Ethyl 3-hydr-oxy-13-methyl-4'-phenyl-2'-(3,4,5-trimethoxy-phen-yl)-6,7,8,9,11,12,13,14,15,16-deca-hydro-spiro-[cyclo-penta-[a]phenanthrene-16,3'-pyrrolidine]-5'-carboxyl-ate.

In the title compound, C(39)H(45)NO(7),the pyrrolidine ring is connected to an estrone group, a trimeth-oxy benzene and a phenyl ring. The pyrrolidine ring exhibits a twist conformation and the other five-membered ring an envelope conformation. Mol-ecules are linked by N-H⋯O hydrogen bonds, C-H⋯π inter-actions and C-H⋯O hydrogen bonds.

Related literature

For general background, see: García-Peláez et al. (2004 ▶); Holland and Roy (1995 ▶); Obniska et al. (2002 ▶); Suzuki et al. (1994 ▶). For bond-length data, see: Allen et al. (1987 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Nardelli (1983 ▶).

Experimental

Crystal data

C39H45NO7

M = 639.76

Monoclinic,

a = 26.1776 (6) Å

b = 10.3379 (2) Å

c = 13.6631 (3) Å

β = 91.1250 (10)°

V = 3696.82 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.30 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.977, T max = 0.981

38566 measured reflections

3462 independent reflections

3186 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.132

S = 1.11

3462 reflections

425 parameters

319 restraints

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034582/bt2805sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034582/bt2805Isup2.hkl

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

C39H45NO7	F(000) = 1368
Mr = 639.76	Dx = 1.149 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 38566 reflections
a = 26.1776 (6) Å	θ = 1.5–30.7°
b = 10.3379 (2) Å	µ = 0.08 mm−1
c = 13.6631 (3) Å	T = 293 K
β = 91.125 (1)°	Prism, colourless
V = 3696.82 (14) Å3	0.30 × 0.30 × 0.25 mm
Z = 4

Bruker KappaAPEXII diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	3186 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and φ scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −31→31
Tmin = 0.977, Tmax = 0.981	k = −12→12
38566 measured reflections	l = −16→15

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.132	w = 1/[σ2(Fo2) + (0.082P)2 + 1.3827P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
3462 reflections	Δρmax = 0.48 e Å−3
425 parameters	Δρmin = −0.24 e Å−3
319 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: 0.0112 (9)

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
C1	0.15174 (10)	0.2439 (3)	0.8431 (2)	0.0417 (6)
H1	0.1599	0.2242	0.9117	0.050*
C2	0.11604 (10)	0.3642 (3)	0.8400 (2)	0.0460 (7)
H2	0.0836	0.3374	0.8093	0.055*
C3	0.17981 (9)	0.3995 (3)	0.7236 (2)	0.0407 (6)
H3	0.1638	0.3548	0.6676	0.049*
C4	0.20146 (9)	0.2927 (3)	0.79377 (18)	0.0367 (6)
C5	0.23722 (10)	0.3500 (3)	0.87263 (18)	0.0380 (6)
C6	0.28956 (10)	0.2904 (3)	0.86410 (19)	0.0400 (6)
C7	0.33546 (11)	0.3760 (4)	0.8831 (2)	0.0569 (8)
H7A	0.3366	0.4019	0.9514	0.068*
H7B	0.3327	0.4535	0.8433	0.068*
C8	0.38453 (11)	0.3024 (4)	0.8583 (2)	0.0591 (9)
H8A	0.4135	0.3602	0.8659	0.071*
H8B	0.3892	0.2317	0.9044	0.071*
C9	0.38342 (10)	0.2479 (3)	0.7540 (2)	0.0459 (7)
H9	0.3827	0.3227	0.7099	0.055*
C10	0.43051 (10)	0.1699 (3)	0.7281 (2)	0.0491 (7)
C11	0.47581 (11)	0.1772 (4)	0.7813 (2)	0.0525 (7)
H11	0.4775	0.2290	0.8369	0.063*
C12	0.51874 (11)	0.1095 (4)	0.7539 (3)	0.0581 (8)
H12	0.5489	0.1171	0.7905	0.070*
C13	0.51690 (11)	0.0307 (4)	0.6726 (2)	0.0568 (8)
C14	0.47166 (13)	0.0182 (5)	0.6216 (3)	0.0717 (11)
H14	0.4699	−0.0366	0.5676	0.086*
C15	0.42859 (12)	0.0850 (5)	0.6485 (2)	0.0669 (10)
C16	0.37936 (15)	0.0587 (8)	0.5916 (3)	0.118 (3)
H16A	0.3851	0.0757	0.5228	0.141*
H16B	0.3711	−0.0323	0.5979	0.141*
C17	0.33571 (11)	0.1342 (4)	0.6219 (2)	0.0580 (9)
H17A	0.3049	0.0859	0.6061	0.070*
H17B	0.3346	0.2135	0.5839	0.070*
C18	0.33529 (10)	0.1692 (3)	0.7300 (2)	0.0398 (6)
H18	0.3360	0.0896	0.7688	0.048*
C19	0.28882 (9)	0.2477 (3)	0.75683 (18)	0.0354 (5)
H19	0.2904	0.3273	0.7180	0.042*
C20	0.23490 (9)	0.1939 (3)	0.7407 (2)	0.0391 (6)
H20A	0.2317	0.1084	0.7692	0.047*
H20B	0.2260	0.1896	0.6715	0.047*
C21	0.21851 (9)	0.4925 (3)	0.68252 (19)	0.0395 (6)
C22	0.23850 (11)	0.5940 (3)	0.7375 (2)	0.0428 (6)
H22	0.2258	0.6113	0.7993	0.051*
C23	0.27723 (12)	0.6695 (3)	0.7007 (2)	0.0466 (7)
C24	0.29617 (11)	0.6431 (3)	0.6073 (2)	0.0482 (7)
C25	0.27614 (11)	0.5418 (3)	0.55345 (19)	0.0450 (7)
C26	0.23668 (10)	0.4680 (3)	0.5897 (2)	0.0423 (6)
H26	0.2224	0.4019	0.5519	0.051*
C27	0.28307 (18)	0.8008 (5)	0.8430 (3)	0.0772 (11)
H27A	0.3020	0.8736	0.8682	0.093*
H27B	0.2883	0.7277	0.8853	0.093*
H27C	0.2474	0.8218	0.8398	0.093*
C28	0.38287 (18)	0.6790 (7)	0.5804 (4)	0.1085 (19)
H28A	0.4057	0.7396	0.5509	0.130*
H28B	0.3864	0.5960	0.5497	0.130*
H28C	0.3911	0.6716	0.6490	0.130*
C29	0.28402 (16)	0.4093 (4)	0.4123 (2)	0.0656 (9)
H29A	0.3019	0.4074	0.3516	0.079*
H29B	0.2479	0.4091	0.3991	0.079*
H29C	0.2931	0.3346	0.4505	0.079*
C30	0.12845 (12)	0.1248 (3)	0.7966 (2)	0.0509 (7)
C31	0.1356 (2)	0.0062 (4)	0.8399 (4)	0.0837 (13)
H31	0.1546	0.0003	0.8979	0.100*
C32	0.1148 (3)	−0.1060 (5)	0.7983 (5)	0.120 (2)
H32	0.1199	−0.1855	0.8288	0.143*
C33	0.0873 (3)	−0.0988 (6)	0.7140 (5)	0.1109 (19)
H33	0.0732	−0.1733	0.6865	0.133*
C34	0.0803 (2)	0.0170 (6)	0.6697 (4)	0.0965 (16)
H34	0.0614	0.0216	0.6113	0.116*
C35	0.10066 (15)	0.1279 (4)	0.7099 (3)	0.0680 (10)
H35	0.0956	0.2065	0.6781	0.082*
C36	0.10410 (11)	0.4229 (4)	0.9382 (3)	0.0603 (9)
C37	0.0691 (2)	0.3797 (8)	1.0936 (4)	0.120 (2)
H37A	0.0974	0.4174	1.1306	0.144*
H37B	0.0430	0.4453	1.0846	0.144*
C38	0.0492 (3)	0.2730 (11)	1.1447 (4)	0.171 (4)
H38A	0.0373	0.3011	1.2072	0.205*
H38B	0.0754	0.2091	1.1541	0.205*
H38C	0.0213	0.2362	1.1075	0.205*
C39	0.28908 (13)	0.1760 (4)	0.9367 (2)	0.0575 (8)
H39A	0.3214	0.1320	0.9354	0.069*
H39B	0.2623	0.1170	0.9183	0.069*
H39C	0.2833	0.2079	1.0015	0.069*
N1	0.13869 (9)	0.4615 (3)	0.7770 (2)	0.0521 (7)
H1A	0.1295	0.5412	0.7721	0.062*
O1	0.22398 (8)	0.4254 (2)	0.93491 (14)	0.0518 (5)
O2	0.55830 (9)	−0.0346 (3)	0.64077 (19)	0.0773 (9)
H2A	0.5829	−0.0194	0.6771	0.093*
O3	0.10751 (10)	0.5359 (3)	0.9562 (2)	0.0814 (9)
O4	0.08664 (12)	0.3347 (3)	0.99822 (19)	0.0842 (9)
O5	0.30005 (10)	0.7705 (2)	0.74826 (17)	0.0641 (7)
O6	0.33211 (10)	0.7226 (3)	0.56819 (18)	0.0708 (7)
O7	0.29758 (9)	0.5228 (3)	0.46488 (15)	0.0590 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0373 (13)	0.0503 (15)	0.0380 (13)	0.0004 (12)	0.0077 (10)	0.0014 (12)
C2	0.0314 (13)	0.0572 (18)	0.0494 (15)	−0.0013 (12)	0.0049 (11)	−0.0071 (14)
C3	0.0294 (12)	0.0489 (15)	0.0438 (13)	0.0008 (11)	0.0005 (10)	0.0030 (13)
C4	0.0330 (12)	0.0394 (13)	0.0379 (12)	0.0011 (11)	0.0033 (10)	−0.0006 (12)
C5	0.0386 (13)	0.0412 (14)	0.0344 (12)	0.0029 (12)	0.0039 (10)	0.0009 (12)
C6	0.0368 (13)	0.0463 (15)	0.0368 (13)	0.0070 (12)	−0.0018 (10)	−0.0014 (12)
C7	0.0415 (15)	0.072 (2)	0.0566 (17)	0.0004 (15)	−0.0050 (13)	−0.0224 (17)
C8	0.0362 (14)	0.079 (2)	0.0620 (18)	−0.0012 (15)	−0.0075 (13)	−0.0192 (18)
C9	0.0325 (13)	0.0553 (17)	0.0498 (15)	0.0026 (13)	−0.0011 (11)	0.0011 (14)
C10	0.0327 (13)	0.0632 (18)	0.0513 (16)	0.0037 (13)	0.0038 (11)	0.0072 (15)
C11	0.0336 (14)	0.0558 (17)	0.0679 (19)	−0.0019 (13)	−0.0018 (12)	0.0006 (16)
C12	0.0305 (13)	0.065 (2)	0.078 (2)	0.0023 (14)	−0.0050 (13)	0.0093 (19)
C13	0.0363 (14)	0.073 (2)	0.0610 (19)	0.0101 (15)	0.0103 (13)	0.0167 (18)
C14	0.0452 (17)	0.112 (3)	0.0578 (19)	0.016 (2)	0.0070 (14)	−0.014 (2)
C15	0.0367 (15)	0.112 (3)	0.0526 (17)	0.0153 (18)	0.0035 (13)	−0.010 (2)
C16	0.050 (2)	0.225 (7)	0.078 (3)	0.037 (3)	−0.0085 (19)	−0.071 (4)
C17	0.0374 (14)	0.085 (2)	0.0515 (17)	0.0059 (16)	0.0002 (12)	−0.0226 (17)
C18	0.0317 (12)	0.0443 (14)	0.0435 (14)	0.0052 (11)	0.0028 (10)	−0.0001 (12)
C19	0.0323 (12)	0.0379 (13)	0.0359 (12)	0.0053 (11)	0.0001 (9)	−0.0016 (11)
C20	0.0327 (13)	0.0430 (15)	0.0416 (14)	0.0025 (11)	0.0021 (10)	−0.0044 (12)
C21	0.0314 (12)	0.0442 (15)	0.0427 (14)	0.0064 (11)	−0.0006 (10)	0.0054 (12)
C22	0.0426 (14)	0.0450 (15)	0.0410 (14)	0.0040 (12)	0.0073 (11)	0.0034 (12)
C23	0.0510 (16)	0.0418 (15)	0.0472 (15)	−0.0010 (13)	0.0031 (12)	0.0018 (13)
C24	0.0482 (16)	0.0516 (17)	0.0449 (15)	−0.0057 (13)	0.0066 (12)	0.0081 (13)
C25	0.0442 (15)	0.0551 (17)	0.0357 (13)	0.0044 (13)	0.0026 (11)	0.0085 (13)
C26	0.0401 (13)	0.0475 (16)	0.0391 (14)	0.0019 (12)	−0.0036 (11)	0.0058 (12)
C27	0.099 (3)	0.070 (2)	0.064 (2)	−0.024 (2)	0.017 (2)	−0.016 (2)
C28	0.061 (3)	0.145 (5)	0.120 (4)	−0.030 (3)	0.023 (3)	−0.018 (4)
C29	0.083 (2)	0.069 (2)	0.0449 (17)	0.002 (2)	0.0097 (15)	−0.0035 (16)
C30	0.0479 (16)	0.0509 (17)	0.0545 (18)	−0.0075 (14)	0.0158 (13)	0.0025 (14)
C31	0.105 (3)	0.060 (2)	0.086 (3)	−0.019 (2)	0.006 (2)	0.017 (2)
C32	0.158 (6)	0.055 (3)	0.146 (5)	−0.036 (3)	0.024 (5)	0.013 (3)
C33	0.135 (5)	0.080 (3)	0.118 (4)	−0.057 (3)	0.017 (4)	−0.015 (3)
C34	0.107 (4)	0.099 (4)	0.083 (3)	−0.052 (3)	0.004 (3)	−0.016 (3)
C35	0.075 (2)	0.065 (2)	0.064 (2)	−0.025 (2)	0.0030 (18)	−0.0038 (18)
C36	0.0352 (14)	0.080 (3)	0.066 (2)	0.0036 (16)	0.0065 (13)	−0.022 (2)
C37	0.121 (4)	0.174 (6)	0.066 (3)	0.014 (4)	0.044 (3)	−0.029 (4)
C38	0.201 (7)	0.237 (10)	0.077 (3)	0.035 (8)	0.069 (4)	0.023 (6)
C39	0.0578 (18)	0.075 (2)	0.0403 (15)	0.0201 (17)	0.0034 (13)	0.0109 (16)
N1	0.0324 (11)	0.0493 (14)	0.0749 (18)	0.0119 (11)	0.0116 (11)	0.0090 (13)
O1	0.0530 (11)	0.0588 (13)	0.0436 (10)	0.0108 (10)	0.0032 (9)	−0.0135 (10)
O2	0.0427 (12)	0.116 (2)	0.0739 (15)	0.0270 (14)	0.0088 (11)	0.0065 (16)
O3	0.0622 (15)	0.080 (2)	0.102 (2)	0.0025 (14)	0.0078 (14)	−0.0431 (18)
O4	0.099 (2)	0.096 (2)	0.0591 (14)	0.0074 (17)	0.0375 (14)	−0.0088 (15)
O5	0.0755 (15)	0.0619 (15)	0.0554 (12)	−0.0238 (13)	0.0129 (11)	−0.0080 (12)
O6	0.0726 (16)	0.0733 (17)	0.0673 (15)	−0.0251 (14)	0.0218 (12)	0.0038 (13)
O7	0.0677 (14)	0.0703 (15)	0.0396 (10)	−0.0097 (12)	0.0127 (9)	0.0016 (11)

C1—C30	1.509 (4)	C20—H20B	0.9700
C1—C2	1.555 (4)	C21—C26	1.386 (4)
C1—C4	1.561 (4)	C21—C22	1.387 (4)
C1—H1	0.9800	C22—C23	1.382 (4)
C2—N1	1.458 (4)	C22—H22	0.9300
C2—C36	1.511 (4)	C23—O5	1.362 (4)
C2—H2	0.9800	C23—C24	1.404 (4)
C3—N1	1.460 (4)	C24—O6	1.366 (4)
C3—C21	1.512 (4)	C24—C25	1.378 (4)
C3—C4	1.562 (4)	C25—O7	1.358 (3)
C3—H3	0.9800	C25—C26	1.384 (4)
C4—C5	1.533 (4)	C26—H26	0.9300
C4—C20	1.536 (4)	C27—O5	1.411 (4)
C5—O1	1.210 (3)	C27—H27A	0.9600
C5—C6	1.509 (4)	C27—H27B	0.9600
C6—C7	1.511 (4)	C27—H27C	0.9600
C6—C19	1.530 (4)	C28—O6	1.410 (6)
C6—C39	1.544 (5)	C28—H28A	0.9600
C7—C8	1.537 (5)	C28—H28B	0.9600
C7—H7A	0.9700	C28—H28C	0.9600
C7—H7B	0.9700	C29—O7	1.417 (5)
C8—C9	1.532 (4)	C29—H29A	0.9600
C8—H8A	0.9700	C29—H29B	0.9600
C8—H8B	0.9700	C29—H29C	0.9600
C9—C10	1.521 (4)	C30—C31	1.373 (6)
C9—C18	1.530 (4)	C30—C35	1.378 (5)
C9—H9	0.9800	C31—C32	1.396 (7)
C10—C11	1.380 (4)	C31—H31	0.9300
C10—C15	1.399 (5)	C32—C33	1.348 (9)
C11—C12	1.382 (5)	C32—H32	0.9300
C11—H11	0.9300	C33—C34	1.353 (9)
C12—C13	1.378 (5)	C33—H33	0.9300
C12—H12	0.9300	C34—C35	1.376 (6)
C13—O2	1.356 (4)	C34—H34	0.9300
C13—C14	1.369 (5)	C35—H35	0.9300
C14—C15	1.378 (5)	C36—O3	1.197 (5)
C14—H14	0.9300	C36—O4	1.314 (5)
C15—C16	1.516 (5)	C37—C38	1.411 (12)
C16—C17	1.450 (5)	C37—O4	1.466 (5)
C16—H16A	0.9700	C37—H37A	0.9700
C16—H16B	0.9700	C37—H37B	0.9700
C17—C18	1.522 (4)	C38—H38A	0.9600
C17—H17A	0.9700	C38—H38B	0.9600
C17—H17B	0.9700	C38—H38C	0.9600
C18—C19	1.513 (4)	C39—H39A	0.9600
C18—H18	0.9800	C39—H39B	0.9600
C19—C20	1.529 (4)	C39—H39C	0.9600
C19—H19	0.9800	N1—H1A	0.8600
C20—H20A	0.9700	O2—H2A	0.8200
C30—C1—C2	113.8 (2)	C20—C19—H19	106.0
C30—C1—C4	114.6 (2)	C6—C19—H19	106.0
C2—C1—C4	103.7 (2)	C19—C20—C4	102.9 (2)
C30—C1—H1	108.2	C19—C20—H20A	111.2
C2—C1—H1	108.2	C4—C20—H20A	111.2
C4—C1—H1	108.2	C19—C20—H20B	111.2
N1—C2—C36	109.9 (3)	C4—C20—H20B	111.2
N1—C2—C1	108.4 (2)	H20A—C20—H20B	109.1
C36—C2—C1	115.6 (3)	C26—C21—C22	120.1 (3)
N1—C2—H2	107.5	C26—C21—C3	117.8 (3)
C36—C2—H2	107.5	C22—C21—C3	121.9 (2)
C1—C2—H2	107.5	C23—C22—C21	120.1 (3)
N1—C3—C21	114.3 (2)	C23—C22—H22	120.0
N1—C3—C4	105.4 (2)	C21—C22—H22	120.0
C21—C3—C4	116.1 (2)	O5—C23—C22	125.2 (3)
N1—C3—H3	106.8	O5—C23—C24	115.0 (3)
C21—C3—H3	106.8	C22—C23—C24	119.7 (3)
C4—C3—H3	106.8	O6—C24—C25	120.4 (3)
C5—C4—C20	104.1 (2)	O6—C24—C23	119.8 (3)
C5—C4—C1	108.9 (2)	C25—C24—C23	119.7 (3)
C20—C4—C1	118.5 (2)	O7—C25—C24	115.2 (3)
C5—C4—C3	111.5 (2)	O7—C25—C26	124.3 (3)
C20—C4—C3	112.6 (2)	C24—C25—C26	120.5 (3)
C1—C4—C3	101.4 (2)	C25—C26—C21	119.9 (3)
O1—C5—C6	126.2 (2)	C25—C26—H26	120.1
O1—C5—C4	124.4 (2)	C21—C26—H26	120.1
C6—C5—C4	109.3 (2)	O5—C27—H27A	109.5
C5—C6—C7	117.9 (3)	O5—C27—H27B	109.5
C5—C6—C19	101.4 (2)	H27A—C27—H27B	109.5
C7—C6—C19	109.2 (2)	O5—C27—H27C	109.5
C5—C6—C39	104.1 (2)	H27A—C27—H27C	109.5
C7—C6—C39	110.8 (3)	H27B—C27—H27C	109.5
C19—C6—C39	113.2 (3)	O6—C28—H28A	109.5
C6—C7—C8	109.7 (3)	O6—C28—H28B	109.5
C6—C7—H7A	109.7	H28A—C28—H28B	109.5
C8—C7—H7A	109.7	O6—C28—H28C	109.5
C6—C7—H7B	109.7	H28A—C28—H28C	109.5
C8—C7—H7B	109.7	H28B—C28—H28C	109.5
H7A—C7—H7B	108.2	O7—C29—H29A	109.5
C9—C8—C7	112.7 (2)	O7—C29—H29B	109.5
C9—C8—H8A	109.0	H29A—C29—H29B	109.5
C7—C8—H8A	109.0	O7—C29—H29C	109.5
C9—C8—H8B	109.0	H29A—C29—H29C	109.5
C7—C8—H8B	109.0	H29B—C29—H29C	109.5
H8A—C8—H8B	107.8	C31—C30—C35	117.1 (4)
C10—C9—C18	109.6 (3)	C31—C30—C1	119.9 (3)
C10—C9—C8	114.2 (2)	C35—C30—C1	123.0 (3)
C18—C9—C8	113.3 (2)	C30—C31—C32	121.2 (5)
C10—C9—H9	106.4	C30—C31—H31	119.4
C18—C9—H9	106.4	C32—C31—H31	119.4
C8—C9—H9	106.4	C33—C32—C31	119.9 (5)
C11—C10—C15	117.4 (3)	C33—C32—H32	120.0
C11—C10—C9	122.8 (3)	C31—C32—H32	120.0
C15—C10—C9	119.8 (2)	C32—C33—C34	119.8 (5)
C10—C11—C12	121.7 (3)	C32—C33—H33	120.1
C10—C11—H11	119.2	C34—C33—H33	120.1
C12—C11—H11	119.2	C33—C34—C35	120.7 (5)
C13—C12—C11	120.1 (3)	C33—C34—H34	119.7
C13—C12—H12	119.9	C35—C34—H34	119.7
C11—C12—H12	119.9	C34—C35—C30	121.2 (4)
O2—C13—C14	118.6 (3)	C34—C35—H35	119.4
O2—C13—C12	122.5 (3)	C30—C35—H35	119.4
C14—C13—C12	118.9 (3)	O3—C36—O4	125.1 (4)
C13—C14—C15	121.4 (4)	O3—C36—C2	124.0 (4)
C13—C14—H14	119.3	O4—C36—C2	110.8 (3)
C15—C14—H14	119.3	C38—C37—O4	108.5 (6)
C14—C15—C10	120.3 (3)	C38—C37—H37A	110.0
C14—C15—C16	117.7 (4)	O4—C37—H37A	110.0
C10—C15—C16	121.9 (3)	C38—C37—H37B	110.0
C17—C16—C15	115.1 (4)	O4—C37—H37B	110.0
C17—C16—H16A	108.5	H37A—C37—H37B	108.4
C15—C16—H16A	108.5	C37—C38—H38A	109.5
C17—C16—H16B	108.5	C37—C38—H38B	109.5
C15—C16—H16B	108.5	H38A—C38—H38B	109.5
H16A—C16—H16B	107.5	C37—C38—H38C	109.5
C16—C17—C18	115.2 (3)	H38A—C38—H38C	109.5
C16—C17—H17A	108.5	H38B—C38—H38C	109.5
C18—C17—H17A	108.5	C6—C39—H39A	109.5
C16—C17—H17B	108.5	C6—C39—H39B	109.5
C18—C17—H17B	108.5	H39A—C39—H39B	109.5
H17A—C17—H17B	107.5	C6—C39—H39C	109.5
C19—C18—C17	112.6 (2)	H39A—C39—H39C	109.5
C19—C18—C9	109.0 (2)	H39B—C39—H39C	109.5
C17—C18—C9	108.3 (2)	C2—N1—C3	107.7 (2)
C19—C18—H18	109.0	C2—N1—H1A	126.1
C17—C18—H18	109.0	C3—N1—H1A	126.1
C9—C18—H18	109.0	C13—O2—H2A	109.5
C18—C19—C20	120.9 (2)	C36—O4—C37	117.0 (4)
C18—C19—C6	113.0 (2)	C23—O5—C27	117.7 (3)
C20—C19—C6	103.7 (2)	C24—O6—C28	114.6 (4)
C18—C19—H19	106.0	C25—O7—C29	117.9 (3)
C30—C1—C2—N1	−114.0 (3)	C17—C18—C19—C6	−176.6 (3)
C4—C1—C2—N1	11.1 (3)	C9—C18—C19—C6	−56.4 (3)
C30—C1—C2—C36	122.1 (3)	C5—C6—C19—C18	−173.3 (2)
C4—C1—C2—C36	−112.8 (3)	C7—C6—C19—C18	61.6 (3)
C30—C1—C4—C5	−145.9 (3)	C39—C6—C19—C18	−62.3 (3)
C2—C1—C4—C5	89.5 (3)	C5—C6—C19—C20	−40.5 (3)
C30—C1—C4—C20	−27.4 (3)	C7—C6—C19—C20	−165.6 (2)
C2—C1—C4—C20	−151.9 (2)	C39—C6—C19—C20	70.4 (3)
C30—C1—C4—C3	96.3 (3)	C18—C19—C20—C4	170.4 (2)
C2—C1—C4—C3	−28.3 (3)	C6—C19—C20—C4	42.3 (3)
N1—C3—C4—C5	−78.9 (3)	C5—C4—C20—C19	−26.6 (3)
C21—C3—C4—C5	48.7 (3)	C1—C4—C20—C19	−147.7 (2)
N1—C3—C4—C20	164.5 (2)	C3—C4—C20—C19	94.4 (2)
C21—C3—C4—C20	−67.8 (3)	N1—C3—C21—C26	−139.7 (3)
N1—C3—C4—C1	36.9 (3)	C4—C3—C21—C26	97.2 (3)
C21—C3—C4—C1	164.6 (2)	N1—C3—C21—C22	45.1 (3)
C20—C4—C5—O1	−174.4 (3)	C4—C3—C21—C22	−78.0 (3)
C1—C4—C5—O1	−47.1 (4)	C26—C21—C22—C23	−1.1 (4)
C3—C4—C5—O1	64.0 (3)	C3—C21—C22—C23	174.0 (3)
C20—C4—C5—C6	1.6 (3)	C21—C22—C23—O5	−179.3 (3)
C1—C4—C5—C6	128.9 (2)	C21—C22—C23—C24	0.1 (4)
C3—C4—C5—C6	−120.0 (2)	O5—C23—C24—O6	−4.7 (4)
O1—C5—C6—C7	−41.2 (4)	C22—C23—C24—O6	175.8 (3)
C4—C5—C6—C7	142.9 (3)	O5—C23—C24—C25	179.2 (3)
O1—C5—C6—C19	−160.2 (3)	C22—C23—C24—C25	−0.3 (4)
C4—C5—C6—C19	23.9 (3)	O6—C24—C25—O7	5.0 (4)
O1—C5—C6—C39	82.0 (4)	C23—C24—C25—O7	−178.9 (3)
C4—C5—C6—C39	−93.9 (3)	O6—C24—C25—C26	−174.5 (3)
C5—C6—C7—C8	−173.0 (3)	C23—C24—C25—C26	1.6 (4)
C19—C6—C7—C8	−58.1 (3)	O7—C25—C26—C21	177.9 (3)
C39—C6—C7—C8	67.3 (3)	C24—C25—C26—C21	−2.6 (4)
C6—C7—C8—C9	54.4 (4)	C22—C21—C26—C25	2.4 (4)
C7—C8—C9—C10	−177.8 (3)	C3—C21—C26—C25	−172.9 (2)
C7—C8—C9—C18	−51.3 (4)	C2—C1—C30—C31	−139.2 (4)
C18—C9—C10—C11	−145.8 (3)	C4—C1—C30—C31	101.7 (4)
C8—C9—C10—C11	−17.4 (5)	C2—C1—C30—C35	42.2 (4)
C18—C9—C10—C15	33.1 (4)	C4—C1—C30—C35	−76.8 (4)
C8—C9—C10—C15	161.5 (3)	C35—C30—C31—C32	−1.0 (7)
C15—C10—C11—C12	3.8 (5)	C1—C30—C31—C32	−179.6 (5)
C9—C10—C11—C12	−177.2 (3)	C30—C31—C32—C33	0.2 (10)
C10—C11—C12—C13	−1.0 (5)	C31—C32—C33—C34	0.4 (11)
C11—C12—C13—O2	177.8 (3)	C32—C33—C34—C35	−0.3 (10)
C11—C12—C13—C14	−1.8 (6)	C33—C34—C35—C30	−0.4 (8)
O2—C13—C14—C15	−178.0 (4)	C31—C30—C35—C34	1.1 (6)
C12—C13—C14—C15	1.6 (6)	C1—C30—C35—C34	179.6 (4)
C13—C14—C15—C10	1.3 (7)	N1—C2—C36—O3	7.9 (4)
C13—C14—C15—C16	−176.3 (5)	C1—C2—C36—O3	131.0 (4)
C11—C10—C15—C14	−4.0 (6)	N1—C2—C36—O4	−176.0 (3)
C9—C10—C15—C14	177.0 (4)	C1—C2—C36—O4	−52.9 (4)
C11—C10—C15—C16	173.5 (5)	C36—C2—N1—C3	139.8 (2)
C9—C10—C15—C16	−5.5 (6)	C1—C2—N1—C3	12.5 (3)
C14—C15—C16—C17	−178.6 (5)	C21—C3—N1—C2	−160.0 (2)
C10—C15—C16—C17	3.8 (8)	C4—C3—N1—C2	−31.3 (3)
C15—C16—C17—C18	−31.5 (7)	O3—C36—O4—C37	1.3 (6)
C16—C17—C18—C19	−179.9 (4)	C2—C36—O4—C37	−174.8 (4)
C16—C17—C18—C9	59.5 (5)	C38—C37—O4—C36	176.6 (5)
C10—C9—C18—C19	179.6 (2)	C22—C23—O5—C27	0.2 (5)
C8—C9—C18—C19	50.7 (3)	C24—C23—O5—C27	−179.3 (3)
C10—C9—C18—C17	−57.6 (3)	C25—C24—O6—C28	−86.9 (4)
C8—C9—C18—C17	173.5 (3)	C23—C24—O6—C28	97.0 (4)
C17—C18—C19—C20	59.7 (4)	C24—C25—O7—C29	170.9 (3)
C9—C18—C19—C20	179.8 (2)	C26—C25—O7—C29	−9.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1i	0.82	1.99	2.782 (4)	163
C39—H39A···O3ii	0.96	2.56	3.378 (4)	144
C29—H29A···Cg1iii	0.96	3.00	3.820 (4)	144
C1—H1···O4	0.98	2.54	2.901 (4)	101

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1i	0.82	1.99	2.782 (4)	163
C39—H39A⋯O3ii	0.96	2.56	3.378 (4)	144
C29—H29A⋯Cg1iii	0.96	3.00	3.820 (4)	144

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