1-(4-Chloro­phen­yl)-3-(2,4,5-trimethoxy­phen­yl)prop-2-en-1-one

The title mol­ecule, C₁₈H₁₇ClO₄, is slightly distorted from planarity. The dihedral angle between the two benzene rings is 11.6 (2)°. The crystal packing is stabilized by C—H...π inter­actions and van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.058
• wR factor = 0.139
• Data-to-parameter ratio = 22.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C2     -   C3      ..       5.63 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

Alert level G
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           29.99
           From the CIF: _reflns_number_total               4783
           Count of symmetry unique reflns         2737
           Completeness (_total/calc)            174.75%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2046
           Fraction of Friedel pairs measured     0.748
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 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
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

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).

1-(4-Chlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

Crystal data

C18H17ClO4	F(000) = 696
Mr = 332.77	Dx = 1.345 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1384 reflections
a = 7.0295 (4) Å	θ = 1.8–30.0°
b = 10.5127 (6) Å	µ = 0.25 mm^−1
c = 22.2438 (13) Å	T = 297 K
V = 1643.80 (16) Å^3	Needle, yellow
Z = 4	0.53 × 0.11 × 0.08 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4783 independent reflections
Radiation source: fine-focus sealed tube	2062 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 8.33 pixels mm^-1	θmax = 30.0°, θmin = 1.8°
ω scans	h = −9→5
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
Tmin = 0.825, Tmax = 0.981	l = −31→27
15298 measured reflections

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)] = 0.058	H-atom parameters constrained
wR(F^2) = 0.139	w = 1/[σ^2(Fo^2) + (0.0401P)^2 + 0.2277P] where P = (Fo^2 + 2Fc^2)/3
S = 0.99	(Δ/σ)max = 0.001
4783 reflections	Δρmax = 0.13 e Å^−3
211 parameters	Δρmin = −0.18 e Å^−3
0 restraints	Absolute structure: Flack (1983), 2050 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.21 (11)

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
Cl1	−0.26140 (16)	0.48191 (9)	0.47963 (5)	0.0977 (4)
O1	0.5069 (4)	0.4355 (2)	0.30665 (12)	0.0860 (8)
O2	1.0309 (4)	0.1832 (2)	0.25799 (10)	0.0713 (7)
O3	1.2316 (3)	−0.18182 (19)	0.37441 (10)	0.0658 (6)
O4	0.9358 (3)	−0.1624 (2)	0.44168 (10)	0.0648 (6)
C1	0.1752 (5)	0.4960 (3)	0.36676 (15)	0.0643 (9)
H1A	0.2221	0.5528	0.3383	0.077*
C2	0.0129 (5)	0.5264 (3)	0.39829 (15)	0.0652 (9)
H2A	−0.0479	0.6038	0.3918	0.078*
C3	−0.0580 (5)	0.4419 (3)	0.43908 (15)	0.0606 (9)
C4	0.0293 (5)	0.3268 (3)	0.44904 (16)	0.0664 (10)
H4A	−0.0214	0.2691	0.4764	0.080*
C5	0.1928 (5)	0.2984 (3)	0.41793 (15)	0.0588 (9)
H5A	0.2530	0.2210	0.4248	0.071*
C6	0.2701 (5)	0.3822 (3)	0.37668 (13)	0.0500 (8)
C7	0.4508 (5)	0.3583 (3)	0.34412 (15)	0.0578 (8)
C8	0.5614 (5)	0.2430 (3)	0.35685 (15)	0.0565 (8)
H8A	0.5133	0.1843	0.3841	0.068*
C9	0.7279 (5)	0.2196 (3)	0.33082 (14)	0.0579 (9)
H9A	0.7685	0.2795	0.3029	0.070*
C10	0.8542 (4)	0.1128 (3)	0.34038 (14)	0.0492 (8)
C11	0.8272 (4)	0.0244 (3)	0.38744 (13)	0.0514 (8)
H11A	0.7213	0.0323	0.4122	0.062*
C12	0.9527 (5)	−0.0724 (3)	0.39745 (13)	0.0494 (8)
C13	1.1147 (4)	−0.0841 (3)	0.36000 (14)	0.0515 (8)
C14	1.1403 (4)	−0.0005 (3)	0.31363 (14)	0.0518 (8)
H14A	1.2447	−0.0098	0.2884	0.062*
C15	1.0132 (5)	0.0977 (3)	0.30375 (14)	0.0529 (8)
C16	1.2049 (5)	0.1882 (4)	0.22658 (16)	0.0764 (11)
H16A	1.2047	0.2602	0.2000	0.115*
H16B	1.2206	0.1116	0.2036	0.115*
H16D	1.3077	0.1961	0.2547	0.115*
C17	1.4019 (5)	−0.1956 (4)	0.34027 (17)	0.0792 (12)
H17A	1.4724	−0.2674	0.3549	0.119*
H17D	1.4777	−0.1201	0.3442	0.119*
H17B	1.3704	−0.2085	0.2987	0.119*
C18	0.7864 (5)	−0.1465 (3)	0.48419 (15)	0.0731 (10)
H18D	0.7954	−0.2115	0.5144	0.110*
H18A	0.6660	−0.1531	0.4641	0.110*
H18B	0.7971	−0.0644	0.5027	0.110*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0829 (7)	0.0892 (7)	0.1210 (9)	0.0233 (6)	0.0345 (7)	0.0023 (6)
O1	0.0839 (19)	0.0756 (16)	0.0983 (19)	0.0141 (15)	0.0305 (17)	0.0307 (15)
O2	0.0654 (15)	0.0813 (15)	0.0671 (15)	0.0082 (14)	0.0207 (14)	0.0226 (13)
O3	0.0616 (15)	0.0645 (13)	0.0712 (16)	0.0190 (13)	0.0193 (14)	0.0061 (12)
O4	0.0725 (16)	0.0614 (13)	0.0605 (13)	0.0129 (13)	0.0200 (13)	0.0087 (11)
C1	0.074 (2)	0.0547 (19)	0.064 (2)	0.009 (2)	0.007 (2)	0.0076 (17)
C2	0.074 (2)	0.0558 (18)	0.066 (2)	0.016 (2)	−0.001 (2)	0.0067 (17)
C3	0.054 (2)	0.066 (2)	0.063 (2)	0.0107 (18)	0.0000 (19)	−0.0146 (18)
C4	0.066 (2)	0.0536 (19)	0.080 (2)	0.006 (2)	0.011 (2)	0.0053 (17)
C5	0.055 (2)	0.0530 (18)	0.068 (2)	0.0105 (17)	0.0054 (19)	0.0010 (16)
C6	0.0533 (19)	0.0466 (15)	0.0500 (18)	−0.0010 (16)	−0.0029 (17)	−0.0015 (14)
C7	0.060 (2)	0.0532 (18)	0.060 (2)	−0.0009 (18)	0.0050 (19)	0.0011 (17)
C8	0.056 (2)	0.0527 (17)	0.060 (2)	0.0014 (17)	0.0064 (19)	0.0027 (16)
C9	0.055 (2)	0.0627 (19)	0.056 (2)	0.0038 (19)	0.0046 (19)	0.0029 (15)
C10	0.0462 (18)	0.0524 (17)	0.0489 (18)	0.0017 (16)	0.0016 (17)	−0.0001 (15)
C11	0.0434 (16)	0.0587 (18)	0.0519 (18)	−0.0033 (16)	0.0117 (16)	−0.0033 (15)
C12	0.0529 (19)	0.0509 (16)	0.0444 (17)	0.0014 (17)	0.0077 (18)	0.0010 (14)
C13	0.051 (2)	0.0499 (17)	0.0532 (19)	0.0048 (16)	0.0053 (18)	−0.0036 (16)
C14	0.0474 (17)	0.0609 (19)	0.0472 (18)	0.0040 (17)	0.0125 (16)	0.0002 (16)
C15	0.054 (2)	0.0584 (18)	0.0460 (18)	−0.0048 (18)	0.0052 (18)	0.0025 (15)
C16	0.060 (2)	0.110 (3)	0.059 (2)	−0.010 (2)	0.013 (2)	0.020 (2)
C17	0.056 (2)	0.092 (3)	0.090 (3)	0.022 (2)	0.021 (2)	0.002 (2)
C18	0.078 (3)	0.077 (2)	0.063 (2)	0.005 (2)	0.029 (2)	0.0102 (19)

Geometric parameters (Å, º)

Cl1—C3	1.742 (3)	C8—H8A	0.93
O1—C7	1.228 (4)	C9—C10	1.447 (4)
O2—C15	1.364 (3)	C9—H9A	0.93
O2—C16	1.409 (4)	C10—C15	1.392 (4)
O3—C13	1.355 (3)	C10—C11	1.413 (4)
O3—C17	1.425 (4)	C11—C12	1.365 (4)
O4—C12	1.370 (3)	C11—H11A	0.93
O4—C18	1.423 (4)	C12—C13	1.416 (4)
C1—C2	1.377 (4)	C13—C14	1.367 (4)
C1—C6	1.388 (4)	C14—C15	1.382 (4)
C1—H1A	0.93	C14—H14A	0.93
C2—C3	1.364 (5)	C16—H16A	0.96
C2—H2A	0.93	C16—H16B	0.96
C3—C4	1.374 (4)	C16—H16D	0.96
C4—C5	1.374 (4)	C17—H17A	0.96
C4—H4A	0.93	C17—H17D	0.96
C5—C6	1.383 (4)	C17—H17B	0.96
C5—H5A	0.93	C18—H18D	0.96
C6—C7	1.484 (5)	C18—H18A	0.96
C7—C8	1.467 (4)	C18—H18B	0.96
C8—C9	1.329 (4)
C15—O2—C16	118.3 (3)	C12—C11—C10	121.6 (3)
C13—O3—C17	117.4 (3)	C12—C11—H11A	119.2
C12—O4—C18	117.4 (2)	C10—C11—H11A	119.2
C2—C1—C6	121.1 (3)	C11—C12—O4	125.2 (3)
C2—C1—H1A	119.4	C11—C12—C13	119.2 (3)
C6—C1—H1A	119.4	O4—C12—C13	115.6 (3)
C3—C2—C1	119.4 (3)	O3—C13—C14	125.9 (3)
C3—C2—H2A	120.3	O3—C13—C12	114.5 (3)
C1—C2—H2A	120.3	C14—C13—C12	119.6 (3)
C2—C3—C4	121.2 (3)	C13—C14—C15	121.0 (3)
C2—C3—Cl1	119.1 (3)	C13—C14—H14A	119.5
C4—C3—Cl1	119.7 (3)	C15—C14—H14A	119.5
C5—C4—C3	118.9 (3)	O2—C15—C14	123.5 (3)
C5—C4—H4A	120.6	O2—C15—C10	115.8 (3)
C3—C4—H4A	120.6	C14—C15—C10	120.7 (3)
C4—C5—C6	121.6 (3)	O2—C16—H16A	109.5
C4—C5—H5A	119.2	O2—C16—H16B	109.5
C6—C5—H5A	119.2	H16A—C16—H16B	109.5
C5—C6—C1	117.8 (3)	O2—C16—H16D	109.5
C5—C6—C7	123.5 (3)	H16A—C16—H16D	109.5
C1—C6—C7	118.7 (3)	H16B—C16—H16D	109.5
O1—C7—C8	120.4 (3)	O3—C17—H17A	109.5
O1—C7—C6	119.6 (3)	O3—C17—H17D	109.5
C8—C7—C6	120.0 (3)	H17A—C17—H17D	109.5
C9—C8—C7	122.4 (3)	O3—C17—H17B	109.5
C9—C8—H8A	118.8	H17A—C17—H17B	109.5
C7—C8—H8A	118.8	H17D—C17—H17B	109.5
C8—C9—C10	128.3 (3)	O4—C18—H18D	109.5
C8—C9—H9A	115.8	O4—C18—H18A	109.5
C10—C9—H9A	115.8	H18D—C18—H18A	109.5
C15—C10—C11	117.8 (3)	O4—C18—H18B	109.5
C15—C10—C9	119.7 (3)	H18D—C18—H18B	109.5
C11—C10—C9	122.5 (3)	H18A—C18—H18B	109.5
C6—C1—C2—C3	−1.4 (5)	C10—C11—C12—O4	−179.4 (3)
C1—C2—C3—C4	−0.3 (5)	C10—C11—C12—C13	0.4 (4)
C1—C2—C3—Cl1	179.0 (3)	C18—O4—C12—C11	−6.6 (4)
C2—C3—C4—C5	1.2 (5)	C18—O4—C12—C13	173.6 (3)
Cl1—C3—C4—C5	−178.1 (3)	C17—O3—C13—C14	3.4 (5)
C3—C4—C5—C6	−0.6 (5)	C17—O3—C13—C12	−177.2 (3)
C4—C5—C6—C1	−1.0 (5)	C11—C12—C13—O3	178.9 (3)
C4—C5—C6—C7	177.1 (3)	O4—C12—C13—O3	−1.3 (4)
C2—C1—C6—C5	2.0 (5)	C11—C12—C13—C14	−1.6 (4)
C2—C1—C6—C7	−176.2 (3)	O4—C12—C13—C14	178.2 (3)
C5—C6—C7—O1	177.6 (3)	O3—C13—C14—C15	−178.7 (3)
C1—C6—C7—O1	−4.3 (5)	C12—C13—C14—C15	1.9 (4)
C5—C6—C7—C8	−2.5 (5)	C16—O2—C15—C14	−13.0 (5)
C1—C6—C7—C8	175.6 (3)	C16—O2—C15—C10	168.3 (3)
O1—C7—C8—C9	2.7 (5)	C13—C14—C15—O2	−179.5 (3)
C6—C7—C8—C9	−177.2 (3)	C13—C14—C15—C10	−0.9 (5)
C7—C8—C9—C10	177.9 (3)	C11—C10—C15—O2	178.4 (3)
C8—C9—C10—C15	172.8 (3)	C9—C10—C15—O2	−4.0 (4)
C8—C9—C10—C11	−9.7 (5)	C11—C10—C15—C14	−0.3 (4)
C15—C10—C11—C12	0.5 (4)	C9—C10—C15—C14	177.2 (3)
C9—C10—C11—C12	−176.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···Cg1^i	0.96	2.89	3.672 (4)	139

Symmetry code: (i) x+1/2, −y+1/2, −z+1.