In the structure of the title compound, C
12H
17NO
2S, the terminal ester group lies in the plane of the thiophene ring system. The cycloheptene ring adopts a half-chair conformation. There are intramolecular N—H
O and C—H
O interactions, and intermolecular N—H
O and C—H
π interactions.
Supporting information
CCDC reference: 274597
Key indicators
- Single-crystal X-ray study
- T = 290 K
- Mean (C-C) = 0.002 Å
- R factor = 0.038
- wR factor = 0.102
- Data-to-parameter ratio = 11.7
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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).
Ethyl
2-amino-5,6,7,8-tetrahydro-4
H-cyclohepta[
b]thiophene-3-carboxylate
top
Crystal data top
C12H17NO2S | F(000) = 512 |
Mr = 239.34 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 635 reflections |
a = 9.580 (3) Å | θ = 1.4–25.4° |
b = 9.552 (2) Å | µ = 0.25 mm−1 |
c = 13.677 (4) Å | T = 290 K |
β = 99.489 (4)° | Block, yellow |
V = 1234.3 (6) Å3 | 0.39 × 0.35 × 0.14 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2487 independent reflections |
Radiation source: fine-focus sealed tube | 2221 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
φ and ω scans | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.918, Tmax = 0.966 | k = −11→11 |
9377 measured reflections | l = −17→14 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.102 | All H-atom parameters refined |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.2147P] where P = (Fo2 + 2Fc2)/3 |
2487 reflections | (Δ/σ)max < 0.001 |
213 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.32 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 | 0.25611 (5) | 0.17947 (4) | −0.10628 (3) | 0.04896 (16) | |
O1 | 0.03961 (12) | 0.60020 (11) | −0.15671 (8) | 0.0528 (3) | |
O2 | 0.14741 (11) | 0.65327 (10) | −0.00392 (7) | 0.0425 (3) | |
N1 | 0.09238 (19) | 0.34733 (17) | −0.23394 (10) | 0.0590 (4) | |
C1 | 0.41463 (18) | 0.15512 (18) | 0.08495 (14) | 0.0496 (4) | |
C2 | 0.55979 (18) | 0.2232 (2) | 0.11716 (15) | 0.0598 (5) | |
C3 | 0.5614 (2) | 0.3450 (2) | 0.18778 (14) | 0.0599 (5) | |
C4 | 0.4744 (2) | 0.4727 (2) | 0.14909 (13) | 0.0552 (4) | |
C5 | 0.31499 (18) | 0.44758 (18) | 0.12288 (11) | 0.0456 (4) | |
C6 | 0.27150 (14) | 0.37440 (14) | 0.02496 (9) | 0.0339 (3) | |
C7 | 0.31707 (15) | 0.24280 (15) | 0.01218 (11) | 0.0394 (3) | |
C8 | 0.18273 (14) | 0.42880 (13) | −0.06361 (9) | 0.0339 (3) | |
C9 | 0.16503 (16) | 0.33208 (14) | −0.14055 (11) | 0.0401 (3) | |
C10 | 0.11639 (14) | 0.56516 (14) | −0.08002 (10) | 0.0354 (3) | |
C11 | 0.08966 (17) | 0.79327 (15) | −0.01557 (12) | 0.0439 (4) | |
C12 | 0.1438 (2) | 0.8687 (2) | 0.07877 (16) | 0.0601 (5) | |
H1 | 0.041 (2) | 0.422 (2) | −0.2416 (15) | 0.067 (6)* | |
H2 | 0.069 (2) | 0.275 (2) | −0.2670 (16) | 0.063 (6)* | |
H3 | 0.2837 (19) | 0.388 (2) | 0.1748 (14) | 0.058 (5)* | |
H4 | 0.265 (2) | 0.531 (2) | 0.1256 (13) | 0.058 (5)* | |
H5 | 0.489 (2) | 0.543 (2) | 0.1986 (17) | 0.074 (6)* | |
H6 | 0.509 (2) | 0.511 (2) | 0.0920 (15) | 0.061 (5)* | |
H7 | 0.658 (2) | 0.373 (2) | 0.2047 (16) | 0.076 (6)* | |
H8 | 0.527 (2) | 0.311 (2) | 0.2449 (16) | 0.064 (6)* | |
H9 | 0.623 (2) | 0.150 (2) | 0.1508 (15) | 0.066 (6)* | |
H10 | 0.593 (2) | 0.252 (2) | 0.0579 (17) | 0.068 (6)* | |
H11 | 0.371 (2) | 0.137 (2) | 0.1442 (15) | 0.064 (5)* | |
H12 | 0.4254 (19) | 0.061 (2) | 0.0568 (14) | 0.061 (5)* | |
H13 | 0.243 (3) | 0.874 (3) | 0.0876 (17) | 0.082 (7)* | |
H14 | 0.107 (3) | 0.823 (2) | 0.1343 (19) | 0.086 (7)* | |
H15 | 0.113 (2) | 0.960 (3) | 0.0750 (16) | 0.077 (6)* | |
H16 | −0.012 (2) | 0.7870 (18) | −0.0266 (12) | 0.047 (4)* | |
H17 | 0.1229 (18) | 0.8386 (17) | −0.0709 (14) | 0.046 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0678 (3) | 0.0341 (2) | 0.0430 (2) | 0.00392 (16) | 0.00321 (19) | −0.00549 (14) |
O1 | 0.0660 (7) | 0.0413 (6) | 0.0425 (6) | 0.0071 (5) | −0.0166 (5) | 0.0034 (5) |
O2 | 0.0497 (6) | 0.0336 (5) | 0.0395 (5) | 0.0073 (4) | −0.0062 (4) | −0.0022 (4) |
N1 | 0.0892 (12) | 0.0414 (8) | 0.0370 (7) | −0.0039 (8) | −0.0176 (7) | −0.0049 (6) |
C1 | 0.0511 (9) | 0.0436 (8) | 0.0524 (10) | 0.0106 (7) | 0.0039 (7) | 0.0104 (7) |
C2 | 0.0422 (9) | 0.0757 (12) | 0.0601 (11) | 0.0141 (8) | 0.0043 (8) | 0.0145 (10) |
C3 | 0.0426 (9) | 0.0847 (13) | 0.0476 (10) | −0.0043 (8) | −0.0071 (7) | 0.0119 (9) |
C4 | 0.0648 (11) | 0.0570 (10) | 0.0378 (9) | −0.0133 (8) | −0.0093 (8) | −0.0009 (7) |
C5 | 0.0551 (9) | 0.0471 (9) | 0.0309 (7) | 0.0096 (7) | −0.0034 (6) | −0.0020 (6) |
C6 | 0.0348 (6) | 0.0353 (7) | 0.0300 (7) | 0.0009 (5) | 0.0010 (5) | 0.0020 (5) |
C7 | 0.0424 (7) | 0.0375 (7) | 0.0369 (7) | 0.0019 (6) | 0.0029 (6) | 0.0030 (6) |
C8 | 0.0376 (7) | 0.0317 (6) | 0.0300 (6) | −0.0025 (5) | −0.0011 (5) | 0.0007 (5) |
C9 | 0.0504 (8) | 0.0332 (7) | 0.0336 (7) | −0.0058 (6) | −0.0017 (6) | 0.0011 (5) |
C10 | 0.0347 (7) | 0.0353 (7) | 0.0339 (7) | −0.0035 (5) | −0.0013 (5) | 0.0021 (5) |
C11 | 0.0451 (8) | 0.0325 (7) | 0.0516 (9) | 0.0045 (6) | 0.0006 (7) | 0.0000 (6) |
C12 | 0.0702 (13) | 0.0422 (9) | 0.0633 (12) | 0.0036 (9) | −0.0030 (9) | −0.0123 (8) |
Geometric parameters (Å, º) top
S1—C9 | 1.7236 (15) | C5—C4 | 1.529 (2) |
S1—C7 | 1.7377 (15) | C5—H3 | 1.00 (2) |
O2—C10 | 1.3334 (16) | C5—H4 | 0.929 (19) |
O2—C11 | 1.4459 (17) | C1—C2 | 1.532 (3) |
O1—C10 | 1.2242 (17) | C1—H11 | 0.99 (2) |
C6—C7 | 1.351 (2) | C1—H12 | 0.99 (2) |
C6—C8 | 1.4563 (18) | C4—C3 | 1.523 (3) |
C6—C5 | 1.5072 (19) | C4—H5 | 0.94 (2) |
C10—C8 | 1.4505 (19) | C4—H6 | 0.97 (2) |
C8—C9 | 1.3895 (19) | C12—H14 | 0.99 (2) |
C7—C1 | 1.503 (2) | C12—H15 | 0.92 (2) |
N1—C9 | 1.358 (2) | C12—H13 | 0.94 (3) |
N1—H1 | 0.87 (2) | C3—C2 | 1.511 (3) |
N1—H2 | 0.83 (2) | C3—H8 | 0.95 (2) |
C11—C12 | 1.494 (2) | C3—H7 | 0.95 (2) |
C11—H16 | 0.964 (18) | C2—H10 | 0.96 (2) |
C11—H17 | 0.970 (18) | C2—H9 | 0.99 (2) |
| | | |
C9—S1—C7 | 92.09 (7) | H3—C5—H4 | 104.2 (15) |
C10—O2—C11 | 117.75 (11) | C7—C1—C2 | 112.94 (14) |
C7—C6—C8 | 112.40 (12) | C7—C1—H11 | 109.9 (11) |
C7—C6—C5 | 119.90 (12) | C2—C1—H11 | 108.9 (12) |
C8—C6—C5 | 127.70 (12) | C7—C1—H12 | 110.0 (11) |
O1—C10—O2 | 121.42 (13) | C2—C1—H12 | 110.5 (11) |
O1—C10—C8 | 124.34 (13) | H11—C1—H12 | 104.2 (16) |
O2—C10—C8 | 114.23 (11) | C3—C4—C5 | 115.09 (15) |
C9—C8—C10 | 118.96 (12) | C3—C4—H5 | 108.0 (13) |
C9—C8—C6 | 111.99 (12) | C5—C4—H5 | 107.6 (13) |
C10—C8—C6 | 129.05 (12) | C3—C4—H6 | 109.8 (12) |
C6—C7—C1 | 127.70 (14) | C5—C4—H6 | 109.6 (12) |
C6—C7—S1 | 112.23 (10) | H5—C4—H6 | 106.4 (17) |
C1—C7—S1 | 120.01 (12) | C11—C12—H14 | 109.6 (14) |
C9—N1—H1 | 113.4 (14) | C11—C12—H15 | 110.3 (14) |
C9—N1—H2 | 118.2 (14) | H14—C12—H15 | 107.9 (19) |
H1—N1—H2 | 121.2 (19) | C11—C12—H13 | 109.6 (14) |
N1—C9—C8 | 128.37 (14) | H14—C12—H13 | 114 (2) |
N1—C9—S1 | 120.30 (12) | H15—C12—H13 | 106 (2) |
C8—C9—S1 | 111.30 (10) | C2—C3—C4 | 116.60 (15) |
O2—C11—C12 | 106.19 (13) | C2—C3—H8 | 107.1 (12) |
O2—C11—H16 | 108.6 (10) | C4—C3—H8 | 108.4 (12) |
C12—C11—H16 | 111.3 (10) | C2—C3—H7 | 106.1 (13) |
O2—C11—H17 | 109.3 (10) | C4—C3—H7 | 108.4 (13) |
C12—C11—H17 | 110.3 (10) | H8—C3—H7 | 110.2 (18) |
H16—C11—H17 | 111.0 (15) | C3—C2—C1 | 115.06 (16) |
C6—C5—C4 | 113.60 (14) | C3—C2—H10 | 110.3 (13) |
C6—C5—H3 | 107.2 (11) | C1—C2—H10 | 106.8 (12) |
C4—C5—H3 | 109.3 (10) | C3—C2—H9 | 107.8 (12) |
C6—C5—H4 | 111.2 (11) | C1—C2—H9 | 107.0 (12) |
C4—C5—H4 | 110.9 (12) | H10—C2—H9 | 109.6 (17) |
| | | |
C11—O2—C10—O1 | −1.3 (2) | C10—C8—C9—N1 | 0.8 (2) |
C11—O2—C10—C8 | 177.79 (12) | C6—C8—C9—N1 | −178.39 (16) |
O1—C10—C8—C9 | 3.2 (2) | C10—C8—C9—S1 | 178.43 (10) |
O2—C10—C8—C9 | −175.81 (12) | C6—C8—C9—S1 | −0.72 (15) |
O1—C10—C8—C6 | −177.77 (14) | C7—S1—C9—N1 | 178.61 (14) |
O2—C10—C8—C6 | 3.2 (2) | C7—S1—C9—C8 | 0.73 (12) |
C7—C6—C8—C9 | 0.32 (17) | C10—O2—C11—C12 | −178.65 (15) |
C5—C6—C8—C9 | 179.85 (14) | C7—C6—C5—C4 | 63.50 (19) |
C7—C6—C8—C10 | −178.73 (13) | C8—C6—C5—C4 | −116.00 (16) |
C5—C6—C8—C10 | 0.8 (2) | C6—C7—C1—C2 | −59.2 (2) |
C8—C6—C7—C1 | 177.33 (14) | S1—C7—C1—C2 | 117.67 (15) |
C5—C6—C7—C1 | −2.2 (2) | C6—C5—C4—C3 | −77.66 (19) |
C8—C6—C7—S1 | 0.23 (15) | C5—C4—C3—C2 | 63.2 (2) |
C5—C6—C7—S1 | −179.34 (11) | C4—C3—C2—C1 | −62.9 (2) |
C9—S1—C7—C6 | −0.55 (12) | C7—C1—C2—C3 | 73.9 (2) |
C9—S1—C7—C1 | −177.90 (13) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.87 (2) | 2.06 (2) | 2.717 (2) | 132 (2) |
N1—H2···O1i | 0.84 (2) | 2.15 (2) | 2.964 (2) | 166 (2) |
C5—H4···O2 | 0.93 (2) | 2.27 (2) | 2.920 (2) | 127 (1) |
C11—H16···Cg1ii | 0.96 (2) | 2.76 | 3.578 | 143 |
Symmetry codes: (i) −x, y−1/2, −z−1/2; (ii) −x, −y+1, −z. |