21α-Fluoro-7-nor-12,13,15,16-tetra­hydro­vouacapane-17β,21α-lactone

As part of our studies on synthetic derivatives of 6α,7β-di­hydroxy­vouacapan-17β-oic acid, isolated from the seeds of Pterodon polygalaeflorus Benth, the structure of the title compound, C₂₀H₂₉FO₃, was determined. The crystal packing is stabilized by C—H...O and C—H...F intermolecular interactions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.043
• wR factor = 0.107
• Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C
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           26.29
           From the CIF: _reflns_number_total               2093
           Count of symmetry unique reflns         2096
           Completeness (_total/calc)             99.86%
           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
   1 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

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).

(II)

Crystal data

C20H29FO3	F(000) = 728
Mr = 336.43	Dx = 1.269 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 6.0284 (4) Å	θ = 10.3–18.3°
b = 10.850 (2) Å	µ = 0.09 mm^−1
c = 26.921 (3) Å	T = 293 K
V = 1760.8 (4) Å^3	Prism, colourless
Z = 4	0.02 × 0.01 × 0.01 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	θmax = 26.3°, θmin = 2.4°
non–profiled ω/2θ scans	h = −7→0
2095 measured reflections	k = −13→0
2093 independent reflections	l = 0→33
1125 reflections with I > 2σ(I)	3 standard reflections every 120 min
Rint = 0.046	intensity decay: 2%

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.044P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.107	(Δ/σ)max = 0.004
S = 1.00	Δρmax = 0.17 e Å^−3
2093 reflections	Δρmin = −0.21 e Å^−3
220 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F	0.4431 (4)	0.0249 (2)	0.17975 (8)	0.0567 (7)
O1	0.3507 (5)	0.4461 (3)	0.11689 (10)	0.0600 (8)
O2	0.1207 (6)	0.2461 (3)	0.27601 (10)	0.0806 (11)
O3	0.1926 (5)	0.0687 (2)	0.24009 (8)	0.0525 (8)
C1	0.0958 (7)	0.0882 (3)	0.01635 (11)	0.0447 (11)
H1A	0.0203	0.1473	−0.0048	0.054*
H1B	0.2529	0.1077	0.0161	0.054*
C2	0.0610 (8)	−0.0418 (4)	−0.00427 (13)	0.0539 (12)
H2A	−0.0967	−0.0571	−0.008	0.065*
H2B	0.1286	−0.0474	−0.0369	0.065*
C3	0.1606 (8)	−0.1393 (3)	0.02936 (13)	0.0525 (12)
H3A	0.3207	−0.1304	0.0287	0.063*
H3B	0.1258	−0.2196	0.0156	0.063*
C4	0.0846 (7)	−0.1375 (3)	0.08392 (13)	0.0397 (10)
C5	0.1143 (6)	−0.0039 (3)	0.10140 (11)	0.0320 (9)
H5	0.2739	0.0108	0.098	0.038*
C6	0.0629 (6)	0.0354 (3)	0.15562 (12)	0.0366 (9)
H6	−0.0815	0.0009	0.1649	0.044*
C8	0.0389 (6)	0.1763 (3)	0.15234 (11)	0.0337 (9)
H8	−0.1162	0.1978	0.159	0.04*
C9	0.0928 (7)	0.2116 (3)	0.09863 (11)	0.0343 (9)
H9	0.2548	0.2116	0.0956	0.041*
C10	0.0070 (6)	0.0991 (3)	0.06947 (11)	0.0338 (9)
C11	0.0158 (7)	0.3436 (3)	0.09017 (13)	0.0461 (11)
H11A	−0.1446	0.3477	0.0926	0.055*
H11B	0.0586	0.3704	0.0571	0.055*
C12	0.1204 (8)	0.4286 (4)	0.12910 (14)	0.0484 (11)
H12	0.0457	0.5088	0.1277	0.058*
C13	0.1280 (8)	0.3862 (4)	0.18337 (12)	0.0477 (11)
H13	−0.014	0.4031	0.1998	0.057*
C14	0.1850 (7)	0.2497 (3)	0.18726 (12)	0.0366 (9)
H14	0.3391	0.2392	0.1764	0.044*
C15	0.4668 (8)	0.4815 (4)	0.16016 (16)	0.0634 (12)
H15A	0.5192	0.5656	0.157	0.076*
H15B	0.5939	0.4281	0.1652	0.076*
C16	0.3080 (8)	0.4709 (4)	0.20380 (15)	0.0629 (13)
H16A	0.248	0.5507	0.2129	0.075*
H16B	0.3803	0.4346	0.2325	0.075*
C17	0.1641 (8)	0.1953 (4)	0.23823 (15)	0.0517 (11)
C18	0.2364 (8)	−0.2231 (4)	0.11365 (16)	0.0547 (12)
H18A	0.177	−0.234	0.1464	0.082*
H18B	0.3817	−0.1874	0.1159	0.082*
H18C	0.2456	−0.3016	0.0973	0.082*
C19	−0.1523 (8)	−0.1876 (4)	0.08895 (15)	0.0558 (12)
H19A	−0.2478	−0.1456	0.066	0.084*
H19B	−0.2043	−0.1743	0.1222	0.084*
H19C	−0.1529	−0.2743	0.0818	0.084*
C20	−0.2486 (6)	0.1014 (4)	0.06859 (14)	0.0502 (11)
H20A	−0.3045	0.0765	0.1004	0.075*
H20B	−0.3015	0.0457	0.0435	0.075*
H20C	−0.2989	0.1833	0.0613	0.075*
C21	0.2282 (7)	0.0012 (4)	0.19552 (13)	0.0470 (11)
H21	0.214	−0.087	0.2027	0.056*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.0483 (15)	0.0724 (16)	0.0494 (13)	0.0063 (14)	−0.0093 (12)	0.0025 (12)
O1	0.064 (2)	0.0598 (19)	0.0565 (17)	−0.0167 (17)	0.0080 (17)	−0.0020 (14)
O2	0.123 (3)	0.082 (2)	0.0377 (17)	−0.004 (2)	0.0167 (19)	−0.0153 (16)
O3	0.071 (2)	0.0596 (18)	0.0273 (13)	−0.0036 (17)	0.0002 (14)	0.0029 (13)
C1	0.051 (3)	0.051 (3)	0.0324 (19)	−0.003 (2)	0.000 (2)	0.0060 (18)
C2	0.066 (3)	0.060 (3)	0.035 (2)	−0.003 (3)	0.003 (2)	−0.005 (2)
C3	0.067 (3)	0.050 (3)	0.040 (2)	−0.005 (2)	0.004 (2)	−0.0136 (19)
C4	0.040 (3)	0.041 (2)	0.0380 (19)	−0.004 (2)	−0.0008 (19)	−0.0044 (17)
C5	0.031 (2)	0.038 (2)	0.0270 (16)	−0.0019 (19)	0.0002 (17)	0.0012 (15)
C6	0.034 (2)	0.043 (2)	0.0321 (19)	0.000 (2)	−0.0019 (19)	0.0007 (17)
C8	0.031 (2)	0.040 (2)	0.0308 (19)	0.0043 (19)	0.0005 (18)	−0.0018 (17)
C9	0.034 (2)	0.039 (2)	0.0303 (19)	−0.001 (2)	0.0020 (18)	0.0023 (16)
C10	0.033 (2)	0.040 (2)	0.0283 (18)	−0.0013 (19)	0.0012 (17)	0.0043 (18)
C11	0.058 (3)	0.038 (2)	0.041 (2)	0.006 (2)	−0.003 (2)	0.0025 (17)
C12	0.055 (3)	0.035 (2)	0.056 (2)	0.003 (2)	0.002 (2)	−0.0015 (19)
C13	0.053 (3)	0.049 (2)	0.041 (2)	0.000 (3)	0.006 (2)	−0.007 (2)
C14	0.036 (2)	0.046 (2)	0.0283 (18)	0.000 (2)	0.0008 (18)	−0.0010 (17)
C15	0.057 (3)	0.064 (3)	0.069 (3)	−0.012 (3)	−0.006 (3)	−0.003 (3)
C16	0.074 (3)	0.052 (3)	0.063 (3)	−0.006 (3)	−0.005 (3)	−0.014 (2)
C17	0.058 (3)	0.060 (3)	0.038 (2)	−0.005 (3)	−0.001 (2)	−0.005 (2)
C18	0.062 (3)	0.042 (2)	0.061 (3)	0.008 (2)	0.005 (2)	0.000 (2)
C19	0.054 (3)	0.055 (3)	0.058 (3)	−0.016 (2)	0.000 (2)	−0.005 (2)
C20	0.038 (2)	0.065 (3)	0.048 (2)	0.001 (2)	−0.0044 (19)	0.001 (2)
C21	0.053 (3)	0.053 (3)	0.035 (2)	0.004 (2)	0.002 (2)	0.007 (2)

Geometric parameters (Å, º)

F—C21	1.387 (5)	C9—C10	1.541 (5)
O1—C15	1.412 (5)	C9—H9	0.98
O1—C12	1.439 (5)	C10—C20	1.541 (5)
O2—C17	1.186 (4)	C11—C12	1.532 (5)
O3—C17	1.386 (5)	C11—H11A	0.97
O3—C21	1.422 (4)	C11—H11B	0.97
C1—C2	1.530 (5)	C12—C13	1.532 (5)
C1—C10	1.532 (5)	C12—H12	0.98
C1—H1A	0.97	C13—C16	1.524 (6)
C1—H1B	0.97	C13—C14	1.525 (5)
C2—C3	1.517 (5)	C13—H13	0.98
C2—H2A	0.97	C14—C17	1.499 (5)
C2—H2B	0.97	C14—H14	0.98
C3—C4	1.539 (5)	C15—C16	1.520 (6)
C3—H3A	0.97	C15—H15A	0.97
C3—H3B	0.97	C15—H15B	0.97
C4—C18	1.530 (5)	C16—H16A	0.97
C4—C19	1.534 (6)	C16—H16B	0.97
C4—C5	1.534 (5)	C18—H18A	0.96
C5—C10	1.552 (5)	C18—H18B	0.96
C5—C6	1.552 (4)	C18—H18C	0.96
C5—H5	0.98	C19—H19A	0.96
C6—C21	1.511 (5)	C19—H19B	0.96
C6—C8	1.538 (5)	C19—H19C	0.96
C6—H6	0.98	C20—H20A	0.96
C8—C14	1.514 (5)	C20—H20B	0.96
C8—C9	1.531 (4)	C20—H20C	0.96
C8—H8	0.98	C21—H21	0.98
C9—C11	1.523 (5)
C15—O1—C12	109.0 (3)	C12—C11—H11B	109.7
C17—O3—C21	119.9 (3)	H11A—C11—H11B	108.2
C2—C1—C10	111.2 (3)	O1—C12—C13	103.2 (3)
C2—C1—H1A	109.4	O1—C12—C11	108.7 (3)
C10—C1—H1A	109.4	C13—C12—C11	118.9 (3)
C2—C1—H1B	109.4	O1—C12—H12	108.5
C10—C1—H1B	109.4	C13—C12—H12	108.5
H1A—C1—H1B	108	C11—C12—H12	108.5
C3—C2—C1	111.9 (3)	C16—C13—C14	113.6 (4)
C3—C2—H2A	109.2	C16—C13—C12	100.6 (3)
C1—C2—H2A	109.2	C14—C13—C12	111.3 (3)
C3—C2—H2B	109.2	C16—C13—H13	110.3
C1—C2—H2B	109.2	C14—C13—H13	110.3
H2A—C2—H2B	107.9	C12—C13—H13	110.3
C2—C3—C4	116.3 (3)	C17—C14—C8	108.2 (3)
C2—C3—H3A	108.2	C17—C14—C13	115.2 (3)
C4—C3—H3A	108.2	C8—C14—C13	109.7 (3)
C2—C3—H3B	108.2	C17—C14—H14	107.8
C4—C3—H3B	108.2	C8—C14—H14	107.8
H3A—C3—H3B	107.4	C13—C14—H14	107.8
C18—C4—C19	107.2 (3)	O1—C15—C16	107.8 (4)
C18—C4—C5	110.1 (3)	O1—C15—H15A	110.2
C19—C4—C5	114.6 (3)	C16—C15—H15A	110.2
C18—C4—C3	108.3 (3)	O1—C15—H15B	110.2
C19—C4—C3	110.9 (3)	C16—C15—H15B	110.2
C5—C4—C3	105.7 (3)	H15A—C15—H15B	108.5
C4—C5—C10	117.5 (3)	C15—C16—C13	102.4 (3)
C4—C5—C6	121.7 (3)	C15—C16—H16A	111.3
C10—C5—C6	103.9 (3)	C13—C16—H16A	111.3
C4—C5—H5	103.9	C15—C16—H16B	111.3
C10—C5—H5	103.9	C13—C16—H16B	111.3
C6—C5—H5	103.9	H16A—C16—H16B	109.2
C21—C6—C8	110.3 (3)	O2—C17—O3	117.2 (4)
C21—C6—C5	118.0 (3)	O2—C17—C14	128.4 (4)
C8—C6—C5	103.8 (3)	O3—C17—C14	114.4 (3)
C21—C6—H6	108.1	C4—C18—H18A	109.5
C8—C6—H6	108.1	C4—C18—H18B	109.5
C5—C6—H6	108.1	H18A—C18—H18B	109.5
C14—C8—C9	109.3 (3)	C4—C18—H18C	109.5
C14—C8—C6	115.6 (3)	H18A—C18—H18C	109.5
C9—C8—C6	106.4 (3)	H18B—C18—H18C	109.5
C14—C8—H8	108.4	C4—C19—H19A	109.5
C9—C8—H8	108.4	C4—C19—H19B	109.5
C6—C8—H8	108.4	H19A—C19—H19B	109.5
C11—C9—C8	108.2 (3)	C4—C19—H19C	109.5
C11—C9—C10	124.5 (3)	H19A—C19—H19C	109.5
C8—C9—C10	102.2 (3)	H19B—C19—H19C	109.5
C11—C9—H9	107	C10—C20—H20A	109.5
C8—C9—H9	107	C10—C20—H20B	109.5
C10—C9—H9	107	H20A—C20—H20B	109.5
C1—C10—C9	114.8 (3)	C10—C20—H20C	109.5
C1—C10—C20	109.7 (3)	H20A—C20—H20C	109.5
C9—C10—C20	109.4 (3)	H20B—C20—H20C	109.5
C1—C10—C5	108.4 (3)	F—C21—O3	107.7 (3)
C9—C10—C5	98.6 (2)	F—C21—C6	110.6 (3)
C20—C10—C5	115.9 (3)	O3—C21—C6	112.0 (3)
C9—C11—C12	109.8 (3)	F—C21—H21	108.8
C9—C11—H11A	109.7	O3—C21—H21	108.8
C12—C11—H11A	109.7	C6—C21—H21	108.8
C9—C11—H11B	109.7
C10—C1—C2—C3	−54.7 (5)	C4—C5—C10—C20	67.3 (4)
C1—C2—C3—C4	54.6 (5)	C6—C5—C10—C20	−70.4 (4)
C2—C3—C4—C18	−168.4 (4)	C8—C9—C11—C12	55.0 (4)
C2—C3—C4—C19	74.3 (4)	C10—C9—C11—C12	174.7 (3)
C2—C3—C4—C5	−50.5 (5)	C15—O1—C12—C13	−30.4 (4)
C18—C4—C5—C10	169.1 (3)	C15—O1—C12—C11	−157.5 (3)
C19—C4—C5—C10	−70.0 (4)	C9—C11—C12—O1	74.1 (4)
C3—C4—C5—C10	52.5 (4)	C9—C11—C12—C13	−43.5 (5)
C18—C4—C5—C6	−61.1 (4)	O1—C12—C13—C16	40.7 (4)
C19—C4—C5—C6	59.7 (4)	C11—C12—C13—C16	161.0 (4)
C3—C4—C5—C6	−177.8 (3)	O1—C12—C13—C14	−80.0 (4)
C4—C5—C6—C21	75.9 (5)	C11—C12—C13—C14	40.4 (5)
C10—C5—C6—C21	−148.8 (3)	C9—C8—C14—C17	−168.3 (3)
C4—C5—C6—C8	−161.8 (3)	C6—C8—C14—C17	−48.2 (4)
C10—C5—C6—C8	−26.4 (4)	C9—C8—C14—C13	65.3 (4)
C21—C6—C8—C14	1.8 (5)	C6—C8—C14—C13	−174.7 (3)
C5—C6—C8—C14	−125.6 (3)	C16—C13—C14—C17	75.8 (4)
C21—C6—C8—C9	123.3 (3)	C12—C13—C14—C17	−171.5 (4)
C5—C6—C8—C9	−4.0 (4)	C16—C13—C14—C8	−161.9 (3)
C14—C8—C9—C11	−68.6 (4)	C12—C13—C14—C8	−49.1 (4)
C6—C8—C9—C11	165.9 (3)	C12—O1—C15—C16	7.3 (4)
C14—C8—C9—C10	158.5 (3)	O1—C15—C16—C13	18.9 (5)
C6—C8—C9—C10	33.0 (4)	C14—C13—C16—C15	83.5 (4)
C2—C1—C10—C9	163.0 (3)	C12—C13—C16—C15	−35.6 (4)
C2—C1—C10—C20	−73.4 (4)	C21—O3—C17—O2	175.2 (4)
C2—C1—C10—C5	53.9 (4)	C21—O3—C17—C14	−2.7 (6)
C11—C9—C10—C1	74.7 (5)	C8—C14—C17—O2	−127.6 (5)
C8—C9—C10—C1	−162.9 (3)	C13—C14—C17—O2	−4.4 (7)
C11—C9—C10—C20	−49.1 (5)	C8—C14—C17—O3	50.1 (5)
C8—C9—C10—C20	73.3 (4)	C13—C14—C17—O3	173.2 (4)
C11—C9—C10—C5	−170.4 (3)	C17—O3—C21—F	73.8 (4)
C8—C9—C10—C5	−48.0 (3)	C17—O3—C21—C6	−48.0 (5)
C4—C5—C10—C1	−56.5 (4)	C8—C6—C21—F	−74.4 (4)
C6—C5—C10—C1	165.9 (3)	C5—C6—C21—F	44.6 (4)
C4—C5—C10—C9	−176.3 (3)	C8—C6—C21—O3	45.7 (4)
C6—C5—C10—C9	46.1 (3)	C5—C6—C21—O3	164.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3^i	0.98	2.65	3.449 (5)	139
C18—H18A···O2^ii	0.96	2.76	3.684 (5)	161
C21—H21···O2^ii	0.98	2.77	3.560 (6)	138
C20—H20A···F^iii	0.96	2.68	3.619 (4)	166

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