[1,2-Bis­(di­phenyl­phosphino)­ethane](2,3-quinoxalinedi­thiol­ato)­nickel(II)

A novel nickel(II) mixed-ligand complex, [Ni(C₈H₄N₂S₂)(C₂₆H₂₄P₂)], containing a di­thiol­ate and a phosphine derivative as ligands, was prepared from the reaction of Ni(dppe)Cl₂ [dppe is 1,2-bis(di­phenyl­phosphino)­ethane] with H₂qdt (qdt is 2,3-quinoxalinedi­thiol­ate), using Et₃N as a base. The crystal structure of this compound shows a square-planar nickel environment. In the crystal structure, weak C—H...S interactions are the principal intermolecular forces, mediating the formation of ribbons along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• R factor = 0.055
• wR factor = 0.156
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro .          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT480_ALERT_4_C Long H...A H-Bond Reported H20    ..  S2      ..       2.89 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               5998
           Count of symmetry unique reflns         3386
           Completeness (_total/calc)            177.14%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2612
           Fraction of Friedel pairs measured     0.771
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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.

[1,2-bis(diphenylphosphino)ethane](2,3-quionoxalinedithiolato)nickel

Crystal data

[Ni(C8H4N2S2)(C26H24P2)]	F(000) = 1344
Mr = 649.35	Dx = 1.405 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1624 reflections
a = 11.427 (1) Å	θ = 2.4–16.2°
b = 12.947 (1) Å	µ = 0.90 mm^−1
c = 20.752 (2) Å	T = 293 K
V = 3070.2 (5) Å^3	Block, red
Z = 4	0.32 × 0.25 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	5998 independent reflections
Radiation source: sealed tube	5513 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→14
Tmin = 0.76, Tmax = 0.86	k = −15→13
16591 measured reflections	l = −24→25

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.156	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.1P)^2 + 1.99P] where P = (Fo^2 + 2Fc^2)/3
5998 reflections	(Δ/σ)max < 0.001
370 parameters	Δρmax = 0.70 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni1	0.18932 (6)	0.96111 (5)	0.15855 (3)	0.03942 (18)
P1	0.03332 (12)	0.92186 (11)	0.21376 (6)	0.0406 (3)
P2	0.22332 (12)	0.79560 (10)	0.15480 (6)	0.0415 (3)
S1	0.36090 (12)	0.98919 (10)	0.11786 (6)	0.0426 (3)
S2	0.14561 (12)	1.12391 (10)	0.15555 (6)	0.0437 (3)
N1	0.4574 (4)	1.1603 (3)	0.0734 (2)	0.0489 (11)
N2	0.2628 (5)	1.2811 (3)	0.1053 (2)	0.0518 (11)
C1	0.3632 (5)	1.1202 (4)	0.1010 (2)	0.0401 (11)
C2	0.4547 (6)	1.2611 (4)	0.0609 (2)	0.0499 (13)
C3	0.5560 (6)	1.3103 (5)	0.0318 (3)	0.0598 (16)
H3	0.6232	1.2721	0.0233	0.072*
C4	0.5518 (6)	1.4117 (4)	0.0172 (3)	0.0501 (13)
H4	0.6159	1.4423	−0.0028	0.060*
C5	0.4553 (5)	1.4710 (4)	0.0309 (2)	0.0502 (13)
H5	0.4560	1.5410	0.0210	0.060*
C6	0.3575 (6)	1.4284 (4)	0.0592 (3)	0.0502 (13)
H6	0.2924	1.4694	0.0674	0.060*
C7	0.3561 (6)	1.3224 (4)	0.0757 (3)	0.0496 (13)
C8	0.2633 (4)	1.1820 (4)	0.1173 (2)	0.0398 (11)
C9	−0.1080 (5)	0.9803 (4)	0.1989 (3)	0.0490 (13)
C10	−0.1296 (5)	1.0369 (4)	0.1446 (3)	0.0492 (12)
H10	−0.0690	1.0502	0.1159	0.059*
C11	−0.2392 (5)	1.0743 (5)	0.1318 (3)	0.0491 (13)
H11	−0.2527	1.1114	0.0942	0.059*
C12	−0.3297 (5)	1.0573 (4)	0.1745 (3)	0.0491 (13)
H12	−0.4037	1.0844	0.1664	0.059*
C13	−0.3095 (5)	1.0000 (5)	0.2286 (3)	0.0491 (12)
H13	−0.3706	0.9867	0.2570	0.059*
C14	−0.2016 (5)	0.9626 (4)	0.2413 (3)	0.0493 (12)
H14	−0.1892	0.9244	0.2786	0.059*
C15	0.0663 (5)	0.9368 (4)	0.2987 (3)	0.0496 (13)
C16	0.1440 (5)	1.0131 (4)	0.3184 (3)	0.0500 (13)
H16	0.1765	1.0571	0.2879	0.060*
C17	0.1738 (5)	1.0248 (4)	0.3823 (3)	0.0504 (13)
H17	0.2269	1.0758	0.3942	0.060*
C18	0.1259 (5)	0.9618 (4)	0.4287 (3)	0.0503 (13)
H18	0.1494	0.9670	0.4715	0.060*
C19	0.0416 (6)	0.8902 (4)	0.4104 (3)	0.0505 (13)
H19	0.0033	0.8512	0.4416	0.061*
C20	0.0144 (5)	0.8766 (4)	0.3458 (3)	0.0504 (12)
H20	−0.0395	0.8262	0.3340	0.061*
C21	0.2003 (6)	0.7421 (4)	0.0734 (3)	0.0499 (13)
C22	0.1256 (6)	0.6631 (4)	0.0633 (3)	0.0504 (13)
H22	0.0851	0.6352	0.0981	0.060*
C23	0.1072 (5)	0.6215 (4)	0.0008 (3)	0.0498 (13)
H23	0.0556	0.5671	−0.0061	0.060*
C24	0.1664 (5)	0.6633 (4)	−0.0468 (3)	0.0504 (14)
H24	0.1440	0.6474	−0.0887	0.061*
C25	0.2602 (6)	0.7297 (4)	−0.0381 (3)	0.0504 (13)
H25	0.3102	0.7454	−0.0720	0.061*
C26	0.2787 (6)	0.7744 (4)	0.0261 (3)	0.0503 (13)
H26	0.3385	0.8211	0.0345	0.060*
C27	0.3674 (5)	0.7523 (4)	0.1812 (2)	0.0471 (12)
C28	0.4250 (5)	0.6731 (5)	0.1524 (3)	0.0596 (15)
H28	0.3921	0.6407	0.1167	0.072*
C29	0.5315 (5)	0.6402 (4)	0.1753 (2)	0.0503 (13)
H29	0.5706	0.5863	0.1549	0.060*
C30	0.5806 (6)	0.6874 (4)	0.2288 (3)	0.0502 (13)
H30	0.6522	0.6651	0.2450	0.060*
C31	0.5216 (5)	0.7682 (4)	0.2577 (3)	0.0502 (13)
H31	0.5544	0.8018	0.2930	0.060*
C32	0.4160 (6)	0.7986 (4)	0.2348 (3)	0.0500 (13)
H32	0.3757	0.8515	0.2555	0.060*
C33	0.0045 (5)	0.7841 (4)	0.2054 (3)	0.0505 (13)
H33A	−0.0461	0.7606	0.2400	0.061*
H33B	−0.0340	0.7704	0.1647	0.061*
C34	0.1228 (5)	0.7271 (4)	0.2083 (3)	0.0520 (13)
H34A	0.1136	0.6561	0.1943	0.062*
H34B	0.1528	0.7271	0.2520	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0485 (3)	0.0356 (3)	0.0342 (3)	−0.0009 (3)	−0.0008 (3)	−0.0015 (3)
P1	0.0498 (7)	0.0378 (7)	0.0343 (6)	−0.0034 (6)	−0.0001 (5)	−0.0022 (5)
P2	0.0521 (7)	0.0363 (7)	0.0360 (6)	−0.0012 (5)	−0.0033 (6)	−0.0014 (5)
S1	0.0516 (7)	0.0358 (6)	0.0404 (6)	0.0004 (6)	0.0016 (6)	−0.0013 (5)
S2	0.0521 (7)	0.0381 (6)	0.0411 (6)	0.0015 (5)	0.0019 (6)	−0.0015 (6)
N1	0.063 (3)	0.041 (2)	0.043 (2)	−0.008 (2)	0.006 (2)	0.0021 (19)
N2	0.067 (3)	0.040 (3)	0.049 (3)	−0.002 (2)	0.000 (2)	0.0007 (19)
C1	0.054 (3)	0.033 (2)	0.033 (2)	−0.002 (2)	−0.005 (2)	−0.003 (2)
C2	0.069 (4)	0.048 (3)	0.033 (3)	−0.011 (3)	0.005 (2)	−0.001 (2)
C3	0.083 (4)	0.053 (4)	0.043 (3)	−0.009 (3)	0.008 (3)	0.002 (3)
C4	0.068 (4)	0.039 (3)	0.043 (3)	−0.006 (3)	−0.004 (3)	0.002 (2)
C5	0.068 (4)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C6	0.068 (3)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.004 (3)	0.002 (2)
C7	0.067 (4)	0.038 (3)	0.043 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C8	0.043 (3)	0.045 (3)	0.031 (2)	−0.002 (2)	0.003 (2)	−0.003 (2)
C9	0.043 (3)	0.050 (3)	0.053 (3)	0.002 (2)	0.001 (2)	−0.008 (2)
C10	0.044 (3)	0.051 (3)	0.053 (3)	0.002 (2)	0.001 (2)	−0.008 (3)
C11	0.044 (3)	0.050 (3)	0.053 (3)	0.002 (3)	0.001 (2)	−0.008 (2)
C12	0.044 (3)	0.050 (3)	0.053 (3)	0.002 (2)	0.001 (2)	−0.008 (2)
C13	0.044 (3)	0.050 (3)	0.053 (3)	0.002 (3)	0.001 (2)	−0.008 (2)
C14	0.044 (3)	0.051 (3)	0.053 (3)	0.002 (3)	0.002 (2)	−0.008 (3)
C15	0.067 (4)	0.039 (3)	0.043 (3)	−0.005 (3)	−0.004 (3)	0.002 (2)
C16	0.067 (3)	0.039 (3)	0.043 (3)	−0.005 (3)	−0.004 (3)	0.002 (2)
C17	0.068 (4)	0.040 (3)	0.044 (3)	−0.006 (3)	−0.005 (3)	0.002 (2)
C18	0.068 (4)	0.040 (3)	0.043 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C19	0.069 (4)	0.040 (3)	0.043 (3)	−0.006 (3)	−0.004 (3)	0.002 (2)
C20	0.068 (3)	0.040 (3)	0.043 (3)	−0.006 (3)	−0.004 (3)	0.002 (2)
C21	0.068 (4)	0.038 (3)	0.043 (3)	−0.004 (3)	−0.005 (3)	0.002 (2)
C22	0.068 (4)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.004 (3)	0.001 (2)
C23	0.066 (4)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C24	0.068 (4)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C25	0.069 (4)	0.039 (3)	0.043 (3)	−0.005 (3)	−0.004 (3)	0.002 (2)
C26	0.069 (4)	0.039 (3)	0.043 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C27	0.053 (3)	0.052 (3)	0.036 (3)	0.001 (3)	−0.002 (2)	0.008 (2)
C28	0.056 (3)	0.072 (4)	0.050 (3)	0.014 (3)	−0.003 (3)	0.000 (3)
C29	0.067 (4)	0.039 (3)	0.044 (3)	−0.004 (3)	−0.004 (3)	0.002 (2)
C30	0.067 (3)	0.040 (3)	0.044 (3)	−0.005 (3)	−0.005 (3)	0.003 (2)
C31	0.068 (4)	0.039 (3)	0.044 (3)	−0.005 (3)	−0.005 (3)	0.002 (2)
C32	0.067 (4)	0.039 (3)	0.044 (3)	−0.004 (3)	−0.005 (3)	0.002 (2)
C33	0.053 (3)	0.045 (3)	0.054 (3)	−0.013 (3)	0.006 (3)	0.003 (2)
C34	0.055 (3)	0.039 (3)	0.062 (3)	−0.002 (3)	0.003 (3)	0.006 (3)

Geometric parameters (Å, º)

Ni1—S1	2.1656 (15)	C15—C20	1.384 (8)
Ni1—S2	2.1671 (14)	C15—C16	1.390 (8)
Ni1—P2	2.1791 (14)	C16—C17	1.377 (8)
Ni1—P1	2.1791 (15)	C16—H16	0.9300
P1—C9	1.809 (6)	C17—C18	1.376 (8)
P1—C15	1.812 (5)	C17—H17	0.9300
P1—C33	1.822 (6)	C18—C19	1.389 (8)
P2—C27	1.823 (6)	C18—H18	0.9300
P2—C34	1.827 (6)	C19—C20	1.389 (7)
P2—C21	1.845 (5)	C19—H19	0.9300
S1—C1	1.732 (5)	C20—H20	0.9300
S2—C8	1.734 (5)	C21—C22	1.349 (8)
N1—C1	1.326 (7)	C21—C26	1.393 (8)
N1—C2	1.331 (7)	C22—C23	1.419 (7)
N2—C8	1.307 (7)	C22—H22	0.9300
N2—C7	1.341 (8)	C23—C24	1.313 (8)
C1—C8	1.434 (7)	C23—H23	0.9300
C2—C7	1.412 (9)	C24—C25	1.386 (8)
C2—C3	1.453 (9)	C24—H24	0.9300
C3—C4	1.348 (8)	C25—C26	1.467 (7)
C3—H3	0.9300	C25—H25	0.9300
C4—C5	1.374 (8)	C26—H26	0.9300
C4—H4	0.9300	C27—C28	1.358 (8)
C5—C6	1.376 (8)	C27—C32	1.380 (8)
C5—H5	0.9300	C28—C29	1.374 (8)
C6—C7	1.415 (7)	C28—H28	0.9300
C6—H6	0.9300	C29—C30	1.387 (7)
C9—C10	1.366 (8)	C29—H29	0.9300
C9—C14	1.404 (8)	C30—C31	1.382 (8)
C10—C11	1.368 (8)	C30—H30	0.9300
C10—H10	0.9300	C31—C32	1.356 (9)
C11—C12	1.379 (8)	C31—H31	0.9300
C11—H11	0.9300	C32—H32	0.9300
C12—C13	1.365 (8)	C33—C34	1.541 (8)
C12—H12	0.9300	C33—H33A	0.9700
C13—C14	1.351 (8)	C33—H33B	0.9700
C13—H13	0.9300	C34—H34A	0.9700
C14—H14	0.9300	C34—H34B	0.9700
S1—Ni1—S2	91.96 (5)	C20—C15—P1	122.5 (4)
S1—Ni1—P2	89.41 (6)	C16—C15—P1	119.7 (4)
S2—Ni1—P2	175.21 (6)	C17—C16—C15	121.3 (5)
S1—Ni1—P1	170.01 (6)	C17—C16—H16	119.3
S2—Ni1—P1	93.06 (6)	C15—C16—H16	119.3
P2—Ni1—P1	86.29 (6)	C18—C17—C16	120.7 (5)
C9—P1—C15	107.9 (3)	C18—C17—H17	119.7
C9—P1—C33	103.4 (3)	C16—C17—H17	119.7
C15—P1—C33	103.6 (3)	C17—C18—C19	118.7 (5)
C9—P1—Ni1	122.87 (19)	C17—C18—H18	120.7
C15—P1—Ni1	108.4 (2)	C19—C18—H18	120.7
C33—P1—Ni1	109.03 (19)	C20—C19—C18	120.3 (5)
C27—P2—C34	103.6 (3)	C20—C19—H19	119.9
C27—P2—C21	106.8 (3)	C18—C19—H19	119.9
C34—P2—C21	106.5 (3)	C15—C20—C19	121.0 (5)
C27—P2—Ni1	116.9 (2)	C15—C20—H20	119.5
C34—P2—Ni1	110.08 (19)	C19—C20—H20	119.5
C21—P2—Ni1	112.14 (18)	C22—C21—C26	121.7 (5)
C1—S1—Ni1	104.9 (2)	C22—C21—P2	121.1 (4)
C8—S2—Ni1	104.85 (18)	C26—C21—P2	116.2 (4)
C1—N1—C2	116.7 (5)	C21—C22—C23	121.5 (5)
C8—N2—C7	118.4 (5)	C21—C22—H22	119.2
N1—C1—C8	122.0 (5)	C23—C22—H22	119.2
N1—C1—S1	118.9 (4)	C24—C23—C22	117.1 (5)
C8—C1—S1	119.1 (4)	C24—C23—H23	121.5
N1—C2—C7	121.9 (5)	C22—C23—H23	121.5
N1—C2—C3	119.5 (6)	C23—C24—C25	123.7 (5)
C7—C2—C3	118.7 (5)	C23—C24—H24	118.1
C4—C3—C2	119.5 (6)	C25—C24—H24	118.1
C4—C3—H3	120.3	C24—C25—C26	118.3 (5)
C2—C3—H3	120.3	C24—C25—H25	120.8
C3—C4—C5	121.8 (6)	C26—C25—H25	120.8
C3—C4—H4	119.1	C21—C26—C25	115.4 (5)
C5—C4—H4	119.1	C21—C26—H26	122.3
C4—C5—C6	121.1 (5)	C25—C26—H26	122.3
C4—C5—H5	119.5	C28—C27—C32	119.2 (5)
C6—C5—H5	119.5	C28—C27—P2	122.5 (4)
C5—C6—C7	120.0 (6)	C32—C27—P2	118.2 (4)
C5—C6—H6	120.0	C27—C28—C29	120.8 (6)
C7—C6—H6	120.0	C27—C28—H28	119.6
N2—C7—C2	120.6 (5)	C29—C28—H28	119.6
N2—C7—C6	120.4 (6)	C28—C29—C30	119.9 (6)
C2—C7—C6	118.9 (6)	C28—C29—H29	120.1
N2—C8—C1	120.4 (5)	C30—C29—H29	120.1
N2—C8—S2	120.6 (4)	C31—C30—C29	119.0 (6)
C1—C8—S2	118.9 (4)	C31—C30—H30	120.5
C10—C9—C14	117.8 (5)	C29—C30—H30	120.5
C10—C9—P1	121.8 (4)	C32—C31—C30	120.1 (5)
C14—C9—P1	120.3 (4)	C32—C31—H31	119.9
C9—C10—C11	121.0 (5)	C30—C31—H31	119.9
C9—C10—H10	119.5	C31—C32—C27	121.0 (6)
C11—C10—H10	119.5	C31—C32—H32	119.5
C10—C11—C12	120.4 (5)	C27—C32—H32	119.5
C10—C11—H11	119.8	C34—C33—P1	107.8 (4)
C12—C11—H11	119.8	C34—C33—H33A	110.1
C13—C12—C11	119.2 (5)	P1—C33—H33A	110.1
C13—C12—H12	120.4	C34—C33—H33B	110.1
C11—C12—H12	120.4	P1—C33—H33B	110.1
C14—C13—C12	120.6 (5)	H33A—C33—H33B	108.5
C14—C13—H13	119.7	C33—C34—P2	107.2 (4)
C12—C13—H13	119.7	C33—C34—H34A	110.3
C13—C14—C9	121.0 (6)	P2—C34—H34A	110.3
C13—C14—H14	119.5	C33—C34—H34B	110.3
C9—C14—H14	119.5	P2—C34—H34B	110.3
C20—C15—C16	117.7 (5)	H34A—C34—H34B	108.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···S2^i	0.93	2.89	3.748 (3)	153

Symmetry code: (i) −x, y−1/2, −z+1/2.