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

The title compound, C₂₅H₂₄O₂, has been synthesized by the reaction of benzaldehyde with 4-methyl­acetophenone and NaOH. The bond lengths and angles show normal values. The crystal packing exhibits no significantly short inter­molecular contacts.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.042
• wR factor = 0.126
• Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C12

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           25.01
           From the CIF: _reflns_number_total               1998
           Count of symmetry unique reflns         2000
           Completeness (_total/calc)             99.90%
           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
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion

---

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-methylphenyl)-3-phenylpentane-1,5-dione

Crystal data

C25H24O2	Dx = 1.222 Mg m^−3
Mr = 356.44	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1310 reflections
a = 5.715 (3) Å	θ = 2.6–18.4°
b = 15.848 (8) Å	µ = 0.08 mm^−1
c = 21.386 (11) Å	T = 298 K
V = 1936.8 (17) Å^3	Block, colourless
Z = 4	0.23 × 0.18 × 0.15 mm
F(000) = 760

Data collection

Bruker SMART CCD area-detector diffractometer	1998 independent reflections
Radiation source: fine-focus sealed tube	1166 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.983, Tmax = 0.989	k = −16→18
10270 measured reflections	l = −23→25

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.056P)^2 + 0.0975P] where P = (Fo^2 + 2Fc^2)/3
1998 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.15 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

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
O1	0.4991 (6)	0.9862 (2)	0.85816 (13)	0.0785 (11)
O2	0.2530 (6)	0.9483 (2)	0.64203 (15)	0.0801 (11)
C1	0.6831 (9)	0.9493 (2)	0.84979 (18)	0.0490 (11)
C2	0.7657 (8)	0.9305 (2)	0.78425 (16)	0.0466 (10)
H2A	0.7895	0.8701	0.7801	0.056*
H2B	0.9155	0.9578	0.7776	0.056*
C3	0.5952 (8)	0.9597 (2)	0.73361 (17)	0.0459 (11)
H3	0.4370	0.9455	0.7478	0.055*
C4	0.6371 (8)	0.9126 (2)	0.67272 (17)	0.0514 (11)
H4A	0.7802	0.9335	0.6539	0.062*
H4B	0.6602	0.8533	0.6821	0.062*
C5	0.4422 (8)	0.9205 (2)	0.62593 (19)	0.0489 (11)
C6	0.8229 (8)	0.9198 (2)	0.90347 (18)	0.0446 (10)
C7	1.0350 (8)	0.8798 (2)	0.89657 (19)	0.0523 (11)
H7	1.0968	0.8722	0.8567	0.063*
C8	1.1582 (8)	0.8507 (2)	0.94808 (19)	0.0583 (12)
H8	1.3003	0.8232	0.9422	0.070*
C9	1.0737 (9)	0.8617 (2)	1.00757 (19)	0.0543 (12)
C10	0.8609 (9)	0.9023 (3)	1.0146 (2)	0.0600 (13)
H10	0.8008	0.9107	1.0546	0.072*
C11	0.7372 (9)	0.9304 (2)	0.96384 (18)	0.0557 (12)
H11	0.5938	0.9570	0.9698	0.067*
C12	1.2100 (10)	0.8322 (3)	1.0635 (2)	0.0800 (16)
H12A	1.3517	0.8054	1.0499	0.120*
H12B	1.1177	0.7927	1.0870	0.120*
H12C	1.2479	0.8797	1.0895	0.120*
C13	0.4824 (8)	0.8939 (2)	0.56068 (19)	0.0479 (11)
C14	0.6820 (8)	0.8522 (2)	0.54201 (18)	0.0517 (11)
H14	0.7978	0.8403	0.5713	0.062*
C15	0.7130 (9)	0.8278 (2)	0.4808 (2)	0.0561 (12)
H15	0.8471	0.7981	0.4698	0.067*
C16	0.5495 (9)	0.8465 (3)	0.43559 (19)	0.0573 (12)
C17	0.3515 (9)	0.8888 (3)	0.4542 (2)	0.0639 (13)
H17	0.2382	0.9021	0.4246	0.077*
C18	0.3162 (8)	0.9119 (2)	0.5155 (2)	0.0562 (12)
H18	0.1794	0.9400	0.5267	0.067*
C19	0.5889 (11)	0.8200 (3)	0.3687 (2)	0.0881 (17)
H19A	0.5825	0.7596	0.3658	0.132*
H19B	0.7398	0.8394	0.3551	0.132*
H19C	0.4697	0.8442	0.3426	0.132*
C20	0.6046 (7)	1.0547 (2)	0.72477 (17)	0.0410 (10)
C21	0.7969 (8)	1.0938 (2)	0.69837 (18)	0.0492 (11)
H21	0.9230	1.0614	0.6849	0.059*
C22	0.8040 (9)	1.1806 (3)	0.6917 (2)	0.0600 (13)
H22	0.9332	1.2058	0.6730	0.072*
C23	0.6258 (9)	1.2290 (3)	0.7121 (2)	0.0627 (14)
H23	0.6333	1.2874	0.7083	0.075*
C24	0.4322 (9)	1.1913 (3)	0.73857 (19)	0.0584 (13)
H24	0.3077	1.2243	0.7523	0.070*
C25	0.4231 (8)	1.1056 (3)	0.74469 (17)	0.0505 (11)
H25	0.2917	1.0809	0.7627	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.072 (3)	0.102 (3)	0.061 (2)	0.036 (2)	0.0187 (18)	0.0166 (17)
O2	0.052 (2)	0.109 (3)	0.080 (2)	0.015 (2)	−0.0037 (19)	−0.0328 (19)
C1	0.055 (3)	0.043 (2)	0.049 (3)	0.007 (2)	0.010 (2)	0.0037 (19)
C2	0.050 (3)	0.046 (2)	0.044 (2)	0.003 (2)	0.004 (2)	−0.0022 (18)
C3	0.051 (3)	0.040 (2)	0.047 (2)	0.007 (2)	0.001 (2)	−0.0011 (17)
C4	0.053 (3)	0.049 (2)	0.051 (2)	0.007 (2)	−0.005 (2)	−0.0049 (19)
C5	0.043 (3)	0.045 (2)	0.059 (3)	0.002 (2)	−0.003 (2)	−0.0082 (19)
C6	0.048 (3)	0.041 (2)	0.045 (2)	0.002 (2)	0.003 (2)	−0.0009 (18)
C7	0.056 (3)	0.054 (3)	0.047 (3)	0.005 (2)	0.005 (2)	−0.0042 (19)
C8	0.055 (3)	0.063 (3)	0.057 (3)	0.008 (3)	−0.002 (2)	−0.002 (2)
C9	0.058 (3)	0.053 (3)	0.052 (3)	0.000 (3)	−0.006 (2)	−0.002 (2)
C10	0.075 (4)	0.062 (3)	0.043 (3)	0.000 (3)	0.007 (3)	−0.003 (2)
C11	0.057 (3)	0.059 (3)	0.051 (3)	0.007 (3)	0.012 (2)	−0.006 (2)
C12	0.085 (4)	0.093 (4)	0.062 (3)	0.009 (3)	−0.017 (3)	0.004 (3)
C13	0.048 (3)	0.041 (2)	0.055 (3)	−0.001 (2)	−0.008 (2)	0.0042 (19)
C14	0.052 (3)	0.053 (2)	0.050 (3)	0.007 (2)	−0.009 (2)	−0.001 (2)
C15	0.056 (3)	0.059 (3)	0.053 (3)	0.005 (3)	−0.005 (3)	−0.001 (2)
C16	0.066 (3)	0.057 (3)	0.049 (3)	−0.011 (3)	−0.004 (3)	0.009 (2)
C17	0.063 (4)	0.071 (3)	0.058 (3)	−0.007 (3)	−0.018 (3)	0.013 (2)
C18	0.043 (3)	0.054 (3)	0.071 (3)	0.007 (2)	−0.010 (3)	0.004 (2)
C19	0.103 (5)	0.108 (4)	0.053 (3)	−0.023 (4)	−0.006 (3)	0.003 (3)
C20	0.044 (3)	0.041 (2)	0.038 (2)	0.002 (2)	0.002 (2)	0.0005 (17)
C21	0.047 (3)	0.048 (3)	0.052 (3)	0.003 (2)	0.007 (2)	0.0007 (18)
C22	0.060 (3)	0.057 (3)	0.063 (3)	−0.006 (3)	0.013 (3)	0.004 (2)
C23	0.079 (4)	0.044 (3)	0.065 (3)	−0.003 (3)	0.010 (3)	0.006 (2)
C24	0.064 (4)	0.047 (3)	0.064 (3)	0.010 (3)	0.010 (3)	−0.002 (2)
C25	0.047 (3)	0.045 (2)	0.059 (3)	0.004 (2)	0.006 (2)	0.0007 (19)

Geometric parameters (Å, º)

O1—C1	1.217 (5)	C12—H12C	0.9600
O2—C5	1.217 (5)	C13—C14	1.378 (5)
C1—C6	1.475 (6)	C13—C18	1.385 (6)
C1—C2	1.509 (5)	C14—C15	1.376 (5)
C2—C3	1.529 (5)	C14—H14	0.9300
C2—H2A	0.9700	C15—C16	1.377 (6)
C2—H2B	0.9700	C15—H15	0.9300
C3—C20	1.519 (5)	C16—C17	1.374 (6)
C3—C4	1.520 (5)	C16—C19	1.508 (6)
C3—H3	0.9800	C17—C18	1.376 (6)
C4—C5	1.503 (6)	C17—H17	0.9300
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—H19A	0.9600
C5—C13	1.476 (5)	C19—H19B	0.9600
C6—C7	1.376 (6)	C19—H19C	0.9600
C6—C11	1.391 (5)	C20—C25	1.381 (5)
C7—C8	1.387 (5)	C20—C21	1.383 (5)
C7—H7	0.9300	C21—C22	1.383 (5)
C8—C9	1.372 (5)	C21—H21	0.9300
C8—H8	0.9300	C22—C23	1.348 (6)
C9—C10	1.384 (6)	C22—H22	0.9300
C9—C12	1.503 (6)	C23—C24	1.380 (6)
C10—C11	1.370 (6)	C23—H23	0.9300
C10—H10	0.9300	C24—C25	1.366 (5)
C11—H11	0.9300	C24—H24	0.9300
C12—H12A	0.9600	C25—H25	0.9300
C12—H12B	0.9600
O1—C1—C6	120.4 (4)	C9—C12—H12C	109.5
O1—C1—C2	120.2 (4)	H12A—C12—H12C	109.5
C6—C1—C2	119.4 (4)	H12B—C12—H12C	109.5
C1—C2—C3	113.5 (3)	C14—C13—C18	117.7 (4)
C1—C2—H2A	108.9	C14—C13—C5	122.7 (4)
C3—C2—H2A	108.9	C18—C13—C5	119.6 (4)
C1—C2—H2B	108.9	C15—C14—C13	121.1 (4)
C3—C2—H2B	108.9	C15—C14—H14	119.4
H2A—C2—H2B	107.7	C13—C14—H14	119.4
C20—C3—C4	112.0 (3)	C14—C15—C16	121.4 (4)
C20—C3—C2	111.5 (3)	C14—C15—H15	119.3
C4—C3—C2	111.0 (3)	C16—C15—H15	119.3
C20—C3—H3	107.4	C17—C16—C15	117.4 (4)
C4—C3—H3	107.4	C17—C16—C19	122.3 (5)
C2—C3—H3	107.4	C15—C16—C19	120.3 (5)
C5—C4—C3	114.4 (4)	C16—C17—C18	121.8 (4)
C5—C4—H4A	108.7	C16—C17—H17	119.1
C3—C4—H4A	108.7	C18—C17—H17	119.1
C5—C4—H4B	108.7	C17—C18—C13	120.6 (4)
C3—C4—H4B	108.7	C17—C18—H18	119.7
H4A—C4—H4B	107.6	C13—C18—H18	119.7
O2—C5—C13	120.6 (4)	C16—C19—H19A	109.5
O2—C5—C4	120.0 (4)	C16—C19—H19B	109.5
C13—C5—C4	119.4 (4)	H19A—C19—H19B	109.5
C7—C6—C11	117.8 (4)	C16—C19—H19C	109.5
C7—C6—C1	122.7 (4)	H19A—C19—H19C	109.5
C11—C6—C1	119.6 (4)	H19B—C19—H19C	109.5
C6—C7—C8	121.0 (4)	C25—C20—C21	117.5 (4)
C6—C7—H7	119.5	C25—C20—C3	120.9 (4)
C8—C7—H7	119.5	C21—C20—C3	121.6 (4)
C9—C8—C7	121.0 (4)	C20—C21—C22	120.7 (4)
C9—C8—H8	119.5	C20—C21—H21	119.6
C7—C8—H8	119.5	C22—C21—H21	119.6
C8—C9—C10	118.0 (4)	C23—C22—C21	120.7 (5)
C8—C9—C12	121.1 (5)	C23—C22—H22	119.6
C10—C9—C12	120.9 (4)	C21—C22—H22	119.6
C11—C10—C9	121.2 (4)	C22—C23—C24	119.5 (4)
C11—C10—H10	119.4	C22—C23—H23	120.3
C9—C10—H10	119.4	C24—C23—H23	120.3
C10—C11—C6	121.0 (4)	C25—C24—C23	120.1 (4)
C10—C11—H11	119.5	C25—C24—H24	120.0
C6—C11—H11	119.5	C23—C24—H24	120.0
C9—C12—H12A	109.5	C24—C25—C20	121.5 (4)
C9—C12—H12B	109.5	C24—C25—H25	119.2
H12A—C12—H12B	109.5	C20—C25—H25	119.2