Ethyl {6-[6-(ethoxy­carbon­yl)picolin­amido­carbon­yl]picolinamido­carbon­yl}picolinate

Li, X.; Wang, Y.; Zhan, C.; Yao, J.

doi:10.1107/S1600536808040932

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o51

doi:10.1107/S1600536808040932

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Ethyl {6-[6-(ethoxycarbonyl)picolinamidocarbonyl]picolinamidocarbonyl}picolinate

Xiao Li,^a Yaobing Wang,^a Chuanlang Zhan ^a and Jiannian Yao ^a ^*

^aBeijing National Laboratory for Molecular Sciences (BNLMS), Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China, and Graduate University of the Chinese Academy of Sciences (GUCAS), Beijing 100049, People's Republic of China
^*Correspondence e-mail: jnyao@iccas.ac.cn

(Received 24 November 2008; accepted 4 December 2008; online 10 December 2008)

The title molecule, C₂₅H₂₁N₅O₈, adopts a helical conformation, which is stabilized by two intramolecular bifurcated N—H⋯(N,N) hydrogen bonds.

Related literature

For a review on aromatic oligoamides (AOAs), see, for example: Huc (2004 ). For related compounds, see: Li et al. (2008 ).

Experimental

Crystal data

C₂₅H₂₁N₅O₈
M_r = 519.47
Monoclinic, P 2₁ /c
a = 7.4952 (8) Å
b = 19.998 (2) Å
c = 15.9966 (17) Å
β = 96.376 (1)°
V = 2382.8 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 (2) K
0.32 × 0.22 × 0.18 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999 ) T_min = 0.966, T_max = 0.980
30537 measured reflections
6101 independent reflections
5457 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.08
6101 reflections
354 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N3	0.885 (14)	2.153 (14)	2.6131 (13)	111.7 (11)
N4—H4⋯N5	0.885 (14)	2.158 (14)	2.6297 (12)	112.8 (11)
N2—H2⋯N3	0.878 (15)	2.148 (14)	2.6006 (12)	111.4 (11)
N2—H2⋯N1	0.878 (15)	2.151 (14)	2.6329 (12)	114.0 (11)

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 1999).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808040932/hb2864sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040932/hb2864Isup2.hkl

checkCIF report

Comment top

The stucture of the title compound is shown in Fig. 1. Dimensions are available in the archived CIF. The hydrogen bonds are listed in Table 1. For background, see for example: Huc (2004). For related compounds, see: Li et al. (2008).

Related literature top

For a review on aromatic oligoamides (AOAs), see, for example: Huc (2004). For related compounds, see: Li et al. (2008).

Experimental top

The title compound was obtained from 2-ethoxycarbonyl- 6-pyridinoyl amide and 2,6-pyridinoyl dichloride and recrystallised from DMF/ethyl ether to yield colourless prisms of (I).

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear (Rigaku, 1999); data reduction: CrystalClear (Rigaku, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: CrystalStructure (Rigaku, 1999).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids for the non-hydrogen atoms. The hydrogen bonds are shown as double-dashed lines.
	Fig. 2. The formation of the title compound.

Ethyl {6-[6-(ethoxycarbonyl)picolinamidocarbonyl]picolinamidocarbonyl}picolinate top

Crystal data top

C₂₅H₂₁N₅O₈	F(000) = 1080
M_r = 519.47	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 6439 reflections
a = 7.4952 (8) Å	θ = 2.6–26.0°
b = 19.998 (2) Å	µ = 0.11 mm⁻¹
c = 15.9966 (17) Å	T = 113 K
β = 96.376 (1)°	Prism, colorless
V = 2382.8 (4) Å³	0.32 × 0.22 × 0.18 mm
Z = 4

Data collection top

Rigaku Saturn diffractometer	6101 independent reflections
Radiation source: rotating anode	5457 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.025
Detector resolution: 7.31 pixels mm^-1	θ_max = 28.7°, θ_min = 2.4°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999)	k = −27→24
T_min = 0.966, T_max = 0.980	l = −21→21
30537 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0481P)² + 0.4996P] where P = (F_o² + 2F_c²)/3
6101 reflections	(Δ/σ)_max = 0.001
354 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₅H₂₁N₅O₈	V = 2382.8 (4) Å³
M_r = 519.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4952 (8) Å	µ = 0.11 mm⁻¹
b = 19.998 (2) Å	T = 113 K
c = 15.9966 (17) Å	0.32 × 0.22 × 0.18 mm
β = 96.376 (1)°

Data collection top

Rigaku Saturn diffractometer	6101 independent reflections
Absorption correction: multi-scan (CrystalcClear; Rigaku, 1999)	5457 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.980	R_int = 0.025
30537 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.32 e Å⁻³
6101 reflections	Δρ_min = −0.17 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 > 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	−0.13320 (11)	0.87694 (4)	0.72665 (5)	0.02977 (17)
O2	0.06124 (11)	0.85871 (4)	0.63149 (5)	0.02910 (17)
O3	−0.16781 (12)	0.59423 (4)	0.88294 (6)	0.0395 (2)
O4	−0.33384 (11)	0.65393 (4)	1.02334 (5)	0.03521 (19)
O5	−0.24510 (13)	0.99672 (4)	0.94666 (5)	0.0397 (2)
O6	0.08420 (13)	1.00415 (4)	0.86648 (5)	0.0391 (2)
O7	0.21781 (10)	0.70449 (4)	0.93765 (4)	0.02615 (16)
O8	0.37042 (9)	0.67410 (4)	0.82982 (4)	0.02587 (16)
N1	−0.10247 (10)	0.74283 (4)	0.76977 (5)	0.02135 (16)
N2	−0.21026 (12)	0.70511 (4)	0.91366 (5)	0.02446 (18)
N3	−0.25843 (11)	0.82284 (4)	0.97648 (5)	0.02253 (17)
N4	−0.04508 (12)	0.91296 (4)	0.92339 (5)	0.02641 (18)
N5	0.20551 (11)	0.83332 (4)	0.87730 (5)	0.02099 (16)
C1	−0.04508 (13)	0.83975 (5)	0.68831 (6)	0.02336 (19)
C2	−0.03851 (12)	0.76501 (5)	0.70001 (6)	0.02167 (19)
C3	0.02896 (13)	0.72245 (5)	0.64172 (6)	0.0245 (2)
H3	0.0764	0.7400	0.5936	0.029*
C4	0.02507 (13)	0.65399 (5)	0.65576 (6)	0.0264 (2)
H4A	0.0657	0.6237	0.6162	0.032*
C5	−0.03894 (13)	0.63047 (5)	0.72829 (7)	0.0262 (2)
H5	−0.0419	0.5839	0.7398	0.031*
C6	−0.09874 (12)	0.67674 (5)	0.78370 (6)	0.02280 (19)
C7	−0.16141 (13)	0.65290 (5)	0.86502 (7)	0.0260 (2)
C8	−0.29462 (13)	0.70359 (5)	0.98611 (6)	0.0248 (2)
C9	−0.34013 (13)	0.77315 (5)	1.01301 (6)	0.0241 (2)
C10	−0.46393 (14)	0.78407 (7)	1.07012 (7)	0.0334 (2)
H10	−0.5180	0.7478	1.0961	0.040*
C11	−0.50571 (15)	0.84953 (7)	1.08782 (8)	0.0400 (3)
H11	−0.5904	0.8588	1.1263	0.048*
C12	−0.42408 (15)	0.90164 (6)	1.04950 (7)	0.0353 (3)
H12	−0.4530	0.9468	1.0603	0.042*
C13	−0.29831 (14)	0.88586 (5)	0.99470 (6)	0.0263 (2)
C14	−0.19693 (15)	0.93888 (5)	0.95273 (6)	0.0287 (2)
C15	0.08115 (15)	0.94475 (5)	0.88163 (6)	0.0272 (2)
C16	0.22015 (13)	0.89727 (5)	0.85479 (6)	0.0240 (2)
C17	0.35075 (15)	0.92050 (6)	0.80694 (7)	0.0318 (2)
H17	0.3587	0.9667	0.7939	0.038*
C18	0.46885 (15)	0.87489 (6)	0.77877 (8)	0.0350 (3)
H18	0.5603	0.8892	0.7462	0.042*
C19	0.45178 (14)	0.80778 (6)	0.79891 (7)	0.0290 (2)
H19	0.5286	0.7751	0.7788	0.035*
C20	0.31961 (12)	0.78940 (5)	0.84913 (6)	0.02153 (19)
C21	0.29545 (12)	0.71868 (5)	0.87815 (6)	0.02146 (19)
C22	0.06263 (18)	0.92999 (5)	0.61175 (7)	0.0342 (2)
H22A	0.0827	0.9568	0.6640	0.041*
H22B	−0.0532	0.9435	0.5806	0.041*
C23	0.2126 (2)	0.94046 (6)	0.55884 (9)	0.0482 (4)
H23A	0.3267	0.9282	0.5912	0.072*
H23B	0.2163	0.9876	0.5423	0.072*
H23C	0.1931	0.9124	0.5084	0.072*
C24	0.35652 (15)	0.60428 (5)	0.85650 (7)	0.0275 (2)
H24A	0.2315	0.5941	0.8666	0.033*
H24B	0.4356	0.5965	0.9094	0.033*
C25	0.41238 (17)	0.56010 (6)	0.78771 (7)	0.0352 (2)
H25A	0.3290	0.5662	0.7366	0.053*
H25B	0.4104	0.5133	0.8056	0.053*
H25C	0.5341	0.5721	0.7762	0.053*
H4	−0.0313 (18)	0.8692 (7)	0.9284 (8)	0.036 (4)*
H2	−0.1908 (19)	0.7449 (8)	0.8932 (9)	0.040 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0356 (4)	0.0277 (4)	0.0269 (4)	0.0077 (3)	0.0077 (3)	−0.0011 (3)
O2	0.0378 (4)	0.0242 (4)	0.0268 (4)	0.0026 (3)	0.0104 (3)	0.0007 (3)
O3	0.0507 (5)	0.0201 (4)	0.0503 (5)	−0.0036 (3)	0.0176 (4)	0.0003 (3)
O4	0.0350 (4)	0.0360 (4)	0.0355 (4)	−0.0062 (3)	0.0075 (3)	0.0099 (3)
O5	0.0549 (5)	0.0247 (4)	0.0386 (5)	0.0185 (4)	0.0005 (4)	−0.0020 (3)
O6	0.0650 (6)	0.0165 (4)	0.0358 (4)	−0.0003 (4)	0.0059 (4)	0.0058 (3)
O7	0.0308 (4)	0.0222 (4)	0.0266 (4)	0.0031 (3)	0.0085 (3)	0.0035 (3)
O8	0.0267 (4)	0.0239 (4)	0.0280 (4)	0.0045 (3)	0.0076 (3)	0.0009 (3)
N1	0.0193 (4)	0.0215 (4)	0.0231 (4)	−0.0004 (3)	0.0013 (3)	−0.0035 (3)
N2	0.0272 (4)	0.0203 (4)	0.0269 (4)	−0.0018 (3)	0.0075 (3)	0.0004 (3)
N3	0.0231 (4)	0.0256 (4)	0.0186 (4)	0.0055 (3)	0.0007 (3)	−0.0008 (3)
N4	0.0374 (5)	0.0147 (4)	0.0277 (4)	0.0050 (3)	0.0059 (3)	0.0009 (3)
N5	0.0218 (4)	0.0188 (4)	0.0218 (4)	−0.0021 (3)	−0.0004 (3)	0.0022 (3)
C1	0.0249 (5)	0.0267 (5)	0.0179 (4)	0.0022 (4)	0.0001 (3)	−0.0014 (3)
C2	0.0187 (4)	0.0245 (5)	0.0211 (4)	0.0011 (3)	−0.0011 (3)	−0.0036 (3)
C3	0.0209 (4)	0.0301 (5)	0.0218 (4)	0.0016 (4)	0.0001 (3)	−0.0058 (4)
C4	0.0223 (4)	0.0286 (5)	0.0278 (5)	0.0021 (4)	−0.0002 (4)	−0.0109 (4)
C5	0.0234 (5)	0.0220 (5)	0.0325 (5)	−0.0012 (4)	0.0005 (4)	−0.0084 (4)
C6	0.0194 (4)	0.0218 (5)	0.0269 (5)	−0.0022 (3)	0.0013 (3)	−0.0053 (4)
C7	0.0241 (5)	0.0208 (5)	0.0334 (5)	−0.0028 (4)	0.0052 (4)	−0.0024 (4)
C8	0.0197 (4)	0.0309 (5)	0.0239 (5)	−0.0021 (4)	0.0020 (3)	0.0026 (4)
C9	0.0190 (4)	0.0340 (5)	0.0189 (4)	0.0008 (4)	0.0009 (3)	−0.0006 (4)
C10	0.0233 (5)	0.0522 (7)	0.0254 (5)	−0.0044 (5)	0.0061 (4)	−0.0067 (5)
C11	0.0255 (5)	0.0603 (8)	0.0357 (6)	0.0018 (5)	0.0099 (4)	−0.0177 (6)
C12	0.0280 (5)	0.0441 (7)	0.0332 (6)	0.0112 (5)	0.0014 (4)	−0.0141 (5)
C13	0.0260 (5)	0.0299 (5)	0.0218 (4)	0.0099 (4)	−0.0017 (4)	−0.0048 (4)
C14	0.0375 (6)	0.0245 (5)	0.0231 (5)	0.0103 (4)	−0.0013 (4)	−0.0029 (4)
C15	0.0412 (6)	0.0179 (4)	0.0219 (4)	−0.0010 (4)	0.0004 (4)	0.0022 (3)
C16	0.0281 (5)	0.0200 (5)	0.0230 (4)	−0.0040 (4)	−0.0017 (4)	0.0036 (3)
C17	0.0330 (5)	0.0279 (5)	0.0338 (5)	−0.0085 (4)	0.0005 (4)	0.0108 (4)
C18	0.0250 (5)	0.0423 (7)	0.0383 (6)	−0.0051 (4)	0.0060 (4)	0.0166 (5)
C19	0.0203 (4)	0.0365 (6)	0.0304 (5)	0.0028 (4)	0.0040 (4)	0.0096 (4)
C20	0.0183 (4)	0.0236 (5)	0.0220 (4)	0.0000 (3)	−0.0007 (3)	0.0037 (3)
C21	0.0180 (4)	0.0229 (5)	0.0229 (4)	0.0024 (3)	0.0001 (3)	0.0015 (3)
C22	0.0510 (7)	0.0238 (5)	0.0287 (5)	0.0041 (5)	0.0082 (5)	0.0031 (4)
C23	0.0808 (10)	0.0273 (6)	0.0419 (7)	−0.0084 (6)	0.0309 (7)	−0.0045 (5)
C24	0.0320 (5)	0.0221 (5)	0.0288 (5)	0.0063 (4)	0.0056 (4)	0.0017 (4)
C25	0.0420 (6)	0.0298 (6)	0.0350 (6)	0.0093 (5)	0.0095 (5)	−0.0033 (4)

Geometric parameters (Å, º) top

O1—C1	1.2064 (12)	C8—C9	1.5063 (15)
O2—C1	1.3289 (12)	C9—C10	1.3898 (14)
O2—C22	1.4603 (13)	C10—C11	1.3825 (18)
O3—C7	1.2100 (13)	C10—H10	0.9500
O4—C8	1.2109 (13)	C11—C12	1.3854 (19)
O5—C14	1.2123 (13)	C11—H11	0.9500
O6—C15	1.2131 (13)	C12—C13	1.3930 (15)
O7—C21	1.2034 (12)	C12—H12	0.9500
O8—C21	1.3434 (12)	C13—C14	1.5052 (16)
O8—C24	1.4671 (12)	C15—C16	1.5068 (15)
N1—C2	1.3382 (13)	C16—C17	1.3880 (15)
N1—C6	1.3401 (13)	C17—C18	1.3809 (17)
N2—C7	1.3760 (13)	C17—H17	0.9500
N2—C8	1.3809 (13)	C18—C19	1.3893 (16)
N2—H2	0.878 (15)	C18—H18	0.9500
N3—C13	1.3348 (13)	C19—C20	1.3924 (14)
N3—C9	1.3354 (13)	C19—H19	0.9500
N4—C15	1.3732 (14)	C20—C21	1.5057 (13)
N4—C14	1.3796 (14)	C22—C23	1.4949 (18)
N4—H4	0.885 (14)	C22—H22A	0.9900
N5—C16	1.3364 (12)	C22—H22B	0.9900
N5—C20	1.3384 (13)	C23—H23A	0.9800
C1—C2	1.5064 (14)	C23—H23B	0.9800
C2—C3	1.3979 (13)	C23—H23C	0.9800
C3—C4	1.3882 (15)	C24—C25	1.5064 (14)
C3—H3	0.9500	C24—H24A	0.9900
C4—C5	1.3859 (15)	C24—H24B	0.9900
C4—H4A	0.9500	C25—H25A	0.9800
C5—C6	1.3895 (14)	C25—H25B	0.9800
C5—H5	0.9500	C25—H25C	0.9800
C6—C7	1.5086 (14)

C1—O2—C22	116.47 (8)	C12—C13—C14	122.10 (10)
C21—O8—C24	114.60 (8)	O5—C14—N4	125.50 (11)
C2—N1—C6	117.56 (8)	O5—C14—C13	123.18 (10)
C7—N2—C8	129.30 (9)	N4—C14—C13	111.32 (8)
C7—N2—H2	114.2 (9)	O6—C15—N4	125.43 (11)
C8—N2—H2	116.3 (9)	O6—C15—C16	122.08 (10)
C13—N3—C9	118.83 (9)	N4—C15—C16	112.49 (8)
C15—N4—C14	129.10 (9)	N5—C16—C17	123.57 (10)
C15—N4—H4	115.0 (9)	N5—C16—C15	116.50 (9)
C14—N4—H4	115.7 (9)	C17—C16—C15	119.90 (9)
C16—N5—C20	117.56 (9)	C18—C17—C16	118.41 (10)
O1—C1—O2	125.14 (10)	C18—C17—H17	120.8
O1—C1—C2	124.11 (9)	C16—C17—H17	120.8
O2—C1—C2	110.75 (8)	C17—C18—C19	118.91 (10)
N1—C2—C3	122.96 (9)	C17—C18—H18	120.5
N1—C2—C1	114.99 (8)	C19—C18—H18	120.5
C3—C2—C1	122.04 (9)	C18—C19—C20	118.59 (10)
C4—C3—C2	118.48 (10)	C18—C19—H19	120.7
C4—C3—H3	120.8	C20—C19—H19	120.7
C2—C3—H3	120.8	N5—C20—C19	122.90 (9)
C5—C4—C3	119.04 (9)	N5—C20—C21	114.16 (8)
C5—C4—H4A	120.5	C19—C20—C21	122.92 (9)
C3—C4—H4A	120.5	O7—C21—O8	124.66 (9)
C4—C5—C6	118.31 (10)	O7—C21—C20	123.41 (9)
C4—C5—H5	120.8	O8—C21—C20	111.94 (8)
C6—C5—H5	120.8	O2—C22—C23	106.44 (9)
N1—C6—C5	123.57 (9)	O2—C22—H22A	110.4
N1—C6—C7	116.89 (8)	C23—C22—H22A	110.4
C5—C6—C7	119.53 (9)	O2—C22—H22B	110.4
O3—C7—N2	125.58 (10)	C23—C22—H22B	110.4
O3—C7—C6	122.35 (9)	H22A—C22—H22B	108.6
N2—C7—C6	112.06 (8)	C22—C23—H23A	109.5
O4—C8—N2	126.13 (10)	C22—C23—H23B	109.5
O4—C8—C9	122.81 (9)	H23A—C23—H23B	109.5
N2—C8—C9	111.02 (8)	C22—C23—H23C	109.5
N3—C9—C10	122.87 (10)	H23A—C23—H23C	109.5
N3—C9—C8	115.64 (8)	H23B—C23—H23C	109.5
C10—C9—C8	121.45 (10)	O8—C24—C25	108.13 (8)
C11—C10—C9	117.80 (11)	O8—C24—H24A	110.1
C11—C10—H10	121.1	C25—C24—H24A	110.1
C9—C10—H10	121.1	O8—C24—H24B	110.1
C10—C11—C12	120.02 (10)	C25—C24—H24B	110.1
C10—C11—H11	120.0	H24A—C24—H24B	108.4
C12—C11—H11	120.0	C24—C25—H25A	109.5
C11—C12—C13	118.10 (11)	C24—C25—H25B	109.5
C11—C12—H12	121.0	H25A—C25—H25B	109.5
C13—C12—H12	121.0	C24—C25—H25C	109.5
N3—C13—C12	122.34 (11)	H25A—C25—H25C	109.5
N3—C13—C14	115.55 (9)	H25B—C25—H25C	109.5

C22—O2—C1—O1	−3.25 (15)	C9—N3—C13—C12	−0.98 (14)
C22—O2—C1—C2	177.85 (8)	C9—N3—C13—C14	178.44 (8)
C6—N1—C2—C3	0.73 (13)	C11—C12—C13—N3	1.89 (16)
C6—N1—C2—C1	−179.54 (8)	C11—C12—C13—C14	−177.48 (10)
O1—C1—C2—N1	−15.36 (14)	C15—N4—C14—O5	−0.58 (18)
O2—C1—C2—N1	163.55 (8)	C15—N4—C14—C13	179.72 (9)
O1—C1—C2—C3	164.37 (10)	N3—C13—C14—O5	162.22 (10)
O2—C1—C2—C3	−16.71 (12)	C12—C13—C14—O5	−18.36 (16)
N1—C2—C3—C4	1.73 (14)	N3—C13—C14—N4	−18.07 (12)
C1—C2—C3—C4	−177.98 (8)	C12—C13—C14—N4	161.35 (9)
C2—C3—C4—C5	−2.40 (14)	C14—N4—C15—O6	3.77 (18)
C3—C4—C5—C6	0.72 (14)	C14—N4—C15—C16	−175.83 (9)
C2—N1—C6—C5	−2.58 (14)	C20—N5—C16—C17	−2.57 (14)
C2—N1—C6—C7	176.59 (8)	C20—N5—C16—C15	175.38 (8)
C4—C5—C6—N1	1.87 (15)	O6—C15—C16—N5	178.10 (10)
C4—C5—C6—C7	−177.27 (9)	N4—C15—C16—N5	−2.29 (12)
C8—N2—C7—O3	−8.40 (18)	O6—C15—C16—C17	−3.88 (15)
C8—N2—C7—C6	170.93 (9)	N4—C15—C16—C17	175.74 (9)
N1—C6—C7—O3	178.12 (10)	N5—C16—C17—C18	2.05 (16)
C5—C6—C7—O3	−2.68 (15)	C15—C16—C17—C18	−175.83 (10)
N1—C6—C7—N2	−1.24 (12)	C16—C17—C18—C19	0.37 (16)
C5—C6—C7—N2	177.96 (9)	C17—C18—C19—C20	−2.07 (16)
C7—N2—C8—O4	4.13 (18)	C16—N5—C20—C19	0.70 (14)
C7—N2—C8—C9	−173.76 (9)	C16—N5—C20—C21	179.34 (8)
C13—N3—C9—C10	−0.73 (14)	C18—C19—C20—N5	1.58 (15)
C13—N3—C9—C8	177.19 (8)	C18—C19—C20—C21	−176.94 (9)
O4—C8—C9—N3	167.30 (9)	C24—O8—C21—O7	−1.92 (13)
N2—C8—C9—N3	−14.72 (12)	C24—O8—C21—C20	178.12 (8)
O4—C8—C9—C10	−14.75 (15)	N5—C20—C21—O7	−19.00 (13)
N2—C8—C9—C10	163.23 (9)	C19—C20—C21—O7	159.64 (10)
N3—C9—C10—C11	1.43 (15)	N5—C20—C21—O8	160.96 (8)
C8—C9—C10—C11	−176.37 (10)	C19—C20—C21—O8	−20.40 (13)
C9—C10—C11—C12	−0.44 (17)	C1—O2—C22—C23	170.48 (10)
C10—C11—C12—C13	−1.12 (17)	C21—O8—C24—C25	168.94 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.885 (14)	2.153 (14)	2.6131 (13)	111.7 (11)
N4—H4···N5	0.885 (14)	2.158 (14)	2.6297 (12)	112.8 (11)
N2—H2···N3	0.878 (15)	2.148 (14)	2.6006 (12)	111.4 (11)
N2—H2···N1	0.878 (15)	2.151 (14)	2.6329 (12)	114.0 (11)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₁N₅O₈
M_r	519.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	113
a, b, c (Å)	7.4952 (8), 19.998 (2), 15.9966 (17)
β (°)	96.376 (1)
V (Å³)	2382.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.22 × 0.18

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalcClear; Rigaku, 1999)
T_min, T_max	0.966, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	30537, 6101, 5457
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.08
No. of reflections	6101
No. of parameters	354
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.17

Computer programs: CrystalClear (Rigaku, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N3	0.885 (14)	2.153 (14)	2.6131 (13)	111.7 (11)
N4—H4···N5	0.885 (14)	2.158 (14)	2.6297 (12)	112.8 (11)
N2—H2···N3	0.878 (15)	2.148 (14)	2.6006 (12)	111.4 (11)
N2—H2···N1	0.878 (15)	2.151 (14)	2.6329 (12)	114.0 (11)

Acknowledgements

We thank the NSFC (Nos. 50221201, 20872145, 20733006), the Chinese Academy of Sciences and the National Research Fund for Fundamental Key Project 973 (2006CB806200, 2007CB936401) for support.

References

Huc, I. (2004). Eur. J. Org. Chem. pp. 17-29. Web of Science CrossRef Google Scholar
Li, X., Zhan, C., Wang, Y. & Yao, J. (2008). Chem. Commun. pp. 2444–2446. Web of Science CrossRef Google Scholar
Rigaku (1999). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 1| January 2009| Page o51

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl {6-[6-(eth­oxy­carbon­yl)picolin­amido­carbon­yl]picolinamido­carbon­yl}picolinate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl {6-[6-(ethoxycarbonyl)picolinamidocarbonyl]picolinamidocarbonyl}picolinate