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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805033556/ac6208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805033556/ac6208Isup2.hkl
Contains datablock I

CCDC reference: 289623

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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
C10H11N3O2SF(000) = 496
Mr = 237.28Dx = 1.445 Mg m3
Monoclinic, P21/nMelting point: 407 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.083 (2) ÅCell parameters from 20 reflections
b = 12.274 (3) Åθ = 7–20°
c = 11.040 (3) ŵ = 0.29 mm1
β = 95.20 (3)°T = 293 K
V = 1090.8 (5) Å3Prism, colourless
Z = 40.30 × 0.20 × 0.15 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.039
Radiation source: fine-focus sealed tubeθmax = 27.5°, θmin = 2.5°
Graphite monochromatorh = 110
ω/2θ scansk = 115
3298 measured reflectionsl = 1414
2504 independent reflections3 standard reflections every 97 reflections
2080 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-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 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.58298 (17)0.67943 (12)0.44428 (12)0.0327 (3)
N20.60842 (18)0.70948 (13)0.56571 (13)0.0393 (3)
C30.4813 (2)0.77146 (15)0.58330 (15)0.0375 (4)
H30.46400.80290.65780.045*
C40.37345 (19)0.78532 (13)0.47696 (14)0.0309 (3)
C50.44344 (19)0.72442 (13)0.38750 (14)0.0293 (3)
C60.6987 (2)0.60653 (14)0.39555 (14)0.0332 (3)
C70.8652 (2)0.63415 (15)0.40759 (17)0.0412 (4)
H70.90000.69950.44420.049*
C80.9792 (3)0.56350 (18)0.3646 (2)0.0515 (5)
H81.09160.58110.37230.062*
C90.9269 (3)0.46736 (18)0.3106 (2)0.0559 (5)
H91.00410.41990.28190.067*
C100.7608 (3)0.44073 (17)0.2984 (2)0.0559 (5)
H100.72680.37560.26100.067*
C110.6437 (2)0.50997 (16)0.34145 (18)0.0455 (4)
H110.53150.49190.33410.055*
S10.19650 (5)0.86328 (3)0.46018 (4)0.03279 (14)
O10.11200 (17)0.83895 (13)0.34374 (12)0.0520 (4)
O20.10668 (17)0.85023 (12)0.56575 (12)0.0494 (4)
C120.2621 (3)1.00009 (16)0.4589 (2)0.0505 (5)
H12A0.32411.01220.39000.076*
H12B0.33111.01550.53230.076*
H12C0.16681.04710.45370.076*
N30.39312 (18)0.70690 (13)0.26915 (13)0.0404 (4)
H3A0.45040.66550.22600.048*
H3B0.30380.73710.23690.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0318 (7)0.0383 (7)0.0277 (6)0.0024 (6)0.0012 (5)0.0022 (6)
N20.0397 (8)0.0494 (9)0.0278 (7)0.0026 (7)0.0029 (6)0.0029 (6)
C30.0407 (9)0.0444 (9)0.0273 (8)0.0005 (7)0.0020 (6)0.0047 (7)
C40.0303 (8)0.0353 (8)0.0275 (7)0.0013 (6)0.0038 (6)0.0018 (6)
C50.0280 (7)0.0322 (8)0.0279 (7)0.0035 (6)0.0029 (5)0.0008 (6)
C60.0349 (8)0.0335 (8)0.0311 (8)0.0033 (6)0.0030 (6)0.0029 (6)
C70.0377 (9)0.0427 (9)0.0434 (9)0.0010 (8)0.0049 (7)0.0025 (8)
C80.0398 (10)0.0601 (13)0.0561 (12)0.0114 (9)0.0127 (8)0.0119 (10)
C90.0664 (14)0.0496 (11)0.0546 (12)0.0221 (10)0.0212 (10)0.0071 (10)
C100.0733 (15)0.0378 (10)0.0577 (12)0.0075 (10)0.0123 (11)0.0065 (9)
C110.0463 (10)0.0393 (10)0.0509 (11)0.0003 (8)0.0042 (8)0.0036 (8)
S10.0264 (2)0.0411 (2)0.0316 (2)0.00034 (16)0.00733 (14)0.00084 (16)
O10.0391 (7)0.0732 (10)0.0421 (7)0.0080 (7)0.0054 (6)0.0076 (7)
O20.0426 (7)0.0634 (9)0.0455 (8)0.0007 (6)0.0223 (6)0.0021 (6)
C120.0449 (11)0.0391 (10)0.0690 (14)0.0039 (8)0.0143 (9)0.0054 (9)
N30.0385 (8)0.0544 (9)0.0276 (7)0.0108 (7)0.0009 (5)0.0067 (6)
Geometric parameters (Å, º) top
N1—C51.357 (2)C8—H80.9300
N1—N21.388 (2)C9—C101.376 (3)
N1—C61.434 (2)C9—H90.9300
N2—C31.307 (2)C10—C111.388 (3)
C3—C41.408 (2)C10—H100.9300
C3—H30.9300C11—H110.9300
C4—C51.398 (2)S1—O11.4314 (14)
C4—S11.717 (2)S1—O21.4368 (14)
C5—N31.350 (2)S1—C121.761 (2)
C6—C71.383 (2)C12—H12A0.9600
C6—C111.382 (3)C12—H12B0.9600
C7—C81.380 (3)C12—H12C0.9600
C7—H70.9300N3—H3A0.8600
C8—C91.372 (3)N3—H3B0.8600
C5—N1—N2112.47 (13)C8—C9—H9119.8
C5—N1—C6128.59 (14)C10—C9—H9119.8
N2—N1—C6118.93 (13)C9—C10—C11120.7 (2)
C3—N2—N1104.39 (13)C9—C10—H10119.6
N2—C3—C4112.46 (15)C11—C10—H10119.6
N2—C3—H3123.8C6—C11—C10118.04 (19)
C4—C3—H3123.8C6—C11—H11121.0
C5—C4—C3105.36 (14)C10—C11—H11121.0
C5—C4—S1127.45 (12)O1—S1—O2118.04 (9)
C3—C4—S1127.17 (13)O1—S1—C4107.80 (8)
N3—C5—N1123.17 (15)O2—S1—C4109.12 (8)
N3—C5—C4131.53 (15)O1—S1—C12108.13 (11)
N1—C5—C4105.29 (14)O2—S1—C12106.70 (10)
C7—C6—C11121.60 (17)C4—S1—C12106.48 (9)
C7—C6—N1118.25 (16)S1—C12—H12A109.5
C11—C6—N1120.11 (16)S1—C12—H12B109.5
C8—C7—C6119.16 (18)H12A—C12—H12B109.5
C8—C7—H7120.4S1—C12—H12C109.5
C6—C7—H7120.4H12A—C12—H12C109.5
C9—C8—C7120.1 (2)H12B—C12—H12C109.5
C9—C8—H8120.0C5—N3—H3A120.0
C7—C8—H8120.0C5—N3—H3B120.0
C8—C9—C10120.41 (19)H3A—N3—H3B120.0
C5—N1—N2—C31.27 (19)N2—N1—C6—C11123.36 (18)
C6—N1—N2—C3177.58 (15)C11—C6—C7—C80.1 (3)
N1—N2—C3—C41.1 (2)N1—C6—C7—C8178.04 (16)
N2—C3—C4—C50.6 (2)C6—C7—C8—C90.1 (3)
N2—C3—C4—S1177.98 (13)C7—C8—C9—C100.2 (3)
N2—N1—C5—N3179.98 (15)C8—C9—C10—C110.6 (3)
C6—N1—C5—N31.3 (3)C7—C6—C11—C100.3 (3)
N2—N1—C5—C40.94 (18)N1—C6—C11—C10178.36 (17)
C6—N1—C5—C4177.78 (16)C9—C10—C11—C60.6 (3)
C3—C4—C5—N3179.18 (18)C5—C4—S1—O111.38 (18)
S1—C4—C5—N32.3 (3)C3—C4—S1—O1170.40 (16)
C3—C4—C5—N10.25 (18)C5—C4—S1—O2140.72 (15)
S1—C4—C5—N1178.78 (12)C3—C4—S1—O241.06 (18)
C5—N1—C6—C7126.59 (18)C5—C4—S1—C12104.46 (17)
N2—N1—C6—C754.8 (2)C3—C4—S1—C1273.77 (18)
C5—N1—C6—C1155.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O2i0.862.273.036 (2)148
N3—H3B···O10.862.382.968 (2)126
N3—H3B···N2ii0.862.443.234 (2)154
Symmetry codes: (i) x+1/2, y+3/2, z1/2; (ii) x1/2, y+3/2, z1/2.
 

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