2-Benzoyl­oxy-5-methyl­benzo­phenone

In the crystal structure of the title compound, C₂₁H₁₆O₃, the mol­ecules are connected into centrosymmetric dimers by weak C—H...O intermolecular hydrogen bonds. The crystal packing is stabilized by C—H...π and π–π stacking interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.032
• wR factor = 0.088
• Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H81A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H82A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H83A
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H81B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H82B
PLAT166_ALERT_4_C S.U's Given on Coordinates for calc-flagged ....       H83B
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C14    -   C15     ..       5.54 su
PLAT701_ALERT_1_C Bond    Calc   0.996(16), Rep   0.966(16), Dev..       1.87 Sigma
              C14  -H14     1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 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
   0 ALERT type 3 Indicator that the structure quality may be low
   6 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 1990); program(s) used to refine structure: SHELXTL/PC; molecular graphics: SHELXTL/PC; software used to prepare material for publication: PLATON (Spek, 2004).

2-benzoyloxy-5-methylbenzophenone

Crystal data

C21H16O3	Z = 2
Mr = 316.34	F(000) = 332
Triclinic, P1	Dx = 1.294 Mg m^−3
Hall symbol: -P 1	Melting point: 351 K
a = 9.2068 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7961 (5) Å	Cell parameters from 5424 reflections
c = 10.1375 (6) Å	θ = 2.2–30.6°
α = 94.732 (4)°	µ = 0.09 mm^−1
β = 112.570 (5)°	T = 293 K
γ = 102.194 (4)°	Prism, colourless
V = 811.57 (9) Å^3	0.60 × 0.52 × 0.13 mm

Data collection

Kuma KM4CCD diffractometer	2563 reflections with I > 2σ(I)
Radiation source: CX-Mo12x0.4-S Seifert Mo tube	Rint = 0.036
Graphite monochromator	θmax = 25.0°, θmin = 3.7°
Detector resolution: 8.2356 pixels mm^-1	h = −10→10
ω scans	k = −11→11
9605 measured reflections	l = −12→12
2842 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0405P)^2 + 0.1213P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
2842 reflections	Δρmax = 0.12 e Å^−3
277 parameters	Δρmin = −0.12 e Å^−3
0 restraints	Extinction correction: SHELXTL/PC, FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (4)

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 on F^{2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F}2, conventional R-factors R are based on F, with F set to zero for negative F^{2. The observed criterion of F}2 > σ(F^{2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F}2 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	Occ. (<1)
O1	0.19341 (9)	0.06257 (9)	0.81458 (9)	0.0528 (2)
O2	0.05161 (10)	0.13717 (9)	0.61193 (9)	0.0533 (2)
O3	0.21050 (12)	0.37205 (10)	0.89921 (11)	0.0633 (3)
C1	0.34520 (13)	0.13631 (12)	0.82249 (12)	0.0447 (3)
C2	0.38858 (13)	0.28085 (12)	0.82327 (12)	0.0421 (3)
C3	0.54706 (14)	0.34233 (13)	0.84015 (12)	0.0455 (3)
H3	0.5800 (16)	0.4453 (15)	0.8431 (14)	0.055 (3)*
C4	0.66078 (14)	0.26461 (13)	0.85855 (12)	0.0482 (3)
C5	0.61143 (15)	0.12055 (14)	0.85525 (14)	0.0536 (3)
H5	0.6884 (19)	0.0625 (16)	0.8668 (15)	0.068 (4)*
C6	0.45466 (15)	0.05601 (13)	0.83607 (14)	0.0534 (3)
H6	0.4174 (17)	−0.0471 (17)	0.8329 (15)	0.065 (4)*
C7	0.27731 (13)	0.37411 (11)	0.81645 (13)	0.0448 (3)
C8	0.83276 (16)	0.33522 (17)	0.88365 (16)	0.0644 (4)
H81A	0.8450	0.4379	0.8822	0.049 (7)*	0.50
H82A	0.8583	0.2921	0.8061	0.063 (8)*	0.50
H83A	0.9086	0.3223	0.9792	0.047 (6)*	0.50
H81B	0.8962	0.2636	0.8962	0.074 (9)*	0.50
H82B	0.8830	0.4094	0.9723	0.098 (12)*	0.50
H83B	0.8326	0.3792	0.7991	0.076 (9)*	0.50
C9	0.05417 (13)	0.06507 (11)	0.70207 (12)	0.0422 (3)
C11	0.25473 (13)	0.47142 (11)	0.70942 (13)	0.0441 (3)
C12	0.27926 (15)	0.44326 (13)	0.58487 (13)	0.0504 (3)
H12	0.3149 (17)	0.3612 (16)	0.5682 (15)	0.063 (4)*
C13	0.24582 (18)	0.52963 (15)	0.48198 (16)	0.0620 (4)
H13	0.2621 (19)	0.5084 (17)	0.3947 (18)	0.075 (5)*
C14	0.18865 (17)	0.64452 (14)	0.50309 (17)	0.0633 (4)
H14	0.1618 (19)	0.7039 (17)	0.4264 (17)	0.075 (4)*
C15	0.16619 (17)	0.67450 (14)	0.62669 (18)	0.0642 (4)
H15	0.124 (2)	0.7529 (19)	0.6402 (18)	0.083 (5)*
C16	0.19808 (16)	0.58853 (13)	0.73024 (16)	0.0561 (3)
H16	0.1804 (17)	0.6057 (15)	0.8185 (16)	0.064 (4)*
C21	−0.08968 (13)	−0.03271 (11)	0.70640 (12)	0.0428 (3)
C22	−0.24127 (15)	−0.04899 (13)	0.59396 (14)	0.0496 (3)
H22	−0.2499 (16)	0.0038 (15)	0.5185 (15)	0.058 (4)*
C23	−0.37733 (16)	−0.14110 (14)	0.59284 (16)	0.0588 (3)
H23	−0.485 (2)	−0.1521 (16)	0.5129 (17)	0.073 (4)*
C24	−0.36363 (17)	−0.21613 (14)	0.70391 (17)	0.0623 (4)
H24	−0.458 (2)	−0.2792 (17)	0.7054 (17)	0.077 (4)*
C25	−0.21464 (17)	−0.20036 (15)	0.81624 (17)	0.0629 (4)
H25	−0.206 (2)	−0.2527 (18)	0.8952 (18)	0.080 (5)*
C26	−0.07720 (16)	−0.10926 (13)	0.81723 (15)	0.0534 (3)
H26	0.0291 (19)	−0.0967 (15)	0.8977 (16)	0.064 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0394 (4)	0.0507 (5)	0.0605 (5)	0.0041 (4)	0.0138 (4)	0.0229 (4)
O2	0.0503 (5)	0.0490 (5)	0.0529 (5)	0.0051 (4)	0.0157 (4)	0.0173 (4)
O3	0.0702 (6)	0.0622 (6)	0.0746 (6)	0.0198 (5)	0.0455 (5)	0.0183 (5)
C1	0.0377 (6)	0.0440 (6)	0.0455 (6)	0.0056 (5)	0.0118 (5)	0.0130 (5)
C2	0.0387 (6)	0.0420 (6)	0.0418 (6)	0.0081 (5)	0.0136 (5)	0.0096 (4)
C3	0.0413 (6)	0.0428 (6)	0.0472 (6)	0.0055 (5)	0.0156 (5)	0.0088 (5)
C4	0.0401 (6)	0.0580 (7)	0.0419 (6)	0.0104 (5)	0.0136 (5)	0.0084 (5)
C5	0.0459 (7)	0.0549 (7)	0.0560 (7)	0.0187 (6)	0.0139 (6)	0.0097 (6)
C6	0.0504 (7)	0.0421 (7)	0.0584 (7)	0.0123 (5)	0.0121 (6)	0.0117 (5)
C7	0.0393 (6)	0.0394 (6)	0.0509 (6)	0.0036 (5)	0.0178 (5)	0.0041 (5)
C8	0.0438 (7)	0.0804 (10)	0.0681 (9)	0.0132 (7)	0.0232 (6)	0.0169 (8)
C9	0.0425 (6)	0.0348 (5)	0.0460 (6)	0.0092 (4)	0.0155 (5)	0.0064 (5)
C11	0.0367 (6)	0.0363 (6)	0.0536 (7)	0.0063 (4)	0.0149 (5)	0.0061 (5)
C12	0.0518 (7)	0.0421 (6)	0.0557 (7)	0.0138 (5)	0.0195 (6)	0.0094 (5)
C13	0.0685 (9)	0.0580 (8)	0.0563 (8)	0.0169 (7)	0.0210 (7)	0.0166 (6)
C14	0.0600 (8)	0.0508 (8)	0.0693 (9)	0.0152 (6)	0.0138 (7)	0.0213 (7)
C15	0.0569 (8)	0.0420 (7)	0.0881 (11)	0.0191 (6)	0.0206 (7)	0.0130 (7)
C16	0.0522 (7)	0.0472 (7)	0.0682 (8)	0.0149 (5)	0.0242 (6)	0.0061 (6)
C21	0.0427 (6)	0.0350 (5)	0.0491 (6)	0.0081 (4)	0.0189 (5)	0.0049 (5)
C22	0.0465 (6)	0.0478 (7)	0.0509 (7)	0.0107 (5)	0.0175 (5)	0.0073 (5)
C23	0.0418 (7)	0.0573 (8)	0.0660 (8)	0.0052 (6)	0.0164 (6)	0.0010 (6)
C24	0.0509 (8)	0.0505 (7)	0.0832 (10)	0.0001 (6)	0.0331 (7)	0.0066 (7)
C25	0.0614 (8)	0.0545 (8)	0.0742 (9)	0.0067 (6)	0.0319 (7)	0.0222 (7)
C26	0.0484 (7)	0.0484 (7)	0.0588 (7)	0.0074 (5)	0.0188 (6)	0.0165 (6)

Geometric parameters (Å, º)

O1—C1	1.3997 (14)	C23—C24	1.375 (2)
O1—C9	1.3566 (15)	C24—C25	1.373 (2)
O2—C9	1.1965 (13)	C25—C26	1.3818 (18)
O3—C7	1.2151 (14)	C3—H3	0.985 (14)
C1—C2	1.3861 (16)	C5—H5	0.979 (15)
C1—C6	1.3783 (17)	C6—H6	0.989 (15)
C2—C3	1.3931 (16)	C8—H81A	0.99
C2—C7	1.4968 (16)	C8—H81B	0.99
C3—C4	1.3860 (17)	C8—H82A	0.99
C4—C5	1.3816 (18)	C8—H82B	0.99
C4—C8	1.4998 (17)	C8—H83A	0.99
C5—C6	1.3783 (18)	C8—H83B	0.99
C7—C11	1.4867 (16)	C12—H12	0.956 (15)
C9—C21	1.4796 (16)	C13—H13	0.966 (16)
C11—C12	1.3817 (17)	C14—H14	0.966 (16)
C11—C16	1.3893 (17)	C15—H15	0.955 (17)
C12—C13	1.3812 (18)	C16—H16	0.976 (15)
C13—C14	1.374 (2)	C22—H22	0.946 (14)
C14—C15	1.365 (2)	C23—H23	0.986 (16)
C15—C16	1.382 (2)	C24—H24	0.958 (17)
C21—C22	1.3883 (17)	C25—H25	0.972 (17)
C21—C26	1.3835 (17)	C26—H26	0.979 (15)
C22—C23	1.3760 (18)
C1—O1—C9	120.30 (8)	C4—C5—H5	119.9 (9)
O1—C1—C2	123.70 (10)	C6—C5—H5	118.8 (9)
O1—C1—C6	115.21 (10)	C1—C6—H6	118.1 (8)
C2—C1—C6	121.04 (11)	C5—C6—H6	122.1 (8)
C1—C2—C3	117.73 (10)	C4—C8—H81A	109.5
C1—C2—C7	123.14 (10)	C4—C8—H81B	109.5
C3—C2—C7	119.00 (10)	C4—C8—H82A	109.5
C2—C3—C4	122.27 (11)	C4—C8—H82B	109.5
C3—C4—C5	117.94 (11)	C4—C8—H83A	109.5
C3—C4—C8	120.98 (12)	C4—C8—H83B	109.5
C5—C4—C8	121.08 (11)	H81A—C8—H82A	109.5
C4—C5—C6	121.21 (11)	H81A—C8—H83A	109.5
C1—C6—C5	119.77 (11)	H81B—C8—H82B	109.5
O3—C7—C2	120.33 (10)	H81B—C8—H83B	109.5
O3—C7—C11	121.20 (11)	H82A—C8—H83A	109.5
C2—C7—C11	118.46 (10)	H82B—C8—H83B	109.5
O1—C9—O2	123.23 (10)	C11—C12—H12	119.6 (8)
O1—C9—C21	111.13 (9)	C13—C12—H12	120.1 (8)
O2—C9—C21	125.64 (10)	C12—C13—H13	119.6 (9)
C7—C11—C12	121.40 (10)	C14—C13—H13	120.1 (9)
C7—C11—C16	119.41 (11)	C13—C14—H14	119.2 (9)
C12—C11—C16	119.07 (11)	C15—C14—H14	120.8 (9)
C11—C12—C13	120.25 (12)	C14—C15—H15	120.0 (10)
C12—C13—C14	120.21 (14)	C16—C15—H15	119.5 (10)
C13—C14—C15	120.02 (13)	C11—C16—H16	117.6 (8)
C14—C15—C16	120.44 (13)	C15—C16—H16	122.4 (8)
C11—C16—C15	119.99 (14)	C21—C22—H22	119.4 (8)
C9—C21—C22	118.46 (10)	C23—C22—H22	120.5 (8)
C9—C21—C26	122.16 (10)	C22—C23—H23	119.9 (9)
C22—C21—C26	119.37 (11)	C24—C23—H23	120.1 (9)
C21—C22—C23	120.10 (12)	C23—C24—H24	120.8 (9)
C22—C23—C24	120.03 (13)	C25—C24—H24	118.7 (9)
C23—C24—C25	120.48 (12)	C24—C25—H25	120.2 (10)
C24—C25—C26	119.80 (13)	C26—C25—H25	120.0 (10)
C21—C26—C25	120.22 (12)	C21—C26—H26	119.6 (8)
C2—C3—H3	118.5 (8)	C25—C26—H26	120.1 (8)
C4—C3—H3	119.2 (8)
C9—O1—C1—C2	57.12 (15)	C2—C7—C11—C12	24.72 (16)
C9—O1—C1—C6	−125.59 (11)	O3—C7—C11—C16	18.96 (17)
C6—C1—C2—C3	−0.83 (17)	C16—C11—C12—C13	−0.80 (18)
O1—C1—C2—C3	176.30 (10)	C7—C11—C12—C13	175.18 (11)
C6—C1—C2—C7	−176.81 (11)	C11—C12—C13—C14	0.3 (2)
O1—C1—C2—C7	0.32 (17)	C12—C13—C14—C15	0.6 (2)
C1—C2—C3—C4	−1.23 (17)	C13—C14—C15—C16	−1.1 (2)
C7—C2—C3—C4	174.92 (10)	C14—C15—C16—C11	0.6 (2)
C2—C3—C4—C5	2.02 (18)	C12—C11—C16—C15	0.37 (18)
C2—C3—C4—C8	−177.01 (11)	C7—C11—C16—C15	−175.68 (11)
C3—C4—C5—C6	−0.78 (18)	O2—C9—C21—C26	−177.86 (12)
C8—C4—C5—C6	178.25 (12)	O1—C9—C21—C26	2.69 (15)
C2—C1—C6—C5	2.03 (19)	O2—C9—C21—C22	3.09 (17)
O1—C1—C6—C5	−175.33 (11)	O1—C9—C21—C22	−176.36 (10)
C4—C5—C6—C1	−1.20 (19)	C26—C21—C22—C23	−0.35 (18)
C1—C2—C7—O3	50.66 (16)	C9—C21—C22—C23	178.73 (11)
C3—C2—C7—O3	−125.27 (12)	C21—C22—C23—C24	0.7 (2)
C1—C2—C7—C11	−131.04 (11)	C22—C23—C24—C25	−0.2 (2)
C2—C7—C11—C16	−159.32 (11)	C23—C24—C25—C26	−0.5 (2)
C3—C2—C7—C11	53.02 (14)	C24—C25—C26—C21	0.8 (2)
C1—O1—C9—O2	−6.05 (17)	C22—C21—C26—C25	−0.38 (19)
C1—O1—C9—C21	173.42 (9)	C9—C21—C26—C25	−179.43 (12)
O3—C7—C11—C12	−157.00 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···Cg1^i	0.979 (15)	2.782 (17)	3.5966 (16)	141.2 (11)
C24—H24···Cg2^ii	0.958 (17)	2.774 (19)	3.6848 (17)	158.7 (13)
C25—H25···O3^iii	0.972 (17)	2.483 (17)	3.4487 (17)	172.4 (13)

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