Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043334/at2387sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043334/at2387Isup2.hkl |
CCDC reference: 663719
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean (C-C) = 0.002 Å
- Disorder in main residue
- R factor = 0.057
- wR factor = 0.147
- Data-to-parameter ratio = 12.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 27.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.18 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 17.10 Deg. C10' -N2 -C10 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 16.10 Deg. C7' -C6 -C7 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H6A -C6 -H6C 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. H6B -C6 -H6D 1.555 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 111
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
1,3-Dibutyl-1H-purine-2,6(3H,7H)-dione (1 g) was added to an anhydrous N,N-dimethylformamide (50 ml), with stirring at 350 K. The resulting colourless solution was filtered and filtrate was allowed to stand in air at room temperature for one month, yielding colourless crystals of (I).
The two butyl (C6—C9) and (C10—C13) groups are disordered in two positions with the site-occupancy ratios of 0.564 (1)/0.436 (1) and 0.644 (1)/0.356 (1), respectively. In the disordered group, the C(methyl)-C(methyl) and C(methyl)-N(pyrimidine) distances were restrained to 1.54 (1) and 1.48 (1) Å, and the C and N atoms of the minor component were refined isotropically. The N-bound H atom was located in a difference Fourier map and refined freely. C-bound H atoms were included in calculated positions, with C—H = 0.93 (aromatic) or 0.96 Å (methyl), and refined using a riding model, with Uiso(H) = 1.2Ueq(C) for aromatic H or 1.5Ueq(C) for methyl H atoms.
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In the crystal structurer, the molecules are linked via weak intermolecular N–H···N hydrogen bonds (Table 1), to form a supramolecular arrangement, as illustrated in Fig.2.
For general background, see: Belloni et al. (2005); Kahwa et al. (1986); Parashar et al. (1988); Santos et al. (2001); Tynan et al. (2005).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005).
C13H20N4O2 | F(000) = 568 |
Mr = 264.33 | Dx = 1.246 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: -P 2ybc | Cell parameters from 2683 reflections |
a = 14.2300 (14) Å | θ = 2.6–27.9° |
b = 9.4120 (8) Å | µ = 0.09 mm−1 |
c = 10.728 (1) Å | T = 113 K |
β = 101.290 (4)° | Block, colourless |
V = 1409.0 (2) Å3 | 0.32 × 0.30 × 0.16 mm |
Z = 4 |
Rigaku Saturn diffractometer | 3070 independent reflections |
Radiation source: rotating anode | 2515 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.042 |
Detector resolution: 7.31 pixels mm-1 | θmax = 27.0°, θmin = 2.6° |
ω scans | h = −18→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −12→11 |
Tmin = 0.973, Tmax = 0.986 | l = −13→13 |
12057 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0761P)2 + 0.1029P] where P = (Fo2 + 2Fc2)/3 |
3070 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.21 e Å−3 |
111 restraints | Δρmin = −0.23 e Å−3 |
C13H20N4O2 | V = 1409.0 (2) Å3 |
Mr = 264.33 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.2300 (14) Å | µ = 0.09 mm−1 |
b = 9.4120 (8) Å | T = 113 K |
c = 10.728 (1) Å | 0.32 × 0.30 × 0.16 mm |
β = 101.290 (4)° |
Rigaku Saturn diffractometer | 3070 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2515 reflections with I > 2σ(I) |
Tmin = 0.973, Tmax = 0.986 | Rint = 0.042 |
12057 measured reflections |
R[F2 > 2σ(F2)] = 0.057 | 111 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.21 e Å−3 |
3070 reflections | Δρmin = −0.23 e Å−3 |
245 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 | Occ. (<1) | |
O1 | 0.38973 (8) | 0.87003 (12) | 0.49767 (10) | 0.0374 (3) | |
O2 | 0.25608 (11) | 0.47462 (15) | 0.28230 (11) | 0.0601 (4) | |
N1 | 0.32215 (9) | 0.67085 (15) | 0.39159 (12) | 0.0360 (4) | |
N2 | 0.35377 (10) | 0.43656 (14) | 0.47432 (12) | 0.0367 (4) | |
N3 | 0.48557 (9) | 0.66280 (14) | 0.70573 (12) | 0.0293 (3) | |
N4 | 0.45896 (10) | 0.42872 (13) | 0.68474 (12) | 0.0349 (3) | |
C1 | 0.38066 (11) | 0.74015 (17) | 0.49472 (13) | 0.0308 (4) | |
C2 | 0.30763 (13) | 0.52338 (19) | 0.37712 (15) | 0.0416 (4) | |
C3 | 0.41034 (11) | 0.49831 (17) | 0.57962 (14) | 0.0311 (4) | |
C4 | 0.42479 (11) | 0.64183 (16) | 0.58947 (14) | 0.0289 (4) | |
C5 | 0.50294 (11) | 0.53407 (16) | 0.75810 (15) | 0.0332 (4) | |
H5A | 0.5425 | 0.5188 | 0.8392 | 0.040* | |
C6 | 0.27299 (11) | 0.76074 (19) | 0.28581 (15) | 0.0395 (4) | |
H6A | 0.2623 | 0.7051 | 0.2093 | 0.047* | 0.56 (2) |
H6B | 0.3143 | 0.8383 | 0.2745 | 0.047* | 0.56 (2) |
H6C | 0.2623 | 0.7051 | 0.2093 | 0.047* | 0.44 (2) |
H6D | 0.3143 | 0.8383 | 0.2745 | 0.047* | 0.44 (2) |
C7 | 0.1760 (4) | 0.8211 (10) | 0.3046 (8) | 0.0415 (16) | 0.56 (2) |
H7A | 0.1304 | 0.7419 | 0.3057 | 0.050* | 0.56 (2) |
H7B | 0.1848 | 0.8701 | 0.3878 | 0.050* | 0.56 (2) |
C8 | 0.1341 (4) | 0.9254 (11) | 0.1991 (8) | 0.0501 (18) | 0.56 (2) |
H8A | 0.1291 | 0.8768 | 0.1162 | 0.060* | 0.56 (2) |
H8B | 0.1794 | 1.0056 | 0.2008 | 0.060* | 0.56 (2) |
C9 | 0.0357 (4) | 0.9851 (14) | 0.2079 (7) | 0.061 (2) | 0.56 (2) |
H9A | 0.0139 | 1.0497 | 0.1364 | 0.091* | 0.56 (2) |
H9B | 0.0402 | 1.0371 | 0.2880 | 0.091* | 0.56 (2) |
H9C | −0.0102 | 0.9069 | 0.2048 | 0.091* | 0.56 (2) |
C10 | 0.3504 (3) | 0.2772 (4) | 0.4671 (7) | 0.0349 (11) | 0.645 (3) |
H10A | 0.4141 | 0.2381 | 0.5049 | 0.042* | 0.645 (3) |
H10B | 0.3345 | 0.2474 | 0.3769 | 0.042* | 0.645 (3) |
C11 | 0.2754 (2) | 0.2176 (3) | 0.5377 (3) | 0.0381 (7) | 0.645 (3) |
H11A | 0.2796 | 0.1126 | 0.5384 | 0.046* | 0.645 (3) |
H11B | 0.2905 | 0.2506 | 0.6270 | 0.046* | 0.645 (3) |
C12 | 0.1739 (2) | 0.2610 (3) | 0.4795 (3) | 0.0429 (8) | 0.645 (3) |
H12A | 0.1583 | 0.2274 | 0.3904 | 0.051* | 0.645 (3) |
H12B | 0.1695 | 0.3659 | 0.4785 | 0.051* | 0.645 (3) |
C13 | 0.1011 (2) | 0.2008 (5) | 0.5521 (3) | 0.0639 (11) | 0.645 (3) |
H13A | 0.0365 | 0.2312 | 0.5110 | 0.096* | 0.645 (3) |
H13B | 0.1153 | 0.2355 | 0.6398 | 0.096* | 0.645 (3) |
H13C | 0.1044 | 0.0968 | 0.5520 | 0.096* | 0.645 (3) |
C7' | 0.1682 (4) | 0.7800 (13) | 0.2886 (10) | 0.038 (2) | 0.44 (2) |
H7'A | 0.1609 | 0.8244 | 0.3699 | 0.045* | 0.44 (2) |
H7'B | 0.1356 | 0.6866 | 0.2814 | 0.045* | 0.44 (2) |
C8' | 0.1235 (5) | 0.8757 (13) | 0.1765 (9) | 0.045 (2) | 0.44 (2) |
H8'A | 0.1634 | 0.9619 | 0.1761 | 0.054* | 0.44 (2) |
H8'B | 0.1222 | 0.8243 | 0.0956 | 0.054* | 0.44 (2) |
C9' | 0.0225 (5) | 0.9189 (16) | 0.1858 (9) | 0.056 (2) | 0.44 (2) |
H9'A | −0.0062 | 0.9736 | 0.1103 | 0.085* | 0.44 (2) |
H9'B | 0.0244 | 0.9773 | 0.2619 | 0.085* | 0.44 (2) |
H9'C | −0.0160 | 0.8336 | 0.1914 | 0.085* | 0.44 (2) |
C10' | 0.3200 (5) | 0.2900 (8) | 0.4624 (12) | 0.032 (2) | 0.355 (3) |
H10C | 0.3723 | 0.2276 | 0.5057 | 0.039* | 0.355 (3) |
H10D | 0.3066 | 0.2642 | 0.3712 | 0.039* | 0.355 (3) |
C11' | 0.2311 (4) | 0.2593 (5) | 0.5160 (5) | 0.0303 (12) | 0.355 (3) |
H11C | 0.1808 | 0.3296 | 0.4822 | 0.036* | 0.355 (3) |
H11D | 0.2465 | 0.2692 | 0.6096 | 0.036* | 0.355 (3) |
C12' | 0.1934 (3) | 0.1097 (5) | 0.4812 (4) | 0.0349 (12) | 0.355 (3) |
H12C | 0.1786 | 0.1000 | 0.3875 | 0.042* | 0.355 (3) |
H12D | 0.2439 | 0.0398 | 0.5151 | 0.042* | 0.355 (3) |
C13' | 0.1040 (3) | 0.0768 (6) | 0.5334 (5) | 0.0423 (14) | 0.355 (3) |
H13D | 0.0857 | −0.0226 | 0.5156 | 0.063* | 0.355 (3) |
H13E | 0.0516 | 0.1390 | 0.4928 | 0.063* | 0.355 (3) |
H13F | 0.1170 | 0.0928 | 0.6254 | 0.063* | 0.355 (3) |
H3 | 0.5081 (14) | 0.755 (2) | 0.7458 (18) | 0.052 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0494 (7) | 0.0245 (7) | 0.0324 (6) | −0.0049 (5) | −0.0065 (5) | 0.0055 (5) |
O2 | 0.0935 (10) | 0.0496 (9) | 0.0263 (7) | −0.0352 (7) | −0.0149 (6) | 0.0034 (6) |
N1 | 0.0468 (8) | 0.0326 (8) | 0.0238 (7) | −0.0123 (6) | −0.0046 (6) | 0.0061 (6) |
N2 | 0.0573 (9) | 0.0245 (8) | 0.0243 (7) | −0.0140 (6) | −0.0021 (6) | −0.0006 (5) |
N3 | 0.0398 (7) | 0.0183 (7) | 0.0254 (7) | −0.0001 (5) | −0.0046 (5) | 0.0004 (5) |
N4 | 0.0506 (8) | 0.0204 (7) | 0.0292 (7) | −0.0015 (6) | −0.0029 (6) | 0.0000 (5) |
C1 | 0.0381 (8) | 0.0260 (9) | 0.0255 (8) | −0.0064 (6) | −0.0005 (6) | 0.0031 (6) |
C2 | 0.0604 (11) | 0.0355 (10) | 0.0248 (8) | −0.0206 (8) | −0.0017 (7) | 0.0015 (7) |
C3 | 0.0436 (8) | 0.0241 (8) | 0.0232 (8) | −0.0053 (6) | 0.0006 (6) | −0.0009 (6) |
C4 | 0.0376 (8) | 0.0235 (8) | 0.0229 (8) | −0.0040 (6) | −0.0007 (6) | −0.0002 (6) |
C5 | 0.0454 (9) | 0.0214 (8) | 0.0282 (8) | 0.0028 (6) | −0.0038 (6) | 0.0008 (6) |
C6 | 0.0436 (9) | 0.0445 (11) | 0.0259 (8) | −0.0127 (7) | −0.0041 (7) | 0.0134 (7) |
C7 | 0.038 (2) | 0.049 (3) | 0.032 (3) | −0.027 (2) | −0.0045 (16) | 0.010 (2) |
C8 | 0.039 (2) | 0.069 (4) | 0.037 (3) | −0.005 (2) | −0.0061 (17) | 0.022 (3) |
C9 | 0.045 (2) | 0.085 (5) | 0.046 (3) | −0.001 (3) | −0.0051 (18) | 0.013 (3) |
C10 | 0.052 (3) | 0.0205 (17) | 0.0289 (17) | −0.0143 (17) | 0.000 (2) | −0.0012 (13) |
C11 | 0.0515 (19) | 0.0304 (17) | 0.0293 (15) | −0.0069 (13) | 0.0006 (14) | 0.0045 (12) |
C12 | 0.0546 (19) | 0.0445 (18) | 0.0288 (15) | −0.0035 (15) | 0.0063 (14) | 0.0047 (12) |
C13 | 0.064 (2) | 0.076 (3) | 0.054 (2) | −0.0054 (18) | 0.0149 (16) | 0.0183 (18) |
C7' | 0.036 (3) | 0.049 (4) | 0.023 (3) | −0.025 (3) | −0.0071 (18) | 0.009 (3) |
C8' | 0.036 (3) | 0.062 (5) | 0.033 (3) | −0.012 (3) | −0.002 (2) | 0.010 (3) |
C9' | 0.046 (3) | 0.078 (6) | 0.041 (3) | −0.005 (3) | −0.001 (2) | 0.000 (4) |
C10' | 0.034 (4) | 0.034 (3) | 0.028 (3) | −0.006 (3) | 0.003 (3) | −0.008 (2) |
C11' | 0.038 (3) | 0.028 (3) | 0.022 (3) | −0.001 (2) | −0.001 (2) | −0.001 (2) |
C12' | 0.041 (2) | 0.030 (3) | 0.031 (2) | −0.0093 (18) | 0.0019 (18) | −0.0001 (19) |
C13' | 0.041 (2) | 0.046 (3) | 0.039 (3) | −0.016 (2) | 0.006 (2) | 0.007 (2) |
O1—C1 | 1.2290 (18) | C10—H10A | 0.9900 |
O2—C2 | 1.2212 (18) | C10—H10B | 0.9900 |
N1—C2 | 1.407 (2) | C11—C12 | 1.513 (4) |
N1—C1 | 1.4079 (18) | C11—H11A | 0.9900 |
N1—C6 | 1.4772 (19) | C11—H11B | 0.9900 |
N2—C3 | 1.3805 (19) | C12—C13 | 1.523 (4) |
N2—C2 | 1.385 (2) | C12—H12A | 0.9900 |
N2—C10' | 1.458 (7) | C12—H12B | 0.9900 |
N2—C10 | 1.502 (4) | C13—H13A | 0.9800 |
N3—C5 | 1.338 (2) | C13—H13B | 0.9800 |
N3—C4 | 1.3858 (19) | C13—H13C | 0.9800 |
N3—H3 | 0.99 (2) | C7'—C8' | 1.538 (7) |
N4—C5 | 1.3422 (19) | C7'—H7'A | 0.9900 |
N4—C3 | 1.3689 (19) | C7'—H7'B | 0.9900 |
C1—C4 | 1.426 (2) | C8'—C9' | 1.516 (7) |
C3—C4 | 1.367 (2) | C8'—H8'A | 0.9900 |
C5—H5A | 0.9500 | C8'—H8'B | 0.9900 |
C6—C7' | 1.508 (6) | C9'—H9'A | 0.9800 |
C6—C7 | 1.542 (6) | C9'—H9'B | 0.9800 |
C6—H6A | 0.9600 | C9'—H9'C | 0.9800 |
C6—H6B | 0.9599 | C10'—C11' | 1.516 (7) |
C6—H6C | 0.9600 | C10'—H10C | 0.9900 |
C6—H6D | 0.9599 | C10'—H10D | 0.9900 |
C7—C8 | 1.528 (6) | C11'—C12' | 1.527 (5) |
C7—H7A | 0.9900 | C11'—H11C | 0.9900 |
C7—H7B | 0.9900 | C11'—H11D | 0.9900 |
C8—C9 | 1.530 (6) | C12'—C13' | 1.519 (5) |
C8—H8A | 0.9900 | C12'—H12C | 0.9900 |
C8—H8B | 0.9900 | C12'—H12D | 0.9900 |
C9—H9A | 0.9800 | C13'—H13D | 0.9800 |
C9—H9B | 0.9800 | C13'—H13E | 0.9800 |
C9—H9C | 0.9800 | C13'—H13F | 0.9800 |
C10—C11 | 1.531 (5) | ||
C2—N1—C1 | 126.51 (13) | N2—C10—C11 | 111.0 (4) |
C2—N1—C6 | 116.29 (13) | N2—C10—H10A | 109.4 |
C1—N1—C6 | 117.17 (13) | C11—C10—H10A | 109.4 |
C3—N2—C2 | 118.84 (14) | N2—C10—H10B | 109.4 |
C3—N2—C10' | 126.8 (5) | C11—C10—H10B | 109.4 |
C2—N2—C10' | 113.1 (5) | H10A—C10—H10B | 108.0 |
C3—N2—C10 | 118.1 (3) | C12—C11—C10 | 113.5 (3) |
C2—N2—C10 | 123.0 (3) | C12—C11—H11A | 108.9 |
C10'—N2—C10 | 17.1 (4) | C10—C11—H11A | 108.9 |
C5—N3—C4 | 106.28 (13) | C12—C11—H11B | 108.9 |
C5—N3—H3 | 126.3 (11) | C10—C11—H11B | 108.9 |
C4—N3—H3 | 127.3 (11) | H11A—C11—H11B | 107.7 |
C5—N4—C3 | 103.42 (12) | C11—C12—C13 | 112.3 (3) |
O1—C1—N1 | 121.60 (13) | C11—C12—H12A | 109.1 |
O1—C1—C4 | 126.71 (14) | C13—C12—H12A | 109.1 |
N1—C1—C4 | 111.69 (13) | C11—C12—H12B | 109.1 |
O2—C2—N2 | 121.63 (16) | C13—C12—H12B | 109.1 |
O2—C2—N1 | 120.91 (16) | H12A—C12—H12B | 107.9 |
N2—C2—N1 | 117.46 (13) | C6—C7'—C8' | 108.3 (6) |
C4—C3—N4 | 111.40 (13) | C6—C7'—H7'A | 110.0 |
C4—C3—N2 | 122.27 (14) | C8'—C7'—H7'A | 110.0 |
N4—C3—N2 | 126.33 (15) | C6—C7'—H7'B | 110.0 |
C3—C4—N3 | 105.56 (13) | C8'—C7'—H7'B | 110.0 |
C3—C4—C1 | 123.19 (13) | H7'A—C7'—H7'B | 108.4 |
N3—C4—C1 | 131.24 (14) | C9'—C8'—C7' | 110.9 (6) |
N3—C5—N4 | 113.34 (13) | C9'—C8'—H8'A | 109.5 |
N3—C5—H5A | 123.3 | C7'—C8'—H8'A | 109.5 |
N4—C5—H5A | 123.3 | C9'—C8'—H8'B | 109.5 |
N1—C6—C7' | 112.0 (3) | C7'—C8'—H8'B | 109.5 |
N1—C6—C7 | 114.3 (3) | H8'A—C8'—H8'B | 108.0 |
C7'—C6—C7 | 16.1 (4) | C8'—C9'—H9'A | 109.5 |
N1—C6—H6A | 108.4 | C8'—C9'—H9'B | 109.5 |
C7'—C6—H6A | 95.2 | H9'A—C9'—H9'B | 109.5 |
C7—C6—H6A | 108.5 | C8'—C9'—H9'C | 109.5 |
N1—C6—H6B | 108.8 | H9'A—C9'—H9'C | 109.5 |
C7'—C6—H6B | 123.0 | H9'B—C9'—H9'C | 109.5 |
C7—C6—H6B | 108.9 | N2—C10'—C11' | 115.6 (6) |
H6A—C6—H6B | 107.7 | N2—C10'—H10C | 108.4 |
N1—C6—H6C | 108.4 | C11'—C10'—H10C | 108.4 |
C7'—C6—H6C | 95.2 | N2—C10'—H10D | 108.4 |
C7—C6—H6C | 108.5 | C11'—C10'—H10D | 108.4 |
H6A—C6—H6C | 0.0 | H10C—C10'—H10D | 107.4 |
H6B—C6—H6C | 107.7 | C10'—C11'—C12' | 111.3 (5) |
N1—C6—H6D | 108.8 | C10'—C11'—H11C | 109.4 |
C7'—C6—H6D | 123.0 | C12'—C11'—H11C | 109.4 |
C7—C6—H6D | 108.9 | C10'—C11'—H11D | 109.4 |
H6A—C6—H6D | 107.7 | C12'—C11'—H11D | 109.4 |
H6B—C6—H6D | 0.0 | H11C—C11'—H11D | 108.0 |
H6C—C6—H6D | 107.7 | C13'—C12'—C11' | 112.2 (4) |
C8—C7—C6 | 111.6 (5) | C13'—C12'—H12C | 109.2 |
C8—C7—H7A | 109.3 | C11'—C12'—H12C | 109.2 |
C6—C7—H7A | 109.3 | C13'—C12'—H12D | 109.2 |
C8—C7—H7B | 109.3 | C11'—C12'—H12D | 109.2 |
C6—C7—H7B | 109.3 | H12C—C12'—H12D | 107.9 |
H7A—C7—H7B | 108.0 | C12'—C13'—H13D | 109.5 |
C7—C8—C9 | 114.8 (5) | C12'—C13'—H13E | 109.5 |
C7—C8—H8A | 108.6 | H13D—C13'—H13E | 109.5 |
C9—C8—H8A | 108.6 | C12'—C13'—H13F | 109.5 |
C7—C8—H8B | 108.6 | H13D—C13'—H13F | 109.5 |
C9—C8—H8B | 108.6 | H13E—C13'—H13F | 109.5 |
H8A—C8—H8B | 107.5 | ||
C2—N1—C1—O1 | 178.94 (15) | C5—N3—C4—C1 | 177.99 (16) |
C6—N1—C1—O1 | 0.8 (2) | O1—C1—C4—C3 | 179.40 (16) |
C2—N1—C1—C4 | −1.2 (2) | N1—C1—C4—C3 | −0.5 (2) |
C6—N1—C1—C4 | −179.29 (13) | O1—C1—C4—N3 | 1.1 (3) |
C3—N2—C2—O2 | −179.37 (16) | N1—C1—C4—N3 | −178.77 (15) |
C10'—N2—C2—O2 | −11.1 (4) | C4—N3—C5—N4 | 0.62 (18) |
C10—N2—C2—O2 | 4.7 (3) | C3—N4—C5—N3 | −0.42 (18) |
C3—N2—C2—N1 | 0.5 (2) | C2—N1—C6—C7' | 78.2 (6) |
C10'—N2—C2—N1 | 168.7 (4) | C1—N1—C6—C7' | −103.5 (6) |
C10—N2—C2—N1 | −175.4 (3) | C2—N1—C6—C7 | 95.6 (4) |
C1—N1—C2—O2 | −178.94 (16) | C1—N1—C6—C7 | −86.1 (4) |
C6—N1—C2—O2 | −0.8 (2) | N1—C6—C7—C8 | 173.9 (4) |
C1—N1—C2—N2 | 1.2 (2) | C7'—C6—C7—C8 | −101 (2) |
C6—N1—C2—N2 | 179.30 (14) | C6—C7—C8—C9 | 177.5 (5) |
C5—N4—C3—C4 | 0.05 (18) | C3—N2—C10—C11 | 85.2 (4) |
C5—N4—C3—N2 | 179.53 (15) | C2—N2—C10—C11 | −98.8 (4) |
C2—N2—C3—C4 | −2.1 (2) | C10'—N2—C10—C11 | −40 (2) |
C10'—N2—C3—C4 | −168.5 (4) | N2—C10—C11—C12 | 64.2 (5) |
C10—N2—C3—C4 | 174.0 (3) | C10—C11—C12—C13 | −179.7 (3) |
C2—N2—C3—N4 | 178.47 (15) | N1—C6—C7'—C8' | 179.4 (4) |
C10'—N2—C3—N4 | 12.0 (5) | C7—C6—C7'—C8' | 77.8 (19) |
C10—N2—C3—N4 | −5.4 (3) | C6—C7'—C8'—C9' | −170.8 (6) |
N4—C3—C4—N3 | 0.31 (18) | C3—N2—C10'—C11' | 82.6 (8) |
N2—C3—C4—N3 | −179.20 (14) | C2—N2—C10'—C11' | −84.5 (9) |
N4—C3—C4—C1 | −178.37 (14) | C10—N2—C10'—C11' | 147 (3) |
N2—C3—C4—C1 | 2.1 (2) | N2—C10'—C11'—C12' | 171.5 (7) |
C5—N3—C4—C3 | −0.54 (17) | C10'—C11'—C12'—C13' | −179.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N4i | 0.99 (2) | 1.82 (2) | 2.8115 (19) | 176.0 (18) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C13H20N4O2 |
Mr | 264.33 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 14.2300 (14), 9.4120 (8), 10.728 (1) |
β (°) | 101.290 (4) |
V (Å3) | 1409.0 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.30 × 0.16 |
Data collection | |
Diffractometer | Rigaku Saturn |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.973, 0.986 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12057, 3070, 2515 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.147, 1.11 |
No. of reflections | 3070 |
No. of parameters | 245 |
No. of restraints | 111 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.23 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), CrystalStructure (Rigaku/MSC, 2005).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N4i | 0.99 (2) | 1.82 (2) | 2.8115 (19) | 176.0 (18) |
Symmetry code: (i) −x+1, y+1/2, −z+3/2. |
In order to establish control over the preparation of crystalline solid materials so that their architecture and properties are predictable (Belloni et al., 2005; Tynan et al., 2005; Parashar et al., 1988), the synthesis of new and designed crystal structures has become a major strand of modern chemistry. Metal complexes based on Schiff bases have attracted much attention because they can be utilized as model compounds of the active centres in various proteins and enzymes (Kahwa et al., 1986; Santos et al., 2001). As part of an investigation of the coordination properties of Shiff bases functioning as ligands, we report the synthesis and crystal structure of the title compound, (I).
In the molecular structure of the compound (I) (Fig. 1), the geometric parameters are normal. In the crystal structurer, the molecules are linked via weak intermolecular N–H···N hydrogen bonds (Table 1), to form a supramolecular arrangement, as illustrated in Fig.2.