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The title compound, [Ni(C18H18N6O2S2)](ClO4)2·2CH4O, (I), has been prepared by the reaction of 2,2'-(ethyl­ene­dioxy)­dibenz­aldehyde bis­(thio­semicarbazone), L, with nickel(II) perchlorate. The chemical structural unit, which is twice the asymmetric unit of (I), consists of one NiII ion, one ligand L, two methanol solvent mol­ecules and two uncoordinated perchlorate anions. The Ni atom lies on a crystallographic twofold axis of rotation. The ligand L coordinates to the central Ni atom through two O atoms, two S atoms and two N atoms, giving a distorted octahedral environment. The S and O atoms occupy equatorial positions, and are nearly coplanar with the nickel, while the two N atoms occupy axial positions, with the N-Ni-N angle being 177.06 (18)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804017192/hg6062sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804017192/hg6062Isup2.hkl
Contains datablock I

CCDC reference: 248744

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.158
  • Data-to-parameter ratio = 15.7

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.651 0.866 Tmin' and Tmax expected: 0.810 0.866 RR' = 0.804 Please check that your absorption correction is appropriate. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.80 PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 6018.00 Ang-3 PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors for Cl1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N1 -NI1 -N1 -C8 65.60 0.40 6.554 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 21 N1 -NI1 -N1 -N2 -119.80 0.30 6.554 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

[2,2'-(ethylenedioxy)dibenzaldehyde bis(thiosemicarbazone)]nickel(II) diperchlorate methanol disolvate top
Crystal data top
[Ni(C18H18N6O2S2)](ClO4)2·2CH4ODx = 1.625 Mg m3
Mr = 736.20Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 934 reflections
Hall symbol: -I 4adθ = 2.5–25.5°
a = 13.586 (8) ŵ = 1.03 mm1
c = 32.60 (4) ÅT = 293 K
V = 6018 (9) Å3Block, green
Z = 80.20 × 0.18 × 0.14 mm
F(000) = 3024
Data collection top
Bruker SMART CCD area-detector
diffractometer
3097 independent reflections
Radiation source: fine-focus sealed tube2286 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
φ and ω scansθmax = 26.5°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1016
Tmin = 0.651, Tmax = 0.866k = 1617
17255 measured reflectionsl = 4035
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0804P)2 + 15.2797P]
where P = (Fo2 + 2Fc2)/3
3097 reflections(Δ/σ)max < 0.002
197 parametersΔρmax = 0.70 e Å3
0 restraintsΔρmin = 0.81 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.

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 (Å2) top
xyzUiso*/Ueq
Ni10.50000.25000.61515 (2)0.0280 (2)
S10.42768 (7)0.13687 (9)0.56983 (4)0.0416 (3)
O10.5256 (2)0.3430 (2)0.66764 (9)0.0349 (6)
N10.3632 (2)0.3108 (2)0.61675 (10)0.0299 (7)
N20.2887 (2)0.2576 (3)0.59843 (11)0.0355 (8)
N30.2353 (3)0.1289 (3)0.56052 (12)0.0476 (10)
H3A0.17630.15000.56420.057*
H3B0.24540.07650.54630.057*
C10.5388 (3)0.2899 (3)0.70612 (13)0.0402 (10)
H1A0.52980.33360.72930.048*
H1B0.60410.26140.70760.048*
C20.4913 (3)0.4393 (3)0.67024 (14)0.0388 (10)
C30.5450 (4)0.5081 (4)0.69168 (17)0.0524 (13)
H30.60300.49020.70480.063*
C40.5116 (5)0.6038 (4)0.6934 (2)0.0682 (17)
H40.54690.65030.70830.082*
C50.4275 (5)0.6312 (4)0.6736 (2)0.0737 (18)
H50.40710.69650.67430.088*
C60.3732 (4)0.5631 (3)0.65267 (18)0.0550 (13)
H60.31530.58230.63970.066*
C70.4038 (3)0.4648 (3)0.65059 (14)0.0392 (10)
C80.3386 (3)0.3965 (3)0.63031 (14)0.0375 (10)
H80.27360.41590.62670.045*
C90.3103 (3)0.1767 (3)0.57670 (12)0.0330 (9)
Cl10.84538 (9)0.32414 (8)0.68629 (4)0.0461 (3)
O20.9019 (5)0.3441 (4)0.6506 (2)0.122 (2)
O30.7598 (4)0.3809 (4)0.6790 (2)0.1092 (19)
O40.8219 (4)0.2239 (3)0.68696 (16)0.0860 (15)
O50.8919 (5)0.3602 (4)0.7211 (2)0.138 (3)
O60.7701 (4)0.5213 (3)0.75400 (15)0.0861 (15)
H6A0.79960.47360.74480.129*
C100.7975 (6)0.6057 (5)0.7324 (2)0.091 (2)
H10A0.78800.66260.74940.137*
H10B0.75790.61160.70820.137*
H10C0.86560.60100.72480.137*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0202 (4)0.0315 (4)0.0323 (4)0.0005 (3)0.0000.000
S10.0264 (5)0.0499 (7)0.0485 (7)0.0009 (4)0.0012 (5)0.0175 (5)
O10.0392 (16)0.0299 (14)0.0355 (15)0.0005 (12)0.0053 (12)0.0000 (12)
N10.0231 (16)0.0336 (18)0.0329 (18)0.0024 (13)0.0007 (13)0.0010 (14)
N20.0226 (16)0.044 (2)0.040 (2)0.0005 (14)0.0032 (14)0.0031 (16)
N30.0282 (19)0.057 (2)0.057 (2)0.0068 (17)0.0055 (17)0.017 (2)
C10.047 (3)0.040 (2)0.034 (2)0.004 (2)0.0085 (19)0.0015 (18)
C20.039 (2)0.032 (2)0.046 (3)0.0054 (18)0.0053 (19)0.0001 (18)
C30.053 (3)0.040 (3)0.064 (3)0.014 (2)0.006 (2)0.005 (2)
C40.071 (4)0.039 (3)0.095 (5)0.019 (3)0.006 (3)0.015 (3)
C50.082 (4)0.028 (3)0.112 (5)0.001 (3)0.002 (4)0.012 (3)
C60.056 (3)0.037 (3)0.072 (4)0.007 (2)0.002 (3)0.001 (2)
C70.039 (2)0.031 (2)0.047 (3)0.0001 (18)0.005 (2)0.0014 (19)
C80.028 (2)0.041 (2)0.044 (2)0.0086 (18)0.0000 (18)0.0015 (19)
C90.027 (2)0.040 (2)0.032 (2)0.0018 (17)0.0033 (16)0.0001 (17)
Cl10.0498 (7)0.0334 (6)0.0551 (7)0.0033 (5)0.0020 (5)0.0015 (5)
O20.165 (6)0.065 (3)0.137 (5)0.035 (3)0.086 (4)0.012 (3)
O30.088 (4)0.075 (3)0.165 (5)0.022 (3)0.040 (4)0.022 (3)
O40.100 (3)0.036 (2)0.121 (4)0.010 (2)0.013 (3)0.013 (2)
O50.195 (7)0.099 (4)0.119 (5)0.015 (4)0.094 (5)0.016 (4)
O60.109 (4)0.067 (3)0.082 (3)0.004 (3)0.049 (3)0.019 (2)
C100.109 (6)0.086 (5)0.079 (5)0.014 (4)0.032 (4)0.001 (4)
Geometric parameters (Å, º) top
Ni1—N1i2.034 (3)C3—C41.378 (8)
Ni1—N12.034 (3)C3—H30.9300
Ni1—O12.156 (3)C4—C51.366 (9)
Ni1—O1i2.156 (3)C4—H40.9300
Ni1—S1i2.3475 (18)C5—C61.365 (8)
Ni1—S12.3476 (18)C5—H50.9300
S1—C91.699 (4)C6—C71.401 (6)
O1—C21.391 (5)C6—H60.9300
O1—C11.459 (5)C7—C81.442 (6)
N1—C81.290 (5)C8—H80.9300
N1—N21.380 (5)Cl1—O51.389 (5)
N2—C91.341 (5)Cl1—O41.399 (4)
N3—C91.318 (5)Cl1—O31.415 (5)
N3—H3A0.8600Cl1—O21.419 (5)
N3—H3B0.8600O6—C101.396 (8)
C1—C1i1.511 (9)O6—H6A0.8200
C1—H1A0.9700C10—H10A0.9600
C1—H1B0.9700C10—H10B0.9600
C2—C31.376 (6)C10—H10C0.9600
C2—C71.395 (6)
N1i—Ni1—N1177.06 (18)C2—C3—C4119.2 (5)
N1i—Ni1—O194.02 (12)C2—C3—H3120.4
N1—Ni1—O183.64 (12)C4—C3—H3120.4
N1i—Ni1—O1i83.64 (12)C5—C4—C3120.9 (5)
N1—Ni1—O1i94.02 (12)C5—C4—H4119.6
O1—Ni1—O1i74.90 (16)C3—C4—H4119.6
N1i—Ni1—S1i84.24 (10)C6—C5—C4120.3 (5)
N1—Ni1—S1i97.62 (10)C6—C5—H5119.9
O1—Ni1—S1i92.77 (11)C4—C5—H5119.9
O1i—Ni1—S1i162.01 (8)C5—C6—C7120.7 (5)
N1i—Ni1—S197.62 (10)C5—C6—H6119.7
N1—Ni1—S184.24 (10)C7—C6—H6119.7
O1—Ni1—S1162.01 (8)C2—C7—C6117.9 (4)
O1i—Ni1—S192.77 (11)C2—C7—C8125.0 (4)
S1i—Ni1—S1101.98 (10)C6—C7—C8117.0 (4)
C9—S1—Ni195.83 (14)N1—C8—C7125.4 (4)
C2—O1—C1117.0 (3)N1—C8—H8117.3
C2—O1—Ni1123.1 (3)C7—C8—H8117.3
C1—O1—Ni1114.4 (2)N3—C9—N2116.6 (4)
C8—N1—N2115.5 (3)N3—C9—S1121.1 (3)
C8—N1—Ni1127.7 (3)N2—C9—S1122.4 (3)
N2—N1—Ni1116.5 (2)O5—Cl1—O4115.7 (4)
C9—N2—N1119.9 (3)O5—Cl1—O3108.6 (4)
C9—N3—H3A120.0O4—Cl1—O3110.2 (3)
C9—N3—H3B120.0O5—Cl1—O2110.9 (5)
H3A—N3—H3B120.0O4—Cl1—O2108.8 (3)
O1—C1—C1i105.6 (3)O3—Cl1—O2101.7 (4)
O1—C1—H1A110.6C10—O6—H6A109.5
C1i—C1—H1A110.6O6—C10—H10A109.5
O1—C1—H1B110.6O6—C10—H10B109.5
C1i—C1—H1B110.6H10A—C10—H10B109.5
H1A—C1—H1B108.7O6—C10—H10C109.5
C3—C2—O1119.5 (4)H10A—C10—H10C109.5
C3—C2—C7121.1 (4)H10B—C10—H10C109.5
O1—C2—C7119.4 (4)
N1i—Ni1—S1—C9169.64 (17)Ni1—N1—N2—C97.8 (5)
N1—Ni1—S1—C98.07 (17)C2—O1—C1—C1i111.8 (4)
O1—Ni1—S1—C939.7 (3)Ni1—O1—C1—C1i42.8 (5)
O1i—Ni1—S1—C985.69 (16)C1—O1—C2—C359.9 (5)
S1i—Ni1—S1—C9104.67 (15)Ni1—O1—C2—C3148.0 (4)
N1i—Ni1—O1—C2140.8 (3)C1—O1—C2—C7121.0 (4)
N1—Ni1—O1—C241.0 (3)Ni1—O1—C2—C731.2 (5)
O1i—Ni1—O1—C2136.9 (3)O1—C2—C3—C4178.7 (5)
S1i—Ni1—O1—C256.4 (3)C7—C2—C3—C40.5 (8)
S1—Ni1—O1—C288.9 (4)C2—C3—C4—C51.2 (9)
N1i—Ni1—O1—C166.4 (3)C3—C4—C5—C62.1 (10)
N1—Ni1—O1—C1111.8 (3)C4—C5—C6—C71.2 (10)
O1i—Ni1—O1—C115.9 (2)C3—C2—C7—C61.3 (7)
S1i—Ni1—O1—C1150.8 (3)O1—C2—C7—C6177.8 (4)
S1—Ni1—O1—C163.9 (4)C3—C2—C7—C8174.7 (5)
N1i—Ni1—N1—C865.6 (4)O1—C2—C7—C86.2 (7)
O1—Ni1—N1—C828.3 (4)C5—C6—C7—C20.5 (8)
O1i—Ni1—N1—C8102.6 (4)C5—C6—C7—C8175.8 (5)
S1i—Ni1—N1—C863.6 (4)N2—N1—C8—C7179.8 (4)
S1—Ni1—N1—C8165.0 (4)Ni1—N1—C8—C75.5 (7)
N1i—Ni1—N1—N2119.8 (3)C2—C7—C8—N121.8 (7)
O1—Ni1—N1—N2157.0 (3)C6—C7—C8—N1162.2 (5)
O1i—Ni1—N1—N282.7 (3)N1—N2—C9—N3179.1 (4)
S1i—Ni1—N1—N2111.0 (3)N1—N2—C9—S11.2 (5)
S1—Ni1—N1—N29.7 (3)Ni1—S1—C9—N3172.8 (4)
C8—N1—N2—C9167.5 (4)Ni1—S1—C9—N27.5 (4)
Symmetry code: (i) x+1, y+1/2, z.
 

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