Acetonyltriphenyl­phospho­nium nitrate

Diop, T.; Diop, L.; Kučeráková, M.; Dušek, M.

doi:10.1107/S1600536813002110

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o303

doi:10.1107/S1600536813002110

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Acetonyltriphenylphosphonium nitrate

Tidiane Diop,^a ^* Libasse Diop,^a Monika Kučeráková ^b and Michal Dušek ^b

^aLaboratoire de Chimie Minerale et Analytique, Departement de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: tijchimia@yahoo.fr

(Received 9 December 2012; accepted 21 January 2013; online 31 January 2013)

Crystals of the title salt, C₂₁H₂₀OP⁺·NO₃⁻, are composed of acetonyltriphenylphosphonium cations and nitrate anions that mainly interact through electrostatic forces. The P atom in the cation has a slightly distorted tetrahedral environment, with C—P—C angles ranging from 104.79 (7) to 112.59 (6)°. The sum of O—N—O angles of the nitrate anion is 359.99°, reflecting its trigonal–planar character. C—H⋯O hydrogen bonds help to consolidate the crystal packing.

Related literature

For crystal structures containing triphenylphosphonium moieties, see: van der Sluis & Spek (1990 ); Boys et al. (1995 ); Zhang et al. (2004 ); Evans (2010 ); Kavitha et al. (2012 ).

Experimental

Crystal data

C₂₁H₂₀OP⁺·NO₃⁻
M_r = 381.4
Monoclinic, C 2/c
a = 14.0928 (5) Å
b = 12.6455 (3) Å
c = 21.2684 (6) Å
β = 90.667 (2)°
V = 3790.00 (19) Å³
Z = 8
Cu Kα radiation
μ = 1.51 mm⁻¹
T = 120 K
0.19 × 0.18 × 0.12 mm

Data collection

Agilent Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.271, T_max = 1
22035 measured reflections
3389 independent reflections
2969 reflections with I > 3σ(I)
R_int = 0.040

Refinement

R[F² > 3σ(F²)] = 0.033
wR(F²) = 0.094
S = 1.63
3389 reflections
250 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H1c5⋯O3ⁱ	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5—H3c5⋯O2ⁱⁱ	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7—H1c7⋯O3ⁱ	0.96	2.49	3.4365 (19)	167.90
C8—H1c8⋯O3	0.96	2.50	3.177 (2)	127.75
C10—H1c10⋯O2ⁱⁱ	0.96	2.49	3.3706 (19)	152.50
C15—H1c15⋯O1	0.96	2.36	3.1780 (19)	142.99
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813002110/wm2713sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002110/wm2713Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002110/wm2713Isup3.cml

checkCIF report

Comment top

Phosphonium salts [PR₄⁺, R = alkyl or aryl] are widely used as large cations to stabilize a variety of anonic species (Zhang et al., 2004; van der Sluis & Spek, 1990; Evans, 2010).

The title compound crystallizes with one phosphonium cation, C₂₁H₂₀OP⁺, and one nitrate anion in the asymmetric unit (Fig. 1). The P—C bond lengths within the cation [1.7947 (13), 1.7984 (14), 1.7992 (15) and 1.8024 (13) Å] are similar than those reported for related phosphonium salts like [1-(ethoxycarbonyl)-1-cyclopentyl]triphenylphosphonium bromide (Boys et al., 1995), or [3-(iodoacetamido)propyl]triphenylphosphonium tetraphenylborate (Evans, 2010) indicating that the presence of the acetonyl moiety has a negligible effect on the geometrical parameters. The C—P—C angles (range 104.79 (7) to 112.59 (6) °) indicate a slight angular distortion. The sum of the O—N—O angles [120.84 (14), 120.16 (14) and 118.99 (12) °] of the nitrate anion is 359.99°, reflecting its trigonal-planar geometry. Between the C₂₁H₂₀OP⁺ cations and the NO₃^- anions, the interactions are mainly of electrostatic nature. Such forces are also respondible for related salts like (3-chloropropyl)triphenylphosphonium bromide (Kavitha, 2012). The packing of the structure is shown in Fig. 2. Weak C—H···O hydrogen bonds (Table 1) help to consolidate the crystal packing.

Related literature top

For crystal structures containing triphenylphosphonium moieties, see: van der Sluis & Spek (1990); Boys et al. (1995); Zhang et al. (2004); Evans (2010); Kavitha et al. (2012).

Experimental top

All chemicals were purchased from Aldrich (Germany) and used without any further purification. Colourless crystals of the title compound, C₂₁H₂₀OP⁺^.NO₃^-, have been obtained by the addition of a solution of Pb(NO₃)₂ (0.46 g,1.4 mmol) in water to a solution of CH₃COCH₂P(C₆H₅)₃Cl (0.5 g, 1.4 mmol) in water. The precipitated PbCl₂ was filtered off. Regular crystals were grown after slow solvent evaporation within few days.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2006); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2006).

Figures top

	Fig. 1. The molecular entities of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound.

Acetonyltriphenylphosphonium nitrate top

Crystal data top

C₂₁H₂₀OP⁺·NO₃⁻	F(000) = 1600
M_r = 381.4	D_x = 1.336 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -C 2yc	Cell parameters from 12744 reflections
a = 14.0928 (5) Å	θ = 4.2–67.0°
b = 12.6455 (3) Å	µ = 1.51 mm⁻¹
c = 21.2684 (6) Å	T = 120 K
β = 90.667 (2)°	Polygon, colourless
V = 3790.00 (19) Å³	0.19 × 0.18 × 0.12 mm
Z = 8

Data collection top

Agilent Xcalibur diffractometer	3389 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2969 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.040
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 4.2°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −15→15
T_min = 0.271, T_max = 1	l = −25→24
22035 measured reflections

Refinement top

Refinement on F²	74 constraints
R[F² > 2σ(F²)] = 0.033	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	Weighting scheme based on measured s.u.'s w = 1/(σ²(I) + 0.0016I²)
S = 1.63	(Δ/σ)_max = 0.015
3389 reflections	Δρ_max = 0.27 e Å⁻³
250 parameters	Δρ_min = −0.24 e Å⁻³
2 restraints

Crystal data top

C₂₁H₂₀OP⁺·NO₃⁻	V = 3790.00 (19) Å³
M_r = 381.4	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 14.0928 (5) Å	µ = 1.51 mm⁻¹
b = 12.6455 (3) Å	T = 120 K
c = 21.2684 (6) Å	0.19 × 0.18 × 0.12 mm
β = 90.667 (2)°

Data collection top

Agilent Xcalibur diffractometer	3389 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2969 reflections with I > 3σ(I)
T_min = 0.271, T_max = 1	R_int = 0.040
22035 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.63	Δρ_max = 0.27 e Å⁻³
3389 reflections	Δρ_min = −0.24 e Å⁻³
250 parameters

Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
P1	0.77023 (2)	0.09776 (3)	0.113631 (14)	0.01755 (11)
O1	0.93221 (8)	−0.03291 (9)	0.16541 (5)	0.0296 (3)
O2	0.22566 (11)	0.26725 (9)	0.14746 (5)	0.0446 (4)
O3	0.30174 (9)	0.15360 (10)	0.20579 (6)	0.0406 (4)
O4	0.14881 (9)	0.15797 (11)	0.20713 (5)	0.0401 (4)
N1	0.22509 (10)	0.19384 (10)	0.18695 (5)	0.0268 (4)
C1	0.83285 (10)	0.21866 (11)	0.13029 (6)	0.0194 (4)
C2	0.81834 (10)	0.03489 (11)	0.04539 (6)	0.0206 (4)
C3	0.86270 (11)	−0.04050 (11)	0.19812 (6)	0.0227 (4)
C4	0.88403 (11)	−0.05841 (13)	−0.06351 (6)	0.0295 (5)
C5	0.76868 (10)	0.00921 (11)	0.18002 (6)	0.0208 (4)
C6	0.97263 (12)	0.31195 (13)	0.16513 (8)	0.0333 (5)
C7	0.59222 (11)	0.16606 (11)	0.14808 (7)	0.0258 (4)
C8	0.49814 (12)	0.19171 (12)	0.13750 (8)	0.0323 (5)
C9	0.64745 (10)	0.12851 (11)	0.09836 (6)	0.0214 (4)
C10	0.79251 (12)	−0.06863 (12)	0.03122 (6)	0.0275 (4)
C11	0.45787 (12)	0.17953 (13)	0.07799 (9)	0.0361 (5)
C12	0.91054 (11)	0.04412 (13)	−0.04893 (6)	0.0277 (4)
C13	0.87750 (11)	0.09150 (12)	0.00565 (6)	0.0229 (4)
C14	0.83609 (12)	0.40906 (12)	0.12938 (7)	0.0286 (5)
C15	0.92558 (11)	0.21760 (12)	0.15421 (7)	0.0267 (4)
C16	0.78818 (11)	0.31533 (11)	0.11762 (6)	0.0231 (4)
C17	0.51200 (13)	0.14219 (13)	0.02899 (8)	0.0353 (5)
C18	0.92784 (13)	0.40728 (13)	0.15289 (8)	0.0323 (5)
C19	0.82556 (13)	−0.11492 (13)	−0.02360 (7)	0.0320 (5)
C20	0.86235 (13)	−0.09946 (13)	0.25901 (7)	0.0314 (5)
C21	0.60690 (11)	0.11658 (12)	0.03874 (7)	0.0279 (4)
H1c4	0.90622	−0.090662	−0.101466	0.0354*
H1c5	0.7458 (12)	0.0463 (12)	0.2162 (5)	0.025*
H3c5	0.7248 (10)	−0.0467 (10)	0.1703 (8)	0.025*
H1c6	1.036543	0.311308	0.18125	0.04*
H1c7	0.619748	0.173886	0.189322	0.0309*
H1c8	0.460415	0.218052	0.171378	0.0387*
H1c10	0.7523	−0.107678	0.058995	0.033*
H1c11	0.392337	0.197082	0.070905	0.0433*
H1c12	0.951668	0.082514	−0.076422	0.0333*
H1c13	0.895387	0.162776	0.015848	0.0275*
H1c14	0.8054	0.475496	0.121157	0.0343*
H1c15	0.956584	0.151559	0.163037	0.032*
H1c16	0.724642	0.316673	0.100864	0.0277*
H1c17	0.483862	0.133891	−0.012037	0.0424*
H1c18	0.96073	0.472515	0.160779	0.0387*
H1c19	0.807881	−0.186217	−0.033893	0.0384*
H1c20	0.808354	−0.145686	0.260001	0.0377*
H2c20	0.919458	−0.140447	0.262926	0.0377*
H3c20	0.85903	−0.050131	0.293224	0.0377*
H1c21	0.64433	0.090806	0.004569	0.0334*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0193 (2)	0.01481 (19)	0.01853 (19)	0.00064 (12)	0.00178 (13)	−0.00047 (11)
O1	0.0281 (6)	0.0311 (6)	0.0297 (5)	0.0062 (4)	0.0058 (4)	0.0063 (4)
O2	0.0793 (10)	0.0237 (6)	0.0305 (6)	−0.0097 (6)	−0.0068 (6)	0.0070 (5)
O3	0.0302 (7)	0.0460 (7)	0.0457 (6)	−0.0026 (6)	0.0044 (5)	0.0129 (5)
O4	0.0328 (7)	0.0494 (8)	0.0381 (6)	0.0049 (6)	0.0030 (5)	0.0117 (5)
N1	0.0398 (8)	0.0197 (6)	0.0210 (6)	−0.0021 (5)	−0.0003 (5)	−0.0017 (4)
C1	0.0231 (7)	0.0170 (7)	0.0183 (6)	−0.0006 (5)	0.0028 (5)	−0.0008 (5)
C2	0.0220 (7)	0.0207 (7)	0.0191 (6)	0.0039 (5)	0.0000 (5)	0.0000 (5)
C3	0.0291 (8)	0.0157 (7)	0.0232 (6)	0.0018 (5)	0.0018 (5)	−0.0002 (5)
C4	0.0296 (8)	0.0387 (9)	0.0200 (6)	0.0109 (7)	−0.0019 (5)	−0.0057 (6)
C5	0.0254 (7)	0.0178 (7)	0.0195 (6)	0.0000 (5)	0.0041 (5)	0.0004 (5)
C6	0.0291 (9)	0.0282 (8)	0.0424 (8)	−0.0048 (7)	−0.0080 (6)	0.0019 (6)
C7	0.0238 (8)	0.0194 (7)	0.0342 (7)	−0.0016 (6)	0.0030 (6)	−0.0029 (6)
C8	0.0248 (8)	0.0221 (8)	0.0502 (9)	−0.0009 (6)	0.0068 (7)	−0.0014 (6)
C9	0.0207 (7)	0.0156 (7)	0.0280 (7)	−0.0028 (5)	−0.0001 (5)	0.0015 (5)
C10	0.0369 (9)	0.0225 (7)	0.0233 (7)	−0.0015 (6)	0.0032 (6)	−0.0020 (6)
C11	0.0211 (8)	0.0266 (8)	0.0604 (10)	−0.0010 (6)	−0.0050 (7)	0.0088 (7)
C12	0.0246 (8)	0.0372 (9)	0.0216 (6)	0.0068 (6)	0.0031 (5)	0.0044 (6)
C13	0.0226 (7)	0.0237 (8)	0.0226 (6)	0.0040 (6)	0.0002 (5)	0.0028 (5)
C14	0.0339 (9)	0.0175 (7)	0.0344 (7)	−0.0005 (6)	0.0013 (6)	0.0012 (6)
C15	0.0257 (8)	0.0209 (7)	0.0334 (7)	0.0011 (6)	−0.0021 (6)	0.0021 (6)
C16	0.0246 (8)	0.0211 (7)	0.0236 (6)	0.0012 (6)	0.0010 (5)	0.0007 (5)
C17	0.0311 (9)	0.0330 (9)	0.0415 (9)	−0.0042 (7)	−0.0112 (7)	0.0095 (7)
C18	0.0363 (9)	0.0219 (8)	0.0385 (8)	−0.0078 (6)	−0.0032 (7)	−0.0008 (6)
C19	0.0422 (10)	0.0263 (8)	0.0274 (7)	0.0034 (7)	−0.0024 (6)	−0.0078 (6)
C20	0.0351 (9)	0.0307 (9)	0.0284 (7)	0.0008 (7)	0.0002 (6)	0.0089 (6)
C21	0.0292 (8)	0.0256 (8)	0.0288 (7)	−0.0017 (6)	−0.0027 (6)	0.0041 (6)

Geometric parameters (Å, º) top

P1—C1	1.7984 (14)	C7—H1c7	0.96
P1—C2	1.7947 (13)	C8—C11	1.390 (2)
P1—C5	1.8024 (13)	C8—H1c8	0.96
P1—C9	1.7992 (15)	C9—C21	1.393 (2)
O1—C3	1.2120 (18)	C10—C19	1.390 (2)
O2—N1	1.2520 (16)	C10—H1c10	0.96
O3—N1	1.2554 (18)	C11—C17	1.382 (2)
O4—N1	1.2475 (18)	C11—H1c11	0.96
C1—C15	1.397 (2)	C12—C13	1.391 (2)
C1—C16	1.400 (2)	C12—H1c12	0.96
C2—C10	1.391 (2)	C13—H1c13	0.96
C2—C13	1.392 (2)	C14—C16	1.385 (2)
C3—C5	1.512 (2)	C14—C18	1.381 (2)
C3—C20	1.494 (2)	C14—H1c14	0.96
C4—C12	1.383 (2)	C15—H1c15	0.96
C4—C19	1.388 (2)	C16—H1c16	0.96
C4—H1c4	0.96	C17—C21	1.389 (2)
C5—H1c5	0.960 (13)	C17—H1c17	0.96
C5—H3c5	0.960 (13)	C18—H1c18	0.96
C6—C15	1.383 (2)	C19—H1c19	0.96
C6—C18	1.384 (2)	C20—H1c20	0.96
C6—H1c6	0.96	C20—H2c20	0.96
C7—C8	1.381 (2)	C20—H3c20	0.96
C7—C9	1.403 (2)	C21—H1c21	0.96

C1—P1—C2	110.29 (6)	C2—C10—C19	119.26 (14)
C1—P1—C5	112.59 (6)	C2—C10—H1c10	120.37
C1—P1—C9	108.70 (6)	C19—C10—H1c10	120.37
C2—P1—C5	111.49 (6)	C8—C11—C17	120.10 (16)
C2—P1—C9	108.74 (6)	C8—C11—H1c11	119.95
C5—P1—C9	104.79 (7)	C17—C11—H1c11	119.95
O2—N1—O3	120.16 (14)	C4—C12—C13	119.91 (14)
O2—N1—O4	120.84 (14)	C4—C12—H1c12	120.05
O3—N1—O4	118.99 (12)	C13—C12—H1c12	120.05
P1—C1—C15	121.23 (11)	C2—C13—C12	119.58 (14)
P1—C1—C16	119.07 (11)	C2—C13—H1c13	120.21
C15—C1—C16	119.69 (13)	C12—C13—H1c13	120.21
P1—C2—C10	119.46 (11)	C16—C14—C18	120.24 (14)
P1—C2—C13	119.85 (11)	C16—C14—H1c14	119.88
C10—C2—C13	120.63 (13)	C18—C14—H1c14	119.88
O1—C3—C5	122.18 (12)	C1—C15—C6	119.83 (14)
O1—C3—C20	123.22 (14)	C1—C15—H1c15	120.08
C5—C3—C20	114.60 (12)	C6—C15—H1c15	120.08
C12—C4—C19	120.40 (14)	C1—C16—C14	119.68 (14)
C12—C4—H1c4	119.8	C1—C16—H1c16	120.16
C19—C4—H1c4	119.8	C14—C16—H1c16	120.16
P1—C5—C3	116.05 (10)	C11—C17—C21	120.40 (16)
P1—C5—H1c5	109.4 (8)	C11—C17—H1c17	119.8
P1—C5—H3c5	107.6 (9)	C21—C17—H1c17	119.8
C3—C5—H1c5	107.5 (9)	C6—C18—C14	120.35 (15)
C3—C5—H3c5	108.0 (8)	C6—C18—H1c18	119.82
H1c5—C5—H3c5	108.1 (13)	C14—C18—H1c18	119.82
C15—C6—C18	120.20 (16)	C4—C19—C10	120.22 (15)
C15—C6—H1c6	119.9	C4—C19—H1c19	119.89
C18—C6—H1c6	119.9	C10—C19—H1c19	119.89
C8—C7—C9	119.78 (14)	C3—C20—H1c20	109.47
C8—C7—H1c7	120.11	C3—C20—H2c20	109.47
C9—C7—H1c7	120.11	C3—C20—H3c20	109.47
C7—C8—C11	120.24 (15)	H1c20—C20—H2c20	109.47
C7—C8—H1c8	119.88	H1c20—C20—H3c20	109.47
C11—C8—H1c8	119.88	H2c20—C20—H3c20	109.47
P1—C9—C7	118.54 (11)	C9—C21—C17	119.65 (14)
P1—C9—C21	121.64 (11)	C9—C21—H1c21	120.17
C7—C9—C21	119.83 (14)	C17—C21—H1c21	120.17

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1c5···O3ⁱ	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5—H3c5···O2ⁱⁱ	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7—H1c7···O3ⁱ	0.96	2.49	3.4365 (19)	167.90
C8—H1c8···O3	0.96	2.50	3.177 (2)	127.75
C10—H1c10···O2ⁱⁱ	0.96	2.49	3.3706 (19)	152.50
C15—H1c15···O1	0.96	2.36	3.1780 (19)	142.99

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀OP⁺·NO₃⁻
M_r	381.4
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	120
a, b, c (Å)	14.0928 (5), 12.6455 (3), 21.2684 (6)
β (°)	90.667 (2)
V (Å³)	3790.00 (19)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.19 × 0.18 × 0.12

Data collection
Diffractometer	Agilent Xcalibur diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.271, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	22035, 3389, 2969
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.094, 1.63
No. of reflections	3389
No. of parameters	250
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.24

Computer programs: CrysAlis PRO (Agilent, 2012), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2006), DIAMOND (Brandenburg & Putz, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H1c5···O3ⁱ	0.960 (13)	2.252 (13)	3.2053 (18)	172.1 (12)
C5—H3c5···O2ⁱⁱ	0.960 (13)	2.403 (12)	3.1936 (18)	139.4 (11)
C7—H1c7···O3ⁱ	0.96	2.49	3.4365 (19)	167.90
C8—H1c8···O3	0.96	2.50	3.177 (2)	127.75
C10—H1c10···O2ⁱⁱ	0.96	2.49	3.3706 (19)	152.50
C15—H1c15···O1	0.96	2.36	3.1780 (19)	142.99

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) x+1/2, y−1/2, z.

Acknowledgements

We acknowledge the Praemium Academiae project of the Academy of Sciences of the Czech Republic.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Boys, D., Araya-Maturana, R., González, O. & Manríquez, V. (1995). Acta Cryst. C51, 105–107. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Evans, C. (2010). Acta Cryst. E66, o384–o385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kavitha, C. N., Yathirajan, H. S., Dayananda, A. S., Gerber, T., Hosten, E. & Betz, R. (2012). Acta Cryst. E68, o3115. CSD CrossRef IUCr Journals Google Scholar
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790. Web of Science CrossRef CAS IUCr Journals Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics, Czech Academy of Sciences, Prague, Czech Republic. Google Scholar
Sluis, P. van der & Spek, A. L. (1990). Acta Cryst. C46, 2429–2431. CSD CrossRef Web of Science IUCr Journals Google Scholar
Zhang, X., Zhong, P., Hu, M., Lin, D. & Lin, J. (2004). Acta Cryst. E60, o1200–o1201. Web of Science CSD CrossRef IUCr Journals Google Scholar