1-Methyl-spiro­[2.3′]­ox­indole-spiro­[3.2′′]5′′,6′′-di­hydroimidazo[2′′,1′′-b]­thia­zol-3′′-one-4-(2-benzo­[1,3]­dioxol-5-yl)pyrrolidine

The title compound, C₂₃H₂₀N₄O₄S, was synthesized by the intermolecular [3 + 2] cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 2-benzo­[1,3]­dioxol-5-yl­methyl­ene-5,6-di­hydro-imidazo­[2,1-b]­thia­zol-3-one. In the mol­ecule, two spiro junctions link a planar 2-ox­indole ring, a pyrrolidine ring in an envelope conformation and a 5,6-di­hydro-imidazo­[2,1-b]thia­zol-3-one ring. Two mol­ecules are connected into a dimer by two N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.034
• wR factor = 0.107
• Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.73 Ratio
PLAT241_ALERT_2_C Check High   U(eq) as Compared to Neighbors ....         C4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

1-Methyl-spiro[2.3']oxindole-spiro[3.2"]5",6"-dihydro-imidazo [2",1"-b]thiazol-3"-one -4-(2-benzo[1,3]dioxol-5-yl)-pyrrolidine

Crystal data

C23H20N4O4S	Z = 2
Mr = 448.49	F(000) = 468
Triclinic, P1	Dx = 1.397 Mg m^−3
Hall symbol: -P 1	Melting point = 543–544 K
a = 8.741 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.255 (4) Å	Cell parameters from 1010 reflections
c = 14.097 (7) Å	θ = 2.5–26.5°
α = 85.690 (7)°	µ = 0.19 mm^−1
β = 72.206 (7)°	T = 293 K
γ = 79.169 (8)°	Block, colorless
V = 1066.4 (9) Å^3	0.28 × 0.22 × 0.20 mm

Data collection

CCD area detector diffractometer	4388 independent reflections
Radiation source: fine-focus sealed tube	3798 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
φ and ω scans	θmax = 26.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS Bruker, 1997)	h = −10→10
Tmin = 0.863, Tmax = 0.960	k = −11→11
14787 measured reflections	l = −17→17

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.034	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.29 e Å^−3
4388 reflections	Δρmin = −0.21 e Å^−3
290 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.32348 (5)	0.52740 (4)	0.21667 (3)	0.03640 (12)
N1	0.43770 (16)	0.25981 (13)	0.25712 (9)	0.0367 (3)
N2	0.3203 (2)	0.27016 (15)	0.13435 (11)	0.0513 (4)
N3	0.69036 (15)	0.59321 (14)	0.30717 (9)	0.0357 (3)
N4	0.69629 (18)	0.59354 (15)	0.05818 (9)	0.0442 (3)
H4	0.6966	0.6359	0.0017	0.053*
O1	0.54625 (14)	0.27798 (12)	0.38221 (8)	0.0394 (3)
O2	0.53801 (16)	0.78017 (12)	0.16051 (9)	0.0490 (3)
O3	−0.05404 (17)	0.97182 (14)	0.35571 (11)	0.0602 (4)
O4	−0.22692 (16)	0.90232 (16)	0.50477 (12)	0.0680 (4)
C1	0.46612 (17)	0.49963 (14)	0.29192 (10)	0.0283 (3)
C2	0.48738 (17)	0.33329 (15)	0.31813 (10)	0.0302 (3)
C3	0.35882 (18)	0.34049 (16)	0.19407 (10)	0.0339 (3)
C4	0.3765 (4)	0.1123 (2)	0.15350 (18)	0.0774 (7)
H4A	0.4551	0.0680	0.0938	0.093*
H4B	0.2849	0.0602	0.1731	0.093*
C5	0.4559 (3)	0.10349 (17)	0.23800 (14)	0.0527 (5)
H5A	0.3982	0.0512	0.2962	0.063*
H5B	0.5698	0.0571	0.2164	0.063*
C6	0.41472 (17)	0.59236 (15)	0.38852 (10)	0.0312 (3)
H6	0.4268	0.5225	0.4426	0.037*
C7	0.54808 (19)	0.68544 (17)	0.37120 (11)	0.0370 (3)
H7A	0.5210	0.7784	0.3384	0.044*
H7B	0.5658	0.7045	0.4334	0.044*
C8	0.63814 (17)	0.53925 (15)	0.23012 (10)	0.0307 (3)
C9	0.61488 (19)	0.65574 (16)	0.14701 (11)	0.0356 (3)
C10	0.7801 (2)	0.45195 (18)	0.06871 (11)	0.0400 (3)
C11	0.8772 (3)	0.3571 (2)	−0.00492 (14)	0.0598 (5)
H11	0.8893	0.3808	−0.0718	0.072*
C12	0.9564 (3)	0.2254 (2)	0.02362 (16)	0.0675 (6)
H12	1.0220	0.1590	−0.0249	0.081*
C13	0.9401 (2)	0.1904 (2)	0.12233 (16)	0.0602 (5)
H13	0.9958	0.1015	0.1397	0.072*
C14	0.8415 (2)	0.28645 (19)	0.19607 (13)	0.0461 (4)
H14	0.8320	0.2636	0.2628	0.055*
C15	0.75789 (18)	0.41621 (16)	0.16905 (11)	0.0342 (3)
C16	0.24205 (18)	0.67487 (15)	0.42160 (11)	0.0328 (3)
C17	0.1869 (2)	0.79171 (16)	0.36411 (11)	0.0377 (3)
H17	0.2555	0.8216	0.3043	0.045*
C18	0.0281 (2)	0.85975 (16)	0.39987 (12)	0.0402 (4)
C19	−0.0743 (2)	0.81805 (18)	0.48832 (14)	0.0446 (4)
C20	−0.0238 (2)	0.7064 (2)	0.54605 (14)	0.0510 (4)
H20	−0.0935	0.6791	0.6063	0.061*
C21	0.1377 (2)	0.63450 (18)	0.51080 (12)	0.0415 (4)
H21	0.1761	0.5574	0.5484	0.050*
C22	−0.2136 (3)	1.0048 (2)	0.42374 (17)	0.0625 (5)
H22A	−0.2329	1.1040	0.4478	0.075*
H22B	−0.2944	0.9985	0.3906	0.075*
C23	0.8363 (2)	0.6593 (2)	0.27220 (14)	0.0552 (5)
H23A	0.9244	0.5899	0.2327	0.083*
H23B	0.8647	0.6861	0.3283	0.083*
H23C	0.8163	0.7455	0.2325	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0434 (2)	0.02935 (19)	0.0429 (2)	−0.00033 (14)	−0.02566 (17)	−0.00157 (14)
N1	0.0499 (8)	0.0256 (6)	0.0383 (7)	−0.0048 (5)	−0.0199 (6)	0.0010 (5)
N2	0.0831 (11)	0.0375 (7)	0.0468 (8)	−0.0158 (7)	−0.0363 (8)	0.0016 (6)
N3	0.0366 (7)	0.0453 (7)	0.0287 (6)	−0.0104 (5)	−0.0118 (5)	−0.0049 (5)
N4	0.0609 (9)	0.0450 (7)	0.0254 (6)	−0.0082 (6)	−0.0127 (6)	0.0036 (5)
O1	0.0478 (6)	0.0364 (5)	0.0348 (5)	0.0003 (4)	−0.0190 (5)	0.0047 (4)
O2	0.0722 (8)	0.0302 (6)	0.0443 (6)	−0.0048 (5)	−0.0204 (6)	0.0032 (5)
O3	0.0650 (8)	0.0454 (7)	0.0684 (9)	0.0130 (6)	−0.0313 (7)	0.0016 (6)
O4	0.0430 (7)	0.0629 (9)	0.0875 (10)	0.0112 (6)	−0.0152 (7)	−0.0050 (8)
C1	0.0326 (7)	0.0273 (6)	0.0266 (6)	−0.0016 (5)	−0.0133 (5)	−0.0002 (5)
C2	0.0313 (7)	0.0295 (7)	0.0275 (7)	−0.0017 (5)	−0.0078 (5)	0.0001 (5)
C3	0.0412 (8)	0.0326 (7)	0.0303 (7)	−0.0084 (6)	−0.0137 (6)	0.0022 (5)
C4	0.139 (2)	0.0374 (10)	0.0813 (15)	−0.0134 (12)	−0.0709 (16)	−0.0025 (10)
C5	0.0837 (13)	0.0279 (8)	0.0545 (10)	−0.0077 (8)	−0.0333 (10)	−0.0010 (7)
C6	0.0372 (7)	0.0305 (7)	0.0263 (6)	−0.0017 (6)	−0.0119 (6)	−0.0020 (5)
C7	0.0448 (8)	0.0383 (8)	0.0302 (7)	−0.0079 (6)	−0.0131 (6)	−0.0065 (6)
C8	0.0365 (7)	0.0311 (7)	0.0260 (6)	−0.0060 (6)	−0.0116 (6)	0.0001 (5)
C9	0.0458 (8)	0.0346 (7)	0.0302 (7)	−0.0120 (6)	−0.0146 (6)	0.0025 (6)
C10	0.0435 (9)	0.0451 (9)	0.0310 (7)	−0.0088 (7)	−0.0091 (6)	−0.0038 (6)
C11	0.0672 (12)	0.0692 (13)	0.0349 (9)	−0.0031 (10)	−0.0053 (8)	−0.0141 (8)
C12	0.0617 (12)	0.0663 (13)	0.0597 (12)	0.0089 (10)	−0.0023 (10)	−0.0261 (10)
C13	0.0488 (10)	0.0537 (11)	0.0663 (12)	0.0097 (8)	−0.0093 (9)	−0.0076 (9)
C14	0.0384 (8)	0.0494 (9)	0.0455 (9)	0.0020 (7)	−0.0113 (7)	0.0003 (7)
C15	0.0331 (7)	0.0386 (8)	0.0303 (7)	−0.0058 (6)	−0.0081 (6)	−0.0033 (6)
C16	0.0394 (8)	0.0274 (6)	0.0322 (7)	−0.0025 (6)	−0.0126 (6)	−0.0045 (5)
C17	0.0473 (9)	0.0314 (7)	0.0341 (7)	−0.0028 (6)	−0.0137 (6)	−0.0025 (6)
C18	0.0506 (9)	0.0288 (7)	0.0453 (9)	0.0005 (6)	−0.0236 (7)	−0.0051 (6)
C19	0.0381 (8)	0.0391 (8)	0.0564 (10)	0.0014 (6)	−0.0163 (7)	−0.0108 (7)
C20	0.0436 (9)	0.0508 (10)	0.0479 (10)	−0.0042 (7)	−0.0014 (8)	0.0030 (8)
C21	0.0441 (9)	0.0375 (8)	0.0383 (8)	−0.0021 (6)	−0.0095 (7)	0.0032 (6)
C22	0.0593 (12)	0.0473 (10)	0.0856 (15)	0.0147 (9)	−0.0394 (11)	−0.0167 (10)
C23	0.0503 (10)	0.0756 (13)	0.0464 (10)	−0.0293 (9)	−0.0109 (8)	−0.0098 (9)

Geometric parameters (Å, º)

S1—C3	1.7353 (17)	C6—H6	0.9800
S1—C1	1.8421 (15)	C7—H7A	0.9700
N1—C2	1.3483 (19)	C7—H7B	0.9700
N1—C3	1.3800 (19)	C8—C15	1.511 (2)
N1—C5	1.462 (2)	C8—C9	1.565 (2)
N2—C3	1.258 (2)	C10—C11	1.374 (2)
N2—C4	1.483 (2)	C10—C15	1.391 (2)
N3—C8	1.4518 (18)	C11—C12	1.381 (3)
N3—C23	1.452 (2)	C11—H11	0.9300
N3—C7	1.456 (2)	C12—C13	1.375 (3)
N4—C9	1.347 (2)	C12—H12	0.9300
N4—C10	1.397 (2)	C13—C14	1.385 (3)
N4—H4	0.8600	C13—H13	0.9300
O1—C2	1.2077 (17)	C14—C15	1.376 (2)
O2—C9	1.2157 (19)	C14—H14	0.9300
O3—C18	1.3695 (19)	C16—C21	1.382 (2)
O3—C22	1.423 (3)	C16—C17	1.403 (2)
O4—C19	1.374 (2)	C17—C18	1.367 (2)
O4—C22	1.420 (3)	C17—H17	0.9300
C1—C2	1.5460 (19)	C18—C19	1.371 (3)
C1—C6	1.5651 (19)	C19—C20	1.359 (2)
C1—C8	1.585 (2)	C20—C21	1.396 (2)
C4—C5	1.542 (3)	C20—H20	0.9300
C4—H4A	0.9700	C21—H21	0.9300
C4—H4B	0.9700	C22—H22A	0.9700
C5—H5A	0.9700	C22—H22B	0.9700
C5—H5B	0.9700	C23—H23A	0.9600
C6—C16	1.506 (2)	C23—H23B	0.9600
C6—C7	1.527 (2)	C23—H23C	0.9600
C3—S1—C1	91.46 (6)	C15—C8—C1	115.56 (12)
C2—N1—C3	118.21 (12)	C9—C8—C1	109.15 (11)
C2—N1—C5	133.04 (13)	O2—C9—N4	126.35 (14)
C3—N1—C5	108.67 (12)	O2—C9—C8	125.98 (13)
C3—N2—C4	106.04 (14)	N4—C9—C8	107.67 (13)
C8—N3—C23	115.59 (12)	C11—C10—C15	121.64 (16)
C8—N3—C7	106.84 (12)	C11—C10—N4	128.20 (16)
C23—N3—C7	115.15 (14)	C15—C10—N4	110.12 (13)
C9—N4—C10	111.97 (12)	C10—C11—C12	117.82 (18)
C9—N4—H4	124.0	C10—C11—H11	121.1
C10—N4—H4	124.0	C12—C11—H11	121.1
C18—O3—C22	105.59 (15)	C13—C12—C11	121.31 (18)
C19—O4—C22	105.53 (15)	C13—C12—H12	119.3
C2—C1—C6	110.54 (11)	C11—C12—H12	119.3
C2—C1—C8	109.00 (11)	C12—C13—C14	120.48 (18)
C6—C1—C8	104.21 (11)	C12—C13—H13	119.8
C2—C1—S1	104.66 (9)	C14—C13—H13	119.8
C6—C1—S1	116.84 (9)	C15—C14—C13	118.94 (17)
C8—C1—S1	111.52 (9)	C15—C14—H14	120.5
O1—C2—N1	125.45 (13)	C13—C14—H14	120.5
O1—C2—C1	123.90 (13)	C14—C15—C10	119.73 (14)
N1—C2—C1	110.59 (11)	C14—C15—C8	131.85 (14)
N2—C3—N1	117.30 (14)	C10—C15—C8	108.42 (13)
N2—C3—S1	131.27 (12)	C21—C16—C17	120.01 (14)
N1—C3—S1	111.38 (11)	C21—C16—C6	118.77 (13)
N2—C4—C5	107.50 (14)	C17—C16—C6	121.22 (13)
N2—C4—H4A	110.2	C18—C17—C16	117.11 (15)
C5—C4—H4A	110.2	C18—C17—H17	121.4
N2—C4—H4B	110.2	C16—C17—H17	121.4
C5—C4—H4B	110.2	C17—C18—O3	127.66 (16)
H4A—C4—H4B	108.5	C17—C18—C19	122.26 (15)
N1—C5—C4	100.48 (13)	O3—C18—C19	110.06 (15)
N1—C5—H5A	111.7	C20—C19—C18	121.90 (15)
C4—C5—H5A	111.7	C20—C19—O4	128.15 (17)
N1—C5—H5B	111.7	C18—C19—O4	109.94 (15)
C4—C5—H5B	111.7	C19—C20—C21	116.93 (16)
H5A—C5—H5B	109.4	C19—C20—H20	121.5
C16—C6—C7	115.70 (12)	C21—C20—H20	121.5
C16—C6—C1	117.18 (11)	C16—C21—C20	121.79 (15)
C7—C6—C1	104.28 (11)	C16—C21—H21	119.1
C16—C6—H6	106.3	C20—C21—H21	119.1
C7—C6—H6	106.3	O4—C22—O3	108.68 (14)
C1—C6—H6	106.3	O4—C22—H22A	110.0
N3—C7—C6	102.78 (12)	O3—C22—H22A	110.0
N3—C7—H7A	111.2	O4—C22—H22B	110.0
C6—C7—H7A	111.2	O3—C22—H22B	110.0
N3—C7—H7B	111.2	H22A—C22—H22B	108.3
C6—C7—H7B	111.2	N3—C23—H23A	109.5
H7A—C7—H7B	109.1	N3—C23—H23B	109.5
N3—C8—C15	114.90 (12)	H23A—C23—H23B	109.5
N3—C8—C9	114.45 (12)	N3—C23—H23C	109.5
C15—C8—C9	101.40 (11)	H23A—C23—H23C	109.5
N3—C8—C1	101.79 (11)	H23B—C23—H23C	109.5
C3—S1—C1—C2	−17.39 (10)	C10—N4—C9—O2	176.40 (16)
C3—S1—C1—C6	−139.99 (11)	C10—N4—C9—C8	−3.15 (18)
C3—S1—C1—C8	100.32 (10)	N3—C8—C9—O2	−49.5 (2)
C3—N1—C2—O1	173.98 (14)	C15—C8—C9—O2	−173.78 (15)
C5—N1—C2—O1	−9.5 (3)	C1—C8—C9—O2	63.82 (19)
C3—N1—C2—C1	−8.61 (18)	N3—C8—C9—N4	130.07 (14)
C5—N1—C2—C1	167.92 (17)	C15—C8—C9—N4	5.77 (15)
C6—C1—C2—O1	−38.38 (19)	C1—C8—C9—N4	−116.63 (13)
C8—C1—C2—O1	75.58 (17)	C9—N4—C10—C11	−178.91 (18)
S1—C1—C2—O1	−165.00 (12)	C9—N4—C10—C15	−1.17 (19)
C6—C1—C2—N1	144.16 (12)	C15—C10—C11—C12	−1.6 (3)
C8—C1—C2—N1	−101.87 (13)	N4—C10—C11—C12	175.92 (19)
S1—C1—C2—N1	17.55 (13)	C10—C11—C12—C13	−0.6 (3)
C4—N2—C3—N1	0.2 (2)	C11—C12—C13—C14	0.8 (4)
C4—N2—C3—S1	−176.92 (17)	C12—C13—C14—C15	1.1 (3)
C2—N1—C3—N2	176.68 (15)	C13—C14—C15—C10	−3.3 (3)
C5—N1—C3—N2	−0.7 (2)	C13—C14—C15—C8	177.42 (17)
C2—N1—C3—S1	−5.67 (18)	C11—C10—C15—C14	3.6 (3)
C5—N1—C3—S1	177.00 (12)	N4—C10—C15—C14	−174.35 (14)
C1—S1—C3—N2	−168.72 (17)	C11—C10—C15—C8	−176.97 (16)
C1—S1—C3—N1	14.05 (12)	N4—C10—C15—C8	5.12 (18)
C3—N2—C4—C5	0.3 (3)	N3—C8—C15—C14	49.0 (2)
C2—N1—C5—C4	−176.03 (19)	C9—C8—C15—C14	172.94 (16)
C3—N1—C5—C4	0.7 (2)	C1—C8—C15—C14	−69.2 (2)
N2—C4—C5—N1	−0.7 (2)	N3—C8—C15—C10	−130.43 (14)
C2—C1—C6—C16	−108.77 (13)	C9—C8—C15—C10	−6.44 (15)
C8—C1—C6—C16	134.26 (12)	C1—C8—C15—C10	111.42 (14)
S1—C1—C6—C16	10.74 (16)	C7—C6—C16—C21	−121.73 (15)
C2—C1—C6—C7	121.91 (12)	C1—C6—C16—C21	114.58 (15)
C8—C1—C6—C7	4.94 (13)	C7—C6—C16—C17	57.66 (18)
S1—C1—C6—C7	−118.58 (11)	C1—C6—C16—C17	−66.03 (18)
C8—N3—C7—C6	46.05 (14)	C21—C16—C17—C18	−0.9 (2)
C23—N3—C7—C6	175.89 (13)	C6—C16—C17—C18	179.75 (13)
C16—C6—C7—N3	−159.62 (12)	C16—C17—C18—O3	−177.54 (15)
C1—C6—C7—N3	−29.42 (13)	C16—C17—C18—C19	0.6 (2)
C23—N3—C8—C15	62.85 (18)	C22—O3—C18—C17	−178.79 (17)
C7—N3—C8—C15	−167.57 (12)	C22—O3—C18—C19	2.92 (19)
C23—N3—C8—C9	−53.92 (18)	C17—C18—C19—C20	0.2 (3)
C7—N3—C8—C9	75.67 (15)	O3—C18—C19—C20	178.56 (17)
C23—N3—C8—C1	−171.50 (14)	C17—C18—C19—O4	−178.60 (15)
C7—N3—C8—C1	−41.91 (14)	O3—C18—C19—O4	−0.2 (2)
C2—C1—C8—N3	−96.81 (12)	C22—O4—C19—C20	178.72 (19)
C6—C1—C8—N3	21.21 (13)	C22—O4—C19—C18	−2.6 (2)
S1—C1—C8—N3	148.12 (9)	C18—C19—C20—C21	−0.6 (3)
C2—C1—C8—C15	28.40 (15)	O4—C19—C20—C21	177.95 (17)
C6—C1—C8—C15	146.43 (11)	C17—C16—C21—C20	0.5 (2)
S1—C1—C8—C15	−86.66 (12)	C6—C16—C21—C20	179.89 (15)
C2—C1—C8—C9	141.85 (11)	C19—C20—C21—C16	0.2 (3)
C6—C1—C8—C9	−100.12 (12)	C19—O4—C22—O3	4.4 (2)
S1—C1—C8—C9	26.79 (13)	C18—O3—C22—O4	−4.5 (2)