Buy article online - an online subscription or single-article purchase is required to access this article.
metal-organic compounds
The Ni atom in the title compound, [Ni(C13H15BrNO)2], is chelated through the O and N atoms of the ligands in a distorted square-planar geometry. The Ni atom lies on a twofold rotation axis. Adjacent molecules are linked by BrBr interactions into a chain.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805000930/kp6032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805000930/kp6032Isup2.hkl |
CCDC reference: 263559
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.005 Å
- R factor = 0.033
- wR factor = 0.091
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - O1 .. 5.39 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Ni1 - N1 .. 5.24 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
Crystal data top
[Ni(C13H15BrNO)2] | F(000) = 1256 |
Mr = 621.05 | Dx = 1.606 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4617 reflections |
a = 17.2129 (9) Å | θ = 2.4–26.7° |
b = 13.5010 (7) Å | µ = 3.89 mm−1 |
c = 11.3932 (6) Å | T = 295 K |
β = 103.979 (1)° | Block, green |
V = 2569.3 (2) Å3 | 0.22 × 0.12 × 0.08 mm |
Z = 4 |
Data collection top
Bruker APEX area-detector diffractometer | 2952 independent reflections |
Radiation source: fine-focus sealed tube | 2397 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −22→22 |
Tmin = 0.469, Tmax = 0.731 | k = −17→17 |
14551 measured reflections | l = −14→14 |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0409P)2 + 3.2642P] where P = (Fo2 + 2Fc2)/3 |
2952 reflections | (Δ/σ)max = 0.001 |
150 parameters | Δρmax = 0.53 e Å−3 |
0 restraints | Δρmin = −0.49 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Br1 | 0.39256 (2) | 0.10822 (3) | 0.69025 (3) | 0.0690 (1) | |
Ni1 | 0.0000 | 0.13160 (3) | 0.2500 | 0.0379 (1) | |
O1 | 0.1088 (1) | 0.0980 (2) | 0.2629 (2) | 0.0517 (5) | |
N1 | 0.0177 (1) | 0.1640 (2) | 0.4231 (2) | 0.0433 (5) | |
C1 | 0.1690 (2) | 0.1038 (2) | 0.3572 (2) | 0.0429 (6) | |
C2 | 0.2461 (2) | 0.0794 (2) | 0.3445 (3) | 0.0500 (6) | |
C3 | 0.3119 (2) | 0.0813 (2) | 0.4417 (3) | 0.0538 (7) | |
C4 | 0.3025 (2) | 0.1074 (2) | 0.5551 (3) | 0.0485 (6) | |
C5 | 0.2290 (2) | 0.1329 (2) | 0.5715 (2) | 0.0485 (6) | |
C6 | 0.1610 (2) | 0.1320 (2) | 0.4735 (2) | 0.0420 (5) | |
C7 | 0.0863 (2) | 0.1607 (2) | 0.4980 (2) | 0.0465 (6) | |
C8 | −0.0518 (2) | 0.1960 (2) | 0.4704 (2) | 0.0481 (6) | |
C9 | −0.0431 (2) | 0.2995 (2) | 0.5226 (3) | 0.0589 (7) | |
C10 | −0.1197 (2) | 0.3294 (3) | 0.5583 (3) | 0.0696 (9) | |
C11 | −0.1411 (2) | 0.2564 (3) | 0.6447 (3) | 0.0726 (9) | |
C12 | −0.1451 (2) | 0.1526 (3) | 0.5982 (4) | 0.086 (1) | |
C13 | −0.0697 (2) | 0.1225 (2) | 0.5600 (4) | 0.071 (1) | |
H2 | 0.2528 | 0.0616 | 0.2687 | 0.060* | |
H3 | 0.3623 | 0.0651 | 0.4312 | 0.065* | |
H5 | 0.2238 | 0.1510 | 0.6480 | 0.058* | |
H7 | 0.0878 | 0.1789 | 0.5773 | 0.056* | |
H8 | −0.0985 | 0.1969 | 0.4014 | 0.058* | |
H9a | −0.0324 | 0.3457 | 0.4631 | 0.071* | |
H9b | 0.0018 | 0.3017 | 0.5930 | 0.071* | |
H10a | −0.1126 | 0.3944 | 0.5957 | 0.084* | |
H10b | −0.1633 | 0.3336 | 0.4863 | 0.084* | |
H11a | −0.1015 | 0.2600 | 0.7213 | 0.087* | |
H11b | −0.1926 | 0.2743 | 0.6592 | 0.087* | |
H12a | −0.1908 | 0.1464 | 0.5295 | 0.103* | |
H12b | −0.1532 | 0.1078 | 0.6607 | 0.103* | |
H13a | −0.0249 | 0.1196 | 0.6305 | 0.085* | |
H13b | −0.0769 | 0.0571 | 0.5236 | 0.085* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0399 (2) | 0.0896 (3) | 0.0678 (2) | −0.0035 (1) | −0.0061 (1) | 0.0001 (2) |
Ni1 | 0.0314 (2) | 0.0518 (3) | 0.0296 (2) | 0.000 | 0.0057 (2) | 0.000 |
O1 | 0.041 (1) | 0.076 (1) | 0.037 (1) | 0.011 (1) | 0.007 (1) | −0.001 (1) |
N1 | 0.036 (1) | 0.058 (1) | 0.036 (1) | 0.003 (1) | 0.008 (1) | −0.002 (1) |
C1 | 0.039 (1) | 0.049 (1) | 0.041 (1) | 0.003 (1) | 0.010 (1) | 0.005 (1) |
C2 | 0.044 (1) | 0.061 (2) | 0.048 (1) | 0.003 (1) | 0.016 (1) | 0.004 (1) |
C3 | 0.035 (1) | 0.059 (2) | 0.068 (2) | 0.002 (1) | 0.014 (1) | 0.007 (1) |
C4 | 0.033 (1) | 0.057 (2) | 0.051 (2) | −0.003 (1) | 0.001 (1) | 0.005 (1) |
C5 | 0.040 (1) | 0.059 (2) | 0.044 (1) | −0.002 (1) | 0.006 (1) | −0.002 (1) |
C6 | 0.036 (1) | 0.048 (1) | 0.042 (1) | 0.002 (1) | 0.009 (1) | 0.002 (1) |
C7 | 0.042 (1) | 0.062 (2) | 0.035 (1) | 0.004 (1) | 0.009 (1) | −0.005 (1) |
C8 | 0.035 (1) | 0.067 (2) | 0.041 (1) | 0.003 (1) | 0.008 (1) | −0.007 (2) |
C9 | 0.058 (2) | 0.057 (2) | 0.064 (2) | 0.011 (1) | 0.020 (1) | 0.004 (1) |
C10 | 0.072 (2) | 0.066 (2) | 0.075 (2) | 0.021 (2) | 0.0259 (2) | 0.001 (2) |
C11 | 0.072 (2) | 0.089 (3) | 0.065 (2) | 0.020 (2) | 0.033 (2) | 0.002 (2) |
C12 | 0.074 (2) | 0.078 (2) | 0.126 (3) | −0.001 (2) | 0.063 (2) | 0.004 (2) |
C13 | 0.068 (2) | 0.054 (2) | 0.106 (3) | 0.000 (2) | 0.051 (2) | −0.003 (2) |
Geometric parameters (Å, º) top
Br1—C4 | 1.902 (3) | C10—C11 | 1.500 (5) |
Ni1—O1 | 1.897 (2) | C11—C12 | 1.494 (5) |
Ni1—O1i | 1.897 (2) | C12—C13 | 1.521 (4) |
Ni1—N1 | 1.971 (2) | C2—H2 | 0.93 |
Ni1—N1i | 1.971 (2) | C3—H3 | 0.93 |
O1—C1 | 1.302 (3) | C5—H5 | 0.93 |
N1—C7 | 1.279 (3) | C7—H7 | 0.93 |
N1—C8 | 1.490 (3) | C8—H8 | 0.98 |
C1—C2 | 1.409 (4) | C9—H9a | 0.97 |
C1—C6 | 1.416 (4) | C9—H9b | 0.97 |
C2—C3 | 1.380 (4) | C10—H10a | 0.97 |
C3—C4 | 1.386 (4) | C10—H10b | 0.97 |
C4—C5 | 1.367 (4) | C11—H11a | 0.97 |
C5—C6 | 1.410 (4) | C11—H11b | 0.97 |
C6—C7 | 1.434 (4) | C12—H12a | 0.97 |
C8—C13 | 1.509 (4) | C12—H12b | 0.97 |
C8—C9 | 1.511 (4) | C13—H13a | 0.97 |
C9—C10 | 1.527 (4) | C13—H13b | 0.97 |
O1—Ni1—O1i | 152.3 (1) | C4—C3—H3 | 120.2 |
O1—Ni1—N1 | 93.7 (1) | C4—C5—H5 | 119.7 |
O1—Ni1—N1i | 92.4 (1) | C6—C5—H5 | 119.7 |
O1i—Ni1—N1 | 92.4 (1) | N1—C7—H7 | 116.4 |
O1i—Ni1—N1i | 93.7 (1) | C6—C7—H7 | 116.4 |
N1—Ni1—N1i | 154.4 (1) | N1—C8—H8 | 106.8 |
C1—O1—Ni1 | 128.6 (2) | C13—C8—H8 | 106.8 |
C7—N1—C8 | 117.4 (2) | C9—C8—H8 | 106.8 |
C7—N1—Ni1 | 123.7 (2) | C8—C9—H9a | 109.7 |
C8—N1—Ni1 | 118.9 (2) | C10—C9—H9a | 109.7 |
O1—C1—C2 | 118.9 (2) | C8—C9—H9b | 109.7 |
O1—C1—C6 | 123.4 (2) | C10—C9—H9b | 109.7 |
C2—C1—C6 | 117.7 (2) | H9a—C9—H9b | 108.2 |
C3—C2—C1 | 121.6 (3) | C11—C10—H10a | 109.3 |
C2—C3—C4 | 119.7 (3) | C9—C10—H10a | 109.3 |
C5—C4—C3 | 120.8 (3) | C11—C10—H10b | 109.3 |
C5—C4—Br1 | 119.2 (2) | C9—C10—H10b | 109.3 |
C3—C4—Br1 | 120.0 (2) | H10a—C10—H10b | 108.0 |
C4—C5—C6 | 120.6 (3) | C12—C11—H11a | 109.1 |
C5—C6—C1 | 119.6 (2) | C10—C11—H11a | 109.1 |
C5—C6—C7 | 117.1 (2) | C12—C11—H11b | 109.1 |
C1—C6—C7 | 123.3 (2) | C10—C11—H11b | 109.1 |
N1—C7—C6 | 127.3 (2) | H11a—C11—H11b | 107.9 |
N1—C8—C13 | 111.5 (2) | C11—C12—H12a | 109.1 |
N1—C8—C9 | 113.5 (2) | C13—C12—H12a | 109.1 |
C13—C8—C9 | 111.1 (2) | C11—C12—H12b | 109.1 |
C8—C9—C10 | 109.8 (3) | C13—C12—H12b | 109.1 |
C11—C10—C9 | 111.4 (3) | H12a—C12—H12b | 107.8 |
C12—C11—C10 | 112.4 (3) | C8—C13—H13a | 109.6 |
C11—C12—C13 | 112.5 (3) | C12—C13—H13a | 109.6 |
C8—C13—C12 | 110.2 (3) | C8—C13—H13b | 109.6 |
C3—C2—H2 | 119.2 | C12—C13—H13b | 109.6 |
C1—C2—H2 | 119.2 | H13a—C13—H13b | 108.1 |
C2—C3—H3 | 120.2 | ||
O1i—Ni1—O1—C1 | −106.0 (2) | O1—C1—C6—C5 | 177.7 (2) |
N1—Ni1—O1—C1 | −3.7 (2) | C2—C1—C6—C5 | −1.2 (4) |
N1i—Ni1—O1—C1 | 151.4 (2) | O1—C1—C6—C7 | −2.5 (4) |
O1—Ni1—N1—C7 | 2.2 (2) | C2—C1—C6—C7 | 178.6 (3) |
O1i—Ni1—N1—C7 | 155.2 (2) | C8—N1—C7—C6 | 179.8 (3) |
N1i—Ni1—N1—C7 | −101.2 (2) | Ni1—N1—C7—C6 | −1.4 (4) |
O1—Ni1—N1—C8 | −179.1 (2) | C5—C6—C7—N1 | −179.1 (3) |
O1i—Ni1—N1—C8 | −26.1 (2) | C1—C6—C7—N1 | 1.1 (5) |
N1i—Ni1—N1—C8 | 77.6 (2) | C7—N1—C8—C13 | −66.0 (3) |
Ni1—O1—C1—C2 | −176.7 (2) | Ni1—N1—C8—C13 | 115.2 (2) |
Ni1—O1—C1—C6 | 4.4 (4) | C7—N1—C8—C9 | 60.4 (3) |
O1—C1—C2—C3 | −178.0 (3) | Ni1—N1—C8—C9 | −118.5 (2) |
C6—C1—C2—C3 | 0.9 (4) | N1—C8—C9—C10 | 175.0 (2) |
C1—C2—C3—C4 | 0.2 (4) | C13—C8—C9—C10 | −58.5 (3) |
C2—C3—C4—C5 | −1.1 (4) | C8—C9—C10—C11 | 55.9 (4) |
C2—C3—C4—Br1 | 179.0 (2) | C9—C10—C11—C12 | −53.3 (4) |
C3—C4—C5—C6 | 0.8 (4) | C10—C11—C12—C13 | 52.5 (5) |
Br1—C4—C5—C6 | −179.4 (2) | N1—C8—C13—C12 | −175.1 (3) |
C4—C5—C6—C1 | 0.4 (4) | C9—C8—C13—C12 | 57.3 (4) |
C4—C5—C6—C7 | −179.4 (3) | C11—C12—C13—C8 | −54.0 (5) |
Symmetry code: (i) −x, y, −z+1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register