A new polymorph of dimesitylborinic acid

Kuhlmann, M.; Baumgartner, T.; Parvez, M.

doi:10.1107/S1600536808015638

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1185

doi:10.1107/S1600536808015638

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A new polymorph of dimesitylborinic acid

Matthias Kuhlmann,^a Thomas Baumgartner ^a and Masood Parvez ^a ^*

^aDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: parvez@ucalgary.ca

(Received 16 May 2008; accepted 23 May 2008; online 7 June 2008)

A new polymorph of dimesitylborinic acid (or hydroxydimesitylborane), C₁₈H₂₃BO, showcasing different crystal packing and symmetry, complements the previously reported polymorph [Weese, Bartlett, Murray, Olmstead & Power (1987 ). Inorg. Chem. 26, 2409–2413; Entwistle, Batsanov & Marder (2007 ). Acta Cryst. E63, o2639–o2641]. The structure of the title compound contains only one molecule in the asymmetric unit, and no O—H⋯O interactions are observed. However, molecules are linked by weak intermolecuar O—H⋯π(arene) interactions to form centrosymmetric dimers.

Related literature

For related literature, see: Cornet et al. (2003 ); Entwistle et al. (2007); Fraenk et al. (2001 ); Kuhlmann et al. (2008 ); Weese et al. (1987).

Experimental

Crystal data

C₁₈H₂₃BO
M_r = 266.17
Monoclinic, P 2₁ /c
a = 8.942 (4) Å
b = 8.801 (2) Å
c = 19.947 (8) Å
β = 97.800 (16)°
V = 1555.3 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 173 (2) K
0.32 × 0.24 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.979, T_max = 0.992
6119 measured reflections
3542 independent reflections
2728 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.134
S = 0.91
3542 reflections
188 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cgⁱ	0.84 (2)	2.83 (2)	3.523 (2)	141 (2)
Symmetry code: (i) -x, -y, -z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015638/om2237sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808015638/om2237Isup2.hkl

checkCIF report

Comment top

In the course of our studies on the synthesis and photophysical properties of boron-functionalized dithieno[3,2-b;2',3'-d]phospholes (Kuhlmann et al., 2008), we obtained a new polymorph of the title compound. It crystallizes in space group P2₁/c, which is distinct from the previously reported space group C2/c (Weese et al., 1987; Entwistle et al., 2007).

The structure is composed of unique molecules (Fig. 1) separated by normal van der Waals distances. The mean planes of the phenyl rings are inclined at approximately right angles (86.09 (4)°) with respect to each other. The structure is devoid of any classical hydrogen bonding despite the presence of a hydroxyl group. The previously reported polymorph crystallized as tetramers due to hydrogen bonding involving the OH groups (Weese et al., 1987). There are no indications of π-π stacking interactions between the phenyl groups of the symmetry related molecules in the title compound. However, the hydroxyl group is oriented towards a phenyl ring (C11-C16), thus linking the molecules by rather weak intermolecular O—H···π(arene) interactions to form centrosymmetric dimers about inversion centers (Fig. 2). The boron centers are planar with C2—B1—C11 angle 123.21 (12)°, compared to a wider corresponding angle of 126.0 (4)° reported in the other polymorph (Weese et al., 1987). The structures of trifluoromethyl analogues have also been reported, and they exhibit a similar molecular conformation (Fraenk et al., 2001; Cornet et al., 2003).

Related literature top

For related literature, see: Cornet et al. (2003); Entwistle et al. (2007); Fraenk et al. (2001); Kuhlmann et al. (2008); Sheldrick (2008); Weese et al. (1987). Cg is the centroid of the C11–C16 phenyl ring.

Experimental top

The title compound was obtained as hydrolysis by-product in the synthesis of 2-(dimetsitylboryl)-5-phenyl-dithieno[3,2 - b;2',3'-d]phosphole, during the recrystallization of the sample from a concentrated pentane solution at 277 K.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the title compound with displacement ellipsoids plotted at the 50% probability level. Only three H atoms on C9 and C18 are shown.
	Fig. 2. Unit cell packing as viewed down the b direction showing intermolecular O—H···π(arene) interactions with dashed lines.

hydroxydimesitylborane top

Crystal data top

C₁₈H₂₃BO	F(000) = 576
M_r = 266.17	D_x = 1.137 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6119 reflections
a = 8.942 (4) Å	θ = 3.3–27.5°
b = 8.801 (2) Å	µ = 0.07 mm⁻¹
c = 19.947 (8) Å	T = 173 K
β = 97.800 (16)°	Block, yellow
V = 1555.3 (10) Å³	0.32 × 0.24 × 0.12 mm
Z = 4

Data collection top

Nonius KappaCCD diffractometer	3542 independent reflections
Radiation source: fine-focus sealed tube	2728 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω and ϕ scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −11→11
T_min = 0.979, T_max = 0.992	k = −11→11
6119 measured reflections	l = −25→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ²(F_o²) + (0.072P)² + 0.71P] where P = (F_o² + 2F_c²)/3
3542 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₈H₂₃BO	V = 1555.3 (10) Å³
M_r = 266.17	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.942 (4) Å	µ = 0.07 mm⁻¹
b = 8.801 (2) Å	T = 173 K
c = 19.947 (8) Å	0.32 × 0.24 × 0.12 mm
β = 97.800 (16)°

Data collection top

Nonius KappaCCD diffractometer	3542 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	2728 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.992	R_int = 0.023
6119 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.26 e Å⁻³
3542 reflections	Δρ_min = −0.19 e Å⁻³
188 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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.11790 (13)	−0.31566 (13)	−0.00945 (5)	0.0401 (3)
H1	0.076 (2)	−0.251 (2)	−0.0366 (10)	0.048*
B1	0.08930 (17)	−0.28800 (17)	0.05445 (8)	0.0269 (3)
C2	0.17055 (15)	−0.39649 (14)	0.11108 (6)	0.0255 (3)
C3	0.32785 (15)	−0.42311 (15)	0.11607 (7)	0.0278 (3)
C4	0.39909 (15)	−0.51699 (15)	0.16679 (7)	0.0309 (3)
H4	0.5049	−0.5324	0.1698	0.037*
C5	0.32018 (16)	−0.58890 (15)	0.21314 (7)	0.0316 (3)
C6	0.16562 (16)	−0.56426 (15)	0.20763 (7)	0.0310 (3)
H6	0.1095	−0.6138	0.2384	0.037*
C7	0.09009 (15)	−0.46888 (15)	0.15823 (7)	0.0276 (3)
C8	0.42383 (17)	−0.35135 (18)	0.06779 (8)	0.0374 (4)
H8A	0.5308	−0.3633	0.0857	0.045*
H8B	0.3995	−0.2430	0.0628	0.045*
H8C	0.4034	−0.4013	0.0236	0.045*
C9	0.3997 (2)	−0.68880 (19)	0.26809 (8)	0.0446 (4)
H9A	0.5077	−0.6926	0.2641	0.067*	0.50
H9B	0.3574	−0.7916	0.2636	0.067*	0.50
H9C	0.3858	−0.6472	0.3124	0.067*	0.50
H9D	0.3262	−0.7283	0.2960	0.067*	0.50
H9E	0.4765	−0.6294	0.2965	0.067*	0.50
H9F	0.4481	−0.7737	0.2476	0.067*	0.50
C10	−0.07788 (16)	−0.44837 (18)	0.15670 (8)	0.0364 (3)
H10A	−0.1137	−0.5144	0.1907	0.044*
H10B	−0.1295	−0.4752	0.1117	0.044*
H10C	−0.0995	−0.3422	0.1666	0.044*
C11	−0.02005 (15)	−0.15448 (14)	0.06966 (7)	0.0265 (3)
C12	−0.17091 (15)	−0.15062 (15)	0.03816 (7)	0.0286 (3)
C13	−0.27017 (16)	−0.04211 (16)	0.05784 (7)	0.0320 (3)
H13	−0.3721	−0.0420	0.0369	0.038*
C14	−0.22404 (17)	0.06574 (16)	0.10723 (7)	0.0337 (3)
C15	−0.07360 (17)	0.06623 (15)	0.13554 (7)	0.0330 (3)
H15	−0.0392	0.1424	0.1677	0.040*
C16	0.02899 (16)	−0.04183 (15)	0.11824 (7)	0.0292 (3)
C17	−0.23031 (17)	−0.26522 (18)	−0.01535 (8)	0.0367 (3)
H17A	−0.3408	−0.2611	−0.0228	0.044*
H17B	−0.1976	−0.3674	−0.0002	0.044*
H17C	−0.1910	−0.2415	−0.0577	0.044*
C18	−0.3345 (2)	0.17870 (19)	0.12935 (10)	0.0471 (4)
H18A	−0.4347	0.1610	0.1040	0.071*	0.50
H18B	−0.3013	0.2821	0.1206	0.071*	0.50
H18C	−0.3392	0.1664	0.1778	0.071*	0.50
H18D	−0.2821	0.2453	0.1643	0.071*	0.50
H18E	−0.4155	0.1242	0.1477	0.071*	0.50
H18F	−0.3776	0.2399	0.0904	0.071*	0.50
C19	0.18953 (18)	−0.03689 (18)	0.15248 (8)	0.0405 (4)
H19A	0.2080	0.0600	0.1763	0.049*
H19B	0.2584	−0.0468	0.1185	0.049*
H19C	0.2068	−0.1207	0.1850	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0500 (7)	0.0443 (6)	0.0276 (5)	0.0133 (5)	0.0115 (5)	0.0046 (4)
B1	0.0270 (7)	0.0273 (7)	0.0274 (8)	−0.0023 (6)	0.0068 (6)	−0.0004 (6)
C2	0.0284 (7)	0.0225 (6)	0.0259 (6)	0.0005 (5)	0.0056 (5)	−0.0035 (5)
C3	0.0298 (7)	0.0247 (6)	0.0298 (7)	−0.0015 (5)	0.0066 (5)	−0.0061 (5)
C4	0.0276 (7)	0.0282 (7)	0.0359 (8)	0.0022 (5)	0.0012 (6)	−0.0078 (5)
C5	0.0378 (8)	0.0267 (7)	0.0286 (7)	0.0017 (6)	−0.0012 (6)	−0.0035 (5)
C6	0.0381 (8)	0.0282 (7)	0.0270 (7)	−0.0007 (6)	0.0059 (6)	0.0002 (5)
C7	0.0309 (7)	0.0264 (6)	0.0260 (6)	0.0010 (5)	0.0060 (5)	−0.0030 (5)
C8	0.0321 (7)	0.0411 (8)	0.0409 (8)	−0.0018 (6)	0.0119 (6)	−0.0009 (6)
C9	0.0470 (9)	0.0417 (9)	0.0418 (9)	0.0063 (7)	−0.0054 (7)	0.0067 (7)
C10	0.0331 (8)	0.0413 (8)	0.0368 (8)	0.0021 (6)	0.0124 (6)	0.0079 (6)
C11	0.0302 (7)	0.0247 (6)	0.0251 (6)	0.0009 (5)	0.0055 (5)	0.0032 (5)
C12	0.0308 (7)	0.0260 (6)	0.0290 (7)	−0.0008 (5)	0.0042 (5)	0.0032 (5)
C13	0.0289 (7)	0.0315 (7)	0.0358 (8)	0.0019 (5)	0.0048 (6)	0.0051 (6)
C14	0.0380 (8)	0.0271 (7)	0.0380 (8)	0.0059 (6)	0.0122 (6)	0.0043 (6)
C15	0.0431 (8)	0.0249 (7)	0.0313 (7)	0.0009 (6)	0.0057 (6)	−0.0032 (5)
C16	0.0341 (7)	0.0255 (6)	0.0278 (7)	0.0004 (5)	0.0032 (6)	0.0029 (5)
C17	0.0350 (8)	0.0383 (8)	0.0360 (8)	−0.0045 (6)	0.0012 (6)	−0.0047 (6)
C18	0.0457 (9)	0.0391 (9)	0.0590 (11)	0.0129 (7)	0.0168 (8)	−0.0020 (7)
C19	0.0391 (8)	0.0373 (8)	0.0424 (8)	0.0021 (6)	−0.0044 (7)	−0.0085 (7)

Geometric parameters (Å, º) top

O1—B1	1.3556 (19)	C10—H10B	0.9800
O1—H1	0.84 (2)	C10—H10C	0.9800
B1—C2	1.579 (2)	C11—C12	1.409 (2)
B1—C11	1.584 (2)	C11—C16	1.4139 (19)
C2—C7	1.4113 (19)	C12—C13	1.3958 (19)
C2—C3	1.4161 (19)	C12—C17	1.512 (2)
C3—C4	1.3918 (19)	C13—C14	1.390 (2)
C3—C8	1.512 (2)	C13—H13	0.9500
C4—C5	1.389 (2)	C14—C15	1.386 (2)
C4—H4	0.9500	C14—C18	1.509 (2)
C5—C6	1.388 (2)	C15—C16	1.397 (2)
C5—C9	1.506 (2)	C15—H15	0.9500
C6—C7	1.3968 (19)	C16—C19	1.504 (2)
C6—H6	0.9500	C17—H17A	0.9800
C7—C10	1.509 (2)	C17—H17B	0.9800
C8—H8A	0.9800	C17—H17C	0.9800
C8—H8B	0.9800	C18—H18A	0.9800
C8—H8C	0.9800	C18—H18B	0.9800
C9—H9A	0.9800	C18—H18C	0.9800
C9—H9B	0.9800	C18—H18D	0.9800
C9—H9C	0.9800	C18—H18E	0.9800
C9—H9D	0.9800	C18—H18F	0.9800
C9—H9E	0.9800	C19—H19A	0.9800
C9—H9F	0.9800	C19—H19B	0.9800
C10—H10A	0.9800	C19—H19C	0.9800

B1—O1—H1	111.0 (13)	H10A—C10—H10C	109.5
O1—B1—C2	115.90 (12)	H10B—C10—H10C	109.5
O1—B1—C11	120.89 (12)	C12—C11—C16	118.54 (12)
C2—B1—C11	123.21 (12)	C12—C11—B1	120.73 (12)
C7—C2—C3	118.02 (12)	C16—C11—B1	120.62 (12)
C7—C2—B1	121.54 (12)	C13—C12—C11	119.86 (13)
C3—C2—B1	120.43 (12)	C13—C12—C17	118.63 (13)
C4—C3—C2	120.10 (12)	C11—C12—C17	121.47 (12)
C4—C3—C8	117.87 (13)	C14—C13—C12	121.86 (13)
C2—C3—C8	122.03 (13)	C14—C13—H13	119.1
C5—C4—C3	122.04 (13)	C12—C13—H13	119.1
C5—C4—H4	119.0	C15—C14—C13	117.97 (13)
C3—C4—H4	119.0	C15—C14—C18	121.08 (14)
C6—C5—C4	117.78 (13)	C13—C14—C18	120.95 (14)
C6—C5—C9	121.02 (13)	C14—C15—C16	122.05 (13)
C4—C5—C9	121.20 (14)	C14—C15—H15	119.0
C5—C6—C7	122.04 (13)	C16—C15—H15	119.0
C5—C6—H6	119.0	C15—C16—C11	119.59 (13)
C7—C6—H6	119.0	C15—C16—C19	119.10 (13)
C6—C7—C2	120.00 (13)	C11—C16—C19	121.30 (12)
C6—C7—C10	118.09 (12)	C12—C17—H17A	109.5
C2—C7—C10	121.91 (12)	C12—C17—H17B	109.5
C3—C8—H8A	109.5	H17A—C17—H17B	109.5
C3—C8—H8B	109.5	C12—C17—H17C	109.5
H8A—C8—H8B	109.5	H17A—C17—H17C	109.5
C3—C8—H8C	109.5	H17B—C17—H17C	109.5
H8A—C8—H8C	109.5	C14—C18—H18A	109.5
H8B—C8—H8C	109.5	C14—C18—H18B	109.5
C5—C9—H9A	109.5	H18A—C18—H18B	109.5
C5—C9—H9B	109.5	C14—C18—H18C	109.5
H9A—C9—H9B	109.5	H18A—C18—H18C	109.5
C5—C9—H9C	109.5	H18B—C18—H18C	109.5
H9A—C9—H9C	109.5	C14—C18—H18D	109.5
H9B—C9—H9C	109.5	H18A—C18—H18D	141.1
C5—C9—H9D	109.5	H18B—C18—H18D	56.3
H9A—C9—H9D	141.1	H18C—C18—H18D	56.3
H9B—C9—H9D	56.3	C14—C18—H18E	109.5
H9C—C9—H9D	56.3	H18A—C18—H18E	56.3
C5—C9—H9E	109.5	H18B—C18—H18E	141.1
H9A—C9—H9E	56.3	H18C—C18—H18E	56.3
H9B—C9—H9E	141.1	H18D—C18—H18E	109.5
H9C—C9—H9E	56.3	C14—C18—H18F	109.5
H9D—C9—H9E	109.5	H18A—C18—H18F	56.3
C5—C9—H9F	109.5	H18B—C18—H18F	56.3
H9A—C9—H9F	56.3	H18C—C18—H18F	141.1
H9B—C9—H9F	56.3	H18D—C18—H18F	109.5
H9C—C9—H9F	141.1	H18E—C18—H18F	109.5
H9D—C9—H9F	109.5	C16—C19—H19A	109.5
H9E—C9—H9F	109.5	C16—C19—H19B	109.5
C7—C10—H10A	109.5	H19A—C19—H19B	109.5
C7—C10—H10B	109.5	C16—C19—H19C	109.5
H10A—C10—H10B	109.5	H19A—C19—H19C	109.5
C7—C10—H10C	109.5	H19B—C19—H19C	109.5

O1—B1—C2—C7	−130.25 (14)	O1—B1—C11—C12	58.47 (18)
C11—B1—C2—C7	49.51 (18)	C2—B1—C11—C12	−121.28 (14)
O1—B1—C2—C3	50.12 (18)	O1—B1—C11—C16	−125.45 (15)
C11—B1—C2—C3	−130.12 (14)	C2—B1—C11—C16	54.80 (18)
C7—C2—C3—C4	−0.66 (18)	C16—C11—C12—C13	−3.41 (19)
B1—C2—C3—C4	178.98 (12)	B1—C11—C12—C13	172.75 (12)
C7—C2—C3—C8	179.76 (12)	C16—C11—C12—C17	178.63 (13)
B1—C2—C3—C8	−0.60 (19)	B1—C11—C12—C17	−5.21 (19)
C2—C3—C4—C5	0.9 (2)	C11—C12—C13—C14	1.3 (2)
C8—C3—C4—C5	−179.46 (13)	C17—C12—C13—C14	179.29 (13)
C3—C4—C5—C6	−0.1 (2)	C12—C13—C14—C15	2.0 (2)
C3—C4—C5—C9	−179.37 (13)	C12—C13—C14—C18	−177.96 (14)
C4—C5—C6—C7	−1.0 (2)	C13—C14—C15—C16	−3.1 (2)
C9—C5—C6—C7	178.25 (13)	C18—C14—C15—C16	176.82 (14)
C5—C6—C7—C2	1.3 (2)	C14—C15—C16—C11	1.0 (2)
C5—C6—C7—C10	−179.50 (13)	C14—C15—C16—C19	−178.29 (14)
C3—C2—C7—C6	−0.42 (18)	C12—C11—C16—C15	2.32 (19)
B1—C2—C7—C6	179.94 (12)	B1—C11—C16—C15	−173.84 (12)
C3—C2—C7—C10	−179.59 (12)	C12—C11—C16—C19	−178.42 (13)
B1—C2—C7—C10	0.77 (19)	B1—C11—C16—C19	5.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cgⁱ	0.84 (2)	2.83 (2)	3.523 (2)	141 (2)

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃BO
M_r	266.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	8.942 (4), 8.801 (2), 19.947 (8)
β (°)	97.800 (16)
V (Å³)	1555.3 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.32 × 0.24 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.979, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	6119, 3542, 2728
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 0.91
No. of reflections	3542
No. of parameters	188
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.19

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cgⁱ	0.84 (2)	2.83 (2)	3.523 (2)	141 (2)

Symmetry code: (i) −x, −y, −z.

References

Blessing, R. H. (1997). J. Appl. Cryst. 30, 421–426. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Entwistle, C. D., Batsanov, A. S. & Marder, T. B. (2007). Acta Cryst. E63, o2639–o2641. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fraenk, W., Klapotke, T. M., Krumm, B., Mayer, P., Noth, H., Piotrowski, H. & Suter, M. (2001). J. Fluorine Chem. 112, 73–81. Web of Science CSD CrossRef CAS Google Scholar
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Kuhlmann, M., Boone, M. P. & Baumgartner, T. (2008). Unpublished. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Weese, K. J., Bartlett, R. A., Murray, B. D., Olmstead, M. M. & Power, P. P. (1987). Inorg. Chem. 26, 2409–2413. CSD CrossRef CAS Web of Science Google Scholar

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Volume 64| Part 7| July 2008| Page o1185

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