Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026931/lh2398sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026931/lh2398Isup2.hkl |
CCDC reference: 654884
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.002 Å
- R factor = 0.040
- wR factor = 0.112
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 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 0 ALERT type 5 Informative message, check
The title compound was prepared by 3-amino-1-H-1,2,4-trizole (22 mmol) and p-acetamino benzene solfonyl chloride (25 mmol) in dry pyridine for 3 h. 3-amino-1-H -1,2,4-trizole was prepared by reacting aminoguanidine bicarbonate (250 mmol) and formic acid (17 mL) for 5 h. Then p-acetamino benzene solfonyl chloride was prepared from chlorosofonic acid (0.2 mol) and acetanilide (0.07 mol) in ice water bath. The solid product was collected by filtration. Single crystals suitable for crystallographic analysis were obtained by slow evaporation of a saturated THF-CH3OH(1:1) solution of the title compound at room temperature.
All the H-atoms were discernible in the difference Fourier map but H atoms bound to C atoms were included in calculated positions and allowed to ride during refinement, with C–H = 0.93—0.96 Å and U iso(H) = 1.2U eq (C of aromatic) or 1.5U eq(C of methyl). H atoms bound to N atoms were located in a difference Fourier map and refined with restraints for N—H = 0.86 (1) Å, and Uiso(H) = 1.2Ueq(N).
The title molecule can easily form complexes with copper due to it containing many hetero atoms, so it can act as a type of copper corrosion inhibitor (Sherif et al., 2007). Theoretically, the protons on atom N5 are more active than the proton on atom N2, therefore, when p-acetylamidobenzenesulfonyl chloride reacts with 3-amino-1,2,4-trizole, it should be the active proton which reacts first react (Mai, 2001), but in our experiment, the proton at atom N2 is involved in the reaction. This X-ray study denied the previously molecular structure referred to in the literature. Therefore, the activity of proton N5 under this condition is more active than the proton N2.
For related literature, see: Mai (2001); Sherif et al. (2007).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Bruker, 2000).
Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at the 50% probability level. | |
Fig. 2. The packing of the title molecule with hydrogen bonds shown as dashed lines. |
C10H11N5O3S | F(000) = 584 |
Mr = 281.30 | Dx = 1.547 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6534 reflections |
a = 7.6520 (5) Å | θ = 2.3–28.2° |
b = 11.2724 (8) Å | µ = 0.28 mm−1 |
c = 14.0331 (10) Å | T = 299 K |
β = 94.047 (1)° | Block, colorless |
V = 1207.43 (14) Å3 | 0.30 × 0.30 × 0.25 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 2744 independent reflections |
Radiation source: fine-focus sealed tube | 2513 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 27.5°, θmin = 2.3° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −9→9 |
Tmin = 0.920, Tmax = 0.933 | k = −8→14 |
9872 measured reflections | l = −18→18 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0659P)2 + 0.3863P] where P = (Fo2 + 2Fc2)/3 |
2744 reflections | (Δ/σ)max = 0.045 |
182 parameters | Δρmax = 0.28 e Å−3 |
3 restraints | Δρmin = −0.35 e Å−3 |
C10H11N5O3S | V = 1207.43 (14) Å3 |
Mr = 281.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.6520 (5) Å | µ = 0.28 mm−1 |
b = 11.2724 (8) Å | T = 299 K |
c = 14.0331 (10) Å | 0.30 × 0.30 × 0.25 mm |
β = 94.047 (1)° |
Bruker APEX CCD area-detector diffractometer | 2744 independent reflections |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | 2513 reflections with I > 2σ(I) |
Tmin = 0.920, Tmax = 0.933 | Rint = 0.022 |
9872 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 3 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.28 e Å−3 |
2744 reflections | Δρmin = −0.35 e Å−3 |
182 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 | ||
C1 | 0.4554 (3) | 0.16048 (18) | −0.09977 (14) | 0.0562 (5) | |
H1A | 0.5714 | 0.1277 | −0.0965 | 0.084* | |
H1B | 0.4347 | 0.2040 | −0.1583 | 0.084* | |
H1C | 0.3713 | 0.0975 | −0.0977 | 0.084* | |
C2 | 0.4378 (2) | 0.24186 (16) | −0.01687 (11) | 0.0408 (3) | |
C3 | 0.29405 (19) | 0.43052 (14) | 0.02422 (10) | 0.0373 (3) | |
C4 | 0.3081 (3) | 0.41761 (19) | 0.12380 (12) | 0.0566 (5) | |
H4 | 0.3579 | 0.3496 | 0.1516 | 0.068* | |
C5 | 0.2474 (3) | 0.50655 (19) | 0.18019 (11) | 0.0571 (5) | |
H5 | 0.2568 | 0.4984 | 0.2463 | 0.069* | |
C6 | 0.1727 (2) | 0.60772 (14) | 0.13931 (10) | 0.0373 (3) | |
C7 | 0.1588 (2) | 0.62137 (14) | 0.04080 (10) | 0.0392 (3) | |
H7 | 0.1078 | 0.6892 | 0.0133 | 0.047* | |
C8 | 0.2210 (2) | 0.53344 (15) | −0.01580 (10) | 0.0402 (3) | |
H8 | 0.2142 | 0.5431 | −0.0818 | 0.048* | |
C9 | −0.00719 (19) | 0.60099 (13) | 0.37182 (9) | 0.0336 (3) | |
C10 | −0.2654 (2) | 0.56760 (16) | 0.31668 (12) | 0.0456 (4) | |
H10 | −0.3798 | 0.5393 | 0.3138 | 0.055* | |
N1 | 0.34335 (18) | 0.34180 (13) | −0.03806 (9) | 0.0421 (3) | |
H1 | 0.306 (3) | 0.3514 (19) | −0.0966 (8) | 0.051* | |
N2 | −0.03538 (17) | 0.65192 (12) | 0.28261 (8) | 0.0366 (3) | |
N3 | −0.20576 (18) | 0.62626 (13) | 0.24615 (9) | 0.0423 (3) | |
N4 | −0.15328 (17) | 0.54938 (13) | 0.39494 (9) | 0.0417 (3) | |
N5 | 0.14407 (18) | 0.60225 (14) | 0.42474 (9) | 0.0437 (3) | |
H5A | 0.229 (2) | 0.6426 (17) | 0.4060 (14) | 0.052* | |
H5B | 0.152 (3) | 0.5649 (16) | 0.4789 (9) | 0.052* | |
O1 | 0.50430 (17) | 0.21926 (12) | 0.06242 (9) | 0.0529 (3) | |
O2 | 0.23927 (18) | 0.76165 (12) | 0.27614 (9) | 0.0534 (3) | |
O3 | −0.00441 (18) | 0.80197 (11) | 0.15504 (9) | 0.0508 (3) | |
S1 | 0.09973 (5) | 0.72107 (3) | 0.21183 (2) | 0.03818 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0618 (11) | 0.0550 (11) | 0.0515 (10) | 0.0085 (9) | 0.0010 (8) | −0.0103 (8) |
C2 | 0.0335 (7) | 0.0481 (9) | 0.0405 (8) | −0.0008 (6) | 0.0015 (6) | −0.0006 (7) |
C3 | 0.0349 (7) | 0.0459 (8) | 0.0307 (7) | −0.0005 (6) | −0.0005 (5) | 0.0010 (6) |
C4 | 0.0801 (12) | 0.0578 (11) | 0.0315 (8) | 0.0267 (10) | 0.0008 (8) | 0.0082 (7) |
C5 | 0.0819 (13) | 0.0631 (11) | 0.0261 (7) | 0.0244 (10) | 0.0012 (7) | 0.0068 (7) |
C6 | 0.0406 (7) | 0.0423 (8) | 0.0291 (7) | −0.0013 (6) | 0.0019 (5) | 0.0021 (6) |
C7 | 0.0479 (8) | 0.0387 (8) | 0.0306 (7) | −0.0020 (6) | −0.0005 (6) | 0.0085 (6) |
C8 | 0.0476 (8) | 0.0466 (9) | 0.0260 (6) | −0.0036 (7) | −0.0003 (6) | 0.0056 (6) |
C9 | 0.0435 (7) | 0.0310 (7) | 0.0263 (6) | 0.0021 (6) | 0.0022 (5) | −0.0011 (5) |
C10 | 0.0410 (8) | 0.0545 (10) | 0.0407 (8) | −0.0060 (7) | −0.0015 (6) | 0.0078 (7) |
N1 | 0.0452 (7) | 0.0503 (8) | 0.0300 (6) | 0.0050 (6) | −0.0035 (5) | −0.0010 (6) |
N2 | 0.0399 (6) | 0.0422 (7) | 0.0273 (6) | −0.0029 (5) | 0.0006 (5) | 0.0037 (5) |
N3 | 0.0406 (7) | 0.0517 (8) | 0.0337 (6) | −0.0033 (6) | −0.0035 (5) | 0.0044 (6) |
N4 | 0.0430 (7) | 0.0478 (8) | 0.0341 (6) | −0.0019 (6) | 0.0019 (5) | 0.0072 (5) |
N5 | 0.0452 (7) | 0.0522 (8) | 0.0325 (6) | −0.0082 (6) | −0.0046 (5) | 0.0081 (6) |
O1 | 0.0503 (7) | 0.0638 (8) | 0.0435 (6) | 0.0151 (6) | −0.0052 (5) | 0.0021 (6) |
O2 | 0.0607 (8) | 0.0573 (8) | 0.0416 (6) | −0.0213 (6) | −0.0002 (6) | −0.0023 (6) |
O3 | 0.0710 (8) | 0.0382 (6) | 0.0436 (6) | 0.0053 (6) | 0.0060 (6) | 0.0099 (5) |
S1 | 0.0479 (2) | 0.0357 (2) | 0.0309 (2) | −0.00552 (15) | 0.00257 (16) | 0.00326 (13) |
C1—C2 | 1.495 (2) | C7—H7 | 0.9300 |
C1—H1A | 0.9600 | C8—H8 | 0.9300 |
C1—H1B | 0.9600 | C9—N4 | 1.321 (2) |
C1—H1C | 0.9600 | C9—N5 | 1.3304 (19) |
C2—O1 | 1.217 (2) | C9—N2 | 1.3803 (17) |
C2—N1 | 1.360 (2) | C10—N3 | 1.299 (2) |
C3—C8 | 1.389 (2) | C10—N4 | 1.361 (2) |
C3—N1 | 1.397 (2) | C10—H10 | 0.9300 |
C3—C4 | 1.402 (2) | N1—H1 | 0.857 (9) |
C4—C5 | 1.378 (3) | N2—N3 | 1.3968 (18) |
C4—H4 | 0.9300 | N2—S1 | 1.6757 (13) |
C5—C6 | 1.382 (2) | N5—H5A | 0.852 (9) |
C5—H5 | 0.9300 | N5—H5B | 0.867 (9) |
C6—C7 | 1.3876 (19) | O2—S1 | 1.4240 (13) |
C6—S1 | 1.7494 (16) | O3—S1 | 1.4185 (12) |
C7—C8 | 1.376 (2) | ||
C2—C1—H1A | 109.5 | C7—C8—H8 | 119.5 |
C2—C1—H1B | 109.5 | C3—C8—H8 | 119.5 |
H1A—C1—H1B | 109.5 | N4—C9—N5 | 125.85 (13) |
C2—C1—H1C | 109.5 | N4—C9—N2 | 108.98 (13) |
H1A—C1—H1C | 109.5 | N5—C9—N2 | 125.16 (14) |
H1B—C1—H1C | 109.5 | N3—C10—N4 | 117.16 (15) |
O1—C2—N1 | 123.68 (16) | N3—C10—H10 | 121.4 |
O1—C2—C1 | 121.88 (16) | N4—C10—H10 | 121.4 |
N1—C2—C1 | 114.44 (14) | C2—N1—C3 | 128.23 (13) |
C8—C3—N1 | 117.61 (13) | C2—N1—H1 | 116.7 (14) |
C8—C3—C4 | 119.35 (15) | C3—N1—H1 | 115.0 (14) |
N1—C3—C4 | 122.97 (15) | C9—N2—N3 | 109.16 (12) |
C5—C4—C3 | 119.46 (16) | C9—N2—S1 | 131.89 (11) |
C5—C4—H4 | 120.3 | N3—N2—S1 | 118.56 (9) |
C3—C4—H4 | 120.3 | C10—N3—N2 | 101.25 (12) |
C4—C5—C6 | 120.55 (14) | C9—N4—C10 | 103.39 (13) |
C4—C5—H5 | 119.7 | C9—N5—H5A | 119.2 (14) |
C6—C5—H5 | 119.7 | C9—N5—H5B | 119.4 (13) |
C5—C6—C7 | 120.37 (15) | H5A—N5—H5B | 121.3 (19) |
C5—C6—S1 | 120.06 (11) | O3—S1—O2 | 121.05 (8) |
C7—C6—S1 | 119.55 (12) | O3—S1—N2 | 106.64 (7) |
C8—C7—C6 | 119.32 (14) | O2—S1—N2 | 103.89 (7) |
C8—C7—H7 | 120.3 | O3—S1—C6 | 109.43 (7) |
C6—C7—H7 | 120.3 | O2—S1—C6 | 110.33 (8) |
C7—C8—C3 | 120.93 (13) | N2—S1—C6 | 103.93 (7) |
C8—C3—C4—C5 | 0.7 (3) | N4—C10—N3—N2 | −1.2 (2) |
N1—C3—C4—C5 | −176.32 (19) | C9—N2—N3—C10 | 2.35 (17) |
C3—C4—C5—C6 | 0.2 (3) | S1—N2—N3—C10 | 176.00 (12) |
C4—C5—C6—C7 | −0.4 (3) | N5—C9—N4—C10 | −176.97 (16) |
C4—C5—C6—S1 | −178.89 (17) | N2—C9—N4—C10 | 1.91 (18) |
C5—C6—C7—C8 | −0.4 (2) | N3—C10—N4—C9 | −0.4 (2) |
S1—C6—C7—C8 | 178.12 (12) | C9—N2—S1—O3 | −152.26 (14) |
C6—C7—C8—C3 | 1.4 (2) | N3—N2—S1—O3 | 35.81 (13) |
N1—C3—C8—C7 | 175.68 (14) | C9—N2—S1—O2 | −23.32 (16) |
C4—C3—C8—C7 | −1.5 (3) | N3—N2—S1—O2 | 164.76 (12) |
O1—C2—N1—C3 | −4.9 (3) | C9—N2—S1—C6 | 92.15 (15) |
C1—C2—N1—C3 | 175.40 (16) | N3—N2—S1—C6 | −79.77 (13) |
C8—C3—N1—C2 | 170.17 (15) | C5—C6—S1—O3 | −167.40 (15) |
C4—C3—N1—C2 | −12.7 (3) | C7—C6—S1—O3 | 14.06 (15) |
N4—C9—N2—N3 | −2.79 (17) | C5—C6—S1—O2 | 57.04 (17) |
N5—C9—N2—N3 | 176.09 (15) | C7—C6—S1—O2 | −121.49 (13) |
N4—C9—N2—S1 | −175.29 (12) | C5—C6—S1—N2 | −53.79 (16) |
N5—C9—N2—S1 | 3.6 (2) | C7—C6—S1—N2 | 127.67 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.86 (1) | 2.20 (1) | 3.0547 (18) | 179 (2) |
N5—H5A···O1ii | 0.85 (1) | 2.23 (1) | 2.9906 (19) | 149 (2) |
N5—H5B···N4iii | 0.87 (1) | 2.19 (1) | 3.0503 (18) | 172 (2) |
N5—H5A···O2 | 0.85 (1) | 2.27 (2) | 2.8848 (19) | 129 (2) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C10H11N5O3S |
Mr | 281.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 7.6520 (5), 11.2724 (8), 14.0331 (10) |
β (°) | 94.047 (1) |
V (Å3) | 1207.43 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.28 |
Crystal size (mm) | 0.30 × 0.30 × 0.25 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan SADABS (Sheldrick, 1996) |
Tmin, Tmax | 0.920, 0.933 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9872, 2744, 2513 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.112, 1.04 |
No. of reflections | 2744 |
No. of parameters | 182 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.35 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···N3i | 0.857 (9) | 2.198 (10) | 3.0547 (18) | 179 (2) |
N5—H5A···O1ii | 0.852 (9) | 2.230 (13) | 2.9906 (19) | 148.8 (18) |
N5—H5B···N4iii | 0.867 (9) | 2.189 (10) | 3.0503 (18) | 172.0 (19) |
N5—H5A···O2 | 0.852 (9) | 2.269 (17) | 2.8848 (19) | 129.3 (17) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, −y+1, −z+1. |
The title molecule can easily form complexes with copper due to it containing many hetero atoms, so it can act as a type of copper corrosion inhibitor (Sherif et al., 2007). Theoretically, the protons on atom N5 are more active than the proton on atom N2, therefore, when p-acetylamidobenzenesulfonyl chloride reacts with 3-amino-1,2,4-trizole, it should be the active proton which reacts first react (Mai, 2001), but in our experiment, the proton at atom N2 is involved in the reaction. This X-ray study denied the previously molecular structure referred to in the literature. Therefore, the activity of proton N5 under this condition is more active than the proton N2.