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The title compound, C13H19NO2S, is a new potent herbicide. X-ray analysis reveals the cyclo­hexane ring to be disordered, which results in the two conformers, both of which adopt a chair conformation. An N—H...O=S hydrogen bond [2.915 (4) Å] and its centrosymmetric equivalent connect two molecules into a dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017077/kp2017sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017077/kp2017Isup2.hkl
Contains datablock I

CCDC reference: 610827

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • Disorder in main residue
  • R factor = 0.054
  • wR factor = 0.166
  • Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 26.00 Perc.
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT352_ALERT_3_C Short N-H Bond (0.87A) N1 - H1A ... 0.76 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C4 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 8.30 Deg. C8' -N1 -C8 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 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 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

N-cyclohexyl-4-methylbenzenesulfonamide top
Crystal data top
C13H19NO2SF(000) = 544
Mr = 253.35Dx = 1.224 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.812 (5) ÅCell parameters from 1331 reflections
b = 12.927 (7) Åθ = 2.5–21.3°
c = 11.095 (6) ŵ = 0.23 mm1
β = 102.294 (9)°T = 293 K
V = 1375.1 (13) Å3Prism, colourless
Z = 40.30 × 0.26 × 0.22 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2428 independent reflections
Radiation source: fine-focus sealed tube1396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
φ and ω scansθmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1990)
h = 1110
Tmin = 0.935, Tmax = 0.952k = 1215
6797 measured reflectionsl = 1313
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0804P)2 + 0.4445P]
where P = (Fo2 + 2Fc2)/3
2428 reflections(Δ/σ)max = 0.001
178 parametersΔρmax = 0.35 e Å3
62 restraintsΔρmin = 0.27 e Å3
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 > 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.56784 (10)0.11653 (7)0.37310 (8)0.0556 (4)
O10.4690 (3)0.03291 (19)0.3432 (2)0.0633 (7)
O20.6416 (3)0.1508 (2)0.2827 (2)0.0710 (8)
N10.6809 (3)0.0768 (3)0.4911 (3)0.0583 (9)
H1A0.645 (4)0.053 (3)0.539 (3)0.061 (13)*
C10.4017 (4)0.2108 (3)0.5092 (3)0.0584 (10)
H10.40030.14690.54760.070*
C20.3308 (4)0.2926 (3)0.5440 (3)0.0637 (11)
H20.28260.28380.60690.076*
C30.3290 (4)0.3884 (3)0.4879 (4)0.0623 (10)
C40.2497 (4)0.4777 (3)0.5275 (4)0.0907 (14)
H4A0.15280.46000.51550.136*
H4B0.25990.53770.47920.136*
H4C0.28610.49230.61320.136*
C50.4019 (4)0.3992 (3)0.3958 (4)0.0684 (11)
H50.40140.46270.35640.082*
C60.4761 (4)0.3180 (3)0.3601 (3)0.0611 (10)
H60.52590.32750.29840.073*
C70.4760 (3)0.2229 (3)0.4164 (3)0.0498 (9)
C80.8152 (5)0.1279 (4)0.5377 (5)0.0725 (13)0.852 (4)
H8A0.86030.14220.46870.087*0.852 (4)
C90.8013 (5)0.2257 (4)0.6039 (6)0.0895 (18)0.852 (4)
H9A0.75630.21160.67200.107*0.852 (4)
H9B0.74250.27330.54820.107*0.852 (4)
C100.9438 (5)0.2763 (4)0.6536 (6)0.104 (2)0.852 (4)
H10A0.98610.29520.58520.125*0.852 (4)
H10B0.93140.33890.69830.125*0.852 (4)
C111.0398 (5)0.2016 (4)0.7393 (5)0.0961 (19)0.852 (4)
H11A1.13200.23210.76260.115*0.852 (4)
H11B1.00450.19200.81380.115*0.852 (4)
C121.0508 (5)0.0997 (4)0.6816 (6)0.110 (2)0.852 (4)
H12A1.10380.05320.74260.132*0.852 (4)
H12B1.10120.10760.61580.132*0.852 (4)
C130.9075 (5)0.0520 (4)0.6290 (5)0.0946 (18)0.852 (4)
H13A0.86160.03580.69590.114*0.852 (4)
H13B0.91920.01190.58650.114*0.852 (4)
C8'0.815 (2)0.120 (2)0.554 (2)0.0725 (13)0.148 (4)
H8'A0.88630.07450.53350.087*0.148 (4)
C9'0.850 (2)0.227 (2)0.5161 (19)0.0895 (18)0.148 (4)
H9'A0.77900.27550.52880.107*0.148 (4)
H9'B0.85170.22720.42890.107*0.148 (4)
C10'0.992 (2)0.263 (2)0.590 (2)0.104 (2)0.148 (4)
H10C1.01250.33170.56480.125*0.148 (4)
H10D1.06450.21640.57520.125*0.148 (4)
C11'0.989 (3)0.262 (2)0.728 (2)0.0961 (19)0.148 (4)
H11C1.07760.28620.77540.115*0.148 (4)
H11D0.91670.30910.74230.115*0.148 (4)
C12'0.960 (3)0.154 (2)0.7681 (19)0.110 (2)0.148 (4)
H12C1.03780.10980.76260.132*0.148 (4)
H12D0.95180.15620.85370.132*0.148 (4)
C13'0.829 (2)0.109 (2)0.691 (2)0.0946 (18)0.148 (4)
H13C0.74930.14230.71440.114*0.148 (4)
H13D0.82520.03620.71110.114*0.148 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0663 (6)0.0551 (6)0.0461 (5)0.0102 (5)0.0140 (4)0.0000 (5)
O10.0765 (16)0.0575 (16)0.0555 (15)0.0244 (14)0.0132 (12)0.0073 (12)
O20.0863 (19)0.0781 (19)0.0539 (15)0.0150 (15)0.0270 (14)0.0042 (13)
N10.058 (2)0.058 (2)0.060 (2)0.0071 (16)0.0152 (18)0.0075 (17)
C10.065 (2)0.052 (2)0.057 (2)0.005 (2)0.0123 (19)0.0092 (18)
C20.063 (2)0.065 (3)0.064 (2)0.004 (2)0.016 (2)0.003 (2)
C30.057 (2)0.051 (2)0.069 (3)0.006 (2)0.009 (2)0.003 (2)
C40.084 (3)0.065 (3)0.114 (4)0.012 (3)0.001 (3)0.009 (3)
C50.078 (3)0.047 (2)0.072 (3)0.011 (2)0.005 (2)0.015 (2)
C60.068 (2)0.058 (2)0.053 (2)0.016 (2)0.0032 (19)0.0098 (19)
C70.049 (2)0.052 (2)0.0431 (19)0.0110 (17)0.0018 (16)0.0055 (16)
C80.074 (3)0.072 (3)0.068 (3)0.012 (2)0.007 (2)0.016 (2)
C90.069 (3)0.083 (4)0.108 (4)0.016 (3)0.000 (3)0.022 (3)
C100.077 (4)0.096 (4)0.120 (5)0.004 (3)0.024 (3)0.042 (3)
C110.082 (4)0.098 (5)0.094 (4)0.002 (3)0.012 (3)0.011 (4)
C120.076 (4)0.114 (5)0.125 (5)0.009 (3)0.013 (3)0.014 (4)
C130.083 (4)0.073 (4)0.114 (4)0.008 (3)0.009 (3)0.015 (3)
C8'0.074 (3)0.072 (3)0.068 (3)0.012 (2)0.007 (2)0.016 (2)
C9'0.069 (3)0.083 (4)0.108 (4)0.016 (3)0.000 (3)0.022 (3)
C10'0.077 (4)0.096 (4)0.120 (5)0.004 (3)0.024 (3)0.042 (3)
C11'0.082 (4)0.098 (5)0.094 (4)0.002 (3)0.012 (3)0.011 (4)
C12'0.076 (4)0.114 (5)0.125 (5)0.009 (3)0.013 (3)0.014 (4)
C13'0.083 (4)0.073 (4)0.114 (4)0.008 (3)0.009 (3)0.015 (3)
Geometric parameters (Å, º) top
S1—O21.427 (2)C10—H10A0.9700
S1—O11.443 (2)C10—H10B0.9700
S1—N11.609 (3)C11—C121.479 (6)
S1—C71.766 (4)C11—H11A0.9700
N1—C8'1.466 (10)C11—H11B0.9700
N1—C81.466 (5)C12—C131.533 (6)
N1—H1A0.76 (3)C12—H12A0.9700
C1—C21.367 (5)C12—H12B0.9700
C1—C71.391 (5)C13—H13A0.9700
C1—H10.9300C13—H13B0.9700
C2—C31.385 (5)C8'—C13'1.504 (10)
C2—H20.9300C8'—C9'1.510 (10)
C3—C51.374 (5)C8'—H8'A0.9800
C3—C41.509 (5)C9'—C10'1.527 (10)
C4—H4A0.9600C9'—H9'A0.9700
C4—H4B0.9600C9'—H9'B0.9700
C4—H4C0.9600C10'—C11'1.533 (10)
C5—C61.382 (5)C10'—H10C0.9700
C5—H50.9300C10'—H10D0.9700
C6—C71.380 (5)C11'—C12'1.513 (10)
C6—H60.9300C11'—H11C0.9700
C8—C91.484 (6)C11'—H11D0.9700
C8—C131.554 (6)C12'—C13'1.500 (10)
C8—H8A0.9800C12'—H12C0.9700
C9—C101.536 (5)C12'—H12D0.9700
C9—H9A0.9700C13'—H13C0.9700
C9—H9B0.9700C13'—H13D0.9700
C10—C111.530 (6)
O2—S1—O1119.19 (15)C12—C11—C10112.6 (4)
O2—S1—N1107.80 (18)C12—C11—H11A109.1
O1—S1—N1105.12 (16)C10—C11—H11A109.1
O2—S1—C7108.34 (17)C12—C11—H11B109.1
O1—S1—C7106.79 (16)C10—C11—H11B109.1
N1—S1—C7109.31 (17)H11A—C11—H11B107.8
C8'—N1—C88.3 (12)C11—C12—C13112.2 (4)
C8'—N1—S1131.4 (11)C11—C12—H12A109.2
C8—N1—S1123.7 (3)C13—C12—H12A109.2
C8'—N1—H1A109 (3)C11—C12—H12B109.2
C8—N1—H1A117 (3)C13—C12—H12B109.2
S1—N1—H1A111 (3)H12A—C12—H12B107.9
C2—C1—C7120.0 (3)C12—C13—C8110.8 (4)
C2—C1—H1120.0C12—C13—H13A109.5
C7—C1—H1120.0C8—C13—H13A109.5
C1—C2—C3121.6 (4)C12—C13—H13B109.5
C1—C2—H2119.2C8—C13—H13B109.5
C3—C2—H2119.2H13A—C13—H13B108.1
C5—C3—C2117.8 (4)N1—C8'—C13'109.1 (17)
C5—C3—C4121.5 (4)N1—C8'—C9'116.9 (18)
C2—C3—C4120.7 (4)C13'—C8'—C9'113.3 (10)
C3—C4—H4A109.5N1—C8'—H8'A105.6
C3—C4—H4B109.5C13'—C8'—H8'A105.5
H4A—C4—H4B109.5C9'—C8'—H8'A105.6
C3—C4—H4C109.5C8'—C9'—C10'111.1 (9)
H4A—C4—H4C109.5C8'—C9'—H9'A109.4
H4B—C4—H4C109.5C10'—C9'—H9'A109.4
C3—C5—C6121.8 (4)C8'—C9'—H9'B109.4
C3—C5—H5119.1C10'—C9'—H9'B109.4
C6—C5—H5119.1H9'A—C9'—H9'B108.0
C7—C6—C5119.7 (4)C9'—C10'—C11'108.9 (10)
C7—C6—H6120.2C9'—C10'—H10C109.9
C5—C6—H6120.2C11'—C10'—H10C109.9
C6—C7—C1119.2 (4)C9'—C10'—H10D109.9
C6—C7—S1121.4 (3)C11'—C10'—H10D109.9
C1—C7—S1119.5 (3)H10C—C10'—H10D108.3
N1—C8—C9112.8 (5)C12'—C11'—C10'110.1 (10)
N1—C8—C13107.5 (4)C12'—C11'—H11C109.6
C9—C8—C13108.5 (4)C10'—C11'—H11C109.6
N1—C8—H8A109.3C12'—C11'—H11D109.6
C9—C8—H8A109.3C10'—C11'—H11D109.6
C13—C8—H8A109.3H11C—C11'—H11D108.2
C8—C9—C10111.6 (4)C13'—C12'—C11'112.5 (10)
C8—C9—H9A109.3C13'—C12'—H12C109.1
C10—C9—H9A109.3C11'—C12'—H12C109.1
C8—C9—H9B109.3C13'—C12'—H12D109.1
C10—C9—H9B109.3C11'—C12'—H12D109.1
H9A—C9—H9B108.0H12C—C12'—H12D107.8
C11—C10—C9110.4 (4)C12'—C13'—C8'114.7 (10)
C11—C10—H10A109.6C12'—C13'—H13C108.6
C9—C10—H10A109.6C8'—C13'—H13C108.6
C11—C10—H10B109.6C12'—C13'—H13D108.6
C9—C10—H10B109.6C8'—C13'—H13D108.6
H10A—C10—H10B108.1H13C—C13'—H13D107.6
O2—S1—N1—C8'43.0 (18)S1—N1—C8—C974.4 (6)
O1—S1—N1—C8'171.2 (17)C8'—N1—C8—C1335 (10)
C7—S1—N1—C8'74.5 (18)S1—N1—C8—C13165.9 (4)
O2—S1—N1—C839.2 (4)N1—C8—C9—C10179.0 (5)
O1—S1—N1—C8167.3 (4)C13—C8—C9—C1059.9 (6)
C7—S1—N1—C878.4 (4)C8—C9—C10—C1157.6 (7)
C7—C1—C2—C30.9 (5)C9—C10—C11—C1252.8 (7)
C1—C2—C3—C50.4 (5)C10—C11—C12—C1352.4 (8)
C1—C2—C3—C4179.9 (3)C11—C12—C13—C854.7 (7)
C2—C3—C5—C60.6 (5)N1—C8—C13—C12179.7 (5)
C4—C3—C5—C6179.2 (3)C9—C8—C13—C1258.0 (7)
C3—C5—C6—C71.0 (5)C8—N1—C8'—C13'162 (11)
C5—C6—C7—C10.5 (5)S1—N1—C8'—C13'138.9 (15)
C5—C6—C7—S1179.4 (3)C8—N1—C8'—C9'32 (9)
C2—C1—C7—C60.4 (5)S1—N1—C8'—C9'9 (3)
C2—C1—C7—S1179.7 (3)N1—C8'—C9'—C10'180 (2)
O2—S1—C7—C63.7 (3)C13'—C8'—C9'—C10'52 (2)
O1—S1—C7—C6125.9 (3)C8'—C9'—C10'—C11'59.0 (19)
N1—S1—C7—C6120.9 (3)C9'—C10'—C11'—C12'61 (2)
O2—S1—C7—C1176.4 (3)C10'—C11'—C12'—C13'55 (2)
O1—S1—C7—C154.1 (3)C11'—C12'—C13'—C8'48 (3)
N1—S1—C7—C159.1 (3)N1—C8'—C13'—C12'178 (2)
C8'—N1—C8—C985 (10)C9'—C8'—C13'—C12'46 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.76 (3)2.20 (4)2.951 (4)172 (4)
Symmetry code: (i) x+1, y, z+1.
 

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