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An E configuration is found about the C=C double bond in the title mol­ecule, C18H19NO3S. Evidence is found for significant conjugation in the C6H4-NMe2 residue.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805034422/tk6266sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805034422/tk6266Isup2.hkl
Contains datablock I

CCDC reference: 289902

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.051
  • wR factor = 0.104
  • Data-to-parameter ratio = 16.5

checkCIF/PLATON results

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Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C6 ... 1.37 Ang. PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C10 ... 1.38 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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

Computing details top

Data collection: PROCESS-AUTO (Rigaku Corporation, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4-[4-(Dimethylamino)phenyl]-1-phenylsulfonylbut-3-en-2-one top
Crystal data top
C18H19NO3SF(000) = 696
Mr = 329.41Dx = 1.308 Mg m3
Monoclinic, P21/nMelting point: 157 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71075 Å
a = 7.224 (2) ÅCell parameters from 11803 reflections
b = 19.712 (6) Åθ = 3.1–27.5°
c = 12.177 (5) ŵ = 0.21 mm1
β = 105.272 (14)°T = 296 K
V = 1672.7 (10) Å3Block, yellow
Z = 40.35 × 0.18 × 0.16 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2183 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1Rint = 0.034
ω scansθmax = 27.5°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 99
Tmin = 0.960, Tmax = 0.967k = 2525
15968 measured reflectionsl = 1515
3834 independent reflections
Refinement top
Refinement on F2 w = 1/[0.0001 Fo2 + 3σ(Fo2) + 0.5]/(4Fo2)
R[F2 > 2σ(F2)] = 0.051(Δ/σ)max = 0.002
wR(F2) = 0.104Δρmax = 0.39 e Å3
S = 1.01Δρmin = 0.48 e Å3
3834 reflectionsExtinction correction: (Larson, 1970)
233 parametersExtinction coefficient: 283 (29)
H atoms treated by a mixture of independent and constrained refinement
Special details top

Geometry. The geometry of the title compound is linear.

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.69928 (8)0.73854 (3)0.51017 (5)0.06109 (17)
O10.49945 (18)0.75215 (6)0.46384 (12)0.0688 (4)
O20.8166 (2)0.79161 (8)0.57297 (13)0.0859 (5)
O30.5873 (3)0.58501 (11)0.4679 (2)0.1391 (10)
N10.2433 (2)0.52054 (11)0.8601 (2)0.0863 (7)
C10.7217 (3)0.66817 (12)0.6028 (2)0.0829 (8)
C20.5802 (4)0.61366 (16)0.5524 (3)0.1001 (12)
C50.1924 (3)0.56883 (17)0.7069 (2)0.0991 (12)
C60.1680 (3)0.60453 (12)0.7985 (2)0.0890 (9)
C70.0277 (3)0.58852 (12)0.8492 (2)0.0766 (8)
C80.0994 (3)0.53487 (11)0.8108 (2)0.0684 (7)
C90.0715 (4)0.49784 (12)0.7185 (2)0.0852 (9)
C100.0728 (5)0.51408 (17)0.6692 (2)0.1025 (11)
C110.2732 (3)0.56072 (14)0.9522 (2)0.1065 (11)
C120.3664 (3)0.46175 (13)0.8262 (2)0.1109 (11)
C130.7997 (2)0.71348 (9)0.39988 (18)0.0521 (5)
C140.9966 (2)0.71161 (12)0.4187 (2)0.0746 (7)
C151.0734 (3)0.69366 (12)0.3304 (2)0.0858 (9)
C160.9557 (3)0.67883 (12)0.2256 (2)0.0762 (8)
C170.7606 (3)0.68073 (12)0.2072 (2)0.0727 (7)
C180.6817 (2)0.69792 (10)0.29441 (19)0.0608 (6)
C310.4563 (7)0.6192 (2)0.6359 (4)0.089 (2)0.50
C320.4117 (6)0.5776 (2)0.5793 (4)0.080 (2)0.50
C410.3166 (6)0.5690 (2)0.6238 (4)0.075 (2)0.50
C420.3610 (6)0.6022 (2)0.6746 (4)0.072 (2)0.50
H40.323 (4)0.5379 (15)0.558 (2)0.141 (11)*
H30.430 (3)0.6351 (11)0.6976 (19)0.060 (7)*
H60.25430.64260.82750.108*
H70.01490.61480.91510.092*
H90.15680.45950.69000.101*
H100.08980.48640.60580.126*
H110.70350.68330.67500.100*
H120.84950.64940.61470.100*
H141.07970.72230.49430.087*
H151.21300.69210.34290.104*
H161.01160.66630.16340.095*
H170.67700.67020.13170.086*
H180.54220.69920.28270.072*
H1110.40480.55780.95440.132*
H1120.19170.54451.02280.132*
H1130.24190.60710.94080.132*
H1210.49220.47100.83490.133*
H1220.31200.42380.87310.133*
H1230.37520.45130.74800.133*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0574 (3)0.0656 (3)0.0562 (3)0.0066 (2)0.0077 (2)0.0034 (2)
O10.0539 (8)0.0769 (10)0.0736 (11)0.0150 (6)0.0130 (7)0.0026 (7)
O20.0797 (10)0.0896 (11)0.0793 (12)0.0059 (8)0.0050 (9)0.0299 (9)
O30.192 (2)0.0799 (14)0.152 (2)0.0321 (14)0.057 (2)0.0066 (14)
N10.0935 (15)0.0877 (14)0.0818 (16)0.0164 (11)0.0303 (12)0.0046 (12)
C10.0937 (17)0.0958 (18)0.0612 (17)0.0215 (15)0.0237 (14)0.0174 (14)
C20.104 (2)0.093 (2)0.113 (2)0.0162 (19)0.045 (2)0.048 (2)
C50.088 (2)0.105 (2)0.116 (2)0.0341 (18)0.047 (2)0.056 (2)
C60.0849 (18)0.0748 (17)0.110 (2)0.0078 (13)0.0309 (17)0.0201 (16)
C70.0809 (16)0.0728 (15)0.0775 (19)0.0024 (12)0.0235 (14)0.0019 (13)
C80.0798 (15)0.0591 (13)0.0631 (16)0.0053 (11)0.0134 (13)0.0052 (11)
C90.115 (2)0.0653 (15)0.0729 (18)0.0065 (13)0.0200 (16)0.0010 (13)
C100.141 (2)0.104 (2)0.072 (2)0.048 (2)0.0423 (19)0.0152 (17)
C110.106 (2)0.128 (2)0.095 (2)0.0037 (17)0.0439 (19)0.0025 (19)
C120.103 (2)0.092 (2)0.137 (3)0.0195 (16)0.0285 (19)0.0139 (19)
C130.0447 (10)0.0527 (11)0.0550 (13)0.0006 (8)0.0060 (9)0.0019 (9)
C140.0493 (12)0.0900 (17)0.0771 (18)0.0056 (10)0.0038 (12)0.0167 (13)
C150.0507 (12)0.0983 (18)0.112 (2)0.0055 (12)0.0283 (15)0.0145 (17)
C160.0812 (16)0.0766 (16)0.081 (2)0.0006 (13)0.0390 (15)0.0024 (13)
C170.0728 (15)0.0879 (16)0.0547 (16)0.0073 (12)0.0122 (12)0.0061 (12)
C180.0501 (11)0.0730 (14)0.0563 (14)0.0024 (9)0.0088 (11)0.0000 (11)
C310.094 (4)0.079 (4)0.086 (5)0.008 (3)0.009 (4)0.013 (4)
C320.105 (4)0.062 (3)0.076 (4)0.005 (3)0.031 (3)0.011 (2)
C410.112 (4)0.063 (3)0.050 (3)0.026 (3)0.022 (3)0.001 (2)
C420.100 (4)0.048 (3)0.053 (3)0.024 (3)0.007 (3)0.020 (2)
Geometric parameters (Å, º) top
S1—O11.4301 (13)C17—C181.374 (3)
S1—O21.4339 (16)C31—C411.393 (7)
S1—C11.768 (2)C32—C421.393 (7)
S1—C131.757 (2)C1—H110.970
O3—C21.186 (4)C1—H120.970
N1—C81.359 (3)C31—H30.88 (2)
N1—C111.435 (4)C42—H30.82 (2)
N1—C121.453 (3)C32—H41.00 (2)
C1—C21.498 (3)C41—H41.02 (2)
C2—C311.526 (7)C6—H60.980
C2—C321.519 (6)C7—H70.980
C5—C61.369 (4)C9—H90.980
C5—C101.383 (4)C10—H100.980
C5—C411.518 (6)C11—H1110.960
C5—C421.524 (5)C11—H1120.960
C6—C71.355 (4)C11—H1130.960
C7—C81.398 (3)C12—H1210.960
C8—C91.398 (3)C12—H1220.960
C9—C101.371 (5)C12—H1230.960
C13—C141.381 (2)C14—H140.980
C13—C181.376 (2)C15—H150.980
C14—C151.379 (4)C16—H160.980
C15—C161.366 (3)C17—H170.980
C16—C171.368 (3)C18—H180.980
O1···C73.465 (2)H3···H112.272
O1···C153.287 (2)H3···H123.447
O1···C163.555 (3)H3···H143.491
O2···C123.557 (3)H3···H1113.400
O2···C173.239 (2)H3···H1133.316
O2···C183.244 (2)H6···S13.326
O3···C323.257 (5)H6···O13.473
O3···C413.371 (5)H6···O23.180
N1···C313.580 (5)H6···C132.963
N1···C423.530 (4)H6···C143.396
C1···C73.586 (3)H6···C183.195
C2···C93.599 (3)H6···H32.280
C7···O13.465 (2)H6···H123.360
C7···C13.586 (3)H6···H183.453
C9···C23.599 (3)H6···H1113.040
C12···O23.557 (3)H7···S13.265
C12···C413.580 (5)H7···O12.698
C15···O13.287 (2)H7···O23.105
C16···O13.555 (3)H7···H113.460
C17···O23.239 (2)H7···H163.195
C18···O23.244 (2)H7···H1123.399
C31···N13.580 (5)H7···H1222.986
C32···O33.257 (5)H9···O33.315
C41···O33.371 (5)H9···C153.100
C41···C123.580 (5)H9···C163.132
C42···N13.530 (4)H9···C323.391
S1···H63.326H9···H42.946
S1···H73.265H9···H153.027
S1···H163.189H9···H163.073
O1···H63.473H10···O33.055
O1···H72.698H10···C103.244
O1···H143.205H10···H42.172
O1···H152.499H10···H43.159
O1···H162.895H10···H102.617
O1···H1133.250H10···H1213.544
O2···H63.180H11···C73.295
O2···H73.105H11···C83.475
O2···H153.573H11···C153.359
O2···H162.834H11···C163.399
O2···H172.621H11···H32.272
O2···H182.650H11···H73.460
O2···H1222.690H11···H153.185
O3···H42.61 (3)H11···H163.260
O3···H42.55 (3)H11···H183.374
O3···H33.43 (2)H11···H1133.495
O3···H93.315H12···C52.907
O3···H103.055H12···C62.894
O3···H153.452H12···C73.052
O3···H1232.766H12···C83.236
N1···H33.48 (2)H12···C93.235
N1···H1123.346H12···C103.097
C1···H32.73 (2)H12···H33.447
C2···H42.40 (3)H12···H63.360
C2···H43.42 (3)H14···O13.205
C2···H32.34 (2)H14···C173.210
C2···H153.517H14···C313.469
C5···H42.33 (3)H14···C423.493
C5···H32.18 (2)H14···H33.491
C5···H122.907H14···H172.677
C5···H1213.077H15···O12.499
C6···H32.59 (2)H15···O23.573
C6···H122.894H15···O33.452
C6···H1113.300H15···C23.517
C6···H1213.546H15···C183.589
C7···H113.295H15···H93.027
C7···H123.052H15···H113.185
C7···H1123.121H15···H182.670
C7···H1223.472H15···H1233.358
C8···H113.475H16···S13.189
C8···H123.236H16···O12.895
C8···H1122.955H16···O22.834
C9···H43.46 (3)H16···C93.521
C9···H123.235H16···C113.520
C9···H163.521H16···C123.575
C9···H1123.329H16···H73.195
C10···H42.57 (3)H16···H93.073
C10···H43.57 (2)H16···H113.260
C10···H33.46 (2)H16···H1123.086
C10···H103.244H16···H1133.073
C10···H123.097H16···H1222.927
C10···H1213.366H16···H1233.456
C11···H33.59 (2)H17···O22.621
C11···H163.520H17···C113.160
C11···H173.160H17···C123.560
C11···H1213.507H17···C143.474
C12···H163.575H17···H142.677
C12···H173.560H17···H1113.042
C12···H183.543H17···H1123.076
C12···H1113.514H17···H1132.831
C13···H62.963H17···H1213.160
C14···H63.396H17···H1223.211
C14···H173.474H18···O22.650
C15···H93.100H18···C123.543
C15···H113.359H18···C153.586
C15···H183.586H18···H63.453
C16···H93.132H18···H113.374
C16···H113.399H18···H152.670
C16···H1123.585H18···H1223.253
C17···H143.210H18···H1233.188
C17···H1123.575H111···C63.300
C17···H1133.549H111···C123.514
C17···H1213.528H111···C423.492
C18···H63.195H111···H33.400
C18···H153.589H111···H63.040
C31···H41.98 (2)H111···H173.042
C31···H30.88 (2)H111···H1113.021
C31···H143.469H111···H1212.909
C32···H41.00 (2)H111···H1223.316
C32···H31.81 (2)H112···N13.346
C32···H93.391H112···C73.121
C32···H1233.335H112···C82.955
C41···H41.02 (3)H112···C93.329
C41···H31.67 (2)H112···C163.585
C41···H1213.222H112···C173.575
C41···H1233.294H112···H73.399
C42···H41.87 (3)H112···H163.086
C42···H30.82 (2)H112···H173.076
C42···H143.493H112···H1123.445
C42···H1113.492H112···H1213.224
C42···H1213.245H112···H1223.578
C42···H1233.518H113···O13.250
H4···O32.61 (3)H113···C173.549
H4···O32.55 (3)H113···H33.316
H4···C22.40 (3)H113···H113.495
H4···C23.42 (3)H113···H163.073
H4···C52.33 (3)H113···H172.831
H4···C93.46 (3)H121···C53.077
H4···C102.57 (3)H121···C63.546
H4···C103.57 (2)H121···C103.366
H4···C311.98 (2)H121···C113.507
H4···C321.00 (2)H121···C173.528
H4···C411.02 (3)H121···C413.222
H4···C421.87 (3)H121···C423.245
H4···H43.56 (4)H121···H43.535
H4···H32.54 (3)H121···H103.544
H4···H92.946H121···H173.160
H4···H102.172H121···H1112.909
H4···H103.159H121···H1123.224
H4···H1213.535H122···O22.690
H4···H1233.216H122···C73.472
H3···O33.43 (2)H122···H72.986
H3···N13.48 (2)H122···H162.927
H3···C12.73 (2)H122···H173.211
H3···C22.34 (2)H122···H183.253
H3···C52.18 (2)H122···H1113.316
H3···C62.59 (2)H122···H1123.578
H3···C103.46 (2)H123···O32.766
H3···C113.59 (2)H123···C323.335
H3···C310.88 (2)H123···C413.294
H3···C321.81 (2)H123···C423.518
H3···C411.67 (2)H123···H43.216
H3···C420.82 (2)H123···H153.358
H3···H42.54 (3)H123···H163.456
H3···H62.280H123···H183.188
O1—S1—O2117.84 (9)C2—C1—H11110.6
O1—S1—C1108.18 (10)C2—C1—H12107.9
O1—S1—C13109.16 (9)H11—C1—H12109.5
O2—S1—C1106.88 (10)C5—C6—H6118.7
O2—S1—C13107.92 (10)C7—C6—H6119.7
C1—S1—C13106.27 (11)C6—C7—H7119.5
C8—N1—C11121.3 (2)C8—C7—H7118.6
C8—N1—C12121.5 (2)C8—C9—H9118.5
C11—N1—C12117.1 (2)C10—C9—H9120.3
S1—C1—C2111.31 (18)C5—C10—H10119.9
O3—C2—C1121.1 (3)C9—C10—H10118.9
O3—C2—C31141.2 (3)N1—C11—H111110.0
O3—C2—C32100.6 (3)N1—C11—H112109.5
C1—C2—C3197.6 (3)N1—C11—H113108.9
C1—C2—C32138.2 (3)H111—C11—H112109.5
C6—C5—C10117.9 (3)H111—C11—H113109.5
C6—C5—C41140.1 (3)H112—C11—H113109.5
C6—C5—C42105.8 (2)N1—C12—H121110.1
C10—C5—C41102.0 (3)N1—C12—H122109.2
C10—C5—C42136.3 (3)N1—C12—H123109.2
C5—C6—C7121.6 (2)H121—C12—H122109.5
C6—C7—C8121.9 (2)H121—C12—H123109.5
N1—C8—C7121.4 (2)H122—C12—H123109.5
N1—C8—C9122.4 (2)C13—C14—H14119.9
C7—C8—C9116.2 (2)C15—C14—H14121.0
C8—C9—C10121.2 (2)C14—C15—H15119.7
C5—C10—C9121.2 (3)C16—C15—H15120.0
S1—C13—C14119.72 (16)C15—C16—H16119.6
S1—C13—C18119.82 (15)C17—C16—H16119.8
C14—C13—C18120.4 (2)C16—C17—H17120.1
C13—C14—C15119.1 (2)C18—C17—H17119.9
C14—C15—C16120.3 (2)C13—C18—H18119.3
C15—C16—C17120.5 (2)C17—C18—H18120.9
C16—C17—C18120.0 (2)C2—C31—H3153.0 (16)
C13—C18—C17119.71 (19)C41—C31—H391.7 (15)
C2—C31—C41114.5 (4)C2—C32—H4144.0 (19)
C2—C32—C42114.8 (3)C42—C32—H4101.0 (19)
C5—C41—C31118.1 (4)C5—C41—H4132.7 (19)
C5—C42—C32117.9 (3)C31—C41—H4109.2 (19)
S1—C1—H11109.0C5—C42—H3135.2 (19)
S1—C1—H12108.6C32—C42—H3106.7 (18)
O1—S1—C1—C242.8 (2)C41—C5—C6—C7177.2 (3)
O1—S1—C13—C14166.20 (16)C6—C5—C42—C32177.0 (3)
O1—S1—C13—C1811.76 (18)C42—C5—C6—C7179.6 (2)
O2—S1—C1—C2170.7 (2)C10—C5—C41—C31179.5 (3)
O2—S1—C13—C1437.00 (19)C41—C5—C10—C9176.6 (2)
O2—S1—C13—C18140.96 (15)C10—C5—C42—C325.1 (6)
C1—S1—C13—C1477.35 (19)C42—C5—C10—C9179.3 (3)
C1—S1—C13—C18104.69 (17)C5—C6—C7—C80.0 (3)
C13—S1—C1—C274.3 (2)C6—C7—C8—N1178.0 (2)
C11—N1—C8—C71.2 (3)C6—C7—C8—C91.1 (3)
C11—N1—C8—C9177.8 (2)N1—C8—C9—C10178.9 (2)
C12—N1—C8—C7175.2 (2)C7—C8—C9—C100.2 (3)
C12—N1—C8—C95.7 (3)C8—C9—C10—C51.8 (4)
S1—C1—C2—O364.0 (3)S1—C13—C14—C15178.22 (18)
S1—C1—C2—C31112.3 (2)S1—C13—C18—C17177.64 (16)
S1—C1—C2—C32117.9 (4)C14—C13—C18—C170.3 (3)
O3—C2—C31—C4112.3 (7)C18—C13—C14—C150.3 (3)
O3—C2—C32—C42177.7 (3)C13—C14—C15—C160.9 (3)
C1—C2—C31—C41172.8 (3)C14—C15—C16—C170.9 (3)
C1—C2—C32—C423.9 (6)C15—C16—C17—C180.3 (3)
C6—C5—C10—C93.0 (4)C16—C17—C18—C130.3 (3)
C10—C5—C6—C72.0 (4)C2—C31—C41—C5177.4 (3)
C6—C5—C41—C310.1 (5)C2—C32—C42—C5179.7 (3)
 

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