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Benzophenone was the first organic molecular material to be identified as polymorphic. It is well known that benzophenone crystallizes in a stable orthorhombic α-form (m.p. 321 K) with space group P212121 and a = 10.28, b = 12.12, c = 7.99 Å, [Girdwood (1998). Ph.D. thesis. Strathclyde University, Glasgow, Scotland]. Here we report two separate structure determinations of the metastable β-form (m.p. 297–299 K). Crystalline material of the metastable polymorph was obtained from a melt supercooled to ∼243 K. The structure was determined from X-ray powder diffraction data by employing a novel, computational systematic search procedure to identify trial packing arrangements for subsequent refinement. Unit-cell and space-group information, determined from indexing the powder diffraction data, was used to define the search space. The structure was also determined from single-crystal diffraction data at room temperature and at 223 K. The metastable phase is monoclinic with space group C2/c and a = 16.22, b = 8.15, c = 16.33 Å, β = 112.91° (at 223 K). The structures derived from the individual techniques are qualitatively the same. They are compared both with each other and with the stable polymorph and other benzophenone derivatives.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768100000355/an0561sup1.cif
Contains datablocks global, MSBENZ2, 223K

sft

Structure factor file (SHELXL table format) https://doi.org/10.1107/S0108768100000355/an0561sup2.sft
Supplementary material

txt

Text file https://doi.org/10.1107/S0108768100000355/an0561sup3.txt
Supplementary material

txt

Text file https://doi.org/10.1107/S0108768100000355/an0561sup4.txt
Supplementary material

CCDC references: 145823; 145824

Computing details top

Program(s) used to refine structure: GSAS for MSBENZ2.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
(MSBENZ2) top
Crystal data top
C13H10Oβ = 112.911 (5)°
Mr = 182.22V = 1988.35 (13) Å3
Monoclinic, C2/cZ = 8
Hall symbol: -C 2ycDx = 1.218 Mg m3
a = 16.2219 (11) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.1468 (3) Å?, ? × ? × ? mm
c = 16.3340 (7) Å
Data collection top
2θmin = 11.26°, 2θmax = 59.96°, 2θstep = 0.02°
Refinement top
Rp = ?? data points
Rwp = ?23 parameters
Rexp = ?
χ2 = 8.644
Crystal data top
C13H10Oβ = 112.911 (5)°
Mr = 182.22V = 1988.35 (13) Å3
Monoclinic, C2/cZ = 8
a = 16.2219 (11) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.1468 (3) Å?, ? × ? × ? mm
c = 16.3340 (7) Å
Data collection top
2θmin = 11.26°, 2θmax = 59.96°, 2θstep = 0.02°
Refinement top
Rp = ?χ2 = 8.644
Rwp = ?? data points
Rexp = ?23 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3802 (6)0.151 (2)0.9751 (12)0.0*
C10.3784 (6)0.242 (2)0.9228 (5)0.0*
C20.4685 (7)0.3183 (11)0.9157 (5)0.0*
C30.5480 (8)0.2240 (13)0.9436 (8)0.0*
C40.6261 (8)0.2898 (18)0.9375 (7)0.0*
C50.6248 (9)0.4500 (18)0.9033 (5)0.0*
C60.5453 (10)0.5443 (16)0.8754 (9)0.0*
C70.4671 (9)0.4785 (14)0.8816 (8)0.0*
C80.2910 (8)0.2968 (11)0.8547 (7)0.0*
C90.2211 (7)0.3455 (16)0.8809 (7)0.0*
C100.1380 (8)0.3972 (16)0.8161 (6)0.0*
C110.1247 (7)0.4002 (15)0.7252 (7)0.0*
C120.1947 (7)0.3515 (18)0.6990 (7)0.0*
C130.2778 (7)0.2998 (16)0.7638 (7)0.0*
(223K) top
Crystal data top
C13H10Oβ = 112.82 (2)°
Mr = 182.22V = 1966.2 (7) Å3
Monoclinic, C2/cZ = 8
Hall symbol: -C 2ycDx = 1.231 Mg m3
a = 16.200 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 8.104 (1) Å × × mm
c = 16.248 (4) Å
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C13H10Oβ = 112.82 (2)°
Mr = 182.22V = 1966.2 (7) Å3
Monoclinic, C2/cZ = 8
a = 16.200 (4) ÅCu Kα radiation
b = 8.104 (1) Å × × mm
c = 16.248 (4) Å
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.37698 (8)0.1592 (2)0.97451 (8)0.0539 (6)
C10.3758 (1)0.2532 (2)0.9152 (1)0.0389 (8)
C20.4603 (1)0.3130 (2)0.9099 (1)0.0374 (8)
C30.5373 (1)0.2183 (2)0.9444 (1)0.0481 (10)
C40.6166 (1)0.2743 (3)0.9420 (1)0.0574 (11)
C50.6207 (1)0.4289 (3)0.9073 (1)0.0583 (12)
C60.5449 (1)0.5242 (3)0.8737 (1)0.0562 (11)
C70.4648 (1)0.4668 (2)0.8739 (1)0.0477 (10)
C80.2884 (1)0.3088 (2)0.8460 (1)0.0380 (9)
C90.2187 (1)0.3516 (2)0.8713 (1)0.0488 (10)
C100.1369 (1)0.3984 (3)0.8069 (2)0.0595 (12)
C110.1238 (1)0.3975 (2)0.7180 (2)0.0621 (12)
C120.1924 (1)0.3539 (2)0.6924 (1)0.0571 (11)
C130.2750 (1)0.3113 (2)0.7566 (1)0.0463 (9)
H30.533 (1)0.108 (2)0.967 (1)0.057 (5)
H40.667 (1)0.204 (3)0.963 (1)0.071 (6)
H50.680 (1)0.467 (2)0.908 (1)0.063 (5)
H60.548 (1)0.633 (2)0.850 (1)0.067 (5)
H70.412 (1)0.535 (2)0.850 (1)0.057 (5)
H90.230 (1)0.349 (2)0.935 (1)0.067 (6)
H100.092 (1)0.429 (2)0.827 (1)0.066 (5)
H110.064 (1)0.432 (3)0.672 (1)0.080 (6)
H120.185 (1)0.354 (2)0.630 (1)0.070 (6)
H130.324 (1)0.278 (2)0.739 (1)0.051 (5)

Experimental details

(MSBENZ2)(223K)
Crystal data
Chemical formulaC13H10OC13H10O
Mr182.22182.22
Crystal system, space groupMonoclinic, C2/cMonoclinic, C2/c
Temperature (K)??
a, b, c (Å)16.2219 (11), 8.1468 (3), 16.3340 (7)16.200 (4), 8.104 (1), 16.248 (4)
β (°) 112.911 (5) 112.82 (2)
V3)1988.35 (13)1966.2 (7)
Z88
Radiation typeCu Kα, λ = 1.54178 ÅCu Kα
µ (mm1)?
Specimen shape, size (mm)?, ? × ? × ? × ×
Data collection
Diffractometer??
Specimen mounting?
Data collection mode?
Data collection method??
Absorption correction?
No. of measured, independent and
observed reflections
?, ?, ?
Rint?
θ values (°)2θmin = 11.26 2θmax = 59.96 2θstep = 0.02θmax = ?
Refinement
R factors and goodness of fitRp = ?, Rwp = ?, Rexp = ?, χ2 = 8.644R[F2 > 2σ(F2)] = ?, wR(F2) = ?, S = ?
No. of reflections/data points??
No. of parameters23?
No. of restraints??
Δρmax, Δρmin (e Å3)?, ?

Computer programs: GSAS.

 

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