O-4-Chloro­benzoyl diphenyl­seleno­phosphinate

Cholewinski, G.; Chojnacki, J.; Pikies, J.; Rachon, J.

doi:10.1107/S1600536809009313

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o855

doi:10.1107/S1600536809009313

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O-4-Chlorobenzoyl diphenylselenophosphinate

Grzegorz Cholewinski,^a Jaroslaw Chojnacki,^a ^* Jerzy Pikies ^a and Janusz Rachon ^a

^aChemical Faculty, Gdansk University of Technology, Narutowicza 11/12, Gdansk PL-80233, Poland
^*Correspondence e-mail: jaroslaw.chojnacki@chem.pg.gda.pl

(Received 23 January 2009; accepted 13 March 2009; online 25 March 2009)

The title compound, C₁₉H₁₄ClO₂PSe, was obtained in the reaction of the diphenylmonoselenophosphinic acid ammonium salt with 4-chlorobenzoyl chloride. The dihedral angle between the P-bonded aromatic rings is 72.64 (14)°. Packing of the molecules in the crystal is reinforced by π–π stacking interactions between two inversion-related 4-chlorobenzene rings [centroid-centroid separation = 4.189 (2) Å] and a C—H⋯O interaction also occurs.

Related literature

Syntheses of O-acyl monoselenophosphates have already been described by Rachon et al. (2005 ); Mielniczak & Łopusinski (2001 ). For a related O-acyl derivative, see Cholewinski et al. (2009 ). For related O-alkyl or O-aryl derivatives, see: Lepicard et al. (1969 ); Balakrishna et al. (2002 , 2005 ); Mague et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₄ClO₂PSe
M_r = 419.68
Monoclinic, P 2₁ /c
a = 9.3390 (5) Å
b = 9.7132 (5) Å
c = 19.1353 (15) Å
β = 97.059 (6)°
V = 1722.64 (19) Å³
Z = 4
Mo Kα radiation
μ = 2.44 mm⁻¹
T = 120 K
0.46 × 0.33 × 0.26 mm

Data collection

Oxford Diffraction KM-4-CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.325, T_max = 0.53
14128 measured reflections
4158 independent reflections
3376 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.162
S = 1.16
4158 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 1.82 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O2ⁱ	0.95	2.59	3.359 (6)	138
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; 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: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009313/ez2164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009313/ez2164Isup2.hkl

checkCIF report

Comment top

O-acyl monoselenophosphates were studied as part of a search for potential selenoacylating agents. O-4-chlorobenzoyl-diphenylmonoselenophosphinate was obtained in the reaction of diphenylmonoselenophosphinic acid ammonium salt with 4-chlorobenzoyl chloride (Rachon et al. 2005).

The title compound, C₁₉H₁₄ClO₂PSe, together with O-pivaloyl- diphenylselenophosphinate, reported in our preceding paper (Cholewinski et al., 2009) are the first reported X-ray diffraction structures of O-acyl derivatives of diphenylmonoselenophosphinic acid. Several other monoselenophosphinates, such as O-alkyl esters have been characterized by X-ray diffraction (Lepicard et al., 1969; Balakrishna et al., 2005; Balakrishna et al., 2002; Mague et al., 2007).

The P–Se bond length is in the usual range, while the P–O bond is longer than in O-aryl or O-alkyl derivatives, but very close to the value for the other O-acyl derivative, reported in our preceding paper (Cholewinski et al., 2009). Unlike the pivaloyl analogue, no phenyl ring is close to being synplanar with the Se–P–C plane. The smallest Se–P–C–C torsion angle is relatively large at 25.7 (4)°. Noteworthy is that the carboxyl group is twisted in relation to the adjacent phenyl ring, forming a dihedral angle between the C1–C6 phenyl ring and the plane defined by O1/C7/O2 of 11.6 (7)°.

Packing of O-4-chlorobenzoyl-diphenylmonoselenophosphinate molecules in the crystal is reinforced by π - π stacking interactions between two adjacent 4-chlorobenzene rings residing close to a symmetry centre. The centroid to centroid distance is 4.189 (2) Å, the dihedral angle between the planes is α=0.0° and the angle between the vector span on the centroids and the vector normal to the ring is β=35.08°. No classical hydrogen bonds are present, however a weak C–H···O interaction link molecules into chains along the a-axis.

Related literature top

Syntheses of O-acyl monoselenophosphates have already been described by Rachon et al. (2005). For a related O-acyl derivative, see Cholewinski et al. (2009). For related O-alkyl or O-aryl derivatives, see: Lepicard et al. (1969); Balakrishna et al. (2002, 2005); Mague et al. (2007).

For related literature, see: Mielniczak & Łopusinski (2001).

Experimental top

O-4-chlorobenzoyl-diphenylmonoselenophosphinate was obtained in the reaction of diphenylmonoselenophosphinic acid ammonium salt (Mielniczak et al., 2001) with 4-chlorobenzoyl chloride in 46% yield according to Rachon et al. (2005). The compound which was encoded in this paper as 2t, melts at 105-107 °C. Relevant ¹H, ¹³C, ³¹P NMR, MS and IR spectra were recorded and are consistent with the formula anticipated - see the supporting information for the article cited.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); 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: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. View of the title compound showing the atom-numbering scheme (50% probability displacement ellipsoids).

O-4-Chlorobenzoyl diphenylselenophosphinate top

Crystal data top

C₁₉H₁₄ClO₂PSe	F(000) = 840
M_r = 419.68	D_x = 1.618 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 379(2) K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.3390 (5) Å	Cell parameters from 9084 reflections
b = 9.7132 (5) Å	θ = 2.1–32.4°
c = 19.1353 (15) Å	µ = 2.44 mm⁻¹
β = 97.059 (6)°	T = 120 K
V = 1722.64 (19) Å³	Prism, colourless
Z = 4	0.46 × 0.33 × 0.26 mm

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	4158 independent reflections
Radiation source: enhance	3376 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ω scans (0.75° width)	θ_max = 28°, θ_min = 2.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −12→12
T_min = 0.325, T_max = 0.53	k = −12→12
14128 measured reflections	l = −21→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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.162	H-atom parameters constrained
S = 1.16	w = 1/[σ²(F_o²) + (0.0811P)² + 5.5587P] where P = (F_o² + 2F_c²)/3
4158 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 1.82 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₉H₁₄ClO₂PSe	V = 1722.64 (19) Å³
M_r = 419.68	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3390 (5) Å	µ = 2.44 mm⁻¹
b = 9.7132 (5) Å	T = 120 K
c = 19.1353 (15) Å	0.46 × 0.33 × 0.26 mm
β = 97.059 (6)°

Data collection top

Oxford Diffraction KM-4-CCD diffractometer	4158 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	3376 reflections with I > 2σ(I)
T_min = 0.325, T_max = 0.53	R_int = 0.045
14128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.162	H-atom parameters constrained
S = 1.16	Δρ_max = 1.82 e Å⁻³
4158 reflections	Δρ_min = −0.56 e Å⁻³
217 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Se1	0.28670 (5)	1.03290 (5)	0.35818 (2)	0.02233 (16)
Cl3	0.57203 (12)	0.18536 (11)	0.48614 (6)	0.0244 (2)
P1	0.15102 (11)	0.87791 (11)	0.31430 (5)	0.0146 (2)
O1	0.2030 (3)	0.7199 (3)	0.33713 (15)	0.0179 (6)
O2	0.3944 (3)	0.7246 (4)	0.27566 (17)	0.0242 (7)
C1	0.3808 (4)	0.5449 (4)	0.3593 (2)	0.0167 (8)
C2	0.3182 (5)	0.5004 (5)	0.4180 (2)	0.0206 (9)
H2	0.2362	0.5467	0.4314	0.025*
C3	0.3764 (5)	0.3881 (5)	0.4567 (2)	0.0232 (9)
H3	0.3361	0.3584	0.4974	0.028*
C4	0.4933 (5)	0.3202 (4)	0.4353 (2)	0.0186 (8)
C5	0.5533 (5)	0.3590 (5)	0.3756 (2)	0.0197 (8)
H5	0.631	0.3083	0.3606	0.024*
C6	0.4977 (5)	0.4734 (5)	0.3380 (2)	0.0196 (8)
H6	0.5394	0.5031	0.2977	0.023*
C7	0.3321 (4)	0.6701 (5)	0.3192 (2)	0.0177 (8)
C8	0.1201 (4)	0.8755 (4)	0.2195 (2)	0.0136 (7)
C9	0.1340 (5)	0.9975 (4)	0.1825 (2)	0.0192 (8)
H9	0.1618	1.0799	0.2072	0.023*
C10	0.1069 (5)	0.9982 (5)	0.1093 (2)	0.0239 (9)
H10	0.1154	1.0814	0.0841	0.029*
C11	0.0675 (5)	0.8778 (5)	0.0733 (2)	0.0235 (9)
H11	0.0511	0.878	0.0233	0.028*
C12	0.0521 (5)	0.7567 (5)	0.1102 (2)	0.0214 (9)
H12	0.0237	0.6745	0.0852	0.026*
C13	0.0776 (4)	0.7549 (4)	0.1828 (2)	0.0186 (8)
H13	0.0663	0.6718	0.2078	0.022*
C14	−0.0242 (4)	0.8745 (4)	0.3454 (2)	0.0156 (8)
C15	−0.1503 (5)	0.8706 (5)	0.2982 (2)	0.0206 (9)
H15	−0.1454	0.8667	0.2489	0.025*
C16	−0.2835 (5)	0.8724 (5)	0.3239 (3)	0.0261 (10)
H16	−0.37	0.8687	0.2922	0.031*
C17	−0.2900 (5)	0.8795 (5)	0.3957 (3)	0.0259 (10)
H17	−0.3812	0.882	0.4128	0.031*
C18	−0.1647 (5)	0.8830 (5)	0.4427 (2)	0.0236 (9)
H18	−0.17	0.8872	0.4919	0.028*
C19	−0.0315 (5)	0.8803 (5)	0.4177 (2)	0.0204 (8)
H19	0.0547	0.8824	0.4497	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Se1	0.0197 (2)	0.0211 (3)	0.0260 (3)	−0.00604 (17)	0.00179 (16)	−0.00448 (17)
Cl3	0.0239 (5)	0.0179 (5)	0.0317 (6)	0.0050 (4)	0.0049 (4)	0.0057 (4)
P1	0.0138 (5)	0.0119 (5)	0.0183 (5)	−0.0001 (4)	0.0032 (4)	0.0002 (4)
O1	0.0148 (13)	0.0164 (15)	0.0231 (14)	0.0027 (11)	0.0044 (11)	0.0033 (11)
O2	0.0193 (15)	0.0260 (17)	0.0286 (16)	0.0038 (13)	0.0079 (12)	0.0092 (13)
C1	0.0147 (18)	0.015 (2)	0.0198 (19)	−0.0007 (15)	0.0009 (15)	−0.0001 (15)
C2	0.0164 (19)	0.020 (2)	0.027 (2)	0.0034 (16)	0.0084 (16)	0.0015 (17)
C3	0.023 (2)	0.022 (2)	0.027 (2)	−0.0003 (18)	0.0119 (17)	0.0052 (18)
C4	0.0179 (19)	0.0130 (19)	0.024 (2)	−0.0018 (16)	−0.0004 (15)	0.0008 (16)
C5	0.0167 (19)	0.019 (2)	0.024 (2)	0.0048 (16)	0.0042 (15)	−0.0031 (16)
C6	0.019 (2)	0.022 (2)	0.0178 (19)	0.0028 (17)	0.0034 (15)	−0.0014 (16)
C7	0.0133 (18)	0.020 (2)	0.0196 (19)	0.0015 (16)	0.0013 (14)	−0.0012 (16)
C8	0.0096 (16)	0.0099 (18)	0.0217 (19)	0.0005 (14)	0.0036 (14)	0.0013 (15)
C9	0.020 (2)	0.0115 (19)	0.026 (2)	0.0035 (16)	0.0041 (16)	0.0015 (15)
C10	0.026 (2)	0.020 (2)	0.025 (2)	0.0035 (18)	0.0029 (17)	0.0077 (17)
C11	0.023 (2)	0.027 (2)	0.020 (2)	0.0013 (19)	0.0012 (16)	0.0019 (18)
C12	0.021 (2)	0.017 (2)	0.026 (2)	−0.0016 (17)	0.0017 (16)	−0.0032 (17)
C13	0.0181 (19)	0.0122 (19)	0.026 (2)	−0.0018 (16)	0.0039 (15)	−0.0005 (16)
C14	0.0144 (18)	0.0081 (17)	0.025 (2)	0.0001 (14)	0.0047 (15)	0.0018 (15)
C15	0.018 (2)	0.021 (2)	0.023 (2)	0.0001 (17)	0.0035 (16)	0.0026 (17)
C16	0.0127 (19)	0.030 (3)	0.036 (2)	0.0012 (18)	0.0030 (17)	0.007 (2)
C17	0.020 (2)	0.021 (2)	0.039 (3)	0.0026 (18)	0.0132 (18)	0.0050 (19)
C18	0.029 (2)	0.020 (2)	0.024 (2)	−0.0018 (18)	0.0112 (17)	−0.0012 (17)
C19	0.020 (2)	0.017 (2)	0.024 (2)	−0.0010 (17)	0.0035 (16)	−0.0006 (16)

Geometric parameters (Å, º) top

Se1—P1	2.0774 (11)	C9—C10	1.392 (6)
Cl3—C4	1.740 (4)	C9—H9	0.95
P1—O1	1.653 (3)	C10—C11	1.384 (7)
P1—C8	1.802 (4)	C10—H10	0.95
P1—C14	1.809 (4)	C11—C12	1.388 (6)
O1—C7	1.380 (5)	C11—H11	0.95
O2—C7	1.197 (5)	C12—C13	1.382 (6)
C1—C6	1.396 (6)	C12—H12	0.95
C1—C2	1.397 (6)	C13—H13	0.95
C1—C7	1.479 (6)	C14—C15	1.394 (6)
C2—C3	1.392 (6)	C14—C19	1.394 (6)
C2—H2	0.95	C15—C16	1.393 (6)
C3—C4	1.380 (6)	C15—H15	0.95
C3—H3	0.95	C16—C17	1.383 (7)
C4—C5	1.385 (6)	C16—H16	0.95
C5—C6	1.389 (6)	C17—C18	1.387 (7)
C5—H5	0.95	C17—H17	0.95
C6—H6	0.95	C18—C19	1.387 (6)
C8—C9	1.395 (6)	C18—H18	0.95
C8—C13	1.398 (6)	C19—H19	0.95

O1—P1—C8	105.05 (17)	C10—C9—H9	120
O1—P1—C14	98.28 (17)	C8—C9—H9	120
C8—P1—C14	106.94 (18)	C11—C10—C9	120.0 (4)
O1—P1—Se1	114.93 (11)	C11—C10—H10	120
C8—P1—Se1	115.52 (13)	C9—C10—H10	120
C14—P1—Se1	114.32 (14)	C10—C11—C12	120.1 (4)
C7—O1—P1	119.8 (3)	C10—C11—H11	119.9
C6—C1—C2	120.0 (4)	C12—C11—H11	119.9
C6—C1—C7	117.4 (4)	C13—C12—C11	120.4 (4)
C2—C1—C7	122.6 (4)	C13—C12—H12	119.8
C3—C2—C1	119.8 (4)	C11—C12—H12	119.8
C3—C2—H2	120.1	C12—C13—C8	119.9 (4)
C1—C2—H2	120.1	C12—C13—H13	120.1
C4—C3—C2	119.2 (4)	C8—C13—H13	120.1
C4—C3—H3	120.4	C15—C14—C19	120.2 (4)
C2—C3—H3	120.4	C15—C14—P1	120.9 (3)
C3—C4—C5	122.0 (4)	C19—C14—P1	118.8 (3)
C3—C4—Cl3	119.3 (3)	C16—C15—C14	119.4 (4)
C5—C4—Cl3	118.7 (3)	C16—C15—H15	120.3
C4—C5—C6	118.8 (4)	C14—C15—H15	120.3
C4—C5—H5	120.6	C17—C16—C15	120.1 (4)
C6—C5—H5	120.6	C17—C16—H16	119.9
C5—C6—C1	120.2 (4)	C15—C16—H16	119.9
C5—C6—H6	119.9	C16—C17—C18	120.6 (4)
C1—C6—H6	119.9	C16—C17—H17	119.7
O2—C7—O1	122.2 (4)	C18—C17—H17	119.7
O2—C7—C1	125.4 (4)	C19—C18—C17	119.8 (4)
O1—C7—C1	112.4 (3)	C19—C18—H18	120.1
C9—C8—C13	119.7 (4)	C17—C18—H18	120.1
C9—C8—P1	119.1 (3)	C18—C19—C14	119.9 (4)
C13—C8—P1	121.1 (3)	C18—C19—H19	120
C10—C9—C8	119.9 (4)	C14—C19—H19	120

C8—P1—O1—C7	65.5 (3)	Se1—P1—C8—C13	156.6 (3)
C14—P1—O1—C7	175.7 (3)	C13—C8—C9—C10	−0.7 (6)
Se1—P1—O1—C7	−62.6 (3)	P1—C8—C9—C10	−178.4 (3)
C6—C1—C2—C3	2.5 (7)	C8—C9—C10—C11	−0.5 (7)
C7—C1—C2—C3	−175.0 (4)	C9—C10—C11—C12	1.2 (7)
C1—C2—C3—C4	−1.5 (7)	C10—C11—C12—C13	−0.8 (7)
C2—C3—C4—C5	−1.3 (7)	C11—C12—C13—C8	−0.4 (6)
C2—C3—C4—Cl3	176.7 (4)	C9—C8—C13—C12	1.1 (6)
C3—C4—C5—C6	2.9 (7)	P1—C8—C13—C12	178.8 (3)
Cl3—C4—C5—C6	−175.0 (3)	O1—P1—C14—C15	−108.5 (4)
C4—C5—C6—C1	−1.9 (7)	C8—P1—C14—C15	0.1 (4)
C2—C1—C6—C5	−0.8 (7)	Se1—P1—C14—C15	129.3 (3)
C7—C1—C6—C5	176.8 (4)	O1—P1—C14—C19	73.5 (4)
P1—O1—C7—O2	−15.8 (6)	C8—P1—C14—C19	−177.9 (3)
P1—O1—C7—C1	164.5 (3)	Se1—P1—C14—C19	−48.7 (4)
C6—C1—C7—O2	−9.5 (7)	C19—C14—C15—C16	0.0 (7)
C2—C1—C7—O2	168.1 (5)	P1—C14—C15—C16	−178.0 (4)
C6—C1—C7—O1	170.3 (4)	C14—C15—C16—C17	0.6 (7)
C2—C1—C7—O1	−12.2 (6)	C15—C16—C17—C18	−0.9 (8)
O1—P1—C8—C9	−153.4 (3)	C16—C17—C18—C19	0.5 (7)
C14—P1—C8—C9	102.8 (3)	C17—C18—C19—C14	0.1 (7)
Se1—P1—C8—C9	−25.7 (4)	C15—C14—C19—C18	−0.3 (7)
O1—P1—C8—C13	28.9 (4)	P1—C14—C19—C18	177.6 (4)
C14—P1—C8—C13	−74.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.95	2.59	3.359 (6)	138

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₄ClO₂PSe
M_r	419.68
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	9.3390 (5), 9.7132 (5), 19.1353 (15)
β (°)	97.059 (6)
V (Å³)	1722.64 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.44
Crystal size (mm)	0.46 × 0.33 × 0.26

Data collection
Diffractometer	Oxford Diffraction KM-4-CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.325, 0.53
No. of measured, independent and observed [I > 2σ(I)] reflections	14128, 4158, 3376
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.162, 1.16
No. of reflections	4158
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.82, −0.56

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O2ⁱ	0.9500	2.5900	3.359 (6)	138.00

Symmetry code: (i) x−1, y, z.

Acknowledgements

JC and JP thank the Gdansk University of Technology for financial support (internal grant No. 014668 t. 005).

References

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