organic compounds
The title compound, C10H11N3O2S, was designed and synthesized as a potential antitumour agent and a single-crystal X-ray analysis was undertaken to determine the three-dimensional arrangement of the putative pharmacophoric groups. The central pyrazole ring is exactly planar and the 1-phenyl group has no effect on the π-electron system of the pyrazole nucleus. In contrast, the 5-amino N atom is strongly conjugated with the pyrazole ring such that the flow of the resulting negative charge is in the direction of the 4-sulfonyl O atoms. All of the potential hydrogen-bond donors and acceptors are actually involved in hydrogen bonding.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033556/ac6208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033556/ac6208Isup2.hkl |
CCDC reference: 289623
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
Computing details top
Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON92 (Spek, 1992); software used to prepare material for publication: SHELXL97.
5-Amino-4-methylsulfonyl-1-phenyl-1H-pyrazole top
Crystal data top
C10H11N3O2S | F(000) = 496 |
Mr = 237.28 | Dx = 1.445 Mg m−3 |
Monoclinic, P21/n | Melting point: 407 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.083 (2) Å | Cell parameters from 20 reflections |
b = 12.274 (3) Å | θ = 7–20° |
c = 11.040 (3) Å | µ = 0.29 mm−1 |
β = 95.20 (3)° | T = 293 K |
V = 1090.8 (5) Å3 | Prism, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.039 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 2.5° |
Graphite monochromator | h = −1→10 |
ω/2θ scans | k = −1→15 |
3298 measured reflections | l = −14→14 |
2504 independent reflections | 3 standard reflections every 97 reflections |
2080 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3 |
2504 reflections | (Δ/σ)max = 0.001 |
146 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
N1 | 0.58298 (17) | 0.67943 (12) | 0.44428 (12) | 0.0327 (3) | |
N2 | 0.60842 (18) | 0.70948 (13) | 0.56571 (13) | 0.0393 (3) | |
C3 | 0.4813 (2) | 0.77146 (15) | 0.58330 (15) | 0.0375 (4) | |
H3 | 0.4640 | 0.8029 | 0.6578 | 0.045* | |
C4 | 0.37345 (19) | 0.78532 (13) | 0.47696 (14) | 0.0309 (3) | |
C5 | 0.44344 (19) | 0.72442 (13) | 0.38750 (14) | 0.0293 (3) | |
C6 | 0.6987 (2) | 0.60653 (14) | 0.39555 (14) | 0.0332 (3) | |
C7 | 0.8652 (2) | 0.63415 (15) | 0.40759 (17) | 0.0412 (4) | |
H7 | 0.9000 | 0.6995 | 0.4442 | 0.049* | |
C8 | 0.9792 (3) | 0.56350 (18) | 0.3646 (2) | 0.0515 (5) | |
H8 | 1.0916 | 0.5811 | 0.3723 | 0.062* | |
C9 | 0.9269 (3) | 0.46736 (18) | 0.3106 (2) | 0.0559 (5) | |
H9 | 1.0041 | 0.4199 | 0.2819 | 0.067* | |
C10 | 0.7608 (3) | 0.44073 (17) | 0.2984 (2) | 0.0559 (5) | |
H10 | 0.7268 | 0.3756 | 0.2610 | 0.067* | |
C11 | 0.6437 (2) | 0.50997 (16) | 0.34145 (18) | 0.0455 (4) | |
H11 | 0.5315 | 0.4919 | 0.3341 | 0.055* | |
S1 | 0.19650 (5) | 0.86328 (3) | 0.46018 (4) | 0.03279 (14) | |
O1 | 0.11200 (17) | 0.83895 (13) | 0.34374 (12) | 0.0520 (4) | |
O2 | 0.10668 (17) | 0.85023 (12) | 0.56575 (12) | 0.0494 (4) | |
C12 | 0.2621 (3) | 1.00009 (16) | 0.4589 (2) | 0.0505 (5) | |
H12A | 0.3241 | 1.0122 | 0.3900 | 0.076* | |
H12B | 0.3311 | 1.0155 | 0.5323 | 0.076* | |
H12C | 0.1668 | 1.0471 | 0.4537 | 0.076* | |
N3 | 0.39312 (18) | 0.70690 (13) | 0.26915 (13) | 0.0404 (4) | |
H3A | 0.4504 | 0.6655 | 0.2260 | 0.048* | |
H3B | 0.3038 | 0.7371 | 0.2369 | 0.048* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0318 (7) | 0.0383 (7) | 0.0277 (6) | 0.0024 (6) | 0.0012 (5) | −0.0022 (6) |
N2 | 0.0397 (8) | 0.0494 (9) | 0.0278 (7) | 0.0026 (7) | −0.0029 (6) | −0.0029 (6) |
C3 | 0.0407 (9) | 0.0444 (9) | 0.0273 (8) | 0.0005 (7) | 0.0020 (6) | −0.0047 (7) |
C4 | 0.0303 (8) | 0.0353 (8) | 0.0275 (7) | −0.0013 (6) | 0.0038 (6) | −0.0018 (6) |
C5 | 0.0280 (7) | 0.0322 (8) | 0.0279 (7) | −0.0035 (6) | 0.0029 (5) | 0.0008 (6) |
C6 | 0.0349 (8) | 0.0335 (8) | 0.0311 (8) | 0.0033 (6) | 0.0030 (6) | 0.0029 (6) |
C7 | 0.0377 (9) | 0.0427 (9) | 0.0434 (9) | −0.0010 (8) | 0.0049 (7) | 0.0025 (8) |
C8 | 0.0398 (10) | 0.0601 (13) | 0.0561 (12) | 0.0114 (9) | 0.0127 (8) | 0.0119 (10) |
C9 | 0.0664 (14) | 0.0496 (11) | 0.0546 (12) | 0.0221 (10) | 0.0212 (10) | 0.0071 (10) |
C10 | 0.0733 (15) | 0.0378 (10) | 0.0577 (12) | 0.0075 (10) | 0.0123 (11) | −0.0065 (9) |
C11 | 0.0463 (10) | 0.0393 (10) | 0.0509 (11) | −0.0003 (8) | 0.0042 (8) | −0.0036 (8) |
S1 | 0.0264 (2) | 0.0411 (2) | 0.0316 (2) | −0.00034 (16) | 0.00733 (14) | −0.00084 (16) |
O1 | 0.0391 (7) | 0.0732 (10) | 0.0421 (7) | 0.0080 (7) | −0.0054 (6) | −0.0076 (7) |
O2 | 0.0426 (7) | 0.0634 (9) | 0.0455 (8) | 0.0007 (6) | 0.0223 (6) | 0.0021 (6) |
C12 | 0.0449 (11) | 0.0391 (10) | 0.0690 (14) | 0.0039 (8) | 0.0143 (9) | 0.0054 (9) |
N3 | 0.0385 (8) | 0.0544 (9) | 0.0276 (7) | 0.0108 (7) | −0.0009 (5) | −0.0067 (6) |
Geometric parameters (Å, º) top
N1—C5 | 1.357 (2) | C8—H8 | 0.9300 |
N1—N2 | 1.388 (2) | C9—C10 | 1.376 (3) |
N1—C6 | 1.434 (2) | C9—H9 | 0.9300 |
N2—C3 | 1.307 (2) | C10—C11 | 1.388 (3) |
C3—C4 | 1.408 (2) | C10—H10 | 0.9300 |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.398 (2) | S1—O1 | 1.4314 (14) |
C4—S1 | 1.717 (2) | S1—O2 | 1.4368 (14) |
C5—N3 | 1.350 (2) | S1—C12 | 1.761 (2) |
C6—C7 | 1.383 (2) | C12—H12A | 0.9600 |
C6—C11 | 1.382 (3) | C12—H12B | 0.9600 |
C7—C8 | 1.380 (3) | C12—H12C | 0.9600 |
C7—H7 | 0.9300 | N3—H3A | 0.8600 |
C8—C9 | 1.372 (3) | N3—H3B | 0.8600 |
C5—N1—N2 | 112.47 (13) | C8—C9—H9 | 119.8 |
C5—N1—C6 | 128.59 (14) | C10—C9—H9 | 119.8 |
N2—N1—C6 | 118.93 (13) | C9—C10—C11 | 120.7 (2) |
C3—N2—N1 | 104.39 (13) | C9—C10—H10 | 119.6 |
N2—C3—C4 | 112.46 (15) | C11—C10—H10 | 119.6 |
N2—C3—H3 | 123.8 | C6—C11—C10 | 118.04 (19) |
C4—C3—H3 | 123.8 | C6—C11—H11 | 121.0 |
C5—C4—C3 | 105.36 (14) | C10—C11—H11 | 121.0 |
C5—C4—S1 | 127.45 (12) | O1—S1—O2 | 118.04 (9) |
C3—C4—S1 | 127.17 (13) | O1—S1—C4 | 107.80 (8) |
N3—C5—N1 | 123.17 (15) | O2—S1—C4 | 109.12 (8) |
N3—C5—C4 | 131.53 (15) | O1—S1—C12 | 108.13 (11) |
N1—C5—C4 | 105.29 (14) | O2—S1—C12 | 106.70 (10) |
C7—C6—C11 | 121.60 (17) | C4—S1—C12 | 106.48 (9) |
C7—C6—N1 | 118.25 (16) | S1—C12—H12A | 109.5 |
C11—C6—N1 | 120.11 (16) | S1—C12—H12B | 109.5 |
C8—C7—C6 | 119.16 (18) | H12A—C12—H12B | 109.5 |
C8—C7—H7 | 120.4 | S1—C12—H12C | 109.5 |
C6—C7—H7 | 120.4 | H12A—C12—H12C | 109.5 |
C9—C8—C7 | 120.1 (2) | H12B—C12—H12C | 109.5 |
C9—C8—H8 | 120.0 | C5—N3—H3A | 120.0 |
C7—C8—H8 | 120.0 | C5—N3—H3B | 120.0 |
C8—C9—C10 | 120.41 (19) | H3A—N3—H3B | 120.0 |
C5—N1—N2—C3 | 1.27 (19) | N2—N1—C6—C11 | 123.36 (18) |
C6—N1—N2—C3 | −177.58 (15) | C11—C6—C7—C8 | −0.1 (3) |
N1—N2—C3—C4 | −1.1 (2) | N1—C6—C7—C8 | 178.04 (16) |
N2—C3—C4—C5 | 0.6 (2) | C6—C7—C8—C9 | 0.1 (3) |
N2—C3—C4—S1 | −177.98 (13) | C7—C8—C9—C10 | 0.2 (3) |
N2—N1—C5—N3 | −179.98 (15) | C8—C9—C10—C11 | −0.6 (3) |
C6—N1—C5—N3 | −1.3 (3) | C7—C6—C11—C10 | −0.3 (3) |
N2—N1—C5—C4 | −0.94 (18) | N1—C6—C11—C10 | −178.36 (17) |
C6—N1—C5—C4 | 177.78 (16) | C9—C10—C11—C6 | 0.6 (3) |
C3—C4—C5—N3 | 179.18 (18) | C5—C4—S1—O1 | 11.38 (18) |
S1—C4—C5—N3 | −2.3 (3) | C3—C4—S1—O1 | −170.40 (16) |
C3—C4—C5—N1 | 0.25 (18) | C5—C4—S1—O2 | 140.72 (15) |
S1—C4—C5—N1 | 178.78 (12) | C3—C4—S1—O2 | −41.06 (18) |
C5—N1—C6—C7 | 126.59 (18) | C5—C4—S1—C12 | −104.46 (17) |
N2—N1—C6—C7 | −54.8 (2) | C3—C4—S1—C12 | 73.77 (18) |
C5—N1—C6—C11 | −55.3 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O2i | 0.86 | 2.27 | 3.036 (2) | 148 |
N3—H3B···O1 | 0.86 | 2.38 | 2.968 (2) | 126 |
N3—H3B···N2ii | 0.86 | 2.44 | 3.234 (2) | 154 |
Symmetry codes: (i) x+1/2, −y+3/2, z−1/2; (ii) x−1/2, −y+3/2, z−1/2. |