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The S atom of the sulfonyl group in the title compound, C20H24Cl2N2O3S, has a distorted tetra­hedral geometry. Two inter­molecular N—H...O hydrogen bonds between the amino groups and the carbonyl groups link the mol­ecules into a centrosymmetric dimer.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022380/bt2099sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022380/bt2099Isup2.hkl
Contains datablock I

CCDC reference: 613590

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.132
  • Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.71 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.42 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C11 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 6 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 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, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

3-(2,4-dichlorophenyl)-N,N-diethyl-3-(4-methylphenylsulfonylamino)propanamide top
Crystal data top
C20H24Cl2N2O3SZ = 2
Mr = 443.38F(000) = 464
Triclinic, P1Dx = 1.342 Mg m3
Hall symbol: -P 1Melting point: 358 K
a = 7.895 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.704 (4) ÅCell parameters from 3856 reflections
c = 14.046 (4) Åθ = 2.7–26.3°
α = 105.881 (5)°µ = 0.41 mm1
β = 100.025 (4)°T = 294 K
γ = 99.190 (4)°Needle, colourless
V = 1097.0 (7) Å30.36 × 0.22 × 0.14 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3833 independent reflections
Radiation source: fine-focus sealed tube3131 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.896, Tmax = 0.944k = 1212
5569 measured reflectionsl = 167
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0549P)2 + 0.8034P]
where P = (Fo2 + 2Fc2)/3
3833 reflections(Δ/σ)max < 0.001
258 parametersΔρmax = 0.60 e Å3
0 restraintsΔρmin = 0.71 e Å3
Special details top

Experimental. IR (KBr, ν cm-1): 3276, 1624, 1326, 1161. (IR spectra were recorded on a BIO-RAD FTS 3000 IR spectrophotometer). 1H NMR (CDCl3): δ 7.61–7.00 (m, 7H), 4.05 (t, 1H), 3.24 (q, 2H), 3.05 (q, 2H), 2.71 (dd, 2H), 2.36 (s, 3H), 0.96 (t, 6H).

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
S10.22167 (9)0.20574 (8)0.32756 (5)0.0487 (2)
Cl10.68534 (18)0.04613 (9)0.21142 (8)0.0924 (4)
Cl20.64826 (14)0.33280 (12)0.04525 (7)0.0886 (4)
O10.2399 (3)0.0731 (2)0.31977 (19)0.0710 (7)
O20.0985 (3)0.2613 (3)0.37993 (17)0.0743 (7)
O30.6266 (3)0.4364 (2)0.60047 (14)0.0560 (5)
N10.4104 (3)0.3030 (2)0.38478 (16)0.0393 (5)
H10.407 (4)0.379 (3)0.399 (2)0.047*
N20.7407 (3)0.2568 (2)0.58579 (16)0.0420 (5)
C10.6478 (4)0.1914 (3)0.1878 (2)0.0468 (6)
C20.6632 (4)0.2046 (3)0.0942 (2)0.0595 (8)
H20.69250.13760.04620.071*
C30.6347 (4)0.3176 (3)0.0738 (2)0.0543 (8)
C40.5972 (4)0.4180 (3)0.1444 (2)0.0594 (8)
H40.58200.49610.13040.071*
C50.5817 (4)0.4028 (3)0.2373 (2)0.0513 (7)
H50.55520.47140.28530.062*
C60.6044 (3)0.2887 (2)0.26111 (19)0.0373 (6)
C70.5763 (3)0.2725 (2)0.36215 (18)0.0362 (5)
H70.57470.17980.35910.043*
C80.1713 (3)0.2170 (3)0.2031 (2)0.0448 (6)
C90.1961 (4)0.1215 (3)0.1225 (2)0.0620 (8)
H90.23000.04540.13160.074*
C100.1706 (5)0.1388 (4)0.0278 (3)0.0746 (10)
H100.18770.07350.02670.090*
C110.1207 (4)0.2494 (4)0.0116 (2)0.0610 (8)
C120.0938 (4)0.3432 (4)0.0932 (3)0.0635 (8)
H120.05850.41860.08380.076*
C130.1179 (4)0.3281 (3)0.1885 (2)0.0575 (8)
H130.09820.39240.24270.069*
C140.0963 (6)0.2666 (5)0.0930 (3)0.0983 (14)
H14A0.20650.31020.10110.147*
H14B0.01060.31950.10050.147*
H14C0.05630.18080.14370.147*
C150.7288 (3)0.3619 (3)0.44990 (19)0.0400 (6)
H15A0.83770.33460.44040.048*
H15B0.74130.45330.44910.048*
C160.6979 (3)0.3545 (3)0.55141 (18)0.0389 (6)
C170.8383 (4)0.1608 (3)0.5393 (2)0.0569 (8)
H17A0.82860.15680.46860.068*
H17B0.78530.07320.54060.068*
C181.0297 (5)0.1954 (5)0.5923 (3)0.0907 (13)
H18A1.08090.28450.59560.136*
H18B1.09000.13450.55530.136*
H18C1.04060.18930.66000.136*
C190.6905 (4)0.2458 (3)0.6794 (2)0.0568 (8)
H19A0.71250.33400.72790.068*
H19B0.76310.19490.70900.068*
C200.5017 (5)0.1802 (5)0.6603 (3)0.0954 (14)
H20A0.42920.23120.63200.143*
H20B0.47390.17510.72320.143*
H20C0.47990.09220.61340.143*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0428 (4)0.0643 (5)0.0477 (4)0.0106 (3)0.0162 (3)0.0283 (4)
Cl10.1743 (11)0.0599 (5)0.0848 (7)0.0619 (6)0.0825 (7)0.0360 (5)
Cl20.1023 (7)0.1416 (10)0.0510 (5)0.0433 (7)0.0357 (5)0.0562 (6)
O10.0728 (15)0.0623 (14)0.0836 (17)0.0018 (11)0.0112 (13)0.0434 (13)
O20.0505 (12)0.130 (2)0.0618 (14)0.0314 (13)0.0310 (11)0.0433 (14)
O30.0835 (15)0.0513 (12)0.0408 (11)0.0347 (11)0.0204 (10)0.0112 (9)
N10.0440 (12)0.0471 (13)0.0332 (11)0.0186 (11)0.0146 (9)0.0146 (10)
N20.0491 (13)0.0476 (13)0.0344 (11)0.0195 (10)0.0082 (10)0.0164 (10)
C10.0601 (17)0.0469 (15)0.0425 (15)0.0179 (13)0.0242 (13)0.0174 (12)
C20.078 (2)0.068 (2)0.0400 (16)0.0229 (17)0.0304 (15)0.0139 (15)
C30.0530 (17)0.085 (2)0.0401 (15)0.0222 (16)0.0197 (13)0.0332 (16)
C40.072 (2)0.074 (2)0.0598 (19)0.0351 (17)0.0300 (16)0.0444 (17)
C50.0697 (19)0.0548 (17)0.0465 (16)0.0294 (15)0.0276 (14)0.0250 (14)
C60.0390 (13)0.0440 (14)0.0338 (13)0.0130 (11)0.0125 (11)0.0152 (11)
C70.0436 (14)0.0380 (13)0.0335 (13)0.0161 (11)0.0141 (11)0.0145 (11)
C80.0369 (14)0.0538 (16)0.0412 (15)0.0043 (12)0.0051 (11)0.0162 (13)
C90.072 (2)0.0579 (19)0.0514 (18)0.0207 (16)0.0073 (16)0.0100 (15)
C100.084 (2)0.089 (3)0.0437 (18)0.030 (2)0.0124 (17)0.0036 (18)
C110.0484 (17)0.089 (2)0.0433 (17)0.0099 (16)0.0057 (13)0.0230 (17)
C120.063 (2)0.071 (2)0.0563 (19)0.0170 (16)0.0006 (16)0.0274 (17)
C130.0630 (19)0.065 (2)0.0436 (16)0.0204 (16)0.0060 (14)0.0150 (15)
C140.092 (3)0.157 (4)0.049 (2)0.023 (3)0.010 (2)0.045 (2)
C150.0410 (14)0.0450 (15)0.0379 (14)0.0121 (11)0.0099 (11)0.0170 (12)
C160.0426 (14)0.0406 (14)0.0316 (13)0.0105 (11)0.0047 (11)0.0096 (11)
C170.0677 (19)0.0589 (18)0.0537 (18)0.0351 (16)0.0129 (15)0.0218 (15)
C180.068 (2)0.142 (4)0.076 (3)0.058 (3)0.014 (2)0.039 (3)
C190.071 (2)0.069 (2)0.0400 (15)0.0228 (16)0.0125 (14)0.0283 (15)
C200.082 (3)0.127 (4)0.086 (3)0.004 (3)0.025 (2)0.060 (3)
Geometric parameters (Å, º) top
S1—O21.426 (2)C9—H90.9300
S1—O11.427 (2)C10—C111.369 (5)
S1—N11.606 (2)C10—H100.9300
S1—C81.766 (3)C11—C121.375 (5)
Cl1—C11.735 (3)C11—C141.513 (5)
Cl2—C31.743 (3)C12—C131.376 (4)
O3—C161.234 (3)C12—H120.9300
N1—C71.466 (3)C13—H130.9300
N1—H10.79 (3)C14—H14A0.9600
N2—C161.331 (3)C14—H14B0.9600
N2—C171.462 (3)C14—H14C0.9600
N2—C191.466 (3)C15—C161.509 (3)
C1—C61.383 (4)C15—H15A0.9700
C1—C21.384 (4)C15—H15B0.9700
C2—C31.360 (4)C17—C181.502 (5)
C2—H20.9300C17—H17A0.9700
C3—C41.360 (4)C17—H17B0.9700
C4—C51.381 (4)C18—H18A0.9600
C4—H40.9300C18—H18B0.9600
C5—C61.380 (4)C18—H18C0.9600
C5—H50.9300C19—C201.487 (5)
C6—C71.525 (3)C19—H19A0.9700
C7—C151.534 (4)C19—H19B0.9700
C7—H70.9800C20—H20A0.9600
C8—C91.369 (4)C20—H20B0.9600
C8—C131.377 (4)C20—H20C0.9600
C9—C101.378 (5)
O2—S1—O1120.48 (15)C12—C11—C14121.7 (3)
O2—S1—N1105.55 (14)C11—C12—C13121.6 (3)
O1—S1—N1107.42 (13)C11—C12—H12119.2
O2—S1—C8107.45 (13)C13—C12—H12119.2
O1—S1—C8107.80 (14)C12—C13—C8119.5 (3)
N1—S1—C8107.55 (12)C12—C13—H13120.3
C7—N1—S1122.90 (18)C8—C13—H13120.3
C7—N1—H1115 (2)C11—C14—H14A109.6
S1—N1—H1113 (2)C11—C14—H14B109.4
C16—N2—C17125.3 (2)H14A—C14—H14B109.5
C16—N2—C19117.9 (2)C11—C14—H14C109.4
C17—N2—C19116.8 (2)H14A—C14—H14C109.5
C6—C1—C2122.4 (3)H14B—C14—H14C109.5
C6—C1—Cl1120.1 (2)C16—C15—C7111.5 (2)
C2—C1—Cl1117.5 (2)C16—C15—H15A109.3
C3—C2—C1118.7 (3)C7—C15—H15A109.3
C3—C2—H2120.6C16—C15—H15B109.3
C1—C2—H2120.6C7—C15—H15B109.3
C2—C3—C4121.2 (3)H15A—C15—H15B108.0
C2—C3—Cl2118.9 (2)O3—C16—N2120.2 (2)
C4—C3—Cl2120.0 (2)O3—C16—C15119.6 (2)
C3—C4—C5119.2 (3)N2—C16—C15120.1 (2)
C3—C4—H4120.4N2—C17—C18112.7 (3)
C5—C4—H4120.4N2—C17—H17A109.1
C6—C5—C4122.0 (3)C18—C17—H17A109.1
C6—C5—H5119.0N2—C17—H17B109.1
C4—C5—H5119.0C18—C17—H17B109.1
C5—C6—C1116.4 (2)H17A—C17—H17B107.8
C5—C6—C7120.5 (2)C17—C18—H18A109.5
C1—C6—C7123.1 (2)C17—C18—H18B109.5
N1—C7—C6113.31 (19)H18A—C18—H18B109.5
N1—C7—C15108.5 (2)C17—C18—H18C109.5
C6—C7—C15110.5 (2)H18A—C18—H18C109.5
N1—C7—H7108.1H18B—C18—H18C109.5
C6—C7—H7108.1N2—C19—C20112.0 (3)
C15—C7—H7108.1N2—C19—H19A109.2
C9—C8—C13119.8 (3)C20—C19—H19A109.2
C9—C8—S1120.8 (2)N2—C19—H19B109.2
C13—C8—S1119.2 (2)C20—C19—H19B109.2
C8—C9—C10119.5 (3)H19A—C19—H19B107.9
C8—C9—H9120.2C19—C20—H20A109.5
C10—C9—H9120.2C19—C20—H20B109.5
C11—C10—C9121.8 (3)H20A—C20—H20B109.5
C11—C10—H10119.1C19—C20—H20C109.5
C9—C10—H10119.1H20A—C20—H20C109.5
C10—C11—C12117.8 (3)H20B—C20—H20C109.5
C10—C11—C14120.6 (3)
O2—S1—N1—C7172.46 (19)O2—S1—C8—C1337.9 (3)
O1—S1—N1—C742.7 (2)O1—S1—C8—C13169.1 (2)
C8—S1—N1—C773.0 (2)N1—S1—C8—C1375.3 (3)
C6—C1—C2—C30.1 (5)C13—C8—C9—C101.2 (5)
Cl1—C1—C2—C3179.9 (2)S1—C8—C9—C10174.3 (3)
C1—C2—C3—C42.0 (5)C8—C9—C10—C110.0 (5)
C1—C2—C3—Cl2178.3 (2)C9—C10—C11—C121.0 (5)
C2—C3—C4—C52.3 (5)C9—C10—C11—C14179.1 (3)
Cl2—C3—C4—C5178.1 (2)C10—C11—C12—C130.8 (5)
C3—C4—C5—C60.4 (5)C14—C11—C12—C13179.3 (3)
C4—C5—C6—C11.5 (4)C11—C12—C13—C80.4 (5)
C4—C5—C6—C7176.6 (3)C9—C8—C13—C121.4 (5)
C2—C1—C6—C51.8 (4)S1—C8—C13—C12174.1 (2)
Cl1—C1—C6—C5178.2 (2)N1—C7—C15—C1651.4 (3)
C2—C1—C6—C7176.3 (3)C6—C7—C15—C16176.2 (2)
Cl1—C1—C6—C73.7 (4)C17—N2—C16—O3174.7 (3)
S1—N1—C7—C673.7 (3)C19—N2—C16—O33.7 (4)
S1—N1—C7—C15163.18 (17)C17—N2—C16—C158.1 (4)
C5—C6—C7—N148.9 (3)C19—N2—C16—C15173.5 (2)
C1—C6—C7—N1129.2 (3)C7—C15—C16—O393.2 (3)
C5—C6—C7—C1573.2 (3)C7—C15—C16—N284.0 (3)
C1—C6—C7—C15108.8 (3)C16—N2—C17—C18100.1 (3)
O2—S1—C8—C9146.6 (3)C19—N2—C17—C1878.3 (4)
O1—S1—C8—C915.4 (3)C16—N2—C19—C2079.4 (4)
N1—S1—C8—C9100.2 (3)C17—N2—C19—C20102.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.79 (3)2.04 (3)2.806 (3)166 (3)
Symmetry code: (i) x+1, y+1, z+1.
 

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