Synthesis and crystal structure of 2-(anthracen-9-yl)-1-(tert-butyl­dimethyl­sil­yl)-3,6-di­hydro-1λ⁴,2λ⁴-aza­borinine

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.042
• wR factor = 0.103
• Data-to-parameter ratio = 21.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C NonSolvent   Resd 1  C   Ueq(max)/Ueq(min) Range        3.8 Ratio
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      3.027 Check

Alert level G
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          2 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          2 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          1 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         18 Info

   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
   4 ALERT level G = General information/check it is not something unexpected

   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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

Crystal data

C24H30BNSi	Dx = 1.162 Mg m^−3
Mr = 371.39	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 9845 reflections
a = 13.3292 (6) Å	θ = 2.5–30.5°
b = 11.1365 (5) Å	µ = 0.12 mm^−1
c = 28.5973 (12) Å	T = 100 K
V = 4245.0 (3) Å^3	Block, colourless
Z = 8	0.28 × 0.22 × 0.2 mm
F(000) = 1600

Data collection

Bruker Photon 100 diffractometer	5264 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	4416 reflections with I > 2σ(I)
Mirror optics monochromator	Rint = 0.049
Detector resolution: 7.9 pixels mm^-1	θmax = 28.3°, θmin = 2.5°
ω and φ scans	h = −17→17
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −14→14
Tmin = 0.707, Tmax = 0.746	l = −38→38
67479 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0421P)^2 + 2.6379P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.001
5264 reflections	Δρmax = 0.37 e Å^−3
249 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Si1	0.64414 (3)	0.53526 (3)	0.67676 (2)	0.01305 (9)
N1	0.59622 (8)	0.46229 (9)	0.62665 (4)	0.0121 (2)
C11	0.52126 (9)	0.64751 (11)	0.58088 (4)	0.0119 (2)
C19	0.41726 (10)	0.83144 (12)	0.58633 (5)	0.0149 (3)
C12	0.59392 (9)	0.71475 (11)	0.55610 (4)	0.0126 (2)
C24	0.43227 (9)	0.70565 (11)	0.59506 (4)	0.0130 (2)
C17	0.57825 (10)	0.84029 (12)	0.54660 (5)	0.0146 (3)
C18	0.49112 (10)	0.89607 (12)	0.56257 (5)	0.0168 (3)
H18	0.481850	0.979511	0.557198	0.020*
C13	0.68530 (10)	0.66195 (12)	0.53987 (4)	0.0153 (3)
H13	0.698476	0.579903	0.546572	0.018*
C16	0.65239 (10)	0.90463 (12)	0.52065 (5)	0.0180 (3)
H16	0.642415	0.987500	0.514292	0.022*
C23	0.35484 (10)	0.64256 (12)	0.61956 (5)	0.0166 (3)
H23	0.363308	0.559548	0.626116	0.020*
C14	0.75406 (10)	0.72648 (12)	0.51500 (5)	0.0182 (3)
H14	0.813807	0.688816	0.504372	0.022*
C2	0.48012 (10)	0.29143 (12)	0.57271 (5)	0.0184 (3)
H2	0.429913	0.239109	0.560836	0.022*
C1	0.48884 (10)	0.41613 (12)	0.55382 (5)	0.0164 (3)
H1A	0.421131	0.445468	0.545345	0.020*
H1B	0.529719	0.414180	0.524923	0.020*
C3	0.54188 (11)	0.25311 (12)	0.60593 (5)	0.0186 (3)
H3	0.534485	0.173818	0.617685	0.022*
C15	0.73675 (11)	0.84979 (13)	0.50489 (5)	0.0195 (3)
H15	0.784345	0.893832	0.487081	0.023*
C20	0.32658 (11)	0.88722 (13)	0.60194 (5)	0.0200 (3)
H20	0.316206	0.970332	0.596236	0.024*
C7	0.58707 (11)	0.46528 (13)	0.73184 (5)	0.0208 (3)
C5	0.61517 (11)	0.69869 (12)	0.67683 (5)	0.0194 (3)
H5A	0.639979	0.735062	0.647849	0.029*
H5B	0.647856	0.736898	0.703685	0.029*
H5C	0.542432	0.710205	0.679006	0.029*
C4	0.62300 (10)	0.33186 (11)	0.62535 (5)	0.0155 (3)
H4A	0.638945	0.304962	0.657494	0.019*
H4B	0.684208	0.321657	0.606145	0.019*
C22	0.26936 (10)	0.69877 (14)	0.63369 (5)	0.0207 (3)
H22	0.218894	0.654525	0.649613	0.025*
C21	0.25508 (11)	0.82314 (14)	0.62480 (5)	0.0221 (3)
H21	0.195274	0.861639	0.634892	0.027*
C6	0.78352 (10)	0.52013 (13)	0.67616 (6)	0.0236 (3)
H6A	0.801667	0.434860	0.675946	0.035*
H6B	0.811589	0.558499	0.704089	0.035*
H6C	0.810525	0.559100	0.648130	0.035*
C8	0.47669 (12)	0.43301 (16)	0.72304 (6)	0.0311 (4)
H8A	0.440495	0.504437	0.712272	0.047*
H8B	0.446415	0.403817	0.752130	0.047*
H8C	0.472708	0.370187	0.699121	0.047*
B1	0.53820 (10)	0.50755 (13)	0.58960 (5)	0.0119 (3)
C9	0.64271 (14)	0.35359 (15)	0.74992 (6)	0.0345 (4)
H9A	0.635604	0.288080	0.727276	0.052*
H9B	0.614021	0.328939	0.779975	0.052*
H9C	0.713960	0.372554	0.754027	0.052*
C10	0.59141 (18)	0.55923 (17)	0.77124 (6)	0.0448 (5)
H10A	0.660967	0.585254	0.775764	0.067*
H10B	0.566082	0.523710	0.800285	0.067*
H10C	0.549936	0.628553	0.762762	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.01541 (18)	0.01078 (17)	0.01295 (17)	−0.00045 (13)	−0.00323 (13)	−0.00092 (13)
N1	0.0150 (5)	0.0087 (5)	0.0127 (5)	0.0004 (4)	−0.0005 (4)	−0.0003 (4)
C11	0.0138 (6)	0.0115 (6)	0.0105 (6)	−0.0009 (5)	−0.0033 (4)	−0.0001 (5)
C19	0.0156 (6)	0.0136 (6)	0.0154 (6)	0.0021 (5)	−0.0050 (5)	−0.0010 (5)
C12	0.0149 (6)	0.0115 (6)	0.0114 (6)	−0.0008 (5)	−0.0037 (5)	0.0004 (5)
C24	0.0136 (6)	0.0130 (6)	0.0126 (6)	0.0001 (5)	−0.0036 (5)	−0.0005 (5)
C17	0.0173 (6)	0.0122 (6)	0.0144 (6)	−0.0028 (5)	−0.0054 (5)	0.0009 (5)
C18	0.0204 (7)	0.0112 (6)	0.0187 (7)	0.0011 (5)	−0.0055 (5)	0.0009 (5)
C13	0.0177 (6)	0.0132 (6)	0.0150 (6)	−0.0005 (5)	−0.0005 (5)	−0.0012 (5)
C16	0.0212 (7)	0.0133 (6)	0.0193 (7)	−0.0048 (5)	−0.0053 (5)	0.0046 (5)
C23	0.0177 (6)	0.0159 (6)	0.0162 (6)	−0.0014 (5)	−0.0013 (5)	0.0008 (5)
C14	0.0180 (6)	0.0195 (7)	0.0171 (6)	−0.0019 (5)	0.0020 (5)	−0.0027 (5)
C2	0.0200 (7)	0.0127 (6)	0.0224 (7)	−0.0042 (5)	−0.0023 (5)	−0.0027 (5)
C1	0.0204 (7)	0.0136 (6)	0.0152 (6)	−0.0005 (5)	−0.0034 (5)	0.0009 (5)
C3	0.0249 (7)	0.0088 (6)	0.0221 (7)	−0.0019 (5)	−0.0014 (5)	0.0007 (5)
C15	0.0210 (7)	0.0210 (7)	0.0164 (6)	−0.0092 (6)	0.0001 (5)	0.0030 (5)
C20	0.0209 (7)	0.0173 (7)	0.0219 (7)	0.0061 (5)	−0.0035 (5)	−0.0020 (5)
C7	0.0302 (8)	0.0196 (7)	0.0125 (6)	0.0011 (6)	0.0000 (5)	0.0005 (5)
C5	0.0262 (7)	0.0131 (6)	0.0190 (7)	−0.0001 (5)	−0.0063 (6)	−0.0036 (5)
C4	0.0204 (7)	0.0097 (6)	0.0164 (6)	0.0031 (5)	−0.0047 (5)	−0.0009 (5)
C22	0.0160 (7)	0.0259 (7)	0.0202 (7)	−0.0021 (6)	0.0014 (5)	−0.0003 (6)
C21	0.0168 (7)	0.0256 (7)	0.0238 (7)	0.0059 (6)	0.0002 (6)	−0.0042 (6)
C6	0.0174 (7)	0.0185 (7)	0.0349 (8)	−0.0013 (5)	−0.0076 (6)	0.0005 (6)
C8	0.0264 (8)	0.0412 (10)	0.0256 (8)	−0.0016 (7)	0.0092 (6)	0.0085 (7)
B1	0.0116 (6)	0.0116 (6)	0.0124 (6)	−0.0003 (5)	0.0016 (5)	0.0005 (5)
C9	0.0447 (10)	0.0350 (9)	0.0238 (8)	0.0081 (8)	0.0028 (7)	0.0144 (7)
C10	0.0817 (15)	0.0363 (10)	0.0165 (8)	−0.0084 (10)	0.0059 (9)	−0.0064 (7)

Geometric parameters (Å, º)

Si1—N1	1.7669 (11)	C1—H1B	0.9900
Si1—C7	1.9148 (14)	C1—B1	1.5863 (19)
Si1—C5	1.8606 (14)	C3—H3	0.9500
Si1—C6	1.8655 (15)	C3—C4	1.4988 (18)
N1—C4	1.4963 (16)	C15—H15	0.9500
N1—B1	1.4052 (17)	C20—H20	0.9500
C11—C12	1.4144 (17)	C20—C21	1.358 (2)
C11—C24	1.4108 (18)	C7—C8	1.535 (2)
C11—B1	1.5946 (18)	C7—C9	1.538 (2)
C19—C24	1.4370 (18)	C7—C10	1.539 (2)
C19—C18	1.3960 (19)	C5—H5A	0.9800
C19—C20	1.4304 (19)	C5—H5B	0.9800
C12—C17	1.4395 (18)	C5—H5C	0.9800
C12—C13	1.4300 (18)	C4—H4A	0.9900
C24—C23	1.4318 (18)	C4—H4B	0.9900
C17—C18	1.3940 (19)	C22—H22	0.9500
C17—C16	1.4286 (19)	C22—C21	1.421 (2)
C18—H18	0.9500	C21—H21	0.9500
C13—H13	0.9500	C6—H6A	0.9800
C13—C14	1.3646 (19)	C6—H6B	0.9800
C16—H16	0.9500	C6—H6C	0.9800
C16—C15	1.357 (2)	C8—H8A	0.9800
C23—H23	0.9500	C8—H8B	0.9800
C23—C22	1.3613 (19)	C8—H8C	0.9800
C14—H14	0.9500	C9—H9A	0.9800
C14—C15	1.422 (2)	C9—H9B	0.9800
C2—H2	0.9500	C9—H9C	0.9800
C2—C1	1.4947 (18)	C10—H10A	0.9800
C2—C3	1.3276 (19)	C10—H10B	0.9800
C1—H1A	0.9900	C10—H10C	0.9800
N1—Si1—C7	109.65 (6)	C19—C20—H20	119.5
N1—Si1—C5	112.07 (6)	C21—C20—C19	121.00 (13)
N1—Si1—C6	108.12 (6)	C21—C20—H20	119.5
C5—Si1—C7	108.35 (7)	C8—C7—Si1	109.95 (10)
C5—Si1—C6	107.16 (7)	C8—C7—C9	109.14 (13)
C6—Si1—C7	111.50 (7)	C8—C7—C10	108.36 (14)
C4—N1—Si1	112.36 (8)	C9—C7—Si1	114.47 (11)
B1—N1—Si1	130.21 (9)	C9—C7—C10	106.60 (14)
B1—N1—C4	117.43 (10)	C10—C7—Si1	108.10 (11)
C12—C11—B1	119.92 (11)	Si1—C5—H5A	109.5
C24—C11—C12	118.47 (11)	Si1—C5—H5B	109.5
C24—C11—B1	121.51 (11)	Si1—C5—H5C	109.5
C18—C19—C24	119.27 (12)	H5A—C5—H5B	109.5
C18—C19—C20	121.60 (12)	H5A—C5—H5C	109.5
C20—C19—C24	119.13 (12)	H5B—C5—H5C	109.5
C11—C12—C17	120.62 (12)	N1—C4—C3	113.90 (11)
C11—C12—C13	121.88 (11)	N1—C4—H4A	108.8
C13—C12—C17	117.49 (12)	N1—C4—H4B	108.8
C11—C24—C19	120.97 (12)	C3—C4—H4A	108.8
C11—C24—C23	121.44 (12)	C3—C4—H4B	108.8
C23—C24—C19	117.58 (12)	H4A—C4—H4B	107.7
C18—C17—C12	119.46 (12)	C23—C22—H22	119.8
C18—C17—C16	121.54 (12)	C23—C22—C21	120.48 (13)
C16—C17—C12	119.00 (12)	C21—C22—H22	119.8
C19—C18—H18	119.4	C20—C21—C22	120.28 (13)
C17—C18—C19	121.15 (12)	C20—C21—H21	119.9
C17—C18—H18	119.4	C22—C21—H21	119.9
C12—C13—H13	119.2	Si1—C6—H6A	109.5
C14—C13—C12	121.65 (12)	Si1—C6—H6B	109.5
C14—C13—H13	119.2	Si1—C6—H6C	109.5
C17—C16—H16	119.3	H6A—C6—H6B	109.5
C15—C16—C17	121.34 (12)	H6A—C6—H6C	109.5
C15—C16—H16	119.3	H6B—C6—H6C	109.5
C24—C23—H23	119.2	C7—C8—H8A	109.5
C22—C23—C24	121.53 (13)	C7—C8—H8B	109.5
C22—C23—H23	119.2	C7—C8—H8C	109.5
C13—C14—H14	119.8	H8A—C8—H8B	109.5
C13—C14—C15	120.36 (13)	H8A—C8—H8C	109.5
C15—C14—H14	119.8	H8B—C8—H8C	109.5
C1—C2—H2	119.7	N1—B1—C11	123.12 (11)
C3—C2—H2	119.7	N1—B1—C1	118.97 (11)
C3—C2—C1	120.60 (12)	C1—B1—C11	117.89 (11)
C2—C1—H1A	108.9	C7—C9—H9A	109.5
C2—C1—H1B	108.9	C7—C9—H9B	109.5
C2—C1—B1	113.30 (11)	C7—C9—H9C	109.5
H1A—C1—H1B	107.7	H9A—C9—H9B	109.5
B1—C1—H1A	108.9	H9A—C9—H9C	109.5
B1—C1—H1B	108.9	H9B—C9—H9C	109.5
C2—C3—H3	119.2	C7—C10—H10A	109.5
C2—C3—C4	121.63 (12)	C7—C10—H10B	109.5
C4—C3—H3	119.2	C7—C10—H10C	109.5
C16—C15—C14	120.11 (13)	H10A—C10—H10B	109.5
C16—C15—H15	119.9	H10A—C10—H10C	109.5
C14—C15—H15	119.9	H10B—C10—H10C	109.5
Si1—N1—C4—C3	143.11 (10)	C18—C17—C16—C15	−179.54 (13)
Si1—N1—B1—C11	12.58 (19)	C13—C12—C17—C18	−178.75 (12)
Si1—N1—B1—C1	−168.86 (9)	C13—C12—C17—C16	1.69 (18)
C11—C12—C17—C18	0.84 (18)	C13—C14—C15—C16	1.1 (2)
C11—C12—C17—C16	−178.72 (12)	C16—C17—C18—C19	177.47 (12)
C11—C12—C13—C14	178.38 (12)	C23—C22—C21—C20	0.2 (2)
C11—C24—C23—C22	179.33 (13)	C2—C1—B1—N1	20.11 (17)
C19—C24—C23—C22	0.77 (19)	C2—C1—B1—C11	−161.25 (12)
C19—C20—C21—C22	0.1 (2)	C2—C3—C4—N1	32.76 (19)
C12—C11—C24—C19	−2.54 (18)	C1—C2—C3—C4	−0.7 (2)
C12—C11—C24—C23	178.94 (12)	C3—C2—C1—B1	−25.46 (19)
C12—C11—B1—N1	83.53 (16)	C20—C19—C24—C11	−179.05 (12)
C12—C11—B1—C1	−95.05 (14)	C20—C19—C24—C23	−0.48 (18)
C12—C17—C18—C19	−2.07 (19)	C20—C19—C18—C17	−178.58 (13)
C12—C17—C16—C15	0.0 (2)	C7—Si1—N1—C4	−62.08 (10)
C12—C13—C14—C15	0.7 (2)	C7—Si1—N1—B1	117.35 (12)
C24—C11—C12—C17	1.44 (18)	C5—Si1—N1—C4	177.55 (9)
C24—C11—C12—C13	−178.99 (11)	C5—Si1—N1—B1	−3.01 (14)
C24—C11—B1—N1	−100.06 (15)	C4—N1—B1—C11	−168.01 (11)
C24—C11—B1—C1	81.36 (15)	C4—N1—B1—C1	10.55 (17)
C24—C19—C18—C17	0.99 (19)	C6—Si1—N1—C4	59.67 (10)
C24—C19—C20—C21	0.1 (2)	C6—Si1—N1—B1	−120.89 (12)
C24—C23—C22—C21	−0.6 (2)	B1—N1—C4—C3	−36.40 (16)
C17—C12—C13—C14	−2.04 (19)	B1—C11—C12—C17	177.96 (11)
C17—C16—C15—C14	−1.4 (2)	B1—C11—C12—C13	−2.47 (18)
C18—C19—C24—C11	1.37 (19)	B1—C11—C24—C19	−179.00 (11)
C18—C19—C24—C23	179.94 (12)	B1—C11—C24—C23	2.49 (18)
C18—C19—C20—C21	179.65 (13)

Hydrogen-bond geometry (Å, º)

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···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg2	0.98	2.86	3.4529 (15)	120
C5—H5A···Cg5	0.98	2.91	3.7305 (15)	142
C5—H5A···Cg7	0.98	2.88	3.4772 (15)	120
C2—H2···Cg3^i	0.95	2.92	3.6380 (15)	133
C4—H4B···Cg3^ii	0.99	2.97	3.9373 (15)	167

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+3/2, y−1/2, z.