5,11,17,23-Tetra­nitro-25,26,27,28-tetra­pentyl­oxycalix[4]arene

Vysotsky, M.O.; Böhmer, V.; Bru Roig, M.; Bolte, M.

doi:10.1107/S1600536805030862

5,11,17,23-Tetranitro-25,26,27,28-tetrapentyloxycalix[4]arene

M. O. Vysotsky, V. Böhmer, M. Bru Roig and M. Bolte

The molecule of the title compound, C₄₈H₆₀N₄O₁₂, is located on a crystallographic twofold rotation axis. It is found in the typical pinched cone conformation. The dihedral angles between the reference plane (defined by the C atoms of the methylene bridges) and the benzene rings are 83.33 (6) and 141.61 (5)°.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030862/lh6509sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030862/lh6509Isup2.hkl Contains datablock I

CCDC reference: 287662

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R factor = 0.082
wR factor = 0.247
Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       5.71 Ratio

Author Response: The pentyl chain is slightly disordered.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       5.11 Ratio

Author Response: The pentyl chain is slightly disordered.

PLAT241_ALERT_2_A Check High      Ueq as Compared to Neighbors for       C224

Author Response: The atom shows an elongated ellipsoid which is a sign of disorder, but refining it on two split positions, did not improve the refinement.

PLAT242_ALERT_2_A Check Low       Ueq as Compared to Neighbors for       C223

Author Response: This happens because the displacement parameter of C224 bigger than usual.


Alert level B
DIFMN02_ALERT_2_B  The minimum difference density is < -0.1*ZMAX*1.00
            _refine_diff_density_min given =     -0.872
            Test value =     -0.800
PLAT098_ALERT_2_B Minimum (Negative) Residual Density ............      -0.87 e/A   3
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C223   -   C224    ..       7.59 su
PLAT360_ALERT_2_B Short  C(sp3)-C(sp3) Bond  C223   -   C224   ...       1.27 Ang.

Alert level C
DIFMN03_ALERT_1_C  The minimum difference density is < -0.1*ZMAX*0.75
            The relevant atom site should be identified.
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.714
            Test value =      0.600
DIFMX02_ALERT_1_C  The maximum difference density is > 0.1*ZMAX*0.75
            The relevant atom site should be identified.
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.71 e/A   3
PLAT213_ALERT_2_C Atom C224    has ADP max/min Ratio .............       3.30 prolat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C123

Author Response: This happens because the displacement parameter of C224 bigger than usual.

PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C221   -   C222   ...       1.41 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H1A    ..  H22B    ..       1.97 Ang.

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

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

Comment top

5,11,17,23-Tetranitro-25,26,27,28-tetrapentyloxycalix[4]arene, (I), was prepared by ipso-nitration of the corresponding tetrapentyloxycalix[4]arene with four tert-butyl groups at the wide rim (Jakobi et al., 1996). It can be easily reduced to the tetraamino derivative, (II) (see scheme) (Jakobi et al., 1996), the starting material for the synthesis of various derivatives, e.g. tetra-CMPO and tetraurea-calix[4]arenes CMPO (carbamoylmethylphosphineoxide) calix[4]arenes are highly efficient extractants for lanthanides and actinides (Arnaud-Neu et al., 1996); tetraurea-calix[4]arenes are able to form hydrogen-bonded dimeric capsules in apolar aprotic solvents (Rebek, 2000) via self-assembly. Both areas have been intensively studied during the last decade.

A perspective view of the title compound is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Strructural Database, Version 1.6 plus three updates; Mogul Version 1.0; Allen, 2002).

The molecule adopts the typical pinched cone conformation of tetraether derivatives. The reference plane of the calixarene, defined as the mean plane of the bridging C atoms [here C1, C2, C1ⁱ and C2ⁱ; symmetry code: (i) 1 − x, y, 3/2 − z], is almost planar (r.m.s. deviation = 0.0536 Å); the rings C11–C16 and C21–C26 subtend angles of 83.33 (6) and 141.61 (5)°, respectively, with this plane. Thus, the former rings are slightly bent inwards, whereas the others are clearly bent outwards. The rings C11–C16 and C11ⁱ–C16ⁱ are almost coplanar [13.34 (14)°], whereas the other two are almost perpendicular to each other [75.94 (7)°]. In Table 1, the torsion angles describing the orientation of the aromatic rings respective to the reference plane are listed.

Both pentyloxy chains adopt all trans conformations.

Experimental top

The title compound was synthesized according to Jakobi et al. (1996). The single crystals were obtained by slow evaporation from a solution in chloroform/methanol.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991) and Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. Unlabelled atoms are generated using the symmetry code (−x + 1, y, −z + 3/2).
	Fig. 2. Space-filling model of the title compound showing the pinched cone conformation; H atoms have been omitted for clarity.

5,11,17,23-Tetranitro-25,26,27,28-tetrapentyloxycalix[4]arene top

Crystal data top

C₄₈H₆₀N₄O₁₂	F(000) = 1888
M_r = 885.00	D_x = 1.231 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 31383 reflections
a = 22.5587 (11) Å	θ = 1.9–25.2°
b = 11.8751 (4) Å	µ = 0.09 mm⁻¹
c = 19.2336 (11) Å	T = 173 K
β = 112.057 (4)°	Block, light yellow
V = 4775.3 (4) Å³	0.38 × 0.35 × 0.29 mm
Z = 4

Data collection top

Stoe IPDS-II two-circle diffractometer	3906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.065
Graphite monochromator	θ_max = 26.4°, θ_min = 2.0°
ω scans	h = −28→28
39302 measured reflections	k = −14→14
4859 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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.247	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1304P)² + 6.4471P] where P = (F_o² + 2F_c²)/3
4859 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.87 e Å⁻³

Crystal data top

C₄₈H₆₀N₄O₁₂	V = 4775.3 (4) Å³
M_r = 885.00	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.5587 (11) Å	µ = 0.09 mm⁻¹
b = 11.8751 (4) Å	T = 173 K
c = 19.2336 (11) Å	0.38 × 0.35 × 0.29 mm
β = 112.057 (4)°

Data collection top

Stoe IPDS-II two-circle diffractometer	3906 reflections with I > 2σ(I)
39302 measured reflections	R_int = 0.065
4859 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.247	H-atom parameters constrained
S = 1.07	Δρ_max = 0.71 e Å⁻³
4859 reflections	Δρ_min = −0.87 e Å⁻³
289 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
C1	0.32765 (12)	0.1913 (3)	0.67257 (16)	0.0509 (6)
H1A	0.3291	0.2734	0.6646	0.061*
H1B	0.2835	0.1649	0.6444	0.061*
C11	0.37390 (11)	0.1311 (2)	0.64399 (14)	0.0445 (6)
C12	0.41166 (11)	0.1901 (2)	0.61240 (13)	0.0435 (6)
C13	0.45786 (11)	0.1359 (2)	0.59221 (13)	0.0417 (5)
C14	0.46319 (12)	0.0192 (2)	0.59983 (14)	0.0464 (6)
H14	0.4936	−0.0202	0.5857	0.056*
C15	0.42435 (13)	−0.0385 (2)	0.62775 (15)	0.0498 (6)
C16	0.38093 (13)	0.0154 (2)	0.65177 (15)	0.0505 (6)
H16	0.3563	−0.0266	0.6733	0.061*
O12	0.40590 (8)	0.30550 (15)	0.60494 (11)	0.0500 (5)
C121	0.35507 (14)	0.3428 (3)	0.53705 (17)	0.0618 (8)
H12A	0.3130	0.3195	0.5373	0.074*
H12B	0.3603	0.3094	0.4925	0.074*
C122	0.35903 (16)	0.4697 (3)	0.5347 (2)	0.0676 (9)
H12C	0.4014	0.4916	0.5348	0.081*
H12D	0.3550	0.5016	0.5803	0.081*
C123	0.30686 (16)	0.5185 (3)	0.4656 (2)	0.0777 (11)
H12E	0.3093	0.4820	0.4204	0.093*
H12F	0.2647	0.4998	0.4674	0.093*
C124	0.3111 (2)	0.6451 (4)	0.4579 (4)	0.121 (2)
H12G	0.3069	0.6820	0.5020	0.145*
H12H	0.3537	0.6643	0.4577	0.145*
C125	0.2608 (3)	0.6902 (6)	0.3882 (5)	0.183 (4)
H12I	0.2659	0.7719	0.3858	0.275*
H12J	0.2184	0.6735	0.3887	0.275*
H12K	0.2650	0.6548	0.3442	0.275*
N15	0.42950 (14)	−0.1620 (2)	0.63294 (17)	0.0670 (7)
O151	0.40652 (19)	−0.2114 (2)	0.6721 (2)	0.1086 (12)
O152	0.45627 (15)	−0.2101 (2)	0.59706 (17)	0.0847 (8)
C2	0.50429 (12)	0.2003 (2)	0.56618 (15)	0.0476 (6)
H2A	0.4970	0.1799	0.5137	0.057*
H2B	0.4972	0.2823	0.5682	0.057*
C21	0.57228 (12)	0.1709 (2)	0.61694 (14)	0.0431 (6)
C22	0.59615 (11)	0.2081 (2)	0.69183 (15)	0.0421 (6)
C23	0.65393 (11)	0.1671 (2)	0.74445 (15)	0.0452 (6)
C24	0.69011 (12)	0.0951 (2)	0.71960 (16)	0.0487 (6)
H24	0.7298	0.0671	0.7538	0.058*
C25	0.66815 (12)	0.0642 (2)	0.64445 (16)	0.0479 (6)
C26	0.60950 (13)	0.0996 (2)	0.59307 (15)	0.0471 (6)
H26	0.5951	0.0754	0.5423	0.057*
O22	0.55846 (8)	0.27841 (15)	0.71432 (11)	0.0489 (5)
C221	0.58061 (18)	0.3928 (3)	0.7330 (2)	0.0767 (10)
H22A	0.5601	0.4252	0.7658	0.092*
H22B	0.6274	0.3917	0.7618	0.092*
C222	0.5676 (3)	0.4632 (3)	0.6696 (3)	0.0917 (13)
H22C	0.5209	0.4635	0.6405	0.110*
H22D	0.5886	0.4313	0.6372	0.110*
C223	0.5905 (3)	0.5854 (3)	0.6897 (3)	0.0910 (13)
H22E	0.5594	0.6220	0.7076	0.109*
H22F	0.6315	0.5814	0.7334	0.109*
C224	0.5992 (6)	0.6525 (5)	0.6433 (7)	0.238 (6)
H22G	0.5576	0.6584	0.6006	0.286*
H22H	0.6287	0.6140	0.6238	0.286*
C225	0.6240 (3)	0.7722 (4)	0.6620 (4)	0.1162 (18)
H22I	0.6253	0.8086	0.6168	0.174*
H22J	0.6672	0.7705	0.7008	0.174*
H22K	0.5956	0.8147	0.6804	0.174*
N25	0.70763 (12)	−0.0104 (2)	0.61853 (16)	0.0589 (6)
O251	0.68793 (13)	−0.0370 (2)	0.55225 (14)	0.0816 (8)
O252	0.75841 (11)	−0.0432 (2)	0.66435 (15)	0.0807 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0357 (12)	0.0598 (16)	0.0562 (15)	0.0079 (11)	0.0161 (11)	0.0108 (12)
C11	0.0341 (11)	0.0521 (14)	0.0424 (12)	0.0024 (10)	0.0085 (10)	0.0058 (10)
C12	0.0367 (12)	0.0459 (14)	0.0413 (12)	0.0029 (10)	0.0071 (10)	0.0058 (10)
C13	0.0386 (12)	0.0459 (13)	0.0362 (11)	−0.0004 (10)	0.0089 (9)	0.0036 (10)
C14	0.0461 (13)	0.0467 (14)	0.0454 (13)	0.0017 (11)	0.0161 (11)	−0.0008 (10)
C15	0.0528 (14)	0.0447 (14)	0.0510 (14)	−0.0006 (11)	0.0183 (12)	0.0033 (11)
C16	0.0478 (14)	0.0532 (15)	0.0509 (14)	−0.0017 (11)	0.0190 (12)	0.0071 (12)
O12	0.0439 (9)	0.0456 (10)	0.0565 (11)	0.0089 (8)	0.0142 (8)	0.0127 (8)
C121	0.0536 (16)	0.0645 (19)	0.0586 (17)	0.0106 (14)	0.0113 (13)	0.0227 (14)
C122	0.0585 (17)	0.0594 (19)	0.078 (2)	0.0069 (14)	0.0179 (16)	0.0184 (16)
C123	0.0575 (18)	0.074 (2)	0.092 (2)	0.0012 (16)	0.0176 (18)	0.0384 (19)
C124	0.077 (3)	0.081 (3)	0.170 (5)	−0.014 (2)	0.008 (3)	0.063 (3)
C125	0.103 (4)	0.140 (5)	0.247 (8)	−0.021 (4)	−0.004 (5)	0.132 (6)
N15	0.0801 (18)	0.0478 (14)	0.0839 (19)	0.0009 (13)	0.0429 (16)	0.0094 (13)
O151	0.153 (3)	0.0590 (15)	0.160 (3)	0.0089 (16)	0.111 (3)	0.0289 (17)
O152	0.114 (2)	0.0500 (13)	0.113 (2)	0.0026 (13)	0.0684 (18)	−0.0037 (13)
C2	0.0448 (13)	0.0487 (14)	0.0510 (14)	0.0028 (11)	0.0199 (11)	0.0083 (11)
C21	0.0414 (12)	0.0390 (12)	0.0524 (14)	−0.0024 (10)	0.0215 (11)	0.0051 (10)
C22	0.0377 (12)	0.0353 (12)	0.0568 (14)	−0.0056 (9)	0.0218 (11)	−0.0026 (10)
C23	0.0373 (12)	0.0438 (13)	0.0567 (14)	−0.0083 (10)	0.0200 (11)	−0.0030 (11)
C24	0.0375 (12)	0.0487 (15)	0.0610 (16)	0.0001 (10)	0.0198 (11)	0.0012 (12)
C25	0.0447 (13)	0.0436 (14)	0.0608 (16)	0.0014 (11)	0.0260 (12)	−0.0025 (11)
C26	0.0479 (13)	0.0457 (14)	0.0518 (14)	−0.0040 (11)	0.0233 (11)	−0.0015 (11)
O22	0.0423 (9)	0.0418 (10)	0.0627 (11)	−0.0001 (7)	0.0199 (8)	−0.0094 (8)
C221	0.072 (2)	0.0505 (18)	0.096 (3)	0.0002 (15)	0.0189 (19)	−0.0095 (17)
C222	0.124 (4)	0.064 (2)	0.116 (3)	0.004 (2)	0.078 (3)	0.001 (2)
C223	0.124 (4)	0.058 (2)	0.099 (3)	−0.014 (2)	0.051 (3)	−0.006 (2)
C224	0.367 (13)	0.056 (3)	0.461 (16)	−0.033 (5)	0.349 (14)	−0.028 (5)
C225	0.147 (5)	0.058 (2)	0.167 (5)	−0.024 (3)	0.085 (4)	0.005 (3)
N25	0.0522 (14)	0.0556 (14)	0.0735 (17)	0.0046 (11)	0.0288 (13)	−0.0062 (12)
O251	0.0786 (16)	0.101 (2)	0.0718 (15)	0.0199 (14)	0.0356 (13)	−0.0180 (13)
O252	0.0576 (13)	0.0856 (17)	0.0925 (17)	0.0249 (12)	0.0207 (13)	−0.0158 (14)

Geometric parameters (Å, º) top

C1—C23ⁱ	1.518 (4)	C2—C21	1.517 (4)
C1—C11	1.527 (4)	C2—H2A	0.9900
C1—H1A	0.9900	C2—H2B	0.9900
C1—H1B	0.9900	C21—C26	1.386 (4)
C11—C16	1.385 (4)	C21—C22	1.406 (4)
C11—C12	1.405 (4)	C22—O22	1.373 (3)
C12—O12	1.379 (3)	C22—C23	1.403 (4)
C12—C13	1.399 (4)	C23—C24	1.385 (4)
C13—C14	1.393 (4)	C23—C1ⁱ	1.518 (4)
C13—C2	1.525 (3)	C24—C25	1.390 (4)
C14—C15	1.371 (4)	C24—H24	0.9500
C14—H14	0.9500	C25—C26	1.386 (4)
C15—C16	1.386 (4)	C25—N25	1.469 (3)
C15—N15	1.472 (4)	C26—H26	0.9500
C16—H16	0.9500	O22—C221	1.445 (4)
O12—C121	1.446 (3)	C221—C222	1.414 (6)
C121—C122	1.511 (5)	C221—H22A	0.9900
C121—H12A	0.9900	C221—H22B	0.9900
C121—H12B	0.9900	C222—C223	1.541 (6)
C122—C123	1.522 (4)	C222—H22C	0.9900
C122—H12C	0.9900	C222—H22D	0.9900
C122—H12D	0.9900	C223—C224	1.267 (8)
C123—C124	1.517 (6)	C223—H22E	0.9900
C123—H12E	0.9900	C223—H22F	0.9900
C123—H12F	0.9900	C224—C225	1.521 (7)
C124—C125	1.493 (7)	C224—H22G	0.9900
C124—H12G	0.9900	C224—H22H	0.9900
C124—H12H	0.9900	C225—H22I	0.9800
C125—H12I	0.9800	C225—H22J	0.9800
C125—H12J	0.9800	C225—H22K	0.9800
C125—H12K	0.9800	N25—O252	1.217 (3)
N15—O151	1.214 (4)	N25—O251	1.223 (3)
N15—O152	1.216 (4)

C23ⁱ—C1—C11	109.6 (2)	C21—C2—C13	109.0 (2)
C23ⁱ—C1—H1A	109.7	C21—C2—H2A	109.9
C11—C1—H1A	109.7	C13—C2—H2A	109.9
C23ⁱ—C1—H1B	109.8	C21—C2—H2B	109.9
C11—C1—H1B	109.7	C13—C2—H2B	109.9
H1A—C1—H1B	108.2	H2A—C2—H2B	108.3
C16—C11—C12	118.6 (2)	C26—C21—C22	119.0 (2)
C16—C11—C1	119.4 (2)	C26—C21—C2	121.3 (2)
C12—C11—C1	121.9 (2)	C22—C21—C2	119.5 (2)
O12—C12—C13	118.6 (2)	O22—C22—C23	120.1 (2)
O12—C12—C11	119.5 (2)	O22—C22—C21	118.0 (2)
C13—C12—C11	121.8 (2)	C23—C22—C21	121.6 (2)
C14—C13—C12	118.2 (2)	C24—C23—C22	118.2 (2)
C14—C13—C2	119.4 (2)	C24—C23—C1ⁱ	121.0 (2)
C12—C13—C2	122.4 (2)	C22—C23—C1ⁱ	120.4 (2)
C15—C14—C13	119.7 (2)	C23—C24—C25	119.7 (2)
C15—C14—H14	120.1	C23—C24—H24	120.1
C13—C14—H14	120.1	C25—C24—H24	120.1
C14—C15—C16	122.4 (3)	C26—C25—C24	122.2 (2)
C14—C15—N15	118.6 (3)	C26—C25—N25	118.6 (2)
C16—C15—N15	119.0 (2)	C24—C25—N25	119.2 (2)
C11—C16—C15	119.2 (2)	C25—C26—C21	118.9 (2)
C11—C16—H16	120.4	C25—C26—H26	120.5
C15—C16—H16	120.4	C21—C26—H26	120.5
C12—O12—C121	114.2 (2)	C22—O22—C221	116.9 (2)
O12—C121—C122	107.2 (3)	C222—C221—O22	113.6 (3)
O12—C121—H12A	110.3	C222—C221—H22A	108.8
C122—C121—H12A	110.3	O22—C221—H22A	108.8
O12—C121—H12B	110.3	C222—C221—H22B	108.8
C122—C121—H12B	110.3	O22—C221—H22B	108.8
H12A—C121—H12B	108.5	H22A—C221—H22B	107.7
C121—C122—C123	111.8 (3)	C221—C222—C223	113.5 (4)
C121—C122—H12C	109.3	C221—C222—H22C	108.9
C123—C122—H12C	109.3	C223—C222—H22C	108.9
C121—C122—H12D	109.3	C221—C222—H22D	108.9
C123—C122—H12D	109.3	C223—C222—H22D	108.9
H12C—C122—H12D	107.9	H22C—C222—H22D	107.7
C124—C123—C122	114.0 (3)	C224—C223—C222	122.8 (6)
C124—C123—H12E	108.8	C224—C223—H22E	106.6
C122—C123—H12E	108.8	C222—C223—H22E	106.6
C124—C123—H12F	108.8	C224—C223—H22F	106.6
C122—C123—H12F	108.8	C222—C223—H22F	106.6
H12E—C123—H12F	107.7	H22E—C223—H22F	106.6
C125—C124—C123	112.9 (5)	C223—C224—C225	124.2 (9)
C125—C124—H12G	109.0	C223—C224—H22G	106.3
C123—C124—H12G	109.0	C225—C224—H22G	106.3
C125—C124—H12H	109.0	C223—C224—H22H	106.3
C123—C124—H12H	109.0	C225—C224—H22H	106.3
H12G—C124—H12H	107.8	H22G—C224—H22H	106.4
C124—C125—H12I	109.5	C224—C225—H22I	109.5
C124—C125—H12J	109.5	C224—C225—H22J	109.5
H12I—C125—H12J	109.5	H22I—C225—H22J	109.5
C124—C125—H12K	109.5	C224—C225—H22K	109.5
H12I—C125—H12K	109.5	H22I—C225—H22K	109.5
H12J—C125—H12K	109.5	H22J—C225—H22K	109.5
O151—N15—O152	123.0 (3)	O252—N25—O251	123.1 (3)
O151—N15—C15	118.8 (3)	O252—N25—C25	118.2 (3)
O152—N15—C15	118.2 (3)	O251—N25—C25	118.7 (2)

C23ⁱ—C1—C11—C16	57.5 (3)	C12—C13—C2—C21	122.7 (2)
C23ⁱ—C1—C11—C12	−120.1 (3)	C13—C2—C21—C26	105.0 (3)
C22ⁱ—C23ⁱ—C1—C11	66.6 (3)	C13—C2—C21—C22	−69.1 (3)
C16—C11—C12—O12	−179.3 (2)	C26—C21—C22—O22	−179.9 (2)
C1—C11—C12—O12	−1.7 (3)	C2—C21—C22—O22	−5.6 (3)
C16—C11—C12—C13	−3.1 (4)	C26—C21—C22—C23	−5.8 (4)
C1—C11—C12—C13	174.4 (2)	C2—C21—C22—C23	168.5 (2)
O12—C12—C13—C14	−179.9 (2)	O22—C22—C23—C24	179.2 (2)
C11—C12—C13—C14	3.9 (3)	C21—C22—C23—C24	5.2 (4)
O12—C12—C13—C2	3.3 (3)	O22—C22—C23—C1ⁱ	5.6 (4)
C11—C12—C13—C2	−172.9 (2)	C21—C22—C23—C1ⁱ	−168.4 (2)
C12—C13—C14—C15	−1.1 (4)	C22—C23—C24—C25	−1.1 (4)
C2—C13—C14—C15	175.8 (2)	C1ⁱ—C23—C24—C25	172.5 (2)
C13—C14—C15—C16	−2.5 (4)	C23—C24—C25—C26	−2.4 (4)
C13—C14—C15—N15	178.0 (2)	C23—C24—C25—N25	178.8 (2)
C12—C11—C16—C15	−0.5 (4)	C24—C25—C26—C21	1.8 (4)
C1—C11—C16—C15	−178.1 (2)	N25—C25—C26—C21	−179.3 (2)
C14—C15—C16—C11	3.4 (4)	C22—C21—C26—C25	2.2 (4)
N15—C15—C16—C11	−177.2 (3)	C2—C21—C26—C25	−172.0 (2)
C13—C12—O12—C121	98.2 (3)	C23—C22—O22—C221	73.3 (3)
C11—C12—O12—C121	−85.5 (3)	C21—C22—O22—C221	−112.4 (3)
C12—O12—C121—C122	−175.4 (2)	C22—O22—C221—C222	80.1 (4)
O12—C121—C122—C123	−179.3 (3)	O22—C221—C222—C223	179.3 (3)
C121—C122—C123—C124	−176.4 (4)	C221—C222—C223—C224	160.5 (7)
C122—C123—C124—C125	178.0 (5)	C222—C223—C224—C225	−177.7 (7)
C14—C15—N15—O151	163.8 (3)	C26—C25—N25—O252	−178.4 (3)
C16—C15—N15—O151	−15.7 (5)	C24—C25—N25—O252	0.5 (4)
C14—C15—N15—O152	−16.8 (4)	C26—C25—N25—O251	1.3 (4)
C16—C15—N15—O152	163.7 (3)	C24—C25—N25—O251	−179.8 (3)
C14—C13—C2—C21	−54.1 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₄₈H₆₀N₄O₁₂
M_r	885.00
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	22.5587 (11), 11.8751 (4), 19.2336 (11)
β (°)	112.057 (4)
V (Å³)	4775.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.38 × 0.35 × 0.29

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	39302, 4859, 3906
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.082, 0.247, 1.07
No. of reflections	4859
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.87

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991) and Mercury (Version 1.4; Bruno et al., 2002), SHELXL97 and PLATON (Spek, 2003).

Selected torsion angles (º) top

C23ⁱ—C1—C11—C12	−120.1 (3)	C12—C13—C2—C21	122.7 (2)
C22ⁱ—C23ⁱ—C1—C11	66.6 (3)	C13—C2—C21—C22	−69.1 (3)