Diethyl 2,6-diethyl-4,8-dioxo-2,3,6,7-tetra­hydro-1H,5H-2,3a,4a,6,7a,8a-hexa­aza­cyclo­penta­[def]fluorene-8b,8c-dicarboxyl­ate

Cao, L.-P.; Wang, Y.-Z.; Gao, M.

doi:10.1107/S1600536807031819

Diethyl 2,6-diethyl-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-8b,8c-dicarboxylate

The title compound, C₁₈H₂₈N₆O₆, is a derivative of glycoluril, with two ethyl acetate substituents on the convex face of the glycoluril system. Two equivalent six-membered rings bind the N atoms from separate rings of the glycoluril unit to form the flexible sidewalls of a molecular clip. One N atom from each ring carries an ethyl substituent. The crystal packing is stabilized by non-classical C—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031819/cv2270sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031819/cv2270Isup2.hkl Contains datablock I

CCDC reference: 657663

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
R factor = 0.068
wR factor = 0.190
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.71 Ratio

Alert level C
DIFMX01_ALERT_2_C  The maximum difference density is > 0.1*ZMAX*0.75
            _refine_diff_density_max given =      0.762
            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.
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       2.00 Ratio
PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............       0.76 e/A   
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C3      ..       5.69 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

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

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 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
   0 ALERT type 5 Informative message, check

Comment top

In 1905, Behrend reported that the condensation of glycoluril and formadehyde in dilute H_Cl yielded an insoluble polymeric material now known as Behrend's polymer (Behrend et al., 1905). After 76 years, the molecular structure (obtained by heating Behrend's polymer in H₂S_O4) was disclosed by Mock and co-workers who named it cucurbituril (Freeman et al., 1981). Glycoluril and its derivatives have during the past two decades established an impressive career as building block for supramolecular chemistry (Freeman et al., 1981; Rebek, 2005; Rowan et al., 1999; Wu et al., 2002). As a part of our ongoing investigation into glycoluril derivatives (Li et al., 2006), we report here the structure of the title compound (I) (Fig. 1).

The molecular structure of (I) is shown in Fig. 1. It has four fused rings - two imidazole and two triazinane rings, respectively. The crystal packing is stabilized by intermolecular non-classical C—H···O hydrogen bonds (Table 1).

Related literature top

For preparation of the title compound, see: Li et al. (2006). For general background regarding glycoluril and its derivatives, see: Behrend et al. (1905); Freeman et al. (1981); Rebek (2005); Rowan et al. (1999); Wu et al. (2002).

Experimental top

The title compound was synthesized according to the procedure of Li et al. (2006) in 10% isolated yield. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methaol solution in ratio of 20:1 at 293 K.

Structure description top

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: PLATON.

Figures top

Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented by spheres of arbitrary radius.

Diethyl 2,6-diethyl-4,8-dioxo-2,3,6,7-tetrahydro-1H,5H-2,3a,4a,6,7a,8a-ηexaazacyclopenta[def]fluorene-8 b,8c-dicarboxylate top

Crystal data top

C₁₈H₂₈N₆O₆	F(000) = 1808
M_r = 424.47	D_x = 1.352 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3350 reflections
a = 20.3689 (13) Å	θ = 2.5–22.8°
b = 7.8804 (5) Å	µ = 0.10 mm⁻¹
c = 25.9921 (16) Å	T = 292 K
β = 91.697 (1)°	Block, colourless
V = 4170.3 (5) Å³	0.30 × 0.20 × 0.20 mm
Z = 8

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2901 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.031
Graphite monochromator	θ_max = 25.0°, θ_min = 2.0°
φ and ω scans	h = −24→20
13315 measured reflections	k = −9→9
3662 independent reflections	l = −30→30

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0969P)² + 6.5727P] where P = (F_o² + 2F_c²)/3
3662 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

C₁₈H₂₈N₆O₆	V = 4170.3 (5) Å³
M_r = 424.47	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 20.3689 (13) Å	µ = 0.10 mm⁻¹
b = 7.8804 (5) Å	T = 292 K
c = 25.9921 (16) Å	0.30 × 0.20 × 0.20 mm
β = 91.697 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	2901 reflections with I > 2σ(I)
13315 measured reflections	R_int = 0.031
3662 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.04	Δρ_max = 0.76 e Å⁻³
3662 reflections	Δρ_min = −0.50 e Å⁻³
275 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	0.5192 (2)	0.4727 (9)	0.3310 (2)	0.115 (2)
H1A	0.5198	0.3943	0.3027	0.172*
H1B	0.5529	0.4427	0.3559	0.172*
H1C	0.5270	0.5855	0.3186	0.172*
C2	0.45446 (17)	0.4660 (5)	0.35513 (14)	0.0613 (9)
H2A	0.4509	0.3599	0.3738	0.074*
H2B	0.4517	0.5578	0.3799	0.074*
C3	0.39338 (16)	0.6401 (4)	0.29128 (11)	0.0521 (8)
H3A	0.3668	0.6243	0.2601	0.062*
H3B	0.4368	0.6758	0.2813	0.062*
C4	0.33661 (15)	0.4321 (4)	0.33911 (11)	0.0459 (7)
H4A	0.3429	0.3321	0.3605	0.055*
H4B	0.3063	0.4023	0.3111	0.055*
C5	0.39979 (14)	0.8907 (4)	0.35146 (11)	0.0429 (7)
C6	0.31809 (13)	0.5820 (3)	0.42271 (10)	0.0374 (6)
C7	0.30321 (13)	0.7315 (3)	0.34576 (10)	0.0344 (6)
C8	0.24532 (14)	0.7504 (4)	0.30633 (11)	0.0417 (7)
C9	0.14594 (14)	0.6412 (4)	0.27281 (13)	0.0526 (8)
H9A	0.1584	0.6089	0.2384	0.063*
H9B	0.1296	0.7569	0.2716	0.063*
C10	0.09497 (19)	0.5268 (6)	0.29102 (18)	0.0849 (13)
H10A	0.1120	0.4134	0.2932	0.127*
H10B	0.0579	0.5292	0.2674	0.127*
H10C	0.0816	0.5629	0.3244	0.127*
C11	0.30001 (13)	0.8576 (3)	0.39207 (10)	0.0363 (6)
C12	0.23560 (15)	0.9608 (4)	0.39291 (12)	0.0462 (7)
C13	0.1855 (2)	1.2302 (6)	0.3808 (2)	0.0906 (14)
H13A	0.1944	1.3313	0.3610	0.109*
H13B	0.1498	1.1688	0.3637	0.109*
C14	0.1675 (3)	1.2762 (8)	0.4321 (3)	0.128 (2)
H14A	0.1501	1.1787	0.4491	0.191*
H14B	0.1348	1.3639	0.4303	0.191*
H14C	0.2055	1.3168	0.4510	0.191*
C15	0.38474 (15)	1.0349 (4)	0.43596 (12)	0.0472 (7)
H15A	0.4276	1.0836	0.4299	0.057*
H15B	0.3559	1.1264	0.4459	0.057*
C16	0.32934 (15)	0.8260 (4)	0.48422 (11)	0.0470 (7)
H16A	0.2969	0.9055	0.4963	0.056*
H16B	0.3354	0.7390	0.5103	0.056*
C17	0.44876 (16)	0.8037 (4)	0.47574 (13)	0.0542 (8)
H17A	0.4868	0.8714	0.4674	0.065*
H17B	0.4417	0.7211	0.4485	0.065*
C18	0.4623 (2)	0.7123 (5)	0.52582 (16)	0.0754 (11)
H18A	0.4609	0.7917	0.5538	0.113*
H18B	0.5050	0.6608	0.5253	0.113*
H18C	0.4296	0.6261	0.5303	0.113*
N1	0.39898 (13)	0.4795 (3)	0.31793 (9)	0.0498 (7)
N2	0.36403 (11)	0.7760 (3)	0.32213 (8)	0.0406 (6)
N3	0.30724 (11)	0.5667 (3)	0.36995 (8)	0.0359 (5)
N4	0.35879 (11)	0.9595 (3)	0.38760 (9)	0.0393 (6)
N5	0.30415 (11)	0.7466 (3)	0.43647 (8)	0.0372 (5)
N6	0.39087 (12)	0.9148 (3)	0.47816 (9)	0.0469 (6)
O1	0.45657 (11)	0.9299 (3)	0.34542 (9)	0.0636 (7)
O2	0.33390 (12)	0.4685 (3)	0.45184 (8)	0.0536 (6)
O3	0.24162 (13)	0.8728 (4)	0.27949 (11)	0.0837 (9)
O4	0.20263 (9)	0.6294 (2)	0.30835 (7)	0.0441 (5)
O5	0.18423 (11)	0.8918 (3)	0.39870 (10)	0.0624 (7)
O6	0.24504 (12)	1.1218 (3)	0.38462 (13)	0.0812 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.056 (3)	0.201 (6)	0.087 (3)	0.026 (3)	−0.002 (2)	0.011 (4)
C2	0.056 (2)	0.072 (2)	0.055 (2)	0.0107 (17)	−0.0103 (16)	−0.0021 (17)
C3	0.0484 (18)	0.071 (2)	0.0370 (16)	0.0034 (15)	0.0055 (13)	−0.0026 (15)
C4	0.0529 (18)	0.0413 (15)	0.0428 (16)	0.0034 (13)	−0.0097 (14)	−0.0052 (13)
C5	0.0364 (16)	0.0516 (17)	0.0405 (15)	−0.0100 (13)	−0.0011 (12)	0.0145 (13)
C6	0.0384 (15)	0.0360 (14)	0.0377 (15)	−0.0082 (12)	−0.0034 (12)	0.0062 (12)
C7	0.0345 (14)	0.0342 (13)	0.0344 (14)	−0.0035 (11)	−0.0032 (11)	0.0034 (11)
C8	0.0417 (16)	0.0445 (16)	0.0384 (15)	−0.0039 (13)	−0.0077 (12)	0.0089 (13)
C9	0.0371 (16)	0.0630 (19)	0.0566 (19)	0.0025 (14)	−0.0149 (14)	−0.0001 (15)
C10	0.048 (2)	0.103 (3)	0.102 (3)	−0.021 (2)	−0.016 (2)	0.015 (3)
C11	0.0331 (14)	0.0333 (13)	0.0424 (15)	−0.0056 (11)	−0.0004 (11)	0.0038 (11)
C12	0.0420 (17)	0.0380 (15)	0.0581 (19)	−0.0074 (13)	−0.0053 (14)	−0.0002 (13)
C13	0.080 (3)	0.068 (3)	0.124 (4)	0.010 (2)	−0.005 (3)	0.018 (3)
C14	0.127 (5)	0.117 (4)	0.140 (5)	0.008 (4)	0.030 (4)	−0.047 (4)
C15	0.0483 (18)	0.0383 (15)	0.0544 (18)	−0.0111 (13)	−0.0062 (14)	−0.0022 (13)
C16	0.0562 (19)	0.0498 (17)	0.0351 (15)	−0.0069 (14)	0.0009 (13)	−0.0058 (13)
C17	0.0535 (19)	0.0525 (18)	0.0559 (19)	−0.0064 (15)	−0.0116 (15)	−0.0058 (15)
C18	0.070 (2)	0.074 (2)	0.081 (3)	−0.010 (2)	−0.026 (2)	0.017 (2)
N1	0.0513 (16)	0.0541 (15)	0.0435 (14)	0.0085 (12)	−0.0034 (12)	−0.0020 (12)
N2	0.0381 (13)	0.0480 (13)	0.0356 (12)	−0.0042 (10)	−0.0001 (10)	0.0049 (10)
N3	0.0406 (13)	0.0338 (11)	0.0327 (12)	−0.0043 (9)	−0.0064 (9)	0.0023 (9)
N4	0.0376 (13)	0.0367 (12)	0.0433 (13)	−0.0089 (10)	−0.0043 (10)	0.0037 (10)
N5	0.0426 (13)	0.0362 (12)	0.0330 (12)	−0.0069 (10)	0.0022 (10)	0.0020 (9)
N6	0.0536 (15)	0.0437 (13)	0.0428 (14)	−0.0072 (12)	−0.0069 (11)	−0.0048 (11)
O1	0.0419 (13)	0.0848 (17)	0.0644 (15)	−0.0225 (12)	0.0067 (11)	0.0081 (12)
O2	0.0770 (16)	0.0419 (11)	0.0411 (11)	−0.0071 (10)	−0.0120 (10)	0.0114 (9)
O3	0.0736 (17)	0.0874 (18)	0.0875 (19)	−0.0298 (14)	−0.0399 (15)	0.0500 (16)
O4	0.0349 (11)	0.0496 (11)	0.0471 (12)	−0.0065 (9)	−0.0091 (9)	0.0052 (9)
O5	0.0426 (13)	0.0577 (14)	0.0871 (18)	−0.0013 (11)	0.0073 (12)	0.0011 (12)
O6	0.0559 (15)	0.0467 (14)	0.140 (3)	0.0042 (11)	−0.0048 (16)	0.0078 (15)

Geometric parameters (Å, º) top

C1—C2	1.479 (6)	C10—H10A	0.9600
C1—H1A	0.9600	C10—H10B	0.9600
C1—H1B	0.9600	C10—H10C	0.9600
C1—H1C	0.9600	C11—N5	1.448 (3)
C2—N1	1.469 (4)	C11—N4	1.449 (3)
C2—H2A	0.9700	C11—C12	1.544 (4)
C2—H2B	0.9700	C12—O5	1.192 (3)
C3—N1	1.446 (4)	C12—O6	1.302 (4)
C3—N2	1.475 (4)	C13—C14	1.438 (7)
C3—H3A	0.9700	C13—O6	1.485 (5)
C3—H3B	0.9700	C13—H13A	0.9700
C4—N1	1.448 (4)	C13—H13B	0.9700
C4—N3	1.468 (4)	C14—H14A	0.9600
C4—H4A	0.9700	C14—H14B	0.9600
C4—H4B	0.9700	C14—H14C	0.9600
C5—O1	1.212 (3)	C15—N6	1.452 (4)
C5—N2	1.377 (4)	C15—N4	1.474 (4)
C5—N4	1.386 (4)	C15—H15A	0.9700
C6—O2	1.210 (3)	C15—H15B	0.9700
C6—N5	1.377 (3)	C16—N6	1.448 (4)
C6—N3	1.388 (3)	C16—N5	1.469 (3)
C7—N2	1.442 (3)	C16—H16A	0.9700
C7—N3	1.444 (3)	C16—H16B	0.9700
C7—C8	1.547 (4)	C17—N6	1.471 (4)
C7—C11	1.564 (4)	C17—C18	1.506 (5)
C8—O3	1.192 (3)	C17—H17A	0.9700
C8—O4	1.293 (3)	C17—H17B	0.9700
C9—O4	1.460 (3)	C18—H18A	0.9600
C9—C10	1.464 (5)	C18—H18B	0.9600
C9—H9A	0.9700	C18—H18C	0.9600
C9—H9B	0.9700

C2—C1—H1A	109.5	O5—C12—C11	120.7 (3)
C2—C1—H1B	109.5	O6—C12—C11	112.4 (3)
H1A—C1—H1B	109.5	C14—C13—O6	108.3 (5)
C2—C1—H1C	109.5	C14—C13—H13A	110.0
H1A—C1—H1C	109.5	O6—C13—H13A	110.0
H1B—C1—H1C	109.5	C14—C13—H13B	110.0
N1—C2—C1	113.3 (3)	O6—C13—H13B	110.0
N1—C2—H2A	108.9	H13A—C13—H13B	108.4
C1—C2—H2A	108.9	C13—C14—H14A	109.5
N1—C2—H2B	108.9	C13—C14—H14B	109.5
C1—C2—H2B	108.9	H14A—C14—H14B	109.5
H2A—C2—H2B	107.7	C13—C14—H14C	109.5
N1—C3—N2	113.8 (2)	H14A—C14—H14C	109.5
N1—C3—H3A	108.8	H14B—C14—H14C	109.5
N2—C3—H3A	108.8	N6—C15—N4	113.7 (2)
N1—C3—H3B	108.8	N6—C15—H15A	108.8
N2—C3—H3B	108.8	N4—C15—H15A	108.8
H3A—C3—H3B	107.7	N6—C15—H15B	108.8
N1—C4—N3	113.4 (2)	N4—C15—H15B	108.8
N1—C4—H4A	108.9	H15A—C15—H15B	107.7
N3—C4—H4A	108.9	N6—C16—N5	113.3 (2)
N1—C4—H4B	108.9	N6—C16—H16A	108.9
N3—C4—H4B	108.9	N5—C16—H16A	108.9
H4A—C4—H4B	107.7	N6—C16—H16B	108.9
O1—C5—N2	125.9 (3)	N5—C16—H16B	108.9
O1—C5—N4	125.8 (3)	H16A—C16—H16B	107.7
N2—C5—N4	108.2 (2)	N6—C17—C18	111.9 (3)
O2—C6—N5	125.9 (3)	N6—C17—H17A	109.2
O2—C6—N3	125.9 (3)	C18—C17—H17A	109.2
N5—C6—N3	108.1 (2)	N6—C17—H17B	109.2
N2—C7—N3	111.5 (2)	C18—C17—H17B	109.2
N2—C7—C8	110.0 (2)	H17A—C17—H17B	107.9
N3—C7—C8	114.1 (2)	C17—C18—H18A	109.5
N2—C7—C11	103.2 (2)	C17—C18—H18B	109.5
N3—C7—C11	103.9 (2)	H18A—C18—H18B	109.5
C8—C7—C11	113.6 (2)	C17—C18—H18C	109.5
O3—C8—O4	126.2 (3)	H18A—C18—H18C	109.5
O3—C8—C7	120.0 (3)	H18B—C18—H18C	109.5
O4—C8—C7	113.7 (2)	C3—N1—C4	110.5 (2)
O4—C9—C10	108.1 (3)	C3—N1—C2	115.3 (3)
O4—C9—H9A	110.1	C4—N1—C2	113.4 (3)
C10—C9—H9A	110.1	C5—N2—C7	111.8 (2)
O4—C9—H9B	110.1	C5—N2—C3	124.1 (2)
C10—C9—H9B	110.1	C7—N2—C3	114.9 (2)
H9A—C9—H9B	108.4	C6—N3—C7	110.9 (2)
C9—C10—H10A	109.5	C6—N3—C4	123.2 (2)
C9—C10—H10B	109.5	C7—N3—C4	115.5 (2)
H10A—C10—H10B	109.5	C5—N4—C11	110.7 (2)
C9—C10—H10C	109.5	C5—N4—C15	121.9 (2)
H10A—C10—H10C	109.5	C11—N4—C15	115.6 (2)
H10B—C10—H10C	109.5	C6—N5—C11	111.7 (2)
N5—C11—N4	111.7 (2)	C6—N5—C16	123.5 (2)
N5—C11—C12	109.6 (2)	C11—N5—C16	115.2 (2)
N4—C11—C12	114.4 (2)	C16—N6—C15	110.0 (2)
N5—C11—C7	103.1 (2)	C16—N6—C17	114.5 (2)
N4—C11—C7	103.7 (2)	C15—N6—C17	114.0 (3)
C12—C11—C7	113.6 (2)	C8—O4—C9	116.6 (2)
O5—C12—O6	126.8 (3)	C12—O6—C13	116.6 (3)

N2—C7—C8—O3	−44.8 (4)	C8—C7—N3—C6	−134.4 (2)
N3—C7—C8—O3	−170.9 (3)	C11—C7—N3—C6	−10.2 (3)
C11—C7—C8—O3	70.3 (4)	N2—C7—N3—C4	−46.0 (3)
N2—C7—C8—O4	138.7 (2)	C8—C7—N3—C4	79.3 (3)
N3—C7—C8—O4	12.6 (3)	C11—C7—N3—C4	−156.5 (2)
C11—C7—C8—O4	−106.1 (3)	N1—C4—N3—C6	−91.5 (3)
N2—C7—C11—N5	−115.2 (2)	N1—C4—N3—C7	50.3 (3)
N3—C7—C11—N5	1.2 (2)	O1—C5—N4—C11	−166.8 (3)
C8—C7—C11—N5	125.7 (2)	N2—C5—N4—C11	15.9 (3)
N2—C7—C11—N4	1.4 (2)	O1—C5—N4—C15	−25.8 (4)
N3—C7—C11—N4	117.8 (2)	N2—C5—N4—C15	156.9 (2)
C8—C7—C11—N4	−117.7 (2)	N5—C11—N4—C5	100.0 (3)
N2—C7—C11—C12	126.2 (2)	C12—C11—N4—C5	−134.7 (2)
N3—C7—C11—C12	−117.4 (2)	C7—C11—N4—C5	−10.4 (3)
C8—C7—C11—C12	7.1 (3)	N5—C11—N4—C15	−43.7 (3)
N5—C11—C12—O5	−50.3 (4)	C12—C11—N4—C15	81.6 (3)
N4—C11—C12—O5	−176.7 (3)	C7—C11—N4—C15	−154.1 (2)
C7—C11—C12—O5	64.4 (4)	N6—C15—N4—C5	−90.4 (3)
N5—C11—C12—O6	132.3 (3)	N6—C15—N4—C11	49.0 (3)
N4—C11—C12—O6	6.0 (4)	O2—C6—N5—C11	168.3 (3)
C7—C11—C12—O6	−112.9 (3)	N3—C6—N5—C11	−15.0 (3)
N2—C3—N1—C4	51.4 (3)	O2—C6—N5—C16	24.0 (4)
N2—C3—N1—C2	−78.8 (3)	N3—C6—N5—C16	−159.4 (2)
N3—C4—N1—C3	−51.2 (3)	N4—C11—N5—C6	−102.5 (3)
N3—C4—N1—C2	79.9 (3)	C12—C11—N5—C6	129.5 (2)
C1—C2—N1—C3	−65.4 (5)	C7—C11—N5—C6	8.2 (3)
C1—C2—N1—C4	165.8 (4)	N4—C11—N5—C16	44.9 (3)
O1—C5—N2—C7	167.7 (3)	C12—C11—N5—C16	−83.0 (3)
N4—C5—N2—C7	−15.1 (3)	C7—C11—N5—C16	155.7 (2)
O1—C5—N2—C3	22.6 (4)	N6—C16—N5—C6	91.7 (3)
N4—C5—N2—C3	−160.1 (2)	N6—C16—N5—C11	−51.5 (3)
N3—C7—N2—C5	−102.8 (3)	N5—C16—N6—C15	53.3 (3)
C8—C7—N2—C5	129.7 (2)	N5—C16—N6—C17	−76.6 (3)
C11—C7—N2—C5	8.1 (3)	N4—C15—N6—C16	−52.1 (3)
N3—C7—N2—C3	45.7 (3)	N4—C15—N6—C17	78.1 (3)
C8—C7—N2—C3	−81.9 (3)	C18—C17—N6—C16	−66.0 (3)
C11—C7—N2—C3	156.6 (2)	C18—C17—N6—C15	166.1 (3)
N1—C3—N2—C5	93.8 (3)	O3—C8—O4—C9	2.6 (5)
N1—C3—N2—C7	−50.3 (3)	C7—C8—O4—C9	178.8 (2)
O2—C6—N3—C7	−167.5 (3)	C10—C9—O4—C8	−162.9 (3)
N5—C6—N3—C7	15.8 (3)	O5—C12—O6—C13	−1.5 (6)
O2—C6—N3—C4	−24.3 (4)	C11—C12—O6—C13	175.7 (3)
N5—C6—N3—C4	159.1 (2)	C14—C13—O6—C12	83.9 (5)
N2—C7—N3—C6	100.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O3ⁱ	0.97	2.53	3.460 (4)	160

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₈N₆O₆
M_r	424.47
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	292
a, b, c (Å)	20.3689 (13), 7.8804 (5), 25.9921 (16)
β (°)	91.697 (1)
V (Å³)	4170.3 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13315, 3662, 2901
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.190, 1.04
No. of reflections	3662
No. of parameters	275
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.50

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