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

She, N.-F.; Xi, H.-L.

doi:10.1107/S1600536807033739

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

N.-F. She and H.-L. Xi

The title compound, C₁₄H₁₈N₄O₈, is a glycoluril derivative, composed of two five-membered rings in envelope conformations and two six-membered rings in chair conformations. In the crystal structure, intermolecular C—H

O hydrogen bonds link the molecules into a three-dimensional network. One methyl group and the H atoms on the adjacent C atom are disordered over two positions; the site-occupancy factors are ca 0.62 and 0.38.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033739/hk2272sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033739/hk2272Isup2.hkl Contains datablock I

CCDC reference: 657763

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.042
wR factor = 0.105
Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT301_ALERT_3_C Main Residue  Disorder .........................       4.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

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           27.00
           From the CIF: _reflns_number_total               1983
           Count of symmetry unique reflns         1996
           Completeness (_total/calc)             99.35%
           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
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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

The glycoluril skeleton has served as an important building block for the preparation of a wide variety of supramolecular assemblies (Wu et al., 2002; Hof et al., 2002). The title compound is a glycoluril derivative, and is an important intermediate for the preparation of molecular clips (van Nunen et al., 1997). The molecular clip is a molecule with a rigid U-shaped cavity in which small aromatic guest molecules can be complexed by hydrogen bonding and aromatic stacking interactions (Rowan et al., 1999). We report herein the crystal structure of the title glycoluril derivative, (I).

In the molecule of (I), (Fig. 1) the bond lengths and angles are generally within normal ranges (Allen et al., 1987) and are in accordance with the corresponding values in similar compounds (Li et al., 2007; Cao et al., 2006). The rings A (O1/N1/N2/C1/C2/C5) and B (O4/N3/N4/C9/C13/C14) are not planar having total puckering amplitudes, Q_T of 1.844 (3) Å and 2.367 (3) Å, respectively, and chair conformations [φ = -28.16 (2)°, θ = 58.42 (4)° and φ = -90.10 (3)°, θ = 91.04 (3)°] (Cremer & Pople, 1975). Rings C (N1/N3/C3/C5/C9) and D (N2/N4/C4/C5/C9) have pseudo twofold axis passing through atom C9 and the mid-point of C3—N1 bond (for ring C) and atom C5 and the mid-point of C4—N4 bond (for ring D), as can be deduced from the torsion angles (Table 1). The conformations of rings C and D are envelopes, with atoms C3 and C4 at the flap positions, 0.241 (4) Å and 0.231 (3) Å from the mean planes through the other four atoms, respectively.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) link the molecules into a three dimensional network (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For related literature, see: Wu et al. (2002); Hof et al. (2002); van Nunen & Nolte (1997); Rowan et al. (1999); Burnett et al. (2003); Cremer & Pople (1975). For bond-length data, see: Allen et al. (1987). For related structures, see: Li et al. (2007); Cao et al. (2006).

Experimental top

The title compound was synthesized according to the reported procedure (Burnett et al., 2003). Crystals appropriate for X-ray data collection were obtained by slow evaporation of the dichloromethane solution at 283 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: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₄H₁₈N₄O₈	F(000) = 388
M_r = 370.32	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1973 reflections
a = 8.3182 (11) Å	θ = 2.4–24.9°
b = 12.4523 (17) Å	µ = 0.12 mm⁻¹
c = 9.0479 (12) Å	T = 292 K
β = 111.429 (2)°	Block, colourless
V = 872.4 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker SMART 4 K CCD area-detector diffractometer	1764 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 27.0°, θ_min = 2.4°
φ and ω scans	h = −10→9
5178 measured reflections	k = −15→15
1983 independent reflections	l = −8→11

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0548P)² + 0.0447P] where P = (F_o² + 2F_c²)/3
1983 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₈N₄O₈	V = 872.4 (2) Å³
M_r = 370.32	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.3182 (11) Å	µ = 0.12 mm⁻¹
b = 12.4523 (17) Å	T = 292 K
c = 9.0479 (12) Å	0.30 × 0.20 × 0.20 mm
β = 111.429 (2)°

Data collection top

Bruker SMART 4 K CCD area-detector diffractometer	1764 reflections with I > 2σ(I)
5178 measured reflections	R_int = 0.024
1983 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.11	Δρ_max = 0.15 e Å⁻³
1983 reflections	Δρ_min = −0.18 e Å⁻³
242 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	Occ. (<1)
O1	1.0609 (3)	0.93348 (19)	0.0366 (3)	0.0581 (6)
O2	0.7355 (3)	1.1226 (2)	−0.1321 (3)	0.0696 (7)
O3	0.7473 (3)	0.72136 (17)	0.0037 (3)	0.0610 (6)
O4	0.4210 (3)	0.9097 (2)	−0.1716 (3)	0.0572 (6)
O5	1.0440 (4)	1.0452 (3)	0.4466 (3)	0.0810 (8)
O6	0.8671 (3)	0.9150 (2)	0.4617 (3)	0.0637 (6)
O7	0.6082 (3)	1.08850 (19)	0.3175 (3)	0.0602 (6)
O8	0.4464 (3)	0.9393 (2)	0.2830 (3)	0.0627 (7)
N1	0.8814 (3)	1.04901 (19)	0.1154 (3)	0.0444 (6)
N2	0.8885 (3)	0.86029 (18)	0.1682 (3)	0.0422 (5)
N3	0.5932 (3)	1.0376 (2)	0.0105 (3)	0.0430 (5)
N4	0.6002 (3)	0.85184 (18)	0.0845 (3)	0.0417 (5)
C1	1.0532 (4)	0.8542 (3)	0.1461 (4)	0.0549 (8)
H1A	1.1469	0.8651	0.2471	0.066*
H1B	1.0666	0.7836	0.1069	0.066*
C2	1.0460 (4)	1.0368 (3)	0.0943 (4)	0.0561 (8)
H2A	1.0551	1.0905	0.0201	0.067*
H2B	1.1399	1.0483	0.1951	0.067*
C3	0.7366 (4)	1.0736 (2)	−0.0172 (4)	0.0465 (7)
C4	0.7467 (3)	0.8029 (2)	0.0757 (4)	0.0427 (6)
C5	0.8418 (3)	0.9662 (2)	0.2081 (3)	0.0384 (6)
C6	0.9305 (4)	0.9837 (3)	0.3875 (4)	0.0495 (7)
C7	0.9423 (6)	0.9107 (4)	0.6352 (4)	0.0835 (12)
H7A	1.0499	0.9505	0.6737	0.100*	0.379 (16)
H7B	0.8637	0.9424	0.6799	0.100*	0.379 (16)
H7C	0.9169	0.9763	0.6799	0.100*	0.621 (16)
H7D	1.0655	0.9008	0.6717	0.100*	0.621 (16)
C8'	0.973 (4)	0.8013 (13)	0.681 (2)	0.120 (5)	0.379 (16)
H8D	0.8643	0.7644	0.6539	0.179*	0.379 (16)
H8E	1.0342	0.7970	0.7939	0.179*	0.379 (16)
H8F	1.0400	0.7684	0.6272	0.179*	0.379 (16)
C8	0.864 (2)	0.8187 (11)	0.6818 (12)	0.120 (5)	0.621 (16)
H8B	0.7419	0.8306	0.6512	0.179*	0.621 (16)
H8A	0.9146	0.8095	0.7949	0.179*	0.621 (16)
H8C	0.8831	0.7553	0.6302	0.179*	0.621 (16)
C9	0.6399 (3)	0.9613 (2)	0.1413 (3)	0.0371 (6)
C10	0.5515 (3)	0.9931 (2)	0.2571 (3)	0.0437 (6)
C11	0.5389 (6)	1.1295 (4)	0.4340 (5)	0.0843 (13)
H11A	0.4160	1.1428	0.3836	0.101*
H11B	0.5569	1.0774	0.5184	0.101*
C12	0.6285 (8)	1.2279 (4)	0.4977 (6)	0.1070 (18)
H12A	0.7496	1.2135	0.5494	0.161*
H12B	0.5841	1.2575	0.5730	0.161*
H12C	0.6116	1.2783	0.4130	0.161*
C13	0.4298 (4)	1.0173 (3)	−0.1184 (4)	0.0540 (8)
H13A	0.3354	1.0311	−0.0823	0.065*
H13B	0.4179	1.0657	−0.2058	0.065*
C14	0.4365 (4)	0.8373 (3)	−0.0448 (4)	0.0513 (7)
H14A	0.4276	0.7640	−0.0832	0.062*
H14B	0.3430	0.8497	−0.0071	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0501 (11)	0.0574 (15)	0.0793 (15)	0.0006 (10)	0.0384 (11)	0.0035 (12)
O2	0.0736 (15)	0.0679 (17)	0.0735 (16)	0.0006 (12)	0.0340 (13)	0.0305 (14)
O3	0.0601 (13)	0.0372 (12)	0.0925 (16)	0.0007 (10)	0.0360 (12)	−0.0151 (12)
O4	0.0512 (11)	0.0601 (14)	0.0532 (12)	−0.0013 (11)	0.0106 (9)	−0.0125 (11)
O5	0.0752 (17)	0.089 (2)	0.0687 (16)	−0.0352 (16)	0.0146 (13)	−0.0135 (15)
O6	0.0672 (13)	0.0738 (16)	0.0426 (11)	−0.0190 (12)	0.0113 (10)	0.0056 (11)
O7	0.0700 (14)	0.0540 (13)	0.0698 (14)	−0.0068 (11)	0.0413 (11)	−0.0195 (12)
O8	0.0542 (12)	0.0740 (17)	0.0763 (15)	−0.0143 (11)	0.0431 (11)	−0.0126 (13)
N1	0.0419 (12)	0.0373 (13)	0.0579 (14)	−0.0052 (10)	0.0230 (11)	0.0045 (11)
N2	0.0368 (11)	0.0353 (12)	0.0565 (14)	0.0021 (9)	0.0195 (10)	0.0033 (11)
N3	0.0409 (12)	0.0391 (12)	0.0492 (13)	0.0033 (10)	0.0166 (10)	0.0024 (11)
N4	0.0365 (11)	0.0354 (12)	0.0566 (14)	−0.0031 (9)	0.0209 (10)	−0.0043 (11)
C1	0.0400 (15)	0.0481 (18)	0.080 (2)	0.0081 (13)	0.0256 (14)	0.0042 (17)
C2	0.0431 (16)	0.0531 (18)	0.081 (2)	−0.0059 (14)	0.0326 (15)	0.0050 (18)
C3	0.0519 (16)	0.0347 (14)	0.0573 (17)	0.0012 (12)	0.0251 (13)	0.0034 (13)
C4	0.0446 (15)	0.0310 (14)	0.0572 (17)	0.0017 (11)	0.0241 (13)	0.0035 (13)
C5	0.0369 (12)	0.0335 (13)	0.0476 (15)	−0.0021 (10)	0.0188 (11)	−0.0002 (11)
C6	0.0389 (14)	0.0524 (18)	0.0527 (17)	−0.0025 (13)	0.0113 (12)	−0.0023 (14)
C7	0.098 (3)	0.096 (3)	0.046 (2)	−0.007 (3)	0.0133 (19)	0.004 (2)
C8'	0.172 (13)	0.127 (7)	0.055 (3)	−0.058 (9)	0.037 (7)	0.011 (4)
C8	0.172 (13)	0.127 (7)	0.055 (3)	−0.058 (9)	0.037 (7)	0.011 (4)
C9	0.0358 (12)	0.0320 (13)	0.0447 (15)	−0.0019 (10)	0.0159 (11)	−0.0020 (11)
C10	0.0383 (13)	0.0459 (16)	0.0485 (15)	−0.0005 (11)	0.0177 (11)	−0.0038 (13)
C11	0.095 (3)	0.084 (3)	0.091 (3)	−0.003 (2)	0.055 (3)	−0.036 (2)
C12	0.172 (5)	0.074 (3)	0.084 (3)	0.002 (3)	0.057 (3)	−0.025 (3)
C13	0.0450 (16)	0.0562 (19)	0.0551 (17)	0.0096 (13)	0.0113 (13)	0.0024 (15)
C14	0.0438 (15)	0.0459 (17)	0.064 (2)	−0.0068 (13)	0.0195 (13)	−0.0103 (14)

Geometric parameters (Å, º) top

C1—O1	1.416 (4)	C8'—H8D	0.9600
C1—N2	1.458 (4)	C8'—H8E	0.9600
C1—H1A	0.9700	C8'—H8F	0.9600
C1—H1B	0.9700	C8—H8B	0.9600
C2—O1	1.411 (4)	C8—H8A	0.9600
C2—N1	1.458 (4)	C8—H8C	0.9600
C2—H2A	0.9700	C9—N4	1.451 (4)
C2—H2B	0.9700	C9—N3	1.455 (4)
C3—O2	1.203 (4)	C9—C10	1.536 (4)
C3—N3	1.380 (4)	C10—O8	1.191 (3)
C3—N1	1.389 (4)	C10—O7	1.320 (4)
C4—O3	1.208 (4)	C11—C12	1.441 (7)
C4—N2	1.371 (4)	C11—O7	1.466 (4)
C4—N4	1.390 (3)	C11—H11A	0.9700
C5—N1	1.442 (4)	C11—H11B	0.9700
C5—N2	1.457 (3)	C12—H12A	0.9600
C5—C6	1.533 (4)	C12—H12B	0.9600
C5—C9	1.565 (3)	C12—H12C	0.9600
C6—O5	1.181 (4)	C13—O4	1.417 (4)
C6—O6	1.311 (4)	C13—N3	1.454 (4)
C7—C8'	1.420 (16)	C13—H13A	0.9700
C7—C8	1.455 (10)	C13—H13B	0.9700
C7—O6	1.463 (4)	C14—O4	1.427 (4)
C7—H7A	0.9700	C14—N4	1.447 (4)
C7—H7B	0.9700	C14—H14A	0.9700
C7—H7C	0.9692	C14—H14B	0.9700
C7—H7D	0.9628

C2—O1—C1	110.1 (2)	C8—C7—H7C	110.7
C13—O4—C14	110.3 (2)	O6—C7—H7C	110.1
C6—O6—C7	118.6 (3)	H7A—C7—H7C	74.4
C10—O7—C11	115.8 (3)	C8'—C7—H7D	74.0
C3—N1—C5	110.5 (2)	C8—C7—H7D	109.5
C3—N1—C2	118.0 (3)	O6—C7—H7D	110.9
C5—N1—C2	115.3 (2)	H7B—C7—H7D	134.8
C4—N2—C5	112.0 (2)	H7C—C7—H7D	109.4
C4—N2—C1	122.1 (3)	C7—C8'—H8D	109.5
C5—N2—C1	115.5 (2)	H7D—C8'—H8D	147.9
C3—N3—C13	121.8 (3)	C7—C8'—H8E	109.5
C3—N3—C9	111.6 (2)	H7D—C8'—H8E	91.2
C13—N3—C9	115.6 (2)	C7—C8'—H8F	109.4
C4—N4—C14	119.0 (2)	H7D—C8'—H8F	84.9
C4—N4—C9	109.9 (2)	C7—C8—H8B	109.5
C14—N4—C9	115.4 (2)	C7—C8—H8A	109.5
O1—C1—N2	110.2 (2)	H8B—C8—H8A	109.5
O1—C1—H1A	109.6	C7—C8—H8C	109.4
N2—C1—H1A	109.6	H8B—C8—H8C	109.5
O1—C1—H1B	109.6	H8A—C8—H8C	109.5
N2—C1—H1B	109.6	N4—C9—N3	111.5 (2)
H1A—C1—H1B	108.1	N4—C9—C10	112.4 (2)
O1—C2—N1	110.9 (2)	N3—C9—C10	109.5 (2)
O1—C2—H2A	109.5	N4—C9—C5	104.3 (2)
N1—C2—H2A	109.5	N3—C9—C5	102.6 (2)
O1—C2—H2B	109.5	C10—C9—C5	116.1 (2)
N1—C2—H2B	109.5	O8—C10—O7	127.0 (3)
H2A—C2—H2B	108.0	O8—C10—C9	123.9 (3)
O2—C3—N3	126.0 (3)	O7—C10—C9	109.1 (2)
O2—C3—N1	126.1 (3)	C12—C11—O7	107.5 (4)
N3—C3—N1	107.8 (3)	C12—C11—H11A	110.2
O3—C4—N2	126.5 (3)	O7—C11—H11A	110.2
O3—C4—N4	125.2 (3)	C12—C11—H11B	110.2
N2—C4—N4	108.3 (2)	O7—C11—H11B	110.2
N1—C5—N2	111.4 (2)	H11A—C11—H11B	108.5
N1—C5—C6	113.0 (2)	C11—C12—H12A	109.5
N2—C5—C6	108.8 (2)	C11—C12—H12B	109.5
N1—C5—C9	104.1 (2)	H12A—C12—H12B	109.5
N2—C5—C9	102.4 (2)	C11—C12—H12C	109.5
C6—C5—C9	116.6 (2)	H12A—C12—H12C	109.5
O5—C6—O6	126.5 (3)	H12B—C12—H12C	109.5
O5—C6—C5	124.6 (3)	O4—C13—N3	110.7 (2)
O6—C6—C5	108.8 (2)	O4—C13—H13A	109.5
C8'—C7—O6	108.1 (9)	N3—C13—H13A	109.5
C8—C7—O6	106.2 (5)	O4—C13—H13B	109.5
C8'—C7—H7A	110.1	N3—C13—H13B	109.5
C8—C7—H7A	138.7	H13A—C13—H13B	108.1
O6—C7—H7A	110.1	O4—C14—N4	110.7 (2)
C8'—C7—H7B	110.0	O4—C14—H14A	109.5
C8—C7—H7B	75.9	N4—C14—H14A	109.5
O6—C7—H7B	110.1	O4—C14—H14B	109.5
H7A—C7—H7B	108.4	N4—C14—H14B	109.5
C8'—C7—H7C	136.8	H14A—C14—H14B	108.1

N2—C1—O1—C2	60.7 (3)	N1—C5—C9—N4	120.5 (2)
O1—C1—N2—C4	90.1 (3)	N2—C5—C9—N4	4.3 (3)
O1—C1—N2—C5	−52.1 (4)	C6—C5—C9—N4	−114.3 (3)
N1—C2—O1—C1	−60.9 (3)	N1—C5—C9—N3	4.1 (3)
O1—C2—N1—C3	−81.6 (3)	N2—C5—C9—N3	−112.1 (2)
O1—C2—N1—C5	52.0 (4)	C6—C5—C9—N3	129.3 (2)
O2—C3—N1—C5	−164.3 (3)	N1—C5—C9—C10	−115.4 (3)
N3—C3—N1—C5	19.3 (3)	N2—C5—C9—C10	128.5 (2)
O2—C3—N1—C2	−28.6 (5)	C6—C5—C9—C10	9.9 (3)
N3—C3—N1—C2	155.0 (3)	O5—C6—O6—C7	−0.7 (6)
O2—C3—N3—C13	24.5 (5)	C5—C6—O6—C7	175.2 (3)
N1—C3—N3—C13	−159.0 (3)	C8'—C7—O6—C6	−132.7 (13)
O2—C3—N3—C9	167.1 (3)	C8—C7—O6—C6	−172.3 (9)
N1—C3—N3—C9	−16.5 (3)	N4—C9—N3—C3	−103.8 (3)
O3—C4—N2—C5	167.0 (3)	C10—C9—N3—C3	131.2 (2)
N4—C4—N2—C5	−15.9 (3)	C5—C9—N3—C3	7.3 (3)
O3—C4—N2—C1	23.7 (5)	N4—C9—N3—C13	41.3 (3)
N4—C4—N2—C1	−159.2 (3)	C10—C9—N3—C13	−83.8 (3)
O3—C4—N4—C14	−27.8 (4)	C5—C9—N3—C13	152.4 (2)
N2—C4—N4—C14	155.0 (2)	N3—C9—N4—C4	96.1 (2)
O3—C4—N4—C9	−164.1 (3)	C10—C9—N4—C4	−140.5 (2)
N2—C4—N4—C9	18.7 (3)	C5—C9—N4—C4	−13.9 (3)
N2—C5—N1—C3	95.5 (3)	N3—C9—N4—C14	−41.8 (3)
C6—C5—N1—C3	−141.7 (2)	C10—C9—N4—C14	81.6 (3)
C9—C5—N1—C3	−14.2 (3)	C5—C9—N4—C14	−151.9 (2)
N2—C5—N1—C2	−41.5 (3)	N4—C9—C10—O8	−8.5 (4)
C6—C5—N1—C2	81.3 (3)	N3—C9—C10—O8	116.1 (3)
C9—C5—N1—C2	−151.1 (2)	C5—C9—C10—O8	−128.3 (3)
N1—C5—N2—C4	−104.0 (3)	N4—C9—C10—O7	173.0 (2)
C6—C5—N2—C4	130.8 (2)	N3—C9—C10—O7	−62.5 (3)
C9—C5—N2—C4	6.7 (3)	C5—C9—C10—O7	53.1 (3)
N1—C5—N2—C1	41.9 (3)	O8—C10—O7—C11	2.9 (5)
C6—C5—N2—C1	−83.3 (3)	C9—C10—O7—C11	−178.6 (3)
C9—C5—N2—C1	152.6 (2)	C12—C11—O7—C10	174.1 (4)
N1—C5—C6—O5	−13.6 (4)	N3—C13—O4—C14	59.8 (3)
N2—C5—C6—O5	110.6 (4)	O4—C13—N3—C3	90.0 (4)
C9—C5—C6—O5	−134.3 (4)	O4—C13—N3—C9	−51.1 (3)
N1—C5—C6—O6	170.4 (2)	O4—C14—N4—C4	−81.8 (3)
N2—C5—C6—O6	−65.4 (3)	O4—C14—N4—C9	52.2 (3)
C9—C5—C6—O6	49.7 (3)	N4—C14—O4—C13	−60.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O8ⁱ	0.97	2.56	3.223 (4)	125
C1—H1B···O2ⁱⁱ	0.97	2.55	3.404 (4)	147
C2—H2A···O3ⁱⁱⁱ	0.97	2.38	3.183 (4)	140
C8—H8A···O1^iv	0.96	2.59	3.345 (12)	136

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₈N₄O₈
M_r	370.32
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	292
a, b, c (Å)	8.3182 (11), 12.4523 (17), 9.0479 (12)
β (°)	111.429 (2)
V (Å³)	872.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4 K CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5178, 1983, 1764
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.105, 1.11
No. of reflections	1983
No. of parameters	242
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.18

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

Selected torsion angles (º) top

N3—C3—N1—C5	19.3 (3)	C9—C5—N2—C4	6.7 (3)
N1—C3—N3—C9	−16.5 (3)	N2—C5—C9—N4	4.3 (3)
N4—C4—N2—C5	−15.9 (3)	N1—C5—C9—N3	4.1 (3)
N2—C4—N4—C9	18.7 (3)	C5—C9—N3—C3	7.3 (3)
C9—C5—N1—C3	−14.2 (3)	C5—C9—N4—C4	−13.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O8ⁱ	0.97	2.56	3.223 (4)	125.4
C1—H1B···O2ⁱⁱ	0.97	2.55	3.404 (4)	146.8
C2—H2A···O3ⁱⁱⁱ	0.97	2.38	3.183 (4)	140.0
C8—H8A···O1^iv	0.96	2.59	3.345 (12)	135.8

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

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