catena-Poly[[[aqua­(2,2′-bipyridine)cobalt(II)]-μ-5-nitro­benzene-1,3-dicarboxyl­ato-κ3O:O′,O′′] 0.25-hydrate]

Xie, G.; Zeng, M.-H.; Chen, S.-P.; Gao, S.-L.

doi:10.1107/S1600536806002704

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catena-Poly[[[aqua(2,2′-bipyridine)cobalt(II)]-μ-5-nitrobenzene-1,3-dicarboxylato-κ³O:O′,O′′] 0.25-hydrate]

G. Xie, M.-H. Zeng, S.-P. Chen and S.-L. Gao

In the title compound, {[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·0.25H₂O}_n, the coordination polyhedron of the Co^II ion is an octahedron. Each pair of adjacent Co^II ions is bridged by a dianion of 5-nitro-1,3-benzenedicarboxylic acid (H₂nmbdc) to form a chain running along the a axis. These chains are linked by π–π stacking interactions and O(water)—H

O hydrogen bonds into a supramolecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002704/bv6044sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002704/bv6044Isup2.hkl Contains datablock I

CCDC reference: 298380

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
Disorder in solvent or counterion
R factor = 0.038
wR factor = 0.112
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.12 Ratio
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT213_ALERT_2_C Atom O6      has ADP max/min Ratio .............       3.60 prolat
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.43 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT731_ALERT_1_C Bond    Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O13W -H13B    1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.85(3), Rep   0.850(10) ......       3.00 su-Rat
              O13W -H13B    1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  14 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

catena-Poly[[aqua(2,2'-bipyridine)cobalt(II)]-µ-5-nitrobenzene-1,3- dicarboxylato-κ³O:O',O''] 0.25-hydrate] top

Crystal data top

[Co(C₈H₃NO₆)(C₁₀H₈N₂)(H₂O)]·0.25H₂O	F(000) = 1820
M_r = 446.75	D_x = 1.650 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3310 reflections
a = 10.0561 (2) Å	θ = 2.5–23.3°
b = 23.3986 (5) Å	µ = 1.01 mm⁻¹
c = 15.3811 (3) Å	T = 293 K
β = 96.317 (1)°	Block, red
V = 3597.18 (13) Å³	0.26 × 0.14 × 0.12 mm
Z = 8

Data collection top

Bruker APEX area-detector diffractometer	7054 independent reflections
Radiation source: fine-focus sealed tube	4747 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
φ and ω scans	θ_max = 26.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −12→12
T_min = 0.780, T_max = 0.889	k = −25→28
28059 measured reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H-atom parameters constrained
S = 0.95	w = 1/[σ²(F_o²) + (0.0675P)²] where P = (F_o² + 2F_c²)/3
7054 reflections	(Δ/σ)_max = 0.001
548 parameters	Δρ_max = 0.66 e Å⁻³
6 restraints	Δρ_min = −0.61 e Å⁻³

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Co1	0.65887 (4)	0.153602 (15)	0.35708 (2)	0.02924 (12)
Co2	0.62890 (4)	0.354806 (15)	0.43390 (3)	0.03239 (12)
C1	0.7020 (4)	0.06948 (14)	0.5082 (2)	0.0527 (9)
H1	0.7224	0.1018	0.5423	0.063*
C2	0.7087 (4)	0.01718 (16)	0.5480 (2)	0.0678 (11)
H2	0.7335	0.0141	0.6079	0.081*
C3	0.6786 (4)	−0.03087 (16)	0.4984 (3)	0.0700 (12)
H3	0.6802	−0.0668	0.5242	0.084*
C4	0.6459 (4)	−0.02471 (14)	0.4099 (2)	0.0538 (9)
H4	0.6275	−0.0567	0.3748	0.065*
C5	0.6405 (3)	0.02927 (12)	0.37304 (19)	0.0343 (7)
C6	0.6087 (3)	0.03962 (11)	0.27789 (18)	0.0316 (6)
C7	0.5816 (3)	−0.00290 (13)	0.2168 (2)	0.0422 (7)
H7	0.5813	−0.0409	0.2343	0.051*
C8	0.5548 (3)	0.01093 (14)	0.1299 (2)	0.0470 (8)
H8	0.5365	−0.0176	0.0882	0.056*
C9	0.5554 (3)	0.06725 (14)	0.1055 (2)	0.0453 (8)
H9	0.5369	0.0777	0.0471	0.054*
C10	0.5840 (3)	0.10791 (13)	0.16926 (19)	0.0390 (7)
H10	0.5846	0.1461	0.1526	0.047*
C11	1.0118 (3)	0.21754 (12)	0.29309 (18)	0.0319 (6)
C12	1.1301 (3)	0.18902 (12)	0.32003 (18)	0.0318 (6)
H12	1.1264	0.1539	0.3480	0.038*
C13	1.2541 (3)	0.21149 (11)	0.30630 (17)	0.0285 (6)
C14	1.2594 (3)	0.26387 (12)	0.26557 (18)	0.0330 (6)
H14	1.3410	0.2797	0.2552	0.040*
C15	1.1410 (3)	0.29225 (12)	0.24055 (18)	0.0358 (7)
C16	1.0170 (3)	0.27030 (12)	0.25225 (19)	0.0371 (7)
H16	0.9391	0.2902	0.2334	0.044*
C17	0.8789 (3)	0.19303 (14)	0.3113 (2)	0.0395 (7)
C18	1.3804 (3)	0.17889 (12)	0.33731 (18)	0.0352 (7)
C19	0.5849 (3)	0.44158 (14)	0.2858 (2)	0.0445 (8)
H19	0.5721	0.4097	0.2498	0.053*
C20	0.5692 (3)	0.49524 (15)	0.2487 (2)	0.0533 (9)
H20	0.5460	0.4996	0.1889	0.064*
C21	0.5887 (3)	0.54226 (15)	0.3028 (3)	0.0550 (9)
H21	0.5801	0.5789	0.2794	0.066*
C22	0.6208 (3)	0.53500 (13)	0.3910 (3)	0.0470 (8)
H22	0.6320	0.5665	0.4279	0.056*
C23	0.6366 (3)	0.47997 (12)	0.4248 (2)	0.0364 (7)
C24	0.6727 (3)	0.46774 (12)	0.5185 (2)	0.0359 (7)
C25	0.7013 (3)	0.50932 (13)	0.5822 (2)	0.0474 (8)
H25	0.6980	0.5478	0.5671	0.057*
C26	0.7347 (3)	0.49318 (15)	0.6676 (2)	0.0531 (9)
H26	0.7532	0.5207	0.7109	0.064*
C27	0.7403 (3)	0.43628 (16)	0.6886 (2)	0.0531 (9)
H27	0.7649	0.4245	0.7459	0.064*
C28	0.7088 (3)	0.39677 (14)	0.6229 (2)	0.0461 (8)
H28	0.7106	0.3581	0.6373	0.055*
C29	0.2774 (3)	0.29044 (11)	0.49980 (18)	0.0310 (6)
C30	0.2705 (3)	0.24022 (12)	0.54744 (18)	0.0346 (7)
H30	0.3476	0.2210	0.5698	0.042*
C31	0.1459 (3)	0.22001 (12)	0.56031 (18)	0.0347 (7)
C32	0.0282 (3)	0.24754 (12)	0.53001 (17)	0.0331 (6)
H32	−0.0541	0.2327	0.5410	0.040*
C33	0.0354 (3)	0.29757 (12)	0.48308 (17)	0.0300 (6)
C34	0.1606 (3)	0.31852 (11)	0.46793 (17)	0.0302 (6)
H34	0.1659	0.3520	0.4358	0.036*
C35	0.4107 (3)	0.31407 (13)	0.4814 (2)	0.0362 (7)
C36	−0.0897 (3)	0.32995 (13)	0.44861 (19)	0.0353 (7)
N1	0.6671 (2)	0.07613 (9)	0.42224 (15)	0.0337 (5)
N2	0.6111 (2)	0.09513 (9)	0.25411 (15)	0.0316 (5)
N3	1.1478 (3)	0.34977 (13)	0.2030 (2)	0.0618 (9)
N4	0.6181 (2)	0.43378 (10)	0.37187 (16)	0.0369 (6)
N5	0.6757 (2)	0.41175 (10)	0.53952 (16)	0.0361 (6)
N6	0.1367 (3)	0.16614 (12)	0.60850 (18)	0.0498 (7)
O1	0.7737 (2)	0.21915 (10)	0.28538 (16)	0.0541 (6)
O2	0.8765 (2)	0.14792 (10)	0.35358 (17)	0.0561 (6)
O3	1.3720 (2)	0.13325 (11)	0.37447 (18)	0.0707 (8)
O4	1.49045 (19)	0.20084 (8)	0.32076 (14)	0.0401 (5)
O5	1.2547 (3)	0.37396 (11)	0.2080 (2)	0.0796 (9)
O6	1.0470 (3)	0.37006 (15)	0.1666 (3)	0.1368 (18)
O7	0.5160 (2)	0.28810 (10)	0.50841 (15)	0.0488 (6)
O8	0.4136 (2)	0.35911 (9)	0.43859 (16)	0.0533 (6)
O9	−0.0802 (2)	0.37362 (10)	0.40642 (16)	0.0586 (7)
O10	−0.20023 (19)	0.30934 (8)	0.46820 (14)	0.0431 (5)
O11	0.0280 (3)	0.14338 (12)	0.6070 (2)	0.0878 (10)
O12	0.2385 (3)	0.14727 (10)	0.64922 (17)	0.0654 (7)
O13W	0.6886 (2)	0.20216 (8)	0.47511 (14)	0.0398 (5)
H13A	0.621 (2)	0.2172 (12)	0.495 (2)	0.063 (12)*
H13B	0.747 (3)	0.2280 (11)	0.471 (3)	0.093 (16)*
O14W	0.6001 (2)	0.30670 (9)	0.31691 (14)	0.0391 (5)
H14B	0.6720 (18)	0.2941 (12)	0.301 (2)	0.062 (12)*
H14C	0.544 (2)	0.2797 (10)	0.319 (3)	0.085 (15)*
O15W	0.4785 (15)	0.5576 (5)	0.0575 (8)	0.258 (7)	0.50
H15A	0.5065	0.5908	0.0453	0.309*	0.50
H15B	0.4874	0.5277	0.0274	0.309*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0255 (2)	0.0231 (2)	0.0390 (2)	0.00154 (15)	0.00267 (15)	0.00216 (15)
Co2	0.0244 (2)	0.0243 (2)	0.0490 (3)	0.00098 (15)	0.00640 (17)	0.00129 (16)
C1	0.072 (3)	0.047 (2)	0.0386 (19)	0.0042 (17)	0.0033 (16)	0.0036 (15)
C2	0.102 (3)	0.057 (2)	0.044 (2)	0.012 (2)	0.005 (2)	0.0197 (18)
C3	0.101 (4)	0.043 (2)	0.065 (3)	−0.001 (2)	0.009 (2)	0.0256 (19)
C4	0.069 (3)	0.0292 (17)	0.064 (2)	−0.0015 (16)	0.0075 (18)	0.0094 (15)
C5	0.0307 (17)	0.0273 (15)	0.0455 (18)	−0.0017 (12)	0.0066 (13)	0.0054 (13)
C6	0.0215 (15)	0.0295 (15)	0.0439 (17)	−0.0003 (11)	0.0039 (12)	0.0003 (12)
C7	0.0375 (19)	0.0285 (16)	0.060 (2)	−0.0027 (13)	0.0045 (15)	−0.0038 (14)
C8	0.038 (2)	0.049 (2)	0.053 (2)	−0.0032 (15)	−0.0014 (15)	−0.0153 (16)
C9	0.045 (2)	0.052 (2)	0.0385 (18)	0.0043 (15)	−0.0003 (14)	−0.0033 (15)
C10	0.0414 (19)	0.0370 (17)	0.0384 (17)	0.0046 (14)	0.0028 (13)	0.0024 (13)
C11	0.0213 (15)	0.0366 (16)	0.0380 (16)	−0.0003 (12)	0.0042 (12)	−0.0087 (12)
C12	0.0282 (17)	0.0279 (15)	0.0401 (15)	−0.0012 (12)	0.0068 (12)	−0.0017 (12)
C13	0.0231 (16)	0.0290 (15)	0.0332 (15)	0.0027 (11)	0.0023 (11)	0.0001 (11)
C14	0.0218 (15)	0.0384 (16)	0.0391 (16)	−0.0016 (12)	0.0047 (12)	0.0044 (12)
C15	0.0345 (18)	0.0354 (16)	0.0385 (16)	0.0062 (13)	0.0081 (13)	0.0120 (12)
C16	0.0247 (17)	0.0455 (18)	0.0409 (17)	0.0082 (13)	0.0032 (12)	0.0021 (13)
C17	0.0259 (18)	0.0458 (19)	0.0480 (18)	−0.0021 (14)	0.0089 (14)	−0.0177 (15)
C18	0.0272 (18)	0.0370 (17)	0.0414 (17)	0.0057 (13)	0.0035 (12)	0.0009 (13)
C19	0.040 (2)	0.0445 (19)	0.050 (2)	0.0031 (14)	0.0095 (15)	0.0041 (15)
C20	0.045 (2)	0.058 (2)	0.059 (2)	0.0100 (17)	0.0131 (17)	0.0207 (18)
C21	0.042 (2)	0.041 (2)	0.084 (3)	0.0058 (15)	0.0181 (18)	0.0218 (19)
C22	0.0356 (19)	0.0294 (17)	0.077 (2)	0.0001 (13)	0.0130 (16)	0.0071 (16)
C23	0.0207 (16)	0.0279 (15)	0.063 (2)	−0.0015 (12)	0.0135 (14)	0.0023 (14)
C24	0.0247 (16)	0.0302 (16)	0.0541 (19)	0.0013 (12)	0.0106 (13)	−0.0038 (13)
C25	0.0341 (19)	0.0344 (18)	0.075 (2)	−0.0023 (14)	0.0119 (16)	−0.0063 (16)
C26	0.040 (2)	0.057 (2)	0.062 (2)	−0.0048 (16)	0.0044 (17)	−0.0186 (18)
C27	0.045 (2)	0.064 (2)	0.050 (2)	0.0031 (17)	0.0039 (16)	−0.0061 (17)
C28	0.041 (2)	0.0436 (19)	0.054 (2)	0.0060 (15)	0.0073 (15)	0.0027 (16)
C29	0.0277 (17)	0.0297 (15)	0.0362 (15)	−0.0018 (12)	0.0060 (12)	−0.0059 (12)
C30	0.0271 (16)	0.0406 (17)	0.0350 (16)	0.0028 (13)	−0.0010 (12)	−0.0006 (13)
C31	0.0316 (18)	0.0352 (16)	0.0369 (16)	−0.0020 (13)	0.0017 (12)	0.0055 (12)
C32	0.0238 (16)	0.0398 (17)	0.0359 (16)	−0.0050 (12)	0.0044 (12)	−0.0007 (13)
C33	0.0237 (16)	0.0336 (16)	0.0326 (15)	0.0015 (11)	0.0021 (11)	−0.0058 (12)
C34	0.0257 (16)	0.0284 (15)	0.0370 (15)	−0.0020 (12)	0.0056 (12)	0.0007 (12)
C35	0.0264 (18)	0.0354 (17)	0.0484 (18)	−0.0014 (13)	0.0115 (13)	−0.0134 (14)
C36	0.0272 (17)	0.0340 (16)	0.0439 (17)	0.0016 (13)	0.0001 (13)	−0.0073 (13)
N1	0.0353 (14)	0.0289 (13)	0.0369 (14)	0.0002 (10)	0.0031 (11)	0.0054 (10)
N2	0.0286 (13)	0.0273 (12)	0.0392 (14)	0.0005 (10)	0.0046 (10)	0.0011 (10)
N3	0.052 (2)	0.056 (2)	0.080 (2)	0.0173 (16)	0.0184 (17)	0.0356 (16)
N4	0.0276 (14)	0.0301 (13)	0.0543 (17)	0.0010 (10)	0.0110 (12)	0.0026 (11)
N5	0.0278 (14)	0.0320 (13)	0.0495 (15)	0.0038 (10)	0.0083 (11)	0.0004 (11)
N6	0.0467 (19)	0.0463 (16)	0.0558 (18)	−0.0004 (14)	0.0033 (14)	0.0151 (13)
O1	0.0247 (13)	0.0592 (15)	0.0793 (17)	0.0027 (11)	0.0097 (11)	−0.0089 (12)
O2	0.0376 (14)	0.0508 (15)	0.0813 (17)	−0.0096 (11)	0.0134 (12)	0.0055 (13)
O3	0.0441 (15)	0.0650 (17)	0.105 (2)	0.0145 (12)	0.0169 (14)	0.0536 (16)
O4	0.0211 (11)	0.0313 (11)	0.0671 (14)	0.0009 (8)	0.0015 (9)	−0.0015 (10)
O5	0.074 (2)	0.0534 (16)	0.109 (2)	−0.0129 (15)	0.0007 (17)	0.0357 (16)
O6	0.055 (2)	0.127 (3)	0.233 (4)	0.043 (2)	0.039 (2)	0.133 (3)
O7	0.0225 (12)	0.0525 (13)	0.0724 (15)	0.0025 (10)	0.0094 (10)	−0.0057 (11)
O8	0.0369 (14)	0.0385 (13)	0.0870 (17)	−0.0075 (10)	0.0183 (12)	0.0072 (12)
O9	0.0416 (15)	0.0537 (15)	0.0801 (17)	0.0100 (11)	0.0048 (12)	0.0261 (13)
O10	0.0200 (11)	0.0351 (11)	0.0736 (15)	0.0007 (9)	0.0026 (10)	−0.0045 (10)
O11	0.0584 (19)	0.086 (2)	0.113 (2)	−0.0310 (16)	−0.0175 (16)	0.0569 (18)
O12	0.0494 (16)	0.0577 (16)	0.0891 (19)	0.0149 (12)	0.0072 (14)	0.0323 (14)
O13W	0.0369 (14)	0.0308 (11)	0.0510 (13)	0.0044 (10)	0.0015 (10)	−0.0042 (9)
O14W	0.0332 (13)	0.0316 (12)	0.0524 (13)	0.0035 (10)	0.0041 (10)	0.0002 (10)
O15W	0.33 (2)	0.200 (12)	0.232 (14)	−0.085 (12)	−0.008 (12)	−0.008 (10)

Geometric parameters (Å, º) top

Co1—N1	2.069 (2)	C19—N4	1.341 (4)
Co1—N2	2.108 (2)	C19—C20	1.381 (4)
Co1—O1	2.276 (2)	C19—H19	0.9300
Co1—O2	2.199 (2)	C20—C21	1.380 (5)
Co1—O4ⁱ	2.048 (2)	C20—H20	0.9300
Co1—O13W	2.135 (2)	C21—C22	1.370 (5)
Co2—N4	2.077 (2)	C21—H21	0.9300
Co2—N5	2.114 (2)	C22—C23	1.391 (4)
Co2—O7	2.307 (2)	C22—H22	0.9300
Co2—O8	2.176 (2)	C23—N4	1.354 (4)
Co2—O10ⁱⁱ	2.040 (2)	C23—C24	1.476 (4)
Co2—O14W	2.115 (2)	C24—N5	1.349 (3)
C1—N1	1.340 (4)	C24—C25	1.388 (4)
C1—C2	1.366 (5)	C25—C26	1.372 (5)
C1—H1	0.9300	C25—H25	0.9300
C2—C3	1.374 (5)	C26—C27	1.370 (5)
C2—H2	0.9300	C26—H26	0.9300
C3—C4	1.371 (5)	C27—C28	1.381 (4)
C3—H3	0.9300	C27—H27	0.9300
C4—C5	1.383 (4)	C28—N5	1.336 (4)
C4—H4	0.9300	C28—H28	0.9300
C5—N1	1.342 (3)	C29—C34	1.387 (4)
C5—C6	1.483 (4)	C29—C30	1.391 (4)
C6—N2	1.350 (3)	C29—C35	1.506 (4)
C6—C7	1.375 (4)	C30—C31	1.373 (4)
C7—C8	1.372 (4)	C30—H30	0.9300
C7—H7	0.9300	C31—C32	1.383 (4)
C8—C9	1.371 (4)	C31—N6	1.470 (4)
C8—H8	0.9300	C32—C33	1.382 (4)
C9—C10	1.373 (4)	C32—H32	0.9300
C9—H9	0.9300	C33—C34	1.394 (4)
C10—N2	1.337 (3)	C33—C36	1.514 (4)
C10—H10	0.9300	C34—H34	0.9300
C11—C12	1.387 (4)	C35—O8	1.245 (4)
C11—C16	1.389 (4)	C35—O7	1.251 (4)
C11—C17	1.509 (4)	C36—O9	1.220 (4)
C12—C13	1.390 (4)	C36—O10	1.278 (3)
C12—H12	0.9300	N3—O6	1.201 (4)
C13—C14	1.380 (4)	N3—O5	1.210 (4)
C13—C18	1.513 (4)	N6—O11	1.214 (4)
C14—C15	1.380 (4)	N6—O12	1.222 (3)
C14—H14	0.9300	O4—Co1ⁱⁱ	2.0480 (19)
C15—C16	1.379 (4)	O10—Co2ⁱ	2.040 (2)
C15—N3	1.469 (4)	O13W—H13A	0.853 (10)
C16—H16	0.9300	O13W—H13B	0.850 (10)
C17—O2	1.241 (4)	O14W—H14B	0.842 (10)
C17—O1	1.249 (4)	O14W—H14C	0.849 (10)
C18—O3	1.218 (3)	O15W—H15A	0.8556
C18—O4	1.271 (3)	O15W—H15B	0.8498

N1—Co1—N2	77.82 (9)	N4—C19—H19	118.8
N1—Co1—O1	146.07 (9)	C20—C19—H19	118.8
N1—Co1—O2	88.38 (9)	C21—C20—C19	118.3 (3)
N1—Co1—O13W	93.44 (8)	C21—C20—H20	120.9
N2—Co1—O1	99.16 (9)	C19—C20—H20	120.9
N2—Co1—O2	95.02 (9)	C22—C21—C20	120.0 (3)
N2—Co1—O13W	169.57 (9)	C22—C21—H21	120.0
O2—Co1—O1	57.98 (8)	C20—C21—H21	120.0
O4ⁱ—Co1—N1	126.38 (9)	C21—C22—C23	119.3 (3)
O4ⁱ—Co1—N2	91.83 (8)	C21—C22—H22	120.3
O4ⁱ—Co1—O1	87.27 (8)	C23—C22—H22	120.3
O4ⁱ—Co1—O2	145.22 (9)	N4—C23—C22	120.8 (3)
O4ⁱ—Co1—O13W	88.80 (8)	N4—C23—C24	115.8 (2)
O13W—Co1—O1	91.28 (9)	C22—C23—C24	123.4 (3)
O13W—Co1—O2	90.36 (9)	N5—C24—C25	121.0 (3)
N4—Co2—N5	77.77 (9)	N5—C24—C23	114.8 (2)
N4—Co2—O8	88.41 (9)	C25—C24—C23	124.3 (3)
N4—Co2—O14W	95.01 (9)	C26—C25—C24	119.5 (3)
N4—Co2—O7	145.72 (9)	C26—C25—H25	120.3
N5—Co2—O7	97.17 (9)	C24—C25—H25	120.3
N5—Co2—O8	94.80 (9)	C27—C26—C25	119.5 (3)
N5—Co2—O14W	170.88 (9)	C27—C26—H26	120.2
O8—Co2—O7	57.94 (8)	C25—C26—H26	120.2
O10ⁱⁱ—Co2—N4	125.63 (9)	C26—C27—C28	118.5 (3)
O10ⁱⁱ—Co2—N5	91.14 (9)	C26—C27—H27	120.7
O10ⁱⁱ—Co2—O7	88.01 (8)	C28—C27—H27	120.7
O10ⁱⁱ—Co2—O8	145.90 (8)	N5—C28—C27	122.7 (3)
O10ⁱⁱ—Co2—O14W	88.58 (8)	N5—C28—H28	118.7
O14W—Co2—O7	91.93 (8)	C27—C28—H28	118.7
O14W—Co2—O8	90.52 (9)	C34—C29—C30	119.8 (3)
N1—C1—C2	122.7 (3)	C34—C29—C35	119.8 (3)
N1—C1—H1	118.6	C30—C29—C35	120.4 (3)
C2—C1—H1	118.6	C31—C30—C29	117.8 (3)
C1—C2—C3	119.1 (3)	C31—C30—H30	121.1
C1—C2—H2	120.4	C29—C30—H30	121.1
C3—C2—H2	120.4	C30—C31—C32	123.5 (3)
C4—C3—C2	118.6 (3)	C30—C31—N6	118.5 (3)
C4—C3—H3	120.7	C32—C31—N6	118.1 (3)
C2—C3—H3	120.7	C33—C32—C31	118.6 (3)
C3—C4—C5	119.8 (3)	C33—C32—H32	120.7
C3—C4—H4	120.1	C31—C32—H32	120.7
C5—C4—H4	120.1	C32—C33—C34	119.1 (3)
N1—C5—C4	121.2 (3)	C32—C33—C36	121.2 (3)
N1—C5—C6	115.5 (2)	C34—C33—C36	119.8 (3)
C4—C5—C6	123.2 (3)	C29—C34—C33	121.3 (3)
N2—C6—C7	121.3 (3)	C29—C34—H34	119.4
N2—C6—C5	114.6 (2)	C33—C34—H34	119.4
C7—C6—C5	124.1 (3)	O8—C35—O7	121.2 (3)
C8—C7—C6	119.8 (3)	O8—C35—C29	118.9 (3)
C8—C7—H7	120.1	O7—C35—C29	119.8 (3)
C6—C7—H7	120.1	O9—C36—O10	124.2 (3)
C9—C8—C7	119.2 (3)	O9—C36—C33	119.7 (3)
C9—C8—H8	120.4	O10—C36—C33	116.1 (3)
C7—C8—H8	120.4	C1—N1—C5	118.4 (3)
C8—C9—C10	118.5 (3)	C1—N1—Co1	124.9 (2)
C8—C9—H9	120.7	C5—N1—Co1	116.60 (18)
C10—C9—H9	120.7	C10—N2—C6	118.1 (2)
N2—C10—C9	123.1 (3)	C10—N2—Co1	126.38 (19)
N2—C10—H10	118.5	C6—N2—Co1	115.48 (18)
C9—C10—H10	118.5	O6—N3—O5	122.9 (3)
C12—C11—C16	119.3 (3)	O6—N3—C15	118.2 (3)
C12—C11—C17	120.6 (3)	O5—N3—C15	118.9 (3)
C16—C11—C17	120.0 (3)	C19—N4—C23	119.2 (3)
C11—C12—C13	121.8 (3)	C19—N4—Co2	124.7 (2)
C11—C12—H12	119.1	C23—N4—Co2	115.93 (19)
C13—C12—H12	119.1	C28—N5—C24	118.8 (3)
C14—C13—C12	119.0 (2)	C28—N5—Co2	125.7 (2)
C14—C13—C18	121.2 (2)	C24—N5—Co2	115.54 (19)
C12—C13—C18	119.8 (2)	O11—N6—O12	123.6 (3)
C13—C14—C15	118.6 (3)	O11—N6—C31	118.2 (3)
C13—C14—H14	120.7	O12—N6—C31	118.2 (3)
C15—C14—H14	120.7	C17—O1—Co1	88.4 (2)
C16—C15—C14	123.3 (3)	C17—O2—Co1	92.18 (19)
C16—C15—N3	118.3 (3)	C18—O4—Co1ⁱⁱ	116.08 (18)
C14—C15—N3	118.3 (3)	C35—O7—Co2	87.20 (19)
C15—C16—C11	118.0 (3)	C35—O8—Co2	93.42 (18)
C15—C16—H16	121.0	C36—O10—Co2ⁱ	118.16 (19)
C11—C16—H16	121.0	Co1—O13W—H13A	118 (2)
O2—C17—O1	121.3 (3)	Co1—O13W—H13B	110 (3)
O2—C17—C11	119.3 (3)	H13A—O13W—H13B	108.9 (16)
O1—C17—C11	119.4 (3)	Co2—O14W—H14B	113 (2)
O3—C18—O4	123.7 (3)	Co2—O14W—H14C	113 (3)
O3—C18—C13	119.4 (3)	H14B—O14W—H14C	110.1 (17)
O4—C18—C13	116.9 (2)	H15A—O15W—H15B	124.9
N4—C19—C20	122.4 (3)

N1—C1—C2—C3	−0.1 (6)	C9—C10—N2—Co1	179.1 (2)
C1—C2—C3—C4	1.7 (6)	C7—C6—N2—C10	1.1 (4)
C2—C3—C4—C5	−1.7 (6)	C5—C6—N2—C10	179.8 (2)
C3—C4—C5—N1	0.3 (5)	C7—C6—N2—Co1	−178.7 (2)
C3—C4—C5—C6	178.7 (3)	C5—C6—N2—Co1	0.0 (3)
N1—C5—C6—N2	−0.1 (4)	O4ⁱ—Co1—N2—C10	53.4 (2)
C4—C5—C6—N2	−178.6 (3)	N1—Co1—N2—C10	−179.7 (2)
N1—C5—C6—C7	178.6 (3)	O13W—Co1—N2—C10	146.8 (4)
C4—C5—C6—C7	0.0 (5)	O2—Co1—N2—C10	−92.4 (2)
N2—C6—C7—C8	−0.7 (4)	O1—Co1—N2—C10	−34.1 (2)
C5—C6—C7—C8	−179.2 (3)	O4ⁱ—Co1—N2—C6	−126.81 (19)
C6—C7—C8—C9	−0.1 (5)	N1—Co1—N2—C6	0.07 (19)
C7—C8—C9—C10	0.5 (5)	O13W—Co1—N2—C6	−33.5 (6)
C8—C9—C10—N2	−0.1 (5)	O2—Co1—N2—C6	87.3 (2)
C16—C11—C12—C13	−0.8 (4)	O1—Co1—N2—C6	145.66 (19)
C17—C11—C12—C13	−178.1 (2)	C16—C15—N3—O6	−16.2 (5)
C11—C12—C13—C14	0.7 (4)	C14—C15—N3—O6	166.4 (4)
C11—C12—C13—C18	179.7 (2)	C16—C15—N3—O5	165.7 (3)
C12—C13—C14—C15	0.5 (4)	C14—C15—N3—O5	−11.7 (5)
C18—C13—C14—C15	−178.5 (3)	C20—C19—N4—C23	0.2 (4)
C13—C14—C15—C16	−1.6 (4)	C20—C19—N4—Co2	174.9 (2)
C13—C14—C15—N3	175.6 (3)	C22—C23—N4—C19	0.3 (4)
C14—C15—C16—C11	1.5 (4)	C24—C23—N4—C19	179.9 (3)
N3—C15—C16—C11	−175.8 (3)	C22—C23—N4—Co2	−174.8 (2)
C12—C11—C16—C15	−0.3 (4)	C24—C23—N4—Co2	4.8 (3)
C17—C11—C16—C15	177.0 (3)	O10ⁱⁱ—Co2—N4—C19	99.1 (2)
C12—C11—C17—O2	2.6 (4)	N5—Co2—N4—C19	−178.4 (2)
C16—C11—C17—O2	−174.7 (3)	O14W—Co2—N4—C19	7.3 (2)
C12—C11—C17—O1	−179.1 (3)	O8—Co2—N4—C19	−83.1 (2)
C16—C11—C17—O1	3.7 (4)	O7—Co2—N4—C19	−93.6 (3)
C14—C13—C18—O3	178.7 (3)	O10ⁱⁱ—Co2—N4—C23	−86.1 (2)
C12—C13—C18—O3	−0.3 (4)	N5—Co2—N4—C23	−3.61 (19)
C14—C13—C18—O4	−2.9 (4)	O14W—Co2—N4—C23	−177.96 (19)
C12—C13—C18—O4	178.1 (2)	O8—Co2—N4—C23	91.7 (2)
N4—C19—C20—C21	0.1 (5)	O7—Co2—N4—C23	81.2 (2)
C19—C20—C21—C22	−1.0 (5)	C27—C28—N5—C24	−0.1 (4)
C20—C21—C22—C23	1.5 (5)	C27—C28—N5—Co2	179.0 (2)
C21—C22—C23—N4	−1.2 (4)	C25—C24—N5—C28	−0.9 (4)
C21—C22—C23—C24	179.2 (3)	C23—C24—N5—C28	179.4 (2)
N4—C23—C24—N5	−3.3 (4)	C25—C24—N5—Co2	179.9 (2)
C22—C23—C24—N5	176.3 (3)	C23—C24—N5—Co2	0.2 (3)
N4—C23—C24—C25	177.0 (3)	O10ⁱⁱ—Co2—N5—C28	−51.1 (2)
C22—C23—C24—C25	−3.3 (4)	N4—Co2—N5—C28	−177.4 (3)
N5—C24—C25—C26	0.7 (5)	O8—Co2—N5—C28	95.3 (2)
C23—C24—C25—C26	−179.6 (3)	O7—Co2—N5—C28	37.1 (2)
C24—C25—C26—C27	0.6 (5)	O10ⁱⁱ—Co2—N5—C24	128.0 (2)
C25—C26—C27—C28	−1.6 (5)	N4—Co2—N5—C24	1.76 (19)
C26—C27—C28—N5	1.4 (5)	O8—Co2—N5—C24	−85.6 (2)
C34—C29—C30—C31	0.6 (4)	O7—Co2—N5—C24	−143.82 (19)
C35—C29—C30—C31	−178.4 (2)	C30—C31—N6—O11	−167.6 (3)
C29—C30—C31—C32	−1.4 (4)	C32—C31—N6—O11	12.1 (5)
C29—C30—C31—N6	178.4 (3)	C30—C31—N6—O12	13.7 (4)
C30—C31—C32—C33	1.1 (4)	C32—C31—N6—O12	−166.5 (3)
N6—C31—C32—C33	−178.7 (2)	O2—C17—O1—Co1	3.9 (3)
C31—C32—C33—C34	0.0 (4)	C11—C17—O1—Co1	−174.4 (2)
C31—C32—C33—C36	−179.6 (3)	O4ⁱ—Co1—O1—C17	176.15 (18)
C30—C29—C34—C33	0.4 (4)	N1—Co1—O1—C17	−10.7 (3)
C35—C29—C34—C33	179.4 (2)	N2—Co1—O1—C17	−92.43 (18)
C32—C33—C34—C29	−0.7 (4)	O13W—Co1—O1—C17	87.41 (18)
C36—C33—C34—C29	178.9 (2)	O2—Co1—O1—C17	−2.21 (17)
C34—C29—C35—O8	1.0 (4)	O1—C17—O2—Co1	−4.0 (3)
C30—C29—C35—O8	−180.0 (3)	C11—C17—O2—Co1	174.3 (2)
C34—C29—C35—O7	−178.4 (3)	O4ⁱ—Co1—O2—C17	−0.6 (3)
C30—C29—C35—O7	0.7 (4)	N1—Co1—O2—C17	177.52 (19)
C32—C33—C36—O9	−179.1 (3)	N2—Co1—O2—C17	99.90 (19)
C34—C33—C36—O9	1.3 (4)	O13W—Co1—O2—C17	−89.05 (19)
C32—C33—C36—O10	2.4 (4)	O1—Co1—O2—C17	2.23 (17)
C34—C33—C36—O10	−177.2 (2)	O3—C18—O4—Co1ⁱⁱ	1.8 (4)
C2—C1—N1—C5	−1.3 (5)	C13—C18—O4—Co1ⁱⁱ	−176.55 (18)
C2—C1—N1—Co1	−178.5 (3)	O8—C35—O7—Co2	−4.4 (3)
C4—C5—N1—C1	1.3 (5)	C29—C35—O7—Co2	175.0 (2)
C6—C5—N1—C1	−177.3 (3)	O10ⁱⁱ—Co2—O7—C35	−175.39 (17)
C4—C5—N1—Co1	178.7 (2)	N4—Co2—O7—C35	14.9 (3)
C6—C5—N1—Co1	0.1 (3)	N5—Co2—O7—C35	93.71 (17)
O4ⁱ—Co1—N1—C1	−99.7 (3)	O14W—Co2—O7—C35	−86.88 (17)
N2—Co1—N1—C1	177.1 (3)	O8—Co2—O7—C35	2.53 (16)
O13W—Co1—N1—C1	−8.6 (3)	O7—C35—O8—Co2	4.6 (3)
O2—Co1—N1—C1	81.6 (3)	C29—C35—O8—Co2	−174.7 (2)
O1—Co1—N1—C1	88.8 (3)	O10ⁱⁱ—Co2—O8—C35	1.2 (3)
O4ⁱ—Co1—N1—C5	83.1 (2)	N4—Co2—O8—C35	−175.59 (19)
N2—Co1—N1—C5	−0.1 (2)	N5—Co2—O8—C35	−98.01 (19)
O13W—Co1—N1—C5	174.1 (2)	O14W—Co2—O8—C35	89.41 (18)
O2—Co1—N1—C5	−95.6 (2)	O7—Co2—O8—C35	−2.54 (17)
O1—Co1—N1—C5	−88.4 (2)	O9—C36—O10—Co2ⁱ	−4.2 (4)
C9—C10—N2—C6	−0.7 (4)	C33—C36—O10—Co2ⁱ	174.28 (17)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O13W—H13A···O7	0.85 (1)	1.99 (2)	2.741 (3)	147 (3)
O13W—H13B···O10ⁱⁱ	0.85 (1)	1.98 (2)	2.753 (3)	151 (3)
O14W—H14B···O1	0.84 (1)	2.06 (2)	2.769 (3)	142 (3)
O14W—H14C···O4ⁱ	0.85 (1)	1.92 (2)	2.715 (3)	155 (3)
O15W—H15A···O2ⁱⁱⁱ	0.86	2.28	2.833 (12)	123

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

π–π stacking interaction geometrical parameters (Å, °) top

Rings	Distence	Dihedral angle
Cg1···Cg1ⁱ	3.977 (2)	parallel
Cg2···Cg4	3.583 (2)	3.57 (5)
Cg2···Cg5	3.889 (2)	6.65 (5)
Cg3···Cg6	3.662 (2)	4.9 (1)
Cg5···Cg4^iv	3.609 (2)	3.08 (5)

Notes: Cg1 is the centroid of the ring containing N1; Cg1ⁱ is the centroid of the ring containing N1ⁱ; Cg2 is the centroid of the ring containing N2: Cg3 is the centroid of the ring containing C11; Cg4 is the centroid of the ring containing N4ⁱⁱ; Cg4^iv is the centroid of the ring containing N4^iv; Cg5 is the centroid of the ring containing N5ⁱⁱⁱ; Cg6 is the centroid of the ring containing C29^v. Symmetry codes: (i) 1-x, -y, 1-z; (ii) -1/2+x, 1/2-y, -1/2+z; (iii) 3/2-x, -1/2+y, 1/2-z; (iv) 1/2-x, -1/2+y, 1/2-z; (v) 1+x, y, z.

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