In the title compound, C
13H
14N
2O
2S, the dihedral angle between the furan and cyclopentathiophene groups is 89.88 (14)°. The carboximidamide unit is in an anticlinal conformation with respect to the cycloheptathiophene moiety and an intramolecular N—H
O hydrogen bond closes an
S(6) ring. In the crystal, N—H
O hydogen bonds link the molecules into [010]
C(6) chains and a very weak C—H
O interaction is also observed.
Supporting information
CCDC reference: 1570199
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.120
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT420_ALERT_2_C D-H Without Acceptor N2 -- H1N ... Please Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ...... 4.688 Check
Alert level G
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms .............. 2 Report
PLAT128_ALERT_4_G Alternate Setting for Input Space Group C2/c I2/a Note
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 273 Check
PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 273 Check
PLAT398_ALERT_2_G Deviating C-O-C Angle from 120 Deg for O1 105.9 Degree
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 3 Note
PLAT961_ALERT_5_G Dataset Contains no Negative Intensities ....... Please Check
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density. 5 Info
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
8 ALERT level G = General information/check it is not something unexpected
2 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
1 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
2 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
2-Amino-
N-(furan-2-ylmethyl)-5,6-dihydro-4
H-cyclopenta[
b]thiophene-3-carboxamide
top
Crystal data top
C13H14N2O2S | F(000) = 1104 |
Mr = 262.32 | Dx = 1.443 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 2375 reflections |
a = 21.694 (2) Å | θ = 2.4–26.0° |
b = 9.8547 (11) Å | µ = 0.26 mm−1 |
c = 15.1162 (16) Å | T = 273 K |
β = 131.661 (2)° | Block, pale yellow |
V = 2414.3 (4) Å3 | 0.28 × 0.25 × 0.22 mm |
Z = 8 | |
Data collection top
Bruker APEXII CCD diffractometer | Rint = 0.026 |
Detector resolution: 18.4 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω and φ scans | h = −25→26 |
9118 measured reflections | k = −11→12 |
2375 independent reflections | l = −18→18 |
1950 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.120 | W = 1/[Σ2(FO2) + (0.0768P)2 + 1.5332P] WHERE P = (FO2 + 2FC2)/3 |
S = 0.94 | (Δ/σ)max < 0.001 |
2375 reflections | Δρmax = 0.25 e Å−3 |
167 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the
rounded fractional coordinates. All su's are estimated
from the variances of the (full) variance-covariance matrix.
The cell esds are taken into account in the estimation of
distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those
flagged by the user for potential systematic errors.
Weighted R-factors wR and all goodnesses of fit S
are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The
observed criterion of F2 > 2sigma(F2) is used only
for calculating -R-factor-obs 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 | 0.20078 (3) | 0.46023 (5) | 0.33918 (5) | 0.0417 (2) | |
O1 | −0.01010 (9) | 1.03238 (16) | 0.12373 (13) | 0.0494 (5) | |
O2 | 0.20894 (9) | 0.91283 (14) | 0.28657 (13) | 0.0419 (5) | |
N1 | 0.24893 (11) | 0.65497 (18) | 0.27274 (16) | 0.0460 (6) | |
N2 | 0.13634 (11) | 0.94561 (16) | 0.34213 (16) | 0.0369 (6) | |
C1 | 0.09466 (13) | 0.6855 (2) | 0.42005 (18) | 0.0387 (6) | |
C2 | 0.13894 (11) | 0.64691 (19) | 0.37874 (15) | 0.0315 (5) | |
C3 | 0.07541 (17) | 0.5480 (2) | 0.4461 (3) | 0.0579 (9) | |
C4 | 0.11271 (15) | 0.4340 (2) | 0.4249 (2) | 0.0481 (8) | |
C5 | 0.14820 (12) | 0.5112 (2) | 0.38300 (17) | 0.0374 (6) | |
C6 | 0.20996 (11) | 0.62804 (19) | 0.31246 (16) | 0.0323 (6) | |
C7 | 0.17454 (11) | 0.71866 (18) | 0.33821 (15) | 0.0296 (5) | |
C8 | 0.17492 (11) | 0.86383 (19) | 0.32061 (15) | 0.0307 (5) | |
C9 | 0.12394 (12) | 1.08935 (19) | 0.31397 (17) | 0.0357 (6) | |
C10 | 0.05629 (11) | 1.11794 (19) | 0.18473 (17) | 0.0341 (6) | |
C11 | 0.04371 (14) | 1.2137 (2) | 0.11172 (19) | 0.0488 (7) | |
C12 | −0.03482 (14) | 1.1888 (2) | −0.00186 (19) | 0.0520 (8) | |
C13 | −0.06404 (14) | 1.0795 (3) | 0.0094 (2) | 0.0530 (8) | |
H1A | 0.25426 | 0.73747 | 0.26020 | 0.0550* | |
H1B | 0.26842 | 0.58963 | 0.25995 | 0.0550* | |
H1D | 0.04431 | 0.73478 | 0.35898 | 0.0460* | |
H1E | 0.12945 | 0.74105 | 0.49084 | 0.0460* | |
H1N | 0.1123 (15) | 0.914 (2) | 0.359 (2) | 0.047 (7)* | |
H3A | 0.09891 | 0.54570 | 0.52755 | 0.0700* | |
H3B | 0.01619 | 0.53591 | 0.39458 | 0.0700* | |
H4A | 0.15513 | 0.38489 | 0.49735 | 0.0580* | |
H4B | 0.07068 | 0.37072 | 0.36516 | 0.0580* | |
H9A | 0.17493 | 1.12798 | 0.34037 | 0.0430* | |
H9B | 0.11115 | 1.13391 | 0.35731 | 0.0430* | |
H11 | 0.07968 | 1.28374 | 0.13150 | 0.0590* | |
H12 | −0.06040 | 1.23942 | −0.07033 | 0.0620* | |
H13 | −0.11455 | 1.03962 | −0.05200 | 0.0640* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0525 (3) | 0.0264 (3) | 0.0565 (4) | −0.0005 (2) | 0.0405 (3) | −0.0038 (2) |
O1 | 0.0473 (9) | 0.0544 (10) | 0.0507 (9) | −0.0160 (7) | 0.0344 (8) | −0.0103 (7) |
O2 | 0.0565 (9) | 0.0323 (7) | 0.0596 (9) | −0.0007 (6) | 0.0481 (8) | 0.0022 (6) |
N1 | 0.0646 (12) | 0.0324 (9) | 0.0711 (12) | 0.0011 (8) | 0.0578 (11) | −0.0032 (8) |
N2 | 0.0517 (10) | 0.0271 (9) | 0.0492 (10) | 0.0024 (7) | 0.0408 (9) | 0.0029 (7) |
C1 | 0.0446 (11) | 0.0370 (11) | 0.0448 (11) | −0.0010 (9) | 0.0340 (10) | −0.0001 (9) |
C2 | 0.0326 (9) | 0.0309 (10) | 0.0309 (9) | −0.0025 (7) | 0.0211 (8) | −0.0023 (7) |
C3 | 0.0780 (17) | 0.0436 (14) | 0.0860 (18) | −0.0057 (11) | 0.0687 (16) | 0.0008 (12) |
C4 | 0.0580 (13) | 0.0365 (12) | 0.0608 (14) | −0.0056 (10) | 0.0441 (12) | 0.0013 (10) |
C5 | 0.0424 (11) | 0.0311 (10) | 0.0430 (11) | −0.0037 (8) | 0.0302 (10) | −0.0023 (8) |
C6 | 0.0346 (10) | 0.0287 (10) | 0.0345 (9) | −0.0025 (7) | 0.0234 (8) | −0.0038 (7) |
C7 | 0.0314 (9) | 0.0283 (10) | 0.0306 (9) | −0.0017 (7) | 0.0213 (8) | −0.0022 (7) |
C8 | 0.0324 (9) | 0.0300 (10) | 0.0297 (9) | −0.0003 (7) | 0.0207 (8) | −0.0014 (7) |
C9 | 0.0449 (11) | 0.0256 (10) | 0.0430 (11) | 0.0003 (8) | 0.0319 (10) | −0.0029 (8) |
C10 | 0.0374 (10) | 0.0280 (9) | 0.0438 (11) | −0.0017 (8) | 0.0299 (9) | −0.0061 (8) |
C11 | 0.0503 (13) | 0.0365 (12) | 0.0469 (12) | −0.0049 (10) | 0.0270 (11) | 0.0013 (9) |
C12 | 0.0537 (14) | 0.0502 (14) | 0.0418 (12) | 0.0107 (11) | 0.0274 (11) | 0.0032 (10) |
C13 | 0.0396 (12) | 0.0718 (17) | 0.0449 (13) | −0.0038 (11) | 0.0269 (11) | −0.0131 (11) |
Geometric parameters (Å, º) top
S1—C5 | 1.731 (3) | C6—C7 | 1.392 (3) |
S1—C6 | 1.745 (2) | C7—C8 | 1.456 (3) |
O1—C10 | 1.368 (3) | C9—C10 | 1.496 (3) |
O1—C13 | 1.372 (3) | C10—C11 | 1.335 (3) |
O2—C8 | 1.244 (3) | C11—C12 | 1.422 (3) |
N1—C6 | 1.349 (4) | C12—C13 | 1.317 (4) |
N2—C8 | 1.348 (4) | C1—H1D | 0.9700 |
N2—C9 | 1.452 (2) | C1—H1E | 0.9700 |
C1—C2 | 1.502 (4) | C3—H3A | 0.9700 |
C1—C3 | 1.544 (4) | C3—H3B | 0.9700 |
N1—H1A | 0.8600 | C4—H4A | 0.9700 |
N1—H1B | 0.8600 | C4—H4B | 0.9700 |
N2—H1N | 0.78 (4) | C9—H9A | 0.9700 |
C2—C5 | 1.348 (3) | C9—H9B | 0.9700 |
C2—C7 | 1.449 (4) | C11—H11 | 0.9300 |
C3—C4 | 1.538 (5) | C12—H12 | 0.9300 |
C4—C5 | 1.490 (4) | C13—H13 | 0.9300 |
| | | |
C5—S1—C6 | 91.10 (12) | C10—C11—C12 | 107.4 (2) |
C10—O1—C13 | 106.0 (2) | C11—C12—C13 | 106.2 (2) |
C8—N2—C9 | 122.4 (2) | O1—C13—C12 | 111.0 (2) |
C2—C1—C3 | 103.9 (2) | C2—C1—H1D | 111.00 |
C6—N1—H1B | 120.00 | C2—C1—H1E | 111.00 |
H1A—N1—H1B | 120.00 | C3—C1—H1D | 111.00 |
C6—N1—H1A | 120.00 | C3—C1—H1E | 111.00 |
C1—C2—C5 | 110.4 (2) | H1D—C1—H1E | 109.00 |
C1—C2—C7 | 136.07 (18) | C1—C3—H3A | 110.00 |
C8—N2—H1N | 119.8 (18) | C1—C3—H3B | 110.00 |
C9—N2—H1N | 116.8 (19) | C4—C3—H3A | 110.00 |
C5—C2—C7 | 113.6 (2) | C4—C3—H3B | 110.00 |
C1—C3—C4 | 108.6 (3) | H3A—C3—H3B | 108.00 |
C3—C4—C5 | 102.0 (2) | C3—C4—H4A | 111.00 |
C2—C5—C4 | 115.1 (2) | C3—C4—H4B | 111.00 |
S1—C5—C2 | 112.6 (2) | C5—C4—H4A | 111.00 |
S1—C5—C4 | 132.26 (17) | C5—C4—H4B | 111.00 |
S1—C6—N1 | 119.41 (17) | H4A—C4—H4B | 109.00 |
S1—C6—C7 | 111.98 (19) | N2—C9—H9A | 109.00 |
N1—C6—C7 | 128.61 (19) | N2—C9—H9B | 109.00 |
C2—C7—C6 | 110.71 (17) | C10—C9—H9A | 109.00 |
C6—C7—C8 | 120.5 (2) | C10—C9—H9B | 109.00 |
C2—C7—C8 | 128.7 (2) | H9A—C9—H9B | 108.00 |
O2—C8—C7 | 122.3 (2) | C10—C11—H11 | 126.00 |
N2—C8—C7 | 117.6 (2) | C12—C11—H11 | 126.00 |
O2—C8—N2 | 120.13 (18) | C11—C12—H12 | 127.00 |
N2—C9—C10 | 113.35 (16) | C13—C12—H12 | 127.00 |
O1—C10—C9 | 116.34 (18) | O1—C13—H13 | 125.00 |
O1—C10—C11 | 109.48 (19) | C12—C13—H13 | 124.00 |
C9—C10—C11 | 134.2 (2) | | |
| | | |
C6—S1—C5—C2 | −0.58 (17) | C1—C2—C7—C6 | 179.0 (2) |
C6—S1—C5—C4 | −179.9 (2) | C1—C2—C7—C8 | −2.5 (4) |
C5—S1—C6—N1 | −179.91 (18) | C1—C3—C4—C5 | −2.3 (3) |
C5—S1—C6—C7 | 0.76 (16) | C3—C4—C5—S1 | −179.6 (2) |
C13—O1—C10—C9 | 178.8 (2) | C3—C4—C5—C2 | 1.1 (3) |
C13—O1—C10—C11 | 0.3 (3) | S1—C6—C7—C2 | −0.7 (2) |
C10—O1—C13—C12 | −0.8 (3) | N1—C6—C7—C8 | 1.4 (3) |
C9—N2—C8—O2 | 7.5 (3) | S1—C6—C7—C8 | −179.33 (14) |
C9—N2—C8—C7 | −172.27 (18) | N1—C6—C7—C2 | −180.0 (2) |
C8—N2—C9—C10 | 76.0 (3) | C2—C7—C8—O2 | 179.03 (19) |
C2—C1—C3—C4 | 2.7 (3) | C2—C7—C8—N2 | −1.2 (3) |
C3—C1—C2—C5 | −2.1 (3) | C6—C7—C8—O2 | −2.7 (3) |
C3—C1—C2—C7 | 179.2 (2) | C6—C7—C8—N2 | 177.07 (18) |
C1—C2—C5—S1 | −178.78 (14) | N2—C9—C10—O1 | 35.1 (4) |
C1—C2—C5—C4 | 0.7 (3) | N2—C9—C10—C11 | −147.0 (3) |
C7—C2—C5—S1 | 0.3 (2) | O1—C10—C11—C12 | 0.2 (3) |
C7—C2—C5—C4 | 179.70 (18) | C9—C10—C11—C12 | −177.8 (3) |
C5—C2—C7—C8 | 178.76 (19) | C10—C11—C12—C13 | −0.7 (4) |
C5—C2—C7—C6 | 0.3 (2) | C11—C12—C13—O1 | 0.9 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.86 | 2.15 | 2.738 (3) | 125 |
N1—H1B···O2i | 0.86 | 2.06 | 2.902 (3) | 167 |
C9—H9B···O1ii | 0.97 | 2.59 | 3.224 (4) | 123 |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x, y, −z+1/2. |