The title compound, C
15H
15ClN
2OS, shows antibacterial and antifungal activities. The dihedral angle between the thiophene moiety and the 2-chlorophenyl ring is 22.3 (1)°. There are intramolecular N—H
O and N—H
Cl hydrogen bonds and an intramolecular C—H
O interaction, which remove the conformational flexibility. Also intermolecular N—H
O interactions form chains of molecules in the crystal structure.
Supporting information
CCDC reference: 248852
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.052
- wR factor = 0.143
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.97 Ratio
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C14
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C11
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT352_ALERT_3_C Short N-H Bond (0.87A) N2 - H3N ... 0.76 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 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
3 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
0 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: SHELXS97 (Sheldrick, 1997); 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).
2-amino-
N-(2-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
top
Crystal data top
C15H15ClN2OS | F(000) = 640 |
Mr = 306.81 | Dx = 1.415 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 750 reflections |
a = 11.432 (3) Å | θ = 1.8–25.4° |
b = 14.722 (3) Å | µ = 0.41 mm−1 |
c = 9.321 (2) Å | T = 293 K |
β = 113.320 (3)° | Block, yellow |
V = 1440.5 (6) Å3 | 0.50 × 0.30 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2450 independent reflections |
Radiation source: fine-focus sealed tube | 2074 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −13→13 |
Tmin = 0.823, Tmax = 0.923 | k = −17→17 |
9632 measured reflections | l = −10→10 |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0706P)2 + 1.144P] where P = (Fo2 + 2Fc2)/3 |
2450 reflections | (Δ/σ)max < 0.001 |
241 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.67 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 | 0.61476 (8) | −0.11499 (5) | 0.28182 (9) | 0.0591 (3) | |
Cl1 | 0.89665 (13) | 0.19258 (6) | 0.91685 (12) | 0.1088 (5) | |
O1 | 0.7442 (2) | −0.14096 (14) | 0.8039 (2) | 0.0616 (6) | |
N1 | 0.6953 (3) | −0.22631 (18) | 0.5270 (4) | 0.0678 (8) | |
N2 | 0.7865 (3) | 0.00968 (18) | 0.8228 (3) | 0.0563 (6) | |
C1 | 0.6736 (3) | −0.13856 (18) | 0.4798 (3) | 0.0483 (6) | |
C2 | 0.6908 (2) | −0.06023 (17) | 0.5683 (3) | 0.0426 (6) | |
C3 | 0.6566 (2) | 0.02024 (17) | 0.4696 (3) | 0.0411 (6) | |
C4 | 0.6156 (3) | 0.00104 (18) | 0.3159 (3) | 0.0480 (6) | |
C5 | 0.6629 (3) | 0.11778 (17) | 0.5220 (3) | 0.0469 (6) | |
C6 | 0.5932 (3) | 0.1821 (2) | 0.3865 (3) | 0.0532 (7) | |
C7 | 0.6205 (4) | 0.1617 (2) | 0.2438 (4) | 0.0581 (8) | |
C8 | 0.5741 (4) | 0.0671 (2) | 0.1823 (3) | 0.0584 (8) | |
C9 | 0.7409 (3) | −0.06784 (18) | 0.7385 (3) | 0.0467 (6) | |
C10 | 0.8458 (3) | 0.0217 (2) | 0.9851 (3) | 0.0537 (7) | |
C11 | 0.9005 (3) | 0.1056 (2) | 1.0439 (4) | 0.0589 (8) | |
C12 | 0.9607 (3) | 0.1217 (3) | 1.2022 (4) | 0.0743 (10) | |
C13 | 0.9669 (5) | 0.0546 (4) | 1.3046 (5) | 0.1034 (17) | |
C14 | 0.9132 (5) | −0.0268 (5) | 1.2502 (5) | 0.122 (2) | |
C15 | 0.8530 (4) | −0.0444 (4) | 1.0922 (4) | 0.0904 (14) | |
H1N | 0.721 (3) | −0.234 (2) | 0.625 (4) | 0.064 (10)* | |
H2N | 0.702 (4) | −0.265 (3) | 0.464 (5) | 0.088 (13)* | |
H3N | 0.792 (4) | 0.051 (3) | 0.777 (4) | 0.073 (12)* | |
H5A | 0.626 (3) | 0.123 (2) | 0.597 (4) | 0.059 (9)* | |
H5B | 0.753 (3) | 0.137 (2) | 0.573 (3) | 0.054 (8)* | |
H6A | 0.619 (3) | 0.245 (2) | 0.421 (4) | 0.068 (9)* | |
H6B | 0.501 (3) | 0.176 (2) | 0.360 (3) | 0.055 (8)* | |
H7A | 0.581 (3) | 0.204 (2) | 0.161 (4) | 0.069 (9)* | |
H7B | 0.710 (3) | 0.162 (2) | 0.275 (4) | 0.055 (9)* | |
H8A | 0.479 (4) | 0.066 (2) | 0.129 (4) | 0.076 (11)* | |
H8B | 0.608 (3) | 0.049 (2) | 0.109 (4) | 0.058 (8)* | |
H12 | 1.000 (3) | 0.179 (3) | 1.232 (4) | 0.075 (11)* | |
H13 | 1.010 (4) | 0.067 (3) | 1.403 (6) | 0.113 (15)* | |
H14 | 0.918 (5) | −0.071 (4) | 1.326 (7) | 0.141 (19)* | |
H15 | 0.825 (5) | −0.101 (3) | 1.054 (6) | 0.122 (17)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0910 (6) | 0.0421 (4) | 0.0502 (4) | −0.0122 (3) | 0.0343 (4) | −0.0129 (3) |
Cl1 | 0.1572 (11) | 0.0434 (5) | 0.0731 (6) | 0.0053 (5) | −0.0106 (6) | −0.0010 (4) |
O1 | 0.0772 (14) | 0.0508 (12) | 0.0515 (11) | −0.0058 (10) | 0.0199 (10) | 0.0093 (9) |
N1 | 0.110 (2) | 0.0375 (14) | 0.0659 (19) | 0.0026 (14) | 0.0456 (18) | −0.0012 (13) |
N2 | 0.0744 (17) | 0.0472 (14) | 0.0399 (13) | 0.0018 (12) | 0.0147 (12) | −0.0005 (11) |
C1 | 0.0591 (16) | 0.0386 (13) | 0.0536 (16) | −0.0043 (12) | 0.0290 (13) | −0.0039 (12) |
C2 | 0.0482 (14) | 0.0373 (13) | 0.0440 (14) | −0.0012 (11) | 0.0201 (11) | −0.0026 (10) |
C3 | 0.0446 (14) | 0.0382 (13) | 0.0418 (13) | −0.0016 (11) | 0.0184 (11) | −0.0035 (10) |
C4 | 0.0617 (17) | 0.0406 (14) | 0.0434 (14) | −0.0074 (12) | 0.0227 (13) | −0.0069 (11) |
C5 | 0.0586 (18) | 0.0391 (14) | 0.0405 (14) | 0.0017 (12) | 0.0171 (13) | −0.0039 (11) |
C6 | 0.067 (2) | 0.0419 (16) | 0.0489 (16) | 0.0056 (14) | 0.0206 (14) | 0.0022 (12) |
C7 | 0.077 (2) | 0.0485 (17) | 0.0487 (16) | −0.0036 (15) | 0.0243 (16) | 0.0054 (13) |
C8 | 0.080 (2) | 0.0536 (17) | 0.0399 (15) | −0.0051 (15) | 0.0224 (15) | −0.0017 (13) |
C9 | 0.0483 (15) | 0.0451 (15) | 0.0466 (14) | 0.0030 (12) | 0.0185 (12) | 0.0020 (12) |
C10 | 0.0489 (15) | 0.0675 (19) | 0.0425 (14) | 0.0031 (14) | 0.0158 (12) | −0.0039 (13) |
C11 | 0.0553 (17) | 0.0601 (18) | 0.0521 (16) | 0.0146 (14) | 0.0116 (13) | −0.0077 (14) |
C12 | 0.060 (2) | 0.098 (3) | 0.058 (2) | 0.0000 (19) | 0.0162 (16) | −0.025 (2) |
C13 | 0.097 (3) | 0.165 (5) | 0.0418 (19) | −0.046 (3) | 0.020 (2) | −0.017 (3) |
C14 | 0.140 (4) | 0.169 (5) | 0.045 (2) | −0.079 (4) | 0.023 (2) | 0.007 (3) |
C15 | 0.103 (3) | 0.116 (3) | 0.0440 (18) | −0.049 (3) | 0.0201 (18) | 0.003 (2) |
Geometric parameters (Å, º) top
S1—C1 | 1.731 (3) | C6—C7 | 1.512 (4) |
S1—C4 | 1.737 (3) | C6—H6B | 0.99 (3) |
Cl1—C11 | 1.733 (3) | C6—H6A | 0.99 (3) |
O1—C9 | 1.230 (3) | C7—C8 | 1.519 (4) |
N2—C9 | 1.366 (4) | C7—H7B | 0.94 (3) |
N2—C10 | 1.403 (4) | C7—H7A | 0.96 (4) |
N2—H3N | 0.76 (4) | C11—C12 | 1.380 (5) |
N1—C1 | 1.356 (4) | C11—C10 | 1.394 (4) |
N1—H1N | 0.85 (4) | C8—H8B | 0.95 (3) |
N1—H2N | 0.84 (4) | C8—H8A | 1.00 (4) |
C2—C1 | 1.386 (4) | C10—C15 | 1.373 (5) |
C2—C3 | 1.455 (4) | C12—C13 | 1.356 (6) |
C2—C9 | 1.462 (4) | C12—H12 | 0.95 (4) |
C3—C4 | 1.349 (4) | C15—C14 | 1.381 (5) |
C3—C5 | 1.509 (3) | C15—H15 | 0.91 (5) |
C4—C8 | 1.502 (4) | C13—C14 | 1.349 (7) |
C5—C6 | 1.527 (4) | C13—H13 | 0.87 (5) |
C5—H5A | 0.95 (3) | C14—H14 | 0.94 (6) |
C5—H5B | 0.99 (3) | | |
| | | |
C1—S1—C4 | 91.75 (12) | C5—C6—H6A | 109 (2) |
C9—N2—C10 | 129.6 (3) | H6B—C6—H6A | 108 (3) |
C9—N2—H3N | 116 (3) | C6—C7—C8 | 110.6 (3) |
C10—N2—H3N | 113 (3) | C6—C7—H7B | 107.7 (19) |
C1—N1—H1N | 115 (2) | C8—C7—H7B | 107.3 (19) |
C1—N1—H2N | 118 (3) | C6—C7—H7A | 112 (2) |
H1N—N1—H2N | 124 (4) | C8—C7—H7A | 108 (2) |
C1—C2—C3 | 111.2 (2) | H7B—C7—H7A | 110 (3) |
C1—C2—C9 | 118.9 (2) | C12—C11—C10 | 121.9 (3) |
C3—C2—C9 | 129.8 (2) | C12—C11—Cl1 | 118.1 (3) |
C4—C3—C2 | 113.2 (2) | C10—C11—Cl1 | 120.0 (2) |
C4—C3—C5 | 119.7 (2) | C4—C8—C7 | 109.4 (2) |
C2—C3—C5 | 127.1 (2) | C4—C8—H8B | 109.2 (19) |
C3—C4—C8 | 127.4 (2) | C7—C8—H8B | 110.7 (19) |
C3—C4—S1 | 112.0 (2) | C4—C8—H8A | 109 (2) |
C8—C4—S1 | 120.6 (2) | C7—C8—H8A | 111 (2) |
C3—C5—C6 | 112.4 (2) | H8B—C8—H8A | 108 (3) |
C3—C5—H5A | 109.5 (19) | C15—C10—C11 | 117.0 (3) |
C6—C5—H5A | 108.7 (19) | C15—C10—N2 | 124.0 (3) |
C3—C5—H5B | 109.2 (17) | C11—C10—N2 | 119.0 (3) |
C6—C5—H5B | 109.3 (17) | C13—C12—C11 | 119.5 (4) |
H5A—C5—H5B | 108 (3) | C13—C12—H12 | 124 (2) |
N1—C1—C2 | 129.5 (3) | C11—C12—H12 | 116 (2) |
N1—C1—S1 | 118.7 (2) | C10—C15—C14 | 120.2 (4) |
C2—C1—S1 | 111.8 (2) | C10—C15—H15 | 117 (3) |
O1—C9—N2 | 121.1 (3) | C14—C15—H15 | 122 (3) |
O1—C9—C2 | 121.8 (2) | C14—C13—C12 | 119.6 (4) |
N2—C9—C2 | 117.1 (2) | C14—C13—H13 | 125 (3) |
C7—C6—C5 | 112.5 (3) | C12—C13—H13 | 116 (3) |
C7—C6—H6B | 109.7 (17) | C13—C14—C15 | 121.8 (5) |
C5—C6—H6B | 107.6 (17) | C13—C14—H14 | 116 (4) |
C7—C6—H6A | 109.6 (19) | C15—C14—H14 | 122 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1 | 0.85 (3) | 2.09 (3) | 2.722 (4) | 131 (3) |
N2—H3N···Cl1 | 0.77 (4) | 2.50 (4) | 2.955 (3) | 120 (3) |
C15—H15···O1 | 0.91 (4) | 2.22 (5) | 2.854 (4) | 126 (4) |
N1—H2N···O1i | 0.84 (4) | 2.22 (5) | 3.062 (4) | 173 (4) |
Symmetry code: (i) x, −y−1/2, z−1/2. |