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In the title compound, C13H14BN3O, the aziridine ring is an almost equilateral triangle, the C—C distance being slightly shorter than the C—N distances, probably because of the dative B—N bond. The five-membered ring, composed of two C atoms and N, B and O atoms, is fused with the aziridine ring to form a six-membered ring with a chair conformation.
Supporting information
CCDC reference: 229091
The title compound was prepared from the reaction of 1-[(S)-1-phenylethyl]-2 −t-butyldimethylsilyloxymethylaziridine with three molar equivalents of cyanotrimethylsilane and one equivalent of boron trifluroride diethyl etherate at 233 K in CH2Cl2. The initial product (85% yield), a white solid, was recrystallized from dichloromethane to afford single crystals suitable for X-ray diffraction studies. Analysis found: C 65.2, H 5.77, N 17.5%; calculated: C 65.3, H 5.90, N 17.6
The absolute configuration cannot be determined in the absence of significant anomalous scattering and was therefore assigned by reference to the starting materials. Friedel opposite reflections were merged. The positions of the H atoms were generated geometically and refined as riding (SHELXL97; Sheldrick, 1997).
Data collection: MXC3 (MacScience, 1994); cell refinement: MXC3; data reduction: MXC3; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Dicyano{[(1
S)-(1-phenylethyl)aziridin-2-yl]methanolato-
κ2N,
O}boron
top
Crystal data top
C13H14BN3O | Z = 1 |
Mr = 239.08 | F(000) = 126 |
Triclinic, P1 | Dx = 1.216 Mg m−3 |
a = 6.710 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 6.767 (4) Å | Cell parameters from 20 reflections |
c = 8.059 (5) Å | θ = 10–14° |
α = 71.51 (4)° | µ = 0.08 mm−1 |
β = 84.68 (5)° | T = 293 K |
γ = 70.16 (3)° | Rectangular, colourless |
V = 326.4 (3) Å3 | 0.5 × 0.4 × 0.3 mm |
Data collection top
MacScience MXC3 diffractometer | Rint = 0.020 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 2.7° |
Graphite monochromator | h = −8→8 |
ω–2θ scans | k = −8→8 |
1595 measured reflections | l = 0→10 |
1483 independent reflections | 2 standard reflections every 100 reflections |
1435 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0596P)2 + 0.0238P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
1483 reflections | Δρmax = 0.17 e Å−3 |
165 parameters | Δρmin = −0.15 e Å−3 |
3 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.09 (2) |
Crystal data top
C13H14BN3O | γ = 70.16 (3)° |
Mr = 239.08 | V = 326.4 (3) Å3 |
Triclinic, P1 | Z = 1 |
a = 6.710 (3) Å | Mo Kα radiation |
b = 6.767 (4) Å | µ = 0.08 mm−1 |
c = 8.059 (5) Å | T = 293 K |
α = 71.51 (4)° | 0.5 × 0.4 × 0.3 mm |
β = 84.68 (5)° | |
Data collection top
MacScience MXC3 diffractometer | Rint = 0.020 |
1595 measured reflections | 2 standard reflections every 100 reflections |
1483 independent reflections | intensity decay: none |
1435 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 3 restraints |
wR(F2) = 0.090 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.17 e Å−3 |
1483 reflections | Δρmin = −0.15 e Å−3 |
165 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C(1) | 0.3951 (3) | 0.1742 (3) | 0.9006 (2) | 0.0336 (4) | |
C(2) | 0.3368 (3) | 0.4116 (3) | 0.8755 (2) | 0.0305 (4) | |
C(3) | 0.2319 (3) | 0.4951 (3) | 1.0258 (3) | 0.0359 (4) | |
C(4) | 0.1521 (3) | 0.3504 (3) | 0.6268 (2) | 0.0282 (4) | |
C(5) | 0.1412 (4) | 0.1347 (4) | 0.6139 (3) | 0.0400 (5) | |
C(6) | 0.3154 (3) | 0.4337 (3) | 0.5104 (2) | 0.0301 (4) | |
C(7) | 0.5046 (3) | 0.2924 (4) | 0.4686 (3) | 0.0365 (4) | |
C(8) | 0.6532 (4) | 0.3785 (5) | 0.3663 (3) | 0.0515 (6) | |
C(9) | 0.6140 (5) | 0.6036 (5) | 0.3084 (3) | 0.0624 (8) | |
C(10) | 0.4286 (6) | 0.7424 (5) | 0.3490 (3) | 0.0667 (9) | |
C(11) | 0.2776 (4) | 0.6601 (4) | 0.4471 (3) | 0.0467 (6) | |
C(12) | −0.1921 (3) | 0.5691 (3) | 0.8498 (3) | 0.0327 (4) | |
C(13) | −0.0846 (3) | 0.1439 (3) | 1.0175 (3) | 0.0356 (4) | |
B | −0.0025 (3) | 0.3523 (3) | 0.9532 (3) | 0.0285 (4) | |
N(1) | 0.1875 (2) | 0.3229 (2) | 0.81644 (19) | 0.0243 (3) | |
N(2) | −0.3255 (3) | 0.7216 (3) | 0.7767 (3) | 0.0484 (5) | |
N(3) | −0.1448 (3) | −0.0010 (3) | 1.0667 (3) | 0.0525 (5) | |
O | 0.0872 (2) | 0.3772 (2) | 1.09578 (18) | 0.0359 (3) | |
H(1A) | 0.3944 | 0.0779 | 1.0189 | 0.040* | |
H(1B) | 0.5049 | 0.1113 | 0.8271 | 0.040* | |
H(2) | 0.4106 | 0.4982 | 0.7875 | 0.037* | |
H(3A) | 0.3362 | 0.4659 | 1.1138 | 0.043* | |
H(3B) | 0.1573 | 0.6526 | 0.9847 | 0.043* | |
H(4) | 0.0132 | 0.4626 | 0.5906 | 0.034* | |
H(5A) | 0.0234 | 0.1021 | 0.6798 | 0.060* | |
H(5B) | 0.2700 | 0.0177 | 0.6602 | 0.060* | |
H(5C) | 0.1232 | 0.1482 | 0.4935 | 0.060* | |
H(7) | 0.5320 | 0.1407 | 0.5089 | 0.044* | |
H(8) | 0.7786 | 0.2841 | 0.3372 | 0.062* | |
H(9) | 0.7140 | 0.6607 | 0.2417 | 0.075* | |
H(10) | 0.4034 | 0.8938 | 0.3104 | 0.080* | |
H(11) | 0.1502 | 0.7567 | 0.4709 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C(1) | 0.0231 (8) | 0.0399 (10) | 0.0281 (9) | −0.0014 (7) | −0.0036 (7) | −0.0059 (8) |
C(2) | 0.0257 (8) | 0.0423 (10) | 0.0258 (8) | −0.0163 (8) | −0.0005 (7) | −0.0077 (7) |
C(3) | 0.0380 (10) | 0.0446 (10) | 0.0313 (9) | −0.0185 (8) | 0.0020 (7) | −0.0149 (8) |
C(4) | 0.0251 (8) | 0.0322 (8) | 0.0245 (8) | −0.0053 (7) | −0.0019 (6) | −0.0086 (7) |
C(5) | 0.0408 (10) | 0.0459 (11) | 0.0429 (11) | −0.0203 (9) | 0.0024 (8) | −0.0204 (9) |
C(6) | 0.0373 (9) | 0.0312 (8) | 0.0202 (8) | −0.0111 (7) | −0.0004 (7) | −0.0055 (7) |
C(7) | 0.0345 (10) | 0.0436 (10) | 0.0261 (9) | −0.0092 (8) | 0.0013 (7) | −0.0074 (8) |
C(8) | 0.0374 (11) | 0.0894 (19) | 0.0291 (10) | −0.0248 (12) | 0.0053 (9) | −0.0169 (11) |
C(9) | 0.086 (2) | 0.097 (2) | 0.0272 (11) | −0.0652 (19) | 0.0153 (12) | −0.0160 (13) |
C(10) | 0.130 (3) | 0.0584 (16) | 0.0289 (11) | −0.0593 (19) | 0.0161 (14) | −0.0104 (11) |
C(11) | 0.0759 (16) | 0.0339 (10) | 0.0259 (10) | −0.0167 (10) | 0.0060 (10) | −0.0062 (8) |
C(12) | 0.0272 (9) | 0.0318 (9) | 0.0400 (10) | −0.0087 (8) | 0.0058 (8) | −0.0147 (8) |
C(13) | 0.0292 (9) | 0.0351 (10) | 0.0397 (10) | −0.0120 (8) | 0.0056 (7) | −0.0075 (8) |
B | 0.0232 (9) | 0.0293 (9) | 0.0310 (10) | −0.0073 (7) | 0.0055 (8) | −0.0094 (8) |
N(1) | 0.0206 (6) | 0.0251 (6) | 0.0251 (7) | −0.0063 (5) | 0.0000 (5) | −0.0063 (5) |
N(2) | 0.0383 (10) | 0.0378 (9) | 0.0615 (12) | 0.0002 (8) | −0.0029 (9) | −0.0177 (9) |
N(3) | 0.0464 (11) | 0.0452 (11) | 0.0633 (13) | −0.0230 (9) | 0.0067 (10) | −0.0061 (9) |
O | 0.0359 (7) | 0.0468 (8) | 0.0271 (6) | −0.0177 (6) | 0.0069 (5) | −0.0114 (6) |
Geometric parameters (Å, º) top
C(1)—C(2) | 1.468 (3) | C(6)—C(7) | 1.393 (3) |
C(1)—N(1) | 1.484 (2) | C(7)—C(8) | 1.396 (3) |
C(1)—H(1A) | 0.9700 | C(7)—H(7) | 0.9300 |
C(1)—H(1B) | 0.9700 | C(8)—C(9) | 1.381 (5) |
C(2)—N(1) | 1.506 (2) | C(8)—H(8) | 0.9300 |
C(2)—C(3) | 1.513 (3) | C(9)—C(10) | 1.365 (5) |
C(2)—H(2) | 0.9800 | C(9)—H(9) | 0.9300 |
C(3)—O | 1.427 (3) | C(10)—C(11) | 1.384 (4) |
C(3)—H(3A) | 0.9700 | C(10)—H(10) | 0.9300 |
C(3)—H(3B) | 0.9700 | C(11)—H(11) | 0.9300 |
C(4)—N(1) | 1.511 (2) | C(12)—N(2) | 1.140 (3) |
C(4)—C(6) | 1.514 (3) | C(12)—B | 1.618 (3) |
C(4)—C(5) | 1.523 (3) | C(13)—N(3) | 1.128 (3) |
C(4)—H(4) | 0.9800 | C(13)—B | 1.604 (3) |
C(5)—H(5A) | 0.9600 | B—O | 1.425 (3) |
C(5)—H(5B) | 0.9600 | B—N(1) | 1.608 (3) |
C(5)—H(5C) | 0.9600 | C(1)—N(3)i | 3.163 (4) |
C(6)—C(11) | 1.392 (3) | C(5)—N(1) | 2.463 (3) |
| | | |
C(2)—C(1)—N(1) | 61.34 (12) | C(7)—C(6)—C(4) | 122.60 (17) |
C(2)—C(1)—H(1A) | 117.6 | C(6)—C(7)—C(8) | 120.1 (2) |
N(1)—C(1)—H(1A) | 117.6 | C(6)—C(7)—H(7) | 120.0 |
C(2)—C(1)—H(1B) | 117.6 | C(8)—C(7)—H(7) | 120.0 |
N(1)—C(1)—H(1B) | 117.6 | C(9)—C(8)—C(7) | 120.0 (2) |
H(1A)—C(1)—H(1B) | 114.7 | C(9)—C(8)—H(8) | 120.0 |
C(1)—C(2)—N(1) | 59.85 (12) | C(7)—C(8)—H(8) | 120.0 |
C(1)—C(2)—C(3) | 117.62 (17) | C(10)—C(9)—C(8) | 120.0 (2) |
N(1)—C(2)—C(3) | 106.74 (15) | C(10)—C(9)—H(9) | 120.0 |
C(1)—C(2)—H(2) | 119.2 | C(8)—C(9)—H(9) | 120.0 |
N(1)—C(2)—H(2) | 119.2 | C(9)—C(10)—C(11) | 120.7 (2) |
C(3)—C(2)—H(2) | 119.2 | C(9)—C(10)—H(10) | 119.7 |
O—C(3)—C(2) | 105.28 (16) | C(11)—C(10)—H(10) | 119.7 |
O—C(3)—H(3A) | 110.7 | C(10)—C(11)—C(6) | 120.4 (2) |
C(2)—C(3)—H(3A) | 110.7 | C(10)—C(11)—H(11) | 119.8 |
O—C(3)—H(3B) | 110.7 | C(6)—C(11)—H(11) | 119.8 |
C(2)—C(3)—H(3B) | 110.7 | N(2)—C(12)—B | 179.8 (2) |
H(3A)—C(3)—H(3B) | 108.8 | N(3)—C(13)—B | 178.1 (2) |
N(1)—C(4)—C(6) | 111.54 (14) | O—B—C(13) | 110.71 (16) |
N(1)—C(4)—C(5) | 108.54 (16) | O—B—N(1) | 104.08 (14) |
C(6)—C(4)—C(5) | 114.35 (16) | C(13)—B—N(1) | 112.53 (15) |
N(1)—C(4)—H(4) | 107.4 | O—B—C(12) | 114.09 (16) |
C(6)—C(4)—H(4) | 107.4 | C(13)—B—C(12) | 109.59 (15) |
C(5)—C(4)—H(4) | 107.4 | N(1)—B—C(12) | 105.71 (15) |
C(4)—C(5)—H(5A) | 109.5 | C(1)—N(1)—C(2) | 58.81 (13) |
C(4)—C(5)—H(5B) | 109.5 | C(1)—N(1)—C(4) | 118.49 (14) |
H(5A)—C(5)—H(5B) | 109.5 | C(2)—N(1)—C(4) | 123.43 (14) |
C(4)—C(5)—H(5C) | 109.5 | C(1)—N(1)—B | 113.35 (15) |
H(5A)—C(5)—H(5C) | 109.5 | C(2)—N(1)—B | 102.86 (14) |
H(5B)—C(5)—H(5C) | 109.5 | C(4)—N(1)—B | 122.79 (14) |
C(11)—C(6)—C(7) | 118.8 (2) | B—O—C(3) | 107.80 (15) |
C(11)—C(6)—C(4) | 118.59 (19) | | |
| | | |
N1—C1—C2—C3 | 94.14 (17) | C1—C2—N1—B | 109.70 (15) |
C1—C2—C3—O | −40.6 (2) | C3—C2—N1—B | −2.95 (17) |
N1—C2—C3—O | 23.63 (19) | C6—C4—N1—C1 | −57.9 (2) |
N1—C4—C6—C11 | −86.3 (2) | C5—C4—N1—C1 | 69.0 (2) |
C5—C4—C6—C11 | 150.03 (18) | C6—C4—N1—C2 | 11.8 (2) |
N1—C4—C6—C7 | 91.6 (2) | C5—C4—N1—C2 | 138.65 (16) |
C5—C4—C6—C7 | −32.0 (2) | C6—C4—N1—B | 149.74 (15) |
C11—C6—C7—C8 | 0.6 (3) | C5—C4—N1—B | −83.40 (19) |
C4—C6—C7—C8 | −177.40 (17) | O—B—N1—C1 | 42.79 (19) |
C6—C7—C8—C9 | 0.9 (3) | C13—B—N1—C1 | −77.12 (19) |
C7—C8—C9—C10 | −0.9 (4) | C12—B—N1—C1 | 163.30 (15) |
C8—C9—C10—C11 | −0.5 (4) | O—B—N1—C2 | −18.52 (16) |
C9—C10—C11—C6 | 1.9 (4) | C13—B—N1—C2 | −138.43 (16) |
C7—C6—C11—C10 | −2.0 (3) | C12—B—N1—C2 | 101.99 (16) |
C4—C6—C11—C10 | 176.1 (2) | O—B—N1—C4 | −163.54 (14) |
N3—C13—B—O | 44 (7) | C13—B—N1—C4 | 76.5 (2) |
N3—C13—B—N1 | 160 (6) | C12—B—N1—C4 | −43.0 (2) |
N3—C13—B—C12 | −83 (7) | C13—B—O—C3 | 155.89 (15) |
N2—C12—B—O | 154 (100) | N1—B—O—C3 | 34.75 (18) |
N2—C12—B—C13 | −81 (67) | C12—B—O—C3 | −79.94 (18) |
N2—C12—B—N1 | 40 (67) | C2—C3—O—B | −37.3 (2) |
C2—C1—N1—C4 | 113.84 (17) | C1—C2—N1—B | 109.70 (15) |
C2—C1—N1—B | −91.26 (16) | C1—C2—N1—C3 | 112.66 (17) |
C3—C2—N1—C1 | −112.66 (17) | O—B—C3—N1 | 144.92 (19) |
C1—C2—N1—C4 | −105.57 (17) | O—B—C3—C2 | 143.0 (2) |
C3—C2—N1—C4 | 141.77 (16) | | |
Symmetry code: (i) x+1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···N3i | 0.97 | 2.92 | 3.163 (4) | 95 |
C2—H2···N2i | 0.98 | 2.67 | 3.465 (3) | 138 |
C1—H1B···N2ii | 0.97 | 2.64 | 3.404 (3) | 136 |
C9—H9···N3iii | 0.93 | 2.70 | 3.553 (4) | 152 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z; (iii) x+1, y+1, z−1. |
Experimental details
Crystal data |
Chemical formula | C13H14BN3O |
Mr | 239.08 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 6.710 (3), 6.767 (4), 8.059 (5) |
α, β, γ (°) | 71.51 (4), 84.68 (5), 70.16 (3) |
V (Å3) | 326.4 (3) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.5 × 0.4 × 0.3 |
|
Data collection |
Diffractometer | MacScience MXC3 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1595, 1483, 1435 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.033, 0.090, 1.08 |
No. of reflections | 1483 |
No. of parameters | 165 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.15 |
Selected geometric parameters (Å, º) topC(1)—C(2) | 1.468 (3) | C(12)—B | 1.618 (3) |
C(1)—N(1) | 1.484 (2) | C(13)—N(3) | 1.128 (3) |
C(2)—N(1) | 1.506 (2) | C(13)—B | 1.604 (3) |
C(2)—C(3) | 1.513 (3) | B—O | 1.425 (3) |
C(3)—O | 1.427 (3) | B—N(1) | 1.608 (3) |
C(12)—N(2) | 1.140 (3) | | |
| | | |
C(2)—C(1)—N(1) | 61.34 (12) | N(1)—B—C(12) | 105.71 (15) |
C(1)—C(2)—N(1) | 59.85 (12) | C(1)—N(1)—C(2) | 58.81 (13) |
N(2)—C(12)—B | 179.8 (2) | C(1)—N(1)—C(4) | 118.49 (14) |
N(3)—C(13)—B | 178.1 (2) | C(2)—N(1)—C(4) | 123.43 (14) |
O—B—C(13) | 110.71 (16) | C(1)—N(1)—B | 113.35 (15) |
O—B—N(1) | 104.08 (14) | C(2)—N(1)—B | 102.86 (14) |
C(13)—B—N(1) | 112.53 (15) | C(4)—N(1)—B | 122.79 (14) |
O—B—C(12) | 114.09 (16) | B—O—C(3) | 107.80 (15) |
C(13)—B—C(12) | 109.59 (15) | | |
| | | |
C1—C2—C3—O | −40.6 (2) | O—B—N1—C2 | −18.52 (16) |
N1—C2—C3—O | 23.63 (19) | O—B—N1—C4 | −163.54 (14) |
O—B—N1—C1 | 42.79 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···N2i | 0.98 | 2.67 | 3.465 (3) | 138.3 |
C1—H1B···N2ii | 0.97 | 2.64 | 3.404 (3) | 135.8 |
C9—H9···N3iii | 0.93 | 2.70 | 3.553 (4) | 152.3 |
Symmetry codes: (i) x+1, y, z; (ii) x+1, y−1, z; (iii) x+1, y+1, z−1. |
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During the course of the synthetic studies using the chiral aziridine 1-[(S)-1-phenylethyl]-2 − t-butyldimethylsilyloxymethylaziridine (Lee & Ha, 2003), we expected that the azidirine ring, known to be labile to Lewis acids (Pearson et al., 1996), would be opened by a nitrile nucleophile with the assistance of boron trifluoride. However, although the spectral data for the product, viz. the title compound, (I), do not allow an unambiguous structural assignment, they clearly show that (I) contains two cyano groups, with conservation of the three-membered aziridine ring, known to be labile with Lewis acids (Pearson, et al., 1996). Compound (I) is stable at room temperature in air for up to a month, and the structure determination described here was undertaken to establish its exact nature.
The structure of (I) is shown in Fig. 1. Contrary to our expectation, the nitrile nucleophiles have replaced the fluorides at the B atom instead of leading to ring opening, and the aziridine ring remains intact. Atoms N1, C1 and C2 form an almost equilateral triangle, the C1—C2 distance [1.468 (3) Å] being slightly shorter than the C—N distances [1.484 (2) and 1.506 (2) Å]. Usually, the C—C distances in aziridine rings are longer than the C—N distances (Hargreaves et al., 1997; Willems et al., 1997). However, the C—N bond distances in (I) are slightly longer than the C—C distances. This behaviour is probably due to the electron-donating nature of the N atom towards the B atom in forming the dative B—N bond. The geometry around atom N1 is distorted significantly from the ideal tetrahedron, with high strain.
A five-membered ring composed of atoms N1, B, O, C3 and C2 is observed in the product. This ring is fused with the aziridine ring, thus forming a six-membered ring that displays a chair conformation. The interplanar angle between the azidirine ring plane and the main plane of the chair (B/N1/C2/C3) is 68.96 (12)°, which is greater than that to the plane composed of atoms O, B and C3 [35.98 (17)°].
Compound (I) has a characteristic coordinative bond between the N and B atoms, with a bond distance of 1.608 (3) Å, which is significantly longer than the usual covalent bond distances (~1.4 Å; Allen et al., 1987) but agrees well with values for other dative B—N bonds, e.g. in NH3BF3 (Penner et al., 2002). The geometry around the B atom can be described as typical of tetrahedral coordination [ca 104.1 (1)–114.1 (2) °].
There is no strong hydrogen bond in (I) (Spek, 1990). However, there are some short C—H···N contacts that could be regarded as weak hydrogen bonds (Table 2). Additionally, there is an intermolecular contact between atoms C1 and N3(1 + x,y,z) [3.163 (4) Å].