(–)-(4R,5S)-4-Methyl-3-[2(S)-phenoxy­propion­yl]-5-phenyl­oxazolidin-2-one

Chavda, S.; Eames, J.; Motevalli, M.; Malatesti, N.

doi:10.1107/S1600536806031850

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 62| Part 9| September 2006| Pages o4043-o4045

https://doi.org/10.1107/S1600536806031850

(–)-(4R,5S)-4-Methyl-3-[2(S)-phenoxypropionyl]-5-phenyloxazolidin-2-one

Sameer Chavda,^a Jason Eames,^b ^* Majid Motevalli ^a and Nela Malatesti ^c

^aDepartment of Chemistry, Queen Mary, University of London, Mile End Road, London E1 4NS, England, ^bDepartment of Chemistry, University of Hull, Cottingham Road, Kingston-upon-Hull HU6 7RX, England, and ^cDepartment of Chemistry, J. J. Strossmayer University of Osijek, Trg Sv. Trojstva 3, Osijek 31000, Croatia
^*Correspondence e-mail: j.eames@hull.ac.uk

(Received 27 June 2006; accepted 12 August 2006; online 23 August 2006)

The title compound, C₁₉H₁₉NO₄, formed from enantiomerically pure (+)-(4R,5S)-4-methyl-5-phenyl-2-oxazolidinone and racemic 2-phenoxypropanoyl chloride, crystallises with Z′ = 2. The two carbonyl groups in each molecule are oriented anti to each other, while the two methyl groups are oriented syn to each other.

Comment

The title compound, (I), is the sixth in a series of structurally related compounds, introduced in our earlier report (Coumbarides, Eames et al., 2006a ). With R¹ = C₆H₅O, the reaction shown in that report yielded the anti–syn and syn–syn diastereomers in 44 and 45% yields, respectively. The syn–syn diastereomer was described previously (Coumbarides, Eames et al., 2006b ). The title compound, (I), is the anti–syn diastereomer.

Compound (I) contains two molecules in the asymmetric unit in the space group P2₁, displaying closely comparable conformations (Fig. 1). In line with our previous reports (Coumbarides, Eames et al., 2006a,b; Coumbarides, Dingjan et al., 2006 ; Chavda et al., 2006a ,b ), the carbonyl groups (C3A=O2A/C11A=O3A and C3B=O2B/C11B=O3B) are oriented anti to each other, with torsion angles O3—C11—N1—C3 = 176.5 (2) and 175.9 (2)° for molecules A and B, respectively. The two methyl groups (C4A/C19A and C4B/C19B) lie to the same side of the molecule. The principal distinction between the two independent molecules of (I) lies in the orientations of the phenoxypropionyl substituent with respect to the central portion of the molecule, with torsion angles O3—C11—C12—O4 = −25.6 (3) and −14.6 (3)° for molecules A and B, respectively. This subtle difference can be attributed to the influence of intermolecular interactions in the solid state. As observed in the phenylpropionyl derivative (Coumbarides, Eames et al., 2006a), adjacent molecules approach each other in a `side-on' manner (Fig. 2), and the shortest intermolecular contacts are C—H⋯O interactions (Table 1).

Figure 1
Two molecules in the asymmetric unit of (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted.

Figure 2
The crystal packing of (I)

viewed along the b axis. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted.

Experimental

The title compound was obtained from the same synthesis as the syn–syn diastereomer, as reported previously (Coumbarides, Eames et al., 2006b). The anti–syn diastereomer, (I), was obtained as colourless crystals {4.03 g, 44% yield, m.p. 362–365 K, R_F 0.61 [light petroleum (b.p 313–333 K)/diethyl ether, 1:1]}. Spectroscopic analysis: [α]²²_D = −35.5 (CHCl₃, 293 K, concentration 2.0 g per 100 ml); IR (CHCl₃, ν_max, cm⁻¹): 1776 (C=O), 1714 (C=O); ¹H NMR (270 MHz, CDCl₃): δ 7.45–7.21 (7H, m, 7 × CH; Ph_a and Ph_b), 6.97–6.86 (3H, m, 3 × CH; Ph_a or Ph_b), 5.94 (1H, q, J = 6.7 Hz, PhOCH), 5.75 (1H, d, J = 7.4 Hz, PhCHO), 4.81 (1H, m, CHN), 1.66 (3H, d, J = 6.7 Hz, CH₃CHCO), 0.89 (3H, d, J = 6.6 Hz, CH₃CHN); ¹³C NMR (67.9 MHz, CDCl₃, δ, p.p.m.): 172.0 (NC=O), 157.4 (i-CO; Ph), 152.8 (OC=O), 133.1 (i-C; Ph), 129.7, 129.0, 128.9, 125.7, 121.6, 115.1 (6 × CH; Ph_a and Ph_b), 79.8 (PhCHO), 71.8 (PhOCH), 54.7 (CHN), 18.3 (CH₃), 14.5 (CH₃); found: MH⁺ 326.1393; C₁₉H₂₀NO₄ requires 326.1392.

Crystal data

C₁₉H₁₉NO₄
M_r = 325.35
Monoclinic, P 2₁
a = 11.268 (7) Å
b = 10.493 (5) Å
c = 15.008 (9) Å
β = 102.96 (4)°
V = 1729.3 (17) Å³
Z = 4
D_x = 1.250 Mg m⁻³
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 160 (2) K
Block, colourless
0.44 × 0.22 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
ω/2θ scans
Absorption correction: none
8490 measured reflections
3223 independent reflections
2662 reflections with I > 2σ(I)
R_int = 0.020
θ_max = 25.0°
2 standard reflections every 100 reflections intensity decay: 2%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.067
S = 1.01
3223 reflections
438 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0293P)² + 0.3025P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0167 (13)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1A—H1A⋯O3B	1.00	2.61	3.373 (3)	133
C1B—H1B⋯O3A	1.00	2.57	3.568 (3)	174
C18A—H18A⋯O4Bⁱ	0.95	2.52	3.445 (4)	165
C18B—H18B⋯O4Aⁱⁱ	0.95	2.69	3.564 (4)	154
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms, with C—H = 0.95–1.00 Å and U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). The methyl groups were allowed to rotate about their local threefold axes. In the absence of significant anomalous scattering effects, the few measured Friedel pairs have been merged. The absolute configuration is assigned on the basis of the known configuration of the starting material (Coumbarides, Eames et al., 2006a).

Data collection: CAD-4-PC Software (Enraf–Nonius, 1994 ); cell refinement: CAD-4-PC Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536806031850/bi2033sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536806031850/bi2033Isup2.hkl

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1994); cell refinement: CAD-4-PC Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(-)-(4R,5S)-4-Methyl-3-[2(S)-phenoxypropionyl]- 5-phenyloxazolidin-2-one top

Crystal data top

C₁₉H₁₉NO₄	F(000) = 688
M_r = 325.35	D_x = 1.250 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 25 reflections
a = 11.268 (7) Å	θ = 9.3–12.1°
b = 10.493 (5) Å	µ = 0.09 mm⁻¹
c = 15.008 (9) Å	T = 160 K
β = 102.96 (4)°	Block, colourless
V = 1729.3 (17) Å³	0.44 × 0.22 × 0.20 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.020
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 1.9°
Graphite monochromator	h = −13→13
ω/2θ scans	k = −12→10
8490 measured reflections	l = −17→17
3223 independent reflections	2 standard reflections every 100 reflections
2662 reflections with I > 2σ(I)	intensity decay: 2%

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0293P)² + 0.3025P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.067	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.13 e Å⁻³
3223 reflections	Δρ_min = −0.14 e Å⁻³
438 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0167 (13)
Primary atom site location: structure-invariant direct methods	Absolute structure: assigned on the basis of known starting material
Secondary atom site location: difference Fourier map

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 > 2σ(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
C1A	0.8590 (2)	0.7252 (2)	0.54614 (16)	0.0319 (6)
H1A	0.8515	0.6363	0.5682	0.038*
C2A	0.7607 (2)	0.8113 (2)	0.56925 (17)	0.0316 (6)
H2A	0.7433	0.7824	0.6285	0.038*
C3A	0.9406 (2)	0.9171 (3)	0.61434 (17)	0.0331 (6)
C4A	0.8647 (3)	0.7257 (3)	0.44639 (17)	0.0457 (7)
H4A	0.7937	0.6806	0.4104	0.069*
H4B	0.9393	0.6828	0.4393	0.069*
H4C	0.8647	0.8138	0.4248	0.069*
C5A	0.6427 (2)	0.8218 (3)	0.49987 (17)	0.0335 (6)
C6A	0.6187 (3)	0.9201 (3)	0.43665 (18)	0.0418 (7)
H6A	0.6786	0.9833	0.4352	0.050*
C7A	0.5059 (3)	0.9253 (3)	0.37521 (19)	0.0495 (8)
H7A	0.4884	0.9933	0.3325	0.059*
C8A	0.4199 (3)	0.8328 (3)	0.3761 (2)	0.0513 (8)
H8A	0.3428	0.8379	0.3346	0.062*
C9A	0.4449 (3)	0.7325 (3)	0.4367 (2)	0.0499 (8)
H9A	0.3862	0.6672	0.4357	0.060*
C10A	0.5557 (2)	0.7274 (3)	0.49909 (17)	0.0417 (7)
H10A	0.5725	0.6591	0.5416	0.050*
C11A	1.0786 (2)	0.7267 (3)	0.62787 (17)	0.0350 (6)
C12A	1.1896 (2)	0.8077 (3)	0.66833 (18)	0.0385 (7)
H12A	1.1671	0.8796	0.7050	0.046*
C13A	1.2699 (2)	0.7019 (2)	0.81044 (18)	0.0356 (6)
C14A	1.1665 (2)	0.7249 (3)	0.84300 (18)	0.0357 (6)
H14A	1.0964	0.7617	0.8044	0.043*
C15A	1.1664 (3)	0.6934 (3)	0.93299 (19)	0.0419 (7)
H15A	1.0958	0.7094	0.9560	0.050*
C16A	1.2674 (3)	0.6392 (3)	0.98927 (19)	0.0481 (8)
H16A	1.2665	0.6174	1.0506	0.058*
C17A	1.3694 (3)	0.6170 (3)	0.9555 (2)	0.0509 (8)
H17A	1.4393	0.5800	0.9941	0.061*
C18A	1.3717 (2)	0.6475 (3)	0.8669 (2)	0.0438 (7)
H18A	1.4427	0.6313	0.8444	0.053*
C19A	1.2426 (3)	0.8579 (4)	0.5903 (2)	0.0593 (9)
H19A	1.3156	0.9084	0.6153	0.089*
H19B	1.1821	0.9114	0.5501	0.089*
H19C	1.2642	0.7860	0.5553	0.089*
N1A	0.96725 (18)	0.78883 (19)	0.60150 (13)	0.0305 (5)
O1A	0.82054 (15)	0.93517 (17)	0.58309 (11)	0.0348 (4)
O2A	1.00899 (18)	1.00028 (19)	0.64643 (14)	0.0451 (5)
O3A	1.08465 (17)	0.61293 (19)	0.61517 (14)	0.0444 (5)
O4A	1.28192 (15)	0.73015 (19)	0.72346 (13)	0.0426 (5)
C1B	1.0157 (2)	0.3999 (2)	0.78187 (16)	0.0285 (5)
H1B	1.0282	0.4597	0.7329	0.034*
C2B	1.1357 (2)	0.3824 (2)	0.85379 (16)	0.0271 (5)
H2B	1.1861	0.4611	0.8547	0.033*
C3B	0.9894 (2)	0.4373 (2)	0.93148 (16)	0.0272 (5)
C4B	0.9561 (2)	0.2784 (3)	0.73972 (18)	0.0382 (6)
H4D	0.9424	0.2214	0.7882	0.057*
H4E	1.0094	0.2363	0.7053	0.057*
H4F	0.8780	0.2987	0.6984	0.057*
C5B	1.2131 (2)	0.2691 (2)	0.84494 (16)	0.0268 (5)
C6B	1.1944 (2)	0.1511 (2)	0.88184 (17)	0.0323 (6)
H6B	1.1307	0.1404	0.9133	0.039*
C7B	1.2689 (2)	0.0491 (3)	0.87271 (18)	0.0389 (6)
H7B	1.2567	−0.0310	0.8987	0.047*
C8B	1.3605 (3)	0.0633 (3)	0.82617 (19)	0.0416 (7)
H8B	1.4109	−0.0072	0.8197	0.050*
C9B	1.3792 (3)	0.1801 (3)	0.7888 (2)	0.0444 (7)
H9B	1.4420	0.1900	0.7564	0.053*
C10B	1.3060 (2)	0.2825 (3)	0.79896 (18)	0.0364 (6)
H10B	1.3196	0.3630	0.7740	0.044*
C11B	0.8321 (2)	0.5233 (2)	0.79965 (16)	0.0274 (5)
C12B	0.7449 (2)	0.5565 (3)	0.86101 (17)	0.0311 (6)
H12B	0.7897	0.5979	0.9188	0.037*
C13B	0.6818 (2)	0.7632 (2)	0.79734 (16)	0.0285 (6)
C14B	0.7941 (2)	0.8189 (3)	0.83231 (17)	0.0354 (6)
H14B	0.8579	0.7710	0.8696	0.043*
C15B	0.8120 (2)	0.9456 (3)	0.81206 (18)	0.0401 (7)
H15B	0.8887	0.9846	0.8358	0.048*
C16B	0.7199 (2)	1.0154 (3)	0.75805 (17)	0.0393 (7)
H16B	0.7330	1.1019	0.7443	0.047*
C17B	0.6082 (2)	0.9585 (3)	0.72391 (18)	0.0365 (6)
H17B	0.5444	1.0066	0.6868	0.044*
C18B	0.5883 (2)	0.8326 (3)	0.74319 (17)	0.0339 (6)
H18B	0.5114	0.7941	0.7196	0.041*
C19B	0.6798 (2)	0.4372 (3)	0.88171 (19)	0.0416 (7)
H19D	0.6253	0.4589	0.9219	0.062*
H19E	0.7399	0.3745	0.9120	0.062*
H19F	0.6322	0.4012	0.8245	0.062*
N1B	0.94126 (17)	0.46148 (19)	0.83903 (12)	0.0266 (5)
O1B	1.09520 (14)	0.37535 (16)	0.93983 (10)	0.0299 (4)
O2B	0.94664 (15)	0.46410 (18)	0.99534 (11)	0.0359 (4)
O3B	0.80738 (16)	0.54245 (18)	0.71840 (11)	0.0367 (4)
O4B	0.65259 (14)	0.63842 (17)	0.81217 (12)	0.0336 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1A	0.0374 (13)	0.0248 (14)	0.0319 (13)	0.0009 (11)	0.0041 (11)	−0.0011 (11)
C2A	0.0384 (14)	0.0294 (15)	0.0275 (13)	0.0002 (12)	0.0083 (10)	−0.0005 (11)
C3A	0.0399 (15)	0.0279 (15)	0.0323 (13)	0.0002 (13)	0.0101 (12)	0.0003 (11)
C4A	0.0543 (17)	0.0488 (19)	0.0348 (15)	0.0156 (15)	0.0118 (13)	−0.0043 (14)
C5A	0.0371 (14)	0.0350 (15)	0.0296 (13)	0.0077 (12)	0.0102 (11)	−0.0040 (11)
C6A	0.0489 (16)	0.0362 (17)	0.0392 (15)	0.0063 (14)	0.0074 (13)	−0.0031 (13)
C7A	0.0586 (18)	0.0431 (18)	0.0402 (16)	0.0163 (16)	−0.0027 (13)	−0.0040 (14)
C8A	0.0396 (16)	0.063 (2)	0.0456 (17)	0.0103 (16)	−0.0024 (13)	−0.0122 (16)
C9A	0.0392 (16)	0.062 (2)	0.0486 (17)	−0.0055 (15)	0.0110 (14)	−0.0136 (17)
C10A	0.0449 (16)	0.0462 (18)	0.0354 (14)	−0.0016 (14)	0.0120 (12)	−0.0003 (13)
C11A	0.0405 (15)	0.0345 (18)	0.0332 (14)	0.0039 (13)	0.0154 (11)	0.0094 (12)
C12A	0.0340 (14)	0.0377 (17)	0.0433 (15)	0.0011 (12)	0.0080 (12)	0.0137 (13)
C13A	0.0354 (14)	0.0266 (15)	0.0443 (16)	−0.0061 (12)	0.0077 (12)	0.0028 (12)
C14A	0.0368 (15)	0.0269 (14)	0.0431 (15)	−0.0036 (12)	0.0086 (12)	−0.0018 (12)
C15A	0.0534 (17)	0.0281 (16)	0.0466 (17)	−0.0082 (13)	0.0164 (14)	−0.0132 (13)
C16A	0.066 (2)	0.0400 (19)	0.0352 (15)	−0.0138 (16)	0.0052 (14)	−0.0049 (13)
C17A	0.0505 (18)	0.048 (2)	0.0459 (18)	−0.0082 (16)	−0.0063 (14)	0.0062 (15)
C18A	0.0317 (14)	0.0439 (18)	0.0532 (18)	−0.0043 (13)	0.0037 (13)	0.0060 (14)
C19A	0.0462 (18)	0.070 (2)	0.063 (2)	−0.0015 (16)	0.0161 (16)	0.0254 (18)
N1A	0.0323 (11)	0.0244 (12)	0.0354 (11)	0.0024 (9)	0.0086 (9)	0.0018 (9)
O1A	0.0389 (10)	0.0283 (10)	0.0368 (10)	0.0029 (8)	0.0075 (8)	−0.0058 (8)
O2A	0.0461 (11)	0.0287 (11)	0.0581 (12)	−0.0046 (9)	0.0067 (9)	−0.0042 (9)
O3A	0.0464 (11)	0.0314 (12)	0.0556 (12)	0.0092 (9)	0.0119 (9)	0.0022 (9)
O4A	0.0321 (9)	0.0500 (13)	0.0469 (11)	0.0053 (9)	0.0113 (8)	0.0172 (9)
C1B	0.0321 (13)	0.0260 (14)	0.0297 (12)	0.0025 (11)	0.0119 (10)	0.0006 (10)
C2B	0.0289 (13)	0.0255 (14)	0.0286 (12)	−0.0026 (10)	0.0102 (10)	−0.0006 (10)
C3B	0.0282 (12)	0.0232 (13)	0.0298 (13)	−0.0006 (11)	0.0058 (10)	0.0000 (10)
C4B	0.0368 (14)	0.0369 (16)	0.0386 (14)	0.0012 (12)	0.0035 (11)	−0.0094 (12)
C5B	0.0251 (12)	0.0261 (14)	0.0290 (12)	0.0016 (10)	0.0052 (10)	−0.0021 (10)
C6B	0.0354 (14)	0.0296 (15)	0.0335 (14)	−0.0027 (12)	0.0111 (11)	0.0003 (11)
C7B	0.0486 (16)	0.0257 (15)	0.0407 (15)	0.0041 (13)	0.0065 (12)	0.0004 (12)
C8B	0.0420 (15)	0.0344 (17)	0.0476 (16)	0.0128 (13)	0.0085 (13)	−0.0068 (13)
C9B	0.0395 (16)	0.0451 (19)	0.0546 (17)	0.0038 (13)	0.0231 (13)	−0.0010 (14)
C10B	0.0377 (15)	0.0302 (15)	0.0447 (15)	0.0004 (12)	0.0165 (12)	0.0011 (12)
C11B	0.0294 (13)	0.0229 (14)	0.0286 (13)	−0.0008 (10)	0.0036 (10)	0.0016 (10)
C12B	0.0302 (13)	0.0310 (15)	0.0314 (13)	0.0073 (11)	0.0058 (10)	0.0050 (11)
C13B	0.0302 (13)	0.0290 (15)	0.0288 (12)	0.0045 (11)	0.0121 (10)	−0.0001 (11)
C14B	0.0357 (14)	0.0390 (17)	0.0295 (13)	0.0041 (13)	0.0029 (11)	−0.0006 (12)
C15B	0.0423 (15)	0.0375 (17)	0.0388 (15)	−0.0037 (14)	0.0052 (12)	−0.0044 (13)
C16B	0.0507 (17)	0.0329 (16)	0.0368 (15)	0.0036 (13)	0.0148 (13)	−0.0011 (12)
C17B	0.0350 (14)	0.0352 (17)	0.0431 (15)	0.0122 (13)	0.0165 (11)	0.0092 (13)
C18B	0.0270 (13)	0.0380 (17)	0.0384 (14)	0.0086 (12)	0.0109 (11)	0.0053 (12)
C19B	0.0380 (15)	0.0421 (18)	0.0454 (16)	0.0046 (14)	0.0111 (12)	0.0152 (14)
N1B	0.0298 (10)	0.0259 (12)	0.0247 (10)	0.0025 (9)	0.0073 (8)	−0.0012 (8)
O1B	0.0310 (9)	0.0327 (10)	0.0268 (9)	0.0056 (8)	0.0083 (7)	−0.0004 (7)
O2B	0.0396 (10)	0.0432 (11)	0.0272 (9)	0.0085 (9)	0.0121 (8)	0.0003 (8)
O3B	0.0414 (10)	0.0384 (11)	0.0293 (10)	0.0078 (9)	0.0059 (8)	0.0060 (8)
O4B	0.0281 (9)	0.0305 (10)	0.0417 (10)	0.0045 (8)	0.0069 (8)	0.0081 (8)

Geometric parameters (Å, º) top

C1A—N1A	1.472 (3)	C1B—N1B	1.476 (3)
C1A—C4A	1.513 (4)	C1B—C4B	1.512 (4)
C1A—C2A	1.528 (4)	C1B—C2B	1.540 (3)
C1A—H1A	1.000	C1B—H1B	1.000
C2A—O1A	1.457 (3)	C2B—O1B	1.465 (3)
C2A—C5A	1.498 (4)	C2B—C5B	1.498 (3)
C2A—H2A	1.000	C2B—H2B	1.0000
C3A—O2A	1.192 (3)	C3B—O2B	1.199 (3)
C3A—O1A	1.343 (3)	C3B—O1B	1.339 (3)
C3A—N1A	1.401 (4)	C3B—N1B	1.395 (3)
C4A—H4A	0.980	C4B—H4D	0.980
C4A—H4B	0.980	C4B—H4E	0.980
C4A—H4C	0.980	C4B—H4F	0.980
C5A—C6A	1.387 (4)	C5B—C10B	1.384 (4)
C5A—C10A	1.392 (4)	C5B—C6B	1.391 (4)
C6A—C7A	1.394 (4)	C6B—C7B	1.385 (4)
C6A—H6A	0.950	C6B—H6B	0.9500
C7A—C8A	1.374 (5)	C7B—C8B	1.378 (4)
C7A—H7A	0.950	C7B—H7B	0.950
C8A—C9A	1.378 (5)	C8B—C9B	1.384 (4)
C8A—H8A	0.950	C8B—H8B	0.950
C9A—C10A	1.384 (4)	C9B—C10B	1.383 (4)
C9A—H9A	0.950	C9B—H9B	0.950
C10A—H10A	0.950	C10B—H10B	0.950
C11A—O3A	1.213 (3)	C11B—O3B	1.205 (3)
C11A—N1A	1.390 (3)	C11B—N1B	1.399 (3)
C11A—C12A	1.522 (4)	C11B—C12B	1.529 (3)
C12A—O4A	1.429 (3)	C12B—O4B	1.420 (3)
C12A—C19A	1.522 (4)	C12B—C19B	1.518 (4)
C12A—H12A	1.000	C12B—H12B	1.000
C13A—O4A	1.375 (3)	C13B—O4B	1.380 (3)
C13A—C14A	1.382 (4)	C13B—C14B	1.386 (4)
C13A—C18A	1.387 (4)	C13B—C18B	1.384 (3)
C14A—C15A	1.391 (4)	C14B—C15B	1.389 (4)
C14A—H14A	0.950	C14B—H14B	0.950
C15A—C16A	1.379 (4)	C15B—C16B	1.375 (4)
C15A—H15A	0.950	C15B—H15B	0.950
C16A—C17A	1.376 (4)	C16B—C17B	1.384 (4)
C16A—H16A	0.950	C16B—H16B	0.950
C17A—C18A	1.374 (4)	C17B—C18B	1.381 (4)
C17A—H17A	0.950	C17B—H17B	0.950
C18A—H18A	0.950	C18B—H18B	0.950
C19A—H19A	0.980	C19B—H19D	0.980
C19A—H19B	0.980	C19B—H19E	0.980
C19A—H19C	0.980	C19B—H19F	0.980

N1A—C1A—C4A	110.1 (2)	N1B—C1B—C4B	110.8 (2)
N1A—C1A—C2A	98.90 (19)	N1B—C1B—C2B	99.74 (18)
C4A—C1A—C2A	114.6 (2)	C4B—C1B—C2B	115.5 (2)
N1A—C1A—H1A	110.9	N1B—C1B—H1B	110.1
C4A—C1A—H1A	110.9	C4B—C1B—H1B	110.1
C2A—C1A—H1A	110.9	C2B—C1B—H1B	110.1
O1A—C2A—C5A	110.1 (2)	O1B—C2B—C5B	109.91 (19)
O1A—C2A—C1A	102.94 (19)	O1B—C2B—C1B	103.03 (18)
C5A—C2A—C1A	117.5 (2)	C5B—C2B—C1B	118.0 (2)
O1A—C2A—H2A	108.7	O1B—C2B—H2B	108.5
C5A—C2A—H2A	108.7	C5B—C2B—H2B	108.5
C1A—C2A—H2A	108.7	C1B—C2B—H2B	108.5
O2A—C3A—O1A	123.2 (3)	O2B—C3B—O1B	123.2 (2)
O2A—C3A—N1A	128.3 (2)	O2B—C3B—N1B	128.0 (2)
O1A—C3A—N1A	108.5 (2)	O1B—C3B—N1B	108.71 (19)
C1A—C4A—H4A	109.5	C1B—C4B—H4D	109.5
C1A—C4A—H4B	109.5	C1B—C4B—H4E	109.5
H4A—C4A—H4B	109.5	H4D—C4B—H4E	109.5
C1A—C4A—H4C	109.5	C1B—C4B—H4F	109.5
H4A—C4A—H4C	109.5	H4D—C4B—H4F	109.5
H4B—C4A—H4C	109.5	H4E—C4B—H4F	109.5
C6A—C5A—C10A	119.7 (2)	C10B—C5B—C6B	119.2 (2)
C6A—C5A—C2A	122.4 (2)	C10B—C5B—C2B	118.9 (2)
C10A—C5A—C2A	117.9 (2)	C6B—C5B—C2B	121.9 (2)
C5A—C6A—C7A	119.4 (3)	C7B—C6B—C5B	119.9 (2)
C5A—C6A—H6A	120.3	C7B—C6B—H6B	120.0
C7A—C6A—H6A	120.3	C5B—C6B—H6B	120.0
C8A—C7A—C6A	120.4 (3)	C8B—C7B—C6B	120.4 (3)
C8A—C7A—H7A	119.8	C8B—C7B—H7B	119.8
C6A—C7A—H7A	119.8	C6B—C7B—H7B	119.8
C7A—C8A—C9A	120.4 (3)	C7B—C8B—C9B	120.0 (3)
C7A—C8A—H8A	119.8	C7B—C8B—H8B	120.0
C9A—C8A—H8A	119.8	C9B—C8B—H8B	120.0
C8A—C9A—C10A	119.7 (3)	C8B—C9B—C10B	119.6 (3)
C8A—C9A—H9A	120.1	C8B—C9B—H9B	120.2
C10A—C9A—H9A	120.1	C10B—C9B—H9B	120.2
C9A—C10A—C5A	120.3 (3)	C5B—C10B—C9B	120.8 (3)
C9A—C10A—H10A	119.8	C5B—C10B—H10B	119.6
C5A—C10A—H10A	119.8	C9B—C10B—H10B	119.6
O3A—C11A—N1A	119.7 (3)	O3B—C11B—N1B	119.1 (2)
O3A—C11A—C12A	122.8 (2)	O3B—C11B—C12B	122.5 (2)
N1A—C11A—C12A	117.4 (2)	N1B—C11B—C12B	118.3 (2)
O4A—C12A—C11A	109.9 (2)	O4B—C12B—C19B	105.83 (19)
O4A—C12A—C19A	106.4 (2)	O4B—C12B—C11B	108.79 (19)
C11A—C12A—C19A	108.4 (2)	C19B—C12B—C11B	109.9 (2)
O4A—C12A—H12A	110.7	O4B—C12B—H12B	110.7
C11A—C12A—H12A	110.7	C19B—C12B—H12B	110.7
C19A—C12A—H12A	110.7	C11B—C12B—H12B	110.7
O4A—C13A—C14A	124.6 (2)	O4B—C13B—C14B	124.7 (2)
O4A—C13A—C18A	115.1 (2)	O4B—C13B—C18B	114.6 (2)
C14A—C13A—C18A	120.2 (3)	C14B—C13B—C18B	120.7 (2)
C13A—C14A—C15A	119.1 (3)	C13B—C14B—C15B	119.1 (3)
C13A—C14A—H14A	120.5	C13B—C14B—H14B	120.5
C15A—C14A—H14A	120.5	C15B—C14B—H14B	120.5
C16A—C15A—C14A	120.9 (3)	C16B—C15B—C14B	120.8 (3)
C16A—C15A—H15A	119.6	C16B—C15B—H15B	119.6
C14A—C15A—H15A	119.6	C14B—C15B—H15B	119.6
C17A—C16A—C15A	119.1 (3)	C15B—C16B—C17B	119.4 (3)
C17A—C16A—H16A	120.4	C15B—C16B—H16B	120.3
C15A—C16A—H16A	120.4	C17B—C16B—H16B	120.3
C18A—C17A—C16A	121.1 (3)	C18B—C17B—C16B	120.8 (2)
C18A—C17A—H17A	119.5	C18B—C17B—H17B	119.6
C16A—C17A—H17A	119.5	C16B—C17B—H17B	119.6
C17A—C18A—C13A	119.6 (3)	C17B—C18B—C13B	119.2 (3)
C17A—C18A—H18A	120.2	C17B—C18B—H18B	120.4
C13A—C18A—H18A	120.2	C13B—C18B—H18B	120.4
C12A—C19A—H19A	109.5	C12B—C19B—H19D	109.5
C12A—C19A—H19B	109.5	C12B—C19B—H19E	109.5
H19A—C19A—H19B	109.5	H19D—C19B—H19E	109.5
C12A—C19A—H19C	109.5	C12B—C19B—H19F	109.5
H19A—C19A—H19C	109.5	H19D—C19B—H19F	109.5
H19B—C19A—H19C	109.5	H19E—C19B—H19F	109.5
C11A—N1A—C3A	128.2 (2)	C3B—N1B—C11B	127.83 (19)
C11A—N1A—C1A	121.9 (2)	C3B—N1B—C1B	110.69 (18)
C3A—N1A—C1A	109.7 (2)	C11B—N1B—C1B	121.20 (19)
C3A—O1A—C2A	108.74 (19)	C3B—O1B—C2B	109.88 (18)
C13A—O4A—C12A	117.3 (2)	C13B—O4B—C12B	118.93 (19)

N1A—C1A—C2A—O1A	31.9 (2)	N1B—C1B—C2B—O1B	26.6 (2)
C4A—C1A—C2A—O1A	−85.1 (3)	C4B—C1B—C2B—O1B	−92.1 (2)
N1A—C1A—C2A—C5A	153.1 (2)	N1B—C1B—C2B—C5B	147.9 (2)
C4A—C1A—C2A—C5A	36.0 (3)	C4B—C1B—C2B—C5B	29.2 (3)
O1A—C2A—C5A—C6A	21.5 (3)	O1B—C2B—C5B—C10B	−148.3 (2)
C1A—C2A—C5A—C6A	−95.9 (3)	C1B—C2B—C5B—C10B	94.1 (3)
O1A—C2A—C5A—C10A	−159.5 (2)	O1B—C2B—C5B—C6B	31.5 (3)
C1A—C2A—C5A—C10A	83.2 (3)	C1B—C2B—C5B—C6B	−86.2 (3)
C10A—C5A—C6A—C7A	2.2 (4)	C10B—C5B—C6B—C7B	0.4 (4)
C2A—C5A—C6A—C7A	−178.7 (2)	C2B—C5B—C6B—C7B	−179.4 (2)
C5A—C6A—C7A—C8A	−1.2 (4)	C5B—C6B—C7B—C8B	−0.9 (4)
C6A—C7A—C8A—C9A	−1.1 (5)	C6B—C7B—C8B—C9B	0.5 (4)
C7A—C8A—C9A—C10A	2.2 (4)	C7B—C8B—C9B—C10B	0.4 (4)
C8A—C9A—C10A—C5A	−1.1 (4)	C6B—C5B—C10B—C9B	0.5 (4)
C6A—C5A—C10A—C9A	−1.1 (4)	C2B—C5B—C10B—C9B	−179.7 (2)
C2A—C5A—C10A—C9A	179.8 (2)	C8B—C9B—C10B—C5B	−0.9 (4)
O3A—C11A—C12A—O4A	−25.6 (3)	O3B—C11B—C12B—O4B	−14.6 (3)
N1A—C11A—C12A—O4A	157.0 (2)	N1B—C11B—C12B—O4B	169.3 (2)
O3A—C11A—C12A—C19A	90.2 (3)	O3B—C11B—C12B—C19B	100.8 (3)
N1A—C11A—C12A—C19A	−87.1 (3)	N1B—C11B—C12B—C19B	−75.3 (3)
O4A—C13A—C14A—C15A	−179.2 (2)	O4B—C13B—C14B—C15B	179.8 (2)
C18A—C13A—C14A—C15A	0.4 (4)	C18B—C13B—C14B—C15B	−0.2 (4)
C13A—C14A—C15A—C16A	−0.4 (4)	C13B—C14B—C15B—C16B	0.0 (4)
C14A—C15A—C16A—C17A	0.4 (4)	C14B—C15B—C16B—C17B	0.2 (4)
C15A—C16A—C17A—C18A	−0.3 (5)	C15B—C16B—C17B—C18B	−0.2 (4)
C16A—C17A—C18A—C13A	0.2 (5)	C16B—C17B—C18B—C13B	0.0 (4)
O4A—C13A—C18A—C17A	179.3 (3)	O4B—C13B—C18B—C17B	−179.8 (2)
C14A—C13A—C18A—C17A	−0.3 (4)	C14B—C13B—C18B—C17B	0.2 (4)
O3A—C11A—N1A—C3A	176.5 (2)	O2B—C3B—N1B—C11B	0.3 (4)
C12A—C11A—N1A—C3A	−6.0 (4)	O1B—C3B—N1B—C11B	179.7 (2)
O3A—C11A—N1A—C1A	−9.3 (3)	O2B—C3B—N1B—C1B	−173.6 (3)
C12A—C11A—N1A—C1A	168.2 (2)	O1B—C3B—N1B—C1B	5.8 (3)
O2A—C3A—N1A—C11A	4.0 (4)	O3B—C11B—N1B—C3B	175.9 (2)
O1A—C3A—N1A—C11A	−176.5 (2)	C12B—C11B—N1B—C3B	−7.8 (4)
O2A—C3A—N1A—C1A	−170.8 (3)	O3B—C11B—N1B—C1B	−10.8 (3)
O1A—C3A—N1A—C1A	8.7 (3)	C12B—C11B—N1B—C1B	165.5 (2)
C4A—C1A—N1A—C11A	−80.3 (3)	C4B—C1B—N1B—C3B	101.5 (2)
C2A—C1A—N1A—C11A	159.3 (2)	C2B—C1B—N1B—C3B	−20.7 (2)
C4A—C1A—N1A—C3A	94.9 (2)	C4B—C1B—N1B—C11B	−72.9 (3)
C2A—C1A—N1A—C3A	−25.5 (2)	C2B—C1B—N1B—C11B	165.0 (2)
O2A—C3A—O1A—C2A	−166.6 (2)	O2B—C3B—O1B—C2B	−167.2 (2)
N1A—C3A—O1A—C2A	13.9 (3)	N1B—C3B—O1B—C2B	13.4 (3)
C5A—C2A—O1A—C3A	−155.78 (19)	C5B—C2B—O1B—C3B	−152.58 (19)
C1A—C2A—O1A—C3A	−29.7 (2)	C1B—C2B—O1B—C3B	−26.0 (2)
C14A—C13A—O4A—C12A	11.1 (4)	C14B—C13B—O4B—C12B	−4.8 (3)
C18A—C13A—O4A—C12A	−168.4 (2)	C18B—C13B—O4B—C12B	175.3 (2)
C11A—C12A—O4A—C13A	−80.0 (3)	C19B—C12B—O4B—C13B	169.2 (2)
C19A—C12A—O4A—C13A	162.8 (2)	C11B—C12B—O4B—C13B	−72.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1A—H1A···O3B	1.00	2.61	3.373 (3)	133
C1B—H1B···O3A	1.00	2.57	3.568 (3)	174
C18A—H18A···O4Bⁱ	0.95	2.52	3.445 (4)	165
C18B—H18B···O4Aⁱⁱ	0.95	2.69	3.564 (4)	154

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

Acknowledgements

We are grateful to the Royal Society and the University of London Central Research Fund for their financial support to JE, and the EPSRC National Mass Spectrometry Service (Swansea) for accurate mass determination.

References

Chavda, S., Eames, J., Flinn, A., Motevalli, M. & Malatesti, N. (2006a). Acta Cryst. E62, o4037–o4038. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chavda, S., Eames, J., Flinn, A., Motevalli, M. & Malatesti, N. (2006b). Acta Cryst. E62, o4039–o4041. Web of Science CSD CrossRef IUCr Journals Google Scholar
Coumbarides, G. S., Dingjan, M., Eames, J., Motevalli, M. & Malatesti, N. (2006). Acta Cryst. E62, o4035–o4036. Web of Science CSD CrossRef IUCr Journals Google Scholar
Coumbarides, G. S., Eames, J., Motevalli, M., Malatesti, N. & Yohannes, Y. (2006a). Acta Cryst. E62, o4032–o4034. Web of Science CSD CrossRef IUCr Journals Google Scholar
Coumbarides, G. S., Eames, J., Motevalli, M., Malatesti, N. & Yohannes, Y. (2006b). Acta Cryst. E62, o4041–o4042. Web of Science CSD CrossRef IUCr Journals Google Scholar
Enraf–Nonius (1994). CAD-4-PC Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar

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