20-Hydroxy­imino-5[alpha]-pregna-9(11),16-dien-3[beta]-yl acetate and 17-oxo-5[alpha]-androst-9(11)-en-3[beta]-yl acetate

In the title compounds, C₂₃H₃₃NO₃ and C₂₁H₃₀O₃, respectively, the ester linkage in ring A is equatorial. In these steroids, the six-membered rings A and B have chair conformations, but ring C can be better described as a half-chair. The five-membered ring D adopts a 14[alpha]-envelop conformation. The A/B, B/C and C/D ring junctions are trans.

S1. Comment

Corticosteroids have demonstrated substantial topical anti-inflammatory potency. In particular, betamethasone 17-benzoate has been in clinical practice for a long time (Lutsky et al., 1979). The strategy and importance for the synthesis of these compounds have their antecedents in similar structures, with anabolic and/or androgenic activity, replacing the positions 9α and 11β with fluorine and hydroxyl, respectively (Shapiro et al., 1987). An example of this is the 9α-fluoro-11β,17α-dihydroxy-17α-methyl-4-androsten-3-one (halotestin), a commercial compound 20 times more androgenic and 10 times more anabolic than methyltestosterone. In connection with our studies on the synthesis and characterization of bioactive steroids, the structures of the obtained compounds (I) and (II) could allow us to predict the possibility of presenting/displaying anabolic and/or androgenic properties. \scheme

The absolute configuration was assumed to be the same as the one predicted beforehand from the synthesis route; it was not reliably determined from the X-ray data. The C3—O31 bond of the acetoxy group is equatorially oriented and (-)antiperiplanar to the C3—C4 bond for both compounds. The presence of the acetoxy bounded to C3 does not disturb the chair conformation in the ring A of the steroidal nucleus. Ring A has a highly symmetrical chair conformation with all asymmetry parameters (Duax et al., 1976) below 8.3 (3)° [2.4 (4)°, for compound (II)]. Rotational symmetry is dominant, a pseudo-C₂ axis intercepts the C3—C4 bond with asymmetry parameters ΔC₂(C3—C4) = 3.3 (3), ΔC_S(C1) = 5.3 (2) and ΔC_S(C3) = 1.4 (2)° [for compound (II): ΔC₂(C3—C4) = 1.5 (5), ΔC_S(C1) = 1.6 (4) and ΔC_S(C3) = 0.6 (4)°]. The average magnitude of the torsion angles is 55.1 (1)° [55.6 (2)°]. Ring B in both structures displays a chair conformation, as expected (Pfieffer et al., 1985), but this is not the case for ring C which has a half-chair conformation. The five-membered ring D, in both structures, adopts a 14α-envelope conformation (Altona et al., 1968). The A/B, B/C and C/D ring junctions are trans. Bond distances and valence angles are close to expected values (Honda et al. 1996). In compound (I), the packing of the molecules is assumed to be dictated mainly by intermolecular hydrogen bonds O—H···O. There is an intramolecular C—H···O interactions between the O17 atom of the oxime group and the terminal C172 atom of the methyl group (Taylor & Kennard, 1982). The molecules are linked forming an infinite one-dimensional network with base vector [001], by means of the O—H···O hydrogen bonds. There are no intermolecular hydrogen bonds present in the compound (II); however, an intermolecular C—H···O interaction between the atom O32 of the acetoxy group and the carbon C15 is present (Taylor & Kennard, 1982). The packing of the molecules is assumed to be dictated by this interaction and van der Waals forces in (II).

S2. Experimental

The synthesis of (I) and (II) is described by Ruíz (1997). M.p.: 536–538 K for (I) and 469–479 K for (II). Crystals were grown from ethanol by slow evaporation.

Computing details

For both compounds, data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: PLATON (Spek, 1990), PARST (Nardelli, 1983, 1995) and PARSTCIF (Nardelli, 1991).

(I) 5α-9(11)(16)-pregnadien-3β-ol-20-oxime acetate

Crystal data

C23H33NO3	Dx = 1.186 Mg m^−3
Mr = 371.51	Cu Kα radiation, λ = 1.54180 Å
Orthorhombic, P212121	Cell parameters from 46 reflections
a = 7.0198 (2) Å	θ = 7.4–34.2°
b = 12.0153 (5) Å	µ = 0.61 mm^−1
c = 24.669 (2) Å	T = 293 K
V = 2080.7 (2) Å^3	Block, colourless
Z = 4	0.38 × 0.30 × 0.20 mm
F(000) = 808

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.022
ω/2θ scans	θmax = 69.2°
Absorption correction: ψ scan (North et al., 1968)	h = −1→7
Tmin = 0.765, Tmax = 0.885	k = −1→14
2846 measured reflections	l = −29→1
2614 independent reflections	3 standard reflections every 100 reflections
2318 reflections with F^2 > 2σ(F^2)	intensity decay: 0.0%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0605P)^2 + 0.2543P] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max = 0.001
R[F^2 > 2σ(F^2)] = 0.039	Δρmax = 0.15 e Å^−3
wR(F^2) = 0.111	Δρmin = −0.12 e Å^−3
S = 1.06	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin((2θ)]^-1/4
2614 reflections	Extinction coefficient: 0.0039 (4)
250 parameters	Absolute structure: Flack (1983), 227 Friedel pairs
H-atom parameters constrained	Absolute structure parameter: 0.1 (5)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
C1	0.3880 (4)	0.9005 (2)	0.76941 (9)	0.0483 (8)*
C2	0.3250 (4)	0.9025 (2)	0.82928 (9)	0.0511 (8)*
C3	0.3601 (4)	0.7922 (2)	0.85715 (9)	0.0493 (8)*
O31	0.3434 (3)	0.8041 (2)	0.91615 (6)	0.0592 (6)*
C31	0.1732 (4)	0.8186 (2)	0.9387 (1)	0.0559 (9)*
O32	0.0268 (3)	0.8168 (2)	0.91323 (8)	0.0732 (8)*
C32	0.1857 (5)	0.8363 (3)	0.9987 (1)	0.081 (1)*
C4	0.5590 (4)	0.7499 (2)	0.84836 (9)	0.0487 (8)*
C5	0.6210 (4)	0.7509 (2)	0.78885 (9)	0.0418 (8)*
C6	0.8186 (4)	0.7038 (2)	0.7819 (1)	0.0540 (9)*
C7	0.8748 (4)	0.6972 (2)	0.72286 (9)	0.0528 (8)*
C8	0.8553 (4)	0.8089 (2)	0.69351 (8)	0.0407 (7)*
C9	0.6609 (4)	0.8620 (2)	0.70305 (8)	0.0393 (7)*
C10	0.5971 (4)	0.8682 (2)	0.76287 (9)	0.0372 (6)*
C11	0.5675 (4)	0.9116 (2)	0.66255 (9)	0.0448 (7)*
C12	0.6349 (4)	0.9239 (2)	0.60451 (9)	0.0453 (7)*
C13	0.8492 (4)	0.9010 (2)	0.60067 (8)	0.0386 (7)*
C14	0.8864 (4)	0.7943 (2)	0.63341 (9)	0.0418 (7)*
C15	1.0768 (4)	0.7504 (2)	0.6123 (1)	0.0597 (9)*
C16	1.0695 (4)	0.7893 (2)	0.5548 (1)	0.061 (1)*
C17	0.9396 (4)	0.8682 (2)	0.54646 (9)	0.0449 (6)*
C171	0.9084 (4)	0.9222 (2)	0.49396 (9)	0.0468 (8)*
N17	0.7764 (4)	0.9960 (2)	0.49128 (8)	0.0537 (7)*
O17	0.7626 (4)	1.0383 (2)	0.43811 (7)	0.0721 (8)*
C172	1.0264 (5)	0.8888 (3)	0.4462 (1)	0.071 (1)*
C18	0.9584 (5)	1.0023 (2)	0.6219 (1)	0.0546 (9)*
C19	0.7241 (4)	0.9571 (2)	0.79038 (9)	0.0523 (9)*
H1A	0.3094	0.8479	0.7497	0.060*
H1B	0.3679	0.9736	0.7537	0.060*
H2A	0.3942	0.9605	0.8482	0.064*
H2B	0.1903	0.9201	0.8312	0.064*
H3	0.2681	0.7369	0.8442	0.062*
H32A	0.0825	0.8830	1.0103	0.101*
H32B	0.3047	0.8714	1.0074	0.101*
H32C	0.1778	0.7658	1.0169	0.101*
H4A	0.5674	0.6744	0.8620	0.061*
H4B	0.6466	0.7954	0.8692	0.061*
H5	0.5343	0.7009	0.7695	0.052*
H6A	0.8236	0.6299	0.7978	0.067*
H6B	0.9091	0.7504	0.8011	0.067*
H7A	0.7952	0.6424	0.7049	0.066*
H7B	1.0058	0.6721	0.7203	0.066*
H8	0.9533	0.8594	0.7074	0.051*
H11	0.4489	0.9416	0.6708	0.056*
H12A	0.6084	0.9987	0.5918	0.057*
H12B	0.5664	0.8721	0.5815	0.057*
H14	0.7902	0.7406	0.6214	0.052*
H15A	1.1835	0.7829	0.6317	0.075*
H15B	1.0839	0.6699	0.6146	0.075*
H16	1.1477	0.7613	0.5276	0.076*
H17	0.6668	1.0769	0.4355	0.090*
H17A	0.9616	0.9092	0.4134	0.088*
H17B	1.0461	0.8098	0.4468	0.088*
H17C	1.1472	0.9261	0.4478	0.088*
H18A	0.9474	1.0624	0.5964	0.068*
H18B	1.0903	0.9833	0.6264	0.068*
H18C	0.9061	1.0249	0.6561	0.068*
H19A	0.6964	1.0289	0.7753	0.065*
H19B	0.8558	0.9394	0.7843	0.065*
H19C	0.6990	0.9581	0.8286	0.065*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.048 (2)	0.054 (1)	0.043 (1)	0.013 (1)	−0.002 (1)	0.005 (1)
C2	0.046 (2)	0.062 (1)	0.045 (1)	0.010 (1)	0.004 (1)	0.005 (1)
C3	0.047 (2)	0.061 (1)	0.040 (1)	−0.005 (1)	−0.005 (1)	0.007 (1)
O31	0.046 (1)	0.089 (1)	0.0422 (9)	−0.001 (1)	0.0010 (8)	0.0138 (9)
C31	0.050 (2)	0.065 (2)	0.053 (1)	−0.003 (2)	0.005 (1)	0.005 (1)
O32	0.049 (1)	0.106 (2)	0.064 (1)	0.004 (1)	0.002 (1)	−0.011 (1)
C32	0.076 (2)	0.121 (3)	0.047 (1)	0.004 (2)	0.005 (2)	0.010 (2)
C4	0.049 (2)	0.053 (1)	0.045 (1)	0.000 (1)	−0.005 (1)	0.013 (1)
C5	0.041 (1)	0.041 (1)	0.043 (1)	0.001 (1)	−0.008 (1)	0.0051 (9)
C6	0.055 (2)	0.054 (1)	0.053 (1)	0.013 (1)	−0.004 (1)	0.014 (1)
C7	0.056 (2)	0.048 (1)	0.055 (1)	0.019 (1)	0.000 (1)	0.007 (1)
C8	0.040 (1)	0.040 (1)	0.042 (1)	0.004 (1)	−0.009 (1)	−0.0012 (9)
C9	0.039 (1)	0.040 (1)	0.039 (1)	0.004 (1)	−0.004 (1)	−0.0005 (9)
C10	0.040 (1)	0.0356 (9)	0.036 (1)	0.002 (1)	−0.0044 (9)	0.0006 (8)
C11	0.038 (1)	0.055 (1)	0.041 (1)	0.007 (1)	−0.002 (1)	0.004 (1)
C12	0.044 (1)	0.052 (1)	0.039 (1)	0.009 (1)	−0.003 (1)	0.002 (1)
C13	0.042 (1)	0.037 (1)	0.037 (1)	0.003 (1)	−0.001 (1)	−0.0043 (9)
C14	0.042 (1)	0.039 (1)	0.044 (1)	0.006 (1)	−0.003 (1)	−0.0026 (9)
C15	0.062 (2)	0.063 (2)	0.054 (2)	0.026 (2)	0.004 (1)	−0.001 (1)
C16	0.063 (2)	0.068 (2)	0.051 (1)	0.021 (2)	0.011 (1)	−0.007 (1)
C17	0.046 (1)	0.046 (1)	0.042 (1)	0.004 (1)	0.005 (1)	−0.005 (1)
C171	0.049 (2)	0.050 (1)	0.041 (1)	−0.002 (1)	0.006 (1)	−0.004 (1)
N17	0.058 (1)	0.065 (1)	0.0383 (9)	0.004 (1)	0.005 (1)	0.0074 (9)
O17	0.081 (2)	0.088 (2)	0.0469 (9)	0.019 (1)	0.009 (1)	0.019 (1)
C172	0.083 (2)	0.075 (2)	0.054 (2)	0.017 (2)	0.023 (2)	0.005 (1)
C18	0.062 (2)	0.049 (1)	0.053 (1)	−0.011 (1)	−0.001 (1)	−0.008 (1)
C19	0.061 (2)	0.051 (1)	0.045 (1)	−0.011 (1)	−0.001 (1)	−0.007 (1)

Geometric parameters (Å, º)

O17—N17	1.410 (3)	C2—H2A	0.9695
O31—C3	1.467 (3)	C2—H2B	0.9702
O31—C31	1.329 (3)	C3—H3	0.9804
O32—C31	1.204 (3)	C4—H4A	0.9706
O17—H17	0.8198	C4—H4B	0.9695
N17—C171	1.285 (4)	C5—H5	0.9798
C1—C10	1.527 (3)	C6—H6A	0.9701
C1—C2	1.542 (3)	C6—H6B	0.9702
C2—C3	1.513 (3)	C7—H7B	0.9701
C3—C4	1.501 (4)	C7—H7A	0.9703
C4—C5	1.531 (3)	C8—H8	0.9799
C5—C6	1.508 (4)	C11—H11	0.9299
C5—C10	1.557 (3)	C12—H12A	0.9699
C6—C7	1.512 (3)	C12—H12B	0.9700
C7—C8	1.531 (3)	C14—H14	0.9798
C8—C9	1.525 (3)	C15—H15A	0.9701
C8—C14	1.509 (3)	C15—H15B	0.9698
C9—C11	1.335 (3)	C16—H16	0.9300
C9—C10	1.544 (3)	C18—H18A	0.9602
C10—C19	1.548 (3)	C18—H18B	0.9600
C11—C12	1.515 (3)	C18—H18C	0.9602
C12—C13	1.532 (4)	C19—H19A	0.9598
C13—C14	1.537 (3)	C19—H19B	0.9602
C13—C17	1.532 (3)	C19—H19C	0.9600
C13—C18	1.531 (3)	C32—H32C	0.9599
C14—C15	1.528 (4)	C32—H32A	0.9601
C15—C16	1.496 (4)	C32—H32B	0.9599
C16—C17	1.331 (4)	C171—C172	1.495 (4)
C17—C171	1.465 (3)	C172—H17A	0.9598
C31—C32	1.500 (3)	C172—H17B	0.9606
C1—H1B	0.9702	C172—H17C	0.9596
C1—H1A	0.9700
C3—O31—C31	119.9 (2)	H4A—C4—H4B	107.68
N17—O17—H17	109.49	C6—C5—H5	106.64
O17—N17—C171	110.2 (2)	C10—C5—H5	106.68
C2—C1—C10	112.4 (2)	C4—C5—H5	106.70
C1—C2—C3	112.0 (2)	H6A—C6—H6B	107.94
O31—C3—C2	110.62 (19)	C5—C6—H6B	109.30
O31—C3—C4	104.51 (19)	C7—C6—H6A	109.31
C2—C3—C4	112.4 (2)	C5—C6—H6A	109.31
C3—C4—C5	113.6 (2)	C7—C6—H6B	109.27
C4—C5—C6	111.6 (2)	C8—C7—H7A	109.06
C6—C5—C10	113.1 (2)	C8—C7—H7B	109.06
C4—C5—C10	111.72 (19)	C6—C7—H7B	109.05
C5—C6—C7	111.6 (2)	C6—C7—H7A	109.03
C6—C7—C8	112.74 (19)	H7A—C7—H7B	107.78
C7—C8—C14	110.49 (18)	C7—C8—H8	108.34
C9—C8—C14	109.25 (19)	C9—C8—H8	108.33
C7—C8—C9	112.0 (2)	C14—C8—H8	108.36
C8—C9—C11	120.71 (19)	C12—C11—H11	116.66
C10—C9—C11	123.5 (2)	C9—C11—H11	116.66
C8—C9—C10	115.28 (17)	C11—C12—H12A	109.60
C1—C10—C9	113.08 (18)	C11—C12—H12B	109.60
C1—C10—C19	109.37 (18)	C13—C12—H12A	109.57
C1—C10—C5	106.87 (19)	C13—C12—H12B	109.57
C5—C10—C19	112.47 (18)	H12A—C12—H12B	108.13
C9—C10—C19	106.55 (17)	C15—C14—H14	105.84
C5—C10—C9	108.59 (17)	C13—C14—H14	105.86
C9—C11—C12	126.7 (2)	C8—C14—H14	105.86
C11—C12—C13	110.3 (2)	C14—C15—H15A	111.64
C12—C13—C14	106.50 (18)	C14—C15—H15B	111.65
C12—C13—C17	120.46 (19)	C16—C15—H15A	111.62
C14—C13—C17	100.01 (17)	C16—C15—H15B	111.64
C14—C13—C18	113.47 (18)	H15A—C15—H15B	109.43
C12—C13—C18	109.1 (2)	C17—C16—H16	123.46
C17—C13—C18	107.19 (19)	C15—C16—H16	123.46
C8—C14—C15	120.1 (2)	C13—C18—H18A	109.48
C13—C14—C15	104.94 (19)	H18B—C18—H18C	109.47
C8—C14—C13	113.26 (18)	C13—C18—H18C	109.49
C14—C15—C16	100.7 (2)	H18A—C18—H18B	109.45
C15—C16—C17	113.1 (2)	C13—C18—H18B	109.49
C13—C17—C16	109.4 (2)	H18A—C18—H18C	109.44
C13—C17—C171	126.6 (2)	H19A—C19—H19B	109.46
C16—C17—C171	123.6 (2)	H19A—C19—H19C	109.48
O31—C31—C32	112.3 (2)	C10—C19—H19C	109.49
O32—C31—C32	124.5 (3)	C10—C19—H19A	109.50
O31—C31—O32	123.2 (2)	C10—C19—H19B	109.46
H1A—C1—H1B	107.84	H19B—C19—H19C	109.44
C2—C1—H1B	109.09	H32A—C32—H32C	109.46
C10—C1—H1B	109.14	H32B—C32—H32C	109.50
C2—C1—H1A	109.12	H32A—C32—H32B	109.47
C10—C1—H1A	109.16	C31—C32—H32A	109.45
C1—C2—H2A	109.25	C31—C32—H32B	109.46
C1—C2—H2B	109.22	C31—C32—H32C	109.48
C3—C2—H2A	109.19	N17—C171—C17	117.3 (2)
C3—C2—H2B	109.16	N17—C171—C172	123.0 (2)
H2A—C2—H2B	107.92	C17—C171—C172	119.7 (2)
C4—C3—H3	109.69	C171—C172—H17A	109.47
C2—C3—H3	109.75	C171—C172—H17B	109.47
O31—C3—H3	109.71	C171—C172—H17C	109.49
C3—C4—H4A	108.82	H17A—C172—H17B	109.43
C3—C4—H4B	108.85	H17A—C172—H17C	109.52
C5—C4—H4A	108.82	H17B—C172—H17C	109.46
C5—C4—H4B	108.89
C31—O31—C3—C4	−166.5 (2)	C8—C9—C11—C12	−0.8 (4)
C3—O31—C31—O32	4.0 (4)	C11—C9—C10—C1	19.7 (3)
C3—O31—C31—C32	−176.4 (2)	C10—C9—C11—C12	170.4 (2)
C31—O31—C3—C2	72.3 (3)	C8—C9—C10—C19	71.1 (2)
O17—N17—C171—C172	0.0 (4)	C11—C9—C10—C19	−100.5 (3)
O17—N17—C171—C17	−179.0 (2)	C11—C9—C10—C5	138.1 (2)
C10—C1—C2—C3	−56.4 (3)	C9—C11—C12—C13	−15.8 (3)
C2—C1—C10—C5	58.7 (2)	C11—C12—C13—C17	158.7 (2)
C2—C1—C10—C19	−63.3 (2)	C11—C12—C13—C14	46.1 (2)
C2—C1—C10—C9	178.13 (18)	C11—C12—C13—C18	−76.7 (2)
C1—C2—C3—C4	49.8 (3)	C18—C13—C14—C8	52.5 (3)
C1—C2—C3—O31	166.2 (2)	C12—C13—C14—C8	−67.6 (3)
C2—C3—C4—C5	−49.7 (3)	C18—C13—C14—C15	−80.3 (2)
O31—C3—C4—C5	−169.69 (19)	C17—C13—C14—C8	166.3 (2)
C3—C4—C5—C6	−177.9 (2)	C17—C13—C14—C15	33.6 (2)
C3—C4—C5—C10	54.5 (3)	C18—C13—C17—C171	−78.6 (3)
C6—C5—C10—C1	175.85 (19)	C12—C13—C17—C171	46.8 (3)
C4—C5—C10—C19	62.7 (3)	C12—C13—C14—C15	159.65 (18)
C10—C5—C6—C7	−57.0 (3)	C12—C13—C17—C16	−140.0 (2)
C4—C5—C10—C1	−57.3 (3)	C18—C13—C17—C16	94.6 (2)
C4—C5—C10—C9	−179.6 (2)	C14—C13—C17—C171	162.8 (3)
C6—C5—C10—C9	53.6 (2)	C14—C13—C17—C16	−23.9 (3)
C4—C5—C6—C7	176.1 (2)	C13—C14—C15—C16	−31.1 (2)
C6—C5—C10—C19	−64.1 (2)	C8—C14—C15—C16	−159.9 (2)
C5—C6—C7—C8	54.3 (3)	C14—C15—C16—C17	16.9 (3)
C6—C7—C8—C14	−172.1 (2)	C15—C16—C17—C13	4.7 (3)
C6—C7—C8—C9	−50.1 (3)	C15—C16—C17—C171	178.2 (2)
C7—C8—C9—C11	−138.6 (2)	C16—C17—C171—N17	179.0 (3)
C7—C8—C9—C10	49.5 (2)	C16—C17—C171—C172	0.0 (4)
C14—C8—C9—C10	172.29 (18)	C13—C17—C171—C172	172.3 (3)
C7—C8—C14—C15	−60.8 (3)	C13—C17—C171—N17	−8.7 (4)
C14—C8—C9—C11	−15.8 (3)	N17—C171—C172—H17A	−20.15
C9—C8—C14—C15	175.6 (2)	N17—C171—C172—H17B	−140.09
C7—C8—C14—C13	174.2 (2)	N17—C171—C172—H17C	99.91
C9—C8—C14—C13	50.6 (3)	C17—C171—C172—H17A	158.80
C8—C9—C10—C1	−168.68 (19)	C17—C171—C172—H17B	38.86
C8—C9—C10—C5	−50.2 (2)	C17—C171—C172—H17C	−81.13

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O17—H17···O32^i	0.82	1.94	2.745 (3)	165
C172—H17A···O17	0.96	2.17	2.586 (4)	104

Symmetry code: (i) −x+1/2, −y+2, z−1/2.

(II) 5α-9(11)-androsten-3β-ol-17-one acetate

Crystal data

C21H30O3	F(000) = 360
Mr = 330.45	Dx = 1.154 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54180 Å
a = 10.112 (1) Å	Cell parameters from 36 reflections
b = 7.7821 (6) Å	θ = 11.0–23.5°
c = 12.0922 (9) Å	µ = 0.59 mm^−1
β = 91.73 (1)°	T = 293 K
V = 951.1 (1) Å^3	Plate, colourless
Z = 2	0.44 × 0.30 × 0.02 mm

Data collection

Siemens P4 four-circle diffractometer	Rint = 0.024
ω/2θ scans	θmax = 68.8°
Absorption correction: ψscan (North et al., 1968)	h = −1→12
Tmin = 0.825, Tmax = 0.988	k = −8→1
2465 measured reflections	l = −14→14
2109 independent reflections	3 standard reflections every 100 reflections
1395 reflections with F^2 > 2σ(F^2)	intensity decay: 0.0%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.0881P] where P = (Fo^2 + 2Fc^2)/3
Least-squares matrix: full	(Δ/σ)max = 0.001
R[F^2 > 2σ(F^2)] = 0.048	Δρmax = 0.17 e Å^−3
wR(F^2) = 0.147	Δρmin = −0.18 e Å^−3
S = 1.06	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin((2θ)]^-1/4
2109 reflections	Extinction coefficient: 0.0031 (9)
221 parameters	Absolute structure: Flack (1983), 501 Friedel pairs
H-atom parameters constrained	Absolute structure parameter: −0.3 (4)

Special details

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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

	x	y	z	Uiso*/Ueq
C1	0.3306 (5)	−0.0177 (5)	0.6005 (3)	0.060 (2)*
C2	0.3568 (5)	0.0081 (6)	0.7255 (3)	0.065 (2)*
C3	0.4248 (4)	0.1766 (5)	0.7456 (3)	0.052 (1)*
O31	0.4420 (3)	0.2112 (4)	0.8638 (2)	0.059 (1)*
C31	0.5410 (5)	0.1307 (6)	0.9164 (3)	0.059 (2)*
O32	0.6162 (4)	0.0348 (5)	0.8717 (2)	0.086 (1)*
C32	0.5509 (5)	0.1729 (8)	1.0366 (3)	0.081 (2)*
C4	0.3484 (4)	0.3252 (6)	0.6964 (3)	0.055 (1)*
C5	0.3235 (4)	0.2991 (5)	0.5725 (3)	0.047 (1)*
C6	0.2559 (5)	0.4531 (6)	0.5171 (3)	0.061 (2)*
C7	0.2427 (5)	0.4300 (6)	0.3928 (3)	0.058 (1)*
C8	0.1782 (4)	0.2615 (5)	0.3559 (3)	0.048 (1)*
C9	0.2403 (4)	0.1096 (6)	0.4185 (3)	0.048 (1)*
C10	0.2506 (4)	0.1281 (6)	0.5448 (3)	0.048 (1)*
C11	0.2731 (5)	−0.0345 (6)	0.3661 (3)	0.065 (2)*
C12	0.2553 (5)	−0.0681 (7)	0.2440 (3)	0.073 (2)*
C13	0.1519 (4)	0.0543 (6)	0.1944 (3)	0.056 (2)*
C14	0.1859 (4)	0.2361 (6)	0.2322 (3)	0.050 (1)*
C15	0.1067 (5)	0.3523 (8)	0.1527 (4)	0.072 (2)*
C16	0.1173 (5)	0.2582 (8)	0.0411 (4)	0.084 (2)*
O17	0.1822 (4)	−0.0350 (6)	0.0030 (2)	0.088 (1)*
C17	0.1541 (4)	0.0764 (7)	0.0694 (3)	0.064 (2)*
C18	0.0128 (5)	−0.0016 (9)	0.2223 (4)	0.093 (2)*
C19	0.1092 (4)	0.1248 (8)	0.5882 (3)	0.070 (2)*
H1A	0.4148	−0.0279	0.5647	0.073*
H1B	0.2832	−0.1249	0.5891	0.073*
H2A	0.27377	0.00598	0.76351	0.048 (2)*
H2B	0.4119	−0.0846	0.7544	0.060*
H3	0.51210	0.17266	0.71264	0.058 (2)*
H32A	0.57273	0.07101	1.07793	0.060 (2)*
H32B	0.46777	0.21741	1.06000	0.102 (4)*
H32C	0.6187	0.2577	1.0491	0.082*
H4A	0.39781	0.43065	0.70888	0.114 (4)*
H4B	0.2645	0.3359	0.7326	0.091*
H5	0.4109	0.2899	0.5401	0.091*
H6A	0.16874	0.46812	0.54706	0.062 (3)*
H6B	0.30694	0.55604	0.53345	0.048 (2)*
H7A	0.3300	0.4366	0.3621	0.063*
H7B	0.19082	0.52455	0.36220	0.073 (3)*
H8	0.0845	0.2667	0.3741	0.090*
H11	0.3102	−0.1222	0.4090	0.090*
H12A	0.22721	−0.18601	0.23193	0.085 (3)*
H12B	0.3388	−0.0517	0.2080	0.104*
H14	0.2790	0.2534	0.2148	0.104*
H15A	0.14514	0.46632	0.14965	0.100 (3)*
H15B	0.01529	0.36167	0.17418	0.052 (2)*
H16A	0.03354	0.26185	−0.00007	0.094 (4)*
H16B	0.1847	0.3108	−0.0033	0.116*
H18A	0.0055	−0.0078	0.3011	0.116*
H18B	−0.0050	−0.1126	0.1905	0.116*
H18C	−0.04997	0.08014	0.19272	0.063 (3)*
H19A	0.0562	0.2092	0.5496	0.087*
H19B	0.1117	0.1503	0.6660	0.087*
H19C	0.0714	0.0129	0.5763	0.087*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O17	0.100 (3)	0.108 (3)	0.0548 (16)	−0.012 (2)	0.0112 (16)	−0.012 (2)
O31	0.0744 (18)	0.059 (2)	0.0451 (14)	0.0073 (17)	0.0046 (13)	−0.0105 (14)
O32	0.110 (3)	0.079 (2)	0.0682 (18)	0.038 (2)	0.0028 (17)	−0.0056 (19)
C1	0.097 (3)	0.034 (2)	0.048 (2)	−0.004 (3)	0.001 (2)	0.0015 (19)
C2	0.097 (3)	0.046 (3)	0.051 (2)	−0.010 (3)	−0.004 (2)	0.002 (2)
C3	0.068 (3)	0.047 (3)	0.0407 (19)	−0.001 (2)	0.0051 (17)	−0.0055 (18)
C4	0.067 (3)	0.040 (3)	0.057 (2)	0.003 (2)	−0.001 (2)	−0.0098 (19)
C5	0.057 (2)	0.032 (2)	0.052 (2)	0.0004 (19)	0.0052 (17)	−0.0013 (18)
C6	0.078 (3)	0.039 (3)	0.066 (2)	0.005 (2)	−0.005 (2)	0.000 (2)
C7	0.076 (3)	0.035 (2)	0.063 (2)	0.000 (2)	−0.003 (2)	0.0053 (19)
C8	0.048 (2)	0.046 (3)	0.051 (2)	0.003 (2)	0.0058 (16)	0.0040 (18)
C9	0.058 (2)	0.039 (2)	0.0481 (19)	−0.002 (2)	0.0063 (16)	0.0002 (18)
C10	0.060 (2)	0.036 (2)	0.0472 (19)	−0.006 (2)	0.0063 (17)	−0.0031 (19)
C11	0.102 (4)	0.044 (3)	0.049 (2)	0.010 (3)	0.001 (2)	−0.001 (2)
C12	0.114 (4)	0.054 (3)	0.051 (2)	0.008 (3)	0.005 (2)	−0.002 (2)
C13	0.062 (3)	0.058 (3)	0.048 (2)	−0.014 (2)	0.0056 (18)	0.000 (2)
C14	0.048 (2)	0.056 (3)	0.048 (2)	−0.003 (2)	0.0013 (16)	0.0062 (19)
C15	0.074 (3)	0.075 (4)	0.068 (3)	0.016 (3)	−0.007 (2)	0.013 (3)
C16	0.085 (3)	0.108 (5)	0.058 (3)	0.007 (4)	−0.005 (2)	0.017 (3)
C17	0.051 (2)	0.087 (4)	0.054 (2)	−0.012 (3)	0.0025 (19)	0.002 (3)
C18	0.094 (4)	0.119 (5)	0.067 (3)	−0.058 (4)	0.022 (2)	−0.018 (3)
C19	0.063 (3)	0.088 (4)	0.059 (2)	−0.021 (3)	0.0148 (19)	−0.007 (3)
C31	0.083 (3)	0.045 (3)	0.050 (2)	0.001 (3)	0.002 (2)	−0.001 (2)
C32	0.116 (4)	0.077 (4)	0.049 (2)	0.006 (3)	−0.001 (2)	−0.005 (2)

Geometric parameters (Å, º)

O17—C17	1.221 (6)	C2—H2A	0.9694
O31—C3	1.461 (4)	C2—H2B	0.9704
O31—C31	1.326 (6)	C3—H3	0.9799
O32—C31	1.205 (6)	C4—H4A	0.9700
C1—C2	1.540 (5)	C4—H4B	0.9694
C1—C10	1.537 (6)	C5—H5	0.9799
C2—C3	1.497 (6)	C6—H6A	0.9700
C3—C4	1.503 (6)	C6—H6B	0.9701
C4—C5	1.527 (5)	C7—H7A	0.9695
C5—C6	1.525 (6)	C7—H7B	0.9699
C5—C10	1.553 (6)	C8—H8	0.9800
C6—C7	1.516 (5)	C11—H11	0.9301
C7—C8	1.526 (6)	C12—H12A	0.9695
C8—C9	1.528 (6)	C12—H12B	0.9704
C8—C14	1.513 (5)	C14—H14	0.9802
C9—C10	1.534 (5)	C15—H15A	0.9699
C9—C11	1.335 (6)	C15—H15B	0.9704
C10—C19	1.539 (6)	C16—H16A	0.9699
C11—C12	1.505 (5)	C16—H16B	0.9705
C12—C13	1.525 (7)	C18—H18A	0.9596
C13—C14	1.522 (6)	C18—H18B	0.9603
C13—C17	1.522 (5)	C18—H18C	0.9601
C13—C18	1.520 (7)	C19—H19A	0.9605
C14—C15	1.529 (6)	C19—H19B	0.9594
C15—C16	1.542 (7)	C19—H19C	0.9600
C16—C17	1.500 (8)	C32—H32A	0.9601
C31—C32	1.491 (5)	C32—H32B	0.9594
C1—H1A	0.9698	C32—H32C	0.9599
C1—H1B	0.9702
C3—O31—C31	116.6 (3)	C5—C4—H4A	109.46
C2—C1—C10	114.0 (3)	C5—C4—H4B	109.49
C1—C2—C3	109.8 (3)	H4A—C4—H4B	108.12
O31—C3—C2	111.2 (3)	C4—C5—H5	106.18
O31—C3—C4	106.8 (3)	C6—C5—H5	106.22
C2—C3—C4	112.4 (3)	C10—C5—H5	106.20
C3—C4—C5	110.7 (3)	C5—C6—H6A	109.33
C4—C5—C6	112.7 (3)	C5—C6—H6B	109.32
C4—C5—C10	112.9 (3)	C7—C6—H6A	109.31
C6—C5—C10	112.0 (3)	C7—C6—H6B	109.27
C5—C6—C7	111.6 (4)	H6A—C6—H6B	107.95
C6—C7—C8	114.6 (4)	C6—C7—H7A	108.64
C7—C8—C9	110.8 (3)	C6—C7—H7B	108.62
C7—C8—C14	111.5 (3)	C8—C7—H7A	108.61
C9—C8—C14	110.9 (3)	C8—C7—H7B	108.58
C8—C9—C10	115.8 (4)	H7A—C7—H7B	107.62
C8—C9—C11	121.3 (3)	C7—C8—H8	107.85
C10—C9—C11	122.7 (4)	C9—C8—H8	107.81
C1—C10—C5	107.3 (3)	C14—C8—H8	107.85
C1—C10—C9	112.7 (3)	C9—C11—H11	116.97
C1—C10—C19	108.7 (4)	C12—C11—H11	117.02
C5—C10—C9	108.2 (3)	C11—C12—H12A	109.77
C5—C10—C19	112.4 (4)	C11—C12—H12B	109.69
C9—C10—C19	107.6 (3)	C13—C12—H12A	109.76
C9—C11—C12	126.0 (4)	C13—C12—H12B	109.68
C11—C12—C13	109.7 (4)	H12A—C12—H12B	108.22
C12—C13—C14	108.5 (3)	C8—C14—H14	105.79
C12—C13—C17	115.5 (3)	C13—C14—H14	105.84
C12—C13—C18	111.2 (4)	C15—C14—H14	105.83
C14—C13—C17	100.6 (4)	C14—C15—H15A	111.23
C14—C13—C18	113.7 (4)	C14—C15—H15B	111.18
C17—C13—C18	107.1 (3)	C16—C15—H15A	111.27
C8—C14—C13	113.6 (3)	C16—C15—H15B	111.21
C8—C14—C15	120.2 (4)	H15A—C15—H15B	109.12
C13—C14—C15	104.6 (3)	C15—C16—H16A	110.65
C14—C15—C16	102.7 (4)	C15—C16—H16B	110.60
C15—C16—C17	105.8 (4)	C17—C16—H16A	110.58
O17—C17—C13	125.7 (5)	C17—C16—H16B	110.53
O17—C17—C16	125.5 (4)	H16A—C16—H16B	108.71
C13—C17—C16	108.8 (4)	C13—C18—H18A	109.51
O31—C31—O32	123.7 (3)	C13—C18—H18B	109.46
O31—C31—C32	112.9 (4)	C13—C18—H18C	109.46
O32—C31—C32	123.3 (4)	H18A—C18—H18B	109.48
C2—C1—H1A	108.76	H18A—C18—H18C	109.49
C2—C1—H1B	108.71	H18B—C18—H18C	109.43
C10—C1—H1A	108.79	C10—C19—H19A	109.44
C10—C1—H1B	108.76	C10—C19—H19B	109.50
H1A—C1—H1B	107.64	C10—C19—H19C	109.45
C1—C2—H2A	109.72	H19A—C19—H19B	109.48
C1—C2—H2B	109.66	H19A—C19—H19C	109.43
C3—C2—H2A	109.76	H19B—C19—H19C	109.52
C3—C2—H2B	109.70	C31—C32—H32A	109.43
H2A—C2—H2B	108.22	C31—C32—H32B	109.48
O31—C3—H3	108.78	C31—C32—H32C	109.42
C2—C3—H3	108.76	H32A—C32—H32B	109.51
C4—C3—H3	108.79	H32A—C32—H32C	109.47
C3—C4—H4A	109.49	H32B—C32—H32C	109.53
C3—C4—H4B	109.54
C3—O31—C31—C32	−179.8 (4)	C9—C8—C14—C13	43.0 (5)
C31—O31—C3—C4	−158.1 (4)	C7—C8—C9—C10	50.0 (5)
C3—O31—C31—O32	1.0 (7)	C8—C9—C10—C19	68.0 (5)
C31—O31—C3—C2	78.9 (5)	C8—C9—C10—C5	−53.7 (4)
C2—C1—C10—C5	54.1 (5)	C11—C9—C10—C19	−106.8 (5)
C2—C1—C10—C19	−67.6 (5)	C11—C9—C10—C1	13.0 (6)
C2—C1—C10—C9	173.2 (4)	C11—C9—C10—C5	131.6 (4)
C10—C1—C2—C3	−56.1 (5)	C8—C9—C10—C1	−172.2 (4)
C1—C2—C3—O31	175.6 (3)	C8—C9—C11—C12	0.1 (7)
C1—C2—C3—C4	55.9 (5)	C10—C9—C11—C12	174.6 (4)
C2—C3—C4—C5	−56.9 (4)	C9—C11—C12—C13	−20.3 (7)
O31—C3—C4—C5	−179.1 (3)	C11—C12—C13—C17	161.2 (4)
C3—C4—C5—C6	−175.4 (4)	C11—C12—C13—C18	−76.5 (5)
C3—C4—C5—C10	56.4 (4)	C11—C12—C13—C14	49.3 (5)
C4—C5—C6—C7	175.2 (4)	C12—C13—C14—C15	163.0 (3)
C4—C5—C10—C19	65.4 (4)	C18—C13—C14—C8	60.1 (5)
C6—C5—C10—C1	177.5 (3)	C18—C13—C14—C15	−72.8 (4)
C6—C5—C10—C9	55.6 (4)	C12—C13—C14—C8	−64.2 (4)
C6—C5—C10—C19	−63.1 (4)	C12—C13—C17—C16	−145.4 (4)
C10—C5—C6—C7	−56.1 (5)	C14—C13—C17—O17	150.5 (4)
C4—C5—C10—C1	−54.0 (4)	C12—C13—C17—O17	34.0 (6)
C4—C5—C10—C9	−175.9 (3)	C18—C13—C17—O17	−90.4 (5)
C5—C6—C7—C8	52.2 (5)	C18—C13—C17—C16	90.1 (5)
C6—C7—C8—C9	−47.9 (5)	C17—C13—C14—C15	41.3 (4)
C6—C7—C8—C14	−171.9 (4)	C14—C13—C17—C16	−28.9 (4)
C14—C8—C9—C10	174.3 (3)	C17—C13—C14—C8	174.2 (3)
C7—C8—C9—C11	−135.2 (4)	C8—C14—C15—C16	−167.6 (4)
C7—C8—C14—C15	−68.2 (5)	C13—C14—C15—C16	−38.5 (4)
C14—C8—C9—C11	−10.8 (6)	C14—C15—C16—C17	19.8 (5)
C7—C8—C14—C13	166.9 (4)	C15—C16—C17—O17	−173.7 (4)
C9—C8—C14—C15	167.8 (4)	C15—C16—C17—C13	5.8 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O32^i	0.97	2.49	3.163 (6)	126

Symmetry code: (i) −x+1, y+1/2, −z+1.