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The crystal stucture of the title compound, [Ni(C8H4O4)(C6H6N4S2)2]·3.5H2O, consists of a nickel(II) complex and water of crystallization. The complex assumes an octahedral geometry formed by one phthalate dianion and two di­amino­bi­thia­zole mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803024516/om6188sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803024516/om6188Isup2.hkl
Contains datablock I

CCDC reference: 227738

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.006 Å
  • H-atom completeness 87%
  • Disorder in solvent or counterion
  • R factor = 0.045
  • wR factor = 0.112
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)... ? PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C16 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C13 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 30.00 Perc. PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S3 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S4 in Main Residue . ?
Alert level G FORMU01_ALERT_2_G There is a discrepancy between the atom counts in the _chemical_formula_sum and the formula from the _atom_site* data. Atom count from _chemical_formula_sum:C20 H23 N8 Ni1 O7.5 S4 Atom count from the _atom_site data: C20 H20 N8 Ni1 O7.5 S4 CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected. CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional? From the CIF: _cell_formula_units_Z 4 From the CIF: _chemical_formula_sum C20 H23 N8 Ni O7.5 S4 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.00 0.00 H 92.00 80.00 12.00 N 32.00 32.00 0.00 Ni 4.00 4.00 0.00 O 30.00 30.00 0.00 S 16.00 16.00 0.00
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(I) top
Crystal data top
[Ni(C8H4O4)(C6H6N4S2)2]·3.5H2OF(000) = 1404
Mr = 682.41Dx = 1.616 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 16667 reflections
a = 14.5564 (14) Åθ = 2.0–24.0°
b = 13.5072 (12) ŵ = 1.05 mm1
c = 15.7929 (11) ÅT = 295 K
β = 115.430 (12)°Prism, green
V = 2804.3 (5) Å30.34 × 0.27 × 0.11 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
6343 independent reflections
Radiation source: fine-focus sealed tube4886 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 10.00 pixels mm-1θmax = 27.4°, θmin = 1.6°
ω scansh = 1818
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1517
Tmin = 0.698, Tmax = 0.890l = 2020
25568 measured reflections
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0519P)2 + 2.0505P]
where P = (Fo2 + 2Fc2)/3
6343 reflections(Δ/σ)max = 0.001
379 parametersΔρmax = 0.42 e Å3
0 restraintsΔρmin = 0.31 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*/UeqOcc. (<1)
Ni0.35883 (3)0.51898 (2)0.19229 (2)0.03649 (10)
S10.64997 (6)0.41821 (7)0.45561 (5)0.0593 (2)
S20.58129 (7)0.62203 (7)0.06734 (6)0.0640 (2)
S30.05305 (8)0.62300 (9)0.04953 (7)0.0783 (3)
S40.29566 (9)0.21083 (7)0.04495 (8)0.0753 (3)
O10.27935 (16)0.48447 (16)0.27154 (14)0.0536 (5)
O20.1438 (3)0.4485 (3)0.2919 (3)0.1164 (13)
O30.38003 (16)0.65945 (15)0.25088 (13)0.0487 (5)
O40.42141 (16)0.68861 (17)0.40102 (13)0.0550 (5)
N10.49585 (18)0.47117 (17)0.30461 (15)0.0421 (5)
N20.4525 (2)0.4059 (2)0.42066 (17)0.0585 (7)
H2A0.38860.41250.38550.070*
H2B0.47280.38180.47620.070*
N30.46713 (18)0.55879 (16)0.14280 (15)0.0410 (5)
N40.3803 (2)0.6455 (2)0.00120 (18)0.0643 (8)
H4A0.32220.63740.00220.077*
H4B0.38440.67730.04420.077*
N50.22520 (18)0.55889 (18)0.07300 (15)0.0446 (5)
N60.2022 (3)0.7296 (2)0.0817 (2)0.0694 (8)
H6A0.26250.73670.12580.083*
H6B0.16290.78020.06100.083*
N70.31788 (18)0.38277 (17)0.12080 (16)0.0433 (5)
N80.4416 (2)0.2674 (2)0.2112 (2)0.0653 (7)
H8A0.46990.30890.25630.078*
H8B0.46580.20850.21590.078*
C10.5200 (2)0.4331 (2)0.38936 (18)0.0441 (6)
C20.6708 (3)0.4646 (2)0.3631 (2)0.0568 (8)
H20.73450.47180.36350.068*
C30.5829 (2)0.4885 (2)0.2912 (2)0.0440 (6)
C40.4641 (2)0.6086 (2)0.07003 (19)0.0459 (6)
C50.6371 (3)0.5603 (2)0.1726 (3)0.0596 (8)
H50.70630.54720.20470.072*
C60.5665 (2)0.53359 (19)0.2019 (2)0.0433 (6)
C70.1697 (2)0.6402 (2)0.0453 (2)0.0520 (7)
C80.0831 (3)0.5010 (3)0.0525 (3)0.0763 (11)
H80.04100.45540.09600.092*
C90.1756 (2)0.4793 (2)0.0160 (2)0.0528 (7)
C100.3599 (2)0.2944 (2)0.1338 (2)0.0497 (7)
C110.2078 (3)0.3005 (3)0.0116 (3)0.0752 (11)
H110.15190.29180.06910.090*
C120.2301 (2)0.3857 (2)0.0381 (2)0.0516 (7)
C130.2011 (2)0.5104 (3)0.2807 (2)0.0603 (9)
C140.1758 (2)0.6175 (3)0.2791 (2)0.0601 (9)
C150.0753 (3)0.6452 (4)0.2597 (3)0.0861 (14)
H150.02730.59630.25160.103*
C160.0470 (4)0.7434 (5)0.2526 (3)0.1051 (19)
H160.02020.76000.23810.126*
C170.1175 (4)0.8171 (4)0.2670 (3)0.0922 (15)
H170.09790.88320.26130.111*
C180.2173 (3)0.7924 (3)0.2899 (2)0.0693 (10)
H180.26530.84230.30150.083*
C190.2470 (2)0.6935 (3)0.29595 (19)0.0522 (7)
C200.3580 (2)0.6764 (2)0.31963 (19)0.0439 (6)
O1W0.0814 (4)0.4634 (4)0.4353 (4)0.1582 (18)
O2W0.1991 (3)0.2625 (3)0.2503 (4)0.1564 (19)
O3W0.1213 (5)0.1096 (6)0.1473 (5)0.119 (2)0.50
O41W0.0790 (7)0.8949 (7)0.0347 (9)0.159 (5)0.50
O42W0.0059 (8)0.8461 (6)0.0331 (8)0.139 (3)0.50
H11W0.12590.47070.41050.100*
H12W0.02350.49770.40120.100*
H21W0.21390.32100.23860.100*
H22W0.16980.23500.19290.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni0.04375 (19)0.03802 (18)0.03103 (16)0.00091 (15)0.01921 (14)0.00027 (13)
S10.0541 (5)0.0728 (6)0.0462 (4)0.0094 (4)0.0169 (3)0.0136 (4)
S20.0779 (6)0.0647 (5)0.0731 (5)0.0025 (4)0.0549 (5)0.0164 (4)
S30.0600 (6)0.0983 (8)0.0650 (5)0.0187 (5)0.0160 (4)0.0241 (5)
S40.0999 (8)0.0450 (5)0.0844 (6)0.0119 (5)0.0427 (6)0.0195 (4)
O10.0510 (12)0.0694 (14)0.0483 (11)0.0035 (10)0.0288 (10)0.0075 (10)
O20.111 (3)0.108 (2)0.185 (4)0.053 (2)0.116 (3)0.056 (2)
O30.0594 (12)0.0486 (11)0.0471 (10)0.0084 (9)0.0314 (10)0.0129 (9)
O40.0549 (13)0.0684 (14)0.0373 (10)0.0006 (10)0.0156 (9)0.0060 (9)
N10.0482 (13)0.0464 (13)0.0339 (11)0.0003 (10)0.0198 (10)0.0032 (10)
N20.0581 (16)0.0807 (19)0.0387 (12)0.0005 (14)0.0227 (12)0.0134 (13)
N30.0541 (14)0.0392 (12)0.0372 (11)0.0019 (10)0.0268 (10)0.0017 (9)
N40.0682 (18)0.083 (2)0.0479 (14)0.0033 (15)0.0303 (14)0.0238 (14)
N50.0499 (14)0.0476 (13)0.0368 (11)0.0037 (11)0.0192 (10)0.0017 (10)
N60.092 (2)0.0536 (17)0.0646 (17)0.0211 (16)0.0357 (16)0.0075 (14)
N70.0496 (13)0.0410 (12)0.0445 (12)0.0044 (10)0.0252 (11)0.0023 (10)
N80.075 (2)0.0459 (15)0.0744 (19)0.0136 (14)0.0317 (16)0.0003 (13)
C10.0495 (16)0.0448 (15)0.0364 (13)0.0003 (13)0.0171 (12)0.0025 (12)
C20.0518 (18)0.064 (2)0.0586 (18)0.0053 (15)0.0269 (15)0.0113 (15)
C30.0497 (16)0.0401 (14)0.0472 (15)0.0010 (12)0.0256 (13)0.0003 (12)
C40.0641 (18)0.0416 (15)0.0431 (14)0.0028 (13)0.0335 (14)0.0009 (12)
C50.0577 (19)0.0592 (19)0.075 (2)0.0060 (16)0.0410 (17)0.0140 (17)
C60.0532 (16)0.0375 (14)0.0480 (15)0.0004 (12)0.0302 (13)0.0007 (12)
C70.0617 (19)0.0589 (19)0.0430 (15)0.0112 (15)0.0298 (14)0.0115 (14)
C80.058 (2)0.094 (3)0.055 (2)0.009 (2)0.0039 (16)0.0038 (19)
C90.0536 (18)0.0593 (18)0.0437 (15)0.0064 (15)0.0192 (13)0.0023 (14)
C100.0620 (19)0.0413 (15)0.0585 (17)0.0059 (14)0.0378 (16)0.0041 (13)
C110.082 (3)0.062 (2)0.067 (2)0.0174 (19)0.0180 (19)0.0191 (18)
C120.0529 (17)0.0537 (18)0.0472 (15)0.0103 (14)0.0205 (14)0.0068 (13)
C130.0529 (18)0.086 (2)0.0514 (17)0.0236 (17)0.0317 (15)0.0227 (17)
C140.0470 (17)0.092 (3)0.0424 (15)0.0055 (17)0.0202 (13)0.0224 (16)
C150.050 (2)0.141 (4)0.066 (2)0.006 (2)0.0242 (17)0.041 (3)
C160.060 (3)0.168 (5)0.072 (3)0.038 (3)0.014 (2)0.038 (3)
C170.081 (3)0.116 (4)0.066 (2)0.041 (3)0.019 (2)0.019 (2)
C180.074 (2)0.080 (2)0.0493 (17)0.020 (2)0.0225 (16)0.0114 (17)
C190.0505 (17)0.072 (2)0.0333 (13)0.0056 (15)0.0167 (12)0.0119 (13)
C200.0522 (16)0.0404 (14)0.0422 (14)0.0039 (12)0.0232 (13)0.0060 (12)
O1W0.156 (4)0.197 (5)0.182 (4)0.025 (3)0.130 (4)0.005 (4)
O2W0.153 (4)0.097 (3)0.276 (6)0.003 (3)0.147 (4)0.040 (3)
O3W0.067 (4)0.165 (7)0.115 (5)0.001 (4)0.030 (4)0.019 (5)
O41W0.124 (7)0.111 (6)0.292 (13)0.075 (5)0.136 (8)0.106 (8)
O42W0.180 (9)0.093 (5)0.219 (10)0.033 (6)0.155 (9)0.025 (6)
Geometric parameters (Å, º) top
Ni—O32.0752 (19)N6—H6B0.8600
Ni—O12.0895 (19)N7—C101.316 (4)
Ni—N72.106 (2)N7—C121.381 (4)
Ni—N32.108 (2)N8—C101.340 (4)
Ni—N52.116 (2)N8—H8A0.8600
Ni—N12.122 (2)N8—H8B0.8600
S1—C21.732 (3)C2—C31.336 (4)
S1—C11.736 (3)C2—H20.9300
S2—C51.720 (3)C3—C61.459 (4)
S2—C41.734 (3)C5—C61.345 (4)
S3—C81.711 (5)C5—H50.9300
S3—C71.731 (3)C8—C91.348 (5)
S4—C111.709 (4)C8—H80.9300
S4—C101.729 (3)C9—C121.453 (5)
O1—C131.258 (4)C11—C121.352 (5)
O2—C131.247 (4)C11—H110.9300
O3—C201.278 (3)C13—C141.490 (5)
O4—C201.230 (3)C14—C191.400 (5)
N1—C11.333 (3)C14—C151.410 (5)
N1—C31.391 (4)C15—C161.380 (7)
N2—C11.326 (4)C15—H150.9300
N2—H2A0.8600C16—C171.377 (7)
N2—H2B0.8600C16—H160.9300
N3—C41.316 (3)C17—C181.379 (6)
N3—C61.385 (4)C17—H170.9300
N4—C41.334 (4)C18—C191.396 (5)
N4—H4A0.8600C18—H180.9300
N4—H4B0.8600C19—C201.512 (4)
N5—C71.322 (4)O1W—H11W0.895
N5—C91.390 (4)O1W—H12W0.908
N6—C71.334 (4)O2W—H21W0.860
N6—H6A0.8600O2W—H22W0.901
O3—Ni—O187.22 (8)N3—C4—N4125.4 (3)
O3—Ni—N7172.43 (9)N3—C4—S2114.2 (2)
O1—Ni—N791.39 (9)N4—C4—S2120.4 (2)
O3—Ni—N386.58 (8)C6—C5—S2110.4 (3)
O1—Ni—N3166.81 (9)C6—C5—H5124.8
N7—Ni—N396.24 (9)S2—C5—H5124.8
O3—Ni—N593.89 (9)C5—C6—N3115.7 (3)
O1—Ni—N593.23 (9)C5—C6—C3127.8 (3)
N7—Ni—N578.75 (9)N3—C6—C3116.4 (2)
N3—Ni—N598.79 (9)N5—C7—N6123.8 (3)
O3—Ni—N189.95 (9)N5—C7—S3114.1 (2)
O1—Ni—N189.71 (8)N6—C7—S3121.9 (2)
N7—Ni—N197.49 (9)C9—C8—S3111.5 (3)
N3—Ni—N178.66 (9)C9—C8—H8124.2
N5—Ni—N1175.27 (9)S3—C8—H8124.2
C2—S1—C189.45 (15)C8—C9—N5114.4 (3)
C5—S2—C489.25 (15)C8—C9—C12129.5 (3)
C8—S3—C789.18 (16)N5—C9—C12116.0 (3)
C11—S4—C1089.07 (16)N7—C10—N8124.1 (3)
C13—O1—Ni140.2 (2)N7—C10—S4114.4 (2)
C20—O3—Ni119.91 (18)N8—C10—S4121.4 (2)
C1—N1—C3110.7 (2)C12—C11—S4111.1 (3)
C1—N1—Ni134.8 (2)C12—C11—H11124.4
C3—N1—Ni114.34 (17)S4—C11—H11124.4
C1—N2—H2A120.0C11—C12—N7114.7 (3)
C1—N2—H2B120.0C11—C12—C9129.1 (3)
H2A—N2—H2B120.0N7—C12—C9116.2 (3)
C4—N3—C6110.3 (2)O2—C13—O1121.5 (4)
C4—N3—Ni134.8 (2)O2—C13—C14118.6 (3)
C6—N3—Ni114.71 (16)O1—C13—C14119.9 (3)
C4—N4—H4A120.0C19—C14—C15117.5 (4)
C4—N4—H4B120.0C19—C14—C13123.5 (3)
H4A—N4—H4B120.0C15—C14—C13119.1 (4)
C7—N5—C9110.8 (3)C16—C15—C14121.2 (5)
C7—N5—Ni134.8 (2)C16—C15—H15119.4
C9—N5—Ni113.78 (19)C14—C15—H15119.4
C7—N6—H6A120.0C17—C16—C15120.4 (4)
C7—N6—H6B120.0C17—C16—H16119.8
H6A—N6—H6B120.0C15—C16—H16119.8
C10—N7—C12110.7 (3)C16—C17—C18119.7 (4)
C10—N7—Ni134.7 (2)C16—C17—H17120.2
C12—N7—Ni114.56 (19)C18—C17—H17120.2
C10—N8—H8A120.0C17—C18—C19120.7 (4)
C10—N8—H8B120.0C17—C18—H18119.7
H8A—N8—H8B120.0C19—C18—H18119.7
N2—C1—N1124.3 (3)C18—C19—C14120.5 (3)
N2—C1—S1122.2 (2)C18—C19—C20115.5 (3)
N1—C1—S1113.5 (2)C14—C19—C20124.0 (3)
C3—C2—S1110.7 (2)O4—C20—O3124.2 (3)
C3—C2—H2124.7O4—C20—C19118.8 (2)
S1—C2—H2124.7O3—C20—C19116.7 (2)
C2—C3—N1115.7 (3)H11W—O1W—H12W110.3
C2—C3—C6128.5 (3)H21W—O2W—H22W102.4
N1—C3—C6115.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O10.862.062.816 (3)146
N2—H2B···O4i0.862.122.914 (3)154
N4—H4A···N50.862.393.154 (4)148
N4—H4B···O4ii0.862.172.949 (4)150
N6—H6A···O30.862.242.966 (4)142
N6—H6B···O41W0.861.912.758 (11)171
N6—H6B···O42W0.862.433.197 (12)149
N8—H8A···N10.862.303.062 (4)148
N8—H8B···O3iii0.862.182.808 (4)130
O1W—H11W···O20.902.022.786 (8)143
O1W—H12W···O42Wiv0.912.473.005 (11)118
O1W—H12W···O3Wv0.912.433.317 (10)164
O2W—H21W···O10.862.373.183 (5)157
O2W—H21W···O20.862.332.801 (6)114
O2W—H22W···O3W0.901.862.571 (9)135
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+3/2, z1/2; (iii) x+1, y1/2, z+1/2; (iv) x, y+3/2, z+1/2; (v) x, y+1/2, z+1/2.
 

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