Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045473/hb2543sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045473/hb2543Isup2.hkl |
CCDC reference: 663815
Key indicators
- Single-crystal X-ray study
- T = 153 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.095
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.94 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT322_ALERT_2_C Check Hybridisation of S2 in Main Residue . ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.937 Tmax scaled 0.937 Tmin scaled 0.921
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The title compound, was obtained by the reaction of 2-aminothiadiazole (5.05 g, 0.05 mmol) and 2-pyridylaldehyde (6.5 g, 0.06 mmol) in 100 ml me thanol solution with ten drops of 6 M HCl. The colorless block crystals of (I) were grown via recrystallization in methanol at room temperature.
The H atoms were positionedg geometrically (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(carrier).
The molecule of the title compound, (I) (Fig. 1), consists of two aminothiadiazolyl rings and a pyridyl group bridged by a carbon atom with the N donors of the pyridyl and thiadiazolyl groups extending toward the same direction. Dihedral angles between rings (identified by one atom) are S1/S2 = 80.91 (10)°, S1/N1 = 87.08 (9)°, S2/N1 = 73.65 (9)°.
In the crystal, adjacent molecules are linked by N—H···N hydrogen bonds (Table 1) to generate a one-dimensional supramolecular network, as shown in Fig. 2. There are no aromatic π-π stacking interactions involving the thiadiazolyl and pridyl rings.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).
C10H9N7S2 | F(000) = 600 |
Mr = 291.36 | Dx = 1.500 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 12640 reflections |
a = 11.283 (2) Å | θ = 3.4–27.5° |
b = 8.7613 (18) Å | µ = 0.41 mm−1 |
c = 13.151 (3) Å | T = 153 K |
β = 97.13 (3)° | Block, colourless |
V = 1290.0 (5) Å3 | 0.20 × 0.18 × 0.16 mm |
Z = 4 |
Bruker P4 diffractometer | 2953 independent reflections |
Radiation source: fine-focus sealed tube | 1908 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −14→14 |
Tmin = 0.983, Tmax = 1.000 | k = −11→11 |
5688 measured reflections | l = −17→17 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0492P)2] where P = (Fo2 + 2Fc2)/3 |
2953 reflections | (Δ/σ)max = 0.001 |
172 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C10H9N7S2 | V = 1290.0 (5) Å3 |
Mr = 291.36 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.283 (2) Å | µ = 0.41 mm−1 |
b = 8.7613 (18) Å | T = 153 K |
c = 13.151 (3) Å | 0.20 × 0.18 × 0.16 mm |
β = 97.13 (3)° |
Bruker P4 diffractometer | 2953 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 1908 reflections with I > 2σ(I) |
Tmin = 0.983, Tmax = 1.000 | Rint = 0.026 |
5688 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.29 e Å−3 |
2953 reflections | Δρmin = −0.33 e Å−3 |
172 parameters |
x | y | z | Uiso*/Ueq | ||
C1 | 0.39112 (15) | 0.06831 (18) | 0.76159 (12) | 0.0325 (4) | |
C2 | 0.55007 (17) | −0.0844 (2) | 0.82008 (16) | 0.0514 (5) | |
H2 | 0.5793 | −0.1714 | 0.8552 | 0.062* | |
C3 | 0.62985 (18) | 0.0092 (2) | 0.77961 (16) | 0.0526 (5) | |
H3 | 0.7109 | −0.0138 | 0.7871 | 0.063* | |
C4 | 0.58714 (18) | 0.1363 (2) | 0.72823 (15) | 0.0508 (5) | |
H4 | 0.6389 | 0.2016 | 0.6996 | 0.061* | |
C5 | 0.46582 (17) | 0.1680 (2) | 0.71879 (13) | 0.0429 (5) | |
H5 | 0.4353 | 0.2549 | 0.6843 | 0.052* | |
C6 | 0.25742 (15) | 0.09060 (19) | 0.75500 (12) | 0.0345 (4) | |
H6 | 0.2199 | −0.0105 | 0.7517 | 0.041* | |
C7 | 0.17955 (14) | 0.10493 (19) | 0.57373 (13) | 0.0345 (4) | |
C8 | 0.1164 (2) | 0.0319 (2) | 0.40249 (15) | 0.0539 (5) | |
H8 | 0.0864 | 0.0218 | 0.3337 | 0.065* | |
C9 | 0.11296 (16) | 0.1562 (2) | 0.86842 (13) | 0.0381 (4) | |
C10 | −0.0725 (2) | 0.1710 (3) | 0.93144 (19) | 0.0695 (7) | |
H10 | −0.1392 | 0.1909 | 0.9644 | 0.083* | |
N1 | 0.43237 (13) | −0.05732 (15) | 0.81182 (12) | 0.0411 (4) | |
N2 | 0.20837 (14) | 0.17587 (16) | 0.66401 (11) | 0.0410 (4) | |
H2A | 0.1978 | 0.2728 | 0.6682 | 0.049* | |
N3 | 0.20509 (14) | −0.03795 (17) | 0.55573 (11) | 0.0433 (4) | |
N4 | 0.16735 (16) | −0.07900 (18) | 0.45482 (12) | 0.0534 (4) | |
N5 | 0.22648 (13) | 0.16712 (16) | 0.84586 (11) | 0.0388 (4) | |
H5A | 0.2792 | 0.2184 | 0.8846 | 0.047* | |
N6 | 0.03642 (14) | 0.05646 (18) | 0.82607 (13) | 0.0496 (4) | |
N7 | −0.07234 (16) | 0.0652 (2) | 0.86360 (15) | 0.0657 (5) | |
S1 | 0.10722 (5) | 0.20038 (6) | 0.46841 (4) | 0.04768 (17) | |
S2 | 0.05728 (5) | 0.27312 (7) | 0.95736 (4) | 0.06054 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0361 (10) | 0.0303 (9) | 0.0306 (9) | −0.0021 (7) | 0.0020 (7) | −0.0041 (7) |
C2 | 0.0401 (12) | 0.0420 (11) | 0.0689 (14) | 0.0063 (9) | −0.0055 (10) | 0.0012 (10) |
C3 | 0.0323 (11) | 0.0615 (14) | 0.0632 (14) | −0.0034 (10) | 0.0028 (10) | −0.0130 (11) |
C4 | 0.0488 (13) | 0.0568 (13) | 0.0484 (12) | −0.0155 (10) | 0.0119 (10) | −0.0039 (10) |
C5 | 0.0491 (12) | 0.0382 (10) | 0.0414 (11) | −0.0061 (9) | 0.0052 (9) | 0.0050 (8) |
C6 | 0.0380 (10) | 0.0303 (9) | 0.0344 (10) | 0.0012 (7) | 0.0018 (7) | −0.0035 (7) |
C7 | 0.0313 (10) | 0.0363 (10) | 0.0358 (10) | 0.0020 (7) | 0.0033 (7) | 0.0017 (8) |
C8 | 0.0639 (14) | 0.0591 (13) | 0.0366 (11) | −0.0043 (11) | −0.0022 (10) | −0.0014 (10) |
C9 | 0.0411 (11) | 0.0380 (10) | 0.0348 (10) | 0.0012 (8) | 0.0026 (8) | −0.0023 (8) |
C10 | 0.0451 (14) | 0.0941 (18) | 0.0721 (16) | −0.0046 (12) | 0.0190 (11) | −0.0144 (14) |
N1 | 0.0385 (9) | 0.0324 (8) | 0.0506 (9) | −0.0012 (7) | −0.0011 (7) | 0.0057 (7) |
N2 | 0.0530 (10) | 0.0298 (8) | 0.0382 (9) | 0.0069 (7) | −0.0023 (7) | −0.0019 (7) |
N3 | 0.0527 (10) | 0.0382 (9) | 0.0376 (9) | 0.0060 (7) | −0.0001 (7) | −0.0035 (7) |
N4 | 0.0708 (12) | 0.0486 (10) | 0.0386 (10) | −0.0010 (9) | −0.0016 (8) | −0.0094 (8) |
N5 | 0.0344 (9) | 0.0441 (9) | 0.0375 (9) | −0.0054 (7) | 0.0024 (7) | −0.0114 (7) |
N6 | 0.0388 (9) | 0.0554 (10) | 0.0542 (10) | −0.0067 (8) | 0.0042 (8) | −0.0112 (8) |
N7 | 0.0417 (11) | 0.0844 (14) | 0.0713 (13) | −0.0134 (10) | 0.0086 (9) | −0.0122 (11) |
S1 | 0.0522 (3) | 0.0472 (3) | 0.0414 (3) | 0.0072 (2) | −0.0028 (2) | 0.0083 (2) |
S2 | 0.0534 (4) | 0.0723 (4) | 0.0590 (4) | −0.0035 (3) | 0.0191 (3) | −0.0240 (3) |
C1—N1 | 1.337 (2) | C7—N2 | 1.344 (2) |
C1—C5 | 1.382 (2) | C7—S1 | 1.7330 (18) |
C1—C6 | 1.513 (2) | C8—N4 | 1.284 (2) |
C2—N1 | 1.340 (2) | C8—S1 | 1.722 (2) |
C2—C3 | 1.373 (3) | C8—H8 | 0.9300 |
C2—H2 | 0.9300 | C9—N6 | 1.304 (2) |
C3—C4 | 1.360 (3) | C9—N5 | 1.354 (2) |
C3—H3 | 0.9300 | C9—S2 | 1.7307 (18) |
C4—C5 | 1.387 (3) | C10—N7 | 1.287 (3) |
C4—H4 | 0.9300 | C10—S2 | 1.714 (2) |
C5—H5 | 0.9300 | C10—H10 | 0.9300 |
C6—N5 | 1.450 (2) | N2—H2A | 0.8600 |
C6—N2 | 1.460 (2) | N3—N4 | 1.390 (2) |
C6—H6 | 0.9800 | N5—H5A | 0.8600 |
C7—N3 | 1.313 (2) | N6—N7 | 1.380 (2) |
N1—C1—C5 | 121.96 (17) | N2—C7—S1 | 121.42 (13) |
N1—C1—C6 | 114.72 (14) | N4—C8—S1 | 115.44 (15) |
C5—C1—C6 | 123.32 (16) | N4—C8—H8 | 122.3 |
N1—C2—C3 | 123.64 (19) | S1—C8—H8 | 122.3 |
N1—C2—H2 | 118.2 | N6—C9—N5 | 123.27 (16) |
C3—C2—H2 | 118.2 | N6—C9—S2 | 114.12 (14) |
C4—C3—C2 | 118.21 (19) | N5—C9—S2 | 122.60 (13) |
C4—C3—H3 | 120.9 | N7—C10—S2 | 116.03 (17) |
C2—C3—H3 | 120.9 | N7—C10—H10 | 122.0 |
C3—C4—C5 | 119.58 (18) | S2—C10—H10 | 122.0 |
C3—C4—H4 | 120.2 | C1—N1—C2 | 117.80 (16) |
C5—C4—H4 | 120.2 | C7—N2—C6 | 120.86 (14) |
C1—C5—C4 | 118.80 (18) | C7—N2—H2A | 119.6 |
C1—C5—H5 | 120.6 | C6—N2—H2A | 119.6 |
C4—C5—H5 | 120.6 | C7—N3—N4 | 111.77 (15) |
N5—C6—N2 | 109.47 (14) | C8—N4—N3 | 112.31 (15) |
N5—C6—C1 | 110.65 (14) | C9—N5—C6 | 118.61 (14) |
N2—C6—C1 | 112.76 (14) | C9—N5—H5A | 120.7 |
N5—C6—H6 | 107.9 | C6—N5—H5A | 120.7 |
N2—C6—H6 | 107.9 | C9—N6—N7 | 112.40 (16) |
C1—C6—H6 | 107.9 | C10—N7—N6 | 111.47 (18) |
N3—C7—N2 | 124.47 (16) | C8—S1—C7 | 86.39 (10) |
N3—C7—S1 | 114.09 (13) | C10—S2—C9 | 85.96 (11) |
N1—C2—C3—C4 | 0.0 (3) | S1—C7—N3—N4 | 0.01 (19) |
C2—C3—C4—C5 | 0.4 (3) | S1—C8—N4—N3 | 0.0 (2) |
N1—C1—C5—C4 | 0.1 (3) | C7—N3—N4—C8 | 0.0 (2) |
C6—C1—C5—C4 | −179.31 (15) | N6—C9—N5—C6 | 14.7 (3) |
C3—C4—C5—C1 | −0.4 (3) | S2—C9—N5—C6 | −165.92 (13) |
N1—C1—C6—N5 | 85.31 (18) | N2—C6—N5—C9 | 74.84 (19) |
C5—C1—C6—N5 | −95.21 (18) | C1—C6—N5—C9 | −160.28 (14) |
N1—C1—C6—N2 | −151.70 (15) | N5—C9—N6—N7 | 178.40 (17) |
C5—C1—C6—N2 | 27.8 (2) | S2—C9—N6—N7 | −1.1 (2) |
C5—C1—N1—C2 | 0.2 (3) | S2—C10—N7—N6 | 0.5 (3) |
C6—C1—N1—C2 | 179.69 (15) | C9—N6—N7—C10 | 0.4 (3) |
C3—C2—N1—C1 | −0.3 (3) | N4—C8—S1—C7 | 0.04 (17) |
N3—C7—N2—C6 | −8.6 (3) | N3—C7—S1—C8 | −0.03 (15) |
S1—C7—N2—C6 | 173.28 (12) | N2—C7—S1—C8 | 178.31 (15) |
N5—C6—N2—C7 | −151.96 (15) | N7—C10—S2—C9 | −0.9 (2) |
C1—C6—N2—C7 | 84.40 (19) | N6—C9—S2—C10 | 1.09 (16) |
N2—C7—N3—N4 | −178.27 (15) | N5—C9—S2—C10 | −178.39 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.13 | 2.866 (2) | 143 |
N5—H5A···N3i | 0.86 | 2.27 | 2.949 (2) | 136 |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C10H9N7S2 |
Mr | 291.36 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 153 |
a, b, c (Å) | 11.283 (2), 8.7613 (18), 13.151 (3) |
β (°) | 97.13 (3) |
V (Å3) | 1290.0 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.41 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker P4 |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.983, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5688, 2953, 1908 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.03 |
No. of reflections | 2953 |
No. of parameters | 172 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.33 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···N1i | 0.86 | 2.13 | 2.866 (2) | 143 |
N5—H5A···N3i | 0.86 | 2.27 | 2.949 (2) | 136 |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
The molecule of the title compound, (I) (Fig. 1), consists of two aminothiadiazolyl rings and a pyridyl group bridged by a carbon atom with the N donors of the pyridyl and thiadiazolyl groups extending toward the same direction. Dihedral angles between rings (identified by one atom) are S1/S2 = 80.91 (10)°, S1/N1 = 87.08 (9)°, S2/N1 = 73.65 (9)°.
In the crystal, adjacent molecules are linked by N—H···N hydrogen bonds (Table 1) to generate a one-dimensional supramolecular network, as shown in Fig. 2. There are no aromatic π-π stacking interactions involving the thiadiazolyl and pridyl rings.