(E)-1-(2,4-Dinitro­phen­yl)-2-{2-[2-(3-nitrophen­oxy)eth­oxy]benzyl­idene}hydrazine dimethyl­formamide solvate

Diao, C.-H.; Fan, Z.; Yu, M.; Chen, X.; Jing, Z.-L.

doi:10.1107/S1600536805039905

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(E)-1-(2,4-Dinitrophenyl)-2-{2-[2-(3-nitrophenoxy)ethoxy]benzylidene}hydrazine dimethylformamide solvate

C.-H. Diao, Z. Fan, M. Yu, X. Chen and Z.-L. Jing

The molecule of the title compound, C₂₁H₁₇N₅O₈·C₃H₇NO, is non-planar. The central benzene ring makes dihedral angles of 86.87 (8) and 4.52 (6)° with the terminal benzene ring bonded to the ethoxy functionality and the p-nitrophenyl residue bonded to the hydrazine functionality, respectively. Intramolecular N—H

O and C—H

O hydrogen bonds help to stabilize the molecular conformation, while weak intermolecular C—H

O hydrogen bonds link adjacent molecules to form infinite chains in the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039905/bh6053sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039905/bh6053Isup2.hkl Contains datablock I

CCDC reference: 296521

checkCIF report

Key indicators

Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.003 Å
R factor = 0.052
wR factor = 0.136
Data-to-parameter ratio = 14.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N5     -   C19     ..       5.70 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for         N6
PLAT480_ALERT_4_C Long H...A H-Bond Reported H10    ..  O7      ..       2.61 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Metal complexes based on Schiff bases have been extensively studied, because of their significant biological activity (Kahwa et al., 1986). Consequently, significant effort has been devoted to the synthesis of Schiff base derivatives to develop protein and enzyme mimics (Pires Santos et al., 2001). In order to investigate their crystal structures, which will provide useful information for the coordination properties of Schiff bases functioning as ligands, we report the synthesis and structure of the title dinitrophenylhydrazine Schiff base derivative, (I).

The central benzene ring of (I) (atoms C9–C14) is almost perpendicular to the terminal benzene ring bonded to the ethoxy functionality (C1–C6), with a dihedral angle of 86.87 (8)° (Fig. 1). The p-nitrophenyl residue (C16–C21/N5/O7/O8) bonded to the hydrazine functionality is planar, with an r.m.s. deviation of the fitted atoms of 0.010 Å. This plane makes dihedral angles of 87.56 (6) and 4.52 (6)° with the terminal benzene ring (C1–C6) and the central benzene ring (C9–C14), respectively. The O7—N5—C19—C18 and O8—N5—C19—C20 torsion angles are 179.3 (2) and 179.8 (2)°, respectively, confirming the coplanarity of the nitro group (N5/O7/O8) with the aromatic ring (C16–C21). The corresponding dihedral angle is indeed virtually zero, at 1.0 (3)°. The other nitro group (N4/O5/O6) makes a dihedral angle of 2.26 (11)° with the same ring. All bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987).

An intramolecular N3—H3···O5 hydrogen bond is found in (I) (Table 1), which helps to stabilize the conformation of the molecule. There is also a weak C15—H15···O9 hydrogen bond linking the main molecule and the solvent molecule. The packing structure is stabilized by a couple of weak non-classical intermolecular C—H···O hydrogen bonds (Table 1), forming infinite chains in the crystal structure (Fig. 2).

Experimental top

To a solution of 2-hydroxybenzaldehyde (6.1 g, 50 mmol) and potassium carbonate (13.8 g, 100 mmol) in acetonitrile (500 ml), 1-bromo-2-chloroethane (7.1 g, 50 mmol) was added dropwise over a period of 30 min and the mixture refluxed for 24 h under an N₂ atmosphere. 3-Nitrophenol (7.0 g, 50 mmol) dissolved in acetonitrile (100 ml) was then added dropwise over a period of 30 min and the mixture was refluxed for an additional 48 h under an N₂ atmosphere. The solvent was then removed and the resulting mixture poured into ice–water (500 ml). The white precipitate which formed was isolated and recrystallized from ethanol to give pure 2-[2-(3-nitrophenoxy)ethoxy]benzaldehyde in 26% yield. An anhydrous ethanol solution of 2-[2-(3-nitrophenoxy)ethoxy]benzaldehyde (2.87 g, 10 mmol) was added to an anhydrous ethanol solution of 1-(2,4-dinitrophenyl)hydrazine (1.98 g, 10 mmol) and the mixture stirred at 350 K for 5 h under N₂, whereupon an orange precipitate appeared. The product was isolated, recrystallized from acetonitrile and dried in vacuo, to give pure (I) in 88% yield. Orange single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an N,N-dimethylformamide solution over a period of 20 d.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram for (I), with hydrogen bonds drawn as dashed lines.

(E)-1-(2,4-Dinitrophenyl)-2-{2-[2-(3-nitrophenoxy)ethoxy]benzylidene}hydrazine dimethylformamide solvate top

Crystal data top

C₂₁H₁₇N₅O₈·C₃H₇NO	F(000) = 1128
M_r = 540.49	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2554 reflections
a = 6.9806 (12) Å	θ = 2.8–25.9°
b = 25.764 (4) Å	µ = 0.11 mm⁻¹
c = 14.200 (2) Å	T = 294 K
β = 96.318 (3)°	Block, orange
V = 2538.4 (7) Å³	0.28 × 0.24 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5198 independent reflections
Radiation source: fine-focus sealed tube	2638 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
T_min = 0.920, T_max = 0.978	k = −32→31
14295 measured reflections	l = −17→9

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0581P)² + 0.0615P] where P = (F_o² + 2F_c²)/3
5198 reflections	(Δ/σ)_max = 0.005
354 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₁H₁₇N₅O₈·C₃H₇NO	V = 2538.4 (7) Å³
M_r = 540.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.9806 (12) Å	µ = 0.11 mm⁻¹
b = 25.764 (4) Å	T = 294 K
c = 14.200 (2) Å	0.28 × 0.24 × 0.20 mm
β = 96.318 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5198 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2638 reflections with I > 2σ(I)
T_min = 0.920, T_max = 0.978	R_int = 0.049
14295 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
5198 reflections	Δρ_min = −0.20 e Å⁻³
354 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 > 2σ(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
O1	0.1028 (4)	0.57277 (9)	0.9188 (2)	0.1156 (10)
O2	0.3452 (4)	0.62265 (8)	0.90703 (17)	0.0990 (8)
O3	0.3689 (2)	0.39340 (6)	0.88964 (12)	0.0545 (5)
O4	0.1279 (2)	0.30398 (6)	0.85839 (10)	0.0470 (4)
O5	−0.2561 (3)	0.38877 (7)	0.48617 (14)	0.0731 (6)
O6	−0.3805 (4)	0.40262 (7)	0.34368 (15)	0.0965 (8)
O7	−0.5730 (3)	0.27007 (9)	0.12872 (13)	0.0728 (6)
O8	−0.5455 (3)	0.18964 (9)	0.16958 (13)	0.0798 (6)
N1	0.2690 (5)	0.57986 (10)	0.90446 (18)	0.0729 (7)
N2	−0.1132 (3)	0.25514 (7)	0.60742 (13)	0.0389 (5)
N3	−0.1890 (3)	0.29379 (7)	0.54759 (12)	0.0386 (5)
H3	−0.1813	0.3257	0.5652	0.046*
N4	−0.3239 (3)	0.37282 (8)	0.40798 (17)	0.0551 (6)
N5	−0.5265 (3)	0.23574 (10)	0.18659 (15)	0.0536 (6)
C1	0.3119 (4)	0.48604 (9)	0.89723 (16)	0.0455 (6)
H1	0.1930	0.4820	0.9200	0.055*
C2	0.3852 (4)	0.53483 (9)	0.88229 (17)	0.0508 (7)
C3	0.5581 (5)	0.54309 (11)	0.84935 (19)	0.0615 (8)
H3A	0.6033	0.5765	0.8407	0.074*
C4	0.6644 (4)	0.50009 (12)	0.8292 (2)	0.0655 (8)
H4	0.7832	0.5045	0.8064	0.079*
C5	0.5969 (4)	0.45088 (10)	0.84246 (19)	0.0596 (8)
H5	0.6696	0.4223	0.8280	0.071*
C6	0.4210 (4)	0.44353 (9)	0.87725 (16)	0.0445 (6)
C7	0.1985 (4)	0.38345 (9)	0.93452 (18)	0.0495 (7)
H7A	0.0854	0.3956	0.8948	0.059*
H7B	0.2052	0.4013	0.9949	0.059*
C8	0.1871 (4)	0.32635 (9)	0.94896 (15)	0.0455 (6)
H8A	0.3119	0.3128	0.9743	0.055*
H8B	0.0945	0.3184	0.9930	0.055*
C9	0.1219 (3)	0.25128 (9)	0.84883 (15)	0.0365 (5)
C10	0.1864 (3)	0.21659 (9)	0.92021 (16)	0.0427 (6)
H10	0.2342	0.2287	0.9799	0.051*
C11	0.1789 (4)	0.16436 (10)	0.90179 (18)	0.0501 (7)
H11	0.2207	0.1411	0.9497	0.060*
C12	0.1102 (4)	0.14574 (9)	0.81326 (19)	0.0532 (7)
H12	0.1101	0.1103	0.8012	0.064*
C13	0.0419 (3)	0.18002 (9)	0.74298 (17)	0.0441 (6)
H13	−0.0061	0.1674	0.6837	0.053*
C14	0.0440 (3)	0.23337 (8)	0.75973 (15)	0.0351 (5)
C15	−0.0363 (3)	0.27046 (9)	0.68894 (15)	0.0378 (6)
H15	−0.0319	0.3057	0.7029	0.045*
C16	−0.2756 (3)	0.28095 (8)	0.46096 (15)	0.0328 (5)
C17	−0.3073 (3)	0.22854 (9)	0.43651 (16)	0.0395 (6)
H17	−0.2720	0.2031	0.4815	0.047*
C18	−0.3878 (3)	0.21401 (9)	0.34914 (16)	0.0422 (6)
H18	−0.4074	0.1790	0.3350	0.051*
C19	−0.4409 (3)	0.25149 (10)	0.28090 (15)	0.0399 (6)
C20	−0.4180 (3)	0.30278 (9)	0.30103 (16)	0.0416 (6)
H20	−0.4557	0.3276	0.2551	0.050*
C21	−0.3383 (3)	0.31794 (8)	0.39026 (15)	0.0369 (6)
O9	−0.0494 (4)	0.40305 (9)	0.69916 (19)	0.1115 (9)
N6	0.1713 (4)	0.45169 (10)	0.63236 (18)	0.0768 (8)
C22	0.1049 (6)	0.40784 (14)	0.6656 (3)	0.0893 (11)
H22	0.1812	0.3784	0.6634	0.107*
C23	0.3551 (6)	0.45456 (16)	0.5973 (3)	0.1173 (14)
H23A	0.4326	0.4804	0.6322	0.176*
H23B	0.3381	0.4638	0.5314	0.176*
H23C	0.4180	0.4215	0.6047	0.176*
C24	0.0549 (7)	0.49820 (13)	0.6358 (3)	0.1208 (15)
H24A	−0.0764	0.4886	0.6410	0.181*
H24B	0.0612	0.5180	0.5790	0.181*
H24C	0.1030	0.5187	0.6897	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.102 (2)	0.0717 (17)	0.180 (3)	0.0275 (16)	0.045 (2)	0.0008 (15)
O2	0.135 (2)	0.0456 (13)	0.112 (2)	0.0045 (14)	−0.0084 (15)	−0.0110 (12)
O3	0.0558 (12)	0.0400 (10)	0.0708 (13)	−0.0007 (8)	0.0213 (9)	−0.0056 (8)
O4	0.0639 (12)	0.0412 (10)	0.0338 (10)	−0.0060 (8)	−0.0045 (8)	0.0006 (7)
O5	0.1153 (18)	0.0451 (11)	0.0545 (13)	−0.0002 (11)	−0.0108 (11)	−0.0054 (9)
O6	0.149 (2)	0.0464 (12)	0.0824 (16)	−0.0004 (12)	−0.0387 (14)	0.0212 (11)
O7	0.0740 (15)	0.1008 (16)	0.0404 (12)	−0.0017 (12)	−0.0079 (9)	0.0062 (11)
O8	0.1045 (18)	0.0769 (15)	0.0566 (13)	−0.0332 (13)	0.0032 (11)	−0.0189 (11)
N1	0.097 (2)	0.0460 (16)	0.0729 (18)	0.0135 (16)	−0.0043 (16)	0.0012 (12)
N2	0.0409 (12)	0.0430 (11)	0.0319 (11)	0.0011 (9)	0.0010 (9)	0.0047 (9)
N3	0.0467 (12)	0.0362 (11)	0.0319 (11)	−0.0010 (9)	0.0000 (9)	0.0020 (9)
N4	0.0667 (16)	0.0438 (13)	0.0523 (15)	0.0015 (11)	−0.0053 (12)	0.0082 (12)
N5	0.0469 (14)	0.0755 (17)	0.0388 (14)	−0.0132 (12)	0.0063 (10)	−0.0030 (13)
C1	0.0473 (16)	0.0473 (15)	0.0415 (15)	0.0026 (12)	0.0025 (11)	−0.0037 (12)
C2	0.0639 (19)	0.0410 (15)	0.0450 (17)	0.0071 (14)	−0.0052 (13)	−0.0016 (12)
C3	0.077 (2)	0.0519 (18)	0.0539 (19)	−0.0104 (16)	−0.0016 (15)	0.0077 (13)
C4	0.062 (2)	0.070 (2)	0.068 (2)	−0.0091 (17)	0.0191 (15)	0.0023 (15)
C5	0.061 (2)	0.0522 (17)	0.069 (2)	0.0006 (14)	0.0188 (15)	−0.0019 (13)
C6	0.0490 (16)	0.0411 (15)	0.0430 (16)	−0.0020 (12)	0.0031 (12)	−0.0020 (11)
C7	0.0482 (17)	0.0528 (16)	0.0480 (17)	−0.0018 (12)	0.0074 (12)	−0.0103 (12)
C8	0.0490 (16)	0.0556 (16)	0.0312 (14)	−0.0055 (12)	0.0013 (11)	−0.0049 (12)
C9	0.0328 (13)	0.0403 (14)	0.0366 (14)	−0.0023 (11)	0.0043 (10)	0.0042 (11)
C10	0.0389 (15)	0.0537 (16)	0.0354 (14)	−0.0024 (12)	0.0041 (11)	0.0074 (12)
C11	0.0473 (16)	0.0498 (17)	0.0529 (18)	0.0049 (13)	0.0042 (13)	0.0169 (13)
C12	0.0582 (18)	0.0374 (15)	0.064 (2)	0.0034 (12)	0.0084 (14)	0.0043 (13)
C13	0.0460 (16)	0.0433 (15)	0.0428 (15)	−0.0003 (12)	0.0032 (11)	0.0005 (12)
C14	0.0348 (14)	0.0402 (14)	0.0303 (13)	−0.0031 (10)	0.0039 (10)	0.0040 (10)
C15	0.0387 (14)	0.0415 (14)	0.0329 (14)	−0.0077 (11)	0.0026 (11)	0.0007 (11)
C16	0.0320 (13)	0.0387 (13)	0.0284 (13)	−0.0031 (10)	0.0062 (10)	0.0009 (10)
C17	0.0397 (15)	0.0419 (14)	0.0363 (15)	−0.0046 (11)	0.0018 (11)	0.0043 (11)
C18	0.0432 (15)	0.0420 (14)	0.0419 (16)	−0.0079 (11)	0.0065 (11)	−0.0029 (12)
C19	0.0365 (14)	0.0557 (16)	0.0272 (13)	−0.0083 (12)	0.0023 (10)	−0.0014 (11)
C20	0.0350 (14)	0.0542 (16)	0.0351 (14)	−0.0008 (12)	0.0027 (11)	0.0109 (11)
C21	0.0361 (14)	0.0383 (14)	0.0362 (14)	−0.0007 (10)	0.0031 (10)	0.0045 (11)
O9	0.112 (2)	0.1007 (19)	0.124 (2)	0.0024 (16)	0.0246 (18)	0.0270 (15)
N6	0.094 (2)	0.0671 (18)	0.0702 (19)	−0.0114 (16)	0.0127 (15)	−0.0030 (13)
C22	0.101 (3)	0.072 (3)	0.094 (3)	0.008 (2)	0.008 (2)	0.002 (2)
C23	0.113 (4)	0.139 (4)	0.102 (3)	−0.030 (3)	0.023 (3)	−0.022 (2)
C24	0.166 (4)	0.066 (2)	0.133 (4)	0.010 (3)	0.029 (3)	0.017 (2)

Geometric parameters (Å, º) top

O1—N1	1.213 (3)	C9—C10	1.389 (3)
O2—N1	1.223 (3)	C9—C14	1.399 (3)
O3—C6	1.358 (3)	C10—C11	1.371 (3)
O3—C7	1.433 (3)	C10—H10	0.9300
O4—C9	1.365 (3)	C11—C12	1.381 (3)
O4—C8	1.428 (3)	C11—H11	0.9300
O5—N4	1.229 (3)	C12—C13	1.378 (3)
O6—N4	1.225 (3)	C12—H12	0.9300
O7—N5	1.227 (3)	C13—C14	1.395 (3)
O8—N5	1.216 (3)	C13—H13	0.9300
N1—C2	1.469 (3)	C14—C15	1.454 (3)
N2—C15	1.283 (3)	C15—H15	0.9300
N2—N3	1.377 (2)	C16—C17	1.406 (3)
N3—C16	1.351 (3)	C16—C21	1.418 (3)
N3—H3	0.8600	C17—C18	1.357 (3)
N4—C21	1.438 (3)	C17—H17	0.9300
N5—C19	1.463 (3)	C18—C19	1.389 (3)
C1—C6	1.381 (3)	C18—H18	0.9300
C1—C2	1.382 (3)	C19—C20	1.358 (3)
C1—H1	0.9300	C20—C21	1.383 (3)
C2—C3	1.359 (4)	C20—H20	0.9300
C3—C4	1.381 (4)	O9—C22	1.231 (4)
C3—H3A	0.9300	N6—C22	1.327 (4)
C4—C5	1.373 (4)	N6—C23	1.428 (4)
C4—H4	0.9300	N6—C24	1.451 (4)
C5—C6	1.386 (3)	C22—H22	0.9300
C5—H5	0.9300	C23—H23A	0.9600
C7—C8	1.489 (3)	C23—H23B	0.9600
C7—H7A	0.9700	C23—H23C	0.9600
C7—H7B	0.9700	C24—H24A	0.9600
C8—H8A	0.9700	C24—H24B	0.9600
C8—H8B	0.9700	C24—H24C	0.9600

C6—O3—C7	118.32 (18)	C10—C11—C12	121.1 (2)
C9—O4—C8	119.58 (17)	C10—C11—H11	119.4
O1—N1—O2	123.5 (3)	C12—C11—H11	119.4
O1—N1—C2	118.5 (3)	C13—C12—C11	119.6 (2)
O2—N1—C2	118.0 (3)	C13—C12—H12	120.2
C15—N2—N3	115.36 (18)	C11—C12—H12	120.2
C16—N3—N2	119.21 (18)	C12—C13—C14	120.8 (2)
C16—N3—H3	120.4	C12—C13—H13	119.6
N2—N3—H3	120.4	C14—C13—H13	119.6
O6—N4—O5	121.6 (2)	C13—C14—C9	118.3 (2)
O6—N4—C21	118.4 (2)	C13—C14—C15	122.3 (2)
O5—N4—C21	120.0 (2)	C9—C14—C15	119.4 (2)
O8—N5—O7	123.8 (2)	N2—C15—C14	120.8 (2)
O8—N5—C19	118.5 (2)	N2—C15—H15	119.6
O7—N5—C19	117.7 (2)	C14—C15—H15	119.6
C6—C1—C2	117.9 (2)	N3—C16—C17	120.18 (19)
C6—C1—H1	121.0	N3—C16—C21	123.54 (19)
C2—C1—H1	121.0	C17—C16—C21	116.3 (2)
C3—C2—C1	123.6 (2)	C18—C17—C16	121.9 (2)
C3—C2—N1	118.8 (3)	C18—C17—H17	119.0
C1—C2—N1	117.6 (3)	C16—C17—H17	119.0
C2—C3—C4	117.7 (3)	C17—C18—C19	119.8 (2)
C2—C3—H3A	121.2	C17—C18—H18	120.1
C4—C3—H3A	121.2	C19—C18—H18	120.1
C5—C4—C3	120.8 (3)	C20—C19—C18	120.9 (2)
C5—C4—H4	119.6	C20—C19—N5	119.3 (2)
C3—C4—H4	119.6	C18—C19—N5	119.8 (2)
C4—C5—C6	120.4 (3)	C19—C20—C21	119.6 (2)
C4—C5—H5	119.8	C19—C20—H20	120.2
C6—C5—H5	119.8	C21—C20—H20	120.2
O3—C6—C1	124.5 (2)	C20—C21—C16	121.4 (2)
O3—C6—C5	115.8 (2)	C20—C21—N4	116.8 (2)
C1—C6—C5	119.7 (2)	C16—C21—N4	121.8 (2)
O3—C7—C8	107.30 (19)	C22—N6—C23	122.0 (3)
O3—C7—H7A	110.3	C22—N6—C24	118.2 (3)
C8—C7—H7A	110.3	C23—N6—C24	119.8 (3)
O3—C7—H7B	110.3	O9—C22—N6	125.3 (4)
C8—C7—H7B	110.3	O9—C22—H22	117.4
H7A—C7—H7B	108.5	N6—C22—H22	117.4
O4—C8—C7	106.81 (19)	N6—C23—H23A	109.5
O4—C8—H8A	110.4	N6—C23—H23B	109.5
C7—C8—H8A	110.4	H23A—C23—H23B	109.5
O4—C8—H8B	110.4	N6—C23—H23C	109.5
C7—C8—H8B	110.4	H23A—C23—H23C	109.5
H8A—C8—H8B	108.6	H23B—C23—H23C	109.5
O4—C9—C10	124.3 (2)	N6—C24—H24A	109.5
O4—C9—C14	115.00 (19)	N6—C24—H24B	109.5
C10—C9—C14	120.7 (2)	H24A—C24—H24B	109.5
C11—C10—C9	119.3 (2)	N6—C24—H24C	109.5
C11—C10—H10	120.3	H24A—C24—H24C	109.5
C9—C10—H10	120.3	H24B—C24—H24C	109.5

C15—N2—N3—C16	−178.9 (2)	O4—C9—C14—C15	−4.8 (3)
C6—C1—C2—C3	−0.2 (4)	C10—C9—C14—C15	175.1 (2)
C6—C1—C2—N1	−179.5 (2)	N3—N2—C15—C14	178.20 (18)
O1—N1—C2—C3	168.1 (3)	C13—C14—C15—N2	0.1 (3)
O2—N1—C2—C3	−11.6 (4)	C9—C14—C15—N2	−178.2 (2)
O1—N1—C2—C1	−12.5 (4)	N2—N3—C16—C17	7.2 (3)
O2—N1—C2—C1	167.8 (2)	N2—N3—C16—C21	−172.49 (19)
C1—C2—C3—C4	0.6 (4)	N3—C16—C17—C18	−177.7 (2)
N1—C2—C3—C4	179.9 (2)	C21—C16—C17—C18	2.0 (3)
C2—C3—C4—C5	−0.2 (4)	C16—C17—C18—C19	0.2 (3)
C3—C4—C5—C6	−0.6 (4)	C17—C18—C19—C20	−1.7 (3)
C7—O3—C6—C1	−6.1 (3)	C17—C18—C19—N5	179.6 (2)
C7—O3—C6—C5	173.6 (2)	O8—N5—C19—C20	179.8 (2)
C2—C1—C6—O3	179.1 (2)	O7—N5—C19—C20	0.6 (3)
C2—C1—C6—C5	−0.6 (3)	O8—N5—C19—C18	−1.5 (3)
C4—C5—C6—O3	−178.7 (2)	O7—N5—C19—C18	179.3 (2)
C4—C5—C6—C1	1.0 (4)	C18—C19—C20—C21	0.9 (3)
C6—O3—C7—C8	−173.75 (19)	N5—C19—C20—C21	179.6 (2)
C9—O4—C8—C7	174.20 (18)	C19—C20—C21—C16	1.4 (3)
O3—C7—C8—O4	−74.6 (2)	C19—C20—C21—N4	−178.0 (2)
C8—O4—C9—C10	−6.0 (3)	N3—C16—C21—C20	176.9 (2)
C8—O4—C9—C14	173.93 (19)	C17—C16—C21—C20	−2.8 (3)
O4—C9—C10—C11	−178.0 (2)	N3—C16—C21—N4	−3.7 (3)
C14—C9—C10—C11	2.1 (3)	C17—C16—C21—N4	176.58 (19)
C9—C10—C11—C12	0.7 (3)	O6—N4—C21—C20	−0.7 (3)
C10—C11—C12—C13	−2.2 (4)	O5—N4—C21—C20	179.3 (2)
C11—C12—C13—C14	1.0 (4)	O6—N4—C21—C16	179.9 (2)
C12—C13—C14—C9	1.7 (3)	O5—N4—C21—C16	−0.1 (3)
C12—C13—C14—C15	−176.6 (2)	C23—N6—C22—O9	177.9 (4)
O4—C9—C14—C13	176.81 (19)	C24—N6—C22—O9	0.4 (6)
C10—C9—C14—C13	−3.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5	0.86	2.01	2.623 (3)	127
C15—H15···O9	0.93	2.51	3.421 (3)	166
C8—H8A···O7ⁱ	0.97	2.51	3.237 (3)	132
C10—H10···O7ⁱ	0.93	2.61	3.520 (3)	168

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

Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₅O₈·C₃H₇NO
M_r	540.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	6.9806 (12), 25.764 (4), 14.200 (2)
β (°)	96.318 (3)
V (Å³)	2538.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.920, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14295, 5198, 2638
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.136, 1.00
No. of reflections	5198
No. of parameters	354
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O5	0.86	2.01	2.623 (3)	127
C15—H15···O9	0.93	2.51	3.421 (3)	166
C8—H8A···O7ⁱ	0.97	2.51	3.237 (3)	132
C10—H10···O7ⁱ	0.93	2.61	3.520 (3)	168

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

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