The title crystal structure, [Co(NO
3)(C
10H
15N
3OS)
2]NO
3, consists of Co
II complex cations and NO
3− anions, located on different twofold axes and linked to each other
via O—H
O hydrogen bonding. The Co
II 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-1
H-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
CCDC reference: 289940
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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-
1
H-imidazole]nitratocobalt(II) nitrate
top
Crystal data top
[Co(NO3)(C10H15N3OS)2]NO3 | F(000) = 658 |
Mr = 633.59 | Dx = 1.428 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 5723 reflections |
a = 13.1701 (8) Å | θ = 2.5–25.9° |
b = 10.4625 (6) Å | µ = 0.78 mm−1 |
c = 10.6961 (7) Å | T = 295 K |
V = 1473.84 (16) Å3 | Platelet, red |
Z = 2 | 0.31 × 0.23 × 0.10 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3326 independent reflections |
Radiation source: fine-focus sealed tube | 2897 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
φ and ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→17 |
Tmin = 0.797, Tmax = 0.925 | k = −13→13 |
13046 measured reflections | l = −13→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.028 | H-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 reflections | Δρmax = 0.17 e Å−3 |
184 parameters | Δρmin = −0.16 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1385 Friedel Pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Co1 | 0.5000 | 0.0000 | 0.61307 (3) | 0.04512 (11) | |
S1 | 0.76523 (5) | −0.26580 (6) | 0.67972 (6) | 0.05813 (17) | |
O1 | 0.82469 (12) | −0.07507 (17) | 0.87215 (16) | 0.0595 (4) | |
H1' | 0.8817 | −0.0724 | 0.8415 | 0.089* | |
O2 | 0.5000 | 0.0000 | 0.2587 (3) | 0.170 (2) | |
O3 | 0.43059 (16) | −0.0532 (2) | 0.43450 (19) | 0.0779 (6) | |
O4 | 0.42685 (15) | 0.5457 (2) | 0.39347 (19) | 0.0760 (5) | |
O5 | 0.5000 | 0.5000 | 0.2180 (2) | 0.0766 (7) | |
N1 | 0.59752 (13) | −0.16434 (17) | 0.61430 (18) | 0.0483 (4) | |
N2 | 0.61427 (14) | 0.06220 (18) | 0.73083 (17) | 0.0467 (4) | |
N3 | 0.76417 (12) | 0.01760 (18) | 0.81716 (16) | 0.0470 (4) | |
N4 | 0.5000 | 0.0000 | 0.3715 (3) | 0.0887 (11) | |
N5 | 0.5000 | 0.5000 | 0.3371 (3) | 0.0565 (6) | |
C1 | 0.6851 (2) | −0.3507 (2) | 0.5866 (2) | 0.0619 (6) | |
H1 | 0.6981 | −0.4326 | 0.5571 | 0.074* | |
C2 | 0.60040 (19) | −0.2834 (2) | 0.5614 (2) | 0.0581 (6) | |
H2 | 0.5481 | −0.3152 | 0.5121 | 0.070* | |
C3 | 0.67997 (15) | −0.1437 (2) | 0.6803 (2) | 0.0438 (4) | |
C4 | 0.68644 (14) | −0.0210 (2) | 0.74420 (17) | 0.0411 (4) | |
C5 | 0.64501 (17) | 0.1795 (2) | 0.8029 (2) | 0.0515 (5) | |
C6 | 0.72717 (18) | 0.1253 (2) | 0.8956 (2) | 0.0545 (5) | |
C7 | 0.6930 (3) | 0.2728 (3) | 0.7071 (3) | 0.0782 (8) | |
H7A | 0.7538 | 0.2356 | 0.6734 | 0.117* | |
H7B | 0.7093 | 0.3518 | 0.7479 | 0.117* | |
H7C | 0.6457 | 0.2886 | 0.6406 | 0.117* | |
C8 | 0.5551 (2) | 0.2421 (3) | 0.8643 (3) | 0.0754 (8) | |
H8A | 0.5142 | 0.2832 | 0.8019 | 0.113* | |
H8B | 0.5784 | 0.3045 | 0.9235 | 0.113* | |
H8C | 0.5154 | 0.1785 | 0.9067 | 0.113* | |
C9 | 0.8121 (2) | 0.2116 (3) | 0.9327 (3) | 0.0779 (8) | |
H9A | 0.8588 | 0.1658 | 0.9851 | 0.117* | |
H9B | 0.7854 | 0.2836 | 0.9777 | 0.117* | |
H9C | 0.8468 | 0.2411 | 0.8592 | 0.117* | |
C10 | 0.6757 (3) | 0.0691 (3) | 1.0141 (2) | 0.0729 (7) | |
H10A | 0.6237 | 0.0099 | 0.9896 | 0.109* | |
H10B | 0.6460 | 0.1371 | 1.0620 | 0.109* | |
H10C | 0.7256 | 0.0257 | 1.0638 | 0.109* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Co1 | 0.03383 (17) | 0.0552 (2) | 0.0463 (2) | −0.00126 (19) | 0.000 | 0.000 |
S1 | 0.0619 (4) | 0.0530 (3) | 0.0594 (3) | 0.0153 (3) | −0.0044 (3) | −0.0072 (3) |
O1 | 0.0477 (9) | 0.0699 (10) | 0.0607 (10) | 0.0096 (8) | −0.0059 (8) | 0.0015 (8) |
O2 | 0.217 (5) | 0.247 (6) | 0.0462 (17) | −0.056 (6) | 0.000 | 0.000 |
O3 | 0.0741 (12) | 0.0933 (15) | 0.0662 (11) | −0.0332 (11) | −0.0109 (9) | −0.0022 (10) |
O4 | 0.0644 (11) | 0.0898 (14) | 0.0737 (12) | 0.0114 (10) | 0.0080 (10) | −0.0057 (10) |
O5 | 0.0445 (11) | 0.125 (2) | 0.0602 (14) | −0.0029 (17) | 0.000 | 0.000 |
N1 | 0.0398 (9) | 0.0536 (10) | 0.0516 (10) | −0.0007 (7) | 0.0021 (8) | −0.0128 (9) |
N2 | 0.0405 (9) | 0.0496 (10) | 0.0500 (10) | 0.0029 (8) | −0.0025 (8) | −0.0118 (8) |
N3 | 0.0378 (8) | 0.0539 (10) | 0.0494 (9) | 0.0044 (8) | −0.0047 (7) | −0.0071 (9) |
N4 | 0.106 (3) | 0.108 (3) | 0.0527 (18) | −0.033 (3) | 0.000 | 0.000 |
N5 | 0.0495 (14) | 0.0587 (15) | 0.0614 (15) | −0.0085 (16) | 0.000 | 0.000 |
C1 | 0.0739 (17) | 0.0482 (12) | 0.0636 (15) | 0.0013 (12) | 0.0054 (12) | −0.0116 (11) |
C2 | 0.0564 (14) | 0.0569 (14) | 0.0612 (14) | −0.0106 (11) | 0.0048 (11) | −0.0183 (11) |
C3 | 0.0403 (11) | 0.0497 (11) | 0.0413 (10) | 0.0021 (9) | 0.0042 (9) | −0.0028 (9) |
C4 | 0.0356 (9) | 0.0489 (12) | 0.0389 (9) | 0.0025 (9) | 0.0030 (7) | −0.0037 (9) |
C5 | 0.0467 (12) | 0.0497 (12) | 0.0580 (13) | 0.0013 (9) | −0.0034 (10) | −0.0154 (10) |
C6 | 0.0551 (13) | 0.0544 (12) | 0.0540 (12) | 0.0005 (10) | −0.0074 (11) | −0.0140 (11) |
C7 | 0.101 (2) | 0.0622 (17) | 0.0712 (18) | −0.0083 (16) | −0.0070 (16) | 0.0021 (14) |
C8 | 0.0635 (16) | 0.0777 (18) | 0.0849 (19) | 0.0196 (14) | −0.0070 (14) | −0.0327 (16) |
C9 | 0.0634 (16) | 0.0722 (17) | 0.098 (2) | −0.0068 (14) | −0.0162 (15) | −0.0237 (16) |
C10 | 0.088 (2) | 0.0812 (18) | 0.0495 (14) | 0.0023 (16) | 0.0061 (13) | −0.0105 (13) |
Geometric parameters (Å, º) top
Co1—N1 | 2.1461 (18) | C1—C2 | 1.346 (4) |
Co1—N2 | 2.0676 (18) | C1—H1 | 0.9300 |
Co1—O3 | 2.1894 (19) | C2—H2 | 0.9300 |
Co1—N1i | 2.1461 (18) | C3—C4 | 1.457 (3) |
Co1—N2i | 2.0676 (18) | C5—C8 | 1.505 (3) |
Co1—O3i | 2.1895 (19) | C5—C7 | 1.550 (4) |
S1—C3 | 1.701 (2) | C5—C6 | 1.573 (3) |
S1—C1 | 1.701 (3) | C6—C9 | 1.491 (4) |
O1—N3 | 1.386 (2) | C6—C10 | 1.553 (4) |
O1—H1' | 0.8200 | C7—H7A | 0.9600 |
O2—N4 | 1.207 (4) | C7—H7B | 0.9600 |
O3—N4 | 1.265 (2) | C7—H7C | 0.9600 |
O4—N5 | 1.233 (2) | C8—H8A | 0.9600 |
O5—N5 | 1.274 (3) | C8—H8B | 0.9600 |
N1—C3 | 1.313 (3) | C8—H8C | 0.9600 |
N1—C2 | 1.368 (3) | C9—H9A | 0.9600 |
N2—C4 | 1.297 (3) | C9—H9B | 0.9600 |
N2—C5 | 1.504 (3) | C9—H9C | 0.9600 |
N3—C4 | 1.349 (2) | C10—H10A | 0.9600 |
N3—C6 | 1.487 (3) | C10—H10B | 0.9600 |
N4—O3i | 1.265 (2) | C10—H10C | 0.9600 |
N5—O4ii | 1.233 (2) | | |
| | | |
N1—Co1—N1i | 179.30 (11) | C4—C3—S1 | 128.68 (15) |
N1—Co1—N2 | 79.21 (7) | N2—C4—N3 | 114.76 (18) |
N1—Co1—N2i | 100.35 (7) | N2—C4—C3 | 119.80 (17) |
N1—Co1—O3 | 92.95 (8) | N3—C4—C3 | 125.42 (17) |
N1—Co1—O3i | 87.67 (8) | N2—C5—C8 | 111.54 (19) |
N2i—Co1—N2 | 104.94 (10) | N2—C5—C7 | 106.55 (19) |
N2i—Co1—O3 | 98.48 (8) | C8—C5—C7 | 109.6 (2) |
N2—Co1—O3 | 156.26 (7) | N2—C5—C6 | 102.39 (17) |
O3—Co1—O3i | 58.53 (11) | C8—C5—C6 | 115.0 (2) |
N1i—Co1—O3 | 87.67 (8) | C7—C5—C6 | 111.3 (2) |
N2i—Co1—O3i | 156.26 (7) | N3—C6—C9 | 111.3 (2) |
N2—Co1—O3i | 98.48 (8) | N3—C6—C10 | 108.4 (2) |
N2i—Co1—N1i | 79.21 (7) | C9—C6—C10 | 109.8 (2) |
N2—Co1—N1i | 100.35 (7) | N3—C6—C5 | 98.20 (17) |
N1i—Co1—O3i | 92.95 (8) | C9—C6—C5 | 117.8 (2) |
C3—S1—C1 | 89.11 (12) | C10—C6—C5 | 110.5 (2) |
N3—O1—H1' | 109.5 | C5—C7—H7A | 109.5 |
N4—O3—Co1 | 92.93 (16) | C5—C7—H7B | 109.5 |
C3—N1—C2 | 110.41 (19) | H7A—C7—H7B | 109.5 |
C3—N1—Co1 | 111.51 (14) | C5—C7—H7C | 109.5 |
C2—N1—Co1 | 138.01 (16) | H7A—C7—H7C | 109.5 |
C4—N2—C5 | 107.08 (17) | H7B—C7—H7C | 109.5 |
C4—N2—Co1 | 112.91 (14) | C5—C8—H8A | 109.5 |
C5—N2—Co1 | 139.88 (14) | C5—C8—H8B | 109.5 |
C4—N3—O1 | 118.18 (18) | H8A—C8—H8B | 109.5 |
C4—N3—C6 | 107.73 (16) | C5—C8—H8C | 109.5 |
O1—N3—C6 | 118.63 (17) | H8A—C8—H8C | 109.5 |
O2—N4—O3 | 122.19 (14) | H8B—C8—H8C | 109.5 |
O2—N4—O3i | 122.19 (14) | C6—C9—H9A | 109.5 |
O3—N4—O3i | 115.6 (3) | C6—C9—H9B | 109.5 |
O4—N5—O4ii | 121.5 (3) | H9A—C9—H9B | 109.5 |
O4—N5—O5 | 119.26 (15) | C6—C9—H9C | 109.5 |
O4ii—N5—O5 | 119.25 (15) | H9A—C9—H9C | 109.5 |
C2—C1—S1 | 110.99 (19) | H9B—C9—H9C | 109.5 |
C2—C1—H1 | 124.5 | C6—C10—H10A | 109.5 |
S1—C1—H1 | 124.5 | C6—C10—H10B | 109.5 |
C1—C2—N1 | 114.6 (2) | H10A—C10—H10B | 109.5 |
C1—C2—H2 | 122.7 | C6—C10—H10C | 109.5 |
N1—C2—H2 | 122.7 | H10A—C10—H10C | 109.5 |
N1—C3—C4 | 116.45 (17) | H10B—C10—H10C | 109.5 |
N1—C3—S1 | 114.87 (16) | | |
Symmetry codes: (i) −x+1, −y, z; (ii) −x+1, −y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1′···O5iii | 0.82 | 1.85 | 2.6227 (19) | 158 |
Symmetry code: (iii) −x+3/2, y−1/2, −z+1. |