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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m701–m702.
Published online 2008 April 23. doi:  10.1107/S160053680801074X
PMCID: PMC2961106

catena-Poly[[[bis­[4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)phenol-κ2 N 7,N 8]manganese(II)]-μ-naphthalene-1,4-dicarboxyl­ato-κ2 O 1:O 4] naphthalene-1,4-dicarboxylic acid hemisolvate monohydrate]

Abstract

The 1,4-dicarboxyl­ate dianions in the title compound, [Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O, bond to two 4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)phenol-chelated Mn atoms to form a chain that features the metal atom in an octa­hedral coordination geometry. Adjacent chains inter­act with the uncoordinated water mol­ecules to form a three-dimensional network. The naphthalene-1,4-dicarboxylic acid solvent mol­ecule, which is disordered about a centre of inversion, occupies the space within the network but is not bonded to the network. One NH group is disordered equally over two positions.

Related literature

There are several studies of (2-phenyl-1H-1,3,7,8,-tetra­azacyclo­penta­[l]phenanthrene-chelated manganese dicarb­oxyl­ates (see, for example, Li et al., 2008 [triangle]). The 4-hydr­oxy-substituted N-heterocycle forms an adduct with mangan­ese(II) terephthalate (see Che et al., 2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m701-scheme1.jpg

Experimental

Crystal data

  • [Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2O
  • M r = 1019.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m701-efi2.jpg
  • a = 48.398 (15) Å
  • b = 9.089 (2) Å
  • c = 20.598 (6) Å
  • β = 103.20 (1)°
  • V = 8821 (4) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.38 mm−1
  • T = 295 (2) K
  • 0.31 × 0.25 × 0.18 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.820, T max = 1.000 (expected range = 0.767–0.935)
  • 40785 measured reflections
  • 10014 independent reflections
  • 5868 reflections with I > 2σ(I)
  • R int = 0.084

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.170
  • S = 1.03
  • 10014 reflections
  • 717 parameters
  • 116 restraints
  • H-atom parameters constrained
  • Δρmax = 1.35 e Å−3
  • Δρmin = −0.42 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]) and OLEX (Dolomanov et al., 2003 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801074X/bx2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801074X/bx2132Isup2.hkl

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

Acknowledgments

The authors thank the Natural Science Foundation of Jilin Province (grant No. 20060516), the Doctoral Foundation of Jilin Normal University (grant No. 2006006), the Science and Technology Institute Foundation of Siping City (grant No. 2005016), the Subject and Base Construction Foundation of Jilin Normal University (grant No. 2006041) and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

There are manganese dicarboxylate adducts of complexes of 2-phenyl-1H-1,3,7,8-tetraazacyclopenta[l]phenanthrene (Li et al., 2008). The 4-hydroxy substituted ligand forms an adduct with manganese terephthalate (Che et al., 2006) that features a carboxylate-bridged chain motif. The title naphthalene-1,4-dicarboxylate adduct also adopts a layer motif. However, there is space between the chains that is large enough for a naphthalene-1,4-dicarboxylic acid molecule as well as a water molecule to fit in. Adjacent chains are linked by hydrogen bonds into a three-dimensional network.

Experimental

Manganese dichloride dihydrate (0.02 g, 0.1 mmol), naphthalene-1,4-dicarboxylic acid (0.02 g, 0.1 mmol), 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)phenol (0.03 g, 0.1 mmol) and water (15 ml) were heated in a 23 ml, Teflon-lined, stainless-steel Parr bomb at 408 K for 2 days. Crystals were obtained in 40% yield.

Refinement

The naphthalene-1,4-dicarboxylic acid is disordered over a center-of-inversion. The fused-ring portion was refined as a rigid naphthalene group of 1.39 Å sides; the occupancy is 0.5. The C–O distances were restrained to 1.25±0.01 Å and the Ccarboxyl–Caryl distances to 1.50±0.01 Å. Other restrained were applied to the carboxyl parts. The anisotropic displacement factors of the carbon and oxygen atoms were restrained to be nearly isotropic. The acid H atoms were arbitrarily placed on the carboxyl parts.

The carbon- and nitrogen-bound H atoms were placed in calculated positions [C–H 0.93, N–H 0.86, O–H 0.82 Å and Uiso(H) 1.2Ueq(C,N,O)], and were included in the refinement in the riding-model approximation. For one of the N-heterocycles, the amino –NH group is ordered whereas for the other, it is disordered. For the second N-heterocycle, hydrogen atoms of 0.5 occupancy were placed on the two nitrogen atoms. The water H-atoms were placed in chemically sensible positions on the basis of hydrogen bonds.

The final difference Fourier map had a large peak near H14, but this could not be modeled as a water molecule.

Figures

Fig. 1.
Thermal ellipsoid plot of Mn(C19H12N4O)2(C12H6O4).(C12H8O4)0.5.H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. The naphthalene-1,4-dicarboxylic acid is disordered about a center-of-inversion. ...
Fig. 2.
Chain structure of the manganese-naphthalene-1,4-dicarboxylate network as illustrated by OLEX (Dolomanov et al., 2003).

Crystal data

[Mn(C12H6O4)(C19H12N4O)2]·0.5C12H8O4·H2OF000 = 4200
Mr = 1019.87Dx = 1.536 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 24704 reflections
a = 48.398 (15) Åθ = 3.0–27.5º
b = 9.089 (2) ŵ = 0.38 mm1
c = 20.598 (6) ÅT = 295 (2) K
β = 103.20 (1)ºBlock, brown
V = 8821 (4) Å30.31 × 0.25 × 0.18 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer10014 independent reflections
Radiation source: fine-focus sealed tube5868 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.084
Detector resolution: 10 pixels mm-1θmax = 27.5º
T = 295(2) Kθmin = 3.0º
ω scansh = −62→62
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)k = −11→11
Tmin = 0.820, Tmax = 1.000l = −25→26
40785 measured 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)] = 0.060H-atom parameters constrained
wR(F2) = 0.170  w = 1/[σ2(Fo2) + (0.0782P)2 + 7.7802P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
10014 reflectionsΔρmax = 1.35 e Å3
717 parametersΔρmin = −0.42 e Å3
116 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Mn10.648562 (11)0.41289 (6)0.51035 (2)0.03142 (15)
O10.66266 (5)0.5844 (3)0.45399 (11)0.0379 (6)
O20.70748 (5)0.5903 (3)0.44417 (12)0.0468 (7)
O30.65765 (6)0.4702 (3)0.10116 (11)0.0487 (7)
O40.62358 (12)0.3337 (5)0.12178 (16)0.137 (2)
O50.80478 (5)−0.5497 (3)0.28409 (12)0.0431 (6)
H5O0.7975−0.57130.24530.052*
O60.39480 (6)0.0139 (4)0.56796 (15)0.0580 (8)
H6O0.38280.05380.53880.070*
O1W0.64402 (6)0.8246 (3)0.51341 (13)0.0585 (8)
H1W10.63810.78820.54400.070*
H1W20.65000.75800.49350.070*
N10.64987 (6)0.2597 (3)0.42332 (13)0.0329 (6)
N20.71343 (6)−0.0949 (3)0.35027 (13)0.0326 (6)
N30.74551 (6)−0.0806 (3)0.44653 (13)0.0323 (6)
H3N0.7608−0.09580.47650.039*
N40.68967 (6)0.2888 (3)0.53848 (13)0.0323 (6)
N50.60125 (6)0.4417 (3)0.47014 (14)0.0349 (7)
N60.50889 (6)0.2640 (4)0.49973 (15)0.0427 (8)
H6N0.49630.31270.47180.051*0.50
N70.52850 (6)0.1071 (3)0.58045 (15)0.0393 (7)
H7N0.53050.04220.61150.047*0.50
N80.62546 (6)0.2431 (3)0.56234 (13)0.0328 (6)
C10.68180 (7)0.5800 (4)0.42007 (15)0.0318 (7)
C20.67164 (7)0.5539 (4)0.34578 (15)0.0334 (8)
C30.68747 (8)0.4623 (4)0.31553 (18)0.0442 (9)
H30.70460.42570.34040.053*
C40.67855 (10)0.4222 (5)0.24807 (19)0.0520 (11)
H40.69040.36590.22820.062*
C50.65281 (9)0.4650 (4)0.21179 (17)0.0453 (10)
C60.63544 (8)0.5580 (4)0.24055 (17)0.0418 (9)
C70.60821 (10)0.6066 (6)0.2051 (2)0.0636 (14)
H70.60060.56990.16260.076*
C80.59313 (10)0.7050 (7)0.2321 (2)0.0763 (17)
H80.57500.73120.20870.092*
C90.60437 (9)0.7686 (6)0.2949 (2)0.0610 (13)
H90.59440.84140.31150.073*
C100.63004 (8)0.7224 (4)0.33118 (18)0.0446 (9)
H100.63750.76470.37260.053*
C110.64569 (8)0.6109 (4)0.30714 (16)0.0362 (8)
C120.64374 (11)0.4187 (5)0.13943 (18)0.0573 (12)
C130.63068 (8)0.2504 (4)0.36630 (17)0.0391 (8)
H130.61430.30710.36120.047*
C140.63352 (8)0.1611 (4)0.31385 (18)0.0443 (9)
H140.61950.15940.27450.053*
C150.65707 (7)0.0760 (4)0.32064 (16)0.0383 (8)
H150.65920.01400.28620.046*
C160.67804 (7)0.0824 (4)0.38000 (15)0.0309 (7)
C170.67358 (7)0.1766 (4)0.43056 (15)0.0277 (7)
C180.70380 (7)−0.0002 (4)0.39249 (15)0.0302 (7)
C190.73844 (7)−0.1426 (4)0.38480 (16)0.0319 (7)
C200.75594 (7)−0.2469 (4)0.35910 (15)0.0310 (7)
C210.74440 (8)−0.3234 (4)0.30051 (17)0.0375 (8)
H210.7256−0.30660.27870.045*
C220.76036 (7)−0.4235 (4)0.27433 (16)0.0363 (8)
H220.7523−0.47300.23500.044*
C230.78818 (7)−0.4505 (4)0.30626 (16)0.0326 (8)
C240.80001 (8)−0.3755 (4)0.36495 (17)0.0394 (9)
H240.8187−0.39320.38680.047*
C250.78397 (8)−0.2747 (4)0.39081 (17)0.0388 (8)
H250.7921−0.22490.43000.047*
C260.72353 (7)0.0112 (4)0.45189 (15)0.0305 (7)
C270.72016 (7)0.1082 (4)0.50390 (15)0.0303 (7)
C280.69495 (7)0.1906 (4)0.49268 (15)0.0289 (7)
C290.73988 (8)0.1291 (4)0.56409 (16)0.0368 (8)
H290.75670.07510.57340.044*
C300.73462 (8)0.2288 (4)0.60954 (17)0.0417 (9)
H300.74780.24480.64940.050*
C310.70901 (8)0.3062 (4)0.59476 (16)0.0370 (8)
H310.70540.37310.62600.044*
C320.58966 (8)0.5338 (4)0.42155 (17)0.0421 (9)
H320.60170.59400.40390.051*
C330.56062 (8)0.5453 (5)0.39549 (19)0.0472 (10)
H330.55360.60910.36030.057*
C340.54270 (8)0.4625 (4)0.42190 (18)0.0448 (9)
H340.52320.47030.40590.054*
C350.55415 (7)0.3645 (4)0.47394 (17)0.0352 (8)
C360.58368 (7)0.3551 (4)0.49587 (16)0.0308 (7)
C370.53799 (7)0.2739 (4)0.50782 (17)0.0375 (8)
C380.50402 (8)0.1628 (4)0.54421 (18)0.0390 (8)
C390.47567 (8)0.1240 (4)0.55059 (18)0.0398 (9)
C400.45204 (8)0.1852 (5)0.5075 (2)0.0466 (9)
H400.45460.25070.47460.056*
C410.42516 (8)0.1502 (4)0.51280 (19)0.0441 (9)
H410.40960.19180.48350.053*
C420.42095 (8)0.0535 (4)0.56145 (19)0.0418 (9)
C430.44413 (9)−0.0074 (5)0.6052 (2)0.0502 (10)
H430.4415−0.07190.63830.060*
C440.47111 (9)0.0282 (5)0.59918 (19)0.0482 (10)
H440.4866−0.01330.62850.058*
C450.54997 (7)0.1768 (4)0.55707 (16)0.0360 (8)
C460.58004 (7)0.1575 (4)0.57679 (16)0.0317 (7)
C470.59665 (7)0.2488 (4)0.54633 (15)0.0301 (7)
C480.59376 (8)0.0503 (4)0.62186 (18)0.0423 (9)
H480.5833−0.01480.64170.051*
C490.62277 (8)0.0435 (4)0.63611 (18)0.0422 (9)
H490.6324−0.02750.66530.051*
C500.63774 (8)0.1443 (4)0.60637 (17)0.0391 (9)
H500.65750.14160.61820.047*
O70.57620 (11)0.3027 (6)0.1777 (3)0.0515 (14)0.50
H7O0.58860.31120.15680.062*0.50
O80.54490 (15)0.4380 (7)0.1031 (3)0.0662 (18)0.50
O90.47578 (12)0.3147 (7)0.3757 (3)0.0619 (16)0.50
O100.46652 (12)0.0992 (7)0.3243 (3)0.0651 (17)0.50
H10O0.45750.07380.35170.078*0.50
C510.55115 (11)0.3657 (5)0.1545 (2)0.0409 (17)0.50
C520.53036 (7)0.3410 (4)0.19789 (16)0.0385 (17)0.50
C530.52596 (9)0.1961 (4)0.2146 (2)0.049 (2)0.50
H530.53520.12000.19810.059*0.50
C540.50771 (9)0.1650 (3)0.2560 (2)0.047 (2)0.50
H540.50480.06810.26720.056*0.50
C550.49387 (8)0.2788 (4)0.28073 (17)0.0461 (19)0.50
C560.49827 (9)0.4237 (4)0.2640 (2)0.042 (3)0.50
C570.51652 (9)0.4548 (3)0.22257 (19)0.041 (2)0.50
C580.52092 (14)0.5997 (4)0.2058 (3)0.044 (2)0.50
H580.53310.62050.17810.053*0.50
C590.50708 (19)0.7134 (3)0.2305 (4)0.047 (3)0.50
H590.51000.81040.21930.057*0.50
C600.48883 (19)0.6823 (4)0.2719 (4)0.068 (4)0.50
H600.47960.75840.28840.082*0.50
C610.48443 (14)0.5374 (5)0.2887 (3)0.057 (3)0.50
H610.47220.51660.31640.068*0.50
C620.47719 (9)0.2234 (7)0.3285 (3)0.050 (2)0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Mn10.0325 (3)0.0381 (3)0.0258 (2)0.0015 (2)0.0110 (2)−0.0006 (2)
O10.0453 (15)0.0431 (14)0.0294 (12)0.0010 (12)0.0171 (11)0.0011 (11)
O20.0342 (15)0.0710 (19)0.0338 (13)0.0000 (14)0.0048 (11)−0.0056 (13)
O30.0654 (19)0.0591 (17)0.0245 (12)0.0084 (15)0.0161 (12)0.0071 (12)
O40.217 (5)0.161 (4)0.0387 (18)−0.144 (4)0.040 (2)−0.035 (2)
O50.0398 (15)0.0600 (17)0.0289 (12)0.0147 (13)0.0063 (11)−0.0057 (12)
O60.0341 (15)0.080 (2)0.0612 (18)−0.0089 (15)0.0143 (13)0.0063 (17)
O1W0.063 (2)0.0632 (19)0.0460 (16)0.0125 (16)0.0062 (14)−0.0068 (14)
N10.0311 (15)0.0399 (16)0.0290 (14)0.0017 (13)0.0099 (12)−0.0012 (13)
N20.0337 (15)0.0388 (16)0.0262 (13)0.0026 (13)0.0087 (12)−0.0015 (13)
N30.0321 (15)0.0394 (16)0.0254 (13)0.0046 (13)0.0063 (11)−0.0030 (13)
N40.0352 (16)0.0368 (16)0.0260 (13)0.0003 (13)0.0092 (12)−0.0023 (12)
N50.0364 (16)0.0382 (16)0.0323 (14)0.0028 (13)0.0124 (13)0.0040 (13)
N60.0330 (17)0.0523 (19)0.0438 (17)−0.0035 (15)0.0109 (14)0.0065 (16)
N70.0322 (16)0.0495 (18)0.0385 (16)−0.0004 (14)0.0128 (13)0.0016 (14)
N80.0298 (15)0.0368 (15)0.0325 (14)0.0026 (13)0.0084 (12)0.0012 (13)
C10.0367 (19)0.0358 (18)0.0249 (15)0.0006 (16)0.0112 (14)0.0000 (15)
C20.0381 (19)0.0400 (19)0.0236 (15)−0.0060 (16)0.0100 (14)0.0004 (14)
C30.045 (2)0.056 (2)0.0338 (18)0.0049 (19)0.0142 (17)0.0013 (18)
C40.071 (3)0.056 (3)0.0351 (19)0.001 (2)0.025 (2)−0.0081 (19)
C50.066 (3)0.047 (2)0.0250 (17)−0.019 (2)0.0147 (18)−0.0020 (17)
C60.046 (2)0.054 (2)0.0257 (16)−0.0174 (19)0.0090 (16)0.0095 (16)
C70.053 (3)0.105 (4)0.0291 (19)−0.024 (3)0.0025 (19)0.016 (2)
C80.040 (3)0.137 (5)0.052 (3)0.002 (3)0.010 (2)0.044 (3)
C90.052 (3)0.085 (3)0.052 (2)0.020 (2)0.023 (2)0.029 (2)
C100.046 (2)0.053 (2)0.0374 (19)0.0059 (19)0.0164 (17)0.0095 (18)
C110.040 (2)0.045 (2)0.0260 (16)−0.0073 (17)0.0123 (15)0.0060 (15)
C120.091 (4)0.056 (3)0.0261 (18)−0.027 (3)0.016 (2)−0.0040 (18)
C130.0334 (19)0.048 (2)0.0349 (18)0.0104 (17)0.0046 (15)−0.0018 (17)
C140.040 (2)0.057 (2)0.0319 (18)0.0058 (19)0.0005 (16)−0.0063 (18)
C150.037 (2)0.050 (2)0.0259 (16)0.0047 (17)0.0036 (14)−0.0065 (16)
C160.0302 (17)0.0365 (18)0.0267 (15)0.0009 (15)0.0079 (13)0.0009 (15)
C170.0292 (17)0.0319 (17)0.0240 (15)−0.0016 (14)0.0101 (13)0.0026 (14)
C180.0328 (18)0.0345 (18)0.0242 (15)−0.0004 (15)0.0081 (13)−0.0003 (14)
C190.0349 (19)0.0378 (18)0.0245 (15)−0.0003 (16)0.0100 (14)0.0001 (14)
C200.0345 (18)0.0346 (18)0.0254 (15)−0.0001 (15)0.0102 (14)0.0000 (14)
C210.0333 (19)0.046 (2)0.0328 (17)0.0057 (17)0.0059 (15)−0.0018 (16)
C220.038 (2)0.044 (2)0.0261 (16)0.0038 (17)0.0054 (14)−0.0039 (15)
C230.0329 (18)0.0381 (19)0.0286 (16)0.0056 (15)0.0105 (14)0.0018 (15)
C240.0311 (19)0.052 (2)0.0328 (18)0.0045 (17)0.0033 (15)−0.0039 (17)
C250.037 (2)0.048 (2)0.0299 (17)0.0024 (17)0.0034 (15)−0.0071 (16)
C260.0332 (18)0.0330 (17)0.0268 (15)0.0008 (15)0.0100 (14)0.0010 (14)
C270.0302 (17)0.0366 (18)0.0268 (15)−0.0007 (15)0.0120 (13)0.0013 (14)
C280.0318 (18)0.0303 (17)0.0262 (15)−0.0040 (14)0.0101 (13)0.0001 (14)
C290.0351 (19)0.046 (2)0.0290 (16)0.0058 (16)0.0063 (15)−0.0019 (16)
C300.040 (2)0.054 (2)0.0295 (17)−0.0006 (19)0.0056 (16)−0.0060 (17)
C310.039 (2)0.043 (2)0.0289 (17)−0.0010 (17)0.0090 (15)−0.0066 (16)
C320.042 (2)0.049 (2)0.0361 (18)−0.0013 (18)0.0110 (16)0.0100 (18)
C330.044 (2)0.054 (2)0.041 (2)0.0009 (19)0.0049 (18)0.0148 (19)
C340.037 (2)0.055 (2)0.039 (2)0.0008 (19)0.0008 (16)0.0106 (19)
C350.0342 (19)0.042 (2)0.0307 (17)−0.0010 (16)0.0091 (15)0.0025 (16)
C360.0323 (18)0.0346 (18)0.0274 (16)−0.0006 (15)0.0105 (14)−0.0029 (14)
C370.0311 (19)0.050 (2)0.0309 (17)−0.0002 (17)0.0063 (15)0.0032 (17)
C380.036 (2)0.045 (2)0.0395 (19)−0.0020 (17)0.0160 (16)0.0007 (17)
C390.037 (2)0.046 (2)0.0386 (19)−0.0034 (17)0.0139 (16)−0.0045 (17)
C400.043 (2)0.052 (2)0.048 (2)−0.0024 (19)0.0168 (18)0.0041 (19)
C410.039 (2)0.051 (2)0.043 (2)−0.0001 (18)0.0112 (17)−0.0025 (19)
C420.035 (2)0.050 (2)0.043 (2)−0.0077 (17)0.0151 (16)−0.0104 (18)
C430.046 (2)0.062 (3)0.046 (2)−0.007 (2)0.0171 (19)0.006 (2)
C440.041 (2)0.060 (3)0.043 (2)0.001 (2)0.0106 (17)0.010 (2)
C450.035 (2)0.044 (2)0.0308 (17)−0.0026 (17)0.0115 (15)0.0003 (16)
C460.0331 (19)0.0352 (18)0.0270 (16)0.0029 (15)0.0071 (14)−0.0005 (15)
C470.0318 (18)0.0328 (17)0.0262 (15)−0.0006 (15)0.0076 (14)−0.0032 (14)
C480.044 (2)0.045 (2)0.0374 (19)0.0030 (18)0.0094 (17)0.0073 (17)
C490.045 (2)0.043 (2)0.0391 (19)0.0104 (18)0.0096 (17)0.0120 (17)
C500.037 (2)0.046 (2)0.0351 (18)0.0063 (17)0.0103 (16)0.0060 (17)
O70.048 (3)0.060 (3)0.053 (3)−0.014 (3)0.025 (3)0.002 (3)
O80.092 (5)0.072 (4)0.044 (3)0.014 (3)0.033 (3)0.016 (3)
O90.052 (3)0.088 (4)0.050 (3)0.004 (3)0.021 (3)0.023 (3)
O100.057 (4)0.074 (4)0.068 (4)−0.012 (3)0.023 (3)0.030 (3)
C510.044 (4)0.043 (4)0.039 (4)−0.007 (3)0.016 (3)−0.009 (3)
C520.039 (4)0.041 (4)0.036 (3)−0.005 (3)0.010 (3)−0.001 (3)
C530.072 (5)0.042 (4)0.033 (4)−0.005 (4)0.013 (4)0.000 (4)
C540.064 (7)0.039 (3)0.033 (4)−0.013 (3)0.004 (4)0.002 (4)
C550.039 (4)0.054 (4)0.044 (4)0.002 (4)0.006 (3)0.022 (4)
C560.046 (4)0.045 (4)0.029 (6)0.003 (5)−0.008 (4)0.010 (3)
C570.045 (5)0.041 (5)0.031 (4)−0.002 (4)−0.002 (4)0.005 (4)
C580.041 (5)0.047 (5)0.045 (4)−0.004 (4)0.008 (4)−0.015 (4)
C590.065 (6)0.027 (4)0.050 (6)−0.002 (4)0.014 (5)−0.001 (4)
C600.062 (7)0.075 (6)0.072 (8)0.011 (6)0.023 (6)−0.009 (6)
C610.036 (5)0.080 (7)0.057 (6)0.003 (5)0.018 (4)0.012 (5)
C620.036 (4)0.061 (5)0.055 (5)−0.003 (4)0.011 (4)0.014 (4)

Geometric parameters (Å, °)

Mn1—O12.146 (2)C21—H210.9300
Mn1—O3i2.108 (2)C22—C231.379 (5)
Mn1—N12.282 (3)C22—H220.9300
Mn1—N42.245 (3)C23—C241.392 (5)
Mn1—N52.265 (3)C24—C251.384 (5)
Mn1—N82.307 (3)C24—H240.9300
O1—C11.282 (4)C25—H250.9300
O2—C11.232 (4)C26—C271.425 (4)
O3—C121.239 (5)C27—C291.394 (4)
O3—Mn1ii2.108 (2)C27—C281.405 (5)
O4—C121.232 (5)C29—C301.368 (5)
O5—C231.354 (4)C29—H290.9300
O5—H5O0.8200C30—C311.397 (5)
O6—C421.352 (4)C30—H300.9300
O6—H6O0.8200C31—H310.9300
O1W—H1W10.8201C32—C331.389 (5)
O1W—H1W20.8200C32—H320.9300
N1—C131.323 (4)C33—C341.352 (5)
N1—C171.353 (4)C33—H330.9300
N2—C191.329 (4)C34—C351.407 (5)
N2—C181.379 (4)C34—H340.9300
N3—C191.361 (4)C35—C361.400 (5)
N3—C261.376 (4)C35—C371.423 (5)
N3—H3N0.8600C36—C471.453 (5)
N4—C311.323 (4)C37—C451.369 (5)
N4—C281.364 (4)C38—C391.452 (5)
N5—C321.327 (4)C39—C441.382 (5)
N5—C361.352 (4)C39—C401.394 (5)
N6—C381.356 (5)C40—C411.368 (5)
N6—C371.383 (4)C40—H400.9300
N6—H6N0.8600C41—C421.383 (5)
N7—C381.347 (5)C41—H410.9300
N7—C451.393 (4)C42—C431.384 (5)
N7—H7N0.8600C43—C441.378 (5)
N8—C501.318 (4)C43—H430.9300
N8—C471.359 (4)C44—H440.9300
C1—C21.515 (4)C45—C461.430 (5)
C2—C31.374 (5)C46—C471.400 (5)
C2—C111.422 (5)C46—C481.403 (5)
C3—C41.406 (5)C48—C491.369 (5)
C3—H30.9300C48—H480.9300
C4—C51.355 (6)C49—C501.394 (5)
C4—H40.9300C49—H490.9300
C5—C61.414 (6)C50—H500.9300
C5—C121.514 (5)O7—C511.327 (6)
C6—C71.423 (6)O7—H7O0.8201
C6—C111.431 (5)O8—C511.223 (6)
C7—C81.351 (7)O9—C621.291 (7)
C7—H70.9300O10—C621.236 (7)
C8—C91.409 (7)O10—H10O0.8198
C8—H80.9300C51—C521.507 (5)
C9—C101.362 (5)C52—C531.3900
C9—H90.9300C52—C571.3900
C10—C111.420 (5)C53—C541.3900
C10—H100.9300C53—H530.9300
C13—C141.383 (5)C54—C551.3900
C13—H130.9300C54—H540.9300
C14—C151.358 (5)C55—C561.3900
C14—H140.9300C55—C621.496 (5)
C15—C161.401 (4)C56—C571.3900
C15—H150.9300C56—C611.3900
C16—C171.402 (4)C57—C581.3900
C16—C181.427 (5)C58—C591.3900
C17—C281.455 (4)C58—H580.9300
C18—C261.373 (4)C59—C601.3900
C19—C201.449 (5)C59—H590.9300
C20—C251.388 (5)C60—C611.3900
C20—C211.394 (5)C60—H600.9300
C21—C221.381 (5)C61—H610.9300
O1—Mn1—O3i95.0 (1)C24—C25—H25119.5
O1—Mn1—N187.1 (1)C20—C25—H25119.5
O1—Mn1—N497.6 (1)C18—C26—N3106.0 (3)
O1—Mn1—N597.9 (1)C18—C26—C27122.7 (3)
O1—Mn1—N8169.9 (1)N3—C26—C27131.2 (3)
O3i—Mn1—N1165.2 (1)C29—C27—C28117.8 (3)
O3i—Mn1—N491.8 (1)C29—C27—C26125.4 (3)
O3i—Mn1—N5104.8 (1)C28—C27—C26116.8 (3)
O3i—Mn1—N887.1 (1)N4—C28—C27121.8 (3)
N1—Mn1—N473.4 (1)N4—C28—C17117.2 (3)
N1—Mn1—N589.5 (1)C27—C28—C17120.9 (3)
N1—Mn1—N893.4 (1)C30—C29—C27120.1 (3)
N4—Mn1—N5156.2 (1)C30—C29—H29119.9
N4—Mn1—N892.2 (1)C27—C29—H29119.9
N5—Mn1—N872.0 (1)C29—C30—C31118.6 (3)
C1—O1—Mn1129.1 (2)C29—C30—H30120.7
C12—O3—Mn1ii136.2 (3)C31—C30—H30120.7
C23—O5—H5O109.5N4—C31—C30123.1 (3)
C42—O6—H6O109.5N4—C31—H31118.5
H1W1—O1W—H1W2108.2C30—C31—H31118.5
C13—N1—C17117.9 (3)N5—C32—C33123.7 (4)
C13—N1—Mn1126.6 (2)N5—C32—H32118.1
C17—N1—Mn1115.4 (2)C33—C32—H32118.1
C19—N2—C18105.3 (3)C34—C33—C32119.2 (4)
C19—N3—C26107.0 (3)C34—C33—H33120.4
C19—N3—H3N126.5C32—C33—H33120.4
C26—N3—H3N126.5C33—C34—C35118.8 (4)
C31—N4—C28118.5 (3)C33—C34—H34120.6
C31—N4—Mn1125.0 (2)C35—C34—H34120.6
C28—N4—Mn1116.4 (2)C36—C35—C34118.7 (3)
C32—N5—C36117.9 (3)C36—C35—C37116.2 (3)
C32—N5—Mn1124.5 (2)C34—C35—C37125.1 (3)
C36—N5—Mn1117.6 (2)N5—C36—C35121.7 (3)
C38—N6—C37107.0 (3)N5—C36—C47117.4 (3)
C38—N6—H6N126.5C35—C36—C47120.9 (3)
C37—N6—H6N126.5C45—C37—N6107.1 (3)
C38—N7—C45105.6 (3)C45—C37—C35123.3 (3)
C38—N7—H7N127.2N6—C37—C35129.6 (3)
C45—N7—H7N127.2N7—C38—N6111.3 (3)
C50—N8—C47118.0 (3)N7—C38—C39126.1 (3)
C50—N8—Mn1125.8 (2)N6—C38—C39122.7 (3)
C47—N8—Mn1116.2 (2)C44—C39—C40118.0 (4)
O2—C1—O1124.5 (3)C44—C39—C38122.0 (3)
O2—C1—C2118.9 (3)C40—C39—C38120.0 (3)
O1—C1—C2116.6 (3)C41—C40—C39120.9 (4)
C3—C2—C11118.7 (3)C41—C40—H40119.6
C3—C2—C1117.8 (3)C39—C40—H40119.6
C11—C2—C1123.4 (3)C40—C41—C42120.4 (4)
C2—C3—C4121.9 (4)C40—C41—H41119.8
C2—C3—H3119.1C42—C41—H41119.8
C4—C3—H3119.1O6—C42—C41122.5 (4)
C5—C4—C3120.4 (4)O6—C42—C43117.8 (4)
C5—C4—H4119.8C41—C42—C43119.7 (4)
C3—C4—H4119.8C44—C43—C42119.4 (4)
C4—C5—C6120.0 (3)C44—C43—H43120.3
C4—C5—C12119.1 (4)C42—C43—H43120.3
C6—C5—C12120.8 (4)C43—C44—C39121.6 (4)
C5—C6—C7122.7 (4)C43—C44—H44119.2
C5—C6—C11119.5 (4)C39—C44—H44119.2
C7—C6—C11117.7 (4)C37—C45—N7109.1 (3)
C8—C7—C6121.3 (4)C37—C45—C46121.4 (3)
C8—C7—H7119.4N7—C45—C46129.6 (3)
C6—C7—H7119.4C47—C46—C48118.3 (3)
C7—C8—C9121.2 (4)C47—C46—C45116.8 (3)
C7—C8—H8119.4C48—C46—C45124.8 (3)
C9—C8—H8119.4N8—C47—C46122.1 (3)
C10—C9—C8119.3 (5)N8—C47—C36116.8 (3)
C10—C9—H9120.3C46—C47—C36121.1 (3)
C8—C9—H9120.3C49—C48—C46118.7 (4)
C9—C10—C11121.4 (4)C49—C48—H48120.6
C9—C10—H10119.3C46—C48—H48120.6
C11—C10—H10119.3C48—C49—C50119.1 (3)
C10—C11—C2122.5 (3)C48—C49—H49120.4
C10—C11—C6118.6 (3)C50—C49—H49120.4
C2—C11—C6118.9 (3)N8—C50—C49123.5 (4)
O4—C12—O3123.9 (4)N8—C50—H50118.2
O4—C12—C5119.8 (4)C49—C50—H50118.2
O3—C12—C5116.3 (4)C51—O7—H7O119.4
N1—C13—C14123.8 (3)C62—O10—H10O119.1
N1—C13—H13118.1O8—C51—O7124.6 (6)
C14—C13—H13118.1O8—C51—C52121.8 (5)
C15—C14—C13119.0 (3)O7—C51—C52113.7 (4)
C15—C14—H14120.5C53—C52—C57120.0
C13—C14—H14120.5C53—C52—C51116.7 (3)
C14—C15—C16119.3 (3)C57—C52—C51123.3 (3)
C14—C15—H15120.3C52—C53—C54120.0
C16—C15—H15120.3C52—C53—H53120.0
C17—C16—C15118.0 (3)C54—C53—H53120.0
C17—C16—C18117.6 (3)C55—C54—C53120.0
C15—C16—C18124.4 (3)C55—C54—H54120.0
N1—C17—C16122.0 (3)C53—C54—H54120.0
N1—C17—C28117.6 (3)C54—C55—C56120.0
C16—C17—C28120.5 (3)C54—C55—C62111.6 (3)
C26—C18—N2110.0 (3)C56—C55—C62128.2 (3)
C26—C18—C16121.5 (3)C55—C56—C57120.0
N2—C18—C16128.5 (3)C55—C56—C61120.0
N2—C19—N3111.6 (3)C57—C56—C61120.0
N2—C19—C20123.7 (3)C58—C57—C56120.0
N3—C19—C20124.7 (3)C58—C57—C52120.0
C25—C20—C21118.2 (3)C56—C57—C52120.0
C25—C20—C19122.5 (3)C57—C58—C59120.0
C21—C20—C19119.3 (3)C57—C58—H58120.0
C22—C21—C20121.2 (3)C59—C58—H58120.0
C22—C21—H21119.4C58—C59—C60120.0
C20—C21—H21119.4C58—C59—H59120.0
C23—C22—C21120.2 (3)C60—C59—H59120.0
C23—C22—H22119.9C61—C60—C59120.0
C21—C22—H22119.9C61—C60—H60120.0
O5—C23—C22123.2 (3)C59—C60—H60120.0
O5—C23—C24117.4 (3)C60—C61—C56120.0
C22—C23—C24119.4 (3)C60—C61—H61120.0
C25—C24—C23120.2 (3)C56—C61—H61120.0
C25—C24—H24119.9O10—C62—O9123.2 (6)
C23—C24—H24119.9O10—C62—C55122.7 (6)
C24—C25—C20120.9 (3)O9—C62—C55114.1 (5)
O3i—Mn1—O1—C1122.4 (3)C19—N3—C26—C180.4 (4)
N4—Mn1—O1—C130.0 (3)C19—N3—C26—C27−176.7 (3)
N5—Mn1—O1—C1−131.9 (3)C18—C26—C27—C29−177.3 (3)
N1—Mn1—O1—C1−42.8 (3)N3—C26—C27—C29−0.6 (6)
N8—Mn1—O1—C1−136.0 (5)C18—C26—C27—C281.8 (5)
O3i—Mn1—N1—C13−177.0 (4)N3—C26—C27—C28178.4 (3)
O1—Mn1—N1—C13−78.7 (3)C31—N4—C28—C270.1 (5)
N4—Mn1—N1—C13−177.5 (3)Mn1—N4—C28—C27178.8 (2)
N5—Mn1—N1—C1319.3 (3)C31—N4—C28—C17−178.5 (3)
N8—Mn1—N1—C1391.2 (3)Mn1—N4—C28—C170.2 (4)
O3i—Mn1—N1—C17−0.7 (6)C29—C27—C28—N40.3 (5)
O1—Mn1—N1—C1797.6 (2)C26—C27—C28—N4−178.8 (3)
N4—Mn1—N1—C17−1.2 (2)C29—C27—C28—C17178.9 (3)
N5—Mn1—N1—C17−164.4 (2)C26—C27—C28—C17−0.2 (4)
N8—Mn1—N1—C17−92.5 (2)N1—C17—C28—N4−1.3 (4)
O3i—Mn1—N4—C31−0.8 (3)C16—C17—C28—N4177.4 (3)
O1—Mn1—N4—C3194.4 (3)N1—C17—C28—C27−179.9 (3)
N5—Mn1—N4—C31−135.3 (3)C16—C17—C28—C27−1.3 (5)
N1—Mn1—N4—C31179.1 (3)C28—C27—C29—C30−1.0 (5)
N8—Mn1—N4—C31−88.0 (3)C26—C27—C29—C30178.0 (3)
O3i—Mn1—N4—C28−179.4 (2)C27—C29—C30—C311.2 (6)
O1—Mn1—N4—C28−84.1 (2)C28—N4—C31—C300.1 (5)
N5—Mn1—N4—C2846.1 (4)Mn1—N4—C31—C30−178.5 (3)
N1—Mn1—N4—C280.5 (2)C29—C30—C31—N4−0.7 (6)
N8—Mn1—N4—C2893.4 (2)C36—N5—C32—C33−0.5 (6)
O3i—Mn1—N5—C32102.6 (3)Mn1—N5—C32—C33177.0 (3)
O1—Mn1—N5—C325.3 (3)N5—C32—C33—C342.3 (6)
N4—Mn1—N5—C32−124.9 (3)C32—C33—C34—C35−1.6 (6)
N1—Mn1—N5—C32−81.7 (3)C33—C34—C35—C36−0.8 (6)
N8—Mn1—N5—C32−175.4 (3)C33—C34—C35—C37178.1 (4)
O3i—Mn1—N5—C36−79.9 (3)C32—N5—C36—C35−2.0 (5)
O1—Mn1—N5—C36−177.2 (2)Mn1—N5—C36—C35−179.7 (3)
N4—Mn1—N5—C3652.6 (4)C32—N5—C36—C47176.5 (3)
N1—Mn1—N5—C3695.8 (2)Mn1—N5—C36—C47−1.1 (4)
N8—Mn1—N5—C362.0 (2)C34—C35—C36—N52.7 (5)
O3i—Mn1—N8—C50−75.1 (3)C37—C35—C36—N5−176.3 (3)
O1—Mn1—N8—C50−177.4 (5)C34—C35—C36—C47−175.9 (3)
N4—Mn1—N8—C5016.5 (3)C37—C35—C36—C475.2 (5)
N5—Mn1—N8—C50178.3 (3)C38—N6—C37—C450.4 (4)
N1—Mn1—N8—C5090.0 (3)C38—N6—C37—C35−179.4 (4)
O3i—Mn1—N8—C47103.7 (2)C36—C35—C37—C45−3.0 (5)
O1—Mn1—N8—C471.5 (7)C34—C35—C37—C45178.1 (4)
N4—Mn1—N8—C47−164.6 (2)C36—C35—C37—N6176.8 (4)
N5—Mn1—N8—C47−2.8 (2)C34—C35—C37—N6−2.1 (7)
N1—Mn1—N8—C47−91.1 (2)C45—N7—C38—N6−0.3 (4)
Mn1—O1—C1—O2−80.7 (4)C45—N7—C38—C39−179.8 (4)
Mn1—O1—C1—C296.7 (3)C37—N6—C38—N7−0.1 (4)
O2—C1—C2—C337.7 (5)C37—N6—C38—C39179.4 (3)
O1—C1—C2—C3−139.9 (4)N7—C38—C39—C443.9 (6)
O2—C1—C2—C11−146.9 (4)N6—C38—C39—C44−175.5 (4)
O1—C1—C2—C1135.6 (5)N7—C38—C39—C40−176.9 (4)
C11—C2—C3—C4−0.8 (6)N6—C38—C39—C403.7 (6)
C1—C2—C3—C4174.8 (3)C44—C39—C40—C41−0.6 (6)
C2—C3—C4—C5−4.7 (6)C38—C39—C40—C41−179.8 (4)
C3—C4—C5—C63.8 (6)C39—C40—C41—C420.2 (6)
C3—C4—C5—C12−179.4 (4)C40—C41—C42—O6−178.9 (4)
C4—C5—C6—C7−179.9 (4)C40—C41—C42—C430.4 (6)
C12—C5—C6—C73.4 (6)O6—C42—C43—C44178.7 (4)
C4—C5—C6—C112.4 (6)C41—C42—C43—C44−0.6 (6)
C12—C5—C6—C11−174.3 (3)C42—C43—C44—C390.2 (7)
C5—C6—C7—C8−174.5 (4)C40—C39—C44—C430.3 (6)
C11—C6—C7—C83.3 (6)C38—C39—C44—C43179.6 (4)
C6—C7—C8—C93.1 (7)N6—C37—C45—N7−0.7 (4)
C7—C8—C9—C10−4.7 (7)C35—C37—C45—N7179.2 (3)
C8—C9—C10—C11−0.3 (6)N6—C37—C45—C46178.6 (3)
C9—C10—C11—C2−175.8 (4)C35—C37—C45—C46−1.6 (6)
C9—C10—C11—C66.6 (5)C38—N7—C45—C370.6 (4)
C3—C2—C11—C10−170.6 (3)C38—N7—C45—C46−178.5 (4)
C1—C2—C11—C1014.0 (5)C37—C45—C46—C473.9 (5)
C3—C2—C11—C66.9 (5)N7—C45—C46—C47−177.1 (3)
C1—C2—C11—C6−168.4 (3)C37—C45—C46—C48−173.3 (3)
C5—C6—C11—C10169.9 (3)N7—C45—C46—C485.8 (6)
C7—C6—C11—C10−8.0 (5)C50—N8—C47—C462.4 (5)
C5—C6—C11—C2−7.8 (5)Mn1—N8—C47—C46−176.6 (2)
C7—C6—C11—C2174.4 (3)C50—N8—C47—C36−177.8 (3)
Mn1ii—O3—C12—O453.9 (8)Mn1—N8—C47—C363.3 (4)
Mn1ii—O3—C12—C5−126.4 (4)C48—C46—C47—N8−4.4 (5)
C4—C5—C12—O4113.9 (6)C45—C46—C47—N8178.2 (3)
C6—C5—C12—O4−69.4 (7)C48—C46—C47—C36175.8 (3)
C4—C5—C12—O3−65.9 (6)C45—C46—C47—C36−1.6 (5)
C6—C5—C12—O3110.9 (5)N5—C36—C47—N8−1.5 (4)
C17—N1—C13—C14−0.2 (6)C35—C36—C47—N8177.1 (3)
Mn1—N1—C13—C14176.1 (3)N5—C36—C47—C46178.4 (3)
N1—C13—C14—C150.8 (6)C35—C36—C47—C46−3.0 (5)
C13—C14—C15—C16−1.0 (6)C47—C46—C48—C492.6 (5)
C14—C15—C16—C170.6 (5)C45—C46—C48—C49179.7 (4)
C14—C15—C16—C18−179.1 (3)C46—C48—C49—C501.0 (6)
C13—N1—C17—C16−0.3 (5)C47—N8—C50—C491.5 (5)
Mn1—N1—C17—C16−176.9 (2)Mn1—N8—C50—C49−179.7 (3)
C13—N1—C17—C28178.3 (3)C48—C49—C50—N8−3.2 (6)
Mn1—N1—C17—C281.7 (4)O8—C51—C52—C53127.7 (3)
C15—C16—C17—N10.1 (5)O7—C51—C52—C53−52.4 (3)
C18—C16—C17—N1179.8 (3)O8—C51—C52—C57−54.2 (3)
C15—C16—C17—C28−178.5 (3)O7—C51—C52—C57125.7 (3)
C18—C16—C17—C281.2 (5)C57—C52—C53—C540.0
C19—N2—C18—C261.5 (4)C51—C52—C53—C54178.2 (2)
C19—N2—C18—C16179.4 (3)C52—C53—C54—C550.0
C17—C16—C18—C260.3 (5)C53—C54—C55—C560.0
C15—C16—C18—C26180.0 (3)C53—C54—C55—C62−175.3 (2)
C17—C16—C18—N2−177.4 (3)C54—C55—C56—C570.0
C15—C16—C18—N22.3 (6)C62—C55—C56—C57174.4 (2)
C18—N2—C19—N3−1.2 (4)C54—C55—C56—C61180.0
C18—N2—C19—C20179.2 (3)C62—C55—C56—C61−5.6 (2)
C26—N3—C19—N20.6 (4)C55—C56—C57—C58180.0
C26—N3—C19—C20−179.9 (3)C61—C56—C57—C580.0
N2—C19—C20—C25168.0 (3)C55—C56—C57—C520.0
N3—C19—C20—C25−11.5 (5)C61—C56—C57—C52180.0
N2—C19—C20—C21−12.3 (5)C53—C52—C57—C58180.0
N3—C19—C20—C21168.2 (3)C51—C52—C57—C582.0 (2)
C25—C20—C21—C22−0.4 (5)C53—C52—C57—C560.0
C19—C20—C21—C22179.9 (3)C51—C52—C57—C56−178.0 (2)
C20—C21—C22—C230.4 (6)C56—C57—C58—C590.0
C21—C22—C23—O5178.4 (3)C52—C57—C58—C59180.0
C21—C22—C23—C24−0.2 (5)C57—C58—C59—C600.0
O5—C23—C24—C25−178.8 (3)C58—C59—C60—C610.0
C22—C23—C24—C25−0.2 (6)C59—C60—C61—C560.0
C23—C24—C25—C200.2 (6)C55—C56—C61—C60180.0
C21—C20—C25—C240.0 (5)C57—C56—C61—C600.0
C19—C20—C25—C24179.8 (3)C54—C55—C62—O10−30.3 (3)
N2—C18—C26—N3−1.1 (4)C56—C55—C62—O10154.9 (3)
C16—C18—C26—N3−179.2 (3)C54—C55—C62—O9147.5 (3)
N2—C18—C26—C27176.2 (3)C56—C55—C62—O9−27.3 (3)
C16—C18—C26—C27−1.8 (5)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5O···N2iii0.821.932.737 (4)168
O6—H6O···O1Wiv0.821.852.656 (4)168
N3—H3N···O2v0.861.972.813 (4)166
N6—H6N···O90.862.002.728 (6)142
N7—H7N···O10vi0.861.832.685 (6)178
O1W—H1W2···O10.821.942.754 (4)173
O1W—H1W1···O4i0.822.193.007 (6)173

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2132).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Che, G.-B., Lin, X.-F. & Liu, C.-B. (2006). Acta Cryst. E62, m1456–m1458.
  • Dolomanov, O. V., Blake, A. J., Champness, N. R. & Schröder, M. (2003). J. Appl. Cryst.36, 1283–1284.
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Li, H.-D., Liu, Y., Xu, M.-L. & Ng, S. W. (2008). Acta Cryst. E64, m704–m705. [PMC free article] [PubMed]
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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