Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807059089/at2485sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807059089/at2485Isup2.hkl |
CCDC reference: 673015
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.118
- Data-to-parameter ratio = 26.4
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.712 0.877 Tmin(prime) and Tmax expected: 0.806 0.877 RR(prime) = 0.884 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT230_ALERT_2_C Hirshfeld Test Diff for C5A - C6A .. 5.01 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C6A PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 13
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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: Insuasty et al. (2006); Teh et al. (2006); Huang et al. (2006); Qiu et al. (2006a,b); Butcher et al. (2007); Yathirajan et al. (2006, 2007). For related literature, see: Krohnke et al. (1976): Hirsch & Bailey, (1978).
4-Chloroacetophenone (1.54 g, 0.1 mol) in ethanol (30 ml) was mixed with 2-chlorobenzaldehyde (0.7 g, 0.05 mol) and the mixture was treated with an aqueous solution of sodium hydroxide (5 ml, 30%) (Fig. 3). This mixture was stirred well and left for 12 h. The resulting crude solid mass was collected by filtration, washed, dried and recrystallized from toluene (yield 85%., m.p.: 401 K). The initially formed 1-(4-methoxyphenyl)-3-(2-chlorophenyl)prop-2-en-1-one, underwent Michael addition, resulting in the formation of the novel title compound (I). Analysis found: C 63.90, H 3.94%; C23H17Cl3O2 requires: C 63.98, H 3.97%.
The H atoms were placed in their calculated positions and then refined using the riding model with C—H = 0.93 to 0.98 Å, and with Uiso(H) = 1.19 or 1.21Ueq(C).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.
C23H17Cl3O2 | Z = 2 |
Mr = 431.72 | F(000) = 444 |
Triclinic, P1 | Dx = 1.417 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1717 (8) Å | Cell parameters from 4806 reflections |
b = 7.7000 (15) Å | θ = 4.5–32.6° |
c = 18.901 (6) Å | µ = 0.47 mm−1 |
α = 85.88 (2)° | T = 296 K |
β = 83.518 (15)° | Prism, pale yellow |
γ = 77.656 (12)° | 0.45 × 0.39 × 0.28 mm |
V = 1011.9 (4) Å3 |
Oxford Diffraction Gemini R CCD diffractometer | 6690 independent reflections |
Radiation source: fine-focus sealed tube | 3147 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.7°, θmin = 4.6° |
ϕ and ω scans | h = −10→10 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −11→11 |
Tmin = 0.712, Tmax = 0.877 | l = −28→25 |
14729 measured reflections |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.93 | w = 1/[σ2(Fo2) + (0.0598P)2] where P = (Fo2 + 2Fc2)/3 |
6690 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
C23H17Cl3O2 | γ = 77.656 (12)° |
Mr = 431.72 | V = 1011.9 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.1717 (8) Å | Mo Kα radiation |
b = 7.7000 (15) Å | µ = 0.47 mm−1 |
c = 18.901 (6) Å | T = 296 K |
α = 85.88 (2)° | 0.45 × 0.39 × 0.28 mm |
β = 83.518 (15)° |
Oxford Diffraction Gemini R CCD diffractometer | 6690 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 3147 reflections with I > 2σ(I) |
Tmin = 0.712, Tmax = 0.877 | Rint = 0.024 |
14729 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 0.93 | Δρmax = 0.24 e Å−3 |
6690 reflections | Δρmin = −0.33 e Å−3 |
253 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 | ||
Cl | 0.99371 (5) | 0.01789 (6) | 0.20354 (3) | 0.07076 (15) | |
Cl1A | −0.20263 (8) | 0.29570 (8) | 0.60074 (3) | 0.09081 (19) | |
Cl1B | 0.84843 (6) | 0.85651 (6) | 0.01648 (3) | 0.07311 (16) | |
O1A | 0.59359 (15) | 0.16616 (18) | 0.37462 (6) | 0.0739 (4) | |
O1B | 0.22035 (13) | 0.35855 (15) | 0.14247 (6) | 0.0630 (3) | |
C | 0.55268 (17) | 0.10895 (17) | 0.23407 (7) | 0.0392 (3) | |
H0A | 0.6438 | 0.1859 | 0.2371 | 0.047* | |
C1 | 0.65483 (18) | −0.08305 (17) | 0.24669 (7) | 0.0407 (3) | |
C2 | 0.85377 (19) | −0.13735 (19) | 0.23327 (7) | 0.0464 (3) | |
C3 | 0.9461 (2) | −0.3130 (2) | 0.24106 (9) | 0.0629 (4) | |
H3A | 1.0786 | −0.3451 | 0.2314 | 0.075* | |
C4 | 0.8422 (3) | −0.4397 (2) | 0.26302 (10) | 0.0718 (5) | |
H4A | 0.9041 | −0.5583 | 0.2685 | 0.086* | |
C5 | 0.6468 (3) | −0.3926 (2) | 0.27701 (10) | 0.0725 (5) | |
H5A | 0.5758 | −0.4785 | 0.2925 | 0.087* | |
C6 | 0.5560 (2) | −0.2157 (2) | 0.26790 (8) | 0.0572 (4) | |
H6A | 0.4231 | −0.1855 | 0.2765 | 0.069* | |
C1A | 0.37939 (18) | 0.16621 (19) | 0.28840 (7) | 0.0445 (3) | |
H1AA | 0.3097 | 0.2827 | 0.2731 | 0.053* | |
H1AB | 0.2945 | 0.0835 | 0.2886 | 0.053* | |
C2A | 0.4284 (2) | 0.17464 (19) | 0.36322 (7) | 0.0455 (3) | |
C3A | 0.26998 (19) | 0.19997 (18) | 0.42202 (7) | 0.0438 (3) | |
C4A | 0.3106 (2) | 0.2179 (2) | 0.49019 (8) | 0.0632 (4) | |
H4AA | 0.4371 | 0.2101 | 0.4990 | 0.076* | |
C5A | 0.1676 (3) | 0.2470 (3) | 0.54553 (9) | 0.0712 (5) | |
H5AA | 0.1968 | 0.2592 | 0.5914 | 0.085* | |
C6A | −0.0180 (2) | 0.2578 (2) | 0.53224 (8) | 0.0585 (4) | |
C7A | −0.0643 (2) | 0.2376 (2) | 0.46536 (9) | 0.0646 (4) | |
H7AA | −0.1909 | 0.2435 | 0.4571 | 0.078* | |
C8A | 0.0818 (2) | 0.2081 (2) | 0.41048 (8) | 0.0549 (4) | |
H8AA | 0.0525 | 0.1936 | 0.3649 | 0.066* | |
C1B | 0.49133 (18) | 0.12994 (18) | 0.15762 (7) | 0.0421 (3) | |
H1BA | 0.6040 | 0.0926 | 0.1245 | 0.051* | |
H1BB | 0.4045 | 0.0509 | 0.1539 | 0.051* | |
C2B | 0.39471 (18) | 0.31623 (18) | 0.13577 (7) | 0.0423 (3) | |
C3B | 0.51050 (18) | 0.44822 (18) | 0.10689 (7) | 0.0394 (3) | |
C4B | 0.41837 (19) | 0.61665 (19) | 0.08326 (7) | 0.0446 (3) | |
H4BA | 0.2851 | 0.6452 | 0.0864 | 0.054* | |
C5B | 0.5207 (2) | 0.74129 (19) | 0.05538 (8) | 0.0499 (4) | |
H5BA | 0.4577 | 0.8529 | 0.0391 | 0.060* | |
C6B | 0.7180 (2) | 0.69894 (19) | 0.05180 (7) | 0.0462 (3) | |
C7B | 0.81408 (19) | 0.5351 (2) | 0.07542 (8) | 0.0496 (4) | |
H7BA | 0.9473 | 0.5092 | 0.0734 | 0.060* | |
C8B | 0.71080 (19) | 0.40966 (19) | 0.10217 (8) | 0.0473 (3) | |
H8BA | 0.7751 | 0.2975 | 0.1174 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.03547 (19) | 0.0776 (3) | 0.0992 (4) | −0.01499 (18) | −0.0055 (2) | 0.0040 (2) |
Cl1A | 0.0917 (4) | 0.1141 (4) | 0.0619 (3) | −0.0255 (3) | 0.0284 (3) | −0.0169 (3) |
Cl1B | 0.0674 (3) | 0.0560 (3) | 0.0960 (4) | −0.0229 (2) | 0.0084 (2) | 0.0000 (2) |
O1A | 0.0434 (6) | 0.1231 (11) | 0.0596 (7) | −0.0194 (6) | −0.0097 (5) | −0.0207 (7) |
O1B | 0.0355 (5) | 0.0703 (7) | 0.0783 (8) | −0.0073 (5) | −0.0019 (5) | 0.0118 (6) |
C | 0.0321 (6) | 0.0422 (7) | 0.0430 (7) | −0.0085 (5) | −0.0022 (5) | −0.0012 (6) |
C1 | 0.0408 (7) | 0.0434 (7) | 0.0380 (7) | −0.0088 (6) | −0.0050 (6) | −0.0014 (6) |
C2 | 0.0412 (7) | 0.0518 (8) | 0.0449 (8) | −0.0059 (6) | −0.0061 (6) | −0.0035 (6) |
C3 | 0.0597 (9) | 0.0604 (10) | 0.0619 (10) | 0.0079 (8) | −0.0141 (8) | −0.0075 (8) |
C4 | 0.0958 (14) | 0.0450 (9) | 0.0655 (11) | 0.0078 (9) | −0.0128 (10) | −0.0028 (8) |
C5 | 0.0992 (14) | 0.0477 (10) | 0.0722 (12) | −0.0243 (9) | −0.0028 (10) | 0.0048 (8) |
C6 | 0.0560 (9) | 0.0520 (9) | 0.0626 (10) | −0.0152 (7) | 0.0024 (8) | 0.0025 (7) |
C1A | 0.0370 (6) | 0.0525 (8) | 0.0426 (8) | −0.0044 (6) | −0.0054 (6) | −0.0062 (6) |
C2A | 0.0436 (7) | 0.0503 (8) | 0.0434 (8) | −0.0097 (6) | −0.0063 (6) | −0.0047 (6) |
C3A | 0.0489 (8) | 0.0460 (8) | 0.0377 (8) | −0.0106 (6) | −0.0078 (6) | −0.0028 (6) |
C4A | 0.0553 (9) | 0.0898 (12) | 0.0461 (9) | −0.0146 (9) | −0.0080 (8) | −0.0116 (8) |
C5A | 0.0819 (12) | 0.0957 (14) | 0.0375 (9) | −0.0184 (10) | −0.0064 (9) | −0.0131 (8) |
C6A | 0.0639 (10) | 0.0621 (10) | 0.0472 (9) | −0.0140 (8) | 0.0086 (8) | −0.0065 (7) |
C7A | 0.0496 (9) | 0.0892 (13) | 0.0559 (10) | −0.0167 (8) | −0.0001 (8) | −0.0095 (9) |
C8A | 0.0502 (8) | 0.0758 (11) | 0.0395 (8) | −0.0145 (7) | −0.0037 (7) | −0.0059 (7) |
C1B | 0.0411 (7) | 0.0465 (8) | 0.0381 (7) | −0.0089 (6) | 0.0003 (6) | −0.0046 (6) |
C2B | 0.0365 (7) | 0.0524 (8) | 0.0360 (7) | −0.0047 (6) | −0.0034 (6) | −0.0022 (6) |
C3B | 0.0367 (6) | 0.0482 (8) | 0.0317 (7) | −0.0042 (6) | −0.0047 (5) | −0.0030 (6) |
C4B | 0.0388 (7) | 0.0464 (8) | 0.0463 (8) | −0.0010 (6) | −0.0074 (6) | −0.0056 (6) |
C5B | 0.0518 (8) | 0.0411 (8) | 0.0531 (9) | 0.0001 (6) | −0.0081 (7) | −0.0029 (7) |
C6B | 0.0498 (8) | 0.0462 (8) | 0.0434 (8) | −0.0130 (6) | −0.0006 (6) | −0.0042 (6) |
C7B | 0.0361 (7) | 0.0604 (9) | 0.0500 (9) | −0.0069 (6) | −0.0039 (6) | 0.0025 (7) |
C8B | 0.0377 (7) | 0.0495 (8) | 0.0496 (8) | −0.0004 (6) | −0.0049 (6) | 0.0066 (6) |
Cl—C2 | 1.7439 (15) | C3A—C8A | 1.379 (2) |
Cl1A—C6A | 1.7368 (16) | C4A—C5A | 1.374 (2) |
Cl1B—C6B | 1.7380 (15) | C4A—H4AA | 0.9300 |
O1A—C2A | 1.2156 (16) | C5A—C6A | 1.366 (2) |
O1B—C2B | 1.2173 (15) | C5A—H5AA | 0.9300 |
C—C1 | 1.5183 (18) | C6A—C7A | 1.370 (2) |
C—C1A | 1.5285 (18) | C7A—C8A | 1.382 (2) |
C—C1B | 1.5450 (19) | C7A—H7AA | 0.9300 |
C—H0A | 0.9800 | C8A—H8AA | 0.9300 |
C1—C6 | 1.3759 (19) | C1B—C2B | 1.5042 (19) |
C1—C2 | 1.3976 (18) | C1B—H1BA | 0.9700 |
C2—C3 | 1.379 (2) | C1B—H1BB | 0.9700 |
C3—C4 | 1.364 (3) | C2B—C3B | 1.4831 (19) |
C3—H3A | 0.9300 | C3B—C4B | 1.3910 (19) |
C4—C5 | 1.370 (3) | C3B—C8B | 1.3972 (18) |
C4—H4A | 0.9300 | C4B—C5B | 1.371 (2) |
C5—C6 | 1.386 (2) | C4B—H4BA | 0.9300 |
C5—H5A | 0.9300 | C5B—C6B | 1.378 (2) |
C6—H6A | 0.9300 | C5B—H5BA | 0.9300 |
C1A—C2A | 1.504 (2) | C6B—C7B | 1.372 (2) |
C1A—H1AA | 0.9700 | C7B—C8B | 1.374 (2) |
C1A—H1AB | 0.9700 | C7B—H7BA | 0.9300 |
C2A—C3A | 1.488 (2) | C8B—H8BA | 0.9300 |
C3A—C4A | 1.375 (2) | ||
C1—C—C1A | 112.96 (11) | C6A—C5A—C4A | 119.09 (15) |
C1—C—C1B | 107.79 (11) | C6A—C5A—H5AA | 120.5 |
C1A—C—C1B | 110.64 (10) | C4A—C5A—H5AA | 120.5 |
C1—C—H0A | 108.4 | C5A—C6A—C7A | 121.53 (14) |
C1A—C—H0A | 108.4 | C5A—C6A—Cl1A | 120.38 (13) |
C1B—C—H0A | 108.4 | C7A—C6A—Cl1A | 118.08 (13) |
C6—C1—C2 | 115.99 (13) | C6A—C7A—C8A | 118.44 (15) |
C6—C1—C | 121.92 (12) | C6A—C7A—H7AA | 120.8 |
C2—C1—C | 121.97 (12) | C8A—C7A—H7AA | 120.8 |
C3—C2—C1 | 122.17 (14) | C3A—C8A—C7A | 121.32 (14) |
C3—C2—Cl | 117.63 (12) | C3A—C8A—H8AA | 119.3 |
C1—C2—Cl | 120.19 (11) | C7A—C8A—H8AA | 119.3 |
C4—C3—C2 | 119.73 (16) | C2B—C1B—C | 114.25 (11) |
C4—C3—H3A | 120.1 | C2B—C1B—H1BA | 108.7 |
C2—C3—H3A | 120.1 | C—C1B—H1BA | 108.7 |
C3—C4—C5 | 120.13 (16) | C2B—C1B—H1BB | 108.7 |
C3—C4—H4A | 119.9 | C—C1B—H1BB | 108.7 |
C5—C4—H4A | 119.9 | H1BA—C1B—H1BB | 107.6 |
C4—C5—C6 | 119.39 (16) | O1B—C2B—C3B | 120.07 (12) |
C4—C5—H5A | 120.3 | O1B—C2B—C1B | 119.50 (13) |
C6—C5—H5A | 120.3 | C3B—C2B—C1B | 120.43 (11) |
C1—C6—C5 | 122.57 (15) | C4B—C3B—C8B | 118.21 (13) |
C1—C6—H6A | 118.7 | C4B—C3B—C2B | 119.49 (11) |
C5—C6—H6A | 118.7 | C8B—C3B—C2B | 122.30 (12) |
C2A—C1A—C | 114.47 (11) | C5B—C4B—C3B | 121.13 (12) |
C2A—C1A—H1AA | 108.6 | C5B—C4B—H4BA | 119.4 |
C—C1A—H1AA | 108.6 | C3B—C4B—H4BA | 119.4 |
C2A—C1A—H1AB | 108.6 | C4B—C5B—C6B | 119.10 (13) |
C—C1A—H1AB | 108.6 | C4B—C5B—H5BA | 120.5 |
H1AA—C1A—H1AB | 107.6 | C6B—C5B—H5BA | 120.5 |
O1A—C2A—C3A | 121.13 (13) | C7B—C6B—C5B | 121.52 (13) |
O1A—C2A—C1A | 120.22 (13) | C7B—C6B—Cl1B | 119.20 (11) |
C3A—C2A—C1A | 118.61 (12) | C5B—C6B—Cl1B | 119.28 (11) |
C4A—C3A—C8A | 118.37 (13) | C6B—C7B—C8B | 119.09 (13) |
C4A—C3A—C2A | 119.48 (13) | C6B—C7B—H7BA | 120.5 |
C8A—C3A—C2A | 122.15 (12) | C8B—C7B—H7BA | 120.5 |
C5A—C4A—C3A | 121.23 (15) | C7B—C8B—C3B | 120.94 (13) |
C5A—C4A—H4AA | 119.4 | C7B—C8B—H8BA | 119.5 |
C3A—C4A—H4AA | 119.4 | C3B—C8B—H8BA | 119.5 |
C1A—C—C1—C6 | 38.87 (18) | C4A—C5A—C6A—C7A | 1.0 (3) |
C1B—C—C1—C6 | −83.68 (15) | C4A—C5A—C6A—Cl1A | −179.63 (14) |
C1A—C—C1—C2 | −145.14 (12) | C5A—C6A—C7A—C8A | −0.9 (3) |
C1B—C—C1—C2 | 92.31 (14) | Cl1A—C6A—C7A—C8A | 179.71 (13) |
C6—C1—C2—C3 | −0.3 (2) | C4A—C3A—C8A—C7A | 1.4 (2) |
C—C1—C2—C3 | −176.50 (13) | C2A—C3A—C8A—C7A | −177.85 (15) |
C6—C1—C2—Cl | 178.12 (11) | C6A—C7A—C8A—C3A | −0.3 (3) |
C—C1—C2—Cl | 1.90 (18) | C1—C—C1B—C2B | −177.57 (10) |
C1—C2—C3—C4 | −0.5 (2) | C1A—C—C1B—C2B | 58.46 (15) |
Cl—C2—C3—C4 | −178.91 (13) | C—C1B—C2B—O1B | −95.04 (15) |
C2—C3—C4—C5 | 0.3 (3) | C—C1B—C2B—C3B | 84.40 (14) |
C3—C4—C5—C6 | 0.7 (3) | O1B—C2B—C3B—C4B | −4.2 (2) |
C2—C1—C6—C5 | 1.3 (2) | C1B—C2B—C3B—C4B | 176.39 (11) |
C—C1—C6—C5 | 177.49 (14) | O1B—C2B—C3B—C8B | 176.04 (13) |
C4—C5—C6—C1 | −1.5 (3) | C1B—C2B—C3B—C8B | −3.40 (19) |
C1—C—C1A—C2A | 67.11 (15) | C8B—C3B—C4B—C5B | 0.7 (2) |
C1B—C—C1A—C2A | −171.94 (11) | C2B—C3B—C4B—C5B | −179.14 (13) |
C—C1A—C2A—O1A | 12.0 (2) | C3B—C4B—C5B—C6B | −0.9 (2) |
C—C1A—C2A—C3A | −170.18 (12) | C4B—C5B—C6B—C7B | 0.1 (2) |
O1A—C2A—C3A—C4A | 1.4 (2) | C4B—C5B—C6B—Cl1B | 179.99 (11) |
C1A—C2A—C3A—C4A | −176.42 (14) | C5B—C6B—C7B—C8B | 1.1 (2) |
O1A—C2A—C3A—C8A | −179.32 (16) | Cl1B—C6B—C7B—C8B | −178.87 (11) |
C1A—C2A—C3A—C8A | 2.9 (2) | C6B—C7B—C8B—C3B | −1.3 (2) |
C8A—C3A—C4A—C5A | −1.4 (3) | C4B—C3B—C8B—C7B | 0.5 (2) |
C2A—C3A—C4A—C5A | 177.96 (16) | C2B—C3B—C8B—C7B | −179.73 (13) |
C3A—C4A—C5A—C6A | 0.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AA···O1Ai | 0.93 | 2.50 | 3.306 (2) | 145 |
C7B—H7BA···O1Bii | 0.93 | 2.51 | 3.2917 (17) | 142 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C23H17Cl3O2 |
Mr | 431.72 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.1717 (8), 7.7000 (15), 18.901 (6) |
α, β, γ (°) | 85.88 (2), 83.518 (15), 77.656 (12) |
V (Å3) | 1011.9 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.47 |
Crystal size (mm) | 0.45 × 0.39 × 0.28 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.712, 0.877 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14729, 6690, 3147 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.759 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.118, 0.93 |
No. of reflections | 6690 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.33 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis PRO, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C7A—H7AA···O1Ai | 0.93 | 2.50 | 3.306 (2) | 145.3 |
C7B—H7BA···O1Bii | 0.93 | 2.51 | 3.2917 (17) | 142.4 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
1,5-Diketones are important synthetic intermediates and starting materials in the synthesis of many heterocyclic compounds (Hirsch & Bailey, 1978; Krohnke, 1976). The structures of related compounds viz., 1,5-bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione (Insuasty et al. 2006), 1,5-(4-dichlorophenyl)-3-(2,5-dimethoxyphenyl)pentane-1,5-dione (Teh et al. 2006), 3-(2-furyl)-1,5-bis(4-methylphenyl)pentane-1,5-dione (Huang et al. 2006), 1,5-bis(4-chlorophenyl)-3-(4-pyridyl)pentane-1,5dione (Qiu et al. 2006a), 3-(3-chlorophenyl)-1,5-bis(4-nitrophenyl)pentane-1,5-dione (Qiu et al. 2006b), 1,5-bis (3-bromothien-2-yl) -3- (2,3,5-trichlorophenyl)pentane-1,5-dione, (Butcher et al. 2007), 1,5-bis(3-bromo-2-thienyl)-3-(3-nitrophenyl)pentane-1,5-dione (Yathirajan et al. 2006), 1,5-bis(4-bromophenyl)-3-(3-nitrophenyl)pentane-1,5-dione, (Yathirajan et al. 2007) have been reported. A new 1,5-dione, (I), C23H17Cl3O2 was synthesized and the crystal structure is reported here.
In the title compound, C23H17Cl3O2, the dihedral angles between the 2-chlorophenyl group and the two 4-chlorophenyl groups are 88.9 (3) and 12.9 (2)°, while the angle between the mean planes of the two 4-chlorophenyl groups is 77.9 (5)° (Fig. 1). The crystal packing is stabilized by intermolecular C–H···O interactions between a hydrogen atom from each of the two the two 4-chlorophenyl groups and its nearby ketone oxygen in neighboring molecules which link the molecules into chains diagonally and oblique along the ac plane of the unit cell (Fig. 2). Additional intermolecular π-π stacking interactions occur between adjacent 2-chlorophenyl rings [Cg3 = center of gravity of the 4-chlorolphenyl ring (C3B–C8B); Cg3···Cg3 = 3.931 (6) Å; 1 - x, 1 - y, -z] as well as between one of the 4-chlorophenyl rings and a 2-chlorophenyl ring [Cg1 = center of gravity of the 2-chlorolphenyl ring (C1–C6); Cg1···Cg3 = 3.931 (6) Å; x, -1 + y, z].