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In the title compound, C24H21N3O4S, the salicylaldehyde group makes dihedral angles of 2.81 (15), 26.11 (13) and 55.81 (14)°, respectively, with the pyrazolone ring, the phenyl ring attached to S and the phenyl ring attached to N. The crystal packing is stabilized by weak nonclassical intra- and inter­molecular C—H...O hydrogen bonds and C—H...π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806043546/at2134sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806043546/at2134Isup2.hkl
Contains datablock I

CCDC reference: 651463

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.110
  • Data-to-parameter ratio = 7.2

checkCIF/PLATON results

No syntax errors found



Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.500 From the CIF: _refine_ls_abs_structure_Flack_su 0.200 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.16 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C1 -C6 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C19 -C24 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 8
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 2092 Count of symmetry unique reflns 1836 Completeness (_total/calc) 113.94% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 256 Fraction of Friedel pairs measured 0.139 Are heavy atom types Z>Si present yes PLAT033_ALERT_2_G Flack Parameter Value Deviates 2 * su from zero. 0.50 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

(E)-2-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4- ylimino)methylene]phenyl benzenesulfonate top
Crystal data top
C24H21N3O4SF(000) = 468
Mr = 447.51Dx = 1.432 Mg m3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 1280 reflections
a = 8.822 (7) Åθ = 2.3–23.0°
b = 10.793 (8) ŵ = 0.20 mm1
c = 11.029 (8) ÅT = 294 K
β = 98.896 (13)°Block, yellow
V = 1037.5 (14) Å30.24 × 0.20 × 0.16 mm
Z = 2
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2092 independent reflections
Radiation source: fine-focus sealed tube1621 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 106
Tmin = 0.941, Tmax = 0.969k = 1212
4141 measured reflectionsl = 1013
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0613P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.007
2092 reflectionsΔρmax = 0.23 e Å3
292 parametersΔρmin = 0.43 e Å3
2 restraintsAbsolute structure: Flack (1983), with 256 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.5 (2)
Special details top

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.97999 (19)0.21638 (11)1.21168 (15)0.0377 (3)
O10.9790 (5)0.2292 (3)1.0846 (4)0.0569 (11)
O21.1186 (4)0.1796 (3)1.2858 (4)0.0498 (10)
O30.8471 (4)0.1231 (3)1.2316 (3)0.0349 (8)
O40.5268 (5)0.2426 (3)0.8969 (4)0.0457 (10)
N10.6227 (5)0.0358 (4)0.9182 (4)0.0344 (10)
N20.3830 (5)0.0603 (4)0.6497 (4)0.0352 (10)
N30.3897 (5)0.1718 (4)0.7149 (4)0.0356 (10)
C10.9070 (6)0.3476 (4)1.2737 (5)0.0326 (12)
C20.7719 (6)0.3989 (5)1.2155 (5)0.0445 (14)
H20.71920.36351.14440.053*
C30.7171 (7)0.5027 (5)1.2647 (6)0.0503 (15)
H30.62740.53991.22620.060*
C40.7945 (7)0.5518 (5)1.3709 (6)0.0525 (16)
H40.75560.62121.40530.063*
C50.9271 (8)0.5003 (5)1.4261 (6)0.0565 (17)
H50.97960.53571.49740.068*
C60.9846 (7)0.3967 (5)1.3782 (5)0.0472 (15)
H61.07520.36061.41670.057*
C70.8741 (6)0.0036 (4)1.2073 (5)0.0310 (12)
C80.9600 (6)0.0697 (5)1.2975 (5)0.0400 (14)
H81.00120.03261.37130.048*
C90.9845 (7)0.1939 (5)1.2766 (6)0.0488 (16)
H91.04300.24181.33640.059*
C100.9215 (7)0.2458 (5)1.1664 (5)0.0466 (15)
H100.93990.32891.15160.056*
C110.8336 (6)0.1786 (5)1.0795 (5)0.0407 (13)
H110.79150.21631.00610.049*
C120.8048 (6)0.0531 (4)1.0977 (5)0.0330 (12)
C130.7053 (6)0.0182 (5)1.0053 (5)0.0354 (12)
H130.70290.10411.01100.042*
C140.5280 (6)0.0286 (4)0.8295 (5)0.0322 (12)
C150.4563 (6)0.0242 (4)0.7248 (5)0.0319 (12)
C160.4868 (6)0.1573 (5)0.8240 (5)0.0344 (12)
C170.4522 (6)0.1582 (4)0.6918 (5)0.0420 (14)
H17A0.52160.20310.75170.063*
H17B0.48220.16830.61240.063*
H17C0.35000.18950.69010.063*
C180.2493 (7)0.0396 (5)0.5589 (5)0.0477 (14)
H18A0.25960.03770.51800.072*
H18B0.23960.10570.49990.072*
H18C0.15950.03720.59820.072*
C190.3770 (6)0.2864 (5)0.6480 (5)0.0365 (12)
C200.4375 (7)0.2975 (5)0.5430 (5)0.0448 (15)
H200.48450.23050.51090.054*
C210.4276 (8)0.4120 (6)0.4845 (6)0.0566 (16)
H210.46370.42130.41020.068*
C220.3647 (8)0.5108 (6)0.5361 (7)0.0622 (18)
H220.36320.58810.49890.075*
C230.3041 (8)0.4971 (5)0.6415 (6)0.0539 (17)
H230.25910.56450.67470.065*
C240.3093 (7)0.3838 (5)0.6991 (5)0.0459 (15)
H240.26790.37350.77110.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0431 (8)0.0266 (7)0.0442 (8)0.0009 (7)0.0091 (6)0.0030 (7)
O10.089 (3)0.038 (2)0.048 (3)0.006 (2)0.027 (2)0.0044 (19)
O20.038 (2)0.035 (2)0.073 (3)0.0053 (19)0.0031 (19)0.0066 (19)
O30.036 (2)0.0218 (17)0.047 (2)0.0015 (15)0.0076 (15)0.0009 (15)
O40.061 (3)0.025 (2)0.046 (2)0.0008 (18)0.0059 (19)0.0012 (17)
N10.038 (2)0.028 (2)0.038 (3)0.002 (2)0.009 (2)0.001 (2)
N20.044 (3)0.024 (2)0.035 (2)0.002 (2)0.003 (2)0.0018 (19)
N30.045 (3)0.024 (2)0.036 (2)0.002 (2)0.001 (2)0.0014 (18)
C10.035 (3)0.024 (3)0.038 (3)0.000 (2)0.004 (2)0.001 (2)
C20.045 (3)0.031 (3)0.054 (4)0.001 (3)0.002 (3)0.001 (3)
C30.049 (4)0.039 (3)0.063 (4)0.010 (3)0.009 (3)0.008 (3)
C40.067 (4)0.026 (3)0.067 (4)0.009 (3)0.018 (3)0.003 (3)
C50.070 (5)0.036 (3)0.057 (4)0.003 (3)0.008 (3)0.013 (3)
C60.046 (3)0.034 (3)0.058 (4)0.008 (3)0.004 (3)0.000 (3)
C70.037 (3)0.019 (2)0.038 (3)0.004 (2)0.009 (2)0.000 (2)
C80.045 (3)0.038 (3)0.036 (3)0.003 (3)0.001 (3)0.002 (2)
C90.053 (4)0.034 (3)0.057 (4)0.008 (3)0.001 (3)0.011 (3)
C100.054 (4)0.024 (3)0.060 (4)0.006 (3)0.004 (3)0.001 (3)
C110.047 (3)0.028 (3)0.046 (3)0.003 (3)0.003 (3)0.007 (2)
C120.035 (3)0.024 (3)0.042 (3)0.001 (2)0.008 (2)0.001 (2)
C130.041 (3)0.023 (3)0.041 (3)0.000 (2)0.004 (2)0.003 (2)
C140.034 (3)0.027 (3)0.034 (3)0.003 (2)0.000 (2)0.003 (2)
C150.035 (3)0.023 (2)0.038 (3)0.007 (2)0.009 (2)0.001 (2)
C160.044 (3)0.025 (3)0.036 (3)0.007 (2)0.009 (3)0.001 (2)
C170.044 (4)0.026 (3)0.057 (4)0.001 (2)0.011 (3)0.007 (3)
C180.052 (3)0.037 (3)0.050 (3)0.002 (3)0.004 (3)0.004 (3)
C190.038 (3)0.030 (3)0.038 (3)0.001 (2)0.003 (2)0.006 (2)
C200.053 (4)0.041 (4)0.040 (4)0.002 (3)0.006 (3)0.004 (3)
C210.062 (4)0.059 (4)0.049 (4)0.011 (4)0.009 (3)0.011 (3)
C220.073 (5)0.037 (4)0.070 (5)0.003 (3)0.010 (4)0.019 (3)
C230.068 (5)0.027 (3)0.062 (4)0.001 (3)0.005 (4)0.001 (3)
C240.045 (3)0.035 (3)0.055 (4)0.001 (3)0.002 (3)0.005 (3)
Geometric parameters (Å, º) top
S1—O11.408 (4)C9—C101.375 (7)
S1—O21.418 (4)C9—H90.930
S1—O31.586 (4)C10—C111.348 (7)
S1—C11.739 (5)C10—H100.930
O3—C71.421 (5)C11—C121.398 (7)
O4—C161.237 (6)C11—H110.930
N1—C131.256 (6)C12—C131.457 (7)
N1—C141.373 (6)C13—H130.930
N2—C151.331 (6)C14—C151.353 (7)
N2—N31.398 (6)C14—C161.436 (7)
N2—C181.442 (7)C15—C171.490 (7)
N3—C161.374 (6)C17—H17A0.960
N3—C191.435 (6)C17—H17B0.960
C1—C61.354 (7)C17—H17C0.960
C1—C21.379 (7)C18—H18A0.960
C2—C31.365 (8)C18—H18B0.960
C2—H20.930C18—H18C0.960
C3—C41.367 (8)C19—C201.354 (8)
C3—H30.930C19—C241.373 (8)
C4—C51.352 (8)C20—C211.390 (8)
C4—H40.930C20—H200.930
C5—C61.368 (8)C21—C221.366 (10)
C5—H50.930C21—H210.930
C6—H60.930C22—C231.360 (10)
C7—C81.357 (7)C22—H220.930
C7—C121.376 (7)C23—C241.376 (8)
C8—C91.382 (8)C23—H230.930
C8—H80.930C24—H240.930
O1—S1—O2118.3 (3)C12—C11—H11119.4
O1—S1—O3108.0 (2)C7—C12—C11115.9 (4)
O2—S1—O3109.4 (2)C7—C12—C13123.1 (4)
O1—S1—C1111.5 (2)C11—C12—C13121.0 (5)
O2—S1—C1109.9 (2)N1—C13—C12120.3 (5)
O3—S1—C197.8 (2)N1—C13—H13119.8
C7—O3—S1115.8 (3)C12—C13—H13119.8
C13—N1—C14121.8 (4)C15—C14—N1123.2 (4)
C15—N2—N3107.0 (4)C15—C14—C16106.8 (4)
C15—N2—C18126.4 (4)N1—C14—C16130.0 (5)
N3—N2—C18117.1 (4)N2—C15—C14111.1 (4)
C16—N3—N2108.9 (4)N2—C15—C17121.5 (5)
C16—N3—C19122.4 (4)C14—C15—C17127.4 (5)
N2—N3—C19119.0 (4)O4—C16—N3124.2 (5)
C6—C1—C2121.7 (5)O4—C16—C14130.4 (5)
C6—C1—S1118.9 (4)N3—C16—C14105.5 (4)
C2—C1—S1119.3 (4)C15—C17—H17A109.5
C3—C2—C1118.6 (5)C15—C17—H17B109.5
C3—C2—H2120.7H17A—C17—H17B109.5
C1—C2—H2120.7C15—C17—H17C109.5
C2—C3—C4119.8 (5)H17A—C17—H17C109.5
C2—C3—H3120.1H17B—C17—H17C109.5
C4—C3—H3120.1N2—C18—H18A109.5
C5—C4—C3120.6 (5)N2—C18—H18B109.5
C5—C4—H4119.7H18A—C18—H18B109.5
C3—C4—H4119.7N2—C18—H18C109.5
C4—C5—C6120.6 (5)H18A—C18—H18C109.5
C4—C5—H5119.7H18B—C18—H18C109.5
C6—C5—H5119.7C20—C19—C24122.5 (5)
C1—C6—C5118.6 (5)C20—C19—N3120.4 (5)
C1—C6—H6120.7C24—C19—N3117.0 (5)
C5—C6—H6120.7C19—C20—C21118.1 (6)
C8—C7—C12124.2 (4)C19—C20—H20121.0
C8—C7—O3117.3 (4)C21—C20—H20121.0
C12—C7—O3118.4 (4)C22—C21—C20120.0 (6)
C7—C8—C9118.1 (5)C22—C21—H21120.0
C7—C8—H8120.9C20—C21—H21120.0
C9—C8—H8120.9C23—C22—C21120.7 (6)
C10—C9—C8119.4 (5)C23—C22—H22119.7
C10—C9—H9120.3C21—C22—H22119.7
C8—C9—H9120.3C22—C23—C24120.1 (6)
C11—C10—C9121.2 (5)C22—C23—H23120.0
C11—C10—H10119.4C24—C23—H23120.0
C9—C10—H10119.4C19—C24—C23118.5 (6)
C10—C11—C12121.1 (5)C19—C24—H24120.7
C10—C11—H11119.4C23—C24—H24120.7
O1—S1—O3—C772.8 (4)C14—N1—C13—C12179.8 (5)
O2—S1—O3—C757.2 (4)C7—C12—C13—N1166.6 (5)
C1—S1—O3—C7171.5 (3)C11—C12—C13—N112.6 (7)
C15—N2—N3—C168.6 (6)C13—N1—C14—C15169.3 (5)
C18—N2—N3—C16157.1 (5)C13—N1—C14—C169.3 (8)
C15—N2—N3—C19155.4 (4)N3—N2—C15—C148.1 (6)
C18—N2—N3—C1956.1 (6)C18—N2—C15—C14152.9 (6)
O1—S1—C1—C6133.2 (5)N3—N2—C15—C17171.0 (5)
O2—S1—C1—C60.1 (5)C18—N2—C15—C1726.3 (8)
O3—S1—C1—C6113.9 (4)N1—C14—C15—N2174.3 (5)
O1—S1—C1—C247.0 (5)C16—C14—C15—N24.6 (6)
O2—S1—C1—C2179.9 (4)N1—C14—C15—C176.6 (8)
O3—S1—C1—C265.9 (5)C16—C14—C15—C17174.5 (5)
C6—C1—C2—C30.8 (8)N2—N3—C16—O4173.5 (5)
S1—C1—C2—C3179.3 (5)C19—N3—C16—O428.0 (8)
C1—C2—C3—C41.4 (9)N2—N3—C16—C145.7 (6)
C2—C3—C4—C51.6 (9)C19—N3—C16—C14151.1 (5)
C3—C4—C5—C61.3 (10)C15—C14—C16—O4178.2 (5)
C2—C1—C6—C50.5 (9)N1—C14—C16—O40.6 (10)
S1—C1—C6—C5179.6 (5)C15—C14—C16—N30.8 (6)
C4—C5—C6—C10.7 (10)N1—C14—C16—N3179.6 (5)
S1—O3—C7—C882.5 (5)C16—N3—C19—C20107.0 (6)
S1—O3—C7—C12101.4 (5)N2—N3—C19—C2035.1 (7)
C12—C7—C8—C92.6 (8)C16—N3—C19—C2469.4 (7)
O3—C7—C8—C9178.5 (5)N2—N3—C19—C24148.4 (5)
C7—C8—C9—C100.2 (9)C24—C19—C20—C211.2 (9)
C8—C9—C10—C111.4 (9)N3—C19—C20—C21177.4 (5)
C9—C10—C11—C120.7 (9)C19—C20—C21—C223.1 (9)
C8—C7—C12—C113.2 (8)C20—C21—C22—C233.4 (10)
O3—C7—C12—C11179.1 (4)C21—C22—C23—C241.7 (10)
C8—C7—C12—C13176.1 (5)C20—C19—C24—C230.5 (8)
O3—C7—C12—C130.2 (7)N3—C19—C24—C23175.9 (5)
C10—C11—C12—C71.5 (8)C22—C23—C24—C190.2 (9)
C10—C11—C12—C13177.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C13—H13···O40.932.373.032 (6)128
C4—H4···O4i0.932.493.286 (7)144
C17—H17C···O2ii0.962.443.276 (7)145
C3—H3···Cgi0.932.603.516 (2)168
Symmetry codes: (i) x, y+1, z+1/2; (ii) x1, y, z1/2.
 

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