1,5-Bis(4-chloro­phen­yl)penta-1,4-dien-3-one

The title compound, C₁₇H₁₂Cl₂O, shows significant non-linear optical activity. A twofold rotation axis passes through the carbonyl group.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.079
• wR factor = 0.245
• Data-to-parameter ratio = 22.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C3     -   C4      ..       7.14 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C4     -   C5      ..       8.64 su
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C1     -   C2     ...       1.58 Ang.
PLAT369_ALERT_2_B Long   C(sp2)-C(sp2) Bond  C1     -   C2_a   ...       1.58 Ang.

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.20
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1     -   C2      ..       6.13 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4     -   C9      ..       5.99 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C5     -   C6      ..       6.77 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           30.69
           From the CIF: _reflns_number_total               2063
           From the CIF: _diffrn_reflns_limit_ max hkl   33.    7.    8.
           From the CIF: _diffrn_reflns_limit_ min hkl  -32.   -7.   -8.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   35.    7.    8.
           Calculated minimum hkl  -35.   -7.   -8.
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           30.69
           From the CIF: _reflns_number_total               2063
           Count of symmetry unique reflns         1324
           Completeness (_total/calc)            155.82%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       739
           Fraction of Friedel pairs measured     0.558
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,5-Bis(4-chlorophenyl)penta-1,4-dien-3-one

Crystal data

C17H12Cl2O	Dx = 1.418 Mg m^−3
Mr = 303.17	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 3962 reflections
a = 24.509 (3) Å	θ = 2.5–28.0°
b = 4.9846 (5) Å	µ = 0.45 mm^−1
c = 5.8103 (6) Å	T = 298 K
V = 709.82 (13) Å^3	Chunk, colorless
Z = 2	0.38 × 0.36 × 0.28 mm
F(000) = 312

Data collection

Bruker APEX2 CCD area-detector diffractometer	2063 independent reflections
Radiation source: fine-focus sealed tube	1630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 30.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −32→33
Tmin = 0.848, Tmax = 0.885	k = −7→7
7671 measured reflections	l = −8→8

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.079	H-atom parameters constrained
wR(F^2) = 0.245	w = 1/[σ^2(Fo^2) + (0.1266P)^2 + 0.4423P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.015
2063 reflections	Δρmax = 0.69 e Å^−3
92 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Absolute structure: Flack (1983), 739 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl	0.70645 (5)	−0.1178 (2)	0.9020 (2)	0.0778 (4)
O	0.5000	1.0000	0.0921 (17)	0.113 (2)
C1	0.5000	1.0000	0.293 (2)	0.085 (2)
C2	0.5352 (2)	0.8224 (10)	0.4625 (13)	0.0881 (17)
H2A	0.5276	0.8218	0.6193	0.106*
C3	0.5730 (2)	0.6840 (10)	0.3858 (10)	0.0755 (12)
H3A	0.5811	0.6973	0.2297	0.091*
C4	0.6067 (2)	0.4959 (10)	0.5294 (9)	0.0744 (13)
C5	0.58944 (17)	0.4057 (11)	0.7458 (11)	0.0793 (14)
H5A	0.5578	0.4749	0.8110	0.095*
C6	0.61997 (18)	0.2105 (9)	0.8650 (8)	0.0668 (10)
H6A	0.6087	0.1430	1.0064	0.080*
C7	0.66730 (16)	0.1251 (8)	0.7616 (7)	0.0590 (8)
C8	0.6837 (2)	0.2178 (10)	0.5527 (9)	0.0734 (12)
H8A	0.7159	0.1530	0.4886	0.088*
C9	0.6544 (2)	0.4011 (10)	0.4374 (8)	0.0745 (12)
H9A	0.6665	0.4637	0.2954	0.089*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl	0.0812 (7)	0.0616 (6)	0.0905 (8)	−0.0005 (5)	−0.0168 (6)	0.0082 (6)
O	0.090 (4)	0.102 (5)	0.146 (7)	0.008 (3)	0.000	0.000
C1	0.052 (3)	0.052 (3)	0.151 (8)	0.002 (3)	0.000	0.000
C2	0.075 (3)	0.061 (3)	0.128 (5)	−0.013 (2)	0.017 (3)	−0.021 (3)
C3	0.081 (3)	0.068 (3)	0.078 (3)	−0.007 (2)	0.008 (2)	−0.005 (2)
C4	0.091 (3)	0.052 (2)	0.080 (3)	−0.020 (2)	−0.031 (3)	0.011 (2)
C5	0.0491 (19)	0.078 (3)	0.111 (4)	−0.008 (2)	−0.005 (2)	−0.028 (3)
C6	0.064 (2)	0.070 (2)	0.067 (2)	−0.0094 (19)	0.0000 (18)	−0.0018 (19)
C7	0.065 (2)	0.0473 (16)	0.064 (2)	−0.0078 (17)	−0.0130 (16)	−0.0050 (17)
C8	0.082 (3)	0.067 (3)	0.071 (3)	−0.007 (2)	−0.002 (2)	−0.001 (2)
C9	0.083 (3)	0.071 (3)	0.070 (3)	−0.016 (2)	−0.005 (2)	0.014 (2)

Geometric parameters (Å, º)

Cl—C7	1.747 (4)	C4—C5	1.400 (8)
O—C1	1.170 (12)	C5—C6	1.410 (7)
C1—C2	1.579 (10)	C5—H5A	0.9300
C1—C2^i	1.579 (10)	C6—C7	1.374 (6)
C2—C3	1.239 (7)	C6—H6A	0.9300
C2—H2A	0.9300	C7—C8	1.360 (7)
C3—C4	1.502 (7)	C8—C9	1.342 (7)
C3—H3A	0.9300	C8—H8A	0.9300
C4—C9	1.371 (7)	C9—H9A	0.9300
O—C1—C2	128.5 (4)	C6—C5—H5A	119.9
O—C1—C2^i	128.5 (4)	C7—C6—C5	116.6 (5)
C2—C1—C2^i	103.1 (9)	C7—C6—H6A	121.7
C3—C2—C1	119.8 (7)	C5—C6—H6A	121.7
C3—C2—H2A	120.1	C8—C7—C6	122.4 (4)
C1—C2—H2A	120.1	C8—C7—Cl	119.3 (4)
C2—C3—C4	124.0 (6)	C6—C7—Cl	118.3 (3)
C2—C3—H3A	118.0	C9—C8—C7	121.2 (5)
C4—C3—H3A	118.0	C9—C8—H8A	119.4
C9—C4—C5	119.8 (4)	C7—C8—H8A	119.4
C9—C4—C3	117.9 (5)	C8—C9—C4	119.8 (5)
C5—C4—C3	122.3 (5)	C8—C9—H9A	120.1
C4—C5—C6	120.2 (5)	C4—C9—H9A	120.1
C4—C5—H5A	119.9
O—C1—C2—C3	9.8 (5)	C5—C6—C7—C8	−1.4 (6)
C2^i—C1—C2—C3	−170.2 (5)	C5—C6—C7—Cl	−179.7 (3)
C1—C2—C3—C4	−176.2 (4)	C6—C7—C8—C9	0.6 (7)
C2—C3—C4—C9	−165.6 (5)	Cl—C7—C8—C9	178.9 (4)
C2—C3—C4—C5	17.7 (7)	C7—C8—C9—C4	−0.7 (7)
C9—C4—C5—C6	−2.4 (7)	C5—C4—C9—C8	1.6 (7)
C3—C4—C5—C6	174.2 (4)	C3—C4—C9—C8	−175.2 (4)
C4—C5—C6—C7	2.3 (6)

Symmetry code: (i) −x+1, −y+2, z.