Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014581/wn6045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014581/wn6045Isup2.hkl |
CCDC reference: 175326
Key indicators
- Single-crystal X-ray study
- T = 220 K
- Mean (C-C) = 0.007 Å
- R factor = 0.052
- wR factor = 0.138
- Data-to-parameter ratio = 16.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
RADNW_01 Alert C The radiation wavelength lies outside the expected range for the supplied radiation type. Expected range 1.54175-1.54180 Wavelength given = 1.54056 General Notes
RADNT_01 Extra text has been found in the _diffrn_radiation_type field. Radiation given as CuK\a1 Radiation identified as Cu K\a RADNW_01 The radiation wavelength given implies that Cu Kalpha1 has been used. Please check that this is correct. Wavelength given = 1.54056
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Using Schlenk techniques, THF (10 ml) was added to a mixture of Ni(dppe)2 (40 mg, 0.047 mmol) and N-bromophthalimide (13 mg, 0.058 mmol) and stirred for 5 min. A large excess of hexanes was then addded to the solution, resulting, after 12 h, in the formation of dark-red crystals. The filtrate was removed and the solid dried under N2.
The space group was confirmed by the PLATON program (Spek, 1995). Data reduction was performed using a locally modified version of the NRC-2 program (Ahmed et al., 1973). The structure was solved by direct methods using SHELXS97 (Sheldrick, 1997) and difmap synthesis using SHELXTL (Bruker, 1997) and SHELXL96 (Sheldrick, 1996). H atoms were constrained to ride on the attached atoms; SHELXL96 defaults, C—H = 0.94–0.98 Å. The isotropic displacement parameters, Uiso, were set to values 20% higher than those of the attached atoms. A final verification of possible voids was performed using the VOID routine of the PLATON program (Spek, 1995).
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRC-2 and NRC-2A (Ahmed et al., 1973); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL96 (Sheldrick, 1996); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXL96.
[NiBr2(C26H24P2)]·C4H8O | F(000) = 1392.0 |
Mr = 689.03 | Dx = 1.603 Mg m−3 |
Monoclinic, P21/c | Cu Kα1 radiation, λ = 1.54056 Å |
a = 11.709 (5) Å | Cell parameters from 25 reflections |
b = 14.551 (4) Å | θ = 20.0–21.0° |
c = 17.558 (6) Å | µ = 5.48 mm−1 |
β = 107.38 (3)° | T = 220 K |
V = 2854.9 (17) Å3 | Block, dark red |
Z = 4 | 0.57 × 0.15 × 0.12 mm |
Nonius CAD-4 diffractometer | 4582 reflections with I > 2σ(I) |
Radiation source: normal-focus xray tube | Rint = 0.038 |
Graphite monochromator | θmax = 70.0°, θmin = 4.0° |
ω/2θ scans | h = −14→14 |
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989) | k = −17→17 |
Tmin = 0.234, Tmax = 0.573 | l = −21→21 |
6651 measured reflections | 5 standard reflections every 60 min |
5425 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.1052P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5425 reflections | Δρmax = 1.80 e Å−3 |
326 parameters | Δρmin = −1.12 e Å−3 |
0 restraints | Extinction correction: SHELXL96 (Sheldrick, 1996), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00115 (13) |
[NiBr2(C26H24P2)]·C4H8O | V = 2854.9 (17) Å3 |
Mr = 689.03 | Z = 4 |
Monoclinic, P21/c | Cu Kα1 radiation |
a = 11.709 (5) Å | µ = 5.48 mm−1 |
b = 14.551 (4) Å | T = 220 K |
c = 17.558 (6) Å | 0.57 × 0.15 × 0.12 mm |
β = 107.38 (3)° |
Nonius CAD-4 diffractometer | 4582 reflections with I > 2σ(I) |
Absorption correction: integration (ABSORP in NRCVAX; Gabe et al, 1989) | Rint = 0.038 |
Tmin = 0.234, Tmax = 0.573 | 5 standard reflections every 60 min |
6651 measured reflections | intensity decay: none |
5425 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.02 | Δρmax = 1.80 e Å−3 |
5425 reflections | Δρmin = −1.12 e Å−3 |
326 parameters |
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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
Ni | 0.25326 (5) | 0.29831 (4) | 0.16750 (4) | 0.03025 (18) | |
Br1 | 0.44167 (4) | 0.32094 (3) | 0.15262 (3) | 0.04225 (16) | |
Br2 | 0.16321 (4) | 0.26625 (3) | 0.03209 (2) | 0.04360 (16) | |
P1 | 0.32582 (8) | 0.32090 (6) | 0.29445 (6) | 0.0307 (2) | |
P2 | 0.08503 (8) | 0.26886 (7) | 0.18911 (6) | 0.0340 (2) | |
C1 | 0.2016 (3) | 0.3302 (3) | 0.3369 (2) | 0.0373 (8) | |
H1A | 0.2298 | 0.3197 | 0.3947 | 0.045* | |
H1B | 0.1657 | 0.3915 | 0.3271 | 0.045* | |
C2 | 0.1104 (3) | 0.2573 (3) | 0.2965 (2) | 0.0393 (8) | |
H2A | 0.0355 | 0.2666 | 0.3095 | 0.047* | |
H2B | 0.1410 | 0.1958 | 0.3144 | 0.047* | |
C111 | 0.4244 (3) | 0.4160 (3) | 0.3364 (2) | 0.0354 (8) | |
C112 | 0.3821 (4) | 0.4955 (3) | 0.3634 (3) | 0.0509 (11) | |
H112 | 0.3005 | 0.5006 | 0.3594 | 0.061* | |
C113 | 0.4590 (5) | 0.5667 (3) | 0.3957 (3) | 0.0625 (13) | |
H113 | 0.4296 | 0.6195 | 0.4145 | 0.075* | |
C114 | 0.5788 (5) | 0.5613 (3) | 0.4008 (3) | 0.0585 (13) | |
H114 | 0.6307 | 0.6104 | 0.4221 | 0.070* | |
C115 | 0.6217 (4) | 0.4832 (3) | 0.3743 (3) | 0.0540 (12) | |
H115 | 0.7035 | 0.4790 | 0.3784 | 0.065* | |
C116 | 0.5462 (4) | 0.4109 (3) | 0.3418 (2) | 0.0439 (9) | |
H116 | 0.5765 | 0.3584 | 0.3233 | 0.053* | |
C121 | 0.4058 (3) | 0.2200 (2) | 0.3425 (2) | 0.0320 (7) | |
C122 | 0.4538 (4) | 0.2166 (3) | 0.4255 (3) | 0.0442 (9) | |
H122 | 0.4448 | 0.2669 | 0.4567 | 0.053* | |
C123 | 0.5146 (4) | 0.1390 (3) | 0.4617 (3) | 0.0463 (10) | |
H123 | 0.5467 | 0.1369 | 0.5175 | 0.056* | |
C124 | 0.5283 (4) | 0.0644 (3) | 0.4159 (3) | 0.0442 (9) | |
H124 | 0.5708 | 0.0123 | 0.4408 | 0.053* | |
C125 | 0.4802 (4) | 0.0666 (3) | 0.3349 (3) | 0.0415 (9) | |
H125 | 0.4881 | 0.0155 | 0.3041 | 0.050* | |
C126 | 0.4192 (3) | 0.1446 (2) | 0.2980 (2) | 0.0349 (8) | |
H126 | 0.3869 | 0.1460 | 0.2421 | 0.042* | |
C211 | −0.0267 (3) | 0.3587 (3) | 0.1582 (2) | 0.0387 (8) | |
C212 | −0.1296 (4) | 0.3561 (4) | 0.1827 (3) | 0.0554 (12) | |
H212 | −0.1403 | 0.3085 | 0.2160 | 0.066* | |
C213 | −0.2164 (4) | 0.4242 (4) | 0.1577 (3) | 0.0638 (14) | |
H213 | −0.2860 | 0.4216 | 0.1739 | 0.077* | |
C214 | −0.2018 (4) | 0.4944 (3) | 0.1102 (3) | 0.0563 (12) | |
H214 | −0.2607 | 0.5401 | 0.0937 | 0.068* | |
C215 | −0.1005 (4) | 0.4976 (3) | 0.0867 (3) | 0.0540 (11) | |
H215 | −0.0902 | 0.5462 | 0.0541 | 0.065* | |
C216 | −0.0123 (4) | 0.4301 (3) | 0.1101 (3) | 0.0458 (10) | |
H216 | 0.0566 | 0.4333 | 0.0932 | 0.055* | |
C221 | 0.0158 (4) | 0.1612 (3) | 0.1472 (3) | 0.0431 (9) | |
C222 | 0.0801 (5) | 0.0807 (3) | 0.1687 (3) | 0.0570 (12) | |
H222 | 0.1547 | 0.0819 | 0.2083 | 0.068* | |
C223 | 0.0357 (6) | −0.0018 (3) | 0.1324 (4) | 0.0686 (16) | |
H223 | 0.0801 | −0.0561 | 0.1475 | 0.082* | |
C224 | −0.0725 (6) | −0.0042 (4) | 0.0747 (4) | 0.0749 (19) | |
H224 | −0.1013 | −0.0596 | 0.0484 | 0.090* | |
C225 | −0.1390 (6) | 0.0752 (5) | 0.0554 (3) | 0.0735 (18) | |
H225 | −0.2152 | 0.0725 | 0.0177 | 0.088* | |
C226 | −0.0963 (5) | 0.1589 (4) | 0.0901 (3) | 0.0563 (12) | |
H226 | −0.1419 | 0.2128 | 0.0756 | 0.068* | |
O11 | 0.7740 (4) | 0.2668 (3) | 0.3144 (3) | 0.0755 (11) | |
C12 | 0.7226 (5) | 0.1867 (5) | 0.2718 (4) | 0.0756 (17) | |
H12A | 0.7279 | 0.1887 | 0.2171 | 0.091* | |
H12B | 0.6383 | 0.1811 | 0.2696 | 0.091* | |
C13 | 0.7935 (6) | 0.1077 (5) | 0.3167 (4) | 0.086 (2) | |
H13A | 0.8629 | 0.0945 | 0.2982 | 0.104* | |
H13B | 0.7441 | 0.0523 | 0.3111 | 0.104* | |
C14 | 0.8318 (6) | 0.1418 (5) | 0.4018 (4) | 0.091 (2) | |
H14B | 0.7858 | 0.1114 | 0.4330 | 0.110* | |
H14A | 0.9171 | 0.1301 | 0.4272 | 0.110* | |
C15 | 0.8069 (7) | 0.2426 (5) | 0.3960 (4) | 0.0823 (19) | |
H15B | 0.7418 | 0.2572 | 0.4185 | 0.099* | |
H15A | 0.8783 | 0.2768 | 0.4258 | 0.099* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0251 (3) | 0.0260 (3) | 0.0406 (4) | −0.0004 (2) | 0.0114 (3) | 0.0010 (2) |
Br1 | 0.0351 (2) | 0.0410 (3) | 0.0558 (3) | −0.00752 (16) | 0.02150 (19) | −0.00123 (17) |
Br2 | 0.0391 (3) | 0.0500 (3) | 0.0402 (3) | 0.00253 (17) | 0.00951 (18) | −0.00166 (17) |
P1 | 0.0271 (4) | 0.0251 (4) | 0.0400 (5) | 0.0000 (3) | 0.0104 (4) | −0.0008 (3) |
P2 | 0.0263 (4) | 0.0319 (5) | 0.0444 (5) | −0.0032 (3) | 0.0115 (4) | 0.0006 (4) |
C1 | 0.0346 (19) | 0.0351 (19) | 0.045 (2) | 0.0023 (15) | 0.0159 (16) | −0.0022 (16) |
C2 | 0.0330 (19) | 0.040 (2) | 0.048 (2) | −0.0032 (16) | 0.0164 (17) | 0.0032 (17) |
C111 | 0.0350 (18) | 0.0301 (18) | 0.0383 (19) | 0.0001 (15) | 0.0066 (15) | 0.0028 (14) |
C112 | 0.046 (2) | 0.032 (2) | 0.071 (3) | 0.0010 (18) | 0.012 (2) | −0.0061 (19) |
C113 | 0.072 (3) | 0.033 (2) | 0.075 (3) | −0.007 (2) | 0.010 (3) | −0.012 (2) |
C114 | 0.064 (3) | 0.044 (2) | 0.055 (3) | −0.022 (2) | −0.002 (2) | 0.004 (2) |
C115 | 0.043 (2) | 0.059 (3) | 0.051 (2) | −0.017 (2) | −0.0003 (19) | 0.011 (2) |
C116 | 0.035 (2) | 0.043 (2) | 0.051 (2) | −0.0040 (16) | 0.0078 (17) | 0.0047 (18) |
C121 | 0.0301 (17) | 0.0286 (17) | 0.0388 (19) | −0.0024 (13) | 0.0124 (14) | 0.0009 (14) |
C122 | 0.048 (2) | 0.037 (2) | 0.048 (2) | 0.0065 (18) | 0.0145 (19) | −0.0012 (17) |
C123 | 0.054 (2) | 0.039 (2) | 0.045 (2) | 0.0072 (19) | 0.0128 (19) | 0.0061 (17) |
C124 | 0.043 (2) | 0.033 (2) | 0.057 (2) | 0.0056 (17) | 0.0163 (19) | 0.0111 (17) |
C125 | 0.041 (2) | 0.0261 (18) | 0.061 (3) | 0.0031 (15) | 0.0203 (18) | 0.0023 (17) |
C126 | 0.0324 (17) | 0.0281 (17) | 0.044 (2) | −0.0010 (14) | 0.0114 (15) | 0.0008 (15) |
C211 | 0.0267 (17) | 0.038 (2) | 0.050 (2) | −0.0014 (15) | 0.0105 (15) | −0.0011 (17) |
C212 | 0.036 (2) | 0.057 (3) | 0.079 (3) | 0.003 (2) | 0.025 (2) | 0.009 (2) |
C213 | 0.030 (2) | 0.078 (4) | 0.085 (4) | 0.010 (2) | 0.020 (2) | 0.001 (3) |
C214 | 0.037 (2) | 0.052 (3) | 0.073 (3) | 0.011 (2) | 0.004 (2) | −0.009 (2) |
C215 | 0.050 (2) | 0.040 (2) | 0.071 (3) | 0.008 (2) | 0.016 (2) | 0.003 (2) |
C216 | 0.037 (2) | 0.040 (2) | 0.063 (3) | 0.0011 (17) | 0.0182 (19) | 0.0005 (19) |
C221 | 0.040 (2) | 0.041 (2) | 0.052 (2) | −0.0136 (17) | 0.0185 (18) | −0.0038 (17) |
C222 | 0.053 (3) | 0.036 (2) | 0.085 (4) | −0.008 (2) | 0.027 (2) | −0.001 (2) |
C223 | 0.091 (4) | 0.035 (2) | 0.097 (4) | −0.017 (3) | 0.055 (4) | −0.009 (2) |
C224 | 0.108 (5) | 0.061 (3) | 0.071 (3) | −0.051 (4) | 0.051 (3) | −0.020 (3) |
C225 | 0.079 (4) | 0.084 (4) | 0.055 (3) | −0.049 (3) | 0.017 (3) | −0.014 (3) |
C226 | 0.054 (3) | 0.058 (3) | 0.054 (3) | −0.017 (2) | 0.012 (2) | 0.000 (2) |
O11 | 0.091 (3) | 0.067 (3) | 0.070 (3) | −0.014 (2) | 0.027 (2) | 0.0020 (19) |
C12 | 0.052 (3) | 0.087 (4) | 0.081 (4) | −0.018 (3) | 0.011 (3) | 0.013 (3) |
C13 | 0.067 (4) | 0.067 (4) | 0.111 (5) | 0.004 (3) | 0.006 (4) | −0.002 (4) |
C14 | 0.067 (4) | 0.108 (6) | 0.087 (5) | 0.006 (4) | 0.004 (3) | 0.020 (4) |
C15 | 0.079 (4) | 0.102 (5) | 0.066 (4) | 0.015 (4) | 0.023 (3) | 0.004 (3) |
Ni—P2 | 2.1573 (14) | C126—H126 | 0.9400 |
Ni—P1 | 2.1603 (14) | C211—C216 | 1.381 (6) |
Ni—Br1 | 2.3212 (12) | C211—C212 | 1.396 (6) |
Ni—Br2 | 2.3419 (12) | C212—C213 | 1.392 (7) |
P1—C121 | 1.808 (4) | C212—H212 | 0.9400 |
P1—C111 | 1.811 (4) | C213—C214 | 1.362 (8) |
P1—C1 | 1.827 (4) | C213—H213 | 0.9400 |
P2—C211 | 1.814 (4) | C214—C215 | 1.368 (7) |
P2—C221 | 1.816 (4) | C214—H214 | 0.9400 |
P2—C2 | 1.826 (4) | C215—C216 | 1.394 (6) |
C1—C2 | 1.522 (5) | C215—H215 | 0.9400 |
C1—H1A | 0.9800 | C216—H216 | 0.9400 |
C1—H1B | 0.9800 | C221—C222 | 1.383 (7) |
C2—H2A | 0.9800 | C221—C226 | 1.394 (7) |
C2—H2B | 0.9800 | C222—C223 | 1.385 (7) |
C111—C112 | 1.397 (6) | C222—H222 | 0.9400 |
C111—C116 | 1.403 (5) | C223—C224 | 1.366 (9) |
C112—C113 | 1.379 (6) | C223—H223 | 0.9400 |
C112—H112 | 0.9400 | C224—C225 | 1.378 (9) |
C113—C114 | 1.382 (8) | C224—H224 | 0.9400 |
C113—H113 | 0.9400 | C225—C226 | 1.387 (7) |
C114—C115 | 1.379 (7) | C225—H225 | 0.9400 |
C114—H114 | 0.9400 | C226—H226 | 0.9400 |
C115—C116 | 1.382 (6) | O11—C15 | 1.413 (7) |
C115—H115 | 0.9400 | O11—C12 | 1.419 (7) |
C116—H116 | 0.9400 | C12—C13 | 1.496 (9) |
C121—C126 | 1.383 (5) | C12—H12A | 0.9800 |
C121—C122 | 1.397 (6) | C12—H12B | 0.9800 |
C122—C123 | 1.383 (6) | C13—C14 | 1.511 (10) |
C122—H122 | 0.9400 | C13—H13A | 0.9800 |
C123—C124 | 1.389 (6) | C13—H13B | 0.9800 |
C123—H123 | 0.9400 | C14—C15 | 1.493 (10) |
C124—C125 | 1.364 (6) | C14—H14B | 0.9800 |
C124—H124 | 0.9400 | C14—H14A | 0.9800 |
C125—C126 | 1.394 (5) | C15—H15B | 0.9800 |
C125—H125 | 0.9400 | C15—H15A | 0.9800 |
P2—Ni—P1 | 86.97 (5) | C121—C126—H126 | 119.6 |
P2—Ni—Br1 | 175.13 (4) | C125—C126—H126 | 119.6 |
P1—Ni—Br1 | 90.02 (5) | C216—C211—C212 | 118.9 (4) |
P2—Ni—Br2 | 88.92 (5) | C216—C211—P2 | 121.1 (3) |
P1—Ni—Br2 | 175.46 (4) | C212—C211—P2 | 120.0 (3) |
Br1—Ni—Br2 | 93.95 (4) | C213—C212—C211 | 120.0 (5) |
C121—P1—C111 | 104.58 (17) | C213—C212—H212 | 120.0 |
C121—P1—C1 | 103.52 (18) | C211—C212—H212 | 120.0 |
C111—P1—C1 | 105.42 (18) | C214—C213—C212 | 120.8 (4) |
C121—P1—Ni | 110.30 (13) | C214—C213—H213 | 119.6 |
C111—P1—Ni | 122.85 (13) | C212—C213—H213 | 119.6 |
C1—P1—Ni | 108.47 (14) | C213—C214—C215 | 119.3 (4) |
C211—P2—C221 | 107.8 (2) | C213—C214—H214 | 120.3 |
C211—P2—C2 | 104.83 (19) | C215—C214—H214 | 120.3 |
C221—P2—C2 | 104.73 (19) | C214—C215—C216 | 121.3 (5) |
C211—P2—Ni | 114.77 (14) | C214—C215—H215 | 119.4 |
C221—P2—Ni | 114.88 (14) | C216—C215—H215 | 119.4 |
C2—P2—Ni | 108.92 (13) | C211—C216—C215 | 119.7 (4) |
C2—C1—P1 | 106.9 (3) | C211—C216—H216 | 120.2 |
C2—C1—H1A | 110.3 | C215—C216—H216 | 120.2 |
P1—C1—H1A | 110.3 | C222—C221—C226 | 119.7 (4) |
C2—C1—H1B | 110.3 | C222—C221—P2 | 118.6 (3) |
P1—C1—H1B | 110.3 | C226—C221—P2 | 121.5 (4) |
H1A—C1—H1B | 108.6 | C221—C222—C223 | 120.6 (5) |
C1—C2—P2 | 107.0 (3) | C221—C222—H222 | 119.7 |
C1—C2—H2A | 110.3 | C223—C222—H222 | 119.7 |
P2—C2—H2A | 110.3 | C224—C223—C222 | 120.1 (6) |
C1—C2—H2B | 110.3 | C224—C223—H223 | 119.9 |
P2—C2—H2B | 110.3 | C222—C223—H223 | 119.9 |
H2A—C2—H2B | 108.6 | C223—C224—C225 | 119.5 (5) |
C112—C111—C116 | 118.5 (4) | C223—C224—H224 | 120.3 |
C112—C111—P1 | 121.5 (3) | C225—C224—H224 | 120.3 |
C116—C111—P1 | 119.9 (3) | C224—C225—C226 | 121.7 (5) |
C113—C112—C111 | 120.6 (4) | C224—C225—H225 | 119.2 |
C113—C112—H112 | 119.7 | C226—C225—H225 | 119.2 |
C111—C112—H112 | 119.7 | C225—C226—C221 | 118.4 (5) |
C112—C113—C114 | 120.6 (5) | C225—C226—H226 | 120.8 |
C112—C113—H113 | 119.7 | C221—C226—H226 | 120.8 |
C114—C113—H113 | 119.7 | C15—O11—C12 | 105.9 (5) |
C115—C114—C113 | 119.4 (4) | O11—C12—C13 | 105.8 (5) |
C115—C114—H114 | 120.3 | O11—C12—H12A | 110.6 |
C113—C114—H114 | 120.3 | C13—C12—H12A | 110.6 |
C114—C115—C116 | 120.9 (4) | O11—C12—H12B | 110.6 |
C114—C115—H115 | 119.5 | C13—C12—H12B | 110.6 |
C116—C115—H115 | 119.5 | H12A—C12—H12B | 108.7 |
C115—C116—C111 | 120.0 (4) | C12—C13—C14 | 102.9 (6) |
C115—C116—H116 | 120.0 | C12—C13—H13A | 111.2 |
C111—C116—H116 | 120.0 | C14—C13—H13A | 111.2 |
C126—C121—C122 | 118.8 (4) | C12—C13—H13B | 111.2 |
C126—C121—P1 | 120.7 (3) | C14—C13—H13B | 111.2 |
C122—C121—P1 | 120.4 (3) | H13A—C13—H13B | 109.1 |
C123—C122—C121 | 120.0 (4) | C15—C14—C13 | 105.1 (6) |
C123—C122—H122 | 120.0 | C15—C14—H14B | 110.7 |
C121—C122—H122 | 120.0 | C13—C14—H14B | 110.7 |
C122—C123—C124 | 120.3 (4) | C15—C14—H14A | 110.7 |
C122—C123—H123 | 119.9 | C13—C14—H14A | 110.7 |
C124—C123—H123 | 119.9 | H14B—C14—H14A | 108.8 |
C125—C124—C123 | 120.1 (4) | O11—C15—C14 | 107.6 (6) |
C125—C124—H124 | 119.9 | O11—C15—H15B | 110.2 |
C123—C124—H124 | 119.9 | C14—C15—H15B | 110.2 |
C124—C125—C126 | 119.9 (4) | O11—C15—H15A | 110.2 |
C124—C125—H125 | 120.0 | C14—C15—H15A | 110.2 |
C126—C125—H125 | 120.0 | H15B—C15—H15A | 108.5 |
C121—C126—C125 | 120.8 (4) | ||
P2—Ni—P1—C121 | 99.08 (13) | P1—C121—C122—C123 | 179.9 (3) |
Br1—Ni—P1—C121 | −77.09 (13) | C121—C122—C123—C124 | 0.0 (7) |
P2—Ni—P1—C111 | −136.98 (15) | C122—C123—C124—C125 | −1.0 (7) |
Br1—Ni—P1—C111 | 46.85 (15) | C123—C124—C125—C126 | 1.3 (6) |
P2—Ni—P1—C1 | −13.65 (14) | C122—C121—C126—C125 | −0.4 (6) |
Br1—Ni—P1—C1 | 170.18 (13) | P1—C121—C126—C125 | −179.6 (3) |
P1—Ni—P2—C211 | 105.85 (15) | C124—C125—C126—C121 | −0.6 (6) |
Br2—Ni—P2—C211 | −76.08 (15) | C221—P2—C211—C216 | −116.6 (4) |
P1—Ni—P2—C221 | −128.35 (17) | C2—P2—C211—C216 | 132.2 (4) |
Br2—Ni—P2—C221 | 49.71 (17) | Ni—P2—C211—C216 | 12.8 (4) |
P1—Ni—P2—C2 | −11.28 (15) | C221—P2—C211—C212 | 63.1 (4) |
Br2—Ni—P2—C2 | 166.79 (14) | C2—P2—C211—C212 | −48.1 (4) |
C121—P1—C1—C2 | −76.2 (3) | Ni—P2—C211—C212 | −167.5 (3) |
C111—P1—C1—C2 | 174.3 (3) | C216—C211—C212—C213 | 0.9 (7) |
Ni—P1—C1—C2 | 41.0 (3) | P2—C211—C212—C213 | −178.8 (4) |
P1—C1—C2—P2 | −49.3 (3) | C211—C212—C213—C214 | −0.8 (8) |
C211—P2—C2—C1 | −84.1 (3) | C212—C213—C214—C215 | 0.2 (8) |
C221—P2—C2—C1 | 162.5 (3) | C213—C214—C215—C216 | 0.3 (8) |
Ni—P2—C2—C1 | 39.1 (3) | C212—C211—C216—C215 | −0.4 (7) |
C121—P1—C111—C112 | −133.7 (4) | P2—C211—C216—C215 | 179.3 (4) |
C1—P1—C111—C112 | −24.9 (4) | C214—C215—C216—C211 | −0.2 (7) |
Ni—P1—C111—C112 | 99.8 (4) | C211—P2—C221—C222 | −173.9 (4) |
C121—P1—C111—C116 | 46.8 (4) | C2—P2—C221—C222 | −62.7 (4) |
C1—P1—C111—C116 | 155.6 (3) | Ni—P2—C221—C222 | 56.7 (4) |
Ni—P1—C111—C116 | −79.7 (3) | C211—P2—C221—C226 | 10.6 (5) |
C116—C111—C112—C113 | −1.1 (7) | C2—P2—C221—C226 | 121.8 (4) |
P1—C111—C112—C113 | 179.5 (4) | Ni—P2—C221—C226 | −118.7 (4) |
C111—C112—C113—C114 | 1.1 (8) | C226—C221—C222—C223 | 1.9 (7) |
C112—C113—C114—C115 | −1.0 (8) | P2—C221—C222—C223 | −173.7 (4) |
C113—C114—C115—C116 | 0.9 (7) | C221—C222—C223—C224 | 0.1 (8) |
C114—C115—C116—C111 | −0.9 (7) | C222—C223—C224—C225 | −2.6 (8) |
C112—C111—C116—C115 | 0.9 (6) | C223—C224—C225—C226 | 3.3 (8) |
P1—C111—C116—C115 | −179.6 (3) | C224—C225—C226—C221 | −1.4 (8) |
C111—P1—C121—C126 | −130.5 (3) | C222—C221—C226—C225 | −1.2 (7) |
C1—P1—C121—C126 | 119.3 (3) | P2—C221—C226—C225 | 174.2 (4) |
Ni—P1—C121—C126 | 3.4 (3) | C15—O11—C12—C13 | −36.8 (7) |
C111—P1—C121—C122 | 50.3 (4) | O11—C12—C13—C14 | 30.7 (7) |
C1—P1—C121—C122 | −59.9 (4) | C12—C13—C14—C15 | −13.6 (7) |
Ni—P1—C121—C122 | −175.8 (3) | C12—O11—C15—C14 | 27.8 (7) |
C126—C121—C122—C123 | 0.6 (6) | C13—C14—C15—O11 | −7.9 (8) |
Experimental details
Crystal data | |
Chemical formula | [NiBr2(C26H24P2)]·C4H8O |
Mr | 689.03 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 220 |
a, b, c (Å) | 11.709 (5), 14.551 (4), 17.558 (6) |
β (°) | 107.38 (3) |
V (Å3) | 2854.9 (17) |
Z | 4 |
Radiation type | Cu Kα1 |
µ (mm−1) | 5.48 |
Crystal size (mm) | 0.57 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Nonius CAD-4 diffractometer |
Absorption correction | Integration (ABSORP in NRCVAX; Gabe et al, 1989) |
Tmin, Tmax | 0.234, 0.573 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6651, 5425, 4582 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.610 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.138, 1.02 |
No. of reflections | 5425 |
No. of parameters | 326 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 1.80, −1.12 |
Computer programs: CAD-4 Software (Enraf-Nonius, 1989), CAD-4 Software, NRC-2 and NRC-2A (Ahmed et al., 1973), SHELXS97 (Sheldrick, 1997), SHELXL96 (Sheldrick, 1996), SHELXTL (Bruker, 1997), SHELXL96.
Ni—P2 | 2.1573 (14) | Ni—Br1 | 2.3212 (12) |
Ni—P1 | 2.1603 (14) | Ni—Br2 | 2.3419 (12) |
P2—Ni—P1 | 86.97 (5) | P2—Ni—Br2 | 88.92 (5) |
P2—Ni—Br1 | 175.13 (4) | P1—Ni—Br2 | 175.46 (4) |
P1—Ni—Br1 | 90.02 (5) | Br1—Ni—Br2 | 93.95 (4) |
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In the course of our studies, the formation of Ni(dppe)Br2 was observed as a by-product for the reaction of Ni(dppe)2 with N-bromophthalimide. Even though this compound is well known as a good starting product, only the CH2Cl2 adduct has been previously characterized using X-ray crystallography (Rahn et al., 1989). The structure of the THF adduct, (I) (Fig. 1), is isostructural with the one previously reported for the CH2Cl2 analogue, having a slightly larger volume (about 20 Å3), presumably because of the larger volume of THF compared to CH2Cl2. The THF adduct adopts a pseudo-square planar geometry with a P—Ni—P bite angle of 89.97 (5)° and an angle of 93.93 (4)° between the Br atoms. We note that the Ni—P bond lengths [2.1573 (14) and 2.1603 (14) Å] are also slightly longer in the THF adduct than the corresponding distances in the CH2Cl2 adduct [2.141 (1) and 2.156 (1) Å], but both Ni—Br bonds are very similar. In this structure, there is a stacking interaction between the THF ring and the C121–C126 phenyl ring, as shown in Fig. 2.