Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807032667/wk2069sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807032667/wk2069Isup2.hkl |
CCDC reference: 657727
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.042
- wR factor = 0.112
- Data-to-parameter ratio = 8.8
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_2_C Chirality of atom sites is inverted? From the CIF: _refine_ls_abs_structure_Flack 10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT147_ALERT_1_C su on Symmetry Constrained Cell Angle(s) ....... ? PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 500 Ang.
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 28.31 From the CIF: _reflns_number_total 1670 Count of symmetry unique reflns 1695 Completeness (_total/calc) 98.53% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 4 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Peng et al. (2006); Pleier et al. (2001); Zheng et al. (2003).
All reagents were purchased (Aldrich) and used without further purification. The title compound was synthesized according to the literature method (Pleier et al., 2001). The title compound (0.552 g, 0.002 mol) was dissolved into 20 ml DMF. After heating at 70 °C for 20 min, the mixture was allowed to cool and evaporate naturally. Yellow block crystals suitable for single-crystal X-ray diffraction were obtained by evaporating the mixture at room temperature for a period of two weeks. Analysis found: C 65.3, H 4.4, N 30.3%; C15H12N6 requires: C 65.21, H 4.38, N 30.42%.
All H atoms were visible in difference Fourier maps but were placed in calculated positions with C—H= 0.93 Å (CH) or N—H= 0.90 Å (NH), Uiso(H)= 1.2 times Ueq(C) or Ueq(N) for CH or NH. All other non-H atoms were refined anisotropically. The maximum positive peak of 0.26 e Å-3 in the final difference electron density map was located 0.73 Å from atom C5. As the absolute structure cannot been determined for a light atom structure with Mo K-α radiation under normal circumstances, the Friedel-pair reflections have been merged before final refinement.
Recently, there has been much interest in the study of crystal engineering of supramolecular architectures using N-donor ligands (Zheng et al., 2003; Peng et al., 2006). The title compound, C15H12N6, can be an important organic tri- or polydentate ligand to form new metal complexes.
The asymmetric unit (Fig. 1), which contains one molecule. Molecules are linked together via intermolecular N—H···N hydrogen bond interactions (Table. 1). The intermolecular N—H···N contacts (2.856 (3)–2.961 (3) Å) satisfy the definition of standard hydrogen bonds and resulted in a three dimensional supramolecular network (Fig. 2). Interestingly, all of the non-H atoms in the title compound are not coplanar (the mean deviation of the atoms from the least-squares plane is 0.153 Å).
For related literature, see: Peng et al. (2006); Pleier et al. (2001); Zheng et al. (2003).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.
C15H12N6 | Dx = 1.427 Mg m−3 |
Mr = 276.31 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, Pna21 | Cell parameters from 864 reflections |
a = 8.183 (5) Å | θ = 3.7–22.8° |
b = 17.128 (5) Å | µ = 0.09 mm−1 |
c = 9.173 (5) Å | T = 293 K |
V = 1285.7 (11) Å3 | Block, yellow |
Z = 4 | 0.43 × 0.28 × 0.27 mm |
F(000) = 576 |
Bruker SMART APEX II CCD diffractometer | 1670 independent reflections |
Radiation source: fine-focus sealed tube | 1342 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→9 |
Tmin = 0.962, Tmax = 0.976 | k = −19→21 |
7598 measured reflections | l = −12→11 |
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)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.112 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.0158P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
1670 reflections | Δρmax = 0.26 e Å−3 |
190 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Absolute structure: Flack (1983), Number of Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 10 (10) |
C15H12N6 | V = 1285.7 (11) Å3 |
Mr = 276.31 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 8.183 (5) Å | µ = 0.09 mm−1 |
b = 17.128 (5) Å | T = 293 K |
c = 9.173 (5) Å | 0.43 × 0.28 × 0.27 mm |
Bruker SMART APEX II CCD diffractometer | 1670 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 1342 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.976 | Rint = 0.037 |
7598 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.112 | Δρmax = 0.26 e Å−3 |
S = 1.03 | Δρmin = −0.18 e Å−3 |
1670 reflections | Absolute structure: Flack (1983), Number of Friedel pairs? |
190 parameters | Absolute structure parameter: 10 (10) |
1 restraint |
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 | ||
C1 | 0.3602 (3) | 0.18881 (14) | 0.5920 (3) | 0.0366 (5) | |
C2 | 0.3385 (3) | 0.26016 (13) | 0.5217 (3) | 0.0369 (5) | |
H2 | 0.3054 | 0.2612 | 0.4247 | 0.044* | |
C3 | 0.3662 (3) | 0.33028 (14) | 0.5959 (3) | 0.0374 (6) | |
C4 | 0.4121 (3) | 0.32782 (14) | 0.7426 (3) | 0.0383 (6) | |
H4 | 0.4291 | 0.3742 | 0.7929 | 0.046* | |
C5 | 0.4326 (3) | 0.25690 (13) | 0.8144 (3) | 0.0378 (6) | |
C6 | 0.4073 (3) | 0.18830 (14) | 0.7377 (3) | 0.0393 (6) | |
H6 | 0.4221 | 0.1407 | 0.7848 | 0.047* | |
C7 | 0.3371 (3) | 0.11425 (14) | 0.5129 (2) | 0.0359 (5) | |
C8 | 0.4001 (4) | 0.04043 (15) | 0.5471 (3) | 0.0473 (7) | |
H8 | 0.4687 | 0.0274 | 0.6241 | 0.057* | |
C9 | 0.3388 (4) | −0.00815 (16) | 0.4426 (3) | 0.0513 (7) | |
H9 | 0.3563 | −0.0617 | 0.4369 | 0.062* | |
C10 | 0.3529 (3) | 0.40462 (14) | 0.5151 (3) | 0.0372 (5) | |
C11 | 0.3294 (3) | 0.41669 (15) | 0.3655 (3) | 0.0446 (6) | |
H11 | 0.3131 | 0.3787 | 0.2945 | 0.053* | |
C12 | 0.3355 (4) | 0.49591 (16) | 0.3455 (3) | 0.0486 (7) | |
H12 | 0.3255 | 0.5221 | 0.2571 | 0.058* | |
C13 | 0.4818 (3) | 0.25235 (13) | 0.9689 (3) | 0.0373 (5) | |
C14 | 0.4694 (3) | 0.18895 (14) | 1.0637 (3) | 0.0435 (6) | |
H14 | 0.4265 | 0.1400 | 1.0427 | 0.052* | |
C15 | 0.5333 (3) | 0.21336 (15) | 1.1941 (3) | 0.0444 (6) | |
H15 | 0.5424 | 0.1837 | 1.2787 | 0.053* | |
N1 | 0.2498 (3) | 0.03384 (13) | 0.3505 (3) | 0.0482 (6) | |
H1 | 0.2004 | 0.0152 | 0.2754 | 0.058* | |
N2 | 0.2472 (3) | 0.11020 (12) | 0.3905 (2) | 0.0428 (5) | |
N3 | 0.3585 (3) | 0.52856 (13) | 0.4757 (3) | 0.0538 (6) | |
H3 | 0.3642 | 0.5780 | 0.4908 | 0.065* | |
N4 | 0.3717 (3) | 0.47320 (13) | 0.5816 (2) | 0.0478 (6) | |
N5 | 0.5799 (3) | 0.28760 (13) | 1.1773 (2) | 0.0469 (6) | |
H5 | 0.6233 | 0.3156 | 1.2448 | 0.056* | |
N6 | 0.5498 (3) | 0.31309 (11) | 1.0397 (2) | 0.0444 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0490 (13) | 0.0301 (12) | 0.0306 (12) | −0.0023 (10) | −0.0015 (10) | −0.0039 (10) |
C2 | 0.0520 (14) | 0.0333 (13) | 0.0253 (11) | −0.0002 (10) | −0.0035 (10) | −0.0033 (10) |
C3 | 0.0473 (13) | 0.0303 (12) | 0.0347 (13) | 0.0015 (10) | −0.0005 (11) | −0.0027 (10) |
C4 | 0.0538 (14) | 0.0292 (13) | 0.0320 (12) | −0.0017 (10) | −0.0050 (11) | −0.0058 (10) |
C5 | 0.0476 (13) | 0.0352 (14) | 0.0306 (13) | −0.0021 (10) | −0.0036 (11) | −0.0037 (9) |
C6 | 0.0581 (15) | 0.0308 (13) | 0.0292 (12) | −0.0004 (10) | −0.0058 (11) | −0.0008 (10) |
C7 | 0.0517 (13) | 0.0298 (12) | 0.0261 (11) | −0.0020 (10) | −0.0010 (10) | −0.0018 (10) |
C8 | 0.0674 (17) | 0.0356 (13) | 0.0389 (14) | 0.0061 (12) | −0.0106 (13) | −0.0025 (11) |
C9 | 0.0731 (18) | 0.0324 (14) | 0.0485 (17) | 0.0068 (13) | −0.0084 (14) | −0.0068 (13) |
C10 | 0.0472 (13) | 0.0301 (12) | 0.0344 (12) | 0.0014 (10) | −0.0004 (11) | −0.0037 (10) |
C11 | 0.0618 (16) | 0.0363 (14) | 0.0356 (13) | −0.0012 (11) | −0.0063 (13) | −0.0054 (11) |
C12 | 0.0675 (17) | 0.0423 (15) | 0.0361 (13) | −0.0018 (13) | −0.0035 (12) | 0.0056 (12) |
C13 | 0.0489 (13) | 0.0331 (13) | 0.0299 (12) | −0.0017 (10) | −0.0030 (11) | −0.0043 (9) |
C14 | 0.0592 (16) | 0.0308 (12) | 0.0405 (15) | −0.0041 (11) | −0.0026 (12) | −0.0006 (11) |
C15 | 0.0564 (15) | 0.0408 (14) | 0.0361 (14) | 0.0013 (12) | 0.0006 (12) | 0.0026 (12) |
N1 | 0.0695 (15) | 0.0361 (13) | 0.0389 (11) | −0.0025 (10) | −0.0096 (11) | −0.0085 (9) |
N2 | 0.0653 (14) | 0.0327 (11) | 0.0303 (11) | −0.0027 (10) | −0.0084 (10) | −0.0034 (9) |
N3 | 0.0862 (17) | 0.0317 (12) | 0.0436 (13) | −0.0032 (11) | 0.0032 (13) | 0.0023 (10) |
N4 | 0.0768 (16) | 0.0301 (11) | 0.0364 (12) | −0.0014 (10) | 0.0042 (12) | −0.0023 (9) |
N5 | 0.0678 (15) | 0.0413 (12) | 0.0316 (11) | −0.0026 (10) | −0.0083 (11) | −0.0051 (10) |
N6 | 0.0699 (15) | 0.0327 (10) | 0.0307 (11) | −0.0049 (10) | −0.0084 (11) | −0.0028 (9) |
C1—C6 | 1.392 (3) | C10—N4 | 1.332 (3) |
C1—C2 | 1.393 (3) | C10—C11 | 1.401 (4) |
C1—C7 | 1.481 (3) | C11—C12 | 1.370 (3) |
C2—C3 | 1.399 (3) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—N3 | 1.332 (4) |
C3—C4 | 1.397 (3) | C12—H12 | 0.9300 |
C3—C10 | 1.477 (3) | C13—N6 | 1.347 (3) |
C4—C5 | 1.392 (3) | C13—C14 | 1.395 (3) |
C4—H4 | 0.9300 | C14—C15 | 1.371 (4) |
C5—C6 | 1.385 (3) | C14—H14 | 0.9300 |
C5—C13 | 1.475 (4) | C15—N5 | 1.337 (4) |
C6—H6 | 0.9300 | C15—H15 | 0.9300 |
C7—N2 | 1.344 (3) | N1—N2 | 1.358 (3) |
C7—C8 | 1.401 (3) | N1—H1 | 0.8600 |
C8—C9 | 1.365 (4) | N3—N4 | 1.362 (3) |
C8—H8 | 0.9300 | N3—H3 | 0.8600 |
C9—N1 | 1.327 (3) | N5—N6 | 1.358 (3) |
C9—H9 | 0.9300 | N5—H5 | 0.8600 |
C6—C1—C2 | 119.0 (2) | C11—C10—C3 | 129.0 (2) |
C6—C1—C7 | 120.1 (2) | C12—C11—C10 | 105.8 (2) |
C2—C1—C7 | 120.9 (2) | C12—C11—H11 | 127.1 |
C1—C2—C3 | 120.5 (2) | C10—C11—H11 | 127.1 |
C1—C2—H2 | 119.8 | N3—C12—C11 | 107.5 (3) |
C3—C2—H2 | 119.8 | N3—C12—H12 | 126.3 |
C4—C3—C2 | 119.1 (2) | C11—C12—H12 | 126.3 |
C4—C3—C10 | 121.9 (2) | N6—C13—C14 | 109.3 (2) |
C2—C3—C10 | 118.9 (2) | N6—C13—C5 | 122.4 (2) |
C5—C4—C3 | 121.0 (2) | C14—C13—C5 | 128.4 (2) |
C5—C4—H4 | 119.5 | C15—C14—C13 | 106.2 (2) |
C3—C4—H4 | 119.5 | C15—C14—H14 | 126.9 |
C6—C5—C4 | 118.8 (2) | C13—C14—H14 | 126.9 |
C6—C5—C13 | 118.9 (2) | N5—C15—C14 | 107.4 (2) |
C4—C5—C13 | 122.3 (2) | N5—C15—H15 | 126.3 |
C5—C6—C1 | 121.6 (2) | C14—C15—H15 | 126.3 |
C5—C6—H6 | 119.2 | C9—N1—N2 | 111.0 (2) |
C1—C6—H6 | 119.2 | C9—N1—H1 | 124.5 |
N2—C7—C8 | 110.0 (2) | N2—N1—H1 | 124.5 |
N2—C7—C1 | 121.6 (2) | C7—N2—N1 | 105.46 (19) |
C8—C7—C1 | 128.4 (2) | C12—N3—N4 | 111.0 (2) |
C9—C8—C7 | 104.9 (2) | C12—N3—H3 | 124.5 |
C9—C8—H8 | 127.5 | N4—N3—H3 | 124.5 |
C7—C8—H8 | 127.5 | C10—N4—N3 | 106.1 (2) |
N1—C9—C8 | 108.6 (2) | C15—N5—N6 | 111.2 (2) |
N1—C9—H9 | 125.7 | C15—N5—H5 | 124.4 |
C8—C9—H9 | 125.7 | N6—N5—H5 | 124.4 |
N4—C10—C11 | 109.5 (2) | C13—N6—N5 | 106.0 (2) |
N4—C10—C3 | 121.4 (2) | ||
C6—C1—C2—C3 | 1.0 (4) | N4—C10—C11—C12 | 0.1 (3) |
C7—C1—C2—C3 | −177.7 (2) | C3—C10—C11—C12 | −176.5 (2) |
C1—C2—C3—C4 | −1.6 (4) | C10—C11—C12—N3 | −0.9 (3) |
C1—C2—C3—C10 | 175.9 (2) | C6—C5—C13—N6 | 162.0 (3) |
C2—C3—C4—C5 | 1.0 (4) | C4—C5—C13—N6 | −17.4 (4) |
C10—C3—C4—C5 | −176.4 (2) | C6—C5—C13—C14 | −17.5 (4) |
C3—C4—C5—C6 | 0.2 (4) | C4—C5—C13—C14 | 163.0 (3) |
C3—C4—C5—C13 | 179.7 (3) | N6—C13—C14—C15 | −0.4 (3) |
C4—C5—C6—C1 | −0.8 (4) | C5—C13—C14—C15 | 179.2 (3) |
C13—C5—C6—C1 | 179.7 (3) | C13—C14—C15—N5 | 0.4 (3) |
C2—C1—C6—C5 | 0.2 (4) | C8—C9—N1—N2 | −0.7 (3) |
C7—C1—C6—C5 | 178.9 (2) | C8—C7—N2—N1 | 1.7 (3) |
C6—C1—C7—N2 | 159.7 (2) | C1—C7—N2—N1 | −178.7 (2) |
C2—C1—C7—N2 | −21.6 (4) | C9—N1—N2—C7 | −0.6 (3) |
C6—C1—C7—C8 | −20.7 (4) | C11—C12—N3—N4 | 1.4 (3) |
C2—C1—C7—C8 | 158.0 (3) | C11—C10—N4—N3 | 0.7 (3) |
N2—C7—C8—C9 | −2.1 (3) | C3—C10—N4—N3 | 177.6 (2) |
C1—C7—C8—C9 | 178.3 (2) | C12—N3—N4—C10 | −1.3 (3) |
C7—C8—C9—N1 | 1.7 (3) | C14—C15—N5—N6 | −0.3 (3) |
C4—C3—C10—N4 | −5.3 (4) | C14—C13—N6—N5 | 0.2 (3) |
C2—C3—C10—N4 | 177.3 (2) | C5—C13—N6—N5 | −179.4 (2) |
C4—C3—C10—C11 | 171.0 (3) | C15—N5—N6—C13 | 0.1 (3) |
C2—C3—C10—C11 | −6.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N2i | 0.86 | 2.10 | 2.960 (3) | 173 |
N3—H3···N6ii | 0.86 | 2.04 | 2.875 (3) | 163 |
N1—H1···N4iii | 0.86 | 2.01 | 2.855 (3) | 169 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1; (ii) −x+1, −y+1, z−1/2; (iii) −x+1/2, y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H12N6 |
Mr | 276.31 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 293 |
a, b, c (Å) | 8.183 (5), 17.128 (5), 9.173 (5) |
V (Å3) | 1285.7 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.28 × 0.27 |
Data collection | |
Diffractometer | Bruker SMART APEX II CCD |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.962, 0.976 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7598, 1670, 1342 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.112, 1.03 |
No. of reflections | 1670 |
No. of parameters | 190 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.26, −0.18 |
Absolute structure | Flack (1983), Number of Friedel pairs? |
Absolute structure parameter | 10 (10) |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT, SHELXTL (Sheldrick, 2001), SHELXTL and local programs.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5···N2i | 0.86 | 2.10 | 2.960 (3) | 173.2 |
N3—H3···N6ii | 0.86 | 2.04 | 2.875 (3) | 162.5 |
N1—H1···N4iii | 0.86 | 2.01 | 2.855 (3) | 168.7 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1; (ii) −x+1, −y+1, z−1/2; (iii) −x+1/2, y−1/2, z−1/2. |
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Recently, there has been much interest in the study of crystal engineering of supramolecular architectures using N-donor ligands (Zheng et al., 2003; Peng et al., 2006). The title compound, C15H12N6, can be an important organic tri- or polydentate ligand to form new metal complexes.
The asymmetric unit (Fig. 1), which contains one molecule. Molecules are linked together via intermolecular N—H···N hydrogen bond interactions (Table. 1). The intermolecular N—H···N contacts (2.856 (3)–2.961 (3) Å) satisfy the definition of standard hydrogen bonds and resulted in a three dimensional supramolecular network (Fig. 2). Interestingly, all of the non-H atoms in the title compound are not coplanar (the mean deviation of the atoms from the least-squares plane is 0.153 Å).