Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
Crystals of cyclo­penta­none, C5H8O, and cyclo­butanone, C4H6O, have been grown in situ on a diffractometer. The two compounds are isostructural and contain two crystallographically independent mol­ecules. Mol­ecules sitting across twofold axes form anti­parallel dipole–dipole dimers, while other mol­ecules in general positions are linked together into ribbons by pairs of C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111004069/fg3210sup1.cif
Contains datablocks CP, CB, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111004069/fg3210CPsup2.hkl
Contains datablock CP

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270111004069/fg3210CBsup3.hkl
Contains datablock CB

CCDC references: 819304; 819305

Comment top

Over the last several years there has been a noticable increase of single-crystal X-ray studies of compounds which are liquid or gaseous under ambient conditions. These studies nowadays include not only straightforward structural determinations of pure compounds, sometimes of new potentially important classes such as room-temperature ionic liquids (Choudhury et al., 2005), but also expand into the emerging area of low-temperature polymorphism (Kirchner et al., 2009) and thus provide fascinating insights into the formation of molecular complexes (cocrystals) in liquid mixtures (Kirchner et al., 2010). Despite such interest, there are still a number of chemical classes left almost untouched. Interesting results were reported recently on polymorphism in such simple compounds as cyclohexanone (Shallard-Brown et al., 2005; Ibberson, 2006; Yufit & Howard, 2008) and cyclohexanol (Ibberson et al., 2008). Surprisingly, the Cambridge Structural Database (Version 5.3.1, November 2010; Allen, 2002) contains no information on the structures of other small cyclic ketones and alcohols. In order to close the gap, we have performed a single-crystal X-ray study of two compounds of this class, namely cyclopentanone (CP) and cyclobutanone (CB), and report here the results obtained.

The crystals of the two compounds turned out to be isostructural (but not isomorphous) and, in both cases, contain two crystallographically independent molecules, one in a general position and one in a special position on a twofold axis, which passes through both atoms of carbonyl group. The geometry of the independent molecules in each compound is identical (Fig. 1). The CP molecules adopt a half-chair conformation, while the CB molecules are planar. The bond lengths and angles in CP and CB are close to calculated values (Mukhopadhyay et al., 2009). Slight elongation of the carbonyl bond in CP [1.2109 (15) and 1.2148 (15) Å] in comparison with CB [1.2016 (16) and 1.2028 (14) Å] corresponds to theoretical calculations and reflects a higher polarity of that bond in CP.

As noted above, the crystals of CP and CB are isostructural; however, the difference in one methylene group between these two molecules slightly distorts the packing. As a result, similarity to the CP orientation and position of the CB molecules in the unit cell can be achieved only by refining the CB structure using a cell with an acute monoclinic angle and an opposite direction of the c axis (Fig 2). In order to maintain consistency of the description of intermolecular interactions in these structures and make the comparisons more simple, the structure of CB has been refined in such a nonstandard setting of the C2/c space group.

The packing of molecules in CP and CB is of note: molecules in general positions form dimers with an antiparallel arrangement of the carbonyl groups and with corresponding O1···C1(-x+1/2, -y+3/2, -z+1) distances of 3.1915 (15) and 3.2295 (13) Å in CP and CB, respectively (Fig. 3). Such an arrangement indicates the presence of strong dipole–dipole interactions between these molecules. The geometrical parameters of these and other intermolecular contacts are given in Table 1. In contrast, the molecules in special positions are linked together in ribbons, parallel to the c direction, by pairs of C—H···O interactions. There are short O···C(carbonyl) contacts [3.2425 (12) and 3.0924 (11)Å in CP and CB, respectively] between molecules in ribbons and in dimers, but in these contacts the carbonyl groups are nonparallel and form O1—C1—O2—C11 torsion angles of -46.90 (8) and -47.91 (8)° in CP and CB, respectively, and therefore can not be regarded as dipole–dipole interactions. The planes of the carbonyl groups are at 57.29 (7) (in CP) and 62.58 (8)° (in CB) to each other, so one of the lone pairs of electrons of the O atom is directed towards the carbonyl C atom of one of dimers.

Thus, these small cyclic ketones show several different types of intermolecular interactions within the same structure. The observed packing pattern is quite different from those found in several polymorphs of cyclohexanone, where the molecules are linked by various C—H···O interactions but not by dipole–dipole interactions (Shallard-Brown et al., 2005; Ibberson, 2006; Yufit & Howard, 2008). Interestingly, solvent cyclopentanone molecules in other crystals either do not interact with each other (Toda et al., 2000) or form C—H···O-linked dimers or chains (Bock et al., 1998; Liu et al., 2006), similar to those found in CP, but no dipole–dipole-linked dimers were observed. To the best of our knowledge, no cocrystals containing cyclobutanone molecules have been reported so far.

Related literature top

For related literature, see: Bock et al. (1998); Choudhury et al. (2005); Ibberson (2006); Ibberson et al. (2008); Kirchner et al. (2009, 2010); Liu et al. (2006); Mukhopadhyay et al. (2009); Shallard-Brown, Watkin & Cowley (2005); Toda et al. (2000); Yufit & Howard (2005, 2008).

Experimental top

The liquids samples were sealed in 0.3 mm borosilicate glass capillaries which were mounted on a diffractometer using a special attachment (Yufit & Howard, 2005). The crystals of both compounds were grown in situ on a diffractometer by flash-freezing of the overcooled liquid at 220 K, followed by partial melting of the resulting polycrystalline material and slow growing of the crystals at 200.5 K. The cylindric crystals formed were then cooled down to 200 K and data were collected at this temperature.

Refinement top

As it was mentioned in the Comment, in order to maintain consistency in the description of the structures of CP and CB, the CB structure has been refined in a nonstandard setting of the C2/c space group with an acute β angle. The data have been collected in a standard setting and then the cell parameters in the input file were changed manually. Also the signs of the L indexes in the hkl file have been changed to the opposite ones with the help of a locally written service program.

Computing details top

For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure and labelling scheme for (a) CP and (b) CB. Displacement ellpsoids are shown at the 50% probability level.
[Figure 2] Fig. 2. The packing of molecules in the structures of (a) CP and (b) CB. The view is along the b axis and H atoms have been omitted for clarity.
[Figure 3] Fig. 3. Fragments of structures of (a) CP and (b) CB, showing the intermolecular contacts. [Symmetry codes: (A) -x+1/2, -y+3/2, -z+1; (B) -x, -y+1, -z+1; (C) x, -y+1, z-1/2.]
(CP) cyclopentan-1-one top
Crystal data top
C5H8OF(000) = 552
Mr = 84.11Dx = 1.152 Mg m3
Monoclinic, C2/cMelting point: 218 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 16.7421 (16) ÅCell parameters from 1202 reflections
b = 9.7941 (8) Åθ = 29.6–2.4°
c = 8.8898 (7) ŵ = 0.08 mm1
β = 93.69 (2)°T = 200 K
V = 1454.7 (2) Å3Cylinder, colourless
Z = 120.5 × 0.3 × 0.3 mm
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
1336 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.035
Graphite monochromatorθmax = 29.5°, θmin = 2.4°
Detector resolution: 8.0 pixels mm-1h = 1523
ω scansk = 1313
6027 measured reflectionsl = 97
1660 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035All H-atom parameters refined
wR(F2) = 0.099 w = 1/[σ2(Fo2) + (0.050P)2 + 0.3P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
1660 reflectionsΔρmax = 0.17 e Å3
132 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0115 (18)
Crystal data top
C5H8OV = 1454.7 (2) Å3
Mr = 84.11Z = 12
Monoclinic, C2/cMo Kα radiation
a = 16.7421 (16) ŵ = 0.08 mm1
b = 9.7941 (8) ÅT = 200 K
c = 8.8898 (7) Å0.5 × 0.3 × 0.3 mm
β = 93.69 (2)°
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
1336 reflections with I > 2σ(I)
6027 measured reflectionsRint = 0.035
1660 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.099All H-atom parameters refined
S = 1.03Δρmax = 0.17 e Å3
1660 reflectionsΔρmin = 0.14 e Å3
132 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.17244 (6)0.63157 (9)0.50785 (12)0.0642 (3)
O20.00000.58323 (9)0.25000.0450 (3)
C10.16762 (6)0.70397 (11)0.39723 (15)0.0442 (3)
C20.20281 (7)0.67435 (12)0.24876 (16)0.0485 (3)
C30.19157 (7)0.80501 (11)0.15710 (17)0.0476 (3)
C40.11695 (7)0.86947 (11)0.21755 (14)0.0436 (3)
C50.12532 (7)0.84020 (12)0.38500 (14)0.0450 (3)
C110.00000.45920 (13)0.25000.0346 (3)
C120.04221 (7)0.36976 (10)0.36852 (14)0.0423 (3)
C130.03880 (7)0.22685 (10)0.29943 (14)0.0442 (3)
H210.1714 (8)0.5987 (15)0.2000 (18)0.071 (4)*
H220.2574 (9)0.6471 (14)0.2676 (17)0.063 (4)*
H310.2383 (8)0.8620 (13)0.1776 (16)0.054 (3)*
H320.1873 (8)0.7885 (14)0.0485 (19)0.065 (4)*
H410.0689 (8)0.8226 (13)0.1728 (16)0.051 (3)*
H420.1128 (7)0.9662 (14)0.1943 (15)0.053 (3)*
H510.1617 (8)0.9040 (14)0.4380 (17)0.064 (4)*
H520.0766 (9)0.8365 (15)0.4355 (18)0.073 (5)*
H1210.0958 (8)0.4046 (14)0.3968 (16)0.061 (4)*
H1220.0096 (8)0.3744 (13)0.4567 (17)0.058 (4)*
H1310.0836 (8)0.2158 (13)0.2380 (15)0.052 (3)*
H1320.0412 (8)0.1537 (14)0.3772 (16)0.056 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0652 (6)0.0616 (5)0.0631 (8)0.0133 (4)0.0172 (5)0.0193 (4)
O20.0551 (6)0.0298 (5)0.0497 (8)0.0000.0006 (5)0.000
C10.0373 (5)0.0424 (5)0.0515 (9)0.0076 (4)0.0084 (5)0.0014 (5)
C20.0397 (5)0.0410 (5)0.0645 (9)0.0051 (4)0.0008 (5)0.0087 (5)
C30.0451 (6)0.0473 (6)0.0518 (9)0.0026 (4)0.0138 (5)0.0053 (5)
C40.0470 (6)0.0397 (5)0.0446 (8)0.0055 (4)0.0068 (5)0.0013 (4)
C50.0445 (5)0.0489 (6)0.0420 (8)0.0027 (4)0.0055 (5)0.0058 (5)
C110.0380 (6)0.0311 (6)0.0353 (9)0.0000.0067 (6)0.000
C120.0526 (6)0.0339 (5)0.0395 (8)0.0016 (4)0.0039 (5)0.0002 (4)
C130.0597 (7)0.0325 (5)0.0406 (8)0.0077 (4)0.0049 (5)0.0018 (4)
Geometric parameters (Å, º) top
O1—C11.2109 (15)C4—H420.972 (13)
O2—C111.2148 (15)C5—H510.972 (15)
C1—C21.5078 (18)C5—H520.957 (15)
C1—C51.5111 (15)C11—C12i1.5103 (14)
C2—C31.5223 (18)C11—C121.5103 (14)
C2—H210.991 (15)C12—C131.5282 (14)
C2—H220.957 (15)C12—H1210.978 (14)
C3—C41.5279 (14)C12—H1220.985 (15)
C3—H310.968 (14)C13—C13i1.521 (2)
C3—H320.977 (16)C13—H1310.961 (13)
C4—C51.5136 (18)C13—H1320.995 (14)
C4—H410.987 (13)
O1—C1—C2126.07 (11)C1—C5—C4104.55 (9)
O1—C1—C5125.59 (12)C1—C5—H51104.8 (8)
C2—C1—C5108.34 (10)C4—C5—H51111.7 (9)
C1—C2—C3105.37 (9)C1—C5—H52110.1 (9)
C1—C2—H21107.5 (9)C4—C5—H52116.1 (9)
C3—C2—H21110.5 (9)H51—C5—H52108.9 (12)
C1—C2—H22108.8 (9)O2—C11—C12i125.45 (6)
C3—C2—H22114.3 (8)O2—C11—C12125.45 (6)
H21—C2—H22110.0 (11)C12i—C11—C12109.10 (11)
C2—C3—C4103.58 (9)C11—C12—C13104.31 (10)
C2—C3—H31108.3 (8)C11—C12—H121111.0 (8)
C4—C3—H31111.4 (8)C13—C12—H121115.6 (8)
C2—C3—H32112.8 (8)C11—C12—H122105.7 (8)
C4—C3—H32114.0 (8)C13—C12—H122110.7 (8)
H31—C3—H32106.8 (12)H121—C12—H122109.1 (12)
C5—C4—C3103.98 (10)C13i—C13—C12103.92 (7)
C5—C4—H41109.2 (8)C13i—C13—H131109.9 (8)
C3—C4—H41109.2 (7)C12—C13—H131108.7 (8)
C5—C4—H42113.3 (8)C13i—C13—H132113.4 (8)
C3—C4—H42112.2 (7)C12—C13—H132112.5 (8)
H41—C4—H42108.8 (11)H131—C13—H132108.3 (10)
O1—C1—C2—C3171.34 (11)C2—C1—C5—C415.14 (12)
C5—C1—C2—C38.45 (12)C3—C4—C5—C132.72 (11)
C1—C2—C3—C428.46 (13)O2—C11—C12—C13168.18 (5)
C2—C3—C4—C538.05 (12)C12i—C11—C12—C1311.82 (5)
O1—C1—C5—C4165.06 (11)C11—C12—C13—C13i30.96 (13)
Symmetry code: (i) x, y, z+1/2.
(CB) cyclobutan-1-one top
Crystal data top
C4H6ODx = 1.151 Mg m3
Mr = 70.09Melting point: 218 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 15.5022 (16) ÅCell parameters from 1067 reflections
b = 9.0662 (9) Åθ = 2.6–30.5°
c = 8.6531 (7) ŵ = 0.08 mm1
β = 85.83 (3)°T = 200 K
V = 1212.9 (2) Å3Cylinder, colourless
Z = 120.5 × 0.35 × 0.35 mm
F(000) = 456
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
1127 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 30.5°, θmin = 2.6°
Detector resolution: 5.6 pixels mm-1h = 1622
ω scansk = 1212
5379 measured reflectionsl = 77
1440 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: difference Fourier map
wR(F2) = 0.121All H-atom parameters refined
S = 1.06 w = 1/[σ2(Fo2) + (0.070P)2 + 0.150P],
where P = (Fo2 + 2Fc2)/3
1440 reflections(Δ/σ)max < 0.001
106 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C4H6OV = 1212.9 (2) Å3
Mr = 70.09Z = 12
Monoclinic, C2/cMo Kα radiation
a = 15.5022 (16) ŵ = 0.08 mm1
b = 9.0662 (9) ÅT = 200 K
c = 8.6531 (7) Å0.5 × 0.35 × 0.35 mm
β = 85.83 (3)°
Data collection top
Bruker SMART CCD 6000 area-detector
diffractometer
1127 reflections with I > 2σ(I)
5379 measured reflectionsRint = 0.036
1440 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.121All H-atom parameters refined
S = 1.06Δρmax = 0.23 e Å3
1440 reflectionsΔρmin = 0.15 e Å3
106 parameters
Special details top

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.16529 (5)0.62858 (10)0.49939 (11)0.0558 (3)
O20.00000.59104 (11)0.25000.0470 (3)
C10.16682 (6)0.70470 (11)0.38539 (13)0.0408 (3)
C20.20760 (8)0.68827 (13)0.22340 (16)0.0489 (3)
C30.16675 (9)0.83723 (13)0.18330 (17)0.0536 (4)
C40.12918 (8)0.85412 (11)0.35121 (16)0.0479 (3)
C110.00000.45850 (15)0.25000.0351 (3)
C120.04292 (8)0.34379 (12)0.34572 (17)0.0456 (3)
C130.00000.22420 (18)0.25000.0561 (5)
H130.0421 (9)0.1647 (17)0.190 (2)0.071 (4)*
H210.1859 (9)0.6060 (16)0.1639 (18)0.064 (4)*
H220.2693 (10)0.6906 (17)0.2224 (19)0.069 (4)*
H310.1201 (10)0.8302 (17)0.113 (2)0.072 (5)*
H320.2084 (9)0.9098 (18)0.1445 (19)0.069 (4)*
H410.0674 (9)0.8597 (15)0.3670 (17)0.059 (4)*
H420.1562 (10)0.9319 (19)0.413 (2)0.074 (5)*
H1210.0225 (9)0.3462 (15)0.4496 (19)0.057 (4)*
H1220.1040 (9)0.3508 (16)0.3344 (17)0.063 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0602 (5)0.0582 (5)0.0500 (7)0.0060 (4)0.0111 (4)0.0156 (4)
O20.0567 (6)0.0391 (5)0.0466 (9)0.0000.0129 (5)0.000
C10.0386 (5)0.0400 (5)0.0445 (8)0.0075 (3)0.0075 (4)0.0020 (4)
C20.0486 (6)0.0453 (6)0.0518 (10)0.0079 (4)0.0038 (5)0.0043 (5)
C30.0719 (8)0.0447 (6)0.0449 (10)0.0134 (5)0.0094 (6)0.0055 (5)
C40.0588 (7)0.0373 (5)0.0477 (10)0.0017 (4)0.0055 (5)0.0011 (4)
C110.0350 (6)0.0416 (6)0.0284 (10)0.0000.0011 (5)0.000
C120.0490 (6)0.0473 (6)0.0404 (10)0.0081 (4)0.0030 (5)0.0047 (4)
C130.0820 (12)0.0387 (8)0.0462 (13)0.0000.0063 (9)0.000
Geometric parameters (Å, º) top
O1—C11.2028 (14)C4—H410.959 (13)
O2—C111.2016 (16)C4—H420.998 (17)
C1—C21.5026 (18)C11—C121.5135 (14)
C1—C41.5126 (15)C11—C12i1.5135 (14)
C2—C31.5419 (18)C12—C131.5442 (17)
C2—H210.980 (14)C12—H1210.931 (16)
C2—H220.956 (16)C12—H1220.947 (14)
C3—C41.533 (2)C13—C12i1.5443 (17)
C3—H310.981 (16)C13—H130.967 (15)
C3—H320.965 (16)
O1—C1—C2133.63 (11)C3—C4—H41116.6 (9)
O1—C1—C4133.58 (11)C1—C4—H42110.1 (9)
C2—C1—C492.78 (9)C3—C4—H42115.9 (9)
C1—C2—C388.35 (9)H41—C4—H42109.9 (12)
C1—C2—H21115.4 (9)O2—C11—C12133.41 (6)
C3—C2—H21112.7 (8)O2—C11—C12i133.40 (6)
C1—C2—H22111.0 (10)C12—C11—C12i93.19 (12)
C3—C2—H22113.9 (10)C11—C12—C1388.00 (9)
H21—C2—H22113.2 (12)C11—C12—H121112.3 (9)
C4—C3—C290.46 (9)C13—C12—H121113.9 (9)
C4—C3—H31110.4 (10)C11—C12—H122111.9 (9)
C2—C3—H31114.6 (9)C13—C12—H122117.3 (9)
C4—C3—H32117.4 (10)H121—C12—H122111.4 (12)
C2—C3—H32113.5 (9)C12—C13—C12i90.80 (12)
H31—C3—H32109.6 (14)C12—C13—H13112.2 (9)
C1—C4—C388.31 (9)C12i—C13—H13113.9 (10)
C1—C4—H41114.5 (8)
O1—C1—C2—C3178.28 (12)C2—C3—C4—C12.25 (8)
C4—C1—C2—C32.30 (9)O2—C11—C12—C13180.0
C1—C2—C3—C42.26 (8)C12i—C11—C12—C130.0
O1—C1—C4—C3178.27 (12)C11—C12—C13—C12i0.0
C2—C1—C4—C32.31 (9)
Symmetry code: (i) x, y, z+1/2.

Experimental details

(CP)(CB)
Crystal data
Chemical formulaC5H8OC4H6O
Mr84.1170.09
Crystal system, space groupMonoclinic, C2/cMonoclinic, C2/c
Temperature (K)200200
a, b, c (Å)16.7421 (16), 9.7941 (8), 8.8898 (7)15.5022 (16), 9.0662 (9), 8.6531 (7)
β (°) 93.69 (2) 85.83 (3)
V3)1454.7 (2)1212.9 (2)
Z1212
Radiation typeMo KαMo Kα
µ (mm1)0.080.08
Crystal size (mm)0.5 × 0.3 × 0.30.5 × 0.35 × 0.35
Data collection
DiffractometerBruker SMART CCD 6000 area-detector
diffractometer
Bruker SMART CCD 6000 area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
6027, 1660, 1336 5379, 1440, 1127
Rint0.0350.036
(sin θ/λ)max1)0.6920.713
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.099, 1.03 0.039, 0.121, 1.06
No. of reflections16601440
No. of parameters132106
H-atom treatmentAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.17, 0.140.23, 0.15

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Table 1. Parameters of intermolecular contacts in CP and CB (Å, °) top
CompoundD—H···AD—HH···AD···AD—H···A
CPC12—H122···O2i0.985 (15)2.655 (15)3.5384 (13)149.4 (11)
CBC12—H121···O2i0.931 (16)2.659 (16)3.5625 (13)163.7 (12)
CPO2···C13.1915 (15)
CBO2···C13.2295 (13)
CPO1···C1ii3.2425 (12)
CBO1···C1ii3.0924 (11)
Symmetry codes: (i) -x+1/2, -y+3/2, -z+1; (ii) -x, -y+1, -z+1 and x, -y+1, z-1/2. [Author: code (ii) does not match that given in the Comment and Fig. 3 of (-x+1/2, -y+3/2, -z+1), i.e. code (i)]
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds