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The title compound, C17H16BrNO, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701118X/sg2150sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701118X/sg2150Isup2.hkl
Contains datablock I

CCDC reference: 643092

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](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

Computing details top

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
C17H16BrNOF(000) = 1344
Mr = 330.21Dx = 1.552 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4122 reflections
a = 13.9586 (5) Åθ = 1.2–30.0°
b = 6.0703 (2) ŵ = 2.90 mm1
c = 33.3498 (12) ÅT = 100 K
V = 2825.82 (17) Å3Plate, yellow
Z = 80.46 × 0.25 × 0.07 mm
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
4122 independent reflections
Radiation source: fine-focus sealed tube3031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.092
Detector resolution: 8.33 pixels mm-1θmax = 30.0°, θmin = 1.2°
ω scansh = 1919
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 88
Tmin = 0.349, Tmax = 0.823l = 4546
69164 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134H-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 parametersΔρmax = 0.92 e Å3
0 restraintsΔρmin = 0.53 e Å3
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
xyzUiso*/Ueq
Br10.33780 (2)0.69579 (5)0.516216 (9)0.02250 (12)
O10.35265 (16)0.6151 (4)0.35620 (7)0.0226 (5)
N10.3962 (2)1.2966 (4)0.13491 (8)0.0221 (6)
C10.3430 (2)0.7901 (5)0.43261 (9)0.0172 (6)
H1A0.31890.64830.42950.021*
C20.3604 (2)0.8767 (5)0.47052 (10)0.0185 (6)
C30.3952 (2)1.0874 (5)0.47612 (9)0.0204 (6)
H3A0.40631.14110.50180.024*
C40.4132 (2)1.2172 (5)0.44290 (10)0.0216 (6)
H4A0.43701.35910.44630.026*
C50.3960 (2)1.1373 (5)0.40427 (10)0.0203 (6)
H5A0.40661.22700.38210.024*
C60.3629 (2)0.9230 (5)0.39915 (9)0.0176 (6)
C70.3555 (2)0.8169 (5)0.35851 (10)0.0188 (6)
C80.3555 (2)0.9583 (6)0.32257 (10)0.0211 (6)
H8A0.33761.10550.32460.025*
C90.3814 (2)0.8742 (5)0.28690 (9)0.0194 (6)
H9A0.39950.72670.28680.023*
C100.3844 (2)0.9876 (5)0.24851 (9)0.0181 (6)
C110.3438 (2)1.1959 (5)0.24219 (10)0.0187 (6)
H11A0.31491.26840.26360.022*
C120.3458 (2)1.2964 (5)0.20489 (10)0.0195 (6)
H12A0.31691.43310.20150.023*
C130.3910 (2)1.1942 (5)0.17201 (9)0.0180 (6)
C140.4320 (2)0.9856 (5)0.17856 (9)0.0199 (6)
H14A0.46210.91340.15740.024*
C150.4284 (2)0.8862 (5)0.21574 (9)0.0194 (6)
H15A0.45600.74800.21910.023*
C160.4216 (3)1.1670 (6)0.09993 (10)0.0249 (7)
H16A0.48201.09580.10440.037*
H16B0.42631.26180.07700.037*
H16C0.37311.05770.09520.037*
C170.3361 (3)1.4866 (6)0.12730 (11)0.0288 (8)
H17A0.34781.59650.14740.043*
H17B0.27001.44330.12810.043*
H17C0.35081.54590.10130.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02505 (19)0.02394 (18)0.01852 (17)0.00279 (13)0.00138 (12)0.00413 (12)
O10.0254 (12)0.0207 (11)0.0218 (12)0.0010 (9)0.0004 (9)0.0019 (9)
N10.0224 (14)0.0241 (13)0.0196 (13)0.0022 (11)0.0008 (11)0.0015 (11)
C10.0156 (14)0.0155 (13)0.0205 (15)0.0012 (12)0.0005 (11)0.0005 (11)
C20.0150 (15)0.0206 (14)0.0199 (15)0.0004 (11)0.0000 (11)0.0027 (12)
C30.0183 (15)0.0222 (15)0.0206 (16)0.0011 (12)0.0001 (11)0.0005 (12)
C40.0172 (15)0.0176 (14)0.0301 (17)0.0011 (12)0.0005 (13)0.0018 (13)
C50.0164 (15)0.0195 (14)0.0250 (16)0.0004 (11)0.0015 (12)0.0039 (12)
C60.0147 (14)0.0176 (14)0.0207 (15)0.0026 (11)0.0007 (11)0.0036 (12)
C70.0127 (14)0.0242 (15)0.0195 (15)0.0013 (12)0.0019 (11)0.0029 (12)
C80.0207 (16)0.0215 (15)0.0212 (16)0.0019 (12)0.0008 (12)0.0022 (12)
C90.0151 (15)0.0198 (14)0.0234 (16)0.0017 (11)0.0025 (12)0.0017 (12)
C100.0154 (14)0.0185 (14)0.0204 (15)0.0007 (11)0.0013 (12)0.0006 (12)
C110.0171 (15)0.0194 (13)0.0196 (14)0.0019 (12)0.0012 (12)0.0010 (12)
C120.0189 (15)0.0189 (14)0.0206 (15)0.0021 (12)0.0014 (12)0.0002 (12)
C130.0121 (14)0.0216 (14)0.0202 (15)0.0017 (11)0.0009 (11)0.0004 (12)
C140.0183 (15)0.0198 (14)0.0215 (15)0.0004 (12)0.0011 (12)0.0046 (12)
C150.0167 (15)0.0176 (14)0.0238 (16)0.0005 (11)0.0031 (12)0.0002 (12)
C160.0232 (17)0.0306 (17)0.0208 (16)0.0038 (13)0.0037 (13)0.0005 (13)
C170.037 (2)0.0246 (16)0.0248 (17)0.0028 (15)0.0018 (15)0.0043 (14)
Geometric parameters (Å, º) top
Br1—C21.905 (3)C9—C101.454 (4)
O1—C71.228 (4)C9—H9A0.9300
N1—C131.387 (4)C10—C151.397 (4)
N1—C171.448 (4)C10—C111.401 (4)
N1—C161.451 (4)C11—C121.386 (4)
C1—C21.391 (4)C11—H11A0.9300
C1—C61.405 (4)C12—C131.409 (4)
C1—H1A0.9300C12—H12A0.9300
C2—C31.381 (5)C13—C141.406 (4)
C3—C41.383 (4)C14—C151.380 (4)
C3—H3A0.9300C14—H14A0.9300
C4—C51.397 (4)C15—H15A0.9300
C4—H4A0.9300C16—H16A0.9600
C5—C61.391 (4)C16—H16B0.9600
C5—H5A0.9300C16—H16C0.9600
C6—C71.504 (4)C17—H17A0.9600
C7—C81.474 (4)C17—H17B0.9600
C8—C91.344 (4)C17—H17C0.9600
C8—H8A0.9300
C13—N1—C17118.9 (3)C15—C10—C11117.2 (3)
C13—N1—C16119.1 (3)C15—C10—C9119.5 (3)
C17—N1—C16115.6 (3)C11—C10—C9123.2 (3)
C2—C1—C6118.1 (3)C12—C11—C10121.6 (3)
C2—C1—H1A121.0C12—C11—H11A119.2
C6—C1—H1A121.0C10—C11—H11A119.2
C3—C2—C1122.3 (3)C11—C12—C13120.9 (3)
C3—C2—Br1119.0 (2)C11—C12—H12A119.5
C1—C2—Br1118.7 (2)C13—C12—H12A119.5
C2—C3—C4118.9 (3)N1—C13—C14121.4 (3)
C2—C3—H3A120.5N1—C13—C12121.4 (3)
C4—C3—H3A120.5C14—C13—C12117.2 (3)
C3—C4—C5120.6 (3)C15—C14—C13121.2 (3)
C3—C4—H4A119.7C15—C14—H14A119.4
C5—C4—H4A119.7C13—C14—H14A119.4
C6—C5—C4119.7 (3)C14—C15—C10121.8 (3)
C6—C5—H5A120.2C14—C15—H15A119.1
C4—C5—H5A120.2C10—C15—H15A119.1
C5—C6—C1120.3 (3)N1—C16—H16A109.5
C5—C6—C7122.3 (3)N1—C16—H16B109.5
C1—C6—C7117.1 (3)H16A—C16—H16B109.5
O1—C7—C8122.0 (3)N1—C16—H16C109.5
O1—C7—C6119.1 (3)H16A—C16—H16C109.5
C8—C7—C6118.9 (3)H16B—C16—H16C109.5
C9—C8—C7119.9 (3)N1—C17—H17A109.5
C9—C8—H8A120.1N1—C17—H17B109.5
C7—C8—H8A120.1H17A—C17—H17B109.5
C8—C9—C10127.3 (3)N1—C17—H17C109.5
C8—C9—H9A116.3H17A—C17—H17C109.5
C10—C9—H9A116.3H17B—C17—H17C109.5
C6—C1—C2—C30.7 (5)C8—C9—C10—C15169.2 (3)
C6—C1—C2—Br1178.0 (2)C8—C9—C10—C1111.7 (5)
C1—C2—C3—C40.2 (5)C15—C10—C11—C120.9 (5)
Br1—C2—C3—C4178.9 (2)C9—C10—C11—C12178.2 (3)
C2—C3—C4—C50.4 (5)C10—C11—C12—C131.5 (5)
C3—C4—C5—C61.8 (5)C17—N1—C13—C14166.9 (3)
C4—C5—C6—C12.7 (5)C16—N1—C13—C1416.1 (4)
C4—C5—C6—C7171.7 (3)C17—N1—C13—C1214.1 (4)
C2—C1—C6—C52.1 (4)C16—N1—C13—C12165.0 (3)
C2—C1—C6—C7172.5 (3)C11—C12—C13—N1177.8 (3)
C5—C6—C7—O1159.5 (3)C11—C12—C13—C141.2 (4)
C1—C6—C7—O115.0 (4)N1—C13—C14—C15178.7 (3)
C5—C6—C7—C818.3 (4)C12—C13—C14—C150.4 (4)
C1—C6—C7—C8167.2 (3)C13—C14—C15—C100.2 (5)
O1—C7—C8—C920.3 (5)C11—C10—C15—C140.1 (5)
C6—C7—C8—C9157.4 (3)C9—C10—C15—C14179.1 (3)
C7—C8—C9—C10179.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O10.932.502.824 (4)101
C1—H1A···Cg1i0.932.903.546 (3)128
C9—H9A···Cg2ii0.933.093.656 (3)121
C12—H12A···Cg2iii0.933.033.721 (3)133
C16—H16B···Cg1iv0.963.143.684 (4)118
Symmetry codes: (i) x, y3/2, z1/2; (ii) x+3/2, y1/2, z; (iii) x, y1/2, z1/2; (iv) x+3/2, y+1/2, z.
 

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