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The title compound [systematic name: 6,6a,11,12-tetra­hydro-8,9-dimeth­oxy-14H-dioxolo[4′,5′:7,8]isoquinolino[3,2-a]isoquinoline], also known as sinactine, C20H21NO4, a protoberberine-type alkaloid, was isolated from the roots of the plant Sinomenium acutum. Both piperidine rings adopt half-chair conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007471/ci2018sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007471/ci2018Isup2.hkl
Contains datablock I

CCDC reference: 605015

Key indicators

  • Single-crystal X-ray study
  • T = 288 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.086
  • Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.22 PLAT715_ALERT_1_C D-H Unknown or Inconsistent Label .......... TABLE H
Alert level G REFLT03_ALERT_4_G 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. From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 2277 Count of symmetry unique reflns 2277 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Tetrahydroepiberberine top
Crystal data top
C20H21NO4F(000) = 720
Mr = 339.38Dx = 1.320 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 32 reflections
a = 7.367 (1) Åθ = 2.5–16.8°
b = 8.377 (2) ŵ = 0.09 mm1
c = 27.676 (5) ÅT = 288 K
V = 1708.0 (6) Å3Block, colourless
Z = 40.58 × 0.46 × 0.38 mm
Data collection top
Siemens P4
diffractometer
Rint = 0.012
Radiation source: normal-focus sealed tubeθmax = 27.5°, θmin = 1.5°
Graphite monochromatorh = 09
ω scansk = 010
2472 measured reflectionsl = 135
2277 independent reflections3 standard reflections every 97 reflections
1530 reflections with I > 2σ(I) intensity decay: 1.6%
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)] = 0.038H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0426P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.95(Δ/σ)max = 0.001
2277 reflectionsΔρmax = 0.16 e Å3
229 parametersΔρmin = 0.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0166 (16)
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
O10.6784 (3)0.7657 (2)0.15622 (5)0.0749 (6)
O20.9505 (3)0.6819 (2)0.12331 (5)0.0707 (6)
O30.5821 (2)0.57957 (19)0.53883 (4)0.0504 (5)
O40.7091 (3)0.3350 (2)0.49434 (5)0.0600 (5)
N70.5788 (3)0.7426 (2)0.31223 (5)0.0414 (5)
C4A0.5293 (3)0.7193 (3)0.41238 (7)0.0374 (5)
C30.5826 (3)0.5912 (3)0.48953 (7)0.0388 (5)
C40.5187 (3)0.7168 (3)0.46326 (7)0.0422 (6)
H40.46670.80300.47930.051*
C13A0.6296 (3)0.5896 (3)0.33388 (7)0.0391 (6)
H13A0.55120.50620.32040.047*
C20.6541 (3)0.4586 (3)0.46543 (7)0.0429 (6)
C12A0.8603 (3)0.5797 (3)0.26611 (7)0.0442 (6)
C140.6068 (3)0.5912 (3)0.38862 (7)0.0368 (5)
C100.9389 (4)0.6353 (3)0.17097 (7)0.0495 (7)
C10.6662 (3)0.4597 (3)0.41563 (7)0.0419 (6)
H10.71470.37160.39970.050*
C8A0.7339 (3)0.6636 (3)0.23836 (7)0.0401 (6)
C80.5622 (3)0.7255 (3)0.25968 (7)0.0512 (7)
H8A0.53360.82830.24550.061*
H8B0.46370.65270.25230.061*
C130.8241 (4)0.5543 (3)0.31951 (7)0.0513 (7)
H13B0.85210.44450.32770.062*
H13C0.90460.62260.33800.062*
C50.4542 (4)0.8583 (3)0.38460 (7)0.0532 (7)
H5A0.54170.94480.38430.064*
H5B0.34410.89640.40000.064*
C90.7799 (4)0.6871 (3)0.19070 (7)0.0440 (6)
C111.0623 (4)0.5526 (3)0.19728 (8)0.0658 (8)
H111.16990.51550.18370.079*
C121.0202 (4)0.5261 (3)0.24547 (8)0.0629 (8)
H121.10230.47020.26460.076*
C60.4132 (4)0.8065 (3)0.33314 (7)0.0555 (7)
H6A0.31890.72570.33310.067*
H6B0.37110.89700.31430.067*
C160.5070 (4)0.7089 (4)0.56528 (8)0.0742 (9)
H16A0.57440.80440.55850.089*
H16B0.51320.68590.59920.089*
H16C0.38260.72370.55600.089*
C150.7866 (4)0.7644 (4)0.11353 (8)0.0714 (9)
H15A0.72150.71170.08760.086*
H15B0.81300.87290.10350.086*
C170.7351 (5)0.1838 (3)0.47281 (9)0.0715 (9)
H17A0.62750.15390.45540.086*
H17B0.75930.10610.49750.086*
H17C0.83600.18870.45090.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0976 (15)0.0967 (15)0.0305 (8)0.0313 (15)0.0120 (10)0.0171 (9)
O20.0907 (15)0.0877 (14)0.0338 (9)0.0042 (14)0.0191 (10)0.0055 (9)
O30.0601 (11)0.0657 (11)0.0255 (7)0.0056 (11)0.0009 (8)0.0046 (7)
O40.0963 (14)0.0519 (10)0.0317 (8)0.0176 (11)0.0022 (9)0.0084 (8)
N70.0505 (11)0.0437 (11)0.0301 (8)0.0124 (11)0.0059 (9)0.0077 (8)
C4A0.0376 (12)0.0392 (13)0.0355 (11)0.0012 (12)0.0030 (10)0.0003 (10)
C30.0392 (12)0.0492 (14)0.0282 (10)0.0020 (13)0.0016 (10)0.0020 (10)
C40.0457 (13)0.0429 (14)0.0380 (11)0.0032 (13)0.0085 (10)0.0062 (11)
C13A0.0536 (15)0.0361 (12)0.0276 (10)0.0022 (12)0.0010 (10)0.0021 (10)
C20.0522 (14)0.0448 (14)0.0315 (11)0.0017 (13)0.0008 (11)0.0037 (11)
C12A0.0572 (15)0.0427 (13)0.0327 (11)0.0045 (14)0.0061 (11)0.0025 (10)
C140.0433 (13)0.0388 (12)0.0281 (10)0.0031 (12)0.0017 (10)0.0007 (10)
C100.0688 (18)0.0488 (15)0.0310 (11)0.0047 (15)0.0092 (13)0.0059 (11)
C10.0574 (15)0.0375 (13)0.0308 (11)0.0031 (13)0.0008 (11)0.0006 (10)
C8A0.0538 (15)0.0370 (12)0.0294 (10)0.0001 (12)0.0018 (10)0.0012 (10)
C80.0612 (16)0.0587 (15)0.0339 (11)0.0140 (16)0.0051 (11)0.0114 (11)
C130.0651 (17)0.0584 (16)0.0305 (11)0.0213 (15)0.0056 (12)0.0049 (11)
C50.0663 (18)0.0490 (14)0.0441 (12)0.0198 (14)0.0176 (13)0.0076 (12)
C90.0635 (17)0.0367 (12)0.0318 (11)0.0000 (13)0.0011 (12)0.0021 (10)
C110.0670 (19)0.084 (2)0.0468 (14)0.0159 (19)0.0164 (15)0.0091 (15)
C120.0710 (19)0.0752 (19)0.0426 (13)0.0264 (17)0.0047 (13)0.0030 (14)
C60.0600 (17)0.0635 (17)0.0430 (12)0.0257 (16)0.0092 (13)0.0123 (13)
C160.080 (2)0.108 (2)0.0343 (12)0.032 (2)0.0061 (13)0.0134 (16)
C150.102 (2)0.0782 (19)0.0343 (12)0.003 (2)0.0094 (15)0.0095 (14)
C170.112 (3)0.0535 (16)0.0487 (14)0.0256 (19)0.0029 (17)0.0108 (14)
Geometric parameters (Å, º) top
O1—C91.380 (3)C10—C111.355 (3)
O1—C151.425 (3)C10—C91.363 (3)
O2—C101.378 (2)C1—H10.93
O2—C151.417 (3)C8A—C91.376 (3)
O3—C31.368 (2)C8A—C81.489 (3)
O3—C161.419 (3)C8—H8A0.97
O4—C21.369 (2)C8—H8B0.97
O4—C171.413 (3)C13—H13B0.97
N7—C61.452 (3)C13—H13C0.97
N7—C13A1.463 (3)C5—C61.519 (3)
N7—C81.467 (2)C5—H5A0.97
C4A—C141.382 (3)C5—H5B0.97
C4A—C41.411 (3)C11—C121.387 (3)
C4A—C51.501 (3)C11—H110.93
C3—C41.363 (3)C12—H120.93
C3—C21.398 (3)C6—H6A0.97
C4—H40.93C6—H6B0.97
C13A—C131.516 (3)C16—H16A0.96
C13A—C141.524 (2)C16—H16B0.96
C13A—H13A0.98C16—H16C0.96
C2—C11.381 (2)C15—H15A0.97
C12A—C121.384 (4)C15—H15B0.97
C12A—C8A1.397 (3)C17—H17A0.96
C12A—C131.517 (3)C17—H17B0.96
C14—C11.402 (3)C17—H17C0.96
C9—O1—C15105.4 (2)C13A—C13—C12A113.2 (2)
C10—O2—C15105.52 (19)C13A—C13—H13B108.9
C3—O3—C16117.46 (19)C12A—C13—H13B108.9
C2—O4—C17118.12 (17)C13A—C13—H13C108.9
C6—N7—C13A112.00 (18)C12A—C13—H13C108.9
C6—N7—C8111.18 (18)H13B—C13—H13C107.7
C13A—N7—C8109.98 (18)C4A—C5—C6109.40 (19)
C14—C4A—C4119.1 (2)C4A—C5—H5A109.8
C14—C4A—C5120.73 (18)C6—C5—H5A109.8
C4—C4A—C5120.2 (2)C4A—C5—H5B109.8
C4—C3—O3125.9 (2)C6—C5—H5B109.8
C4—C3—C2119.28 (17)H5A—C5—H5B108.2
O3—C3—C2114.9 (2)C10—C9—C8A123.3 (2)
C3—C4—C4A121.7 (2)C10—C9—O1109.92 (19)
C3—C4—H4119.2C8A—C9—O1126.7 (2)
C4A—C4—H4119.2C10—C11—C12116.6 (3)
N7—C13A—C13107.8 (2)C10—C11—H11121.7
N7—C13A—C14111.78 (18)C12—C11—H11121.7
C13—C13A—C14111.49 (19)C12A—C12—C11122.4 (3)
N7—C13A—H13A108.6C12A—C12—H12118.8
C13—C13A—H13A108.6C11—C12—H12118.8
C14—C13A—H13A108.6N7—C6—C5108.2 (2)
O4—C2—C1124.7 (2)N7—C6—H6A110.1
O4—C2—C3115.67 (17)C5—C6—H6A110.1
C1—C2—C3119.7 (2)N7—C6—H6B110.1
C12—C12A—C8A120.3 (2)C5—C6—H6B110.1
C12—C12A—C13120.4 (2)H6A—C6—H6B108.4
C8A—C12A—C13119.3 (2)O3—C16—H16A109.5
C4A—C14—C1119.07 (18)O3—C16—H16B109.5
C4A—C14—C13A121.7 (2)H16A—C16—H16B109.5
C1—C14—C13A119.3 (2)O3—C16—H16C109.5
C11—C10—C9121.6 (2)H16A—C16—H16C109.5
C11—C10—O2128.1 (2)H16B—C16—H16C109.5
C9—C10—O2110.3 (2)O2—C15—O1108.81 (19)
C2—C1—C14121.1 (2)O2—C15—H15A109.9
C2—C1—H1119.4O1—C15—H15A109.9
C14—C1—H1119.4O2—C15—H15B109.9
C9—C8A—C12A115.8 (2)O1—C15—H15B109.9
C9—C8A—C8122.6 (2)H15A—C15—H15B108.3
C12A—C8A—C8121.58 (18)O4—C17—H17A109.5
N7—C8—C8A110.88 (18)O4—C17—H17B109.5
N7—C8—H8A109.5H17A—C17—H17B109.5
C8A—C8—H8A109.5O4—C17—H17C109.5
N7—C8—H8B109.5H17A—C17—H17C109.5
C8A—C8—H8B109.5H17B—C17—H17C109.5
H8A—C8—H8B108.1
C16—O3—C3—C40.6 (4)C12—C12A—C8A—C8178.9 (2)
C16—O3—C3—C2178.5 (2)C13—C12A—C8A—C81.5 (3)
O3—C3—C4—C4A178.4 (2)C6—N7—C8—C8A178.6 (2)
C2—C3—C4—C4A2.5 (4)C13A—N7—C8—C8A56.7 (3)
C14—C4A—C4—C30.1 (4)C9—C8A—C8—N7156.9 (2)
C5—C4A—C4—C3178.8 (2)C12A—C8A—C8—N722.0 (3)
C6—N7—C13A—C13165.75 (18)N7—C13A—C13—C12A47.0 (3)
C8—N7—C13A—C1370.1 (2)C14—C13A—C13—C12A170.0 (2)
C6—N7—C13A—C1442.9 (3)C12—C12A—C13—C13A168.4 (2)
C8—N7—C13A—C14167.07 (19)C8A—C12A—C13—C13A14.2 (3)
C17—O4—C2—C117.5 (4)C14—C4A—C5—C621.4 (3)
C17—O4—C2—C3163.0 (2)C4—C4A—C5—C6157.6 (2)
C4—C3—C2—O4177.6 (2)C11—C10—C9—C8A1.5 (4)
O3—C3—C2—O41.5 (3)O2—C10—C9—C8A177.4 (2)
C4—C3—C2—C12.8 (4)C11—C10—C9—O1179.2 (2)
O3—C3—C2—C1178.0 (2)O2—C10—C9—O11.8 (3)
C4—C4A—C14—C12.5 (3)C12A—C8A—C9—C100.9 (3)
C5—C4A—C14—C1176.5 (2)C8—C8A—C9—C10178.0 (2)
C4—C4A—C14—C13A177.4 (2)C12A—C8A—C9—O1179.9 (2)
C5—C4A—C14—C13A3.7 (3)C8—C8A—C9—O11.1 (4)
N7—C13A—C14—C4A6.1 (3)C15—O1—C9—C101.7 (3)
C13—C13A—C14—C4A126.8 (2)C15—O1—C9—C8A177.5 (2)
N7—C13A—C14—C1173.8 (2)C9—C10—C11—C121.2 (4)
C13—C13A—C14—C153.1 (3)O2—C10—C11—C12177.6 (3)
C15—O2—C10—C11180.0 (3)C8A—C12A—C12—C110.2 (4)
C15—O2—C10—C91.1 (3)C13—C12A—C12—C11177.2 (3)
O4—C2—C1—C14180.0 (2)C10—C11—C12—C12A0.4 (4)
C3—C2—C1—C140.5 (4)C13A—N7—C6—C570.0 (2)
C4A—C14—C1—C22.2 (4)C8—N7—C6—C5166.5 (2)
C13A—C14—C1—C2177.7 (2)C4A—C5—C6—N756.5 (3)
C12—C12A—C8A—C90.1 (3)C10—O2—C15—O10.1 (3)
C13—C12A—C8A—C9177.5 (2)C9—O1—C15—O21.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···O3i0.972.583.504 (3)160
C17—H17C···O2ii0.962.593.527 (4)166
C16—H16C···Cg1i0.962.653.489 (3)146
C6—H6B···Cg2iii0.972.813.697 (3)153
Table headnote: Cg1 and Cg2 denote the centroids of —the C1–C4/C4A/C14 and C9–C12/C12A/C8A rings, respectively.
Symmetry codes: (i) x1/2, y+3/2, z+1; (ii) x+2, y1/2, z+1/2; (iii) x+1, y+1/2, z+1/2.
 

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