Crystal structure of bis­(mesit­yl)(pyrrol-1-yl)borane

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.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.037
• wR factor = 0.102
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report

Alert level G
PLAT412_ALERT_2_G Short Intra XH3 .. XHn     H20C     ..H13F     .       2.06 Ang.
                                                      x,y,z  =      1_555 Check
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        398 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        3.4 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         14 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 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
   2 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

---

Computing details

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

Crystal data

C22H26BN	Dx = 1.132 Mg m^−3
Mr = 315.25	Melting point: 411 K
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
a = 11.9157 (2) Å	Cell parameters from 8967 reflections
b = 8.0223 (1) Å	θ = 4.0–79.1°
c = 19.6440 (3) Å	µ = 0.48 mm^−1
β = 99.890 (1)°	T = 120 K
V = 1849.89 (5) Å^3	Plate, colourless
Z = 4	0.24 × 0.22 × 0.07 mm
F(000) = 680

Data collection

XtaLAB Synergy R, DW system, HyPix-Arc 100 diffractometer	3650 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	3305 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.0000 pixels mm^-1	θmax = 80.4°, θmin = 4.1°
ω scans	h = −15→14
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	k = −3→10
Tmin = 0.589, Tmax = 1.000	l = −23→24
12428 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.037	w = 1/[σ^2(Fo^2) + (0.0503P)^2 + 0.5405P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.28 e Å^−3
3650 reflections	Δρmin = −0.19 e Å^−3
240 parameters	Extinction correction: SHELXL2018/3 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0035 (4)
Primary atom site location: dual

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	Occ. (<1)
N1	0.18097 (7)	0.77715 (11)	0.59306 (5)	0.0222 (2)
C1	0.18799 (10)	0.78480 (14)	0.66489 (6)	0.0252 (3)
H1	0.2424 (11)	0.7174 (17)	0.6936 (7)	0.027 (3)*
C2	0.10761 (10)	0.89098 (15)	0.68019 (6)	0.0276 (3)
H2	0.0938 (12)	0.9190 (18)	0.7256 (8)	0.034 (4)*
C3	0.04576 (10)	0.95241 (15)	0.61633 (6)	0.0263 (3)
H3	−0.0173 (12)	1.0297 (19)	0.6110 (7)	0.034 (4)*
C4	0.09209 (9)	0.88346 (14)	0.56483 (6)	0.0243 (2)
H4	0.0713 (11)	0.8919 (17)	0.5145 (7)	0.028 (3)*
C5	0.31151 (9)	0.51849 (13)	0.59337 (5)	0.0203 (2)
C6	0.43044 (9)	0.49950 (13)	0.59754 (5)	0.0204 (2)
C7	0.48525 (9)	0.35880 (14)	0.62875 (5)	0.0220 (2)
H7	0.565353	0.348470	0.631666	0.026*
C8	0.42558 (9)	0.23297 (14)	0.65577 (5)	0.0225 (2)
C9	0.30873 (9)	0.25156 (14)	0.65143 (5)	0.0224 (2)
H9	0.266773	0.165907	0.669121	0.027*
C10	0.25120 (9)	0.39203 (14)	0.62194 (6)	0.0222 (2)
C11	0.50069 (9)	0.63324 (14)	0.57070 (6)	0.0250 (3)
H11A	0.465994	0.662557	0.523314	0.038*
H11B	0.578176	0.591750	0.571152	0.038*
H11C	0.503495	0.732173	0.600204	0.038*
C12	0.48501 (11)	0.08266 (16)	0.69069 (7)	0.0324 (3)
H12A	0.566645	0.089460	0.689114	0.039*	0.459 (14)
H12B	0.473774	0.079013	0.738926	0.039*	0.459 (14)
H12C	0.453368	−0.018501	0.666784	0.039*	0.459 (14)
H12D	0.429213	0.010521	0.707435	0.039*	0.541 (14)
H12E	0.522084	0.020969	0.657624	0.039*	0.541 (14)
H12F	0.542491	0.118483	0.729766	0.039*	0.541 (14)
C13	0.12378 (10)	0.39744 (16)	0.62051 (7)	0.0318 (3)
H13A	0.092836	0.501380	0.598706	0.038*	0.663 (14)
H13B	0.087803	0.302290	0.594031	0.038*	0.663 (14)
H13C	0.108254	0.392161	0.667858	0.038*	0.663 (14)
H13D	0.099760	0.295840	0.641691	0.038*	0.337 (14)
H13E	0.104792	0.494931	0.646366	0.038*	0.337 (14)
H13F	0.084341	0.405060	0.572538	0.038*	0.337 (14)
C14	0.23755 (8)	0.71202 (13)	0.47517 (5)	0.0203 (2)
C15	0.19186 (9)	0.59532 (14)	0.42397 (6)	0.0227 (2)
C16	0.17238 (9)	0.64178 (15)	0.35462 (6)	0.0267 (3)
H16	0.139938	0.562717	0.320900	0.032*
C17	0.19871 (9)	0.79950 (16)	0.33310 (6)	0.0271 (3)
C18	0.24852 (9)	0.91129 (15)	0.38323 (6)	0.0245 (2)
H18	0.269808	1.018547	0.369374	0.029*
C19	0.26830 (9)	0.87098 (14)	0.45335 (6)	0.0217 (2)
C20	0.16008 (10)	0.42065 (15)	0.44205 (7)	0.0310 (3)
H20A	0.226974	0.364914	0.468333	0.046*
H20B	0.133123	0.358118	0.399531	0.046*
H20C	0.099533	0.425544	0.470029	0.046*
C21	0.17317 (13)	0.8475 (2)	0.25774 (7)	0.0422 (3)
H21A	0.197459	0.962807	0.252349	0.051*	0.603 (17)
H21B	0.214358	0.773065	0.231077	0.051*	0.603 (17)
H21C	0.091124	0.837973	0.240847	0.051*	0.603 (17)
H21D	0.137835	0.753090	0.230500	0.051*	0.397 (17)
H21E	0.120936	0.942831	0.251772	0.051*	0.397 (17)
H21F	0.244170	0.877924	0.242002	0.051*	0.397 (17)
C22	0.32315 (11)	1.00106 (15)	0.50381 (6)	0.0291 (3)
H22A	0.263881	1.069083	0.519144	0.044*
H22B	0.372504	1.072516	0.481251	0.044*
H22C	0.368705	0.946066	0.543823	0.044*
B1	0.24540 (10)	0.67087 (15)	0.55475 (6)	0.0209 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0223 (4)	0.0212 (5)	0.0232 (5)	0.0039 (4)	0.0045 (4)	0.0042 (4)
C1	0.0285 (6)	0.0243 (6)	0.0233 (5)	0.0026 (5)	0.0056 (4)	0.0045 (5)
C2	0.0328 (6)	0.0251 (6)	0.0275 (6)	0.0012 (5)	0.0124 (5)	0.0024 (5)
C3	0.0235 (5)	0.0232 (6)	0.0339 (6)	0.0043 (5)	0.0099 (5)	0.0035 (5)
C4	0.0225 (5)	0.0227 (6)	0.0276 (6)	0.0044 (4)	0.0042 (4)	0.0047 (4)
C5	0.0206 (5)	0.0198 (5)	0.0202 (5)	0.0023 (4)	0.0028 (4)	0.0000 (4)
C6	0.0207 (5)	0.0217 (5)	0.0186 (5)	0.0015 (4)	0.0031 (4)	−0.0026 (4)
C7	0.0194 (5)	0.0251 (6)	0.0209 (5)	0.0043 (4)	0.0022 (4)	−0.0022 (4)
C8	0.0267 (5)	0.0211 (5)	0.0190 (5)	0.0054 (4)	0.0018 (4)	−0.0010 (4)
C9	0.0263 (5)	0.0194 (5)	0.0216 (5)	−0.0002 (4)	0.0047 (4)	0.0007 (4)
C10	0.0214 (5)	0.0222 (5)	0.0230 (5)	0.0018 (4)	0.0039 (4)	−0.0003 (4)
C11	0.0207 (5)	0.0253 (6)	0.0292 (6)	0.0003 (4)	0.0046 (4)	0.0016 (5)
C12	0.0328 (6)	0.0283 (6)	0.0355 (7)	0.0095 (5)	0.0040 (5)	0.0069 (5)
C13	0.0224 (5)	0.0272 (6)	0.0467 (7)	0.0020 (5)	0.0087 (5)	0.0082 (5)
C14	0.0166 (5)	0.0205 (5)	0.0235 (5)	0.0045 (4)	0.0028 (4)	0.0007 (4)
C15	0.0164 (5)	0.0242 (6)	0.0270 (6)	0.0034 (4)	0.0020 (4)	−0.0024 (4)
C16	0.0204 (5)	0.0332 (6)	0.0255 (6)	0.0020 (5)	0.0014 (4)	−0.0063 (5)
C17	0.0206 (5)	0.0383 (7)	0.0226 (5)	0.0058 (5)	0.0043 (4)	0.0017 (5)
C18	0.0223 (5)	0.0259 (6)	0.0265 (6)	0.0047 (4)	0.0073 (4)	0.0049 (5)
C19	0.0197 (5)	0.0215 (5)	0.0245 (5)	0.0044 (4)	0.0051 (4)	0.0008 (4)
C20	0.0297 (6)	0.0246 (6)	0.0361 (7)	−0.0027 (5)	−0.0015 (5)	−0.0027 (5)
C21	0.0445 (7)	0.0562 (9)	0.0246 (6)	0.0007 (7)	0.0026 (5)	0.0051 (6)
C22	0.0364 (6)	0.0214 (6)	0.0295 (6)	−0.0021 (5)	0.0057 (5)	0.0009 (5)
B1	0.0177 (5)	0.0188 (6)	0.0256 (6)	−0.0012 (4)	0.0023 (4)	0.0007 (5)

Geometric parameters (Å, º)

N1—C1	1.4005 (14)	C13—H13A	0.9800
N1—C4	1.3981 (14)	C13—H13B	0.9800
N1—B1	1.4425 (15)	C13—H13C	0.9800
C1—H1	0.951 (14)	C13—H13D	0.9800
C1—C2	1.3536 (16)	C13—H13E	0.9800
C2—H2	0.962 (15)	C13—H13F	0.9800
C2—C3	1.4290 (17)	C14—C15	1.4129 (15)
C3—H3	0.966 (15)	C14—C19	1.4135 (15)
C3—C4	1.3514 (17)	C14—B1	1.5848 (16)
C4—H4	0.979 (14)	C15—C16	1.3928 (16)
C5—C6	1.4135 (14)	C15—C20	1.5097 (16)
C5—C10	1.4139 (15)	C16—H16	0.9500
C5—B1	1.5765 (15)	C16—C17	1.3870 (18)
C6—C7	1.3924 (15)	C17—C18	1.3877 (17)
C6—C11	1.5106 (15)	C17—C21	1.5093 (16)
C7—H7	0.9500	C18—H18	0.9500
C7—C8	1.3913 (16)	C18—C19	1.3950 (15)
C8—C9	1.3883 (15)	C19—C22	1.5087 (16)
C8—C12	1.5030 (15)	C20—H20A	0.9800
C9—H9	0.9500	C20—H20B	0.9800
C9—C10	1.3925 (15)	C20—H20C	0.9800
C10—C13	1.5144 (15)	C21—H21A	0.9800
C11—H11A	0.9800	C21—H21B	0.9800
C11—H11B	0.9800	C21—H21C	0.9800
C11—H11C	0.9800	C21—H21D	0.9800
C12—H12A	0.9800	C21—H21E	0.9800
C12—H12B	0.9800	C21—H21F	0.9800
C12—H12C	0.9800	C22—H22A	0.9800
C12—H12D	0.9800	C22—H22B	0.9800
C12—H12E	0.9800	C22—H22C	0.9800
C12—H12F	0.9800
C1—N1—B1	127.34 (9)	C10—C13—H13C	109.5
C4—N1—C1	106.43 (9)	H13A—C13—H13B	109.5
C4—N1—B1	126.05 (9)	H13A—C13—H13C	109.5
N1—C1—H1	119.3 (8)	H13B—C13—H13C	109.5
C2—C1—N1	109.23 (10)	H13D—C13—H13E	109.5
C2—C1—H1	131.5 (8)	H13D—C13—H13F	109.5
C1—C2—H2	126.4 (9)	H13E—C13—H13F	109.5
C1—C2—C3	107.45 (10)	C15—C14—C19	118.05 (10)
C3—C2—H2	126.1 (9)	C15—C14—B1	120.96 (10)
C2—C3—H3	126.2 (8)	C19—C14—B1	120.83 (10)
C4—C3—C2	107.50 (10)	C14—C15—C20	121.94 (10)
C4—C3—H3	126.3 (8)	C16—C15—C14	119.87 (11)
N1—C4—H4	119.1 (8)	C16—C15—C20	118.17 (10)
C3—C4—N1	109.38 (10)	C15—C16—H16	118.9
C3—C4—H4	131.4 (8)	C17—C16—C15	122.27 (11)
C6—C5—C10	118.19 (9)	C17—C16—H16	118.9
C6—C5—B1	121.64 (9)	C16—C17—C18	117.70 (10)
C10—C5—B1	120.09 (9)	C16—C17—C21	120.93 (12)
C5—C6—C11	120.89 (9)	C18—C17—C21	121.38 (12)
C7—C6—C5	120.17 (10)	C17—C18—H18	119.0
C7—C6—C11	118.90 (9)	C17—C18—C19	122.01 (11)
C6—C7—H7	119.2	C19—C18—H18	119.0
C8—C7—C6	121.62 (10)	C14—C19—C22	122.03 (10)
C8—C7—H7	119.2	C18—C19—C14	119.99 (10)
C7—C8—C12	121.64 (10)	C18—C19—C22	117.98 (10)
C9—C8—C7	118.13 (10)	C15—C20—H20A	109.5
C9—C8—C12	120.21 (10)	C15—C20—H20B	109.5
C8—C9—H9	119.0	C15—C20—H20C	109.5
C8—C9—C10	121.96 (10)	H20A—C20—H20B	109.5
C10—C9—H9	119.0	H20A—C20—H20C	109.5
C5—C10—C13	123.26 (10)	H20B—C20—H20C	109.5
C9—C10—C5	119.89 (10)	C17—C21—H21A	109.5
C9—C10—C13	116.82 (10)	C17—C21—H21B	109.5
C6—C11—H11A	109.5	C17—C21—H21C	109.5
C6—C11—H11B	109.5	H21A—C21—H21B	109.5
C6—C11—H11C	109.5	H21A—C21—H21C	109.5
H11A—C11—H11B	109.5	H21B—C21—H21C	109.5
H11A—C11—H11C	109.5	H21D—C21—H21E	109.5
H11B—C11—H11C	109.5	H21D—C21—H21F	109.5
C8—C12—H12A	109.5	H21E—C21—H21F	109.5
C8—C12—H12B	109.5	C19—C22—H22A	109.5
C8—C12—H12C	109.5	C19—C22—H22B	109.5
H12A—C12—H12B	109.5	C19—C22—H22C	109.5
H12A—C12—H12C	109.5	H22A—C22—H22B	109.5
H12B—C12—H12C	109.5	H22A—C22—H22C	109.5
H12D—C12—H12E	109.5	H22B—C22—H22C	109.5
H12D—C12—H12F	109.5	N1—B1—C5	118.30 (10)
H12E—C12—H12F	109.5	N1—B1—C14	116.42 (9)
C10—C13—H13A	109.5	C5—B1—C14	125.18 (9)
C10—C13—H13B	109.5
N1—C1—C2—C3	0.71 (13)	C15—C14—C19—C18	2.85 (15)
C1—N1—C4—C3	−0.47 (13)	C15—C14—C19—C22	−176.89 (10)
C1—N1—B1—C5	14.84 (16)	C15—C14—B1—N1	−117.91 (11)
C1—N1—B1—C14	−168.66 (10)	C15—C14—B1—C5	58.32 (14)
C1—C2—C3—C4	−1.00 (14)	C15—C16—C17—C18	1.52 (16)
C2—C3—C4—N1	0.90 (13)	C15—C16—C17—C21	−178.10 (11)
C4—N1—C1—C2	−0.17 (13)	C16—C17—C18—C19	−2.32 (16)
C4—N1—B1—C5	−159.49 (10)	C17—C18—C19—C14	0.13 (16)
C4—N1—B1—C14	17.01 (16)	C17—C18—C19—C22	179.88 (10)
C5—C6—C7—C8	0.76 (16)	C19—C14—C15—C16	−3.63 (15)
C6—C5—C10—C9	−1.72 (15)	C19—C14—C15—C20	177.97 (10)
C6—C5—C10—C13	−179.75 (10)	C19—C14—B1—N1	57.41 (13)
C6—C5—B1—N1	−122.50 (11)	C19—C14—B1—C5	−126.35 (11)
C6—C5—B1—C14	61.33 (15)	C20—C15—C16—C17	179.94 (10)
C6—C7—C8—C9	−0.56 (16)	C21—C17—C18—C19	177.29 (11)
C6—C7—C8—C12	−178.79 (10)	B1—N1—C1—C2	−175.40 (11)
C7—C8—C9—C10	−0.83 (16)	B1—N1—C4—C3	174.83 (10)
C8—C9—C10—C5	1.98 (16)	B1—C5—C6—C7	−176.49 (10)
C8—C9—C10—C13	−179.85 (10)	B1—C5—C6—C11	5.66 (15)
C10—C5—C6—C7	0.38 (15)	B1—C5—C10—C9	175.21 (10)
C10—C5—C6—C11	−177.47 (10)	B1—C5—C10—C13	−2.83 (16)
C10—C5—B1—N1	60.69 (14)	B1—C14—C15—C16	171.82 (9)
C10—C5—B1—C14	−115.48 (12)	B1—C14—C15—C20	−6.58 (15)
C11—C6—C7—C8	178.65 (10)	B1—C14—C19—C18	−172.60 (9)
C12—C8—C9—C10	177.43 (10)	B1—C14—C19—C22	7.66 (15)
C14—C15—C16—C17	1.48 (16)