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The title compound, C15H19NO5, crystallizes in the monoclinic space group P21/c with four mol­ecules in the asymmetric unit, which differ from each other in the orientation of their methoxy groups. Of the three methoxy groups in each molecule, one lies close to the plane of the mol­ecule and the other two have an out-of-plane conformation where they point in opposite directions. In the crystal structure, four different types of π-stacks are observed and the mol­ecules pack in two different types of stacking sheets, with alternating mol­ecules A and B in one ribbon and alternating mol­ecules C and D in the other. The supramolecular structure is supported by C—H...O and π–π inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105035158/av1262sup1.cif
Contains datablocks III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105035158/av1262IIIsup2.hkl
Contains datablock III

CCDC reference: 294335

Comment top

The structure determination of the title compound, (III), was undertaken as part of our investigations of the crystal packing and hydrogen-bonding network of substituted indole derivatives. Previous synthetic work in our laboratory has reported the formation of benzocarbazoloquinone from compound (I) by alkali followed by polyphosphoric acid treatment in air (Rajeswaran & Srinivasan, 1994) (see scheme). Crystal structure analysis of this product indicated that it is not compound (II) but is the isomeric ketolactam, (III), which arises by the air-oxidation of the indole 3-carbon as well as of the indole 2-carbon and the side-chain methylene unit. The title compound is useful as a key precursor for the synthesis of analogues of the kinamycin group of antibiotics (Sullivan et al., 1992; Sato et al., 1985; Sato & Gould, 1985). Pyrroloisoquinoline exhibits pharmaceutical activities, such as antileukemic (Anderson et al., 1998), muscarinic agonistic (Loesel et al., 1998) and antidepressant (Elwan et al., 1996).

The title compound contains four molecules in the asymmetric unit, designated A, B, C and D. Fig. 1 shows a displacement ellipsoid plot of two symmetry-independent molecules (A and C) of the asymmetric unit. The four rings of the molecule lie in a plane and the dihedral angles between the isoquinoline and indole moieties are 4.9 (1), 1.6 (1), 3.2 (1) and 4.4 (1)° for molecules A, B, C and D, respectively. The corresponding bond lengths and angles in all four molecules show that there are no significant differences, except those at the methoxy groups. The methyl group bonded to atom O4A is disordered over two positions, with an occupancy ratio of 0.59 (4):0.41 (4). The orientations of the three methoxy groups on the phenyl ring are consistent with minimum steric interactions. Of the three methoxy groups, one group at C4 lies close to the plane of the molecule [C17—O3—C4—C3 torsion angles are −4.5 (4), −2.5 (4), 2.9 (4) and 11.0 (4)° for molecules A, B, C and D, respectively], while other two at C5 and C6 have an out-of-plane conformation where they point in opposite directions. Furthermore, the methoxy groups at C5 in molecules A and B point in the same direction, but this is opposite to what is observed in molecules C and D [C18—O4—C5—C6 torsion angles are −70.4 (10), −105 (2), −69.3 (3), 88.5 (4) and 86.3 (3)° for molecules A (major and minor component), B, C and D, respectively]. At C6 in molecules A and B, the methoxy group points in the same direction, but it points in the opposite direction in molecules C and D [C19—O5—C6—C5 torsion angles are −73.6 (3), −64.1 (3), 55.0 (4) and 62.0 (3)°, for molecules A, B, C and D, respectively].

The centroids of the four rings of the molecules are Cg1 (N1/C9–C11/C16), Cg2 (N1/C1/C2/C7–C9), Cg3 (C2–C7) and Cg4 (C11–C16). In the crystal structure, molecules A and Bviii, B and Aix, C and Dii, and D and Cx are linked by C—H···O hydrogen bonds to form dimeric pairs (see Table 2 for symmetry codes). These pairs are further reinforced by stacking interactions. Adjacent pairs, translated along the b direction, are linked by C—H···O and stacking interactions. Thus, these molecules pack in two types of stacking ribbons involving four different types of π-stacks, with molecules A and B alternating in one ribbon (stack AB) [(a) ABviii and the equivalent BAix; (b) ABvi and the equivalent BAvii], and molecules C and D alternating in the other ribbon (stack CD) [(c) CD; (d) CDii and the equivalent DCx]. In stack AB, the centroids Cg1 A and Cg1Bviii and Cg2 A and Cg2Bviii, and the equivalent pairs Cg1B and Cg1 Aix and Cg2B and Cg2 Aix, are separated by 3.574 (2) and 3.621 (1) Å, respectively. The centroids Cg2 A and Cg2Bvi and the equivalent pair Cg2B and Cg2 Avii are separated by 3.723 (1) Å. In stack CD, the centroids Cg2 C and Cg2D are separated by 3.599 (1) Å. Centroids Cg2 C and Cg2Dii and the equivalent pair Cg2D and Cg2Cx are separated by 3.715 (1) Å. The ribbons propagate along the b direction and adjacent ribbons are interlinked by C—H···O interactions, resulting in a molecular sheet (Fig. 2). Thus, the supramolecular structure is supported by C—H···O and ππ interactions (Table 2). Fig. 3 shows the molecular packing along the b axis.

Experimental top

2-Methyl-3-phenylthioindole was converted into the title compound, (III), via an oxidative cyclization by air during the application of polyphosphoric acid. [Please give grief details of quantities used] This work unambiguously supports the isomeric structure (III) (see scheme), instead of structure (II) as proposed in the original work (Rajeswaran & Srinivasan, 1994).

Refinement top

H atoms were fixed geometrically and treated as riding on their parent C atoms, with aromatic C—H = 0.93 Å and methyl C—H = 0.96 Å, and with Uiso(H) = 1.2Ueq(C), or 1.5Ueq(Cmethyl). [Please check added text] The methyl group bonded at O4A was disordered and the occupancy factors of the two positions were refined, with their sum constrained to unity [C18A = 0.59 (4) and C18E = 0.41 (4)].

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The asymmetric unit of (III), with the two crystallographically independent molecules, A and C, drawn with displacement ellipsoids at the 35% probability level. The minor disordered component of methyl (C18E) is also shown.
[Figure 2] Fig. 2. Part of the crystal structure of (III), showing the formation of ribbons running along the b direction. H atoms not involved in the interactions have been omitted for clarity. Symmetry-independent molecules AD are also marked.
[Figure 3] Fig. 3. The molecular packing of (III), viewed along the b axis.
1,2,3-Trimethoxy-5,11-dihydroindolo[1,2-b]isoquinoline-5,11-dione top
Crystal data top
C19H15NO5F(000) = 2816
Mr = 337.32Dx = 1.401 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 20.8934 (4) ÅCell parameters from 7530 reflections
b = 14.2400 (3) Åθ = 1.1–28.4°
c = 22.8886 (4) ŵ = 0.10 mm1
β = 110.014 (1)°T = 293 K
V = 6398.6 (2) Å3Slab, yellow
Z = 160.44 × 0.34 × 0.20 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
15541 independent reflections
Radiation source: fine-focus sealed tube7962 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 28.3°, θmin = 1.0°
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
h = 2724
Tmin = 0.739, Tmax = 0.980k = 1918
40492 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
15541 reflections(Δ/σ)max < 0.001
924 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C19H15NO5V = 6398.6 (2) Å3
Mr = 337.32Z = 16
Monoclinic, P21/cMo Kα radiation
a = 20.8934 (4) ŵ = 0.10 mm1
b = 14.2400 (3) ÅT = 293 K
c = 22.8886 (4) Å0.44 × 0.34 × 0.20 mm
β = 110.014 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
15541 independent reflections
Absorption correction: multi-scan
(SADABS; Siemens, 1996)
7962 reflections with I > 2σ(I)
Tmin = 0.739, Tmax = 0.980Rint = 0.048
40492 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0680 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 1.09Δρmax = 0.19 e Å3
15541 reflectionsΔρmin = 0.18 e Å3
924 parameters
Special details top

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*/UeqOcc. (<1)
O1A0.20487 (9)0.11398 (15)0.36912 (9)0.0745 (6)
O2A0.08839 (8)0.13022 (15)0.29829 (8)0.0703 (5)
O3A0.17597 (10)0.11527 (15)0.06190 (8)0.0766 (6)
O4A0.06484 (11)0.10323 (14)0.02963 (8)0.0766 (6)
O5A0.06517 (10)0.12089 (13)0.11984 (8)0.0687 (5)
N1A0.02670 (9)0.12392 (13)0.32419 (8)0.0465 (4)
C1A0.03875 (11)0.12796 (17)0.28176 (11)0.0494 (6)
C2A0.04291 (11)0.12628 (16)0.21608 (11)0.0473 (5)
C3A0.10757 (12)0.12461 (17)0.17094 (11)0.0543 (6)
H3A0.14590.12750.18270.065*
C4A0.11494 (13)0.11868 (18)0.10902 (11)0.0572 (6)
C5A0.05638 (14)0.11579 (18)0.09113 (12)0.0582 (6)
C6A0.00764 (13)0.11917 (17)0.13587 (12)0.0546 (6)
C7A0.01613 (12)0.12376 (16)0.19986 (11)0.0493 (6)
C8A0.08117 (12)0.12266 (17)0.24735 (11)0.0518 (6)
H8A0.12050.12230.23700.062*
C9A0.08563 (11)0.12210 (16)0.30760 (11)0.0470 (5)
C10A0.14522 (12)0.11751 (18)0.36534 (12)0.0534 (6)
C11A0.11662 (12)0.11534 (18)0.41585 (11)0.0534 (6)
C12A0.14827 (14)0.1077 (2)0.47989 (12)0.0643 (7)
H12A0.19550.10540.49760.077*
C13A0.10791 (15)0.1036 (2)0.51642 (13)0.0706 (8)
H13A0.12800.09810.55930.085*
C14A0.03808 (15)0.1077 (2)0.49003 (12)0.0674 (8)
H14A0.01200.10460.51580.081*
C15A0.00534 (13)0.11614 (19)0.42660 (12)0.0594 (7)
H15A0.04190.11960.40930.071*
C16A0.04595 (12)0.11925 (17)0.39016 (11)0.0492 (6)
C17A0.23582 (15)0.1111 (3)0.07846 (14)0.0858 (10)
H17A0.23400.05650.10350.129*
H17B0.27530.10770.04140.129*
H17C0.23850.16640.10160.129*
C18A0.0452 (12)0.1818 (8)0.0006 (7)0.083 (3)0.59 (4)
H18A0.06570.23820.00760.125*0.59 (4)
H18B0.06020.17090.04470.125*0.59 (4)
H18C0.00350.18830.01510.125*0.59 (4)
C18E0.084 (2)0.1783 (12)0.0112 (8)0.091 (6)0.41 (4)
H18D0.12490.20580.00900.137*0.41 (4)
H18E0.09170.15660.05280.137*0.41 (4)
H18F0.04820.22450.00020.137*0.41 (4)
C19A0.08242 (16)0.0339 (2)0.09762 (14)0.0839 (9)
H19A0.08230.01550.12610.126*
H19B0.12690.03880.09430.126*
H19C0.04960.02010.05750.126*
O1B0.10289 (11)0.87765 (15)0.46197 (9)0.0818 (6)
O2B0.08786 (9)0.86859 (15)0.20473 (9)0.0754 (6)
O3B0.16743 (9)0.87358 (15)0.08001 (9)0.0733 (5)
O4B0.22916 (9)0.88321 (14)0.16219 (9)0.0712 (5)
O5B0.15264 (9)0.87851 (13)0.29161 (9)0.0667 (5)
N1B0.09161 (10)0.87218 (14)0.30544 (9)0.0533 (5)
C1B0.05710 (13)0.87006 (18)0.24187 (12)0.0562 (6)
C2B0.01780 (12)0.87157 (16)0.22310 (11)0.0494 (6)
C3B0.05548 (13)0.87108 (17)0.16036 (12)0.0558 (6)
H3B0.03330.86880.13140.067*
C4B0.12549 (13)0.87399 (18)0.14023 (12)0.0570 (6)
C5B0.15952 (13)0.87747 (18)0.18426 (13)0.0566 (6)
C6B0.12193 (13)0.87831 (17)0.24705 (12)0.0548 (6)
C7B0.05012 (12)0.87470 (16)0.26822 (11)0.0499 (6)
C8B0.00961 (13)0.87542 (17)0.33256 (12)0.0549 (6)
H8B0.03040.87660.36260.066*
C9B0.05833 (13)0.87446 (17)0.34972 (11)0.0541 (6)
C10B0.11230 (14)0.87639 (19)0.41221 (13)0.0632 (7)
C11B0.17712 (14)0.8763 (2)0.40030 (13)0.0660 (7)
C12B0.24382 (16)0.8790 (2)0.44110 (15)0.0854 (9)
H12B0.25310.88270.48380.103*
C13B0.29571 (16)0.8760 (3)0.41734 (17)0.0902 (10)
H13B0.34070.87700.44400.108*
C14B0.28128 (15)0.8716 (2)0.35387 (17)0.0825 (9)
H14B0.31730.86910.33870.099*
C15B0.21531 (14)0.8707 (2)0.31189 (15)0.0699 (8)
H15B0.20650.86900.26920.084*
C16B0.16297 (13)0.87248 (18)0.33625 (13)0.0590 (6)
C17B0.13667 (15)0.8737 (2)0.03331 (13)0.0757 (8)
H17D0.11060.93010.03650.113*
H17E0.17150.87080.00700.113*
H17F0.10720.82020.03890.113*
C18B0.26519 (15)0.8038 (2)0.17292 (16)0.0839 (9)
H18G0.26010.75210.14790.126*
H18H0.31260.81920.16200.126*
H18I0.24710.78670.21610.126*
C19B0.19288 (16)0.9596 (2)0.29289 (15)0.0818 (9)
H19D0.16381.01360.30480.123*
H19E0.21560.94980.32240.123*
H19F0.22610.96950.25240.123*
O1C0.29171 (9)0.42247 (16)0.10131 (10)0.0830 (6)
O2C0.58567 (8)0.40921 (15)0.18602 (8)0.0714 (5)
O3C0.65988 (10)0.41833 (15)0.42171 (9)0.0787 (6)
O4C0.54598 (12)0.42306 (15)0.44843 (9)0.0851 (6)
O5C0.41769 (11)0.41359 (16)0.35125 (10)0.0865 (7)
N1C0.46995 (9)0.40700 (14)0.15461 (9)0.0503 (5)
C1C0.53378 (12)0.40949 (17)0.19955 (11)0.0508 (6)
C2C0.53425 (12)0.41257 (16)0.26403 (11)0.0492 (6)
C3C0.59712 (13)0.41341 (17)0.31123 (12)0.0558 (6)
H3C0.63680.41170.30150.067*
C4C0.60097 (14)0.41678 (18)0.37232 (12)0.0622 (7)
C5C0.54062 (15)0.41797 (19)0.38715 (12)0.0642 (7)
C6C0.47758 (14)0.41768 (19)0.34011 (13)0.0618 (7)
C7C0.47325 (12)0.41548 (17)0.27708 (12)0.0533 (6)
C8C0.40989 (12)0.41716 (17)0.22630 (12)0.0565 (6)
H8C0.36910.42100.23410.068*
C9C0.40914 (12)0.41328 (17)0.16793 (12)0.0536 (6)
C10C0.35164 (13)0.41473 (19)0.10763 (13)0.0604 (7)
C11C0.38416 (13)0.40563 (18)0.06013 (12)0.0594 (7)
C12C0.35566 (15)0.4010 (2)0.00439 (13)0.0724 (8)
H12C0.30870.40400.02420.087*
C13C0.39882 (16)0.3919 (2)0.03824 (14)0.0770 (8)
H13C0.38090.38930.08140.092*
C14C0.46828 (16)0.3865 (2)0.00830 (14)0.0733 (8)
H14C0.49630.38000.03200.088*
C15C0.49780 (14)0.39063 (19)0.05578 (13)0.0636 (7)
H15C0.54470.38690.07540.076*
C16C0.45442 (12)0.40052 (17)0.08920 (11)0.0520 (6)
C17C0.72249 (15)0.4208 (2)0.40914 (14)0.0817 (9)
H17G0.72650.36490.38720.122*
H17H0.76010.42440.44760.122*
H17I0.72290.47490.38420.122*
C18C0.5450 (3)0.3354 (3)0.47756 (17)0.1292 (16)
H18J0.50440.30170.45450.194*
H18K0.54570.34580.51920.194*
H18L0.58430.29940.47870.194*
C19C0.40427 (19)0.4814 (3)0.39083 (18)0.1070 (12)
H19G0.42460.46170.43330.160*
H19H0.35590.48760.38080.160*
H19I0.42320.54070.38520.160*
O1D0.60310 (11)0.14356 (17)0.41800 (9)0.0883 (7)
O2D0.56043 (9)0.18428 (15)0.15597 (9)0.0732 (5)
O3D0.30426 (9)0.15391 (14)0.04904 (8)0.0712 (5)
O4D0.25203 (8)0.14831 (13)0.13927 (9)0.0668 (5)
O5D0.33783 (9)0.15645 (13)0.26516 (8)0.0674 (5)
N1D0.57485 (10)0.17260 (14)0.25914 (9)0.0526 (5)
C1D0.53493 (12)0.17572 (17)0.19630 (12)0.0539 (6)
C2D0.46117 (12)0.16808 (16)0.18417 (11)0.0487 (6)
C3D0.41901 (13)0.16586 (17)0.12226 (12)0.0546 (6)
H3D0.43770.16910.09080.066*
C4D0.34987 (13)0.15894 (18)0.10758 (12)0.0554 (6)
C5D0.32138 (11)0.15636 (17)0.15554 (12)0.0513 (6)
C6D0.36320 (12)0.15664 (17)0.21712 (12)0.0539 (6)
C7D0.43477 (12)0.16160 (16)0.23294 (11)0.0501 (6)
C8D0.48068 (13)0.15793 (18)0.29582 (11)0.0556 (6)
H8D0.46410.15280.32850.067*
C9D0.54765 (13)0.16197 (17)0.30695 (11)0.0539 (6)
C10D0.60635 (14)0.1561 (2)0.36631 (14)0.0670 (7)
C11D0.66810 (13)0.16628 (19)0.34881 (13)0.0634 (7)
C12D0.73669 (15)0.1669 (2)0.38394 (15)0.0830 (9)
H12D0.75120.15830.42680.100*
C13D0.78318 (15)0.1807 (2)0.35407 (18)0.0863 (10)
H13D0.82950.18200.37710.104*
C14D0.76187 (14)0.1924 (2)0.29116 (17)0.0798 (9)
H14D0.79420.20180.27220.096*
C15D0.69338 (13)0.1907 (2)0.25453 (14)0.0699 (8)
H15D0.67930.19840.21160.084*
C16D0.64714 (12)0.17689 (18)0.28471 (13)0.0574 (6)
C17D0.33166 (15)0.1389 (2)0.00053 (13)0.0811 (9)
H17J0.35790.19270.00270.122*
H17K0.29510.12970.03810.122*
H17L0.36040.08440.00990.122*
C18D0.21675 (14)0.2319 (2)0.13715 (17)0.0917 (10)
H18M0.23380.26240.17690.138*
H18N0.16910.21870.12710.138*
H18O0.22300.27230.10600.138*
C19D0.29749 (15)0.0765 (2)0.26941 (14)0.0741 (8)
H19J0.25950.07020.23140.111*
H19K0.28110.08510.30340.111*
H19L0.32500.02080.27620.111*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1A0.0409 (10)0.1109 (16)0.0744 (13)0.0007 (10)0.0229 (9)0.0031 (11)
O2A0.0413 (10)0.1151 (16)0.0593 (11)0.0013 (9)0.0236 (8)0.0093 (10)
O3A0.0671 (13)0.0994 (15)0.0537 (11)0.0070 (11)0.0082 (10)0.0070 (10)
O4A0.1062 (16)0.0762 (14)0.0495 (11)0.0106 (11)0.0294 (11)0.0074 (9)
O5A0.0755 (13)0.0771 (13)0.0690 (12)0.0138 (10)0.0449 (10)0.0113 (9)
N1A0.0412 (11)0.0561 (12)0.0467 (11)0.0039 (9)0.0209 (9)0.0045 (9)
C1A0.0409 (13)0.0583 (15)0.0517 (14)0.0003 (11)0.0194 (11)0.0032 (11)
C2A0.0482 (14)0.0458 (13)0.0494 (13)0.0029 (10)0.0186 (11)0.0048 (10)
C3A0.0502 (14)0.0595 (15)0.0534 (15)0.0029 (11)0.0182 (12)0.0061 (11)
C4A0.0618 (16)0.0545 (15)0.0491 (15)0.0037 (12)0.0107 (13)0.0029 (11)
C5A0.0764 (18)0.0524 (15)0.0502 (15)0.0107 (13)0.0275 (14)0.0079 (11)
C6A0.0621 (16)0.0537 (15)0.0546 (15)0.0135 (12)0.0283 (13)0.0088 (11)
C7A0.0547 (14)0.0452 (13)0.0544 (14)0.0066 (11)0.0269 (12)0.0077 (10)
C8A0.0444 (13)0.0586 (15)0.0598 (15)0.0054 (11)0.0274 (12)0.0036 (12)
C9A0.0398 (12)0.0522 (13)0.0531 (14)0.0059 (10)0.0212 (11)0.0033 (11)
C10A0.0419 (14)0.0632 (16)0.0576 (15)0.0031 (11)0.0204 (11)0.0006 (12)
C11A0.0488 (14)0.0591 (15)0.0537 (15)0.0030 (11)0.0193 (12)0.0030 (11)
C12A0.0511 (15)0.083 (2)0.0578 (16)0.0043 (13)0.0173 (13)0.0037 (13)
C13A0.074 (2)0.090 (2)0.0458 (15)0.0061 (16)0.0176 (14)0.0015 (13)
C14A0.0723 (19)0.086 (2)0.0518 (16)0.0066 (15)0.0318 (14)0.0053 (13)
C15A0.0517 (15)0.0775 (18)0.0565 (16)0.0044 (13)0.0281 (12)0.0066 (13)
C16A0.0507 (14)0.0524 (14)0.0460 (13)0.0055 (11)0.0185 (11)0.0043 (10)
C17A0.0586 (18)0.118 (3)0.0660 (19)0.0049 (18)0.0025 (15)0.0060 (18)
C18A0.117 (8)0.072 (4)0.069 (6)0.005 (6)0.044 (7)0.014 (4)
C18E0.130 (16)0.075 (6)0.065 (6)0.001 (10)0.028 (10)0.001 (5)
C19A0.102 (2)0.084 (2)0.085 (2)0.0076 (18)0.0570 (19)0.0041 (17)
O1B0.0890 (15)0.1031 (16)0.0609 (12)0.0154 (12)0.0355 (11)0.0014 (11)
O2B0.0643 (12)0.1102 (16)0.0660 (12)0.0014 (11)0.0407 (10)0.0012 (11)
O3B0.0627 (12)0.0985 (15)0.0629 (12)0.0014 (10)0.0270 (10)0.0100 (10)
O4B0.0523 (11)0.0805 (13)0.0877 (14)0.0110 (9)0.0328 (10)0.0263 (10)
O5B0.0667 (11)0.0744 (12)0.0779 (12)0.0120 (9)0.0490 (10)0.0161 (9)
N1B0.0544 (13)0.0568 (12)0.0577 (13)0.0036 (10)0.0308 (10)0.0009 (10)
C1B0.0621 (16)0.0545 (15)0.0638 (17)0.0003 (12)0.0368 (14)0.0057 (12)
C2B0.0554 (14)0.0457 (13)0.0554 (15)0.0019 (11)0.0295 (12)0.0048 (11)
C3B0.0622 (16)0.0554 (15)0.0602 (16)0.0023 (12)0.0346 (13)0.0035 (12)
C4B0.0574 (16)0.0576 (15)0.0602 (16)0.0026 (12)0.0253 (13)0.0107 (12)
C5B0.0528 (15)0.0545 (15)0.0702 (18)0.0072 (12)0.0309 (13)0.0138 (12)
C6B0.0600 (16)0.0516 (14)0.0661 (17)0.0063 (12)0.0387 (14)0.0133 (12)
C7B0.0580 (15)0.0445 (13)0.0576 (15)0.0041 (11)0.0331 (12)0.0084 (11)
C8B0.0614 (16)0.0549 (15)0.0609 (16)0.0013 (12)0.0369 (13)0.0042 (12)
C9B0.0646 (17)0.0515 (14)0.0574 (15)0.0048 (12)0.0351 (13)0.0028 (11)
C10B0.0703 (18)0.0644 (17)0.0617 (17)0.0105 (14)0.0314 (14)0.0019 (13)
C11B0.0630 (18)0.0729 (18)0.0665 (18)0.0123 (14)0.0279 (15)0.0027 (14)
C12B0.078 (2)0.108 (3)0.070 (2)0.0219 (19)0.0253 (17)0.0040 (18)
C13B0.062 (2)0.114 (3)0.092 (3)0.0161 (18)0.0235 (18)0.006 (2)
C14B0.0545 (18)0.096 (2)0.105 (3)0.0139 (16)0.0371 (18)0.0043 (19)
C15B0.0636 (18)0.0758 (19)0.081 (2)0.0097 (14)0.0386 (16)0.0023 (15)
C16B0.0575 (16)0.0558 (16)0.0699 (17)0.0109 (12)0.0299 (13)0.0003 (12)
C17B0.078 (2)0.092 (2)0.0623 (18)0.0070 (16)0.0312 (16)0.0005 (15)
C18B0.0655 (18)0.081 (2)0.109 (3)0.0061 (16)0.0351 (17)0.0137 (18)
C19B0.090 (2)0.073 (2)0.104 (2)0.0093 (17)0.0621 (19)0.0004 (17)
O1C0.0392 (11)0.1174 (18)0.0901 (15)0.0032 (10)0.0190 (10)0.0084 (12)
O2C0.0441 (10)0.1130 (16)0.0624 (11)0.0047 (10)0.0248 (9)0.0123 (10)
O3C0.0773 (14)0.0968 (15)0.0523 (11)0.0160 (11)0.0096 (10)0.0012 (10)
O4C0.1165 (17)0.0902 (15)0.0555 (12)0.0279 (13)0.0384 (11)0.0158 (10)
O5C0.0845 (14)0.1079 (17)0.0885 (15)0.0326 (12)0.0570 (12)0.0337 (12)
N1C0.0424 (11)0.0579 (12)0.0527 (12)0.0040 (9)0.0190 (9)0.0048 (9)
C1C0.0408 (13)0.0585 (15)0.0553 (15)0.0047 (11)0.0192 (12)0.0062 (11)
C2C0.0480 (14)0.0481 (14)0.0523 (14)0.0062 (10)0.0181 (11)0.0055 (10)
C3C0.0568 (15)0.0548 (15)0.0570 (15)0.0086 (12)0.0209 (13)0.0045 (11)
C4C0.0671 (17)0.0604 (16)0.0546 (16)0.0155 (13)0.0149 (14)0.0046 (12)
C5C0.083 (2)0.0590 (16)0.0575 (17)0.0208 (14)0.0332 (15)0.0140 (12)
C6C0.0665 (18)0.0645 (17)0.0645 (17)0.0176 (13)0.0353 (15)0.0139 (13)
C7C0.0551 (15)0.0508 (14)0.0613 (16)0.0124 (11)0.0291 (13)0.0118 (11)
C8C0.0440 (14)0.0633 (16)0.0689 (17)0.0095 (11)0.0279 (13)0.0124 (13)
C9C0.0411 (13)0.0574 (15)0.0662 (17)0.0047 (11)0.0236 (12)0.0049 (12)
C10C0.0454 (15)0.0642 (17)0.0684 (17)0.0057 (12)0.0153 (13)0.0050 (13)
C11C0.0519 (16)0.0618 (17)0.0632 (17)0.0010 (12)0.0183 (13)0.0003 (12)
C12C0.0626 (18)0.084 (2)0.0625 (18)0.0021 (15)0.0103 (15)0.0043 (15)
C13C0.081 (2)0.088 (2)0.0540 (17)0.0039 (17)0.0135 (16)0.0063 (15)
C14C0.080 (2)0.083 (2)0.0622 (18)0.0008 (16)0.0307 (16)0.0002 (14)
C15C0.0574 (16)0.0763 (19)0.0607 (17)0.0014 (13)0.0251 (13)0.0006 (13)
C16C0.0507 (15)0.0537 (15)0.0501 (14)0.0017 (11)0.0152 (11)0.0000 (11)
C17C0.0646 (19)0.095 (2)0.0689 (19)0.0036 (17)0.0013 (15)0.0080 (16)
C18C0.219 (5)0.104 (3)0.077 (2)0.013 (3)0.066 (3)0.011 (2)
C19C0.128 (3)0.100 (3)0.129 (3)0.018 (2)0.090 (3)0.028 (2)
O1D0.0825 (15)0.1246 (19)0.0555 (12)0.0006 (13)0.0207 (11)0.0068 (12)
O2D0.0591 (11)0.1063 (16)0.0641 (12)0.0022 (10)0.0340 (10)0.0033 (10)
O3D0.0576 (11)0.0968 (15)0.0564 (12)0.0004 (10)0.0157 (9)0.0031 (10)
O4D0.0480 (10)0.0661 (12)0.0879 (14)0.0007 (9)0.0252 (9)0.0059 (10)
O5D0.0650 (11)0.0809 (13)0.0706 (12)0.0076 (10)0.0416 (10)0.0123 (9)
N1D0.0449 (11)0.0579 (13)0.0591 (13)0.0031 (9)0.0231 (10)0.0013 (9)
C1D0.0545 (15)0.0563 (15)0.0577 (16)0.0015 (11)0.0278 (13)0.0022 (11)
C2D0.0496 (14)0.0475 (14)0.0543 (14)0.0021 (10)0.0244 (12)0.0013 (10)
C3D0.0558 (15)0.0578 (15)0.0560 (15)0.0011 (12)0.0265 (13)0.0005 (11)
C4D0.0519 (15)0.0587 (16)0.0555 (15)0.0015 (12)0.0183 (12)0.0021 (11)
C5D0.0413 (14)0.0518 (14)0.0638 (16)0.0008 (10)0.0219 (12)0.0019 (11)
C6D0.0520 (15)0.0531 (15)0.0671 (17)0.0001 (11)0.0340 (13)0.0067 (12)
C7D0.0539 (15)0.0483 (14)0.0549 (15)0.0020 (11)0.0273 (12)0.0044 (11)
C8D0.0572 (16)0.0617 (16)0.0550 (15)0.0011 (12)0.0284 (13)0.0032 (12)
C9D0.0554 (15)0.0538 (15)0.0550 (15)0.0003 (12)0.0222 (12)0.0006 (11)
C10D0.0674 (18)0.0710 (18)0.0621 (18)0.0030 (14)0.0213 (15)0.0020 (14)
C11D0.0537 (16)0.0656 (17)0.0681 (18)0.0061 (13)0.0175 (13)0.0045 (13)
C12D0.065 (2)0.101 (2)0.072 (2)0.0062 (17)0.0091 (16)0.0021 (17)
C13D0.0500 (17)0.098 (3)0.104 (3)0.0098 (16)0.0170 (18)0.000 (2)
C14D0.0533 (18)0.085 (2)0.106 (3)0.0087 (15)0.0335 (17)0.0047 (18)
C15D0.0474 (16)0.086 (2)0.0811 (19)0.0068 (14)0.0276 (14)0.0044 (15)
C16D0.0461 (14)0.0552 (16)0.0700 (18)0.0044 (11)0.0189 (13)0.0018 (12)
C17D0.075 (2)0.115 (3)0.0528 (17)0.0090 (18)0.0215 (15)0.0039 (16)
C18D0.0558 (17)0.080 (2)0.135 (3)0.0128 (16)0.0277 (18)0.012 (2)
C19D0.0748 (19)0.077 (2)0.085 (2)0.0023 (15)0.0464 (16)0.0101 (16)
Geometric parameters (Å, º) top
O1A—C10A1.221 (3)C19B—H19E0.9600
O2A—C1A1.220 (3)C19B—H19F0.9600
O3A—C4A1.360 (3)O1C—C10C1.215 (3)
O3A—C17A1.427 (3)O2C—C1C1.225 (3)
O4A—C5A1.369 (3)O3C—C4C1.357 (3)
O4A—C18E1.386 (17)O3C—C17C1.433 (3)
O4A—C18A1.447 (12)O4C—C5C1.370 (3)
O5A—C6A1.372 (3)O4C—C18C1.419 (4)
O5A—C19A1.431 (3)O5C—C6C1.361 (3)
N1A—C1A1.381 (3)O5C—C19C1.416 (4)
N1A—C9A1.407 (3)N1C—C1C1.378 (3)
N1A—C16A1.425 (3)N1C—C9C1.407 (3)
C1A—C2A1.476 (3)N1C—C16C1.422 (3)
C2A—C3A1.392 (3)C1C—C2C1.473 (3)
C2A—C7A1.405 (3)C2C—C3C1.386 (3)
C3A—C4A1.375 (3)C2C—C7C1.406 (3)
C3A—H3A0.9300C3C—C4C1.374 (4)
C4A—C5A1.418 (4)C3C—H3C0.9300
C5A—C6A1.379 (4)C4C—C5C1.414 (4)
C6A—C7A1.415 (3)C5C—C6C1.387 (4)
C7A—C8A1.420 (3)C6C—C7C1.415 (3)
C8A—C9A1.350 (3)C7C—C8C1.432 (4)
C8A—H8A0.9300C8C—C9C1.332 (3)
C9A—C10A1.475 (3)C8C—H8C0.9300
C10A—C11A1.472 (3)C9C—C10C1.488 (4)
C11A—C12A1.391 (4)C10C—C11C1.472 (4)
C11A—C16A1.391 (3)C11C—C16C1.391 (3)
C12A—C13A1.377 (4)C11C—C12C1.392 (4)
C12A—H12A0.9300C12C—C13C1.381 (4)
C13A—C14A1.376 (4)C12C—H12C0.9300
C13A—H13A0.9300C13C—C14C1.379 (4)
C14A—C15A1.382 (4)C13C—H13C0.9300
C14A—H14A0.9300C14C—C15C1.384 (4)
C15A—C16A1.379 (3)C14C—H14C0.9300
C15A—H15A0.9300C15C—C16C1.379 (3)
C17A—H17A0.9600C15C—H15C0.9300
C17A—H17B0.9600C17C—H17G0.9600
C17A—H17C0.9600C17C—H17H0.9600
C18A—H18A0.9600C17C—H17I0.9600
C18A—H18B0.9600C18C—H18J0.9600
C18A—H18C0.9600C18C—H18K0.9600
C18E—H18D0.9600C18C—H18L0.9600
C18E—H18E0.9600C19C—H19G0.9600
C18E—H18F0.9600C19C—H19H0.9600
C19A—H19A0.9600C19C—H19I0.9600
C19A—H19B0.9600O1D—C10D1.221 (3)
C19A—H19C0.9600O2D—C1D1.220 (3)
O1B—C10B1.220 (3)O3D—C4D1.354 (3)
O2B—C1B1.229 (3)O3D—C17D1.429 (3)
O3B—C4B1.357 (3)O4D—C5D1.372 (3)
O3B—C17B1.423 (3)O4D—C18D1.392 (3)
O4B—C5B1.370 (3)O5D—C6D1.374 (3)
O4B—C18B1.425 (3)O5D—C19D1.440 (3)
O5B—C6B1.378 (3)N1D—C1D1.395 (3)
O5B—C19B1.434 (3)N1D—C9D1.403 (3)
N1B—C1B1.385 (3)N1D—C16D1.422 (3)
N1B—C9B1.412 (3)C1D—C2D1.473 (3)
N1B—C16B1.414 (3)C2D—C3D1.389 (3)
C1B—C2B1.475 (3)C2D—C7D1.407 (3)
C2B—C3B1.381 (3)C3D—C4D1.370 (3)
C2B—C7B1.415 (3)C3D—H3D0.9300
C3B—C4B1.376 (3)C4D—C5D1.417 (3)
C3B—H3B0.9300C5D—C6D1.381 (4)
C4B—C5B1.419 (3)C6D—C7D1.415 (3)
C5B—C6B1.382 (4)C7D—C8D1.432 (3)
C6B—C7B1.411 (3)C8D—C9D1.335 (3)
C7B—C8B1.425 (4)C8D—H8D0.9300
C8B—C9B1.337 (3)C9D—C10D1.489 (4)
C8B—H8B0.9300C10D—C11D1.483 (4)
C9B—C10B1.488 (4)C11D—C12D1.383 (4)
C10B—C11B1.470 (4)C11D—C16D1.388 (4)
C11B—C12B1.387 (4)C12D—C13D1.380 (4)
C11B—C16B1.394 (4)C12D—H12D0.9300
C12B—C13B1.370 (4)C13D—C14D1.364 (4)
C12B—H12B0.9300C13D—H13D0.9300
C13B—C14B1.380 (5)C14D—C15D1.389 (4)
C13B—H13B0.9300C14D—H14D0.9300
C14B—C15B1.384 (4)C15D—C16D1.381 (4)
C14B—H14B0.9300C15D—H15D0.9300
C15B—C16B1.387 (3)C17D—H17J0.9600
C15B—H15B0.9300C17D—H17K0.9600
C17B—H17D0.9600C17D—H17L0.9600
C17B—H17E0.9600C18D—H18M0.9600
C17B—H17F0.9600C18D—H18N0.9600
C18B—H18G0.9600C18D—H18O0.9600
C18B—H18H0.9600C19D—H19J0.9600
C18B—H18I0.9600C19D—H19K0.9600
C19B—H19D0.9600C19D—H19L0.9600
C4A—O3A—C17A117.4 (2)H19D—C19B—H19F109.5
C5A—O4A—C18E120.0 (8)H19E—C19B—H19F109.5
C5A—O4A—C18A115.7 (6)C4C—O3C—C17C117.6 (2)
C6A—O5A—C19A115.5 (2)C5C—O4C—C18C115.2 (2)
C1A—N1A—C9A123.9 (2)C6C—O5C—C19C119.1 (2)
C1A—N1A—C16A126.8 (2)C1C—N1C—C9C123.5 (2)
C9A—N1A—C16A109.2 (2)C1C—N1C—C16C127.0 (2)
O2A—C1A—N1A121.7 (2)C9C—N1C—C16C109.6 (2)
O2A—C1A—C2A123.8 (2)O2C—C1C—N1C121.7 (2)
N1A—C1A—C2A114.5 (2)O2C—C1C—C2C123.4 (2)
C3A—C2A—C7A121.3 (2)N1C—C1C—C2C114.9 (2)
C3A—C2A—C1A117.4 (2)C3C—C2C—C7C121.4 (2)
C7A—C2A—C1A121.2 (2)C3C—C2C—C1C117.4 (2)
C4A—C3A—C2A120.3 (2)C7C—C2C—C1C121.2 (2)
C4A—C3A—H3A119.9C4C—C3C—C2C120.2 (2)
C2A—C3A—H3A119.9C4C—C3C—H3C119.9
O3A—C4A—C3A124.3 (2)C2C—C3C—H3C119.9
O3A—C4A—C5A115.9 (2)O3C—C4C—C3C124.7 (3)
C3A—C4A—C5A119.8 (2)O3C—C4C—C5C115.4 (2)
O4A—C5A—C6A121.3 (2)C3C—C4C—C5C119.9 (2)
O4A—C5A—C4A118.7 (2)O4C—C5C—C6C121.2 (2)
C6A—C5A—C4A119.9 (2)O4C—C5C—C4C118.6 (3)
O5A—C6A—C5A121.2 (2)C6C—C5C—C4C120.1 (2)
O5A—C6A—C7A117.7 (2)O5C—C6C—C5C123.0 (2)
C5A—C6A—C7A121.1 (2)O5C—C6C—C7C116.6 (2)
C2A—C7A—C6A117.7 (2)C5C—C6C—C7C120.3 (2)
C2A—C7A—C8A119.6 (2)C2C—C7C—C6C118.1 (2)
C6A—C7A—C8A122.7 (2)C2C—C7C—C8C118.8 (2)
C9A—C8A—C7A119.7 (2)C6C—C7C—C8C123.1 (2)
C9A—C8A—H8A120.2C9C—C8C—C7C120.2 (2)
C7A—C8A—H8A120.2C9C—C8C—H8C119.9
C8A—C9A—N1A121.0 (2)C7C—C8C—H8C119.9
C8A—C9A—C10A131.1 (2)C8C—C9C—N1C121.2 (2)
N1A—C9A—C10A107.9 (2)C8C—C9C—C10C131.2 (2)
O1A—C10A—C11A128.5 (2)N1C—C9C—C10C107.6 (2)
O1A—C10A—C9A126.4 (2)O1C—C10C—C11C129.6 (3)
C11A—C10A—C9A105.0 (2)O1C—C10C—C9C125.7 (3)
C12A—C11A—C16A120.1 (2)C11C—C10C—C9C104.7 (2)
C12A—C11A—C10A130.9 (2)C16C—C11C—C12C120.2 (2)
C16A—C11A—C10A108.9 (2)C16C—C11C—C10C109.2 (2)
C13A—C12A—C11A118.3 (2)C12C—C11C—C10C130.5 (3)
C13A—C12A—H12A120.8C13C—C12C—C11C118.4 (3)
C11A—C12A—H12A120.8C13C—C12C—H12C120.8
C14A—C13A—C12A120.6 (3)C11C—C12C—H12C120.8
C14A—C13A—H13A119.7C14C—C13C—C12C120.3 (3)
C12A—C13A—H13A119.7C14C—C13C—H13C119.8
C13A—C14A—C15A122.3 (2)C12C—C13C—H13C119.8
C13A—C14A—H14A118.9C13C—C14C—C15C122.4 (3)
C15A—C14A—H14A118.9C13C—C14C—H14C118.8
C16A—C15A—C14A116.9 (2)C15C—C14C—H14C118.8
C16A—C15A—H15A121.6C16C—C15C—C14C116.9 (3)
C14A—C15A—H15A121.6C16C—C15C—H15C121.5
C15A—C16A—C11A121.8 (2)C14C—C15C—H15C121.5
C15A—C16A—N1A129.3 (2)C15C—C16C—C11C121.8 (2)
C11A—C16A—N1A108.9 (2)C15C—C16C—N1C129.4 (2)
O3A—C17A—H17A109.5C11C—C16C—N1C108.9 (2)
O3A—C17A—H17B109.5O3C—C17C—H17G109.5
H17A—C17A—H17B109.5O3C—C17C—H17H109.5
O3A—C17A—H17C109.5H17G—C17C—H17H109.5
H17A—C17A—H17C109.5O3C—C17C—H17I109.5
H17B—C17A—H17C109.5H17G—C17C—H17I109.5
O4A—C18A—H18A109.5H17H—C17C—H17I109.5
O4A—C18A—H18B109.5O4C—C18C—H18J109.5
O4A—C18A—H18C109.5O4C—C18C—H18K109.5
O4A—C18E—H18D109.5H18J—C18C—H18K109.5
O4A—C18E—H18E109.5O4C—C18C—H18L109.5
H18D—C18E—H18E109.5H18J—C18C—H18L109.5
O4A—C18E—H18F109.5H18K—C18C—H18L109.5
H18D—C18E—H18F109.5O5C—C19C—H19G109.5
H18E—C18E—H18F109.5O5C—C19C—H19H109.5
O5A—C19A—H19A109.5H19G—C19C—H19H109.5
O5A—C19A—H19B109.5O5C—C19C—H19I109.5
H19A—C19A—H19B109.5H19G—C19C—H19I109.5
O5A—C19A—H19C109.5H19H—C19C—H19I109.5
H19A—C19A—H19C109.5C4D—O3D—C17D116.3 (2)
H19B—C19A—H19C109.5C5D—O4D—C18D115.8 (2)
C4B—O3B—C17B117.5 (2)C6D—O5D—C19D116.8 (2)
C5B—O4B—C18B116.5 (2)C1D—N1D—C9D123.3 (2)
C6B—O5B—C19B116.2 (2)C1D—N1D—C16D126.8 (2)
C1B—N1B—C9B123.2 (2)C9D—N1D—C16D109.9 (2)
C1B—N1B—C16B127.2 (2)O2D—C1D—N1D121.5 (2)
C9B—N1B—C16B109.6 (2)O2D—C1D—C2D124.4 (2)
O2B—C1B—N1B121.3 (2)N1D—C1D—C2D114.2 (2)
O2B—C1B—C2B123.6 (2)C3D—C2D—C7D121.6 (2)
N1B—C1B—C2B115.1 (2)C3D—C2D—C1D116.8 (2)
C3B—C2B—C7B121.0 (2)C7D—C2D—C1D121.6 (2)
C3B—C2B—C1B118.2 (2)C4D—C3D—C2D119.9 (2)
C7B—C2B—C1B120.8 (2)C4D—C3D—H3D120.0
C4B—C3B—C2B120.7 (2)C2D—C3D—H3D120.0
C4B—C3B—H3B119.7O3D—C4D—C3D124.9 (2)
C2B—C3B—H3B119.7O3D—C4D—C5D115.2 (2)
O3B—C4B—C3B125.7 (2)C3D—C4D—C5D119.9 (2)
O3B—C4B—C5B114.5 (2)O4D—C5D—C6D121.2 (2)
C3B—C4B—C5B119.8 (2)O4D—C5D—C4D118.5 (2)
O4B—C5B—C6B122.5 (2)C6D—C5D—C4D120.3 (2)
O4B—C5B—C4B117.9 (2)O5D—C6D—C5D122.3 (2)
C6B—C5B—C4B119.6 (2)O5D—C6D—C7D117.3 (2)
O5B—C6B—C5B121.8 (2)C5D—C6D—C7D120.4 (2)
O5B—C6B—C7B117.1 (2)C2D—C7D—C6D117.8 (2)
C5B—C6B—C7B121.1 (2)C2D—C7D—C8D119.4 (2)
C6B—C7B—C2B117.9 (2)C6D—C7D—C8D122.8 (2)
C6B—C7B—C8B122.7 (2)C9D—C8D—C7D119.2 (2)
C2B—C7B—C8B119.4 (2)C9D—C8D—H8D120.4
C9B—C8B—C7B119.9 (2)C7D—C8D—H8D120.4
C9B—C8B—H8B120.0C8D—C9D—N1D122.3 (2)
C7B—C8B—H8B120.0C8D—C9D—C10D130.8 (2)
C8B—C9B—N1B121.6 (2)N1D—C9D—C10D106.9 (2)
C8B—C9B—C10B131.4 (2)O1D—C10D—C11D128.2 (3)
N1B—C9B—C10B107.0 (2)O1D—C10D—C9D126.2 (3)
O1B—C10B—C11B128.7 (3)C11D—C10D—C9D105.6 (2)
O1B—C10B—C9B125.9 (2)C12D—C11D—C16D120.2 (3)
C11B—C10B—C9B105.4 (2)C12D—C11D—C10D131.9 (3)
C12B—C11B—C16B120.8 (3)C16D—C11D—C10D107.9 (2)
C12B—C11B—C10B130.7 (3)C13D—C12D—C11D118.6 (3)
C16B—C11B—C10B108.5 (2)C13D—C12D—H12D120.7
C13B—C12B—C11B118.7 (3)C11D—C12D—H12D120.7
C13B—C12B—H12B120.6C14D—C13D—C12D120.6 (3)
C11B—C12B—H12B120.6C14D—C13D—H13D119.7
C12B—C13B—C14B120.1 (3)C12D—C13D—H13D119.7
C12B—C13B—H13B119.9C13D—C14D—C15D122.1 (3)
C14B—C13B—H13B119.9C13D—C14D—H14D118.9
C13B—C14B—C15B122.5 (3)C15D—C14D—H14D118.9
C13B—C14B—H14B118.7C16D—C15D—C14D117.0 (3)
C15B—C14B—H14B118.7C16D—C15D—H15D121.5
C14B—C15B—C16B117.1 (3)C14D—C15D—H15D121.5
C14B—C15B—H15B121.5C15D—C16D—C11D121.5 (2)
C16B—C15B—H15B121.5C15D—C16D—N1D128.8 (2)
C15B—C16B—C11B120.7 (3)C11D—C16D—N1D109.7 (2)
C15B—C16B—N1B129.9 (3)O3D—C17D—H17J109.5
C11B—C16B—N1B109.4 (2)O3D—C17D—H17K109.5
O3B—C17B—H17D109.5H17J—C17D—H17K109.5
O3B—C17B—H17E109.5O3D—C17D—H17L109.5
H17D—C17B—H17E109.5H17J—C17D—H17L109.5
O3B—C17B—H17F109.5H17K—C17D—H17L109.5
H17D—C17B—H17F109.5O4D—C18D—H18M109.5
H17E—C17B—H17F109.5O4D—C18D—H18N109.5
O4B—C18B—H18G109.5H18M—C18D—H18N109.5
O4B—C18B—H18H109.5O4D—C18D—H18O109.5
H18G—C18B—H18H109.5H18M—C18D—H18O109.5
O4B—C18B—H18I109.5H18N—C18D—H18O109.5
H18G—C18B—H18I109.5O5D—C19D—H19J109.5
H18H—C18B—H18I109.5O5D—C19D—H19K109.5
O5B—C19B—H19D109.5H19J—C19D—H19K109.5
O5B—C19B—H19E109.5O5D—C19D—H19L109.5
H19D—C19B—H19E109.5H19J—C19D—H19L109.5
O5B—C19B—H19F109.5H19K—C19D—H19L109.5
C9A—N1A—C1A—O2A179.4 (2)C9B—N1B—C16B—C11B0.9 (3)
C16A—N1A—C1A—O2A1.8 (4)C9C—N1C—C1C—O2C175.8 (2)
C9A—N1A—C1A—C2A2.5 (3)C16C—N1C—C1C—O2C2.4 (4)
C16A—N1A—C1A—C2A176.3 (2)C9C—N1C—C1C—C2C4.2 (3)
O2A—C1A—C2A—C3A1.8 (4)C16C—N1C—C1C—C2C177.6 (2)
N1A—C1A—C2A—C3A176.3 (2)O2C—C1C—C2C—C3C1.2 (4)
O2A—C1A—C2A—C7A180.0 (2)N1C—C1C—C2C—C3C178.8 (2)
N1A—C1A—C2A—C7A1.9 (3)O2C—C1C—C2C—C7C178.2 (2)
C7A—C2A—C3A—C4A1.2 (4)N1C—C1C—C2C—C7C1.8 (3)
C1A—C2A—C3A—C4A177.0 (2)C7C—C2C—C3C—C4C0.3 (4)
C17A—O3A—C4A—C3A4.5 (4)C1C—C2C—C3C—C4C179.6 (2)
C17A—O3A—C4A—C5A175.5 (2)C17C—O3C—C4C—C3C2.9 (4)
C2A—C3A—C4A—O3A179.0 (2)C17C—O3C—C4C—C5C177.7 (2)
C2A—C3A—C4A—C5A1.0 (4)C2C—C3C—C4C—O3C179.7 (2)
C18E—O4A—C5A—C6A105 (2)C2C—C3C—C4C—C5C0.9 (4)
C18A—O4A—C5A—C6A70.4 (10)C18C—O4C—C5C—C6C88.5 (4)
C18E—O4A—C5A—C4A79 (2)C18C—O4C—C5C—C4C94.0 (3)
C18A—O4A—C5A—C4A114.1 (10)O3C—C4C—C5C—O4C1.7 (4)
O3A—C4A—C5A—O4A4.6 (3)C3C—C4C—C5C—O4C178.8 (2)
C3A—C4A—C5A—O4A175.5 (2)O3C—C4C—C5C—C6C179.2 (2)
O3A—C4A—C5A—C6A179.8 (2)C3C—C4C—C5C—C6C1.3 (4)
C3A—C4A—C5A—C6A0.2 (4)C19C—O5C—C6C—C5C55.0 (4)
C19A—O5A—C6A—C5A73.6 (3)C19C—O5C—C6C—C7C129.0 (3)
C19A—O5A—C6A—C7A108.2 (3)O4C—C5C—C6C—O5C6.3 (4)
O4A—C5A—C6A—O5A7.6 (4)C4C—C5C—C6C—O5C176.3 (2)
C4A—C5A—C6A—O5A176.9 (2)O4C—C5C—C6C—C7C177.9 (2)
O4A—C5A—C6A—C7A174.3 (2)C4C—C5C—C6C—C7C0.5 (4)
C4A—C5A—C6A—C7A1.2 (4)C3C—C2C—C7C—C6C1.1 (4)
C3A—C2A—C7A—C6A0.2 (3)C1C—C2C—C7C—C6C179.6 (2)
C1A—C2A—C7A—C6A178.0 (2)C3C—C2C—C7C—C8C178.2 (2)
C3A—C2A—C7A—C8A178.1 (2)C1C—C2C—C7C—C8C1.1 (3)
C1A—C2A—C7A—C8A0.1 (3)O5C—C6C—C7C—C2C175.4 (2)
O5A—C6A—C7A—C2A177.2 (2)C5C—C6C—C7C—C2C0.7 (4)
C5A—C6A—C7A—C2A1.0 (3)O5C—C6C—C7C—C8C5.3 (4)
O5A—C6A—C7A—C8A5.0 (3)C5C—C6C—C7C—C8C178.6 (2)
C5A—C6A—C7A—C8A176.8 (2)C2C—C7C—C8C—C9C1.9 (4)
C2A—C7A—C8A—C9A1.4 (4)C6C—C7C—C8C—C9C178.8 (2)
C6A—C7A—C8A—C9A176.4 (2)C7C—C8C—C9C—N1C0.3 (4)
C7A—C8A—C9A—N1A0.9 (4)C7C—C8C—C9C—C10C179.4 (2)
C7A—C8A—C9A—C10A177.5 (2)C1C—N1C—C9C—C8C3.6 (4)
C1A—N1A—C9A—C8A1.1 (4)C16C—N1C—C9C—C8C177.9 (2)
C16A—N1A—C9A—C8A177.8 (2)C1C—N1C—C9C—C10C176.1 (2)
C1A—N1A—C9A—C10A179.8 (2)C16C—N1C—C9C—C10C2.3 (3)
C16A—N1A—C9A—C10A0.9 (2)C8C—C9C—C10C—O1C2.0 (5)
C8A—C9A—C10A—O1A0.7 (5)N1C—C9C—C10C—O1C177.7 (3)
N1A—C9A—C10A—O1A179.2 (2)C8C—C9C—C10C—C11C178.4 (3)
C8A—C9A—C10A—C11A177.7 (3)N1C—C9C—C10C—C11C1.9 (3)
N1A—C9A—C10A—C11A0.9 (3)O1C—C10C—C11C—C16C178.8 (3)
O1A—C10A—C11A—C12A0.9 (5)C9C—C10C—C11C—C16C0.7 (3)
C9A—C10A—C11A—C12A177.4 (3)O1C—C10C—C11C—C12C1.9 (5)
O1A—C10A—C11A—C16A178.9 (3)C9C—C10C—C11C—C12C178.6 (3)
C9A—C10A—C11A—C16A0.5 (3)C16C—C11C—C12C—C13C0.4 (4)
C16A—C11A—C12A—C13A0.4 (4)C10C—C11C—C12C—C13C179.6 (3)
C10A—C11A—C12A—C13A177.4 (3)C11C—C12C—C13C—C14C0.7 (4)
C11A—C12A—C13A—C14A0.4 (4)C12C—C13C—C14C—C15C0.4 (5)
C12A—C13A—C14A—C15A0.2 (5)C13C—C14C—C15C—C16C0.1 (4)
C13A—C14A—C15A—C16A0.8 (4)C14C—C15C—C16C—C11C0.4 (4)
C14A—C15A—C16A—C11A0.8 (4)C14C—C15C—C16C—N1C179.7 (2)
C14A—C15A—C16A—N1A177.3 (2)C12C—C11C—C16C—C15C0.1 (4)
C12A—C11A—C16A—C15A0.3 (4)C10C—C11C—C16C—C15C179.3 (2)
C10A—C11A—C16A—C15A178.5 (2)C12C—C11C—C16C—N1C179.9 (2)
C12A—C11A—C16A—N1A178.2 (2)C10C—C11C—C16C—N1C0.7 (3)
C10A—C11A—C16A—N1A0.0 (3)C1C—N1C—C16C—C15C3.6 (4)
C1A—N1A—C16A—C15A1.2 (4)C9C—N1C—C16C—C15C178.0 (3)
C9A—N1A—C16A—C15A177.8 (2)C1C—N1C—C16C—C11C176.5 (2)
C1A—N1A—C16A—C11A179.5 (2)C9C—N1C—C16C—C11C1.9 (3)
C9A—N1A—C16A—C11A0.5 (3)C9D—N1D—C1D—O2D179.4 (2)
C9B—N1B—C1B—O2B179.6 (2)C16D—N1D—C1D—O2D1.2 (4)
C16B—N1B—C1B—O2B0.3 (4)C9D—N1D—C1D—C2D0.7 (3)
C9B—N1B—C1B—C2B0.8 (3)C16D—N1D—C1D—C2D179.0 (2)
C16B—N1B—C1B—C2B179.2 (2)O2D—C1D—C2D—C3D3.4 (4)
O2B—C1B—C2B—C3B0.2 (4)N1D—C1D—C2D—C3D176.8 (2)
N1B—C1B—C2B—C3B179.0 (2)O2D—C1D—C2D—C7D177.8 (2)
O2B—C1B—C2B—C7B179.0 (2)N1D—C1D—C2D—C7D2.1 (3)
N1B—C1B—C2B—C7B0.2 (3)C7D—C2D—C3D—C4D1.2 (4)
C7B—C2B—C3B—C4B0.2 (4)C1D—C2D—C3D—C4D179.9 (2)
C1B—C2B—C3B—C4B178.9 (2)C17D—O3D—C4D—C3D11.0 (4)
C17B—O3B—C4B—C3B2.5 (4)C17D—O3D—C4D—C5D168.9 (2)
C17B—O3B—C4B—C5B177.7 (2)C2D—C3D—C4D—O3D178.3 (2)
C2B—C3B—C4B—O3B179.8 (2)C2D—C3D—C4D—C5D1.5 (4)
C2B—C3B—C4B—C5B0.0 (4)C18D—O4D—C5D—C6D86.3 (3)
C18B—O4B—C5B—C6B69.3 (3)C18D—O4D—C5D—C4D97.3 (3)
C18B—O4B—C5B—C4B113.0 (3)O3D—C4D—C5D—O4D0.6 (3)
O3B—C4B—C5B—O4B2.2 (3)C3D—C4D—C5D—O4D179.3 (2)
C3B—C4B—C5B—O4B178.0 (2)O3D—C4D—C5D—C6D177.0 (2)
O3B—C4B—C5B—C6B179.9 (2)C3D—C4D—C5D—C6D2.9 (4)
C3B—C4B—C5B—C6B0.3 (4)C19D—O5D—C6D—C5D62.0 (3)
C19B—O5B—C6B—C5B64.1 (3)C19D—O5D—C6D—C7D120.9 (2)
C19B—O5B—C6B—C7B118.7 (3)O4D—C5D—C6D—O5D5.3 (4)
O4B—C5B—C6B—O5B4.5 (4)C4D—C5D—C6D—O5D178.4 (2)
C4B—C5B—C6B—O5B177.8 (2)O4D—C5D—C6D—C7D177.7 (2)
O4B—C5B—C6B—C7B178.4 (2)C4D—C5D—C6D—C7D1.4 (4)
C4B—C5B—C6B—C7B0.7 (4)C3D—C2D—C7D—C6D2.6 (3)
O5B—C6B—C7B—C2B178.1 (2)C1D—C2D—C7D—C6D178.6 (2)
C5B—C6B—C7B—C2B0.9 (4)C3D—C2D—C7D—C8D175.9 (2)
O5B—C6B—C7B—C8B2.8 (3)C1D—C2D—C7D—C8D3.0 (3)
C5B—C6B—C7B—C8B180.0 (2)O5D—C6D—C7D—C2D175.9 (2)
C3B—C2B—C7B—C6B0.7 (3)C5D—C6D—C7D—C2D1.3 (3)
C1B—C2B—C7B—C6B178.5 (2)O5D—C6D—C7D—C8D5.7 (3)
C3B—C2B—C7B—C8B179.8 (2)C5D—C6D—C7D—C8D177.1 (2)
C1B—C2B—C7B—C8B0.7 (3)C2D—C7D—C8D—C9D0.9 (4)
C6B—C7B—C8B—C9B178.2 (2)C6D—C7D—C8D—C9D179.3 (2)
C2B—C7B—C8B—C9B0.9 (4)C7D—C8D—C9D—N1D2.0 (4)
C7B—C8B—C9B—N1B0.4 (4)C7D—C8D—C9D—C10D177.4 (2)
C7B—C8B—C9B—C10B178.9 (2)C1D—N1D—C9D—C8D2.9 (4)
C1B—N1B—C9B—C8B0.5 (4)C16D—N1D—C9D—C8D178.6 (2)
C16B—N1B—C9B—C8B179.5 (2)C1D—N1D—C9D—C10D176.6 (2)
C1B—N1B—C9B—C10B179.9 (2)C16D—N1D—C9D—C10D1.9 (3)
C16B—N1B—C9B—C10B0.0 (3)C8D—C9D—C10D—O1D2.0 (5)
C8B—C9B—C10B—O1B1.4 (5)N1D—C9D—C10D—O1D177.4 (3)
N1B—C9B—C10B—O1B179.2 (3)C8D—C9D—C10D—C11D179.3 (3)
C8B—C9B—C10B—C11B178.6 (3)N1D—C9D—C10D—C11D1.3 (3)
N1B—C9B—C10B—C11B0.7 (3)O1D—C10D—C11D—C12D1.7 (6)
O1B—C10B—C11B—C12B1.0 (5)C9D—C10D—C11D—C12D179.6 (3)
C9B—C10B—C11B—C12B179.0 (3)O1D—C10D—C11D—C16D178.5 (3)
O1B—C10B—C11B—C16B178.7 (3)C9D—C10D—C11D—C16D0.2 (3)
C9B—C10B—C11B—C16B1.3 (3)C16D—C11D—C12D—C13D1.6 (5)
C16B—C11B—C12B—C13B1.2 (5)C10D—C11D—C12D—C13D178.1 (3)
C10B—C11B—C12B—C13B178.5 (3)C11D—C12D—C13D—C14D0.7 (5)
C11B—C12B—C13B—C14B0.8 (5)C12D—C13D—C14D—C15D0.3 (5)
C12B—C13B—C14B—C15B0.5 (5)C13D—C14D—C15D—C16D0.3 (5)
C13B—C14B—C15B—C16B1.3 (5)C14D—C15D—C16D—C11D0.7 (4)
C14B—C15B—C16B—C11B0.9 (4)C14D—C15D—C16D—N1D179.6 (3)
C14B—C15B—C16B—N1B180.0 (3)C12D—C11D—C16D—C15D1.7 (4)
C12B—C11B—C16B—C15B0.4 (4)C10D—C11D—C16D—C15D178.1 (3)
C10B—C11B—C16B—C15B179.4 (2)C12D—C11D—C16D—N1D179.2 (3)
C12B—C11B—C16B—N1B178.9 (3)C10D—C11D—C16D—N1D1.0 (3)
C10B—C11B—C16B—N1B1.3 (3)C1D—N1D—C16D—C15D4.4 (4)
C1B—N1B—C16B—C15B0.1 (4)C9D—N1D—C16D—C15D177.2 (3)
C9B—N1B—C16B—C15B179.9 (3)C1D—N1D—C16D—C11D176.6 (2)
C1B—N1B—C16B—C11B179.1 (2)C9D—N1D—C16D—C11D1.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15A—H15A···O2A0.932.392.926 (3)116
C15B—H15B···O2B0.932.412.939 (4)116
C15C—H15C···O2C0.932.402.929 (3)116
C15D—H15D···O2D0.932.382.920 (4)117
C18A—H18C···O5A0.962.493.053 (17)117
C18B—H18I···O5B0.962.503.109 (4)121
C19A—H19C···O4A0.962.553.096 (4)117
C19B—H19F···O4B0.962.383.026 (4)124
C19C—H19G···O4C0.962.502.919 (5)106
C19D—H19J···O4D0.962.342.981 (4)123
C18D—H18N···O5A0.962.543.439 (4)156
C18D—H18O···O1C0.962.603.372 (4)138
C19D—H19K···O1A0.962.573.502 (4)164
C12A—H12A···O1Ci0.932.563.345 (3)142
C14B—H14B···O2Cii0.932.353.254 (4)162
C14D—H14D···O2Aiii0.932.533.201 (4)129
C17C—H17H···O3Aiv0.962.563.451 (4)154
C17D—H17K···O3Bv0.962.513.298 (4)140
C18A—H18A···O1Bvi0.962.323.278 (16)173
C18B—H18G···O1Avii0.962.383.264 (4)153
C18B—H18H···O5Cvii0.962.503.420 (4)160
C19A—H19A···O2Bviii0.962.423.373 (4)175
C19B—H19D···O2Aix0.962.333.240 (4)158
C19C—H19I···O2Dii0.962.333.252 (5)162
C19D—H19L···O2Cx0.962.383.312 (4)164
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y+1/2, z+1/2; (v) x, y+1, z; (vi) x, y1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x, y1, z; (ix) x, y+1, z; (x) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H15NO5
Mr337.32
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)20.8934 (4), 14.2400 (3), 22.8886 (4)
β (°) 110.014 (1)
V3)6398.6 (2)
Z16
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.44 × 0.34 × 0.20
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Siemens, 1996)
Tmin, Tmax0.739, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
40492, 15541, 7962
Rint0.048
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.210, 1.09
No. of reflections15541
No. of parameters924
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.18

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ZORTEP (Zsolnai, 1997) and PLATON (Spek, 2003), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) top
O1A—C10A1.221 (3)O1C—C10C1.215 (3)
O2A—C1A1.220 (3)O2C—C1C1.225 (3)
N1A—C1A1.381 (3)N1C—C1C1.378 (3)
N1A—C9A1.407 (3)N1C—C9C1.407 (3)
N1A—C16A1.425 (3)N1C—C16C1.422 (3)
C8A—C9A1.350 (3)C8C—C9C1.332 (3)
O1B—C10B1.220 (3)O1D—C10D1.221 (3)
O2B—C1B1.229 (3)O2D—C1D1.220 (3)
N1B—C1B1.385 (3)N1D—C1D1.395 (3)
N1B—C9B1.412 (3)N1D—C9D1.403 (3)
N1B—C16B1.414 (3)N1D—C16D1.422 (3)
C8B—C9B1.337 (3)C8D—C9D1.335 (3)
C1A—N1A—C9A123.9 (2)C1C—N1C—C9C123.5 (2)
C1A—N1A—C16A126.8 (2)C1C—N1C—C16C127.0 (2)
C9A—N1A—C16A109.2 (2)C9C—N1C—C16C109.6 (2)
C8A—C9A—C10A131.1 (2)C8C—C9C—C10C131.2 (2)
C1B—N1B—C9B123.2 (2)C1D—N1D—C9D123.3 (2)
C1B—N1B—C16B127.2 (2)C1D—N1D—C16D126.8 (2)
C9B—N1B—C16B109.6 (2)C9D—N1D—C16D109.9 (2)
C8B—C9B—C10B131.4 (2)C8D—C9D—C10D130.8 (2)
C17A—O3A—C4A—C3A4.5 (4)C17C—O3C—C4C—C3C2.9 (4)
C18E—O4A—C5A—C6A105 (2)C18C—O4C—C5C—C6C88.5 (4)
C18A—O4A—C5A—C6A70.4 (10)C19C—O5C—C6C—C5C55.0 (4)
C19A—O5A—C6A—C5A73.6 (3)C17D—O3D—C4D—C3D11.0 (4)
C17B—O3B—C4B—C3B2.5 (4)C18D—O4D—C5D—C6D86.3 (3)
C18B—O4B—C5B—C6B69.3 (3)C19D—O5D—C6D—C5D62.0 (3)
C19B—O5B—C6B—C5B64.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C15A—H15A···O2A0.932.392.926 (3)116
C15B—H15B···O2B0.932.412.939 (4)116
C15C—H15C···O2C0.932.402.929 (3)116
C15D—H15D···O2D0.932.382.920 (4)117
C18A—H18C···O5A0.962.493.053 (17)117
C18B—H18I···O5B0.962.503.109 (4)121
C19A—H19C···O4A0.962.553.096 (4)117
C19B—H19F···O4B0.962.383.026 (4)124
C19C—H19G···O4C0.962.502.919 (5)106
C19D—H19J···O4D0.962.342.981 (4)123
C18D—H18N···O5A0.962.543.439 (4)156
C18D—H18O···O1C0.962.603.372 (4)138
C19D—H19K···O1A0.962.573.502 (4)164
C12A—H12A···O1Ci0.932.563.345 (3)142
C14B—H14B···O2Cii0.932.353.254 (4)162
C14D—H14D···O2Aiii0.932.533.201 (4)129
C17C—H17H···O3Aiv0.962.563.451 (4)154
C17D—H17K···O3Bv0.962.513.298 (4)140
C18A—H18A···O1Bvi0.962.323.278 (16)173
C18B—H18G···O1Avii0.962.383.264 (4)153
C18B—H18H···O5Cvii0.962.503.420 (4)160
C19A—H19A···O2Bviii0.962.423.373 (4)175
C19B—H19D···O2Aix0.962.333.240 (4)158
C19C—H19I···O2Dii0.962.333.252 (5)162
C19D—H19L···O2Cx0.962.383.312 (4)164
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+1, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+1, y+1/2, z+1/2; (v) x, y+1, z; (vi) x, y1/2, z+1/2; (vii) x, y+1/2, z+1/2; (viii) x, y1, z; (ix) x, y+1, z; (x) x+1, y1/2, z+1/2.
 

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