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Acta Cryst. (2007). E63, m2150    [ doi:10.1107/S1600536807033752 ]

(Adamantane-1,3-dicarboxylato-[kappa]O)aquabis(1,10-phenanthroline-[kappa]2N,N')cobalt(II) tetrahydrate

G.-L. Zhao, X. Shi and S. W. Ng

Abstract top

The CoII atom in the racemic title compound, [Co(C12H14O4)(C12H8N2)2(H2O)]·4H2O, is chelated by two N-heterocycles; it is also linked datively to a water molecule and covalently to a single O atom of the dicarboxylate dianion to yield a cis-CoO2N4 octahedral geometry. A plausible O-H...O hydrogen-bonding scheme results in the component species being linked into a chain.

Comment top

The crystal structures of an enormous number of metal(II) dicarboxylates have been reported (CSD Version 5.28, May 2007; Allen, 2002). However, there is no example of a metal 1,3-adamantanedicarboxylate; the crystal structure of the dicarboxylic acid itself has been known for some time (Glidewell & Ferguson, 1996).

The cobalt(II) atom in the title compound, (I), (Fig. 1), is chelated by two N-heterocycles; it is also linked datively to a water molecule and covalently to a single O atom of the dicarboxylate dianion in an all-cis octahedral geometry (Table 1). The mononuclear complex exists as as a zwitterion (i.e. formal Co+ and free –CO2- carboxyate anion in the same molecule). The component species of (I) are linked into a chain by ay of O—H···O interactions (Table 2).

Related literature top

There are no examples of metal derivatives of this dicarboxylic acid according to the Cambridge Structural Database (Version 5.28; May 2007; Allen, 2002). For the structure of the free acid, see: Glidewell & Ferguson (1996).

Experimental top

Cobalt diacetate tetrahydrate (1 mmol), 1,3-adamantanedicarboxylic acid (1 mmol) and 1,10-phenanthroline (2 mmol) were dissolved in ethanol (50 ml). The solution was set aside for the growth of the yellow plates of (I), which were isolated after a week.

Refinement top

The carbon-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å), and refined as riding with Uiso(H) = 1.2Ueq(C). The H atoms of water were placed (O—H = 0.85 Å) to generate a chemically plausible hydrogen bonding scheme and refined as riding with Uiso(H) = 1.2Ueq(O). In the resulting scheme, which should be regarded as tentative, the O4w water molecule forms only one hydrogen bond.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of (I); displacement ellipsoids are drawn at the 50% probabilty level and hydrogen atoms as spheres of arbitrary radius.
(Adamantane-1,3-dicarboxylato-κO)aquabis(1,10-phenanthroline-\ κ2N,N')cobalt(II) tetrahydrate top
Crystal data top
[Co(C12H14O4)(C12H8N2)2(H2O)]·4H2OZ = 2
Mr = 731.65F(000) = 766
Triclinic, P1Dx = 1.429 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.9902 (2) ÅCell parameters from 7731 reflections
b = 13.2497 (2) Åθ = 2.5–27.4°
c = 15.6671 (2) ŵ = 0.57 mm−1
α = 69.277 (1)°T = 295 K
β = 77.067 (1)°Plate, yellow
γ = 87.328 (1)°0.39 × 0.31 × 0.09 mm
V = 1700.12 (5) Å3
Data collection top
Bruker APEX II CCD
diffractometer		7692 independent reflections
Radiation source: fine-focus sealed tube6662 reflections with I > 2σ(I)
graphiteRint = 0.022
φ and ω scansθmax = 27.4°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −11→11
Tmin = 0.813, Tmax = 0.951k = −17→17
29003 measured reflectionsl = −20→19
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0966P)2 + 1.4193P]
where P = (Fo2 + 2Fc2)/3
7692 reflections(Δ/σ)max = 0.001
451 parametersΔρmax = 0.70 e Å−3
24 restraintsΔρmin = −0.77 e Å−3
Crystal data top
[Co(C12H14O4)(C12H8N2)2(H2O)]·4H2Oγ = 87.328 (1)°
Mr = 731.65V = 1700.12 (5) Å3
Triclinic, P1Z = 2
a = 8.9902 (2) ÅMo Kα radiation
b = 13.2497 (2) ŵ = 0.57 mm−1
c = 15.6671 (2) ÅT = 295 K
α = 69.277 (1)°0.39 × 0.31 × 0.09 mm
β = 77.067 (1)°
Data collection top
Bruker APEX II CCD
diffractometer		7692 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		6662 reflections with I > 2σ(I)
Tmin = 0.813, Tmax = 0.951Rint = 0.022
29003 measured reflectionsθmax = 27.4°
Refinement top
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.167Δρmax = 0.70 e Å−3
S = 1.06Δρmin = −0.77 e Å−3
7692 reflectionsAbsolute structure: ?
451 parametersFlack parameter: ?
24 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.77668 (4)0.73276 (3)0.75869 (2)0.03448 (13)
O10.6078 (2)0.83204 (14)0.80147 (12)0.0363 (4)
O20.4719 (3)0.8737 (2)0.69354 (19)0.0733 (9)
O30.1345 (3)1.27607 (18)0.67492 (17)0.0592 (6)
O40.3830 (2)1.29932 (16)0.61730 (14)0.0505 (5)
O1w0.6634 (3)0.73629 (19)0.65170 (16)0.0555 (6)
H1w10.58670.77610.65300.083*
H1w20.63350.67250.66090.083*
O2w0.6797 (4)0.6062 (2)0.55445 (16)0.0676 (7)
H2w10.66020.63910.50060.101*
H2w20.77080.58260.54690.101*
O3w0.6600 (3)0.3795 (2)0.6404 (2)0.0763 (8)
H3w10.58980.35200.62530.114*
H3w20.74550.37180.60580.114*
O4w0.9756 (4)0.3754 (3)0.5430 (2)0.1015 (11)
H4w11.02740.34330.58380.152*
H4w20.98180.33940.50570.152*
O5w0.8633 (4)0.3016 (4)0.7950 (3)0.1137 (13)
H5w10.95000.29250.76220.171*
H5w20.80280.32310.75710.171*
N10.9384 (2)0.87944 (17)0.67661 (14)0.0344 (4)
N20.9945 (2)0.67309 (17)0.68646 (14)0.0340 (4)
N30.6912 (2)0.55917 (16)0.84887 (14)0.0309 (4)
N40.8511 (2)0.68960 (15)0.89783 (13)0.0273 (4)
C10.9074 (4)0.9812 (2)0.6682 (2)0.0433 (6)
H10.81630.99480.70360.052*
C21.0050 (4)1.0683 (2)0.6089 (2)0.0517 (7)
H20.97871.13840.60450.062*
C31.1392 (4)1.0497 (3)0.5574 (2)0.0532 (8)
H31.20551.10720.51750.064*
C41.1780 (3)0.9432 (2)0.56434 (18)0.0434 (6)
C51.3174 (3)0.9163 (3)0.5126 (2)0.0559 (9)
H51.38700.97120.47170.067*
C61.3490 (3)0.8135 (3)0.5221 (2)0.0554 (8)
H61.44120.79830.48870.066*
C71.2439 (3)0.7268 (3)0.58235 (18)0.0450 (6)
C81.2697 (4)0.6184 (3)0.5932 (2)0.0544 (8)
H81.36250.59920.56370.065*
C91.1598 (4)0.5413 (3)0.6466 (2)0.0520 (7)
H91.17570.46930.65340.062*
C101.0223 (3)0.5719 (2)0.69122 (19)0.0413 (6)
H100.94630.51890.72610.050*
C111.1034 (3)0.7501 (2)0.63264 (16)0.0341 (5)
C121.0721 (3)0.8606 (2)0.62498 (16)0.0342 (5)
C130.6101 (3)0.4955 (2)0.8254 (2)0.0394 (5)
H130.59200.52000.76540.047*
C140.5510 (3)0.3934 (2)0.8872 (2)0.0452 (6)
H140.49450.35170.86820.054*
C150.5765 (3)0.3556 (2)0.9748 (2)0.0412 (6)
H150.53650.28831.01650.049*
C160.6643 (3)0.41909 (18)1.00232 (18)0.0333 (5)
C170.6976 (3)0.3850 (2)1.09303 (19)0.0409 (6)
H170.66020.31811.13680.049*
C180.7823 (3)0.4483 (2)1.11631 (18)0.0400 (6)
H180.80450.42371.17530.048*
C190.8386 (3)0.55296 (19)1.05137 (16)0.0310 (5)
C200.9240 (3)0.6234 (2)1.07304 (18)0.0371 (5)
H200.94880.60201.13130.045*
C210.9700 (3)0.7228 (2)1.00833 (19)0.0380 (5)
H211.02730.76981.02160.046*
C220.9300 (3)0.75346 (19)0.92164 (18)0.0342 (5)
H220.96040.82210.87850.041*
C230.8062 (2)0.58983 (17)0.96187 (15)0.0260 (4)
C240.7189 (2)0.52079 (17)0.93618 (16)0.0278 (4)
C250.5087 (3)0.88646 (18)0.76021 (16)0.0290 (4)
C260.4244 (2)0.96943 (17)0.79885 (15)0.0249 (4)
C270.2706 (3)0.91488 (18)0.86213 (18)0.0342 (5)
H27A0.21360.89210.82600.041*
H27B0.28950.85130.91270.041*
C280.1772 (3)0.99344 (19)0.90258 (17)0.0347 (5)
H28A0.08020.95780.94260.042*
C290.1454 (3)1.09256 (19)0.82272 (17)0.0321 (5)
H29A0.08541.14230.84820.039*
H29B0.08711.07070.78660.039*
C300.2957 (2)1.14894 (17)0.75907 (15)0.0262 (4)
C310.3852 (3)1.18280 (18)0.81816 (16)0.0303 (5)
H31A0.48091.21900.77890.036*
H31B0.32651.23290.84370.036*
C320.4172 (3)1.0835 (2)0.89789 (16)0.0320 (5)
H32A0.47461.10620.93480.038*
C330.5125 (3)1.00539 (19)0.85689 (16)0.0300 (5)
H33A0.60871.04080.81770.036*
H33B0.53470.94280.90720.036*
C340.2674 (3)1.0273 (2)0.96088 (17)0.0397 (6)
H34A0.20821.07590.98820.048*
H34B0.28800.96421.01130.048*
C350.3915 (2)1.06957 (17)0.71942 (15)0.0259 (4)
H35A0.33681.04770.68170.031*
H35B0.48721.10520.67950.031*
C360.2686 (3)1.24950 (19)0.67744 (17)0.0344 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0349 (2)0.0314 (2)0.0364 (2)0.00510 (14)−0.00779 (14)−0.01162 (14)
O10.0384 (9)0.0373 (9)0.0373 (9)0.0179 (7)−0.0151 (7)−0.0164 (7)
O20.1009 (19)0.0826 (17)0.0847 (17)0.0644 (16)−0.0679 (16)−0.0664 (15)
O30.0485 (12)0.0522 (12)0.0643 (14)0.0218 (10)−0.0229 (11)−0.0017 (10)
O40.0548 (12)0.0409 (10)0.0415 (11)0.0051 (9)−0.0130 (9)0.0037 (8)
O1w0.0627 (13)0.0641 (14)0.0657 (14)0.0315 (11)−0.0372 (11)−0.0439 (12)
O2w0.114 (2)0.0533 (13)0.0486 (12)0.0234 (13)−0.0352 (13)−0.0253 (11)
O3w0.0752 (17)0.0716 (17)0.0724 (17)−0.0151 (14)−0.0187 (14)−0.0103 (13)
O4w0.085 (2)0.138 (3)0.086 (2)0.031 (2)−0.0518 (18)−0.029 (2)
O5w0.092 (2)0.147 (3)0.102 (3)0.049 (2)−0.014 (2)−0.054 (2)
N10.0387 (11)0.0315 (10)0.0309 (10)0.0000 (8)−0.0064 (8)−0.0091 (8)
N20.0368 (10)0.0351 (10)0.0297 (10)0.0074 (8)−0.0076 (8)−0.0117 (8)
N30.0287 (9)0.0299 (9)0.0362 (10)0.0006 (7)−0.0074 (8)−0.0142 (8)
N40.0239 (8)0.0238 (8)0.0323 (9)0.0004 (7)−0.0041 (7)−0.0086 (7)
C10.0518 (15)0.0335 (13)0.0440 (14)0.0004 (11)−0.0118 (12)−0.0122 (11)
C20.072 (2)0.0324 (13)0.0526 (17)−0.0076 (13)−0.0249 (16)−0.0089 (12)
C30.0631 (19)0.0504 (16)0.0394 (15)−0.0260 (14)−0.0178 (14)−0.0004 (12)
C40.0434 (14)0.0561 (16)0.0275 (12)−0.0148 (12)−0.0114 (10)−0.0067 (11)
C50.0390 (14)0.088 (3)0.0316 (13)−0.0221 (15)−0.0024 (11)−0.0101 (14)
C60.0347 (14)0.093 (3)0.0340 (14)−0.0021 (15)−0.0008 (11)−0.0203 (15)
C70.0339 (12)0.0724 (19)0.0304 (12)0.0074 (12)−0.0069 (10)−0.0211 (13)
C80.0452 (15)0.081 (2)0.0447 (16)0.0286 (16)−0.0123 (13)−0.0339 (16)
C90.0604 (18)0.0557 (17)0.0480 (16)0.0275 (15)−0.0182 (14)−0.0277 (14)
C100.0466 (14)0.0398 (13)0.0396 (13)0.0137 (11)−0.0126 (11)−0.0162 (11)
C110.0299 (11)0.0466 (14)0.0252 (11)0.0034 (10)−0.0062 (9)−0.0121 (10)
C120.0351 (12)0.0418 (13)0.0251 (11)−0.0037 (10)−0.0089 (9)−0.0090 (9)
C130.0387 (13)0.0388 (13)0.0463 (14)−0.0006 (10)−0.0115 (11)−0.0205 (11)
C140.0378 (13)0.0367 (13)0.0696 (19)−0.0038 (11)−0.0100 (13)−0.0296 (13)
C150.0349 (12)0.0249 (11)0.0602 (17)−0.0037 (9)−0.0029 (11)−0.0148 (11)
C160.0278 (10)0.0234 (10)0.0452 (13)0.0015 (8)−0.0018 (9)−0.0118 (10)
C170.0442 (14)0.0246 (11)0.0418 (14)0.0008 (10)−0.0031 (11)−0.0010 (10)
C180.0450 (14)0.0337 (12)0.0331 (12)0.0033 (10)−0.0082 (11)−0.0025 (10)
C190.0293 (11)0.0294 (11)0.0311 (11)0.0048 (9)−0.0058 (9)−0.0081 (9)
C200.0374 (12)0.0439 (14)0.0326 (12)0.0049 (10)−0.0112 (10)−0.0149 (10)
C210.0364 (12)0.0386 (13)0.0441 (14)−0.0029 (10)−0.0101 (11)−0.0197 (11)
C220.0331 (11)0.0288 (11)0.0388 (13)−0.0038 (9)−0.0066 (10)−0.0099 (9)
C230.0215 (9)0.0242 (10)0.0309 (11)0.0036 (7)−0.0037 (8)−0.0096 (8)
C240.0233 (9)0.0233 (10)0.0354 (11)0.0039 (8)−0.0038 (8)−0.0108 (9)
C250.0316 (11)0.0251 (10)0.0310 (11)0.0062 (8)−0.0079 (9)−0.0104 (8)
C260.0254 (10)0.0238 (9)0.0257 (10)0.0056 (8)−0.0077 (8)−0.0083 (8)
C270.0320 (11)0.0254 (10)0.0397 (13)0.0017 (9)−0.0029 (10)−0.0079 (9)
C280.0276 (11)0.0313 (11)0.0369 (12)0.0013 (9)0.0025 (9)−0.0079 (10)
C290.0254 (10)0.0322 (11)0.0416 (13)0.0072 (9)−0.0094 (9)−0.0159 (10)
C300.0281 (10)0.0238 (10)0.0286 (10)0.0064 (8)−0.0102 (8)−0.0099 (8)
C310.0341 (11)0.0284 (10)0.0335 (11)0.0026 (9)−0.0101 (9)−0.0158 (9)
C320.0352 (11)0.0392 (12)0.0291 (11)0.0088 (10)−0.0135 (9)−0.0182 (10)
C330.0308 (11)0.0361 (11)0.0270 (10)0.0092 (9)−0.0126 (9)−0.0130 (9)
C340.0444 (14)0.0444 (14)0.0261 (11)0.0128 (11)−0.0031 (10)−0.0116 (10)
C350.0303 (10)0.0249 (10)0.0244 (10)0.0063 (8)−0.0099 (8)−0.0093 (8)
C360.0454 (13)0.0266 (11)0.0344 (12)0.0107 (10)−0.0166 (10)−0.0111 (9)
Geometric parameters (Å, °) top
Co1—O12.114 (2)C13—C141.400 (4)
Co1—O1w2.134 (2)C13—H130.9300
Co1—N12.281 (2)C14—C151.352 (4)
Co1—N22.288 (2)C14—H140.9300
Co1—N32.293 (2)C15—C161.410 (3)
Co1—N42.294 (2)C15—H150.9300
C25—O11.264 (3)C16—C241.406 (3)
C25—O21.231 (3)C16—C171.427 (4)
C36—O31.246 (3)C17—C181.348 (4)
C36—O41.253 (3)C17—H170.9300
O1w—H1w10.85C18—C191.432 (3)
O1w—H1w20.85C18—H180.9300
O2w—H2w10.86C19—C231.405 (3)
O2w—H2w20.86C19—C201.408 (3)
O3w—H3w10.86C20—C211.362 (4)
O3w—H3w20.86C20—H200.9300
O4w—H4w10.85C21—C221.398 (4)
O4w—H4w20.87C21—H210.9300
O5w—H5w10.86C22—H220.9300
O5w—H5w20.86C23—C241.443 (3)
N1—C11.330 (3)C25—C261.529 (3)
N1—C121.357 (3)C26—C331.531 (3)
N2—C101.331 (3)C26—C351.535 (3)
N2—C111.352 (3)C26—C271.546 (3)
N3—C131.331 (3)C27—C281.529 (3)
N3—C241.357 (3)C27—H27A0.9700
N4—C221.325 (3)C27—H27B0.9700
N4—C231.359 (3)C28—C291.528 (3)
C1—C21.392 (4)C28—C341.533 (4)
C1—H10.9300C28—H28A0.9800
C2—C31.358 (5)C29—C301.530 (3)
C2—H20.9300C29—H29A0.9700
C3—C41.409 (5)C29—H29B0.9700
C3—H30.9300C30—C311.538 (3)
C4—C121.401 (4)C30—C351.540 (3)
C4—C51.436 (5)C30—C361.540 (3)
C5—C61.341 (5)C31—C321.528 (3)
C5—H50.9300C31—H31A0.9700
C6—C71.427 (5)C31—H31B0.9700
C6—H60.9300C32—C341.524 (4)
C7—C81.401 (5)C32—C331.536 (3)
C7—C111.414 (3)C32—H32A0.9800
C8—C91.356 (5)C33—H33A0.9700
C8—H80.9300C33—H33B0.9700
C9—C101.395 (4)C34—H34A0.9700
C9—H90.9300C34—H34B0.9700
C10—H100.9300C35—H35A0.9700
C11—C121.445 (4)C35—H35B0.9700
O1—Co1—O1w89.16 (7)C17—C18—H18119.6
O1—Co1—N190.53 (8)C19—C18—H18119.6
O1w—Co1—N198.86 (9)C23—C19—C20117.3 (2)
O1—Co1—N2163.25 (8)C23—C19—C18119.6 (2)
O1w—Co1—N291.39 (8)C20—C19—C18123.1 (2)
N1—Co1—N272.85 (8)C21—C20—C19119.7 (2)
O1—Co1—N3105.30 (7)C21—C20—H20120.2
O1w—Co1—N392.71 (9)C19—C20—H20120.2
N1—Co1—N3160.55 (8)C20—C21—C22119.1 (2)
N2—Co1—N391.39 (7)C20—C21—H21120.5
O1—Co1—N489.86 (7)C22—C21—H21120.5
O1w—Co1—N4164.05 (9)N4—C22—C21123.3 (2)
N1—Co1—N497.07 (7)N4—C22—H22118.3
N2—Co1—N494.11 (7)C21—C22—H22118.3
N3—Co1—N472.22 (7)N4—C23—C19122.8 (2)
C25—O1—Co1130.01 (15)N4—C23—C24117.70 (19)
Co1—O1w—H1w1109.6C19—C23—C24119.5 (2)
Co1—O1w—H1w2109.5N3—C24—C16123.2 (2)
H1w1—O1w—H1w2109.4N3—C24—C23117.56 (19)
H2w1—O2w—H2w2108.6C16—C24—C23119.2 (2)
H3w1—O3w—H3w2107.0O2—C25—O1124.1 (2)
H4w1—O4w—H4w2108.0O2—C25—C26118.2 (2)
H5w1—O5w—H5w2106.2O1—C25—C26117.65 (19)
C1—N1—C12118.0 (2)C25—C26—C33112.78 (17)
C1—N1—Co1126.02 (19)C25—C26—C35110.93 (17)
C12—N1—Co1115.71 (16)C33—C26—C35108.73 (17)
C10—N2—C11117.8 (2)C25—C26—C27106.81 (18)
C10—N2—Co1126.68 (18)C33—C26—C27108.89 (19)
C11—N2—Co1115.51 (16)C35—C26—C27108.59 (18)
C13—N3—C24117.5 (2)C28—C27—C26110.27 (19)
C13—N3—Co1126.11 (17)C28—C27—H27A109.6
C24—N3—Co1116.30 (14)C26—C27—H27A109.6
C22—N4—C23117.8 (2)C28—C27—H27B109.6
C22—N4—Co1126.09 (16)C26—C27—H27B109.6
C23—N4—Co1116.12 (14)H27A—C27—H27B108.1
N1—C1—C2123.0 (3)C29—C28—C27109.4 (2)
N1—C1—H1118.5C29—C28—C34110.0 (2)
C2—C1—H1118.5C27—C28—C34109.1 (2)
C3—C2—C1119.2 (3)C29—C28—H28A109.4
C3—C2—H2120.4C27—C28—H28A109.4
C1—C2—H2120.4C34—C28—H28A109.4
C2—C3—C4120.0 (3)C28—C29—C30110.18 (18)
C2—C3—H3120.0C28—C29—H29A109.6
C4—C3—H3120.0C30—C29—H29A109.6
C12—C4—C3117.0 (3)C28—C29—H29B109.6
C12—C4—C5119.4 (3)C30—C29—H29B109.6
C3—C4—C5123.7 (3)H29A—C29—H29B108.1
C6—C5—C4121.3 (3)C29—C30—C31108.37 (19)
C6—C5—H5119.4C29—C30—C35109.55 (18)
C4—C5—H5119.4C31—C30—C35108.49 (17)
C5—C6—C7121.3 (3)C29—C30—C36111.84 (19)
C5—C6—H6119.4C31—C30—C36109.32 (18)
C7—C6—H6119.4C35—C30—C36109.21 (18)
C8—C7—C11117.1 (3)C32—C31—C30110.08 (18)
C8—C7—C6123.6 (3)C32—C31—H31A109.6
C11—C7—C6119.3 (3)C30—C31—H31A109.6
C9—C8—C7120.2 (3)C32—C31—H31B109.6
C9—C8—H8119.9C30—C31—H31B109.6
C7—C8—H8119.9H31A—C31—H31B108.2
C8—C9—C10118.9 (3)C34—C32—C31110.0 (2)
C8—C9—H9120.6C34—C32—C33109.7 (2)
C10—C9—H9120.6C31—C32—C33109.38 (18)
N2—C10—C9123.3 (3)C34—C32—H32A109.2
N2—C10—H10118.3C31—C32—H32A109.2
C9—C10—H10118.3C33—C32—H32A109.2
N2—C11—C7122.6 (3)C26—C33—C32109.86 (17)
N2—C11—C12118.1 (2)C26—C33—H33A109.7
C7—C11—C12119.3 (2)C32—C33—H33A109.7
N1—C12—C4122.9 (3)C26—C33—H33B109.7
N1—C12—C11117.7 (2)C32—C33—H33B109.7
C4—C12—C11119.4 (2)H33A—C33—H33B108.2
N3—C13—C14122.9 (3)C32—C34—C28109.04 (19)
N3—C13—H13118.6C32—C34—H34A109.9
C14—C13—H13118.6C28—C34—H34A109.9
C15—C14—C13119.8 (2)C32—C34—H34B109.9
C15—C14—H14120.1C28—C34—H34B109.9
C13—C14—H14120.1H34A—C34—H34B108.3
C14—C15—C16119.5 (2)C26—C35—C30110.72 (17)
C14—C15—H15120.2C26—C35—H35A109.5
C16—C15—H15120.2C30—C35—H35A109.5
C24—C16—C15117.1 (2)C26—C35—H35B109.5
C24—C16—C17119.7 (2)C30—C35—H35B109.5
C15—C16—C17123.1 (2)H35A—C35—H35B108.1
C18—C17—C16121.1 (2)O3—C36—O4124.0 (2)
C18—C17—H17119.4O3—C36—C30118.1 (2)
C16—C17—H17119.4O4—C36—C30118.0 (2)
C17—C18—C19120.9 (2)
O1w—Co1—O1—C25−14.0 (2)C24—N3—C13—C141.4 (4)
N1—Co1—O1—C2584.9 (2)Co1—N3—C13—C14−174.56 (19)
N2—Co1—O1—C2578.1 (3)N3—C13—C14—C15−0.4 (4)
N3—Co1—O1—C25−106.5 (2)C13—C14—C15—C16−0.9 (4)
N4—Co1—O1—C25−178.0 (2)C14—C15—C16—C241.1 (4)
O1—Co1—N1—C1−1.6 (2)C14—C15—C16—C17−179.5 (2)
O1w—Co1—N1—C187.7 (2)C24—C16—C17—C18−0.8 (4)
N2—Co1—N1—C1176.4 (2)C15—C16—C17—C18179.9 (3)
N3—Co1—N1—C1−146.5 (2)C16—C17—C18—C191.5 (4)
N4—Co1—N1—C1−91.5 (2)C17—C18—C19—C23−0.6 (4)
O1—Co1—N1—C12−174.87 (16)C17—C18—C19—C20178.2 (3)
O1w—Co1—N1—C12−85.65 (17)C23—C19—C20—C210.6 (4)
N2—Co1—N1—C123.07 (16)C18—C19—C20—C21−178.2 (2)
N3—Co1—N1—C1240.2 (3)C19—C20—C21—C220.6 (4)
N4—Co1—N1—C1295.21 (16)C23—N4—C22—C210.7 (3)
O1—Co1—N2—C10−172.9 (2)Co1—N4—C22—C21179.00 (18)
O1w—Co1—N2—C10−81.2 (2)C20—C21—C22—N4−1.3 (4)
N1—Co1—N2—C10179.9 (2)C22—N4—C23—C190.6 (3)
N3—Co1—N2—C1011.5 (2)Co1—N4—C23—C19−177.88 (16)
N4—Co1—N2—C1083.8 (2)C22—N4—C23—C24179.4 (2)
O1—Co1—N2—C116.0 (3)Co1—N4—C23—C240.9 (2)
O1w—Co1—N2—C1197.68 (17)C20—C19—C23—N4−1.2 (3)
N1—Co1—N2—C11−1.17 (16)C18—C19—C23—N4177.6 (2)
N3—Co1—N2—C11−169.58 (17)C20—C19—C23—C24−180.0 (2)
N4—Co1—N2—C11−97.31 (16)C18—C19—C23—C24−1.1 (3)
O1—Co1—N3—C1394.0 (2)C13—N3—C24—C16−1.1 (3)
O1w—Co1—N3—C134.1 (2)Co1—N3—C24—C16175.24 (17)
N1—Co1—N3—C13−122.6 (3)C13—N3—C24—C23−179.7 (2)
N2—Co1—N3—C13−87.4 (2)Co1—N3—C24—C23−3.4 (2)
N4—Co1—N3—C13178.8 (2)C15—C16—C24—N3−0.1 (3)
O1—Co1—N3—C24−82.01 (16)C17—C16—C24—N3−179.5 (2)
O1w—Co1—N3—C24−171.88 (16)C15—C16—C24—C23178.5 (2)
N1—Co1—N3—C2461.5 (3)C17—C16—C24—C23−0.9 (3)
N2—Co1—N3—C2496.67 (16)N4—C23—C24—N31.7 (3)
N4—Co1—N3—C242.80 (15)C19—C23—C24—N3−179.50 (19)
O1—Co1—N4—C22−74.12 (19)N4—C23—C24—C16−176.99 (19)
O1w—Co1—N4—C22−160.5 (2)C19—C23—C24—C161.8 (3)
N1—Co1—N4—C2216.4 (2)Co1—O1—C25—O215.9 (4)
N2—Co1—N4—C2289.59 (19)Co1—O1—C25—C26−167.12 (15)
N3—Co1—N4—C22179.7 (2)O2—C25—C26—C33−160.6 (3)
O1—Co1—N4—C23104.25 (15)O1—C25—C26—C3322.3 (3)
O1w—Co1—N4—C2317.8 (3)O2—C25—C26—C35−38.4 (3)
N1—Co1—N4—C23−165.24 (15)O1—C25—C26—C35144.5 (2)
N2—Co1—N4—C23−92.03 (15)O2—C25—C26—C2779.8 (3)
N3—Co1—N4—C23−1.89 (14)O1—C25—C26—C27−97.3 (2)
C12—N1—C1—C20.4 (4)C25—C26—C27—C28−179.01 (19)
Co1—N1—C1—C2−172.8 (2)C33—C26—C27—C2858.9 (2)
N1—C1—C2—C3−0.6 (4)C35—C26—C27—C28−59.3 (2)
C1—C2—C3—C40.0 (4)C26—C27—C28—C2960.2 (3)
C2—C3—C4—C120.7 (4)C26—C27—C28—C34−60.2 (3)
C2—C3—C4—C5−179.9 (3)C27—C28—C29—C30−59.8 (3)
C12—C4—C5—C6−0.9 (4)C34—C28—C29—C3060.1 (2)
C3—C4—C5—C6179.8 (3)C28—C29—C30—C31−59.4 (2)
C4—C5—C6—C71.5 (4)C28—C29—C30—C3558.7 (2)
C5—C6—C7—C8178.5 (3)C28—C29—C30—C36179.98 (19)
C5—C6—C7—C110.3 (4)C29—C30—C31—C3259.5 (2)
C11—C7—C8—C93.0 (4)C35—C30—C31—C32−59.3 (2)
C6—C7—C8—C9−175.3 (3)C36—C30—C31—C32−178.34 (19)
C7—C8—C9—C10−0.9 (4)C30—C31—C32—C34−60.3 (2)
C11—N2—C10—C92.6 (4)C30—C31—C32—C3360.2 (2)
Co1—N2—C10—C9−178.6 (2)C25—C26—C33—C32−176.82 (19)
C8—C9—C10—N2−2.1 (4)C35—C26—C33—C3259.7 (2)
C10—N2—C11—C7−0.2 (3)C27—C26—C33—C32−58.4 (2)
Co1—N2—C11—C7−179.19 (18)C34—C32—C33—C2660.4 (2)
C10—N2—C11—C12178.2 (2)C31—C32—C33—C26−60.4 (2)
Co1—N2—C11—C12−0.8 (3)C31—C32—C34—C2859.3 (2)
C8—C7—C11—N2−2.5 (4)C33—C32—C34—C28−61.0 (2)
C6—C7—C11—N2175.8 (2)C29—C28—C34—C32−59.2 (2)
C8—C7—C11—C12179.1 (2)C27—C28—C34—C3260.9 (3)
C6—C7—C11—C12−2.6 (4)C25—C26—C35—C30175.56 (18)
C1—N1—C12—C40.4 (3)C33—C26—C35—C30−59.9 (2)
Co1—N1—C12—C4174.31 (18)C27—C26—C35—C3058.5 (2)
C1—N1—C12—C11−178.5 (2)C29—C30—C35—C26−58.7 (2)
Co1—N1—C12—C11−4.6 (3)C31—C30—C35—C2659.5 (2)
C3—C4—C12—N1−1.0 (4)C36—C30—C35—C26178.53 (18)
C5—C4—C12—N1179.6 (2)C29—C30—C36—O33.6 (3)
C3—C4—C12—C11177.9 (2)C31—C30—C36—O3−116.4 (3)
C5—C4—C12—C11−1.5 (3)C35—C30—C36—O3125.0 (2)
N2—C11—C12—N13.6 (3)C29—C30—C36—O4−176.1 (2)
C7—C11—C12—N1−177.9 (2)C31—C30—C36—O463.9 (3)
N2—C11—C12—C4−175.3 (2)C35—C30—C36—O4−54.6 (3)
C7—C11—C12—C43.2 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O20.851.822.599 (3)152
O1w—H1w2···O2w0.852.102.656 (3)122
O2w—H2w1···O4i0.861.862.712 (3)176
O2w—H2w2···O4wii0.862.373.113 (5)145
O3w—H3w1···O4iii0.862.062.895 (4)164
O3w—H3w2···O4w0.862.082.913 (5)164
O4w—H4w1···O3iv0.851.842.695 (3)178
O5w—H5w1···O3iv0.861.962.814 (4)173
O5w—H5w2···O3w0.862.363.211 (5)174
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y−1, z.
Table 1
Selected geometric parameters (Å) top
Co1—O12.114 (2)Co1—N22.288 (2)
Co1—O1w2.134 (2)Co1—N32.293 (2)
Co1—N12.281 (2)Co1—N42.294 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O20.851.822.599 (3)152
O1w—H1w2···O2w0.852.102.656 (3)122
O2w—H2w1···O4i0.861.862.712 (3)176
O2w—H2w2···O4wii0.862.373.113 (5)145
O3w—H3w1···O4iii0.862.062.895 (4)164
O3w—H3w2···O4w0.862.082.913 (5)164
O4w—H4w1···O3iv0.851.842.695 (3)178
O5w—H5w1···O3iv0.861.962.814 (4)173
O5w—H5w2···O3w0.862.363.211 (5)174
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y−1, z; (iv) x+1, y−1, z.
Acknowledgements top

We thank Zhejiang Normal University and the University of Malaya for supporting this work.

references
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