1-(4-Chloro­phenyl)-3-(4-hydroxy­phenyl)prop-2-en-1-one

In the title mol­ecule, C₁₅H₁₁ClO₂, the ketone group is in the s-cis conformation with respect to the olefinic double bond. The two aromatic rings form a dihedral angle of 26.07 (8)°. Screw-related mol­ecules are linked via O—H...O hydrogen bonds, forming a chain along the c axis. Weak C—H...O and C—H...Cl interactions interconnect the chains into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.108
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT480_ALERT_4_B Long H...A H-Bond Reported H2A    ..  O1      ..       2.99 Ang.

Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature         293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature ....        293
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  O2      ..       2.97 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H1     ..  CL1     ..       2.89 Ang.
PLAT482_ALERT_4_C Small D-H..A Angle Rep for C15    ..  O1      ..      98.00 Deg.

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           28.26
           From the CIF: _reflns_number_total               2846
           Count of symmetry unique reflns         1847
           Completeness (_total/calc)            154.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured       999
           Fraction of Friedel pairs measured     0.541
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

1-(4-chlorophenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Crystal data

C15H11ClO2	F(000) = 536
Mr = 258.69	Dx = 1.381 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2214 reflections
a = 4.0781 (6) Å	θ = 5.0–45.2°
b = 16.344 (3) Å	µ = 0.30 mm^−1
c = 18.664 (3) Å	T = 293 K
V = 1244.0 (4) Å^3	Needle, colourless
Z = 4	0.41 × 0.15 × 0.11 mm

Data collection

Siemens SMART CCD area-detector diffractometer	2846 independent reflections
Radiation source: fine-focus sealed tube	2294 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→4
Tmin = 0.889, Tmax = 0.968	k = −20→21
7590 measured reflections	l = −23→23

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)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.108	w = 1/[σ^2(Fo^2) + (0.0506P)^2 + 0.0833P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.001
2846 reflections	Δρmax = 0.21 e Å^−3
163 parameters	Δρmin = −0.13 e Å^−3
0 restraints	Absolute structure: Flack (1983), 1078 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (8)

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	0.85257 (19)	0.84317 (4)	0.92842 (3)	0.0843 (2)
O1	0.1540 (5)	0.52890 (9)	0.76206 (8)	0.0738 (5)
O2	−0.3645 (5)	0.60045 (9)	0.33115 (7)	0.0744 (5)
H2	−0.4502	0.5587	0.3155	0.112*
C1	−0.3280 (6)	0.51951 (11)	0.51290 (10)	0.0514 (5)
H1	−0.4021	0.4747	0.5390	0.062*
C2	−0.4084 (6)	0.52512 (11)	0.44107 (10)	0.0520 (5)
H2A	−0.5362	0.4849	0.4196	0.062*
C3	−0.2978 (6)	0.59069 (11)	0.40174 (11)	0.0531 (5)
C4	−0.1120 (6)	0.65100 (11)	0.43492 (10)	0.0542 (5)
H4	−0.0377	0.6956	0.4086	0.065*
C5	−0.0380 (5)	0.64492 (12)	0.50632 (11)	0.0520 (5)
H5	0.0837	0.6862	0.5280	0.062*
C6	−0.1408 (5)	0.57840 (11)	0.54721 (9)	0.0464 (4)
C7	−0.0534 (5)	0.56794 (12)	0.62220 (10)	0.0517 (5)
H7	−0.1329	0.5210	0.6443	0.062*
C8	0.1247 (6)	0.61686 (12)	0.66276 (10)	0.0532 (5)
H8	0.1982	0.6661	0.6436	0.064*
C9	0.2111 (5)	0.59648 (12)	0.73697 (10)	0.0528 (5)
C10	0.3758 (5)	0.65947 (12)	0.78216 (9)	0.0487 (5)
C11	0.3815 (6)	0.74222 (12)	0.76456 (10)	0.0559 (5)
H11	0.2861	0.7596	0.7219	0.067*
C12	0.5259 (7)	0.79865 (13)	0.80911 (11)	0.0626 (6)
H12	0.5254	0.8539	0.7972	0.075*
C13	0.6710 (6)	0.77240 (13)	0.87142 (11)	0.0572 (5)
C14	0.6721 (6)	0.69064 (14)	0.89021 (11)	0.0598 (6)
H14	0.7713	0.6735	0.9325	0.072*
C15	0.5255 (6)	0.63548 (14)	0.84570 (10)	0.0560 (5)
H15	0.5256	0.5804	0.8582	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0816 (5)	0.0946 (4)	0.0766 (4)	0.0121 (4)	−0.0116 (4)	−0.0324 (3)
O1	0.0979 (14)	0.0634 (8)	0.0602 (9)	−0.0125 (11)	0.0022 (10)	0.0159 (7)
O2	0.1108 (14)	0.0621 (8)	0.0503 (8)	−0.0149 (11)	−0.0153 (10)	0.0011 (7)
C1	0.0540 (12)	0.0448 (10)	0.0555 (11)	−0.0020 (10)	0.0082 (10)	0.0007 (8)
C2	0.0566 (13)	0.0444 (9)	0.0551 (11)	−0.0024 (10)	−0.0017 (10)	−0.0099 (8)
C3	0.0653 (14)	0.0442 (10)	0.0498 (11)	0.0071 (10)	−0.0027 (10)	−0.0050 (9)
C4	0.0687 (14)	0.0412 (9)	0.0528 (11)	−0.0035 (10)	−0.0026 (11)	0.0029 (8)
C5	0.0591 (12)	0.0437 (10)	0.0532 (11)	−0.0038 (10)	−0.0014 (10)	−0.0030 (9)
C6	0.0464 (11)	0.0444 (9)	0.0485 (10)	0.0023 (9)	0.0054 (9)	−0.0030 (8)
C7	0.0544 (13)	0.0515 (10)	0.0491 (11)	0.0018 (10)	0.0107 (9)	0.0047 (9)
C8	0.0613 (13)	0.0529 (10)	0.0454 (10)	−0.0038 (11)	0.0040 (10)	0.0039 (8)
C9	0.0547 (13)	0.0569 (11)	0.0469 (10)	0.0031 (10)	0.0078 (9)	0.0097 (9)
C10	0.0471 (11)	0.0614 (11)	0.0375 (9)	0.0049 (11)	0.0079 (9)	0.0043 (8)
C11	0.0676 (15)	0.0595 (11)	0.0405 (9)	0.0106 (12)	−0.0008 (10)	0.0064 (9)
C12	0.0787 (17)	0.0544 (11)	0.0548 (12)	0.0109 (12)	0.0013 (12)	−0.0009 (10)
C13	0.0530 (12)	0.0702 (12)	0.0484 (10)	0.0119 (12)	0.0043 (10)	−0.0125 (10)
C14	0.0564 (13)	0.0818 (14)	0.0414 (11)	0.0132 (13)	0.0021 (10)	0.0042 (10)
C15	0.0588 (13)	0.0632 (12)	0.0461 (11)	0.0081 (11)	0.0028 (10)	0.0123 (10)

Geometric parameters (Å, º)

Cl1—C13	1.737 (2)	C7—C8	1.319 (3)
O1—C9	1.222 (2)	C7—H7	0.93
O2—C3	1.355 (2)	C8—C9	1.467 (3)
O2—H2	0.82	C8—H8	0.93
C1—C2	1.383 (3)	C9—C10	1.491 (3)
C1—C6	1.385 (3)	C10—C15	1.390 (3)
C1—H1	0.93	C10—C11	1.392 (3)
C2—C3	1.375 (3)	C11—C12	1.374 (3)
C2—H2A	0.93	C11—H11	0.93
C3—C4	1.389 (3)	C12—C13	1.373 (3)
C4—C5	1.370 (3)	C12—H12	0.93
C4—H4	0.93	C13—C14	1.381 (3)
C5—C6	1.393 (3)	C14—C15	1.364 (3)
C5—H5	0.93	C14—H14	0.93
C6—C7	1.454 (3)	C15—H15	0.93
C3—O2—H2	109.5	C7—C8—H8	118.8
C2—C1—C6	122.18 (18)	C9—C8—H8	118.8
C2—C1—H1	118.9	O1—C9—C8	121.4 (2)
C6—C1—H1	118.9	O1—C9—C10	119.55 (18)
C3—C2—C1	119.42 (19)	C8—C9—C10	119.04 (16)
C3—C2—H2A	120.3	C15—C10—C11	117.9 (2)
C1—C2—H2A	120.3	C15—C10—C9	119.05 (18)
O2—C3—C2	123.02 (18)	C11—C10—C9	123.03 (18)
O2—C3—C4	117.37 (18)	C12—C11—C10	121.09 (19)
C2—C3—C4	119.61 (18)	C12—C11—H11	119.5
C5—C4—C3	120.17 (18)	C10—C11—H11	119.5
C5—C4—H4	119.9	C13—C12—C11	119.2 (2)
C3—C4—H4	119.9	C13—C12—H12	120.4
C4—C5—C6	121.55 (19)	C11—C12—H12	120.4
C4—C5—H5	119.2	C12—C13—C14	121.2 (2)
C6—C5—H5	119.2	C12—C13—Cl1	119.61 (17)
C1—C6—C5	117.05 (17)	C14—C13—Cl1	119.14 (17)
C1—C6—C7	119.88 (17)	C15—C14—C13	118.89 (19)
C5—C6—C7	123.05 (18)	C15—C14—H14	120.6
C8—C7—C6	128.03 (18)	C13—C14—H14	120.6
C8—C7—H7	116.0	C14—C15—C10	121.7 (2)
C6—C7—H7	116.0	C14—C15—H15	119.1
C7—C8—C9	122.44 (18)	C10—C15—H15	119.1
C6—C1—C2—C3	0.6 (3)	O1—C9—C10—C15	14.0 (3)
C1—C2—C3—O2	179.7 (2)	C8—C9—C10—C15	−165.2 (2)
C1—C2—C3—C4	−1.1 (3)	O1—C9—C10—C11	−164.5 (2)
O2—C3—C4—C5	179.6 (2)	C8—C9—C10—C11	16.2 (3)
C2—C3—C4—C5	0.4 (3)	C15—C10—C11—C12	−1.0 (3)
C3—C4—C5—C6	1.0 (3)	C9—C10—C11—C12	177.6 (2)
C2—C1—C6—C5	0.7 (3)	C10—C11—C12—C13	1.0 (4)
C2—C1—C6—C7	−177.8 (2)	C11—C12—C13—C14	−0.4 (4)
C4—C5—C6—C1	−1.5 (3)	C11—C12—C13—Cl1	−179.68 (17)
C4—C5—C6—C7	176.9 (2)	C12—C13—C14—C15	−0.1 (4)
C1—C6—C7—C8	179.1 (2)	Cl1—C13—C14—C15	179.16 (17)
C5—C6—C7—C8	0.8 (3)	C13—C14—C15—C10	0.1 (3)
C6—C7—C8—C9	−176.3 (2)	C11—C10—C15—C14	0.5 (3)
C7—C8—C9—O1	8.6 (4)	C9—C10—C15—C14	−178.2 (2)
C7—C8—C9—C10	−172.19 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1^i	0.82	1.93	2.743 (2)	169
C7—H7···O1	0.93	2.49	2.817 (2)	101
C15—H15···O1	0.93	2.50	2.787 (3)	98
C2—H2A···O1^i	0.93	2.99	3.598 (3)	125
C11—H11···O2^ii	0.93	2.57	3.288 (3)	135
C12—H12···O2^ii	0.93	2.97	3.480 (3)	116
C1—H1···Cl1^iii	0.93	2.89	3.753 (2)	154

Symmetry codes: (i) −x−1/2, −y+1, z−1/2; (ii) x+1/2, −y+3/2, −z+1; (iii) −x, y−1/2, −z+3/2.