314 (14)0.62480 (5)0.0221 (3)
H210.1952740.8616390.6348920.027*
C60.78352 (10)0.52013 (13)0.67616 (6)0.0236 (3)
H6A0.8016670.4348600.6759460.035*
H6B0.8115890.5584990.7040890.035*
H6C0.8105250.5591000.6481300.035*
C80.47669 (12)0.43301 (16)0.72304 (6)0.0311 (4)
H8A0.4404950.5044370.7122720.047*
H8B0.4464150.4038170.7521300.047*
H8C0.4727080.3701870.6991210.047*
B10.53820 (10)0.50755 (13)0.58960 (5)0.0119 (3)
C90.64271 (14)0.35359 (15)0.74992 (6)0.0345 (4)
H9A0.6356040.2880800.7272760.052*
H9B0.6140210.3289390.7799750.052*
H9C0.7139600.3725540.7540270.052*
C100.59141 (18)0.55923 (17)0.77124 (6)0.0448 (5)
H10A0.6609670.5852540.7757640.067*
H10B0.5660820.5237100.8002850.067*
H10C0.5499360.6285530.7627620.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Si10.01541 (18)0.01078 (17)0.01295 (17)0.00045 (13)0.00323 (13)0.00092 (13)
N10.0150 (5)0.0087 (5)0.0127 (5)0.0004 (4)0.0005 (4)0.0003 (4)
C110.0138 (6)0.0115 (6)0.0105 (6)0.0009 (5)0.0033 (4)0.0001 (5)
C190.0156 (6)0.0136 (6)0.0154 (6)0.0021 (5)0.0050 (5)0.0010 (5)
C120.0149 (6)0.0115 (6)0.0114 (6)0.0008 (5)0.0037 (5)0.0004 (5)
C240.0136 (6)0.0130 (6)0.0126 (6)0.0001 (5)0.0036 (5)0.0005 (5)
C170.0173 (6)0.0122 (6)0.0144 (6)0.0028 (5)0.0054 (5)0.0009 (5)
C180.0204 (7)0.0112 (6)0.0187 (7)0.0011 (5)0.0055 (5)0.0009 (5)
C130.0177 (6)0.0132 (6)0.0150 (6)0.0005 (5)0.0005 (5)0.0012 (5)
C160.0212 (7)0.0133 (6)0.0193 (7)0.0048 (5)0.0053 (5)0.0046 (5)
C230.0177 (6)0.0159 (6)0.0162 (6)0.0014 (5)0.0013 (5)0.0008 (5)
C140.0180 (6)0.0195 (7)0.0171 (6)0.0019 (5)0.0020 (5)0.0027 (5)
C20.0200 (7)0.0127 (6)0.0224 (7)0.0042 (5)0.0023 (5)0.0027 (5)
C10.0204 (7)0.0136 (6)0.0152 (6)0.0005 (5)0.0034 (5)0.0009 (5)
C30.0249 (7)0.0088 (6)0.0221 (7)0.0019 (5)0.0014 (5)0.0007 (5)
C150.0210 (7)0.0210 (7)0.0164 (6)0.0092 (6)0.0001 (5)0.0030 (5)
C200.0209 (7)0.0173 (7)0.0219 (7)0.0061 (5)0.0035 (5)0.0020 (5)
C70.0302 (8)0.0196 (7)0.0125 (6)0.0011 (6)0.0000 (5)0.0005 (5)
C50.0262 (7)0.0131 (6)0.0190 (7)0.0001 (5)0.0063 (6)0.0036 (5)
C40.0204 (7)0.0097 (6)0.0164 (6)0.0031 (5)0.0047 (5)0.0009 (5)
C220.0160 (7)0.0259 (7)0.0202 (7)0.0021 (6)0.0014 (5)0.0003 (6)
C210.0168 (7)0.0256 (7)0.0238 (7)0.0059 (6)0.0002 (6)0.0042 (6)
C60.0174 (7)0.0185 (7)0.0349 (8)0.0013 (5)0.0076 (6)0.0005 (6)
C80.0264 (8)0.0412 (10)0.0256 (8)0.0016 (7)0.0092 (6)0.0085 (7)
B10.0116 (6)0.0116 (6)0.0124 (6)0.0003 (5)0.0016 (5)0.0005 (5)
C90.0447 (10)0.0350 (9)0.0238 (8)0.0081 (8)0.0028 (7)0.0144 (7)
C100.0817 (15)0.0363 (10)0.0165 (8)0.0084 (10)0.0059 (9)0.0064 (7)
Geometric parameters (Å, º) top
Si1—N11.7669 (11)C1—H1B0.9900
Si1—C71.9148 (14)C1—B11.5863 (19)
Si1—C51.8606 (14)C3—H30.9500
Si1—C61.8655 (15)C3—C41.4988 (18)
N1—C41.4963 (16)C15—H150.9500
N1—B11.4052 (17)C20—H200.9500
C11—C121.4144 (17)C20—C211.358 (2)
C11—C241.4108 (18)C7—C81.535 (2)
C11—B11.5946 (18)C7—C91.538 (2)
C19—C241.4370 (18)C7—C101.539 (2)
C19—C181.3960 (19)C5—H5A0.9800
C19—C201.4304 (19)C5—H5B0.9800
C12—C171.4395 (18)C5—H5C0.9800
C12—C131.4300 (18)C4—H4A0.9900
C24—C231.4318 (18)C4—H4B0.9900
C17—C181.3940 (19)C22—H220.9500
C17—C161.4286 (19)C22—C211.421 (2)
C18—H180.9500C21—H210.9500
C13—H130.9500C6—H6A0.9800
C13—C141.3646 (19)C6—H6B0.9800
C16—H160.9500C6—H6C0.9800
C16—C151.357 (2)C8—H8A0.9800
C23—H230.9500C8—H8B0.9800
C23—C221.3613 (19)C8—H8C0.9800
C14—H140.9500C9—H9A0.9800
C14—C151.422 (2)C9—H9B0.9800
C2—H20.9500C9—H9C0.9800
C2—C11.4947 (18)C10—H10A0.9800
C2—C31.3276 (19)C10—H10B0.9800
C1—H1A0.9900C10—H10C0.9800
N1—Si1—C7109.65 (6)C19—C20—H20119.5
N1—Si1—C5112.07 (6)C21—C20—C19121.00 (13)
N1—Si1—C6108.12 (6)C21—C20—H20119.5
C5—Si1—C7108.35 (7)C8—C7—Si1109.95 (10)
C5—Si1—C6107.16 (7)C8—C7—C9109.14 (13)
C6—Si1—C7111.50 (7)C8—C7—C10108.36 (14)
C4—N1—Si1112.36 (8)C9—C7—Si1114.47 (11)
B1—N1—Si1130.21 (9)C9—C7—C10106.60 (14)
B1—N1—C4117.43 (10)C10—C7—Si1108.10 (11)
C12—C11—B1119.92 (11)Si1—C5—H5A109.5
C24—C11—C12118.47 (11)Si1—C5—H5B109.5
C24—C11—B1121.51 (11)Si1—C5—H5C109.5
C18—C19—C24119.27 (12)H5A—C5—H5B109.5
C18—C19—C20121.60 (12)H5A—C5—H5C109.5
C20—C19—C24119.13 (12)H5B—C5—H5C109.5
C11—C12—C17120.62 (12)N1—C4—C3113.90 (11)
C11—C12—C13121.88 (11)N1—C4—H4A108.8
C13—C12—C17117.49 (12)N1—C4—H4B108.8
C11—C24—C19120.97 (12)C3—C4—H4A108.8
C11—C24—C23121.44 (12)C3—C4—H4B108.8
C23—C24—C19117.58 (12)H4A—C4—H4B107.7
C18—C17—C12119.46 (12)C23—C22—H22119.8
C18—C17—C16121.54 (12)C23—C22—C21120.48 (13)
C16—C17—C12119.00 (12)C21—C22—H22119.8
C19—C18—H18119.4C20—C21—C22120.28 (13)
C17—C18—C19121.15 (12)C20—C21—H21119.9
C17—C18—H18119.4C22—C21—H21119.9
C12—C13—H13119.2Si1—C6—H6A109.5
C14—C13—C12121.65 (12)Si1—C6—H6B109.5
C14—C13—H13119.2Si1—C6—H6C109.5
C17—C16—H16119.3H6A—C6—H6B109.5
C15—C16—C17121.34 (12)H6A—C6—H6C109.5
C15—C16—H16119.3H6B—C6—H6C109.5
C24—C23—H23119.2C7—C8—H8A109.5
C22—C23—C24121.53 (13)C7—C8—H8B109.5
C22—C23—H23119.2C7—C8—H8C109.5
C13—C14—H14119.8H8A—C8—H8B109.5
C13—C14—C15120.36 (13)H8A—C8—H8C109.5
C15—C14—H14119.8H8B—C8—H8C109.5
C1—C2—H2119.7N1—B1—C11123.12 (11)
C3—C2—H2119.7N1—B1—C1118.97 (11)
C3—C2—C1120.60 (12)C1—B1—C11117.89 (11)
C2—C1—H1A108.9C7—C9—H9A109.5
C2—C1—H1B108.9C7—C9—H9B109.5
C2—C1—B1113.30 (11)C7—C9—H9C109.5
H1A—C1—H1B107.7H9A—C9—H9B109.5
B1—C1—H1A108.9H9A—C9—H9C109.5
B1—C1—H1B108.9H9B—C9—H9C109.5
C2—C3—H3119.2C7—C10—H10A109.5
C2—C3—C4121.63 (12)C7—C10—H10B109.5
C4—C3—H3119.2C7—C10—H10C109.5
C16—C15—C14120.11 (13)H10A—C10—H10B109.5
C16—C15—H15119.9H10A—C10—H10C109.5
C14—C15—H15119.9H10B—C10—H10C109.5
Si1—N1—C4—C3143.11 (10)C18—C17—C16—C15179.54 (13)
Si1—N1—B1—C1112.58 (19)C13—C12—C17—C18178.75 (12)
Si1—N1—B1—C1168.86 (9)C13—C12—C17—C161.69 (18)
C11—C12—C17—C180.84 (18)C13—C14—C15—C161.1 (2)
C11—C12—C17—C16178.72 (12)C16—C17—C18—C19177.47 (12)
C11—C12—C13—C14178.38 (12)C23—C22—C21—C200.2 (2)
C11—C24—C23—C22179.33 (13)C2—C1—B1—N120.11 (17)
C19—C24—C23—C220.77 (19)C2—C1—B1—C11161.25 (12)
C19—C20—C21—C220.1 (2)C2—C3—C4—N132.76 (19)
C12—C11—C24—C192.54 (18)C1—C2—C3—C40.7 (2)
C12—C11—C24—C23178.94 (12)C3—C2—C1—B125.46 (19)
C12—C11—B1—N183.53 (16)C20—C19—C24—C11179.05 (12)
C12—C11—B1—C195.05 (14)C20—C19—C24—C230.48 (18)
C12—C17—C18—C192.07 (19)C20—C19—C18—C17178.58 (13)
C12—C17—C16—C150.0 (2)C7—Si1—N1—C462.08 (10)
C12—C13—C14—C150.7 (2)C7—Si1—N1—B1117.35 (12)
C24—C11—C12—C171.44 (18)C5—Si1—N1—C4177.55 (9)
C24—C11—C12—C13178.99 (11)C5—Si1—N1—B13.01 (14)
C24—C11—B1—N1100.06 (15)C4—N1—B1—C11168.01 (11)
C24—C11—B1—C181.36 (15)C4—N1—B1—C110.55 (17)
C24—C19—C18—C170.99 (19)C6—Si1—N1—C459.67 (10)
C24—C19—C20—C210.1 (2)C6—Si1—N1—B1120.89 (12)
C24—C23—C22—C210.6 (2)B1—N1—C4—C336.40 (16)
C17—C12—C13—C142.04 (19)B1—C11—C12—C17177.96 (11)
C17—C16—C15—C141.4 (2)B1—C11—C12—C132.47 (18)
C18—C19—C24—C111.37 (19)B1—C11—C24—C19179.00 (11)
C18—C19—C24—C23179.94 (12)B1—C11—C24—C232.49 (18)
C18—C19—C20—C21179.65 (13)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg5, Cg7 and Cg3 are the centroids of rings C11–C12/C17–C19/C24, C11–C18, C11–C24 and C12–C17, respectively.
D—H···AD—HH···AD···AD—H···A
C5—H5A···Cg20.982.863.4529 (15)120
C5—H5A···Cg50.982.913.7305 (15)142
C5—H5A···Cg70.982.883.4772 (15)120
C2—H2···Cg3i0.952.923.6380 (15)133
C4—H4B···Cg3ii0.992.973.9373 (15)167
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+3/2, y1/2, z.
Interatomic contacts with the title molecule I as percentage contributions to the Hirshfeld surface. top
EntryContactPercentage contribution
1all···all100
2H···H77
3C···C0.1
4C···H/H···C22.8
5B···all/all···B0
6N···all/all···N0
7Si···all/all···Si0
 

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