1-(Benzyl­ideneacet­yl)-2-phenyl-1,2,3,5,10,10a-hexa­hydro-1H-pyrrolo[1,2-b]isoquinoline-3-spiro-3′(2′H)-1H-indol-3′-one

Gayathri, D.; Sethukkarasi, R.M.; Velmurugan, D.; Ravikumar, K.; Periyasami, G.

doi:10.1107/S160053680703348X

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1-(Benzylideneacetyl)-2-phenyl-1,2,3,5,10,10a-hexahydro-1H-pyrrolo[1,2-b]isoquinoline-3-spiro-3′(2′H)-1H-indol-3′-one

D. Gayathri, R. M. Sethukkarasi, D. Velmurugan, K. Ravikumar and G. Periyasami

The pyrrolidine ring in the title compound, C₃₄H₂₈N₂O₂, adopts a twist conformation in one of the two independent molecules and an envelope conformation in the other. The oxindole group in both molecules is planar. The molecular structure is stabilized by weak intramolecular C—H

O interactions and the crystal packing is stabilized by intermolecular N—H

O interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703348X/pr2006sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680703348X/pr2006Isup2.hkl Contains datablock I

CCDC reference: 657758

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.050
wR factor = 0.122
Data-to-parameter ratio = 9.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C61
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C57

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.06
           From the CIF: _reflns_number_total               6482
           Count of symmetry unique reflns         6624
           Completeness (_total/calc)             97.86%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT792_ALERT_1_G Check the Absolute Configuration of C1     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C2     = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C3     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C4     = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C35    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C36    = ...          R
PLAT792_ALERT_1_G Check the Absolute Configuration of C37    = ...          S
PLAT792_ALERT_1_G Check the Absolute Configuration of C38    = ...          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
  12 ALERT level G = General alerts; check

  10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Pyrrolidine occurs widely in nature and is a structural part of porphyrin heme, chlorophyll and vitamin B12. Pyrrolidine compounds have antifungal and antimicrobial activity (Amal Raj et al., 2003). The spiro ring system is a frequently encountered structural motif in many pharmacologically relevant alkaloids. Synthetic spiro-pyrrolidine derivatives have activity against the aldose reductase enzyme which controls influenza (Stylianakis et al., 2003). As spiropyrrolidine compounds are of great pharmaceutical importance, we have undertaken the three dimensional crystal structure determination of the title compound, C₃₄ H₂₈ N₂ O₂, by X-ray diffraction (Fig.1).

The bond lengths and angles are comparable with the literature values (Allen et al., 1987). The sum of the bond angles around N1 (339.5 (6)°) and N3 (336.0 (6)°) indicates the sp³ hybridization. The pyrrolidine ring in molecule A adopts a twisted conformation with a pseudo twofold axis passing through atom C1 and C3—C4 bond. In molecule B, it adopts an envelope conformation with atom C38 deviating by -0.608 (2)Å from the plane of rest of the atoms in the ring. The six membered rings N1/C4—C6/C11/C12 and N3/C38—C40/C45/C46 in molecules A and B, respectively, are non-planar. The oxindole ring in molecules A and B is planar with the dihedral angle between five and six membered rings being 2.3 (1) and 1.8 (1)°, respectively. Oxygen atoms O1 and O3 lie below the plane of the five membered rings in the oxindole moiety in molecule A and B by 0.021 (2) and 0.049 (2) Å, respectively.

The puckering parameters (Cremer & Pople, 1975) and the smallest displacement asymmetry parameters (Nardelli, 1983) for pyrrolidine ring N1/C1—C4 in the molecule A are q₂ = 0.392 (3) Å, φ = 310.6 (4)° and Δ ₂(C₁) = 7.5 (2), for pyrrolidine ring N3/C35—C38 in the molecule B are q₂ = 0.400 (3) Å, φ = 152.0 (4)° and Δ _s(C₃₈) = 9.7 (2), for six memebered rings (N1/C4—C6/C11/C12 and N3/C38—C40/C45/C46) in molecule A and B are q2 = 0.394 (3) Å; 0.369 (3) Å, q3 = 0.328 (3) Å; -0.314 (3) Å, Q_T = 0.513 (3) Å; 0.485 (3)Å and θ = 50.2 (3)°; s130.4(3)°, respectively.

The molecule is stabilized by weak C—H···O intramolecular interactions. The crystal packing is stabilized by two N—H···O intermolecular interactions. Atoms N2 and N4 act as donors to O4 (1/2 + x,1 - y,z) and O2 (-1/2 + x,-y,z), generating a chain running along b axis.

Related literature top

For related literature, see: Allen et al. (1987); Amal Raj et al. (2003); Cremer & Pople (1975); Nardelli (1983); Stylianakis et al. (2003).

Experimental top

A mixture of isoquinolic aicd (0.186 g, 1 mmol), isatin (0.147 g, 1 mmol), bis-benzylidine acetone (0.224 g, 1 mmol) and triethyl amine (0.252 g, 2.5 mmol) was refluxed in acetonitrile for 12 h. The reaction was monitored by TLC and after completion, the solvent was removed at reduced pressure. The crude product was subjected to column chromatrography (Silica gel, 100–200 mesh) using Hexane/Ethyl acetate (9:1) as eluent. The compound was recrystallized from Hexane/Ethyl acetate (1:1) by slow evaporation.

Structure description top

For related literature, see: Allen et al. (1987); Amal Raj et al. (2003); Cremer & Pople (1975); Nardelli (1983); Stylianakis et al. (2003).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top

	Fig. 1. The molecular structure of title compound, showing 30% probability displacement ellipsoids.
	Fig. 2. The molecular packing of (I), viewed down the c axis. For clarity, hydrogen atoms which are not involved in hydrogen bonding were omitted.

1-(Benzylideneacetyl)-2-phenyl-1,2,3,5,10,10a-hexahydro- 1H-pyrrolo[1,2-b]isoquinoline-3-spiro-3'(2'H)-1H- indol-3'-one top

Crystal data top

C₃₄H₂₈N₂O₂	F(000) = 2096
M_r = 496.58	D_x = 1.249 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3158 reflections
a = 19.301 (4) Å	θ = 1.4–25.0°
b = 14.725 (3) Å	µ = 0.08 mm⁻¹
c = 18.583 (4) Å	T = 293 K
V = 5281 (2) Å³	Block, colourless
Z = 8	0.28 × 0.24 × 0.23 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.030
Graphite monochromator	θ_max = 28.1°, θ_min = 1.4°
ω scans	h = −25→25
44375 measured reflections	k = −19→19
6482 independent reflections	l = −23→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0723P)² + 0.0694P] where P = (F_o² + 2F_c²)/3
6482 reflections	(Δ/σ)_max < 0.001
685 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₃₄H₂₈N₂O₂	V = 5281 (2) Å³
M_r = 496.58	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 19.301 (4) Å	µ = 0.08 mm⁻¹
b = 14.725 (3) Å	T = 293 K
c = 18.583 (4) Å	0.28 × 0.24 × 0.23 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5365 reflections with I > 2σ(I)
44375 measured reflections	R_int = 0.030
6482 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.122	H-atom parameters constrained
S = 1.12	Δρ_max = 0.26 e Å⁻³
6482 reflections	Δρ_min = −0.13 e Å⁻³
685 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.46079 (10)	0.50133 (13)	0.42242 (11)	0.0422 (4)
N2	0.62533 (12)	0.58129 (15)	0.45090 (14)	0.0587 (6)
H2	0.6587	0.6178	0.4406	0.070*
O1	0.59608 (10)	0.53639 (13)	0.33659 (12)	0.0601 (5)
O2	0.54648 (10)	0.24727 (13)	0.49803 (11)	0.0581 (5)
C1	0.53286 (12)	0.47841 (16)	0.44209 (13)	0.0403 (5)
C2	0.53957 (12)	0.37561 (14)	0.42011 (13)	0.0403 (5)
H2A	0.5671	0.3732	0.3758	0.048*
C3	0.46564 (12)	0.34610 (15)	0.40080 (13)	0.0402 (5)
H3	0.4416	0.3289	0.4452	0.048*
C4	0.43374 (12)	0.43268 (15)	0.37264 (13)	0.0432 (5)
H4	0.4503	0.4449	0.3237	0.052*
C5	0.35535 (13)	0.43692 (18)	0.37494 (16)	0.0526 (6)
H5A	0.3364	0.3977	0.3379	0.063*
H5B	0.3392	0.4150	0.4212	0.063*
C6	0.32979 (13)	0.53207 (18)	0.36345 (14)	0.0512 (6)
C7	0.26194 (15)	0.5487 (2)	0.34094 (17)	0.0632 (7)
H7	0.2320	0.5000	0.3337	0.076*
C8	0.23858 (17)	0.6352 (3)	0.32928 (19)	0.0743 (9)
H8	0.1934	0.6447	0.3136	0.089*
C9	0.28120 (18)	0.7074 (3)	0.3405 (2)	0.0788 (10)
H9	0.2650	0.7662	0.3335	0.095*
C10	0.34873 (17)	0.6929 (2)	0.36238 (18)	0.0659 (8)
H10	0.3781	0.7423	0.3688	0.079*
C11	0.37348 (14)	0.60568 (18)	0.37491 (14)	0.0513 (6)
C12	0.44767 (14)	0.59353 (17)	0.39869 (18)	0.0550 (6)
H12A	0.4784	0.6081	0.3590	0.066*
H12B	0.4576	0.6352	0.4378	0.066*
C13	0.58798 (12)	0.53482 (15)	0.40082 (16)	0.0467 (5)
C14	0.60314 (14)	0.56264 (18)	0.52101 (16)	0.0542 (6)
C15	0.62925 (19)	0.5944 (3)	0.5859 (2)	0.0797 (10)
H15	0.6656	0.6358	0.5873	0.096*
C16	0.5996 (2)	0.5626 (3)	0.6476 (2)	0.0880 (11)
H16	0.6165	0.5830	0.6916	0.106*
C17	0.54584 (18)	0.5018 (3)	0.64710 (18)	0.0746 (9)
H17	0.5273	0.4810	0.6902	0.090*
C18	0.51918 (14)	0.47146 (19)	0.58210 (16)	0.0543 (6)
H18	0.4822	0.4310	0.5811	0.065*
C19	0.54836 (12)	0.50215 (16)	0.51922 (14)	0.0445 (5)
C20	0.57527 (12)	0.31515 (16)	0.47504 (13)	0.0434 (5)
C21	0.64594 (12)	0.33979 (16)	0.49544 (14)	0.0468 (6)
H21	0.6688	0.3841	0.4688	0.056*
C22	0.67879 (13)	0.30178 (18)	0.55021 (15)	0.0494 (6)
H22	0.6552	0.2560	0.5745	0.059*
C23	0.74793 (14)	0.32391 (17)	0.57657 (14)	0.0497 (6)
C24	0.78893 (15)	0.3894 (2)	0.54376 (17)	0.0622 (7)
H24	0.7723	0.4202	0.5037	0.075*
C25	0.85405 (16)	0.4092 (2)	0.56991 (19)	0.0698 (8)
H25	0.8810	0.4531	0.5473	0.084*
C26	0.87937 (17)	0.3645 (2)	0.62915 (19)	0.0689 (8)
H26	0.9231	0.3784	0.6470	0.083*
C27	0.83963 (17)	0.2994 (2)	0.66163 (18)	0.0705 (8)
H27	0.8568	0.2686	0.7015	0.085*
C28	0.77457 (15)	0.2788 (2)	0.63601 (17)	0.0626 (7)
H28	0.7483	0.2342	0.6587	0.075*
C29	0.46236 (12)	0.26695 (15)	0.34907 (13)	0.0419 (5)
C30	0.49026 (15)	0.27250 (18)	0.28099 (14)	0.0513 (6)
H30	0.5118	0.3258	0.2663	0.062*
C31	0.48653 (17)	0.1997 (2)	0.23432 (16)	0.0645 (8)
H31	0.5053	0.2045	0.1884	0.077*
C32	0.45541 (18)	0.1202 (2)	0.2553 (2)	0.0717 (9)
H32	0.4529	0.0712	0.2238	0.086*
C33	0.42797 (19)	0.1138 (2)	0.3231 (2)	0.0755 (9)
H33	0.4072	0.0600	0.3380	0.091*
C34	0.43110 (16)	0.18685 (19)	0.36949 (17)	0.0605 (7)
H34	0.4118	0.1820	0.4152	0.073*
N3	0.30081 (10)	0.01027 (14)	0.48973 (11)	0.0431 (4)
N4	0.13746 (12)	−0.08201 (15)	0.46957 (14)	0.0538 (5)
H4A	0.1044	−0.1181	0.4817	0.065*
O3	0.17250 (10)	−0.03839 (14)	0.58196 (11)	0.0622 (5)
O4	0.22277 (11)	0.26153 (13)	0.42423 (12)	0.0629 (5)
C35	0.22770 (12)	0.02546 (15)	0.47260 (13)	0.0404 (5)
C36	0.21591 (12)	0.12748 (15)	0.49559 (13)	0.0415 (5)
H36	0.1801	0.1271	0.5330	0.050*
C37	0.28381 (12)	0.15756 (16)	0.53213 (13)	0.0419 (5)
H37	0.3125	0.1880	0.4959	0.050*
C38	0.31875 (12)	0.06702 (15)	0.55144 (13)	0.0423 (5)
H38	0.2978	0.0420	0.5952	0.051*
C39	0.39667 (14)	0.07150 (18)	0.56000 (16)	0.0546 (6)
H39A	0.4155	0.1128	0.5243	0.066*
H39B	0.4076	0.0957	0.6072	0.066*
C40	0.43057 (12)	−0.02032 (19)	0.55155 (14)	0.0514 (6)
C41	0.49887 (14)	−0.0325 (2)	0.57275 (16)	0.0615 (7)
H41	0.5236	0.0162	0.5917	0.074*
C42	0.53040 (15)	−0.1157 (3)	0.56606 (17)	0.0717 (9)
H42	0.5763	−0.1229	0.5803	0.086*
C43	0.49443 (17)	−0.1884 (3)	0.53838 (19)	0.0723 (9)
H43	0.5158	−0.2448	0.5344	0.087*
C44	0.42672 (16)	−0.1777 (2)	0.51665 (17)	0.0646 (8)
H44	0.4024	−0.2268	0.4979	0.078*
C45	0.39465 (14)	−0.09327 (19)	0.52270 (14)	0.0517 (6)
C46	0.31998 (14)	−0.08480 (18)	0.49940 (17)	0.0564 (7)
H46A	0.3133	−0.1173	0.4545	0.068*
H46B	0.2902	−0.1121	0.5354	0.068*
C47	0.17671 (12)	−0.03513 (16)	0.51703 (15)	0.0459 (5)
C48	0.15689 (13)	−0.06487 (17)	0.39832 (16)	0.0503 (6)
C49	0.12964 (18)	−0.1014 (2)	0.3361 (2)	0.0708 (9)
H49	0.0932	−0.1426	0.3375	0.085*
C50	0.1583 (2)	−0.0746 (3)	0.2723 (2)	0.0866 (11)
H50	0.1403	−0.0974	0.2295	0.104*
C51	0.2136 (2)	−0.0145 (3)	0.26936 (19)	0.0803 (10)
H51	0.2331	0.0010	0.2253	0.096*
C52	0.23952 (17)	0.02232 (19)	0.33228 (16)	0.0598 (7)
H52	0.2761	0.0635	0.3308	0.072*
C53	0.21077 (13)	−0.00253 (16)	0.39683 (14)	0.0452 (5)
C54	0.19103 (13)	0.19223 (16)	0.43715 (14)	0.0446 (5)
C55	0.12545 (13)	0.17004 (17)	0.40118 (15)	0.0487 (6)
H55	0.0979	0.1239	0.4199	0.058*
C56	0.10429 (14)	0.21369 (19)	0.34293 (16)	0.0547 (6)
H56	0.1323	0.2612	0.3275	0.066*
C57	0.04232 (16)	0.1963 (2)	0.29999 (16)	0.0574 (7)
C58	−0.00864 (18)	0.1359 (2)	0.3203 (2)	0.0738 (9)
H58	−0.0046	0.1045	0.3635	0.089*
C59	−0.0659 (2)	0.1219 (2)	0.2767 (3)	0.0885 (12)
H59	−0.1006	0.0821	0.2913	0.106*
C60	−0.0717 (2)	0.1664 (3)	0.2121 (2)	0.0898 (13)
H60	−0.1091	0.1548	0.1819	0.108*
C61	−0.0228 (3)	0.2269 (4)	0.1927 (2)	0.1200 (18)
H61	−0.0274	0.2585	0.1497	0.144*
C62	0.0339 (2)	0.2423 (3)	0.2362 (2)	0.0962 (13)
H62	0.0670	0.2847	0.2221	0.115*
C63	0.27609 (13)	0.22087 (17)	0.59528 (15)	0.0483 (6)
C64	0.23529 (16)	0.1990 (2)	0.65397 (16)	0.0600 (7)
H64	0.2100	0.1452	0.6535	0.072*
C65	0.2313 (2)	0.2548 (3)	0.71295 (19)	0.0781 (10)
H65	0.2038	0.2385	0.7519	0.094*
C66	0.2676 (2)	0.3339 (3)	0.7146 (2)	0.0886 (12)
H66	0.2651	0.3714	0.7548	0.106*
C67	0.3075 (2)	0.3580 (2)	0.6576 (3)	0.0885 (12)
H67	0.3320	0.4124	0.6587	0.106*
C68	0.31184 (16)	0.3019 (2)	0.5973 (2)	0.0668 (8)
H68	0.3390	0.3192	0.5584	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0385 (10)	0.0402 (10)	0.0480 (11)	0.0028 (8)	−0.0090 (8)	−0.0060 (8)
N2	0.0500 (13)	0.0505 (13)	0.0755 (17)	−0.0118 (10)	−0.0073 (11)	−0.0034 (12)
O1	0.0590 (11)	0.0635 (12)	0.0577 (12)	−0.0005 (9)	0.0036 (9)	0.0076 (9)
O2	0.0575 (11)	0.0499 (10)	0.0669 (12)	−0.0013 (8)	−0.0082 (9)	0.0105 (9)
C1	0.0405 (12)	0.0371 (11)	0.0432 (12)	0.0030 (9)	−0.0041 (9)	−0.0039 (9)
C2	0.0429 (12)	0.0361 (11)	0.0420 (12)	0.0009 (9)	0.0000 (9)	−0.0036 (9)
C3	0.0409 (11)	0.0416 (11)	0.0380 (11)	−0.0013 (9)	0.0004 (9)	−0.0026 (10)
C4	0.0460 (13)	0.0426 (12)	0.0409 (12)	0.0029 (10)	−0.0060 (10)	−0.0043 (10)
C5	0.0439 (13)	0.0541 (14)	0.0599 (16)	−0.0005 (11)	−0.0101 (11)	−0.0085 (12)
C6	0.0465 (13)	0.0630 (15)	0.0440 (13)	0.0062 (12)	−0.0032 (11)	−0.0068 (12)
C7	0.0487 (15)	0.0853 (19)	0.0555 (16)	0.0106 (14)	−0.0086 (13)	−0.0087 (15)
C8	0.0513 (17)	0.103 (3)	0.069 (2)	0.0255 (18)	−0.0135 (15)	0.0011 (19)
C9	0.074 (2)	0.082 (2)	0.080 (2)	0.0339 (19)	−0.0092 (18)	0.0144 (19)
C10	0.0651 (18)	0.0601 (16)	0.072 (2)	0.0130 (14)	−0.0058 (15)	0.0103 (15)
C11	0.0525 (14)	0.0536 (14)	0.0479 (14)	0.0106 (12)	−0.0055 (11)	−0.0009 (11)
C12	0.0515 (14)	0.0408 (12)	0.0729 (17)	0.0055 (11)	−0.0098 (13)	−0.0023 (13)
C13	0.0442 (13)	0.0383 (12)	0.0575 (16)	0.0033 (10)	−0.0041 (11)	0.0019 (11)
C14	0.0520 (14)	0.0497 (14)	0.0609 (16)	0.0032 (11)	−0.0098 (12)	−0.0133 (13)
C15	0.070 (2)	0.081 (2)	0.088 (3)	−0.0124 (17)	−0.0209 (19)	−0.026 (2)
C16	0.087 (2)	0.119 (3)	0.058 (2)	−0.006 (2)	−0.0176 (18)	−0.028 (2)
C17	0.074 (2)	0.100 (3)	0.0504 (18)	0.0078 (19)	−0.0034 (15)	−0.0125 (17)
C18	0.0539 (15)	0.0588 (15)	0.0504 (15)	0.0049 (12)	−0.0047 (12)	−0.0076 (12)
C19	0.0433 (12)	0.0403 (12)	0.0498 (14)	0.0072 (10)	−0.0104 (10)	−0.0093 (11)
C20	0.0469 (13)	0.0387 (12)	0.0447 (13)	0.0053 (10)	−0.0010 (10)	−0.0039 (10)
C21	0.0454 (12)	0.0423 (12)	0.0527 (14)	0.0041 (10)	−0.0005 (11)	0.0055 (11)
C22	0.0484 (13)	0.0522 (14)	0.0476 (13)	−0.0023 (11)	−0.0003 (11)	0.0047 (11)
C23	0.0470 (13)	0.0557 (14)	0.0462 (14)	0.0022 (12)	−0.0014 (11)	0.0016 (11)
C24	0.0584 (16)	0.0696 (17)	0.0585 (17)	−0.0050 (13)	−0.0082 (13)	0.0161 (14)
C25	0.0584 (17)	0.0731 (19)	0.078 (2)	−0.0158 (15)	−0.0037 (15)	0.0087 (16)
C26	0.0549 (16)	0.083 (2)	0.0691 (19)	−0.0074 (15)	−0.0147 (15)	−0.0039 (17)
C27	0.0664 (19)	0.090 (2)	0.0546 (17)	0.0014 (17)	−0.0169 (14)	0.0131 (16)
C28	0.0600 (17)	0.0762 (19)	0.0517 (16)	−0.0079 (14)	−0.0040 (13)	0.0137 (14)
C29	0.0421 (12)	0.0396 (12)	0.0440 (13)	−0.0008 (9)	−0.0014 (10)	−0.0034 (10)
C30	0.0642 (16)	0.0461 (13)	0.0437 (14)	−0.0075 (12)	0.0018 (12)	−0.0009 (11)
C31	0.080 (2)	0.0680 (18)	0.0454 (15)	−0.0018 (16)	0.0021 (14)	−0.0125 (13)
C32	0.084 (2)	0.0561 (17)	0.075 (2)	−0.0078 (15)	−0.0017 (17)	−0.0282 (16)
C33	0.085 (2)	0.0482 (15)	0.093 (3)	−0.0221 (15)	0.0184 (19)	−0.0138 (16)
C34	0.0669 (18)	0.0528 (15)	0.0617 (17)	−0.0094 (13)	0.0158 (14)	−0.0052 (13)
N3	0.0380 (9)	0.0465 (11)	0.0449 (11)	0.0043 (8)	−0.0035 (8)	0.0017 (8)
N4	0.0482 (12)	0.0454 (11)	0.0679 (14)	−0.0106 (9)	0.0023 (10)	0.0045 (10)
O3	0.0646 (12)	0.0704 (13)	0.0515 (12)	−0.0062 (10)	0.0080 (9)	0.0138 (10)
O4	0.0633 (12)	0.0512 (11)	0.0742 (14)	−0.0054 (9)	−0.0162 (10)	0.0170 (10)
C35	0.0390 (12)	0.0408 (12)	0.0415 (12)	−0.0024 (9)	−0.0006 (10)	0.0038 (10)
C36	0.0409 (12)	0.0437 (12)	0.0398 (12)	−0.0020 (9)	0.0014 (9)	0.0026 (9)
C37	0.0416 (12)	0.0439 (12)	0.0402 (12)	−0.0018 (9)	−0.0007 (9)	0.0045 (10)
C38	0.0430 (12)	0.0442 (12)	0.0399 (12)	−0.0008 (9)	−0.0021 (10)	0.0042 (10)
C39	0.0479 (14)	0.0581 (15)	0.0578 (16)	−0.0028 (11)	−0.0100 (12)	0.0070 (13)
C40	0.0419 (13)	0.0687 (16)	0.0436 (13)	0.0046 (11)	0.0018 (10)	0.0126 (12)
C41	0.0417 (13)	0.087 (2)	0.0553 (16)	0.0042 (14)	0.0023 (12)	0.0156 (15)
C42	0.0424 (14)	0.113 (3)	0.0598 (18)	0.0214 (17)	0.0077 (13)	0.0180 (18)
C43	0.0666 (19)	0.090 (2)	0.0602 (18)	0.0373 (18)	0.0085 (15)	0.0073 (16)
C44	0.0651 (17)	0.0672 (18)	0.0616 (17)	0.0219 (14)	0.0024 (14)	−0.0005 (14)
C45	0.0482 (13)	0.0626 (15)	0.0444 (13)	0.0119 (12)	0.0033 (11)	0.0058 (12)
C46	0.0514 (15)	0.0485 (14)	0.0692 (18)	0.0086 (11)	−0.0094 (13)	−0.0040 (13)
C47	0.0406 (12)	0.0412 (12)	0.0558 (15)	0.0031 (10)	0.0012 (11)	0.0086 (11)
C48	0.0468 (13)	0.0425 (12)	0.0617 (15)	−0.0005 (11)	−0.0073 (12)	−0.0001 (12)
C49	0.077 (2)	0.0605 (17)	0.075 (2)	−0.0126 (15)	−0.0192 (18)	−0.0099 (16)
C50	0.110 (3)	0.082 (2)	0.067 (2)	−0.009 (2)	−0.028 (2)	−0.0163 (19)
C51	0.105 (3)	0.085 (2)	0.0504 (18)	−0.005 (2)	−0.0063 (17)	0.0003 (16)
C52	0.0709 (18)	0.0601 (16)	0.0483 (15)	−0.0069 (14)	−0.0005 (13)	0.0013 (13)
C53	0.0452 (12)	0.0418 (12)	0.0485 (13)	0.0039 (10)	−0.0063 (10)	−0.0015 (11)
C54	0.0481 (13)	0.0409 (13)	0.0449 (13)	0.0060 (10)	−0.0016 (10)	0.0010 (10)
C55	0.0444 (13)	0.0466 (13)	0.0551 (14)	0.0035 (10)	−0.0042 (11)	0.0045 (11)
C56	0.0590 (15)	0.0524 (14)	0.0525 (15)	0.0034 (12)	−0.0055 (12)	0.0037 (12)
C57	0.0609 (17)	0.0590 (16)	0.0523 (15)	0.0122 (13)	−0.0124 (12)	−0.0038 (12)
C58	0.078 (2)	0.0532 (16)	0.091 (2)	0.0015 (15)	−0.0312 (18)	0.0114 (16)
C59	0.082 (2)	0.0533 (17)	0.130 (4)	0.0014 (16)	−0.046 (2)	−0.002 (2)
C60	0.097 (3)	0.085 (2)	0.087 (3)	0.018 (2)	−0.050 (2)	−0.016 (2)
C61	0.111 (4)	0.179 (5)	0.071 (3)	−0.002 (4)	−0.042 (3)	0.028 (3)
C62	0.089 (3)	0.133 (4)	0.067 (2)	−0.011 (2)	−0.0248 (19)	0.028 (2)
C63	0.0493 (14)	0.0438 (13)	0.0519 (15)	0.0064 (10)	−0.0107 (11)	0.0011 (11)
C64	0.0723 (19)	0.0588 (16)	0.0488 (15)	0.0069 (14)	−0.0019 (14)	−0.0012 (13)
C65	0.091 (2)	0.089 (2)	0.0540 (18)	0.027 (2)	−0.0041 (16)	−0.0077 (17)
C66	0.099 (3)	0.087 (3)	0.080 (3)	0.021 (2)	−0.017 (2)	−0.036 (2)
C67	0.084 (2)	0.059 (2)	0.123 (4)	−0.0040 (17)	−0.020 (2)	−0.029 (2)
C68	0.0649 (18)	0.0544 (16)	0.081 (2)	−0.0040 (13)	−0.0079 (16)	−0.0097 (15)

Geometric parameters (Å, º) top

N1—C12	1.450 (3)	N3—C46	1.459 (3)
N1—C4	1.466 (3)	N3—C38	1.461 (3)
N1—C1	1.477 (3)	N3—C35	1.464 (3)
N2—C13	1.362 (4)	N4—C47	1.352 (4)
N2—C14	1.399 (4)	N4—C48	1.399 (4)
N2—H2	0.8600	N4—H4A	0.8600
O1—C13	1.204 (3)	O3—C47	1.210 (3)
O2—C20	1.221 (3)	O4—C54	1.214 (3)
C1—C19	1.505 (3)	C35—C53	1.503 (4)
C1—C13	1.552 (4)	C35—C47	1.564 (3)
C1—C2	1.573 (3)	C35—C36	1.578 (3)
C2—C20	1.520 (3)	C36—C54	1.523 (3)
C2—C3	1.534 (3)	C36—C37	1.541 (3)
C2—H2A	0.9800	C36—H36	0.9800
C3—C4	1.510 (3)	C37—C63	1.506 (3)
C3—C29	1.512 (3)	C37—C38	1.537 (3)
C3—H3	0.9800	C37—H37	0.9800
C4—C5	1.515 (4)	C38—C39	1.514 (3)
C4—H4	0.9800	C38—H38	0.9800
C5—C6	1.501 (4)	C39—C40	1.510 (4)
C5—H5A	0.9700	C39—H39A	0.9700
C5—H5B	0.9700	C39—H39B	0.9700
C6—C11	1.390 (4)	C40—C45	1.386 (4)
C6—C7	1.397 (4)	C40—C41	1.387 (4)
C7—C8	1.368 (4)	C41—C42	1.374 (5)
C7—H7	0.9300	C41—H41	0.9300
C8—C9	1.361 (5)	C42—C43	1.376 (5)
C8—H8	0.9300	C42—H42	0.9300
C9—C10	1.382 (4)	C43—C44	1.377 (5)
C9—H9	0.9300	C43—H43	0.9300
C10—C11	1.390 (4)	C44—C45	1.393 (4)
C10—H10	0.9300	C44—H44	0.9300
C11—C12	1.509 (4)	C45—C46	1.510 (4)
C12—H12A	0.9700	C46—H46A	0.9700
C12—H12B	0.9700	C46—H46B	0.9700
C14—C19	1.383 (4)	C48—C49	1.380 (4)
C14—C15	1.388 (4)	C48—C53	1.388 (4)
C15—C16	1.364 (6)	C49—C50	1.367 (6)
C15—H15	0.9300	C49—H49	0.9300
C16—C17	1.371 (6)	C50—C51	1.387 (6)
C16—H16	0.9300	C50—H50	0.9300
C17—C18	1.387 (4)	C51—C52	1.383 (5)
C17—H17	0.9300	C51—H51	0.9300
C18—C19	1.374 (4)	C52—C53	1.371 (4)
C18—H18	0.9300	C52—H52	0.9300
C20—C21	1.462 (3)	C54—C55	1.468 (4)
C21—C22	1.323 (4)	C55—C56	1.323 (4)
C21—H21	0.9300	C55—H55	0.9300
C22—C23	1.459 (4)	C56—C57	1.460 (4)
C22—H22	0.9300	C56—H56	0.9300
C23—C28	1.388 (4)	C57—C62	1.375 (5)
C23—C24	1.388 (4)	C57—C58	1.378 (5)
C24—C25	1.379 (4)	C58—C59	1.386 (5)
C24—H24	0.9300	C58—H58	0.9300
C25—C26	1.372 (5)	C59—C60	1.373 (6)
C25—H25	0.9300	C59—H59	0.9300
C26—C27	1.369 (5)	C60—C61	1.346 (7)
C26—H26	0.9300	C60—H60	0.9300
C27—C28	1.377 (4)	C61—C62	1.379 (6)
C27—H27	0.9300	C61—H61	0.9300
C28—H28	0.9300	C62—H62	0.9300
C29—C30	1.377 (4)	C63—C68	1.379 (4)
C29—C34	1.378 (4)	C63—C64	1.383 (4)
C30—C31	1.381 (4)	C64—C65	1.372 (5)
C30—H30	0.9300	C64—H64	0.9300
C31—C32	1.371 (5)	C65—C66	1.359 (6)
C31—H31	0.9300	C65—H65	0.9300
C32—C33	1.371 (5)	C66—C67	1.357 (6)
C32—H32	0.9300	C66—H66	0.9300
C33—C34	1.379 (4)	C67—C68	1.395 (5)
C33—H33	0.9300	C67—H67	0.9300
C34—H34	0.9300	C68—H68	0.9300

C12—N1—C4	113.0 (2)	C46—N3—C38	113.1 (2)
C12—N1—C1	117.0 (2)	C46—N3—C35	114.7 (2)
C4—N1—C1	109.5 (2)	C38—N3—C35	108.2 (2)
C13—N2—C14	112.1 (2)	C47—N4—C48	112.0 (2)
C13—N2—H2	124.0	C47—N4—H4A	124.0
C14—N2—H2	124.0	C48—N4—H4A	124.0
N1—C1—C19	111.70 (19)	N3—C35—C53	111.8 (2)
N1—C1—C13	113.62 (19)	N3—C35—C47	113.88 (19)
C19—C1—C13	102.1 (2)	C53—C35—C47	101.61 (19)
N1—C1—C2	103.47 (17)	N3—C35—C36	103.04 (18)
C19—C1—C2	117.0 (2)	C53—C35—C36	118.90 (19)
C13—C1—C2	109.28 (19)	C47—C35—C36	108.01 (18)
C20—C2—C3	114.39 (19)	C54—C36—C37	113.74 (19)
C20—C2—C1	115.25 (19)	C54—C36—C35	116.6 (2)
C3—C2—C1	104.88 (18)	C37—C36—C35	105.67 (18)
C20—C2—H2A	107.3	C54—C36—H36	106.7
C3—C2—H2A	107.3	C37—C36—H36	106.7
C1—C2—H2A	107.3	C35—C36—H36	106.7
C4—C3—C29	114.4 (2)	C63—C37—C38	113.5 (2)
C4—C3—C2	102.78 (18)	C63—C37—C36	115.9 (2)
C29—C3—C2	113.96 (19)	C38—C37—C36	103.11 (18)
C4—C3—H3	108.5	C63—C37—H37	108.0
C29—C3—H3	108.5	C38—C37—H37	108.0
C2—C3—H3	108.5	C36—C37—H37	108.0
N1—C4—C3	102.61 (18)	N3—C38—C39	110.1 (2)
N1—C4—C5	108.03 (19)	N3—C38—C37	102.06 (18)
C3—C4—C5	115.6 (2)	C39—C38—C37	115.0 (2)
N1—C4—H4	110.1	N3—C38—H38	109.8
C3—C4—H4	110.1	C39—C38—H38	109.8
C5—C4—H4	110.1	C37—C38—H38	109.8
C6—C5—C4	111.3 (2)	C40—C39—C38	112.4 (2)
C6—C5—H5A	109.4	C40—C39—H39A	109.1
C4—C5—H5A	109.4	C38—C39—H39A	109.1
C6—C5—H5B	109.4	C40—C39—H39B	109.1
C4—C5—H5B	109.4	C38—C39—H39B	109.1
H5A—C5—H5B	108.0	H39A—C39—H39B	107.9
C11—C6—C7	118.6 (3)	C45—C40—C41	119.0 (3)
C11—C6—C5	120.5 (2)	C45—C40—C39	121.1 (2)
C7—C6—C5	121.0 (3)	C41—C40—C39	119.8 (3)
C8—C7—C6	121.3 (3)	C42—C41—C40	120.7 (3)
C8—C7—H7	119.3	C42—C41—H41	119.7
C6—C7—H7	119.3	C40—C41—H41	119.7
C9—C8—C7	120.3 (3)	C41—C42—C43	120.3 (3)
C9—C8—H8	119.9	C41—C42—H42	119.9
C7—C8—H8	119.9	C43—C42—H42	119.9
C8—C9—C10	119.6 (3)	C42—C43—C44	119.9 (3)
C8—C9—H9	120.2	C42—C43—H43	120.0
C10—C9—H9	120.2	C44—C43—H43	120.0
C9—C10—C11	121.1 (3)	C43—C44—C45	120.0 (3)
C9—C10—H10	119.4	C43—C44—H44	120.0
C11—C10—H10	119.4	C45—C44—H44	120.0
C10—C11—C6	119.1 (3)	C40—C45—C44	120.0 (3)
C10—C11—C12	119.0 (3)	C40—C45—C46	121.6 (2)
C6—C11—C12	121.9 (2)	C44—C45—C46	118.3 (3)
N1—C12—C11	111.5 (2)	N3—C46—C45	110.9 (2)
N1—C12—H12A	109.3	N3—C46—H46A	109.5
C11—C12—H12A	109.3	C45—C46—H46A	109.5
N1—C12—H12B	109.3	N3—C46—H46B	109.5
C11—C12—H12B	109.3	C45—C46—H46B	109.5
H12A—C12—H12B	108.0	H46A—C46—H46B	108.0
O1—C13—N2	126.8 (3)	O3—C47—N4	126.3 (2)
O1—C13—C1	126.1 (2)	O3—C47—C35	126.2 (2)
N2—C13—C1	107.1 (2)	N4—C47—C35	107.4 (2)
C19—C14—C15	121.0 (3)	C49—C48—C53	121.8 (3)
C19—C14—N2	109.8 (2)	C49—C48—N4	128.4 (3)
C15—C14—N2	129.2 (3)	C53—C48—N4	109.8 (2)
C16—C15—C14	117.6 (3)	C50—C49—C48	117.4 (3)
C16—C15—H15	121.2	C50—C49—H49	121.3
C14—C15—H15	121.2	C48—C49—H49	121.3
C15—C16—C17	122.4 (3)	C49—C50—C51	121.9 (3)
C15—C16—H16	118.8	C49—C50—H50	119.0
C17—C16—H16	118.8	C51—C50—H50	119.0
C16—C17—C18	119.8 (3)	C52—C51—C50	119.7 (3)
C16—C17—H17	120.1	C52—C51—H51	120.1
C18—C17—H17	120.1	C50—C51—H51	120.1
C19—C18—C17	118.8 (3)	C53—C52—C51	119.2 (3)
C19—C18—H18	120.6	C53—C52—H52	120.4
C17—C18—H18	120.6	C51—C52—H52	120.4
C18—C19—C14	120.3 (2)	C52—C53—C48	119.8 (2)
C18—C19—C1	130.7 (2)	C52—C53—C35	131.2 (2)
C14—C19—C1	108.9 (2)	C48—C53—C35	109.0 (2)
O2—C20—C21	122.5 (2)	O4—C54—C55	122.1 (2)
O2—C20—C2	120.6 (2)	O4—C54—C36	120.5 (2)
C21—C20—C2	116.9 (2)	C55—C54—C36	117.2 (2)
C22—C21—C20	122.8 (2)	C56—C55—C54	122.0 (2)
C22—C21—H21	118.6	C56—C55—H55	119.0
C20—C21—H21	118.6	C54—C55—H55	119.0
C21—C22—C23	127.0 (2)	C55—C56—C57	127.9 (3)
C21—C22—H22	116.5	C55—C56—H56	116.0
C23—C22—H22	116.5	C57—C56—H56	116.0
C28—C23—C24	118.1 (3)	C62—C57—C58	118.0 (3)
C28—C23—C22	119.9 (2)	C62—C57—C56	118.8 (3)
C24—C23—C22	122.0 (2)	C58—C57—C56	123.2 (3)
C25—C24—C23	120.8 (3)	C57—C58—C59	120.4 (3)
C25—C24—H24	119.6	C57—C58—H58	119.8
C23—C24—H24	119.6	C59—C58—H58	119.8
C26—C25—C24	120.4 (3)	C60—C59—C58	120.3 (4)
C26—C25—H25	119.8	C60—C59—H59	119.8
C24—C25—H25	119.8	C58—C59—H59	119.8
C27—C26—C25	119.4 (3)	C61—C60—C59	119.5 (4)
C27—C26—H26	120.3	C61—C60—H60	120.3
C25—C26—H26	120.3	C59—C60—H60	120.3
C26—C27—C28	120.9 (3)	C60—C61—C62	120.6 (4)
C26—C27—H27	119.6	C60—C61—H61	119.7
C28—C27—H27	119.6	C62—C61—H61	119.7
C27—C28—C23	120.5 (3)	C57—C62—C61	121.1 (4)
C27—C28—H28	119.8	C57—C62—H62	119.4
C23—C28—H28	119.8	C61—C62—H62	119.4
C30—C29—C34	118.3 (2)	C68—C63—C64	117.7 (3)
C30—C29—C3	121.5 (2)	C68—C63—C37	120.5 (3)
C34—C29—C3	120.2 (2)	C64—C63—C37	121.7 (2)
C29—C30—C31	120.7 (3)	C65—C64—C63	121.4 (3)
C29—C30—H30	119.7	C65—C64—H64	119.3
C31—C30—H30	119.7	C63—C64—H64	119.3
C32—C31—C30	120.4 (3)	C66—C65—C64	120.2 (4)
C32—C31—H31	119.8	C66—C65—H65	119.9
C30—C31—H31	119.8	C64—C65—H65	119.9
C33—C32—C31	119.3 (3)	C67—C66—C65	119.9 (3)
C33—C32—H32	120.3	C67—C66—H66	120.1
C31—C32—H32	120.3	C65—C66—H66	120.1
C32—C33—C34	120.2 (3)	C66—C67—C68	120.4 (3)
C32—C33—H33	119.9	C66—C67—H67	119.8
C34—C33—H33	119.9	C68—C67—H67	119.8
C29—C34—C33	121.0 (3)	C63—C68—C67	120.3 (4)
C29—C34—H34	119.5	C63—C68—H68	119.8
C33—C34—H34	119.5	C67—C68—H68	119.8

C12—N1—C1—C19	85.8 (3)	C46—N3—C35—C53	−72.9 (3)
C4—N1—C1—C19	−143.9 (2)	C38—N3—C35—C53	159.84 (19)
C12—N1—C1—C13	−29.1 (3)	C46—N3—C35—C47	41.5 (3)
C4—N1—C1—C13	101.2 (2)	C38—N3—C35—C47	−85.7 (2)
C12—N1—C1—C2	−147.5 (2)	C46—N3—C35—C36	158.3 (2)
C4—N1—C1—C2	−17.2 (2)	C38—N3—C35—C36	31.0 (2)
N1—C1—C2—C20	−135.5 (2)	N3—C35—C36—C54	121.4 (2)
C19—C1—C2—C20	−12.2 (3)	C53—C35—C36—C54	−2.9 (3)
C13—C1—C2—C20	103.1 (2)	C47—C35—C36—C54	−117.8 (2)
N1—C1—C2—C3	−8.8 (2)	N3—C35—C36—C37	−6.1 (2)
C19—C1—C2—C3	114.5 (2)	C53—C35—C36—C37	−130.4 (2)
C13—C1—C2—C3	−130.2 (2)	C47—C35—C36—C37	114.7 (2)
C20—C2—C3—C4	157.62 (19)	C54—C36—C37—C63	87.3 (2)
C1—C2—C3—C4	30.4 (2)	C35—C36—C37—C63	−143.5 (2)
C20—C2—C3—C29	−78.0 (3)	C54—C36—C37—C38	−148.1 (2)
C1—C2—C3—C29	154.8 (2)	C35—C36—C37—C38	−18.9 (2)
C12—N1—C4—C3	169.2 (2)	C46—N3—C38—C39	65.6 (3)
C1—N1—C4—C3	36.9 (2)	C35—N3—C38—C39	−166.3 (2)
C12—N1—C4—C5	−68.2 (3)	C46—N3—C38—C37	−171.9 (2)
C1—N1—C4—C5	159.5 (2)	C35—N3—C38—C37	−43.7 (2)
C29—C3—C4—N1	−164.70 (19)	C63—C37—C38—N3	163.32 (19)
C2—C3—C4—N1	−40.6 (2)	C36—C37—C38—N3	37.1 (2)
C29—C3—C4—C5	78.0 (3)	C63—C37—C38—C39	−77.6 (3)
C2—C3—C4—C5	−157.9 (2)	C36—C37—C38—C39	156.2 (2)
N1—C4—C5—C6	51.7 (3)	N3—C38—C39—C40	−44.3 (3)
C3—C4—C5—C6	166.0 (2)	C37—C38—C39—C40	−158.9 (2)
C4—C5—C6—C11	−20.3 (4)	C38—C39—C40—C45	14.0 (4)
C4—C5—C6—C7	159.6 (3)	C38—C39—C40—C41	−166.2 (2)
C11—C6—C7—C8	0.9 (5)	C45—C40—C41—C42	−0.7 (4)
C5—C6—C7—C8	−179.0 (3)	C39—C40—C41—C42	179.4 (3)
C6—C7—C8—C9	−0.9 (5)	C40—C41—C42—C43	−0.2 (5)
C7—C8—C9—C10	1.3 (6)	C41—C42—C43—C44	0.6 (5)
C8—C9—C10—C11	−1.6 (5)	C42—C43—C44—C45	0.0 (5)
C9—C10—C11—C6	1.6 (5)	C41—C40—C45—C44	1.3 (4)
C9—C10—C11—C12	180.0 (3)	C39—C40—C45—C44	−178.9 (3)
C7—C6—C11—C10	−1.2 (4)	C41—C40—C45—C46	179.3 (3)
C5—C6—C11—C10	178.7 (3)	C39—C40—C45—C46	−0.9 (4)
C7—C6—C11—C12	−179.5 (3)	C43—C44—C45—C40	−0.9 (4)
C5—C6—C11—C12	0.3 (4)	C43—C44—C45—C46	−179.0 (3)
C4—N1—C12—C11	47.0 (3)	C38—N3—C46—C45	−50.7 (3)
C1—N1—C12—C11	175.6 (2)	C35—N3—C46—C45	−175.4 (2)
C10—C11—C12—N1	169.0 (3)	C40—C45—C46—N3	18.2 (4)
C6—C11—C12—N1	−12.7 (4)	C44—C45—C46—N3	−163.8 (3)
C14—N2—C13—O1	−178.8 (3)	C48—N4—C47—O3	−178.2 (3)
C14—N2—C13—C1	0.8 (3)	C48—N4—C47—C35	2.8 (3)
N1—C1—C13—O1	−60.6 (3)	N3—C35—C47—O3	57.4 (3)
C19—C1—C13—O1	179.0 (2)	C53—C35—C47—O3	177.8 (3)
C2—C1—C13—O1	54.4 (3)	C36—C35—C47—O3	−56.4 (3)
N1—C1—C13—N2	119.8 (2)	N3—C35—C47—N4	−123.6 (2)
C19—C1—C13—N2	−0.6 (2)	C53—C35—C47—N4	−3.2 (2)
C2—C1—C13—N2	−125.2 (2)	C36—C35—C47—N4	122.6 (2)
C13—N2—C14—C19	−0.6 (3)	C47—N4—C48—C49	178.8 (3)
C13—N2—C14—C15	178.0 (3)	C47—N4—C48—C53	−1.1 (3)
C19—C14—C15—C16	1.0 (5)	C53—C48—C49—C50	0.7 (5)
N2—C14—C15—C16	−177.4 (3)	N4—C48—C49—C50	−179.1 (3)
C14—C15—C16—C17	−0.2 (6)	C48—C49—C50—C51	1.2 (6)
C15—C16—C17—C18	−0.8 (6)	C49—C50—C51—C52	−2.2 (6)
C16—C17—C18—C19	1.1 (5)	C50—C51—C52—C53	1.1 (5)
C17—C18—C19—C14	−0.3 (4)	C51—C52—C53—C48	0.8 (4)
C17—C18—C19—C1	177.0 (3)	C51—C52—C53—C35	179.9 (3)
C15—C14—C19—C18	−0.7 (4)	C49—C48—C53—C52	−1.8 (4)
N2—C14—C19—C18	178.0 (2)	N4—C48—C53—C52	178.1 (2)
C15—C14—C19—C1	−178.6 (3)	C49—C48—C53—C35	179.0 (3)
N2—C14—C19—C1	0.1 (3)	N4—C48—C53—C35	−1.2 (3)
N1—C1—C19—C18	61.0 (3)	N3—C35—C53—C52	−54.7 (3)
C13—C1—C19—C18	−177.2 (3)	C47—C35—C53—C52	−176.6 (3)
C2—C1—C19—C18	−58.0 (3)	C36—C35—C53—C52	65.2 (4)
N1—C1—C19—C14	−121.5 (2)	N3—C35—C53—C48	124.4 (2)
C13—C1—C19—C14	0.3 (2)	C47—C35—C53—C48	2.6 (2)
C2—C1—C19—C14	119.6 (2)	C36—C35—C53—C48	−115.7 (2)
C3—C2—C20—O2	2.9 (3)	C37—C36—C54—O4	−2.0 (3)
C1—C2—C20—O2	124.6 (2)	C35—C36—C54—O4	−125.4 (3)
C3—C2—C20—C21	179.9 (2)	C37—C36—C54—C55	−178.1 (2)
C1—C2—C20—C21	−58.4 (3)	C35—C36—C54—C55	58.5 (3)
O2—C20—C21—C22	−13.8 (4)	O4—C54—C55—C56	14.1 (4)
C2—C20—C21—C22	169.3 (2)	C36—C54—C55—C56	−169.8 (2)
C20—C21—C22—C23	−177.4 (2)	C54—C55—C56—C57	177.0 (3)
C21—C22—C23—C28	178.6 (3)	C55—C56—C57—C62	−172.2 (3)
C21—C22—C23—C24	−1.6 (5)	C55—C56—C57—C58	8.0 (5)
C28—C23—C24—C25	−0.4 (5)	C62—C57—C58—C59	0.8 (5)
C22—C23—C24—C25	179.8 (3)	C56—C57—C58—C59	−179.4 (3)
C23—C24—C25—C26	−0.2 (5)	C57—C58—C59—C60	1.5 (6)
C24—C25—C26—C27	0.7 (5)	C58—C59—C60—C61	−2.9 (7)
C25—C26—C27—C28	−0.5 (5)	C59—C60—C61—C62	2.0 (8)
C26—C27—C28—C23	−0.1 (5)	C58—C57—C62—C61	−1.8 (7)
C24—C23—C28—C27	0.5 (5)	C56—C57—C62—C61	178.4 (4)
C22—C23—C28—C27	−179.7 (3)	C60—C61—C62—C57	0.4 (9)
C4—C3—C29—C30	56.8 (3)	C38—C37—C63—C68	114.1 (3)
C2—C3—C29—C30	−61.0 (3)	C36—C37—C63—C68	−126.8 (3)
C4—C3—C29—C34	−123.3 (3)	C38—C37—C63—C64	−63.6 (3)
C2—C3—C29—C34	118.8 (3)	C36—C37—C63—C64	55.4 (3)
C34—C29—C30—C31	0.4 (4)	C68—C63—C64—C65	−1.2 (4)
C3—C29—C30—C31	−179.7 (3)	C37—C63—C64—C65	176.6 (3)
C29—C30—C31—C32	−0.5 (5)	C63—C64—C65—C66	0.4 (5)
C30—C31—C32—C33	0.0 (5)	C64—C65—C66—C67	0.5 (6)
C31—C32—C33—C34	0.6 (6)	C65—C66—C67—C68	−0.4 (6)
C30—C29—C34—C33	0.2 (5)	C64—C63—C68—C67	1.2 (4)
C3—C29—C34—C33	−179.6 (3)	C37—C63—C68—C67	−176.6 (3)
C32—C33—C34—C29	−0.8 (6)	C66—C67—C68—C63	−0.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	2.19	3.023 (3)	164
N4—H4A···O2ⁱⁱ	0.86	2.23	3.047 (3)	159
C2—H2A···O1	0.98	2.57	3.034 (3)	109
C12—H12A···O1	0.97	2.54	3.201 (3)	125
C37—H37···O4	0.98	2.44	2.784 (3)	100
C56—H56···O4	0.93	2.51	2.830 (4)	101

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x−1/2, −y, z.

Experimental details

Crystal data
Chemical formula	C₃₄H₂₈N₂O₂
M_r	496.58
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	293
a, b, c (Å)	19.301 (4), 14.725 (3), 18.583 (4)
V (Å³)	5281 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.28 × 0.24 × 0.23

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	44375, 6482, 5365
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.122, 1.12
No. of reflections	6482
No. of parameters	685
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PARST (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O4ⁱ	0.86	2.19	3.023 (3)	164.2
N4—H4A···O2ⁱⁱ	0.86	2.23	3.047 (3)	159.3
C2—H2A···O1	0.98	2.57	3.034 (3)	108.8
C12—H12A···O1	0.97	2.54	3.201 (3)	125.4
C37—H37···O4	0.98	2.44	2.784 (3)	100.2
C56—H56···O4	0.93	2.51	2.830 (4)	100.7

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x−1/2, −y, z.

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