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Acta Cryst. (2007). E63, m2858
https://doi.org/10.1107/S160053680705297X
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Bis[(3-fluoro­benz­yl)triphenyl­phospho­nium] bis­(1,2-dicyano­ethene-1,2-dithiol­ato-κ2S,S′)nickel(II)

Q.-B. Liao, M.-G. Liu and C.-L. Ni
In the title salt, (C25H21FP)2[Ni(C4N2S2)2], the NiII ion lies on an inversion centre and the [Ni(mnt)2]2− anion (mnt is maleonitrile­dithiol­ate) exhibits a square-planar coordination geometry. The (3-fluoro­benz­yl)triphenyl­phospho­nium cation adopts a conformation in which the four aromatic rings are twisted with respect to the plane including the P atom and the two C atoms linking it to the 3-fluoro­benzyl ring. A weak C—H...N hydrogen bond and a C—H...π inter­action stabilize the crystal structure.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705297X/sj2383sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705297X/sj2383Isup2.hkl
Contains datablock I

CCDC reference: 667250

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.034
  • wR factor = 0.106
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found




Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          4
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C20    -   C21     ..       5.19 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   S1      ..       5.94 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
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     ...       1.43 Ang.


Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1         (3)       2.79
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1


   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check
Comment top

The unusual physical properties of complexes containing the Ni(mnt)22- anion are partly attributed to intermolecular interactions between Ni(mnt)22- anions and a variety of multifunctional cations (Robertson & Cronin, 2002; Ni et al., 2004). In recent years, we have introduced other substituted benzyltriphenylphosphinium cations into the Ni(mnt)22- system and obtained some Ni(mnt)22--based molecular solids (Ni et al., 2005; Yang & Ni, 2006; Liu & Ni, 2006; Zhou et al., 2007). As shown in Fig.1, the title compound is isostructural with (BzTPP)2+ [Ni(mnt)2]2- Zhou et al., 2007). The asymmetric unit of (I) consists of one [mFBzTPP]+ cation and one-half of a Ni(mnt)22- anion as the Ni atom lies on an inversion centre. The nickel(II) ion is coordinated by four S atoms from two mnt2- ligands and the Ni(mnt)22- anion is in a square planar configuration. The two N atoms of the CN groups deviate from the Ni1/S1/S2 plane by 0.392 (2) Å for N1 and 0.451 (2) Å for N2.

The [mFBzTPP]+ cation adopts a conformation where four phenyl rings are twisted with respect to the P1—C11—C10 plane with dihedral angles of 91.2 (2) for the C5/C6/C7/C8/C9/C10 ring, 81.7 (2)° for the C12/C13/C14/C15/C16/C17 ring, 20.6 (2)° for the C18/C19/C20/C21/C22/C23 ring, and 86.9 (2)° for the C24/C25/C26/C27/C28/C29 ring. The deviation of the F atom from the C5/C6/C7/C8/C9/C10 phenyl ring plane is -0.041 (2) Å.

The crystal structure is stabilized by a C9—H9···N1 hydrogen bond, Table 1, and a C13—H13···π interaction with the C24i···C29i ring [symmetry code: (i) 1 - x, -y, 1 - z]. The distance between C13 and the centroid of the C24i···C29i ring is 3.705 (2) Å, Fig 2.

Related literature top

For details of other [Ni(mnt)2]2- complexes, see: Robertson & Cronin (2002); Ni et al. (2004, 2005); Liu & Ni (2006). For closely related [Ni(mnt)2]2- complexes with square-planar geometry and a substituted triphenylphosphinium counterion, see: Yang & Ni (2006); Zhou et al. (2007).

Experimental top

The title compound was prepared by the direct reaction of NiCl2.6H2O, Na2mnt and (mFBzTPP)Br in methanol. Red block-shaped single crystals were obtained by slow evaporation of a CH3CN solution at room temperature over two weeks.

Refinement top

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso = 1.2Ueq(C) for aromatic and 0.97 Å, Uiso = 1.2Ueq(C) for CH2 atoms.

Structure description top

The unusual physical properties of complexes containing the Ni(mnt)22- anion are partly attributed to intermolecular interactions between Ni(mnt)22- anions and a variety of multifunctional cations (Robertson & Cronin, 2002; Ni et al., 2004). In recent years, we have introduced other substituted benzyltriphenylphosphinium cations into the Ni(mnt)22- system and obtained some Ni(mnt)22--based molecular solids (Ni et al., 2005; Yang & Ni, 2006; Liu & Ni, 2006; Zhou et al., 2007). As shown in Fig.1, the title compound is isostructural with (BzTPP)2+ [Ni(mnt)2]2- Zhou et al., 2007). The asymmetric unit of (I) consists of one [mFBzTPP]+ cation and one-half of a Ni(mnt)22- anion as the Ni atom lies on an inversion centre. The nickel(II) ion is coordinated by four S atoms from two mnt2- ligands and the Ni(mnt)22- anion is in a square planar configuration. The two N atoms of the CN groups deviate from the Ni1/S1/S2 plane by 0.392 (2) Å for N1 and 0.451 (2) Å for N2.

The [mFBzTPP]+ cation adopts a conformation where four phenyl rings are twisted with respect to the P1—C11—C10 plane with dihedral angles of 91.2 (2) for the C5/C6/C7/C8/C9/C10 ring, 81.7 (2)° for the C12/C13/C14/C15/C16/C17 ring, 20.6 (2)° for the C18/C19/C20/C21/C22/C23 ring, and 86.9 (2)° for the C24/C25/C26/C27/C28/C29 ring. The deviation of the F atom from the C5/C6/C7/C8/C9/C10 phenyl ring plane is -0.041 (2) Å.

The crystal structure is stabilized by a C9—H9···N1 hydrogen bond, Table 1, and a C13—H13···π interaction with the C24i···C29i ring [symmetry code: (i) 1 - x, -y, 1 - z]. The distance between C13 and the centroid of the C24i···C29i ring is 3.705 (2) Å, Fig 2.

For details of other [Ni(mnt)2]2- complexes, see: Robertson & Cronin (2002); Ni et al. (2004, 2005); Liu & Ni (2006). For closely related [Ni(mnt)2]2- complexes with square-planar geometry and a substituted triphenylphosphinium counterion, see: Yang & Ni (2006); Zhou et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Bruker, 2000; molecular graphics: SHELXTL (Bruker, 2000; software used to prepare material for publication: SHELXTL (Bruker, 2000.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The C—H···π hydrogen bond between cations.
Bis[(3-fluorobenzyl)triphenylphosphonium] bis(1,2-dicyanoethene-1,2-dithiolato-κ2S,S')nickel(II) top
Crystal data top
(C25H21FP)2[Ni(C4N2S2)2]F(000) = 1116
Mr = 1081.85Dx = 1.394 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6299 reflections
a = 9.429 (1) Åθ = 2.3–27.3°
b = 14.625 (1) ŵ = 0.65 mm−1
c = 18.912 (1) ÅT = 291 K
β = 98.73 (1)°Block, red
V = 2577.7 (4) Å30.51 × 0.41 × 0.30 mm
Z = 2
Data collection top
Bruker SMART APEX CCD
diffractometer		5065 independent reflections
Radiation source: fine-focus sealed tube4084 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −11→11
Tmin = 0.730, Tmax = 0.825k = −13→18
14690 measured reflectionsl = −23→20
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.07P)2]
where P = (Fo2 + 2Fc2)/3
5065 reflections(Δ/σ)max = 0.001
322 parametersΔρmax = 0.61 e Å−3
1 restraintΔρmin = −0.33 e Å−3
Crystal data top
(C25H21FP)2[Ni(C4N2S2)2]V = 2577.7 (4) Å3
Mr = 1081.85Z = 2
Monoclinic, P21/nMo Kα radiation
a = 9.429 (1) ŵ = 0.65 mm−1
b = 14.625 (1) ÅT = 291 K
c = 18.912 (1) Å0.51 × 0.41 × 0.30 mm
β = 98.73 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer		5065 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		4084 reflections with I > 2σ(I)
Tmin = 0.730, Tmax = 0.825Rint = 0.019
14690 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0341 restraint
wR(F2) = 0.106H-atom parameters constrained
S = 1.01Δρmax = 0.61 e Å−3
5065 reflectionsΔρmin = −0.33 e Å−3
322 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ni10.50000.50000.00000.04385 (12)
P10.78361 (5)0.64448 (4)0.83224 (3)0.04648 (15)
S10.67420 (5)0.40712 (4)0.03967 (3)0.05430 (16)
S20.59246 (6)0.59631 (4)0.08152 (3)0.05951 (17)
N10.8175 (2)0.17840 (17)−0.00067 (13)0.0870 (7)
N20.5246 (2)0.83161 (15)0.14742 (11)0.0734 (6)
F10.4030 (2)0.92911 (15)0.89371 (15)0.1436 (9)
C10.7381 (2)0.23857 (17)−0.00796 (11)0.0603 (6)
C20.6407 (2)0.31418 (15)−0.01694 (10)0.0497 (5)
C30.4754 (2)0.68785 (14)0.06882 (10)0.0482 (5)
C40.5041 (2)0.76731 (16)0.11311 (11)0.0558 (5)
C50.5660 (2)0.80705 (17)0.90768 (14)0.0678 (6)
H50.49170.76680.89160.081*
C60.5389 (3)0.89860 (19)0.91348 (16)0.0789 (7)
C70.6417 (3)0.9608 (2)0.93787 (14)0.0791 (7)
H70.61961.02230.94250.095*
C80.7797 (3)0.9290 (2)0.95544 (15)0.0874 (8)
H80.85310.97000.97140.105*
C90.8112 (3)0.8374 (2)0.94982 (13)0.0761 (7)
H90.90520.81720.96220.091*
C100.7038 (2)0.77539 (16)0.92591 (10)0.0562 (5)
C110.7404 (2)0.67552 (16)0.91959 (11)0.0605 (6)
H11A0.65970.63890.92920.073*
H11B0.82170.66090.95570.073*
C120.8433 (2)0.80663 (14)0.76758 (12)0.0565 (5)
H120.74500.81150.75260.068*
C130.9331 (3)0.87451 (16)0.75220 (14)0.0664 (6)
H130.89570.92570.72680.080*
C141.0780 (3)0.86767 (17)0.77401 (14)0.0690 (6)
H141.13870.91390.76290.083*
C151.1338 (2)0.79326 (17)0.81201 (13)0.0656 (6)
H151.23220.78930.82700.079*
C161.0452 (2)0.72424 (15)0.82816 (11)0.0558 (5)
H161.08330.67360.85410.067*
C170.89864 (19)0.73057 (13)0.80547 (10)0.0452 (4)
C180.9536 (3)0.51284 (16)0.78456 (14)0.0657 (6)
H180.95380.55070.74510.079*
C191.0288 (3)0.43144 (18)0.78898 (18)0.0805 (8)
H191.08100.41500.75300.097*
C201.0259 (3)0.37512 (19)0.8466 (2)0.0928 (10)
H201.07700.32050.85000.111*
C210.9487 (3)0.3988 (2)0.89900 (19)0.0920 (10)
H210.94580.35940.93730.110*
C220.8753 (3)0.47950 (18)0.89629 (15)0.0751 (7)
H220.82380.49520.93270.090*
C230.8783 (2)0.53805 (15)0.83866 (11)0.0524 (5)
C240.6370 (2)0.63541 (16)0.69513 (11)0.0569 (5)
H240.72600.64470.68080.068*
C250.5170 (2)0.62204 (17)0.64484 (13)0.0674 (6)
H250.52610.62090.59660.081*
C260.3853 (3)0.61046 (16)0.66474 (15)0.0694 (6)
H260.30480.60290.63020.083*
C270.3719 (2)0.60994 (15)0.73614 (15)0.0655 (6)
H270.28190.60220.74970.079*
C280.4904 (2)0.62075 (14)0.78769 (12)0.0549 (5)
H280.48080.61860.83590.066*
C290.6246 (2)0.63497 (13)0.76764 (10)0.0464 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0420 (2)0.0564 (2)0.03404 (19)0.00268 (15)0.00871 (14)−0.00133 (14)
P10.0459 (3)0.0522 (3)0.0420 (3)−0.0005 (2)0.0087 (2)0.0077 (2)
S10.0499 (3)0.0656 (4)0.0452 (3)0.0081 (2)0.0001 (2)−0.0077 (2)
S20.0557 (3)0.0685 (4)0.0502 (3)0.0104 (3)−0.0050 (2)−0.0119 (3)
N10.0793 (15)0.0901 (16)0.0855 (16)0.0270 (13)−0.0068 (12)−0.0113 (13)
N20.0780 (14)0.0693 (13)0.0709 (13)−0.0023 (11)0.0047 (11)−0.0146 (11)
F10.0827 (12)0.1171 (15)0.228 (3)0.0133 (11)0.0136 (13)−0.0575 (16)
C10.0591 (13)0.0697 (15)0.0502 (12)0.0076 (12)0.0019 (10)−0.0074 (11)
C20.0494 (11)0.0578 (12)0.0429 (11)0.0046 (9)0.0102 (9)−0.0015 (9)
C30.0485 (11)0.0552 (12)0.0416 (10)0.0024 (9)0.0091 (8)−0.0023 (9)
C40.0536 (12)0.0650 (14)0.0487 (12)0.0022 (10)0.0070 (9)−0.0034 (11)
C50.0548 (13)0.0735 (16)0.0790 (16)−0.0137 (12)0.0224 (11)−0.0236 (13)
C60.0685 (14)0.0797 (18)0.0902 (19)−0.0038 (13)0.0178 (13)−0.0230 (15)
C70.092 (2)0.0690 (16)0.0770 (17)−0.0121 (15)0.0159 (15)−0.0146 (14)
C80.090 (2)0.083 (2)0.085 (2)−0.0294 (16)0.0008 (15)−0.0191 (15)
C90.0634 (15)0.095 (2)0.0654 (15)−0.0096 (14)−0.0037 (12)−0.0114 (14)
C100.0635 (13)0.0701 (14)0.0366 (10)−0.0092 (11)0.0128 (9)−0.0052 (9)
C110.0682 (14)0.0716 (15)0.0426 (11)−0.0004 (11)0.0109 (10)0.0064 (10)
C120.0474 (11)0.0563 (13)0.0661 (14)0.0078 (10)0.0091 (10)0.0107 (11)
C130.0706 (15)0.0461 (12)0.0841 (17)0.0029 (11)0.0171 (13)0.0161 (12)
C140.0657 (15)0.0563 (14)0.0871 (18)−0.0149 (11)0.0183 (13)0.0013 (12)
C150.0478 (12)0.0661 (15)0.0803 (16)−0.0101 (11)0.0009 (11)−0.0007 (12)
C160.0505 (11)0.0558 (12)0.0569 (13)−0.0029 (10)−0.0050 (9)0.0054 (10)
C170.0453 (10)0.0470 (11)0.0435 (10)−0.0011 (8)0.0071 (8)0.0033 (8)
C180.0644 (14)0.0566 (14)0.0774 (16)0.0039 (11)0.0154 (12)0.0078 (11)
C190.0639 (15)0.0595 (15)0.119 (2)0.0050 (12)0.0168 (15)−0.0017 (16)
C200.0581 (15)0.0516 (15)0.159 (3)0.0008 (12)−0.0140 (18)0.0178 (18)
C210.0782 (19)0.0719 (19)0.121 (3)−0.0015 (15)−0.0026 (18)0.0453 (18)
C220.0697 (16)0.0733 (16)0.0800 (17)0.0006 (13)0.0038 (13)0.0307 (14)
C230.0460 (11)0.0494 (11)0.0610 (13)−0.0031 (9)0.0054 (9)0.0107 (10)
C240.0511 (12)0.0700 (14)0.0506 (12)−0.0007 (10)0.0106 (9)0.0038 (10)
C250.0680 (15)0.0775 (16)0.0537 (13)0.0012 (12)−0.0007 (11)0.0026 (11)
C260.0578 (14)0.0640 (15)0.0807 (18)0.0016 (11)−0.0076 (12)−0.0066 (13)
C270.0425 (12)0.0584 (14)0.0969 (19)−0.0034 (10)0.0147 (12)−0.0143 (13)
C280.0527 (12)0.0534 (12)0.0623 (13)−0.0030 (10)0.0212 (10)−0.0055 (10)
C290.0434 (10)0.0472 (11)0.0494 (11)0.0012 (8)0.0097 (8)0.0006 (9)
Geometric parameters (Å, º) top
Ni1—S2i2.1709 (5)C12—H120.9300
Ni1—S22.1709 (5)C13—C141.370 (3)
Ni1—S1i2.1753 (5)C13—H130.9300
Ni1—S12.1753 (5)C14—C151.365 (3)
P1—C171.7846 (19)C14—H140.9300
P1—C231.790 (2)C15—C161.374 (3)
P1—C291.790 (2)C15—H150.9300
P1—C111.818 (2)C16—C171.386 (2)
S1—C21.729 (2)C16—H160.9300
S2—C31.729 (2)C18—C231.381 (3)
N1—C11.150 (3)C18—C191.381 (3)
N2—C41.142 (3)C18—H180.9300
F1—C61.355 (3)C19—C201.370 (4)
C1—C21.431 (3)C19—H190.9300
C2—C3i1.354 (3)C20—C211.360 (5)
C3—C2i1.354 (3)C20—H200.9300
C3—C41.434 (3)C21—C221.364 (4)
C5—C61.371 (4)C21—H210.9300
C5—C101.374 (3)C22—C231.390 (3)
C5—H50.9300C22—H220.9300
C6—C71.358 (4)C24—C251.377 (3)
C7—C81.374 (4)C24—C291.394 (3)
C7—H70.9300C24—H240.9300
C8—C91.380 (4)C25—C261.362 (3)
C8—H80.9300C25—H250.9300
C9—C101.383 (3)C26—C271.375 (4)
C9—H90.9300C26—H260.9300
C10—C111.510 (3)C27—C281.376 (3)
C11—H11A0.9700C27—H270.9300
C11—H11B0.9700C28—C291.390 (3)
C12—C131.365 (3)C28—H280.9300
C12—C171.382 (3)
S2i—Ni1—S2180.00 (2)C12—C13—H13119.8
S2i—Ni1—S1i87.67 (2)C14—C13—H13119.8
S2—Ni1—S1i92.33 (2)C15—C14—C13120.2 (2)
S2i—Ni1—S192.33 (2)C15—C14—H14119.9
S2—Ni1—S187.67 (2)C13—C14—H14119.9
S1i—Ni1—S1180.00 (3)C14—C15—C16120.3 (2)
C17—P1—C23108.32 (9)C14—C15—H15119.9
C17—P1—C29110.09 (9)C16—C15—H15119.9
C23—P1—C29109.66 (10)C15—C16—C17119.6 (2)
C17—P1—C11108.13 (10)C15—C16—H16120.2
C23—P1—C11109.50 (10)C17—C16—H16120.2
C29—P1—C11111.08 (10)C12—C17—C16119.64 (19)
C2—S1—Ni1102.69 (7)C12—C17—P1121.12 (15)
C3—S2—Ni1102.98 (7)C16—C17—P1119.03 (15)
N1—C1—C2179.3 (3)C23—C18—C19120.1 (2)
C3i—C2—C1120.16 (19)C23—C18—H18119.9
C3i—C2—S1121.15 (16)C19—C18—H18119.9
C1—C2—S1118.69 (15)C20—C19—C18119.6 (3)
C2i—C3—C4120.07 (18)C20—C19—H19120.2
C2i—C3—S2120.82 (15)C18—C19—H19120.2
C4—C3—S2119.10 (15)C21—C20—C19120.2 (3)
N2—C4—C3178.5 (3)C21—C20—H20119.9
C6—C5—C10119.3 (2)C19—C20—H20119.9
C6—C5—H5120.3C20—C21—C22121.2 (3)
C10—C5—H5120.3C20—C21—H21119.4
F1—C6—C7118.0 (3)C22—C21—H21119.4
F1—C6—C5118.6 (2)C21—C22—C23119.4 (3)
C7—C6—C5123.4 (3)C21—C22—H22120.3
C6—C7—C8117.1 (3)C23—C22—H22120.3
C6—C7—H7121.4C18—C23—C22119.4 (2)
C8—C7—H7121.4C18—C23—P1119.30 (16)
C7—C8—C9121.1 (3)C22—C23—P1121.32 (19)
C7—C8—H8119.4C25—C24—C29119.7 (2)
C9—C8—H8119.4C25—C24—H24120.1
C8—C9—C10120.4 (3)C29—C24—H24120.1
C8—C9—H9119.8C26—C25—C24121.0 (2)
C10—C9—H9119.8C26—C25—H25119.5
C5—C10—C9118.6 (2)C24—C25—H25119.5
C5—C10—C11121.7 (2)C25—C26—C27119.7 (2)
C9—C10—C11119.7 (2)C25—C26—H26120.1
C10—C11—P1113.51 (14)C27—C26—H26120.1
C10—C11—H11A108.9C26—C27—C28120.6 (2)
P1—C11—H11A108.9C26—C27—H27119.7
C10—C11—H11B108.9C28—C27—H27119.7
P1—C11—H11B108.9C27—C28—C29119.9 (2)
H11A—C11—H11B107.7C27—C28—H28120.0
C13—C12—C17119.88 (19)C29—C28—H28120.0
C13—C12—H12120.1C28—C29—C24119.01 (19)
C17—C12—H12120.1C28—C29—P1121.88 (16)
C12—C13—C14120.4 (2)C24—C29—P1118.96 (15)
Symmetry code: (i) −x+1, −y+1, −z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···N1ii0.932.613.495 (3)160
C13—H13···Cgiii0.93Missing3.705 (2)Missing
Symmetry codes: (ii) −x+2, −y+1, −z+1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula(C25H21FP)2[Ni(C4N2S2)2]
Mr1081.85
Crystal system, space groupMonoclinic, P21/n
Temperature (K)291
a, b, c (Å)9.429 (1), 14.625 (1), 18.912 (1)
β (°) 98.73 (1)
V (Å3)2577.7 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.65
Crystal size (mm)0.51 × 0.41 × 0.30
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.730, 0.825
No. of measured, independent and
observed [I > 2σ(I)] reflections		14690, 5065, 4084
Rint0.019
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.106, 1.01
No. of reflections5065
No. of parameters322
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.61, −0.33

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Bruker, 2000), SHELXTL (Bruker, 2000.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9···N1i0.9302.6103.495 (3)160
C13—H13···Cgii0.93Missing3.705 (2)Missing
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1.
 

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