A new look at two polymorphic crystal structures of di­benzoyl­methane: relationship between the crystal packing and the hydrogen atom position revealed by quantum chemistry and quantum crystallography methods

Chalcones, including di­benzoyl­methane, are an important subgroup of natural polyphenolic compounds that exhibit a wide spectrum of pharmacological and industrial applications. Di­benzoyl­methane was isolated from Hottonia palustris L. (Primulaceae). The compound was crystallized in two polymorphic forms: in monoclinic space group P2₁/c and orthorhombic space group Pbca. Crystal structures of the polymorphs were solved and refined against diffraction data measured at 100 and 293 K. In both crystal structures, the chalcone occurs in its keto–enol tautomeric form with the hydroxyl H atom mutually bound by two oxygen atoms rather than covalently attached to a particular oxygen atom. To explain this phenomenon in more detail, density functional theory and quantum theory of atoms in molecules based quantum chemistry calculations were applied. Additionally, high-resolution experimental data of very high quality measured for the monoclinic and orthorhombic crystals at 100 K allowed the engagement of the quantum crystallography method, based on Hirshfeld atom refinement, to determine the position of each individual H atom. It is suggested that the presence of the particular tautomeric form of di­benzoyl­methane with a centred H atom position results from the π-stacking interaction between the phenyl ring and the malondi­aldehyde quasi-ring causes delocalization of the electron density in the latter.

Computing details

Data collection: CrysAlis PRO (Agilent Technologies, 2011) for exp_3401, exp_3318, exp_3421, exp_3402. Cell refinement: CrysAlis PRO (Agilent Technologies, 2011) for exp_3401, exp_3318, exp_3421, exp_3402. Data reduction: CrysAlis PRO (Agilent Technologies, 2011) for exp_3401, exp_3318, exp_3421, exp_3402. Program(s) used to solve structure: SHELXD2016(Sheldrick, 2016) for exp_3401, exp_3318, exp_3421, exp_3402. Program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2016) for exp_3401, exp_3318, exp_3421, exp_3402. Molecular graphics: OLEX2 (Dolomanov et al., 2009) for exp_3401, exp_3318, exp_3421, exp_3402. Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) for exp_3401, exp_3318, exp_3421, exp_3402.

(exp_3401)

Crystal data

C15H12O2	F(000) = 472
Mr = 224.25	Dx = 1.281 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.4919 (2) Å	Cell parameters from 5859 reflections
b = 11.8600 (2) Å	θ = 3.7–76.6°
c = 8.06206 (15) Å	µ = 0.68 mm^−1
β = 103.2761 (19)°	T = 293 K
V = 1162.50 (4) Å^3	Needle, yellow
Z = 4	0.52 × 0.12 × 0.09 mm

Data collection

SuperNova, Dual, Mo at zero, Atlas diffractometer	2429 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source	2035 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.039
Detector resolution: 10.4052 pixels mm^-1	θmax = 76.6°, θmin = 5.2°
ω scans	h = −15→15
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→14
Tmin = 0.659, Tmax = 1.000	l = −10→8
11937 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.068	w = 1/[σ^2(Fo^2) + (0.1481P)^2 + 0.0887P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.205	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.19 e Å^−3
2429 reflections	Δρmin = −0.24 e Å^−3
196 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
10 restraints	Extinction coefficient: 0.033 (6)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.58395 (11)	0.90492 (10)	0.3528 (2)	0.0776 (5)
H1	0.673 (3)	0.908 (3)	0.306 (4)	0.141 (11)*
O2	0.76054 (11)	0.86933 (10)	0.27540 (19)	0.0731 (4)
C1	0.46517 (11)	0.76051 (12)	0.40105 (17)	0.0497 (4)
C2	0.39511 (14)	0.84138 (15)	0.4418 (2)	0.0639 (5)
H2	0.413966	0.917256	0.442443	0.077*
C3	0.29734 (15)	0.80973 (18)	0.4816 (3)	0.0753 (6)
H3	0.250931	0.864442	0.509017	0.090*
C4	0.26858 (15)	0.69835 (19)	0.4808 (2)	0.0731 (5)
H4	0.202767	0.677515	0.507524	0.088*
C5	0.33713 (15)	0.61723 (16)	0.4404 (3)	0.0716 (5)
H5	0.317469	0.541560	0.439458	0.086*
C6	0.43504 (13)	0.64794 (14)	0.4012 (2)	0.0614 (5)
H6	0.481215	0.592663	0.374640	0.074*
C7	0.56839 (12)	0.79739 (12)	0.35786 (18)	0.0507 (4)
C8	0.64717 (11)	0.72297 (11)	0.32501 (18)	0.0506 (4)
H8	0.635521	0.645689	0.329425	0.061*
C9	0.74340 (12)	0.76290 (12)	0.28553 (18)	0.0512 (4)
C10	0.83146 (12)	0.68728 (12)	0.25549 (19)	0.0513 (4)
C11	0.9112 (9)	0.7295 (10)	0.1790 (17)	0.057 (2)	0.55 (2)
H11	0.907897	0.804261	0.143525	0.069*	0.55 (2)
C12	0.9958 (11)	0.6613 (8)	0.155 (2)	0.068 (2)	0.55 (2)
H12	1.048355	0.690562	0.101752	0.081*	0.55 (2)
C13	1.00370 (15)	0.55241 (18)	0.2075 (3)	0.0773 (6)
H13	1.058653	0.505875	0.185168	0.093*	0.55 (2)
H13A	1.063604	0.507821	0.199742	0.093*	0.45 (2)
C14	0.9278 (9)	0.5113 (8)	0.296 (2)	0.083 (3)	0.55 (2)
H14	0.935968	0.438865	0.341036	0.100*	0.55 (2)
C15	0.8412 (9)	0.5772 (7)	0.3163 (19)	0.072 (2)	0.55 (2)
H15	0.789238	0.548186	0.370755	0.087*	0.55 (2)
C11A	0.9252 (10)	0.7344 (12)	0.218 (2)	0.058 (3)	0.45 (2)
H11A	0.930384	0.812190	0.207867	0.069*	0.45 (2)
C12A	1.0103 (13)	0.6668 (9)	0.195 (2)	0.069 (3)	0.45 (2)
H12A	1.072594	0.699357	0.169901	0.082*	0.45 (2)
C14A	0.9090 (7)	0.5025 (9)	0.2320 (17)	0.074 (2)	0.45 (2)
H14A	0.902589	0.424391	0.232795	0.088*	0.45 (2)
C15A	0.8235 (7)	0.5701 (7)	0.2555 (15)	0.0601 (18)	0.45 (2)
H15A	0.759370	0.536586	0.271564	0.072*	0.45 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0805 (9)	0.0365 (6)	0.1287 (12)	−0.0014 (5)	0.0508 (8)	−0.0062 (6)
O2	0.0727 (8)	0.0411 (6)	0.1168 (10)	−0.0062 (5)	0.0452 (7)	0.0035 (5)
C1	0.0495 (7)	0.0475 (8)	0.0547 (7)	0.0018 (5)	0.0173 (5)	−0.0059 (5)
C2	0.0602 (9)	0.0556 (9)	0.0809 (10)	0.0054 (7)	0.0265 (7)	−0.0134 (7)
C3	0.0596 (10)	0.0834 (13)	0.0908 (12)	0.0100 (8)	0.0335 (8)	−0.0151 (9)
C4	0.0570 (9)	0.0917 (13)	0.0782 (11)	−0.0048 (8)	0.0311 (7)	−0.0084 (9)
C5	0.0679 (10)	0.0658 (10)	0.0909 (12)	−0.0123 (8)	0.0385 (8)	−0.0051 (9)
C6	0.0593 (9)	0.0521 (9)	0.0812 (10)	−0.0025 (6)	0.0334 (7)	−0.0041 (7)
C7	0.0552 (8)	0.0402 (7)	0.0599 (8)	−0.0013 (5)	0.0197 (6)	−0.0039 (5)
C8	0.0518 (8)	0.0378 (7)	0.0669 (8)	−0.0008 (5)	0.0236 (6)	0.0000 (5)
C9	0.0543 (8)	0.0415 (7)	0.0615 (8)	−0.0028 (5)	0.0209 (6)	0.0012 (5)
C10	0.0491 (8)	0.0480 (8)	0.0616 (8)	−0.0023 (5)	0.0226 (6)	0.0015 (5)
C11	0.058 (3)	0.058 (3)	0.060 (4)	−0.006 (2)	0.021 (3)	0.002 (2)
C12	0.055 (4)	0.086 (3)	0.070 (5)	−0.005 (3)	0.032 (4)	−0.002 (3)
C13	0.0591 (9)	0.0784 (12)	0.1032 (13)	0.0110 (8)	0.0368 (9)	−0.0020 (10)
C14	0.078 (4)	0.059 (3)	0.127 (7)	0.015 (3)	0.056 (4)	0.014 (4)
C15	0.071 (4)	0.055 (3)	0.106 (6)	0.011 (2)	0.054 (4)	0.018 (3)
C11A	0.053 (3)	0.058 (3)	0.067 (7)	−0.015 (2)	0.025 (4)	−0.005 (3)
C12A	0.047 (3)	0.084 (4)	0.081 (8)	−0.011 (2)	0.026 (4)	−0.005 (3)
C14A	0.066 (3)	0.057 (3)	0.103 (6)	0.009 (2)	0.030 (3)	−0.008 (3)
C15A	0.053 (2)	0.050 (2)	0.083 (5)	−0.0021 (17)	0.027 (3)	−0.001 (3)

Geometric parameters (Å, º)

O1—H1	1.25 (3)	C10—C15	1.389 (7)
O1—C7	1.2921 (17)	C10—C11A	1.393 (10)
O2—H1	1.26 (3)	C10—C15A	1.394 (8)
O2—C9	1.2861 (17)	C11—H11	0.9300
C1—C2	1.388 (2)	C11—C12	1.379 (9)
C1—C6	1.387 (2)	C12—H12	0.9300
C1—C7	1.477 (2)	C12—C13	1.356 (9)
C2—H2	0.9300	C13—H13	0.9300
C2—C3	1.384 (3)	C13—H13A	0.9300
C3—H3	0.9300	C13—C14	1.397 (8)
C3—C4	1.369 (3)	C13—C12A	1.365 (11)
C4—H4	0.9300	C13—C14A	1.377 (9)
C4—C5	1.376 (3)	C14—H14	0.9300
C5—H5	0.9300	C14—C15	1.375 (8)
C5—C6	1.381 (2)	C15—H15	0.9300
C6—H6	0.9300	C11A—H11A	0.9300
C7—C8	1.392 (2)	C11A—C12A	1.377 (11)
C8—H8	0.9300	C12A—H12A	0.9300
C8—C9	1.3951 (19)	C14A—H14A	0.9300
C9—C10	1.482 (2)	C14A—C15A	1.382 (10)
C10—C11	1.380 (9)	C15A—H15A	0.9300
C7—O1—H1	100.7 (15)	C11A—C10—C15A	117.6 (7)
C9—O2—H1	100.1 (15)	C15A—C10—C9	123.3 (4)
C2—C1—C7	118.91 (14)	C10—C11—H11	119.8
C6—C1—C2	118.62 (14)	C12—C11—C10	120.3 (10)
C6—C1—C7	122.47 (13)	C12—C11—H11	119.8
C1—C2—H2	119.8	C11—C12—H12	119.4
C3—C2—C1	120.37 (17)	C13—C12—C11	121.2 (10)
C3—C2—H2	119.8	C13—C12—H12	119.4
C2—C3—H3	119.8	C12—C13—H13	120.6
C4—C3—C2	120.35 (16)	C12—C13—C14	118.8 (6)
C4—C3—H3	119.8	C14—C13—H13	120.6
C3—C4—H4	120.0	C12A—C13—H13A	119.8
C3—C4—C5	119.94 (16)	C12A—C13—C14A	120.5 (8)
C5—C4—H4	120.0	C14A—C13—H13A	119.8
C4—C5—H5	119.9	C13—C14—H14	119.8
C4—C5—C6	120.13 (18)	C15—C14—C13	120.5 (7)
C6—C5—H5	119.9	C15—C14—H14	119.8
C1—C6—H6	119.7	C10—C15—H15	120.0
C5—C6—C1	120.59 (16)	C14—C15—C10	120.0 (7)
C5—C6—H6	119.7	C14—C15—H15	120.0
O1—C7—C1	116.46 (13)	C10—C11A—H11A	119.7
O1—C7—C8	120.12 (13)	C12A—C11A—C10	120.7 (12)
C8—C7—C1	123.42 (13)	C12A—C11A—H11A	119.7
C7—C8—H8	119.6	C13—C12A—C11A	120.4 (12)
C7—C8—C9	120.81 (13)	C13—C12A—H12A	119.8
C9—C8—H8	119.6	C11A—C12A—H12A	119.8
O2—C9—C8	120.82 (13)	C13—C14A—H14A	120.4
O2—C9—C10	116.30 (13)	C13—C14A—C15A	119.1 (9)
C8—C9—C10	122.88 (12)	C15A—C14A—H14A	120.4
C11—C10—C9	119.5 (5)	C10—C15A—H15A	119.3
C11—C10—C15	118.9 (6)	C14A—C15A—C10	121.4 (8)
C15—C10—C9	121.3 (3)	C14A—C15A—H15A	119.3
C11A—C10—C9	119.1 (6)
O1—C7—C8—C9	−0.3 (2)	C8—C9—C10—C11	164.9 (7)
O2—C9—C10—C11	−15.9 (7)	C8—C9—C10—C15	−20.9 (8)
O2—C9—C10—C15	158.3 (8)	C8—C9—C10—C11A	−179.6 (8)
O2—C9—C10—C11A	−0.5 (8)	C8—C9—C10—C15A	3.4 (6)
O2—C9—C10—C15A	−177.5 (6)	C9—C10—C11—C12	177.9 (9)
C1—C2—C3—C4	−0.1 (3)	C9—C10—C15—C14	−175.9 (5)
C1—C7—C8—C9	−179.73 (13)	C9—C10—C11A—C12A	177.8 (10)
C2—C1—C6—C5	0.3 (3)	C9—C10—C15A—C14A	−178.0 (5)
C2—C1—C7—O1	−3.4 (2)	C10—C11—C12—C13	−0.9 (18)
C2—C1—C7—C8	176.08 (14)	C10—C11A—C12A—C13	0 (2)
C2—C3—C4—C5	0.0 (3)	C11—C10—C15—C14	−1.7 (10)
C3—C4—C5—C6	0.2 (3)	C11—C12—C13—C14	−3.6 (15)
C4—C5—C6—C1	−0.4 (3)	C12—C13—C14—C15	5.5 (11)
C6—C1—C2—C3	0.0 (3)	C13—C14—C15—C10	−2.8 (10)
C6—C1—C7—O1	176.14 (15)	C13—C14A—C15A—C10	−0.3 (11)
C6—C1—C7—C8	−4.4 (2)	C15—C10—C11—C12	3.6 (14)
C7—C1—C2—C3	179.49 (15)	C11A—C10—C15A—C14A	5.0 (10)
C7—C1—C6—C5	−179.22 (16)	C12A—C13—C14A—C15A	−4.6 (12)
C7—C8—C9—O2	−1.3 (2)	C14A—C13—C12A—C11A	4.6 (18)
C7—C8—C9—C10	177.80 (13)	C15A—C10—C11A—C12A	−5.0 (16)

(exp_3318)

Crystal data

C15H12O2	F(000) = 472
Mr = 224.25	Dx = 1.340 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
a = 12.5674 (2) Å	Cell parameters from 6709 reflections
b = 11.7596 (2) Å	θ = 3.6–76.8°
c = 7.7354 (1) Å	µ = 0.71 mm^−1
β = 103.590 (2)°	T = 100 K
V = 1111.19 (3) Å^3	Needle, yellow
Z = 4	0.54 × 0.11 × 0.10 mm

Data collection

SuperNova, Dual, Mo at zero, Atlas diffractometer	2335 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source	2145 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.035
Detector resolution: 10.4052 pixels mm^-1	θmax = 76.9°, θmin = 3.6°
ω scans	h = −15→15
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −14→14
Tmin = 0.730, Tmax = 1.000	l = −9→9
12991 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.126	w = 1/[σ^2(Fo^2) + (0.0813P)^2 + 0.1953P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2335 reflections	Δρmax = 0.21 e Å^−3
158 parameters	Δρmin = −0.27 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58655 (7)	0.90434 (6)	0.36077 (11)	0.0315 (2)
H1	0.6743 (19)	0.9068 (19)	0.323 (3)	0.083 (7)*
O2	0.76165 (7)	0.86978 (6)	0.28440 (11)	0.0300 (2)
C1	0.46472 (9)	0.75841 (9)	0.39980 (13)	0.0246 (3)
C2	0.39341 (9)	0.84083 (9)	0.43736 (15)	0.0282 (3)
H2	0.412602	0.918974	0.437620	0.034*
C3	0.29486 (9)	0.80936 (10)	0.47426 (15)	0.0305 (3)
H3	0.246917	0.865920	0.500193	0.037*
C4	0.26591 (9)	0.69516 (10)	0.47344 (15)	0.0299 (3)
H4	0.198221	0.673683	0.498508	0.036*
C5	0.33629 (10)	0.61261 (9)	0.43585 (15)	0.0303 (3)
H5	0.316566	0.534597	0.435218	0.036*
C6	0.43518 (9)	0.64354 (9)	0.39925 (14)	0.0271 (3)
H6	0.483002	0.586703	0.373744	0.033*
C7	0.56908 (9)	0.79514 (9)	0.36033 (13)	0.0248 (2)
C8	0.64712 (9)	0.71989 (8)	0.32433 (14)	0.0252 (2)
H8	0.634355	0.640260	0.324077	0.030*
C9	0.74416 (9)	0.76154 (9)	0.28859 (13)	0.0250 (2)
C10	0.83220 (9)	0.68611 (9)	0.25596 (14)	0.0251 (3)
C11	0.91855 (9)	0.73347 (9)	0.19634 (15)	0.0289 (3)
H11	0.918657	0.812729	0.172597	0.035*
C12	1.00427 (9)	0.66664 (10)	0.17117 (16)	0.0310 (3)
H12	1.062287	0.700056	0.129214	0.037*
C13	1.00574 (9)	0.55073 (10)	0.20712 (15)	0.0313 (3)
H13	1.065377	0.504956	0.192839	0.038*
C14	0.91910 (10)	0.50272 (10)	0.26407 (19)	0.0389 (3)
H14	0.919046	0.423366	0.287033	0.047*
C15	0.83260 (10)	0.56920 (10)	0.28785 (18)	0.0353 (3)
H15	0.773448	0.535163	0.325936	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0337 (4)	0.0156 (4)	0.0485 (5)	−0.0002 (3)	0.0159 (4)	−0.0013 (3)
O2	0.0319 (4)	0.0171 (4)	0.0436 (5)	−0.0013 (3)	0.0138 (3)	0.0010 (3)
C1	0.0270 (5)	0.0206 (5)	0.0259 (5)	0.0010 (4)	0.0058 (4)	−0.0013 (4)
C2	0.0303 (6)	0.0211 (5)	0.0332 (5)	0.0011 (4)	0.0075 (4)	−0.0026 (4)
C3	0.0284 (5)	0.0289 (6)	0.0353 (6)	0.0045 (4)	0.0096 (4)	−0.0028 (4)
C4	0.0263 (5)	0.0328 (6)	0.0319 (5)	−0.0023 (4)	0.0092 (4)	−0.0012 (4)
C5	0.0335 (6)	0.0240 (5)	0.0348 (6)	−0.0031 (4)	0.0106 (4)	−0.0013 (4)
C6	0.0292 (5)	0.0207 (5)	0.0332 (5)	0.0005 (4)	0.0108 (4)	−0.0008 (4)
C7	0.0292 (5)	0.0180 (5)	0.0266 (5)	−0.0009 (4)	0.0056 (4)	−0.0007 (4)
C8	0.0285 (5)	0.0173 (5)	0.0304 (5)	0.0003 (4)	0.0079 (4)	0.0003 (4)
C9	0.0287 (5)	0.0188 (5)	0.0272 (5)	−0.0001 (4)	0.0062 (4)	0.0004 (4)
C10	0.0265 (5)	0.0204 (5)	0.0286 (5)	−0.0004 (4)	0.0070 (4)	−0.0001 (4)
C11	0.0293 (5)	0.0221 (5)	0.0359 (6)	−0.0024 (4)	0.0091 (4)	0.0005 (4)
C12	0.0282 (5)	0.0289 (6)	0.0384 (6)	−0.0029 (4)	0.0125 (4)	0.0001 (4)
C13	0.0276 (5)	0.0274 (6)	0.0404 (6)	0.0035 (4)	0.0110 (4)	−0.0009 (4)
C14	0.0366 (6)	0.0223 (5)	0.0627 (8)	0.0042 (4)	0.0217 (6)	0.0056 (5)
C15	0.0336 (6)	0.0228 (5)	0.0550 (7)	0.0015 (4)	0.0215 (5)	0.0057 (5)

Geometric parameters (Å, º)

O1—H1	1.21 (2)	C7—C8	1.3967 (15)
O1—C7	1.3027 (13)	C8—H8	0.9500
O2—H1	1.28 (2)	C8—C9	1.4007 (15)
O2—C9	1.2933 (13)	C9—C10	1.4853 (15)
C1—C2	1.3962 (15)	C10—C11	1.3912 (15)
C1—C6	1.4006 (14)	C10—C15	1.3967 (15)
C1—C7	1.4792 (15)	C11—H11	0.9500
C2—H2	0.9500	C11—C12	1.3837 (16)
C2—C3	1.3851 (16)	C12—H12	0.9500
C3—H3	0.9500	C12—C13	1.3905 (16)
C3—C4	1.3910 (16)	C13—H13	0.9500
C4—H4	0.9500	C13—C14	1.3871 (16)
C4—C5	1.3894 (16)	C14—H14	0.9500
C5—H5	0.9500	C14—C15	1.3858 (16)
C5—C6	1.3865 (16)	C15—H15	0.9500
C6—H6	0.9500
C7—O1—H1	100.7 (11)	C7—C8—C9	120.17 (9)
C9—O2—H1	99.7 (10)	C9—C8—H8	119.9
C2—C1—C6	119.17 (10)	O2—C9—C8	120.67 (10)
C2—C1—C7	118.94 (10)	O2—C9—C10	116.46 (10)
C6—C1—C7	121.89 (10)	C8—C9—C10	122.86 (9)
C1—C2—H2	119.8	C11—C10—C9	119.18 (9)
C3—C2—C1	120.41 (10)	C11—C10—C15	118.81 (10)
C3—C2—H2	119.8	C15—C10—C9	121.99 (10)
C2—C3—H3	119.9	C10—C11—H11	119.6
C2—C3—C4	120.17 (10)	C12—C11—C10	120.86 (10)
C4—C3—H3	119.9	C12—C11—H11	119.6
C3—C4—H4	120.1	C11—C12—H12	119.9
C5—C4—C3	119.79 (10)	C11—C12—C13	120.19 (10)
C5—C4—H4	120.1	C13—C12—H12	119.9
C4—C5—H5	119.8	C12—C13—H13	120.4
C6—C5—C4	120.31 (10)	C14—C13—C12	119.21 (10)
C6—C5—H5	119.8	C14—C13—H13	120.4
C1—C6—H6	119.9	C13—C14—H14	119.6
C5—C6—C1	120.14 (10)	C15—C14—C13	120.76 (11)
C5—C6—H6	119.9	C15—C14—H14	119.6
O1—C7—C1	116.38 (10)	C10—C15—H15	119.9
O1—C7—C8	119.95 (10)	C14—C15—C10	120.14 (11)
C8—C7—C1	123.66 (9)	C14—C15—H15	119.9
C7—C8—H8	119.9

dibenzoylmethane (3318HAR)

Crystal data

C15H12O2	b = 11.7596 (2) Å
Mr = 224.26	c = 7.7354 (1) Å
Monoclinic, p121/c1	β = 103.590 (2)°
Hall symbol: -p 2ybc	V = 1111.19 (3) Å^3
a = 12.5674 (2) Å	Z = 4.0

Data collection

2155 independent reflections	k = →
2155 reflections with F > 0 and F/u(F) > 3.0 and |F_calc| > 10^{^−3}	l = ^→
h = ^→

Refinement

Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: HAR
wR(F^2) = 0.029	All H-atom parameters refined
S = 2.55	Weighting scheme based on measured s.u.'s w = 1/σ(F)
2155 reflections	(Δ/σ)max = 0.005
262 parameters	Δρmax = 0.12 e Å^−3
0 restraints	Δρmin = −0.15 e Å^−3

Special details

Refinement. . If constraints were applied they are defined by zero eigenvalues of the least-squares hessian, see the value of _refine_ls_SVD_threshold

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.58657 (6)	0.90405 (5)	0.36077 (9)	0.0286 (3)
H1	0.6747 (17)	0.9071 (12)	0.322 (2)	0.045 (13)
O2	0.76157 (5)	0.86952 (5)	0.28449 (9)	0.0269 (3)
C1	0.46497 (7)	0.75860 (6)	0.39971 (10)	0.0216 (4)
C2	0.39339 (7)	0.84095 (7)	0.43731 (12)	0.0256 (4)
H2	0.4195 (12)	0.9291 (12)	0.438 (2)	0.055 (10)
C3	0.29459 (7)	0.80958 (7)	0.47444 (12)	0.0279 (4)
H3	0.2409 (12)	0.8725 (11)	0.507 (2)	0.050 (9)
C4	0.26567 (7)	0.69481 (8)	0.47354 (12)	0.0272 (4)
H4	0.1884 (10)	0.6717 (11)	0.5013 (19)	0.041 (8)
C5	0.33641 (8)	0.61246 (7)	0.43571 (12)	0.0273 (4)
H5	0.3135 (12)	0.5233 (13)	0.434 (2)	0.058 (11)
C6	0.43550 (7)	0.64345 (7)	0.39923 (11)	0.0245 (4)
H6	0.4873 (11)	0.5806 (10)	0.3664 (19)	0.042 (8)
C7	0.56911 (7)	0.79529 (6)	0.36036 (10)	0.0222 (4)
C8	0.64704 (7)	0.71956 (6)	0.32435 (11)	0.0223 (4)
H8	0.6307 (12)	0.6291 (10)	0.321 (2)	0.045 (9)
C9	0.74426 (7)	0.76160 (7)	0.28841 (10)	0.0223 (4)
C10	0.83200 (7)	0.68621 (6)	0.25602 (11)	0.0222 (4)
C11	0.91840 (7)	0.73357 (7)	0.19635 (12)	0.0260 (4)
H11	0.9146 (12)	0.8250 (12)	0.170 (2)	0.053 (10)
C12	1.00438 (7)	0.66678 (8)	0.17112 (12)	0.0284 (4)
H12	1.0704 (12)	0.7019 (12)	0.120 (2)	0.051 (10)
C13	1.00593 (8)	0.55044 (7)	0.20700 (12)	0.0286 (4)
H13	1.0724 (12)	0.5010 (12)	0.190 (2)	0.052 (10)
C14	0.91915 (9)	0.50251 (8)	0.26405 (15)	0.0360 (5)
H14	0.9194 (15)	0.4145 (14)	0.298 (3)	0.082 (14)
C15	0.83231 (8)	0.56911 (7)	0.28782 (14)	0.0327 (5)
H15	0.7665 (14)	0.5325 (11)	0.337 (3)	0.067 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0304 (3)	0.0131 (3)	0.0457 (4)	−0.0001 (2)	0.0159 (3)	−0.0017 (2)
H1	0.08 (2)	0.004 (7)	0.049 (12)	−0.013 (9)	0.009 (12)	0.003 (7)
O2	0.0282 (3)	0.0141 (3)	0.0412 (4)	−0.0015 (2)	0.0136 (3)	0.0008 (2)
C1	0.0235 (4)	0.0154 (4)	0.0266 (4)	0.0001 (3)	0.0073 (3)	−0.0015 (3)
C2	0.0254 (4)	0.0186 (4)	0.0338 (4)	0.0016 (3)	0.0093 (3)	−0.0027 (3)
H2	0.047 (9)	0.031 (9)	0.086 (12)	−0.017 (7)	0.014 (9)	−0.012 (8)
C3	0.0255 (4)	0.0242 (4)	0.0357 (5)	0.0025 (3)	0.0106 (3)	−0.0027 (3)
H3	0.049 (8)	0.030 (7)	0.085 (13)	0.016 (7)	0.041 (8)	−0.005 (7)
C4	0.0244 (4)	0.0267 (4)	0.0323 (4)	−0.0016 (3)	0.0099 (3)	−0.0019 (3)
H4	0.025 (7)	0.037 (8)	0.068 (10)	−0.009 (6)	0.024 (6)	−0.001 (7)
C5	0.0284 (4)	0.0210 (4)	0.0352 (5)	−0.0035 (3)	0.0128 (3)	−0.0015 (3)
H5	0.038 (9)	0.052 (11)	0.085 (13)	−0.004 (8)	0.018 (8)	0.007 (9)
C6	0.0259 (4)	0.0162 (4)	0.0338 (4)	−0.0011 (3)	0.0115 (3)	−0.0014 (3)
H6	0.043 (7)	0.020 (6)	0.077 (11)	0.003 (6)	0.041 (7)	−0.005 (6)
C7	0.0247 (4)	0.0145 (3)	0.0282 (4)	−0.0006 (3)	0.0080 (3)	−0.0010 (3)
C8	0.0238 (4)	0.0143 (4)	0.0301 (4)	0.0003 (3)	0.0091 (3)	−0.0001 (3)
H8	0.043 (8)	0.013 (7)	0.082 (12)	−0.012 (6)	0.021 (8)	0.000 (6)
C9	0.0246 (4)	0.0152 (3)	0.0281 (4)	−0.0002 (3)	0.0082 (3)	0.0006 (3)
C10	0.0237 (4)	0.0152 (4)	0.0291 (4)	−0.0002 (3)	0.0087 (3)	0.0008 (3)
C11	0.0253 (4)	0.0187 (4)	0.0359 (4)	−0.0017 (3)	0.0111 (3)	0.0007 (3)
H11	0.047 (9)	0.028 (8)	0.089 (13)	−0.005 (7)	0.023 (8)	0.019 (8)
C12	0.0256 (4)	0.0236 (4)	0.0392 (5)	−0.0014 (3)	0.0139 (3)	0.0011 (3)
H12	0.048 (9)	0.037 (8)	0.075 (12)	−0.016 (7)	0.027 (8)	0.001 (8)
C13	0.0253 (4)	0.0225 (4)	0.0403 (5)	0.0031 (3)	0.0127 (3)	0.0004 (3)
H13	0.051 (9)	0.035 (8)	0.076 (12)	0.014 (7)	0.030 (8)	0.004 (8)
C14	0.0327 (4)	0.0188 (4)	0.0629 (6)	0.0050 (3)	0.0240 (4)	0.0059 (4)
H14	0.073 (11)	0.044 (11)	0.15 (2)	0.027 (8)	0.062 (12)	0.032 (12)
C15	0.0310 (4)	0.0170 (4)	0.0566 (6)	0.0032 (3)	0.0233 (4)	0.0066 (4)
H15	0.075 (10)	0.019 (7)	0.134 (18)	0.000 (7)	0.080 (11)	0.022 (9)

Geometric parameters (Å, º)

O1—C7	1.2975 (10)	C11—C12	1.3862 (12)
O2—C9	1.2892 (10)	C12—C13	1.3952 (12)
O1—H1	1.22 (2)	C13—C14	1.3886 (13)
O2—H1	1.27 (2)	C14—C15	1.3901 (13)
C1—C2	1.3981 (11)	C2—H2	1.086 (13)
C1—C6	1.4036 (10)	C3—H3	1.071 (12)
C1—C7	1.4761 (11)	C4—H4	1.078 (12)
C2—C3	1.3885 (12)	C5—H5	1.086 (15)
C3—C4	1.3974 (12)	C6—H6	1.055 (12)
C4—C5	1.3914 (13)	C8—H8	1.082 (12)
C5—C6	1.3886 (12)	C11—H11	1.093 (14)
C7—C8	1.3994 (11)	C12—H12	1.083 (14)
C8—C9	1.4051 (11)	C13—H13	1.052 (14)
C9—C10	1.4814 (11)	C14—H14	1.068 (16)
C10—C11	1.3920 (11)	C15—H15	1.077 (13)
C10—C15	1.3987 (11)
O1—C7—C1	116.45 (7)	C12—C13—C14	119.08 (8)
O1—C7—C8	120.13 (8)	C13—C14—C15	120.86 (8)
O2—C9—C8	120.69 (8)	C1—C2—H2	117.0 (8)
O2—C9—C10	116.67 (7)	C1—C6—H6	120.0 (7)
O1—H1—O2	158.0 (12)	C2—C3—H3	120.6 (8)
C7—O1—H1	101.1 (7)	C3—C2—H2	122.3 (8)
C9—O2—H1	100.3 (6)	C3—C4—H4	119.2 (7)
C1—C2—C3	120.62 (8)	C4—C3—H3	119.4 (8)
C1—C6—C5	120.09 (8)	C4—C5—H5	119.7 (8)
C1—C7—C8	123.43 (7)	C5—C4—H4	121.1 (7)
C2—C1—C6	119.11 (8)	C5—C6—H6	119.9 (7)
C2—C1—C7	119.04 (7)	C6—C5—H5	119.8 (8)
C2—C3—C4	119.98 (8)	C7—C8—H8	119.5 (8)
C3—C4—C5	119.67 (8)	C9—C8—H8	120.6 (8)
C4—C5—C6	120.52 (8)	C10—C11—H11	116.8 (8)
C6—C1—C7	121.85 (7)	C10—C15—H15	119.0 (7)
C7—C8—C9	119.82 (7)	C11—C12—H12	121.7 (8)
C8—C9—C10	122.63 (7)	C12—C11—H11	122.2 (8)
C9—C10—C11	119.09 (7)	C12—C13—H13	119.4 (8)
C9—C10—C15	122.07 (8)	C13—C12—H12	118.1 (8)
C10—C11—C12	120.97 (8)	C13—C14—H14	121.0 (9)
C10—C15—C14	120.09 (9)	C14—C13—H13	121.5 (8)
C11—C10—C15	118.82 (8)	C14—C15—H15	120.8 (7)
C11—C12—C13	120.16 (8)	C15—C14—H14	118.0 (9)

(exp_3421)

Crystal data

C15H12O2	Dx = 1.279 Mg m^−3
Mr = 224.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 7442 reflections
a = 8.7641 (4) Å	θ = 3.4–36.1°
b = 10.8630 (5) Å	µ = 0.08 mm^−1
c = 24.4678 (15) Å	T = 293 K
V = 2329.4 (2) Å^3	Prism, yellow
Z = 8	0.48 × 0.35 × 0.13 mm
F(000) = 944

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	3263 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2676 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.077
Detector resolution: 10.4052 pixels mm^-1	θmax = 29.6°, θmin = 2.9°
ω scans	h = −12→12
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −15→15
Tmin = 0.746, Tmax = 1.000	l = −26→33
28130 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.060	w = 1/[σ^2(Fo^2) + (0.0504P)^2 + 0.516P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.162	(Δ/σ)max < 0.001
S = 1.14	Δρmax = 0.17 e Å^−3
3263 reflections	Δρmin = −0.16 e Å^−3
159 parameters	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0133 (18)

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.83084 (15)	0.70826 (11)	0.44983 (5)	0.0720 (4)
H1	0.774 (3)	0.732 (3)	0.4017 (13)	0.148 (10)*
O2	0.70032 (16)	0.69358 (11)	0.36098 (5)	0.0736 (4)
C1	0.81204 (16)	0.55655 (14)	0.51875 (6)	0.0525 (3)
C2	0.91387 (19)	0.62188 (15)	0.55169 (7)	0.0641 (4)
H2	0.952979	0.696692	0.539641	0.077*
C3	0.9569 (2)	0.57609 (18)	0.60205 (7)	0.0714 (4)
H3	1.024658	0.620264	0.623743	0.086*
C4	0.9000 (2)	0.46556 (18)	0.62024 (7)	0.0700 (4)
H4	0.928656	0.435288	0.654274	0.084*
C5	0.8006 (2)	0.39983 (18)	0.58804 (7)	0.0680 (4)
H5	0.763218	0.324541	0.600195	0.082*
C6	0.75615 (18)	0.44475 (16)	0.53787 (6)	0.0597 (4)
H6	0.688077	0.399891	0.516577	0.072*
C7	0.76934 (17)	0.60606 (14)	0.46447 (6)	0.0545 (3)
C8	0.66694 (17)	0.54538 (14)	0.42904 (6)	0.0558 (4)
H8	0.620048	0.472972	0.440409	0.067*
C9	0.63525 (17)	0.59196 (14)	0.37767 (6)	0.0549 (4)
C10	0.53010 (17)	0.53343 (15)	0.33827 (6)	0.0549 (4)
C11	0.4749 (2)	0.60332 (18)	0.29457 (6)	0.0667 (4)
H11	0.504801	0.684999	0.290687	0.080*
C12	0.3761 (2)	0.5514 (2)	0.25715 (7)	0.0779 (5)
H12	0.339078	0.598751	0.228397	0.093*
C13	0.3318 (2)	0.4305 (2)	0.26193 (7)	0.0784 (5)
H13	0.265833	0.396103	0.236386	0.094*
C14	0.3857 (2)	0.36048 (19)	0.30479 (7)	0.0731 (5)
H14	0.356380	0.278517	0.307982	0.088*
C15	0.48329 (19)	0.41157 (16)	0.34309 (6)	0.0622 (4)
H15	0.517728	0.364103	0.372224	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0880 (8)	0.0544 (6)	0.0738 (8)	−0.0125 (6)	0.0059 (6)	−0.0058 (5)
O2	0.0957 (9)	0.0565 (7)	0.0685 (7)	−0.0045 (6)	0.0058 (6)	0.0082 (5)
C1	0.0499 (7)	0.0531 (7)	0.0546 (8)	0.0027 (6)	0.0039 (6)	−0.0132 (6)
C2	0.0619 (9)	0.0555 (8)	0.0750 (10)	−0.0017 (7)	−0.0027 (8)	−0.0148 (7)
C3	0.0663 (9)	0.0742 (9)	0.0737 (11)	−0.0004 (8)	−0.0155 (8)	−0.0217 (8)
C4	0.0721 (10)	0.0792 (10)	0.0588 (9)	0.0033 (8)	−0.0113 (7)	−0.0105 (7)
C5	0.0757 (10)	0.0709 (10)	0.0573 (9)	−0.0082 (8)	−0.0055 (7)	−0.0012 (7)
C6	0.0622 (8)	0.0629 (9)	0.0541 (8)	−0.0078 (7)	−0.0043 (7)	−0.0083 (7)
C7	0.0562 (8)	0.0497 (7)	0.0578 (8)	0.0039 (6)	0.0081 (6)	−0.0074 (6)
C8	0.0591 (8)	0.0524 (8)	0.0561 (8)	−0.0004 (6)	0.0012 (6)	0.0001 (6)
C9	0.0584 (8)	0.0510 (7)	0.0552 (8)	0.0077 (6)	0.0095 (6)	0.0005 (6)
C10	0.0571 (8)	0.0598 (8)	0.0480 (7)	0.0114 (7)	0.0058 (6)	0.0023 (6)
C11	0.0715 (10)	0.0735 (11)	0.0551 (9)	0.0111 (8)	0.0065 (7)	0.0137 (7)
C12	0.0779 (11)	0.1038 (15)	0.0519 (9)	0.0129 (11)	−0.0035 (8)	0.0195 (9)
C13	0.0791 (11)	0.1003 (15)	0.0556 (9)	0.0057 (11)	−0.0110 (8)	−0.0031 (9)
C14	0.0832 (11)	0.0725 (11)	0.0637 (10)	0.0026 (9)	−0.0102 (8)	−0.0041 (8)
C15	0.0728 (9)	0.0599 (9)	0.0537 (8)	0.0111 (8)	−0.0069 (7)	0.0017 (6)

Geometric parameters (Å, º)

O1—H1	1.30 (3)	C7—C8	1.411 (2)
O1—C7	1.2851 (19)	C8—H8	0.9300
O2—H1	1.26 (3)	C8—C9	1.383 (2)
O2—C9	1.3079 (19)	C9—C10	1.477 (2)
C1—C2	1.396 (2)	C10—C11	1.398 (2)
C1—C6	1.391 (2)	C10—C15	1.391 (2)
C1—C7	1.481 (2)	C11—H11	0.9300
C2—H2	0.9300	C11—C12	1.381 (3)
C2—C3	1.381 (2)	C12—H12	0.9300
C3—H3	0.9300	C12—C13	1.374 (3)
C3—C4	1.374 (3)	C13—H13	0.9300
C4—H4	0.9300	C13—C14	1.379 (3)
C4—C5	1.374 (2)	C14—H14	0.9300
C5—H5	0.9300	C14—C15	1.385 (2)
C5—C6	1.377 (2)	C15—H15	0.9300
C6—H6	0.9300
C7—O1—H1	105.2 (14)	C9—C8—C7	121.00 (15)
C9—O2—H1	104.9 (14)	C9—C8—H8	119.5
C2—C1—C7	119.64 (15)	O2—C9—C8	120.33 (15)
C6—C1—C2	118.35 (15)	O2—C9—C10	115.56 (14)
C6—C1—C7	121.99 (13)	C8—C9—C10	124.11 (14)
C1—C2—H2	119.8	C11—C10—C9	118.77 (16)
C3—C2—C1	120.42 (16)	C15—C10—C9	122.56 (13)
C3—C2—H2	119.8	C15—C10—C11	118.67 (16)
C2—C3—H3	119.9	C10—C11—H11	119.9
C4—C3—C2	120.30 (16)	C12—C11—C10	120.16 (18)
C4—C3—H3	119.9	C12—C11—H11	119.9
C3—C4—H4	120.1	C11—C12—H12	119.6
C5—C4—C3	119.88 (17)	C13—C12—C11	120.73 (17)
C5—C4—H4	120.1	C13—C12—H12	119.6
C4—C5—H5	119.8	C12—C13—H13	120.2
C4—C5—C6	120.41 (18)	C12—C13—C14	119.68 (19)
C6—C5—H5	119.8	C14—C13—H13	120.2
C1—C6—H6	119.7	C13—C14—H14	119.8
C5—C6—C1	120.64 (15)	C13—C14—C15	120.3 (2)
C5—C6—H6	119.7	C15—C14—H14	119.8
O1—C7—C1	117.24 (14)	C10—C15—H15	119.8
O1—C7—C8	119.94 (14)	C14—C15—C10	120.41 (15)
C8—C7—C1	122.82 (14)	C14—C15—H15	119.8
C7—C8—H8	119.5
O1—C7—C8—C9	2.3 (2)	C7—C1—C2—C3	−178.94 (14)
O2—C9—C10—C11	−17.5 (2)	C7—C1—C6—C5	178.55 (15)
O2—C9—C10—C15	162.77 (15)	C7—C8—C9—O2	0.1 (2)
C1—C2—C3—C4	0.1 (3)	C7—C8—C9—C10	179.70 (13)
C1—C7—C8—C9	−177.10 (13)	C8—C9—C10—C11	162.85 (14)
C2—C1—C6—C5	−0.1 (2)	C8—C9—C10—C15	−16.9 (2)
C2—C1—C7—O1	0.8 (2)	C9—C10—C11—C12	−179.80 (15)
C2—C1—C7—C8	−179.84 (13)	C9—C10—C15—C14	−179.36 (15)
C2—C3—C4—C5	0.4 (3)	C10—C11—C12—C13	−0.6 (3)
C3—C4—C5—C6	−0.8 (3)	C11—C10—C15—C14	0.9 (2)
C4—C5—C6—C1	0.6 (3)	C11—C12—C13—C14	0.5 (3)
C6—C1—C2—C3	−0.3 (2)	C12—C13—C14—C15	0.4 (3)
C6—C1—C7—O1	−177.87 (14)	C13—C14—C15—C10	−1.1 (3)
C6—C1—C7—C8	1.5 (2)	C15—C10—C11—C12	−0.1 (2)

(exp_3402)

Crystal data

C15H12O2	Dx = 1.339 Mg m^−3
Mr = 224.25	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 32289 reflections
a = 8.61988 (8) Å	θ = 3.4–55.1°
b = 10.62959 (10) Å	µ = 0.09 mm^−1
c = 24.2777 (3) Å	T = 100 K
V = 2224.46 (4) Å^3	Prism, yellow
Z = 8	0.50 × 0.38 × 0.12 mm
F(000) = 944

Data collection

SuperNova, Dual, Cu at zero, Atlas diffractometer	17503 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	12262 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.060
Detector resolution: 10.4052 pixels mm^-1	θmax = 61.3°, θmin = 2.9°
ω scans	h = −14→21
Absorption correction: multi-scan CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.	k = −26→25
Tmin = 0.505, Tmax = 1.000	l = −58→59
173233 measured reflections

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0734P)^2 + 0.1796P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.002
17503 reflections	Δρmax = 0.56 e Å^−3
158 parameters	Δρmin = −0.31 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15949 (4)	0.70777 (3)	0.54748 (2)	0.02082 (5)
H1	0.2152 (17)	0.7199 (14)	0.5957 (6)	0.077 (4)*
O2	0.28984 (4)	0.69700 (3)	0.63672 (2)	0.02105 (5)
C1	0.18423 (4)	0.55317 (3)	0.47789 (2)	0.01588 (5)
C2	0.07791 (5)	0.61839 (4)	0.44461 (2)	0.01878 (5)
H2	0.034986	0.695655	0.457047	0.023*
C3	0.03519 (5)	0.57028 (4)	0.39350 (2)	0.02044 (6)
H3	−0.035914	0.615187	0.370984	0.025*
C4	0.09655 (5)	0.45634 (4)	0.37530 (2)	0.02015 (6)
H4	0.067681	0.423830	0.340324	0.024*
C5	0.20015 (5)	0.39018 (4)	0.40839 (2)	0.01967 (6)
H5	0.240779	0.311928	0.396169	0.024*
C6	0.24437 (4)	0.43835 (4)	0.45933 (2)	0.01764 (5)
H6	0.315716	0.393118	0.481625	0.021*
C7	0.22524 (4)	0.60550 (3)	0.53259 (2)	0.01669 (5)
C8	0.33355 (4)	0.54480 (4)	0.56822 (2)	0.01731 (5)
H8	0.386394	0.471125	0.556437	0.021*
C9	0.36113 (4)	0.59430 (3)	0.62028 (2)	0.01609 (5)
C10	0.46985 (4)	0.53842 (3)	0.66057 (2)	0.01620 (5)
C11	0.52269 (5)	0.61314 (4)	0.70434 (2)	0.01919 (6)
H11	0.488054	0.697661	0.707594	0.023*
C12	0.62549 (5)	0.56436 (4)	0.74304 (2)	0.02189 (6)
H12	0.662302	0.616039	0.772164	0.026*
C13	0.67450 (5)	0.43963 (5)	0.73907 (2)	0.02265 (7)
H13	0.743414	0.405839	0.765786	0.027*
C14	0.62197 (5)	0.36468 (4)	0.69574 (2)	0.02137 (6)
H14	0.655196	0.279687	0.693075	0.026*
C15	0.52117 (5)	0.41364 (4)	0.65639 (2)	0.01844 (5)
H15	0.487147	0.362436	0.626676	0.022*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.02521 (12)	0.01691 (10)	0.02036 (11)	0.00430 (9)	0.00154 (9)	0.00135 (8)
O2	0.02577 (12)	0.01726 (10)	0.02011 (11)	0.00252 (9)	0.00112 (9)	−0.00191 (8)
C1	0.01532 (10)	0.01612 (10)	0.01620 (10)	−0.00009 (8)	0.00019 (8)	0.00286 (8)
C2	0.01820 (12)	0.01719 (12)	0.02096 (13)	0.00107 (9)	−0.00160 (10)	0.00348 (10)
C3	0.01943 (12)	0.02077 (13)	0.02111 (14)	0.00081 (10)	−0.00408 (10)	0.00468 (11)
C4	0.02054 (13)	0.02204 (14)	0.01787 (12)	0.00012 (11)	−0.00334 (10)	0.00204 (10)
C5	0.02108 (13)	0.02046 (13)	0.01748 (12)	0.00241 (10)	−0.00209 (10)	−0.00002 (10)
C6	0.01822 (11)	0.01843 (12)	0.01627 (11)	0.00261 (9)	−0.00119 (9)	0.00145 (9)
C7	0.01722 (11)	0.01632 (11)	0.01654 (11)	−0.00071 (8)	0.00118 (8)	0.00189 (8)
C8	0.01782 (11)	0.01757 (11)	0.01653 (11)	0.00131 (9)	−0.00103 (9)	−0.00079 (9)
C9	0.01694 (10)	0.01550 (10)	0.01583 (10)	−0.00134 (8)	0.00143 (8)	−0.00018 (8)
C10	0.01668 (10)	0.01688 (11)	0.01506 (10)	−0.00234 (8)	0.00057 (8)	−0.00107 (8)
C11	0.02066 (13)	0.02063 (13)	0.01629 (11)	−0.00228 (10)	0.00081 (9)	−0.00378 (10)
C12	0.02256 (14)	0.02719 (17)	0.01591 (12)	−0.00295 (12)	−0.00124 (10)	−0.00404 (11)
C13	0.02325 (15)	0.02724 (17)	0.01745 (13)	−0.00078 (12)	−0.00359 (11)	−0.00029 (11)
C14	0.02380 (15)	0.02078 (14)	0.01951 (13)	0.00008 (11)	−0.00384 (11)	0.00021 (10)
C15	0.02057 (12)	0.01721 (12)	0.01753 (12)	−0.00181 (9)	−0.00245 (9)	−0.00097 (9)

Geometric parameters (Å, º)

O1—H1	1.272 (16)	C7—C8	1.4270 (5)
O1—C7	1.2782 (5)	C8—H8	0.9500
O2—H1	1.210 (16)	C8—C9	1.3896 (5)
O2—C9	1.3149 (5)	C9—C10	1.4791 (5)
C1—C2	1.4046 (5)	C10—C11	1.4028 (5)
C1—C6	1.4005 (5)	C10—C15	1.4019 (5)
C1—C7	1.4826 (5)	C11—H11	0.9500
C2—H2	0.9500	C11—C12	1.3916 (6)
C2—C3	1.3917 (6)	C12—H12	0.9500
C3—H3	0.9500	C12—C13	1.3948 (7)
C3—C4	1.3935 (6)	C13—H13	0.9500
C4—H4	0.9500	C13—C14	1.3951 (6)
C4—C5	1.3919 (5)	C14—H14	0.9500
C5—H5	0.9500	C14—C15	1.3924 (6)
C5—C6	1.3917 (5)	C15—H15	0.9500
C6—H6	0.9500
C7—O1—H1	100.3 (7)	C9—C8—C7	119.48 (3)
C9—O2—H1	99.5 (7)	C9—C8—H8	120.3
C2—C1—C7	119.05 (3)	O2—C9—C8	120.71 (3)
C6—C1—C2	119.12 (3)	O2—C9—C10	115.39 (3)
C6—C1—C7	121.79 (3)	C8—C9—C10	123.91 (3)
C1—C2—H2	119.9	C11—C10—C9	118.64 (3)
C3—C2—C1	120.26 (4)	C15—C10—C9	122.14 (3)
C3—C2—H2	119.9	C15—C10—C11	119.21 (3)
C2—C3—H3	119.9	C10—C11—H11	119.8
C2—C3—C4	120.11 (3)	C12—C11—C10	120.48 (4)
C4—C3—H3	119.9	C12—C11—H11	119.8
C3—C4—H4	120.0	C11—C12—H12	120.0
C5—C4—C3	119.98 (4)	C11—C12—C13	120.03 (4)
C5—C4—H4	120.0	C13—C12—H12	120.0
C4—C5—H5	119.9	C12—C13—H13	120.1
C6—C5—C4	120.17 (4)	C12—C13—C14	119.77 (4)
C6—C5—H5	119.9	C14—C13—H13	120.1
C1—C6—H6	119.8	C13—C14—H14	119.8
C5—C6—C1	120.34 (3)	C15—C14—C13	120.43 (4)
C5—C6—H6	119.8	C15—C14—H14	119.8
O1—C7—C1	117.81 (3)	C10—C15—H15	120.0
O1—C7—C8	120.22 (3)	C14—C15—C10	120.06 (3)
C8—C7—C1	121.96 (3)	C14—C15—H15	120.0
C7—C8—H8	120.3
O1—C7—C8—C9	3.19 (5)	C7—C1—C2—C3	−178.84 (3)
O2—C9—C10—C11	−18.03 (5)	C7—C1—C6—C5	178.21 (3)
O2—C9—C10—C15	161.86 (4)	C7—C8—C9—O2	−0.75 (6)
C1—C2—C3—C4	0.67 (6)	C7—C8—C9—C10	179.50 (3)
C1—C7—C8—C9	−176.43 (3)	C8—C9—C10—C11	161.73 (4)
C2—C1—C6—C5	0.50 (6)	C8—C9—C10—C15	−18.38 (5)
C2—C1—C7—O1	1.02 (5)	C9—C10—C11—C12	−179.77 (4)
C2—C1—C7—C8	−179.35 (3)	C9—C10—C15—C14	−179.14 (4)
C2—C3—C4—C5	0.32 (6)	C10—C11—C12—C13	−1.20 (6)
C3—C4—C5—C6	−0.89 (6)	C11—C10—C15—C14	0.75 (6)
C4—C5—C6—C1	0.47 (6)	C11—C12—C13—C14	0.98 (7)
C6—C1—C2—C3	−1.07 (6)	C12—C13—C14—C15	0.11 (7)
C6—C1—C7—O1	−176.69 (3)	C13—C14—C15—C10	−0.98 (7)
C6—C1—C7—C8	2.94 (5)	C15—C10—C11—C12	0.34 (6)

dibenzoylmethane (3402HAR)

Crystal data

C15H12O2	b = 10.6296 (1) Å
Mr = 224.26	c = 24.2777 (3) Å
Orthorhombic, pbca	V = 2224.47 (4) Å^3
Hall symbol: -p 2ac 2ab	Z = 8.0
a = 8.61988 (8) Å

Data collection

12663 independent reflections	k = →
12663 reflections with F > 0 and F/u(F) > 3.0 and |F_{calc}| > 10^{^−3}	l = ^→
h = ^→

Refinement

Least-squares matrix: full	0 constraints
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: HAR
wR(F^2) = 0.024	All H-atom parameters refined
S = 2.50	Weighting scheme based on measured s.u.'s w = 1/σ(F)
12663 reflections	(Δ/σ)max = 0.003
262 parameters	Δρmax = 0.16 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Refinement. . If constraints were applied they are defined by zero eigenvalues of the least-squares hessian, see the value of _refine_ls_SVD_threshold

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.15960 (3)	0.707618 (18)	0.547447 (9)	0.01972 (9)
H1	0.2176 (7)	0.7206 (4)	0.6004 (4)	0.063 (5)
O2	0.28992 (3)	0.69682 (2)	0.636648 (10)	0.02006 (10)
C1	0.18423 (3)	0.55318 (2)	0.477898 (11)	0.01487 (10)
C2	0.07783 (3)	0.61844 (3)	0.444679 (12)	0.01774 (11)
H2	0.0243 (5)	0.7051 (4)	0.45912 (19)	0.036 (3)
C3	0.03497 (3)	0.57049 (3)	0.393539 (13)	0.01942 (12)
H3	−0.0485 (5)	0.6218 (4)	0.36972 (19)	0.040 (3)
C4	0.09646 (3)	0.45637 (3)	0.375293 (13)	0.01911 (12)
H4	0.0641 (5)	0.4207 (4)	0.33516 (19)	0.041 (3)
C5	0.20016 (3)	0.39021 (3)	0.408386 (12)	0.01861 (12)
H5	0.2476 (5)	0.3020 (4)	0.39472 (19)	0.043 (3)
C6	0.24444 (3)	0.43831 (3)	0.459339 (12)	0.01660 (11)
H6	0.3245 (5)	0.3847 (4)	0.48386 (19)	0.037 (3)
C7	0.22520 (3)	0.60556 (2)	0.532602 (12)	0.01564 (10)
C8	0.33360 (3)	0.54485 (3)	0.568207 (12)	0.01625 (11)
H8	0.3954 (5)	0.4629 (4)	0.55497 (18)	0.036 (3)
C9	0.36117 (3)	0.59437 (2)	0.620294 (11)	0.01514 (10)
C10	0.46979 (3)	0.53844 (2)	0.660545 (11)	0.01516 (10)
C11	0.52268 (3)	0.61304 (3)	0.704339 (12)	0.01821 (11)
H11	0.4820 (5)	0.7089 (4)	0.70705 (19)	0.043 (3)
C12	0.62556 (4)	0.56444 (3)	0.743089 (13)	0.02074 (13)
H12	0.6710 (5)	0.6237 (4)	0.77574 (19)	0.044 (3)
C13	0.67465 (4)	0.43955 (3)	0.739119 (13)	0.02160 (13)
H13	0.7583 (6)	0.4013 (4)	0.7684 (2)	0.042 (3)
C14	0.62201 (4)	0.36464 (3)	0.695728 (13)	0.02028 (12)
H14	0.6633 (5)	0.2688 (4)	0.69301 (19)	0.042 (3)
C15	0.52123 (3)	0.41362 (3)	0.656375 (12)	0.01741 (11)
H15	0.4833 (5)	0.3543 (4)	0.62295 (19)	0.039 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.02428 (10)	0.01614 (8)	0.01874 (10)	0.00436 (7)	0.00093 (8)	0.00144 (7)
H1	0.050 (5)	0.009 (3)	0.131 (9)	0.009 (3)	0.052 (5)	0.002 (4)
O2	0.02500 (11)	0.01644 (9)	0.01874 (10)	0.00231 (7)	0.00088 (8)	−0.00177 (7)
C1	0.01462 (10)	0.01491 (10)	0.01506 (11)	0.00010 (8)	−0.00001 (8)	0.00265 (8)
C2	0.01755 (11)	0.01609 (11)	0.01957 (13)	0.00140 (8)	−0.00185 (9)	0.00319 (9)
H2	0.038 (3)	0.025 (2)	0.045 (3)	0.013 (2)	−0.006 (2)	−0.007 (2)
C3	0.01884 (12)	0.01968 (12)	0.01975 (13)	0.00108 (9)	−0.00446 (10)	0.00436 (9)
H3	0.043 (3)	0.041 (3)	0.036 (3)	0.015 (2)	−0.014 (2)	0.010 (2)
C4	0.01985 (12)	0.02073 (12)	0.01674 (12)	0.00047 (9)	−0.00363 (10)	0.00191 (9)
H4	0.054 (3)	0.040 (3)	0.030 (3)	−0.004 (2)	−0.019 (3)	−0.007 (2)
C5	0.02041 (12)	0.01937 (11)	0.01605 (12)	0.00286 (9)	−0.00257 (9)	−0.00034 (9)
H5	0.061 (4)	0.042 (3)	0.026 (3)	0.019 (2)	−0.008 (2)	−0.008 (2)
C6	0.01754 (11)	0.01724 (11)	0.01502 (11)	0.00296 (8)	−0.00140 (9)	0.00111 (8)
H6	0.048 (3)	0.032 (3)	0.031 (3)	0.015 (2)	−0.012 (2)	−0.003 (2)
C7	0.01638 (10)	0.01529 (10)	0.01527 (11)	−0.00055 (8)	0.00100 (8)	0.00169 (8)
C8	0.01715 (11)	0.01626 (10)	0.01535 (11)	0.00137 (8)	−0.00120 (9)	−0.00088 (8)
H8	0.046 (3)	0.025 (2)	0.035 (3)	0.016 (2)	−0.014 (2)	−0.007 (2)
C9	0.01632 (10)	0.01455 (10)	0.01456 (11)	−0.00124 (8)	0.00129 (8)	−0.00038 (8)
C10	0.01594 (10)	0.01574 (10)	0.01379 (10)	−0.00211 (8)	0.00026 (8)	−0.00124 (8)
C11	0.02009 (12)	0.01944 (11)	0.01511 (11)	−0.00201 (9)	0.00044 (9)	−0.00383 (9)
H11	0.053 (3)	0.036 (3)	0.040 (3)	0.009 (2)	−0.006 (3)	−0.006 (2)
C12	0.02194 (13)	0.02547 (13)	0.01481 (12)	−0.00237 (10)	−0.00152 (10)	−0.00430 (10)
H12	0.059 (4)	0.041 (3)	0.032 (3)	−0.001 (2)	−0.015 (3)	−0.013 (2)
C13	0.02255 (13)	0.02604 (14)	0.01621 (12)	−0.00050 (10)	−0.00396 (10)	−0.00058 (10)
H13	0.045 (3)	0.049 (3)	0.032 (3)	0.006 (2)	−0.015 (3)	−0.002 (2)
C14	0.02301 (13)	0.01953 (12)	0.01831 (13)	0.00031 (10)	−0.00423 (10)	0.00027 (9)
H14	0.053 (3)	0.031 (3)	0.041 (3)	0.016 (2)	−0.009 (2)	0.002 (2)
C15	0.02005 (11)	0.01589 (10)	0.01631 (12)	−0.00161 (9)	−0.00306 (9)	−0.00102 (8)
H15	0.049 (3)	0.031 (3)	0.038 (3)	0.005 (2)	−0.019 (2)	−0.006 (2)

Geometric parameters (Å, º)

O1—C7	1.2753 (3)	C11—C12	1.3922 (4)
O2—C9	1.3118 (3)	C12—C13	1.3966 (4)
O2—H1	1.107 (9)	C13—C14	1.3963 (4)
C1—C2	1.4046 (4)	C14—C15	1.3923 (4)
C1—C6	1.4012 (4)	C2—H2	1.089 (4)
C1—C7	1.4828 (4)	C3—H3	1.072 (4)
C2—C3	1.3920 (4)	C4—H4	1.082 (4)
C3—C4	1.3960 (4)	C5—H5	1.075 (4)
C4—C5	1.3925 (4)	C6—H6	1.075 (4)
C5—C6	1.3919 (4)	C8—H8	1.071 (4)
C7—C8	1.4271 (4)	C11—H11	1.079 (4)
C8—C9	1.3902 (4)	C12—H12	1.086 (4)
C9—C10	1.4782 (4)	C13—H13	1.091 (4)
C10—C11	1.4026 (4)	C14—H14	1.082 (4)
C10—C15	1.4026 (4)	C15—H15	1.078 (4)
O1—C7—C1	117.83 (2)	C13—C14—C15	120.48 (3)
O1—C7—C8	120.25 (3)	C1—C2—H2	120.7 (2)
O2—C9—C8	120.64 (3)	C1—C6—H6	121.4 (2)
O2—C9—C10	115.49 (2)	C2—C3—H3	118.2 (2)
C9—O2—H1	102.3 (3)	C3—C2—H2	119.0 (2)
C1—C2—C3	120.30 (3)	C3—C4—H4	119.5 (2)
C1—C6—C5	120.28 (3)	C4—C3—H3	121.7 (2)
C1—C7—C8	121.92 (2)	C4—C5—H5	120.4 (2)
C2—C1—C6	119.19 (3)	C5—C4—H4	120.5 (2)
C2—C1—C7	118.97 (2)	C5—C6—H6	118.3 (2)
C2—C3—C4	120.03 (3)	C6—C5—H5	119.4 (2)
C3—C4—C5	119.97 (3)	C7—C8—H8	120.8 (2)
C4—C5—C6	120.22 (3)	C9—C8—H8	119.7 (2)
C6—C1—C7	121.80 (2)	C10—C11—H11	118.3 (2)
C7—C8—C9	119.45 (2)	C10—C15—H15	120.8 (2)
C8—C9—C10	123.87 (2)	C11—C12—H12	120.5 (2)
C9—C10—C11	118.66 (2)	C12—C11—H11	121.1 (2)
C9—C10—C15	122.21 (2)	C12—C13—H13	120.6 (2)
C10—C11—C12	120.63 (3)	C13—C12—H12	119.5 (2)
C10—C15—C14	120.09 (3)	C13—C14—H14	118.5 (2)
C11—C10—C15	119.13 (3)	C14—C13—H13	119.6 (2)
C11—C12—C13	119.94 (3)	C14—C15—H15	119.2 (2)
C12—C13—C14	119.71 (3)	C15—C14—H14	121.0 (2)