Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The cyclo­hexene ring of the title compound, C17H17ClN2O2S, shows disorder, with a 60% major conformer and a 40% minor conformer. Both adopt half-chair conformations. In addition to intra­molecular N—H...N and C—H...O hydrogen bonds, there are inter­molecular N—H...O hydrogen bonds and very weak C—H...N and C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805020970/bh6009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805020970/bh6009Isup2.hkl
Contains datablock I

CCDC reference: 282231

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.055
  • wR factor = 0.138
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H1 .. N2 .. 2.64 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4
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 0 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 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-(Acetylamido)-N-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene- 3-carboxamide top
Crystal data top
C17H17ClN2O2SF(000) = 728
Mr = 348.84Dx = 1.340 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 540 reflections
a = 9.3999 (18) Åθ = 2.0–26.4°
b = 20.274 (4) ŵ = 0.35 mm1
c = 9.7668 (19) ÅT = 294 K
β = 111.764 (3)°Prism, colourless
V = 1728.6 (6) Å30.38 × 0.19 × 0.16 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
3206 independent reflections
Radiation source: fine-focus sealed tube2553 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
φ and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.925, Tmax = 0.946k = 2423
12791 measured reflectionsl = 1111
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0675P)2 + 0.6634P]
where P = (Fo2 + 2Fc2)/3
3206 reflections(Δ/σ)max = 0.003
243 parametersΔρmax = 0.34 e Å3
2 restraintsΔρmin = 0.32 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*/UeqOcc. (<1)
Cl10.52198 (13)0.30520 (5)1.17983 (13)0.0932 (4)
N10.8307 (2)0.04105 (11)1.0682 (2)0.0413 (5)
H10.77240.02051.10400.050*
N20.6256 (2)0.06350 (10)0.8925 (2)0.0405 (5)
H20.71410.06200.88570.049*
O11.0713 (2)0.07345 (10)1.1110 (2)0.0560 (5)
O20.39775 (19)0.00827 (9)0.8143 (2)0.0451 (5)
S10.83552 (8)0.13594 (4)0.87016 (8)0.0494 (2)
C10.9804 (3)0.04512 (13)1.1533 (3)0.0415 (6)
C20.7621 (3)0.06742 (13)0.9267 (3)0.0384 (6)
C30.6232 (3)0.04901 (13)0.8245 (3)0.0372 (6)
C40.4235 (4)0.08717 (18)0.5690 (3)0.0544 (8)
C70.6613 (5)0.1919 (2)0.5937 (4)0.0679 (10)
C80.6751 (3)0.14078 (14)0.7093 (3)0.0488 (7)
C90.5717 (3)0.09264 (13)0.6998 (3)0.0423 (6)
C100.5364 (3)0.00955 (13)0.8423 (3)0.0370 (6)
C110.5937 (3)0.12179 (13)0.9544 (3)0.0379 (6)
C120.7154 (3)0.15327 (15)1.0596 (3)0.0514 (7)
H120.81350.13601.08420.062*
C130.6956 (4)0.20920 (16)1.1285 (4)0.0586 (8)
H130.77870.22971.19980.070*
C140.5501 (4)0.23457 (14)1.0903 (3)0.0529 (7)
C150.4273 (3)0.20512 (14)0.9848 (3)0.0490 (7)
H150.32980.22300.95980.059*
C160.4485 (3)0.14855 (13)0.9153 (3)0.0428 (6)
H160.36560.12860.84260.051*
C171.0269 (4)0.01289 (17)1.3020 (3)0.0585 (8)
H17A1.09940.02161.30950.088*
H17B0.93810.00551.31410.088*
H17C1.07270.04511.37750.088*
C50.3962 (9)0.1488 (5)0.4710 (9)0.073 (2)0.59
H5A0.31940.13830.37510.087*0.59
H5B0.35460.18330.51400.087*0.59
C60.5331 (11)0.1747 (5)0.4496 (10)0.079 (3)0.59
H6A0.50490.21390.38830.095*0.59
H6B0.56970.14210.39790.095*0.59
C5'0.4350 (14)0.1238 (5)0.4392 (11)0.058 (3)0.41
H5A'0.33520.12640.36030.069*0.41
H5B'0.50450.10120.40250.069*0.41
C6'0.4949 (18)0.1933 (6)0.4919 (14)0.072 (4)0.41
H6A'0.48360.22070.40720.086*0.41
H6B'0.43420.21260.54320.086*0.41
H4A0.338 (4)0.0900 (16)0.602 (4)0.072 (10)*
H4B0.412 (4)0.043 (2)0.532 (4)0.089 (13)*
H7A0.677 (5)0.234 (2)0.636 (5)0.102 (15)*
H7B0.748 (4)0.1916 (17)0.566 (4)0.079 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0990 (8)0.0634 (6)0.1148 (9)0.0119 (5)0.0369 (7)0.0345 (5)
N10.0298 (11)0.0551 (14)0.0409 (12)0.0079 (10)0.0152 (10)0.0037 (10)
N20.0303 (11)0.0427 (13)0.0535 (13)0.0034 (9)0.0212 (10)0.0022 (10)
O10.0316 (10)0.0668 (14)0.0720 (14)0.0061 (9)0.0221 (10)0.0025 (11)
O20.0284 (10)0.0561 (12)0.0517 (11)0.0038 (8)0.0161 (8)0.0065 (9)
S10.0457 (4)0.0499 (4)0.0558 (5)0.0153 (3)0.0226 (3)0.0012 (3)
C10.0329 (14)0.0433 (15)0.0507 (16)0.0014 (11)0.0182 (12)0.0077 (12)
C20.0330 (14)0.0434 (15)0.0435 (15)0.0055 (11)0.0196 (12)0.0005 (12)
C30.0324 (13)0.0416 (14)0.0409 (14)0.0036 (11)0.0176 (11)0.0014 (11)
C40.0511 (19)0.061 (2)0.0470 (17)0.0016 (15)0.0129 (15)0.0014 (15)
C70.077 (3)0.061 (2)0.068 (2)0.0059 (19)0.030 (2)0.0192 (18)
C80.0528 (17)0.0465 (17)0.0517 (17)0.0022 (13)0.0247 (14)0.0059 (13)
C90.0430 (15)0.0444 (15)0.0433 (15)0.0007 (12)0.0204 (12)0.0017 (12)
C100.0346 (14)0.0460 (15)0.0339 (13)0.0045 (11)0.0166 (11)0.0018 (11)
C110.0358 (14)0.0377 (14)0.0440 (15)0.0034 (11)0.0195 (12)0.0050 (11)
C120.0364 (15)0.0536 (18)0.0627 (19)0.0043 (13)0.0165 (14)0.0022 (14)
C130.0498 (18)0.0553 (19)0.066 (2)0.0044 (14)0.0160 (16)0.0124 (16)
C140.0599 (19)0.0426 (16)0.0600 (18)0.0040 (14)0.0265 (15)0.0017 (14)
C150.0463 (17)0.0429 (16)0.0619 (18)0.0141 (13)0.0249 (15)0.0078 (14)
C160.0373 (14)0.0415 (15)0.0477 (16)0.0058 (12)0.0137 (12)0.0040 (12)
C170.0496 (18)0.068 (2)0.0511 (18)0.0008 (15)0.0111 (14)0.0023 (15)
C50.069 (5)0.089 (7)0.051 (5)0.011 (5)0.011 (3)0.018 (4)
C60.091 (6)0.098 (7)0.047 (5)0.011 (5)0.023 (4)0.022 (4)
C5'0.068 (7)0.059 (6)0.042 (5)0.013 (5)0.017 (4)0.002 (4)
C6'0.105 (10)0.065 (7)0.055 (7)0.015 (6)0.041 (6)0.020 (5)
Geometric parameters (Å, º) top
Cl1—C141.748 (3)C8—C91.356 (4)
N1—C11.345 (3)C11—C121.378 (4)
N1—C21.397 (3)C11—C161.384 (4)
N1—H10.8600C12—C131.366 (4)
N2—C101.355 (3)C12—H120.9300
N2—C111.409 (3)C13—C141.377 (4)
N2—H20.8600C13—H130.9300
O1—C11.221 (3)C14—C151.367 (4)
O2—C101.229 (3)C15—C161.384 (4)
S1—C21.730 (3)C15—H150.9300
S1—C81.730 (3)C16—H160.9300
C1—C171.503 (4)C17—H17A0.9600
C2—C31.369 (3)C17—H17B0.9600
C3—C91.436 (4)C17—H17C0.9600
C3—C101.487 (3)C5—C61.475 (10)
C4—C5'1.507 (11)C5—H5A0.9700
C4—C91.505 (4)C5—H5B0.9700
C4—C51.536 (9)C6—H6A0.9700
C4—H4A0.97 (4)C6—H6B0.9700
C4—H4B0.95 (4)C5'—C6'1.532 (14)
C7—C6'1.511 (16)C5'—H5A'0.9700
C7—C81.502 (4)C5'—H5B'0.9700
C7—C61.515 (10)C6'—H6A'0.9700
C7—H7A0.95 (4)C6'—H6B'0.9700
C7—H7B0.95 (4)
C1—N1—C2125.5 (2)C11—C12—C13121.6 (3)
C1—N1—H1117.2C11—C12—H12119.2
C2—N1—H1117.2C13—C12—H12119.2
C10—N2—C11129.1 (2)C14—C13—C12118.7 (3)
C10—N2—H2115.4C14—C13—H13120.7
C11—N2—H2115.4C12—C13—H13120.7
C2—S1—C891.08 (13)C13—C14—C15121.1 (3)
O1—C1—N1121.5 (3)C13—C14—Cl1119.3 (2)
O1—C1—C17122.9 (2)C15—C14—Cl1119.5 (2)
N1—C1—C17115.6 (2)C14—C15—C16119.8 (3)
C3—C2—N1125.7 (2)C14—C15—H15120.1
C3—C2—S1111.83 (19)C16—C15—H15120.1
N1—C2—S1122.03 (19)C11—C16—C15119.7 (3)
C2—C3—C9112.4 (2)C11—C16—H16120.1
C2—C3—C10123.3 (2)C15—C16—H16120.1
C9—C3—C10124.4 (2)C1—C17—H17A109.5
C5'—C4—C9110.2 (5)C1—C17—H17B109.5
C9—C4—C5111.0 (4)H17A—C17—H17B109.5
C5'—C4—H4A125 (2)C1—C17—H17C109.5
C9—C4—H4A110 (2)H17A—C17—H17C109.5
C5—C4—H4A101 (2)H17B—C17—H17C109.5
C5'—C4—H4B100 (2)C6—C5—C4115.1 (7)
C9—C4—H4B109 (2)C6—C5—H5A108.5
C5—C4—H4B124 (2)C4—C5—H5A108.5
H4A—C4—H4B101 (3)C6—C5—H5B108.5
C6'—C7—C8106.7 (6)C4—C5—H5B108.5
C8—C7—C6110.9 (4)H5A—C5—H5B107.5
C6'—C7—H7A103 (3)C5—C6—C7112.7 (7)
C8—C7—H7A110 (3)C5—C6—H6A109.1
C6—C7—H7A124 (3)C7—C6—H6A109.1
C6'—C7—H7B127 (2)C5—C6—H6B109.1
C8—C7—H7B112 (2)C7—C6—H6B109.1
C6—C7—H7B102 (2)H6A—C6—H6B107.8
H7A—C7—H7B97 (3)C4—C5'—C6'107.6 (8)
C9—C8—C7125.8 (3)C4—C5'—H5A'110.2
C9—C8—S1112.5 (2)C6'—C5'—H5A'110.2
C7—C8—S1121.7 (2)C4—C5'—H5B'110.2
C8—C9—C3112.2 (2)C6'—C5'—H5B'110.2
C8—C9—C4121.7 (3)H5A'—C5'—H5B'108.5
C3—C9—C4126.1 (2)C7—C6'—C5'111.5 (9)
O2—C10—N2124.1 (2)C7—C6'—H6A'109.3
O2—C10—C3122.7 (2)C5'—C6'—H6A'109.3
N2—C10—C3113.3 (2)C7—C6'—H6B'109.3
C12—C11—C16119.0 (2)C5'—C6'—H6B'109.3
C12—C11—N2117.3 (2)H6A'—C6'—H6B'108.0
C16—C11—N2123.7 (2)
C2—N1—C1—O10.0 (4)C11—N2—C10—O216.1 (4)
C2—N1—C1—C17179.8 (2)C11—N2—C10—C3163.7 (2)
C1—N1—C2—C3160.9 (3)C2—C3—C10—O2136.1 (3)
C1—N1—C2—S127.8 (4)C9—C3—C10—O243.8 (4)
C8—S1—C2—C31.3 (2)C2—C3—C10—N243.7 (3)
C8—S1—C2—N1171.1 (2)C9—C3—C10—N2136.5 (2)
N1—C2—C3—C9169.9 (2)C10—N2—C11—C12148.2 (3)
S1—C2—C3—C92.2 (3)C10—N2—C11—C1631.9 (4)
N1—C2—C3—C1010.0 (4)C16—C11—C12—C131.7 (4)
S1—C2—C3—C10177.97 (19)N2—C11—C12—C13178.4 (3)
C6'—C7—C8—C917.6 (6)C11—C12—C13—C140.5 (5)
C6—C7—C8—C912.1 (7)C12—C13—C14—C150.6 (5)
C6'—C7—C8—S1165.3 (5)C12—C13—C14—Cl1178.8 (2)
C6—C7—C8—S1165.0 (5)C13—C14—C15—C160.4 (4)
C2—S1—C8—C90.0 (2)Cl1—C14—C15—C16178.9 (2)
C2—S1—C8—C7177.5 (3)C12—C11—C16—C151.8 (4)
C7—C8—C9—C3176.1 (3)N2—C11—C16—C15178.3 (2)
S1—C8—C9—C31.2 (3)C14—C15—C16—C110.8 (4)
C7—C8—C9—C42.6 (5)C5'—C4—C5—C653.2 (12)
S1—C8—C9—C4179.9 (2)C9—C4—C5—C640.8 (9)
C2—C3—C9—C82.2 (3)C4—C5—C6—C757.5 (12)
C10—C3—C9—C8178.0 (2)C6'—C7—C6—C545.8 (11)
C2—C3—C9—C4179.2 (3)C8—C7—C6—C540.7 (10)
C10—C3—C9—C40.6 (4)C9—C4—C5'—C6'50.7 (10)
C5'—C4—C9—C819.7 (5)C5—C4—C5'—C6'46.3 (11)
C5—C4—C9—C810.9 (5)C8—C7—C6'—C5'50.5 (10)
C5'—C4—C9—C3158.8 (4)C6—C7—C6'—C5'52.8 (12)
C5—C4—C9—C3170.6 (4)C4—C5'—C6'—C770.6 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···N20.862.642.950 (2)103
C16—H16···O20.932.492.990 (3)114
N1—H1···O2i0.862.052.863 (3)158
N2—H2···O1ii0.862.022.869 (3)170
Symmetry codes: (i) x+1, y, z+2; (ii) x+2, y, z+2.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds