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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o185.
Published online 2007 December 6. doi:  10.1107/S160053680706477X
PMCID: PMC2915248

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

Abstract

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 [triangle]); Thompson (2002 [triangle]); Zhao et al. (2004 [triangle]).

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Object name is e-64-0o185-scheme1.jpg

Experimental

Crystal data

  • C29H29N5O8
  • M r = 575.57
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o185-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.076
  • wR(F 2) = 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

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706477X/bq2047Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

C29H29N5O8Z = 4
Mr = 575.57F000 = 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 (2) K
c = 12.3596 (9) ÅBlock, colorless
β = 114.779 (1)º0.32 × 0.10 × 0.10 mm
V = 2807.1 (3) Å3

Data collection

Bruker SMART CCD area-detector diffractometer4136 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.032
Monochromator: graphiteθmax = 27.0º
T = 299(2) Kθmin = 1.9º
phi and ω scansh = −14→14
Absorption correction: nonek = −27→27
23685 measured reflectionsl = −15→15
6101 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.231  w = 1/[σ2(Fo2) + (0.1307P)2 + 0.5522P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
6101 reflectionsΔρmax = 0.40 e Å3
396 parametersΔρmin = −0.52 e Å3
12 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

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)
H20.3247−0.07551.16320.065*
C30.2749 (3)−0.14779 (13)1.0499 (3)0.0633 (7)
H30.2074−0.16171.06580.076*
C40.3065 (3)−0.17779 (12)0.9680 (3)0.0605 (7)
H40.2622−0.21290.92910.073*
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)
H190.5493−0.08810.66900.072*
C200.5563 (3)−0.14547 (14)0.5363 (2)0.0620 (7)
C210.5237 (3)−0.20391 (16)0.4848 (3)0.0759 (9)
H210.4880−0.23270.51770.091*
C220.5437 (4)−0.21969 (19)0.3858 (3)0.0829 (10)
H220.5205−0.25860.35170.100*
C230.5977 (4)−0.17794 (19)0.3382 (3)0.0875 (12)
H230.6115−0.18870.27180.105*
C240.6317 (4)−0.12035 (17)0.3872 (3)0.0819 (10)
H240.6685−0.09230.35400.098*
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*
H26B0.7864−0.02740.50290.110*
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)
H2A0.6588−0.04661.09990.057*
N30.7217 (2)0.02594 (9)1.20320 (17)0.0485 (5)
N40.4772 (2)−0.14655 (10)0.7900 (2)0.0606 (6)
H4A0.4935−0.10870.81190.073*
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)

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, °)

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—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—O61.1 (4)
C2—C3—C4—C5−1.6 (4)C21—C20—C25—C240.7 (4)
C3—C4—C5—N12.7 (4)C19—C20—C25—C24179.7 (3)
C3—C4—C5—C18−175.0 (3)O6—C26—C27—O75.4 (7)
N1—C1—C6—O1163.9 (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—N2162.0 (2)C14—C15—O5—C16170.5 (6)
N3—C7—C8—C97.8 (4)C17—C16—O5—C1599.1 (12)
N3—C7—C8—C13−171.5 (2)O7—C27—O8—C2825.2 (11)
C13—C8—C9—C100.2 (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—C120.6 (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—C80.5 (4)C27—O8'—C28'—C29'146 (7)
C9—C8—C13—O3179.9 (2)C2—C1—N1—C5−0.8 (4)
C7—C8—C13—O3−0.8 (4)C6—C1—N1—C5179.0 (2)
C9—C8—C13—C12−0.3 (4)C4—C5—N1—C1−1.5 (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—O5−177.7 (3)C1—C6—N2—N3−176.90 (19)
N1—C5—C18—O2152.8 (3)C8—C7—N3—N2179.9 (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—N51.4 (5)
C4—C5—C18—N4148.0 (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—C216.6 (5)C18—N4—N5—C19177.1 (3)
C25—C20—C21—C22−1.0 (5)C12—C13—O3—C143.5 (4)
C19—C20—C21—C22179.9 (3)C8—C13—O3—C14−176.6 (2)
C20—C21—C22—C230.9 (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—C250.0 (5)C20—C25—O6—C26172.7 (3)
C23—C24—C25—O6178.3 (3)C27—C26—O6—C25−169.8 (3)

Hydrogen-bond geometry (Å, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2047).

References

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

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