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.
Supporting information
CCDC references: 1040499; 1040498; 1040497; 1040496; 1040495
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)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 16 | 0.5 × 0.4 × 0.3 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.4555P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0013 (2) |
0 constraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H2A···O1Ai | 0.93 (2) | 1.75 (3) | 2.6707 (18) | 170 (2) |
O2B—H2B···O1Bii | 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)
top
Crystal data top
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) Å3 | Plate, yellow |
Z = 8 | 0.39 × 0.37 × 0.03 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0356P)2 + 0.4214P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C14B—H14E···O1Ai | 0.98 | 2.48 | 3.448 (2) | 168 |
Symmetry code: (i) x−1/2, −y+3/2, −z+2. |
4,4'-Dimethylbenzophenone (3a)
top
Crystal data top
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) Å3 | Plate, colourless |
Z = 3 | 0.43 × 0.17 × 0.05 mm |
F(000) = 336 | |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0484P)2 + 0.1427P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
C1—O1 | 1.222 (4) | C5—C6 | 1.392 (3) |
C1—C2i | 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—C2i | 119.9 (3) | C6—C5—C8 | 120.7 (2) |
O1—C1—C2 | 119.9 (3) | C7—C6—C5 | 121.2 (2) |
C2i—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) |
C2i—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) |
C2i—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)
top
Crystal data top
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) Å3 | Block, colourless |
Z = 4 | 0.35 × 0.3 × 0.15 mm |
Data collection top
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 top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.044 | w = 1/[σ2(Fo2) + (0.0751P)2 + 0.189P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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)
top
Crystal data top
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) Å3 | 0.35 × 0.25 × 0.24 mm |
Z = 8 | |
Data collection top
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 top
Refinement on F2 | 0 constraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.162 | w = 1/[σ2(Fo2) + (0.0762P)2 + 0.9672P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) |
Comparison of geometric descriptors and lattice energies for polymorphs
(1a)–(3c) reported in this study topCompound | 4-Hydroxybenzophenone | | 4-(Dimethylamino)benzophenone | | 4,4'-Dimethylbenzophenone | | |
Polymorph | (1a) | (1b) | (2a) | (2b) | (3a) | (3b) | (3c) |
τ1a (°) | 11.9 (2) | -11.9 (1) | 25.7 (3) | -10.8 (1) | 28.2 (2) | -21.1 (3) | -29.6 (2) |
| -10.6 (2) | -11.4 (1) | -20.8 (3) | | | | -42.4 (2) |
τ2b (°) | 38.5 (2) | -37.4 (1) | 32.7 (3) | -35.1 (1) | 28.2 (2) | -32.3 (3) | -21.4 (2) |
| -39.0 (2) | 37.6 (1) | -32.0 (2) | | | | -24.2 (2) |
CCDC | 1040495 | YAJPUV | 1040496 | KOFHET | 1040497 | 1040498 | 1040499 |
Elatt (kcal mol-1) | -65.1 | -66.3 | -71.0 | -72.3 | -63.9 | -63.9 | -62.8 |
Notes: (a) τ1 is defined as O1—C1—C2—C3;
(b τ2 is defined as O1—C1—C8—C9. |
Comparison of unit-cell parameters and lattice energies for the previously
reported polymorphs (4a)–(12b) topCompound | Benzophenone | | 4,4'-Diaminobenzophenone | | 4,4'-Dimethoxybenzophenone | | |
Polymorph | (4a) | (4b) | (5a) | (5b) | (6a) | (6b) | |
Crystal system | Monoclinic | Orthorhombic | Trigonal | Orthorhombic | Monoclinic | Orthorhombic | |
Space Group | C2/c | P212121 | P31 | P212121 | P21/a | P1 | |
a (Å) | 16.214 (3) | 7.738 | 9.136 (2) | 5.498 (0) | 16.430 | 9.430 (1) | |
b (Å) | 8.123 (1) | 10.242 | 9.136 (2) | 8.111 (0) | 16.030 | 9.457 (1) | |
c (Å) | 16.280 (3) | 12.040 | 10.953 (3) | 24.306 (2) | 9.620 | 14.796 (1) | |
α (°) | 90.00 | 90.00 | 90.00 | 90.00 | 90.00 | 76.95 (1) | |
β (°) | 112.78 (1) | 90.00 | 90.00 | 90.00 | 100.85 | 78.81 (1) | |
γ (°) | 90.00 | 90.00 | 120.00 | 90.00 | 90.00 | 70.67 (1) | |
V (Å3) | 1976.871 | 954.146 | 791.728 | 1083.948 | 2488.354 | 1202.648 | |
Z'/Z | 1/8 | 1/4 | 1/3 | 1/4 | 2/8 | 2/4 | |
Elatt (kcal mol-1) | -53.9 | -59.1 | -79.2 | -77.2 | -70.5 | -75.6 | |
CCDC | BPHENO11 | BPHENO12 | AMBZPH | AMBZPH02 | DMBOPN | DMBOPN01 | |
| | | | | | | |
Compound | 4-Methylbenzophenone | | 2-Amino-5-nitrobenzophenone | | | Hydroxyphenstatin | |
Polymorph | (7a) | (7b) | (8a) | (8b) | (8c) | (9a) | (9b) |
Crystal system | Monoclinic | Trigonal | Monoclinic | Monoclinic | Monoclinic | Monoclinic | Orthorhombic |
Space Group | P21/c | P31 | P21/c | P21/c | P21/c | Pc | Pbca |
a (Å) | 5.701 (1) | 9.217 (3) | 5.736 (1) | 7.701 (2) | 7.724 (1) | 10.423 (2) | 10.807 (2) |
b (Å) | 13.890 (1) | 9.217 (3) | 14.693 (2) | 11.120 (2) | 19.298 (1) | 11.297 (2) | 14.630 (3) |
c (Å) | 14.077 (2) | 11.294 (2) | 13.112 (1) | 12.707 (1) | 7.658 (1) | 14.173 (3) | 19.876 (4) |
α (°) | 90.00 | 90 | 90.00 | 90.00 | 90.00 | 90.00 | 90.00 |
β (°) | 95.18 (2) | 90 | 98.87 (4) | 96.75 (1) | 95.94 (1) | 111.02 (3) | 90.00 |
γ (°) | 90.00 | 120 | 90.00 | 90.00 | 90.00 | 90.00 | 90.00 |
V (Å3) | 1110.161 | 830.917 | 1091.813 | 1080.591 | 1135.255 | 1557.798 | 3142.523 |
Z'/Z | 1/4 | 1/3 | 1/4 | 1/4 | 1/4 | 2/4 | 1/8 |
Elatt (kcal mol-1) | -56.2 | -56.7 | -73.5 | -76.1 | -69.5 | -87.7 | -88.9 |
CCDC | FEVNAV01 | FEFNAV02 | DUDZIL01 | DUDZIL02 | DUDZIL03 | UBEDUA | UBEDUA01 |
| | | | | | | |
Compound | Bis(4-nitrophenyl) ketone | | 4-Bromobenzophenone | | 3,3'-Dinitrobenzophenone | | |
Polymorph | (10a) | (10b) | (11a) | (11b) | (12a) | (12b) | |
Crystal system | Triclinic | Orthorhombic | Monoclinic | Triclinic | Monoclinic | Orthorhombic | |
Space Group | P1 | Fdd2 | P21/c | P1 | P212121 | P1 | |
a (Å) | 7.323 (2) | 12.822 (1) | 12.124 (1) | 6.106 (1) | 18.94 (2) | 7.509 (4) | |
b (Å) | 12.634 (4) | 31.074 (1) | 14.646 (3) | 7.293 (1) | 5.029 (6) | 7.967 (5) | |
c (Å) | 13.301 (3) | 6.075 (1) | 6.159 (1) | 12.100 (1) | 6.071 (8) | 10.623 (8) | |
α (°) | 89.37 (2) | 90 | 90 | 98.20 (1) | 90 | 75.53 (3) | |
β (°) | 86.75 (2) | 90 | 97.38 (3) | 98.73 (1) | 90 | 83.95 (5) | |
γ (°) | 87.09 (3) | 90 | 90 | 91.11 (1) | 90 | 10.623 (8) | |
V (Å3) | 1226.988 | 2420.557 | 1084.494 | 526.639 | 578.258 | 575.150 | |
Z'/Z | 1/2 | 0.5/8 | 1/4 | 1/2 | 0.5/2 | 1/2 | |
Elatt (kcal mol-1) | -65.8 | -67.3 | -39.2 | -40.3 | -74.4 | -76.2 | |
CCDC | NOPHKN | NOPHKN01 | PIQLIK01 | PIQLIK03 | QUNDIO | QUNDIO01 | |