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The title compound, C22H25N3O3, also known as fumitremorgine C, was isolated from the ethyl ­acetate extract of Penicillium sp. To a first approximation, the mol­ecule is flat with the exception of the –C(H)=CMe2 side arm, which is perpendicular to the remaining atoms. Mol­ecules associate into one-dimensional chains via N—H...O and C—H...O inter­actions involving both carbonyl O atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007513/sj2013sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007513/sj2013Isup2.hkl
Contains datablock I

CCDC reference: 605181

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.044
  • wR factor = 0.136
  • Data-to-parameter ratio = 7.8

checkCIF/PLATON results

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Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.80 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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 26.00 From the CIF: _reflns_number_total 2004 Count of symmetry unique reflns 2013 Completeness (_total/calc) 99.55% 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 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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: 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: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

1,2,3,5a,6,11,12,14a-Octahydro-9-methoxy-12-(2-methylprop-1-enyl)-5H,14H- pyrrolo[1'',2'':4',5']pyrazino[1',2':1,6]pyrido[3,4-b]indole-5,14-dione top
Crystal data top
C22H25N3O3Dx = 1.257 Mg m3
Mr = 379.45Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P43Cell parameters from 25 reflections
Hall symbol: P 4cwθ = 10.0–13.0°
a = 8.7795 (12) ŵ = 0.09 mm1
c = 26.020 (5) ÅT = 293 K
V = 2005.6 (5) Å3Block, colourless
Z = 40.40 × 0.30 × 0.20 mm
F(000) = 808
Data collection top
Siemens SMART CCD area-detector
diffractometer
1408 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.071
Graphite monochromatorθmax = 26.0°, θmin = 2.3°
φ and ω scansh = 010
2264 measured reflectionsk = 010
2004 independent reflectionsl = 031
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)] = 0.044H-atom parameters constrained
wR(F2) = 0.136 w = 1/[σ2(Fo2) + (0.0569P)2 + 0.2013P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max < 0.001
2004 reflectionsΔρmax = 0.14 e Å3
257 parametersΔρmin = 0.18 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0095 (18)
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
O10.2650 (4)0.0338 (4)0.10095 (15)0.0788 (11)
O20.2452 (4)0.8695 (4)0.19196 (11)0.0692 (10)
O30.2923 (6)0.8985 (4)0.00825 (14)0.0911 (14)
N10.2770 (4)1.0150 (4)0.12177 (13)0.0501 (9)
N20.1910 (4)0.7758 (4)0.06060 (13)0.0449 (8)
N30.0156 (4)0.4016 (4)0.02792 (14)0.0491 (9)
H30.02230.38350.00450.059*
C10.2719 (8)0.1191 (7)0.0545 (2)0.0851 (18)
H1A0.33150.06470.02960.128*
H1B0.31800.21630.06110.128*
H1C0.17070.13400.04140.128*
C20.1928 (5)0.1052 (6)0.1002 (2)0.0579 (12)
C30.1811 (6)0.1751 (7)0.1488 (2)0.0705 (14)
H3A0.22190.12650.17740.085*
C40.1106 (6)0.3134 (6)0.15472 (19)0.0615 (13)
H40.10590.35920.18690.074*
C50.0458 (5)0.3850 (5)0.11189 (17)0.0497 (11)
C60.0602 (5)0.3131 (5)0.06333 (16)0.0453 (10)
C70.1351 (5)0.1747 (5)0.05681 (18)0.0517 (11)
H70.14580.13080.02450.062*
C80.0429 (5)0.5195 (5)0.10396 (15)0.0459 (10)
C90.1079 (6)0.6344 (5)0.14030 (15)0.0527 (11)
H9A0.20660.60000.15240.063*
H9B0.04130.64520.16980.063*
C100.1251 (5)0.7883 (5)0.11328 (16)0.0446 (9)
H100.02340.83340.11010.053*
C110.2213 (5)0.8949 (5)0.14583 (17)0.0480 (10)
C120.3764 (7)1.1285 (6)0.1457 (2)0.0651 (13)
H12A0.47321.08390.15550.078*
H12B0.32881.17290.17580.078*
C130.3974 (7)1.2477 (6)0.1031 (2)0.0688 (14)
H13A0.49871.29170.10440.083*
H13B0.32271.32860.10630.083*
C140.3736 (7)1.1569 (5)0.0531 (2)0.0669 (14)
H14A0.34211.22330.02530.080*
H14B0.46611.10420.04320.080*
C150.2499 (6)1.0460 (5)0.06664 (17)0.0525 (11)
H150.15121.09710.06300.063*
C160.2466 (6)0.9016 (5)0.03620 (18)0.0571 (12)
C170.1844 (5)0.6359 (5)0.02845 (15)0.0453 (10)
H170.14560.66210.00570.054*
C180.3425 (5)0.5726 (5)0.02344 (18)0.0508 (11)
H180.39150.54760.05400.061*
C190.4206 (6)0.5480 (5)0.0193 (2)0.0648 (14)
C200.3622 (8)0.5836 (7)0.0728 (2)0.090 (2)
H20A0.36120.49210.09300.135*
H20B0.42770.65730.08870.135*
H20C0.26080.62380.07050.135*
C210.5768 (7)0.4818 (8)0.0175 (3)0.101 (2)
H21A0.60830.47090.01760.151*
H21B0.64630.54810.03520.151*
H21C0.57660.38380.03390.151*
C220.0789 (5)0.5247 (5)0.05326 (16)0.0444 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.088 (2)0.080 (2)0.068 (3)0.028 (2)0.000 (2)0.0036 (19)
O20.096 (3)0.083 (2)0.0285 (19)0.031 (2)0.0115 (16)0.0018 (16)
O30.182 (4)0.056 (2)0.035 (2)0.001 (2)0.025 (2)0.0071 (16)
N10.064 (2)0.051 (2)0.0347 (19)0.0016 (18)0.0065 (17)0.0035 (16)
N20.064 (2)0.0449 (19)0.0256 (17)0.0057 (16)0.0026 (15)0.0008 (14)
N30.061 (2)0.060 (2)0.0263 (17)0.0010 (18)0.0013 (16)0.0117 (15)
C10.103 (4)0.080 (4)0.073 (4)0.016 (3)0.017 (4)0.017 (3)
C20.052 (3)0.067 (3)0.055 (3)0.008 (2)0.005 (2)0.006 (2)
C30.073 (3)0.095 (4)0.044 (3)0.029 (3)0.009 (2)0.002 (3)
C40.066 (3)0.077 (3)0.041 (3)0.017 (3)0.010 (2)0.011 (2)
C50.045 (2)0.068 (3)0.036 (2)0.003 (2)0.0051 (18)0.009 (2)
C60.044 (2)0.059 (3)0.033 (2)0.004 (2)0.0014 (17)0.0078 (18)
C70.050 (2)0.065 (3)0.040 (2)0.001 (2)0.000 (2)0.011 (2)
C80.046 (2)0.065 (3)0.027 (2)0.003 (2)0.0062 (17)0.0106 (18)
C90.061 (3)0.072 (3)0.026 (2)0.013 (2)0.0068 (19)0.007 (2)
C100.045 (2)0.059 (3)0.031 (2)0.0082 (18)0.0019 (17)0.0121 (18)
C110.051 (2)0.058 (3)0.035 (3)0.000 (2)0.0006 (19)0.008 (2)
C120.083 (3)0.060 (3)0.052 (3)0.014 (3)0.007 (3)0.000 (2)
C130.089 (4)0.057 (3)0.061 (3)0.005 (2)0.005 (3)0.000 (2)
C140.099 (4)0.052 (3)0.050 (3)0.003 (3)0.003 (3)0.008 (2)
C150.076 (3)0.042 (2)0.039 (3)0.013 (2)0.006 (2)0.0047 (18)
C160.087 (3)0.051 (3)0.033 (3)0.012 (2)0.000 (2)0.0015 (19)
C170.063 (3)0.049 (2)0.0234 (19)0.007 (2)0.0041 (18)0.0031 (17)
C180.063 (3)0.046 (2)0.044 (3)0.002 (2)0.010 (2)0.0007 (19)
C190.073 (3)0.052 (3)0.070 (3)0.001 (2)0.032 (3)0.001 (2)
C200.129 (5)0.091 (4)0.050 (4)0.012 (4)0.043 (3)0.012 (3)
C210.084 (4)0.093 (4)0.125 (6)0.008 (4)0.053 (4)0.001 (4)
C220.050 (2)0.053 (2)0.030 (2)0.0064 (19)0.0035 (18)0.0082 (18)
Geometric parameters (Å, º) top
O1—C11.423 (7)C9—H9A0.9700
O1—C21.375 (6)C9—H9B0.9700
O2—C111.239 (5)C10—C111.519 (6)
O3—C161.225 (6)C10—H100.9800
N1—C111.321 (6)C12—C131.534 (7)
N1—C121.463 (6)C12—H12A0.9700
N1—C151.479 (6)C12—H12B0.9700
N2—C101.492 (5)C13—C141.540 (7)
N2—C161.364 (6)C13—H13A0.9700
N2—C171.487 (5)C13—H13B0.9700
N3—C61.377 (5)C14—C151.500 (7)
N3—C221.382 (5)C14—H14A0.9700
N3—H30.8600C14—H14B0.9700
C1—H1A0.9600C15—C161.495 (7)
C1—H1B0.9600C15—H150.9800
C1—H1C0.9600C17—C221.493 (6)
C2—C71.379 (7)C17—C181.501 (6)
C2—C31.410 (7)C17—H170.9800
C3—C41.372 (7)C18—C191.325 (7)
C3—H3A0.9300C18—H180.9300
C4—C51.400 (6)C19—C211.491 (7)
C4—H40.9300C19—C201.514 (9)
C5—C61.418 (6)C20—H20A0.9600
C5—C81.429 (6)C20—H20B0.9600
C6—C71.392 (6)C20—H20C0.9600
C7—H70.9300C21—H21A0.9600
C8—C221.357 (6)C21—H21B0.9600
C8—C91.496 (6)C21—H21C0.9600
C9—C101.531 (6)
C1—O1—C2118.3 (4)N1—C12—H12A111.1
C11—N1—C12124.3 (4)C13—C12—H12A111.1
C11—N1—C15123.1 (4)N1—C12—H12B111.1
C12—N1—C15112.5 (4)C13—C12—H12B111.1
C10—N2—C16120.4 (3)H12A—C12—H12B109.1
C10—N2—C17124.3 (3)C12—C13—C14103.9 (4)
C16—N2—C17114.9 (3)C12—C13—H13A111.0
C6—N3—C22108.4 (3)C14—C13—H13A111.0
C6—N3—H3125.8C12—C13—H13B111.0
C22—N3—H3125.8C14—C13—H13B111.0
O1—C1—H1A109.5H13A—C13—H13B109.0
O1—C1—H1B109.5C15—C14—C13103.7 (4)
H1A—C1—H1B109.5C15—C14—H14A111.0
O1—C1—H1C109.5C13—C14—H14A111.0
H1A—C1—H1C109.5C15—C14—H14B111.0
H1B—C1—H1C109.5C13—C14—H14B111.0
O1—C2—C7125.0 (4)H14A—C14—H14B109.0
O1—C2—C3114.0 (4)N1—C15—C14103.3 (4)
C7—C2—C3121.0 (4)N1—C15—C16111.2 (3)
C4—C3—C2121.3 (5)C14—C15—C16116.1 (4)
C4—C3—H3A119.4N1—C15—H15108.7
C2—C3—H3A119.4C14—C15—H15108.7
C3—C4—C5119.4 (4)C16—C15—H15108.7
C3—C4—H4120.3O3—C16—N2122.6 (4)
C5—C4—H4120.3O3—C16—C15120.9 (5)
C4—C5—C6118.2 (4)N2—C16—C15116.5 (4)
C4—C5—C8135.0 (4)N2—C17—C22108.7 (3)
C6—C5—C8106.7 (4)N2—C17—C18108.6 (3)
N3—C6—C7129.8 (4)C22—C17—C18111.7 (3)
N3—C6—C5107.6 (4)N2—C17—H17109.3
C7—C6—C5122.6 (4)C22—C17—H17109.3
C2—C7—C6117.4 (4)C18—C17—H17109.3
C2—C7—H7121.3C17—C18—C19127.7 (5)
C6—C7—H7121.3C19—C18—H18116.1
C22—C8—C5107.2 (4)C17—C18—H18116.1
C22—C8—C9120.2 (4)C18—C19—C21120.9 (6)
C5—C8—C9132.4 (4)C18—C19—C20124.3 (5)
C8—C9—C10110.0 (4)C20—C19—C21114.9 (5)
C8—C9—H9A109.7C19—C20—H20A109.5
C10—C9—H9A109.7C19—C20—H20B109.5
C8—C9—H9B109.7H20A—C20—H20B109.5
C10—C9—H9B109.7C19—C20—H20C109.5
H9A—C9—H9B108.2H20A—C20—H20C109.5
N2—C10—C11110.0 (3)H20B—C20—H20C109.5
N2—C10—C9113.3 (3)C19—C21—H21A109.5
C11—C10—C9110.0 (4)C19—C21—H21B109.5
N2—C10—H10107.8H21A—C21—H21B109.5
C11—C10—H10107.8C19—C21—H21C109.5
C9—C10—H10107.8H21A—C21—H21C109.5
O2—C11—N1122.7 (4)H21B—C21—H21C109.5
O2—C11—C10121.6 (4)C8—C22—N3110.1 (4)
N1—C11—C10115.7 (4)C8—C22—C17125.9 (4)
N1—C12—C13103.3 (4)N3—C22—C17123.7 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3···O2i0.862.082.812 (5)143
C9—H9b···O3ii0.972.323.281 (6)171
Symmetry codes: (i) y+1, x, z1/4; (ii) y1, x+1, z+1/4.
 

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