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In the mol­ecule of the title compound, C20H20N2O2S, with rings A (4-methyl­benzyl aromatic ring), B (benzene­sulfonamide aromatic ring) and C (pyridine), the dihedral angles are A/B = 71.12 (9), A/C = 80.50 (8) and B/C = 50.95 (7)°. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules into centrosymmetric dimers, which may be effective in the stabilization of the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015395/rk2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015395/rk2009Isup2.hkl
Contains datablock I

CCDC reference: 647308

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.065
  • wR factor = 0.163
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.78 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.07 Ratio
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 0 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 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

N-(4-Methylbenzyl)-N-(6-methyl-2-pyridyl)benzenesulfonamide top
Crystal data top
C20H20N2O2SZ = 2
Mr = 352.45F(000) = 372
Triclinic, P1Dx = 1.294 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8386 (1) ÅCell parameters from 25 reflections
b = 9.8790 (2) Åθ = 3.6–21.5°
c = 10.5647 (2) ŵ = 0.19 mm1
α = 89.589 (5)°T = 294 K
β = 82.226 (6)°Prism, orange
γ = 81.737 (8)°0.35 × 0.25 × 0.15 mm
V = 904.44 (4) Å3
Data collection top
Enraf–Nonius TurboCAD4
diffractometer
2890 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 26.3°, θmin = 2.4°
Nonprofiled ω scansh = 1110
Absorption correction: ψ scan
(North et al., 1968)
k = 1212
Tmin = 0.946, Tmax = 0.971l = 130
3853 measured reflections3 standard reflections every 120 min
3646 independent reflections intensity decay: 1%
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)] = 0.065H-atom parameters constrained
wR(F2) = 0.163 w = 1/[σ2(Fo2) + (0.0977P)2 + 0.0839P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
3646 reflectionsΔρmax = 0.55 e Å3
229 parametersΔρmin = 0.92 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.135 (11)
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
S10.21450 (6)0.54171 (5)0.15718 (5)0.0510 (2)
O10.35001 (18)0.50195 (17)0.21552 (17)0.0676 (5)
O20.16276 (19)0.44770 (15)0.07632 (17)0.0652 (5)
N10.24365 (18)0.67589 (16)0.06946 (15)0.0459 (4)
N20.27653 (17)0.89392 (16)0.13913 (15)0.0450 (4)
C10.1168 (2)0.7353 (2)0.0006 (2)0.0488 (5)
H1A0.05710.81300.04740.059*
H1B0.04890.66780.00820.059*
C20.1766 (2)0.7812 (2)0.1322 (2)0.0469 (5)
C30.1045 (3)0.8990 (2)0.1823 (2)0.0624 (6)
H30.02290.95200.13240.075*
C40.1509 (4)0.9393 (3)0.3042 (3)0.0795 (8)
H40.10031.01900.33560.095*
C50.2709 (4)0.8635 (3)0.3807 (3)0.0782 (8)
C60.3452 (3)0.7466 (3)0.3311 (2)0.0710 (7)
H60.42780.69470.38090.085*
C70.2982 (3)0.7053 (2)0.2071 (2)0.0574 (5)
H70.34930.62610.17520.069*
C80.0608 (2)0.5953 (2)0.2791 (2)0.0508 (5)
C90.0883 (3)0.5814 (3)0.2613 (2)0.0634 (6)
H90.10840.54520.18540.076*
C100.2071 (3)0.6223 (3)0.3587 (3)0.0759 (7)
H100.30820.61430.34820.091*
C110.1760 (3)0.6746 (3)0.4708 (3)0.0781 (8)
H110.25630.70080.53620.094*
C120.0280 (4)0.6888 (3)0.4875 (3)0.0775 (8)
H120.00850.72530.56360.093*
C130.0916 (3)0.6492 (3)0.3919 (2)0.0646 (6)
H130.19220.65850.40290.077*
C140.3430 (2)0.7683 (2)0.10475 (17)0.0434 (4)
C150.4999 (2)0.7256 (2)0.0946 (2)0.0584 (6)
H150.54220.63680.06880.070*
C160.5914 (3)0.8192 (3)0.1241 (2)0.0651 (6)
H160.69750.79400.11990.078*
C170.5250 (2)0.9498 (3)0.1597 (2)0.0588 (6)
H170.58581.01400.17940.071*
C180.3673 (2)0.9851 (2)0.16618 (19)0.0510 (5)
C190.2899 (3)1.1260 (3)0.2034 (3)0.0729 (7)
H19A0.24551.16830.13230.109*
H19B0.36431.17900.22800.109*
H19C0.21011.12140.27400.109*
C200.3226 (5)0.9067 (5)0.5155 (3)0.1209 (15)
H20A0.24150.90250.56680.181*
H20B0.41300.84620.55120.181*
H20C0.34590.99850.51420.181*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0534 (3)0.0384 (3)0.0587 (4)0.0030 (2)0.0021 (2)0.0008 (2)
O10.0601 (9)0.0576 (9)0.0817 (11)0.0034 (7)0.0110 (8)0.0149 (8)
O20.0733 (10)0.0428 (8)0.0769 (11)0.0093 (7)0.0013 (8)0.0153 (7)
N10.0457 (9)0.0440 (9)0.0485 (9)0.0081 (7)0.0065 (7)0.0013 (7)
N20.0449 (8)0.0473 (9)0.0425 (8)0.0089 (7)0.0025 (7)0.0012 (7)
C10.0427 (10)0.0469 (11)0.0573 (12)0.0066 (8)0.0078 (8)0.0033 (9)
C20.0459 (10)0.0437 (10)0.0549 (11)0.0124 (8)0.0147 (8)0.0006 (9)
C30.0621 (13)0.0532 (13)0.0765 (16)0.0068 (10)0.0273 (12)0.0026 (11)
C40.096 (2)0.0710 (17)0.0856 (19)0.0278 (15)0.0456 (17)0.0280 (15)
C50.097 (2)0.095 (2)0.0597 (15)0.0542 (17)0.0293 (15)0.0198 (14)
C60.0711 (15)0.0889 (19)0.0571 (14)0.0311 (14)0.0022 (12)0.0021 (13)
C70.0578 (12)0.0568 (13)0.0579 (13)0.0100 (10)0.0073 (10)0.0011 (10)
C80.0599 (12)0.0415 (10)0.0500 (11)0.0091 (9)0.0025 (9)0.0041 (8)
C90.0604 (13)0.0733 (15)0.0556 (13)0.0109 (11)0.0028 (10)0.0040 (11)
C100.0607 (14)0.091 (2)0.0727 (17)0.0091 (13)0.0010 (12)0.0019 (14)
C110.0821 (18)0.0773 (18)0.0663 (16)0.0060 (14)0.0157 (13)0.0088 (13)
C120.096 (2)0.0754 (17)0.0608 (15)0.0203 (14)0.0002 (14)0.0142 (13)
C130.0729 (15)0.0653 (14)0.0575 (13)0.0188 (12)0.0061 (11)0.0042 (11)
C140.0431 (10)0.0483 (11)0.0385 (9)0.0074 (8)0.0040 (7)0.0015 (8)
C150.0450 (11)0.0610 (13)0.0660 (14)0.0018 (9)0.0025 (9)0.0010 (11)
C160.0417 (11)0.0850 (17)0.0697 (15)0.0106 (11)0.0108 (10)0.0103 (13)
C170.0566 (12)0.0755 (16)0.0512 (12)0.0279 (11)0.0127 (10)0.0034 (11)
C180.0600 (12)0.0555 (12)0.0396 (10)0.0185 (9)0.0031 (9)0.0005 (8)
C190.0805 (17)0.0571 (14)0.0821 (17)0.0204 (12)0.0027 (14)0.0107 (12)
C200.162 (3)0.153 (4)0.072 (2)0.094 (3)0.031 (2)0.039 (2)
Geometric parameters (Å, º) top
S1—O11.4247 (17)C9—C101.384 (3)
S1—O21.4285 (17)C9—H90.9300
S1—N11.6426 (17)C10—H100.9300
S1—C81.765 (2)C11—C121.370 (4)
N1—C11.476 (2)C11—C101.372 (4)
N1—C141.438 (2)C11—H110.9300
N2—C141.325 (2)C12—H120.9300
N2—C181.346 (3)C13—C121.374 (4)
C1—C21.509 (3)C13—H130.9300
C1—H1A0.9700C14—C151.380 (3)
C1—H1B0.9700C15—C161.376 (3)
C2—C71.375 (3)C15—H150.9300
C2—C31.383 (3)C16—H160.9300
C3—C41.372 (4)C17—C161.372 (4)
C3—H30.9300C17—H170.9300
C4—H40.9300C18—C171.380 (3)
C5—C41.374 (4)C18—C191.490 (3)
C5—C61.381 (4)C19—H19A0.9600
C5—C201.513 (4)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C61.395 (3)C20—H20A0.9600
C7—H70.9300C20—H20B0.9600
C8—C91.382 (3)C20—H20C0.9600
C8—C131.384 (3)
O1—S1—O2120.14 (11)C11—C10—C9120.1 (3)
O1—S1—N1107.14 (9)C11—C10—H10119.9
O2—S1—N1106.16 (9)C9—C10—H10119.9
O1—S1—C8108.06 (11)C12—C11—C10120.8 (2)
O2—S1—C8107.52 (10)C12—C11—H11119.6
N1—S1—C8107.18 (9)C10—C11—H11119.6
C14—N1—C1116.45 (15)C11—C12—C13120.0 (3)
C14—N1—S1120.32 (13)C11—C12—H12120.0
C1—N1—S1116.64 (13)C13—C12—H12120.0
C14—N2—C18118.06 (17)C12—C13—C8119.4 (2)
N1—C1—C2111.68 (15)C12—C13—H13120.3
N1—C1—H1A109.3C8—C13—H13120.3
C2—C1—H1A109.3N2—C14—C15123.93 (19)
N1—C1—H1B109.3N2—C14—N1116.51 (16)
C2—C1—H1B109.3C15—C14—N1119.46 (18)
H1A—C1—H1B107.9C16—C15—C14117.5 (2)
C7—C2—C3118.3 (2)C16—C15—H15121.2
C7—C2—C1121.65 (19)C14—C15—H15121.2
C3—C2—C1119.9 (2)C17—C16—C15119.5 (2)
C4—C3—C2121.3 (3)C17—C16—H16120.3
C4—C3—H3119.4C15—C16—H16120.3
C2—C3—H3119.4C16—C17—C18119.5 (2)
C3—C4—C5121.0 (3)C16—C17—H17120.2
C3—C4—H4119.5C18—C17—H17120.2
C5—C4—H4119.5N2—C18—C17121.5 (2)
C4—C5—C6118.3 (2)N2—C18—C19117.04 (19)
C4—C5—C20121.4 (3)C17—C18—C19121.5 (2)
C6—C5—C20120.3 (3)C18—C19—H19A109.5
C5—C6—C7120.9 (3)C18—C19—H19B109.5
C5—C6—H6119.5H19A—C19—H19B109.5
C7—C6—H6119.5C18—C19—H19C109.5
C2—C7—C6120.2 (2)H19A—C19—H19C109.5
C2—C7—H7119.9H19B—C19—H19C109.5
C6—C7—H7119.9C5—C20—H20A109.5
C9—C8—C13120.9 (2)C5—C20—H20B109.5
C9—C8—S1119.63 (18)H20A—C20—H20B109.5
C13—C8—S1119.48 (18)C5—C20—H20C109.5
C8—C9—C10118.8 (2)H20A—C20—H20C109.5
C8—C9—H9120.6H20B—C20—H20C109.5
C10—C9—H9120.6
O1—S1—N1—C1429.40 (17)N1—C14—C15—C16177.25 (19)
O2—S1—N1—C14158.93 (14)C7—C2—C3—C40.8 (3)
C8—S1—N1—C1486.38 (16)C1—C2—C3—C4176.4 (2)
O1—S1—N1—C1179.94 (14)C3—C2—C7—C60.7 (3)
O2—S1—N1—C150.53 (16)C1—C2—C7—C6176.4 (2)
C8—S1—N1—C164.15 (16)C2—C3—C4—C50.0 (4)
O1—S1—C8—C9151.33 (18)C6—C5—C4—C30.9 (4)
O2—S1—C8—C920.3 (2)C20—C5—C4—C3179.7 (3)
N1—S1—C8—C993.50 (19)C4—C5—C6—C70.9 (4)
O1—S1—C8—C1327.8 (2)C20—C5—C6—C7179.6 (2)
O2—S1—C8—C13158.89 (18)C2—C7—C6—C50.2 (4)
N1—S1—C8—C1387.33 (19)C13—C8—C9—C100.0 (4)
C1—N1—C14—N236.7 (2)S1—C8—C9—C10179.1 (2)
S1—N1—C14—N2113.92 (17)C9—C8—C13—C120.2 (4)
C1—N1—C14—C15139.79 (19)S1—C8—C13—C12178.9 (2)
S1—N1—C14—C1569.6 (2)C8—C9—C10—C110.5 (4)
C14—N1—C1—C267.3 (2)C12—C11—C10—C90.8 (5)
S1—N1—C1—C2141.01 (14)C10—C11—C12—C130.6 (5)
C18—N2—C14—C150.2 (3)C8—C13—C12—C110.1 (4)
C18—N2—C14—N1176.52 (16)N2—C14—C15—C161.1 (3)
C14—N2—C18—C170.6 (3)C14—C15—C16—C171.1 (3)
C14—N2—C18—C19179.5 (2)C18—C17—C16—C150.4 (3)
N1—C1—C2—C740.1 (3)N2—C18—C17—C160.5 (3)
N1—C1—C2—C3142.77 (19)C19—C18—C17—C16179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1B···O2i0.972.513.443 (2)161
Symmetry code: (i) x, y+1, z.
 

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