Two stereoisomeric pentacyclic oxin­dole alkaloids from Uncaria tomentosa: uncarine C and uncarine E

The chloro­form solvate of uncarine C (pteropodine), (1′S,3R,4′aS,5′aS,10′aS)-1,2,5′,5′a,7′,8′,10′,10′a-octa­hydro-1′-methyl-2-oxospiro­[3H-indole-3,6′(4′aH)-[1H]­pyrano­[3,4-f]indolizine]-4′-carboxyl­ic acid methyl ester, C₂₁H₂₄N₂O₄·CHCl₃, has an absolute configuration with the spiro C atom in the R configuration. Its epimer at the spiro C atom, uncarine E (isopteropodine), (1′S,3S,4′aS,5′aS,10′aS)-1,2,5′,5′a,7′,8′,10′,10′a-octahydro-1′-methyl-2-oxospiro[3H-indole-3,6′(4′aH)-[1H]pyrano[3,4-f]indolizine]-4′-carboxylic acid methyl ester, C₂₁H₂₄N₂O₄, has Z′ = 3, with no solvent. Both form intermolecular hydrogen bonds involving only the ox­indole, with N...O distances in the range 2.759 (4)–2.894 (5) Å.

Computing details

Data collection: COLLECT (Nonius, 1999) for (I). Cell refinement: DENZO and Scalepak for (I); HKL SCALEPACK (Otwinowski & Minor, 1997) for (II). Data reduction: DENZO and Scalepak (Otwinowski & Minor, 1997) for (I); HKL DENZO and SCALEPACK (Otwinowski & Minor, 1997) for (II). For both compounds, program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

(I) (1'S,3R,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8',10',10'a-octahydro-1'- methyl-2-oxo-spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f]indolizine]-4'-carboxylic acid methyl ester, chloroform solvate

Crystal data

C21H24N2O4·CHCl3	F(000) = 508
Mr = 487.79	Dx = 1.373 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.3190 (5) Å	Cell parameters from 5602 reflections
b = 7.7083 (7) Å	θ = 2.5–32.0°
c = 16.8160 (14) Å	µ = 0.42 mm^−1
β = 102.422 (4)°	T = 120 K
V = 1179.63 (16) Å^3	Needle fragment, colorless
Z = 2	0.32 × 0.12 × 0.08 mm

Data collection

KappaCCD (with Oxford Cryostream) diffractometer	5101 independent reflections
Radiation source: fine-focus sealed tube	3176 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scans with κ offsets	θmax = 32.0°, θmin = 2.7°
Absorption correction: multi-scan (HKL Scalepack; Otwinowski & Minor, 1997)	h = −13→13
Tmin = 0.88, Tmax = 0.97	k = −11→11
5602 measured reflections	l = −24→25

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0998P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max < 0.001
5101 reflections	Δρmax = 1.16 e Å^−3
296 parameters	Δρmin = −0.65 e Å^−3
1 restraint	Absolute structure: 740 Friedel pairs (Flack, 1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (9)

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	Occ. (<1)
Cl1	0.26597 (12)	0.71119 (18)	0.81031 (6)	0.0586 (3)
Cl2	0.33839 (16)	0.6657 (5)	0.98325 (9)	0.1295 (12)
Cl3	0.2804 (2)	1.0009 (3)	0.91474 (17)	0.1112 (12)	0.808 (5)
Cl3A	0.3465 (8)	0.471 (2)	0.9202 (8)	0.133 (6)	0.192 (5)
O1	0.5371 (2)	0.3817 (3)	0.53112 (14)	0.0316 (5)
O2	0.9536 (2)	0.2756 (4)	0.78596 (16)	0.0363 (6)
O3	0.6795 (2)	0.7135 (3)	0.88630 (16)	0.0375 (6)
O4	0.9254 (2)	0.7009 (4)	0.91649 (16)	0.0387 (6)
N1	0.3517 (3)	0.5782 (4)	0.51841 (17)	0.0285 (6)
H1	0.3784	0.6463	0.4822	0.034*
N2	0.4971 (3)	0.1412 (3)	0.68519 (16)	0.0250 (5)
C2	0.4241 (3)	0.4336 (4)	0.54841 (19)	0.0248 (6)
C3	0.4388 (3)	0.3164 (4)	0.69250 (19)	0.0229 (6)
H3	0.3748	0.3117	0.7332	0.027*
C5	0.3695 (4)	0.0399 (4)	0.6464 (2)	0.0318 (7)
H5A	0.3067	0.0128	0.6854	0.038*
H5B	0.3994	−0.0698	0.6240	0.038*
C6	0.2903 (3)	0.1582 (4)	0.5790 (2)	0.0274 (6)
H6A	0.1826	0.1452	0.5715	0.033*
H6B	0.3188	0.1308	0.5270	0.033*
C7	0.3390 (3)	0.3469 (4)	0.6075 (2)	0.0241 (6)
C8	0.2158 (3)	0.4741 (4)	0.60547 (18)	0.0247 (6)
C9	0.1011 (3)	0.4739 (5)	0.6468 (2)	0.0289 (7)
H9	0.0920	0.3838	0.6840	0.035*
C10	0.0003 (3)	0.6101 (5)	0.6321 (2)	0.0339 (8)
H10	−0.0790	0.6120	0.6594	0.041*
C11	0.0133 (4)	0.7424 (5)	0.5784 (2)	0.0342 (8)
H11	−0.0568	0.8338	0.5697	0.041*
C12	0.1271 (4)	0.7436 (5)	0.5372 (2)	0.0343 (8)
H12	0.1364	0.8337	0.5001	0.041*
C13	0.2268 (3)	0.6078 (4)	0.55232 (19)	0.0267 (7)
C14	0.5626 (3)	0.4445 (4)	0.72333 (19)	0.0246 (6)
H14A	0.5209	0.5588	0.7328	0.030*
H14B	0.6227	0.4593	0.6819	0.030*
C15	0.6600 (3)	0.3771 (4)	0.80332 (19)	0.0247 (6)
H15	0.6008	0.3824	0.8463	0.030*
C16	0.7988 (3)	0.4827 (5)	0.83303 (19)	0.0270 (6)
C17	0.9287 (4)	0.4235 (5)	0.8235 (2)	0.0315 (7)
H17	1.0122	0.4928	0.8453	0.038*
C18	0.8783 (4)	−0.0020 (6)	0.7328 (3)	0.0453 (9)
H18A	0.9582	0.0045	0.7034	0.068*
H18B	0.7975	−0.0712	0.7012	0.068*
H18C	0.9143	−0.0565	0.7860	0.068*
C19	0.8232 (3)	0.1808 (5)	0.7449 (2)	0.0318 (7)
H19	0.7830	0.2349	0.6906	0.038*
C20	0.7074 (3)	0.1876 (4)	0.79660 (19)	0.0268 (6)
H20	0.7537	0.1457	0.8525	0.032*
C21	0.5735 (3)	0.0743 (4)	0.7637 (2)	0.0308 (7)
H21A	0.6050	−0.0467	0.7577	0.037*
H21B	0.5069	0.0750	0.8023	0.037*
C22	0.7925 (3)	0.6420 (5)	0.87954 (19)	0.0290 (7)
C23	0.9286 (4)	0.8482 (5)	0.9697 (2)	0.0440 (10)
H23A	0.8845	0.9487	0.9378	0.066*
H23B	1.0307	0.8748	0.9959	0.066*
H23C	0.8730	0.8214	1.0114	0.066*
C24	0.3546 (6)	0.7966 (10)	0.9032 (4)	0.0485 (14)	0.808 (5)
H24	0.4613	0.8106	0.9031	0.058*	0.808 (5)
C24A	0.368 (3)	0.686 (4)	0.9064 (17)	0.050 (6)*	0.192 (5)
H24A	0.4729	0.7166	0.9096	0.060*	0.192 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0614 (6)	0.0729 (8)	0.0417 (6)	−0.0212 (6)	0.0116 (5)	−0.0068 (6)
Cl2	0.0770 (9)	0.254 (4)	0.0579 (8)	−0.0058 (14)	0.0141 (7)	0.0474 (16)
Cl3	0.1007 (14)	0.0782 (14)	0.184 (3)	−0.0315 (11)	0.0951 (16)	−0.0691 (16)
Cl3A	0.046 (4)	0.167 (12)	0.185 (12)	0.012 (5)	0.023 (5)	0.111 (11)
O1	0.0395 (12)	0.0262 (12)	0.0316 (13)	−0.0002 (10)	0.0130 (10)	−0.0017 (11)
O2	0.0310 (11)	0.0350 (13)	0.0451 (15)	0.0011 (10)	0.0133 (10)	−0.0075 (13)
O3	0.0355 (12)	0.0324 (13)	0.0435 (14)	0.0060 (11)	0.0063 (10)	−0.0056 (13)
O4	0.0337 (11)	0.0357 (14)	0.0427 (14)	−0.0017 (11)	−0.0004 (10)	−0.0109 (13)
N1	0.0388 (13)	0.0201 (12)	0.0277 (14)	−0.0031 (11)	0.0094 (11)	0.0039 (12)
N2	0.0309 (12)	0.0161 (11)	0.0271 (14)	−0.0006 (10)	0.0042 (10)	0.0033 (11)
C2	0.0324 (15)	0.0199 (13)	0.0222 (15)	−0.0042 (12)	0.0056 (12)	−0.0015 (13)
C3	0.0305 (14)	0.0169 (13)	0.0220 (15)	−0.0007 (12)	0.0071 (12)	0.0013 (12)
C5	0.0374 (16)	0.0201 (15)	0.0348 (18)	−0.0040 (13)	0.0009 (14)	0.0031 (14)
C6	0.0330 (14)	0.0208 (14)	0.0265 (16)	−0.0014 (12)	0.0023 (12)	−0.0047 (14)
C7	0.0283 (14)	0.0210 (14)	0.0225 (15)	0.0022 (12)	0.0042 (12)	−0.0008 (13)
C8	0.0259 (13)	0.0221 (14)	0.0238 (15)	0.0035 (12)	0.0007 (11)	−0.0009 (14)
C9	0.0309 (14)	0.0265 (15)	0.0268 (16)	−0.0010 (13)	0.0009 (12)	−0.0032 (15)
C10	0.0284 (14)	0.039 (2)	0.0310 (17)	0.0109 (14)	−0.0013 (13)	−0.0084 (16)
C11	0.0338 (16)	0.0282 (16)	0.0354 (18)	0.0081 (14)	−0.0042 (14)	−0.0067 (16)
C12	0.0406 (17)	0.0237 (15)	0.0320 (18)	0.0014 (14)	−0.0065 (14)	0.0014 (15)
C13	0.0322 (15)	0.0200 (14)	0.0245 (16)	−0.0026 (12)	−0.0015 (12)	−0.0028 (13)
C14	0.0287 (14)	0.0193 (14)	0.0259 (15)	0.0005 (12)	0.0056 (12)	0.0018 (13)
C15	0.0266 (14)	0.0252 (14)	0.0223 (15)	0.0014 (12)	0.0051 (11)	0.0023 (14)
C16	0.0252 (13)	0.0299 (16)	0.0253 (15)	0.0009 (13)	0.0040 (11)	0.0010 (15)
C17	0.0314 (15)	0.0324 (17)	0.0311 (18)	−0.0005 (14)	0.0077 (13)	−0.0029 (16)
C18	0.0441 (19)	0.0338 (18)	0.060 (3)	0.0051 (17)	0.0157 (18)	−0.008 (2)
C19	0.0345 (16)	0.0277 (16)	0.0340 (18)	0.0028 (14)	0.0095 (13)	−0.0036 (15)
C20	0.0286 (14)	0.0240 (14)	0.0267 (16)	0.0045 (12)	0.0039 (12)	0.0033 (14)
C21	0.0362 (16)	0.0230 (14)	0.0320 (17)	−0.0020 (13)	0.0045 (14)	0.0069 (15)
C22	0.0317 (15)	0.0277 (15)	0.0249 (15)	−0.0011 (14)	0.0002 (12)	0.0014 (15)
C23	0.051 (2)	0.038 (2)	0.038 (2)	−0.0014 (17)	−0.0029 (17)	−0.0082 (19)
C24	0.042 (3)	0.065 (4)	0.043 (3)	−0.015 (3)	0.017 (2)	−0.015 (3)

Geometric parameters (Å, º)

Cl1—C24A	1.70 (3)	C9—H9	0.9500
Cl1—C24	1.733 (6)	C10—C11	1.384 (5)
Cl2—C24A	1.39 (3)	C10—H10	0.9500
Cl2—C24	1.715 (7)	C11—C12	1.386 (5)
Cl3—C24	1.748 (8)	C11—H11	0.9500
Cl3A—C24A	1.69 (3)	C12—C13	1.386 (5)
O1—C2	1.218 (4)	C12—H12	0.9500
O2—C17	1.347 (4)	C14—C15	1.542 (4)
O2—C19	1.458 (4)	C14—H14A	0.9900
O3—C22	1.215 (4)	C14—H14B	0.9900
O4—C22	1.340 (4)	C15—C16	1.519 (4)
O4—C23	1.442 (5)	C15—C20	1.537 (5)
N1—C2	1.344 (4)	C15—H15	1.0000
N1—C13	1.420 (4)	C16—C17	1.336 (4)
N1—H1	0.8800	C16—C22	1.464 (5)
N2—C21	1.454 (4)	C17—H17	0.9500
N2—C5	1.454 (4)	C18—C19	1.528 (5)
N2—C3	1.470 (4)	C18—H18A	0.9800
C2—C7	1.549 (5)	C18—H18B	0.9800
C3—C14	1.523 (4)	C18—H18C	0.9800
C3—C7	1.547 (4)	C19—C20	1.526 (4)
C3—H3	1.0000	C19—H19	1.0000
C5—C6	1.517 (5)	C20—C21	1.525 (5)
C5—H5A	0.9900	C20—H20	1.0000
C5—H5B	0.9900	C21—H21A	0.9900
C6—C7	1.568 (4)	C21—H21B	0.9900
C6—H6A	0.9900	C23—H23A	0.9800
C6—H6B	0.9900	C23—H23B	0.9800
C7—C8	1.504 (4)	C23—H23C	0.9800
C8—C13	1.382 (5)	C24—H24	1.0000
C8—C9	1.395 (4)	C24A—H24A	1.0000
C9—C10	1.395 (5)
C17—O2—C19	115.9 (2)	H14A—C14—H14B	108.2
C22—O4—C23	116.7 (3)	C16—C15—C20	107.2 (2)
C2—N1—C13	111.8 (3)	C16—C15—C14	114.0 (3)
C2—N1—H1	124.1	C20—C15—C14	112.3 (3)
C13—N1—H1	124.1	C16—C15—H15	107.7
C21—N2—C5	114.2 (3)	C20—C15—H15	107.7
C21—N2—C3	111.6 (3)	C14—C15—H15	107.7
C5—N2—C3	104.4 (2)	C17—C16—C22	119.5 (3)
O1—C2—N1	125.0 (3)	C17—C16—C15	120.5 (3)
O1—C2—C7	126.8 (3)	C22—C16—C15	119.7 (3)
N1—C2—C7	108.2 (3)	C16—C17—O2	126.7 (3)
N2—C3—C14	110.9 (2)	C16—C17—H17	116.7
N2—C3—C7	102.8 (2)	O2—C17—H17	116.7
C14—C3—C7	118.5 (3)	C19—C18—H18A	109.5
N2—C3—H3	108.0	C19—C18—H18B	109.5
C14—C3—H3	108.0	H18A—C18—H18B	109.5
C7—C3—H3	108.0	C19—C18—H18C	109.5
N2—C5—C6	103.4 (3)	H18A—C18—H18C	109.5
N2—C5—H5A	111.1	H18B—C18—H18C	109.5
C6—C5—H5A	111.1	O2—C19—C20	109.4 (3)
N2—C5—H5B	111.1	O2—C19—C18	104.8 (3)
C6—C5—H5B	111.1	C20—C19—C18	114.0 (3)
H5A—C5—H5B	109.1	O2—C19—H19	109.5
C5—C6—C7	105.5 (2)	C20—C19—H19	109.5
C5—C6—H6A	110.6	C18—C19—H19	109.5
C7—C6—H6A	110.6	C21—C20—C19	113.4 (3)
C5—C6—H6B	110.6	C21—C20—C15	110.2 (2)
C7—C6—H6B	110.6	C19—C20—C15	108.9 (3)
H6A—C6—H6B	108.8	C21—C20—H20	108.1
C8—C7—C3	115.1 (3)	C19—C20—H20	108.1
C8—C7—C2	101.4 (3)	C15—C20—H20	108.1
C3—C7—C2	111.7 (2)	N2—C21—C20	109.2 (3)
C8—C7—C6	115.4 (3)	N2—C21—H21A	109.8
C3—C7—C6	102.6 (2)	C20—C21—H21A	109.8
C2—C7—C6	111.0 (3)	N2—C21—H21B	109.8
C13—C8—C9	119.6 (3)	C20—C21—H21B	109.8
C13—C8—C7	109.8 (3)	H21A—C21—H21B	108.3
C9—C8—C7	130.6 (3)	O3—C22—O4	122.4 (3)
C10—C9—C8	118.0 (3)	O3—C22—C16	124.5 (3)
C10—C9—H9	121.0	O4—C22—C16	113.1 (3)
C8—C9—H9	121.0	O4—C23—H23A	109.5
C11—C10—C9	121.4 (3)	O4—C23—H23B	109.5
C11—C10—H10	119.3	H23A—C23—H23B	109.5
C9—C10—H10	119.3	O4—C23—H23C	109.5
C10—C11—C12	121.0 (3)	H23A—C23—H23C	109.5
C10—C11—H11	119.5	H23B—C23—H23C	109.5
C12—C11—H11	119.5	Cl2—C24—Cl1	112.2 (4)
C13—C12—C11	117.2 (3)	Cl2—C24—Cl3	109.9 (3)
C13—C12—H12	121.4	Cl1—C24—Cl3	108.6 (4)
C11—C12—H12	121.4	Cl2—C24—H24	108.7
C8—C13—C12	122.8 (3)	Cl1—C24—H24	108.7
C8—C13—N1	108.7 (3)	Cl3—C24—H24	108.7
C12—C13—N1	128.5 (3)	Cl2—C24A—Cl3A	73.0 (15)
C3—C14—C15	109.9 (3)	Cl2—C24A—Cl1	136.0 (17)
C3—C14—H14A	109.7	Cl3A—C24A—Cl1	100.7 (16)
C15—C14—H14A	109.7	Cl2—C24A—H24A	111.3
C3—C14—H14B	109.7	Cl3A—C24A—H24A	111.3
C15—C14—H14B	109.7	Cl1—C24A—H24A	111.3
C13—N1—C2—O1	−177.8 (3)	C9—C8—C13—N1	179.9 (3)
C13—N1—C2—C7	2.3 (3)	C7—C8—C13—N1	−0.3 (3)
C21—N2—C3—C14	62.7 (3)	C11—C12—C13—C8	0.4 (5)
C5—N2—C3—C14	−173.4 (3)	C11—C12—C13—N1	179.9 (3)
C21—N2—C3—C7	−169.6 (2)	C2—N1—C13—C8	−1.4 (3)
C5—N2—C3—C7	−45.8 (3)	C2—N1—C13—C12	179.1 (3)
C21—N2—C5—C6	166.2 (3)	N2—C3—C14—C15	−54.0 (3)
C3—N2—C5—C6	44.1 (3)	C7—C3—C14—C15	−172.6 (3)
N2—C5—C6—C7	−24.6 (3)	C3—C14—C15—C16	172.0 (3)
N2—C3—C7—C8	154.4 (3)	C3—C14—C15—C20	49.8 (3)
C14—C3—C7—C8	−82.9 (3)	C20—C15—C16—C17	21.6 (4)
N2—C3—C7—C2	−90.7 (3)	C14—C15—C16—C17	−103.4 (4)
C14—C3—C7—C2	32.0 (4)	C20—C15—C16—C22	−152.4 (3)
N2—C3—C7—C6	28.3 (3)	C14—C15—C16—C22	82.6 (4)
C14—C3—C7—C6	151.0 (3)	C22—C16—C17—O2	176.6 (3)
O1—C2—C7—C8	177.9 (3)	C15—C16—C17—O2	2.6 (6)
N1—C2—C7—C8	−2.3 (3)	C19—O2—C17—C16	6.6 (5)
O1—C2—C7—C3	54.8 (4)	C17—O2—C19—C20	−39.5 (4)
N1—C2—C7—C3	−125.4 (3)	C17—O2—C19—C18	−162.1 (3)
O1—C2—C7—C6	−59.0 (4)	O2—C19—C20—C21	−173.2 (3)
N1—C2—C7—C6	120.8 (3)	C18—C19—C20—C21	−56.3 (4)
C5—C6—C7—C8	−128.3 (3)	O2—C19—C20—C15	63.7 (3)
C5—C6—C7—C3	−2.4 (3)	C18—C19—C20—C15	−179.4 (3)
C5—C6—C7—C2	117.0 (3)	C16—C15—C20—C21	−177.8 (3)
C3—C7—C8—C13	122.2 (3)	C14—C15—C20—C21	−51.8 (3)
C2—C7—C8—C13	1.5 (3)	C16—C15—C20—C19	−52.8 (3)
C6—C7—C8—C13	−118.6 (3)	C14—C15—C20—C19	73.2 (3)
C3—C7—C8—C9	−57.9 (4)	C5—N2—C21—C20	178.1 (3)
C2—C7—C8—C9	−178.7 (3)	C3—N2—C21—C20	−63.7 (3)
C6—C7—C8—C9	61.3 (4)	C19—C20—C21—N2	−64.9 (3)
C13—C8—C9—C10	0.5 (4)	C15—C20—C21—N2	57.5 (3)
C7—C8—C9—C10	−179.3 (3)	C23—O4—C22—O3	4.0 (5)
C8—C9—C10—C11	−0.4 (5)	C23—O4—C22—C16	−174.5 (3)
C9—C10—C11—C12	0.3 (5)	C17—C16—C22—O3	174.0 (4)
C10—C11—C12—C13	−0.3 (5)	C15—C16—C22—O3	−12.0 (5)
C9—C8—C13—C12	−0.6 (4)	C17—C16—C22—O4	−7.6 (5)
C7—C8—C13—C12	179.3 (3)	C15—C16—C22—O4	166.4 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^i	0.88	2.01	2.759 (4)	142
C9—H9···O2^ii	0.95	2.50	3.330 (4)	146
C24—H24···O3	1.00	2.24	3.167 (6)	153

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

(II) (1'S,3S,4'aS,5'aS,10'aS)-1,2,5',5'a,7',8', 10',10'a-octahydro -1'-methyl-2-oxo-spiro[3H-indole-3,6'(4'aH)-[1H]pyrano[3,4-f] indolizine]-4'-carboxylic acid methyl ester

Crystal data

C21H24N2O4	The unit-cell dimensions at 296K were measured on an Enraf-Nonius CAD4 diffractometer using CuKα radiation (λ=1.54184 Å), using 25 reflections in the theta range 15.6-19.6°.
Mr = 368.42	Dx = 1.298 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9943 (8) Å	Cell parameters from 6595 reflections
b = 21.062 (3) Å	θ = 2.5–25.0°
c = 12.3039 (15) Å	µ = 0.09 mm^−1
β = 96.860 (6)°	T = 120 K
V = 2828.7 (5) Å^3	Needle, colorless
Z = 6	0.58 × 0.07 × 0.05 mm
F(000) = 1176

Data collection

KappaCCD (with Oxford Cryostream) diffractometer	4478 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
Graphite monochromator	θmax = 25.1°, θmin = 2.5°
ω scans with κ offsets	h = −13→13
8293 measured reflections	k = −23→25
8293 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.108	H-atom parameters constrained
S = 0.89	w = 1/[σ^2(Fo^2) + (0.0282P)^2] where P = (Fo^2 + 2Fc^2)/3
8293 reflections	(Δ/σ)max = 0.001
736 parameters	Δρmax = 0.21 e Å^−3
1 restraint	Δρmin = −0.25 e Å^−3

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
O1A	0.9823 (3)	0.24244 (16)	0.4239 (3)	0.0312 (9)
O2A	0.5102 (3)	0.40584 (16)	0.7357 (3)	0.0351 (9)
O3A	0.6383 (3)	0.44231 (17)	0.3848 (3)	0.0330 (9)
O4A	0.5253 (3)	0.51349 (15)	0.4653 (3)	0.0325 (9)
N1A	1.1035 (3)	0.30046 (19)	0.5535 (3)	0.0289 (11)
H1NA	1.1601	0.3126	0.5130	0.035*
N2A	0.7344 (3)	0.23825 (18)	0.6632 (3)	0.0246 (10)
C2A	1.0062 (4)	0.2633 (2)	0.5175 (5)	0.0261 (13)
C3A	0.7953 (4)	0.2729 (2)	0.5821 (4)	0.0222 (12)
H3A	0.7658	0.2555	0.5080	0.027*
C5A	0.7790 (4)	0.1731 (2)	0.6534 (4)	0.0324 (13)
H5A1	0.7341	0.1514	0.5894	0.039*
H5A2	0.7697	0.1483	0.7203	0.039*
C6A	0.9155 (4)	0.1816 (2)	0.6385 (4)	0.0283 (13)
H6A1	0.9374	0.1547	0.5777	0.034*
H6A2	0.9684	0.1698	0.7063	0.034*
C7A	0.9309 (4)	0.2528 (2)	0.6121 (4)	0.0235 (12)
C8A	1.0015 (4)	0.2898 (2)	0.7027 (4)	0.0255 (13)
C9A	0.9833 (4)	0.2982 (3)	0.8110 (4)	0.0344 (14)
H9A	0.9140	0.2804	0.8391	0.041*
C10A	1.0702 (5)	0.3338 (3)	0.8784 (5)	0.0423 (15)
H10A	1.0603	0.3398	0.9534	0.051*
C11A	1.1700 (5)	0.3602 (3)	0.8367 (5)	0.0380 (15)
H11A	1.2268	0.3846	0.8837	0.046*
C12A	1.1899 (4)	0.3521 (2)	0.7277 (4)	0.0310 (13)
H12A	1.2591	0.3695	0.6991	0.037*
C13A	1.1020 (4)	0.3171 (2)	0.6641 (4)	0.0269 (13)
C14A	0.7642 (4)	0.3432 (2)	0.5827 (4)	0.0248 (12)
H14A	0.8059	0.3658	0.5271	0.030*
H14B	0.7919	0.3617	0.6554	0.030*
C15A	0.6228 (4)	0.3502 (2)	0.5561 (4)	0.0237 (12)
H15A	0.5986	0.3331	0.4808	0.028*
C16A	0.5796 (4)	0.4179 (2)	0.5587 (4)	0.0222 (12)
C17A	0.5246 (4)	0.4387 (3)	0.6425 (4)	0.0309 (13)
H17A	0.4921	0.4805	0.6369	0.037*
C18A	0.5073 (4)	0.3097 (3)	0.8343 (4)	0.0376 (14)
H18A	0.5031	0.3385	0.8964	0.056*
H18B	0.5545	0.2718	0.8591	0.056*
H18C	0.4243	0.2972	0.8040	0.056*
C19A	0.5695 (4)	0.3433 (2)	0.7467 (4)	0.0297 (13)
H19A	0.6583	0.3490	0.7736	0.036*
C20A	0.5577 (4)	0.3109 (2)	0.6362 (4)	0.0224 (12)
H20A	0.4686	0.3106	0.6077	0.027*
C21A	0.6009 (4)	0.2425 (2)	0.6384 (4)	0.0268 (13)
H21A	0.5619	0.2188	0.6946	0.032*
H21B	0.5752	0.2225	0.5665	0.032*
C22A	0.5871 (4)	0.4571 (2)	0.4614 (5)	0.0274 (13)
C23A	0.5237 (4)	0.5518 (2)	0.3683 (4)	0.0346 (14)
H23A	0.6073	0.5561	0.3490	0.052*
H23B	0.4909	0.5939	0.3819	0.052*
H23C	0.4719	0.5315	0.3078	0.052*
O1B	0.6194 (3)	0.29109 (16)	0.2775 (3)	0.0310 (9)
O2B	0.1452 (3)	0.03740 (17)	0.3765 (3)	0.0396 (10)
O3B	0.3279 (3)	0.20947 (17)	0.5859 (3)	0.0351 (9)
O4B	0.2100 (3)	0.13731 (16)	0.6582 (3)	0.0352 (9)
N1B	0.7486 (3)	0.20499 (19)	0.3081 (3)	0.0274 (10)
H1NB	0.8133	0.2252	0.3401	0.033*
N2B	0.3560 (3)	0.1505 (2)	0.1553 (3)	0.0306 (11)
C2B	0.6403 (4)	0.2338 (3)	0.2699 (4)	0.0279 (13)
C3B	0.4278 (4)	0.1855 (2)	0.2464 (4)	0.0273 (13)
H3B	0.3997	0.2307	0.2440	0.033*
C5B	0.3952 (4)	0.1781 (3)	0.0558 (4)	0.0427 (15)
H5B1	0.3434	0.2151	0.0312	0.051*
H5B2	0.3895	0.1463	−0.0039	0.051*
C6B	0.5286 (4)	0.1987 (3)	0.0873 (4)	0.0315 (13)
H6B1	0.5385	0.2446	0.0739	0.038*
H6B2	0.5842	0.1747	0.0447	0.038*
C7B	0.5563 (4)	0.1833 (2)	0.2118 (4)	0.0240 (12)
C8B	0.6292 (4)	0.1231 (2)	0.2350 (4)	0.0230 (12)
C9B	0.6040 (4)	0.0615 (2)	0.2078 (4)	0.0280 (13)
H9B	0.5269	0.0500	0.1696	0.034*
C10B	0.6934 (4)	0.0156 (2)	0.2369 (4)	0.0317 (13)
H10B	0.6764	−0.0277	0.2191	0.038*
C11B	0.8061 (5)	0.0321 (2)	0.2913 (4)	0.0328 (14)
H11B	0.8658	0.0001	0.3099	0.039*
C12B	0.8337 (4)	0.0952 (2)	0.3195 (4)	0.0307 (14)
H12B	0.9109	0.1070	0.3573	0.037*
C13B	0.7437 (4)	0.1395 (2)	0.2899 (4)	0.0248 (12)
C14B	0.4041 (4)	0.1573 (2)	0.3546 (4)	0.0272 (12)
H14C	0.4509	0.1810	0.4154	0.033*
H14D	0.4317	0.1125	0.3589	0.033*
C15B	0.2650 (4)	0.1607 (2)	0.3658 (4)	0.0281 (13)
H15B	0.2414	0.2066	0.3674	0.034*
C16B	0.2319 (4)	0.1300 (2)	0.4691 (4)	0.0283 (13)
C17B	0.1742 (4)	0.0741 (3)	0.4652 (4)	0.0325 (14)
H17B	0.1513	0.0585	0.5323	0.039*
C18B	0.1217 (5)	0.0219 (3)	0.1860 (5)	0.0561 (18)
H18D	0.1164	−0.0227	0.2077	0.084*
H18E	0.1621	0.0247	0.1193	0.084*
H18F	0.0391	0.0399	0.1720	0.084*
C19B	0.1942 (4)	0.0582 (2)	0.2758 (4)	0.0346 (14)
H19B	0.2819	0.0448	0.2800	0.041*
C20B	0.1883 (4)	0.1298 (3)	0.2678 (4)	0.0322 (14)
H20B	0.1011	0.1422	0.2717	0.039*
C21B	0.2245 (4)	0.1571 (3)	0.1602 (4)	0.0347 (14)
H21C	0.1790	0.1345	0.0974	0.042*
H21D	0.2016	0.2025	0.1545	0.042*
C22B	0.2621 (4)	0.1639 (3)	0.5727 (4)	0.0289 (13)
C23B	0.2466 (4)	0.1669 (3)	0.7629 (4)	0.0391 (15)
H23D	0.3357	0.1637	0.7807	0.059*
H23E	0.2064	0.1454	0.8196	0.059*
H23F	0.2226	0.2117	0.7596	0.059*
O1C	1.3072 (3)	0.33869 (17)	0.4440 (3)	0.0348 (9)
O2C	0.7472 (3)	0.40391 (17)	0.0221 (3)	0.0347 (9)
O3C	0.9602 (3)	0.21591 (16)	0.1487 (3)	0.0381 (10)
O4C	0.8220 (3)	0.21659 (16)	−0.0024 (3)	0.0370 (9)
N1C	1.4011 (3)	0.36389 (19)	0.2925 (3)	0.0278 (10)
H1NC	1.4620	0.3366	0.3022	0.033*
N2C	1.0237 (3)	0.45901 (18)	0.3033 (3)	0.0270 (10)
C2C	1.3138 (4)	0.3703 (2)	0.3616 (4)	0.0281 (13)
C3C	1.0923 (4)	0.3994 (2)	0.3013 (4)	0.0225 (12)
H3C	1.0780	0.3738	0.3672	0.027*
C5C	1.0820 (4)	0.4919 (3)	0.3996 (4)	0.0358 (14)
H5C1	1.0512	0.4757	0.4667	0.043*
H5C2	1.0662	0.5381	0.3938	0.043*
C6C	1.2186 (4)	0.4779 (2)	0.4015 (4)	0.0312 (14)
H6C1	1.2544	0.4642	0.4755	0.037*
H6C2	1.2629	0.5161	0.3805	0.037*
C7C	1.2264 (4)	0.4238 (2)	0.3170 (4)	0.0238 (12)
C8C	1.2771 (4)	0.4428 (2)	0.2134 (4)	0.0242 (12)
C9C	1.2432 (4)	0.4879 (2)	0.1348 (4)	0.0319 (13)
H9C	1.1734	0.5138	0.1402	0.038*
C10C	1.3102 (4)	0.4956 (3)	0.0483 (5)	0.0367 (14)
H10C	1.2859	0.5263	−0.0066	0.044*
C11C	1.4129 (4)	0.4588 (3)	0.0410 (4)	0.0377 (14)
H11C	1.4586	0.4650	−0.0189	0.045*
C12C	1.4511 (4)	0.4129 (2)	0.1188 (4)	0.0283 (13)
H12C	1.5215	0.3876	0.1134	0.034*
C13C	1.3822 (4)	0.4061 (2)	0.2039 (4)	0.0231 (12)
C14C	1.0493 (4)	0.3612 (2)	0.2003 (4)	0.0266 (13)
H14E	1.0968	0.3213	0.2001	0.032*
H14F	1.0620	0.3856	0.1339	0.032*
C15C	0.9116 (4)	0.3459 (2)	0.1997 (4)	0.0243 (12)
H15C	0.9025	0.3174	0.2634	0.029*
C16C	0.8578 (4)	0.3127 (2)	0.0979 (4)	0.0234 (12)
C17C	0.7784 (4)	0.3419 (3)	0.0219 (4)	0.0323 (13)
H17C	0.7412	0.3167	−0.0369	0.039*
C18C	0.7445 (5)	0.5037 (2)	0.1080 (5)	0.0414 (15)
H18G	0.7127	0.5162	0.0332	0.062*
H18H	0.7975	0.5375	0.1420	0.062*
H18I	0.6760	0.4969	0.1508	0.062*
C19C	0.8171 (4)	0.4433 (2)	0.1050 (4)	0.0320 (13)
H19C	0.8988	0.4532	0.0811	0.038*
C20C	0.8355 (4)	0.4071 (2)	0.2130 (4)	0.0253 (12)
H20C	0.7528	0.3934	0.2298	0.030*
C21C	0.8925 (4)	0.4462 (2)	0.3096 (4)	0.0271 (12)
H21E	0.8481	0.4870	0.3114	0.032*
H21F	0.8837	0.4231	0.3783	0.032*
C22C	0.8863 (4)	0.2453 (2)	0.0870 (4)	0.0279 (13)
C23C	0.8493 (5)	0.1506 (3)	−0.0161 (5)	0.0567 (19)
H23G	0.9328	0.1464	−0.0356	0.085*
H23H	0.7911	0.1326	−0.0746	0.085*
H23I	0.8428	0.1279	0.0524	0.085*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1A	0.0217 (17)	0.039 (2)	0.032 (2)	0.0032 (16)	0.0035 (16)	−0.0040 (19)
O2A	0.039 (2)	0.036 (2)	0.032 (2)	0.0118 (18)	0.0106 (17)	0.0059 (19)
O3A	0.0325 (19)	0.036 (2)	0.032 (2)	0.0016 (17)	0.0105 (18)	0.001 (2)
O4A	0.0322 (19)	0.026 (2)	0.040 (2)	0.0071 (17)	0.0066 (17)	0.0057 (19)
N1A	0.021 (2)	0.032 (3)	0.036 (3)	−0.008 (2)	0.0076 (19)	0.003 (2)
N2A	0.019 (2)	0.027 (3)	0.028 (3)	0.0024 (19)	0.0055 (18)	0.005 (2)
C2A	0.021 (3)	0.026 (3)	0.030 (4)	0.002 (2)	−0.001 (2)	0.003 (3)
C3A	0.018 (2)	0.024 (3)	0.025 (3)	0.002 (2)	0.004 (2)	0.002 (2)
C5A	0.027 (3)	0.026 (3)	0.044 (4)	−0.001 (2)	0.004 (2)	0.000 (3)
C6A	0.024 (2)	0.023 (3)	0.038 (3)	0.007 (2)	0.005 (2)	0.004 (3)
C7A	0.014 (2)	0.027 (3)	0.029 (3)	0.001 (2)	0.002 (2)	−0.002 (3)
C8A	0.022 (3)	0.024 (3)	0.030 (3)	0.001 (2)	0.001 (2)	0.007 (3)
C9A	0.031 (3)	0.043 (4)	0.029 (4)	0.002 (3)	0.003 (2)	0.002 (3)
C10A	0.038 (3)	0.056 (4)	0.032 (4)	−0.005 (3)	0.000 (3)	−0.002 (3)
C11A	0.033 (3)	0.041 (4)	0.039 (4)	−0.010 (3)	−0.001 (3)	−0.008 (3)
C12A	0.029 (3)	0.030 (3)	0.033 (4)	0.003 (2)	0.003 (3)	−0.003 (3)
C13A	0.029 (3)	0.029 (3)	0.023 (3)	−0.001 (2)	0.002 (2)	0.000 (3)
C14A	0.016 (2)	0.028 (3)	0.030 (3)	−0.002 (2)	0.000 (2)	−0.003 (3)
C15A	0.015 (2)	0.032 (3)	0.024 (3)	−0.003 (2)	0.003 (2)	−0.003 (3)
C16A	0.021 (3)	0.023 (3)	0.023 (3)	0.001 (2)	0.003 (2)	−0.004 (3)
C17A	0.028 (3)	0.027 (3)	0.037 (4)	0.005 (2)	0.002 (3)	0.001 (3)
C18A	0.030 (3)	0.055 (4)	0.029 (3)	0.005 (3)	0.005 (2)	0.002 (3)
C19A	0.025 (3)	0.034 (3)	0.031 (3)	0.007 (2)	0.004 (2)	0.006 (3)
C20A	0.011 (2)	0.031 (3)	0.025 (3)	−0.003 (2)	0.001 (2)	−0.002 (3)
C21A	0.014 (2)	0.038 (3)	0.029 (3)	−0.003 (2)	0.006 (2)	0.007 (3)
C22A	0.025 (3)	0.024 (3)	0.031 (4)	−0.003 (2)	−0.004 (3)	−0.006 (3)
C23A	0.034 (3)	0.032 (3)	0.038 (4)	−0.002 (3)	0.001 (3)	0.004 (3)
O1B	0.0295 (19)	0.022 (2)	0.043 (2)	−0.0027 (16)	0.0102 (17)	−0.0004 (18)
O2B	0.035 (2)	0.043 (2)	0.041 (3)	−0.0125 (18)	0.0052 (19)	−0.002 (2)
O3B	0.0296 (19)	0.034 (2)	0.042 (2)	−0.0048 (18)	0.0025 (17)	0.0013 (19)
O4B	0.0371 (19)	0.040 (2)	0.029 (2)	−0.0025 (17)	0.0074 (18)	0.0038 (19)
N1B	0.021 (2)	0.025 (3)	0.037 (3)	−0.0034 (19)	0.0031 (19)	0.000 (2)
N2B	0.018 (2)	0.049 (3)	0.024 (3)	−0.0038 (19)	0.0018 (19)	0.003 (2)
C2B	0.023 (3)	0.034 (4)	0.028 (3)	0.003 (2)	0.008 (2)	0.003 (3)
C3B	0.023 (3)	0.029 (3)	0.030 (3)	0.001 (2)	0.004 (2)	−0.001 (3)
C5B	0.034 (3)	0.064 (4)	0.032 (4)	−0.008 (3)	0.007 (3)	0.008 (3)
C6B	0.022 (3)	0.046 (4)	0.027 (3)	0.002 (2)	0.005 (2)	0.007 (3)
C7B	0.013 (2)	0.029 (3)	0.030 (3)	0.000 (2)	0.001 (2)	0.001 (3)
C8B	0.024 (3)	0.026 (3)	0.020 (3)	−0.004 (2)	0.009 (2)	−0.005 (2)
C9B	0.021 (3)	0.039 (4)	0.024 (3)	−0.005 (3)	0.003 (2)	−0.008 (3)
C10B	0.031 (3)	0.029 (3)	0.037 (4)	0.000 (3)	0.013 (3)	−0.003 (3)
C11B	0.035 (3)	0.032 (4)	0.031 (3)	0.007 (3)	0.004 (3)	0.006 (3)
C12B	0.023 (3)	0.038 (4)	0.031 (3)	−0.001 (3)	−0.002 (2)	0.005 (3)
C13B	0.020 (3)	0.027 (3)	0.027 (3)	−0.002 (2)	0.003 (2)	0.000 (3)
C14B	0.022 (2)	0.032 (3)	0.028 (3)	0.000 (2)	0.004 (2)	−0.001 (3)
C15B	0.021 (2)	0.033 (3)	0.031 (3)	0.003 (2)	0.007 (2)	0.008 (3)
C16B	0.020 (3)	0.030 (3)	0.035 (4)	−0.004 (2)	0.005 (2)	0.008 (3)
C17B	0.031 (3)	0.042 (4)	0.024 (3)	0.005 (3)	0.001 (3)	0.002 (3)
C18B	0.058 (4)	0.068 (5)	0.043 (4)	−0.027 (4)	0.007 (3)	−0.012 (4)
C19B	0.026 (3)	0.042 (4)	0.036 (4)	−0.010 (3)	0.007 (3)	−0.003 (3)
C20B	0.020 (2)	0.044 (4)	0.032 (3)	−0.005 (3)	0.001 (2)	0.003 (3)
C21B	0.016 (2)	0.057 (4)	0.031 (3)	−0.001 (3)	0.001 (2)	0.003 (3)
C22B	0.022 (3)	0.033 (4)	0.032 (4)	0.014 (3)	0.006 (3)	0.009 (3)
C23B	0.044 (3)	0.042 (4)	0.032 (4)	0.009 (3)	0.004 (3)	0.001 (3)
O1C	0.0231 (18)	0.043 (2)	0.039 (2)	−0.0007 (17)	0.0047 (17)	0.011 (2)
O2C	0.0325 (19)	0.036 (2)	0.034 (2)	0.0034 (18)	−0.0028 (17)	−0.0011 (19)
O3C	0.038 (2)	0.030 (2)	0.044 (3)	0.0054 (18)	−0.0041 (18)	−0.0004 (19)
O4C	0.044 (2)	0.030 (2)	0.037 (2)	−0.0094 (18)	0.0024 (18)	−0.0092 (18)
N1C	0.020 (2)	0.028 (3)	0.036 (3)	0.0004 (19)	0.005 (2)	0.007 (2)
N2C	0.023 (2)	0.026 (3)	0.032 (3)	0.0011 (19)	0.0040 (19)	−0.009 (2)
C2C	0.023 (3)	0.034 (3)	0.026 (3)	−0.004 (2)	0.000 (3)	0.006 (3)
C3C	0.025 (3)	0.023 (3)	0.021 (3)	0.003 (2)	0.007 (2)	−0.001 (2)
C5C	0.028 (3)	0.046 (4)	0.035 (3)	−0.004 (3)	0.008 (3)	−0.017 (3)
C6C	0.019 (3)	0.040 (4)	0.036 (4)	0.001 (2)	0.007 (2)	−0.014 (3)
C7C	0.018 (2)	0.026 (3)	0.028 (3)	−0.006 (2)	0.005 (2)	−0.007 (3)
C8C	0.026 (3)	0.018 (3)	0.029 (3)	−0.006 (2)	0.008 (2)	−0.006 (3)
C9C	0.026 (3)	0.026 (3)	0.044 (4)	−0.003 (2)	0.005 (3)	0.002 (3)
C10C	0.034 (3)	0.035 (4)	0.042 (4)	0.007 (3)	0.008 (3)	0.010 (3)
C11C	0.035 (3)	0.047 (4)	0.032 (3)	0.000 (3)	0.010 (3)	−0.003 (3)
C12C	0.030 (3)	0.021 (3)	0.033 (3)	0.005 (2)	0.003 (3)	−0.002 (3)
C13C	0.019 (3)	0.028 (3)	0.023 (3)	−0.005 (2)	0.001 (2)	−0.002 (3)
C14C	0.019 (2)	0.028 (3)	0.032 (3)	−0.004 (2)	0.003 (2)	−0.004 (2)
C15C	0.022 (2)	0.024 (3)	0.027 (3)	0.002 (2)	0.003 (2)	−0.003 (2)
C16C	0.022 (3)	0.022 (3)	0.027 (3)	−0.002 (2)	0.006 (2)	−0.002 (3)
C17C	0.031 (3)	0.035 (3)	0.031 (3)	−0.001 (3)	0.002 (3)	−0.003 (3)
C18C	0.044 (3)	0.026 (3)	0.053 (4)	0.010 (3)	0.001 (3)	0.002 (3)
C19C	0.028 (3)	0.029 (3)	0.039 (4)	−0.006 (3)	0.004 (2)	0.002 (3)
C20C	0.018 (2)	0.031 (3)	0.027 (3)	−0.004 (2)	0.006 (2)	−0.001 (3)
C21C	0.020 (2)	0.032 (3)	0.030 (3)	−0.006 (2)	0.005 (2)	−0.003 (3)
C22C	0.027 (3)	0.031 (3)	0.028 (3)	−0.007 (3)	0.016 (3)	−0.008 (3)
C23C	0.060 (4)	0.031 (4)	0.078 (5)	−0.008 (3)	0.003 (3)	−0.024 (3)

Geometric parameters (Å, º)

O1A—C2A	1.231 (5)	C10B—H10B	0.9500
O2A—C17A	1.365 (6)	C11B—C12B	1.398 (7)
O2A—C19A	1.470 (6)	C11B—H11B	0.9500
O3A—C22A	1.196 (6)	C12B—C13B	1.376 (6)
O4A—C22A	1.372 (6)	C12B—H12B	0.9500
O4A—C23A	1.439 (6)	C14B—C15B	1.554 (6)
N1A—C2A	1.356 (6)	C14B—H14C	0.9900
N1A—C13A	1.407 (6)	C14B—H14D	0.9900
N1A—H1NA	0.8800	C15B—C16B	1.510 (6)
N2A—C3A	1.461 (6)	C15B—C20B	1.531 (6)
N2A—C21A	1.467 (5)	C15B—H15B	1.0000
N2A—C5A	1.466 (6)	C16B—C17B	1.336 (7)
C2A—C7A	1.523 (7)	C16B—C22B	1.463 (7)
C3A—C14A	1.519 (6)	C17B—H17B	0.9500
C3A—C7A	1.552 (6)	C18B—C19B	1.493 (7)
C3A—H3A	1.0000	C18B—H18D	0.9800
C5A—C6A	1.544 (6)	C18B—H18E	0.9800
C5A—H5A1	0.9900	C18B—H18F	0.9800
C5A—H5A2	0.9900	C19B—C20B	1.511 (7)
C6A—C7A	1.548 (6)	C19B—H19B	1.0000
C6A—H6A1	0.9900	C20B—C21B	1.539 (6)
C6A—H6A2	0.9900	C20B—H20B	1.0000
C7A—C8A	1.499 (6)	C21B—H21C	0.9900
C8A—C13A	1.378 (6)	C21B—H21D	0.9900
C8A—C9A	1.382 (6)	C23B—H23D	0.9800
C9A—C10A	1.405 (7)	C23B—H23E	0.9800
C9A—H9A	0.9500	C23B—H23F	0.9800
C10A—C11A	1.382 (7)	O1C—C2C	1.222 (6)
C10A—H10A	0.9500	O2C—C17C	1.349 (6)
C11A—C12A	1.394 (7)	O2C—C19C	1.459 (5)
C11A—H11A	0.9500	O3C—C22C	1.213 (5)
C12A—C13A	1.382 (6)	O4C—C22C	1.374 (5)
C12A—H12A	0.9500	O4C—C23C	1.436 (6)
C14A—C15A	1.557 (5)	N1C—C2C	1.362 (6)
C14A—H14A	0.9900	N1C—C13C	1.402 (6)
C14A—H14B	0.9900	N1C—H1NC	0.8800
C15A—C16A	1.507 (7)	N2C—C5C	1.453 (6)
C15A—C20A	1.528 (6)	N2C—C3C	1.467 (5)
C15A—H15A	1.0000	N2C—C21C	1.479 (5)
C16A—C17A	1.329 (6)	C2C—C7C	1.539 (6)
C16A—C22A	1.464 (7)	C3C—C14C	1.508 (6)
C17A—H17A	0.9500	C3C—C7C	1.552 (6)
C18A—C19A	1.517 (7)	C3C—H3C	1.0000
C18A—H18A	0.9800	C5C—C6C	1.528 (6)
C18A—H18B	0.9800	C5C—H5C1	0.9900
C18A—H18C	0.9800	C5C—H5C2	0.9900
C19A—C20A	1.513 (6)	C6C—C7C	1.553 (6)
C19A—H19A	1.0000	C6C—H6C1	0.9900
C20A—C21A	1.516 (7)	C6C—H6C2	0.9900
C20A—H20A	1.0000	C7C—C8C	1.504 (7)
C21A—H21A	0.9900	C8C—C9C	1.376 (6)
C21A—H21B	0.9900	C8C—C13C	1.407 (6)
C23A—H23A	0.9800	C9C—C10C	1.374 (7)
C23A—H23B	0.9800	C9C—H9C	0.9500
C23A—H23C	0.9800	C10C—C11C	1.381 (7)
O1B—C2B	1.234 (6)	C10C—H10C	0.9500
O2B—C17B	1.344 (6)	C11C—C12C	1.389 (7)
O2B—C19B	1.475 (6)	C11C—H11C	0.9500
O3B—C22B	1.201 (6)	C12C—C13C	1.371 (6)
O4B—C22B	1.376 (6)	C12C—H12C	0.9500
O4B—C23B	1.445 (5)	C14C—C15C	1.547 (6)
N1B—C2B	1.369 (6)	C14C—H14E	0.9900
N1B—C13B	1.398 (6)	C14C—H14F	0.9900
N1B—H1NB	0.8800	C15C—C16C	1.493 (6)
N2B—C21B	1.461 (5)	C15C—C20C	1.556 (6)
N2B—C5B	1.466 (6)	C15C—H15C	1.0000
N2B—C3B	1.487 (6)	C16C—C17C	1.349 (6)
C2B—C7B	1.528 (6)	C16C—C22C	1.463 (7)
C3B—C14B	1.509 (6)	C17C—H17C	0.9500
C3B—C7B	1.524 (6)	C18C—C19C	1.506 (7)
C3B—H3B	1.0000	C18C—H18G	0.9800
C5B—C6B	1.535 (6)	C18C—H18H	0.9800
C5B—H5B1	0.9900	C18C—H18I	0.9800
C5B—H5B2	0.9900	C19C—C20C	1.524 (6)
C6B—C7B	1.559 (6)	C19C—H19C	1.0000
C6B—H6B1	0.9900	C20C—C21C	1.517 (6)
C6B—H6B2	0.9900	C20C—H20C	1.0000
C7B—C8B	1.509 (6)	C21C—H21E	0.9900
C8B—C9B	1.359 (6)	C21C—H21F	0.9900
C8B—C13B	1.399 (6)	C23C—H23G	0.9800
C9B—C10B	1.395 (6)	C23C—H23H	0.9800
C9B—H9B	0.9500	C23C—H23I	0.9800
C10B—C11B	1.381 (7)
C17A—O2A—C19A	115.9 (4)	N1B—C13B—C8B	109.6 (4)
C22A—O4A—C23A	114.4 (4)	C3B—C14B—C15B	109.6 (4)
C2A—N1A—C13A	111.1 (4)	C3B—C14B—H14C	109.8
C2A—N1A—H1NA	124.5	C15B—C14B—H14C	109.8
C13A—N1A—H1NA	124.5	C3B—C14B—H14D	109.8
C3A—N2A—C21A	110.9 (3)	C15B—C14B—H14D	109.8
C3A—N2A—C5A	103.1 (4)	H14C—C14B—H14D	108.2
C21A—N2A—C5A	112.1 (4)	C16B—C15B—C20B	108.3 (4)
O1A—C2A—N1A	125.7 (5)	C16B—C15B—C14B	113.1 (4)
O1A—C2A—C7A	126.0 (4)	C20B—C15B—C14B	111.5 (4)
N1A—C2A—C7A	108.3 (4)	C16B—C15B—H15B	107.9
N2A—C3A—C14A	111.3 (4)	C20B—C15B—H15B	107.9
N2A—C3A—C7A	101.9 (3)	C14B—C15B—H15B	107.9
C14A—C3A—C7A	118.4 (4)	C17B—C16B—C22B	121.3 (5)
N2A—C3A—H3A	108.3	C17B—C16B—C15B	120.6 (5)
C14A—C3A—H3A	108.3	C22B—C16B—C15B	118.1 (5)
C7A—C3A—H3A	108.3	C16B—C17B—O2B	127.0 (5)
N2A—C5A—C6A	103.9 (4)	C16B—C17B—H17B	116.5
N2A—C5A—H5A1	111.0	O2B—C17B—H17B	116.5
C6A—C5A—H5A1	111.0	C19B—C18B—H18D	109.5
N2A—C5A—H5A2	111.0	C19B—C18B—H18E	109.5
C6A—C5A—H5A2	111.0	H18D—C18B—H18E	109.5
H5A1—C5A—H5A2	109.0	C19B—C18B—H18F	109.5
C5A—C6A—C7A	105.6 (4)	H18D—C18B—H18F	109.5
C5A—C6A—H6A1	110.6	H18E—C18B—H18F	109.5
C7A—C6A—H6A1	110.6	O2B—C19B—C18B	104.6 (4)
C5A—C6A—H6A2	110.6	O2B—C19B—C20B	109.5 (4)
C7A—C6A—H6A2	110.6	C18B—C19B—C20B	116.6 (5)
H6A1—C6A—H6A2	108.8	O2B—C19B—H19B	108.6
C8A—C7A—C2A	102.3 (4)	C18B—C19B—H19B	108.6
C8A—C7A—C6A	114.1 (4)	C20B—C19B—H19B	108.6
C2A—C7A—C6A	112.6 (4)	C19B—C20B—C15B	111.0 (4)
C8A—C7A—C3A	115.6 (4)	C19B—C20B—C21B	114.5 (4)
C2A—C7A—C3A	111.9 (4)	C15B—C20B—C21B	110.1 (4)
C6A—C7A—C3A	100.9 (3)	C19B—C20B—H20B	107.0
C13A—C8A—C9A	119.5 (4)	C15B—C20B—H20B	107.0
C13A—C8A—C7A	109.0 (4)	C21B—C20B—H20B	107.0
C9A—C8A—C7A	131.4 (5)	N2B—C21B—C20B	111.0 (4)
C8A—C9A—C10A	118.1 (5)	N2B—C21B—H21C	109.4
C8A—C9A—H9A	121.0	C20B—C21B—H21C	109.4
C10A—C9A—H9A	121.0	N2B—C21B—H21D	109.4
C11A—C10A—C9A	120.6 (5)	C20B—C21B—H21D	109.4
C11A—C10A—H10A	119.7	H21C—C21B—H21D	108.0
C9A—C10A—H10A	119.7	O3B—C22B—O4B	121.4 (5)
C10A—C11A—C12A	122.0 (5)	O3B—C22B—C16B	125.3 (5)
C10A—C11A—H11A	119.0	O4B—C22B—C16B	113.3 (5)
C12A—C11A—H11A	119.0	O4B—C23B—H23D	109.5
C13A—C12A—C11A	115.5 (5)	O4B—C23B—H23E	109.5
C13A—C12A—H12A	122.3	H23D—C23B—H23E	109.5
C11A—C12A—H12A	122.3	O4B—C23B—H23F	109.5
C8A—C13A—C12A	124.2 (5)	H23D—C23B—H23F	109.5
C8A—C13A—N1A	109.4 (4)	H23E—C23B—H23F	109.5
C12A—C13A—N1A	126.3 (5)	C17C—O2C—C19C	116.0 (4)
C3A—C14A—C15A	108.1 (4)	C22C—O4C—C23C	115.2 (4)
C3A—C14A—H14A	110.1	C2C—N1C—C13C	111.9 (4)
C15A—C14A—H14A	110.1	C2C—N1C—H1NC	124.1
C3A—C14A—H14B	110.1	C13C—N1C—H1NC	124.1
C15A—C14A—H14B	110.1	C5C—N2C—C3C	104.2 (3)
H14A—C14A—H14B	108.4	C5C—N2C—C21C	112.5 (4)
C16A—C15A—C20A	109.0 (4)	C3C—N2C—C21C	110.5 (4)
C16A—C15A—C14A	113.3 (4)	O1C—C2C—N1C	125.5 (5)
C20A—C15A—C14A	110.3 (4)	O1C—C2C—C7C	126.7 (5)
C16A—C15A—H15A	108.0	N1C—C2C—C7C	107.8 (4)
C20A—C15A—H15A	108.0	N2C—C3C—C14C	111.1 (4)
C14A—C15A—H15A	108.0	N2C—C3C—C7C	101.3 (4)
C17A—C16A—C22A	121.6 (5)	C14C—C3C—C7C	118.6 (4)
C17A—C16A—C15A	120.1 (5)	N2C—C3C—H3C	108.4
C22A—C16A—C15A	117.9 (4)	C14C—C3C—H3C	108.4
C16A—C17A—O2A	126.4 (5)	C7C—C3C—H3C	108.4
C16A—C17A—H17A	116.8	N2C—C5C—C6C	104.9 (4)
O2A—C17A—H17A	116.8	N2C—C5C—H5C1	110.8
C19A—C18A—H18A	109.5	C6C—C5C—H5C1	110.8
C19A—C18A—H18B	109.5	N2C—C5C—H5C2	110.8
H18A—C18A—H18B	109.5	C6C—C5C—H5C2	110.8
C19A—C18A—H18C	109.5	H5C1—C5C—H5C2	108.8
H18A—C18A—H18C	109.5	C5C—C6C—C7C	105.3 (4)
H18B—C18A—H18C	109.5	C5C—C6C—H6C1	110.7
O2A—C19A—C20A	109.4 (4)	C7C—C6C—H6C1	110.7
O2A—C19A—C18A	104.5 (4)	C5C—C6C—H6C2	110.7
C20A—C19A—C18A	115.5 (4)	C7C—C6C—H6C2	110.7
O2A—C19A—H19A	109.1	H6C1—C6C—H6C2	108.8
C20A—C19A—H19A	109.1	C8C—C7C—C2C	102.6 (4)
C18A—C19A—H19A	109.1	C8C—C7C—C3C	115.2 (4)
C19A—C20A—C21A	114.8 (4)	C2C—C7C—C3C	110.2 (4)
C19A—C20A—C15A	109.8 (4)	C8C—C7C—C6C	115.3 (4)
C21A—C20A—C15A	110.9 (4)	C2C—C7C—C6C	112.4 (4)
C19A—C20A—H20A	107.0	C3C—C7C—C6C	101.4 (4)
C21A—C20A—H20A	107.0	C9C—C8C—C13C	118.5 (5)
C15A—C20A—H20A	107.0	C9C—C8C—C7C	133.1 (5)
N2A—C21A—C20A	111.4 (4)	C13C—C8C—C7C	108.4 (4)
N2A—C21A—H21A	109.4	C10C—C9C—C8C	120.1 (5)
C20A—C21A—H21A	109.4	C10C—C9C—H9C	120.0
N2A—C21A—H21B	109.4	C8C—C9C—H9C	120.0
C20A—C21A—H21B	109.4	C9C—C10C—C11C	120.1 (5)
H21A—C21A—H21B	108.0	C9C—C10C—H10C	119.9
O3A—C22A—O4A	122.3 (5)	C11C—C10C—H10C	119.9
O3A—C22A—C16A	125.1 (5)	C10C—C11C—C12C	121.8 (5)
O4A—C22A—C16A	112.5 (5)	C10C—C11C—H11C	119.1
O4A—C23A—H23A	109.5	C12C—C11C—H11C	119.1
O4A—C23A—H23B	109.5	C13C—C12C—C11C	116.8 (5)
H23A—C23A—H23B	109.5	C13C—C12C—H12C	121.6
O4A—C23A—H23C	109.5	C11C—C12C—H12C	121.6
H23A—C23A—H23C	109.5	C12C—C13C—N1C	128.0 (4)
H23B—C23A—H23C	109.5	C12C—C13C—C8C	122.7 (5)
C17B—O2B—C19B	115.8 (4)	N1C—C13C—C8C	109.3 (4)
C22B—O4B—C23B	114.2 (4)	C3C—C14C—C15C	109.0 (4)
C2B—N1B—C13B	111.6 (4)	C3C—C14C—H14E	109.9
C2B—N1B—H1NB	124.2	C15C—C14C—H14E	109.9
C13B—N1B—H1NB	124.2	C3C—C14C—H14F	109.9
C21B—N2B—C5B	112.8 (4)	C15C—C14C—H14F	109.9
C21B—N2B—C3B	111.2 (4)	H14E—C14C—H14F	108.3
C5B—N2B—C3B	104.4 (4)	C16C—C15C—C14C	113.0 (4)
O1B—C2B—N1B	124.7 (4)	C16C—C15C—C20C	108.2 (4)
O1B—C2B—C7B	127.5 (4)	C14C—C15C—C20C	111.4 (4)
N1B—C2B—C7B	107.7 (4)	C16C—C15C—H15C	108.0
N2B—C3B—C14B	109.7 (4)	C14C—C15C—H15C	108.0
N2B—C3B—C7B	101.7 (4)	C20C—C15C—H15C	108.0
C14B—C3B—C7B	119.9 (4)	C17C—C16C—C22C	120.5 (5)
N2B—C3B—H3B	108.3	C17C—C16C—C15C	121.8 (5)
C14B—C3B—H3B	108.3	C22C—C16C—C15C	117.6 (4)
C7B—C3B—H3B	108.3	C16C—C17C—O2C	125.7 (5)
N2B—C5B—C6B	105.6 (4)	C16C—C17C—H17C	117.2
N2B—C5B—H5B1	110.6	O2C—C17C—H17C	117.2
C6B—C5B—H5B1	110.6	C19C—C18C—H18G	109.5
N2B—C5B—H5B2	110.6	C19C—C18C—H18H	109.5
C6B—C5B—H5B2	110.6	H18G—C18C—H18H	109.5
H5B1—C5B—H5B2	108.8	C19C—C18C—H18I	109.5
C5B—C6B—C7B	105.0 (4)	H18G—C18C—H18I	109.5
C5B—C6B—H6B1	110.8	H18H—C18C—H18I	109.5
C7B—C6B—H6B1	110.8	O2C—C19C—C18C	105.2 (4)
C5B—C6B—H6B2	110.8	O2C—C19C—C20C	109.2 (4)
C7B—C6B—H6B2	110.8	C18C—C19C—C20C	114.6 (4)
H6B1—C6B—H6B2	108.8	O2C—C19C—H19C	109.2
C8B—C7B—C3B	117.4 (4)	C18C—C19C—H19C	109.2
C8B—C7B—C2B	102.7 (3)	C20C—C19C—H19C	109.2
C3B—C7B—C2B	112.2 (4)	C21C—C20C—C19C	114.3 (4)
C8B—C7B—C6B	113.4 (4)	C21C—C20C—C15C	110.8 (4)
C3B—C7B—C6B	100.9 (3)	C19C—C20C—C15C	109.9 (4)
C2B—C7B—C6B	110.5 (4)	C21C—C20C—H20C	107.2
C9B—C8B—C13B	120.0 (4)	C19C—C20C—H20C	107.2
C9B—C8B—C7B	131.9 (4)	C15C—C20C—H20C	107.2
C13B—C8B—C7B	108.1 (4)	N2C—C21C—C20C	111.8 (4)
C8B—C9B—C10B	118.8 (4)	N2C—C21C—H21E	109.2
C8B—C9B—H9B	120.6	C20C—C21C—H21E	109.2
C10B—C9B—H9B	120.6	N2C—C21C—H21F	109.2
C11B—C10B—C9B	120.9 (5)	C20C—C21C—H21F	109.2
C11B—C10B—H10B	119.6	H21E—C21C—H21F	107.9
C9B—C10B—H10B	119.6	O3C—C22C—O4C	121.1 (5)
C10B—C11B—C12B	121.0 (5)	O3C—C22C—C16C	124.9 (5)
C10B—C11B—H11B	119.5	O4C—C22C—C16C	113.9 (4)
C12B—C11B—H11B	119.5	O4C—C23C—H23G	109.5
C13B—C12B—C11B	116.8 (4)	O4C—C23C—H23H	109.5
C13B—C12B—H12B	121.6	H23G—C23C—H23H	109.5
C11B—C12B—H12B	121.6	O4C—C23C—H23I	109.5
C12B—C13B—N1B	127.8 (4)	H23G—C23C—H23I	109.5
C12B—C13B—C8B	122.5 (5)	H23H—C23C—H23I	109.5
C13A—N1A—C2A—O1A	178.7 (5)	C2B—N1B—C13B—C12B	−178.3 (5)
C13A—N1A—C2A—C7A	−0.5 (5)	C2B—N1B—C13B—C8B	1.5 (6)
C21A—N2A—C3A—C14A	62.1 (5)	C9B—C8B—C13B—C12B	−0.7 (8)
C5A—N2A—C3A—C14A	−177.8 (3)	C7B—C8B—C13B—C12B	−177.7 (5)
C21A—N2A—C3A—C7A	−170.8 (4)	C9B—C8B—C13B—N1B	179.5 (4)
C5A—N2A—C3A—C7A	−50.6 (4)	C7B—C8B—C13B—N1B	2.5 (6)
C3A—N2A—C5A—C6A	40.0 (4)	N2B—C3B—C14B—C15B	−58.5 (5)
C21A—N2A—C5A—C6A	159.3 (4)	C7B—C3B—C14B—C15B	−175.4 (4)
N2A—C5A—C6A—C7A	−13.8 (5)	C3B—C14B—C15B—C16B	176.7 (4)
O1A—C2A—C7A—C8A	−178.8 (5)	C3B—C14B—C15B—C20B	54.3 (5)
N1A—C2A—C7A—C8A	0.3 (5)	C20B—C15B—C16B—C17B	17.7 (6)
O1A—C2A—C7A—C6A	58.3 (6)	C14B—C15B—C16B—C17B	−106.4 (5)
N1A—C2A—C7A—C6A	−122.6 (4)	C20B—C15B—C16B—C22B	−160.8 (4)
O1A—C2A—C7A—C3A	−54.5 (6)	C14B—C15B—C16B—C22B	75.1 (6)
N1A—C2A—C7A—C3A	124.6 (4)	C22B—C16B—C17B—O2B	−177.6 (4)
C5A—C6A—C7A—C8A	109.0 (4)	C15B—C16B—C17B—O2B	3.9 (8)
C5A—C6A—C7A—C2A	−135.0 (4)	C19B—O2B—C17B—C16B	7.1 (7)
C5A—C6A—C7A—C3A	−15.6 (5)	C17B—O2B—C19B—C18B	−164.5 (4)
N2A—C3A—C7A—C8A	−83.6 (5)	C17B—O2B—C19B—C20B	−38.8 (5)
C14A—C3A—C7A—C8A	38.8 (6)	O2B—C19B—C20B—C15B	60.7 (5)
N2A—C3A—C7A—C2A	159.8 (4)	C18B—C19B—C20B—C15B	179.2 (4)
C14A—C3A—C7A—C2A	−77.8 (5)	O2B—C19B—C20B—C21B	−174.0 (3)
N2A—C3A—C7A—C6A	39.9 (5)	C18B—C19B—C20B—C21B	−55.5 (6)
C14A—C3A—C7A—C6A	162.3 (4)	C16B—C15B—C20B—C19B	−48.9 (5)
C2A—C7A—C8A—C13A	−0.1 (5)	C14B—C15B—C20B—C19B	76.2 (5)
C6A—C7A—C8A—C13A	121.8 (4)	C16B—C15B—C20B—C21B	−176.8 (4)
C3A—C7A—C8A—C13A	−121.9 (4)	C14B—C15B—C20B—C21B	−51.6 (5)
C2A—C7A—C8A—C9A	−178.1 (5)	C5B—N2B—C21B—C20B	−177.8 (4)
C6A—C7A—C8A—C9A	−56.2 (7)	C3B—N2B—C21B—C20B	−60.9 (5)
C3A—C7A—C8A—C9A	60.0 (7)	C19B—C20B—C21B—N2B	−71.0 (5)
C13A—C8A—C9A—C10A	−1.0 (7)	C15B—C20B—C21B—N2B	54.8 (6)
C7A—C8A—C9A—C10A	176.9 (5)	C23B—O4B—C22B—O3B	−3.0 (6)
C8A—C9A—C10A—C11A	0.8 (8)	C23B—O4B—C22B—C16B	175.2 (4)
C9A—C10A—C11A—C12A	−0.9 (8)	C17B—C16B—C22B—O3B	169.2 (5)
C10A—C11A—C12A—C13A	1.2 (7)	C15B—C16B—C22B—O3B	−12.3 (7)
C9A—C8A—C13A—C12A	1.4 (7)	C17B—C16B—C22B—O4B	−9.0 (6)
C7A—C8A—C13A—C12A	−176.9 (4)	C15B—C16B—C22B—O4B	169.5 (4)
C9A—C8A—C13A—N1A	178.1 (4)	C13C—N1C—C2C—O1C	178.7 (5)
C7A—C8A—C13A—N1A	−0.2 (5)	C13C—N1C—C2C—C7C	−1.3 (5)
C11A—C12A—C13A—C8A	−1.4 (7)	C5C—N2C—C3C—C14C	−175.6 (4)
C11A—C12A—C13A—N1A	−177.6 (5)	C21C—N2C—C3C—C14C	63.3 (5)
C2A—N1A—C13A—C8A	0.4 (6)	C5C—N2C—C3C—C7C	−48.7 (5)
C2A—N1A—C13A—C12A	177.1 (5)	C21C—N2C—C3C—C7C	−169.8 (4)
N2A—C3A—C14A—C15A	−59.5 (5)	C3C—N2C—C5C—C6C	38.4 (5)
C7A—C3A—C14A—C15A	−177.1 (4)	C21C—N2C—C5C—C6C	158.2 (4)
C3A—C14A—C15A—C16A	177.7 (4)	N2C—C5C—C6C—C7C	−12.5 (6)
C3A—C14A—C15A—C20A	55.2 (5)	O1C—C2C—C7C—C8C	−178.0 (5)
C20A—C15A—C16A—C17A	18.2 (6)	N1C—C2C—C7C—C8C	2.0 (5)
C14A—C15A—C16A—C17A	−105.0 (5)	O1C—C2C—C7C—C3C	−54.8 (6)
C20A—C15A—C16A—C22A	−154.8 (4)	N1C—C2C—C7C—C3C	125.1 (4)
C14A—C15A—C16A—C22A	82.0 (5)	O1C—C2C—C7C—C6C	57.5 (6)
C22A—C16A—C17A—O2A	178.6 (4)	N1C—C2C—C7C—C6C	−122.5 (4)
C15A—C16A—C17A—O2A	5.8 (7)	N2C—C3C—C7C—C8C	−86.5 (5)
C19A—O2A—C17A—C16A	4.7 (6)	C14C—C3C—C7C—C8C	35.3 (6)
C17A—O2A—C19A—C20A	−38.2 (5)	N2C—C3C—C7C—C2C	158.1 (4)
C17A—O2A—C19A—C18A	−162.5 (4)	C14C—C3C—C7C—C2C	−80.1 (5)
O2A—C19A—C20A—C21A	−172.6 (4)	N2C—C3C—C7C—C6C	38.8 (5)
C18A—C19A—C20A—C21A	−55.0 (5)	C14C—C3C—C7C—C6C	160.6 (4)
O2A—C19A—C20A—C15A	61.7 (5)	C5C—C6C—C7C—C8C	109.1 (5)
C18A—C19A—C20A—C15A	179.3 (4)	C5C—C6C—C7C—C2C	−133.8 (5)
C16A—C15A—C20A—C19A	−50.7 (5)	C5C—C6C—C7C—C3C	−16.1 (5)
C14A—C15A—C20A—C19A	74.3 (5)	C2C—C7C—C8C—C9C	−179.5 (5)
C16A—C15A—C20A—C21A	−178.6 (4)	C3C—C7C—C8C—C9C	60.8 (7)
C14A—C15A—C20A—C21A	−53.6 (5)	C6C—C7C—C8C—C9C	−56.9 (7)
C3A—N2A—C21A—C20A	−58.8 (5)	C2C—C7C—C8C—C13C	−2.0 (5)
C5A—N2A—C21A—C20A	−173.5 (4)	C3C—C7C—C8C—C13C	−121.7 (4)
C19A—C20A—C21A—N2A	−70.1 (5)	C6C—C7C—C8C—C13C	120.6 (4)
C15A—C20A—C21A—N2A	55.0 (5)	C13C—C8C—C9C—C10C	1.2 (7)
C23A—O4A—C22A—O3A	2.2 (6)	C7C—C8C—C9C—C10C	178.4 (5)
C23A—O4A—C22A—C16A	−176.3 (4)	C8C—C9C—C10C—C11C	−1.0 (8)
C17A—C16A—C22A—O3A	177.5 (5)	C9C—C10C—C11C—C12C	0.6 (8)
C15A—C16A—C22A—O3A	−9.6 (7)	C10C—C11C—C12C—C13C	−0.3 (7)
C17A—C16A—C22A—O4A	−4.0 (6)	C11C—C12C—C13C—N1C	−179.7 (4)
C15A—C16A—C22A—O4A	168.8 (4)	C11C—C12C—C13C—C8C	0.4 (7)
C13B—N1B—C2B—O1B	178.5 (5)	C2C—N1C—C13C—C12C	−179.9 (5)
C13B—N1B—C2B—C7B	−4.8 (5)	C2C—N1C—C13C—C8C	0.0 (5)
C21B—N2B—C3B—C14B	63.1 (5)	C9C—C8C—C13C—C12C	−0.9 (7)
C5B—N2B—C3B—C14B	−174.9 (4)	C7C—C8C—C13C—C12C	−178.8 (4)
C21B—N2B—C3B—C7B	−169.0 (4)	C9C—C8C—C13C—N1C	179.3 (4)
C5B—N2B—C3B—C7B	−47.0 (5)	C7C—C8C—C13C—N1C	1.4 (5)
C21B—N2B—C5B—C6B	151.4 (4)	N2C—C3C—C14C—C15C	−59.9 (5)
C3B—N2B—C5B—C6B	30.5 (5)	C7C—C3C—C14C—C15C	−176.6 (4)
N2B—C5B—C6B—C7B	−2.7 (6)	C3C—C14C—C15C—C16C	175.2 (4)
N2B—C3B—C7B—C8B	−80.4 (5)	C3C—C14C—C15C—C20C	53.2 (5)
C14B—C3B—C7B—C8B	40.6 (6)	C14C—C15C—C16C—C17C	−109.0 (5)
N2B—C3B—C7B—C2B	161.0 (4)	C20C—C15C—C16C—C17C	14.8 (6)
C14B—C3B—C7B—C2B	−77.9 (6)	C14C—C15C—C16C—C22C	75.9 (6)
N2B—C3B—C7B—C6B	43.4 (5)	C20C—C15C—C16C—C22C	−160.3 (4)
C14B—C3B—C7B—C6B	164.4 (4)	C22C—C16C—C17C—O2C	−178.5 (4)
O1B—C2B—C7B—C8B	−177.6 (5)	C15C—C16C—C17C—O2C	6.5 (8)
N1B—C2B—C7B—C8B	5.9 (5)	C19C—O2C—C17C—C16C	7.6 (7)
O1B—C2B—C7B—C3B	−50.6 (7)	C17C—O2C—C19C—C18C	−165.2 (4)
N1B—C2B—C7B—C3B	132.9 (4)	C17C—O2C—C19C—C20C	−41.7 (5)
O1B—C2B—C7B—C6B	61.2 (6)	O2C—C19C—C20C—C21C	−172.4 (4)
N1B—C2B—C7B—C6B	−115.4 (4)	C18C—C19C—C20C—C21C	−54.7 (5)
C5B—C6B—C7B—C8B	101.5 (5)	O2C—C19C—C20C—C15C	62.3 (5)
C5B—C6B—C7B—C3B	−25.0 (5)	C18C—C19C—C20C—C15C	−180.0 (4)
C5B—C6B—C7B—C2B	−143.8 (4)	C16C—C15C—C20C—C21C	−174.9 (4)
C3B—C7B—C8B—C9B	55.0 (7)	C14C—C15C—C20C—C21C	−50.2 (5)
C2B—C7B—C8B—C9B	178.5 (5)	C16C—C15C—C20C—C19C	−47.7 (5)
C6B—C7B—C8B—C9B	−62.2 (7)	C14C—C15C—C20C—C19C	77.1 (5)
C3B—C7B—C8B—C13B	−128.5 (4)	C5C—N2C—C21C—C20C	−175.3 (4)
C2B—C7B—C8B—C13B	−5.0 (5)	C3C—N2C—C21C—C20C	−59.4 (5)
C6B—C7B—C8B—C13B	114.3 (4)	C19C—C20C—C21C—N2C	−72.0 (5)
C13B—C8B—C9B—C10B	0.8 (7)	C15C—C20C—C21C—N2C	52.7 (5)
C7B—C8B—C9B—C10B	177.0 (5)	C23C—O4C—C22C—O3C	−0.1 (7)
C8B—C9B—C10B—C11B	−0.7 (8)	C23C—O4C—C22C—C16C	179.1 (5)
C9B—C10B—C11B—C12B	0.4 (8)	C17C—C16C—C22C—O3C	176.7 (5)
C10B—C11B—C12B—C13B	−0.3 (8)	C15C—C16C—C22C—O3C	−8.1 (7)
C11B—C12B—C13B—N1B	−179.8 (5)	C17C—C16C—C22C—O4C	−2.5 (7)
C11B—C12B—C13B—C8B	0.5 (8)	C15C—C16C—C22C—O4C	172.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1NA···O1C	0.88	1.99	2.864 (5)	171
N1B—H1NB···O1A	0.88	2.05	2.894 (5)	161
N1C—H1NC···O1B^i	0.88	2.03	2.873 (5)	159
C10B—H10B···O2A^ii	0.95	2.60	3.263 (5)	127
C15C—H15C···O1A	1.00	2.60	3.528 (6)	155
C20A—H20A···O1C^iii	1.00	2.59	3.459 (6)	145

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