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

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ISSN: 2056-9890

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

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[Chen, X., Zhan, S., Hu, C., Meng, Q. & Liu, Y. (1997). J. Chem. Soc. Dalton Trans. pp. 245-250.]); Thompson (2002[Thompson, L. K. (2002). Coord. Chem. Rev. 233-234, 193-206.]); Zhao et al. (2004[Zhao, L., Xu, Z., Grove, H. & Milway, V. A. (2004). Inorg. Chem. 43, 3812-3824.]).

[Scheme 1]

Experimental

Crystal data
  • C29H29N5O8

  • Mr = 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)

  • Rint = 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

  • Δρmax = 0.40 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Sheldrick, 2001[Sheldrick, G. M. (2001). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

After their location in the difference map, all H-atoms were fixed geometrically at ideal positions and allowed to ride on the parent C or N atoms with C—H = 0.93Å and N—H = 0.86Å and Uiso(H)= 1.2Ueq(C and N). The esterified group is disorder over two sites. So, the site-occupancy factors for the two orientations were refined as 0.905 / 0.095. The SHELX restrains AFIX, FLAT and ISOR were applied.

Structure description 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).

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
[Figure 1] Fig. 1. The structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 20% probability level.
[Figure 2] Fig. 2. A view of the packing of (I). Hydrogen bonds are shown by dashed lines.
N2,N2'—Bis[2-(ethoxycarbonylmethoxy)benzylidene]pyridine- 2,6-dicarbohydrazide top
Crystal data top
C29H29N5O8Z = 4
Mr = 575.57F(000) = 1208
Monoclinic, P21/nDx = 1.362 Mg m3
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 11.5485 (6) ŵ = 0.10 mm1
b = 21.6606 (11) ÅT = 299 K
c = 12.3596 (9) ÅBlock, 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 tubeRint = 0.032
Graphite monochromatorθmax = 27.0°, θmin = 1.9°
phi and ω scansh = 1414
23685 measured reflectionsk = 2727
6101 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.231H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.1307P)2 + 0.5522P]
where P = (Fo2 + 2Fc2)/3
6101 reflections(Δ/σ)max < 0.001
396 parametersΔρmax = 0.40 e Å3
12 restraintsΔρmin = 0.52 e Å3
Crystal data top
C29H29N5O8V = 2807.1 (3) Å3
Mr = 575.57Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.5485 (6) ŵ = 0.10 mm1
b = 21.6606 (11) ÅT = 299 K
c = 12.3596 (9) Å0.32 × 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 reflectionsRint = 0.032
6101 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07612 restraints
wR(F2) = 0.231H-atom parameters constrained
S = 1.04Δρmax = 0.40 e Å3
6101 reflectionsΔρmin = 0.52 e Å3
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
xyzUiso*/UeqOcc. (<1)
C10.4448 (2)0.07839 (10)1.0814 (2)0.0440 (5)
C20.3444 (3)0.09691 (12)1.1079 (2)0.0539 (6)
H20.32470.07551.16320.065*
C30.2749 (3)0.14779 (13)1.0499 (3)0.0633 (7)
H30.20740.16171.06580.076*
C40.3065 (3)0.17779 (12)0.9680 (3)0.0605 (7)
H40.26220.21290.92910.073*
C50.4054 (3)0.15491 (11)0.9445 (2)0.0506 (6)
C60.5243 (2)0.02429 (11)1.1467 (2)0.0453 (5)
C70.8231 (2)0.02966 (12)1.1877 (2)0.0497 (6)
H70.83700.00191.13700.060*
C80.9182 (3)0.07674 (11)1.2480 (2)0.0496 (6)
C90.9095 (3)0.11453 (14)1.3352 (3)0.0642 (7)
H90.84190.10941.35660.077*
C100.9998 (3)0.15966 (15)1.3905 (3)0.0721 (8)
H100.99250.18481.44840.087*
C111.1004 (3)0.16721 (14)1.3596 (2)0.0641 (7)
H111.16160.19731.39740.077*
C121.1111 (3)0.13062 (13)1.2734 (2)0.0577 (7)
H121.17890.13631.25240.069*
C131.0217 (2)0.08554 (12)1.2180 (2)0.0499 (6)
C141.1296 (3)0.05037 (14)1.1008 (3)0.0640 (7)
H14A1.13500.01241.06150.077*
H14B1.20780.05461.17270.077*
C151.1167 (3)0.10434 (17)1.0195 (3)0.0712 (8)
C161.1906 (13)0.1507 (5)0.8951 (12)0.351 (9)
H16A1.09880.15570.85460.421*
H16B1.21670.13100.83840.421*
C171.2435 (8)0.2131 (3)0.9119 (7)0.170 (3)
H17A1.31090.21670.99050.255*
H17B1.17770.24250.90250.255*
H17C1.27660.22110.85380.255*
C180.4322 (3)0.18466 (12)0.8482 (3)0.0622 (7)
C190.5350 (3)0.12858 (14)0.6412 (3)0.0598 (7)
H190.54930.08810.66900.072*
C200.5563 (3)0.14547 (14)0.5363 (2)0.0620 (7)
C210.5237 (3)0.20391 (16)0.4848 (3)0.0759 (9)
H210.48800.23270.51770.091*
C220.5437 (4)0.21969 (19)0.3858 (3)0.0829 (10)
H220.52050.25860.35170.100*
C230.5977 (4)0.17794 (19)0.3382 (3)0.0875 (12)
H230.61150.18870.27180.105*
C240.6317 (4)0.12035 (17)0.3872 (3)0.0819 (10)
H240.66850.09230.35400.098*
C250.6114 (3)0.10395 (14)0.4863 (2)0.0665 (8)
C260.7136 (5)0.00699 (17)0.5070 (3)0.0916 (12)
H26A0.66020.00950.42880.110*
H26B0.78640.02740.50290.110*
C270.7567 (4)0.04350 (17)0.5975 (3)0.0922 (12)
O51.2125 (3)0.10572 (13)0.9880 (3)0.0981 (9)
C280.8947 (11)0.1314 (4)0.6564 (9)0.231 (8)0.905 (13)
H28A0.96700.14250.63990.278*0.905 (13)
H28B0.92640.10980.73200.278*0.905 (13)
C290.8259 (13)0.1885 (5)0.6639 (14)0.306 (9)0.905 (13)
H29A0.80770.21350.59450.459*0.905 (13)
H29B0.87840.21140.73390.459*0.905 (13)
H29C0.74760.17740.66830.459*0.905 (13)
O80.8081 (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)
H28C0.86690.15040.65930.277*0.095 (13)
H28D0.87210.15320.53190.277*0.095 (13)
C29'1.038 (3)0.111 (6)0.664 (13)0.30 (7)*0.095 (13)
H29D1.07920.12450.61480.453*0.095 (13)
H29E1.04380.06680.67150.453*0.095 (13)
H29F1.07860.12950.74110.453*0.095 (13)
N10.47564 (19)0.10620 (9)1.00079 (17)0.0458 (5)
N20.6383 (2)0.02049 (9)1.14131 (17)0.0475 (5)
H2A0.65880.04661.09990.057*
N30.7217 (2)0.02594 (9)1.20320 (17)0.0485 (5)
N40.4772 (2)0.14655 (10)0.7900 (2)0.0606 (6)
H4A0.49350.10870.81190.073*
N50.4975 (2)0.16823 (11)0.6943 (2)0.0645 (6)
O10.48826 (19)0.01162 (8)1.20160 (18)0.0624 (5)
O20.4086 (3)0.23957 (10)0.8248 (2)0.0996 (9)
O31.02504 (19)0.04682 (9)1.13173 (18)0.0656 (5)
O41.0338 (3)0.14056 (15)0.9878 (3)0.1093 (10)
O60.6451 (3)0.04805 (10)0.5434 (2)0.0817 (7)
O70.7445 (4)0.04619 (14)0.6864 (3)0.1194 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0488 (14)0.0403 (11)0.0461 (12)0.0015 (10)0.0229 (11)0.0034 (9)
C20.0552 (16)0.0564 (14)0.0615 (15)0.0004 (12)0.0357 (13)0.0032 (12)
C30.0571 (17)0.0625 (16)0.0783 (18)0.0119 (13)0.0362 (15)0.0049 (14)
C40.0641 (18)0.0484 (14)0.0702 (17)0.0156 (12)0.0294 (15)0.0037 (13)
C50.0544 (15)0.0410 (12)0.0551 (14)0.0033 (11)0.0218 (12)0.0011 (10)
C60.0559 (15)0.0435 (12)0.0435 (11)0.0011 (11)0.0276 (11)0.0004 (10)
C70.0554 (16)0.0532 (13)0.0437 (12)0.0045 (11)0.0241 (12)0.0040 (10)
C80.0541 (16)0.0523 (13)0.0404 (12)0.0062 (11)0.0179 (11)0.0022 (10)
C90.0680 (19)0.0727 (18)0.0581 (15)0.0111 (15)0.0326 (14)0.0141 (14)
C100.081 (2)0.0769 (19)0.0575 (16)0.0147 (16)0.0282 (16)0.0250 (15)
C110.0633 (19)0.0597 (16)0.0570 (15)0.0138 (13)0.0132 (14)0.0102 (13)
C120.0525 (16)0.0636 (16)0.0526 (14)0.0087 (13)0.0175 (12)0.0044 (12)
C130.0470 (15)0.0558 (14)0.0430 (12)0.0035 (11)0.0150 (11)0.0027 (11)
C140.0549 (17)0.0726 (18)0.0733 (18)0.0041 (14)0.0354 (15)0.0145 (15)
C150.067 (2)0.087 (2)0.0686 (18)0.0041 (18)0.0376 (17)0.0082 (17)
C160.193 (11)0.44 (3)0.43 (3)0.015 (16)0.141 (14)0.00 (2)
C170.174 (7)0.146 (5)0.196 (7)0.031 (5)0.084 (6)0.079 (5)
C180.074 (2)0.0473 (14)0.0674 (17)0.0043 (13)0.0313 (15)0.0132 (13)
C190.0563 (17)0.0623 (16)0.0621 (15)0.0010 (13)0.0260 (14)0.0172 (13)
C200.0576 (17)0.0735 (18)0.0513 (14)0.0163 (14)0.0194 (13)0.0088 (13)
C210.068 (2)0.086 (2)0.0734 (19)0.0007 (16)0.0289 (16)0.0301 (17)
C220.079 (2)0.094 (2)0.0650 (19)0.0171 (19)0.0195 (18)0.0254 (18)
C230.107 (3)0.106 (3)0.0428 (15)0.044 (2)0.0248 (17)0.0030 (17)
C240.112 (3)0.086 (2)0.0483 (15)0.035 (2)0.0341 (17)0.0146 (16)
C250.083 (2)0.0669 (17)0.0476 (14)0.0270 (16)0.0255 (14)0.0058 (13)
C260.147 (4)0.081 (2)0.0652 (19)0.010 (2)0.063 (2)0.0169 (17)
C270.137 (4)0.083 (2)0.077 (2)0.000 (2)0.065 (2)0.0156 (18)
O50.0941 (19)0.0998 (18)0.129 (2)0.0022 (15)0.0749 (19)0.0165 (16)
C280.39 (2)0.184 (9)0.194 (9)0.151 (12)0.190 (13)0.057 (8)
C290.231 (14)0.303 (19)0.37 (2)0.035 (14)0.113 (15)0.096 (17)
O80.246 (7)0.139 (4)0.126 (4)0.065 (5)0.123 (5)0.012 (3)
N10.0486 (12)0.0415 (10)0.0518 (11)0.0030 (9)0.0254 (10)0.0039 (9)
N20.0548 (13)0.0465 (10)0.0472 (10)0.0079 (9)0.0272 (10)0.0092 (9)
N30.0526 (13)0.0501 (11)0.0452 (10)0.0082 (9)0.0230 (9)0.0063 (9)
N40.0723 (16)0.0505 (12)0.0698 (14)0.0116 (11)0.0404 (13)0.0221 (11)
N50.0727 (17)0.0625 (14)0.0621 (13)0.0029 (12)0.0319 (13)0.0205 (12)
O10.0775 (13)0.0528 (10)0.0756 (12)0.0095 (9)0.0504 (11)0.0167 (9)
O20.162 (3)0.0512 (12)0.1062 (18)0.0229 (14)0.0769 (19)0.0250 (12)
O30.0621 (12)0.0755 (12)0.0701 (12)0.0208 (10)0.0384 (10)0.0258 (10)
O40.108 (2)0.129 (2)0.109 (2)0.0452 (19)0.0635 (18)0.0369 (18)
O60.126 (2)0.0663 (13)0.0724 (13)0.0102 (13)0.0610 (14)0.0051 (11)
O70.193 (3)0.106 (2)0.0978 (19)0.028 (2)0.099 (2)0.0171 (15)
Geometric parameters (Å, º) top
C1—N11.334 (3)C18—N41.336 (4)
C1—C21.389 (3)C19—N51.263 (4)
C1—C61.498 (3)C19—C201.463 (4)
C2—C31.375 (4)C19—H190.9300
C2—H20.9300C20—C251.388 (4)
C3—C41.374 (4)C20—C211.396 (4)
C3—H30.9300C21—C221.380 (4)
C4—C51.383 (4)C21—H210.9300
C4—H40.9300C22—C231.363 (6)
C5—N11.335 (3)C22—H220.9300
C5—C181.496 (4)C23—C241.370 (5)
C6—O11.215 (3)C23—H230.9300
C6—N21.348 (3)C24—C251.386 (4)
C7—N31.267 (3)C24—H240.9300
C7—C81.455 (4)C25—O61.373 (4)
C7—H70.9300C26—O61.385 (4)
C8—C91.390 (4)C26—C271.493 (5)
C8—C131.404 (4)C26—H26A0.9700
C9—C101.383 (4)C26—H26B0.9700
C9—H90.9300C27—O71.167 (4)
C10—C111.377 (4)C27—O81.349 (5)
C10—H100.9300C27—O8'1.419 (10)
C11—C121.375 (4)C28—O81.475 (7)
C11—H110.9300C28—C291.494 (9)
C12—C131.377 (4)C28—H28A0.9700
C12—H120.9300C28—H28B0.9700
C13—O31.370 (3)C29—H29A0.9600
C14—O31.413 (3)C29—H29B0.9600
C14—C151.508 (5)C29—H29C0.9600
C14—H14A0.9700O8'—C28'1.420 (10)
C14—H14B0.9700C28'—C29'1.540 (11)
C15—O41.171 (4)C28'—H28C0.9700
C15—O51.318 (4)C28'—H28D0.9700
C16—O51.447 (9)C29'—H29D0.9600
C16—C171.460 (9)C29'—H29E0.9600
C16—H16A0.9700C29'—H29F0.9600
C16—H16B0.9700N2—N31.381 (3)
C17—H17A0.9600N2—H2A0.8600
C17—H17B0.9600N4—N51.380 (3)
C17—H17C0.9600N4—H4A0.8600
C18—O21.228 (3)
N1—C1—C2123.8 (2)N5—C19—H19119.6
N1—C1—C6117.4 (2)C20—C19—H19119.6
C2—C1—C6118.9 (2)C25—C20—C21118.1 (3)
C3—C2—C1118.1 (2)C25—C20—C19120.7 (3)
C3—C2—H2120.9C21—C20—C19121.2 (3)
C1—C2—H2120.9C22—C21—C20121.1 (4)
C4—C3—C2119.0 (2)C22—C21—H21119.5
C4—C3—H3120.5C20—C21—H21119.5
C2—C3—H3120.5C23—C22—C21119.6 (3)
C3—C4—C5118.9 (2)C23—C22—H22120.2
C3—C4—H4120.6C21—C22—H22120.2
C5—C4—H4120.6C22—C23—C24120.8 (3)
N1—C5—C4123.3 (2)C22—C23—H23119.6
N1—C5—C18118.1 (2)C24—C23—H23119.6
C4—C5—C18118.5 (2)C23—C24—C25120.0 (4)
O1—C6—N2123.9 (2)C23—C24—H24120.0
O1—C6—C1121.7 (2)C25—C24—H24120.0
N2—C6—C1114.32 (19)O6—C25—C24124.3 (3)
N3—C7—C8121.0 (2)O6—C25—C20115.2 (2)
N3—C7—H7119.5C24—C25—C20120.5 (3)
C8—C7—H7119.5O6—C26—C27106.5 (3)
C9—C8—C13118.1 (2)O6—C26—H26A110.4
C9—C8—C7121.7 (2)C27—C26—H26A110.4
C13—C8—C7120.2 (2)O6—C26—H26B110.4
C10—C9—C8121.0 (3)C27—C26—H26B110.4
C10—C9—H9119.5H26A—C26—H26B108.6
C8—C9—H9119.5O7—C27—O8121.3 (4)
C11—C10—C9119.7 (3)O7—C27—O8'121.4 (10)
C11—C10—H10120.2O8—C27—O8'34.6 (7)
C9—C10—H10120.2O7—C27—C26127.5 (3)
C12—C11—C10120.5 (3)O8—C27—C26111.2 (3)
C12—C11—H11119.7O8'—C27—C26103.2 (10)
C10—C11—H11119.7C15—O5—C16111.2 (6)
C11—C12—C13120.1 (3)O8—C28—C29110.2 (9)
C11—C12—H12120.0O8—C28—H28A109.6
C13—C12—H12120.0C29—C28—H28A109.6
O3—C13—C12124.1 (2)O8—C28—H28B109.6
O3—C13—C8115.3 (2)C29—C28—H28B109.6
C12—C13—C8120.6 (2)H28A—C28—H28B108.1
O3—C14—C15111.4 (3)C27—O8—C28115.7 (5)
O3—C14—H14A109.3C27—O8'—C28'119.3 (13)
C15—C14—H14A109.3O8'—C28'—C29'86 (2)
O3—C14—H14B109.3O8'—C28'—H28C114.2
C15—C14—H14B109.3C29'—C28'—H28C114.2
H14A—C14—H14B108.0O8'—C28'—H28D114.2
O4—C15—O5123.8 (3)C29'—C28'—H28D114.2
O4—C15—C14125.6 (3)H28C—C28'—H28D111.4
O5—C15—C14110.7 (3)C28'—C29'—H29D109.5
O5—C16—C17125.9 (10)C28'—C29'—H29E109.5
O5—C16—H16A105.8H29D—C29'—H29E109.5
C17—C16—H16A105.8C28'—C29'—H29F109.5
O5—C16—H16B105.8H29D—C29'—H29F109.5
C17—C16—H16B105.8H29E—C29'—H29F109.5
H16A—C16—H16B106.2C1—N1—C5116.9 (2)
C16—C17—H17A109.5C6—N2—N3119.08 (19)
C16—C17—H17B109.5C6—N2—H2A120.5
H17A—C17—H17B109.5N3—N2—H2A120.5
C16—C17—H17C109.5C7—N3—N2115.9 (2)
H17A—C17—H17C109.5C18—N4—N5119.7 (2)
H17B—C17—H17C109.5C18—N4—H4A120.1
O2—C18—N4124.7 (3)N5—N4—H4A120.1
O2—C18—C5120.4 (3)C19—N5—N4115.6 (2)
N4—C18—C5114.8 (2)C13—O3—C14118.9 (2)
N5—C19—C20120.8 (3)C25—O6—C26118.5 (2)
N1—C1—C2—C31.8 (4)C23—C24—C25—C200.2 (5)
C6—C1—C2—C3178.0 (2)C21—C20—C25—O6177.9 (3)
C1—C2—C3—C40.5 (4)C19—C20—C25—O61.1 (4)
C2—C3—C4—C51.6 (4)C21—C20—C25—C240.7 (4)
C3—C4—C5—N12.7 (4)C19—C20—C25—C24179.7 (3)
C3—C4—C5—C18175.0 (3)O6—C26—C27—O75.4 (7)
N1—C1—C6—O1163.9 (2)O6—C26—C27—O8170.8 (6)
C2—C1—C6—O116.3 (4)O6—C26—C27—O8'153.9 (10)
N1—C1—C6—N217.8 (3)O4—C15—O5—C169.6 (8)
C2—C1—C6—N2162.0 (2)C14—C15—O5—C16170.5 (6)
N3—C7—C8—C97.8 (4)C17—C16—O5—C1599.1 (12)
N3—C7—C8—C13171.5 (2)O7—C27—O8—C2825.2 (11)
C13—C8—C9—C100.2 (4)O8'—C27—O8—C2875.9 (19)
C7—C8—C9—C10179.1 (3)C26—C27—O8—C28158.4 (7)
C8—C9—C10—C110.4 (5)C29—C28—O8—C2799.3 (11)
C9—C10—C11—C120.6 (5)O7—C27—O8'—C28'64 (6)
C10—C11—C12—C130.7 (4)O8—C27—O8'—C28'37 (5)
C11—C12—C13—O3179.7 (3)C26—C27—O8'—C28'145 (5)
C11—C12—C13—C80.5 (4)C27—O8'—C28'—C29'146 (7)
C9—C8—C13—O3179.9 (2)C2—C1—N1—C50.8 (4)
C7—C8—C13—O30.8 (4)C6—C1—N1—C5179.0 (2)
C9—C8—C13—C120.3 (4)C4—C5—N1—C11.5 (4)
C7—C8—C13—C12179.0 (2)C18—C5—N1—C1176.2 (2)
O3—C14—C15—O42.4 (5)O1—C6—N2—N31.3 (4)
O3—C14—C15—O5177.7 (3)C1—C6—N2—N3176.90 (19)
N1—C5—C18—O2152.8 (3)C8—C7—N3—N2179.9 (2)
C4—C5—C18—O229.3 (4)C6—N2—N3—C7175.1 (2)
N1—C5—C18—N429.8 (4)O2—C18—N4—N51.4 (5)
C4—C5—C18—N4148.0 (3)C5—C18—N4—N5175.8 (2)
N5—C19—C20—C25172.5 (3)C20—C19—N5—N4178.2 (2)
N5—C19—C20—C216.6 (5)C18—N4—N5—C19177.1 (3)
C25—C20—C21—C221.0 (5)C12—C13—O3—C143.5 (4)
C19—C20—C21—C22179.9 (3)C8—C13—O3—C14176.6 (2)
C20—C21—C22—C230.9 (5)C15—C14—O3—C1378.7 (3)
C21—C22—C23—C240.3 (5)C24—C25—O6—C265.8 (5)
C22—C23—C24—C250.0 (5)C20—C25—O6—C26172.7 (3)
C23—C24—C25—O6178.3 (3)C27—C26—O6—C25169.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O5i0.862.533.353 (3)161
C2—H2···O7ii0.932.403.304 (4)165
C17—H17C···O2iii0.962.492.896 (8)105
N2—H2A···N10.862.342.694 (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 formulaC29H29N5O8
Mr575.57
Crystal system, space groupMonoclinic, P21/n
Temperature (K)299
a, b, c (Å)11.5485 (6), 21.6606 (11), 12.3596 (9)
β (°) 114.779 (1)
V3)2807.1 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.32 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
23685, 6101, 4136
Rint0.032
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.231, 1.04
No. of reflections6101
No. of parameters396
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2A···O5i0.862.533.353 (3)161.4
C2—H2···O7ii0.932.403.304 (4)165.1
C17—H17C···O2iii0.962.492.896 (8)105.1
N2—H2A···N10.862.342.694 (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

First citationBruker (2001). SAINT-Plus (Version 6.45) and SMART (Version 5.628). Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationChen, 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
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2001). SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationThompson, L. K. (2002). Coord. Chem. Rev. 233–234, 193–206.  Web of Science CrossRef CAS Google Scholar
First citationZhao, L., Xu, Z., Grove, H. & Milway, V. A. (2004). Inorg. Chem. 43, 3812–3824.  Web of Science CSD CrossRef PubMed CAS Google Scholar

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