1,5-Bis(4-methoxy­phen­yl)-3-phenyl­pentane-1,5-dione

In the title mol­ecule, C₂₅H₂₄O₄, the central phenyl ring makes dihedral angles of 85.92 (12) and 78.21 (13)° with the two outer benzene rings. The crystal packing is stabilized by van der Waals forces.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.164
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         44 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C5
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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

   1 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: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); 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-methoxyphenyl)-3-phenylpentane-1,5-dione

Crystal data

C25H24O4	F(000) = 824
Mr = 388.44	Dx = 1.261 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.673 (3) Å	Cell parameters from 1363 reflections
b = 24.014 (14) Å	θ = 2.7–25.3°
c = 15.059 (9) Å	µ = 0.09 mm^−1
β = 94.028 (9)°	T = 298 K
V = 2046 (2) Å^3	Block, colourless
Z = 4	0.35 × 0.17 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3607 independent reflections
Radiation source: fine-focus sealed tube	1599 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.971, Tmax = 0.987	k = −28→17
10442 measured reflections	l = −15→17

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + 0.4792P] where P = (Fo^2 + 2Fc^2)/3
3607 reflections	(Δ/σ)max < 0.001
262 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.16 e Å^−3

Special details

Experimental. C₂₅H₂₄O₄: C 77.30, H 6.22%; Found: C 77.25, H 6.26%.

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
O1	0.3122 (5)	0.51834 (10)	0.6729 (2)	0.0943 (10)
O2	1.0007 (5)	0.70796 (11)	0.56021 (19)	0.0971 (9)
O3	0.1996 (4)	0.31701 (10)	0.6882 (2)	0.0919 (9)
O4	0.7015 (4)	0.08606 (11)	0.62703 (17)	0.0810 (8)
C1	0.5051 (6)	0.51459 (15)	0.6419 (2)	0.0607 (10)
C2	0.6324 (6)	0.56522 (14)	0.6179 (2)	0.0542 (9)
C3	0.8330 (6)	0.56456 (15)	0.5715 (2)	0.0640 (10)
H3	0.8916	0.5306	0.5531	0.077*
C4	0.9478 (6)	0.61242 (16)	0.5519 (3)	0.0759 (11)
H4	1.0811	0.6108	0.5194	0.091*
C5	0.8669 (7)	0.66328 (16)	0.5801 (2)	0.0657 (10)
C6	0.6681 (7)	0.66546 (15)	0.6250 (2)	0.0739 (11)
H6	0.6106	0.6996	0.6432	0.089*
C7	0.5515 (7)	0.61684 (16)	0.6435 (2)	0.0713 (11)
H7	0.4148	0.6188	0.6740	0.086*
C8	0.9229 (9)	0.76179 (16)	0.5877 (3)	0.1130 (17)
H8A	0.7819	0.7721	0.5526	0.169*
H8B	1.0443	0.7888	0.5796	0.169*
H8C	0.8905	0.7605	0.6494	0.169*
C9	0.3897 (6)	0.30720 (14)	0.6576 (2)	0.0605 (10)
C10	0.4713 (6)	0.24921 (14)	0.6490 (2)	0.0529 (9)
C11	0.6742 (6)	0.23511 (15)	0.6083 (2)	0.0657 (10)
H11	0.7655	0.2630	0.5851	0.079*
C12	0.7423 (6)	0.18067 (15)	0.6017 (3)	0.0710 (11)
H12	0.8784	0.1720	0.5735	0.085*
C13	0.6126 (6)	0.13864 (15)	0.6362 (2)	0.0587 (9)
C14	0.4119 (6)	0.15118 (15)	0.6764 (2)	0.0666 (10)
H14	0.3229	0.1230	0.6999	0.080*
C15	0.3409 (6)	0.20603 (16)	0.6822 (2)	0.0670 (10)
H15	0.2022	0.2142	0.7090	0.080*
C16	0.5751 (7)	0.04041 (15)	0.6602 (3)	0.0865 (13)
H16A	0.5590	0.0454	0.7227	0.130*
H16B	0.6595	0.0065	0.6508	0.130*
H16C	0.4213	0.0384	0.6294	0.130*
C17	0.6115 (5)	0.45818 (13)	0.6266 (2)	0.0588 (9)
H17A	0.7757	0.4586	0.6493	0.071*
H17B	0.6078	0.4514	0.5630	0.071*
C18	0.4852 (5)	0.40994 (12)	0.6707 (2)	0.0522 (8)
H18	0.3147	0.4163	0.6609	0.063*
C19	0.5403 (6)	0.35451 (13)	0.6282 (2)	0.0602 (9)
H19A	0.5175	0.3582	0.5640	0.072*
H19B	0.7052	0.3455	0.6427	0.072*
C20	0.5458 (6)	0.40946 (12)	0.7707 (2)	0.0489 (8)
C21	0.7603 (6)	0.38912 (13)	0.8078 (3)	0.0627 (10)
H21	0.8706	0.3749	0.7710	0.075*
C22	0.8103 (7)	0.38988 (15)	0.8986 (3)	0.0759 (11)
H22	0.9542	0.3760	0.9225	0.091*
C23	0.6519 (8)	0.41068 (16)	0.9540 (3)	0.0795 (12)
H23	0.6870	0.4109	1.0153	0.095*
C24	0.4406 (8)	0.43131 (15)	0.9186 (3)	0.0775 (11)
H24	0.3326	0.4460	0.9560	0.093*
C25	0.3873 (6)	0.43048 (13)	0.8282 (2)	0.0593 (9)
H25	0.2425	0.4442	0.8052	0.071*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0771 (18)	0.0735 (19)	0.137 (3)	0.0244 (14)	0.0385 (18)	0.0336 (16)
O2	0.121 (2)	0.0580 (19)	0.115 (3)	−0.0088 (17)	0.0283 (19)	0.0064 (16)
O3	0.0664 (16)	0.0700 (18)	0.144 (3)	−0.0042 (13)	0.0388 (17)	−0.0295 (16)
O4	0.0969 (19)	0.0560 (17)	0.093 (2)	0.0052 (14)	0.0299 (15)	0.0013 (14)
C1	0.061 (2)	0.062 (3)	0.060 (2)	0.017 (2)	0.0100 (18)	0.0119 (18)
C2	0.062 (2)	0.051 (2)	0.050 (2)	0.0088 (18)	0.0086 (17)	0.0071 (16)
C3	0.067 (2)	0.054 (2)	0.073 (3)	0.0090 (19)	0.019 (2)	−0.0008 (19)
C4	0.076 (3)	0.063 (3)	0.092 (3)	0.004 (2)	0.029 (2)	0.004 (2)
C5	0.085 (3)	0.053 (3)	0.060 (3)	0.001 (2)	0.013 (2)	0.0066 (19)
C6	0.106 (3)	0.054 (3)	0.064 (3)	0.013 (2)	0.020 (2)	0.0003 (19)
C7	0.089 (3)	0.066 (3)	0.062 (3)	0.018 (2)	0.027 (2)	0.0040 (19)
C8	0.185 (5)	0.055 (3)	0.101 (4)	−0.012 (3)	0.024 (3)	0.001 (2)
C9	0.056 (2)	0.058 (2)	0.068 (3)	−0.0042 (18)	0.0086 (18)	−0.0182 (18)
C10	0.054 (2)	0.049 (2)	0.056 (2)	−0.0064 (16)	0.0074 (17)	−0.0121 (16)
C11	0.066 (2)	0.055 (3)	0.080 (3)	−0.0082 (18)	0.024 (2)	−0.0029 (19)
C12	0.066 (2)	0.054 (3)	0.095 (3)	−0.001 (2)	0.030 (2)	−0.004 (2)
C13	0.066 (2)	0.052 (2)	0.058 (2)	0.0026 (19)	0.0108 (18)	−0.0075 (18)
C14	0.073 (2)	0.057 (3)	0.072 (3)	−0.0154 (19)	0.021 (2)	−0.0052 (19)
C15	0.061 (2)	0.068 (3)	0.075 (3)	−0.010 (2)	0.0237 (19)	−0.016 (2)
C16	0.117 (3)	0.054 (3)	0.088 (3)	−0.003 (2)	0.004 (3)	0.019 (2)
C17	0.069 (2)	0.054 (2)	0.054 (2)	0.0058 (18)	0.0062 (17)	0.0033 (17)
C18	0.056 (2)	0.049 (2)	0.052 (2)	0.0032 (16)	0.0050 (16)	−0.0031 (16)
C19	0.069 (2)	0.054 (2)	0.059 (2)	−0.0049 (18)	0.0097 (18)	−0.0083 (17)
C20	0.054 (2)	0.0416 (19)	0.051 (2)	−0.0040 (16)	0.0068 (16)	−0.0026 (15)
C21	0.056 (2)	0.057 (2)	0.075 (3)	−0.0008 (17)	−0.0019 (19)	0.0025 (18)
C22	0.074 (3)	0.079 (3)	0.071 (3)	−0.014 (2)	−0.017 (2)	0.018 (2)
C23	0.101 (3)	0.084 (3)	0.053 (3)	−0.027 (3)	−0.002 (3)	0.010 (2)
C24	0.091 (3)	0.079 (3)	0.064 (3)	−0.010 (2)	0.019 (2)	−0.006 (2)
C25	0.062 (2)	0.059 (2)	0.057 (3)	0.0011 (17)	0.0059 (18)	−0.0018 (18)

Geometric parameters (Å, º)

O1—C1	1.223 (4)	C12—H12	0.9300
O2—C5	1.360 (4)	C13—C14	1.361 (4)
O2—C8	1.436 (4)	C14—C15	1.382 (4)
O3—C9	1.225 (4)	C14—H14	0.9300
O4—C13	1.370 (4)	C15—H15	0.9300
O4—C16	1.420 (4)	C16—H16A	0.9600
C1—C2	1.472 (4)	C16—H16B	0.9600
C1—C17	1.507 (4)	C16—H16C	0.9600
C2—C3	1.377 (4)	C17—C18	1.537 (4)
C2—C7	1.386 (4)	C17—H17A	0.9700
C3—C4	1.364 (4)	C17—H17B	0.9700
C3—H3	0.9300	C18—C19	1.520 (4)
C4—C5	1.382 (5)	C18—C20	1.521 (4)
C4—H4	0.9300	C18—H18	0.9800
C5—C6	1.356 (5)	C19—H19A	0.9700
C6—C7	1.380 (5)	C19—H19B	0.9700
C6—H6	0.9300	C20—C25	1.386 (4)
C7—H7	0.9300	C20—C21	1.391 (4)
C8—H8A	0.9600	C21—C22	1.378 (5)
C8—H8B	0.9600	C21—H21	0.9300
C8—H8C	0.9600	C22—C23	1.363 (5)
C9—C10	1.476 (4)	C22—H22	0.9300
C9—C19	1.507 (4)	C23—C24	1.370 (5)
C10—C11	1.384 (4)	C23—H23	0.9300
C10—C15	1.387 (4)	C24—C25	1.374 (5)
C11—C12	1.369 (4)	C24—H24	0.9300
C11—H11	0.9300	C25—H25	0.9300
C12—C13	1.372 (4)
C5—O2—C8	117.3 (3)	C15—C14—H14	120.1
C13—O4—C16	118.5 (3)	C14—C15—C10	121.6 (3)
O1—C1—C2	120.0 (3)	C14—C15—H15	119.2
O1—C1—C17	120.2 (3)	C10—C15—H15	119.2
C2—C1—C17	119.8 (3)	O4—C16—H16A	109.5
C3—C2—C7	116.9 (3)	O4—C16—H16B	109.5
C3—C2—C1	123.5 (3)	H16A—C16—H16B	109.5
C7—C2—C1	119.6 (3)	O4—C16—H16C	109.5
C4—C3—C2	121.6 (3)	H16A—C16—H16C	109.5
C4—C3—H3	119.2	H16B—C16—H16C	109.5
C2—C3—H3	119.2	C1—C17—C18	114.1 (3)
C3—C4—C5	120.3 (3)	C1—C17—H17A	108.7
C3—C4—H4	119.9	C18—C17—H17A	108.7
C5—C4—H4	119.9	C1—C17—H17B	108.7
C6—C5—O2	125.2 (4)	C18—C17—H17B	108.7
C6—C5—C4	119.5 (4)	H17A—C17—H17B	107.6
O2—C5—C4	115.3 (4)	C19—C18—C20	111.9 (3)
C5—C6—C7	119.7 (4)	C19—C18—C17	111.2 (3)
C5—C6—H6	120.2	C20—C18—C17	110.7 (3)
C7—C6—H6	120.2	C19—C18—H18	107.6
C6—C7—C2	121.9 (3)	C20—C18—H18	107.6
C6—C7—H7	119.1	C17—C18—H18	107.6
C2—C7—H7	119.1	C9—C19—C18	113.5 (3)
O2—C8—H8A	109.5	C9—C19—H19A	108.9
O2—C8—H8B	109.5	C18—C19—H19A	108.9
H8A—C8—H8B	109.5	C9—C19—H19B	108.9
O2—C8—H8C	109.5	C18—C19—H19B	108.9
H8A—C8—H8C	109.5	H19A—C19—H19B	107.7
H8B—C8—H8C	109.5	C25—C20—C21	117.7 (3)
O3—C9—C10	120.3 (3)	C25—C20—C18	120.3 (3)
O3—C9—C19	119.9 (3)	C21—C20—C18	122.1 (3)
C10—C9—C19	119.8 (3)	C22—C21—C20	120.5 (4)
C11—C10—C15	117.3 (3)	C22—C21—H21	119.7
C11—C10—C9	123.1 (3)	C20—C21—H21	119.7
C15—C10—C9	119.7 (3)	C23—C22—C21	120.9 (4)
C12—C11—C10	120.9 (3)	C23—C22—H22	119.5
C12—C11—H11	119.5	C21—C22—H22	119.5
C10—C11—H11	119.5	C22—C23—C24	119.4 (4)
C11—C12—C13	120.9 (3)	C22—C23—H23	120.3
C11—C12—H12	119.6	C24—C23—H23	120.3
C13—C12—H12	119.6	C23—C24—C25	120.4 (4)
C14—C13—O4	125.0 (3)	C23—C24—H24	119.8
C14—C13—C12	119.6 (3)	C25—C24—H24	119.8
O4—C13—C12	115.4 (3)	C24—C25—C20	121.1 (3)
C13—C14—C15	119.7 (3)	C24—C25—H25	119.4
C13—C14—H14	120.1	C20—C25—H25	119.4