(3R*,6R*,4′S*,8′R*,3′′R*,6′′R*)-3,3′′-Diisopropyl-6,6′′-dimethyl-2′,6′-di­phenyl­dispiro­[cyclo­hexane-1,4′-(3,7-dioxa-2,6-di­aza­bicyclo­[3.3.0]octa­ne)-8′,1′′-cyclo­hexa­ne]-2,2′′-dione

Ansari, A.; Majidi, L.; Fihi, R.; Daran, J.-C.; Azrour, M.

doi:10.1107/S1600536813017054

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 7| July 2013| Pages o1162-o1163

https://doi.org/10.1107/S1600536813017054

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(3R,6R,4′S,8′R,3′′R,6′′R)-3,3′′-Diisopropyl-6,6′′-dimethyl-2′,6′-diphenyldispiro[cyclohexane-1,4′-(3,7-dioxa-2,6-diazabicyclo[3.3.0]octane)-8′,1′′-cyclohexane]-2,2′′-dione

Abdeslam Ansari,^a Lhou Majidi,^a Rachid Fihi,^a Jean-Claude Daran ^b and Mohamed Azrour ^c ^*

^aLaboratoire des Substances Naturelles et Synthèse et Dynamique Moléculaire, Faculté des Sciences et Techniques, Errachidia, Morocco, ^bLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse cedex, France, and ^cLaboratoire de Chimie Physique des Matériaux, Faculté des Sciences et Techniques, BP 509, Errachidia, Morocco
^*Correspondence e-mail: med.azrour@gmail.com

(Received 26 April 2013; accepted 19 June 2013; online 26 June 2013)

The two oxazolidine rings (A and B) of the title compound, C₃₄H₄₄N₂O₄, display roughly half-chair conformations, which could be described as twisted on the C—O bond. Together, the fused oxazolidine rings have a butterfly shape, with the H atoms attached to the ring junction C atoms in a cis orientation. The cyclohexane rings of both p-menthone fragments display chair conformations. The absolute configuration could not be determined from the X-ray diffraction data, but the relative configuration of the stereocentres could be deduced.

Related literature

For a related synthesis, see: Brüning et al. (1973 ); Tanka et al. (1972 ). For the properties of p-menthane derivatives, see: Ito et al. (2009 ); Kharchouf et al. (2011 , 2012 ); Majidi et al. (2010 ); Clark (1990 ); Umemoko (1998 ); Boelens (1993 ); Wagner et al. (2004 ). For related structures, see: Iball et al. (1968 , 1986 ); Aurich et al. (1989 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₃₄H₄₄N₂O₄
M_r = 544.71
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.5037 (6) Å
b = 12.4162 (10) Å
c = 24.8982 (18) Å
V = 2938.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 180 K
0.37 × 0.13 × 0.06 mm

Data collection

Agilent Xcalibur diffractometer
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Agilent, 2010 ) T_min = 0.908, T_max = 1.000
24309 measured reflections
5963 independent reflections
3751 reflections with I > 2σ(I)
R_int = 0.098

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.080
S = 0.87
5963 reflections
367 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536813017054/fy2097sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813017054/fy2097Isup2.hkl

checkCIF report

Comment top

Synthesis of various p-menthane derivatives is studied extensively, with the goal to obtain biologically active and ecofriendly corrosion inhibitor compounds (Ito et al., 2009; Kharchouf et al., 2011; 2012; Majidi et al., 2010). p-Menthan-3-one, 1 (Menthone) have become the key starting natural compound for the synthesis of a number of substances exhibiting various kinds of biological activity (Ito et al., 2009). Menthone, a monoterpene ketone, occurs in nature and is widely present in high concentration in a few Mentha species, such as Mentha specata aromentha (Clark, 1990), M. Avrvensis (Umemoko, 1998) and the essential oils of pepperimint and other mint oils (Boelens, 1993). On the other hand, isoxazolidine rings are the frame of a number of natural products and antibiotics and are extensively used in the synthesis of a great many biologically important compounds (Wagner et al., 2004). The goal of the present study was to obtain a new p-menthane derivative having two isoxazolidine moieties. This latter is of interest, because it can exhibit biological activity and has useful properties as precursor for synthesis.

The structure of the title compound is built up from two fused five membered oxazolidine rings sharing two C atoms to which p-menthone and phenyl rings are attached (Fig. 1). As observed in other diisooxazolidines (Iball et al., 1968; 1986; Aurich et al., 1989), the two oxazolidine rings display roughly half-chair conformation with the puckering parameters Q(2)= 0.366 (2) Å and φ= 350.2 (3)° for ring A (C1, C2, C3, O1, N2) and Q(2)= 0.360 (2) Å and φ(2= 347.7 (3)° for ring B (C2, C3, C4, O2, N3) (Cremer & Pople, 1975). They could be regarded as twisted on C1—O1 and C4—O2, respectively. This two fused rings have a butterfly shape with the H atoms attached to the C2—C3 edge in cis position. Both p-menthone fragments display a chair conformation with the puckering amplitudes of θ= 180.0 (2)°, φ= 74 (10)° and θ= 1.2 (2)°, φ= 314 (8)° respectively. The packing is stabilized only by van der Waals interactions.

Related literature top

For a related synthesis, see: Brüning et al. (1973); Tanka et al. (1972). For the properties of p-menthane derivatives, see: Ito et al. (2009); Kharchouf et al. (2011, 2012); Majidi et al. (2010); Clark (1990); Umemoko (1998); Boelens (1993); Wagner et al. (2004). For related structures, see: Iball et al. (1968, 1986); Aurich et al. (1989). For ring conformations, see: Cremer & Pople (1975).

Experimental top

2-Hydroxymethyle menthone (1) and n-diphenylnitrone (2) were prepared according to literature procedures (Brüning et al., 1973; Tanka et al., 1972).

To a mixture of 6 mmoles of 2-hydroxymethylene menthone and 6 mmoles of n-diphenylnitrone in 20 ml of ethyl acetate (Fig. 2) was added a catalytic amount of K₁₀(montmorillonite/FeIII). The reaction mixture was stirred for 48 h at 25°C and then filtered. The solvent was removed and the product was purified by recrystallization in ethanol (yield 67%). Single cristals were obtained by slow evaporation of an ethanol solution at room temperature.

Structure description top

For a related synthesis, see: Brüning et al. (1973); Tanka et al. (1972). For the properties of p-menthane derivatives, see: Ito et al. (2009); Kharchouf et al. (2011, 2012); Majidi et al. (2010); Clark (1990); Umemoko (1998); Boelens (1993); Wagner et al. (2004). For related structures, see: Iball et al. (1968, 1986); Aurich et al. (1989). For ring conformations, see: Cremer & Pople (1975).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of the title compound with the atom labeling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Scheme showing the synthetic pathway

(3R*,6R*,4'S*,8'R*,3''R*,6''R*)-3,3''-Diisopropyl-6,6''-dimethyl-2',6'-diphenyldispiro[cyclohexane-1,4'-(3,7-dioxa-2,6-diazabicyclo[3.3.0]octane)-8',1''-cyclohexane]-2,2''-dione top

Crystal data top

C₃₄H₄₄N₂O₄	F(000) = 1176
M_r = 544.71	D_x = 1.231 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6434 reflections
a = 9.5037 (6) Å	θ = 3.0–28.6°
b = 12.4162 (10) Å	µ = 0.08 mm⁻¹
c = 24.8982 (18) Å	T = 180 K
V = 2938.0 (4) Å³	Parallepiped, colourless
Z = 4	0.37 × 0.13 × 0.06 mm

Data collection top

Agilent Xcalibur diffractometer	5963 independent reflections
Radiation source: fine-focus sealed tube	3751 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.098
Detector resolution: 8.2632 pixels mm^-1	θ_max = 26.4°, θ_min = 3.0°
ω scans	h = −11→10
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Agilent, 2010)	k = −15→15
T_min = 0.908, T_max = 1.000	l = −31→31
24309 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.0302P)²] where P = (F_o² + 2F_c²)/3
5963 reflections	(Δ/σ)_max = 0.001
367 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₃₄H₄₄N₂O₄	V = 2938.0 (4) Å³
M_r = 544.71	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.5037 (6) Å	µ = 0.08 mm⁻¹
b = 12.4162 (10) Å	T = 180 K
c = 24.8982 (18) Å	0.37 × 0.13 × 0.06 mm

Data collection top

Agilent Xcalibur diffractometer	5963 independent reflections
Absorption correction: multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Agilent, 2010)	3751 reflections with I > 2σ(I)
T_min = 0.908, T_max = 1.000	R_int = 0.098
24309 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 0.87	Δρ_max = 0.17 e Å⁻³
5963 reflections	Δρ_min = −0.19 e Å⁻³
367 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
C1	0.19364 (19)	0.00584 (18)	0.11958 (8)	0.0199 (5)
C2	0.3120 (2)	0.07456 (17)	0.14271 (9)	0.0221 (5)
H2	0.3371	0.0516	0.1800	0.026*
C3	0.4346 (2)	0.05539 (17)	0.10324 (8)	0.0218 (5)
H3	0.5146	0.0178	0.1214	0.026*
C4	0.47632 (19)	0.16842 (17)	0.08623 (9)	0.0225 (5)
C11	0.1960 (2)	−0.10828 (18)	0.14225 (9)	0.0238 (5)
C12	0.09059 (19)	−0.18512 (17)	0.11807 (9)	0.0241 (5)
H12	0.1106	−0.1858	0.0786	0.029*
C13	−0.0568 (2)	−0.13708 (18)	0.12394 (9)	0.0300 (6)
H13A	−0.1258	−0.1838	0.1054	0.036*
H13B	−0.0826	−0.1342	0.1624	0.036*
C14	−0.0626 (2)	−0.02464 (18)	0.10027 (10)	0.0306 (6)
H14A	−0.1582	0.0053	0.1056	0.037*
H14B	−0.0450	−0.0289	0.0611	0.037*
C15	0.04500 (19)	0.05139 (17)	0.12565 (9)	0.0233 (5)
H15	0.0404	0.1223	0.1067	0.028*
C21	0.4178 (2)	−0.12024 (18)	0.05577 (8)	0.0240 (5)
C22	0.3369 (2)	−0.18798 (19)	0.02411 (9)	0.0295 (6)
H22	0.2577	−0.1598	0.0056	0.035*
C23	0.3692 (2)	−0.2946 (2)	0.01916 (9)	0.0358 (6)
H23	0.3107	−0.3401	−0.0019	0.043*
C24	0.4860 (2)	−0.3371 (2)	0.04434 (10)	0.0397 (7)
H24	0.5074	−0.4116	0.0416	0.048*
C25	0.5706 (2)	−0.2691 (2)	0.07344 (10)	0.0385 (6)
H25	0.6530	−0.2968	0.0900	0.046*
C26	0.5387 (2)	−0.1620 (2)	0.07909 (9)	0.0320 (6)
H26	0.5994	−0.1163	0.0990	0.038*
C31	0.3156 (2)	0.25848 (19)	0.18430 (10)	0.0290 (6)
C32	0.3771 (3)	0.2242 (2)	0.23146 (10)	0.0455 (7)
H32	0.4013	0.1505	0.2361	0.055*
C33	0.4036 (3)	0.2983 (3)	0.27216 (12)	0.0649 (9)
H33	0.4469	0.2749	0.3045	0.078*
C34	0.3683 (3)	0.4037 (3)	0.26628 (13)	0.0607 (9)
H34	0.3854	0.4533	0.2946	0.073*
C35	0.3081 (3)	0.4380 (2)	0.21937 (13)	0.0576 (8)
H35	0.2859	0.5121	0.2147	0.069*
C36	0.2796 (2)	0.3658 (2)	0.17905 (11)	0.0477 (7)
H36	0.2346	0.3898	0.1472	0.057*
C41	0.5902 (2)	0.21326 (18)	0.12434 (9)	0.0244 (5)
C42	0.6212 (2)	0.33086 (18)	0.11805 (9)	0.0318 (6)
H42	0.5296	0.3696	0.1222	0.038*
C43	0.6684 (2)	0.3473 (2)	0.05962 (10)	0.0437 (7)
H43A	0.6837	0.4251	0.0530	0.052*
H43B	0.7589	0.3097	0.0538	0.052*
C44	0.5597 (2)	0.3048 (2)	0.01977 (10)	0.0423 (7)
H44A	0.4722	0.3474	0.0233	0.051*
H44B	0.5958	0.3148	−0.0172	0.051*
C45	0.5259 (2)	0.18599 (19)	0.02852 (8)	0.0316 (6)
H45	0.4465	0.1665	0.0040	0.038*
C121	0.1084 (2)	−0.30106 (18)	0.13674 (9)	0.0323 (6)
H121	0.2116	−0.3163	0.1382	0.039*
C122	0.0492 (3)	−0.3200 (2)	0.19291 (10)	0.0504 (7)
H12A	−0.0523	−0.3058	0.1928	0.076*
H12B	0.0955	−0.2714	0.2184	0.076*
H12C	0.0662	−0.3948	0.2036	0.076*
C123	0.0439 (2)	−0.37914 (19)	0.09676 (11)	0.0463 (7)
H12D	−0.0577	−0.3665	0.0945	0.069*
H12E	0.0612	−0.4532	0.1086	0.069*
H12F	0.0865	−0.3681	0.0614	0.069*
C151	0.0135 (2)	0.06976 (19)	0.18542 (9)	0.0314 (6)
H15A	0.0318	0.0033	0.2054	0.047*
H15B	−0.0855	0.0903	0.1898	0.047*
H15C	0.0739	0.1275	0.1992	0.047*
C421	0.7198 (2)	0.37487 (19)	0.16169 (11)	0.0410 (7)
H421	0.6917	0.3406	0.1964	0.049*
C422	0.7019 (3)	0.4951 (2)	0.16820 (14)	0.0645 (9)
H42A	0.7648	0.5211	0.1966	0.097*
H42B	0.6042	0.5111	0.1779	0.097*
H42C	0.7252	0.5312	0.1343	0.097*
C423	0.8732 (2)	0.3466 (2)	0.15191 (12)	0.0554 (8)
H42D	0.9069	0.3843	0.1198	0.083*
H42E	0.8822	0.2687	0.1466	0.083*
H42F	0.9296	0.3685	0.1830	0.083*
C451	0.6509 (2)	0.1136 (2)	0.01454 (9)	0.0402 (7)
H45A	0.7289	0.1286	0.0392	0.060*
H45B	0.6809	0.1278	−0.0224	0.060*
H45C	0.6230	0.0379	0.0180	0.060*
N2	0.37834 (15)	−0.00963 (14)	0.05922 (7)	0.0228 (4)
N3	0.27983 (16)	0.18972 (14)	0.14028 (7)	0.0263 (4)
O1	0.22708 (13)	0.00147 (12)	0.06227 (5)	0.0229 (3)
O2	0.34705 (13)	0.22877 (12)	0.09175 (6)	0.0267 (4)
O11	0.27485 (15)	−0.13285 (13)	0.17847 (6)	0.0369 (4)
O41	0.65421 (14)	0.15395 (13)	0.15382 (6)	0.0333 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0225 (11)	0.0246 (12)	0.0126 (11)	−0.0020 (9)	−0.0001 (9)	0.0004 (11)
C2	0.0219 (11)	0.0222 (13)	0.0221 (13)	−0.0006 (9)	−0.0012 (9)	−0.0006 (11)
C3	0.0216 (11)	0.0240 (13)	0.0199 (12)	−0.0030 (9)	−0.0015 (10)	−0.0009 (11)
C4	0.0190 (10)	0.0247 (13)	0.0239 (12)	0.0007 (9)	−0.0005 (9)	0.0036 (10)
C11	0.0192 (11)	0.0326 (14)	0.0198 (12)	0.0032 (10)	0.0036 (10)	0.0019 (11)
C12	0.0254 (11)	0.0250 (13)	0.0219 (13)	−0.0010 (10)	−0.0023 (9)	0.0036 (11)
C13	0.0251 (12)	0.0310 (15)	0.0340 (14)	−0.0036 (10)	−0.0006 (10)	−0.0012 (12)
C14	0.0241 (12)	0.0359 (16)	0.0320 (14)	0.0019 (11)	−0.0035 (10)	−0.0015 (12)
C15	0.0248 (12)	0.0252 (13)	0.0200 (12)	0.0021 (10)	0.0004 (10)	0.0009 (11)
C21	0.0238 (11)	0.0293 (14)	0.0189 (12)	0.0003 (10)	0.0059 (10)	−0.0024 (12)
C22	0.0270 (12)	0.0358 (15)	0.0256 (14)	0.0010 (11)	0.0032 (10)	−0.0089 (12)
C23	0.0333 (13)	0.0376 (17)	0.0366 (15)	−0.0031 (12)	0.0067 (11)	−0.0171 (13)
C24	0.0388 (14)	0.0302 (15)	0.0500 (17)	0.0016 (12)	0.0097 (12)	−0.0135 (14)
C25	0.0353 (14)	0.0361 (16)	0.0440 (17)	0.0091 (12)	0.0002 (12)	−0.0051 (14)
C26	0.0286 (12)	0.0328 (15)	0.0347 (15)	0.0021 (11)	−0.0005 (11)	−0.0090 (12)
C31	0.0205 (12)	0.0317 (15)	0.0348 (15)	−0.0031 (10)	0.0007 (10)	−0.0104 (13)
C32	0.0694 (18)	0.0360 (17)	0.0312 (15)	−0.0123 (14)	−0.0038 (14)	−0.0065 (14)
C33	0.094 (2)	0.063 (2)	0.0376 (18)	−0.0190 (18)	−0.0093 (16)	−0.0116 (18)
C34	0.068 (2)	0.056 (2)	0.059 (2)	−0.0174 (17)	0.0087 (17)	−0.0305 (19)
C35	0.0512 (17)	0.0399 (18)	0.082 (2)	0.0032 (14)	−0.0046 (17)	−0.0272 (18)
C36	0.0443 (15)	0.0363 (17)	0.063 (2)	0.0086 (13)	−0.0112 (13)	−0.0184 (16)
C41	0.0216 (12)	0.0271 (14)	0.0244 (13)	0.0013 (10)	0.0041 (10)	0.0039 (12)
C42	0.0248 (12)	0.0269 (14)	0.0437 (16)	0.0005 (10)	0.0001 (11)	0.0061 (12)
C43	0.0361 (13)	0.0358 (15)	0.0592 (18)	−0.0059 (12)	0.0021 (13)	0.0159 (15)
C44	0.0451 (14)	0.0447 (18)	0.0372 (16)	−0.0022 (13)	0.0030 (12)	0.0203 (14)
C45	0.0308 (12)	0.0414 (16)	0.0225 (13)	−0.0021 (11)	−0.0001 (10)	0.0096 (12)
C121	0.0379 (13)	0.0263 (14)	0.0327 (14)	−0.0034 (10)	0.0001 (11)	0.0063 (12)
C122	0.0646 (17)	0.0433 (17)	0.0431 (17)	−0.0046 (14)	0.0067 (13)	0.0184 (14)
C123	0.0570 (16)	0.0292 (16)	0.0526 (18)	−0.0078 (13)	0.0031 (13)	−0.0004 (15)
C151	0.0320 (13)	0.0353 (15)	0.0269 (14)	0.0010 (11)	0.0049 (11)	−0.0020 (12)
C421	0.0323 (14)	0.0270 (14)	0.0637 (18)	−0.0071 (11)	−0.0068 (12)	−0.0021 (14)
C422	0.0462 (17)	0.0366 (17)	0.111 (3)	−0.0039 (14)	−0.0063 (17)	−0.015 (2)
C423	0.0355 (15)	0.0376 (16)	0.093 (2)	−0.0077 (13)	−0.0169 (14)	0.0026 (17)
C451	0.0358 (13)	0.0536 (18)	0.0313 (15)	0.0012 (12)	0.0106 (11)	0.0028 (14)
N2	0.0167 (9)	0.0292 (11)	0.0227 (10)	−0.0012 (8)	0.0007 (8)	−0.0035 (10)
N3	0.0275 (10)	0.0274 (11)	0.0240 (11)	−0.0036 (8)	0.0034 (8)	−0.0001 (10)
O1	0.0197 (8)	0.0323 (9)	0.0166 (8)	0.0005 (7)	−0.0002 (6)	0.0007 (8)
O2	0.0239 (8)	0.0286 (9)	0.0276 (9)	0.0028 (7)	0.0002 (7)	0.0057 (8)
O11	0.0371 (9)	0.0362 (10)	0.0372 (10)	−0.0018 (8)	−0.0120 (8)	0.0095 (9)
O41	0.0339 (9)	0.0284 (9)	0.0375 (10)	−0.0036 (7)	−0.0097 (7)	0.0073 (8)

Geometric parameters (Å, º) top

C1—O1	1.463 (2)	C34—C35	1.369 (4)
C1—C2	1.525 (3)	C34—H34	0.9500
C1—C11	1.525 (3)	C35—C36	1.373 (3)
C1—C15	1.529 (3)	C35—H35	0.9500
C2—N3	1.463 (3)	C36—H36	0.9500
C2—C3	1.543 (3)	C41—O41	1.204 (2)
C2—H2	1.0000	C41—C42	1.498 (3)
C3—N2	1.463 (3)	C42—C421	1.536 (3)
C3—C4	1.519 (3)	C42—C43	1.536 (3)
C3—H3	1.0000	C42—H42	1.0000
C4—O2	1.446 (2)	C43—C44	1.526 (3)
C4—C45	1.528 (3)	C43—H43A	0.9900
C4—C41	1.543 (3)	C43—H43B	0.9900
C11—O11	1.212 (2)	C44—C45	1.525 (3)
C11—C12	1.509 (3)	C44—H44A	0.9900
C12—C121	1.522 (3)	C44—H44B	0.9900
C12—C13	1.530 (3)	C45—C451	1.530 (3)
C12—H12	1.0000	C45—H45	1.0000
C13—C14	1.516 (3)	C121—C123	1.519 (3)
C13—H13A	0.9900	C121—C122	1.526 (3)
C13—H13B	0.9900	C121—H121	1.0000
C14—C15	1.529 (3)	C122—H12A	0.9800
C14—H14A	0.9900	C122—H12B	0.9800
C14—H14B	0.9900	C122—H12C	0.9800
C15—C151	1.535 (3)	C123—H12D	0.9800
C15—H15	1.0000	C123—H12E	0.9800
C21—C22	1.386 (3)	C123—H12F	0.9800
C21—C26	1.388 (3)	C151—H15A	0.9800
C21—N2	1.426 (3)	C151—H15B	0.9800
C22—C23	1.365 (3)	C151—H15C	0.9800
C22—H22	0.9500	C421—C422	1.512 (3)
C23—C24	1.380 (3)	C421—C423	1.519 (3)
C23—H23	0.9500	C421—H421	1.0000
C24—C25	1.372 (3)	C422—H42A	0.9800
C24—H24	0.9500	C422—H42B	0.9800
C25—C26	1.370 (3)	C422—H42C	0.9800
C25—H25	0.9500	C423—H42D	0.9800
C26—H26	0.9500	C423—H42E	0.9800
C31—C32	1.379 (3)	C423—H42F	0.9800
C31—C36	1.382 (3)	C451—H45A	0.9800
C31—N3	1.430 (3)	C451—H45B	0.9800
C32—C33	1.392 (4)	C451—H45C	0.9800
C32—H32	0.9500	N2—O1	1.4461 (19)
C33—C34	1.358 (4)	N3—O2	1.450 (2)
C33—H33	0.9500

O1—C1—C2	103.24 (15)	C35—C36—H36	119.6
O1—C1—C11	108.86 (17)	C31—C36—H36	119.6
C2—C1—C11	111.67 (16)	O41—C41—C42	124.1 (2)
O1—C1—C15	108.11 (15)	O41—C41—C4	120.54 (19)
C2—C1—C15	115.93 (18)	C42—C41—C4	115.16 (19)
C11—C1—C15	108.68 (16)	C41—C42—C421	113.1 (2)
N3—C2—C1	112.15 (17)	C41—C42—C43	106.6 (2)
N3—C2—C3	106.39 (16)	C421—C42—C43	116.40 (18)
C1—C2—C3	103.31 (16)	C41—C42—H42	106.7
N3—C2—H2	111.5	C421—C42—H42	106.7
C1—C2—H2	111.5	C43—C42—H42	106.7
C3—C2—H2	111.5	C44—C43—C42	111.85 (18)
N2—C3—C4	113.36 (17)	C44—C43—H43A	109.2
N2—C3—C2	106.65 (15)	C42—C43—H43A	109.2
C4—C3—C2	103.44 (16)	C44—C43—H43B	109.2
N2—C3—H3	111.0	C42—C43—H43B	109.2
C4—C3—H3	111.0	H43A—C43—H43B	107.9
C2—C3—H3	111.0	C45—C44—C43	112.6 (2)
O2—C4—C3	103.33 (15)	C45—C44—H44A	109.1
O2—C4—C45	106.12 (16)	C43—C44—H44A	109.1
C3—C4—C45	118.35 (18)	C45—C44—H44B	109.1
O2—C4—C41	110.52 (16)	C43—C44—H44B	109.1
C3—C4—C41	110.18 (17)	H44A—C44—H44B	107.8
C45—C4—C41	108.08 (16)	C44—C45—C4	109.72 (19)
O11—C11—C12	123.3 (2)	C44—C45—C451	111.84 (18)
O11—C11—C1	121.21 (19)	C4—C45—C451	111.68 (18)
C12—C11—C1	115.48 (18)	C44—C45—H45	107.8
C11—C12—C121	113.74 (17)	C4—C45—H45	107.8
C11—C12—C13	108.86 (18)	C451—C45—H45	107.8
C121—C12—C13	116.18 (17)	C123—C121—C12	111.02 (18)
C11—C12—H12	105.7	C123—C121—C122	110.7 (2)
C121—C12—H12	105.7	C12—C121—C122	112.6 (2)
C13—C12—H12	105.7	C123—C121—H121	107.4
C14—C13—C12	110.80 (17)	C12—C121—H121	107.4
C14—C13—H13A	109.5	C122—C121—H121	107.4
C12—C13—H13A	109.5	C121—C122—H12A	109.5
C14—C13—H13B	109.5	C121—C122—H12B	109.5
C12—C13—H13B	109.5	H12A—C122—H12B	109.5
H13A—C13—H13B	108.1	C121—C122—H12C	109.5
C13—C14—C15	112.55 (18)	H12A—C122—H12C	109.5
C13—C14—H14A	109.1	H12B—C122—H12C	109.5
C15—C14—H14A	109.1	C121—C123—H12D	109.5
C13—C14—H14B	109.1	C121—C123—H12E	109.5
C15—C14—H14B	109.1	H12D—C123—H12E	109.5
H14A—C14—H14B	107.8	C121—C123—H12F	109.5
C14—C15—C1	110.42 (17)	H12D—C123—H12F	109.5
C14—C15—C151	111.22 (17)	H12E—C123—H12F	109.5
C1—C15—C151	109.34 (17)	C15—C151—H15A	109.5
C14—C15—H15	108.6	C15—C151—H15B	109.5
C1—C15—H15	108.6	H15A—C151—H15B	109.5
C151—C15—H15	108.6	C15—C151—H15C	109.5
C22—C21—C26	118.0 (2)	H15A—C151—H15C	109.5
C22—C21—N2	118.23 (19)	H15B—C151—H15C	109.5
C26—C21—N2	123.5 (2)	C422—C421—C423	110.71 (19)
C23—C22—C21	121.0 (2)	C422—C421—C42	111.0 (2)
C23—C22—H22	119.5	C423—C421—C42	113.0 (2)
C21—C22—H22	119.5	C422—C421—H421	107.3
C22—C23—C24	120.7 (2)	C423—C421—H421	107.3
C22—C23—H23	119.6	C42—C421—H421	107.3
C24—C23—H23	119.6	C421—C422—H42A	109.5
C25—C24—C23	118.4 (2)	C421—C422—H42B	109.5
C25—C24—H24	120.8	H42A—C422—H42B	109.5
C23—C24—H24	120.8	C421—C422—H42C	109.5
C26—C25—C24	121.4 (2)	H42A—C422—H42C	109.5
C26—C25—H25	119.3	H42B—C422—H42C	109.5
C24—C25—H25	119.3	C421—C423—H42D	109.5
C25—C26—C21	120.2 (2)	C421—C423—H42E	109.5
C25—C26—H26	119.9	H42D—C423—H42E	109.5
C21—C26—H26	119.9	C421—C423—H42F	109.5
C32—C31—C36	118.9 (2)	H42D—C423—H42F	109.5
C32—C31—N3	124.7 (2)	H42E—C423—H42F	109.5
C36—C31—N3	116.4 (2)	C45—C451—H45A	109.5
C31—C32—C33	119.5 (3)	C45—C451—H45B	109.5
C31—C32—H32	120.3	H45A—C451—H45B	109.5
C33—C32—H32	120.3	C45—C451—H45C	109.5
C34—C33—C32	120.9 (3)	H45A—C451—H45C	109.5
C34—C33—H33	119.5	H45B—C451—H45C	109.5
C32—C33—H33	119.5	C21—N2—O1	110.86 (14)
C33—C34—C35	119.7 (3)	C21—N2—C3	118.73 (17)
C33—C34—H34	120.2	O1—N2—C3	105.74 (14)
C35—C34—H34	120.2	C31—N3—O2	109.51 (15)
C34—C35—C36	120.2 (3)	C31—N3—C2	120.11 (18)
C34—C35—H35	119.9	O2—N3—C2	105.61 (15)
C36—C35—H35	119.9	N2—O1—C1	105.71 (13)
C35—C36—C31	120.8 (3)	C4—O2—N3	106.28 (14)

Experimental details

Crystal data
Chemical formula	C₃₄H₄₄N₂O₄
M_r	544.71
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	180
a, b, c (Å)	9.5037 (6), 12.4162 (10), 24.8982 (18)
V (Å³)	2938.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.37 × 0.13 × 0.06

Data collection
Diffractometer	Agilent Xcalibur
Absorption correction	Multi-scan (SCALE3 ABSPACK in CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.908, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	24309, 5963, 3751
R_int	0.098
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.080, 0.87
No. of reflections	5963
No. of parameters	367
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CrysAlis PRO (Agilent, 2010), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012).

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