In the asymmetric unit of the title ion-pair complex, (C
25H
20BrFP)
2[Ni(C
4N
2S
2)
2], there is one 4-bromo-2-fluorobenzyl)triphenylphosphonium cation, (BrFBzTPP)
+, and one-half of an [Ni(mnt)
2]
2− anion (mnt is maleonitriledithiolate), which lies on an inversion site. The Ni
II ion is coordinated by four S atoms of two mnt
2− ligands in a square-planar geometry. The (BrFBzTPP)
+ cation adopts a tetrahedral configuration about P. The cations and anions are linked by weak C—H
N and C—H
S interactions.
Supporting information
CCDC reference: 628014
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.014 Å
- R factor = 0.086
- wR factor = 0.294
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C
RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25
Weighted R factor given 0.294
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT084_ALERT_2_C High R2 Value .................................. 0.29
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.03
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C1 - C2 ... 1.43 Ang.
PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C3 - C4 ... 1.44 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1
S1 -NI1 -S1 -C2 12.00 0.00 3.556 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6
S2 -NI1 -S2 -C3 5.00 0.00 3.556 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 7
N1 -C1 -C2 -C3 14.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8
N1 -C1 -C2 -S1 4.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 17
C2 -C3 -C4 -N2 3.00 0.00 1.555 1.555 1.555 1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18
S2 -C3 -C4 -N2 15.00 0.00 1.555 1.555 1.555 1.555
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C58 H40 Br2 F2 N4 Ni1 P2 S4
Atom count from _chemical_formula_moiety:C50 H40 Br2 F2 P2
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
3 ALERT level G = General alerts; check
4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
6 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-fluorobenzyl)triphenylphosphonium]
bis(1,2-dicyanoethene-1,2-dithiolato)nickelate(II)
top
Crystal data top
(C25H20BrFP)2·[Ni(C4N2S2)2] | F(000) = 1252 |
Mr = 1239.65 | Dx = 1.486 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2698 reflections |
a = 11.210 (2) Å | θ = 2.5–20.0° |
b = 28.436 (6) Å | µ = 2.05 mm−1 |
c = 9.604 (2) Å | T = 293 K |
β = 115.18 (3)° | Block, red |
V = 2770.5 (12) Å3 | 0.38 × 0.24 × 0.15 mm |
Z = 2 | |
Data collection top
Bruker SMART area-detector diffractometer | 4860 independent reflections |
Radiation source: fine-focus sealed tube | 3073 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→13 |
Tmin = 0.562, Tmax = 0.736 | k = −27→33 |
14846 measured reflections | l = −11→11 |
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)] = 0.086 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.294 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.18P)2 + 1.8P] where P = (Fo2 + 2Fc2)/3 |
4860 reflections | (Δ/σ)max < 0.001 |
331 parameters | Δρmax = 1.93 e Å−3 |
0 restraints | Δρmin = −1.39 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.0000 | 0.0000 | 0.5000 | 0.0668 (4) | |
P1 | 0.6816 (2) | 0.37863 (6) | 0.0172 (2) | 0.0784 (6) | |
S1 | 0.08850 (19) | 0.05582 (7) | 0.42280 (18) | 0.0822 (6) | |
S2 | 0.10009 (19) | 0.02253 (7) | 0.73864 (17) | 0.0802 (6) | |
F1 | 0.7800 (6) | 0.2926 (2) | −0.1916 (5) | 0.1267 (18) | |
N1 | 0.3233 (9) | 0.1563 (3) | 0.5771 (10) | 0.129 (3) | |
N2 | 0.3337 (10) | 0.1147 (3) | 0.9738 (9) | 0.145 (3) | |
Br1 | 1.08501 (18) | 0.17985 (8) | 0.2198 (3) | 0.2396 (12) | |
C1 | 0.2618 (9) | 0.1244 (4) | 0.5845 (10) | 0.103 (3) | |
C2 | 0.1865 (7) | 0.0848 (3) | 0.5919 (8) | 0.0801 (18) | |
C3 | 0.1919 (7) | 0.0705 (2) | 0.7276 (8) | 0.0759 (17) | |
C4 | 0.2708 (9) | 0.0952 (3) | 0.8671 (9) | 0.099 (2) | |
C5 | 0.8704 (8) | 0.2879 (4) | −0.0442 (10) | 0.100 (2) | |
C6 | 0.9200 (9) | 0.2453 (4) | −0.0019 (12) | 0.120 (3) | |
H6 | 0.8939 | 0.2196 | −0.0683 | 0.144* | |
C7 | 1.0150 (11) | 0.2418 (5) | 0.1512 (19) | 0.145 (4) | |
C8 | 1.0598 (10) | 0.2767 (7) | 0.2475 (13) | 0.142 (5) | |
H8 | 1.1276 | 0.2728 | 0.3453 | 0.170* | |
C9 | 0.9987 (10) | 0.3215 (5) | 0.1944 (10) | 0.123 (4) | |
H9 | 1.0254 | 0.3471 | 0.2608 | 0.148* | |
C10 | 0.9006 (8) | 0.3276 (3) | 0.0463 (9) | 0.094 (2) | |
C11 | 0.8322 (9) | 0.3722 (3) | −0.0113 (10) | 0.098 (3) | |
H11A | 0.8099 | 0.3746 | −0.1204 | 0.118* | |
H11B | 0.8916 | 0.3979 | 0.0403 | 0.118* | |
C12 | 0.6205 (8) | 0.2861 (2) | 0.0438 (8) | 0.084 (2) | |
H12 | 0.6889 | 0.2870 | 0.1422 | 0.100* | |
C13 | 0.5527 (8) | 0.2452 (2) | −0.0121 (9) | 0.088 (2) | |
H13 | 0.5761 | 0.2183 | 0.0487 | 0.105* | |
C14 | 0.4524 (8) | 0.2432 (3) | −0.1539 (10) | 0.093 (2) | |
H14 | 0.4067 | 0.2152 | −0.1888 | 0.111* | |
C15 | 0.4173 (8) | 0.2820 (3) | −0.2469 (9) | 0.091 (2) | |
H15 | 0.3485 | 0.2805 | −0.3449 | 0.109* | |
C16 | 0.4855 (7) | 0.3237 (3) | −0.1931 (7) | 0.0798 (18) | |
H16 | 0.4630 | 0.3503 | −0.2556 | 0.096* | |
C17 | 0.5869 (7) | 0.3259 (2) | −0.0468 (7) | 0.0674 (16) | |
C18 | 0.4635 (12) | 0.4344 (3) | −0.0991 (11) | 0.113 (3) | |
H18 | 0.4343 | 0.4153 | −0.0415 | 0.135* | |
C19 | 0.3819 (12) | 0.4694 (3) | −0.1889 (12) | 0.119 (3) | |
H19 | 0.2989 | 0.4743 | −0.1914 | 0.143* | |
C20 | 0.4273 (15) | 0.4970 (3) | −0.2752 (14) | 0.129 (4) | |
H20 | 0.3734 | 0.5204 | −0.3382 | 0.155* | |
C21 | 0.5476 (14) | 0.4903 (4) | −0.2691 (12) | 0.123 (4) | |
H21 | 0.5755 | 0.5094 | −0.3280 | 0.148* | |
C22 | 0.6322 (10) | 0.4557 (3) | −0.1776 (9) | 0.100 (3) | |
H22 | 0.7161 | 0.4517 | −0.1733 | 0.119* | |
C23 | 0.5863 (9) | 0.4271 (2) | −0.0925 (8) | 0.086 (2) | |
C24 | 0.6530 (8) | 0.3705 (2) | 0.2884 (8) | 0.0814 (19) | |
H24 | 0.5782 | 0.3527 | 0.2325 | 0.098* | |
C25 | 0.6889 (10) | 0.3801 (3) | 0.4429 (9) | 0.101 (3) | |
H25 | 0.6381 | 0.3684 | 0.4903 | 0.122* | |
C26 | 0.7967 (11) | 0.4064 (3) | 0.5252 (10) | 0.116 (3) | |
H26 | 0.8200 | 0.4122 | 0.6288 | 0.140* | |
C27 | 0.8708 (10) | 0.4240 (4) | 0.4572 (11) | 0.125 (3) | |
H27 | 0.9450 | 0.4420 | 0.5145 | 0.150* | |
C28 | 0.8372 (9) | 0.4158 (3) | 0.3042 (10) | 0.114 (3) | |
H28 | 0.8866 | 0.4289 | 0.2570 | 0.136* | |
C29 | 0.7281 (8) | 0.3874 (2) | 0.2197 (8) | 0.084 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0688 (7) | 0.0706 (8) | 0.0498 (6) | 0.0167 (5) | 0.0147 (5) | −0.0044 (5) |
P1 | 0.1049 (15) | 0.0754 (12) | 0.0653 (10) | −0.0243 (9) | 0.0462 (10) | −0.0101 (8) |
S1 | 0.0884 (13) | 0.0932 (13) | 0.0549 (9) | −0.0004 (9) | 0.0209 (9) | −0.0071 (8) |
S2 | 0.0900 (12) | 0.0858 (12) | 0.0525 (9) | 0.0128 (9) | 0.0185 (8) | −0.0046 (8) |
F1 | 0.130 (4) | 0.147 (5) | 0.077 (3) | 0.023 (3) | 0.019 (3) | −0.033 (3) |
N1 | 0.136 (7) | 0.135 (7) | 0.110 (6) | −0.043 (6) | 0.046 (5) | −0.030 (5) |
N2 | 0.165 (8) | 0.143 (7) | 0.076 (5) | 0.003 (6) | 0.002 (5) | −0.030 (5) |
Br1 | 0.1523 (15) | 0.252 (2) | 0.307 (3) | 0.0844 (13) | 0.0902 (16) | 0.1315 (19) |
C1 | 0.090 (6) | 0.122 (7) | 0.080 (5) | −0.018 (5) | 0.020 (4) | −0.025 (5) |
C2 | 0.072 (4) | 0.089 (5) | 0.068 (4) | 0.009 (4) | 0.018 (3) | −0.012 (3) |
C3 | 0.074 (4) | 0.075 (4) | 0.065 (4) | 0.011 (3) | 0.016 (3) | −0.010 (3) |
C4 | 0.114 (6) | 0.090 (5) | 0.064 (4) | 0.002 (4) | 0.010 (4) | −0.013 (4) |
C5 | 0.082 (5) | 0.129 (7) | 0.083 (5) | −0.001 (5) | 0.029 (4) | −0.018 (5) |
C6 | 0.077 (6) | 0.164 (10) | 0.110 (7) | 0.018 (6) | 0.031 (5) | −0.001 (6) |
C7 | 0.074 (7) | 0.191 (13) | 0.171 (12) | 0.022 (7) | 0.053 (8) | 0.061 (10) |
C8 | 0.068 (6) | 0.240 (17) | 0.094 (7) | −0.012 (8) | 0.012 (5) | 0.026 (9) |
C9 | 0.082 (6) | 0.207 (12) | 0.075 (5) | −0.050 (7) | 0.029 (5) | −0.019 (6) |
C10 | 0.088 (5) | 0.122 (7) | 0.080 (5) | −0.036 (5) | 0.043 (4) | −0.020 (5) |
C11 | 0.113 (6) | 0.112 (7) | 0.088 (5) | −0.032 (5) | 0.060 (5) | −0.018 (5) |
C12 | 0.112 (6) | 0.069 (4) | 0.071 (4) | −0.016 (4) | 0.040 (4) | −0.012 (3) |
C13 | 0.110 (6) | 0.064 (4) | 0.091 (5) | −0.010 (4) | 0.045 (5) | −0.006 (4) |
C14 | 0.100 (6) | 0.074 (5) | 0.104 (6) | −0.012 (4) | 0.044 (5) | −0.021 (4) |
C15 | 0.084 (5) | 0.102 (6) | 0.071 (4) | −0.005 (4) | 0.019 (4) | −0.018 (4) |
C16 | 0.089 (5) | 0.086 (5) | 0.059 (4) | −0.005 (4) | 0.026 (4) | −0.003 (3) |
C17 | 0.081 (4) | 0.069 (4) | 0.055 (3) | −0.006 (3) | 0.031 (3) | −0.005 (3) |
C18 | 0.179 (10) | 0.081 (5) | 0.116 (7) | 0.003 (6) | 0.099 (7) | 0.016 (5) |
C19 | 0.168 (9) | 0.087 (6) | 0.128 (7) | 0.016 (6) | 0.087 (7) | 0.022 (5) |
C20 | 0.195 (13) | 0.077 (6) | 0.128 (8) | −0.001 (6) | 0.080 (9) | 0.021 (5) |
C21 | 0.178 (11) | 0.098 (7) | 0.107 (7) | −0.044 (7) | 0.075 (8) | 0.003 (5) |
C22 | 0.141 (7) | 0.080 (5) | 0.086 (5) | −0.033 (5) | 0.057 (5) | 0.000 (4) |
C23 | 0.130 (7) | 0.072 (4) | 0.075 (4) | −0.019 (4) | 0.061 (5) | −0.006 (3) |
C24 | 0.110 (6) | 0.075 (4) | 0.062 (4) | −0.017 (4) | 0.040 (4) | −0.007 (3) |
C25 | 0.135 (7) | 0.104 (6) | 0.076 (5) | −0.028 (5) | 0.055 (5) | −0.008 (4) |
C26 | 0.154 (9) | 0.120 (7) | 0.074 (5) | −0.028 (6) | 0.048 (6) | −0.027 (5) |
C27 | 0.117 (7) | 0.156 (9) | 0.101 (6) | −0.049 (7) | 0.044 (6) | −0.054 (6) |
C28 | 0.117 (7) | 0.144 (8) | 0.091 (6) | −0.059 (6) | 0.055 (5) | −0.047 (5) |
C29 | 0.108 (6) | 0.077 (4) | 0.072 (4) | −0.030 (4) | 0.044 (4) | −0.017 (3) |
Geometric parameters (Å, º) top
Ni1—S1 | 2.163 (2) | C12—H12 | 0.9300 |
Ni1—S1i | 2.163 (2) | C13—C14 | 1.348 (11) |
Ni1—S2i | 2.1758 (17) | C13—H13 | 0.9300 |
Ni1—S2 | 2.1758 (17) | C14—C15 | 1.369 (11) |
P1—C23 | 1.787 (8) | C14—H14 | 0.9300 |
P1—C17 | 1.788 (6) | C15—C16 | 1.386 (10) |
P1—C29 | 1.804 (7) | C15—H15 | 0.9300 |
P1—C11 | 1.832 (8) | C16—C17 | 1.382 (9) |
S1—C2 | 1.733 (7) | C16—H16 | 0.9300 |
S2—C3 | 1.738 (8) | C18—C23 | 1.366 (13) |
F1—C5 | 1.352 (10) | C18—C19 | 1.377 (13) |
N1—C1 | 1.159 (11) | C18—H18 | 0.9300 |
N2—C4 | 1.113 (10) | C19—C20 | 1.386 (13) |
Br1—C7 | 1.926 (13) | C19—H19 | 0.9300 |
C1—C2 | 1.428 (12) | C20—C21 | 1.339 (16) |
C2—C3 | 1.342 (10) | C20—H20 | 0.9300 |
C3—C4 | 1.437 (10) | C21—C22 | 1.389 (15) |
C5—C6 | 1.323 (13) | C21—H21 | 0.9300 |
C5—C10 | 1.377 (11) | C22—C23 | 1.398 (10) |
C6—C7 | 1.405 (16) | C22—H22 | 0.9300 |
C6—H6 | 0.9300 | C24—C29 | 1.359 (10) |
C7—C8 | 1.303 (18) | C24—C25 | 1.389 (10) |
C8—C9 | 1.433 (17) | C24—H24 | 0.9300 |
C8—H8 | 0.9300 | C25—C26 | 1.352 (12) |
C9—C10 | 1.389 (13) | C25—H25 | 0.9300 |
C9—H9 | 0.9300 | C26—C27 | 1.352 (12) |
C10—C11 | 1.462 (12) | C26—H26 | 0.9300 |
C11—H11A | 0.9700 | C27—C28 | 1.373 (12) |
C11—H11B | 0.9700 | C27—H27 | 0.9300 |
C12—C13 | 1.369 (9) | C28—C29 | 1.400 (10) |
C12—C17 | 1.379 (9) | C28—H28 | 0.9300 |
| | | |
S1—Ni1—S1i | 180.00 (11) | C14—C13—H13 | 119.4 |
S1—Ni1—S2i | 87.77 (7) | C12—C13—H13 | 119.4 |
S1i—Ni1—S2i | 92.23 (7) | C13—C14—C15 | 120.7 (7) |
S1—Ni1—S2 | 92.23 (7) | C13—C14—H14 | 119.7 |
S1i—Ni1—S2 | 87.77 (7) | C15—C14—H14 | 119.7 |
S2i—Ni1—S2 | 180.0 | C14—C15—C16 | 119.2 (7) |
C23—P1—C17 | 109.0 (3) | C14—C15—H15 | 120.4 |
C23—P1—C29 | 110.8 (4) | C16—C15—H15 | 120.4 |
C17—P1—C29 | 110.1 (3) | C17—C16—C15 | 120.1 (7) |
C23—P1—C11 | 110.3 (4) | C17—C16—H16 | 119.9 |
C17—P1—C11 | 108.4 (3) | C15—C16—H16 | 119.9 |
C29—P1—C11 | 108.3 (4) | C12—C17—C16 | 119.4 (6) |
C2—S1—Ni1 | 103.2 (3) | C12—C17—P1 | 120.6 (5) |
C3—S2—Ni1 | 102.7 (2) | C16—C17—P1 | 119.9 (5) |
N1—C1—C2 | 179.0 (10) | C23—C18—C19 | 121.8 (8) |
C3—C2—C1 | 120.3 (7) | C23—C18—H18 | 119.1 |
C3—C2—S1 | 121.0 (6) | C19—C18—H18 | 119.1 |
C1—C2—S1 | 118.8 (6) | C18—C19—C20 | 117.8 (11) |
C2—C3—C4 | 120.8 (7) | C18—C19—H19 | 121.1 |
C2—C3—S2 | 120.9 (5) | C20—C19—H19 | 121.1 |
C4—C3—S2 | 118.2 (6) | C21—C20—C19 | 120.9 (11) |
N2—C4—C3 | 178.5 (12) | C21—C20—H20 | 119.6 |
C6—C5—F1 | 116.3 (8) | C19—C20—H20 | 119.6 |
C6—C5—C10 | 126.8 (9) | C20—C21—C22 | 122.2 (9) |
F1—C5—C10 | 116.9 (9) | C20—C21—H21 | 118.9 |
C5—C6—C7 | 114.8 (11) | C22—C21—H21 | 118.9 |
C5—C6—H6 | 122.6 | C21—C22—C23 | 117.3 (9) |
C7—C6—H6 | 122.6 | C21—C22—H22 | 121.3 |
C8—C7—C6 | 125.5 (13) | C23—C22—H22 | 121.3 |
C8—C7—Br1 | 118.4 (12) | C18—C23—C22 | 119.9 (8) |
C6—C7—Br1 | 116.1 (13) | C18—C23—P1 | 118.9 (6) |
C7—C8—C9 | 116.3 (11) | C22—C23—P1 | 121.1 (7) |
C7—C8—H8 | 121.9 | C29—C24—C25 | 119.4 (7) |
C9—C8—H8 | 121.9 | C29—C24—H24 | 120.3 |
C10—C9—C8 | 121.8 (11) | C25—C24—H24 | 120.3 |
C10—C9—H9 | 119.1 | C26—C25—C24 | 120.9 (8) |
C8—C9—H9 | 119.1 | C26—C25—H25 | 119.5 |
C5—C10—C9 | 114.7 (10) | C24—C25—H25 | 119.5 |
C5—C10—C11 | 121.5 (8) | C27—C26—C25 | 120.1 (8) |
C9—C10—C11 | 123.8 (9) | C27—C26—H26 | 119.9 |
C10—C11—P1 | 113.5 (5) | C25—C26—H26 | 119.9 |
C10—C11—H11A | 108.9 | C26—C27—C28 | 120.5 (8) |
P1—C11—H11A | 108.9 | C26—C27—H27 | 119.7 |
C10—C11—H11B | 108.9 | C28—C27—H27 | 119.7 |
P1—C11—H11B | 108.9 | C27—C28—C29 | 119.5 (8) |
H11A—C11—H11B | 107.7 | C27—C28—H28 | 120.3 |
C13—C12—C17 | 119.5 (7) | C29—C28—H28 | 120.3 |
C13—C12—H12 | 120.2 | C24—C29—C28 | 119.4 (7) |
C17—C12—H12 | 120.2 | C24—C29—P1 | 121.3 (5) |
C14—C13—C12 | 121.1 (7) | C28—C29—P1 | 119.0 (6) |
| | | |
S1i—Ni1—S1—C2 | 117 (100) | C14—C15—C16—C17 | −0.6 (11) |
S2i—Ni1—S1—C2 | −179.3 (2) | C13—C12—C17—C16 | −0.3 (11) |
S2—Ni1—S1—C2 | 0.7 (2) | C13—C12—C17—P1 | −175.2 (6) |
S1—Ni1—S2—C3 | −0.8 (2) | C15—C16—C17—C12 | 1.0 (11) |
S1i—Ni1—S2—C3 | 179.2 (2) | C15—C16—C17—P1 | 175.9 (6) |
S2i—Ni1—S2—C3 | 52 (31) | C23—P1—C17—C12 | −161.9 (5) |
N1—C1—C2—C3 | 138 (69) | C29—P1—C17—C12 | −40.2 (7) |
N1—C1—C2—S1 | −43 (69) | C11—P1—C17—C12 | 78.0 (6) |
Ni1—S1—C2—C3 | −0.3 (6) | C23—P1—C17—C16 | 23.2 (7) |
Ni1—S1—C2—C1 | 179.8 (6) | C29—P1—C17—C16 | 144.9 (6) |
C1—C2—C3—C4 | 1.4 (11) | C11—P1—C17—C16 | −96.9 (6) |
S1—C2—C3—C4 | −178.5 (6) | C23—C18—C19—C20 | 0.9 (15) |
C1—C2—C3—S2 | 179.5 (6) | C18—C19—C20—C21 | −1.2 (17) |
S1—C2—C3—S2 | −0.4 (8) | C19—C20—C21—C22 | 0.3 (18) |
Ni1—S2—C3—C2 | 0.8 (6) | C20—C21—C22—C23 | 1.0 (14) |
Ni1—S2—C3—C4 | 179.0 (5) | C19—C18—C23—C22 | 0.4 (14) |
C2—C3—C4—N2 | −30 (40) | C19—C18—C23—P1 | −176.1 (8) |
S2—C3—C4—N2 | 152 (39) | C21—C22—C23—C18 | −1.3 (12) |
F1—C5—C6—C7 | 179.1 (8) | C21—C22—C23—P1 | 175.1 (7) |
C10—C5—C6—C7 | −1.4 (14) | C17—P1—C23—C18 | 54.2 (7) |
C5—C6—C7—C8 | −3.2 (16) | C29—P1—C23—C18 | −67.1 (8) |
C5—C6—C7—Br1 | 177.8 (7) | C11—P1—C23—C18 | 173.1 (7) |
C6—C7—C8—C9 | 4.9 (18) | C17—P1—C23—C22 | −122.2 (6) |
Br1—C7—C8—C9 | −176.1 (7) | C29—P1—C23—C22 | 116.5 (6) |
C7—C8—C9—C10 | −2.3 (16) | C11—P1—C23—C22 | −3.3 (7) |
C6—C5—C10—C9 | 3.5 (13) | C29—C24—C25—C26 | 0.6 (14) |
F1—C5—C10—C9 | −177.0 (7) | C24—C25—C26—C27 | 0.6 (16) |
C6—C5—C10—C11 | −175.8 (9) | C25—C26—C27—C28 | 0.2 (18) |
F1—C5—C10—C11 | 3.7 (11) | C26—C27—C28—C29 | −2.2 (17) |
C8—C9—C10—C5 | −1.5 (13) | C25—C24—C29—C28 | −2.5 (13) |
C8—C9—C10—C11 | 177.8 (8) | C25—C24—C29—P1 | −176.8 (7) |
C5—C10—C11—P1 | 88.1 (8) | C27—C28—C29—C24 | 3.4 (15) |
C9—C10—C11—P1 | −91.2 (9) | C27—C28—C29—P1 | 177.8 (8) |
C23—P1—C11—C10 | −167.2 (5) | C23—P1—C29—C24 | 92.6 (7) |
C17—P1—C11—C10 | −48.0 (7) | C17—P1—C29—C24 | −28.0 (8) |
C29—P1—C11—C10 | 71.4 (6) | C11—P1—C29—C24 | −146.3 (7) |
C17—C12—C13—C14 | −0.7 (12) | C23—P1—C29—C28 | −81.7 (8) |
C12—C13—C14—C15 | 1.1 (13) | C17—P1—C29—C28 | 157.7 (7) |
C13—C14—C15—C16 | −0.5 (12) | C11—P1—C29—C28 | 39.4 (9) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···N2ii | 0.93 | 2.58 | 3.400 (11) | 148 |
C24—H24···N1iii | 0.93 | 2.61 | 3.460 (13) | 152 |
C28—H28···S2iv | 0.93 | 2.83 | 3.706 (9) | 157 |
Symmetry codes: (ii) x, −y+1/2, z−3/2; (iii) x, −y+1/2, z−1/2; (iv) x+1, −y+1/2, z−1/2. |