Ethyl 1'-[1-(4-methoxyphenyl)-3-phenoxy-4-phenylazetidin-1-yl]-1,3-dioxo-2',3',5',6',7',7a'-hexahydroindan-2-spiro-3'-1'H-pyrrolizine-2'-carboxylate.

In the title compound, C(34)H(32)N(2)O(7), the methyl group and methylene H atoms of the ethoxycarbonyl substituent are disordered over two positions with site occupancy factors for the major and minor conformers of 0.594 (8) and 0.406 (8), respectively. The unsubstituted ring of the pyrrolizine ring system exhibits a twist conformation, the other an envelope conformation. In the crystal structure, mol-ecules are linked through C-H⋯O hydrogen bonds; intramolecular C-H⋯O interactions are also observed.

Related literature

For related literature, see: Allen et al. (1987 ▶); Alonso et al. (2002 ▶); Aoyama et al. (2001 ▶); Chande et al. (2005 ▶); Cremer & Pople (1975 ▶); Escolano & Jones (2000 ▶); Halve et al. (2007 ▶); Kamala et al. (2008 ▶); Nardelli (1983 ▶); Pinna et al. (2002 ▶); Poornachandran & Raghunathan (2006 ▶); Raj & Raghunathan (2001 ▶); Raj et al. (2003 ▶).

Experimental

Crystal data

C34H32N2O7

M = 580.62

Monoclinic,

a = 12.4776 (7) Å

b = 12.4946 (6) Å

c = 19.4958 (11) Å

β = 106.013 (3)°

V = 2921.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.973, T max = 0.982

66713 measured reflections

7446 independent reflections

4654 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.225

S = 0.92

7446 reflections

395 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.25 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: SHELXS86 (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/S1600536808026913/bt2772sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026913/bt2772Isup2.hkl

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

C34H32N2O7	F000 = 1224
Mr = 580.62	Dx = 1.320 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 66713 reflections
a = 12.4776 (7) Å	θ = 2.0–28.7º
b = 12.4946 (6) Å	µ = 0.09 mm−1
c = 19.4958 (11) Å	T = 293 (2) K
β = 106.013 (3)º	Prism, colourless
V = 2921.5 (3) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker Kappa APEXII diffractometer	7446 independent reflections
Radiation source: fine-focus sealed tube	4654 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.037
T = 293(2) K	θmax = 28.7º
ω and φ scan	θmin = 2.0º
Absorption correction: multi-scan(Blessing, 1995)	h = −16→16
Tmin = 0.973, Tmax = 0.982	k = −16→16
66713 measured reflections	l = −26→26

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)] = 0.057	H-atom parameters constrained
wR(F2) = 0.225	w = 1/[σ2(Fo2) + (0.1376P)2 + 1.4238P] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
7446 reflections	Δρmax = 0.70 e Å−3
395 parameters	Δρmin = −0.25 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.10567 (17)	0.74081 (19)	0.12572 (12)	0.0482 (5)
C2	0.20897 (17)	0.67935 (17)	0.16633 (12)	0.0457 (5)
H2	0.1884	0.6121	0.1852	0.055*
C3	0.22628 (15)	0.76987 (17)	0.22302 (11)	0.0414 (4)
H3	0.2171	0.7419	0.2680	0.050*
C4	0.32801 (15)	0.84224 (16)	0.23708 (10)	0.0386 (4)
H4	0.3175	0.9013	0.2676	0.046*
C5	0.43512 (16)	0.78329 (19)	0.27532 (11)	0.0456 (5)
H5	0.4292	0.7084	0.2598	0.055*
C6	0.4746 (2)	0.7876 (3)	0.35635 (13)	0.0686 (8)
H6A	0.4487	0.7259	0.3775	0.082*
H6B	0.4493	0.8524	0.3745	0.082*
C7	0.6006 (3)	0.7866 (3)	0.37091 (16)	0.0828 (9)
H7A	0.6364	0.8171	0.4173	0.099*
H7B	0.6280	0.7143	0.3691	0.099*
C8	0.6216 (2)	0.8539 (3)	0.31244 (15)	0.0715 (8)
H8A	0.6283	0.9288	0.3259	0.086*
H8B	0.6893	0.8315	0.3013	0.086*
C9	0.48118 (15)	0.91979 (17)	0.20062 (11)	0.0413 (4)
C10	0.35503 (15)	0.88984 (16)	0.17155 (10)	0.0383 (4)
H10	0.3473	0.8337	0.1354	0.046*
C11	0.49581 (16)	1.03640 (19)	0.22699 (12)	0.0470 (5)
C12	0.53156 (17)	1.10040 (19)	0.17360 (12)	0.0493 (5)
C13	0.5449 (2)	1.2101 (2)	0.17030 (17)	0.0686 (7)
H13	0.5286	1.2553	0.2040	0.082*
C14	0.5828 (3)	1.2501 (3)	0.11582 (19)	0.0835 (9)
H14	0.5923	1.3235	0.1126	0.100*
C15	0.6071 (3)	1.1836 (3)	0.06565 (17)	0.0780 (9)
H15	0.6333	1.2131	0.0296	0.094*
C16	0.5934 (2)	1.0753 (2)	0.06794 (14)	0.0607 (6)
H16	0.6095	1.0307	0.0339	0.073*
C17	0.55463 (16)	1.03373 (19)	0.12275 (11)	0.0468 (5)
C18	0.53427 (16)	0.92134 (18)	0.13783 (11)	0.0443 (5)
C19	0.28198 (16)	0.98272 (18)	0.13906 (11)	0.0425 (4)
C20	0.1937 (3)	1.0703 (3)	0.03029 (16)	0.0873 (10)
H20A	0.1358	1.0866	0.0532	0.105*	0.594 (8)
H20B	0.1582	1.0475	−0.0182	0.105*	0.594 (8)
H20C	0.2032	1.1346	0.0593	0.105*	0.406 (8)
H20D	0.2132	1.0867	−0.0134	0.105*	0.406 (8)
C21A	0.2620 (3)	1.1658 (3)	0.02972 (16)	0.107 (3)	0.594 (8)
H21A	0.2156	1.2225	0.0044	0.161*	0.594 (8)
H21B	0.3185	1.1494	0.0065	0.161*	0.594 (8)
H21C	0.2966	1.1881	0.0779	0.161*	0.594 (8)
C21B	0.0759 (8)	1.0331 (10)	0.0133 (6)	0.122 (5)	0.406 (8)
H21D	0.0275	1.0881	−0.0123	0.184*	0.406 (8)
H21E	0.0571	1.0175	0.0568	0.184*	0.406 (8)
H21F	0.0672	0.9697	−0.0155	0.184*	0.406 (8)
C22	0.27365 (19)	0.58488 (18)	0.08017 (12)	0.0491 (5)
C23	0.3552 (2)	0.5747 (2)	0.04537 (14)	0.0640 (7)
H23	0.4182	0.6181	0.0576	0.077*
C24	0.3422 (3)	0.4997 (4)	−0.00750 (19)	0.0970 (12)
H24	0.3968	0.4920	−0.0314	0.116*
C25	0.2488 (4)	0.4355 (4)	−0.0256 (2)	0.1091 (14)
H25	0.2407	0.3848	−0.0616	0.131*
C26	0.1680 (3)	0.4462 (3)	0.00915 (19)	0.0888 (10)
H26	0.1052	0.4025	−0.0030	0.107*
C27	0.1798 (2)	0.5210 (2)	0.06166 (15)	0.0627 (6)
H27	0.1246	0.5290	0.0850	0.075*
C28	0.03902 (16)	0.87881 (18)	0.19790 (11)	0.0432 (5)
C29	−0.07248 (19)	0.8653 (2)	0.16113 (14)	0.0612 (7)
H29	−0.0927	0.8169	0.1235	0.073*
C30	−0.1525 (2)	0.9233 (3)	0.18030 (15)	0.0716 (8)
H30	−0.2271	0.9139	0.1557	0.086*
C31	−0.12380 (17)	0.9960 (2)	0.23592 (13)	0.0521 (5)
C32	−0.01383 (18)	1.0081 (2)	0.27267 (13)	0.0539 (6)
H32	0.0064	1.0560	0.3105	0.065*
C33	0.06725 (17)	0.9490 (2)	0.25347 (13)	0.0541 (6)
H33	0.1417	0.9573	0.2788	0.065*
C34	−0.1843 (2)	1.1296 (3)	0.30349 (17)	0.0733 (8)
H34A	−0.2519	1.1612	0.3083	0.110*
H34B	−0.1390	1.1839	0.2905	0.110*
H34C	−0.1442	1.0979	0.3480	0.110*
N1	0.11960 (13)	0.81469 (15)	0.17864 (9)	0.0434 (4)
N2	0.52356 (13)	0.83599 (16)	0.25133 (9)	0.0475 (4)
O1	0.03516 (15)	0.73016 (17)	0.06980 (10)	0.0708 (5)
O2	0.29362 (12)	0.66240 (13)	0.13240 (9)	0.0511 (4)
O3	0.26535 (15)	0.98497 (17)	0.06915 (9)	0.0666 (5)
O4	0.24443 (15)	1.04707 (14)	0.17193 (10)	0.0616 (5)
O5	0.55371 (16)	0.84351 (15)	0.10714 (10)	0.0639 (5)
O6	0.48258 (15)	1.06910 (16)	0.28235 (10)	0.0658 (5)
O7	−0.21005 (14)	1.05041 (18)	0.25026 (11)	0.0750 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0365 (10)	0.0494 (12)	0.0561 (12)	−0.0029 (9)	0.0085 (9)	−0.0051 (10)
C2	0.0376 (10)	0.0395 (11)	0.0607 (12)	−0.0051 (8)	0.0145 (9)	−0.0032 (9)
C3	0.0311 (9)	0.0451 (11)	0.0476 (10)	−0.0006 (8)	0.0102 (8)	0.0025 (9)
C4	0.0309 (8)	0.0410 (11)	0.0427 (10)	−0.0004 (7)	0.0084 (7)	−0.0009 (8)
C5	0.0338 (9)	0.0499 (12)	0.0512 (11)	0.0008 (8)	0.0083 (8)	0.0021 (9)
C6	0.0541 (14)	0.101 (2)	0.0501 (13)	0.0124 (14)	0.0131 (11)	0.0156 (14)
C7	0.0630 (17)	0.109 (3)	0.0643 (17)	−0.0003 (17)	−0.0024 (13)	0.0053 (17)
C8	0.0395 (12)	0.100 (2)	0.0647 (15)	−0.0042 (13)	−0.0028 (11)	0.0059 (15)
C9	0.0309 (9)	0.0485 (12)	0.0448 (10)	−0.0033 (8)	0.0109 (7)	−0.0059 (9)
C10	0.0308 (8)	0.0401 (10)	0.0425 (10)	−0.0036 (7)	0.0077 (7)	−0.0026 (8)
C11	0.0322 (9)	0.0539 (13)	0.0558 (12)	−0.0035 (9)	0.0135 (8)	−0.0120 (10)
C12	0.0351 (10)	0.0510 (13)	0.0590 (13)	−0.0064 (9)	0.0085 (9)	−0.0057 (10)
C13	0.0658 (16)	0.0542 (15)	0.0807 (18)	−0.0097 (12)	0.0118 (14)	−0.0094 (13)
C14	0.089 (2)	0.0647 (18)	0.090 (2)	−0.0250 (16)	0.0134 (18)	0.0087 (17)
C15	0.0711 (18)	0.087 (2)	0.0725 (18)	−0.0257 (16)	0.0138 (14)	0.0177 (17)
C16	0.0476 (12)	0.0776 (18)	0.0566 (13)	−0.0120 (12)	0.0137 (10)	0.0049 (12)
C17	0.0311 (9)	0.0563 (13)	0.0512 (11)	−0.0050 (9)	0.0086 (8)	0.0012 (10)
C18	0.0327 (9)	0.0529 (12)	0.0485 (11)	0.0011 (8)	0.0131 (8)	−0.0045 (9)
C19	0.0340 (9)	0.0434 (11)	0.0495 (11)	−0.0026 (8)	0.0105 (8)	0.0019 (9)
C20	0.088 (2)	0.098 (3)	0.0670 (17)	0.0316 (19)	0.0052 (15)	0.0254 (17)
C21A	0.133 (6)	0.068 (4)	0.107 (5)	0.023 (4)	0.011 (4)	0.022 (3)
C21B	0.080 (6)	0.141 (10)	0.129 (9)	0.019 (6)	0.001 (6)	0.055 (8)
C22	0.0487 (11)	0.0448 (12)	0.0528 (12)	−0.0033 (9)	0.0123 (9)	−0.0031 (10)
C23	0.0611 (14)	0.0724 (18)	0.0618 (14)	−0.0109 (13)	0.0226 (12)	−0.0083 (13)
C24	0.100 (2)	0.118 (3)	0.089 (2)	−0.022 (2)	0.053 (2)	−0.040 (2)
C25	0.130 (3)	0.118 (3)	0.094 (2)	−0.044 (3)	0.054 (2)	−0.059 (2)
C26	0.091 (2)	0.086 (2)	0.094 (2)	−0.0354 (18)	0.0343 (19)	−0.0377 (19)
C27	0.0583 (14)	0.0573 (15)	0.0752 (16)	−0.0134 (12)	0.0231 (12)	−0.0146 (13)
C28	0.0328 (9)	0.0461 (11)	0.0500 (11)	0.0008 (8)	0.0103 (8)	0.0046 (9)
C29	0.0388 (11)	0.0800 (18)	0.0580 (13)	0.0066 (11)	0.0023 (10)	−0.0167 (12)
C30	0.0341 (11)	0.100 (2)	0.0713 (16)	0.0126 (12)	−0.0011 (11)	−0.0178 (15)
C31	0.0366 (10)	0.0601 (14)	0.0599 (13)	0.0074 (9)	0.0137 (9)	0.0025 (11)
C32	0.0401 (11)	0.0583 (14)	0.0641 (14)	−0.0066 (10)	0.0155 (10)	−0.0128 (11)
C33	0.0306 (9)	0.0584 (14)	0.0709 (15)	−0.0067 (9)	0.0098 (9)	−0.0141 (12)
C34	0.0636 (16)	0.082 (2)	0.0797 (19)	0.0160 (14)	0.0285 (14)	−0.0077 (15)
N1	0.0304 (8)	0.0476 (10)	0.0494 (9)	−0.0001 (7)	0.0061 (7)	−0.0033 (8)
N2	0.0293 (8)	0.0623 (12)	0.0488 (10)	0.0019 (7)	0.0073 (7)	0.0034 (8)
O1	0.0556 (10)	0.0786 (13)	0.0656 (11)	0.0073 (9)	−0.0046 (8)	−0.0213 (10)
O2	0.0393 (7)	0.0479 (9)	0.0687 (10)	−0.0074 (6)	0.0192 (7)	−0.0137 (7)
O3	0.0678 (11)	0.0783 (13)	0.0503 (9)	0.0240 (9)	0.0105 (8)	0.0119 (9)
O4	0.0674 (11)	0.0517 (10)	0.0673 (11)	0.0153 (8)	0.0215 (9)	0.0030 (8)
O5	0.0721 (11)	0.0602 (11)	0.0690 (11)	0.0061 (9)	0.0357 (9)	−0.0104 (9)
O6	0.0601 (10)	0.0743 (12)	0.0706 (11)	−0.0127 (9)	0.0307 (9)	−0.0277 (9)
O7	0.0414 (9)	0.0941 (15)	0.0896 (13)	0.0143 (9)	0.0183 (9)	−0.0205 (11)

C1—O1	1.205 (3)	C19—O4	1.201 (3)
C1—N1	1.359 (3)	C19—O3	1.321 (3)
C1—C2	1.522 (3)	C20—C21B	1.489 (11)
C2—O2	1.408 (2)	C20—O3	1.462 (3)
C2—C3	1.554 (3)	C20—C21A	1.4690
C2—H2	0.9800	C20—H20A	0.9700
C3—N1	1.483 (3)	C20—H20B	0.9700
C3—C4	1.521 (3)	C20—H20C	0.9700
C3—H3	0.9800	C20—H20D	0.9700
C4—C10	1.529 (3)	C21A—H21A	0.9600
C4—C5	1.528 (3)	C21A—H21B	0.9600
C4—H4	0.9800	C21A—H21C	0.9600
C5—N2	1.468 (3)	C21B—H21D	0.9600
C5—C6	1.520 (3)	C21B—H21E	0.9600
C5—H5	0.9800	C21B—H21F	0.9600
C6—C7	1.519 (4)	C22—C23	1.376 (3)
C6—H6A	0.9700	C22—O2	1.377 (3)
C6—H6B	0.9700	C22—C27	1.380 (3)
C7—C8	1.497 (4)	C23—C24	1.369 (4)
C7—H7A	0.9700	C23—H23	0.9300
C7—H7B	0.9700	C24—C25	1.378 (5)
C8—N2	1.470 (3)	C24—H24	0.9300
C8—H8A	0.9700	C25—C26	1.368 (5)
C8—H8B	0.9700	C25—H25	0.9300
C9—N2	1.437 (3)	C26—C27	1.364 (4)
C9—C11	1.539 (3)	C26—H26	0.9300
C9—C18	1.544 (3)	C27—H27	0.9300
C9—C10	1.564 (3)	C28—C33	1.363 (3)
C10—C19	1.503 (3)	C28—C29	1.388 (3)
C10—H10	0.9800	C28—N1	1.415 (3)
C11—O6	1.207 (3)	C29—C30	1.366 (4)
C11—C12	1.476 (3)	C29—H29	0.9300
C12—C13	1.385 (4)	C30—C31	1.384 (4)
C12—C17	1.385 (3)	C30—H30	0.9300
C13—C14	1.370 (5)	C31—O7	1.365 (3)
C13—H13	0.9300	C31—C32	1.370 (3)
C14—C15	1.379 (5)	C32—C33	1.385 (3)
C14—H14	0.9300	C32—H32	0.9300
C15—C16	1.367 (4)	C33—H33	0.9300
C15—H15	0.9300	C34—O7	1.405 (4)
C16—C17	1.389 (3)	C34—H34A	0.9600
C16—H16	0.9300	C34—H34B	0.9600
C17—C18	1.471 (3)	C34—H34C	0.9600
C18—O5	1.201 (3)
O1—C1—N1	132.1 (2)	C21B—C20—O3	108.2 (5)
O1—C1—C2	135.9 (2)	C21B—C20—C21A	142.3 (5)
N1—C1—C2	92.01 (17)	O3—C20—C21A	108.85 (17)
O2—C2—C1	117.96 (19)	C21B—C20—H20A	49.7
O2—C2—C3	117.93 (16)	O3—C20—H20A	109.9
C1—C2—C3	86.24 (16)	C21A—C20—H20A	109.9
O2—C2—H2	110.9	C21B—C20—H20B	62.3
C1—C2—H2	110.9	O3—C20—H20B	109.9
C3—C2—H2	110.9	C21A—C20—H20B	109.9
N1—C3—C4	116.81 (17)	H20A—C20—H20B	108.3
N1—C3—C2	86.19 (15)	C21B—C20—H20C	110.1
C4—C3—C2	120.41 (17)	O3—C20—H20C	110.1
N1—C3—H3	110.4	C21A—C20—H20C	49.7
C4—C3—H3	110.4	H20A—C20—H20C	62.9
C2—C3—H3	110.4	H20B—C20—H20C	139.5
C3—C4—C10	116.51 (16)	C21B—C20—H20D	110.1
C3—C4—C5	112.06 (17)	O3—C20—H20D	110.1
C10—C4—C5	103.33 (15)	C21A—C20—H20D	62.2
C3—C4—H4	108.2	H20A—C20—H20D	139.5
C10—C4—H4	108.2	H20B—C20—H20D	50.5
C5—C4—H4	108.2	H20C—C20—H20D	108.4
N2—C5—C6	105.00 (18)	C20—C21A—H21A	109.5
N2—C5—C4	105.16 (17)	C20—C21A—H21B	109.5
C6—C5—C4	118.62 (19)	H21A—C21A—H21B	109.5
N2—C5—H5	109.2	C20—C21A—H21C	109.5
C6—C5—H5	109.2	H21A—C21A—H21C	109.5
C4—C5—H5	109.2	H21B—C21A—H21C	109.5
C5—C6—C7	102.5 (2)	C20—C21B—H21D	109.5
C5—C6—H6A	111.3	C20—C21B—H21E	109.5
C7—C6—H6A	111.3	H21D—C21B—H21E	109.5
C5—C6—H6B	111.3	C20—C21B—H21F	109.5
C7—C6—H6B	111.3	H21D—C21B—H21F	109.5
H6A—C6—H6B	109.2	H21E—C21B—H21F	109.5
C8—C7—C6	104.1 (2)	C23—C22—O2	115.0 (2)
C8—C7—H7A	110.9	C23—C22—C27	120.5 (2)
C6—C7—H7A	110.9	O2—C22—C27	124.6 (2)
C8—C7—H7B	110.9	C22—C23—C24	119.0 (3)
C6—C7—H7B	110.9	C22—C23—H23	120.5
H7A—C7—H7B	109.0	C24—C23—H23	120.5
N2—C8—C7	104.5 (2)	C23—C24—C25	120.5 (3)
N2—C8—H8A	110.9	C23—C24—H24	119.7
C7—C8—H8A	110.9	C25—C24—H24	119.7
N2—C8—H8B	110.9	C26—C25—C24	120.2 (3)
C7—C8—H8B	110.9	C26—C25—H25	119.9
H8A—C8—H8B	108.9	C24—C25—H25	119.9
N2—C9—C11	118.21 (17)	C25—C26—C27	119.8 (3)
N2—C9—C18	113.43 (17)	C25—C26—H26	120.1
C11—C9—C18	102.45 (17)	C27—C26—H26	120.1
N2—C9—C10	102.57 (16)	C26—C27—C22	120.1 (3)
C11—C9—C10	111.24 (16)	C26—C27—H27	120.0
C18—C9—C10	108.94 (16)	C22—C27—H27	120.0
C19—C10—C4	113.86 (16)	C33—C28—C29	119.4 (2)
C19—C10—C9	113.61 (17)	C33—C28—N1	121.92 (18)
C4—C10—C9	102.83 (15)	C29—C28—N1	118.6 (2)
C19—C10—H10	108.8	C30—C29—C28	119.9 (2)
C4—C10—H10	108.8	C30—C29—H29	120.1
C9—C10—H10	108.8	C28—C29—H29	120.1
O6—C11—C12	126.1 (2)	C29—C30—C31	120.8 (2)
O6—C11—C9	125.9 (2)	C29—C30—H30	119.6
C12—C11—C9	107.97 (18)	C31—C30—H30	119.6
C13—C12—C17	120.7 (2)	O7—C31—C32	124.8 (2)
C13—C12—C11	129.3 (2)	O7—C31—C30	116.1 (2)
C17—C12—C11	110.0 (2)	C32—C31—C30	119.2 (2)
C14—C13—C12	117.9 (3)	C31—C32—C33	120.1 (2)
C14—C13—H13	121.0	C31—C32—H32	120.0
C12—C13—H13	121.0	C33—C32—H32	120.0
C13—C14—C15	121.4 (3)	C28—C33—C32	120.7 (2)
C13—C14—H14	119.3	C28—C33—H33	119.7
C15—C14—H14	119.3	C32—C33—H33	119.7
C16—C15—C14	121.3 (3)	O7—C34—H34A	109.5
C16—C15—H15	119.4	O7—C34—H34B	109.5
C14—C15—H15	119.4	H34A—C34—H34B	109.5
C15—C16—C17	117.9 (3)	O7—C34—H34C	109.5
C15—C16—H16	121.0	H34A—C34—H34C	109.5
C17—C16—H16	121.0	H34B—C34—H34C	109.5
C16—C17—C12	120.7 (2)	C1—N1—C28	129.38 (17)
C16—C17—C18	128.8 (2)	C1—N1—C3	95.32 (16)
C12—C17—C18	110.47 (19)	C28—N1—C3	130.41 (17)
O5—C18—C17	127.1 (2)	C9—N2—C5	112.32 (15)
O5—C18—C9	125.1 (2)	C9—N2—C8	120.9 (2)
C17—C18—C9	107.81 (18)	C5—N2—C8	109.91 (18)
O4—C19—O3	124.3 (2)	C22—O2—C2	116.54 (16)
O4—C19—C10	124.9 (2)	C19—O3—C20	116.7 (2)
O3—C19—C10	110.83 (18)	C31—O7—C34	118.0 (2)
O1—C1—C2—O2	58.3 (4)	C11—C9—C18—C17	−10.5 (2)
N1—C1—C2—O2	−123.46 (19)	C10—C9—C18—C17	107.36 (19)
O1—C1—C2—C3	178.1 (3)	C4—C10—C19—O4	33.5 (3)
N1—C1—C2—C3	−3.69 (16)	C9—C10—C19—O4	−83.8 (3)
O2—C2—C3—N1	123.2 (2)	C4—C10—C19—O3	−147.20 (18)
C1—C2—C3—N1	3.39 (15)	C9—C10—C19—O3	95.5 (2)
O2—C2—C3—C4	4.2 (3)	O2—C22—C23—C24	−179.9 (3)
C1—C2—C3—C4	−115.6 (2)	C27—C22—C23—C24	−0.5 (4)
N1—C3—C4—C10	−54.3 (2)	C22—C23—C24—C25	0.1 (6)
C2—C3—C4—C10	47.9 (3)	C23—C24—C25—C26	0.0 (7)
N1—C3—C4—C5	−172.95 (17)	C24—C25—C26—C27	0.3 (7)
C2—C3—C4—C5	−70.8 (2)	C25—C26—C27—C22	−0.7 (6)
C3—C4—C5—N2	150.00 (17)	C23—C22—C27—C26	0.8 (4)
C10—C4—C5—N2	23.8 (2)	O2—C22—C27—C26	−179.9 (3)
C3—C4—C5—C6	−93.0 (3)	C33—C28—C29—C30	0.9 (4)
C10—C4—C5—C6	140.7 (2)	N1—C28—C29—C30	177.6 (3)
N2—C5—C6—C7	−29.2 (3)	C28—C29—C30—C31	0.3 (5)
C4—C5—C6—C7	−146.3 (2)	C29—C30—C31—O7	179.4 (3)
C5—C6—C7—C8	37.7 (3)	C29—C30—C31—C32	−1.1 (4)
C6—C7—C8—N2	−31.8 (3)	O7—C31—C32—C33	−179.8 (2)
C3—C4—C10—C19	77.5 (2)	C30—C31—C32—C33	0.8 (4)
C5—C4—C10—C19	−159.12 (17)	C29—C28—C33—C32	−1.2 (4)
C3—C4—C10—C9	−159.09 (17)	N1—C28—C33—C32	−177.8 (2)
C5—C4—C10—C9	−35.8 (2)	C31—C32—C33—C28	0.3 (4)
N2—C9—C10—C19	158.22 (17)	O1—C1—N1—C28	25.5 (4)
C11—C9—C10—C19	30.9 (2)	C2—C1—N1—C28	−152.9 (2)
C18—C9—C10—C19	−81.3 (2)	O1—C1—N1—C3	−177.8 (3)
N2—C9—C10—C4	34.68 (19)	C2—C1—N1—C3	3.88 (17)
C11—C9—C10—C4	−92.64 (19)	C33—C28—N1—C1	179.3 (2)
C18—C9—C10—C4	155.16 (17)	C29—C28—N1—C1	2.7 (4)
N2—C9—C11—O6	−42.0 (3)	C33—C28—N1—C3	30.4 (3)
C18—C9—C11—O6	−167.5 (2)	C29—C28—N1—C3	−146.2 (2)
C10—C9—C11—O6	76.2 (3)	C4—C3—N1—C1	118.5 (2)
N2—C9—C11—C12	136.57 (18)	C2—C3—N1—C1	−3.80 (17)
C18—C9—C11—C12	11.1 (2)	C4—C3—N1—C28	−85.1 (3)
C10—C9—C11—C12	−105.17 (18)	C2—C3—N1—C28	152.6 (2)
O6—C11—C12—C13	−8.3 (4)	C11—C9—N2—C5	102.0 (2)
C9—C11—C12—C13	173.2 (2)	C18—C9—N2—C5	−138.09 (18)
O6—C11—C12—C17	170.6 (2)	C10—C9—N2—C5	−20.8 (2)
C9—C11—C12—C17	−8.0 (2)	C11—C9—N2—C8	−30.4 (3)
C17—C12—C13—C14	−0.8 (4)	C18—C9—N2—C8	89.5 (2)
C11—C12—C13—C14	178.0 (2)	C10—C9—N2—C8	−153.2 (2)
C12—C13—C14—C15	0.0 (5)	C6—C5—N2—C9	−127.4 (2)
C13—C14—C15—C16	0.6 (5)	C4—C5—N2—C9	−1.5 (2)
C14—C15—C16—C17	−0.3 (4)	C6—C5—N2—C8	10.2 (3)
C15—C16—C17—C12	−0.5 (3)	C4—C5—N2—C8	136.1 (2)
C15—C16—C17—C18	−179.1 (2)	C7—C8—N2—C9	146.9 (2)
C13—C12—C17—C16	1.0 (3)	C7—C8—N2—C5	13.5 (3)
C11—C12—C17—C16	−177.95 (19)	C23—C22—O2—C2	176.5 (2)
C13—C12—C17—C18	179.9 (2)	C27—C22—O2—C2	−2.9 (3)
C11—C12—C17—C18	0.9 (2)	C1—C2—O2—C22	−75.8 (2)
C16—C17—C18—O5	4.5 (4)	C3—C2—O2—C22	−177.18 (18)
C12—C17—C18—O5	−174.2 (2)	O4—C19—O3—C20	−1.9 (4)
C16—C17—C18—C9	−174.8 (2)	C10—C19—O3—C20	178.8 (2)
C12—C17—C18—C9	6.4 (2)	C21B—C20—O3—C19	−86.4 (6)
N2—C9—C18—O5	41.5 (3)	C21A—C20—O3—C19	86.9 (2)
C11—C9—C18—O5	170.1 (2)	C32—C31—O7—C34	4.3 (4)
C10—C9—C18—O5	−72.0 (3)	C30—C31—O7—C34	−176.3 (3)
N2—C9—C18—C17	−139.10 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6i	0.98	2.45	3.151 (3)	129
C26—H26···O1ii	0.93	2.50	3.390 (4)	160
C8—H8A···O6	0.97	2.50	3.166 (4)	126
C10—H10···O2	0.98	2.24	2.987 (3)	132
C29—H29···O1	0.93	2.40	3.024 (3)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6i	0.98	2.45	3.151 (3)	129
C26—H26⋯O1ii	0.93	2.50	3.390 (4)	160
C8—H8A⋯O6	0.97	2.50	3.166 (4)	126
C10—H10⋯O2	0.98	2.24	2.987 (3)	132
C29—H29⋯O1	0.93	2.40	3.024 (3)	125

Symmetry codes: (i) ; (ii) .