In the title compound, C
17H
17ClN
2O
2S, the
o-chlorophenyl group is almost coplanar with the thiophene ring and the C—N bond distance indicates delocalization of π bonding across the ring systems. There are intramolecular N—H
O, N—H
Cl and C—H
O hydrogen bonds, and intermolecular C—H
O interactions.
Supporting information
CCDC reference: 263686
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.043
- wR factor = 0.127
- Data-to-parameter ratio = 14.0
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42
PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 - C5 .. 5.25 su
PLAT414_ALERT_2_C Short Intra D-H..H-X H2 .. H4B .. 1.97 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1
C17 H17 Cl N2 O2 S
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
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), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).
2-Acetamido-
N-(2-chlorophenyl)-4,5,6,7-tetrahydrobenzothiophene-3-carboxamide
top
Crystal data top
C17H17ClN2O2S | F(000) = 728 |
Mr = 348.84 | Dx = 1.439 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 450 reflections |
a = 8.2523 (7) Å | θ = 2.1–25.4° |
b = 19.6807 (16) Å | µ = 0.38 mm−1 |
c = 10.2857 (8) Å | T = 296 K |
β = 105.388 (1)° | Prism, colourless |
V = 1610.6 (2) Å3 | 0.43 × 0.19 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2948 independent reflections |
Radiation source: fine-focus sealed tube | 2597 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 25.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.920, Tmax = 0.956 | k = −23→23 |
11817 measured reflections | l = −12→12 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0719P)2 + 0.7245P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.007 |
2948 reflections | Δρmax = 0.60 e Å−3 |
210 parameters | Δρmin = −0.25 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: 0.0157 (19) |
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 | |
Cl1 | 1.23233 (9) | −0.08186 (4) | 0.16979 (6) | 0.0703 (2) | |
S1 | 1.05462 (7) | 0.16461 (3) | 0.63249 (6) | 0.0464 (2) | |
O1 | 1.1952 (2) | 0.16622 (9) | 0.90573 (18) | 0.0669 (5) | |
O2 | 1.3805 (2) | −0.02230 (8) | 0.67658 (15) | 0.0624 (5) | |
N1 | 1.2646 (2) | 0.07585 (9) | 0.79819 (17) | 0.0442 (4) | |
H1 | 1.3160 | 0.0374 | 0.8094 | 0.053* | |
N2 | 1.2843 (2) | −0.04001 (9) | 0.45311 (16) | 0.0435 (4) | |
H2 | 1.2174 | −0.0246 | 0.3802 | 0.052* | |
C1 | 1.2736 (3) | 0.11396 (11) | 0.9101 (2) | 0.0470 (5) | |
C2 | 1.1796 (2) | 0.09363 (10) | 0.6676 (2) | 0.0385 (4) | |
C3 | 1.1872 (2) | 0.05839 (10) | 0.55290 (19) | 0.0382 (4) | |
C4 | 1.0786 (3) | 0.07484 (13) | 0.2881 (2) | 0.0562 (6) | |
H4A | 1.0037 | 0.0363 | 0.2615 | 0.067* | |
H4B | 1.1887 | 0.0618 | 0.2796 | 0.067* | |
C5 | 1.0116 (4) | 0.13597 (18) | 0.1931 (3) | 0.0796 (9) | |
H5A | 1.1002 | 0.1695 | 0.2028 | 0.096* | |
H5B | 0.9812 | 0.1204 | 0.1003 | 0.096* | |
C6 | 0.8642 (4) | 0.16804 (16) | 0.2229 (3) | 0.0786 (9) | |
H6A | 0.8220 | 0.2036 | 0.1573 | 0.094* | |
H6B | 0.7761 | 0.1344 | 0.2143 | 0.094* | |
C7 | 0.9054 (3) | 0.19798 (13) | 0.3622 (3) | 0.0577 (6) | |
H7A | 0.8024 | 0.2071 | 0.3876 | 0.069* | |
H7B | 0.9646 | 0.2406 | 0.3633 | 0.069* | |
C8 | 1.0133 (3) | 0.14932 (11) | 0.4615 (2) | 0.0440 (5) | |
C9 | 1.0906 (2) | 0.09286 (11) | 0.4324 (2) | 0.0413 (5) | |
C10 | 1.2905 (2) | −0.00362 (10) | 0.56657 (19) | 0.0402 (4) | |
C11 | 1.3723 (3) | −0.09943 (10) | 0.4386 (2) | 0.0422 (5) | |
C12 | 1.4735 (3) | −0.13581 (11) | 0.5453 (2) | 0.0494 (5) | |
H12 | 1.4847 | −0.1213 | 0.6333 | 0.059* | |
C13 | 1.5579 (3) | −0.19363 (12) | 0.5222 (3) | 0.0581 (6) | |
H13 | 1.6258 | −0.2171 | 0.5950 | 0.070* | |
C14 | 1.5431 (3) | −0.21675 (12) | 0.3944 (3) | 0.0640 (7) | |
H14 | 1.6006 | −0.2555 | 0.3804 | 0.077* | |
C15 | 1.4423 (3) | −0.18208 (13) | 0.2863 (3) | 0.0620 (7) | |
H15 | 1.4309 | −0.1976 | 0.1990 | 0.074* | |
C16 | 1.3576 (3) | −0.12384 (11) | 0.3084 (2) | 0.0494 (5) | |
C17 | 1.3905 (4) | 0.08692 (14) | 1.0373 (2) | 0.0677 (7) | |
H17A | 1.5047 | 0.0950 | 1.0357 | 0.102* | |
H17B | 1.3727 | 0.0390 | 1.0437 | 0.102* | |
H17C | 1.3689 | 0.1095 | 1.1137 | 0.102* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0865 (5) | 0.0795 (5) | 0.0414 (3) | −0.0034 (4) | 0.0109 (3) | −0.0115 (3) |
S1 | 0.0440 (3) | 0.0426 (3) | 0.0527 (4) | 0.0029 (2) | 0.0132 (2) | −0.0004 (2) |
O1 | 0.0763 (12) | 0.0636 (11) | 0.0571 (10) | 0.0133 (9) | 0.0109 (9) | −0.0161 (8) |
O2 | 0.0826 (12) | 0.0568 (10) | 0.0376 (8) | 0.0248 (9) | −0.0018 (8) | −0.0034 (7) |
N1 | 0.0545 (10) | 0.0398 (9) | 0.0369 (9) | 0.0022 (8) | 0.0096 (8) | −0.0008 (7) |
N2 | 0.0454 (9) | 0.0468 (10) | 0.0354 (9) | 0.0040 (8) | 0.0059 (7) | −0.0019 (7) |
C1 | 0.0530 (12) | 0.0455 (12) | 0.0428 (11) | −0.0050 (10) | 0.0130 (9) | −0.0056 (9) |
C2 | 0.0385 (10) | 0.0374 (10) | 0.0397 (10) | −0.0044 (8) | 0.0104 (8) | 0.0001 (8) |
C3 | 0.0371 (10) | 0.0404 (10) | 0.0364 (10) | −0.0038 (8) | 0.0084 (8) | 0.0011 (8) |
C4 | 0.0570 (14) | 0.0687 (16) | 0.0391 (12) | 0.0057 (12) | 0.0061 (10) | 0.0048 (10) |
C5 | 0.088 (2) | 0.100 (2) | 0.0460 (14) | 0.0108 (18) | 0.0088 (13) | 0.0153 (14) |
C6 | 0.0726 (18) | 0.082 (2) | 0.0663 (18) | 0.0124 (15) | −0.0074 (14) | 0.0218 (15) |
C7 | 0.0455 (12) | 0.0578 (15) | 0.0665 (15) | 0.0054 (10) | 0.0089 (11) | 0.0194 (12) |
C8 | 0.0359 (10) | 0.0464 (11) | 0.0486 (12) | −0.0033 (9) | 0.0089 (9) | 0.0082 (9) |
C9 | 0.0350 (10) | 0.0482 (12) | 0.0391 (11) | −0.0043 (8) | 0.0068 (8) | 0.0043 (8) |
C10 | 0.0411 (10) | 0.0421 (11) | 0.0360 (10) | −0.0031 (8) | 0.0080 (8) | −0.0012 (8) |
C11 | 0.0399 (10) | 0.0410 (11) | 0.0484 (12) | −0.0088 (8) | 0.0167 (9) | −0.0067 (9) |
C12 | 0.0466 (12) | 0.0470 (12) | 0.0553 (13) | −0.0008 (9) | 0.0144 (10) | 0.0002 (10) |
C13 | 0.0520 (13) | 0.0456 (13) | 0.0798 (17) | −0.0012 (10) | 0.0229 (12) | 0.0040 (12) |
C14 | 0.0635 (15) | 0.0413 (13) | 0.097 (2) | −0.0038 (11) | 0.0383 (15) | −0.0081 (13) |
C15 | 0.0676 (16) | 0.0525 (14) | 0.0759 (17) | −0.0183 (12) | 0.0369 (14) | −0.0236 (13) |
C16 | 0.0498 (12) | 0.0496 (12) | 0.0517 (12) | −0.0137 (10) | 0.0182 (10) | −0.0100 (10) |
C17 | 0.090 (2) | 0.0681 (17) | 0.0399 (12) | 0.0086 (14) | 0.0083 (12) | −0.0060 (11) |
Geometric parameters (Å, º) top
Cl1—C16 | 1.733 (2) | C5—H5B | 0.9700 |
S1—C2 | 1.717 (2) | C6—C7 | 1.503 (4) |
S1—C8 | 1.726 (2) | C6—H6A | 0.9700 |
O1—C1 | 1.209 (3) | C6—H6B | 0.9700 |
O2—C10 | 1.233 (2) | C7—C8 | 1.507 (3) |
N1—C1 | 1.360 (3) | C7—H7A | 0.9700 |
N1—C2 | 1.385 (3) | C7—H7B | 0.9700 |
N1—H1 | 0.8600 | C8—C9 | 1.354 (3) |
N2—C10 | 1.359 (3) | C11—C12 | 1.389 (3) |
N2—C11 | 1.405 (3) | C11—C16 | 1.397 (3) |
N2—H2 | 0.8600 | C12—C13 | 1.388 (3) |
C1—C17 | 1.502 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.384 (3) | C13—C14 | 1.365 (4) |
C3—C9 | 1.452 (3) | C13—H13 | 0.9300 |
C3—C10 | 1.474 (3) | C14—C15 | 1.379 (4) |
C4—C9 | 1.503 (3) | C14—H14 | 0.9300 |
C4—C5 | 1.556 (4) | C15—C16 | 1.392 (3) |
C4—H4A | 0.9700 | C15—H15 | 0.9300 |
C4—H4B | 0.9700 | C17—H17A | 0.9600 |
C5—C6 | 1.473 (4) | C17—H17B | 0.9600 |
C5—H5A | 0.9700 | C17—H17C | 0.9600 |
| | | |
C2—S1—C8 | 91.02 (10) | C6—C7—H7B | 109.7 |
C1—N1—C2 | 125.57 (18) | C8—C7—H7B | 109.7 |
C1—N1—H1 | 117.2 | H7A—C7—H7B | 108.2 |
C2—N1—H1 | 117.2 | C9—C8—C7 | 126.8 (2) |
C10—N2—C11 | 128.86 (17) | C9—C8—S1 | 113.03 (16) |
C10—N2—H2 | 115.6 | C7—C8—S1 | 120.09 (17) |
C11—N2—H2 | 115.6 | C8—C9—C3 | 112.24 (19) |
O1—C1—N1 | 121.9 (2) | C8—C9—C4 | 120.05 (19) |
O1—C1—C17 | 123.2 (2) | C3—C9—C4 | 127.60 (19) |
N1—C1—C17 | 114.8 (2) | O2—C10—N2 | 120.48 (19) |
C3—C2—N1 | 125.04 (18) | O2—C10—C3 | 121.77 (18) |
C3—C2—S1 | 112.89 (15) | N2—C10—C3 | 117.75 (17) |
N1—C2—S1 | 122.06 (15) | C12—C11—C16 | 117.5 (2) |
C2—C3—C9 | 110.78 (18) | C12—C11—N2 | 124.32 (19) |
C2—C3—C10 | 119.31 (17) | C16—C11—N2 | 118.2 (2) |
C9—C3—C10 | 129.86 (18) | C11—C12—C13 | 120.7 (2) |
C9—C4—C5 | 110.9 (2) | C11—C12—H12 | 119.6 |
C9—C4—H4A | 109.5 | C13—C12—H12 | 119.6 |
C5—C4—H4A | 109.5 | C14—C13—C12 | 121.2 (2) |
C9—C4—H4B | 109.5 | C14—C13—H13 | 119.4 |
C5—C4—H4B | 109.5 | C12—C13—H13 | 119.4 |
H4A—C4—H4B | 108.0 | C13—C14—C15 | 119.4 (2) |
C6—C5—C4 | 112.1 (2) | C13—C14—H14 | 120.3 |
C6—C5—H5A | 109.2 | C15—C14—H14 | 120.3 |
C4—C5—H5A | 109.2 | C16—C15—C14 | 119.8 (2) |
C6—C5—H5B | 109.2 | C16—C15—H15 | 120.1 |
C4—C5—H5B | 109.2 | C14—C15—H15 | 120.1 |
H5A—C5—H5B | 107.9 | C15—C16—C11 | 121.3 (2) |
C7—C6—C5 | 112.1 (2) | C15—C16—Cl1 | 118.29 (19) |
C7—C6—H6A | 109.2 | C11—C16—Cl1 | 120.38 (18) |
C5—C6—H6A | 109.2 | C1—C17—H17A | 109.5 |
C7—C6—H6B | 109.2 | C1—C17—H17B | 109.5 |
C5—C6—H6B | 109.2 | H17A—C17—H17B | 109.5 |
H6A—C6—H6B | 107.9 | C1—C17—H17C | 109.5 |
C6—C7—C8 | 109.9 (2) | H17A—C17—H17C | 109.5 |
C6—C7—H7A | 109.7 | H17B—C17—H17C | 109.5 |
C8—C7—H7A | 109.7 | | |
| | | |
C2—N1—C1—O1 | 5.6 (3) | C2—C3—C9—C4 | 174.3 (2) |
C2—N1—C1—C17 | −173.0 (2) | C10—C3—C9—C4 | −3.1 (3) |
C1—N1—C2—C3 | 172.0 (2) | C5—C4—C9—C8 | 14.2 (3) |
C1—N1—C2—S1 | −6.7 (3) | C5—C4—C9—C3 | −161.7 (2) |
C8—S1—C2—C3 | −1.22 (16) | C11—N2—C10—O2 | −1.3 (3) |
C8—S1—C2—N1 | 177.64 (17) | C11—N2—C10—C3 | 178.49 (18) |
N1—C2—C3—C9 | −176.84 (17) | C2—C3—C10—O2 | −5.5 (3) |
S1—C2—C3—C9 | 2.0 (2) | C9—C3—C10—O2 | 171.7 (2) |
N1—C2—C3—C10 | 0.8 (3) | C2—C3—C10—N2 | 174.71 (18) |
S1—C2—C3—C10 | 179.67 (14) | C9—C3—C10—N2 | −8.1 (3) |
C9—C4—C5—C6 | −46.2 (3) | C10—N2—C11—C12 | 6.5 (3) |
C4—C5—C6—C7 | 63.0 (3) | C10—N2—C11—C16 | −173.56 (19) |
C5—C6—C7—C8 | −43.5 (3) | C16—C11—C12—C13 | 0.9 (3) |
C6—C7—C8—C9 | 11.7 (3) | N2—C11—C12—C13 | −179.18 (19) |
C6—C7—C8—S1 | −170.55 (18) | C11—C12—C13—C14 | −0.5 (3) |
C2—S1—C8—C9 | 0.08 (16) | C12—C13—C14—C15 | −0.1 (4) |
C2—S1—C8—C7 | −178.01 (18) | C13—C14—C15—C16 | 0.4 (4) |
C7—C8—C9—C3 | 178.96 (19) | C14—C15—C16—C11 | 0.0 (3) |
S1—C8—C9—C3 | 1.0 (2) | C14—C15—C16—Cl1 | 179.99 (18) |
C7—C8—C9—C4 | 2.4 (3) | C12—C11—C16—C15 | −0.6 (3) |
S1—C8—C9—C4 | −175.50 (16) | N2—C11—C16—C15 | 179.47 (19) |
C2—C3—C9—C8 | −1.9 (2) | C12—C11—C16—Cl1 | 179.40 (15) |
C10—C3—C9—C8 | −179.29 (19) | N2—C11—C16—Cl1 | −0.6 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2 | 0.86 | 1.98 | 2.616 (2) | 130 |
N2—H2···Cl1 | 0.86 | 2.47 | 2.948 (2) | 116 |
C7—H7B···O1i | 0.97 | 2.59 | 3.535 (3) | 163 |
C12—H12···O2 | 0.93 | 2.22 | 2.820 (3) | 121 |
Symmetry code: (i) x, −y+1/2, z−1/2. |