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In the title compound, 8-oxotetra­hydro­thalifendine, C19H17NO5, the di­hydro­pyrido and pyrido moieties adopt the intermediate conformations of envelope–screw-boat and envelope–twist, respectively. The dihedral angle between the two benzene rings is 37.16 (8)°. In the crystal structure, the mol­ecules translated by a unit along the c axis are linked by three weak C—H...O intermolecular interactions to form a molecular chain. Along the a axis, the adjacent chains related by screw symmetry are connected by a strong O—H...O and a weak C—H...O intermolecular interaction to form layers parallel to the bc plane.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012327/ac6043sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012327/ac6043Isup2.hkl
Contains datablock I

CCDC reference: 217439

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.052
  • wR factor = 0.113
  • Data-to-parameter ratio = 7.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes

REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.00 From the CIF: _reflns_number_total 2104 Count of symmetry unique reflns 2136 Completeness (_total/calc) 98.50% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.

Comment top

Protoberberine alkaloids found in many plants exhibit pharmacological activities (Schmeller & Wink, 1998; Simeon et al., 1989). The crystal structures of berberine salts [chloride, bromide, iodide, sulfate, hydrogen sulfate, azide, thiocyanate (Abadi et al., 1984; Kariuki & Jones, 1995; Man et al., 2001], jatrorrhizine (Ghosh et al., 1993), 8-cyano-8H-berberine (Man et al., 2001), isocorypalmine (Ribar et al., 1992), canadine (Sakai & Taira, 1987) and capaurine (Shimanouchi et al., 1969) have been reported. In the present study, the structure of 8-oxotetrahydrothalifendine (10-hydroxy-9-methoxy-5,6,13,13a-tetrahydro -[1,3]dioxolo[4,5-g] isoquino[3,2-a]isoquinolin-8-one), (I), has been investigated.

The molecular structure of (I), with the atomic numbering scheme, is shown in Fig. 1. The dihydropyrido moiety adopts an intermediate form between envelope and screw boat conformations, with puckering parameters Q, θ and ϕ (Cremer & Pople, 1975) of 0.511 Å, 116.1 and 250.8°, respectively. The pyrido moiety exhibits an intermediate form between envelope and twist conformations, with the corresponding values of 0.513 Å, 67.3 and 276.4°, respectively. The dioxolane ring is in an envelope form, with Q of 0.119 Å and ϕ of 143.4°. The dihedral angle between the least-squares planes through the two benzo rings is 37.16°, which is comparable to those of isocorypalmine (33.81°; Ribar et al., 1992) and of 8-cyano-8H-berberine (37.69°; Man et al., 2001). This is much higher than those of the other above-mentioned berberine structures (range 4.24–14.96°). The methoxy group at C9 is nearly perpendicular to the benzo ring, with a torsion angle C10–C9–O19–C15 of −86.1 (3)°.

In the crystal structure, the molecules translated by a unit along the c axis are linked by weak C14–H14B···O19iii, C14–H14B···O20iii [symmetry code: (iii) x, y, z − 1] and C15–H15C···O17iv [symmetry code: (iv) x, y, 1 + z] interactions to form a molecular chain (Fig. 2 and Table 2). Along the a axis, adjacent chains related by screw symmetry are connected by a strong O20–H20···O18i [symmetry code: (i) −x, 1/2 + y, 3/2 − z] and a weak C5–H5B···O16ii [symmetry code: (ii) −x, y − 1/2, 1/2 − z] hydrogen bond to form layers (Fig. 2) parallel to the bc plane.

Experimental top

The title compound was isolated from the stems of Coscinium fenestratum. Crystals were obtained by recrystallizing the ethyl acetate/dichloromethane crude extract from a solvent mixture of dichloromethane/methanol. M.p. 481–483 K. The 1H and 13C NMR results confirmed that the title compound is 8-oxotetrahydrothalifendine as previously reported (Pinho et al., 1992; Gentry et al., 1998).

Refinement top

The Friedel pairs were merged during the refinement. The absolute configuration could not be determined, thus an arbitrary chioce of enantiomers has been made. All H atoms were located from a difference Fourier map and both positional and isotropic displacement parameters were refined except for H14A; as the C14–H14A bond is too long (1.24 Å), it is restrained to a reasonable distance of 1.09 Å. The ranges of C–H and O–H bond lengths are 0.88 (4)–1.03 (3) and 0.88 (4) Å, respectively.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Bruker, 2000) and SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and MOLSCRIPT (Kraulis, 1991); software used to prepare material for publication: PLATON (Spek, 1990) and SHELXL97.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Packing diagram of the title compound, viewed down the a axis. The molecular layers in the front and in the back as gray and white, respectively.
10-Hydroxy-9-methoxy-5,6,13,13a-tetrahydro-[1,3]dioxolo[4,5-g] isoquino[3,2-a]isoquinolin-8-one top
Crystal data top
C19H17NO5Dx = 1.458 Mg m3
Mr = 339.34Melting point: 481–483 K K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 1481 reflections
a = 8.0217 (7) Åθ = 2.5–20.4°
b = 13.5313 (12) ŵ = 0.11 mm1
c = 14.2383 (12) ÅT = 295 K
V = 1545.5 (2) Å3Rod, colorless
Z = 40.16 × 0.11 × 0.09 mm
F(000) = 712
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2104 independent reflections
Radiation source: fine-focus sealed tube1771 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω–scansθmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
h = 1010
Tmin = 0.986, Tmax = 0.991k = 1317
9913 measured reflectionsl = 1718
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.0546P)2 + 0.153P]
where P = (Fo2 + 2Fc2)/3
2104 reflections(Δ/σ)max = 0.001
294 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.33 e Å3
Crystal data top
C19H17NO5V = 1545.5 (2) Å3
Mr = 339.34Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.0217 (7) ŵ = 0.11 mm1
b = 13.5313 (12) ÅT = 295 K
c = 14.2383 (12) Å0.16 × 0.11 × 0.09 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2104 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1771 reflections with I > 2σ(I)
Tmin = 0.986, Tmax = 0.991Rint = 0.041
9913 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0531 restraint
wR(F2) = 0.113H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.24 e Å3
2104 reflectionsΔρmin = 0.33 e Å3
294 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*/Ueq
C10.1012 (4)0.4201 (2)0.25512 (19)0.0366 (7)
C20.0828 (4)0.4013 (2)0.1609 (2)0.0401 (7)
C30.0009 (5)0.3188 (2)0.12944 (19)0.0409 (7)
C40.0693 (4)0.2518 (2)0.1894 (2)0.0427 (8)
C4A0.0529 (4)0.2691 (2)0.28624 (19)0.0339 (6)
C50.1155 (5)0.1950 (3)0.3559 (2)0.0450 (8)
C60.0087 (5)0.1959 (2)0.4430 (2)0.0381 (7)
N70.0080 (4)0.29493 (16)0.48346 (15)0.0328 (6)
C80.0408 (4)0.30775 (19)0.57583 (17)0.0285 (6)
C8A0.0432 (4)0.41180 (19)0.61218 (18)0.0290 (6)
C90.0277 (4)0.43288 (18)0.70804 (18)0.0295 (6)
C100.0348 (4)0.5311 (2)0.73873 (18)0.0349 (7)
C110.0627 (4)0.6058 (2)0.6755 (2)0.0410 (7)
C120.0776 (4)0.5851 (2)0.5808 (2)0.0416 (8)
C12A0.0649 (4)0.48938 (19)0.54857 (18)0.0319 (6)
C130.0741 (4)0.4653 (2)0.4449 (2)0.0352 (7)
C13A0.0398 (4)0.37858 (19)0.42215 (18)0.0296 (6)
C13B0.0291 (4)0.3525 (2)0.31851 (18)0.0315 (6)
C140.1097 (9)0.3956 (4)0.0064 (3)0.0820 (18)
C150.1564 (5)0.3299 (3)0.8167 (2)0.0476 (9)
O160.1411 (4)0.45540 (17)0.08607 (14)0.0568 (7)
O170.0007 (4)0.31739 (17)0.03245 (14)0.0600 (7)
O180.0706 (3)0.23673 (14)0.62793 (13)0.0401 (5)
O190.0021 (3)0.36075 (14)0.77491 (12)0.0356 (5)
O200.0131 (3)0.54781 (16)0.83272 (13)0.0437 (6)
H10.164 (4)0.478 (2)0.2751 (19)0.029 (7)*
H40.120 (4)0.197 (3)0.165 (2)0.040 (9)*
H5A0.229 (6)0.208 (3)0.372 (3)0.072 (13)*
H5B0.125 (5)0.134 (3)0.328 (2)0.064 (11)*
H6A0.054 (5)0.156 (3)0.493 (2)0.059 (11)*
H6B0.111 (4)0.176 (2)0.425 (2)0.038 (8)*
H110.081 (4)0.669 (2)0.693 (2)0.042 (9)*
H120.099 (5)0.633 (3)0.538 (2)0.051 (10)*
H13A0.044 (4)0.520 (2)0.4066 (18)0.030 (7)*
H13B0.189 (4)0.446 (2)0.4262 (19)0.030 (8)*
H13'0.154 (3)0.3986 (19)0.4376 (16)0.015 (6)*
H14A0.232 (10)0.362 (6)0.006 (6)0.24 (4)*
H14B0.077 (5)0.428 (3)0.044 (3)0.060 (11)*
H15A0.223 (5)0.294 (3)0.770 (3)0.072 (12)*
H15B0.214 (5)0.385 (3)0.847 (2)0.060 (11)*
H15C0.126 (6)0.282 (3)0.863 (3)0.080 (13)*
H200.012 (5)0.611 (3)0.835 (2)0.060 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0494 (19)0.0290 (15)0.0315 (14)0.0027 (14)0.0028 (13)0.0002 (12)
C20.056 (2)0.0329 (16)0.0318 (14)0.0008 (15)0.0013 (14)0.0065 (12)
C30.058 (2)0.0366 (16)0.0285 (13)0.0087 (16)0.0070 (14)0.0032 (12)
C40.055 (2)0.0333 (16)0.0395 (16)0.0035 (16)0.0097 (15)0.0051 (13)
C4A0.0383 (17)0.0300 (14)0.0332 (14)0.0008 (12)0.0018 (13)0.0024 (12)
C50.062 (2)0.0404 (19)0.0323 (16)0.0168 (17)0.0020 (16)0.0045 (14)
C60.059 (2)0.0228 (13)0.0322 (14)0.0002 (14)0.0062 (15)0.0002 (12)
N70.0473 (15)0.0216 (11)0.0294 (11)0.0001 (11)0.0001 (11)0.0021 (9)
C80.0363 (16)0.0239 (12)0.0253 (12)0.0014 (12)0.0039 (12)0.0019 (11)
C8A0.0319 (16)0.0241 (12)0.0309 (13)0.0002 (12)0.0010 (11)0.0005 (10)
C90.0321 (15)0.0251 (13)0.0314 (13)0.0001 (11)0.0012 (12)0.0020 (11)
C100.0422 (18)0.0331 (15)0.0295 (13)0.0012 (14)0.0027 (13)0.0027 (12)
C110.057 (2)0.0232 (15)0.0425 (17)0.0044 (15)0.0025 (15)0.0042 (12)
C120.058 (2)0.0264 (14)0.0404 (16)0.0091 (14)0.0001 (16)0.0069 (13)
C12A0.0397 (17)0.0258 (13)0.0303 (13)0.0042 (12)0.0030 (12)0.0004 (11)
C130.049 (2)0.0281 (14)0.0281 (13)0.0057 (14)0.0043 (13)0.0051 (12)
C13A0.0365 (17)0.0234 (13)0.0290 (13)0.0032 (12)0.0018 (12)0.0034 (11)
C13B0.0383 (17)0.0285 (13)0.0276 (13)0.0017 (13)0.0021 (12)0.0020 (11)
C140.157 (6)0.063 (3)0.0262 (18)0.028 (3)0.003 (2)0.0057 (18)
C150.067 (2)0.0371 (19)0.0386 (18)0.0059 (17)0.0133 (17)0.0024 (15)
O160.095 (2)0.0457 (13)0.0295 (11)0.0067 (14)0.0076 (13)0.0022 (10)
O170.102 (2)0.0511 (14)0.0267 (11)0.0040 (16)0.0055 (12)0.0022 (9)
O180.0638 (15)0.0235 (10)0.0330 (10)0.0026 (10)0.0043 (10)0.0031 (8)
O190.0479 (12)0.0280 (10)0.0307 (9)0.0007 (10)0.0013 (10)0.0051 (8)
O200.0716 (16)0.0294 (11)0.0303 (10)0.0066 (12)0.0016 (11)0.0045 (9)
Geometric parameters (Å, º) top
C1—C21.374 (4)C9—O191.379 (3)
C1—C13B1.408 (4)C9—C101.400 (4)
C1—H10.98 (3)C10—O201.368 (3)
C2—O161.375 (4)C10—C111.372 (4)
C2—C31.377 (4)C11—C121.383 (4)
C3—C41.361 (5)C11—H110.91 (3)
C3—O171.381 (3)C12—C12A1.377 (4)
C4—C4A1.404 (4)C12—H120.90 (3)
C4—H40.91 (3)C12A—C131.514 (4)
C4A—C13B1.385 (4)C13—C13A1.522 (4)
C4A—C51.497 (4)C13—H13A0.95 (3)
C5—C61.508 (5)C13—H13B0.99 (3)
C5—H5A0.95 (5)C13A—C13B1.519 (4)
C5—H5B0.91 (4)C13A—H13'0.98 (3)
C6—N71.459 (3)C14—O161.415 (5)
C6—H6A0.96 (4)C14—O171.422 (5)
C6—H6B1.03 (3)C14—H14A1.09 (7)
N7—C81.352 (3)C14—H14B0.88 (4)
N7—C13A1.480 (3)C15—O191.436 (4)
C8—O181.237 (3)C15—H15A0.98 (4)
C8—C8A1.500 (3)C15—H15B0.98 (4)
C8A—C12A1.397 (4)C15—H15C0.96 (4)
C8A—C91.400 (4)O20—H200.88 (4)
C2—C1—C13B117.5 (3)C11—C10—C9120.1 (2)
C2—C1—H1119.3 (17)C10—C11—C12120.3 (3)
C13B—C1—H1123.2 (16)C10—C11—H11123 (2)
C1—C2—O16128.4 (3)C12—C11—H11117 (2)
C1—C2—C3121.3 (3)C12A—C12—C11120.6 (3)
O16—C2—C3110.2 (2)C12A—C12—H12117 (2)
C4—C3—C2122.2 (3)C11—C12—H12122 (2)
C4—C3—O17128.5 (3)C12—C12A—C8A120.0 (3)
C2—C3—O17109.4 (3)C12—C12A—C13121.6 (3)
C3—C4—C4A117.8 (3)C8A—C12A—C13118.5 (2)
C3—C4—H4118.7 (19)C12A—C13—C13A110.1 (2)
C4A—C4—H4123.4 (19)C12A—C13—H13A112.4 (16)
C13B—C4A—C4120.4 (3)C13A—C13—H13A108.8 (18)
C13B—C4A—C5119.1 (2)C12A—C13—H13B111.3 (16)
C4—C4A—C5120.4 (3)C13A—C13—H13B107.4 (16)
C4A—C5—C6110.4 (3)H13A—C13—H13B107 (2)
C4A—C5—H5A111 (2)N7—C13A—C13B112.4 (2)
C6—C5—H5A110 (2)N7—C13A—C13108.0 (2)
C4A—C5—H5B110 (2)C13B—C13A—C13110.6 (2)
C6—C5—H5B114 (2)N7—C13A—H13'108.7 (15)
H5A—C5—H5B101 (3)C13B—C13A—H13'109.5 (14)
N7—C6—C5109.5 (3)C13—C13A—H13'107.6 (15)
N7—C6—H6A103 (2)C4A—C13B—C1120.7 (2)
C5—C6—H6A113 (2)C4A—C13B—C13A122.5 (2)
N7—C6—H6B109.6 (17)C1—C13B—C13A116.7 (3)
C5—C6—H6B109.0 (17)O16—C14—O17109.0 (3)
H6A—C6—H6B113 (3)O16—C14—H14A102 (4)
C8—N7—C6120.1 (2)O17—C14—H14A107 (5)
C8—N7—C13A121.7 (2)O16—C14—H14B115 (2)
C6—N7—C13A118.1 (2)O17—C14—H14B114 (3)
O18—C8—N7121.4 (2)H14A—C14—H14B110 (5)
O18—C8—C8A121.3 (2)O19—C15—H15A110 (2)
N7—C8—C8A117.3 (2)O19—C15—H15B111 (2)
C12A—C8A—C9119.3 (2)H15A—C15—H15B115 (3)
C12A—C8A—C8118.9 (2)O19—C15—H15C105 (3)
C9—C8A—C8121.8 (2)H15A—C15—H15C105 (3)
O19—C9—C8A122.8 (2)H15B—C15—H15C109 (3)
O19—C9—C10117.5 (2)C2—O16—C14104.8 (3)
C8A—C9—C10119.6 (2)C3—O17—C14104.8 (3)
O20—C10—C11122.7 (3)C9—O19—C15111.3 (2)
O20—C10—C9117.2 (3)C10—O20—H20103 (2)
C13B—C1—C2—O16179.9 (3)C10—C11—C12—C12A0.1 (5)
C13B—C1—C2—C30.9 (5)C11—C12—C12A—C8A2.5 (5)
C1—C2—C3—C40.0 (5)C11—C12—C12A—C13177.6 (3)
O16—C2—C3—C4179.1 (3)C9—C8A—C12A—C122.6 (5)
C1—C2—C3—O17179.3 (3)C8—C8A—C12A—C12176.1 (3)
O16—C2—C3—O170.1 (4)C9—C8A—C12A—C13177.5 (3)
C2—C3—C4—C4A0.2 (5)C8—C8A—C12A—C133.8 (4)
O17—C3—C4—C4A179.3 (3)C12—C12A—C13—C13A145.6 (3)
C3—C4—C4A—C13B0.7 (5)C8A—C12A—C13—C13A34.5 (4)
C3—C4—C4A—C5176.0 (3)C8—N7—C13A—C13B165.9 (3)
C13B—C4A—C5—C628.7 (4)C6—N7—C13A—C13B18.0 (4)
C4—C4A—C5—C6148.1 (3)C8—N7—C13A—C1343.7 (4)
C4A—C5—C6—N757.7 (4)C6—N7—C13A—C13140.2 (3)
C5—C6—N7—C8129.9 (3)C12A—C13—C13A—N755.6 (3)
C5—C6—N7—C13A54.0 (4)C12A—C13—C13A—C13B179.0 (2)
C6—N7—C8—O180.5 (5)C4—C4A—C13B—C11.7 (5)
C13A—N7—C8—O18175.5 (3)C5—C4A—C13B—C1175.0 (3)
C6—N7—C8—C8A178.2 (3)C4—C4A—C13B—C13A175.5 (3)
C13A—N7—C8—C8A5.8 (4)C5—C4A—C13B—C13A7.7 (4)
O18—C8—C8A—C12A158.7 (3)C2—C1—C13B—C4A1.8 (5)
N7—C8—C8A—C12A20.0 (4)C2—C1—C13B—C13A175.6 (3)
O18—C8—C8A—C920.0 (5)N7—C13A—C13B—C4A14.2 (4)
N7—C8—C8A—C9161.3 (3)C13—C13A—C13B—C4A106.6 (3)
C12A—C8A—C9—O19178.4 (3)N7—C13A—C13B—C1168.4 (3)
C8—C8A—C9—O192.9 (5)C13—C13A—C13B—C170.8 (4)
C12A—C8A—C9—C100.2 (5)C1—C2—O16—C14171.3 (4)
C8—C8A—C9—C10178.4 (3)C3—C2—O16—C147.8 (5)
O19—C9—C10—O201.0 (4)O17—C14—O16—C212.8 (5)
C8A—C9—C10—O20177.7 (3)C4—C3—O17—C14171.2 (4)
O19—C9—C10—C11179.0 (3)C2—C3—O17—C148.0 (5)
C8A—C9—C10—C112.3 (5)O16—C14—O17—C312.9 (6)
O20—C10—C11—C12177.6 (3)C8A—C9—O19—C1595.2 (3)
C9—C10—C11—C122.5 (5)C10—C9—O19—C1586.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O18i0.88 (4)1.84 (4)2.702 (3)165 (3)
C5—H5B···O16ii0.91 (4)2.72 (4)3.352 (4)128 (3)
C14—H14B···O19iii0.88 (4)2.81 (4)3.449 (4)130 (3)
C14—H14B···O20iii0.88 (4)2.50 (4)3.366 (5)170 (3)
C15—H15C···O17iv0.96 (4)2.66 (4)3.325 (4)127 (3)
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x, y1/2, z+1/2; (iii) x, y, z1; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC19H17NO5
Mr339.34
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)8.0217 (7), 13.5313 (12), 14.2383 (12)
V3)1545.5 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.16 × 0.11 × 0.09
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.986, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
9913, 2104, 1771
Rint0.041
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.113, 1.12
No. of reflections2104
No. of parameters294
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.33

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Bruker, 2000) and SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and MOLSCRIPT (Kraulis, 1991), PLATON (Spek, 1990) and SHELXL97.

Selected bond lengths (Å) top
C2—O161.375 (4)C9—O191.379 (3)
C3—O171.381 (3)C10—O201.368 (3)
C6—N71.459 (3)C14—O161.415 (5)
N7—C81.352 (3)C14—O171.422 (5)
N7—C13A1.480 (3)C15—O191.436 (4)
C8—O181.237 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O20—H20···O18i0.88 (4)1.84 (4)2.702 (3)165 (3)
C5—H5B···O16ii0.91 (4)2.72 (4)3.352 (4)128 (3)
C14—H14B···O19iii0.88 (4)2.81 (4)3.449 (4)130 (3)
C14—H14B···O20iii0.88 (4)2.50 (4)3.366 (5)170 (3)
C15—H15C···O17iv0.96 (4)2.66 (4)3.325 (4)127 (3)
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x, y1/2, z+1/2; (iii) x, y, z1; (iv) x, y, z+1.
 

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