[(1R,4aS)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa­hydro­phen­an­thren-1-yl](piperidin-1-yl)methanone

The title compound, C₂₅H₃₇NO, has been synthesized from (+)-dehydro­abietic acid. The piperidine ring exhibits a classic chair conformation, whereas the two cyclohexane rings adopt chair and half-chair conformations. The two methyl groups directly attached to the tricyclic nucleus are on the same side of the tricyclic phenanthrene structure.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.134
• Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.03
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.68 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
ABSTY01_ALERT_1_G  Extra text has been found in the _exptl_absorpt_correction_type
            field, which should be only a single keyword. A literature
            citation should be included in the _exptl_absorpt_process_details
            field.
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           26.00
           From the CIF: _reflns_number_total               2339
           Count of symmetry unique reflns         2352
           Completeness (_total/calc)             99.45%
           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
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   7 ALERT level G = General alerts; check

   6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

S1. Comment

(+)Dehydroabietic acid is an abietane diterpenic resin acid which can be easily obtained from Pinus resin or commercial rosin (Halbrook & Lawrence, 1966). It is widely used as a starting material for the design and synthesis of biological compounds. Biological activities, such as anti-tumor (Wada et al., 1985), antimicrobial (Savluchinske et al., 1999), anti-inflammatory (Fernandez et al., 2001) and gastroprotective (Sepulveda et al., 2005) effects of dehydroabietic acid derivatives have been reported. Heterocyclic chemistry has attracted great interest in recent years, for those compounds containing heterocyclic rings often exhibit higher biological activities. Heterocyclic rings fused to the aromatic ring of dehydroabietic acid (Fonseca et al., 2004) have been successfully synthesized, and they exhibit antiviral activities against DNA and RNA. Considerable efforts have been devoted to the biological activities of heterocyclic derivatives of dehydroabietic acid, yet the crystal structure of such compounds have seldom been reported. In this work, we describe the crystal structure of the title compound. The overall geometry is comparable to that found for dehydroabietic N-methyl anilide (Rao et al., 2006). The tricyclic phenanthrene structure of the title compound exhibits the same conformation as dehydroabietic N-methyl anilide, which exhibited planar, classic chair and half-chair conformations, respectively. The two cyclohexane rings form a trans ring junction with two methyl groups on the same side of the tricyclic phenanthrene structure (Hamodrakas, et al., 1978). Apart from the planar conformation of the benzene ring, the piperidine ring of the title compound forms a classic chair conformation. The bond lengths and bond angles in the molecule are in normal ranges.

Related literature

For related literature, see: Fernandez et al. (2001); Fonseca et al. (2004); Halbrook & Lawrence (1966); Hamodrakas et al. (1978); Rao et al. (2006); Savluchinske et al. (1999); Sepulveda et al. (2005); Wada et al. (1985).

S2. Experimental

All chemicals purchased were of reagent grade and used without further purification. A mixture of (+)dehydroabietic acid (0.1 mol), phosphorus trichloride (6 ml) and chloroform (40 ml) were stirred at 333 K for 3 h, then the solvent was distilled off. The residue was slowly added to piperidine (0.2 mol) in toluene (60 ml) solution. After a further 24 h stirring at room temperature, the resulting mixture was filtered. The precipitate was washed with hydrochloric acid (5%) and water and the solvent was distilled off. Upon recrystallization from acetone, colorless crystals of the title compound were obtained (yield 54.7%, m.p. 342.5 K). Single crystals were grown from acetone.

S3. Refinement

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl H atoms, and C—H = 0.97–0.98 Å and U_iso(H) = 1.2U_eq(C) for all other H atoms. In the absence of significant anomalous scattering effects, all Friedel pairs were merged.

Computing details

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997a).

Figures

Fig. 1. The molecular structure of the title compound, with H atoms represented by small spheres of arbitrary radius and displacement ellipsoids at the 30% probability level.

[(1R,4aS)-7-Isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a- octahydrophenanthren-1-yl](piperidin-1-yl)methanone

Crystal data

C25H37NO	Dx = 1.165 Mg m^−3
Mr = 367.56	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 25 reflections
a = 10.612 (2) Å	θ = 10–13°
b = 11.566 (2) Å	µ = 0.07 mm^−1
c = 17.067 (3) Å	T = 293 K
V = 2094.8 (7) Å^3	Block, white
Z = 4	0.40 × 0.20 × 0.10 mm
F(000) = 808

Data collection

Enraf–Nonius CAD-4 diffractometer	1756 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.043
Graphite monochromator	θmax = 26.0°, θmin = 2.1°
ω/2θ scans	h = 0→13
Absorption correction: ψ scans (North et al., 1968)	k = 0→14
Tmin = 0.932, Tmax = 0.966	l = −21→21
4522 measured reflections	3 standard reflections every 200 reflections
2339 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.08P)^2 + 0.1P] where P = (Fo^2 + 2Fc^2)/3
2339 reflections	(Δ/σ)max < 0.001
245 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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	0.6299 (2)	0.8464 (2)	0.82631 (14)	0.0531 (6)
N1	0.7308 (3)	0.9998 (2)	0.77919 (15)	0.0441 (7)
C1	0.7437 (5)	0.1750 (3)	1.1017 (3)	0.0815 (14)
H1A	0.7027	0.1077	1.1227	0.122*
H1B	0.8050	0.2027	1.1386	0.122*
H1C	0.7848	0.1553	1.0535	0.122*
C2	0.5402 (4)	0.2221 (4)	1.0376 (3)	0.0845 (14)
H2A	0.5062	0.1541	1.0620	0.127*
H2B	0.5712	0.2028	0.9864	0.127*
H2C	0.4754	0.2796	1.0331	0.127*
C3	0.6465 (4)	0.2686 (3)	1.0868 (2)	0.0586 (10)
H3	0.6106	0.2895	1.1377	0.070*
C4	0.7086 (3)	0.3767 (3)	1.0541 (2)	0.0455 (8)
C5	0.7801 (4)	0.4453 (3)	1.1025 (2)	0.0549 (9)
H5	0.7889	0.4248	1.1550	0.066*
C6	0.8393 (3)	0.5436 (3)	1.07563 (19)	0.0484 (8)
H6	0.8881	0.5871	1.1101	0.058*
C7	0.8278 (3)	0.5796 (3)	0.99782 (17)	0.0361 (7)
C8	0.8948 (3)	0.6890 (2)	0.96851 (17)	0.0351 (7)
C9	0.9003 (3)	0.7812 (3)	1.03387 (18)	0.0416 (8)
H9A	0.8172	0.7902	1.0567	0.050*
H9B	0.9570	0.7551	1.0748	0.050*
C10	0.9451 (3)	0.8968 (3)	1.00311 (19)	0.0450 (8)
H10A	1.0296	0.8886	0.9821	0.054*
H10B	0.9483	0.9520	1.0459	0.054*
C11	0.8584 (3)	0.9420 (3)	0.93971 (18)	0.0394 (7)
H11A	0.8898	1.0162	0.9217	0.047*
H11B	0.7754	0.9545	0.9620	0.047*
C12	0.8463 (3)	0.8601 (2)	0.86874 (16)	0.0342 (7)
C13	0.8157 (3)	0.7368 (2)	0.89906 (15)	0.0315 (6)
H13A	0.7299	0.7428	0.9199	0.038*
C14	0.8065 (3)	0.6461 (3)	0.83505 (17)	0.0399 (7)
H14A	0.7647	0.6789	0.7897	0.048*
H14B	0.8905	0.6225	0.8194	0.048*
C15	0.7339 (4)	0.5422 (3)	0.86324 (19)	0.0516 (9)
H15A	0.6446	0.5572	0.8566	0.062*
H15B	0.7554	0.4766	0.8305	0.062*
C16	0.7576 (3)	0.5105 (3)	0.94744 (17)	0.0360 (7)
C17	0.6993 (3)	0.4097 (3)	0.97657 (19)	0.0422 (7)
H17A	0.6530	0.3638	0.9423	0.051*
C18	1.0309 (3)	0.6521 (3)	0.9484 (2)	0.0503 (9)
H18A	1.0721	0.6245	0.9948	0.076*
H18B	1.0764	0.7172	0.9279	0.076*
H18C	1.0290	0.5916	0.9098	0.076*
C19	0.9654 (3)	0.8588 (3)	0.8168 (2)	0.0470 (8)
H19A	0.9961	0.7810	0.8121	0.071*
H19B	1.0293	0.9065	0.8402	0.071*
H19C	0.9450	0.8882	0.7657	0.071*
C20	0.7282 (3)	0.9018 (3)	0.82255 (18)	0.0374 (7)
C21	0.8260 (3)	1.0905 (3)	0.7773 (2)	0.0471 (8)
H21A	0.8521	1.1040	0.7236	0.057*
H21B	0.8994	1.0659	0.8069	0.057*
C22	0.7745 (3)	1.2020 (3)	0.8121 (2)	0.0547 (9)
H22A	0.7576	1.1907	0.8674	0.066*
H22B	0.8372	1.2626	0.8071	0.066*
C23	0.6547 (4)	1.2390 (3)	0.7712 (2)	0.0635 (11)
H23A	0.6193	1.3057	0.7978	0.076*
H23B	0.6737	1.2612	0.7177	0.076*
C24	0.5606 (3)	1.1423 (3)	0.7712 (2)	0.0590 (10)
H24A	0.4873	1.1648	0.7409	0.071*
H24B	0.5335	1.1269	0.8244	0.071*
C25	0.6176 (4)	1.0337 (3)	0.7364 (2)	0.0557 (10)
H25A	0.5564	0.9715	0.7384	0.067*
H25B	0.6387	1.0474	0.6818	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0383 (12)	0.0497 (13)	0.0714 (15)	−0.0063 (11)	−0.0142 (11)	0.0160 (13)
N1	0.0447 (15)	0.0370 (13)	0.0505 (15)	−0.0036 (13)	−0.0108 (13)	0.0038 (13)
C1	0.088 (3)	0.050 (2)	0.106 (3)	−0.001 (2)	−0.003 (3)	0.029 (2)
C2	0.067 (3)	0.065 (3)	0.121 (4)	−0.021 (2)	−0.008 (3)	0.026 (3)
C3	0.066 (2)	0.0497 (19)	0.060 (2)	−0.006 (2)	0.009 (2)	0.0077 (18)
C4	0.0407 (17)	0.0417 (17)	0.0540 (18)	0.0018 (16)	0.0019 (16)	0.0101 (16)
C5	0.064 (2)	0.058 (2)	0.0425 (18)	−0.003 (2)	−0.0047 (18)	0.0130 (17)
C6	0.050 (2)	0.0485 (18)	0.0466 (18)	−0.0065 (17)	−0.0117 (16)	0.0032 (15)
C7	0.0294 (14)	0.0360 (16)	0.0431 (16)	0.0071 (13)	−0.0007 (13)	0.0017 (14)
C8	0.0269 (14)	0.0385 (16)	0.0398 (16)	0.0006 (13)	0.0003 (13)	0.0000 (14)
C9	0.0381 (16)	0.0468 (18)	0.0397 (16)	−0.0040 (15)	−0.0073 (14)	−0.0008 (15)
C10	0.0404 (17)	0.0468 (19)	0.0477 (19)	−0.0090 (16)	−0.0051 (14)	−0.0069 (16)
C11	0.0351 (15)	0.0358 (16)	0.0473 (17)	−0.0049 (14)	0.0016 (14)	0.0003 (14)
C12	0.0309 (15)	0.0362 (15)	0.0355 (15)	0.0002 (14)	0.0016 (12)	0.0005 (13)
C13	0.0268 (13)	0.0336 (14)	0.0340 (14)	−0.0010 (13)	0.0000 (12)	−0.0028 (12)
C14	0.0442 (17)	0.0371 (16)	0.0383 (15)	0.0017 (15)	0.0046 (14)	0.0002 (13)
C15	0.070 (2)	0.0382 (17)	0.0464 (17)	−0.0110 (18)	−0.0088 (17)	−0.0014 (15)
C16	0.0329 (14)	0.0341 (15)	0.0409 (15)	0.0065 (13)	0.0006 (13)	0.0006 (13)
C17	0.0388 (17)	0.0361 (16)	0.0517 (18)	0.0029 (15)	−0.0046 (15)	0.0004 (14)
C18	0.0271 (15)	0.057 (2)	0.067 (2)	0.0074 (16)	−0.0019 (15)	0.0048 (19)
C19	0.0370 (16)	0.0455 (18)	0.058 (2)	0.0024 (16)	0.0118 (15)	0.0059 (17)
C20	0.0398 (16)	0.0333 (15)	0.0392 (16)	−0.0008 (14)	−0.0012 (13)	−0.0039 (13)
C21	0.0485 (19)	0.0438 (18)	0.0490 (18)	−0.0056 (16)	0.0081 (16)	0.0087 (15)
C22	0.057 (2)	0.0395 (18)	0.067 (2)	−0.0076 (18)	−0.0050 (19)	−0.0012 (17)
C23	0.078 (3)	0.0381 (19)	0.074 (2)	0.007 (2)	−0.021 (2)	−0.0046 (18)
C24	0.051 (2)	0.057 (2)	0.069 (2)	0.009 (2)	−0.0193 (19)	0.002 (2)
C25	0.063 (2)	0.0461 (19)	0.058 (2)	−0.0042 (18)	−0.0235 (19)	0.0049 (18)

Geometric parameters (Å, º)

O1—C20	1.226 (4)	C12—C19	1.544 (4)
N1—C20	1.354 (4)	C12—C13	1.552 (4)
N1—C21	1.457 (4)	C12—C20	1.557 (4)
N1—C25	1.461 (4)	C13—C14	1.517 (4)
C1—C3	1.517 (6)	C13—H13A	0.9800
C1—H1A	0.9600	C14—C15	1.507 (4)
C1—H1B	0.9600	C14—H14A	0.9700
C1—H1C	0.9600	C14—H14B	0.9700
C2—C3	1.505 (6)	C15—C16	1.504 (4)
C2—H2A	0.9600	C15—H15A	0.9700
C2—H2B	0.9600	C15—H15B	0.9700
C2—H2C	0.9600	C16—C17	1.410 (4)
C3—C4	1.518 (5)	C17—H17A	0.9300
C3—H3	0.9800	C18—H18A	0.9600
C4—C5	1.375 (5)	C18—H18B	0.9600
C4—C17	1.382 (4)	C18—H18C	0.9600
C5—C6	1.378 (5)	C19—H19A	0.9600
C5—H5	0.9300	C19—H19B	0.9600
C6—C7	1.397 (4)	C19—H19C	0.9600
C6—H6	0.9300	C21—C22	1.521 (5)
C7—C16	1.391 (4)	C21—H21A	0.9700
C7—C8	1.535 (4)	C21—H21B	0.9700
C8—C9	1.544 (4)	C22—C23	1.511 (5)
C8—C18	1.546 (4)	C22—H22A	0.9700
C8—C13	1.554 (4)	C22—H22B	0.9700
C9—C10	1.514 (4)	C23—C24	1.500 (5)
C9—H9A	0.9700	C23—H23A	0.9700
C9—H9B	0.9700	C23—H23B	0.9700
C10—C11	1.514 (4)	C24—C25	1.514 (5)
C10—H10A	0.9700	C24—H24A	0.9700
C10—H10B	0.9700	C24—H24B	0.9700
C11—C12	1.543 (4)	C25—H25A	0.9700
C11—H11A	0.9700	C25—H25B	0.9700
C11—H11B	0.9700
C20—N1—C21	129.0 (3)	C14—C13—H13A	104.5
C20—N1—C25	118.8 (3)	C12—C13—H13A	104.5
C21—N1—C25	111.5 (3)	C8—C13—H13A	104.5
C3—C1—H1A	109.5	C15—C14—C13	110.7 (2)
C3—C1—H1B	109.5	C15—C14—H14A	109.5
H1A—C1—H1B	109.5	C13—C14—H14A	109.5
C3—C1—H1C	109.5	C15—C14—H14B	109.5
H1A—C1—H1C	109.5	C13—C14—H14B	109.5
H1B—C1—H1C	109.5	H14A—C14—H14B	108.1
C3—C2—H2A	109.5	C16—C15—C14	114.4 (3)
C3—C2—H2B	109.5	C16—C15—H15A	108.6
H2A—C2—H2B	109.5	C14—C15—H15A	108.6
C3—C2—H2C	109.5	C16—C15—H15B	108.6
H2A—C2—H2C	109.5	C14—C15—H15B	108.6
H2B—C2—H2C	109.5	H15A—C15—H15B	107.6
C2—C3—C1	110.4 (3)	C7—C16—C17	119.5 (3)
C2—C3—C4	114.5 (3)	C7—C16—C15	122.7 (3)
C1—C3—C4	110.8 (3)	C17—C16—C15	117.7 (3)
C2—C3—H3	106.9	C4—C17—C16	122.4 (3)
C1—C3—H3	106.9	C4—C17—H17A	118.8
C4—C3—H3	106.9	C16—C17—H17A	118.8
C5—C4—C17	117.1 (3)	C8—C18—H18A	109.5
C5—C4—C3	119.7 (3)	C8—C18—H18B	109.5
C17—C4—C3	123.2 (3)	H18A—C18—H18B	109.5
C4—C5—C6	121.9 (3)	C8—C18—H18C	109.5
C4—C5—H5	119.1	H18A—C18—H18C	109.5
C6—C5—H5	119.1	H18B—C18—H18C	109.5
C5—C6—C7	121.5 (3)	C12—C19—H19A	109.5
C5—C6—H6	119.2	C12—C19—H19B	109.5
C7—C6—H6	119.2	H19A—C19—H19B	109.5
C16—C7—C6	117.6 (3)	C12—C19—H19C	109.5
C16—C7—C8	121.4 (3)	H19A—C19—H19C	109.5
C6—C7—C8	121.0 (3)	H19B—C19—H19C	109.5
C7—C8—C9	110.6 (2)	O1—C20—N1	118.9 (3)
C7—C8—C18	106.1 (2)	O1—C20—C12	119.8 (3)
C9—C8—C18	108.4 (3)	N1—C20—C12	121.3 (3)
C7—C8—C13	106.9 (2)	N1—C21—C22	110.7 (3)
C9—C8—C13	109.1 (2)	N1—C21—H21A	109.5
C18—C8—C13	115.7 (3)	C22—C21—H21A	109.5
C10—C9—C8	111.8 (2)	N1—C21—H21B	109.5
C10—C9—H9A	109.3	C22—C21—H21B	109.5
C8—C9—H9A	109.3	H21A—C21—H21B	108.1
C10—C9—H9B	109.3	C23—C22—C21	111.3 (3)
C8—C9—H9B	109.3	C23—C22—H22A	109.4
H9A—C9—H9B	107.9	C21—C22—H22A	109.4
C9—C10—C11	111.3 (3)	C23—C22—H22B	109.4
C9—C10—H10A	109.4	C21—C22—H22B	109.4
C11—C10—H10A	109.4	H22A—C22—H22B	108.0
C9—C10—H10B	109.4	C24—C23—C22	110.4 (3)
C11—C10—H10B	109.4	C24—C23—H23A	109.6
H10A—C10—H10B	108.0	C22—C23—H23A	109.6
C10—C11—C12	113.5 (3)	C24—C23—H23B	109.6
C10—C11—H11A	108.9	C22—C23—H23B	109.6
C12—C11—H11A	108.9	H23A—C23—H23B	108.1
C10—C11—H11B	108.9	C23—C24—C25	110.7 (3)
C12—C11—H11B	108.9	C23—C24—H24A	109.5
H11A—C11—H11B	107.7	C25—C24—H24A	109.5
C11—C12—C19	112.9 (3)	C23—C24—H24B	109.5
C11—C12—C13	108.7 (2)	C25—C24—H24B	109.5
C19—C12—C13	110.8 (2)	H24A—C24—H24B	108.1
C11—C12—C20	105.9 (2)	N1—C25—C24	110.8 (3)
C19—C12—C20	111.8 (2)	N1—C25—H25A	109.5
C13—C12—C20	106.6 (2)	C24—C25—H25A	109.5
C14—C13—C12	114.1 (2)	N1—C25—H25B	109.5
C14—C13—C8	109.8 (2)	C24—C25—H25B	109.5
C12—C13—C8	117.9 (2)	H25A—C25—H25B	108.1
C2—C3—C4—C5	161.6 (4)	C9—C8—C13—C12	48.4 (3)
C1—C3—C4—C5	−72.8 (4)	C18—C8—C13—C12	−74.0 (3)
C2—C3—C4—C17	−19.8 (5)	C12—C13—C14—C15	−160.0 (3)
C1—C3—C4—C17	105.8 (4)	C8—C13—C14—C15	65.1 (3)
C17—C4—C5—C6	0.7 (5)	C13—C14—C15—C16	−37.4 (4)
C3—C4—C5—C6	179.4 (3)	C6—C7—C16—C17	1.4 (4)
C4—C5—C6—C7	1.1 (5)	C8—C7—C16—C17	179.0 (2)
C5—C6—C7—C16	−2.1 (5)	C6—C7—C16—C15	177.4 (3)
C5—C6—C7—C8	−179.7 (3)	C8—C7—C16—C15	−4.9 (5)
C16—C7—C8—C9	148.5 (3)	C14—C15—C16—C7	7.9 (5)
C6—C7—C8—C9	−34.0 (4)	C14—C15—C16—C17	−176.0 (3)
C16—C7—C8—C18	−94.2 (3)	C5—C4—C17—C16	−1.4 (5)
C6—C7—C8—C18	83.4 (3)	C3—C4—C17—C16	180.0 (3)
C16—C7—C8—C13	29.9 (4)	C7—C16—C17—C4	0.3 (5)
C6—C7—C8—C13	−152.6 (3)	C15—C16—C17—C4	−175.9 (3)
C7—C8—C9—C10	−170.1 (2)	C21—N1—C20—O1	167.1 (3)
C18—C8—C9—C10	73.9 (3)	C25—N1—C20—O1	−2.1 (4)
C13—C8—C9—C10	−52.8 (3)	C21—N1—C20—C12	−11.6 (5)
C8—C9—C10—C11	59.8 (3)	C25—N1—C20—C12	179.3 (3)
C9—C10—C11—C12	−58.9 (3)	C11—C12—C20—O1	−104.9 (3)
C10—C11—C12—C19	−73.1 (3)	C19—C12—C20—O1	131.8 (3)
C10—C11—C12—C13	50.1 (3)	C13—C12—C20—O1	10.7 (4)
C10—C11—C12—C20	164.3 (2)	C11—C12—C20—N1	73.8 (3)
C11—C12—C13—C14	−177.6 (2)	C19—C12—C20—N1	−49.5 (4)
C19—C12—C13—C14	−53.1 (3)	C13—C12—C20—N1	−170.6 (2)
C20—C12—C13—C14	68.7 (3)	C20—N1—C21—C22	−111.6 (4)
C11—C12—C13—C8	−46.6 (3)	C25—N1—C21—C22	58.3 (4)
C19—C12—C13—C8	77.9 (3)	N1—C21—C22—C23	−55.3 (4)
C20—C12—C13—C8	−160.3 (2)	C21—C22—C23—C24	53.5 (4)
C7—C8—C13—C14	−59.0 (3)	C22—C23—C24—C25	−54.2 (4)
C9—C8—C13—C14	−178.6 (2)	C20—N1—C25—C24	111.5 (3)
C18—C8—C13—C14	58.9 (3)	C21—N1—C25—C24	−59.5 (4)
C7—C8—C13—C12	168.0 (2)	C23—C24—C25—N1	57.3 (4)