(2E)-3-(Biphenyl-4-yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

The title compound, C₂₂H₁₈O₂, was prepared from biphenyl-4-carbaldehyde and 4-methoxy­acetophenone. The mol­ecule deviates significantly from planarity.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.057
• wR factor = 0.145
• Data-to-parameter ratio = 8.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.29 su
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6

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           27.50
           From the CIF: _reflns_number_total               1843
           Count of symmetry unique reflns         1872
           Completeness (_total/calc)             98.45%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   1 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: COLLECT (Nonius, 1999); cell refinement: DIRAX/LSQ (Duisenberg, 1992); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2007).

(2E)-3-(Biphenyl-3-yl)-1-(4-methoxyphenyl)prop-2-en-1-one

Crystal data

C22H18O2	F(000) = 664
Mr = 314.38	Dx = 1.279 Mg m^−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 68 reflections
a = 35.232 (3) Å	θ = 4.9–20.3°
b = 7.4972 (5) Å	µ = 0.08 mm^−1
c = 6.2113 (3) Å	T = 296 K
β = 95.509 (6)°	Block, colourless
V = 1633.08 (18) Å^3	0.58 × 0.33 × 0.12 mm
Z = 4

Data collection

Bruker–Nonius KappaCCD diffractometer	Rint = 0.048
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 4.6°
φ and ω scans	h = −45→44
10464 measured reflections	k = −9→9
1843 independent reflections	l = −8→7
1408 reflections with I > 2σ(I)

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	H-atom parameters constrained
wR(F^2) = 0.145	w = 1/[σ^2(Fo^2) + (0.0548P)^2 + 1.2452P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1843 reflections	Δρmax = 0.33 e Å^−3
217 parameters	Δρmin = −0.18 e Å^−3
2 restraints

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
C1	0.23829 (13)	0.2512 (6)	−0.0009 (8)	0.0577 (12)
C2	0.20882 (14)	0.3430 (7)	−0.1137 (8)	0.0641 (12)
C3	0.17240 (12)	0.3410 (6)	−0.0436 (7)	0.0528 (11)
C4	0.16474 (11)	0.2475 (5)	0.1407 (6)	0.0391 (9)
C5	0.19513 (11)	0.1540 (6)	0.2472 (6)	0.0521 (10)
C6	0.23104 (12)	0.1558 (7)	0.1775 (8)	0.0620 (12)
C7	0.12628 (11)	0.2475 (5)	0.2187 (5)	0.0371 (8)
C8	0.09475 (11)	0.3218 (6)	0.0972 (6)	0.0484 (10)
C9	0.05906 (11)	0.3228 (6)	0.1705 (6)	0.0488 (10)
C10	0.05251 (12)	0.2507 (6)	0.3670 (7)	0.0467 (10)
C11	0.08329 (13)	0.1751 (7)	0.4881 (6)	0.0564 (11)
C12	0.11939 (12)	0.1749 (7)	0.4157 (6)	0.0533 (11)
C13	0.01328 (13)	0.2616 (6)	0.4404 (7)	0.0524 (10)
C14	0.00398 (12)	0.2131 (7)	0.6279 (7)	0.0579 (11)
C15	−0.03296 (12)	0.2508 (6)	0.7144 (7)	0.0554 (12)
C16	−0.07005 (12)	0.2548 (6)	0.5720 (6)	0.0449 (9)
C17	−0.07575 (11)	0.1720 (6)	0.3726 (6)	0.0504 (10)
C18	−0.11150 (12)	0.1684 (6)	0.2573 (6)	0.0516 (10)
C19	−0.14197 (11)	0.2517 (6)	0.3409 (6)	0.0462 (10)
C20	−0.13604 (12)	0.3400 (6)	0.5392 (6)	0.0492 (10)
C21	−0.10092 (11)	0.3397 (6)	0.6515 (6)	0.0475 (9)
C22	−0.18622 (15)	0.1552 (9)	0.0503 (8)	0.0773 (16)
O1	−0.03261 (11)	0.2721 (7)	0.9065 (6)	0.0865 (14)
O2	−0.17806 (9)	0.2576 (4)	0.2437 (5)	0.0611 (9)
H1	0.2627	0.2543	−0.0458	0.069*
H2	0.2133	0.4067	−0.2372	0.077*
H3	0.1528	0.4033	−0.1218	0.063*
H5	0.1910	0.0881	0.3697	0.063*
H6	0.2506	0.0913	0.2529	0.074*
H8	0.0979	0.3720	−0.0368	0.058*
H9	0.0388	0.3737	0.0847	0.059*
H11	0.0798	0.1232	0.6208	0.068*
H12	0.1396	0.1245	0.5026	0.064*
H13	−0.0060	0.3071	0.3428	0.063*
H14	0.0220	0.1491	0.7160	0.069*
H17	−0.0553	0.1177	0.3147	0.061*
H18	−0.1150	0.1103	0.1246	0.062*
H20	−0.1562	0.3992	0.5947	0.059*
H21	−0.0975	0.3975	0.7844	0.057*
H22A	−0.1729	0.2052	−0.0631	0.116*
H22B	−0.2132	0.1576	0.0081	0.116*
H22C	−0.1781	0.0342	0.0762	0.116*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.040 (2)	0.060 (3)	0.076 (3)	−0.007 (2)	0.020 (2)	−0.010 (2)
C2	0.064 (3)	0.061 (3)	0.072 (3)	−0.001 (2)	0.027 (2)	0.012 (2)
C3	0.046 (2)	0.057 (3)	0.058 (2)	0.0086 (19)	0.0124 (17)	0.016 (2)
C4	0.0400 (19)	0.034 (2)	0.043 (2)	−0.0050 (16)	0.0029 (15)	−0.0037 (16)
C5	0.045 (2)	0.060 (3)	0.050 (2)	−0.0012 (19)	0.0006 (17)	0.011 (2)
C6	0.046 (2)	0.063 (3)	0.075 (3)	0.003 (2)	−0.005 (2)	0.003 (2)
C7	0.0424 (19)	0.032 (2)	0.0366 (17)	−0.0028 (14)	0.0042 (14)	−0.0004 (14)
C8	0.046 (2)	0.056 (3)	0.044 (2)	−0.0024 (19)	0.0036 (16)	0.0070 (18)
C9	0.042 (2)	0.054 (3)	0.050 (2)	0.0039 (18)	0.0019 (17)	0.0007 (19)
C10	0.048 (2)	0.038 (2)	0.054 (2)	−0.0014 (16)	0.0087 (17)	−0.0060 (17)
C11	0.072 (3)	0.057 (3)	0.044 (2)	−0.001 (2)	0.022 (2)	0.0083 (19)
C12	0.055 (2)	0.058 (3)	0.047 (2)	0.008 (2)	0.0099 (18)	0.0084 (19)
C13	0.056 (2)	0.045 (2)	0.056 (3)	−0.0046 (19)	0.0044 (18)	−0.0018 (19)
C14	0.045 (2)	0.070 (3)	0.058 (3)	0.004 (2)	0.0040 (17)	0.001 (2)
C15	0.047 (2)	0.060 (3)	0.060 (3)	−0.007 (2)	0.012 (2)	−0.003 (2)
C16	0.045 (2)	0.042 (2)	0.051 (2)	−0.0058 (17)	0.0183 (16)	−0.0027 (17)
C17	0.043 (2)	0.056 (2)	0.055 (2)	−0.0051 (19)	0.0192 (17)	−0.014 (2)
C18	0.059 (2)	0.053 (3)	0.045 (2)	−0.007 (2)	0.0167 (18)	−0.0119 (19)
C19	0.043 (2)	0.047 (3)	0.050 (2)	−0.0037 (17)	0.0127 (17)	0.0053 (18)
C20	0.053 (2)	0.046 (2)	0.051 (2)	0.008 (2)	0.0223 (18)	−0.0010 (19)
C21	0.049 (2)	0.051 (2)	0.045 (2)	0.0006 (18)	0.0146 (16)	−0.0056 (18)
C22	0.070 (3)	0.100 (4)	0.059 (3)	−0.003 (3)	−0.008 (2)	−0.006 (3)
O1	0.064 (2)	0.141 (4)	0.054 (2)	0.001 (2)	0.0014 (15)	−0.019 (2)
O2	0.0494 (17)	0.070 (2)	0.064 (2)	0.0048 (15)	0.0055 (14)	0.0003 (16)

Geometric parameters (Å, º)

C1—C6	1.363 (7)	C19—O2	1.355 (5)
C1—C2	1.380 (7)	C19—C20	1.396 (6)
C2—C3	1.394 (6)	C20—C21	1.361 (6)
C3—C4	1.391 (6)	C22—O2	1.431 (6)
C4—C5	1.392 (6)	C1—H1	0.9300
C4—C7	1.482 (5)	C2—H2	0.9300
C5—C6	1.376 (6)	C3—H3	0.9300
C7—C12	1.382 (5)	C5—H5	0.9300
C7—C8	1.398 (5)	C6—H6	0.9300
C8—C9	1.378 (5)	C8—H8	0.9300
C9—C10	1.374 (6)	C9—H9	0.9300
C10—C11	1.381 (6)	C11—H11	0.9300
C10—C13	1.499 (6)	C12—H12	0.9300
C11—C12	1.389 (6)	C13—H13	0.9300
C13—C14	1.292 (6)	C14—H14	0.9300
C14—C15	1.482 (6)	C17—H17	0.9300
C15—O1	1.202 (5)	C18—H18	0.9300
C15—C16	1.506 (6)	C20—H20	0.9300
C16—C17	1.383 (6)	C21—H21	0.9300
C16—C21	1.391 (5)	C22—H22A	0.9600
C17—C18	1.388 (6)	C22—H22B	0.9600
C18—C19	1.385 (5)	C22—H22C	0.9600
C6—C1—C2	118.9 (4)	C2—C1—H1	120.5
C1—C2—C3	120.4 (4)	C1—C2—H2	119.8
C4—C3—C2	121.3 (4)	C3—C2—H2	119.8
C3—C4—C5	116.3 (4)	C4—C3—H3	119.3
C3—C4—C7	121.7 (3)	C2—C3—H3	119.3
C5—C4—C7	122.0 (3)	C6—C5—H5	118.9
C6—C5—C4	122.3 (4)	C4—C5—H5	118.9
C1—C6—C5	120.7 (4)	C1—C6—H6	119.7
C12—C7—C8	115.9 (3)	C5—C6—H6	119.7
C12—C7—C4	122.2 (3)	C9—C8—H8	119.1
C8—C7—C4	121.8 (3)	C7—C8—H8	119.1
C9—C8—C7	121.8 (4)	C10—C9—H9	119.1
C10—C9—C8	121.9 (4)	C8—C9—H9	119.1
C9—C10—C11	117.1 (4)	C10—C11—H11	119.3
C9—C10—C13	119.1 (4)	C12—C11—H11	119.3
C11—C10—C13	123.8 (4)	C7—C12—H12	119.0
C10—C11—C12	121.3 (4)	C11—C12—H12	119.0
C7—C12—C11	122.0 (4)	C14—C13—H13	117.3
C14—C13—C10	125.4 (4)	C10—C13—H13	117.3
C13—C14—C15	125.5 (4)	C13—C14—H14	117.3
O1—C15—C14	117.3 (4)	C15—C14—H14	117.3
O1—C15—C16	120.4 (4)	C16—C17—H17	119.4
C14—C15—C16	122.2 (4)	C18—C17—H17	119.4
C17—C16—C21	118.2 (4)	C19—C18—H18	120.2
C17—C16—C15	124.1 (4)	C17—C18—H18	120.2
C21—C16—C15	117.7 (4)	C21—C20—H20	119.9
C16—C17—C18	121.2 (4)	C19—C20—H20	119.9
C19—C18—C17	119.7 (4)	C20—C21—H21	119.3
O2—C19—C18	125.1 (4)	C16—C21—H21	119.3
O2—C19—C20	115.6 (3)	O2—C22—H22A	109.5
C18—C19—C20	119.2 (4)	O2—C22—H22B	109.5
C21—C20—C19	120.2 (3)	H22A—C22—H22B	109.5
C20—C21—C16	121.5 (4)	O2—C22—H22C	109.5
C19—O2—C22	117.5 (4)	H22A—C22—H22C	109.5
C6—C1—H1	120.5	H22B—C22—H22C	109.5