Crystal structure and Hirshfeld surface analysis of bis­{(Z)-N′-[(E)-(furan-2-yl)methyl­idene]carbamo­hydrazono­thio­ato}nickel(II) methanol disolvate

In the title complex, the Ni^II atom is coordinated by the S and N atoms of two N′-[(Z)-(furan-2-yl)methyl­idene]carbamohydrazono­thioic acid ligands in a distorted square-planar geometry.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.032
• wR factor = 0.088
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note

Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          3 Report
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ni1      --N1       .        5.3 s.u.
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O1       .      106.2 Degree
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1       (II)      .       2.31 Info
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Theta(Min).          3 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          3 Note
PLAT933_ALERT_2_G Number of HKL-OMIT Records in Embedded .res File          2 Note
PLAT941_ALERT_3_G Average HKL Measurement Multiplicity ...........        4.0 Low
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          0 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   9 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: APEX4 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

Bis{(Z)-N'-[(E)-(furan-2-yl)methylidene]carbamohydrazonothioato}nickel(II) methanol disolvate

Crystal data

[Ni(C6H6N3OS)2]·2CH4O	Z = 1
Mr = 459.19	F(000) = 238
Triclinic, P1	Dx = 1.464 Mg m^−3
a = 6.5394 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9611 (15) Å	Cell parameters from 2724 reflections
c = 10.2020 (15) Å	θ = 2.7–26.4°
α = 67.965 (5)°	µ = 1.16 mm^−1
β = 79.666 (6)°	T = 296 K
γ = 70.349 (6)°	Prism, orange
V = 520.92 (15) Å^3	0.26 × 0.21 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	1633 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.046
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θmax = 26.4°, θmin = 3.3°
Tmin = 0.735, Tmax = 0.861	h = −8→8
8497 measured reflections	k = −11→11
2134 independent reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0459P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max < 0.001
2134 reflections	Δρmax = 0.25 e Å^−3
125 parameters	Δρmin = −0.21 e Å^−3
0 restraints

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	Uiso*/Ueq
Ni1	0.500000	0.000000	0.500000	0.03949 (16)
S1	0.21552 (9)	0.08780 (8)	0.37725 (6)	0.0544 (2)
O1	0.8206 (3)	0.4874 (2)	0.41926 (18)	0.0592 (5)
O2	0.7620 (3)	0.3261 (2)	0.05737 (16)	0.0534 (4)
H2O	0.634939	0.350050	0.108389	0.080*
N1	0.5375 (3)	0.2167 (2)	0.39689 (17)	0.0403 (4)
N2	0.4320 (3)	0.3178 (2)	0.27263 (18)	0.0428 (4)
N3	0.1595 (3)	0.3562 (2)	0.1429 (2)	0.0558 (6)
H3A	0.195718	0.448305	0.083360	0.067*
H3B	0.032648	0.349515	0.126510	0.067*
C1	0.6747 (4)	0.4539 (3)	0.3592 (2)	0.0446 (5)
C2	0.8207 (5)	0.6480 (3)	0.3424 (3)	0.0688 (8)
H2	0.905332	0.703098	0.359617	0.083*
C3	0.6847 (5)	0.7162 (3)	0.2396 (3)	0.0679 (8)
H3	0.658018	0.824589	0.173586	0.082*
C4	0.5872 (4)	0.5926 (3)	0.2494 (3)	0.0544 (6)
H4	0.483563	0.604491	0.191646	0.065*
C5	0.6538 (3)	0.2881 (3)	0.4311 (2)	0.0440 (5)
H5	0.732223	0.223902	0.511529	0.053*
C6	0.2750 (3)	0.2665 (3)	0.2568 (2)	0.0415 (5)
C7	0.8122 (6)	0.1616 (4)	0.0563 (3)	0.0883 (10)
H7A	0.683980	0.143664	0.039468	0.132*
H7B	0.864640	0.082516	0.146089	0.132*
H7C	0.922412	0.146101	−0.017494	0.132*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0337 (2)	0.0371 (3)	0.0388 (2)	−0.01571 (17)	−0.00740 (15)	0.00392 (17)
S1	0.0428 (3)	0.0477 (4)	0.0586 (4)	−0.0248 (3)	−0.0200 (3)	0.0150 (3)
O1	0.0688 (12)	0.0533 (11)	0.0615 (11)	−0.0308 (9)	−0.0191 (8)	−0.0081 (8)
O2	0.0559 (10)	0.0439 (10)	0.0575 (10)	−0.0225 (8)	0.0064 (8)	−0.0116 (7)
N1	0.0346 (9)	0.0423 (10)	0.0352 (9)	−0.0157 (8)	−0.0070 (7)	0.0024 (8)
N2	0.0419 (10)	0.0435 (11)	0.0368 (10)	−0.0213 (8)	−0.0095 (8)	0.0040 (8)
N3	0.0505 (12)	0.0567 (13)	0.0511 (11)	−0.0293 (10)	−0.0223 (9)	0.0121 (10)
C1	0.0482 (13)	0.0444 (13)	0.0435 (12)	−0.0202 (10)	−0.0031 (10)	−0.0114 (11)
C2	0.087 (2)	0.0537 (17)	0.078 (2)	−0.0385 (15)	−0.0121 (16)	−0.0171 (15)
C3	0.095 (2)	0.0426 (15)	0.0671 (18)	−0.0308 (15)	−0.0135 (16)	−0.0068 (13)
C4	0.0675 (16)	0.0402 (14)	0.0540 (15)	−0.0191 (12)	−0.0152 (12)	−0.0063 (12)
C5	0.0457 (12)	0.0435 (13)	0.0366 (12)	−0.0171 (10)	−0.0090 (9)	−0.0005 (10)
C6	0.0350 (11)	0.0408 (12)	0.0391 (12)	−0.0152 (9)	−0.0050 (9)	0.0017 (10)
C7	0.101 (3)	0.0552 (19)	0.111 (3)	−0.0192 (17)	−0.003 (2)	−0.0358 (19)

Geometric parameters (Å, º)

Ni1—N1	1.9055 (17)	N3—H3A	0.8997
Ni1—N1^i	1.9055 (17)	N3—H3B	0.9000
Ni1—S1	2.1818 (6)	C1—C4	1.354 (3)
Ni1—S1^i	2.1818 (6)	C1—C5	1.431 (3)
S1—C6	1.731 (2)	C2—C3	1.323 (4)
O1—C2	1.357 (3)	C2—H2	0.9300
O1—C1	1.384 (3)	C3—C4	1.419 (3)
O2—C7	1.402 (3)	C3—H3	0.9300
O2—H2O	0.9032	C4—H4	0.9300
N1—C5	1.305 (3)	C5—H5	0.9300
N1—N2	1.391 (2)	C7—H7A	0.9600
N2—C6	1.313 (3)	C7—H7B	0.9600
N3—C6	1.332 (3)	C7—H7C	0.9600
N1—Ni1—N1^i	180.0	C3—C2—H2	124.4
N1—Ni1—S1	85.69 (5)	O1—C2—H2	124.4
N1^i—Ni1—S1	94.31 (5)	C2—C3—C4	107.0 (2)
N1—Ni1—S1^i	94.31 (5)	C2—C3—H3	126.5
N1^i—Ni1—S1^i	85.69 (5)	C4—C3—H3	126.5
S1—Ni1—S1^i	180.0	C1—C4—C3	106.5 (2)
C6—S1—Ni1	95.83 (7)	C1—C4—H4	126.7
C2—O1—C1	106.13 (18)	C3—C4—H4	126.7
C7—O2—H2O	109.2	N1—C5—C1	127.45 (19)
C5—N1—N2	112.86 (16)	N1—C5—H5	116.3
C5—N1—Ni1	126.69 (14)	C1—C5—H5	116.3
N2—N1—Ni1	120.44 (13)	N2—C6—N3	117.99 (17)
C6—N2—N1	112.74 (15)	N2—C6—S1	122.47 (15)
C6—N3—H3A	116.5	N3—C6—S1	119.54 (16)
C6—N3—H3B	127.8	O2—C7—H7A	109.5
H3A—N3—H3B	114.4	O2—C7—H7B	109.5
C4—C1—O1	109.12 (19)	H7A—C7—H7B	109.5
C4—C1—C5	138.1 (2)	O2—C7—H7C	109.5
O1—C1—C5	112.71 (19)	H7A—C7—H7C	109.5
C3—C2—O1	111.2 (2)	H7B—C7—H7C	109.5
C5—N1—N2—C6	−163.93 (19)	N2—N1—C5—C1	2.4 (3)
Ni1—N1—N2—C6	15.0 (2)	Ni1—N1—C5—C1	−176.40 (17)
C2—O1—C1—C4	−0.7 (3)	C4—C1—C5—N1	5.6 (5)
C2—O1—C1—C5	−179.0 (2)	O1—C1—C5—N1	−176.8 (2)
C1—O1—C2—C3	0.3 (3)	N1—N2—C6—N3	178.56 (19)
O1—C2—C3—C4	0.2 (3)	N1—N2—C6—S1	−1.8 (3)
O1—C1—C4—C3	0.8 (3)	Ni1—S1—C6—N2	−8.9 (2)
C5—C1—C4—C3	178.5 (3)	Ni1—S1—C6—N3	170.73 (18)
C2—C3—C4—C1	−0.6 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···N2	0.90	1.94	2.788 (3)	156
N3—H3A···O2^ii	0.90	2.07	2.964 (3)	173
N3—H3B···O2^iii	0.90	2.12	3.009 (3)	171
C4—H4···N2	0.93	2.51	2.882 (3)	104
C5—H5···S1^i	0.93	2.51	3.102 (3)	121

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z; (iii) x−1, y, z.