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The title compound, C15H14NO2S, was prepared by the esterification of benzhydryl­thio­acetic acid, followed by amidation and oxidation. There are two independent molecules in the asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001382/ob6340sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001382/ob6340Isup2.hkl
Contains datablock I

CCDC reference: 236078

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.115
  • Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for C12 - C13 = 6.24 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); software used to prepare material for publication: CrystalStructure.

2-(Benzhydrylsulfinyl)acetamide top
Crystal data top
C15H15NO2SF(000) = 1152.00
Mr = 273.35Dx = 1.311 Mg m3
Monoclinic, P21/nMelting point: 164 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.7107 Å
a = 20.961 (1) ÅCell parameters from 16675 reflections
b = 9.7061 (5) Åθ = 2.3–27.4°
c = 20.894 (1) ŵ = 0.23 mm1
β = 139.336 (1)°T = 298 K
V = 2770.0 (3) Å3Prism, colorless
Z = 80.29 × 0.28 × 0.20 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3764 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.027
ω scansθmax = 27.4°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 2727
Tmin = 0.842, Tmax = 0.955k = 1212
47104 measured reflectionsl = 2727
6218 independent reflections
Refinement top
Refinement on F2H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.042 w = (4Fo2)/[0.002Fo2 + 1.6σ(Fo2)]
wR(F2) = 0.115(Δ/σ)max < 0.001
S = 1.00Δρmax = 0.41 e Å3
3776 reflectionsΔρmin = 0.30 e Å3
373 parameters
Special details top

Refinement. Refinement using reflections with F2 > 2.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.17543 (4)0.51139 (5)0.26933 (4)0.0391 (1)
S20.26337 (4)0.52331 (5)0.67238 (4)0.0406 (2)
O10.3851 (1)0.5149 (2)0.4503 (1)0.0719 (6)
O20.1909 (1)0.6061 (2)0.2262 (1)0.0556 (5)
O30.4415 (1)0.5320 (2)0.8805 (1)0.0656 (5)
O40.2191 (1)0.6187 (2)0.6863 (1)0.0612 (5)
N10.4209 (1)0.3495 (2)0.4060 (2)0.0544 (6)
H2010.48770.37620.45410.059*
H2020.39760.27390.36370.059*
N20.4097 (1)0.3539 (2)0.9222 (1)0.0530 (6)
H4010.46030.37820.98980.059*
H4020.37020.27520.90020.058*
C10.2556 (1)0.3668 (2)0.3188 (2)0.0432 (6)
H1010.24090.32300.26810.047*
H1020.24720.30290.34650.047*
C20.3606 (2)0.4176 (2)0.3978 (2)0.0435 (6)
C30.0605 (1)0.4197 (2)0.1651 (2)0.0393 (6)
H30.06690.37610.12950.045*
C40.0216 (2)0.5235 (2)0.0975 (2)0.0410 (6)
C50.0918 (2)0.5029 (3)0.0033 (2)0.0579 (8)
H50.08560.42660.02670.071*
C60.1693 (2)0.5940 (4)0.0681 (2)0.080 (1)
H60.21800.57860.13680.092*
C70.1771 (2)0.7047 (4)0.0350 (3)0.084 (1)
H70.23000.76740.08020.091*
C80.1087 (2)0.7266 (3)0.0635 (3)0.073 (1)
H80.11460.80390.08660.082*
C90.0310 (2)0.6363 (2)0.1301 (2)0.0536 (7)
H90.01650.65110.19870.058*
C100.0449 (1)0.3070 (2)0.2024 (1)0.0374 (5)
C110.0478 (2)0.1708 (3)0.1859 (2)0.0568 (8)
H110.05890.14950.15070.069*
C120.0338 (2)0.0669 (3)0.2201 (3)0.076 (1)
H120.03520.02670.20790.086*
C130.0174 (2)0.0980 (3)0.2705 (2)0.0669 (8)
H130.00840.02670.29430.073*
C140.0157 (2)0.2329 (3)0.2878 (2)0.0565 (7)
H140.00420.25500.32280.064*
C150.0287 (2)0.3363 (3)0.2543 (2)0.0454 (6)
H150.02700.42970.26650.051*
C160.3115 (2)0.3807 (2)0.7532 (1)0.0425 (6)
H3010.33590.31340.74290.047*
H3020.26110.34130.74030.047*
C170.3941 (2)0.4298 (2)0.8588 (2)0.0414 (6)
C180.1595 (2)0.4303 (2)0.5580 (1)0.0376 (5)
H180.12130.39410.56310.044*
C190.0957 (2)0.5312 (2)0.4727 (2)0.0416 (6)
C200.0050 (2)0.5143 (3)0.3987 (2)0.0586 (8)
H200.03180.44360.40440.069*
C210.0657 (2)0.6017 (4)0.3174 (2)0.082 (1)
H210.13470.58940.26600.088*
C220.0261 (3)0.7044 (4)0.3107 (3)0.084 (1)
H220.06780.76420.25540.096*
C230.0713 (3)0.7220 (3)0.3823 (2)0.077 (1)
H230.09770.79340.37650.089*
C240.1331 (2)0.6359 (3)0.4636 (2)0.0592 (8)
H240.20200.64870.51400.066*
C250.1956 (1)0.3097 (2)0.5462 (1)0.0360 (5)
C260.1765 (2)0.1771 (2)0.5525 (2)0.0477 (7)
H260.14060.16360.56370.058*
C270.2104 (2)0.0656 (3)0.5435 (2)0.0639 (8)
H270.19660.02560.54700.070*
C280.2625 (2)0.0856 (3)0.5279 (2)0.0654 (9)
H280.28590.00900.52200.074*
C290.2821 (2)0.2167 (3)0.5224 (2)0.0587 (8)
H290.31880.23010.51210.070*
C300.2485 (2)0.3282 (3)0.5306 (2)0.0467 (6)
H300.26190.41890.52630.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0332 (3)0.0326 (3)0.0422 (3)0.0021 (2)0.0260 (3)0.0017 (2)
S20.0455 (3)0.0324 (3)0.0343 (3)0.0001 (2)0.0275 (3)0.0017 (2)
O10.0382 (9)0.070 (1)0.072 (1)0.0054 (9)0.032 (1)0.034 (1)
O20.0449 (9)0.0446 (9)0.066 (1)0.0024 (8)0.0386 (9)0.0128 (8)
O30.069 (1)0.061 (1)0.0389 (9)0.031 (1)0.033 (1)0.0096 (8)
O40.075 (1)0.046 (1)0.048 (1)0.0180 (9)0.042 (1)0.0012 (8)
N10.037 (1)0.050 (1)0.061 (1)0.0050 (9)0.033 (1)0.019 (1)
N20.060 (1)0.050 (1)0.036 (1)0.019 (1)0.033 (1)0.0076 (9)
C10.037 (1)0.033 (1)0.048 (1)0.0009 (9)0.029 (1)0.000 (1)
C20.035 (1)0.038 (1)0.043 (1)0.000 (1)0.025 (1)0.004 (1)
C30.036 (1)0.040 (1)0.037 (1)0.005 (1)0.026 (1)0.005 (1)
C40.033 (1)0.044 (1)0.042 (1)0.0030 (9)0.027 (1)0.008 (1)
C50.044 (1)0.087 (2)0.046 (1)0.002 (1)0.035 (1)0.009 (1)
C60.046 (2)0.133 (3)0.050 (2)0.009 (2)0.033 (1)0.037 (2)
C70.050 (2)0.086 (2)0.092 (3)0.020 (2)0.047 (2)0.058 (2)
C80.054 (2)0.043 (1)0.109 (3)0.007 (1)0.058 (2)0.018 (2)
C90.041 (1)0.043 (1)0.059 (2)0.001 (1)0.033 (1)0.003 (1)
C100.030 (1)0.034 (1)0.036 (1)0.0036 (9)0.021 (1)0.0007 (9)
C110.061 (2)0.041 (1)0.071 (2)0.010 (1)0.050 (2)0.011 (1)
C120.082 (2)0.031 (1)0.102 (2)0.006 (1)0.066 (2)0.001 (1)
C130.057 (2)0.057 (2)0.068 (2)0.004 (1)0.043 (2)0.017 (1)
C140.049 (1)0.068 (2)0.044 (1)0.008 (1)0.033 (1)0.004 (1)
C150.041 (1)0.044 (1)0.044 (1)0.005 (1)0.030 (1)0.003 (1)
C160.046 (1)0.034 (1)0.036 (1)0.001 (1)0.028 (1)0.001 (1)
C170.042 (1)0.037 (1)0.035 (1)0.004 (1)0.026 (1)0.003 (1)
C180.037 (1)0.037 (1)0.035 (1)0.000 (1)0.026 (1)0.003 (1)
C190.044 (1)0.040 (1)0.036 (1)0.009 (1)0.029 (1)0.001 (1)
C200.048 (1)0.077 (2)0.047 (1)0.013 (1)0.035 (1)0.001 (1)
C210.048 (2)0.123 (3)0.047 (2)0.035 (2)0.029 (1)0.006 (2)
C220.099 (3)0.084 (2)0.058 (2)0.052 (2)0.057 (2)0.027 (2)
C230.104 (3)0.055 (2)0.062 (2)0.023 (2)0.061 (2)0.018 (1)
C240.066 (2)0.047 (1)0.050 (1)0.007 (1)0.040 (1)0.006 (1)
C250.033 (1)0.038 (1)0.028 (1)0.0028 (9)0.021 (1)0.0019 (9)
C260.054 (1)0.041 (1)0.050 (1)0.000 (1)0.040 (1)0.005 (1)
C270.071 (2)0.038 (1)0.065 (2)0.004 (1)0.047 (2)0.005 (1)
C280.063 (2)0.062 (2)0.060 (2)0.021 (1)0.044 (2)0.004 (1)
C290.045 (1)0.083 (2)0.048 (1)0.014 (1)0.035 (1)0.001 (1)
C300.042 (1)0.052 (1)0.042 (1)0.004 (1)0.031 (1)0.001 (1)
Geometric parameters (Å, º) top
S1—O21.485 (3)C12—C131.368 (9)
S1—C11.797 (2)C12—H120.950
S1—C31.838 (2)C13—C141.366 (5)
S2—O41.487 (3)C13—H130.950
S2—C161.789 (2)C14—C151.365 (5)
S2—C181.837 (2)C14—H140.950
O1—C21.226 (4)C15—H150.950
O3—C171.222 (3)C16—C171.515 (3)
N1—C21.317 (5)C16—H3010.950
N1—H2010.950C16—H3020.950
N1—H2020.950C18—C191.520 (3)
N2—C171.322 (5)C18—C251.513 (4)
N2—H4010.950C18—H180.950
N2—H4020.950C19—C201.386 (4)
C1—C21.517 (3)C19—C241.383 (5)
C1—H1010.950C20—C211.394 (4)
C1—H1020.950C20—H200.950
C3—C41.512 (3)C21—C221.371 (8)
C3—C101.515 (5)C21—H210.950
C3—H30.950C22—C231.343 (6)
C4—C51.394 (4)C22—H220.950
C4—C91.379 (5)C23—C241.386 (4)
C5—C61.384 (4)C23—H230.950
C5—H50.950C24—H240.950
C6—C71.353 (7)C25—C261.384 (4)
C6—H60.950C25—C301.383 (6)
C7—C81.364 (6)C26—C271.384 (6)
C7—H70.950C26—H260.950
C8—C91.385 (3)C27—C281.370 (8)
C8—H80.950C27—H270.950
C9—H90.950C28—C291.369 (5)
C10—C111.379 (4)C28—H280.950
C10—C151.390 (6)C29—C301.372 (5)
C11—C121.388 (7)C29—H290.950
C11—H110.950C30—H300.950
O2—S1—C1107.1 (2)C15—C14—H14119.6
O2—S1—C3105.9 (1)C15—C14—C13120.9 (5)
C1—S1—C396.7 (1)H14—C14—C13119.5
O4—S2—C16106.6 (2)H15—C15—C10119.1
O4—S2—C18105.1 (1)H15—C15—C14120.1
C16—S2—C1896.4 (1)C10—C15—C14120.9 (3)
C2—N1—H201120.0C17—C16—H301109.2
C2—N1—H202120.0C17—C16—H302109.7
H201—N1—H202120.0C17—C16—S2109.5 (1)
C17—N2—H401120.0H301—C16—H302109.5
C17—N2—H402120.0H301—C16—S2109.4
H401—N2—H402120.0H302—C16—S2109.5
C2—C1—H101109.6O3—C17—N2124.5 (2)
C2—C1—H102109.6O3—C17—C16120.4 (3)
C2—C1—S1108.9 (2)N2—C17—C16115.1 (2)
H101—C1—H102109.5C19—C18—C25114.2 (3)
H101—C1—S1109.7C19—C18—H18107.6
H102—C1—S1109.6C19—C18—S2109.2 (1)
O1—C2—N1124.1 (2)C25—C18—H18107.5
O1—C2—C1120.1 (3)C25—C18—S2110.3 (2)
N1—C2—C1115.8 (2)H18—C18—S2107.8
C4—C3—C10115.1 (3)C20—C19—C24118.4 (2)
C4—C3—H3107.6C20—C19—C18118.2 (3)
C4—C3—S1108.9 (1)C24—C19—C18123.3 (2)
C10—C3—H3107.2C21—C20—H20120.8
C10—C3—S1109.9 (2)C21—C20—C19119.8 (4)
H3—C3—S1107.8H20—C20—C19119.4
C5—C4—C9118.5 (2)C22—C21—H21119.7
C5—C4—C3117.7 (3)C22—C21—C20120.2 (3)
C9—C4—C3123.8 (2)H21—C21—C20120.1
C6—C5—H5120.9C23—C22—H22119.8
C6—C5—C4119.8 (4)C23—C22—C21120.4 (3)
H5—C5—C4119.4H22—C22—C21119.8
C7—C6—H6119.3C24—C23—H23120.2
C7—C6—C5121.0 (3)C24—C23—C22120.4 (5)
H6—C6—C5119.7H23—C23—C22119.4
C8—C7—H7119.9H24—C24—C19119.1
C8—C7—C6119.9 (3)H24—C24—C23120.1
H7—C7—C6120.2C19—C24—C23120.8 (3)
C9—C8—H8119.8C26—C25—C30119.0 (3)
C9—C8—C7120.4 (4)C26—C25—C18119.1 (4)
H8—C8—C7119.8C30—C25—C18121.9 (2)
H9—C9—C4119.1C27—C26—H26120.6
H9—C9—C8120.5C27—C26—C25119.9 (4)
C4—C9—C8120.4 (3)H26—C26—C25119.5
C11—C10—C15118.2 (3)C28—C27—H27119.5
C11—C10—C3119.8 (4)C28—C27—C26120.4 (3)
C15—C10—C3122.0 (2)H27—C27—C26120.1
C12—C11—H11120.8C29—C28—H28119.8
C12—C11—C10120.2 (5)C29—C28—C27119.8 (4)
H11—C11—C10119.0H28—C28—C27120.4
C13—C12—H12119.6C30—C29—H29120.1
C13—C12—C11120.7 (3)C30—C29—C28120.4 (5)
H12—C12—C11119.7H29—C29—C28119.5
C14—C13—H13120.4H30—C30—C25119.4
C14—C13—C12119.2 (4)H30—C30—C29120.1
H13—C13—C12120.4C25—C30—C29120.5 (3)
O2—S1—C1—C260.8 (3)O4—S2—C16—C1765.0 (3)
C3—S1—C1—C2169.8 (3)C18—S2—C16—C17172.8 (3)
O2—S1—C3—C460.3 (3)O4—S2—C18—C1965.3 (3)
O2—S1—C3—C10172.7 (2)O4—S2—C18—C25168.4 (2)
C1—S1—C3—C4170.3 (3)C16—S2—C18—C19174.4 (3)
C1—S1—C3—C1062.8 (2)C16—S2—C18—C2559.3 (2)
 

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