In the title compound, C
18H
14BrN
3O
2S, the three rings are nearly coplanar. In the crystal structure, intermolecular N—H
N and C—H
O hydrogen-bond interactions link the molecules into ribbons, displaying alternate rings of graph-set motifs
R22(8) and
R22(14).
Supporting information
CCDC reference: 272101
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.009 Å
- R factor = 0.068
- wR factor = 0.185
- Data-to-parameter ratio = 17.2
checkCIF/PLATON results
No syntax errors found
Alert level C
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.119
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16
PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 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
3 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXTL.
N-[5-(1E)-Styryl-1,3,4-thiadiazol-2-yl]-4-Bromophenoxy-acetamide
top
Crystal data top
C18H14BrN3O2S | Z = 2 |
Mr = 416.29 | F(000) = 420 |
Triclinic, P1 | Dx = 1.544 Mg m−3 |
Hall symbol: -p 1 | Melting point: 525 K |
a = 5.1151 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.5790 (18) Å | Cell parameters from 1434 reflections |
c = 18.426 (3) Å | θ = 2.4–19.8° |
α = 87.292 (3)° | µ = 2.43 mm−1 |
β = 83.782 (3)° | T = 292 K |
γ = 87.021 (4)° | Plate, colourless |
V = 895.5 (3) Å3 | 0.40 × 0.16 × 0.04 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 3898 independent reflections |
Radiation source: fine-focus sealed tube | 1930 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.119 |
φ and ω scans | θmax = 27.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −6→6 |
Tmin = 0.443, Tmax = 0.909 | k = −12→12 |
10201 measured reflections | l = −23→23 |
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)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0683P)2] where P = (Fo2 + 2Fc2)/3 |
3898 reflections | (Δ/σ)max < 0.001 |
226 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.38 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 | |
Br1 | 0.97554 (17) | 0.28458 (9) | 0.17115 (4) | 0.1080 (4) | |
C1 | 0.2912 (14) | 1.2773 (8) | 0.9059 (3) | 0.086 (2) | |
H1 | 0.1581 | 1.3171 | 0.8799 | 0.103* | |
C2 | 0.3349 (18) | 1.3324 (9) | 0.9718 (4) | 0.108 (3) | |
H2 | 0.2307 | 1.4081 | 0.9899 | 0.130* | |
C3 | 0.531 (2) | 1.2750 (11) | 1.0095 (4) | 0.108 (3) | |
H3 | 0.5585 | 1.3113 | 1.0539 | 0.130* | |
C4 | 0.6852 (18) | 1.1660 (10) | 0.9835 (4) | 0.111 (3) | |
H4 | 0.8212 | 1.1289 | 1.0093 | 0.134* | |
C5 | 0.6411 (15) | 1.1099 (8) | 0.9189 (3) | 0.092 (2) | |
H5 | 0.7463 | 1.0338 | 0.9017 | 0.110* | |
C6 | 0.4417 (12) | 1.1650 (6) | 0.8787 (3) | 0.0625 (16) | |
C7 | 0.4037 (12) | 1.1019 (6) | 0.8106 (3) | 0.0652 (16) | |
H7 | 0.5219 | 1.0290 | 0.7959 | 0.078* | |
C8 | 0.2180 (11) | 1.1374 (6) | 0.7673 (3) | 0.0602 (15) | |
H8 | 0.0943 | 1.2074 | 0.7826 | 0.072* | |
C9 | 0.1918 (11) | 1.0765 (6) | 0.6983 (3) | 0.0551 (14) | |
C10 | 0.2230 (9) | 0.9565 (5) | 0.5878 (3) | 0.0451 (12) | |
C11 | 0.4672 (10) | 0.7761 (5) | 0.5185 (3) | 0.0464 (12) | |
C12 | 0.4607 (10) | 0.6983 (5) | 0.4504 (3) | 0.0517 (13) | |
H12A | 0.3012 | 0.6469 | 0.4534 | 0.062* | |
H12B | 0.4625 | 0.7634 | 0.4084 | 0.062* | |
C13 | 0.7298 (10) | 0.5363 (5) | 0.3789 (3) | 0.0466 (12) | |
C14 | 0.9436 (10) | 0.4403 (5) | 0.3761 (3) | 0.0525 (13) | |
H14 | 1.0389 | 0.4267 | 0.4163 | 0.063* | |
C15 | 1.0149 (11) | 0.3664 (6) | 0.3156 (3) | 0.0638 (16) | |
H15 | 1.1577 | 0.3021 | 0.3143 | 0.077* | |
C16 | 0.8737 (11) | 0.3874 (6) | 0.2560 (3) | 0.0590 (15) | |
C17 | 0.6547 (11) | 0.4795 (6) | 0.2580 (3) | 0.0610 (15) | |
H17 | 0.5562 | 0.4907 | 0.2184 | 0.073* | |
C18 | 0.5862 (10) | 0.5540 (6) | 0.3198 (3) | 0.0576 (14) | |
H18 | 0.4412 | 0.6170 | 0.3217 | 0.069* | |
N1 | 0.0149 (9) | 1.1232 (5) | 0.6556 (2) | 0.0596 (12) | |
N2 | 0.0361 (8) | 1.0545 (5) | 0.5914 (2) | 0.0548 (11) | |
N3 | 0.2708 (8) | 0.8757 (4) | 0.5278 (2) | 0.0493 (11) | |
H3A | 0.1687 | 0.8893 | 0.4937 | 0.059* | |
O1 | 0.6273 (7) | 0.7544 (4) | 0.5618 (2) | 0.0668 (11) | |
O2 | 0.6827 (7) | 0.6051 (4) | 0.44261 (19) | 0.0594 (10) | |
S1 | 0.3988 (3) | 0.94143 (15) | 0.66190 (7) | 0.0556 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.1300 (8) | 0.1207 (7) | 0.0743 (5) | 0.0266 (5) | −0.0123 (5) | −0.0462 (5) |
C1 | 0.097 (5) | 0.096 (5) | 0.068 (4) | −0.005 (4) | −0.017 (4) | −0.021 (4) |
C2 | 0.127 (7) | 0.116 (7) | 0.084 (5) | −0.012 (6) | 0.000 (5) | −0.049 (5) |
C3 | 0.124 (7) | 0.145 (8) | 0.065 (5) | −0.047 (6) | −0.023 (5) | −0.022 (5) |
C4 | 0.116 (7) | 0.153 (9) | 0.073 (5) | −0.016 (6) | −0.037 (5) | −0.014 (5) |
C5 | 0.095 (5) | 0.117 (6) | 0.067 (4) | −0.003 (5) | −0.024 (4) | −0.012 (4) |
C6 | 0.067 (4) | 0.075 (4) | 0.046 (3) | −0.017 (3) | −0.002 (3) | −0.007 (3) |
C7 | 0.065 (4) | 0.071 (4) | 0.060 (4) | −0.001 (3) | −0.007 (3) | −0.008 (3) |
C8 | 0.062 (4) | 0.062 (4) | 0.057 (3) | −0.004 (3) | 0.000 (3) | −0.014 (3) |
C9 | 0.057 (3) | 0.061 (4) | 0.049 (3) | −0.003 (3) | −0.007 (3) | −0.007 (3) |
C10 | 0.039 (3) | 0.054 (3) | 0.043 (3) | 0.001 (3) | −0.010 (2) | −0.008 (2) |
C11 | 0.044 (3) | 0.047 (3) | 0.049 (3) | 0.004 (2) | −0.012 (2) | −0.001 (2) |
C12 | 0.048 (3) | 0.055 (3) | 0.052 (3) | 0.014 (3) | −0.012 (2) | −0.008 (3) |
C13 | 0.044 (3) | 0.046 (3) | 0.051 (3) | 0.003 (2) | −0.009 (2) | −0.006 (2) |
C14 | 0.048 (3) | 0.054 (3) | 0.056 (3) | 0.009 (3) | −0.014 (3) | −0.009 (3) |
C15 | 0.057 (4) | 0.062 (4) | 0.072 (4) | 0.010 (3) | −0.007 (3) | −0.015 (3) |
C16 | 0.063 (4) | 0.062 (4) | 0.051 (3) | −0.003 (3) | −0.002 (3) | −0.016 (3) |
C17 | 0.062 (4) | 0.068 (4) | 0.056 (3) | 0.001 (3) | −0.022 (3) | −0.010 (3) |
C18 | 0.052 (3) | 0.060 (4) | 0.061 (4) | 0.010 (3) | −0.015 (3) | −0.002 (3) |
N1 | 0.056 (3) | 0.068 (3) | 0.056 (3) | 0.009 (2) | −0.010 (2) | −0.018 (2) |
N2 | 0.050 (3) | 0.063 (3) | 0.052 (3) | 0.008 (2) | −0.009 (2) | −0.014 (2) |
N3 | 0.043 (2) | 0.057 (3) | 0.050 (2) | 0.013 (2) | −0.0163 (19) | −0.012 (2) |
O1 | 0.066 (2) | 0.075 (3) | 0.063 (2) | 0.028 (2) | −0.030 (2) | −0.015 (2) |
O2 | 0.060 (2) | 0.063 (2) | 0.056 (2) | 0.0254 (19) | −0.0179 (18) | −0.0149 (19) |
S1 | 0.0580 (9) | 0.0603 (9) | 0.0505 (8) | 0.0079 (7) | −0.0173 (7) | −0.0075 (7) |
Geometric parameters (Å, º) top
Br1—C16 | 1.897 (5) | C10—S1 | 1.711 (5) |
C1—C6 | 1.372 (9) | C11—O1 | 1.208 (5) |
C1—C2 | 1.391 (9) | C11—N3 | 1.352 (6) |
C1—H1 | 0.9300 | C11—C12 | 1.494 (6) |
C2—C3 | 1.358 (11) | C12—O2 | 1.407 (6) |
C2—H2 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.351 (11) | C12—H12B | 0.9700 |
C3—H3 | 0.9300 | C13—O2 | 1.366 (6) |
C4—C5 | 1.375 (9) | C13—C18 | 1.377 (7) |
C4—H4 | 0.9300 | C13—C14 | 1.390 (7) |
C5—C6 | 1.392 (8) | C14—C15 | 1.356 (7) |
C5—H5 | 0.9300 | C14—H14 | 0.9300 |
C6—C7 | 1.454 (7) | C15—C16 | 1.380 (8) |
C7—C8 | 1.327 (7) | C15—H15 | 0.9300 |
C7—H7 | 0.9300 | C16—C17 | 1.388 (8) |
C8—C9 | 1.446 (7) | C17—C18 | 1.376 (7) |
C8—H8 | 0.9300 | C17—H17 | 0.9300 |
C9—N1 | 1.310 (6) | C18—H18 | 0.9300 |
C9—S1 | 1.741 (5) | N1—N2 | 1.373 (5) |
C10—N2 | 1.303 (6) | N3—H3A | 0.8600 |
C10—N3 | 1.372 (6) | | |
| | | |
C6—C1—C2 | 121.0 (7) | N3—C11—C12 | 112.8 (4) |
C6—C1—H1 | 119.5 | O2—C12—C11 | 108.6 (4) |
C2—C1—H1 | 119.5 | O2—C12—H12A | 110.0 |
C3—C2—C1 | 119.6 (8) | C11—C12—H12A | 110.0 |
C3—C2—H2 | 120.2 | O2—C12—H12B | 110.0 |
C1—C2—H2 | 120.2 | C11—C12—H12B | 110.0 |
C4—C3—C2 | 120.9 (8) | H12A—C12—H12B | 108.4 |
C4—C3—H3 | 119.6 | O2—C13—C18 | 126.0 (5) |
C2—C3—H3 | 119.6 | O2—C13—C14 | 114.6 (4) |
C3—C4—C5 | 119.8 (8) | C18—C13—C14 | 119.3 (5) |
C3—C4—H4 | 120.1 | C15—C14—C13 | 120.8 (5) |
C5—C4—H4 | 120.1 | C15—C14—H14 | 119.6 |
C4—C5—C6 | 121.1 (8) | C13—C14—H14 | 119.6 |
C4—C5—H5 | 119.4 | C14—C15—C16 | 119.5 (5) |
C6—C5—H5 | 119.4 | C14—C15—H15 | 120.3 |
C1—C6—C5 | 117.6 (6) | C16—C15—H15 | 120.3 |
C1—C6—C7 | 123.5 (6) | C15—C16—C17 | 120.9 (5) |
C5—C6—C7 | 118.9 (6) | C15—C16—Br1 | 119.3 (4) |
C8—C7—C6 | 126.8 (6) | C17—C16—Br1 | 119.7 (4) |
C8—C7—H7 | 116.6 | C18—C17—C16 | 118.7 (5) |
C6—C7—H7 | 116.6 | C18—C17—H17 | 120.6 |
C7—C8—C9 | 125.5 (5) | C16—C17—H17 | 120.6 |
C7—C8—H8 | 117.3 | C17—C18—C13 | 120.7 (5) |
C9—C8—H8 | 117.3 | C17—C18—H18 | 119.6 |
N1—C9—C8 | 122.4 (5) | C13—C18—H18 | 119.6 |
N1—C9—S1 | 113.6 (4) | C9—N1—N2 | 112.2 (4) |
C8—C9—S1 | 123.9 (4) | C10—N2—N1 | 112.8 (4) |
N2—C10—N3 | 120.9 (4) | C11—N3—C10 | 124.6 (4) |
N2—C10—S1 | 114.6 (4) | C11—N3—H3A | 117.7 |
N3—C10—S1 | 124.5 (4) | C10—N3—H3A | 117.7 |
O1—C11—N3 | 122.2 (5) | C13—O2—C12 | 117.4 (4) |
O1—C11—C12 | 125.0 (4) | C10—S1—C9 | 86.8 (2) |
| | | |
C6—C1—C2—C3 | 0.5 (12) | Br1—C16—C17—C18 | −179.3 (4) |
C1—C2—C3—C4 | 0.7 (13) | C16—C17—C18—C13 | −0.8 (9) |
C2—C3—C4—C5 | −1.5 (14) | O2—C13—C18—C17 | 179.3 (5) |
C3—C4—C5—C6 | 1.1 (12) | C14—C13—C18—C17 | −1.0 (8) |
C2—C1—C6—C5 | −0.9 (10) | C8—C9—N1—N2 | 176.6 (5) |
C2—C1—C6—C7 | 179.3 (6) | S1—C9—N1—N2 | −0.5 (6) |
C4—C5—C6—C1 | 0.1 (10) | N3—C10—N2—N1 | 179.2 (4) |
C4—C5—C6—C7 | 179.9 (7) | S1—C10—N2—N1 | −1.7 (6) |
C1—C6—C7—C8 | −3.0 (10) | C9—N1—N2—C10 | 1.4 (6) |
C5—C6—C7—C8 | 177.2 (6) | O1—C11—N3—C10 | −3.6 (8) |
C6—C7—C8—C9 | 177.3 (5) | C12—C11—N3—C10 | 176.1 (5) |
C7—C8—C9—N1 | −175.0 (6) | N2—C10—N3—C11 | 177.2 (5) |
C7—C8—C9—S1 | 1.8 (9) | S1—C10—N3—C11 | −1.9 (7) |
O1—C11—C12—O2 | −4.8 (7) | C18—C13—O2—C12 | 3.0 (8) |
N3—C11—C12—O2 | 175.5 (4) | C14—C13—O2—C12 | −176.7 (5) |
O2—C13—C14—C15 | −178.9 (5) | C11—C12—O2—C13 | −172.2 (4) |
C18—C13—C14—C15 | 1.3 (8) | N2—C10—S1—C9 | 1.2 (4) |
C13—C14—C15—C16 | 0.3 (9) | N3—C10—S1—C9 | −179.7 (5) |
C14—C15—C16—C17 | −2.2 (9) | N1—C9—S1—C10 | −0.4 (4) |
C14—C15—C16—Br1 | 179.6 (4) | C8—C9—S1—C10 | −177.4 (5) |
C15—C16—C17—C18 | 2.5 (9) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···N2i | 0.86 | 2.02 | 2.869 (6) | 171 |
C14—H14···O1ii | 0.93 | 2.42 | 3.086 (6) | 128 |
Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+2, −y+1, −z+1. |