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In the structure of N-but­yl-N-o-tolylbenzene­sulfonamide, C17H21NO2S, the mean planes of the benzene rings are inclined to each other at 40.3 (1)°. The geometry around the S atom is considerably distorted from ideal tetra­hedral geometry. Centrosymmetrically related pairs of mol­ecules dimerize through C—H...O hydrogen bonds. The crystal packing is stabilized by inter­molecular C—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501562X/bt6659sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680501562X/bt6659Isup2.hkl
Contains datablock I

CCDC reference: 274340

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.061
  • wR factor = 0.179
  • Data-to-parameter ratio = 18.9

checkCIF/PLATON results

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Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.22 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.01 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 6.38 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 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 2 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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

N-Butyl-N-o-tolyl-benzenesulfonamide top
Crystal data top
C17H21NO2SF(000) = 648
Mr = 303.41Dx = 1.214 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2765 reflections
a = 9.2614 (9) Åθ = 2.2–28°
b = 18.4306 (19) ŵ = 0.20 mm1
c = 9.8602 (10) ÅT = 273 K
β = 99.382 (2)°Block, white
V = 1660.6 (3) Å30.23 × 0.21 × 0.20 mm
Z = 4
Data collection top
CCD area-detector
diffractometer
2765 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 28.0°, θmin = 2.2°
ω scansh = 911
9999 measured reflectionsk = 2423
3635 independent reflectionsl = 1212
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.179H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1P)2 + 0.3505P]
where P = (Fo2 + 2Fc2)/3
3635 reflections(Δ/σ)max < 0.001
192 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.22 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*/Ueq
S10.63749 (6)0.13146 (3)0.45717 (6)0.0555 (2)
O10.49855 (17)0.09665 (11)0.4499 (2)0.0763 (5)
O20.6445 (2)0.20749 (9)0.4342 (2)0.0721 (5)
N10.72100 (19)0.09188 (9)0.34317 (19)0.0521 (5)
C10.8570 (2)0.12466 (10)0.3183 (2)0.0508 (5)
C20.9873 (2)0.10479 (13)0.3998 (3)0.0601 (6)
H20.98620.07190.47120.072*
C31.1180 (3)0.13304 (16)0.3762 (4)0.0804 (8)
H31.20520.11900.43070.097*
C41.1192 (4)0.1813 (2)0.2735 (4)0.0990 (12)
H41.20770.20050.25730.119*
C50.9915 (5)0.20217 (17)0.1931 (3)0.0947 (11)
H50.99540.23580.12340.114*
C60.8534 (3)0.17445 (13)0.2120 (3)0.0691 (7)
C70.7165 (5)0.1969 (2)0.1234 (3)0.1041 (11)
H7A0.65530.15530.10020.156*
H7B0.73910.21860.04080.156*
H7C0.66620.23150.17150.156*
C80.7392 (2)0.11350 (12)0.6200 (2)0.0525 (5)
C90.8419 (3)0.16331 (13)0.6812 (3)0.0633 (6)
H90.85630.20650.63660.076*
C100.9219 (3)0.14852 (16)0.8076 (3)0.0779 (8)
H100.99080.18180.84910.094*
C110.9006 (4)0.08500 (18)0.8727 (3)0.0862 (9)
H110.95430.07550.95900.103*
C120.8003 (4)0.03488 (17)0.8116 (3)0.0846 (9)
H120.78790.00860.85630.102*
C130.7192 (3)0.04848 (13)0.6861 (3)0.0662 (7)
H130.65130.01470.64500.079*
C140.7113 (3)0.01170 (12)0.3346 (3)0.0618 (6)
H14A0.80010.00900.38580.074*
H14B0.63000.00440.37770.074*
C150.6912 (4)0.01596 (14)0.1925 (3)0.0825 (8)
H15A0.77520.00260.15070.099*
H15B0.60530.00650.13960.099*
C160.6730 (4)0.09852 (16)0.1876 (4)0.0993 (11)
H16A0.75750.12030.24410.119*
H16B0.58750.11120.22790.119*
C170.6570 (6)0.1300 (2)0.0497 (5)0.1449 (19)
H17A0.57970.10560.00970.217*
H17B0.63400.18070.05400.217*
H17C0.74700.12440.01420.217*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0447 (3)0.0535 (3)0.0704 (4)0.0066 (2)0.0157 (3)0.0014 (2)
O10.0415 (9)0.0960 (14)0.0925 (14)0.0017 (8)0.0145 (9)0.0028 (11)
O20.0782 (12)0.0548 (10)0.0858 (13)0.0207 (8)0.0209 (10)0.0006 (8)
N10.0511 (10)0.0440 (9)0.0637 (11)0.0010 (7)0.0163 (9)0.0002 (8)
C10.0596 (13)0.0409 (10)0.0560 (12)0.0033 (8)0.0217 (11)0.0016 (8)
C20.0519 (13)0.0582 (13)0.0734 (16)0.0020 (10)0.0198 (12)0.0011 (11)
C30.0562 (15)0.0842 (19)0.106 (2)0.0114 (13)0.0285 (15)0.0151 (16)
C40.100 (3)0.102 (2)0.109 (3)0.052 (2)0.057 (2)0.028 (2)
C50.145 (3)0.0746 (18)0.0738 (19)0.041 (2)0.047 (2)0.0024 (15)
C60.100 (2)0.0531 (13)0.0563 (14)0.0089 (12)0.0206 (14)0.0031 (10)
C70.142 (3)0.090 (2)0.075 (2)0.006 (2)0.003 (2)0.0249 (17)
C80.0473 (12)0.0504 (11)0.0637 (13)0.0006 (9)0.0211 (10)0.0072 (9)
C90.0639 (15)0.0518 (12)0.0772 (17)0.0069 (10)0.0205 (14)0.0086 (11)
C100.0743 (18)0.0743 (17)0.083 (2)0.0112 (14)0.0058 (16)0.0233 (15)
C110.097 (2)0.087 (2)0.0697 (18)0.0006 (17)0.0016 (16)0.0057 (15)
C120.105 (2)0.0752 (17)0.0725 (19)0.0097 (16)0.0112 (17)0.0105 (14)
C130.0675 (16)0.0606 (14)0.0727 (17)0.0131 (11)0.0176 (14)0.0027 (11)
C140.0621 (14)0.0441 (11)0.0825 (17)0.0056 (10)0.0218 (13)0.0006 (11)
C150.097 (2)0.0582 (15)0.090 (2)0.0001 (14)0.0075 (17)0.0148 (14)
C160.109 (3)0.0638 (17)0.127 (3)0.0002 (16)0.025 (2)0.0254 (18)
C170.171 (4)0.080 (2)0.166 (5)0.013 (2)0.024 (4)0.041 (3)
Geometric parameters (Å, º) top
S1—O21.423 (2)C9—C101.369 (4)
S1—O11.429 (2)C9—H90.9300
S1—N11.636 (2)C10—C111.365 (4)
S1—C81.755 (3)C10—H100.9300
N1—C11.454 (3)C11—C121.377 (4)
N1—C141.482 (3)C11—H110.9300
C1—C21.385 (3)C12—C131.362 (4)
C1—C61.390 (3)C12—H120.9300
C2—C31.372 (3)C13—H130.9300
C2—H20.9300C14—C151.473 (4)
C3—C41.349 (5)C14—H14A0.9700
C3—H30.9300C14—H14B0.9700
C4—C51.368 (5)C15—C161.531 (4)
C4—H40.9300C15—H15A0.9700
C5—C61.417 (4)C15—H15B0.9700
C5—H50.9300C16—C171.464 (5)
C6—C71.477 (5)C16—H16A0.9700
C7—H7A0.9600C16—H16B0.9700
C7—H7B0.9600C17—H17A0.9600
C7—H7C0.9600C17—H17B0.9600
C8—C91.387 (3)C17—H17C0.9600
C8—C131.391 (3)
O2—S1—O1119.9 (1)C8—C9—H9120.2
O2—S1—N1106.9 (1)C11—C10—C9120.0 (3)
O1—S1—N1106.7 (1)C11—C10—H10120.0
O2—S1—C8107.4 (1)C9—C10—H10120.0
O1—S1—C8107.8 (1)C10—C11—C12120.6 (3)
N1—S1—C8107.5 (1)C10—C11—H11119.7
C1—N1—C14116.8 (2)C12—C11—H11119.7
C1—N1—S1116.8 (1)C13—C12—C11120.4 (3)
C14—N1—S1116.9 (1)C13—C12—H12119.8
C2—C1—C6121.6 (2)C11—C12—H12119.8
C2—C1—N1119.31 (19)C12—C13—C8119.3 (2)
C6—C1—N1119.1 (2)C12—C13—H13120.4
C3—C2—C1120.7 (3)C8—C13—H13120.4
C3—C2—H2119.6C15—C14—N1113.4 (2)
C1—C2—H2119.6C15—C14—H14A108.9
C4—C3—C2119.5 (3)N1—C14—H14A108.9
C4—C3—H3120.2C15—C14—H14B108.9
C2—C3—H3120.2N1—C14—H14B108.9
C3—C4—C5120.6 (3)H14A—C14—H14B107.7
C3—C4—H4119.7C14—C15—C16111.7 (3)
C5—C4—H4119.7C14—C15—H15A109.3
C4—C5—C6122.4 (3)C16—C15—H15A109.3
C4—C5—H5118.8C14—C15—H15B109.3
C6—C5—H5118.8C16—C15—H15B109.3
C1—C6—C5115.2 (3)H15A—C15—H15B107.9
C1—C6—C7123.0 (3)C17—C16—C15114.7 (3)
C5—C6—C7121.8 (3)C17—C16—H16A108.6
C6—C7—H7A109.5C15—C16—H16A108.6
C6—C7—H7B109.5C17—C16—H16B108.6
H7A—C7—H7B109.5C15—C16—H16B108.6
C6—C7—H7C109.5H16A—C16—H16B107.6
H7A—C7—H7C109.5C16—C17—H17A109.5
H7B—C7—H7C109.5C16—C17—H17B109.5
C9—C8—C13120.0 (2)H17A—C17—H17B109.5
C9—C8—S1120.06 (19)C16—C17—H17C109.5
C13—C8—S1119.92 (18)H17A—C17—H17C109.5
C10—C9—C8119.7 (2)H17B—C17—H17C109.5
C10—C9—H9120.2
O2—S1—N1—C142.44 (19)C4—C5—C6—C7179.4 (3)
O1—S1—N1—C1171.89 (16)O2—S1—C8—C919.5 (2)
C8—S1—N1—C172.67 (18)O1—S1—C8—C9149.98 (18)
O2—S1—N1—C14172.24 (17)N1—S1—C8—C995.3 (2)
O1—S1—N1—C1442.8 (2)O2—S1—C8—C13162.08 (18)
C8—S1—N1—C1472.7 (2)O1—S1—C8—C1331.6 (2)
C14—N1—C1—C258.0 (3)N1—S1—C8—C1383.2 (2)
S1—N1—C1—C287.3 (2)C13—C8—C9—C100.9 (4)
C14—N1—C1—C6121.0 (2)S1—C8—C9—C10179.3 (2)
S1—N1—C1—C693.6 (2)C8—C9—C10—C110.1 (4)
C6—C1—C2—C31.1 (4)C9—C10—C11—C120.9 (5)
N1—C1—C2—C3178.0 (2)C10—C11—C12—C131.0 (5)
C1—C2—C3—C40.7 (4)C11—C12—C13—C80.2 (5)
C2—C3—C4—C50.0 (5)C9—C8—C13—C120.7 (4)
C3—C4—C5—C60.5 (5)S1—C8—C13—C12179.1 (2)
C2—C1—C6—C50.6 (3)C1—N1—C14—C1574.7 (3)
N1—C1—C6—C5178.4 (2)S1—N1—C14—C15140.0 (2)
C2—C1—C6—C7179.9 (3)N1—C14—C15—C16176.8 (2)
N1—C1—C6—C71.1 (4)C14—C15—C16—C17178.2 (3)
C4—C5—C6—C10.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O2i0.932.553.466 (3)168
C13—H13···O1ii0.932.573.484 (3)169
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y, z+1.
 

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