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In the title compound, [Ni(NCS)
2(C
16H
23BrN
2O)
2], the Ni atom lies on an inversion centre; it is chelated by the phenolate O and imine N atoms from two Schiff base ligands, and is coordinated by the N atoms from two thiocyanate ligands, giving a slightly distorted octahedral geometry. In the crystal structure, molecules form chains running along the
a axis
via intermolecular N—H
O and N—H
S hydrogen bonds.
Supporting information
CCDC reference: 624995
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.010 Å
- R factor = 0.080
- wR factor = 0.154
- Data-to-parameter ratio = 19.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 46 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 88.00 A 3
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Bis{4-bromo-2-[3-
(cyclohexylamino)propyliminomethyl]phenolato}dithiocyanatonickel(II)
top
Crystal data top
[Ni(NCS)2(C16H23BrN2O)2] | Z = 1 |
Mr = 853.42 | F(000) = 438 |
Triclinic, P1 | Dx = 1.436 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.623 (2) Å | Cell parameters from 897 reflections |
b = 10.732 (2) Å | θ = 2.4–23.8° |
c = 13.036 (3) Å | µ = 2.66 mm−1 |
α = 112.089 (4)° | T = 298 K |
β = 92.535 (4)° | Block, green |
γ = 90.422 (4)° | 0.09 × 0.06 × 0.02 mm |
V = 987.0 (4) Å3 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4360 independent reflections |
Radiation source: fine-focus sealed tube | 1995 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.089 |
ω scans | θmax = 27.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −9→9 |
Tmin = 0.796, Tmax = 0.949 | k = −13→13 |
8527 measured reflections | l = −16→16 |
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)] = 0.081 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.154 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.96 | w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3 |
4360 reflections | (Δ/σ)max < 0.001 |
220 parameters | Δρmax = 0.52 e Å−3 |
3 restraints | Δρmin = −0.42 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 | |
Ni1 | 0.5000 | 0.5000 | 0.5000 | 0.0313 (3) | |
Br1 | 0.82357 (12) | 0.63852 (10) | 1.08108 (7) | 0.0754 (4) | |
S1 | 0.1810 (3) | 0.9010 (2) | 0.65387 (19) | 0.0649 (7) | |
O1 | 0.6708 (5) | 0.6215 (4) | 0.6196 (3) | 0.0362 (11) | |
N1 | 0.3549 (6) | 0.4748 (5) | 0.6218 (4) | 0.0299 (13) | |
N2 | 0.2449 (7) | 0.1477 (5) | 0.4058 (5) | 0.0364 (14) | |
N3 | 0.3440 (8) | 0.6691 (6) | 0.5186 (5) | 0.0453 (16) | |
C1 | 0.5774 (8) | 0.5698 (6) | 0.7723 (5) | 0.0336 (16) | |
C2 | 0.7000 (8) | 0.6191 (6) | 0.7184 (5) | 0.0320 (16) | |
C3 | 0.8634 (8) | 0.6695 (6) | 0.7762 (5) | 0.0377 (17) | |
H3 | 0.9486 | 0.6998 | 0.7415 | 0.045* | |
C4 | 0.8992 (9) | 0.6747 (7) | 0.8821 (6) | 0.0461 (19) | |
H4 | 1.0071 | 0.7090 | 0.9182 | 0.055* | |
C5 | 0.7766 (9) | 0.6298 (7) | 0.9346 (5) | 0.0408 (18) | |
C6 | 0.6173 (9) | 0.5822 (6) | 0.8817 (5) | 0.0390 (17) | |
H6 | 0.5321 | 0.5571 | 0.9196 | 0.047* | |
C7 | 0.4053 (9) | 0.5165 (6) | 0.7248 (5) | 0.0383 (17) | |
H7 | 0.3226 | 0.5120 | 0.7737 | 0.046* | |
C8 | 0.1730 (8) | 0.4202 (7) | 0.5975 (5) | 0.0443 (18) | |
H8A | 0.1321 | 0.4178 | 0.5252 | 0.053* | |
H8B | 0.0976 | 0.4792 | 0.6521 | 0.053* | |
C9 | 0.1596 (9) | 0.2790 (7) | 0.5988 (5) | 0.048 (2) | |
H9A | 0.1810 | 0.2858 | 0.6746 | 0.058* | |
H9B | 0.0399 | 0.2454 | 0.5763 | 0.058* | |
C10 | 0.2813 (9) | 0.1764 (7) | 0.5269 (5) | 0.048 (2) | |
H10A | 0.4017 | 0.2091 | 0.5476 | 0.057* | |
H10B | 0.2682 | 0.0936 | 0.5398 | 0.057* | |
C11 | 0.3305 (9) | 0.0248 (6) | 0.3286 (5) | 0.0399 (17) | |
H11 | 0.4522 | 0.0250 | 0.3562 | 0.048* | |
C12 | 0.2389 (10) | −0.1009 (6) | 0.3255 (6) | 0.052 (2) | |
H12A | 0.1154 | −0.0988 | 0.3051 | 0.062* | |
H12B | 0.2478 | −0.1047 | 0.3987 | 0.062* | |
C13 | 0.3187 (11) | −0.2255 (7) | 0.2430 (7) | 0.068 (2) | |
H13A | 0.4377 | −0.2336 | 0.2689 | 0.082* | |
H13B | 0.2513 | −0.3044 | 0.2389 | 0.082* | |
C14 | 0.3216 (11) | −0.2205 (9) | 0.1284 (7) | 0.076 (3) | |
H14A | 0.3818 | −0.2980 | 0.0796 | 0.091* | |
H14B | 0.2022 | −0.2239 | 0.0983 | 0.091* | |
C15 | 0.4130 (11) | −0.0947 (8) | 0.1336 (7) | 0.073 (3) | |
H15A | 0.4071 | −0.0909 | 0.0604 | 0.087* | |
H15B | 0.5358 | −0.0970 | 0.1555 | 0.087* | |
C16 | 0.3332 (10) | 0.0310 (7) | 0.2148 (6) | 0.056 (2) | |
H16A | 0.4012 | 0.1096 | 0.2189 | 0.067* | |
H16B | 0.2143 | 0.0393 | 0.1888 | 0.067* | |
C17 | 0.2749 (8) | 0.7623 (7) | 0.5746 (6) | 0.0363 (17) | |
H2B | 0.130 (3) | 0.138 (6) | 0.383 (6) | 0.080* | |
H2A | 0.279 (7) | 0.227 (4) | 0.402 (6) | 0.080* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0361 (8) | 0.0294 (7) | 0.0282 (7) | −0.0037 (6) | 0.0026 (6) | 0.0105 (6) |
Br1 | 0.0683 (6) | 0.1264 (9) | 0.0398 (5) | −0.0181 (6) | −0.0112 (4) | 0.0426 (6) |
S1 | 0.0368 (12) | 0.0524 (14) | 0.0843 (17) | 0.0001 (10) | 0.0082 (11) | 0.0010 (12) |
O1 | 0.046 (3) | 0.038 (3) | 0.023 (2) | −0.017 (2) | −0.006 (2) | 0.011 (2) |
N1 | 0.033 (3) | 0.030 (3) | 0.026 (3) | −0.006 (3) | 0.001 (2) | 0.009 (3) |
N2 | 0.038 (3) | 0.033 (4) | 0.034 (3) | −0.004 (3) | 0.000 (3) | 0.008 (3) |
N3 | 0.049 (4) | 0.036 (4) | 0.053 (4) | 0.006 (3) | 0.004 (3) | 0.020 (3) |
C1 | 0.037 (4) | 0.038 (4) | 0.025 (4) | 0.000 (3) | 0.005 (3) | 0.010 (3) |
C2 | 0.041 (4) | 0.023 (4) | 0.027 (4) | 0.002 (3) | 0.002 (3) | 0.004 (3) |
C3 | 0.035 (4) | 0.047 (5) | 0.038 (4) | −0.001 (3) | 0.005 (3) | 0.023 (4) |
C4 | 0.044 (5) | 0.055 (5) | 0.041 (4) | −0.006 (4) | −0.009 (4) | 0.021 (4) |
C5 | 0.046 (5) | 0.052 (5) | 0.029 (4) | 0.001 (4) | −0.002 (3) | 0.021 (4) |
C6 | 0.050 (5) | 0.036 (4) | 0.030 (4) | −0.001 (4) | 0.015 (3) | 0.009 (3) |
C7 | 0.046 (5) | 0.037 (4) | 0.037 (4) | 0.000 (4) | 0.013 (4) | 0.019 (4) |
C8 | 0.038 (4) | 0.055 (5) | 0.033 (4) | −0.002 (4) | 0.004 (3) | 0.008 (4) |
C9 | 0.052 (5) | 0.056 (5) | 0.028 (4) | −0.021 (4) | 0.003 (4) | 0.007 (4) |
C10 | 0.063 (5) | 0.048 (5) | 0.038 (4) | −0.016 (4) | −0.011 (4) | 0.024 (4) |
C11 | 0.039 (4) | 0.037 (4) | 0.045 (4) | 0.000 (3) | 0.003 (3) | 0.016 (4) |
C12 | 0.065 (5) | 0.032 (5) | 0.055 (5) | 0.000 (4) | 0.005 (4) | 0.011 (4) |
C13 | 0.072 (6) | 0.038 (5) | 0.088 (7) | 0.007 (4) | 0.008 (5) | 0.015 (5) |
C14 | 0.073 (6) | 0.063 (7) | 0.069 (7) | 0.013 (5) | 0.008 (5) | −0.002 (5) |
C15 | 0.081 (7) | 0.069 (6) | 0.059 (6) | 0.014 (5) | 0.027 (5) | 0.011 (5) |
C16 | 0.069 (6) | 0.056 (5) | 0.046 (5) | 0.009 (4) | 0.018 (4) | 0.020 (4) |
C17 | 0.024 (4) | 0.044 (5) | 0.048 (5) | −0.012 (3) | −0.004 (3) | 0.027 (4) |
Geometric parameters (Å, º) top
Ni1—O1i | 2.023 (4) | C7—H7 | 0.9300 |
Ni1—O1 | 2.023 (4) | C8—C9 | 1.525 (8) |
Ni1—N1i | 2.072 (5) | C8—H8A | 0.9700 |
Ni1—N1 | 2.072 (5) | C8—H8B | 0.9700 |
Ni1—N3i | 2.120 (6) | C9—C10 | 1.506 (9) |
Ni1—N3 | 2.120 (6) | C9—H9A | 0.9700 |
Br1—C5 | 1.894 (6) | C9—H9B | 0.9700 |
S1—C17 | 1.650 (8) | C10—H10A | 0.9700 |
O1—C2 | 1.307 (7) | C10—H10B | 0.9700 |
N1—C7 | 1.285 (7) | C11—C12 | 1.501 (8) |
N1—C8 | 1.475 (7) | C11—C16 | 1.511 (9) |
N2—C11 | 1.500 (8) | C11—H11 | 0.9800 |
N2—C10 | 1.503 (8) | C12—C13 | 1.517 (9) |
N2—H2B | 0.91 (3) | C12—H12A | 0.9700 |
N2—H2A | 0.91 (5) | C12—H12B | 0.9700 |
N3—C17 | 1.142 (8) | C13—C14 | 1.516 (11) |
C1—C6 | 1.400 (8) | C13—H13A | 0.9700 |
C1—C2 | 1.406 (8) | C13—H13B | 0.9700 |
C1—C7 | 1.443 (8) | C14—C15 | 1.492 (10) |
C2—C3 | 1.418 (8) | C14—H14A | 0.9700 |
C3—C4 | 1.376 (8) | C14—H14B | 0.9700 |
C3—H3 | 0.9300 | C15—C16 | 1.519 (9) |
C4—C5 | 1.368 (9) | C15—H15A | 0.9700 |
C4—H4 | 0.9300 | C15—H15B | 0.9700 |
C5—C6 | 1.365 (9) | C16—H16A | 0.9700 |
C6—H6 | 0.9300 | C16—H16B | 0.9700 |
| | | |
O1i—Ni1—O1 | 180.0 | C9—C8—H8B | 109.3 |
O1i—Ni1—N1i | 89.17 (17) | H8A—C8—H8B | 107.9 |
O1—Ni1—N1i | 90.83 (18) | C10—C9—C8 | 116.8 (6) |
O1i—Ni1—N1 | 90.83 (18) | C10—C9—H9A | 108.1 |
O1—Ni1—N1 | 89.17 (17) | C8—C9—H9A | 108.1 |
N1i—Ni1—N1 | 180.0 | C10—C9—H9B | 108.1 |
O1i—Ni1—N3i | 89.0 (2) | C8—C9—H9B | 108.1 |
O1—Ni1—N3i | 91.0 (2) | H9A—C9—H9B | 107.3 |
N1i—Ni1—N3i | 86.6 (2) | N2—C10—C9 | 112.2 (5) |
N1—Ni1—N3i | 93.4 (2) | N2—C10—H10A | 109.2 |
O1i—Ni1—N3 | 91.0 (2) | C9—C10—H10A | 109.2 |
O1—Ni1—N3 | 89.0 (2) | N2—C10—H10B | 109.2 |
N1i—Ni1—N3 | 93.4 (2) | C9—C10—H10B | 109.2 |
N1—Ni1—N3 | 86.6 (2) | H10A—C10—H10B | 107.9 |
N3i—Ni1—N3 | 180.0 | N2—C11—C12 | 110.9 (5) |
C2—O1—Ni1 | 126.1 (4) | N2—C11—C16 | 109.4 (5) |
C7—N1—C8 | 114.3 (5) | C12—C11—C16 | 111.8 (6) |
C7—N1—Ni1 | 124.2 (4) | N2—C11—H11 | 108.2 |
C8—N1—Ni1 | 121.1 (4) | C12—C11—H11 | 108.2 |
C11—N2—C10 | 114.8 (5) | C16—C11—H11 | 108.2 |
C11—N2—H2B | 105 (5) | C11—C12—C13 | 111.2 (6) |
C10—N2—H2B | 115 (5) | C11—C12—H12A | 109.4 |
C11—N2—H2A | 116 (5) | C13—C12—H12A | 109.4 |
C10—N2—H2A | 101 (5) | C11—C12—H12B | 109.4 |
H2B—N2—H2A | 104 (6) | C13—C12—H12B | 109.4 |
C17—N3—Ni1 | 149.6 (6) | H12A—C12—H12B | 108.0 |
C6—C1—C2 | 118.8 (6) | C14—C13—C12 | 112.0 (7) |
C6—C1—C7 | 117.3 (6) | C14—C13—H13A | 109.2 |
C2—C1—C7 | 123.7 (6) | C12—C13—H13A | 109.2 |
O1—C2—C1 | 123.7 (6) | C14—C13—H13B | 109.2 |
O1—C2—C3 | 119.0 (6) | C12—C13—H13B | 109.2 |
C1—C2—C3 | 117.2 (6) | H13A—C13—H13B | 107.9 |
C4—C3—C2 | 121.8 (6) | C15—C14—C13 | 110.4 (7) |
C4—C3—H3 | 119.1 | C15—C14—H14A | 109.6 |
C2—C3—H3 | 119.1 | C13—C14—H14A | 109.6 |
C5—C4—C3 | 120.3 (6) | C15—C14—H14B | 109.6 |
C5—C4—H4 | 119.9 | C13—C14—H14B | 109.6 |
C3—C4—H4 | 119.9 | H14A—C14—H14B | 108.1 |
C6—C5—C4 | 119.4 (6) | C14—C15—C16 | 112.5 (7) |
C6—C5—Br1 | 120.0 (5) | C14—C15—H15A | 109.1 |
C4—C5—Br1 | 120.6 (5) | C16—C15—H15A | 109.1 |
C5—C6—C1 | 122.4 (6) | C14—C15—H15B | 109.1 |
C5—C6—H6 | 118.8 | C16—C15—H15B | 109.1 |
C1—C6—H6 | 118.8 | H15A—C15—H15B | 107.8 |
N1—C7—C1 | 126.6 (6) | C11—C16—C15 | 110.6 (6) |
N1—C7—H7 | 116.7 | C11—C16—H16A | 109.5 |
C1—C7—H7 | 116.7 | C15—C16—H16A | 109.5 |
N1—C8—C9 | 111.7 (5) | C11—C16—H16B | 109.5 |
N1—C8—H8A | 109.3 | C15—C16—H16B | 109.5 |
C9—C8—H8A | 109.3 | H16A—C16—H16B | 108.1 |
N1—C8—H8B | 109.3 | N3—C17—S1 | 177.5 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.91 (5) | 1.79 (5) | 2.697 (7) | 173 (6) |
N2—H2B···S1ii | 0.91 (3) | 2.40 (2) | 3.296 (6) | 171 (6) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
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