Prevalent polymorphism in benzo­phenones

We report here the crystal structures of dimorphs of 4-hy­droxy­benzo­phenone, C₁₃H₁₀O₂, and 4-(di­methyl­amino)­benzo­phenone, C₁₅H₁₅NO, as well as tri­morphs of 4,4′-di­methyl­benzo­phenone, C₁₅H₁₄O. The polymorphs were isolated from slow-evaporation conditions or from cocrystallization attempts. The main differences between the polymorphs involve differences in packing rather than differences in conformation, owing to the limited conformational freedom of the three mol­ecules. 4-Hy­droxy­benzo­phenone is the exception, exhibiting almost identical packing arrangements in the two polymorphs, with the only major changes being in the inter­planar orientations. The lattice energies of the respective polymorphs of the three compounds reported here are all within 1 kcal mol⁻¹ of each other. The existence of nine further polymorphic benzo­phenone derivatives in the literature suggests that there is a good deal of polymorphic space in this class of compounds.

Computing details

For all structures, data collection: APEX3 (Bruker, 2016); cell refinement: SAINT-Plus (Bruker, 2016); data reduction: SAINT-Plus (Bruker, 2016) and XPREP (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

4-Hydroxybenzophenone (1b)

Crystal data

C13H10O2	F(000) = 1664
Mr = 198.21	Dx = 1.298 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3013 reflections
a = 15.0087 (16) Å	θ = 2.5–24.2°
b = 13.8489 (13) Å	µ = 0.09 mm^−1
c = 19.520 (2) Å	T = 173 K
V = 4057.3 (8) Å^3	Block, colourless
Z = 16	0.5 × 0.4 × 0.3 mm

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	2612 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω scans	θmax = 28°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→16
Tmin = 0.9, Tmax = 0.95	k = −18→14
18632 measured reflections	l = −20→25
4891 independent 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)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.4555P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.131	(Δ/σ)max = 0.002
S = 1.00	Δρmax = 0.17 e Å^−3
4891 reflections	Δρmin = −0.18 e Å^−3
280 parameters	Extinction correction: SHELXL2017 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0013 (2)
0 constraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1A	0.39614 (11)	0.12693 (11)	0.35022 (9)	0.0460 (4)
C2A	0.46525 (10)	0.13139 (10)	0.29675 (9)	0.0413 (4)
C3A	0.43899 (11)	0.14662 (12)	0.22928 (9)	0.0500 (4)
H3A	0.377706	0.15702	0.219593	0.06*
C4A	0.49898 (12)	0.14704 (12)	0.17638 (9)	0.0529 (5)
H4A	0.479296	0.157855	0.130767	0.064*
C5A	0.58886 (11)	0.13155 (11)	0.18983 (9)	0.0441 (4)
C6A	0.61692 (11)	0.11526 (11)	0.25642 (9)	0.0458 (4)
H6A	0.678192	0.104128	0.265737	0.055*
C7A	0.55598 (11)	0.11521 (11)	0.30906 (9)	0.0446 (4)
H7A	0.575783	0.103991	0.354594	0.054*
C8A	0.41857 (10)	0.12688 (11)	0.42459 (9)	0.0438 (4)
C9A	0.37098 (12)	0.06686 (12)	0.46815 (10)	0.0529 (5)
H9A	0.325369	0.026589	0.450196	0.063*
C10A	0.38942 (13)	0.06529 (14)	0.53723 (10)	0.0623 (5)
H10A	0.357598	0.022768	0.566558	0.075*
C11A	0.45408 (13)	0.12540 (15)	0.56399 (10)	0.0659 (5)
H11A	0.466902	0.124115	0.611644	0.079*
C12A	0.49980 (12)	0.18704 (14)	0.52152 (9)	0.0610 (5)
H12A	0.542966	0.229789	0.540156	0.073*
C13A	0.48348 (11)	0.18728 (11)	0.45210 (9)	0.0495 (4)
H13A	0.516615	0.228776	0.422898	0.059*
O1A	0.31714 (8)	0.12074 (9)	0.33291 (7)	0.0635 (4)
O2A	0.64444 (9)	0.13251 (10)	0.13518 (7)	0.0591 (4)
H2A	0.7027 (17)	0.1237 (15)	0.1502 (12)	0.101 (8)*
C1B	0.83401 (11)	0.38026 (11)	0.15697 (9)	0.0469 (4)
C2B	0.76314 (10)	0.37519 (11)	0.20919 (9)	0.0417 (4)
C3B	0.78797 (11)	0.36388 (12)	0.27755 (9)	0.0513 (4)
H3B	0.849198	0.356149	0.288589	0.062*
C4B	0.72606 (11)	0.36367 (12)	0.32921 (9)	0.0508 (4)
H4B	0.744517	0.355016	0.375361	0.061*
C5B	0.63624 (11)	0.37612 (11)	0.31405 (8)	0.0412 (4)
C6B	0.60996 (10)	0.38798 (11)	0.24622 (8)	0.0426 (4)
H6B	0.548726	0.396281	0.235386	0.051*
C7B	0.67280 (11)	0.38769 (11)	0.19476 (8)	0.0427 (4)
H7B	0.654294	0.396152	0.14861	0.051*
C8B	0.81541 (11)	0.37715 (11)	0.08201 (9)	0.0462 (4)
C9B	0.86396 (13)	0.43717 (13)	0.03875 (10)	0.0606 (5)
H9B	0.906964	0.480187	0.057293	0.073*
C10B	0.84968 (16)	0.43431 (16)	−0.03132 (12)	0.0761 (7)
H10B	0.882148	0.476306	−0.06061	0.091*
C11B	0.78858 (16)	0.37080 (17)	−0.05880 (12)	0.0777 (7)
H11B	0.779122	0.36899	−0.1069	0.093*
C12B	0.74151 (14)	0.31030 (15)	−0.01663 (10)	0.0681 (6)
H12B	0.700338	0.265618	−0.03564	0.082*
C13B	0.75381 (11)	0.31415 (12)	0.05350 (9)	0.0524 (4)
H13B	0.71974	0.273234	0.082476	0.063*
O1B	0.91192 (8)	0.38869 (9)	0.17611 (7)	0.0668 (4)
O2B	0.57878 (9)	0.37638 (9)	0.36735 (6)	0.0538 (3)
H2B	0.5218 (16)	0.3820 (14)	0.3497 (11)	0.090 (8)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0374 (9)	0.0450 (9)	0.0556 (11)	0.0005 (7)	−0.0011 (9)	0.0006 (8)
C2A	0.0344 (8)	0.0419 (9)	0.0474 (10)	0.0012 (7)	−0.0044 (8)	0.0017 (7)
C3A	0.0327 (9)	0.0631 (11)	0.0541 (11)	0.0006 (7)	−0.0088 (9)	0.0056 (9)
C4A	0.0448 (10)	0.0702 (12)	0.0439 (10)	−0.0042 (8)	−0.0089 (9)	0.0075 (8)
C5A	0.0406 (9)	0.0487 (9)	0.0430 (10)	−0.0083 (8)	0.0008 (8)	0.0009 (8)
C6A	0.0355 (9)	0.0548 (10)	0.0471 (10)	0.0023 (7)	−0.0054 (9)	0.0012 (8)
C7A	0.0398 (9)	0.0524 (10)	0.0416 (10)	0.0046 (7)	−0.0057 (8)	0.0020 (8)
C8A	0.0359 (9)	0.0454 (9)	0.0500 (11)	0.0051 (7)	0.0054 (8)	0.0009 (8)
C9A	0.0452 (10)	0.0529 (10)	0.0604 (13)	−0.0029 (8)	0.0096 (10)	0.0010 (9)
C10A	0.0568 (12)	0.0681 (13)	0.0620 (14)	0.0028 (9)	0.0174 (11)	0.0114 (10)
C11A	0.0594 (13)	0.0940 (15)	0.0444 (11)	0.0105 (11)	0.0079 (11)	0.0008 (10)
C12A	0.0473 (11)	0.0818 (13)	0.0538 (12)	−0.0019 (9)	0.0035 (10)	−0.0141 (10)
C13A	0.0428 (10)	0.0529 (10)	0.0530 (11)	−0.0037 (8)	0.0061 (9)	−0.0013 (8)
O1A	0.0349 (7)	0.0888 (9)	0.0669 (9)	−0.0001 (6)	−0.0017 (7)	−0.0032 (7)
O2A	0.0451 (8)	0.0857 (9)	0.0465 (8)	−0.0095 (7)	0.0025 (7)	0.0025 (6)
C1B	0.0335 (9)	0.0500 (10)	0.0573 (11)	0.0028 (7)	0.0012 (9)	0.0042 (8)
C2B	0.0350 (9)	0.0446 (9)	0.0454 (10)	0.0015 (7)	−0.0011 (8)	0.0045 (7)
C3B	0.0344 (9)	0.0666 (11)	0.0528 (11)	0.0004 (8)	−0.0098 (9)	0.0077 (9)
C4B	0.0418 (10)	0.0702 (11)	0.0405 (10)	−0.0047 (8)	−0.0089 (9)	0.0085 (8)
C5B	0.0383 (9)	0.0454 (9)	0.0399 (9)	−0.0072 (7)	−0.0006 (8)	0.0013 (7)
C6B	0.0320 (8)	0.0536 (10)	0.0422 (10)	0.0000 (7)	−0.0055 (8)	0.0015 (7)
C7B	0.0374 (9)	0.0520 (10)	0.0387 (9)	0.0025 (7)	−0.0035 (8)	0.0038 (7)
C8B	0.0380 (9)	0.0499 (10)	0.0506 (11)	0.0086 (7)	0.0083 (9)	0.0052 (8)
C9B	0.0538 (11)	0.0579 (11)	0.0700 (14)	0.0054 (9)	0.0222 (11)	0.0064 (10)
C10B	0.0786 (16)	0.0812 (15)	0.0686 (15)	0.0157 (12)	0.0353 (13)	0.0211 (12)
C11B	0.0735 (15)	0.1121 (19)	0.0476 (12)	0.0252 (14)	0.0156 (12)	0.0027 (12)
C12B	0.0564 (12)	0.0930 (15)	0.0549 (13)	0.0083 (11)	0.0080 (11)	−0.0129 (11)
C13B	0.0451 (10)	0.0594 (11)	0.0527 (11)	0.0043 (8)	0.0081 (10)	0.0017 (9)
O1B	0.0343 (7)	0.0966 (10)	0.0694 (10)	−0.0019 (6)	0.0000 (7)	0.0031 (7)
O2B	0.0421 (7)	0.0790 (9)	0.0403 (7)	−0.0111 (6)	0.0009 (6)	0.0011 (6)

Geometric parameters (Å, º)

C1A—O1A	1.2359 (19)	C1B—O1B	1.2332 (19)
C1A—C2A	1.473 (2)	C1B—C2B	1.475 (2)
C1A—C8A	1.490 (2)	C1B—C8B	1.490 (2)
C2A—C3A	1.391 (2)	C2B—C3B	1.394 (2)
C2A—C7A	1.401 (2)	C2B—C7B	1.395 (2)
C3A—C4A	1.370 (2)	C3B—C4B	1.371 (2)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.391 (2)	C4B—C5B	1.391 (2)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—O2A	1.354 (2)	C5B—O2B	1.3514 (19)
C5A—C6A	1.385 (2)	C5B—C6B	1.391 (2)
C6A—C7A	1.376 (2)	C6B—C7B	1.378 (2)
C6A—H6A	0.95	C6B—H6B	0.95
C7A—H7A	0.95	C7B—H7B	0.95
C8A—C9A	1.387 (2)	C8B—C13B	1.388 (2)
C8A—C13A	1.392 (2)	C8B—C9B	1.391 (2)
C9A—C10A	1.377 (3)	C9B—C10B	1.385 (3)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C11A	1.381 (3)	C10B—C11B	1.379 (3)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.374 (3)	C11B—C12B	1.371 (3)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.377 (2)	C12B—C13B	1.382 (2)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—H13A	0.95	C13B—H13B	0.95
O2A—H2A	0.93 (2)	O2B—H2B	0.92 (2)
O1A—C1A—C2A	118.99 (16)	O1B—C1B—C2B	118.62 (17)
O1A—C1A—C8A	118.89 (15)	O1B—C1B—C8B	118.54 (16)
C2A—C1A—C8A	122.09 (14)	C2B—C1B—C8B	122.83 (15)
C3A—C2A—C7A	117.53 (16)	C3B—C2B—C7B	117.82 (15)
C3A—C2A—C1A	118.55 (15)	C3B—C2B—C1B	118.30 (15)
C7A—C2A—C1A	123.80 (15)	C7B—C2B—C1B	123.73 (15)
C4A—C3A—C2A	121.88 (16)	C4B—C3B—C2B	121.54 (15)
C4A—C3A—H3A	119.1	C4B—C3B—H3B	119.2
C2A—C3A—H3A	119.1	C2B—C3B—H3B	119.2
C3A—C4A—C5A	119.64 (16)	C3B—C4B—C5B	120.00 (16)
C3A—C4A—H4A	120.2	C3B—C4B—H4B	120
C5A—C4A—H4A	120.2	C5B—C4B—H4B	120
O2A—C5A—C6A	123.61 (15)	O2B—C5B—C4B	117.06 (15)
O2A—C5A—C4A	116.57 (16)	O2B—C5B—C6B	123.47 (15)
C6A—C5A—C4A	119.81 (16)	C4B—C5B—C6B	119.47 (16)
C7A—C6A—C5A	119.93 (15)	C7B—C6B—C5B	119.96 (15)
C7A—C6A—H6A	120	C7B—C6B—H6B	120
C5A—C6A—H6A	120	C5B—C6B—H6B	120
C6A—C7A—C2A	121.21 (16)	C6B—C7B—C2B	121.22 (15)
C6A—C7A—H7A	119.4	C6B—C7B—H7B	119.4
C2A—C7A—H7A	119.4	C2B—C7B—H7B	119.4
C9A—C8A—C13A	118.96 (17)	C13B—C8B—C9B	118.77 (17)
C9A—C8A—C1A	118.75 (15)	C13B—C8B—C1B	122.46 (15)
C13A—C8A—C1A	122.25 (15)	C9B—C8B—C1B	118.73 (16)
C10A—C9A—C8A	120.42 (17)	C10B—C9B—C8B	120.09 (19)
C10A—C9A—H9A	119.8	C10B—C9B—H9B	120
C8A—C9A—H9A	119.8	C8B—C9B—H9B	120
C9A—C10A—C11A	120.14 (18)	C11B—C10B—C9B	120.3 (2)
C9A—C10A—H10A	119.9	C11B—C10B—H10B	119.8
C11A—C10A—H10A	119.9	C9B—C10B—H10B	119.8
C12A—C11A—C10A	119.82 (19)	C12B—C11B—C10B	119.9 (2)
C12A—C11A—H11A	120.1	C12B—C11B—H11B	120
C10A—C11A—H11A	120.1	C10B—C11B—H11B	120
C11A—C12A—C13A	120.43 (18)	C11B—C12B—C13B	120.2 (2)
C11A—C12A—H12A	119.8	C11B—C12B—H12B	119.9
C13A—C12A—H12A	119.8	C13B—C12B—H12B	119.9
C12A—C13A—C8A	120.18 (17)	C12B—C13B—C8B	120.69 (18)
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.7
C8A—C13A—H13A	119.9	C8B—C13B—H13B	119.7
C5A—O2A—H2A	109.3 (15)	C5B—O2B—H2B	107.6 (14)
O1A—C1A—C2A—C3A	11.8 (2)	O1B—C1B—C2B—C3B	−10.6 (2)
C8A—C1A—C2A—C3A	−169.90 (14)	C8B—C1B—C2B—C3B	170.41 (15)
O1A—C1A—C2A—C7A	−164.03 (15)	O1B—C1B—C2B—C7B	164.86 (15)
C8A—C1A—C2A—C7A	14.2 (2)	C8B—C1B—C2B—C7B	−14.2 (2)
C7A—C2A—C3A—C4A	−0.7 (2)	C7B—C2B—C3B—C4B	0.8 (2)
C1A—C2A—C3A—C4A	−176.83 (15)	C1B—C2B—C3B—C4B	176.54 (15)
C2A—C3A—C4A—C5A	0.2 (3)	C2B—C3B—C4B—C5B	−0.8 (3)
C3A—C4A—C5A—O2A	179.73 (14)	C3B—C4B—C5B—O2B	−179.21 (15)
C3A—C4A—C5A—C6A	0.4 (3)	C3B—C4B—C5B—C6B	0.5 (2)
O2A—C5A—C6A—C7A	−179.81 (14)	O2B—C5B—C6B—C7B	179.43 (14)
C4A—C5A—C6A—C7A	−0.5 (2)	C4B—C5B—C6B—C7B	−0.2 (2)
C5A—C6A—C7A—C2A	0.0 (2)	C5B—C6B—C7B—C2B	0.3 (2)
C3A—C2A—C7A—C6A	0.6 (2)	C3B—C2B—C7B—C6B	−0.6 (2)
C1A—C2A—C7A—C6A	176.48 (15)	C1B—C2B—C7B—C6B	−176.03 (14)
O1A—C1A—C8A—C9A	38.5 (2)	O1B—C1B—C8B—C13B	138.64 (17)
C2A—C1A—C8A—C9A	−139.73 (16)	C2B—C1B—C8B—C13B	−42.3 (2)
O1A—C1A—C8A—C13A	−139.24 (16)	O1B—C1B—C8B—C9B	−39.0 (2)
C2A—C1A—C8A—C13A	42.5 (2)	C2B—C1B—C8B—C9B	140.08 (16)
C13A—C8A—C9A—C10A	−1.7 (2)	C13B—C8B—C9B—C10B	0.8 (3)
C1A—C8A—C9A—C10A	−179.59 (15)	C1B—C8B—C9B—C10B	178.49 (16)
C8A—C9A—C10A—C11A	1.6 (3)	C8B—C9B—C10B—C11B	−1.2 (3)
C9A—C10A—C11A—C12A	0.2 (3)	C9B—C10B—C11B—C12B	0.2 (3)
C10A—C11A—C12A—C13A	−1.9 (3)	C10B—C11B—C12B—C13B	1.3 (3)
C11A—C12A—C13A—C8A	1.8 (3)	C11B—C12B—C13B—C8B	−1.7 (3)
C9A—C8A—C13A—C12A	0.0 (2)	C9B—C8B—C13B—C12B	0.7 (2)
C1A—C8A—C13A—C12A	177.78 (15)	C1B—C8B—C13B—C12B	−176.92 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2A—H2A···O1A^i	0.93 (2)	1.75 (3)	2.6707 (18)	170 (2)
O2B—H2B···O1B^ii	0.92 (2)	1.73 (2)	2.6497 (18)	175 (2)

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

4-(Dimethylamino)benzophenone (2a)

Crystal data

C15H15NO	F(000) = 960
Mr = 225.28	Dx = 1.25 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9955 reflections
a = 7.7442 (3) Å	θ = 3.1–30.0°
b = 11.7730 (4) Å	µ = 0.08 mm^−1
c = 26.2562 (11) Å	T = 173 K
V = 2393.84 (16) Å^3	Plate, yellow
Z = 8	0.39 × 0.37 × 0.03 mm

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	5097 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 28.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.95, Tmax = 0.96	k = −14→15
28492 measured reflections	l = −34→26
5769 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.035	w = 1/[σ^2(Fo^2) + (0.0356P)^2 + 0.4214P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.083	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.21 e Å^−3
5769 reflections	Δρmin = −0.17 e Å^−3
311 parameters	Absolute structure: Flack x determined using 2027 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.2 (4)
0 constraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1A	0.9880 (2)	0.72925 (15)	0.87067 (7)	0.0295 (4)
C2A	0.9708 (2)	0.68645 (14)	0.92317 (6)	0.0253 (4)
C3A	1.0373 (2)	0.75073 (15)	0.96336 (7)	0.0283 (4)
H3A	1.092793	0.820835	0.95605	0.034*
C4A	1.0251 (2)	0.71570 (15)	1.01305 (7)	0.0283 (4)
H4A	1.074983	0.760506	1.039297	0.034*
C5A	0.9390 (2)	0.61378 (14)	1.02561 (7)	0.0255 (3)
C6A	0.8671 (2)	0.55045 (15)	0.98527 (7)	0.0263 (4)
H6A	0.805215	0.482666	0.992477	0.032*
C7A	0.8856 (2)	0.58568 (14)	0.93553 (7)	0.0265 (4)
H7A	0.839192	0.540199	0.908963	0.032*
C8A	0.9951 (2)	0.64790 (14)	0.82686 (6)	0.0262 (4)
C9A	0.9298 (2)	0.68138 (15)	0.77975 (7)	0.0311 (4)
H9A	0.869899	0.751468	0.776697	0.037*
C10A	0.9519 (3)	0.61281 (16)	0.73730 (7)	0.0327 (4)
H10A	0.906259	0.635828	0.705338	0.039*
C11A	1.0399 (3)	0.51114 (17)	0.74132 (7)	0.0338 (4)
H11A	1.056339	0.464901	0.712069	0.041*
C12A	1.1040 (3)	0.47681 (16)	0.78801 (7)	0.0339 (4)
H12A	1.164325	0.406813	0.790799	0.041*
C13A	1.0806 (2)	0.54423 (15)	0.83076 (7)	0.0288 (4)
H13A	1.123096	0.519559	0.862847	0.035*
C14A	0.9873 (3)	0.65027 (18)	1.11634 (8)	0.0445 (5)
H14A	0.917866	0.719808	1.117543	0.067*
H14B	1.108687	0.670004	1.110572	0.067*
H14C	0.976344	0.609539	1.148733	0.067*
C15A	0.8156 (3)	0.48326 (16)	1.08833 (8)	0.0364 (4)
H15A	0.85512	0.414966	1.070449	0.055*
H15B	0.69659	0.500409	1.078251	0.055*
H15C	0.820289	0.47028	1.125169	0.055*
N1A	0.9267 (2)	0.57839 (13)	1.07514 (6)	0.0325 (4)
O1A	1.0017 (2)	0.83145 (11)	0.86187 (5)	0.0443 (4)
C1B	0.4970 (2)	0.45981 (15)	0.87197 (7)	0.0282 (4)
C2B	0.4656 (2)	0.42116 (14)	0.92482 (7)	0.0257 (4)
C3B	0.3778 (2)	0.49240 (15)	0.95897 (7)	0.0288 (4)
H3B	0.332509	0.562473	0.947006	0.035*
C4B	0.3558 (2)	0.46366 (15)	1.00906 (7)	0.0292 (4)
H4B	0.293808	0.513324	1.030941	0.035*
C5B	0.4239 (2)	0.36120 (14)	1.02879 (7)	0.0256 (4)
C6B	0.5146 (2)	0.29020 (15)	0.99478 (7)	0.0280 (4)
H6B	0.563773	0.221291	1.006794	0.034*
C7B	0.5326 (2)	0.31994 (15)	0.94424 (7)	0.0275 (4)
H7B	0.592519	0.270028	0.921962	0.033*
C8B	0.5349 (2)	0.37493 (15)	0.83073 (7)	0.0270 (4)
C9B	0.6444 (2)	0.40684 (17)	0.79131 (7)	0.0333 (4)
H9B	0.697548	0.479568	0.791907	0.04*
C10B	0.6769 (3)	0.33363 (19)	0.75118 (7)	0.0392 (5)
H10B	0.753924	0.355647	0.724818	0.047*
C11B	0.5973 (3)	0.22838 (18)	0.74936 (7)	0.0372 (5)
H11B	0.618074	0.178672	0.721528	0.045*
C12B	0.4876 (3)	0.19603 (16)	0.78817 (7)	0.0346 (4)
H12B	0.432629	0.123939	0.786929	0.042*
C13B	0.4570 (2)	0.26834 (15)	0.82908 (7)	0.0301 (4)
H13B	0.382899	0.244999	0.855941	0.036*
C14B	0.3137 (3)	0.40881 (17)	1.11361 (7)	0.0349 (4)
H14D	0.197406	0.424258	1.100587	0.052*
H14E	0.378067	0.480216	1.116274	0.052*
H14F	0.305331	0.373454	1.147308	0.052*
C15B	0.4779 (3)	0.22892 (17)	1.09902 (7)	0.0391 (5)
H15D	0.6038	0.231947	1.095478	0.059*
H15E	0.433021	0.163552	1.080074	0.059*
H15F	0.447589	0.221262	1.135091	0.059*
N1B	0.4030 (2)	0.33234 (13)	1.07893 (6)	0.0316 (3)
O2B	0.4932 (2)	0.56092 (11)	0.86123 (5)	0.0393 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0321 (9)	0.0253 (9)	0.0311 (9)	0.0022 (8)	−0.0017 (7)	0.0006 (7)
C2A	0.0257 (8)	0.0216 (8)	0.0286 (8)	0.0023 (7)	0.0000 (7)	−0.0012 (7)
C3A	0.0296 (8)	0.0215 (8)	0.0339 (9)	−0.0039 (7)	0.0005 (7)	−0.0013 (7)
C4A	0.0301 (8)	0.0258 (8)	0.0291 (9)	−0.0042 (8)	−0.0036 (7)	−0.0055 (7)
C5A	0.0239 (8)	0.0230 (8)	0.0295 (8)	0.0037 (7)	0.0003 (7)	−0.0016 (7)
C6A	0.0267 (8)	0.0208 (8)	0.0316 (9)	−0.0030 (7)	0.0001 (7)	−0.0012 (7)
C7A	0.0265 (8)	0.0227 (8)	0.0302 (9)	−0.0004 (7)	−0.0034 (7)	−0.0052 (7)
C8A	0.0274 (8)	0.0246 (8)	0.0267 (8)	−0.0031 (7)	0.0006 (7)	0.0014 (7)
C9A	0.0338 (9)	0.0265 (9)	0.0328 (9)	0.0004 (8)	−0.0003 (8)	0.0058 (7)
C10A	0.0376 (10)	0.0368 (10)	0.0238 (9)	−0.0056 (9)	−0.0017 (8)	0.0059 (8)
C11A	0.0372 (10)	0.0361 (10)	0.0282 (9)	−0.0050 (9)	0.0046 (8)	−0.0053 (8)
C12A	0.0354 (10)	0.0305 (9)	0.0358 (10)	0.0050 (8)	0.0019 (8)	−0.0022 (8)
C13A	0.0297 (9)	0.0286 (9)	0.0281 (9)	0.0011 (8)	−0.0024 (7)	0.0020 (7)
C14A	0.0626 (14)	0.0413 (11)	0.0294 (10)	−0.0080 (11)	−0.0029 (10)	−0.0045 (8)
C15A	0.0454 (11)	0.0284 (10)	0.0354 (10)	−0.0001 (9)	0.0028 (9)	0.0066 (8)
N1A	0.0398 (9)	0.0299 (8)	0.0277 (8)	−0.0055 (7)	−0.0010 (7)	−0.0006 (6)
O1A	0.0741 (11)	0.0222 (6)	0.0366 (7)	−0.0011 (7)	−0.0003 (8)	0.0026 (5)
C1B	0.0240 (8)	0.0268 (9)	0.0339 (9)	−0.0006 (8)	−0.0028 (7)	0.0005 (7)
C2B	0.0229 (8)	0.0248 (8)	0.0295 (8)	−0.0014 (7)	−0.0011 (7)	−0.0021 (7)
C3B	0.0301 (8)	0.0214 (8)	0.0349 (9)	0.0036 (7)	−0.0034 (8)	−0.0012 (7)
C4B	0.0285 (9)	0.0243 (9)	0.0349 (10)	0.0032 (7)	0.0012 (7)	−0.0066 (7)
C5B	0.0223 (8)	0.0237 (8)	0.0309 (9)	−0.0028 (7)	−0.0020 (7)	−0.0034 (7)
C6B	0.0268 (8)	0.0221 (8)	0.0350 (9)	0.0027 (7)	−0.0011 (7)	0.0015 (7)
C7B	0.0247 (8)	0.0250 (8)	0.0329 (9)	0.0029 (7)	0.0008 (7)	−0.0033 (7)
C8B	0.0229 (8)	0.0298 (9)	0.0283 (9)	0.0012 (7)	−0.0035 (7)	0.0014 (7)
C9B	0.0318 (9)	0.0365 (10)	0.0317 (9)	−0.0043 (8)	−0.0013 (8)	0.0033 (8)
C10B	0.0362 (10)	0.0515 (13)	0.0298 (10)	−0.0030 (10)	0.0043 (8)	0.0012 (9)
C11B	0.0368 (10)	0.0452 (12)	0.0296 (9)	0.0050 (10)	−0.0032 (8)	−0.0070 (8)
C12B	0.0355 (10)	0.0317 (9)	0.0368 (10)	−0.0018 (9)	−0.0066 (8)	−0.0038 (8)
C13B	0.0272 (9)	0.0310 (9)	0.0321 (9)	−0.0005 (7)	0.0009 (7)	0.0021 (7)
C14B	0.0376 (10)	0.0366 (10)	0.0306 (10)	−0.0053 (9)	0.0035 (8)	−0.0058 (8)
C15B	0.0461 (11)	0.0349 (10)	0.0364 (10)	0.0000 (10)	−0.0057 (9)	0.0059 (8)
N1B	0.0368 (8)	0.0279 (8)	0.0301 (8)	−0.0004 (7)	0.0012 (7)	−0.0011 (6)
O2B	0.0503 (9)	0.0269 (7)	0.0408 (8)	0.0010 (7)	0.0021 (7)	0.0042 (6)

Geometric parameters (Å, º)

C1A—O1A	1.230 (2)	C1B—O2B	1.224 (2)
C1A—C2A	1.474 (2)	C1B—C2B	1.480 (2)
C1A—C8A	1.498 (2)	C1B—C8B	1.502 (2)
C2A—C7A	1.396 (2)	C2B—C7B	1.396 (2)
C2A—C3A	1.397 (2)	C2B—C3B	1.403 (2)
C3A—C4A	1.372 (2)	C3B—C4B	1.369 (3)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.412 (2)	C4B—C5B	1.415 (2)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—N1A	1.369 (2)	C5B—N1B	1.369 (2)
C5A—C6A	1.410 (2)	C5B—C6B	1.411 (2)
C6A—C7A	1.378 (2)	C6B—C7B	1.380 (2)
C6A—H6A	0.95	C6B—H6B	0.95
C7A—H7A	0.95	C7B—H7B	0.95
C8A—C13A	1.392 (2)	C8B—C9B	1.390 (3)
C8A—C9A	1.393 (2)	C8B—C13B	1.393 (3)
C9A—C10A	1.387 (3)	C9B—C10B	1.384 (3)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C11A	1.381 (3)	C10B—C11B	1.385 (3)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.383 (3)	C11B—C12B	1.380 (3)
C11A—H11A	0.95	C11B—H11B	0.95
C12A—C13A	1.387 (3)	C12B—C13B	1.391 (3)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—H13A	0.95	C13B—H13B	0.95
C14A—N1A	1.452 (2)	C14B—N1B	1.455 (2)
C14A—H14A	0.98	C14B—H14D	0.98
C14A—H14B	0.98	C14B—H14E	0.98
C14A—H14C	0.98	C14B—H14F	0.98
C15A—N1A	1.454 (2)	C15B—N1B	1.448 (2)
C15A—H15A	0.98	C15B—H15D	0.98
C15A—H15B	0.98	C15B—H15E	0.98
C15A—H15C	0.98	C15B—H15F	0.98
O1A—C1A—C2A	121.20 (16)	O2B—C1B—C2B	120.74 (16)
O1A—C1A—C8A	118.57 (16)	O2B—C1B—C8B	119.05 (16)
C2A—C1A—C8A	120.20 (15)	C2B—C1B—C8B	120.21 (15)
C7A—C2A—C3A	117.34 (16)	C7B—C2B—C3B	117.17 (16)
C7A—C2A—C1A	123.44 (15)	C7B—C2B—C1B	122.92 (15)
C3A—C2A—C1A	119.19 (15)	C3B—C2B—C1B	119.66 (15)
C4A—C3A—C2A	122.00 (16)	C4B—C3B—C2B	121.78 (17)
C4A—C3A—H3A	119	C4B—C3B—H3B	119.1
C2A—C3A—H3A	119	C2B—C3B—H3B	119.1
C3A—C4A—C5A	120.69 (16)	C3B—C4B—C5B	121.08 (16)
C3A—C4A—H4A	119.7	C3B—C4B—H4B	119.5
C5A—C4A—H4A	119.7	C5B—C4B—H4B	119.5
N1A—C5A—C6A	121.67 (16)	N1B—C5B—C6B	121.35 (16)
N1A—C5A—C4A	120.90 (16)	N1B—C5B—C4B	121.31 (16)
C6A—C5A—C4A	117.42 (16)	C6B—C5B—C4B	117.33 (16)
C7A—C6A—C5A	120.79 (16)	C7B—C6B—C5B	120.59 (16)
C7A—C6A—H6A	119.6	C7B—C6B—H6B	119.7
C5A—C6A—H6A	119.6	C5B—C6B—H6B	119.7
C6A—C7A—C2A	121.70 (16)	C6B—C7B—C2B	122.02 (16)
C6A—C7A—H7A	119.2	C6B—C7B—H7B	119
C2A—C7A—H7A	119.2	C2B—C7B—H7B	119
C13A—C8A—C9A	119.07 (16)	C9B—C8B—C13B	118.98 (17)
C13A—C8A—C1A	121.45 (16)	C9B—C8B—C1B	118.44 (17)
C9A—C8A—C1A	119.17 (16)	C13B—C8B—C1B	122.48 (16)
C10A—C9A—C8A	120.27 (17)	C10B—C9B—C8B	120.61 (19)
C10A—C9A—H9A	119.9	C10B—C9B—H9B	119.7
C8A—C9A—H9A	119.9	C8B—C9B—H9B	119.7
C11A—C10A—C9A	120.25 (17)	C9B—C10B—C11B	120.18 (19)
C11A—C10A—H10A	119.9	C9B—C10B—H10B	119.9
C9A—C10A—H10A	119.9	C11B—C10B—H10B	119.9
C10A—C11A—C12A	119.88 (17)	C12B—C11B—C10B	119.70 (18)
C10A—C11A—H11A	120.1	C12B—C11B—H11B	120.2
C12A—C11A—H11A	120.1	C10B—C11B—H11B	120.2
C11A—C12A—C13A	120.21 (18)	C11B—C12B—C13B	120.39 (18)
C11A—C12A—H12A	119.9	C11B—C12B—H12B	119.8
C13A—C12A—H12A	119.9	C13B—C12B—H12B	119.8
C12A—C13A—C8A	120.30 (17)	C12B—C13B—C8B	120.12 (17)
C12A—C13A—H13A	119.8	C12B—C13B—H13B	119.9
C8A—C13A—H13A	119.8	C8B—C13B—H13B	119.9
N1A—C14A—H14A	109.5	N1B—C14B—H14D	109.5
N1A—C14A—H14B	109.5	N1B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
N1A—C14A—H14C	109.5	N1B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
N1A—C15A—H15A	109.5	N1B—C15B—H15D	109.5
N1A—C15A—H15B	109.5	N1B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
N1A—C15A—H15C	109.5	N1B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
C5A—N1A—C14A	120.52 (16)	C5B—N1B—C15B	120.77 (15)
C5A—N1A—C15A	120.14 (16)	C5B—N1B—C14B	120.27 (15)
C14A—N1A—C15A	117.59 (16)	C15B—N1B—C14B	118.86 (15)
O1A—C1A—C2A—C7A	152.08 (19)	O2B—C1B—C2B—C7B	−153.45 (18)
C8A—C1A—C2A—C7A	−30.0 (3)	C8B—C1B—C2B—C7B	26.2 (3)
O1A—C1A—C2A—C3A	−25.7 (3)	O2B—C1B—C2B—C3B	20.7 (3)
C8A—C1A—C2A—C3A	152.20 (17)	C8B—C1B—C2B—C3B	−159.58 (16)
C7A—C2A—C3A—C4A	1.9 (3)	C7B—C2B—C3B—C4B	−1.1 (3)
C1A—C2A—C3A—C4A	179.85 (17)	C1B—C2B—C3B—C4B	−175.59 (17)
C2A—C3A—C4A—C5A	−1.9 (3)	C2B—C3B—C4B—C5B	1.2 (3)
C3A—C4A—C5A—N1A	179.90 (17)	C3B—C4B—C5B—N1B	179.65 (17)
C3A—C4A—C5A—C6A	0.0 (3)	C3B—C4B—C5B—C6B	−0.1 (3)
N1A—C5A—C6A—C7A	−177.96 (17)	N1B—C5B—C6B—C7B	179.21 (17)
C4A—C5A—C6A—C7A	2.0 (3)	C4B—C5B—C6B—C7B	−1.0 (3)
C5A—C6A—C7A—C2A	−2.0 (3)	C5B—C6B—C7B—C2B	1.1 (3)
C3A—C2A—C7A—C6A	0.1 (3)	C3B—C2B—C7B—C6B	−0.1 (3)
C1A—C2A—C7A—C6A	−177.77 (17)	C1B—C2B—C7B—C6B	174.23 (17)
O1A—C1A—C8A—C13A	140.9 (2)	O2B—C1B—C8B—C9B	32.1 (3)
C2A—C1A—C8A—C13A	−37.1 (3)	C2B—C1B—C8B—C9B	−147.61 (17)
O1A—C1A—C8A—C9A	−32.7 (3)	O2B—C1B—C8B—C13B	−144.20 (19)
C2A—C1A—C8A—C9A	149.31 (17)	C2B—C1B—C8B—C13B	36.1 (2)
C13A—C8A—C9A—C10A	−0.8 (3)	C13B—C8B—C9B—C10B	−0.5 (3)
C1A—C8A—C9A—C10A	172.88 (17)	C1B—C8B—C9B—C10B	−176.91 (18)
C8A—C9A—C10A—C11A	−0.5 (3)	C8B—C9B—C10B—C11B	1.4 (3)
C9A—C10A—C11A—C12A	1.0 (3)	C9B—C10B—C11B—C12B	−1.0 (3)
C10A—C11A—C12A—C13A	−0.2 (3)	C10B—C11B—C12B—C13B	−0.2 (3)
C11A—C12A—C13A—C8A	−1.2 (3)	C11B—C12B—C13B—C8B	1.1 (3)
C9A—C8A—C13A—C12A	1.6 (3)	C9B—C8B—C13B—C12B	−0.7 (3)
C1A—C8A—C13A—C12A	−171.92 (17)	C1B—C8B—C13B—C12B	175.54 (17)
C6A—C5A—N1A—C14A	−174.15 (19)	C6B—C5B—N1B—C15B	1.7 (3)
C4A—C5A—N1A—C14A	5.9 (3)	C4B—C5B—N1B—C15B	−178.07 (17)
C6A—C5A—N1A—C15A	−9.6 (3)	C6B—C5B—N1B—C14B	178.01 (17)
C4A—C5A—N1A—C15A	170.48 (16)	C4B—C5B—N1B—C14B	−1.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C14B—H14E···O1A^i	0.98	2.48	3.448 (2)	168

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

4,4'-Dimethylbenzophenone (3a)

Crystal data

C15H14O	Dx = 1.206 Mg m^−3
Mr = 210.26	Mo Kα radiation, λ = 0.71073 Å
Trigonal, P3221	Cell parameters from 1026 reflections
Hall symbol: P 32 2"	θ = 2.5–28.2°
a = 9.4796 (14) Å	µ = 0.07 mm^−1
c = 11.164 (3) Å	T = 173 K
V = 868.8 (3) Å^3	Plate, colourless
Z = 3	0.43 × 0.17 × 0.05 mm
F(000) = 336

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	1201 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 28.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→4
Tmin = 0.95, Tmax = 0.96	k = −10→11
2540 measured reflections	l = −14→10
1411 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0484P)^2 + 0.1427P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.113	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.17 e Å^−3
1411 reflections	Δρmin = −0.13 e Å^−3
75 parameters	Absolute structure: Flack x determined using 434 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.1 (10)
0 constraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1	0.2106 (3)	1.2106 (3)	1	0.0379 (7)
C2	0.2064 (2)	1.0578 (2)	0.96154 (18)	0.0337 (5)
C3	0.3217 (3)	1.0669 (3)	0.8794 (2)	0.0451 (6)
H3	0.397027	1.169024	0.845101	0.054*
C4	0.3275 (3)	0.9289 (3)	0.8472 (2)	0.0459 (6)
H4	0.406007	0.937522	0.790289	0.055*
C5	0.2205 (3)	0.7781 (3)	0.89675 (19)	0.0394 (5)
C6	0.1066 (3)	0.7692 (3)	0.97962 (18)	0.0394 (5)
H6	0.03393	0.667482	1.015751	0.047*
C7	0.0974 (3)	0.9062 (3)	1.01046 (17)	0.0349 (5)
H7	0.016306	0.896735	1.065189	0.042*
C8	0.2281 (3)	0.6273 (4)	0.8628 (3)	0.0572 (7)
H8A	0.317531	0.626456	0.906303	0.086*
H8B	0.246834	0.628005	0.776436	0.086*
H8C	0.125013	0.529904	0.883801	0.086*
O1	0.3395 (2)	1.3395 (2)	1	0.0605 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0316 (11)	0.0316 (11)	0.0439 (16)	0.0109 (12)	−0.0062 (7)	0.0062 (7)
C2	0.0253 (10)	0.0354 (10)	0.0354 (9)	0.0115 (8)	−0.0049 (8)	0.0042 (8)
C3	0.0265 (11)	0.0511 (14)	0.0551 (14)	0.0174 (10)	0.0059 (10)	0.0187 (11)
C4	0.0323 (12)	0.0674 (16)	0.0444 (12)	0.0297 (12)	0.0072 (10)	0.0098 (11)
C5	0.0338 (11)	0.0509 (13)	0.0373 (10)	0.0241 (11)	−0.0052 (9)	−0.0048 (10)
C6	0.0383 (11)	0.0355 (11)	0.0388 (10)	0.0142 (10)	0.0040 (9)	−0.0008 (9)
C7	0.0357 (11)	0.0341 (10)	0.0307 (9)	0.0142 (9)	0.0033 (8)	0.0004 (8)
C8	0.0505 (15)	0.0633 (17)	0.0660 (17)	0.0345 (14)	0.0013 (14)	−0.0144 (14)
O1	0.0344 (9)	0.0344 (9)	0.0993 (19)	0.0070 (11)	−0.0050 (7)	0.0050 (7)

Geometric parameters (Å, º)

C1—O1	1.222 (4)	C5—C6	1.392 (3)
C1—C2^i	1.492 (3)	C5—C8	1.515 (4)
C1—C2	1.492 (3)	C6—C7	1.389 (3)
C2—C7	1.395 (3)	C6—H6	0.95
C2—C3	1.396 (3)	C7—H7	0.95
C3—C4	1.384 (4)	C8—H8A	0.98
C3—H3	0.95	C8—H8B	0.98
C4—C5	1.389 (3)	C8—H8C	0.98
C4—H4	0.95
O1—C1—C2^i	119.9 (3)	C6—C5—C8	120.7 (2)
O1—C1—C2	119.9 (3)	C7—C6—C5	121.2 (2)
C2^i—C1—C2	120.2 (3)	C7—C6—H6	119.4
C7—C2—C3	118.4 (2)	C5—C6—H6	119.4
C7—C2—C1	122.2 (2)	C6—C7—C2	120.4 (2)
C3—C2—C1	119.3 (2)	C6—C7—H7	119.8
C4—C3—C2	120.8 (2)	C2—C7—H7	119.8
C4—C3—H3	119.6	C5—C8—H8A	109.5
C2—C3—H3	119.6	C5—C8—H8B	109.5
C3—C4—C5	121.0 (2)	H8A—C8—H8B	109.5
C3—C4—H4	119.5	C5—C8—H8C	109.5
C5—C4—H4	119.5	H8A—C8—H8C	109.5
C4—C5—C6	118.2 (2)	H8B—C8—H8C	109.5
C4—C5—C8	121.1 (2)
O1—C1—C2—C7	147.66 (15)	C3—C4—C5—C6	0.2 (3)
C2^i—C1—C2—C7	−32.34 (15)	C3—C4—C5—C8	−179.2 (2)
O1—C1—C2—C3	−28.2 (2)	C4—C5—C6—C7	1.3 (3)
C2^i—C1—C2—C3	151.8 (2)	C8—C5—C6—C7	−179.3 (2)
C7—C2—C3—C4	0.0 (3)	C5—C6—C7—C2	−2.1 (3)
C1—C2—C3—C4	176.10 (19)	C3—C2—C7—C6	1.4 (3)
C2—C3—C4—C5	−0.8 (4)	C1—C2—C7—C6	−174.52 (18)

Symmetry code: (i) y−1, x+1, −z+2.

4,4'-Dimethylbenzophenone (3b)

Crystal data

C15H14O	F(000) = 448
Mr = 210.26	Dx = 1.207 Mg m^−3
Orthorhombic, P212121	Ag Kα radiation, λ = 0.56086 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5696 reflections
a = 12.1952 (10) Å	θ = 2.4–23.6°
b = 7.8601 (7) Å	µ = 0.05 mm^−1
c = 12.0734 (12) Å	T = 173 K
V = 1157.30 (18) Å^3	Block, colourless
Z = 4	0.35 × 0.3 × 0.15 mm

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	3195 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 23.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→17
Tmin = 0.9, Tmax = 0.95	k = −11→11
11865 measured reflections	l = −17→17
3526 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0751P)^2 + 0.189P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.130	(Δ/σ)max < 0.001
S = 1.08	Δρmax = 0.31 e Å^−3
3526 reflections	Δρmin = −0.22 e Å^−3
147 parameters	Absolute structure: Flack x determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.2 (9)
0 constraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1	0.73834 (14)	0.1922 (3)	0.67393 (15)	0.0255 (4)
C2	0.65061 (13)	0.1956 (2)	0.75991 (14)	0.0215 (3)
C3	0.66678 (15)	0.1019 (2)	0.85730 (15)	0.0241 (3)
H3	0.731634	0.036309	0.865954	0.029*
C4	0.58906 (15)	0.1040 (2)	0.94123 (15)	0.0257 (4)
H4	0.60087	0.038548	1.006283	0.031*
C5	0.49340 (14)	0.2015 (2)	0.93123 (15)	0.0247 (3)
C6	0.47804 (14)	0.2946 (2)	0.83413 (15)	0.0249 (3)
H6	0.413437	0.360902	0.825807	0.03*
C7	0.55499 (14)	0.2926 (2)	0.74923 (15)	0.0235 (3)
H7	0.54267	0.357171	0.683894	0.028*
C8	0.71343 (14)	0.2369 (2)	0.55603 (15)	0.0235 (3)
C9	0.79480 (14)	0.3159 (2)	0.49309 (16)	0.0260 (4)
H9	0.862984	0.343812	0.526513	0.031*
C10	0.77739 (16)	0.3541 (3)	0.38259 (17)	0.0286 (4)
H10	0.833214	0.410142	0.341604	0.034*
C11	0.67945 (15)	0.3116 (2)	0.33071 (15)	0.0274 (4)
C12	0.59824 (15)	0.2306 (3)	0.39300 (16)	0.0275 (4)
H12	0.530983	0.199985	0.358676	0.033*
C13	0.61441 (14)	0.1943 (3)	0.50447 (15)	0.0257 (4)
H13	0.558011	0.140248	0.545815	0.031*
C14	0.40933 (17)	0.2048 (3)	1.02228 (19)	0.0362 (4)
H14A	0.401301	0.321366	1.049937	0.054*
H14B	0.433111	0.130405	1.082825	0.054*
H14C	0.338786	0.164797	0.993435	0.054*
C15	0.6606 (2)	0.3508 (4)	0.21003 (18)	0.0442 (6)
H15A	0.725924	0.406026	0.179271	0.066*
H15B	0.597455	0.426994	0.2026	0.066*
H15C	0.64628	0.244874	0.16974	0.066*
O1	0.83208 (12)	0.1531 (3)	0.69919 (13)	0.0438 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0201 (7)	0.0328 (9)	0.0235 (8)	0.0001 (7)	−0.0006 (6)	0.0015 (7)
C2	0.0198 (7)	0.0235 (7)	0.0213 (7)	−0.0008 (6)	−0.0011 (5)	−0.0011 (7)
C3	0.0233 (7)	0.0247 (8)	0.0242 (8)	0.0028 (6)	−0.0045 (6)	−0.0010 (7)
C4	0.0295 (8)	0.0252 (8)	0.0224 (7)	−0.0007 (7)	−0.0028 (6)	0.0004 (7)
C5	0.0261 (8)	0.0221 (8)	0.0259 (8)	−0.0027 (6)	0.0030 (6)	−0.0029 (7)
C6	0.0231 (7)	0.0219 (7)	0.0298 (9)	0.0027 (6)	0.0005 (6)	−0.0011 (7)
C7	0.0239 (7)	0.0229 (8)	0.0238 (8)	0.0025 (6)	−0.0009 (6)	0.0022 (7)
C8	0.0196 (7)	0.0278 (8)	0.0230 (7)	0.0013 (6)	0.0015 (6)	−0.0004 (7)
C9	0.0187 (7)	0.0311 (9)	0.0282 (9)	−0.0018 (7)	0.0033 (6)	−0.0031 (7)
C10	0.0282 (9)	0.0296 (9)	0.0281 (9)	−0.0014 (7)	0.0084 (7)	0.0012 (7)
C11	0.0308 (9)	0.0282 (9)	0.0231 (8)	0.0040 (7)	0.0027 (6)	0.0008 (7)
C12	0.0231 (8)	0.0341 (10)	0.0255 (8)	0.0004 (7)	−0.0020 (6)	−0.0007 (7)
C13	0.0207 (7)	0.0307 (9)	0.0257 (8)	−0.0019 (7)	0.0008 (6)	0.0019 (7)
C14	0.0351 (10)	0.0382 (11)	0.0353 (10)	−0.0009 (9)	0.0124 (8)	−0.0004 (9)
C15	0.0495 (13)	0.0582 (15)	0.0248 (9)	0.0018 (11)	−0.0004 (9)	0.0079 (10)
O1	0.0216 (6)	0.0751 (13)	0.0346 (8)	0.0099 (7)	−0.0022 (6)	0.0085 (8)

Geometric parameters (Å, º)

C1—O1	1.222 (2)	C9—C10	1.384 (3)
C1—C2	1.491 (2)	C9—H9	0.95
C1—C8	1.497 (3)	C10—C11	1.389 (3)
C2—C7	1.399 (2)	C10—H10	0.95
C2—C3	1.401 (2)	C11—C12	1.397 (3)
C3—C4	1.388 (3)	C11—C15	1.507 (3)
C3—H3	0.95	C12—C13	1.390 (3)
C4—C5	1.401 (3)	C12—H12	0.95
C4—H4	0.95	C13—H13	0.95
C5—C6	1.395 (3)	C14—H14A	0.98
C5—C14	1.503 (3)	C14—H14B	0.98
C6—C7	1.390 (2)	C14—H14C	0.98
C6—H6	0.95	C15—H15A	0.98
C7—H7	0.95	C15—H15B	0.98
C8—C9	1.396 (2)	C15—H15C	0.98
C8—C13	1.399 (2)
O1—C1—C2	120.13 (17)	C8—C9—H9	119.6
O1—C1—C8	119.08 (17)	C9—C10—C11	120.95 (17)
C2—C1—C8	120.80 (14)	C9—C10—H10	119.5
C7—C2—C3	118.75 (16)	C11—C10—H10	119.5
C7—C2—C1	122.93 (16)	C10—C11—C12	118.45 (17)
C3—C2—C1	118.28 (15)	C10—C11—C15	121.17 (19)
C4—C3—C2	120.69 (16)	C12—C11—C15	120.38 (19)
C4—C3—H3	119.7	C13—C12—C11	120.96 (18)
C2—C3—H3	119.7	C13—C12—H12	119.5
C3—C4—C5	120.82 (17)	C11—C12—H12	119.5
C3—C4—H4	119.6	C12—C13—C8	120.26 (17)
C5—C4—H4	119.6	C12—C13—H13	119.9
C6—C5—C4	118.11 (16)	C8—C13—H13	119.9
C6—C5—C14	120.94 (17)	C5—C14—H14A	109.5
C4—C5—C14	120.95 (18)	C5—C14—H14B	109.5
C7—C6—C5	121.56 (16)	H14A—C14—H14B	109.5
C7—C6—H6	119.2	C5—C14—H14C	109.5
C5—C6—H6	119.2	H14A—C14—H14C	109.5
C6—C7—C2	120.06 (16)	H14B—C14—H14C	109.5
C6—C7—H7	120	C11—C15—H15A	109.5
C2—C7—H7	120	C11—C15—H15B	109.5
C9—C8—C13	118.55 (17)	H15A—C15—H15B	109.5
C9—C8—C1	118.55 (16)	C11—C15—H15C	109.5
C13—C8—C1	122.80 (16)	H15A—C15—H15C	109.5
C10—C9—C8	120.82 (17)	H15B—C15—H15C	109.5
C10—C9—H9	119.6
O1—C1—C2—C7	156.6 (2)	O1—C1—C8—C9	−32.2 (3)
C8—C1—C2—C7	−23.1 (3)	C2—C1—C8—C9	147.54 (18)
O1—C1—C2—C3	−21.1 (3)	O1—C1—C8—C13	144.0 (2)
C8—C1—C2—C3	159.20 (17)	C2—C1—C8—C13	−36.2 (3)
C7—C2—C3—C4	0.6 (3)	C13—C8—C9—C10	1.1 (3)
C1—C2—C3—C4	178.36 (17)	C1—C8—C9—C10	177.54 (17)
C2—C3—C4—C5	−0.9 (3)	C8—C9—C10—C11	−1.4 (3)
C3—C4—C5—C6	0.7 (3)	C9—C10—C11—C12	0.6 (3)
C3—C4—C5—C14	−179.67 (18)	C9—C10—C11—C15	−179.2 (2)
C4—C5—C6—C7	−0.3 (3)	C10—C11—C12—C13	0.4 (3)
C14—C5—C6—C7	−179.93 (18)	C15—C11—C12—C13	−179.8 (2)
C5—C6—C7—C2	0.1 (3)	C11—C12—C13—C8	−0.7 (3)
C3—C2—C7—C6	−0.2 (3)	C9—C8—C13—C12	−0.1 (3)
C1—C2—C7—C6	−177.85 (17)	C1—C8—C13—C12	−176.35 (18)

4,4'-Dimethylbenzophenone (3c)

Crystal data

C15H14O	F(000) = 896
Mr = 210.26	Dx = 1.208 Mg m^−3
Monoclinic, P21/c	Ag Kα radiation, λ = 0.56086 Å
Hall symbol: -P 2ybc	Cell parameters from 9909 reflections
a = 25.369 (3) Å	θ = 2.7–23.7°
b = 6.0310 (7) Å	µ = 0.05 mm^−1
c = 15.256 (2) Å	T = 173 K
β = 97.788 (4)°	Block, colourless
V = 2312.8 (5) Å^3	0.35 × 0.25 × 0.24 mm
Z = 8

Data collection

Bruker D8 Venture Photon CCD area detector diffractometer	5503 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 23.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −36→36
Tmin = 0.95, Tmax = 0.96	k = −8→8
33620 measured reflections	l = −21→21
7106 independent reflections

Refinement

Refinement on F^2	0 constraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.053	H-atom parameters constrained
wR(F^2) = 0.162	w = 1/[σ^2(Fo^2) + (0.0762P)^2 + 0.9672P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
7106 reflections	Δρmax = 0.39 e Å^−3
293 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

Experimental. Absorption corrections were made using the program SADABS (Sheldrick, 1996)

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
C1A	0.10858 (5)	0.2697 (2)	0.37147 (10)	0.0293 (3)
C2A	0.05796 (5)	0.3939 (2)	0.37342 (8)	0.0240 (2)
C3A	0.00998 (5)	0.2921 (2)	0.33854 (9)	0.0294 (3)
H3A	0.010348	0.148606	0.31296	0.035*
C4A	−0.03784 (5)	0.3998 (3)	0.34125 (9)	0.0326 (3)
H4A	−0.070023	0.329658	0.316759	0.039*
C5A	−0.03982 (5)	0.6092 (2)	0.37916 (9)	0.0305 (3)
C6A	0.00779 (5)	0.7074 (2)	0.41506 (9)	0.0290 (3)
H6A	0.007179	0.848844	0.44233	0.035*
C7A	0.05621 (5)	0.6029 (2)	0.41184 (9)	0.0253 (2)
H7A	0.088327	0.674204	0.435933	0.03*
C8A	0.15969 (5)	0.38804 (19)	0.36441 (8)	0.0235 (2)
C9A	0.20765 (5)	0.2772 (2)	0.39171 (9)	0.0281 (3)
H9A	0.207019	0.133592	0.417124	0.034*
C10A	0.25597 (5)	0.3747 (2)	0.38207 (9)	0.0295 (3)
H10A	0.288086	0.297441	0.401289	0.035*
C11A	0.25809 (5)	0.5844 (2)	0.34459 (9)	0.0278 (3)
C12A	0.21038 (5)	0.6952 (2)	0.31818 (9)	0.0270 (3)
H12A	0.21117	0.839184	0.293102	0.032*
C13A	0.16169 (5)	0.5994 (2)	0.32778 (8)	0.0244 (2)
H13A	0.129656	0.67805	0.30935	0.029*
C14A	−0.09205 (6)	0.7279 (3)	0.38060 (13)	0.0469 (4)
H14A	−0.08571	0.869089	0.412087	0.07*
H14B	−0.115758	0.635567	0.410847	0.07*
H14C	−0.108593	0.756269	0.319795	0.07*
C15A	0.31058 (6)	0.6883 (3)	0.33221 (11)	0.0397 (3)
H15A	0.339067	0.620221	0.373251	0.06*
H15B	0.309305	0.847796	0.344061	0.06*
H15C	0.317509	0.664539	0.271261	0.06*
O1A	0.10840 (5)	0.06755 (18)	0.37508 (11)	0.0557 (4)
C1B	0.37577 (5)	0.1595 (2)	0.10226 (9)	0.0303 (3)
C2B	0.32925 (5)	0.3111 (2)	0.10270 (8)	0.0260 (2)
C3B	0.32740 (5)	0.5074 (2)	0.05432 (9)	0.0311 (3)
H3B	0.356494	0.547515	0.024434	0.037*
C4B	0.28326 (6)	0.6442 (2)	0.04964 (9)	0.0327 (3)
H4B	0.283124	0.781058	0.018765	0.039*
C5B	0.23900 (5)	0.5844 (2)	0.08953 (9)	0.0295 (3)
C6B	0.24106 (5)	0.3874 (2)	0.13747 (9)	0.0281 (3)
H6B	0.211278	0.343955	0.165045	0.034*
C7B	0.28594 (5)	0.2538 (2)	0.14557 (9)	0.0270 (3)
H7B	0.287223	0.122794	0.180401	0.032*
C8B	0.39987 (5)	0.0540 (2)	0.18611 (8)	0.0261 (3)
C9B	0.42823 (5)	−0.1441 (2)	0.18335 (10)	0.0314 (3)
H9B	0.431673	−0.210438	0.127941	0.038*
C10B	0.45132 (5)	−0.2440 (2)	0.26073 (10)	0.0336 (3)
H10B	0.46984	−0.380202	0.257909	0.04*
C11B	0.44779 (5)	−0.1480 (2)	0.34262 (10)	0.0318 (3)
C12B	0.42123 (5)	0.0536 (2)	0.34514 (9)	0.0306 (3)
H12B	0.419718	0.124282	0.400392	0.037*
C13B	0.39691 (5)	0.1525 (2)	0.26786 (9)	0.0278 (3)
H13B	0.37816	0.288069	0.270788	0.033*
C14B	0.18979 (7)	0.7271 (3)	0.07828 (11)	0.0439 (4)
H14D	0.16674	0.68351	0.024223	0.066*
H14E	0.19999	0.883025	0.073926	0.066*
H14F	0.170627	0.707549	0.129366	0.066*
C15B	0.47112 (7)	−0.2626 (3)	0.42639 (12)	0.0483 (4)
H15D	0.449708	−0.3935	0.435817	0.072*
H15E	0.471185	−0.16068	0.47644	0.072*
H15F	0.507681	−0.308309	0.421561	0.072*
O1B	0.39347 (5)	0.1240 (2)	0.03285 (7)	0.0491 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0324 (6)	0.0175 (5)	0.0391 (7)	−0.0017 (5)	0.0092 (5)	−0.0004 (5)
C2A	0.0277 (6)	0.0189 (5)	0.0259 (6)	−0.0023 (4)	0.0059 (4)	0.0004 (4)
C3A	0.0353 (7)	0.0256 (6)	0.0277 (6)	−0.0090 (5)	0.0057 (5)	−0.0045 (5)
C4A	0.0285 (6)	0.0399 (7)	0.0289 (6)	−0.0083 (5)	0.0018 (5)	0.0006 (5)
C5A	0.0292 (6)	0.0352 (7)	0.0280 (6)	0.0028 (5)	0.0073 (5)	0.0088 (5)
C6A	0.0351 (7)	0.0229 (6)	0.0304 (6)	0.0019 (5)	0.0093 (5)	0.0006 (5)
C7A	0.0272 (6)	0.0204 (5)	0.0286 (6)	−0.0032 (4)	0.0044 (5)	−0.0017 (4)
C8A	0.0274 (6)	0.0182 (5)	0.0253 (6)	0.0005 (4)	0.0048 (4)	−0.0010 (4)
C9A	0.0340 (6)	0.0215 (5)	0.0286 (6)	0.0048 (5)	0.0038 (5)	0.0025 (5)
C10A	0.0276 (6)	0.0315 (6)	0.0285 (6)	0.0059 (5)	0.0004 (5)	−0.0024 (5)
C11A	0.0279 (6)	0.0315 (6)	0.0247 (6)	−0.0037 (5)	0.0051 (5)	−0.0066 (5)
C12A	0.0325 (6)	0.0215 (5)	0.0275 (6)	−0.0021 (5)	0.0064 (5)	0.0007 (5)
C13A	0.0266 (5)	0.0202 (5)	0.0262 (6)	0.0013 (4)	0.0030 (4)	0.0008 (4)
C14A	0.0333 (7)	0.0557 (10)	0.0530 (10)	0.0120 (7)	0.0110 (7)	0.0131 (8)
C15A	0.0311 (7)	0.0471 (9)	0.0426 (8)	−0.0088 (6)	0.0104 (6)	−0.0079 (7)
O1A	0.0442 (6)	0.0167 (5)	0.1095 (12)	−0.0011 (4)	0.0223 (7)	0.0012 (6)
C1B	0.0258 (6)	0.0407 (7)	0.0250 (6)	0.0031 (5)	0.0053 (5)	0.0007 (5)
C2B	0.0233 (5)	0.0335 (6)	0.0210 (5)	0.0014 (5)	0.0023 (4)	0.0010 (5)
C3B	0.0302 (6)	0.0396 (7)	0.0237 (6)	−0.0042 (5)	0.0040 (5)	0.0044 (5)
C4B	0.0394 (7)	0.0316 (7)	0.0257 (6)	0.0004 (6)	−0.0002 (5)	0.0063 (5)
C5B	0.0302 (6)	0.0331 (7)	0.0234 (6)	0.0045 (5)	−0.0030 (5)	−0.0020 (5)
C6B	0.0238 (5)	0.0333 (7)	0.0271 (6)	−0.0004 (5)	0.0032 (4)	−0.0004 (5)
C7B	0.0260 (6)	0.0287 (6)	0.0264 (6)	0.0004 (5)	0.0039 (5)	0.0030 (5)
C8B	0.0215 (5)	0.0318 (6)	0.0253 (6)	0.0013 (5)	0.0047 (4)	0.0005 (5)
C9B	0.0267 (6)	0.0344 (7)	0.0336 (7)	0.0029 (5)	0.0058 (5)	−0.0047 (5)
C10B	0.0258 (6)	0.0289 (6)	0.0463 (8)	0.0028 (5)	0.0058 (5)	0.0038 (6)
C11B	0.0212 (5)	0.0379 (7)	0.0362 (7)	−0.0025 (5)	0.0035 (5)	0.0118 (6)
C12B	0.0273 (6)	0.0394 (7)	0.0254 (6)	−0.0011 (5)	0.0047 (5)	0.0022 (5)
C13B	0.0256 (6)	0.0305 (6)	0.0278 (6)	0.0025 (5)	0.0052 (5)	0.0006 (5)
C14B	0.0428 (8)	0.0470 (9)	0.0399 (8)	0.0181 (7)	−0.0017 (6)	0.0036 (7)
C15B	0.0388 (8)	0.0602 (11)	0.0447 (9)	0.0030 (8)	0.0013 (7)	0.0243 (8)
O1B	0.0438 (6)	0.0777 (9)	0.0282 (5)	0.0201 (6)	0.0134 (5)	0.0041 (5)

Geometric parameters (Å, º)

C1A—O1A	1.2205 (16)	C1B—O1B	1.2239 (17)
C1A—C2A	1.4905 (18)	C1B—C8B	1.4843 (18)
C1A—C8A	1.4966 (18)	C1B—C2B	1.4935 (18)
C2A—C7A	1.3937 (17)	C2B—C3B	1.3924 (19)
C2A—C3A	1.4020 (17)	C2B—C7B	1.3961 (18)
C3A—C4A	1.382 (2)	C3B—C4B	1.385 (2)
C3A—H3A	0.95	C3B—H3B	0.95
C4A—C5A	1.393 (2)	C4B—C5B	1.395 (2)
C4A—H4A	0.95	C4B—H4B	0.95
C5A—C6A	1.3894 (19)	C5B—C6B	1.3925 (19)
C5A—C14A	1.509 (2)	C5B—C14B	1.5067 (19)
C6A—C7A	1.3874 (18)	C6B—C7B	1.3871 (18)
C6A—H6A	0.95	C6B—H6B	0.95
C7A—H7A	0.95	C7B—H7B	0.95
C8A—C13A	1.3956 (17)	C8B—C13B	1.3925 (18)
C8A—C9A	1.4011 (17)	C8B—C9B	1.3983 (19)
C9A—C10A	1.3854 (19)	C9B—C10B	1.383 (2)
C9A—H9A	0.95	C9B—H9B	0.95
C10A—C11A	1.392 (2)	C10B—C11B	1.391 (2)
C10A—H10A	0.95	C10B—H10B	0.95
C11A—C12A	1.3936 (18)	C11B—C12B	1.393 (2)
C11A—C15A	1.5065 (19)	C11B—C15B	1.502 (2)
C12A—C13A	1.3894 (17)	C12B—C13B	1.3890 (18)
C12A—H12A	0.95	C12B—H12B	0.95
C13A—H13A	0.95	C13B—H13B	0.95
C14A—H14A	0.98	C14B—H14D	0.98
C14A—H14B	0.98	C14B—H14E	0.98
C14A—H14C	0.98	C14B—H14F	0.98
C15A—H15A	0.98	C15B—H15D	0.98
C15A—H15B	0.98	C15B—H15E	0.98
C15A—H15C	0.98	C15B—H15F	0.98
O1A—C1A—C2A	119.50 (12)	O1B—C1B—C8B	120.94 (13)
O1A—C1A—C8A	119.22 (12)	O1B—C1B—C2B	119.59 (12)
C2A—C1A—C8A	121.28 (11)	C8B—C1B—C2B	119.47 (11)
C7A—C2A—C3A	118.70 (12)	C3B—C2B—C7B	119.13 (12)
C7A—C2A—C1A	122.64 (11)	C3B—C2B—C1B	119.20 (12)
C3A—C2A—C1A	118.60 (11)	C7B—C2B—C1B	121.53 (12)
C4A—C3A—C2A	120.23 (12)	C4B—C3B—C2B	120.18 (13)
C4A—C3A—H3A	119.9	C4B—C3B—H3B	119.9
C2A—C3A—H3A	119.9	C2B—C3B—H3B	119.9
C3A—C4A—C5A	121.32 (12)	C3B—C4B—C5B	121.09 (13)
C3A—C4A—H4A	119.3	C3B—C4B—H4B	119.5
C5A—C4A—H4A	119.3	C5B—C4B—H4B	119.5
C6A—C5A—C4A	118.17 (13)	C6B—C5B—C4B	118.33 (12)
C6A—C5A—C14A	120.67 (14)	C6B—C5B—C14B	121.24 (14)
C4A—C5A—C14A	121.16 (14)	C4B—C5B—C14B	120.41 (13)
C7A—C6A—C5A	121.26 (13)	C7B—C6B—C5B	120.97 (12)
C7A—C6A—H6A	119.4	C7B—C6B—H6B	119.5
C5A—C6A—H6A	119.4	C5B—C6B—H6B	119.5
C6A—C7A—C2A	120.30 (12)	C6B—C7B—C2B	120.20 (12)
C6A—C7A—H7A	119.8	C6B—C7B—H7B	119.9
C2A—C7A—H7A	119.8	C2B—C7B—H7B	119.9
C13A—C8A—C9A	118.53 (12)	C13B—C8B—C9B	118.80 (12)
C13A—C8A—C1A	122.90 (11)	C13B—C8B—C1B	121.55 (12)
C9A—C8A—C1A	118.49 (11)	C9B—C8B—C1B	119.60 (12)
C10A—C9A—C8A	120.74 (12)	C10B—C9B—C8B	120.46 (13)
C10A—C9A—H9A	119.6	C10B—C9B—H9B	119.8
C8A—C9A—H9A	119.6	C8B—C9B—H9B	119.8
C9A—C10A—C11A	120.90 (12)	C9B—C10B—C11B	120.92 (13)
C9A—C10A—H10A	119.6	C9B—C10B—H10B	119.5
C11A—C10A—H10A	119.6	C11B—C10B—H10B	119.5
C10A—C11A—C12A	118.30 (12)	C10B—C11B—C12B	118.58 (13)
C10A—C11A—C15A	120.90 (13)	C10B—C11B—C15B	120.45 (15)
C12A—C11A—C15A	120.79 (13)	C12B—C11B—C15B	120.96 (15)
C13A—C12A—C11A	121.32 (12)	C13B—C12B—C11B	120.81 (13)
C13A—C12A—H12A	119.3	C13B—C12B—H12B	119.6
C11A—C12A—H12A	119.3	C11B—C12B—H12B	119.6
C12A—C13A—C8A	120.21 (11)	C12B—C13B—C8B	120.36 (13)
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.8
C8A—C13A—H13A	119.9	C8B—C13B—H13B	119.8
C5A—C14A—H14A	109.5	C5B—C14B—H14D	109.5
C5A—C14A—H14B	109.5	C5B—C14B—H14E	109.5
H14A—C14A—H14B	109.5	H14D—C14B—H14E	109.5
C5A—C14A—H14C	109.5	C5B—C14B—H14F	109.5
H14A—C14A—H14C	109.5	H14D—C14B—H14F	109.5
H14B—C14A—H14C	109.5	H14E—C14B—H14F	109.5
C11A—C15A—H15A	109.5	C11B—C15B—H15D	109.5
C11A—C15A—H15B	109.5	C11B—C15B—H15E	109.5
H15A—C15A—H15B	109.5	H15D—C15B—H15E	109.5
C11A—C15A—H15C	109.5	C11B—C15B—H15F	109.5
H15A—C15A—H15C	109.5	H15D—C15B—H15F	109.5
H15B—C15A—H15C	109.5	H15E—C15B—H15F	109.5
O1A—C1A—C2A—C7A	147.58 (15)	O1B—C1B—C2B—C3B	−42.4 (2)
C8A—C1A—C2A—C7A	−32.93 (19)	C8B—C1B—C2B—C3B	137.64 (13)
O1A—C1A—C2A—C3A	−29.6 (2)	O1B—C1B—C2B—C7B	133.29 (16)
C8A—C1A—C2A—C3A	149.86 (13)	C8B—C1B—C2B—C7B	−46.71 (18)
C7A—C2A—C3A—C4A	1.0 (2)	C7B—C2B—C3B—C4B	0.5 (2)
C1A—C2A—C3A—C4A	178.35 (12)	C1B—C2B—C3B—C4B	176.30 (12)
C2A—C3A—C4A—C5A	−0.7 (2)	C2B—C3B—C4B—C5B	−2.9 (2)
C3A—C4A—C5A—C6A	−0.4 (2)	C3B—C4B—C5B—C6B	2.6 (2)
C3A—C4A—C5A—C14A	178.95 (14)	C3B—C4B—C5B—C14B	−175.56 (13)
C4A—C5A—C6A—C7A	1.3 (2)	C4B—C5B—C6B—C7B	0.1 (2)
C14A—C5A—C6A—C7A	−178.07 (13)	C14B—C5B—C6B—C7B	178.22 (13)
C5A—C6A—C7A—C2A	−1.0 (2)	C5B—C6B—C7B—C2B	−2.4 (2)
C3A—C2A—C7A—C6A	−0.15 (19)	C3B—C2B—C7B—C6B	2.10 (19)
C1A—C2A—C7A—C6A	−177.36 (12)	C1B—C2B—C7B—C6B	−173.55 (12)
O1A—C1A—C8A—C13A	155.35 (15)	O1B—C1B—C8B—C13B	152.98 (15)
C2A—C1A—C8A—C13A	−24.15 (19)	C2B—C1B—C8B—C13B	−27.02 (19)
O1A—C1A—C8A—C9A	−21.4 (2)	O1B—C1B—C8B—C9B	−24.2 (2)
C2A—C1A—C8A—C9A	159.15 (13)	C2B—C1B—C8B—C9B	155.76 (13)
C13A—C8A—C9A—C10A	−0.39 (19)	C13B—C8B—C9B—C10B	2.2 (2)
C1A—C8A—C9A—C10A	176.46 (12)	C1B—C8B—C9B—C10B	179.52 (12)
C8A—C9A—C10A—C11A	−0.4 (2)	C8B—C9B—C10B—C11B	−1.3 (2)
C9A—C10A—C11A—C12A	0.92 (19)	C9B—C10B—C11B—C12B	−1.1 (2)
C9A—C10A—C11A—C15A	−178.61 (13)	C9B—C10B—C11B—C15B	177.53 (13)
C10A—C11A—C12A—C13A	−0.71 (19)	C10B—C11B—C12B—C13B	2.5 (2)
C15A—C11A—C12A—C13A	178.81 (12)	C15B—C11B—C12B—C13B	−176.06 (13)
C11A—C12A—C13A—C8A	−0.04 (19)	C11B—C12B—C13B—C8B	−1.6 (2)
C9A—C8A—C13A—C12A	0.60 (19)	C9B—C8B—C13B—C12B	−0.77 (19)
C1A—C8A—C13A—C12A	−176.11 (12)	C1B—C8B—C13B—C12B	−178.01 (12)