16-(2-Pyridyl­methyl­ene)­androst-4-ene-3,17-dione

The title compound, C₂₅H₂₉NO₂, crystallizes in the triclinic space group P1 with two crystallographically independent mol­ecules in the unit cell. These two mol­ecules differ in the orientation of the pyridyl rings with respect to the steroid nucleus, and also in the conformation of the five-membered rings.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.102
• Data-to-parameter ratio = 8.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           67.99
         From the CIF: _reflns_number_total               4136
         Count of symmetry unique reflns         3800
         Completeness (_total/calc)            108.84%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured       336
         Fraction of Friedel pairs measured     0.088
         Are heavy atom types Z>Si present           no
          WARNING: CuKa measured Friedel data can be used to
                   determine absolute structure in a light-atom
                   study only if the Friedel fraction is large.

---

Computing details

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEP97 (Zsolnai, 1997); software used to prepare material for publication: SHELXL97.

16-(2-Pyridylmethylene)-androst-4-ene-3,17-dione

Crystal data

C25H29NO2	Z = 2
Mr = 375.49	F(000) = 404
Triclinic, P1	Dx = 1.197 Mg m^−3
a = 6.991 (1) Å	Cu Kα radiation, λ = 1.5418 Å
b = 11.674 (2) Å	Cell parameters from 25 reflections
c = 13.528 (2) Å	θ = 20–30°
α = 79.327 (10)°	µ = 0.59 mm^−1
β = 76.866 (13)°	T = 293 K
γ = 78.438 (14)°	Plate, white
V = 1042.0 (3) Å^3	0.5 × 0.4 × 0.15 mm

Data collection

Enraf-Nonius CAD-4 diffractometer	3938 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
Graphite monochromator	θmax = 68.0°, θmin = 3.4°
ω–2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −13→14
Tmin = 0.759, Tmax = 0.917	l = −15→16
4136 measured reflections	2 standard reflections every 120 min
4136 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.036	w = 1/[σ^2(Fo^2) + (0.0837P)^2 + 0.0801P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max < 0.001
S = 0.93	Δρmax = 0.21 e Å^−3
4136 reflections	Δρmin = −0.15 e Å^−3
506 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.0121 (11)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.0 (2)

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
C1	−0.3953 (3)	0.0123 (2)	0.12988 (18)	0.0559 (5)
H1A	−0.4166	0.0948	0.1387	0.067*
H1B	−0.4484	0.0080	0.0706	0.067*
C2	−0.5087 (4)	−0.0555 (2)	0.2240 (2)	0.0655 (6)
H2A	−0.4664	−0.0445	0.2847	0.079*
H2B	−0.6500	−0.0248	0.2312	0.079*
C3	−0.4736 (4)	−0.1842 (3)	0.2162 (2)	0.0662 (6)
C4	−0.2779 (4)	−0.2327 (2)	0.16306 (18)	0.0613 (6)
H4	−0.2506	−0.3134	0.1600	0.074*
C5	−0.1339 (3)	−0.16857 (18)	0.11803 (15)	0.0505 (5)
C6	0.0741 (4)	−0.2268 (2)	0.08000 (18)	0.0615 (6)
H6A	0.0735	−0.3093	0.0777	0.074*
H6B	0.1561	−0.2240	0.1282	0.074*
C7	0.1676 (4)	−0.1692 (2)	−0.02660 (19)	0.0671 (7)
H7A	0.3078	−0.2026	−0.0422	0.080*
H7B	0.1040	−0.1869	−0.0774	0.080*
C8	0.1459 (3)	−0.03586 (18)	−0.03330 (15)	0.0477 (4)
H8	0.2196	−0.0183	0.0141	0.057*
C9	−0.0763 (3)	0.01709 (18)	−0.00250 (15)	0.0462 (4)
H9	−0.1453	−0.0084	−0.0480	0.055*
C10	−0.1702 (3)	−0.03432 (18)	0.10890 (14)	0.0443 (4)
C11	−0.1158 (3)	0.15282 (19)	−0.02141 (17)	0.0550 (5)
H11A	−0.0621	0.1821	0.0274	0.066*
H11B	−0.2585	0.1800	−0.0091	0.066*
C12	−0.0238 (4)	0.2053 (2)	−0.13073 (18)	0.0573 (5)
H12A	−0.0884	0.1849	−0.1799	0.069*
H12B	−0.0434	0.2907	−0.1367	0.069*
C13	0.1977 (3)	0.15619 (18)	−0.15334 (15)	0.0501 (5)
C14	0.2271 (3)	0.02097 (18)	−0.14185 (15)	0.0501 (5)
H14	0.1475	0.0027	−0.1861	0.060*
C15	0.4467 (4)	−0.0156 (2)	−0.19231 (18)	0.0615 (6)
H15A	0.5354	−0.0164	−0.1464	0.074*
H15B	0.4694	−0.0925	−0.2143	0.074*
C16	0.4717 (4)	0.0822 (2)	−0.28326 (18)	0.0583 (5)
C17	0.3086 (4)	0.1844 (2)	−0.26262 (16)	0.0553 (5)
C18	0.3110 (4)	0.2021 (2)	−0.08811 (18)	0.0633 (6)
H18A	0.2483	0.1878	−0.0171	0.095*
H18B	0.3092	0.2854	−0.1091	0.095*
H18C	0.4463	0.1617	−0.0974	0.095*
C19	−0.0752 (3)	−0.0017 (2)	0.18985 (16)	0.0551 (5)
H19A	−0.0960	0.0828	0.1859	0.083*
H19B	0.0651	−0.0315	0.1771	0.083*
H19C	−0.1356	−0.0358	0.2570	0.083*
C20	0.6039 (4)	0.0851 (2)	−0.37216 (18)	0.0602 (5)
H20	0.5811	0.1507	−0.4214	0.072*
C21	0.7795 (4)	−0.0023 (2)	−0.40099 (18)	0.0590 (5)
C22	0.8601 (4)	−0.0086 (2)	−0.50445 (18)	0.0624 (6)
H22	0.8006	0.0416	−0.5549	0.075*
C23	1.0275 (4)	−0.0892 (3)	−0.5313 (2)	0.0708 (7)
H23	1.0822	−0.0958	−0.5998	0.085*
C24	1.1115 (5)	−0.1593 (3)	−0.4547 (3)	0.0851 (9)
H24	1.2253	−0.2149	−0.4699	0.102*
C25	1.0247 (6)	−0.1465 (4)	−0.3539 (3)	0.0978 (11)
H25	1.0849	−0.1942	−0.3025	0.117*
N26	0.8621 (4)	−0.0711 (3)	−0.32599 (18)	0.0863 (8)
O27	0.2751 (3)	0.27511 (15)	−0.32077 (13)	0.0707 (5)
O28	−0.6009 (3)	−0.2460 (2)	0.2577 (2)	0.0987 (7)
C1A	−0.3115 (4)	0.4305 (2)	0.66216 (17)	0.0601 (6)
H1A1	−0.3246	0.3480	0.6706	0.072*
H1A2	−0.1948	0.4346	0.6880	0.072*
C2A	−0.4935 (5)	0.4959 (3)	0.7254 (2)	0.0719 (7)
H2A1	−0.6118	0.4782	0.7093	0.086*
H2A2	−0.4947	0.4672	0.7975	0.086*
C3A	−0.5020 (4)	0.6260 (2)	0.70748 (19)	0.0634 (6)
C4A	−0.3929 (4)	0.6772 (2)	0.60877 (19)	0.0612 (6)
H4A	−0.3874	0.7576	0.5982	0.073*
C5A	−0.3004 (3)	0.61426 (19)	0.53286 (17)	0.0496 (4)
C6A	−0.2272 (4)	0.67549 (19)	0.42688 (18)	0.0577 (5)
H6A1	−0.2264	0.7576	0.4305	0.069*
H6A2	−0.3193	0.6739	0.3835	0.069*
C7A	−0.0200 (3)	0.61984 (18)	0.37796 (18)	0.0540 (5)
H7A1	0.0765	0.6339	0.4139	0.065*
H7A2	0.0121	0.6567	0.3072	0.065*
C8A	−0.0054 (3)	0.48679 (17)	0.38133 (15)	0.0432 (4)
H8A	−0.0953	0.4727	0.3405	0.052*
C9A	−0.0660 (3)	0.42827 (17)	0.49386 (15)	0.0434 (4)
H9A	0.0250	0.4472	0.5316	0.052*
C10A	−0.2795 (3)	0.48053 (18)	0.54663 (15)	0.0458 (4)
C11A	−0.0317 (3)	0.29265 (19)	0.50398 (18)	0.0547 (5)
H11C	−0.0620	0.2601	0.5760	0.066*
H11D	−0.1228	0.2695	0.4699	0.066*
C12A	0.1812 (3)	0.24017 (19)	0.45812 (17)	0.0541 (5)
H12C	0.2722	0.2547	0.4972	0.065*
H12D	0.1921	0.1554	0.4621	0.065*
C13A	0.2376 (3)	0.29510 (17)	0.34706 (15)	0.0468 (4)
C14A	0.2063 (3)	0.43025 (17)	0.33946 (15)	0.0428 (4)
H14A	0.2871	0.4454	0.3846	0.051*
C15A	0.3142 (3)	0.47153 (19)	0.22942 (16)	0.0504 (5)
H15C	0.2335	0.4733	0.1794	0.061*
H15D	0.3501	0.5489	0.2235	0.061*
C16A	0.4963 (3)	0.37660 (19)	0.21744 (16)	0.0504 (5)
C17A	0.4565 (3)	0.27260 (19)	0.29900 (17)	0.0507 (5)
C18A	0.1263 (4)	0.2524 (2)	0.2784 (2)	0.0626 (6)
H18D	−0.0140	0.2645	0.3066	0.094*
H18E	0.1732	0.1698	0.2750	0.094*
H18F	0.1502	0.2963	0.2106	0.094*
C19A	−0.4390 (3)	0.4515 (2)	0.4977 (2)	0.0592 (5)
H19D	−0.4299	0.3673	0.5049	0.089*
H19E	−0.4180	0.4838	0.4262	0.089*
H19F	−0.5687	0.4853	0.5314	0.089*
C20A	0.6744 (3)	0.3732 (2)	0.15470 (17)	0.0551 (5)
H20A	0.7661	0.3054	0.1679	0.066*
C21A	0.7478 (4)	0.4599 (2)	0.06827 (17)	0.0565 (5)
C22A	0.6266 (4)	0.5459 (3)	0.0164 (2)	0.0713 (7)
H22A	0.4889	0.5541	0.0371	0.086*
C23A	0.7118 (6)	0.6206 (3)	−0.0672 (2)	0.0848 (9)
H23A	0.6326	0.6794	−0.1034	0.102*
C24A	0.9160 (6)	0.6054 (3)	−0.0952 (2)	0.0872 (9)
H24A	0.9782	0.6534	−0.1510	0.105*
C25A	1.0247 (5)	0.5185 (3)	−0.0391 (3)	0.0854 (9)
H25A	1.1627	0.5096	−0.0580	0.102*
N26A	0.9476 (3)	0.4453 (2)	0.04085 (19)	0.0737 (6)
O27A	0.5789 (3)	0.18836 (16)	0.32203 (15)	0.0707 (5)
O28A	−0.6019 (4)	0.6883 (2)	0.77027 (17)	0.0900 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0416 (11)	0.0619 (12)	0.0592 (13)	−0.0071 (9)	−0.0068 (9)	−0.0019 (10)
C2	0.0411 (11)	0.0799 (16)	0.0688 (14)	−0.0151 (11)	−0.0001 (10)	−0.0017 (12)
C3	0.0546 (13)	0.0824 (16)	0.0640 (13)	−0.0281 (12)	−0.0129 (11)	0.0032 (12)
C4	0.0692 (15)	0.0603 (12)	0.0550 (12)	−0.0226 (11)	−0.0068 (11)	−0.0033 (10)
C5	0.0564 (12)	0.0533 (11)	0.0401 (9)	−0.0096 (9)	−0.0077 (9)	−0.0045 (8)
C6	0.0653 (14)	0.0498 (11)	0.0533 (12)	−0.0016 (10)	0.0070 (10)	0.0008 (9)
C7	0.0769 (16)	0.0500 (11)	0.0544 (12)	−0.0001 (11)	0.0154 (12)	−0.0036 (9)
C8	0.0467 (11)	0.0497 (10)	0.0390 (9)	−0.0033 (9)	0.0004 (8)	−0.0031 (8)
C9	0.0471 (11)	0.0482 (10)	0.0405 (9)	−0.0055 (8)	−0.0065 (8)	−0.0044 (8)
C10	0.0401 (9)	0.0511 (10)	0.0389 (9)	−0.0062 (8)	−0.0052 (8)	−0.0044 (8)
C11	0.0503 (11)	0.0499 (11)	0.0543 (12)	−0.0011 (9)	0.0000 (9)	−0.0014 (9)
C12	0.0575 (13)	0.0516 (11)	0.0541 (12)	−0.0028 (10)	−0.0073 (10)	0.0029 (9)
C13	0.0521 (12)	0.0503 (11)	0.0426 (10)	−0.0094 (9)	−0.0031 (9)	0.0002 (8)
C14	0.0541 (12)	0.0484 (10)	0.0412 (10)	−0.0080 (9)	−0.0002 (9)	−0.0024 (8)
C15	0.0629 (14)	0.0579 (12)	0.0486 (11)	−0.0046 (11)	0.0093 (10)	−0.0008 (9)
C16	0.0606 (13)	0.0578 (12)	0.0488 (11)	−0.0120 (10)	0.0019 (10)	−0.0015 (9)
C17	0.0613 (13)	0.0562 (11)	0.0452 (11)	−0.0161 (10)	−0.0045 (10)	0.0001 (9)
C18	0.0676 (14)	0.0664 (13)	0.0560 (12)	−0.0178 (12)	−0.0072 (11)	−0.0080 (10)
C19	0.0496 (12)	0.0715 (13)	0.0453 (10)	−0.0102 (10)	−0.0075 (9)	−0.0131 (9)
C20	0.0623 (13)	0.0624 (12)	0.0481 (11)	−0.0155 (11)	0.0009 (10)	0.0025 (9)
C21	0.0568 (13)	0.0646 (13)	0.0486 (11)	−0.0160 (11)	0.0018 (10)	0.0003 (9)
C22	0.0640 (14)	0.0680 (13)	0.0487 (12)	−0.0155 (11)	0.0014 (10)	−0.0026 (10)
C23	0.0676 (15)	0.0788 (16)	0.0594 (13)	−0.0162 (13)	0.0058 (12)	−0.0116 (12)
C24	0.0608 (16)	0.093 (2)	0.0847 (19)	0.0014 (15)	0.0031 (14)	−0.0081 (16)
C25	0.079 (2)	0.114 (2)	0.0739 (17)	0.0135 (19)	−0.0063 (16)	0.0098 (17)
N26	0.0725 (15)	0.1081 (19)	0.0572 (12)	0.0021 (14)	−0.0008 (11)	0.0076 (12)
O27	0.0828 (12)	0.0626 (10)	0.0537 (8)	−0.0110 (9)	−0.0019 (8)	0.0090 (7)
O28	0.0737 (14)	0.1023 (16)	0.1201 (18)	−0.0530 (13)	−0.0021 (13)	0.0047 (14)
C1A	0.0614 (14)	0.0651 (13)	0.0454 (11)	−0.0108 (11)	0.0029 (10)	−0.0031 (9)
C2A	0.0701 (16)	0.0831 (17)	0.0544 (12)	−0.0163 (14)	0.0106 (12)	−0.0144 (12)
C3A	0.0537 (13)	0.0801 (15)	0.0556 (12)	−0.0057 (12)	−0.0029 (10)	−0.0233 (12)
C4A	0.0541 (12)	0.0610 (12)	0.0660 (14)	−0.0091 (10)	−0.0002 (10)	−0.0179 (10)
C5A	0.0367 (9)	0.0560 (11)	0.0536 (11)	−0.0082 (8)	−0.0039 (8)	−0.0072 (9)
C6A	0.0519 (12)	0.0477 (10)	0.0615 (13)	−0.0035 (9)	0.0028 (10)	−0.0003 (9)
C7A	0.0462 (11)	0.0478 (11)	0.0571 (11)	−0.0073 (9)	0.0057 (9)	−0.0004 (9)
C8A	0.0369 (9)	0.0466 (10)	0.0446 (9)	−0.0096 (8)	−0.0037 (7)	−0.0050 (8)
C9A	0.0373 (9)	0.0488 (10)	0.0431 (9)	−0.0119 (8)	−0.0044 (7)	−0.0035 (7)
C10A	0.0389 (10)	0.0527 (11)	0.0444 (10)	−0.0123 (8)	−0.0024 (8)	−0.0055 (8)
C11A	0.0534 (12)	0.0484 (11)	0.0558 (11)	−0.0142 (9)	0.0011 (10)	0.0003 (9)
C12A	0.0541 (12)	0.0460 (10)	0.0557 (11)	−0.0053 (9)	−0.0046 (10)	−0.0021 (8)
C13A	0.0422 (10)	0.0467 (10)	0.0497 (11)	−0.0084 (8)	−0.0037 (8)	−0.0085 (8)
C14A	0.0362 (9)	0.0463 (10)	0.0442 (9)	−0.0087 (8)	−0.0038 (8)	−0.0050 (7)
C15A	0.0419 (10)	0.0530 (11)	0.0496 (10)	−0.0080 (9)	0.0015 (8)	−0.0032 (8)
C16A	0.0432 (10)	0.0554 (11)	0.0496 (10)	−0.0054 (9)	−0.0027 (8)	−0.0108 (8)
C17A	0.0446 (10)	0.0538 (11)	0.0511 (10)	−0.0025 (9)	−0.0047 (9)	−0.0127 (8)
C18A	0.0607 (13)	0.0646 (13)	0.0684 (14)	−0.0160 (11)	−0.0125 (11)	−0.0186 (11)
C19A	0.0395 (10)	0.0724 (14)	0.0681 (13)	−0.0183 (10)	−0.0046 (9)	−0.0135 (11)
C20A	0.0439 (11)	0.0627 (12)	0.0536 (11)	−0.0036 (9)	−0.0004 (9)	−0.0129 (9)
C21A	0.0493 (11)	0.0644 (12)	0.0518 (11)	−0.0094 (10)	0.0046 (9)	−0.0167 (9)
C22A	0.0612 (14)	0.0884 (18)	0.0561 (13)	−0.0074 (13)	−0.0014 (11)	−0.0078 (12)
C23A	0.098 (2)	0.0861 (19)	0.0607 (14)	−0.0116 (17)	−0.0073 (15)	−0.0009 (13)
C24A	0.097 (2)	0.093 (2)	0.0639 (16)	−0.0359 (18)	0.0148 (16)	−0.0078 (15)
C25A	0.0669 (17)	0.099 (2)	0.0827 (19)	−0.0264 (16)	0.0146 (15)	−0.0172 (17)
N26A	0.0486 (11)	0.0846 (14)	0.0774 (14)	−0.0115 (10)	0.0115 (10)	−0.0145 (11)
O27A	0.0563 (10)	0.0647 (9)	0.0738 (11)	0.0098 (8)	−0.0018 (8)	−0.0017 (8)
O28A	0.0842 (13)	0.1013 (14)	0.0745 (12)	0.0010 (12)	0.0101 (11)	−0.0373 (11)

Geometric parameters (Å, º)

C1—C2	1.516 (3)	C1A—C2A	1.513 (3)
C1—C10	1.538 (3)	C1A—C10A	1.546 (3)
C1—H1A	0.97	C1A—H1A1	0.97
C1—H1B	0.97	C1A—H1A2	0.97
C2—C3	1.492 (4)	C2A—C3A	1.485 (4)
C2—H2A	0.97	C2A—H2A1	0.97
C2—H2B	0.97	C2A—H2A2	0.97
C3—O28	1.228 (3)	C3A—O28A	1.222 (3)
C3—C4	1.450 (4)	C3A—C4A	1.465 (4)
C4—C5	1.342 (3)	C4A—C5A	1.341 (3)
C4—H4	0.93	C4A—H4A	0.93
C5—C6	1.495 (3)	C5A—C6A	1.504 (3)
C5—C10	1.523 (3)	C5A—C10A	1.519 (3)
C6—C7	1.532 (3)	C6A—C7A	1.518 (3)
C6—H6A	0.97	C6A—H6A1	0.97
C6—H6B	0.97	C6A—H6A2	0.97
C7—C8	1.521 (3)	C7A—C8A	1.529 (3)
C7—H7A	0.97	C7A—H7A1	0.97
C7—H7B	0.97	C7A—H7A2	0.97
C8—C14	1.526 (3)	C8A—C14A	1.521 (3)
C8—C9	1.545 (3)	C8A—C9A	1.550 (2)
C8—H8	0.98	C8A—H8A	0.98
C9—C11	1.536 (3)	C9A—C11A	1.538 (3)
C9—C10	1.560 (3)	C9A—C10A	1.556 (3)
C9—H9	0.98	C9A—H9A	0.98
C10—C19	1.540 (3)	C10A—C19A	1.539 (3)
C11—C12	1.538 (3)	C11A—C12A	1.527 (3)
C11—H11A	0.97	C11A—H11C	0.97
C11—H11B	0.97	C11A—H11D	0.97
C12—C13	1.521 (3)	C12A—C13A	1.516 (3)
C12—H12A	0.97	C12A—H12C	0.97
C12—H12B	0.97	C12A—H12D	0.97
C13—C17	1.515 (3)	C13A—C17A	1.511 (3)
C13—C14	1.534 (3)	C13A—C14A	1.536 (3)
C13—C18	1.535 (3)	C13A—C18A	1.541 (3)
C14—C15	1.541 (3)	C14A—C15A	1.545 (3)
C14—H14	0.98	C14A—H14A	0.98
C15—C16	1.519 (3)	C15A—C16A	1.510 (3)
C15—H15A	0.97	C15A—H15C	0.97
C15—H15B	0.97	C15A—H15D	0.97
C16—C20	1.340 (3)	C16A—C20A	1.336 (3)
C16—C17	1.495 (3)	C16A—C17A	1.506 (3)
C17—O27	1.212 (3)	C17A—O27A	1.211 (3)
C18—H18A	0.96	C18A—H18D	0.96
C18—H18B	0.96	C18A—H18E	0.96
C18—H18C	0.96	C18A—H18F	0.96
C19—H19A	0.96	C19A—H19D	0.96
C19—H19B	0.96	C19A—H19E	0.96
C19—H19C	0.96	C19A—H19F	0.96
C20—C21	1.459 (4)	C20A—C21A	1.467 (3)
C20—H20	0.93	C20A—H20A	0.93
C21—N26	1.337 (3)	C21A—N26A	1.346 (3)
C21—C22	1.395 (3)	C21A—C22A	1.373 (4)
C22—C23	1.370 (4)	C22A—C23A	1.390 (4)
C22—H22	0.93	C22A—H22A	0.93
C23—C24	1.364 (5)	C23A—C24A	1.375 (5)
C23—H23	0.93	C23A—H23A	0.93
C24—C25	1.383 (5)	C24A—C25A	1.360 (5)
C24—H24	0.93	C24A—H24A	0.93
C25—N26	1.318 (4)	C25A—N26A	1.329 (4)
C25—H25	0.93	C25A—H25A	0.93
C2—C1—C10	113.28 (18)	C2A—C1A—C10A	113.3 (2)
C2—C1—H1A	108.9	C2A—C1A—H1A1	108.9
C10—C1—H1A	108.9	C10A—C1A—H1A1	108.9
C2—C1—H1B	108.9	C2A—C1A—H1A2	108.9
C10—C1—H1B	108.9	C10A—C1A—H1A2	108.9
H1A—C1—H1B	107.7	H1A1—C1A—H1A2	107.7
C3—C2—C1	111.0 (2)	C3A—C2A—C1A	113.5 (2)
C3—C2—H2A	109.4	C3A—C2A—H2A1	108.9
C1—C2—H2A	109.4	C1A—C2A—H2A1	108.9
C3—C2—H2B	109.4	C3A—C2A—H2A2	108.9
C1—C2—H2B	109.4	C1A—C2A—H2A2	108.9
H2A—C2—H2B	108.0	H2A1—C2A—H2A2	107.7
O28—C3—C4	122.3 (3)	O28A—C3A—C4A	121.4 (3)
O28—C3—C2	121.2 (3)	O28A—C3A—C2A	121.7 (3)
C4—C3—C2	116.4 (2)	C4A—C3A—C2A	116.87 (19)
C5—C4—C3	124.1 (2)	C5A—C4A—C3A	123.5 (2)
C5—C4—H4	117.9	C5A—C4A—H4A	118.2
C3—C4—H4	117.9	C3A—C4A—H4A	118.2
C4—C5—C6	121.1 (2)	C4A—C5A—C6A	120.5 (2)
C4—C5—C10	122.0 (2)	C4A—C5A—C10A	122.4 (2)
C6—C5—C10	116.75 (19)	C6A—C5A—C10A	116.92 (18)
C5—C6—C7	113.31 (19)	C5A—C6A—C7A	113.30 (18)
C5—C6—H6A	108.9	C5A—C6A—H6A1	108.9
C7—C6—H6A	108.9	C7A—C6A—H6A1	108.9
C5—C6—H6B	108.9	C5A—C6A—H6A2	108.9
C7—C6—H6B	108.9	C7A—C6A—H6A2	108.9
H6A—C6—H6B	107.7	H6A1—C6A—H6A2	107.7
C8—C7—C6	111.95 (18)	C6A—C7A—C8A	111.40 (18)
C8—C7—H7A	109.2	C6A—C7A—H7A1	109.3
C6—C7—H7A	109.2	C8A—C7A—H7A1	109.3
C8—C7—H7B	109.2	C6A—C7A—H7A2	109.3
C6—C7—H7B	109.2	C8A—C7A—H7A2	109.3
H7A—C7—H7B	107.9	H7A1—C7A—H7A2	108.0
C7—C8—C14	111.24 (17)	C14A—C8A—C7A	111.07 (16)
C7—C8—C9	109.48 (19)	C14A—C8A—C9A	108.12 (15)
C14—C8—C9	108.92 (16)	C7A—C8A—C9A	109.55 (16)
C7—C8—H8	109.1	C14A—C8A—H8A	109.4
C14—C8—H8	109.1	C7A—C8A—H8A	109.4
C9—C8—H8	109.1	C9A—C8A—H8A	109.4
C11—C9—C8	113.12 (17)	C11A—C9A—C8A	112.09 (16)
C11—C9—C10	112.48 (16)	C11A—C9A—C10A	112.72 (16)
C8—C9—C10	112.29 (15)	C8A—C9A—C10A	113.24 (15)
C11—C9—H9	106.1	C11A—C9A—H9A	106.0
C8—C9—H9	106.1	C8A—C9A—H9A	106.0
C10—C9—H9	106.1	C10A—C9A—H9A	106.0
C5—C10—C1	109.82 (18)	C5A—C10A—C19A	107.21 (17)
C5—C10—C19	107.62 (17)	C5A—C10A—C1A	109.74 (17)
C1—C10—C19	109.54 (17)	C19A—C10A—C1A	110.46 (18)
C5—C10—C9	108.48 (15)	C5A—C10A—C9A	109.22 (15)
C1—C10—C9	109.23 (16)	C19A—C10A—C9A	111.41 (16)
C19—C10—C9	112.10 (17)	C1A—C10A—C9A	108.78 (17)
C9—C11—C12	113.28 (17)	C12A—C11A—C9A	113.03 (17)
C9—C11—H11A	108.9	C12A—C11A—H11C	109.0
C12—C11—H11A	108.9	C9A—C11A—H11C	109.0
C9—C11—H11B	108.9	C12A—C11A—H11D	109.0
C12—C11—H11B	108.9	C9A—C11A—H11D	109.0
H11A—C11—H11B	107.7	H11C—C11A—H11D	107.8
C13—C12—C11	109.25 (17)	C13A—C12A—C11A	110.26 (17)
C13—C12—H12A	109.8	C13A—C12A—H12C	109.6
C11—C12—H12A	109.8	C11A—C12A—H12C	109.6
C13—C12—H12B	109.8	C13A—C12A—H12D	109.6
C11—C12—H12B	109.8	C11A—C12A—H12D	109.6
H12A—C12—H12B	108.3	H12C—C12A—H12D	108.1
C17—C13—C12	116.87 (18)	C17A—C13A—C12A	115.95 (18)
C17—C13—C14	100.48 (16)	C17A—C13A—C14A	99.30 (16)
C12—C13—C14	109.39 (17)	C12A—C13A—C14A	109.85 (16)
C17—C13—C18	104.47 (18)	C17A—C13A—C18A	106.74 (17)
C12—C13—C18	111.53 (19)	C12A—C13A—C18A	111.12 (19)
C14—C13—C18	113.73 (18)	C14A—C13A—C18A	113.47 (17)
C8—C14—C13	112.91 (16)	C8A—C14A—C13A	114.52 (15)
C8—C14—C15	120.06 (18)	C8A—C14A—C15A	121.24 (16)
C13—C14—C15	104.44 (17)	C13A—C14A—C15A	104.10 (15)
C8—C14—H14	106.2	C8A—C14A—H14A	105.2
C13—C14—H14	106.2	C13A—C14A—H14A	105.2
C15—C14—H14	106.2	C15A—C14A—H14A	105.2
C16—C15—C14	101.18 (18)	C16A—C15A—C14A	101.25 (16)
C16—C15—H15A	111.5	C16A—C15A—H15C	111.5
C14—C15—H15A	111.5	C14A—C15A—H15C	111.5
C16—C15—H15B	111.5	C16A—C15A—H15D	111.5
C14—C15—H15B	111.5	C14A—C15A—H15D	111.5
H15A—C15—H15B	109.4	H15C—C15A—H15D	109.3
C20—C16—C17	120.9 (2)	C20A—C16A—C17A	119.4 (2)
C20—C16—C15	130.6 (2)	C20A—C16A—C15A	132.5 (2)
C17—C16—C15	108.41 (18)	C17A—C16A—C15A	108.03 (17)
O27—C17—C16	126.7 (2)	O27A—C17A—C16A	125.9 (2)
O27—C17—C13	126.0 (2)	O27A—C17A—C13A	127.1 (2)
C16—C17—C13	107.21 (18)	C16A—C17A—C13A	106.97 (17)
C13—C18—H18A	109.5	C13A—C18A—H18D	109.5
C13—C18—H18B	109.5	C13A—C18A—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18A—H18E	109.5
C13—C18—H18C	109.5	C13A—C18A—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18A—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18A—H18F	109.5
C10—C19—H19A	109.5	C10A—C19A—H19D	109.5
C10—C19—H19B	109.5	C10A—C19A—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19A—H19E	109.5
C10—C19—H19C	109.5	C10A—C19A—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19A—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19A—H19F	109.5
C16—C20—C21	127.7 (2)	C16A—C20A—C21A	130.0 (2)
C16—C20—H20	116.1	C16A—C20A—H20A	115.0
C21—C20—H20	116.1	C21A—C20A—H20A	115.0
N26—C21—C22	122.2 (2)	N26A—C21A—C22A	122.1 (2)
N26—C21—C20	118.0 (2)	N26A—C21A—C20A	113.8 (2)
C22—C21—C20	119.7 (2)	C22A—C21A—C20A	124.1 (2)
C23—C22—C21	119.6 (2)	C21A—C22A—C23A	119.4 (3)
C23—C22—H22	120.2	C21A—C22A—H22A	120.3
C21—C22—H22	120.2	C23A—C22A—H22A	120.3
C24—C23—C22	118.1 (2)	C24A—C23A—C22A	118.4 (3)
C24—C23—H23	121.0	C24A—C23A—H23A	120.8
C22—C23—H23	121.0	C22A—C23A—H23A	120.8
C23—C24—C25	119.0 (3)	C25A—C24A—C23A	118.3 (3)
C23—C24—H24	120.5	C25A—C24A—H24A	120.8
C25—C24—H24	120.5	C23A—C24A—H24A	120.8
N26—C25—C24	124.1 (3)	N26A—C25A—C24A	124.6 (3)
N26—C25—H25	117.9	N26A—C25A—H25A	117.7
C24—C25—H25	117.9	C24A—C25A—H25A	117.7
C25—N26—C21	117.0 (2)	C25A—N26A—C21A	117.1 (3)
C10—C1—C2—C3	−56.2 (3)	C4A—C5A—C6A—C7A	136.3 (2)
C1—C2—C3—O28	−150.2 (3)	C10A—C5A—C6A—C7A	−48.5 (3)
C1—C2—C3—C4	33.5 (3)	C5A—C6A—C7A—C8A	52.0 (3)
O28—C3—C4—C5	−179.1 (3)	C6A—C7A—C8A—C14A	−175.76 (18)
C2—C3—C4—C5	−2.9 (4)	C6A—C7A—C8A—C9A	−56.4 (2)
C3—C4—C5—C6	169.7 (2)	C14A—C8A—C9A—C11A	−52.3 (2)
C3—C4—C5—C10	−6.5 (4)	C7A—C8A—C9A—C11A	−173.49 (17)
C4—C5—C6—C7	135.7 (2)	C14A—C8A—C9A—C10A	178.78 (16)
C10—C5—C6—C7	−47.9 (3)	C7A—C8A—C9A—C10A	57.6 (2)
C5—C6—C7—C8	50.1 (3)	C4A—C5A—C10A—C19A	101.0 (2)
C6—C7—C8—C14	−176.1 (2)	C6A—C5A—C10A—C19A	−74.1 (2)
C6—C7—C8—C9	−55.7 (3)	C4A—C5A—C10A—C1A	−19.0 (3)
C7—C8—C9—C11	−171.91 (18)	C6A—C5A—C10A—C1A	165.91 (19)
C14—C8—C9—C11	−50.1 (2)	C4A—C5A—C10A—C9A	−138.1 (2)
C7—C8—C9—C10	59.5 (2)	C6A—C5A—C10A—C9A	46.7 (2)
C14—C8—C9—C10	−178.70 (17)	C2A—C1A—C10A—C5A	47.2 (3)
C4—C5—C10—C1	−15.3 (3)	C2A—C1A—C10A—C19A	−70.8 (3)
C6—C5—C10—C1	168.26 (19)	C2A—C1A—C10A—C9A	166.6 (2)
C4—C5—C10—C19	103.8 (2)	C11A—C9A—C10A—C5A	−179.92 (18)
C6—C5—C10—C19	−72.6 (2)	C8A—C9A—C10A—C5A	−51.3 (2)
C4—C5—C10—C9	−134.7 (2)	C11A—C9A—C10A—C19A	−61.7 (2)
C6—C5—C10—C9	48.9 (2)	C8A—C9A—C10A—C19A	66.9 (2)
C2—C1—C10—C5	46.3 (2)	C11A—C9A—C10A—C1A	60.3 (2)
C2—C1—C10—C19	−71.7 (2)	C8A—C9A—C10A—C1A	−171.10 (17)
C2—C1—C10—C9	165.1 (2)	C8A—C9A—C11A—C12A	54.3 (2)
C11—C9—C10—C5	176.64 (18)	C10A—C9A—C11A—C12A	−176.48 (17)
C8—C9—C10—C5	−54.4 (2)	C9A—C11A—C12A—C13A	−55.2 (2)
C11—C9—C10—C1	56.9 (2)	C11A—C12A—C13A—C17A	166.76 (18)
C8—C9—C10—C1	−174.10 (17)	C11A—C12A—C13A—C14A	55.2 (2)
C11—C9—C10—C19	−64.7 (2)	C11A—C12A—C13A—C18A	−71.1 (2)
C8—C9—C10—C19	64.3 (2)	C7A—C8A—C14A—C13A	175.88 (17)
C8—C9—C11—C12	51.3 (3)	C9A—C8A—C14A—C13A	55.7 (2)
C10—C9—C11—C12	179.79 (18)	C7A—C8A—C14A—C15A	−58.0 (2)
C9—C11—C12—C13	−54.7 (3)	C9A—C8A—C14A—C15A	−178.20 (17)
C11—C12—C13—C17	171.8 (2)	C17A—C13A—C14A—C8A	179.57 (16)
C11—C12—C13—C14	58.5 (2)	C12A—C13A—C14A—C8A	−58.4 (2)
C11—C12—C13—C18	−68.2 (2)	C18A—C13A—C14A—C8A	66.7 (2)
C7—C8—C14—C13	176.8 (2)	C17A—C13A—C14A—C15A	44.97 (19)
C9—C8—C14—C13	56.1 (2)	C12A—C13A—C14A—C15A	167.00 (17)
C7—C8—C14—C15	−59.3 (3)	C18A—C13A—C14A—C15A	−67.9 (2)
C9—C8—C14—C15	179.96 (19)	C8A—C14A—C15A—C16A	−169.66 (18)
C17—C13—C14—C8	174.59 (19)	C13A—C14A—C15A—C16A	−38.9 (2)
C12—C13—C14—C8	−61.9 (2)	C14A—C15A—C16A—C20A	−159.1 (2)
C18—C13—C14—C8	63.6 (2)	C14A—C15A—C16A—C17A	17.3 (2)
C17—C13—C14—C15	42.5 (2)	C20A—C16A—C17A—O27A	8.7 (4)
C12—C13—C14—C15	166.03 (17)	C15A—C16A—C17A—O27A	−168.3 (2)
C18—C13—C14—C15	−68.5 (2)	C20A—C16A—C17A—C13A	−172.42 (19)
C8—C14—C15—C16	−166.2 (2)	C15A—C16A—C17A—C13A	10.6 (2)
C13—C14—C15—C16	−38.3 (2)	C12A—C13A—C17A—O27A	27.6 (3)
C14—C15—C16—C20	−157.9 (3)	C14A—C13A—C17A—O27A	145.1 (2)
C14—C15—C16—C17	19.2 (3)	C18A—C13A—C17A—O27A	−96.8 (3)
C20—C16—C17—O27	1.9 (4)	C12A—C13A—C17A—C16A	−151.32 (18)
C15—C16—C17—O27	−175.5 (3)	C14A—C13A—C17A—C16A	−33.8 (2)
C20—C16—C17—C13	−175.6 (2)	C18A—C13A—C17A—C16A	84.3 (2)
C15—C16—C17—C13	6.9 (3)	C17A—C16A—C20A—C21A	177.9 (2)
C12—C13—C17—O27	34.1 (3)	C15A—C16A—C20A—C21A	−6.1 (4)
C14—C13—C17—O27	152.3 (3)	C16A—C20A—C21A—N26A	161.7 (2)
C18—C13—C17—O27	−89.6 (3)	C16A—C20A—C21A—C22A	−20.7 (4)
C12—C13—C17—C16	−148.3 (2)	N26A—C21A—C22A—C23A	0.1 (4)
C14—C13—C17—C16	−30.1 (2)	C20A—C21A—C22A—C23A	−177.3 (3)
C18—C13—C17—C16	88.0 (2)	C21A—C22A—C23A—C24A	0.0 (5)
C17—C16—C20—C21	174.8 (2)	C22A—C23A—C24A—C25A	−0.4 (5)
C15—C16—C20—C21	−8.4 (5)	C23A—C24A—C25A—N26A	0.9 (5)
C16—C20—C21—N26	−25.1 (4)	C24A—C25A—N26A—C21A	−0.8 (5)
C16—C20—C21—C22	157.4 (3)	C22A—C21A—N26A—C25A	0.3 (4)
N26—C21—C22—C23	1.3 (4)	C20A—C21A—N26A—C25A	178.0 (2)
C20—C21—C22—C23	178.6 (2)	C17—C16—C20—H20	−5.2
C21—C22—C23—C24	−1.2 (4)	C15—C16—C20—H20	171.6
C22—C23—C24—C25	0.2 (5)	C22—C21—C20—H20	−22.6
C23—C24—C25—N26	1.0 (7)	N26—C21—C20—H20	154.9
C24—C25—N26—C21	−0.9 (6)	C18—C13—C14—H14	179.5
C22—C21—N26—C25	−0.2 (5)	H9—C9—C8—H8	−175.3
C20—C21—N26—C25	−177.6 (3)	C19—C10—C13—C18	−1.08 (17)
C10A—C1A—C2A—C3A	−51.0 (3)	C17A—C16A—C20A—H20A	−2.1
C1A—C2A—C3A—O28A	−158.6 (3)	C15A—C16A—C20A—H20A	173.9
C1A—C2A—C3A—C4A	24.4 (4)	C22A—C21A—C20A—H20A	159.3
O28A—C3A—C4A—C5A	−172.0 (3)	N26A—C21A—C20A—H20A	−18.3
C2A—C3A—C4A—C5A	5.0 (4)	C18A—C13A—C14A—H14A	−178.3
C3A—C4A—C5A—C6A	167.6 (2)	H9A—C9A—C8A—H8A	−178.1
C3A—C4A—C5A—C10A	−7.4 (4)	C19A—C10A—C13A—C18A	1.49 (18)