Structural analysis of pyrrolidinones

In the course of a study on pyrrolidinones, the crystal structures of four compounds, namely, methyl N-[(4-meth­oxy­phenyl)(3,4,5-tri­meth­oxy­phenyl)­methyl]­pyro­glut­amate, C₂₃­H₂₇­NO₇, methyl N-[naphthyl-(3,4,5-tri­meth­oxy­phenyl)­methyl]­pyro­glut­amate diacetyl peroxide, C₂₆­H₂₇­NO₆·-0.5C₄H₆O₄, 5-(3,4,5-tri­meth­oxy­phenyl)-1,2,3,11b-tetrahy­dro-5H-naphtho­[1,8-f,g]indol­izin-3-one, C₂₄­H₂₃­NO₄, and 5-(3,4,5-tri­meth­oxy­phenyl)-1,2,3,5,12,12a-hexa­hydro­naph­tho­[1,2-f]indol­izine-3,12-dione, C₂₅­H₂₃­NO₅, are presented, compared and discussed.

S1. Comment

Azatoxin, an anti-cancer drug, is an inhibitor of both the topoisomerase II and the tubulin polymerization (Leteurtre et al., 1995). Methyl N-[naphthyl-(3,4,5-trimethoxyphenyl)-methyl] pyroglutamate, (II), is the precursor of 5-(3,4,5-trimethoxyphenyl)-1,2,3,11b-tetrahydro-5H-naphtho[1,8 − f,g] indolizine-3-one, (III), and 5-(3,4,5-trimethoxyphenyl)-1,2,3,5,12,12a-hexahydronaphtho[1,2-f] indolizine-3,12-dione, (IV), two azatoxin analogues. Methyl N-[(4-methoxyphenyl)-(3,4,5-trimethoxyphenyl)-methyl] pyroglutamate, (I), is an aryl derivative of compound (II). Discussion of the geometry is based on the SS enantiomer.

A comparison of the molecular geometries shows the similarity of all bond lengths among the four compounds (Tables 1–4). In all cases (Fig. 1a-d), N18 is found to be clearly of sp² geometry [sums of bond angles around N18 are 360.0 (1), 359.6 (2), 359.9 (1) and 360.0 (2)° for compounds (I), (II), (III) and (IV), respectively] (Tables 1–4). In compound (I), an π-π interaction orients the methyl-ester group just above the trimethoxyphenyl ring, imposing a torsion angle C2—C1—N18—C19 close to 130° (Table 1) which is different from the one obtained in compound (II) where the intramolecular forces orient the methyl ester group just above the naphthyl ring [torsion angle close to 106.0 (2)°] (Table 2). This observation is in agreement with NMR results (Legrand et al., 1999). The formation of the covalent bond to obtain compounds (III) and (IV) does not modify significantly that torsion angle which lies close to 97° (Tables 3 and 4). Moreover, the formation of the covalent bond tends to make the bridged molecules nearly coplanar [N18—C1—C8—C17 for (III) (Table 3) and N18—C1—C8—C9 for (IV) (Table 4)] in comparison with compound (II). The C8—C1—C2—C3 torsion angle varies according to the fact that the molecule is bridged or not (Tables 1–4). In all compounds, the two meta-methoxy groups lie in the same plane than the aromatic ring (torsion angles near 0 or 180°, see Tables 1–4) and the para-methoxy group is out of plane. For the four compounds, the torsion angle of the para-methoxy group is closed to 85° (Tables 1–4). The study of the packing of compound (II) shows the presence of a planar diacetyl-peroxide co-cristallization molecule (torsion angles close to 180°) stacked between two naphthyl rings and situated near an inversion centre (Fig.2) generating the other half of the molecule by symmetry (Table 2). A similar case of a planar peroxide molecule stacked between two aromatic rings has already been cited in the literature (Walter & McBride, 1981).

S2. Experimental

The syntheses of compounds (I)-(IV) have been reported elsewhere (Legrand et al., 1999). Crystals were obtained by slow evaporation of a ethanol solution (compounds (I), (III) and (IV)) or a ethylacetate-diethylether solution (compound (II)) at room temperature.

Computing details

For all compounds, data collection: CAD-4 EXPRESS (Enraf-Nonius, 1992); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. ORTEPII (Johnson, 1976) representation of (a) (I), (b) (II), (c) (III) and (d) (IV) with displacement ellipsoids shown at the 50% level.

(I) 'methyl N-[4-methoxyphenyl-(3,4,5-trimethoxyphenyl)-methyl] pyroglutamate'

Crystal data

C23H27NO7	F(000) = 912
Mr = 429.46	Dx = 1.296 Mg m^−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54178 Å
a = 8.481 (1) Å	Cell parameters from 25 reflections
b = 14.206 (1) Å	θ = 30–42°
c = 18.273 (1) Å	µ = 0.80 mm^−1
β = 90.538 (4)°	T = 293 K
V = 2201.5 (3) Å^3	Prism, colourless
Z = 4	0.30 × 0.30 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3939 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 71.9°, θmin = 3.9°
θ/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→17
Tmin = 0.796, Tmax = 0.857	l = 0→22
6885 measured reflections	3 standard reflections every 200 reflections
4331 independent reflections	intensity decay: 2%

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.122	Calculated w = 1/[σ^2(Fo^2) + (0.0648P)^2 + 0.5599P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
4331 reflections	Δρmax = 0.30 e Å^−3
283 parameters	Δρmin = −0.24 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0104 (5)

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
C1	0.18619 (14)	1.00402 (9)	0.61066 (7)	0.0361 (3)
H1	0.1554	0.9556	0.5751	0.041 (4)*
C2	0.09036 (15)	0.98528 (10)	0.67946 (7)	0.0374 (3)
C3	0.07918 (16)	1.05288 (10)	0.73415 (7)	0.0418 (3)
H3	0.1264	1.1114	0.7281	0.050*
C4	−0.00259 (16)	1.03301 (10)	0.79801 (7)	0.0429 (3)
C5	−0.08024 (16)	0.94753 (11)	0.80531 (8)	0.0444 (3)
C6	−0.07112 (17)	0.88028 (10)	0.74967 (8)	0.0457 (3)
C7	0.01611 (16)	0.89900 (10)	0.68711 (8)	0.0426 (3)
H7	0.0245	0.8537	0.6506	0.051*
C8	0.14805 (14)	1.09832 (9)	0.57526 (7)	0.0357 (3)
C9	−0.00909 (15)	1.11973 (10)	0.55837 (8)	0.0430 (3)
H9	−0.0877	1.0772	0.5709	0.052*
C10	−0.05032 (16)	1.20224 (11)	0.52363 (8)	0.0474 (3)
H10	−0.1557	1.2146	0.5128	0.057*
C11	0.06505 (17)	1.26717 (10)	0.50473 (7)	0.0423 (3)
C12	0.22165 (16)	1.24640 (10)	0.51951 (8)	0.0423 (3)
H12	0.3002	1.2886	0.5063	0.051*
C13	0.26136 (15)	1.16236 (10)	0.55424 (7)	0.0399 (3)
H13	0.3670	1.1490	0.5635	0.048*
N18	0.35550 (12)	0.99215 (8)	0.62385 (6)	0.0364 (3)
C19	0.44662 (15)	0.93779 (10)	0.58019 (7)	0.0396 (3)
C20	0.61516 (16)	0.94527 (11)	0.60725 (9)	0.0487 (4)
H20A	0.6868	0.9543	0.5668	0.058*
H20B	0.6460	0.8891	0.6340	0.058*
C21	0.61482 (16)	1.03054 (11)	0.65699 (8)	0.0470 (3)
H21A	0.6447	1.0868	0.6305	0.056*
H21B	0.6868	1.0219	0.6980	0.056*
C22	0.44251 (16)	1.03722 (10)	0.68332 (7)	0.0397 (3)
H22	0.4111	1.1034	0.6872	0.039 (4)*
O23	−0.01575 (15)	1.09367 (8)	0.85571 (6)	0.0587 (3)
C24	0.0839 (3)	1.17375 (14)	0.85756 (11)	0.0748 (6)
H24A	0.0562	1.2152	0.8180	0.112*
H24B	0.1916	1.1542	0.8527	0.112*
H24C	0.0712	1.2061	0.9033	0.112*
O25	−0.17314 (14)	0.93136 (9)	0.86548 (6)	0.0590 (3)
C26	−0.0987 (3)	0.8828 (2)	0.92358 (12)	0.0932 (8)
H26A	−0.0708	0.8206	0.9078	0.140*
H26B	−0.1694	0.8787	0.9642	0.140*
H26C	−0.0052	0.9162	0.9383	0.140*
O27	−0.15295 (16)	0.79920 (9)	0.76148 (7)	0.0674 (4)
C28	−0.1511 (3)	0.72962 (12)	0.70627 (12)	0.0687 (5)
H28A	−0.1929	0.7554	0.6616	0.103*
H28B	−0.2143	0.6770	0.7211	0.103*
H28C	−0.0446	0.7091	0.6987	0.103*
O29	0.39798 (12)	0.89150 (8)	0.52828 (6)	0.0542 (3)
C30	0.42565 (18)	0.98921 (11)	0.75696 (8)	0.0471 (3)
O31	0.42619 (18)	0.89685 (9)	0.75173 (6)	0.0674 (4)
C32	0.4234 (4)	0.84702 (18)	0.82092 (11)	0.1054 (10)
H32A	0.4593	0.7836	0.8139	0.158*
H32B	0.3177	0.8461	0.8392	0.158*
H32C	0.4913	0.8783	0.8555	0.158*
O33	0.42047 (17)	1.03188 (10)	0.81374 (6)	0.0695 (4)
O34	0.01323 (13)	1.34787 (8)	0.47215 (6)	0.0580 (3)
C35	0.1273 (2)	1.41870 (12)	0.45689 (10)	0.0614 (4)
H35A	0.0760	1.4720	0.4348	0.092*
H35B	0.2045	1.3940	0.4239	0.092*
H35C	0.1783	1.4377	0.5016	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0304 (6)	0.0425 (7)	0.0353 (6)	−0.0017 (5)	0.0017 (5)	−0.0029 (5)
C2	0.0331 (6)	0.0421 (7)	0.0371 (6)	0.0012 (5)	0.0029 (5)	0.0016 (5)
C3	0.0421 (7)	0.0408 (7)	0.0426 (7)	−0.0027 (5)	0.0075 (5)	−0.0004 (5)
C4	0.0412 (7)	0.0479 (8)	0.0397 (7)	0.0053 (6)	0.0058 (5)	−0.0010 (6)
C5	0.0386 (7)	0.0522 (8)	0.0424 (7)	0.0042 (6)	0.0092 (5)	0.0083 (6)
C6	0.0406 (7)	0.0444 (8)	0.0522 (8)	−0.0037 (6)	0.0045 (6)	0.0070 (6)
C7	0.0411 (7)	0.0418 (7)	0.0448 (7)	−0.0014 (6)	0.0034 (6)	−0.0016 (6)
C8	0.0331 (6)	0.0432 (7)	0.0307 (6)	0.0001 (5)	0.0028 (5)	−0.0024 (5)
C9	0.0311 (6)	0.0512 (8)	0.0465 (7)	−0.0046 (6)	0.0014 (5)	0.0029 (6)
C10	0.0319 (6)	0.0584 (9)	0.0517 (8)	0.0031 (6)	−0.0037 (6)	0.0045 (7)
C11	0.0437 (7)	0.0475 (8)	0.0356 (6)	0.0045 (6)	0.0001 (5)	0.0019 (5)
C12	0.0368 (7)	0.0478 (8)	0.0425 (7)	−0.0042 (6)	0.0040 (5)	0.0031 (6)
C13	0.0300 (6)	0.0492 (8)	0.0406 (7)	0.0002 (5)	0.0025 (5)	0.0010 (6)
N18	0.0324 (5)	0.0432 (6)	0.0336 (5)	0.0015 (4)	−0.0002 (4)	−0.0025 (4)
C19	0.0356 (7)	0.0432 (7)	0.0400 (7)	0.0018 (5)	0.0038 (5)	−0.0004 (5)
C20	0.0352 (7)	0.0595 (9)	0.0513 (8)	0.0058 (6)	−0.0002 (6)	−0.0044 (7)
C21	0.0361 (7)	0.0546 (8)	0.0502 (8)	−0.0019 (6)	−0.0033 (6)	−0.0007 (6)
C22	0.0391 (7)	0.0415 (7)	0.0383 (7)	−0.0006 (5)	−0.0035 (5)	−0.0025 (5)
O23	0.0693 (7)	0.0593 (7)	0.0478 (6)	−0.0032 (5)	0.0189 (5)	−0.0102 (5)
C24	0.0971 (15)	0.0654 (11)	0.0622 (11)	−0.0137 (10)	0.0195 (10)	−0.0218 (9)
O25	0.0548 (6)	0.0706 (8)	0.0520 (6)	0.0025 (5)	0.0201 (5)	0.0133 (5)
C26	0.1013 (17)	0.117 (2)	0.0619 (12)	0.0127 (15)	0.0163 (11)	0.0370 (12)
O27	0.0775 (8)	0.0546 (7)	0.0706 (8)	−0.0223 (6)	0.0196 (6)	0.0025 (6)
C28	0.0785 (12)	0.0412 (8)	0.0864 (13)	−0.0104 (8)	−0.0021 (10)	0.0056 (8)
O29	0.0417 (5)	0.0682 (7)	0.0527 (6)	−0.0008 (5)	0.0036 (4)	−0.0217 (5)
C30	0.0473 (8)	0.0565 (9)	0.0374 (7)	−0.0016 (6)	−0.0035 (6)	−0.0021 (6)
O31	0.1094 (11)	0.0526 (7)	0.0402 (6)	−0.0051 (6)	0.0004 (6)	0.0082 (5)
C32	0.188 (3)	0.0769 (15)	0.0511 (11)	−0.0193 (17)	0.0004 (14)	0.0245 (10)
O33	0.0889 (9)	0.0815 (9)	0.0381 (6)	0.0027 (7)	−0.0064 (6)	−0.0116 (6)
O34	0.0525 (6)	0.0573 (7)	0.0642 (7)	0.0058 (5)	−0.0023 (5)	0.0183 (5)
C35	0.0695 (11)	0.0513 (9)	0.0633 (10)	0.0006 (8)	0.0001 (8)	0.0146 (8)

Geometric parameters (Å, º)

C1—N18	1.464 (2)	C13—H13	0.9300
C1—C8	1.521 (2)	C19—O29	1.223 (2)
C1—C2	1.527 (2)	C20—H20A	0.9700
N18—C19	1.357 (2)	C20—H20B	0.9700
N18—C22	1.456 (2)	C21—H21A	0.9700
C19—C20	1.512 (2)	C21—H21B	0.9700
C20—C21	1.514 (2)	C22—C30	1.517 (2)
C21—C22	1.546 (2)	C22—H22	0.9800
C1—H1	0.9800	O23—C24	1.417 (2)
C2—C7	1.386 (2)	C24—H24A	0.9600
C2—C3	1.390 (2)	C24—H24B	0.9600
C3—C4	1.392 (2)	C24—H24C	0.9600
C3—H3	0.9300	O25—C26	1.410 (2)
C4—O23	1.367 (2)	C26—H26A	0.9600
C4—C5	1.388 (2)	C26—H26B	0.9600
C5—O25	1.378 (2)	C26—H26C	0.9600
C5—C6	1.398 (2)	O27—C28	1.412 (2)
C6—O27	1.363 (2)	C28—H28A	0.9600
C6—C7	1.393 (2)	C28—H28B	0.9600
C7—H7	0.9300	C28—H28C	0.9600
C8—C13	1.380 (2)	C30—O33	1.203 (2)
C8—C9	1.399 (2)	C30—O31	1.316 (2)
C9—C10	1.377 (2)	O31—C32	1.449 (2)
C9—H9	0.9300	C32—H32A	0.9600
C10—C11	1.391 (2)	C32—H32B	0.9600
C10—H10	0.9300	C32—H32C	0.9600
C11—O34	1.363 (2)	O34—C35	1.425 (2)
C11—C12	1.385 (2)	C35—H35A	0.9600
C12—C13	1.392 (2)	C35—H35B	0.9600
C12—H12	0.9300	C35—H35C	0.9600
N18—C1—C8	112.08 (10)	C21—C20—H20B	110.9
N18—C1—C2	111.92 (10)	H20A—C20—H20B	108.9
C8—C1—C2	113.02 (10)	C20—C21—C22	104.06 (11)
N18—C1—H1	106.4	C20—C21—H21A	110.9
C8—C1—H1	106.4	C22—C21—H21A	110.9
C2—C1—H1	106.4	C20—C21—H21B	110.9
C7—C2—C3	120.29 (12)	C22—C21—H21B	110.9
C7—C2—C1	118.90 (12)	H21A—C21—H21B	109.0
C3—C2—C1	120.80 (12)	N18—C22—C30	114.40 (11)
C2—C3—C4	120.04 (13)	N18—C22—C21	102.40 (10)
C2—C3—H3	120.0	C30—C22—C21	110.23 (12)
C4—C3—H3	120.0	N18—C22—H22	109.9
O23—C4—C5	115.79 (12)	C30—C22—H22	109.9
O23—C4—C3	124.31 (13)	C21—C22—H22	109.9
C5—C4—C3	119.89 (13)	C4—O23—C24	118.13 (12)
O25—C5—C4	119.84 (14)	O23—C24—H24A	109.5
O25—C5—C6	120.16 (14)	O23—C24—H24B	109.5
C4—C5—C6	119.90 (13)	H24A—C24—H24B	109.5
O27—C6—C7	124.50 (14)	O23—C24—H24C	109.5
O27—C6—C5	115.52 (13)	H24A—C24—H24C	109.5
C7—C6—C5	119.98 (13)	H24B—C24—H24C	109.5
C2—C7—C6	119.81 (13)	C5—O25—C26	115.26 (14)
C2—C7—H7	120.1	O25—C26—H26A	109.5
C6—C7—H7	120.1	O25—C26—H26B	109.5
C13—C8—C9	117.36 (12)	H26A—C26—H26B	109.5
C13—C8—C1	123.57 (11)	O25—C26—H26C	109.5
C9—C8—C1	118.93 (11)	H26A—C26—H26C	109.5
C10—C9—C8	121.63 (13)	H26B—C26—H26C	109.5
C10—C9—H9	119.2	C6—O27—C28	117.98 (13)
C8—C9—H9	119.2	O27—C28—H28A	109.5
C9—C10—C11	120.20 (13)	O27—C28—H28B	109.5
C9—C10—H10	119.9	H28A—C28—H28B	109.5
C11—C10—H10	119.9	O27—C28—H28C	109.5
O34—C11—C12	124.71 (13)	H28A—C28—H28C	109.5
O34—C11—C10	116.21 (13)	H28B—C28—H28C	109.5
C12—C11—C10	119.08 (13)	O33—C30—O31	124.44 (15)
C11—C12—C13	119.95 (13)	O33—C30—C22	122.90 (15)
C11—C12—H12	120.0	O31—C30—C22	112.56 (12)
C13—C12—H12	120.0	C30—O31—C32	115.06 (15)
C8—C13—C12	121.74 (12)	O31—C32—H32A	109.5
C8—C13—H13	119.1	O31—C32—H32B	109.5
C12—C13—H13	119.1	H32A—C32—H32B	109.5
C19—N18—C22	113.7 (1)	O31—C32—H32C	109.5
C19—N18—C1	122.1 (1)	H32A—C32—H32C	109.5
C22—N18—C1	124.2 (1)	H32B—C32—H32C	109.5
O29—C19—N18	124.91 (12)	C11—O34—C35	117.56 (12)
O29—C19—C20	127.06 (12)	O34—C35—H35A	109.5
N18—C19—C20	108.03 (11)	O34—C35—H35B	109.5
C19—C20—C21	104.21 (11)	H35A—C35—H35B	109.5
C19—C20—H20A	110.9	O34—C35—H35C	109.5
C21—C20—H20A	110.9	H35A—C35—H35C	109.5
C19—C20—H20B	110.9	H35B—C35—H35C	109.5
N18—C1—C2—C7	−100.44 (14)	C11—C12—C13—C8	−0.5 (2)
C8—C1—C2—C7	131.88 (13)	C8—C1—N18—C19	−102.61 (14)
N18—C1—C2—C3	78.68 (16)	C2—C1—N18—C19	129.2 (1)
C8—C1—C2—C3	−49.0 (2)	C8—C1—N18—C22	76.66 (15)
C7—C2—C3—C4	2.1 (2)	C2—C1—N18—C22	−51.51 (16)
C1—C2—C3—C4	−177.03 (12)	C22—N18—C19—O29	177.95 (14)
C2—C3—C4—O23	177.82 (13)	C1—N18—C19—O29	−2.7 (2)
C2—C3—C4—C5	−3.5 (2)	C22—N18—C19—C20	−2.09 (16)
O23—C4—C5—O25	4.8 (2)	C1—N18—C19—C20	177.25 (12)
C3—C4—C5—O25	−173.98 (13)	O29—C19—C20—C21	164.46 (15)
O23—C4—C5—C6	−178.83 (13)	N18—C19—C20—C21	−15.50 (16)
C3—C4—C5—C6	2.4 (2)	C19—C20—C21—C22	25.71 (15)
O25—C5—C6—O27	−2.8 (2)	C19—N18—C22—C30	−100.98 (14)
C4—C5—C6—O27	−179.17 (13)	C1—N18—C22—C30	79.70 (16)
O25—C5—C6—C7	176.54 (13)	C19—N18—C22—C21	18.27 (15)
C4—C5—C6—C7	0.2 (2)	C1—N18—C22—C21	−161.05 (12)
C3—C2—C7—C6	0.5 (2)	C20—C21—C22—N18	−26.49 (14)
C1—C2—C7—C6	179.62 (12)	C20—C21—C22—C30	95.64 (14)
O27—C6—C7—C2	177.66 (14)	C5—C4—O23—C24	168.4 (2)
C5—C6—C7—C2	−1.6 (2)	C3—C4—O23—C24	−12.9 (2)
N18—C1—C8—C13	3.62 (17)	C4—C5—O25—C26	−95.7 (2)
C2—C1—C8—C13	131.21 (13)	C6—C5—O25—C26	87.9 (2)
N18—C1—C8—C9	179.25 (11)	C7—C6—O27—C28	−0.8 (2)
C2—C1—C8—C9	−53.16 (16)	C5—C6—O27—C28	178.52 (15)
C13—C8—C9—C10	−1.4 (2)	N18—C22—C30—O33	−144.00 (15)
C1—C8—C9—C10	−177.33 (13)	C21—C22—C30—O33	101.26 (18)
C8—C9—C10—C11	−0.4 (2)	N18—C22—C30—O31	39.48 (18)
C9—C10—C11—O34	−178.44 (13)	C21—C22—C30—O31	−75.26 (16)
C9—C10—C11—C12	1.8 (2)	O33—C30—O31—C32	−1.3 (3)
O34—C11—C12—C13	178.88 (13)	C22—C30—O31—C32	175.18 (19)
C10—C11—C12—C13	−1.3 (2)	C12—C11—O34—C35	−4.6 (2)
C9—C8—C13—C12	1.9 (2)	C10—C11—O34—C35	175.60 (14)
C1—C8—C13—C12	177.56 (12)

(II) 'methyl N-[naphtyl-(3,4,5-trimethoxyphenyl)-methyl] pyroglutamate'

Crystal data

C26H27NO6·0.5C4H6O4	Z = 2
Mr = 508.55	F(000) = 538
Triclinic, P1	Dx = 1.253 Mg m^−3
a = 9.190 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 11.333 (1) Å	Cell parameters from 25 reflections
c = 14.756 (1) Å	θ = 30–42°
α = 89.292 (7)°	µ = 0.76 mm^−1
β = 73.923 (5)°	T = 293 K
γ = 66.722 (7)°	Prism, colourless
V = 1348.3 (2) Å^3	0.40 × 0.30 × 0.30 mm

Data collection

Enraf-Nonius CAD4 diffractometer	4947 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.008
Graphite monochromator	θmax = 72.0°, θmin = 3.1°
θ/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→13
Tmin = 0.750, Tmax = 0.804	l = −17→18
5621 measured reflections	3 standard reflections every 200 reflections
5274 independent reflections	intensity decay: 8%

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)] = 0.065	H-atom parameters constrained
wR(F^2) = 0.210	Calculated w = 1/[σ^2(Fo^2) + (0.1495P)^2 + 0.3694P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.002
5274 reflections	Δρmax = 0.35 e Å^−3
311 parameters	Δρmin = −0.60 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0127 (15)

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
C1	0.5886 (2)	0.27411 (15)	0.31654 (11)	0.0386 (4)
H1	0.6833	0.2977	0.2942	0.046*
C2	0.6384 (2)	0.16590 (15)	0.37973 (11)	0.0384 (4)
C3	0.7774 (2)	0.05361 (16)	0.33777 (12)	0.0453 (4)
H3	0.8319	0.0448	0.2733	0.054*
C4	0.8348 (2)	−0.04567 (16)	0.39234 (13)	0.0464 (4)
C5	0.7514 (2)	−0.03328 (16)	0.48855 (13)	0.0440 (4)
C6	0.6137 (2)	0.07988 (16)	0.52988 (12)	0.0435 (4)
C7	0.5564 (2)	0.18019 (15)	0.47546 (12)	0.0411 (4)
H7	0.4641	0.2558	0.5034	0.049*
C8	0.5602 (2)	0.23088 (16)	0.22820 (12)	0.0432 (4)
C9	0.4870 (3)	0.14584 (19)	0.23293 (14)	0.0536 (5)
H9	0.4585	0.1124	0.2898	0.064*
C10	0.4543 (3)	0.1082 (3)	0.15245 (19)	0.0739 (7)
H10	0.4026	0.0516	0.1566	0.089*
C11	0.4990 (4)	0.1553 (3)	0.06841 (18)	0.0847 (9)
H11	0.4784	0.1292	0.0155	0.102*
C12	0.5748 (3)	0.2419 (2)	0.06010 (14)	0.0714 (7)
C13	0.6047 (2)	0.28285 (19)	0.14108 (13)	0.0535 (5)
C14	0.6742 (3)	0.3758 (2)	0.13209 (17)	0.0685 (6)
H14	0.6921	0.4061	0.1845	0.082*
C15	0.7151 (4)	0.4208 (3)	0.0464 (2)	0.0955 (10)
H15	0.7609	0.4814	0.0415	0.115*
C16	0.6898 (5)	0.3785 (4)	−0.0332 (2)	0.1068 (13)
H16	0.7199	0.4097	−0.0909	0.128*
C17	0.6215 (4)	0.2921 (4)	−0.02692 (17)	0.1017 (12)
H17	0.6045	0.2645	−0.0807	0.122*
N18	0.44802 (16)	0.39130 (12)	0.36730 (10)	0.0380 (3)
C19	0.4669 (2)	0.49951 (16)	0.38944 (13)	0.0440 (4)
C20	0.2972 (2)	0.60317 (17)	0.43823 (15)	0.0524 (5)
H20A	0.2976	0.6454	0.4949	0.063*
H20B	0.2614	0.6677	0.3961	0.063*
C21	0.1859 (2)	0.53162 (19)	0.46303 (13)	0.0510 (4)
H21A	0.0766	0.5840	0.4576	0.061*
H21B	0.1750	0.5075	0.5271	0.061*
C22	0.27548 (19)	0.41026 (15)	0.38917 (11)	0.0395 (4)
H22	0.2586	0.3356	0.4162	0.047*
O23	0.9706 (2)	−0.15873 (13)	0.35836 (11)	0.0663 (4)
C24	1.0636 (4)	−0.1725 (2)	0.26162 (18)	0.0843 (8)
H24A	0.9971	−0.1736	0.2219	0.126*
H24B	1.1611	−0.2520	0.2477	0.126*
H24C	1.0954	−0.1013	0.2499	0.126*
O25	0.80486 (18)	−0.13426 (12)	0.54138 (10)	0.0532 (4)
C26	0.9158 (3)	−0.1240 (2)	0.58771 (18)	0.0651 (6)
H26A	1.0108	−0.1211	0.5415	0.098*
H26B	0.9508	−0.1976	0.6220	0.098*
H26C	0.8612	−0.0465	0.6311	0.098*
O27	0.54268 (19)	0.08387 (14)	0.62471 (9)	0.0602 (4)
C28	0.3996 (3)	0.1962 (2)	0.67110 (16)	0.0715 (7)
H28A	0.4278	0.2695	0.6676	0.107*
H28B	0.3592	0.1846	0.7364	0.107*
H28C	0.3152	0.2104	0.6407	0.107*
O29	0.60001 (17)	0.50816 (13)	0.37215 (11)	0.0587 (4)
C30	0.2108 (2)	0.44251 (16)	0.30357 (12)	0.0430 (4)
O31	0.09221 (19)	0.40095 (18)	0.30890 (11)	0.0663 (4)
C32	0.0102 (4)	0.4348 (5)	0.2364 (2)	0.1062 (12)
H32A	−0.0313	0.5266	0.2342	0.159*
H32B	−0.0803	0.4086	0.2506	0.159*
H32C	0.0875	0.3918	0.1761	0.159*
O33	0.25318 (18)	0.50323 (14)	0.24303 (10)	0.0582 (4)
O41	0.9701 (4)	0.9573 (3)	0.0268 (2)	0.133
O42	0.9245 (6)	0.9144 (5)	−0.0945 (4)	0.193
C43	0.9221 (8)	0.8998 (7)	−0.0188 (6)	0.168
C44	0.8624 (11)	0.8072 (9)	0.0284 (6)	0.219
H44A	0.8314	0.7662	−0.0150	0.329*
H44B	0.7678	0.8513	0.0823	0.329*
H44C	0.9487	0.7431	0.0490	0.329*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0405 (8)	0.0342 (7)	0.0396 (8)	−0.0140 (6)	−0.0116 (6)	0.0094 (6)
C2	0.0441 (8)	0.0341 (7)	0.0411 (8)	−0.0171 (6)	−0.0172 (6)	0.0087 (6)
C3	0.0509 (9)	0.0401 (9)	0.0399 (8)	−0.0123 (7)	−0.0153 (7)	0.0079 (7)
C4	0.0522 (9)	0.0352 (8)	0.0498 (9)	−0.0125 (7)	−0.0202 (8)	0.0075 (7)
C5	0.0553 (9)	0.0363 (8)	0.0495 (9)	−0.0225 (7)	−0.0239 (8)	0.0154 (7)
C6	0.0544 (9)	0.0424 (8)	0.0402 (8)	−0.0255 (7)	−0.0155 (7)	0.0114 (7)
C7	0.0465 (8)	0.0348 (7)	0.0428 (8)	−0.0167 (6)	−0.0143 (7)	0.0079 (6)
C8	0.0430 (8)	0.0396 (8)	0.0378 (8)	−0.0078 (6)	−0.0118 (6)	0.0067 (6)
C9	0.0606 (11)	0.0493 (10)	0.0511 (10)	−0.0194 (8)	−0.0212 (8)	0.0024 (8)
C10	0.0823 (16)	0.0693 (14)	0.0725 (15)	−0.0233 (12)	−0.0370 (12)	−0.0080 (11)
C11	0.0878 (17)	0.0887 (18)	0.0573 (14)	−0.0044 (14)	−0.0372 (12)	−0.0172 (12)
C12	0.0694 (13)	0.0678 (13)	0.0390 (10)	0.0094 (11)	−0.0141 (9)	−0.0002 (9)
C13	0.0478 (9)	0.0513 (10)	0.0385 (9)	−0.0009 (8)	−0.0074 (7)	0.0105 (7)
C14	0.0630 (12)	0.0637 (12)	0.0592 (12)	−0.0151 (10)	−0.0054 (10)	0.0276 (10)
C15	0.0903 (19)	0.0862 (18)	0.0724 (18)	−0.0173 (15)	0.0035 (14)	0.0406 (15)
C16	0.111 (2)	0.096 (2)	0.0517 (15)	0.0014 (19)	0.0032 (14)	0.0337 (15)
C17	0.104 (2)	0.100 (2)	0.0382 (11)	0.0164 (18)	−0.0125 (12)	0.0086 (12)
N18	0.0381 (7)	0.0326 (6)	0.0439 (7)	−0.0143 (5)	−0.0133 (5)	0.0075 (5)
C19	0.0498 (9)	0.0357 (8)	0.0511 (9)	−0.0190 (7)	−0.0200 (7)	0.0099 (7)
C20	0.0538 (10)	0.0375 (9)	0.0635 (11)	−0.0137 (7)	−0.0207 (9)	−0.0005 (7)
C21	0.0468 (9)	0.0523 (10)	0.0467 (9)	−0.0160 (8)	−0.0091 (7)	−0.0025 (7)
C22	0.0401 (8)	0.0391 (8)	0.0401 (8)	−0.0179 (6)	−0.0108 (6)	0.0083 (6)
O23	0.0728 (9)	0.0426 (7)	0.0577 (8)	0.0014 (6)	−0.0174 (7)	0.0098 (6)
C24	0.0926 (18)	0.0547 (12)	0.0579 (13)	0.0090 (12)	−0.0083 (12)	0.0040 (10)
O25	0.0707 (8)	0.0435 (7)	0.0599 (8)	−0.0291 (6)	−0.0331 (7)	0.0243 (6)
C26	0.0751 (14)	0.0613 (12)	0.0736 (14)	−0.0292 (11)	−0.0429 (11)	0.0265 (10)
O27	0.0753 (9)	0.0545 (8)	0.0426 (7)	−0.0242 (7)	−0.0091 (6)	0.0165 (6)
C28	0.0921 (17)	0.0582 (12)	0.0500 (11)	−0.0320 (12)	0.0023 (11)	0.0061 (9)
O29	0.0527 (7)	0.0494 (7)	0.0829 (10)	−0.0283 (6)	−0.0222 (7)	0.0087 (7)
C30	0.0391 (8)	0.0430 (8)	0.0428 (8)	−0.0130 (7)	−0.0115 (6)	0.0050 (7)
O31	0.0584 (8)	0.0976 (12)	0.0616 (9)	−0.0444 (8)	−0.0275 (7)	0.0185 (8)
C32	0.0859 (19)	0.180 (4)	0.0851 (19)	−0.069 (2)	−0.0539 (17)	0.029 (2)
O33	0.0592 (8)	0.0609 (8)	0.0523 (8)	−0.0214 (7)	−0.0186 (6)	0.0226 (6)
O41	0.133	0.133	0.133	−0.054	−0.039	0.015
O42	0.193	0.193	0.193	−0.079	−0.057	0.021
C43	0.168	0.168	0.168	−0.068	−0.050	0.018
C44	0.219	0.219	0.219	−0.089	−0.065	0.024

Geometric parameters (Å, º)

C1—N18	1.458 (2)	C19—O29	1.221 (2)
C1—C8	1.521 (2)	C19—C20	1.510 (2)
C1—C2	1.532 (2)	C20—C21	1.510 (3)
C1—H1	0.9800	C20—H20A	0.9700
C2—C7	1.381 (2)	C20—H20B	0.9700
C2—C3	1.390 (2)	C21—C22	1.550 (2)
C3—C4	1.392 (2)	C21—H21A	0.9700
C3—H3	0.9300	C21—H21B	0.9700
C4—O23	1.362 (2)	C22—C30	1.521 (2)
C4—C5	1.393 (3)	C22—H22	0.9800
C5—O25	1.3800 (19)	O23—C24	1.420 (3)
C5—C6	1.388 (3)	C24—H24A	0.9600
C6—O27	1.363 (2)	C24—H24B	0.9600
C6—C7	1.398 (2)	C24—H24C	0.9600
C7—H7	0.9300	O25—C26	1.415 (2)
C8—C9	1.368 (3)	C26—H26A	0.9600
C8—C13	1.431 (2)	C26—H26B	0.9600
C9—C10	1.412 (3)	C26—H26C	0.9600
C9—H9	0.9300	O27—C28	1.421 (3)
C10—C11	1.366 (4)	C28—H28A	0.9600
C10—H10	0.9300	C28—H28B	0.9600
C11—C12	1.398 (4)	C28—H28C	0.9600
C11—H11	0.9300	C30—O33	1.195 (2)
C12—C13	1.419 (3)	C30—O31	1.332 (2)
C12—C17	1.423 (4)	O31—C32	1.437 (3)
C13—C14	1.420 (3)	C32—H32A	0.9600
C14—C15	1.369 (3)	C32—H32B	0.9600
C14—H14	0.9300	C32—H32C	0.9600
C15—C16	1.384 (6)	O41—C43	1.214 (7)
C15—H15	0.9300	O41—O41^i	1.424 (6)
C16—C17	1.346 (6)	O42—C43	1.123 (8)
C16—H16	0.9300	C43—C44	1.453 (10)
C17—H17	0.9300	C44—H44A	0.9600
N18—C19	1.360 (2)	C44—H44B	0.9600
N18—C22	1.454 (2)	C44—H44C	0.9600
N18—C1—C8	110.88 (13)	C21—C20—C19	104.39 (14)
N18—C1—C2	113.47 (13)	C21—C20—H20A	110.9
C8—C1—C2	113.11 (13)	C19—C20—H20A	110.9
N18—C1—H1	106.3	C21—C20—H20B	110.9
C8—C1—H1	106.3	C19—C20—H20B	110.9
C2—C1—H1	106.3	H20A—C20—H20B	108.9
C7—C2—C3	120.59 (15)	C20—C21—C22	103.95 (14)
C7—C2—C1	122.37 (14)	C20—C21—H21A	111.0
C3—C2—C1	116.94 (14)	C22—C21—H21A	111.0
C2—C3—C4	119.92 (16)	C20—C21—H21B	111.0
C2—C3—H3	120.0	C22—C21—H21B	111.0
C4—C3—H3	120.0	H21A—C21—H21B	109.0
O23—C4—C3	124.50 (17)	N18—C22—C30	112.12 (13)
O23—C4—C5	115.51 (15)	N18—C22—C21	102.21 (13)
C3—C4—C5	119.99 (16)	C30—C22—C21	108.16 (14)
O25—C5—C6	120.73 (16)	N18—C22—H22	111.3
O25—C5—C4	119.71 (16)	C30—C22—H22	111.3
C6—C5—C4	119.55 (15)	C21—C22—H22	111.3
O27—C6—C5	115.20 (15)	C4—O23—C24	117.20 (15)
O27—C6—C7	124.21 (16)	O23—C24—H24A	109.5
C5—C6—C7	120.59 (16)	O23—C24—H24B	109.5
C2—C7—C6	119.34 (16)	H24A—C24—H24B	109.5
C2—C7—H7	120.3	O23—C24—H24C	109.5
C6—C7—H7	120.3	H24A—C24—H24C	109.5
C9—C8—C13	120.10 (18)	H24B—C24—H24C	109.5
C9—C8—C1	119.98 (15)	C5—O25—C26	113.12 (14)
C13—C8—C1	119.89 (16)	O25—C26—H26A	109.5
C8—C9—C10	120.7 (2)	O25—C26—H26B	109.5
C8—C9—H9	119.6	H26A—C26—H26B	109.5
C10—C9—H9	119.6	O25—C26—H26C	109.5
C11—C10—C9	119.7 (3)	H26A—C26—H26C	109.5
C11—C10—H10	120.1	H26B—C26—H26C	109.5
C9—C10—H10	120.1	C6—O27—C28	118.06 (16)
C10—C11—C12	121.5 (2)	O27—C28—H28A	109.5
C10—C11—H11	119.2	O27—C28—H28B	109.5
C12—C11—H11	119.2	H28A—C28—H28B	109.5
C11—C12—C13	119.3 (2)	O27—C28—H28C	109.5
C11—C12—C17	122.1 (3)	H28A—C28—H28C	109.5
C13—C12—C17	118.6 (3)	H28B—C28—H28C	109.5
C12—C13—C14	118.2 (2)	O33—C30—O31	124.59 (17)
C12—C13—C8	118.6 (2)	O33—C30—C22	124.89 (16)
C14—C13—C8	123.13 (19)	O31—C30—C22	110.37 (14)
C15—C14—C13	120.1 (3)	C30—O31—C32	116.2 (2)
C15—C14—H14	119.9	O31—C32—H32A	109.5
C13—C14—H14	119.9	O31—C32—H32B	109.5
C14—C15—C16	121.7 (3)	H32A—C32—H32B	109.5
C14—C15—H15	119.2	O31—C32—H32C	109.5
C16—C15—H15	119.2	H32A—C32—H32C	109.5
C17—C16—C15	119.8 (3)	H32B—C32—H32C	109.5
C17—C16—H16	120.1	C43—O41—O41^i	112.4 (6)
C15—C16—H16	120.1	O42—C43—O41	122.9 (8)
C16—C17—C12	121.5 (3)	O42—C43—C44	120.1 (8)
C16—C17—H17	119.2	O41—C43—C44	117.0 (8)
C12—C17—H17	119.2	C43—C44—H44A	109.5
C19—N18—C22	113.3 (1)	C43—C44—H44B	109.5
C19—N18—C1	122.0 (1)	H44A—C44—H44B	109.5
C22—N18—C1	124.4 (1)	C43—C44—H44C	109.5
O29—C19—N18	124.61 (16)	H44A—C44—H44C	109.5
O29—C19—C20	127.27 (16)	H44B—C44—H44C	109.5
N18—C19—C20	108.12 (14)
N18—C1—C2—C7	−0.1 (2)	C12—C13—C14—C15	−1.8 (3)
C8—C1—C2—C7	−127.55 (16)	C8—C13—C14—C15	179.5 (2)
N18—C1—C2—C3	−176.42 (14)	C13—C14—C15—C16	0.3 (4)
C8—C1—C2—C3	56.2 (2)	C14—C15—C16—C17	0.8 (5)
C7—C2—C3—C4	0.1 (3)	C15—C16—C17—C12	−0.3 (5)
C1—C2—C3—C4	176.44 (15)	C11—C12—C17—C16	177.9 (3)
C2—C3—C4—O23	−179.27 (17)	C13—C12—C17—C16	−1.3 (4)
C2—C3—C4—C5	1.1 (3)	C8—C1—N18—C19	−125.41 (16)
O23—C4—C5—O25	−2.5 (2)	C2—C1—N18—C19	106.0 (2)
C3—C4—C5—O25	177.24 (16)	C8—C1—N18—C22	47.08 (19)
O23—C4—C5—C6	178.61 (16)	C2—C1—N18—C22	−81.50 (18)
C3—C4—C5—C6	−1.7 (3)	C22—N18—C19—O29	−175.49 (16)
O25—C5—C6—O27	2.4 (2)	C1—N18—C19—O29	−2.2 (3)
C4—C5—C6—O27	−178.68 (16)	C22—N18—C19—C20	4.72 (19)
O25—C5—C6—C7	−177.73 (15)	C1—N18—C19—C20	177.97 (14)
C4—C5—C6—C7	1.2 (3)	O29—C19—C20—C21	−165.94 (19)
C3—C2—C7—C6	−0.6 (2)	N18—C19—C20—C21	13.8 (2)
C1—C2—C7—C6	−176.75 (14)	C19—C20—C21—C22	−25.43 (19)
O27—C6—C7—C2	179.82 (15)	C19—N18—C22—C30	95.04 (17)
C5—C6—C7—C2	0.0 (3)	C1—N18—C22—C30	−78.03 (18)
N18—C1—C8—C9	−91.31 (18)	C19—N18—C22—C21	−20.58 (18)
C2—C1—C8—C9	37.5 (2)	C1—N18—C22—C21	166.36 (14)
N18—C1—C8—C13	86.5 (2)	C20—C21—C22—N18	27.62 (17)
C2—C1—C8—C13	−144.78 (15)	C20—C21—C22—C30	−90.84 (16)
C13—C8—C9—C10	0.0 (3)	C3—C4—O23—C24	3.2 (3)
C1—C8—C9—C10	177.73 (18)	C5—C4—O23—C24	−177.1 (2)
C8—C9—C10—C11	1.2 (3)	C6—C5—O25—C26	−87.3 (2)
C9—C10—C11—C12	−0.9 (4)	C4—C5—O25—C26	93.7 (2)
C10—C11—C12—C13	−0.7 (4)	C5—C6—O27—C28	−179.04 (18)
C10—C11—C12—C17	−179.8 (2)	C7—C6—O27—C28	1.1 (3)
C11—C12—C13—C14	−176.88 (19)	N18—C22—C30—O33	−33.4 (2)
C17—C12—C13—C14	2.3 (3)	C21—C22—C30—O33	78.6 (2)
C11—C12—C13—C8	1.8 (3)	N18—C22—C30—O31	150.80 (15)
C17—C12—C13—C8	−179.02 (18)	C21—C22—C30—O31	−97.26 (17)
C9—C8—C13—C12	−1.5 (3)	O33—C30—O31—C32	−1.0 (3)
C1—C8—C13—C12	−179.24 (15)	C22—C30—O31—C32	174.9 (2)
C9—C8—C13—C14	177.14 (17)	O41^i—O41—C43—O42	−0.6 (1)
C1—C8—C13—C14	−0.6 (3)	O41^i—O41—C43—C44	178.4 (5)

Symmetry code: (i) −x+2, −y+2, −z.

(III) '5-(3,4,5-trimethoxyphenyl)-1,2,3,5-tetrahydro-11a-naphto[1,8 − f,g] indolizine-3-one'

Crystal data

C24H23NO4	F(000) = 824
Mr = 389.43	Dx = 1.301 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 9.909 (1) Å	Cell parameters from 25 reflections
b = 8.519 (1) Å	θ = 30–42°
c = 23.793 (1) Å	µ = 0.72 mm^−1
β = 98.104 (4)°	T = 293 K
V = 1988.4 (3) Å^3	Prism, colourless
Z = 4	0.40 × 0.40 × 0.30 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3676 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.012
Graphite monochromator	θmax = 71.9°, θmin = 3.8°
θ/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.763, Tmax = 0.814	l = 0→29
5132 measured reflections	3 standard reflections every 200 reflections
3899 independent reflections	intensity decay: 7%

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)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.121	Calculated w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 0.415P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3899 reflections	Δρmax = 0.28 e Å^−3
263 parameters	Δρmin = −0.23 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0041 (4)

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
C1	0.30088 (14)	0.64693 (16)	0.35524 (5)	0.0467 (3)
H1	0.2640	0.7348	0.3749	0.056*
C2	0.26920 (14)	0.49576 (16)	0.38601 (5)	0.0476 (3)
C3	0.36764 (15)	0.38318 (17)	0.40165 (6)	0.0531 (3)
H3	0.4559	0.3975	0.3935	0.064*
C4	0.33435 (15)	0.24784 (17)	0.42978 (6)	0.0523 (3)
C5	0.20279 (15)	0.22501 (17)	0.44166 (5)	0.0506 (3)
C6	0.10484 (14)	0.34057 (18)	0.42691 (6)	0.0537 (3)
C7	0.13753 (15)	0.47525 (18)	0.39875 (6)	0.0541 (3)
H7	0.0715	0.5515	0.3884	0.065*
C8	0.45099 (14)	0.67717 (15)	0.35587 (5)	0.0465 (3)
C9	0.52774 (17)	0.74120 (18)	0.40274 (6)	0.0573 (4)
H9	0.4860	0.7677	0.4341	0.069*
C10	0.66865 (17)	0.7676 (2)	0.40429 (7)	0.0644 (4)
H10	0.7186	0.8125	0.4363	0.077*
C11	0.73144 (16)	0.72778 (19)	0.35936 (7)	0.0617 (4)
H11	0.8246	0.7451	0.3609	0.074*
C12	0.65752 (14)	0.66034 (16)	0.31017 (6)	0.0527 (3)
C13	0.72141 (16)	0.61678 (19)	0.26288 (8)	0.0630 (4)
H13	0.8149	0.6306	0.2642	0.076*
C14	0.64762 (17)	0.5550 (2)	0.21562 (7)	0.0655 (4)
H14	0.6911	0.5252	0.1851	0.079*
C15	0.50635 (16)	0.53580 (18)	0.21255 (6)	0.0571 (4)
H15	0.4571	0.4947	0.1797	0.069*
C16	0.43913 (14)	0.57643 (15)	0.25709 (5)	0.0464 (3)
C17	0.51472 (13)	0.63665 (14)	0.30778 (5)	0.0449 (3)
N18	0.23288 (11)	0.64794 (13)	0.29666 (4)	0.0461 (3)
C19	0.11433 (14)	0.72111 (17)	0.27927 (6)	0.0521 (3)
C20	0.07753 (16)	0.6911 (2)	0.21641 (7)	0.0680 (4)
H20A	0.0052	0.6140	0.2093	0.082*
H20B	0.0483	0.7872	0.1964	0.082*
C21	0.20737 (17)	0.6302 (2)	0.19813 (6)	0.0692 (5)
H21A	0.2584	0.7147	0.1837	0.083*
H21B	0.1879	0.5509	0.1688	0.083*
C22	0.28716 (14)	0.55932 (17)	0.25235 (6)	0.0495 (3)
H22	0.2635	0.4482	0.2551	0.059*
O23	0.42556 (11)	0.13133 (13)	0.44784 (5)	0.0693 (3)
C24	0.56536 (17)	0.1637 (2)	0.44757 (8)	0.0694 (5)
H24A	0.5836	0.1708	0.4091	0.104*
H24B	0.6191	0.0808	0.4667	0.104*
H24C	0.5883	0.2613	0.4667	0.104*
O25	0.17270 (11)	0.09469 (12)	0.47165 (4)	0.0601 (3)
C26	0.0977 (2)	−0.0248 (2)	0.43924 (9)	0.0844 (6)
H26A	0.0053	0.0091	0.4286	0.127*
H26B	0.0989	−0.1189	0.4615	0.127*
H26C	0.1384	−0.0454	0.4057	0.127*
O27	−0.01912 (11)	0.31089 (15)	0.44314 (6)	0.0756 (4)
C28	−0.11990 (18)	0.4293 (3)	0.43256 (10)	0.0842 (6)
H28A	−0.1982	0.4003	0.4498	0.126*
H28B	−0.1459	0.4408	0.3924	0.126*
H28C	−0.0839	0.5269	0.4483	0.126*
O29	0.04836 (11)	0.79678 (15)	0.30979 (5)	0.0690 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0566 (7)	0.0456 (7)	0.0395 (6)	0.0058 (6)	0.0118 (5)	0.0029 (5)
C2	0.0559 (7)	0.0491 (7)	0.0392 (6)	0.0038 (6)	0.0118 (5)	0.0045 (5)
C3	0.0561 (8)	0.0535 (8)	0.0526 (7)	0.0062 (6)	0.0175 (6)	0.0089 (6)
C4	0.0583 (8)	0.0492 (7)	0.0499 (7)	0.0067 (6)	0.0095 (6)	0.0082 (6)
C5	0.0592 (8)	0.0520 (7)	0.0404 (6)	−0.0037 (6)	0.0065 (5)	0.0064 (5)
C6	0.0511 (7)	0.0604 (8)	0.0506 (7)	−0.0022 (6)	0.0101 (6)	0.0062 (6)
C7	0.0542 (8)	0.0551 (8)	0.0539 (8)	0.0068 (6)	0.0105 (6)	0.0097 (6)
C8	0.0568 (7)	0.0409 (6)	0.0418 (6)	0.0029 (5)	0.0067 (5)	0.0051 (5)
C9	0.0713 (9)	0.0583 (8)	0.0413 (7)	0.0018 (7)	0.0044 (6)	0.0024 (6)
C10	0.0689 (9)	0.0648 (9)	0.0538 (8)	−0.0017 (8)	−0.0113 (7)	0.0019 (7)
C11	0.0530 (8)	0.0595 (9)	0.0693 (9)	0.0013 (7)	−0.0032 (7)	0.0069 (7)
C12	0.0516 (7)	0.0464 (7)	0.0604 (8)	0.0042 (6)	0.0085 (6)	0.0056 (6)
C13	0.0515 (8)	0.0611 (9)	0.0800 (10)	0.0055 (7)	0.0211 (7)	0.0016 (8)
C14	0.0689 (9)	0.0639 (9)	0.0695 (10)	0.0050 (8)	0.0305 (8)	−0.0063 (8)
C15	0.0653 (9)	0.0559 (8)	0.0523 (8)	0.0024 (7)	0.0163 (6)	−0.0090 (6)
C16	0.0536 (7)	0.0402 (6)	0.0466 (7)	0.0032 (5)	0.0109 (5)	0.0004 (5)
C17	0.0508 (7)	0.0388 (6)	0.0455 (7)	0.0036 (5)	0.0086 (5)	0.0044 (5)
N18	0.0502 (6)	0.0473 (6)	0.0416 (5)	0.0059 (5)	0.0096 (4)	0.0041 (4)
C19	0.0465 (7)	0.0556 (8)	0.0548 (8)	0.0025 (6)	0.0092 (6)	0.0036 (6)
C20	0.0566 (9)	0.0897 (12)	0.0551 (8)	0.0070 (8)	−0.0007 (7)	0.0006 (8)
C21	0.0667 (10)	0.0939 (12)	0.0451 (8)	0.0116 (9)	0.0017 (7)	−0.0049 (8)
C22	0.0549 (7)	0.0478 (7)	0.0463 (7)	0.0007 (6)	0.0085 (6)	−0.0049 (5)
O23	0.0631 (6)	0.0571 (6)	0.0889 (8)	0.0116 (5)	0.0153 (6)	0.0247 (6)
C24	0.0628 (9)	0.0697 (10)	0.0785 (11)	0.0176 (8)	0.0201 (8)	0.0189 (8)
O25	0.0714 (7)	0.0554 (6)	0.0520 (6)	−0.0131 (5)	0.0035 (5)	0.0115 (4)
C26	0.1153 (16)	0.0591 (10)	0.0779 (12)	−0.0171 (10)	0.0110 (11)	−0.0084 (9)
O27	0.0545 (6)	0.0757 (8)	0.1002 (9)	0.0018 (5)	0.0237 (6)	0.0258 (7)
C28	0.0529 (9)	0.0914 (13)	0.1111 (15)	0.0069 (9)	0.0215 (9)	0.0169 (12)
O29	0.0587 (6)	0.0813 (8)	0.0682 (7)	0.0199 (6)	0.0134 (5)	−0.0036 (6)

Geometric parameters (Å, º)

C1—N18	1.460 (2)	C14—H14	0.9300
C1—C8	1.508 (2)	C15—C16	1.3732 (19)
C1—C2	1.536 (2)	C15—H15	0.9300
C1—H1	0.9800	C16—C17	1.4226 (19)
C2—C3	1.3812 (19)	C16—C22	1.5013 (19)
C2—C7	1.391 (2)	N18—C19	1.343 (2)
C3—C4	1.3958 (19)	N18—C22	1.460 (2)
C3—H3	0.9300	C19—O29	1.2263 (17)
C4—O23	1.3700 (17)	C19—C20	1.511 (2)
C4—C5	1.386 (2)	C20—C21	1.507 (2)
C5—O25	1.3749 (16)	C20—H20A	0.9700
C5—C6	1.392 (2)	C20—H20B	0.9700
C6—O27	1.3622 (17)	C21—C22	1.538 (2)
C6—C7	1.390 (2)	C21—H21A	0.9700
C7—H7	0.9300	C21—H21B	0.9700
C8—C9	1.371 (2)	C22—H22	0.9800
C8—C17	1.4251 (18)	O23—C24	1.4133 (19)
C9—C10	1.410 (2)	C24—H24A	0.9600
C9—H9	0.9300	C24—H24B	0.9600
C10—C11	1.354 (2)	C24—H24C	0.9600
C10—H10	0.9300	O25—C26	1.422 (2)
C11—C12	1.412 (2)	C26—H26A	0.9600
C11—H11	0.9300	C26—H26B	0.9600
C12—C13	1.416 (2)	C26—H26C	0.9600
C12—C17	1.4225 (19)	O27—C28	1.417 (2)
C13—C14	1.358 (2)	C28—H28A	0.9600
C13—H13	0.9300	C28—H28B	0.9600
C14—C15	1.401 (2)	C28—H28C	0.9600
N18—C1—C8	109.29 (10)	C17—C16—C22	120.10 (11)
N18—C1—C2	111.24 (11)	C12—C17—C16	119.14 (12)
C8—C1—C2	113.98 (11)	C12—C17—C8	118.97 (12)
N18—C1—H1	107.3	C16—C17—C8	121.87 (12)
C8—C1—H1	107.3	C19—N18—C22	114.4 (1)
C2—C1—H1	107.3	C19—N18—C1	124.3 (1)
C3—C2—C7	120.17 (12)	C22—N18—C1	121.3 (1)
C3—C2—C1	121.78 (12)	O29—C19—N18	125.31 (13)
C7—C2—C1	118.04 (12)	O29—C19—C20	126.92 (13)
C2—C3—C4	119.81 (13)	N18—C19—C20	107.77 (12)
C2—C3—H3	120.1	C21—C20—C19	104.32 (12)
C4—C3—H3	120.1	C21—C20—H20A	110.9
O23—C4—C5	115.61 (12)	C19—C20—H20A	110.9
O23—C4—C3	123.97 (13)	C21—C20—H20B	110.9
C5—C4—C3	120.42 (13)	C19—C20—H20B	110.9
O25—C5—C4	119.87 (13)	H20A—C20—H20B	108.9
O25—C5—C6	120.49 (13)	C20—C21—C22	104.58 (12)
C4—C5—C6	119.45 (13)	C20—C21—H21A	110.8
O27—C6—C7	124.79 (14)	C22—C21—H21A	110.8
O27—C6—C5	114.94 (13)	C20—C21—H21B	110.8
C7—C6—C5	120.25 (13)	C22—C21—H21B	110.8
C6—C7—C2	119.87 (13)	H21A—C21—H21B	108.9
C6—C7—H7	120.1	N18—C22—C16	111.30 (11)
C2—C7—H7	120.1	N18—C22—C21	101.80 (11)
C9—C8—C17	119.45 (13)	C16—C22—C21	114.61 (12)
C9—C8—C1	120.61 (12)	N18—C22—H22	109.6
C17—C8—C1	119.93 (12)	C16—C22—H22	109.6
C8—C9—C10	121.22 (14)	C21—C22—H22	109.6
C8—C9—H9	119.4	C4—O23—C24	117.46 (12)
C10—C9—H9	119.4	O23—C24—H24A	109.5
C11—C10—C9	120.22 (14)	O23—C24—H24B	109.5
C11—C10—H10	119.9	H24A—C24—H24B	109.5
C9—C10—H10	119.9	O23—C24—H24C	109.5
C10—C11—C12	120.93 (14)	H24A—C24—H24C	109.5
C10—C11—H11	119.5	H24B—C24—H24C	109.5
C12—C11—H11	119.5	C5—O25—C26	115.57 (12)
C11—C12—C13	121.83 (14)	O25—C26—H26A	109.5
C11—C12—C17	119.18 (13)	O25—C26—H26B	109.5
C13—C12—C17	118.99 (14)	H26A—C26—H26B	109.5
C14—C13—C12	120.71 (14)	O25—C26—H26C	109.5
C14—C13—H13	119.6	H26A—C26—H26C	109.5
C12—C13—H13	119.6	H26B—C26—H26C	109.5
C13—C14—C15	120.38 (14)	C6—O27—C28	117.31 (13)
C13—C14—H14	119.8	O27—C28—H28A	109.5
C15—C14—H14	119.8	O27—C28—H28B	109.5
C16—C15—C14	121.34 (14)	H28A—C28—H28B	109.5
C16—C15—H15	119.3	O27—C28—H28C	109.5
C14—C15—H15	119.3	H28A—C28—H28C	109.5
C15—C16—C17	119.37 (13)	H28B—C28—H28C	109.5
C15—C16—C22	120.53 (13)
N18—C1—C2—C3	110.99 (14)	C11—C12—C17—C8	−1.95 (19)
C8—C1—C2—C3	−13.1 (2)	C13—C12—C17—C8	178.59 (13)
N18—C1—C2—C7	−69.92 (15)	C15—C16—C17—C12	2.93 (19)
C8—C1—C2—C7	165.97 (12)	C22—C16—C17—C12	−176.42 (12)
C7—C2—C3—C4	0.7 (2)	C15—C16—C17—C8	−178.45 (13)
C1—C2—C3—C4	179.73 (13)	C22—C16—C17—C8	2.20 (19)
C2—C3—C4—O23	−178.75 (14)	C9—C8—C17—C12	1.47 (19)
C2—C3—C4—C5	0.6 (2)	C1—C8—C17—C12	−177.48 (11)
O23—C4—C5—O25	2.3 (2)	C9—C8—C17—C16	−177.15 (12)
C3—C4—C5—O25	−177.06 (13)	C1—C8—C17—C16	3.90 (18)
O23—C4—C5—C6	177.38 (13)	C8—C1—N18—C19	−135.55 (13)
C3—C4—C5—C6	−2.0 (2)	C2—C1—N18—C19	97.7 (2)
O25—C5—C6—O27	−1.6 (2)	C8—C1—N18—C22	48.05 (16)
C4—C5—C6—O27	−176.57 (13)	C2—C1—N18—C22	−78.67 (15)
O25—C5—C6—C7	177.22 (13)	C22—N18—C19—O29	177.06 (14)
C4—C5—C6—C7	2.2 (2)	C1—N18—C19—O29	0.4 (2)
O27—C6—C7—C2	177.68 (14)	C22—N18—C19—C20	−2.17 (17)
C5—C6—C7—C2	−1.0 (2)	C1—N18—C19—C20	−178.79 (13)
C3—C2—C7—C6	−0.5 (2)	O29—C19—C20—C21	165.91 (16)
C1—C2—C7—C6	−179.57 (13)	N18—C19—C20—C21	−14.87 (19)
N18—C1—C8—C9	154.66 (12)	C19—C20—C21—C22	24.96 (19)
C2—C1—C8—C9	−80.19 (16)	C19—N18—C22—C16	140.30 (12)
N18—C1—C8—C17	−26.4 (2)	C1—N18—C22—C16	−42.97 (16)
C2—C1—C8—C17	98.75 (14)	C19—N18—C22—C21	17.74 (16)
C17—C8—C9—C10	−0.1 (2)	C1—N18—C22—C21	−165.52 (13)
C1—C8—C9—C10	178.89 (13)	C15—C16—C22—N18	−164.01 (13)
C8—C9—C10—C11	−0.9 (2)	C17—C16—C22—N18	15.33 (17)
C9—C10—C11—C12	0.4 (2)	C15—C16—C22—C21	−49.16 (18)
C10—C11—C12—C13	−179.53 (15)	C17—C16—C22—C21	130.18 (14)
C10—C11—C12—C17	1.0 (2)	C20—C21—C22—N18	−25.57 (17)
C11—C12—C13—C14	−178.69 (15)	C20—C21—C22—C16	−145.83 (14)
C17—C12—C13—C14	0.8 (2)	C5—C4—O23—C24	−167.0 (1)
C12—C13—C14—C15	1.1 (3)	C3—C4—O23—C24	12.4 (2)
C13—C14—C15—C16	−0.9 (3)	C4—C5—O25—C26	−105.53 (17)
C14—C15—C16—C17	−1.1 (2)	C6—C5—O25—C26	79.5 (2)
C14—C15—C16—C22	178.22 (14)	C7—C6—O27—C28	−2.8 (2)
C11—C12—C17—C16	176.71 (12)	C5—C6—O27—C28	175.9 (2)
C13—C12—C17—C16	−2.75 (19)

(IV) '5-(3,4,5-trimethoxyphenyl)-1,2,3,5,12,12a-hexahydronaphto[1,2-f] indolizine-3,12-dione'

Crystal data

C25H23NO5	F(000) = 880
Mr = 417.44	Dx = 1.318 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
a = 10.868 (1) Å	Cell parameters from 25 reflections
b = 12.937 (1) Å	θ = 30–42°
c = 15.049 (1) Å	µ = 0.75 mm^−1
β = 96.009 (4)°	T = 293 K
V = 2104.3 (3) Å^3	Prism, colourless
Z = 4	0.30 × 0.30 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 71.9°, θmin = 4.1°
θ/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.806, Tmax = 0.896	l = −18→18
7065 measured reflections	3 standard reflections every 200 reflections
4129 independent reflections	intensity decay: 2%

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.118	Calculated w = 1/[σ^2(Fo^2) + (0.0553P)^2 + 0.3806P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
4129 reflections	Δρmax = 0.16 e Å^−3
281 parameters	Δρmin = −0.15 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0046 (4)

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
C1	0.42719 (12)	0.90831 (11)	0.81740 (8)	0.0479 (3)
H1	0.4379	0.9825	0.8074	0.057*
C2	0.31903 (12)	0.87173 (10)	0.75149 (8)	0.0456 (3)
C3	0.22877 (12)	0.80541 (11)	0.77628 (9)	0.0495 (3)
H3	0.2326	0.7808	0.8346	0.059*
C4	0.13196 (12)	0.77580 (11)	0.71325 (9)	0.0506 (3)
C5	0.12764 (13)	0.81096 (11)	0.62567 (9)	0.0507 (3)
C6	0.22167 (13)	0.87423 (11)	0.60071 (9)	0.0513 (3)
C7	0.31600 (13)	0.90613 (11)	0.66393 (9)	0.0503 (3)
H7	0.3772	0.9505	0.6477	0.060*
C8	0.40822 (11)	0.89417 (10)	0.91479 (8)	0.0433 (3)
C9	0.47678 (12)	0.82360 (10)	0.96819 (9)	0.0507 (3)
C10	0.45762 (15)	0.81305 (12)	1.05963 (10)	0.0622 (4)
H10	0.5061	0.7670	1.0955	0.075*
C11	0.37031 (16)	0.86874 (14)	1.09522 (10)	0.0639 (4)
H11	0.3584	0.8599	1.1550	0.077*
C12	0.29693 (13)	0.94025 (12)	1.04284 (9)	0.0547 (3)
C13	0.20173 (16)	0.99815 (16)	1.07787 (12)	0.0739 (5)
H13	0.1868	0.9886	1.1370	0.089*
C14	0.13236 (17)	1.06710 (16)	1.02647 (14)	0.0821 (6)
H14	0.0703	1.1039	1.0505	0.099*
C15	0.15359 (16)	1.08294 (14)	0.93830 (13)	0.0754 (5)
H15	0.1064	1.1312	0.9039	0.090*
C16	0.24259 (14)	1.02868 (12)	0.90171 (10)	0.0585 (4)
H16	0.2551	1.0402	0.8423	0.070*
C17	0.31686 (12)	0.95498 (10)	0.95199 (8)	0.0465 (3)
N18	0.54063 (11)	0.85722 (12)	0.79817 (8)	0.0623 (3)
C19	0.62303 (16)	0.8982 (2)	0.74767 (12)	0.0831 (6)
C20	0.72249 (18)	0.8175 (3)	0.73974 (16)	0.1158 (11)
H20A	0.7180	0.7912	0.6791	0.139*
H20B	0.8039	0.8470	0.7552	0.139*
C21	0.6988 (2)	0.7325 (3)	0.8034 (2)	0.1232 (10)
H21A	0.7611	0.7329	0.8545	0.148*
H21B	0.7003	0.6658	0.7742	0.148*
C22	0.57020 (15)	0.75420 (15)	0.83269 (12)	0.0737 (5)
H22	0.5103	0.7042	0.8049	0.088*
O23	0.03700 (10)	0.71249 (10)	0.73114 (7)	0.0697 (3)
C24	0.04707 (19)	0.66037 (19)	0.81349 (13)	0.0953 (7)
H24A	−0.0224	0.6150	0.8156	0.143*
H24B	0.0484	0.7098	0.8612	0.143*
H24C	0.1222	0.6208	0.8200	0.143*
O25	0.03340 (10)	0.77949 (9)	0.56347 (7)	0.0649 (3)
C26	−0.06010 (15)	0.85514 (17)	0.54464 (12)	0.0785 (5)
H26A	−0.0285	0.9108	0.5114	0.118*
H26B	−0.0851	0.8814	0.5997	0.118*
H26C	−0.1300	0.8245	0.5101	0.118*
O27	0.21305 (10)	0.89955 (10)	0.51252 (6)	0.0699 (3)
C28	0.31589 (17)	0.95003 (14)	0.48092 (11)	0.0712 (5)
H28A	0.3032	0.9553	0.4170	0.107*
H28B	0.3897	0.9109	0.4980	0.107*
H28C	0.3244	1.0180	0.5064	0.107*
O29	0.61511 (13)	0.98403 (17)	0.71401 (8)	0.1016 (6)
C30	0.56690 (14)	0.75422 (12)	0.93196 (12)	0.0645 (4)
O31	0.63351 (13)	0.69718 (11)	0.97990 (11)	0.0990 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0434 (6)	0.0538 (7)	0.0446 (7)	−0.0048 (6)	−0.0034 (5)	−0.0002 (6)
C2	0.0438 (6)	0.0489 (7)	0.0423 (6)	−0.0014 (5)	−0.0038 (5)	−0.0015 (5)
C3	0.0485 (7)	0.0578 (8)	0.0404 (6)	−0.0041 (6)	−0.0035 (5)	0.0046 (5)
C4	0.0457 (7)	0.0548 (8)	0.0496 (7)	−0.0075 (6)	−0.0031 (5)	0.0047 (6)
C5	0.0492 (7)	0.0543 (8)	0.0455 (7)	−0.0076 (6)	−0.0098 (5)	0.0017 (6)
C6	0.0551 (8)	0.0561 (8)	0.0406 (6)	−0.0065 (6)	−0.0046 (5)	0.0050 (6)
C7	0.0496 (7)	0.0537 (8)	0.0461 (7)	−0.0089 (6)	−0.0016 (5)	0.0032 (6)
C8	0.0421 (6)	0.0428 (6)	0.0426 (6)	−0.0047 (5)	−0.0071 (5)	0.0000 (5)
C9	0.0461 (7)	0.0474 (7)	0.0550 (7)	−0.0029 (6)	−0.0119 (6)	0.0020 (6)
C10	0.0656 (9)	0.0604 (9)	0.0555 (8)	−0.0048 (7)	−0.0175 (7)	0.0167 (7)
C11	0.0716 (10)	0.0752 (10)	0.0430 (7)	−0.0148 (8)	−0.0030 (7)	0.0074 (7)
C12	0.0544 (8)	0.0611 (8)	0.0473 (7)	−0.0112 (6)	−0.0007 (6)	−0.0064 (6)
C13	0.0664 (10)	0.0953 (13)	0.0611 (9)	−0.0099 (9)	0.0117 (8)	−0.0228 (9)
C14	0.0615 (10)	0.0919 (13)	0.0922 (13)	0.0116 (9)	0.0047 (9)	−0.0329 (11)
C15	0.0676 (10)	0.0677 (10)	0.0870 (12)	0.0180 (8)	−0.0095 (9)	−0.0122 (9)
C16	0.0602 (8)	0.0543 (8)	0.0585 (8)	0.0079 (7)	−0.0053 (6)	−0.0004 (6)
C17	0.0465 (7)	0.0464 (7)	0.0448 (6)	−0.0038 (5)	−0.0041 (5)	−0.0019 (5)
N18	0.0426 (6)	0.0877 (10)	0.0557 (7)	−0.0026 (6)	0.0005 (5)	−0.0123 (6)
C19	0.0561 (9)	0.147 (2)	0.0458 (9)	−0.0226 (11)	0.0057 (7)	−0.0229 (11)
C20	0.0511 (10)	0.208 (3)	0.0884 (15)	−0.0024 (14)	0.0105 (10)	−0.0686 (18)
C21	0.0790 (15)	0.176 (3)	0.1153 (19)	0.0428 (17)	0.0143 (14)	−0.045 (2)
C22	0.0527 (8)	0.0777 (11)	0.0872 (12)	0.0121 (8)	−0.0099 (8)	−0.0282 (9)
O23	0.0582 (6)	0.0880 (8)	0.0596 (6)	−0.0276 (6)	−0.0098 (5)	0.0191 (5)
C24	0.0804 (12)	0.1260 (18)	0.0767 (12)	−0.0401 (12)	−0.0055 (9)	0.0415 (12)
O25	0.0619 (6)	0.0701 (7)	0.0571 (6)	−0.0173 (5)	−0.0205 (5)	0.0064 (5)
C26	0.0529 (9)	0.1060 (14)	0.0722 (11)	−0.0048 (9)	−0.0144 (8)	0.0115 (10)
O27	0.0725 (7)	0.0914 (8)	0.0429 (5)	−0.0253 (6)	−0.0086 (5)	0.0148 (5)
C28	0.0828 (11)	0.0782 (11)	0.0523 (8)	−0.0189 (9)	0.0048 (8)	0.0128 (8)
O29	0.0836 (9)	0.1678 (17)	0.0551 (7)	−0.0390 (10)	0.0156 (6)	0.0038 (9)
C30	0.0492 (8)	0.0537 (8)	0.0864 (11)	0.0044 (7)	−0.0126 (7)	−0.0029 (8)
O31	0.0815 (9)	0.0854 (9)	0.1251 (12)	0.0344 (7)	−0.0134 (8)	0.0168 (8)

Geometric parameters (Å, º)

C1—N18	1.454 (2)	C15—C16	1.358 (2)
C1—C8	1.512 (2)	C15—H15	0.9300
C1—C2	1.533 (2)	C16—C17	1.4160 (19)
C1—H1	0.9800	C16—H16	0.9300
C2—C3	1.3835 (19)	N18—C19	1.343 (2)
C2—C7	1.3879 (18)	N18—C22	1.454 (2)
C3—C4	1.3945 (18)	C19—O29	1.220 (3)
C3—H3	0.9300	C19—C20	1.517 (3)
C4—O23	1.3663 (16)	C20—C21	1.497 (4)
C4—C5	1.3903 (18)	C20—H20A	0.9700
C5—O25	1.3748 (15)	C20—H20B	0.9700
C5—C6	1.391 (2)	C21—C22	1.535 (3)
C6—O27	1.3606 (16)	C21—H21A	0.9700
C6—C7	1.3864 (18)	C21—H21B	0.9700
C7—H7	0.9300	C22—C30	1.498 (2)
C8—C9	1.3818 (18)	C22—H22	0.9800
C8—C17	1.4265 (18)	O23—C24	1.405 (2)
C9—C10	1.420 (2)	C24—H24A	0.9600
C9—C30	1.475 (2)	C24—H24B	0.9600
C10—C11	1.346 (2)	C24—H24C	0.9600
C10—H10	0.9300	O25—C26	1.418 (2)
C11—C12	1.408 (2)	C26—H26A	0.9600
C11—H11	0.9300	C26—H26B	0.9600
C12—C17	1.4194 (19)	C26—H26C	0.9600
C12—C13	1.423 (2)	O27—C28	1.4188 (19)
C13—C14	1.357 (3)	C28—H28A	0.9600
C13—H13	0.9300	C28—H28B	0.9600
C14—C15	1.386 (3)	C28—H28C	0.9600
C14—H14	0.9300	C30—O31	1.2165 (19)
N18—C1—C8	110.02 (11)	C16—C17—C12	117.99 (13)
N18—C1—C2	109.87 (11)	C16—C17—C8	122.88 (12)
C8—C1—C2	114.65 (11)	C12—C17—C8	119.12 (12)
N18—C1—H1	107.3	C19—N18—C22	115.4 (2)
C8—C1—H1	107.3	C19—N18—C1	124.3 (2)
C2—C1—H1	107.3	C22—N18—C1	120.4 (1)
C3—C2—C7	120.52 (11)	O29—C19—N18	124.9 (2)
C3—C2—C1	122.33 (11)	O29—C19—C20	127.9 (2)
C7—C2—C1	117.14 (12)	N18—C19—C20	107.2 (2)
C2—C3—C4	119.52 (12)	C21—C20—C19	106.47 (18)
C2—C3—H3	120.2	C21—C20—H20A	110.4
C4—C3—H3	120.2	C19—C20—H20A	110.4
O23—C4—C5	115.58 (11)	C21—C20—H20B	110.4
O23—C4—C3	124.21 (12)	C19—C20—H20B	110.4
C5—C4—C3	120.21 (12)	H20A—C20—H20B	108.6
O25—C5—C4	119.82 (12)	C20—C21—C22	105.8 (2)
O25—C5—C6	120.42 (12)	C20—C21—H21A	110.6
C4—C5—C6	119.70 (11)	C22—C21—H21A	110.6
O27—C6—C7	124.62 (13)	C20—C21—H21B	110.6
O27—C6—C5	115.30 (11)	C22—C21—H21B	110.6
C7—C6—C5	120.07 (12)	H21A—C21—H21B	108.7
C6—C7—C2	119.90 (12)	N18—C22—C30	109.18 (13)
C6—C7—H7	120.1	N18—C22—C21	103.8 (2)
C2—C7—H7	120.1	C30—C22—C21	113.84 (16)
C9—C8—C17	119.42 (12)	N18—C22—H22	109.9
C9—C8—C1	121.58 (12)	C30—C22—H22	109.9
C17—C8—C1	119.00 (11)	C21—C22—H22	109.9
C8—C9—C10	120.16 (13)	C4—O23—C24	118.10 (12)
C8—C9—C30	121.71 (13)	O23—C24—H24A	109.5
C10—C9—C30	118.06 (13)	O23—C24—H24B	109.5
C11—C10—C9	121.00 (13)	H24A—C24—H24B	109.5
C11—C10—H10	119.5	O23—C24—H24C	109.5
C9—C10—H10	119.5	H24A—C24—H24C	109.5
C10—C11—C12	120.70 (14)	H24B—C24—H24C	109.5
C10—C11—H11	119.6	C5—O25—C26	113.51 (13)
C12—C11—H11	119.6	O25—C26—H26A	109.5
C11—C12—C17	119.53 (14)	O25—C26—H26B	109.5
C11—C12—C13	122.01 (15)	H26A—C26—H26B	109.5
C17—C12—C13	118.46 (14)	O25—C26—H26C	109.5
C14—C13—C12	121.15 (16)	H26A—C26—H26C	109.5
C14—C13—H13	119.4	H26B—C26—H26C	109.5
C12—C13—H13	119.4	C6—O27—C28	117.48 (11)
C13—C14—C15	120.33 (16)	O27—C28—H28A	109.5
C13—C14—H14	119.8	O27—C28—H28B	109.5
C15—C14—H14	119.8	H28A—C28—H28B	109.5
C16—C15—C14	120.60 (16)	O27—C28—H28C	109.5
C16—C15—H15	119.7	H28A—C28—H28C	109.5
C14—C15—H15	119.7	H28B—C28—H28C	109.5
C15—C16—C17	121.46 (15)	O31—C30—C9	121.80 (17)
C15—C16—H16	119.3	O31—C30—C22	121.09 (16)
C17—C16—H16	119.3	C9—C30—C22	117.07 (13)
N18—C1—C2—C3	106.81 (15)	C11—C12—C17—C16	−179.06 (13)
C8—C1—C2—C3	−17.7 (2)	C13—C12—C17—C16	1.5 (2)
N18—C1—C2—C7	−71.76 (16)	C11—C12—C17—C8	2.17 (19)
C8—C1—C2—C7	163.75 (12)	C13—C12—C17—C8	−177.23 (13)
C7—C2—C3—C4	−2.1 (2)	C9—C8—C17—C16	−179.81 (13)
C1—C2—C3—C4	179.37 (13)	C1—C8—C17—C16	−0.10 (19)
C2—C3—C4—O23	−178.62 (13)	C9—C8—C17—C12	−1.10 (18)
C2—C3—C4—C5	1.3 (2)	C1—C8—C17—C12	178.61 (11)
O23—C4—C5—O25	−1.5 (2)	C8—C1—N18—C19	−137.25 (14)
C3—C4—C5—O25	178.51 (13)	C2—C1—N18—C19	95.6 (2)
O23—C4—C5—C6	−178.76 (13)	C8—C1—N18—C22	44.05 (16)
C3—C4—C5—C6	1.3 (2)	C2—C1—N18—C22	−83.08 (15)
O25—C5—C6—O27	−1.0 (2)	C22—N18—C19—O29	−178.91 (16)
C4—C5—C6—O27	176.25 (14)	C1—N18—C19—O29	2.3 (3)
O25—C5—C6—C7	179.63 (14)	C22—N18—C19—C20	2.36 (18)
C4—C5—C6—C7	−3.1 (2)	C1—N18—C19—C20	−176.39 (13)
O27—C6—C7—C2	−176.93 (14)	O29—C19—C20—C21	172.3 (2)
C5—C6—C7—C2	2.4 (2)	N18—C19—C20—C21	−9.0 (2)
C3—C2—C7—C6	0.2 (2)	C19—C20—C21—C22	11.7 (2)
C1—C2—C7—C6	178.83 (13)	C19—N18—C22—C30	126.76 (14)
N18—C1—C8—C9	−12.8 (2)	C1—N18—C22—C30	−54.44 (17)
C2—C1—C8—C9	111.58 (14)	C19—N18—C22—C21	5.0 (2)
N18—C1—C8—C17	167.46 (11)	C1—N18—C22—C21	−176.19 (14)
C2—C1—C8—C17	−68.12 (16)	C20—C21—C22—N18	−10.2 (2)
C17—C8—C9—C10	−1.00 (19)	C20—C21—C22—C30	−128.8 (2)
C1—C8—C9—C10	179.30 (12)	C5—C4—O23—C24	169.2 (2)
C17—C8—C9—C30	176.15 (12)	C3—C4—O23—C24	−10.8 (2)
C1—C8—C9—C30	−3.55 (19)	C4—C5—O25—C26	102.29 (16)
C8—C9—C10—C11	2.1 (2)	C6—C5—O25—C26	−80.5 (2)
C30—C9—C10—C11	−175.14 (14)	C7—C6—O27—C28	9.0 (2)
C9—C10—C11—C12	−1.0 (2)	C5—C6—O27—C28	−170.34 (14)
C10—C11—C12—C17	−1.1 (2)	C8—C9—C30—O31	174.76 (15)
C10—C11—C12—C13	178.25 (15)	C10—C9—C30—O31	−8.0 (2)
C11—C12—C13—C14	179.67 (16)	C8—C9—C30—C22	−7.3 (2)
C17—C12—C13—C14	−1.0 (2)	C10—C9—C30—C22	169.95 (14)
C12—C13—C14—C15	−0.3 (3)	N18—C22—C30—O31	−149.06 (16)
C13—C14—C15—C16	1.0 (3)	C21—C22—C30—O31	−33.6 (3)
C14—C15—C16—C17	−0.4 (3)	N18—C22—C30—C9	32.93 (19)
C15—C16—C17—C12	−0.9 (2)	C21—C22—C30—C9	148.4 (2)
C15—C16—C17—C8	177.80 (14)