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The title crystal structure, [Co(NO3)(C10H15N3OS)2]NO3, consists of CoII complex cations and NO3 anions, located on different twofold axes and linked to each other via O—H...O hydrogen bonding. The CoII complex assumes a distorted octa­hedral coordination geometry, formed by a chelating nitrate and two ImTh mol­ecules (ImTh is 1-hydr­oxy-4,4,5,5-tetra­methyl-2-(1,3-thia­zol-2-yl)-4,5-dihydro-1H-imidazole). Within the ImTh mol­ecule, the N—O bond distance of 1.386 (2) Å is much longer than the N—O bonds found in related complexes with the nitroxide radical.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805031508/xu6046sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805031508/xu6046Isup2.hkl
Contains datablock I

CCDC reference: 289940

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.078
  • Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N4
Alert level C PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.86 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Co1 - O3 .. 6.87 su PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N5 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
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 27.50 From the CIF: _reflns_number_total 3326 Count of symmetry unique reflns 1941 Completeness (_total/calc) 171.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1385 Fraction of Friedel pairs measured 0.714 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker 2002); cell refinement: SAINT (Bruker 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.

Bis[1-hydroxy-4,4,5,5-tetramethyl-2-(1,3-thiazol-2-yl)-4,5-dihydro- 1H-imidazole]nitratocobalt(II) nitrate top
Crystal data top
[Co(NO3)(C10H15N3OS)2]NO3F(000) = 658
Mr = 633.59Dx = 1.428 Mg m3
Orthorhombic, P21212Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2 2abCell parameters from 5723 reflections
a = 13.1701 (8) Åθ = 2.5–25.9°
b = 10.4625 (6) ŵ = 0.78 mm1
c = 10.6961 (7) ÅT = 295 K
V = 1473.84 (16) Å3Platelet, red
Z = 20.31 × 0.23 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3326 independent reflections
Radiation source: fine-focus sealed tube2897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1617
Tmin = 0.797, Tmax = 0.925k = 1313
13046 measured reflectionsl = 1313
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.028H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0407P)2 + 0.1802P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3326 reflectionsΔρmax = 0.17 e Å3
184 parametersΔρmin = 0.16 e Å3
1 restraintAbsolute structure: Flack (1983), 1385 Friedel Pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.019 (15)
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
Co10.50000.00000.61307 (3)0.04512 (11)
S10.76523 (5)0.26580 (6)0.67972 (6)0.05813 (17)
O10.82469 (12)0.07507 (17)0.87215 (16)0.0595 (4)
H1'0.88170.07240.84150.089*
O20.50000.00000.2587 (3)0.170 (2)
O30.43059 (16)0.0532 (2)0.43450 (19)0.0779 (6)
O40.42685 (15)0.5457 (2)0.39347 (19)0.0760 (5)
O50.50000.50000.2180 (2)0.0766 (7)
N10.59752 (13)0.16434 (17)0.61430 (18)0.0483 (4)
N20.61427 (14)0.06220 (18)0.73083 (17)0.0467 (4)
N30.76417 (12)0.01760 (18)0.81716 (16)0.0470 (4)
N40.50000.00000.3715 (3)0.0887 (11)
N50.50000.50000.3371 (3)0.0565 (6)
C10.6851 (2)0.3507 (2)0.5866 (2)0.0619 (6)
H10.69810.43260.55710.074*
C20.60040 (19)0.2834 (2)0.5614 (2)0.0581 (6)
H20.54810.31520.51210.070*
C30.67997 (15)0.1437 (2)0.6803 (2)0.0438 (4)
C40.68644 (14)0.0210 (2)0.74420 (17)0.0411 (4)
C50.64501 (17)0.1795 (2)0.8029 (2)0.0515 (5)
C60.72717 (18)0.1253 (2)0.8956 (2)0.0545 (5)
C70.6930 (3)0.2728 (3)0.7071 (3)0.0782 (8)
H7A0.75380.23560.67340.117*
H7B0.70930.35180.74790.117*
H7C0.64570.28860.64060.117*
C80.5551 (2)0.2421 (3)0.8643 (3)0.0754 (8)
H8A0.51420.28320.80190.113*
H8B0.57840.30450.92350.113*
H8C0.51540.17850.90670.113*
C90.8121 (2)0.2116 (3)0.9327 (3)0.0779 (8)
H9A0.85880.16580.98510.117*
H9B0.78540.28360.97770.117*
H9C0.84680.24110.85920.117*
C100.6757 (3)0.0691 (3)1.0141 (2)0.0729 (7)
H10A0.62370.00990.98960.109*
H10B0.64600.13711.06200.109*
H10C0.72560.02571.06380.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.03383 (17)0.0552 (2)0.0463 (2)0.00126 (19)0.0000.000
S10.0619 (4)0.0530 (3)0.0594 (3)0.0153 (3)0.0044 (3)0.0072 (3)
O10.0477 (9)0.0699 (10)0.0607 (10)0.0096 (8)0.0059 (8)0.0015 (8)
O20.217 (5)0.247 (6)0.0462 (17)0.056 (6)0.0000.000
O30.0741 (12)0.0933 (15)0.0662 (11)0.0332 (11)0.0109 (9)0.0022 (10)
O40.0644 (11)0.0898 (14)0.0737 (12)0.0114 (10)0.0080 (10)0.0057 (10)
O50.0445 (11)0.125 (2)0.0602 (14)0.0029 (17)0.0000.000
N10.0398 (9)0.0536 (10)0.0516 (10)0.0007 (7)0.0021 (8)0.0128 (9)
N20.0405 (9)0.0496 (10)0.0500 (10)0.0029 (8)0.0025 (8)0.0118 (8)
N30.0378 (8)0.0539 (10)0.0494 (9)0.0044 (8)0.0047 (7)0.0071 (9)
N40.106 (3)0.108 (3)0.0527 (18)0.033 (3)0.0000.000
N50.0495 (14)0.0587 (15)0.0614 (15)0.0085 (16)0.0000.000
C10.0739 (17)0.0482 (12)0.0636 (15)0.0013 (12)0.0054 (12)0.0116 (11)
C20.0564 (14)0.0569 (14)0.0612 (14)0.0106 (11)0.0048 (11)0.0183 (11)
C30.0403 (11)0.0497 (11)0.0413 (10)0.0021 (9)0.0042 (9)0.0028 (9)
C40.0356 (9)0.0489 (12)0.0389 (9)0.0025 (9)0.0030 (7)0.0037 (9)
C50.0467 (12)0.0497 (12)0.0580 (13)0.0013 (9)0.0034 (10)0.0154 (10)
C60.0551 (13)0.0544 (12)0.0540 (12)0.0005 (10)0.0074 (11)0.0140 (11)
C70.101 (2)0.0622 (17)0.0712 (18)0.0083 (16)0.0070 (16)0.0021 (14)
C80.0635 (16)0.0777 (18)0.0849 (19)0.0196 (14)0.0070 (14)0.0327 (16)
C90.0634 (16)0.0722 (17)0.098 (2)0.0068 (14)0.0162 (15)0.0237 (16)
C100.088 (2)0.0812 (18)0.0495 (14)0.0023 (16)0.0061 (13)0.0105 (13)
Geometric parameters (Å, º) top
Co1—N12.1461 (18)C1—C21.346 (4)
Co1—N22.0676 (18)C1—H10.9300
Co1—O32.1894 (19)C2—H20.9300
Co1—N1i2.1461 (18)C3—C41.457 (3)
Co1—N2i2.0676 (18)C5—C81.505 (3)
Co1—O3i2.1895 (19)C5—C71.550 (4)
S1—C31.701 (2)C5—C61.573 (3)
S1—C11.701 (3)C6—C91.491 (4)
O1—N31.386 (2)C6—C101.553 (4)
O1—H1'0.8200C7—H7A0.9600
O2—N41.207 (4)C7—H7B0.9600
O3—N41.265 (2)C7—H7C0.9600
O4—N51.233 (2)C8—H8A0.9600
O5—N51.274 (3)C8—H8B0.9600
N1—C31.313 (3)C8—H8C0.9600
N1—C21.368 (3)C9—H9A0.9600
N2—C41.297 (3)C9—H9B0.9600
N2—C51.504 (3)C9—H9C0.9600
N3—C41.349 (2)C10—H10A0.9600
N3—C61.487 (3)C10—H10B0.9600
N4—O3i1.265 (2)C10—H10C0.9600
N5—O4ii1.233 (2)
N1—Co1—N1i179.30 (11)C4—C3—S1128.68 (15)
N1—Co1—N279.21 (7)N2—C4—N3114.76 (18)
N1—Co1—N2i100.35 (7)N2—C4—C3119.80 (17)
N1—Co1—O392.95 (8)N3—C4—C3125.42 (17)
N1—Co1—O3i87.67 (8)N2—C5—C8111.54 (19)
N2i—Co1—N2104.94 (10)N2—C5—C7106.55 (19)
N2i—Co1—O398.48 (8)C8—C5—C7109.6 (2)
N2—Co1—O3156.26 (7)N2—C5—C6102.39 (17)
O3—Co1—O3i58.53 (11)C8—C5—C6115.0 (2)
N1i—Co1—O387.67 (8)C7—C5—C6111.3 (2)
N2i—Co1—O3i156.26 (7)N3—C6—C9111.3 (2)
N2—Co1—O3i98.48 (8)N3—C6—C10108.4 (2)
N2i—Co1—N1i79.21 (7)C9—C6—C10109.8 (2)
N2—Co1—N1i100.35 (7)N3—C6—C598.20 (17)
N1i—Co1—O3i92.95 (8)C9—C6—C5117.8 (2)
C3—S1—C189.11 (12)C10—C6—C5110.5 (2)
N3—O1—H1'109.5C5—C7—H7A109.5
N4—O3—Co192.93 (16)C5—C7—H7B109.5
C3—N1—C2110.41 (19)H7A—C7—H7B109.5
C3—N1—Co1111.51 (14)C5—C7—H7C109.5
C2—N1—Co1138.01 (16)H7A—C7—H7C109.5
C4—N2—C5107.08 (17)H7B—C7—H7C109.5
C4—N2—Co1112.91 (14)C5—C8—H8A109.5
C5—N2—Co1139.88 (14)C5—C8—H8B109.5
C4—N3—O1118.18 (18)H8A—C8—H8B109.5
C4—N3—C6107.73 (16)C5—C8—H8C109.5
O1—N3—C6118.63 (17)H8A—C8—H8C109.5
O2—N4—O3122.19 (14)H8B—C8—H8C109.5
O2—N4—O3i122.19 (14)C6—C9—H9A109.5
O3—N4—O3i115.6 (3)C6—C9—H9B109.5
O4—N5—O4ii121.5 (3)H9A—C9—H9B109.5
O4—N5—O5119.26 (15)C6—C9—H9C109.5
O4ii—N5—O5119.25 (15)H9A—C9—H9C109.5
C2—C1—S1110.99 (19)H9B—C9—H9C109.5
C2—C1—H1124.5C6—C10—H10A109.5
S1—C1—H1124.5C6—C10—H10B109.5
C1—C2—N1114.6 (2)H10A—C10—H10B109.5
C1—C2—H2122.7C6—C10—H10C109.5
N1—C2—H2122.7H10A—C10—H10C109.5
N1—C3—C4116.45 (17)H10B—C10—H10C109.5
N1—C3—S1114.87 (16)
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O5iii0.821.852.6227 (19)158
Symmetry code: (iii) x+3/2, y1/2, z+1.
 

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