The title compound, C
17H
16BrNO, adopts an
E configuration. The dihedral angle between the two benzene rings is 49.17 (13)°. Intramolecular C—H
O weak interactions are present in the crystal structure. The molecules are arranged in double layers parallel to the
bc plane. These double layers are stacked in an anti-parallel fashion along the
a axis. The crystal structure is stabilized by intramolecular C—H
O weak interactions. C—H
π interaction are also observed in the crystal packing.
Supporting information
CCDC reference: 643092
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C)= 0.004 Å
- R factor = 0.046
- wR factor = 0.134
- Data-to-parameter ratio = 22.5
checkCIF/PLATON results
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No errors found in this datablock
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).
1-(3-Bromophenyl)-3-(4-dimethylamino)prop-2-en-1-one
top
Crystal data top
C17H16BrNO | F(000) = 1344 |
Mr = 330.21 | Dx = 1.552 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4122 reflections |
a = 13.9586 (5) Å | θ = 1.2–30.0° |
b = 6.0703 (2) Å | µ = 2.90 mm−1 |
c = 33.3498 (12) Å | T = 100 K |
V = 2825.82 (17) Å3 | Plate, yellow |
Z = 8 | 0.46 × 0.25 × 0.07 mm |
Data collection top
Bruker SMART APEX2 CCD area-detector diffractometer | 4122 independent reflections |
Radiation source: fine-focus sealed tube | 3031 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.092 |
Detector resolution: 8.33 pixels mm-1 | θmax = 30.0°, θmin = 1.2° |
ω scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −8→8 |
Tmin = 0.349, Tmax = 0.823 | l = −45→46 |
69164 measured reflections | |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0604P)2 + 3.4713P] where P = (Fo2 + 2Fc2)/3 |
4122 reflections | (Δ/σ)max < 0.001 |
183 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.53 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 | 0.33780 (2) | 0.69579 (5) | 0.516216 (9) | 0.02250 (12) | |
O1 | 0.35265 (16) | 0.6151 (4) | 0.35620 (7) | 0.0226 (5) | |
N1 | 0.3962 (2) | 1.2966 (4) | 0.13491 (8) | 0.0221 (6) | |
C1 | 0.3430 (2) | 0.7901 (5) | 0.43261 (9) | 0.0172 (6) | |
H1A | 0.3189 | 0.6483 | 0.4295 | 0.021* | |
C2 | 0.3604 (2) | 0.8767 (5) | 0.47052 (10) | 0.0185 (6) | |
C3 | 0.3952 (2) | 1.0874 (5) | 0.47612 (9) | 0.0204 (6) | |
H3A | 0.4063 | 1.1411 | 0.5018 | 0.024* | |
C4 | 0.4132 (2) | 1.2172 (5) | 0.44290 (10) | 0.0216 (6) | |
H4A | 0.4370 | 1.3591 | 0.4463 | 0.026* | |
C5 | 0.3960 (2) | 1.1373 (5) | 0.40427 (10) | 0.0203 (6) | |
H5A | 0.4066 | 1.2270 | 0.3821 | 0.024* | |
C6 | 0.3629 (2) | 0.9230 (5) | 0.39915 (9) | 0.0176 (6) | |
C7 | 0.3555 (2) | 0.8169 (5) | 0.35851 (10) | 0.0188 (6) | |
C8 | 0.3555 (2) | 0.9583 (6) | 0.32257 (10) | 0.0211 (6) | |
H8A | 0.3376 | 1.1055 | 0.3246 | 0.025* | |
C9 | 0.3814 (2) | 0.8742 (5) | 0.28690 (9) | 0.0194 (6) | |
H9A | 0.3995 | 0.7267 | 0.2868 | 0.023* | |
C10 | 0.3844 (2) | 0.9876 (5) | 0.24851 (9) | 0.0181 (6) | |
C11 | 0.3438 (2) | 1.1959 (5) | 0.24219 (10) | 0.0187 (6) | |
H11A | 0.3149 | 1.2684 | 0.2636 | 0.022* | |
C12 | 0.3458 (2) | 1.2964 (5) | 0.20489 (10) | 0.0195 (6) | |
H12A | 0.3169 | 1.4331 | 0.2015 | 0.023* | |
C13 | 0.3910 (2) | 1.1942 (5) | 0.17201 (9) | 0.0180 (6) | |
C14 | 0.4320 (2) | 0.9856 (5) | 0.17856 (9) | 0.0199 (6) | |
H14A | 0.4621 | 0.9134 | 0.1574 | 0.024* | |
C15 | 0.4284 (2) | 0.8862 (5) | 0.21574 (9) | 0.0194 (6) | |
H15A | 0.4560 | 0.7480 | 0.2191 | 0.023* | |
C16 | 0.4216 (3) | 1.1670 (6) | 0.09993 (10) | 0.0249 (7) | |
H16A | 0.4820 | 1.0958 | 0.1044 | 0.037* | |
H16B | 0.4263 | 1.2618 | 0.0770 | 0.037* | |
H16C | 0.3731 | 1.0577 | 0.0952 | 0.037* | |
C17 | 0.3361 (3) | 1.4866 (6) | 0.12730 (11) | 0.0288 (8) | |
H17A | 0.3478 | 1.5965 | 0.1474 | 0.043* | |
H17B | 0.2700 | 1.4433 | 0.1281 | 0.043* | |
H17C | 0.3508 | 1.5459 | 0.1013 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02505 (19) | 0.02394 (18) | 0.01852 (17) | −0.00279 (13) | −0.00138 (12) | 0.00413 (12) |
O1 | 0.0254 (12) | 0.0207 (11) | 0.0218 (12) | −0.0010 (9) | 0.0004 (9) | 0.0019 (9) |
N1 | 0.0224 (14) | 0.0241 (13) | 0.0196 (13) | 0.0022 (11) | 0.0008 (11) | 0.0015 (11) |
C1 | 0.0156 (14) | 0.0155 (13) | 0.0205 (15) | 0.0012 (12) | 0.0005 (11) | 0.0005 (11) |
C2 | 0.0150 (15) | 0.0206 (14) | 0.0199 (15) | −0.0004 (11) | 0.0000 (11) | 0.0027 (12) |
C3 | 0.0183 (15) | 0.0222 (15) | 0.0206 (16) | 0.0011 (12) | −0.0001 (11) | −0.0005 (12) |
C4 | 0.0172 (15) | 0.0176 (14) | 0.0301 (17) | −0.0011 (12) | 0.0005 (13) | 0.0018 (13) |
C5 | 0.0164 (15) | 0.0195 (14) | 0.0250 (16) | −0.0004 (11) | 0.0015 (12) | 0.0039 (12) |
C6 | 0.0147 (14) | 0.0176 (14) | 0.0207 (15) | 0.0026 (11) | −0.0007 (11) | 0.0036 (12) |
C7 | 0.0127 (14) | 0.0242 (15) | 0.0195 (15) | 0.0013 (12) | 0.0019 (11) | 0.0029 (12) |
C8 | 0.0207 (16) | 0.0215 (15) | 0.0212 (16) | 0.0019 (12) | −0.0008 (12) | 0.0022 (12) |
C9 | 0.0151 (15) | 0.0198 (14) | 0.0234 (16) | 0.0017 (11) | −0.0025 (12) | 0.0017 (12) |
C10 | 0.0154 (14) | 0.0185 (14) | 0.0204 (15) | −0.0007 (11) | −0.0013 (12) | 0.0006 (12) |
C11 | 0.0171 (15) | 0.0194 (13) | 0.0196 (14) | 0.0019 (12) | 0.0012 (12) | −0.0010 (12) |
C12 | 0.0189 (15) | 0.0189 (14) | 0.0206 (15) | 0.0021 (12) | −0.0014 (12) | 0.0002 (12) |
C13 | 0.0121 (14) | 0.0216 (14) | 0.0202 (15) | −0.0017 (11) | −0.0009 (11) | 0.0004 (12) |
C14 | 0.0183 (15) | 0.0198 (14) | 0.0215 (15) | −0.0004 (12) | 0.0011 (12) | −0.0046 (12) |
C15 | 0.0167 (15) | 0.0176 (14) | 0.0238 (16) | 0.0005 (11) | −0.0031 (12) | −0.0002 (12) |
C16 | 0.0232 (17) | 0.0306 (17) | 0.0208 (16) | −0.0038 (13) | 0.0037 (13) | −0.0005 (13) |
C17 | 0.037 (2) | 0.0246 (16) | 0.0248 (17) | 0.0028 (15) | −0.0018 (15) | 0.0043 (14) |
Geometric parameters (Å, º) top
Br1—C2 | 1.905 (3) | C9—C10 | 1.454 (4) |
O1—C7 | 1.228 (4) | C9—H9A | 0.9300 |
N1—C13 | 1.387 (4) | C10—C15 | 1.397 (4) |
N1—C17 | 1.448 (4) | C10—C11 | 1.401 (4) |
N1—C16 | 1.451 (4) | C11—C12 | 1.386 (4) |
C1—C2 | 1.391 (4) | C11—H11A | 0.9300 |
C1—C6 | 1.405 (4) | C12—C13 | 1.409 (4) |
C1—H1A | 0.9300 | C12—H12A | 0.9300 |
C2—C3 | 1.381 (5) | C13—C14 | 1.406 (4) |
C3—C4 | 1.383 (4) | C14—C15 | 1.380 (4) |
C3—H3A | 0.9300 | C14—H14A | 0.9300 |
C4—C5 | 1.397 (4) | C15—H15A | 0.9300 |
C4—H4A | 0.9300 | C16—H16A | 0.9600 |
C5—C6 | 1.391 (4) | C16—H16B | 0.9600 |
C5—H5A | 0.9300 | C16—H16C | 0.9600 |
C6—C7 | 1.504 (4) | C17—H17A | 0.9600 |
C7—C8 | 1.474 (4) | C17—H17B | 0.9600 |
C8—C9 | 1.344 (4) | C17—H17C | 0.9600 |
C8—H8A | 0.9300 | | |
| | | |
C13—N1—C17 | 118.9 (3) | C15—C10—C11 | 117.2 (3) |
C13—N1—C16 | 119.1 (3) | C15—C10—C9 | 119.5 (3) |
C17—N1—C16 | 115.6 (3) | C11—C10—C9 | 123.2 (3) |
C2—C1—C6 | 118.1 (3) | C12—C11—C10 | 121.6 (3) |
C2—C1—H1A | 121.0 | C12—C11—H11A | 119.2 |
C6—C1—H1A | 121.0 | C10—C11—H11A | 119.2 |
C3—C2—C1 | 122.3 (3) | C11—C12—C13 | 120.9 (3) |
C3—C2—Br1 | 119.0 (2) | C11—C12—H12A | 119.5 |
C1—C2—Br1 | 118.7 (2) | C13—C12—H12A | 119.5 |
C2—C3—C4 | 118.9 (3) | N1—C13—C14 | 121.4 (3) |
C2—C3—H3A | 120.5 | N1—C13—C12 | 121.4 (3) |
C4—C3—H3A | 120.5 | C14—C13—C12 | 117.2 (3) |
C3—C4—C5 | 120.6 (3) | C15—C14—C13 | 121.2 (3) |
C3—C4—H4A | 119.7 | C15—C14—H14A | 119.4 |
C5—C4—H4A | 119.7 | C13—C14—H14A | 119.4 |
C6—C5—C4 | 119.7 (3) | C14—C15—C10 | 121.8 (3) |
C6—C5—H5A | 120.2 | C14—C15—H15A | 119.1 |
C4—C5—H5A | 120.2 | C10—C15—H15A | 119.1 |
C5—C6—C1 | 120.3 (3) | N1—C16—H16A | 109.5 |
C5—C6—C7 | 122.3 (3) | N1—C16—H16B | 109.5 |
C1—C6—C7 | 117.1 (3) | H16A—C16—H16B | 109.5 |
O1—C7—C8 | 122.0 (3) | N1—C16—H16C | 109.5 |
O1—C7—C6 | 119.1 (3) | H16A—C16—H16C | 109.5 |
C8—C7—C6 | 118.9 (3) | H16B—C16—H16C | 109.5 |
C9—C8—C7 | 119.9 (3) | N1—C17—H17A | 109.5 |
C9—C8—H8A | 120.1 | N1—C17—H17B | 109.5 |
C7—C8—H8A | 120.1 | H17A—C17—H17B | 109.5 |
C8—C9—C10 | 127.3 (3) | N1—C17—H17C | 109.5 |
C8—C9—H9A | 116.3 | H17A—C17—H17C | 109.5 |
C10—C9—H9A | 116.3 | H17B—C17—H17C | 109.5 |
| | | |
C6—C1—C2—C3 | 0.7 (5) | C8—C9—C10—C15 | 169.2 (3) |
C6—C1—C2—Br1 | −178.0 (2) | C8—C9—C10—C11 | −11.7 (5) |
C1—C2—C3—C4 | 0.2 (5) | C15—C10—C11—C12 | 0.9 (5) |
Br1—C2—C3—C4 | 178.9 (2) | C9—C10—C11—C12 | −178.2 (3) |
C2—C3—C4—C5 | 0.4 (5) | C10—C11—C12—C13 | −1.5 (5) |
C3—C4—C5—C6 | −1.8 (5) | C17—N1—C13—C14 | 166.9 (3) |
C4—C5—C6—C1 | 2.7 (5) | C16—N1—C13—C14 | 16.1 (4) |
C4—C5—C6—C7 | −171.7 (3) | C17—N1—C13—C12 | −14.1 (4) |
C2—C1—C6—C5 | −2.1 (4) | C16—N1—C13—C12 | −165.0 (3) |
C2—C1—C6—C7 | 172.5 (3) | C11—C12—C13—N1 | −177.8 (3) |
C5—C6—C7—O1 | 159.5 (3) | C11—C12—C13—C14 | 1.2 (4) |
C1—C6—C7—O1 | −15.0 (4) | N1—C13—C14—C15 | 178.7 (3) |
C5—C6—C7—C8 | −18.3 (4) | C12—C13—C14—C15 | −0.4 (4) |
C1—C6—C7—C8 | 167.2 (3) | C13—C14—C15—C10 | −0.2 (5) |
O1—C7—C8—C9 | −20.3 (5) | C11—C10—C15—C14 | −0.1 (5) |
C6—C7—C8—C9 | 157.4 (3) | C9—C10—C15—C14 | 179.1 (3) |
C7—C8—C9—C10 | 179.1 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1 | 0.93 | 2.50 | 2.824 (4) | 101 |
C1—H1A···Cg1i | 0.93 | 2.90 | 3.546 (3) | 128 |
C9—H9A···Cg2ii | 0.93 | 3.09 | 3.656 (3) | 121 |
C12—H12A···Cg2iii | 0.93 | 3.03 | 3.721 (3) | 133 |
C16—H16B···Cg1iv | 0.96 | 3.14 | 3.684 (4) | 118 |
Symmetry codes: (i) x, −y−3/2, z−1/2; (ii) x+3/2, −y−1/2, −z; (iii) x, −y−1/2, z−1/2; (iv) x+3/2, −y+1/2, −z. |