Download citation
Download citation
link to html
In the title compound, C13H14N2O2S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2414314617012111/hb4165sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2414314617012111/hb4165Isup2.hkl
Contains datablock I

CCDC reference: 1570199

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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

Computing details top

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-4H-cyclopenta[b]thiophene-3-carboxamide top
Crystal data top
C13H14N2O2SF(000) = 1104
Mr = 262.32Dx = 1.443 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2375 reflections
a = 21.694 (2) Åθ = 2.4–26.0°
b = 9.8547 (11) ŵ = 0.26 mm1
c = 15.1162 (16) ÅT = 273 K
β = 131.661 (2)°Block, pale yellow
V = 2414.3 (4) Å30.28 × 0.25 × 0.22 mm
Z = 8
Data collection top
Bruker APEXII CCD
diffractometer
Rint = 0.026
Detector resolution: 18.4 pixels mm-1θmax = 26.0°, θmin = 2.4°
ω and φ scansh = 2526
9118 measured reflectionsk = 1112
2375 independent reflectionsl = 1818
1950 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.043H 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 reflectionsΔρmax = 0.25 e Å3
167 parametersΔρmin = 0.27 e Å3
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
xyzUiso*/Ueq
S10.20078 (3)0.46023 (5)0.33918 (5)0.0417 (2)
O10.01010 (9)1.03238 (16)0.12373 (13)0.0494 (5)
O20.20894 (9)0.91283 (14)0.28657 (13)0.0419 (5)
N10.24893 (11)0.65497 (18)0.27274 (16)0.0460 (6)
N20.13634 (11)0.94561 (16)0.34213 (16)0.0369 (6)
C10.09466 (13)0.6855 (2)0.42005 (18)0.0387 (6)
C20.13894 (11)0.64691 (19)0.37874 (15)0.0315 (5)
C30.07541 (17)0.5480 (2)0.4461 (3)0.0579 (9)
C40.11271 (15)0.4340 (2)0.4249 (2)0.0481 (8)
C50.14820 (12)0.5112 (2)0.38300 (17)0.0374 (6)
C60.20996 (11)0.62804 (19)0.31246 (16)0.0323 (6)
C70.17454 (11)0.71866 (18)0.33821 (15)0.0296 (5)
C80.17492 (11)0.86383 (19)0.32061 (15)0.0307 (5)
C90.12394 (12)1.08935 (19)0.31397 (17)0.0357 (6)
C100.05629 (11)1.11794 (19)0.18473 (17)0.0341 (6)
C110.04371 (14)1.2137 (2)0.11172 (19)0.0488 (7)
C120.03482 (14)1.1888 (2)0.00186 (19)0.0520 (8)
C130.06404 (14)1.0795 (3)0.0094 (2)0.0530 (8)
H1A0.254260.737470.260200.0550*
H1B0.268420.589630.259950.0550*
H1D0.044310.734780.358980.0460*
H1E0.129450.741050.490840.0460*
H1N0.1123 (15)0.914 (2)0.359 (2)0.047 (7)*
H3A0.098910.545700.527550.0700*
H3B0.016190.535910.394580.0700*
H4A0.155130.384890.497350.0580*
H4B0.070680.370720.365160.0580*
H9A0.174931.127980.340370.0430*
H9B0.111151.133910.357310.0430*
H110.079681.283740.131500.0590*
H120.060401.239420.070330.0620*
H130.114551.039620.052000.0640*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0525 (3)0.0264 (3)0.0565 (4)0.0005 (2)0.0405 (3)0.0038 (2)
O10.0473 (9)0.0544 (10)0.0507 (9)0.0160 (7)0.0344 (8)0.0103 (7)
O20.0565 (9)0.0323 (7)0.0596 (9)0.0007 (6)0.0481 (8)0.0022 (6)
N10.0646 (12)0.0324 (9)0.0711 (12)0.0011 (8)0.0578 (11)0.0032 (8)
N20.0517 (10)0.0271 (9)0.0492 (10)0.0024 (7)0.0408 (9)0.0029 (7)
C10.0446 (11)0.0370 (11)0.0448 (11)0.0010 (9)0.0340 (10)0.0001 (9)
C20.0326 (9)0.0309 (10)0.0309 (9)0.0025 (7)0.0211 (8)0.0023 (7)
C30.0780 (17)0.0436 (14)0.0860 (18)0.0057 (11)0.0687 (16)0.0008 (12)
C40.0580 (13)0.0365 (12)0.0608 (14)0.0056 (10)0.0441 (12)0.0013 (10)
C50.0424 (11)0.0311 (10)0.0430 (11)0.0037 (8)0.0302 (10)0.0023 (8)
C60.0346 (10)0.0287 (10)0.0345 (9)0.0025 (7)0.0234 (8)0.0038 (7)
C70.0314 (9)0.0283 (10)0.0306 (9)0.0017 (7)0.0213 (8)0.0022 (7)
C80.0324 (9)0.0300 (10)0.0297 (9)0.0003 (7)0.0207 (8)0.0014 (7)
C90.0449 (11)0.0256 (10)0.0430 (11)0.0003 (8)0.0319 (10)0.0029 (8)
C100.0374 (10)0.0280 (9)0.0438 (11)0.0017 (8)0.0299 (9)0.0061 (8)
C110.0503 (13)0.0365 (12)0.0469 (12)0.0049 (10)0.0270 (11)0.0013 (9)
C120.0537 (14)0.0502 (14)0.0418 (12)0.0107 (11)0.0274 (11)0.0032 (10)
C130.0396 (12)0.0718 (17)0.0449 (13)0.0038 (11)0.0269 (11)0.0131 (11)
Geometric parameters (Å, º) top
S1—C51.731 (3)C6—C71.392 (3)
S1—C61.745 (2)C7—C81.456 (3)
O1—C101.368 (3)C9—C101.496 (3)
O1—C131.372 (3)C10—C111.335 (3)
O2—C81.244 (3)C11—C121.422 (3)
N1—C61.349 (4)C12—C131.317 (4)
N2—C81.348 (4)C1—H1D0.9700
N2—C91.452 (2)C1—H1E0.9700
C1—C21.502 (4)C3—H3A0.9700
C1—C31.544 (4)C3—H3B0.9700
N1—H1A0.8600C4—H4A0.9700
N1—H1B0.8600C4—H4B0.9700
N2—H1N0.78 (4)C9—H9A0.9700
C2—C51.348 (3)C9—H9B0.9700
C2—C71.449 (4)C11—H110.9300
C3—C41.538 (5)C12—H120.9300
C4—C51.490 (4)C13—H130.9300
C5—S1—C691.10 (12)C10—C11—C12107.4 (2)
C10—O1—C13106.0 (2)C11—C12—C13106.2 (2)
C8—N2—C9122.4 (2)O1—C13—C12111.0 (2)
C2—C1—C3103.9 (2)C2—C1—H1D111.00
C6—N1—H1B120.00C2—C1—H1E111.00
H1A—N1—H1B120.00C3—C1—H1D111.00
C6—N1—H1A120.00C3—C1—H1E111.00
C1—C2—C5110.4 (2)H1D—C1—H1E109.00
C1—C2—C7136.07 (18)C1—C3—H3A110.00
C8—N2—H1N119.8 (18)C1—C3—H3B110.00
C9—N2—H1N116.8 (19)C4—C3—H3A110.00
C5—C2—C7113.6 (2)C4—C3—H3B110.00
C1—C3—C4108.6 (3)H3A—C3—H3B108.00
C3—C4—C5102.0 (2)C3—C4—H4A111.00
C2—C5—C4115.1 (2)C3—C4—H4B111.00
S1—C5—C2112.6 (2)C5—C4—H4A111.00
S1—C5—C4132.26 (17)C5—C4—H4B111.00
S1—C6—N1119.41 (17)H4A—C4—H4B109.00
S1—C6—C7111.98 (19)N2—C9—H9A109.00
N1—C6—C7128.61 (19)N2—C9—H9B109.00
C2—C7—C6110.71 (17)C10—C9—H9A109.00
C6—C7—C8120.5 (2)C10—C9—H9B109.00
C2—C7—C8128.7 (2)H9A—C9—H9B108.00
O2—C8—C7122.3 (2)C10—C11—H11126.00
N2—C8—C7117.6 (2)C12—C11—H11126.00
O2—C8—N2120.13 (18)C11—C12—H12127.00
N2—C9—C10113.35 (16)C13—C12—H12127.00
O1—C10—C9116.34 (18)O1—C13—H13125.00
O1—C10—C11109.48 (19)C12—C13—H13124.00
C9—C10—C11134.2 (2)
C6—S1—C5—C20.58 (17)C1—C2—C7—C6179.0 (2)
C6—S1—C5—C4179.9 (2)C1—C2—C7—C82.5 (4)
C5—S1—C6—N1179.91 (18)C1—C3—C4—C52.3 (3)
C5—S1—C6—C70.76 (16)C3—C4—C5—S1179.6 (2)
C13—O1—C10—C9178.8 (2)C3—C4—C5—C21.1 (3)
C13—O1—C10—C110.3 (3)S1—C6—C7—C20.7 (2)
C10—O1—C13—C120.8 (3)N1—C6—C7—C81.4 (3)
C9—N2—C8—O27.5 (3)S1—C6—C7—C8179.33 (14)
C9—N2—C8—C7172.27 (18)N1—C6—C7—C2180.0 (2)
C8—N2—C9—C1076.0 (3)C2—C7—C8—O2179.03 (19)
C2—C1—C3—C42.7 (3)C2—C7—C8—N21.2 (3)
C3—C1—C2—C52.1 (3)C6—C7—C8—O22.7 (3)
C3—C1—C2—C7179.2 (2)C6—C7—C8—N2177.07 (18)
C1—C2—C5—S1178.78 (14)N2—C9—C10—O135.1 (4)
C1—C2—C5—C40.7 (3)N2—C9—C10—C11147.0 (3)
C7—C2—C5—S10.3 (2)O1—C10—C11—C120.2 (3)
C7—C2—C5—C4179.70 (18)C9—C10—C11—C12177.8 (3)
C5—C2—C7—C8178.76 (19)C10—C11—C12—C130.7 (4)
C5—C2—C7—C60.3 (2)C11—C12—C13—O10.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O20.862.152.738 (3)125
N1—H1B···O2i0.862.062.902 (3)167
C9—H9B···O1ii0.972.593.224 (4)123
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x, y, z+1/2.
 

Follow IUCrData
Sign up for e-alerts
Follow IUCrData on Twitter
Follow us on facebook
Sign up for RSS feeds