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In the asymmetric unit of the title ion-pair complex, (C25H20BrFP)2[Ni(C4N2S2)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 NiII ion is coordinated by four S atoms of two mnt2− 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806040359/ng2114sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806040359/ng2114Isup2.hkl
Contains datablock I

CCDC reference: 628014

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Computing details top

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 = 1239.65Dx = 1.486 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2698 reflections
a = 11.210 (2) Åθ = 2.5–20.0°
b = 28.436 (6) ŵ = 2.05 mm1
c = 9.604 (2) ÅT = 293 K
β = 115.18 (3)°Block, red
V = 2770.5 (12) Å30.38 × 0.24 × 0.15 mm
Z = 2
Data collection top
Bruker SMART area-detector
diffractometer
4860 independent reflections
Radiation source: fine-focus sealed tube3073 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1313
Tmin = 0.562, Tmax = 0.736k = 2733
14846 measured reflectionsl = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.294H-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 parametersΔρmax = 1.93 e Å3
0 restraintsΔρmin = 1.39 e Å3
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
xyzUiso*/Ueq
Ni10.00000.00000.50000.0668 (4)
P10.6816 (2)0.37863 (6)0.0172 (2)0.0784 (6)
S10.08850 (19)0.05582 (7)0.42280 (18)0.0822 (6)
S20.10009 (19)0.02253 (7)0.73864 (17)0.0802 (6)
F10.7800 (6)0.2926 (2)0.1916 (5)0.1267 (18)
N10.3233 (9)0.1563 (3)0.5771 (10)0.129 (3)
N20.3337 (10)0.1147 (3)0.9738 (9)0.145 (3)
Br11.08501 (18)0.17985 (8)0.2198 (3)0.2396 (12)
C10.2618 (9)0.1244 (4)0.5845 (10)0.103 (3)
C20.1865 (7)0.0848 (3)0.5919 (8)0.0801 (18)
C30.1919 (7)0.0705 (2)0.7276 (8)0.0759 (17)
C40.2708 (9)0.0952 (3)0.8671 (9)0.099 (2)
C50.8704 (8)0.2879 (4)0.0442 (10)0.100 (2)
C60.9200 (9)0.2453 (4)0.0019 (12)0.120 (3)
H60.89390.21960.06830.144*
C71.0150 (11)0.2418 (5)0.1512 (19)0.145 (4)
C81.0598 (10)0.2767 (7)0.2475 (13)0.142 (5)
H81.12760.27280.34530.170*
C90.9987 (10)0.3215 (5)0.1944 (10)0.123 (4)
H91.02540.34710.26080.148*
C100.9006 (8)0.3276 (3)0.0463 (9)0.094 (2)
C110.8322 (9)0.3722 (3)0.0113 (10)0.098 (3)
H11A0.80990.37460.12040.118*
H11B0.89160.39790.04030.118*
C120.6205 (8)0.2861 (2)0.0438 (8)0.084 (2)
H120.68890.28700.14220.100*
C130.5527 (8)0.2452 (2)0.0121 (9)0.088 (2)
H130.57610.21830.04870.105*
C140.4524 (8)0.2432 (3)0.1539 (10)0.093 (2)
H140.40670.21520.18880.111*
C150.4173 (8)0.2820 (3)0.2469 (9)0.091 (2)
H150.34850.28050.34490.109*
C160.4855 (7)0.3237 (3)0.1931 (7)0.0798 (18)
H160.46300.35030.25560.096*
C170.5869 (7)0.3259 (2)0.0468 (7)0.0674 (16)
C180.4635 (12)0.4344 (3)0.0991 (11)0.113 (3)
H180.43430.41530.04150.135*
C190.3819 (12)0.4694 (3)0.1889 (12)0.119 (3)
H190.29890.47430.19140.143*
C200.4273 (15)0.4970 (3)0.2752 (14)0.129 (4)
H200.37340.52040.33820.155*
C210.5476 (14)0.4903 (4)0.2691 (12)0.123 (4)
H210.57550.50940.32800.148*
C220.6322 (10)0.4557 (3)0.1776 (9)0.100 (3)
H220.71610.45170.17330.119*
C230.5863 (9)0.4271 (2)0.0925 (8)0.086 (2)
C240.6530 (8)0.3705 (2)0.2884 (8)0.0814 (19)
H240.57820.35270.23250.098*
C250.6889 (10)0.3801 (3)0.4429 (9)0.101 (3)
H250.63810.36840.49030.122*
C260.7967 (11)0.4064 (3)0.5252 (10)0.116 (3)
H260.82000.41220.62880.140*
C270.8708 (10)0.4240 (4)0.4572 (11)0.125 (3)
H270.94500.44200.51450.150*
C280.8372 (9)0.4158 (3)0.3042 (10)0.114 (3)
H280.88660.42890.25700.136*
C290.7281 (8)0.3874 (2)0.2197 (8)0.084 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0688 (7)0.0706 (8)0.0498 (6)0.0167 (5)0.0147 (5)0.0044 (5)
P10.1049 (15)0.0754 (12)0.0653 (10)0.0243 (9)0.0462 (10)0.0101 (8)
S10.0884 (13)0.0932 (13)0.0549 (9)0.0004 (9)0.0209 (9)0.0071 (8)
S20.0900 (12)0.0858 (12)0.0525 (9)0.0128 (9)0.0185 (8)0.0046 (8)
F10.130 (4)0.147 (5)0.077 (3)0.023 (3)0.019 (3)0.033 (3)
N10.136 (7)0.135 (7)0.110 (6)0.043 (6)0.046 (5)0.030 (5)
N20.165 (8)0.143 (7)0.076 (5)0.003 (6)0.002 (5)0.030 (5)
Br10.1523 (15)0.252 (2)0.307 (3)0.0844 (13)0.0902 (16)0.1315 (19)
C10.090 (6)0.122 (7)0.080 (5)0.018 (5)0.020 (4)0.025 (5)
C20.072 (4)0.089 (5)0.068 (4)0.009 (4)0.018 (3)0.012 (3)
C30.074 (4)0.075 (4)0.065 (4)0.011 (3)0.016 (3)0.010 (3)
C40.114 (6)0.090 (5)0.064 (4)0.002 (4)0.010 (4)0.013 (4)
C50.082 (5)0.129 (7)0.083 (5)0.001 (5)0.029 (4)0.018 (5)
C60.077 (6)0.164 (10)0.110 (7)0.018 (6)0.031 (5)0.001 (6)
C70.074 (7)0.191 (13)0.171 (12)0.022 (7)0.053 (8)0.061 (10)
C80.068 (6)0.240 (17)0.094 (7)0.012 (8)0.012 (5)0.026 (9)
C90.082 (6)0.207 (12)0.075 (5)0.050 (7)0.029 (5)0.019 (6)
C100.088 (5)0.122 (7)0.080 (5)0.036 (5)0.043 (4)0.020 (5)
C110.113 (6)0.112 (7)0.088 (5)0.032 (5)0.060 (5)0.018 (5)
C120.112 (6)0.069 (4)0.071 (4)0.016 (4)0.040 (4)0.012 (3)
C130.110 (6)0.064 (4)0.091 (5)0.010 (4)0.045 (5)0.006 (4)
C140.100 (6)0.074 (5)0.104 (6)0.012 (4)0.044 (5)0.021 (4)
C150.084 (5)0.102 (6)0.071 (4)0.005 (4)0.019 (4)0.018 (4)
C160.089 (5)0.086 (5)0.059 (4)0.005 (4)0.026 (4)0.003 (3)
C170.081 (4)0.069 (4)0.055 (3)0.006 (3)0.031 (3)0.005 (3)
C180.179 (10)0.081 (5)0.116 (7)0.003 (6)0.099 (7)0.016 (5)
C190.168 (9)0.087 (6)0.128 (7)0.016 (6)0.087 (7)0.022 (5)
C200.195 (13)0.077 (6)0.128 (8)0.001 (6)0.080 (9)0.021 (5)
C210.178 (11)0.098 (7)0.107 (7)0.044 (7)0.075 (8)0.003 (5)
C220.141 (7)0.080 (5)0.086 (5)0.033 (5)0.057 (5)0.000 (4)
C230.130 (7)0.072 (4)0.075 (4)0.019 (4)0.061 (5)0.006 (3)
C240.110 (6)0.075 (4)0.062 (4)0.017 (4)0.040 (4)0.007 (3)
C250.135 (7)0.104 (6)0.076 (5)0.028 (5)0.055 (5)0.008 (4)
C260.154 (9)0.120 (7)0.074 (5)0.028 (6)0.048 (6)0.027 (5)
C270.117 (7)0.156 (9)0.101 (6)0.049 (7)0.044 (6)0.054 (6)
C280.117 (7)0.144 (8)0.091 (6)0.059 (6)0.055 (5)0.047 (5)
C290.108 (6)0.077 (4)0.072 (4)0.030 (4)0.044 (4)0.017 (3)
Geometric parameters (Å, º) top
Ni1—S12.163 (2)C12—H120.9300
Ni1—S1i2.163 (2)C13—C141.348 (11)
Ni1—S2i2.1758 (17)C13—H130.9300
Ni1—S22.1758 (17)C14—C151.369 (11)
P1—C231.787 (8)C14—H140.9300
P1—C171.788 (6)C15—C161.386 (10)
P1—C291.804 (7)C15—H150.9300
P1—C111.832 (8)C16—C171.382 (9)
S1—C21.733 (7)C16—H160.9300
S2—C31.738 (8)C18—C231.366 (13)
F1—C51.352 (10)C18—C191.377 (13)
N1—C11.159 (11)C18—H180.9300
N2—C41.113 (10)C19—C201.386 (13)
Br1—C71.926 (13)C19—H190.9300
C1—C21.428 (12)C20—C211.339 (16)
C2—C31.342 (10)C20—H200.9300
C3—C41.437 (10)C21—C221.389 (15)
C5—C61.323 (13)C21—H210.9300
C5—C101.377 (11)C22—C231.398 (10)
C6—C71.405 (16)C22—H220.9300
C6—H60.9300C24—C291.359 (10)
C7—C81.303 (18)C24—C251.389 (10)
C8—C91.433 (17)C24—H240.9300
C8—H80.9300C25—C261.352 (12)
C9—C101.389 (13)C25—H250.9300
C9—H90.9300C26—C271.352 (12)
C10—C111.462 (12)C26—H260.9300
C11—H11A0.9700C27—C281.373 (12)
C11—H11B0.9700C27—H270.9300
C12—C131.369 (9)C28—C291.400 (10)
C12—C171.379 (9)C28—H280.9300
S1—Ni1—S1i180.00 (11)C14—C13—H13119.4
S1—Ni1—S2i87.77 (7)C12—C13—H13119.4
S1i—Ni1—S2i92.23 (7)C13—C14—C15120.7 (7)
S1—Ni1—S292.23 (7)C13—C14—H14119.7
S1i—Ni1—S287.77 (7)C15—C14—H14119.7
S2i—Ni1—S2180.0C14—C15—C16119.2 (7)
C23—P1—C17109.0 (3)C14—C15—H15120.4
C23—P1—C29110.8 (4)C16—C15—H15120.4
C17—P1—C29110.1 (3)C17—C16—C15120.1 (7)
C23—P1—C11110.3 (4)C17—C16—H16119.9
C17—P1—C11108.4 (3)C15—C16—H16119.9
C29—P1—C11108.3 (4)C12—C17—C16119.4 (6)
C2—S1—Ni1103.2 (3)C12—C17—P1120.6 (5)
C3—S2—Ni1102.7 (2)C16—C17—P1119.9 (5)
N1—C1—C2179.0 (10)C23—C18—C19121.8 (8)
C3—C2—C1120.3 (7)C23—C18—H18119.1
C3—C2—S1121.0 (6)C19—C18—H18119.1
C1—C2—S1118.8 (6)C18—C19—C20117.8 (11)
C2—C3—C4120.8 (7)C18—C19—H19121.1
C2—C3—S2120.9 (5)C20—C19—H19121.1
C4—C3—S2118.2 (6)C21—C20—C19120.9 (11)
N2—C4—C3178.5 (12)C21—C20—H20119.6
C6—C5—F1116.3 (8)C19—C20—H20119.6
C6—C5—C10126.8 (9)C20—C21—C22122.2 (9)
F1—C5—C10116.9 (9)C20—C21—H21118.9
C5—C6—C7114.8 (11)C22—C21—H21118.9
C5—C6—H6122.6C21—C22—C23117.3 (9)
C7—C6—H6122.6C21—C22—H22121.3
C8—C7—C6125.5 (13)C23—C22—H22121.3
C8—C7—Br1118.4 (12)C18—C23—C22119.9 (8)
C6—C7—Br1116.1 (13)C18—C23—P1118.9 (6)
C7—C8—C9116.3 (11)C22—C23—P1121.1 (7)
C7—C8—H8121.9C29—C24—C25119.4 (7)
C9—C8—H8121.9C29—C24—H24120.3
C10—C9—C8121.8 (11)C25—C24—H24120.3
C10—C9—H9119.1C26—C25—C24120.9 (8)
C8—C9—H9119.1C26—C25—H25119.5
C5—C10—C9114.7 (10)C24—C25—H25119.5
C5—C10—C11121.5 (8)C27—C26—C25120.1 (8)
C9—C10—C11123.8 (9)C27—C26—H26119.9
C10—C11—P1113.5 (5)C25—C26—H26119.9
C10—C11—H11A108.9C26—C27—C28120.5 (8)
P1—C11—H11A108.9C26—C27—H27119.7
C10—C11—H11B108.9C28—C27—H27119.7
P1—C11—H11B108.9C27—C28—C29119.5 (8)
H11A—C11—H11B107.7C27—C28—H28120.3
C13—C12—C17119.5 (7)C29—C28—H28120.3
C13—C12—H12120.2C24—C29—C28119.4 (7)
C17—C12—H12120.2C24—C29—P1121.3 (5)
C14—C13—C12121.1 (7)C28—C29—P1119.0 (6)
S1i—Ni1—S1—C2117 (100)C14—C15—C16—C170.6 (11)
S2i—Ni1—S1—C2179.3 (2)C13—C12—C17—C160.3 (11)
S2—Ni1—S1—C20.7 (2)C13—C12—C17—P1175.2 (6)
S1—Ni1—S2—C30.8 (2)C15—C16—C17—C121.0 (11)
S1i—Ni1—S2—C3179.2 (2)C15—C16—C17—P1175.9 (6)
S2i—Ni1—S2—C352 (31)C23—P1—C17—C12161.9 (5)
N1—C1—C2—C3138 (69)C29—P1—C17—C1240.2 (7)
N1—C1—C2—S143 (69)C11—P1—C17—C1278.0 (6)
Ni1—S1—C2—C30.3 (6)C23—P1—C17—C1623.2 (7)
Ni1—S1—C2—C1179.8 (6)C29—P1—C17—C16144.9 (6)
C1—C2—C3—C41.4 (11)C11—P1—C17—C1696.9 (6)
S1—C2—C3—C4178.5 (6)C23—C18—C19—C200.9 (15)
C1—C2—C3—S2179.5 (6)C18—C19—C20—C211.2 (17)
S1—C2—C3—S20.4 (8)C19—C20—C21—C220.3 (18)
Ni1—S2—C3—C20.8 (6)C20—C21—C22—C231.0 (14)
Ni1—S2—C3—C4179.0 (5)C19—C18—C23—C220.4 (14)
C2—C3—C4—N230 (40)C19—C18—C23—P1176.1 (8)
S2—C3—C4—N2152 (39)C21—C22—C23—C181.3 (12)
F1—C5—C6—C7179.1 (8)C21—C22—C23—P1175.1 (7)
C10—C5—C6—C71.4 (14)C17—P1—C23—C1854.2 (7)
C5—C6—C7—C83.2 (16)C29—P1—C23—C1867.1 (8)
C5—C6—C7—Br1177.8 (7)C11—P1—C23—C18173.1 (7)
C6—C7—C8—C94.9 (18)C17—P1—C23—C22122.2 (6)
Br1—C7—C8—C9176.1 (7)C29—P1—C23—C22116.5 (6)
C7—C8—C9—C102.3 (16)C11—P1—C23—C223.3 (7)
C6—C5—C10—C93.5 (13)C29—C24—C25—C260.6 (14)
F1—C5—C10—C9177.0 (7)C24—C25—C26—C270.6 (16)
C6—C5—C10—C11175.8 (9)C25—C26—C27—C280.2 (18)
F1—C5—C10—C113.7 (11)C26—C27—C28—C292.2 (17)
C8—C9—C10—C51.5 (13)C25—C24—C29—C282.5 (13)
C8—C9—C10—C11177.8 (8)C25—C24—C29—P1176.8 (7)
C5—C10—C11—P188.1 (8)C27—C28—C29—C243.4 (15)
C9—C10—C11—P191.2 (9)C27—C28—C29—P1177.8 (8)
C23—P1—C11—C10167.2 (5)C23—P1—C29—C2492.6 (7)
C17—P1—C11—C1048.0 (7)C17—P1—C29—C2428.0 (8)
C29—P1—C11—C1071.4 (6)C11—P1—C29—C24146.3 (7)
C17—C12—C13—C140.7 (12)C23—P1—C29—C2881.7 (8)
C12—C13—C14—C151.1 (13)C17—P1—C29—C28157.7 (7)
C13—C14—C15—C160.5 (12)C11—P1—C29—C2839.4 (9)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···N2ii0.932.583.400 (11)148
C24—H24···N1iii0.932.613.460 (13)152
C28—H28···S2iv0.932.833.706 (9)157
Symmetry codes: (ii) x, y+1/2, z3/2; (iii) x, y+1/2, z1/2; (iv) x+1, y+1/2, z1/2.
 

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