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The title compound, C22H30N2O, was prepared from (-)-17-oxosparteine. The lactam N atom is essentially planar, lying 0.0150 (12) Å out of the plane of its three bonded C atoms, and the C=O distance is 1.2315 (13) Å. The conformation of the sparteine ring system is nearly identical to that of 17-oxosparteine.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023808/hg6002sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023808/hg6002Isup2.hkl
Contains datablock I

CCDC reference: 227028

Key indicators

  • Single-crystal X-ray study
  • T = 100 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.089
  • Data-to-parameter ratio = 17.6

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.99
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 33.70 From the CIF: _reflns_number_total 4004 Count of symmetry unique reflns 4056 Completeness (_total/calc) 98.72% 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 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

(+)-6-benzyl-17-oxosparteine top
Crystal data top
C22H30N2OF(000) = 736
Mr = 338.48Dx = 1.233 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3909 reflections
a = 10.236 (2) Åθ = 2.5–34.3°
b = 10.947 (2) ŵ = 0.08 mm1
c = 16.278 (2) ÅT = 100 K
V = 1824.0 (5) Å3Prism, colorless
Z = 40.40 × 0.40 × 0.37 mm
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
3769 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 33.7°, θmin = 2.7°
ω scans with κ offsetsh = 1515
22786 measured reflectionsk = 1717
4004 independent reflectionsl = 2424
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0457P)2 + 0.2882P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4004 reflectionsΔρmax = 0.29 e Å3
227 parametersΔρmin = 0.20 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (2)
Special details top

Experimental. The completeness of the data to θmax = 30° is 0.998.

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
O10.74242 (9)0.49036 (8)0.44079 (5)0.02074 (16)
N10.62550 (10)0.33718 (9)0.49936 (6)0.01840 (17)
N20.49430 (8)0.51583 (8)0.62845 (5)0.01491 (16)
C20.37991 (10)0.59091 (11)0.64800 (7)0.01779 (18)
H2A0.39490.63430.70050.021*
H2B0.30260.53760.65490.021*
C30.35341 (11)0.68355 (11)0.58049 (7)0.0211 (2)
H3A0.27910.73620.59660.025*
H3B0.32930.64030.52930.025*
C40.47379 (11)0.76248 (10)0.56506 (7)0.0203 (2)
H4A0.49100.81450.61360.024*
H4B0.45830.81650.51730.024*
C50.59191 (11)0.68044 (10)0.54836 (6)0.01615 (18)
H5A0.67050.73240.54240.019*
H5B0.57820.63720.49560.019*
C60.61704 (9)0.58556 (9)0.61606 (6)0.01389 (16)
C70.72458 (9)0.49389 (10)0.58792 (6)0.01497 (17)
H70.80940.53910.58540.018*
C80.74102 (11)0.38808 (10)0.64840 (7)0.01892 (19)
H8A0.80960.33130.62900.023*
H8B0.76640.41930.70320.023*
C90.60958 (11)0.32286 (10)0.65307 (7)0.01895 (19)
H90.61710.25470.69370.023*
C100.50666 (11)0.41230 (10)0.68404 (6)0.01848 (19)
H10A0.42140.37010.68860.022*
H10B0.53140.44180.73940.022*
C110.57332 (11)0.26788 (10)0.56941 (7)0.01833 (19)
H110.47590.26800.56490.022*
C120.61998 (13)0.13444 (10)0.56258 (8)0.0242 (2)
H12A0.71580.13150.57070.029*
H12B0.57880.08560.60670.029*
C130.58647 (13)0.07773 (11)0.47943 (9)0.0260 (2)
H13A0.62570.00470.47570.031*
H13B0.49050.06910.47450.031*
C140.63753 (13)0.15688 (12)0.40938 (8)0.0256 (2)
H14A0.73420.15530.40930.031*
H14B0.60670.12360.35630.031*
C150.59018 (13)0.28802 (11)0.41889 (7)0.0232 (2)
H15A0.62950.33930.37530.028*
H15B0.49410.29060.41230.028*
C170.69769 (10)0.44134 (9)0.50281 (6)0.01569 (17)
C180.66307 (10)0.65137 (10)0.69704 (6)0.01668 (18)
H18A0.59320.70800.71490.020*
H18B0.67350.58900.74060.020*
C190.78917 (11)0.72257 (10)0.69026 (6)0.01696 (18)
C200.91009 (11)0.66757 (11)0.70535 (7)0.0200 (2)
H200.91310.58420.72130.024*
C211.02617 (11)0.73267 (13)0.69741 (7)0.0236 (2)
H211.10720.69350.70820.028*
C221.02430 (12)0.85501 (13)0.67375 (7)0.0242 (2)
H221.10350.89910.66700.029*
C230.90468 (13)0.91144 (12)0.66014 (7)0.0247 (2)
H230.90210.99510.64480.030*
C240.78853 (12)0.84648 (11)0.66883 (7)0.0208 (2)
H240.70760.88690.66010.025*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0245 (4)0.0217 (4)0.0161 (3)0.0010 (3)0.0040 (3)0.0002 (3)
N10.0248 (4)0.0150 (4)0.0154 (4)0.0012 (3)0.0003 (3)0.0015 (3)
N20.0136 (3)0.0153 (3)0.0159 (4)0.0005 (3)0.0013 (3)0.0005 (3)
C20.0150 (4)0.0196 (4)0.0187 (4)0.0004 (4)0.0021 (3)0.0026 (4)
C30.0161 (4)0.0225 (5)0.0247 (5)0.0040 (4)0.0011 (4)0.0011 (4)
C40.0217 (5)0.0161 (4)0.0231 (5)0.0029 (4)0.0001 (4)0.0014 (4)
C50.0175 (4)0.0160 (4)0.0149 (4)0.0000 (4)0.0008 (3)0.0021 (3)
C60.0137 (4)0.0151 (4)0.0129 (4)0.0001 (3)0.0006 (3)0.0007 (3)
C70.0148 (4)0.0164 (4)0.0137 (4)0.0008 (4)0.0004 (3)0.0009 (3)
C80.0194 (4)0.0203 (5)0.0170 (4)0.0034 (4)0.0026 (4)0.0019 (4)
C90.0228 (5)0.0171 (4)0.0169 (4)0.0011 (4)0.0002 (4)0.0043 (4)
C100.0215 (4)0.0186 (4)0.0153 (4)0.0014 (4)0.0033 (3)0.0034 (4)
C110.0199 (4)0.0145 (4)0.0205 (4)0.0000 (4)0.0012 (4)0.0019 (4)
C120.0272 (5)0.0143 (4)0.0310 (6)0.0019 (4)0.0002 (5)0.0013 (4)
C130.0247 (5)0.0152 (4)0.0381 (6)0.0002 (4)0.0009 (5)0.0051 (4)
C140.0257 (5)0.0222 (5)0.0288 (6)0.0014 (5)0.0010 (4)0.0108 (4)
C150.0308 (6)0.0199 (5)0.0190 (5)0.0017 (5)0.0032 (4)0.0045 (4)
C170.0153 (4)0.0156 (4)0.0161 (4)0.0020 (3)0.0006 (3)0.0013 (3)
C180.0165 (4)0.0191 (4)0.0144 (4)0.0017 (4)0.0005 (3)0.0020 (3)
C190.0179 (4)0.0196 (4)0.0133 (4)0.0025 (4)0.0006 (3)0.0027 (4)
C200.0186 (4)0.0234 (5)0.0180 (4)0.0011 (4)0.0019 (4)0.0020 (4)
C210.0172 (4)0.0338 (6)0.0197 (5)0.0020 (4)0.0009 (4)0.0036 (5)
C220.0220 (5)0.0342 (6)0.0165 (4)0.0100 (5)0.0003 (4)0.0014 (5)
C230.0272 (5)0.0241 (5)0.0230 (5)0.0079 (5)0.0031 (4)0.0019 (4)
C240.0204 (4)0.0205 (5)0.0214 (5)0.0025 (4)0.0020 (4)0.0007 (4)
Geometric parameters (Å, º) top
O1—C171.2315 (13)C10—H10A0.99
N1—C171.3599 (14)C10—H10B0.99
N1—C151.4615 (14)C11—C121.5409 (16)
N1—C111.4700 (14)C11—H111.00
N2—C101.4557 (14)C12—C131.5281 (18)
N2—C21.4655 (14)C12—H12A0.99
N2—C61.4839 (13)C12—H12B0.99
C2—C31.5197 (16)C13—C141.5245 (19)
C2—H2A0.99C13—H13A0.99
C2—H2B0.99C13—H13B0.99
C3—C41.5258 (17)C14—C151.5230 (18)
C3—H3A0.99C14—H14A0.99
C3—H3B0.99C14—H14B0.99
C4—C51.5305 (16)C15—H15A0.99
C4—H4A0.99C15—H15B0.99
C4—H4B0.99C18—C191.5119 (15)
C5—C61.5360 (14)C18—H18A0.99
C5—H5A0.99C18—H18B0.99
C5—H5B0.99C19—C201.3982 (16)
C6—C71.5584 (14)C19—C241.4006 (17)
C6—C181.5744 (14)C20—C211.3916 (17)
C7—C171.5251 (14)C20—H200.95
C7—C81.5295 (15)C21—C221.394 (2)
C7—H71.00C21—H210.95
C8—C91.5251 (16)C22—C231.3892 (18)
C8—H8A0.99C22—H220.95
C8—H8B0.99C23—C241.3926 (17)
C9—C101.5240 (16)C23—H230.95
C9—C111.5345 (16)C24—H240.95
C9—H91.00
C17—N1—C15118.69 (9)H10A—C10—H10B108.1
C17—N1—C11126.74 (9)N1—C11—C9113.46 (9)
C15—N1—C11114.54 (9)N1—C11—C12108.70 (9)
C10—N2—C2111.79 (8)C9—C11—C12111.15 (9)
C10—N2—C6114.29 (8)N1—C11—H11107.8
C2—N2—C6114.67 (9)C9—C11—H11107.8
N2—C2—C3111.09 (9)C12—C11—H11107.8
N2—C2—H2A109.4C13—C12—C11112.30 (10)
C3—C2—H2A109.4C13—C12—H12A109.1
N2—C2—H2B109.4C11—C12—H12A109.1
C3—C2—H2B109.4C13—C12—H12B109.1
H2A—C2—H2B108.0C11—C12—H12B109.1
C2—C3—C4110.66 (9)H12A—C12—H12B107.9
C2—C3—H3A109.5C14—C13—C12110.77 (10)
C4—C3—H3A109.5C14—C13—H13A109.5
C2—C3—H3B109.5C12—C13—H13A109.5
C4—C3—H3B109.5C14—C13—H13B109.5
H3A—C3—H3B108.1C12—C13—H13B109.5
C3—C4—C5109.56 (9)H13A—C13—H13B108.1
C3—C4—H4A109.8C15—C14—C13110.52 (10)
C5—C4—H4A109.8C15—C14—H14A109.5
C3—C4—H4B109.8C13—C14—H14A109.5
C5—C4—H4B109.8C15—C14—H14B109.5
H4A—C4—H4B108.2C13—C14—H14B109.5
C4—C5—C6113.69 (9)H14A—C14—H14B108.1
C4—C5—H5A108.8N1—C15—C14111.07 (10)
C6—C5—H5A108.8N1—C15—H15A109.4
C4—C5—H5B108.8C14—C15—H15A109.4
C6—C5—H5B108.8N1—C15—H15B109.4
H5A—C5—H5B107.7C14—C15—H15B109.4
N2—C6—C5107.67 (8)H15A—C15—H15B108.0
N2—C6—C7107.86 (8)O1—C17—N1122.24 (10)
C5—C6—C7110.05 (8)O1—C17—C7120.88 (9)
N2—C6—C18112.02 (8)N1—C17—C7116.86 (9)
C5—C6—C18109.96 (8)C19—C18—C6115.48 (8)
C7—C6—C18109.23 (8)C19—C18—H18A108.4
C17—C7—C8108.60 (9)C6—C18—H18A108.4
C17—C7—C6112.48 (8)C19—C18—H18B108.4
C8—C7—C6112.10 (8)C6—C18—H18B108.4
C17—C7—H7107.8H18A—C18—H18B107.5
C8—C7—H7107.8C20—C19—C24117.71 (10)
C6—C7—H7107.8C20—C19—C18121.39 (10)
C9—C8—C7106.83 (8)C24—C19—C18120.90 (10)
C9—C8—H8A110.4C21—C20—C19121.27 (11)
C7—C8—H8A110.4C21—C20—H20119.4
C9—C8—H8B110.4C19—C20—H20119.4
C7—C8—H8B110.4C20—C21—C22120.40 (12)
H8A—C8—H8B108.6C20—C21—H21119.8
C10—C9—C8109.00 (9)C22—C21—H21119.8
C10—C9—C11112.23 (9)C23—C22—C21118.92 (11)
C8—C9—C11110.65 (9)C23—C22—H22120.5
C10—C9—H9108.3C21—C22—H22120.5
C8—C9—H9108.3C22—C23—C24120.62 (11)
C11—C9—H9108.3C22—C23—H23119.7
N2—C10—C9110.78 (8)C24—C23—H23119.7
N2—C10—H10A109.5C23—C24—C19121.05 (11)
C9—C10—H10A109.5C23—C24—H24119.5
N2—C10—H10B109.5C19—C24—H24119.5
C9—C10—H10B109.5
C10—N2—C2—C3169.16 (9)C10—C9—C11—N191.72 (11)
C6—N2—C2—C358.68 (11)C8—C9—C11—N130.28 (12)
N2—C2—C3—C455.83 (12)C10—C9—C11—C12145.41 (10)
C2—C3—C4—C553.67 (12)C8—C9—C11—C1292.60 (11)
C3—C4—C5—C654.56 (12)N1—C11—C12—C1353.80 (13)
C10—N2—C6—C5173.04 (8)C9—C11—C12—C13179.37 (10)
C2—N2—C6—C556.01 (10)C11—C12—C13—C1453.61 (14)
C10—N2—C6—C754.30 (10)C12—C13—C14—C1553.09 (14)
C2—N2—C6—C7174.74 (8)C17—N1—C15—C14123.27 (11)
C10—N2—C6—C1865.94 (11)C11—N1—C15—C1458.69 (13)
C2—N2—C6—C1865.02 (11)C13—C14—C15—N154.92 (14)
C4—C5—C6—N253.98 (11)C15—N1—C17—O15.57 (16)
C4—C5—C6—C7171.30 (8)C11—N1—C17—O1176.65 (10)
C4—C5—C6—C1868.32 (11)C15—N1—C17—C7176.07 (10)
N2—C6—C7—C1767.21 (10)C11—N1—C17—C71.71 (15)
C5—C6—C7—C1749.99 (11)C8—C7—C17—O1143.40 (10)
C18—C6—C7—C17170.81 (8)C6—C7—C17—O191.93 (12)
N2—C6—C7—C855.52 (10)C8—C7—C17—N134.98 (12)
C5—C6—C7—C8172.72 (8)C6—C7—C17—N189.69 (11)
C18—C6—C7—C866.46 (11)N2—C6—C18—C19178.82 (9)
C17—C7—C8—C965.04 (10)C5—C6—C18—C1961.49 (11)
C6—C7—C8—C959.86 (11)C7—C6—C18—C1959.38 (11)
C7—C8—C9—C1060.62 (11)C6—C18—C19—C2089.33 (12)
C7—C8—C9—C1163.25 (11)C6—C18—C19—C2490.91 (12)
C2—N2—C10—C9169.18 (9)C24—C19—C20—C211.57 (15)
C6—N2—C10—C958.47 (11)C18—C19—C20—C21178.65 (11)
C8—C9—C10—N260.58 (11)C19—C20—C21—C220.22 (17)
C11—C9—C10—N262.36 (12)C20—C21—C22—C231.48 (17)
C17—N1—C11—C91.00 (15)C21—C22—C23—C240.90 (17)
C15—N1—C11—C9178.86 (10)C22—C23—C24—C190.94 (17)
C17—N1—C11—C12125.21 (12)C20—C19—C24—C232.15 (16)
C15—N1—C11—C1256.93 (13)C18—C19—C24—C23178.07 (10)
 

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