Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704946X/gw2025sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704946X/gw2025Isup2.hkl |
CCDC reference: 667350
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- R factor = 0.067
- wR factor = 0.275
- Data-to-parameter ratio = 25.5
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR) is > 1.50 Tmin and Tmax reported: 0.550 1.000 Tmin and Tmax expected: 0.042 0.138 RR = 1.791 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 35 Perc. PLAT060_ALERT_3_B Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.76
Alert level C RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.275 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.14 PLAT084_ALERT_2_C High R2 Value .................................. 0.27 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.95 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.69 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C5 - C6 .. 5.31 su PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
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 0.138 Tmax scaled 0.138 Tmin scaled 0.076
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 7 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 7 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures see: Butcher et al. (2006a,b); Harrison et al. (2006). For related literature see: Fichou et al. (1988); Tam et al. (1989); Goto et al. (1991); Cho et al. (1996); Uchida et al. (1998); Holla et al. (2001, 2006); Indira et al. (2002); Zhao et al. (2002); Sarojini et al. (2006); Shivarama Holla et al. (2001).
2,3-Dibromo-3-[3,5-dibromo-4-(ethylamino)phenyl]-1- (2,4-dichlorophenyl)propan-1-one (6.37 g, 0.01 mol) is mixed with triethylamine (5 ml, 0.05 mol) in toluene (80 ml) (Fig. 3). This mixture was stirred well for 24 hrs. and the precipitated triethyamine hydrobromide was filtered. [Triethylene hydrobromide is produced during the dehydrobrominaton of the corresponding 2,3 dibromopropanone. The HBr produced forms a salt with triethyl amine which is added to dehydrobominate the chalcone dibromide and the reaction produces 2-bromopropenone (Shivarama Holla et al., 2001)]. The solvent was then removed under reduced pressure. The resulting solid mass obtained on cooling was collected by filtration. The compound was dried and recrystallized from a 1: 1 mixture of acetone: toluene (m.p.: 393–395 K). Analysis found: C 36.58, H 2.14, N 2.47%; C17H12Br3Cl2NO requires: C 36.66, H 2.17, N 2.52%.
H1 was refined isotropically [N1—H1 = 0.89 (1) Å] and all other H atoms were then refined using a riding model with and C—H = 0.93–0.97 Å, and with Uiso(H) = 1.19–1.49Ueq(C,N). The maximum residual electron density peaks of 0.91 and -1.22 e Å3, were located at 0.08 and 0.65 Å from Br3 and Br2, respectively.
The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crystals, alkali halide crystals and non-linear optical (NLO) crystals. The NLO effect in the organic molecules originates from a strong donor-acceptor intermolecular interaction, delocalized π-electron system, and also due to the ability to crystallize in a non-centrosymmetric space group. Among several organic compounds reported for NLO property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show NLO property with two planar rings connected through a conjugated double bond (Goto et al. 1991; Uchida et al. 1998; Tam et al. 1989; Indira et al. 2002, Sarojini et al. 2006). Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of an acentric crystal (Fichou et al. 1988). The molecular hyperpolarizability β are strongly influenced not only by the electronic effect but also by the steric effect of the substituent (Cho et al. 1996). A bromo group, therefore, can obviously improve the molecular first order hyperpolarizabilities and can effectively reduce the dipole-dipole interactions between the molecules (Zhao et al. 2002). Alpha-bromochalcones are used to synthesize triazolothiadiazines which showed promising antiproliferative activity (Holla et al. 2001, 2006). The structures of a few alpha-bromochalcones viz., 2-bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl] prop-2-en-1-one (Butcher et al. 2006a); 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl] propan-1-one (Butcher et al. 2006b) and 2-Bromo-1-chlorophenyl-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al. 2006) have been published. Prompted by this and in continuation of our quest to synthesize newer materials which can find use in Photonics industries, we have synthesized a new a-bromochalcone, (I), C17H12Br3Cl2NO and its crystal structure is reported here.
The mean planes of the 3,5-dibromo-4-phenyl and 2,4-dichlorophenyl groups are separated by a dihedral angle of 72.4 (2)° (Fig. 1). The dihedral angles between the 2-bromo-prop-2-en-1-one group and the two phenyl ring groups (3,5-dibromo-4-phenyl and 2,4-dichlorophenyl) are 71.1 (1) and 10.9 (4)°, respectively.
Crystal packing is stabilized by intermolecular N1—H1···O1 hydrogen bond interactions between the ethyl amino hydrogen atom (H1) and the propyl ketone oxygen atom (O1) with the 3,5-dibromo-4-phenyl rings linked in chains in an alternate inverted pattern parallel and oblique to the ac face and diagonal along the a axis of the unit cell (Fig. 2). Intramolecular hydrogen bonds between the ethyl amino hydrogen atom and the 5-bromo atom from the 3,5-dibromo-4-phenyl group [N1—H1···Br3 (H1···Br3 = 2.63 (0))] Å] provide additonal strength to the molecule within the asymmetric unit.
For related structures see: Butcher et al. (2006a,b); Harrison et al. (2006). For related literature see: Fichou et al. (1988); Tam et al. (1989); Goto et al. (1991); Cho et al. (1996); Uchida et al. (1998); Holla et al. (2001, 2006); Indira et al. (2002); Zhao et al. (2002); Sarojini et al. (2006); Shivarama Holla et al. (2001).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); 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 (Bruker, 2000).
C17H12Br3Cl2NO | F(000) = 1072 |
Mr = 556.91 | Dx = 1.997 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4393 reflections |
a = 9.7939 (4) Å | θ = 4.7–32.4° |
b = 9.7333 (4) Å | µ = 6.83 mm−1 |
c = 19.4436 (6) Å | T = 296 K |
β = 91.635 (3)° | Chunk, pale yellow |
V = 1852.74 (12) Å3 | 0.51 × 0.43 × 0.29 mm |
Z = 4 |
Oxford Diffraction Gemini R CCD diffractometer | 5670 independent reflections |
Radiation source: fine-focus sealed tube | 1957 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.7° |
φ and ω scans | h = −13→14 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −10→14 |
Tmin = 0.550, Tmax = 1.000 | l = −28→27 |
18303 measured reflections |
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)] = 0.067 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.275 | w = 1/[σ2(Fo2) + (0.1284P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
5670 reflections | Δρmax = 0.91 e Å−3 |
222 parameters | Δρmin = −1.22 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0063 (12) |
C17H12Br3Cl2NO | V = 1852.74 (12) Å3 |
Mr = 556.91 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.7939 (4) Å | µ = 6.83 mm−1 |
b = 9.7333 (4) Å | T = 296 K |
c = 19.4436 (6) Å | 0.51 × 0.43 × 0.29 mm |
β = 91.635 (3)° |
Oxford Diffraction Gemini R CCD diffractometer | 5670 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 1957 reflections with I > 2σ(I) |
Tmin = 0.550, Tmax = 1.000 | Rint = 0.052 |
18303 measured reflections |
R[F2 > 2σ(F2)] = 0.067 | 0 restraints |
wR(F2) = 0.275 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.91 e Å−3 |
5670 reflections | Δρmin = −1.22 e Å−3 |
222 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 1.08392 (12) | 0.40693 (12) | −0.08410 (5) | 0.0801 (4) | |
Br2 | 0.61985 (14) | −0.18958 (12) | −0.00324 (6) | 0.0859 (5) | |
Br3 | 0.91770 (10) | 0.21197 (11) | 0.15167 (4) | 0.0642 (4) | |
Cl1 | 0.8346 (3) | −0.0762 (3) | −0.44044 (14) | 0.0842 (8) | |
Cl2 | 0.7686 (2) | 0.3262 (3) | −0.25570 (12) | 0.0642 (6) | |
O1 | 1.1575 (7) | 0.3537 (7) | −0.2283 (3) | 0.0708 (19) | |
N1 | 0.6938 (7) | −0.0046 (9) | 0.1267 (4) | 0.062 (2) | |
H1 | 0.704 (10) | 0.051 (10) | 0.163 (5) | 0.075* | |
C1 | 1.0030 (8) | 0.1851 (8) | −0.2672 (4) | 0.0458 (19) | |
C2 | 1.0855 (8) | 0.0894 (10) | −0.2993 (4) | 0.053 (2) | |
H2A | 1.1759 | 0.0792 | −0.2842 | 0.064* | |
C3 | 1.0360 (9) | 0.0096 (10) | −0.3528 (5) | 0.062 (2) | |
H3A | 1.0923 | −0.0533 | −0.3741 | 0.075* | |
C4 | 0.9006 (11) | 0.0247 (10) | −0.3744 (5) | 0.064 (2) | |
C5 | 0.8164 (9) | 0.1187 (9) | −0.3441 (4) | 0.055 (2) | |
H5A | 0.7260 | 0.1287 | −0.3592 | 0.066* | |
C6 | 0.8700 (9) | 0.1993 (9) | −0.2898 (4) | 0.053 (2) | |
C7 | 1.0664 (8) | 0.2737 (9) | −0.2120 (4) | 0.054 (2) | |
C8 | 1.0235 (8) | 0.2615 (9) | −0.1405 (4) | 0.050 (2) | |
C9 | 0.9444 (8) | 0.1596 (8) | −0.1201 (4) | 0.0458 (18) | |
H9A | 0.9182 | 0.1008 | −0.1558 | 0.055* | |
C10 | 0.8895 (7) | 0.1190 (8) | −0.0547 (3) | 0.0434 (18) | |
C11 | 0.7920 (8) | 0.0112 (7) | −0.0549 (4) | 0.0407 (16) | |
H11A | 0.7680 | −0.0309 | −0.0965 | 0.049* | |
C12 | 0.7322 (7) | −0.0329 (9) | 0.0036 (4) | 0.0477 (19) | |
C13 | 0.7570 (8) | 0.0320 (8) | 0.0678 (4) | 0.0440 (18) | |
C14 | 0.8579 (8) | 0.1315 (8) | 0.0674 (3) | 0.0429 (17) | |
C15 | 0.9201 (8) | 0.1790 (8) | 0.0082 (4) | 0.0439 (18) | |
H15A | 0.9823 | 0.2511 | 0.0112 | 0.053* | |
C16 | 0.5512 (11) | −0.0216 (13) | 0.1337 (5) | 0.083 (3) | |
H16A | 0.5113 | −0.0515 | 0.0900 | 0.099* | |
H16B | 0.5111 | 0.0665 | 0.1448 | 0.099* | |
C17 | 0.5162 (16) | −0.1207 (15) | 0.1867 (8) | 0.121 (5) | |
H17A | 0.4215 | −0.1451 | 0.1814 | 0.181* | |
H17B | 0.5326 | −0.0808 | 0.2313 | 0.181* | |
H17C | 0.5714 | −0.2015 | 0.1822 | 0.181* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.1079 (9) | 0.0730 (8) | 0.0607 (6) | −0.0378 (6) | 0.0233 (5) | −0.0105 (5) |
Br2 | 0.1158 (10) | 0.0712 (8) | 0.0718 (7) | −0.0343 (6) | 0.0229 (6) | −0.0091 (5) |
Br3 | 0.0769 (7) | 0.0760 (7) | 0.0400 (5) | −0.0135 (5) | 0.0057 (4) | −0.0073 (4) |
Cl1 | 0.094 (2) | 0.0786 (18) | 0.0798 (18) | −0.0087 (15) | −0.0026 (14) | −0.0277 (14) |
Cl2 | 0.0594 (14) | 0.0731 (16) | 0.0606 (13) | 0.0116 (11) | 0.0109 (10) | −0.0024 (11) |
O1 | 0.090 (5) | 0.073 (4) | 0.050 (3) | −0.034 (4) | 0.019 (3) | −0.006 (3) |
N1 | 0.047 (4) | 0.096 (7) | 0.044 (4) | −0.017 (4) | 0.009 (3) | 0.010 (4) |
C1 | 0.055 (5) | 0.042 (5) | 0.040 (4) | −0.001 (4) | 0.000 (3) | 0.020 (3) |
C2 | 0.038 (4) | 0.062 (6) | 0.061 (5) | 0.017 (4) | 0.017 (3) | 0.013 (4) |
C3 | 0.044 (5) | 0.060 (6) | 0.084 (6) | 0.009 (4) | 0.027 (4) | 0.009 (5) |
C4 | 0.080 (7) | 0.063 (6) | 0.050 (5) | −0.017 (5) | 0.017 (4) | 0.005 (4) |
C5 | 0.057 (5) | 0.059 (5) | 0.047 (5) | −0.020 (4) | −0.011 (4) | 0.002 (4) |
C6 | 0.059 (5) | 0.052 (5) | 0.049 (4) | 0.010 (4) | 0.015 (4) | 0.016 (4) |
C7 | 0.045 (5) | 0.062 (6) | 0.054 (5) | −0.009 (4) | 0.003 (4) | 0.009 (4) |
C8 | 0.042 (4) | 0.064 (6) | 0.043 (4) | 0.012 (4) | 0.002 (3) | 0.012 (4) |
C9 | 0.053 (5) | 0.045 (4) | 0.041 (4) | 0.001 (4) | 0.011 (3) | 0.013 (3) |
C10 | 0.037 (4) | 0.059 (5) | 0.034 (3) | 0.002 (3) | −0.001 (3) | 0.019 (3) |
C11 | 0.040 (4) | 0.035 (4) | 0.047 (4) | 0.006 (3) | 0.000 (3) | −0.006 (3) |
C12 | 0.029 (4) | 0.063 (5) | 0.051 (4) | −0.018 (3) | 0.006 (3) | −0.001 (4) |
C13 | 0.049 (4) | 0.045 (4) | 0.038 (4) | 0.006 (4) | 0.006 (3) | 0.003 (3) |
C14 | 0.052 (5) | 0.045 (4) | 0.033 (3) | −0.005 (4) | 0.018 (3) | 0.005 (3) |
C15 | 0.051 (4) | 0.044 (5) | 0.037 (4) | −0.005 (4) | −0.005 (3) | 0.005 (3) |
C16 | 0.073 (8) | 0.105 (9) | 0.071 (7) | 0.012 (6) | −0.001 (5) | −0.005 (6) |
C17 | 0.140 (13) | 0.093 (10) | 0.131 (11) | −0.042 (9) | 0.048 (9) | 0.023 (9) |
Br1—C8 | 1.877 (9) | C7—C8 | 1.468 (11) |
Br2—C12 | 1.882 (8) | C8—C9 | 1.327 (11) |
Br3—C14 | 1.894 (7) | C9—C10 | 1.449 (9) |
Cl1—C4 | 1.728 (10) | C9—H9A | 0.9300 |
Cl2—C6 | 1.729 (9) | C10—C15 | 1.380 (10) |
O1—C7 | 1.232 (10) | C10—C11 | 1.419 (11) |
N1—C13 | 1.366 (10) | C11—C12 | 1.364 (11) |
N1—C16 | 1.418 (13) | C11—H11A | 0.9300 |
N1—H1 | 0.89 (10) | C12—C13 | 1.414 (10) |
C1—C6 | 1.369 (11) | C13—C14 | 1.383 (11) |
C1—C2 | 1.393 (11) | C14—C15 | 1.396 (10) |
C1—C7 | 1.497 (12) | C15—H15A | 0.9300 |
C2—C3 | 1.375 (13) | C16—C17 | 1.459 (16) |
C2—H2A | 0.9300 | C16—H16A | 0.9700 |
C3—C4 | 1.388 (13) | C16—H16B | 0.9700 |
C3—H3A | 0.9300 | C17—H17A | 0.9600 |
C4—C5 | 1.375 (14) | C17—H17B | 0.9600 |
C5—C6 | 1.405 (12) | C17—H17C | 0.9600 |
C5—H5A | 0.9300 | ||
C13—N1—C16 | 125.6 (8) | C15—C10—C11 | 116.4 (6) |
C13—N1—H1 | 118 (7) | C15—C10—C9 | 125.9 (7) |
C16—N1—H1 | 95 (7) | C11—C10—C9 | 117.7 (7) |
C6—C1—C2 | 118.8 (8) | C12—C11—C10 | 122.4 (7) |
C6—C1—C7 | 122.9 (8) | C12—C11—H11A | 118.8 |
C2—C1—C7 | 118.2 (7) | C10—C11—H11A | 118.8 |
C3—C2—C1 | 121.4 (8) | C11—C12—C13 | 121.9 (7) |
C3—C2—H2A | 119.3 | C11—C12—Br2 | 117.4 (6) |
C1—C2—H2A | 119.3 | C13—C12—Br2 | 120.7 (6) |
C2—C3—C4 | 118.8 (8) | N1—C13—C14 | 121.9 (7) |
C2—C3—H3A | 120.6 | N1—C13—C12 | 123.6 (8) |
C4—C3—H3A | 120.6 | C14—C13—C12 | 114.4 (7) |
C5—C4—C3 | 121.4 (9) | C13—C14—C15 | 124.4 (7) |
C5—C4—Cl1 | 118.7 (8) | C13—C14—Br3 | 119.2 (5) |
C3—C4—Cl1 | 119.9 (8) | C15—C14—Br3 | 116.4 (6) |
C4—C5—C6 | 118.5 (8) | C10—C15—C14 | 120.1 (7) |
C4—C5—H5A | 120.8 | C10—C15—H15A | 120.0 |
C6—C5—H5A | 120.8 | C14—C15—H15A | 120.0 |
C1—C6—C5 | 121.2 (8) | N1—C16—C17 | 113.4 (10) |
C1—C6—Cl2 | 120.0 (7) | N1—C16—H16A | 108.9 |
C5—C6—Cl2 | 118.7 (7) | C17—C16—H16A | 108.9 |
O1—C7—C8 | 121.6 (8) | N1—C16—H16B | 108.9 |
O1—C7—C1 | 117.9 (8) | C17—C16—H16B | 108.9 |
C8—C7—C1 | 120.5 (7) | H16A—C16—H16B | 107.7 |
C9—C8—C7 | 122.0 (8) | C16—C17—H17A | 109.5 |
C9—C8—Br1 | 124.5 (6) | C16—C17—H17B | 109.5 |
C7—C8—Br1 | 113.4 (6) | H17A—C17—H17B | 109.5 |
C8—C9—C10 | 134.5 (8) | C16—C17—H17C | 109.5 |
C8—C9—H9A | 112.8 | H17A—C17—H17C | 109.5 |
C10—C9—H9A | 112.8 | H17B—C17—H17C | 109.5 |
C6—C1—C2—C3 | 0.0 (12) | Br1—C8—C9—C10 | −5.1 (14) |
C7—C1—C2—C3 | −176.5 (7) | C8—C9—C10—C15 | −5.9 (14) |
C1—C2—C3—C4 | −0.7 (13) | C8—C9—C10—C11 | 171.8 (9) |
C2—C3—C4—C5 | 1.0 (13) | C15—C10—C11—C12 | −0.7 (11) |
C2—C3—C4—Cl1 | −178.8 (7) | C9—C10—C11—C12 | −178.7 (7) |
C3—C4—C5—C6 | −0.6 (13) | C10—C11—C12—C13 | 4.1 (12) |
Cl1—C4—C5—C6 | 179.2 (6) | C10—C11—C12—Br2 | −173.3 (6) |
C2—C1—C6—C5 | 0.4 (11) | C16—N1—C13—C14 | 134.1 (10) |
C7—C1—C6—C5 | 176.7 (7) | C16—N1—C13—C12 | −50.0 (14) |
C2—C1—C6—Cl2 | −175.0 (6) | C11—C12—C13—N1 | 176.5 (8) |
C7—C1—C6—Cl2 | 1.4 (10) | Br2—C12—C13—N1 | −6.1 (11) |
C4—C5—C6—C1 | −0.1 (12) | C11—C12—C13—C14 | −7.3 (11) |
C4—C5—C6—Cl2 | 175.4 (6) | Br2—C12—C13—C14 | 170.1 (6) |
C6—C1—C7—O1 | −112.8 (10) | N1—C13—C14—C15 | −176.0 (8) |
C2—C1—C7—O1 | 63.6 (11) | C12—C13—C14—C15 | 7.8 (12) |
C6—C1—C7—C8 | 69.0 (11) | N1—C13—C14—Br3 | 3.7 (11) |
C2—C1—C7—C8 | −114.6 (9) | C12—C13—C14—Br3 | −172.6 (6) |
O1—C7—C8—C9 | −167.5 (9) | C11—C10—C15—C14 | 1.0 (11) |
C1—C7—C8—C9 | 10.6 (12) | C9—C10—C15—C14 | 178.8 (7) |
O1—C7—C8—Br1 | 15.4 (11) | C13—C14—C15—C10 | −4.9 (12) |
C1—C7—C8—Br1 | −166.6 (6) | Br3—C14—C15—C10 | 175.4 (6) |
C7—C8—C9—C10 | 178.1 (8) | C13—N1—C16—C17 | 151.4 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.89 (10) | 2.37 (10) | 3.207 (10) | 158 (9) |
N1—H1···Br3 | 0.89 (10) | 2.63 (10) | 3.070 (8) | 112 (8) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C17H12Br3Cl2NO |
Mr | 556.91 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 9.7939 (4), 9.7333 (4), 19.4436 (6) |
β (°) | 91.635 (3) |
V (Å3) | 1852.74 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 6.83 |
Crystal size (mm) | 0.51 × 0.43 × 0.29 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.550, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18303, 5670, 1957 |
Rint | 0.052 |
(sin θ/λ)max (Å−1) | 0.755 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.067, 0.275, 1.04 |
No. of reflections | 5670 |
No. of parameters | 222 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.91, −1.22 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.89 (10) | 2.37 (10) | 3.207 (10) | 158 (9) |
N1—H1···Br3 | 0.89 (10) | 2.63 (10) | 3.070 (8) | 112 (8) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
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The important goal of crystal growth is the improvement of microscopic and macroscopic homogeneity, which is a necessity for any application. Different types of crystals being used are semiconductor crystals, oxide crystals, alkali halide crystals and non-linear optical (NLO) crystals. The NLO effect in the organic molecules originates from a strong donor-acceptor intermolecular interaction, delocalized π-electron system, and also due to the ability to crystallize in a non-centrosymmetric space group. Among several organic compounds reported for NLO property, chalcone derivatives are noticeable materials for their excellent blue light transmittance and good crystallizability. They provide a necessary configuration to show NLO property with two planar rings connected through a conjugated double bond (Goto et al. 1991; Uchida et al. 1998; Tam et al. 1989; Indira et al. 2002, Sarojini et al. 2006). Substitution on either of the phenyl rings greatly influences non-centrosymmetric crystal packing. It is speculated that in order to improve the activity, more bulky substituents should be introduced to increase the spontaneous polarization of an acentric crystal (Fichou et al. 1988). The molecular hyperpolarizability β are strongly influenced not only by the electronic effect but also by the steric effect of the substituent (Cho et al. 1996). A bromo group, therefore, can obviously improve the molecular first order hyperpolarizabilities and can effectively reduce the dipole-dipole interactions between the molecules (Zhao et al. 2002). Alpha-bromochalcones are used to synthesize triazolothiadiazines which showed promising antiproliferative activity (Holla et al. 2001, 2006). The structures of a few alpha-bromochalcones viz., 2-bromo-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl] prop-2-en-1-one (Butcher et al. 2006a); 2-bromo-3-hydroxy-1-(4-methylphenyl)-3-[4-(methylsulfanyl)phenyl] propan-1-one (Butcher et al. 2006b) and 2-Bromo-1-chlorophenyl-3-(4-methoxyphenyl)prop-2-en-1-one (Harrison et al. 2006) have been published. Prompted by this and in continuation of our quest to synthesize newer materials which can find use in Photonics industries, we have synthesized a new a-bromochalcone, (I), C17H12Br3Cl2NO and its crystal structure is reported here.
The mean planes of the 3,5-dibromo-4-phenyl and 2,4-dichlorophenyl groups are separated by a dihedral angle of 72.4 (2)° (Fig. 1). The dihedral angles between the 2-bromo-prop-2-en-1-one group and the two phenyl ring groups (3,5-dibromo-4-phenyl and 2,4-dichlorophenyl) are 71.1 (1) and 10.9 (4)°, respectively.
Crystal packing is stabilized by intermolecular N1—H1···O1 hydrogen bond interactions between the ethyl amino hydrogen atom (H1) and the propyl ketone oxygen atom (O1) with the 3,5-dibromo-4-phenyl rings linked in chains in an alternate inverted pattern parallel and oblique to the ac face and diagonal along the a axis of the unit cell (Fig. 2). Intramolecular hydrogen bonds between the ethyl amino hydrogen atom and the 5-bromo atom from the 3,5-dibromo-4-phenyl group [N1—H1···Br3 (H1···Br3 = 2.63 (0))] Å] provide additonal strength to the molecule within the asymmetric unit.