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In the crystal structure of the title compound, the dimesitylboron group acts to reduce the delocalization of the nitro­gen atom's lone pair into the pyrrole ring, with increases in the two N—C bond lengths compared to pyrrole itself. The N—B bond is 1.44125 (15) Å long.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989022011768/zv2023sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989022011768/zv2023Isup2.hkl
Contains datablock I

docx

Microsoft Word (DOCX) file https://doi.org/10.1107/S2056989022011768/zv2023sup3.docx
This is NMR data requested by the referee.

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2056989022011768/zv2023Isup4.cml
Supplementary material

CCDC reference: 2166138

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(Pyrrol-1-yl)bis(2,4,6-trimethylphenyl)borane top
Crystal data top
C22H26BNDx = 1.132 Mg m3
Mr = 315.25Melting point: 411 K
Monoclinic, P21/nCu Kα radiation, λ = 1.54184 Å
a = 11.9157 (2) ÅCell parameters from 8967 reflections
b = 8.0223 (1) Åθ = 4.0–79.1°
c = 19.6440 (3) ŵ = 0.48 mm1
β = 99.890 (1)°T = 120 K
V = 1849.89 (5) Å3Plate, colourless
Z = 40.24 × 0.22 × 0.07 mm
F(000) = 680
Data collection top
XtaLAB Synergy R, DW system, HyPix-Arc 100
diffractometer
3650 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source3305 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.021
Detector resolution: 10.0000 pixels mm-1θmax = 80.4°, θmin = 4.1°
ω scansh = 1514
Absorption correction: gaussian
(CrysAlisPro; Rigaku OD, 2022)
k = 310
Tmin = 0.589, Tmax = 1.000l = 2324
12428 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.5405P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.102(Δ/σ)max = 0.001
S = 1.06Δρmax = 0.28 e Å3
3650 reflectionsΔρmin = 0.19 e Å3
240 parametersExtinction correction: SHELXL2018/3 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0035 (4)
Primary atom site location: dual
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*/UeqOcc. (<1)
N10.18097 (7)0.77715 (11)0.59306 (5)0.0222 (2)
C10.18799 (10)0.78480 (14)0.66489 (6)0.0252 (3)
H10.2424 (11)0.7174 (17)0.6936 (7)0.027 (3)*
C20.10761 (10)0.89098 (15)0.68019 (6)0.0276 (3)
H20.0938 (12)0.9190 (18)0.7256 (8)0.034 (4)*
C30.04576 (10)0.95241 (15)0.61633 (6)0.0263 (3)
H30.0173 (12)1.0297 (19)0.6110 (7)0.034 (4)*
C40.09209 (9)0.88346 (14)0.56483 (6)0.0243 (2)
H40.0713 (11)0.8919 (17)0.5145 (7)0.028 (3)*
C50.31151 (9)0.51849 (13)0.59337 (5)0.0203 (2)
C60.43044 (9)0.49950 (13)0.59754 (5)0.0204 (2)
C70.48525 (9)0.35880 (14)0.62875 (5)0.0220 (2)
H70.5653530.3484700.6316660.026*
C80.42558 (9)0.23297 (14)0.65577 (5)0.0225 (2)
C90.30873 (9)0.25156 (14)0.65143 (5)0.0224 (2)
H90.2667730.1659070.6691210.027*
C100.25120 (9)0.39203 (14)0.62194 (6)0.0222 (2)
C110.50069 (9)0.63324 (14)0.57070 (6)0.0250 (3)
H11A0.4659940.6625570.5233140.038*
H11B0.5781760.5917500.5711520.038*
H11C0.5034950.7321730.6002040.038*
C120.48501 (11)0.08266 (16)0.69069 (7)0.0324 (3)
H12A0.5666450.0894600.6891140.039*0.459 (14)
H12B0.4737740.0790130.7389260.039*0.459 (14)
H12C0.4533680.0185010.6667840.039*0.459 (14)
H12D0.4292130.0105210.7074350.039*0.541 (14)
H12E0.5220840.0209690.6576240.039*0.541 (14)
H12F0.5424910.1184830.7297660.039*0.541 (14)
C130.12378 (10)0.39744 (16)0.62051 (7)0.0318 (3)
H13A0.0928360.5013800.5987060.038*0.663 (14)
H13B0.0878030.3022900.5940310.038*0.663 (14)
H13C0.1082540.3921610.6678580.038*0.663 (14)
H13D0.0997600.2958400.6416910.038*0.337 (14)
H13E0.1047920.4949310.6463660.038*0.337 (14)
H13F0.0843410.4050600.5725380.038*0.337 (14)
C140.23755 (8)0.71202 (13)0.47517 (5)0.0203 (2)
C150.19186 (9)0.59532 (14)0.42397 (6)0.0227 (2)
C160.17238 (9)0.64178 (15)0.35462 (6)0.0267 (3)
H160.1399380.5627170.3209000.032*
C170.19871 (9)0.79950 (16)0.33310 (6)0.0271 (3)
C180.24852 (9)0.91129 (15)0.38323 (6)0.0245 (2)
H180.2698081.0185470.3693740.029*
C190.26830 (9)0.87098 (14)0.45335 (6)0.0217 (2)
C200.16008 (10)0.42065 (15)0.44205 (7)0.0310 (3)
H20A0.2269740.3649140.4683330.046*
H20B0.1331230.3581180.3995310.046*
H20C0.0995330.4255440.4700290.046*
C210.17317 (13)0.8475 (2)0.25774 (7)0.0422 (3)
H21A0.1974590.9628070.2523490.051*0.603 (17)
H21B0.2143580.7730650.2310770.051*0.603 (17)
H21C0.0911240.8379730.2408470.051*0.603 (17)
H21D0.1378350.7530900.2305000.051*0.397 (17)
H21E0.1209360.9428310.2517720.051*0.397 (17)
H21F0.2441700.8779240.2420020.051*0.397 (17)
C220.32315 (11)1.00106 (15)0.50381 (6)0.0291 (3)
H22A0.2638811.0690830.5191440.044*
H22B0.3725041.0725160.4812510.044*
H22C0.3687050.9460660.5438230.044*
B10.24540 (10)0.67087 (15)0.55475 (6)0.0209 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0223 (4)0.0212 (5)0.0232 (5)0.0039 (4)0.0045 (4)0.0042 (4)
C10.0285 (6)0.0243 (6)0.0233 (5)0.0026 (5)0.0056 (4)0.0045 (5)
C20.0328 (6)0.0251 (6)0.0275 (6)0.0012 (5)0.0124 (5)0.0024 (5)
C30.0235 (5)0.0232 (6)0.0339 (6)0.0043 (5)0.0099 (5)0.0035 (5)
C40.0225 (5)0.0227 (6)0.0276 (6)0.0044 (4)0.0042 (4)0.0047 (4)
C50.0206 (5)0.0198 (5)0.0202 (5)0.0023 (4)0.0028 (4)0.0000 (4)
C60.0207 (5)0.0217 (5)0.0186 (5)0.0015 (4)0.0031 (4)0.0026 (4)
C70.0194 (5)0.0251 (6)0.0209 (5)0.0043 (4)0.0022 (4)0.0022 (4)
C80.0267 (5)0.0211 (5)0.0190 (5)0.0054 (4)0.0018 (4)0.0010 (4)
C90.0263 (5)0.0194 (5)0.0216 (5)0.0002 (4)0.0047 (4)0.0007 (4)
C100.0214 (5)0.0222 (5)0.0230 (5)0.0018 (4)0.0039 (4)0.0003 (4)
C110.0207 (5)0.0253 (6)0.0292 (6)0.0003 (4)0.0046 (4)0.0016 (5)
C120.0328 (6)0.0283 (6)0.0355 (7)0.0095 (5)0.0040 (5)0.0069 (5)
C130.0224 (5)0.0272 (6)0.0467 (7)0.0020 (5)0.0087 (5)0.0082 (5)
C140.0166 (5)0.0205 (5)0.0235 (5)0.0045 (4)0.0028 (4)0.0007 (4)
C150.0164 (5)0.0242 (6)0.0270 (6)0.0034 (4)0.0020 (4)0.0024 (4)
C160.0204 (5)0.0332 (6)0.0255 (6)0.0020 (5)0.0014 (4)0.0063 (5)
C170.0206 (5)0.0383 (7)0.0226 (5)0.0058 (5)0.0043 (4)0.0017 (5)
C180.0223 (5)0.0259 (6)0.0265 (6)0.0047 (4)0.0073 (4)0.0049 (5)
C190.0197 (5)0.0215 (5)0.0245 (5)0.0044 (4)0.0051 (4)0.0008 (4)
C200.0297 (6)0.0246 (6)0.0361 (7)0.0027 (5)0.0015 (5)0.0027 (5)
C210.0445 (7)0.0562 (9)0.0246 (6)0.0007 (7)0.0026 (5)0.0051 (6)
C220.0364 (6)0.0214 (6)0.0295 (6)0.0021 (5)0.0057 (5)0.0009 (5)
B10.0177 (5)0.0188 (6)0.0256 (6)0.0012 (4)0.0023 (4)0.0007 (5)
Geometric parameters (Å, º) top
N1—C11.4005 (14)C13—H13A0.9800
N1—C41.3981 (14)C13—H13B0.9800
N1—B11.4425 (15)C13—H13C0.9800
C1—H10.951 (14)C13—H13D0.9800
C1—C21.3536 (16)C13—H13E0.9800
C2—H20.962 (15)C13—H13F0.9800
C2—C31.4290 (17)C14—C151.4129 (15)
C3—H30.966 (15)C14—C191.4135 (15)
C3—C41.3514 (17)C14—B11.5848 (16)
C4—H40.979 (14)C15—C161.3928 (16)
C5—C61.4135 (14)C15—C201.5097 (16)
C5—C101.4139 (15)C16—H160.9500
C5—B11.5765 (15)C16—C171.3870 (18)
C6—C71.3924 (15)C17—C181.3877 (17)
C6—C111.5106 (15)C17—C211.5093 (16)
C7—H70.9500C18—H180.9500
C7—C81.3913 (16)C18—C191.3950 (15)
C8—C91.3883 (15)C19—C221.5087 (16)
C8—C121.5030 (15)C20—H20A0.9800
C9—H90.9500C20—H20B0.9800
C9—C101.3925 (15)C20—H20C0.9800
C10—C131.5144 (15)C21—H21A0.9800
C11—H11A0.9800C21—H21B0.9800
C11—H11B0.9800C21—H21C0.9800
C11—H11C0.9800C21—H21D0.9800
C12—H12A0.9800C21—H21E0.9800
C12—H12B0.9800C21—H21F0.9800
C12—H12C0.9800C22—H22A0.9800
C12—H12D0.9800C22—H22B0.9800
C12—H12E0.9800C22—H22C0.9800
C12—H12F0.9800
C1—N1—B1127.34 (9)C10—C13—H13C109.5
C4—N1—C1106.43 (9)H13A—C13—H13B109.5
C4—N1—B1126.05 (9)H13A—C13—H13C109.5
N1—C1—H1119.3 (8)H13B—C13—H13C109.5
C2—C1—N1109.23 (10)H13D—C13—H13E109.5
C2—C1—H1131.5 (8)H13D—C13—H13F109.5
C1—C2—H2126.4 (9)H13E—C13—H13F109.5
C1—C2—C3107.45 (10)C15—C14—C19118.05 (10)
C3—C2—H2126.1 (9)C15—C14—B1120.96 (10)
C2—C3—H3126.2 (8)C19—C14—B1120.83 (10)
C4—C3—C2107.50 (10)C14—C15—C20121.94 (10)
C4—C3—H3126.3 (8)C16—C15—C14119.87 (11)
N1—C4—H4119.1 (8)C16—C15—C20118.17 (10)
C3—C4—N1109.38 (10)C15—C16—H16118.9
C3—C4—H4131.4 (8)C17—C16—C15122.27 (11)
C6—C5—C10118.19 (9)C17—C16—H16118.9
C6—C5—B1121.64 (9)C16—C17—C18117.70 (10)
C10—C5—B1120.09 (9)C16—C17—C21120.93 (12)
C5—C6—C11120.89 (9)C18—C17—C21121.38 (12)
C7—C6—C5120.17 (10)C17—C18—H18119.0
C7—C6—C11118.90 (9)C17—C18—C19122.01 (11)
C6—C7—H7119.2C19—C18—H18119.0
C8—C7—C6121.62 (10)C14—C19—C22122.03 (10)
C8—C7—H7119.2C18—C19—C14119.99 (10)
C7—C8—C12121.64 (10)C18—C19—C22117.98 (10)
C9—C8—C7118.13 (10)C15—C20—H20A109.5
C9—C8—C12120.21 (10)C15—C20—H20B109.5
C8—C9—H9119.0C15—C20—H20C109.5
C8—C9—C10121.96 (10)H20A—C20—H20B109.5
C10—C9—H9119.0H20A—C20—H20C109.5
C5—C10—C13123.26 (10)H20B—C20—H20C109.5
C9—C10—C5119.89 (10)C17—C21—H21A109.5
C9—C10—C13116.82 (10)C17—C21—H21B109.5
C6—C11—H11A109.5C17—C21—H21C109.5
C6—C11—H11B109.5H21A—C21—H21B109.5
C6—C11—H11C109.5H21A—C21—H21C109.5
H11A—C11—H11B109.5H21B—C21—H21C109.5
H11A—C11—H11C109.5H21D—C21—H21E109.5
H11B—C11—H11C109.5H21D—C21—H21F109.5
C8—C12—H12A109.5H21E—C21—H21F109.5
C8—C12—H12B109.5C19—C22—H22A109.5
C8—C12—H12C109.5C19—C22—H22B109.5
H12A—C12—H12B109.5C19—C22—H22C109.5
H12A—C12—H12C109.5H22A—C22—H22B109.5
H12B—C12—H12C109.5H22A—C22—H22C109.5
H12D—C12—H12E109.5H22B—C22—H22C109.5
H12D—C12—H12F109.5N1—B1—C5118.30 (10)
H12E—C12—H12F109.5N1—B1—C14116.42 (9)
C10—C13—H13A109.5C5—B1—C14125.18 (9)
C10—C13—H13B109.5
N1—C1—C2—C30.71 (13)C15—C14—C19—C182.85 (15)
C1—N1—C4—C30.47 (13)C15—C14—C19—C22176.89 (10)
C1—N1—B1—C514.84 (16)C15—C14—B1—N1117.91 (11)
C1—N1—B1—C14168.66 (10)C15—C14—B1—C558.32 (14)
C1—C2—C3—C41.00 (14)C15—C16—C17—C181.52 (16)
C2—C3—C4—N10.90 (13)C15—C16—C17—C21178.10 (11)
C4—N1—C1—C20.17 (13)C16—C17—C18—C192.32 (16)
C4—N1—B1—C5159.49 (10)C17—C18—C19—C140.13 (16)
C4—N1—B1—C1417.01 (16)C17—C18—C19—C22179.88 (10)
C5—C6—C7—C80.76 (16)C19—C14—C15—C163.63 (15)
C6—C5—C10—C91.72 (15)C19—C14—C15—C20177.97 (10)
C6—C5—C10—C13179.75 (10)C19—C14—B1—N157.41 (13)
C6—C5—B1—N1122.50 (11)C19—C14—B1—C5126.35 (11)
C6—C5—B1—C1461.33 (15)C20—C15—C16—C17179.94 (10)
C6—C7—C8—C90.56 (16)C21—C17—C18—C19177.29 (11)
C6—C7—C8—C12178.79 (10)B1—N1—C1—C2175.40 (11)
C7—C8—C9—C100.83 (16)B1—N1—C4—C3174.83 (10)
C8—C9—C10—C51.98 (16)B1—C5—C6—C7176.49 (10)
C8—C9—C10—C13179.85 (10)B1—C5—C6—C115.66 (15)
C10—C5—C6—C70.38 (15)B1—C5—C10—C9175.21 (10)
C10—C5—C6—C11177.47 (10)B1—C5—C10—C132.83 (16)
C10—C5—B1—N160.69 (14)B1—C14—C15—C16171.82 (9)
C10—C5—B1—C14115.48 (12)B1—C14—C15—C206.58 (15)
C11—C6—C7—C8178.65 (10)B1—C14—C19—C18172.60 (9)
C12—C8—C9—C10177.43 (10)B1—C14—C19—C227.66 (15)
C14—C15—C16—C171.48 (16)
Bond lengths (Å) for 1 and related compounds top
1, T = 120 KPyrrole,a T = 103 KPyrrole, calculatedb2,c T = 100 KPyrrole, N—COd
N—B1.4425 (15)1.4094 (9)
N—Cα1.4005 (14) 1.3981 (14)1.365 (2)1.3761.4033 (6)1.395
Cα—Cβ1.3536 (16) 1.3514 (17)1.357 (2)1.3781.3553 (6)1.355
Cβ—Cβ1.4290 (17)1.423 (3)1.4251.4418 (9)1.430
Notes: (a) RUVQII (Goddard et al., 1997); (b) Lee & Boo (1996); (c) CUDZUW01 (Flierler et al., 2009); (d) Averaged data for structures containing C-unsubstituted-N-carbonyl pyrrole fragments measured at T < 150 K [BEFFUQ (Hatano et al., 2016), BOKSUR (Ariyarathna & Tunge, 2014), CIFNIR (O'Brien et al., 2018) and LAQFER (Uraguchi et al., 2017.
 

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