2,6-Bis(4,6-dimethoxy­pyrimidin-2-yl­oxy)benzoic acid

Chopra, D.; Mohan, T.P.; Vishalakshi, B.; Guru Row, T.N.

doi:10.1107/S160053680502859X

2,6-Bis(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid

D. Chopra, T. P. Mohan, B. Vishalakshi and T. N. Guru Row

The title compound, C₁₉H₁₈N₄O₈, belonging to the pyrimidinyloxybenzoic acid family, exhibits herbicidal properties. The crystal structure is stabilized by C—H

O and O—H

N intermolecular hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680502859X/ob6586sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680502859X/ob6586Isup2.hkl Contains datablock I

CCDC reference: 287686

checkCIF report

Key indicators

Single-crystal X-ray study
T = 290 K
Mean (C-C) = 0.004 Å
R factor = 0.065
wR factor = 0.158
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT022_ALERT_3_B Ratio Unique / Expected Reflections too Low ....       0.89

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.60 Ratio

   0 ALERT level A = In general: serious problem
   1 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

An important aspect in the rational design of bioactive molecules involves relating chemical structure to biological activity (Lewis et al., 1991). The conformation of the molecule is found to influence the levels of biological activity. Correlation of the results obtained from X-ray crystallography with biological activity has aided in the chemical design of few active agrochemicals. The activity of a series of triazolyl ketone herbicides (Anderson et al., 1983) has been investigated along with the fungicidal activities of N-phenyl succinamides (Zenei et al., 1988). In this paper, we report the structure of the title compound, (I), which is a selective, systemic post-emergence herbicide used for the control of a wide range of weeds.

Fig. 1 shows an ORTEP-3 (Farrugia, 1997) view of the compound. The methoxy groups move away from each other to minimize steric repulsions between the non-bonded H atoms, but lie nearly on the plane of the pyrimidine ring. The pyrimidine rings (C1/N1/C3–C5/N2 and C22/N3/C10–C12/N4) make dihedral angles of 85.2 (1) and 60.9 (1)°, respectively, with the plane of the benzene ring. The difference in bond lengths involving atoms O1 and O10 indicates that the electronic environment is different (Table 1). The H atom of the carboxylic group is not involved in the formation of `classical carboxylic acid dimers'. Instead it forms a hydrogen bond (Table 2 and Fig. 2) with the pyrimidiyl N atom, forming ring dimers [Etter's symbol R₂²(16); Bernstein et al., 1995]. Atom O7 is also involved in the formation of dimeric motifs via the C—H···O interactions [Etter's symbol R₂²(20)].

Experimental top

Compound (I) was supplied by Rallis India Limited. Crystals were grown by slow evaporation from a solution of methanol at 278 K.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare, 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), showing 50% ellipsoidal probability.
	Fig. 2. Packing diagram of (I). Dotted lines indicate O—H···N and C—H···O interactions. H atoms have been omitted for clarity, except for those involved in the hydrogen bonds. The symbols ' and " refer to the symmetry codes (1 − x, −y, 1 − z) and (−x, 1 − y, 1 − z), respectively.

2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid top

Crystal data top

C₁₉H₁₈N₄O₈	Z = 2
M_r = 430.37	F(000) = 448
Triclinic, P1	D_x = 1.420 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7779 (12) Å	Cell parameters from 765 reflections
b = 8.2973 (13) Å	θ = 1.4–25.4°
c = 16.883 (3) Å	µ = 0.11 mm⁻¹
α = 87.899 (3)°	T = 290 K
β = 79.054 (3)°	Plate, colorless
γ = 70.276 (3)°	0.40 × 0.30 × 0.04 mm
V = 1006.5 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4089 independent reflections
Radiation source: fine-focus sealed tube	2777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 27.4°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.947, T_max = 0.996	k = −10→10
8103 measured reflections	l = −21→21

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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.072P)²] where P = (F_o² + 2F_c²)/3
4089 reflections	(Δ/σ)_max < 0.001
308 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₉H₁₈N₄O₈	γ = 70.276 (3)°
M_r = 430.37	V = 1006.5 (3) Å³
Triclinic, P1	Z = 2
a = 7.7779 (12) Å	Mo Kα radiation
b = 8.2973 (13) Å	µ = 0.11 mm⁻¹
c = 16.883 (3) Å	T = 290 K
α = 87.899 (3)°	0.40 × 0.30 × 0.04 mm
β = 79.054 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4089 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2777 reflections with I > 2σ(I)
T_min = 0.947, T_max = 0.996	R_int = 0.023
8103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	Δρ_max = 0.22 e Å⁻³
4089 reflections	Δρ_min = −0.19 e Å⁻³
308 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
O1	0.2858 (3)	0.3742 (2)	0.17593 (11)	0.0484 (5)
O2	0.5676 (3)	−0.1994 (3)	0.10678 (14)	0.0718 (7)
O3	0.8314 (3)	0.2081 (3)	0.00026 (14)	0.0743 (7)
O4	0.3898 (3)	−0.1557 (2)	0.47309 (13)	0.0586 (6)
O5	0.0369 (3)	0.2235 (3)	0.69249 (12)	0.0590 (6)
O6	0.3037 (3)	0.4375 (3)	0.39396 (12)	0.0509 (5)
O7	0.4594 (2)	0.2207 (2)	0.30927 (12)	0.0494 (5)
O10	−0.0540 (2)	0.3640 (2)	0.44452 (10)	0.0418 (5)
N1	0.4145 (3)	0.0856 (3)	0.14356 (13)	0.0460 (6)
N2	0.5543 (3)	0.2926 (3)	0.09031 (13)	0.0456 (6)
N3	0.1692 (3)	0.0995 (3)	0.45291 (13)	0.0385 (5)
N4	−0.0011 (3)	0.2845 (3)	0.56659 (13)	0.0380 (5)
C1	0.4248 (4)	0.2410 (3)	0.13521 (16)	0.0418 (6)
C3	0.5609 (4)	−0.0349 (4)	0.10135 (18)	0.0518 (7)
C4	0.7065 (5)	−0.0022 (4)	0.0524 (2)	0.0619 (9)
C5	0.6946 (4)	0.1674 (4)	0.04872 (17)	0.0522 (8)
C7	0.4196 (6)	−0.2354 (4)	0.1598 (2)	0.0848 (12)
C8	0.8070 (4)	0.3865 (4)	−0.0098 (2)	0.0731 (10)
C10	0.2601 (3)	−0.0086 (3)	0.50329 (17)	0.0420 (7)
C11	0.2290 (4)	0.0197 (3)	0.58577 (18)	0.0442 (7)
C12	0.0934 (4)	0.1704 (3)	0.61511 (16)	0.0413 (6)
C14	0.4240 (4)	−0.1888 (4)	0.3875 (2)	0.0625 (9)
C15	0.1209 (5)	0.1149 (5)	0.75242 (19)	0.0781 (11)
C16	0.1349 (4)	0.3477 (3)	0.22807 (16)	0.0402 (6)
C17	−0.0198 (4)	0.3562 (4)	0.1976 (2)	0.0535 (8)
C18	−0.1801 (4)	0.3598 (4)	0.2497 (2)	0.0566 (8)
C19	−0.0298 (3)	0.3480 (3)	0.36088 (15)	0.0343 (6)
C20	0.1362 (3)	0.3419 (3)	0.30983 (15)	0.0326 (6)
C21	0.3135 (3)	0.3277 (3)	0.33788 (15)	0.0364 (6)
C22	0.0454 (3)	0.2411 (3)	0.48922 (16)	0.0356 (6)
C23	−0.1862 (4)	0.3574 (3)	0.33159 (19)	0.0448 (7)
H4	0.805 (4)	−0.086 (4)	0.0210 (19)	0.067 (9)*
H7A	0.4109	−0.1950	0.2135	0.127*
H7B	0.4435	−0.3567	0.1598	0.127*
H7C	0.3047	−0.1786	0.1418	0.127*
H8	−0.286 (4)	0.364 (4)	0.2286 (18)	0.069 (9)*
H8A	0.6992	0.4405	−0.0333	0.110*
H8B	0.9147	0.3983	−0.0446	0.110*
H8C	0.7907	0.4401	0.0418	0.110*
H9	−0.015 (4)	0.359 (3)	0.1415 (17)	0.051 (8)*
H10	−0.293 (4)	0.359 (3)	0.3689 (16)	0.046 (8)*
H11	0.298 (4)	−0.058 (4)	0.6181 (16)	0.050 (8)*
H14A	0.3184	−0.2075	0.3731	0.094*
H14B	0.5321	−0.2888	0.3728	0.094*
H14C	0.4444	−0.0923	0.3594	0.094*
H15A	0.0950	0.0097	0.7527	0.117*
H15B	0.0711	0.1715	0.8045	0.117*
H15C	0.2530	0.0908	0.7402	0.117*
H100	0.194 (6)	0.528 (6)	0.402 (2)	0.115 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0521 (12)	0.0422 (11)	0.0435 (11)	−0.0152 (9)	0.0075 (9)	0.0009 (9)
O2	0.0800 (16)	0.0445 (12)	0.0836 (17)	−0.0157 (11)	−0.0063 (14)	−0.0039 (11)
O3	0.0437 (12)	0.0780 (16)	0.0813 (16)	−0.0083 (11)	0.0091 (11)	0.0226 (13)
O4	0.0516 (12)	0.0384 (11)	0.0688 (15)	0.0024 (9)	−0.0033 (11)	0.0005 (10)
O5	0.0703 (14)	0.0553 (12)	0.0413 (12)	−0.0083 (10)	−0.0111 (10)	0.0038 (10)
O6	0.0384 (11)	0.0491 (12)	0.0632 (14)	−0.0083 (9)	−0.0136 (10)	−0.0153 (10)
O7	0.0265 (10)	0.0509 (11)	0.0612 (13)	−0.0027 (9)	−0.0026 (9)	−0.0088 (9)
O10	0.0368 (10)	0.0392 (10)	0.0383 (11)	−0.0022 (8)	−0.0004 (8)	0.0034 (8)
N1	0.0488 (14)	0.0449 (14)	0.0428 (14)	−0.0146 (11)	−0.0063 (11)	−0.0024 (11)
N2	0.0396 (13)	0.0523 (14)	0.0423 (13)	−0.0134 (11)	−0.0064 (11)	0.0080 (11)
N3	0.0323 (12)	0.0326 (11)	0.0472 (13)	−0.0094 (9)	−0.0020 (10)	0.0015 (10)
N4	0.0381 (12)	0.0353 (11)	0.0379 (13)	−0.0111 (9)	−0.0032 (10)	0.0030 (9)
C1	0.0447 (16)	0.0452 (16)	0.0340 (15)	−0.0119 (13)	−0.0097 (12)	0.0031 (12)
C3	0.0554 (19)	0.0443 (17)	0.0540 (19)	−0.0106 (14)	−0.0174 (16)	0.0008 (14)
C4	0.0474 (19)	0.056 (2)	0.064 (2)	0.0004 (16)	−0.0003 (17)	−0.0003 (17)
C5	0.0386 (16)	0.062 (2)	0.0477 (18)	−0.0082 (14)	−0.0073 (14)	0.0099 (15)
C7	0.109 (3)	0.059 (2)	0.096 (3)	−0.043 (2)	−0.016 (3)	0.003 (2)
C8	0.058 (2)	0.084 (3)	0.076 (2)	−0.0272 (19)	−0.0073 (18)	0.029 (2)
C12	0.0408 (15)	0.0413 (15)	0.0433 (17)	−0.0172 (12)	−0.0063 (13)	0.0049 (12)
C19	0.0319 (14)	0.0267 (12)	0.0407 (15)	−0.0065 (10)	−0.0047 (11)	0.0032 (11)
C16	0.0406 (15)	0.0349 (14)	0.0417 (16)	−0.0109 (11)	−0.0035 (13)	0.0049 (11)
C10	0.0322 (14)	0.0323 (14)	0.0593 (19)	−0.0109 (11)	−0.0036 (13)	0.0039 (13)
C11	0.0434 (16)	0.0387 (15)	0.0505 (19)	−0.0117 (12)	−0.0151 (14)	0.0139 (13)
C14	0.057 (2)	0.0458 (17)	0.072 (2)	−0.0094 (15)	0.0066 (17)	−0.0172 (15)
C15	0.086 (3)	0.087 (3)	0.049 (2)	−0.011 (2)	−0.0185 (18)	0.0160 (18)
C17	0.057 (2)	0.064 (2)	0.0436 (18)	−0.0206 (15)	−0.0203 (16)	0.0095 (15)
C18	0.0455 (18)	0.065 (2)	0.070 (2)	−0.0221 (15)	−0.0291 (17)	0.0087 (16)
C20	0.0305 (13)	0.0270 (12)	0.0381 (15)	−0.0068 (10)	−0.0068 (11)	0.0018 (10)
C21	0.0313 (14)	0.0370 (14)	0.0402 (15)	−0.0117 (11)	−0.0049 (12)	0.0013 (12)
C22	0.0296 (13)	0.0334 (13)	0.0440 (17)	−0.0128 (11)	−0.0046 (11)	0.0063 (11)
C23	0.0325 (15)	0.0410 (15)	0.062 (2)	−0.0140 (12)	−0.0100 (15)	0.0078 (14)

Geometric parameters (Å, º) top

O10—C22	1.357 (3)	C19—C23	1.376 (4)
O10—C19	1.394 (3)	C16—C17	1.375 (4)
O6—C21	1.312 (3)	C10—C11	1.382 (4)
O6—H100	0.92 (4)	C12—C11	1.370 (4)
O1—C1	1.353 (3)	C5—C4	1.379 (4)
O1—C16	1.403 (3)	C18—C17	1.374 (4)
O7—C21	1.206 (3)	C18—C23	1.374 (4)
O2—C3	1.349 (3)	C18—H8	0.95 (3)
O2—C7	1.427 (4)	C4—C3	1.370 (4)
O3—C5	1.344 (3)	C4—H4	0.93 (3)
O3—C8	1.435 (4)	C17—H9	0.94 (3)
O4—C10	1.337 (3)	C14—H14A	0.9600
O4—C14	1.438 (4)	C14—H14B	0.9600
N4—C22	1.317 (3)	C14—H14C	0.9600
N4—C12	1.345 (3)	C11—H11	0.93 (3)
N1—C1	1.319 (3)	C8—H8A	0.9600
N1—C3	1.334 (3)	C8—H8B	0.9600
N3—C22	1.322 (3)	C8—H8C	0.9600
N3—C10	1.331 (3)	C15—H15A	0.9600
N2—C1	1.323 (3)	C15—H15B	0.9600
N2—C5	1.327 (3)	C15—H15C	0.9600
O5—C12	1.337 (3)	C7—H7A	0.9600
O5—C15	1.432 (3)	C7—H7B	0.9600
C20—C16	1.381 (3)	C7—H7C	0.9600
C20—C19	1.396 (3)	C23—H10	0.94 (3)
C20—C21	1.508 (3)

C22—O10—C19	122.48 (19)	C5—C4—H4	120.6 (19)
C21—O6—H100	113 (3)	N1—C3—O2	118.6 (3)
C1—O1—C16	120.7 (2)	N1—C3—C4	124.0 (3)
C3—O2—C7	117.8 (3)	O2—C3—C4	117.4 (3)
C5—O3—C8	117.6 (2)	C18—C17—C16	119.5 (3)
C10—O4—C14	118.1 (2)	C18—C17—H9	120.6 (17)
C22—N4—C12	115.4 (2)	C16—C17—H9	119.8 (17)
C1—N1—C3	113.4 (2)	O4—C14—H14A	109.5
C22—N3—C10	113.4 (2)	O4—C14—H14B	109.5
C1—N2—C5	114.1 (2)	H14A—C14—H14B	109.5
C12—O5—C15	118.7 (2)	O4—C14—H14C	109.5
C16—C20—C19	116.5 (2)	H14A—C14—H14C	109.5
C16—C20—C21	118.9 (2)	H14B—C14—H14C	109.5
C19—C20—C21	124.6 (2)	C12—C11—C10	115.6 (2)
N1—C1—N2	129.6 (3)	C12—C11—H11	123.1 (17)
N1—C1—O1	119.1 (2)	C10—C11—H11	121.2 (17)
N2—C1—O1	111.3 (2)	O3—C8—H8A	109.5
C23—C19—O10	115.5 (2)	O3—C8—H8B	109.5
C23—C19—C20	122.0 (2)	H8A—C8—H8B	109.5
O10—C19—C20	122.2 (2)	O3—C8—H8C	109.5
C17—C16—C20	122.4 (3)	H8A—C8—H8C	109.5
C17—C16—O1	118.7 (2)	H8B—C8—H8C	109.5
C20—C16—O1	118.1 (2)	O5—C15—H15A	109.5
N3—C10—O4	118.6 (3)	O5—C15—H15B	109.5
N3—C10—C11	124.5 (2)	H15A—C15—H15B	109.5
O4—C10—C11	117.0 (2)	O5—C15—H15C	109.5
O7—C21—O6	121.1 (2)	H15A—C15—H15C	109.5
O7—C21—C20	121.3 (2)	H15B—C15—H15C	109.5
O6—C21—C20	117.6 (2)	O2—C7—H7A	109.5
O5—C12—N4	111.6 (2)	O2—C7—H7B	109.5
O5—C12—C11	126.3 (2)	H7A—C7—H7B	109.5
N4—C12—C11	122.1 (3)	O2—C7—H7C	109.5
N2—C5—O3	118.4 (3)	H7A—C7—H7C	109.5
N2—C5—C4	123.2 (3)	H7B—C7—H7C	109.5
O3—C5—C4	118.4 (3)	N4—C22—N3	129.0 (2)
C17—C18—C23	120.1 (3)	N4—C22—O10	111.6 (2)
C17—C18—H8	119.5 (19)	N3—C22—O10	119.4 (2)
C23—C18—H8	120.4 (19)	C18—C23—C19	119.5 (3)
C3—C4—C5	115.6 (3)	C18—C23—H10	122.5 (16)
C3—C4—H4	123.7 (19)	C19—C23—H10	118.0 (16)

C3—N1—C1—N2	2.0 (4)	C22—N4—C12—C11	0.2 (4)
C3—N1—C1—O1	−179.1 (2)	C1—N2—C5—O3	178.9 (2)
C5—N2—C1—N1	−0.9 (4)	C1—N2—C5—C4	−0.7 (4)
C5—N2—C1—O1	−179.9 (2)	C8—O3—C5—N2	−6.4 (4)
C16—O1—C1—N1	1.7 (3)	C8—O3—C5—C4	173.2 (3)
C16—O1—C1—N2	−179.2 (2)	N2—C5—C4—C3	1.1 (5)
C22—O10—C19—C23	121.8 (2)	O3—C5—C4—C3	−178.5 (3)
C22—O10—C19—C20	−65.0 (3)	C1—N1—C3—O2	178.5 (2)
C16—C20—C19—C23	0.7 (3)	C1—N1—C3—C4	−1.5 (4)
C21—C20—C19—C23	−178.6 (2)	C7—O2—C3—N1	−2.0 (4)
C16—C20—C19—O10	−172.1 (2)	C7—O2—C3—C4	177.9 (3)
C21—C20—C19—O10	8.6 (3)	C5—C4—C3—N1	0.1 (5)
C19—C20—C16—C17	−1.1 (4)	C5—C4—C3—O2	−179.8 (3)
C21—C20—C16—C17	178.3 (2)	C23—C18—C17—C16	0.9 (5)
C19—C20—C16—O1	168.2 (2)	C20—C16—C17—C18	0.3 (4)
C21—C20—C16—O1	−12.4 (3)	O1—C16—C17—C18	−169.0 (3)
C1—O1—C16—C17	−91.0 (3)	O5—C12—C11—C10	178.6 (3)
C1—O1—C16—C20	99.3 (3)	N4—C12—C11—C10	−1.1 (4)
C22—N3—C10—O4	−179.5 (2)	N3—C10—C11—C12	0.5 (4)
C22—N3—C10—C11	1.0 (4)	O4—C10—C11—C12	−179.1 (2)
C14—O4—C10—N3	0.0 (4)	C12—N4—C22—N3	1.6 (4)
C14—O4—C10—C11	179.6 (3)	C12—N4—C22—O10	−178.98 (19)
C16—C20—C21—O7	−50.1 (3)	C10—N3—C22—N4	−2.1 (4)
C19—C20—C21—O7	129.3 (3)	C10—N3—C22—O10	178.5 (2)
C16—C20—C21—O6	129.1 (3)	C19—O10—C22—N4	179.9 (2)
C19—C20—C21—O6	−51.6 (3)	C19—O10—C22—N3	−0.6 (3)
C15—O5—C12—N4	178.7 (3)	C17—C18—C23—C19	−1.2 (4)
C15—O5—C12—C11	−1.1 (4)	O10—C19—C23—C18	173.6 (2)
C22—N4—C12—O5	−179.6 (2)	C20—C19—C23—C18	0.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O7ⁱ	0.93 (3)	2.43 (3)	3.332 (3)	164 (2)
O6—H100···N4ⁱⁱ	0.92 (4)	1.77 (4)	2.675 (2)	168 (4)

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈N₄O₈
M_r	430.37
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	7.7779 (12), 8.2973 (13), 16.883 (3)
α, β, γ (°)	87.899 (3), 79.054 (3), 70.276 (3)
V (Å³)	1006.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.40 × 0.30 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.947, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8103, 4089, 2777
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.158, 1.14
No. of reflections	4089
No. of parameters	308
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare, 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin, 1993), PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

O10—C22	1.357 (3)	O1—C1	1.353 (3)
O10—C19	1.394 (3)	O1—C16	1.403 (3)
O6—C21	1.312 (3)	O7—C21	1.206 (3)

C16—O1—C1—N1	1.7 (3)	C15—O5—C12—N4	178.7 (3)
C22—O10—C19—C23	121.8 (2)	C8—O3—C5—N2	−6.4 (4)
C1—O1—C16—C17	−91.0 (3)	C7—O2—C3—N1	−2.0 (4)
C14—O4—C10—N3	0.0 (4)	C19—O10—C22—N3	−0.6 (3)
C19—C20—C21—O7	129.3 (3)