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In the structure of the title compound, C12H17NO2S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012808/ob6500sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012808/ob6500Isup2.hkl
Contains datablock I

CCDC reference: 274597

Key indicators

  • Single-crystal X-ray study
  • T = 290 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.038
  • wR factor = 0.102
  • Data-to-parameter ratio = 11.7

checkCIF/PLATON results

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Computing details top

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-4H-cyclohepta[b]thiophene-3-carboxylate top
Crystal data top
C12H17NO2SF(000) = 512
Mr = 239.34Dx = 1.288 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 635 reflections
a = 9.580 (3) Åθ = 1.4–25.4°
b = 9.552 (2) ŵ = 0.25 mm1
c = 13.677 (4) ÅT = 290 K
β = 99.489 (4)°Block, yellow
V = 1234.3 (6) Å30.39 × 0.35 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
2487 independent reflections
Radiation source: fine-focus sealed tube2221 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
φ and ω scansθmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.918, Tmax = 0.966k = 1111
9377 measured reflectionsl = 1714
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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102All 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 parametersΔρmax = 0.20 e Å3
0 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*/Ueq
S10.25611 (5)0.17947 (4)0.10628 (3)0.04896 (16)
O10.03961 (12)0.60020 (11)0.15671 (8)0.0528 (3)
O20.14741 (11)0.65327 (10)0.00392 (7)0.0425 (3)
N10.09238 (19)0.34733 (17)0.23394 (10)0.0590 (4)
C10.41463 (18)0.15512 (18)0.08495 (14)0.0496 (4)
C20.55979 (18)0.2232 (2)0.11716 (15)0.0598 (5)
C30.5614 (2)0.3450 (2)0.18778 (14)0.0599 (5)
C40.4744 (2)0.4727 (2)0.14909 (13)0.0552 (4)
C50.31499 (18)0.44758 (18)0.12288 (11)0.0456 (4)
C60.27150 (14)0.37440 (14)0.02496 (9)0.0339 (3)
C70.31707 (15)0.24280 (15)0.01218 (11)0.0394 (3)
C80.18273 (14)0.42880 (13)0.06361 (9)0.0339 (3)
C90.16503 (16)0.33208 (14)0.14055 (11)0.0401 (3)
C100.11639 (14)0.56516 (14)0.08002 (10)0.0354 (3)
C110.08966 (17)0.79327 (15)0.01557 (12)0.0439 (4)
C120.1438 (2)0.8687 (2)0.07877 (16)0.0601 (5)
H10.041 (2)0.422 (2)0.2416 (15)0.067 (6)*
H20.069 (2)0.275 (2)0.2670 (16)0.063 (6)*
H30.2837 (19)0.388 (2)0.1748 (14)0.058 (5)*
H40.265 (2)0.531 (2)0.1256 (13)0.058 (5)*
H50.489 (2)0.543 (2)0.1986 (17)0.074 (6)*
H60.509 (2)0.511 (2)0.0920 (15)0.061 (5)*
H70.658 (2)0.373 (2)0.2047 (16)0.076 (6)*
H80.527 (2)0.311 (2)0.2449 (16)0.064 (6)*
H90.623 (2)0.150 (2)0.1508 (15)0.066 (6)*
H100.593 (2)0.252 (2)0.0579 (17)0.068 (6)*
H110.371 (2)0.137 (2)0.1442 (15)0.064 (5)*
H120.4254 (19)0.061 (2)0.0568 (14)0.061 (5)*
H130.243 (3)0.874 (3)0.0876 (17)0.082 (7)*
H140.107 (3)0.823 (2)0.1343 (19)0.086 (7)*
H150.113 (2)0.960 (3)0.0750 (16)0.077 (6)*
H160.012 (2)0.7870 (18)0.0266 (12)0.047 (4)*
H170.1229 (18)0.8386 (17)0.0709 (14)0.046 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0678 (3)0.0341 (2)0.0430 (2)0.00392 (16)0.00321 (19)0.00549 (14)
O10.0660 (7)0.0413 (6)0.0425 (6)0.0071 (5)0.0166 (5)0.0034 (5)
O20.0497 (6)0.0336 (5)0.0395 (5)0.0073 (4)0.0062 (4)0.0022 (4)
N10.0892 (12)0.0414 (8)0.0370 (7)0.0039 (8)0.0176 (7)0.0049 (6)
C10.0511 (9)0.0436 (8)0.0524 (10)0.0106 (7)0.0039 (7)0.0104 (7)
C20.0422 (9)0.0757 (12)0.0601 (11)0.0141 (8)0.0043 (8)0.0145 (10)
C30.0426 (9)0.0847 (13)0.0476 (10)0.0043 (8)0.0071 (7)0.0119 (9)
C40.0648 (11)0.0570 (10)0.0378 (9)0.0133 (8)0.0093 (8)0.0009 (7)
C50.0551 (9)0.0471 (9)0.0309 (7)0.0096 (7)0.0034 (6)0.0020 (6)
C60.0348 (6)0.0353 (7)0.0300 (7)0.0009 (5)0.0010 (5)0.0020 (5)
C70.0424 (7)0.0375 (7)0.0369 (7)0.0019 (6)0.0029 (6)0.0030 (6)
C80.0376 (7)0.0317 (6)0.0300 (6)0.0025 (5)0.0011 (5)0.0007 (5)
C90.0504 (8)0.0332 (7)0.0336 (7)0.0058 (6)0.0017 (6)0.0011 (5)
C100.0347 (7)0.0353 (7)0.0339 (7)0.0035 (5)0.0013 (5)0.0021 (5)
C110.0451 (8)0.0325 (7)0.0516 (9)0.0045 (6)0.0006 (7)0.0000 (6)
C120.0702 (13)0.0422 (9)0.0633 (12)0.0036 (9)0.0030 (9)0.0123 (8)
Geometric parameters (Å, º) top
S1—C91.7236 (15)C5—C41.529 (2)
S1—C71.7377 (15)C5—H31.00 (2)
O2—C101.3334 (16)C5—H40.929 (19)
O2—C111.4459 (17)C1—C21.532 (3)
O1—C101.2242 (17)C1—H110.99 (2)
C6—C71.351 (2)C1—H120.99 (2)
C6—C81.4563 (18)C4—C31.523 (3)
C6—C51.5072 (19)C4—H50.94 (2)
C10—C81.4505 (19)C4—H60.97 (2)
C8—C91.3895 (19)C12—H140.99 (2)
C7—C11.503 (2)C12—H150.92 (2)
N1—C91.358 (2)C12—H130.94 (3)
N1—H10.87 (2)C3—C21.511 (3)
N1—H20.83 (2)C3—H80.95 (2)
C11—C121.494 (2)C3—H70.95 (2)
C11—H160.964 (18)C2—H100.96 (2)
C11—H170.970 (18)C2—H90.99 (2)
C9—S1—C792.09 (7)H3—C5—H4104.2 (15)
C10—O2—C11117.75 (11)C7—C1—C2112.94 (14)
C7—C6—C8112.40 (12)C7—C1—H11109.9 (11)
C7—C6—C5119.90 (12)C2—C1—H11108.9 (12)
C8—C6—C5127.70 (12)C7—C1—H12110.0 (11)
O1—C10—O2121.42 (13)C2—C1—H12110.5 (11)
O1—C10—C8124.34 (13)H11—C1—H12104.2 (16)
O2—C10—C8114.23 (11)C3—C4—C5115.09 (15)
C9—C8—C10118.96 (12)C3—C4—H5108.0 (13)
C9—C8—C6111.99 (12)C5—C4—H5107.6 (13)
C10—C8—C6129.05 (12)C3—C4—H6109.8 (12)
C6—C7—C1127.70 (14)C5—C4—H6109.6 (12)
C6—C7—S1112.23 (10)H5—C4—H6106.4 (17)
C1—C7—S1120.01 (12)C11—C12—H14109.6 (14)
C9—N1—H1113.4 (14)C11—C12—H15110.3 (14)
C9—N1—H2118.2 (14)H14—C12—H15107.9 (19)
H1—N1—H2121.2 (19)C11—C12—H13109.6 (14)
N1—C9—C8128.37 (14)H14—C12—H13114 (2)
N1—C9—S1120.30 (12)H15—C12—H13106 (2)
C8—C9—S1111.30 (10)C2—C3—C4116.60 (15)
O2—C11—C12106.19 (13)C2—C3—H8107.1 (12)
O2—C11—H16108.6 (10)C4—C3—H8108.4 (12)
C12—C11—H16111.3 (10)C2—C3—H7106.1 (13)
O2—C11—H17109.3 (10)C4—C3—H7108.4 (13)
C12—C11—H17110.3 (10)H8—C3—H7110.2 (18)
H16—C11—H17111.0 (15)C3—C2—C1115.06 (16)
C6—C5—C4113.60 (14)C3—C2—H10110.3 (13)
C6—C5—H3107.2 (11)C1—C2—H10106.8 (12)
C4—C5—H3109.3 (10)C3—C2—H9107.8 (12)
C6—C5—H4111.2 (11)C1—C2—H9107.0 (12)
C4—C5—H4110.9 (12)H10—C2—H9109.6 (17)
C11—O2—C10—O11.3 (2)C10—C8—C9—N10.8 (2)
C11—O2—C10—C8177.79 (12)C6—C8—C9—N1178.39 (16)
O1—C10—C8—C93.2 (2)C10—C8—C9—S1178.43 (10)
O2—C10—C8—C9175.81 (12)C6—C8—C9—S10.72 (15)
O1—C10—C8—C6177.77 (14)C7—S1—C9—N1178.61 (14)
O2—C10—C8—C63.2 (2)C7—S1—C9—C80.73 (12)
C7—C6—C8—C90.32 (17)C10—O2—C11—C12178.65 (15)
C5—C6—C8—C9179.85 (14)C7—C6—C5—C463.50 (19)
C7—C6—C8—C10178.73 (13)C8—C6—C5—C4116.00 (16)
C5—C6—C8—C100.8 (2)C6—C7—C1—C259.2 (2)
C8—C6—C7—C1177.33 (14)S1—C7—C1—C2117.67 (15)
C5—C6—C7—C12.2 (2)C6—C5—C4—C377.66 (19)
C8—C6—C7—S10.23 (15)C5—C4—C3—C263.2 (2)
C5—C6—C7—S1179.34 (11)C4—C3—C2—C162.9 (2)
C9—S1—C7—C60.55 (12)C7—C1—C2—C373.9 (2)
C9—S1—C7—C1177.90 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.87 (2)2.06 (2)2.717 (2)132 (2)
N1—H2···O1i0.84 (2)2.15 (2)2.964 (2)166 (2)
C5—H4···O20.93 (2)2.27 (2)2.920 (2)127 (1)
C11—H16···Cg1ii0.96 (2)2.763.578143
Symmetry codes: (i) x, y1/2, z1/2; (ii) x, y+1, z.
 

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