The title compound, C
16H
18N
2O
2S, shows antibacterial and antifungal activities. The dihedral angle between the thiophene and 2-methylphenyl groups is 83.3 (1)°. There are intra- and intermolecular N—H
O hydrogen bonds, and C—H
O intermolecular interactions.
Supporting information
CCDC reference: 251728
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.123
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A
ABSTM02_ALERT_3_A Test not performed as the _exptl_absorpt_correction_type
has not been identified. See test ABSTY_01.
ABSTY01_ALERT_1_A The absorption correction should be one of the following
* none
* analytical
* integration
* numerical
* gaussian
* empirical
* psi-scan
* multi-scan
* refdelf
* sphere
* cylinder
2 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
0 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 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
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: 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).
2-(acetamido)-4,5-dimethyl-
N-(2-methylphenyl)thiophene-3-carboxamide
top
Crystal data top
C16H18N2O2S | F(000) = 640 |
Mr = 302.39 | Dx = 1.293 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 650 reflections |
a = 7.416 (2) Å | θ = 2.5–24.5° |
b = 8.858 (3) Å | µ = 0.21 mm−1 |
c = 23.718 (8) Å | T = 293 K |
β = 94.566 (6)° | Block, yellow |
V = 1553.2 (9) Å3 | 0.50 × 0.20 × 0.20 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3118 independent reflections |
Radiation source: fine-focus sealed tube | 2715 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.910, Tmax = 0.958 | k = −11→11 |
11711 measured reflections | l = −29→28 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.1357P)2 + 0.8P] where P = (Fo2 + 2Fc2)/3 |
3118 reflections | (Δ/σ)max = 0.001 |
202 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.16 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 | 0.25473 (6) | 0.59444 (5) | −0.056475 (17) | 0.03998 (17) | |
O1 | 0.2861 (2) | 0.18448 (14) | 0.05964 (5) | 0.0511 (4) | |
O2 | 0.3785 (2) | 0.38323 (16) | −0.13044 (5) | 0.0520 (4) | |
N1 | 0.3368 (2) | 0.35218 (17) | 0.13111 (6) | 0.0437 (4) | |
N2 | 0.3211 (2) | 0.29163 (17) | −0.04514 (6) | 0.0404 (3) | |
C1 | 0.2810 (2) | 0.42759 (17) | −0.01966 (7) | 0.0339 (3) | |
C2 | 0.2575 (2) | 0.44524 (18) | 0.03693 (7) | 0.0339 (3) | |
C3 | 0.2086 (2) | 0.59902 (18) | 0.05010 (7) | 0.0368 (4) | |
C4 | 0.2040 (2) | 0.68968 (19) | 0.00397 (8) | 0.0409 (4) | |
C5 | 0.2921 (2) | 0.31688 (18) | 0.07608 (7) | 0.0374 (4) | |
C6 | 0.3909 (3) | 0.2442 (2) | 0.17378 (7) | 0.0452 (4) | |
C7 | 0.2723 (3) | 0.1328 (2) | 0.18960 (8) | 0.0534 (5) | |
C8 | 0.3383 (4) | 0.0347 (3) | 0.23321 (10) | 0.0732 (7) | |
C9 | 0.5087 (5) | 0.0495 (3) | 0.25967 (10) | 0.0827 (9) | |
C10 | 0.6207 (4) | 0.1616 (4) | 0.24427 (9) | 0.0787 (8) | |
C11 | 0.5626 (3) | 0.2590 (3) | 0.20091 (9) | 0.0627 (6) | |
C12 | 0.0840 (4) | 0.1182 (3) | 0.16399 (11) | 0.0756 (7) | |
C13 | 0.1539 (3) | 0.6536 (2) | 0.10626 (8) | 0.0494 (4) | |
C14 | 0.1594 (3) | 0.8547 (2) | −0.00080 (10) | 0.0619 (6) | |
C15 | 0.3679 (2) | 0.2755 (2) | −0.09890 (7) | 0.0426 (4) | |
C16 | 0.4032 (4) | 0.1154 (3) | −0.11619 (10) | 0.0661 (6) | |
H1N | 0.373 (3) | 0.435 (2) | 0.1359 (8) | 0.045 (6)* | |
H2N | 0.315 (3) | 0.218 (2) | −0.0238 (8) | 0.043 (5)* | |
H8 | 0.2641 | −0.0425 | 0.2444 | 0.088* | |
H9 | 0.5480 | −0.0173 | 0.2883 | 0.099* | |
H10 | 0.7354 | 0.1725 | 0.2627 | 0.094* | |
H11 | 0.6392 | 0.3348 | 0.1899 | 0.075* | |
H12A | 0.0333 | 0.2169 | 0.1572 | 0.113* | |
H12B | 0.0128 | 0.0640 | 0.1894 | 0.113* | |
H12C | 0.0840 | 0.0644 | 0.1289 | 0.113* | |
H13A | 0.2598 | 0.6664 | 0.1318 | 0.074* | |
H13B | 0.0751 | 0.5809 | 0.1215 | 0.074* | |
H13C | 0.0919 | 0.7484 | 0.1013 | 0.074* | |
H14A | 0.0382 | 0.8711 | 0.0094 | 0.093* | |
H14B | 0.1690 | 0.8875 | −0.0390 | 0.093* | |
H14C | 0.2424 | 0.9111 | 0.0242 | 0.093* | |
H16A | 0.2903 | 0.0656 | −0.1262 | 0.099* | |
H16B | 0.4668 | 0.0630 | −0.0853 | 0.099* | |
H16C | 0.4751 | 0.1156 | −0.1481 | 0.099* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0439 (3) | 0.0389 (3) | 0.0367 (3) | 0.00068 (16) | 0.00020 (18) | 0.00730 (16) |
O1 | 0.0834 (10) | 0.0324 (7) | 0.0375 (7) | −0.0030 (6) | 0.0044 (6) | 0.0004 (5) |
O2 | 0.0666 (9) | 0.0555 (8) | 0.0340 (6) | −0.0042 (6) | 0.0047 (6) | 0.0014 (6) |
N1 | 0.0641 (10) | 0.0335 (8) | 0.0329 (7) | −0.0023 (7) | −0.0007 (6) | 0.0004 (6) |
N2 | 0.0514 (9) | 0.0354 (8) | 0.0347 (7) | 0.0009 (6) | 0.0049 (6) | −0.0002 (6) |
C1 | 0.0340 (8) | 0.0334 (8) | 0.0337 (8) | −0.0012 (6) | −0.0005 (6) | 0.0015 (6) |
C2 | 0.0354 (8) | 0.0328 (8) | 0.0332 (8) | −0.0023 (6) | 0.0014 (6) | −0.0011 (6) |
C3 | 0.0344 (8) | 0.0346 (8) | 0.0410 (9) | −0.0003 (6) | −0.0002 (7) | −0.0020 (6) |
C4 | 0.0401 (9) | 0.0356 (9) | 0.0465 (9) | 0.0022 (7) | −0.0007 (7) | 0.0009 (7) |
C5 | 0.0433 (9) | 0.0360 (8) | 0.0332 (8) | −0.0031 (7) | 0.0042 (7) | 0.0007 (6) |
C6 | 0.0628 (11) | 0.0437 (9) | 0.0297 (8) | 0.0087 (8) | 0.0077 (7) | 0.0009 (7) |
C7 | 0.0694 (13) | 0.0515 (11) | 0.0415 (9) | 0.0088 (9) | 0.0188 (9) | 0.0049 (8) |
C8 | 0.108 (2) | 0.0639 (14) | 0.0525 (12) | 0.0181 (13) | 0.0351 (13) | 0.0195 (11) |
C9 | 0.114 (2) | 0.097 (2) | 0.0391 (11) | 0.0480 (18) | 0.0186 (13) | 0.0226 (12) |
C10 | 0.0865 (18) | 0.108 (2) | 0.0399 (11) | 0.0297 (16) | −0.0059 (11) | 0.0021 (13) |
C11 | 0.0700 (14) | 0.0768 (15) | 0.0400 (10) | 0.0062 (11) | −0.0042 (9) | −0.0004 (10) |
C12 | 0.0761 (17) | 0.0783 (16) | 0.0746 (16) | −0.0134 (13) | 0.0209 (13) | 0.0113 (13) |
C13 | 0.0536 (11) | 0.0465 (10) | 0.0486 (10) | 0.0062 (8) | 0.0066 (8) | −0.0092 (8) |
C14 | 0.0770 (15) | 0.0389 (10) | 0.0687 (14) | 0.0129 (10) | −0.0018 (11) | 0.0037 (9) |
C15 | 0.0448 (9) | 0.0481 (10) | 0.0347 (8) | −0.0030 (7) | 0.0010 (7) | −0.0049 (7) |
C16 | 0.0947 (17) | 0.0539 (12) | 0.0519 (12) | 0.0000 (11) | 0.0192 (11) | −0.0132 (10) |
Geometric parameters (Å, º) top
S1—C1 | 1.7199 (16) | C13—H13B | 0.9600 |
S1—C4 | 1.7306 (19) | C13—H13C | 0.9600 |
O1—C5 | 1.236 (2) | C7—C8 | 1.409 (3) |
O2—C15 | 1.219 (2) | C7—C12 | 1.484 (4) |
N2—C15 | 1.355 (2) | C14—H14A | 0.9600 |
N2—C1 | 1.390 (2) | C14—H14B | 0.9600 |
N2—H2N | 0.83 (2) | C14—H14C | 0.9600 |
N1—C5 | 1.357 (2) | C16—H16A | 0.9600 |
N1—C6 | 1.427 (2) | C16—H16B | 0.9600 |
N1—H1N | 0.79 (2) | C16—H16C | 0.9600 |
C2—C1 | 1.376 (2) | C11—C10 | 1.385 (3) |
C2—C3 | 1.450 (2) | C11—H11 | 0.9300 |
C2—C5 | 1.478 (2) | C8—C9 | 1.372 (4) |
C3—C4 | 1.355 (3) | C8—H8 | 0.9300 |
C3—C13 | 1.503 (2) | C12—H12A | 0.9600 |
C4—C14 | 1.501 (3) | C12—H12B | 0.9600 |
C15—C16 | 1.505 (3) | C12—H12C | 0.9600 |
C6—C11 | 1.387 (3) | C10—C9 | 1.363 (5) |
C6—C7 | 1.393 (3) | C10—H10 | 0.9300 |
C13—H13A | 0.9600 | C9—H9 | 0.9300 |
| | | |
C1—S1—C4 | 91.25 (8) | C6—C7—C8 | 116.4 (2) |
C15—N2—C1 | 125.44 (16) | C6—C7—C12 | 123.03 (19) |
C15—N2—H2N | 121.5 (14) | C8—C7—C12 | 120.5 (2) |
C1—N2—H2N | 113.1 (14) | C4—C14—H14A | 109.5 |
C5—N1—C6 | 124.12 (15) | C4—C14—H14B | 109.5 |
C5—N1—H1N | 114.1 (15) | H14A—C14—H14B | 109.5 |
C6—N1—H1N | 116.8 (15) | C4—C14—H14C | 109.5 |
C1—C2—C3 | 111.72 (14) | H14A—C14—H14C | 109.5 |
C1—C2—C5 | 119.77 (14) | H14B—C14—H14C | 109.5 |
C3—C2—C5 | 128.42 (15) | C15—C16—H16A | 109.5 |
C4—C3—C2 | 111.93 (15) | C15—C16—H16B | 109.5 |
C4—C3—C13 | 122.24 (16) | H16A—C16—H16B | 109.5 |
C2—C3—C13 | 125.66 (15) | C15—C16—H16C | 109.5 |
C2—C1—N2 | 124.79 (15) | H16A—C16—H16C | 109.5 |
C2—C1—S1 | 112.30 (12) | H16B—C16—H16C | 109.5 |
N2—C1—S1 | 122.91 (13) | C10—C11—C6 | 120.4 (3) |
C3—C4—C14 | 129.00 (18) | C10—C11—H11 | 119.8 |
C3—C4—S1 | 112.74 (13) | C6—C11—H11 | 119.8 |
C14—C4—S1 | 118.25 (15) | C9—C8—C7 | 122.1 (2) |
O1—C5—N1 | 121.47 (15) | C9—C8—H8 | 119.0 |
O1—C5—C2 | 122.14 (15) | C7—C8—H8 | 119.0 |
N1—C5—C2 | 116.35 (14) | C7—C12—H12A | 109.5 |
O2—C15—N2 | 121.92 (17) | C7—C12—H12B | 109.5 |
O2—C15—C16 | 123.32 (16) | H12A—C12—H12B | 109.5 |
N2—C15—C16 | 114.76 (17) | C7—C12—H12C | 109.5 |
C11—C6—C7 | 121.21 (19) | H12A—C12—H12C | 109.5 |
C11—C6—N1 | 117.49 (19) | H12B—C12—H12C | 109.5 |
C7—C6—N1 | 121.22 (18) | C9—C10—C11 | 119.5 (3) |
C3—C13—H13A | 109.5 | C9—C10—H10 | 120.2 |
C3—C13—H13B | 109.5 | C11—C10—H10 | 120.2 |
H13A—C13—H13B | 109.5 | C10—C9—C8 | 120.4 (2) |
C3—C13—H13C | 109.5 | C10—C9—H9 | 119.8 |
H13A—C13—H13C | 109.5 | C8—C9—H9 | 119.8 |
H13B—C13—H13C | 109.5 | | |
| | | |
C1—C2—C3—C4 | −2.1 (2) | C1—C2—C5—O1 | −23.2 (2) |
C5—C2—C3—C4 | 174.31 (15) | C3—C2—C5—O1 | 160.59 (17) |
C1—C2—C3—C13 | 173.14 (16) | C1—C2—C5—N1 | 154.78 (15) |
C5—C2—C3—C13 | −10.4 (3) | C3—C2—C5—N1 | −21.4 (2) |
C3—C2—C1—N2 | −177.25 (15) | C1—N2—C15—O2 | −0.2 (3) |
C5—C2—C1—N2 | 6.0 (2) | C1—N2—C15—C16 | −179.62 (17) |
C3—C2—C1—S1 | 2.59 (17) | C5—N1—C6—C11 | 118.8 (2) |
C5—C2—C1—S1 | −174.21 (12) | C5—N1—C6—C7 | −64.4 (2) |
C15—N2—C1—C2 | −170.81 (16) | C11—C6—C7—C8 | −1.7 (3) |
C15—N2—C1—S1 | 9.4 (2) | N1—C6—C7—C8 | −178.39 (17) |
C4—S1—C1—C2 | −1.86 (13) | C11—C6—C7—C12 | 176.4 (2) |
C4—S1—C1—N2 | 177.98 (14) | N1—C6—C7—C12 | −0.2 (3) |
C2—C3—C4—C14 | 179.87 (18) | C7—C6—C11—C10 | 0.7 (3) |
C13—C3—C4—C14 | 4.4 (3) | N1—C6—C11—C10 | 177.46 (18) |
C2—C3—C4—S1 | 0.73 (19) | C6—C7—C8—C9 | 1.5 (3) |
C13—C3—C4—S1 | −174.73 (13) | C12—C7—C8—C9 | −176.8 (2) |
C1—S1—C4—C3 | 0.62 (14) | C6—C11—C10—C9 | 0.8 (3) |
C1—S1—C4—C14 | −178.63 (16) | C11—C10—C9—C8 | −1.1 (4) |
C6—N1—C5—O1 | 4.0 (3) | C7—C8—C9—C10 | −0.1 (4) |
C6—N1—C5—C2 | −174.04 (16) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.786 (19) | 2.46 (2) | 3.155 (2) | 148 (2) |
N2—H2N···O1 | 0.829 (18) | 2.029 (19) | 2.692 (2) | 137 (2) |
C14—H14C···O1ii | 0.96 | 2.58 | 3.355 (3) | 138 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x, y+1, z. |