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The title compound, alternatively known as benzodi­aza­borole trimer, C18H15B3N6·2C3H6O, at 100 K crystallizes in the triclinic system, space group P\overline{1}. The structure displays N—H...O hydrogen bonding connecting the main mol­ecule with the crystallization solvent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989023009337/ex2077sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989023009337/ex2077Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989023009337/ex2077Isup3.cml
Supplementary material

CCDC reference: 2303332

Computing details top

Data collection: APEX4 Ver. 8.38A (Bruker, 2022); cell refinement: SAINT-Plus V8.40B (Bruker, 2020); data reduction: SAINT-Plus Ve8.40B (Bruker, 2020); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL209/1 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Triazatriborinotris[1,3,2]benzodiazaborole acetone disolvate top
Crystal data top
C18H15B3N6·2C3H6OZ = 2
Mr = 463.94F(000) = 488
Triclinic, P1Dx = 1.296 Mg m3
a = 5.8357 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.6362 (9) ÅCell parameters from 9824 reflections
c = 15.4653 (10) Åθ = 3.3–74.3°
α = 97.595 (3)°µ = 0.66 mm1
β = 96.957 (3)°T = 100 K
γ = 99.771 (3)°Rod, colourless
V = 1189.13 (14) Å30.41 × 0.13 × 0.13 mm
Data collection top
Bruker D8 Venture
diffractometer
4853 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec IµS 3.04226 reflections with I > 2σ(I)
Multilayer mirror monochromatorRint = 0.040
Detector resolution: 7.9 pixels mm-1θmax = 74.6°, θmin = 2.9°
ω and φ scansh = 77
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1717
Tmin = 0.699, Tmax = 0.754l = 1919
47276 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0377P)2 + 0.3978P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4853 reflectionsΔρmax = 0.22 e Å3
579 parametersΔρmin = 0.23 e Å3
369 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.

Refinement. All nonhydrogen atoms were located in a series of difference Fourier electron density maps and refined using anisotropic displacement parameters. All C-H hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv of the connected C atoms 1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen were located in Fourier diff maps. A RIGU command was applied to the minor component and ISOR to N2A, N4A, and N6A. The N-H bonds were restrained with the SADI command. The benzodiazaborole molecule was modeled with two-part disorder with occupancy factors refined to 89:11. The minor restrained using the SAME and RIGU commands. N2A, N4A, N6A were also restrained with an ISOR comand. The locations NH hydrogen atoms of the minor componenent were were fixed using AFIX 43 commands.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O11.06089 (19)0.80696 (9)0.44502 (7)0.0509 (3)
C191.4443 (2)0.84484 (11)0.52511 (9)0.0394 (3)
H19A1.4658840.9005880.4910550.059*
H19B1.5664860.8046330.5170580.059*
H19C1.4557420.8718850.5877460.059*
C201.2081 (2)0.78000 (10)0.49384 (8)0.0292 (3)
C211.1621 (3)0.68044 (11)0.52471 (10)0.0414 (3)
H21A0.9923120.6548470.5164800.062*
H21B1.2257950.6882000.5873620.062*
H21C1.2380690.6328120.4905870.062*
O20.42413 (17)0.45535 (8)0.15098 (7)0.0438 (3)
C220.7168 (3)0.31164 (10)0.15045 (10)0.0444 (4)
H22A0.7466140.2602530.0976820.067*
H22B0.8634790.3140310.1748050.067*
H22C0.6005410.2947810.1945620.067*
C230.6251 (2)0.41159 (9)0.12665 (8)0.0307 (3)
C240.7921 (3)0.45521 (12)0.06874 (11)0.0502 (4)
H24A0.9117860.4767030.1023290.075*
H24B0.8683430.4041660.0181790.075*
H24C0.7058550.5133640.0477170.075*
N10.05231 (18)0.94365 (8)0.12177 (7)0.0213 (2)0.8922 (14)
H10.087 (3)1.0065 (10)0.1141 (10)0.026*0.8922 (14)
N20.0215 (2)0.79057 (11)0.17389 (8)0.0199 (3)0.8922 (14)
N30.01420 (19)0.61709 (8)0.23107 (7)0.0223 (2)0.8922 (14)
H30.155 (2)0.5811 (11)0.2091 (10)0.027*0.8922 (14)
N40.3305 (3)0.73686 (10)0.27224 (7)0.0199 (3)0.8922 (14)
N50.70842 (18)0.87612 (8)0.32562 (7)0.0217 (2)0.8922 (14)
H50.808 (2)0.8516 (11)0.3595 (9)0.026*0.8922 (14)
N60.3973 (2)0.90929 (9)0.23233 (8)0.0194 (2)0.8922 (14)
C10.1652 (3)0.88371 (13)0.08577 (11)0.0198 (3)0.8922 (14)
C20.3450 (4)0.90431 (14)0.02761 (13)0.0224 (4)0.8922 (14)
H20.3296780.9663650.0052660.027*0.8922 (14)
C30.5501 (3)0.83056 (16)0.00289 (13)0.0229 (4)0.8922 (14)
H3A0.6767210.8431840.0361310.027*0.8922 (14)
C40.5705 (3)0.73916 (13)0.03476 (11)0.0229 (4)0.8922 (14)
H40.7108250.6902460.0171420.027*0.8922 (14)
C50.3876 (3)0.71828 (12)0.09227 (10)0.0212 (3)0.8922 (14)
H5A0.4017020.6557860.1138580.025*0.8922 (14)
C60.1858 (3)0.79089 (14)0.11696 (8)0.0191 (3)0.8922 (14)
C70.1469 (3)0.57793 (15)0.28473 (8)0.0208 (3)0.8922 (14)
C80.1229 (3)0.48537 (15)0.31331 (13)0.0244 (4)0.8922 (14)
H80.0206500.4380140.2982630.029*0.8922 (14)
C90.3158 (4)0.46330 (17)0.36499 (18)0.0260 (5)0.8922 (14)
H90.3036140.4001220.3853240.031*0.8922 (14)
C100.5261 (3)0.53338 (15)0.38692 (12)0.0251 (4)0.8922 (14)
H100.6560800.5166690.4212370.030*0.8922 (14)
C110.5489 (3)0.62773 (11)0.35930 (10)0.0227 (3)0.8922 (14)
H110.6918150.6754310.3747470.027*0.8922 (14)
C120.3572 (3)0.64948 (10)0.30890 (10)0.0199 (3)0.8922 (14)
C130.7668 (4)0.97371 (11)0.30686 (11)0.0215 (3)0.8922 (14)
C140.9721 (4)1.04497 (16)0.33531 (14)0.0244 (4)0.8922 (14)
H141.0979071.0310740.3739270.029*0.8922 (14)
C150.9867 (4)1.13764 (18)0.30511 (17)0.0262 (5)0.8922 (14)
H151.1253641.1874610.3229800.031*0.8922 (14)
C160.8000 (3)1.15820 (13)0.24893 (11)0.0266 (4)0.8922 (14)
H160.8139591.2217620.2292320.032*0.8922 (14)
C170.5933 (3)1.08661 (14)0.22134 (9)0.0240 (3)0.8922 (14)
H170.4661361.1009740.1837330.029*0.8922 (14)
C180.5792 (2)0.99461 (14)0.25019 (10)0.0200 (3)0.8922 (14)
B10.1734 (3)0.88827 (13)0.17792 (10)0.0203 (3)0.8922 (14)
B20.0951 (3)0.71571 (12)0.22164 (12)0.0206 (3)0.8922 (14)
B30.4808 (3)0.83321 (14)0.27939 (10)0.0202 (3)0.8922 (14)
N1A0.1999 (13)0.6816 (6)0.1539 (5)0.0194 (17)0.1078 (14)
H1A0.282 (18)0.623 (4)0.158 (8)0.023*0.1078 (14)
N2A0.0651 (16)0.8336 (8)0.1694 (6)0.0115 (18)0.1078 (14)
N3A0.3577 (13)1.0072 (6)0.1865 (5)0.0199 (17)0.1078 (14)
H3AA0.2829221.0419250.1522820.024*0.1078 (14)
N4A0.4546 (15)0.8803 (7)0.2592 (6)0.0101 (16)0.1078 (14)
N5A0.5854 (14)0.7321 (6)0.3329 (6)0.0202 (18)0.1078 (14)
H5AA0.722 (10)0.736 (9)0.366 (7)0.024*0.1078 (14)
N6A0.2152 (19)0.7135 (6)0.2538 (6)0.0106 (17)0.1078 (14)
C1A0.290 (2)0.7472 (10)0.1031 (7)0.014 (2)0.1078 (14)
C2A0.506 (3)0.7254 (10)0.0533 (11)0.022 (3)0.1078 (14)
H2A0.6099290.6633750.0521680.026*0.1078 (14)
C3A0.568 (3)0.7960 (12)0.0050 (13)0.022 (3)0.1078 (14)
H3AB0.7155530.7832900.0318000.026*0.1078 (14)
C4A0.417 (3)0.8847 (12)0.0099 (11)0.017 (3)0.1078 (14)
H4A0.4634780.9334620.0236470.021*0.1078 (14)
C5A0.201 (2)0.9069 (10)0.0609 (9)0.014 (2)0.1078 (14)
H5AB0.0966610.9689710.0624660.017*0.1078 (14)
C6A0.1419 (18)0.8371 (10)0.1089 (7)0.013 (2)0.1078 (14)
C7A0.5800 (17)1.0397 (11)0.2354 (8)0.018 (2)0.1078 (14)
C8A0.720 (3)1.1301 (10)0.2390 (10)0.025 (3)0.1078 (14)
H8A0.6709041.1789490.2062660.030*0.1078 (14)
C9A0.935 (3)1.1498 (14)0.2911 (15)0.020 (3)0.1078 (14)
H9A1.0368521.2134020.2966350.025*0.1078 (14)
C10A1.000 (3)1.0759 (13)0.3346 (15)0.025 (4)0.1078 (14)
H10A1.1519471.0893070.3685720.030*0.1078 (14)
C11A0.860 (2)0.9829 (10)0.3327 (9)0.020 (3)0.1078 (14)
H11A0.9086250.9338010.3654010.024*0.1078 (14)
C12A0.647 (2)0.9667 (8)0.2801 (8)0.012 (2)0.1078 (14)
C13A0.462 (2)0.6377 (8)0.3348 (8)0.015 (2)0.1078 (14)
C14A0.542 (2)0.5652 (11)0.3771 (11)0.018 (3)0.1078 (14)
H14A0.6971820.5748820.4078140.022*0.1078 (14)
C15A0.382 (3)0.4774 (15)0.3719 (16)0.019 (3)0.1078 (14)
H15A0.4296360.4255140.4009100.022*0.1078 (14)
C16A0.156 (3)0.4599 (12)0.3273 (13)0.020 (3)0.1078 (14)
H16A0.0538940.3972670.3257900.023*0.1078 (14)
C17A0.077 (2)0.5340 (10)0.2846 (8)0.016 (2)0.1078 (14)
H17A0.0774680.5244710.2535390.019*0.1078 (14)
C18A0.236 (2)0.6213 (8)0.2900 (6)0.0082 (18)0.1078 (14)
B1A0.0310 (19)0.7366 (9)0.1970 (8)0.011 (2)0.1078 (14)
B2A0.273 (2)0.9081 (8)0.2018 (8)0.010 (2)0.1078 (14)
B3A0.434 (2)0.7822 (9)0.2840 (7)0.012 (2)0.1078 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0489 (6)0.0642 (7)0.0388 (6)0.0269 (5)0.0118 (5)0.0005 (5)
C190.0371 (7)0.0432 (8)0.0344 (7)0.0001 (6)0.0072 (6)0.0006 (6)
C200.0295 (6)0.0356 (7)0.0227 (6)0.0107 (5)0.0019 (5)0.0010 (5)
C210.0511 (9)0.0364 (8)0.0373 (7)0.0044 (6)0.0156 (6)0.0045 (6)
O20.0341 (5)0.0417 (6)0.0466 (6)0.0080 (4)0.0031 (4)0.0040 (5)
C220.0566 (9)0.0283 (7)0.0492 (9)0.0015 (6)0.0233 (7)0.0035 (6)
C230.0324 (7)0.0251 (6)0.0322 (6)0.0013 (5)0.0069 (5)0.0012 (5)
C240.0539 (9)0.0412 (8)0.0520 (9)0.0131 (7)0.0053 (7)0.0006 (7)
N10.0204 (5)0.0182 (5)0.0245 (5)0.0017 (4)0.0015 (4)0.0043 (4)
N20.0173 (6)0.0192 (7)0.0226 (6)0.0017 (5)0.0019 (4)0.0048 (6)
N30.0193 (5)0.0217 (5)0.0252 (5)0.0017 (4)0.0012 (4)0.0053 (4)
N40.0181 (7)0.0201 (6)0.0214 (6)0.0023 (5)0.0016 (5)0.0060 (5)
N50.0202 (5)0.0221 (5)0.0223 (5)0.0028 (4)0.0002 (4)0.0059 (4)
N60.0192 (6)0.0189 (6)0.0199 (6)0.0024 (5)0.0020 (5)0.0046 (5)
C10.0204 (7)0.0201 (9)0.0195 (8)0.0055 (6)0.0033 (6)0.0026 (6)
C20.0201 (10)0.0215 (8)0.0243 (9)0.0029 (7)0.0014 (8)0.0020 (7)
C30.0217 (8)0.0249 (10)0.0222 (7)0.0059 (8)0.0005 (6)0.0044 (8)
C40.0214 (8)0.0254 (9)0.0202 (8)0.0029 (6)0.0002 (6)0.0021 (6)
C50.0205 (8)0.0208 (7)0.0211 (7)0.0023 (6)0.0015 (6)0.0019 (6)
C60.0182 (7)0.0195 (8)0.0194 (6)0.0035 (6)0.0032 (5)0.0018 (6)
C70.0237 (8)0.0186 (8)0.0204 (7)0.0028 (7)0.0057 (6)0.0030 (7)
C80.0270 (8)0.0225 (10)0.0244 (10)0.0037 (7)0.0053 (7)0.0055 (7)
C90.0331 (13)0.0193 (9)0.0262 (10)0.0025 (8)0.0060 (10)0.0074 (8)
C100.0303 (9)0.0230 (10)0.0238 (8)0.0078 (8)0.0024 (6)0.0078 (7)
C110.0245 (7)0.0227 (8)0.0216 (7)0.0056 (6)0.0029 (6)0.0053 (6)
C120.0209 (8)0.0202 (7)0.0190 (7)0.0038 (6)0.0039 (6)0.0042 (5)
C130.0191 (9)0.0231 (7)0.0203 (8)0.0005 (7)0.0031 (7)0.0006 (6)
C140.0232 (9)0.0224 (10)0.0262 (8)0.0010 (8)0.0030 (7)0.0038 (9)
C150.0234 (10)0.0245 (10)0.0272 (11)0.0020 (7)0.0003 (7)0.0029 (7)
C160.0271 (9)0.0217 (8)0.0276 (8)0.0034 (7)0.0022 (7)0.0036 (6)
C170.0250 (8)0.0213 (8)0.0235 (7)0.0003 (6)0.0013 (5)0.0035 (6)
C180.0205 (7)0.0196 (8)0.0194 (7)0.0022 (6)0.0035 (5)0.0024 (6)
B10.0207 (8)0.0208 (8)0.0192 (7)0.0031 (7)0.0041 (6)0.0017 (6)
B20.0195 (9)0.0227 (8)0.0200 (8)0.0040 (6)0.0038 (7)0.0037 (6)
B30.0225 (7)0.0204 (9)0.0190 (7)0.0049 (7)0.0056 (5)0.0049 (7)
N1A0.018 (3)0.016 (3)0.022 (3)0.001 (2)0.006 (2)0.007 (3)
N2A0.011 (3)0.007 (3)0.015 (3)0.001 (2)0.007 (2)0.008 (2)
N3A0.019 (3)0.014 (3)0.024 (4)0.002 (2)0.000 (3)0.006 (2)
N4A0.007 (3)0.008 (3)0.013 (3)0.0032 (19)0.004 (2)0.005 (2)
N5A0.016 (3)0.018 (3)0.026 (4)0.001 (2)0.002 (2)0.010 (3)
N6A0.008 (3)0.007 (3)0.015 (3)0.002 (2)0.005 (2)0.005 (2)
C1A0.010 (3)0.010 (4)0.017 (4)0.004 (2)0.007 (3)0.005 (3)
C2A0.016 (4)0.014 (4)0.029 (6)0.006 (3)0.014 (3)0.011 (4)
C3A0.014 (4)0.020 (5)0.028 (6)0.002 (4)0.008 (3)0.012 (5)
C4A0.009 (4)0.016 (5)0.027 (6)0.004 (3)0.007 (3)0.012 (4)
C5A0.009 (4)0.014 (4)0.020 (5)0.005 (3)0.003 (3)0.010 (3)
C6A0.010 (3)0.007 (4)0.020 (4)0.002 (2)0.009 (3)0.007 (3)
C7A0.015 (3)0.011 (3)0.024 (5)0.004 (3)0.003 (3)0.007 (3)
C8A0.020 (4)0.014 (4)0.034 (6)0.009 (3)0.005 (4)0.007 (3)
C9A0.019 (5)0.014 (5)0.025 (6)0.008 (3)0.000 (4)0.004 (4)
C10A0.015 (4)0.017 (5)0.036 (7)0.012 (3)0.005 (4)0.008 (5)
C11A0.010 (4)0.018 (4)0.026 (5)0.008 (3)0.005 (3)0.005 (4)
C12A0.008 (3)0.010 (3)0.016 (4)0.004 (2)0.001 (3)0.003 (3)
C13A0.009 (4)0.016 (3)0.021 (5)0.001 (2)0.005 (3)0.011 (3)
C14A0.016 (4)0.015 (4)0.022 (5)0.001 (3)0.007 (3)0.010 (4)
C15A0.018 (5)0.016 (4)0.022 (6)0.003 (3)0.004 (4)0.010 (4)
C16A0.021 (5)0.014 (4)0.024 (6)0.003 (3)0.003 (4)0.012 (4)
C17A0.016 (4)0.011 (4)0.020 (5)0.000 (3)0.001 (3)0.010 (3)
C18A0.008 (3)0.008 (3)0.009 (4)0.001 (2)0.001 (3)0.004 (3)
B1A0.011 (3)0.008 (3)0.013 (4)0.001 (2)0.003 (3)0.006 (3)
B2A0.008 (3)0.008 (3)0.013 (4)0.001 (2)0.003 (3)0.004 (2)
B3A0.009 (3)0.009 (3)0.016 (4)0.003 (2)0.004 (3)0.005 (3)
Geometric parameters (Å, º) top
O1—C201.2110 (15)C13—C181.410 (2)
C19—H19A0.9800C14—H140.9500
C19—H19B0.9800C14—C151.397 (2)
C19—H19C0.9800C15—H150.9500
C19—C201.4927 (18)C15—C161.400 (2)
C20—C211.4906 (19)C16—H160.9500
C21—H21A0.9800C16—C171.398 (2)
C21—H21B0.9800C17—H170.9500
C21—H21C0.9800C17—C181.379 (2)
O2—C231.2122 (16)N1A—H1A0.880 (18)
C22—H22A0.9800N1A—C1A1.391 (11)
C22—H22B0.9800N1A—B1A1.460 (12)
C22—H22C0.9800N2A—C6A1.447 (11)
C22—C231.4873 (18)N2A—B1A1.433 (12)
C23—C241.494 (2)N2A—B2A1.433 (12)
C24—H24A0.9800N3A—H3AA0.8800
C24—H24B0.9800N3A—C7A1.389 (11)
C24—H24C0.9800N3A—B2A1.419 (11)
N1—H10.874 (12)N4A—C12A1.454 (11)
N1—C11.3948 (18)N4A—B2A1.433 (13)
N1—B11.4247 (19)N4A—B3A1.429 (12)
N2—C61.4082 (17)N5A—H5AA0.883 (18)
N2—B11.459 (2)N5A—C13A1.370 (11)
N2—B21.429 (2)N5A—B3A1.414 (11)
N3—H30.886 (12)N6A—C18A1.459 (11)
N3—C71.3985 (17)N6A—B1A1.409 (12)
N3—B21.4212 (19)N6A—B3A1.435 (12)
N4—C121.4091 (18)C1A—C2A1.362 (13)
N4—B21.459 (2)C1A—C6A1.359 (13)
N4—B31.433 (2)C2A—H2A0.9500
N5—H50.871 (12)C2A—C3A1.363 (14)
N5—C131.3941 (17)C3A—H3AB0.9500
N5—B31.4191 (18)C3A—C4A1.356 (14)
N6—C181.4077 (18)C4A—H4A0.9500
N6—B11.428 (2)C4A—C5A1.369 (13)
N6—B31.459 (2)C5A—H5AB0.9500
C1—C21.388 (2)C5A—C6A1.346 (12)
C1—C61.405 (2)C7A—C8A1.349 (13)
C2—H20.9500C7A—C12A1.367 (13)
C2—C31.403 (2)C8A—H8A0.9500
C3—H3A0.9500C8A—C9A1.371 (15)
C3—C41.392 (2)C9A—H9A0.9500
C4—H40.9500C9A—C10A1.363 (15)
C4—C51.397 (2)C10A—H10A0.9500
C5—H5A0.9500C10A—C11A1.382 (13)
C5—C61.382 (2)C11A—H11A0.9500
C7—C81.382 (3)C11A—C12A1.370 (13)
C7—C121.409 (2)C13A—C14A1.369 (14)
C8—H80.9500C13A—C18A1.382 (13)
C8—C91.399 (3)C14A—H14A0.9500
C9—H90.9500C14A—C15A1.375 (15)
C9—C101.396 (2)C15A—H15A0.9500
C10—H100.9500C15A—C16A1.378 (15)
C10—C111.399 (2)C16A—H16A0.9500
C11—H110.9500C16A—C17A1.387 (12)
C11—C121.382 (2)C17A—H17A0.9500
C13—C141.392 (3)C17A—C18A1.365 (13)
H19A—C19—H19B109.5C16—C17—H17120.9
H19A—C19—H19C109.5C18—C17—C16118.20 (14)
H19B—C19—H19C109.5C18—C17—H17120.9
C20—C19—H19A109.5N6—C18—C13108.64 (17)
C20—C19—H19B109.5C17—C18—N6130.44 (16)
C20—C19—H19C109.5C17—C18—C13120.92 (13)
O1—C20—C19121.34 (13)N1—B1—N2107.25 (15)
O1—C20—C21121.53 (13)N1—B1—N6133.95 (16)
C21—C20—C19117.12 (12)N6—B1—N2118.79 (13)
C20—C21—H21A109.5N2—B2—N4118.80 (13)
C20—C21—H21B109.5N3—B2—N2133.35 (16)
C20—C21—H21C109.5N3—B2—N4107.85 (15)
H21A—C21—H21B109.5N4—B3—N6118.71 (12)
H21A—C21—H21C109.5N5—B3—N4133.60 (16)
H21B—C21—H21C109.5N5—B3—N6107.68 (14)
H22A—C22—H22B109.5C1A—N1A—H1A122 (8)
H22A—C22—H22C109.5C1A—N1A—B1A105.0 (9)
H22B—C22—H22C109.5B1A—N1A—H1A133 (8)
C23—C22—H22A109.5B1A—N2A—C6A107.3 (9)
C23—C22—H22B109.5B1A—N2A—B2A121.9 (9)
C23—C22—H22C109.5B2A—N2A—C6A130.8 (9)
O2—C23—C22122.38 (13)C7A—N3A—H3AA126.2
O2—C23—C24120.99 (13)C7A—N3A—B2A107.6 (10)
C22—C23—C24116.61 (13)B2A—N3A—H3AA126.2
C23—C24—H24A109.5B2A—N4A—C12A106.9 (9)
C23—C24—H24B109.5B3A—N4A—C12A130.8 (10)
C23—C24—H24C109.5B3A—N4A—B2A122.2 (8)
H24A—C24—H24B109.5C13A—N5A—H5AA106 (8)
H24A—C24—H24C109.5C13A—N5A—B3A107.1 (9)
H24B—C24—H24C109.5B3A—N5A—H5AA147 (8)
C1—N1—H1121.2 (10)B1A—N6A—C18A130.6 (10)
C1—N1—B1107.84 (14)B1A—N6A—B3A122.9 (9)
B1—N1—H1130.4 (10)B3A—N6A—C18A106.5 (9)
C6—N2—B1106.69 (14)C2A—C1A—N1A123.9 (12)
C6—N2—B2132.10 (15)C6A—C1A—N1A113.6 (10)
B2—N2—B1121.21 (13)C6A—C1A—C2A122.5 (10)
C7—N3—H3121.0 (10)C1A—C2A—H2A121.3
C7—N3—B2107.62 (14)C1A—C2A—C3A117.3 (12)
B2—N3—H3131.4 (10)C3A—C2A—H2A121.3
C12—N4—B2106.30 (14)C2A—C3A—H3AB120.2
C12—N4—B3132.59 (15)C4A—C3A—C2A119.7 (13)
B3—N4—B2121.07 (12)C4A—C3A—H3AB120.2
C13—N5—H5120.5 (10)C3A—C4A—H4A118.6
C13—N5—B3107.76 (14)C3A—C4A—C5A122.8 (14)
B3—N5—H5131.7 (10)C5A—C4A—H4A118.6
C18—N6—B1132.24 (15)C4A—C5A—H5AB121.4
C18—N6—B3106.46 (14)C6A—C5A—C4A117.2 (13)
B1—N6—B3121.25 (12)C6A—C5A—H5AB121.4
N1—C1—C6109.50 (16)C1A—C6A—N2A106.6 (10)
C2—C1—N1129.53 (19)C5A—C6A—N2A132.9 (12)
C2—C1—C6120.97 (15)C5A—C6A—C1A120.4 (10)
C1—C2—H2121.1C8A—C7A—N3A126.1 (13)
C1—C2—C3117.88 (17)C8A—C7A—C12A122.4 (10)
C3—C2—H2121.1C12A—C7A—N3A111.4 (11)
C2—C3—H3A119.6C7A—C8A—H8A120.7
C4—C3—C2120.88 (17)C7A—C8A—C9A118.5 (12)
C4—C3—H3A119.6C9A—C8A—H8A120.7
C3—C4—H4119.5C8A—C9A—H9A120.9
C3—C4—C5120.98 (16)C10A—C9A—C8A118.3 (15)
C5—C4—H4119.5C10A—C9A—H9A120.9
C4—C5—H5A120.9C9A—C10A—H10A117.7
C6—C5—C4118.26 (14)C9A—C10A—C11A124.6 (16)
C6—C5—H5A120.9C11A—C10A—H10A117.7
C1—C6—N2108.71 (16)C10A—C11A—H11A122.5
C5—C6—N2130.27 (16)C12A—C11A—C10A115.0 (13)
C5—C6—C1121.01 (13)C12A—C11A—H11A122.5
N3—C7—C12109.33 (17)C7A—C12A—N4A106.8 (11)
C8—C7—N3129.57 (19)C7A—C12A—C11A121.1 (10)
C8—C7—C12121.10 (15)C11A—C12A—N4A132.1 (12)
C7—C8—H8120.9N5A—C13A—C18A112.6 (11)
C7—C8—C9118.21 (18)C14A—C13A—N5A126.2 (13)
C9—C8—H8120.9C14A—C13A—C18A121.1 (9)
C8—C9—H9119.7C13A—C14A—H14A122.4
C10—C9—C8120.5 (2)C13A—C14A—C15A115.3 (12)
C10—C9—H9119.7C15A—C14A—H14A122.4
C9—C10—H10119.4C14A—C15A—H15A117.9
C9—C10—C11121.24 (18)C14A—C15A—C16A124.2 (16)
C11—C10—H10119.4C16A—C15A—H15A117.9
C10—C11—H11121.0C15A—C16A—H16A120.1
C12—C11—C10118.00 (15)C15A—C16A—C17A119.9 (15)
C12—C11—H11121.0C17A—C16A—H16A120.1
C7—C12—N4108.88 (17)C16A—C17A—H17A122.0
C11—C12—N4130.22 (16)C18A—C17A—C16A116.0 (12)
C11—C12—C7120.88 (13)C18A—C17A—H17A122.0
N5—C13—C18109.44 (17)C13A—C18A—N6A105.6 (10)
C14—C13—N5129.36 (19)C17A—C18A—N6A130.9 (12)
C14—C13—C18121.20 (15)C17A—C18A—C13A123.5 (9)
C13—C14—H14121.2N2A—B1A—N1A107.4 (9)
C13—C14—C15117.67 (18)N6A—B1A—N1A134.6 (11)
C15—C14—H14121.2N6A—B1A—N2A118.0 (9)
C14—C15—H15119.5N2A—B2A—N4A117.6 (8)
C14—C15—C16121.0 (2)N3A—B2A—N2A135.0 (11)
C16—C15—H15119.5N3A—B2A—N4A107.2 (9)
C15—C16—H16119.5N4A—B3A—N6A117.2 (8)
C17—C16—C15121.01 (17)N5A—B3A—N4A134.7 (10)
C17—C16—H16119.5N5A—B3A—N6A108.1 (9)
N1—C1—C2—C3178.74 (15)N1A—C1A—C2A—C3A178.3 (14)
N1—C1—C6—N20.09 (15)N1A—C1A—C6A—N2A0.7 (14)
N1—C1—C6—C5178.83 (11)N1A—C1A—C6A—C5A177.6 (11)
N3—C7—C8—C9178.04 (17)N3A—C7A—C8A—C9A179.9 (15)
N3—C7—C12—N41.36 (14)N3A—C7A—C12A—N4A0.1 (13)
N3—C7—C12—C11177.48 (11)N3A—C7A—C12A—C11A179.9 (11)
N5—C13—C14—C15178.95 (17)N5A—C13A—C14A—C15A177.8 (15)
N5—C13—C18—N60.09 (14)N5A—C13A—C18A—N6A1.8 (12)
N5—C13—C18—C17179.75 (11)N5A—C13A—C18A—C17A178.2 (10)
C1—N1—B1—N20.79 (14)C1A—N1A—B1A—N2A0.4 (12)
C1—N1—B1—N6179.44 (14)C1A—N1A—B1A—N6A177.3 (13)
C1—C2—C3—C40.9 (2)C1A—C2A—C3A—C4A2 (3)
C2—C1—C6—N2179.59 (13)C2A—C1A—C6A—N2A178.1 (12)
C2—C1—C6—C51.5 (2)C2A—C1A—C6A—C5A4 (2)
C2—C3—C4—C50.1 (2)C2A—C3A—C4A—C5A1 (3)
C3—C4—C5—C60.2 (2)C3A—C4A—C5A—C6A1 (2)
C4—C5—C6—N2179.21 (13)C4A—C5A—C6A—N2A179.6 (13)
C4—C5—C6—C10.55 (19)C4A—C5A—C6A—C1A3 (2)
C6—N2—B1—N10.83 (14)C6A—N2A—B1A—N1A0.9 (12)
C6—N2—B1—N6179.35 (11)C6A—N2A—B1A—N6A177.3 (9)
C6—N2—B2—N32.1 (3)C6A—N2A—B2A—N3A2 (2)
C6—N2—B2—N4176.60 (12)C6A—N2A—B2A—N4A177.4 (10)
C6—C1—C2—C31.7 (2)C6A—C1A—C2A—C3A3 (2)
C7—N3—B2—N2178.35 (14)C7A—N3A—B2A—N2A177.2 (12)
C7—N3—B2—N40.47 (14)C7A—N3A—B2A—N4A1.9 (12)
C7—C8—C9—C100.1 (3)C7A—C8A—C9A—C10A2 (3)
C8—C7—C12—N4178.79 (13)C8A—C7A—C12A—N4A179.0 (12)
C8—C7—C12—C112.4 (2)C8A—C7A—C12A—C11A1 (2)
C8—C9—C10—C111.1 (3)C8A—C9A—C10A—C11A2 (3)
C9—C10—C11—C120.5 (2)C9A—C10A—C11A—C12A2 (3)
C10—C11—C12—N4179.74 (14)C10A—C11A—C12A—N4A178.8 (15)
C10—C11—C12—C71.2 (2)C10A—C11A—C12A—C7A2 (2)
C12—N4—B2—N2177.75 (11)C12A—N4A—B2A—N2A178.1 (9)
C12—N4—B2—N31.27 (14)C12A—N4A—B2A—N3A1.9 (11)
C12—N4—B3—N50.4 (2)C12A—N4A—B3A—N5A3 (2)
C12—N4—B3—N6179.55 (12)C12A—N4A—B3A—N6A178.5 (9)
C12—C7—C8—C91.8 (2)C12A—C7A—C8A—C9A1 (2)
C13—N5—B3—N4179.53 (14)C13A—N5A—B3A—N4A179.4 (12)
C13—N5—B3—N61.21 (14)C13A—N5A—B3A—N6A1.8 (12)
C13—C14—C15—C160.6 (3)C13A—C14A—C15A—C16A1 (3)
C14—C13—C18—N6179.70 (14)C14A—C13A—C18A—N6A179.7 (12)
C14—C13—C18—C170.1 (2)C14A—C13A—C18A—C17A0 (2)
C14—C15—C16—C170.0 (3)C14A—C15A—C16A—C17A1 (3)
C15—C16—C17—C180.7 (2)C15A—C16A—C17A—C18A0 (2)
C16—C17—C18—N6179.02 (13)C16A—C17A—C18A—N6A179.9 (13)
C16—C17—C18—C130.78 (19)C16A—C17A—C18A—C13A0.1 (19)
C18—N6—B1—N10.6 (2)C18A—N6A—B1A—N1A0 (2)
C18—N6—B1—N2179.62 (12)C18A—N6A—B1A—N2A177.5 (9)
C18—N6—B3—N4179.36 (11)C18A—N6A—B3A—N4A178.1 (9)
C18—N6—B3—N51.26 (13)C18A—N6A—B3A—N5A2.8 (11)
C18—C13—C14—C150.6 (3)C18A—C13A—C14A—C15A1 (2)
B1—N1—C1—C2179.91 (15)B1A—N1A—C1A—C2A178.6 (13)
B1—N1—C1—C60.45 (14)B1A—N1A—C1A—C6A0.2 (13)
B1—N2—C6—C10.57 (14)B1A—N2A—C6A—C1A1.0 (13)
B1—N2—C6—C5178.21 (13)B1A—N2A—C6A—C5A177.0 (14)
B1—N2—B2—N3178.83 (14)B1A—N2A—B2A—N3A178.8 (12)
B1—N2—B2—N42.45 (18)B1A—N2A—B2A—N4A3.8 (16)
B1—N6—C18—C13178.00 (13)B1A—N6A—C18A—C13A174.6 (11)
B1—N6—C18—C171.8 (2)B1A—N6A—C18A—C17A5.4 (19)
B1—N6—B3—N41.81 (18)B1A—N6A—B3A—N4A4.2 (16)
B1—N6—B3—N5178.81 (11)B1A—N6A—B3A—N5A174.8 (9)
B2—N2—C6—C1178.58 (13)B2A—N2A—C6A—C1A178.0 (11)
B2—N2—C6—C52.6 (2)B2A—N2A—C6A—C5A4 (2)
B2—N2—B1—N1178.43 (11)B2A—N2A—B1A—N1A178.2 (9)
B2—N2—B1—N61.38 (18)B2A—N2A—B1A—N6A3.7 (16)
B2—N3—C7—C8179.63 (15)B2A—N3A—C7A—C8A179.9 (13)
B2—N3—C7—C120.53 (14)B2A—N3A—C7A—C12A1.3 (13)
B2—N4—C12—C71.60 (13)B2A—N4A—C12A—C7A1.1 (12)
B2—N4—C12—C11177.09 (13)B2A—N4A—C12A—C11A178.6 (13)
B2—N4—B3—N5177.03 (13)B2A—N4A—B3A—N5A174.7 (11)
B2—N4—B3—N62.16 (18)B2A—N4A—B3A—N6A4.0 (15)
B3—N4—C12—C7176.07 (12)B3A—N4A—C12A—C7A176.6 (11)
B3—N4—C12—C115.2 (2)B3A—N4A—C12A—C11A4 (2)
B3—N4—B2—N24.25 (18)B3A—N4A—B2A—N2A0.2 (15)
B3—N4—B2—N3176.73 (11)B3A—N4A—B2A—N3A176.1 (9)
B3—N5—C13—C14178.86 (16)B3A—N5A—C13A—C14A178.4 (13)
B3—N5—C13—C180.71 (14)B3A—N5A—C13A—C18A0.0 (13)
B3—N6—C18—C130.83 (14)B3A—N6A—C18A—C13A2.8 (11)
B3—N6—C18—C17178.99 (13)B3A—N6A—C18A—C17A177.2 (12)
B3—N6—B1—N1176.20 (13)B3A—N6A—B1A—N1A177.0 (11)
B3—N6—B1—N23.55 (18)B3A—N6A—B1A—N2A0.5 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O20.89 (1)2.13 (1)2.9817 (14)160 (1)
N5—H5···O10.87 (1)2.09 (1)2.9544 (15)175 (1)
N1A—H1A···O20.88 (2)2.27 (4)3.133 (8)165 (11)
N5A—H5AA···O10.88 (2)2.19 (5)3.026 (8)158 (11)
Comparison of borazine bond lengths (Å) in I and Ia top
IIa
N2—B11.459 (2)N2A—B1A1.433 (12)
N2—B21.429 (2)N2A—B2A1.433 (12)
N4—B21.459 (2)N4A—B2A1.433 (13)
N4—B31.433 (2)N4A—B3A1.429 (12)
N6—B11.428 (2)N6A—B1A1.409 (12)
N6—B31.459 (2)N6A—B3A1.435 (12)
 

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