Crystal structure and characterization of monascin from the extracts of Monascus purpureus-fermented rice

We present a novel solid form of monascin, an aza­philonoid derivative extracted from Monascus purpureus-fermented rice. The crystal structure, C₂₁H₂₆O₅, was characterized by single-crystal X-ray diffraction and belongs to the ortho­rhom­bic space group P2₁2₁2₁. To gain insight into the electronic properties of the short contacts in the crystalline state of monascin, we utilized the Experimental Library of Multipolar Atom Model 2 (ELMAM2) database to transfer the electron density of monascin in its crystalline state. Hirshfeld surface analysis, fingerprint analysis, electronic properties and energetic characterization reveal that inter­molecular C—H⋯O hy­dro­gen bonds play a crucial role in the noncovalent bonding inter­actions by connecting mol­ecules into two- and three-dimensional networks. The mol­ecular electrostatic potential (MEP) map of the monascin mol­ecule demonstrates that negatively charged regions located at four O atoms are favoured binding sites for more positively charged amino acid residues during mol­ecular recognition. In addition, powder X-ray diffraction confirms that no transformation occurs during the crystallization of monascin.

Computing details

3-Hexanoyl-9a-methyl-6-[(E)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2H-furo[3,2-g]isochromene-2,9(3H)-dione (SHEXL-IAM)

Crystal data

C21H26O5	Dx = 1.245 Mg m^−3
Mr = 358.42	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 1329 reflections
a = 7.4153 (11) Å	θ = 3.8–22.6°
b = 9.3005 (15) Å	µ = 0.09 mm^−1
c = 27.725 (4) Å	T = 293 K
V = 1912.1 (5) Å^3	Needle, yellow
Z = 4	0.35 × 0.3 × 0.25 mm
F(000) = 768

Data collection

Agilent Xcalibur Eos diffractometer	3728 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2395 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0874 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −9→5
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = −11→7
Tmin = 0.976, Tmax = 1.000	l = −34→19
5935 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.058	w = 1/[σ^2(Fo^2) + (0.0576P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.133	(Δ/σ)max = 0.001
S = 1.00	Δρmax = 0.13 e Å^−3
3728 reflections	Δρmin = −0.16 e Å^−3
238 parameters	Absolute structure: Flack x determined using 671 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: unk
Primary atom site location: structure-invariant direct methods

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0443 (3)	0.5976 (3)	0.44726 (8)	0.0606 (7)
O2	−0.0091 (3)	0.7302 (3)	0.23385 (8)	0.0549 (7)
O3	0.1074 (4)	0.7486 (4)	0.16028 (9)	0.0745 (9)
O4	−0.1905 (3)	0.5986 (3)	0.31140 (10)	0.0662 (8)
O5	0.4846 (4)	0.5447 (4)	0.21270 (11)	0.0826 (10)
C1	0.0689 (5)	0.6107 (4)	0.36015 (12)	0.0459 (9)
C2	−0.0171 (5)	0.5384 (5)	0.40211 (13)	0.0589 (11)
H2A	−0.1469	0.5490	0.3999	0.071*
H2B	0.0107	0.4365	0.4012	0.071*
C3	0.2245 (5)	0.6147 (4)	0.45057 (14)	0.0533 (10)
C4	0.3259 (5)	0.6308 (4)	0.41123 (14)	0.0545 (10)
H4	0.4508	0.6319	0.4142	0.065*
C5	0.2469 (5)	0.6463 (4)	0.36464 (12)	0.0447 (9)
C6	0.3551 (5)	0.7060 (4)	0.32386 (12)	0.0490 (10)
H6A	0.4705	0.6572	0.3220	0.059*
H6B	0.3773	0.8076	0.3291	0.059*
C7	0.2519 (5)	0.6847 (4)	0.27766 (12)	0.0442 (9)
H7	0.2437	0.5806	0.2726	0.053*
C8	0.3082 (4)	0.7490 (4)	0.23001 (12)	0.0477 (9)
H8	0.3465	0.8488	0.2347	0.057*
C9	0.1311 (6)	0.7455 (4)	0.20278 (14)	0.0566 (10)
C10	0.0602 (5)	0.7389 (4)	0.28284 (12)	0.0444 (8)
C11	−0.0376 (5)	0.6416 (4)	0.31725 (13)	0.0478 (9)
C12	0.2921 (6)	0.6228 (5)	0.49943 (14)	0.0645 (12)
H12	0.4119	0.6495	0.5036	0.077*
C13	0.1968 (6)	0.5950 (5)	0.53839 (15)	0.0706 (13)
H13	0.0754	0.5726	0.5345	0.085*
C14	0.2705 (7)	0.5973 (6)	0.58811 (15)	0.0904 (16)
H14A	0.3942	0.6277	0.5873	0.136*
H14B	0.2633	0.5027	0.6018	0.136*
H14C	0.2018	0.6631	0.6075	0.136*
C15	0.4521 (6)	0.6671 (5)	0.20250 (14)	0.0589 (11)
C16	0.5435 (7)	0.7438 (6)	0.16311 (16)	0.0875 (15)
H16A	0.6230	0.8154	0.1771	0.105*
H16B	0.4532	0.7946	0.1444	0.105*
C17	0.6525 (7)	0.6508 (7)	0.12931 (19)	0.112 (2)
H17A	0.7721	0.6403	0.1431	0.134*
H17B	0.5979	0.5561	0.1289	0.134*
C18	0.6732 (7)	0.6954 (6)	0.08118 (18)	0.0959 (17)
H18A	0.7214	0.7924	0.0815	0.115*
H18B	0.5541	0.7005	0.0668	0.115*
C19	0.7895 (9)	0.6070 (7)	0.0487 (2)	0.125 (2)
H19A	0.9106	0.6064	0.0619	0.150*
H19B	0.7455	0.5088	0.0495	0.150*
C20	0.8001 (11)	0.6511 (9)	−0.0002 (2)	0.164 (3)
H20A	0.8624	0.5791	−0.0186	0.246*
H20B	0.8646	0.7404	−0.0023	0.246*
H20C	0.6807	0.6636	−0.0129	0.246*
C21	0.0384 (5)	0.8946 (4)	0.29906 (13)	0.0576 (10)
H21A	0.1091	0.9561	0.2786	0.086*
H21B	0.0787	0.9041	0.3318	0.086*
H21C	−0.0863	0.9217	0.2969	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0585 (15)	0.0748 (19)	0.0486 (16)	−0.0074 (16)	−0.0025 (13)	0.0008 (16)
O2	0.0607 (16)	0.0585 (17)	0.0456 (15)	0.0075 (14)	−0.0148 (13)	0.0007 (14)
O3	0.099 (2)	0.081 (2)	0.0437 (16)	0.004 (2)	−0.0175 (15)	0.0039 (17)
O4	0.0484 (15)	0.078 (2)	0.0717 (19)	−0.0073 (15)	−0.0145 (13)	0.0071 (18)
O5	0.102 (2)	0.062 (2)	0.084 (2)	0.0188 (19)	0.0267 (19)	0.0050 (18)
C1	0.049 (2)	0.044 (2)	0.045 (2)	−0.0026 (18)	−0.0036 (16)	0.001 (2)
C2	0.058 (2)	0.067 (3)	0.052 (2)	−0.013 (2)	−0.011 (2)	0.003 (2)
C3	0.063 (2)	0.049 (2)	0.048 (2)	−0.005 (2)	−0.0095 (19)	0.006 (2)
C4	0.051 (2)	0.061 (3)	0.052 (2)	−0.004 (2)	−0.0094 (19)	0.005 (2)
C5	0.049 (2)	0.043 (2)	0.042 (2)	0.0036 (19)	−0.0036 (17)	0.0015 (18)
C6	0.050 (2)	0.051 (2)	0.047 (2)	0.0032 (19)	−0.0080 (17)	0.0003 (19)
C7	0.052 (2)	0.0376 (18)	0.043 (2)	−0.0002 (18)	−0.0079 (18)	−0.0032 (18)
C8	0.063 (2)	0.0379 (19)	0.0421 (19)	−0.003 (2)	−0.0044 (17)	−0.0005 (19)
C9	0.078 (3)	0.041 (2)	0.050 (2)	0.006 (2)	−0.008 (2)	−0.001 (2)
C10	0.0517 (19)	0.042 (2)	0.0397 (18)	0.0037 (19)	−0.0119 (16)	−0.0006 (19)
C11	0.047 (2)	0.044 (2)	0.052 (2)	0.0027 (19)	−0.0054 (18)	−0.007 (2)
C12	0.076 (3)	0.064 (3)	0.054 (3)	−0.013 (2)	−0.014 (2)	0.005 (2)
C13	0.086 (3)	0.074 (3)	0.053 (3)	−0.010 (3)	−0.009 (2)	0.003 (3)
C14	0.117 (4)	0.106 (4)	0.049 (3)	−0.011 (4)	−0.006 (3)	0.008 (3)
C15	0.068 (2)	0.061 (3)	0.048 (2)	0.000 (2)	−0.001 (2)	0.003 (2)
C16	0.099 (3)	0.090 (4)	0.074 (3)	0.010 (3)	0.021 (3)	0.018 (3)
C17	0.106 (4)	0.133 (5)	0.096 (4)	0.043 (4)	0.048 (3)	0.035 (4)
C18	0.108 (4)	0.101 (4)	0.079 (4)	0.003 (3)	−0.007 (3)	0.003 (3)
C19	0.126 (5)	0.147 (6)	0.102 (5)	0.019 (5)	0.046 (4)	0.001 (5)
C20	0.195 (8)	0.180 (8)	0.117 (6)	0.001 (6)	0.041 (5)	−0.021 (6)
C21	0.074 (3)	0.044 (2)	0.055 (2)	0.009 (2)	0.001 (2)	0.000 (2)

Geometric parameters (Å, º)

O1—C2	1.441 (4)	C6—C7	1.505 (4)
O1—C3	1.349 (4)	C7—C8	1.509 (5)
O2—C9	1.358 (5)	C7—C10	1.515 (5)
O2—C10	1.454 (4)	C8—C9	1.515 (5)
O3—C9	1.192 (4)	C8—C15	1.517 (5)
O4—C11	1.214 (4)	C10—C11	1.502 (5)
O5—C15	1.197 (5)	C10—C21	1.525 (5)
C1—C2	1.488 (5)	C12—C13	1.316 (6)
C1—C5	1.366 (5)	C13—C14	1.483 (5)
C1—C11	1.456 (5)	C15—C16	1.470 (6)
C3—C4	1.333 (5)	C16—C17	1.510 (7)
C3—C12	1.446 (5)	C17—C18	1.406 (6)
C4—C5	1.426 (5)	C18—C19	1.493 (7)
C5—C6	1.494 (5)	C19—C20	1.420 (8)
C3—O1—C2	114.6 (3)	O3—C9—O2	121.1 (4)
C9—O2—C10	108.4 (3)	O3—C9—C8	128.3 (4)
C5—C1—C2	116.9 (3)	O2—C10—C7	103.0 (3)
C5—C1—C11	123.4 (3)	O2—C10—C11	112.9 (3)
C11—C1—C2	119.7 (3)	O2—C10—C21	106.9 (3)
O1—C2—C1	111.8 (3)	C7—C10—C21	116.3 (3)
O1—C3—C12	114.4 (4)	C11—C10—C7	108.2 (3)
C4—C3—O1	121.1 (3)	C11—C10—C21	109.5 (3)
C4—C3—C12	124.4 (4)	O4—C11—C1	123.4 (3)
C3—C4—C5	121.4 (3)	O4—C11—C10	124.4 (3)
C1—C5—C4	117.1 (3)	C1—C11—C10	112.1 (3)
C1—C5—C6	122.7 (3)	C13—C12—C3	124.9 (4)
C4—C5—C6	120.2 (3)	C12—C13—C14	124.2 (4)
C5—C6—C7	108.8 (3)	O5—C15—C8	120.0 (4)
C6—C7—C8	123.5 (3)	O5—C15—C16	123.0 (4)
C6—C7—C10	110.6 (3)	C16—C15—C8	117.0 (4)
C8—C7—C10	102.1 (3)	C15—C16—C17	115.4 (5)
C7—C8—C9	100.9 (3)	C18—C17—C16	118.6 (5)
C7—C8—C15	115.8 (3)	C17—C18—C19	118.2 (5)
C9—C8—C15	110.4 (3)	C20—C19—C18	116.7 (6)
O2—C9—C8	110.5 (3)
O1—C3—C4—C5	6.9 (6)	C7—C8—C9—O3	−158.7 (5)
O1—C3—C12—C13	9.9 (7)	C7—C8—C15—O5	16.9 (6)
O2—C10—C11—O4	−24.2 (5)	C7—C8—C15—C16	−164.4 (4)
O2—C10—C11—C1	159.0 (3)	C7—C10—C11—O4	−137.5 (4)
O5—C15—C16—C17	12.5 (7)	C7—C10—C11—C1	45.7 (4)
C1—C5—C6—C7	−13.6 (5)	C8—C7—C10—O2	38.6 (3)
C2—O1—C3—C4	25.1 (5)	C8—C7—C10—C11	158.3 (3)
C2—O1—C3—C12	−158.6 (3)	C8—C7—C10—C21	−78.0 (4)
C2—C1—C5—C4	−9.2 (5)	C8—C15—C16—C17	−166.2 (4)
C2—C1—C5—C6	173.8 (3)	C9—O2—C10—C7	−28.2 (4)
C2—C1—C11—O4	−7.8 (6)	C9—O2—C10—C11	−144.7 (3)
C2—C1—C11—C10	169.0 (3)	C9—O2—C10—C21	94.8 (3)
C3—O1—C2—C1	−46.6 (4)	C9—C8—C15—O5	−96.9 (5)
C3—C4—C5—C1	−15.0 (6)	C9—C8—C15—C16	81.9 (5)
C3—C4—C5—C6	162.1 (4)	C10—O2—C9—O3	−176.6 (4)
C3—C12—C13—C14	177.1 (4)	C10—O2—C9—C8	6.4 (4)
C4—C3—C12—C13	−173.9 (5)	C10—C7—C8—C9	−33.7 (3)
C4—C5—C6—C7	169.5 (3)	C10—C7—C8—C15	−152.9 (3)
C5—C1—C2—O1	38.9 (5)	C11—C1—C2—O1	−140.4 (3)
C5—C1—C11—O4	173.0 (4)	C11—C1—C5—C4	170.1 (3)
C5—C1—C11—C10	−10.2 (5)	C11—C1—C5—C6	−6.9 (6)
C5—C6—C7—C8	171.6 (3)	C12—C3—C4—C5	−169.0 (4)
C5—C6—C7—C10	50.3 (4)	C15—C8—C9—O2	141.1 (3)
C6—C7—C8—C9	−158.9 (3)	C15—C8—C9—O3	−35.7 (6)
C6—C7—C8—C15	82.0 (4)	C15—C16—C17—C18	150.9 (5)
C6—C7—C10—O2	171.8 (3)	C16—C17—C18—C19	176.7 (5)
C6—C7—C10—C11	−68.5 (4)	C17—C18—C19—C20	176.9 (6)
C6—C7—C10—C21	55.2 (4)	C21—C10—C11—O4	94.8 (4)
C7—C8—C9—O2	18.1 (4)	C21—C10—C11—C1	−82.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4	0.97	2.52	2.880 (5)	102
C2—H2B···O3^i	0.97	2.59	3.272 (6)	127
C6—H6A···O4^ii	0.97	2.59	3.531 (4)	164
C7—H7···O5	0.98	2.46	2.814 (5)	101
C13—H13···O1	0.93	2.44	2.768 (5)	101
C17—H17B···O5	0.97	2.47	2.805 (6)	100

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

(3S,3aR,9aR)-3-Hexanoyl-9a-methyl-6-[(E)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2H-furo[3,2-g]isochromene-2,9(3H)-dione (MoPro-IAM)

Crystal data

C21H26O5	F(000) = 768
Mr = 358.41	Dx = 1.245 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1329 reflections
a = 7.4153 (11) Å	θ = 3.8–22.6°
b = 9.3005 (15) Å	µ = 0.09 mm^−1
c = 27.725 (4) Å	T = 293 K
V = 1912.1 (5) Å^3	Needel, yellow
Z = 4	0.35 × 0.3 × 0.25 mm

Data collection

Agilent Xcalibur Eos diffractometer	3452 independent reflections
Radiation source: fine-focus sealed tube	2383 reflections with I > 2 σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0874 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = 0→11
Tmin = 0.976, Tmax = 1.000	l = 0→34
3716 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.132	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.P] where P = (Fo^2 + 2Fc^2)/3
S = 1.02	(Δ/σ)max < 0.001
3452 reflections	Δρmax = 0.34 e Å^−3
235 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Absolute structure: Flack x determined using 671 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.6 (9)

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0443 (3)	0.5978 (3)	0.44721 (7)	0.0610 (3)
O2	−0.0089 (3)	0.7302 (2)	0.23389 (7)	0.0550 (3)
O3	0.1074 (3)	0.7488 (3)	0.16020 (8)	0.0751 (5)
O4	−0.1906 (3)	0.5986 (3)	0.31140 (8)	0.0663 (3)
O5	0.4844 (4)	0.5448 (3)	0.21271 (10)	0.0837 (5)
C1	0.0691 (4)	0.6109 (4)	0.36009 (11)	0.0464 (4)
C2	−0.0172 (4)	0.5377 (4)	0.40209 (12)	0.0596 (5)
H2A	−0.14690	0.54900	0.39990	0.07100*
H2B	0.01070	0.43650	0.40120	0.07100*
C3	0.2246 (5)	0.6144 (3)	0.45058 (12)	0.0538 (5)
C4	0.3260 (4)	0.6305 (4)	0.41121 (12)	0.0552 (5)
H4	0.45080	0.63190	0.41420	0.06500*
C5	0.2468 (4)	0.6462 (3)	0.36465 (11)	0.0446 (4)
C6	0.3558 (4)	0.7062 (4)	0.32391 (11)	0.0492 (4)
H6A	0.47050	0.65720	0.32200	0.05900*
H6B	0.37730	0.80760	0.32910	0.05900*
C7	0.2518 (4)	0.6847 (3)	0.27765 (10)	0.0443 (4)
H7	0.24370	0.58060	0.27260	0.05300*
C8	0.3085 (4)	0.7493 (3)	0.23006 (10)	0.0479 (5)
H8	0.34650	0.84880	0.23470	0.05700*
C9	0.1308 (5)	0.7455 (4)	0.20286 (12)	0.0566 (5)
C10	0.0603 (4)	0.7388 (3)	0.28284 (10)	0.0447 (4)
C11	−0.0375 (4)	0.6416 (3)	0.31717 (12)	0.0480 (4)
C12	0.2919 (5)	0.6233 (4)	0.49953 (13)	0.0644 (6)
H12	0.41190	0.64950	0.50360	0.07700*
C13	0.1968 (5)	0.5949 (4)	0.53834 (13)	0.0715 (6)
H13	0.07540	0.57260	0.53450	0.08500*
C14	0.2705 (6)	0.5975 (5)	0.58829 (13)	0.0907 (8)
H14A	0.39420	0.62770	0.58730	0.13600*
H14B	0.26330	0.50270	0.60180	0.13600*
H14C	0.20180	0.66310	0.60750	0.13600*
C15	0.4525 (5)	0.6676 (4)	0.20250 (12)	0.0595 (5)
C16	0.5433 (6)	0.7446 (5)	0.16317 (14)	0.0891 (7)
H16A	0.62300	0.81540	0.17710	0.10500*
H16B	0.45320	0.79460	0.14440	0.10500*
C17	0.6520 (6)	0.6493 (6)	0.12939 (17)	0.1132 (9)
H17A	0.77210	0.64030	0.14310	0.13400*
H17B	0.59790	0.55610	0.12890	0.13400*
C18	0.6732 (6)	0.6957 (5)	0.08094 (17)	0.0974 (9)
H18A	0.72140	0.79240	0.08150	0.11500*
H18B	0.55410	0.70050	0.06680	0.11500*
C19	0.7893 (7)	0.6074 (6)	0.0488 (2)	0.1244 (10)
H19A	0.91060	0.60640	0.06190	0.15000*
H19B	0.74550	0.50880	0.04950	0.15000*
C20	0.8013 (11)	0.6517 (8)	−0.0003 (2)	0.1658 (17)
H20A	0.86240	0.57910	−0.01860	0.24600*
H20B	0.86460	0.74040	−0.00230	0.24600*
H20C	0.68070	0.66360	−0.01290	0.24600*
C21	0.0384 (5)	0.8950 (4)	0.29906 (11)	0.0586 (5)
H21A	0.10910	0.95610	0.27860	0.08600*
H21B	0.07870	0.90410	0.33180	0.08600*
H21C	−0.08630	0.92170	0.29690	0.08600*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0596 (13)	0.0747 (16)	0.0487 (13)	−0.0072 (13)	−0.0031 (11)	0.0014 (14)
O2	0.0613 (14)	0.0577 (14)	0.0461 (12)	0.0070 (12)	−0.0148 (11)	0.0009 (12)
O3	0.0998 (19)	0.0812 (19)	0.0441 (13)	0.0030 (17)	−0.0182 (13)	0.0031 (15)
O4	0.0473 (13)	0.0795 (17)	0.0720 (16)	−0.0074 (12)	−0.0151 (11)	0.0073 (15)
O5	0.104 (2)	0.0617 (17)	0.0859 (19)	0.0192 (16)	0.0278 (16)	0.0051 (15)
C1	0.0471 (17)	0.0457 (18)	0.0464 (17)	0.0000 (16)	−0.0048 (14)	0.0003 (17)
C2	0.059 (2)	0.071 (2)	0.0492 (19)	−0.0149 (18)	−0.0099 (17)	0.0052 (19)
C3	0.063 (2)	0.049 (2)	0.0499 (19)	−0.0062 (18)	−0.0096 (17)	0.0062 (19)
C4	0.0534 (18)	0.060 (2)	0.052 (2)	−0.0053 (17)	−0.0082 (16)	0.0043 (19)
C5	0.0494 (17)	0.0419 (17)	0.0425 (17)	0.0041 (16)	−0.0033 (14)	0.0011 (15)
C6	0.0502 (17)	0.0533 (19)	0.0441 (18)	0.0022 (16)	−0.0077 (15)	0.0005 (16)
C7	0.0512 (17)	0.0394 (16)	0.0422 (16)	0.0007 (15)	−0.0070 (15)	−0.0025 (15)
C8	0.0626 (19)	0.0396 (16)	0.0415 (16)	−0.0025 (17)	−0.0043 (14)	0.0007 (16)
C9	0.078 (2)	0.0403 (18)	0.0512 (19)	0.004 (2)	−0.0065 (19)	−0.0009 (18)
C10	0.0514 (16)	0.0422 (17)	0.0405 (15)	0.0026 (16)	−0.0123 (13)	−0.0009 (16)
C11	0.0479 (17)	0.0441 (17)	0.0520 (18)	0.0034 (16)	−0.0042 (16)	−0.0072 (17)
C12	0.078 (2)	0.063 (2)	0.052 (2)	−0.013 (2)	−0.0132 (18)	0.004 (2)
C13	0.089 (3)	0.073 (3)	0.053 (2)	−0.011 (2)	−0.0069 (19)	0.002 (2)
C14	0.118 (3)	0.107 (3)	0.047 (2)	−0.012 (3)	−0.008 (2)	0.006 (3)
C15	0.069 (2)	0.061 (2)	0.0492 (19)	−0.002 (2)	−0.0023 (18)	0.0016 (19)
C16	0.102 (3)	0.093 (3)	0.073 (2)	0.012 (3)	0.025 (2)	0.021 (3)
C17	0.111 (3)	0.133 (4)	0.096 (3)	0.043 (3)	0.050 (3)	0.032 (3)
C18	0.111 (3)	0.104 (4)	0.078 (3)	0.005 (3)	−0.007 (3)	0.002 (3)
C19	0.125 (4)	0.147 (5)	0.102 (4)	0.017 (4)	0.046 (3)	0.000 (4)
C20	0.201 (7)	0.183 (7)	0.114 (5)	0.001 (5)	0.038 (4)	−0.017 (5)
C21	0.075 (2)	0.0438 (19)	0.057 (2)	0.0108 (18)	0.0023 (18)	−0.0008 (18)

Geometric parameters (Å, º)

O1—C3	1.350 (4)	C10—C21	1.529 (5)
O1—C2	1.444 (4)	C12—C13	1.313 (5)
O2—C9	1.354 (4)	C12—H12	0.9294
O2—C10	1.453 (3)	C13—C14	1.489 (5)
O3—C9	1.196 (4)	C13—H13	0.9297
O4—C11	1.214 (3)	C14—H14C	0.9568
O5—C15	1.201 (4)	C14—H14B	0.9594
C1—C11	1.456 (4)	C14—H14A	0.9596
C1—C2	1.493 (4)	C15—C16	1.468 (5)
C1—C5	1.364 (4)	C16—C17	1.521 (6)
C2—H2B	0.9639	C16—H16A	0.9658
C2—H2A	0.9692	C16—H16B	0.9659
C3—C4	1.334 (5)	C17—C18	1.420 (6)
C3—C12	1.448 (4)	C17—H17B	0.9550
C4—C5	1.426 (4)	C17—H17A	0.9720
C4—H4	0.9291	C18—C19	1.487 (7)
C5—C6	1.497 (4)	C18—H18B	0.9675
C6—C7	1.510 (4)	C18—H18A	0.9681
C6—H6A	0.9666	C19—C20	1.425 (7)
C6—H6B	0.9669	C19—H19A	0.9702
C7—C10	1.514 (4)	C19—H19B	0.9728
C7—C8	1.510 (4)	C20—H20B	0.9506
C7—H7	0.9800	C20—H20A	0.9583
C8—C9	1.518 (4)	C20—H20C	0.9665
C8—C15	1.518 (5)	C21—H21C	0.9591
C8—H8	0.9756	C21—H21A	0.9593
C10—C11	1.500 (4)	C21—H21B	0.9594
C3—O1—C2	114.7 (2)	C3—C12—H12	117.3 (3)
C9—O2—C10	108.5 (2)	C13—C12—H12	117.9 (3)
C11—C1—C2	119.6 (2)	C12—C13—C14	124.2 (3)
C11—C1—C5	123.6 (2)	C12—C13—H13	118.1 (3)
C2—C1—C5	116.8 (2)	C14—C13—H13	117.7 (3)
O1—C2—C1	111.3 (2)	C13—C14—H14C	109.4 (3)
O1—C2—H2B	109.4 (3)	C13—C14—H14B	109.1 (3)
O1—C2—H2A	109.0 (3)	C13—C14—H14A	109.2 (3)
C1—C2—H2B	109.5 (3)	H14C—C14—H14B	109.8 (4)
C1—C2—H2A	109.1 (3)	H14C—C14—H14A	109.8 (4)
H2B—C2—H2A	108.5 (3)	H14B—C14—H14A	109.5 (4)
O1—C3—C4	121.0 (3)	O5—C15—C8	119.8 (3)
O1—C3—C12	114.4 (3)	O5—C15—C16	123.3 (3)
C4—C3—C12	124.5 (3)	C8—C15—C16	116.9 (3)
C3—C4—C5	121.3 (3)	C15—C16—C17	114.6 (3)
C3—C4—H4	119.3 (3)	C15—C16—H16A	108.4 (3)
C5—C4—H4	119.3 (3)	C15—C16—H16B	108.6 (3)
C1—C5—C6	122.8 (2)	C17—C16—H16A	108.6 (4)
C1—C5—C4	117.2 (2)	C17—C16—H16B	108.4 (4)
C6—C5—C4	119.9 (2)	H16A—C16—H16B	108.1 (4)
C7—C6—C5	108.4 (2)	C18—C17—C16	117.7 (4)
C7—C6—H6A	109.9 (2)	C18—C17—H17B	108.0 (4)
C7—C6—H6B	109.9 (2)	C18—C17—H17A	107.1 (4)
C5—C6—H6A	109.9 (2)	C16—C17—H17B	108.4 (4)
C5—C6—H6B	109.9 (2)	C16—C17—H17A	107.2 (4)
H6A—C6—H6B	108.8 (3)	H17B—C17—H17A	108.2 (4)
C10—C7—C8	102.2 (2)	C17—C18—C19	117.6 (4)
C10—C7—C6	110.7 (2)	C17—C18—H18B	107.2 (4)
C10—C7—H7	106.5 (2)	C17—C18—H18A	107.9 (4)
C8—C7—C6	123.2 (2)	C19—C18—H18B	108.1 (4)
C8—C7—H7	106.6 (2)	C19—C18—H18A	108.0 (4)
C6—C7—H7	106.5 (2)	H18B—C18—H18A	107.5 (4)
C9—C8—C15	110.4 (2)	C18—C19—C20	116.7 (4)
C9—C8—C7	100.6 (2)	C18—C19—H19A	108.5 (4)
C9—C8—H8	109.8 (2)	C18—C19—H19B	108.4 (4)
C15—C8—C7	115.9 (2)	C20—C19—H19A	107.6 (5)
C15—C8—H8	109.7 (3)	C20—C19—H19B	108.2 (5)
C7—C8—H8	110.1 (2)	H19A—C19—H19B	107.0 (5)
O2—C9—O3	121.4 (3)	C19—C20—H20B	109.7 (6)
O2—C9—C8	110.5 (2)	C19—C20—H20A	109.3 (5)
O3—C9—C8	128.0 (3)	C19—C20—H20C	108.7 (6)
O2—C10—C11	112.9 (2)	H20B—C20—H20A	110.3 (6)
O2—C10—C7	102.9 (2)	H20B—C20—H20C	109.7 (7)
O2—C10—C21	106.8 (2)	H20A—C20—H20C	109.1 (6)
C11—C10—C7	108.3 (2)	C10—C21—H21C	109.3 (3)
C11—C10—C21	109.5 (2)	C10—C21—H21A	109.3 (3)
C7—C10—C21	116.3 (2)	C10—C21—H21B	109.2 (3)
O4—C11—C10	124.5 (3)	H21C—C21—H21A	109.7 (3)
O4—C11—C1	123.4 (2)	H21C—C21—H21B	109.7 (3)
C10—C11—C1	112.0 (2)	H21A—C21—H21B	109.7 (3)
C3—C12—C13	124.8 (3)
O1—C3—C4—C5	6.8 (4)	H6A—C6—C7—H7	55.06
O1—C3—C4—H4	−173.49	H6B—C6—C7—C10	−69.78
O1—C3—C12—C13	10.9 (5)	H6B—C6—C7—C8	51.45
O1—C3—C12—H12	−170.35	H6B—C6—C7—H7	174.80
O1—C2—C1—C11	−140.3 (4)	C7—C10—O2—C9	−28.2 (4)
O1—C2—C1—C5	39.3 (4)	C7—C10—C21—H21C	172.17
O2—C9—C8—C15	141.1 (4)	C7—C10—C21—H21A	52.15
O2—C9—C8—C7	18.2 (4)	C7—C10—C21—H21B	−67.85
O2—C9—C8—H8	−97.72	C7—C8—C15—C16	−164.6 (5)
O2—C10—C11—O4	−24.3 (4)	H7—C7—C10—C11	46.75
O2—C10—C11—C1	159.1 (4)	H7—C7—C10—C21	170.57
O2—C10—C7—C8	38.6 (4)	H7—C7—C8—C9	77.76
O2—C10—C7—C6	171.6 (4)	H7—C7—C8—C15	−41.26
O2—C10—C7—H7	−73.02	H7—C7—C8—H8	−166.48
O2—C10—C21—H21C	57.93	C8—C9—O2—C10	6.2 (4)
O2—C10—C21—H21A	−62.09	C8—C15—C16—C17	−166.0 (5)
O2—C10—C21—H21B	177.91	C8—C15—C16—H16A	72.46
O3—C9—O2—C10	−176.6 (4)	C8—C15—C16—H16B	−44.73
O3—C9—C8—C15	−35.8 (4)	C8—C7—C10—C11	158.4 (4)
O3—C9—C8—C7	−158.7 (4)	C8—C7—C10—C21	−77.8 (4)
O3—C9—C8—H8	85.35	H8—C8—C15—C16	−39.27
O4—C11—C10—C7	−137.6 (4)	H8—C8—C7—C10	81.92
O4—C11—C10—C21	94.6 (4)	C9—O2—C10—C11	−144.7 (4)
O4—C11—C1—C2	−7.3 (4)	C9—O2—C10—C21	94.8 (4)
O4—C11—C1—C5	173.0 (4)	C9—C8—C15—C16	81.9 (5)
O5—C15—C8—C9	−96.5 (4)	C9—C8—C7—C10	−33.8 (4)
O5—C15—C8—C7	17.0 (4)	C10—C7—C8—C15	−152.9 (4)
O5—C15—C8—H8	142.33	C11—C10—C21—H21C	−64.67
O5—C15—C16—C17	12.3 (5)	C11—C10—C21—H21A	175.31
O5—C15—C16—H16A	−109.20	C11—C10—C21—H21B	55.31
O5—C15—C16—H16B	133.61	C12—C13—C14—H14C	123.15
C1—C11—C10—C7	45.8 (4)	C12—C13—C14—H14B	−116.67
C1—C11—C10—C21	−82.0 (4)	C12—C13—C14—H14A	2.97
C1—C2—O1—C3	−47.3 (4)	H12—C12—C13—C14	−1.97
C1—C5—C6—C7	−13.7 (4)	H12—C12—C13—H13	177.37
C1—C5—C6—H6A	−133.81	H13—C13—C14—H14C	−56.20
C1—C5—C6—H6B	106.41	H13—C13—C14—H14B	63.99
C1—C5—C4—C3	−15.0 (4)	H13—C13—C14—H14A	−176.37
C1—C5—C4—H4	165.30	C15—C16—C17—C18	151.7 (6)
C2—O1—C3—C4	25.7 (4)	C15—C16—C17—H17B	28.89
C2—O1—C3—C12	−158.6 (4)	C15—C16—C17—H17A	−87.67
C2—C1—C11—C10	169.3 (4)	C16—C17—C18—C19	176.1 (7)
C2—C1—C5—C6	173.7 (5)	C16—C17—C18—H18B	−61.84
C2—C1—C5—C4	−9.4 (4)	C16—C17—C18—H18A	53.69
H2A—C2—O1—C3	−167.61	H16A—C16—C17—C18	−86.94
H2A—C2—C1—C11	−20.02	H16A—C16—C17—H17B	150.28
H2A—C2—C1—C5	159.66	H16A—C16—C17—H17A	33.72
H2B—C2—O1—C3	73.87	H16B—C16—C17—C18	30.27
H2B—C2—C1—C11	98.57	H16B—C16—C17—H17B	−92.52
H2B—C2—C1—C5	−81.74	H16B—C16—C17—H17A	150.92
C3—C4—C5—C6	162.0 (4)	C17—C18—C19—C20	176.9 (7)
C3—C12—C13—C14	176.8 (5)	C17—C18—C19—H19A	−61.44
C3—C12—C13—H13	−3.86	C17—C18—C19—H19B	54.45
C4—C3—C12—C13	−173.5 (5)	H17A—C17—C18—C19	55.46
C4—C3—C12—H12	5.27	H17A—C17—C18—H18B	177.48
C4—C5—C1—C11	170.3 (4)	H17A—C17—C18—H18A	−66.99
C4—C5—C6—C7	169.4 (4)	H17B—C17—C18—C19	−60.89
C4—C5—C6—H6A	49.32	H17B—C17—C18—H18B	61.13
C4—C5—C6—H6B	−70.46	H17B—C17—C18—H18A	176.66
H4—C4—C3—C12	11.17	C18—C19—C20—H20B	68.35
H4—C4—C5—C6	−17.66	C18—C19—C20—H20A	−170.52
C5—C1—C11—C10	−10.3 (4)	C18—C19—C20—H20C	−51.55
C5—C6—C7—C10	50.3 (4)	H18A—C18—C19—C20	−60.72
C5—C6—C7—C8	171.6 (5)	H18A—C18—C19—H19A	60.98
C5—C6—C7—H7	−65.07	H18A—C18—C19—H19B	176.86
C5—C4—C3—C12	−168.5 (4)	H18B—C18—C19—C20	55.32
C6—C7—C10—C11	−68.6 (4)	H18B—C18—C19—H19A	177.01
C6—C7—C10—C21	55.2 (4)	H18B—C18—C19—H19B	−67.11
C6—C7—C8—C9	−158.9 (4)	H19A—C19—C20—H20B	−53.80
C6—C7—C8—C15	82.0 (4)	H19A—C19—C20—H20A	67.33
C6—C7—C8—H8	−43.17	H19A—C19—C20—H20C	−173.70
C6—C5—C1—C11	−6.7 (4)	H19B—C19—C20—H20B	−169.17
H6A—C6—C7—C10	170.48	H19B—C19—C20—H20A	−48.04
H6A—C6—C7—C8	−68.30	H19B—C19—C20—H20C	70.93

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3^i	0.96	2.59 (1)	3.264 (5)	127 (1)
C2—H2A···O4	0.97	2.52 (1)	2.880 (4)	102 (1)
C7—H7···O5	0.98	2.46 (1)	2.812 (4)	101 (1)
C13—H13···O1	0.93	2.44 (1)	2.768 (4)	101 (1)
C6—H6A···O4^ii	0.97	2.59 (1)	3.526 (4)	164 (1)

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

(3S,3aR,9aR)-3-Hexanoyl-9a-methyl-6-[(E)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2H-furo[3,2-g]isochromene-2,9(3H)-dione (MoPro-ELMAM2)

Crystal data

C21H26O5	F(000) = 768
Mr = 358.41	Dx = 1.245 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1329 reflections
a = 7.4153 (11) Å	θ = 3.8–22.6°
b = 9.3005 (15) Å	µ = 0.09 mm^−1
c = 27.725 (4) Å	T = 293 K
V = 1912.1 (5) Å^3	Needel, yellow
Z = 4	0.35 × 0.3 × 0.25 mm

Data collection

Agilent Xcalibur Eos diffractometer	3441 independent reflections
Radiation source: fine-focus sealed tube	2371 reflections with I > 2 σ(I)
Graphite monochromator	Rint = 0.022
Detector resolution: 16.0874 pixels mm^-1	θmax = 26.4°, θmin = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014)	k = 0→11
Tmin = 0.976, Tmax = 1.000	l = 0→34
3705 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0576P)^2 + 0.P] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max < 0.001
3441 reflections	Δρmax = 0.33 e Å^−3
261 parameters	Δρmin = −0.28 e Å^−3
0 restraints	Absolute structure: Flack x determined using 671 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.6 (9)

Special details

Refinement. Refinement of F² against reflections. The threshold expression of F² > 2sigma(F²) is used for calculating R-factors(gt) 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0447 (3)	0.5974 (3)	0.44709 (7)	0.0557 (4)
O2	−0.0088 (3)	0.7301 (2)	0.23402 (7)	0.0502 (3)
O3	0.1076 (3)	0.7483 (3)	0.16046 (8)	0.0733 (4)
O4	−0.1908 (3)	0.5988 (3)	0.31141 (8)	0.0623 (4)
O5	0.4846 (4)	0.5445 (3)	0.21274 (10)	0.0782 (5)
C1	0.0691 (4)	0.6109 (3)	0.36019 (11)	0.0435 (4)
C2	−0.0171 (4)	0.5380 (4)	0.40254 (12)	0.0538 (5)
H2A	−0.16319	0.55042	0.39963	0.07100*
H2B	0.01431	0.42342	0.40109	0.07100*
C3	0.2232 (5)	0.6145 (3)	0.45055 (12)	0.0500 (5)
C4	0.3283 (4)	0.6307 (4)	0.41113 (12)	0.0505 (5)
H4	0.47370	0.63216	0.41475	0.06500*
C5	0.2470 (4)	0.6467 (3)	0.36466 (10)	0.0419 (4)
C6	0.3551 (4)	0.7063 (3)	0.32384 (10)	0.0459 (4)
H6A	0.48482	0.65108	0.32176	0.05900*
H6B	0.38007	0.82068	0.32977	0.05900*
C7	0.2514 (4)	0.6843 (3)	0.27765 (10)	0.0403 (4)
H7	0.24269	0.56760	0.27197	0.05300*
C8	0.3076 (4)	0.7496 (3)	0.23017 (10)	0.0450 (4)
H8	0.35133	0.86144	0.23529	0.05700*
C9	0.1309 (5)	0.7453 (3)	0.20272 (12)	0.0530 (5)
C10	0.0602 (4)	0.7393 (3)	0.28276 (10)	0.0420 (4)
C11	−0.0376 (4)	0.6416 (3)	0.31719 (11)	0.0438 (4)
C12	0.2936 (5)	0.6231 (4)	0.49951 (12)	0.0602 (6)
H12	0.43323	0.65415	0.50432	0.07700*
C13	0.1955 (5)	0.5953 (4)	0.53857 (13)	0.0671 (6)
H13	0.05437	0.56874	0.53383	0.08500*
C14	0.2687 (6)	0.5972 (5)	0.58839 (13)	0.0869 (8)
H14A	0.40988	0.63153	0.58717	0.13600*
H14B	0.26225	0.48887	0.60377	0.13600*
H14C	0.19140	0.67303	0.61041	0.13600*
C15	0.4520 (5)	0.6662 (4)	0.20247 (12)	0.0563 (5)
C16	0.5428 (6)	0.7445 (5)	0.16290 (14)	0.0839 (7)
H16A	0.63297	0.82426	0.17884	0.10500*
H16B	0.44086	0.80145	0.14183	0.10500*
C17	0.6526 (6)	0.6502 (6)	0.12929 (18)	0.1086 (9)
H17A	0.78719	0.63918	0.14482	0.13400*
H17B	0.59067	0.54362	0.12883	0.13400*
C18	0.6736 (6)	0.6964 (5)	0.08126 (16)	0.0857 (8)
H18A	0.72794	0.80554	0.08158	0.11500*
H18B	0.53945	0.70110	0.06506	0.11500*
C19	0.7901 (8)	0.6080 (7)	0.0481 (2)	0.1239 (10)
H19A	0.92553	0.60628	0.06351	0.15000*
H19B	0.74049	0.49753	0.04958	0.15000*
C20	0.8011 (10)	0.6522 (8)	−0.0013 (2)	0.1471 (16)
H20A	0.87174	0.56800	−0.02139	0.24600*
H20B	0.87452	0.75429	−0.00260	0.24600*
H20C	0.66325	0.66532	−0.01472	0.24600*
C21	0.0381 (4)	0.8944 (3)	0.29903 (11)	0.0539 (5)
H21A	0.11882	0.96450	0.27579	0.08600*
H21B	0.08431	0.90537	0.33636	0.08600*
H21C	−0.10400	0.92550	0.29659	0.08600*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0546 (14)	0.0693 (15)	0.0431 (13)	−0.0072 (12)	−0.0014 (10)	0.0014 (13)
O2	0.0547 (14)	0.0539 (14)	0.0421 (13)	0.0070 (11)	−0.0141 (11)	0.0015 (11)
O3	0.0935 (18)	0.0826 (19)	0.0437 (14)	0.0042 (16)	−0.0168 (12)	0.0045 (14)
O4	0.0458 (14)	0.0752 (17)	0.0660 (16)	−0.0073 (12)	−0.0159 (10)	0.0070 (14)
O5	0.100 (2)	0.0551 (18)	0.0798 (19)	0.0219 (15)	0.0274 (15)	0.0073 (15)
C1	0.0432 (16)	0.0466 (18)	0.0408 (17)	−0.0044 (15)	−0.0062 (13)	0.0031 (16)
C2	0.0541 (19)	0.060 (2)	0.0470 (18)	−0.0133 (17)	−0.0075 (16)	0.0060 (17)
C3	0.064 (2)	0.0463 (18)	0.0400 (18)	−0.0048 (17)	−0.0082 (16)	0.0046 (17)
C4	0.0468 (17)	0.062 (2)	0.0431 (19)	−0.0043 (16)	−0.0084 (15)	0.0054 (17)
C5	0.0446 (17)	0.0441 (16)	0.0370 (16)	0.0006 (15)	−0.0048 (14)	0.0033 (15)
C6	0.0463 (16)	0.0502 (19)	0.0411 (17)	0.0026 (15)	−0.0076 (14)	0.0024 (15)
C7	0.0471 (16)	0.0345 (15)	0.0393 (16)	−0.0012 (14)	−0.0082 (14)	−0.0015 (14)
C8	0.0602 (19)	0.0358 (16)	0.0390 (16)	−0.0019 (16)	−0.0051 (14)	−0.0004 (15)
C9	0.074 (2)	0.0450 (17)	0.0404 (19)	0.005 (2)	−0.0100 (18)	0.0011 (17)
C10	0.0470 (15)	0.0393 (17)	0.0395 (16)	0.0049 (15)	−0.0106 (13)	−0.0009 (15)
C11	0.0402 (18)	0.0466 (17)	0.0446 (17)	−0.0002 (16)	−0.0092 (14)	−0.0021 (16)
C12	0.072 (2)	0.066 (2)	0.042 (2)	−0.014 (2)	−0.0146 (17)	0.0072 (18)
C13	0.081 (2)	0.076 (2)	0.044 (2)	−0.011 (2)	−0.0096 (18)	0.003 (2)
C14	0.115 (3)	0.102 (3)	0.044 (2)	−0.007 (3)	−0.009 (2)	0.006 (2)
C15	0.067 (2)	0.058 (3)	0.0440 (18)	0.0026 (19)	0.0048 (17)	0.0030 (18)
C16	0.098 (3)	0.086 (3)	0.068 (2)	0.007 (3)	0.022 (2)	0.020 (3)
C17	0.103 (3)	0.130 (4)	0.093 (4)	0.043 (3)	0.050 (3)	0.033 (3)
C18	0.096 (3)	0.091 (3)	0.070 (3)	0.005 (3)	−0.004 (2)	0.000 (3)
C19	0.115 (4)	0.145 (5)	0.112 (5)	0.016 (4)	0.039 (3)	0.000 (4)
C20	0.177 (6)	0.170 (6)	0.095 (5)	0.001 (5)	0.042 (4)	−0.014 (4)
C21	0.071 (2)	0.0393 (17)	0.0518 (19)	0.0092 (17)	0.0016 (16)	−0.0007 (16)

Geometric parameters (Å, º)

O1—C3	1.337 (4)	C10—C21	1.520 (4)
O1—C2	1.428 (4)	C12—C13	1.330 (5)
O2—C9	1.359 (4)	C12—H12	1.0830
O2—C10	1.448 (3)	C13—C14	1.484 (5)
O3—C9	1.185 (4)	C13—H13	1.0830
O4—C11	1.215 (3)	C14—H14B	1.0950
O5—C15	1.192 (4)	C14—H14C	1.0950
C1—C11	1.459 (4)	C14—H14A	1.0950
C1—C2	1.499 (4)	C15—C16	1.479 (5)
C1—C5	1.366 (4)	C16—C17	1.517 (6)
C2—H2B	1.0920	C16—H16B	1.0920
C2—H2A	1.0920	C16—H16A	1.0920
C3—C4	1.351 (4)	C17—C18	1.408 (6)
C3—C12	1.456 (4)	C17—H17A	1.0920
C4—C5	1.430 (4)	C17—H17B	1.0920
C4—H4	1.0830	C18—C19	1.507 (7)
C5—C6	1.494 (4)	C18—H18A	1.0920
C6—C7	1.508 (4)	C18—H18B	1.0920
C6—H6B	1.0920	C19—C20	1.431 (8)
C6—H6A	1.0920	C19—H19B	1.0920
C7—C10	1.514 (4)	C19—H19A	1.0920
C7—C8	1.508 (4)	C20—H20A	1.0950
C7—H7	1.0990	C20—H20C	1.0950
C8—C9	1.516 (4)	C20—H20B	1.0950
C8—C15	1.529 (5)	C21—H21B	1.0950
C8—H8	1.0990	C21—H21C	1.0950
C10—C11	1.504 (4)	C21—H21A	1.0950
C3—O1—C2	115.2 (2)	C3—C12—H12	118.2 (3)
C9—O2—C10	108.7 (2)	C13—C12—H12	118.3 (3)
C11—C1—C2	119.8 (2)	C12—C13—C14	123.7 (3)
C11—C1—C5	123.3 (2)	C12—C13—H13	118.3 (3)
C2—C1—C5	116.8 (2)	C14—C13—H13	118.0 (3)
O1—C2—C1	111.5 (2)	C13—C14—H14B	109.6 (3)
O1—C2—H2B	109.9 (2)	C13—C14—H14C	109.6 (3)
O1—C2—H2A	110.0 (2)	C13—C14—H14A	108.9 (3)
C1—C2—H2B	108.7 (2)	H14B—C14—H14C	110.6 (3)
C1—C2—H2A	108.5 (2)	H14B—C14—H14A	108.8 (3)
H2B—C2—H2A	108.2 (2)	H14C—C14—H14A	109.2 (3)
O1—C3—C4	121.8 (2)	O5—C15—C8	120.2 (3)
O1—C3—C12	115.4 (3)	O5—C15—C16	123.6 (3)
C4—C3—C12	122.8 (3)	C8—C15—C16	116.2 (3)
C3—C4—C5	119.8 (3)	C15—C16—C17	114.5 (3)
C3—C4—H4	120.0 (3)	C15—C16—H16B	108.7 (3)
C5—C4—H4	120.1 (2)	C15—C16—H16A	108.2 (3)
C1—C5—C6	122.7 (2)	C17—C16—H16B	108.8 (3)
C1—C5—C4	117.6 (2)	C17—C16—H16A	108.2 (4)
C6—C5—C4	119.7 (2)	H16B—C16—H16A	108.1 (3)
C7—C6—C5	108.6 (2)	C18—C17—C16	117.6 (4)
C7—C6—H6B	110.3 (2)	C18—C17—H17A	107.5 (4)
C7—C6—H6A	109.9 (2)	C18—C17—H17B	108.2 (4)
C5—C6—H6B	109.8 (2)	C16—C17—H17A	107.6 (4)
C5—C6—H6A	109.7 (2)	C16—C17—H17B	107.9 (4)
H6B—C6—H6A	108.5 (2)	H17A—C17—H17B	107.7 (4)
C10—C7—C8	101.8 (2)	C17—C18—C19	118.3 (4)
C10—C7—C6	110.6 (2)	C17—C18—H18A	108.5 (4)
C10—C7—H7	107.0 (2)	C17—C18—H18B	107.5 (4)
C8—C7—C6	123.1 (2)	C19—C18—H18A	107.5 (4)
C8—C7—H7	106.8 (2)	C19—C18—H18B	107.0 (4)
C6—C7—H7	106.6 (2)	H18A—C18—H18B	107.6 (3)
C9—C8—C15	109.9 (2)	C18—C19—C20	117.4 (5)
C9—C8—C7	100.9 (2)	C18—C19—H19B	107.3 (4)
C9—C8—H8	110.2 (2)	C18—C19—H19A	107.2 (4)
C15—C8—C7	115.3 (2)	C20—C19—H19B	109.1 (5)
C15—C8—H8	109.8 (2)	C20—C19—H19A	109.1 (5)
C7—C8—H8	110.5 (2)	H19B—C19—H19A	106.3 (5)
O2—C9—O3	121.5 (3)	C19—C20—H20A	108.0 (5)
O2—C9—C8	109.9 (2)	C19—C20—H20C	107.7 (5)
O3—C9—C8	128.5 (3)	C19—C20—H20B	108.1 (5)
O2—C10—C11	112.7 (2)	H20A—C20—H20C	110.6 (5)
O2—C10—C7	102.9 (2)	H20A—C20—H20B	111.4 (5)
O2—C10—C21	107.1 (2)	H20C—C20—H20B	110.9 (6)
C11—C10—C7	107.9 (2)	C10—C21—H21B	109.6 (2)
C11—C10—C21	109.4 (2)	C10—C21—H21C	109.7 (2)
C7—C10—C21	116.7 (2)	C10—C21—H21A	109.4 (2)
O4—C11—C10	124.4 (2)	H21B—C21—H21C	109.6 (2)
O4—C11—C1	123.4 (2)	H21B—C21—H21A	109.2 (2)
C10—C11—C1	112.1 (2)	H21C—C21—H21A	109.4 (2)
C3—C12—C13	123.5 (3)
O1—C3—C4—C5	7.3 (4)	H6A—C6—C7—H7	54.91
O1—C3—C4—H4	−173.03	H6B—C6—C7—C10	−69.60
O1—C3—C12—C13	9.6 (5)	H6B—C6—C7—C8	50.84
O1—C3—C12—H12	−170.21	H6B—C6—C7—H7	174.46
O1—C2—C1—C11	−140.5 (4)	C7—C10—O2—C9	−28.6 (4)
O1—C2—C1—C5	38.8 (4)	C7—C10—C21—H21B	−67.40
O2—C9—C8—C15	140.9 (4)	C7—C10—C21—H21C	172.31
O2—C9—C8—C7	18.7 (4)	C7—C10—C21—H21A	52.34
O2—C9—C8—H8	−98.02	C7—C8—C15—C16	−164.8 (5)
O2—C10—C11—O4	−24.6 (4)	H7—C7—C10—C11	46.75
O2—C10—C11—C1	159.0 (4)	H7—C7—C10—C21	170.36
O2—C10—C7—C8	39.2 (4)	H7—C7—C8—C9	77.51
O2—C10—C7—C6	171.6 (4)	H7—C7—C8—C15	−40.78
O2—C10—C7—H7	−72.65	H7—C7—C8—H8	−165.97
O2—C10—C21—H21B	177.95	C8—C9—O2—C10	6.2 (4)
O2—C10—C21—H21C	57.65	C8—C15—C16—C17	−166.7 (5)
O2—C10—C21—H21A	−62.32	C8—C15—C16—H16B	−44.77
O3—C9—O2—C10	−176.4 (4)	C8—C15—C16—H16A	72.47
O3—C9—C8—C15	−36.2 (4)	C8—C7—C10—C11	158.6 (4)
O3—C9—C8—C7	−158.4 (4)	C8—C7—C10—C21	−77.8 (4)
O3—C9—C8—H8	84.82	H8—C8—C15—C16	−39.21
O4—C11—C10—C7	−137.6 (4)	H8—C8—C7—C10	82.04
O4—C11—C10—C21	94.5 (4)	C9—O2—C10—C11	−144.6 (4)
O4—C11—C1—C2	−7.6 (4)	C9—O2—C10—C21	95.0 (4)
O4—C11—C1—C5	173.2 (4)	C9—C8—C15—C16	82.1 (5)
O5—C15—C8—C9	−97.0 (4)	C9—C8—C7—C10	−34.5 (4)
O5—C15—C8—C7	16.2 (4)	C10—C7—C8—C15	−152.8 (4)
O5—C15—C8—H8	141.71	C11—C10—C21—H21B	55.43
O5—C15—C16—C17	12.3 (5)	C11—C10—C21—H21C	−64.87
O5—C15—C16—H16B	134.27	C11—C10—C21—H21A	175.17
O5—C15—C16—H16A	−108.49	C12—C13—C14—H14B	−115.20
C1—C11—C10—C7	46.0 (4)	C12—C13—C14—H14C	123.20
C1—C11—C10—C21	−81.9 (4)	C12—C13—C14—H14A	3.74
C1—C2—O1—C3	−46.8 (5)	H12—C12—C13—C14	−3.21
C1—C5—C6—C7	−13.6 (4)	H12—C12—C13—H13	177.40
C1—C5—C6—H6B	107.01	H13—C13—C14—H14B	64.19
C1—C5—C6—H6A	−133.84	H13—C13—C14—H14C	−57.40
C1—C5—C4—C3	−15.4 (4)	H13—C13—C14—H14A	−176.87
C1—C5—C4—H4	165.00	C15—C16—C17—C18	151.7 (6)
C2—O1—C3—C4	25.2 (4)	C15—C16—C17—H17A	−86.82
C2—O1—C3—C12	−158.3 (4)	C15—C16—C17—H17B	29.11
C2—C1—C11—C10	168.9 (5)	C16—C17—C18—C19	176.9 (7)
C2—C1—C5—C6	173.8 (5)	C16—C17—C18—H18A	54.22
C2—C1—C5—C4	−8.7 (5)	C16—C17—C18—H18B	−61.89
H2A—C2—O1—C3	−167.22	H16A—C16—C17—C18	−87.45
H2A—C2—C1—C11	−19.25	H16A—C16—C17—H17A	33.99
H2A—C2—C1—C5	160.02	H16A—C16—C17—H17B	149.92
H2B—C2—O1—C3	73.79	H16B—C16—C17—C18	29.85
H2B—C2—C1—C11	98.21	H16B—C16—C17—H17A	151.29
H2B—C2—C1—C5	−82.52	H16B—C16—C17—H17B	−92.78
C3—C4—C5—C6	162.2 (4)	C17—C18—C19—C20	176.4 (8)
C3—C12—C13—C14	177.0 (5)	C17—C18—C19—H19B	53.34
C3—C12—C13—H13	−2.39	C17—C18—C19—H19A	−60.52
C4—C3—C12—C13	−174.0 (5)	H17A—C17—C18—C19	55.39
C4—C3—C12—H12	6.19	H17A—C17—C18—H18A	−67.29
C4—C5—C1—C11	170.6 (5)	H17A—C17—C18—H18B	176.61
C4—C5—C6—C7	168.9 (4)	H17B—C17—C18—C19	−60.66
C4—C5—C6—H6B	−70.46	H17B—C17—C18—H18A	176.66
C4—C5—C6—H6A	48.69	H17B—C17—C18—H18B	60.55
H4—C4—C3—C12	10.79	C18—C19—C20—H20A	−170.91
H4—C4—C5—C6	−17.40	C18—C19—C20—H20C	−51.37
C5—C1—C11—C10	−10.3 (4)	C18—C19—C20—H20B	68.45
C5—C6—C7—C10	50.8 (4)	H18A—C18—C19—C20	−60.38
C5—C6—C7—C8	171.2 (5)	H18A—C18—C19—H19B	176.53
C5—C6—C7—H7	−65.17	H18A—C18—C19—H19A	62.67
C5—C4—C3—C12	−168.8 (5)	H18B—C18—C19—C20	54.99
C6—C7—C10—C11	−69.0 (4)	H18B—C18—C19—H19B	−68.10
C6—C7—C10—C21	54.6 (4)	H18B—C18—C19—H19A	178.04
C6—C7—C8—C9	−159.0 (4)	H19A—C19—C20—H20A	66.99
C6—C7—C8—C15	82.8 (5)	H19A—C19—C20—H20C	−173.47
C6—C7—C8—H8	−42.43	H19A—C19—C20—H20B	−53.65
C6—C5—C1—C11	−6.9 (5)	H19B—C19—C20—H20A	−48.72
H6A—C6—C7—C10	170.85	H19B—C19—C20—H20C	70.81
H6A—C6—C7—C8	−68.70	H19B—C19—C20—H20B	−169.36

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O3^i	1.09	2.53	3.281 (4)	125
C16—H16B···O3	1.09	2.57	3.228 (5)	118
C21—H21A···O2^ii	1.10	2.62	3.262 (4)	117
C6—H6A···O4^iii	1.09	2.47	3.529 (3)	163
C6—H6B···O5^iv	1.09	2.59	3.512 (4)	141
C8—H8···O5^iv	1.10	2.54	3.522 (4)	148

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