In the course of an attempt to synthesize tetrakis(3,5-dimethylpyridine)dihydridosilicon dibromide, crystals of its acetonitrile disolvate, C28H38N4Si2+·2Br-·2C2H3N, (I), and of 3,5-dimethylpyridinium bromide, C7H10N+·Br-, (II), were obtained in the same reaction flask. They have both been structurally characterized.
Supporting information
CCDC references: 153949; 153950
For both compounds, data collection: SMART (Siemens, 1995); cell refinement: SMART; data reduction: SAINT (Siemens, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
Crystal data top
C28H38N4Si2+·2Br−·2C2H3N | F(000) = 724 |
Mr = 700.64 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.636 (2) Å | Cell parameters from 7291 reflections |
b = 11.237 (2) Å | θ = 1–25° |
c = 16.242 (3) Å | µ = 2.38 mm−1 |
β = 94.49 (1)° | T = 173 K |
V = 1753.3 (6) Å3 | Block, colourless |
Z = 2 | 0.75 × 0.70 × 0.55 mm |
Data collection top
Siemens CCD three-circle diffractometer | 4345 independent reflections |
Radiation source: fine-focus sealed tube | 3390 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
ω scans | θmax = 28.3°, θmin = 2.1° |
Absorption correction: empirical (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.185, Tmax = 0.271 | k = −14→14 |
32839 measured reflections | l = −21→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0451P)2 + 2.4478P] where P = (Fo2 + 2Fc2)/3 |
4345 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.77 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.59423 (4) | 0.11115 (3) | 0.18448 (2) | 0.04740 (14) | |
Si1 | 0.5000 | 0.0000 | 0.5000 | 0.0199 (2) | |
H1 | 0.502 (3) | 0.053 (3) | 0.5730 (19) | 0.029 (8)* | |
N11 | 0.4049 (2) | 0.14032 (19) | 0.44785 (13) | 0.0209 (4) | |
C12 | 0.3822 (3) | 0.2368 (3) | 0.49314 (17) | 0.0261 (6) | |
H12 | 0.4135 | 0.2371 | 0.5501 | 0.031* | |
C13 | 0.3147 (3) | 0.3360 (3) | 0.45965 (18) | 0.0294 (6) | |
C13' | 0.2906 (4) | 0.4435 (3) | 0.5117 (2) | 0.0463 (9) | |
H13A | 0.1910 | 0.4509 | 0.5191 | 0.069* | |
H13B | 0.3227 | 0.5149 | 0.4841 | 0.069* | |
H13C | 0.3424 | 0.4348 | 0.5657 | 0.069* | |
C14 | 0.2698 (3) | 0.3325 (3) | 0.37583 (18) | 0.0296 (6) | |
H14 | 0.2205 | 0.3983 | 0.3513 | 0.036* | |
C15 | 0.2962 (3) | 0.2342 (3) | 0.32808 (17) | 0.0266 (6) | |
C15' | 0.2540 (4) | 0.2312 (3) | 0.23679 (19) | 0.0407 (8) | |
H15A | 0.3354 | 0.2473 | 0.2060 | 0.061* | |
H15B | 0.1828 | 0.2920 | 0.2234 | 0.061* | |
H15C | 0.2163 | 0.1526 | 0.2216 | 0.061* | |
C16 | 0.3652 (3) | 0.1391 (3) | 0.36667 (18) | 0.0261 (6) | |
H16 | 0.3852 | 0.0711 | 0.3349 | 0.031* | |
N21 | 0.6830 (2) | 0.0721 (2) | 0.48468 (14) | 0.0219 (5) | |
C22 | 0.7484 (3) | 0.0463 (3) | 0.41690 (18) | 0.0262 (6) | |
H22 | 0.7042 | −0.0052 | 0.3765 | 0.031* | |
C23 | 0.8784 (3) | 0.0924 (3) | 0.40378 (19) | 0.0315 (6) | |
C23' | 0.9475 (4) | 0.0621 (4) | 0.3263 (2) | 0.0473 (9) | |
H23A | 0.9990 | 0.1315 | 0.3085 | 0.071* | |
H23B | 0.8764 | 0.0397 | 0.2826 | 0.071* | |
H23C | 1.0119 | −0.0045 | 0.3374 | 0.071* | |
C24 | 0.9389 (3) | 0.1684 (3) | 0.4636 (2) | 0.0350 (7) | |
H24 | 1.0283 | 0.2008 | 0.4567 | 0.042* | |
C25 | 0.8719 (3) | 0.1984 (3) | 0.5333 (2) | 0.0333 (7) | |
C25' | 0.9340 (4) | 0.2821 (4) | 0.5985 (2) | 0.0533 (10) | |
H25A | 0.8780 | 0.3549 | 0.5985 | 0.080* | |
H25B | 1.0294 | 0.3022 | 0.5867 | 0.080* | |
H25C | 0.9350 | 0.2438 | 0.6527 | 0.080* | |
C26 | 0.7423 (3) | 0.1470 (3) | 0.54165 (18) | 0.0280 (6) | |
H26 | 0.6943 | 0.1655 | 0.5890 | 0.034* | |
N1 | 0.0894 (4) | 0.5963 (4) | 0.6810 (3) | 0.0832 (14) | |
C2 | 0.2016 (5) | 0.6212 (3) | 0.6741 (3) | 0.0503 (9) | |
C3 | 0.3456 (4) | 0.6544 (3) | 0.6640 (3) | 0.0499 (9) | |
H3A | 0.3541 | 0.6802 | 0.6069 | 0.075* | |
H3B | 0.4063 | 0.5857 | 0.6763 | 0.075* | |
H3C | 0.3731 | 0.7196 | 0.7018 | 0.075* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0436 (2) | 0.0472 (2) | 0.0509 (2) | 0.00162 (16) | 0.00004 (15) | −0.01632 (17) |
Si1 | 0.0192 (5) | 0.0217 (5) | 0.0187 (5) | −0.0016 (4) | −0.0002 (4) | 0.0007 (4) |
N11 | 0.0233 (11) | 0.0206 (11) | 0.0187 (11) | −0.0048 (9) | 0.0007 (8) | 0.0023 (8) |
C12 | 0.0283 (14) | 0.0270 (14) | 0.0230 (13) | −0.0027 (11) | 0.0010 (11) | 0.0023 (11) |
C13 | 0.0322 (15) | 0.0269 (15) | 0.0293 (15) | −0.0006 (12) | 0.0041 (12) | 0.0017 (12) |
C13' | 0.070 (3) | 0.0298 (17) | 0.0395 (19) | 0.0140 (17) | 0.0040 (17) | −0.0016 (14) |
C14 | 0.0253 (14) | 0.0302 (15) | 0.0331 (16) | 0.0018 (12) | 0.0011 (12) | 0.0094 (12) |
C15 | 0.0215 (13) | 0.0327 (15) | 0.0251 (14) | −0.0033 (11) | −0.0013 (11) | 0.0055 (11) |
C15' | 0.0423 (18) | 0.050 (2) | 0.0278 (16) | 0.0066 (16) | −0.0105 (14) | 0.0054 (14) |
C16 | 0.0230 (13) | 0.0282 (14) | 0.0267 (14) | −0.0022 (11) | −0.0002 (11) | −0.0014 (11) |
N21 | 0.0205 (11) | 0.0216 (11) | 0.0232 (11) | −0.0023 (9) | −0.0014 (9) | 0.0030 (9) |
C22 | 0.0260 (14) | 0.0245 (14) | 0.0281 (14) | −0.0020 (11) | 0.0017 (11) | 0.0018 (11) |
C23 | 0.0252 (14) | 0.0337 (16) | 0.0359 (16) | −0.0012 (12) | 0.0050 (12) | 0.0060 (13) |
C23' | 0.0338 (17) | 0.062 (2) | 0.048 (2) | −0.0074 (17) | 0.0170 (15) | −0.0027 (18) |
C24 | 0.0182 (13) | 0.0396 (18) | 0.0464 (19) | −0.0068 (12) | −0.0024 (13) | 0.0089 (14) |
C25 | 0.0258 (15) | 0.0369 (17) | 0.0356 (16) | −0.0067 (12) | −0.0077 (12) | 0.0038 (13) |
C25' | 0.0387 (19) | 0.065 (3) | 0.053 (2) | −0.0210 (18) | −0.0113 (17) | −0.011 (2) |
C26 | 0.0241 (14) | 0.0329 (15) | 0.0262 (14) | −0.0020 (12) | −0.0035 (11) | 0.0028 (12) |
N1 | 0.063 (3) | 0.077 (3) | 0.114 (4) | −0.001 (2) | 0.038 (3) | 0.030 (3) |
C2 | 0.064 (3) | 0.037 (2) | 0.052 (2) | 0.0054 (18) | 0.0178 (19) | 0.0083 (16) |
C3 | 0.053 (2) | 0.0368 (19) | 0.060 (2) | −0.0004 (17) | 0.0039 (18) | −0.0132 (17) |
Geometric parameters (Å, º) top
Si1—H1i | 1.33 (3) | C16—H16 | 0.9500 |
Si1—H1 | 1.33 (3) | N21—C22 | 1.342 (4) |
Si1—N21 | 1.974 (2) | N21—C26 | 1.345 (4) |
Si1—N21i | 1.974 (2) | C22—C23 | 1.388 (4) |
Si1—N11 | 1.980 (2) | C22—H22 | 0.9500 |
Si1—N11i | 1.980 (2) | C23—C24 | 1.387 (5) |
Si1—H1 | 1.33 (3) | C23—C23' | 1.507 (5) |
N11—C12 | 1.338 (4) | C23'—H23A | 0.9800 |
N11—C16 | 1.344 (4) | C23'—H23B | 0.9800 |
C12—C13 | 1.380 (4) | C23'—H23C | 0.9800 |
C12—H12 | 0.9500 | C24—C25 | 1.387 (5) |
C13—C14 | 1.396 (4) | C24—H24 | 0.9500 |
C13—C13' | 1.503 (4) | C25—C26 | 1.392 (4) |
C13'—H13A | 0.9800 | C25—C25' | 1.506 (5) |
C13'—H13B | 0.9800 | C25'—H25A | 0.9800 |
C13'—H13C | 0.9800 | C25'—H25B | 0.9800 |
C14—C15 | 1.385 (4) | C25'—H25C | 0.9800 |
C14—H14 | 0.9500 | C26—H26 | 0.9500 |
C15—C16 | 1.382 (4) | N1—C2 | 1.130 (5) |
C15—C15' | 1.507 (4) | C2—C3 | 1.459 (6) |
C15'—H15A | 0.9800 | C3—H3A | 0.9800 |
C15'—H15B | 0.9800 | C3—H3B | 0.9800 |
C15'—H15C | 0.9800 | C3—H3C | 0.9800 |
| | | |
H1i—Si1—H1 | 180.000 (8) | H15A—C15'—H15B | 109.5 |
H1i—Si1—N21 | 91.2 (14) | C15—C15'—H15C | 109.5 |
H1—Si1—N21 | 88.8 (14) | H15A—C15'—H15C | 109.5 |
H1i—Si1—N21i | 88.8 (14) | H15B—C15'—H15C | 109.5 |
H1—Si1—N21i | 91.2 (14) | N11—C16—C15 | 121.8 (3) |
N21—Si1—N21i | 180.0 | N11—C16—H16 | 119.1 |
H1i—Si1—N11 | 90.3 (14) | C15—C16—H16 | 119.1 |
H1—Si1—N11 | 89.7 (14) | C22—N21—C26 | 119.8 (2) |
N21—Si1—N11 | 90.42 (9) | C22—N21—Si1 | 119.78 (18) |
N21i—Si1—N11 | 89.58 (9) | C26—N21—Si1 | 120.38 (19) |
H1i—Si1—N11i | 89.7 (14) | N21—C22—C23 | 122.2 (3) |
H1—Si1—N11i | 90.3 (14) | N21—C22—H22 | 118.9 |
N21—Si1—N11i | 89.58 (9) | C23—C22—H22 | 118.9 |
N21i—Si1—N11i | 90.42 (9) | C24—C23—C22 | 117.2 (3) |
N11—Si1—N11i | 180.00 (11) | C24—C23—C23' | 122.3 (3) |
H1i—Si1—H1 | 180.000 (8) | C22—C23—C23' | 120.5 (3) |
H1—Si1—H1 | 0 (3) | C23—C23'—H23A | 109.5 |
N21—Si1—H1 | 88.8 (14) | C23—C23'—H23B | 109.5 |
N21i—Si1—H1 | 91.2 (14) | H23A—C23'—H23B | 109.5 |
N11—Si1—H1 | 89.7 (14) | C23—C23'—H23C | 109.5 |
N11i—Si1—H1 | 90.3 (14) | H23A—C23'—H23C | 109.5 |
C12—N11—C16 | 120.1 (2) | H23B—C23'—H23C | 109.5 |
C12—N11—Si1 | 120.02 (18) | C23—C24—C25 | 121.6 (3) |
C16—N11—Si1 | 119.90 (19) | C23—C24—H24 | 119.2 |
N11—C12—C13 | 122.0 (3) | C25—C24—H24 | 119.2 |
N11—C12—H12 | 119.0 | C24—C25—C26 | 117.2 (3) |
C13—C12—H12 | 119.0 | C24—C25—C25' | 122.8 (3) |
C12—C13—C14 | 117.5 (3) | C26—C25—C25' | 120.0 (3) |
C12—C13—C13' | 121.1 (3) | C25—C25'—H25A | 109.5 |
C14—C13—C13' | 121.4 (3) | C25—C25'—H25B | 109.5 |
C13—C13'—H13A | 109.5 | H25A—C25'—H25B | 109.5 |
C13—C13'—H13B | 109.5 | C25—C25'—H25C | 109.5 |
H13A—C13'—H13B | 109.5 | H25A—C25'—H25C | 109.5 |
C13—C13'—H13C | 109.5 | H25B—C25'—H25C | 109.5 |
H13A—C13'—H13C | 109.5 | N21—C26—C25 | 121.9 (3) |
H13B—C13'—H13C | 109.5 | N21—C26—H26 | 119.1 |
C15—C14—C13 | 120.8 (3) | C25—C26—H26 | 119.1 |
C15—C14—H14 | 119.6 | N1—C2—C3 | 179.0 (5) |
C13—C14—H14 | 119.6 | C2—C3—H3A | 109.5 |
C16—C15—C14 | 117.7 (3) | C2—C3—H3B | 109.5 |
C16—C15—C15' | 120.8 (3) | H3A—C3—H3B | 109.5 |
C14—C15—C15' | 121.4 (3) | C2—C3—H3C | 109.5 |
C15—C15'—H15A | 109.5 | H3A—C3—H3C | 109.5 |
C15—C15'—H15B | 109.5 | H3B—C3—H3C | 109.5 |
| | | |
H1i—Si1—N11—C12 | −175.8 (14) | H1i—Si1—N21—C22 | −2.9 (14) |
H1—Si1—N11—C12 | 4.2 (14) | H1—Si1—N21—C22 | 177.1 (14) |
N21—Si1—N11—C12 | −84.6 (2) | N11—Si1—N21—C22 | −93.2 (2) |
N21i—Si1—N11—C12 | 95.4 (2) | N11i—Si1—N21—C22 | 86.8 (2) |
H1i—Si1—N11—C16 | 3.2 (14) | H1i—Si1—N21—C26 | 176.9 (14) |
H1—Si1—N11—C16 | −176.8 (14) | H1—Si1—N21—C26 | −3.1 (14) |
N21—Si1—N11—C16 | 94.3 (2) | N11—Si1—N21—C26 | 86.6 (2) |
N21i—Si1—N11—C16 | −85.7 (2) | N11i—Si1—N21—C26 | −93.4 (2) |
C16—N11—C12—C13 | 2.0 (4) | C26—N21—C22—C23 | 1.6 (4) |
Si1—N11—C12—C13 | −179.1 (2) | Si1—N21—C22—C23 | −178.6 (2) |
N11—C12—C13—C14 | 0.1 (4) | N21—C22—C23—C24 | −0.8 (4) |
N11—C12—C13—C13' | −179.9 (3) | N21—C22—C23—C23' | −179.4 (3) |
C12—C13—C14—C15 | −1.9 (4) | C22—C23—C24—C25 | −0.7 (5) |
C13'—C13—C14—C15 | 178.1 (3) | C23'—C23—C24—C25 | 177.9 (3) |
C13—C14—C15—C16 | 1.5 (4) | C23—C24—C25—C26 | 1.3 (5) |
C13—C14—C15—C15' | −177.3 (3) | C23—C24—C25—C25' | −179.0 (3) |
C12—N11—C16—C15 | −2.3 (4) | C22—N21—C26—C25 | −0.9 (4) |
Si1—N11—C16—C15 | 178.7 (2) | Si1—N21—C26—C25 | 179.3 (2) |
C14—C15—C16—N11 | 0.6 (4) | C24—C25—C26—N21 | −0.5 (4) |
C15'—C15—C16—N11 | 179.4 (3) | C25'—C25—C26—N21 | 179.8 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C15′—H15A···Br1 | 0.98 | 2.97 | 3.705 (4) | 133 |
C25′—H25A···Br1ii | 0.98 | 3.19 | 3.850 (4) | 126 |
C3—H3B···Br1ii | 0.98 | 2.85 | 3.825 (4) | 171 |
C3—H3C···Br1iii | 0.98 | 2.65 | 3.621 (4) | 170 |
Symmetry codes: (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z+1. |
Crystal data top
C7H10N+·Br− | Z = 2 |
Mr = 188.07 | F(000) = 188 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
a = 7.504 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.144 (3) Å | Cell parameters from 5969 reflections |
c = 8.522 (3) Å | θ = 1–25° |
α = 117.80 (1)° | µ = 5.00 mm−1 |
β = 113.43 (1)° | T = 173 K |
γ = 93.01 (1)° | Needle, colourless |
V = 404.1 (2) Å3 | 0.60 × 0.10 × 0.10 mm |
Data collection top
Siemens CCD three-circle diffractometer | 1789 independent reflections |
Radiation source: fine-focus sealed tube | 1531 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
ω scans | θmax = 27.1°, θmin = 2.9° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.153, Tmax = 0.635 | k = −10→10 |
9982 measured reflections | l = −10→10 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0461P)2 + 0.3351P] where P = (Fo2 + 2Fc2)/3 |
1789 reflections | (Δ/σ)max < 0.001 |
88 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.23326 (6) | 0.62640 (6) | 0.86779 (6) | 0.03320 (16) | |
N1 | 0.3894 (5) | 0.3508 (5) | 0.5736 (5) | 0.0301 (7) | |
H1 | 0.346 (8) | 0.424 (8) | 0.661 (8) | 0.049 (14)* | |
C2 | 0.2725 (6) | 0.3105 (6) | 0.3858 (6) | 0.0277 (8) | |
H2 | 0.1549 | 0.3534 | 0.3558 | 0.033* | |
C3 | 0.3238 (6) | 0.2065 (5) | 0.2363 (6) | 0.0261 (8) | |
C31 | 0.2022 (7) | 0.1651 (7) | 0.0277 (6) | 0.0371 (10) | |
H31A | 0.1633 | 0.0254 | −0.0699 | 0.056* | |
H31B | 0.2838 | 0.2359 | 0.0005 | 0.056* | |
H31C | 0.0797 | 0.2067 | 0.0154 | 0.056* | |
C4 | 0.4962 (6) | 0.1453 (6) | 0.2888 (6) | 0.0274 (8) | |
H4 | 0.5333 | 0.0717 | 0.1881 | 0.033* | |
C5 | 0.6166 (6) | 0.1890 (5) | 0.4858 (6) | 0.0281 (8) | |
C51 | 0.8076 (6) | 0.1287 (7) | 0.5429 (7) | 0.0429 (11) | |
H51A | 0.7972 | 0.0142 | 0.4229 | 0.064* | |
H51B | 0.8249 | 0.0974 | 0.6450 | 0.064* | |
H51C | 0.9248 | 0.2353 | 0.5977 | 0.064* | |
C6 | 0.5561 (6) | 0.2946 (6) | 0.6266 (6) | 0.0334 (9) | |
H6 | 0.6333 | 0.3276 | 0.7620 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0309 (2) | 0.0419 (3) | 0.0282 (2) | 0.01640 (18) | 0.01609 (17) | 0.01742 (19) |
N1 | 0.0393 (19) | 0.0230 (17) | 0.0289 (18) | 0.0087 (15) | 0.0215 (16) | 0.0101 (15) |
C2 | 0.0264 (19) | 0.028 (2) | 0.031 (2) | 0.0101 (16) | 0.0156 (17) | 0.0161 (18) |
C3 | 0.0231 (18) | 0.025 (2) | 0.0281 (19) | 0.0040 (15) | 0.0109 (16) | 0.0140 (17) |
C31 | 0.035 (2) | 0.048 (3) | 0.026 (2) | 0.013 (2) | 0.0119 (18) | 0.020 (2) |
C4 | 0.0258 (19) | 0.026 (2) | 0.029 (2) | 0.0070 (16) | 0.0145 (16) | 0.0127 (17) |
C5 | 0.0249 (19) | 0.0218 (19) | 0.030 (2) | 0.0016 (15) | 0.0080 (16) | 0.0127 (17) |
C51 | 0.028 (2) | 0.044 (3) | 0.048 (3) | 0.014 (2) | 0.009 (2) | 0.025 (2) |
C6 | 0.034 (2) | 0.031 (2) | 0.026 (2) | 0.0007 (18) | 0.0078 (17) | 0.0143 (18) |
Geometric parameters (Å, º) top
N1—C6 | 1.335 (5) | C31—H31C | 0.9800 |
N1—C2 | 1.343 (5) | C4—C5 | 1.402 (5) |
N1—H1 | 0.90 (5) | C4—H4 | 0.9500 |
C2—C3 | 1.381 (5) | C5—C6 | 1.377 (6) |
C2—H2 | 0.9500 | C5—C51 | 1.508 (6) |
C3—C4 | 1.392 (5) | C51—H51A | 0.9800 |
C3—C31 | 1.491 (5) | C51—H51B | 0.9800 |
C31—H31A | 0.9800 | C51—H51C | 0.9800 |
C31—H31B | 0.9800 | C6—H6 | 0.9500 |
| | | |
C6—N1—C2 | 123.5 (4) | C3—C4—C5 | 122.0 (4) |
C6—N1—H1 | 124 (3) | C3—C4—H4 | 119.0 |
C2—N1—H1 | 113 (3) | C5—C4—H4 | 119.0 |
N1—C2—C3 | 119.8 (4) | C6—C5—C4 | 117.0 (4) |
N1—C2—H2 | 120.1 | C6—C5—C51 | 121.4 (4) |
C3—C2—H2 | 120.1 | C4—C5—C51 | 121.5 (4) |
C2—C3—C4 | 117.4 (4) | C5—C51—H51A | 109.5 |
C2—C3—C31 | 121.4 (4) | C5—C51—H51B | 109.5 |
C4—C3—C31 | 121.2 (4) | H51A—C51—H51B | 109.5 |
C3—C31—H31A | 109.5 | C5—C51—H51C | 109.5 |
C3—C31—H31B | 109.5 | H51A—C51—H51C | 109.5 |
H31A—C31—H31B | 109.5 | H51B—C51—H51C | 109.5 |
C3—C31—H31C | 109.5 | N1—C6—C5 | 120.3 (4) |
H31A—C31—H31C | 109.5 | N1—C6—H6 | 119.9 |
H31B—C31—H31C | 109.5 | C5—C6—H6 | 119.9 |
| | | |
C6—N1—C2—C3 | −0.3 (6) | C3—C4—C5—C6 | 0.6 (6) |
N1—C2—C3—C4 | 0.9 (5) | C3—C4—C5—C51 | −177.6 (4) |
N1—C2—C3—C31 | −177.7 (4) | C2—N1—C6—C5 | −0.2 (6) |
C2—C3—C4—C5 | −1.0 (6) | C4—C5—C6—N1 | 0.1 (6) |
C31—C3—C4—C5 | 177.6 (4) | C51—C5—C6—N1 | 178.2 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br1 | 0.90 (5) | 2.27 (5) | 3.172 (4) | 175 (4) |
C51—H51C···Br1i | 0.98 | 2.99 | 3.929 (5) | 161 |
C2—H2···Br1ii | 0.95 | 2.84 | 3.749 (4) | 160 |
C31—H31C···Br1ii | 0.98 | 3.05 | 3.980 (5) | 160 |
C6—H6···Br1iii | 0.95 | 2.73 | 3.657 (4) | 166 |
Symmetry codes: (i) x+1, y, z; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+2. |