Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029741/xu2277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029741/xu2277Isup2.hkl |
CCDC reference: 654806
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.009 Å
- R factor = 0.055
- wR factor = 0.123
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.82 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S21 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N41 PLAT322_ALERT_2_C Check Hybridisation of S11 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S12 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S21 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S22 in Main Residue . ? PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni (2) 1.95
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 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 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
An ethanol solution (20 ml) containing DABT (0.20 g, 1 mmol) and NiCl2.6H2O (0.24 g, 1 mmol) was mixed with an aqueous solution (10 ml) of 2-nitrobenzoic acid (0.34 g, 2 mmol) and NaOH (0.08 g, 2 mmol). The mixture was refluxed for 6 h. After cooling to room temperature the solution was filtered. Single crystals of the title compound were obtained from the filtrate after 4 d.
H atoms on carbon atoms were placed in calculated positions, with C—H distances = 0.93 Å (aromatic), and were included in the final cycles of refinement in riding mode with Uiso(H) = 1.2Ueq(C). Amino H atoms were located in a difference Fourier map and included in the structure factor calculations with fixed positional and isotropic displacement parameters Uiso(H) = 0.05 Å2.
Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown potential application in the field of soft magnetic material (Liu et al., 2001). As part of serial structural investigation of metal complexes with DABT (Liu & Xu, 2004), the title NiII complex was recently prepared and its X-ray structure is presented here.
The molecular structure of the title compound is shown in Fig. 1. The Ni ion has a distorted octahedral coordinatation geometry formed by one 2-nitrobenzoate anion and two DABT ligands. Within the complex, two DABT moieties are approximately perpendicular to each other with a dihedral angle of 81.23 (7)°. This is comparable to 84.3 (4)° found in a NiII complex of DABT reported previously (Liu & Xu, 2003). Each DABT moiety is approximately coplanar coordinated to Ni atom, the dihedral angles between two thiazole rings being 6.2 (3) and 2.6 (2)°, respectively, which agree with 4.57 (7)° found in [Mn(DABT)(oxydiacetate)] (Luo et al., 2004). The average Ni—N bond distance (Table 1) is shorter than the value of 2.113 (2) Å of average Ni—N bond distance found in reported NiII complex of DABT (Liu & Xu, 2003).
The extensive hydrogen bonding occurs in the crystal structure (Table 2). While 2-nitrobenzoate anion links with complex cation via N—H···O hydrogen bonding, the N—H···O hydrogen bonding is also observed between complex cations. They help to stabilize the crystal structure.
For general background, see Liu et al. (2001); Liu & Xu (2004). For related structures, see Liu & Xu (2003); Luo et al. (2004).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & 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).
Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms), dashed lines showing the hydrogen bonding [symmetry code: (i) x, y, z - 1]. |
[Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4) | F(000) = 1608 |
Mr = 787.47 | Dx = 1.612 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5670 reflections |
a = 15.1514 (18) Å | θ = 2.0–25.0° |
b = 13.5905 (16) Å | µ = 0.92 mm−1 |
c = 16.4702 (19) Å | T = 295 K |
β = 106.901 (2)° | Prism, green |
V = 3245.0 (7) Å3 | 0.20 × 0.17 × 0.14 mm |
Z = 4 |
Rigaku R-AXIS RAPID IP diffractometer | 5721 independent reflections |
Radiation source: fine-focus sealed tube | 3217 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
Detector resolution: 10.0 pixels mm-1 | θmax = 25.0°, θmin = 1.9° |
ω scans | h = −16→18 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −8→16 |
Tmin = 0.812, Tmax = 0.880 | l = −18→19 |
16530 measured reflections |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0399P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
5721 reflections | Δρmax = 0.42 e Å−3 |
443 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0016 (3) |
[Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4) | V = 3245.0 (7) Å3 |
Mr = 787.47 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.1514 (18) Å | µ = 0.92 mm−1 |
b = 13.5905 (16) Å | T = 295 K |
c = 16.4702 (19) Å | 0.20 × 0.17 × 0.14 mm |
β = 106.901 (2)° |
Rigaku R-AXIS RAPID IP diffractometer | 5721 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 3217 reflections with I > 2σ(I) |
Tmin = 0.812, Tmax = 0.880 | Rint = 0.086 |
16530 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.42 e Å−3 |
5721 reflections | Δρmin = −0.37 e Å−3 |
443 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni | 0.63304 (4) | 0.33644 (5) | 0.24108 (4) | 0.0312 (2) | |
N11 | 0.5040 (2) | 0.2921 (3) | 0.1665 (2) | 0.0331 (10) | |
N12 | 0.4906 (3) | 0.1244 (3) | 0.1911 (3) | 0.0561 (13) | |
H12A | 0.4577 | 0.0832 | 0.1957 | 0.050* | |
H12B | 0.5402 | 0.1254 | 0.2291 | 0.050* | |
N13 | 0.5856 (3) | 0.4680 (3) | 0.1795 (2) | 0.0360 (10) | |
N14 | 0.7079 (3) | 0.5816 (3) | 0.2175 (3) | 0.0592 (13) | |
H14A | 0.7406 | 0.6355 | 0.2039 | 0.050* | |
H14B | 0.7447 | 0.5346 | 0.2464 | 0.050* | |
N21 | 0.7605 (3) | 0.3845 (3) | 0.3162 (2) | 0.0342 (10) | |
N22 | 0.7372 (3) | 0.4610 (3) | 0.4359 (3) | 0.0560 (13) | |
H22A | 0.6780 | 0.4516 | 0.4208 | 0.050* | |
H22B | 0.7610 | 0.4978 | 0.4839 | 0.050* | |
N23 | 0.7148 (2) | 0.2931 (3) | 0.1671 (2) | 0.0333 (10) | |
N24 | 0.6186 (3) | 0.2242 (3) | 0.0405 (2) | 0.0513 (13) | |
H24A | 0.5788 | 0.2330 | 0.0664 | 0.050* | |
H24B | 0.6009 | 0.1984 | −0.0080 | 0.050* | |
N31 | 0.6342 (4) | 0.0406 (4) | 0.4158 (3) | 0.0608 (14) | |
N41 | 0.8469 (4) | 0.0572 (5) | 0.8500 (4) | 0.0764 (17) | |
O31 | 0.5826 (2) | 0.3387 (3) | 0.34990 (19) | 0.0382 (8) | |
O32 | 0.6516 (2) | 0.2056 (2) | 0.3248 (2) | 0.0390 (9) | |
O33 | 0.5692 (3) | 0.0173 (3) | 0.3555 (3) | 0.0813 (14) | |
O34 | 0.7105 (4) | 0.0015 (3) | 0.4328 (3) | 0.0918 (15) | |
O41 | 0.8915 (4) | 0.0340 (4) | 0.8015 (4) | 0.125 (2) | |
O42 | 0.8355 (4) | 0.0051 (4) | 0.9037 (4) | 0.121 (2) | |
O43 | 0.6322 (3) | 0.0242 (3) | 0.8000 (2) | 0.0693 (12) | |
O44 | 0.6394 (2) | 0.0765 (3) | 0.9281 (2) | 0.0442 (9) | |
S11 | 0.34324 (9) | 0.22051 (12) | 0.09485 (10) | 0.0619 (5) | |
S12 | 0.54644 (11) | 0.63624 (11) | 0.10792 (10) | 0.0639 (5) | |
S21 | 0.90877 (10) | 0.45038 (12) | 0.42205 (9) | 0.0605 (5) | |
S22 | 0.80094 (10) | 0.22774 (12) | 0.06398 (9) | 0.0600 (5) | |
C11 | 0.4490 (3) | 0.3681 (4) | 0.1231 (3) | 0.0394 (13) | |
C12 | 0.3624 (3) | 0.3435 (4) | 0.0819 (3) | 0.0579 (16) | |
H12 | 0.3182 | 0.3870 | 0.0503 | 0.070* | |
C13 | 0.4568 (3) | 0.2098 (4) | 0.1580 (3) | 0.0377 (13) | |
C14 | 0.4950 (3) | 0.4635 (4) | 0.1267 (3) | 0.0400 (13) | |
C15 | 0.4637 (4) | 0.5468 (4) | 0.0854 (3) | 0.0578 (16) | |
H15 | 0.4045 | 0.5551 | 0.0490 | 0.069* | |
C16 | 0.6210 (4) | 0.5546 (4) | 0.1741 (3) | 0.0440 (14) | |
C21 | 0.8340 (3) | 0.3625 (4) | 0.2837 (3) | 0.0382 (13) | |
C22 | 0.9169 (3) | 0.3941 (4) | 0.3312 (3) | 0.0503 (15) | |
H22 | 0.9714 | 0.3864 | 0.3169 | 0.060* | |
C23 | 0.7909 (3) | 0.4301 (4) | 0.3898 (3) | 0.0389 (13) | |
C24 | 0.8087 (3) | 0.3113 (4) | 0.2028 (3) | 0.0412 (14) | |
C25 | 0.8650 (4) | 0.2812 (4) | 0.1574 (3) | 0.0518 (15) | |
H25 | 0.9288 | 0.2884 | 0.1740 | 0.062* | |
C26 | 0.7012 (3) | 0.2497 (4) | 0.0923 (3) | 0.0400 (13) | |
C31 | 0.6186 (4) | 0.1145 (5) | 0.4751 (3) | 0.0502 (15) | |
C32 | 0.6054 (3) | 0.2126 (4) | 0.4535 (3) | 0.0430 (14) | |
C33 | 0.5913 (4) | 0.2761 (5) | 0.5137 (3) | 0.0571 (16) | |
H33 | 0.5823 | 0.3428 | 0.5015 | 0.068* | |
C34 | 0.5903 (4) | 0.2412 (6) | 0.5924 (4) | 0.077 (2) | |
H34 | 0.5817 | 0.2849 | 0.6328 | 0.093* | |
C35 | 0.6019 (5) | 0.1430 (7) | 0.6115 (5) | 0.088 (3) | |
H35 | 0.5999 | 0.1202 | 0.6642 | 0.105* | |
C36 | 0.6164 (4) | 0.0787 (5) | 0.5530 (4) | 0.0694 (19) | |
H36 | 0.6246 | 0.0120 | 0.5653 | 0.083* | |
C37 | 0.6130 (3) | 0.2545 (4) | 0.3705 (3) | 0.0381 (13) | |
C41 | 0.7178 (3) | 0.1665 (4) | 0.8473 (3) | 0.0381 (12) | |
C42 | 0.8047 (4) | 0.1558 (4) | 0.8383 (3) | 0.0485 (14) | |
C43 | 0.8544 (4) | 0.2328 (5) | 0.8205 (4) | 0.073 (2) | |
H43 | 0.9123 | 0.2219 | 0.8133 | 0.087* | |
C44 | 0.8183 (6) | 0.3257 (5) | 0.8131 (4) | 0.081 (2) | |
H44 | 0.8523 | 0.3788 | 0.8027 | 0.097* | |
C45 | 0.7319 (5) | 0.3402 (5) | 0.8213 (4) | 0.0709 (19) | |
H45 | 0.7062 | 0.4029 | 0.8150 | 0.085* | |
C46 | 0.6824 (4) | 0.2605 (4) | 0.8390 (3) | 0.0541 (15) | |
H46 | 0.6242 | 0.2711 | 0.8454 | 0.065* | |
C47 | 0.6591 (3) | 0.0811 (4) | 0.8611 (3) | 0.0382 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni | 0.0287 (3) | 0.0303 (4) | 0.0332 (4) | −0.0025 (3) | 0.0066 (3) | −0.0019 (3) |
N11 | 0.030 (2) | 0.033 (3) | 0.034 (2) | −0.002 (2) | 0.0065 (18) | −0.004 (2) |
N12 | 0.050 (3) | 0.040 (3) | 0.073 (3) | −0.010 (2) | 0.010 (2) | 0.002 (3) |
N13 | 0.034 (2) | 0.032 (3) | 0.040 (2) | −0.003 (2) | 0.0092 (19) | 0.003 (2) |
N14 | 0.048 (3) | 0.039 (3) | 0.085 (4) | −0.011 (2) | 0.010 (3) | 0.009 (3) |
N21 | 0.032 (2) | 0.036 (3) | 0.032 (2) | −0.005 (2) | 0.0042 (18) | −0.005 (2) |
N22 | 0.057 (3) | 0.061 (3) | 0.046 (3) | −0.010 (3) | 0.010 (2) | −0.021 (3) |
N23 | 0.028 (2) | 0.036 (3) | 0.034 (2) | −0.0033 (19) | 0.0062 (18) | 0.001 (2) |
N24 | 0.045 (3) | 0.075 (4) | 0.033 (2) | −0.007 (3) | 0.010 (2) | −0.019 (2) |
N31 | 0.074 (4) | 0.041 (3) | 0.056 (3) | −0.008 (3) | 0.001 (3) | 0.010 (3) |
N41 | 0.051 (4) | 0.086 (5) | 0.098 (5) | −0.003 (3) | 0.031 (3) | −0.015 (4) |
O31 | 0.0360 (19) | 0.036 (2) | 0.044 (2) | 0.0023 (18) | 0.0133 (16) | −0.0016 (19) |
O32 | 0.036 (2) | 0.037 (2) | 0.044 (2) | 0.0014 (17) | 0.0126 (16) | −0.0016 (18) |
O33 | 0.097 (3) | 0.057 (3) | 0.068 (3) | −0.015 (3) | −0.010 (3) | 0.000 (3) |
O34 | 0.090 (4) | 0.068 (3) | 0.106 (4) | 0.012 (3) | 0.010 (3) | 0.002 (3) |
O41 | 0.117 (4) | 0.109 (4) | 0.188 (6) | −0.018 (4) | 0.104 (4) | −0.047 (4) |
O42 | 0.142 (5) | 0.109 (5) | 0.133 (5) | 0.071 (4) | 0.071 (4) | 0.063 (4) |
O43 | 0.100 (3) | 0.066 (3) | 0.054 (2) | −0.041 (3) | 0.041 (2) | −0.021 (2) |
O44 | 0.049 (2) | 0.051 (2) | 0.036 (2) | −0.0054 (19) | 0.0173 (17) | 0.0064 (19) |
S11 | 0.0358 (8) | 0.0717 (12) | 0.0687 (10) | −0.0177 (8) | 0.0004 (7) | −0.0052 (9) |
S12 | 0.0767 (12) | 0.0371 (9) | 0.0722 (11) | 0.0040 (8) | 0.0130 (9) | 0.0124 (9) |
S21 | 0.0438 (9) | 0.0706 (12) | 0.0553 (9) | −0.0171 (8) | −0.0041 (7) | −0.0125 (9) |
S22 | 0.0544 (10) | 0.0708 (12) | 0.0624 (10) | −0.0030 (9) | 0.0287 (8) | −0.0206 (9) |
C11 | 0.034 (3) | 0.044 (4) | 0.040 (3) | −0.001 (3) | 0.009 (2) | −0.001 (3) |
C12 | 0.035 (3) | 0.064 (4) | 0.065 (4) | −0.006 (3) | −0.001 (3) | 0.001 (4) |
C13 | 0.031 (3) | 0.044 (4) | 0.035 (3) | −0.006 (3) | 0.005 (2) | −0.006 (3) |
C14 | 0.039 (3) | 0.042 (3) | 0.037 (3) | 0.005 (3) | 0.008 (2) | 0.005 (3) |
C15 | 0.052 (4) | 0.052 (4) | 0.061 (4) | 0.011 (3) | 0.004 (3) | 0.014 (3) |
C16 | 0.053 (4) | 0.033 (3) | 0.050 (3) | −0.001 (3) | 0.022 (3) | 0.001 (3) |
C21 | 0.029 (3) | 0.044 (3) | 0.039 (3) | −0.007 (2) | 0.005 (2) | 0.003 (3) |
C22 | 0.032 (3) | 0.061 (4) | 0.058 (4) | −0.005 (3) | 0.012 (3) | −0.005 (3) |
C23 | 0.040 (3) | 0.039 (3) | 0.035 (3) | −0.006 (3) | 0.007 (2) | 0.003 (3) |
C24 | 0.032 (3) | 0.045 (4) | 0.049 (3) | −0.002 (3) | 0.015 (3) | −0.003 (3) |
C25 | 0.044 (3) | 0.052 (4) | 0.059 (4) | −0.001 (3) | 0.016 (3) | −0.004 (3) |
C26 | 0.042 (3) | 0.045 (4) | 0.033 (3) | 0.000 (3) | 0.011 (2) | 0.001 (3) |
C31 | 0.049 (4) | 0.061 (4) | 0.037 (3) | −0.011 (3) | 0.007 (3) | 0.003 (3) |
C32 | 0.042 (3) | 0.049 (4) | 0.038 (3) | −0.009 (3) | 0.012 (2) | 0.001 (3) |
C33 | 0.064 (4) | 0.068 (5) | 0.044 (4) | −0.002 (3) | 0.022 (3) | −0.004 (3) |
C34 | 0.078 (5) | 0.115 (7) | 0.048 (4) | −0.019 (5) | 0.034 (4) | −0.011 (5) |
C35 | 0.084 (5) | 0.123 (8) | 0.054 (5) | −0.029 (5) | 0.018 (4) | 0.022 (5) |
C36 | 0.071 (4) | 0.074 (5) | 0.058 (4) | −0.017 (4) | 0.010 (4) | 0.021 (4) |
C37 | 0.030 (3) | 0.040 (4) | 0.042 (3) | −0.003 (3) | 0.006 (2) | −0.002 (3) |
C41 | 0.043 (3) | 0.041 (3) | 0.031 (3) | −0.009 (3) | 0.010 (2) | −0.003 (3) |
C42 | 0.041 (3) | 0.050 (4) | 0.057 (4) | −0.012 (3) | 0.018 (3) | −0.007 (3) |
C43 | 0.063 (4) | 0.082 (5) | 0.083 (5) | −0.037 (4) | 0.037 (4) | −0.016 (5) |
C44 | 0.116 (7) | 0.057 (5) | 0.087 (5) | −0.037 (5) | 0.058 (5) | −0.003 (4) |
C45 | 0.103 (6) | 0.041 (4) | 0.069 (4) | −0.005 (4) | 0.025 (4) | 0.005 (4) |
C46 | 0.054 (4) | 0.042 (4) | 0.060 (4) | −0.001 (3) | 0.008 (3) | 0.003 (3) |
C47 | 0.035 (3) | 0.037 (3) | 0.040 (3) | −0.007 (3) | 0.008 (3) | −0.003 (3) |
Ni—N11 | 2.073 (4) | S12—C15 | 1.707 (6) |
Ni—N13 | 2.078 (4) | S12—C16 | 1.726 (5) |
Ni—N21 | 2.073 (4) | S21—C22 | 1.716 (5) |
Ni—N23 | 2.060 (4) | S21—C23 | 1.731 (5) |
Ni—O31 | 2.143 (3) | S22—C25 | 1.723 (5) |
Ni—O32 | 2.217 (3) | S22—C26 | 1.732 (5) |
Ni—C37 | 2.500 (5) | C11—C12 | 1.332 (6) |
N11—C13 | 1.314 (6) | C11—C14 | 1.466 (7) |
N11—C11 | 1.388 (6) | C12—H12 | 0.9300 |
N12—C13 | 1.320 (6) | C14—C15 | 1.335 (6) |
N12—H12A | 0.7678 | C15—H15 | 0.9300 |
N12—H12B | 0.8257 | C21—C22 | 1.342 (6) |
N13—C16 | 1.307 (6) | C21—C24 | 1.453 (7) |
N13—C14 | 1.396 (5) | C22—H22 | 0.9300 |
N14—C16 | 1.353 (6) | C24—C25 | 1.351 (6) |
N14—H14A | 0.9484 | C25—H25 | 0.9300 |
N14—H14B | 0.8884 | C31—C32 | 1.379 (7) |
N21—C23 | 1.320 (6) | C31—C36 | 1.381 (7) |
N21—C21 | 1.399 (6) | C32—C33 | 1.378 (7) |
N22—C23 | 1.332 (6) | C32—C37 | 1.516 (7) |
N22—H22A | 0.8674 | C33—C34 | 1.384 (7) |
N22—H22B | 0.9161 | C33—H33 | 0.9300 |
N23—C26 | 1.327 (5) | C34—C35 | 1.371 (9) |
N23—C24 | 1.395 (5) | C34—H34 | 0.9300 |
N24—C26 | 1.339 (6) | C35—C36 | 1.365 (9) |
N24—H24A | 0.8425 | C35—H35 | 0.9300 |
N24—H24B | 0.8409 | C36—H36 | 0.9300 |
N31—O33 | 1.220 (5) | C41—C42 | 1.375 (7) |
N31—O34 | 1.229 (6) | C41—C46 | 1.377 (7) |
N31—C31 | 1.468 (7) | C41—C47 | 1.518 (7) |
N41—O42 | 1.185 (6) | C42—C43 | 1.370 (7) |
N41—O41 | 1.228 (6) | C43—C44 | 1.367 (9) |
N41—C42 | 1.472 (8) | C43—H43 | 0.9300 |
O31—C37 | 1.243 (5) | C44—C45 | 1.369 (8) |
O32—C37 | 1.267 (5) | C44—H44 | 0.9300 |
O43—C47 | 1.240 (5) | C45—C46 | 1.396 (7) |
O44—C47 | 1.225 (5) | C45—H45 | 0.9300 |
S11—C12 | 1.720 (6) | C46—H46 | 0.9300 |
S11—C13 | 1.738 (5) | ||
N23—Ni—N21 | 80.04 (15) | C14—C15—S12 | 111.3 (4) |
N23—Ni—N11 | 101.07 (14) | C14—C15—H15 | 124.3 |
N21—Ni—N11 | 178.41 (16) | S12—C15—H15 | 124.3 |
N23—Ni—N13 | 98.01 (15) | N13—C16—N14 | 124.3 (5) |
N21—Ni—N13 | 98.64 (15) | N13—C16—S12 | 114.6 (4) |
N11—Ni—N13 | 80.09 (15) | N14—C16—S12 | 121.2 (4) |
N23—Ni—O31 | 157.03 (14) | C22—C21—N21 | 115.0 (5) |
N21—Ni—O31 | 89.64 (13) | C22—C21—C24 | 129.8 (5) |
N11—Ni—O31 | 89.73 (13) | N21—C21—C24 | 115.2 (4) |
N13—Ni—O31 | 103.83 (14) | C21—C22—S21 | 111.0 (4) |
N23—Ni—O32 | 98.57 (14) | C21—C22—H22 | 124.5 |
N21—Ni—O32 | 87.37 (13) | S21—C22—H22 | 124.5 |
N11—Ni—O32 | 93.59 (14) | N21—C23—N22 | 124.3 (5) |
N13—Ni—O32 | 163.11 (14) | N21—C23—S21 | 114.2 (4) |
O31—Ni—O32 | 60.22 (12) | N22—C23—S21 | 121.4 (4) |
N23—Ni—C37 | 128.30 (17) | C25—C24—N23 | 116.4 (5) |
N21—Ni—C37 | 87.41 (15) | C25—C24—C21 | 127.7 (5) |
N11—Ni—C37 | 92.77 (15) | N23—C24—C21 | 115.9 (4) |
N13—Ni—C37 | 133.54 (17) | C24—C25—S22 | 109.8 (4) |
O31—Ni—C37 | 29.82 (13) | C24—C25—H25 | 125.1 |
O32—Ni—C37 | 30.42 (13) | S22—C25—H25 | 125.1 |
C13—N11—C11 | 110.6 (4) | N23—C26—N24 | 124.8 (4) |
C13—N11—Ni | 134.5 (3) | N23—C26—S22 | 114.5 (4) |
C11—N11—Ni | 114.3 (3) | N24—C26—S22 | 120.7 (4) |
C13—N12—H12A | 119.7 | C32—C31—C36 | 122.7 (6) |
C13—N12—H12B | 117.2 | C32—C31—N31 | 121.9 (5) |
H12A—N12—H12B | 114.3 | C36—C31—N31 | 115.4 (6) |
C16—N13—C14 | 110.2 (4) | C33—C32—C31 | 117.4 (5) |
C16—N13—Ni | 135.8 (4) | C33—C32—C37 | 118.8 (5) |
C14—N13—Ni | 113.9 (3) | C31—C32—C37 | 123.6 (5) |
C16—N14—H14A | 125.4 | C32—C33—C34 | 120.4 (6) |
C16—N14—H14B | 116.8 | C32—C33—H33 | 119.8 |
H14A—N14—H14B | 113.0 | C34—C33—H33 | 119.8 |
C23—N21—C21 | 110.3 (4) | C35—C34—C33 | 120.9 (7) |
C23—N21—Ni | 135.4 (3) | C35—C34—H34 | 119.5 |
C21—N21—Ni | 114.3 (3) | C33—C34—H34 | 119.5 |
C23—N22—H22A | 122.8 | C36—C35—C34 | 119.7 (7) |
C23—N22—H22B | 120.8 | C36—C35—H35 | 120.1 |
H22A—N22—H22B | 116.3 | C34—C35—H35 | 120.1 |
C26—N23—C24 | 109.5 (4) | C35—C36—C31 | 118.9 (7) |
C26—N23—Ni | 136.0 (3) | C35—C36—H36 | 120.6 |
C24—N23—Ni | 114.5 (3) | C31—C36—H36 | 120.6 |
C26—N24—H24A | 108.4 | O31—C37—O32 | 121.3 (5) |
C26—N24—H24B | 133.9 | O31—C37—C32 | 118.2 (5) |
H24A—N24—H24B | 117.5 | O32—C37—C32 | 120.5 (5) |
O33—N31—O34 | 123.9 (6) | O31—C37—Ni | 59.0 (3) |
O33—N31—C31 | 118.1 (5) | O32—C37—Ni | 62.3 (2) |
O34—N31—C31 | 117.8 (5) | C32—C37—Ni | 174.9 (4) |
O42—N41—O41 | 124.0 (7) | C42—C41—C46 | 116.4 (5) |
O42—N41—C42 | 119.3 (6) | C42—C41—C47 | 123.8 (5) |
O41—N41—C42 | 116.7 (7) | C46—C41—C47 | 119.7 (5) |
C37—O31—Ni | 91.2 (3) | C43—C42—C41 | 123.1 (6) |
C37—O32—Ni | 87.2 (3) | C43—C42—N41 | 118.6 (6) |
C12—S11—C13 | 89.0 (3) | C41—C42—N41 | 118.4 (5) |
C15—S12—C16 | 89.1 (3) | C44—C43—C42 | 119.6 (6) |
C22—S21—C23 | 89.4 (2) | C44—C43—H43 | 120.2 |
C25—S22—C26 | 89.8 (3) | C42—C43—H43 | 120.2 |
C12—C11—N11 | 115.5 (5) | C43—C44—C45 | 119.5 (6) |
C12—C11—C14 | 129.0 (5) | C43—C44—H44 | 120.2 |
N11—C11—C14 | 115.5 (4) | C45—C44—H44 | 120.2 |
C11—C12—S11 | 110.9 (4) | C44—C45—C46 | 119.8 (6) |
C11—C12—H12 | 124.5 | C44—C45—H45 | 120.1 |
S11—C12—H12 | 124.5 | C46—C45—H45 | 120.1 |
N11—C13—N12 | 124.8 (4) | C41—C46—C45 | 121.6 (6) |
N11—C13—S11 | 113.9 (4) | C41—C46—H46 | 119.2 |
N12—C13—S11 | 121.3 (4) | C45—C46—H46 | 119.2 |
C15—C14—N13 | 114.8 (5) | O44—C47—O43 | 126.1 (5) |
C15—C14—C11 | 129.5 (5) | O44—C47—C41 | 118.7 (5) |
N13—C14—C11 | 115.7 (4) | O43—C47—C41 | 115.1 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···O43i | 0.77 | 2.01 | 2.779 (6) | 176 |
N12—H12B···O32 | 0.83 | 2.23 | 2.982 (6) | 151 |
N12—H12B···O33 | 0.83 | 2.48 | 2.999 (6) | 122 |
N14—H14A···O32ii | 0.95 | 2.06 | 2.953 (5) | 156 |
N14—H14B···N21 | 0.89 | 2.32 | 3.114 (6) | 149 |
N22—H22A···O31 | 0.87 | 2.20 | 2.886 (6) | 136 |
N22—H22B···O44iii | 0.92 | 2.06 | 2.923 (6) | 156 |
N24—H24A···N11 | 0.84 | 2.39 | 3.204 (5) | 161 |
N24—H24B···O44iv | 0.84 | 2.13 | 2.810 (5) | 137 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C7H4NO4)(C6H6N4S2)2](C7H4NO4) |
Mr | 787.47 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 295 |
a, b, c (Å) | 15.1514 (18), 13.5905 (16), 16.4702 (19) |
β (°) | 106.901 (2) |
V (Å3) | 3245.0 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.92 |
Crystal size (mm) | 0.20 × 0.17 × 0.14 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID IP |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.812, 0.880 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16530, 5721, 3217 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.123, 1.00 |
No. of reflections | 5721 |
No. of parameters | 443 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.37 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), PROCESS-AUTO, CrystalStructure (Rigaku/MSC & Rigaku, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
Ni—N11 | 2.073 (4) | Ni—N23 | 2.060 (4) |
Ni—N13 | 2.078 (4) | Ni—O31 | 2.143 (3) |
Ni—N21 | 2.073 (4) | Ni—O32 | 2.217 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12A···O43i | 0.77 | 2.01 | 2.779 (6) | 176 |
N12—H12B···O32 | 0.83 | 2.23 | 2.982 (6) | 151 |
N12—H12B···O33 | 0.83 | 2.48 | 2.999 (6) | 122 |
N14—H14A···O32ii | 0.95 | 2.06 | 2.953 (5) | 156 |
N14—H14B···N21 | 0.89 | 2.32 | 3.114 (6) | 149 |
N22—H22A···O31 | 0.87 | 2.20 | 2.886 (6) | 136 |
N22—H22B···O44iii | 0.92 | 2.06 | 2.923 (6) | 156 |
N24—H24A···N11 | 0.84 | 2.39 | 3.204 (5) | 161 |
N24—H24B···O44iv | 0.84 | 2.13 | 2.810 (5) | 137 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+3/2, y+1/2, −z+1/2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y, z−1. |
Transition metal complexes of 2,2'-diamino-4,4'-bi-1,3-thiazole (DABT) have shown potential application in the field of soft magnetic material (Liu et al., 2001). As part of serial structural investigation of metal complexes with DABT (Liu & Xu, 2004), the title NiII complex was recently prepared and its X-ray structure is presented here.
The molecular structure of the title compound is shown in Fig. 1. The Ni ion has a distorted octahedral coordinatation geometry formed by one 2-nitrobenzoate anion and two DABT ligands. Within the complex, two DABT moieties are approximately perpendicular to each other with a dihedral angle of 81.23 (7)°. This is comparable to 84.3 (4)° found in a NiII complex of DABT reported previously (Liu & Xu, 2003). Each DABT moiety is approximately coplanar coordinated to Ni atom, the dihedral angles between two thiazole rings being 6.2 (3) and 2.6 (2)°, respectively, which agree with 4.57 (7)° found in [Mn(DABT)(oxydiacetate)] (Luo et al., 2004). The average Ni—N bond distance (Table 1) is shorter than the value of 2.113 (2) Å of average Ni—N bond distance found in reported NiII complex of DABT (Liu & Xu, 2003).
The extensive hydrogen bonding occurs in the crystal structure (Table 2). While 2-nitrobenzoate anion links with complex cation via N—H···O hydrogen bonding, the N—H···O hydrogen bonding is also observed between complex cations. They help to stabilize the crystal structure.