N-tert-Butyl-3-hydr-oxy-5-androstene-17-carboxamide monohydrate.

In the title compound, C(24)H(39)NO(2)·H(2)O, the A and C rings of the pregnolene derivative sterol adopt chair conformations, with the B ring in a flattened chair conformation and the five-membered ring in an envelope conformation twisted about the C/D ring junction. The N-tert-butyl-carboxamide substituent is equatorial. The 3β-hydr-oxy H atom and one H atom of the water mol-ecule are disordered over two positions with equal occupancies. In the crystal structure, O-H⋯O hydrogen bonds between the 3β-hydr-oxy groups of neighbouring mol-ecules form dimers in the bc plane and these dimers are stacked along the a axis by additional O-H⋯O hydrogen bonds involving the water mol-ecules. The steric effect of the bulky tert-butyl substituent in the carboxamide chain precludes hydrogen-bond formation by the N-H group.

Related literature

The title compound is an inter­mediate in the synthesis of finasteride (Li et al., 2001 ▶). For pharmaceutical applications of finasteride, systematic name N-(tert-but­yl)-3-oxo-4-aza-5-androst-1-ene-17-carboxamide, see: Rasmusson et al. (1984 ▶, 1986 ▶); Rasmusson & Reynold (1985 ▶); US National Library of Medicine and National Institutes of Health (2008 ▶). For pregnenolone and its derivatives, see: Finar (1959 ▶). For the preparation of the title compound, see: Rasmusson et al. (1984 ▶); Dolling et al. (1999 ▶). For related structures, see: Bordner et al. (1978 ▶); Lancaster et al. (2007 ▶); Duax et al. (1989 ▶); Shukla et al. (2008 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C24H39NO2·H2O

M = 391.58

Monoclinic,

a = 9.934 (6) Å

b = 7.469 (5) Å

c = 30.647 (18) Å

β = 91.547 (10)°

V = 2273 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.40 × 0.30 × 0.15 mm

Data collection

Bruker SMART 1K CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.989

4186 measured reflections

2146 independent reflections

1735 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.114

S = 1.07

2146 reflections

277 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020984/wm2238sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020984/wm2238Isup2.hkl

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

C24H39NO2·H2O	F(000) = 864
Mr = 391.58	Dx = 1.144 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 734 reflections
a = 9.934 (6) Å	θ = 3.3–26.2°
b = 7.469 (5) Å	µ = 0.07 mm−1
c = 30.647 (18) Å	T = 293 K
β = 91.547 (10)°	Block, colourless
V = 2273 (2) Å3	0.40 × 0.30 × 0.15 mm
Z = 4

Bruker SMART 1K CCD diffractometer	2146 independent reflections
Radiation source: fine-focus sealed tube	1735 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.971, Tmax = 0.989	k = −5→8
4186 measured reflections	l = −32→36

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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.114	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.5179P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.003
2146 reflections	Δρmax = 0.18 e Å−3
277 parameters	Δρmin = −0.15 e Å−3
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0095 (13)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.4428 (4)	0.2304 (5)	0.35592 (10)	0.0384 (9)
H1A	0.4627	0.3396	0.3403	0.046*
H1B	0.3577	0.1847	0.3443	0.046*
C3	0.3985 (3)	0.1094 (5)	0.42947 (10)	0.0379 (9)
H3	0.3143	0.0565	0.4181	0.045*
O1	0.3816 (3)	0.1542 (4)	0.47468 (8)	0.0467 (7)
H1OA	0.450 (6)	0.128 (13)	0.489 (3)	0.070*	0.50
H1OB	0.358 (10)	0.052 (5)	0.480 (3)	0.070*	0.50
C4	0.5102 (4)	−0.0249 (5)	0.42418 (11)	0.0374 (9)
H4A	0.5926	0.0222	0.4374	0.045*
H4B	0.4877	−0.1344	0.4394	0.045*
C5	0.5333 (3)	−0.0670 (5)	0.37715 (10)	0.0300 (8)
C6	0.5374 (3)	−0.2341 (5)	0.36342 (11)	0.0350 (8)
H6	0.5238	−0.3239	0.3838	0.042*
C7	0.5621 (3)	−0.2899 (5)	0.31783 (11)	0.0346 (8)
H7A	0.4788	−0.3350	0.3048	0.042*
H7B	0.6269	−0.3871	0.3183	0.042*
C8	0.6145 (3)	−0.1399 (5)	0.28958 (10)	0.0273 (7)
H8	0.7102	−0.1216	0.2968	0.033*
C9	0.5391 (3)	0.0331 (4)	0.29865 (10)	0.0264 (7)
H9	0.4435	0.0065	0.2933	0.032*
C10	0.5527 (3)	0.0933 (4)	0.34704 (10)	0.0268 (7)
C19	0.6913 (3)	0.1751 (5)	0.35760 (10)	0.0388 (9)
H19A	0.7037	0.1859	0.3887	0.058*
H19B	0.6969	0.2914	0.3444	0.058*
H19C	0.7602	0.0992	0.3463	0.058*
C11	0.5739 (4)	0.1816 (5)	0.26685 (10)	0.0365 (8)
H11A	0.6649	0.2223	0.2735	0.044*
H11B	0.5138	0.2819	0.2713	0.044*
C12	0.5642 (4)	0.1268 (5)	0.21887 (10)	0.0372 (9)
H12A	0.4708	0.1039	0.2106	0.045*
H12B	0.5963	0.2239	0.2009	0.045*
C13	0.6473 (3)	−0.0400 (5)	0.21091 (10)	0.0292 (8)
C18	0.7972 (3)	0.0009 (5)	0.21675 (12)	0.0404 (9)
H18A	0.8486	−0.1026	0.2090	0.061*
H18B	0.8169	0.0317	0.2467	0.061*
H18C	0.8204	0.0994	0.1983	0.061*
C14	0.5993 (3)	−0.1847 (4)	0.24156 (10)	0.0288 (8)
H14	0.5022	−0.1957	0.2357	0.035*
C15	0.6607 (4)	−0.3561 (5)	0.22482 (12)	0.0451 (10)
H15A	0.6081	−0.4594	0.2331	0.054*
H15B	0.7524	−0.3708	0.2360	0.054*
C16	0.6573 (4)	−0.3311 (6)	0.17535 (12)	0.0553 (11)
H16A	0.5903	−0.4094	0.1618	0.066*
H16B	0.7444	−0.3592	0.1635	0.066*
C17	0.6212 (4)	−0.1340 (6)	0.16646 (11)	0.0389 (9)
H17	0.5244	−0.1277	0.1596	0.047*
C20	0.6943 (4)	−0.0543 (6)	0.12881 (12)	0.0448 (10)
O2	0.8041 (3)	−0.1105 (5)	0.11812 (9)	0.0679 (10)
N1	0.6348 (3)	0.0865 (5)	0.10950 (9)	0.0459 (9)
H1N	0.553 (2)	0.120 (6)	0.1186 (12)	0.055*
C21	0.6855 (4)	0.1911 (7)	0.07302 (11)	0.0499 (11)
C22	0.8179 (5)	0.2794 (9)	0.08648 (17)	0.0811 (16)
H22A	0.8044	0.3557	0.1112	0.122*
H22B	0.8501	0.3494	0.0626	0.122*
H22C	0.8830	0.1889	0.0941	0.122*
C23	0.5815 (5)	0.3306 (8)	0.06214 (15)	0.0794 (17)
H23A	0.4980	0.2733	0.0540	0.119*
H23B	0.6112	0.4024	0.0383	0.119*
H23C	0.5686	0.4054	0.0871	0.119*
C24	0.7039 (5)	0.0700 (9)	0.03397 (13)	0.0816 (17)
H24A	0.7758	−0.0129	0.0402	0.122*
H24B	0.7255	0.1410	0.0090	0.122*
H24C	0.6221	0.0050	0.0280	0.122*
O1W	0.3597 (4)	0.5303 (7)	0.49476 (16)	0.1038 (14)
H1W	0.416 (6)	0.553 (13)	0.5152 (16)	0.156*
H2WA	0.288 (15)	0.55 (3)	0.508 (7)	0.156*	0.50
H2WB	0.299 (18)	0.60 (2)	0.503 (8)	0.156*	0.50
C2	0.4264 (4)	0.2760 (5)	0.40398 (11)	0.0408 (9)
H2A	0.5080	0.3323	0.4154	0.049*
H2B	0.3527	0.3599	0.4070	0.049*

	U11	U22	U33	U12	U13	U23
C1	0.049 (2)	0.037 (2)	0.0293 (18)	0.0108 (17)	0.0050 (15)	0.0067 (17)
C3	0.0364 (19)	0.046 (2)	0.0312 (18)	−0.0048 (18)	−0.0004 (13)	−0.0004 (17)
O1	0.0488 (17)	0.061 (2)	0.0309 (14)	−0.0033 (15)	0.0086 (11)	−0.0015 (14)
C4	0.048 (2)	0.036 (2)	0.0277 (18)	−0.0011 (17)	0.0005 (15)	0.0079 (16)
C5	0.0281 (17)	0.032 (2)	0.0299 (17)	−0.0031 (15)	−0.0014 (13)	0.0066 (16)
C6	0.038 (2)	0.033 (2)	0.0345 (19)	−0.0038 (16)	0.0023 (14)	0.0095 (17)
C7	0.0400 (19)	0.0231 (19)	0.041 (2)	−0.0042 (15)	0.0028 (15)	0.0031 (16)
C8	0.0254 (16)	0.0282 (18)	0.0286 (17)	−0.0008 (15)	0.0034 (12)	0.0023 (15)
C9	0.0237 (15)	0.0247 (17)	0.0306 (17)	0.0005 (13)	0.0002 (12)	0.0023 (14)
C10	0.0296 (17)	0.0271 (18)	0.0237 (16)	0.0045 (14)	0.0023 (12)	0.0027 (14)
C19	0.0403 (19)	0.043 (2)	0.0332 (18)	−0.0118 (18)	0.0021 (14)	0.0019 (18)
C11	0.054 (2)	0.0279 (19)	0.0284 (18)	0.0077 (18)	0.0066 (15)	0.0042 (16)
C12	0.043 (2)	0.041 (2)	0.0278 (18)	0.0085 (17)	0.0038 (14)	0.0069 (17)
C13	0.0269 (17)	0.032 (2)	0.0288 (18)	−0.0008 (15)	0.0037 (13)	−0.0001 (16)
C18	0.0337 (19)	0.044 (2)	0.044 (2)	−0.0035 (17)	0.0026 (15)	0.0073 (18)
C14	0.0256 (16)	0.0274 (19)	0.0335 (18)	−0.0029 (14)	0.0020 (13)	−0.0041 (15)
C15	0.056 (2)	0.036 (2)	0.043 (2)	−0.0040 (19)	0.0084 (17)	−0.0065 (18)
C16	0.068 (3)	0.051 (3)	0.048 (2)	−0.007 (2)	0.0149 (19)	−0.014 (2)
C17	0.0376 (19)	0.049 (2)	0.0301 (18)	−0.0050 (18)	0.0024 (14)	−0.0062 (18)
C20	0.044 (2)	0.057 (3)	0.033 (2)	−0.001 (2)	0.0091 (16)	−0.007 (2)
O2	0.062 (2)	0.089 (3)	0.0546 (18)	0.0252 (18)	0.0296 (14)	0.0116 (18)
N1	0.0422 (17)	0.064 (2)	0.0315 (16)	0.0094 (17)	0.0086 (13)	0.0049 (17)
C21	0.052 (2)	0.066 (3)	0.032 (2)	0.009 (2)	0.0086 (16)	0.004 (2)
C22	0.068 (3)	0.096 (4)	0.079 (3)	−0.017 (3)	0.000 (3)	0.010 (3)
C23	0.088 (3)	0.095 (4)	0.056 (3)	0.027 (3)	0.019 (2)	0.021 (3)
C24	0.106 (4)	0.100 (5)	0.039 (2)	0.021 (4)	0.013 (2)	−0.005 (3)
O1W	0.076 (3)	0.106 (4)	0.131 (4)	0.021 (3)	0.019 (2)	−0.036 (3)
C2	0.049 (2)	0.041 (2)	0.0326 (19)	0.0135 (18)	0.0085 (15)	−0.0001 (18)

C1—C2	1.525 (5)	C13—C18	1.526 (5)
C1—C10	1.527 (5)	C13—C17	1.548 (5)
C1—H1A	0.9700	C18—H18A	0.9600
C1—H1B	0.9700	C18—H18B	0.9600
C3—O1	1.440 (4)	C18—H18C	0.9600
C3—C2	1.499 (5)	C14—C15	1.514 (5)
C3—C4	1.508 (5)	C14—H14	0.9800
C3—H3	0.9800	C15—C16	1.527 (5)
O1—H1OA	0.821 (11)	C15—H15A	0.9700
O1—H1OB	0.819 (11)	C15—H15B	0.9700
C4—C5	1.499 (5)	C16—C17	1.537 (6)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—C6	1.318 (5)	C17—C20	1.503 (5)
C5—C10	1.527 (5)	C17—H17	0.9800
C6—C7	1.485 (5)	C20—O2	1.222 (4)
C6—H6	0.9300	C20—N1	1.337 (5)
C7—C8	1.517 (5)	N1—C21	1.465 (5)
C7—H7A	0.9700	N1—H1N	0.899 (10)
C7—H7B	0.9700	C21—C23	1.499 (6)
C8—C14	1.513 (4)	C21—C24	1.515 (6)
C8—C9	1.522 (5)	C21—C22	1.518 (6)
C8—H8	0.9800	C22—H22A	0.9600
C9—C11	1.523 (5)	C22—H22B	0.9600
C9—C10	1.552 (4)	C22—H22C	0.9600
C9—H9	0.9800	C23—H23A	0.9600
C10—C19	1.533 (4)	C23—H23B	0.9600
C19—H19A	0.9600	C23—H23C	0.9600
C19—H19B	0.9600	C24—H24A	0.9600
C19—H19C	0.9600	C24—H24B	0.9600
C11—C12	1.527 (4)	C24—H24C	0.9600
C11—H11A	0.9700	O1W—H1W	0.847 (11)
C11—H11B	0.9700	O1W—H2WA	0.850 (11)
C12—C13	1.519 (5)	O1W—H2WB	0.850 (11)
C12—H12A	0.9700	C2—H2A	0.9700
C12—H12B	0.9700	C2—H2B	0.9700
C13—C14	1.517 (5)
C2—C1—C10	114.7 (3)	C14—C13—C17	100.0 (3)
C2—C1—H1A	108.6	C12—C13—C17	115.8 (3)
C10—C1—H1A	108.6	C18—C13—C17	109.5 (3)
C2—C1—H1B	108.6	C13—C18—H18A	109.5
C10—C1—H1B	108.6	C13—C18—H18B	109.5
H1A—C1—H1B	107.6	H18A—C18—H18B	109.5
O1—C3—C2	109.6 (3)	C13—C18—H18C	109.5
O1—C3—C4	111.3 (3)	H18A—C18—H18C	109.5
C2—C3—C4	110.4 (3)	H18B—C18—H18C	109.5
O1—C3—H3	108.5	C8—C14—C15	119.1 (3)
C2—C3—H3	108.5	C8—C14—C13	114.8 (3)
C4—C3—H3	108.5	C15—C14—C13	104.9 (3)
C3—O1—H1OA	110 (7)	C8—C14—H14	105.7
C3—O1—H1OB	92 (7)	C15—C14—H14	105.7
H1OA—O1—H1OB	85 (9)	C13—C14—H14	105.7
C5—C4—C3	112.0 (3)	C14—C15—C16	103.6 (3)
C5—C4—H4A	109.2	C14—C15—H15A	111.0
C3—C4—H4A	109.2	C16—C15—H15A	111.0
C5—C4—H4B	109.2	C14—C15—H15B	111.0
C3—C4—H4B	109.2	C16—C15—H15B	111.0
H4A—C4—H4B	107.9	H15A—C15—H15B	109.0
C6—C5—C4	120.8 (3)	C15—C16—C17	107.0 (3)
C6—C5—C10	122.9 (3)	C15—C16—H16A	110.3
C4—C5—C10	116.2 (3)	C17—C16—H16A	110.3
C5—C6—C7	125.0 (3)	C15—C16—H16B	110.3
C5—C6—H6	117.5	C17—C16—H16B	110.3
C7—C6—H6	117.5	H16A—C16—H16B	108.6
C6—C7—C8	113.4 (3)	C20—C17—C16	113.6 (3)
C6—C7—H7A	108.9	C20—C17—C13	115.0 (3)
C8—C7—H7A	108.9	C16—C17—C13	104.2 (3)
C6—C7—H7B	108.9	C20—C17—H17	107.9
C8—C7—H7B	108.9	C16—C17—H17	107.9
H7A—C7—H7B	107.7	C13—C17—H17	107.9
C14—C8—C7	111.4 (3)	O2—C20—N1	122.6 (4)
C14—C8—C9	109.2 (3)	O2—C20—C17	121.5 (4)
C7—C8—C9	110.2 (2)	N1—C20—C17	115.8 (3)
C14—C8—H8	108.7	C20—N1—C21	126.9 (3)
C7—C8—H8	108.7	C20—N1—H1N	118 (3)
C9—C8—H8	108.7	C21—N1—H1N	115 (3)
C8—C9—C11	112.3 (2)	N1—C21—C23	106.9 (3)
C8—C9—C10	112.9 (3)	N1—C21—C24	109.6 (4)
C11—C9—C10	112.6 (3)	C23—C21—C24	109.7 (4)
C8—C9—H9	106.1	N1—C21—C22	109.7 (3)
C11—C9—H9	106.1	C23—C21—C22	110.2 (5)
C10—C9—H9	106.1	C24—C21—C22	110.6 (4)
C5—C10—C1	108.4 (2)	C21—C22—H22A	109.5
C5—C10—C19	108.2 (3)	C21—C22—H22B	109.5
C1—C10—C19	109.8 (3)	H22A—C22—H22B	109.5
C5—C10—C9	109.9 (3)	C21—C22—H22C	109.5
C1—C10—C9	108.7 (2)	H22A—C22—H22C	109.5
C19—C10—C9	111.8 (2)	H22B—C22—H22C	109.5
C10—C19—H19A	109.5	C21—C23—H23A	109.5
C10—C19—H19B	109.5	C21—C23—H23B	109.5
H19A—C19—H19B	109.5	H23A—C23—H23B	109.5
C10—C19—H19C	109.5	C21—C23—H23C	109.5
H19A—C19—H19C	109.5	H23A—C23—H23C	109.5
H19B—C19—H19C	109.5	H23B—C23—H23C	109.5
C9—C11—C12	114.3 (3)	C21—C24—H24A	109.5
C9—C11—H11A	108.7	C21—C24—H24B	109.5
C12—C11—H11A	108.7	H24A—C24—H24B	109.5
C9—C11—H11B	108.7	C21—C24—H24C	109.5
C12—C11—H11B	108.7	H24A—C24—H24C	109.5
H11A—C11—H11B	107.6	H24B—C24—H24C	109.5
C13—C12—C11	110.7 (3)	H1W—O1W—H2WA	98 (10)
C13—C12—H12A	109.5	H1W—O1W—H2WB	96 (10)
C11—C12—H12A	109.5	H2WA—O1W—H2WB	29 (10)
C13—C12—H12B	109.5	C3—C2—C1	110.1 (3)
C11—C12—H12B	109.5	C3—C2—H2A	109.6
H12A—C12—H12B	108.1	C1—C2—H2A	109.6
C14—C13—C12	107.7 (2)	C3—C2—H2B	109.6
C14—C13—C18	113.1 (3)	C1—C2—H2B	109.6
C12—C13—C18	110.5 (3)	H2A—C2—H2B	108.2
O1—C3—C4—C5	−177.4 (3)	C7—C8—C14—C15	−55.4 (4)
C2—C3—C4—C5	−55.4 (4)	C9—C8—C14—C15	−177.3 (3)
C3—C4—C5—C6	−129.1 (4)	C7—C8—C14—C13	179.1 (3)
C3—C4—C5—C10	51.6 (4)	C9—C8—C14—C13	57.1 (3)
C4—C5—C6—C7	−178.8 (3)	C12—C13—C14—C8	−60.6 (4)
C10—C5—C6—C7	0.5 (5)	C18—C13—C14—C8	61.8 (4)
C5—C6—C7—C8	13.3 (5)	C17—C13—C14—C8	178.2 (3)
C6—C7—C8—C14	−163.2 (3)	C12—C13—C14—C15	166.8 (3)
C6—C7—C8—C9	−41.8 (4)	C18—C13—C14—C15	−70.8 (4)
C14—C8—C9—C11	−49.4 (3)	C17—C13—C14—C15	45.5 (3)
C7—C8—C9—C11	−172.1 (3)	C8—C14—C15—C16	−165.9 (3)
C14—C8—C9—C10	−178.2 (3)	C13—C14—C15—C16	−35.7 (4)
C7—C8—C9—C10	59.2 (3)	C14—C15—C16—C17	11.1 (4)
C6—C5—C10—C1	133.6 (4)	C15—C16—C17—C20	142.5 (3)
C4—C5—C10—C1	−47.1 (4)	C15—C16—C17—C13	16.6 (4)
C6—C5—C10—C19	−107.5 (4)	C14—C13—C17—C20	−162.4 (3)
C4—C5—C10—C19	71.9 (3)	C12—C13—C17—C20	82.3 (4)
C6—C5—C10—C9	14.9 (4)	C18—C13—C17—C20	−43.4 (4)
C4—C5—C10—C9	−165.7 (3)	C14—C13—C17—C16	−37.4 (3)
C2—C1—C10—C5	49.6 (4)	C12—C13—C17—C16	−152.7 (3)
C2—C1—C10—C19	−68.4 (4)	C18—C13—C17—C16	81.6 (4)
C2—C1—C10—C9	169.1 (3)	C16—C17—C20—O2	−26.9 (5)
C8—C9—C10—C5	−44.6 (3)	C13—C17—C20—O2	93.0 (5)
C11—C9—C10—C5	−173.2 (3)	C16—C17—C20—N1	156.3 (3)
C8—C9—C10—C1	−163.0 (3)	C13—C17—C20—N1	−83.7 (4)
C11—C9—C10—C1	68.4 (3)	O2—C20—N1—C21	1.8 (6)
C8—C9—C10—C19	75.7 (3)	C17—C20—N1—C21	178.5 (4)
C11—C9—C10—C19	−52.9 (4)	C20—N1—C21—C23	178.2 (4)
C8—C9—C11—C12	50.1 (4)	C20—N1—C21—C24	59.4 (5)
C10—C9—C11—C12	179.0 (3)	C20—N1—C21—C22	−62.2 (6)
C9—C11—C12—C13	−53.5 (4)	O1—C3—C2—C1	−179.3 (3)
C11—C12—C13—C14	55.9 (4)	C4—C3—C2—C1	57.7 (4)
C11—C12—C13—C18	−68.1 (4)	C10—C1—C2—C3	−57.1 (4)
C11—C12—C13—C17	166.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1OA···O1i	0.82 (1)	1.99 (4)	2.783 (6)	161 (10)
O1W—H1W···O1Wi	0.85 (1)	2.26 (6)	2.798 (9)	121 (6)
O1—H1OB···O1Wii	0.82 (1)	2.31 (9)	2.756 (5)	115 (8)
O1W—H2WA···O1iii	0.85 (1)	1.93 (6)	2.756 (5)	163 (20)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1OA⋯O1i	0.821 (11)	1.99 (4)	2.783 (6)	161 (10)
O1—H1OB⋯O1Wii	0.819 (11)	2.31 (9)	2.756 (5)	115 (8)
O1W—H1W⋯O1Wi	0.847 (11)	2.26 (6)	2.798 (9)	121 (6)
O1W—H2WA⋯O1iii	0.850 (11)	1.93 (6)	2.756 (5)	163 (20)

Symmetry codes: (i) ; (ii) ; (iii) .