Redetermination of ternifoline-C at 150 K

The relative stereochemistry of ternifoline-C (7,20-epoxy-ent-kaur-16-ene-1,6,7,15-tetrol 1-acetate), C₂₂H₃₂O₆, previously reported by Wu [Fudan Xuebao Zir. Kex. (1988), 27, 61-65], has been redetermined at 150 K. The molecular geometry and crystal packing agree well with the previous study.

Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR97 (Altomare et al.,1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PLATON (Spek, 1998) and SHELXL97.

ent-Kaur-16-ene-1,6,7,15-tetrol-7,20-epoxy-1-acetate

Crystal data

C22H32O6	F(000) = 424
Mr = 392.48	Dx = 1.313 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 10.9870 (16) Å	Cell parameters from 3394 reflections
b = 6.0330 (8) Å	θ = 1.9–27.5°
c = 15.429 (3) Å	µ = 0.09 mm^−1
β = 103.989 (6)°	T = 150 K
V = 992.4 (3) Å^3	Needle, colourless
Z = 2	0.15 × 0.05 × 0.02 mm

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	3394 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2168 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.074
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
φ and ω scans to fill Ewald sphere	h = −14→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −5→7
Tmin = 0.987, Tmax = 0.998	l = −18→18
7295 measured reflections

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)] = 0.059	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0484P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
3394 reflections	Δρmax = 0.21 e Å^−3
268 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1054 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 1.7 (16)

Special details

Experimental. Please note cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

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	0.1111 (2)	1.0909 (4)	0.25661 (15)	0.0333 (6)
O2	−0.0723 (2)	0.7328 (5)	0.08201 (18)	0.0338 (7)
H2	−0.097 (5)	0.831 (10)	0.052 (3)	0.074 (19)*
O3	0.0583 (3)	1.1301 (5)	0.10578 (17)	0.0356 (6)
H3	0.112 (3)	1.249 (8)	0.113 (2)	0.043 (12)*
O4	0.1339 (3)	0.5287 (4)	0.06129 (16)	0.0335 (6)
H4	0.057 (4)	0.572 (8)	0.057 (3)	0.057 (14)*
O5	0.2501 (2)	0.6552 (5)	0.45729 (15)	0.0362 (7)
O6	0.3354 (2)	0.3276 (5)	0.50887 (17)	0.0461 (7)
C1	0.1542 (3)	0.5484 (7)	0.3864 (2)	0.0316 (9)
H1	0.1869	0.4031	0.3705	0.034 (2)*
C2	0.0430 (3)	0.5085 (7)	0.4252 (2)	0.0343 (9)
H2A	0.0210	0.6479	0.4516	0.034 (2)*
H2B	0.0653	0.3968	0.4734	0.034 (2)*
C3	−0.0700 (3)	0.4272 (7)	0.3542 (3)	0.0354 (9)
H3A	−0.1398	0.3953	0.3826	0.034 (2)*
H3B	−0.0479	0.2875	0.3281	0.034 (2)*
C4	−0.1131 (3)	0.5974 (7)	0.2800 (2)	0.0326 (9)
C5	0.0008 (3)	0.6505 (6)	0.2400 (2)	0.0283 (8)
H5	0.0149	0.5126	0.2078	0.034 (2)*
C6	−0.0260 (3)	0.8312 (6)	0.1686 (2)	0.0291 (8)
H6	−0.0929	0.9300	0.1809	0.034 (2)*
C7	0.0907 (3)	0.9705 (6)	0.1736 (2)	0.0298 (9)
C8	0.2091 (3)	0.8381 (7)	0.1716 (2)	0.0306 (9)
C9	0.2298 (3)	0.6652 (6)	0.2495 (2)	0.0284 (8)
H9	0.2130	0.5154	0.2214	0.034 (2)*
C10	0.1306 (3)	0.7037 (6)	0.3048 (2)	0.0293 (9)
C11	0.3674 (3)	0.6655 (7)	0.3041 (2)	0.0346 (9)
H11A	0.3820	0.7991	0.3425	0.034 (2)*
H11B	0.3816	0.5341	0.3437	0.034 (2)*
C12	0.4632 (3)	0.6625 (7)	0.2461 (3)	0.0415 (10)
H12A	0.4737	0.5085	0.2269	0.034 (2)*
H12B	0.5454	0.7145	0.2820	0.034 (2)*
C13	0.4206 (3)	0.8128 (8)	0.1623 (2)	0.0405 (10)
H13	0.4937	0.8854	0.1458	0.034 (2)*
C14	0.3257 (3)	0.9849 (7)	0.1797 (3)	0.0365 (9)
H14A	0.3534	1.0512	0.2399	0.034 (2)*
H14B	0.3108	1.1041	0.1342	0.034 (2)*
C15	0.2059 (4)	0.7275 (7)	0.0806 (3)	0.0364 (10)
H15	0.1739	0.8373	0.0319	0.034 (2)*
C16	0.3427 (4)	0.6803 (7)	0.0852 (3)	0.0399 (10)
C17	0.3851 (4)	0.5429 (8)	0.0328 (3)	0.0569 (13)
H17A	0.3278	0.4635	−0.0127	0.034 (2)*
H17B	0.4728	0.5234	0.0404	0.034 (2)*
C18	−0.2165 (3)	0.4924 (7)	0.2065 (3)	0.0388 (10)
H18A	−0.2450	0.5997	0.1581	0.063 (4)*
H18B	−0.2871	0.4498	0.2313	0.063 (4)*
H18C	−0.1832	0.3607	0.1830	0.063 (4)*
C19	−0.1700 (3)	0.8005 (7)	0.3168 (2)	0.0391 (10)
H19A	−0.1970	0.9097	0.2690	0.063 (4)*
H19B	−0.1067	0.8670	0.3657	0.063 (4)*
H19C	−0.2423	0.7535	0.3390	0.063 (4)*
C20	0.1412 (3)	0.9457 (6)	0.3338 (2)	0.0326 (9)
H20A	0.0830	0.9751	0.3725	0.034 (2)*
H20B	0.2276	0.9762	0.3689	0.034 (2)*
C21	0.3326 (3)	0.5256 (8)	0.5142 (2)	0.0379 (10)
C22	0.4189 (4)	0.6643 (8)	0.5830 (3)	0.0502 (12)
H22A	0.5033	0.6608	0.5724	0.063 (4)*
H22B	0.4215	0.6054	0.6426	0.063 (4)*
H22C	0.3883	0.8174	0.5790	0.063 (4)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0458 (15)	0.0243 (15)	0.0276 (14)	0.0004 (12)	0.0045 (11)	−0.0015 (11)
O2	0.0390 (15)	0.0308 (16)	0.0278 (15)	−0.0034 (13)	0.0007 (12)	−0.0009 (13)
O3	0.0453 (15)	0.0249 (15)	0.0327 (14)	−0.0025 (13)	0.0017 (11)	0.0061 (13)
O4	0.0350 (15)	0.0281 (15)	0.0361 (15)	−0.0027 (13)	0.0062 (12)	−0.0013 (12)
O5	0.0396 (14)	0.0337 (16)	0.0306 (14)	0.0012 (13)	−0.0005 (11)	0.0024 (13)
O6	0.0523 (17)	0.0378 (18)	0.0436 (17)	0.0069 (14)	0.0027 (13)	0.0076 (15)
C1	0.0364 (19)	0.027 (2)	0.028 (2)	−0.0019 (18)	0.0023 (16)	0.0049 (17)
C2	0.040 (2)	0.033 (2)	0.030 (2)	0.0018 (18)	0.0088 (16)	0.0040 (18)
C3	0.038 (2)	0.029 (2)	0.041 (2)	−0.0001 (19)	0.0133 (17)	0.0011 (19)
C4	0.0308 (19)	0.032 (2)	0.035 (2)	0.0002 (17)	0.0082 (16)	−0.0002 (18)
C5	0.0316 (19)	0.0244 (19)	0.0261 (18)	0.0009 (17)	0.0018 (15)	−0.0002 (17)
C6	0.0297 (17)	0.026 (2)	0.029 (2)	−0.0022 (17)	0.0019 (14)	0.0007 (17)
C7	0.040 (2)	0.021 (2)	0.026 (2)	0.0013 (17)	0.0015 (16)	−0.0003 (16)
C8	0.0330 (19)	0.026 (2)	0.030 (2)	−0.0022 (17)	0.0028 (15)	0.0015 (18)
C9	0.0287 (18)	0.0246 (19)	0.031 (2)	0.0006 (17)	0.0052 (15)	0.0028 (17)
C10	0.033 (2)	0.030 (2)	0.0231 (18)	0.0020 (17)	0.0029 (15)	0.0035 (16)
C11	0.0298 (18)	0.036 (2)	0.035 (2)	0.0025 (18)	0.0017 (16)	−0.0008 (19)
C12	0.0326 (19)	0.044 (3)	0.044 (2)	0.001 (2)	0.0033 (17)	0.000 (2)
C13	0.037 (2)	0.045 (3)	0.041 (2)	−0.009 (2)	0.0120 (17)	−0.001 (2)
C14	0.042 (2)	0.034 (2)	0.034 (2)	−0.0068 (19)	0.0102 (17)	0.0000 (19)
C15	0.044 (2)	0.030 (2)	0.033 (2)	−0.0042 (18)	0.0046 (17)	−0.0034 (18)
C16	0.039 (2)	0.041 (3)	0.042 (2)	−0.005 (2)	0.0135 (18)	−0.001 (2)
C17	0.044 (2)	0.069 (3)	0.058 (3)	0.006 (3)	0.013 (2)	−0.022 (3)
C18	0.0314 (19)	0.038 (3)	0.046 (2)	−0.0070 (19)	0.0071 (17)	−0.001 (2)
C19	0.038 (2)	0.039 (2)	0.041 (2)	0.0056 (19)	0.0092 (17)	0.002 (2)
C20	0.0372 (19)	0.028 (2)	0.030 (2)	0.0039 (18)	0.0033 (16)	0.0059 (18)
C21	0.036 (2)	0.044 (3)	0.035 (2)	0.000 (2)	0.0090 (17)	0.009 (2)
C22	0.046 (2)	0.055 (3)	0.041 (2)	−0.007 (2)	−0.0072 (19)	0.004 (2)

Geometric parameters (Å, º)

O1—C7	1.442 (4)	C9—C11	1.543 (4)
O1—C20	1.451 (4)	C9—C10	1.556 (5)
O2—C6	1.438 (4)	C9—H9	1.0000
O2—H2	0.76 (5)	C10—C20	1.523 (5)
O3—C7	1.403 (4)	C11—C12	1.537 (5)
O3—H3	0.92 (4)	C11—H11A	0.9900
O4—C15	1.428 (4)	C11—H11B	0.9900
O4—H4	0.87 (4)	C12—C13	1.557 (6)
O5—C21	1.349 (5)	C12—H12A	0.9900
O5—C1	1.471 (4)	C12—H12B	0.9900
O6—C21	1.198 (5)	C13—C16	1.515 (6)
C1—C2	1.504 (5)	C13—C14	1.540 (6)
C1—C10	1.540 (5)	C13—H13	1.0000
C1—H1	1.0000	C14—H14A	0.9900
C2—C3	1.524 (5)	C14—H14B	0.9900
C2—H2A	0.9900	C15—C16	1.515 (6)
C2—H2B	0.9900	C15—H15	1.0000
C3—C4	1.526 (5)	C16—C17	1.319 (6)
C3—H3A	0.9900	C17—H17A	0.9500
C3—H3B	0.9900	C17—H17B	0.9500
C4—C18	1.535 (5)	C18—H18A	0.9800
C4—C19	1.544 (5)	C18—H18B	0.9800
C4—C5	1.557 (5)	C18—H18C	0.9800
C5—C6	1.527 (5)	C19—H19A	0.9800
C5—C10	1.564 (5)	C19—H19B	0.9800
C5—H5	1.0000	C19—H19C	0.9800
C6—C7	1.519 (5)	C20—H20A	0.9900
C6—H6	1.0000	C20—H20B	0.9900
C7—C8	1.533 (5)	C21—C22	1.496 (6)
C8—C14	1.538 (5)	C22—H22A	0.9800
C8—C15	1.547 (5)	C22—H22B	0.9800
C8—C9	1.566 (5)	C22—H22C	0.9800
C7—O1—C20	112.4 (3)	C9—C10—C5	105.7 (3)
C6—O2—H2	104 (4)	C12—C11—C9	113.6 (3)
C7—O3—H3	114 (2)	C12—C11—H11A	108.8
C15—O4—H4	104 (3)	C9—C11—H11A	108.8
C21—O5—C1	118.5 (3)	C12—C11—H11B	108.8
O5—C1—C2	106.2 (3)	C9—C11—H11B	108.8
O5—C1—C10	106.9 (3)	H11A—C11—H11B	107.7
C2—C1—C10	115.4 (3)	C11—C12—C13	111.5 (3)
O5—C1—H1	109.4	C11—C12—H12A	109.3
C2—C1—H1	109.4	C13—C12—H12A	109.3
C10—C1—H1	109.4	C11—C12—H12B	109.3
C1—C2—C3	111.4 (3)	C13—C12—H12B	109.3
C1—C2—H2A	109.3	H12A—C12—H12B	108.0
C3—C2—H2A	109.3	C16—C13—C14	102.4 (3)
C1—C2—H2B	109.3	C16—C13—C12	110.1 (4)
C3—C2—H2B	109.3	C14—C13—C12	109.1 (3)
H2A—C2—H2B	108.0	C16—C13—H13	111.6
C2—C3—C4	111.9 (3)	C14—C13—H13	111.6
C2—C3—H3A	109.2	C12—C13—H13	111.6
C4—C3—H3A	109.2	C8—C14—C13	100.6 (3)
C2—C3—H3B	109.2	C8—C14—H14A	111.7
C4—C3—H3B	109.2	C13—C14—H14A	111.7
H3A—C3—H3B	107.9	C8—C14—H14B	111.7
C3—C4—C18	108.5 (3)	C13—C14—H14B	111.7
C3—C4—C19	109.8 (3)	H14A—C14—H14B	109.4
C18—C4—C19	107.9 (3)	O4—C15—C16	110.2 (3)
C3—C4—C5	107.6 (3)	O4—C15—C8	116.2 (3)
C18—C4—C5	108.3 (3)	C16—C15—C8	103.5 (3)
C19—C4—C5	114.7 (3)	O4—C15—H15	108.9
C6—C5—C4	113.6 (3)	C16—C15—H15	108.9
C6—C5—C10	107.6 (3)	C8—C15—H15	108.9
C4—C5—C10	119.0 (3)	C17—C16—C15	125.7 (4)
C6—C5—H5	105.2	C17—C16—C13	126.6 (4)
C4—C5—H5	105.2	C15—C16—C13	107.7 (3)
C10—C5—H5	105.2	C16—C17—H17A	120.0
O2—C6—C7	112.3 (3)	C16—C17—H17B	120.0
O2—C6—C5	109.8 (3)	H17A—C17—H17B	120.0
C7—C6—C5	110.2 (3)	C4—C18—H18A	109.5
O2—C6—H6	108.1	C4—C18—H18B	109.5
C7—C6—H6	108.1	H18A—C18—H18B	109.5
C5—C6—H6	108.1	C4—C18—H18C	109.5
O3—C7—O1	105.9 (3)	H18A—C18—H18C	109.5
O3—C7—C6	106.5 (3)	H18B—C18—H18C	109.5
O1—C7—C6	105.8 (3)	C4—C19—H19A	109.5
O3—C7—C8	114.0 (3)	C4—C19—H19B	109.5
O1—C7—C8	109.2 (3)	H19A—C19—H19B	109.5
C6—C7—C8	114.9 (3)	C4—C19—H19C	109.5
C7—C8—C14	113.1 (3)	H19A—C19—H19C	109.5
C7—C8—C15	114.2 (3)	H19B—C19—H19C	109.5
C14—C8—C15	99.1 (3)	O1—C20—C10	110.6 (3)
C7—C8—C9	107.4 (3)	O1—C20—H20A	109.5
C14—C8—C9	111.0 (3)	C10—C20—H20A	109.5
C15—C8—C9	112.1 (3)	O1—C20—H20B	109.5
C11—C9—C10	115.1 (3)	C10—C20—H20B	109.5
C11—C9—C8	111.1 (3)	H20A—C20—H20B	108.1
C10—C9—C8	109.3 (3)	O6—C21—O5	123.9 (4)
C11—C9—H9	107.0	O6—C21—C22	125.7 (4)
C10—C9—H9	107.0	O5—C21—C22	110.4 (4)
C8—C9—H9	107.0	C21—C22—H22A	109.5
C20—C10—C1	110.9 (3)	C21—C22—H22B	109.5
C20—C10—C9	106.9 (3)	H22A—C22—H22B	109.5
C1—C10—C9	110.8 (3)	C21—C22—H22C	109.5
C20—C10—C5	112.2 (3)	H22A—C22—H22C	109.5
C1—C10—C5	110.2 (3)	H22B—C22—H22C	109.5
C21—O5—C1—C2	89.9 (4)	C2—C1—C10—C9	−158.6 (3)
C21—O5—C1—C10	−146.4 (3)	O5—C1—C10—C5	−159.9 (3)
O5—C1—C2—C3	172.1 (3)	C2—C1—C10—C5	−42.0 (4)
C10—C1—C2—C3	53.9 (5)	C11—C9—C10—C20	71.1 (4)
C1—C2—C3—C4	−61.8 (4)	C8—C9—C10—C20	−54.7 (4)
C2—C3—C4—C18	173.4 (3)	C11—C9—C10—C1	−49.8 (4)
C2—C3—C4—C19	−68.9 (4)	C8—C9—C10—C1	−175.6 (3)
C2—C3—C4—C5	56.5 (4)	C11—C9—C10—C5	−169.2 (3)
C3—C4—C5—C6	−176.1 (3)	C8—C9—C10—C5	65.0 (4)
C18—C4—C5—C6	66.8 (4)	C6—C5—C10—C20	47.3 (4)
C19—C4—C5—C6	−53.7 (4)	C4—C5—C10—C20	−83.6 (4)
C3—C4—C5—C10	−48.0 (4)	C6—C5—C10—C1	171.4 (3)
C18—C4—C5—C10	−165.1 (3)	C4—C5—C10—C1	40.6 (5)
C19—C4—C5—C10	74.5 (4)	C6—C5—C10—C9	−68.8 (4)
C4—C5—C6—O2	−90.7 (4)	C4—C5—C10—C9	160.3 (3)
C10—C5—C6—O2	135.5 (3)	C10—C9—C11—C12	−171.2 (3)
C4—C5—C6—C7	145.1 (3)	C8—C9—C11—C12	−46.3 (4)
C10—C5—C6—C7	11.3 (4)	C9—C11—C12—C13	39.5 (5)
C20—O1—C7—O3	177.8 (3)	C11—C12—C13—C16	−90.0 (4)
C20—O1—C7—C6	65.1 (3)	C11—C12—C13—C14	21.7 (4)
C20—O1—C7—C8	−59.0 (4)	C7—C8—C14—C13	−172.3 (3)
O2—C6—C7—O3	56.8 (4)	C15—C8—C14—C13	−51.1 (3)
C5—C6—C7—O3	179.5 (3)	C9—C8—C14—C13	66.9 (4)
O2—C6—C7—O1	169.1 (3)	C16—C13—C14—C8	42.4 (4)
C5—C6—C7—O1	−68.1 (4)	C12—C13—C14—C8	−74.3 (3)
O2—C6—C7—C8	−70.4 (4)	C7—C8—C15—O4	−78.1 (4)
C5—C6—C7—C8	52.4 (4)	C14—C8—C15—O4	161.4 (3)
O3—C7—C8—C14	58.6 (4)	C9—C8—C15—O4	44.3 (4)
O1—C7—C8—C14	−59.6 (4)	C7—C8—C15—C16	161.0 (3)
C6—C7—C8—C14	−178.2 (3)	C14—C8—C15—C16	40.5 (4)
O3—C7—C8—C15	−53.7 (4)	C9—C8—C15—C16	−76.7 (4)
O1—C7—C8—C15	−171.9 (3)	O4—C15—C16—C17	38.5 (6)
C6—C7—C8—C15	69.5 (4)	C8—C15—C16—C17	163.4 (5)
O3—C7—C8—C9	−178.7 (3)	O4—C15—C16—C13	−139.7 (3)
O1—C7—C8—C9	63.1 (4)	C8—C15—C16—C13	−14.8 (4)
C6—C7—C8—C9	−55.4 (4)	C14—C13—C16—C17	164.8 (5)
C7—C8—C9—C11	−132.9 (3)	C12—C13—C16—C17	−79.2 (5)
C14—C8—C9—C11	−8.8 (4)	C14—C13—C16—C15	−17.0 (4)
C15—C8—C9—C11	101.0 (4)	C12—C13—C16—C15	99.0 (4)
C7—C8—C9—C10	−4.7 (4)	C7—O1—C20—C10	−5.3 (4)
C14—C8—C9—C10	119.4 (3)	C1—C10—C20—O1	−176.5 (3)
C15—C8—C9—C10	−130.9 (3)	C9—C10—C20—O1	62.6 (3)
O5—C1—C10—C20	−35.0 (4)	C5—C10—C20—O1	−52.7 (4)
C2—C1—C10—C20	82.9 (4)	C1—O5—C21—O6	2.5 (6)
O5—C1—C10—C9	83.5 (3)	C1—O5—C21—C22	−177.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4^i	0.76 (6)	2.07 (5)	2.795 (4)	158 (5)
O3—H3···O4^ii	0.92 (4)	1.91 (5)	2.687 (4)	142 (3)
O4—H4···O2	0.87 (5)	1.84 (5)	2.665 (5)	158 (4)

Symmetry codes: (i) −x, y+1/2, −z; (ii) x, y+1, z.