Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229622010002/zo3028sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229622010002/zo3028Isup2.hkl |
CCDC reference: 2212562
Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015b); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015a); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: X-SEED (Barbour, 2001).
C24H21BBrP | Z = 2 |
Mr = 431.10 | F(000) = 440 |
Triclinic, P1 | Dx = 1.403 Mg m−3 |
a = 9.4920 (6) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.0234 (7) Å | Cell parameters from 9941 reflections |
c = 12.0606 (8) Å | θ = 3.8–72.1° |
α = 81.515 (2)° | µ = 3.51 mm−1 |
β = 74.038 (2)° | T = 100 K |
γ = 67.798 (2)° | Plate, colourless |
V = 1020.21 (12) Å3 | 0.24 × 0.21 × 0.03 mm |
Bruker D8 Venture diffractometer | 3986 independent reflections |
Radiation source: Microsource IuS Incoatec 3.0 | 3904 reflections with I > 2σ(I) |
Double Bounce Multilayer Mirrors monochromator | Rint = 0.022 |
Detector resolution: 7.9 pixels mm-1 | θmax = 72.3°, θmin = 3.8° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | k = −12→7 |
Tmin = 0.644, Tmax = 0.754 | l = −14→14 |
6803 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.025 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.063 | w = 1/[σ2(Fo2) + (0.0215P)2 + 0.9841P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3986 reflections | Δρmax = 0.41 e Å−3 |
250 parameters | Δρmin = −0.53 e Å−3 |
0 restraints |
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 single difference Fourier electron density map 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 boron were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv. The structure was solved by direct methods and refined by full-matrix least-squares analysis onF2using X-Seed (ref) equipped with SHELXT (ref). All non-hydrogen atoms were refined anisotropically by full-matrix least-squares onF2using the SHELXL (ref) program. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.32328 (2) | 0.48490 (2) | 0.10590 (2) | 0.02829 (7) | |
P1 | 0.33317 (4) | 0.25085 (4) | 0.71649 (3) | 0.01089 (9) | |
C1 | 0.27423 (18) | 0.26888 (16) | 0.48269 (13) | 0.0138 (3) | |
C2 | 0.14369 (18) | 0.34670 (17) | 0.43727 (14) | 0.0159 (3) | |
H2 | 0.042212 | 0.357635 | 0.484672 | 0.019* | |
C3 | 0.15653 (19) | 0.40865 (17) | 0.32563 (14) | 0.0184 (3) | |
H3 | 0.065679 | 0.459834 | 0.297054 | 0.022* | |
C4 | 0.3039 (2) | 0.39432 (17) | 0.25703 (14) | 0.0183 (3) | |
C5 | 0.43797 (19) | 0.31845 (17) | 0.29691 (14) | 0.0185 (3) | |
H5 | 0.538792 | 0.308835 | 0.248898 | 0.022* | |
C6 | 0.42157 (18) | 0.25669 (17) | 0.40878 (14) | 0.0170 (3) | |
H6 | 0.513121 | 0.204428 | 0.436253 | 0.020* | |
C7 | 0.24868 (17) | 0.44382 (16) | 0.73670 (13) | 0.0130 (3) | |
C8 | 0.26936 (18) | 0.53691 (17) | 0.63964 (13) | 0.0159 (3) | |
H8 | 0.329205 | 0.498154 | 0.566921 | 0.019* | |
C9 | 0.20268 (19) | 0.68562 (17) | 0.64938 (14) | 0.0180 (3) | |
H9 | 0.217521 | 0.748213 | 0.583525 | 0.022* | |
C10 | 0.11435 (19) | 0.74256 (17) | 0.75545 (15) | 0.0199 (3) | |
H10 | 0.068703 | 0.844141 | 0.762101 | 0.024* | |
C11 | 0.09272 (19) | 0.65123 (18) | 0.85174 (15) | 0.0207 (3) | |
H11 | 0.032144 | 0.690538 | 0.924145 | 0.025* | |
C12 | 0.15934 (18) | 0.50237 (17) | 0.84270 (14) | 0.0169 (3) | |
H12 | 0.143978 | 0.440397 | 0.908890 | 0.020* | |
C13 | 0.54478 (17) | 0.20455 (16) | 0.67799 (12) | 0.0116 (3) | |
C14 | 0.63650 (18) | 0.06484 (16) | 0.64157 (13) | 0.0140 (3) | |
H14 | 0.587565 | 0.001074 | 0.633363 | 0.017* | |
C15 | 0.79873 (18) | 0.01938 (16) | 0.61745 (13) | 0.0149 (3) | |
H15 | 0.860611 | −0.075613 | 0.593161 | 0.018* | |
C16 | 0.87093 (17) | 0.11267 (17) | 0.62878 (13) | 0.0140 (3) | |
H16 | 0.981988 | 0.081366 | 0.612318 | 0.017* | |
C17 | 0.78068 (18) | 0.25123 (17) | 0.66410 (13) | 0.0152 (3) | |
H17 | 0.830186 | 0.314913 | 0.671449 | 0.018* | |
C18 | 0.61755 (18) | 0.29778 (16) | 0.68893 (13) | 0.0141 (3) | |
H18 | 0.556163 | 0.392851 | 0.713263 | 0.017* | |
C19 | 0.29636 (17) | 0.15859 (16) | 0.85681 (13) | 0.0146 (3) | |
C20 | 0.2256 (2) | 0.0560 (2) | 0.87270 (15) | 0.0240 (4) | |
H20 | 0.190504 | 0.038696 | 0.811541 | 0.029* | |
C21 | 0.2063 (2) | −0.0213 (2) | 0.97838 (17) | 0.0290 (4) | |
H21 | 0.160281 | −0.092902 | 0.988478 | 0.035* | |
C22 | 0.2540 (2) | 0.0060 (2) | 1.06842 (15) | 0.0261 (4) | |
H22 | 0.240089 | −0.046403 | 1.140437 | 0.031* | |
C23 | 0.3218 (2) | 0.10963 (19) | 1.05379 (14) | 0.0228 (4) | |
H23 | 0.352238 | 0.129765 | 1.116371 | 0.027* | |
C24 | 0.34567 (18) | 0.18436 (17) | 0.94789 (14) | 0.0174 (3) | |
H24 | 0.395575 | 0.253059 | 0.937423 | 0.021* | |
B1 | 0.2510 (2) | 0.19065 (19) | 0.60936 (16) | 0.0159 (3) | |
H1A | 0.315 (2) | 0.071 (2) | 0.6110 (17) | 0.019* | |
H1B | 0.123 (2) | 0.219 (2) | 0.6589 (17) | 0.019* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.04593 (13) | 0.03054 (12) | 0.01421 (10) | −0.02059 (9) | −0.00767 (8) | 0.00151 (7) |
P1 | 0.01051 (17) | 0.01121 (17) | 0.01213 (18) | −0.00479 (13) | −0.00335 (13) | −0.00028 (13) |
C1 | 0.0168 (7) | 0.0119 (7) | 0.0162 (7) | −0.0067 (6) | −0.0053 (6) | −0.0039 (6) |
C2 | 0.0155 (7) | 0.0151 (7) | 0.0194 (8) | −0.0066 (6) | −0.0048 (6) | −0.0037 (6) |
C3 | 0.0216 (8) | 0.0168 (8) | 0.0214 (8) | −0.0077 (6) | −0.0113 (6) | 0.0000 (6) |
C4 | 0.0295 (9) | 0.0163 (7) | 0.0140 (7) | −0.0120 (7) | −0.0069 (6) | −0.0014 (6) |
C5 | 0.0195 (8) | 0.0189 (8) | 0.0185 (8) | −0.0095 (6) | −0.0007 (6) | −0.0057 (6) |
C6 | 0.0157 (7) | 0.0160 (7) | 0.0204 (8) | −0.0049 (6) | −0.0061 (6) | −0.0034 (6) |
C7 | 0.0106 (6) | 0.0128 (7) | 0.0171 (7) | −0.0039 (5) | −0.0062 (6) | −0.0001 (6) |
C8 | 0.0159 (7) | 0.0184 (8) | 0.0147 (7) | −0.0066 (6) | −0.0050 (6) | −0.0004 (6) |
C9 | 0.0204 (8) | 0.0167 (8) | 0.0200 (8) | −0.0086 (6) | −0.0097 (6) | 0.0046 (6) |
C10 | 0.0188 (8) | 0.0130 (7) | 0.0268 (9) | −0.0014 (6) | −0.0096 (7) | −0.0011 (6) |
C11 | 0.0187 (8) | 0.0189 (8) | 0.0192 (8) | −0.0002 (6) | −0.0035 (6) | −0.0044 (6) |
C12 | 0.0154 (7) | 0.0168 (8) | 0.0162 (8) | −0.0032 (6) | −0.0050 (6) | 0.0014 (6) |
C13 | 0.0119 (7) | 0.0130 (7) | 0.0107 (7) | −0.0050 (5) | −0.0035 (5) | 0.0000 (5) |
C14 | 0.0162 (7) | 0.0127 (7) | 0.0155 (7) | −0.0068 (6) | −0.0048 (6) | −0.0011 (6) |
C15 | 0.0151 (7) | 0.0119 (7) | 0.0157 (7) | −0.0029 (6) | −0.0027 (6) | −0.0022 (6) |
C16 | 0.0117 (7) | 0.0169 (7) | 0.0128 (7) | −0.0051 (6) | −0.0025 (5) | 0.0006 (6) |
C17 | 0.0157 (7) | 0.0162 (7) | 0.0167 (7) | −0.0098 (6) | −0.0034 (6) | −0.0003 (6) |
C18 | 0.0144 (7) | 0.0116 (7) | 0.0163 (7) | −0.0045 (6) | −0.0034 (6) | −0.0020 (6) |
C19 | 0.0120 (7) | 0.0141 (7) | 0.0145 (7) | −0.0023 (6) | −0.0025 (6) | 0.0013 (6) |
C20 | 0.0267 (9) | 0.0271 (9) | 0.0227 (9) | −0.0158 (7) | −0.0071 (7) | 0.0046 (7) |
C21 | 0.0293 (9) | 0.0282 (9) | 0.0294 (10) | −0.0165 (8) | −0.0040 (8) | 0.0105 (8) |
C22 | 0.0224 (8) | 0.0249 (9) | 0.0185 (8) | −0.0016 (7) | 0.0002 (7) | 0.0082 (7) |
C23 | 0.0217 (8) | 0.0217 (8) | 0.0158 (8) | 0.0020 (7) | −0.0044 (6) | −0.0001 (6) |
C24 | 0.0162 (7) | 0.0149 (7) | 0.0171 (8) | −0.0010 (6) | −0.0041 (6) | −0.0010 (6) |
B1 | 0.0170 (8) | 0.0174 (8) | 0.0180 (8) | −0.0091 (7) | −0.0073 (7) | −0.0011 (7) |
Br1—C4 | 1.9062 (16) | C12—H12 | 0.9500 |
P1—C19 | 1.8161 (16) | C13—C18 | 1.394 (2) |
P1—C7 | 1.8175 (15) | C13—C14 | 1.401 (2) |
P1—C13 | 1.8198 (15) | C14—C15 | 1.388 (2) |
P1—B1 | 1.9444 (18) | C14—H14 | 0.9500 |
C1—C2 | 1.400 (2) | C15—C16 | 1.391 (2) |
C1—C6 | 1.408 (2) | C15—H15 | 0.9500 |
C1—B1 | 1.609 (2) | C16—C17 | 1.385 (2) |
C2—C3 | 1.391 (2) | C16—H16 | 0.9500 |
C2—H2 | 0.9500 | C17—C18 | 1.395 (2) |
C3—C4 | 1.382 (2) | C17—H17 | 0.9500 |
C3—H3 | 0.9500 | C18—H18 | 0.9500 |
C4—C5 | 1.388 (2) | C19—C20 | 1.392 (2) |
C5—C6 | 1.392 (2) | C19—C24 | 1.397 (2) |
C5—H5 | 0.9500 | C20—C21 | 1.395 (2) |
C6—H6 | 0.9500 | C20—H20 | 0.9500 |
C7—C12 | 1.395 (2) | C21—C22 | 1.382 (3) |
C7—C8 | 1.403 (2) | C21—H21 | 0.9500 |
C8—C9 | 1.391 (2) | C22—C23 | 1.383 (3) |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—C10 | 1.389 (2) | C23—C24 | 1.389 (2) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C10—C11 | 1.388 (2) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | B1—H1A | 1.12 (2) |
C11—C12 | 1.391 (2) | B1—H1B | 1.14 (2) |
C11—H11 | 0.9500 | ||
C19—P1—C7 | 107.96 (7) | C18—C13—C14 | 119.56 (13) |
C19—P1—C13 | 103.51 (7) | C18—C13—P1 | 123.29 (11) |
C7—P1—C13 | 106.24 (7) | C14—C13—P1 | 117.06 (11) |
C19—P1—B1 | 110.16 (8) | C15—C14—C13 | 120.13 (14) |
C7—P1—B1 | 113.37 (7) | C15—C14—H14 | 119.9 |
C13—P1—B1 | 114.93 (7) | C13—C14—H14 | 119.9 |
C2—C1—C6 | 116.19 (14) | C14—C15—C16 | 120.13 (14) |
C2—C1—B1 | 119.85 (14) | C14—C15—H15 | 119.9 |
C6—C1—B1 | 123.81 (14) | C16—C15—H15 | 119.9 |
C3—C2—C1 | 122.68 (15) | C17—C16—C15 | 119.93 (14) |
C3—C2—H2 | 118.7 | C17—C16—H16 | 120.0 |
C1—C2—H2 | 118.7 | C15—C16—H16 | 120.0 |
C4—C3—C2 | 118.74 (15) | C16—C17—C18 | 120.38 (14) |
C4—C3—H3 | 120.6 | C16—C17—H17 | 119.8 |
C2—C3—H3 | 120.6 | C18—C17—H17 | 119.8 |
C3—C4—C5 | 121.38 (15) | C13—C18—C17 | 119.86 (14) |
C3—C4—Br1 | 119.30 (13) | C13—C18—H18 | 120.1 |
C5—C4—Br1 | 119.30 (13) | C17—C18—H18 | 120.1 |
C4—C5—C6 | 118.60 (15) | C20—C19—C24 | 119.39 (15) |
C4—C5—H5 | 120.7 | C20—C19—P1 | 120.06 (12) |
C6—C5—H5 | 120.7 | C24—C19—P1 | 120.46 (12) |
C5—C6—C1 | 122.40 (15) | C19—C20—C21 | 120.05 (17) |
C5—C6—H6 | 118.8 | C19—C20—H20 | 120.0 |
C1—C6—H6 | 118.8 | C21—C20—H20 | 120.0 |
C12—C7—C8 | 119.17 (14) | C22—C21—C20 | 120.14 (17) |
C12—C7—P1 | 122.87 (12) | C22—C21—H21 | 119.9 |
C8—C7—P1 | 117.90 (12) | C20—C21—H21 | 119.9 |
C9—C8—C7 | 120.32 (14) | C21—C22—C23 | 120.07 (16) |
C9—C8—H8 | 119.8 | C21—C22—H22 | 120.0 |
C7—C8—H8 | 119.8 | C23—C22—H22 | 120.0 |
C10—C9—C8 | 119.95 (15) | C22—C23—C24 | 120.23 (17) |
C10—C9—H9 | 120.0 | C22—C23—H23 | 119.9 |
C8—C9—H9 | 120.0 | C24—C23—H23 | 119.9 |
C11—C10—C9 | 120.08 (15) | C23—C24—C19 | 120.08 (16) |
C11—C10—H10 | 120.0 | C23—C24—H24 | 120.0 |
C9—C10—H10 | 120.0 | C19—C24—H24 | 120.0 |
C10—C11—C12 | 120.29 (15) | C1—B1—P1 | 114.22 (11) |
C10—C11—H11 | 119.9 | C1—B1—H1A | 114.2 (10) |
C12—C11—H11 | 119.9 | P1—B1—H1A | 102.0 (10) |
C11—C12—C7 | 120.19 (15) | C1—B1—H1B | 113.8 (10) |
C11—C12—H12 | 119.9 | P1—B1—H1B | 100.0 (10) |
C7—C12—H12 | 119.9 | H1A—B1—H1B | 111.2 (14) |
C6—C1—C2—C3 | 0.3 (2) | C19—P1—C13—C14 | 75.38 (13) |
B1—C1—C2—C3 | −175.62 (14) | C7—P1—C13—C14 | −171.02 (11) |
C1—C2—C3—C4 | −0.8 (2) | B1—P1—C13—C14 | −44.80 (14) |
C2—C3—C4—C5 | 0.8 (2) | C18—C13—C14—C15 | 0.5 (2) |
C2—C3—C4—Br1 | −177.57 (11) | P1—C13—C14—C15 | −176.17 (12) |
C3—C4—C5—C6 | −0.3 (2) | C13—C14—C15—C16 | −0.3 (2) |
Br1—C4—C5—C6 | 178.03 (11) | C14—C15—C16—C17 | −0.1 (2) |
C4—C5—C6—C1 | −0.2 (2) | C15—C16—C17—C18 | 0.3 (2) |
C2—C1—C6—C5 | 0.2 (2) | C14—C13—C18—C17 | −0.3 (2) |
B1—C1—C6—C5 | 175.92 (14) | P1—C13—C18—C17 | 176.18 (12) |
C19—P1—C7—C12 | −5.66 (15) | C16—C17—C18—C13 | −0.1 (2) |
C13—P1—C7—C12 | −116.17 (13) | C7—P1—C19—C20 | 127.27 (13) |
B1—P1—C7—C12 | 116.67 (13) | C13—P1—C19—C20 | −120.37 (14) |
C19—P1—C7—C8 | 177.19 (11) | B1—P1—C19—C20 | 2.99 (16) |
C13—P1—C7—C8 | 66.69 (13) | C7—P1—C19—C24 | −55.97 (14) |
B1—P1—C7—C8 | −60.48 (14) | C13—P1—C19—C24 | 56.38 (14) |
C12—C7—C8—C9 | 0.5 (2) | B1—P1—C19—C24 | 179.75 (12) |
P1—C7—C8—C9 | 177.80 (12) | C24—C19—C20—C21 | −0.8 (3) |
C7—C8—C9—C10 | −0.4 (2) | P1—C19—C20—C21 | 175.98 (14) |
C8—C9—C10—C11 | 0.1 (2) | C19—C20—C21—C22 | 1.5 (3) |
C9—C10—C11—C12 | 0.1 (2) | C20—C21—C22—C23 | −0.4 (3) |
C10—C11—C12—C7 | 0.1 (2) | C21—C22—C23—C24 | −1.5 (3) |
C8—C7—C12—C11 | −0.4 (2) | C22—C23—C24—C19 | 2.2 (2) |
P1—C7—C12—C11 | −177.52 (12) | C20—C19—C24—C23 | −1.0 (2) |
C19—P1—C13—C18 | −101.16 (13) | P1—C19—C24—C23 | −177.78 (12) |
C7—P1—C13—C18 | 12.44 (15) | C2—C1—B1—P1 | −122.51 (13) |
B1—P1—C13—C18 | 138.67 (13) | C6—C1—B1—P1 | 61.93 (18) |
Cg1 is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···Cg1i | 0.95 | 3.10 | 3.786 | 131 |
C15—H15···Cg1i | 0.95 | 3.31 | 3.890 | 122 |
C17—H17···Cg1ii | 0.95 | 3.28 | 3.947 | 129 |
C18—H18···Cg1ii | 0.95 | 3.49 | 4.047 | 120 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1. |
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