In the title compound, C
16H
13BrO
2, 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
CCDC reference: 627666
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (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
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
C16H13BrO2 | F(000) = 320 |
Mr = 317.17 | Dx = 1.610 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 7113 reflections |
a = 10.2917 (1) Å | θ = 2.7–37.5° |
b = 3.8970 (1) Å | µ = 3.14 mm−1 |
c = 17.0919 (2) Å | T = 100 K |
β = 107.313 (1)° | Block, yellow |
V = 654.46 (1) Å3 | 0.40 × 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 tube | 6194 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.5°, θmin = 1.3° |
ω scans | h = −17→17 |
Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −6→6 |
Tmin = 0.369, Tmax = 0.391 | l = −29→28 |
31059 measured reflections | |
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)] = 0.024 | H-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 reflections | Δρmax = 0.64 e Å−3 |
173 parameters | Δρmin = −0.37 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2981 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Br1 | 0.357551 (11) | 0.79782 (5) | 0.574543 (6) | 0.02143 (3) | |
O1 | 0.28008 (10) | 0.9906 (3) | 0.10248 (7) | 0.0264 (2) | |
O2 | 0.91154 (9) | 1.0452 (3) | 0.14142 (6) | 0.02069 (17) | |
C1 | 0.63215 (12) | 0.8777 (3) | 0.22358 (8) | 0.0174 (2) | |
H1A | 0.6200 | 0.7819 | 0.2707 | 0.021* | |
C2 | 0.76174 (12) | 0.9006 (3) | 0.21518 (8) | 0.0187 (2) | |
H2A | 0.8362 | 0.8197 | 0.2566 | 0.022* | |
C3 | 0.78077 (11) | 1.0448 (3) | 0.14462 (8) | 0.01631 (18) | |
C4 | 0.67021 (12) | 1.1740 (3) | 0.08284 (8) | 0.01701 (18) | |
H4A | 0.6829 | 1.2756 | 0.0364 | 0.020* | |
C5 | 0.54069 (11) | 1.1481 (3) | 0.09195 (7) | 0.01675 (19) | |
H5A | 0.4666 | 1.2326 | 0.0508 | 0.020* | |
C6 | 0.51905 (11) | 0.9985 (3) | 0.16124 (7) | 0.01585 (18) | |
C7 | 0.37727 (12) | 0.9554 (3) | 0.16440 (8) | 0.0184 (2) | |
C8 | 0.35654 (12) | 0.8662 (3) | 0.24421 (8) | 0.0190 (2) | |
H8A | 0.4259 | 0.9089 | 0.2923 | 0.023* | |
C9 | 0.24013 (12) | 0.7255 (3) | 0.24851 (8) | 0.0180 (2) | |
H9A | 0.1745 | 0.6783 | 0.1990 | 0.022* | |
C10 | 0.20588 (11) | 0.6387 (3) | 0.32349 (8) | 0.01608 (18) | |
C11 | 0.08441 (11) | 0.4626 (3) | 0.31654 (8) | 0.01783 (19) | |
H11A | 0.0293 | 0.3963 | 0.2651 | 0.021* | |
C12 | 0.04532 (12) | 0.3856 (3) | 0.38569 (9) | 0.0199 (2) | |
H12A | −0.0359 | 0.2697 | 0.3801 | 0.024* | |
C13 | 0.12654 (12) | 0.4804 (3) | 0.46296 (8) | 0.0186 (2) | |
H13A | 0.1009 | 0.4290 | 0.5094 | 0.022* | |
C14 | 0.24757 (11) | 0.6546 (3) | 0.46931 (7) | 0.01674 (19) | |
C15 | 0.28875 (11) | 0.7349 (3) | 0.40159 (7) | 0.0165 (2) | |
H15A | 0.3701 | 0.8508 | 0.4076 | 0.020* | |
C16 | 0.93644 (13) | 1.1917 (4) | 0.07045 (9) | 0.0230 (2) | |
H16A | 1.0320 | 1.1802 | 0.0760 | 0.034* | |
H16B | 0.9075 | 1.4270 | 0.0651 | 0.034* | |
H16C | 0.8865 | 1.0662 | 0.0226 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02897 (5) | 0.01920 (5) | 0.01360 (5) | 0.00116 (6) | 0.00248 (3) | −0.00054 (5) |
O1 | 0.0187 (4) | 0.0426 (6) | 0.0166 (4) | −0.0007 (4) | 0.0033 (3) | 0.0031 (4) |
O2 | 0.0161 (3) | 0.0288 (5) | 0.0178 (4) | 0.0003 (3) | 0.0060 (3) | 0.0010 (3) |
C1 | 0.0185 (4) | 0.0204 (5) | 0.0129 (4) | 0.0011 (3) | 0.0042 (3) | 0.0010 (3) |
C2 | 0.0182 (4) | 0.0221 (5) | 0.0146 (5) | 0.0018 (4) | 0.0033 (3) | 0.0012 (4) |
C3 | 0.0172 (4) | 0.0177 (4) | 0.0142 (5) | −0.0004 (3) | 0.0049 (3) | −0.0018 (4) |
C4 | 0.0189 (4) | 0.0184 (4) | 0.0136 (5) | −0.0011 (4) | 0.0046 (3) | 0.0003 (4) |
C5 | 0.0175 (4) | 0.0185 (5) | 0.0131 (5) | −0.0005 (4) | 0.0028 (3) | 0.0006 (4) |
C6 | 0.0168 (4) | 0.0179 (4) | 0.0127 (5) | −0.0004 (3) | 0.0042 (3) | −0.0008 (4) |
C7 | 0.0174 (4) | 0.0227 (5) | 0.0154 (5) | −0.0007 (4) | 0.0055 (4) | −0.0001 (4) |
C8 | 0.0197 (4) | 0.0241 (6) | 0.0138 (5) | −0.0032 (4) | 0.0057 (3) | −0.0011 (4) |
C9 | 0.0185 (4) | 0.0216 (6) | 0.0143 (5) | −0.0009 (3) | 0.0055 (3) | 0.0000 (3) |
C10 | 0.0154 (4) | 0.0179 (5) | 0.0150 (5) | 0.0003 (3) | 0.0045 (3) | 0.0002 (4) |
C11 | 0.0161 (4) | 0.0191 (5) | 0.0176 (5) | −0.0004 (4) | 0.0039 (4) | 0.0001 (4) |
C12 | 0.0180 (4) | 0.0212 (5) | 0.0214 (6) | −0.0010 (3) | 0.0070 (4) | 0.0016 (4) |
C13 | 0.0203 (4) | 0.0188 (5) | 0.0189 (5) | 0.0019 (4) | 0.0089 (4) | 0.0027 (4) |
C14 | 0.0193 (4) | 0.0158 (5) | 0.0146 (5) | 0.0023 (4) | 0.0042 (3) | 0.0004 (4) |
C15 | 0.0167 (4) | 0.0183 (6) | 0.0142 (4) | −0.0001 (3) | 0.0044 (3) | 0.0000 (3) |
C16 | 0.0232 (5) | 0.0271 (5) | 0.0218 (6) | −0.0002 (4) | 0.0115 (4) | 0.0014 (5) |
Geometric parameters (Å, º) top
Br1—C14 | 1.9017 (12) | C8—H8A | 0.9300 |
O1—C7 | 1.2286 (16) | C9—C10 | 1.4664 (17) |
O2—C3 | 1.3632 (14) | C9—H9A | 0.9300 |
O2—C16 | 1.4312 (18) | C10—C11 | 1.4000 (16) |
C1—C2 | 1.3861 (16) | C10—C15 | 1.4042 (17) |
C1—C6 | 1.4048 (16) | C11—C12 | 1.3898 (19) |
C1—H1A | 0.9300 | C11—H11A | 0.9300 |
C2—C3 | 1.3961 (18) | C12—C13 | 1.3865 (19) |
C2—H2A | 0.9300 | C12—H12A | 0.9300 |
C3—C4 | 1.3957 (17) | C13—C14 | 1.3941 (17) |
C4—C5 | 1.3910 (16) | C13—H13A | 0.9300 |
C4—H4A | 0.9300 | C14—C15 | 1.3818 (17) |
C5—C6 | 1.3960 (17) | C15—H15A | 0.9300 |
C5—H5A | 0.9300 | C16—H16A | 0.9600 |
C6—C7 | 1.4857 (16) | C16—H16B | 0.9600 |
C7—C8 | 1.4833 (18) | C16—H16C | 0.9600 |
C8—C9 | 1.3391 (16) | | |
| | | |
C3—O2—C16 | 117.54 (10) | C8—C9—H9A | 116.8 |
C2—C1—C6 | 120.37 (11) | C10—C9—H9A | 116.8 |
C2—C1—H1A | 119.8 | C11—C10—C15 | 119.07 (11) |
C6—C1—H1A | 119.8 | C11—C10—C9 | 118.68 (11) |
C1—C2—C3 | 120.13 (11) | C15—C10—C9 | 122.23 (10) |
C1—C2—H2A | 119.9 | C12—C11—C10 | 120.72 (12) |
C3—C2—H2A | 119.9 | C12—C11—H11A | 119.6 |
O2—C3—C4 | 124.17 (11) | C10—C11—H11A | 119.6 |
O2—C3—C2 | 115.41 (10) | C13—C12—C11 | 120.50 (11) |
C4—C3—C2 | 120.42 (11) | C13—C12—H12A | 119.8 |
C5—C4—C3 | 118.80 (11) | C11—C12—H12A | 119.8 |
C5—C4—H4A | 120.6 | C12—C13—C14 | 118.38 (11) |
C3—C4—H4A | 120.6 | C12—C13—H13A | 120.8 |
C4—C5—C6 | 121.70 (11) | C14—C13—H13A | 120.8 |
C4—C5—H5A | 119.2 | C15—C14—C13 | 122.33 (11) |
C6—C5—H5A | 119.2 | C15—C14—Br1 | 118.76 (9) |
C5—C6—C1 | 118.55 (10) | C13—C14—Br1 | 118.89 (9) |
C5—C6—C7 | 118.98 (10) | C14—C15—C10 | 119.01 (10) |
C1—C6—C7 | 122.38 (11) | C14—C15—H15A | 120.5 |
O1—C7—C8 | 121.02 (11) | C10—C15—H15A | 120.5 |
O1—C7—C6 | 120.84 (11) | O2—C16—H16A | 109.5 |
C8—C7—C6 | 118.14 (11) | O2—C16—H16B | 109.5 |
C9—C8—C7 | 121.48 (11) | H16A—C16—H16B | 109.5 |
C9—C8—H8A | 119.3 | O2—C16—H16C | 109.5 |
C7—C8—H8A | 119.3 | H16A—C16—H16C | 109.5 |
C8—C9—C10 | 126.44 (11) | H16B—C16—H16C | 109.5 |
| | | |
C6—C1—C2—C3 | 0.15 (19) | O1—C7—C8—C9 | 19.6 (2) |
C16—O2—C3—C4 | 0.81 (18) | C6—C7—C8—C9 | −159.93 (12) |
C16—O2—C3—C2 | −179.74 (12) | C7—C8—C9—C10 | −177.52 (12) |
C1—C2—C3—O2 | −178.05 (11) | C8—C9—C10—C11 | −173.94 (13) |
C1—C2—C3—C4 | 1.43 (19) | C8—C9—C10—C15 | 7.93 (19) |
O2—C3—C4—C5 | 177.76 (12) | C15—C10—C11—C12 | 0.51 (18) |
C2—C3—C4—C5 | −1.67 (18) | C9—C10—C11—C12 | −177.68 (11) |
C3—C4—C5—C6 | 0.35 (19) | C10—C11—C12—C13 | −0.39 (19) |
C4—C5—C6—C1 | 1.18 (19) | C11—C12—C13—C14 | 0.14 (19) |
C4—C5—C6—C7 | −175.49 (12) | C12—C13—C14—C15 | −0.02 (18) |
C2—C1—C6—C5 | −1.43 (18) | C12—C13—C14—Br1 | 178.23 (9) |
C2—C1—C6—C7 | 175.13 (12) | C13—C14—C15—C10 | 0.15 (17) |
C5—C6—C7—O1 | 13.2 (2) | Br1—C14—C15—C10 | −178.11 (9) |
C1—C6—C7—O1 | −163.35 (14) | C11—C10—C15—C14 | −0.38 (17) |
C5—C6—C7—C8 | −167.25 (12) | C9—C10—C15—C14 | 177.74 (11) |
C1—C6—C7—C8 | 16.21 (18) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O2i | 0.93 | 2.51 | 3.4060 (16) | 163 |
C16—H16A···O1ii | 0.96 | 2.57 | 3.5028 (18) | 165 |
Symmetry codes: (i) x−1, y−1, z; (ii) x+1, y, z. |