In the title compound, C
19H
19NO
3S, the thiophene ring is almost coplanar with the cinnamide moiety. An intramolecular N—H
O hydrogen bond forms a pseudo-six-membered ring, thus locking the molecular conformation and removing the conformational flexibility. In addition, the packing of molecules is stabilized by C—H
O interactions which form dimers.
Supporting information
CCDC reference: 239139
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.126
- Data-to-parameter ratio = 12.3
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low .... 0.92
PLAT391_ALERT_3_C Deviating Methyl C10 H-C-H Bond Angle ...... 101.00 Deg.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. O3 .. 2.62 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
0 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
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) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2003).
Methyl 2-{[(2E)-3-phenylprop-2-enoyl]amino}-
4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate
top
Crystal data top
C19H19NO3S | F(000) = 720 |
Mr = 341.42 | Dx = 1.310 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 575 reflections |
a = 9.811 (3) Å | θ = 1.5–21.5° |
b = 9.590 (3) Å | µ = 0.20 mm−1 |
c = 18.870 (5) Å | T = 293 K |
β = 102.893 (5)° | Prism, yellow |
V = 1730.7 (9) Å3 | 0.30 × 0.25 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3600 independent reflections |
Radiation source: fine-focus sealed tube | 2765 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 27.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→12 |
Tmin = 0.870, Tmax = 0.961 | k = −11→12 |
13095 measured reflections | l = −23→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | All H-atom parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0709P)2 + 0.2357P] where P = (Fo2 + 2Fc2)/3 |
3600 reflections | (Δ/σ)max = 0.001 |
293 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
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 | 0.65171 (5) | 0.16142 (5) | 0.90055 (3) | 0.06837 (19) | |
O1 | 0.81769 (16) | −0.16844 (13) | 1.06978 (7) | 0.0789 (4) | |
O2 | 0.64646 (16) | −0.30167 (13) | 1.00759 (7) | 0.0754 (4) | |
O3 | 0.87019 (15) | 0.30951 (15) | 0.98307 (9) | 0.0850 (5) | |
N1 | 0.85296 (15) | 0.08713 (17) | 1.01805 (8) | 0.0602 (4) | |
C1 | 0.73155 (16) | 0.05104 (18) | 0.96828 (8) | 0.0537 (4) | |
C2 | 0.66299 (16) | −0.07463 (17) | 0.96643 (8) | 0.0506 (4) | |
C3 | 0.54064 (16) | −0.07995 (17) | 0.90755 (8) | 0.0521 (4) | |
C4 | 0.52455 (17) | 0.0389 (2) | 0.86828 (9) | 0.0605 (4) | |
C5 | 0.4387 (2) | −0.1975 (2) | 0.88895 (11) | 0.0639 (5) | |
C6 | 0.3083 (2) | −0.1529 (3) | 0.83279 (12) | 0.0801 (6) | |
C7 | 0.3411 (2) | −0.0657 (3) | 0.77267 (11) | 0.0806 (6) | |
C8 | 0.4111 (2) | 0.0685 (3) | 0.80174 (12) | 0.0758 (6) | |
C9 | 0.71706 (19) | −0.18257 (18) | 1.01942 (9) | 0.0595 (4) | |
C10 | 0.6950 (5) | −0.4145 (3) | 1.05710 (19) | 0.1127 (11) | |
C11 | 0.91471 (18) | 0.2151 (2) | 1.02482 (10) | 0.0634 (4) | |
C12 | 1.03666 (18) | 0.2265 (2) | 1.08650 (10) | 0.0632 (4) | |
C13 | 1.10784 (18) | 0.3433 (2) | 1.10032 (10) | 0.0626 (4) | |
C14 | 1.23036 (16) | 0.36763 (19) | 1.15961 (9) | 0.0580 (4) | |
C15 | 1.2701 (2) | 0.2776 (3) | 1.21792 (11) | 0.0730 (5) | |
C16 | 1.3869 (2) | 0.3048 (3) | 1.27217 (11) | 0.0746 (6) | |
C17 | 1.4663 (2) | 0.4196 (2) | 1.26827 (10) | 0.0698 (5) | |
C18 | 1.4288 (2) | 0.5102 (2) | 1.21128 (11) | 0.0703 (5) | |
C19 | 1.31040 (19) | 0.4855 (2) | 1.15744 (11) | 0.0633 (5) | |
H1N | 0.881 (2) | 0.026 (2) | 1.0486 (11) | 0.065 (6)* | |
H5A | 0.4135 (19) | −0.230 (2) | 0.9314 (11) | 0.067 (5)* | |
H5B | 0.485 (2) | −0.276 (2) | 0.8709 (11) | 0.073 (6)* | |
H6A | 0.258 (3) | −0.232 (3) | 0.8172 (13) | 0.095 (7)* | |
H6B | 0.246 (3) | −0.099 (3) | 0.8578 (14) | 0.102 (8)* | |
H7A | 0.252 (2) | −0.046 (2) | 0.7371 (12) | 0.087 (6)* | |
H7B | 0.405 (3) | −0.125 (3) | 0.7486 (13) | 0.101 (7)* | |
H8A | 0.343 (3) | 0.131 (3) | 0.8145 (13) | 0.096 (7)* | |
H8B | 0.453 (2) | 0.115 (2) | 0.7661 (13) | 0.092 (7)* | |
H10A | 0.791 (3) | −0.437 (3) | 1.0592 (16) | 0.127 (12)* | |
H10B | 0.699 (4) | −0.391 (4) | 1.104 (2) | 0.160 (14)* | |
H10C | 0.640 (3) | −0.497 (3) | 1.0419 (16) | 0.130 (10)* | |
H12 | 1.064 (2) | 0.141 (2) | 1.1156 (11) | 0.076 (6)* | |
H13 | 1.0818 (19) | 0.418 (2) | 1.0697 (10) | 0.064 (5)* | |
H15 | 1.219 (2) | 0.199 (2) | 1.2233 (12) | 0.087 (7)* | |
H16 | 1.409 (2) | 0.245 (3) | 1.3087 (14) | 0.094 (7)* | |
H17 | 1.548 (2) | 0.435 (2) | 1.3038 (11) | 0.078 (6)* | |
H18 | 1.482 (2) | 0.591 (2) | 1.2049 (12) | 0.087 (7)* | |
H19 | 1.288 (2) | 0.542 (2) | 1.1202 (11) | 0.075 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0619 (3) | 0.0706 (3) | 0.0634 (3) | −0.0036 (2) | −0.0057 (2) | 0.0160 (2) |
O1 | 0.0954 (10) | 0.0691 (8) | 0.0547 (7) | 0.0050 (7) | −0.0203 (7) | 0.0022 (6) |
O2 | 0.0971 (10) | 0.0581 (8) | 0.0603 (8) | −0.0038 (7) | −0.0052 (7) | 0.0067 (6) |
O3 | 0.0728 (8) | 0.0760 (9) | 0.0880 (10) | −0.0115 (7) | −0.0207 (7) | 0.0185 (7) |
N1 | 0.0553 (8) | 0.0633 (9) | 0.0539 (8) | 0.0003 (7) | −0.0050 (6) | 0.0029 (7) |
C1 | 0.0499 (8) | 0.0632 (10) | 0.0444 (8) | 0.0054 (7) | 0.0030 (6) | −0.0010 (7) |
C2 | 0.0553 (8) | 0.0536 (9) | 0.0396 (7) | 0.0056 (7) | 0.0038 (6) | −0.0047 (6) |
C3 | 0.0512 (8) | 0.0594 (9) | 0.0427 (8) | 0.0058 (7) | 0.0040 (6) | −0.0072 (7) |
C4 | 0.0561 (9) | 0.0704 (11) | 0.0490 (9) | 0.0042 (8) | −0.0007 (7) | 0.0031 (8) |
C5 | 0.0657 (10) | 0.0645 (11) | 0.0558 (10) | −0.0020 (9) | 0.0012 (8) | −0.0130 (9) |
C6 | 0.0664 (12) | 0.0879 (15) | 0.0733 (13) | −0.0106 (11) | −0.0118 (10) | −0.0122 (12) |
C7 | 0.0678 (12) | 0.1070 (17) | 0.0552 (10) | 0.0138 (11) | −0.0113 (9) | −0.0130 (11) |
C8 | 0.0626 (11) | 0.0939 (16) | 0.0600 (11) | 0.0076 (11) | −0.0099 (9) | 0.0082 (11) |
C9 | 0.0722 (11) | 0.0591 (10) | 0.0424 (8) | 0.0058 (8) | 0.0022 (7) | −0.0053 (7) |
C10 | 0.158 (3) | 0.0750 (17) | 0.0858 (19) | −0.0048 (18) | −0.0151 (19) | 0.0228 (14) |
C11 | 0.0532 (9) | 0.0695 (11) | 0.0619 (10) | −0.0030 (8) | 0.0007 (8) | 0.0025 (9) |
C12 | 0.0539 (9) | 0.0718 (12) | 0.0576 (10) | −0.0029 (8) | −0.0006 (7) | 0.0041 (9) |
C13 | 0.0507 (9) | 0.0734 (12) | 0.0578 (10) | −0.0008 (8) | −0.0006 (7) | 0.0071 (9) |
C14 | 0.0473 (8) | 0.0712 (11) | 0.0521 (9) | 0.0003 (7) | 0.0042 (7) | −0.0003 (8) |
C15 | 0.0595 (10) | 0.0943 (15) | 0.0612 (11) | −0.0095 (10) | 0.0051 (8) | 0.0157 (10) |
C16 | 0.0641 (11) | 0.1053 (17) | 0.0498 (10) | 0.0092 (11) | 0.0028 (8) | 0.0121 (10) |
C17 | 0.0571 (10) | 0.0879 (14) | 0.0560 (10) | 0.0087 (10) | −0.0052 (8) | −0.0161 (10) |
C18 | 0.0624 (10) | 0.0663 (12) | 0.0738 (12) | −0.0022 (9) | −0.0028 (9) | −0.0144 (10) |
C19 | 0.0633 (10) | 0.0595 (10) | 0.0594 (10) | 0.0035 (8) | −0.0025 (8) | −0.0022 (9) |
Geometric parameters (Å, º) top
S1—C1 | 1.7090 (16) | C5—H5A | 0.94 (2) |
S1—C4 | 1.7229 (19) | C18—C17 | 1.367 (3) |
O2—C9 | 1.329 (2) | C18—C19 | 1.382 (2) |
O2—C10 | 1.440 (3) | C18—H18 | 0.95 (2) |
O1—C9 | 1.216 (2) | C7—C6 | 1.501 (3) |
O3—C11 | 1.216 (2) | C7—C8 | 1.504 (3) |
N1—C11 | 1.362 (2) | C7—H7B | 1.02 (3) |
N1—C1 | 1.386 (2) | C7—H7A | 0.99 (2) |
N1—H1N | 0.83 (2) | C17—C16 | 1.360 (3) |
C2—C1 | 1.377 (2) | C17—H17 | 0.93 (2) |
C2—C3 | 1.443 (2) | C19—H19 | 0.88 (2) |
C2—C9 | 1.455 (2) | C15—C16 | 1.380 (3) |
C3—C4 | 1.349 (2) | C15—H15 | 0.92 (2) |
C3—C5 | 1.496 (3) | C13—H13 | 0.92 (2) |
C4—C8 | 1.508 (2) | C16—H16 | 0.89 (3) |
C14—C19 | 1.382 (3) | C6—H6B | 0.99 (3) |
C14—C15 | 1.385 (3) | C6—H6A | 0.92 (3) |
C14—C13 | 1.467 (2) | C8—H8A | 0.97 (3) |
C12—C13 | 1.315 (3) | C8—H8B | 0.97 (2) |
C12—C11 | 1.475 (2) | C10—H10B | 0.91 (4) |
C12—H12 | 0.99 (2) | C10—H10C | 0.96 (3) |
C5—C6 | 1.529 (3) | C10—H10A | 0.96 (3) |
C5—H5B | 0.98 (2) | | |
| | | |
C1—S1—C4 | 90.96 (8) | C16—C17—H17 | 119.9 (13) |
C9—O2—C10 | 116.9 (2) | C18—C17—H17 | 120.1 (13) |
C11—N1—C1 | 125.84 (16) | O1—C9—O2 | 121.95 (16) |
C11—N1—H1N | 120.3 (14) | O1—C9—C2 | 124.48 (16) |
C1—N1—H1N | 113.4 (14) | O2—C9—C2 | 113.57 (14) |
C1—C2—C3 | 111.60 (14) | C14—C19—C18 | 120.53 (19) |
C1—C2—C9 | 120.29 (14) | C14—C19—H19 | 119.4 (14) |
C3—C2—C9 | 128.11 (15) | C18—C19—H19 | 119.9 (14) |
C2—C1—N1 | 125.23 (15) | C16—C15—C14 | 120.7 (2) |
C2—C1—S1 | 112.55 (11) | C16—C15—H15 | 117.1 (14) |
N1—C1—S1 | 122.22 (14) | C14—C15—H15 | 122.2 (15) |
C4—C3—C2 | 111.60 (15) | C12—C13—C14 | 126.55 (18) |
C4—C3—C5 | 121.17 (15) | C12—C13—H13 | 118.5 (12) |
C2—C3—C5 | 127.22 (15) | C14—C13—H13 | 115.0 (12) |
C3—C4—C8 | 126.19 (17) | C17—C16—C15 | 120.2 (2) |
C3—C4—S1 | 113.28 (12) | C17—C16—H16 | 121.5 (16) |
C8—C4—S1 | 120.53 (15) | C15—C16—H16 | 118.3 (16) |
C19—C14—C15 | 118.21 (17) | C7—C6—C5 | 113.11 (19) |
C19—C14—C13 | 118.81 (17) | C7—C6—H6B | 109.0 (15) |
C15—C14—C13 | 122.98 (18) | C5—C6—H6B | 108.8 (14) |
C13—C12—C11 | 121.39 (18) | C7—C6—H6A | 114.3 (15) |
C13—C12—H12 | 122.0 (12) | C5—C6—H6A | 107.4 (15) |
C11—C12—H12 | 116.5 (12) | H6B—C6—H6A | 104 (2) |
C3—C5—C6 | 111.34 (18) | C7—C8—C4 | 109.57 (18) |
C3—C5—H5B | 108.9 (12) | C7—C8—H8A | 109.6 (14) |
C6—C5—H5B | 110.7 (12) | C4—C8—H8A | 109.4 (14) |
C3—C5—H5A | 109.9 (12) | C7—C8—H8B | 111.8 (14) |
C6—C5—H5A | 110.2 (12) | C4—C8—H8B | 108.5 (14) |
H5B—C5—H5A | 105.7 (17) | H8A—C8—H8B | 108 (2) |
C17—C18—C19 | 120.3 (2) | O2—C10—H10B | 112 (2) |
C17—C18—H18 | 123.8 (13) | O2—C10—H10C | 109.9 (18) |
C19—C18—H18 | 115.9 (13) | H10B—C10—H10C | 114 (3) |
C6—C7—C8 | 111.00 (18) | O2—C10—H10A | 112 (2) |
C6—C7—H7B | 106.6 (14) | H10B—C10—H10A | 101 (3) |
C8—C7—H7B | 111.1 (14) | H10C—C10—H10A | 108 (3) |
C6—C7—H7A | 108.3 (13) | O3—C11—N1 | 121.49 (16) |
C8—C7—H7A | 110.0 (13) | O3—C11—C12 | 124.55 (18) |
H7B—C7—H7A | 109.7 (19) | N1—C11—C12 | 113.96 (16) |
C16—C17—C18 | 119.98 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C19—H19···O3i | 0.88 (2) | 2.62 (2) | 3.455 (2) | 159 (2) |
N1—H1N···O1 | 0.83 (2) | 2.03 (2) | 2.689 (2) | 136 (2) |
Symmetry code: (i) −x+2, −y+1, −z+2. |