{N-Anilino-2-[(2-oxidophen­yl)methylenehydrazono]-2-sulfidoacetamide}pyridinenickel(II)

The title compound is a square-planar tetra­coordinate Ni complex, [Ni(C₁₅H₁₁N₃O₂S)(C₅H₅N)]. The coordination of the Ni atom can also be considered to be highly elongated square bipyramidal, this being accomplished by an S and an O atom of adjacent mol­ecules. In this way, polymeric chains are formed extending in the b direction

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.044
• wR factor = 0.084
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      55.00 A   3  

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 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
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2002, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).

[Pyridine (2–aniline–N–[–(2–oxyphenyl)methylene]–2–oxoethanehydrazonethionic acid)Ni(II)]

Crystal data

[Ni(C15H11N3O2S)(C5H5N)]	F(000) = 1792
Mr = 435.14	Dx = 1.513 Mg m^−3
Monoclinic, C2/c	Melting point = 470–473. K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 41.91 (2) Å	Cell parameters from 25 reflections
b = 3.952 (3) Å	θ = 13–16°
c = 28.840 (13) Å	µ = 1.15 mm^−1
β = 126.87 (4)°	T = 298 K
V = 3821 (4) Å^3	Needle, dark red
Z = 8	0.3 × 0.3 × 0.3 mm

Data collection

Enraf–Nonius CAD-4 diffractometer	2393 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tube	Rint = 0.081
Graphite monochromator	θmax = 27.0°, θmin = 1.2°
Non–profiled ω/2θ scans	h = −52→42
Absorption correction: psi-scan North et al., 1968'	k = 0→5
Tmin = 0.684, Tmax = 0.708	l = 0→36
4228 measured reflections	1 standard reflections every 200 reflections
4134 independent reflections	intensity decay: 1%

Refinement

Refinement on F^2	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	w = 1/[σ^2(Fo^2) + (0.0236P)^2] where P = (Fo^2 + 2Fc^2)/3
4134 reflections	(Δ/σ)max = 0.011
257 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

Experimental. Number of psi-scan sets used was 3, Theta correction was applied. Averaged transmission function was used. No Fourier smoothing was applied.

The ¹H NMR spectra were measured on a Bruker WM–200 (200 MHz) instrument in DMSO–d₆. The ¹³C NMR spectra were recorded on a Bruker WM–200 instrument (50 MHz) in DMSO–d₆. The melting points were measured on a Boetius hot–stage apparatus and are uncorrected. The reaction mixtures were analyzed and the purities of the reaction products were checked by TLC using a 1:1 ethyl acetate/hexane solvent system and ethyl acetate. No data for complex (3) are available in the CCDC (Allen, 2002, last update 04.2004).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.114848 (12)	0.25864 (15)	0.324324 (17)	0.03365 (13)
S	0.08158 (2)	−0.0176 (3)	0.34654 (4)	0.0392 (2)
O1	0.14214 (6)	0.4877 (7)	0.30171 (9)	0.0380 (6)
C1	0.17906 (9)	0.5975 (9)	0.33509 (14)	0.0329 (8)
C2	0.19446 (9)	0.7672 (11)	0.30921 (14)	0.0440 (9)
H2	0.1781	0.8001	0.2693	0.053*
C3	0.23297 (10)	0.8840 (10)	0.34177 (16)	0.0456 (10)
H3	0.2423	0.9970	0.3237	0.055*
C4	0.25837 (10)	0.8353 (10)	0.40171 (15)	0.0441 (11)
H4	0.2845	0.9130	0.4236	0.053*
C5	0.24427 (9)	0.6724 (9)	0.42760 (14)	0.0371 (10)
H5	0.2612	0.6385	0.4675	0.045*
C6	0.20473 (9)	0.5538 (9)	0.39552 (13)	0.0316 (8)
C7	0.19199 (9)	0.3962 (9)	0.42607 (13)	0.0346 (9)
H7	0.2105	0.3793	0.4661	0.042*
N8	0.15655 (7)	0.2732 (8)	0.40278 (10)	0.0330 (7)
N9	0.15210 (8)	0.1465 (8)	0.44405 (11)	0.0373 (8)
C10	0.11717 (9)	0.0105 (10)	0.41945 (14)	0.0346 (8)
C11	0.10774 (10)	−0.1305 (9)	0.45909 (15)	0.0380 (9)
O11	0.07697 (7)	−0.2818 (9)	0.43976 (10)	0.0609 (8)
N12	0.13658 (9)	−0.0708 (9)	0.51600 (13)	0.0437 (9)
H12	0.1570 (9)	0.012 (10)	0.5238 (13)	0.044 (12)*
C13	0.13700 (11)	−0.1508 (9)	0.56412 (15)	0.0404 (10)
C14	0.17041 (11)	−0.0620 (11)	0.61850 (15)	0.0516 (11)
H14	0.1915	0.0476	0.6222	0.062*
C15	0.17294 (14)	−0.1335 (12)	0.66731 (17)	0.0685 (15)
H15	0.1958	−0.0758	0.7037	0.082*
C16	0.14203 (15)	−0.2887 (13)	0.6623 (2)	0.0710 (14)
H16	0.1435	−0.3317	0.6953	0.085*
C17	0.10873 (15)	−0.3817 (12)	0.6089 (2)	0.0699 (14)
H17	0.0878	−0.4891	0.6059	0.084*
C18	0.10595 (12)	−0.3167 (11)	0.55903 (17)	0.0559 (12)
H18	0.0835	−0.3838	0.5229	0.067*
N21	0.07048 (7)	0.2359 (9)	0.24414 (10)	0.0354 (7)
C22	0.07490 (11)	0.0953 (10)	0.20624 (15)	0.0453 (10)
H22	0.0996	0.0046	0.2198	0.054*
C23	0.04424 (11)	0.0793 (11)	0.14755 (15)	0.0521 (11)
H23	0.0481	−0.0217	0.1222	0.063*
C24	0.00781 (11)	0.2159 (12)	0.12743 (15)	0.0561 (12)
H24	−0.0133	0.2079	0.0882	0.067*
C25	0.00307 (10)	0.3637 (10)	0.16591 (15)	0.0519 (12)
H25	−0.0213	0.4571	0.1532	0.062*
C26	0.03487 (9)	0.3713 (10)	0.22336 (14)	0.0430 (11)
H26	0.0316	0.4752	0.2492	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0323 (2)	0.0345 (3)	0.0329 (2)	0.0011 (3)	0.01881 (16)	0.0010 (3)
S	0.0388 (5)	0.0399 (6)	0.0376 (5)	−0.0054 (5)	0.0222 (4)	−0.0034 (5)
O1	0.0343 (12)	0.0430 (17)	0.0344 (12)	0.0003 (13)	0.0195 (10)	0.0036 (13)
C1	0.0356 (18)	0.026 (2)	0.0401 (18)	0.0033 (16)	0.0244 (15)	0.0001 (17)
C2	0.0426 (18)	0.050 (3)	0.0424 (18)	0.002 (2)	0.0271 (16)	0.004 (2)
C3	0.050 (2)	0.038 (3)	0.063 (2)	−0.0026 (19)	0.042 (2)	0.003 (2)
C4	0.0359 (18)	0.038 (3)	0.057 (2)	−0.0045 (18)	0.0273 (18)	−0.003 (2)
C5	0.0338 (17)	0.033 (3)	0.0420 (18)	0.0008 (17)	0.0216 (15)	−0.0024 (17)
C6	0.0376 (17)	0.022 (2)	0.0380 (18)	0.0035 (17)	0.0239 (15)	0.0003 (17)
C7	0.0350 (17)	0.032 (2)	0.0320 (17)	0.0030 (17)	0.0174 (15)	−0.0002 (17)
N8	0.0378 (14)	0.0269 (18)	0.0383 (14)	0.0022 (17)	0.0248 (12)	−0.0021 (17)
N9	0.0422 (15)	0.038 (2)	0.0354 (14)	−0.0022 (15)	0.0253 (13)	−0.0009 (14)
C10	0.0384 (18)	0.027 (2)	0.0404 (18)	0.0027 (18)	0.0250 (16)	0.0008 (18)
C11	0.044 (2)	0.034 (2)	0.0418 (19)	0.0025 (18)	0.0290 (17)	0.0029 (18)
O11	0.0515 (15)	0.083 (2)	0.0482 (14)	−0.0237 (19)	0.0298 (13)	−0.0060 (18)
N12	0.0415 (18)	0.051 (2)	0.0398 (17)	−0.0099 (18)	0.0250 (15)	−0.0032 (17)
C13	0.057 (2)	0.034 (3)	0.044 (2)	0.0050 (19)	0.0372 (19)	0.0038 (18)
C14	0.061 (2)	0.054 (3)	0.049 (2)	0.004 (2)	0.038 (2)	0.003 (2)
C15	0.094 (3)	0.071 (4)	0.045 (2)	0.018 (3)	0.044 (2)	0.004 (2)
C16	0.119 (4)	0.056 (4)	0.077 (3)	0.024 (4)	0.079 (3)	0.018 (3)
C17	0.113 (4)	0.052 (3)	0.087 (3)	0.002 (3)	0.083 (3)	0.007 (3)
C18	0.076 (3)	0.047 (3)	0.066 (2)	−0.004 (2)	0.054 (2)	0.000 (2)
N21	0.0380 (14)	0.0341 (18)	0.0363 (14)	0.0007 (18)	0.0235 (12)	0.0047 (18)
C22	0.050 (2)	0.045 (3)	0.045 (2)	−0.003 (2)	0.0311 (18)	−0.002 (2)
C23	0.066 (3)	0.054 (3)	0.041 (2)	−0.004 (2)	0.035 (2)	−0.005 (2)
C24	0.051 (2)	0.061 (3)	0.0378 (19)	−0.011 (3)	0.0164 (17)	0.004 (3)
C25	0.0369 (19)	0.056 (3)	0.051 (2)	−0.002 (2)	0.0201 (18)	0.009 (2)
C26	0.0369 (18)	0.046 (3)	0.045 (2)	0.0035 (18)	0.0238 (17)	0.0054 (19)

Geometric parameters (Å, º)

Ni—N8	1.853 (3)	N12—C13	1.413 (4)
Ni—O1	1.857 (2)	N12—H12	0.81 (3)
Ni—N21	1.911 (3)	C13—C14	1.381 (5)
Ni—S	2.1490 (13)	C13—C18	1.384 (5)
S—C10	1.701 (3)	C14—C15	1.376 (5)
O1—C1	1.312 (4)	C14—H14	0.9300
C1—C6	1.405 (4)	C15—C16	1.360 (6)
C1—C2	1.415 (4)	C15—H15	0.9300
C2—C3	1.371 (4)	C16—C17	1.370 (6)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.397 (5)	C17—C18	1.396 (5)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.361 (4)	C18—H18	0.9300
C4—H4	0.9300	N21—C22	1.334 (4)
C5—C6	1.408 (4)	N21—C26	1.341 (4)
C5—H5	0.9300	C22—C23	1.382 (5)
C6—C7	1.419 (4)	C22—H22	0.9300
C7—N8	1.303 (4)	C23—C24	1.377 (5)
C7—H7	0.9300	C23—H23	0.9300
N8—N9	1.403 (3)	C24—C25	1.370 (5)
N9—C10	1.299 (4)	C24—H24	0.9300
C10—C11	1.522 (4)	C25—C26	1.368 (4)
C11—O11	1.212 (4)	C25—H25	0.9300
C11—N12	1.353 (4)	C26—H26	0.9300
N8—Ni—O1	94.90 (12)	C11—N12—C13	128.9 (3)
N8—Ni—N21	177.66 (12)	C11—N12—H12	116 (2)
O1—Ni—N21	87.42 (11)	C13—N12—H12	115 (2)
N8—Ni—S	87.53 (10)	C14—C13—C18	119.3 (3)
O1—Ni—S	177.30 (8)	C14—C13—N12	117.7 (3)
N21—Ni—S	90.15 (10)	C18—C13—N12	123.0 (3)
C10—S—Ni	95.21 (13)	C15—C14—C13	120.8 (4)
C1—O1—Ni	127.4 (2)	C15—C14—H14	119.6
O1—C1—C6	123.9 (3)	C13—C14—H14	119.6
O1—C1—C2	118.7 (3)	C16—C15—C14	120.0 (4)
C6—C1—C2	117.4 (3)	C16—C15—H15	120.0
C3—C2—C1	121.4 (3)	C14—C15—H15	120.0
C3—C2—H2	119.3	C15—C16—C17	120.2 (4)
C1—C2—H2	119.3	C15—C16—H16	119.9
C2—C3—C4	120.7 (3)	C17—C16—H16	119.9
C2—C3—H3	119.6	C16—C17—C18	120.6 (4)
C4—C3—H3	119.6	C16—C17—H17	119.7
C5—C4—C3	119.0 (3)	C18—C17—H17	119.7
C5—C4—H4	120.5	C13—C18—C17	119.1 (4)
C3—C4—H4	120.5	C13—C18—H18	120.5
C4—C5—C6	121.6 (3)	C17—C18—H18	120.5
C4—C5—H5	119.2	C22—N21—C26	117.7 (3)
C6—C5—H5	119.2	C22—N21—Ni	119.9 (2)
C1—C6—C5	119.9 (3)	C26—N21—Ni	122.4 (2)
C1—C6—C7	122.0 (3)	N21—C22—C23	122.6 (4)
C5—C6—C7	118.1 (3)	N21—C22—H22	118.7
N8—C7—C6	125.5 (3)	C23—C22—H22	118.7
N8—C7—H7	117.2	C24—C23—C22	118.6 (4)
C6—C7—H7	117.2	C24—C23—H23	120.7
C7—N8—N9	112.7 (3)	C22—C23—H23	120.7
C7—N8—Ni	126.1 (2)	C25—C24—C23	119.3 (3)
N9—N8—Ni	121.1 (2)	C25—C24—H24	120.4
C10—N9—N8	111.3 (3)	C23—C24—H24	120.4
N9—C10—C11	117.1 (3)	C26—C25—C24	118.8 (4)
N9—C10—S	124.5 (3)	C26—C25—H25	120.6
C11—C10—S	118.3 (3)	C24—C25—H25	120.6
O11—C11—N12	125.0 (3)	N21—C26—C25	123.1 (4)
O11—C11—C10	121.3 (3)	N21—C26—H26	118.4
N12—C11—C10	113.7 (3)	C25—C26—H26	118.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N12—H12···N9	0.81 (3)	2.25 (3)	2.662 (4)	112 (3)