The title compound, C
18H
13BrO
2S, is chiral due to the twist of the naphthalene and thienyl rings about the chalcone backbone [dihedral angle = 17.75 (10)°]. There are weak C—H
O interactions which link the molecules into chains in the
b direction.
Supporting information
CCDC reference: 640321
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.066
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G
REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may
be needed to determine absolute structure
From the CIF: _diffrn_reflns_theta_max 30.74
From the CIF: _reflns_number_total 3626
Count of symmetry unique reflns 2486
Completeness (_total/calc) 145.86%
TEST3: Check Friedels for noncentro structure
Estimate of Friedel pairs measured 1140
Fraction of Friedel pairs measured 0.459
Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
0 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
0 ALERT type 3 Indicator that the structure quality may be low
3 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
1-(3-Bromo-2-thienyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one
top
Crystal data top
C18H13BrO2S | F(000) = 376 |
Mr = 373.25 | Dx = 1.619 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.0881 (1) Å | Cell parameters from 2083 reflections |
b = 11.0724 (2) Å | θ = 2.4–25.9° |
c = 16.9235 (4) Å | µ = 2.82 mm−1 |
β = 91.610 (1)° | T = 273 K |
V = 765.74 (3) Å3 | Plate, colourless |
Z = 2 | 0.54 × 0.34 × 0.13 mm |
Data collection top
Bruker APEXII CCD area-detector diffractometer | 3626 independent reflections |
Radiation source: fine-focus sealed tube | 2684 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 30.7°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −4→5 |
Tmin = 0.311, Tmax = 0.710 | k = −15→14 |
6193 measured reflections | l = −23→22 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.066 | w = 1/[σ2(Fo2)] |
S = 0.91 | (Δ/σ)max = 0.002 |
3626 reflections | Δρmax = 0.35 e Å−3 |
199 parameters | Δρmin = −0.33 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with how many Friedel pairs? |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.019 (7) |
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 | |
Br | 0.14625 (8) | 0.19412 (3) | 0.852141 (16) | 0.05635 (11) | |
S | 0.4221 (2) | −0.13604 (7) | 0.98139 (4) | 0.0485 (2) | |
O1 | 0.6514 (6) | −0.1929 (2) | 0.82834 (13) | 0.0623 (7) | |
O2 | −0.0060 (6) | −0.0195 (2) | 0.22920 (11) | 0.0515 (5) | |
C1 | 0.2645 (8) | −0.0289 (3) | 1.04068 (17) | 0.0506 (8) | |
H1A | 0.2399 | −0.0387 | 1.0948 | 0.061* | |
C2 | 0.1778 (8) | 0.0729 (3) | 1.00053 (16) | 0.0455 (7) | |
H2A | 0.0902 | 0.1414 | 1.0236 | 0.055* | |
C3 | 0.2377 (7) | 0.0610 (2) | 0.91995 (15) | 0.0367 (6) | |
C4 | 0.3701 (7) | −0.0474 (2) | 0.89847 (14) | 0.0357 (6) | |
C5 | 0.4745 (8) | −0.1042 (3) | 0.82394 (17) | 0.0433 (7) | |
C6 | 0.3537 (8) | −0.0554 (3) | 0.74752 (16) | 0.0464 (7) | |
H6A | 0.2170 | 0.0118 | 0.7466 | 0.056* | |
C7 | 0.4377 (7) | −0.1062 (3) | 0.67983 (16) | 0.0413 (7) | |
H7A | 0.5801 | −0.1716 | 0.6832 | 0.050* | |
C8 | 0.3267 (7) | −0.0686 (3) | 0.60043 (15) | 0.0378 (6) | |
C9 | 0.1356 (7) | 0.0358 (2) | 0.58718 (16) | 0.0384 (6) | |
H9A | 0.0728 | 0.0819 | 0.6301 | 0.046* | |
C10 | 0.0413 (8) | 0.0705 (3) | 0.51299 (16) | 0.0409 (6) | |
H10A | −0.0796 | 0.1411 | 0.5061 | 0.049* | |
C11 | 0.1233 (7) | 0.0013 (2) | 0.44556 (15) | 0.0347 (6) | |
C12 | 0.0193 (7) | 0.0340 (3) | 0.36817 (16) | 0.0395 (6) | |
H12A | −0.0975 | 0.1050 | 0.3595 | 0.047* | |
C13 | 0.0912 (7) | −0.0395 (3) | 0.30605 (15) | 0.0382 (6) | |
C14 | 0.2796 (8) | −0.1442 (3) | 0.31778 (16) | 0.0445 (7) | |
H14A | 0.3326 | −0.1918 | 0.2747 | 0.053* | |
C15 | 0.3854 (7) | −0.1766 (3) | 0.39178 (16) | 0.0411 (6) | |
H15A | 0.5090 | −0.2465 | 0.3987 | 0.049* | |
C16 | 0.3100 (7) | −0.1054 (2) | 0.45825 (15) | 0.0352 (6) | |
C17 | 0.4104 (7) | −0.1366 (3) | 0.53600 (15) | 0.0378 (6) | |
H17A | 0.5373 | −0.2055 | 0.5440 | 0.045* | |
C18 | −0.1878 (9) | 0.0897 (3) | 0.21245 (18) | 0.0547 (8) | |
H18A | −0.2398 | 0.0940 | 0.1569 | 0.082* | |
H18B | −0.0582 | 0.1584 | 0.2280 | 0.082* | |
H18C | −0.3864 | 0.0892 | 0.2414 | 0.082* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br | 0.0788 (2) | 0.04780 (16) | 0.04236 (16) | 0.0153 (2) | −0.00014 (13) | 0.00656 (16) |
S | 0.0670 (6) | 0.0434 (4) | 0.0349 (4) | 0.0023 (4) | −0.0040 (4) | 0.0051 (3) |
O1 | 0.0750 (18) | 0.0651 (15) | 0.0466 (13) | 0.0275 (14) | −0.0029 (12) | −0.0073 (11) |
O2 | 0.0628 (14) | 0.0625 (14) | 0.0290 (10) | −0.0028 (11) | −0.0004 (9) | −0.0020 (9) |
C1 | 0.069 (2) | 0.0532 (18) | 0.0298 (14) | −0.0062 (16) | 0.0051 (14) | −0.0018 (13) |
C2 | 0.055 (2) | 0.0479 (17) | 0.0344 (15) | −0.0027 (14) | 0.0067 (13) | −0.0071 (12) |
C3 | 0.0399 (16) | 0.0372 (14) | 0.0331 (14) | 0.0005 (13) | 0.0007 (11) | 0.0008 (11) |
C4 | 0.0394 (15) | 0.0385 (14) | 0.0290 (13) | −0.0017 (12) | −0.0034 (11) | 0.0015 (11) |
C5 | 0.0436 (17) | 0.0493 (18) | 0.0368 (15) | 0.0012 (14) | −0.0035 (12) | −0.0039 (12) |
C6 | 0.0555 (19) | 0.0497 (17) | 0.0338 (15) | 0.0038 (15) | −0.0038 (13) | −0.0016 (12) |
C7 | 0.0444 (17) | 0.0459 (17) | 0.0338 (14) | −0.0017 (13) | 0.0023 (12) | −0.0047 (11) |
C8 | 0.0424 (16) | 0.0403 (15) | 0.0309 (14) | −0.0068 (13) | 0.0013 (11) | −0.0025 (11) |
C9 | 0.0465 (18) | 0.0360 (14) | 0.0331 (14) | −0.0040 (13) | 0.0057 (12) | −0.0079 (10) |
C10 | 0.0501 (18) | 0.0348 (14) | 0.0379 (15) | 0.0012 (13) | 0.0011 (13) | −0.0066 (11) |
C11 | 0.0372 (15) | 0.0343 (13) | 0.0327 (14) | −0.0060 (12) | 0.0033 (11) | −0.0020 (10) |
C12 | 0.0428 (16) | 0.0397 (15) | 0.0361 (15) | −0.0018 (13) | 0.0039 (12) | 0.0007 (11) |
C13 | 0.0430 (16) | 0.0442 (15) | 0.0276 (13) | −0.0110 (13) | 0.0033 (11) | 0.0000 (11) |
C14 | 0.0541 (19) | 0.0465 (17) | 0.0334 (15) | −0.0109 (15) | 0.0102 (13) | −0.0144 (12) |
C15 | 0.0499 (18) | 0.0380 (14) | 0.0356 (15) | 0.0012 (13) | 0.0051 (13) | −0.0059 (11) |
C16 | 0.0352 (14) | 0.0366 (14) | 0.0341 (14) | −0.0059 (11) | 0.0053 (11) | −0.0054 (10) |
C17 | 0.0431 (16) | 0.0367 (14) | 0.0337 (14) | 0.0004 (13) | 0.0011 (12) | −0.0004 (11) |
C18 | 0.055 (2) | 0.068 (2) | 0.0404 (17) | −0.0064 (17) | −0.0055 (14) | 0.0096 (14) |
Geometric parameters (Å, º) top
Br—C3 | 1.899 (3) | C9—C10 | 1.359 (4) |
S—C1 | 1.692 (3) | C9—H9A | 0.9300 |
S—C4 | 1.721 (3) | C10—C11 | 1.422 (4) |
O1—C5 | 1.221 (3) | C10—H10A | 0.9300 |
O2—C13 | 1.367 (3) | C11—C12 | 1.413 (4) |
O2—C18 | 1.443 (4) | C11—C16 | 1.420 (4) |
C1—C2 | 1.358 (4) | C12—C13 | 1.368 (4) |
C1—H1A | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.398 (4) | C13—C14 | 1.403 (4) |
C2—H2A | 0.9300 | C14—C15 | 1.361 (4) |
C3—C4 | 1.370 (4) | C14—H14A | 0.9300 |
C4—C5 | 1.483 (4) | C15—C16 | 1.414 (4) |
C5—C6 | 1.474 (4) | C15—H15A | 0.9300 |
C6—C7 | 1.330 (4) | C16—C17 | 1.410 (4) |
C6—H6A | 0.9300 | C17—H17A | 0.9300 |
C7—C8 | 1.466 (4) | C18—H18A | 0.9600 |
C7—H7A | 0.9300 | C18—H18B | 0.9600 |
C8—C17 | 1.376 (4) | C18—H18C | 0.9600 |
C8—C9 | 1.410 (4) | | |
| | | |
C1—S—C4 | 92.48 (14) | C9—C10—H10A | 119.3 |
C13—O2—C18 | 117.2 (2) | C11—C10—H10A | 119.3 |
C2—C1—S | 112.5 (2) | C12—C11—C16 | 120.0 (2) |
C2—C1—H1A | 123.7 | C12—C11—C10 | 122.3 (3) |
S—C1—H1A | 123.7 | C16—C11—C10 | 117.7 (2) |
C1—C2—C3 | 111.1 (3) | C13—C12—C11 | 119.7 (3) |
C1—C2—H2A | 124.5 | C13—C12—H12A | 120.2 |
C3—C2—H2A | 124.5 | C11—C12—H12A | 120.2 |
C4—C3—C2 | 115.0 (2) | O2—C13—C12 | 124.9 (3) |
C4—C3—Br | 126.32 (19) | O2—C13—C14 | 114.4 (2) |
C2—C3—Br | 118.7 (2) | C12—C13—C14 | 120.8 (2) |
C3—C4—C5 | 136.3 (2) | C15—C14—C13 | 120.4 (3) |
C3—C4—S | 108.92 (19) | C15—C14—H14A | 119.8 |
C5—C4—S | 114.8 (2) | C13—C14—H14A | 119.8 |
O1—C5—C6 | 122.1 (3) | C14—C15—C16 | 121.0 (3) |
O1—C5—C4 | 118.3 (3) | C14—C15—H15A | 119.5 |
C6—C5—C4 | 119.6 (3) | C16—C15—H15A | 119.5 |
C7—C6—C5 | 120.8 (3) | C17—C16—C15 | 122.8 (3) |
C7—C6—H6A | 119.6 | C17—C16—C11 | 119.1 (2) |
C5—C6—H6A | 119.6 | C15—C16—C11 | 118.1 (2) |
C6—C7—C8 | 126.1 (3) | C8—C17—C16 | 122.2 (3) |
C6—C7—H7A | 117.0 | C8—C17—H17A | 118.9 |
C8—C7—H7A | 117.0 | C16—C17—H17A | 118.9 |
C17—C8—C9 | 118.1 (2) | O2—C18—H18A | 109.5 |
C17—C8—C7 | 119.6 (3) | O2—C18—H18B | 109.5 |
C9—C8—C7 | 122.3 (2) | H18A—C18—H18B | 109.5 |
C10—C9—C8 | 121.4 (2) | O2—C18—H18C | 109.5 |
C10—C9—H9A | 119.3 | H18A—C18—H18C | 109.5 |
C8—C9—H9A | 119.3 | H18B—C18—H18C | 109.5 |
C9—C10—C11 | 121.4 (3) | | |
| | | |
C4—S—C1—C2 | −1.0 (3) | C9—C10—C11—C12 | 178.1 (3) |
S—C1—C2—C3 | 1.0 (4) | C9—C10—C11—C16 | −0.4 (4) |
C1—C2—C3—C4 | −0.4 (4) | C16—C11—C12—C13 | 1.9 (4) |
C1—C2—C3—Br | −178.3 (2) | C10—C11—C12—C13 | −176.6 (3) |
C2—C3—C4—C5 | 179.6 (3) | C18—O2—C13—C12 | 2.3 (4) |
Br—C3—C4—C5 | −2.6 (5) | C18—O2—C13—C14 | −177.2 (3) |
C2—C3—C4—S | −0.3 (3) | C11—C12—C13—O2 | 177.6 (2) |
Br—C3—C4—S | 177.43 (16) | C11—C12—C13—C14 | −2.9 (4) |
C1—S—C4—C3 | 0.7 (2) | O2—C13—C14—C15 | −178.3 (3) |
C1—S—C4—C5 | −179.2 (2) | C12—C13—C14—C15 | 2.1 (4) |
C3—C4—C5—O1 | 163.7 (3) | C13—C14—C15—C16 | −0.4 (5) |
S—C4—C5—O1 | −16.4 (4) | C14—C15—C16—C17 | 179.0 (3) |
C3—C4—C5—C6 | −18.5 (5) | C14—C15—C16—C11 | −0.6 (4) |
S—C4—C5—C6 | 161.4 (2) | C12—C11—C16—C17 | −179.8 (3) |
O1—C5—C6—C7 | −0.8 (5) | C10—C11—C16—C17 | −1.2 (4) |
C4—C5—C6—C7 | −178.5 (3) | C12—C11—C16—C15 | −0.2 (4) |
C5—C6—C7—C8 | 178.1 (3) | C10—C11—C16—C15 | 178.3 (3) |
C6—C7—C8—C17 | −174.1 (3) | C9—C8—C17—C16 | −0.3 (4) |
C6—C7—C8—C9 | 6.0 (5) | C7—C8—C17—C16 | 179.8 (2) |
C17—C8—C9—C10 | −1.4 (4) | C15—C16—C17—C8 | −177.9 (3) |
C7—C8—C9—C10 | 178.5 (3) | C11—C16—C17—C8 | 1.6 (4) |
C8—C9—C10—C11 | 1.8 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18B···O1i | 0.96 | 2.54 | 3.342 (4) | 141 |
Symmetry code: (i) −x+1, y+1/2, −z+1. |