Diethyl 5,10-dihydro-9-meth­oxy-6-nitro-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a,10a,11a-tetra­azabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxyl­ate

Zhou, B.-H.; Qu, J.-L.; Wu, A.-X.

doi:10.1107/S1600536805028977

Diethyl 5,10-dihydro-9-methoxy-6-nitro-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa-3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate

The crystal structure of the title compound, C₂₁H₂₃N₅O₁₀, an important intermediate for molecular tweezers, shows intermolecular hydrogen bonding.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805028977/ww6404sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805028977/ww6404Isup2.hkl Contains datablock I

CCDC reference: 273829

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.003 Å
R factor = 0.045
wR factor = 0.135
Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.77 Ratio

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

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

Comment top

Derivatives of glycoluril have been employed in many applications, including polymer cross-linking, explosives, slow-release fertilizers, crosslinkers, assessment of drug reactivity (Jeon et al., 2005), stabilization of organic compounds against photo-degradation and combinatorial chemistry (Wu, Fettinger & Isaacs, 2002; Wu, Chakraborty et al., 2002). The use of glycoluril derivatives as building blocks for self-assembly, molecular recognition (Kang & Kim, 2005) and catalysis in chloroform has been reported (Conn & Rebek, 1997). Many methylene-bridged glycoluril dimers have been synthesized from soluble organic diethoxycarbonyl glycoluril derivatives (Witt et al., 2000). In this paper, we present the X-ray crystal structure of the title compound (I).

The X-ray crystallographic structure of (I) is shown in Fig. 1. Selected bond distances and torsion angles describing the molecular conformation are listed in Table 1. The molecules are connected by intermolecular hydrogen bonding (Fig 2). In the crystal structure, the angle between the two five-membered rings of the glycoluril is 110°.

Experimental top

The title compound was synthesized according to the literature procedure of Wu, Chakraborty et al. (2002), using paraformaldehyde (0.18 g, 6 mmol), 2,3-bisbromomethyl-1-methoxy-4-nitrobenzene (4 mmol, 1.36 g) and glycoluril (5.72 g, 20 mmol) as starting materials. Crystals suitable for data collection were obtained by slow evaporation from methanol–1,2-dichloroethane (Ratio?) solution at 293 K.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. A view of the molecule of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 50% probability level. H atoms are represented by circles of arbitrary size.
	Fig. 2. The intermolecular hydrogen bonding in the crystal structure of (I). Hydrogen-bonding interactions are indicated by dashed lines.

Diethyl 5,10-dihydro-9-methoxy-6-nitro-4,11-dioxo-cis-1H,3H,4H,11H-2-oxa- 3a,4a,10a,11a-tetraazabenz[f]indeno[2,1,7-ija]azulene-11b,11c-dicarboxylate top

Crystal data top

C₂₁H₂₃N₅O₁₀	Z = 2
M_r = 505.44	F(000) = 528
Triclinic, P1	D_x = 1.499 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.756 (2) Å	Cell parameters from 4159 reflections
b = 10.608 (2) Å	θ = 2.6–28.3°
c = 11.716 (3) Å	µ = 0.12 mm⁻¹
α = 110.123 (4)°	T = 292 K
β = 98.754 (4)°	Block, yellow
γ = 92.119 (4)°	0.30 × 0.20 × 0.20 mm
V = 1119.9 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 26.0°, θ_min = 1.9°
ϕ and ω scans	h = −12→12
8700 measured reflections	k = −13→13
4340 independent reflections	l = −14→14

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.073P)² + 0.1853P] where P = (F_o² + 2F_c²)/3
4340 reflections	(Δ/σ)_max < 0.001
328 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₁H₂₃N₅O₁₀	γ = 92.119 (4)°
M_r = 505.44	V = 1119.9 (4) Å³
Triclinic, P1	Z = 2
a = 9.756 (2) Å	Mo Kα radiation
b = 10.608 (2) Å	µ = 0.12 mm⁻¹
c = 11.716 (3) Å	T = 292 K
α = 110.123 (4)°	0.30 × 0.20 × 0.20 mm
β = 98.754 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 reflections with I > 2σ(I)
8700 measured reflections	R_int = 0.019
4340 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.26 e Å⁻³
4340 reflections	Δρ_min = −0.17 e Å⁻³
328 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	0.6843 (3)	−0.2774 (2)	0.4461 (2)	0.0717 (7)
H1A	0.7116	−0.2796	0.5276	0.108*
H1B	0.7015	−0.3607	0.3862	0.108*
H1C	0.5869	−0.2654	0.4326	0.108*
C2	0.7505 (2)	−0.0408 (2)	0.50995 (19)	0.0472 (5)
C3	0.6793 (2)	−0.0129 (2)	0.6080 (2)	0.0591 (6)
H3	0.6339	−0.0829	0.6228	0.071*
C4	0.6757 (2)	0.1178 (2)	0.6835 (2)	0.0594 (6)
H4	0.6249	0.1373	0.7475	0.071*
C5	0.7479 (2)	0.2202 (2)	0.66358 (17)	0.0486 (5)
C6	0.81973 (19)	0.19730 (19)	0.56482 (16)	0.0412 (4)
C7	0.81672 (18)	0.06393 (18)	0.48470 (17)	0.0404 (4)
C8	0.87676 (19)	0.03312 (19)	0.36697 (17)	0.0417 (4)
H8A	0.9741	0.0684	0.3878	0.050*
H8B	0.8722	−0.0639	0.3261	0.050*
C9	0.8897 (2)	0.30903 (19)	0.53468 (16)	0.0434 (4)
H9A	0.8947	0.3935	0.6033	0.052*
H9B	0.9841	0.2895	0.5234	0.052*
C10	0.67423 (18)	0.03475 (17)	0.21357 (16)	0.0379 (4)
C11	0.6829 (2)	0.36657 (17)	0.42607 (16)	0.0390 (4)
C12	0.82507 (18)	0.23392 (17)	0.30060 (15)	0.0354 (4)
C13	0.96537 (19)	0.26171 (19)	0.26505 (18)	0.0433 (4)
C14	1.0811 (3)	0.2167 (3)	0.0922 (3)	0.0732 (7)
H14A	1.1550	0.1670	0.1156	0.088*
H14B	1.1152	0.3114	0.1220	0.088*
C15	1.0384 (4)	0.1660 (3)	−0.0441 (3)	0.0982 (10)
H15A	0.9939	0.0758	−0.0716	0.147*
H15B	1.1191	0.1659	−0.0818	0.147*
H15C	0.9745	0.2234	−0.0671	0.147*
C16	0.69285 (18)	0.25597 (17)	0.21718 (15)	0.0358 (4)
C17	0.7186 (2)	0.31826 (19)	0.12066 (17)	0.0435 (4)
C18	0.8069 (3)	0.5209 (3)	0.1019 (3)	0.0697 (7)
H18A	0.8904	0.5827	0.1392	0.084*
H18B	0.8189	0.4627	0.0203	0.084*
C19	0.6869 (3)	0.5974 (3)	0.0909 (3)	0.0929 (9)
H19A	0.6031	0.5369	0.0612	0.139*
H19B	0.6970	0.6426	0.0339	0.139*
H19C	0.6818	0.6628	0.1703	0.139*
C20	0.46796 (19)	0.1200 (2)	0.12854 (18)	0.0470 (5)
H20A	0.4446	0.1535	0.0614	0.056*
H20B	0.4266	0.0276	0.1011	0.056*
C21	0.4703 (2)	0.3364 (2)	0.27194 (19)	0.0483 (5)
H21A	0.4307	0.3907	0.3419	0.058*
H21B	0.4469	0.3713	0.2057	0.058*
N1	0.7426 (2)	0.3560 (2)	0.75081 (16)	0.0600 (5)
N2	0.80236 (15)	0.09153 (14)	0.28193 (13)	0.0360 (3)
N3	0.81338 (16)	0.32315 (14)	0.42234 (13)	0.0387 (4)
N4	0.61829 (15)	0.12341 (14)	0.15920 (13)	0.0379 (3)
N5	0.61892 (16)	0.34618 (14)	0.30650 (13)	0.0384 (4)
O1	0.76296 (16)	−0.16808 (14)	0.43397 (14)	0.0594 (4)
O2	0.8501 (2)	0.42990 (19)	0.79215 (16)	0.0834 (6)
O3	0.6308 (2)	0.38728 (18)	0.78133 (16)	0.0791 (5)
O4	0.62129 (14)	−0.07552 (13)	0.19868 (14)	0.0545 (4)
O5	0.63453 (16)	0.41730 (14)	0.51834 (12)	0.0541 (4)
O6	1.06315 (16)	0.32901 (19)	0.33582 (15)	0.0732 (5)
O7	0.95947 (14)	0.19839 (14)	0.14557 (13)	0.0517 (4)
O8	0.67792 (18)	0.26598 (17)	0.01277 (13)	0.0667 (4)
O9	0.78743 (16)	0.43882 (14)	0.17747 (13)	0.0563 (4)
O10	0.41237 (13)	0.20003 (14)	0.23236 (13)	0.0502 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0908 (18)	0.0483 (13)	0.0754 (17)	−0.0123 (12)	0.0087 (14)	0.0254 (12)
C2	0.0523 (11)	0.0441 (11)	0.0488 (11)	0.0047 (9)	0.0033 (9)	0.0235 (9)
C3	0.0711 (14)	0.0567 (13)	0.0599 (13)	0.0001 (11)	0.0184 (11)	0.0313 (11)
C4	0.0727 (15)	0.0660 (15)	0.0487 (12)	0.0068 (11)	0.0204 (11)	0.0280 (11)
C5	0.0590 (12)	0.0511 (12)	0.0350 (10)	0.0070 (9)	0.0036 (9)	0.0163 (9)
C6	0.0429 (10)	0.0464 (11)	0.0344 (10)	0.0037 (8)	−0.0020 (7)	0.0181 (8)
C7	0.0411 (10)	0.0432 (10)	0.0399 (10)	0.0071 (8)	0.0025 (8)	0.0198 (8)
C8	0.0423 (10)	0.0404 (10)	0.0455 (11)	0.0105 (8)	0.0069 (8)	0.0189 (8)
C9	0.0503 (11)	0.0412 (10)	0.0345 (10)	−0.0008 (8)	−0.0008 (8)	0.0123 (8)
C10	0.0429 (10)	0.0326 (9)	0.0358 (9)	0.0053 (7)	0.0109 (7)	0.0072 (7)
C11	0.0548 (11)	0.0279 (9)	0.0343 (10)	0.0074 (7)	0.0090 (8)	0.0102 (7)
C12	0.0420 (10)	0.0314 (9)	0.0319 (9)	0.0026 (7)	0.0059 (7)	0.0105 (7)
C13	0.0432 (10)	0.0429 (10)	0.0452 (11)	−0.0006 (8)	0.0053 (8)	0.0190 (9)
C14	0.0599 (14)	0.0839 (17)	0.0849 (18)	0.0027 (12)	0.0400 (13)	0.0303 (15)
C15	0.125 (3)	0.094 (2)	0.083 (2)	0.0007 (18)	0.0662 (19)	0.0215 (17)
C16	0.0433 (10)	0.0332 (9)	0.0308 (9)	0.0066 (7)	0.0085 (7)	0.0102 (7)
C17	0.0487 (11)	0.0472 (11)	0.0375 (11)	0.0085 (8)	0.0090 (8)	0.0178 (9)
C18	0.0809 (16)	0.0751 (16)	0.0756 (16)	0.0021 (13)	0.0198 (13)	0.0528 (14)
C19	0.124 (3)	0.0777 (19)	0.102 (2)	0.0239 (17)	0.0306 (19)	0.0571 (18)
C20	0.0418 (10)	0.0498 (11)	0.0437 (11)	0.0072 (8)	0.0019 (8)	0.0114 (9)
C21	0.0529 (12)	0.0498 (12)	0.0437 (11)	0.0195 (9)	0.0119 (9)	0.0157 (9)
N1	0.0848 (14)	0.0602 (12)	0.0363 (9)	0.0071 (11)	0.0101 (9)	0.0188 (9)
N2	0.0403 (8)	0.0317 (8)	0.0370 (8)	0.0051 (6)	0.0069 (6)	0.0132 (6)
N3	0.0477 (9)	0.0353 (8)	0.0312 (8)	0.0038 (6)	0.0032 (6)	0.0112 (6)
N4	0.0395 (8)	0.0334 (8)	0.0361 (8)	0.0050 (6)	0.0033 (6)	0.0077 (6)
N5	0.0487 (9)	0.0360 (8)	0.0314 (8)	0.0128 (6)	0.0093 (6)	0.0113 (6)
O1	0.0788 (10)	0.0413 (8)	0.0631 (10)	0.0035 (7)	0.0155 (8)	0.0238 (7)
O2	0.1094 (15)	0.0730 (12)	0.0498 (10)	−0.0157 (11)	0.0104 (10)	0.0029 (9)
O3	0.1034 (14)	0.0799 (12)	0.0611 (11)	0.0329 (10)	0.0337 (10)	0.0235 (9)
O4	0.0571 (8)	0.0344 (7)	0.0666 (10)	−0.0032 (6)	0.0017 (7)	0.0155 (7)
O5	0.0748 (10)	0.0528 (8)	0.0346 (7)	0.0235 (7)	0.0160 (7)	0.0111 (6)
O6	0.0548 (9)	0.0950 (13)	0.0601 (10)	−0.0241 (9)	0.0021 (8)	0.0217 (9)
O7	0.0455 (7)	0.0591 (9)	0.0496 (8)	0.0008 (6)	0.0198 (6)	0.0138 (7)
O8	0.0872 (11)	0.0786 (11)	0.0331 (8)	−0.0012 (9)	0.0054 (7)	0.0215 (8)
O9	0.0775 (10)	0.0489 (8)	0.0498 (9)	−0.0012 (7)	0.0123 (7)	0.0270 (7)
O10	0.0431 (7)	0.0566 (9)	0.0509 (8)	0.0106 (6)	0.0120 (6)	0.0170 (7)

Geometric parameters (Å, º) top

C1—O1	1.426 (3)	C13—O6	1.187 (2)
C1—H1A	0.9600	C13—O7	1.319 (2)
C1—H1B	0.9600	C14—O7	1.459 (2)
C1—H1C	0.9600	C14—C15	1.484 (4)
C2—O1	1.359 (2)	C14—H14A	0.9700
C2—C3	1.383 (3)	C14—H14B	0.9700
C2—C7	1.404 (3)	C15—H15A	0.9600
C3—C4	1.369 (3)	C15—H15B	0.9600
C3—H3	0.9300	C15—H15C	0.9600
C4—C5	1.377 (3)	C16—N4	1.444 (2)
C4—H4	0.9300	C16—N5	1.457 (2)
C5—C6	1.398 (3)	C16—C17	1.538 (2)
C5—N1	1.460 (3)	C17—O8	1.188 (2)
C6—C7	1.399 (3)	C17—O9	1.321 (2)
C6—C9	1.515 (3)	C18—C19	1.463 (4)
C7—C8	1.517 (3)	C18—O9	1.465 (2)
C8—N2	1.463 (2)	C18—H18A	0.9700
C8—H8A	0.9700	C18—H18B	0.9700
C8—H8B	0.9700	C19—H19A	0.9600
C9—N3	1.468 (2)	C19—H19B	0.9600
C9—H9A	0.9700	C19—H19C	0.9600
C9—H9B	0.9700	C20—O10	1.421 (2)
C10—O4	1.205 (2)	C20—N4	1.452 (2)
C10—N2	1.369 (2)	C20—H20A	0.9700
C10—N4	1.390 (2)	C20—H20B	0.9700
C11—O5	1.206 (2)	C21—O10	1.423 (2)
C11—N3	1.372 (2)	C21—N5	1.435 (2)
C11—N5	1.384 (2)	C21—H21A	0.9700
C12—N3	1.439 (2)	C21—H21B	0.9700
C12—N2	1.453 (2)	N1—O2	1.213 (3)
C12—C13	1.537 (2)	N1—O3	1.221 (3)
C12—C16	1.571 (2)

O1—C1—H1A	109.5	C14—C15—H15B	109.5
O1—C1—H1B	109.5	H15A—C15—H15B	109.5
H1A—C1—H1B	109.5	C14—C15—H15C	109.5
O1—C1—H1C	109.5	H15A—C15—H15C	109.5
H1A—C1—H1C	109.5	H15B—C15—H15C	109.5
H1B—C1—H1C	109.5	N4—C16—N5	111.54 (14)
O1—C2—C3	123.38 (18)	N4—C16—C17	111.24 (14)
O1—C2—C7	115.93 (18)	N5—C16—C17	109.63 (14)
C3—C2—C7	120.68 (19)	N4—C16—C12	104.10 (13)
C4—C3—C2	120.0 (2)	N5—C16—C12	103.10 (13)
C4—C3—H3	120.0	C17—C16—C12	116.90 (14)
C2—C3—H3	120.0	O8—C17—O9	126.44 (18)
C3—C4—C5	119.4 (2)	O8—C17—C16	124.30 (18)
C3—C4—H4	120.3	O9—C17—C16	109.22 (15)
C5—C4—H4	120.3	C19—C18—O9	110.8 (2)
C4—C5—C6	122.67 (19)	C19—C18—H18A	109.5
C4—C5—N1	115.84 (19)	O9—C18—H18A	109.5
C6—C5—N1	121.47 (18)	C19—C18—H18B	109.5
C5—C6—C7	117.35 (17)	O9—C18—H18B	109.5
C5—C6—C9	123.66 (17)	H18A—C18—H18B	108.1
C7—C6—C9	118.80 (16)	C18—C19—H19A	109.5
C6—C7—C2	119.67 (17)	C18—C19—H19B	109.5
C6—C7—C8	120.29 (16)	H19A—C19—H19B	109.5
C2—C7—C8	119.94 (17)	C18—C19—H19C	109.5
N2—C8—C7	112.31 (14)	H19A—C19—H19C	109.5
N2—C8—H8A	109.1	H19B—C19—H19C	109.5
C7—C8—H8A	109.1	O10—C20—N4	110.87 (15)
N2—C8—H8B	109.1	O10—C20—H20A	109.5
C7—C8—H8B	109.1	N4—C20—H20A	109.5
H8A—C8—H8B	107.9	O10—C20—H20B	109.5
N3—C9—C6	111.48 (14)	N4—C20—H20B	109.5
N3—C9—H9A	109.3	H20A—C20—H20B	108.1
C6—C9—H9A	109.3	O10—C21—N5	110.72 (14)
N3—C9—H9B	109.3	O10—C21—H21A	109.5
C6—C9—H9B	109.3	N5—C21—H21A	109.5
H9A—C9—H9B	108.0	O10—C21—H21B	109.5
O4—C10—N2	125.98 (17)	N5—C21—H21B	109.5
O4—C10—N4	125.68 (17)	H21A—C21—H21B	108.1
N2—C10—N4	108.27 (14)	O2—N1—O3	123.6 (2)
O5—C11—N3	125.57 (17)	O2—N1—C5	118.3 (2)
O5—C11—N5	126.22 (17)	O3—N1—C5	118.0 (2)
N3—C11—N5	108.18 (15)	C10—N2—C12	112.36 (14)
N3—C12—N2	114.23 (14)	C10—N2—C8	120.97 (14)
N3—C12—C13	112.07 (14)	C12—N2—C8	121.83 (14)
N2—C12—C13	109.38 (14)	C11—N3—C12	111.60 (14)
N3—C12—C16	103.11 (13)	C11—N3—C9	117.68 (15)
N2—C12—C16	102.39 (13)	C12—N3—C9	122.33 (15)
C13—C12—C16	115.31 (14)	C10—N4—C16	110.76 (14)
O6—C13—O7	126.17 (18)	C10—N4—C20	119.12 (15)
O6—C13—C12	124.39 (18)	C16—N4—C20	115.74 (14)
O7—C13—C12	109.44 (15)	C11—N5—C21	122.03 (15)
O7—C14—C15	107.9 (2)	C11—N5—C16	110.98 (14)
O7—C14—H14A	110.1	C21—N5—C16	116.37 (14)
C15—C14—H14A	110.1	C2—O1—C1	118.21 (18)
O7—C14—H14B	110.1	C13—O7—C14	118.00 (17)
C15—C14—H14B	110.1	C17—O9—C18	117.11 (17)
H14A—C14—H14B	108.4	C20—O10—C21	109.93 (14)
C14—C15—H15A	109.5

O1—C2—C3—C4	177.5 (2)	C16—C12—N2—C10	−6.52 (18)
C7—C2—C3—C4	−1.5 (3)	N3—C12—N2—C8	−51.4 (2)
C2—C3—C4—C5	−2.6 (4)	C13—C12—N2—C8	75.16 (19)
C3—C4—C5—C6	3.5 (3)	C16—C12—N2—C8	−162.06 (14)
C3—C4—C5—N1	−177.9 (2)	C7—C8—N2—C10	−75.8 (2)
C4—C5—C6—C7	−0.2 (3)	C7—C8—N2—C12	77.7 (2)
N1—C5—C6—C7	−178.78 (18)	O5—C11—N3—C12	163.25 (17)
C4—C5—C6—C9	174.65 (19)	N5—C11—N3—C12	−18.73 (19)
N1—C5—C6—C9	−3.9 (3)	O5—C11—N3—C9	14.2 (3)
C5—C6—C7—C2	−3.8 (3)	N5—C11—N3—C9	−167.75 (14)
C9—C6—C7—C2	−178.99 (17)	N2—C12—N3—C11	−95.88 (17)
C5—C6—C7—C8	172.41 (17)	C13—C12—N3—C11	139.01 (15)
C9—C6—C7—C8	−2.8 (3)	C16—C12—N3—C11	14.39 (17)
O1—C2—C7—C6	−174.30 (16)	N2—C12—N3—C9	51.5 (2)
C3—C2—C7—C6	4.8 (3)	C13—C12—N3—C9	−73.64 (19)
O1—C2—C7—C8	9.4 (3)	C16—C12—N3—C9	161.74 (14)
C3—C2—C7—C8	−171.46 (18)	C6—C9—N3—C11	66.5 (2)
C6—C7—C8—N2	−63.0 (2)	C6—C9—N3—C12	−79.0 (2)
C2—C7—C8—N2	113.21 (19)	O4—C10—N4—C16	167.50 (17)
C5—C6—C9—N3	−108.2 (2)	N2—C10—N4—C16	−15.36 (18)
C7—C6—C9—N3	66.6 (2)	O4—C10—N4—C20	29.5 (3)
N3—C12—C13—O6	13.8 (3)	N2—C10—N4—C20	−153.33 (15)
N2—C12—C13—O6	−113.9 (2)	N5—C16—N4—C10	−99.68 (16)
C16—C12—C13—O6	131.4 (2)	C17—C16—N4—C10	137.58 (15)
N3—C12—C13—O7	−166.84 (15)	C12—C16—N4—C10	10.84 (17)
N2—C12—C13—O7	65.42 (18)	N5—C16—N4—C20	39.8 (2)
C16—C12—C13—O7	−49.3 (2)	C17—C16—N4—C20	−82.92 (18)
N3—C12—C16—N4	−121.48 (13)	C12—C16—N4—C20	150.34 (14)
N2—C12—C16—N4	−2.63 (16)	O10—C20—N4—C10	84.80 (19)
C13—C12—C16—N4	116.05 (15)	O10—C20—N4—C16	−51.2 (2)
N3—C12—C16—N5	−4.92 (16)	O5—C11—N5—C21	−23.8 (3)
N2—C12—C16—N5	113.93 (14)	N3—C11—N5—C21	158.19 (15)
C13—C12—C16—N5	−127.39 (15)	O5—C11—N5—C16	−167.04 (17)
N3—C12—C16—C17	115.40 (16)	N3—C11—N5—C16	14.96 (19)
N2—C12—C16—C17	−125.75 (15)	O10—C21—N5—C11	−90.42 (19)
C13—C12—C16—C17	−7.1 (2)	O10—C21—N5—C16	51.0 (2)
N4—C16—C17—O8	2.5 (3)	N4—C16—N5—C11	105.40 (16)
N5—C16—C17—O8	−121.3 (2)	C17—C16—N5—C11	−130.93 (15)
C12—C16—C17—O8	121.9 (2)	C12—C16—N5—C11	−5.74 (17)
N4—C16—C17—O9	−179.71 (15)	N4—C16—N5—C21	−40.1 (2)
N5—C16—C17—O9	56.45 (19)	C17—C16—N5—C21	83.56 (18)
C12—C16—C17—O9	−60.3 (2)	C12—C16—N5—C21	−151.25 (15)
C4—C5—N1—O2	135.0 (2)	C3—C2—O1—C1	8.2 (3)
C6—C5—N1—O2	−46.4 (3)	C7—C2—O1—C1	−172.69 (19)
C4—C5—N1—O3	−42.5 (3)	O6—C13—O7—C14	−3.2 (3)
C6—C5—N1—O3	136.1 (2)	C12—C13—O7—C14	177.43 (18)
O4—C10—N2—C12	−169.24 (17)	C15—C14—O7—C13	−166.0 (2)
N4—C10—N2—C12	13.63 (19)	O8—C17—O9—C18	4.9 (3)
O4—C10—N2—C8	−13.5 (3)	C16—C17—O9—C18	−172.78 (17)
N4—C10—N2—C8	169.41 (14)	C19—C18—O9—C17	86.1 (3)
N3—C12—N2—C10	104.18 (17)	N4—C20—O10—C21	60.3 (2)
C13—C12—N2—C10	−129.30 (15)	N5—C21—O10—C20	−60.17 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O10ⁱ	0.93	2.50	3.342 (3)	150
C21—H21A···O5ⁱⁱ	0.97	2.31	3.233 (2)	158
C18—H18A···O2ⁱⁱⁱ	0.97	2.56	3.343 (3)	138
C14—H14B···O2ⁱⁱⁱ	0.97	2.57	3.519 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₃N₅O₁₀
M_r	505.44
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	9.756 (2), 10.608 (2), 11.716 (3)
α, β, γ (°)	110.123 (4), 98.754 (4), 92.119 (4)
V (Å³)	1119.9 (4)
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 CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8700, 4340, 3412
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.06
No. of reflections	4340
No. of parameters	328
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

C2—C3	1.383 (3)	C10—N4	1.390 (2)
C2—C7	1.404 (3)	C12—N2	1.453 (2)
C7—C8	1.517 (3)	C12—C16	1.571 (2)
C8—N2	1.463 (2)	C16—N4	1.444 (2)
C10—O4	1.205 (2)	C20—N4	1.452 (2)
C10—N2	1.369 (2)	C21—O10	1.423 (2)

C2—C7—C8	119.94 (17)	N2—C12—C16	102.39 (13)
N2—C8—C7	112.31 (14)	O10—C20—N4	110.87 (15)
N2—C10—N4	108.27 (14)