Moscham­indole

Cox, P.J.; Fergusson, M.; Nahar, L.; Sarker, S.D.

doi:10.1107/S1600536800020730

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Moschamindole

P. J. Cox, M. Fergusson, L. Nahar and S. D. Sarker

The solid state structure of moschamindole {systematic name: 10-[2-(4-hydroxy-3-methoxyphenyl)]-1,2,3,4,10,10a-hexahydro-6H-furo[2,3,4-jk]pyrrolo[4,3,2-ef]-3-benzazocin-1-one}, C₂₀H₁₈N₂O₄ is similar to its solution state structure, previously determined by NMR, and evidence of intermolecular hydrogen bonding is now presented.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020730/cf6033sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020730/cf6033Isup2.hkl Contains datablock I

CCDC reference: 155899

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.005 Å
R factor = 0.046
wR factor = 0.097
Data-to-parameter ratio = 7.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSMU_01  Alert C The ratio of given/expected absorption coefficient lies
          outside the range 0.99 <> 1.01
          Calculated value of mu =     0.105
          Value of mu given      =     0.110

PLAT_352  Alert C Short N-H Bond (0.87A)     N(2)   -   H(2)   =       0.76 Ang.

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.50
         From the CIF: _reflns_number_total               1839
         Count of symmetry unique reflns         1859
         Completeness (_total/calc)             98.92%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured         0
         Fraction of Friedel pairs measured     0.000
         Are heavy atom types Z>Si present           no
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

Comment top

Moschamindole, (I), was obtained as one of four indole alkaloids from Centaurea moschata and its molecular structure was determined by extensive one-dimensional and two-dimensional NMR spectroscopy (Sarker et al., 1997). We undertook an X-ray study to confirm the structure determined from NMR data and to establish the presence of hydrogen bonding.

Each H atom (H1 and H2) at the donor N-atom positions (N1 and N2) is involved in an intermolecular hydrogen bond (with O4 and O2, respectively). There is also a weak C11—H11···O4 intermolecular hydrogen bond. Three short intramolecular distances are present where the H···A distance `closes' a five-membered ring. Details of these geometries are shown in Table 2. The absolute stereochemistry of the molecule has not been determined but the two chiral centres, C1 and C2, have the same designation (shown as R in Fig. 1). Here, the torsion angle H1—C1—C2—H2 is -115 (1)°. The eight-membered ring has a conformation where atoms C2, C4, C5, C6, C7 and C8 lie within 0.05 Å of a mean plane, with atoms N1 and C3 displaced to the same side of this plane by 1.15 (4) and 1.28 (4) Å, respectively. The other four rings adopt planar conformations and the dihedral angle between the aryl ring and the dihydrofuran ring is 43.3 (1)°. As a result of ring fusion, valency angle distortions are present around C6, C7 and C8 (Table 1).

Experimental top

Moschamindole was obtained from the methanol extract of the seeds of Centaurea moschata. Crystals for X-ray work were obtained from a methanol solution.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. The atomic arrangement in the title molecule. Displacement ellipsoids are shown at the 50% probability level.

{2-(3-methoxy-4-hydroxyphenyl)}-dihydrofuro[kl]-1H- pyrrolo[fg]-2-oxo-1,2,3,4,5,6-hexahydro-3-benzazocine top

Crystal data top

C₂₀H₁₈N₂O₄	F(000) = 368
M_r = 350.36	D_x = 1.493 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 4.8724 (3) Å	Cell parameters from 3310 reflections
b = 15.2803 (9) Å	θ = 2.9–27.5°
c = 10.6940 (7) Å	µ = 0.11 mm⁻¹
β = 101.840 (3)°	T = 150 K
V = 779.25 (8) Å³	Plate, yellow
Z = 2	0.4 × 0.2 × 0.05 mm

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1272 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR591 rotating anode	R_int = 0.080
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
Detector resolution: 9.091 pixels mm^-1	h = −6→6
ϕ and ω scans to fill Ewald sphere	k = −19→18
5565 measured reflections	l = −12→13
1839 independent 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0348P)²] where P = (F_o² + 2F_c²)/3
1839 reflections	(Δ/σ)_max = 0.007
245 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₄	V = 779.25 (8) Å³
M_r = 350.36	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 4.8724 (3) Å	µ = 0.11 mm⁻¹
b = 15.2803 (9) Å	T = 150 K
c = 10.6940 (7) Å	0.4 × 0.2 × 0.05 mm
β = 101.840 (3)°

Data collection top

Enraf Nonius KappaCCD area-detector diffractometer	1272 reflections with I > 2σ(I)
5565 measured reflections	R_int = 0.080
1839 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	1 restraint
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.22 e Å⁻³
1839 reflections	Δρ_min = −0.28 e Å⁻³
245 parameters

Special details top

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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
O1	1.0233 (5)	0.56379 (17)	0.8951 (2)	0.0272 (6)
O2	0.8375 (5)	0.37968 (15)	0.6439 (2)	0.0277 (6)
O3	0.2063 (5)	0.29402 (17)	1.0335 (2)	0.0302 (6)
O4	0.3312 (5)	0.37320 (18)	1.2564 (2)	0.0287 (6)
H4	0.188 (8)	0.326 (3)	1.229 (3)	0.034*
N1	0.4571 (6)	0.4431 (2)	0.5244 (3)	0.0253 (7)
H1	0.452 (8)	0.409 (3)	0.469 (4)	0.030*
N2	0.8203 (7)	0.7503 (2)	0.4526 (3)	0.0301 (8)
H2	0.922 (8)	0.784 (3)	0.435 (3)	0.036*
C1	0.8558 (7)	0.4855 (2)	0.8585 (3)	0.0210 (8)
H1A	0.9837	0.4376	0.8422	0.025*
C2	0.6525 (7)	0.5072 (2)	0.7311 (3)	0.0202 (8)
H2A	0.4580	0.5169	0.7451	0.024*
C3	0.6552 (7)	0.4363 (2)	0.6300 (3)	0.0198 (7)
C4	0.2289 (7)	0.5057 (3)	0.4966 (3)	0.0249 (8)
H4A	0.2013	0.5319	0.5778	0.030*
H4B	0.0544	0.4744	0.4578	0.030*
C5	0.2770 (7)	0.5787 (2)	0.4074 (3)	0.0262 (9)
H5A	0.3016	0.5521	0.3259	0.031*
H5B	0.1063	0.6155	0.3883	0.031*
C6	0.5239 (7)	0.6368 (2)	0.4562 (3)	0.0242 (8)
C7	0.7173 (7)	0.6401 (2)	0.5761 (3)	0.0229 (8)
C8	0.7749 (7)	0.5910 (2)	0.6915 (3)	0.0183 (7)
C9	0.9907 (7)	0.6167 (2)	0.7875 (3)	0.0244 (8)
C10	1.1662 (7)	0.6868 (3)	0.7815 (3)	0.0284 (9)
H10	1.3128	0.7014	0.8517	0.034*
C11	1.1207 (7)	0.7352 (2)	0.6697 (4)	0.0288 (9)
H11	1.2379	0.7835	0.6605	0.035*
C12	0.9010 (7)	0.7118 (2)	0.5717 (3)	0.0249 (8)
C13	0.5985 (8)	0.7047 (3)	0.3855 (3)	0.0297 (9)
H13	0.5065	0.7181	0.3005	0.036*
C14	0.7172 (7)	0.4572 (2)	0.9658 (3)	0.0211 (8)
C15	0.7808 (7)	0.4961 (2)	1.0836 (3)	0.0254 (8)
H15	0.9135	0.5424	1.0987	0.031*
C16	0.6509 (7)	0.4678 (3)	1.1822 (3)	0.0265 (8)
H16	0.6957	0.4948	1.2639	0.032*
C17	0.4596 (7)	0.4013 (2)	1.1600 (3)	0.0235 (8)
C18	0.3967 (7)	0.3605 (2)	1.0414 (3)	0.0224 (8)
C19	0.5267 (7)	0.3883 (2)	0.9439 (3)	0.0243 (8)
H19	0.4855	0.3603	0.8628	0.029*
C20	0.1393 (9)	0.2442 (3)	0.9195 (3)	0.0347 (9)
H20A	0.0760	0.2834	0.8468	0.042*
H20B	−0.0104	0.2026	0.9258	0.042*
H20C	0.3059	0.2121	0.9072	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0309 (14)	0.0320 (15)	0.0196 (13)	−0.0107 (12)	0.0070 (11)	−0.0003 (12)
O2	0.0350 (14)	0.0220 (14)	0.0271 (13)	0.0068 (13)	0.0092 (11)	−0.0017 (11)
O3	0.0382 (15)	0.0291 (14)	0.0253 (13)	−0.0074 (13)	0.0114 (12)	−0.0014 (12)
O4	0.0320 (13)	0.0376 (16)	0.0189 (12)	−0.0027 (13)	0.0110 (11)	0.0005 (12)
N1	0.0330 (17)	0.0222 (17)	0.0220 (18)	−0.0033 (15)	0.0091 (15)	−0.0054 (14)
N2	0.036 (2)	0.0203 (17)	0.0371 (19)	−0.0026 (16)	0.0153 (16)	0.0080 (15)
C1	0.0222 (17)	0.0227 (19)	0.0179 (18)	−0.0015 (16)	0.0035 (15)	−0.0005 (14)
C2	0.0222 (17)	0.0197 (18)	0.0202 (18)	−0.0012 (16)	0.0076 (15)	−0.0019 (15)
C3	0.0221 (17)	0.0181 (18)	0.0209 (18)	−0.0039 (17)	0.0084 (16)	0.0005 (15)
C4	0.0222 (18)	0.030 (2)	0.023 (2)	−0.0012 (17)	0.0050 (15)	0.0009 (16)
C5	0.0280 (19)	0.032 (2)	0.0197 (18)	0.0056 (18)	0.0070 (16)	0.0012 (16)
C6	0.027 (2)	0.023 (2)	0.026 (2)	0.0059 (17)	0.0121 (16)	0.0009 (16)
C7	0.0262 (19)	0.018 (2)	0.028 (2)	0.0027 (16)	0.0127 (16)	−0.0028 (16)
C8	0.0214 (16)	0.0162 (17)	0.0196 (17)	0.0018 (15)	0.0098 (15)	−0.0007 (14)
C9	0.0263 (19)	0.028 (2)	0.0217 (18)	−0.0019 (17)	0.0126 (16)	−0.0013 (16)
C10	0.0293 (19)	0.031 (2)	0.027 (2)	−0.0085 (19)	0.0107 (16)	−0.0137 (18)
C11	0.031 (2)	0.023 (2)	0.039 (2)	−0.0093 (18)	0.0210 (18)	−0.0054 (18)
C12	0.031 (2)	0.017 (2)	0.029 (2)	0.0013 (17)	0.0124 (17)	0.0009 (16)
C13	0.036 (2)	0.029 (2)	0.0264 (19)	0.0074 (19)	0.0123 (17)	0.0090 (18)
C14	0.0222 (17)	0.0252 (19)	0.0161 (17)	0.0035 (16)	0.0048 (14)	0.0002 (15)
C15	0.0261 (19)	0.025 (2)	0.026 (2)	0.0004 (17)	0.0072 (16)	0.0007 (16)
C16	0.0280 (18)	0.031 (2)	0.0200 (18)	0.0011 (17)	0.0043 (15)	−0.0030 (16)
C17	0.0254 (17)	0.030 (2)	0.0157 (18)	0.0050 (18)	0.0063 (15)	0.0055 (16)
C18	0.0227 (18)	0.0218 (18)	0.0227 (18)	0.0018 (16)	0.0051 (15)	0.0028 (16)
C19	0.0268 (18)	0.029 (2)	0.0177 (17)	0.0018 (18)	0.0066 (14)	−0.0003 (16)
C20	0.050 (2)	0.025 (2)	0.029 (2)	−0.007 (2)	0.0082 (19)	−0.0022 (18)

Geometric parameters (Å, º) top

O1—C9	1.389 (4)	C5—C6	1.500 (5)
O1—C1	1.456 (4)	C6—C13	1.376 (5)
O2—C3	1.227 (4)	C6—C7	1.428 (5)
O3—C18	1.366 (4)	C7—C12	1.422 (5)
O3—C20	1.417 (4)	C7—C8	1.422 (5)
O4—C17	1.380 (4)	C8—C9	1.367 (4)
N1—C3	1.331 (4)	C9—C10	1.380 (5)
N1—C4	1.451 (5)	C10—C11	1.384 (5)
N2—C13	1.360 (5)	C11—C12	1.383 (5)
N2—C12	1.384 (4)	C14—C15	1.370 (5)
C1—C14	1.509 (5)	C14—C19	1.391 (5)
C1—C2	1.546 (4)	C15—C16	1.404 (5)
C2—C8	1.510 (5)	C16—C17	1.367 (5)
C2—C3	1.532 (5)	C17—C18	1.389 (5)
C4—C5	1.516 (5)	C18—C19	1.393 (4)

C9—O1—C1	107.0 (2)	C7—C8—C2	132.2 (3)
C18—O3—C20	119.1 (3)	C8—C9—C10	125.2 (3)
C3—N1—C4	128.1 (3)	C8—C9—O1	113.2 (3)
C13—N2—C12	108.2 (3)	C10—C9—O1	121.6 (3)
O1—C1—C14	110.2 (3)	C9—C10—C11	117.6 (3)
O1—C1—C2	106.5 (3)	C12—C11—C10	118.6 (3)
C14—C1—C2	115.2 (3)	C11—C12—N2	128.1 (3)
C8—C2—C3	109.9 (2)	C11—C12—C7	124.6 (3)
C8—C2—C1	102.1 (3)	N2—C12—C7	107.2 (3)
C3—C2—C1	111.9 (3)	N2—C13—C6	111.5 (3)
O2—C3—N1	122.6 (3)	C15—C14—C19	120.0 (3)
O2—C3—C2	121.6 (3)	C15—C14—C1	121.5 (3)
N1—C3—C2	115.8 (3)	C19—C14—C1	118.5 (3)
N1—C4—C5	113.8 (3)	C14—C15—C16	120.4 (3)
C6—C5—C4	115.6 (3)	C17—C16—C15	119.6 (3)
C13—C6—C7	105.5 (3)	C16—C17—O4	119.9 (3)
C13—C6—C5	122.6 (3)	C16—C17—C18	120.5 (3)
C7—C6—C5	131.9 (3)	O4—C17—C18	119.6 (3)
C12—C7—C8	114.9 (3)	O3—C18—C17	114.2 (3)
C12—C7—C6	107.5 (3)	O3—C18—C19	125.9 (3)
C8—C7—C6	137.5 (3)	C17—C18—C19	119.8 (3)
C9—C8—C7	119.0 (3)	C14—C19—C18	119.7 (3)
C9—C8—C2	108.7 (3)

C9—O1—C1—C14	−141.6 (3)	C8—C9—C10—C11	0.0 (5)
C9—O1—C1—C2	−16.1 (3)	O1—C9—C10—C11	179.1 (3)
O1—C1—C2—C8	13.1 (3)	C9—C10—C11—C12	1.1 (5)
C14—C1—C2—C8	135.5 (3)	C10—C11—C12—N2	−179.4 (3)
O1—C1—C2—C3	130.6 (3)	C10—C11—C12—C7	−0.9 (5)
C14—C1—C2—C3	−107.0 (3)	C13—N2—C12—C11	178.4 (3)
C4—N1—C3—O2	179.1 (3)	C13—N2—C12—C7	−0.3 (4)
C4—N1—C3—C2	−4.2 (4)	C8—C7—C12—C11	−0.4 (5)
C8—C2—C3—O2	99.8 (4)	C6—C7—C12—C11	−178.8 (3)
C1—C2—C3—O2	−12.9 (4)	C8—C7—C12—N2	178.3 (3)
C8—C2—C3—N1	−76.9 (3)	C6—C7—C12—N2	−0.1 (4)
C1—C2—C3—N1	170.4 (3)	C12—N2—C13—C6	0.6 (4)
C3—N1—C4—C5	103.1 (4)	C7—C6—C13—N2	−0.7 (4)
N1—C4—C5—C6	−62.5 (4)	C5—C6—C13—N2	177.0 (3)
C4—C5—C6—C13	178.7 (3)	O1—C1—C14—C15	−7.8 (5)
C4—C5—C6—C7	−4.4 (5)	C2—C1—C14—C15	−128.3 (4)
C13—C6—C7—C12	0.4 (4)	O1—C1—C14—C19	173.9 (3)
C5—C6—C7—C12	−176.9 (3)	C2—C1—C14—C19	53.5 (4)
C13—C6—C7—C8	−177.4 (4)	C19—C14—C15—C16	−1.1 (5)
C5—C6—C7—C8	5.2 (7)	C1—C14—C15—C16	−179.4 (3)
C12—C7—C8—C9	1.5 (4)	C14—C15—C16—C17	−0.1 (5)
C6—C7—C8—C9	179.2 (4)	C15—C16—C17—O4	180.0 (3)
C12—C7—C8—C2	−173.6 (3)	C15—C16—C17—C18	1.1 (5)
C6—C7—C8—C2	4.1 (6)	C20—O3—C18—C17	−176.1 (3)
C3—C2—C8—C9	−124.7 (3)	C20—O3—C18—C19	3.4 (5)
C1—C2—C8—C9	−5.7 (3)	C16—C17—C18—O3	178.8 (3)
C3—C2—C8—C7	50.8 (5)	O4—C17—C18—O3	−0.1 (5)
C1—C2—C8—C7	169.8 (3)	C16—C17—C18—C19	−0.8 (5)
C7—C8—C9—C10	−1.4 (5)	O4—C17—C18—C19	−179.7 (3)
C2—C8—C9—C10	174.8 (3)	C15—C14—C19—C18	1.4 (5)
C7—C8—C9—O1	179.5 (3)	C1—C14—C19—C18	179.7 (3)
C2—C8—C9—O1	−4.3 (4)	O3—C18—C19—C14	180.0 (3)
C1—O1—C9—C8	13.1 (4)	C17—C18—C19—C14	−0.5 (5)
C1—O1—C9—C10	−166.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.79 (4)	2.29 (4)	3.002 (4)	150 (4)
N2—H2···O2ⁱⁱ	0.76 (4)	2.15 (4)	2.909 (4)	171 (3)
O4—H4···O3	1.00 (4)	2.17 (3)	2.631 (5)	106 (2)
C1—H1A···O2	1.00	2.27	2.794 (4)	111
C11—H11···O4ⁱⁱⁱ	0.95	2.51	3.367 (4)	150
C15—H15···O1	0.94	2.37	2.740 (4)	103

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₄
M_r	350.36
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	150
a, b, c (Å)	4.8724 (3), 15.2803 (9), 10.6940 (7)
β (°)	101.840 (3)
V (Å³)	779.25 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.4 × 0.2 × 0.05

Data collection
Diffractometer	Enraf Nonius KappaCCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5565, 1839, 1272
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.097, 0.99
No. of reflections	1839
No. of parameters	245
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

O2—C3	1.227 (4)	C7—C12	1.422 (5)
C1—C14	1.509 (5)	C8—C9	1.367 (4)
C6—C13	1.376 (5)

C13—C6—C7	105.5 (3)	C8—C7—C6	137.5 (3)
C13—C6—C5	122.6 (3)	C9—C8—C7	119.0 (3)
C7—C6—C5	131.9 (3)	C9—C8—C2	108.7 (3)
C12—C7—C8	114.9 (3)	C7—C8—C2	132.2 (3)
C12—C7—C6	107.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	.79 (4)	2.29 (4)	3.002 (4)	150 (4)
N2—H2···O2ⁱⁱ	.76 (4)	2.15 (4)	2.909 (4)	171 (3)
O4—H4···O3	1.00 (4)	2.17 (3)	2.631 (5)	106 (2)
C1—H1A···O2	1.00	2.27	2.794 (4)	111
C11—H11···O4ⁱⁱⁱ	0.95	2.51	3.367 (4)	150
C15—H15···O1	0.94	2.37	2.740 (4)	103

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

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