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In the syn- and anticlinal isomers of the title compound, C22H18N2O6, the indole moiety is not completely planar, with the pyrrolidine ring being distorted very slightly towards a conformation intermediate between half-chair and envelope. The molecular and packing structures in the crystals of these isomers are stabilized by C—H...O interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101020820/na1545sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101020820/na1545Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101020820/na1545IIsup3.hkl
Contains datablock II

CCDC references: 182010; 182011

Comment top

1H-Indole-2,3-dione (isatin) derivatives having acetyl substituent are of interest due to their biological activities (Bieck et al., 1993) and their use as synthetic precursors (Popp, 1975). The photoreactions of 1-acetylisatin with alkenes are one of the synthetic routes to spiroxetane derivatives (Xue et al., 2000, 2001), in which asymmetric alkenes give syn- and anti-spiroxetane isomers as a mixture separable by column chromatography. With our on-going research on the regioselectivity of the photoreactions of 1-acetylisatin and the stereochemical properties of the products, we have isolated the title compounds, (I) and (II), which were obtained from the irradiation of 1-acetylisatin with 1-acetyl-3-acetyloxyindole in benzene solution. The crystal structure determinations of (I) and (II) were undertaken in order to elucidate their conformation and to determine their steric configurations.

The crystal structure analyses of the title compounds show (I) to be the synclinal and (II) to be the anticlinal isomer. These isomers refer to the relative configuration between the isatin (C1–C8/N2) and indole (C9–C16/N1) moieties.

The bond lengths and angles in (I) and (II) are within normal ranges (Allen et al., 1987). In compound (I), the bond lenghts and angles within the isatin and indole moieties are comparable. The oxetane ring (O6/C7/C16/C9) is not planar, with a dihedral angle of 166.6 (3)° between the O6/C7/C9 and C7/C16/C9 planes. Atoms C7, C9 and C16 are the chiral centers. However, since both compounds (I) and (II) do not crystallize in a chiral space group, each structure contains molecules having opposite chirality.

Though the isatin moiety is almost planar due to the conjugation of the N—C and CO bonds, the indole moiety is not completely coplanar with the pyrrolidine ring (N1/C9/C16/C15,C10) of the indole moiety, showing a slight puckering towards a conformation intermediate between half-chair and envelope (Duax et al., 1976). The puckering amplitude Q2 is 0.075 (3) Å and the local pseudo-twofold axis and pseudo-mirror contains atoms C15 and C9, respectively. The dihedral angle between the pyrrolidine and benzene rings in the indole is 3.3 (2)°.

The mean planes through the isatin and indole moieties make dihedral angles of 89.1 (1) and 65.4 (1)°, respectively, with the oxetane ring; the two moieties make a dihedral angle of 53.3 (1)° with one another. The acetyl groups attached at atoms N1 and N2 make angles of 4.1 (2) and 7.5 (2) Å, respectively, with the isatin and indole moiety. The acetyloxy substituent forms a plane and makes an angle of 67.8 (1)° with the indole moiety.

In compound (II), there are two crystallographic independent molecules in the asymmetric unit. The bond lengths, angles and chirality of molecules A and B agree with one another. The bond lengths and angles within the two molecules are comparable with those of (I), albeit with a different configuration.

In molecules A and B, the oxetane ring is not planar, with dihedral angles between the O6/C7/C9 and C7/C16/C9 planes of 166.0 (4)° in molecule A and 166.6 (4)° in molecule B. In Fig. 2, atom C7 is the R chiral center and atoms C9 and C16 are the S chiral centers. The isatin moiety is also planar in both molecules A and B, whereas the indole moiety is not planar. The pyrrolidine ring of the indole moiety is also in a conformation intermediate between half-chair and envelope, with the puckering amplitude Q2 = 0.080 (4) Å and the local pseudo-twofold axis and pseudo-mirror containing atoms C15 and C9, respectively, in both molecules. The dihedral angle between the pyrrolidine and benzene rings in the indole moiety is 4.1 (2) and 3.9 (2)° in molecules A and B, respectively.

In molecules A and B, the mean planes through the isatin and indole moieties make average dihedral angles of 89.6 (4) and 65.7 (3)°, respectively, with the oxetane ring. The average dihedral angle between the isatin and indole moieties is 43.4 (4)°.

The acetyl group attached at atom N2 makes an angle of 6.3 (4)°, on average, with the isatin moiety for both molecules, while that attached at atom N1 is twisted at an angle of 5.5 (4)° in molecule A and 4.3 (3)° in molecule B with respect to their indole planes. The plane passing through the acetyloxy group attached at atom C16 make an average dihedral angle of 64.9 (4)° with the indole plane.

The relative conformation about the bond joining the isatin and indole moieties of isomers (I) and (II) is defined by the C6—C7—C16—C15 torsion angle of -27.4 (4)° in (I), and 145.0 (4)° in molecules A and B of (II). These indicate that (I) is (-)synclinal, and that molecules A and B of (II) are (-)anticlinal.

In the structure of (I), there is one intramolecular interaction (C14—H14···O4) and two weak intermolecular interactions (C18—H18B···O4 and C20—H20B···O1; Table 2) interconnecting molecular columns stacked along the b axis into a three-dimensional network. In the structure of (II), there is also a weak intramolecular interaction (C14—H14···O4) in molecules A and B. Molecules A and B are interconnected by intermolecular C—H···O interactions (Table 4) into a three-dimensional molecular arrangement. These weak C—H···O interactions, together with van der Waals and dipole—dipole interactions, stabilize the molecular and packing structure in the two crystals.

Experimental top

A solution of 1-acetylisatin (0.05 M) in the presence of an excess amount of 1-acetyl-3-acetyloxyindole in benzene was irradiated using light having λ >= 400 nm. Upon completion of the reaction, the solvent was removed in vacuo and the residue was separated by flash chromatography on a silica-gel column using petroleum ether–ethyl acetate as eluent to afford compounds (I) and (II). Single crystals suitable for X-ray diffraction were obtained by recrystallization from an acetone–petroleum ether mixture.

Refinement top

H atoms were fixed and geometrically were treated as riding on their parent C atoms, with aromatic C—H distances in the range 0.93–0.98 Å. Due to the absence of any significant anomalous scatters in compound (II), the 3301 Friedel equivalents were merged before the final refinements. The choice of the absolute structure was chosen arbitrarily.

Computing details top

For both compounds, data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. The structure of (II) showing 40% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 3] Fig. 3. Packing diagram of (I) viewed down the b axis.
[Figure 4] Fig. 4. Packing diagram of (II) viewed down the b axis.
(I) syn-2a'-acetoxy-1,7'-diacetyl-7',7a'-dihydro-2-oxo- spiro[1H-indole-3(2H),2'(2a'H)oxeto[2,3-b]indole] top
Crystal data top
C22H18N2O6F(000) = 424
Mr = 406.38Dx = 1.446 Mg m3
Triclinic, P1Melting point: 466K K
a = 8.9350 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.1189 (3) ÅCell parameters from 4055 reflections
c = 13.4690 (6) Åθ = 2.6–28.3°
α = 75.897 (1)°µ = 0.11 mm1
β = 89.831 (1)°T = 183 K
γ = 62.201 (1)°Block, colorless
V = 933.64 (7) Å30.38 × 0.32 × 0.20 mm
Z = 2
Data collection top
Siemens SMART CCD area-detector
diffractometer
3160 independent reflections
Radiation source: fine-focus sealed tube2252 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.6°
ω scansh = 1010
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.961, Tmax = 0.979l = 1015
4475 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.194 w = 1/[σ2(Fo2) + (0.0848P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max < 0.001
3160 reflectionsΔρmax = 0.56 e Å3
275 parametersΔρmin = 0.52 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.058 (9)
Crystal data top
C22H18N2O6γ = 62.201 (1)°
Mr = 406.38V = 933.64 (7) Å3
Triclinic, P1Z = 2
a = 8.9350 (4) ÅMo Kα radiation
b = 9.1189 (3) ŵ = 0.11 mm1
c = 13.4690 (6) ÅT = 183 K
α = 75.897 (1)°0.38 × 0.32 × 0.20 mm
β = 89.831 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
3160 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2252 reflections with I > 2σ(I)
Tmin = 0.961, Tmax = 0.979Rint = 0.078
4475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.194H-atom parameters constrained
S = 0.95Δρmax = 0.56 e Å3
3160 reflectionsΔρmin = 0.52 e Å3
275 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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.

Due to the large fraction of weak data at higher angles, the 2θ maximum was limited to 50° for the two compounds.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.1379 (4)0.7573 (3)1.08829 (19)0.0412 (7)
O20.8978 (3)0.7172 (3)0.54551 (17)0.0278 (6)
O30.2881 (2)1.0966 (2)0.69147 (15)0.0169 (5)
O40.0809 (3)1.0288 (3)0.73625 (17)0.0241 (6)
O50.3895 (3)0.9935 (3)0.91094 (16)0.0257 (6)
O60.6206 (3)0.7322 (3)0.81079 (15)0.0208 (5)
N10.6700 (3)0.8093 (3)0.63396 (18)0.0177 (6)
N20.2905 (3)0.7927 (3)0.95855 (18)0.0161 (6)
C10.3036 (4)0.6539 (4)0.9193 (2)0.0162 (7)
C20.2490 (4)0.5349 (4)0.9572 (2)0.0232 (7)
H20.18900.54001.01390.028*
C30.2872 (4)0.4061 (4)0.9074 (2)0.0266 (8)
H30.25250.32370.93190.032*
C40.3750 (4)0.3980 (4)0.8227 (3)0.0249 (8)
H40.39810.31150.79070.030*
C50.4288 (4)0.5192 (4)0.7852 (2)0.0204 (7)
H50.48880.51400.72850.025*
C60.3918 (4)0.6479 (4)0.8335 (2)0.0163 (7)
C70.4389 (4)0.7880 (3)0.8115 (2)0.0143 (7)
C80.3714 (4)0.8752 (4)0.8985 (2)0.0159 (7)
C90.5905 (4)0.8711 (4)0.7195 (2)0.0151 (6)
H90.60960.96230.73290.018*
C100.5508 (4)0.7916 (4)0.5736 (2)0.0181 (7)
C110.5790 (4)0.7196 (4)0.4914 (2)0.0232 (7)
H110.68540.67430.46840.028*
C120.4408 (4)0.7178 (4)0.4446 (2)0.0259 (8)
H120.45610.67070.38910.031*
C130.2816 (4)0.7841 (4)0.4783 (2)0.0270 (8)
H130.19220.78110.44540.032*
C140.2553 (4)0.8552 (4)0.5617 (2)0.0205 (7)
H140.14870.90100.58430.025*
C150.3922 (4)0.8562 (3)0.6102 (2)0.0149 (7)
C160.4024 (4)0.9181 (3)0.7024 (2)0.0139 (6)
C170.8376 (4)0.7622 (4)0.6211 (2)0.0188 (7)
C180.9392 (4)0.7675 (4)0.7075 (3)0.0265 (8)
H18A0.91370.71840.77250.040*
H18B0.91020.88480.70210.040*
H18C1.05870.70250.70310.040*
C190.1236 (4)1.1386 (4)0.7090 (2)0.0181 (7)
C200.0160 (4)1.3268 (4)0.6926 (2)0.0245 (8)
H20A0.07851.37080.72220.037*
H20B0.08541.34870.72490.037*
H20C0.01491.38270.61990.037*
C210.2090 (4)0.8345 (4)1.0465 (2)0.0231 (8)
C220.2167 (5)0.9747 (5)1.0823 (3)0.0331 (9)
H22A0.15501.08251.03040.050*
H22B0.33360.94831.09430.050*
H22C0.16660.98291.14520.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0612 (19)0.0541 (17)0.0320 (15)0.0426 (15)0.0334 (13)0.0209 (13)
O20.0253 (13)0.0294 (12)0.0259 (13)0.0099 (11)0.0144 (10)0.0097 (10)
O30.0203 (12)0.0129 (10)0.0178 (11)0.0083 (9)0.0059 (8)0.0042 (8)
O40.0251 (13)0.0237 (12)0.0273 (13)0.0139 (11)0.0100 (9)0.0090 (10)
O50.0407 (15)0.0309 (13)0.0180 (12)0.0252 (12)0.0092 (10)0.0110 (10)
O60.0188 (12)0.0257 (11)0.0144 (11)0.0098 (10)0.0029 (8)0.0016 (9)
N10.0209 (14)0.0228 (13)0.0136 (13)0.0129 (12)0.0071 (10)0.0073 (11)
N20.0195 (14)0.0203 (13)0.0103 (13)0.0106 (11)0.0055 (10)0.0049 (10)
C10.0193 (16)0.0183 (14)0.0095 (15)0.0091 (13)0.0005 (11)0.0011 (12)
C20.0269 (18)0.0236 (16)0.0183 (17)0.0139 (15)0.0036 (13)0.0005 (13)
C30.039 (2)0.0221 (16)0.0218 (18)0.0203 (16)0.0001 (14)0.0015 (14)
C40.0299 (19)0.0159 (15)0.0274 (19)0.0095 (14)0.0004 (14)0.0065 (14)
C50.0227 (17)0.0165 (15)0.0179 (16)0.0061 (13)0.0022 (12)0.0048 (13)
C60.0209 (16)0.0158 (14)0.0111 (15)0.0093 (13)0.0006 (11)0.0005 (12)
C70.0157 (16)0.0164 (14)0.0108 (15)0.0078 (13)0.0030 (11)0.0032 (12)
C80.0199 (17)0.0205 (15)0.0115 (15)0.0122 (13)0.0033 (11)0.0061 (12)
C90.0184 (16)0.0212 (15)0.0115 (15)0.0130 (13)0.0075 (11)0.0067 (12)
C100.0257 (17)0.0174 (15)0.0130 (15)0.0131 (14)0.0031 (12)0.0014 (12)
C110.035 (2)0.0235 (16)0.0164 (17)0.0177 (15)0.0112 (13)0.0067 (13)
C120.041 (2)0.0267 (17)0.0165 (17)0.0193 (16)0.0079 (14)0.0117 (14)
C130.037 (2)0.0311 (18)0.0205 (18)0.0211 (16)0.0006 (14)0.0090 (14)
C140.0252 (18)0.0242 (16)0.0163 (16)0.0153 (14)0.0039 (12)0.0052 (13)
C150.0229 (16)0.0137 (14)0.0083 (15)0.0101 (13)0.0034 (11)0.0004 (11)
C160.0156 (15)0.0109 (13)0.0162 (16)0.0072 (12)0.0045 (11)0.0040 (12)
C170.0209 (17)0.0141 (15)0.0198 (17)0.0090 (13)0.0074 (12)0.0006 (12)
C180.0215 (18)0.0305 (18)0.0286 (19)0.0129 (15)0.0061 (13)0.0091 (15)
C190.0165 (16)0.0204 (15)0.0141 (16)0.0062 (14)0.0022 (11)0.0049 (12)
C200.0228 (18)0.0189 (16)0.0260 (18)0.0056 (14)0.0081 (13)0.0054 (14)
C210.0256 (18)0.0255 (17)0.0130 (16)0.0075 (15)0.0070 (13)0.0064 (13)
C220.039 (2)0.044 (2)0.027 (2)0.0222 (18)0.0178 (15)0.0242 (17)
Geometric parameters (Å, º) top
O1—C211.200 (4)C7—C161.571 (4)
O2—C171.220 (4)C9—C161.531 (4)
O3—C191.371 (4)C9—H90.9800
O3—C161.432 (3)C10—C111.385 (4)
O4—C191.207 (4)C10—C151.399 (4)
O5—C81.212 (3)C11—C121.396 (5)
O6—C91.454 (3)C11—H110.9300
O6—C71.459 (3)C12—C131.387 (5)
N1—C171.376 (4)C12—H120.9300
N1—C101.432 (4)C13—C141.395 (4)
N1—C91.445 (4)C13—H130.9300
N2—C81.396 (4)C14—C151.394 (4)
N2—C211.426 (4)C14—H140.9300
N2—C11.443 (4)C15—C161.502 (4)
C1—C21.378 (4)C17—C181.502 (4)
C1—C61.394 (4)C18—H18A0.9600
C2—C31.398 (4)C18—H18B0.9600
C2—H20.9300C18—H18C0.9600
C3—C41.379 (5)C19—C201.482 (4)
C3—H30.9300C20—H20A0.9600
C4—C51.389 (5)C20—H20B0.9600
C4—H40.9300C20—H20C0.9600
C5—C61.385 (4)C21—C221.502 (4)
C5—H50.9300C22—H22A0.9600
C6—C71.488 (4)C22—H22B0.9600
C7—C81.540 (4)C22—H22C0.9600
C19—O3—C16116.4 (2)C12—C11—H11121.4
C9—O6—C792.63 (19)C13—C12—C11122.1 (3)
C17—N1—C10127.4 (3)C13—C12—H12118.9
C17—N1—C9123.9 (2)C11—C12—H12118.9
C10—N1—C9108.5 (2)C12—C13—C14120.1 (3)
C8—N2—C21126.2 (2)C12—C13—H13119.9
C8—N2—C1109.6 (2)C14—C13—H13119.9
C21—N2—C1124.2 (3)C15—C14—C13118.6 (3)
C2—C1—C6121.3 (3)C15—C14—H14120.7
C2—C1—N2129.3 (3)C13—C14—H14120.7
C6—C1—N2109.4 (3)C14—C15—C10120.2 (3)
C1—C2—C3117.6 (3)C14—C15—C16130.1 (3)
C1—C2—H2121.2C10—C15—C16109.7 (3)
C3—C2—H2121.2O3—C16—C15115.1 (2)
C4—C3—C2121.7 (3)O3—C16—C9113.2 (2)
C4—C3—H3119.1C15—C16—C9103.3 (2)
C2—C3—H3119.1O3—C16—C7117.7 (2)
C3—C4—C5120.0 (3)C15—C16—C7116.9 (2)
C3—C4—H4120.0C9—C16—C785.5 (2)
C5—C4—H4120.0O2—C17—N1121.7 (3)
C6—C5—C4119.1 (3)O2—C17—C18123.3 (3)
C6—C5—H5120.5N1—C17—C18114.9 (3)
C4—C5—H5120.5C17—C18—H18A109.5
C5—C6—C1120.3 (3)C17—C18—H18B109.5
C5—C6—C7129.8 (3)H18A—C18—H18B109.5
C1—C6—C7109.8 (3)C17—C18—H18C109.5
O6—C7—C6115.6 (2)H18A—C18—H18C109.5
O6—C7—C8110.7 (2)H18B—C18—H18C109.5
C6—C7—C8103.2 (2)O4—C19—O3121.2 (3)
O6—C7—C1689.3 (2)O4—C19—C20127.2 (3)
C6—C7—C16124.0 (2)O3—C19—C20111.6 (3)
C8—C7—C16114.0 (2)C19—C20—H20A109.5
O5—C8—N2127.6 (3)C19—C20—H20B109.5
O5—C8—C7124.4 (3)H20A—C20—H20B109.5
N2—C8—C7108.0 (2)C19—C20—H20C109.5
N1—C9—O6112.8 (2)H20A—C20—H20C109.5
N1—C9—C16107.6 (2)H20B—C20—H20C109.5
O6—C9—C1691.0 (2)O1—C21—N2119.1 (3)
N1—C9—H9114.4O1—C21—C22123.0 (3)
O6—C9—H9114.4N2—C21—C22117.8 (3)
C16—C9—H9114.4C21—C22—H22A109.5
C11—C10—C15121.8 (3)C21—C22—H22B109.5
C11—C10—N1128.0 (3)H22A—C22—H22B109.5
C15—C10—N1110.2 (3)C21—C22—H22C109.5
C10—C11—C12117.1 (3)H22A—C22—H22C109.5
C10—C11—H11121.4H22B—C22—H22C109.5
C8—N2—C1—C2176.9 (3)N1—C10—C11—C12179.9 (3)
C21—N2—C1—C22.2 (5)C10—C11—C12—C130.3 (5)
C8—N2—C1—C60.5 (3)C11—C12—C13—C140.1 (5)
C21—N2—C1—C6179.5 (3)C12—C13—C14—C150.7 (5)
C6—C1—C2—C30.8 (4)C13—C14—C15—C101.9 (4)
N2—C1—C2—C3176.2 (3)C13—C14—C15—C16177.8 (3)
C1—C2—C3—C40.5 (5)C11—C10—C15—C142.4 (4)
C2—C3—C4—C50.4 (5)N1—C10—C15—C14178.8 (2)
C3—C4—C5—C60.5 (5)C11—C10—C15—C16177.3 (3)
C4—C5—C6—C10.8 (4)N1—C10—C15—C161.4 (3)
C4—C5—C6—C7177.7 (3)C19—O3—C16—C1581.8 (3)
C2—C1—C6—C51.0 (4)C19—O3—C16—C9159.7 (2)
N2—C1—C6—C5176.6 (2)C19—O3—C16—C762.3 (3)
C2—C1—C6—C7178.5 (3)C14—C15—C16—O359.9 (4)
N2—C1—C6—C70.9 (3)C10—C15—C16—O3120.4 (3)
C9—O6—C7—C6137.6 (2)C14—C15—C16—C9176.3 (3)
C9—O6—C7—C8105.7 (2)C10—C15—C16—C93.5 (3)
C9—O6—C7—C169.70 (19)C14—C15—C16—C784.6 (4)
C5—C6—C7—O654.5 (4)C10—C15—C16—C795.2 (3)
C1—C6—C7—O6122.6 (3)N1—C9—C16—O3118.1 (2)
C5—C6—C7—C8175.4 (3)O6—C9—C16—O3127.6 (2)
C1—C6—C7—C81.7 (3)N1—C9—C16—C157.0 (3)
C5—C6—C7—C1653.2 (4)O6—C9—C16—C15107.3 (2)
C1—C6—C7—C16129.6 (3)N1—C9—C16—C7123.6 (2)
C21—N2—C8—O51.4 (5)O6—C9—C16—C79.26 (18)
C1—N2—C8—O5177.6 (3)O6—C7—C16—O3123.1 (2)
C21—N2—C8—C7179.4 (3)C6—C7—C16—O3116.1 (3)
C1—N2—C8—C71.6 (3)C8—C7—C16—O310.8 (3)
O6—C7—C8—O553.1 (4)O6—C7—C16—C1593.4 (3)
C6—C7—C8—O5177.2 (3)C6—C7—C16—C1527.4 (4)
C16—C7—C8—O545.7 (4)C8—C7—C16—C15154.2 (2)
O6—C7—C8—N2126.2 (2)O6—C7—C16—C99.22 (18)
C6—C7—C8—N22.0 (3)C6—C7—C16—C9130.0 (3)
C16—C7—C8—N2135.1 (2)C8—C7—C16—C9103.1 (2)
C17—N1—C9—O684.1 (3)C10—N1—C17—O29.3 (5)
C10—N1—C9—O690.6 (3)C9—N1—C17—O2177.0 (3)
C17—N1—C9—C16177.1 (2)C10—N1—C17—C18169.6 (3)
C10—N1—C9—C168.2 (3)C9—N1—C17—C184.1 (4)
C7—O6—C9—N1119.6 (2)C16—O3—C19—O42.9 (4)
C7—O6—C9—C1610.0 (2)C16—O3—C19—C20178.3 (2)
C17—N1—C10—C111.9 (5)C8—N2—C21—O1176.8 (3)
C9—N1—C10—C11172.6 (3)C1—N2—C21—O14.3 (5)
C17—N1—C10—C15179.4 (3)C8—N2—C21—C223.2 (4)
C9—N1—C10—C156.1 (3)C1—N2—C21—C22175.7 (3)
C15—C10—C11—C121.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O40.932.533.155 (4)125
C18—H18B···O4i0.962.543.271 (6)133
C20—H20B···O1ii0.962.593.323 (4)133
Symmetry codes: (i) x+1, y, z; (ii) x, y+2, z+2.
(II) anti-2a'-acetoxy-1,7'-diacetyl-7',7a'-dihydro-2-oxo- spiro[1H-indole-3(2H),2'(2a'H)oxeto[2,3-b]indole] top
Crystal data top
C22H18N2O6Dx = 1.409 Mg m3
Mr = 406.38Melting point: 476K K
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
a = 14.5310 (2) ÅCell parameters from 8192 reflections
b = 8.7676 (1) Åθ = 2.7–28.4°
c = 30.0679 (1) ŵ = 0.10 mm1
V = 3830.71 (7) Å3T = 183 K
Z = 8Block, colorless
F(000) = 16960.50 × 0.30 × 0.22 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3370 independent reflections
Radiation source: fine-focus sealed tube2679 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 2.7°
ω scansh = 1617
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1010
Tmin = 0.950, Tmax = 0.978l = 2635
17100 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.115 w = 1/[σ2(Fo2) + (0.0607P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
3370 reflectionsΔρmax = 0.35 e Å3
547 parametersΔρmin = 0.36 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0061 (7)
Crystal data top
C22H18N2O6V = 3830.71 (7) Å3
Mr = 406.38Z = 8
Orthorhombic, Pna21Mo Kα radiation
a = 14.5310 (2) ŵ = 0.10 mm1
b = 8.7676 (1) ÅT = 183 K
c = 30.0679 (1) Å0.50 × 0.30 × 0.22 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3370 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
2679 reflections with I > 2σ(I)
Tmin = 0.950, Tmax = 0.978Rint = 0.095
17100 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0481 restraint
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.35 e Å3
3370 reflectionsΔρmin = 0.36 e Å3
547 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1A0.7304 (3)0.6188 (4)0.14474 (12)0.0458 (10)
O2A0.7143 (2)0.6640 (4)0.46003 (11)0.0415 (9)
O3A0.81028 (19)0.2835 (4)0.32003 (11)0.0216 (7)
O4A0.8687 (2)0.3511 (4)0.25386 (11)0.0327 (8)
O5A0.7188 (3)0.7506 (4)0.27846 (18)0.0421 (13)
O6A0.63362 (18)0.5079 (4)0.32948 (10)0.0263 (7)
N1A0.7295 (2)0.5437 (4)0.39408 (12)0.0237 (8)
N2A0.7076 (2)0.5785 (4)0.21867 (12)0.0260 (9)
C1A0.6739 (3)0.4266 (5)0.21550 (14)0.0220 (10)
C2A0.6525 (3)0.3414 (6)0.17825 (16)0.0304 (12)
H2A0.66160.37990.14980.037*
C3A0.6169 (3)0.1970 (7)0.18490 (18)0.0334 (13)
H3A0.60260.13770.16020.040*
C4A0.6018 (3)0.1378 (6)0.22639 (16)0.0304 (11)
H4A0.57660.04090.22950.037*
C5A0.6245 (3)0.2233 (6)0.26400 (19)0.0255 (12)
H5A0.61570.18420.29240.031*
C6A0.6603 (3)0.3668 (5)0.25788 (14)0.0219 (10)
C7A0.6925 (3)0.4793 (5)0.29180 (15)0.0217 (10)
C8A0.7088 (3)0.6241 (6)0.26397 (15)0.0268 (11)
C9A0.6984 (3)0.4401 (5)0.36058 (13)0.0193 (10)
H9A0.67970.34000.37190.023*
C10A0.8103 (3)0.6195 (5)0.37807 (15)0.0253 (10)
C11A0.8587 (4)0.7380 (6)0.3974 (2)0.0353 (16)
H11A0.84160.77820.42490.042*
C12A0.9334 (4)0.7939 (7)0.3743 (2)0.0419 (14)
H12A0.96610.87490.38660.050*
C13A0.9615 (4)0.7368 (6)0.3346 (3)0.0384 (18)
H13A1.01250.77830.32030.046*
C14A0.9139 (3)0.6163 (5)0.31553 (17)0.0317 (12)
H14A0.93250.57580.28840.038*
C15A0.8380 (3)0.5571 (5)0.33765 (14)0.0211 (10)
C16A0.7722 (3)0.4340 (5)0.32429 (14)0.0195 (9)
C17A0.6873 (3)0.5665 (6)0.43408 (16)0.0288 (11)
C18A0.6062 (3)0.4671 (6)0.44511 (16)0.0367 (13)
H18A0.56920.45310.41900.055*
H18B0.57000.51500.46790.055*
H18C0.62750.36980.45550.055*
C19A0.8589 (3)0.2562 (5)0.2826 (2)0.0264 (15)
C20A0.8977 (4)0.0982 (6)0.2829 (2)0.0442 (14)
H20A0.87940.04710.30980.066*
H20B0.96360.10310.28160.066*
H20C0.87490.04280.25770.066*
C21A0.7357 (3)0.6703 (7)0.1820 (2)0.0368 (14)
C22A0.7711 (5)0.8254 (7)0.1917 (2)0.063 (2)
H22A0.72200.88760.20310.095*
H22B0.79490.87010.16500.095*
H22C0.81920.81880.21350.095*
O1B0.5337 (3)1.1281 (4)0.67895 (12)0.0512 (11)
O2B0.5442 (3)1.1664 (4)0.36560 (11)0.0427 (10)
O3B0.44771 (19)0.7850 (4)0.50565 (11)0.0229 (7)
O4B0.3893 (2)0.8503 (4)0.57205 (11)0.0315 (8)
O5B0.5423 (3)1.2516 (4)0.54575 (16)0.0401 (13)
O6B0.62566 (18)1.0055 (4)0.49494 (10)0.0270 (7)
N1B0.5274 (2)1.0434 (4)0.43059 (11)0.0218 (8)
N2B0.5526 (2)1.0838 (4)0.60538 (12)0.0243 (9)
C1B0.5861 (3)0.9297 (5)0.60915 (15)0.0213 (10)
C2B0.6071 (3)0.8478 (6)0.64700 (17)0.0288 (12)
H2B0.59780.88810.67530.035*
C3B0.6430 (3)0.7019 (7)0.64092 (17)0.0321 (12)
H3B0.65760.64380.66580.038*
C4B0.6577 (3)0.6407 (6)0.59931 (17)0.0327 (11)
H4B0.68300.54380.59640.039*
C5B0.6345 (3)0.7242 (6)0.56168 (19)0.0263 (12)
H5B0.64310.68350.53340.032*
C6B0.5987 (3)0.8679 (5)0.56695 (14)0.0202 (9)
C7B0.5669 (3)0.9804 (5)0.53342 (13)0.0207 (10)
C8B0.5511 (3)1.1245 (5)0.56037 (16)0.0255 (10)
C9B0.5594 (3)0.9381 (5)0.46465 (14)0.0212 (10)
H9B0.57700.83750.45330.025*
C10B0.4477 (3)1.1196 (5)0.44709 (15)0.0239 (10)
C11B0.3995 (4)1.2400 (5)0.4274 (2)0.0345 (16)
H11B0.41691.28000.40000.041*
C12B0.3242 (4)1.2972 (7)0.4506 (2)0.0430 (14)
H12B0.29101.37790.43860.052*
C13B0.2973 (4)1.2370 (6)0.4914 (3)0.0408 (19)
H13B0.24681.27760.50620.049*
C14B0.3454 (3)1.1171 (5)0.50984 (16)0.0292 (11)
H14B0.32741.07630.53700.035*
C15B0.4205 (3)1.0583 (5)0.48757 (14)0.0223 (10)
C16B0.4865 (3)0.9341 (5)0.50064 (14)0.0185 (9)
C17B0.5714 (3)1.0663 (6)0.39114 (15)0.0278 (11)
C18B0.6518 (3)0.9683 (6)0.38024 (17)0.0373 (13)
H18E0.67740.92770.40720.056*
H18D0.69751.02790.36510.056*
H18F0.63230.88600.36140.056*
C19B0.3977 (3)0.7564 (5)0.5435 (2)0.0245 (14)
C20B0.3605 (4)0.5996 (6)0.54192 (18)0.0389 (13)
H20F0.40980.52880.53700.058*
H20D0.31670.59180.51810.058*
H20E0.33070.57650.56960.058*
C21B0.5279 (3)1.1763 (6)0.64151 (18)0.0333 (12)
C22B0.4918 (4)1.3324 (6)0.6317 (2)0.0465 (16)
H22D0.43901.32460.61260.070*
H22E0.53871.39140.61720.070*
H22F0.47441.38140.65900.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.053 (2)0.058 (3)0.027 (2)0.0041 (19)0.0058 (17)0.0168 (19)
O2A0.057 (2)0.044 (2)0.0231 (19)0.0061 (18)0.0035 (17)0.0125 (17)
O3A0.0253 (15)0.0221 (16)0.0175 (18)0.0043 (14)0.0032 (14)0.0012 (16)
O4A0.0328 (18)0.048 (2)0.0174 (18)0.0034 (16)0.0070 (15)0.0053 (16)
O5A0.063 (3)0.020 (3)0.043 (3)0.0025 (16)0.013 (2)0.0004 (15)
O6A0.0201 (14)0.041 (2)0.0183 (16)0.0061 (14)0.0013 (13)0.0023 (15)
N1A0.0276 (19)0.028 (2)0.015 (2)0.0017 (16)0.0021 (16)0.0007 (16)
N2A0.032 (2)0.028 (2)0.018 (2)0.0033 (17)0.0002 (17)0.0069 (17)
C1A0.020 (2)0.030 (3)0.016 (2)0.0037 (19)0.0014 (18)0.0037 (19)
C2A0.033 (3)0.042 (3)0.016 (3)0.003 (2)0.001 (2)0.002 (2)
C3A0.033 (3)0.052 (4)0.015 (3)0.006 (3)0.008 (2)0.005 (3)
C4A0.030 (2)0.030 (3)0.031 (3)0.005 (2)0.001 (2)0.003 (2)
C5A0.028 (2)0.032 (3)0.017 (3)0.001 (2)0.000 (2)0.002 (2)
C6A0.019 (2)0.031 (3)0.015 (2)0.0004 (19)0.0016 (18)0.001 (2)
C7A0.021 (2)0.028 (3)0.016 (2)0.0002 (19)0.0005 (18)0.0015 (19)
C8A0.031 (2)0.029 (3)0.021 (3)0.005 (2)0.004 (2)0.003 (2)
C9A0.026 (2)0.023 (3)0.009 (2)0.0002 (19)0.0003 (17)0.0011 (17)
C10A0.025 (2)0.023 (3)0.028 (3)0.0013 (19)0.0063 (19)0.001 (2)
C11A0.040 (3)0.035 (4)0.030 (4)0.001 (2)0.019 (3)0.005 (2)
C12A0.039 (3)0.032 (3)0.054 (4)0.007 (3)0.022 (3)0.008 (3)
C13A0.027 (3)0.030 (4)0.058 (5)0.008 (2)0.006 (3)0.014 (3)
C14A0.025 (2)0.032 (3)0.037 (3)0.001 (2)0.001 (2)0.009 (2)
C15A0.020 (2)0.022 (2)0.021 (2)0.0016 (18)0.0021 (18)0.0033 (19)
C16A0.024 (2)0.021 (2)0.013 (2)0.0027 (18)0.0007 (18)0.0008 (18)
C17A0.033 (2)0.035 (3)0.018 (2)0.013 (2)0.000 (2)0.001 (2)
C18A0.038 (3)0.051 (4)0.021 (3)0.011 (2)0.006 (2)0.002 (2)
C19A0.023 (3)0.037 (4)0.019 (4)0.0029 (19)0.001 (2)0.006 (2)
C20A0.048 (3)0.039 (3)0.045 (3)0.015 (2)0.003 (3)0.006 (3)
C21A0.033 (3)0.040 (4)0.037 (3)0.011 (2)0.006 (3)0.021 (3)
C22A0.087 (5)0.033 (4)0.070 (5)0.001 (3)0.039 (4)0.013 (3)
O1B0.085 (3)0.045 (2)0.023 (2)0.005 (2)0.017 (2)0.0062 (17)
O2B0.059 (2)0.046 (3)0.024 (2)0.0088 (18)0.0019 (17)0.0173 (18)
O3B0.0261 (16)0.0289 (17)0.0137 (18)0.0044 (14)0.0014 (14)0.0018 (17)
O4B0.0297 (17)0.044 (2)0.0208 (19)0.0069 (15)0.0049 (14)0.0009 (16)
O5B0.060 (2)0.028 (3)0.032 (3)0.0061 (16)0.011 (2)0.0041 (15)
O6B0.0230 (15)0.044 (2)0.0144 (15)0.0061 (14)0.0025 (13)0.0072 (14)
N1B0.0288 (19)0.025 (2)0.0117 (19)0.0006 (16)0.0008 (16)0.0053 (16)
N2B0.0281 (19)0.024 (2)0.020 (2)0.0037 (16)0.0019 (17)0.0023 (17)
C1B0.020 (2)0.026 (3)0.018 (2)0.0019 (18)0.0043 (18)0.0003 (19)
C2B0.031 (2)0.040 (3)0.015 (3)0.008 (2)0.007 (2)0.001 (2)
C3B0.034 (3)0.034 (3)0.028 (3)0.001 (2)0.006 (2)0.014 (3)
C4B0.036 (3)0.033 (3)0.029 (3)0.005 (2)0.002 (2)0.009 (2)
C5B0.024 (2)0.035 (3)0.021 (3)0.002 (2)0.002 (2)0.002 (2)
C6B0.021 (2)0.025 (3)0.014 (2)0.0045 (19)0.0023 (18)0.001 (2)
C7B0.021 (2)0.028 (3)0.013 (2)0.0059 (19)0.0015 (17)0.0047 (18)
C8B0.026 (2)0.024 (3)0.026 (3)0.0058 (19)0.007 (2)0.004 (2)
C9B0.021 (2)0.025 (3)0.017 (2)0.0004 (19)0.0014 (18)0.0061 (19)
C10B0.029 (2)0.021 (3)0.021 (2)0.0032 (19)0.0077 (19)0.0008 (19)
C11B0.044 (3)0.023 (3)0.036 (4)0.002 (2)0.013 (3)0.004 (2)
C12B0.044 (3)0.026 (3)0.059 (4)0.013 (3)0.018 (3)0.001 (3)
C13B0.029 (3)0.040 (4)0.053 (5)0.010 (2)0.008 (3)0.008 (3)
C14B0.027 (2)0.034 (3)0.027 (3)0.001 (2)0.002 (2)0.004 (2)
C15B0.024 (2)0.024 (3)0.019 (2)0.0017 (18)0.0062 (18)0.0031 (19)
C16B0.022 (2)0.021 (2)0.012 (2)0.0021 (17)0.0006 (18)0.0013 (17)
C17B0.035 (2)0.035 (3)0.013 (2)0.013 (2)0.003 (2)0.001 (2)
C18B0.042 (3)0.047 (4)0.023 (3)0.008 (3)0.010 (2)0.001 (3)
C19B0.022 (2)0.037 (4)0.014 (3)0.0053 (19)0.002 (2)0.004 (2)
C20B0.047 (3)0.040 (3)0.030 (3)0.015 (2)0.004 (2)0.008 (2)
C21B0.035 (3)0.035 (3)0.030 (3)0.010 (2)0.011 (2)0.006 (2)
C22B0.050 (3)0.041 (4)0.048 (4)0.011 (3)0.004 (3)0.015 (3)
Geometric parameters (Å, º) top
O1A—C21A1.210 (7)O1B—C21B1.205 (7)
O2A—C17A1.222 (6)O2B—C17B1.231 (6)
O3A—C19A1.350 (7)O3B—C19B1.374 (6)
O3A—C16A1.436 (5)O3B—C16B1.431 (5)
O4A—C19A1.209 (7)O4B—C19B1.196 (6)
O5A—C8A1.200 (6)O5B—C8B1.205 (6)
O6A—C7A1.442 (5)O6B—C9B1.452 (5)
O6A—C9A1.453 (5)O6B—C7B1.455 (5)
N1A—C17A1.365 (6)N1B—C17B1.363 (6)
N1A—C9A1.430 (5)N1B—C10B1.426 (6)
N1A—C10A1.433 (6)N1B—C9B1.455 (5)
N2A—C8A1.420 (6)N2B—C8B1.400 (6)
N2A—C1A1.422 (6)N2B—C21B1.402 (6)
N2A—C21A1.426 (7)N2B—C1B1.441 (6)
C1A—C2A1.382 (6)C1B—C2B1.380 (7)
C1A—C6A1.392 (6)C1B—C6B1.392 (6)
C2A—C3A1.382 (8)C2B—C3B1.393 (8)
C2A—H2A0.9300C2B—H2B0.9300
C3A—C4A1.369 (7)C3B—C4B1.378 (7)
C3A—H3A0.9300C3B—H3B0.9300
C4A—C5A1.396 (7)C4B—C5B1.390 (7)
C4A—H4A0.9300C4B—H4B0.9300
C5A—C6A1.374 (7)C5B—C6B1.372 (7)
C5A—H5A0.9300C5B—H5B0.9300
C6A—C7A1.494 (6)C6B—C7B1.485 (6)
C7A—C8A1.539 (6)C7B—C8B1.518 (7)
C7A—C16A1.567 (6)C7B—C16B1.581 (6)
C9A—C16A1.531 (6)C9B—C16B1.515 (6)
C9A—H9A0.9800C9B—H9B0.9800
C10A—C11A1.383 (7)C10B—C15B1.388 (6)
C10A—C15A1.392 (6)C10B—C11B1.399 (7)
C11A—C12A1.379 (8)C11B—C12B1.392 (8)
C11A—H11A0.9300C11B—H11B0.9300
C12A—C13A1.358 (10)C12B—C13B1.389 (10)
C12A—H12A0.9300C12B—H12B0.9300
C13A—C14A1.387 (8)C13B—C14B1.379 (7)
C13A—H13A0.9300C13B—H13B0.9300
C14A—C15A1.389 (6)C14B—C15B1.381 (6)
C14A—H14A0.9300C14B—H14B0.9300
C15A—C16A1.497 (6)C15B—C16B1.503 (6)
C17A—C18A1.503 (7)C17B—C18B1.486 (7)
C18A—H18A0.9600C18B—H18E0.9600
C18A—H18B0.9600C18B—H18D0.9600
C18A—H18C0.9600C18B—H18F0.9600
C19A—C20A1.496 (7)C19B—C20B1.478 (7)
C20A—H20A0.9600C20B—H20F0.9600
C20A—H20B0.9600C20B—H20D0.9600
C20A—H20C0.9600C20B—H20E0.9600
C21A—C22A1.483 (9)C21B—C22B1.495 (8)
C22A—H22A0.9600C22B—H22D0.9600
C22A—H22B0.9600C22B—H22E0.9600
C22A—H22C0.9600C22B—H22F0.9600
C19A—O3A—C16A116.1 (4)C19B—O3B—C16B117.5 (4)
C7A—O6A—C9A92.9 (3)C9B—O6B—C7B92.7 (3)
C17A—N1A—C9A124.9 (4)C17B—N1B—C10B127.9 (4)
C17A—N1A—C10A126.6 (4)C17B—N1B—C9B123.8 (4)
C9A—N1A—C10A108.5 (3)C10B—N1B—C9B108.2 (3)
C8A—N2A—C1A109.4 (3)C8B—N2B—C21B126.7 (4)
C8A—N2A—C21A125.5 (4)C8B—N2B—C1B108.7 (3)
C1A—N2A—C21A125.1 (4)C21B—N2B—C1B124.6 (4)
C2A—C1A—C6A120.5 (4)C2B—C1B—C6B121.4 (4)
C2A—C1A—N2A129.6 (4)C2B—C1B—N2B128.9 (4)
C6A—C1A—N2A109.9 (4)C6B—C1B—N2B109.7 (4)
C1A—C2A—C3A117.5 (5)C1B—C2B—C3B116.9 (5)
C1A—C2A—H2A121.2C1B—C2B—H2B121.6
C3A—C2A—H2A121.2C3B—C2B—H2B121.6
C4A—C3A—C2A122.6 (5)C4B—C3B—C2B122.3 (5)
C4A—C3A—H3A118.7C4B—C3B—H3B118.8
C2A—C3A—H3A118.7C2B—C3B—H3B118.8
C3A—C4A—C5A119.8 (5)C3B—C4B—C5B119.7 (5)
C3A—C4A—H4A120.1C3B—C4B—H4B120.1
C5A—C4A—H4A120.1C5B—C4B—H4B120.1
C6A—C5A—C4A118.2 (5)C6B—C5B—C4B118.8 (5)
C6A—C5A—H5A120.9C6B—C5B—H5B120.6
C4A—C5A—H5A120.9C4B—C5B—H5B120.6
C5A—C6A—C1A121.4 (4)C5B—C6B—C1B120.8 (4)
C5A—C6A—C7A129.2 (4)C5B—C6B—C7B130.5 (5)
C1A—C6A—C7A109.4 (4)C1B—C6B—C7B108.6 (4)
O6A—C7A—C6A117.7 (3)O6B—C7B—C6B117.2 (3)
O6A—C7A—C8A112.1 (4)O6B—C7B—C8B112.8 (3)
C6A—C7A—C8A102.8 (4)C6B—C7B—C8B103.7 (4)
O6A—C7A—C16A89.6 (3)O6B—C7B—C16B88.7 (3)
C6A—C7A—C16A119.3 (4)C6B—C7B—C16B118.9 (4)
C8A—C7A—C16A115.8 (3)C8B—C7B—C16B115.8 (3)
O5A—C8A—N2A127.6 (5)O5B—C8B—N2B126.2 (5)
O5A—C8A—C7A125.7 (5)O5B—C8B—C7B126.2 (5)
N2A—C8A—C7A106.7 (4)N2B—C8B—C7B107.6 (4)
N1A—C9A—O6A113.5 (4)O6B—C9B—N1B113.3 (4)
N1A—C9A—C16A107.6 (3)O6B—C9B—C16B91.4 (3)
O6A—C9A—C16A90.6 (3)N1B—C9B—C16B107.1 (3)
N1A—C9A—H9A114.3O6B—C9B—H9B114.2
O6A—C9A—H9A114.3N1B—C9B—H9B114.2
C16A—C9A—H9A114.3C16B—C9B—H9B114.2
C11A—C10A—C15A121.1 (5)C15B—C10B—C11B121.4 (5)
C11A—C10A—N1A128.6 (5)C15B—C10B—N1B110.8 (4)
C15A—C10A—N1A110.3 (4)C11B—C10B—N1B127.8 (5)
C12A—C11A—C10A117.0 (6)C12B—C11B—C10B117.0 (6)
C12A—C11A—H11A121.5C12B—C11B—H11B121.5
C10A—C11A—H11A121.5C10B—C11B—H11B121.5
C13A—C12A—C11A123.3 (6)C13B—C12B—C11B121.8 (5)
C13A—C12A—H12A118.3C13B—C12B—H12B119.1
C11A—C12A—H12A118.3C11B—C12B—H12B119.1
C12A—C13A—C14A119.6 (5)C14B—C13B—C12B120.2 (5)
C12A—C13A—H13A120.2C14B—C13B—H13B119.9
C14A—C13A—H13A120.2C12B—C13B—H13B119.9
C13A—C14A—C15A118.9 (5)C13B—C14B—C15B119.3 (5)
C13A—C14A—H14A120.6C13B—C14B—H14B120.3
C15A—C14A—H14A120.6C15B—C14B—H14B120.3
C14A—C15A—C10A120.0 (4)C14B—C15B—C10B120.4 (4)
C14A—C15A—C16A130.4 (4)C14B—C15B—C16B130.4 (4)
C10A—C15A—C16A109.5 (4)C10B—C15B—C16B109.2 (4)
O3A—C16A—C15A116.2 (3)O3B—C16B—C15B116.0 (3)
O3A—C16A—C9A111.4 (3)O3B—C16B—C9B111.8 (3)
C15A—C16A—C9A103.4 (3)C15B—C16B—C9B104.0 (3)
O3A—C16A—C7A117.5 (4)O3B—C16B—C7B117.4 (3)
C15A—C16A—C7A117.2 (3)C15B—C16B—C7B116.6 (3)
C9A—C16A—C7A85.2 (3)C9B—C16B—C7B85.6 (3)
O2A—C17A—N1A121.4 (5)O2B—C17B—N1B119.9 (4)
O2A—C17A—C18A121.1 (5)O2B—C17B—C18B121.8 (4)
N1A—C17A—C18A117.5 (4)N1B—C17B—C18B118.4 (4)
C17A—C18A—H18A109.5C17B—C18B—H18E109.5
C17A—C18A—H18B109.5C17B—C18B—H18D109.5
H18A—C18A—H18B109.5H18E—C18B—H18D109.5
C17A—C18A—H18C109.5C17B—C18B—H18F109.5
H18A—C18A—H18C109.5H18E—C18B—H18F109.5
H18B—C18A—H18C109.5H18D—C18B—H18F109.5
O4A—C19A—O3A122.4 (4)O4B—C19B—O3B121.5 (4)
O4A—C19A—C20A126.7 (5)O4B—C19B—C20B128.8 (5)
O3A—C19A—C20A110.9 (5)O3B—C19B—C20B109.7 (5)
C19A—C20A—H20A109.5C19B—C20B—H20F109.5
C19A—C20A—H20B109.5C19B—C20B—H20D109.5
H20A—C20A—H20B109.5H20F—C20B—H20D109.5
C19A—C20A—H20C109.5C19B—C20B—H20E109.5
H20A—C20A—H20C109.5H20F—C20B—H20E109.5
H20B—C20A—H20C109.5H20D—C20B—H20E109.5
O1A—C21A—N2A119.2 (5)O1B—C21B—N2B120.2 (5)
O1A—C21A—C22A123.2 (5)O1B—C21B—C22B122.0 (5)
N2A—C21A—C22A117.6 (5)N2B—C21B—C22B117.8 (5)
C21A—C22A—H22A109.5C21B—C22B—H22D109.5
C21A—C22A—H22B109.5C21B—C22B—H22E109.5
H22A—C22A—H22B109.5H22D—C22B—H22E109.5
C21A—C22A—H22C109.5C21B—C22B—H22F109.5
H22A—C22A—H22C109.5H22D—C22B—H22F109.5
H22B—C22A—H22C109.5H22E—C22B—H22F109.5
C8A—N2A—C1A—C2A172.9 (4)C8B—N2B—C1B—C2B173.3 (4)
C21A—N2A—C1A—C2A7.1 (7)C21B—N2B—C1B—C2B5.5 (7)
C8A—N2A—C1A—C6A5.0 (5)C8B—N2B—C1B—C6B4.8 (5)
C21A—N2A—C1A—C6A175.0 (4)C21B—N2B—C1B—C6B176.4 (4)
C6A—C1A—C2A—C3A0.4 (7)C6B—C1B—C2B—C3B1.1 (6)
N2A—C1A—C2A—C3A177.3 (4)N2B—C1B—C2B—C3B176.8 (4)
C1A—C2A—C3A—C4A0.6 (8)C1B—C2B—C3B—C4B0.3 (7)
C2A—C3A—C4A—C5A1.4 (8)C2B—C3B—C4B—C5B1.4 (8)
C3A—C4A—C5A—C6A1.0 (7)C3B—C4B—C5B—C6B1.1 (7)
C4A—C5A—C6A—C1A0.0 (6)C4B—C5B—C6B—C1B0.4 (7)
C4A—C5A—C6A—C7A178.1 (4)C4B—C5B—C6B—C7B178.9 (4)
C2A—C1A—C6A—C5A0.7 (6)C2B—C1B—C6B—C5B1.5 (6)
N2A—C1A—C6A—C5A177.4 (4)N2B—C1B—C6B—C5B176.8 (4)
C2A—C1A—C6A—C7A177.7 (4)C2B—C1B—C6B—C7B177.9 (4)
N2A—C1A—C6A—C7A4.2 (5)N2B—C1B—C6B—C7B3.8 (5)
C9A—O6A—C7A—C6A113.2 (4)C9B—O6B—C7B—C6B112.5 (4)
C9A—O6A—C7A—C8A127.9 (4)C9B—O6B—C7B—C8B127.1 (4)
C9A—O6A—C7A—C16A10.1 (3)C9B—O6B—C7B—C16B9.5 (3)
C5A—C6A—C7A—O6A47.3 (6)C5B—C6B—C7B—O6B45.6 (6)
C1A—C6A—C7A—O6A134.4 (4)C1B—C6B—C7B—O6B135.1 (4)
C5A—C6A—C7A—C8A171.0 (4)C5B—C6B—C7B—C8B170.6 (4)
C1A—C6A—C7A—C8A10.7 (4)C1B—C6B—C7B—C8B10.1 (4)
C5A—C6A—C7A—C16A59.3 (6)C5B—C6B—C7B—C16B59.2 (6)
C1A—C6A—C7A—C16A119.0 (4)C1B—C6B—C7B—C16B120.2 (4)
C1A—N2A—C8A—O5A167.1 (5)C21B—N2B—C8B—O5B12.4 (7)
C21A—N2A—C8A—O5A13.0 (7)C1B—N2B—C8B—O5B166.4 (4)
C1A—N2A—C8A—C7A11.6 (4)C21B—N2B—C8B—C7B170.1 (4)
C21A—N2A—C8A—C7A168.3 (4)C1B—N2B—C8B—C7B11.1 (4)
O6A—C7A—C8A—O5A38.0 (6)O6B—C7B—C8B—O5B36.7 (6)
C6A—C7A—C8A—O5A165.4 (5)C6B—C7B—C8B—O5B164.6 (4)
C16A—C7A—C8A—O5A62.8 (6)C16B—C7B—C8B—O5B63.4 (6)
O6A—C7A—C8A—N2A140.7 (3)O6B—C7B—C8B—N2B140.8 (3)
C6A—C7A—C8A—N2A13.4 (4)C6B—C7B—C8B—N2B12.9 (4)
C16A—C7A—C8A—N2A118.5 (4)C16B—C7B—C8B—N2B119.1 (4)
C17A—N1A—C9A—O6A89.1 (5)C7B—O6B—C9B—N1B119.3 (4)
C10A—N1A—C9A—O6A89.9 (4)C7B—O6B—C9B—C16B10.0 (3)
C17A—N1A—C9A—C16A172.3 (4)C17B—N1B—C9B—O6B86.6 (5)
C10A—N1A—C9A—C16A8.7 (5)C10B—N1B—C9B—O6B90.4 (4)
C7A—O6A—C9A—N1A119.9 (4)C17B—N1B—C9B—C16B174.1 (4)
C7A—O6A—C9A—C16A10.4 (3)C10B—N1B—C9B—C16B8.9 (5)
C17A—N1A—C10A—C11A5.3 (8)C17B—N1B—C10B—C15B176.6 (4)
C9A—N1A—C10A—C11A173.7 (5)C9B—N1B—C10B—C15B6.5 (5)
C17A—N1A—C10A—C15A174.7 (4)C17B—N1B—C10B—C11B3.3 (8)
C9A—N1A—C10A—C15A6.4 (5)C9B—N1B—C10B—C11B173.6 (5)
C15A—C10A—C11A—C12A1.9 (7)C15B—C10B—C11B—C12B1.2 (7)
N1A—C10A—C11A—C12A178.1 (5)N1B—C10B—C11B—C12B178.9 (5)
C10A—C11A—C12A—C13A1.2 (8)C10B—C11B—C12B—C13B0.6 (9)
C11A—C12A—C13A—C14A0.1 (9)C11B—C12B—C13B—C14B0.1 (9)
C12A—C13A—C14A—C15A0.2 (8)C12B—C13B—C14B—C15B0.3 (8)
C13A—C14A—C15A—C10A0.5 (7)C13B—C14B—C15B—C10B0.3 (7)
C13A—C14A—C15A—C16A177.0 (5)C13B—C14B—C15B—C16B177.3 (5)
C11A—C10A—C15A—C14A1.6 (7)C11B—C10B—C15B—C14B1.1 (7)
N1A—C10A—C15A—C14A178.4 (4)N1B—C10B—C15B—C14B179.0 (4)
C11A—C10A—C15A—C16A178.8 (4)C11B—C10B—C15B—C16B178.7 (4)
N1A—C10A—C15A—C16A1.2 (5)N1B—C10B—C15B—C16B1.4 (5)
C19A—O3A—C16A—C15A77.4 (5)C19B—O3B—C16B—C15B76.1 (5)
C19A—O3A—C16A—C9A164.6 (4)C19B—O3B—C16B—C9B164.8 (4)
C19A—O3A—C16A—C7A68.6 (5)C19B—O3B—C16B—C7B68.3 (5)
C14A—C15A—C16A—O3A64.8 (6)C14B—C15B—C16B—O3B63.5 (6)
C10A—C15A—C16A—O3A118.4 (4)C10B—C15B—C16B—O3B119.2 (4)
C14A—C15A—C16A—C9A172.9 (4)C14B—C15B—C16B—C9B173.3 (4)
C10A—C15A—C16A—C9A3.9 (4)C10B—C15B—C16B—C9B4.0 (5)
C14A—C15A—C16A—C7A81.4 (6)C14B—C15B—C16B—C7B81.2 (6)
C10A—C15A—C16A—C7A95.4 (4)C10B—C15B—C16B—C7B96.1 (4)
N1A—C9A—C16A—O3A117.8 (4)O6B—C9B—C16B—O3B126.9 (3)
O6A—C9A—C16A—O3A127.3 (3)N1B—C9B—C16B—O3B118.2 (4)
N1A—C9A—C16A—C15A7.6 (4)O6B—C9B—C16B—C15B107.1 (3)
O6A—C9A—C16A—C15A107.3 (3)N1B—C9B—C16B—C15B7.8 (4)
N1A—C9A—C16A—C7A124.4 (4)O6B—C9B—C16B—C7B9.2 (3)
O6A—C9A—C16A—C7A9.5 (3)N1B—C9B—C16B—C7B124.1 (4)
O6A—C7A—C16A—O3A121.3 (4)O6B—C7B—C16B—O3B121.5 (4)
C6A—C7A—C16A—O3A0.6 (6)C6B—C7B—C16B—O3B0.8 (5)
C8A—C7A—C16A—O3A124.2 (4)C8B—C7B—C16B—O3B123.8 (4)
O6A—C7A—C16A—C15A93.0 (4)O6B—C7B—C16B—C15B94.3 (4)
C6A—C7A—C16A—C15A145.0 (4)C6B—C7B—C16B—C15B145.0 (4)
C8A—C7A—C16A—C15A21.5 (5)C8B—C7B—C16B—C15B20.5 (5)
O6A—C7A—C16A—C9A9.6 (3)O6B—C7B—C16B—C9B9.2 (3)
C6A—C7A—C16A—C9A112.4 (4)C6B—C7B—C16B—C9B111.5 (4)
C8A—C7A—C16A—C9A124.1 (4)C8B—C7B—C16B—C9B123.9 (4)
C9A—N1A—C17A—O2A175.2 (4)C10B—N1B—C17B—O2B2.4 (7)
C10A—N1A—C17A—O2A3.6 (7)C9B—N1B—C17B—O2B174.1 (4)
C9A—N1A—C17A—C18A4.7 (6)C10B—N1B—C17B—C18B177.7 (4)
C10A—N1A—C17A—C18A176.4 (4)C9B—N1B—C17B—C18B5.9 (6)
C16A—O3A—C19A—O4A1.4 (7)C16B—O3B—C19B—O4B2.5 (7)
C16A—O3A—C19A—C20A177.9 (4)C16B—O3B—C19B—C20B177.8 (4)
C8A—N2A—C21A—O1A179.2 (4)C8B—N2B—C21B—O1B178.9 (4)
C1A—N2A—C21A—O1A0.8 (7)C1B—N2B—C21B—O1B0.3 (7)
C8A—N2A—C21A—C22A1.4 (7)C8B—N2B—C21B—C22B3.2 (7)
C1A—N2A—C21A—C22A178.6 (5)C1B—N2B—C21B—C22B178.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2B—H2B···O4Ai0.932.433.232 (6)144
C5A—H5A···O2Bii0.932.443.308 (7)156
C5B—H5B···O2A0.932.443.311 (6)155
C9A—H9A···O2Bii0.982.503.287 (6)138
C9B—H9B···O2A0.982.523.296 (5)136
C13A—H13A···O6Aiii0.932.593.360 (6)141
C14A—H14A···O4A0.932.413.046 (6)125
C14B—H14B···O4B0.932.423.062 (6)126
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x, y1, z; (iii) x+1/2, y+3/2, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC22H18N2O6C22H18N2O6
Mr406.38406.38
Crystal system, space groupTriclinic, P1Orthorhombic, Pna21
Temperature (K)183183
a, b, c (Å)8.9350 (4), 9.1189 (3), 13.4690 (6)14.5310 (2), 8.7676 (1), 30.0679 (1)
α, β, γ (°)75.897 (1), 89.831 (1), 62.201 (1)90, 90, 90
V3)933.64 (7)3830.71 (7)
Z28
Radiation typeMo KαMo Kα
µ (mm1)0.110.10
Crystal size (mm)0.38 × 0.32 × 0.200.50 × 0.30 × 0.22
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Siemens SMART CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.961, 0.9790.950, 0.978
No. of measured, independent and
observed [I > 2σ(I)] reflections
4475, 3160, 2252 17100, 3370, 2679
Rint0.0780.095
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.194, 0.95 0.048, 0.115, 0.99
No. of reflections31603370
No. of parameters275547
No. of restraints01
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.56, 0.520.35, 0.36

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected bond lengths (Å) for (I) top
O6—C91.454 (3)C7—C161.571 (4)
O6—C71.459 (3)C9—C161.531 (4)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O40.932.533.155 (4)125
C18—H18B···O4i0.962.543.271 (6)133
C20—H20B···O1ii0.962.593.323 (4)133
Symmetry codes: (i) x+1, y, z; (ii) x, y+2, z+2.
Selected bond lengths (Å) for (II) top
O6A—C7A1.442 (5)O6B—C9B1.452 (5)
O6A—C9A1.453 (5)O6B—C7B1.455 (5)
C7A—C16A1.567 (6)C7B—C16B1.581 (6)
C9A—C16A1.531 (6)C9B—C16B1.515 (6)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C2B—H2B···O4Ai0.932.433.232 (6)144
C5A—H5A···O2Bii0.932.443.308 (7)156
C5B—H5B···O2A0.932.443.311 (6)155
C9A—H9A···O2Bii0.982.503.287 (6)138
C9B—H9B···O2A0.982.523.296 (5)136
C13A—H13A···O6Aiii0.932.593.360 (6)141
C14A—H14A···O4A0.932.413.046 (6)125
C14B—H14B···O4B0.932.423.062 (6)126
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x, y1, z; (iii) x+1/2, y+3/2, z.
 

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