N2,N2′-Bis[2-(ethoxy­carbonyl­meth­oxy)­benzyl­idene]pyridine-2,6-dicarbohydrazide

Luo, F.; Lan, S.; Cheng, C.; Hu, Z.

doi:10.1107/S160053680706477X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o185

https://doi.org/10.1107/S160053680706477X

Open

access

N²,N^2′-Bis[2-(ethoxycarbonylmethoxy)benzylidene]pyridine-2,6-dicarbohydrazide

Feihua Luo,^a Shemin Lan,^a Cuixia Cheng ^a and Zongqiu Hu ^a ^*

^aDepartment of Chemistry, Central China Normal University, Wuhan, Hubei 430079, People's Republic of China
^*Correspondence e-mail: luofh2005@yahoo.com.cn

(Received 13 November 2007; accepted 30 November 2007; online 6 December 2007)

In the title compound, C₂₉H₂₉N₅O₈, the ester group is disordered over two sites with site-occupancy factors of 0.91/0.09. The crystal structure is stabilized by inter- and intramolecular hydrogen-bond interactions.

Related literature

For related literature, see: Chen et al. (1997 ); Thompson (2002 ); Zhao et al. (2004 ).

Experimental

Crystal data

C₂₉H₂₉N₅O₈
M_r = 575.57
Monoclinic, P 2₁ /n
a = 11.5485 (6) Å
b = 21.6606 (11) Å
c = 12.3596 (9) Å
β = 114.779 (1)°
V = 2807.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 299 (2) K
0.32 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
23685 measured reflections
6101 independent reflections
4136 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.076
wR(F²) = 0.231
S = 1.04
6101 reflections
396 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O5ⁱ	0.86	2.53	3.353 (3)	161
C2—H2⋯O7ⁱⁱ	0.93	2.40	3.304 (4)	165
C17—H17C⋯O2ⁱⁱⁱ	0.96	2.49	2.896 (8)	105
N2—H2A⋯N1	0.86	2.34	2.694 (3)	105
Symmetry codes: (i) -x+2, -y, -z+2; (ii) -x+1, -y, -z+2; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680706477X/bq2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706477X/bq2047Isup2.hkl

checkCIF report

Comment top

The tridentate ligands with 2,6-dipicolinoyhydrazone have been intensively studied due to the interesting coordination mode. (Chen et al., 1997; Thompson, 2002; Zhao et al., 2004). We report here the synthesis and crystal structure of a novel tridentate ligand, the title compound (I) (Fig. 1).

The molecular structure contains one pyridine ring and two substitutional benzene rings. The dihedral angles between the pyridine and benzene planes are 6.50 (13)° for C8—C13 and 26.43 (16)° for C20—C25.

The crystal packing is governed by intermolecular hydrogen bonds interactions. Each molecular can serve as donor and acceptor to form the N–H–O hydrogen bonds with two other neighboring molecules, forming chains parallel to the a axis (Fig. 2; Table 1).

Related literature top

For related literature, see: Chen et al. (1997); Thompson (2002); Zhao et al. (2004).

Experimental top

To a solution of 2-(2-formylphenoxy)acetic acid (1.80 g, 10 mmol) in absolute ethanol (40 ml), a suspension of 2,6-dipicolinoyhydrazine in the same solvent (50 ml) was added at 323 K. The mixture was left to react at reflux for 18 h, then the white needle product was filtered, washed with hot ethanol (20 ml portion) three times and dried in vacuum. Crystals suitable for X-ray diffraction were obtained from acetone-methanol (1:1 v/v) over a period of about three weeks, and unexpecting the carboxyl from the 2-(2-formylphenoxy)acetic acid was esterified in the ethanol solvent.

Structure description top

For related literature, see: Chen et al. (1997); Thompson (2002); Zhao et al. (2004).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
	Fig. 2. A view of the packing of (I). Hydrogen bonds are shown by dashed lines.

N²,N^2'—Bis[2-(ethoxycarbonylmethoxy)benzylidene]pyridine- 2,6-dicarbohydrazide top

Crystal data top

C₂₉H₂₉N₅O₈	Z = 4
M_r = 575.57	F(000) = 1208
Monoclinic, P2₁/n	D_x = 1.362 Mg m⁻³
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.5485 (6) Å	µ = 0.10 mm⁻¹
b = 21.6606 (11) Å	T = 299 K
c = 12.3596 (9) Å	Block, colorless
β = 114.779 (1)°	0.32 × 0.10 × 0.10 mm
V = 2807.1 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4136 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.0°, θ_min = 1.9°
phi and ω scans	h = −14→14
23685 measured reflections	k = −27→27
6101 independent reflections	l = −15→15

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.231	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.1307P)² + 0.5522P] where P = (F_o² + 2F_c²)/3
6101 reflections	(Δ/σ)_max < 0.001
396 parameters	Δρ_max = 0.40 e Å⁻³
12 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₂₉H₂₉N₅O₈	V = 2807.1 (3) Å³
M_r = 575.57	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.5485 (6) Å	µ = 0.10 mm⁻¹
b = 21.6606 (11) Å	T = 299 K
c = 12.3596 (9) Å	0.32 × 0.10 × 0.10 mm
β = 114.779 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4136 reflections with I > 2σ(I)
23685 measured reflections	R_int = 0.032
6101 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.076	12 restraints
wR(F²) = 0.231	H-atom parameters constrained
S = 1.04	Δρ_max = 0.40 e Å⁻³
6101 reflections	Δρ_min = −0.52 e Å⁻³
396 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)
C1	0.4448 (2)	−0.07839 (10)	1.0814 (2)	0.0440 (5)
C2	0.3444 (3)	−0.09691 (12)	1.1079 (2)	0.0539 (6)
H2	0.3247	−0.0755	1.1632	0.065*
C3	0.2749 (3)	−0.14779 (13)	1.0499 (3)	0.0633 (7)
H3	0.2074	−0.1617	1.0658	0.076*
C4	0.3065 (3)	−0.17779 (12)	0.9680 (3)	0.0605 (7)
H4	0.2622	−0.2129	0.9291	0.073*
C5	0.4054 (3)	−0.15491 (11)	0.9445 (2)	0.0506 (6)
C6	0.5243 (2)	−0.02429 (11)	1.1467 (2)	0.0453 (5)
C7	0.8231 (2)	0.02966 (12)	1.1877 (2)	0.0497 (6)
H7	0.8370	0.0019	1.1370	0.060*
C8	0.9182 (3)	0.07674 (11)	1.2480 (2)	0.0496 (6)
C9	0.9095 (3)	0.11453 (14)	1.3352 (3)	0.0642 (7)
H9	0.8419	0.1094	1.3566	0.077*
C10	0.9998 (3)	0.15966 (15)	1.3905 (3)	0.0721 (8)
H10	0.9925	0.1848	1.4484	0.087*
C11	1.1004 (3)	0.16721 (14)	1.3596 (2)	0.0641 (7)
H11	1.1616	0.1973	1.3974	0.077*
C12	1.1111 (3)	0.13062 (13)	1.2734 (2)	0.0577 (7)
H12	1.1789	0.1363	1.2524	0.069*
C13	1.0217 (2)	0.08554 (12)	1.2180 (2)	0.0499 (6)
C14	1.1296 (3)	0.05037 (14)	1.1008 (3)	0.0640 (7)
H14A	1.1350	0.0124	1.0615	0.077*
H14B	1.2078	0.0546	1.1727	0.077*
C15	1.1167 (3)	0.10434 (17)	1.0195 (3)	0.0712 (8)
C16	1.1906 (13)	0.1507 (5)	0.8951 (12)	0.351 (9)
H16A	1.0988	0.1557	0.8546	0.421*
H16B	1.2167	0.1310	0.8384	0.421*
C17	1.2435 (8)	0.2131 (3)	0.9119 (7)	0.170 (3)
H17A	1.3109	0.2167	0.9905	0.255*
H17B	1.1777	0.2425	0.9025	0.255*
H17C	1.2766	0.2211	0.8538	0.255*
C18	0.4322 (3)	−0.18466 (12)	0.8482 (3)	0.0622 (7)
C19	0.5350 (3)	−0.12858 (14)	0.6412 (3)	0.0598 (7)
H19	0.5493	−0.0881	0.6690	0.072*
C20	0.5563 (3)	−0.14547 (14)	0.5363 (2)	0.0620 (7)
C21	0.5237 (3)	−0.20391 (16)	0.4848 (3)	0.0759 (9)
H21	0.4880	−0.2327	0.5177	0.091*
C22	0.5437 (4)	−0.21969 (19)	0.3858 (3)	0.0829 (10)
H22	0.5205	−0.2586	0.3517	0.100*
C23	0.5977 (4)	−0.17794 (19)	0.3382 (3)	0.0875 (12)
H23	0.6115	−0.1887	0.2718	0.105*
C24	0.6317 (4)	−0.12035 (17)	0.3872 (3)	0.0819 (10)
H24	0.6685	−0.0923	0.3540	0.098*
C25	0.6114 (3)	−0.10395 (14)	0.4863 (2)	0.0665 (8)
C26	0.7136 (5)	−0.00699 (17)	0.5070 (3)	0.0916 (12)
H26A	0.6602	0.0095	0.4288	0.110*
H26B	0.7864	−0.0274	0.5029	0.110*
C27	0.7567 (4)	0.04350 (17)	0.5975 (3)	0.0922 (12)
O5	1.2125 (3)	0.10572 (13)	0.9880 (3)	0.0981 (9)
C28	0.8947 (11)	0.1314 (4)	0.6564 (9)	0.231 (8)	0.905 (13)
H28A	0.9670	0.1425	0.6399	0.278*	0.905 (13)
H28B	0.9264	0.1098	0.7320	0.278*	0.905 (13)
C29	0.8259 (13)	0.1885 (5)	0.6639 (14)	0.306 (9)	0.905 (13)
H29A	0.8077	0.2135	0.5945	0.459*	0.905 (13)
H29B	0.8784	0.2114	0.7339	0.459*	0.905 (13)
H29C	0.7476	0.1774	0.6683	0.459*	0.905 (13)
O8	0.8081 (10)	0.0907 (3)	0.5612 (5)	0.155 (3)	0.905 (13)
O8'	0.8681 (14)	0.0661 (10)	0.589 (2)	0.047 (7)*	0.095 (13)
C28'	0.896 (5)	0.1302 (12)	0.605 (10)	0.23 (7)*	0.095 (13)
H28C	0.8669	0.1504	0.6593	0.277*	0.095 (13)
H28D	0.8721	0.1532	0.5319	0.277*	0.095 (13)
C29'	1.038 (3)	0.111 (6)	0.664 (13)	0.30 (7)*	0.095 (13)
H29D	1.0792	0.1245	0.6148	0.453*	0.095 (13)
H29E	1.0438	0.0668	0.6715	0.453*	0.095 (13)
H29F	1.0786	0.1295	0.7411	0.453*	0.095 (13)
N1	0.47564 (19)	−0.10620 (9)	1.00079 (17)	0.0458 (5)
N2	0.6383 (2)	−0.02049 (9)	1.14131 (17)	0.0475 (5)
H2A	0.6588	−0.0466	1.0999	0.057*
N3	0.7217 (2)	0.02594 (9)	1.20320 (17)	0.0485 (5)
N4	0.4772 (2)	−0.14655 (10)	0.7900 (2)	0.0606 (6)
H4A	0.4935	−0.1087	0.8119	0.073*
N5	0.4975 (2)	−0.16823 (11)	0.6943 (2)	0.0645 (6)
O1	0.48826 (19)	0.01162 (8)	1.20160 (18)	0.0624 (5)
O2	0.4086 (3)	−0.23957 (10)	0.8248 (2)	0.0996 (9)
O3	1.02504 (19)	0.04682 (9)	1.13173 (18)	0.0656 (5)
O4	1.0338 (3)	0.14056 (15)	0.9878 (3)	0.1093 (10)
O6	0.6451 (3)	−0.04805 (10)	0.5434 (2)	0.0817 (7)
O7	0.7445 (4)	0.04619 (14)	0.6864 (3)	0.1194 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0488 (14)	0.0403 (11)	0.0461 (12)	0.0015 (10)	0.0229 (11)	0.0034 (9)
C2	0.0552 (16)	0.0564 (14)	0.0615 (15)	0.0004 (12)	0.0357 (13)	0.0032 (12)
C3	0.0571 (17)	0.0625 (16)	0.0783 (18)	−0.0119 (13)	0.0362 (15)	0.0049 (14)
C4	0.0641 (18)	0.0484 (14)	0.0702 (17)	−0.0156 (12)	0.0294 (15)	−0.0037 (13)
C5	0.0544 (15)	0.0410 (12)	0.0551 (14)	−0.0033 (11)	0.0218 (12)	−0.0011 (10)
C6	0.0559 (15)	0.0435 (12)	0.0435 (11)	−0.0011 (11)	0.0276 (11)	0.0004 (10)
C7	0.0554 (16)	0.0532 (13)	0.0437 (12)	−0.0045 (11)	0.0241 (12)	−0.0040 (10)
C8	0.0541 (16)	0.0523 (13)	0.0404 (12)	−0.0062 (11)	0.0179 (11)	−0.0022 (10)
C9	0.0680 (19)	0.0727 (18)	0.0581 (15)	−0.0111 (15)	0.0326 (14)	−0.0141 (14)
C10	0.081 (2)	0.0769 (19)	0.0575 (16)	−0.0147 (16)	0.0282 (16)	−0.0250 (15)
C11	0.0633 (19)	0.0597 (16)	0.0570 (15)	−0.0138 (13)	0.0132 (14)	−0.0102 (13)
C12	0.0525 (16)	0.0636 (16)	0.0526 (14)	−0.0087 (13)	0.0175 (12)	−0.0044 (12)
C13	0.0470 (15)	0.0558 (14)	0.0430 (12)	−0.0035 (11)	0.0150 (11)	−0.0027 (11)
C14	0.0549 (17)	0.0726 (18)	0.0733 (18)	−0.0041 (14)	0.0354 (15)	−0.0145 (15)
C15	0.067 (2)	0.087 (2)	0.0686 (18)	−0.0041 (18)	0.0376 (17)	−0.0082 (17)
C16	0.193 (11)	0.44 (3)	0.43 (3)	−0.015 (16)	0.141 (14)	0.00 (2)
C17	0.174 (7)	0.146 (5)	0.196 (7)	0.031 (5)	0.084 (6)	0.079 (5)
C18	0.074 (2)	0.0473 (14)	0.0674 (17)	−0.0043 (13)	0.0313 (15)	−0.0132 (13)
C19	0.0563 (17)	0.0623 (16)	0.0621 (15)	−0.0010 (13)	0.0260 (14)	−0.0172 (13)
C20	0.0576 (17)	0.0735 (18)	0.0513 (14)	0.0163 (14)	0.0194 (13)	−0.0088 (13)
C21	0.068 (2)	0.086 (2)	0.0734 (19)	0.0007 (16)	0.0289 (16)	−0.0301 (17)
C22	0.079 (2)	0.094 (2)	0.0650 (19)	0.0171 (19)	0.0195 (18)	−0.0254 (18)
C23	0.107 (3)	0.106 (3)	0.0428 (15)	0.044 (2)	0.0248 (17)	−0.0030 (17)
C24	0.112 (3)	0.086 (2)	0.0483 (15)	0.035 (2)	0.0341 (17)	0.0146 (16)
C25	0.083 (2)	0.0669 (17)	0.0476 (14)	0.0270 (16)	0.0255 (14)	0.0058 (13)
C26	0.147 (4)	0.081 (2)	0.0652 (19)	0.010 (2)	0.063 (2)	0.0169 (17)
C27	0.137 (4)	0.083 (2)	0.077 (2)	0.000 (2)	0.065 (2)	0.0156 (18)
O5	0.0941 (19)	0.0998 (18)	0.129 (2)	0.0022 (15)	0.0749 (19)	0.0165 (16)
C28	0.39 (2)	0.184 (9)	0.194 (9)	−0.151 (12)	0.190 (13)	−0.057 (8)
C29	0.231 (14)	0.303 (19)	0.37 (2)	0.035 (14)	0.113 (15)	0.096 (17)
O8	0.246 (7)	0.139 (4)	0.126 (4)	−0.065 (5)	0.123 (5)	−0.012 (3)
N1	0.0486 (12)	0.0415 (10)	0.0518 (11)	−0.0030 (9)	0.0254 (10)	−0.0039 (9)
N2	0.0548 (13)	0.0465 (10)	0.0472 (10)	−0.0079 (9)	0.0272 (10)	−0.0092 (9)
N3	0.0526 (13)	0.0501 (11)	0.0452 (10)	−0.0082 (9)	0.0230 (9)	−0.0063 (9)
N4	0.0723 (16)	0.0505 (12)	0.0698 (14)	−0.0116 (11)	0.0404 (13)	−0.0221 (11)
N5	0.0727 (17)	0.0625 (14)	0.0621 (13)	−0.0029 (12)	0.0319 (13)	−0.0205 (12)
O1	0.0775 (13)	0.0528 (10)	0.0756 (12)	−0.0095 (9)	0.0504 (11)	−0.0167 (9)
O2	0.162 (3)	0.0512 (12)	0.1062 (18)	−0.0229 (14)	0.0769 (19)	−0.0250 (12)
O3	0.0621 (12)	0.0755 (12)	0.0701 (12)	−0.0208 (10)	0.0384 (10)	−0.0258 (10)
O4	0.108 (2)	0.129 (2)	0.109 (2)	0.0452 (19)	0.0635 (18)	0.0369 (18)
O6	0.126 (2)	0.0663 (13)	0.0724 (13)	0.0102 (13)	0.0610 (14)	0.0051 (11)
O7	0.193 (3)	0.106 (2)	0.0978 (19)	−0.028 (2)	0.099 (2)	−0.0171 (15)

Geometric parameters (Å, º) top

C1—N1	1.334 (3)	C18—N4	1.336 (4)
C1—C2	1.389 (3)	C19—N5	1.263 (4)
C1—C6	1.498 (3)	C19—C20	1.463 (4)
C2—C3	1.375 (4)	C19—H19	0.9300
C2—H2	0.9300	C20—C25	1.388 (4)
C3—C4	1.374 (4)	C20—C21	1.396 (4)
C3—H3	0.9300	C21—C22	1.380 (4)
C4—C5	1.383 (4)	C21—H21	0.9300
C4—H4	0.9300	C22—C23	1.363 (6)
C5—N1	1.335 (3)	C22—H22	0.9300
C5—C18	1.496 (4)	C23—C24	1.370 (5)
C6—O1	1.215 (3)	C23—H23	0.9300
C6—N2	1.348 (3)	C24—C25	1.386 (4)
C7—N3	1.267 (3)	C24—H24	0.9300
C7—C8	1.455 (4)	C25—O6	1.373 (4)
C7—H7	0.9300	C26—O6	1.385 (4)
C8—C9	1.390 (4)	C26—C27	1.493 (5)
C8—C13	1.404 (4)	C26—H26A	0.9700
C9—C10	1.383 (4)	C26—H26B	0.9700
C9—H9	0.9300	C27—O7	1.167 (4)
C10—C11	1.377 (4)	C27—O8	1.349 (5)
C10—H10	0.9300	C27—O8'	1.419 (10)
C11—C12	1.375 (4)	C28—O8	1.475 (7)
C11—H11	0.9300	C28—C29	1.494 (9)
C12—C13	1.377 (4)	C28—H28A	0.9700
C12—H12	0.9300	C28—H28B	0.9700
C13—O3	1.370 (3)	C29—H29A	0.9600
C14—O3	1.413 (3)	C29—H29B	0.9600
C14—C15	1.508 (5)	C29—H29C	0.9600
C14—H14A	0.9700	O8'—C28'	1.420 (10)
C14—H14B	0.9700	C28'—C29'	1.540 (11)
C15—O4	1.171 (4)	C28'—H28C	0.9700
C15—O5	1.318 (4)	C28'—H28D	0.9700
C16—O5	1.447 (9)	C29'—H29D	0.9600
C16—C17	1.460 (9)	C29'—H29E	0.9600
C16—H16A	0.9700	C29'—H29F	0.9600
C16—H16B	0.9700	N2—N3	1.381 (3)
C17—H17A	0.9600	N2—H2A	0.8600
C17—H17B	0.9600	N4—N5	1.380 (3)
C17—H17C	0.9600	N4—H4A	0.8600
C18—O2	1.228 (3)

N1—C1—C2	123.8 (2)	N5—C19—H19	119.6
N1—C1—C6	117.4 (2)	C20—C19—H19	119.6
C2—C1—C6	118.9 (2)	C25—C20—C21	118.1 (3)
C3—C2—C1	118.1 (2)	C25—C20—C19	120.7 (3)
C3—C2—H2	120.9	C21—C20—C19	121.2 (3)
C1—C2—H2	120.9	C22—C21—C20	121.1 (4)
C4—C3—C2	119.0 (2)	C22—C21—H21	119.5
C4—C3—H3	120.5	C20—C21—H21	119.5
C2—C3—H3	120.5	C23—C22—C21	119.6 (3)
C3—C4—C5	118.9 (2)	C23—C22—H22	120.2
C3—C4—H4	120.6	C21—C22—H22	120.2
C5—C4—H4	120.6	C22—C23—C24	120.8 (3)
N1—C5—C4	123.3 (2)	C22—C23—H23	119.6
N1—C5—C18	118.1 (2)	C24—C23—H23	119.6
C4—C5—C18	118.5 (2)	C23—C24—C25	120.0 (4)
O1—C6—N2	123.9 (2)	C23—C24—H24	120.0
O1—C6—C1	121.7 (2)	C25—C24—H24	120.0
N2—C6—C1	114.32 (19)	O6—C25—C24	124.3 (3)
N3—C7—C8	121.0 (2)	O6—C25—C20	115.2 (2)
N3—C7—H7	119.5	C24—C25—C20	120.5 (3)
C8—C7—H7	119.5	O6—C26—C27	106.5 (3)
C9—C8—C13	118.1 (2)	O6—C26—H26A	110.4
C9—C8—C7	121.7 (2)	C27—C26—H26A	110.4
C13—C8—C7	120.2 (2)	O6—C26—H26B	110.4
C10—C9—C8	121.0 (3)	C27—C26—H26B	110.4
C10—C9—H9	119.5	H26A—C26—H26B	108.6
C8—C9—H9	119.5	O7—C27—O8	121.3 (4)
C11—C10—C9	119.7 (3)	O7—C27—O8'	121.4 (10)
C11—C10—H10	120.2	O8—C27—O8'	34.6 (7)
C9—C10—H10	120.2	O7—C27—C26	127.5 (3)
C12—C11—C10	120.5 (3)	O8—C27—C26	111.2 (3)
C12—C11—H11	119.7	O8'—C27—C26	103.2 (10)
C10—C11—H11	119.7	C15—O5—C16	111.2 (6)
C11—C12—C13	120.1 (3)	O8—C28—C29	110.2 (9)
C11—C12—H12	120.0	O8—C28—H28A	109.6
C13—C12—H12	120.0	C29—C28—H28A	109.6
O3—C13—C12	124.1 (2)	O8—C28—H28B	109.6
O3—C13—C8	115.3 (2)	C29—C28—H28B	109.6
C12—C13—C8	120.6 (2)	H28A—C28—H28B	108.1
O3—C14—C15	111.4 (3)	C27—O8—C28	115.7 (5)
O3—C14—H14A	109.3	C27—O8'—C28'	119.3 (13)
C15—C14—H14A	109.3	O8'—C28'—C29'	86 (2)
O3—C14—H14B	109.3	O8'—C28'—H28C	114.2
C15—C14—H14B	109.3	C29'—C28'—H28C	114.2
H14A—C14—H14B	108.0	O8'—C28'—H28D	114.2
O4—C15—O5	123.8 (3)	C29'—C28'—H28D	114.2
O4—C15—C14	125.6 (3)	H28C—C28'—H28D	111.4
O5—C15—C14	110.7 (3)	C28'—C29'—H29D	109.5
O5—C16—C17	125.9 (10)	C28'—C29'—H29E	109.5
O5—C16—H16A	105.8	H29D—C29'—H29E	109.5
C17—C16—H16A	105.8	C28'—C29'—H29F	109.5
O5—C16—H16B	105.8	H29D—C29'—H29F	109.5
C17—C16—H16B	105.8	H29E—C29'—H29F	109.5
H16A—C16—H16B	106.2	C1—N1—C5	116.9 (2)
C16—C17—H17A	109.5	C6—N2—N3	119.08 (19)
C16—C17—H17B	109.5	C6—N2—H2A	120.5
H17A—C17—H17B	109.5	N3—N2—H2A	120.5
C16—C17—H17C	109.5	C7—N3—N2	115.9 (2)
H17A—C17—H17C	109.5	C18—N4—N5	119.7 (2)
H17B—C17—H17C	109.5	C18—N4—H4A	120.1
O2—C18—N4	124.7 (3)	N5—N4—H4A	120.1
O2—C18—C5	120.4 (3)	C19—N5—N4	115.6 (2)
N4—C18—C5	114.8 (2)	C13—O3—C14	118.9 (2)
N5—C19—C20	120.8 (3)	C25—O6—C26	118.5 (2)

N1—C1—C2—C3	1.8 (4)	C23—C24—C25—C20	−0.2 (5)
C6—C1—C2—C3	−178.0 (2)	C21—C20—C25—O6	−177.9 (3)
C1—C2—C3—C4	−0.5 (4)	C19—C20—C25—O6	1.1 (4)
C2—C3—C4—C5	−1.6 (4)	C21—C20—C25—C24	0.7 (4)
C3—C4—C5—N1	2.7 (4)	C19—C20—C25—C24	179.7 (3)
C3—C4—C5—C18	−175.0 (3)	O6—C26—C27—O7	5.4 (7)
N1—C1—C6—O1	163.9 (2)	O6—C26—C27—O8	−170.8 (6)
C2—C1—C6—O1	−16.3 (4)	O6—C26—C27—O8'	153.9 (10)
N1—C1—C6—N2	−17.8 (3)	O4—C15—O5—C16	−9.6 (8)
C2—C1—C6—N2	162.0 (2)	C14—C15—O5—C16	170.5 (6)
N3—C7—C8—C9	7.8 (4)	C17—C16—O5—C15	99.1 (12)
N3—C7—C8—C13	−171.5 (2)	O7—C27—O8—C28	25.2 (11)
C13—C8—C9—C10	0.2 (4)	O8'—C27—O8—C28	−75.9 (19)
C7—C8—C9—C10	−179.1 (3)	C26—C27—O8—C28	−158.4 (7)
C8—C9—C10—C11	−0.4 (5)	C29—C28—O8—C27	−99.3 (11)
C9—C10—C11—C12	0.6 (5)	O7—C27—O8'—C28'	−64 (6)
C10—C11—C12—C13	−0.7 (4)	O8—C27—O8'—C28'	37 (5)
C11—C12—C13—O3	−179.7 (3)	C26—C27—O8'—C28'	145 (5)
C11—C12—C13—C8	0.5 (4)	C27—O8'—C28'—C29'	146 (7)
C9—C8—C13—O3	179.9 (2)	C2—C1—N1—C5	−0.8 (4)
C7—C8—C13—O3	−0.8 (4)	C6—C1—N1—C5	179.0 (2)
C9—C8—C13—C12	−0.3 (4)	C4—C5—N1—C1	−1.5 (4)
C7—C8—C13—C12	179.0 (2)	C18—C5—N1—C1	176.2 (2)
O3—C14—C15—O4	2.4 (5)	O1—C6—N2—N3	1.3 (4)
O3—C14—C15—O5	−177.7 (3)	C1—C6—N2—N3	−176.90 (19)
N1—C5—C18—O2	152.8 (3)	C8—C7—N3—N2	179.9 (2)
C4—C5—C18—O2	−29.3 (4)	C6—N2—N3—C7	−175.1 (2)
N1—C5—C18—N4	−29.8 (4)	O2—C18—N4—N5	1.4 (5)
C4—C5—C18—N4	148.0 (3)	C5—C18—N4—N5	−175.8 (2)
N5—C19—C20—C25	−172.5 (3)	C20—C19—N5—N4	−178.2 (2)
N5—C19—C20—C21	6.6 (5)	C18—N4—N5—C19	177.1 (3)
C25—C20—C21—C22	−1.0 (5)	C12—C13—O3—C14	3.5 (4)
C19—C20—C21—C22	179.9 (3)	C8—C13—O3—C14	−176.6 (2)
C20—C21—C22—C23	0.9 (5)	C15—C14—O3—C13	−78.7 (3)
C21—C22—C23—C24	−0.3 (5)	C24—C25—O6—C26	−5.8 (5)
C22—C23—C24—C25	0.0 (5)	C20—C25—O6—C26	172.7 (3)
C23—C24—C25—O6	178.3 (3)	C27—C26—O6—C25	−169.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.53	3.353 (3)	161
C2—H2···O7ⁱⁱ	0.93	2.40	3.304 (4)	165
C17—H17C···O2ⁱⁱⁱ	0.96	2.49	2.896 (8)	105
N2—H2A···N1	0.86	2.34	2.694 (3)	105

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+3/2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₉H₂₉N₅O₈
M_r	575.57
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	299
a, b, c (Å)	11.5485 (6), 21.6606 (11), 12.3596 (9)
β (°)	114.779 (1)
V (Å³)	2807.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23685, 6101, 4136
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.076, 0.231, 1.04
No. of reflections	6101
No. of parameters	396
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.52

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O5ⁱ	0.86	2.53	3.353 (3)	161.4
C2—H2···O7ⁱⁱ	0.93	2.40	3.304 (4)	165.1
C17—H17C···O2ⁱⁱⁱ	0.96	2.49	2.896 (8)	105.1
N2—H2A···N1	0.86	2.34	2.694 (3)	105.1

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+2; (iii) −x+3/2, y+1/2, −z+3/2.

Acknowledgements

This work was supported by Hubei Education Department, Government of China (grant No. 20040131).

References

Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, X., Zhan, S., Hu, C., Meng, Q. & Liu, Y. (1997). J. Chem. Soc. Dalton Trans. pp. 245–250. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2001). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Thompson, L. K. (2002). Coord. Chem. Rev. 233–234, 193–206. Web of Science CrossRef CAS Google Scholar
Zhao, L., Xu, Z., Grove, H. & Milway, V. A. (2004). Inorg. Chem. 43, 3812–3824. Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.