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In the title compound, C16H13BrO2, the dihedral angle between the aromatic rings is 41.34 (6)°. The mol­ecules (via two C—H...O inter­molecular inter­actions) form chains along the a axis that stack into layers parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039778/gg2012sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039778/gg2012Isup2.hkl
Contains datablock I

CCDC reference: 627666

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.023
  • wR factor = 0.067
  • Data-to-parameter ratio = 39.4

checkCIF/PLATON results

No syntax errors found



Alert level A CELLV02_ALERT_1_A The supplied cell volume s.u. differs from that calculated from the cell parameter s.u.'s by > 8 Calculated cell volume su = 19.84 Cell volume su given = 10.00
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.80 PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.802 Tmax scaled 0.314 Tmin scaled 0.296 REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 37.50 From the CIF: _reflns_number_total 6812 Count of symmetry unique reflns 3831 Completeness (_total/calc) 177.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2981 Fraction of Friedel pairs measured 0.778 Are heavy atom types Z>Si present yes
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL024_ALERT_1_A The number of authors is greater than 5. Please specify the role of each of the co-authors for your paper.
Author Response: H.K. Fun and I.A. Razak are supervisors of M.M. Rosli whereas S.M. Dharmaprakash is the supervisor of P.S. Patil and Vedavati G. Puranik in this collaborative publication. Mangalore University and National Chemical Laboratory, India is involved in the extraction and synthesis of the title compound and USM is involved in the structure determination. All parties are involved in writing up the manuscript.

1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing

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, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

3-(3-Bromophenyl)-1-(4-meyhoxyphenyl)prop-2-en-1-one top
Crystal data top
C16H13BrO2F(000) = 320
Mr = 317.17Dx = 1.610 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 7113 reflections
a = 10.2917 (1) Åθ = 2.7–37.5°
b = 3.8970 (1) ŵ = 3.14 mm1
c = 17.0919 (2) ÅT = 100 K
β = 107.313 (1)°Block, yellow
V = 654.46 (1) Å30.40 × 0.38 × 0.37 mm
Z = 2
Data collection top
Bruker SMART APEX2 CCD area-detector
diffractometer
6812 independent reflections
Radiation source: fine-focus sealed tube6194 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
Detector resolution: 8.33 pixels mm-1θmax = 37.5°, θmin = 1.3°
ω scansh = 1717
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 66
Tmin = 0.369, Tmax = 0.391l = 2928
31059 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.067 w = 1/[σ2(Fo2) + (0.0342P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max = 0.001
6812 reflectionsΔρmax = 0.64 e Å3
173 parametersΔρmin = 0.37 e Å3
1 restraintAbsolute structure: Flack (1983), 2981 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.008 (5)
Special details top

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br10.357551 (11)0.79782 (5)0.574543 (6)0.02143 (3)
O10.28008 (10)0.9906 (3)0.10248 (7)0.0264 (2)
O20.91154 (9)1.0452 (3)0.14142 (6)0.02069 (17)
C10.63215 (12)0.8777 (3)0.22358 (8)0.0174 (2)
H1A0.62000.78190.27070.021*
C20.76174 (12)0.9006 (3)0.21518 (8)0.0187 (2)
H2A0.83620.81970.25660.022*
C30.78077 (11)1.0448 (3)0.14462 (8)0.01631 (18)
C40.67021 (12)1.1740 (3)0.08284 (8)0.01701 (18)
H4A0.68291.27560.03640.020*
C50.54069 (11)1.1481 (3)0.09195 (7)0.01675 (19)
H5A0.46661.23260.05080.020*
C60.51905 (11)0.9985 (3)0.16124 (7)0.01585 (18)
C70.37727 (12)0.9554 (3)0.16440 (8)0.0184 (2)
C80.35654 (12)0.8662 (3)0.24421 (8)0.0190 (2)
H8A0.42590.90890.29230.023*
C90.24013 (12)0.7255 (3)0.24851 (8)0.0180 (2)
H9A0.17450.67830.19900.022*
C100.20588 (11)0.6387 (3)0.32349 (8)0.01608 (18)
C110.08441 (11)0.4626 (3)0.31654 (8)0.01783 (19)
H11A0.02930.39630.26510.021*
C120.04532 (12)0.3856 (3)0.38569 (9)0.0199 (2)
H12A0.03590.26970.38010.024*
C130.12654 (12)0.4804 (3)0.46296 (8)0.0186 (2)
H13A0.10090.42900.50940.022*
C140.24757 (11)0.6546 (3)0.46931 (7)0.01674 (19)
C150.28875 (11)0.7349 (3)0.40159 (7)0.0165 (2)
H15A0.37010.85080.40760.020*
C160.93644 (13)1.1917 (4)0.07045 (9)0.0230 (2)
H16A1.03201.18020.07600.034*
H16B0.90751.42700.06510.034*
H16C0.88651.06620.02260.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.02897 (5)0.01920 (5)0.01360 (5)0.00116 (6)0.00248 (3)0.00054 (5)
O10.0187 (4)0.0426 (6)0.0166 (4)0.0007 (4)0.0033 (3)0.0031 (4)
O20.0161 (3)0.0288 (5)0.0178 (4)0.0003 (3)0.0060 (3)0.0010 (3)
C10.0185 (4)0.0204 (5)0.0129 (4)0.0011 (3)0.0042 (3)0.0010 (3)
C20.0182 (4)0.0221 (5)0.0146 (5)0.0018 (4)0.0033 (3)0.0012 (4)
C30.0172 (4)0.0177 (4)0.0142 (5)0.0004 (3)0.0049 (3)0.0018 (4)
C40.0189 (4)0.0184 (4)0.0136 (5)0.0011 (4)0.0046 (3)0.0003 (4)
C50.0175 (4)0.0185 (5)0.0131 (5)0.0005 (4)0.0028 (3)0.0006 (4)
C60.0168 (4)0.0179 (4)0.0127 (5)0.0004 (3)0.0042 (3)0.0008 (4)
C70.0174 (4)0.0227 (5)0.0154 (5)0.0007 (4)0.0055 (4)0.0001 (4)
C80.0197 (4)0.0241 (6)0.0138 (5)0.0032 (4)0.0057 (3)0.0011 (4)
C90.0185 (4)0.0216 (6)0.0143 (5)0.0009 (3)0.0055 (3)0.0000 (3)
C100.0154 (4)0.0179 (5)0.0150 (5)0.0003 (3)0.0045 (3)0.0002 (4)
C110.0161 (4)0.0191 (5)0.0176 (5)0.0004 (4)0.0039 (4)0.0001 (4)
C120.0180 (4)0.0212 (5)0.0214 (6)0.0010 (3)0.0070 (4)0.0016 (4)
C130.0203 (4)0.0188 (5)0.0189 (5)0.0019 (4)0.0089 (4)0.0027 (4)
C140.0193 (4)0.0158 (5)0.0146 (5)0.0023 (4)0.0042 (3)0.0004 (4)
C150.0167 (4)0.0183 (6)0.0142 (4)0.0001 (3)0.0044 (3)0.0000 (3)
C160.0232 (5)0.0271 (5)0.0218 (6)0.0002 (4)0.0115 (4)0.0014 (5)
Geometric parameters (Å, º) top
Br1—C141.9017 (12)C8—H8A0.9300
O1—C71.2286 (16)C9—C101.4664 (17)
O2—C31.3632 (14)C9—H9A0.9300
O2—C161.4312 (18)C10—C111.4000 (16)
C1—C21.3861 (16)C10—C151.4042 (17)
C1—C61.4048 (16)C11—C121.3898 (19)
C1—H1A0.9300C11—H11A0.9300
C2—C31.3961 (18)C12—C131.3865 (19)
C2—H2A0.9300C12—H12A0.9300
C3—C41.3957 (17)C13—C141.3941 (17)
C4—C51.3910 (16)C13—H13A0.9300
C4—H4A0.9300C14—C151.3818 (17)
C5—C61.3960 (17)C15—H15A0.9300
C5—H5A0.9300C16—H16A0.9600
C6—C71.4857 (16)C16—H16B0.9600
C7—C81.4833 (18)C16—H16C0.9600
C8—C91.3391 (16)
C3—O2—C16117.54 (10)C8—C9—H9A116.8
C2—C1—C6120.37 (11)C10—C9—H9A116.8
C2—C1—H1A119.8C11—C10—C15119.07 (11)
C6—C1—H1A119.8C11—C10—C9118.68 (11)
C1—C2—C3120.13 (11)C15—C10—C9122.23 (10)
C1—C2—H2A119.9C12—C11—C10120.72 (12)
C3—C2—H2A119.9C12—C11—H11A119.6
O2—C3—C4124.17 (11)C10—C11—H11A119.6
O2—C3—C2115.41 (10)C13—C12—C11120.50 (11)
C4—C3—C2120.42 (11)C13—C12—H12A119.8
C5—C4—C3118.80 (11)C11—C12—H12A119.8
C5—C4—H4A120.6C12—C13—C14118.38 (11)
C3—C4—H4A120.6C12—C13—H13A120.8
C4—C5—C6121.70 (11)C14—C13—H13A120.8
C4—C5—H5A119.2C15—C14—C13122.33 (11)
C6—C5—H5A119.2C15—C14—Br1118.76 (9)
C5—C6—C1118.55 (10)C13—C14—Br1118.89 (9)
C5—C6—C7118.98 (10)C14—C15—C10119.01 (10)
C1—C6—C7122.38 (11)C14—C15—H15A120.5
O1—C7—C8121.02 (11)C10—C15—H15A120.5
O1—C7—C6120.84 (11)O2—C16—H16A109.5
C8—C7—C6118.14 (11)O2—C16—H16B109.5
C9—C8—C7121.48 (11)H16A—C16—H16B109.5
C9—C8—H8A119.3O2—C16—H16C109.5
C7—C8—H8A119.3H16A—C16—H16C109.5
C8—C9—C10126.44 (11)H16B—C16—H16C109.5
C6—C1—C2—C30.15 (19)O1—C7—C8—C919.6 (2)
C16—O2—C3—C40.81 (18)C6—C7—C8—C9159.93 (12)
C16—O2—C3—C2179.74 (12)C7—C8—C9—C10177.52 (12)
C1—C2—C3—O2178.05 (11)C8—C9—C10—C11173.94 (13)
C1—C2—C3—C41.43 (19)C8—C9—C10—C157.93 (19)
O2—C3—C4—C5177.76 (12)C15—C10—C11—C120.51 (18)
C2—C3—C4—C51.67 (18)C9—C10—C11—C12177.68 (11)
C3—C4—C5—C60.35 (19)C10—C11—C12—C130.39 (19)
C4—C5—C6—C11.18 (19)C11—C12—C13—C140.14 (19)
C4—C5—C6—C7175.49 (12)C12—C13—C14—C150.02 (18)
C2—C1—C6—C51.43 (18)C12—C13—C14—Br1178.23 (9)
C2—C1—C6—C7175.13 (12)C13—C14—C15—C100.15 (17)
C5—C6—C7—O113.2 (2)Br1—C14—C15—C10178.11 (9)
C1—C6—C7—O1163.35 (14)C11—C10—C15—C140.38 (17)
C5—C6—C7—C8167.25 (12)C9—C10—C15—C14177.74 (11)
C1—C6—C7—C816.21 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···O2i0.932.513.4060 (16)163
C16—H16A···O1ii0.962.573.5028 (18)165
Symmetry codes: (i) x1, y1, z; (ii) x+1, y, z.
 

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