8-Oxocanadine

The title compound, C₂₀H₁₉NO₅, a protoberberine-type alkaloid, was isolated from the roots of the plant Sinomenium acutum. The piperidine ring adopts a screw-boat conformation and the pyridinone ring is in an envelope conformation.

Key indicators

• Single-crystal X-ray study
• T = 286 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.040
• wR factor = 0.076
• Data-to-parameter ratio = 6.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT048_ALERT_1_C MoietyFormula Not Given ........................          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.94
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

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           25.24
           From the CIF: _reflns_number_total               1651
           Count of symmetry unique reflns         1651
           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
   4 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
   0 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

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.

(I)

Crystal data

C20H19NO5	F(000) = 372
Mr = 353.36	Dx = 1.401 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 5.132 (2) Å	Cell parameters from 33 reflections
b = 7.203 (2) Å	θ = 3.9–15.5°
c = 22.767 (8) Å	µ = 0.10 mm^−1
β = 95.59 (3)°	T = 286 K
V = 837.5 (5) Å^3	Needle, yellow
Z = 2	0.56 × 0.24 × 0.20 mm

Data collection

Siemens P4 diffractometer	Rint = 0.016
Radiation source: normal-focus sealed tube	θmax = 25.2°, θmin = 1.8°
Graphite monochromator	h = 0→6
ω scans	k = 0→8
2412 measured reflections	l = −27→27
1651 independent reflections	3 standard reflections every 97 reflections
1165 reflections with I > 2σ(I)	intensity decay: 3.5%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.076	w = 1/[σ^2(Fo^2) + (0.0306P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
1651 reflections	Δρmax = 0.14 e Å^−3
238 parameters	Δρmin = −0.16 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0134 (19)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.8939 (5)	0.1808 (4)	0.11412 (10)	0.0671 (8)
O2	0.8235 (5)	0.3580 (4)	0.02937 (9)	0.0647 (8)
O3	0.0356 (5)	1.0173 (3)	0.26661 (10)	0.0609 (8)
O4	−0.0769 (5)	0.9773 (3)	0.38007 (10)	0.0484 (7)
O5	−0.2044 (5)	0.7366 (4)	0.45937 (9)	0.0668 (8)
N7	0.3033 (5)	0.8033 (3)	0.23256 (11)	0.0426 (8)
C1	0.6743 (6)	0.3960 (5)	0.17792 (14)	0.0447 (9)
H1	0.7042	0.3232	0.2116	0.054*
C2	0.7615 (7)	0.3428 (5)	0.12622 (14)	0.0467 (9)
C3	0.7162 (7)	0.4473 (6)	0.07549 (14)	0.0511 (10)
C4	0.5849 (8)	0.6090 (5)	0.07458 (15)	0.0540 (10)
H4	0.5561	0.6784	0.0401	0.065*
C4A	0.4926 (7)	0.6697 (5)	0.12751 (14)	0.0458 (9)
C5	0.3507 (8)	0.8535 (5)	0.12886 (13)	0.0563 (10)
H5A	0.4170	0.9381	0.1007	0.068*
H5B	0.1653	0.8349	0.1177	0.068*
C6	0.3897 (7)	0.9364 (5)	0.18976 (13)	0.0536 (10)
H6A	0.5731	0.9659	0.1996	0.064*
H6B	0.2895	1.0503	0.1910	0.064*
C8	0.1376 (7)	0.8630 (5)	0.27118 (14)	0.0440 (9)
C8A	0.0878 (6)	0.7324 (5)	0.32014 (13)	0.0375 (8)
C9	−0.0297 (7)	0.7909 (5)	0.36971 (15)	0.0416 (9)
C10	−0.0895 (8)	0.6643 (5)	0.41240 (15)	0.0488 (10)
C11	−0.0319 (7)	0.4787 (5)	0.40589 (15)	0.0562 (10)
H11	−0.0743	0.3935	0.4341	0.067*
C12	0.0893 (7)	0.4185 (5)	0.35715 (15)	0.0554 (10)
H12	0.1299	0.2935	0.3534	0.066*
C12A	0.1497 (6)	0.5429 (5)	0.31430 (14)	0.0421 (9)
C13	0.2703 (7)	0.4810 (5)	0.26095 (14)	0.0476 (9)
H13A	0.1325	0.4495	0.2304	0.057*
H13B	0.3721	0.3696	0.2704	0.057*
C13A	0.4449 (7)	0.6256 (4)	0.23752 (14)	0.0409 (9)
H13C	0.5992	0.6409	0.2660	0.049*
C14	0.5364 (7)	0.5658 (5)	0.17897 (14)	0.0398 (8)
C18	0.9758 (9)	0.2101 (6)	0.05727 (15)	0.0748 (13)
H18A	0.9511	0.0977	0.0339	0.090*
H18B	1.1602	0.2423	0.0605	0.090*
C19	−0.3406 (7)	1.0315 (5)	0.36281 (15)	0.0596 (10)
H19A	−0.3763	1.0194	0.3208	0.071*
H19B	−0.3653	1.1583	0.3740	0.071*
H19C	−0.4578	0.9533	0.3820	0.071*
C20	−0.3266 (8)	0.6116 (6)	0.49627 (16)	0.0703 (12)
H20A	−0.4562	0.5403	0.4729	0.084*
H20B	−0.4089	0.6804	0.5255	0.084*
H20C	−0.1974	0.5297	0.5154	0.084*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.099 (2)	0.0483 (16)	0.0579 (15)	0.0243 (16)	0.0276 (15)	0.0074 (13)
O2	0.096 (2)	0.0543 (16)	0.0453 (13)	0.0210 (18)	0.0168 (14)	0.0018 (14)
O3	0.086 (2)	0.0387 (16)	0.0610 (15)	0.0150 (16)	0.0254 (14)	0.0109 (14)
O4	0.0625 (17)	0.0340 (15)	0.0490 (14)	−0.0072 (14)	0.0073 (12)	−0.0054 (12)
O5	0.108 (2)	0.0506 (17)	0.0472 (13)	−0.0143 (17)	0.0333 (15)	−0.0050 (14)
N7	0.057 (2)	0.0300 (16)	0.0430 (16)	0.0035 (15)	0.0160 (15)	0.0039 (14)
C1	0.053 (2)	0.038 (2)	0.0436 (19)	0.0036 (19)	0.0078 (17)	0.0067 (16)
C2	0.060 (2)	0.034 (2)	0.047 (2)	0.004 (2)	0.0082 (18)	0.0038 (17)
C3	0.063 (3)	0.047 (2)	0.043 (2)	0.008 (2)	0.0065 (18)	−0.0047 (19)
C4	0.075 (3)	0.049 (2)	0.037 (2)	0.010 (2)	0.003 (2)	0.0087 (18)
C4A	0.054 (2)	0.037 (2)	0.046 (2)	0.0091 (19)	0.0079 (18)	0.0016 (18)
C5	0.081 (3)	0.047 (2)	0.0415 (19)	0.019 (2)	0.0093 (18)	0.0105 (19)
C6	0.078 (3)	0.035 (2)	0.049 (2)	0.000 (2)	0.0160 (19)	0.0071 (18)
C8	0.054 (2)	0.035 (2)	0.043 (2)	−0.004 (2)	0.0046 (18)	0.0017 (18)
C8A	0.043 (2)	0.0319 (18)	0.0381 (18)	−0.0025 (17)	0.0064 (17)	0.0006 (15)
C9	0.046 (2)	0.036 (2)	0.042 (2)	−0.0066 (18)	0.0000 (17)	−0.0018 (17)
C10	0.069 (3)	0.037 (2)	0.041 (2)	−0.004 (2)	0.009 (2)	−0.0024 (17)
C11	0.072 (3)	0.047 (2)	0.051 (2)	−0.004 (2)	0.014 (2)	0.015 (2)
C12	0.073 (3)	0.034 (2)	0.062 (2)	0.000 (2)	0.022 (2)	0.0057 (19)
C12A	0.045 (2)	0.034 (2)	0.047 (2)	−0.0024 (18)	0.0055 (17)	−0.0012 (17)
C13	0.055 (2)	0.033 (2)	0.056 (2)	−0.0018 (19)	0.0078 (18)	0.0021 (18)
C13A	0.049 (2)	0.033 (2)	0.0410 (19)	0.0003 (18)	0.0034 (16)	−0.0023 (17)
C14	0.046 (2)	0.036 (2)	0.0378 (18)	0.0025 (18)	0.0057 (16)	−0.0012 (16)
C18	0.104 (4)	0.063 (3)	0.061 (2)	0.032 (3)	0.028 (2)	0.006 (2)
C19	0.066 (3)	0.048 (2)	0.067 (2)	0.000 (2)	0.014 (2)	−0.012 (2)
C20	0.097 (3)	0.063 (3)	0.056 (2)	−0.006 (3)	0.030 (2)	0.005 (2)

Geometric parameters (Å, º)

O1—C2	1.392 (4)	C6—H6B	0.9700
O1—C18	1.415 (4)	C8—C8A	1.499 (5)
O2—C3	1.390 (4)	C8A—C9	1.395 (4)
O2—C18	1.433 (4)	C8A—C12A	1.411 (5)
O3—C8	1.229 (4)	C9—C10	1.389 (5)
O4—C9	1.389 (4)	C10—C11	1.380 (5)
O4—C19	1.426 (4)	C11—C12	1.393 (4)
O5—C10	1.373 (4)	C11—H11	0.9300
O5—C20	1.418 (4)	C12—C12A	1.382 (4)
N7—C8	1.352 (4)	C12—H12	0.9300
N7—C6	1.466 (4)	C12A—C13	1.484 (4)
N7—C13A	1.471 (4)	C13—C13A	1.505 (4)
C1—C2	1.355 (4)	C13—H13A	0.9700
C1—C14	1.415 (5)	C13—H13B	0.9700
C1—H1	0.9300	C13A—C14	1.518 (4)
C2—C3	1.379 (4)	C13A—H13C	0.9800
C3—C4	1.345 (5)	C18—H18A	0.9700
C4—C4A	1.407 (5)	C18—H18B	0.9700
C4—H4	0.9300	C19—H19A	0.9600
C4A—C14	1.390 (4)	C19—H19B	0.9600
C4A—C5	1.513 (5)	C19—H19C	0.9600
C5—C6	1.505 (4)	C20—H20A	0.9600
C5—H5A	0.9700	C20—H20B	0.9600
C5—H5B	0.9700	C20—H20C	0.9600
C6—H6A	0.9700
C2—O1—C18	104.5 (3)	O5—C10—C9	115.9 (3)
C3—O2—C18	104.4 (2)	C11—C10—C9	119.8 (3)
C9—O4—C19	113.2 (3)	C10—C11—C12	120.3 (3)
C10—O5—C20	118.0 (3)	C10—C11—H11	119.9
C8—N7—C6	118.3 (3)	C12—C11—H11	119.9
C8—N7—C13A	124.4 (3)	C12A—C12—C11	120.6 (3)
C6—N7—C13A	116.2 (3)	C12A—C12—H12	119.7
C2—C1—C14	117.9 (3)	C11—C12—H12	119.7
C2—C1—H1	121.1	C12—C12A—C8A	119.5 (3)
C14—C1—H1	121.1	C12—C12A—C13	121.5 (3)
C1—C2—C3	122.0 (3)	C8A—C12A—C13	118.9 (3)
C1—C2—O1	128.2 (3)	C12A—C13—C13A	113.1 (3)
C3—C2—O1	109.7 (3)	C12A—C13—H13A	109.0
C4—C3—C2	121.9 (3)	C13A—C13—H13A	109.0
C4—C3—O2	128.6 (3)	C12A—C13—H13B	109.0
C2—C3—O2	109.5 (3)	C13A—C13—H13B	109.0
C3—C4—C4A	117.8 (3)	H13A—C13—H13B	107.8
C3—C4—H4	121.1	N7—C13A—C13	108.8 (3)
C4A—C4—H4	121.1	N7—C13A—C14	111.9 (3)
C14—C4A—C4	121.0 (3)	C13—C13A—C14	111.1 (3)
C14—C4A—C5	119.5 (3)	N7—C13A—H13C	108.3
C4—C4A—C5	119.5 (3)	C13—C13A—H13C	108.3
C6—C5—C4A	110.2 (3)	C14—C13A—H13C	108.3
C6—C5—H5A	109.6	C4A—C14—C1	119.4 (3)
C4A—C5—H5A	109.6	C4A—C14—C13A	123.3 (3)
C6—C5—H5B	109.6	C1—C14—C13A	117.3 (3)
C4A—C5—H5B	109.6	O1—C18—O2	108.6 (3)
H5A—C5—H5B	108.1	O1—C18—H18A	110.0
N7—C6—C5	109.3 (3)	O2—C18—H18A	110.0
N7—C6—H6A	109.8	O1—C18—H18B	110.0
C5—C6—H6A	109.8	O2—C18—H18B	110.0
N7—C6—H6B	109.8	H18A—C18—H18B	108.4
C5—C6—H6B	109.8	O4—C19—H19A	109.5
H6A—C6—H6B	108.3	O4—C19—H19B	109.5
O3—C8—N7	121.5 (3)	H19A—C19—H19B	109.5
O3—C8—C8A	121.9 (3)	O4—C19—H19C	109.5
N7—C8—C8A	116.6 (3)	H19A—C19—H19C	109.5
C9—C8A—C12A	119.1 (3)	H19B—C19—H19C	109.5
C9—C8A—C8	122.0 (3)	O5—C20—H20A	109.5
C12A—C8A—C8	118.7 (3)	O5—C20—H20B	109.5
C10—C9—O4	117.5 (3)	H20A—C20—H20B	109.5
C10—C9—C8A	120.7 (3)	O5—C20—H20C	109.5
O4—C9—C8A	121.7 (3)	H20A—C20—H20C	109.5
O5—C10—C11	124.3 (3)	H20B—C20—H20C	109.5
C14—C1—C2—C3	−0.9 (5)	C20—O5—C10—C9	164.9 (3)
C14—C1—C2—O1	−178.0 (3)	O4—C9—C10—O5	3.6 (5)
C18—O1—C2—C1	−170.5 (4)	C8A—C9—C10—O5	179.9 (3)
C18—O1—C2—C3	12.1 (4)	O4—C9—C10—C11	−176.2 (4)
C1—C2—C3—C4	0.7 (6)	C8A—C9—C10—C11	0.1 (6)
O1—C2—C3—C4	178.3 (3)	O5—C10—C11—C12	−178.8 (3)
C1—C2—C3—O2	−179.0 (3)	C9—C10—C11—C12	1.0 (6)
O1—C2—C3—O2	−1.4 (4)	C10—C11—C12—C12A	−1.0 (6)
C18—O2—C3—C4	170.6 (4)	C11—C12—C12A—C8A	0.0 (5)
C18—O2—C3—C2	−9.8 (4)	C11—C12—C12A—C13	−177.8 (3)
C2—C3—C4—C4A	−0.2 (6)	C9—C8A—C12A—C12	1.0 (5)
O2—C3—C4—C4A	179.4 (3)	C8—C8A—C12A—C12	−175.8 (3)
C3—C4—C4A—C14	0.1 (6)	C9—C8A—C12A—C13	178.9 (3)
C3—C4—C4A—C5	178.3 (3)	C8—C8A—C12A—C13	2.1 (5)
C14—C4A—C5—C6	26.8 (5)	C12—C12A—C13—C13A	−149.6 (3)
C4—C4A—C5—C6	−151.4 (3)	C8A—C12A—C13—C13A	32.6 (5)
C8—N7—C6—C5	−129.9 (3)	C8—N7—C13A—C13	36.7 (4)
C13A—N7—C6—C5	61.8 (4)	C6—N7—C13A—C13	−155.8 (3)
C4A—C5—C6—N7	−56.0 (4)	C8—N7—C13A—C14	159.9 (3)
C6—N7—C8—O3	8.7 (5)	C6—N7—C13A—C14	−32.6 (4)
C13A—N7—C8—O3	175.9 (3)	C12A—C13—C13A—N7	−49.3 (4)
C6—N7—C8—C8A	−170.5 (3)	C12A—C13—C13A—C14	−172.9 (3)
C13A—N7—C8—C8A	−3.3 (4)	C4—C4A—C14—C1	−0.4 (5)
O3—C8—C8A—C9	−13.8 (5)	C5—C4A—C14—C1	−178.6 (3)
N7—C8—C8A—C9	165.4 (3)	C4—C4A—C14—C13A	179.1 (3)
O3—C8—C8A—C12A	162.9 (3)	C5—C4A—C14—C13A	0.9 (5)
N7—C8—C8A—C12A	−17.9 (5)	C2—C1—C14—C4A	0.8 (5)
C19—O4—C9—C10	−84.5 (4)	C2—C1—C14—C13A	−178.7 (3)
C19—O4—C9—C8A	99.2 (4)	N7—C13A—C14—C4A	0.8 (4)
C12A—C8A—C9—C10	−1.1 (5)	C13—C13A—C14—C4A	122.6 (4)
C8—C8A—C9—C10	175.6 (3)	N7—C13A—C14—C1	−179.7 (3)
C12A—C8A—C9—O4	175.0 (3)	C13—C13A—C14—C1	−57.8 (4)
C8—C8A—C9—O4	−8.3 (5)	C2—O1—C18—O2	−18.3 (4)
C20—O5—C10—C11	−15.3 (6)	C3—O2—C18—O1	17.5 (4)