6β-Acetamido-5α-hydroxy-cholestan-3β-yl acetate.

The title steroid, C(31)H(53)NO(4), was prepared from the corresponding 5α,6α-epoxy-cholestane. The conformation of the six-membered rings is close to a chair form, while the five-membered ring adopts a twist conformation. The hydroxyl and acetamide groups are in axial positions. The nucleophilic species bound to the steroid nucleus at position 6 by the β-face, whereas the hydroxyl group at position 5 has α-orientation. All rings are trans-fused. The crystal packing shows that the mol-ecules related by twofold symmetry exist as O-H⋯O hydrogen-bonded dimers.

Related literature

For epoxy­steroid chemistry, see: Salvador et al. (2006 ▶, 2008 ▶); Pinto et al. (2008a ▶). For the synthesis of vicinal N-acyl hydroxy­amines, see: Pinto et al. (2006 ▶). For related steroid structures, see: Pinto et al. (2007a ▶,b ▶, 2008b ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C31H53NO4

M = 503.74

Monoclinic,

a = 31.4800 (12) Å

b = 10.0043 (4) Å

c = 9.7681 (4) Å

β = 94.276 (3)°

V = 3067.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 (2) K

0.40 × 0.20 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.840, T max = 0.990

43053 measured reflections

4691 independent reflections

2907 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.162

S = 1.03

4691 reflections

333 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803568X/ci2694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803568X/ci2694Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C31H53NO4	F000 = 1112
Mr = 503.74	Dx = 1.091 Mg m−3
Monoclinic, C2	Mo Kα radiation λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 5555 reflections
a = 31.4800 (12) Å	θ = 2.4–22.9º
b = 10.0043 (4) Å	µ = 0.07 mm−1
c = 9.7681 (4) Å	T = 293 (2) K
β = 94.276 (3)º	Truncated parallelipiped, clear colourless
V = 3067.8 (2) Å3	0.40 × 0.20 × 0.14 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	4691 independent reflections
Radiation source: fine-focus sealed tube	2907 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.045
T = 293(2) K	θmax = 30.1º
φ and ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)	h = −43→44
Tmin = 0.840, Tmax = 0.990	k = −13→13
43053 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.162	w = 1/[σ2(Fo2) + (0.0835P)2 + 0.6891P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
4691 reflections	Δρmax = 0.34 e Å−3
333 parameters	Δρmin = −0.24 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 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.

	x	y	z	Uiso*/Ueq
C1	0.87141 (10)	−0.0088 (3)	0.1952 (3)	0.0615 (8)
H1A	0.8421	−0.0361	0.1741	0.074*
H1B	0.8806	0.0391	0.1163	0.074*
C2	0.89921 (11)	−0.1341 (3)	0.2196 (4)	0.0727 (9)
H2A	0.8880	−0.1876	0.2916	0.087*
H2B	0.8978	−0.1874	0.1365	0.087*
C3	0.94513 (11)	−0.0993 (4)	0.2603 (4)	0.0678 (9)
H3	0.9583	−0.0598	0.1820	0.081*
C4	0.94903 (10)	−0.0042 (3)	0.3809 (3)	0.0592 (7)
H4A	0.9786	0.0217	0.3991	0.071*
H4B	0.9400	−0.0490	0.4618	0.071*
C5	0.92162 (8)	0.1215 (3)	0.3521 (3)	0.0484 (6)
C6	0.92943 (8)	0.2272 (3)	0.4659 (3)	0.0500 (6)
H6	0.9595	0.2526	0.4664	0.060*
C7	0.90374 (8)	0.3533 (3)	0.4310 (3)	0.0508 (6)
H7A	0.9156	0.3976	0.3541	0.061*
H7B	0.9066	0.4136	0.5089	0.061*
C8	0.85643 (8)	0.3267 (3)	0.3944 (3)	0.0424 (5)
H8	0.8434	0.2971	0.4773	0.051*
C9	0.84930 (8)	0.2180 (3)	0.2834 (3)	0.0443 (5)
H9	0.8610	0.2530	0.2005	0.053*
C10	0.87356 (8)	0.0865 (3)	0.3205 (3)	0.0466 (6)
C11	0.80110 (9)	0.1986 (3)	0.2483 (3)	0.0550 (7)
H11A	0.7968	0.1321	0.1763	0.066*
H11B	0.7882	0.1653	0.3287	0.066*
C12	0.77895 (9)	0.3288 (3)	0.2008 (3)	0.0525 (7)
H12A	0.7898	0.3571	0.1152	0.063*
H12B	0.7487	0.3123	0.1836	0.063*
C13	0.78570 (8)	0.4407 (3)	0.3063 (3)	0.0421 (6)
C14	0.83406 (8)	0.4540 (3)	0.3415 (3)	0.0424 (5)
H14	0.8462	0.4743	0.2543	0.051*
C15	0.83868 (9)	0.5810 (3)	0.4253 (3)	0.0549 (7)
H15A	0.8667	0.6201	0.4198	0.066*
H15B	0.8340	0.5642	0.5209	0.066*
C16	0.80370 (9)	0.6726 (3)	0.3580 (3)	0.0601 (7)
H16A	0.8164	0.7448	0.3089	0.072*
H16B	0.7869	0.7109	0.4274	0.072*
C17	0.77525 (8)	0.5856 (3)	0.2575 (3)	0.0451 (6)
H17	0.7864	0.5953	0.1670	0.054*
C18	0.76160 (9)	0.4092 (3)	0.4336 (3)	0.0542 (7)
H18A	0.7319	0.3972	0.4067	0.081*
H18B	0.7650	0.4820	0.4976	0.081*
H18C	0.7728	0.3289	0.4761	0.081*
C19	0.85347 (10)	0.0158 (3)	0.4394 (3)	0.0579 (7)
H19A	0.8272	−0.0254	0.4058	0.087*
H19B	0.8480	0.0799	0.5090	0.087*
H19C	0.8727	−0.0514	0.4775	0.087*
C20	0.72882 (8)	0.6341 (3)	0.2425 (3)	0.0500 (6)
H20	0.7178	0.6302	0.3337	0.060*
C21	0.70059 (12)	0.5469 (4)	0.1483 (5)	0.0822 (12)
H21A	0.7130	0.5372	0.0621	0.123*
H21B	0.6730	0.5874	0.1335	0.123*
H21C	0.6978	0.4605	0.1895	0.123*
C22	0.72669 (9)	0.7808 (3)	0.1956 (3)	0.0543 (7)
H22A	0.7450	0.8335	0.2591	0.065*
H22B	0.7380	0.7869	0.1061	0.065*
C23	0.68225 (10)	0.8419 (3)	0.1864 (4)	0.0604 (8)
H23A	0.6656	0.8026	0.1090	0.072*
H23B	0.6685	0.8193	0.2689	0.072*
C24	0.68225 (10)	0.9932 (3)	0.1698 (3)	0.0602 (8)
H24A	0.6956	1.0152	0.0862	0.072*
H24B	0.6996	1.0318	0.2460	0.072*
C25	0.63810 (11)	1.0583 (4)	0.1637 (4)	0.0655 (8)
H25	0.6235	1.0251	0.2420	0.079*
C26	0.61094 (14)	1.0219 (5)	0.0335 (4)	0.0889 (12)
H26A	0.6241	1.0561	−0.0449	0.133*
H26B	0.5831	1.0603	0.0369	0.133*
H26C	0.6085	0.9265	0.0265	0.133*
C27	0.64222 (15)	1.2093 (4)	0.1785 (5)	0.0938 (13)
H27A	0.6586	1.2437	0.1073	0.141*
H27B	0.6563	1.2304	0.2664	0.141*
H27C	0.6144	1.2491	0.1710	0.141*
O3A	0.96596 (8)	−0.2259 (3)	0.2984 (3)	0.0831 (7)
C3A	1.00685 (17)	−0.2395 (6)	0.2845 (7)	0.118 (2)
C3B	1.0213 (2)	−0.3779 (7)	0.3176 (9)	0.162 (3)
H3BA	1.0490	−0.3754	0.3656	0.242*
H3BB	1.0226	−0.4279	0.2341	0.242*
H3BC	1.0015	−0.4199	0.3743	0.242*
O3B	1.02871 (13)	−0.1488 (5)	0.2544 (7)	0.169 (2)
O5	0.93451 (6)	0.1818 (2)	0.2284 (2)	0.0583 (5)
H5A	0.9594	0.2062	0.2402	0.087*
N6	0.92306 (7)	0.1766 (3)	0.6033 (2)	0.0574 (6)
H6A	0.9009	0.1287	0.6138	0.069*
O6	0.98188 (8)	0.2694 (4)	0.7050 (3)	0.0856 (8)
C6A	0.94987 (10)	0.2006 (4)	0.7137 (3)	0.0608 (8)
C6B	0.93864 (13)	0.1416 (6)	0.8461 (4)	0.0881 (12)
H6BA	0.9595	0.0756	0.8757	0.132*
H6BB	0.9111	0.1004	0.8339	0.132*
H6BC	0.9381	0.2106	0.9142	0.132*

	U11	U22	U33	U12	U13	U23
C1	0.0589 (17)	0.0517 (17)	0.0728 (19)	0.0080 (14)	−0.0019 (14)	−0.0103 (15)
C2	0.070 (2)	0.0522 (18)	0.095 (2)	0.0131 (16)	0.0014 (17)	−0.0149 (17)
C3	0.0612 (18)	0.0521 (17)	0.091 (2)	0.0156 (15)	0.0111 (16)	0.0011 (16)
C4	0.0463 (15)	0.0544 (17)	0.077 (2)	0.0114 (13)	0.0071 (13)	0.0047 (15)
C5	0.0400 (13)	0.0490 (14)	0.0561 (15)	0.0049 (11)	0.0040 (11)	0.0057 (12)
C6	0.0358 (12)	0.0532 (16)	0.0604 (16)	−0.0013 (11)	0.0005 (11)	0.0039 (12)
C7	0.0416 (13)	0.0474 (15)	0.0627 (16)	−0.0027 (11)	−0.0015 (11)	−0.0031 (13)
C8	0.0371 (12)	0.0432 (13)	0.0467 (13)	−0.0005 (10)	0.0022 (10)	−0.0014 (10)
C9	0.0394 (12)	0.0420 (13)	0.0510 (14)	0.0014 (10)	0.0005 (10)	−0.0037 (10)
C10	0.0399 (13)	0.0411 (13)	0.0582 (15)	0.0009 (11)	0.0008 (11)	−0.0016 (11)
C11	0.0461 (14)	0.0497 (16)	0.0670 (17)	−0.0003 (12)	−0.0101 (12)	−0.0092 (13)
C12	0.0451 (14)	0.0510 (15)	0.0594 (16)	0.0052 (12)	−0.0083 (12)	−0.0098 (13)
C13	0.0389 (12)	0.0424 (13)	0.0450 (13)	−0.0002 (10)	0.0042 (10)	−0.0006 (10)
C14	0.0412 (13)	0.0404 (12)	0.0453 (13)	−0.0013 (10)	0.0022 (10)	−0.0006 (10)
C15	0.0482 (15)	0.0448 (14)	0.0704 (18)	0.0002 (12)	−0.0042 (13)	−0.0082 (13)
C16	0.0506 (15)	0.0471 (15)	0.082 (2)	0.0019 (13)	0.0019 (14)	−0.0093 (15)
C17	0.0444 (13)	0.0452 (13)	0.0462 (13)	0.0028 (11)	0.0056 (10)	0.0035 (11)
C18	0.0461 (14)	0.0585 (16)	0.0587 (16)	0.0008 (13)	0.0087 (12)	0.0103 (13)
C19	0.0488 (15)	0.0455 (15)	0.079 (2)	−0.0035 (12)	0.0051 (14)	0.0035 (14)
C20	0.0467 (14)	0.0486 (14)	0.0546 (15)	0.0056 (12)	0.0024 (11)	0.0031 (12)
C21	0.063 (2)	0.062 (2)	0.116 (3)	0.0088 (17)	−0.030 (2)	−0.008 (2)
C22	0.0556 (15)	0.0533 (16)	0.0545 (15)	0.0110 (13)	0.0067 (12)	0.0078 (13)
C23	0.0563 (17)	0.0579 (18)	0.0671 (18)	0.0147 (14)	0.0054 (13)	0.0103 (14)
C24	0.0612 (18)	0.0575 (18)	0.0628 (18)	0.0135 (14)	0.0099 (14)	0.0073 (14)
C25	0.0664 (19)	0.0594 (19)	0.0717 (19)	0.0188 (16)	0.0113 (16)	0.0060 (16)
C26	0.084 (3)	0.083 (3)	0.097 (3)	0.030 (2)	−0.008 (2)	0.001 (2)
C27	0.100 (3)	0.064 (2)	0.117 (3)	0.027 (2)	0.003 (2)	0.000 (2)
O3A	0.0696 (15)	0.0601 (14)	0.122 (2)	0.0235 (12)	0.0206 (13)	0.0056 (14)
C3A	0.088 (3)	0.082 (3)	0.191 (6)	0.038 (3)	0.054 (3)	0.027 (4)
C3B	0.134 (5)	0.105 (4)	0.253 (9)	0.077 (4)	0.064 (5)	0.042 (5)
O3B	0.091 (3)	0.117 (4)	0.308 (7)	0.035 (2)	0.077 (3)	0.051 (4)
O5	0.0489 (10)	0.0654 (13)	0.0616 (11)	0.0037 (10)	0.0108 (8)	0.0083 (11)
N6	0.0421 (12)	0.0699 (16)	0.0593 (13)	−0.0037 (12)	−0.0022 (10)	0.0048 (13)
O6	0.0545 (13)	0.125 (2)	0.0768 (15)	−0.0114 (15)	−0.0017 (11)	−0.0260 (16)
C6A	0.0482 (15)	0.072 (2)	0.0617 (17)	0.0159 (15)	−0.0013 (13)	−0.0125 (15)
C6B	0.084 (2)	0.115 (3)	0.064 (2)	0.013 (3)	0.0005 (17)	−0.002 (2)

C1—C2	1.537 (4)	C17—C20	1.536 (4)
C1—C10	1.549 (4)	C17—H17	0.98
C1—H1A	0.97	C18—H18A	0.96
C1—H1B	0.97	C18—H18B	0.96
C2—C3	1.511 (5)	C18—H18C	0.96
C2—H2A	0.97	C19—H19A	0.96
C2—H2B	0.97	C19—H19B	0.96
C3—O3A	1.461 (4)	C19—H19C	0.96
C3—C4	1.512 (5)	C20—C21	1.509 (5)
C3—H3	0.98	C20—C22	1.537 (4)
C4—C5	1.539 (4)	C20—H20	0.98
C4—H4A	0.97	C21—H21A	0.96
C4—H4B	0.97	C21—H21B	0.96
C5—O5	1.436 (3)	C21—H21C	0.96
C5—C6	1.541 (4)	C22—C23	1.523 (4)
C5—C10	1.561 (4)	C22—H22A	0.97
C6—N6	1.461 (4)	C22—H22B	0.97
C6—C7	1.523 (4)	C23—C24	1.523 (5)
C6—H6	0.98	C23—H23A	0.97
C7—C8	1.528 (4)	C23—H23B	0.97
C7—H7A	0.97	C24—C25	1.532 (4)
C7—H7B	0.97	C24—H24A	0.97
C8—C14	1.527 (4)	C24—H24B	0.97
C8—C9	1.540 (3)	C25—C27	1.522 (6)
C8—H8	0.98	C25—C26	1.522 (6)
C9—C11	1.543 (4)	C25—H25	0.98
C9—C10	1.551 (4)	C26—H26A	0.96
C9—H9	0.98	C26—H26B	0.96
C10—C19	1.535 (4)	C26—H26C	0.96
C11—C12	1.532 (4)	C27—H27A	0.96
C11—H11A	0.97	C27—H27B	0.96
C11—H11B	0.97	C27—H27C	0.96
C12—C13	1.526 (4)	O3A—C3A	1.312 (5)
C12—H12A	0.97	C3A—O3B	1.190 (7)
C12—H12B	0.97	C3A—C3B	1.485 (7)
C13—C18	1.537 (4)	C3B—H3BA	0.96
C13—C14	1.541 (3)	C3B—H3BB	0.96
C13—C17	1.554 (4)	C3B—H3BC	0.96
C14—C15	1.513 (4)	O5—H5A	0.82
C14—H14	0.98	N6—C6A	1.341 (4)
C15—C16	1.542 (4)	N6—H6A	0.86
C15—H15A	0.97	O6—C6A	1.228 (4)
C15—H15B	0.97	C6A—C6B	1.488 (5)
C16—C17	1.547 (4)	C6B—H6BA	0.96
C16—H16A	0.97	C6B—H6BB	0.96
C16—H16B	0.97	C6B—H6BC	0.96
C2—C1—C10	112.9 (3)	C15—C16—H16B	110.2
C2—C1—H1A	109.0	C17—C16—H16B	110.2
C10—C1—H1A	109.0	H16A—C16—H16B	108.5
C2—C1—H1B	109.0	C20—C17—C16	112.6 (2)
C10—C1—H1B	109.0	C20—C17—C13	120.1 (2)
H1A—C1—H1B	107.8	C16—C17—C13	103.3 (2)
C3—C2—C1	112.1 (3)	C20—C17—H17	106.7
C3—C2—H2A	109.2	C16—C17—H17	106.7
C1—C2—H2A	109.2	C13—C17—H17	106.7
C3—C2—H2B	109.2	C13—C18—H18A	109.5
C1—C2—H2B	109.2	C13—C18—H18B	109.5
H2A—C2—H2B	107.9	H18A—C18—H18B	109.5
O3A—C3—C2	105.7 (3)	C13—C18—H18C	109.5
O3A—C3—C4	109.8 (3)	H18A—C18—H18C	109.5
C2—C3—C4	111.7 (3)	H18B—C18—H18C	109.5
O3A—C3—H3	109.9	C10—C19—H19A	109.5
C2—C3—H3	109.9	C10—C19—H19B	109.5
C4—C3—H3	109.9	H19A—C19—H19B	109.5
C3—C4—C5	111.1 (3)	C10—C19—H19C	109.5
C3—C4—H4A	109.4	H19A—C19—H19C	109.5
C5—C4—H4A	109.4	H19B—C19—H19C	109.5
C3—C4—H4B	109.4	C21—C20—C17	112.8 (3)
C5—C4—H4B	109.4	C21—C20—C22	111.1 (3)
H4A—C4—H4B	108.0	C17—C20—C22	110.5 (2)
O5—C5—C4	107.9 (2)	C21—C20—H20	107.4
O5—C5—C6	106.2 (2)	C17—C20—H20	107.4
C4—C5—C6	111.9 (2)	C22—C20—H20	107.4
O5—C5—C10	105.0 (2)	C20—C21—H21A	109.5
C4—C5—C10	112.0 (2)	C20—C21—H21B	109.5
C6—C5—C10	113.4 (2)	H21A—C21—H21B	109.5
N6—C6—C7	112.7 (2)	C20—C21—H21C	109.5
N6—C6—C5	113.5 (2)	H21A—C21—H21C	109.5
C7—C6—C5	110.7 (2)	H21B—C21—H21C	109.5
N6—C6—H6	106.5	C23—C22—C20	114.9 (3)
C7—C6—H6	106.5	C23—C22—H22A	108.6
C5—C6—H6	106.5	C20—C22—H22A	108.6
C6—C7—C8	113.6 (2)	C23—C22—H22B	108.6
C6—C7—H7A	108.9	C20—C22—H22B	108.6
C8—C7—H7A	108.9	H22A—C22—H22B	107.5
C6—C7—H7B	108.9	C24—C23—C22	113.5 (3)
C8—C7—H7B	108.9	C24—C23—H23A	108.9
H7A—C7—H7B	107.7	C22—C23—H23A	108.9
C14—C8—C7	110.5 (2)	C24—C23—H23B	108.9
C14—C8—C9	108.11 (19)	C22—C23—H23B	108.9
C7—C8—C9	112.1 (2)	H23A—C23—H23B	107.7
C14—C8—H8	108.7	C23—C24—C25	114.8 (3)
C7—C8—H8	108.7	C23—C24—H24A	108.6
C9—C8—H8	108.7	C25—C24—H24A	108.6
C8—C9—C11	109.6 (2)	C23—C24—H24B	108.6
C8—C9—C10	113.0 (2)	C25—C24—H24B	108.6
C11—C9—C10	113.8 (2)	H24A—C24—H24B	107.5
C8—C9—H9	106.6	C27—C25—C26	110.8 (3)
C11—C9—H9	106.6	C27—C25—C24	110.3 (3)
C10—C9—H9	106.6	C26—C25—C24	112.5 (3)
C19—C10—C1	108.5 (3)	C27—C25—H25	107.7
C19—C10—C9	110.1 (2)	C26—C25—H25	107.7
C1—C10—C9	110.2 (2)	C24—C25—H25	107.7
C19—C10—C5	113.7 (2)	C25—C26—H26A	109.5
C1—C10—C5	106.2 (2)	C25—C26—H26B	109.5
C9—C10—C5	108.0 (2)	H26A—C26—H26B	109.5
C12—C11—C9	112.2 (2)	C25—C26—H26C	109.5
C12—C11—H11A	109.2	H26A—C26—H26C	109.5
C9—C11—H11A	109.2	H26B—C26—H26C	109.5
C12—C11—H11B	109.2	C25—C27—H27A	109.5
C9—C11—H11B	109.2	C25—C27—H27B	109.5
H11A—C11—H11B	107.9	H27A—C27—H27B	109.5
C13—C12—C11	112.4 (2)	C25—C27—H27C	109.5
C13—C12—H12A	109.1	H27A—C27—H27C	109.5
C11—C12—H12A	109.1	H27B—C27—H27C	109.5
C13—C12—H12B	109.1	C3A—O3A—C3	119.3 (4)
C11—C12—H12B	109.1	O3B—C3A—O3A	122.4 (5)
H12A—C12—H12B	107.8	O3B—C3A—C3B	126.3 (5)
C12—C13—C18	110.1 (2)	O3A—C3A—C3B	111.2 (5)
C12—C13—C14	107.4 (2)	C3A—C3B—H3BA	109.5
C18—C13—C14	112.1 (2)	C3A—C3B—H3BB	109.5
C12—C13—C17	117.5 (2)	H3BA—C3B—H3BB	109.5
C18—C13—C17	109.5 (2)	C3A—C3B—H3BC	109.5
C14—C13—C17	99.84 (19)	H3BA—C3B—H3BC	109.5
C15—C14—C8	119.6 (2)	H3BB—C3B—H3BC	109.5
C15—C14—C13	104.3 (2)	C5—O5—H5A	109.5
C8—C14—C13	115.2 (2)	C6A—N6—C6	123.7 (3)
C15—C14—H14	105.5	C6A—N6—H6A	118.1
C8—C14—H14	105.5	C6—N6—H6A	118.1
C13—C14—H14	105.5	O6—C6A—N6	121.0 (3)
C14—C15—C16	103.4 (2)	O6—C6A—C6B	122.2 (3)
C14—C15—H15A	111.1	N6—C6A—C6B	116.9 (3)
C16—C15—H15A	111.1	C6A—C6B—H6BA	109.5
C14—C15—H15B	111.1	C6A—C6B—H6BB	109.5
C16—C15—H15B	111.1	H6BA—C6B—H6BB	109.5
H15A—C15—H15B	109.1	C6A—C6B—H6BC	109.5
C15—C16—C17	107.3 (2)	H6BA—C6B—H6BC	109.5
C15—C16—H16A	110.2	H6BB—C6B—H6BC	109.5
C17—C16—H16A	110.2
C10—C1—C2—C3	−55.8 (4)	C11—C12—C13—C18	−69.1 (3)
C1—C2—C3—O3A	172.3 (3)	C11—C12—C13—C14	53.2 (3)
C1—C2—C3—C4	52.9 (4)	C11—C12—C13—C17	164.6 (2)
O3A—C3—C4—C5	−171.2 (2)	C7—C8—C14—C15	−52.3 (3)
C2—C3—C4—C5	−54.3 (4)	C9—C8—C14—C15	−175.3 (2)
C3—C4—C5—O5	−56.5 (3)	C7—C8—C14—C13	−177.8 (2)
C3—C4—C5—C6	−172.9 (2)	C9—C8—C14—C13	59.2 (3)
C3—C4—C5—C10	58.5 (3)	C12—C13—C14—C15	170.2 (2)
O5—C5—C6—N6	−172.7 (2)	C18—C13—C14—C15	−68.7 (3)
C4—C5—C6—N6	−55.2 (3)	C17—C13—C14—C15	47.1 (2)
C10—C5—C6—N6	72.6 (3)	C12—C13—C14—C8	−56.7 (3)
O5—C5—C6—C7	59.5 (3)	C18—C13—C14—C8	64.4 (3)
C4—C5—C6—C7	176.9 (2)	C17—C13—C14—C8	−179.8 (2)
C10—C5—C6—C7	−55.3 (3)	C8—C14—C15—C16	−166.5 (2)
N6—C6—C7—C8	−76.5 (3)	C13—C14—C15—C16	−36.0 (3)
C5—C6—C7—C8	51.8 (3)	C14—C15—C16—C17	10.6 (3)
C6—C7—C8—C14	−172.1 (2)	C15—C16—C17—C20	149.3 (2)
C6—C7—C8—C9	−51.4 (3)	C15—C16—C17—C13	18.2 (3)
C14—C8—C9—C11	−56.4 (3)	C12—C13—C17—C20	78.9 (3)
C7—C8—C9—C11	−178.5 (2)	C18—C13—C17—C20	−47.6 (3)
C14—C8—C9—C10	175.5 (2)	C14—C13—C17—C20	−165.5 (2)
C7—C8—C9—C10	53.4 (3)	C12—C13—C17—C16	−154.7 (2)
C2—C1—C10—C19	−66.1 (3)	C18—C13—C17—C16	78.8 (3)
C2—C1—C10—C9	173.3 (3)	C14—C13—C17—C16	−39.0 (2)
C2—C1—C10—C5	56.5 (3)	C16—C17—C20—C21	−178.0 (3)
C8—C9—C10—C19	70.0 (3)	C13—C17—C20—C21	−56.0 (4)
C11—C9—C10—C19	−55.8 (3)	C16—C17—C20—C22	56.9 (3)
C8—C9—C10—C1	−170.2 (2)	C13—C17—C20—C22	179.0 (2)
C11—C9—C10—C1	63.9 (3)	C21—C20—C22—C23	57.8 (4)
C8—C9—C10—C5	−54.6 (3)	C17—C20—C22—C23	−176.2 (2)
C11—C9—C10—C5	179.5 (2)	C20—C22—C23—C24	167.7 (3)
O5—C5—C10—C19	178.1 (2)	C22—C23—C24—C25	−178.6 (3)
C4—C5—C10—C19	61.3 (3)	C23—C24—C25—C27	167.7 (4)
C6—C5—C10—C19	−66.4 (3)	C23—C24—C25—C26	−68.1 (4)
O5—C5—C10—C1	58.8 (3)	C2—C3—O3A—C3A	152.4 (5)
C4—C5—C10—C1	−58.0 (3)	C4—C3—O3A—C3A	−87.0 (5)
C6—C5—C10—C1	174.3 (2)	C3—O3A—C3A—O3B	7.4 (10)
O5—C5—C10—C9	−59.4 (3)	C3—O3A—C3A—C3B	−175.4 (5)
C4—C5—C10—C9	−176.2 (2)	C7—C6—N6—C6A	−98.2 (3)
C6—C5—C10—C9	56.1 (3)	C5—C6—N6—C6A	135.0 (3)
C8—C9—C11—C12	57.1 (3)	C6—N6—C6A—O6	0.7 (5)
C10—C9—C11—C12	−175.3 (2)	C6—N6—C6A—C6B	180.0 (3)
C9—C11—C12—C13	−56.5 (3)	C19—C10—C13—C18	6.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O6i	0.82	1.99	2.804 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O6i	0.82	1.99	2.804 (3)	172

Symmetry code: (i) .