(5-Carb­oxy-1H-pyrazole-3-carboxyl­ato-κ²N²,O³)bis­(1,10-phenanthroline-κ²N,N′)cobalt(III) perchlorate 2.5-hydrate

In the title mononuclear complex, [Co(C₅H₂N₂O₄)(C₁₂H₈N₂)₂]ClO₄·2.5H₂O, the Co^III atom is in a slightly distorted octa­hedral environment, coordinated by four N atoms from two N,N′-bidentate phenanthroline ligands, and one O and one N atom of the 5-carb­oxy-1H-pyrazole-3-carboxyl­ate ligand. The mol­ecules are linked into a three-dimensional framework by O—H...O hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in solvent or counterion
• R factor = 0.044
• wR factor = 0.129
• Data-to-parameter ratio = 14.1

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 ............       0.50 Ratio
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       1.02
PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ...    5870.00 Ang-3
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT214_ALERT_2_C Atom O8'     (Anion/Solvent) ADP max/min Ratio         4.60 prola
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for       Cl1'
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      38.00 Perc.
PLAT432_ALERT_2_C Short Inter X...Y Contact  C1     ..  O8'     ..       3.00 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          5
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              H2 O

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 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
   8 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

Computing details

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(5-Carboxy-1H-pyrazole-3-carboxylato-κ²N²,O³)bis(1,10-phenanthroline- κ²N,N')cobalt(III) perchlorate 2.5-hydrate

Crystal data

[Co(C5H2N2O4)(C12H8N2)2]ClO4·2.5H2O	F(000) = 2936
Mr = 717.91	Dx = 1.625 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5351 reflections
a = 33.905 (7) Å	θ = 3.1–27.5°
b = 9.6566 (19) Å	µ = 0.75 mm^−1
c = 23.237 (5) Å	T = 295 K
β = 129.50 (3)°	Block, orange
V = 5870 (2) Å^3	0.25 × 0.20 × 0.16 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer	6717 independent reflections
Radiation source: rotating anode	5351 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
oscillation scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: ψ scan (ABSCOR; Higashi, 1995)	h = −43→43
Tmin = 0.802, Tmax = 0.866	k = −10→12
27567 measured reflections	l = −30→30

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0727P)^2 + 6.0669P] where P = (Fo^2 + 2Fc^2)/3
6717 reflections	(Δ/σ)max = 0.001
475 parameters	Δρmax = 0.46 e Å^−3
94 restraints	Δρmin = −0.51 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Co1	0.109016 (11)	0.34669 (3)	0.471185 (16)	0.03050 (11)
O1	0.05579 (9)	−0.1081 (2)	0.23233 (12)	0.0572 (5)
O2	0.08209 (11)	0.0972 (2)	0.22516 (13)	0.0699 (7)
H2O	0.0799	0.0569	0.1907	0.105*
O3	0.07052 (12)	−0.0106 (3)	0.50069 (14)	0.0779 (8)
O4	0.09101 (7)	0.21147 (19)	0.51010 (10)	0.0415 (4)
Cl1	0.21272 (15)	−0.2384 (4)	0.27623 (18)	0.0858 (10)	0.729 (10)
O5	0.2385 (2)	−0.1790 (8)	0.3466 (3)	0.128 (3)	0.729 (10)
O6	0.1657 (2)	−0.2856 (11)	0.2491 (4)	0.215 (6)	0.729 (10)
O7	0.2432 (3)	−0.3418 (6)	0.2814 (6)	0.206 (5)	0.729 (10)
O8	0.2078 (3)	−0.1346 (9)	0.2306 (4)	0.163 (4)	0.729 (10)
Cl1'	0.2063 (5)	−0.2440 (11)	0.2804 (7)	0.116 (5)	0.271 (10)
O5'	0.1791 (9)	−0.1365 (16)	0.2800 (13)	0.28 (2)	0.271 (10)
O6'	0.2548 (5)	−0.246 (3)	0.3494 (8)	0.28 (2)	0.271 (10)
O7'	0.1823 (7)	−0.3684 (13)	0.2701 (9)	0.119 (7)	0.271 (10)
O8'	0.2094 (10)	−0.2251 (19)	0.2247 (10)	0.239 (19)	0.271 (10)
O1W	0.09724 (13)	−0.0164 (3)	0.13964 (16)	0.0903 (9)
H1W1	0.0873	−0.0064	0.0958	0.135*
H1W2	0.1277	−0.0470	0.1679	0.135*
O2W	0.0000	−0.3026 (4)	0.2500	0.0686 (9)
H2W1	0.0095	−0.2501	0.2315	0.103*
O3W	0.1572 (2)	−0.1977 (6)	0.5242 (3)	0.1676 (19)
H3W1	0.1289	−0.1622	0.5082	0.251*
H3W2	0.1792	−0.1713	0.5691	0.251*
N1	0.18010 (8)	0.2888 (2)	0.53930 (11)	0.0396 (5)
N2	0.13286 (7)	0.4786 (2)	0.43646 (11)	0.0351 (4)
N3	0.11829 (8)	0.4825 (2)	0.54125 (11)	0.0360 (4)
N4	0.03916 (7)	0.4149 (2)	0.40531 (11)	0.0347 (4)
N5	0.09061 (7)	0.1982 (2)	0.34337 (11)	0.0353 (4)
N6	0.09311 (7)	0.2062 (2)	0.40291 (10)	0.0329 (4)
C1	0.20203 (12)	0.1895 (3)	0.59005 (15)	0.0537 (7)
H1	0.1822	0.1359	0.5963	0.064*
C2	0.25502 (15)	0.1632 (4)	0.63501 (17)	0.0736 (11)
H2	0.2696	0.0912	0.6695	0.088*
C3	0.28496 (13)	0.2437 (5)	0.62782 (19)	0.0754 (11)
H3	0.3200	0.2286	0.6586	0.090*
C4	0.26282 (10)	0.3476 (4)	0.57456 (18)	0.0584 (8)
C5	0.28894 (12)	0.4365 (5)	0.5591 (2)	0.0747 (12)
H5	0.3241	0.4264	0.5871	0.090*
C6	0.26492 (13)	0.5327 (4)	0.5064 (2)	0.0715 (11)
H6	0.2836	0.5878	0.4985	0.086*
C7	0.21091 (12)	0.5539 (3)	0.46138 (18)	0.0532 (7)
C8	0.18217 (14)	0.6513 (3)	0.4041 (2)	0.0607 (9)
H8	0.1980	0.7101	0.3926	0.073*
C9	0.13136 (14)	0.6593 (3)	0.36573 (18)	0.0572 (8)
H9	0.1121	0.7235	0.3274	0.069*
C10	0.10732 (11)	0.5722 (3)	0.38297 (15)	0.0451 (6)
H10	0.0722	0.5803	0.3560	0.054*
C11	0.18429 (9)	0.4685 (3)	0.47543 (14)	0.0397 (6)
C12	0.20970 (9)	0.3664 (3)	0.53114 (14)	0.0418 (6)
C13	−0.00055 (9)	0.3735 (3)	0.33684 (15)	0.0436 (6)
H13	0.0041	0.3028	0.3145	0.052*
C14	−0.04856 (10)	0.4327 (3)	0.29802 (16)	0.0515 (7)
H14	−0.0755	0.4010	0.2505	0.062*
C15	−0.05645 (10)	0.5371 (3)	0.32920 (18)	0.0543 (7)
H15	−0.0885	0.5779	0.3028	0.065*
C16	−0.01576 (10)	0.5826 (3)	0.40156 (17)	0.0461 (6)
C17	−0.01936 (13)	0.6860 (3)	0.4419 (2)	0.0595 (8)
H17	−0.0504	0.7303	0.4193	0.071*
C18	0.02128 (13)	0.7209 (3)	0.5120 (2)	0.0591 (8)
H18	0.0177	0.7891	0.5367	0.071*
C19	0.07013 (12)	0.6551 (3)	0.54977 (18)	0.0478 (6)
C20	0.11459 (14)	0.6833 (3)	0.62308 (19)	0.0587 (8)
H20	0.1140	0.7500	0.6513	0.070*
C21	0.15828 (13)	0.6131 (4)	0.65239 (17)	0.0581 (8)
H21	0.1877	0.6328	0.7006	0.070*
C22	0.15942 (11)	0.5114 (3)	0.61078 (15)	0.0472 (6)
H22	0.1896	0.4628	0.6321	0.057*
C23	0.07438 (9)	0.5534 (3)	0.51123 (14)	0.0363 (5)
C24	0.03156 (9)	0.5168 (3)	0.43747 (14)	0.0365 (5)
C25	0.06945 (10)	0.0095 (3)	0.25430 (14)	0.0436 (6)
C26	0.07430 (9)	0.0666 (3)	0.31765 (13)	0.0367 (5)
C27	0.06636 (10)	−0.0071 (3)	0.36077 (14)	0.0424 (6)
H27	0.0552	−0.0980	0.3546	0.051*
C28	0.07895 (9)	0.0863 (3)	0.41481 (13)	0.0378 (5)
C29	0.07924 (11)	0.0902 (3)	0.47853 (15)	0.0460 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Co1	0.02964 (17)	0.03625 (19)	0.02874 (17)	0.00241 (12)	0.02002 (14)	−0.00006 (12)
O1	0.0739 (14)	0.0500 (12)	0.0548 (12)	−0.0074 (11)	0.0444 (12)	−0.0109 (10)
O2	0.121 (2)	0.0549 (13)	0.0687 (14)	−0.0100 (14)	0.0763 (16)	−0.0088 (11)
O3	0.137 (2)	0.0573 (14)	0.0766 (16)	−0.0319 (15)	0.0855 (18)	−0.0110 (12)
O4	0.0532 (10)	0.0453 (10)	0.0399 (9)	−0.0024 (8)	0.0361 (9)	−0.0028 (8)
Cl1	0.0713 (12)	0.133 (2)	0.0568 (13)	−0.0318 (12)	0.0426 (12)	−0.0052 (12)
O5	0.127 (6)	0.186 (6)	0.099 (5)	−0.081 (5)	0.086 (5)	−0.065 (4)
O6	0.101 (5)	0.363 (17)	0.162 (7)	−0.140 (9)	0.075 (5)	−0.055 (9)
O7	0.170 (7)	0.121 (6)	0.301 (14)	−0.019 (5)	0.136 (9)	−0.048 (7)
O8	0.152 (6)	0.222 (10)	0.126 (6)	−0.004 (6)	0.094 (5)	0.067 (6)
Cl1'	0.126 (9)	0.158 (8)	0.095 (6)	−0.028 (5)	0.086 (6)	0.019 (5)
O5'	0.36 (4)	0.17 (2)	0.18 (2)	0.16 (3)	0.11 (3)	0.029 (18)
O6'	0.103 (13)	0.64 (7)	0.094 (15)	0.07 (3)	0.066 (12)	0.08 (3)
O7'	0.19 (2)	0.083 (9)	0.098 (11)	−0.046 (10)	0.101 (13)	−0.025 (7)
O8'	0.52 (5)	0.142 (19)	0.157 (17)	−0.11 (3)	0.27 (3)	−0.049 (15)
O1W	0.146 (3)	0.0825 (18)	0.0787 (17)	0.0101 (18)	0.088 (2)	−0.0012 (14)
O2W	0.0543 (18)	0.064 (2)	0.074 (2)	0.000	0.0343 (17)	0.000
O3W	0.182 (5)	0.193 (5)	0.158 (4)	0.033 (4)	0.123 (4)	0.049 (4)
N1	0.0380 (10)	0.0458 (12)	0.0299 (10)	0.0097 (9)	0.0192 (9)	−0.0007 (9)
N2	0.0347 (10)	0.0391 (11)	0.0345 (10)	−0.0006 (8)	0.0234 (9)	−0.0024 (8)
N3	0.0378 (10)	0.0401 (11)	0.0349 (10)	−0.0012 (9)	0.0254 (9)	−0.0031 (8)
N4	0.0304 (9)	0.0398 (11)	0.0354 (10)	0.0009 (8)	0.0218 (9)	−0.0008 (8)
N5	0.0357 (10)	0.0442 (11)	0.0317 (10)	0.0047 (9)	0.0240 (9)	0.0020 (9)
N6	0.0340 (10)	0.0387 (11)	0.0297 (9)	0.0023 (8)	0.0221 (9)	0.0004 (8)
C1	0.0557 (16)	0.0597 (18)	0.0346 (14)	0.0167 (14)	0.0235 (13)	0.0073 (12)
C2	0.067 (2)	0.082 (3)	0.0335 (15)	0.037 (2)	0.0141 (15)	0.0069 (15)
C3	0.0388 (15)	0.100 (3)	0.0524 (19)	0.0202 (18)	0.0125 (15)	−0.0167 (19)
C4	0.0315 (13)	0.075 (2)	0.0528 (17)	0.0053 (13)	0.0192 (13)	−0.0222 (15)
C5	0.0329 (14)	0.099 (3)	0.087 (3)	−0.0150 (17)	0.0357 (17)	−0.039 (2)
C6	0.0537 (19)	0.086 (3)	0.095 (3)	−0.0285 (19)	0.057 (2)	−0.041 (2)
C7	0.0545 (16)	0.0582 (18)	0.0660 (19)	−0.0205 (14)	0.0473 (16)	−0.0248 (15)
C8	0.081 (2)	0.0561 (19)	0.072 (2)	−0.0248 (17)	0.062 (2)	−0.0165 (16)
C9	0.079 (2)	0.0455 (16)	0.0543 (17)	−0.0068 (15)	0.0461 (18)	0.0022 (13)
C10	0.0502 (15)	0.0433 (15)	0.0433 (14)	0.0000 (12)	0.0305 (13)	0.0017 (11)
C11	0.0340 (12)	0.0472 (14)	0.0416 (13)	−0.0061 (10)	0.0258 (11)	−0.0151 (11)
C12	0.0305 (11)	0.0531 (16)	0.0391 (13)	−0.0003 (11)	0.0209 (11)	−0.0130 (11)
C13	0.0344 (12)	0.0524 (16)	0.0372 (13)	−0.0015 (11)	0.0197 (11)	−0.0022 (11)
C14	0.0355 (13)	0.0621 (19)	0.0435 (15)	0.0009 (12)	0.0189 (12)	0.0040 (13)
C15	0.0353 (13)	0.0605 (19)	0.0625 (18)	0.0111 (13)	0.0290 (14)	0.0141 (15)
C16	0.0415 (13)	0.0444 (15)	0.0607 (17)	0.0059 (12)	0.0364 (14)	0.0060 (13)
C17	0.0570 (18)	0.0486 (17)	0.089 (2)	0.0127 (14)	0.0535 (19)	0.0043 (16)
C18	0.072 (2)	0.0440 (16)	0.090 (2)	0.0043 (15)	0.065 (2)	−0.0066 (16)
C19	0.0611 (17)	0.0398 (14)	0.0635 (18)	−0.0044 (12)	0.0495 (16)	−0.0077 (13)
C20	0.079 (2)	0.0547 (18)	0.0622 (19)	−0.0095 (16)	0.0541 (19)	−0.0198 (15)
C21	0.0653 (19)	0.0650 (19)	0.0445 (16)	−0.0133 (16)	0.0352 (16)	−0.0200 (14)
C22	0.0448 (14)	0.0570 (17)	0.0369 (13)	−0.0019 (12)	0.0246 (12)	−0.0074 (12)
C23	0.0401 (12)	0.0352 (12)	0.0451 (13)	−0.0019 (10)	0.0325 (12)	−0.0024 (10)
C24	0.0348 (12)	0.0375 (13)	0.0450 (13)	0.0024 (10)	0.0290 (11)	0.0027 (10)
C25	0.0473 (14)	0.0458 (15)	0.0389 (13)	0.0044 (12)	0.0280 (12)	0.0005 (11)
C26	0.0333 (11)	0.0457 (14)	0.0299 (11)	0.0012 (10)	0.0195 (10)	−0.0038 (10)
C27	0.0501 (14)	0.0387 (13)	0.0420 (13)	−0.0058 (11)	0.0309 (13)	−0.0052 (11)
C28	0.0423 (13)	0.0396 (13)	0.0354 (12)	−0.0003 (10)	0.0265 (11)	0.0000 (10)
C29	0.0582 (16)	0.0465 (15)	0.0444 (14)	−0.0054 (13)	0.0379 (14)	−0.0025 (12)

Geometric parameters (Å, º)

Co1—N6	1.887 (2)	C3—H3	0.93
Co1—O4	1.8968 (18)	C4—C12	1.408 (4)
Co1—N2	1.938 (2)	C4—C5	1.434 (5)
Co1—N1	1.942 (2)	C5—C6	1.325 (6)
Co1—N4	1.943 (2)	C5—H5	0.93
Co1—N3	1.954 (2)	C6—C7	1.433 (5)
O1—C25	1.210 (3)	C6—H6	0.93
O2—C25	1.315 (3)	C7—C8	1.399 (5)
O2—H2O	0.8501	C7—C11	1.406 (4)
O3—C29	1.222 (3)	C8—C9	1.347 (5)
O4—C29	1.302 (3)	C8—H8	0.93
Cl1—O6	1.368 (5)	C9—C10	1.396 (4)
Cl1—O7	1.385 (6)	C9—H9	0.93
Cl1—O8	1.390 (5)	C10—H10	0.93
Cl1—O5	1.397 (5)	C11—C12	1.403 (4)
Cl1'—O8'	1.375 (7)	C13—C14	1.387 (4)
Cl1'—O7'	1.384 (7)	C13—H13	0.93
Cl1'—O5'	1.385 (7)	C14—C15	1.364 (4)
Cl1'—O6'	1.386 (7)	C14—H14	0.93
O1W—H1W1	0.85	C15—C16	1.404 (4)
O1W—H1W2	0.85	C15—H15	0.93
O2W—H2W1	0.85	C16—C24	1.404 (3)
O3W—H3W1	0.85	C16—C17	1.427 (4)
O3W—H3W2	0.85	C17—C18	1.345 (5)
N1—C1	1.322 (4)	C17—H17	0.93
N1—C12	1.359 (4)	C18—C19	1.438 (4)
N2—C10	1.320 (3)	C18—H18	0.93
N2—C11	1.364 (3)	C19—C23	1.396 (3)
N3—C22	1.329 (3)	C19—C20	1.408 (5)
N3—C23	1.361 (3)	C20—C21	1.354 (5)
N4—C13	1.334 (3)	C20—H20	0.93
N4—C24	1.355 (3)	C21—C22	1.396 (4)
N5—N6	1.333 (3)	C21—H21	0.93
N5—C26	1.363 (3)	C22—H22	0.93
N6—C28	1.347 (3)	C23—C24	1.416 (4)
C1—C2	1.413 (5)	C25—C26	1.480 (3)
C1—H1	0.93	C26—C27	1.388 (4)
C2—C3	1.371 (6)	C27—C28	1.375 (3)
C2—H2	0.93	C27—H27	0.93
C3—C4	1.386 (5)	C28—C29	1.475 (3)
N6—Co1—O4	84.22 (8)	C11—C7—C6	117.3 (3)
N6—Co1—N2	95.41 (8)	C9—C8—C7	119.4 (3)
O4—Co1—N2	175.42 (8)	C9—C8—H8	120.3
N6—Co1—N1	91.22 (9)	C7—C8—H8	120.3
O4—Co1—N1	91.27 (9)	C8—C9—C10	120.7 (3)
N2—Co1—N1	84.17 (9)	C8—C9—H9	119.7
N6—Co1—N4	91.61 (9)	C10—C9—H9	119.7
O4—Co1—N4	90.48 (8)	N2—C10—C9	122.0 (3)
N2—Co1—N4	94.10 (9)	N2—C10—H10	119.0
N1—Co1—N4	176.81 (9)	C9—C10—H10	119.0
N6—Co1—N3	172.58 (8)	N2—C11—C12	116.0 (2)
O4—Co1—N3	89.71 (8)	N2—C11—C7	122.8 (3)
N2—Co1—N3	90.98 (8)	C12—C11—C7	121.2 (2)
N1—Co1—N3	93.17 (9)	N1—C12—C11	116.2 (2)
N4—Co1—N3	84.17 (9)	N1—C12—C4	123.4 (3)
C25—O2—H2O	109.2	C11—C12—C4	120.4 (3)
C29—O4—Co1	115.25 (15)	N4—C13—C14	121.9 (3)
O6—Cl1—O7	112.7 (5)	N4—C13—H13	119.0
O6—Cl1—O8	110.4 (4)	C14—C13—H13	119.0
O7—Cl1—O8	107.9 (5)	C15—C14—C13	120.3 (3)
O6—Cl1—O5	110.8 (4)	C15—C14—H14	119.8
O7—Cl1—O5	108.5 (4)	C13—C14—H14	119.8
O8—Cl1—O5	106.2 (4)	C14—C15—C16	119.5 (2)
O8'—Cl1'—O7'	110.0 (6)	C14—C15—H15	120.3
O8'—Cl1'—O5'	110.0 (6)	C16—C15—H15	120.3
O7'—Cl1'—O5'	109.4 (6)	C15—C16—C24	116.8 (3)
O8'—Cl1'—O6'	110.3 (6)	C15—C16—C17	125.2 (3)
O7'—Cl1'—O6'	108.7 (6)	C24—C16—C17	118.0 (3)
O5'—Cl1'—O6'	108.4 (6)	C18—C17—C16	121.4 (3)
H1W1—O1W—H1W2	109.1	C18—C17—H17	119.3
H3W1—O3W—H3W2	106.3	C16—C17—H17	119.3
C1—N1—C12	118.6 (2)	C17—C18—C19	121.5 (3)
C1—N1—Co1	129.6 (2)	C17—C18—H18	119.2
C12—N1—Co1	111.80 (17)	C19—C18—H18	119.2
C10—N2—C11	118.0 (2)	C23—C19—C20	116.4 (3)
C10—N2—Co1	130.12 (18)	C23—C19—C18	117.9 (3)
C11—N2—Co1	111.84 (17)	C20—C19—C18	125.7 (3)
C22—N3—C23	118.5 (2)	C21—C20—C19	119.9 (3)
C22—N3—Co1	129.93 (18)	C21—C20—H20	120.0
C23—N3—Co1	111.53 (16)	C19—C20—H20	120.0
C13—N4—C24	118.3 (2)	C20—C21—C22	120.5 (3)
C13—N4—Co1	129.63 (18)	C20—C21—H21	119.8
C24—N4—Co1	112.06 (16)	C22—C21—H21	119.8
N6—N5—C26	104.44 (19)	N3—C22—C21	121.3 (3)
N5—N6—C28	111.6 (2)	N3—C22—H22	119.4
N5—N6—Co1	135.21 (17)	C21—C22—H22	119.4
C28—N6—Co1	113.18 (15)	N3—C23—C19	123.4 (2)
N1—C1—C2	121.3 (3)	N3—C23—C24	116.1 (2)
N1—C1—H1	119.4	C19—C23—C24	120.5 (2)
C2—C1—H1	119.4	N4—C24—C16	123.2 (2)
C3—C2—C1	120.0 (3)	N4—C24—C23	116.2 (2)
C3—C2—H2	120.0	C16—C24—C23	120.7 (2)
C1—C2—H2	120.0	O1—C25—O2	123.4 (2)
C2—C3—C4	119.8 (3)	O1—C25—C26	122.7 (3)
C2—C3—H3	120.1	O2—C25—C26	113.9 (2)
C4—C3—H3	120.1	N5—C26—C27	111.9 (2)
C3—C4—C12	116.9 (3)	N5—C26—C25	122.8 (2)
C3—C4—C5	126.0 (3)	C27—C26—C25	125.2 (2)
C12—C4—C5	117.1 (3)	C28—C27—C26	103.5 (2)
C6—C5—C4	122.5 (3)	C28—C27—H27	128.3
C6—C5—H5	118.8	C26—C27—H27	128.3
C4—C5—H5	118.8	N6—C28—C27	108.7 (2)
C5—C6—C7	121.5 (3)	N6—C28—C29	114.1 (2)
C5—C6—H6	119.2	C27—C28—C29	137.2 (2)
C7—C6—H6	119.2	O3—C29—O4	123.2 (2)
C8—C7—C11	117.0 (3)	O3—C29—C28	123.6 (3)
C8—C7—C6	125.7 (3)	O4—C29—C28	113.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3^i	0.85	1.91	2.756 (5)	175
O1W—H1W2···O8	0.85	2.28	3.121 (11)	173
O2—H2O···O1W	0.85	1.77	2.591 (5)	161
O2W—H2W1···O1	0.85	2.07	2.874 (4)	157
O3W—H3W1···O3	0.85	2.38	3.187 (8)	159

Symmetry code: (i) x, −y, z−1/2.