In the molecule of the title compound, C
20H
20N
2O
2S, 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
CCDC reference: 647308
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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
C20H20N2O2S | Z = 2 |
Mr = 352.45 | F(000) = 372 |
Triclinic, P1 | Dx = 1.294 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8386 (1) Å | Cell parameters from 25 reflections |
b = 9.8790 (2) Å | θ = 3.6–21.5° |
c = 10.5647 (2) Å | µ = 0.19 mm−1 |
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 tube | Rint = 0.021 |
Graphite monochromator | θmax = 26.3°, θmin = 2.4° |
Nonprofiled ω scans | h = −11→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −12→12 |
Tmin = 0.946, Tmax = 0.971 | l = −13→0 |
3853 measured reflections | 3 standard reflections every 120 min |
3646 independent reflections | intensity decay: 1% |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H-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 reflections | Δρmax = 0.55 e Å−3 |
229 parameters | Δρmin = −0.92 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.21450 (6) | 0.54171 (5) | 0.15718 (5) | 0.0510 (2) | |
O1 | 0.35001 (18) | 0.50195 (17) | 0.21552 (17) | 0.0676 (5) | |
O2 | 0.16276 (19) | 0.44770 (15) | 0.07632 (17) | 0.0652 (5) | |
N1 | 0.24365 (18) | 0.67589 (16) | 0.06946 (15) | 0.0459 (4) | |
N2 | 0.27653 (17) | 0.89392 (16) | 0.13913 (15) | 0.0450 (4) | |
C1 | 0.1168 (2) | 0.7353 (2) | −0.0006 (2) | 0.0488 (5) | |
H1A | 0.0571 | 0.8130 | 0.0474 | 0.059* | |
H1B | 0.0489 | 0.6678 | −0.0082 | 0.059* | |
C2 | 0.1766 (2) | 0.7812 (2) | −0.1322 (2) | 0.0469 (5) | |
C3 | 0.1045 (3) | 0.8990 (2) | −0.1823 (2) | 0.0624 (6) | |
H3 | 0.0229 | 0.9520 | −0.1324 | 0.075* | |
C4 | 0.1509 (4) | 0.9393 (3) | −0.3042 (3) | 0.0795 (8) | |
H4 | 0.1003 | 1.0190 | −0.3356 | 0.095* | |
C5 | 0.2709 (4) | 0.8635 (3) | −0.3807 (3) | 0.0782 (8) | |
C6 | 0.3452 (3) | 0.7466 (3) | −0.3311 (2) | 0.0710 (7) | |
H6 | 0.4278 | 0.6947 | −0.3809 | 0.085* | |
C7 | 0.2982 (3) | 0.7053 (2) | −0.2071 (2) | 0.0574 (5) | |
H7 | 0.3493 | 0.6261 | −0.1752 | 0.069* | |
C8 | 0.0608 (2) | 0.5953 (2) | 0.2791 (2) | 0.0508 (5) | |
C9 | −0.0883 (3) | 0.5814 (3) | 0.2613 (2) | 0.0634 (6) | |
H9 | −0.1084 | 0.5452 | 0.1854 | 0.076* | |
C10 | −0.2071 (3) | 0.6223 (3) | 0.3587 (3) | 0.0759 (7) | |
H10 | −0.3082 | 0.6143 | 0.3482 | 0.091* | |
C11 | −0.1760 (3) | 0.6746 (3) | 0.4708 (3) | 0.0781 (8) | |
H11 | −0.2563 | 0.7008 | 0.5362 | 0.094* | |
C12 | −0.0280 (4) | 0.6888 (3) | 0.4875 (3) | 0.0775 (8) | |
H12 | −0.0085 | 0.7253 | 0.5636 | 0.093* | |
C13 | 0.0916 (3) | 0.6492 (3) | 0.3919 (2) | 0.0646 (6) | |
H13 | 0.1922 | 0.6585 | 0.4029 | 0.077* | |
C14 | 0.3430 (2) | 0.7683 (2) | 0.10475 (17) | 0.0434 (4) | |
C15 | 0.4999 (2) | 0.7256 (2) | 0.0946 (2) | 0.0584 (6) | |
H15 | 0.5422 | 0.6368 | 0.0688 | 0.070* | |
C16 | 0.5914 (3) | 0.8192 (3) | 0.1241 (2) | 0.0651 (6) | |
H16 | 0.6975 | 0.7940 | 0.1199 | 0.078* | |
C17 | 0.5250 (2) | 0.9498 (3) | 0.1597 (2) | 0.0588 (6) | |
H17 | 0.5858 | 1.0140 | 0.1794 | 0.071* | |
C18 | 0.3673 (2) | 0.9851 (2) | 0.16618 (19) | 0.0510 (5) | |
C19 | 0.2899 (3) | 1.1260 (3) | 0.2034 (3) | 0.0729 (7) | |
H19A | 0.2455 | 1.1683 | 0.1323 | 0.109* | |
H19B | 0.3643 | 1.1790 | 0.2280 | 0.109* | |
H19C | 0.2101 | 1.1214 | 0.2740 | 0.109* | |
C20 | 0.3226 (5) | 0.9067 (5) | −0.5155 (3) | 0.1209 (15) | |
H20A | 0.2415 | 0.9025 | −0.5668 | 0.181* | |
H20B | 0.4130 | 0.8462 | −0.5512 | 0.181* | |
H20C | 0.3459 | 0.9985 | −0.5142 | 0.181* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0534 (3) | 0.0384 (3) | 0.0587 (4) | −0.0030 (2) | −0.0021 (2) | −0.0008 (2) |
O1 | 0.0601 (9) | 0.0576 (9) | 0.0817 (11) | 0.0034 (7) | −0.0110 (8) | 0.0149 (8) |
O2 | 0.0733 (10) | 0.0428 (8) | 0.0769 (11) | −0.0093 (7) | 0.0013 (8) | −0.0153 (7) |
N1 | 0.0457 (9) | 0.0440 (9) | 0.0485 (9) | −0.0081 (7) | −0.0065 (7) | 0.0013 (7) |
N2 | 0.0449 (8) | 0.0473 (9) | 0.0425 (8) | −0.0089 (7) | −0.0025 (7) | −0.0012 (7) |
C1 | 0.0427 (10) | 0.0469 (11) | 0.0573 (12) | −0.0066 (8) | −0.0078 (8) | −0.0033 (9) |
C2 | 0.0459 (10) | 0.0437 (10) | 0.0549 (11) | −0.0124 (8) | −0.0147 (8) | −0.0006 (9) |
C3 | 0.0621 (13) | 0.0532 (13) | 0.0765 (16) | −0.0068 (10) | −0.0273 (12) | 0.0026 (11) |
C4 | 0.096 (2) | 0.0710 (17) | 0.0856 (19) | −0.0278 (15) | −0.0456 (17) | 0.0280 (15) |
C5 | 0.097 (2) | 0.095 (2) | 0.0597 (15) | −0.0542 (17) | −0.0293 (15) | 0.0198 (14) |
C6 | 0.0711 (15) | 0.0889 (19) | 0.0571 (14) | −0.0311 (14) | −0.0022 (12) | −0.0021 (13) |
C7 | 0.0578 (12) | 0.0568 (13) | 0.0579 (13) | −0.0100 (10) | −0.0073 (10) | 0.0011 (10) |
C8 | 0.0599 (12) | 0.0415 (10) | 0.0500 (11) | −0.0091 (9) | −0.0025 (9) | 0.0041 (8) |
C9 | 0.0604 (13) | 0.0733 (15) | 0.0556 (13) | −0.0109 (11) | −0.0028 (10) | −0.0040 (11) |
C10 | 0.0607 (14) | 0.091 (2) | 0.0727 (17) | −0.0091 (13) | 0.0010 (12) | −0.0019 (14) |
C11 | 0.0821 (18) | 0.0773 (18) | 0.0663 (16) | −0.0060 (14) | 0.0157 (13) | −0.0088 (13) |
C12 | 0.096 (2) | 0.0754 (17) | 0.0608 (15) | −0.0203 (14) | 0.0002 (14) | −0.0142 (13) |
C13 | 0.0729 (15) | 0.0653 (14) | 0.0575 (13) | −0.0188 (12) | −0.0061 (11) | −0.0042 (11) |
C14 | 0.0431 (10) | 0.0483 (11) | 0.0385 (9) | −0.0074 (8) | −0.0040 (7) | 0.0015 (8) |
C15 | 0.0450 (11) | 0.0610 (13) | 0.0660 (14) | −0.0018 (9) | −0.0025 (9) | −0.0010 (11) |
C16 | 0.0417 (11) | 0.0850 (17) | 0.0697 (15) | −0.0106 (11) | −0.0108 (10) | 0.0103 (13) |
C17 | 0.0566 (12) | 0.0755 (16) | 0.0512 (12) | −0.0279 (11) | −0.0127 (10) | 0.0034 (11) |
C18 | 0.0600 (12) | 0.0555 (12) | 0.0396 (10) | −0.0185 (9) | −0.0031 (9) | −0.0005 (8) |
C19 | 0.0805 (17) | 0.0571 (14) | 0.0821 (17) | −0.0204 (12) | −0.0027 (14) | −0.0107 (12) |
C20 | 0.162 (3) | 0.153 (4) | 0.072 (2) | −0.094 (3) | −0.031 (2) | 0.039 (2) |
Geometric parameters (Å, º) top
S1—O1 | 1.4247 (17) | C9—C10 | 1.384 (3) |
S1—O2 | 1.4285 (17) | C9—H9 | 0.9300 |
S1—N1 | 1.6426 (17) | C10—H10 | 0.9300 |
S1—C8 | 1.765 (2) | C11—C12 | 1.370 (4) |
N1—C1 | 1.476 (2) | C11—C10 | 1.372 (4) |
N1—C14 | 1.438 (2) | C11—H11 | 0.9300 |
N2—C14 | 1.325 (2) | C12—H12 | 0.9300 |
N2—C18 | 1.346 (3) | C13—C12 | 1.374 (4) |
C1—C2 | 1.509 (3) | C13—H13 | 0.9300 |
C1—H1A | 0.9700 | C14—C15 | 1.380 (3) |
C1—H1B | 0.9700 | C15—C16 | 1.376 (3) |
C2—C7 | 1.375 (3) | C15—H15 | 0.9300 |
C2—C3 | 1.383 (3) | C16—H16 | 0.9300 |
C3—C4 | 1.372 (4) | C17—C16 | 1.372 (4) |
C3—H3 | 0.9300 | C17—H17 | 0.9300 |
C4—H4 | 0.9300 | C18—C17 | 1.380 (3) |
C5—C4 | 1.374 (4) | C18—C19 | 1.490 (3) |
C5—C6 | 1.381 (4) | C19—H19A | 0.9600 |
C5—C20 | 1.513 (4) | C19—H19B | 0.9600 |
C6—H6 | 0.9300 | C19—H19C | 0.9600 |
C7—C6 | 1.395 (3) | C20—H20A | 0.9600 |
C7—H7 | 0.9300 | C20—H20B | 0.9600 |
C8—C9 | 1.382 (3) | C20—H20C | 0.9600 |
C8—C13 | 1.384 (3) | | |
| | | |
O1—S1—O2 | 120.14 (11) | C11—C10—C9 | 120.1 (3) |
O1—S1—N1 | 107.14 (9) | C11—C10—H10 | 119.9 |
O2—S1—N1 | 106.16 (9) | C9—C10—H10 | 119.9 |
O1—S1—C8 | 108.06 (11) | C12—C11—C10 | 120.8 (2) |
O2—S1—C8 | 107.52 (10) | C12—C11—H11 | 119.6 |
N1—S1—C8 | 107.18 (9) | C10—C11—H11 | 119.6 |
C14—N1—C1 | 116.45 (15) | C11—C12—C13 | 120.0 (3) |
C14—N1—S1 | 120.32 (13) | C11—C12—H12 | 120.0 |
C1—N1—S1 | 116.64 (13) | C13—C12—H12 | 120.0 |
C14—N2—C18 | 118.06 (17) | C12—C13—C8 | 119.4 (2) |
N1—C1—C2 | 111.68 (15) | C12—C13—H13 | 120.3 |
N1—C1—H1A | 109.3 | C8—C13—H13 | 120.3 |
C2—C1—H1A | 109.3 | N2—C14—C15 | 123.93 (19) |
N1—C1—H1B | 109.3 | N2—C14—N1 | 116.51 (16) |
C2—C1—H1B | 109.3 | C15—C14—N1 | 119.46 (18) |
H1A—C1—H1B | 107.9 | C16—C15—C14 | 117.5 (2) |
C7—C2—C3 | 118.3 (2) | C16—C15—H15 | 121.2 |
C7—C2—C1 | 121.65 (19) | C14—C15—H15 | 121.2 |
C3—C2—C1 | 119.9 (2) | C17—C16—C15 | 119.5 (2) |
C4—C3—C2 | 121.3 (3) | C17—C16—H16 | 120.3 |
C4—C3—H3 | 119.4 | C15—C16—H16 | 120.3 |
C2—C3—H3 | 119.4 | C16—C17—C18 | 119.5 (2) |
C3—C4—C5 | 121.0 (3) | C16—C17—H17 | 120.2 |
C3—C4—H4 | 119.5 | C18—C17—H17 | 120.2 |
C5—C4—H4 | 119.5 | N2—C18—C17 | 121.5 (2) |
C4—C5—C6 | 118.3 (2) | N2—C18—C19 | 117.04 (19) |
C4—C5—C20 | 121.4 (3) | C17—C18—C19 | 121.5 (2) |
C6—C5—C20 | 120.3 (3) | C18—C19—H19A | 109.5 |
C5—C6—C7 | 120.9 (3) | C18—C19—H19B | 109.5 |
C5—C6—H6 | 119.5 | H19A—C19—H19B | 109.5 |
C7—C6—H6 | 119.5 | C18—C19—H19C | 109.5 |
C2—C7—C6 | 120.2 (2) | H19A—C19—H19C | 109.5 |
C2—C7—H7 | 119.9 | H19B—C19—H19C | 109.5 |
C6—C7—H7 | 119.9 | C5—C20—H20A | 109.5 |
C9—C8—C13 | 120.9 (2) | C5—C20—H20B | 109.5 |
C9—C8—S1 | 119.63 (18) | H20A—C20—H20B | 109.5 |
C13—C8—S1 | 119.48 (18) | C5—C20—H20C | 109.5 |
C8—C9—C10 | 118.8 (2) | H20A—C20—H20C | 109.5 |
C8—C9—H9 | 120.6 | H20B—C20—H20C | 109.5 |
C10—C9—H9 | 120.6 | | |
| | | |
O1—S1—N1—C14 | −29.40 (17) | N1—C14—C15—C16 | 177.25 (19) |
O2—S1—N1—C14 | −158.93 (14) | C7—C2—C3—C4 | 0.8 (3) |
C8—S1—N1—C14 | 86.38 (16) | C1—C2—C3—C4 | −176.4 (2) |
O1—S1—N1—C1 | −179.94 (14) | C3—C2—C7—C6 | −0.7 (3) |
O2—S1—N1—C1 | 50.53 (16) | C1—C2—C7—C6 | 176.4 (2) |
C8—S1—N1—C1 | −64.15 (16) | C2—C3—C4—C5 | 0.0 (4) |
O1—S1—C8—C9 | −151.33 (18) | C6—C5—C4—C3 | −0.9 (4) |
O2—S1—C8—C9 | −20.3 (2) | C20—C5—C4—C3 | 179.7 (3) |
N1—S1—C8—C9 | 93.50 (19) | C4—C5—C6—C7 | 0.9 (4) |
O1—S1—C8—C13 | 27.8 (2) | C20—C5—C6—C7 | −179.6 (2) |
O2—S1—C8—C13 | 158.89 (18) | C2—C7—C6—C5 | −0.2 (4) |
N1—S1—C8—C13 | −87.33 (19) | C13—C8—C9—C10 | 0.0 (4) |
C1—N1—C14—N2 | 36.7 (2) | S1—C8—C9—C10 | 179.1 (2) |
S1—N1—C14—N2 | −113.92 (17) | C9—C8—C13—C12 | 0.2 (4) |
C1—N1—C14—C15 | −139.79 (19) | S1—C8—C13—C12 | −178.9 (2) |
S1—N1—C14—C15 | 69.6 (2) | C8—C9—C10—C11 | −0.5 (4) |
C14—N1—C1—C2 | 67.3 (2) | C12—C11—C10—C9 | 0.8 (5) |
S1—N1—C1—C2 | −141.01 (14) | C10—C11—C12—C13 | −0.6 (5) |
C18—N2—C14—C15 | −0.2 (3) | C8—C13—C12—C11 | 0.1 (4) |
C18—N2—C14—N1 | −176.52 (16) | N2—C14—C15—C16 | 1.1 (3) |
C14—N2—C18—C17 | −0.6 (3) | C14—C15—C16—C17 | −1.1 (3) |
C14—N2—C18—C19 | 179.5 (2) | C18—C17—C16—C15 | 0.4 (3) |
N1—C1—C2—C7 | 40.1 (3) | N2—C18—C17—C16 | 0.5 (3) |
N1—C1—C2—C3 | −142.77 (19) | C19—C18—C17—C16 | −179.5 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1B···O2i | 0.97 | 2.51 | 3.443 (2) | 161 |
Symmetry code: (i) −x, −y+1, −z. |